organic papers 2-[(Dimethylamino)(phenyl)methyl]benzoic acid
|
|
- Mervyn Chase
- 5 years ago
- Views:
Transcription
1 organic papers Acta Crystallographica Section E Structure Reports Online ISSN [(Dimethylamino)(phenyl)methyl]benzoic acid Yvette L. Dann, Andrew R. Cowley and Harry L. Anderson* University of Oxford, Department of Chemistry, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA, England Correspondence harry.anderson@chemistry.ox.ac.uk Key indicators Single-crystal X-ray study T = 150 K Mean (C C) = Å R factor = wr factor = Data-to-parameter ratio = 8.4 For details of how these key indicators were automatically derived from the article, see The title compound {systematic name: [(2-carboxylatophenyl)(phenyl)methyl]-N,N-dimethylammonium}, C 16 H 17 NO 2, crystallizes as a hydrogen-bonded zwitterion. Comment The title compound, (I), was prepared as described and shown in the scheme. This compound crystallizes as the zwitterion [(2-carboxylatophenyl)(phenyl)methyl]-N,N-dimethylammonium (Fig. 1). There are infinite chains of hydrogen-bonded molecules, with alternating stereochemistry at C1, running parallel to the crystallographic c axis (Fig. 2). The molecules are connected by hydrogen bonds between N1H and O1 of a neighbouring molecule [N1O1 i = (3) Å; symmetry code: (i) x; y þ 1; z 1 2 ]. There also appears to be intramolecular C1 H11O1 hydrogen bonding (Desiraju, 2005), as shown by the CO distance of (3) Å. This interaction is strengthened by the increased CH acidity due to the adjacent positively-charged N atom. Received 22 June 2005 Accepted 4 July 2005 Online 13 July 2005 # 2005 International Union of Crystallography Printed in Great Britain all rights reserved Experimental Dimethylamine (4.7 ml of a 40 wt% solution in water, 35 mmol) and 1-bromo-2-[chloro(phenyl)methyl]benzene, (II) (Katsura et al., 1997) (500 mg, 1.78 mmol), in dimethyl sulfoxide (3.8 ml) were heated at reflux for 24 h. The product was purified by column chromatography and recrystallisation from dichloromethane/light petroleum to give [(2-bromophenyl)(phenyl)methyl]-N,N-dimethylamine, (III), as a white crystalline solid (234 mg, 45%, m.p. 333 K). Butyllithium (0.86 ml of 1.6 M hexane solution, 1.38 mmol) was added dropwise to a solution of (III) (200 mg, 0.69 mmol) in anhydrous tetrahydrofuran (4 ml) at 195 K and stirred for 2 h. The reaction mixture was warmed to room temperature whilst dry carbon dioxide was bubbled through the solution for a further 2 h. Water (5 ml) and acetic acid (0.13 ml, 2.27 mmol) were added until a ph of 7 was achieved. The product was purified by column chromatography (2:25 methanol dichloromethane) to yield (I) as colourless crystals (136 mg, 77%). Crystals suitable for single-crystal X-ray diffraction analysis were obtained by slow evaporation of a solution in propan-2-ol. o2502 Dann et al. C 16 H 17 NO 2 doi: /s
2 organic papers Table 1 Selected geometric parameters (Å, ). N1 C (3) N1 C (4) N1 C (3) N1 H (3) C1 C (4) C1 N1 C (2) C1 N1 C (2) C9 N1 C (2) C1 N1 H (18) C9 N1 H (19) C10 N1 H (18) N1 C1 C (2) C1 C (4) C2 C (4) C7 C (3) C8 O (3) C8 O (3) N1 C1 C (2) C2 C1 C (2) C1 C2 C (2) C2 C7 C (2) C7 C8 O (2) C7 C8 O (2) O1 C8 O (2) Figure 1 The zwitterionic form of compound (I), showing 40% probability displacement ellipsoids and H atoms of fixed radii. Table 2 Hydrogen-bond geometry (Å, ). D HA D H HA DA D HA N1 H1O1 i 1.04 (3) 1.64 (3) (3) 176 (3) C1 H11O (3) 139 Symmetry codes: (i) x; y þ 1; z 1 2. Figure 2 View of one of the infinite hydrogen-bonded chains of (I) parallel to the c axis. The HO interactions are shown as green and white lines (CrystalMaker Software Limited, 2002). Crystal data C 16 H 17 NO 2 M r = Monoclinic, C2=c a = (10) Å b = (4) Å c = (5) Å = (2) V = (2) Å 3 Z =8 Data collection Nonius KappaCCD diffractometer! scans Absorption correction: multi-scan SCALEPACK (Otwinowski & Minor, 1997) T min = 0.97, T max = measured reflections Refinement Refinement on F R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 176 parameters D x = Mg m 3 Mo K radiation Cell parameters from 3144 reflections = 5 27 = 0.08 mm 1 T = 150 K Block, colourless mm 3079 independent reflections 1487 reflections with I > 3(I) R int = max = 27.5 h = 31! 31 k = 11! 12 l = 15! 15 H atoms treated by a mixture of independent and constrained refinement Weighting scheme: see below (/) max = max = 0.25 e Å 3 min = 0.22 e Å 3 A Chebychev polynomial (Carruthers & Watkin, 1979; Prince, 1982) was used in the weighting scheme, [weight] = 1.0/[A 0 T 0 (x) + A 1 T 1 (x) + + A n 1 T n 1 (x)], where A i are the Chebychev coefficients 0.491, and 0.192, and x = F/F max ; robust weighting (Prince, 1982) W = [weight] [1 (F/6F) 2 ] 2. The N-bound H atom was located in a difference Fourier map and its coordinates and isotropic displacement parameter subsequently refined. Other H atoms were positioned geometrically, with C H = 1.00 Å and U iso (H) = 1.2U eq (C). Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Issue 12; Betteridge et al., 2003); molecular graphics: CrystalMaker (CrystalMaker Software Limited, 2002); software used to prepare material for publication: CRYSTALS. References Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P. W., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, Carruthers, J. R. & Watkin, D. J. (1979). Acta Cryst. A35, CrystalMaker Software Limited (2002). CrystalMaker. Version 5.0. Crystal- Maker Software Limited, Begbroke Science Park, Building 5, Sandy Lane, Yarnton, Oxfordshire, OX5 1PF, England. Desiraju, G. R. (2005). Chem. Commun Katsura, Y., Zhang, X. Y., Homma, K., Rice, K. C., Calderon, S. N., Rothman, R. B., Yamamura, H. I., Davis, P., Flippen-Anderson, J. L., Xu, H., Becketts, K., Foltz, E. J. & Porreca, F. J. (1997). J. Med. Chem. 40, Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp New York: Academic Press. Prince, E. (1982). Mathematical Techniques in Crystallography and Material Science. New York: Springer-Verlag. Dann et al. C 16 H 17 NO 2 o2503
3 supporting information [ 2-[(Dimethylamino)(phenyl)methyl]benzoic acid Yvette L. Dann, Andrew R. Cowley and Harry L. Anderson [(2-carboxylatophenyl)(phenyl)methyl]-N,N-dimethylammonium Crystal data C 16 H 17 NO 2 M r = Monoclinic, C2/c a = (10) Å b = (4) Å c = (5) Å β = (2) V = (2) Å 3 Z = 8 F(000) = 1088 Data collection Nonius KappaCCD diffractometer Graphite monochromator ω scans Absorption correction: multi-scan DENZO and SCALEPACK (Otwinowski & Minor, 1997) T min = 0.97, T max = 0.99 Refinement Refinement on F Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 176 parameters 0 restraints Primary atom site location: structure-invariant direct methods Hydrogen site location: inferred from neighbouring sites D x = Mg m 3 Melting point: 446 K Mo Kα radiation, λ = Å Cell parameters from 3144 reflections θ = 5 27 µ = 0.08 mm 1 T = 150 K Block, colourless mm measured reflections 3079 independent reflections 1487 reflections with I > 3σ(I) R int = θ max = 27.5, θ min = 5.5 h = k = l = H atoms treated by a mixture of independent and constrained refinement Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A 0 *T 0 (x) + A 1 *T 1 (x) + A n-1 ]*T n-1 (x)] where A i are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF) 2 ] 2 A i are: (Δ/σ) max = Δρ max = 0.25 e Å 3 Δρ min = 0.22 e Å 3 sup-1
4 Special details Experimental. The material was prepared as described above and recrystallized from propan-2-ol. Additional spectroscopic data before recrystallization: 1 H NMR: (400.1 MHz, CDCl 3 ) 2.54(6H, s), 4.82 (1H, s), (6H, m) 7.54 (2H, d, J 7.0), 8.35 (1H, d, J 9.2) 13 C NMR: (500.3 MHz, CDCl 3 ) 42.1, 77.2, 128.9, 129.0, 129.2, 129.5, 130.5, 131.5, 134.6, 134.9, 135.7, 136.5, HR MS (ESI - ) Found (M H) -, calc Refinement. The large refined displacement parameters for the C atoms C15 and C16 and the variations in the C C bond lengths of the phenyl group containing these atoms suggest there to be some disorder of this group. Attempts to model this did not lead to any improvement is the agreement with the X-ray data and were abandoned. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq N (8) (2) (18) C (10) (3) (19) C (11) (3) (2) C (15) (3) (2) C (17) (4) (2) C (14) (3) (3) C (11) (3) (2) C (10) (3) (2) C (10) (3) (2) O (9) (2) (14) O (8) (2) (15) C (13) (3) (3) C (11) (3) (2) C (11) (3) (2) C (12) (4) (3) C (13) (4) (3) C (13) (4) (3) C (16) (8) (4) C (15) (8) (3) H (13) (4) (3) (10)* H * H * H * H * H * H * H * H * H * H * H * H * H * H * H * sup-2
5 H * Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 N (11) (12) (11) (9) (9) (9) C (14) (14) (12) (11) (10) (10) C (16) (14) (13) (12) (11) (11) C (2) (18) (14) (17) (15) (13) C (3) (19) (16) (19) (16) (14) C (2) (15) (17) (15) (16) (14) C (16) (14) (14) (12) (12) (12) C (13) (13) (12) (11) (10) (10) C (13) (14) (13) (11) (10) (11) O (13) (12) (9) (11) (9) (9) O (13) (11) (10) (9) (9) (9) C (19) (16) (18) (14) (14) (13) C (15) (16) (14) (12) (11) (12) C (15) (16) (14) (13) (12) (12) C (18) (2) (18) (16) (14) (16) C (17) (2) (2) (16) (15) (19) C (17) (2) (2) (16) (15) (18) C (2) (7) (2) (3) (18) (4) C (2) (7) (2) (3) (16) (3) Geometric parameters (Å, º) N1 C (3) C8 O (3) N1 C (4) C9 H N1 C (3) C9 H N1 H (3) C9 H C1 C (4) C10 H C1 C (4) C10 H C1 H C10 H C2 C (4) C11 C (4) C2 C (4) C11 C (5) C3 C (5) C12 C (5) C3 H C12 H C4 C (5) C13 C (5) C4 H C13 H C5 C (4) C14 C (5) C5 H C14 H C6 C (4) C15 C (5) C6 H C15 H C7 C (3) C16 H C8 O (3) C1 N1 C (2) O1 C8 O (2) sup-3
6 C1 N1 C (2) N1 C9 H C9 N1 C (2) N1 C9 H C1 N1 H (18) H91 C9 H C9 N1 H (19) N1 C9 H C10 N1 H (18) H91 C9 H N1 C1 C (2) H92 C9 H N1 C1 C (2) N1 C10 H C2 C1 C (2) N1 C10 H N1 C1 H H101 C10 H C2 C1 H N1 C10 H C11 C1 H H101 C10 H C1 C2 C (2) H102 C10 H C1 C2 C (2) C1 C11 C (2) C3 C2 C (3) C1 C11 C (2) C2 C3 C (3) C12 C11 C (3) C2 C3 H C11 C12 C (3) C4 C3 H C11 C12 H C3 C4 C (3) C13 C12 H C3 C4 H C12 C13 C (3) C5 C4 H C12 C13 H C4 C5 C (3) C14 C13 H C4 C5 H C13 C14 C (3) C6 C5 H C13 C14 H C5 C6 C (3) C15 C14 H C5 C6 H C14 C15 C (4) C7 C6 H C14 C15 H C2 C7 C (2) C16 C15 H C2 C7 C (2) C11 C16 C (3) C6 C7 C (2) C11 C16 H C7 C8 O (2) C15 C16 H C7 C8 O (2) Hydrogen-bond geometry (Å, º) D H A D H H A D A D H A N1 H1 O1 i 1.04 (3) 1.64 (3) (3) 176 (3) C1 H11 O (3) 139 Symmetry code: (i) x, y+1, z 1/2. sup-4
Methyl acetoacetate at 150 K. The crystal structure of methyl acetoacetate, C 5 H 8 O 3, at 150 K contains discrete molecules.
organic papers Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Methyl acetoacetate at 150 K Howard A. Shallard-Brown,* David J. Watkin and Andrew R. Cowley Chemical Crystallography
More informationorganic papers Acetone (2,6-dichlorobenzoyl)hydrazone: chains of p-stacked hydrogen-bonded dimers Comment Experimental
organic papers Acta Crystallographica Section E Structure Reports Online Acetone (2,6-dichlorobenzoyl)hydrazone: chains of p-stacked hydrogen-bonded dimers ISSN 1600-5368 Solange M. S. V. Wardell, a Marcus
More informationSodium 3,5-dinitrobenzoate
metal-organic papers Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Helen P. Jones,* Amy L. Gillon and Roger J. Davey Colloids, Crystals and Interfaces Group, School of Chemical
More informationorganic papers 2-Iodo-4-nitro-N-(trifluoroacetyl)aniline: sheets built from iodo nitro and nitro nitro interactions
organic papers Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 2-Iodo-4-nitro-N-(trifluoroacetyl)aniline: sheets built from iodo nitro and nitro nitro interactions Simon J. Garden,
More informationData collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 4-(2,3-Dimethylphenyl)piperazin-1-ium chloride monohydrate Data collection Nonius KappaCCD diffractometer Absorption
More informationDiammonium biphenyl-4,4'-disulfonate. Author. Published. Journal Title DOI. Copyright Statement. Downloaded from. Link to published version
Diammonium biphenyl-4,4'-disulfonate Author Smith, Graham, Wermuth, Urs, Healy, Peter Published 2008 Journal Title Acta Crystallographica. Section E: Structure Reports Online DOI https://doi.org/10.1107/s1600536807061995
More informationRefinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 63 parameters
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Urea N,N-dimethylacetamide (1/1) Refinement R[F 2 >2(F 2 )] = 0.050 wr(f 2 ) = 0.150 S = 0.89 939 reflections
More informationOrthorhombic, Pbca a = (3) Å b = (15) Å c = (4) Å V = (9) Å 3. Data collection. Refinement
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 N 0 -(3,4-Dimethylbenzylidene)furan-2- carbohydrazide Yu-Feng Li a and Fang-Fang Jian b * a Microscale Science
More information= (3) V = (4) Å 3 Z =4 Mo K radiation. Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = 1.
Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 4,4-Diacetylheptanedinitrile Guo-wei Wang, a Jian Zhang, a Ling-hua Zhuang, b Wen-yuan Wu b and Jin-tang Wang b * a Department of
More informationorganic papers Malonamide: an orthorhombic polymorph Comment
organic papers Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Malonamide: an orthorhombic polymorph Gary S. Nichol and William Clegg* School of Natural Sciences (Chemistry), Bedson
More information= (8) V = (8) Å 3 Z =4 Mo K radiation. Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 1-(3-Amino-1H-inden-2-yl)ethanone Dong-Yue Hu and Zhi-Rong Qu* Ordered Matter Science Research Center, College
More informationRefinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 155 parameters 10 restraints
inorganic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Terbium(III) hydrogendiphosphate(v) tetrahydrate Refinement R[F 2 >2(F 2 )] = 0.011 wr(f 2 ) = 0.034 S = 1.21
More informationZ =8 Mo K radiation = 0.35 mm 1. Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 4-Amino-3-(4-pyridyl)-1,2,4-triazole- 5(4H)-thione Fang Zou, Wei-Min Xuan, Xue-Ming Fang and Hui Zhang* State
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Chlorido[N 0 -(2-oxidobenzilidene)- acetohydrazide-j 2 O,N 0,O 0 ]copper(ii) dihydrate Farba Bouyagui Tamboura,
More information= (1) V = (12) Å 3 Z =4 Mo K radiation. Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 S-Benzylisothiouronium nitrate P. Hemalatha a and V. Veeravazhuthi b * a Department of Physics, PSG College of
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Dichloridotris(trimethylphosphine)- nickel(ii) Ruixia Cao, Qibao Wang and Hongjian Sun* School of Chemistry
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Poly[tetra-l-cyanido-dipyridinecadmium(II)zinc(II)] Sheng Li,* Kun Tang and Fu-Li Zhang College of Medicine,
More informationorganic papers 2,6-Diamino-3,5-dinitro-1,4-pyrazine 1-oxide Comment
organic papers Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 2,6-Diamino-3,5-dinitro-1,4-pyrazine 1-oxide Richard D. Gilardi a * and Ray J. Butcher b a Laboratory for the Structure
More informationExperimental. Crystal data. C 18 H 22 N 4 O 6 M r = Monoclinic, P2=n a = (5) Å b = (4) Å c = (5) Å = 104.
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Ethyl 5-((1E)-1-{(E)-2-[1-(4-ethoxycarbonyl-3-methyl-1,2-oxazol-5-yl)ethylidene]hydrazin-1-ylidene}ethyl)-3- methyl-1,2-oxazole-4-carboxylate
More informationb = (13) Å c = (13) Å = (2) V = (19) Å 3 Z =2 Data collection Refinement
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 b = 12.4861 (13) Å c = 12.9683 (13) Å = 90.748 (2) V = 1051.10 (19) Å 3 Z =2 Mo K radiation = 3.87 mm 1 T = 193
More informationRapid Cascade Synthesis of Poly-Heterocyclic Architectures from Indigo
S1 Rapid Cascade Synthesis of Poly-Heterocyclic Architectures from Indigo Alireza Shakoori 1, John B. Bremner 1, Anthony C. Willis 2, Rachada Haritakun 3 and Paul A. Keller 1 * 1 School of Chemistry, University
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 2-Oxo-1,2-dihydropyrimidin-3-ium di-l- chlorido-bis{dichloridobis[pyrimidin- 2(1H)-one-jN 3 ]cuprate(ii)}
More informationData collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 92 parameters
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 1,1 0 -(Butane-1,4-diyl)dipyridinium dibromide dihydrate Ming-Qiang Wu, a Xin Xiao, a Yun-Qian Zhang, a * Sai-Feng
More informationinorganic compounds Chromous hydrazine sulfate
inorganic compounds Acta Crystallographica Section C Crystal Structure Communications ISSN 0108-2701 Chromous hydrazine sulfate Adrian W. Parkins,* Paul D. Prince, Robert A. L. Smith and Jonathan W. Steed
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Bis(3-benzoyl-1,1-di-sec-butylthioureatoj 2 O,S)palladium(II) N. Selvakumaran, a R. Karvembu, a Seik Weng
More informationZ =4 Mo K radiation = 0.17 mm 1. Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 205 parameters
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 The energetic double salt nitroguanidinium nitrate guanidinium nitrate (1/1) Georg Steinhauser, a Margaret-Jane
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 = 86.130 (2) = 81.155 (2) = 76.289 (3) V = 699.69 (4) Å 3 Z =2 Mo K radiation = 1.58 mm 1 T = 293 (2) K
More informationData collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 3-Carbamoylquinoxalin-1-ium chloride James K. Harper, a * Gary Strobel b and Atta M. Arif c a University of Central
More information(+-)-3-Carboxy-2-(imidazol-3-ium-1-yl)- propanoate
From the SelectedWorks of Kraig A. Wheeler 2009 (+-)-3-Carboxy-2-(imidazol-3-ium-1-yl)- propanoate Sara A. Reeb, Eastern Illinois University Marlesa C. Shields, Eastern Illinois University Kraig A. Wheeler,
More informationN-[(Diphenylamino)methyl]acetamide
Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Editors: W. Clegg and D. G. Watson N-[(Diphenylamino)methyl]acetamide Ganesan Venkatesa Prabhu, Nagarajan Vembu, Loganathan Muruganandam
More informationb = (9) Å c = (7) Å = (1) V = (16) Å 3 Z =4 Data collection Refinement
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 8-Iodoquinolinium triiodide tetrahydrofuran solvate Jung-Ho Son and James D. Hoefelmeyer* Department of Chemistry,
More information2-Methoxy-1-methyl-4-nitro-1H-imidazole
University of Wollongong Research Online Australian Institute for Innovative Materials - Papers Australian Institute for Innovative Materials 2007 2-Methoxy-1-methyl-4-nitro-1H-imidazole Maciej Kubicki
More informationAnhydrous Polymorphs of Theophylline: The stable Form IV consists of dimer pairs, and the metastable Form I consists of H-bonded chains
Anhydrous Polymorphs of Theophylline: The stable Form IV consists of dimer pairs, and the metastable Form I consists of H-bonded chains Dikshitkumar Khamar, a Robin Gavin Pritchard, b Ian James Bradshaw,
More informationA thermoreversible supramolecular polyurethane with excellent healing ability at 45 ºC
A thermoreversible supramolecular polyurethane with excellent healing ability at 45 ºC Antonio Feula, a Alexander Pethybridge, a Ioannis Giannakopoulos, b Xuegang Tang, b Ann M. Chippindale, a Clive R.
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Diaquabis[bis(pyrazin-2-yl) sulfide-jn 4 ]- bis(thiocyanato-jn)iron(ii) monohydrate Susanne Wöhlert,* Inke
More informationData collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 245 parameters 2 restraints
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Guanidinium phenylarsonate guanidine water (1/1/2) Graham Smith* and Urs D. Wermuth Faculty of Science and Technology,
More informationPrakash S Nayak, B. Narayana, Jerry P. Jasinski, H. S. Yathirajan and Manpreet Kaur
Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 N-(1,3-Benzothiazol-2-yl)acetamide Prakash S Nayak, B. Narayana, Jerry P. Jasinski, H. S. Yathirajan and Manpreet Kaur This open-access
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Sodium 2-mercaptoethanesulfonate monohydrate (coenzyme M sodium salt monohydrate) Stefan Mayr, a Detlef
More informationCIF access. Redetermination of biphenylene at 130K. R. Boese, D. Bläser and R. Latz
CIF access Acta Cryst. (1999). C55, IUC9900067 [ doi:10.1107/s0108270199099163 ] Redetermination of biphenylene at 130K R. Boese, D. Bläser and R. Latz Abstract Biphenylene is one of the key compounds
More informationorganic compounds 2-(3-Nitrophenylaminocarbonyl)- benzoic acid: hydrogen-bonded sheets of R 4 4 (22) rings Comment
organic compounds Acta Crystallographica Section C Crystal Structure Communications ISSN 0108-2701 2-(3-Nitrophenylaminocarbonyl)- benzoic acid: hydrogen-bonded sheets of R 4 4 (22) rings Christopher Glidewell,
More information3-methoxyanilinium 3-carboxy-4-hydroxybenzenesulfonate dihydrate.
3-methoxyanilinium 3-carboxy-4-hydroxybenzenesulfonate dihydrate. Author Smith, Graham, D. Wermuth, Urs, Healy, Peter Published 2006 Journal Title Acta crystallographica. Section E, Structure reports online
More informationWhite Phosphorus is Air-Stable Within a Self-Assembled Tetrahedral Capsule
www.sciencemag.org/cgi/content/full/324/5935/1697/dc1 Supporting Online Material for White Phosphorus is Air-Stable Within a Self-Assembled Tetrahedral Capsule Prasenjit Mal, Boris Breiner, Kari Rissanen,
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 catena-poly[[diaquamanganese(ii)]- l-pyridine-2,4,6-tricarboxylatoj 5 N,O 2,O 6 :O 4,O 40 ] Da-Wei Fu and
More informationAnion binding vs deprotonation in colorimetric pyrrolylamido(thio)urea based anion sensors
Anion binding vs deprotonation in colorimetric pyrrolylamido(thio)urea based anion sensors Louise S. Evans, ilip A. Gale *, Mark E. Light and Roberto Quesada * School of Chemistry, University of Southampton,
More informationExperimental. Crystal data. C 18 H 18 N 2 O 4 S M r = Monoclinic, P2 1 =n a = (3) Å b = (2) Å c = (5) Å = 104.
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 N-(2,3-Dimethylphenyl)-4-hydroxy-2- methyl-2h-1,2-benzothiazine-3- carboxamide 1,1-dioxide Waseeq Ahmad Siddiqui,
More informationA Straightforward Access to Stable, 16 Valence-electron Phosphine-Stabilized Fe 0 Olefin Complexes and their Reactivity
A Straightforward Access to Stable, 16 Valence-electron Phosphine-Stabilized Fe 0 Olefin Complexes and their Reactivity Benjamin Burcher, [a] Kevin J. Sanders, [b] Ladislav Benda, [b] Guido Pintacuda,
More informationV = (14) Å 3 Z =8 Cu K radiation. Data collection. Refinement
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 (E)-4-Amino-N-(1,2-dihydropyridin-2-ylidene)benzenesulfonamide nitromethane monosolvate Mostafa M. Ghorab, a Mansour
More informationReactivity of Diiron Imido Complexes
One-electron Oxidation Chemistry and Subsequent Reactivity of Diiron Imido Complexes Subramaniam Kuppuswamy, Tamara M. Powers, Bruce M. Johnson, Carl K. Brozek, Jeremy P. Krogman, Mark W. Bezpalko, Louise
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Tetraaquabis(nicotinamide-jN 1 )nickel(ii) bis(2-fluorobenzoate) Tuncer Hökelek, a * Hakan Dal, b Barış
More informationaddenda and errata [N,N 0 -Bis(4-bromobenzylidene)-2,2-dimethylpropane-j Corrigendum Reza Kia, a Hoong-Kun Fun a * and Hadi Kargar b
addenda and errata Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 [N,N 0 -Bis(4-bromobenzylidene)-2,2-dimethylpropane-j 2 N,N 0 ]iodidocopper(i). Corrigendum Reza Kia, a Hoong-Kun
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 [1-(5-Bromo-2-oxidobenzylidene)thiosemicarbazidato-j 3 O,N 1,S](pyridinejN)nickel(II) Fernanda Rosi Soares
More informationelectronic reprint 3,5-Di-p-toluoyl-1,2-dideoxy-fi-1-(imidazol-1-yl)-D-ribofuranose Nicole Düpre, Wei-Zheng Shen, Pablo J. Sanz Miguel and Jens Müller
Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Editors: W. Clegg and D. G. Watson 3,5-Di-p-toluoyl-1,2-dideoxy-fi-1-(imidazol-1-yl)-D-ribofuranose Nicole Düpre, Wei-Zheng Shen,
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 A binuclear cobalt(ii) complex of an NO 3 -donor Schiff base derived from 3-carboxylsalicylaldehyde and
More information= 0.09 mm 1 T = 294 (2) K. Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 5-(3-Methoxyphenethyl)-4-(2-methoxyphenyl)-4H-1,2,4-triazol-3-ol = 0.09 mm 1 T = 294 (2) K Data collection Bruker
More informationelectronic reprint 2-Hydroxy-3-methoxybenzaldehyde (o-vanillin) revisited David Shin and Peter Müller
Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Editors: W.T. A. Harrison, H. Stoeckli-Evans, E. R.T. Tiekink and M. Weil 2-Hydroxy-3-methoxybenzaldehyde (o-vanillin) revisited
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Di-l-bromido-bis[benzyl(diethyl ether)- magnesium] Mark A. Nesbit, Danielle L. Gray and Gregory S. Girolami*
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Aqua(2,9-dimethyl-1,10-phenanthrolinej 2 N,N 0 )diformato-j 2 O,O 0 ;jo-nickel(ii) monohydrate Ping Xia,
More informationSynthesis and Diels Alder Reactivity of Substituted [4]Dendralenes. Table of Contents
Supporting Information for: Synthesis and Diels Alder Reactivity of Substituted [4]Dendralenes Mehmet F. Saglam, Ali R. Alborzi, Alan D. Payne, Anthony C. Willis,, Michael N. Paddon- Row and Michael S.
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 b = 8.2387 (7) Å c = 14.7510 (13) Å = 106.1050 (10) V = 1987.5 (3) Å 3 Z =4 Mo K radiation = 2.78 mm 1 T
More informationSupporting Information. Chiral phosphonite, phosphite and phosphoramidite η 6 -areneruthenium(ii)
Supporting Information Chiral phosphonite, phosphite and phosphoramidite η 6 -areneruthenium(ii) complexes: application to the kinetic resolution of allylic alcohols. Mariano A. Fernández-Zúmel, Beatriz
More informationData collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 (2-Methoxy-1,3-phenylene)diboronic acid Marek Dąbrowski, Sergiusz Luliński* and Janusz Serwatowski Warsaw University
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 trans-dichloridobis(3,5-dimethylpyridine-jn)(ethanolato-jo)oxidorhenium(v) Anna Skarżyńska, Anna M. Trzeciak
More informationb = (2) Å c = (3) Å = (10) V = (2) Å 3 Z =2 Data collection Refinement
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Benznidazole José Lamartine Soares-Sobrinho, a Marcílio S. S. Cunha- Filho, b Pedro José Rolim Neto, a Juan J.
More informationSupporting Information
Remarkably Variable Reaction Modes of Frustrated Lewis Pairs with Non-Conjugated Terminal Diacetylenes Chao Chen, Roland Fröhlich, Gerald Kehr, Gerhard Erker Organisch-Chemisches Institut, Westfälische
More informationExperimental. Crystal data
electronic papers Acta Crystallographica Section C Crystal Structure Communications ISSN 0108-2701 catena-poly[fac-trichloromethyltin(iv)-l-[meso-1,2-bis(phenylsulfinyl)ethane-o:o 0 ]] Maria Teresa do
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 (Formato-jO)bis(1,10-phenanthrolinej 2 N,N 0 )copper(ii) formate hexahydrate Wei Xu,* Jian-Li Lin, Hong-Zhen
More informationReversible dioxygen binding on asymmetric dinuclear rhodium centres
Electronic Supporting Information for Reversible dioxygen binding on asymmetric dinuclear rhodium centres Takayuki Nakajima,* Miyuki Sakamoto, Sachi Kurai, Bunsho Kure, Tomoaki Tanase* Department of Chemistry,
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 l-bromido-dibromido-l-hydroxido- bis[(4s)-2-halo-6-(4-isopropyl-4,5- dihydrooxazol-2-yl)pyridine]dicopper(ii)
More information4-(4-Hydroxymethyl-1H-1,2,3-triazol-1-yl)benzoic acid
University of Malaya From the SelectedWorks of Hairul Anuar Bin Tajuddin 2011 4-(4-Hydroxymethyl-1H-1,2,3-triazol-1-yl)benzoic acid Hairul Anuar Bin Tajuddin, University of Malaya Available at: https://works.bepress.com/hairulanuar_tajuddin/6/
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Bis{tris[3-(2-pyridyl)-1H-pyrazole]- zinc(ii)} dodecamolybdosilicate hexahydrate Xiutang Zhang, a,b * Peihai
More informationInternational Journal of Innovative Research in Science, Engineering and Technology. (An ISO 3297: 2007 Certified Organization)
ISSN(Online) 2319-8753 ISSN (Print) 2347-6710 (An ISO 3297 2007 Certified Organization) Website www.ijirset.com X-Ray Crystallographic Investigation and Crystal Structure of 6-(2-Hydroxy-4,6- dimethyl-phenyl)-4-(2-methoxy-phenyl)5-
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Bis[l-1,4-bis(4,5-dihydro-1H-imidazol- 2-yl)benzene-j 2 N 3 :N 30 ]silver(i) dinitrate dihydrate Hua Sun,
More informationA two-dimensional Cd II coordination polymer: poly[diaqua[l 3-5,6-bis(pyridin-2-yl)pyrazine-2,3- dicarboxylato-j 5 O 2 :O 3 :O 3,N 4,N 5 ]cadmium]
research communications ISSN 2056-9890 A two-dimensional Cd II coordination polymer: poly[diaqua[l 3-5,6-bis(pyridin-2-yl)pyrazine-2,3- dicarboxylato-j 5 O 2 :O 3 :O 3,N 4,N 5 ]cadmium] Monserrat Alfonso
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Poly[ethylenediaminium [di-l-aqua-(l 6 - benzene-1,2,4,5-tetracarboxylatoj 10 O 1,O 10 :O 2,O 20 :O 20 :O
More informationSupporting Information
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2015 Stereoselective coordination: a six-membered P,N-chelate tailored for asymmetric allylic
More informationPhosphirenium-Borate Zwitterion: Formation in the 1,1-Carboboration Reaction of Phosphinylalkynes. Supporting Information
Phosphirenium-Borate Zwitterion: Formation in the 1,1-Carboboration Reaction of Phosphinylalkynes Olga Ekkert, Gerald Kehr, Roland Fröhlich and Gerhard Erker Supporting Information Experimental Section
More informationManganese-Calcium Clusters Supported by Calixarenes
Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 2014 Manganese-Calcium Clusters Supported by Calixarenes Rebecca O. Fuller, George A. Koutsantonis*,
More informationData collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 106 parameters 2 restraints
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 2,4-Difluorophenylboronic acid Patricia Rodríguez-Cuamatzi, a Hugo Tlahuext b and Herbert Höpfl b * a Universidad
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Propane-1,2-diammonium bis(pyridine- 2,6-dicarboxylato-j 3 O,N,O 0 )nickelate(ii) tetrahydrate Hossein Aghabozorg,
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 l-oxido-bis[hydridotris(trimethylphosphane-jp)iridium(iii)](ir Ir) bis(tetrafluoridoborate) dihydrate Joseph
More informationZiessel a* Supporting Information (75 pages) Table of Contents. 1) General Methods S2
S1 Chemistry at Boron: Synthesis and Properties of Red to Near-IR Fluorescent Dyes based on Boron Substituted Diisoindolomethene Frameworks Gilles Ulrich, a, * Sebastien Goeb a, Antoinette De Nicola a,
More informationA new synthetic route towards heterometallic 3d-3d and 3d-4f Single- Molecule Magnets. First Co II -Mn III heterometallic complex
Supplementary Information for A new synthetic route towards heterometallic 3d-3d and 3d-4f Single- Molecule Magnets. First Co II -Mn III heterometallic complex Guilherme P. Guedes,, Stéphane Soriano, Luiza
More information2-(2 -pyridyl)-4,6-diphenylphosphinine versus 2-(2 -pyridyl)-4,6- diphenylpyridine: An evaluation of their coordination chemistry towards Rh(I)
Supplementary Material (ESI) for New Journal of Chemistry This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2010 2-(2 -pyridyl)-4,6-diphenylphosphinine
More informationCoordination Behaviour of Calcocene and its Use as a Synthon for Heteroleptic Organocalcium Compounds
Supporting Information Coordination Behaviour of Calcocene and its Use as a Synthon for Heteroleptic Organocalcium Compounds Reinald Fischer, Jens Langer, Sven Krieck, Helmar Görls, Matthias Westerhausen*
More informationSpontaneous racemic resolution towards control of molecular recognition nature
This journal is The Royal Society of Chemistry 13 Supplementary Information Spontaneous racemic resolution towards control of molecular recognition nature Agata Białońska * and Zbigniew Ciunik Faculty
More information2-(3-Chloro-4-hydroxylphenyl)-N-(3,4- dimethyoxyphenethyl)acetamide. Author. Published. Journal Title DOI. Copyright Statement.
2-(3-Chloro-4-hydroxylphenyl)-N-(3,4- dimethyoxyphenethyl)acetamide Author Davis, Rohan, Healy, Peter Published 2008 Journal Title Acta Crystallographica. Section E: Structure reports online DOI https://doi.org/10.1107/s1600536808013299
More informationData collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 184 parameters 1 restraint
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 2-(4-Amino-5-thioxo-4,5-dihydro-1H- 1,2,4-triazol-3-ylmethyl)isoindoline-1,3- dione Uzma Yunus, a Mohammad Kalim
More informationmetal-organic papers Bis[1,1,3,3-tetramethyl-1,3-bis(dichloroacetato)distannoxane]
metal-organic papers Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Bis[1,1,3,3-tetramethyl-1,3-bis(dichloroacetato)distannoxane] Mostafa M. Amini, a Shabnam Hossein Abadi, a
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 l-cyanido-j 2 C:N-dicyanido-j 2 C-bis(Nethylethylenediamine-j 2 N,N 0 )copper(ii)- copper(i) Peter W. R.
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Di-l-bromido-bis({bis[2-(2-pyridyl)- ethyl]amine}copper(ii)) bis(perchlorate) Ray J. Butcher,* Yilma Gultneh,
More information2. Experimental Crystal data
data reports ISSN 2056-9890 Crystal structure of (E)-2-[1-(benzo[d]- [1,3]dioxol-5-yl)ethylidene]-N-methylhydrazine-1-carbothioamide Adriano Bof de Oliveira, a * Christian Näther, b Inke Jess, b Renan
More informationmetal-organic papers Di-l-pyridyl-1:2j 2 N:C 2 ;2:1j 2 N:C 2 -l-tetrahydrofuran-j magnesium(ii)] tetrahydrofuran hemisolvate
metal-organic papers Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Di-l-pyridyl-1:2j 2 N:C 2 ;2:1j 2 N:C 2 -l-tetrahydrofuran-j 2 O:O-bis[bromo(tetrahydrofuran)- magnesium(ii)]
More informationFormation and Properties of Cyclo[6]pyrrole and Cyclo[7]pyrrole.
Formation and Properties of Cyclo[6]pyrrole and Cyclo[7]pyrrole. Thomas Köhler, Daniel Seidel, Vincent Lynch, Forrest O. Arp, Zhongping Ou, Karl M. Kadish, * and Jonathan L. Sessler *. Department of Chemistry
More informationmetal-organic compounds
metal-organic compounds Acta Crystallographica Section C Crystal Structure Communications ISSN 0108-2701 [Sm(NO 3 ) 3 (TPTZ)(H 2 O)]2H 2 O [TPTZ is 2,4,6-tris(2-pyridyl)-1,3,5-triazine] Michael G. B. Drew,
More informationSupporting Information
Supporting Information Wiley-VCH 2007 69451 Weinheim, Germany Carbene Activation of P 4 and Subsequent Derivatization Jason D. Masuda, Wolfgang W. Schoeller, Bruno Donnadieu, and Guy Bertrand * [*] Dr.
More informationEthylenediaminium pyridine-2,5-dicarboxylate dihydrate
Ethylenediaminium pyridine-2,5-dicarboxylate dihydrate Author Smith, Graham, D. Wermuth, Urs, Young, David, Healy, Peter Published 2006 Journal Title Acta crystallographica. Section E, Structure reports
More informationComparison of the Electronic Properties of Diarylamido-Based PNZ Pincer Ligands: Redox Activity at the Ligand and Donor Ability Towards the Metal
Supporting Information Comparison of the Electronic Properties of Diarylamido-Based PNZ Pincer Ligands: Redox Activity at the Ligand and Donor Ability Towards the Metal Jillian J. Davidson 1, Jessica C.
More information1,2-Dimethyl-4,5-diphenylbenzene determined on a Bruker SMART X2S benchtop crystallographic system
University of New Hampshire University of New Hampshire Scholars' Repository Chemistry Scholarship Chemistry 4-30-2009 1,2-Dimethyl-4,5-diphenylbenzene determined on a Bruker SMART X2S benchtop crystallographic
More informationData collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections
organic compounds Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Ethyl 2-(tert-butoxycarbonylamino)-1,3- benzothiazole-6-carboxylate Can Lei, a Xin Fang, a Hai-Yang Yu, a Ming-Dong
More informationorganic papers Zwitterionic 2-(methylamino)ethanesulfonic acid
organic papers Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368 Zwitterionic 2-(methylamino)ethanesulfonic acid John A. Kalaitzis, Priscila de Almeida Leone, Ronald J. Quinn and
More information