Data collection. Refinement. R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections
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1 organic compounds Acta Crystallographica Section E Structure Reports Online ISSN Ethyl 2-(tert-butoxycarbonylamino)-1,3- benzothiazole-6-carboxylate Can Lei, a Xin Fang, a Hai-Yang Yu, a Ming-Dong Huang b and Jun-Dong Wang a * Data collection Rigaku Saturn 724 CCD areadetector diffractometer Absorption correction: numerical (NUMABS; Higashi, 2000) T min = 0.987, T max = Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 6644 measured reflections 3469 independent reflections 2412 reflections with I > 2(I) R int = parameters H-atom parameters constrained max = 0.26 e Å 3 min = 0.30 e Å 3 a College of Chemistry and Chemical Engineering, Fuzhou University, Fuzhou , People s Republic of China, and b Fujian Institute of Research on the Structure of Matter, State Key Laboratory of Structural Chemistry, Chinese Academy of Sciences, Fuzhou , People s Republic of China Correspondence wangjd@fzu.edu.cn Received 22 February 2010; accepted 18 March 2010 Key indicators: single-crystal X-ray study; T = 293 K; mean (C C) = Å; R factor = 0.088; wr factor = 0.203; data-to-parameter ratio = In the crystal of the title compound, C 15 H 18 N 2 O 4 S, inversion dimers are formed by intermolecular N HN hydrogen bonds and weak C HO contacts. These dimers stack up along [100] through inversion-related interactions between thiazole rings [centroid centroid distance = (2) Å] and the thiazole and benzene rings [centroid centroid distance = (2) Å] and C H contacts. Related literature For benzothiazole derivatives with anti-tumor activity, see: Brantley et al. (2004); Ćaleta et al. (2009); Mortimer et al. (2006) and for anti-tuberculous benzothiazolines, see: Palmer et al. (1971). For related benzothiazole structures, see: Lynch et al. (2002); Matković-Čalogović et al. (2003). Table 1 Hydrogen-bond geometry (Å, ). Cg2 is the centroid of the C7 C12 benzene ring. D HA D H HA DA D HA N1 H1N2 i (14) 162 C8 H8O1 i (14) 164 C14 H14ACg2 ii (18) 149 Symmetry codes: (i) x 1; y þ 2; z þ 2; (ii) x þ 1; y; z. Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009). The authors gratefully acknowledge the financial support from Fujian Institute of Research on the Structure of Matter, State Key Laboratory of Structural Chemistry, Chinese Academy of Sciences (Nos. SZD08003 and NSFC ). Fujian Natural Science Foundation (No J0330) and Fujian Terms of Science and Technology (Nos F5033, 2008 J1005 and 2009I0016). Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2244). Experimental Crystal data C 15 H 18 N 2 O 4 S M r = Triclinic, P1 a = (13) Å b = (2) Å c = (2) Å = (3) = (3) = (3) V = (3) Å 3 Z =2 Mo K radiation = 0.22 mm 1 T = 293 K mm References Brantley, E., Trapani, V., Alley, M. C., Hose, C. D., Bradshaw, T. D., Stevens, M. F. G., Sausville, E. A. & Stinson, S. F. (2004). Drug Metab. Dispos., 32, Ćaleta, I., Kralj, M., Marjanović, M., Bertoša, B., Tomić, S., Pavlović, G., Pavelić, K. & Karminski-Zamola, G. (2009). J. Med. Chem. 52, Higashi, T. (2000). NUMABS. Rigaku Corporation, Tokyo, Japan. Lynch, D. E. (2002). Acta Cryst. E58, o1139 o1141. Matković-Čalogović, D., Popović, Z., Tralić-Kulenović, V., Racanè, L. & Karminski-Zamola, G. (2003). Acta Cryst. C59, o190 o191. McArdle, P. (1995). J. Appl. Cryst. 28, 65. Mortimer, C. G., Wells, G., Crochard, J., Stone, E. L., Bradshaw, T. D., Stevens, M. F. G. & Westwell, A. D. (2006). J. Med. Chem. 49, Palmer, P. J., Trigg, R. B. & Warrington, J. V. (1971). J. Med. Chem. 14, Rigaku (2007). CrystalClear. Rigaku Inc., Tokyo, Japan. Sheldrick, G. M. (2008). Acta Cryst. A64, Spek, A. L. (2009). Acta Cryst. D65, o914 Lei et al. doi: /s x Acta Cryst. (2010). E66, o914
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3 Acta Cryst. (2010). E66, o914 [ doi: /s x ] Ethyl 2-(tert-butoxycarbonylamino)-1,3-benzothiazole-6-carboxylate C. Lei, X. Fang, H.-Y. Yu, M.-D. Huang and J.-D. Wang Comment Benzothiazole is an important moiety used in drug development because of its biological activities. A number of benzothiazole derivatives were shown to have anti-tumor (Brantley et al., 2004; Mortimer et al., 2006; Ćaleta et al., 2009) or anti-microbial activities (Palmer et al., 1971). During our development of 2-aminobenzothiazole-based Urokinase-Type Plasminogen Activator (upa) inhibitors, we synthesized the title compound as an intermediate while its activity was not tested because it is only a fragment of our target molecule. The molecular structure of the compound is shown in Fig. 1. The benzothiazole moiety in this structure is very similar to other benzothiazole compounds reported before (Lynch, 2002; Matković-Čalogović et al., 2003). The dihedral angle between the carbonylamino group and the planar central 9-membered ring system is 7.59 (6), and between the central rings and the ethylcarboxylate group is 7.72 (6), respectively. The packing of molecules is shown in Fig. 2. Molecules form pairs via N H N and C H O hydrogen bonds over crystallographic inversion symmetry. π π stacking and C14 H14A Cg2 hydrogen bonds (Cg2 is the benzene ring centroid) link pairs in a stacking column. In the π π packing, Cg1 Cg1 iii is (2) Å (Cg1 is the thiazole ring centroid and symmetry code iii = -x, 2-y, 2-z), the plane to plane distance of the two thiazole rings is Å with an offset of Å, Cg1 Cg2 iii is (2) Å, the perpendicular distances of Cg1 to benzene ring is Å, and Cg2 to thiazole ring is Å. The hydrogen bonds are listed in Table 1, and the stacking geometries calculated with PLATON (Spek, 2009). Experimental Di-tert-butyl dicarbonate (4.92 g, 22.5 mmol) and 4-dimethylamino pyridine (2.06 g, 16.9 mmol) were added to a solution of ethyl 2-aminebenzothiazole-6-carboxylate (the starting compound) (2.5 g, 11.3 mmol) in dry THF (300 ml), and stirred for 22 hours at room temperature. Then the solvent THF was evaporated, and the residue was extracted with 1 liter of dichloromethane. The dichloromethane washed with 1 N aq HCl, water, and brine, sequentially, and dried with Na 2 SO 4. Further filtration and concentration yielded the dried compound as a yellow solid [2.61 g, yield: 72%]. The solid was dissolved in DMF and filtered. The DMF was evaporated slowly at room temperature for a week, giving colorless needle crystals. Refinement All H atoms bound to C and N atoms were refined as riding, with C H distances in the range of 0.93 to 0.97 Å and N H distances of 0.86 Å, with U iso (H) = 1.2U eq (C, N); 1.5U eq (C methyl ). sup-1
4 Figures Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are shown at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radii. Fig. 2. The packing diagram for the title compound. All hydrogen atoms have been omitted for clarity. Hydrogen bonds are indicated by dashed lines. Ethyl 2-(tert-butoxycarbonylamino)-1,3-benzothiazole-6-carboxylate Crystal data C 15 H 18 N 2 O 4 S Z = 2 M r = F(000) = 340 Triclinic, P1 D x = Mg m 3 Hall symbol: -P 1 Mo Kα radiation, λ = Å a = (13) Å Cell parameters from 2354 reflections b = (2) Å θ = c = (2) Å µ = 0.22 mm 1 α = (3) T = 293 K β = (3) Needle, colorless γ = (3) mm V = (3) Å 3 Data collection Rigaku Saturn 724 CCD area-detector diffractometer Radiation source: fine-focus sealed tube Graphite R int = independent reflections 2412 reflections with I > 2σ(I) Detector resolution: pixels mm -1 θ max = 27.5, θ min = 3.3 dtprofit.ref scans Absorption correction: numerical (NUMABS; Higashi, 2000) T min = 0.987, T max = measured reflections h = 7 8 k = l = sup-2
5 Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained S = 1.11 w = 1/[σ 2 (F 2 o ) + (0.0613P) P] where P = (F 2 o + 2F 2 c )/ reflections (Δ/σ) max < parameters Δρ max = 0.26 e Å 3 0 restraints Δρ min = 0.30 e Å 3 Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wr and goodness of fit S are based on F 2, conventional R-factors R are based on F, with F set to zero for negative F 2. The threshold expression of F 2 > σ(f 2 ) is used only for calculating R- factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq S (16) (10) (9) (3) O (4) (2) (2) (7) N (5) (3) (3) (7) H * O (4) (3) (2) (7) N (5) (3) (2) (7) O (5) (3) (3) (10) O (5) (3) (3) (9) C (11) (5) (5) (2) H1A * H1B * H1C * C (9) (6) (5) (2) H2A * H2B * H2C * C (8) (5) (5) (17) H3A * sup-3
6 H3B * H3C * C (7) (4) (4) (11) C (6) (4) (3) (9) C (6) (4) (3) (8) C (5) (3) (3) (8) C (6) (4) (3) (9) H * C (6) (4) (3) (9) H * C (5) (4) (3) (9) C (6) (4) (3) (9) H * C (6) (3) (3) (8) C (6) (4) (3) (9) C (6) (4) (3) (10) H14A * H14B * C (9) (5) (5) (15) H15A * H15B * H15C * Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 S (6) (6) (6) (4) (4) (5) O (15) (15) (17) (12) (13) (13) N (16) (18) (18) (13) (14) (14) O (14) (18) (17) (13) (12) (14) N (16) (18) (16) (13) (13) (14) O (19) (18) (2) (15) (17) (16) O (18) (2) (2) (15) (16) (17) C (5) (3) (5) (3) (4) (3) C (4) (6) (4) (4) (3) (4) C (3) (3) (4) (2) (3) (3) C (2) (2) (3) (19) (2) (2) C (2) (2) (2) (17) (18) (19) C (18) (2) (19) (15) (15) (16) C (17) (2) (19) (15) (15) (16) C (19) (2) (2) (16) (17) (18) C (2) (2) (2) (17) (18) (19) C (18) (2) (2) (16) (15) (18) C (19) (2) (2) (16) (16) (18) C (19) (2) (19) (16) (15) (16) C (19) (3) (2) (18) (16) (19) C (2) (3) (2) (19) (18) (2) C (3) (3) (4) (3) (3) (3) sup-4
7 Geometric parameters (Å, ) S1 C (4) C3 C (6) S1 C (4) C3 H3A O1 C (4) C3 H3B O1 C (5) C3 H3C N1 C (5) C7 C (5) N1 C (5) C7 C (5) N1 H C8 C (5) O4 C (5) C8 H O4 C (4) C9 C (5) N2 C (4) C9 H N2 C (4) C10 C (5) O2 C (5) C10 C (5) O3 C (4) C11 C (5) C1 C (7) C11 H C1 H1A C14 C (6) C1 H1B C14 H14A C1 H1C C14 H14B C2 C (7) C15 H15A C2 H2A C15 H15B C2 H2B C15 H15C C2 H2C C12 S1 C (18) N2 C6 S (3) C5 O1 C (3) N1 C6 S (3) C5 N1 C (3) N2 C7 C (3) C5 N1 H N2 C7 C (3) C6 N1 H C8 C7 C (3) C13 O4 C (3) C9 C8 C (4) C6 N2 C (3) C9 C8 H C4 C1 H1A C7 C8 H C4 C1 H1B C8 C9 C (4) H1A C1 H1B C8 C9 H C4 C1 H1C C10 C9 H H1A C1 H1C C11 C10 C (3) H1B C1 H1C C11 C10 C (3) C4 C2 H2A C9 C10 C (3) C4 C2 H2B C10 C11 C (4) H2A C2 H2B C10 C11 H C4 C2 H2C C12 C11 H H2A C2 H2C C11 C12 C (3) H2B C2 H2C C11 C12 S (3) C4 C3 H3A C7 C12 S (3) C4 C3 H3B O3 C13 O (4) H3A C3 H3B O3 C13 C (4) C4 C3 H3C O4 C13 C (3) H3A C3 H3C O4 C14 C (3) H3B C3 H3C O4 C14 H14A sup-5
8 O1 C4 C (4) C15 C14 H14A O1 C4 C (4) O4 C14 H14B C2 C4 C (5) C15 C14 H14B O1 C4 C (3) H14A C14 H14B C2 C4 C (5) C14 C15 H15A C1 C4 C (4) C14 C15 H15B O2 C5 O (4) H15A C15 H15B O2 C5 N (3) C14 C15 H15C O1 C5 N (3) H15A C15 H15C N2 C6 N (3) H15B C15 H15C Hydrogen-bond geometry (Å, ) Cg2 is the centroid of the C7 C12 benzene ring. D H A D H H A D A D H A N1 H1 N2 i (14) 162. C8 H8 O1 i (14) 164. C14 H14A Cg2 ii (18) 149. Symmetry codes: (i) x 1, y+2, z+2; (ii) x+1, y, z. sup-6
9 Fig. 1 sup-7
10 Fig. 2 sup-8
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