Supporting Information

Transcription

1 Supporting Information Intermolecular contacts in compressed α-d-mannose Ewa Patyk-Kaźmierczak, a Mark R. Warren, b David R. Allan, b Andrzej Katrusiak a a Department of Materials Chemistry, Faculty of Chemistry, Umultowska 89b, Poznań Poland; b Diamond Light Source, Harwell Science and Innovation Campus, Didcot, Oxon OX11 0DE, UK 1

2 Figure S1. Temperature dependence of unit-cell parameters and volume of α-d-mannose crystals in K range. Figure S2. Pressure dependence of compressibility β calculated for (a) unit-cell volume and parameters as well as for (b) distances between mannose rings centroids (Figure S3, Table S15). Compressibility β calculated for the distances between parallel molecules along directions [100], [010] and [001] is marked with red, green, blue dashed lines, respectively; between molecules A and B in the aggregate (Figure S14) in black, and for molecules of the same type, bonded with the shortest OH O hydrogen bonds, are marked in dark cyan, pink, dark yellow and dark red, according to the description included in the Figure S3. 2

3 Figure S3. Pressure dependence of the distance between centroids calculated for mannose rings. The distance between asymmetric molecules A and B involved in the aggregate (Figure S14), closest parallel molecules of the same type along directions [100],[010] and [001], are marked in black, red, green and blue, respectively. Distances between molecules of the same type, bonded with the shortest OH O hydrogen bonds, are marked in dark cyan, pink, dark yellow and dark red, according to the description included in the Figure S3. Figure S4. Changes of the unit-cell voids volume in the function of pressure, calculated with the Mercury program, 1 for probe radius and grid spacing of 0.4 and 0.1 Å, respectively (solid lines), as well as 0.2 and 0.1 Å (dashed lines). Values in Å 3 and % are marked in black and red, respectively. 3

4 Figure S5. Superposition of molecules A and B with bonds C2-C2-O5 positioned in the same way. Molecule A and B at are marked in green and red, respectively, and at 9.0 in black and blue. In the bottom part of the figure superposition of the same type of the molecule at two extreme pressures of and 9.0 has been included. Figure S6. Pressure dependence of torsion angles C/Ox-Cx-Ox-Hx in α-d-mannose molecule A (solid lines) and B (dashed lines). 4

5 Figure S7. Pressure dependence of torsion angles C4-C5-C6-O6 and O5-C5-C6-O6 in both independent molecules of α-d-mannose. Figure S8. Fisher projection of α-d-mannose with OH O bonds shown from the perspective of the donor OH group, marked with solid and dashed lines for interactions where molecule A and B is a donor, respectively. ORTEP symmetry code 2 is explicitly explained in Table S13. 5

6 Figure S9. The pressure dependence of (a) C-O O, (b) O O-C and (c) O-H O angles for OH O hydrogen bonds in compressed α-d-mannose. Values for H-bonds where mannose molecule A act as a donor are marked with solid lines, and those where molecule B is a donor with dashed lines. Non-bonding O O contacts are marked with dotted lines. ORTEP symmetry code 2 is explicitly explained in Table S13. 6

7 Figure S10. The pressure dependence of (a) C O and (b) H O distances for CH O contacts in compressed α-d-mannose. The sum of van der Waals radii for carbon-oxygen, and oxygenhydrogen atoms, of 3.22 and 2.72 Å, 3 respectively, is marked with horizontal dashed red line. Values for contacts where mannose molecule A act as a donor are marked with solid lines, and those where molecule B is a donor with dashed lines. ORTEP symmetry code 2 is explicitly explained in Table S13. 7

8 Figure S11. The pressure dependence of (a) C O-C and (b) C-H O angles for CH O contacts in compressed α-d-mannose. The limit for C-H O angle 4 equal to 110 is marked with horizontal dashed red line. Values for contacts where mannose molecule A act as a donor are marked with solid lines, and those where molecule B is a donor with dashed lines. ORTEP symmetry code 2 is explicitly explained in Table S13. 8

9 Figure S12. The pressure dependence of H H distances for H H interactions in compressed α-d-mannose. The sum of van der Waals radii for two hydrogen atoms, of 2.4 Å 3 is marked with horizontal dashed red line. ORTEP symmetry code 2 is explicitly explained in Table S13. 9

10 Figure S13. Pressure dependence of distances from the centroids of central molecules A (a) and B (b) to all centroids closer than 12 Å around in α-d-mannose. Distances A A and B B are marked with solid lines, while dashed lines represent distances A B/B A. ORTEP 4-digit codes 2 and symmetry transformations are listed in Supporting Table S13. 10

11 Figure S14. Projection of (a) α-d-mannose molecules A (orange) and B (blue) aggregate shown along direction [001], and (b) packing of aggregates shown along directions [100] and [001] prepared in program Mercury. 1 Each aggregate, consisting of molecule A and B, in figure S14b has been shown in different colour for clarity. 11

12 Tables Table S1. Crystallographic and experimental data for α-d-mannose crystal structures in temperature range K. C 6 H 12 O 6 Phase I Phase I Phase I Phase I Pressure () Temperature (K) 295.1(3) 250.0(1) 200.0(1) 150.1(3) Formula weight Crystal colour Colourless Colourless Colourless Colourless Crystal size (mm) 0.75x0.58x x0.58x x0.58x x0.58x0.10 Crystal system Orthorhombic Orthorhombic Orthorhombic Orthorhombic Space group P P P P Unit cell dimensions (Å) a (3) (4) (4) (5) b (11) (13) (15) (17) c (9) (11) (13) (14) Volume (Å 3 ) (3) (4) (5) (5) Z D x (g cm -3 ) Wavelength λ (Å) Absorption coefficient (mm -1 ) F(000) (e) θ max ( o ) Min./Max. indices h k l -23/29-11/12-8/8-29/23-12/11-8/8-23/29-12/11-8/8-29/23-12/11-8/8 Reflections collected/unique 7503/ / / /3003 R int Observed reflections (I>4σ I ) Data/parameters 2868/ / / /217 Goodness of fit on F Final R 1 indices (I>4σ I ) R 1 /wr 2 indices (all data) / / / / σ max, σ min (eå -3 ) 0.415, , , , Weighting scheme a : x; y ; , , , 0 Extinction coefficient Absorption corrections sample crystal sample crystal sample crystal sample crystal Sample transmission min/max 0.14/ / / / 1.00 a w = 1/(σ2(Fo2)+x2P2+yP), where P=(Max(Fo2, 0)+2Fc2)/3 12

13 Table S2. High-pressure crystallographic and experimental data for α-d-mannose crystal structures in pressure range. Due to the poor quality of data collected at 6.63, 8.01, 9.20, 9.37, 9.54 and inhibiting the structure solution, information included in the table are limited. C 6H 12O 6 Phase I Phase I Phase I Phase I Phase I Phase I Phase I Phase I Phase I Pressure () 0.50(2) 1.00(2) 1.61(2) 2.16(2) 2.49(2) 3.00(2) 3.42(2) 4.00(2) 4.39(2) Temperature (K) 295(2) 295(2) 295(2) 295(2) 295(2) 295(2) 295(2) 295(2) 295(2) Formula weight Crystal colour Colourless Colourless Colourless Colourless Colourless Colourless Colourless Colourless Colourless Crystal size (mm) 0.30x0.20x x0.21x x0.25x x0.25x x0.25x x0.25x x0.25x x0.25x x0.12x0.08 Crystal system Orthorhombic Orthorhombic Orthorhombic Orthorhombic Orthorhombic Orthorhombic Orthorhombic Orthorhombic Orthorhombic Space group P P P P P P P P P Unit cell dimensions (Å; o ) a = (2) 22.93(11) 22.66(2) 22.38(3) 22.17(3) 22.09(2) 21.93(3) 21.90(3) 21.71(5) b = (9) 9.244(5) (9) (9) (14) (11) (14) (11) (17) c = (9) 6.808(6) (8) (8) (11) (8) (11) (9) 6.639(2) Volume (Å 3 ) (13) 1443(7) (14) (16) (19) (14) (19) (16) 1290(3) Z D x (g cm -3 ) Wavelength MoKα, λ (Å) Absorption coefficient (mm -1 ) F(000) (e) θ max ( o ) Min./Max. indices h k l -9/9-11/11-7/8-11/11-15/15-10/10-8/8-11/10-8/8 a w = 1/(σ2(Fo2)+x2P2+yP), where P=(Max(Fo2, 0)+2Fc2)/3-7/7-11/11-8/8 Reflections collected/unique 4566/ / / / / / / / /616 R int Observed reflections (I>4σ(I)) Data/parameters 806/ /80 819/97 838/97 794/97 788/97 774/97 777/97 616/97 Goodness of fit on F Final R 1 indices (I>4σ(I)) R 1/wR 2 indices (all data) / / / / / / / / / σ max, σ min (eå -3 ) 0.244, , , , , , , , , Weighting scheme a : x; y ; ; ; ; ; ; ; ; ; 0 Extinction coefficient Absorption corrections sample crystal sample crystal sample crystal sample crystal sample crystal sample crystal sample crystal Not enough coverage in data - -7/7-11/10-8/8-7/7-11/10-8/8-7/7-11/10-8/8 Sample transmission min/max 0.83/ / / / / / /1.00-7/7-11/10-8/8-8/8-11/11-8/8 absorption correction could not be applied 13

14 Table S2. Continuation. C 6H 12O 6 Phase I Phase I Phase I Phase I Phase I Phase I Phase I Phase I Pressure () 4.71(2) 4.84(2) 5.38(2) 5.55(2) 8.29(2) 8.60(2) 8.77(2) 9.00(2) Temperature (K) 295(2) 295(2) 295(2) 295(2) 295(2) 295(2) 295(2) 295(2) Formula weight Crystal colour Colourless Colourless Colourless Colourless Colourless Colourless Colourless Colourless Crystal size (mm) 0.13x0.12x x0.12x x0.16x x0.16x x0.07x x0.07x x0.07x x0.07x0.05 Crystal system Orthorhombic Orthorhombic Orthorhombic Orthorhombic Orthorhombic Orthorhombic Orthorhombic Orthorhombic Space group P P P P P P P P Unit cell dimensions (Å; o ) a = 21.66(8) 21.64(13) (7) 21.61(2) (13) (16) (14) (19) b = 8.915(2) 8.907(3) (13) 8.864(2) (7) (9) (7) (10) c = 6.625(4) 6.621(6) (5) (13) (5) (6) (5) (6) Volume (Å 3 ) 1279(5) 1276(8) (4) (14) (8) (9) (8) (11) Z D x (g cm -3 ) Wavelength MoKα, λ (Å) Absorption coefficient (mm -1 ) F(000) (e) θ max ( o ) Min./Max. indices h k l -8/8-11/11-7/7-8/8-11/10-7/7-15/15-9/9-8/7 Reflections collected/unique 3715/ / / / / / / /727 R int Observed reflections (I>4σ(I)) Data/parameters 586/95 576/92 782/97 755/97 533/97 778/97 783/97 727/97 Goodness of fit on F Final R 1 indices (I>4σ(I)) R 1/wR 2 indices (all data) / / / / / / / / σ max, σ min (eå -3 ) 0.178, , , , , , and , Weighting scheme a : x; y ; ; ; ; ; ; ; ; Extinction coefficient Absorption corrections Not enough coverage in data - sample crystal sample crystal sample crystal sample crystal sample crystal sample crystal Sample transmission min/max absorption correction could not be 0.92/ / / / / /1.00 applied a w = 1/(σ2(Fo2)+x2P2+yP), where P=(Max(Fo2, 0)+2Fc2)/3-11/11-10/10-8/7-10/11-11/11-7/7-11/11-11/11-7/7-11/10-11/11-7/7-10/11-11/11-7/7 14

15 Table S2. Continuation; limited crystallographic and experimental data for α-d-mannose at 6.63, 8.01, 9.20, 9.37, 9.54 and C 6H 12O 6 Phase I Phase I Phase I Phase I Phase I Phase I Pressure () 6.63(2) 8.01(2) 9.20(2) 9.37(2) 9.54(2) 10.13(2) Temperature (K) 295(2) 295(2) 295(2) 295(2) 295(2) 295(2) Formula weight Crystal colour Colourless Colourless Colourless Colourless Colourless Colourless Crystal size (mm) 0.09x0.07x x0.07x x0.07x x0.07x x0.07x x0.07x0.05 Crystal system Orthorhombic Orthorhombic Orthorhombic Orthorhombic Orthorhombic Orthorhombic Space group P P P P P P Unit cell dimensions (Å; o ) a = 21.31(3) 21.08(3) (9) (14) (12) (12) b = (17) (9) (5) (8) (7) (7) c = (16) (8) (3) (6) (5) (5) Volume (Å 3 ) (19) (15) (5) (8) (7) (7) Z D x (g cm -3 ) Wavelength MoKα, λ (Å) Absorption coefficient (mm -1 ) F(000) (e) θ max ( o ) Min./Max. indices h k l -9/9-7/7-5/5-7/7-7/7-5/5 Reflections collected/unique 1122/ / / / / /359 R int Observed reflections (I>4σ(I)) σ max, σ min (eå -3 ) 2.098, , , , , , Absorption corrections sample crystal sample crystal sample crystal sample crystal sample crystal sample crystal Sample transmission min/max 0.29/ / / / / /1.00-9/10-7/7-5/5-9/9-7/7-5/5-10/9-7/7-5/5-9/9-7/7-5/5 Table S3. Double exponential decay functions fitted to the experimentally obtained pressure dependences of unit-cell volume V and parameters a, b, c of α-d-mannose used for the calculation of the differential part of compressibility parameter = coefficient. Function a(p) a = *exp( *p) *exp( *p) (R= ) b(p) b = *exp( *p) *exp( *p) (R= ) c(p) c = *exp( *p) *exp(-4.409*10-13 *p) (R= ) V(p) V = *exp( *p) *exp( *p) (R= ). R is correlation 15

16 Table S4. Double exponential decay functions fitted to the experimentally obtained pressure dependences of distance between centroids calculated for mannose rings (Table S15): between asymmetric molecules A and B involved in the same aggregate (Mol. A Mol. B), closest parallel molecules of the same type along directions [100], [010] and [001] (Mol. Mol. along x, y, z); between molecules of the same type, bonded with the shortest OH O hydrogen bonds (Mol. A Mol. A and Mol. B Mol. B, symmetry joining two molecules is described with 4-digit ORTEP code 2 explained in Table S13). Those functions were used for the calculation of the differential part of compressibility parameter =. R is correlation coefficient. Mol. A Mol. B (p) Mol. Mol. along x (p) Mol. Mol. along y (p) Mol. Mol. along z (p) Mol. A Mol. A 3556 (p) Mol. A Mol. A 2564 (p) Mol. B Mol. B 2575 (p) Mol. B Mol. B 1554 (p) Function f = *exp( *p) *exp( *10-13 *p) (R= ) f = *exp( *p) *exp( *10-11 *p) (R= ) f = *exp( *p) *exp( *p) (R= ) f = *exp( *p) *exp( *10-13 *p) (R= ) f = *exp( *p) *exp( *p) (R= ) f = *exp( *p) *exp( *10-12 *p) (R= ) f = *exp( *p) *exp( *10-11 *p) (R= ) f = *exp( *p) *exp( *10-13 *p) (R= ) 16

17 Table S5. Compressibility =, where x stands for unit-cell parameters a, b, c and volume V, in α-d-mannose. The differential part was analytically calculated based on an double exponential decay function fitted to the experimentally obtained pressure dependences of unit-cell volume V and parameters a, b, c. Used functions are listed in Table S3. Pressure β V [ -1 ] β a [ -1 ] β b [ -1 ] β c [ -1 ] 0.10 MPa 6.25* * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * *

18 Table S6. Compressibility =, where x stands for distance between centroids calculated for mannose rings in α-d-mannose, as described in the heading of Table S4. The differential part was analytically calculated based on an exponential decay function fitted to the experimentally obtained pressure dependences of distance between centroids (Table S15). Used functions are listed in Table S4. Symmetry ORTEP codes 2 are explicitly explained in Table S13. β[ -1 ] Mol. A Mol. A/ Mol. B Mol. B Mol. A Mol. A Mol. B Mol. B Mol. A Mol. B pressure Along x Along y Along z MPa 7.85* * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * * *

19 Table S7. Structural voids volume in α-d-mannose crystals calculated with program Mercury 1 for probe radius of 0.4 or 0.2 Å and grid spacing of 0.1 Å. Pressure Probe radius:0.4å; Grid Spacing:0.1Å Probe radius:0.2å; Grid Spacing:0.1Å % Å 3 % Å MPa Table S8. Torsion angles C4-C5-C6-O6 and O5-C5-C6-O6 in both independent molecules of α-d-mannose. Torsion Angle Pressure Molecule A 19 Molecule B C4-C5-C6-O6 O5-C5-C6-O6 C4 -C5 -C6 -O6 O5 -C5 -C6 -O MPa 58.2(10) -64.2(8) (6) 66.1(9) (25) -64.1(14) (15) 60.8(26) (18) -59.8(12) (13) 64.6(23) (34) -64.3(18) (19) 64.1(33) (23) -62.5(12) (13) 67.7(25) (23) -61.8(11) (14) 65.6(25) (23) -60.9(12) (14) 67.1(25) (22) -61.3(12) (13) 67.8(23) (24) -61.7(14) (15) 65.3(27) (14) -60.7(10) (13) 64.5(15) (17) -60.2(11) (13) 67.6(20) (22) -58.3(15) (16) 66.5(26) (16) -58.9(10) (12) 65.9(19) (16) -59.4(10) (11) 66.2(17) (16) -57.8(10) (11) 66.5(18)

20 Table S9. Torsion angles O/C-C-O-H of hydroxyl groups in both independent molecules of α-d-mannose. Pressure Torsion Angle Molecule A O5-C1-O1-H8 C1-C2-O2-H9 C2-C3-O3-H10 C3-C4-O4-H11 C5-C6-O6-H MPa Torsion Angle Molecule B Pressure O5 -C1 -O1 -H8 C1 -C2 -O2 -H9 C2 -C3 -O3 -H10 C3 -C4 -O4 -H11 C5 -C6 -O6 -H MPa

21 O1 H8 O6 (2575) O6H12 O4 (1556) O4H11 O6(2564) O3H10 O4 (1555) O2H9 O1(3556) O1H8 O5 (1546) O1H8 O2 (1546) Table S10. Geometry of OH O hydrogen bonds in α-d-mannose. Symmetry ORTEP codes 2 are explicitly explained in Table S MPa O O 2.846(8) 2.84(11) 2.859(12) 2.869(13) 2.878(10) 2.882(10) 2.895(11) 2.915(10) 2.927(11) H O O-H O C-O O 100.6(4) 98.6(6) 96.5(6) 95.7(7) 92.7(6) 91.7(6) 91.0(6) 90.2(6) 88.9(7) O O-C 127.6(5) 126.2(14) 123.0(13) 126.5(17) 120.9(13) 121.1(13) 119.5(13) 118.6(12) 118.4(13) O O 3.135(7) 3.019(21) 2.931(25) 2.941(30) 2.841(24) 2.791(23) 2.786(24) 2.740(22) 2.723(25) H O O-H O C-O O 104.7(4) 106.1(15) 106.0(14) 106.1(21) 103.3(17) 103.8(17) 103.2(17) 103.6(15) 103.4(18) O O-C O O 2.775(8) 2.745(27) 2.711(29) 2.680(38) 2.658(28) 2.657(29) 2.660(29) 2.664(27) 2.663(31) H O O-H O C-O O 105.7(4) 105.6(13) 106.9(14) 105.6(17) 104.9(13) 104.8(13) 105.0(13) 104.2(12) 103.9(15) O O-C 125.4(2) 122.3(17) 121.4(17) 121.1(24) 122.3(20) 120.4(20) 120.9(20) 120.0(18) 119.2(22) O O 2.897(7) 2.810(16) 2.783(19) 2.773(21) 2.731(17) 2.722(16) 2.697(17) 2.687(15) 2.700(17) H O O-H O C-O O 136.8(5) 137.5(15) 136.8(16) 138.0(25) 138.2(19) 136.1(18) 137.1(18) 135.2(17) 132.1(19) O O-C 115.3(4) 116.5(9) 116.7(10) 116.6(13) 117.2(10) 117.5(10) 118.6(10) 117.9(10) 116.7(11) O O 2.761(8) 2.778(27) 2.757(26) 2.722(40) 2.668(29) 2.691(29) 2.651(29) 2.625(27) 2.634(32) H O O-H O C-O O 112.7(4) 112.0(11) 110.4(10) 112.3(15) 110.7(12) 109.8(11) 108.4(12) 108.6(11) 108.2(13) O O-C 123.3(5) 120.0(17) 119.9(15) 118.4(25) 115.6(20) 113.9(19) 113.0(19) 113.8(18) 114.1(20) O O 2.896(8) 2.863(24) 2.851(28) 2.813(34) 2.805(27) 2.779(26) 2.777(26) 2.765(24) 2.759(28) H O O-H O C-O O 117.5(5) 120.2(16) 119.9(14) 120.5(22) 121.6(18) 122.5(17) 123.0(18) 122.3(16) 121.2(19) O O-C 123.3(5) 121.9(12) 119.5(14) 118.7(17) 115.8(13) 114.3(14) 113.6(14) 113.9(13) 114.2(15) O O 2.636(8) 2.645(25) 2.657(26) 2.623(37) 2.575(27) 2.590(25) 2.593(27) 2.575(25) 2.563(28) H O O-H O C-O O 106.2(4) 105.9(9) 103.1(9) 105.2(11) 103.5(10) 102.1(10) 102.6(10) 100.3(10) 101.0(11) O O-C 133.9(5) 133.9(9) 133.6(8) 134.8(10) 133.6(8) 133.3(8) 132.6(8) 132.5(7) 131.9(9) intermolecular contact between two molecules of the same type (A-A or B-B) intermolecular contact between two molecules of different types (A-B or B-A) 21

22 Table S10. Continuation. O6 H12 O1 (1554) O4 H11 O5(1554) O4 H11 O2(1554) O3 H10 O2(1555) O3 H10 O3(1555) O2 H9 O3(3555) O1 H8 O5 (2575) 0.10 MPa O O 3.592(8) 3.542(26) 3.480(30) 3.420(37) 3.375(28) 3.338(27) 3.313(28) 3.286(27) 3.255(29) H O O-H O C-O O 155.9(4) 155.2(9) 152.3(9) 154.2(11) 153.3(9) 152.2(9) 152.4(9) 151.3(9) 151.9(10) O O-C O O 2.929(8) 2.910(30) 2.890(32) 2.904(40) 2.818(30) 2.828(29) 2.831(30) 2.819(27) 2.806(30) H O O-H O C-O O 105.6(4) 105.2(3) 102.5(3) 99.2(5) 97.3(4) 96.9(4) 95.5(4) 93.5(3) 92.7(4) O O-C 51.4(1) 51.8(3) 52.1(3) 51.5(5) 51.2(4) 51.8(4) 52.2(4) 52.6(3) 52.9(4) O O 2.890(7) 2.880(11) 2.847(13) 2.851(14) 2.850(10) 2.829(10) 2.837(10) 2.832(10) 2.819(11) H O O-H O C-O O 103.3(4) 102.5(10) 103.3(11) 105.2(14) 104.8(11) 104.5(10) 104.2(10) 104.0(10) 104.9(11) O O-C 129.4(5) 127.5(7) 126.9(7) 125.4(9) 123.0(7) 122.8(7) 121.3(7) 120.0(6) 119.5(8) O O 3.496(8) 3.431(10) 3.379(12) 3.348(14) 3.28(10) 3.243(10) 3.211(10) 3.191(10) 3.154(12) H O O-H O C-O O 121.9(5) 122.9(13) 125.7(13) 128.2(19) 129.6(14) 128.6(14) 129.7(15) 131.0(14) 131.9(16) O O-C 109.2(4) 109.8(6) 109.9(5) 111.1(7) 112.4(6) 113.1(5) 113.2(6) 113.2(5) 114.6(6) O O 2.779(8) 2.785(18) 2.777(21) 2.754(24) 2.720(18) 2.693(18) 2.679(18) 2.665(17) 2.666(20) H O O-H O C-O O 102.7(4) 102.9(10) 103.7(11) 105.2(14) 105.7(11) 106.6(10) 106.1(11) 106.0(10) 106.6(12) O O-C 122.6(4) 121.8(11) 119.7(12) 121.2(14) 120.7(11) 119.7(11) 119.7(12) 120.3(11) 120.0(12) O O 2.936(6) 2.931(11) 2.924(13) 2.909(13) 2.865(11) 2.872(10) 2.865(11) 2.862(10) 2.853(12) H O O-H O C-O O 160.3(5) 159.7(8) 160.7(8) 161.7(8) 161.5(6) 161.7(6) 160.8(7) 161.2(6) 162.1(7) O O-C O O 2.686(8) 2.655(13) 2.658(12) 2.655(14) 2.61(11) 2.606(11) 2.597(12) 2.577(11) 2.559(13) H O O-H O C-O O 115.7(5) 117.0(14) 118.7(14) 117.7(21) 118.9(15) 120.0(15) 120.2(15) 119.2(14) 120.4(17) O O-C 133.6(5) 131.3(13) 129.6(13) 127.1(18) 126.5(15) 127.0(15) 125.6(15) 127.2(14) 125.5(16) intermolecular contact between two molecules of the same type (A-A or B-B) intermolecular contact between two molecules of different types (A-B or B-A) 22

23 Table S10. Continuation. O1 H8 O6 (2575) O6H12 O4 (1556) O4H11 O6(2564) O3H10 O4 (1555) O2H9 O1(3556) O1H8 O5 (1546) O1H8 O2 (1546) O O 2.957(16) 2.939(20) 2.972(23) 2.918(10) 2.923(11) 2.942(13) 2.947(11) 2.964(10) 2.947(10) H O O-H O C-O O 89.7(10) 89.9(12) 88.3(13) 88.1(6) 87.2(6) 86.5(7) 85.7(6) 85.3(5) 85.1(5) O O-C 116.6(18) 116.4(30) 117.3(35) 116.7(8) 117.2(10) 112.6(14) 113.2(11) 113.5(10) 111.7(10) O O 2.715(32) 2.692(38) 2.744(45) 2.691(14) 2.708(17) 2.621(27) 2.616(20) 2.613(18) 2.606(19) H O O-H O C-O O 96.5(21) 96.6(28) 97.7(26) 101.3(8) 101.0(11) 99.7(15) 100.4(11) 99.8(10) 99.6(10) O O-C O O 2.626(41) 2.645(50) 2.566(57) 2.637(15) 2.603(21) 2.582(28) 2.572(21) 2.556(20) 2.554(20) H O O-H O C-O O 104.4(22) 103.5(23) 104.0(25) 101.7(7) 103.1(10) 100.6(13) 100.1(10) 99.6(9) 100.2(9) O O-C 126.7(26) 126.3(32) 124.2(32) 120.6(9) 120.9(13) 120.6(18) 120.1(13) 120.4(12) 120.6(12) O O 2.633(20) 2.656(24) 2.613(29) 2.675(11) 2.652(12) 2.621(18) 2.594(14) 2.600(13) 2.579(13) H O O-H O C-O O 136.1(22) 132.5(24) 134.0(28) 134.5(9) 133.8(12) 132.2(20) 133.0(15) 132.8(14) 133.5(14) O O-C 119.6(13) 117.2(16) 122.3(19) 116.3(6) 116.9(7) 116.4(12) 118.3(9) 118.1(8) 118.8(8) O O 2.649(44) 2.665(51) 2.496(54) 2.617(16) 2.620(21) 2.510(31) 2.532(23) 2.537(22) 2.532(23) H O O-H O C-O O 104.5(18) 106.9(20) 107.4(19) 107.0(8) 106.2(9) 106.6(11) 106.1(9) 105.5(9) 105.9(9) O O-C 112.0(23) 113.8(30) 120.2(27) 115.4(9) 112.7(12) 110.6(17) 110.2(13) 109.9(12) 108.7(12) O O 2.787(37) 2.751(43) 2.894(52) 2.715(14) 2.726(18) 2.644(28) 2.682(21) 2.671(19) 2.675(20) H O O-H O C-O O 121.6(21) 119.6(28) 113.5(25) 119.3(7) 120.7(11) 122.8(15) 122.6(12) 122.7(11) 123.4(11) O O-C 110.1(18) 112.6(24) 102.8(29) 114.2(7) 113.3(9) 114.5(15) 112.1(11) 112.1(10) 110.6(10) O O 2.550(38) 2.534(46) 2.543(52) 2.525(16) 2.542(21) 2.449(28) 2.475(20) 2.461(19) 2.472(19) H O O-H O C-O O 100.2(15) 102.2(22) 99.1(27) 99.1(8) 98.9(10) 99.6(12) 99.9(9) 99.7(8) 100.4(8) O O-C 132.0(13) 130.9(14) 130.3(16) 131.4(6) 131.8(7) 130.4(9) 129.6(7) 129.5(6) 129.9(6) intermolecular contact between two molecules of the same type (A-A or B-B) intermolecular contact between two molecules of different types (A-B or B-A) 23

24 Table S10. Continuation. O6 H12 O1 (1554) O4 H11 O5(1554) O4 H11 O2(1554) O3 H10 O2(1555) O3 H10 O3(1555) O2 H9 O3(3555) O1 H8 O5 (2575) O O 3.243(43) 3.147(50) 3.144(59) 3.167(15) 3.217(20) 3.069(31) 3.064(23) 3.038(22) 3.036(22) H O O-H O C-O O 152.8(14) 154.4(19) 152.2(24) 150.7(8) 149.8(10) 151.7(10) 151.9(8) 152.1(7) 152.2(7) O O-C O O 2.711(41) 2.702(50) 2.713(61) 2.760(14) 2.747(20) 2.683(26) 2.667(21) 2.665(20) 2.643(20) H O O-H O C-O O 92.9(5) 90.8(6) 87.5(6) 91.3(2) 91.3(3) 89.2(4) 89.4(3) 87.8(3) 88.2(3) O O-C 52.7(5) 53.1(6) 52.8(6) 52.2(2) 52.4(3) 52.6(4) 52.5(3) 52.5(3) 52.3(3) O O 2.818(15) 2.824(17) 2.821(21) 2.807(11) 2.801(10) 2.807(11) 2.782(8) 2.779(8) 2.783(8) H O O-H O C-O O 103.0(13) 104.3(15) 105.7(18) 105.4(7) 105.7(9) 105.7(12) 105.7(8) 106.4(8) 105.9(8) O O-C 118.4(9) 117.5(11) 116.7(14) 118.5(7) 118.2(6) 114.4(8) 114.5(6) 114.2(6) 114.1(6) O O 3.133(16) 3.121(17) 3.130(22) 3.094(10) 3.094(10) 3.02(13) 3.007(10) 2.987(9) 2.987(9) H O O-H O C-O O 130.0(21) 132.8(24) 139.0(30) 133.0(10) 133.7(13) 134.6(18) 134.1(13) 136.3(13) 135.9(13) O O-C 114.0(8) 112.8(10) 111.3(11) 113.8(5) 113.6(5) 113.8(7) 113.8(5) 114.6(5) 114.2(4) O O 2.600(27) 2.572(32) 2.567(37) 2.607(11) 2.606(13) 2.588(20) 2.578(16) 2.581(14) 2.567(14) H O O-H O C-O O 108.1(14) 107.4(18) 111.1(21) 106.3(7) 105.9(8) 103.2(13) 104.5(9) 104.3(9) 105.5(8) O O-C 120.0(17) 120.7(19) 120.5(21) 121.2(7) 119.9(9) 120.4(11) 121.0(9) 120.9(8) 120.5(8) O O 2.807(16) 2.808(20) 2.812(21) 2.798(10) 2.813(10) 2.794(12) 2.814(9) 2.813(9) 2.798(9) H O O-H O C-O O 160.1(11) 162.1(13) 156.9(23) 162.9(6) 162.2(6) 161.0(7) 160.4(6) 160.5(5) 160.3(6) O O-C O O 2.544(19) 2.547(21) 2.541(24) 2.531(11) 2.541(11) 2.500(14) 2.512(10) 2.517(10) 2.516(10) H O O-H O C-O O 117.7(24) 121.0(28) 121.7(30) 119.9(9) 117.4(12) 119.5(16) 121.1(11) 120.7(11) 121.6(11) O O-C 128.5(24) 122.7(32) 125.7(39) 124.9(8) 126.6(13) 121.3(17) 121.9(13) 121.4(12) 120.5(12) intermolecular contact between two molecules of the same type (A-A or B-B) intermolecular contact between two molecules of different types (A-B or B-A) 24

25 Table S10. Continuation MPa O1 O3 (3546)/ O3 O1(3556) O4 O6 (2565)/ O6 O4(2564) O5 O5 (1546)/ O5 O5(1564) O1 O3 (3546)/ O3 O1(3556) O4 O6 (2565)/ O6 O4(2564) O5 O5 (1546)/ O5 O5(1564) O O 3.350(8) 3.309(23) 3.261(27) 3.195(31) 3.166(25) 3.131(24) 3.108(25) 3.093(24) 3.111(28) C-O O O O-C 70.5(4)/ 165.8(5) 165.8(5)/ 70.5(4) 67.8(14)/ 168.2(11) 168.2(11)/ 67.8(14)/ 66.8(13)/ 171.8(10) 171.8(10)/ 66.8(13)/ 65.8(20)/ 174.1(13) 174.1(13)/ 65.8(20) 66.5(17)/ 178.1(13) 178.1(13)/ 66.5(17) 65.2(17)/ 177.7(13) 177.7(13)/ 65.2(17) 65.7(18)/ 179.4(12) 179.4(12)/ 65.7(18) 64.8(16)/ 177.8(9) 177.8(9)/ 64.8(16) 64.2(19)/ 176.8(12) 176.8(12)/ 64.2(19) O O 3.792(9) 3.701(22) 3.589(24) 3.537(33) 3.426(23) 3.426(23) 3.365(24) 3.314(23) 3.316(27) C-O O O O-C 149.4(4)/ 100.7(5) 100.7(5)/ 149.4(4) 150.4(9)/ 101.5(11) 101.5(11)/ 150.4(9) 150.8(9)/ 103.0(10) 103.0(10)/ 150.8(9) 151.3(12)/ 104.3(15) 104.3(15)/ 151.3(12) 151.1(9)/ 103.0(11) 151.1(9)/ 103.0(11) 150.4(9)/ 103.8(11) 103.8(11)/ 150.4(9) 150.2(10)/ 103.9(11) 103.9(11)/ 150.2(10) 150.9(9)/ 104.4(11) 104.4(11)/ 150.9(9) 149.9(11)/ 104.3(12) 104.3(12)/ 149.9(11) O O 3.314(6) 3.250(11) 3.153(13) 3.132(15) 3.090(11) 3.042(11) 3.039(11) 3.011(10) 2.996(12) C-O O O O-C 88.9/ / / / / / / / / / / / / / / / / / O O 3.026(38) 3.081(43) 3.117(56) 3.046(15) 3.049(20) 2.956(30) 2.929(22) 2.945(21) 2.936(21) C-O O O O-C 70.8(23)/ 176.9(11) 176.9(11)/ 70.8(23) 71.7(29)/ 174.4(19) 174.4(19)/ 71.7(29) 68.6(29)/ 170.0(26) 170.0(26)/ 68.6(29) 65.9(8)/ 175.3(8) 175.3(8)/ 65.9(8) 65.5(11)/ 175.1(10) 175.1(10)/ 65.5(11) 65.9(16)/ 172.8(14) 172.8(14)/ 65.9(16) 65.1(12)/ 173.5(11) 173.5(11)/ 65.1(12) 65.5(11)/ 171.7(11) 171.7(11)/ 65.5(11) 65.5(11)/ 171.7(11) 171.7(11)/ 65.5(11) O O 3.263(37) 3.264(45) 3.232(48) 3.217(14) 3.197(18) 3.028(30) 3.077(21) 3.054(20) 3.059(21) C-O O O O-C 148.4(16)/ 105.1(16) 105.1(16)/ 148.4(16) 149.5(17)/ 106.3(19) 106.3(19)/ 149.5(17) 151.4(18)/ 105.3(21) 105.3(21)/ 151.4(18) 151.2(7)/ 105.0(9) 105.0(9)/ 151.2(7) 149.5(8)/ 106.7(10) 106.7(10)/ 149.5(8) 150.2(10)/ 104.5(12) 104.5(12)/ 150.2(10) 149.6(8)/ 105.0(9) 105.0(9)/ 149.6(8) 149.3(8)/ 105.7(8) 105.7(8)/ 149.3(8) 149.6(8)/ 105.4(8) 105.4(8)/ 149.6(8) O O 2.999(15) 2.994(20) 2.977(19) 2.961(11) 2.949(11) 2.890(13) 2.879(10) 2.875(9) 2.877(9) C-O O O O-C 86.3/ / / / / / / / / / / / / / / / / / 89.9 Non-bonding O O interaction 25

26 Table S11. Geometry of CH O contacts in α-d-mannose. Symmetry ORTEP codes 2 are explicitly explained in Table S13. C1H1 O3(1556) 0.10 MPa C O 3.766(10) 3.719(15) 3.687(14) 3.694(19) 3.637(16) 3.632(15) 3.621(16) 3.611(15) 3.608(17) H O C-H O C O-C 117.7(4) 117.3(6) 116.0(7) 116.8(9) 116.0(7) 115.4(7) 116.4(7) 116.2(7) 114.6(9) C5H5 O5 (1546) C5H5 O1 (2565) C3H3 O2 (1545) C2H2 O2(3546) C1H1 O3 (3546) C1H1 O2 (1546) C O 3.404(9) 3.350(14) 3.323(15) 3.307(17) 3.257(15) 3.251(14) 3.240(15) 3.240(14) 3.218(16) H O C-H O C O-C 124.1(4) 124.4(14) 123.2(14) 127.1(19) 122.2(15) 123.5(15) 122.2(15) 121.9(14) 122.1(16) C O 3.174(10) 3.067(40) 2.999(37) 2.915(53) 2.907(44) 2.845(44) 2.835(45) 2.800(42) 2.802(48) H O C-H O C O-C 152.7(4) 154.2(7) 154.5(8) 153.3(11) 154.8(10) 154.4(10) 153.8(10) 153.1(10) 152.7(12) C O 3.997(9) 3.896(23) 3.817(23) 3.796(32) 3.721(24) 3.693(24) 3.690(24) 3.655(23) 3.625(26) H O C-H O C O-C 141.3(4) 142.4(11) 144.3(12) 142.9(15) 143.6(11) 143.7(11) 144.0(11) 143.4(11) 143.6(12) C O 4.011(9) 3.889(16) 3.753(15) 3.690(20) 3.554(14) 3.507(15) 3.493(15) 3.469(14) 3.431(17) H O C-H O C O-C 81.8(4) 81.1(8) 83.1(7) 84.6(10) 86.2(8) 86.2(8) 86.5(8) 86.4(8) 86.0(9) C O 4.291(10) 4.119(31) 3.953(32) 3.844(43) 3.781(35) 3.702(33) 3.651(34) 3.607(32) 3.594(38) H O C-H O C O-C 137.1(5) 137.9(8) 140.5(7) 139.4(8) 140.3(7) 139.3(7) 139.7(7) 138.2(7) 138.6(8) C O 3.427(8) 3.391(15) 3.303(14) 3.352(18) 3.329(14) 3.319(14) 3.329(15) 3.328(15) 3.307(16) H O C-H O C O-C intermolecular contact between two molecules of the same type (A-A or B-B) intermolecular contact between two molecules of different types (A-B or B-A) 26

27 Table S11. Continuation. C6H6 O6 (2566) 0.10 MPa C O 3.542(11) 3.444(22) 3.405(20) 3.375(31) 3.294(25) 3.283(23) 3.265(25) 3.259(22) 3.249(26) H O C-H O C O-C 116.1(5) 115.6(9) 116.7(8) 115.7(11) 114.1(9) 114.1(8) 114.8(9) 114.5(8) 114.8(10) C4 H4 O3(3555) C3 H3 O6 (1556) C2 H2 O1(1565) C1 H1 O5(1564) C1 H1 O4(1565) C6H7 O6(2564) C O 3.708(11) 3.684(21) 3.590(18) 3.608(25) 3.517(20) 3.472(18) 3.438(19) 3.421(17) 3.417(20) H O C-H O C O-C 129.5(5) 127.3(9) 128.9(8) 125.2(12) 124.3(10) 124.6(9) 124.4(10) 125.1(9) 125.2(10) C O 3.440(9) 3.343(16) 3.197(15) 3.222(18) 3.149(14) 3.107(13) 3.109(14) 3.091(13) 3.081(16) H O C-H O C O-C 116.4(4) 115.4(11) 116.3(10) 113.7(15) 114.1(11) 115.1(11) 114.7(11) 114.8(10) 114.3(12) C O 3.529(9) 3.429(16) 3.378(17) 3.354(20) 3.340(15) 3.311(15) 3.286(15) 3.282(15) 3.283(17) H O C-H O C O-C C O 4.089(10) 3.964(16) 3.923(16) 3.848(18) 3.770(15) 3.721(15) 3.686(15) 3.656(15) 3.596(16) H O C-H O C O-C 125.8(5) 126.4(9) 126.5(8) 126.4(11) 125.5(10) 125.5(9) 125.7(10) 126.1(9) 127.0(10) C O 3.810(10) 3.666(29) 3.622(27) 3.605(38) 3.530(29) 3.463(27) 3.456(29) 3.469(27) 3.431(31) H O C-H O C O-C 70.5(4) 71.2(11) 71.2(11) 69.4(15) 69.2(11) 70.1(10) 69.9(11) 69.0(10) 69.6(12) C O 4.465(10) 4.384(31) 4.306(36) 4.245(45) 4.075(35) 4.041(34) 4.003(35) 3.939(33) 3.898(37) H O C-H O C O-C 90.6(4) 90.7(12) 91.5(11) 91.0(20) 90.9(15) 93.3(14) 93.7(14) 95.6(13) 98.1(15) intermolecular contact between two molecules of the same type (A-A or B-B) intermolecular contact between two molecules of different types (A-B or B-A) 27

28 Table S11. Continuation. C5 H5 O4(2564) 0.10 MPa C O 4.245(10) 4.251(37) 4.107(36) 4.080(52) 3.911(36) 3.947(36) 3.871(36) 3.830(34) 3.865(39) H O C-H O C O-C 121.3(4) 121.4(12) 120.4(11) 121.1(20) 119.3(15) 118.4(14) 117.3(14) 117.9(13) 117.0(15) C6 H7 O3 (1554) C6 H7 O1(1564) C6 H6 O6(1554) C6 H6 O2(1554) C5 H5 O6(1554) C O 3.651(9) 3.600(18) 3.481(19) 3.474(24) 3.348(19) 3.332(19) 3.288(19) 3.264(18) 3.252(20) H O C-H O C O-C 153.7(5) 156.5(17) 156.7(15) 159.4(24) 163.2(20) 163.4(19) 164.6(20) 163.7(18) 162.5(21) C O 3.829(10) 3.758(27) 3.756(28) 3.716(36) 3.703(27) 3.652(28) 3.654(28) 3.636(27) 3.654(30) H O C-H O C O-C 135.7(5) 134.6(13) 131.1(15) 134.1(18) 133.4(14) 133.6(14) 133.0(15) 133.6(13) 134.4(16) C O 3.584(10) 3.500(20) 3.399(19) 3.391(27) 3.280(21) 3.253(21) 3.221(21) 3.210(20) 3.190(22) H O C-H O C O-C 139.3(5) 141.7(13) 139.7(10) 142.6(16) 143.4(12) 142.8(12) 142.8(12) 141.8(11) 141.4(13) C O 3.973(10) 3.835(23) 3.786(25) 3.702(32) 3.609(25) 3.542(24) 3.510(25) 3.463(24) 3.435(27) H O C-H O C O-C 133.8(5) 137.5(17) 138.5(17) 139.3(25) 137.7(20) 139.4(20) 138.9(21) 140.1(19) 140.5(22) C O 3.836(11) 3.691(27) 3.617(28) 3.505(37) 3.401(28) 3.371(28) 3.344(29) 3.295(27) 3.274(32) H O C-H O C O-C 69.5(4) 70.2(10) 71.3(11) 73.3(15) 74.3(12) 73.6(11) 74.1(12) 75.5(11) 75.4(13) intermolecular contact between two molecules of the same type (A-A or B-B) intermolecular contact between two molecules of different types (A-B or B-A) 28

29 Table S11. Continuation. C1H1 O3(1556) C O 3.584(23) 3.585(28) 3.593(29) 3.548(14) 3.528(14) 3.441(16) 3.417(13) 3.433(12) 3.403(11) H O C-H O C O-C 114.8(11) 113.1(13) 114.0(14) 114.8(6) 114.5(6) 116.1(9) 116.2(7) 115.7(6) 115.7(6) C5H5 O5 (1546) C5H5 O1 (2565) C3H3 O2 (1545) C2H2 O2(3546) C1H1 O3 (3546) C1H1 O2 (1546) C O 3.275(24) 3.273(31) 3.249(32) 3.187(15) 3.174(15) 3.186(17) 3.176(13) 3.177(12) 3.159(12) H O C-H O C O-C 116.5(19) 116.5(34) 118.4(37) 120.8(9) 121.4(13) 116.9(16) 118.3(13) 118.5(13) 116.4(12) C O 2.889(61) 2.964(78) 2.914(74) 2.785(21) 2.778(30) 2.706(42) 2.663(34) 2.686(30) 2.68(31) H O C-H O C O-C 153.3(16) 151.5(19) 148.7(24) 151.0(9) 151.0(11) 148.3(15) 148.0(11) 146.7(10) 146.9(10) C O 3.589(36) 3.586(38) 3.539(46) 3.562(16) 3.550(20) 3.495(26) 3.485(19) 3.450(18) 3.456(17) H O C-H O C O-C 144.0(18) 143.9(20) 144.3(21) 142.2(6) 143.4(8) 142.3(11) 142.1(9) 142.1(8) 142.5(8) C O 3.414(24) 3.399(29) 3.392(33) 3.318(15) 3.307(14) 3.236(21) 3.224(13) 3.217(12) 3.200(13) H O C-H O C O-C 84.5(12) 84.5(15) 84.9(16) 87.9(7) 87.9(8) 87.4(10) 88.0(7) 88.0(7) 87.3(7) C O 3.587(42) 3.503(63) 3.521(54) 3.441(19) 3.454(25) 3.269(34) 3.305(24) 3.289(24) 3.260(23) H O C-H O C O-C 136.7(12) 136.7(14) 135.7(17) 139.0(6) 139.9(7) 139.1(8) 138.6(6) 138.6(6) 138.5(6) C O 3.277(21) 3.283(24) 3.270(26) 3.247(15) 3.275(15) 3.257(16) 3.249(11) 3.246(11) 3.243(11) H O C-H O C O-C intermolecular contact between two molecules of the same type (A-A or B-B) intermolecular contact between two molecules of different types (A-B or B-A) 29

30 Table S11. Continuation. C6H6 O6 (2566) C O 3.202(31) 3.289(41) 3.276(38) 3.201(16) 3.178(19) 3.138(24) 3.135(17) 3.134(16) 3.139(15) H O C-H O C O-C 114.2(12) 116.9(15) 117.6(15) 114.9(7) 115.1(7) 111.9(9) 113.0(6) 113.0(6) 112.8(6) C4 H4 O3(3555) C3 H3 O6 (1556) C2 H2 O1(1565) C1 H1 O5(1564) C1 H1 O4(1565) C6H7 O6(2564) C O 3.402(27) 3.399(37) 3.348(33) 3.401(15) 3.359(17) 3.276(23) 3.253(16) 3.264(15) 3.245(15) H O C-H O C O-C 124.3(14) 125.3(17) 128.0(16) 124.9(6) 124.7(8) 123.2(10) 123.4(8) 122.7(8) 122.5(8) C O 3.088(20) 3.080(24) 3.059(29) 3.010(16) 3.004(15) 2.960(18) 2.950(12) 2.946(11) 2.947(12) H O C-H O C O-C 117.3(15) 115.2(17) 115.5(20) 115.3(8) 114.7(9) 110.4(12) 112.1(9) 112.3(9) 111.7(9) C O 3.314(23) 3.297(30) 3.273(33) 3.224(14) 3.195(14) 3.192(16) 3.174(12) 3.172(11) 3.174(11) H O C-H O C O-C C O 3.541(25) 3.526(30) 3.506(37) 3.557(14) 3.536(14) 3.478(18) 3.458(13) 3.436(13) 3.453(13) H O C-H O C O-C 124.2(15) 123.5(18) 125.7(21) 126.4(7) 127.3(7) 125.4(9) 126.6(7) 126.9(7) 126.5(7) C O 3.426(41) 3.405(47) 3.433(51) 3.389(16) 3.386(22) 3.337(33) 3.294(24) 3.310(23) 3.292(23) H O C-H O C O-C 68.2(17) 69.5(19) 70.1(20) 68.2(7) 67.6(9) 66.3(12) 68.0(9) 67.3(8) 67.9(8) C O 3.826(45) 3.717(59) 3.875(77) 3.788(20) 3.745(25) 3.590(40) 3.603(29) 3.584(28) 3.595(28) H O C-H O C O-C 95.3(18) 98.6(19) 98.3(21) 96.1(8) 96.7(9) 98.4(15) 98.0(11) 98.3(10) 97.9(10) intermolecular contact between two molecules of the same type (A-A or B-B) intermolecular contact between two molecules of different types (A-B or B-A) 30