research papers
A high-resolution powder synchrotron X-ray diffraction pattern of the Γ form of D-sorbitol has been recorded at 293 K on the BM1B beamline at the ESRF (Grenoble). The starting model of the structure was found by Monte Carlo simulated annealing. The final structure was obtained through Rietveld refinements performed with soft restraints on interatomic bond lengths and angles. The symmetry is orthorhombic, space group P21212, with 12 molecules within the cell [a = 24.3012 (2), b = 20.5726 (2), c = 4.8672 (1) Å, V = 2433.30 (3) Å3, Z′ = 3, 36 non-H independent atoms]. Crystalline cohesion between neighbouring molecules is achieved by three networks of O—HO hydrogen bonds. The width of the Bragg peaks is interpreted through a microstructural approach in terms of anisotropic strain effects.
Keywords: simulated annealing; Monte Carlo; strain effects; hydrogen bonding; sorbitol; polymorphism.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0021889804016206/hx5008sup1.cif | |
Rietveld powder data file (CIF format) https://doi.org/10.1107/S0021889804016206/hx5008sup2.rtv | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0021889804016206/hx5008sup3.pdf |
CCDC reference: 254343
Computing details top
Data collection: PEAKOC; program(s) used to solve structure: FOX; program(s) used to refine structure: FULLPROF; molecular graphics: ORTEP-3; software used to prepare material for publication: SHELX97 and PARST.
Figures top
(gamma-sorbitol) top
Crystal data top
C6H14O6 | V = 2433.30 (3) Å3 |
Mr = 182.17 | Z = 12 |
Orthorhombic, P21212 | BM01B, ESRF radiation, λ = 0.499570 Å |
Hall symbol: P 2 2ab | µ = 0.13 mm−1 |
a = 24.30122 (17) Å | T = 293 K |
b = 20.57261 (14) Å | white |
c = 4.86719 (3) Å | cylinder, diameter 1.5 mm, ? × ? × ? mm |
Data collection top
BM01B, ESRF diffractometer | Scan method: step |
Radiation source: Synchrotron | Absorption correction: for a cylinder mounted on the ϕ axis ? |
Si(1,1,1) monochromator | Tmin = ?, Tmax = ? |
Specimen mounting: Lindemann Glass Capillary | 2θmin = 1.500°, 2θmax = 28.000°, 2θstep = 0.005° |
Data collection mode: transmission |
Refinement top
Rp = 1.837 | Profile function: pseudo-Voigt |
Rwp = 2.286 | 171 parameters |
Rexp = 1.650 | 63 restraints |
RBragg = 1.662 | |
χ2 = NOT FOUND | Background function: linear interpolation between 43 points |
6424 data points | Preferred orientation correction: March-Dollase function, axis [1,0,0], G1=0.994(1), G2=0 |
Excluded region(s): intensities too low |
Crystal data top
C6H14O6 | V = 2433.30 (3) Å3 |
Mr = 182.17 | Z = 12 |
Orthorhombic, P21212 | BM01B, ESRF radiation, λ = 0.499570 Å |
a = 24.30122 (17) Å | µ = 0.13 mm−1 |
b = 20.57261 (14) Å | T = 293 K |
c = 4.86719 (3) Å | cylinder, diameter 1.5 mm, ? × ? × ? mm |
Data collection top
BM01B, ESRF diffractometer | Absorption correction: for a cylinder mounted on the ϕ axis ? |
Specimen mounting: Lindemann Glass Capillary | Tmin = ?, Tmax = ? |
Data collection mode: transmission | 2θmin = 1.500°, 2θmax = 28.000°, 2θstep = 0.005° |
Scan method: step |
Refinement top
Rp = 1.837 | χ2 = NOT FOUND |
Rwp = 2.286 | 6424 data points |
Rexp = 1.650 | 171 parameters |
RBragg = 1.662 | 63 restraints |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C11 | 0.36472 (15) | 0.51245 (19) | 0.6125 (10) | 0.0326 (5)* | |
C12 | 0.41877 (13) | 0.50350 (11) | 0.4570 (7) | 0.0326 (5)* | |
C13 | 0.41601 (15) | 0.44029 (12) | 0.2907 (6) | 0.0326 (5)* | |
C14 | 0.42261 (14) | 0.38001 (11) | 0.4713 (7) | 0.0326 (5)* | |
C15 | 0.41697 (16) | 0.31586 (11) | 0.3152 (7) | 0.0326 (5)* | |
C16 | 0.42283 (19) | 0.2534 (2) | 0.4798 (10) | 0.0326 (5)* | |
O11 | 0.36953 (15) | 0.56981 (15) | 0.7773 (7) | 0.0326 (5)* | |
O12 | 0.42365 (16) | 0.55813 (15) | 0.2784 (7) | 0.0326 (5)* | |
O13 | 0.46221 (13) | 0.44282 (18) | 0.1099 (8) | 0.0326 (5)* | |
O14 | 0.47456 (11) | 0.37937 (18) | 0.6094 (8) | 0.0326 (5)* | |
O15 | 0.37078 (13) | 0.31704 (18) | 0.1344 (7) | 0.0326 (5)* | |
O16 | 0.37906 (13) | 0.25555 (19) | 0.6723 (7) | 0.0326 (5)* | |
H11A | 0.33360 | 0.51660 | 0.48090 | 0.0326 (5)* | |
H11B | 0.35800 | 0.47360 | 0.73380 | 0.0326 (5)* | |
H12 | 0.45050 | 0.50210 | 0.58810 | 0.0326 (5)* | |
H13 | 0.38090 | 0.43810 | 0.18380 | 0.0326 (5)* | |
H14 | 0.39310 | 0.38130 | 0.61450 | 0.0326 (5)* | |
H15 | 0.44940 | 0.31540 | 0.18870 | 0.0326 (5)* | |
H16A | 0.41950 | 0.21460 | 0.35830 | 0.0326 (5)* | |
H16B | 0.45920 | 0.25210 | 0.57630 | 0.0326 (5)* | |
HO11 | 0.33379 | 0.58747 | 0.75049 | 0.0326 (5)* | |
HO12 | 0.45349 | 0.56125 | 0.27003 | 0.0326 (5)* | |
HO13 | 0.45930 | 0.42230 | −0.03062 | 0.0326 (5)* | |
HO14 | 0.47024 | 0.36535 | 0.75735 | 0.0326 (5)* | |
HO15 | 0.33798 | 0.32362 | 0.20605 | 0.0326 (5)* | |
HO16 | 0.34860 | 0.26271 | 0.60495 | 0.0326 (5)* | |
C21 | 0.10186 (15) | 0.22078 (19) | 0.3416 (9) | 0.0339 (6)* | |
C22 | 0.07691 (11) | 0.27904 (15) | 0.1977 (7) | 0.0339 (6)* | |
C23 | 0.11906 (12) | 0.31472 (16) | 0.0233 (7) | 0.0339 (6)* | |
C24 | 0.16296 (11) | 0.34940 (16) | 0.1958 (7) | 0.0339 (6)* | |
C25 | 0.20804 (11) | 0.37951 (16) | 0.0202 (7) | 0.0339 (6)* | |
C26 | 0.25327 (19) | 0.41219 (17) | 0.1870 (10) | 0.0339 (6)* | |
O21 | 0.06459 (13) | 0.19346 (18) | 0.5354 (7) | 0.0339 (6)* | |
O22 | 0.03162 (13) | 0.25723 (19) | 0.0365 (7) | 0.0339 (6)* | |
O23 | 0.09113 (15) | 0.36106 (15) | −0.1473 (7) | 0.0339 (6)* | |
O24 | 0.13952 (14) | 0.40146 (15) | 0.3502 (7) | 0.0339 (6)* | |
O25 | 0.23291 (16) | 0.32992 (16) | −0.1452 (8) | 0.0339 (6)* | |
O26 | 0.27807 (15) | 0.36617 (14) | 0.3701 (8) | 0.0339 (6)* | |
H21A | 0.11220 | 0.18740 | 0.20330 | 0.0339 (6)* | |
H21B | 0.13600 | 0.23520 | 0.44210 | 0.0339 (6)* | |
H22 | 0.06270 | 0.30980 | 0.34040 | 0.0339 (6)* | |
H23 | 0.13780 | 0.28240 | −0.09810 | 0.0339 (6)* | |
H24 | 0.17990 | 0.31740 | 0.32540 | 0.0339 (6)* | |
H25 | 0.19110 | 0.41260 | −0.10430 | 0.0339 (6)* | |
H26A | 0.28180 | 0.43010 | 0.06020 | 0.0339 (6)* | |
H26B | 0.23710 | 0.44880 | 0.29640 | 0.0339 (6)* | |
HO21 | 0.06385 | 0.15432 | 0.55250 | 0.0339 (6)* | |
HO22 | 0.04755 | 0.23840 | −0.14054 | 0.0339 (6)* | |
HO23 | 0.10669 | 0.35595 | −0.28832 | 0.0339 (6)* | |
HO24 | 0.13148 | 0.41060 | 0.50022 | 0.0339 (6)* | |
HO25 | 0.21536 | 0.32980 | −0.26875 | 0.0339 (6)* | |
HO26 | 0.28423 | 0.38638 | 0.50852 | 0.0339 (6)* | |
C31 | 0.4478 (2) | 0.10689 (15) | 0.9420 (12) | 0.0521 (6)* | |
C32 | 0.41397 (10) | 0.05197 (16) | 0.8158 (7) | 0.0521 (6)* | |
C33 | 0.36336 (11) | 0.07649 (19) | 0.6578 (7) | 0.0521 (6)* | |
C34 | 0.31614 (11) | 0.10469 (16) | 0.8290 (7) | 0.0521 (6)* | |
C35 | 0.26915 (11) | 0.13216 (16) | 0.6570 (7) | 0.0521 (6)* | |
C36 | 0.22303 (14) | 0.1562 (2) | 0.8399 (9) | 0.0521 (6)* | |
O31 | 0.48932 (15) | 0.0791 (2) | 1.1122 (8) | 0.0521 (6)* | |
O32 | 0.45244 (14) | 0.0260 (2) | 0.6236 (7) | 0.0521 (6)* | |
O33 | 0.34700 (17) | 0.02917 (17) | 0.4592 (7) | 0.0521 (6)* | |
O34 | 0.29366 (15) | 0.05072 (15) | 0.9758 (9) | 0.0521 (6)* | |
O35 | 0.29054 (15) | 0.18453 (16) | 0.5000 (9) | 0.0521 (6)* | |
O36 | 0.24119 (16) | 0.20219 (16) | 1.0400 (8) | 0.0521 (6)* | |
H31A | 0.46510 | 0.13340 | 0.79340 | 0.0521 (6)* | |
H31B | 0.42330 | 0.13560 | 1.05490 | 0.0521 (6)* | |
H32 | 0.40350 | 0.01890 | 0.95710 | 0.0521 (6)* | |
H33 | 0.37720 | 0.11400 | 0.54720 | 0.0521 (6)* | |
H34 | 0.33020 | 0.13830 | 0.95990 | 0.0521 (6)* | |
H35 | 0.25490 | 0.09770 | 0.53100 | 0.0521 (6)* | |
H36A | 0.19430 | 0.17720 | 0.72210 | 0.0521 (6)* | |
H36B | 0.20640 | 0.11820 | 0.93680 | 0.0521 (6)* | |
HO31 | 0.52151 | 0.07209 | 1.03566 | 0.0521 (6)* | |
HO32 | 0.43449 | 0.00434 | 0.43925 | 0.0521 (6)* | |
HO33 | 0.32332 | 0.00529 | 0.52058 | 0.0521 (6)* | |
HO34 | 0.30225 | 0.05733 | 1.11887 | 0.0521 (6)* | |
HO35 | 0.31953 | 0.17597 | 0.44736 | 0.0521 (6)* | |
HO36 | 0.23909 | 0.23850 | 0.95956 | 0.0521 (6)* |
Geometric parameters (Å, º) top
C11—O11 | 1.432 (5) | C25—O25 | 1.433 (5) |
C11—C12 | 1.527 (5) | C25—C26 | 1.523 (5) |
C11—H11A | 0.995 | C25—H25 | 1.000 |
C11—H11B | 1.007 | C26—O26 | 1.433 (5) |
C12—O12 | 1.426 (4) | C26—H26A | 0.999 |
C12—C13 | 1.533 (4) | C26—H26B | 1.002 |
C12—H12 | 1.001 | O21—HO21 | 0.810 |
C13—O13 | 1.427 (5) | O22—HO22 | 1.021 |
C13—C14 | 1.528 (4) | O23—HO23 | 0.791 |
C13—H13 | 1.000 | O24—HO24 | 0.779 |
C14—O14 | 1.430 (4) | O25—HO25 | 0.737 |
C14—C15 | 1.529 (4) | O26—HO26 | 0.806 |
C14—H14 | 1.001 | C31—O31 | 1.425 (6) |
C15—O15 | 1.426 (5) | C31—C32 | 1.526 (5) |
C15—C16 | 1.520 (5) | C31—H31A | 0.999 |
C15—H15 | 1.000 | C31—H31B | 1.002 |
C16—O16 | 1.418 (6) | C32—O32 | 1.426 (4) |
C16—H16A | 0.998 | C32—C33 | 1.536 (4) |
C16—H16B | 1.002 | C32—H32 | 1.000 |
O11—HO11 | 0.951 | C33—O33 | 1.428 (5) |
O12—HO12 | 0.729 | C33—C34 | 1.532 (4) |
O13—HO13 | 0.807 | C33—H33 | 0.999 |
O14—HO14 | 0.783 | C34—O34 | 1.429 (5) |
O15—HO15 | 0.880 | C34—C35 | 1.524 (4) |
O16—HO16 | 0.823 | C34—H34 | 1.000 |
C21—O21 | 1.424 (5) | C35—O35 | 1.420 (5) |
C21—C22 | 1.515 (5) | C35—C36 | 1.514 (5) |
C21—H21A | 0.994 | C35—H35 | 0.999 |
C21—H21B | 1.007 | C36—O36 | 1.428 (6) |
C22—O22 | 1.424 (4) | C36—H36A | 1.001 |
C22—C23 | 1.520 (4) | C36—H36B | 0.999 |
C22—H22 | 1.001 | O31—HO31 | 0.878 |
C23—O23 | 1.435 (5) | O32—HO32 | 1.093 |
C23—C24 | 1.534 (4) | O33—HO33 | 0.814 |
C23—H23 | 0.999 | O34—HO34 | 0.739 |
C24—O24 | 1.427 (4) | O35—HO35 | 0.770 |
C24—C25 | 1.521 (4) | O36—HO36 | 0.845 |
C24—H24 | 1.000 | ||
O11—C11—C12 | 107.9 (3) | O24—C24—H24 | 109.0 |
O11—C11—H11A | 110.6 | C25—C24—H24 | 109.0 |
C12—C11—H11A | 110.2 | C23—C24—H24 | 109.0 |
O11—C11—H11B | 109.8 | O25—C25—C24 | 109.2 (3) |
C12—C11—H11B | 109.5 | O25—C25—C26 | 108.0 (3) |
H11A—C11—H11B | 108.8 | C24—C25—C26 | 113.6 (3) |
O12—C12—C11 | 106.2 (3) | O25—C25—H25 | 108.5 |
O12—C12—C13 | 110.5 (2) | C24—C25—H25 | 108.7 |
C11—C12—C13 | 109.0 (3) | C26—C25—H25 | 108.6 |
O12—C12—H12 | 110.3 | O26—C26—C25 | 110.1 (4) |
C11—C12—H12 | 110.5 | O26—C26—H26A | 109.6 |
C13—C12—H12 | 110.2 | C25—C26—H26A | 109.5 |
O13—C13—C14 | 107.5 (3) | O26—C26—H26B | 109.3 |
O13—C13—C12 | 105.1 (3) | C25—C26—H26B | 109.4 |
C14—C13—C12 | 112.3 (2) | H26A—C26—H26B | 108.9 |
O13—C13—H13 | 110.6 | C21—O21—HO21 | 118.4 |
C14—C13—H13 | 110.6 | C22—O22—HO22 | 107.0 |
C12—C13—H13 | 110.5 | C23—O23—HO23 | 100.8 |
O14—C14—C13 | 111.7 (3) | C24—O24—HO24 | 140.8 |
O14—C14—C15 | 107.7 (3) | C25—O25—HO25 | 102.5 |
C13—C14—C15 | 113.9 (2) | C26—O26—HO26 | 104.9 |
O14—C14—H14 | 107.8 | O31—C31—C32 | 108.6 (4) |
C13—C14—H14 | 107.7 | O31—C31—H31A | 110.0 |
C15—C14—H14 | 107.7 | C32—C31—H31A | 109.8 |
O15—C15—C16 | 114.4 (3) | O31—C31—H31B | 109.7 |
O15—C15—C14 | 111.2 (3) | C32—C31—H31B | 109.7 |
C16—C15—C14 | 117.3 (2) | H31A—C31—H31B | 109.0 |
O15—C15—H15 | 103.9 | O32—C32—C31 | 100.9 (3) |
C16—C15—H15 | 104.0 | O32—C32—C33 | 108.6 (2) |
C14—C15—H15 | 104.1 | C31—C32—C33 | 112.9 (3) |
O16—C16—C15 | 104.6 (3) | O32—C32—H32 | 111.3 |
O16—C16—H16A | 110.8 | C31—C32—H32 | 111.3 |
C15—C16—H16A | 110.9 | C33—C32—H32 | 111.3 |
O16—C16—H16B | 110.7 | O33—C33—C34 | 114.7 (3) |
C15—C16—H16B | 110.7 | O33—C33—C32 | 109.7 (3) |
H16A—C16—H16B | 109.1 | C34—C33—C32 | 116.9 (2) |
C11—O11—HO11 | 99.4 | O33—C33—H33 | 104.8 |
C12—O12—HO12 | 100.7 | C34—C33—H33 | 104.6 |
C13—O13—HO13 | 115.8 | C32—C33—H33 | 104.7 |
C14—O14—HO14 | 108.5 | O34—C34—C35 | 106.0 (3) |
C15—O15—HO15 | 118.1 | O34—C34—C33 | 105.3 (3) |
C16—O16—HO16 | 114.6 | C35—C34—C33 | 113.7 (2) |
O21—C21—C22 | 111.3 (4) | O34—C34—H34 | 110.4 |
O21—C21—H21A | 109.6 | C35—C34—H34 | 110.4 |
C22—C21—H21A | 109.5 | C33—C34—H34 | 110.6 |
O21—C21—H21B | 108.6 | O35—C35—C36 | 109.8 (3) |
C22—C21—H21B | 108.8 | O35—C35—C34 | 107.6 (3) |
H21A—C21—H21B | 108.9 | C36—C35—C34 | 110.7 (2) |
O22—C22—C21 | 108.4 (3) | O35—C35—H35 | 109.6 |
O22—C22—C23 | 111.4 (2) | C36—C35—H35 | 109.6 |
C21—C22—C23 | 111.8 (3) | C34—C35—H35 | 109.5 |
O22—C22—H22 | 108.3 | O36—C36—C35 | 112.9 (4) |
C21—C22—H22 | 108.5 | O36—C36—H36A | 108.7 |
C23—C22—H22 | 108.4 | C35—C36—H36A | 108.7 |
O23—C23—C22 | 109.0 (3) | O36—C36—H36B | 108.8 |
O23—C23—C24 | 109.7 (3) | C35—C36—H36B | 108.7 |
C22—C23—C24 | 112.8 (2) | H36A—C36—H36B | 109.0 |
O23—C23—H23 | 108.4 | C31—O31—HO31 | 116.8 |
C22—C23—H23 | 108.4 | C32—O32—HO32 | 115.4 |
C24—C23—H23 | 108.4 | C33—O33—HO33 | 111.1 |
O24—C24—C25 | 106.1 (3) | C34—O34—HO34 | 102.7 |
O24—C24—C23 | 111.1 (3) | C35—O35—HO35 | 109.9 |
C25—C24—C23 | 112.5 (2) | C36—O36—HO36 | 104.5 |
O11—C11—C12—O12 | −64.0 (4) | O23—C23—C24—C25 | −63.8 (3) |
O11—C11—C12—C13 | 176.9 (3) | C22—C23—C24—C25 | 174.5 (2) |
O12—C12—C13—O13 | 51.7 (3) | O24—C24—C25—O25 | −179.0 (3) |
C11—C12—C13—O13 | 168.0 (3) | C23—C24—C25—O25 | −57.3 (3) |
O12—C12—C13—C14 | 168.3 (3) | O24—C24—C25—C26 | 60.4 (4) |
C11—C12—C13—C14 | −75.4 (3) | C23—C24—C25—C26 | −177.9 (3) |
O13—C13—C14—O14 | 54.4 (3) | O25—C25—C26—O26 | −63.1 (4) |
C12—C13—C14—O14 | −60.8 (3) | C24—C25—C26—O26 | 58.3 (4) |
O13—C13—C14—C15 | −68.0 (3) | O31—C31—C32—O32 | −71.7 (4) |
C12—C13—C14—C15 | 176.9 (3) | O31—C31—C32—C33 | 172.6 (3) |
O14—C14—C15—O15 | −170.0 (3) | O32—C32—C33—O33 | 45.5 (4) |
C13—C14—C15—O15 | −45.4 (4) | C31—C32—C33—O33 | 156.6 (3) |
O14—C14—C15—C16 | 55.6 (4) | O32—C32—C33—C34 | 178.4 (3) |
C13—C14—C15—C16 | −179.8 (3) | C31—C32—C33—C34 | −70.6 (4) |
O15—C15—C16—O16 | −71.0 (4) | O33—C33—C34—O34 | 62.3 (4) |
C14—C15—C16—O16 | 62.0 (4) | C32—C33—C34—O34 | −68.3 (3) |
O21—C21—C22—O22 | −65.5 (4) | O33—C33—C34—C35 | −53.4 (4) |
O21—C21—C22—C23 | 171.3 (3) | C32—C33—C34—C35 | 176.1 (3) |
O22—C22—C23—O23 | 47.6 (4) | O34—C34—C35—O35 | −177.9 (3) |
C21—C22—C23—O23 | 169.0 (3) | C33—C34—C35—O35 | −62.6 (3) |
O22—C22—C23—C24 | 169.7 (3) | O34—C34—C35—C36 | 62.1 (4) |
C21—C22—C23—C24 | −69.0 (3) | C33—C34—C35—C36 | 177.4 (3) |
O23—C23—C24—O24 | 55.0 (3) | O35—C35—C36—O36 | −63.9 (4) |
C22—C23—C24—O24 | −66.7 (3) | C34—C35—C36—O36 | 54.7 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O12—HO12···O13i | 0.729 (4) | 2.193 (3) | 2.892 (5) | 161.0 (3) |
O13—HO13···O14ii | 0.807 (4) | 1.997 (4) | 2.780 (5) | 163.5 (3) |
O15—HO15···O26 | 0.880 (3) | 1.877 (3) | 2.723 (5) | 160.4 (2) |
O21—HO21···O12iii | 0.810 (4) | 2.165 (3) | 2.942 (5) | 160.9 (3) |
O22—HO22···O21ii | 1.021 (3) | 1.875 (4) | 2.883 (5) | 168.8 (2) |
O24—HO24···O23iv | 0.779 (3) | 2.224 (3) | 2.838 (5) | 136.3 (3) |
O26—HO26···O25iv | 0.806 (3) | 2.397 (4) | 2.707 (5) | 104.0 (3) |
O33—HO33···O24iii | 0.814 (4) | 2.403 (3) | 2.805 (4) | 111.5 (2) |
O34—HO34···O33iv | 0.739 (4) | 2.065 (4) | 2.722 (5) | 148.5 (3) |
O35—HO35···O16 | 0.770 (4) | 2.444 (3) | 2.732 (5) | 103.8 (3) |
Symmetry codes: (i) −x+1, −y+1, z; (ii) x, y, z−1; (iii) −x+1/2, y−1/2, −z+1; (iv) x, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | C6H14O6 |
Mr | 182.17 |
Crystal system, space group | Orthorhombic, P21212 |
Temperature (K) | 293 |
a, b, c (Å) | 24.30122 (17), 20.57261 (14), 4.86719 (3) |
V (Å3) | 2433.30 (3) |
Z | 12 |
Radiation type | BM01B, ESRF, λ = 0.499570 Å |
µ (mm−1) | 0.13 |
Specimen shape, size (mm) | Cylinder, diameter 1.5 mm, ? × ? × ? |
Data collection | |
Data collection method | BM01B, ESRF |
Specimen mounting | Lindemann Glass Capillary |
Data collection mode | Transmission |
Scan method | Step |
2θ values (°) | 2θmin = 1.500 2θmax = 28.000 2θstep = 0.005 |
Refinement | |
R factors and goodness of fit | Rp = 1.837, Rwp = 2.286, Rexp = 1.650, RBragg = 1.662, χ2 = NOT FOUND |
No. of data points | 6424 |
No. of parameters | 171 |
No. of restraints | 63 |
Computer programs: PEAKOC, FOX, FULLPROF, ORTEP-3, SHELX97 and PARST.
Selected geometric parameters (Å, º) top
C11—O11 | 1.432 (5) | C24—O24 | 1.427 (4) |
C11—C12 | 1.527 (5) | C24—C25 | 1.521 (4) |
C12—O12 | 1.426 (4) | C25—O25 | 1.433 (5) |
C12—C13 | 1.533 (4) | C25—C26 | 1.523 (5) |
C13—O13 | 1.427 (5) | C26—O26 | 1.433 (5) |
C13—C14 | 1.528 (4) | C31—O31 | 1.425 (6) |
C14—O14 | 1.430 (4) | C31—C32 | 1.526 (5) |
C14—C15 | 1.529 (4) | C32—O32 | 1.426 (4) |
C15—O15 | 1.426 (5) | C32—C33 | 1.536 (4) |
C15—C16 | 1.520 (5) | C33—O33 | 1.428 (5) |
C16—O16 | 1.418 (6) | C33—C34 | 1.532 (4) |
C21—O21 | 1.424 (5) | C34—O34 | 1.429 (5) |
C21—C22 | 1.515 (5) | C34—C35 | 1.524 (4) |
C22—O22 | 1.424 (4) | C35—O35 | 1.420 (5) |
C22—C23 | 1.520 (4) | C35—C36 | 1.514 (5) |
C23—O23 | 1.435 (5) | C36—O36 | 1.428 (6) |
C23—C24 | 1.534 (4) | ||
O11—C11—C12 | 107.9 (3) | O24—C24—C25 | 106.1 (3) |
O12—C12—C11 | 106.2 (3) | O24—C24—C23 | 111.1 (3) |
O12—C12—C13 | 110.5 (2) | C25—C24—C23 | 112.5 (2) |
C11—C12—C13 | 109.0 (3) | O25—C25—C24 | 109.2 (3) |
O13—C13—C14 | 107.5 (3) | O25—C25—C26 | 108.0 (3) |
O13—C13—C12 | 105.1 (3) | C24—C25—C26 | 113.6 (3) |
C14—C13—C12 | 112.3 (2) | O26—C26—C25 | 110.1 (4) |
O14—C14—C13 | 111.7 (3) | O31—C31—C32 | 108.6 (4) |
O14—C14—C15 | 107.7 (3) | O32—C32—C31 | 100.9 (3) |
C13—C14—C15 | 113.9 (2) | O32—C32—C33 | 108.6 (2) |
O15—C15—C16 | 114.4 (3) | C31—C32—C33 | 112.9 (3) |
O15—C15—C14 | 111.2 (3) | O33—C33—C34 | 114.7 (3) |
C16—C15—C14 | 117.3 (2) | O33—C33—C32 | 109.7 (3) |
O16—C16—C15 | 104.6 (3) | C34—C33—C32 | 116.9 (2) |
O21—C21—C22 | 111.3 (4) | O34—C34—C35 | 106.0 (3) |
O22—C22—C21 | 108.4 (3) | O34—C34—C33 | 105.3 (3) |
O22—C22—C23 | 111.4 (2) | C35—C34—C33 | 113.7 (2) |
C21—C22—C23 | 111.8 (3) | O35—C35—C36 | 109.8 (3) |
O23—C23—C22 | 109.0 (3) | O35—C35—C34 | 107.6 (3) |
O23—C23—C24 | 109.7 (3) | C36—C35—C34 | 110.7 (2) |
C22—C23—C24 | 112.8 (2) | O36—C36—C35 | 112.9 (4) |
O11—C11—C12—O12 | −64.0 (4) | O23—C23—C24—C25 | −63.8 (3) |
O11—C11—C12—C13 | 176.9 (3) | C22—C23—C24—C25 | 174.5 (2) |
O12—C12—C13—O13 | 51.7 (3) | O24—C24—C25—O25 | −179.0 (3) |
C11—C12—C13—O13 | 168.0 (3) | C23—C24—C25—O25 | −57.3 (3) |
O12—C12—C13—C14 | 168.3 (3) | O24—C24—C25—C26 | 60.4 (4) |
C11—C12—C13—C14 | −75.4 (3) | C23—C24—C25—C26 | −177.9 (3) |
O13—C13—C14—O14 | 54.4 (3) | O25—C25—C26—O26 | −63.1 (4) |
C12—C13—C14—O14 | −60.8 (3) | C24—C25—C26—O26 | 58.3 (4) |
O13—C13—C14—C15 | −68.0 (3) | O31—C31—C32—O32 | −71.7 (4) |
C12—C13—C14—C15 | 176.9 (3) | O31—C31—C32—C33 | 172.6 (3) |
O14—C14—C15—O15 | −170.0 (3) | O32—C32—C33—O33 | 45.5 (4) |
C13—C14—C15—O15 | −45.4 (4) | C31—C32—C33—O33 | 156.6 (3) |
O14—C14—C15—C16 | 55.6 (4) | O32—C32—C33—C34 | 178.4 (3) |
C13—C14—C15—C16 | −179.8 (3) | C31—C32—C33—C34 | −70.6 (4) |
O15—C15—C16—O16 | −71.0 (4) | O33—C33—C34—O34 | 62.3 (4) |
C14—C15—C16—O16 | 62.0 (4) | C32—C33—C34—O34 | −68.3 (3) |
O21—C21—C22—O22 | −65.5 (4) | O33—C33—C34—C35 | −53.4 (4) |
O21—C21—C22—C23 | 171.3 (3) | C32—C33—C34—C35 | 176.1 (3) |
O22—C22—C23—O23 | 47.6 (4) | O34—C34—C35—O35 | −177.9 (3) |
C21—C22—C23—O23 | 169.0 (3) | C33—C34—C35—O35 | −62.6 (3) |
O22—C22—C23—C24 | 169.7 (3) | O34—C34—C35—C36 | 62.1 (4) |
C21—C22—C23—C24 | −69.0 (3) | C33—C34—C35—C36 | 177.4 (3) |
O23—C23—C24—O24 | 55.0 (3) | O35—C35—C36—O36 | −63.9 (4) |
C22—C23—C24—O24 | −66.7 (3) | C34—C35—C36—O36 | 54.7 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O12—HO12···O13i | 0.729 (4) | 2.193 (3) | 2.892 (5) | 161.0 (3) |
O13—HO13···O14ii | 0.807 (4) | 1.997 (4) | 2.780 (5) | 163.5 (3) |
O15—HO15···O26 | 0.880 (3) | 1.877 (3) | 2.723 (5) | 160.4 (2) |
O21—HO21···O12iii | 0.810 (4) | 2.165 (3) | 2.942 (5) | 160.9 (3) |
O22—HO22···O21ii | 1.021 (3) | 1.875 (4) | 2.883 (5) | 168.8 (2) |
O24—HO24···O23iv | 0.779 (3) | 2.224 (3) | 2.838 (5) | 136.3 (3) |
O26—HO26···O25iv | 0.806 (3) | 2.397 (4) | 2.707 (5) | 104.0 (3) |
O33—HO33···O24iii | 0.814 (4) | 2.403 (3) | 2.805 (4) | 111.5 (2) |
O34—HO34···O33iv | 0.739 (4) | 2.065 (4) | 2.722 (5) | 148.5 (3) |
O35—HO35···O16 | 0.770 (4) | 2.444 (3) | 2.732 (5) | 103.8 (3) |
Symmetry codes: (i) −x+1, −y+1, z; (ii) x, y, z−1; (iii) −x+1/2, y−1/2, −z+1; (iv) x, y, z+1. |