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Structural changes of the raffinose crystal on dehydration from the pentahydrate to the tetrahydrate were investigated by single-crystal time-of-flight neutron diffraction. It was revealed that during the dehydration, rearrangement occurs in the hydrogen bonds related to the lost water molecule, while the symmetry of the crystal structure is retained. The hydrogen-bonding status of raffinose pentahydrate and tetrahydrate were discussed comprehensively according to Jeffrey's hydrogen-bonding classification. It was shown that the water molecules are hydrogen bonded to the surrounding molecules by moderate O—H
O hydrogen bonds and weak C—HO hydrogen bonds, and the number of these two types of hydrogen bonds determines the water molecules that are removed by dehydration. The lattice constant c showed a significant decrease on dehydration and further dehydration leads to loss of crystallinity of the raffinose crystals.
O hydrogen bonds and weak C—HO hydrogen bonds, and the number of these two types of hydrogen bonds determines the water molecules that are removed by dehydration. The lattice constant c showed a significant decrease on dehydration and further dehydration leads to loss of crystallinity of the raffinose crystals.Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229622010828/wv3010sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S2053229622010828/wv3010Isup2.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S2053229622010828/wv3010IIsup3.hkl |
CCDC references: 2218959; 2218960
Computing details top
For both structures, data collection: STARGazer (Ohhara, 2009); cell refinement: STARGazer (Ohhara, 2009); data reduction: STARGazer (Ohhara, 2009); program(s) used to solve structure: JANA2006 (Petricek, 2014); program(s) used to refine structure: JANA2006 (Petricek, 2014); molecular graphics: Mercury (Macrae, 2008).
(I) top
Crystal data top
| C18H32O16·5H2O | F(000) = 337.812 |
| Mr = 594.5 | Dx = 1.499 Mg m−3 |
| Orthorhombic, P212121 | Neutron radiation, λ = 1 Å |
| Hall symbol: P 2ac 2ab | Cell parameters from 551 reflections |
| a = 8.8921 (13) Å | θ = 8.1–82.0° |
| b = 12.2495 (12) Å | µ = 0 mm−1 |
| c = 23.798 (3) Å | T = 120 K |
| V = 2592.1 (5) Å3 | Block, colorless |
| Z = 4 | 2 × 1 × 0.5 mm |
Data collection top
| Time-of-flight Laue-type single crystal neutron diffractometer | 5953 reflections with I > 4σ(I) |
| Radiation source: spallation neutron | Rint = 0.158 |
| None monochromator | θmax = 82.0°, θmin = 8.1° |
| Detector resolution: 4 pixels mm-1 | h = −22→21 |
| time–of–flight Laue method scans | k = −30→30 |
| 27274 measured reflections | l = −55→59 |
| 27274 independent reflections |
Refinement top
| Refinement on F | All H-atom parameters refined |
| R[F > 3σ(F)] = 0.070 | Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2) |
| wR(F) = 0.061 | (Δ/σ)max = 0.016 |
| S = 2.06 | Δρmax = 1.77 e Å−3 |
| 5953 reflections | Δρmin = −1.86 e Å−3 |
| 736 parameters | Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974) |
| 0 restraints | Extinction coefficient: 4.0 (4) |
| 0 constraints | Absolute structure: 1082 of Friedel pairs used in the refinement |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| C_1 | 0.2236 (4) | 0.3181 (2) | 0.35724 (12) | 0.0054 (8) | |
| C_2 | 0.1079 (4) | 0.3937 (2) | 0.38483 (13) | 0.0079 (8) | |
| C_3 | 0.1397 (4) | 0.5132 (2) | 0.36910 (12) | 0.0061 (8) | |
| C_4 | 0.3031 (4) | 0.5417 (2) | 0.38352 (12) | 0.0065 (8) | |
| C_5 | 0.4111 (4) | 0.4597 (2) | 0.35726 (12) | 0.0062 (8) | |
| C_6 | 0.5724 (4) | 0.4784 (2) | 0.37501 (13) | 0.0087 (9) | |
| C_1' | 0.7229 (4) | 0.5058 (2) | 0.45516 (13) | 0.0067 (8) | |
| C_2' | 0.7338 (4) | 0.4718 (2) | 0.51695 (13) | 0.0070 (8) | |
| C_3' | 0.6236 (4) | 0.5367 (2) | 0.55311 (12) | 0.0069 (8) | |
| C_4' | 0.6471 (4) | 0.6596 (2) | 0.54294 (13) | 0.0081 (8) | |
| C_5' | 0.6315 (4) | 0.6832 (2) | 0.48014 (13) | 0.0077 (8) | |
| C_6' | 0.6646 (5) | 0.8016 (2) | 0.46484 (14) | 0.0104 (9) | |
| C_1'' | 0.1152 (5) | 0.2114 (2) | 0.22528 (13) | 0.0114 (9) | |
| C_2'' | 0.2504 (4) | 0.2389 (2) | 0.26202 (12) | 0.0075 (8) | |
| C_3'' | 0.3917 (4) | 0.2743 (2) | 0.22997 (12) | 0.0065 (8) | |
| C_4'' | 0.5172 (4) | 0.2364 (2) | 0.26855 (13) | 0.0094 (9) | |
| C_5'' | 0.4542 (5) | 0.1276 (2) | 0.28896 (14) | 0.0108 (9) | |
| C_6'' | 0.5075 (5) | 0.0917 (3) | 0.34601 (14) | 0.0113 (9) | |
| O_1 | 0.2006 (5) | 0.3250 (2) | 0.29911 (14) | 0.0074 (10) | |
| O_2 | −0.0399 (5) | 0.3615 (3) | 0.37109 (15) | 0.0099 (10) | |
| O_3 | 0.0447 (5) | 0.5848 (3) | 0.39998 (15) | 0.0101 (10) | |
| O_4 | 0.3437 (5) | 0.6460 (3) | 0.36162 (15) | 0.0118 (10) | |
| O_5 | 0.3705 (5) | 0.3504 (2) | 0.37385 (13) | 0.0068 (9) | |
| O_6 | 0.5817 (5) | 0.4719 (3) | 0.43501 (15) | 0.0073 (9) | |
| O_2' | 0.7153 (6) | 0.3582 (3) | 0.52394 (17) | 0.0134 (11) | |
| O_3' | 0.6461 (5) | 0.5147 (3) | 0.61082 (15) | 0.0114 (10) | |
| O_4' | 0.7885 (6) | 0.6959 (3) | 0.56416 (15) | 0.0109 (10) | |
| O_5' | 0.7426 (5) | 0.6212 (3) | 0.44975 (14) | 0.0085 (9) | |
| O_6' | 0.5531 (5) | 0.8738 (3) | 0.48588 (16) | 0.0106 (10) | |
| O_1'' | 0.1517 (6) | 0.1272 (3) | 0.18730 (15) | 0.0135 (11) | |
| O_2'' | 0.2927 (5) | 0.1444 (3) | 0.29121 (16) | 0.0084 (9) | |
| O_3'' | 0.3883 (6) | 0.3872 (3) | 0.21853 (16) | 0.0123 (10) | |
| O_4'' | 0.6641 (5) | 0.2312 (3) | 0.24396 (16) | 0.0147 (11) | |
| O_6'' | 0.4543 (6) | −0.0149 (3) | 0.36066 (18) | 0.0148 (12) | |
| Hc_1 | 0.2114 (10) | 0.2347 (4) | 0.3728 (3) | 0.0194 (19) | |
| Hc_2 | 0.1197 (10) | 0.3845 (5) | 0.4306 (3) | 0.022 (2) | |
| Hc_3 | 0.1225 (10) | 0.5262 (5) | 0.3238 (3) | 0.021 (2) | |
| Hc_4 | 0.3172 (9) | 0.5398 (5) | 0.4292 (2) | 0.0178 (19) | |
| Hc_5 | 0.4042 (10) | 0.4652 (5) | 0.3113 (3) | 0.0189 (19) | |
| H'c_6 | 0.6455 (9) | 0.4155 (5) | 0.3563 (3) | 0.023 (2) | |
| Hc_6 | 0.6089 (10) | 0.5602 (5) | 0.3604 (3) | 0.024 (2) | |
| Hc_1' | 0.8121 (9) | 0.4689 (5) | 0.4301 (3) | 0.020 (2) | |
| Hc_2' | 0.8503 (9) | 0.4898 (5) | 0.5324 (3) | 0.023 (2) | |
| Hc_3' | 0.5082 (10) | 0.5167 (5) | 0.5405 (3) | 0.024 (2) | |
| Hc_4' | 0.5621 (9) | 0.7059 (5) | 0.5668 (3) | 0.022 (2) | |
| Hc_5' | 0.5179 (9) | 0.6614 (5) | 0.4663 (3) | 0.020 (2) | |
| Hc_6' | 0.7764 (10) | 0.8250 (6) | 0.4799 (4) | 0.030 (3) | |
| H'c_6' | 0.6634 (11) | 0.8099 (5) | 0.4187 (3) | 0.029 (3) | |
| Hc_1'' | 0.0825 (11) | 0.2842 (5) | 0.2007 (3) | 0.026 (2) | |
| Hc_2'' | 0.0227 (11) | 0.1885 (6) | 0.2519 (3) | 0.034 (3) | |
| Hc_3'' | 0.3995 (10) | 0.2265 (5) | 0.1907 (3) | 0.022 (2) | |
| Hc_4'' | 0.5270 (10) | 0.2920 (5) | 0.3042 (3) | 0.021 (2) | |
| Hc_5'' | 0.4726 (9) | 0.0637 (5) | 0.2574 (3) | 0.0183 (19) | |
| Hc_6'' | 0.4749 (12) | 0.1515 (5) | 0.3771 (3) | 0.033 (3) | |
| H'c_6'' | 0.6293 (11) | 0.0869 (6) | 0.3458 (3) | 0.028 (2) | |
| Ho_2 | −0.0636 (9) | 0.3787 (5) | 0.3305 (3) | 0.021 (2) | |
| Ho_3 | −0.0352 (11) | 0.6070 (5) | 0.3756 (3) | 0.027 (2) | |
| Ho_4 | 0.3127 (10) | 0.7036 (5) | 0.3882 (3) | 0.023 (2) | |
| Ho_2' | 0.6184 (11) | 0.3332 (5) | 0.5086 (3) | 0.026 (2) | |
| Ho_3' | 0.5791 (11) | 0.4535 (5) | 0.6205 (3) | 0.029 (3) | |
| Ho_4' | 0.8723 (9) | 0.6641 (5) | 0.5433 (3) | 0.023 (2) | |
| Ho_6' | 0.5567 (10) | 0.8798 (5) | 0.5273 (3) | 0.023 (2) | |
| Ho_1'' | 0.1667 (10) | 0.0595 (5) | 0.2081 (3) | 0.025 (2) | |
| Ho_3'' | 0.4556 (10) | 0.4064 (5) | 0.1879 (3) | 0.023 (2) | |
| Ho_4'' | 0.6595 (10) | 0.1942 (5) | 0.2082 (3) | 0.025 (2) | |
| Ho_6'' | 0.3422 (11) | −0.0125 (6) | 0.3661 (3) | 0.027 (2) | |
| O_w1 | 0.2037 (6) | 0.4159 (3) | 0.53565 (18) | 0.0208 (14) | |
| H_w11 | 0.1455 (12) | 0.4816 (6) | 0.5359 (3) | 0.035 (3) | |
| H_w12 | 0.1292 (11) | 0.3570 (6) | 0.5340 (3) | 0.029 (2) | |
| O_w2 | 0.9102 (6) | 0.1348 (3) | 0.37989 (18) | 0.0150 (12) | |
| H_w21 | 0.9212 (10) | 0.2141 (5) | 0.3775 (3) | 0.025 (2) | |
| H_w22 | 0.8450 (12) | 0.1198 (6) | 0.4095 (3) | 0.032 (3) | |
| O_w3 | 0.8525 (6) | 0.4164 (3) | 0.26701 (16) | 0.0139 (11) | |
| H_w31 | 0.9305 (10) | 0.4342 (6) | 0.2399 (3) | 0.028 (2) | |
| H_w32 | 0.7906 (11) | 0.3573 (6) | 0.2520 (3) | 0.032 (3) | |
| O_w4 | 0.4815 (6) | 0.2510 (3) | 0.47488 (18) | 0.0144 (12) | |
| H_w41 | 0.3855 (10) | 0.2173 (5) | 0.4844 (3) | 0.026 (2) | |
| H_w42 | 0.4583 (12) | 0.2993 (6) | 0.4446 (3) | 0.033 (3) | |
| O_w5 | 0.1027 (6) | 0.5006 (3) | 0.2172 (2) | 0.0190 (13) | |
| H_w51 | 0.1106 (12) | 0.5484 (6) | 0.1860 (3) | 0.033 (3) | |
| H_w52 | 0.2002 (12) | 0.4625 (6) | 0.2199 (3) | 0.034 (3) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C_1 | 0.0044 (16) | 0.0065 (11) | 0.0053 (12) | 0.0001 (11) | 0.0001 (14) | −0.0009 (9) |
| C_2 | 0.0073 (17) | 0.0094 (11) | 0.0072 (13) | 0.0023 (12) | 0.0019 (16) | 0.0005 (9) |
| C_3 | 0.0049 (16) | 0.0069 (11) | 0.0064 (12) | −0.0003 (11) | 0.0014 (14) | −0.0004 (9) |
| C_4 | 0.0071 (17) | 0.0070 (11) | 0.0055 (12) | 0.0027 (12) | −0.0004 (14) | 0.0005 (9) |
| C_5 | 0.0047 (16) | 0.0079 (11) | 0.0061 (12) | 0.0009 (11) | −0.0004 (14) | −0.0009 (9) |
| C_6 | 0.0086 (18) | 0.0085 (12) | 0.0091 (14) | 0.0011 (12) | 0.0024 (14) | −0.0002 (9) |
| C_1' | 0.0042 (16) | 0.0075 (11) | 0.0085 (13) | −0.0023 (12) | 0.0015 (14) | −0.0010 (9) |
| C_2' | 0.0057 (17) | 0.0047 (10) | 0.0107 (13) | 0.0017 (11) | −0.0030 (14) | −0.0004 (9) |
| C_3' | 0.0078 (17) | 0.0059 (10) | 0.0072 (12) | −0.0012 (12) | −0.0003 (15) | 0.0019 (9) |
| C_4' | 0.0100 (19) | 0.0069 (11) | 0.0074 (13) | −0.0007 (12) | 0.0012 (15) | −0.0018 (9) |
| C_5' | 0.0065 (17) | 0.0071 (11) | 0.0093 (14) | −0.0004 (12) | 0.0029 (15) | −0.0003 (9) |
| C_6' | 0.011 (2) | 0.0072 (11) | 0.0130 (15) | 0.0012 (13) | 0.0015 (16) | 0.0001 (10) |
| C_1'' | 0.016 (2) | 0.0081 (12) | 0.0107 (14) | 0.0006 (14) | −0.0019 (17) | −0.0023 (10) |
| C_2'' | 0.0091 (18) | 0.0071 (11) | 0.0062 (12) | −0.0018 (11) | 0.0006 (15) | −0.0020 (9) |
| C_3'' | 0.0065 (16) | 0.0064 (10) | 0.0065 (12) | −0.0008 (11) | 0.0009 (14) | −0.0007 (9) |
| C_4'' | 0.0110 (19) | 0.0085 (12) | 0.0087 (13) | 0.0012 (12) | −0.0013 (16) | −0.0020 (10) |
| C_5'' | 0.015 (2) | 0.0078 (12) | 0.0102 (14) | 0.0020 (13) | 0.0017 (17) | 0.0001 (10) |
| C_6'' | 0.012 (2) | 0.0114 (13) | 0.0106 (15) | 0.0023 (14) | −0.0042 (16) | 0.0004 (11) |
| O_1 | 0.008 (2) | 0.0076 (13) | 0.0062 (15) | −0.0001 (13) | 0.0008 (16) | 0.0006 (10) |
| O_2 | 0.013 (2) | 0.0096 (14) | 0.0074 (15) | −0.0023 (15) | 0.0031 (18) | −0.0009 (11) |
| O_3 | 0.012 (2) | 0.0104 (14) | 0.0080 (16) | 0.0023 (15) | −0.0016 (18) | −0.0028 (11) |
| O_4 | 0.019 (2) | 0.0075 (13) | 0.0087 (15) | −0.0029 (15) | 0.002 (2) | −0.0006 (11) |
| O_5 | 0.007 (2) | 0.0072 (12) | 0.0060 (14) | 0.0009 (13) | −0.0016 (17) | −0.0020 (10) |
| O_6 | 0.0050 (19) | 0.0095 (13) | 0.0075 (14) | −0.0003 (13) | −0.0042 (16) | −0.0010 (11) |
| O_2' | 0.018 (3) | 0.0080 (15) | 0.0144 (18) | 0.0024 (16) | −0.004 (2) | −0.0002 (12) |
| O_3' | 0.015 (2) | 0.0119 (14) | 0.0073 (15) | −0.0023 (16) | 0.0001 (19) | 0.0021 (11) |
| O_4' | 0.015 (2) | 0.0093 (14) | 0.0084 (15) | 0.0008 (16) | −0.0060 (19) | −0.0053 (12) |
| O_5' | 0.009 (2) | 0.0071 (12) | 0.0097 (15) | 0.0003 (14) | 0.0018 (17) | −0.0025 (10) |
| O_6' | 0.013 (2) | 0.0097 (14) | 0.0090 (16) | 0.0021 (15) | −0.0033 (19) | 0.0022 (11) |
| O_1'' | 0.022 (3) | 0.0100 (14) | 0.0089 (15) | −0.0023 (17) | −0.003 (2) | −0.0028 (11) |
| O_2'' | 0.007 (2) | 0.0064 (12) | 0.0114 (15) | −0.0035 (14) | −0.0019 (17) | 0.0009 (11) |
| O_3'' | 0.013 (2) | 0.0108 (14) | 0.0127 (17) | 0.0002 (16) | 0.000 (2) | 0.0041 (12) |
| O_4'' | 0.015 (2) | 0.0163 (16) | 0.0129 (17) | −0.0029 (17) | 0.005 (2) | −0.0046 (13) |
| O_6'' | 0.018 (3) | 0.0130 (16) | 0.0132 (19) | 0.0019 (17) | 0.009 (2) | 0.0039 (13) |
| Hc_1 | 0.028 (4) | 0.012 (2) | 0.019 (3) | −0.001 (3) | 0.002 (4) | 0.004 (2) |
| Hc_2 | 0.033 (5) | 0.020 (3) | 0.013 (3) | 0.002 (3) | −0.001 (4) | 0.000 (2) |
| Hc_3 | 0.027 (5) | 0.023 (3) | 0.012 (3) | 0.002 (3) | −0.005 (4) | −0.001 (2) |
| Hc_4 | 0.017 (4) | 0.027 (3) | 0.009 (3) | −0.003 (3) | 0.004 (3) | 0.002 (2) |
| Hc_5 | 0.024 (4) | 0.019 (3) | 0.014 (3) | −0.001 (3) | −0.001 (3) | −0.002 (2) |
| H'c_6 | 0.021 (4) | 0.028 (3) | 0.019 (3) | 0.008 (3) | 0.001 (4) | −0.005 (2) |
| Hc_6 | 0.032 (5) | 0.022 (3) | 0.019 (3) | −0.013 (3) | −0.002 (4) | 0.008 (2) |
| Hc_1' | 0.017 (4) | 0.017 (3) | 0.028 (4) | −0.001 (3) | 0.001 (4) | −0.005 (2) |
| Hc_2' | 0.020 (5) | 0.023 (3) | 0.027 (4) | −0.004 (3) | −0.009 (4) | 0.000 (2) |
| Hc_3' | 0.025 (5) | 0.021 (3) | 0.027 (4) | 0.007 (3) | −0.008 (4) | −0.004 (3) |
| Hc_4' | 0.024 (5) | 0.021 (3) | 0.022 (3) | 0.004 (3) | 0.015 (4) | −0.005 (2) |
| Hc_5' | 0.010 (4) | 0.023 (3) | 0.027 (4) | −0.004 (3) | −0.002 (4) | −0.004 (3) |
| Hc_6' | 0.018 (5) | 0.026 (4) | 0.046 (5) | −0.002 (3) | −0.012 (4) | 0.000 (3) |
| H'c_6' | 0.046 (6) | 0.024 (3) | 0.019 (3) | 0.002 (4) | 0.008 (5) | 0.000 (3) |
| Hc_1'' | 0.038 (5) | 0.012 (2) | 0.027 (3) | −0.002 (3) | −0.013 (4) | 0.000 (2) |
| Hc_2'' | 0.039 (6) | 0.030 (4) | 0.032 (4) | −0.001 (4) | 0.001 (5) | −0.004 (3) |
| Hc_3'' | 0.030 (5) | 0.025 (3) | 0.012 (3) | 0.007 (3) | 0.001 (4) | −0.002 (2) |
| Hc_4'' | 0.019 (4) | 0.025 (3) | 0.020 (3) | −0.001 (3) | −0.003 (4) | −0.009 (2) |
| Hc_5'' | 0.020 (4) | 0.014 (3) | 0.021 (3) | 0.001 (3) | 0.004 (4) | −0.004 (2) |
| Hc_6'' | 0.052 (7) | 0.026 (3) | 0.021 (3) | 0.005 (4) | −0.014 (5) | −0.007 (3) |
| H'c_6'' | 0.024 (5) | 0.029 (3) | 0.032 (4) | 0.002 (4) | 0.000 (4) | 0.005 (3) |
| Ho_2 | 0.019 (4) | 0.028 (3) | 0.017 (3) | −0.001 (3) | 0.000 (4) | 0.003 (2) |
| Ho_3 | 0.030 (5) | 0.026 (3) | 0.025 (4) | 0.008 (3) | −0.012 (4) | 0.003 (3) |
| Ho_4 | 0.034 (5) | 0.014 (2) | 0.021 (3) | −0.002 (3) | 0.005 (4) | −0.007 (2) |
| Ho_2' | 0.027 (5) | 0.020 (3) | 0.032 (4) | 0.001 (3) | 0.004 (4) | 0.001 (3) |
| Ho_3' | 0.047 (6) | 0.017 (3) | 0.024 (3) | −0.010 (3) | 0.007 (4) | 0.007 (2) |
| Ho_4' | 0.015 (4) | 0.023 (3) | 0.032 (4) | 0.001 (3) | 0.011 (4) | −0.012 (3) |
| Ho_6' | 0.027 (5) | 0.028 (3) | 0.013 (3) | 0.001 (3) | −0.003 (4) | −0.004 (2) |
| Ho_1'' | 0.036 (5) | 0.014 (3) | 0.026 (3) | −0.001 (3) | −0.005 (4) | 0.002 (2) |
| Ho_3'' | 0.022 (4) | 0.025 (3) | 0.022 (3) | −0.006 (3) | 0.001 (4) | 0.002 (3) |
| Ho_4'' | 0.026 (5) | 0.030 (3) | 0.019 (3) | 0.008 (4) | 0.003 (4) | −0.010 (3) |
| Ho_6'' | 0.020 (5) | 0.035 (4) | 0.026 (4) | 0.004 (4) | 0.005 (4) | 0.003 (3) |
| O_w1 | 0.027 (3) | 0.0150 (17) | 0.020 (2) | 0.005 (2) | 0.000 (2) | 0.0032 (15) |
| H_w11 | 0.041 (6) | 0.023 (4) | 0.040 (5) | 0.004 (4) | −0.010 (5) | 0.002 (3) |
| H_w12 | 0.029 (5) | 0.021 (3) | 0.037 (4) | −0.006 (4) | −0.005 (5) | 0.000 (3) |
| O_w2 | 0.015 (2) | 0.0104 (15) | 0.020 (2) | 0.0007 (16) | −0.004 (2) | −0.0017 (14) |
| H_w21 | 0.029 (5) | 0.012 (2) | 0.035 (4) | −0.004 (3) | 0.004 (4) | −0.001 (2) |
| H_w22 | 0.048 (7) | 0.027 (4) | 0.022 (3) | 0.007 (4) | 0.006 (5) | 0.004 (3) |
| O_w3 | 0.014 (2) | 0.0166 (16) | 0.0114 (17) | −0.0015 (18) | 0.001 (2) | −0.0011 (13) |
| H_w31 | 0.028 (5) | 0.034 (4) | 0.022 (4) | 0.004 (4) | 0.014 (4) | 0.006 (3) |
| H_w32 | 0.040 (6) | 0.022 (3) | 0.034 (4) | −0.003 (4) | −0.007 (5) | −0.005 (3) |
| O_w4 | 0.017 (3) | 0.0091 (15) | 0.0169 (19) | −0.0024 (16) | −0.005 (2) | 0.0020 (13) |
| H_w41 | 0.024 (5) | 0.027 (3) | 0.026 (4) | −0.005 (4) | 0.003 (4) | 0.002 (3) |
| H_w42 | 0.044 (6) | 0.026 (3) | 0.028 (4) | −0.008 (4) | −0.007 (5) | 0.008 (3) |
| O_w5 | 0.014 (2) | 0.0203 (19) | 0.023 (2) | 0.0008 (19) | 0.005 (2) | 0.0097 (16) |
| H_w51 | 0.040 (6) | 0.035 (4) | 0.025 (4) | −0.001 (4) | 0.004 (5) | 0.014 (3) |
| H_w52 | 0.038 (6) | 0.028 (4) | 0.037 (5) | 0.002 (4) | −0.007 (5) | 0.007 (3) |
Geometric parameters (Å, º) top
| C_1—C_2 | 1.532 (4) | C_2''—C_3'' | 1.532 (5) |
| C_1—O_1 | 1.400 (3) | C_2''—O_1 | 1.445 (4) |
| C_1—O_5 | 1.422 (5) | C_2''—O_2'' | 1.402 (5) |
| C_1—Hc_1 | 1.093 (6) | C_3''—C_4'' | 1.517 (4) |
| C_2—C_3 | 1.537 (4) | C_3''—O_3'' | 1.410 (4) |
| C_2—O_2 | 1.410 (6) | C_3''—Hc_3'' | 1.106 (7) |
| C_2—Hc_2 | 1.101 (8) | C_4''—C_5'' | 1.526 (4) |
| C_3—C_4 | 1.533 (5) | C_4''—O_4'' | 1.432 (6) |
| C_3—O_3 | 1.423 (5) | C_4''—Hc_4'' | 1.092 (7) |
| C_3—Hc_3 | 1.100 (8) | C_5''—C_6'' | 1.503 (4) |
| C_4—C_5 | 1.523 (4) | C_5''—O_2'' | 1.452 (6) |
| C_4—O_4 | 1.426 (4) | C_5''—Hc_5'' | 1.098 (7) |
| C_4—Hc_4 | 1.095 (5) | C_6''—O_6'' | 1.432 (5) |
| C_5—C_6 | 1.512 (5) | C_6''—Hc_6'' | 1.081 (8) |
| C_5—O_5 | 1.442 (4) | C_6''—H'c_6'' | 1.082 (10) |
| C_5—Hc_5 | 1.099 (8) | O_2—Ho_2 | 1.011 (9) |
| C_6—O_6 | 1.432 (3) | O_3—Ho_3 | 0.956 (9) |
| C_6—H'c_6 | 1.102 (8) | O_4—Ho_4 | 0.986 (8) |
| C_6—Hc_6 | 1.109 (7) | O_2'—Ho_2' | 0.987 (10) |
| C_1'—C_2' | 1.532 (3) | O_3'—Ho_3' | 0.986 (8) |
| C_1'—O_6 | 1.407 (5) | O_4'—Ho_4' | 0.977 (9) |
| C_1'—O_5' | 1.430 (4) | O_6'—Ho_6' | 0.989 (9) |
| C_1'—Hc_1' | 1.091 (8) | O_1''—Ho_1'' | 0.975 (7) |
| C_2'—C_3' | 1.527 (4) | O_3''—Ho_3'' | 0.974 (9) |
| C_2'—O_2' | 1.411 (4) | O_4''—Ho_4'' | 0.966 (8) |
| C_2'—Hc_2' | 1.121 (9) | O_6''—Ho_6'' | 1.007 (10) |
| C_3'—C_4' | 1.539 (4) | O_w1—H_w11 | 0.954 (9) |
| C_3'—O_3' | 1.414 (3) | O_w1—H_w12 | 0.982 (9) |
| C_3'—Hc_3' | 1.098 (9) | H_w11—H_w12 | 1.534 (10) |
| C_4'—C_5' | 1.529 (3) | O_w2—H_w21 | 0.978 (7) |
| C_4'—O_4' | 1.427 (6) | O_w2—H_w22 | 0.931 (9) |
| C_4'—Hc_4' | 1.103 (8) | H_w21—H_w22 | 1.540 (10) |
| C_5'—C_6' | 1.524 (4) | O_w3—H_w31 | 0.969 (10) |
| C_5'—O_5' | 1.440 (5) | O_w3—H_w32 | 0.975 (9) |
| C_5'—Hc_5' | 1.095 (9) | H_w31—H_w32 | 1.580 (12) |
| C_6'—O_6' | 1.420 (6) | O_w4—H_w41 | 0.979 (10) |
| C_6'—Hc_6' | 1.092 (10) | O_w4—H_w42 | 0.956 (9) |
| C_6'—H'c_6' | 1.102 (8) | H_w41—H_w42 | 1.526 (10) |
| C_1''—C_2'' | 1.524 (5) | O_w5—H_w51 | 0.948 (8) |
| C_1''—O_1'' | 1.410 (4) | O_w5—H_w52 | 0.985 (10) |
| C_1''—Hc_1'' | 1.107 (7) | H_w51—H_w52 | 1.544 (11) |
| C_1''—Hc_2'' | 1.073 (9) | ||
| C_2—C_1—O_1 | 106.8 (3) | O_6'—C_6'—H'c_6' | 106.6 (5) |
| C_2—C_1—O_5 | 109.2 (2) | Hc_6'—C_6'—H'c_6' | 108.4 (7) |
| C_2—C_1—Hc_1 | 110.5 (5) | C_2''—C_1''—O_1'' | 110.4 (4) |
| O_1—C_1—O_5 | 113.2 (3) | C_2''—C_1''—Hc_1'' | 109.6 (5) |
| O_1—C_1—Hc_1 | 112.1 (4) | C_2''—C_1''—Hc_2'' | 108.8 (5) |
| O_5—C_1—Hc_1 | 105.0 (5) | O_1''—C_1''—Hc_1'' | 108.2 (4) |
| C_1—C_2—C_3 | 110.4 (2) | O_1''—C_1''—Hc_2'' | 111.3 (5) |
| C_1—C_2—O_2 | 111.0 (3) | Hc_1''—C_1''—Hc_2'' | 108.6 (7) |
| C_1—C_2—Hc_2 | 107.3 (5) | C_1''—C_2''—C_3'' | 115.1 (2) |
| C_3—C_2—O_2 | 112.4 (3) | C_1''—C_2''—O_1 | 105.7 (3) |
| C_3—C_2—Hc_2 | 108.7 (4) | C_1''—C_2''—O_2'' | 108.3 (3) |
| O_2—C_2—Hc_2 | 106.9 (5) | C_3''—C_2''—O_1 | 110.4 (2) |
| C_2—C_3—C_4 | 109.7 (2) | C_3''—C_2''—O_2'' | 105.1 (3) |
| C_2—C_3—O_3 | 110.6 (3) | O_1—C_2''—O_2'' | 112.5 (3) |
| C_2—C_3—Hc_3 | 110.6 (4) | C_2''—C_3''—C_4'' | 102.5 (2) |
| C_4—C_3—O_3 | 107.9 (3) | C_2''—C_3''—O_3'' | 110.9 (3) |
| C_4—C_3—Hc_3 | 108.3 (5) | C_2''—C_3''—Hc_3'' | 109.0 (5) |
| O_3—C_3—Hc_3 | 109.7 (5) | C_4''—C_3''—O_3'' | 115.7 (3) |
| C_3—C_4—C_5 | 110.8 (2) | C_4''—C_3''—Hc_3'' | 107.4 (5) |
| C_3—C_4—O_4 | 111.2 (3) | O_3''—C_3''—Hc_3'' | 110.9 (4) |
| C_3—C_4—Hc_4 | 109.0 (5) | C_3''—C_4''—C_5'' | 101.0 (3) |
| C_5—C_4—O_4 | 106.4 (3) | C_3''—C_4''—O_4'' | 116.0 (3) |
| C_5—C_4—Hc_4 | 108.7 (4) | C_3''—C_4''—Hc_4'' | 109.7 (5) |
| O_4—C_4—Hc_4 | 110.7 (4) | C_5''—C_4''—O_4'' | 115.2 (3) |
| C_4—C_5—C_6 | 112.6 (2) | C_5''—C_4''—Hc_4'' | 109.0 (4) |
| C_4—C_5—O_5 | 110.0 (3) | O_4''—C_4''—Hc_4'' | 105.8 (6) |
| C_4—C_5—Hc_5 | 109.3 (5) | C_4''—C_5''—C_6'' | 115.4 (3) |
| C_6—C_5—O_5 | 107.6 (3) | C_4''—C_5''—O_2'' | 104.5 (3) |
| C_6—C_5—Hc_5 | 108.8 (5) | C_4''—C_5''—Hc_5'' | 110.4 (4) |
| O_5—C_5—Hc_5 | 108.4 (4) | C_6''—C_5''—O_2'' | 108.7 (3) |
| C_5—C_6—O_6 | 108.9 (3) | C_6''—C_5''—Hc_5'' | 111.3 (4) |
| C_5—C_6—H'c_6 | 109.9 (4) | O_2''—C_5''—Hc_5'' | 105.9 (5) |
| C_5—C_6—Hc_6 | 109.1 (5) | C_5''—C_6''—O_6'' | 112.5 (3) |
| O_6—C_6—H'c_6 | 109.2 (5) | C_5''—C_6''—Hc_6'' | 109.6 (5) |
| O_6—C_6—Hc_6 | 110.2 (4) | C_5''—C_6''—H'c_6'' | 109.1 (5) |
| H'c_6—C_6—Hc_6 | 109.4 (6) | O_6''—C_6''—Hc_6'' | 111.2 (5) |
| C_2'—C_1'—O_6 | 107.7 (3) | O_6''—C_6''—H'c_6'' | 106.3 (5) |
| C_2'—C_1'—O_5' | 110.3 (2) | Hc_6''—C_6''—H'c_6'' | 107.9 (7) |
| C_2'—C_1'—Hc_1' | 111.5 (4) | C_1—O_1—C_2'' | 121.0 (3) |
| O_6—C_1'—O_5' | 111.7 (3) | C_2—O_2—Ho_2 | 110.9 (6) |
| O_6—C_1'—Hc_1' | 109.8 (5) | C_3—O_3—Ho_3 | 107.6 (6) |
| O_5'—C_1'—Hc_1' | 105.7 (4) | C_4—O_4—Ho_4 | 109.6 (5) |
| C_1'—C_2'—C_3' | 111.0 (2) | C_1—O_5—C_5 | 114.3 (3) |
| C_1'—C_2'—O_2' | 111.9 (3) | C_6—O_6—C_1' | 112.1 (3) |
| C_1'—C_2'—Hc_2' | 108.6 (4) | C_2'—O_2'—Ho_2' | 111.4 (5) |
| C_3'—C_2'—O_2' | 111.9 (3) | C_3'—O_3'—Ho_3' | 106.7 (5) |
| C_3'—C_2'—Hc_2' | 107.9 (4) | C_4'—O_4'—Ho_4' | 111.5 (6) |
| O_2'—C_2'—Hc_2' | 105.3 (4) | C_1'—O_5'—C_5' | 113.1 (3) |
| C_2'—C_3'—C_4' | 109.5 (2) | C_6'—O_6'—Ho_6' | 112.0 (6) |
| C_2'—C_3'—O_3' | 110.9 (3) | C_1''—O_1''—Ho_1'' | 109.2 (5) |
| C_2'—C_3'—Hc_3' | 109.3 (4) | C_2''—O_2''—C_5'' | 111.4 (3) |
| C_4'—C_3'—O_3' | 108.7 (2) | C_3''—O_3''—Ho_3'' | 111.6 (5) |
| C_4'—C_3'—Hc_3' | 107.6 (4) | C_4''—O_4''—Ho_4'' | 109.7 (6) |
| O_3'—C_3'—Hc_3' | 110.8 (5) | C_6''—O_6''—Ho_6'' | 109.4 (6) |
| C_3'—C_4'—C_5' | 109.1 (2) | H_w11—O_w1—H_w12 | 104.8 (9) |
| C_3'—C_4'—O_4' | 111.6 (3) | O_w1—H_w11—H_w12 | 38.2 (5) |
| C_3'—C_4'—Hc_4' | 109.2 (4) | O_w1—H_w12—H_w11 | 37.0 (5) |
| C_5'—C_4'—O_4' | 111.6 (3) | H_w21—O_w2—H_w22 | 107.6 (8) |
| C_5'—C_4'—Hc_4' | 110.2 (4) | O_w2—H_w21—H_w22 | 35.2 (5) |
| O_4'—C_4'—Hc_4' | 105.1 (5) | O_w2—H_w22—H_w21 | 37.3 (5) |
| C_4'—C_5'—C_6' | 113.3 (2) | H_w31—O_w3—H_w32 | 108.8 (8) |
| C_4'—C_5'—O_5' | 109.1 (2) | O_w3—H_w31—H_w32 | 35.7 (5) |
| C_4'—C_5'—Hc_5' | 109.3 (4) | O_w3—H_w32—H_w31 | 35.5 (5) |
| C_6'—C_5'—O_5' | 104.5 (3) | H_w41—O_w4—H_w42 | 104.1 (8) |
| C_6'—C_5'—Hc_5' | 109.8 (4) | O_w4—H_w41—H_w42 | 37.4 (5) |
| O_5'—C_5'—Hc_5' | 110.7 (4) | O_w4—H_w42—H_w41 | 38.5 (5) |
| C_5'—C_6'—O_6' | 111.9 (3) | H_w51—O_w5—H_w52 | 106.0 (8) |
| C_5'—C_6'—Hc_6' | 110.3 (5) | O_w5—H_w51—H_w52 | 37.8 (5) |
| C_5'—C_6'—H'c_6' | 108.9 (4) | O_w5—H_w52—H_w51 | 36.2 (5) |
| O_6'—C_6'—Hc_6' | 110.7 (5) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| C_1—Hc_1···O_2′i | 1.093 (6) | 2.709 (8) | 3.560 (5) | 134.4 (5) |
| C_1—Hc_1···O_w2ii | 1.093 (6) | 2.946 (10) | 3.619 (6) | 120.1 (6) |
| C_2—Hc_2···O_w1 | 1.101 (8) | 2.638 (9) | 3.701 (5) | 162.0 (6) |
| C_3—Hc_3···O_w5 | 1.100 (8) | 2.563 (9) | 3.633 (5) | 164.2 (5) |
| C_5—Hc_5···O_3′′ | 1.099 (8) | 2.410 (8) | 3.426 (5) | 153.1 (5) |
| C_6—H′c_6···O_2iii | 1.102 (8) | 2.896 (9) | 3.734 (6) | 132.9 (5) |
| C_6—H′c_6···O_w3 | 1.102 (8) | 2.811 (9) | 3.659 (6) | 133.5 (5) |
| C_6—Hc_6···O_1′′iv | 1.109 (7) | 2.548 (10) | 3.397 (5) | 132.5 (6) |
| C_1′—Hc_1′···C_2iii | 1.091 (8) | 2.988 (8) | 4.051 (5) | 164.8 (5) |
| C_1′—Hc_1′···O_2iii | 1.091 (8) | 2.331 (8) | 3.403 (5) | 166.9 (6) |
| C_1′—Hc_1′···O_3iii | 1.091 (8) | 2.609 (9) | 3.294 (6) | 120.1 (5) |
| C_2′—Hc_2′···O_6′v | 1.121 (9) | 2.497 (8) | 3.412 (5) | 137.9 (5) |
| C_2′—Hc_2′···O_6′′vi | 1.121 (9) | 2.724 (9) | 3.549 (6) | 129.9 (5) |
| C_3′—Hc_3′···O_w1 | 1.098 (9) | 2.976 (10) | 4.038 (6) | 162.5 (5) |
| C_4′—Hc_4′···O_3v | 1.103 (8) | 2.687 (7) | 3.533 (5) | 133.0 (5) |
| C_5′—Hc_5′···O_4 | 1.095 (9) | 2.940 (8) | 3.835 (5) | 139.1 (5) |
| C_5′—Hc_5′···O_4′vii | 1.095 (9) | 2.783 (9) | 3.551 (6) | 127.0 (4) |
| C_1′′—Hc_1′′···O_w5 | 1.107 (7) | 2.686 (7) | 3.550 (4) | 134.4 (5) |
| C_1′′—Hc_2′′···O_w5viii | 1.073 (9) | 2.662 (9) | 3.506 (5) | 135.2 (6) |
| C_3′′—Hc_3′′···O_4ix | 1.106 (7) | 2.778 (9) | 3.572 (5) | 128.4 (6) |
| C_4′′—Hc_4′′···C_5 | 1.092 (7) | 2.623 (7) | 3.583 (4) | 146.3 (6) |
| C_4′′—Hc_4′′···C_6 | 1.092 (7) | 2.866 (7) | 3.931 (4) | 164.8 (5) |
| C_4′′—Hc_4′′···O_5 | 1.092 (7) | 2.280 (8) | 3.153 (4) | 135.5 (7) |
| C_5′′—Hc_5′′···O_3′′ix | 1.098 (7) | 2.556 (8) | 3.266 (5) | 121.4 (5) |
| C_6′′—Hc_6′′···O_5 | 1.081 (8) | 2.609 (7) | 3.459 (5) | 135.1 (5) |
| C_6′′—Hc_6′′···O_w4 | 1.081 (8) | 2.628 (8) | 3.643 (5) | 156.2 (6) |
| C_6′′—H′c_6′′···O_w2 | 1.082 (10) | 2.694 (10) | 3.708 (7) | 156.0 (6) |
| O_2—Ho_2···O_w3ii | 1.011 (9) | 1.747 (9) | 2.740 (7) | 166.0 (8) |
| O_3—Ho_3···C_1′′x | 0.956 (9) | 2.812 (8) | 3.649 (5) | 146.7 (7) |
| O_3—Ho_3···O_1′′x | 0.956 (9) | 1.838 (9) | 2.763 (6) | 162.1 (7) |
| O_4—Ho_4···C_4′vii | 0.986 (8) | 2.770 (8) | 3.727 (4) | 163.7 (7) |
| O_4—Ho_4···O_4′vii | 0.986 (8) | 1.687 (8) | 2.666 (5) | 171.3 (9) |
| O_2′—Ho_2′···O_w4 | 0.987 (10) | 1.769 (9) | 2.721 (7) | 160.9 (7) |
| O_3′—Ho_3′···O_w2i | 0.986 (8) | 1.850 (9) | 2.793 (6) | 159.2 (7) |
| O_3′—Ho_3′···O_w5xi | 0.986 (8) | 2.867 (9) | 3.368 (6) | 112.3 (5) |
| O_4′—Ho_4′···C_6′v | 0.977 (9) | 2.640 (9) | 3.415 (7) | 136.4 (6) |
| O_4′—Ho_4′···O_6′v | 0.977 (9) | 1.812 (9) | 2.772 (7) | 167.0 (7) |
| O_6′—Ho_6′···C_3v | 0.989 (9) | 2.887 (8) | 3.797 (5) | 153.3 (6) |
| O_6′—Ho_6′···O_3v | 0.989 (9) | 1.787 (9) | 2.763 (7) | 168.8 (7) |
| O_1′′—Ho_1′′···O_w3ix | 0.975 (7) | 1.858 (7) | 2.802 (5) | 162.0 (8) |
| O_3′′—Ho_3′′···C_6′′iv | 0.974 (9) | 2.431 (7) | 3.081 (5) | 123.8 (6) |
| O_3′′—Ho_3′′···O_6′′iv | 0.974 (9) | 1.704 (9) | 2.636 (7) | 159.0 (7) |
| O_4′′—Ho_4′′···C_4ix | 0.966 (8) | 2.892 (7) | 3.831 (5) | 164.3 (6) |
| O_4′′—Ho_4′′···O_4ix | 0.966 (8) | 1.763 (7) | 2.722 (5) | 171.3 (6) |
| O_6′′—Ho_6′′···C_2′i | 1.007 (10) | 2.986 (8) | 3.549 (6) | 116.3 (6) |
| O_6′′—Ho_6′′···C_3′i | 1.007 (10) | 2.749 (9) | 3.595 (6) | 141.9 (6) |
| O_6′′—Ho_6′′···O_3′i | 1.007 (10) | 1.827 (10) | 2.823 (7) | 169.5 (7) |
| O_w1—H_w11···C_6′vii | 0.954 (9) | 2.661 (8) | 3.478 (4) | 143.9 (7) |
| O_w1—H_w11···O_6′vii | 0.954 (9) | 2.022 (9) | 2.949 (6) | 163.1 (7) |
| O_w1—H_w12···O_w4i | 0.982 (9) | 1.875 (9) | 2.854 (6) | 175.4 (7) |
| O_w2—H_w21···C_2iii | 0.978 (7) | 2.763 (8) | 3.628 (5) | 147.8 (7) |
| O_w2—H_w21···O_2iii | 0.978 (7) | 1.845 (7) | 2.820 (5) | 174.6 (9) |
| O_w2—H_w22···O_w1vi | 0.931 (9) | 1.863 (9) | 2.791 (7) | 175.1 (8) |
| O_w3—H_w31···O_w5iii | 0.969 (10) | 1.820 (10) | 2.724 (7) | 154.0 (7) |
| O_w3—H_w32···C_4′′ | 0.975 (9) | 2.877 (9) | 3.708 (6) | 143.8 (7) |
| O_w3—H_w32···O_4′′ | 0.975 (9) | 1.922 (9) | 2.873 (6) | 164.2 (7) |
| O_w4—H_w41···C_2′i | 0.979 (10) | 2.679 (7) | 3.512 (5) | 143.3 (6) |
| O_w4—H_w41···O_2′i | 0.979 (10) | 1.781 (10) | 2.719 (7) | 159.4 (7) |
| O_w4—H_w42···C_1 | 0.956 (9) | 2.954 (9) | 3.712 (6) | 137.2 (7) |
| O_w4—H_w42···C_5 | 0.956 (9) | 2.890 (8) | 3.842 (5) | 174.1 (7) |
| O_w4—H_w42···C_6 | 0.956 (9) | 2.931 (8) | 3.750 (5) | 144.5 (7) |
| O_w4—H_w42···O_5 | 0.956 (9) | 1.957 (8) | 2.869 (5) | 159.0 (7) |
| O_w4—H_w42···O_6 | 0.956 (9) | 2.394 (9) | 3.003 (5) | 121.2 (7) |
| O_w5—H_w51···O_w2iv | 0.948 (8) | 1.901 (8) | 2.838 (6) | 169.0 (9) |
| O_w5—H_w52···C_2′′ | 0.985 (10) | 2.951 (8) | 3.625 (5) | 126.5 (6) |
| O_w5—H_w52···C_3′′ | 0.985 (10) | 2.877 (8) | 3.792 (5) | 154.9 (7) |
| O_w5—H_w52···O_1 | 0.985 (10) | 2.528 (8) | 3.030 (5) | 111.5 (6) |
| O_w5—H_w52···O_3′′ | 0.985 (10) | 1.912 (10) | 2.895 (7) | 175.2 (7) |
| Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x−1, y, z; (iii) x+1, y, z; (iv) −x+1, y+1/2, −z+1/2; (v) x+1/2, −y+3/2, −z+1; (vi) x+1/2, −y+1/2, −z+1; (vii) x−1/2, −y+3/2, −z+1; (viii) −x, y−1/2, −z+1/2; (ix) −x+1, y−1/2, −z+1/2; (x) −x, y+1/2, −z+1/2; (xi) −x+1/2, −y+1, z+1/2. |
(II) top
Crystal data top
| C18H32O16·4H2O | F(000) = 344.512 |
| Mr = 576.5 | Dx = 1.461 Mg m−3 |
| Orthorhombic, P212121 | Neutron radiation, λ = 1 Å |
| Hall symbol: P 2ac 2ab | Cell parameters from 180 reflections |
| a = 8.987 (2) Å | θ = 7.8–82.1° |
| b = 12.3973 (15) Å | µ = 0 mm−1 |
| c = 23.528 (4) Å | T = 298 K |
| V = 2621.3 (9) Å3 | Block, colorless |
| Z = 4 | 2 × 1 × 0.5 mm |
Data collection top
| Time-of-flight Laue-type single crystal neutron diffractometer | 3544 reflections with I > 4σ(I) |
| Radiation source: spallation neutron | Rint = 0.126 |
| None monochromator | θmax = 82.1°, θmin = 7.8° |
| Detector resolution: 4 pixels mm-1 | h = −17→17 |
| time–of–flight Laue method scans | k = −24→24 |
| 19956 measured reflections | l = −32→47 |
| 19956 independent reflections |
Refinement top
| Refinement on F | 0 constraints |
| R[F > 3σ(F)] = 0.075 | All H-atom parameters refined |
| wR(F) = 0.068 | Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2) |
| S = 2.61 | (Δ/σ)max = 0.045 |
| 3544 reflections | Δρmax = 0.96 e Å−3 |
| 668 parameters | Δρmin = −0.93 e Å−3 |
| 0 restraints | Absolute structure: 794 of Friedel pairs used in the refinement |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| C_1 | 0.2168 (8) | 0.3253 (4) | 0.3577 (3) | 0.0183 (19) | |
| C_2 | 0.1015 (8) | 0.4014 (4) | 0.3830 (3) | 0.021 (2) | |
| C_3 | 0.1383 (8) | 0.5194 (4) | 0.3667 (3) | 0.021 (2) | |
| C_4 | 0.2973 (8) | 0.5470 (4) | 0.3827 (3) | 0.019 (2) | |
| C_5 | 0.4054 (8) | 0.4639 (4) | 0.3582 (3) | 0.020 (2) | |
| C_6 | 0.5639 (8) | 0.4817 (6) | 0.3752 (3) | 0.023 (2) | |
| C_1' | 0.7127 (8) | 0.5083 (4) | 0.4556 (3) | 0.021 (2) | |
| C_2' | 0.7281 (9) | 0.4711 (5) | 0.5178 (3) | 0.026 (2) | |
| C_3' | 0.6228 (9) | 0.5358 (5) | 0.5551 (3) | 0.027 (2) | |
| C_4' | 0.6435 (8) | 0.6577 (4) | 0.5458 (3) | 0.024 (2) | |
| C_5' | 0.6280 (9) | 0.6817 (4) | 0.4825 (3) | 0.020 (2) | |
| C_6' | 0.6517 (10) | 0.7986 (5) | 0.4673 (3) | 0.030 (3) | |
| C_1'' | 0.1234 (10) | 0.2113 (5) | 0.2260 (3) | 0.032 (3) | |
| C_2'' | 0.2557 (7) | 0.2424 (4) | 0.2638 (2) | 0.021 (2) | |
| C_3'' | 0.3960 (8) | 0.2772 (4) | 0.2320 (3) | 0.023 (2) | |
| C_4'' | 0.5198 (8) | 0.2398 (5) | 0.2716 (3) | 0.029 (2) | |
| C_5'' | 0.4542 (8) | 0.1313 (4) | 0.2930 (3) | 0.024 (2) | |
| C_6'' | 0.5096 (12) | 0.0945 (6) | 0.3500 (3) | 0.038 (3) | |
| O_1 | 0.2005 (9) | 0.3286 (5) | 0.2986 (3) | 0.024 (2) | |
| O_2 | −0.0426 (11) | 0.3723 (6) | 0.3661 (4) | 0.033 (3) | |
| O_3 | 0.0413 (11) | 0.5929 (6) | 0.3966 (4) | 0.034 (3) | |
| O_4 | 0.3402 (10) | 0.6501 (6) | 0.3608 (3) | 0.032 (3) | |
| O_5 | 0.3633 (9) | 0.3585 (4) | 0.3762 (3) | 0.019 (2) | |
| O_6 | 0.5739 (9) | 0.4760 (5) | 0.4354 (3) | 0.027 (3) | |
| O_2' | 0.7067 (13) | 0.3591 (7) | 0.5227 (4) | 0.041 (3) | |
| O_3' | 0.6480 (12) | 0.5120 (7) | 0.6133 (3) | 0.043 (3) | |
| O_4' | 0.7813 (11) | 0.6917 (6) | 0.5676 (4) | 0.033 (3) | |
| O_5' | 0.7330 (9) | 0.6205 (5) | 0.4511 (3) | 0.027 (2) | |
| O_6' | 0.5370 (10) | 0.8663 (6) | 0.4881 (4) | 0.032 (3) | |
| O_1'' | 0.1598 (12) | 0.1243 (6) | 0.1892 (3) | 0.037 (3) | |
| O_2'' | 0.2946 (10) | 0.1508 (5) | 0.2953 (3) | 0.028 (2) | |
| O_3'' | 0.3906 (11) | 0.3872 (6) | 0.2200 (4) | 0.038 (3) | |
| O_4'' | 0.6615 (10) | 0.2323 (7) | 0.2470 (4) | 0.037 (3) | |
| O_6'' | 0.4580 (14) | −0.0132 (6) | 0.3618 (4) | 0.046 (4) | |
| Hc_1 | 0.2037 (17) | 0.2447 (8) | 0.3753 (5) | 0.039 (5) | |
| Hc_2 | 0.1046 (16) | 0.3965 (9) | 0.4287 (6) | 0.042 (5) | |
| Hc_3 | 0.1226 (18) | 0.5293 (9) | 0.3209 (6) | 0.042 (5) | |
| Hc_4 | 0.3083 (16) | 0.5491 (8) | 0.4284 (5) | 0.037 (5) | |
| Hc_5 | 0.4029 (16) | 0.4682 (8) | 0.3108 (5) | 0.031 (4) | |
| H'c_6 | 0.6353 (17) | 0.4190 (12) | 0.3560 (6) | 0.044 (5) | |
| Hc_6 | 0.5982 (18) | 0.5616 (11) | 0.3612 (5) | 0.050 (5) | |
| Hc_1' | 0.8055 (16) | 0.4740 (10) | 0.4294 (6) | 0.040 (5) | |
| Hc_2' | 0.841 (2) | 0.4877 (11) | 0.5311 (6) | 0.047 (5) | |
| Hc_3' | 0.5064 (17) | 0.5148 (9) | 0.5438 (6) | 0.040 (5) | |
| Hc_4' | 0.555 (2) | 0.6994 (9) | 0.5718 (6) | 0.059 (6) | |
| Hc_5' | 0.5142 (19) | 0.6603 (10) | 0.4698 (6) | 0.041 (5) | |
| Hc_6' | 0.7610 (17) | 0.8258 (10) | 0.4835 (7) | 0.052 (6) | |
| H'c_6' | 0.658 (2) | 0.8103 (10) | 0.4216 (7) | 0.052 (6) | |
| Hc_1'' | 0.097 (2) | 0.2808 (10) | 0.1995 (6) | 0.062 (6) | |
| Hc_2'' | 0.0316 (19) | 0.1906 (11) | 0.2546 (7) | 0.054 (6) | |
| Hc_3'' | 0.4021 (18) | 0.2271 (9) | 0.1918 (5) | 0.042 (5) | |
| Hc_4'' | 0.5271 (19) | 0.2936 (10) | 0.3073 (6) | 0.046 (5) | |
| Hc_5'' | 0.4757 (18) | 0.0695 (9) | 0.2616 (6) | 0.046 (5) | |
| Hc_6'' | 0.474 (2) | 0.1520 (11) | 0.3824 (7) | 0.065 (7) | |
| H'c_6'' | 0.632 (3) | 0.0922 (12) | 0.3488 (7) | 0.068 (7) | |
| Ho_2 | −0.060 (2) | 0.3881 (11) | 0.3275 (7) | 0.049 (6) | |
| Ho_3 | −0.046 (2) | 0.6077 (9) | 0.3718 (6) | 0.044 (5) | |
| Ho_4 | 0.3106 (17) | 0.7057 (9) | 0.3863 (5) | 0.037 (5) | |
| Ho_2' | 0.607 (2) | 0.3376 (11) | 0.5114 (8) | 0.063 (7) | |
| Ho_3' | 0.591 (3) | 0.4483 (11) | 0.6232 (7) | 0.093 (9) | |
| Ho_4' | 0.8710 (19) | 0.6660 (10) | 0.5423 (6) | 0.049 (5) | |
| Ho_6' | 0.5405 (18) | 0.8753 (10) | 0.5294 (6) | 0.040 (5) | |
| Ho_1'' | 0.1733 (19) | 0.0587 (10) | 0.2133 (6) | 0.051 (6) | |
| Ho_3'' | 0.456 (2) | 0.4069 (10) | 0.1872 (6) | 0.055 (6) | |
| Ho_4'' | 0.6588 (19) | 0.1972 (10) | 0.2103 (7) | 0.044 (5) | |
| Ho_6'' | 0.352 (2) | −0.0124 (11) | 0.3684 (7) | 0.047 (6) | |
| O_w2 | 0.9091 (15) | 0.1475 (8) | 0.3834 (6) | 0.065 (5) | |
| H_w21 | 0.920 (2) | 0.2222 (13) | 0.3711 (7) | 0.063 (4)* | |
| H_w22 | 0.889 (3) | 0.1509 (15) | 0.4180 (8) | 0.068 (6)* | |
| O_w3 | 0.8538 (15) | 0.4208 (7) | 0.2578 (5) | 0.052 (4) | |
| H_w31 | 0.915 (3) | 0.4328 (17) | 0.2321 (9) | 0.084 (8)* | |
| H_w32 | 0.783 (2) | 0.3609 (13) | 0.2481 (7) | 0.060 (4)* | |
| O_w6 | 0.4094 (14) | 0.3038 (9) | 0.4954 (4) | 0.065 (4) | |
| H_w61 | 0.351 (2) | 0.2415 (15) | 0.4935 (8) | 0.067 (5)* | |
| H_w62 | 0.414 (2) | 0.3382 (15) | 0.4617 (8) | 0.073 (5)* | |
| O_w5 | 0.1083 (18) | 0.5026 (10) | 0.2066 (7) | 0.081 (6) | |
| H_w51 | 0.118 (4) | 0.538 (2) | 0.1823 (11) | 0.108 (10)* | |
| H_w52 | 0.198 (3) | 0.4677 (16) | 0.2152 (9) | 0.084 (6)* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C_1 | 0.016 (4) | 0.016 (3) | 0.022 (4) | −0.005 (3) | 0.003 (3) | −0.003 (2) |
| C_2 | 0.023 (4) | 0.020 (3) | 0.020 (4) | 0.003 (3) | 0.004 (3) | −0.006 (3) |
| C_3 | 0.021 (4) | 0.021 (3) | 0.020 (4) | 0.005 (3) | 0.000 (3) | −0.005 (3) |
| C_4 | 0.022 (4) | 0.018 (3) | 0.017 (3) | −0.002 (3) | 0.002 (3) | −0.002 (2) |
| C_5 | 0.028 (4) | 0.018 (3) | 0.013 (3) | −0.004 (3) | −0.001 (3) | −0.005 (2) |
| C_6 | 0.019 (5) | 0.027 (3) | 0.022 (4) | −0.002 (3) | 0.001 (3) | −0.006 (3) |
| C_1' | 0.022 (4) | 0.019 (3) | 0.023 (4) | 0.004 (3) | −0.001 (4) | −0.006 (2) |
| C_2' | 0.023 (4) | 0.019 (3) | 0.035 (4) | 0.005 (3) | −0.003 (4) | 0.000 (3) |
| C_3' | 0.034 (5) | 0.021 (3) | 0.027 (4) | 0.001 (3) | −0.006 (4) | 0.000 (3) |
| C_4' | 0.027 (5) | 0.016 (3) | 0.029 (4) | 0.005 (3) | 0.010 (4) | −0.003 (2) |
| C_5' | 0.020 (5) | 0.020 (3) | 0.018 (3) | 0.004 (3) | −0.004 (4) | −0.004 (2) |
| C_6' | 0.027 (5) | 0.021 (3) | 0.041 (5) | −0.001 (3) | 0.000 (5) | 0.004 (3) |
| C_1'' | 0.038 (6) | 0.027 (3) | 0.030 (4) | −0.002 (4) | 0.003 (4) | −0.007 (3) |
| C_2'' | 0.025 (4) | 0.019 (3) | 0.018 (3) | −0.005 (3) | 0.002 (3) | −0.001 (2) |
| C_3'' | 0.030 (4) | 0.016 (3) | 0.022 (3) | 0.000 (3) | 0.003 (3) | −0.006 (2) |
| C_4'' | 0.028 (5) | 0.025 (3) | 0.032 (4) | 0.000 (3) | 0.001 (4) | −0.006 (3) |
| C_5'' | 0.024 (4) | 0.018 (3) | 0.030 (4) | 0.005 (3) | −0.002 (3) | −0.007 (3) |
| C_6'' | 0.043 (6) | 0.036 (4) | 0.034 (5) | 0.013 (4) | 0.001 (5) | 0.002 (4) |
| O_1 | 0.028 (5) | 0.021 (3) | 0.024 (4) | 0.001 (3) | 0.000 (4) | −0.003 (3) |
| O_2 | 0.024 (5) | 0.032 (4) | 0.044 (6) | −0.005 (4) | 0.005 (5) | −0.008 (4) |
| O_3 | 0.033 (6) | 0.027 (4) | 0.042 (5) | 0.008 (4) | −0.009 (5) | −0.011 (4) |
| O_4 | 0.039 (6) | 0.026 (4) | 0.031 (5) | −0.004 (4) | 0.012 (5) | 0.002 (3) |
| O_5 | 0.017 (5) | 0.023 (3) | 0.017 (3) | −0.001 (3) | −0.002 (4) | 0.000 (3) |
| O_6 | 0.026 (5) | 0.024 (4) | 0.031 (4) | −0.005 (3) | −0.005 (4) | 0.001 (3) |
| O_2' | 0.046 (6) | 0.028 (4) | 0.048 (5) | 0.012 (5) | −0.021 (6) | −0.005 (4) |
| O_3' | 0.059 (7) | 0.039 (5) | 0.031 (5) | −0.007 (5) | 0.004 (5) | 0.009 (4) |
| O_4' | 0.030 (6) | 0.030 (4) | 0.040 (5) | 0.003 (4) | 0.002 (5) | −0.019 (4) |
| O_5' | 0.022 (5) | 0.034 (4) | 0.023 (4) | 0.001 (3) | 0.002 (4) | −0.001 (3) |
| O_6' | 0.031 (6) | 0.036 (4) | 0.030 (5) | 0.012 (4) | −0.005 (5) | −0.003 (4) |
| O_1'' | 0.056 (7) | 0.029 (4) | 0.027 (5) | −0.002 (5) | −0.006 (5) | −0.011 (3) |
| O_2'' | 0.035 (5) | 0.017 (3) | 0.032 (4) | −0.003 (3) | 0.002 (4) | 0.001 (3) |
| O_3'' | 0.044 (6) | 0.027 (4) | 0.043 (5) | 0.001 (4) | 0.021 (5) | 0.000 (4) |
| O_4'' | 0.020 (5) | 0.049 (5) | 0.042 (6) | 0.001 (4) | 0.010 (5) | −0.010 (4) |
| O_6'' | 0.066 (9) | 0.037 (5) | 0.035 (6) | 0.009 (6) | 0.007 (7) | 0.010 (4) |
| Hc_1 | 0.054 (10) | 0.016 (5) | 0.047 (8) | −0.007 (6) | 0.001 (8) | −0.003 (5) |
| Hc_2 | 0.050 (10) | 0.041 (6) | 0.035 (8) | 0.009 (7) | 0.005 (8) | 0.015 (6) |
| Hc_3 | 0.053 (11) | 0.043 (7) | 0.030 (8) | 0.008 (7) | 0.005 (8) | −0.007 (6) |
| Hc_4 | 0.046 (10) | 0.036 (6) | 0.029 (8) | 0.003 (6) | −0.005 (7) | −0.006 (6) |
| Hc_5 | 0.032 (8) | 0.038 (6) | 0.022 (7) | 0.005 (6) | −0.011 (6) | −0.008 (5) |
| H'c_6 | 0.028 (9) | 0.062 (8) | 0.043 (8) | −0.015 (8) | 0.005 (8) | −0.013 (7) |
| Hc_6 | 0.066 (12) | 0.039 (7) | 0.044 (8) | −0.017 (8) | 0.012 (9) | 0.005 (6) |
| Hc_1' | 0.027 (9) | 0.058 (8) | 0.036 (8) | 0.009 (7) | 0.006 (7) | −0.013 (7) |
| Hc_2' | 0.050 (12) | 0.053 (8) | 0.038 (8) | −0.004 (8) | −0.012 (9) | 0.008 (6) |
| Hc_3' | 0.036 (10) | 0.034 (7) | 0.050 (9) | −0.011 (6) | −0.007 (8) | 0.003 (6) |
| Hc_4' | 0.094 (15) | 0.035 (7) | 0.047 (9) | 0.013 (8) | 0.024 (10) | −0.008 (6) |
| Hc_5' | 0.032 (10) | 0.047 (8) | 0.045 (9) | 0.015 (6) | −0.004 (8) | −0.001 (7) |
| Hc_6' | 0.025 (10) | 0.047 (8) | 0.084 (11) | −0.008 (7) | −0.021 (9) | 0.001 (8) |
| H'c_6' | 0.072 (13) | 0.048 (7) | 0.036 (8) | 0.014 (8) | 0.016 (9) | 0.003 (7) |
| Hc_1'' | 0.100 (16) | 0.031 (6) | 0.055 (9) | 0.015 (8) | −0.050 (11) | −0.009 (7) |
| Hc_2'' | 0.047 (10) | 0.050 (8) | 0.065 (11) | −0.005 (8) | 0.022 (10) | −0.009 (7) |
| Hc_3'' | 0.056 (10) | 0.040 (7) | 0.031 (7) | −0.008 (7) | 0.009 (8) | −0.010 (6) |
| Hc_4'' | 0.054 (11) | 0.047 (7) | 0.037 (8) | −0.012 (8) | 0.008 (8) | −0.014 (6) |
| Hc_5'' | 0.053 (10) | 0.035 (6) | 0.050 (9) | −0.007 (7) | 0.014 (8) | −0.024 (6) |
| Hc_6'' | 0.095 (16) | 0.051 (7) | 0.048 (9) | 0.009 (10) | 0.000 (10) | −0.013 (8) |
| H'c_6'' | 0.078 (16) | 0.061 (10) | 0.064 (12) | 0.000 (11) | −0.027 (12) | 0.018 (8) |
| Ho_2 | 0.051 (12) | 0.044 (8) | 0.054 (10) | −0.007 (8) | −0.008 (11) | 0.001 (8) |
| Ho_3 | 0.050 (11) | 0.031 (6) | 0.049 (9) | 0.005 (7) | −0.026 (9) | −0.001 (6) |
| Ho_4 | 0.044 (11) | 0.027 (6) | 0.039 (8) | −0.001 (6) | 0.008 (7) | −0.002 (6) |
| Ho_2' | 0.046 (12) | 0.029 (7) | 0.114 (15) | −0.025 (8) | −0.006 (12) | 0.003 (8) |
| Ho_3' | 0.18 (2) | 0.040 (7) | 0.059 (10) | −0.053 (12) | −0.014 (14) | 0.002 (8) |
| Ho_4' | 0.042 (11) | 0.044 (7) | 0.060 (9) | 0.004 (7) | 0.011 (10) | −0.021 (7) |
| Ho_6' | 0.042 (10) | 0.050 (7) | 0.029 (8) | −0.006 (7) | −0.006 (8) | −0.007 (6) |
| Ho_1'' | 0.067 (12) | 0.033 (6) | 0.053 (9) | 0.001 (7) | −0.001 (9) | −0.002 (7) |
| Ho_3'' | 0.078 (14) | 0.035 (7) | 0.053 (10) | −0.013 (8) | 0.016 (10) | 0.014 (7) |
| Ho_4'' | 0.041 (10) | 0.039 (7) | 0.051 (10) | 0.000 (7) | −0.003 (9) | −0.003 (7) |
| Ho_6'' | 0.044 (11) | 0.042 (8) | 0.054 (10) | 0.015 (8) | 0.026 (11) | −0.008 (7) |
| O_w2 | 0.068 (9) | 0.040 (5) | 0.088 (9) | −0.010 (5) | −0.016 (8) | −0.005 (6) |
| O_w3 | 0.057 (8) | 0.035 (5) | 0.064 (8) | 0.007 (5) | −0.003 (7) | −0.005 (5) |
| O_w6 | 0.073 (10) | 0.069 (7) | 0.053 (7) | −0.032 (6) | −0.024 (7) | 0.016 (5) |
| O_w5 | 0.075 (11) | 0.054 (6) | 0.114 (12) | 0.011 (7) | 0.009 (10) | 0.028 (7) |
Geometric parameters (Å, º) top
| C_1—C_2 | 1.522 (9) | C_1''—Hc_1'' | 1.090 (15) |
| C_1—O_1 | 1.400 (9) | C_1''—Hc_2'' | 1.095 (18) |
| C_1—O_5 | 1.446 (10) | C_2''—C_3'' | 1.529 (9) |
| C_1—Hc_1 | 1.087 (11) | C_2''—O_1 | 1.435 (9) |
| C_2—C_3 | 1.547 (8) | C_2''—O_2'' | 1.400 (9) |
| C_2—O_2 | 1.401 (12) | C_3''—C_4'' | 1.523 (10) |
| C_2—Hc_2 | 1.078 (15) | C_3''—O_3'' | 1.394 (9) |
| C_3—C_4 | 1.517 (10) | C_3''—Hc_3'' | 1.132 (13) |
| C_3—O_3 | 1.445 (11) | C_4''—C_5'' | 1.553 (9) |
| C_3—Hc_3 | 1.093 (15) | C_4''—O_4'' | 1.401 (12) |
| C_4—C_5 | 1.529 (9) | C_4''—Hc_4'' | 1.074 (15) |
| C_4—O_4 | 1.430 (9) | C_5''—C_6'' | 1.502 (10) |
| C_4—Hc_4 | 1.081 (14) | C_5''—O_2'' | 1.455 (11) |
| C_5—C_6 | 1.496 (10) | C_5''—Hc_5'' | 1.082 (14) |
| C_5—O_5 | 1.425 (8) | C_6''—O_6'' | 1.440 (12) |
| C_5—Hc_5 | 1.115 (13) | C_6''—Hc_6'' | 1.091 (17) |
| C_6—O_6 | 1.422 (10) | C_6''—H'c_6'' | 1.10 (3) |
| C_6—H'c_6 | 1.104 (16) | O_2—Ho_2 | 0.94 (2) |
| C_6—Hc_6 | 1.088 (15) | O_3—Ho_3 | 0.993 (19) |
| C_1'—C_2' | 1.541 (9) | O_4—Ho_4 | 0.952 (15) |
| C_1'—O_6 | 1.393 (11) | O_2'—Ho_2' | 0.97 (2) |
| C_1'—O_5' | 1.408 (9) | O_3'—Ho_3' | 0.97 (2) |
| C_1'—Hc_1' | 1.121 (15) | O_4'—Ho_4' | 1.051 (19) |
| C_2'—C_3' | 1.520 (10) | O_6'—Ho_6' | 0.977 (17) |
| C_2'—O_2' | 1.405 (10) | O_1''—Ho_1'' | 0.999 (15) |
| C_2'—Hc_2' | 1.081 (19) | O_3''—Ho_3'' | 1.000 (19) |
| C_3'—C_4' | 1.538 (8) | O_4''—Ho_4'' | 0.966 (18) |
| C_3'—O_3' | 1.419 (10) | O_6''—Ho_6'' | 0.96 (2) |
| C_3'—Hc_3' | 1.111 (17) | O_w2—H_w21 | 0.98 (2) |
| C_4'—C_5' | 1.526 (9) | O_w2—H_w22 | 0.84 (2) |
| C_4'—O_4' | 1.405 (12) | H_w21—H_w22 | 1.44 (3) |
| C_4'—Hc_4' | 1.127 (18) | O_w3—H_w31 | 0.83 (3) |
| C_5'—C_6' | 1.508 (8) | O_w3—H_w32 | 1.00 (2) |
| C_5'—O_5' | 1.418 (10) | H_w31—H_w32 | 1.53 (3) |
| C_5'—Hc_5' | 1.099 (18) | O_w6—H_w61 | 0.93 (2) |
| C_6'—O_6' | 1.416 (11) | O_w6—H_w62 | 0.90 (2) |
| C_6'—Hc_6' | 1.106 (18) | H_w61—H_w62 | 1.52 (3) |
| C_6'—H'c_6' | 1.086 (17) | O_w5—H_w51 | 0.73 (3) |
| C_1''—C_2'' | 1.534 (10) | O_w5—H_w52 | 0.94 (3) |
| C_1''—O_1'' | 1.421 (10) | H_w51—H_w52 | 1.37 (4) |
| C_2—C_1—O_1 | 107.4 (5) | C_5'—C_6'—H'c_6' | 111.7 (8) |
| C_2—C_1—O_5 | 109.0 (5) | O_6'—C_6'—Hc_6' | 110.3 (10) |
| C_2—C_1—Hc_1 | 110.4 (9) | O_6'—C_6'—H'c_6' | 107.6 (11) |
| O_1—C_1—O_5 | 112.6 (6) | Hc_6'—C_6'—H'c_6' | 104.6 (15) |
| O_1—C_1—Hc_1 | 113.2 (8) | C_2''—C_1''—O_1'' | 111.4 (7) |
| O_5—C_1—Hc_1 | 104.2 (9) | C_2''—C_1''—Hc_1'' | 107.5 (11) |
| C_1—C_2—C_3 | 110.1 (5) | C_2''—C_1''—Hc_2'' | 106.7 (10) |
| C_1—C_2—O_2 | 111.0 (6) | O_1''—C_1''—Hc_1'' | 107.5 (10) |
| C_1—C_2—Hc_2 | 109.7 (9) | O_1''—C_1''—Hc_2'' | 111.7 (10) |
| C_3—C_2—O_2 | 111.8 (6) | Hc_1''—C_1''—Hc_2'' | 112.0 (15) |
| C_3—C_2—Hc_2 | 107.2 (8) | C_1''—C_2''—C_3'' | 115.3 (5) |
| O_2—C_2—Hc_2 | 107.0 (10) | C_1''—C_2''—O_1 | 104.5 (6) |
| C_2—C_3—C_4 | 110.7 (5) | C_1''—C_2''—O_2'' | 107.2 (5) |
| C_2—C_3—O_3 | 110.3 (6) | C_3''—C_2''—O_1 | 110.7 (5) |
| C_2—C_3—Hc_3 | 108.8 (8) | C_3''—C_2''—O_2'' | 106.4 (6) |
| C_4—C_3—O_3 | 107.8 (6) | O_1—C_2''—O_2'' | 112.9 (6) |
| C_4—C_3—Hc_3 | 109.9 (10) | C_2''—C_3''—C_4'' | 102.5 (5) |
| O_3—C_3—Hc_3 | 109.3 (9) | C_2''—C_3''—O_3'' | 110.3 (6) |
| C_3—C_4—C_5 | 110.6 (5) | C_2''—C_3''—Hc_3'' | 107.1 (9) |
| C_3—C_4—O_4 | 111.5 (6) | C_4''—C_3''—O_3'' | 116.6 (6) |
| C_3—C_4—Hc_4 | 109.8 (9) | C_4''—C_3''—Hc_3'' | 107.9 (9) |
| C_5—C_4—O_4 | 107.2 (6) | O_3''—C_3''—Hc_3'' | 111.7 (8) |
| C_5—C_4—Hc_4 | 109.5 (8) | C_3''—C_4''—C_5'' | 100.6 (5) |
| O_4—C_4—Hc_4 | 108.1 (8) | C_3''—C_4''—O_4'' | 115.6 (7) |
| C_4—C_5—C_6 | 113.8 (5) | C_3''—C_4''—Hc_4'' | 109.5 (10) |
| C_4—C_5—O_5 | 109.7 (6) | C_5''—C_4''—O_4'' | 114.9 (6) |
| C_4—C_5—Hc_5 | 109.4 (8) | C_5''—C_4''—Hc_4'' | 107.9 (9) |
| C_6—C_5—O_5 | 108.0 (6) | O_4''—C_4''—Hc_4'' | 108.0 (11) |
| C_6—C_5—Hc_5 | 106.2 (9) | C_4''—C_5''—C_6'' | 115.3 (6) |
| O_5—C_5—Hc_5 | 109.6 (7) | C_4''—C_5''—O_2'' | 104.0 (5) |
| C_5—C_6—O_6 | 108.6 (6) | C_4''—C_5''—Hc_5'' | 108.9 (9) |
| C_5—C_6—H'c_6 | 109.9 (10) | C_6''—C_5''—O_2'' | 110.1 (6) |
| C_5—C_6—Hc_6 | 108.9 (10) | C_6''—C_5''—Hc_5'' | 109.6 (9) |
| O_6—C_6—H'c_6 | 109.6 (9) | O_2''—C_5''—Hc_5'' | 108.6 (10) |
| O_6—C_6—Hc_6 | 109.1 (9) | C_5''—C_6''—O_6'' | 110.3 (7) |
| H'c_6—C_6—Hc_6 | 110.7 (12) | C_5''—C_6''—Hc_6'' | 109.1 (11) |
| C_2'—C_1'—O_6 | 108.6 (6) | C_5''—C_6''—H'c_6'' | 108.4 (11) |
| C_2'—C_1'—O_5' | 110.8 (5) | O_6''—C_6''—Hc_6'' | 112.1 (12) |
| C_2'—C_1'—Hc_1' | 110.0 (9) | O_6''—C_6''—H'c_6'' | 107.6 (11) |
| O_6—C_1'—O_5' | 112.0 (6) | Hc_6''—C_6''—H'c_6'' | 109.3 (16) |
| O_6—C_1'—Hc_1' | 111.7 (9) | C_1—O_1—C_2'' | 120.6 (6) |
| O_5'—C_1'—Hc_1' | 103.7 (9) | C_2—O_2—Ho_2 | 112.1 (14) |
| C_1'—C_2'—C_3' | 109.5 (5) | C_3—O_3—Ho_3 | 107.8 (11) |
| C_1'—C_2'—O_2' | 111.1 (6) | C_4—O_4—Ho_4 | 110.2 (10) |
| C_1'—C_2'—Hc_2' | 107.6 (9) | C_1—O_5—C_5 | 114.4 (6) |
| C_3'—C_2'—O_2' | 112.9 (7) | C_6—O_6—C_1' | 112.4 (6) |
| C_3'—C_2'—Hc_2' | 108.4 (9) | C_2'—O_2'—Ho_2' | 112.1 (12) |
| O_2'—C_2'—Hc_2' | 107.1 (10) | C_3'—O_3'—Ho_3' | 108.4 (13) |
| C_2'—C_3'—C_4' | 111.2 (6) | C_4'—O_4'—Ho_4' | 112.3 (11) |
| C_2'—C_3'—O_3' | 110.4 (7) | C_1'—O_5'—C_5' | 113.8 (6) |
| C_2'—C_3'—Hc_3' | 108.9 (9) | C_6'—O_6'—Ho_6' | 112.8 (12) |
| C_4'—C_3'—O_3' | 108.8 (6) | C_1''—O_1''—Ho_1'' | 107.4 (10) |
| C_4'—C_3'—Hc_3' | 108.0 (8) | C_2''—O_2''—C_5'' | 111.2 (6) |
| O_3'—C_3'—Hc_3' | 109.4 (10) | C_3''—O_3''—Ho_3'' | 112.0 (10) |
| C_3'—C_4'—C_5' | 108.7 (5) | C_4''—O_4''—Ho_4'' | 112.1 (13) |
| C_3'—C_4'—O_4' | 110.5 (6) | C_6''—O_6''—Ho_6'' | 109.9 (12) |
| C_3'—C_4'—Hc_4' | 106.8 (9) | H_w21—O_w2—H_w22 | 105 (2) |
| C_5'—C_4'—O_4' | 112.2 (6) | O_w2—H_w21—H_w22 | 34.0 (12) |
| C_5'—C_4'—Hc_4' | 112.1 (9) | O_w2—H_w22—H_w21 | 40.7 (13) |
| O_4'—C_4'—Hc_4' | 106.5 (10) | H_w31—O_w3—H_w32 | 113 (2) |
| C_4'—C_5'—C_6' | 114.0 (5) | O_w3—H_w31—H_w32 | 37.4 (14) |
| C_4'—C_5'—O_5' | 110.1 (6) | O_w3—H_w32—H_w31 | 30.1 (12) |
| C_4'—C_5'—Hc_5' | 107.6 (9) | H_w61—O_w6—H_w62 | 112 (2) |
| C_6'—C_5'—O_5' | 107.3 (6) | O_w6—H_w61—H_w62 | 33.3 (12) |
| C_6'—C_5'—Hc_5' | 107.4 (9) | O_w6—H_w62—H_w61 | 34.8 (13) |
| O_5'—C_5'—Hc_5' | 110.4 (9) | H_w51—O_w5—H_w52 | 110 (4) |
| C_5'—C_6'—O_6' | 112.6 (7) | O_w5—H_w51—H_w52 | 40 (2) |
| C_5'—C_6'—Hc_6' | 109.6 (9) | O_w5—H_w52—H_w51 | 30.0 (18) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| C_1—Hc_1···O_2′i | 1.087 (11) | 2.725 (15) | 3.627 (11) | 140.2 (9) |
| C_1—Hc_1···O_w2ii | 1.087 (11) | 2.916 (19) | 3.587 (14) | 120.2 (10) |
| C_3—Hc_3···O_w5 | 1.093 (15) | 2.71 (2) | 3.782 (17) | 165.7 (10) |
| C_5—Hc_5···O_3′′ | 1.115 (13) | 2.365 (14) | 3.390 (11) | 152.1 (8) |
| C_6—H′c_6···O_2iii | 1.104 (16) | 2.961 (18) | 3.793 (12) | 132.3 (10) |
| C_6—Hc_6···O_1′′iv | 1.088 (15) | 2.597 (18) | 3.404 (12) | 130.4 (11) |
| C_1′—Hc_1′···O_2iii | 1.121 (15) | 2.381 (16) | 3.480 (11) | 166.2 (11) |
| C_1′—Hc_1′···O_3iii | 1.121 (15) | 2.694 (16) | 3.428 (12) | 122.4 (9) |
| C_2′—Hc_2′···O_6′v | 1.081 (19) | 2.566 (18) | 3.434 (11) | 136.7 (10) |
| C_2′—Hc_2′···O_6′′vi | 1.081 (19) | 2.748 (18) | 3.544 (13) | 130.2 (11) |
| C_3′—Hc_3′···O_w6 | 1.111 (17) | 2.983 (17) | 3.732 (13) | 124.9 (9) |
| C_4′—Hc_4′···O_3v | 1.127 (18) | 2.683 (14) | 3.499 (9) | 128.6 (11) |
| C_5′—Hc_5′···O_4′vii | 1.099 (18) | 2.919 (17) | 3.683 (12) | 126.7 (9) |
| C_1′′—Hc_1′′···O_w5 | 1.090 (15) | 2.757 (17) | 3.643 (14) | 138.3 (11) |
| C_1′′—Hc_2′′···O_w5viii | 1.095 (18) | 2.80 (2) | 3.679 (16) | 137.2 (11) |
| C_3′′—Hc_3′′···O_4ix | 1.132 (13) | 2.794 (18) | 3.587 (11) | 126.7 (11) |
| C_4′′—Hc_4′′···C_5 | 1.074 (15) | 2.662 (15) | 3.595 (9) | 145.0 (12) |
| C_4′′—Hc_4′′···C_6 | 1.074 (15) | 2.846 (14) | 3.884 (9) | 162.6 (10) |
| C_4′′—Hc_4′′···O_5 | 1.074 (15) | 2.333 (16) | 3.193 (10) | 135.9 (13) |
| C_5′′—Hc_5′′···O_3′′ix | 1.082 (14) | 2.596 (15) | 3.346 (10) | 125.8 (10) |
| C_6′′—Hc_6′′···O_5 | 1.091 (17) | 2.750 (16) | 3.580 (10) | 132.6 (11) |
| C_6′′—H′c_6′′···O_w2 | 1.10 (3) | 2.71 (3) | 3.733 (17) | 154.7 (13) |
| C_6′′—H′c_6′′···O_w5ix | 1.10 (3) | 2.90 (3) | 3.855 (19) | 145.9 (13) |
| O_2—Ho_2···O_w3ii | 0.94 (2) | 1.86 (2) | 2.780 (15) | 165.2 (18) |
| O_3—Ho_3···C_1′′x | 0.993 (19) | 2.726 (16) | 3.559 (11) | 141.7 (13) |
| O_3—Ho_3···O_1′′x | 0.993 (19) | 1.776 (18) | 2.737 (13) | 162.0 (15) |
| O_4—Ho_4···C_4′vii | 0.952 (15) | 2.771 (14) | 3.692 (10) | 163.3 (13) |
| O_4—Ho_4···O_4′vii | 0.952 (15) | 1.693 (14) | 2.639 (11) | 172.7 (15) |
| O_2′—Ho_2′···O_w6 | 0.97 (2) | 1.87 (2) | 2.832 (17) | 174.6 (17) |
| O_3′—Ho_3′···O_w2i | 0.97 (2) | 2.03 (2) | 2.920 (16) | 152.4 (18) |
| O_4′—Ho_4′···C_6′v | 1.051 (19) | 2.571 (19) | 3.431 (13) | 138.7 (12) |
| O_4′—Ho_4′···O_6′v | 1.051 (19) | 1.703 (19) | 2.742 (13) | 168.9 (15) |
| O_6′—Ho_6′···C_3v | 0.977 (17) | 2.909 (15) | 3.809 (11) | 153.6 (12) |
| O_6′—Ho_6′···O_3v | 0.977 (17) | 1.787 (16) | 2.760 (12) | 173.6 (12) |
| O_1′′—Ho_1′′···O_w3ix | 0.999 (15) | 1.855 (16) | 2.817 (12) | 160.4 (15) |
| O_3′′—Ho_3′′···C_6′′iv | 1.000 (19) | 2.504 (15) | 3.181 (11) | 124.7 (11) |
| O_3′′—Ho_3′′···O_6′′iv | 1.000 (19) | 1.705 (18) | 2.661 (14) | 158.4 (13) |
| O_4′′—Ho_4′′···C_4ix | 0.966 (18) | 2.901 (15) | 3.837 (11) | 163.5 (13) |
| O_4′′—Ho_4′′···O_4ix | 0.966 (18) | 1.773 (17) | 2.734 (13) | 172.4 (14) |
| O_6′′—Ho_6′′···C_2′i | 0.96 (2) | 2.945 (19) | 3.544 (13) | 121.4 (14) |
| O_6′′—Ho_6′′···C_3′i | 0.96 (2) | 2.752 (19) | 3.601 (14) | 147.5 (15) |
| O_6′′—Ho_6′′···O_3′i | 0.96 (2) | 1.89 (2) | 2.846 (17) | 176.0 (17) |
| O_w2—H_w21···C_1iii | 0.98 (2) | 2.97 (2) | 3.587 (14) | 122.2 (15) |
| O_w2—H_w21···C_2iii | 0.98 (2) | 2.769 (18) | 3.591 (12) | 142.4 (16) |
| O_w2—H_w21···O_2iii | 0.98 (2) | 1.894 (18) | 2.849 (13) | 165.7 (17) |
| O_w2—H_w22···O_w6vi | 0.84 (2) | 2.12 (2) | 2.916 (17) | 158 (2) |
| O_w3—H_w31···O_3′xi | 0.83 (3) | 2.93 (2) | 3.499 (14) | 128 (2) |
| O_w3—H_w31···O_w5iii | 0.83 (3) | 2.03 (3) | 2.78 (2) | 149 (2) |
| O_w3—H_w32···C_4′′ | 1.00 (2) | 2.86 (2) | 3.762 (14) | 150.3 (14) |
| O_w3—H_w32···O_4′′ | 1.00 (2) | 1.93 (2) | 2.918 (14) | 166.3 (15) |
| O_w6—H_w61···C_2′i | 0.93 (2) | 2.87 (2) | 3.790 (13) | 168.4 (18) |
| O_w6—H_w61···O_2′i | 0.93 (2) | 1.84 (2) | 2.753 (16) | 165.0 (19) |
| O_w6—H_w62···C_5 | 0.90 (2) | 2.89 (2) | 3.789 (12) | 174.2 (18) |
| O_w6—H_w62···O_5 | 0.90 (2) | 2.08 (2) | 2.915 (12) | 154.2 (19) |
| O_w6—H_w62···O_6 | 0.90 (2) | 2.32 (2) | 2.955 (13) | 127.6 (18) |
| O_w5—H_w51···O_w2iv | 0.73 (3) | 2.07 (3) | 2.781 (19) | 166 (4) |
| O_w5—H_w52···C_3′′ | 0.94 (3) | 2.98 (2) | 3.854 (15) | 155.0 (19) |
| O_w5—H_w52···O_1 | 0.94 (3) | 2.61 (2) | 3.166 (16) | 118 (2) |
| O_w5—H_w52···O_3′′ | 0.94 (3) | 2.00 (3) | 2.930 (18) | 171 (2) |
| Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x−1, y, z; (iii) x+1, y, z; (iv) −x+1, y+1/2, −z+1/2; (v) x+1/2, −y+3/2, −z+1; (vi) x+1/2, −y+1/2, −z+1; (vii) x−1/2, −y+3/2, −z+1; (viii) −x, y−1/2, −z+1/2; (ix) −x+1, y−1/2, −z+1/2; (x) −x, y+1/2, −z+1/2; (xi) −x+3/2, −y+1, z−1/2. |
