n-Propyl gallate (PG) is a charge-control agent used for toners in electrophotography, and shows pseudo-polymorphism. In the asymmetric unit of the title compound, 3 C
10H
12O
5·0.5CHCl
3, there are three PG molecules and a half-molecule of chloroform, the solvent molecule being disordered over an inversion centre. There are intra- and intermolecular O—H
O hydrogen bonds, forming a two-dimensional hydrogen-bond network in the (421) plane.
Supporting information
CCDC reference: 282556
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (C-C) = 0.003 Å
- Disorder in solvent or counterion
- R factor = 0.063
- wR factor = 0.201
- Data-to-parameter ratio = 10.9
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT411_ALERT_2_B Short Inter H...H Contact H12 .. H12 .. 2.08 Ang.
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 68.17
From the CIF: _diffrn_reflns_theta_full 0.00
From the CIF: _reflns_number_total 5231
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 5758
Completeness (_total/calc) 90.85%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.91
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 3.00 Ratio
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.85
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C31
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc.
PLAT411_ALERT_2_C Short Inter H...H Contact H22 .. H22 .. 2.10 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: Crystal Structure (Rigaku/MSC, 2005).
n-Propyl gallate–chloroform (3/0.5)
top
Crystal data top
3C10H12O5·0.5CHCl3 | Z = 2 |
Mr = 696.29 | F(000) = 730.00 |
Triclinic, P1 | Dx = 1.466 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54180 Å |
a = 9.9393 (11) Å | Cell parameters from 13339 reflections |
b = 12.7780 (14) Å | θ = 3.6–68.2° |
c = 13.9890 (15) Å | µ = 2.12 mm−1 |
α = 64.306 (8)° | T = 93 K |
β = 80.219 (9)° | Block, colourless |
γ = 87.010 (9)° | 0.50 × 0.50 × 0.50 mm |
V = 1577.3 (3) Å3 | |
Data collection top
Rigaku R-AXIS RAPID-F Imaging Plate diffractometer | 4533 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.035 |
48 frames, Δ ω = 15° scans | θmax = 68.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −11→11 |
Tmin = 0.339, Tmax = 0.347 | k = −15→15 |
14658 measured reflections | l = −16→16 |
5231 independent reflections | |
Refinement top
Refinement on F | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.063 | w = 1/[σ2(Fo2) + {0.05[Max(Fo2,0) + 2Fc2]/3}2] |
wR(F2) = 0.201 | (Δ/σ)max < 0.001 |
S = 1.43 | Δρmax = 0.87 e Å−3 |
5231 reflections | Δρmin = −0.94 e Å−3 |
480 parameters | |
Special details top
Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The
weighted R-factor(wR), goodness of fit (S) and
R-factor (gt) are based on F, with F set to zero for
negative F. The threshold expression of F2 > 2.0
σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cl1 | 1.1408 (3) | 0.5484 (4) | −0.0875 (2) | 0.1291 (13) | 0.50 |
Cl2 | 0.9793 (5) | 0.3598 (2) | 0.0645 (2) | 0.1288 (13) | 0.50 |
Cl3 | 0.8783 (5) | 0.5815 (5) | −0.0011 (4) | 0.194 (2) | 0.50 |
O1 | 0.08458 (16) | 0.27972 (13) | 0.82755 (13) | 0.0252 (4) | |
O2 | 0.34361 (16) | 0.36502 (13) | 0.73867 (13) | 0.0256 (4) | |
O3 | 0.56092 (16) | 0.21786 (14) | 0.76840 (14) | 0.0284 (4) | |
O4 | 0.13913 (17) | −0.15903 (14) | 1.02873 (13) | 0.0288 (4) | |
O5 | 0.36439 (16) | −0.17856 (13) | 0.98918 (13) | 0.0243 (4) | |
O6 | 0.32743 (17) | 0.57119 (13) | 0.38703 (13) | 0.0283 (4) | |
O7 | 0.53922 (16) | 0.42192 (14) | 0.41365 (13) | 0.0260 (4) | |
O8 | 0.49535 (17) | 0.18864 (14) | 0.54702 (14) | 0.0289 (4) | |
O9 | −0.08783 (16) | 0.31275 (14) | 0.62730 (13) | 0.0277 (4) | |
O10 | 0.00357 (16) | 0.13562 (13) | 0.69061 (12) | 0.0242 (4) | |
O11 | −0.22553 (16) | 0.20837 (13) | 0.47222 (13) | 0.0247 (4) | |
O12 | −0.18067 (17) | 0.43990 (14) | 0.34408 (13) | 0.0280 (4) | |
O13 | 0.07730 (17) | 0.52391 (14) | 0.23567 (14) | 0.0333 (4) | |
O14 | 0.24447 (17) | 0.02953 (13) | 0.43625 (14) | 0.0297 (4) | |
O15 | 0.37636 (16) | 0.18756 (13) | 0.32952 (12) | 0.0237 (4) | |
C1 | 0.2790 (2) | 0.0105 (2) | 0.91908 (19) | 0.0211 (5) | |
C2 | 0.1671 (2) | 0.0835 (2) | 0.90425 (19) | 0.0219 (5) | |
C3 | 0.1878 (2) | 0.2018 (2) | 0.84568 (19) | 0.0213 (5) | |
C4 | 0.3196 (2) | 0.2485 (2) | 0.79858 (18) | 0.0204 (5) | |
C5 | 0.4309 (2) | 0.1748 (2) | 0.81245 (19) | 0.0216 (5) | |
C6 | 0.4112 (2) | 0.0564 (2) | 0.87342 (19) | 0.0218 (6) | |
C7 | 0.2519 (2) | −0.1158 (2) | 0.98466 (19) | 0.0223 (6) | |
C8 | 0.3471 (2) | −0.3029 (2) | 1.0554 (2) | 0.0248 (6) | |
C9 | 0.4877 (2) | −0.3543 (2) | 1.0518 (2) | 0.0267 (6) | |
C10 | 0.4804 (2) | −0.4833 (2) | 1.1253 (2) | 0.0366 (7) | |
C11 | 0.1510 (2) | 0.2944 (2) | 0.57745 (19) | 0.0213 (6) | |
C12 | 0.1710 (2) | 0.4131 (2) | 0.51104 (19) | 0.0220 (5) | |
C13 | 0.2997 (2) | 0.4562 (2) | 0.45594 (19) | 0.0219 (5) | |
C14 | 0.4097 (2) | 0.3823 (2) | 0.46716 (18) | 0.0208 (6) | |
C15 | 0.3897 (2) | 0.2639 (2) | 0.53420 (19) | 0.0215 (5) | |
C16 | 0.2608 (2) | 0.2200 (2) | 0.58851 (19) | 0.0213 (5) | |
C17 | 0.0107 (2) | 0.2508 (2) | 0.63328 (19) | 0.0211 (5) | |
C18 | −0.1304 (2) | 0.0842 (2) | 0.74667 (19) | 0.0242 (6) | |
C19 | −0.1127 (2) | −0.0460 (2) | 0.7987 (2) | 0.0264 (6) | |
C20 | −0.2479 (2) | −0.1107 (2) | 0.8581 (2) | 0.0330 (7) | |
C21 | 0.1425 (2) | 0.2156 (2) | 0.37109 (19) | 0.0210 (5) | |
C22 | 0.0136 (2) | 0.1713 (2) | 0.4281 (2) | 0.0231 (6) | |
C23 | −0.0953 (2) | 0.2452 (2) | 0.41929 (19) | 0.0207 (5) | |
C24 | −0.0760 (2) | 0.3634 (2) | 0.35496 (19) | 0.0215 (6) | |
C25 | 0.0538 (2) | 0.4079 (2) | 0.29957 (19) | 0.0225 (6) | |
C26 | 0.1623 (2) | 0.3337 (2) | 0.3061 (2) | 0.0226 (6) | |
C27 | 0.2574 (2) | 0.1345 (2) | 0.3831 (2) | 0.0236 (6) | |
C28 | 0.4958 (2) | 0.1153 (2) | 0.3377 (2) | 0.0247 (6) | |
C29 | 0.6160 (2) | 0.1938 (2) | 0.2677 (2) | 0.0260 (6) | |
C30 | 0.7459 (2) | 0.1251 (2) | 0.2705 (2) | 0.0327 (7) | |
C31 | 0.9812 (6) | 0.4944 (5) | −0.0246 (4) | 0.0384 (16) | 0.50 |
H1O | 0.0065 | 0.2495 | 0.8665 | 0.027* | |
H2 | 0.0772 | 0.0518 | 0.9344 | 0.025* | |
H2O | 0.2738 | 0.4017 | 0.7322 | 0.028* | |
H3O | 0.5611 | 0.2915 | 0.7201 | 0.030* | |
H6 | 0.4870 | 0.0065 | 0.8839 | 0.026* | |
H6O | 0.2520 | 0.6064 | 0.3808 | 0.030* | |
H7O | 0.5368 | 0.5001 | 0.3704 | 0.028* | |
H8O | 0.5760 | 0.2294 | 0.5201 | 0.032* | |
H8a | 0.2888 | −0.3358 | 1.0279 | 0.028* | |
H8b | 0.3093 | −0.3179 | 1.1273 | 0.028* | |
H9a | 0.5222 | −0.3427 | 0.9802 | 0.031* | |
H9b | 0.5467 | −0.3164 | 1.0743 | 0.031* | |
H10a | 0.4928 | −0.4950 | 1.1951 | 0.043* | |
H10b | 0.5496 | −0.5220 | 1.0980 | 0.043* | |
H10c | 0.3933 | −0.5136 | 1.1292 | 0.043* | |
H11O | −0.2257 | 0.1302 | 0.5117 | 0.026* | |
H12 | 0.0964 | 0.4641 | 0.5042 | 0.026* | |
H12O | −0.2524 | 0.4037 | 0.3890 | 0.030* | |
H13O | 0.0038 | 0.5618 | 0.2493 | 0.035* | |
H16 | 0.2473 | 0.1393 | 0.6338 | 0.024* | |
H18a | −0.1630 | 0.1104 | 0.8002 | 0.027* | |
H18b | −0.1932 | 0.1039 | 0.6977 | 0.027* | |
H19a | −0.0511 | −0.0644 | 0.8485 | 0.031* | |
H19b | −0.0762 | −0.0703 | 0.7444 | 0.031* | |
H20a | −0.2618 | −0.1203 | 0.9304 | 0.040* | |
H20b | −0.2475 | −0.1846 | 0.8573 | 0.040* | |
H20c | −0.3195 | −0.0662 | 0.8232 | 0.041* | |
H22 | 0.0006 | 0.0905 | 0.4734 | 0.026* | |
H26 | 0.2505 | 0.3637 | 0.2673 | 0.026* | |
H28a | 0.5109 | 0.0783 | 0.4102 | 0.028* | |
H28b | 0.4836 | 0.0581 | 0.3135 | 0.028* | |
H29a | 0.6275 | 0.2502 | 0.2931 | 0.030* | |
H29b | 0.5985 | 0.2318 | 0.1959 | 0.030* | |
H30a | 0.7895 | 0.1212 | 0.3273 | 0.041* | |
H30b | 0.8060 | 0.1616 | 0.2041 | 0.041* | |
H30c | 0.7228 | 0.0488 | 0.2822 | 0.040* | |
H31 | 0.9380 | 0.4802 | −0.0844 | 0.042* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0859 (18) | 0.241 (4) | 0.0599 (14) | −0.105 (2) | 0.0179 (12) | −0.064 (2) |
Cl2 | 0.206 (4) | 0.0555 (14) | 0.105 (2) | −0.044 (2) | −0.085 (2) | 0.0107 (14) |
Cl3 | 0.195 (4) | 0.272 (6) | 0.258 (5) | 0.190 (4) | −0.155 (4) | −0.225 (5) |
O1 | 0.0156 (7) | 0.0200 (8) | 0.0306 (9) | 0.0020 (6) | 0.0004 (7) | −0.0038 (7) |
O2 | 0.0159 (7) | 0.0189 (8) | 0.0343 (10) | 0.0006 (6) | −0.0020 (7) | −0.0051 (7) |
O3 | 0.0171 (8) | 0.0186 (9) | 0.0378 (10) | −0.0037 (6) | 0.0013 (7) | −0.0029 (8) |
O4 | 0.0203 (8) | 0.0226 (9) | 0.0345 (10) | −0.0031 (7) | 0.0040 (7) | −0.0065 (8) |
O5 | 0.0202 (8) | 0.0187 (8) | 0.0290 (9) | 0.0011 (6) | −0.0013 (7) | −0.0067 (7) |
O6 | 0.0180 (8) | 0.0182 (9) | 0.0376 (10) | 0.0018 (6) | −0.0010 (7) | −0.0032 (8) |
O7 | 0.0171 (7) | 0.0200 (9) | 0.0314 (9) | 0.0006 (6) | 0.0005 (7) | −0.0039 (7) |
O8 | 0.0203 (8) | 0.0202 (9) | 0.0381 (10) | 0.0040 (7) | −0.0015 (7) | −0.0067 (8) |
O9 | 0.0195 (8) | 0.0245 (9) | 0.0331 (9) | 0.0029 (7) | −0.0008 (7) | −0.0084 (8) |
O10 | 0.0179 (8) | 0.0216 (9) | 0.0279 (9) | −0.0009 (6) | 0.0003 (6) | −0.0072 (7) |
O11 | 0.0170 (7) | 0.0172 (8) | 0.0305 (9) | −0.0023 (6) | 0.0021 (6) | −0.0036 (7) |
O12 | 0.0182 (8) | 0.0194 (9) | 0.0371 (10) | 0.0031 (6) | 0.0008 (7) | −0.0059 (8) |
O13 | 0.0209 (8) | 0.0179 (9) | 0.0465 (11) | 0.0006 (7) | 0.0042 (8) | −0.0040 (8) |
O14 | 0.0228 (8) | 0.0162 (9) | 0.0388 (10) | 0.0008 (7) | 0.0017 (7) | −0.0037 (8) |
O15 | 0.0159 (8) | 0.0192 (8) | 0.0290 (9) | 0.0019 (6) | 0.0007 (6) | −0.0056 (7) |
C1 | 0.0201 (11) | 0.0223 (12) | 0.0220 (11) | 0.0023 (9) | −0.0032 (9) | −0.0109 (10) |
C2 | 0.0178 (10) | 0.0205 (12) | 0.0234 (12) | −0.0010 (9) | −0.0019 (9) | −0.0062 (10) |
C3 | 0.0193 (11) | 0.0212 (12) | 0.0222 (11) | 0.0019 (9) | −0.0031 (9) | −0.0084 (10) |
C4 | 0.0212 (11) | 0.0157 (11) | 0.0210 (12) | 0.0004 (9) | −0.0038 (9) | −0.0046 (10) |
C5 | 0.0161 (10) | 0.0232 (12) | 0.0232 (12) | −0.0016 (9) | −0.0002 (9) | −0.0086 (11) |
C6 | 0.0185 (10) | 0.0216 (12) | 0.0252 (12) | 0.0042 (9) | −0.0038 (9) | −0.0103 (10) |
C7 | 0.0213 (11) | 0.0220 (12) | 0.0223 (12) | 0.0017 (10) | −0.0031 (10) | −0.0088 (11) |
C8 | 0.0250 (12) | 0.0168 (12) | 0.0273 (13) | −0.0022 (9) | −0.0026 (10) | −0.0048 (10) |
C9 | 0.0267 (12) | 0.0225 (12) | 0.0279 (13) | 0.0013 (10) | −0.0043 (10) | −0.0081 (11) |
C10 | 0.0408 (15) | 0.0243 (14) | 0.0406 (16) | 0.0056 (12) | −0.0091 (12) | −0.0099 (13) |
C11 | 0.0201 (11) | 0.0201 (12) | 0.0228 (12) | 0.0013 (9) | −0.0044 (9) | −0.0081 (10) |
C12 | 0.0177 (10) | 0.0215 (12) | 0.0261 (12) | 0.0060 (9) | −0.0050 (9) | −0.0095 (10) |
C13 | 0.0207 (11) | 0.0184 (12) | 0.0230 (12) | −0.0003 (9) | −0.0034 (9) | −0.0056 (10) |
C14 | 0.0177 (11) | 0.0219 (12) | 0.0200 (12) | −0.0006 (9) | 0.0002 (9) | −0.0077 (10) |
C15 | 0.0197 (10) | 0.0196 (12) | 0.0223 (12) | 0.0015 (9) | −0.0017 (9) | −0.0071 (10) |
C16 | 0.0228 (11) | 0.0159 (11) | 0.0212 (12) | 0.0001 (9) | −0.0018 (9) | −0.0049 (10) |
C17 | 0.0213 (11) | 0.0201 (11) | 0.0206 (11) | 0.0018 (9) | −0.0038 (9) | −0.0077 (10) |
C18 | 0.0199 (11) | 0.0252 (12) | 0.0232 (12) | −0.0040 (9) | 0.0014 (9) | −0.0077 (11) |
C19 | 0.0201 (11) | 0.0254 (13) | 0.0316 (13) | −0.0004 (9) | −0.0012 (10) | −0.0113 (11) |
C20 | 0.0269 (13) | 0.0319 (14) | 0.0407 (15) | −0.0010 (11) | −0.0019 (11) | −0.0173 (13) |
C21 | 0.0182 (11) | 0.0187 (12) | 0.0248 (12) | 0.0028 (9) | −0.0033 (9) | −0.0085 (10) |
C22 | 0.0220 (11) | 0.0167 (11) | 0.0265 (12) | −0.0000 (9) | −0.0026 (9) | −0.0059 (10) |
C23 | 0.0201 (11) | 0.0188 (12) | 0.0221 (11) | 0.0010 (9) | −0.0023 (9) | −0.0084 (10) |
C24 | 0.0214 (11) | 0.0195 (12) | 0.0229 (12) | 0.0038 (9) | −0.0039 (9) | −0.0087 (10) |
C25 | 0.0235 (11) | 0.0157 (11) | 0.0249 (12) | 0.0013 (9) | −0.0029 (9) | −0.0062 (10) |
C26 | 0.0180 (11) | 0.0220 (12) | 0.0256 (12) | −0.0010 (9) | −0.0011 (9) | −0.0090 (11) |
C27 | 0.0217 (11) | 0.0210 (13) | 0.0261 (13) | −0.0006 (10) | −0.0007 (10) | −0.0093 (11) |
C28 | 0.0196 (11) | 0.0223 (12) | 0.0277 (12) | 0.0045 (9) | −0.0017 (9) | −0.0078 (10) |
C29 | 0.0212 (11) | 0.0257 (13) | 0.0288 (13) | 0.0028 (10) | −0.0041 (10) | −0.0098 (11) |
C30 | 0.0230 (12) | 0.0345 (15) | 0.0417 (16) | 0.0044 (11) | −0.0027 (11) | −0.0188 (13) |
C31 | 0.034 (3) | 0.039 (3) | 0.032 (3) | −0.008 (2) | 0.001 (2) | −0.007 (2) |
Geometric parameters (Å, º) top
Cl1—C31 | 1.697 (6) | C9—H9a | 0.950 |
Cl2—C31 | 1.627 (5) | C9—H9b | 0.950 |
Cl3—C31 | 1.574 (9) | C10—H10a | 0.950 |
O1—C3 | 1.367 (2) | C10—H10b | 0.950 |
O1—H1O | 0.868 | C10—H10c | 0.950 |
O2—C4 | 1.365 (2) | C11—C12 | 1.397 (3) |
O2—H2O | 0.813 | C11—C16 | 1.393 (3) |
O3—C5 | 1.364 (2) | C11—C17 | 1.482 (3) |
O3—H3O | 0.889 | C12—C13 | 1.379 (3) |
O4—C7 | 1.215 (2) | C12—H12 | 0.950 |
O5—C7 | 1.336 (2) | C13—C14 | 1.390 (3) |
O5—C8 | 1.452 (2) | C14—C15 | 1.395 (3) |
O6—C13 | 1.374 (2) | C15—C16 | 1.381 (3) |
O6—H6O | 0.851 | C16—H16 | 0.950 |
O7—C14 | 1.373 (2) | C18—C19 | 1.514 (3) |
O7—H7O | 0.918 | C18—H18a | 0.950 |
O8—C15 | 1.367 (2) | C18—H18b | 0.950 |
O8—H8O | 0.909 | C19—C20 | 1.524 (3) |
O9—C17 | 1.217 (2) | C19—H19a | 0.950 |
O10—C17 | 1.335 (2) | C19—H19b | 0.950 |
O10—C18 | 1.452 (2) | C20—H20a | 0.950 |
O11—C23 | 1.372 (2) | C20—H20b | 0.950 |
O11—H11O | 0.908 | C20—H20c | 0.950 |
O12—C24 | 1.371 (2) | C21—C22 | 1.391 (3) |
O12—H12O | 0.864 | C21—C26 | 1.387 (3) |
O13—C25 | 1.366 (2) | C21—C27 | 1.482 (3) |
O13—H13O | 0.895 | C22—C23 | 1.384 (3) |
O14—C27 | 1.220 (2) | C22—H22 | 0.950 |
O15—C27 | 1.327 (2) | C23—C24 | 1.385 (3) |
O15—C28 | 1.455 (2) | C24—C25 | 1.393 (3) |
C1—C2 | 1.397 (3) | C25—C26 | 1.387 (3) |
C1—C6 | 1.396 (3) | C26—H26 | 0.950 |
C1—C7 | 1.482 (3) | C28—C29 | 1.506 (3) |
C2—C3 | 1.378 (3) | C28—H28a | 0.950 |
C2—H2 | 0.950 | C28—H28b | 0.950 |
C3—C4 | 1.398 (3) | C29—C30 | 1.520 (3) |
C4—C5 | 1.398 (3) | C29—H29a | 0.950 |
C5—C6 | 1.383 (3) | C29—H29b | 0.950 |
C6—H6 | 0.950 | C30—H30a | 0.950 |
C8—C9 | 1.515 (3) | C30—H30b | 0.950 |
C8—H8a | 0.950 | C30—H30c | 0.950 |
C8—H8b | 0.950 | C31—H31 | 1.086 |
C9—C10 | 1.516 (3) | | |
| | | |
O1···O4i | 2.741 (2) | H6O···H3Oiii | 2.216 |
O1···O13ii | 2.794 (2) | H7O···O2iii | 2.007 |
O1···H13Oii | 2.068 | H7O···H2Oiii | 2.224 |
O2···O7iii | 2.787 (2) | H7O···H3Oiii | 2.620 |
O2···H7Oiii | 2.007 | H7O···H10aviii | 2.538 |
O3···O6iii | 2.763 (2) | H7O···H12Oiv | 2.370 |
O4···O1i | 2.741 (2) | H8O···O11iv | 2.015 |
O4···H1Oi | 1.888 | H8O···H11Oiv | 2.301 |
O4···H2i | 2.588 | H8O···H12Oiv | 2.650 |
O4···H18ai | 2.769 | H8a···H31ix | 2.770 |
O6···O3iii | 2.763 (2) | H9a···H10bx | 2.594 |
O6···O9ii | 2.729 (2) | H9a···H29bix | 2.705 |
O6···H3Oiii | 1.977 | H10a···H7Oxi | 2.538 |
O7···O2iii | 2.787 (2) | H10b···H9ax | 2.594 |
O7···O12iv | 2.775 (2) | H10c···H26xi | 2.209 |
O7···H12Oiv | 2.059 | H11O···O14vi | 1.853 |
O8···O11iv | 2.777 (2) | H11O···H8Ov | 2.301 |
O9···O6ii | 2.729 (2) | H11O···H18b | 2.549 |
O9···H6Oii | 1.878 | H11O···H30av | 2.610 |
O9···H12ii | 2.646 | H12···O9ii | 2.646 |
O11···O8v | 2.777 (2) | H12···H12ii | 2.081 |
O11···O14vi | 2.742 (2) | H12O···O7v | 2.059 |
O11···H8Ov | 2.015 | H12O···H2Oii | 2.348 |
O11···H30av | 2.685 | H12O···H7Ov | 2.370 |
O12···O7v | 2.775 (2) | H12O···H8Ov | 2.650 |
O12···H2Oii | 2.087 | H13O···O1ii | 2.068 |
O13···O1ii | 2.794 (2) | H13O···H1Oii | 2.256 |
O13···H1Oii | 2.772 | H13O···H2Oii | 2.761 |
O13···H31vii | 2.171 | H13O···H31vii | 2.556 |
O14···O11vi | 2.742 (2) | H16···H30cix | 2.200 |
O14···H11Ovi | 1.853 | H18a···O4i | 2.769 |
O14···H22vi | 2.747 | H18b···H11O | 2.549 |
C25···H31vii | 2.704 | H19a···H2 | 2.746 |
H1O···O4i | 1.888 | H20c···H6v | 2.286 |
H1O···O13ii | 2.772 | H20c···H28bvi | 2.682 |
H1O···H13Oii | 2.256 | H22···O14vi | 2.747 |
H2···O4i | 2.588 | H22···H22vi | 2.100 |
H2···H2i | 2.151 | H26···H10cviii | 2.209 |
H2···H19a | 2.746 | H28a···H28aix | 2.422 |
H2O···O12ii | 2.087 | H28b···H20cvi | 2.682 |
H2O···H7Oiii | 2.224 | H29b···H9aix | 2.705 |
H2O···H12Oii | 2.348 | H30a···O11iv | 2.685 |
H2O···H13Oii | 2.761 | H30a···H11Oiv | 2.610 |
H3O···O6iii | 1.977 | H30c···H16ix | 2.200 |
H3O···H6Oiii | 2.216 | H31···O13vii | 2.171 |
H3O···H7Oiii | 2.620 | H31···C25vii | 2.704 |
H6···H20civ | 2.286 | H31···H8aix | 2.770 |
H6O···O9ii | 1.878 | H31···H13Ovii | 2.556 |
| | | |
C3—O1—H1O | 113.3 | O6—C13—C14 | 116.21 (18) |
C4—O2—H2O | 112.6 | C12—C13—C14 | 120.40 (19) |
C5—O3—H3O | 111.2 | O7—C14—C13 | 122.09 (19) |
C7—O5—C8 | 116.44 (16) | O7—C14—C15 | 118.1 (2) |
C13—O6—H6O | 108.1 | C13—C14—C15 | 119.81 (19) |
C14—O7—H7O | 108.9 | O8—C15—C14 | 121.45 (19) |
C15—O8—H8O | 109.6 | O8—C15—C16 | 118.44 (19) |
C17—O10—C18 | 116.84 (17) | C14—C15—C16 | 120.1 (2) |
C23—O11—H11O | 108.4 | C11—C16—C15 | 119.9 (2) |
C24—O12—H12O | 109.0 | O9—C17—O10 | 123.37 (19) |
C25—O13—H13O | 108.1 | O9—C17—C11 | 123.99 (19) |
C27—O15—C28 | 117.19 (17) | O10—C17—C11 | 112.64 (19) |
C2—C1—C6 | 120.4 (2) | O10—C18—C19 | 106.52 (18) |
C2—C1—C7 | 117.72 (19) | C18—C19—C20 | 111.6 (2) |
C6—C1—C7 | 121.9 (2) | C22—C21—C26 | 120.2 (2) |
C1—C2—C3 | 119.7 (2) | C22—C21—C27 | 118.63 (19) |
O1—C3—C2 | 123.72 (19) | C26—C21—C27 | 121.19 (19) |
O1—C3—C4 | 116.01 (19) | C21—C22—C23 | 119.8 (2) |
C2—C3—C4 | 120.2 (2) | O11—C23—C22 | 123.44 (19) |
O2—C4—C3 | 121.9 (2) | O11—C23—C24 | 116.3 (2) |
O2—C4—C5 | 118.39 (18) | C22—C23—C24 | 120.26 (19) |
C3—C4—C5 | 119.8 (2) | O12—C24—C23 | 122.26 (19) |
O3—C5—C4 | 121.1 (2) | O12—C24—C25 | 117.95 (18) |
O3—C5—C6 | 118.6 (2) | C23—C24—C25 | 119.8 (2) |
C4—C5—C6 | 120.2 (2) | O13—C25—C24 | 121.6 (2) |
C1—C6—C5 | 119.6 (2) | O13—C25—C26 | 118.27 (19) |
O4—C7—O5 | 122.9 (2) | C24—C25—C26 | 120.1 (2) |
O4—C7—C1 | 124.0 (2) | C21—C26—C25 | 119.8 (2) |
O5—C7—C1 | 113.07 (18) | O14—C27—O15 | 123.2 (2) |
O5—C8—C9 | 106.91 (17) | O14—C27—C21 | 123.7 (2) |
C8—C9—C10 | 110.41 (19) | O15—C27—C21 | 113.11 (18) |
C12—C11—C16 | 120.03 (19) | O15—C28—C29 | 107.28 (17) |
C12—C11—C17 | 118.2 (2) | C28—C29—C30 | 110.94 (19) |
C16—C11—C17 | 121.73 (19) | Cl1—C31—Cl2 | 113.2 (4) |
C11—C12—C13 | 119.7 (2) | Cl1—C31—Cl3 | 116.0 (4) |
O6—C13—C12 | 123.4 (2) | Cl2—C31—Cl3 | 119.4 (4) |
Symmetry codes: (i) −x, −y, −z+2; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+1; (iv) x+1, y, z; (v) x−1, y, z; (vi) −x, −y, −z+1; (vii) −x+1, −y+1, −z; (viii) x, y+1, z−1; (ix) −x+1, −y, −z+1; (x) −x+1, −y−1, −z+2; (xi) x, y−1, z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O4i | 0.87 | 1.89 | 2.741 (2) | 167 |
O2—H2O···O1 | 0.81 | 2.32 | 2.719 (2) | 111 |
O2—H2O···O12ii | 0.81 | 2.09 | 2.809 (2) | 148 |
O3—H3O···O2 | 0.89 | 2.33 | 2.753 (2) | 109 |
O3—H3O···O6iii | 0.89 | 1.98 | 2.763 (2) | 147 |
O6—H6O···O9ii | 0.85 | 1.88 | 2.729 (2) | 177 |
O7—H7O···O2iii | 0.92 | 2.01 | 2.787 (2) | 142 |
O7—H7O···O6 | 0.92 | 2.24 | 2.728 (2) | 112 |
O8—H8O···O7 | 0.91 | 2.31 | 2.756 (2) | 110 |
O8—H8O···O11iv | 0.91 | 2.02 | 2.777 (2) | 140 |
O11—H11O···O14vi | 0.91 | 1.85 | 2.742 (2) | 166 |
O12—H12O···O7v | 0.86 | 2.06 | 2.775 (2) | 140 |
O12—H12O···O11 | 0.86 | 2.27 | 2.726 (2) | 113 |
O13—H13O···O1ii | 0.90 | 2.07 | 2.794 (2) | 138 |
O13—H13O···O12 | 0.90 | 2.29 | 2.753 (2) | 112 |
Symmetry codes: (i) −x, −y, −z+2; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+1; (iv) x+1, y, z; (v) x−1, y, z; (vi) −x, −y, −z+1. |