n-Propyl gallate–chloro­form (3/0.5)

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 C₁₀H₁₂O₅·0.5CHCl₃, 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.

Key indicators

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](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

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Computing details

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)

Crystal data

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) Å^3

Data collection

Rigaku R-AXIS RAPID-F Imaging Plate diffractometer	4533 reflections with F^2 > 2σ(F^2)
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

Refinement on F	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.063	w = 1/[σ^2(Fo^2) + {0.05[Max(Fo^2,0) + 2Fc^2]/3}^2]
wR(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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···O4^i	2.741 (2)	H6O···H3O^iii	2.216
O1···O13^ii	2.794 (2)	H7O···O2^iii	2.007
O1···H13O^ii	2.068	H7O···H2O^iii	2.224
O2···O7^iii	2.787 (2)	H7O···H3O^iii	2.620
O2···H7O^iii	2.007	H7O···H10a^viii	2.538
O3···O6^iii	2.763 (2)	H7O···H12O^iv	2.370
O4···O1^i	2.741 (2)	H8O···O11^iv	2.015
O4···H1O^i	1.888	H8O···H11O^iv	2.301
O4···H2^i	2.588	H8O···H12O^iv	2.650
O4···H18a^i	2.769	H8a···H31^ix	2.770
O6···O3^iii	2.763 (2)	H9a···H10b^x	2.594
O6···O9^ii	2.729 (2)	H9a···H29b^ix	2.705
O6···H3O^iii	1.977	H10a···H7O^xi	2.538
O7···O2^iii	2.787 (2)	H10b···H9a^x	2.594
O7···O12^iv	2.775 (2)	H10c···H26^xi	2.209
O7···H12O^iv	2.059	H11O···O14^vi	1.853
O8···O11^iv	2.777 (2)	H11O···H8O^v	2.301
O9···O6^ii	2.729 (2)	H11O···H18b	2.549
O9···H6O^ii	1.878	H11O···H30a^v	2.610
O9···H12^ii	2.646	H12···O9^ii	2.646
O11···O8^v	2.777 (2)	H12···H12^ii	2.081
O11···O14^vi	2.742 (2)	H12O···O7^v	2.059
O11···H8O^v	2.015	H12O···H2O^ii	2.348
O11···H30a^v	2.685	H12O···H7O^v	2.370
O12···O7^v	2.775 (2)	H12O···H8O^v	2.650
O12···H2O^ii	2.087	H13O···O1^ii	2.068
O13···O1^ii	2.794 (2)	H13O···H1O^ii	2.256
O13···H1O^ii	2.772	H13O···H2O^ii	2.761
O13···H31^vii	2.171	H13O···H31^vii	2.556
O14···O11^vi	2.742 (2)	H16···H30c^ix	2.200
O14···H11O^vi	1.853	H18a···O4^i	2.769
O14···H22^vi	2.747	H18b···H11O	2.549
C25···H31^vii	2.704	H19a···H2	2.746
H1O···O4^i	1.888	H20c···H6^v	2.286
H1O···O13^ii	2.772	H20c···H28b^vi	2.682
H1O···H13O^ii	2.256	H22···O14^vi	2.747
H2···O4^i	2.588	H22···H22^vi	2.100
H2···H2^i	2.151	H26···H10c^viii	2.209
H2···H19a	2.746	H28a···H28a^ix	2.422
H2O···O12^ii	2.087	H28b···H20c^vi	2.682
H2O···H7O^iii	2.224	H29b···H9a^ix	2.705
H2O···H12O^ii	2.348	H30a···O11^iv	2.685
H2O···H13O^ii	2.761	H30a···H11O^iv	2.610
H3O···O6^iii	1.977	H30c···H16^ix	2.200
H3O···H6O^iii	2.216	H31···O13^vii	2.171
H3O···H7O^iii	2.620	H31···C25^vii	2.704
H6···H20c^iv	2.286	H31···H8a^ix	2.770
H6O···O9^ii	1.878	H31···H13O^vii	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)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O4^i	0.87	1.89	2.741 (2)	167
O2—H2O···O1	0.81	2.32	2.719 (2)	111
O2—H2O···O12^ii	0.81	2.09	2.809 (2)	148
O3—H3O···O2	0.89	2.33	2.753 (2)	109
O3—H3O···O6^iii	0.89	1.98	2.763 (2)	147
O6—H6O···O9^ii	0.85	1.88	2.729 (2)	177
O7—H7O···O2^iii	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···O11^iv	0.91	2.02	2.777 (2)	140
O11—H11O···O14^vi	0.91	1.85	2.742 (2)	166
O12—H12O···O7^v	0.86	2.06	2.775 (2)	140
O12—H12O···O11	0.86	2.27	2.726 (2)	113
O13—H13O···O1^ii	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.