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n-Propyl gallate (PG) is a charge-control agent used for toners in electrophotography, and shows pseudo-polymorphism. The title compound, 3C
10H
12O
5·0.5CH
2Cl
2, is isostructural with the corresponding chloroform solvate. The asymmetric unit is composed of three PG molecules and a half-molecule of dichloromethane, the solvent 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: 282567
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (C-C) = 0.003 Å
- Disorder in solvent or counterion
- R factor = 0.045
- wR factor = 0.134
- Data-to-parameter ratio = 11.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT411_ALERT_2_B Short Inter H...H Contact H12 .. H12 .. 2.07 Ang.
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 68.19
From the CIF: _diffrn_reflns_theta_full 68.19
From the CIF: _reflns_number_total 5149
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 5688
Completeness (_total/calc) 90.52%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.90
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 ............ 0.50 Ratio
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.89
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 H2 .. H2 .. 2.14 Ang.
PLAT411_ALERT_2_C Short Inter H...H Contact H22 .. H22 .. 2.10 Ang.
PLAT413_ALERT_2_C Short Inter XH3 .. XHn H10C .. H26 .. 2.14 Ang.
PLAT417_ALERT_2_C Short Inter D-H..H-D H1O .. H13O .. 2.14 Ang.
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
12 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
5 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: CrystalStructure (Rigaku/MSC, 2005).
n-Propyl gallate–dichloromethane (3/0.5)
top
Crystal data top
3C10H12O5·0.5CH2Cl2 | Z = 2 |
Mr = 679.07 | F(000) = 714.00 |
Triclinic, P1 | Dx = 1.448 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54180 Å |
a = 9.9439 (12) Å | Cell parameters from 13196 reflections |
b = 12.8538 (16) Å | θ = 3.6–68.2° |
c = 13.8410 (17) Å | µ = 1.74 mm−1 |
α = 63.311 (10)° | T = 93 K |
β = 80.168 (11)° | Block, colourless |
γ = 86.706 (11)° | 0.40 × 0.40 × 0.40 mm |
V = 1557.0 (4) Å3 | |
Data collection top
Rigaku R-AXIS RAPID-F imaging-plate diffractometer | 3794 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.034 |
48 frames, Δ ω = 15° scans | θmax = 68.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −11→11 |
Tmin = 0.468, Tmax = 0.498 | k = −15→15 |
14448 measured reflections | l = −16→16 |
5149 independent reflections | |
Refinement top
Refinement on F | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.045 | w = 1/[σ2(Fo2) + {0.05[max(Fo2,0) + 2Fc2]/3}2] |
wR(F2) = 0.134 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.52 e Å−3 |
5149 reflections | Δρmin = −0.51 e Å−3 |
470 parameters | |
Special details top
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
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 | 0.8591 (7) | 0.5283 (6) | 0.0305 (6) | 0.0866 (17) | 0.50 |
Cl2 | 1.1405 (5) | 0.5080 (6) | −0.0558 (5) | 0.0700 (14) | 0.50 |
O1 | 0.08701 (14) | 0.27920 (12) | 0.82921 (12) | 0.0254 (4) | |
O2 | 0.34602 (14) | 0.36449 (12) | 0.73896 (12) | 0.0255 (4) | |
O3 | 0.56254 (14) | 0.21645 (12) | 0.76867 (13) | 0.0283 (4) | |
O4 | 0.13930 (14) | −0.16191 (12) | 1.02826 (13) | 0.0296 (4) | |
O5 | 0.36488 (14) | −0.18124 (12) | 0.98902 (12) | 0.0241 (4) | |
O6 | 0.32491 (14) | 0.56947 (12) | 0.38629 (12) | 0.0298 (4) | |
O7 | 0.53794 (14) | 0.42015 (12) | 0.41545 (12) | 0.0264 (4) | |
O8 | 0.49382 (14) | 0.18531 (12) | 0.54911 (12) | 0.0275 (4) | |
O9 | −0.09060 (14) | 0.30749 (12) | 0.62875 (12) | 0.0283 (4) | |
O10 | 0.00205 (14) | 0.13039 (12) | 0.69366 (12) | 0.0244 (4) | |
O11 | −0.22580 (13) | 0.20708 (12) | 0.47446 (12) | 0.0247 (4) | |
O12 | −0.18377 (14) | 0.43894 (12) | 0.34147 (13) | 0.0291 (4) | |
O13 | 0.07185 (17) | 0.52445 (13) | 0.22611 (14) | 0.0388 (4) | |
O14 | 0.24616 (16) | 0.03049 (12) | 0.43558 (13) | 0.0299 (4) | |
O15 | 0.37563 (14) | 0.19063 (12) | 0.32638 (12) | 0.0242 (4) | |
C1 | 0.2800 (2) | 0.00841 (19) | 0.91883 (18) | 0.0210 (5) | |
C2 | 0.1688 (2) | 0.08190 (19) | 0.90421 (18) | 0.0220 (5) | |
C3 | 0.1900 (2) | 0.20065 (19) | 0.84631 (18) | 0.0211 (5) | |
C4 | 0.3213 (2) | 0.24715 (19) | 0.79924 (18) | 0.0217 (5) | |
C5 | 0.4326 (2) | 0.17348 (19) | 0.81264 (18) | 0.0224 (5) | |
C6 | 0.4123 (2) | 0.05421 (19) | 0.87331 (18) | 0.0226 (5) | |
C7 | 0.2528 (2) | −0.11835 (19) | 0.98413 (18) | 0.0218 (5) | |
C8 | 0.3478 (2) | −0.30613 (18) | 1.0561 (2) | 0.0251 (6) | |
C9 | 0.4876 (2) | −0.35709 (19) | 1.05443 (19) | 0.0259 (6) | |
C10 | 0.4815 (2) | −0.4877 (2) | 1.1288 (2) | 0.0335 (6) | |
C11 | 0.1489 (2) | 0.29025 (19) | 0.57789 (18) | 0.0219 (5) | |
C12 | 0.1684 (2) | 0.4091 (2) | 0.51106 (19) | 0.0243 (6) | |
C13 | 0.2976 (2) | 0.45360 (19) | 0.45548 (18) | 0.0227 (5) | |
C14 | 0.4076 (2) | 0.37967 (19) | 0.46809 (18) | 0.0221 (5) | |
C15 | 0.3878 (2) | 0.26041 (19) | 0.53593 (18) | 0.0222 (5) | |
C16 | 0.2589 (2) | 0.21591 (19) | 0.58966 (18) | 0.0223 (5) | |
C17 | 0.0084 (2) | 0.24613 (19) | 0.63484 (18) | 0.0216 (5) | |
C18 | −0.1309 (2) | 0.07669 (19) | 0.75161 (19) | 0.0239 (5) | |
C19 | −0.1104 (2) | −0.05350 (19) | 0.80450 (19) | 0.0256 (6) | |
C20 | −0.2439 (2) | −0.1203 (2) | 0.8652 (2) | 0.0312 (6) | |
C21 | 0.1412 (2) | 0.21652 (19) | 0.36786 (19) | 0.0225 (5) | |
C22 | 0.0132 (2) | 0.17101 (19) | 0.42819 (19) | 0.0231 (5) | |
C23 | −0.0965 (2) | 0.24399 (19) | 0.41892 (18) | 0.0212 (5) | |
C24 | −0.0784 (2) | 0.36293 (19) | 0.35113 (18) | 0.0227 (5) | |
C25 | 0.0499 (2) | 0.40835 (19) | 0.29179 (19) | 0.0249 (5) | |
C26 | 0.1592 (2) | 0.33464 (19) | 0.29965 (19) | 0.0238 (5) | |
C27 | 0.2573 (2) | 0.13575 (19) | 0.38133 (18) | 0.0225 (6) | |
C28 | 0.4971 (2) | 0.11996 (19) | 0.33408 (19) | 0.0252 (6) | |
C29 | 0.6156 (2) | 0.2019 (2) | 0.26439 (19) | 0.0252 (6) | |
C30 | 0.7485 (2) | 0.1364 (2) | 0.2644 (2) | 0.0309 (6) | |
C31 | 1.0027 (6) | 0.5872 (6) | −0.0318 (5) | 0.062 (2) | 0.50 |
H1O | 0.0121 | 0.2475 | 0.8666 | 0.030* | |
H2 | 0.0788 | 0.0502 | 0.9341 | 0.026* | |
H2O | 0.2709 | 0.4005 | 0.7354 | 0.031* | |
H3O | 0.5667 | 0.2941 | 0.7217 | 0.034* | |
H6 | 0.4880 | 0.0039 | 0.8839 | 0.027* | |
H6O | 0.2502 | 0.6054 | 0.3887 | 0.036* | |
H7O | 0.5394 | 0.4970 | 0.3784 | 0.032* | |
H8O | 0.5791 | 0.2262 | 0.5251 | 0.033* | |
H8a | 0.3072 | −0.3230 | 1.1290 | 0.028* | |
H8b | 0.2917 | −0.3375 | 1.0260 | 0.028* | |
H9a | 0.5249 | −0.3433 | 0.9817 | 0.029* | |
H9b | 0.5445 | −0.3206 | 1.0794 | 0.029* | |
H10a | 0.4687 | −0.5280 | 1.0879 | 0.040* | |
H10b | 0.5642 | −0.5112 | 1.1576 | 0.039* | |
H10c | 0.4072 | −0.5055 | 1.1874 | 0.039* | |
H11O | −0.2289 | 0.1312 | 0.5090 | 0.030* | |
H12 | 0.0933 | 0.4598 | 0.5035 | 0.029* | |
H12O | −0.2582 | 0.4016 | 0.3782 | 0.035* | |
H13O | 0.0005 | 0.5686 | 0.2298 | 0.047* | |
H16 | 0.2452 | 0.1346 | 0.6347 | 0.027* | |
H18a | −0.1641 | 0.1017 | 0.8062 | 0.027* | |
H18b | −0.1939 | 0.0967 | 0.7019 | 0.027* | |
H19a | −0.0488 | −0.0719 | 0.8551 | 0.029* | |
H19b | −0.0729 | −0.0761 | 0.7491 | 0.029* | |
H20a | −0.2856 | −0.1367 | 0.8165 | 0.038* | |
H20b | −0.2264 | −0.1913 | 0.9251 | 0.038* | |
H20c | −0.3032 | −0.0748 | 0.8916 | 0.038* | |
H22 | 0.0015 | 0.0900 | 0.4756 | 0.028* | |
H26 | 0.2465 | 0.3652 | 0.2582 | 0.029* | |
H28a | 0.5115 | 0.0804 | 0.4081 | 0.029* | |
H28b | 0.4869 | 0.0647 | 0.3077 | 0.030* | |
H29a | 0.6251 | 0.2558 | 0.2925 | 0.029* | |
H29b | 0.5979 | 0.2428 | 0.1913 | 0.029* | |
H30a | 0.7604 | 0.1153 | 0.2059 | 0.038* | |
H30b | 0.8230 | 0.1849 | 0.2551 | 0.038* | |
H30c | 0.7448 | 0.0682 | 0.3321 | 0.038* | |
H31a | 0.9882 | 0.6457 | −0.1016 | 0.074* | 0.50 |
H31b | 1.0306 | 0.6227 | 0.0089 | 0.074* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.067 (2) | 0.090 (3) | 0.111 (4) | 0.008 (2) | −0.027 (2) | −0.048 (3) |
Cl2 | 0.0304 (14) | 0.118 (4) | 0.072 (2) | −0.0226 (19) | 0.0092 (14) | −0.054 (3) |
O1 | 0.0169 (7) | 0.0190 (8) | 0.0320 (9) | 0.0015 (6) | −0.0001 (6) | −0.0057 (7) |
O2 | 0.0190 (7) | 0.0161 (8) | 0.0335 (9) | 0.0009 (6) | −0.0024 (7) | −0.0049 (7) |
O3 | 0.0158 (7) | 0.0203 (8) | 0.0390 (10) | −0.0018 (6) | 0.0015 (7) | −0.0064 (8) |
O4 | 0.0202 (8) | 0.0216 (8) | 0.0382 (10) | −0.0006 (6) | 0.0019 (7) | −0.0077 (8) |
O5 | 0.0198 (7) | 0.0164 (7) | 0.0304 (9) | 0.0005 (6) | −0.0010 (6) | −0.0066 (7) |
O6 | 0.0191 (8) | 0.0198 (8) | 0.0381 (10) | 0.0019 (6) | 0.0002 (7) | −0.0038 (7) |
O7 | 0.0178 (7) | 0.0190 (8) | 0.0329 (9) | 0.0001 (6) | 0.0006 (6) | −0.0049 (7) |
O8 | 0.0176 (7) | 0.0202 (8) | 0.0354 (9) | 0.0028 (6) | 0.0009 (6) | −0.0065 (7) |
O9 | 0.0216 (8) | 0.0244 (8) | 0.0349 (9) | 0.0038 (6) | −0.0033 (7) | −0.0106 (7) |
O10 | 0.0178 (7) | 0.0209 (8) | 0.0282 (9) | −0.0016 (6) | 0.0019 (6) | −0.0072 (7) |
O11 | 0.0177 (7) | 0.0161 (8) | 0.0324 (9) | −0.0014 (6) | 0.0027 (6) | −0.0061 (7) |
O12 | 0.0177 (7) | 0.0192 (8) | 0.0405 (10) | 0.0012 (6) | 0.0022 (7) | −0.0072 (7) |
O13 | 0.0230 (8) | 0.0168 (8) | 0.0551 (12) | 0.0033 (6) | 0.0063 (8) | −0.0020 (8) |
O14 | 0.0256 (8) | 0.0174 (8) | 0.0371 (10) | 0.0008 (7) | −0.0000 (7) | −0.0057 (7) |
O15 | 0.0171 (7) | 0.0185 (8) | 0.0303 (9) | 0.0024 (6) | 0.0001 (6) | −0.0065 (7) |
C1 | 0.0200 (10) | 0.0194 (11) | 0.0221 (11) | −0.0000 (9) | −0.0016 (9) | −0.0086 (10) |
C2 | 0.0208 (11) | 0.0206 (11) | 0.0226 (11) | −0.0010 (9) | −0.0009 (9) | −0.0087 (10) |
C3 | 0.0196 (10) | 0.0208 (11) | 0.0222 (11) | 0.0040 (9) | −0.0049 (9) | −0.0090 (10) |
C4 | 0.0251 (11) | 0.0158 (10) | 0.0222 (11) | 0.0001 (9) | −0.0051 (9) | −0.0061 (10) |
C5 | 0.0195 (10) | 0.0200 (11) | 0.0238 (12) | −0.0023 (9) | −0.0016 (9) | −0.0068 (10) |
C6 | 0.0189 (10) | 0.0219 (11) | 0.0265 (12) | 0.0025 (9) | −0.0034 (9) | −0.0107 (10) |
C7 | 0.0197 (11) | 0.0219 (12) | 0.0240 (12) | 0.0020 (9) | −0.0030 (9) | −0.0107 (10) |
C8 | 0.0241 (11) | 0.0152 (11) | 0.0307 (13) | −0.0035 (9) | −0.0018 (10) | −0.0061 (10) |
C9 | 0.0260 (11) | 0.0187 (11) | 0.0290 (13) | 0.0005 (9) | −0.0029 (10) | −0.0077 (10) |
C10 | 0.0292 (13) | 0.0251 (13) | 0.0421 (15) | 0.0030 (10) | −0.0034 (11) | −0.0124 (12) |
C11 | 0.0216 (11) | 0.0207 (11) | 0.0227 (11) | −0.0016 (9) | −0.0027 (9) | −0.0091 (10) |
C12 | 0.0204 (11) | 0.0233 (12) | 0.0273 (12) | 0.0030 (9) | −0.0031 (9) | −0.0103 (10) |
C13 | 0.0219 (11) | 0.0181 (11) | 0.0251 (12) | 0.0004 (9) | −0.0037 (9) | −0.0069 (10) |
C14 | 0.0173 (10) | 0.0233 (12) | 0.0222 (12) | −0.0034 (9) | 0.0004 (9) | −0.0080 (10) |
C15 | 0.0214 (10) | 0.0212 (11) | 0.0240 (12) | 0.0036 (9) | −0.0048 (9) | −0.0103 (10) |
C16 | 0.0240 (11) | 0.0172 (11) | 0.0218 (11) | −0.0008 (9) | −0.0021 (9) | −0.0057 (10) |
C17 | 0.0219 (11) | 0.0214 (11) | 0.0211 (11) | 0.0011 (9) | −0.0032 (9) | −0.0092 (10) |
C18 | 0.0170 (10) | 0.0257 (12) | 0.0254 (12) | −0.0014 (9) | 0.0017 (9) | −0.0098 (10) |
C19 | 0.0232 (11) | 0.0230 (11) | 0.0259 (12) | −0.0014 (9) | 0.0008 (9) | −0.0083 (10) |
C20 | 0.0296 (12) | 0.0273 (13) | 0.0356 (14) | −0.0027 (10) | −0.0032 (11) | −0.0133 (12) |
C21 | 0.0210 (11) | 0.0222 (11) | 0.0244 (12) | 0.0021 (9) | −0.0031 (9) | −0.0110 (10) |
C22 | 0.0223 (11) | 0.0174 (11) | 0.0268 (12) | 0.0004 (9) | −0.0027 (9) | −0.0078 (10) |
C23 | 0.0189 (10) | 0.0210 (11) | 0.0215 (11) | −0.0015 (9) | 0.0003 (9) | −0.0085 (10) |
C24 | 0.0194 (10) | 0.0210 (11) | 0.0275 (12) | 0.0042 (9) | −0.0034 (9) | −0.0113 (10) |
C25 | 0.0231 (11) | 0.0154 (11) | 0.0287 (13) | −0.0025 (9) | 0.0008 (10) | −0.0048 (10) |
C26 | 0.0199 (10) | 0.0209 (11) | 0.0267 (12) | −0.0019 (9) | 0.0009 (9) | −0.0086 (10) |
C27 | 0.0224 (11) | 0.0203 (12) | 0.0238 (12) | 0.0011 (9) | −0.0029 (9) | −0.0092 (10) |
C28 | 0.0223 (11) | 0.0191 (11) | 0.0319 (13) | 0.0081 (9) | −0.0070 (10) | −0.0094 (10) |
C29 | 0.0230 (11) | 0.0230 (11) | 0.0268 (12) | 0.0037 (9) | −0.0039 (9) | −0.0090 (10) |
C30 | 0.0235 (11) | 0.0318 (13) | 0.0381 (14) | 0.0037 (10) | −0.0056 (10) | −0.0164 (12) |
C31 | 0.040 (3) | 0.085 (5) | 0.069 (4) | −0.007 (3) | 0.003 (3) | −0.045 (4) |
Geometric parameters (Å, º) top
Cl1—Cl2i | 0.440 (8) | C9—C10 | 1.523 (2) |
Cl1—C31 | 1.572 (9) | C9—H9a | 0.950 |
Cl1—C31i | 1.961 (10) | C9—H9b | 0.950 |
Cl2—C31 | 1.736 (10) | C10—H10a | 0.950 |
Cl2—C31i | 1.808 (8) | C10—H10b | 0.950 |
O1—C3 | 1.369 (2) | C10—H10c | 0.950 |
O1—H1O | 0.838 | C11—C12 | 1.389 (2) |
O2—C4 | 1.369 (2) | C11—C16 | 1.392 (3) |
O2—H2O | 0.852 | C11—C17 | 1.486 (2) |
O3—C5 | 1.362 (2) | C12—C13 | 1.386 (2) |
O3—H3O | 0.913 | C12—H12 | 0.950 |
O4—C7 | 1.221 (2) | C13—C14 | 1.388 (3) |
O5—C7 | 1.332 (2) | C14—C15 | 1.396 (2) |
O5—C8 | 1.451 (2) | C15—C16 | 1.378 (2) |
O6—C13 | 1.373 (2) | C16—H16 | 0.950 |
O6—H6O | 0.856 | C18—C19 | 1.513 (3) |
O7—C14 | 1.377 (2) | C18—H18a | 0.950 |
O7—H7O | 0.885 | C18—H18b | 0.950 |
O8—C15 | 1.366 (2) | C19—C20 | 1.519 (3) |
O8—H8O | 0.950 | C19—H19a | 0.950 |
O9—C17 | 1.216 (2) | C19—H19b | 0.950 |
O10—C17 | 1.336 (2) | C20—H20a | 0.950 |
O10—C18 | 1.454 (2) | C20—H20b | 0.950 |
O11—C23 | 1.369 (2) | C20—H20c | 0.950 |
O11—H11O | 0.872 | C21—C22 | 1.394 (2) |
O12—C24 | 1.373 (2) | C21—C26 | 1.384 (2) |
O12—H12O | 0.854 | C21—C27 | 1.486 (3) |
O13—C25 | 1.361 (2) | C22—C23 | 1.381 (3) |
O13—H13O | 0.892 | C22—H22 | 0.950 |
O14—C27 | 1.218 (2) | C23—C24 | 1.391 (2) |
O15—C27 | 1.330 (2) | C24—C25 | 1.392 (2) |
O15—C28 | 1.458 (2) | C25—C26 | 1.386 (3) |
C1—C2 | 1.393 (3) | C26—H26 | 0.950 |
C1—C6 | 1.395 (2) | C28—C29 | 1.507 (2) |
C1—C7 | 1.480 (2) | C28—H28a | 0.950 |
C2—C3 | 1.377 (2) | C28—H28b | 0.950 |
C2—H2 | 0.950 | C29—C30 | 1.526 (3) |
C3—C4 | 1.392 (2) | C29—H29a | 0.950 |
C4—C5 | 1.396 (3) | C29—H29b | 0.950 |
C5—C6 | 1.385 (2) | C30—H30a | 0.950 |
C6—H6 | 0.950 | C30—H30b | 0.950 |
C8—C9 | 1.504 (3) | C30—H30c | 0.950 |
C8—H8a | 0.950 | C31—H31a | 0.950 |
C8—H8b | 0.950 | C31—H31b | 0.950 |
| | | |
O1···O4ii | 2.7260 (18) | H7O···H2Oiv | 2.276 |
O1···O13iii | 2.770 (2) | H7O···H3Oiv | 2.660 |
O1···H13Oiii | 1.966 | H7O···H12Ovi | 2.296 |
O2···O7iv | 2.7879 (18) | H8O···O11vi | 1.988 |
O2···H7Oiv | 2.027 | H8O···H11Ovi | 2.240 |
O2···H9bv | 2.722 | H8O···H12Ovi | 2.649 |
O3···O6iv | 2.7672 (18) | H8a···H3Ov | 2.759 |
O4···O1ii | 2.7260 (18) | H8b···H29bix | 2.734 |
O4···H1Oii | 1.898 | H8b···H31bx | 2.743 |
O4···H2ii | 2.639 | H9a···H10axi | 2.250 |
O4···H18aii | 2.779 | H9a···H29bix | 2.633 |
O6···O3iv | 2.7672 (18) | H9b···O2v | 2.722 |
O6···O9iii | 2.724 (2) | H9b···C4v | 2.797 |
O6···H3Oiv | 1.945 | H10a···H9axi | 2.250 |
O7···O2iv | 2.7879 (18) | H10a···H10axi | 2.187 |
O7···O12vi | 2.766 (2) | H10c···H26xii | 2.142 |
O7···H12Ovi | 2.032 | H11O···O14viii | 1.871 |
O8···O11vi | 2.7866 (19) | H11O···H8Ovii | 2.240 |
O9···O6iii | 2.724 (2) | H11O···H18b | 2.584 |
O9···H6Oiii | 1.874 | H12···O9iii | 2.718 |
O9···H12iii | 2.718 | H12···H12iii | 2.066 |
O11···O8vii | 2.7866 (19) | H12O···O7vii | 2.032 |
O11···O14viii | 2.736 (2) | H12O···H2Oiii | 2.323 |
O11···H8Ovii | 1.988 | H12O···H7Ovii | 2.296 |
O12···O7vii | 2.766 (2) | H12O···H8Ovii | 2.649 |
O12···H2Oiii | 2.069 | H13O···O1iii | 1.966 |
O13···O1iii | 2.770 (2) | H13O···H1Oiii | 2.138 |
O13···H1Oiii | 2.764 | H13O···H2Oiii | 2.698 |
O13···H31bvii | 2.784 | H13O···H31bvii | 2.779 |
O14···O11viii | 2.736 (2) | H16···H30cix | 2.433 |
O14···H11Oviii | 1.871 | H18a···O4ii | 2.779 |
O14···H22viii | 2.769 | H18b···H11O | 2.584 |
O15···H20aviii | 2.665 | H19a···H2 | 2.741 |
C4···H9bv | 2.797 | H19b···H30bix | 2.785 |
C7···H30aix | 2.639 | H20a···O15viii | 2.665 |
C27···H20aviii | 2.699 | H20a···C27viii | 2.699 |
H1O···O4ii | 1.898 | H20a···H28bviii | 2.711 |
H1O···O13iii | 2.764 | H20c···H6vii | 2.255 |
H1O···H13Oiii | 2.138 | H22···O14viii | 2.769 |
H2···O4ii | 2.639 | H22···H22viii | 2.099 |
H2···H2ii | 2.143 | H26···H10cxiii | 2.142 |
H2···H19a | 2.741 | H28a···H28aix | 2.435 |
H2O···O12iii | 2.069 | H28b···H20aviii | 2.711 |
H2O···H7Oiv | 2.276 | H29b···H8bix | 2.734 |
H2O···H12Oiii | 2.323 | H29b···H9aix | 2.633 |
H2O···H13Oiii | 2.698 | H30a···C7ix | 2.639 |
H3O···O6iv | 1.945 | H30b···H19bix | 2.785 |
H3O···H6Oiv | 2.206 | H30b···H31ai | 2.781 |
H3O···H7Oiv | 2.660 | H30c···H16ix | 2.433 |
H3O···H8av | 2.759 | H31a···H30bi | 2.781 |
H6···H20cvi | 2.255 | H31b···O13vi | 2.784 |
H6O···O9iii | 1.874 | H31b···H8bxiv | 2.743 |
H6O···H3Oiv | 2.206 | H31b···H13Ovi | 2.779 |
H7O···O2iv | 2.027 | | |
| | | |
C3—O1—H1O | 111.9 | O6—C13—C12 | 123.49 (19) |
C4—O2—H2O | 109.8 | O6—C13—C14 | 116.54 (17) |
C5—O3—H3O | 113.4 | C12—C13—C14 | 119.97 (18) |
C7—O5—C8 | 116.58 (15) | O7—C14—C13 | 121.99 (17) |
C13—O6—H6O | 107.0 | O7—C14—C15 | 118.02 (18) |
C14—O7—H7O | 110.3 | C13—C14—C15 | 119.99 (18) |
C15—O8—H8O | 110.9 | O8—C15—C14 | 121.34 (17) |
C17—O10—C18 | 117.54 (16) | O8—C15—C16 | 118.62 (18) |
C23—O11—H11O | 109.3 | C14—C15—C16 | 120.0 (2) |
C24—O12—H12O | 110.2 | C11—C16—C15 | 119.95 (18) |
C25—O13—H13O | 114.7 | O9—C17—O10 | 123.22 (18) |
C27—O15—C28 | 117.51 (15) | O9—C17—C11 | 124.33 (18) |
C2—C1—C6 | 120.43 (19) | O10—C17—C11 | 112.45 (18) |
C2—C1—C7 | 117.87 (18) | O10—C18—C19 | 106.51 (17) |
C6—C1—C7 | 121.70 (19) | C18—C19—C20 | 111.69 (18) |
C1—C2—C3 | 119.73 (19) | C22—C21—C26 | 120.3 (2) |
O1—C3—C2 | 123.63 (18) | C22—C21—C27 | 118.35 (17) |
O1—C3—C4 | 116.06 (18) | C26—C21—C27 | 121.29 (18) |
C2—C3—C4 | 120.3 (2) | C21—C22—C23 | 119.84 (18) |
O2—C4—C3 | 121.97 (19) | O11—C23—C22 | 123.93 (17) |
O2—C4—C5 | 118.04 (17) | O11—C23—C24 | 116.11 (19) |
C3—C4—C5 | 119.99 (19) | C22—C23—C24 | 119.95 (18) |
O3—C5—C4 | 121.36 (18) | O12—C24—C23 | 121.89 (17) |
O3—C5—C6 | 118.67 (19) | O12—C24—C25 | 118.01 (17) |
C4—C5—C6 | 119.96 (19) | C23—C24—C25 | 120.1 (2) |
C1—C6—C5 | 119.6 (2) | O13—C25—C24 | 121.7 (2) |
O4—C7—O5 | 122.90 (19) | O13—C25—C26 | 118.45 (18) |
O4—C7—C1 | 123.91 (19) | C24—C25—C26 | 119.85 (18) |
O5—C7—C1 | 113.19 (16) | C21—C26—C25 | 119.93 (19) |
O5—C8—C9 | 106.95 (15) | O14—C27—O15 | 123.2 (2) |
C8—C9—C10 | 110.92 (17) | O14—C27—C21 | 124.09 (18) |
C12—C11—C16 | 120.17 (18) | O15—C27—C21 | 112.69 (17) |
C12—C11—C17 | 118.07 (19) | O15—C28—C29 | 106.98 (16) |
C16—C11—C17 | 121.76 (18) | C28—C29—C30 | 111.45 (18) |
C11—C12—C13 | 119.9 (2) | Cl1—C31—Cl2 | 122.0 (6) |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x, −y, −z+2; (iii) −x, −y+1, −z+1; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y, −z+2; (vi) x+1, y, z; (vii) x−1, y, z; (viii) −x, −y, −z+1; (ix) −x+1, −y, −z+1; (x) x−1, y−1, z+1; (xi) −x+1, −y−1, −z+2; (xii) x, y−1, z+1; (xiii) x, y+1, z−1; (xiv) x+1, y+1, z−1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O4ii | 0.84 | 1.90 | 2.7260 (18) | 170 |
O2—H2O···O1 | 0.85 | 2.27 | 2.7187 (19) | 113 |
O2—H2O···O12iii | 0.85 | 2.07 | 2.801 (2) | 144 |
O3—H3O···O2 | 0.91 | 2.34 | 2.749 (2) | 107 |
O3—H3O···O6iv | 0.91 | 1.95 | 2.7672 (18) | 149 |
O6—H6O···O9iii | 0.86 | 1.87 | 2.724 (2) | 171 |
O7—H7O···O2iv | 0.89 | 2.03 | 2.7879 (18) | 143 |
O7—H7O···O6 | 0.89 | 2.28 | 2.732 (2) | 111 |
O8—H8O···O7 | 0.95 | 2.32 | 2.7542 (19) | 107 |
O8—H8O···O11vi | 0.95 | 1.99 | 2.7866 (19) | 140 |
O11—H11O···O14viii | 0.87 | 1.87 | 2.736 (2) | 171 |
O12—H12O···O7vii | 0.85 | 2.03 | 2.766 (2) | 144 |
O12—H12O···O11 | 0.85 | 2.28 | 2.7198 (19) | 112 |
O13—H13O···O1iii | 0.89 | 1.97 | 2.770 (2) | 149 |
O13—H13O···O12 | 0.89 | 2.37 | 2.753 (2) | 106 |
Symmetry codes: (ii) −x, −y, −z+2; (iii) −x, −y+1, −z+1; (iv) −x+1, −y+1, −z+1; (vi) x+1, y, z; (vii) x−1, y, z; (viii) −x, −y, −z+1. |
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