organic papers
o2590
Hitachiet al. 3C10H12O50.5CH2Cl2 doi:10.1107/S1600536805022178 Acta Cryst.(2005). E61, o2590–o2592 Acta Crystallographica Section EStructure Reports
Online
ISSN 1600-5368
n
-Propyl gallate–dichloromethane (3/0.5)
Akio Hitachi,aTakashi Makino,b Shohei Iwataband Jin
Mizuguchib*
aSony Corporation, Media Format Department,
6-7-35 Kitashinagawa, Shinagawa-ku, Tokyo 141-0001, Japan, andbDepartment of Applied
Physics, Graduate School of Engineering, Yokohama National University, Tokiwadai 79-5, Hodogaya-ku, Yokohama 240-8501, Japan
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study T= 93 K
Mean(C–C) = 0.003 A˚ Disorder in solvent or counterion Rfactor = 0.045
wRfactor = 0.134
Data-to-parameter ratio = 11.0
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2005 International Union of Crystallography
Printed in Great Britain – all rights reserved
n-Propyl gallate (PG) is a charge-control agent used for toners in electrophotography, and shows pseudo-polymorphism. The title compound, 3C10H12O50.5CH2Cl2, 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.
Comment
PG is widely used as a charge-control agent (CCA) of the negative type for toners in electrophotograpy, as well as a colour former of leuco dyes. The acidic nature of PG plays an important role in these applications. The background of the present study has been set out in our previous paper (Iwataet al., 2005). Recently, we have isolated three kinds of solvated PG crystals, namely compound (I), 3PG0.5chloroform (Iwata
et al., 2005), the title compound, (II), 3PG0.5dichloromethane (this publication), and compound (III), 2PGacetonitrile (Mizuguchiet al., 2005), which follows the present publication.
Compound (II) was found to be entirely isostructural with (I). The asymmetric unit is composed of three independent PG molecules and half of a solvent molecule, as shown in Fig. 1. The solvent molecule is disordered around an inversion centre, just as in (I).
The nature of the intra- and intermolecular O—H O hydrogen-bond network and the molecular arrangement are exactly the same as found in (I) (Fig. 2). All molecules lie in the (421) plane, forming a sheet-like layered structure. Here again, the acid strength of PG required for applications as CCAs and colour formers is considerably weakened by the formation of intra- and intermolecular O—H O hydrogen bonds. Similarly, short intermolecular H H contacts of less than 2.4 A˚ are also found, as shown in Fig. 2, between atoms H12 and H12* [2.07 A˚ ; symmetry codes (x,y,z) and (x,y, 2z), respectively], H22 and H22* [2.10 A˚ ; symmetry codes (1x, 1y, 1z) and (1 +x, y, z), respectively], and H2
and H2* [2.14 A˚ ; symmetry codes (x, 1y, 1z) and (x, 1 +y, z), respectively]. This results from two intermolecular O—H O hydrogen bonds which exist on each side of the H H contact.
Experimental
PG was purchased from Kanto Chemicals Ltd. and used without further purification. Single crystals of (II) were grown from a dichloromethane solution by slow evaporation. After a week, a number of colourless transparent crystals were obtained in the form of blocks.
Crystal data
3C10H12O50.5CH2Cl2
Mr= 679.07 Triclinic,P1 a= 9.9439 (12) A˚ b= 12.8538 (16) A˚ c= 13.8410 (17) A˚
= 63.311 (10)
= 80.168 (11)
= 86.706 (11) V= 1557.0 (4) A˚3
Z= 2
Dx= 1.448 Mg m3 CuKradiation
Cell parameters from 13196 reflections
= 3.6–68.2
= 1.74 mm1 T= 93.1 K Block, colourless 0.400.400.40 mm
Data collection
Rigaku R-AXIS RAPID-F imaging-plate diffractometer
!scans
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) Tmin= 0.468,Tmax= 0.498
14448 measured reflections
5149 independent reflections 3794 reflections withF2> 2(F2)
Rint= 0.034
max= 68.2
h=11!11 k=15!15 l=16!16
Refinement
Refinement onF R[F2> 2(F2)] = 0.045 wR(F2) = 0.134
S= 1.05 5149 reflections 470 parameters
H-atom parameters not refined w= 1/[2
(Fo2) + {0.05[max(Fo2,0)
+ 2Fc2]/3}2]
(/)max< 0.001
max= 0.52 e A˚
3
min=0.51 e A˚
3
Table 1
Selected bond lengths (A˚ ).
O1—C3 1.369 (2)
O2—C4 1.369 (2)
O3—C5 1.362 (2)
O6—C13 1.373 (2)
O7—C14 1.377 (2)
O8—C15 1.366 (2)
O11—C23 1.369 (2)
O12—C24 1.373 (2)
[image:2.610.45.299.65.323.2]O13—C25 1.361 (2)
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
O1—H1O O4i
0.84 1.90 2.7260 (18) 170 O2—H2O O1 0.85 2.27 2.7187 (19) 113 O2—H2O O12ii
0.85 2.07 2.801 (2) 144
O3—H3O O2 0.91 2.34 2.749 (2) 107
O3—H3O O6iii
0.91 1.95 2.7672 (18) 149 O6—H6O O9ii
0.86 1.87 2.724 (2) 171 O7—H7O O2iii 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 O11iv
0.95 1.99 2.7866 (19) 140 O11—H11O O14v
0.87 1.87 2.736 (2) 171 O12—H12O O7vi
0.85 2.03 2.766 (2) 144 O12—H12O O11 0.85 2.28 2.7198 (19) 112 O13—H13O O1ii 0.89 1.97 2.770 (2) 149 O13—H13O O12 0.89 2.37 2.753 (2) 106
Symmetry codes: (i) x;y;zþ2; (ii) x;yþ1;zþ1; (iii)
xþ1;yþ1;zþ1; (iv) þxþ1;þy;þz; (v) x;y;zþ1; (vi)
þx1;þy;þz.
H atoms attached to O atoms were found in difference density maps and fixed during the least-squares refinement, withUiso(H) =
organic papers
Acta Cryst.(2005). E61, o2590–o2592 Hitachiet al. 3C10H12O50.5CH2Cl2
o2591
Figure 1
[image:2.610.328.530.70.259.2]The asymmetric unit of (II), showing 30% probability displacement ellipsoids. The solvent molecule is disordered around an inversion centre (occupancy 50%).
Figure 2
[image:2.610.314.567.535.708.2]1.2Ueq(O). All other H atoms were positioned geometrically and
included in a riding-model approximation, with C—H = 0.95 A˚ , and withUiso(H) = 1.2Ueq(C). The dichloromethane molecule is
disor-dered over two possible sites around an inversion centre, each with occupancy 0.5.
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refine-ment: 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).
References
Burnett, M. N. & Johnson, C. K. (1996).ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Higashi, T. (1995).ABSCOR. Rigaku Corporation, Tokyo, Japan.
Iwata, S., Hitachi, A., Makino, T. & Mizuguchi, J. (2005).Acta Cryst.E61, o2587–o2589.
Mizuguchi, J., Hitachi, A., Iwata, S. & Makino, T. (2005).Acta Cryst.E61, o2593–o2595.
Molecular Structure Corporation (2001).TEXSAN. Version 1.11. MSC, 9009 New Trails Drive, The Woodlands, TX 77381-5209, USA.
Rigaku (1998).PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Rigaku/MSC (2005).CrystalStructure. Version 3.7.0. Rigaku/MSC, 9009 New
Trails Drive, The Woodlands, TX 77381-5209, USA.
Sheldrick, G. M. (1985).SHELXS86. University of Go¨ttingen, Germany.
organic papers
supporting information
sup-1 Acta Cryst. (2005). E61, o2590–o2592
supporting information
Acta Cryst. (2005). E61, o2590–o2592 [https://doi.org/10.1107/S1600536805022178]
n
-Propyl gallate
–
dichloromethane (3/0.5)
Akio Hitachi, Takashi Makino, Shohei Iwata and Jin Mizuguchi
n-Propyl gallate–dichloromethane (3/0.5)
Crystal data
3C10H12O5·0.5CH2Cl2 Mr = 679.07
Triclinic, P1 Hall symbol: -P 1
a = 9.9439 (12) Å
b = 12.8538 (16) Å
c = 13.8410 (17) Å
α = 63.311 (10)°
β = 80.168 (11)°
γ = 86.706 (11)°
V = 1557.0 (4) Å3
Z = 2
F(000) = 714.00
Dx = 1.448 Mg m−3
Cu Kα radiation, λ = 1.54180 Å Cell parameters from 13196 reflections
θ = 3.6–68.2°
µ = 1.74 mm−1 T = 93 K Block, colourless 0.40 × 0.40 × 0.40 mm
Data collection
Rigaku R-AXIS RAPID-F imaging-plate diffractometer
Detector resolution: 10.00 pixels mm-1
48 frames, Δ ω = 15° scans Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
Tmin = 0.468, Tmax = 0.498
14448 measured reflections
5149 independent reflections 3794 reflections with F2 > 2σ(F2) Rint = 0.034
θmax = 68.2° h = −11→11
k = −15→15
l = −16→16
Refinement
Refinement on F R[F2 > 2σ(F2)] = 0.045 wR(F2) = 0.134 S = 1.05 5149 reflections 470 parameters
H-atom parameters not refined
w = 1/[σ2(F
o2) + {0.05[max(Fo2,0) + 2Fc2]/3}2]
(Δ/σ)max < 0.001
Δρmax = 0.52 e Å−3
Δρmin = −0.51 e Å−3
Special details
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)
x y z Uiso*/Ueq Occ. (<1)
supporting information
sup-2 Acta Cryst. (2005). E61, o2590–o2592
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)
supporting information
sup-3 Acta Cryst. (2005). E61, o2590–o2592
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)
U11 U22 U33 U12 U13 U23
supporting information
sup-4 Acta Cryst. (2005). E61, o2590–o2592
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)
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
supporting information
sup-5 Acta Cryst. (2005). E61, o2590–o2592
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
supporting information
sup-6 Acta Cryst. (2005). E61, o2590–o2592
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
supporting information
sup-7 Acta Cryst. (2005). E61, o2590–o2592
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)
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
supporting information
sup-8 Acta Cryst. (2005). E61, o2590–o2592
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
