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Acta Cryst. (2007). E63, m2454    [ doi:10.1107/S1600536807041864 ]

Chloridotetrakis(1-ethyl-1H-imidazole-[kappa]N3)copper(II) chloride monohydrate

F.-Q. Liu, W.-L. Liu, W. Li, R.-X. Li and G.-Y. Liu

Abstract top

The title compound, [CuCl(C5H8N2)4]Cl·H2O, consists of a discrete [CuCl(Eim)4]+ cation (Eim is 1-ethyl-1H-imidazole), one Cl- anion and one water molecule. The CuII ion adopts a distorted square-pyramidal geometry. The basal coordination positions are occupied by the N atoms of the Eim ligands and the apical position is occupied by a Cl- anion. In the crystal structure, ions and water molecules form three-dimensional hydrogen-bond networks which stabilize the structure.

Comment top

In title compound, the crystal structure consists of discrete CuCl(Eim)4+ cations, Cl− anions and water molecules. The CuII ion adopts a distorted square pyramidal geometry. The basal coordination positions are occupied by the N atoms of the Eim ligands with bond lengths ranging from 1.960 (7) to 2.075 (8) Å, and the apical position by a Cl anion [Cu—Cl = 2.730 (3) Å], while another chloride anion in the general position balances the charges. All these values agree well with two polymorphism complexes [CuCl(im)4Cl](im is 1H-imidazole) (Otieno et al., 2001; Jian et al., 2004). In the crystal, the title compound form three-dimensional hydrogen bond networks to stabilize the structure.

Related literature top

For related literature, see: Jian et al. (2004); Otieno et al. (2001).

Experimental top

The title compound was prepared by the reaction of 1-ethylimidazole (1.92 g, 20 mmol) with CuCl2·2H2O (0.68 g, 5 mmol) by means of hydrothermal synthesis in a stainless-steel reactor with Teflon liner at 383 K for 24 h. Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Refinement top

H atoms bonded to O were located in a difference map and their coordinates were refined with Uiso(H)=1.2Ueq(O). The other H atoms were positioned geometrically (C—H = 0.93 Å) and allowed to ride on their attached atoms Uiso(H) = 1.2–1.5Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2001) and local programs.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. The packing of (I), viewed down the c axis.
Chloridotetrakis(1-ethyl-1H-imidazole-κN3)copper(II) chloride monohydrate top
Crystal data top
[CuCl(C5H8N2)4]Cl·H2OF000 = 1124
Mr = 537.00Dx = 1.352 Mg m−3
Monoclinic, CcMo Kα radiation
λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 3489 reflections
a = 20.304 (4) Åθ = 2.1–26.0º
b = 8.6090 (17) ŵ = 1.06 mm−1
c = 17.364 (4) ÅT = 293 (2) K
β = 119.65 (3)ºBlock, blue
V = 2637.8 (12) Å30.20 × 0.10 × 0.10 mm
Z = 4
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		2811 independent reflections
Radiation source: fine-focus sealed tube2013 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.022
T = 293(2) Kθmax = 26.0º
thin–slice ω scansθmin = 2.3º
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −21→25
Tmin = 0.816, Tmax = 0.902k = 0→10
5104 measured reflectionsl = −21→0
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of
independent and constrained refinement
R[F2 > 2σ(F2)] = 0.056  w = 1/[σ2(Fo2) + (0.0852P)2 + 0.8132P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.140(Δ/σ)max = 0.007
S = 0.95Δρmax = 0.77 e Å−3
2811 reflectionsΔρmin = −0.48 e Å−3
302 parametersExtinction correction: SHELXTL (Sheldrick, 2001), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
6 restraintsExtinction coefficient: 0.0042 (6)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), with 212 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.09 (3)
Crystal data top
[CuCl(C5H8N2)4]Cl·H2OV = 2637.8 (12) Å3
Mr = 537.00Z = 4
Monoclinic, CcMo Kα
a = 20.304 (4) ŵ = 1.06 mm−1
b = 8.6090 (17) ÅT = 293 (2) K
c = 17.364 (4) Å0.20 × 0.10 × 0.10 mm
β = 119.65 (3)º
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		2811 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		2013 reflections with I > 2σ(I)
Tmin = 0.816, Tmax = 0.902Rint = 0.022
5104 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.056H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.140Δρmax = 0.77 e Å−3
S = 0.95Δρmin = −0.48 e Å−3
2811 reflectionsAbsolute structure: Flack (1983), with 212 Friedel pairs
302 parametersFlack parameter: 0.09 (3)
6 restraints
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.45278 (5)0.93673 (12)−0.00119 (6)0.0418 (3)
Cl10.33081 (13)0.7876 (3)−0.13405 (17)0.0541 (7)
Cl20.6087 (2)1.1185 (3)0.1607 (2)0.0711 (9)
O1W0.2390 (5)0.6153 (12)−0.3198 (5)0.074 (2)
N10.3969 (4)0.9903 (9)0.0603 (5)0.0382 (16)
N20.3177 (5)0.9711 (11)0.1131 (6)0.054 (2)
N30.4954 (4)0.7458 (8)0.0708 (5)0.0396 (17)
N40.5781 (4)0.5894 (8)0.1720 (4)0.0358 (16)
N50.5177 (4)0.9008 (10)−0.0617 (5)0.0402 (18)
N60.6119 (4)0.8808 (10)−0.0866 (6)0.050 (2)
N70.4203 (4)1.1413 (8)−0.0680 (5)0.0379 (17)
N80.4220 (4)1.3575 (8)−0.1323 (5)0.0427 (18)
C10.3511 (2)0.8971 (3)0.0729 (2)0.059 (3)
H1A0.34290.79320.05610.070*
C20.3413 (2)1.1234 (3)0.1246 (2)0.060 (3)
H2A0.32661.20360.14880.073*
C30.3899 (2)1.1316 (3)0.0935 (2)0.054 (3)
H3A0.41581.22120.09420.065*
C40.2617 (2)0.9038 (3)0.1347 (2)0.084 (4)
H4A0.26580.79150.13610.100*
H4B0.27310.93850.19320.100*
C50.1842 (2)0.948 (2)0.0704 (2)0.103 (6)
H5A0.14940.87580.07290.154*
H5B0.17820.94810.01200.154*
H5C0.17411.05060.08410.154*
C60.5594 (5)0.7375 (3)0.1456 (2)0.045 (2)
H6A0.58830.82320.17650.054*
C70.5227 (5)0.4971 (3)0.1093 (6)0.0364 (18)
H7A0.52020.38930.10920.044*
C80.4722 (5)0.5951 (3)0.0473 (6)0.040 (2)
H8A0.42820.5649−0.00360.048*
C90.6465 (5)0.5343 (3)0.2516 (2)0.052 (2)
H9A0.65680.42840.24150.063*
H9B0.68920.59770.26040.063*
C100.6412 (2)0.5384 (3)0.3314 (2)0.083 (4)
H10A0.68930.51150.38120.125*
H10B0.60350.46550.32640.125*
H10C0.62720.64100.33950.125*
C110.5895 (5)0.8847 (3)−0.0262 (2)0.047 (2)
H11A0.62220.87680.03450.056*
C120.5497 (2)0.8989 (3)−0.1665 (2)0.056 (3)
H12A0.54760.9031−0.22120.067*
C130.4905 (2)0.9099 (3)−0.1509 (2)0.054 (3)
H13A0.43990.9216−0.19390.065*
C140.6896 (2)0.8680 (3)−0.0699 (2)0.084 (4)
H14A0.68830.8400−0.12480.101*
H14B0.71480.7847−0.02780.101*
C150.7343 (2)1.0112 (3)−0.0352 (2)0.139 (8)
H15A0.78620.9907−0.01800.208*
H15B0.73111.04660.01530.208*
H15C0.71461.0898−0.08030.208*
C160.4634 (5)1.2435 (3)−0.0789 (6)0.042 (2)
H16A0.51581.2366−0.05260.051*
C170.3478 (2)1.3303 (3)−0.1580 (3)0.050 (2)
H17A0.30621.3907−0.19550.059*
C180.3478 (5)1.1944 (3)−0.1164 (6)0.046 (2)
H18A0.30511.1464−0.12060.056*
C190.4487 (7)1.4891 (3)−0.1631 (7)0.057 (3)
H19A0.50321.4987−0.12610.069*
H19B0.42571.5840−0.15720.069*
C200.4292 (2)1.4693 (3)−0.2577 (3)0.077 (4)
H20A0.45371.5490−0.27320.115*
H20B0.37531.4770−0.29550.115*
H20C0.44621.3692−0.26530.115*
H1WB0.275 (5)0.649 (18)−0.271 (4)0.11 (6)*
H1WA0.202 (4)0.587 (13)−0.314 (7)0.07 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0530 (6)0.0326 (5)0.0509 (6)0.0144 (6)0.0343 (5)0.0132 (6)
Cl10.0377 (12)0.0500 (15)0.0566 (15)0.0011 (11)0.0096 (11)−0.0051 (12)
Cl20.108 (2)0.0346 (13)0.088 (2)0.0124 (14)0.0623 (19)0.0071 (13)
O1W0.052 (5)0.105 (7)0.056 (5)−0.017 (5)0.019 (4)0.000 (5)
N10.040 (4)0.039 (4)0.045 (4)0.003 (4)0.029 (3)0.010 (4)
N20.058 (5)0.069 (6)0.053 (5)0.013 (5)0.043 (5)0.007 (5)
N30.043 (4)0.037 (4)0.037 (4)0.002 (3)0.018 (4)−0.001 (3)
N40.035 (4)0.032 (4)0.034 (4)−0.002 (3)0.012 (3)0.004 (3)
N50.041 (4)0.044 (4)0.037 (4)0.014 (4)0.021 (4)−0.001 (4)
N60.041 (4)0.053 (5)0.055 (5)0.003 (4)0.024 (4)−0.001 (4)
N70.040 (4)0.031 (4)0.047 (4)0.005 (3)0.025 (4)0.002 (3)
N80.060 (5)0.030 (4)0.042 (4)0.004 (3)0.028 (4)0.006 (3)
C10.072 (7)0.048 (6)0.073 (7)0.009 (5)0.050 (6)0.018 (5)
C20.064 (6)0.065 (7)0.054 (6)0.007 (6)0.030 (6)−0.015 (5)
C30.057 (6)0.056 (6)0.056 (6)−0.015 (5)0.033 (5)−0.025 (5)
C40.109 (11)0.079 (9)0.107 (11)0.011 (8)0.088 (10)0.024 (8)
C50.066 (9)0.161 (19)0.086 (10)−0.015 (9)0.042 (8)0.005 (10)
C60.036 (5)0.035 (5)0.057 (6)−0.002 (4)0.017 (5)−0.010 (5)
C70.040 (4)0.027 (4)0.043 (5)−0.001 (4)0.021 (4)−0.003 (4)
C80.043 (5)0.041 (5)0.028 (4)−0.015 (4)0.011 (4)−0.011 (4)
C90.041 (5)0.054 (6)0.047 (6)0.007 (4)0.012 (4)0.011 (5)
C100.062 (7)0.124 (13)0.048 (7)0.017 (8)0.016 (6)0.026 (8)
C110.032 (5)0.061 (6)0.044 (5)0.004 (4)0.017 (4)0.002 (5)
C120.075 (8)0.053 (7)0.046 (6)0.008 (5)0.036 (6)0.001 (5)
C130.062 (6)0.058 (6)0.044 (5)0.014 (5)0.029 (5)0.006 (5)
C140.081 (9)0.082 (9)0.113 (11)0.000 (7)0.066 (9)0.001 (8)
C150.085 (11)0.106 (12)0.24 (3)−0.042 (10)0.096 (15)−0.025 (17)
C160.038 (5)0.046 (5)0.044 (5)0.009 (4)0.021 (4)0.011 (4)
C170.047 (5)0.045 (6)0.052 (6)0.014 (5)0.021 (5)0.010 (5)
C180.038 (5)0.046 (5)0.057 (6)0.003 (4)0.025 (5)0.006 (5)
C190.089 (8)0.036 (5)0.070 (7)0.000 (5)0.058 (6)0.007 (5)
C200.094 (9)0.079 (9)0.080 (8)0.013 (7)0.060 (8)0.028 (7)
Geometric parameters (Å, °) top
Cu1—N11.960 (7)C5—H5A0.9600
Cu1—N31.986 (7)C5—H5B0.9600
Cu1—N72.031 (7)C5—H5C0.9600
Cu1—N52.075 (8)C6—H6A0.9300
Cu1—Cl12.730 (3)C7—C81.353 (13)
O1W—H1WB0.85 (10)C7—H7A0.9300
O1W—H1WA0.84 (10)C8—H8A0.9300
N1—C11.327 (13)C9—C101.442 (7)
N1—C31.383 (13)C9—H9A0.9700
N2—C11.348 (13)C9—H9B0.9700
N2—C21.377 (15)C10—H10A0.9600
N2—C41.480 (14)C10—H10B0.9600
N3—C61.308 (12)C10—H10C0.9600
N3—C81.372 (11)C11—H11A0.9300
N4—C61.345 (11)C12—C131.360 (6)
N4—C71.368 (11)C12—H12A0.9300
N4—C91.471 (12)C13—H13A0.9300
N5—C111.279 (11)C14—C151.472 (4)
N5—C131.366 (13)C14—H14A0.9700
N6—C111.334 (13)C14—H14B0.9700
N6—C121.346 (14)C15—H15A0.9600
N6—C141.459 (14)C15—H15B0.9600
N7—C161.318 (11)C15—H15C0.9600
N7—C181.364 (11)C16—H16A0.9300
N8—C161.326 (11)C17—C181.375 (6)
N8—C171.363 (12)C17—H17A0.9300
N8—C191.465 (12)C18—H18A0.9300
C1—H1A0.9300C19—C201.499 (17)
C2—C31.341 (6)C19—H19A0.9700
C2—H2A0.9300C19—H19B0.9700
C3—H3A0.9300C20—H20A0.9600
C4—C51.459 (7)C20—H20B0.9600
C4—H4A0.9700C20—H20C0.9600
C4—H4B0.9700
N1—Cu1—N392.4 (3)C8—C7—H7A127.1
N1—Cu1—N789.8 (3)N4—C7—H7A127.1
N3—Cu1—N7174.0 (3)C7—C8—N3109.8 (7)
N1—Cu1—N5174.3 (4)C7—C8—H8A125.1
N3—Cu1—N590.4 (3)N3—C8—H8A125.1
N7—Cu1—N587.0 (3)C10—C9—N4114.2 (9)
N1—Cu1—Cl192.5 (2)C10—C9—H9A108.7
N3—Cu1—Cl194.2 (2)N4—C9—H9A108.7
N7—Cu1—Cl191.3 (2)C10—C9—H9B108.7
N5—Cu1—Cl192.3 (2)N4—C9—H9B108.7
H1WB—O1W—H1WA111 (10)H9A—C9—H9B107.6
C1—N1—C3103.8 (8)C9—C10—H10A109.5
C1—N1—Cu1126.2 (7)C9—C10—H10B109.5
C3—N1—Cu1129.8 (6)H10A—C10—H10B109.5
C1—N2—C2107.4 (9)C9—C10—H10C109.5
C1—N2—C4126.3 (10)H10A—C10—H10C109.5
C2—N2—C4126.2 (10)H10B—C10—H10C109.5
C6—N3—C8105.7 (8)N5—C11—N6112.0 (9)
C6—N3—Cu1125.4 (6)N5—C11—H11A124.0
C8—N3—Cu1128.1 (6)N6—C11—H11A124.0
C6—N4—C7107.3 (7)N6—C12—C13105.9 (9)
C6—N4—C9127.0 (7)N6—C12—H12A127.0
C7—N4—C9125.7 (7)C13—C12—H12A127.0
C11—N5—C13106.1 (9)C12—C13—N5108.7 (9)
C11—N5—Cu1129.0 (7)C12—C13—H13A125.6
C13—N5—Cu1124.4 (6)N5—C13—H13A125.6
C11—N6—C12107.2 (8)N6—C14—C15113.9 (4)
C11—N6—C14127.0 (10)N6—C14—H14A108.8
C12—N6—C14125.7 (10)C15—C14—H14A108.8
C16—N7—C18106.2 (8)N6—C14—H14B108.8
C16—N7—Cu1127.6 (6)C15—C14—H14B108.8
C18—N7—Cu1126.1 (6)H14A—C14—H14B107.7
C16—N8—C17108.5 (8)C14—C15—H15A109.5
C16—N8—C19127.3 (8)C14—C15—H15B109.5
C17—N8—C19124.1 (8)H15A—C15—H15B109.5
N1—C1—N2111.9 (9)C14—C15—H15C109.5
N1—C1—H1A124.1H15A—C15—H15C109.5
N2—C1—H1A124.1H15B—C15—H15C109.5
C3—C2—N2105.3 (9)N7—C16—N8111.0 (8)
C3—C2—H2A127.4N7—C16—H16A124.5
N2—C2—H2A127.4N8—C16—H16A124.5
C2—C3—N1111.7 (4)N8—C17—C18105.2 (8)
C2—C3—H3A124.2N8—C17—H17A127.4
N1—C3—H3A124.2C18—C17—H17A127.4
C5—C4—N2112.1 (11)N7—C18—C17109.2 (8)
C5—C4—H4A109.2N7—C18—H18A125.4
N2—C4—H4A109.2C17—C18—H18A125.4
C5—C4—H4B109.2N8—C19—C20111.5 (9)
N2—C4—H4B109.2N8—C19—H19A109.3
H4A—C4—H4B107.9C20—C19—H19A109.3
C4—C5—H5A109.5N8—C19—H19B109.3
C4—C5—H5B109.5C20—C19—H19B109.3
H5A—C5—H5B109.5H19A—C19—H19B108.0
C4—C5—H5C109.5C19—C20—H20A109.5
H5A—C5—H5C109.5C19—C20—H20B109.5
H5B—C5—H5C109.5H20A—C20—H20B109.5
N3—C6—N4111.4 (8)C19—C20—H20C109.5
N3—C6—H6A124.3H20A—C20—H20C109.5
N4—C6—H6A124.3H20B—C20—H20C109.5
C8—C7—N4105.8 (7)
N3—Cu1—N1—C1−51.1 (9)C2—N2—C4—C574.7 (17)
N7—Cu1—N1—C1134.5 (9)C8—N3—C6—N4−0.7 (11)
Cl1—Cu1—N1—C143.2 (8)Cu1—N3—C6—N4−171.2 (6)
N3—Cu1—N1—C3134.9 (8)C7—N4—C6—N30.7 (11)
N7—Cu1—N1—C3−39.5 (8)C9—N4—C6—N3178.8 (8)
Cl1—Cu1—N1—C3−130.8 (8)C6—N4—C7—C8−0.3 (10)
N1—Cu1—N3—C6−90.4 (8)C9—N4—C7—C8−178.4 (8)
N5—Cu1—N3—C684.6 (8)N4—C7—C8—N3−0.1 (10)
Cl1—Cu1—N3—C6176.9 (7)C6—N3—C8—C70.5 (11)
N1—Cu1—N3—C8101.2 (8)Cu1—N3—C8—C7170.7 (6)
N5—Cu1—N3—C8−83.8 (8)C6—N4—C9—C1083.2 (14)
Cl1—Cu1—N3—C88.5 (8)C7—N4—C9—C10−99.0 (13)
N3—Cu1—N5—C11−55.9 (9)C13—N5—C11—N6−0.7 (12)
N7—Cu1—N5—C11118.7 (9)Cu1—N5—C11—N6−173.1 (7)
Cl1—Cu1—N5—C11−150.1 (9)C12—N6—C11—N51.4 (13)
N3—Cu1—N5—C13133.0 (8)C14—N6—C11—N5178.2 (10)
N7—Cu1—N5—C13−52.4 (8)C11—N6—C12—C13−1.4 (12)
Cl1—Cu1—N5—C1338.8 (8)C14—N6—C12—C13−178.3 (10)
N1—Cu1—N7—C16131.7 (8)N6—C12—C13—N51.0 (12)
N5—Cu1—N7—C16−43.6 (8)C11—N5—C13—C12−0.2 (12)
Cl1—Cu1—N7—C16−135.8 (8)Cu1—N5—C13—C12172.6 (7)
N1—Cu1—N7—C18−53.5 (8)C11—N6—C14—C15−74 (2)
N5—Cu1—N7—C18131.2 (8)C12—N6—C14—C15102.6 (18)
Cl1—Cu1—N7—C1839.0 (8)C18—N7—C16—N8−0.7 (11)
C3—N1—C1—N2−1.2 (12)Cu1—N7—C16—N8174.9 (6)
Cu1—N1—C1—N2−176.4 (7)C17—N8—C16—N70.3 (11)
C2—N2—C1—N12.2 (13)C19—N8—C16—N7−177.5 (8)
C4—N2—C1—N1178.0 (10)C16—N8—C17—C180.2 (11)
C1—N2—C2—C3−2.2 (12)C19—N8—C17—C18178.2 (9)
C4—N2—C2—C3−178.0 (11)C16—N7—C18—C170.9 (11)
N2—C2—C3—N11.6 (13)Cu1—N7—C18—C17−174.8 (6)
C1—N1—C3—C2−0.3 (12)N8—C17—C18—N7−0.7 (11)
Cu1—N1—C3—C2174.7 (8)C16—N8—C19—C20105.1 (12)
C1—N2—C4—C5−100.3 (16)C17—N8—C19—C20−72.4 (13)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···Cl2i0.84 (10)2.47 (11)3.206 (11)147
O1W—H1WB···Cl10.85 (10)2.39 (9)3.183 (9)156 (9)
C6—H6A···Cl20.932.613.401 (5)143
C7—H7A···Cl2ii0.932.813.595 (6)143
C9—H9B···Cl1iii0.972.723.598 (9)151
C11—H11A···O1Wiii0.932.473.361 (9)161
C19—H19B···Cl1iv0.972.773.713 (12)162
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x, y−1, z; (iii) x+1/2, −y+3/2, z+1/2; (iv) x, y+1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···Cl2i0.84 (10)2.47 (11)3.206 (11)147
O1W—H1WB···Cl10.85 (10)2.39 (9)3.183 (9)156 (9)
C6—H6A···Cl20.932.613.401 (5)143
C7—H7A···Cl2ii0.932.813.595 (6)143
C9—H9B···Cl1iii0.972.723.598 (9)151
C11—H11A···O1Wiii0.932.473.361 (9)161
C19—H19B···Cl1iv0.972.773.713 (12)162
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x, y−1, z; (iii) x+1/2, −y+3/2, z+1/2; (iv) x, y+1, z.
Acknowledgements top

This work was supported by the National Natural Science Foundation of China (grant No. 20601015) and the Natural Science Foundation of Shandong Province (Y2006B12).

references
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