Tetra-imidazole-bis(trichloro-acetato)copper(II).

The title compound, [Cu(C(2)Cl(3)O(2))(2)(C(3)H(4)N(2))(4)], was prepared by the reaction of imidazole and trichloro-acetatocopper(II). The Cu(II) atom adopts a distorted octa-hedral coordination geometry, binding the N atoms of four imidazole ligands and the carboxyl-ate O atoms of two trichloro-acetate anions. The mol-ecular structure and packing are stabilized by N-H⋯O hydrogen-bonding inter-actions. Close inter-molecular Cl⋯Cl contacts [3.498 (3) Å] are also found in the structure.

Related literature

For background to work on metal-organic frameworks, see: Chen et al. (2001 ▶); Fang et al. (2005 ▶). For a related structure, see: Moncol et al. (2007 ▶).

Experimental

Crystal data

[Cu(C2Cl3O2)2(C3H4N2)4]

M = 660.61

Triclinic,

a = 10.054 (2) Å

b = 10.539 (2) Å

c = 12.959 (3) Å

α = 108.12 (3)°

β = 92.93 (3)°

γ = 95.18 (3)°

V = 1295.2 (4) Å3

Z = 2

Mo Kα radiation

μ = 1.50 mm−1

T = 293 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

12377 measured reflections

5823 independent reflections

5048 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.168

S = 1.05

5823 reflections

316 parameters

H-atom parameters constrained

Δρmax = 1.43 e Å−3

Δρmin = −0.86 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017459/sj2779sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017459/sj2779Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C2Cl3O2)2(C3H4N2)4]	Z = 2
Mr = 660.61	F(000) = 662
Triclinic, P1	Dx = 1.694 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.054 (2) Å	Cell parameters from 2238 reflections
b = 10.539 (2) Å	θ = 2.1–26.3°
c = 12.959 (3) Å	µ = 1.50 mm−1
α = 108.12 (3)°	T = 293 K
β = 92.93 (3)°	Rod, blue
γ = 95.18 (3)°	0.22 × 0.20 × 0.18 mm
V = 1295.2 (4) Å3

Bruker SMART CCD area-detector diffractometer	5048 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
graphite	θmax = 27.5°, θmin = 3.0°
φ and ω scans	h = −13→10
12377 measured reflections	k = −13→13
5823 independent reflections	l = −16→16

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1013P)2 + 0.8989P] where P = (Fo2 + 2Fc2)/3
5823 reflections	(Δ/σ)max < 0.001
316 parameters	Δρmax = 1.43 e Å−3
0 restraints	Δρmin = −0.85 e Å−3

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

	x	y	z	Uiso*/Ueq
Cu1	0.26177 (3)	0.25376 (3)	0.24476 (3)	0.02655 (14)
Cl1	0.41741 (11)	−0.13876 (10)	0.38566 (9)	0.0542 (3)
Cl4	−0.12008 (10)	0.61045 (11)	0.09196 (10)	0.0593 (3)
Cl6	0.14287 (9)	0.67968 (9)	0.19926 (13)	0.0687 (4)
Cl2	0.44972 (12)	−0.16467 (11)	0.16082 (9)	0.0619 (3)
Cl3	0.67814 (10)	−0.15040 (9)	0.30617 (13)	0.0744 (4)
Cl5	−0.08098 (15)	0.63279 (11)	0.31833 (10)	0.0716 (4)
N7	0.2999 (2)	0.3951 (2)	0.3900 (2)	0.0290 (5)
N3	0.2209 (2)	0.1099 (2)	0.1006 (2)	0.0296 (5)
N1	0.1157 (2)	0.1667 (2)	0.3089 (2)	0.0294 (5)
O1	0.6441 (2)	0.1316 (2)	0.3576 (2)	0.0412 (6)
O3	0.1177 (2)	0.4023 (2)	0.1870 (2)	0.0390 (5)
C16	0.0052 (3)	0.4292 (3)	0.1668 (2)	0.0271 (6)
N5	0.4180 (2)	0.3358 (2)	0.1859 (2)	0.0269 (5)
C14	0.5229 (3)	−0.0894 (3)	0.2966 (3)	0.0349 (7)
N8	0.3302 (3)	0.5850 (3)	0.5243 (2)	0.0424 (7)
H8A	0.3349	0.6695	0.5591	0.051*
C15	−0.0107 (3)	0.5819 (3)	0.1915 (3)	0.0357 (7)
C4	0.1621 (3)	−0.0146 (3)	0.0788 (3)	0.0377 (7)
H4A	0.1307	−0.0507	0.1311	0.045*
C3	−0.0074 (3)	0.1991 (3)	0.3191 (3)	0.0335 (6)
H3A	−0.0390	0.2708	0.3018	0.040*
N6	0.6185 (2)	0.3773 (3)	0.1383 (2)	0.0337 (6)
H6A	0.7006	0.3686	0.1245	0.040*
O2	0.4247 (2)	0.1096 (2)	0.3115 (2)	0.0460 (6)
C12	0.2979 (4)	0.5269 (3)	0.4173 (3)	0.0394 (7)
H12A	0.2769	0.5727	0.3689	0.047*
N2	−0.0805 (3)	0.1150 (3)	0.3579 (2)	0.0376 (6)
H2A	−0.1633	0.1184	0.3713	0.045*
C13	0.5316 (3)	0.0686 (3)	0.3258 (3)	0.0294 (6)
C9	0.5368 (3)	0.2938 (3)	0.1716 (3)	0.0313 (6)
H9A	0.5608	0.2159	0.1833	0.038*
C1	0.1205 (3)	0.0559 (3)	0.3430 (3)	0.0399 (7)
H1A	0.1957	0.0112	0.3454	0.048*
N4	0.1536 (3)	−0.0808 (3)	−0.0272 (3)	0.0433 (7)
H4B	0.1195	−0.1626	−0.0581	0.052*
C8	0.5480 (3)	0.4792 (3)	0.1302 (3)	0.0424 (8)
H8B	0.5789	0.5522	0.1086	0.051*
C2	−0.0014 (3)	0.0224 (4)	0.3726 (3)	0.0438 (8)
H2B	−0.0262	−0.0491	0.3978	0.053*
C7	0.4245 (3)	0.4526 (3)	0.1596 (3)	0.0381 (7)
H7A	0.3546	0.5052	0.1618	0.046*
C11	0.3542 (4)	0.4870 (4)	0.5681 (3)	0.0456 (8)
H11A	0.3785	0.4980	0.6409	0.055*
C6	0.2081 (5)	0.0029 (5)	−0.0779 (3)	0.0653 (13)
H6B	0.2160	−0.0161	−0.1523	0.078*
C5	0.2490 (5)	0.1207 (4)	0.0017 (3)	0.0543 (10)
H5A	0.2902	0.1974	−0.0095	0.065*
C10	0.3354 (4)	0.3696 (3)	0.4845 (3)	0.0405 (7)
H10A	0.3452	0.2852	0.4904	0.049*
O4	−0.1012 (2)	0.3534 (2)	0.1345 (2)	0.0390 (6)

	U11	U22	U33	U12	U13	U23
Cu1	0.0222 (2)	0.0225 (2)	0.0301 (2)	−0.00600 (13)	0.00312 (13)	0.00353 (15)
Cl1	0.0542 (6)	0.0461 (5)	0.0682 (6)	−0.0106 (4)	0.0040 (4)	0.0314 (4)
Cl4	0.0390 (5)	0.0648 (6)	0.0921 (8)	0.0136 (4)	−0.0025 (5)	0.0498 (6)
Cl6	0.0311 (5)	0.0322 (5)	0.1425 (12)	−0.0079 (3)	−0.0069 (5)	0.0329 (5)
Cl2	0.0673 (7)	0.0517 (6)	0.0537 (6)	−0.0014 (5)	0.0007 (5)	0.0010 (4)
Cl3	0.0299 (5)	0.0347 (5)	0.1577 (13)	0.0097 (4)	−0.0054 (6)	0.0295 (6)
Cl5	0.0955 (9)	0.0523 (6)	0.0649 (7)	0.0291 (6)	0.0273 (6)	0.0068 (5)
N7	0.0274 (12)	0.0239 (12)	0.0307 (12)	−0.0021 (9)	0.0016 (9)	0.0032 (9)
N3	0.0265 (12)	0.0227 (12)	0.0352 (13)	−0.0011 (9)	0.0000 (9)	0.0045 (9)
N1	0.0220 (12)	0.0265 (12)	0.0366 (13)	−0.0031 (9)	0.0016 (9)	0.0072 (10)
O1	0.0255 (11)	0.0243 (11)	0.0680 (16)	−0.0004 (8)	0.0045 (10)	0.0072 (10)
O3	0.0243 (11)	0.0312 (11)	0.0648 (16)	0.0079 (9)	−0.0020 (10)	0.0193 (10)
C16	0.0235 (13)	0.0207 (13)	0.0377 (15)	0.0043 (10)	0.0042 (10)	0.0096 (10)
N5	0.0215 (11)	0.0241 (11)	0.0319 (12)	−0.0026 (9)	0.0001 (9)	0.0059 (9)
C14	0.0225 (14)	0.0250 (14)	0.056 (2)	0.0005 (11)	−0.0017 (12)	0.0128 (13)
N8	0.0403 (16)	0.0304 (14)	0.0435 (16)	−0.0018 (11)	0.0021 (12)	−0.0050 (12)
C15	0.0238 (14)	0.0259 (14)	0.058 (2)	0.0039 (11)	0.0032 (13)	0.0142 (13)
C4	0.0408 (18)	0.0237 (14)	0.0433 (18)	−0.0025 (12)	0.0015 (13)	0.0049 (12)
C3	0.0240 (14)	0.0353 (16)	0.0424 (17)	0.0007 (11)	0.0042 (11)	0.0144 (13)
N6	0.0193 (12)	0.0384 (14)	0.0436 (15)	0.0014 (10)	0.0066 (10)	0.0132 (11)
O2	0.0285 (12)	0.0370 (13)	0.0778 (19)	0.0111 (10)	0.0030 (11)	0.0239 (12)
C12	0.0413 (18)	0.0271 (15)	0.0458 (19)	0.0002 (13)	−0.0012 (14)	0.0075 (13)
N2	0.0210 (12)	0.0474 (16)	0.0459 (15)	−0.0026 (11)	0.0043 (10)	0.0184 (12)
C13	0.0260 (14)	0.0209 (13)	0.0437 (16)	0.0048 (10)	0.0085 (11)	0.0121 (11)
C9	0.0257 (14)	0.0303 (14)	0.0398 (16)	0.0050 (11)	0.0042 (11)	0.0132 (12)
C1	0.0252 (15)	0.0426 (18)	0.059 (2)	0.0046 (13)	0.0035 (13)	0.0259 (15)
N4	0.0420 (16)	0.0270 (14)	0.0465 (17)	−0.0031 (11)	−0.0039 (12)	−0.0062 (12)
C8	0.0301 (16)	0.0394 (18)	0.067 (2)	0.0030 (13)	0.0102 (15)	0.0290 (16)
C2	0.0341 (18)	0.049 (2)	0.056 (2)	−0.0062 (14)	0.0003 (14)	0.0309 (17)
C7	0.0255 (15)	0.0341 (16)	0.062 (2)	0.0053 (12)	0.0068 (13)	0.0243 (15)
C11	0.049 (2)	0.048 (2)	0.0307 (16)	−0.0056 (16)	0.0007 (13)	0.0033 (14)
C6	0.087 (3)	0.059 (3)	0.0338 (19)	−0.020 (2)	0.0015 (19)	−0.0010 (18)
C5	0.073 (3)	0.047 (2)	0.0355 (18)	−0.0206 (19)	−0.0033 (17)	0.0105 (15)
C10	0.048 (2)	0.0372 (17)	0.0346 (16)	0.0008 (14)	0.0011 (13)	0.0101 (13)
O4	0.0229 (10)	0.0261 (11)	0.0637 (16)	−0.0024 (8)	−0.0011 (9)	0.0102 (10)

Cu1—N7	1.997 (2)	N8—H8A	0.8600
Cu1—N3	2.001 (2)	C4—N4	1.327 (4)
Cu1—N1	2.011 (3)	C4—H4A	0.9300
Cu1—N5	2.022 (3)	C3—N2	1.333 (4)
Cu1—O3	2.479 (2)	C3—H3A	0.9300
Cu1—O2	2.618 (2)	N6—C9	1.333 (4)
Cl1—C14	1.768 (4)	N6—C8	1.367 (4)
Cl4—C15	1.767 (4)	N6—H6A	0.8600
Cl6—C15	1.757 (3)	O2—C13	1.220 (4)
Cl2—C14	1.778 (4)	C12—H12A	0.9300
Cl3—C14	1.754 (3)	N2—C2	1.364 (5)
Cl5—C15	1.768 (4)	N2—H2A	0.8600
N7—C12	1.325 (4)	C9—H9A	0.9300
N7—C10	1.370 (4)	C1—C2	1.353 (5)
N3—C4	1.328 (4)	C1—H1A	0.9300
N3—C5	1.362 (5)	N4—C6	1.350 (6)
N1—C3	1.316 (4)	N4—H4B	0.8600
N1—C1	1.375 (4)	C8—C7	1.348 (5)
O1—C13	1.240 (4)	C8—H8B	0.9300
O3—C16	1.226 (4)	C2—H2B	0.9300
C16—O4	1.245 (4)	C7—H7A	0.9300
C16—C15	1.565 (4)	C11—C10	1.358 (5)
N5—C9	1.312 (4)	C11—H11A	0.9300
N5—C7	1.372 (4)	C6—C5	1.357 (5)
C14—C13	1.582 (4)	C6—H6B	0.9300
N8—C12	1.339 (5)	C5—H5A	0.9300
N8—C11	1.358 (5)	C10—H10A	0.9300
N7—Cu1—N3	178.78 (10)	N3—C4—H4A	124.3
N7—Cu1—N1	87.99 (10)	N1—C3—N2	110.6 (3)
N3—Cu1—N1	90.80 (11)	N1—C3—H3A	124.7
N7—Cu1—N5	91.08 (10)	N2—C3—H3A	124.7
N3—Cu1—N5	90.11 (10)	C9—N6—C8	107.4 (3)
N1—Cu1—N5	175.95 (10)	C9—N6—H6A	126.3
N7—Cu1—O3	88.90 (10)	C8—N6—H6A	126.3
N3—Cu1—O3	91.37 (9)	N7—C12—N8	110.6 (3)
N1—Cu1—O3	95.17 (9)	N7—C12—H12A	124.7
N5—Cu1—O3	88.70 (9)	N8—C12—H12A	124.7
N7—Cu1—O2	88.42 (10)	C3—N2—C2	108.2 (3)
N3—Cu1—O2	91.36 (10)	C3—N2—H2A	125.9
N1—Cu1—O2	87.03 (9)	C2—N2—H2A	125.9
N5—Cu1—O2	89.06 (9)	O2—C13—O1	129.8 (3)
O3—Cu1—O2	176.47 (7)	O2—C13—C14	113.8 (3)
C12—N7—C10	105.8 (3)	O1—C13—C14	116.3 (2)
C12—N7—Cu1	130.0 (2)	N5—C9—N6	111.3 (3)
C10—N7—Cu1	124.2 (2)	N5—C9—H9A	124.4
C4—N3—C5	104.8 (3)	N6—C9—H9A	124.4
C4—N3—Cu1	129.0 (2)	C2—C1—N1	109.2 (3)
C5—N3—Cu1	126.2 (2)	C2—C1—H1A	125.4
C3—N1—C1	106.1 (3)	N1—C1—H1A	125.4
C3—N1—Cu1	126.4 (2)	C4—N4—C6	107.9 (3)
C1—N1—Cu1	127.3 (2)	C4—N4—H4B	126.0
O3—C16—O4	129.6 (3)	C6—N4—H4B	126.0
O3—C16—C15	116.0 (3)	C7—C8—N6	106.1 (3)
O4—C16—C15	114.3 (2)	C7—C8—H8B	126.9
C9—N5—C7	105.8 (3)	N6—C8—H8B	126.9
C9—N5—Cu1	127.4 (2)	C1—C2—N2	105.9 (3)
C7—N5—Cu1	126.8 (2)	C1—C2—H2B	127.0
C13—C14—Cl3	114.2 (2)	N2—C2—H2B	127.0
C13—C14—Cl1	108.4 (2)	C8—C7—N5	109.4 (3)
Cl3—C14—Cl1	108.81 (19)	C8—C7—H7A	125.3
C13—C14—Cl2	108.8 (2)	N5—C7—H7A	125.3
Cl3—C14—Cl2	107.99 (19)	C10—C11—N8	106.2 (3)
Cl1—C14—Cl2	108.56 (17)	C10—C11—H11A	126.9
C12—N8—C11	108.0 (3)	N8—C11—H11A	126.9
C12—N8—H8A	126.0	N4—C6—C5	105.9 (4)
C11—N8—H8A	126.0	N4—C6—H6B	127.0
C16—C15—Cl6	112.6 (2)	C5—C6—H6B	127.0
C16—C15—Cl4	111.9 (2)	C6—C5—N3	110.0 (4)
Cl6—C15—Cl4	107.7 (2)	C6—C5—H5A	125.0
C16—C15—Cl5	106.0 (2)	N3—C5—H5A	125.0
Cl6—C15—Cl5	109.80 (19)	C11—C10—N7	109.4 (3)
Cl4—C15—Cl5	108.70 (17)	C11—C10—H10A	125.3
N4—C4—N3	111.3 (3)	N7—C10—H10A	125.3
N4—C4—H4A	124.3

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8A···O1i	0.86	2.03	2.885 (3)	177
N6—H6A···O4ii	0.86	2.02	2.854 (3)	164
N2—H2A···O1iii	0.86	1.96	2.790 (3)	162
N4—H4B···O4iv	0.86	1.93	2.764 (3)	162

Table 1

Selected bond lengths (Å)

Cu1—N7	1.997 (2)
Cu1—N3	2.001 (2)
Cu1—N1	2.011 (3)
Cu1—N5	2.022 (3)
Cu1—O3	2.479 (2)
Cu1—O2	2.618 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8A⋯O1i	0.86	2.03	2.885 (3)	177
N6—H6A⋯O4ii	0.86	2.02	2.854 (3)	164
N2—H2A⋯O1iii	0.86	1.96	2.790 (3)	162
N4—H4B⋯O4iv	0.86	1.93	2.764 (3)	162

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .