Poly[di-μ3-chlorido-[μ2-(3-pyrid­yl)(4-pyrid­yl)methanone-κ2N:N′]dicopper(I)]

Hittle, J.L.; LaDuca, R.L.

doi:10.1107/S1600536808038385

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page m1599

doi:10.1107/S1600536808038385

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Poly[di-μ₃-chlorido-[μ₂-(3-pyridyl)(4-pyridyl)methanone-κ²N:N′]dicopper(I)]

Jennifer L. Hittle ^a and Robert L. LaDuca ^a ^*

^aLyman Briggs College, Department of Chemistry, Michigan State University, East Lansing, MI 48825, USA
^*Correspondence e-mail: laduca@msu.edu

(Received 6 November 2008; accepted 17 November 2008; online 22 November 2008)

In the title compound, [Cu₂Cl₂(C₁₁H₈N₂O)]_n, stair-like ribbons of formula [Cu₂Cl₂]_n are linked into coordination polymer layers by tethering (3-pyridyl)(4-pyridyl)methanone (3,4′-dpk) ligands. The two distinct Cu^I centres both adopt distorted CuNCl₃ tetrahedral coordinations. Individual [Cu₂Cl₂(3,4′-dpk)]_n layers stack in an AB pattern along the c direction by way of weak C—H⋯O interactions between the pyridyl rings and ketone O atoms.

Related literature

For copper molybdate coordination polymers with (3-pyridyl)(4-pyridyl)methanone and the synthesis of this ligand, see: Montney & LaDuca (2008 ). For data-handling software, see: Sheldrick (2003 ).

Experimental

Crystal data

[Cu₂Cl₂(C₁₁H₈N₂O)]
M_r = 382.17
Monoclinic, P 2₁ /c
a = 3.7765 (7) Å
b = 25.935 (5) Å
c = 12.339 (2) Å
β = 94.462 (3)°
V = 1204.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 3.96 mm⁻¹
T = 173 (2) K
0.22 × 0.14 × 0.08 mm

Data collection

Bruker SMART 1K CCD diffractometer
Absorption correction: multi-scan (TWINABS; Sheldrick, 2007 ) T_min = 0.503, T_max = 0.731
20010 measured reflections
2794 independent reflections
2435 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.095
S = 1.06
2794 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.97 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—N1	1.995 (3)
Cu1—Cl2	2.2787 (10)
Cu1—Cl2ⁱ	2.4081 (10)
Cu1—Cl1	2.5854 (11)
Cu2—N2ⁱⁱ	2.002 (3)
Cu2—Cl1	2.3173 (10)
Cu2—Cl1ⁱ	2.4118 (10)
Cu2—Cl2ⁱ	2.5343 (11)
Symmetry codes: (i) x-1, y, z; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱⁱⁱ	0.93	2.35	3.112 (5)	139
Symmetry code: (iii) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2003 ); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalMaker (Palmer, 2007 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038385/hb2839sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038385/hb2839Isup2.hkl

checkCIF report

Comment top

The kinked-donor disposed dipodal tethering ligand (3-pyridyl)(4-pyridyl)methanone (3,4'-dpk) has been rarely utilized for the construction of coordination polymer solids. Two copper molybdate phases incoporating this ligand have been reported recently (Montney & LaDuca, 2008). In an attempt to extend this chemistry into dicarboxylate systems, yellow crystals of the title compound, (I), were obtained.

The asymmetric unit of (I) contains two monovalent copper atoms, two chloride ions and one complete 3,4'-dpk ligand (Fig. 1). The coordination environment at each Cu atom is a distorted {CuCl₃N} tetrahedron (Table 1). The Cu and Cl atoms link into [Cu₂Cl₂]_n stair-like ribbons that are oriented parallel to the a crystal direction. The Cu···Cu distances across the `steps' of the stair-like ribbons measure 2.857 (1) Å and 3.153 (1) Å, respectively.

Parallel [Cu₂Cl₂]_n ribbons are covalently connected into [Cu₂Cl₂(3,4'-dpk)]_n coordination polymer layers, arranged parallel to the ab crystal planes, via the tethering 3,4'-dpk ligands (Fig. 2). The Cu···Cu contact distances across the diimine ligands measure 11.573 (3) Å. The dihedral angle between the pyridyl rings within a 3,4'-dpk ligand is 46.53 (17)°. Individual [Cu₂Cl₂(3,4'-dpk)]_n layers stack in an AB pattern along the c crystal direction through weak C—H···O supramolecular interactions between the pyridyl rings and ketone O atoms (Fig. 3), with a C···O contact distance of 3.112 (5) Å (Table 2).

Related literature top

For copper molybdate coordination polymers with (3-pyridyl)(4-pyridyl)methanone and the synthesis of this ligand, see: Montney & LaDuca (2008). For data-handling software, see: Sheldrick (2003).

Experimental top

All chemicals were obtained commercially with the exception of (3-pyridyl)(4-pyridyl)methanone (Montney & LaDuca, 2008). A mixture of copper(II) chloride dihydrate (63 mg, 0.37 mmol), phthalic acid (61 mg, 0.37 mmol), (3-pyridyl)(4-pyridyl)methanone (136 mg, 0.74 mmol) and 10.0 g water (555 mmol) was placed in a 23 ml Teflon-lined Parr acid digestion bomb, which was then heated under autogenous pressure at 393 K for 48 h. Yellow–orange blocks of (I) were obtained.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalMaker (Palmer, 2007); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Asymmetric unit of (I), expanded to show the metal coordination spheres, showing 50% probability ellipsoids. Hydrogen atom positions are shown as gray sticks. Symmetry codes: (1) x - 1, y, z (ii) -x, y - 1/2, -z + 1/2
	Fig. 2. A single [Cu₂Cl₂(3,4'-dpk)]_n layer in (I) formed by the linkage of [Cu₂Cl₂]_n ladders through the diimine ligands.
	Fig. 3. Packing diagram illustrating the AB layer stacking pattern, which forms the 3-D crystal structure of (I) through weak C—H···O interactions between pyridyl rings and ketone O atoms.

Poly[di-µ₃-chlorido-[µ₂-(3-pyridyl)(4-pyridyl)methanone- κ²N:N']dicopper(I)] top

Crystal data top

[Cu₂Cl₂(C₁₁H₈N₂O)]	F(000) = 752
M_r = 382.17	D_x = 2.107 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 20010 reflections
a = 3.7765 (7) Å	θ = 1.6–28.3°
b = 25.935 (5) Å	µ = 3.96 mm⁻¹
c = 12.339 (2) Å	T = 173 K
β = 94.462 (3)°	Block, yellow
V = 1204.9 (4) Å³	0.22 × 0.14 × 0.08 mm
Z = 4

Data collection top

Bruker SMART 1K CCD diffractometer	2794 independent reflections
Radiation source: fine-focus sealed tube	2435 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scans	θ_max = 28.3°, θ_min = 1.6°
Absorption correction: multi-scan (TWINABS; Sheldrick, 2007)	h = −5→4
T_min = 0.503, T_max = 0.731	k = 0→34
20010 measured reflections	l = 0→16

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0339P)² + 4.4918P] where P = (F_o² + 2F_c²)/3
2794 reflections	(Δ/σ)_max = 0.001
163 parameters	Δρ_max = 0.97 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[Cu₂Cl₂(C₁₁H₈N₂O)]	V = 1204.9 (4) Å³
M_r = 382.17	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 3.7765 (7) Å	µ = 3.96 mm⁻¹
b = 25.935 (5) Å	T = 173 K
c = 12.339 (2) Å	0.22 × 0.14 × 0.08 mm
β = 94.462 (3)°

Data collection top

Bruker SMART 1K CCD diffractometer	2794 independent reflections
Absorption correction: multi-scan (TWINABS; Sheldrick, 2007)	2435 reflections with I > 2σ(I)
T_min = 0.503, T_max = 0.731	R_int = 0.042
20010 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.06	Δρ_max = 0.97 e Å⁻³
2794 reflections	Δρ_min = −0.48 e Å⁻³
163 parameters

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 for the major twin component. 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

	x	y	z	U_iso*/U_eq
Cu1	0.30817 (14)	0.633401 (18)	0.12987 (4)	0.03284 (15)
Cu2	−0.09246 (14)	0.576023 (18)	0.27566 (4)	0.03282 (15)
Cl1	0.4078 (2)	0.62217 (3)	0.33820 (6)	0.01995 (17)
Cl2	0.7724 (2)	0.58732 (3)	0.07265 (7)	0.02118 (18)
N1	0.1879 (8)	0.70719 (11)	0.0999 (2)	0.0217 (6)
C2	0.2012 (9)	0.79762 (13)	0.1460 (3)	0.0186 (6)
N2	0.1356 (8)	0.99919 (11)	0.2175 (2)	0.0228 (6)
C8	0.2454 (9)	0.89246 (12)	0.2191 (3)	0.0193 (7)
C7	0.1332 (10)	0.91779 (14)	0.3097 (3)	0.0237 (7)
H7	0.0973	0.8995	0.3728	0.028*
C1	0.2845 (9)	0.74576 (13)	0.1677 (3)	0.0205 (7)
H1	0.4139	0.7378	0.2327	0.025*
O1	0.4939 (9)	0.82138 (10)	0.3137 (2)	0.0371 (7)
C9	0.2995 (9)	0.92152 (14)	0.1272 (3)	0.0224 (7)
H9	0.3696	0.9058	0.0646	0.027*
C5	−0.0002 (10)	0.71977 (14)	0.0055 (3)	0.0238 (7)
H5	−0.0729	0.6934	−0.0423	0.029*
C4	−0.0885 (10)	0.76977 (14)	−0.0230 (3)	0.0236 (7)
H4	−0.2124	0.7768	−0.0895	0.028*
C3	0.0094 (9)	0.80956 (13)	0.0486 (3)	0.0210 (7)
H3	−0.0523	0.8435	0.0316	0.025*
C10	0.2469 (9)	0.97448 (13)	0.1308 (3)	0.0216 (7)
H10	0.2911	0.9939	0.0699	0.026*
C6	0.0756 (10)	0.97045 (14)	0.3052 (3)	0.0252 (7)
H6	−0.0083	0.9867	0.3653	0.030*
C11	0.3264 (10)	0.83580 (13)	0.2312 (3)	0.0218 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0365 (3)	0.0196 (2)	0.0417 (3)	0.00451 (19)	−0.0013 (2)	−0.0024 (2)
Cu2	0.0436 (3)	0.0188 (2)	0.0359 (3)	−0.0030 (2)	0.0024 (2)	−0.00250 (19)
Cl1	0.0204 (4)	0.0227 (4)	0.0165 (4)	−0.0004 (3)	−0.0001 (3)	−0.0049 (3)
Cl2	0.0234 (4)	0.0203 (4)	0.0197 (4)	0.0012 (3)	0.0005 (3)	−0.0002 (3)
N1	0.0223 (15)	0.0191 (14)	0.0232 (15)	0.0003 (11)	−0.0024 (11)	0.0000 (11)
C2	0.0198 (16)	0.0178 (15)	0.0181 (15)	0.0006 (12)	0.0008 (12)	−0.0004 (12)
N2	0.0243 (15)	0.0187 (14)	0.0251 (15)	−0.0012 (11)	0.0001 (12)	−0.0002 (12)
C8	0.0227 (17)	0.0155 (15)	0.0191 (16)	−0.0016 (12)	−0.0020 (13)	−0.0007 (12)
C7	0.035 (2)	0.0209 (17)	0.0149 (16)	−0.0059 (14)	0.0029 (14)	−0.0002 (13)
C1	0.0234 (17)	0.0195 (16)	0.0177 (16)	0.0010 (13)	−0.0035 (13)	0.0006 (13)
O1	0.0581 (19)	0.0229 (13)	0.0270 (14)	0.0042 (13)	−0.0178 (13)	−0.0015 (11)
C9	0.0263 (18)	0.0235 (17)	0.0174 (16)	0.0006 (14)	0.0021 (13)	−0.0013 (13)
C5	0.0278 (18)	0.0210 (16)	0.0219 (17)	−0.0008 (14)	−0.0021 (14)	−0.0069 (14)
C4	0.0273 (19)	0.0265 (18)	0.0162 (16)	0.0018 (14)	−0.0040 (13)	0.0006 (13)
C3	0.0235 (17)	0.0200 (16)	0.0192 (16)	0.0032 (13)	0.0002 (13)	0.0022 (13)
C10	0.0233 (17)	0.0224 (17)	0.0190 (16)	−0.0014 (13)	0.0009 (13)	0.0043 (13)
C6	0.035 (2)	0.0191 (17)	0.0219 (17)	−0.0034 (14)	0.0056 (15)	−0.0053 (14)
C11	0.0265 (18)	0.0185 (16)	0.0197 (16)	0.0001 (13)	−0.0025 (13)	0.0010 (13)

Geometric parameters (Å, º) top

Cu1—N1	1.995 (3)	C8—C9	1.390 (5)
Cu1—Cl2	2.2787 (10)	C8—C7	1.391 (5)
Cu1—Cl2ⁱ	2.4081 (10)	C8—C11	1.506 (5)
Cu1—Cl1	2.5854 (11)	C7—C6	1.383 (5)
Cu2—N2ⁱⁱ	2.002 (3)	C7—H7	0.9300
Cu2—Cl1	2.3173 (10)	C1—H1	0.9300
Cu2—Cl1ⁱ	2.4118 (10)	O1—C11	1.216 (4)
Cu2—Cl2ⁱ	2.5343 (11)	C9—C10	1.389 (5)
N1—C1	1.336 (4)	C9—H9	0.9300
N1—C5	1.356 (5)	C5—C4	1.378 (5)
C2—C3	1.389 (5)	C5—H5	0.9300
C2—C1	1.403 (5)	C4—C3	1.390 (5)
C2—C11	1.494 (5)	C4—H4	0.9300
N2—C10	1.343 (5)	C3—H3	0.9300
N2—C6	1.348 (5)	C10—H10	0.9300
N2—Cu2ⁱⁱⁱ	2.002 (3)	C6—H6	0.9300

N1—Cu1—Cl2	127.98 (9)	C10—N2—Cu2ⁱⁱⁱ	122.7 (2)
N1—Cu1—Cl2ⁱ	104.34 (9)	C6—N2—Cu2ⁱⁱⁱ	119.9 (2)
Cl2—Cu1—Cl2ⁱ	107.34 (4)	C9—C8—C7	118.2 (3)
N1—Cu1—Cl1	107.80 (9)	C9—C8—C11	124.6 (3)
Cl2—Cu1—Cl1	101.13 (3)	C7—C8—C11	117.0 (3)
Cl2ⁱ—Cu1—Cl1	106.83 (3)	C6—C7—C8	119.4 (3)
N1—Cu1—Cu2	119.49 (9)	C6—C7—H7	120.3
Cl2—Cu1—Cu2	112.32 (3)	C8—C7—H7	120.3
Cl2ⁱ—Cu1—Cu2	56.78 (3)	N1—C1—C2	123.5 (3)
Cl1—Cu1—Cu2	50.09 (2)	N1—C1—H1	118.2
N2ⁱⁱ—Cu2—Cl1	124.54 (9)	C2—C1—H1	118.2
N2ⁱⁱ—Cu2—Cl1ⁱ	114.36 (9)	C10—C9—C8	118.7 (3)
Cl1—Cu2—Cl1ⁱ	105.97 (4)	C10—C9—H9	120.7
N2ⁱⁱ—Cu2—Cl2ⁱ	98.38 (9)	C8—C9—H9	120.7
Cl1—Cu2—Cl2ⁱ	111.46 (3)	N1—C5—C4	123.1 (3)
Cl1ⁱ—Cu2—Cl2ⁱ	99.00 (3)	N1—C5—H5	118.5
N2ⁱⁱ—Cu2—Cu1	126.42 (9)	C4—C5—H5	118.5
Cl1—Cu2—Cu1	58.85 (3)	C5—C4—C3	119.3 (3)
Cl1ⁱ—Cu2—Cu1	114.14 (3)	C5—C4—H4	120.3
Cl2ⁱ—Cu2—Cu1	52.64 (3)	C3—C4—H4	120.3
Cu2—Cl1—Cu2^iv	105.97 (4)	C2—C3—C4	118.7 (3)
Cu2—Cl1—Cu1	71.05 (3)	C2—C3—H3	120.7
Cu2^iv—Cl1—Cu1	78.15 (3)	C4—C3—H3	120.7
Cu1—Cl2—Cu1^iv	107.34 (4)	N2—C10—C9	123.5 (3)
Cu1—Cl2—Cu2^iv	81.67 (3)	N2—C10—H10	118.3
Cu1^iv—Cl2—Cu2^iv	70.58 (3)	C9—C10—H10	118.3
C1—N1—C5	117.2 (3)	N2—C6—C7	122.9 (3)
C1—N1—Cu1	123.7 (2)	N2—C6—H6	118.6
C5—N1—Cu1	119.1 (2)	C7—C6—H6	118.6
C3—C2—C1	118.2 (3)	O1—C11—C2	120.1 (3)
C3—C2—C11	125.2 (3)	O1—C11—C8	118.1 (3)
C1—C2—C11	116.6 (3)	C2—C11—C8	121.8 (3)
C10—N2—C6	117.3 (3)

N1—Cu1—Cu2—N2ⁱⁱ	158.68 (15)	Cl2—Cu1—N1—C1	−95.8 (3)
Cl2—Cu1—Cu2—N2ⁱⁱ	−26.27 (12)	Cl2ⁱ—Cu1—N1—C1	138.1 (3)
Cl2ⁱ—Cu1—Cu2—N2ⁱⁱ	70.41 (11)	Cl1—Cu1—N1—C1	24.8 (3)
Cl1—Cu1—Cu2—N2ⁱⁱ	−112.18 (12)	Cu2—Cu1—N1—C1	78.4 (3)
N1—Cu1—Cu2—Cl1	−89.14 (10)	Cl2—Cu1—N1—C5	83.7 (3)
Cl2—Cu1—Cu2—Cl1	85.91 (4)	Cl2ⁱ—Cu1—N1—C5	−42.4 (3)
Cl2ⁱ—Cu1—Cu2—Cl1	−177.41 (4)	Cl1—Cu1—N1—C5	−155.8 (3)
N1—Cu1—Cu2—Cl1ⁱ	5.53 (10)	Cu2—Cu1—N1—C5	−102.1 (3)
Cl2—Cu1—Cu2—Cl1ⁱ	−179.41 (4)	C9—C8—C7—C6	0.8 (5)
Cl2ⁱ—Cu1—Cu2—Cl1ⁱ	−82.74 (4)	C11—C8—C7—C6	176.2 (3)
Cl1—Cu1—Cu2—Cl1ⁱ	94.67 (4)	C5—N1—C1—C2	0.1 (5)
N1—Cu1—Cu2—Cl2ⁱ	88.27 (10)	Cu1—N1—C1—C2	179.6 (3)
Cl2—Cu1—Cu2—Cl2ⁱ	−96.67 (4)	C3—C2—C1—N1	−0.3 (5)
Cl1—Cu1—Cu2—Cl2ⁱ	177.41 (4)	C11—C2—C1—N1	179.3 (3)
N2ⁱⁱ—Cu2—Cl1—Cu2^iv	44.13 (12)	C7—C8—C9—C10	1.4 (5)
Cl1ⁱ—Cu2—Cl1—Cu2^iv	180.0	C11—C8—C9—C10	−173.6 (3)
Cl2ⁱ—Cu2—Cl1—Cu2^iv	−73.30 (4)	C1—N1—C5—C4	0.9 (6)
Cu1—Cu2—Cl1—Cu2^iv	−71.09 (3)	Cu1—N1—C5—C4	−178.6 (3)
N2ⁱⁱ—Cu2—Cl1—Cu1	115.22 (11)	N1—C5—C4—C3	−1.7 (6)
Cl1ⁱ—Cu2—Cl1—Cu1	−108.91 (3)	C1—C2—C3—C4	−0.5 (5)
Cl2ⁱ—Cu2—Cl1—Cu1	−2.21 (3)	C11—C2—C3—C4	179.9 (3)
N1—Cu1—Cl1—Cu2	113.91 (9)	C5—C4—C3—C2	1.5 (5)
Cl2—Cu1—Cl1—Cu2	−109.88 (4)	C6—N2—C10—C9	0.5 (5)
Cl2ⁱ—Cu1—Cl1—Cu2	2.26 (3)	Cu2ⁱⁱⁱ—N2—C10—C9	175.9 (3)
N1—Cu1—Cl1—Cu2^iv	−134.42 (9)	C8—C9—C10—N2	−2.1 (6)
Cl2—Cu1—Cl1—Cu2^iv	1.79 (3)	C10—N2—C6—C7	1.8 (6)
Cl2ⁱ—Cu1—Cl1—Cu2^iv	113.93 (3)	Cu2ⁱⁱⁱ—N2—C6—C7	−173.7 (3)
Cu2—Cu1—Cl1—Cu2^iv	111.67 (3)	C8—C7—C6—N2	−2.5 (6)
N1—Cu1—Cl2—Cu1^iv	55.05 (12)	C3—C2—C11—O1	−179.8 (4)
Cl2ⁱ—Cu1—Cl2—Cu1^iv	180.0	C1—C2—C11—O1	0.6 (5)
Cl1—Cu1—Cl2—Cu1^iv	−68.25 (4)	C3—C2—C11—C8	1.3 (5)
Cu2—Cu1—Cl2—Cu1^iv	−119.49 (3)	C1—C2—C11—C8	−178.3 (3)
N1—Cu1—Cl2—Cu2^iv	121.61 (11)	C9—C8—C11—O1	131.7 (4)
Cl2ⁱ—Cu1—Cl2—Cu2^iv	−113.44 (3)	C7—C8—C11—O1	−43.4 (5)
Cl1—Cu1—Cl2—Cu2^iv	−1.69 (3)	C9—C8—C11—C2	−49.4 (5)
Cu2—Cu1—Cl2—Cu2^iv	−52.93 (3)	C7—C8—C11—C2	135.5 (4)

Symmetry codes: (i) x−1, y, z; (ii) −x, y−1/2, −z+1/2; (iii) −x, y+1/2, −z+1/2; (iv) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1^v	0.93	2.35	3.112 (5)	139

Symmetry code: (v) x−1, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Cu₂Cl₂(C₁₁H₈N₂O)]
M_r	382.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	3.7765 (7), 25.935 (5), 12.339 (2)
β (°)	94.462 (3)
V (Å³)	1204.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.96
Crystal size (mm)	0.22 × 0.14 × 0.08

Data collection
Diffractometer	Bruker SMART 1K CCD diffractometer
Absorption correction	Multi-scan (TWINABS; Sheldrick, 2007)
T_min, T_max	0.503, 0.731
No. of measured, independent and observed [I > 2σ(I)] reflections	20010, 2794, 2435
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.095, 1.06
No. of reflections	2794
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.97, −0.48

Computer programs: SMART (Bruker, 2003), SAINT-Plus (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalMaker (Palmer, 2007).

Selected bond lengths (Å) top

Cu1—N1	1.995 (3)	Cu2—N2ⁱⁱ	2.002 (3)
Cu1—Cl2	2.2787 (10)	Cu2—Cl1	2.3173 (10)
Cu1—Cl2ⁱ	2.4081 (10)	Cu2—Cl1ⁱ	2.4118 (10)
Cu1—Cl1	2.5854 (11)	Cu2—Cl2ⁱ	2.5343 (11)

Symmetry codes: (i) x−1, y, z; (ii) −x, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱⁱⁱ	0.93	2.35	3.112 (5)	139

Symmetry code: (iii) x−1, −y+3/2, z−1/2.

Acknowledgements

The authors gratefully acknowledge the donors of the American Chemical Society Petroleum Research Fund for funding this work.

References

Bruker (2003). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Montney, M. R. & LaDuca, R. L. (2008). J. Solid State Chem. 181, 828—836. Web of Science CSD CrossRef Google Scholar
Palmer, D. (2007). Crystal Maker. CrystalMaker Software, Bicester, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2003). CELL-NOW. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2007). TWINABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar