rac-Dichlorido[3-eth-oxy-3-(1-ethyl-1H-benzimidazol-2-yl)-2,3-dihydro-1H-pyrrolo-[1,2-a]benzimidazole]-copper(II).

The title complex, [CuCl(2)(C(21)H(22)N(4)O)], contains a bis-(benzimidazole) unit with a chiral bridgehead C atom that forms part of a tetra-hydro-pyrrole ring fused to one of the benzimidazoles. The chelate angle is 90.45 (9)° and the dihedral angle between the essentially planar benzimidazole fragments is 26.68 (9)°. The Cu(II) coordination geometry lies approximately midway between tetra-hedral and square planar. Overall, each chiral mol-ecule contains six fused rings, and a racemic mixture is formed with symmetry-related enanti-omers. In the crystal, C-H⋯π and C-H⋯Cl inter-actions link mol-ecules into a supra-molecular chain along the a-axis direction.

Related literature

For 19F NMR studies of related compounds, see: Stibrany (2003 ▶). For polymerization studies, see: Stibrany et al. (2003 ▶). For their use as agents to study electron transfer, see: Knapp et al. (1990 ▶). For related structures, see: Baugh et al. (2006 ▶); Stibrany (2009 ▶); Stibrany et al. (2002 ▶, 2004 ▶); Stibrany & Potenza (2006 ▶, 2008 ▶). For calculation of the four-coordination geometry, see: Yang et al. (2007 ▶).

Experimental

Crystal data

[CuCl2(C21H22N4O)]

M = 480.87

Triclinic,

a = 8.9409 (17) Å

b = 9.5209 (18) Å

c = 14.323 (3) Å

α = 106.973 (4)°

β = 92.373 (4)°

γ = 113.778 (4)°

V = 1049.3 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.32 mm−1

T = 294 K

0.43 × 0.23 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000; ▶ Blessing, 1995 ▶) T min = 0.771, T max = 1.00

10062 measured reflections

4126 independent reflections

3380 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.124

S = 1.00

4126 reflections

264 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.90 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812051641/tk5184sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051641/tk5184Isup2.hkl

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

[CuCl2(C21H22N4O)]	Z = 2
Mr = 480.87	F(000) = 494
Triclinic, P1	Dx = 1.522 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9409 (17) Å	Cell parameters from 897 reflections
b = 9.5209 (18) Å	θ = 5.0–50.8°
c = 14.323 (3) Å	µ = 1.32 mm−1
α = 106.973 (4)°	T = 294 K
β = 92.373 (4)°	Cleaved plate, yellow-green
γ = 113.778 (4)°	0.43 × 0.23 × 0.06 mm
V = 1049.3 (3) Å3

Bruker SMART CCD area-detector diffractometer	4126 independent reflections
Radiation source: fine-focus sealed tube	3380 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 26.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000; Blessing, 1995)	h = −11→11
Tmin = 0.771, Tmax = 1.00	k = −11→11
10062 measured reflections	l = −17→17

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0832P)2 + 0.250P] where P = (Fo2 + 2Fc2)/3
4126 reflections	(Δ/σ)max = 0.001
264 parameters	Δρmax = 0.90 e Å−3
1 restraint	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cu	−0.05985 (4)	1.12548 (4)	0.28616 (3)	0.04148 (15)
Cl1	−0.11321 (11)	1.17616 (13)	0.15011 (7)	0.0642 (3)
Cl2	−0.17411 (11)	1.26316 (11)	0.38646 (7)	0.0588 (2)
O1	0.0067 (3)	0.7244 (3)	0.15123 (16)	0.0505 (5)
N11	0.3553 (3)	1.0483 (3)	0.21160 (19)	0.0420 (6)
N13	0.1575 (3)	1.1244 (3)	0.25783 (17)	0.0375 (5)
N21	−0.0518 (3)	0.7479 (3)	0.36364 (18)	0.0410 (5)
N23	−0.1091 (3)	0.9408 (3)	0.33722 (18)	0.0411 (5)
C1	0.0961 (3)	0.8415 (3)	0.2462 (2)	0.0385 (6)
C3	−0.0847 (5)	0.7703 (5)	0.0917 (3)	0.0678 (10)
H3A	−0.0093	0.8600	0.0729	0.081*
H3B	−0.1594	0.8052	0.1287	0.081*
C4	−0.1818 (6)	0.6250 (7)	0.0011 (3)	0.1055 (19)
H4A	−0.1073	0.5879	−0.0329	0.158*
H4B	−0.2395	0.6545	−0.0421	0.158*
H4C	−0.2607	0.5393	0.0203	0.158*
C11	0.4096 (3)	1.2079 (3)	0.2130 (2)	0.0397 (6)
C12	0.2047 (3)	1.0057 (3)	0.2399 (2)	0.0365 (6)
C13	0.2862 (3)	1.2549 (3)	0.2426 (2)	0.0369 (6)
C14	0.3060 (4)	1.4126 (4)	0.2565 (2)	0.0466 (7)
H14	0.2250	1.4460	0.2777	0.056*
C15	0.4509 (4)	1.5166 (4)	0.2374 (3)	0.0513 (8)
H15	0.4679	1.6228	0.2455	0.062*
C16	0.5728 (4)	1.4675 (4)	0.2062 (2)	0.0516 (8)
H16	0.6685	1.5415	0.1933	0.062*
C17	0.5561 (4)	1.3137 (4)	0.1939 (2)	0.0483 (7)
H17	0.6383	1.2816	0.1738	0.058*
C18	0.4450 (4)	0.9499 (4)	0.1798 (3)	0.0625 (10)
H18A	0.5629	1.0211	0.1924	0.075*
H18B	0.4279	0.8787	0.2189	0.075*
C19	0.3921 (9)	0.8517 (9)	0.0753 (4)	0.145 (3)
H19A	0.2790	0.7719	0.0638	0.217*
H19B	0.4620	0.7976	0.0563	0.217*
H19C	0.4004	0.9206	0.0365	0.217*
C21	−0.1714 (3)	0.7566 (3)	0.4191 (2)	0.0407 (6)
C22	−0.0218 (3)	0.8560 (3)	0.3164 (2)	0.0375 (6)
C23	−0.2082 (3)	0.8786 (3)	0.4025 (2)	0.0397 (6)
C24	−0.3296 (4)	0.9138 (4)	0.4451 (3)	0.0535 (8)
H24	−0.3543	0.9952	0.4356	0.064*
C25	−0.4141 (4)	0.8241 (4)	0.5026 (3)	0.0575 (8)
H25	−0.4979	0.8445	0.5314	0.069*
C26	−0.3756 (4)	0.7040 (4)	0.5180 (2)	0.0526 (8)
H26	−0.4345	0.6463	0.5572	0.063*
C27	−0.2544 (4)	0.6675 (4)	0.4778 (2)	0.0497 (7)
H27	−0.2288	0.5876	0.4890	0.060*
C28	0.0448 (4)	0.6532 (4)	0.3416 (3)	0.0513 (8)
H28A	−0.0222	0.5433	0.2962	0.062*
H28B	0.0945	0.6486	0.4015	0.062*
C29	0.1774 (4)	0.7556 (4)	0.2925 (3)	0.0492 (7)
H29A	0.2095	0.6860	0.2417	0.059*
H29B	0.2755	0.8354	0.3416	0.059*

	U11	U22	U33	U12	U13	U23
Cu	0.0349 (2)	0.0438 (2)	0.0595 (3)	0.02188 (17)	0.01855 (16)	0.02833 (18)
Cl1	0.0509 (5)	0.0988 (7)	0.0767 (6)	0.0443 (5)	0.0264 (4)	0.0576 (5)
Cl2	0.0677 (5)	0.0548 (5)	0.0766 (6)	0.0398 (4)	0.0346 (4)	0.0319 (4)
O1	0.0545 (13)	0.0378 (11)	0.0488 (12)	0.0117 (10)	0.0105 (10)	0.0121 (9)
N11	0.0327 (12)	0.0374 (13)	0.0589 (15)	0.0155 (10)	0.0175 (10)	0.0186 (11)
N13	0.0279 (11)	0.0363 (12)	0.0499 (13)	0.0122 (10)	0.0101 (9)	0.0187 (10)
N21	0.0402 (13)	0.0358 (12)	0.0511 (14)	0.0155 (10)	0.0124 (10)	0.0215 (11)
N23	0.0384 (13)	0.0376 (13)	0.0543 (14)	0.0172 (11)	0.0173 (11)	0.0227 (11)
C1	0.0362 (14)	0.0312 (14)	0.0483 (15)	0.0146 (12)	0.0098 (11)	0.0133 (12)
C3	0.063 (2)	0.066 (2)	0.054 (2)	0.0090 (19)	−0.0028 (17)	0.0210 (18)
C4	0.091 (3)	0.102 (4)	0.058 (2)	−0.014 (3)	−0.003 (2)	0.020 (2)
C11	0.0328 (14)	0.0373 (15)	0.0468 (15)	0.0123 (12)	0.0087 (11)	0.0152 (12)
C12	0.0284 (13)	0.0365 (14)	0.0455 (15)	0.0133 (11)	0.0091 (11)	0.0157 (12)
C13	0.0304 (13)	0.0368 (14)	0.0425 (15)	0.0116 (11)	0.0056 (11)	0.0163 (12)
C14	0.0405 (16)	0.0413 (16)	0.0608 (19)	0.0179 (13)	0.0113 (13)	0.0209 (14)
C15	0.0447 (17)	0.0374 (16)	0.069 (2)	0.0128 (14)	0.0041 (15)	0.0222 (15)
C16	0.0336 (15)	0.0453 (17)	0.0633 (19)	0.0011 (13)	0.0041 (13)	0.0245 (15)
C17	0.0320 (15)	0.0505 (18)	0.0619 (19)	0.0141 (13)	0.0135 (13)	0.0233 (15)
C18	0.051 (2)	0.054 (2)	0.097 (3)	0.0285 (17)	0.0366 (19)	0.034 (2)
C19	0.128 (6)	0.139 (6)	0.143 (6)	0.072 (5)	0.030 (5)	−0.005 (5)
C21	0.0364 (14)	0.0371 (15)	0.0453 (15)	0.0114 (12)	0.0081 (12)	0.0157 (12)
C22	0.0338 (14)	0.0314 (14)	0.0451 (15)	0.0101 (11)	0.0074 (11)	0.0157 (12)
C23	0.0361 (14)	0.0333 (14)	0.0462 (16)	0.0103 (12)	0.0118 (12)	0.0150 (12)
C24	0.0511 (18)	0.0455 (18)	0.070 (2)	0.0229 (15)	0.0246 (16)	0.0241 (16)
C25	0.0498 (19)	0.054 (2)	0.067 (2)	0.0194 (16)	0.0293 (16)	0.0201 (17)
C26	0.0499 (18)	0.0497 (18)	0.0485 (17)	0.0088 (15)	0.0150 (14)	0.0211 (15)
C27	0.0501 (18)	0.0448 (17)	0.0517 (18)	0.0125 (14)	0.0109 (14)	0.0242 (14)
C28	0.0536 (18)	0.0479 (18)	0.068 (2)	0.0294 (16)	0.0194 (15)	0.0290 (16)
C29	0.0477 (17)	0.0435 (17)	0.068 (2)	0.0259 (14)	0.0170 (15)	0.0251 (15)

Cu—N23	1.993 (2)	C14—C15	1.373 (4)
Cu—N13	2.005 (2)	C14—H14	0.9300
Cu—Cl1	2.2169 (9)	C15—C16	1.391 (5)
Cu—Cl2	2.2198 (9)	C15—H15	0.9300
O1—C3	1.426 (4)	C16—C17	1.366 (5)
O1—C1	1.428 (3)	C16—H16	0.9300
N11—C12	1.357 (3)	C17—H17	0.9300
N11—C11	1.390 (4)	C18—C19	1.452 (6)
N11—C18	1.454 (4)	C18—H18A	0.9700
N13—C12	1.321 (4)	C18—H18B	0.9700
N13—C13	1.393 (4)	C19—H19A	0.9600
N21—C22	1.338 (3)	C19—H19B	0.9600
N21—C21	1.373 (4)	C19—H19C	0.9600
N21—C28	1.464 (4)	C21—C27	1.392 (4)
N23—C22	1.318 (4)	C21—C23	1.405 (4)
N23—C23	1.407 (3)	C23—C24	1.375 (4)
C1—C12	1.504 (4)	C24—C25	1.386 (5)
C1—C22	1.505 (4)	C24—H24	0.9300
C1—C29	1.546 (4)	C25—C26	1.391 (5)
C3—C4	1.498 (6)	C25—H25	0.9300
C3—H3A	0.9700	C26—C27	1.365 (5)
C3—H3B	0.9700	C26—H26	0.9300
C4—H4A	0.9600	C27—H27	0.9300
C4—H4B	0.9600	C28—C29	1.545 (4)
C4—H4C	0.9600	C28—H28A	0.9700
C11—C13	1.386 (4)	C28—H28B	0.9700
C11—C17	1.390 (4)	C29—H29A	0.9700
C13—C14	1.391 (4)	C29—H29B	0.9700
N23—Cu—N13	90.45 (9)	C17—C16—C15	121.9 (3)
N23—Cu—Cl1	141.12 (8)	C17—C16—H16	119.0
N13—Cu—Cl1	94.14 (7)	C15—C16—H16	119.0
N23—Cu—Cl2	100.17 (7)	C16—C17—C11	116.5 (3)
N13—Cu—Cl2	143.67 (8)	C16—C17—H17	121.8
Cl1—Cu—Cl2	98.64 (4)	C11—C17—H17	121.8
C3—O1—C1	116.9 (2)	C19—C18—N11	112.5 (4)
C12—N11—C11	106.7 (2)	C19—C18—H18A	109.1
C12—N11—C18	129.1 (3)	N11—C18—H18A	109.1
C11—N11—C18	124.2 (2)	C19—C18—H18B	109.1
C12—N13—C13	106.1 (2)	N11—C18—H18B	109.1
C12—N13—Cu	130.38 (19)	H18A—C18—H18B	107.8
C13—N13—Cu	123.17 (18)	C18—C19—H19A	109.5
C22—N21—C21	107.9 (2)	C18—C19—H19B	109.5
C22—N21—C28	114.1 (2)	H19A—C19—H19B	109.5
C21—N21—C28	138.0 (3)	C18—C19—H19C	109.5
C22—N23—C23	104.6 (2)	H19A—C19—H19C	109.5
C22—N23—Cu	118.62 (19)	H19B—C19—H19C	109.5
C23—N23—Cu	136.46 (19)	N21—C21—C27	132.3 (3)
O1—C1—C12	112.2 (2)	N21—C21—C23	105.3 (2)
O1—C1—C22	110.5 (2)	C27—C21—C23	122.3 (3)
C12—C1—C22	110.3 (2)	N23—C22—N21	113.5 (3)
O1—C1—C29	104.6 (2)	N23—C22—C1	135.6 (3)
C12—C1—C29	118.8 (2)	N21—C22—C1	110.7 (2)
C22—C1—C29	99.6 (2)	C24—C23—C21	120.1 (3)
O1—C3—C4	107.8 (4)	C24—C23—N23	131.1 (3)
O1—C3—H3A	110.1	C21—C23—N23	108.8 (2)
C4—C3—H3A	110.1	C23—C24—C25	117.9 (3)
O1—C3—H3B	110.1	C23—C24—H24	121.1
C4—C3—H3B	110.1	C25—C24—H24	121.1
H3A—C3—H3B	108.5	C24—C25—C26	121.0 (3)
C3—C4—H4A	109.5	C24—C25—H25	119.5
C3—C4—H4B	109.5	C26—C25—H25	119.5
H4A—C4—H4B	109.5	C27—C26—C25	122.5 (3)
C3—C4—H4C	109.5	C27—C26—H26	118.8
H4A—C4—H4C	109.5	C25—C26—H26	118.8
H4B—C4—H4C	109.5	C26—C27—C21	116.2 (3)
C13—C11—C17	122.0 (3)	C26—C27—H27	121.9
C13—C11—N11	106.4 (2)	C21—C27—H27	121.9
C17—C11—N11	131.6 (3)	N21—C28—C29	100.3 (2)
N13—C12—N11	112.2 (2)	N21—C28—H28A	111.7
N13—C12—C1	122.2 (2)	C29—C28—H28A	111.7
N11—C12—C1	125.5 (2)	N21—C28—H28B	111.7
C11—C13—C14	120.9 (3)	C29—C28—H28B	111.7
C11—C13—N13	108.6 (2)	H28A—C28—H28B	109.5
C14—C13—N13	130.4 (3)	C28—C29—C1	106.2 (2)
C15—C14—C13	116.8 (3)	C28—C29—H29A	110.5
C15—C14—H14	121.6	C1—C29—H29A	110.5
C13—C14—H14	121.6	C28—C29—H29B	110.5
C14—C15—C16	121.9 (3)	C1—C29—H29B	110.5
C14—C15—H15	119.1	H29A—C29—H29B	108.7
C16—C15—H15	119.1
N23—Cu—N13—C12	25.1 (3)	C14—C15—C16—C17	−0.8 (5)
Cl1—Cu—N13—C12	−116.3 (2)	C15—C16—C17—C11	0.8 (5)
Cl2—Cu—N13—C12	133.1 (2)	C13—C11—C17—C16	0.3 (5)
N23—Cu—N13—C13	−162.5 (2)	N11—C11—C17—C16	−177.3 (3)
Cl1—Cu—N13—C13	56.1 (2)	C12—N11—C18—C19	83.6 (5)
Cl2—Cu—N13—C13	−54.5 (3)	C11—N11—C18—C19	−92.7 (5)
N13—Cu—N23—C22	−15.8 (2)	C22—N21—C21—C27	176.2 (3)
Cl1—Cu—N23—C22	81.4 (2)	C28—N21—C21—C27	−2.1 (6)
Cl2—Cu—N23—C22	−160.9 (2)	C22—N21—C21—C23	−0.8 (3)
N13—Cu—N23—C23	156.1 (3)	C28—N21—C21—C23	−179.1 (3)
Cl1—Cu—N23—C23	−106.8 (3)	C23—N23—C22—N21	−1.5 (3)
Cl2—Cu—N23—C23	11.0 (3)	Cu—N23—C22—N21	172.72 (19)
C3—O1—C1—C12	−51.1 (3)	C23—N23—C22—C1	173.0 (3)
C3—O1—C1—C22	72.5 (3)	Cu—N23—C22—C1	−12.8 (4)
C3—O1—C1—C29	178.8 (3)	C21—N21—C22—N23	1.5 (3)
C1—O1—C3—C4	−174.3 (3)	C28—N21—C22—N23	−179.8 (3)
C12—N11—C11—C13	−0.1 (3)	C21—N21—C22—C1	−174.4 (2)
C18—N11—C11—C13	176.9 (3)	C28—N21—C22—C1	4.3 (3)
C12—N11—C11—C17	177.8 (3)	O1—C1—C22—N23	−86.1 (4)
C18—N11—C11—C17	−5.2 (5)	C12—C1—C22—N23	38.5 (4)
C13—N13—C12—N11	−1.3 (3)	C29—C1—C22—N23	164.2 (3)
Cu—N13—C12—N11	172.07 (19)	O1—C1—C22—N21	88.5 (3)
C13—N13—C12—C1	−178.6 (3)	C12—C1—C22—N21	−146.9 (2)
Cu—N13—C12—C1	−5.2 (4)	C29—C1—C22—N21	−21.1 (3)
C11—N11—C12—N13	0.9 (3)	N21—C21—C23—C24	177.6 (3)
C18—N11—C12—N13	−175.9 (3)	C27—C21—C23—C24	0.2 (5)
C11—N11—C12—C1	178.1 (3)	N21—C21—C23—N23	−0.1 (3)
C18—N11—C12—C1	1.3 (5)	C27—C21—C23—N23	−177.5 (3)
O1—C1—C12—N13	97.8 (3)	C22—N23—C23—C24	−176.4 (3)
C22—C1—C12—N13	−25.9 (4)	Cu—N23—C23—C24	11.0 (5)
C29—C1—C12—N13	−139.9 (3)	C22—N23—C23—C21	0.9 (3)
O1—C1—C12—N11	−79.1 (3)	Cu—N23—C23—C21	−171.7 (2)
C22—C1—C12—N11	157.2 (3)	C21—C23—C24—C25	−0.9 (5)
C29—C1—C12—N11	43.2 (4)	N23—C23—C24—C25	176.1 (3)
C17—C11—C13—C14	−1.4 (5)	C23—C24—C25—C26	1.0 (5)
N11—C11—C13—C14	176.7 (3)	C24—C25—C26—C27	−0.2 (5)
C17—C11—C13—N13	−178.8 (3)	C25—C26—C27—C21	−0.6 (5)
N11—C11—C13—N13	−0.7 (3)	N21—C21—C27—C26	−176.0 (3)
C12—N13—C13—C11	1.2 (3)	C23—C21—C27—C26	0.6 (4)
Cu—N13—C13—C11	−172.76 (18)	C22—N21—C28—C29	14.7 (3)
C12—N13—C13—C14	−175.9 (3)	C21—N21—C28—C29	−167.1 (3)
Cu—N13—C13—C14	10.1 (4)	N21—C28—C29—C1	−27.3 (3)
C11—C13—C14—C15	1.4 (5)	O1—C1—C29—C28	−84.9 (3)
N13—C13—C14—C15	178.2 (3)	C12—C1—C29—C28	149.1 (3)
C13—C14—C15—C16	−0.4 (5)	C22—C1—C29—C28	29.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···Cg1i	0.96	2.99	3.910 (5)	160
C17—H17···Cl1ii	0.93	2.78	3.694 (4)	169

Cu—N23	1.993 (2)
Cu—N13	2.005 (2)
Cu—Cl1	2.2169 (9)
Cu—Cl2	2.2198 (9)

N23—Cu—N13	90.45 (9)
N23—Cu—Cl1	141.12 (8)
N13—Cu—Cl1	94.14 (7)
N23—Cu—Cl2	100.17 (7)
N13—Cu—Cl2	143.67 (8)
Cl1—Cu—Cl2	98.64 (4)

Table 2

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C11/C13–C17 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4B⋯Cg1i	0.96	2.99	3.910 (5)	160
C17—H17⋯Cl1ii	0.93	2.78	3.694 (4)	169

Symmetry codes: (i) ; (ii) .