[2,2'-(1,1'-Binaphthyl-2,2'-diyldiimino)-diethanol-κN,N',O]dichloridocopper(II).

In the title complex, [CuCl(2)(C(24)H(24)N(2)O(2))], the Cu(II) cation is N,N',O-chelated by a 2,2'-(1,1'-binaphthyl-2,2'-diyldiimino)-diethanol ligand and coordinated by two chloride anions in a distorted square-pyramidal geometry. In the diethanol ligand, the two naphthalene ring systems are twisted with respect to each other at a dihedral angle of 68.30 (9)°. The uncoord-inated hy-droxy group links with a coordinated chloride anion via an intra-molecular O-H⋯Cl hydrogen bond. Inter-molecular N-H⋯O and N-H⋯Cl hydrogen bonds occur in the crystal structure.

Related literature

For background to metal complexes containing N-substituted diethano­lamine ligands, see: Saalfrank et al. (2008 ▶); Ferguson et al. (2011 ▶); Alley et al. (2008 ▶). For the synthesis of the ligand, see: Yan et al. (2008 ▶). For related structures, see: Thob et al. (2010 ▶); Telfer et al. (2004 ▶).

Experimental

Crystal data

[CuCl2(C24H24N2O2)]

M = 506.89

Triclinic,

a = 7.4816 (8) Å

b = 10.4211 (11) Å

c = 15.2116 (16) Å

α = 94.130 (2)°

β = 103.633 (2)°

γ = 106.912 (2)°

V = 1090.1 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.27 mm−1

T = 185 K

0.31 × 0.17 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.694, T max = 0.883

5452 measured reflections

3758 independent reflections

3363 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.107

S = 1.04

3758 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.40 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811049828/xu5393sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049828/xu5393Isup2.hkl

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

[CuCl2(C24H24N2O2)]	Z = 2
Mr = 506.89	F(000) = 522
Triclinic, P1	Dx = 1.544 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4816 (8) Å	Cell parameters from 3367 reflections
b = 10.4211 (11) Å	θ = 2.7–26.0°
c = 15.2116 (16) Å	µ = 1.27 mm−1
α = 94.130 (2)°	T = 185 K
β = 103.633 (2)°	Block, brown
γ = 106.912 (2)°	0.31 × 0.17 × 0.10 mm
V = 1090.1 (2) Å3

Bruker SMART 1000 CCD area-detector diffractometer	3758 independent reflections
Radiation source: fine-focus sealed tube	3363 reflections with I > 2σ(I)
graphite	Rint = 0.012
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→8
Tmin = 0.694, Tmax = 0.883	k = −12→12
5452 measured reflections	l = −18→11

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.070P)2 + 0.7465P] where P = (Fo2 + 2Fc2)/3
3758 reflections	(Δ/σ)max = 0.001
280 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Experimental. The elemental analysis, Ms, IR and 1H NMR, 13C NMR of the ligand are all in good agreement with the assumed structure. Analysis calculated (%) for C28H32N2O4: C, 73.02; H, 7.00; N, 6.08; Found: C, 73.53; H, 7.62; N, 5.76. IR (KBr, cm-1): 3369(s), 3055(w), 2936(m), 1617(s), 1594(s), 1504(s), 1468(m), 1424(m), 1358(s), 1199(w), 1147(m), 1046(s), 817(s), 750(s). 1H NMR (DMSO, 500 MHz) σ: 7.93–6.85 (m, 12H, ArH), 4.26 (m, 4H, CH2OH), 3.09 (M, 8H, CH2OH), 2.96 (M, 8H, NCH2CH2OH); 13C NMR (DMSO, 125.77 MHz) σ: 148.24, 134.54, 130.03, 128.80, 128.37, 126.51, 126.45, 125.88, 124.09, 122.93, 59.86, 55.67. ESI-Ms: M—H- peak at m/z 458.53.

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
Cu1	0.45715 (5)	0.32140 (3)	0.60514 (2)	0.02338 (13)
Cl1	0.78869 (9)	0.51803 (6)	0.65550 (5)	0.02669 (18)
Cl2	0.43545 (12)	0.20440 (8)	0.47249 (5)	0.0382 (2)
C1	0.3922 (4)	0.1142 (3)	0.71308 (18)	0.0228 (6)
C2	0.2759 (4)	−0.0126 (3)	0.6591 (2)	0.0299 (6)
H2	0.3104	−0.0450	0.6076	0.036*
C3	0.1151 (4)	−0.0876 (3)	0.6810 (2)	0.0307 (6)
H3	0.0398	−0.1732	0.6452	0.037*
C4	0.0582 (4)	−0.0404 (3)	0.75604 (19)	0.0248 (6)
C5	−0.1103 (4)	−0.1166 (3)	0.7790 (2)	0.0312 (6)
H5	−0.1858	−0.2029	0.7442	0.037*
C6	−0.1658 (4)	−0.0684 (3)	0.8502 (2)	0.0355 (7)
H6	−0.2783	−0.1210	0.8653	0.043*
C7	−0.0546 (4)	0.0606 (3)	0.9013 (2)	0.0348 (7)
H7	−0.0944	0.0953	0.9503	0.042*
C8	0.1083 (4)	0.1355 (3)	0.8814 (2)	0.0277 (6)
H8	0.1809	0.2218	0.9168	0.033*
C9	0.1722 (4)	0.0877 (3)	0.80891 (18)	0.0221 (5)
C10	0.3443 (4)	0.1644 (3)	0.78723 (17)	0.0205 (5)
C11	0.4725 (4)	0.2994 (3)	0.84286 (18)	0.0210 (5)
C12	0.5856 (4)	0.3070 (3)	0.93434 (18)	0.0222 (6)
C13	0.5791 (4)	0.1920 (3)	0.9794 (2)	0.0310 (6)
H13	0.4958	0.1052	0.9483	0.037*
C14	0.6904 (5)	0.2038 (3)	1.0668 (2)	0.0363 (7)
H14	0.6835	0.1251	1.0954	0.044*
C15	0.8152 (4)	0.3313 (3)	1.1149 (2)	0.0351 (7)
H15	0.8917	0.3385	1.1756	0.042*
C16	0.8251 (4)	0.4438 (3)	1.0737 (2)	0.0313 (7)
H16	0.9092	0.5296	1.1064	0.038*
C17	0.7126 (4)	0.4358 (3)	0.98322 (18)	0.0248 (6)
C18	0.7260 (4)	0.5509 (3)	0.9390 (2)	0.0277 (6)
H18	0.8135	0.6363	0.9705	0.033*
C19	0.6176 (4)	0.5433 (3)	0.85272 (19)	0.0252 (6)
H19	0.6288	0.6230	0.8249	0.030*
C20	0.4873 (4)	0.4167 (3)	0.80370 (18)	0.0208 (5)
N1	0.5583 (3)	0.1950 (2)	0.68647 (15)	0.0225 (5)
H1	0.6406	0.2511	0.7397	0.027*
N2	0.3739 (3)	0.4081 (2)	0.71187 (15)	0.0211 (5)
H2A	0.2494	0.3527	0.7087	0.025*
C23	0.3526 (4)	0.5384 (3)	0.6829 (2)	0.0278 (6)
H23A	0.4815	0.6032	0.6865	0.033*
H23B	0.2925	0.5797	0.7239	0.033*
C21	0.6734 (4)	0.1155 (3)	0.6551 (2)	0.0297 (6)
H21A	0.5928	0.0530	0.5983	0.036*
H21B	0.7091	0.0600	0.7022	0.036*
C24	0.2268 (4)	0.5076 (3)	0.5865 (2)	0.0314 (6)
H24A	0.0901	0.4603	0.5846	0.038*
H24B	0.2335	0.5923	0.5600	0.038*
C22	0.8557 (4)	0.2057 (3)	0.6372 (2)	0.0340 (7)
H22A	0.9313	0.1489	0.6200	0.041*
H22B	0.8197	0.2532	0.5850	0.041*
O1	0.9733 (3)	0.3032 (2)	0.71480 (15)	0.0362 (5)
H1A	0.9098	0.3518	0.7295	0.054*
O2	0.3005 (4)	0.4224 (3)	0.53688 (15)	0.0452 (6)
H2B	0.2296	0.3983	0.4829	0.068*

	U11	U22	U33	U12	U13	U23
Cu1	0.0258 (2)	0.0231 (2)	0.0227 (2)	0.00924 (14)	0.00696 (14)	0.00440 (13)
Cl1	0.0260 (3)	0.0260 (3)	0.0274 (4)	0.0071 (3)	0.0073 (3)	0.0045 (3)
Cl2	0.0523 (5)	0.0344 (4)	0.0266 (4)	0.0175 (3)	0.0057 (3)	−0.0017 (3)
C1	0.0228 (13)	0.0192 (12)	0.0251 (14)	0.0044 (10)	0.0060 (11)	0.0062 (10)
C2	0.0351 (16)	0.0236 (14)	0.0288 (15)	0.0053 (12)	0.0108 (13)	−0.0005 (11)
C3	0.0311 (15)	0.0207 (13)	0.0325 (16)	0.0002 (11)	0.0054 (13)	−0.0021 (12)
C4	0.0244 (14)	0.0208 (13)	0.0256 (14)	0.0045 (11)	0.0024 (11)	0.0073 (11)
C5	0.0277 (15)	0.0236 (14)	0.0384 (17)	0.0022 (11)	0.0082 (13)	0.0086 (12)
C6	0.0301 (15)	0.0339 (16)	0.0445 (18)	0.0061 (13)	0.0159 (14)	0.0160 (14)
C7	0.0376 (17)	0.0400 (17)	0.0335 (16)	0.0154 (14)	0.0168 (14)	0.0102 (13)
C8	0.0283 (14)	0.0254 (14)	0.0277 (15)	0.0066 (11)	0.0069 (12)	0.0022 (11)
C9	0.0239 (13)	0.0205 (13)	0.0211 (13)	0.0072 (10)	0.0027 (11)	0.0079 (10)
C10	0.0219 (13)	0.0181 (12)	0.0185 (13)	0.0052 (10)	0.0002 (11)	0.0060 (10)
C11	0.0193 (12)	0.0194 (12)	0.0229 (13)	0.0048 (10)	0.0058 (11)	−0.0001 (10)
C12	0.0188 (12)	0.0252 (14)	0.0219 (13)	0.0069 (10)	0.0053 (11)	−0.0007 (11)
C13	0.0319 (15)	0.0269 (14)	0.0302 (15)	0.0091 (12)	0.0016 (13)	0.0034 (12)
C14	0.0408 (18)	0.0399 (17)	0.0295 (16)	0.0174 (14)	0.0045 (14)	0.0098 (13)
C15	0.0295 (15)	0.0516 (19)	0.0222 (15)	0.0170 (14)	−0.0005 (12)	0.0002 (13)
C16	0.0227 (14)	0.0403 (17)	0.0253 (15)	0.0069 (12)	0.0035 (12)	−0.0072 (13)
C17	0.0209 (13)	0.0283 (14)	0.0239 (14)	0.0057 (11)	0.0086 (11)	−0.0028 (11)
C18	0.0243 (14)	0.0230 (13)	0.0310 (15)	0.0006 (11)	0.0100 (12)	−0.0063 (11)
C19	0.0260 (14)	0.0187 (13)	0.0316 (15)	0.0043 (11)	0.0125 (12)	0.0039 (11)
C20	0.0189 (12)	0.0202 (12)	0.0243 (14)	0.0061 (10)	0.0085 (11)	0.0002 (10)
N1	0.0224 (11)	0.0198 (11)	0.0235 (11)	0.0039 (9)	0.0071 (9)	0.0011 (9)
N2	0.0210 (11)	0.0171 (10)	0.0259 (12)	0.0056 (9)	0.0075 (9)	0.0049 (9)
C23	0.0338 (15)	0.0235 (14)	0.0329 (15)	0.0146 (12)	0.0136 (13)	0.0086 (12)
C21	0.0301 (15)	0.0256 (14)	0.0349 (16)	0.0116 (12)	0.0078 (13)	0.0052 (12)
C24	0.0334 (15)	0.0361 (16)	0.0350 (16)	0.0191 (13)	0.0152 (13)	0.0153 (13)
C22	0.0344 (16)	0.0339 (16)	0.0395 (17)	0.0158 (13)	0.0142 (14)	0.0086 (13)
O1	0.0247 (10)	0.0354 (12)	0.0463 (13)	0.0095 (9)	0.0047 (10)	0.0092 (10)
O2	0.0670 (16)	0.0607 (15)	0.0265 (11)	0.0464 (13)	0.0133 (11)	0.0121 (10)

Cu1—N1	2.052 (2)	C14—C15	1.410 (4)
Cu1—N2	2.106 (2)	C14—H14	0.9500
Cu1—O2	1.965 (2)	C15—C16	1.360 (5)
Cu1—Cl1	2.6190 (7)	C15—H15	0.9500
Cu1—Cl2	2.2272 (8)	C16—C17	1.417 (4)
C1—C10	1.374 (4)	C16—H16	0.9500
C1—C2	1.419 (4)	C17—C18	1.407 (4)
C1—N1	1.447 (3)	C18—C19	1.353 (4)
C2—C3	1.359 (4)	C18—H18	0.9500
C2—H2	0.9500	C19—C20	1.419 (4)
C3—C4	1.413 (4)	C19—H19	0.9500
C3—H3	0.9500	C20—N2	1.435 (3)
C4—C5	1.417 (4)	N1—C21	1.486 (3)
C4—C9	1.420 (4)	N1—H1	0.9300
C5—C6	1.361 (5)	N2—C23	1.497 (3)
C5—H5	0.9500	N2—H2A	0.9300
C6—C7	1.413 (4)	C23—C24	1.499 (4)
C6—H6	0.9500	C23—H23A	0.9900
C7—C8	1.357 (4)	C23—H23B	0.9900
C7—H7	0.9500	C21—C22	1.511 (4)
C8—C9	1.414 (4)	C21—H21A	0.9900
C8—H8	0.9500	C21—H21B	0.9900
C9—C10	1.430 (4)	C24—O2	1.430 (4)
C10—C11	1.509 (3)	C24—H24A	0.9900
C11—C20	1.385 (4)	C24—H24B	0.9900
C11—C12	1.431 (4)	C22—O1	1.420 (4)
C12—C13	1.417 (4)	C22—H22A	0.9900
C12—C17	1.428 (4)	C22—H22B	0.9900
C13—C14	1.368 (4)	O1—H1A	0.8400
C13—H13	0.9500	O2—H2B	0.8400
O2—Cu1—N1	165.49 (10)	C15—C16—C17	121.4 (3)
O2—Cu1—N2	79.76 (9)	C15—C16—H16	119.3
N1—Cu1—N2	91.66 (8)	C17—C16—H16	119.3
O2—Cu1—Cl2	88.68 (7)	C18—C17—C16	121.8 (3)
N1—Cu1—Cl2	96.06 (7)	C18—C17—C12	118.8 (2)
N2—Cu1—Cl2	160.29 (7)	C16—C17—C12	119.3 (3)
O2—Cu1—Cl1	97.74 (8)	C19—C18—C17	121.8 (2)
N1—Cu1—Cl1	93.68 (6)	C19—C18—H18	119.1
N2—Cu1—Cl1	88.52 (6)	C17—C18—H18	119.1
Cl2—Cu1—Cl1	108.97 (3)	C18—C19—C20	120.2 (3)
C10—C1—C2	121.2 (2)	C18—C19—H19	119.9
C10—C1—N1	119.5 (2)	C20—C19—H19	119.9
C2—C1—N1	119.2 (2)	C11—C20—C19	120.4 (2)
C3—C2—C1	120.1 (3)	C11—C20—N2	119.2 (2)
C3—C2—H2	120.0	C19—C20—N2	120.3 (2)
C1—C2—H2	120.0	C1—N1—C21	114.2 (2)
C2—C3—C4	121.1 (3)	C1—N1—Cu1	105.29 (16)
C2—C3—H3	119.4	C21—N1—Cu1	120.05 (18)
C4—C3—H3	119.4	C1—N1—H1	105.4
C3—C4—C5	121.8 (3)	C21—N1—H1	105.4
C3—C4—C9	118.8 (2)	Cu1—N1—H1	105.4
C5—C4—C9	119.4 (3)	C20—N2—C23	116.3 (2)
C6—C5—C4	121.1 (3)	C20—N2—Cu1	117.44 (16)
C6—C5—H5	119.4	C23—N2—Cu1	104.06 (16)
C4—C5—H5	119.4	C20—N2—H2A	106.0
C5—C6—C7	119.4 (3)	C23—N2—H2A	106.0
C5—C6—H6	120.3	Cu1—N2—H2A	106.0
C7—C6—H6	120.3	N2—C23—C24	108.1 (2)
C8—C7—C6	120.9 (3)	N2—C23—H23A	110.1
C8—C7—H7	119.6	C24—C23—H23A	110.1
C6—C7—H7	119.6	N2—C23—H23B	110.1
C7—C8—C9	121.3 (3)	C24—C23—H23B	110.1
C7—C8—H8	119.3	H23A—C23—H23B	108.4
C9—C8—H8	119.3	N1—C21—C22	112.1 (2)
C8—C9—C4	117.9 (2)	N1—C21—H21A	109.2
C8—C9—C10	122.3 (2)	C22—C21—H21A	109.2
C4—C9—C10	119.8 (2)	N1—C21—H21B	109.2
C1—C10—C9	118.9 (2)	C22—C21—H21B	109.2
C1—C10—C11	119.4 (2)	H21A—C21—H21B	107.9
C9—C10—C11	121.7 (2)	O2—C24—C23	106.1 (2)
C20—C11—C12	119.6 (2)	O2—C24—H24A	110.5
C20—C11—C10	119.7 (2)	C23—C24—H24A	110.5
C12—C11—C10	120.7 (2)	O2—C24—H24B	110.5
C13—C12—C17	117.7 (2)	C23—C24—H24B	110.5
C13—C12—C11	123.2 (2)	H24A—C24—H24B	108.7
C17—C12—C11	119.1 (2)	O1—C22—C21	112.1 (2)
C14—C13—C12	121.2 (3)	O1—C22—H22A	109.2
C14—C13—H13	119.4	C21—C22—H22A	109.2
C12—C13—H13	119.4	O1—C22—H22B	109.2
C13—C14—C15	120.8 (3)	C21—C22—H22B	109.2
C13—C14—H14	119.6	H22A—C22—H22B	107.9
C15—C14—H14	119.6	C22—O1—H1A	109.5
C16—C15—C14	119.5 (3)	C24—O2—Cu1	118.73 (18)
C16—C15—H15	120.2	C24—O2—H2B	109.5
C14—C15—H15	120.2	Cu1—O2—H2B	126.1
C10—C1—C2—C3	−0.9 (4)	C12—C17—C18—C19	2.1 (4)
N1—C1—C2—C3	−177.5 (3)	C17—C18—C19—C20	−0.7 (4)
C1—C2—C3—C4	1.4 (5)	C12—C11—C20—C19	1.8 (4)
C2—C3—C4—C5	179.2 (3)	C10—C11—C20—C19	−175.5 (2)
C2—C3—C4—C9	0.0 (4)	C12—C11—C20—N2	179.8 (2)
C3—C4—C5—C6	−178.4 (3)	C10—C11—C20—N2	2.6 (4)
C9—C4—C5—C6	0.8 (4)	C18—C19—C20—C11	−1.3 (4)
C4—C5—C6—C7	0.7 (5)	C18—C19—C20—N2	−179.3 (2)
C5—C6—C7—C8	−1.2 (5)	C10—C1—N1—C21	141.6 (3)
C6—C7—C8—C9	0.2 (5)	C2—C1—N1—C21	−41.7 (3)
C7—C8—C9—C4	1.3 (4)	C10—C1—N1—Cu1	−84.7 (2)
C7—C8—C9—C10	−179.4 (3)	C2—C1—N1—Cu1	92.0 (3)
C3—C4—C9—C8	177.4 (3)	O2—Cu1—N1—C1	6.6 (4)
C5—C4—C9—C8	−1.8 (4)	N2—Cu1—N1—C1	59.88 (16)
C3—C4—C9—C10	−1.8 (4)	Cl2—Cu1—N1—C1	−101.97 (15)
C5—C4—C9—C10	179.0 (2)	Cl1—Cu1—N1—C1	148.49 (15)
C2—C1—C10—C9	−1.0 (4)	O2—Cu1—N1—C21	137.0 (3)
N1—C1—C10—C9	175.7 (2)	N2—Cu1—N1—C21	−169.67 (19)
C2—C1—C10—C11	179.9 (2)	Cl2—Cu1—N1—C21	28.49 (19)
N1—C1—C10—C11	−3.5 (4)	Cl1—Cu1—N1—C21	−81.05 (19)
C8—C9—C10—C1	−176.9 (2)	C11—C20—N2—C23	163.4 (2)
C4—C9—C10—C1	2.3 (4)	C19—C20—N2—C23	−18.6 (3)
C8—C9—C10—C11	2.2 (4)	C11—C20—N2—Cu1	−72.4 (3)
C4—C9—C10—C11	−178.5 (2)	C19—C20—N2—Cu1	105.6 (2)
C1—C10—C11—C20	66.2 (3)	O2—Cu1—N2—C20	−160.18 (19)
C9—C10—C11—C20	−112.9 (3)	N1—Cu1—N2—C20	31.60 (18)
C1—C10—C11—C12	−111.0 (3)	Cl2—Cu1—N2—C20	144.81 (17)
C9—C10—C11—C12	69.9 (3)	Cl1—Cu1—N2—C20	−62.04 (17)
C20—C11—C12—C13	−180.0 (3)	O2—Cu1—N2—C23	−30.02 (17)
C10—C11—C12—C13	−2.8 (4)	N1—Cu1—N2—C23	161.76 (17)
C20—C11—C12—C17	−0.4 (4)	Cl2—Cu1—N2—C23	−85.0 (2)
C10—C11—C12—C17	176.8 (2)	Cl1—Cu1—N2—C23	68.12 (16)
C17—C12—C13—C14	0.1 (4)	C20—N2—C23—C24	−178.8 (2)
C11—C12—C13—C14	179.7 (3)	Cu1—N2—C23—C24	50.4 (2)
C12—C13—C14—C15	0.1 (5)	C1—N1—C21—C22	−174.3 (2)
C13—C14—C15—C16	−0.1 (5)	Cu1—N1—C21—C22	59.3 (3)
C14—C15—C16—C17	0.0 (4)	N2—C23—C24—O2	−47.2 (3)
C15—C16—C17—C18	−178.1 (3)	N1—C21—C22—O1	55.6 (3)
C15—C16—C17—C12	0.2 (4)	C23—C24—O2—Cu1	21.4 (3)
C13—C12—C17—C18	178.1 (3)	N1—Cu1—O2—C24	59.7 (5)
C11—C12—C17—C18	−1.5 (4)	N2—Cu1—O2—C24	5.2 (2)
C13—C12—C17—C16	−0.3 (4)	Cl2—Cu1—O2—C24	169.1 (2)
C11—C12—C17—C16	−179.9 (2)	Cl1—Cu1—O2—C24	−81.9 (2)
C16—C17—C18—C19	−179.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cl1	0.84	2.41	3.039 (2)	132
O2—H2B···Cl1i	0.84	2.33	2.996 (2)	137
N2—H2A···O1ii	0.93	2.00	2.889 (3)	158

Table 1

Selected bond lengths (Å)

Cu1—N1	2.052 (2)
Cu1—N2	2.106 (2)
Cu1—O2	1.965 (2)
Cu1—Cl1	2.6190 (7)
Cu1—Cl2	2.2272 (8)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯Cl1	0.84	2.41	3.039 (2)	132
O2—H2B⋯Cl1i	0.84	2.33	2.996 (2)	137
N2—H2A⋯O1ii	0.93	2.00	2.889 (3)	158

Symmetry codes: (i) ; (ii) .