[2,2′-(1,1′-Binaphthyl-2,2′-diyldiimino)­diethanol-κ3N,N′,O]dichloridocopper(II)

Huang, W.-Y.; Liu, D.-C.; Wei, H.-C.; Liang, F.-P.

doi:10.1107/S1600536811049828

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1844

https://doi.org/10.1107/S1600536811049828

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[2,2′-(1,1′-Binaphthyl-2,2′-diyldiimino)diethanol-κ³N,N′,O]dichloridocopper(II)

Wan-Yun Huang,^a Dong-Cheng Liu,^a Han-Chang Wei ^a and Fu-Pei Liang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Guangxi Normal University, Yucai Road 15, Guilin 541004, People's Republic of China
^*Correspondence e-mail: fliangoffice@yahoo.com

(Received 19 November 2011; accepted 21 November 2011; online 25 November 2011)

In the title complex, [CuCl₂(C₂₄H₂₄N₂O₂)], 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 uncoordinated hydroxy group links with a coordinated chloride anion via an intramolecular O—H⋯Cl hydrogen bond. Intermolecular 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_r = 506.89
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.107
S = 1.04
3758 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.40 e Å⁻³

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) -x+1, -y+1, -z+1; (ii) x-1, y, z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811049828/xu5393sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049828/xu5393Isup2.hkl

checkCIF report

Comment top

N-substituted diethanolamine ligands have been proven to be fruitful in the construction of fascinating functional metal complexes (Saalfrank et al., 2008; Ferguson et al., 2011; Alley et al., 2008). But the ligand which contains two or more N-substituted diethanolamine has received much less attention. we designed and synthesized successfully a racemic ligand of N, N'-Bis-(2-hydroxy-ethyl)-(1,1'-Binaphthyl-2,2'-diamine) (BHEBA), herein we report the crystal structure of a Cu^II complex about it. The single-crystal X-ray structural analysis reveals that asymmetric unit contains one five-coordinated Cu^II ion, a new ligand N,N'-(2-hydroxy-ethyl)-(1,1'-binaphthyl-2,2'-diamine) (HEBA), namely partly decomposed of the parent ligand and two Cl^- ions as shown in Fig. 1. Due to the Jahn-Teller effect, the distance of the Cu—Cl(1) bond is elongated to 2.6188 (Å), which is consistent with the reported copper complexes (Telfer et al., 2004). Two adjacent polymeric H-bonded chains of opposite chirality (Thob et al., 2010) by the hydrogen bond N(2)—H(2 A)···O(1) and O(1)—H (1 A)···Cl(1) extend along a direction, and these chains are interconnected by the repeating weak O(2)—H(2B)···Cl(1) (symmetry code: -x + 1, -y + 1, -z + 1) hydrogen bonds (Fig. 2.), which further stabilize the structure. The corresponding lengths and angles of hydrogen bonds are listed in Table 1.

Related literature top

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 top

The target ligand of racemic N,N'-Bis-(2-hydroxy-ethyl)-(1,1'-Binaphthyl-2,2'- diamine) (BHEBA) were synthesized by the reported procedure (Yan et al., 2008) in 55% yield using racemic 1,1'-binaphthyl-2,2'-diamine as materials.

CuCl₂ (25.5 mg, 0.15 mmol), NMe₄OH 18.1 mg (0.10 mmol), and BHEBA (46.1 mg, 0.10 mmol) were mixed in a CH₃OH /ⁱPrOH (10 ml, v/v 3:2) solution with vigorous stirring for 10 h. The resulting solution was filtered and left to stand at room temperature. Brown block crystals suitable for X-ray analysis were obtained in 30% yield by slow evaporation of the solvent over a period of two week. Analysis, calculated for C₂₄H₂₄N₂O₂Cl₂Cu: C 56.86, H 4.77, N 5.53%; found: C 56.45, H 4.43, N 5.62%.

Structure description top

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).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-numbering scheme and 30% displacement ellipsoids. H atoms of the Aryl group are omitted for clarity.
	Fig. 2. Two adjacent polymeric H-bonded chains of opposite chirality in the crystal structure, viewed along the a direction. H atoms of the Aryl group are omitted for clarity. Hydrogen bonds are shown as dashed lines. [Symmetry codes: (i) x - 1, y, z; (ii) -x + 1, -y + 1, -z + 1].

[2,2'-(1,1'-Binaphthyl-2,2'-diyldiimino)diethanol- κ³N,N',O]dichloridocopper(II) top

Crystal data top

[CuCl₂(C₂₄H₂₄N₂O₂)]	Z = 2
M_r = 506.89	F(000) = 522
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.070P)² + 0.7465P] where P = (F_o² + 2F_c²)/3
3758 reflections	(Δ/σ)_max = 0.001
280 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

[CuCl₂(C₂₄H₂₄N₂O₂)]	γ = 106.912 (2)°
M_r = 506.89	V = 1090.1 (2) Å³
Triclinic, P1	Z = 2
a = 7.4816 (8) Å	Mo Kα radiation
b = 10.4211 (11) Å	µ = 1.27 mm⁻¹
c = 15.2116 (16) Å	T = 185 K
α = 94.130 (2)°	0.31 × 0.17 × 0.10 mm
β = 103.633 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3758 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3363 reflections with I > 2σ(I)
T_min = 0.694, T_max = 0.883	R_int = 0.012
5452 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.04	Δρ_max = 0.53 e Å⁻³
3758 reflections	Δρ_min = −0.40 e Å⁻³
280 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[CuCl₂(C₂₄H₂₄N₂O₂)]
M_r	506.89
Crystal system, space group	Triclinic, P1
Temperature (K)	185
a, b, c (Å)	7.4816 (8), 10.4211 (11), 15.2116 (16)
α, β, γ (°)	94.130 (2), 103.633 (2), 106.912 (2)
V (Å³)	1090.1 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.27
Crystal size (mm)	0.31 × 0.17 × 0.10

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.694, 0.883
No. of measured, independent and observed [I > 2σ(I)] reflections	5452, 3758, 3363
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.107, 1.04
No. of reflections	3758
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.40

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1; (ii) x−1, y, z.

Acknowledgements

The authors thank the National Natural Science Foundation of China (grant No. 20971029) and the Guangxi Natural Science Foundation of China (No. 2010GXNSFD013018).

References

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