Poly[bis­[chlorido­cop­per(I)]-μ4-1,4-bis­[1-(3-pyridylmeth­yl)-1H-benzimid­azol-2-yl]butane]

Zhang, W.-P.; Liu, Y.-Y.; Ma, J.-F.

doi:10.1107/S1600536808008696

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page m641

doi:10.1107/S1600536808008696

Open

access

Poly[bis[chloridocopper(I)]-μ₄-1,4-bis[1-(3-pyridylmethyl)-1H-benzimidazol-2-yl]butane]

Wei-Ping Zhang,^a,^b Ying-Ying Liu ^a and Jian-Fang Ma ^a ^*

^aDepartment of Chemistry, Northeast Normal University, Changchun 130024, People's Republic of China, and ^bJilin Medical College, Jilin 132013, People's Republic of China
^*Correspondence e-mail: majf247nenu@yahoo.com.cn

(Received 12 March 2008; accepted 1 April 2008; online 10 April 2008)

The title Cu^I coordination polymer, [Cu₂Cl₂(C₃₀H₂₈N₆)]_n, was obtained by reaction of CuCl₂·2H₂O and 1,4-bis[1-(3-pyridylmethyl)-1H-benzimidazol-2-yl]butane. Each Cu^I cation is three-coordinated by a ClN₂ donor set. The anion acts as a tetradentate ligand, linking Cu^I centres into a polymeric chain.

Related literature

For a related compound, see Wang & Xu (2007 ). For details of the synthesis, see: Li et al. (2007 ).

Experimental

Crystal data

[Cu₂Cl₂(C₃₀H₂₈N₆)]
M_r = 670.56
Monoclinic, P 2₁ /n
a = 9.4792 (11) Å
b = 17.810 (2) Å
c = 17.326 (2) Å
β = 97.412 (2)°
V = 2900.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.68 mm⁻¹
T = 293 (2) K
0.23 × 0.20 × 0.09 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.66, T_max = 0.84
17514 measured reflections
6759 independent reflections
3170 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.185
S = 0.97
6759 reflections
361 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cu1—N4	1.940 (4)
Cu1—N6ⁱ	2.079 (5)
Cu1—Cl1	2.1836 (16)
Cu2—N1	1.942 (4)
Cu2—N5ⁱⁱ	2.116 (4)
Cu2—Cl2	2.1672 (16)

N4—Cu1—N6ⁱ	111.23 (18)
N4—Cu1—Cl1	141.19 (13)
N6ⁱ—Cu1—Cl1	107.12 (13)
N1—Cu2—N5ⁱⁱ	108.71 (17)
N1—Cu2—Cl2	142.93 (13)
N5ⁱⁱ—Cu2—Cl2	107.36 (13)
Symmetry codes: (i) -x+2, -y+2, -z; (ii) -x+1, -y+2, -z.

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808008696/bt2684sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008696/bt2684Isup2.hkl

checkCIF report

Comment top

As shown in Fig. 1, three are two crystallographically unique Cu ions, and each Cu^I ion is three-coordinated by one Cl^- anion and two nitrogen atoms from two L anions. Each L anion in (I) coordinates to four Cu^I cations through its two imidazole N atoms and two pyridine N atoms, thus acing as a tetradentate ligand. The Cu^I cations are linked by L anions to form a chain along a axis. For a related compound, see Wang & Xu (2007).

Related literature top

For a related compound, see Wang & Xu (2007). For details of the synthesis, see: Li et al. (2007).

Experimental top

The ligand was synthesized according to the literature (Li et al., 2007) but 4-(chloromethyl)pyridine was replaced by 3-(chloromethyl)pyridine. A mixture of CuCl₂.2H₂O (0.034 g, 2 mmol), H₂L (0.945 g, 2 mmol), and water (8 ml) was sealed in a Teflon reactor (15 ml) and heated at 130 °C for 3 days. After the mixture had been cooled to room temperature at 10 °C.h^-1, red crystals of the title compound were obtained.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) -x + 2, -y + 2, -z; (ii) -x + 1, -y + 2, -z.]

poly[bis[chloridocopper(I)]-µ₄- 1,4-bis[1-(3-pyridylmethyl)-1H-benzimidazol-2-yl]butane] top

Crystal data top

[Cu₂Cl₂(C₃₀H₂₈N₆)]	F(000) = 1368
M_r = 670.56	D_x = 1.536 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3170 reflections
a = 9.4792 (11) Å	θ = 1.7–28.3°
b = 17.810 (2) Å	µ = 1.68 mm⁻¹
c = 17.326 (2) Å	T = 293 K
β = 97.412 (2)°	Block, red
V = 2900.5 (6) Å³	0.23 × 0.20 × 0.09 mm
Z = 4

Data collection top

Bruker APEX CCD area-detector diffractometer	6759 independent reflections
Radiation source: fine-focus sealed tube	3170 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
ω scans	θ_max = 28.3°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
T_min = 0.66, T_max = 0.84	k = −19→23
17514 measured reflections	l = −22→22

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.186	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0872P)²] where P = (F_o² + 2F_c²)/3
6759 reflections	(Δ/σ)_max = 0.001
361 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

[Cu₂Cl₂(C₃₀H₂₈N₆)]	V = 2900.5 (6) Å³
M_r = 670.56	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.4792 (11) Å	µ = 1.68 mm⁻¹
b = 17.810 (2) Å	T = 293 K
c = 17.326 (2) Å	0.23 × 0.20 × 0.09 mm
β = 97.412 (2)°

Data collection top

Bruker APEX CCD area-detector diffractometer	6759 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3170 reflections with I > 2σ(I)
T_min = 0.66, T_max = 0.84	R_int = 0.062
17514 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.186	H-atom parameters constrained
S = 0.97	Δρ_max = 0.42 e Å⁻³
6759 reflections	Δρ_min = −0.44 e Å⁻³
361 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. 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	0.74531 (8)	0.80687 (4)	0.14462 (4)	0.0609 (2)
Cu2	0.78422 (7)	0.87957 (4)	−0.16694 (4)	0.0574 (2)
C1	0.7866 (5)	0.9707 (3)	0.1746 (3)	0.0456 (12)
C2	0.7040 (5)	0.9140 (3)	0.2683 (3)	0.0460 (12)
C3	0.7232 (5)	0.9888 (3)	0.2904 (3)	0.0474 (12)
C4	0.6930 (6)	1.0155 (4)	0.3612 (3)	0.0660 (16)
H4	0.7093	1.0652	0.3764	0.079*
C5	0.6365 (7)	0.9631 (4)	0.4082 (3)	0.083 (2)
H5	0.6131	0.9783	0.4563	0.099*
C6	0.6141 (7)	0.8894 (4)	0.3856 (3)	0.081 (2)
H6	0.5730	0.8567	0.4181	0.097*
C7	0.6507 (6)	0.8627 (3)	0.3163 (3)	0.0646 (16)
H7	0.6399	0.8123	0.3026	0.078*
C8	0.8373 (6)	0.9869 (3)	0.0976 (3)	0.0552 (14)
H8A	0.8916	0.9442	0.0828	0.066*
H8B	0.9003	1.0300	0.1033	0.066*
C9	0.7150 (5)	1.0027 (3)	0.0326 (3)	0.0493 (12)
H9A	0.6547	0.9587	0.0243	0.059*
H9B	0.6577	1.0438	0.0479	0.059*
C10	0.7729 (5)	1.0226 (3)	−0.0425 (3)	0.0581 (14)
H10A	0.8318	0.9817	−0.0568	0.070*
H10B	0.8325	1.0669	−0.0338	0.070*
C11	0.6556 (6)	1.0379 (3)	−0.1096 (3)	0.0559 (14)
H11A	0.5821	1.0000	−0.1093	0.067*
H11B	0.6130	1.0863	−0.1016	0.067*
C12	0.7078 (5)	1.0375 (3)	−0.1868 (3)	0.0466 (12)
C13	0.8090 (5)	1.0002 (3)	−0.2879 (3)	0.0452 (12)
C14	0.7697 (5)	1.0753 (3)	−0.3012 (3)	0.0499 (13)
C15	0.7930 (7)	1.1126 (3)	−0.3687 (3)	0.0685 (17)
H15	0.7635	1.1619	−0.3781	0.082*
C16	0.8612 (8)	1.0735 (4)	−0.4208 (4)	0.082 (2)
H16	0.8805	1.0972	−0.4661	0.099*
C17	0.9024 (7)	0.9993 (4)	−0.4079 (3)	0.0748 (19)
H17	0.9484	0.9745	−0.4447	0.090*
C18	0.8765 (6)	0.9618 (3)	−0.3416 (3)	0.0589 (14)
H18	0.9038	0.9119	−0.3334	0.071*
C19	0.6695 (6)	1.1750 (3)	−0.2180 (3)	0.0558 (14)
H19A	0.5894	1.1755	−0.1883	0.067*
H19B	0.6417	1.2019	−0.2663	0.067*
C20	0.7944 (6)	1.2145 (3)	−0.1722 (3)	0.0521 (13)
C21	0.7711 (7)	1.2767 (4)	−0.1289 (4)	0.0792 (19)
H21	0.6790	1.2932	−0.1258	0.095*
C22	0.8856 (9)	1.3143 (4)	−0.0902 (4)	0.095 (2)
H22	0.8707	1.3572	−0.0617	0.114*
C23	1.0253 (7)	1.2885 (4)	−0.0931 (4)	0.0750 (18)
H23	1.1017	1.3144	−0.0664	0.090*
C24	0.9395 (6)	1.1933 (3)	−0.1734 (3)	0.0620 (15)
H24	0.9582	1.1526	−0.2042	0.074*
C25	0.7993 (5)	1.1051 (3)	0.2233 (3)	0.0497 (13)
H25A	0.8834	1.1140	0.1981	0.060*
H25B	0.8160	1.1266	0.2751	0.060*
C26	0.6735 (5)	1.1438 (3)	0.1775 (3)	0.0447 (12)
C27	0.6887 (6)	1.1899 (3)	0.1157 (3)	0.0600 (15)
H27	0.7789	1.2003	0.1027	0.072*
C28	0.5706 (6)	1.2209 (4)	0.0727 (4)	0.0742 (18)
H28	0.5800	1.2532	0.0315	0.089*
C29	0.4405 (6)	1.2033 (3)	0.0918 (3)	0.0619 (15)
H29	0.3606	1.2231	0.0619	0.074*
C30	0.5386 (6)	1.1306 (3)	0.1931 (3)	0.0533 (13)
H30	0.5270	1.0999	0.2352	0.064*
N1	0.7676 (4)	0.9779 (2)	−0.2158 (2)	0.0484 (10)
N2	0.7044 (4)	1.0974 (2)	−0.2354 (2)	0.0491 (11)
N3	0.7773 (4)	1.0246 (2)	0.2295 (2)	0.0459 (10)
N4	0.7451 (4)	0.9039 (2)	0.1955 (2)	0.0489 (10)
N5	0.4217 (5)	1.1587 (3)	0.1516 (3)	0.0584 (12)
N6	1.0488 (5)	1.2277 (2)	−0.1335 (3)	0.0610 (12)
Cl1	0.60349 (16)	0.71402 (8)	0.10540 (9)	0.0659 (4)
Cl2	0.93594 (16)	0.80208 (9)	−0.10598 (10)	0.0758 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0632 (5)	0.0542 (4)	0.0644 (5)	0.0018 (3)	0.0055 (4)	−0.0063 (3)
Cu2	0.0579 (5)	0.0523 (4)	0.0641 (4)	0.0078 (3)	0.0158 (3)	0.0094 (3)
C1	0.033 (3)	0.057 (3)	0.047 (3)	0.005 (2)	0.007 (2)	0.002 (3)
C2	0.040 (3)	0.050 (3)	0.049 (3)	0.002 (2)	0.007 (2)	0.008 (2)
C3	0.048 (3)	0.057 (3)	0.038 (3)	−0.005 (2)	0.007 (2)	0.002 (2)
C4	0.074 (4)	0.071 (4)	0.053 (3)	−0.007 (3)	0.009 (3)	−0.007 (3)
C5	0.100 (5)	0.105 (6)	0.047 (3)	−0.014 (4)	0.019 (3)	−0.004 (4)
C6	0.098 (6)	0.088 (5)	0.058 (4)	−0.019 (4)	0.014 (4)	0.017 (4)
C7	0.071 (4)	0.059 (4)	0.062 (4)	−0.011 (3)	0.000 (3)	0.001 (3)
C8	0.053 (3)	0.061 (3)	0.053 (3)	−0.002 (3)	0.013 (3)	−0.002 (3)
C9	0.049 (3)	0.059 (3)	0.040 (3)	−0.002 (3)	0.007 (2)	0.000 (2)
C10	0.051 (3)	0.076 (4)	0.051 (3)	−0.004 (3)	0.018 (3)	−0.003 (3)
C11	0.058 (4)	0.065 (4)	0.047 (3)	0.006 (3)	0.016 (3)	0.001 (3)
C12	0.043 (3)	0.051 (3)	0.046 (3)	0.000 (2)	0.008 (2)	0.003 (2)
C13	0.039 (3)	0.054 (3)	0.043 (3)	−0.005 (2)	0.008 (2)	0.000 (2)
C14	0.047 (3)	0.051 (3)	0.053 (3)	−0.002 (2)	0.011 (3)	0.001 (2)
C15	0.075 (4)	0.066 (4)	0.069 (4)	0.004 (3)	0.022 (3)	0.021 (3)
C16	0.110 (6)	0.084 (5)	0.059 (4)	0.009 (4)	0.033 (4)	0.025 (3)
C17	0.088 (5)	0.091 (5)	0.051 (3)	0.003 (4)	0.032 (3)	0.001 (3)
C18	0.058 (4)	0.059 (4)	0.061 (3)	0.004 (3)	0.012 (3)	−0.010 (3)
C19	0.052 (3)	0.047 (3)	0.067 (4)	0.007 (3)	0.005 (3)	−0.002 (3)
C20	0.060 (4)	0.044 (3)	0.052 (3)	0.007 (3)	0.004 (3)	0.001 (2)
C21	0.064 (4)	0.075 (4)	0.100 (5)	0.004 (3)	0.014 (4)	−0.025 (4)
C22	0.105 (6)	0.076 (5)	0.101 (5)	0.026 (4)	0.002 (5)	−0.041 (4)
C23	0.067 (4)	0.069 (4)	0.088 (5)	−0.002 (3)	0.004 (4)	−0.016 (4)
C24	0.054 (4)	0.055 (3)	0.079 (4)	0.005 (3)	0.016 (3)	−0.017 (3)
C25	0.050 (3)	0.048 (3)	0.050 (3)	−0.005 (2)	0.005 (3)	0.001 (2)
C26	0.045 (3)	0.039 (3)	0.050 (3)	−0.001 (2)	0.007 (2)	−0.005 (2)
C27	0.048 (3)	0.060 (4)	0.073 (4)	−0.002 (3)	0.014 (3)	0.012 (3)
C28	0.053 (4)	0.086 (4)	0.084 (4)	−0.003 (3)	0.007 (3)	0.039 (4)
C29	0.048 (4)	0.061 (4)	0.077 (4)	0.005 (3)	0.009 (3)	0.020 (3)
C30	0.050 (4)	0.054 (3)	0.058 (3)	0.003 (3)	0.015 (3)	0.012 (3)
N1	0.053 (3)	0.047 (2)	0.046 (2)	0.001 (2)	0.008 (2)	0.003 (2)
N2	0.051 (3)	0.046 (3)	0.052 (3)	−0.001 (2)	0.014 (2)	0.000 (2)
N3	0.043 (3)	0.052 (3)	0.042 (2)	0.0028 (19)	0.0033 (19)	−0.002 (2)
N4	0.044 (3)	0.050 (3)	0.054 (3)	0.004 (2)	0.011 (2)	0.000 (2)
N5	0.054 (3)	0.057 (3)	0.065 (3)	0.008 (2)	0.011 (2)	0.013 (2)
N6	0.057 (3)	0.049 (3)	0.076 (3)	−0.002 (2)	0.008 (3)	−0.016 (2)
Cl1	0.0595 (9)	0.0634 (9)	0.0718 (9)	−0.0083 (7)	−0.0024 (7)	0.0051 (7)
Cl2	0.0494 (9)	0.0694 (10)	0.1084 (12)	0.0091 (7)	0.0093 (8)	0.0271 (9)

Geometric parameters (Å, º) top

Cu1—N4	1.940 (4)	C14—N2	1.423 (6)
Cu1—N6ⁱ	2.079 (5)	C15—C16	1.367 (8)
Cu1—Cl1	2.1836 (16)	C15—H15	0.9300
Cu2—N1	1.942 (4)	C16—C17	1.387 (8)
Cu2—N5ⁱⁱ	2.116 (4)	C16—H16	0.9300
Cu2—Cl2	2.1672 (16)	C17—C18	1.378 (7)
C1—N4	1.318 (6)	C17—H17	0.9300
C1—N3	1.363 (6)	C18—H18	0.9300
C1—C8	1.502 (7)	C19—N2	1.462 (6)
C2—C7	1.375 (7)	C19—C20	1.510 (7)
C2—N4	1.379 (6)	C19—H19A	0.9700
C2—C3	1.391 (7)	C19—H19B	0.9700
C3—C4	1.380 (7)	C20—C21	1.372 (8)
C3—N3	1.385 (6)	C20—C24	1.429 (7)
C4—C5	1.390 (8)	C21—C22	1.374 (9)
C4—H4	0.9300	C21—H21	0.9300
C5—C6	1.379 (8)	C22—C23	1.408 (9)
C5—H5	0.9300	C22—H22	0.9300
C6—C7	1.376 (8)	C23—N6	1.324 (7)
C6—H6	0.9300	C23—H23	0.9300
C7—H7	0.9300	C24—N6	1.319 (7)
C8—C9	1.535 (7)	C24—H24	0.9300
C8—H8A	0.9700	C25—N3	1.455 (6)
C8—H8B	0.9700	C25—C26	1.511 (7)
C9—C10	1.517 (6)	C25—H25A	0.9700
C9—H9A	0.9700	C25—H25B	0.9700
C9—H9B	0.9700	C26—C30	1.361 (7)
C10—C11	1.526 (7)	C26—C27	1.373 (7)
C10—H10A	0.9700	C27—C28	1.377 (8)
C10—H10B	0.9700	C27—H27	0.9300
C11—C12	1.485 (6)	C28—C29	1.355 (7)
C11—H11A	0.9700	C28—H28	0.9300
C11—H11B	0.9700	C29—N5	1.335 (6)
C12—N1	1.332 (6)	C29—H29	0.9300
C12—N2	1.357 (6)	C30—N5	1.338 (6)
C13—C18	1.379 (6)	C30—H30	0.9300
C13—C14	1.399 (7)	N5—Cu2ⁱⁱ	2.116 (4)
C13—N1	1.414 (6)	N6—Cu1ⁱ	2.079 (5)
C14—C15	1.387 (7)

N4—Cu1—N6ⁱ	111.23 (18)	C18—C17—C16	121.3 (5)
N4—Cu1—Cl1	141.19 (13)	C18—C17—H17	119.3
N6ⁱ—Cu1—Cl1	107.12 (13)	C16—C17—H17	119.3
N1—Cu2—N5ⁱⁱ	108.71 (17)	C17—C18—C13	118.0 (5)
N1—Cu2—Cl2	142.93 (13)	C17—C18—H18	121.0
N5ⁱⁱ—Cu2—Cl2	107.36 (13)	C13—C18—H18	121.0
N4—C1—N3	113.3 (4)	N2—C19—C20	111.4 (4)
N4—C1—C8	123.9 (5)	N2—C19—H19A	109.3
N3—C1—C8	122.8 (5)	C20—C19—H19A	109.3
C7—C2—N4	129.4 (5)	N2—C19—H19B	109.3
C7—C2—C3	121.1 (5)	C20—C19—H19B	109.3
N4—C2—C3	109.5 (4)	H19A—C19—H19B	108.0
C4—C3—N3	131.1 (5)	C21—C20—C24	116.3 (5)
C4—C3—C2	122.6 (5)	C21—C20—C19	119.5 (5)
N3—C3—C2	106.3 (4)	C24—C20—C19	124.1 (5)
C3—C4—C5	115.4 (6)	C20—C21—C22	119.2 (6)
C3—C4—H4	122.3	C20—C21—H21	120.4
C5—C4—H4	122.3	C22—C21—H21	120.4
C6—C5—C4	122.0 (6)	C21—C22—C23	120.7 (6)
C6—C5—H5	119.0	C21—C22—H22	119.7
C4—C5—H5	119.0	C23—C22—H22	119.7
C7—C6—C5	122.0 (6)	N6—C23—C22	120.6 (6)
C7—C6—H6	119.0	N6—C23—H23	119.7
C5—C6—H6	119.0	C22—C23—H23	119.7
C2—C7—C6	116.8 (5)	N6—C24—C20	124.2 (5)
C2—C7—H7	121.6	N6—C24—H24	117.9
C6—C7—H7	121.6	C20—C24—H24	117.9
C1—C8—C9	112.9 (4)	N3—C25—C26	112.2 (4)
C1—C8—H8A	109.0	N3—C25—H25A	109.2
C9—C8—H8A	109.0	C26—C25—H25A	109.2
C1—C8—H8B	109.0	N3—C25—H25B	109.2
C9—C8—H8B	109.0	C26—C25—H25B	109.2
H8A—C8—H8B	107.8	H25A—C25—H25B	107.9
C10—C9—C8	110.5 (4)	C30—C26—C27	117.0 (5)
C10—C9—H9A	109.5	C30—C26—C25	121.1 (5)
C8—C9—H9A	109.5	C27—C26—C25	121.8 (5)
C10—C9—H9B	109.5	C26—C27—C28	120.1 (5)
C8—C9—H9B	109.5	C26—C27—H27	120.0
H9A—C9—H9B	108.1	C28—C27—H27	120.0
C9—C10—C11	112.7 (4)	C29—C28—C27	118.6 (5)
C9—C10—H10A	109.0	C29—C28—H28	120.7
C11—C10—H10A	109.0	C27—C28—H28	120.7
C9—C10—H10B	109.0	N5—C29—C28	123.0 (5)
C11—C10—H10B	109.0	N5—C29—H29	118.5
H10A—C10—H10B	107.8	C28—C29—H29	118.5
C12—C11—C10	113.0 (4)	N5—C30—C26	124.3 (5)
C12—C11—H11A	109.0	N5—C30—H30	117.8
C10—C11—H11A	109.0	C26—C30—H30	117.8
C12—C11—H11B	109.0	C12—N1—C13	106.8 (4)
C10—C11—H11B	109.0	C12—N1—Cu2	124.7 (3)
H11A—C11—H11B	107.8	C13—N1—Cu2	128.5 (3)
N1—C12—N2	111.8 (4)	C12—N2—C14	107.5 (4)
N1—C12—C11	123.4 (4)	C12—N2—C19	127.1 (4)
N2—C12—C11	124.8 (5)	C14—N2—C19	124.1 (4)
C18—C13—C14	120.0 (5)	C1—N3—C3	105.7 (4)
C18—C13—N1	131.5 (5)	C1—N3—C25	128.3 (4)
C14—C13—N1	108.5 (4)	C3—N3—C25	125.5 (4)
C15—C14—C13	122.0 (5)	C1—N4—C2	105.2 (4)
C15—C14—N2	132.5 (5)	C1—N4—Cu1	131.3 (3)
C13—C14—N2	105.5 (4)	C2—N4—Cu1	123.3 (3)
C16—C15—C14	116.9 (5)	C29—N5—C30	117.0 (5)
C16—C15—H15	121.5	C29—N5—Cu2ⁱⁱ	120.4 (4)
C14—C15—H15	121.5	C30—N5—Cu2ⁱⁱ	121.7 (4)
C15—C16—C17	121.7 (5)	C24—N6—C23	118.9 (5)
C15—C16—H16	119.1	C24—N6—Cu1ⁱ	119.8 (4)
C17—C16—H16	119.1	C23—N6—Cu1ⁱ	121.0 (4)

C7—C2—C3—C4	1.2 (8)	C18—C13—N1—C12	179.1 (5)
N4—C2—C3—C4	−179.0 (5)	C14—C13—N1—C12	−0.9 (5)
C7—C2—C3—N3	−179.8 (5)	C18—C13—N1—Cu2	−3.1 (8)
N4—C2—C3—N3	0.0 (5)	C14—C13—N1—Cu2	176.9 (3)
N3—C3—C4—C5	178.9 (5)	N5ⁱⁱ—Cu2—N1—C12	57.7 (4)
C2—C3—C4—C5	−2.4 (8)	Cl2—Cu2—N1—C12	−108.5 (4)
C3—C4—C5—C6	0.8 (10)	N5ⁱⁱ—Cu2—N1—C13	−119.7 (4)
C4—C5—C6—C7	2.2 (11)	Cl2—Cu2—N1—C13	74.1 (5)
N4—C2—C7—C6	−178.0 (6)	N1—C12—N2—C14	−1.1 (6)
C3—C2—C7—C6	1.8 (8)	C11—C12—N2—C14	177.4 (5)
C5—C6—C7—C2	−3.4 (10)	N1—C12—N2—C19	−168.9 (5)
N4—C1—C8—C9	84.5 (6)	C11—C12—N2—C19	9.6 (8)
N3—C1—C8—C9	−94.6 (6)	C15—C14—N2—C12	178.7 (6)
C1—C8—C9—C10	177.0 (5)	C13—C14—N2—C12	0.5 (5)
C8—C9—C10—C11	179.2 (4)	C15—C14—N2—C19	−13.0 (9)
C9—C10—C11—C12	−164.8 (5)	C13—C14—N2—C19	168.7 (5)
C10—C11—C12—N1	61.0 (7)	C20—C19—N2—C12	79.5 (6)
C10—C11—C12—N2	−117.3 (6)	C20—C19—N2—C14	−86.5 (6)
C18—C13—C14—C15	1.8 (8)	N4—C1—N3—C3	−0.8 (5)
N1—C13—C14—C15	−178.2 (5)	C8—C1—N3—C3	178.3 (4)
C18—C13—C14—N2	−179.7 (4)	N4—C1—N3—C25	−173.0 (4)
N1—C13—C14—N2	0.2 (5)	C8—C1—N3—C25	6.2 (8)
C13—C14—C15—C16	−2.3 (9)	C4—C3—N3—C1	179.4 (6)
N2—C14—C15—C16	179.7 (6)	C2—C3—N3—C1	0.5 (5)
C14—C15—C16—C17	1.5 (10)	C4—C3—N3—C25	−8.2 (8)
C15—C16—C17—C18	−0.1 (11)	C2—C3—N3—C25	172.9 (4)
C16—C17—C18—C13	−0.5 (9)	C26—C25—N3—C1	77.3 (6)
C14—C13—C18—C17	−0.4 (8)	C26—C25—N3—C3	−93.5 (5)
N1—C13—C18—C17	179.7 (5)	N3—C1—N4—C2	0.8 (5)
N2—C19—C20—C21	−158.4 (5)	C8—C1—N4—C2	−178.4 (5)
N2—C19—C20—C24	24.6 (7)	N3—C1—N4—Cu1	−176.0 (3)
C24—C20—C21—C22	0.1 (9)	C8—C1—N4—Cu1	4.9 (7)
C19—C20—C21—C22	−177.1 (6)	C7—C2—N4—C1	179.3 (5)
C20—C21—C22—C23	−1.5 (11)	C3—C2—N4—C1	−0.4 (5)
C21—C22—C23—N6	0.3 (11)	C7—C2—N4—Cu1	−3.6 (7)
C21—C20—C24—N6	2.8 (9)	C3—C2—N4—Cu1	176.7 (3)
C19—C20—C24—N6	179.9 (5)	N6ⁱ—Cu1—N4—C1	63.3 (5)
N3—C25—C26—C30	48.3 (6)	Cl1—Cu1—N4—C1	−126.0 (4)
N3—C25—C26—C27	−127.6 (5)	N6ⁱ—Cu1—N4—C2	−113.0 (4)
C30—C26—C27—C28	0.4 (8)	Cl1—Cu1—N4—C2	57.7 (5)
C25—C26—C27—C28	176.4 (5)	C28—C29—N5—C30	−0.6 (9)
C26—C27—C28—C29	−1.6 (9)	C28—C29—N5—Cu2ⁱⁱ	−170.4 (5)
C27—C28—C29—N5	1.7 (10)	C26—C30—N5—C29	−0.7 (8)
C27—C26—C30—N5	0.8 (8)	C26—C30—N5—Cu2ⁱⁱ	169.0 (4)
C25—C26—C30—N5	−175.2 (5)	C20—C24—N6—C23	−4.1 (9)
N2—C12—N1—C13	1.2 (6)	C20—C24—N6—Cu1ⁱ	−177.5 (4)
C11—C12—N1—C13	−177.3 (5)	C22—C23—N6—C24	2.5 (9)
N2—C12—N1—Cu2	−176.7 (3)	C22—C23—N6—Cu1ⁱ	175.8 (5)
C11—C12—N1—Cu2	4.8 (7)

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

Experimental details

Crystal data
Chemical formula	[Cu₂Cl₂(C₃₀H₂₈N₆)]
M_r	670.56
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.4792 (11), 17.810 (2), 17.326 (2)
β (°)	97.412 (2)
V (Å³)	2900.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.68
Crystal size (mm)	0.23 × 0.20 × 0.09

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.66, 0.84
No. of measured, independent and observed [I > 2σ(I)] reflections	17514, 6759, 3170
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.186, 0.97
No. of reflections	6759
No. of parameters	361
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.44

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Cu1—N4	1.940 (4)	Cu2—N1	1.942 (4)
Cu1—N6ⁱ	2.079 (5)	Cu2—N5ⁱⁱ	2.116 (4)
Cu1—Cl1	2.1836 (16)	Cu2—Cl2	2.1672 (16)

N4—Cu1—N6ⁱ	111.23 (18)	N1—Cu2—N5ⁱⁱ	108.71 (17)
N4—Cu1—Cl1	141.19 (13)	N1—Cu2—Cl2	142.93 (13)
N6ⁱ—Cu1—Cl1	107.12 (13)	N5ⁱⁱ—Cu2—Cl2	107.36 (13)

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

Acknowledgements

We thank the Analysis and Testing Foundation of Northeast Normal University for support.

References

Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, S.-L., Liu, J. & Ma, J.-F. (2007). Acta Cryst. E63, o4509. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, W.-J. & Xu, L. (2007). Acta Cryst. E63, m1993–m1994. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.