metal-organic compounds
Poly[bis[chloridocopper(I)]-μ4-1,4-bis[1-(3-pyridylmethyl)-1H-benzimidazol-2-yl]butane]
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
The title CuI 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 CuI cation is three-coordinated by a ClN2 donor set. The anion acts as a tetradentate ligand, linking CuI 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
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Refinement
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Data collection: SMART (Bruker, 1999); cell 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
10.1107/S1600536808008696/bt2684sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808008696/bt2684Isup2.hkl
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.
All H-atoms bound to carbon were refined using a riding model with d(C—H) = 0.93 Å, Uiso=1.2Ueq (C) for aromatic and 0.97 Å, Uiso = 1.5Ueq (C) for CH2 atoms.
Data collection: SMART (Bruker, 1999); cell
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).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.] |
[Cu2Cl2(C30H28N6)] | F(000) = 1368 |
Mr = 670.56 | Dx = 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 |
Bruker APEX CCD area-detector diffractometer | 6759 independent reflections |
Radiation source: fine-focus sealed tube | 3170 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
ω scans | θmax = 28.3°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→12 |
Tmin = 0.66, Tmax = 0.84 | k = −19→23 |
17514 measured reflections | l = −22→22 |
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(Fo2) + (0.0872P)2] where P = (Fo2 + 2Fc2)/3 |
6759 reflections | (Δ/σ)max = 0.001 |
361 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
[Cu2Cl2(C30H28N6)] | V = 2900.5 (6) Å3 |
Mr = 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)° |
Bruker APEX CCD area-detector diffractometer | 6759 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3170 reflections with I > 2σ(I) |
Tmin = 0.66, Tmax = 0.84 | Rint = 0.062 |
17514 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.186 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.42 e Å−3 |
6759 reflections | Δρmin = −0.44 e Å−3 |
361 parameters |
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 | 0.74531 (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) |
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) |
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)] |
Mr | 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) |
Tmin, Tmax | 0.66, 0.84 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17514, 6759, 3170 |
Rint | 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 |
Δρmax, Δρmin (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).
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
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As shown in Fig. 1, three are two crystallographically unique Cu ions, and each CuI ion is three-coordinated by one Cl- anion and two nitrogen atoms from two L anions. Each L anion in (I) coordinates to four CuI cations through its two imidazole N atoms and two pyridine N atoms, thus acing as a tetradentate ligand. The CuI cations are linked by L anions to form a chain along a axis. For a related compound, see Wang & Xu (2007).