Acta Cryst. (2012). E68, m999-m1000 [ doi:10.1107/S1600536812028462 ]
The asymmetric unit of the title compound, [Cu2(C18H14Cl4N2O2)2]n, contains two independent CuII ions which are bridged by a pair of 4,4',6,6'-tetrachloro-2,2'-[butane-1,4-diylbis(nitrilomethanylylidene)]diphenolate ligands, forming a dinuclear unit. One of the CuII ions is coordinated in a distorted square-planar environment and the other is coordinated in a distorted square-pyramidal environment. The long apical Cu-O bond of the square-pyramidal coordinated CuII ion is formed by a symmetry-related O atom, creating a one-dimensional polymer along [010]. In addition, short intermolecular ClCl distances [3.444 (2) Å] and weak
-
interactions [centroid-centroid distances = 3.736 (2)-3.875 (3) Å] are observed. The crystal studied was an inversion twin with a refined twin component ratio of 0.60 (1):0.40 (1).
The title complex was synthesized by an methanolic solution (50 ml) of bis(3,5-chlorosalicylaldeyde)-1,4-butanediimine (2 mmol) and CuCl2.4H2O (2 mmol). After stirring at reflux conditions for 2 h, the solution was filtered and the resulting dark-red powder was crystallized from DMF, giving single crystals suitable for X-ray diffraction.
All H atoms were positioned geometrically and constrained to refine with the parents atoms using the riding-model approximation, with C—H = 0.93 - 0.97Å and Uiso(H) = 1.2 Ueq(C). The crystal used was an inversion twin with refined twin components ratio of 0.60 (1)/0.40 (1).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
[Cu2(C18H14Cl4N2O2)2] | Z = 4 |
Mr = 990.30 | F(000) = 1988 |
Orthorhombic, Pca21 | Dx = 1.697 Mg m−3 |
Hall symbol: P 2c -2ac | Mo Kα radiation, λ = 0.71073 Å |
a = 26.6927 (16) Å | µ = 1.70 mm−1 |
b = 7.7775 (4) Å | T = 291 K |
c = 18.6689 (9) Å | Needle, dark-red |
V = 3875.7 (4) Å3 | 0.36 × 0.18 × 0.16 mm |
Bruker SMART APEXII CCD diffractometer | 8990 independent reflections |
Radiation source: fine-focus sealed tube | 6793 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
φ and ω scans | θmax = 27.9°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −35→34 |
Tmin = 0.581, Tmax = 0.773 | k = −10→10 |
18623 measured reflections | l = −24→23 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.085 | w = 1/[σ2(Fo2) + (0.0355P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max = 0.001 |
8990 reflections | Δρmax = 0.43 e Å−3 |
488 parameters | Δρmin = −0.35 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 4247 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Flack parameter: 0.605 (10) |
[Cu2(C18H14Cl4N2O2)2] | V = 3875.7 (4) Å3 |
Mr = 990.30 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 26.6927 (16) Å | µ = 1.70 mm−1 |
b = 7.7775 (4) Å | T = 291 K |
c = 18.6689 (9) Å | 0.36 × 0.18 × 0.16 mm |
Bruker SMART APEXII CCD diffractometer | 8990 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 6793 reflections with I > 2σ(I) |
Tmin = 0.581, Tmax = 0.773 | Rint = 0.034 |
18623 measured reflections | θmax = 27.9° |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.085 | Δρmax = 0.43 e Å−3 |
S = 0.99 | Δρmin = −0.35 e Å−3 |
8990 reflections | Absolute structure: Flack (1983), 4247 Friedel pairs |
488 parameters | Flack parameter: 0.605 (10) |
1 restraint |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | 0.337328 (15) | 0.58203 (6) | 0.49568 (2) | 0.03303 (11) | |
Cu2 | 0.372623 (16) | 1.16823 (6) | 0.50686 (2) | 0.03338 (11) | |
Cl1 | 0.16981 (4) | 0.56157 (19) | 0.41600 (6) | 0.0637 (4) | |
Cl2 | 0.10357 (4) | 0.81832 (18) | 0.66592 (6) | 0.0630 (3) | |
Cl3 | 0.62687 (5) | 0.9809 (2) | 0.39111 (8) | 0.0819 (5) | |
Cl4 | 0.44901 (4) | 1.14708 (19) | 0.27711 (5) | 0.0632 (4) | |
Cl5 | 0.30179 (5) | 1.27744 (18) | 0.73675 (6) | 0.0610 (3) | |
Cl6 | 0.11528 (5) | 1.28198 (19) | 0.62737 (8) | 0.0720 (4) | |
Cl7 | 0.57210 (5) | 0.5842 (2) | 0.30261 (8) | 0.0873 (5) | |
Cl8 | 0.50484 (4) | 0.49330 (18) | 0.57186 (6) | 0.0551 (3) | |
O1 | 0.26712 (9) | 0.5760 (4) | 0.48373 (13) | 0.0397 (7) | |
O2 | 0.41409 (10) | 1.1451 (4) | 0.42485 (13) | 0.0409 (7) | |
O3 | 0.33216 (9) | 1.2300 (4) | 0.58740 (14) | 0.0403 (7) | |
O4 | 0.40552 (9) | 0.5174 (3) | 0.50582 (15) | 0.0408 (6) | |
N1 | 0.33065 (11) | 0.6318 (4) | 0.60038 (16) | 0.0339 (8) | |
N2 | 0.42848 (12) | 1.1052 (4) | 0.57284 (16) | 0.0334 (7) | |
N3 | 0.31196 (12) | 1.1706 (4) | 0.44287 (17) | 0.0357 (8) | |
N4 | 0.34356 (12) | 0.6048 (4) | 0.38931 (17) | 0.0338 (8) | |
C1 | 0.23262 (14) | 0.6340 (5) | 0.5258 (2) | 0.0345 (9) | |
C2 | 0.18203 (13) | 0.6377 (5) | 0.5021 (2) | 0.0386 (8) | |
C3 | 0.14355 (15) | 0.6947 (6) | 0.5433 (2) | 0.0435 (10) | |
H3 | 0.1111 | 0.6963 | 0.5253 | 0.052* | |
C4 | 0.15322 (15) | 0.7505 (6) | 0.6124 (2) | 0.0411 (10) | |
C5 | 0.20089 (14) | 0.7489 (5) | 0.6389 (2) | 0.0389 (9) | |
H5 | 0.2070 | 0.7873 | 0.6853 | 0.047* | |
C6 | 0.24090 (14) | 0.6895 (5) | 0.5963 (2) | 0.0326 (8) | |
C7 | 0.28933 (14) | 0.6746 (5) | 0.6297 (2) | 0.0370 (9) | |
H7 | 0.2906 | 0.6990 | 0.6785 | 0.044* | |
C8 | 0.37456 (14) | 0.6148 (6) | 0.6481 (2) | 0.0368 (10) | |
H8A | 0.3928 | 0.5111 | 0.6357 | 0.044* | |
H8B | 0.3632 | 0.6036 | 0.6972 | 0.044* | |
C9 | 0.40930 (13) | 0.7679 (5) | 0.6423 (2) | 0.0364 (9) | |
H9A | 0.4388 | 0.7461 | 0.6713 | 0.044* | |
H9B | 0.4202 | 0.7788 | 0.5930 | 0.044* | |
C10 | 0.38622 (14) | 0.9362 (5) | 0.6657 (2) | 0.0368 (9) | |
H10A | 0.3795 | 0.9313 | 0.7167 | 0.044* | |
H10B | 0.3544 | 0.9511 | 0.6413 | 0.044* | |
C11 | 0.41906 (15) | 1.0905 (5) | 0.65037 (19) | 0.0371 (9) | |
H11A | 0.4027 | 1.1940 | 0.6675 | 0.045* | |
H11B | 0.4506 | 1.0785 | 0.6756 | 0.045* | |
C12 | 0.47348 (15) | 1.0699 (6) | 0.5522 (2) | 0.0369 (10) | |
H12 | 0.4964 | 1.0428 | 0.5880 | 0.044* | |
C13 | 0.49213 (14) | 1.0681 (5) | 0.47969 (19) | 0.0357 (9) | |
C14 | 0.54318 (16) | 1.0277 (6) | 0.4704 (2) | 0.0485 (12) | |
H14 | 0.5629 | 1.0001 | 0.5099 | 0.058* | |
C15 | 0.56376 (17) | 1.0291 (6) | 0.4032 (2) | 0.0527 (12) | |
C16 | 0.53470 (17) | 1.0663 (6) | 0.3442 (2) | 0.0484 (11) | |
H16 | 0.5490 | 1.0660 | 0.2988 | 0.058* | |
C17 | 0.48514 (15) | 1.1036 (6) | 0.3521 (2) | 0.0406 (10) | |
C18 | 0.46083 (16) | 1.1077 (5) | 0.4208 (2) | 0.0377 (10) | |
C19 | 0.28383 (14) | 1.2284 (5) | 0.5951 (2) | 0.0339 (9) | |
C20 | 0.26211 (15) | 1.2550 (6) | 0.6637 (2) | 0.0410 (10) | |
C21 | 0.21145 (17) | 1.2690 (6) | 0.6737 (2) | 0.0476 (11) | |
H21 | 0.1986 | 1.2889 | 0.7193 | 0.057* | |
C22 | 0.17914 (16) | 1.2535 (6) | 0.6154 (2) | 0.0472 (11) | |
C23 | 0.19810 (15) | 1.2208 (6) | 0.5491 (2) | 0.0445 (11) | |
H23 | 0.1764 | 1.2078 | 0.5105 | 0.053* | |
C24 | 0.24970 (15) | 1.2066 (5) | 0.5385 (2) | 0.0381 (10) | |
C25 | 0.26634 (15) | 1.1856 (5) | 0.4653 (2) | 0.0378 (10) | |
H25 | 0.2415 | 1.1826 | 0.4304 | 0.045* | |
C26 | 0.31740 (15) | 1.1496 (5) | 0.36388 (19) | 0.0365 (9) | |
H26A | 0.3446 | 1.2217 | 0.3471 | 0.044* | |
H26B | 0.2869 | 1.1879 | 0.3406 | 0.044* | |
C27 | 0.32770 (15) | 0.9657 (5) | 0.3430 (2) | 0.0374 (10) | |
H27A | 0.3576 | 0.9276 | 0.3679 | 0.045* | |
H27B | 0.3348 | 0.9623 | 0.2920 | 0.045* | |
C28 | 0.28539 (14) | 0.8383 (5) | 0.3588 (2) | 0.0396 (10) | |
H28A | 0.2754 | 0.8507 | 0.4085 | 0.048* | |
H28B | 0.2567 | 0.8669 | 0.3293 | 0.048* | |
C29 | 0.29957 (15) | 0.6540 (5) | 0.3455 (2) | 0.0371 (10) | |
H29 | 0.2830 | 0.5809 | 0.3140 | 0.045* | |
C30 | 0.38488 (16) | 0.5911 (6) | 0.3557 (2) | 0.0408 (10) | |
H30 | 0.3831 | 0.5974 | 0.3060 | 0.049* | |
C31 | 0.43377 (14) | 0.5672 (6) | 0.3857 (2) | 0.0397 (10) | |
C32 | 0.47492 (17) | 0.5804 (6) | 0.3381 (2) | 0.0497 (11) | |
H32 | 0.4693 | 0.5975 | 0.2895 | 0.060* | |
C33 | 0.52243 (17) | 0.5682 (6) | 0.3633 (3) | 0.0536 (12) | |
C34 | 0.53194 (16) | 0.5446 (6) | 0.4350 (2) | 0.0489 (11) | |
H34 | 0.5648 | 0.5399 | 0.4516 | 0.059* | |
C35 | 0.49241 (14) | 0.5279 (5) | 0.4820 (2) | 0.0403 (10) | |
C36 | 0.44190 (14) | 0.5369 (5) | 0.4595 (2) | 0.0365 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0270 (2) | 0.0393 (2) | 0.0328 (2) | 0.0001 (2) | 0.0010 (2) | 0.0004 (2) |
Cu2 | 0.0324 (2) | 0.0408 (3) | 0.0269 (2) | 0.0028 (2) | −0.0005 (2) | −0.0008 (2) |
Cl1 | 0.0383 (6) | 0.1084 (11) | 0.0443 (6) | −0.0003 (7) | −0.0076 (5) | −0.0216 (7) |
Cl2 | 0.0434 (6) | 0.0912 (10) | 0.0544 (7) | 0.0174 (6) | 0.0098 (5) | −0.0116 (7) |
Cl3 | 0.0438 (7) | 0.1340 (15) | 0.0678 (8) | 0.0229 (8) | 0.0065 (6) | −0.0041 (9) |
Cl4 | 0.0514 (7) | 0.1088 (11) | 0.0296 (5) | −0.0003 (7) | −0.0031 (5) | −0.0046 (6) |
Cl5 | 0.0560 (7) | 0.0944 (10) | 0.0324 (5) | −0.0004 (7) | 0.0039 (5) | −0.0003 (6) |
Cl6 | 0.0393 (6) | 0.0929 (10) | 0.0837 (9) | 0.0038 (7) | 0.0194 (6) | 0.0158 (8) |
Cl7 | 0.0457 (7) | 0.1407 (15) | 0.0755 (9) | 0.0138 (8) | 0.0286 (7) | 0.0277 (9) |
Cl8 | 0.0365 (6) | 0.0757 (9) | 0.0529 (6) | 0.0033 (6) | −0.0062 (5) | 0.0012 (6) |
O1 | 0.0267 (13) | 0.0592 (18) | 0.0333 (14) | −0.0012 (13) | 0.0027 (11) | −0.0040 (13) |
O2 | 0.0325 (15) | 0.061 (2) | 0.0297 (14) | 0.0029 (14) | −0.0006 (11) | −0.0028 (13) |
O3 | 0.0297 (15) | 0.0592 (19) | 0.0321 (14) | 0.0018 (13) | 0.0018 (12) | −0.0064 (14) |
O4 | 0.0253 (13) | 0.0590 (16) | 0.0382 (14) | 0.0055 (12) | 0.0033 (13) | 0.0037 (16) |
N1 | 0.0323 (18) | 0.036 (2) | 0.0333 (17) | −0.0036 (15) | −0.0036 (14) | 0.0023 (15) |
N2 | 0.0380 (19) | 0.037 (2) | 0.0248 (15) | −0.0019 (16) | −0.0042 (14) | 0.0008 (14) |
N3 | 0.0372 (19) | 0.039 (2) | 0.0306 (16) | 0.0060 (16) | −0.0023 (15) | −0.0020 (15) |
N4 | 0.0338 (18) | 0.0336 (19) | 0.0340 (17) | 0.0033 (16) | −0.0009 (14) | −0.0018 (15) |
C1 | 0.032 (2) | 0.034 (2) | 0.038 (2) | −0.0024 (17) | 0.0021 (16) | 0.0034 (17) |
C2 | 0.0291 (17) | 0.052 (2) | 0.0345 (19) | −0.0034 (16) | −0.0023 (19) | −0.003 (2) |
C3 | 0.029 (2) | 0.057 (3) | 0.045 (2) | 0.000 (2) | −0.0037 (18) | 0.000 (2) |
C4 | 0.035 (2) | 0.051 (3) | 0.037 (2) | 0.003 (2) | 0.0070 (18) | −0.002 (2) |
C5 | 0.037 (2) | 0.048 (2) | 0.0319 (19) | 0.003 (2) | 0.0021 (18) | −0.0021 (19) |
C6 | 0.0289 (19) | 0.035 (2) | 0.0341 (19) | −0.0013 (17) | 0.0013 (16) | 0.0026 (18) |
C7 | 0.035 (2) | 0.048 (3) | 0.0278 (19) | −0.003 (2) | 0.0014 (17) | 0.0032 (19) |
C8 | 0.032 (2) | 0.045 (3) | 0.033 (2) | 0.0002 (19) | −0.0099 (17) | 0.0078 (19) |
C9 | 0.0267 (19) | 0.044 (2) | 0.038 (2) | 0.0003 (19) | −0.0029 (16) | 0.0020 (19) |
C10 | 0.035 (2) | 0.048 (2) | 0.0269 (18) | −0.0002 (19) | −0.0026 (16) | 0.0021 (18) |
C11 | 0.036 (2) | 0.048 (3) | 0.0275 (19) | −0.004 (2) | −0.0003 (16) | −0.0010 (18) |
C12 | 0.032 (2) | 0.048 (3) | 0.0303 (19) | −0.0076 (19) | −0.0091 (17) | 0.0041 (19) |
C13 | 0.035 (2) | 0.036 (2) | 0.036 (2) | −0.0020 (18) | 0.0018 (16) | 0.0000 (18) |
C14 | 0.037 (2) | 0.064 (3) | 0.045 (2) | 0.004 (2) | 0.0009 (19) | −0.003 (2) |
C15 | 0.039 (2) | 0.070 (3) | 0.049 (3) | 0.010 (2) | 0.004 (2) | −0.006 (2) |
C16 | 0.043 (3) | 0.065 (3) | 0.036 (2) | −0.002 (2) | 0.0077 (19) | −0.006 (2) |
C17 | 0.040 (2) | 0.053 (3) | 0.0287 (19) | −0.003 (2) | −0.0015 (17) | −0.0042 (19) |
C18 | 0.041 (2) | 0.039 (3) | 0.033 (2) | −0.005 (2) | −0.0012 (18) | −0.0049 (18) |
C19 | 0.037 (2) | 0.030 (2) | 0.035 (2) | 0.0015 (18) | −0.0003 (17) | 0.0061 (17) |
C20 | 0.040 (2) | 0.049 (3) | 0.035 (2) | 0.001 (2) | 0.0070 (18) | 0.003 (2) |
C21 | 0.049 (3) | 0.052 (3) | 0.041 (2) | 0.000 (2) | 0.014 (2) | 0.006 (2) |
C22 | 0.035 (2) | 0.048 (3) | 0.059 (3) | −0.001 (2) | 0.016 (2) | 0.014 (2) |
C23 | 0.036 (2) | 0.050 (3) | 0.047 (2) | −0.002 (2) | −0.001 (2) | 0.004 (2) |
C24 | 0.036 (2) | 0.036 (2) | 0.042 (2) | 0.0010 (19) | 0.0015 (19) | 0.0034 (19) |
C25 | 0.034 (2) | 0.041 (3) | 0.039 (2) | 0.002 (2) | −0.0116 (17) | −0.0007 (18) |
C26 | 0.035 (2) | 0.048 (3) | 0.0264 (19) | 0.002 (2) | −0.0018 (16) | −0.0009 (18) |
C27 | 0.038 (2) | 0.042 (3) | 0.032 (2) | −0.0019 (19) | 0.0000 (16) | −0.0052 (18) |
C28 | 0.034 (2) | 0.046 (3) | 0.039 (2) | −0.001 (2) | −0.0068 (17) | −0.002 (2) |
C29 | 0.037 (2) | 0.043 (2) | 0.0307 (19) | −0.001 (2) | −0.0120 (17) | −0.0063 (19) |
C30 | 0.040 (2) | 0.048 (3) | 0.034 (2) | 0.002 (2) | 0.0044 (18) | −0.001 (2) |
C31 | 0.031 (2) | 0.042 (2) | 0.046 (2) | 0.0037 (19) | 0.0032 (18) | 0.003 (2) |
C32 | 0.043 (3) | 0.062 (3) | 0.044 (3) | 0.008 (2) | 0.006 (2) | 0.008 (2) |
C33 | 0.038 (2) | 0.064 (3) | 0.058 (3) | 0.005 (2) | 0.018 (2) | 0.012 (3) |
C34 | 0.032 (2) | 0.054 (3) | 0.060 (3) | −0.003 (2) | 0.010 (2) | 0.008 (2) |
C35 | 0.032 (2) | 0.040 (2) | 0.049 (2) | 0.0047 (18) | 0.0009 (18) | 0.007 (2) |
C36 | 0.028 (2) | 0.036 (2) | 0.046 (2) | 0.0055 (18) | 0.0040 (17) | −0.0001 (18) |
Cu1—O1 | 1.888 (2) | C10—C11 | 1.513 (5) |
Cu1—O4 | 1.898 (2) | C10—H10A | 0.9700 |
Cu1—N4 | 2.000 (3) | C10—H10B | 0.9700 |
Cu1—N1 | 2.001 (3) | C11—H11A | 0.9700 |
Cu2—O2 | 1.898 (3) | C11—H11B | 0.9700 |
Cu2—O3 | 1.913 (3) | C12—C13 | 1.443 (5) |
Cu2—N2 | 1.995 (3) | C12—H12 | 0.9300 |
Cu2—N3 | 2.012 (3) | C13—C14 | 1.409 (5) |
Cu2—O4i | 2.854 (3) | C13—C18 | 1.415 (5) |
Cl1—C2 | 1.744 (4) | C14—C15 | 1.369 (6) |
Cl2—C4 | 1.741 (4) | C14—H14 | 0.9300 |
Cl3—C15 | 1.740 (4) | C15—C16 | 1.378 (6) |
Cl4—C17 | 1.733 (4) | C16—C17 | 1.362 (6) |
Cl5—C20 | 1.735 (4) | C16—H16 | 0.9300 |
Cl6—C22 | 1.733 (4) | C17—C18 | 1.437 (5) |
Cl7—C33 | 1.748 (4) | C19—C24 | 1.405 (5) |
Cl8—C35 | 1.730 (4) | C19—C20 | 1.422 (5) |
O1—C1 | 1.292 (4) | C20—C21 | 1.369 (6) |
O2—C18 | 1.283 (5) | C21—C22 | 1.395 (6) |
O3—C19 | 1.298 (4) | C21—H21 | 0.9300 |
O4—C36 | 1.309 (4) | C22—C23 | 1.360 (6) |
N1—C7 | 1.276 (5) | C23—C24 | 1.396 (5) |
N1—C8 | 1.478 (5) | C23—H23 | 0.9300 |
N2—C12 | 1.291 (5) | C24—C25 | 1.447 (5) |
N2—C11 | 1.473 (5) | C25—H25 | 0.9300 |
N3—C25 | 1.293 (5) | C26—C27 | 1.507 (5) |
N3—C26 | 1.491 (5) | C26—H26A | 0.9700 |
N4—C30 | 1.273 (5) | C26—H26B | 0.9700 |
N4—C29 | 1.482 (5) | C27—C28 | 1.532 (5) |
C1—C6 | 1.403 (5) | C27—H27A | 0.9700 |
C1—C2 | 1.421 (5) | C27—H27B | 0.9700 |
C2—C3 | 1.358 (5) | C28—C29 | 1.503 (6) |
C3—C4 | 1.385 (5) | C28—H28A | 0.9700 |
C3—H3 | 0.9300 | C28—H28B | 0.9700 |
C4—C5 | 1.365 (5) | C29—H29 | 0.9300 |
C5—C6 | 1.409 (5) | C30—C31 | 1.432 (6) |
C5—H5 | 0.9300 | C30—H30 | 0.9300 |
C6—C7 | 1.440 (5) | C31—C36 | 1.415 (6) |
C7—H7 | 0.9300 | C31—C32 | 1.417 (6) |
C8—C9 | 1.513 (5) | C32—C33 | 1.356 (6) |
C8—H8A | 0.9700 | C32—H32 | 0.9300 |
C8—H8B | 0.9700 | C33—C34 | 1.375 (6) |
C9—C10 | 1.512 (5) | C34—C35 | 1.379 (5) |
C9—H9A | 0.9700 | C34—H34 | 0.9300 |
C9—H9B | 0.9700 | C35—C36 | 1.414 (5) |
O1—Cu1—O4 | 163.19 (11) | C14—C13—C12 | 116.8 (3) |
O1—Cu1—N4 | 88.14 (12) | C18—C13—C12 | 121.6 (4) |
O4—Cu1—N4 | 92.45 (12) | C15—C14—C13 | 119.9 (4) |
O1—Cu1—N1 | 91.82 (11) | C15—C14—H14 | 120.0 |
O4—Cu1—N1 | 92.25 (12) | C13—C14—H14 | 120.0 |
N4—Cu1—N1 | 163.77 (13) | C14—C15—C16 | 120.5 (4) |
O2—Cu2—O3 | 170.89 (13) | C14—C15—Cl3 | 120.4 (3) |
O2—Cu2—N2 | 92.23 (12) | C16—C15—Cl3 | 119.1 (3) |
O3—Cu2—N2 | 89.91 (12) | C17—C16—C15 | 120.4 (4) |
O2—Cu2—N3 | 89.50 (12) | C17—C16—H16 | 119.8 |
O3—Cu2—N3 | 90.57 (12) | C15—C16—H16 | 119.8 |
N2—Cu2—N3 | 165.95 (14) | C16—C17—C18 | 122.6 (4) |
O2—Cu2—O4i | 84.56 (10) | C16—C17—Cl4 | 119.7 (3) |
O3—Cu2—O4i | 86.56 (10) | C18—C17—Cl4 | 117.7 (3) |
N2—Cu2—O4i | 90.47 (11) | O2—C18—C13 | 125.3 (4) |
N3—Cu2—O4i | 103.57 (11) | O2—C18—C17 | 119.8 (4) |
C1—O1—Cu1 | 128.9 (2) | C13—C18—C17 | 115.0 (4) |
C18—O2—Cu2 | 129.5 (2) | O3—C19—C24 | 124.2 (4) |
C19—O3—Cu2 | 130.2 (2) | O3—C19—C20 | 120.2 (4) |
C36—O4—Cu1 | 128.0 (3) | C24—C19—C20 | 115.5 (4) |
C7—N1—C8 | 116.8 (3) | C21—C20—C19 | 122.5 (4) |
C7—N1—Cu1 | 123.2 (3) | C21—C20—Cl5 | 119.2 (3) |
C8—N1—Cu1 | 120.0 (3) | C19—C20—Cl5 | 118.3 (3) |
C12—N2—C11 | 115.8 (3) | C20—C21—C22 | 119.8 (4) |
C12—N2—Cu2 | 124.3 (3) | C20—C21—H21 | 120.1 |
C11—N2—Cu2 | 119.9 (2) | C22—C21—H21 | 120.1 |
C25—N3—C26 | 115.0 (3) | C23—C22—C21 | 119.8 (4) |
C25—N3—Cu2 | 124.5 (3) | C23—C22—Cl6 | 120.5 (4) |
C26—N3—Cu2 | 120.5 (2) | C21—C22—Cl6 | 119.7 (3) |
C30—N4—C29 | 115.8 (3) | C22—C23—C24 | 120.7 (4) |
C30—N4—Cu1 | 123.6 (3) | C22—C23—H23 | 119.6 |
C29—N4—Cu1 | 120.3 (2) | C24—C23—H23 | 119.6 |
O1—C1—C6 | 124.5 (3) | C23—C24—C19 | 121.6 (4) |
O1—C1—C2 | 119.7 (3) | C23—C24—C25 | 116.5 (4) |
C6—C1—C2 | 115.8 (3) | C19—C24—C25 | 121.6 (4) |
C3—C2—C1 | 123.3 (4) | N3—C25—C24 | 127.3 (4) |
C3—C2—Cl1 | 119.5 (3) | N3—C25—H25 | 116.4 |
C1—C2—Cl1 | 117.2 (3) | C24—C25—H25 | 116.4 |
C2—C3—C4 | 119.3 (4) | N3—C26—C27 | 112.2 (3) |
C2—C3—H3 | 120.4 | N3—C26—H26A | 109.2 |
C4—C3—H3 | 120.4 | C27—C26—H26A | 109.2 |
C5—C4—C3 | 120.5 (4) | N3—C26—H26B | 109.2 |
C5—C4—Cl2 | 120.3 (3) | C27—C26—H26B | 109.2 |
C3—C4—Cl2 | 119.2 (3) | H26A—C26—H26B | 107.9 |
C4—C5—C6 | 120.3 (4) | C26—C27—C28 | 115.4 (3) |
C4—C5—H5 | 119.8 | C26—C27—H27A | 108.4 |
C6—C5—H5 | 119.8 | C28—C27—H27A | 108.4 |
C1—C6—C5 | 120.7 (4) | C26—C27—H27B | 108.4 |
C1—C6—C7 | 121.6 (3) | C28—C27—H27B | 108.4 |
C5—C6—C7 | 117.5 (4) | H27A—C27—H27B | 107.5 |
N1—C7—C6 | 127.6 (4) | C29—C28—C27 | 113.5 (3) |
N1—C7—H7 | 116.2 | C29—C28—H28A | 108.9 |
C6—C7—H7 | 116.2 | C27—C28—H28A | 108.9 |
N1—C8—C9 | 111.9 (3) | C29—C28—H28B | 108.9 |
N1—C8—H8A | 109.2 | C27—C28—H28B | 108.9 |
C9—C8—H8A | 109.2 | H28A—C28—H28B | 107.7 |
N1—C8—H8B | 109.2 | N4—C29—C28 | 110.7 (3) |
C9—C8—H8B | 109.2 | N4—C29—H29 | 124.6 |
H8A—C8—H8B | 107.9 | C28—C29—H29 | 124.6 |
C10—C9—C8 | 114.3 (3) | N4—C30—C31 | 127.4 (4) |
C10—C9—H9A | 108.7 | N4—C30—H30 | 116.3 |
C8—C9—H9A | 108.7 | C31—C30—H30 | 116.3 |
C10—C9—H9B | 108.7 | C36—C31—C32 | 120.3 (4) |
C8—C9—H9B | 108.7 | C36—C31—C30 | 122.9 (4) |
H9A—C9—H9B | 107.6 | C32—C31—C30 | 116.9 (4) |
C9—C10—C11 | 113.3 (3) | C33—C32—C31 | 120.2 (4) |
C9—C10—H10A | 108.9 | C33—C32—H32 | 119.9 |
C11—C10—H10A | 108.9 | C31—C32—H32 | 119.9 |
C9—C10—H10B | 108.9 | C32—C33—C34 | 121.3 (4) |
C11—C10—H10B | 108.9 | C32—C33—Cl7 | 118.7 (4) |
H10A—C10—H10B | 107.7 | C34—C33—Cl7 | 120.0 (4) |
N2—C11—C10 | 110.3 (3) | C33—C34—C35 | 119.4 (4) |
N2—C11—H11A | 109.6 | C33—C34—H34 | 120.3 |
C10—C11—H11A | 109.6 | C35—C34—H34 | 120.3 |
N2—C11—H11B | 109.6 | C34—C35—C36 | 122.4 (4) |
C10—C11—H11B | 109.6 | C34—C35—Cl8 | 119.0 (3) |
H11A—C11—H11B | 108.1 | C36—C35—Cl8 | 118.6 (3) |
N2—C12—C13 | 127.1 (4) | O4—C36—C35 | 120.4 (4) |
N2—C12—H12 | 116.4 | O4—C36—C31 | 123.3 (4) |
C13—C12—H12 | 116.4 | C35—C36—C31 | 116.4 (3) |
C14—C13—C18 | 121.6 (4) | ||
O4—Cu1—O1—C1 | 120.7 (4) | N2—C12—C13—C14 | 179.2 (4) |
N4—Cu1—O1—C1 | −146.9 (3) | N2—C12—C13—C18 | 0.2 (7) |
N1—Cu1—O1—C1 | 16.8 (3) | C18—C13—C14—C15 | 1.2 (7) |
N2—Cu2—O2—C18 | −2.0 (4) | C12—C13—C14—C15 | −177.9 (4) |
N3—Cu2—O2—C18 | −168.1 (4) | C13—C14—C15—C16 | −1.3 (8) |
N2—Cu2—O3—C19 | −151.8 (3) | C13—C14—C15—Cl3 | 179.5 (3) |
N3—Cu2—O3—C19 | 14.2 (3) | C14—C15—C16—C17 | 0.5 (8) |
O1—Cu1—O4—C36 | 108.6 (5) | Cl3—C15—C16—C17 | 179.7 (4) |
N4—Cu1—O4—C36 | 16.9 (3) | C15—C16—C17—C18 | 0.5 (7) |
N1—Cu1—O4—C36 | −147.6 (3) | C15—C16—C17—Cl4 | −179.1 (4) |
O1—Cu1—N1—C7 | −12.0 (3) | Cu2—O2—C18—C13 | 2.5 (6) |
O4—Cu1—N1—C7 | −175.7 (3) | Cu2—O2—C18—C17 | −177.6 (3) |
N4—Cu1—N1—C7 | 77.6 (6) | C14—C13—C18—O2 | 179.7 (4) |
O1—Cu1—N1—C8 | 166.3 (3) | C12—C13—C18—O2 | −1.3 (7) |
O4—Cu1—N1—C8 | 2.6 (3) | C14—C13—C18—C17 | −0.1 (6) |
N4—Cu1—N1—C8 | −104.2 (5) | C12—C13—C18—C17 | 178.8 (4) |
O2—Cu2—N2—C12 | 0.9 (3) | C16—C17—C18—O2 | 179.4 (4) |
O3—Cu2—N2—C12 | −170.2 (4) | Cl4—C17—C18—O2 | −1.0 (6) |
N3—Cu2—N2—C12 | 97.8 (6) | C16—C17—C18—C13 | −0.7 (6) |
O2—Cu2—N2—C11 | −176.9 (3) | Cl4—C17—C18—C13 | 178.9 (3) |
O3—Cu2—N2—C11 | 12.0 (3) | Cu2—O3—C19—C24 | −11.7 (6) |
N3—Cu2—N2—C11 | −80.0 (6) | Cu2—O3—C19—C20 | 170.4 (3) |
O2—Cu2—N3—C25 | −179.5 (3) | O3—C19—C20—C21 | 174.3 (4) |
O3—Cu2—N3—C25 | −8.6 (3) | C24—C19—C20—C21 | −3.8 (6) |
N2—Cu2—N3—C25 | 83.3 (7) | O3—C19—C20—Cl5 | −3.5 (5) |
O2—Cu2—N3—C26 | 2.2 (3) | C24—C19—C20—Cl5 | 178.4 (3) |
O3—Cu2—N3—C26 | 173.1 (3) | C19—C20—C21—C22 | 1.3 (7) |
N2—Cu2—N3—C26 | −95.0 (6) | Cl5—C20—C21—C22 | 179.2 (3) |
O1—Cu1—N4—C30 | −169.2 (4) | C20—C21—C22—C23 | 1.4 (7) |
O4—Cu1—N4—C30 | −6.0 (4) | C20—C21—C22—Cl6 | −176.8 (3) |
N1—Cu1—N4—C30 | 100.7 (5) | C21—C22—C23—C24 | −1.5 (7) |
O1—Cu1—N4—C29 | 16.0 (3) | Cl6—C22—C23—C24 | 176.7 (3) |
O4—Cu1—N4—C29 | 179.2 (3) | C22—C23—C24—C19 | −1.2 (6) |
N1—Cu1—N4—C29 | −74.2 (6) | C22—C23—C24—C25 | −175.2 (4) |
O4i—Cu2—O2—C18 | 88.2 (4) | O3—C19—C24—C23 | −174.4 (4) |
O4i—Cu2—O3—C19 | 117.7 (3) | C20—C19—C24—C23 | 3.7 (6) |
O4i—Cu2—N2—C12 | −83.7 (3) | O3—C19—C24—C25 | −0.7 (7) |
O4i—Cu2—N2—C11 | 98.5 (3) | C20—C19—C24—C25 | 177.3 (4) |
O4i—Cu2—N3—C25 | −95.2 (3) | C26—N3—C25—C24 | 179.6 (4) |
O4i—Cu2—N3—C26 | 86.5 (3) | Cu2—N3—C25—C24 | 1.3 (7) |
Cu1—O1—C1—C6 | −11.3 (5) | C23—C24—C25—N3 | 179.7 (4) |
Cu1—O1—C1—C2 | 171.3 (3) | C19—C24—C25—N3 | 5.7 (8) |
O1—C1—C2—C3 | 179.2 (4) | C25—N3—C26—C27 | −102.5 (4) |
C6—C1—C2—C3 | 1.6 (6) | Cu2—N3—C26—C27 | 75.9 (4) |
O1—C1—C2—Cl1 | 0.1 (5) | N3—C26—C27—C28 | 64.9 (4) |
C6—C1—C2—Cl1 | −177.5 (3) | C26—C27—C28—C29 | −173.0 (3) |
C1—C2—C3—C4 | −0.9 (7) | C30—N4—C29—C28 | −105.5 (4) |
Cl1—C2—C3—C4 | 178.2 (3) | Cu1—N4—C29—C28 | 69.7 (4) |
C2—C3—C4—C5 | 0.3 (7) | C27—C28—C29—N4 | 58.2 (4) |
C2—C3—C4—Cl2 | −178.3 (3) | C29—N4—C30—C31 | 171.4 (4) |
C3—C4—C5—C6 | −0.4 (6) | Cu1—N4—C30—C31 | −3.6 (7) |
Cl2—C4—C5—C6 | 178.2 (3) | N4—C30—C31—C36 | 7.0 (7) |
O1—C1—C6—C5 | −179.2 (4) | N4—C30—C31—C32 | −171.1 (4) |
C2—C1—C6—C5 | −1.7 (5) | C36—C31—C32—C33 | −1.6 (7) |
O1—C1—C6—C7 | −4.4 (6) | C30—C31—C32—C33 | 176.5 (4) |
C2—C1—C6—C7 | 173.0 (3) | C31—C32—C33—C34 | −0.6 (7) |
C4—C5—C6—C1 | 1.2 (6) | C31—C32—C33—Cl7 | 179.7 (4) |
C4—C5—C6—C7 | −173.8 (4) | C32—C33—C34—C35 | 1.9 (7) |
C8—N1—C7—C6 | −175.9 (4) | Cl7—C33—C34—C35 | −178.4 (4) |
Cu1—N1—C7—C6 | 2.4 (6) | C33—C34—C35—C36 | −1.0 (7) |
C1—C6—C7—N1 | 8.7 (7) | C33—C34—C35—Cl8 | 178.5 (4) |
C5—C6—C7—N1 | −176.4 (4) | Cu1—O4—C36—C35 | 161.8 (3) |
C7—N1—C8—C9 | −103.0 (4) | Cu1—O4—C36—C31 | −18.3 (6) |
Cu1—N1—C8—C9 | 78.6 (4) | C34—C35—C36—O4 | 178.8 (4) |
N1—C8—C9—C10 | 63.3 (4) | Cl8—C35—C36—O4 | −0.7 (5) |
C8—C9—C10—C11 | −172.3 (3) | C34—C35—C36—C31 | −1.1 (6) |
C12—N2—C11—C10 | −109.1 (4) | Cl8—C35—C36—C31 | 179.3 (3) |
Cu2—N2—C11—C10 | 68.9 (4) | C32—C31—C36—O4 | −177.5 (4) |
C9—C10—C11—N2 | 60.6 (4) | C30—C31—C36—O4 | 4.4 (7) |
C11—N2—C12—C13 | 177.6 (4) | C32—C31—C36—C35 | 2.4 (6) |
Cu2—N2—C12—C13 | −0.3 (6) | C30—C31—C36—C35 | −175.6 (4) |
Symmetry code: (i) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10B···O3 | 0.97 | 2.46 | 3.073 (5) | 121 |
C27—H27A···O2 | 0.97 | 2.50 | 3.098 (5) | 120 |
C28—H28A···O1 | 0.97 | 2.57 | 3.137 (5) | 118 |
HK and AAA thank PNU for support of this work. RK thanks the Science and Research Branch, Islamic Azad University.
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The design and construction of metal-organic coordination polymers (MOCPs) have attracted considerable attention, not only for their novel topologies but also for their potential in the area of magnetic applications and functional materials (Kido & Okamoto, 2002; Li et al., 2006). One of the key strategies in the construction of metal-organic coordination polymers is to select suitable bi- or multi-dentate bridging ligands. Among these, bis-bidentate NN- or NO-donor Schiff base ligands with aliphatic and aromatic spacers (Hannon et al., 1999; Lavalette et al., 2003) have attracted much attention because of the flexibility in their coordination modes and the resulting intermolecular interactions. The long chain aliphatic spacers or rigid aromatic spacers with large bite angles in these ligands favour the bis-bidentate coordination mode and allow the ligands to accomodate metal centers in one unit of the ligand. On the other hand, Schiff bases are one of the most prevalent ligands in coordination chemistry and their complexes are some of the most important stereochemical models in transition metal-organic chemistry, with their ease of preparation and structural variations (Granovski et al., 1993; Elmali et al., 2000).
The asymmetric unit of the title complex is shown in Fig. 1. The bond lengths and angles are comparable to those in related structures (Kargar & Kia, 2011a,b). The long apical Cu—O bond is shorter than the sum of the van der Waals (vdW) radii of these atoms [Cu, 1.43Å and O, 1.52 Å; Bondi, 1964] and is formed by a symmetry related O atom creating a one-dimenional polymer along [010] (Fig. 2). In the crystal there are intermolecular Cl4···Cl6(1/2 - x, y, -1/2 + z) [3.444 (2)Å] distances which are shorter than the sum of the van der Waals radii for Cl [3.50Å] atoms (Bondi, 1964; Fig. 3). In addition, intermolecular π–π interactions [Cg1···Cg2i = 3.736 (2)Å, (i) x, -1+y, z; Cg3···Cg4ii = 3.875 (3) Å, (ii) x, 1+y, z; Cg1,Cg2, Cg3 and Cg4 are the centroids of the (C1–C6), (C6–C8), (C13–C18) and (C31–C36) rings respectively].