Acta Cryst. (2009). E65, m1246 [ doi:10.1107/S1600536809038045 ]
In the title complex, [Cu(C12H15Cl2N2O)2], the CuII ion is coordinated by one N,O-bidentate and one N,N',O-tridentate Schiff base ligand, resulting in a distorted CuN3O2 square-based pyramidal coordination for the metal ion, with the O atoms lying trans to each other in the basal plane.
A mixture of 3,5-dichloro-2-hydroxybenzaldehyde (380 mg, 2 mmol), N,N-dimethylpropane-1,3-diamine (204 mg, 2 mmol) and CuCl2.4H2O (1 mmol, 169 mg) was stirred in methanol (10 ml) for 1 h. After keeping the filtrate in air for 8 d, green block-shaped crystals of (I) were formed.
All H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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).
| [Cu(C12H15Cl2N2O)2] | Z = 2 |
| Mr = 611.86 | F(000) = 630 |
| Triclinic, P1 | Dx = 1.510 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 9.4099 (17) Å | Cell parameters from 25 reflections |
| b = 12.548 (2) Å | θ = 9–12° |
| c = 12.603 (2) Å | µ = 1.24 mm−1 |
| α = 103.271 (7)° | T = 296 K |
| β = 110.907 (7)° | Block, green |
| γ = 90.614 (8)° | 0.28 × 0.24 × 0.15 mm |
| V = 1346.0 (4) Å3 |
| Enraf–Nonius CAD-4 diffractometer | 3718 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.022 |
| graphite | θmax = 26.0°, θmin = 1.7° |
| ω/2θ scans | h = −11→9 |
| Absorption correction: ψ scan (North et al., 1968) | k = −15→15 |
| Tmin = 0.723, Tmax = 0.836 | l = −15→15 |
| 7433 measured reflections | 200 standard reflections every 3 reflections |
| 5221 independent reflections | intensity decay: 1% |
| 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.112 | H-atom parameters constrained |
| S = 1.02 | w = 1/[σ2(Fo2) + (0.0569P)2 + 0.2468P] where P = (Fo2 + 2Fc2)/3 |
| 5221 reflections | (Δ/σ)max < 0.001 |
| 320 parameters | Δρmax = 0.39 e Å−3 |
| 0 restraints | Δρmin = −0.63 e Å−3 |
| [Cu(C12H15Cl2N2O)2] | γ = 90.614 (8)° |
| Mr = 611.86 | V = 1346.0 (4) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 9.4099 (17) Å | Mo Kα radiation |
| b = 12.548 (2) Å | µ = 1.24 mm−1 |
| c = 12.603 (2) Å | T = 296 K |
| α = 103.271 (7)° | 0.28 × 0.24 × 0.15 mm |
| β = 110.907 (7)° |
| Enraf–Nonius CAD-4 diffractometer | 3718 reflections with I > 2σ(I) |
| Absorption correction: ψ scan (North et al., 1968) | Rint = 0.022 |
| Tmin = 0.723, Tmax = 0.836 | θmax = 26.0° |
| 7433 measured reflections | 200 standard reflections every 3 reflections |
| 5221 independent reflections | intensity decay: 1% |
| R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
| wR(F2) = 0.112 | Δρmax = 0.39 e Å−3 |
| S = 1.02 | Δρmin = −0.63 e Å−3 |
| 5221 reflections | Absolute structure: ? |
| 320 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | ||
| C1 | 1.0980 (3) | 0.3757 (3) | 0.4415 (3) | 0.0422 (8) | |
| C2 | 0.9891 (3) | 0.2919 (3) | 0.4160 (3) | 0.0413 (7) | |
| H2 | 1.0083 | 0.2402 | 0.4606 | 0.050* | |
| C3 | 0.8480 (3) | 0.2824 (2) | 0.3233 (3) | 0.0370 (7) | |
| C4 | 0.8149 (3) | 0.3598 (2) | 0.2532 (3) | 0.0333 (6) | |
| C5 | 0.9332 (3) | 0.4456 (2) | 0.2853 (3) | 0.0368 (7) | |
| C6 | 1.0705 (3) | 0.4550 (3) | 0.3772 (3) | 0.0419 (8) | |
| H6 | 1.1440 | 0.5135 | 0.3961 | 0.050* | |
| C7 | 0.7331 (4) | 0.1966 (3) | 0.3072 (3) | 0.0412 (7) | |
| H7 | 0.7569 | 0.1558 | 0.3632 | 0.049* | |
| C8 | 0.4966 (4) | 0.0924 (3) | 0.2371 (3) | 0.0522 (9) | |
| H8A | 0.5532 | 0.0519 | 0.2930 | 0.063* | |
| H8B | 0.4442 | 0.0400 | 0.1623 | 0.063* | |
| C9 | 0.3798 (4) | 0.1536 (3) | 0.2794 (3) | 0.0659 (11) | |
| H9A | 0.3207 | 0.1011 | 0.2971 | 0.079* | |
| H9B | 0.4353 | 0.2075 | 0.3524 | 0.079* | |
| C10 | 0.2686 (4) | 0.2124 (3) | 0.1978 (3) | 0.0548 (9) | |
| H10A | 0.2111 | 0.1587 | 0.1251 | 0.066* | |
| H10B | 0.1966 | 0.2420 | 0.2332 | 0.066* | |
| C11 | 0.4186 (5) | 0.3915 (3) | 0.2752 (3) | 0.0642 (11) | |
| H11A | 0.4538 | 0.4524 | 0.2536 | 0.096* | |
| H11B | 0.5045 | 0.3644 | 0.3266 | 0.096* | |
| H11C | 0.3499 | 0.4154 | 0.3147 | 0.096* | |
| C12 | 0.2181 (4) | 0.3478 (3) | 0.0858 (4) | 0.0632 (11) | |
| H12A | 0.1488 | 0.3794 | 0.1217 | 0.095* | |
| H12B | 0.1634 | 0.2898 | 0.0177 | 0.095* | |
| H12C | 0.2630 | 0.4035 | 0.0630 | 0.095* | |
| C13 | 0.2720 (3) | 0.0918 (2) | −0.0966 (3) | 0.0333 (6) | |
| C14 | 0.1557 (3) | 0.0043 (2) | −0.1296 (3) | 0.0383 (7) | |
| C15 | 0.0300 (4) | −0.0163 (3) | −0.2318 (3) | 0.0428 (8) | |
| H15 | −0.0437 | −0.0744 | −0.2497 | 0.051* | |
| C16 | 0.0141 (3) | 0.0509 (3) | −0.3084 (3) | 0.0433 (8) | |
| C17 | 0.1206 (3) | 0.1374 (3) | −0.2816 (3) | 0.0404 (7) | |
| H17 | 0.1079 | 0.1819 | −0.3333 | 0.048* | |
| C18 | 0.2487 (3) | 0.1596 (2) | −0.1769 (3) | 0.0349 (7) | |
| C19 | 0.3603 (3) | 0.2499 (2) | −0.1558 (3) | 0.0354 (7) | |
| H19 | 0.3448 | 0.2842 | −0.2165 | 0.042* | |
| C20 | 0.5819 (3) | 0.3732 (2) | −0.0704 (3) | 0.0369 (7) | |
| H20A | 0.6133 | 0.4327 | 0.0004 | 0.044* | |
| H20B | 0.5278 | 0.4034 | −0.1363 | 0.044* | |
| C21 | 0.7230 (3) | 0.3241 (3) | −0.0862 (3) | 0.0425 (8) | |
| H21A | 0.7862 | 0.3808 | −0.0946 | 0.051* | |
| H21B | 0.7821 | 0.3016 | −0.0159 | 0.051* | |
| C22 | 0.6870 (4) | 0.2265 (3) | −0.1906 (3) | 0.0446 (8) | |
| H22A | 0.7819 | 0.2025 | −0.1970 | 0.054* | |
| H22B | 0.6344 | 0.1664 | −0.1782 | 0.054* | |
| C23 | 0.5059 (5) | 0.1530 (3) | −0.3886 (3) | 0.0611 (10) | |
| H23A | 0.4440 | 0.1730 | −0.4588 | 0.092* | |
| H23B | 0.4413 | 0.1185 | −0.3593 | 0.092* | |
| H23C | 0.5756 | 0.1028 | −0.4057 | 0.092* | |
| C24 | 0.6815 (5) | 0.3107 (3) | −0.3461 (3) | 0.0604 (10) | |
| H24A | 0.7537 | 0.2646 | −0.3658 | 0.091* | |
| H24B | 0.7353 | 0.3763 | −0.2877 | 0.091* | |
| H24C | 0.6145 | 0.3303 | −0.4150 | 0.091* | |
| Cl1 | 0.90023 (10) | 0.54424 (7) | 0.20416 (9) | 0.0563 (2) | |
| Cl2 | 1.27444 (10) | 0.38562 (9) | 0.55552 (8) | 0.0654 (3) | |
| Cl3 | 0.17577 (11) | −0.08122 (7) | −0.03566 (8) | 0.0597 (3) | |
| Cl4 | −0.14445 (10) | 0.02090 (9) | −0.43971 (8) | 0.0639 (3) | |
| Cu1 | 0.52922 (4) | 0.23541 (3) | 0.08518 (3) | 0.03432 (13) | |
| N1 | 0.6029 (3) | 0.1709 (2) | 0.2244 (2) | 0.0400 (6) | |
| N2 | 0.3386 (3) | 0.3034 (2) | 0.1693 (2) | 0.0460 (7) | |
| N3 | 0.4784 (3) | 0.28772 (18) | −0.0621 (2) | 0.0331 (6) | |
| N4 | 0.5920 (3) | 0.2517 (2) | −0.3004 (2) | 0.0414 (6) | |
| O1 | 0.6871 (2) | 0.35606 (17) | 0.16617 (18) | 0.0401 (5) | |
| O2 | 0.3892 (2) | 0.10554 (16) | −0.00087 (18) | 0.0400 (5) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0273 (16) | 0.054 (2) | 0.0371 (18) | 0.0020 (15) | 0.0087 (13) | 0.0013 (15) |
| C2 | 0.0361 (18) | 0.050 (2) | 0.0334 (17) | 0.0031 (15) | 0.0078 (14) | 0.0107 (15) |
| C3 | 0.0327 (16) | 0.0389 (17) | 0.0369 (17) | −0.0020 (13) | 0.0119 (14) | 0.0066 (14) |
| C4 | 0.0299 (16) | 0.0358 (16) | 0.0343 (16) | 0.0006 (13) | 0.0136 (13) | 0.0064 (13) |
| C5 | 0.0307 (16) | 0.0373 (17) | 0.0426 (18) | −0.0012 (13) | 0.0160 (14) | 0.0064 (14) |
| C6 | 0.0256 (16) | 0.0432 (18) | 0.051 (2) | −0.0064 (14) | 0.0155 (15) | −0.0016 (15) |
| C7 | 0.0425 (19) | 0.0410 (18) | 0.0408 (18) | 0.0001 (15) | 0.0109 (15) | 0.0191 (15) |
| C8 | 0.051 (2) | 0.050 (2) | 0.054 (2) | −0.0174 (17) | 0.0076 (17) | 0.0292 (17) |
| C9 | 0.064 (3) | 0.083 (3) | 0.057 (2) | −0.025 (2) | 0.025 (2) | 0.027 (2) |
| C10 | 0.048 (2) | 0.057 (2) | 0.068 (2) | −0.0110 (17) | 0.0346 (19) | 0.0102 (19) |
| C11 | 0.070 (3) | 0.056 (2) | 0.069 (3) | −0.011 (2) | 0.043 (2) | −0.007 (2) |
| C12 | 0.051 (2) | 0.065 (3) | 0.084 (3) | 0.014 (2) | 0.034 (2) | 0.024 (2) |
| C13 | 0.0286 (16) | 0.0334 (16) | 0.0360 (17) | 0.0000 (13) | 0.0120 (13) | 0.0053 (13) |
| C14 | 0.0353 (17) | 0.0332 (16) | 0.0457 (19) | −0.0014 (13) | 0.0150 (15) | 0.0089 (14) |
| C15 | 0.0328 (17) | 0.0397 (18) | 0.052 (2) | −0.0060 (14) | 0.0172 (15) | 0.0025 (15) |
| C16 | 0.0276 (16) | 0.054 (2) | 0.0412 (19) | 0.0013 (15) | 0.0101 (14) | 0.0022 (15) |
| C17 | 0.0324 (17) | 0.0500 (19) | 0.0388 (18) | 0.0007 (14) | 0.0128 (14) | 0.0121 (15) |
| C18 | 0.0293 (16) | 0.0393 (17) | 0.0369 (17) | 0.0005 (13) | 0.0132 (13) | 0.0093 (14) |
| C19 | 0.0325 (16) | 0.0386 (17) | 0.0381 (17) | 0.0011 (13) | 0.0145 (14) | 0.0132 (14) |
| C20 | 0.0403 (17) | 0.0333 (16) | 0.0357 (17) | −0.0091 (13) | 0.0118 (14) | 0.0103 (13) |
| C21 | 0.0342 (17) | 0.0462 (19) | 0.0477 (19) | −0.0060 (14) | 0.0139 (15) | 0.0153 (16) |
| C22 | 0.0420 (19) | 0.0457 (19) | 0.053 (2) | 0.0043 (15) | 0.0236 (16) | 0.0166 (16) |
| C23 | 0.069 (3) | 0.055 (2) | 0.057 (2) | −0.0106 (19) | 0.026 (2) | 0.0059 (19) |
| C24 | 0.071 (3) | 0.058 (2) | 0.063 (2) | −0.0083 (19) | 0.035 (2) | 0.0188 (19) |
| Cl1 | 0.0476 (5) | 0.0483 (5) | 0.0710 (6) | −0.0102 (4) | 0.0140 (4) | 0.0243 (4) |
| Cl2 | 0.0340 (5) | 0.0921 (8) | 0.0524 (6) | −0.0029 (5) | −0.0006 (4) | 0.0117 (5) |
| Cl3 | 0.0596 (6) | 0.0484 (5) | 0.0653 (6) | −0.0160 (4) | 0.0104 (5) | 0.0245 (5) |
| Cl4 | 0.0360 (5) | 0.0847 (7) | 0.0519 (6) | −0.0094 (5) | −0.0006 (4) | 0.0083 (5) |
| Cu1 | 0.0302 (2) | 0.0355 (2) | 0.0352 (2) | −0.00629 (15) | 0.00768 (16) | 0.01242 (16) |
| N1 | 0.0374 (15) | 0.0360 (14) | 0.0452 (16) | −0.0081 (11) | 0.0110 (13) | 0.0148 (12) |
| N2 | 0.0462 (16) | 0.0438 (16) | 0.0524 (17) | −0.0043 (13) | 0.0258 (14) | 0.0084 (13) |
| N3 | 0.0291 (13) | 0.0331 (14) | 0.0389 (15) | −0.0021 (11) | 0.0132 (12) | 0.0117 (11) |
| N4 | 0.0418 (15) | 0.0427 (15) | 0.0434 (16) | −0.0038 (12) | 0.0200 (13) | 0.0111 (12) |
| O1 | 0.0332 (12) | 0.0422 (12) | 0.0407 (12) | −0.0090 (9) | 0.0055 (10) | 0.0162 (10) |
| O2 | 0.0380 (12) | 0.0374 (12) | 0.0393 (12) | −0.0055 (9) | 0.0054 (10) | 0.0142 (10) |
| C1—C2 | 1.359 (4) | C14—C15 | 1.370 (4) |
| C1—C6 | 1.393 (4) | C14—Cl3 | 1.737 (3) |
| C1—Cl2 | 1.745 (3) | C15—C16 | 1.393 (4) |
| C2—C3 | 1.403 (4) | C15—H15 | 0.9300 |
| C2—H2 | 0.9300 | C16—C17 | 1.365 (4) |
| C3—C4 | 1.423 (4) | C16—Cl4 | 1.745 (3) |
| C3—C7 | 1.445 (4) | C17—C18 | 1.401 (4) |
| C4—O1 | 1.298 (3) | C17—H17 | 0.9300 |
| C4—C5 | 1.419 (4) | C18—C19 | 1.446 (4) |
| C5—C6 | 1.375 (4) | C19—N3 | 1.284 (4) |
| C5—Cl1 | 1.743 (3) | C19—H19 | 0.9300 |
| C6—H6 | 0.9300 | C20—N3 | 1.488 (3) |
| C7—N1 | 1.272 (4) | C20—C21 | 1.527 (4) |
| C7—H7 | 0.9300 | C20—H20A | 0.9700 |
| C8—N1 | 1.470 (3) | C20—H20B | 0.9700 |
| C8—C9 | 1.527 (5) | C21—C22 | 1.510 (4) |
| C8—H8A | 0.9700 | C21—H21A | 0.9700 |
| C8—H8B | 0.9700 | C21—H21B | 0.9700 |
| C9—C10 | 1.514 (5) | C22—N4 | 1.461 (4) |
| C9—H9A | 0.9700 | C22—H22A | 0.9700 |
| C9—H9B | 0.9700 | C22—H22B | 0.9700 |
| C10—N2 | 1.485 (4) | C23—N4 | 1.459 (4) |
| C10—H10A | 0.9700 | C23—H23A | 0.9600 |
| C10—H10B | 0.9700 | C23—H23B | 0.9600 |
| C11—N2 | 1.470 (4) | C23—H23C | 0.9600 |
| C11—H11A | 0.9600 | C24—N4 | 1.456 (4) |
| C11—H11B | 0.9600 | C24—H24A | 0.9600 |
| C11—H11C | 0.9600 | C24—H24B | 0.9600 |
| C12—N2 | 1.462 (4) | C24—H24C | 0.9600 |
| C12—H12A | 0.9600 | Cu1—O2 | 1.921 (2) |
| C12—H12B | 0.9600 | Cu1—O1 | 1.924 (2) |
| C12—H12C | 0.9600 | Cu1—N1 | 2.003 (2) |
| C13—O2 | 1.285 (3) | Cu1—N3 | 2.009 (2) |
| C13—C14 | 1.421 (4) | Cu1—N2 | 2.459 (3) |
| C13—C18 | 1.427 (4) | ||
| C2—C1—C6 | 120.5 (3) | C18—C17—H17 | 119.7 |
| C2—C1—Cl2 | 120.5 (3) | C17—C18—C13 | 120.9 (3) |
| C6—C1—Cl2 | 119.0 (2) | C17—C18—C19 | 117.9 (3) |
| C1—C2—C3 | 120.7 (3) | C13—C18—C19 | 121.2 (3) |
| C1—C2—H2 | 119.6 | N3—C19—C18 | 126.9 (3) |
| C3—C2—H2 | 119.6 | N3—C19—H19 | 116.5 |
| C2—C3—C4 | 121.1 (3) | C18—C19—H19 | 116.5 |
| C2—C3—C7 | 117.7 (3) | N3—C20—C21 | 110.5 (2) |
| C4—C3—C7 | 121.0 (3) | N3—C20—H20A | 109.5 |
| O1—C4—C5 | 120.5 (3) | C21—C20—H20A | 109.5 |
| O1—C4—C3 | 124.4 (3) | N3—C20—H20B | 109.5 |
| C5—C4—C3 | 115.1 (3) | C21—C20—H20B | 109.5 |
| C6—C5—C4 | 123.4 (3) | H20A—C20—H20B | 108.1 |
| C6—C5—Cl1 | 118.8 (2) | C22—C21—C20 | 114.1 (3) |
| C4—C5—Cl1 | 117.7 (2) | C22—C21—H21A | 108.7 |
| C5—C6—C1 | 119.0 (3) | C20—C21—H21A | 108.7 |
| C5—C6—H6 | 120.5 | C22—C21—H21B | 108.7 |
| C1—C6—H6 | 120.5 | C20—C21—H21B | 108.7 |
| N1—C7—C3 | 126.8 (3) | H21A—C21—H21B | 107.6 |
| N1—C7—H7 | 116.6 | N4—C22—C21 | 112.6 (3) |
| C3—C7—H7 | 116.6 | N4—C22—H22A | 109.1 |
| N1—C8—C9 | 110.1 (3) | C21—C22—H22A | 109.1 |
| N1—C8—H8A | 109.6 | N4—C22—H22B | 109.1 |
| C9—C8—H8A | 109.6 | C21—C22—H22B | 109.1 |
| N1—C8—H8B | 109.6 | H22A—C22—H22B | 107.8 |
| C9—C8—H8B | 109.6 | N4—C23—H23A | 109.5 |
| H8A—C8—H8B | 108.2 | N4—C23—H23B | 109.5 |
| C10—C9—C8 | 117.6 (3) | H23A—C23—H23B | 109.5 |
| C10—C9—H9A | 107.9 | N4—C23—H23C | 109.5 |
| C8—C9—H9A | 107.9 | H23A—C23—H23C | 109.5 |
| C10—C9—H9B | 107.9 | H23B—C23—H23C | 109.5 |
| C8—C9—H9B | 107.9 | N4—C24—H24A | 109.5 |
| H9A—C9—H9B | 107.2 | N4—C24—H24B | 109.5 |
| N2—C10—C9 | 115.5 (3) | H24A—C24—H24B | 109.5 |
| N2—C10—H10A | 108.4 | N4—C24—H24C | 109.5 |
| C9—C10—H10A | 108.4 | H24A—C24—H24C | 109.5 |
| N2—C10—H10B | 108.4 | H24B—C24—H24C | 109.5 |
| C9—C10—H10B | 108.4 | O2—Cu1—O1 | 173.30 (9) |
| H10A—C10—H10B | 107.5 | O2—Cu1—N1 | 89.22 (9) |
| N2—C11—H11A | 109.5 | O1—Cu1—N1 | 90.08 (9) |
| N2—C11—H11B | 109.5 | O2—Cu1—N3 | 90.21 (9) |
| H11A—C11—H11B | 109.5 | O1—Cu1—N3 | 89.49 (9) |
| N2—C11—H11C | 109.5 | N1—Cu1—N3 | 171.46 (10) |
| H11A—C11—H11C | 109.5 | O2—Cu1—N2 | 87.36 (9) |
| H11B—C11—H11C | 109.5 | O1—Cu1—N2 | 99.17 (9) |
| N2—C12—H12A | 109.5 | N1—Cu1—N2 | 82.79 (10) |
| N2—C12—H12B | 109.5 | N3—Cu1—N2 | 105.69 (9) |
| H12A—C12—H12B | 109.5 | C7—N1—C8 | 116.5 (3) |
| N2—C12—H12C | 109.5 | C7—N1—Cu1 | 125.1 (2) |
| H12A—C12—H12C | 109.5 | C8—N1—Cu1 | 118.3 (2) |
| H12B—C12—H12C | 109.5 | C12—N2—C11 | 109.4 (3) |
| O2—C13—C14 | 120.6 (3) | C12—N2—C10 | 108.9 (3) |
| O2—C13—C18 | 124.1 (3) | C11—N2—C10 | 111.1 (3) |
| C14—C13—C18 | 115.3 (3) | C12—N2—Cu1 | 110.2 (2) |
| C15—C14—C13 | 123.3 (3) | C11—N2—Cu1 | 107.1 (2) |
| C15—C14—Cl3 | 118.8 (2) | C10—N2—Cu1 | 110.2 (2) |
| C13—C14—Cl3 | 117.9 (2) | C19—N3—C20 | 114.8 (2) |
| C14—C15—C16 | 119.1 (3) | C19—N3—Cu1 | 124.33 (19) |
| C14—C15—H15 | 120.4 | C20—N3—Cu1 | 120.80 (18) |
| C16—C15—H15 | 120.4 | C24—N4—C23 | 110.6 (3) |
| C17—C16—C15 | 120.7 (3) | C24—N4—C22 | 111.8 (3) |
| C17—C16—Cl4 | 121.0 (3) | C23—N4—C22 | 111.9 (3) |
| C15—C16—Cl4 | 118.3 (2) | C4—O1—Cu1 | 128.22 (18) |
| C16—C17—C18 | 120.6 (3) | C13—O2—Cu1 | 128.34 (18) |
| C16—C17—H17 | 119.7 |
| Cu1—O2 | 1.921 (2) | Cu1—N3 | 2.009 (2) |
| Cu1—O1 | 1.924 (2) | Cu1—N2 | 2.459 (3) |
| Cu1—N1 | 2.003 (2) |
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![[Figure 1]](./hb5109fig1thm.gif)
There has been much research interest in Schiff base metal complexes due to their molecular architectures and biological activities (Shi et al., 2007; Shi et al., 2008). In this work, we report here the crystal structure of the title compound, (I). In (I), all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). The CuII is coordinated by two O and three N atoms from the two Schiff base ligands, forming a distorted square-pyramidal coordination (Table 1).