The title compound, [Cu2Cl4(C20H18N2O)2], is a centrosymmetric dimer bridged through the Cl atoms. The bridging Cu2Cl2 unit is planar and each CuII ion has two different distances to the bridging Cl atom. The CuII ions are coordinated to three Cl and two N atoms in a square-pyramidal disposition. Hydrogen bonds are formed by –OH and –NH with the Cl atoms.
Supporting information
CCDC reference: 175978
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.027
- wR factor = 0.062
- Data-to-parameter ratio = 15.5
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced
by the scaled T values. Since the ratio of scaled T's is
identical to the ratio of reported T values, the scaling does
not imply a change to the absorption corrections used in the
study.
Ratio of Tmax expected/reported 0.597
Tmax scaled 0.597 Tmin scaled 0.502
Compound (I) was obtained by slow addition of 30 ml of an absolute ethanol
solution (0.001 M) of 1,2-diphenyl-2-phenylamine-ethanoxime to 30 ml of
an absolute ethanol solution (0.001 M) of CuCl2·2H2O. The
resulting green precipitate was left overnight, filtered and washed several
times with water, followed by ethanol and ether. Recrystallization from
absolute ethanol after drying in vacuum gave crystals suitable for X-ray
structural analysis; m.p. 456–457 K.
All H atoms were located in difference Fourier maps and refined freely except
the H atom bonded to O1, which was calculated in an ideal position and refined
using a riding model via the SHELXL97 HFIX 83 facility.
Data collection: SHELXTL (Bruker, 1997) [AUTHOR: was SHELXTL really used for data collection,
cell refinement and data reduction ?]; cell refinement: SHELXTL; data reduction: SHELXTL; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Di-µ-chloro-bis{chloro[1,2-diphenyl-2-(phenylamino)ethanoximato]copper(II)}
top
Crystal data top
[Cu2Cl4(C20H18N2O)2] | Dx = 1.561 Mg m−3 |
Mr = 873.61 | Melting point = 456–457 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.1739 (3) Å | Cell parameters from 6428 reflections |
b = 22.1696 (7) Å | θ = 2.4–28.5° |
c = 9.4404 (3) Å | µ = 1.47 mm−1 |
β = 104.592 (1)° | T = 100 K |
V = 1858.07 (10) Å3 | Rhombohedral, dark-green |
Z = 2 | 0.42 × 0.38 × 0.35 mm |
F(000) = 892 | |
Data collection top
Bruker SMART CCD 1K area-detector diffractometer | 4707 independent reflections |
Radiation source: fine-focus sealed tube | 4187 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 8 pixels mm-1 | θmax = 28.5°, θmin = 1.8° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −29→29 |
Tmin = 0.842, Tmax = 1.000 | l = −12→12 |
21701 measured reflections | |
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)] = 0.027 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.063 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0227P)2 + 1.7471P] where P = (Fo2 + 2Fc2)/3 |
4707 reflections | (Δ/σ)max = 0.008 |
303 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
Crystal data top
[Cu2Cl4(C20H18N2O)2] | V = 1858.07 (10) Å3 |
Mr = 873.61 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.1739 (3) Å | µ = 1.47 mm−1 |
b = 22.1696 (7) Å | T = 100 K |
c = 9.4404 (3) Å | 0.42 × 0.38 × 0.35 mm |
β = 104.592 (1)° | |
Data collection top
Bruker SMART CCD 1K area-detector diffractometer | 4707 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4187 reflections with I > 2σ(I) |
Tmin = 0.842, Tmax = 1.000 | Rint = 0.027 |
21701 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.027 | 0 restraints |
wR(F2) = 0.063 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.45 e Å−3 |
4707 reflections | Δρmin = −0.40 e Å−3 |
303 parameters | |
Special details top
Experimental. The data collection nominally covered full sphere of reciprocal Space, by a
combination of 5 sets of ω scans each set at different ϕ and/or 2θ angles
and each scan (25 s exposure) covering 0.3° in ω. Crystal to detector
distance 4.51 cm. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.17994 (2) | 0.033141 (8) | 0.04072 (2) | 0.01209 (6) | |
Cl1 | −0.05756 (4) | 0.018429 (18) | −0.18538 (4) | 0.01537 (8) | |
Cl2 | 0.31650 (4) | −0.045273 (17) | −0.00170 (5) | 0.01608 (8) | |
O1 | −0.02507 (13) | 0.12175 (5) | 0.13696 (13) | 0.0167 (2) | |
H1 | −0.0747 | 0.0895 | 0.1260 | 0.025* | |
N1 | 0.31781 (16) | 0.09236 (6) | −0.03444 (15) | 0.0132 (3) | |
N2 | 0.10730 (15) | 0.11295 (6) | 0.09524 (15) | 0.0131 (3) | |
C1 | 0.34128 (18) | 0.14598 (7) | 0.06463 (18) | 0.0140 (3) | |
C2 | 0.19444 (18) | 0.15914 (7) | 0.10667 (17) | 0.0129 (3) | |
C3 | 0.47135 (18) | 0.13359 (7) | 0.19754 (18) | 0.0152 (3) | |
C4 | 0.4560 (2) | 0.09314 (8) | 0.30557 (19) | 0.0186 (3) | |
C5 | 0.5784 (2) | 0.08049 (9) | 0.4230 (2) | 0.0225 (4) | |
C6 | 0.7157 (2) | 0.10865 (9) | 0.4334 (2) | 0.0238 (4) | |
C7 | 0.7308 (2) | 0.14934 (9) | 0.3269 (2) | 0.0228 (4) | |
C8 | 0.6092 (2) | 0.16166 (8) | 0.2086 (2) | 0.0191 (3) | |
C9 | 0.16510 (19) | 0.22071 (7) | 0.15414 (18) | 0.0145 (3) | |
C10 | 0.0205 (2) | 0.24575 (8) | 0.1131 (2) | 0.0186 (3) | |
C11 | −0.0031 (2) | 0.30448 (8) | 0.1526 (2) | 0.0212 (4) | |
C12 | 0.1153 (2) | 0.33832 (8) | 0.2355 (2) | 0.0209 (4) | |
C13 | 0.2584 (2) | 0.31401 (8) | 0.2761 (2) | 0.0226 (4) | |
C14 | 0.2844 (2) | 0.25564 (8) | 0.2352 (2) | 0.0196 (4) | |
C15 | 0.25378 (18) | 0.10360 (7) | −0.18925 (18) | 0.0145 (3) | |
C16 | 0.16326 (19) | 0.15342 (8) | −0.2383 (2) | 0.0177 (3) | |
C17 | 0.0977 (2) | 0.15973 (9) | −0.3881 (2) | 0.0211 (4) | |
C18 | 0.1210 (2) | 0.11698 (9) | −0.4864 (2) | 0.0215 (4) | |
C19 | 0.2114 (2) | 0.06716 (8) | −0.4356 (2) | 0.0199 (3) | |
C20 | 0.2789 (2) | 0.06052 (8) | −0.28719 (19) | 0.0172 (3) | |
H2 | 0.400 (2) | 0.0746 (9) | −0.019 (2) | 0.014 (5)* | |
H3 | 0.364 (2) | 0.1803 (9) | 0.011 (2) | 0.009 (4)* | |
H4 | 0.363 (3) | 0.0753 (10) | 0.304 (2) | 0.021 (5)* | |
H5 | 0.566 (3) | 0.0540 (11) | 0.494 (3) | 0.026 (6)* | |
H6 | 0.796 (3) | 0.1007 (10) | 0.510 (3) | 0.026 (6)* | |
H7 | 0.822 (3) | 0.1684 (10) | 0.331 (2) | 0.023 (6)* | |
H8 | 0.619 (2) | 0.1876 (10) | 0.135 (2) | 0.020 (5)* | |
H9 | −0.059 (2) | 0.2231 (10) | 0.060 (2) | 0.019 (5)* | |
H10 | −0.102 (3) | 0.3208 (10) | 0.122 (2) | 0.025 (6)* | |
H11 | 0.097 (3) | 0.3785 (11) | 0.264 (3) | 0.030 (6)* | |
H12 | 0.336 (3) | 0.3373 (10) | 0.329 (3) | 0.025 (6)* | |
H13 | 0.385 (3) | 0.2396 (10) | 0.261 (2) | 0.022 (5)* | |
H14 | 0.146 (2) | 0.1838 (10) | −0.174 (2) | 0.022 (5)* | |
H15 | 0.038 (3) | 0.1932 (10) | −0.421 (2) | 0.025 (6)* | |
H16 | 0.075 (2) | 0.1208 (10) | −0.589 (2) | 0.023 (6)* | |
H17 | 0.225 (3) | 0.0371 (10) | −0.506 (3) | 0.025 (6)* | |
H18 | 0.338 (2) | 0.0250 (10) | −0.254 (2) | 0.022 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.01278 (10) | 0.01011 (9) | 0.01385 (10) | −0.00086 (7) | 0.00420 (7) | −0.00073 (7) |
Cl1 | 0.01524 (18) | 0.01635 (18) | 0.01429 (18) | −0.00248 (13) | 0.00332 (14) | 0.00197 (13) |
Cl2 | 0.01434 (18) | 0.01154 (17) | 0.0226 (2) | 0.00126 (13) | 0.00510 (15) | 0.00041 (14) |
O1 | 0.0127 (6) | 0.0170 (6) | 0.0228 (6) | −0.0030 (4) | 0.0089 (5) | −0.0045 (5) |
N1 | 0.0130 (7) | 0.0111 (6) | 0.0156 (7) | 0.0011 (5) | 0.0035 (5) | −0.0012 (5) |
N2 | 0.0114 (6) | 0.0156 (6) | 0.0129 (6) | 0.0003 (5) | 0.0043 (5) | −0.0012 (5) |
C1 | 0.0134 (7) | 0.0122 (7) | 0.0162 (8) | −0.0008 (6) | 0.0034 (6) | −0.0016 (6) |
C2 | 0.0119 (7) | 0.0135 (7) | 0.0126 (7) | 0.0009 (5) | 0.0017 (6) | −0.0004 (6) |
C3 | 0.0135 (8) | 0.0159 (7) | 0.0159 (8) | 0.0011 (6) | 0.0031 (6) | −0.0044 (6) |
C4 | 0.0150 (8) | 0.0219 (8) | 0.0181 (8) | −0.0012 (6) | 0.0026 (7) | −0.0017 (7) |
C5 | 0.0221 (9) | 0.0242 (9) | 0.0190 (9) | 0.0026 (7) | 0.0010 (7) | −0.0003 (7) |
C6 | 0.0169 (9) | 0.0313 (10) | 0.0195 (9) | 0.0043 (7) | −0.0021 (7) | −0.0062 (7) |
C7 | 0.0124 (8) | 0.0300 (10) | 0.0247 (9) | −0.0011 (7) | 0.0025 (7) | −0.0085 (7) |
C8 | 0.0152 (8) | 0.0224 (9) | 0.0203 (9) | −0.0009 (6) | 0.0055 (7) | −0.0029 (7) |
C9 | 0.0160 (8) | 0.0119 (7) | 0.0158 (8) | 0.0003 (6) | 0.0045 (6) | −0.0011 (6) |
C10 | 0.0145 (8) | 0.0179 (8) | 0.0221 (9) | 0.0001 (6) | 0.0020 (7) | −0.0036 (7) |
C11 | 0.0176 (9) | 0.0194 (9) | 0.0265 (9) | 0.0052 (7) | 0.0054 (7) | −0.0016 (7) |
C12 | 0.0265 (9) | 0.0145 (8) | 0.0211 (9) | 0.0029 (7) | 0.0047 (7) | −0.0045 (6) |
C13 | 0.0217 (9) | 0.0181 (8) | 0.0233 (9) | −0.0017 (7) | −0.0031 (7) | −0.0050 (7) |
C14 | 0.0149 (8) | 0.0168 (8) | 0.0248 (9) | 0.0009 (6) | 0.0005 (7) | −0.0028 (7) |
C15 | 0.0099 (7) | 0.0179 (8) | 0.0156 (8) | −0.0033 (6) | 0.0031 (6) | 0.0016 (6) |
C16 | 0.0154 (8) | 0.0193 (8) | 0.0187 (8) | 0.0000 (6) | 0.0048 (7) | −0.0006 (6) |
C17 | 0.0145 (8) | 0.0268 (9) | 0.0206 (9) | 0.0036 (7) | 0.0017 (7) | 0.0041 (7) |
C18 | 0.0158 (8) | 0.0330 (10) | 0.0141 (8) | −0.0017 (7) | 0.0008 (7) | 0.0017 (7) |
C19 | 0.0190 (8) | 0.0238 (9) | 0.0175 (8) | −0.0037 (7) | 0.0056 (7) | −0.0020 (7) |
C20 | 0.0172 (8) | 0.0175 (8) | 0.0174 (8) | −0.0009 (6) | 0.0053 (7) | 0.0010 (6) |
Geometric parameters (Å, º) top
Cu1—N2 | 2.0031 (14) | C7—C8 | 1.392 (3) |
Cu1—N1 | 2.0686 (14) | C7—H7 | 0.93 (2) |
Cu1—Cl2 | 2.2371 (4) | C8—H8 | 0.93 (2) |
Cu1—Cl1i | 2.2814 (4) | C9—C10 | 1.399 (2) |
Cu1—Cl1 | 2.6582 (4) | C9—C14 | 1.400 (2) |
Cu1—Cu1i | 3.5172 (4) | C10—C11 | 1.386 (2) |
Cl1—Cu1i | 2.2814 (4) | C10—H9 | 0.92 (2) |
O1—N2 | 1.3816 (17) | C11—C12 | 1.388 (3) |
O1—H1 | 0.8400 | C11—H10 | 0.95 (2) |
N1—C15 | 1.453 (2) | C12—C13 | 1.380 (3) |
N1—C1 | 1.494 (2) | C12—H11 | 0.96 (2) |
N1—H2 | 0.83 (2) | C13—C14 | 1.388 (2) |
N2—C2 | 1.287 (2) | C13—H12 | 0.92 (2) |
C1—C3 | 1.523 (2) | C14—H13 | 0.96 (2) |
C1—C2 | 1.525 (2) | C15—C20 | 1.388 (2) |
C1—H3 | 0.964 (19) | C15—C16 | 1.389 (2) |
C2—C9 | 1.482 (2) | C16—C17 | 1.397 (3) |
C3—C8 | 1.390 (2) | C16—H14 | 0.95 (2) |
C3—C4 | 1.392 (2) | C17—C18 | 1.380 (3) |
C4—C5 | 1.393 (3) | C17—H15 | 0.93 (2) |
C4—H4 | 0.94 (2) | C18—C19 | 1.392 (3) |
C5—C6 | 1.387 (3) | C18—H16 | 0.96 (2) |
C5—H5 | 0.92 (2) | C19—C20 | 1.390 (2) |
C6—C7 | 1.383 (3) | C19—H17 | 0.97 (2) |
C6—H6 | 0.91 (2) | C20—H18 | 0.97 (2) |
| | | |
N2—Cu1—N1 | 78.42 (5) | C5—C6—H6 | 120.4 (15) |
N2—Cu1—Cl2 | 165.92 (4) | C6—C7—C8 | 120.28 (17) |
N1—Cu1—Cl2 | 90.77 (4) | C6—C7—H7 | 121.2 (14) |
N2—Cu1—Cl1i | 92.47 (4) | C8—C7—H7 | 118.5 (14) |
N1—Cu1—Cl1i | 163.53 (4) | C3—C8—C7 | 120.16 (18) |
Cl2—Cu1—Cl1i | 95.736 (16) | C3—C8—H8 | 118.8 (13) |
N2—Cu1—Cl1 | 93.23 (4) | C7—C8—H8 | 121.0 (13) |
N1—Cu1—Cl1 | 104.52 (4) | C10—C9—C14 | 119.18 (15) |
Cl2—Cu1—Cl1 | 98.258 (15) | C10—C9—C2 | 120.87 (15) |
Cl1i—Cu1—Cl1 | 89.528 (15) | C14—C9—C2 | 119.87 (15) |
N2—Cu1—Cu1i | 94.04 (4) | C11—C10—C9 | 119.96 (16) |
N1—Cu1—Cu1i | 144.25 (4) | C11—C10—H9 | 120.0 (13) |
Cl2—Cu1—Cu1i | 99.984 (13) | C9—C10—H9 | 120.0 (13) |
Cu1i—Cl1—Cu1 | 90.472 (15) | C10—C11—C12 | 120.41 (17) |
N2—O1—H1 | 109.5 | C10—C11—H10 | 118.5 (14) |
C15—N1—C1 | 116.82 (13) | C12—C11—H10 | 121.1 (14) |
C15—N1—Cu1 | 109.07 (10) | C13—C12—C11 | 119.97 (16) |
C1—N1—Cu1 | 107.11 (10) | C13—C12—H11 | 120.7 (14) |
C15—N1—H2 | 111.9 (14) | C11—C12—H11 | 119.3 (14) |
C1—N1—H2 | 106.8 (14) | C12—C13—C14 | 120.30 (17) |
Cu1—N1—H2 | 104.3 (14) | C12—C13—H12 | 119.0 (14) |
C2—N2—O1 | 115.84 (13) | C14—C13—H12 | 120.7 (14) |
C2—N2—Cu1 | 118.98 (11) | C13—C14—C9 | 120.15 (16) |
O1—N2—Cu1 | 124.84 (10) | C13—C14—H13 | 119.7 (13) |
N1—C1—C3 | 109.38 (13) | C9—C14—H13 | 120.1 (13) |
N1—C1—C2 | 108.52 (13) | C20—C15—C16 | 120.71 (16) |
C3—C1—C2 | 112.34 (13) | C20—C15—N1 | 117.32 (15) |
N1—C1—H3 | 108.5 (11) | C16—C15—N1 | 121.85 (15) |
C3—C1—H3 | 110.2 (11) | C15—C16—C17 | 119.03 (17) |
C2—C1—H3 | 107.8 (11) | C15—C16—H14 | 122.2 (13) |
N2—C2—C9 | 127.00 (15) | C17—C16—H14 | 118.8 (13) |
N2—C2—C1 | 113.37 (14) | C18—C17—C16 | 120.79 (17) |
C9—C2—C1 | 119.63 (14) | C18—C17—H15 | 119.9 (14) |
C8—C3—C4 | 119.45 (16) | C16—C17—H15 | 119.3 (14) |
C8—C3—C1 | 119.38 (15) | C17—C18—C19 | 119.54 (17) |
C4—C3—C1 | 121.14 (15) | C17—C18—H16 | 121.0 (13) |
C3—C4—C5 | 120.16 (17) | C19—C18—H16 | 119.5 (13) |
C3—C4—H4 | 121.3 (13) | C20—C19—C18 | 120.45 (17) |
C5—C4—H4 | 118.5 (13) | C20—C19—H17 | 121.0 (14) |
C6—C5—C4 | 120.10 (18) | C18—C19—H17 | 118.5 (13) |
C6—C5—H5 | 120.9 (14) | C15—C20—C19 | 119.48 (16) |
C4—C5—H5 | 119.0 (14) | C15—C20—H18 | 121.3 (13) |
C7—C6—C5 | 119.84 (18) | C19—C20—H18 | 119.2 (13) |
C7—C6—H6 | 119.8 (15) | | |
Symmetry code: (i) −x, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···Cl2i | 0.84 | 2.44 | 3.1516 (12) | 143 |
O1—H1···Cl1i | 0.84 | 2.68 | 3.2042 (13) | 122 |
N1—H2···Cl2ii | 0.83 (2) | 2.64 (2) | 3.4473 (15) | 164.7 (18) |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y, −z. |
Experimental details
Crystal data |
Chemical formula | [Cu2Cl4(C20H18N2O)2] |
Mr | 873.61 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 9.1739 (3), 22.1696 (7), 9.4404 (3) |
β (°) | 104.592 (1) |
V (Å3) | 1858.07 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.47 |
Crystal size (mm) | 0.42 × 0.38 × 0.35 |
|
Data collection |
Diffractometer | Bruker SMART CCD 1K area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.842, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21701, 4707, 4187 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.671 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.027, 0.063, 1.07 |
No. of reflections | 4707 |
No. of parameters | 303 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.45, −0.40 |
Selected geometric parameters (Å, º) topCu1—N2 | 2.0031 (14) | Cu1—Cl1i | 2.2814 (4) |
Cu1—N1 | 2.0686 (14) | Cu1—Cl1 | 2.6582 (4) |
Cu1—Cl2 | 2.2371 (4) | Cu1—Cu1i | 3.5172 (4) |
| | | |
N2—Cu1—N1 | 78.42 (5) | Cl2—Cu1—Cl1i | 95.736 (16) |
N2—Cu1—Cl2 | 165.92 (4) | N2—Cu1—Cl1 | 93.23 (4) |
N1—Cu1—Cl2 | 90.77 (4) | N1—Cu1—Cl1 | 104.52 (4) |
N2—Cu1—Cl1i | 92.47 (4) | Cl2—Cu1—Cl1 | 98.258 (15) |
N1—Cu1—Cl1i | 163.53 (4) | Cl1i—Cu1—Cl1 | 89.528 (15) |
Symmetry code: (i) −x, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···Cl2i | 0.84 | 2.44 | 3.1516 (12) | 143.2 |
O1—H1···Cl1i | 0.84 | 2.68 | 3.2042 (13) | 122.1 |
N1—H2···Cl2ii | 0.83 (2) | 2.64 (2) | 3.4473 (15) | 164.7 (18) |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y, −z. |
The synthesis and characterization of binuclear copper(II) complexes has made an impact on bio-inorganic chemistry (Solomon et al., 1996). Copper(II) compounds with imidazoles have been used as models to mimic biological systems (Kitajima & Moro-Oka, 1994). Copper(II)–carboxylate adducts with imidazole ligands have a variety of pharmacological properties (Tamura & Imai, 1987). Recently, some attention has been paid to the study of CuII complexes with –N—C—C—N–, which has a flexible backbone that enables it to act as a bis-chelating ligand (Bernhardt & Shape, 1998; Haidar et al., 1997; Urtiaga et al., 1997; Comba et al., 1995). Our study is focused on the determination of the bio-active properties of CuII complexes with –N—C—C═N– ligands. While trying to synthesize CuN4 compounds with that ligand from the reaction of 1,2-diphenyl-2-(phenylamino)ethanoxime with CuCl2 in ethanol, we obtained a new compound of the type Cu2Cl4N4, as shown by the crystallographic study, namely di-µ-chloro-bis{chloro[1,2-diphenyl-2-(phenylamino)ethanoximato]copper(II)}, (I).
The determination of the crystal structure from data recorded at 100 K shows that (I) consists of binuclear molecules with Cl acting as the bridging atoms (Fig. 1). This compound is centrosymmetric with only one half independent molecule per asymmetric unit. Each metal centre has a square-pyramidal coordination. The four short bonds are to two N atoms, a terminal Cl atom and a bridging Cl atom. The long apical bond involves the other bridging Cl atom. So, in (I) there are two types of Cl atoms, bridging and non-bridging.
The bridging Cu2Cl2 unit is planar. The Cu1—Cl1 and Cu1—Cl1i [symmetry code: (i) -x, -y, -z] distances are not equal (Table 1); the larger distance corresponding to the Cl in the apex of the square pyramid and the smaller one to the basal Cl.
The copper–copper distance (Table 1) is similar to the value [3.518 (3) Å] found by Menger et al. (1991) in di-µ-chloro-bis[chloro(2,9-didodecyl-1,10-phenanthroline-N,N')copper], and it is close to the mean copper–copper distance (3.525 Å) found in the di-µ-chloro pentacoordinated CuII complexes registered in the April 2001 version of the Cambridge Structural Database (Allen & Kennard, 1993).
The OH group is involved in a bifurcated hydrogen bond (Jeffrey et al., 1985) with Cl1i and Cl2i, and –NH forms an intermolecular hydrogen bond with Cl2ii [symmetry code: (ii) 1 - x, -y, -z] (Table 2).