metal-organic compounds
The title compound, [CuCl2(C10H9NO)2], has crystallographically imposed twofold symmetry. The Cu atom is surrounded by two Cl atoms and two O atoms in a distorted square-planar configuration.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804012942/su6105sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804012942/su6105Isup2.hkl |
CCDC reference: 245108
Computing details top
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: DIRDIF96 (Beurkens et al., 1996); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
[CuCl2(C20H18N2O2)] | Dx = 1.555 Mg m−3 |
Mr = 452.80 | Melting point: 493(1) K |
Orthorhombic, Pccn | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2ab 2ac | Cell parameters from 25 reflections |
a = 7.332 (3) Å | θ = 22–25° |
b = 15.185 (5) Å | µ = 4.29 mm−1 |
c = 17.370 (6) Å | T = 293 K |
V = 1933.8 (12) Å3 | Plate, brown |
Z = 4 | 0.08 × 0.06 × 0.02 mm |
F(000) = 924 |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.000 |
Radiation source: Fine–focus sealed tube | θmax = 74.9°, θmin = 5.1° |
Graphite monochromator | h = −8→0 |
Non–profiled ω/2θ scans | k = 0→19 |
1952 measured reflections | l = 0→21 |
1952 independent reflections | 1 standard reflections every 60 min |
1046 reflections with I > 2σ(I) | intensity decay: 3% |
Refinement top
Refinement on F2 | Primary atom site location: Heavy |
Least-squares matrix: Full | Secondary atom site location: Difmap |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: Geom |
wR(F2) = 0.062 | Only H-atom displacement parameters refined |
S = 0.88 | w = 1/[σ2(Fo2) + (0.007P)2] where P = (Fo2 + 2Fc2)/3 |
1952 reflections | (Δ/σ)max = 0.001 |
132 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Special details top
Experimental. The IR spectra were recorded in KBr using Specord M–80 spectrometer. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cu | 0.7500 | 0.2500 | 0.09036 (4) | 0.0399 (2) | |
Cl | 0.79478 (15) | 0.39336 (6) | 0.07365 (7) | 0.0644 (4) | |
O1 | 0.4842 (3) | 0.2602 (2) | 0.10338 (14) | 0.0507 (7) | |
N1 | 0.4279 (4) | 0.3266 (2) | 0.1490 (2) | 0.0459 (9) | |
C2 | 0.3518 (6) | 0.3965 (3) | 0.1170 (3) | 0.0576 (13) | |
C3 | 0.3007 (6) | 0.4663 (3) | 0.1664 (3) | 0.0668 (15) | |
H3 | 0.2441 | 0.5156 | 0.1455 | 0.086 (15)* | |
C4 | 0.3312 (6) | 0.4633 (3) | 0.2422 (3) | 0.0695 (16) | |
H4 | 0.3061 | 0.5123 | 0.2725 | 0.068 (14)* | |
C5 | 0.4284 (7) | 0.3761 (4) | 0.3564 (3) | 0.0723 (16) | |
H5 | 0.4048 | 0.4229 | 0.3895 | 0.089 (18)* | |
C6 | 0.4885 (6) | 0.2988 (4) | 0.3848 (3) | 0.0769 (18) | |
H6 | 0.5051 | 0.2927 | 0.4376 | 0.10 (2)* | |
C7 | 0.5264 (6) | 0.2278 (3) | 0.3365 (3) | 0.0684 (16) | |
H7 | 0.5631 | 0.1744 | 0.3576 | 0.046 (13)* | |
C8 | 0.5098 (5) | 0.2362 (3) | 0.2575 (3) | 0.0508 (12) | |
H8 | 0.5387 | 0.1896 | 0.2250 | 0.036 (12)* | |
C9 | 0.4489 (5) | 0.3156 (3) | 0.2279 (3) | 0.0444 (11) | |
C10 | 0.4011 (6) | 0.3860 (3) | 0.2763 (3) | 0.0574 (13) | |
C11 | 0.3215 (8) | 0.3969 (4) | 0.0331 (3) | 0.0725 (16) | |
H11A | 0.4368 | 0.4007 | 0.0071 | 0.089 (19)* | |
H11B | 0.2476 | 0.4467 | 0.0195 | 0.083 (16)* | |
H11C | 0.2605 | 0.3436 | 0.0181 | 0.11 (2)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu | 0.0434 (5) | 0.0431 (4) | 0.0333 (4) | 0.0054 (5) | 0.000 | 0.000 |
Cl | 0.0605 (8) | 0.0470 (5) | 0.0857 (9) | 0.0026 (5) | 0.0022 (7) | 0.0081 (6) |
O1 | 0.0540 (17) | 0.0482 (16) | 0.0500 (17) | 0.0032 (15) | −0.0025 (15) | −0.0112 (18) |
N1 | 0.036 (2) | 0.0463 (18) | 0.055 (3) | 0.0009 (16) | −0.001 (2) | −0.007 (2) |
C2 | 0.040 (3) | 0.064 (3) | 0.069 (3) | 0.011 (2) | −0.006 (3) | 0.000 (3) |
C3 | 0.045 (3) | 0.056 (3) | 0.099 (4) | 0.010 (2) | −0.004 (3) | −0.001 (3) |
C4 | 0.055 (3) | 0.064 (3) | 0.090 (4) | 0.000 (3) | 0.003 (3) | −0.023 (4) |
C5 | 0.065 (4) | 0.096 (4) | 0.056 (4) | −0.020 (3) | 0.017 (3) | −0.021 (4) |
C6 | 0.057 (4) | 0.120 (5) | 0.053 (4) | −0.014 (4) | 0.010 (3) | −0.010 (3) |
C7 | 0.052 (3) | 0.086 (5) | 0.068 (3) | −0.008 (3) | 0.001 (3) | 0.013 (3) |
C8 | 0.040 (3) | 0.058 (3) | 0.054 (3) | 0.003 (2) | 0.004 (2) | 0.005 (3) |
C9 | 0.030 (2) | 0.059 (3) | 0.044 (3) | 0.001 (2) | 0.008 (2) | −0.006 (2) |
C10 | 0.042 (3) | 0.066 (3) | 0.064 (3) | −0.013 (3) | 0.014 (3) | −0.015 (3) |
C11 | 0.072 (4) | 0.077 (4) | 0.069 (4) | 0.007 (3) | −0.014 (3) | 0.017 (3) |
Geometric parameters (Å, º) top
Cu—O1i | 1.968 (3) | C5—C6 | 1.348 (6) |
Cu—O1 | 1.968 (3) | C5—C10 | 1.414 (6) |
Cu—Cli | 2.2206 (11) | C5—H5 | 0.9300 |
Cu—Cl | 2.2206 (11) | C6—C7 | 1.394 (6) |
O1—N1 | 1.348 (4) | C6—H6 | 0.9299 |
N1—C2 | 1.322 (5) | C7—C8 | 1.384 (6) |
N1—C9 | 1.389 (5) | C7—H7 | 0.9300 |
C2—C3 | 1.414 (5) | C8—C9 | 1.385 (5) |
C2—C11 | 1.473 (5) | C8—H8 | 0.9300 |
C3—C4 | 1.336 (6) | C9—C10 | 1.404 (5) |
C3—H3 | 0.9300 | C11—H11A | 0.9600 |
C4—C10 | 1.412 (6) | C11—H11B | 0.9600 |
C4—H4 | 0.9300 | C11—H11C | 0.9600 |
O1i—Cu—O1 | 166.80 (16) | C5—C6—C7 | 121.3 (6) |
O1i—Cu—Cli | 94.83 (10) | C5—C6—H6 | 119.3 |
O1—Cu—Cli | 86.89 (10) | C7—C6—H6 | 119.4 |
O1i—Cu—Cl | 86.89 (10) | C8—C7—C6 | 120.5 (5) |
O1—Cu—Cl | 94.83 (10) | C8—C7—H7 | 119.8 |
Cli—Cu—Cl | 164.97 (7) | C6—C7—H7 | 119.7 |
N1—O1—Cu | 115.5 (2) | C7—C8—C9 | 118.5 (5) |
C2—N1—O1 | 118.8 (4) | C7—C8—H8 | 120.9 |
C2—N1—C9 | 124.0 (4) | C9—C8—H8 | 120.6 |
O1—N1—C9 | 117.1 (3) | C8—C9—N1 | 120.5 (4) |
N1—C2—C3 | 117.2 (5) | C8—C9—C10 | 121.4 (4) |
N1—C2—C11 | 118.9 (5) | N1—C9—C10 | 118.1 (4) |
C3—C2—C11 | 123.9 (5) | C9—C10—C4 | 118.2 (5) |
C4—C3—C2 | 121.9 (5) | C9—C10—C5 | 118.3 (5) |
C4—C3—H3 | 119.1 | C4—C10—C5 | 123.6 (5) |
C2—C3—H3 | 119.1 | C2—C11—H11A | 109.4 |
C3—C4—C10 | 120.2 (5) | C2—C11—H11B | 109.4 |
C3—C4—H4 | 119.9 | H11A—C11—H11B | 109.5 |
C10—C4—H4 | 119.9 | C2—C11—H11C | 109.6 |
C6—C5—C10 | 119.9 (6) | H11A—C11—H11C | 109.5 |
C6—C5—H5 | 120.0 | H11B—C11—H11C | 109.5 |
C10—C5—H5 | 120.1 | ||
Cl1—Cu—O1—N1 | −44.0 (3) | Cu—O1—N1—C2 | 106.6 (4) |
Symmetry code: (i) −x+3/2, −y+1/2, z. |