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The title complex, [Cu2Cl4(C12H10N2O)2], was synthesized by reacting phenyl 2-pyridyl ketone oxime with CuCl2·2H2O in a basic medium. The organic ligand coordinates to the CuII ions through its N atoms, while the oxime O atom remains uncoordinated. The Cl− ions play two roles: one is a terminal ligand and the other is a bridging ligand, the bridge being formed through a crystallographic inversion centre.
Supporting information
CCDC reference: 620648
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.005 Å
- R factor = 0.043
- wR factor = 0.113
- Data-to-parameter ratio = 18.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.08
PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - N1 .. 5.41 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C5 .. 6.43 su
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2002); cell refinement: SMART; data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Di-µ-chloro-bis[chloro(phenyl 2-pyridyl ketone
oxime-
κ2N,
N')copper(II)]
top
Crystal data top
[Cu2Cl4(C12H10N2O)2] | F(000) = 668.0 |
Mr = 665.34 | Dx = 1.676 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 240 reflections |
a = 10.3137 (14) Å | θ = 2.2–26.0° |
b = 13.8137 (18) Å | µ = 2.05 mm−1 |
c = 9.4334 (13) Å | T = 295 K |
β = 101.218 (2)° | Block, dark green |
V = 1318.3 (3) Å3 | 0.32 × 0.26 × 0.20 mm |
Z = 2 | |
Data collection top
Bruker APEX area-dectector diffractometer | 3010 independent reflections |
Radiation source: fine-focus sealed tube | 2569 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
φ and ω scans | θmax = 27.9°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −10→13 |
Tmin = 0.533, Tmax = 0.664 | k = −18→17 |
8038 measured reflections | l = −12→11 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0569P)2 + 0.7387P] where P = (Fo2 + 2Fc2)/3 |
3010 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.65 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.09623 (3) | 0.40051 (3) | 0.05788 (3) | 0.03991 (14) | |
Cl1 | 0.10583 (8) | 0.59494 (5) | 0.08485 (8) | 0.0495 (2) | |
Cl2 | 0.20546 (9) | 0.38672 (7) | −0.12713 (8) | 0.0581 (2) | |
N1 | 0.2663 (2) | 0.37741 (19) | 0.1968 (2) | 0.0420 (5) | |
N2 | 0.0334 (2) | 0.38333 (17) | 0.2470 (3) | 0.0402 (5) | |
C7 | 0.2665 (3) | 0.3676 (2) | 0.3319 (3) | 0.0377 (6) | |
O1 | 0.3879 (2) | 0.3795 (2) | 0.1560 (3) | 0.0645 (7) | |
H1 | 0.3782 | 0.3957 | 0.0710 | 0.097* | |
C8 | 0.1314 (3) | 0.3698 (2) | 0.3637 (3) | 0.0389 (6) | |
C9 | 0.1039 (3) | 0.3577 (2) | 0.5001 (3) | 0.0481 (7) | |
H13 | 0.1721 | 0.3471 | 0.5789 | 0.058* | |
C1 | 0.3874 (3) | 0.3533 (2) | 0.4427 (3) | 0.0417 (7) | |
C12 | −0.0904 (3) | 0.3862 (2) | 0.2669 (4) | 0.0519 (8) | |
H10 | −0.1577 | 0.3953 | 0.1869 | 0.062* | |
C2 | 0.4768 (3) | 0.2817 (2) | 0.4212 (3) | 0.0491 (7) | |
H2 | 0.4585 | 0.2435 | 0.3386 | 0.059* | |
C6 | 0.4169 (4) | 0.4109 (2) | 0.5651 (3) | 0.0585 (9) | |
H6 | 0.3583 | 0.4588 | 0.5818 | 0.070* | |
C10 | −0.0252 (4) | 0.3614 (3) | 0.5189 (4) | 0.0577 (9) | |
H12 | −0.0451 | 0.3540 | 0.6102 | 0.069* | |
C3 | 0.5918 (3) | 0.2667 (3) | 0.5207 (4) | 0.0655 (10) | |
H3 | 0.6494 | 0.2174 | 0.5066 | 0.079* | |
C11 | −0.1239 (4) | 0.3762 (3) | 0.4007 (4) | 0.0590 (9) | |
H11 | −0.2118 | 0.3796 | 0.4105 | 0.071* | |
C5 | 0.5359 (5) | 0.3963 (3) | 0.6633 (4) | 0.0734 (13) | |
H5 | 0.5573 | 0.4354 | 0.7447 | 0.088* | |
C4 | 0.6207 (4) | 0.3245 (4) | 0.6396 (4) | 0.0733 (12) | |
H4 | 0.6992 | 0.3150 | 0.7058 | 0.088* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0452 (2) | 0.0492 (2) | 0.02348 (19) | 0.00573 (15) | 0.00205 (14) | 0.00104 (13) |
Cl1 | 0.0507 (5) | 0.0516 (4) | 0.0390 (4) | −0.0039 (3) | −0.0086 (3) | −0.0028 (3) |
Cl2 | 0.0709 (6) | 0.0785 (6) | 0.0253 (3) | 0.0202 (4) | 0.0103 (3) | 0.0009 (3) |
N1 | 0.0428 (13) | 0.0583 (14) | 0.0256 (11) | 0.0104 (11) | 0.0085 (9) | −0.0003 (10) |
N2 | 0.0448 (14) | 0.0443 (13) | 0.0320 (12) | 0.0012 (10) | 0.0084 (10) | 0.0036 (9) |
C7 | 0.0464 (16) | 0.0421 (14) | 0.0237 (12) | 0.0050 (12) | 0.0048 (11) | 0.0003 (10) |
O1 | 0.0574 (15) | 0.1032 (19) | 0.0351 (12) | 0.0098 (13) | 0.0142 (10) | 0.0037 (12) |
C8 | 0.0505 (17) | 0.0385 (13) | 0.0279 (13) | 0.0024 (12) | 0.0079 (12) | −0.0005 (10) |
C9 | 0.062 (2) | 0.0545 (17) | 0.0297 (14) | 0.0035 (14) | 0.0120 (13) | 0.0023 (13) |
C1 | 0.0487 (17) | 0.0496 (16) | 0.0249 (12) | −0.0092 (12) | 0.0025 (11) | 0.0030 (11) |
C12 | 0.0503 (19) | 0.0543 (18) | 0.0512 (19) | 0.0009 (14) | 0.0099 (15) | 0.0080 (14) |
C2 | 0.0412 (16) | 0.066 (2) | 0.0394 (15) | 0.0005 (14) | 0.0058 (12) | 0.0041 (14) |
C6 | 0.090 (3) | 0.0535 (18) | 0.0296 (14) | −0.0120 (17) | 0.0052 (16) | −0.0003 (13) |
C10 | 0.075 (2) | 0.060 (2) | 0.0441 (18) | 0.0007 (17) | 0.0277 (17) | 0.0056 (15) |
C3 | 0.0389 (17) | 0.098 (3) | 0.058 (2) | −0.0016 (17) | 0.0050 (15) | 0.017 (2) |
C11 | 0.056 (2) | 0.061 (2) | 0.067 (2) | 0.0023 (16) | 0.0296 (17) | 0.0082 (17) |
C5 | 0.101 (3) | 0.082 (3) | 0.0290 (16) | −0.046 (2) | −0.0078 (18) | 0.0032 (16) |
C4 | 0.051 (2) | 0.111 (3) | 0.051 (2) | −0.024 (2) | −0.0054 (17) | 0.020 (2) |
Geometric parameters (Å, º) top
Cu1—N1 | 2.001 (2) | C1—C6 | 1.387 (4) |
Cu1—N2 | 2.027 (2) | C1—C2 | 1.393 (5) |
Cu1—Cl1i | 2.2513 (8) | C12—C11 | 1.378 (5) |
Cu1—Cl2 | 2.2620 (9) | C12—H10 | 0.9300 |
Cu1—Cl1 | 2.6977 (9) | C2—C3 | 1.378 (4) |
Cl1—Cu1i | 2.2513 (8) | C2—H2 | 0.9300 |
N1—C7 | 1.281 (3) | C6—C5 | 1.401 (6) |
N1—O1 | 1.381 (3) | C6—H6 | 0.9300 |
N2—C12 | 1.326 (4) | C10—C11 | 1.371 (5) |
N2—C8 | 1.355 (4) | C10—H12 | 0.9300 |
C7—C1 | 1.476 (4) | C3—C4 | 1.362 (6) |
C7—C8 | 1.482 (4) | C3—H3 | 0.9300 |
O1—H1 | 0.8200 | C11—H11 | 0.9300 |
C8—C9 | 1.381 (4) | C5—C4 | 1.369 (6) |
C9—C10 | 1.378 (5) | C5—H5 | 0.9300 |
C9—H13 | 0.9300 | C4—H4 | 0.9300 |
| | | |
N1—Cu1—N2 | 78.15 (10) | C6—C1—C2 | 119.0 (3) |
N1—Cu1—Cl1i | 171.11 (8) | C6—C1—C7 | 122.1 (3) |
N2—Cu1—Cl1i | 96.46 (8) | C2—C1—C7 | 118.9 (3) |
N1—Cu1—Cl2 | 89.25 (7) | N2—C12—C11 | 123.1 (3) |
N2—Cu1—Cl2 | 164.09 (7) | N2—C12—H10 | 118.4 |
Cl1i—Cu1—Cl2 | 94.76 (3) | C11—C12—H10 | 118.4 |
N1—Cu1—Cl1 | 94.91 (8) | C3—C2—C1 | 121.0 (3) |
N2—Cu1—Cl1 | 92.62 (7) | C3—C2—H2 | 119.5 |
Cl1i—Cu1—Cl1 | 92.37 (3) | C1—C2—H2 | 119.5 |
Cl2—Cu1—Cl1 | 98.16 (3) | C1—C6—C5 | 119.3 (4) |
Cu1i—Cl1—Cu1 | 87.63 (3) | C1—C6—H6 | 120.3 |
C7—N1—O1 | 117.0 (2) | C5—C6—H6 | 120.3 |
C7—N1—Cu1 | 120.0 (2) | C11—C10—C9 | 119.0 (3) |
O1—N1—Cu1 | 122.83 (17) | C11—C10—H12 | 120.5 |
C12—N2—C8 | 118.4 (3) | C9—C10—H12 | 120.5 |
C12—N2—Cu1 | 127.0 (2) | C4—C3—C2 | 119.6 (4) |
C8—N2—Cu1 | 114.6 (2) | C4—C3—H3 | 120.2 |
N1—C7—C1 | 123.8 (3) | C2—C3—H3 | 120.2 |
N1—C7—C8 | 112.3 (2) | C10—C11—C12 | 118.7 (3) |
C1—C7—C8 | 123.8 (2) | C10—C11—H11 | 120.6 |
N1—O1—H1 | 109.5 | C12—C11—H11 | 120.6 |
N2—C8—C9 | 121.2 (3) | C4—C5—C6 | 120.1 (3) |
N2—C8—C7 | 114.9 (2) | C4—C5—H5 | 119.9 |
C9—C8—C7 | 124.0 (3) | C6—C5—H5 | 119.9 |
C10—C9—C8 | 119.6 (3) | C3—C4—C5 | 120.9 (4) |
C10—C9—H13 | 120.2 | C3—C4—H4 | 119.5 |
C8—C9—H13 | 120.2 | C5—C4—H4 | 119.5 |
Symmetry code: (i) −x, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···Cl2 | 0.82 | 2.32 | 2.954 (3) | 135 |
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