Di-μ-chloro-bis­[chloro­(phenyl 2-pyridyl ketone oxime-κ²N,N′)copper(II)]

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 Cu^II 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.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](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

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Computing details

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)]

Crystal data

[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) Å^3	0.32 × 0.26 × 0.20 mm
Z = 2

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0569P)^2 + 0.7387P] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Cu1—N1	2.001 (2)	C1—C6	1.387 (4)
Cu1—N2	2.027 (2)	C1—C2	1.393 (5)
Cu1—Cl1^i	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—Cu1^i	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—Cl1^i	171.11 (8)	C6—C1—C7	122.1 (3)
N2—Cu1—Cl1^i	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
Cl1^i—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
Cl1^i—Cu1—Cl1	92.37 (3)	C1—C2—H2	119.5
Cl2—Cu1—Cl1	98.16 (3)	C1—C6—C5	119.3 (4)
Cu1^i—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)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl2	0.82	2.32	2.954 (3)	135