Bis[2-(2,4-dioxopentan-3-yl­idene-κO)-1-(4-methoxy­phen­yl)hydrazinato-κN¹]copper(II)

Mol­ecules in the title compound, [Cu(C₁₂H₁₃N₂O₃)₂], are linked via weak C—H...O and C—H...π(arene) inter­actions into a three-dimensional network. The Cu atom lies on an inversion centre, and therefore the asymmetric unit contains half a formula unit. The coordination geometry about the Cu atom can be described as tetra­gonally distorted octa­hedral.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.122
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.52

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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, 2001); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1994); software used to prepare material for publication: PLATON (Spek, 2003) and Mercury (Macrae et al., 2006).

Bis[2-(2,4-dioxopentan-3-ylidene-κO)-1-(4-methoxyphenyl)hydrazinato- κN¹]copper(II)

Crystal data

[Cu(C12H13N2O3)2]	F(000) = 1100
Mr = 530.04	Dx = 1.482 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2743 reflections
a = 13.6125 (17) Å	θ = 2.3–28.0°
b = 7.5417 (9) Å	µ = 0.97 mm^−1
c = 23.135 (3) Å	T = 298 K
V = 2375.1 (5) Å^3	Block, dark red
Z = 4	0.41 × 0.26 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1979 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.040
Absorption correction: multi-scan [SADABS (Sheldrick, 1996) in SAINT (Bruker, 2000)]	θmax = 28.0°, θmin = 2.3°
Tmin = 0.678, Tmax = 0.816	h = −17→18
16264 measured reflections	k = −9→9
2743 independent reflections	l = −30→29

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0621P)^2 + 0.589P] where P = (Fo^2 + 2Fc^2)/3
2743 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.47 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.50000	0.00000	0.50000	0.0393 (1)
O1	0.42398 (10)	0.1371 (2)	0.55351 (6)	0.0428 (5)
O2	0.11896 (12)	0.2196 (3)	0.54570 (7)	0.0613 (7)
O3	0.41303 (14)	−0.0581 (3)	0.20377 (7)	0.0578 (6)
N1	0.39297 (13)	0.0336 (3)	0.44273 (8)	0.0379 (6)
N2	0.30328 (12)	0.0662 (3)	0.45540 (7)	0.0375 (6)
C1	0.27050 (16)	0.1162 (3)	0.50835 (9)	0.0360 (7)
C2	0.33182 (16)	0.1564 (3)	0.55578 (9)	0.0375 (7)
C3	0.29370 (18)	0.2281 (4)	0.61170 (10)	0.0529 (9)
C4	0.16306 (17)	0.1404 (3)	0.50789 (9)	0.0407 (7)
C5	0.10739 (17)	0.0661 (4)	0.45772 (11)	0.0493 (8)
C6	0.40179 (16)	0.0013 (3)	0.38126 (10)	0.0388 (7)
C7	0.48358 (16)	0.0595 (4)	0.35232 (10)	0.0420 (7)
C8	0.49043 (17)	0.0413 (4)	0.29254 (11)	0.0464 (8)
C9	0.41455 (18)	−0.0365 (3)	0.26242 (10)	0.0458 (8)
C10	0.33371 (18)	−0.1000 (4)	0.29172 (10)	0.0519 (9)
C11	0.32709 (17)	−0.0817 (4)	0.35071 (9)	0.0477 (8)
C12	0.4951 (2)	0.0024 (4)	0.17215 (14)	0.0642 (11)
H3A	0.34190	0.21070	0.64140	0.0790*
H3B	0.23430	0.16720	0.62200	0.0790*
H3C	0.28040	0.35250	0.60760	0.0790*
H5A	0.03960	0.10010	0.46060	0.0740*
H5B	0.11240	−0.06080	0.45800	0.0740*
H5C	0.13450	0.11140	0.42240	0.0740*
H7	0.53490	0.11140	0.37280	0.0500*
H8	0.54590	0.08160	0.27310	0.0560*
H10	0.28330	−0.15550	0.27150	0.0620*
H11	0.27240	−0.12510	0.37020	0.0570*
H12A	0.50140	0.12830	0.17680	0.0960*
H12B	0.48630	−0.02520	0.13200	0.0960*
H12C	0.55340	−0.05490	0.18620	0.0960*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0296 (2)	0.0560 (3)	0.0324 (2)	0.0046 (2)	−0.0038 (1)	−0.0073 (2)
O1	0.0315 (8)	0.0591 (10)	0.0378 (8)	0.0024 (7)	−0.0023 (6)	−0.0104 (7)
O2	0.0397 (9)	0.0913 (15)	0.0528 (10)	0.0092 (9)	0.0066 (8)	−0.0208 (10)
O3	0.0657 (12)	0.0778 (12)	0.0299 (9)	−0.0027 (10)	0.0025 (8)	−0.0024 (8)
N1	0.0308 (10)	0.0518 (11)	0.0312 (9)	0.0021 (8)	−0.0004 (8)	−0.0022 (8)
N2	0.0310 (9)	0.0470 (10)	0.0344 (10)	0.0007 (8)	0.0003 (7)	−0.0001 (8)
C1	0.0316 (11)	0.0432 (12)	0.0331 (11)	0.0023 (9)	0.0020 (8)	−0.0017 (9)
C2	0.0368 (11)	0.0400 (12)	0.0357 (11)	−0.0001 (9)	0.0043 (9)	−0.0003 (9)
C3	0.0480 (14)	0.0694 (17)	0.0414 (13)	0.0056 (12)	0.0006 (11)	−0.0162 (12)
C4	0.0341 (12)	0.0490 (13)	0.0389 (12)	0.0038 (10)	0.0022 (9)	−0.0007 (10)
C5	0.0335 (12)	0.0654 (16)	0.0490 (14)	0.0033 (11)	−0.0021 (10)	−0.0029 (13)
C6	0.0351 (11)	0.0506 (13)	0.0306 (11)	0.0054 (9)	−0.0015 (9)	−0.0020 (9)
C7	0.0389 (12)	0.0522 (13)	0.0350 (12)	−0.0030 (10)	0.0012 (9)	−0.0015 (11)
C8	0.0464 (15)	0.0564 (15)	0.0364 (13)	−0.0027 (11)	0.0054 (10)	0.0043 (11)
C9	0.0522 (14)	0.0537 (14)	0.0314 (12)	0.0058 (11)	−0.0011 (10)	−0.0020 (10)
C10	0.0435 (14)	0.0739 (18)	0.0384 (12)	−0.0053 (12)	−0.0026 (11)	−0.0105 (12)
C11	0.0371 (12)	0.0700 (17)	0.0361 (12)	−0.0061 (11)	0.0012 (10)	−0.0054 (12)
C12	0.080 (2)	0.075 (2)	0.0375 (15)	−0.0070 (15)	0.0137 (13)	0.0025 (12)

Geometric parameters (Å, º)

Cu1—O1	1.9164 (14)	C6—C11	1.388 (3)
Cu1—N1	1.9855 (18)	C7—C8	1.393 (3)
Cu1—O2^i	2.866 (2)	C8—C9	1.377 (3)
Cu1—O1^ii	1.9164 (14)	C9—C10	1.378 (3)
Cu1—N1^ii	1.9855 (18)	C10—C11	1.375 (3)
Cu1—O2^iii	2.866 (2)	C3—H3A	0.9600
O1—C2	1.264 (3)	C3—H3B	0.9600
O2—C4	1.218 (3)	C3—H3C	0.9600
O3—C9	1.367 (3)	C5—H5A	0.9600
O3—C12	1.411 (3)	C5—H5B	0.9600
N1—N2	1.279 (2)	C5—H5C	0.9600
N1—C6	1.448 (3)	C7—H7	0.9300
N2—C1	1.357 (3)	C8—H8	0.9300
C1—C2	1.412 (3)	C10—H10	0.9300
C1—C4	1.474 (3)	C11—H11	0.9300
C2—C3	1.495 (3)	C12—H12A	0.9600
C4—C5	1.495 (3)	C12—H12B	0.9600
C6—C7	1.371 (3)	C12—H12C	0.9600
Cu1···O2^i	2.866 (2)	C5···H12B^ix	2.7400
Cu1···O2^iii	2.866 (2)	C5···H5A^xii	3.0200
Cu1···H7	3.1000	C7···H12C^x	3.0800
Cu1···H5A^i	3.2000	C8···H12A	2.7600
Cu1···H7^ii	3.1000	C8···H12C	2.7000
Cu1···H5A^iii	3.2000	C9···H8^vi	3.0400
O1···N1	2.712 (2)	C11···H5C^iii	2.9000
O1···N2	2.853 (2)	C12···H8	2.5100
O1···C5^i	3.363 (3)	C12···H5C^xi	3.0100
O1···C7^ii	2.920 (3)	C12···H3A^xiii	3.0900
O1···N1^ii	2.806 (2)	H3A···C12^xiv	3.0900
O1···C6^ii	2.999 (3)	H3B···O2	2.4000
O1···O2^iii	3.208 (3)	H3B···C4	2.8200
O2···C2^iv	3.370 (3)	H3B···O3^vii	2.8800
O2···Cu1^v	2.866 (2)	H3B···H3C^iii	2.4000
O2···C3	2.827 (3)	H3C···O2	2.8100
O2···O1^iv	3.208 (3)	H3C···C2^iv	3.0000
O2···Cu1^v	2.866 (2)	H3C···C3^iv	3.0100
O3···C8^vi	3.296 (4)	H3C···H3B^iv	2.4000
O1···H7^ii	2.5900	H5A···Cu1^v	3.2000
O1···H5A^i	2.5500	H5A···O1^v	2.5500
O2···H3C	2.8100	H5A···C5^xii	3.0200
O2···H7^v	2.5500	H5A···H12B^ix	2.4500
O2···H3B	2.4000	H5A···Cu1^v	3.2000
O2···H12B^vii	2.8600	H5B···N2	2.7700
O3···H3B^viii	2.8800	H5C···N2	2.4400
O3···H8^vi	2.8300	H5C···C12^ix	3.0100
N1···O1	2.712 (2)	H5C···H12B^ix	2.5900
N1···C2	2.897 (3)	H5C···C11^iv	2.9000
N1···O1^ii	2.806 (2)	H7···Cu1	3.1000
N1···C4^iii	3.413 (3)	H7···O2^i	2.5500
N2···O1	2.853 (2)	H7···O1^ii	2.5900
N2···H5B	2.7700	H8···C12	2.5100
N2···H5C	2.4400	H8···H12A	2.3400
N2···H11	2.4800	H8···H12C	2.2600
C3···O2	2.827 (3)	H8···O3^x	2.8300
C5···C12^ix	3.405 (4)	H8···C9^x	3.0400
C5···O1^v	3.363 (3)	H11···N2	2.4800
C7···C12^x	3.400 (4)	H12A···C8	2.7600
C7···O1^ii	2.920 (3)	H12A···H8	2.3400
C8···C12^x	3.578 (4)	H12B···O2^viii	2.8600
C8···O3^x	3.296 (4)	H12B···C5^xi	2.7400
C12···C5^xi	3.405 (4)	H12B···H5A^xi	2.4500
C12···C8^vi	3.578 (4)	H12B···H5C^xi	2.5900
C12···C7^vi	3.400 (4)	H12C···C8	2.7000
C2···H3C^iii	3.0000	H12C···H8	2.2600
C3···H3C^iii	3.0100	H12C···C7^vi	3.0800
C4···H3B	2.8200
O1—Cu1—N1	88.05 (7)	C6—C7—C8	120.5 (2)
O1—Cu1—O2^i	98.36 (6)	C7—C8—C9	119.6 (2)
O1—Cu1—O1^ii	180.00	O3—C9—C8	124.4 (2)
O1—Cu1—N1^ii	91.95 (7)	O3—C9—C10	115.8 (2)
O1—Cu1—O2^iii	81.64 (6)	C8—C9—C10	119.9 (2)
O2^i—Cu1—N1	94.26 (7)	C9—C10—C11	120.4 (2)
O1^ii—Cu1—N1	91.95 (7)	C6—C11—C10	120.2 (2)
N1—Cu1—N1^ii	180.00	C2—C3—H3A	109.00
O2^iii—Cu1—N1	85.74 (7)	C2—C3—H3B	110.00
O1^ii—Cu1—O2^i	81.64 (6)	C2—C3—H3C	109.00
O2^i—Cu1—N1^ii	85.74 (7)	H3A—C3—H3B	109.00
O2^i—Cu1—O2^iii	180.00	H3A—C3—H3C	109.00
O1^ii—Cu1—N1^ii	88.05 (7)	H3B—C3—H3C	109.00
O1^ii—Cu1—O2^iii	98.36 (6)	C4—C5—H5A	109.00
O2^iii—Cu1—N1^ii	94.26 (7)	C4—C5—H5B	109.00
Cu1—O1—C2	128.68 (14)	C4—C5—H5C	109.00
Cu1^v—O2—C4	112.06 (14)	H5A—C5—H5B	110.00
C9—O3—C12	117.7 (2)	H5A—C5—H5C	109.00
Cu1—N1—N2	124.88 (14)	H5B—C5—H5C	109.00
Cu1—N1—C6	124.97 (14)	C6—C7—H7	120.00
N2—N1—C6	109.66 (17)	C8—C7—H7	120.00
N1—N2—C1	125.02 (18)	C7—C8—H8	120.00
N2—C1—C2	124.53 (19)	C9—C8—H8	120.00
N2—C1—C4	110.74 (18)	C9—C10—H10	120.00
C2—C1—C4	124.46 (19)	C11—C10—H10	120.00
O1—C2—C1	122.00 (19)	C6—C11—H11	120.00
O1—C2—C3	114.97 (19)	C10—C11—H11	120.00
C1—C2—C3	123.0 (2)	O3—C12—H12A	109.00
O2—C4—C1	123.0 (2)	O3—C12—H12B	109.00
O2—C4—C5	119.5 (2)	O3—C12—H12C	109.00
C1—C4—C5	117.53 (19)	H12A—C12—H12B	110.00
N1—C6—C7	119.5 (2)	H12A—C12—H12C	109.00
N1—C6—C11	121.03 (19)	H12B—C12—H12C	109.00
C7—C6—C11	119.4 (2)
N1—Cu1—O1—C2	27.20 (18)	N2—N1—C6—C7	143.6 (2)
O2^i—Cu1—O1—C2	121.22 (18)	N2—N1—C6—C11	−34.0 (3)
N1^ii—Cu1—O1—C2	−152.80 (18)	N1—N2—C1—C4	−179.2 (2)
O2^iii—Cu1—O1—C2	−58.78 (18)	N1—N2—C1—C2	6.5 (4)
O1—Cu1—N1—N2	−24.3 (2)	N2—C1—C2—O1	−4.9 (4)
O1—Cu1—N1—C6	164.60 (19)	N2—C1—C2—C3	173.8 (2)
O2^i—Cu1—N1—N2	−122.5 (2)	C4—C1—C2—O1	−178.3 (2)
O2^i—Cu1—N1—C6	66.36 (19)	C2—C1—C4—O2	10.2 (4)
O1^ii—Cu1—N1—N2	155.7 (2)	C2—C1—C4—C5	−171.0 (2)
O1^ii—Cu1—N1—C6	−15.40 (19)	C4—C1—C2—C3	0.4 (4)
O2^iii—Cu1—N1—N2	57.5 (2)	N2—C1—C4—O2	−164.0 (2)
O2^iii—Cu1—N1—C6	−113.64 (19)	N2—C1—C4—C5	14.8 (3)
Cu1—O1—C2—C1	−18.0 (3)	N1—C6—C7—C8	−175.3 (2)
Cu1—O1—C2—C3	163.26 (16)	C11—C6—C7—C8	2.2 (4)
Cu1^v—O2—C4—C1	125.40 (19)	N1—C6—C11—C10	175.4 (2)
Cu1^v—O2—C4—C5	−53.4 (3)	C7—C6—C11—C10	−2.1 (4)
C12—O3—C9—C8	0.5 (4)	C6—C7—C8—C9	−0.3 (4)
C12—O3—C9—C10	−179.0 (2)	C7—C8—C9—C10	−1.8 (4)
Cu1—N1—N2—C1	13.3 (4)	C7—C8—C9—O3	178.8 (2)
C6—N1—N2—C1	−174.4 (2)	O3—C9—C10—C11	−178.7 (2)
Cu1—N1—C6—C7	−44.1 (3)	C8—C9—C10—C11	1.8 (4)
Cu1—N1—C6—C11	138.3 (2)	C9—C10—C11—C6	0.1 (4)

Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+1, −y, −z+1; (iii) −x+1/2, y−1/2, z; (iv) −x+1/2, y+1/2, z; (v) x−1/2, −y+1/2, −z+1; (vi) −x+1, y−1/2, −z+1/2; (vii) −x+1/2, −y, z+1/2; (viii) −x+1/2, −y, z−1/2; (ix) x−1/2, y, −z+1/2; (x) −x+1, y+1/2, −z+1/2; (xi) x+1/2, y, −z+1/2; (xii) −x, −y, −z+1; (xiii) x, −y+1/2, z−1/2; (xiv) x, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···O2	0.96	2.40	2.827 (3)	107
C7—H7···O2^i	0.93	2.55	3.426 (3)	158
C5—H5A···O1^v	0.96	2.55	3.363 (3)	142
C7—H7···O1^ii	0.93	2.59	2.920 (3)	101
C12—H12A···Cg^x	0.96	2.93	3.841 (3)	160

Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+1, −y, −z+1; (v) x−1/2, −y+1/2, −z+1; (x) −x+1, y+1/2, −z+1/2.