μ-Oxalato-1κ²O,O′:2κ²O′′,O′′′-bis­(chloro{[1-(2-pyridyl-κN)ethyl­idene]hydrazine-κN}copper(II))

The title compound, [Cu₂(C₂O₄)Cl₂(C₇H₉N₃)₂], contains neutral mol­ecules of a centrosymmetric dinuclear oxalate-bridged copper(II) complex, in which the oxalate ligand is coordinated in a bis-bidentate bridging mode to the Cu atoms. Each Cu atom has a distorted square-pyramidal environment, being coordinated by two N atoms of the [1-(pyridin-2-yl)­ethyl­idene]hydrazine ligand, two O atoms of the doubly deprotonated oxalate anion and one Cl⁻ anion.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.037
• wR factor = 0.099
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT369_ALERT_2_B Long   C(sp2)-C(sp2) Bond  C1     -   C1_a   ...       1.57 Ang.

Alert level C
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.11 Ratio

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: KM4 CCD Software (Kuma Diffraction, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Dichloro(µ₄-oxalato-1κ²O,O':2κ²O'',O''')bis{[1-(pyridin-2- yl)ethylidene]hydrazine-κ²N,N'}dicopper(II)

Crystal data

[Cu2(C2O4)(C7H9N3)2Cl2]	F(000) = 560
Mr = 556.34	Dx = 1.936 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2479 reflections
a = 9.3785 (6) Å	θ = 1.0–27.5°
b = 9.2002 (6) Å	µ = 2.55 mm^−1
c = 11.2501 (8) Å	T = 100 K
β = 100.422 (6)°	Block, blue
V = 954.6 (1) Å^3	0.23 × 0.17 × 0.11 mm
Z = 2

Data collection

Nonius KappaCCD area-detector diffractometer	2241 independent reflections
Radiation source: fine-focus sealed tube	1988 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	Rint = 0.074
Detector resolution: 9 pixels mm^-1	θmax = 28.4°, θmin = 3.4°
φ scans, and ω scans with κ offset	h = −12→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −11→12
Tmin = 0.597, Tmax = 0.757	l = −14→13
6391 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0537P)^2 + 0.2578P] where P = (Fo^2 + 2Fc^2)/3
2241 reflections	(Δ/σ)max = 0.001
143 parameters	Δρmax = 0.79 e Å^−3
0 restraints	Δρmin = −1.09 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Cu1	0.00756 (3)	0.05846 (3)	0.76381 (3)	0.01037 (13)
Cl1	−0.00503 (6)	0.30320 (7)	0.75701 (6)	0.01424 (16)
O1	−0.13434 (19)	0.04552 (19)	0.87453 (16)	0.0115 (4)
O2	−0.15505 (18)	0.0031 (2)	1.06588 (16)	0.0139 (4)
N1	0.1431 (2)	0.0367 (2)	0.64771 (19)	0.0108 (4)
N2	−0.0413 (2)	−0.1461 (2)	0.7057 (2)	0.0116 (4)
N3	−0.1401 (3)	−0.2322 (3)	0.7504 (2)	0.0142 (5)
H1N	−0.211 (4)	−0.175 (3)	0.769 (3)	0.021*
H2N	−0.179 (4)	−0.302 (3)	0.701 (3)	0.021*
C1	−0.0837 (3)	0.0135 (3)	0.9838 (2)	0.0109 (5)
C2	0.1378 (3)	−0.0953 (3)	0.5932 (2)	0.0108 (5)
C3	0.2205 (3)	−0.1261 (3)	0.5059 (2)	0.0127 (5)
H3	0.2152	−0.2168	0.4688	0.015*
C4	0.3115 (3)	−0.0191 (3)	0.4748 (2)	0.0146 (5)
H4	0.3671	−0.0371	0.4158	0.018*
C5	0.3188 (3)	0.1144 (3)	0.5320 (2)	0.0146 (5)
H5	0.3807	0.1865	0.5132	0.018*
C6	0.2325 (3)	0.1391 (3)	0.6178 (2)	0.0127 (5)
H6	0.2366	0.2292	0.6558	0.015*
C7	0.0348 (3)	−0.1999 (3)	0.6317 (2)	0.0103 (5)
C8	0.0198 (3)	−0.3526 (3)	0.5869 (3)	0.0160 (5)
H8A	0.0307	−0.4180	0.6544	0.024*
H8B	0.0933	−0.3725	0.5398	0.024*
H8C	−0.0742	−0.3656	0.5377	0.024*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.01086 (19)	0.0094 (2)	0.0111 (2)	0.00006 (11)	0.00253 (12)	−0.00014 (11)
Cl1	0.0164 (3)	0.0095 (3)	0.0171 (3)	−0.0004 (2)	0.0039 (2)	−0.0012 (2)
O1	0.0114 (9)	0.0130 (9)	0.0099 (9)	0.0014 (7)	0.0009 (7)	0.0018 (7)
O2	0.0120 (9)	0.0171 (10)	0.0127 (9)	0.0004 (7)	0.0026 (7)	0.0009 (7)
N1	0.0107 (10)	0.0111 (10)	0.0096 (10)	−0.0004 (8)	−0.0004 (8)	0.0006 (8)
N2	0.0117 (10)	0.0109 (10)	0.0118 (11)	−0.0017 (8)	0.0010 (8)	0.0014 (8)
N3	0.0141 (11)	0.0128 (12)	0.0165 (12)	−0.0039 (9)	0.0049 (9)	−0.0005 (9)
C1	0.0125 (12)	0.0060 (12)	0.0139 (12)	−0.0012 (9)	0.0015 (9)	−0.0011 (9)
C2	0.0096 (11)	0.0103 (12)	0.0105 (12)	0.0018 (9)	−0.0038 (9)	0.0011 (9)
C3	0.0123 (12)	0.0114 (13)	0.0134 (12)	0.0015 (9)	−0.0004 (9)	−0.0009 (9)
C4	0.0113 (12)	0.0205 (14)	0.0122 (12)	0.0014 (10)	0.0025 (9)	0.0028 (10)
C5	0.0123 (12)	0.0137 (13)	0.0176 (13)	−0.0007 (10)	0.0017 (10)	0.0025 (10)
C6	0.0131 (12)	0.0109 (12)	0.0131 (13)	−0.0014 (10)	−0.0003 (9)	−0.0008 (9)
C7	0.0095 (12)	0.0094 (12)	0.0110 (12)	0.0007 (9)	−0.0008 (9)	0.0004 (9)
C8	0.0183 (13)	0.0096 (12)	0.0205 (14)	−0.0007 (10)	0.0045 (10)	−0.0012 (10)

Geometric parameters (Å, º)

Cu1—O1	1.9839 (18)	C1—C1^i	1.565 (5)
Cu1—N1	1.991 (2)	C2—C3	1.387 (4)
Cu1—N2	2.018 (2)	C2—C7	1.482 (3)
Cu1—O2^i	2.2240 (19)	C3—C4	1.388 (4)
Cu1—Cl1	2.2553 (9)	C3—H3	0.9300
Cu1—Cu1^i	5.4489 (11)	C4—C5	1.383 (4)
O1—C1	1.270 (3)	C4—H4	0.9300
O2—C1	1.239 (3)	C5—C6	1.386 (4)
O2—Cu1^i	2.2240 (19)	C5—H5	0.9300
N1—C6	1.344 (3)	C6—H6	0.9300
N1—C2	1.357 (3)	C7—C8	1.490 (3)
N2—C7	1.290 (3)	C8—H8A	0.9600
N2—N3	1.381 (3)	C8—H8B	0.9600
N3—H1N	0.90 (3)	C8—H8C	0.9600
N3—H2N	0.88 (3)
O1—Cu1—N1	170.51 (8)	O2—C1—C1^i	117.9 (3)
O1—Cu1—N2	90.49 (8)	O1—C1—C1^i	116.5 (3)
N1—Cu1—N2	80.10 (9)	N1—C2—C3	121.6 (2)
O1—Cu1—O2^i	80.05 (7)	N1—C2—C7	114.9 (2)
N1—Cu1—O2^i	99.68 (8)	C3—C2—C7	123.5 (2)
N2—Cu1—O2^i	96.37 (8)	C2—C3—C4	118.8 (2)
O1—Cu1—Cl1	92.54 (5)	C2—C3—H3	120.6
N1—Cu1—Cl1	96.55 (6)	C4—C3—H3	120.6
N2—Cu1—Cl1	155.90 (7)	C5—C4—C3	119.6 (2)
O2^i—Cu1—Cl1	107.70 (5)	C5—C4—H4	120.2
O1—Cu1—Cu1^i	40.28 (5)	C3—C4—H4	120.2
N1—Cu1—Cu1^i	138.80 (6)	C4—C5—C6	118.9 (2)
N2—Cu1—Cu1^i	95.01 (6)	C4—C5—H5	120.5
O2^i—Cu1—Cu1^i	39.77 (5)	C6—C5—H5	120.5
Cl1—Cu1—Cu1^i	102.695 (19)	N1—C6—C5	121.9 (2)
C1—O1—Cu1	116.45 (16)	N1—C6—H6	119.0
C1—O2—Cu1^i	109.03 (15)	C5—C6—H6	119.0
C6—N1—C2	119.2 (2)	N2—C7—C2	113.9 (2)
C6—N1—Cu1	126.50 (18)	N2—C7—C8	123.4 (2)
C2—N1—Cu1	114.27 (17)	C2—C7—C8	122.7 (2)
C7—N2—N3	120.1 (2)	C7—C8—H8A	109.5
C7—N2—Cu1	116.55 (17)	C7—C8—H8B	109.5
N3—N2—Cu1	123.04 (17)	H8A—C8—H8B	109.5
N2—N3—H1N	109 (2)	C7—C8—H8C	109.5
N2—N3—H2N	114 (2)	H8A—C8—H8C	109.5
H1N—N3—H2N	109 (3)	H8B—C8—H8C	109.5
O2—C1—O1	125.6 (2)
N2—Cu1—O1—C1	97.47 (18)	Cu1^i—O2—C1—C1^i	−1.4 (3)
O2^i—Cu1—O1—C1	1.09 (17)	Cu1—O1—C1—O2	178.6 (2)
Cl1—Cu1—O1—C1	−106.45 (17)	Cu1—O1—C1—C1^i	−0.7 (3)
Cu1^i—Cu1—O1—C1	0.29 (14)	C6—N1—C2—C3	−1.2 (4)
N2—Cu1—N1—C6	176.9 (2)	Cu1—N1—C2—C3	177.04 (19)
O2^i—Cu1—N1—C6	−88.2 (2)	C6—N1—C2—C7	−179.4 (2)
Cl1—Cu1—N1—C6	21.1 (2)	Cu1—N1—C2—C7	−1.2 (3)
Cu1^i—Cu1—N1—C6	−96.8 (2)	N1—C2—C3—C4	0.6 (4)
N2—Cu1—N1—C2	−1.14 (17)	C7—C2—C3—C4	178.6 (2)
O2^i—Cu1—N1—C2	93.71 (17)	C2—C3—C4—C5	0.7 (4)
Cl1—Cu1—N1—C2	−157.01 (16)	C3—C4—C5—C6	−1.3 (4)
Cu1^i—Cu1—N1—C2	85.16 (19)	C2—N1—C6—C5	0.6 (4)
O1—Cu1—N2—C7	−175.09 (19)	Cu1—N1—C6—C5	−177.41 (19)
N1—Cu1—N2—C7	3.71 (19)	C4—C5—C6—N1	0.6 (4)
O2^i—Cu1—N2—C7	−95.05 (19)	N3—N2—C7—C2	−179.0 (2)
Cl1—Cu1—N2—C7	87.6 (2)	Cu1—N2—C7—C2	−5.3 (3)
Cu1^i—Cu1—N2—C7	−135.00 (18)	N3—N2—C7—C8	1.9 (4)
O1—Cu1—N2—N3	−1.6 (2)	Cu1—N2—C7—C8	175.59 (19)
N1—Cu1—N2—N3	177.2 (2)	N1—C2—C7—N2	4.3 (3)
O2^i—Cu1—N2—N3	78.5 (2)	C3—C2—C7—N2	−173.9 (2)
Cl1—Cu1—N2—N3	−98.9 (2)	N1—C2—C7—C8	−176.6 (2)
Cu1^i—Cu1—N2—N3	38.5 (2)	C3—C2—C7—C8	5.2 (4)
Cu1^i—O2—C1—O1	179.3 (2)

Symmetry code: (i) −x, −y, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N···Cl1^ii	0.90 (3)	2.63 (3)	3.330 (2)	135 (3)
N3—H2N···O1^ii	0.88 (3)	2.29 (3)	3.091 (3)	152 (3)

Symmetry code: (ii) −x−1/2, y−1/2, −z+3/2.