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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807000098/sa2033sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807000098/sa2033Isup2.hkl
Contains datablock I

CCDC reference: 636793

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

Computing details top

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) top
Crystal data top
[Cu2(C2O4)(C7H9N3)2Cl2]F(000) = 560
Mr = 556.34Dx = 1.936 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2479 reflections
a = 9.3785 (6) Åθ = 1.0–27.5°
b = 9.2002 (6) ŵ = 2.55 mm1
c = 11.2501 (8) ÅT = 100 K
β = 100.422 (6)°Block, blue
V = 954.6 (1) Å30.23 × 0.17 × 0.11 mm
Z = 2
Data collection top
Nonius KappaCCD area-detector
diffractometer
2241 independent reflections
Radiation source: fine-focus sealed tube1988 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromatorRint = 0.074
Detector resolution: 9 pixels mm-1θmax = 28.4°, θmin = 3.4°
φ scans, and ω scans with κ offseth = 1211
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1112
Tmin = 0.597, Tmax = 0.757l = 1413
6391 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0537P)2 + 0.2578P]
where P = (Fo2 + 2Fc2)/3
2241 reflections(Δ/σ)max = 0.001
143 parametersΔρmax = 0.79 e Å3
0 restraintsΔρmin = 1.09 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Cu10.00756 (3)0.05846 (3)0.76381 (3)0.01037 (13)
Cl10.00503 (6)0.30320 (7)0.75701 (6)0.01424 (16)
O10.13434 (19)0.04552 (19)0.87453 (16)0.0115 (4)
O20.15505 (18)0.0031 (2)1.06588 (16)0.0139 (4)
N10.1431 (2)0.0367 (2)0.64771 (19)0.0108 (4)
N20.0413 (2)0.1461 (2)0.7057 (2)0.0116 (4)
N30.1401 (3)0.2322 (3)0.7504 (2)0.0142 (5)
H1N0.211 (4)0.175 (3)0.769 (3)0.021*
H2N0.179 (4)0.302 (3)0.701 (3)0.021*
C10.0837 (3)0.0135 (3)0.9838 (2)0.0109 (5)
C20.1378 (3)0.0953 (3)0.5932 (2)0.0108 (5)
C30.2205 (3)0.1261 (3)0.5059 (2)0.0127 (5)
H30.21520.21680.46880.015*
C40.3115 (3)0.0191 (3)0.4748 (2)0.0146 (5)
H40.36710.03710.41580.018*
C50.3188 (3)0.1144 (3)0.5320 (2)0.0146 (5)
H50.38070.18650.51320.018*
C60.2325 (3)0.1391 (3)0.6178 (2)0.0127 (5)
H60.23660.22920.65580.015*
C70.0348 (3)0.1999 (3)0.6317 (2)0.0103 (5)
C80.0198 (3)0.3526 (3)0.5869 (3)0.0160 (5)
H8A0.03070.41800.65440.024*
H8B0.09330.37250.53980.024*
H8C0.07420.36560.53770.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.01086 (19)0.0094 (2)0.0111 (2)0.00006 (11)0.00253 (12)0.00014 (11)
Cl10.0164 (3)0.0095 (3)0.0171 (3)0.0004 (2)0.0039 (2)0.0012 (2)
O10.0114 (9)0.0130 (9)0.0099 (9)0.0014 (7)0.0009 (7)0.0018 (7)
O20.0120 (9)0.0171 (10)0.0127 (9)0.0004 (7)0.0026 (7)0.0009 (7)
N10.0107 (10)0.0111 (10)0.0096 (10)0.0004 (8)0.0004 (8)0.0006 (8)
N20.0117 (10)0.0109 (10)0.0118 (11)0.0017 (8)0.0010 (8)0.0014 (8)
N30.0141 (11)0.0128 (12)0.0165 (12)0.0039 (9)0.0049 (9)0.0005 (9)
C10.0125 (12)0.0060 (12)0.0139 (12)0.0012 (9)0.0015 (9)0.0011 (9)
C20.0096 (11)0.0103 (12)0.0105 (12)0.0018 (9)0.0038 (9)0.0011 (9)
C30.0123 (12)0.0114 (13)0.0134 (12)0.0015 (9)0.0004 (9)0.0009 (9)
C40.0113 (12)0.0205 (14)0.0122 (12)0.0014 (10)0.0025 (9)0.0028 (10)
C50.0123 (12)0.0137 (13)0.0176 (13)0.0007 (10)0.0017 (10)0.0025 (10)
C60.0131 (12)0.0109 (12)0.0131 (13)0.0014 (10)0.0003 (9)0.0008 (9)
C70.0095 (12)0.0094 (12)0.0110 (12)0.0007 (9)0.0008 (9)0.0004 (9)
C80.0183 (13)0.0096 (12)0.0205 (14)0.0007 (10)0.0045 (10)0.0012 (10)
Geometric parameters (Å, º) top
Cu1—O11.9839 (18)C1—C1i1.565 (5)
Cu1—N11.991 (2)C2—C31.387 (4)
Cu1—N22.018 (2)C2—C71.482 (3)
Cu1—O2i2.2240 (19)C3—C41.388 (4)
Cu1—Cl12.2553 (9)C3—H30.9300
Cu1—Cu1i5.4489 (11)C4—C51.383 (4)
O1—C11.270 (3)C4—H40.9300
O2—C11.239 (3)C5—C61.386 (4)
O2—Cu1i2.2240 (19)C5—H50.9300
N1—C61.344 (3)C6—H60.9300
N1—C21.357 (3)C7—C81.490 (3)
N2—C71.290 (3)C8—H8A0.9600
N2—N31.381 (3)C8—H8B0.9600
N3—H1N0.90 (3)C8—H8C0.9600
N3—H2N0.88 (3)
O1—Cu1—N1170.51 (8)O2—C1—C1i117.9 (3)
O1—Cu1—N290.49 (8)O1—C1—C1i116.5 (3)
N1—Cu1—N280.10 (9)N1—C2—C3121.6 (2)
O1—Cu1—O2i80.05 (7)N1—C2—C7114.9 (2)
N1—Cu1—O2i99.68 (8)C3—C2—C7123.5 (2)
N2—Cu1—O2i96.37 (8)C2—C3—C4118.8 (2)
O1—Cu1—Cl192.54 (5)C2—C3—H3120.6
N1—Cu1—Cl196.55 (6)C4—C3—H3120.6
N2—Cu1—Cl1155.90 (7)C5—C4—C3119.6 (2)
O2i—Cu1—Cl1107.70 (5)C5—C4—H4120.2
O1—Cu1—Cu1i40.28 (5)C3—C4—H4120.2
N1—Cu1—Cu1i138.80 (6)C4—C5—C6118.9 (2)
N2—Cu1—Cu1i95.01 (6)C4—C5—H5120.5
O2i—Cu1—Cu1i39.77 (5)C6—C5—H5120.5
Cl1—Cu1—Cu1i102.695 (19)N1—C6—C5121.9 (2)
C1—O1—Cu1116.45 (16)N1—C6—H6119.0
C1—O2—Cu1i109.03 (15)C5—C6—H6119.0
C6—N1—C2119.2 (2)N2—C7—C2113.9 (2)
C6—N1—Cu1126.50 (18)N2—C7—C8123.4 (2)
C2—N1—Cu1114.27 (17)C2—C7—C8122.7 (2)
C7—N2—N3120.1 (2)C7—C8—H8A109.5
C7—N2—Cu1116.55 (17)C7—C8—H8B109.5
N3—N2—Cu1123.04 (17)H8A—C8—H8B109.5
N2—N3—H1N109 (2)C7—C8—H8C109.5
N2—N3—H2N114 (2)H8A—C8—H8C109.5
H1N—N3—H2N109 (3)H8B—C8—H8C109.5
O2—C1—O1125.6 (2)
N2—Cu1—O1—C197.47 (18)Cu1i—O2—C1—C1i1.4 (3)
O2i—Cu1—O1—C11.09 (17)Cu1—O1—C1—O2178.6 (2)
Cl1—Cu1—O1—C1106.45 (17)Cu1—O1—C1—C1i0.7 (3)
Cu1i—Cu1—O1—C10.29 (14)C6—N1—C2—C31.2 (4)
N2—Cu1—N1—C6176.9 (2)Cu1—N1—C2—C3177.04 (19)
O2i—Cu1—N1—C688.2 (2)C6—N1—C2—C7179.4 (2)
Cl1—Cu1—N1—C621.1 (2)Cu1—N1—C2—C71.2 (3)
Cu1i—Cu1—N1—C696.8 (2)N1—C2—C3—C40.6 (4)
N2—Cu1—N1—C21.14 (17)C7—C2—C3—C4178.6 (2)
O2i—Cu1—N1—C293.71 (17)C2—C3—C4—C50.7 (4)
Cl1—Cu1—N1—C2157.01 (16)C3—C4—C5—C61.3 (4)
Cu1i—Cu1—N1—C285.16 (19)C2—N1—C6—C50.6 (4)
O1—Cu1—N2—C7175.09 (19)Cu1—N1—C6—C5177.41 (19)
N1—Cu1—N2—C73.71 (19)C4—C5—C6—N10.6 (4)
O2i—Cu1—N2—C795.05 (19)N3—N2—C7—C2179.0 (2)
Cl1—Cu1—N2—C787.6 (2)Cu1—N2—C7—C25.3 (3)
Cu1i—Cu1—N2—C7135.00 (18)N3—N2—C7—C81.9 (4)
O1—Cu1—N2—N31.6 (2)Cu1—N2—C7—C8175.59 (19)
N1—Cu1—N2—N3177.2 (2)N1—C2—C7—N24.3 (3)
O2i—Cu1—N2—N378.5 (2)C3—C2—C7—N2173.9 (2)
Cl1—Cu1—N2—N398.9 (2)N1—C2—C7—C8176.6 (2)
Cu1i—Cu1—N2—N338.5 (2)C3—C2—C7—C85.2 (4)
Cu1i—O2—C1—O1179.3 (2)
Symmetry code: (i) x, y, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H1N···Cl1ii0.90 (3)2.63 (3)3.330 (2)135 (3)
N3—H2N···O1ii0.88 (3)2.29 (3)3.091 (3)152 (3)
Symmetry code: (ii) x1/2, y1/2, z+3/2.
 

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