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The title compound, [Cu(C2O4)2(C6H9N2)2], crystallizes in the space group P21/c, with the Cu atom located at a centre of symmetry. It is a neutral coordination complex in which the metal exhibits a tetragonally elongated octahedral trans-CuO4N2 coordination environment. Extensive intermolecular hydrogen bonding between the oxalate anions and the ammonium cations determines the molecular packing in the crystal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803025613/rn6005sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803025613/rn6005Isup2.hkl
Contains datablock I

CCDC reference: 227750

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.035
  • wR factor = 0.091
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.605 0.880 Tmin' and Tmax expected: 0.771 0.880 RR' = 0.785 Please check that your absorption correction is appropriate. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99 PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.78 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for O3 - C2 = 5.05 su PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C2 = 1.56 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: DENZO (Otwinowski and Minor, 1997); cell refinement: DENZO and COLLECT (Hooft, 1998); data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) in WinGX (Farrugia, 1999); program(s) used to refine structure: SHELXS97 (Sheldrick, 1997) in WinGX; molecular graphics: DIAMOND (Brandenburg, 1999).

(I) top
Crystal data top
[Cu(C2O4)2(C6H9N2)2]Dx = 1.709 Mg m3
Mr = 457.89Melting point: N/A K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.5768 (4) ÅCell parameters from 4249 reflections
b = 10.6642 (3) Åθ = 2.9–27.5°
c = 7.5782 (2) ŵ = 1.28 mm1
β = 108.013 (1)°T = 120 K
V = 889.73 (5) Å3Block, pale green
Z = 20.2 × 0.1 × 0.1 mm
F(000) = 470
Data collection top
Nonius KappaCCD area-detector
diffractometer
1765 reflections with I > 2σ(I)
φ and ω scans to fill Ewald sphereRint = 0.086
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
θmax = 27.5°, θmin = 2.9°
Tmin = 0.605, Tmax = 0.880h = 1515
8409 measured reflectionsk = 1313
2023 independent reflectionsl = 99
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.035 w = 1/[σ2(Fo2) + (0.0263P)2 + 0.8605P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.091(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.47 e Å3
2023 reflectionsΔρmin = 0.56 e Å3
142 parameters
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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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. Amine H atoms were freely refined. Ammonium H atoms were fixed in calculated positions and refined in riding mode with the group allowed to rotate freely along the N2—C4 bond. Aryl H atoms were fixed in calculated positions and refined in riding mode

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
H1B0.139 (2)0.118 (3)0.348 (4)0.025 (7)*
H1A0.148 (2)0.197 (3)0.188 (4)0.021 (7)*
Cu10000.01258 (13)
O10.24205 (13)0.13669 (14)0.2149 (2)0.0157 (3)
O40.03181 (13)0.09760 (14)0.2004 (2)0.0139 (3)
O20.12189 (12)0.11570 (14)0.0367 (2)0.0136 (3)
O30.15409 (14)0.09020 (15)0.3788 (2)0.0183 (3)
N20.22712 (15)0.11713 (17)0.4045 (3)0.0137 (4)
H2A0.23890.19850.39010.021*
H2B0.15030.09750.34410.021*
H2C0.24280.10020.52460.021*
N10.15697 (16)0.12297 (18)0.2376 (3)0.0152 (4)
C50.4172 (2)0.0972 (2)0.3323 (3)0.0188 (5)
H50.43920.17530.38720.023*
C10.16504 (18)0.07888 (19)0.1619 (3)0.0123 (4)
C80.3508 (2)0.1354 (2)0.1705 (3)0.0183 (5)
H80.32950.21360.11580.022*
C40.30838 (19)0.0435 (2)0.3299 (3)0.0145 (4)
C20.11398 (18)0.0473 (2)0.2586 (3)0.0135 (4)
C60.4940 (2)0.0348 (2)0.2527 (4)0.0224 (5)
H60.56760.07040.25430.027*
C30.27242 (18)0.0743 (2)0.2512 (3)0.0140 (4)
C70.4598 (2)0.0807 (2)0.1711 (4)0.0226 (5)
H70.51030.12240.1160.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0129 (2)0.0124 (2)0.0140 (2)0.00294 (12)0.00640 (16)0.00287 (13)
O10.0149 (7)0.0144 (8)0.0196 (8)0.0023 (6)0.0080 (6)0.0000 (6)
O40.0157 (7)0.0122 (8)0.0153 (8)0.0022 (6)0.0071 (6)0.0021 (6)
O20.0142 (7)0.0122 (7)0.0156 (8)0.0013 (6)0.0063 (6)0.0021 (6)
O30.0235 (8)0.0167 (8)0.0192 (8)0.0027 (6)0.0130 (7)0.0038 (6)
N20.0137 (8)0.0116 (9)0.0154 (9)0.0004 (7)0.0039 (7)0.0005 (7)
N10.0173 (9)0.0117 (9)0.0171 (10)0.0022 (7)0.0060 (8)0.0026 (7)
C50.0175 (10)0.0151 (11)0.0231 (12)0.0025 (8)0.0053 (9)0.0006 (9)
C10.0118 (9)0.0111 (10)0.0122 (10)0.0018 (7)0.0012 (8)0.0002 (8)
C80.0219 (11)0.0120 (11)0.0215 (12)0.0028 (8)0.0075 (9)0.0005 (9)
C40.0143 (10)0.0136 (10)0.0146 (11)0.0039 (8)0.0029 (8)0.0022 (9)
C20.0131 (9)0.0120 (10)0.0134 (10)0.0010 (8)0.0012 (8)0.0027 (8)
C60.0139 (10)0.0241 (12)0.0309 (14)0.0007 (9)0.0093 (10)0.0020 (11)
C30.0143 (9)0.0134 (10)0.0134 (11)0.0006 (8)0.0028 (8)0.0034 (8)
C70.0214 (11)0.0214 (12)0.0283 (13)0.0064 (9)0.0122 (10)0.0011 (10)
Geometric parameters (Å, º) top
Cu1—O21.9579 (14)N1—H1B0.92 (3)
Cu1—O2i1.9579 (14)N1—H1A0.86 (3)
Cu1—O4i1.9675 (14)C5—C41.379 (3)
Cu1—O41.9675 (14)C5—C61.389 (3)
Cu1—N12.4980 (19)C5—H50.9300
O1—C11.248 (2)C1—C21.559 (3)
O4—C21.283 (2)C8—C71.389 (3)
O2—C11.264 (3)C8—C31.402 (3)
O3—C21.231 (3)C8—H80.9300
N2—C41.466 (3)C4—C31.398 (3)
N2—H2A0.8900C6—C71.380 (4)
N2—H2B0.8900C6—H60.9300
N2—H2C0.8900C7—H70.9300
N1—C31.407 (3)
O2—Cu1—O2i180.00 (8)C4—C5—C6120.0 (2)
O2—Cu1—O4i95.24 (6)C4—C5—H5120.0
O2i—Cu1—O4i84.76 (6)C6—C5—H5120.0
O2—Cu1—O484.76 (6)O1—C1—O2125.13 (19)
O2i—Cu1—O495.24 (6)O1—C1—C2118.71 (18)
O4i—Cu1—O4180.00 (11)O2—C1—C2116.14 (17)
O2—Cu1—N187.85 (6)C7—C8—C3120.9 (2)
O2i—Cu1—N192.15 (6)C7—C8—H8119.6
O4i—Cu1—N190.60 (6)C3—C8—H8119.6
O4—Cu1—N189.40 (6)C5—C4—C3122.0 (2)
C2—O4—Cu1112.33 (13)C5—C4—N2117.7 (2)
C1—O2—Cu1112.36 (13)C3—C4—N2120.28 (18)
C4—N2—H2A109.5O3—C2—O4126.0 (2)
C4—N2—H2B109.5O3—C2—C1119.57 (18)
H2A—N2—H2B109.5O4—C2—C1114.39 (18)
C4—N2—H2C109.5C7—C6—C5119.3 (2)
H2A—N2—H2C109.5C7—C6—H6120.3
H2B—N2—H2C109.5C5—C6—H6120.3
C3—N1—Cu1108.78 (13)C4—C3—C8117.16 (19)
C3—N1—H1B112.9 (17)C4—C3—N1120.87 (19)
Cu1—N1—H1B107.8 (17)C8—C3—N1121.7 (2)
C3—N1—H1A110.3 (17)C6—C7—C8120.7 (2)
Cu1—N1—H1A101.9 (18)C6—C7—H7119.7
H1B—N1—H1A114 (2)C8—C7—H7119.7
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O3ii0.86 (3)2.33 (3)3.181 (2)167 (2)
N2—H2A···O1iii0.891.932.799 (2)164
N2—H2A···O2iii0.892.563.184 (2)128
N2—H2B···O40.892.052.925 (2)166
N2—H2C···O1iv0.892.012.843 (2)154
N2—H2C···O3iv0.892.493.026 (2)120
N1—H1B···O3iv0.92 (3)2.05 (3)2.938 (3)162 (2)
Symmetry codes: (ii) x, y+1/2, z+1/2; (iii) x, y1/2, z+1/2; (iv) x, y, z+1.
 

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