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The title compound, [Cu2(C8H16N4O2)(C10H8N2)2](NO3)2, contains a centrosymmetric binuclear copper(II) complex bridged by a deprotonated oxamide ligand. The Cu atoms have a distorted square-pyramidal coordination geometry, with one of the 2,2′-bipyridine N atoms at the apex. The copper complex cations assemble in chains along the c axis via π–π overlaps of bipyridine ligands of neighbouring complexes. These chains are connected in the crystal structure via N—H...O and C—H...O hydrogen bonds with the nitrate ions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045351/ez2047sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045351/ez2047Isup2.hkl
Contains datablock I

CCDC reference: 629656

Key indicators

  • Single-crystal X-ray study
  • T = 203 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.026
  • wR factor = 0.072
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N5 PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A .. O2 .. 2.63 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H3B .. O4 .. 2.68 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H8A .. O3 .. 2.65 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 N O3
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 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 0 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 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

[µ-N,N'-Bis(3-aminopropyl)oxamidato(2-)]bis[(2,2'-bipyridine)copper(II)] dinitrate top
Crystal data top
[Cu2(C8H16N4O2)(C10H8N2)2](NO3)2Z = 1
Mr = 763.72F(000) = 392
Triclinic, P1Dx = 1.648 Mg m3
a = 8.9069 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.3003 (4) ÅCell parameters from 6676 reflections
c = 10.3457 (4) Åθ = 2.2–27.5°
α = 103.290 (1)°µ = 1.45 mm1
β = 107.605 (1)°T = 203 K
γ = 112.436 (1)°Prism, green
V = 769.31 (5) Å30.20 × 0.18 × 0.15 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
3353 independent reflections
Radiation source: fine-focus sealed tube3123 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.760, Tmax = 0.812k = 1313
7305 measured reflectionsl = 1313
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)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0412P)2 + 0.358P]
where P = (Fo2 + 2Fc2)/3
3353 reflections(Δ/σ)max < 0.001
217 parametersΔρmax = 0.62 e Å3
0 restraintsΔρmin = 0.50 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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu0.10320 (3)0.40253 (2)0.20585 (2)0.01786 (8)
N10.2431 (2)0.53032 (17)0.42419 (15)0.0232 (3)
H1A0.17440.56560.45330.028*
H1D0.25550.46730.47050.028*
N20.20273 (19)0.57748 (16)0.15575 (15)0.0191 (3)
N30.01608 (19)0.21416 (16)0.24350 (15)0.0187 (3)
N40.2446 (2)0.27415 (17)0.15503 (16)0.0216 (3)
N50.1802 (2)0.60015 (18)0.30460 (19)0.0301 (3)
O10.11293 (16)0.67549 (13)0.01459 (13)0.0214 (2)
O20.1022 (2)0.5290 (2)0.3461 (2)0.0470 (4)
O30.1975 (4)0.6196 (3)0.1884 (2)0.0735 (7)
O40.2512 (2)0.64577 (19)0.37818 (18)0.0392 (4)
C10.4234 (3)0.6621 (2)0.4793 (2)0.0311 (4)
H1B0.50510.62530.46240.037*
H1C0.47040.71600.58590.037*
C20.4207 (3)0.7728 (2)0.4049 (2)0.0306 (4)
H2A0.53780.86630.45800.037*
H2B0.32910.80040.41280.037*
C30.3817 (2)0.7111 (2)0.24318 (19)0.0242 (4)
H3A0.38950.79090.20490.029*
H3B0.47270.68330.23400.029*
C40.0898 (2)0.57342 (17)0.03905 (17)0.0172 (3)
C50.1415 (2)0.1950 (2)0.2941 (2)0.0243 (3)
H5A0.18070.26790.30560.029*
C60.2153 (3)0.0716 (2)0.3301 (2)0.0301 (4)
H6A0.30260.06100.36600.036*
C70.1584 (3)0.0357 (2)0.3123 (2)0.0319 (4)
H7A0.20650.12050.33610.038*
C80.0300 (3)0.0171 (2)0.2591 (2)0.0283 (4)
H8A0.00960.08960.24570.034*
C90.0402 (2)0.10982 (18)0.22559 (18)0.0195 (3)
C100.1805 (2)0.14022 (19)0.17008 (18)0.0199 (3)
C110.2427 (3)0.0377 (2)0.1363 (2)0.0270 (4)
H11A0.19260.05750.14340.032*
C120.3800 (3)0.0791 (2)0.0922 (2)0.0330 (4)
H12A0.42570.01260.07030.040*
C130.4497 (3)0.2185 (3)0.0803 (2)0.0329 (4)
H13A0.54470.24910.05250.039*
C140.3762 (3)0.3119 (2)0.1102 (2)0.0274 (4)
H14A0.42000.40510.09880.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.01958 (12)0.01440 (11)0.01725 (11)0.00600 (8)0.00574 (8)0.00937 (8)
N10.0254 (7)0.0218 (7)0.0191 (6)0.0081 (6)0.0091 (6)0.0092 (6)
N20.0175 (6)0.0158 (6)0.0192 (6)0.0045 (5)0.0052 (5)0.0093 (5)
N30.0196 (7)0.0160 (6)0.0192 (6)0.0075 (5)0.0069 (5)0.0091 (5)
N40.0222 (7)0.0203 (7)0.0231 (7)0.0103 (6)0.0098 (6)0.0097 (6)
N50.0399 (9)0.0243 (8)0.0366 (9)0.0177 (7)0.0218 (8)0.0184 (7)
O10.0219 (6)0.0151 (5)0.0207 (6)0.0052 (5)0.0039 (5)0.0101 (5)
O20.0532 (10)0.0561 (10)0.0613 (10)0.0424 (9)0.0316 (9)0.0341 (9)
O30.142 (2)0.0701 (14)0.0598 (12)0.0690 (15)0.0659 (14)0.0498 (11)
O40.0513 (9)0.0468 (9)0.0512 (9)0.0369 (8)0.0337 (8)0.0324 (8)
C10.0264 (9)0.0306 (10)0.0197 (8)0.0037 (8)0.0019 (7)0.0118 (7)
C20.0325 (10)0.0184 (8)0.0238 (9)0.0033 (7)0.0054 (7)0.0059 (7)
C30.0179 (8)0.0207 (8)0.0233 (8)0.0018 (6)0.0037 (6)0.0116 (7)
C40.0199 (8)0.0140 (7)0.0173 (7)0.0071 (6)0.0083 (6)0.0071 (6)
C50.0255 (9)0.0210 (8)0.0274 (8)0.0107 (7)0.0126 (7)0.0107 (7)
C60.0298 (10)0.0285 (9)0.0355 (10)0.0108 (8)0.0190 (8)0.0174 (8)
C70.0311 (10)0.0245 (9)0.0415 (11)0.0093 (8)0.0157 (9)0.0220 (8)
C80.0274 (9)0.0195 (8)0.0395 (10)0.0117 (7)0.0121 (8)0.0168 (8)
C90.0184 (8)0.0157 (7)0.0197 (7)0.0068 (6)0.0040 (6)0.0078 (6)
C100.0184 (8)0.0185 (8)0.0171 (7)0.0082 (6)0.0031 (6)0.0051 (6)
C110.0294 (9)0.0224 (8)0.0260 (9)0.0150 (7)0.0069 (7)0.0067 (7)
C120.0360 (11)0.0380 (11)0.0286 (9)0.0253 (9)0.0128 (8)0.0077 (8)
C130.0296 (10)0.0435 (11)0.0285 (9)0.0193 (9)0.0161 (8)0.0117 (8)
C140.0264 (9)0.0296 (9)0.0260 (9)0.0114 (7)0.0134 (7)0.0116 (7)
Geometric parameters (Å, º) top
Cu—N21.9468 (13)C2—H2A0.9800
Cu—O1i2.0126 (12)C2—H2B0.9800
Cu—N12.0166 (14)C3—H3A0.9800
Cu—N32.0173 (14)C3—H3B0.9800
Cu—N42.2276 (15)C4—C4i1.520 (3)
N1—C11.474 (2)C5—C61.384 (2)
N1—H1A0.9100C5—H5A0.9400
N1—H1D0.9100C6—C71.379 (3)
N2—C41.297 (2)C6—H6A0.9400
N2—C31.461 (2)C7—C81.382 (3)
N3—C51.340 (2)C7—H7A0.9400
N3—C91.348 (2)C8—C91.392 (2)
N4—C141.343 (2)C8—H8A0.9400
N4—C101.343 (2)C9—C101.485 (2)
N5—O31.237 (2)C10—C111.392 (2)
N5—O41.247 (2)C11—C121.384 (3)
N5—O21.248 (2)C11—H11A0.9400
O1—C41.2759 (19)C12—C131.381 (3)
O1—Cui2.0126 (12)C12—H12A0.9400
C1—C21.520 (3)C13—C141.384 (3)
C1—H1B0.9800C13—H13A0.9400
C1—H1C0.9800C14—H14A0.9400
C2—C31.521 (3)
N2—Cu—O1i83.86 (5)H2A—C2—H2B107.6
N2—Cu—N192.71 (6)N2—C3—C2111.39 (14)
O1i—Cu—N1149.59 (6)N2—C3—H3A109.4
N2—Cu—N3175.79 (5)C2—C3—H3A109.4
O1i—Cu—N391.94 (5)N2—C3—H3B109.4
N1—Cu—N391.03 (6)C2—C3—H3B109.4
N2—Cu—N4103.52 (6)H3A—C3—H3B108.0
O1i—Cu—N4104.96 (5)O1—C4—N2128.00 (14)
N1—Cu—N4105.21 (6)O1—C4—C4i118.54 (17)
N3—Cu—N477.33 (6)N2—C4—C4i113.46 (16)
C1—N1—Cu118.87 (11)N3—C5—C6122.18 (17)
C1—N1—H1A107.6N3—C5—H5A118.9
Cu—N1—H1A107.6C6—C5—H5A118.9
C1—N1—H1D107.6C7—C6—C5118.87 (18)
Cu—N1—H1D107.6C7—C6—H6A120.6
H1A—N1—H1D107.0C5—C6—H6A120.6
C4—N2—C3120.14 (13)C6—C7—C8119.18 (17)
C4—N2—Cu113.98 (11)C6—C7—H7A120.4
C3—N2—Cu125.69 (11)C8—C7—H7A120.4
C5—N3—C9119.43 (14)C7—C8—C9119.45 (17)
C5—N3—Cu121.63 (12)C7—C8—H8A120.3
C9—N3—Cu118.82 (11)C9—C8—H8A120.3
C14—N4—C10118.89 (15)N3—C9—C8120.89 (16)
C14—N4—Cu128.93 (12)N3—C9—C10116.00 (14)
C10—N4—Cu112.17 (11)C8—C9—C10123.11 (16)
O3—N5—O4118.99 (18)N4—C10—C11121.92 (16)
O3—N5—O2121.84 (19)N4—C10—C9115.52 (14)
O4—N5—O2119.05 (16)C11—C10—C9122.56 (16)
C4—O1—Cui109.76 (10)C12—C11—C10118.44 (18)
N1—C1—C2112.38 (15)C12—C11—H11A120.8
N1—C1—H1B109.1C10—C11—H11A120.8
C2—C1—H1B109.1C13—C12—C11119.83 (18)
N1—C1—H1C109.1C13—C12—H12A120.1
C2—C1—H1C109.1C11—C12—H12A120.1
H1B—C1—H1C107.9C12—C13—C14118.41 (18)
C1—C2—C3114.27 (16)C12—C13—H13A120.8
C1—C2—H2A108.7C14—C13—H13A120.8
C3—C2—H2A108.7N4—C14—C13122.44 (18)
C1—C2—H2B108.7N4—C14—H14A118.8
C3—C2—H2B108.7C13—C14—H14A118.8
N2—Cu—N1—C133.22 (14)C3—N2—C4—O10.0 (3)
O1i—Cu—N1—C1115.69 (15)Cu—N2—C4—O1175.28 (14)
N3—Cu—N1—C1148.72 (14)C3—N2—C4—C4i179.98 (17)
N4—Cu—N1—C171.58 (14)Cu—N2—C4—C4i4.7 (2)
O1i—Cu—N2—C45.67 (12)C9—N3—C5—C60.5 (3)
N1—Cu—N2—C4144.03 (12)Cu—N3—C5—C6175.42 (14)
N4—Cu—N2—C4109.62 (12)N3—C5—C6—C70.4 (3)
O1i—Cu—N2—C3179.34 (15)C5—C6—C7—C80.1 (3)
N1—Cu—N2—C330.96 (15)C6—C7—C8—C90.5 (3)
N4—Cu—N2—C375.39 (15)C5—N3—C9—C80.1 (2)
O1i—Cu—N3—C578.01 (14)Cu—N3—C9—C8175.93 (13)
N1—Cu—N3—C571.72 (14)C5—N3—C9—C10179.56 (14)
N4—Cu—N3—C5177.08 (14)Cu—N3—C9—C103.55 (19)
O1i—Cu—N3—C9106.07 (12)C7—C8—C9—N30.4 (3)
N1—Cu—N3—C9104.20 (13)C7—C8—C9—C10179.05 (17)
N4—Cu—N3—C91.17 (12)C14—N4—C10—C112.0 (2)
N2—Cu—N4—C144.13 (16)Cu—N4—C10—C11176.53 (13)
O1i—Cu—N4—C1491.28 (15)C14—N4—C10—C9177.72 (15)
N1—Cu—N4—C1492.52 (15)Cu—N4—C10—C93.76 (17)
N3—Cu—N4—C14179.89 (16)N3—C9—C10—N44.9 (2)
N2—Cu—N4—C10174.20 (11)C8—C9—C10—N4174.57 (16)
O1i—Cu—N4—C1087.05 (12)N3—C9—C10—C11175.39 (15)
N1—Cu—N4—C1089.15 (12)C8—C9—C10—C115.1 (3)
N3—Cu—N4—C101.56 (11)N4—C10—C11—C122.8 (3)
Cu—N1—C1—C255.2 (2)C9—C10—C11—C12176.87 (16)
N1—C1—C2—C368.9 (2)C10—C11—C12—C131.0 (3)
C4—N2—C3—C2127.05 (17)C11—C12—C13—C141.4 (3)
Cu—N2—C3—C247.7 (2)C10—N4—C14—C130.7 (3)
C1—C2—C3—N262.5 (2)Cu—N4—C14—C13178.88 (14)
Cui—O1—C4—N2175.56 (14)C12—C13—C14—N42.3 (3)
Cui—O1—C4—C4i4.4 (2)
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O20.912.212.928 (2)135
N1—H1A···O2ii0.912.633.080 (2)111
N1—H1D···O4ii0.912.163.032 (2)161
C1—H1B···O4iii0.982.533.413 (3)150
C3—H3B···O4iii0.982.683.528 (2)145
C7—H7A···O4iv0.942.453.348 (2)160
C8—H8A···O3iv0.942.653.253 (3)122
Symmetry codes: (ii) x, y+1, z+1; (iii) x+1, y, z; (iv) x, y1, z.
 

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