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The crystal structure of the title compound, [Cu(NO3)2(C12H10N6)2], consists of neutral mononuclear mol­ecules held together by means of an extensive three-dimensional network of N—H...O hydrogen bonds, C—H...O interactions and face-to-face π–π interactions. The CuII atom, which lies at a center of inversion, has a distorted octahedral geometry, where the equatorial plane is composed of four N atoms belonging to two bidentate 4-amino-3,5-bis(2-pyridyl)-1,2,4-triazole ligands, and the axial positions are occupied by two O atoms of two monodentate nitrate anions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804010220/hb6038sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804010220/hb6038Isup2.hkl
Contains datablock I

CCDC reference: 242021

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.046
  • wR factor = 0.078
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 38 Perc. PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... N20 PLAT411_ALERT_2_B Short Inter H...H Contact H12 .. H15 .. 1.93 Ang.
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C11 - C12 .. 5.12 su PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C15 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.81
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 3 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 5 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

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

trans-bis[4-amino-3,5-bis(2-pyridyl)-4H-1,2,4-triazole- κ2N1,N5]bis(nitrato-κO)copper(II) top
Crystal data top
[Cu(NO3)2(C12H10N6)2]Z = 1
Mr = 664.09F(000) = 339
Triclinic, P1Dx = 1.688 Mg m3
Dm = 1.69 (1) Mg m3
Dm measured by flotation in a mixture of carbon tetrachloride and bromoform
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.940 (1) ÅCell parameters from 6086 reflections
b = 9.319 (2) Åθ = 3.3–30.0°
c = 10.765 (2) ŵ = 0.91 mm1
α = 99.36 (1)°T = 293 K
β = 94.86 (2)°Plate, light blue
γ = 106.27 (2)°0.20 × 0.10 × 0.02 mm
V = 653.2 (2) Å3
Data collection top
Xcalibur
diffractometer
1192 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.051
ω scansθmax = 28.0°, θmin = 3.3°
Absorption correction: numerical
CrysAlis RED (Oxford Diffraction, 2003)
h = 89
Tmin = 0.884, Tmax = 0.973k = 1211
5600 measured reflectionsl = 1114
3102 independent 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)] = 0.046Hydrogen site location: difmap (N-H) and geom (C-H)
wR(F2) = 0.078H-atom parameters constrained
S = 0.81 w = 1/[σ2(Fo2) + (0.0159P)2]
where P = (Fo2 + 2Fc2)/3
3102 reflections(Δ/σ)max < 0.001
205 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.32 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
Cu10.00000.00000.00000.0423 (3)
N10.1024 (4)0.0832 (3)0.1437 (2)0.036 (1)
N20.2734 (4)0.0481 (3)0.2027 (3)0.039 (1)
C30.2518 (5)0.1579 (4)0.2860 (3)0.037 (1)
N40.0695 (4)0.2626 (3)0.2821 (3)0.040 (1)
C50.0215 (5)0.2117 (4)0.1902 (3)0.035 (1)
N60.0179 (4)0.3967 (3)0.3563 (3)0.057 (1)
C70.2178 (5)0.2691 (4)0.1469 (3)0.038 (1)
N80.2453 (4)0.1783 (3)0.0538 (2)0.036 (1)
C90.4247 (5)0.2128 (4)0.0084 (3)0.041 (1)
H90.43980.14380.06010.049*
C100.5811 (5)0.3353 (4)0.0521 (4)0.049 (1)
H100.70240.35400.01800.059*
C110.5503 (5)0.4249 (4)0.1447 (4)0.050 (1)
H110.65240.51450.18060.060*
C120.3660 (5)0.3924 (4)0.1945 (3)0.047 (1)
H120.34920.46050.26310.057*
C130.4060 (6)0.1657 (4)0.3679 (3)0.041 (1)
N140.3536 (5)0.2743 (3)0.4589 (3)0.064 (1)
C150.4938 (7)0.2817 (5)0.5327 (4)0.087 (2)
H150.45650.36280.60170.104*
C160.6859 (7)0.1868 (5)0.5217 (4)0.077 (2)
H160.77600.20390.57760.092*
C170.7331 (6)0.0748 (5)0.4310 (4)0.057 (1)
H170.85940.00190.41840.069*
C180.5925 (5)0.0636 (4)0.3512 (3)0.042 (1)
H180.62660.01780.28260.050*
N200.0574 (5)0.2724 (5)0.1798 (4)0.061 (1)
H610.07430.40300.41810.073*
H620.00260.46100.29790.073*
O210.0486 (6)0.3979 (4)0.1450 (4)0.128 (2)
O220.0354 (6)0.2619 (4)0.2639 (3)0.137 (2)
O230.1483 (4)0.1648 (3)0.1218 (3)0.065 (1)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0363 (5)0.0375 (5)0.0420 (5)0.0018 (4)0.0114 (4)0.0104 (4)
N10.033 (2)0.036 (2)0.033 (2)0.007 (2)0.011 (2)0.005 (2)
N20.038 (2)0.033 (2)0.036 (2)0.003 (2)0.009 (2)0.014 (2)
C30.038 (2)0.031 (2)0.037 (2)0.006 (2)0.007 (2)0.002 (2)
N40.041 (2)0.031 (2)0.041 (2)0.004 (2)0.010 (2)0.008 (2)
C50.034 (2)0.031 (2)0.033 (2)0.005 (2)0.004 (2)0.004 (2)
N60.057 (2)0.038 (2)0.058 (2)0.001 (2)0.010 (2)0.023 (2)
C70.034 (2)0.035 (2)0.037 (2)0.008 (2)0.002 (2)0.007 (2)
N80.033 (2)0.030 (2)0.035 (2)0.002 (2)0.006 (2)0.006 (2)
C90.036 (2)0.037 (2)0.046 (3)0.011 (2)0.009 (2)0.004 (2)
C100.034 (2)0.043 (3)0.063 (3)0.004 (2)0.012 (2)0.001 (2)
C110.045 (3)0.032 (2)0.060 (3)0.002 (2)0.001 (2)0.007 (2)
C120.035 (3)0.038 (2)0.054 (3)0.001 (2)0.009 (2)0.014 (2)
C130.046 (3)0.038 (2)0.036 (2)0.011 (2)0.015 (2)0.004 (2)
N140.060 (2)0.060 (2)0.051 (2)0.002 (2)0.026 (2)0.025 (2)
C150.085 (4)0.069 (3)0.073 (3)0.007 (3)0.041 (3)0.039 (3)
C160.079 (4)0.075 (3)0.076 (3)0.031 (3)0.040 (3)0.017 (3)
C170.048 (3)0.061 (3)0.058 (3)0.011 (2)0.018 (2)0.001 (2)
C180.041 (2)0.048 (3)0.032 (2)0.011 (2)0.010 (2)0.004 (2)
N200.053 (3)0.050 (3)0.067 (3)0.006 (2)0.018 (2)0.012 (2)
O210.143 (3)0.058 (2)0.185 (4)0.023 (2)0.104 (3)0.001 (2)
O220.143 (3)0.113 (3)0.119 (3)0.005 (3)0.089 (3)0.042 (2)
O230.052 (2)0.050 (2)0.080 (2)0.002 (2)0.005 (2)0.006 (2)
Geometric parameters (Å, º) top
Cu1—N11.899 (3)C9—H90.93
Cu1—N1i1.899 (3)C10—C111.266 (4)
Cu1—N81.983 (3)C10—H100.93
Cu1—N8i1.983 (3)C11—C121.402 (4)
Cu1—O232.541 (3)C11—H110.93
Cu1—O23i2.541 (3)C12—H120.93
N1—C51.256 (4)C13—N141.236 (4)
N1—N21.377 (3)C13—C181.352 (5)
N2—C31.211 (4)N14—C151.317 (4)
C3—N41.373 (4)C15—C161.361 (5)
C3—C131.452 (4)C15—H150.93
N4—C51.313 (4)C16—C171.254 (4)
N4—N61.318 (3)C16—H160.93
C5—C71.462 (5)C17—C181.368 (4)
N6—H620.96C17—H170.93
N6—H610.97C18—H180.93
C7—N81.267 (3)N20—O211.151 (4)
C7—C121.303 (4)N20—O221.162 (4)
N8—C91.350 (4)N20—O231.307 (4)
C9—C101.322 (4)
N1—Cu1—N1i180.0C7—N8—C9119.1 (3)
N1—Cu1—N886.1 (1)C7—N8—Cu1110.1 (2)
N1—Cu1—N8i93.9 (1)C9—N8—Cu1130.8 (2)
N1i—Cu1—N893.9 (1)C10—C9—N8126.2 (3)
N1i—Cu1—N8i86.1 (1)C10—C9—H9117
N1—Cu1—O2387.0 (1)N8—C9—H9117
N1—Cu1—O23i93.1 (1)C11—C10—C9113.7 (4)
N1i—Cu1—O2393.1 (1)C11—C10—H10123
N1i—Cu1—O23i87.0 (1)C9—C10—H10123
N8—Cu1—N8i180.0C10—C11—C12121.6 (4)
N8—Cu1—O2387.4 (1)C10—C11—H11119
N8—Cu1—O23i92.6 (1)C12—C11—H11119
N8i—Cu1—O2392.6 (1)C7—C12—C11121.6 (3)
N8i—Cu1—O23i87.4 (1)C7—C12—H12119
O23—Cu1—O23i180.0C11—C12—H12119
C5—N1—N2114.3 (3)N14—C13—C18120.6 (4)
C5—N1—Cu1106.9 (2)N14—C13—C3114.6 (4)
N2—N1—Cu1138.6 (2)C18—C13—C3124.7 (3)
C3—N2—N1105.1 (3)C13—N14—C15114.6 (4)
N2—C3—N4108.1 (3)N14—C15—C16128.8 (4)
N2—C3—C13121.6 (4)N14—C15—H15116
N4—C3—C13130.4 (3)C16—C15—H15116
C5—N4—N6120.2 (3)C17—C16—C15115.3 (4)
C5—N4—C3110.7 (3)C17—C16—H16122
N6—N4—C3129.2 (3)C15—C16—H16122
N1—C5—N4101.9 (3)C16—C17—C18117.8 (4)
N1—C5—C7123.6 (3)C16—C17—H17121
N4—C5—C7134.4 (3)C18—C17—H17121
N4—N6—H6299C13—C18—C17122.8 (3)
N4—N6—H61104C13—C18—H18119
H62—N6—H61107C17—C18—H18119
N8—C7—C12117.8 (3)O21—N20—O22110.1 (5)
N8—C7—C5112.7 (3)O21—N20—O23121.9 (4)
C12—C7—C5129.4 (3)O22—N20—O23127.8 (4)
Symmetry code: (i) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N6—H61···N140.972.102.901 (4)139
C9—H9···N2i0.932.132.923 (4)143
N6—H62···O21ii0.962.263.186 (5)161
C10—H10···O21iii0.932.573.454 (6)160
C16—H16···O22iv0.932.323.247 (5)173
C18—H18···O23v0.932.213.043 (4)149
C11—H11···O22vi0.932.523.447 (5)172
Symmetry codes: (i) x, y, z; (ii) x, y+1, z; (iii) x+1, y, z; (iv) x1, y, z+1; (v) x1, y, z; (vi) x+1, y+1, z.
 

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