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The crystal structure of the title compound, [Cu(NO
3)
2(C
12H
10N
6)
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 Cu
II 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
CCDC reference: 242021
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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)-4
H-1,2,4-triazole-
κ2N1,
N5]bis(nitrato-
κO)copper(II)
top
Crystal data top
[Cu(NO3)2(C12H10N6)2] | Z = 1 |
Mr = 664.09 | F(000) = 339 |
Triclinic, P1 | Dx = 1.688 Mg m−3 Dm = 1.69 (1) Mg m−3 Dm measured by flotation in a mixture of carbon tetrachloride and bromoform |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.940 (1) Å | Cell parameters from 6086 reflections |
b = 9.319 (2) Å | θ = 3.3–30.0° |
c = 10.765 (2) Å | µ = 0.91 mm−1 |
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 tube | Rint = 0.051 |
ω scans | θmax = 28.0°, θmin = 3.3° |
Absorption correction: numerical CrysAlis RED (Oxford Diffraction, 2003) | h = −8→9 |
Tmin = 0.884, Tmax = 0.973 | k = −12→11 |
5600 measured reflections | l = −11→14 |
3102 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: difmap (N-H) and geom (C-H) |
wR(F2) = 0.078 | H-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 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cu1 | 0.0000 | 0.0000 | 0.0000 | 0.0423 (3) | |
N1 | −0.1024 (4) | 0.0832 (3) | 0.1437 (2) | 0.036 (1) | |
N2 | −0.2734 (4) | 0.0481 (3) | 0.2027 (3) | 0.039 (1) | |
C3 | −0.2518 (5) | 0.1579 (4) | 0.2860 (3) | 0.037 (1) | |
N4 | −0.0695 (4) | 0.2626 (3) | 0.2821 (3) | 0.040 (1) | |
C5 | 0.0215 (5) | 0.2117 (4) | 0.1902 (3) | 0.035 (1) | |
N6 | 0.0179 (4) | 0.3967 (3) | 0.3563 (3) | 0.057 (1) | |
C7 | 0.2178 (5) | 0.2691 (4) | 0.1469 (3) | 0.038 (1) | |
N8 | 0.2453 (4) | 0.1783 (3) | 0.0538 (2) | 0.036 (1) | |
C9 | 0.4247 (5) | 0.2128 (4) | 0.0084 (3) | 0.041 (1) | |
H9 | 0.4398 | 0.1438 | −0.0601 | 0.049* | |
C10 | 0.5811 (5) | 0.3353 (4) | 0.0521 (4) | 0.049 (1) | |
H10 | 0.7024 | 0.3540 | 0.0180 | 0.059* | |
C11 | 0.5503 (5) | 0.4249 (4) | 0.1447 (4) | 0.050 (1) | |
H11 | 0.6524 | 0.5145 | 0.1806 | 0.060* | |
C12 | 0.3660 (5) | 0.3924 (4) | 0.1945 (3) | 0.047 (1) | |
H12 | 0.3492 | 0.4605 | 0.2631 | 0.057* | |
C13 | −0.4060 (6) | 0.1657 (4) | 0.3679 (3) | 0.041 (1) | |
N14 | −0.3536 (5) | 0.2743 (3) | 0.4589 (3) | 0.064 (1) | |
C15 | −0.4938 (7) | 0.2817 (5) | 0.5327 (4) | 0.087 (2) | |
H15 | −0.4565 | 0.3628 | 0.6017 | 0.104* | |
C16 | −0.6859 (7) | 0.1868 (5) | 0.5217 (4) | 0.077 (2) | |
H16 | −0.7760 | 0.2039 | 0.5776 | 0.092* | |
C17 | −0.7331 (6) | 0.0748 (5) | 0.4310 (4) | 0.057 (1) | |
H17 | −0.8594 | 0.0019 | 0.4184 | 0.069* | |
C18 | −0.5925 (5) | 0.0636 (4) | 0.3512 (3) | 0.042 (1) | |
H18 | −0.6266 | −0.0178 | 0.2826 | 0.050* | |
N20 | −0.0574 (5) | 0.2724 (5) | −0.1798 (4) | 0.061 (1) | |
H61 | −0.0743 | 0.4030 | 0.4181 | 0.073* | |
H62 | −0.0026 | 0.4610 | 0.2979 | 0.073* | |
O21 | −0.0486 (6) | 0.3979 (4) | −0.1450 (4) | 0.128 (2) | |
O22 | 0.0354 (6) | 0.2619 (4) | −0.2639 (3) | 0.137 (2) | |
O23 | −0.1483 (4) | 0.1648 (3) | −0.1218 (3) | 0.065 (1) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0363 (5) | 0.0375 (5) | 0.0420 (5) | 0.0018 (4) | 0.0114 (4) | −0.0104 (4) |
N1 | 0.033 (2) | 0.036 (2) | 0.033 (2) | 0.007 (2) | 0.011 (2) | −0.005 (2) |
N2 | 0.038 (2) | 0.033 (2) | 0.036 (2) | 0.003 (2) | 0.009 (2) | −0.014 (2) |
C3 | 0.038 (2) | 0.031 (2) | 0.037 (2) | 0.006 (2) | 0.007 (2) | 0.002 (2) |
N4 | 0.041 (2) | 0.031 (2) | 0.041 (2) | 0.004 (2) | 0.010 (2) | −0.008 (2) |
C5 | 0.034 (2) | 0.031 (2) | 0.033 (2) | 0.005 (2) | 0.004 (2) | −0.004 (2) |
N6 | 0.057 (2) | 0.038 (2) | 0.058 (2) | −0.001 (2) | 0.010 (2) | −0.023 (2) |
C7 | 0.034 (2) | 0.035 (2) | 0.037 (2) | 0.008 (2) | 0.002 (2) | −0.007 (2) |
N8 | 0.033 (2) | 0.030 (2) | 0.035 (2) | 0.002 (2) | 0.006 (2) | −0.006 (2) |
C9 | 0.036 (2) | 0.037 (2) | 0.046 (3) | 0.011 (2) | 0.009 (2) | −0.004 (2) |
C10 | 0.034 (2) | 0.043 (3) | 0.063 (3) | 0.004 (2) | 0.012 (2) | −0.001 (2) |
C11 | 0.045 (3) | 0.032 (2) | 0.060 (3) | 0.002 (2) | −0.001 (2) | −0.007 (2) |
C12 | 0.035 (3) | 0.038 (2) | 0.054 (3) | 0.001 (2) | 0.009 (2) | −0.014 (2) |
C13 | 0.046 (3) | 0.038 (2) | 0.036 (2) | 0.011 (2) | 0.015 (2) | −0.004 (2) |
N14 | 0.060 (2) | 0.060 (2) | 0.051 (2) | 0.002 (2) | 0.026 (2) | −0.025 (2) |
C15 | 0.085 (4) | 0.069 (3) | 0.073 (3) | −0.007 (3) | 0.041 (3) | −0.039 (3) |
C16 | 0.079 (4) | 0.075 (3) | 0.076 (3) | 0.031 (3) | 0.040 (3) | −0.017 (3) |
C17 | 0.048 (3) | 0.061 (3) | 0.058 (3) | 0.011 (2) | 0.018 (2) | 0.001 (2) |
C18 | 0.041 (2) | 0.048 (3) | 0.032 (2) | 0.011 (2) | 0.010 (2) | −0.004 (2) |
N20 | 0.053 (3) | 0.050 (3) | 0.067 (3) | 0.006 (2) | 0.018 (2) | −0.012 (2) |
O21 | 0.143 (3) | 0.058 (2) | 0.185 (4) | 0.023 (2) | 0.104 (3) | 0.001 (2) |
O22 | 0.143 (3) | 0.113 (3) | 0.119 (3) | −0.005 (3) | 0.089 (3) | −0.042 (2) |
O23 | 0.052 (2) | 0.050 (2) | 0.080 (2) | −0.002 (2) | 0.005 (2) | 0.006 (2) |
Geometric parameters (Å, º) top
Cu1—N1 | 1.899 (3) | C9—H9 | 0.93 |
Cu1—N1i | 1.899 (3) | C10—C11 | 1.266 (4) |
Cu1—N8 | 1.983 (3) | C10—H10 | 0.93 |
Cu1—N8i | 1.983 (3) | C11—C12 | 1.402 (4) |
Cu1—O23 | 2.541 (3) | C11—H11 | 0.93 |
Cu1—O23i | 2.541 (3) | C12—H12 | 0.93 |
N1—C5 | 1.256 (4) | C13—N14 | 1.236 (4) |
N1—N2 | 1.377 (3) | C13—C18 | 1.352 (5) |
N2—C3 | 1.211 (4) | N14—C15 | 1.317 (4) |
C3—N4 | 1.373 (4) | C15—C16 | 1.361 (5) |
C3—C13 | 1.452 (4) | C15—H15 | 0.93 |
N4—C5 | 1.313 (4) | C16—C17 | 1.254 (4) |
N4—N6 | 1.318 (3) | C16—H16 | 0.93 |
C5—C7 | 1.462 (5) | C17—C18 | 1.368 (4) |
N6—H62 | 0.96 | C17—H17 | 0.93 |
N6—H61 | 0.97 | C18—H18 | 0.93 |
C7—N8 | 1.267 (3) | N20—O21 | 1.151 (4) |
C7—C12 | 1.303 (4) | N20—O22 | 1.162 (4) |
N8—C9 | 1.350 (4) | N20—O23 | 1.307 (4) |
C9—C10 | 1.322 (4) | | |
| | | |
N1—Cu1—N1i | 180.0 | C7—N8—C9 | 119.1 (3) |
N1—Cu1—N8 | 86.1 (1) | C7—N8—Cu1 | 110.1 (2) |
N1—Cu1—N8i | 93.9 (1) | C9—N8—Cu1 | 130.8 (2) |
N1i—Cu1—N8 | 93.9 (1) | C10—C9—N8 | 126.2 (3) |
N1i—Cu1—N8i | 86.1 (1) | C10—C9—H9 | 117 |
N1—Cu1—O23 | 87.0 (1) | N8—C9—H9 | 117 |
N1—Cu1—O23i | 93.1 (1) | C11—C10—C9 | 113.7 (4) |
N1i—Cu1—O23 | 93.1 (1) | C11—C10—H10 | 123 |
N1i—Cu1—O23i | 87.0 (1) | C9—C10—H10 | 123 |
N8—Cu1—N8i | 180.0 | C10—C11—C12 | 121.6 (4) |
N8—Cu1—O23 | 87.4 (1) | C10—C11—H11 | 119 |
N8—Cu1—O23i | 92.6 (1) | C12—C11—H11 | 119 |
N8i—Cu1—O23 | 92.6 (1) | C7—C12—C11 | 121.6 (3) |
N8i—Cu1—O23i | 87.4 (1) | C7—C12—H12 | 119 |
O23—Cu1—O23i | 180.0 | C11—C12—H12 | 119 |
C5—N1—N2 | 114.3 (3) | N14—C13—C18 | 120.6 (4) |
C5—N1—Cu1 | 106.9 (2) | N14—C13—C3 | 114.6 (4) |
N2—N1—Cu1 | 138.6 (2) | C18—C13—C3 | 124.7 (3) |
C3—N2—N1 | 105.1 (3) | C13—N14—C15 | 114.6 (4) |
N2—C3—N4 | 108.1 (3) | N14—C15—C16 | 128.8 (4) |
N2—C3—C13 | 121.6 (4) | N14—C15—H15 | 116 |
N4—C3—C13 | 130.4 (3) | C16—C15—H15 | 116 |
C5—N4—N6 | 120.2 (3) | C17—C16—C15 | 115.3 (4) |
C5—N4—C3 | 110.7 (3) | C17—C16—H16 | 122 |
N6—N4—C3 | 129.2 (3) | C15—C16—H16 | 122 |
N1—C5—N4 | 101.9 (3) | C16—C17—C18 | 117.8 (4) |
N1—C5—C7 | 123.6 (3) | C16—C17—H17 | 121 |
N4—C5—C7 | 134.4 (3) | C18—C17—H17 | 121 |
N4—N6—H62 | 99 | C13—C18—C17 | 122.8 (3) |
N4—N6—H61 | 104 | C13—C18—H18 | 119 |
H62—N6—H61 | 107 | C17—C18—H18 | 119 |
N8—C7—C12 | 117.8 (3) | O21—N20—O22 | 110.1 (5) |
N8—C7—C5 | 112.7 (3) | O21—N20—O23 | 121.9 (4) |
C12—C7—C5 | 129.4 (3) | O22—N20—O23 | 127.8 (4) |
Symmetry code: (i) −x, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H61···N14 | 0.97 | 2.10 | 2.901 (4) | 139 |
C9—H9···N2i | 0.93 | 2.13 | 2.923 (4) | 143 |
N6—H62···O21ii | 0.96 | 2.26 | 3.186 (5) | 161 |
C10—H10···O21iii | 0.93 | 2.57 | 3.454 (6) | 160 |
C16—H16···O22iv | 0.93 | 2.32 | 3.247 (5) | 173 |
C18—H18···O23v | 0.93 | 2.21 | 3.043 (4) | 149 |
C11—H11···O22vi | 0.93 | 2.52 | 3.447 (5) | 172 |
Symmetry codes: (i) −x, −y, −z; (ii) −x, −y+1, −z; (iii) x+1, y, z; (iv) x−1, y, z+1; (v) −x−1, −y, −z; (vi) −x+1, −y+1, −z. |
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