Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804010220/hb6038sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804010220/hb6038Isup2.hkl |
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).
[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 |
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 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 |
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. |
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) |
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) |
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. |
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. |