Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806018083/bi2008sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806018083/bi2008Isup2.hkl |
CCDC reference: 610695
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.040
- wR factor = 0.071
- Data-to-parameter ratio = 12.0
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT241_ALERT_2_A Check High Ueq as Compared to Neighbors for O2
Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N1
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.736 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu1 - O1 .. 9.50 su PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for P1 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.24
1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 0 ALERT type 3 Indicator that the structure quality may be low 1 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: SIR92 (Altomare et al., 1993); 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)(C10H8N2)2]PF6 | Z = 2 |
Mr = 582.89 | F(000) = 586 |
Triclinic, P1 | Dx = 1.756 Mg m−3 Dm = 1.75 (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 = 7.449 (1) Å | Cell parameters from 9454 reflections |
b = 11.329 (2) Å | θ = 3.4–28.0° |
c = 14.564 (2) Å | µ = 1.15 mm−1 |
α = 111.27 (2)° | T = 293 K |
β = 99.16 (1)° | Prism, blue |
γ = 98.52 (2)° | 0.30 × 0.20 × 0.20 mm |
V = 1102.0 (3) Å3 |
Oxford Diffraction Xcalibur CCD diffractometer | 1939 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.040 |
Graphite monochromator | θmax = 25.0°, θmin = 3.4° |
ω scans | h = −8→8 |
7697 measured reflections | k = −12→13 |
3894 independent reflections | l = −17→16 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.071 | H-atom parameters constrained |
S = 0.74 | w = 1/[σ2(Fo2) + (0.0217P)2] where P = (Fo2 + 2Fc2)/3 |
3894 reflections | (Δ/σ)max < 0.001 |
325 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 | −0.02925 (7) | 0.35229 (4) | 0.71969 (3) | 0.04549 (17) | |
N11 | 0.0529 (4) | 0.5280 (3) | 0.8296 (2) | 0.0403 (8) | |
C12 | 0.0069 (5) | 0.6334 (4) | 0.8218 (3) | 0.0519 (11) | |
H12 | −0.0663 | 0.6254 | 0.7609 | 0.062* | |
C13 | 0.0632 (6) | 0.7537 (4) | 0.9000 (3) | 0.0584 (12) | |
H13 | 0.0304 | 0.8261 | 0.8922 | 0.070* | |
C14 | 0.1685 (6) | 0.7643 (4) | 0.9894 (3) | 0.0593 (12) | |
H14 | 0.2099 | 0.8449 | 1.0433 | 0.071* | |
C15 | 0.2130 (5) | 0.6565 (4) | 0.9996 (3) | 0.0520 (11) | |
H15 | 0.2832 | 0.6630 | 1.0607 | 0.062* | |
C16 | 0.1535 (5) | 0.5376 (4) | 0.9185 (3) | 0.0395 (10) | |
C17 | 0.1918 (5) | 0.4144 (4) | 0.9203 (3) | 0.0386 (10) | |
N18 | 0.1138 (4) | 0.3084 (3) | 0.8345 (2) | 0.0401 (8) | |
C19 | 0.1441 (5) | 0.1950 (4) | 0.8319 (3) | 0.0541 (11) | |
H19 | 0.0926 | 0.1217 | 0.7724 | 0.065* | |
C110 | 0.2481 (6) | 0.1793 (5) | 0.9127 (4) | 0.0616 (13) | |
H110 | 0.2651 | 0.0978 | 0.9081 | 0.074* | |
C111 | 0.3249 (6) | 0.2878 (5) | 0.9995 (4) | 0.0623 (13) | |
H111 | 0.3958 | 0.2813 | 1.0553 | 0.075* | |
C112 | 0.2966 (5) | 0.4061 (4) | 1.0036 (3) | 0.0534 (11) | |
H112 | 0.3479 | 0.4804 | 1.0624 | 0.064* | |
N21 | −0.1220 (4) | 0.1797 (3) | 0.6063 (2) | 0.0361 (8) | |
C22 | −0.2269 (5) | 0.0757 (4) | 0.6085 (3) | 0.0460 (11) | |
H22 | −0.2516 | 0.0796 | 0.6700 | 0.055* | |
C23 | −0.3004 (5) | −0.0372 (4) | 0.5243 (3) | 0.0495 (11) | |
H23 | −0.3672 | −0.1100 | 0.5292 | 0.059* | |
C24 | −0.2733 (5) | −0.0402 (4) | 0.4333 (3) | 0.0533 (11) | |
H24 | −0.3260 | −0.1141 | 0.3744 | 0.064* | |
C25 | −0.1674 (5) | 0.0671 (4) | 0.4295 (3) | 0.0434 (10) | |
H25 | −0.1484 | 0.0663 | 0.3677 | 0.052* | |
C26 | −0.0896 (5) | 0.1757 (3) | 0.5168 (3) | 0.0336 (9) | |
C27 | 0.0337 (5) | 0.2922 (3) | 0.5213 (3) | 0.0334 (9) | |
N28 | 0.0777 (4) | 0.3922 (3) | 0.6120 (2) | 0.0359 (8) | |
C29 | 0.1961 (5) | 0.5012 (4) | 0.6236 (3) | 0.0465 (10) | |
H29 | 0.2289 | 0.5705 | 0.6865 | 0.056* | |
C210 | 0.2702 (5) | 0.5144 (4) | 0.5469 (3) | 0.0490 (11) | |
H210 | 0.3491 | 0.5919 | 0.5569 | 0.059* | |
C211 | 0.2261 (5) | 0.4120 (4) | 0.4555 (3) | 0.0492 (11) | |
H211 | 0.2770 | 0.4181 | 0.4027 | 0.059* | |
C212 | 0.1064 (5) | 0.2996 (4) | 0.4419 (3) | 0.0439 (10) | |
H212 | 0.0746 | 0.2291 | 0.3797 | 0.053* | |
N1 | −0.4096 (6) | 0.3623 (3) | 0.7161 (3) | 0.0562 (10) | |
O1 | −0.2863 (4) | 0.3329 (3) | 0.76766 (19) | 0.0653 (9) | |
O2 | −0.3723 (5) | 0.3850 (3) | 0.6454 (3) | 0.1046 (13) | |
O3 | −0.5565 (5) | 0.3685 (3) | 0.7409 (3) | 0.1016 (13) | |
P1 | 0.5670 (2) | 0.87295 (11) | 0.77532 (9) | 0.0613 (4) | |
F1 | 0.3534 (4) | 0.8318 (3) | 0.7660 (2) | 0.1332 (12) | |
F2 | 0.5255 (4) | 0.8221 (2) | 0.65682 (16) | 0.0926 (9) | |
F3 | 0.7804 (4) | 0.9140 (3) | 0.7794 (2) | 0.1284 (12) | |
F4 | 0.6112 (6) | 0.9222 (2) | 0.89169 (17) | 0.1473 (15) | |
F5 | 0.5463 (4) | 1.0116 (2) | 0.78152 (18) | 0.0944 (9) | |
F6 | 0.5899 (4) | 0.7335 (2) | 0.76672 (19) | 0.1167 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0606 (4) | 0.0420 (3) | 0.0330 (3) | 0.0109 (2) | 0.0131 (3) | 0.0131 (3) |
N11 | 0.053 (2) | 0.037 (2) | 0.0296 (19) | 0.0097 (17) | 0.0120 (17) | 0.0102 (17) |
C12 | 0.063 (3) | 0.048 (3) | 0.039 (3) | 0.011 (2) | 0.010 (2) | 0.013 (2) |
C13 | 0.070 (3) | 0.043 (3) | 0.058 (3) | 0.010 (2) | 0.023 (3) | 0.012 (3) |
C14 | 0.060 (3) | 0.043 (3) | 0.054 (3) | −0.007 (2) | 0.015 (3) | 0.001 (3) |
C15 | 0.045 (3) | 0.064 (3) | 0.032 (2) | −0.002 (2) | 0.003 (2) | 0.010 (2) |
C16 | 0.034 (2) | 0.050 (3) | 0.032 (2) | 0.002 (2) | 0.013 (2) | 0.014 (2) |
C17 | 0.031 (2) | 0.056 (3) | 0.034 (2) | 0.007 (2) | 0.015 (2) | 0.021 (2) |
N18 | 0.043 (2) | 0.047 (2) | 0.036 (2) | 0.0158 (17) | 0.0152 (17) | 0.0175 (18) |
C19 | 0.062 (3) | 0.059 (3) | 0.043 (3) | 0.019 (2) | 0.018 (2) | 0.018 (2) |
C110 | 0.066 (3) | 0.074 (4) | 0.070 (3) | 0.031 (3) | 0.024 (3) | 0.048 (3) |
C111 | 0.047 (3) | 0.100 (4) | 0.066 (3) | 0.024 (3) | 0.016 (3) | 0.058 (3) |
C112 | 0.047 (3) | 0.072 (3) | 0.042 (3) | 0.007 (2) | 0.008 (2) | 0.026 (3) |
N21 | 0.041 (2) | 0.0325 (19) | 0.0352 (19) | 0.0071 (15) | 0.0115 (16) | 0.0137 (16) |
C22 | 0.052 (3) | 0.050 (3) | 0.049 (3) | 0.015 (2) | 0.020 (2) | 0.029 (2) |
C23 | 0.042 (3) | 0.040 (3) | 0.063 (3) | 0.006 (2) | 0.013 (2) | 0.018 (3) |
C24 | 0.048 (3) | 0.046 (3) | 0.054 (3) | 0.005 (2) | 0.005 (2) | 0.011 (2) |
C25 | 0.047 (3) | 0.044 (3) | 0.036 (2) | 0.009 (2) | 0.009 (2) | 0.012 (2) |
C26 | 0.038 (2) | 0.034 (2) | 0.029 (2) | 0.0124 (19) | 0.0059 (19) | 0.010 (2) |
C27 | 0.035 (2) | 0.035 (2) | 0.032 (2) | 0.0108 (19) | 0.0075 (19) | 0.014 (2) |
N28 | 0.037 (2) | 0.0330 (19) | 0.0327 (19) | 0.0055 (16) | 0.0055 (16) | 0.0088 (16) |
C29 | 0.045 (3) | 0.042 (3) | 0.040 (2) | 0.003 (2) | 0.000 (2) | 0.009 (2) |
C210 | 0.049 (3) | 0.050 (3) | 0.055 (3) | 0.008 (2) | 0.015 (2) | 0.030 (3) |
C211 | 0.052 (3) | 0.067 (3) | 0.047 (3) | 0.018 (2) | 0.022 (2) | 0.038 (3) |
C212 | 0.060 (3) | 0.041 (3) | 0.033 (2) | 0.014 (2) | 0.016 (2) | 0.013 (2) |
N1 | 0.062 (3) | 0.048 (2) | 0.060 (3) | 0.017 (2) | 0.018 (2) | 0.018 (2) |
O1 | 0.072 (2) | 0.083 (2) | 0.0449 (18) | 0.0337 (18) | 0.0119 (17) | 0.0244 (17) |
O2 | 0.136 (3) | 0.137 (3) | 0.096 (3) | 0.060 (3) | 0.056 (3) | 0.085 (3) |
O3 | 0.060 (2) | 0.123 (3) | 0.140 (3) | 0.036 (2) | 0.042 (2) | 0.059 (3) |
P1 | 0.0878 (11) | 0.0422 (8) | 0.0483 (8) | 0.0038 (7) | 0.0134 (7) | 0.0168 (6) |
F1 | 0.114 (3) | 0.120 (3) | 0.161 (3) | −0.008 (2) | 0.066 (2) | 0.051 (2) |
F2 | 0.145 (3) | 0.0741 (18) | 0.0516 (16) | 0.0169 (17) | 0.0195 (17) | 0.0215 (15) |
F3 | 0.077 (2) | 0.121 (3) | 0.171 (3) | 0.0052 (18) | 0.002 (2) | 0.057 (2) |
F4 | 0.312 (5) | 0.0632 (19) | 0.0377 (16) | −0.006 (2) | 0.013 (2) | 0.0168 (15) |
F5 | 0.146 (3) | 0.0507 (17) | 0.094 (2) | 0.0305 (16) | 0.0321 (19) | 0.0313 (16) |
F6 | 0.200 (3) | 0.0496 (17) | 0.083 (2) | 0.0221 (18) | −0.014 (2) | 0.0280 (16) |
Cu1—N11 | 1.979 (3) | C22—H22 | 0.930 |
Cu1—N18 | 2.092 (3) | C23—C24 | 1.361 (5) |
Cu1—N21 | 1.980 (3) | C23—H23 | 0.930 |
Cu1—N28 | 2.025 (3) | C24—C25 | 1.372 (5) |
Cu1—O1 | 2.148 (3) | C24—H24 | 0.930 |
N11—C12 | 1.328 (4) | C25—C26 | 1.373 (4) |
N11—C16 | 1.347 (4) | C25—H25 | 0.930 |
C12—C13 | 1.372 (5) | C26—C27 | 1.465 (4) |
C12—H12 | 0.930 | C27—N28 | 1.343 (4) |
C13—C14 | 1.363 (5) | C27—C212 | 1.376 (4) |
C13—H13 | 0.930 | N28—C29 | 1.346 (4) |
C14—C15 | 1.364 (5) | C29—C210 | 1.367 (5) |
C14—H14 | 0.930 | C29—H29 | 0.930 |
C15—C16 | 1.381 (5) | C210—C211 | 1.361 (5) |
C15—H15 | 0.930 | C210—H210 | 0.930 |
C16—C17 | 1.474 (5) | C211—C212 | 1.371 (5) |
C17—N18 | 1.347 (4) | C211—H211 | 0.930 |
C17—C112 | 1.376 (5) | C212—H212 | 0.930 |
N18—C19 | 1.325 (4) | N1—O3 | 1.209 (4) |
C19—C110 | 1.385 (5) | N1—O2 | 1.211 (4) |
C19—H19 | 0.930 | N1—O1 | 1.254 (4) |
C110—C111 | 1.368 (5) | O3—Cu1i | 3.457 (3) |
C110—H110 | 0.930 | P1—F4 | 1.541 (2) |
C111—C112 | 1.368 (5) | P1—F1 | 1.560 (3) |
C111—H111 | 0.930 | P1—F2 | 1.569 (2) |
C112—H112 | 0.930 | P1—F5 | 1.573 (2) |
N21—C22 | 1.328 (4) | P1—F3 | 1.574 (3) |
N21—C26 | 1.349 (4) | P1—F6 | 1.576 (3) |
C22—C23 | 1.372 (5) | ||
N11—Cu1—N18 | 80.03 (13) | C23—C22—H22 | 118.5 |
N21—Cu1—N18 | 102.77 (13) | C24—C23—C22 | 118.4 (4) |
N28—Cu1—N18 | 126.41 (11) | C24—C23—H23 | 120.8 |
N11—Cu1—N21 | 176.97 (13) | C22—C23—H23 | 120.8 |
N11—Cu1—N28 | 98.32 (12) | C23—C24—C25 | 119.2 (4) |
N21—Cu1—N28 | 80.99 (12) | C23—C24—H24 | 120.4 |
N11—Cu1—O1 | 88.16 (11) | C25—C24—H24 | 120.4 |
N18—Cu1—O1 | 92.77 (11) | C24—C25—C26 | 120.1 (4) |
N21—Cu1—O1 | 90.55 (12) | C24—C25—H25 | 120.0 |
N28—Cu1—O1 | 140.81 (11) | C26—C25—H25 | 120.0 |
C12—N11—C16 | 119.2 (3) | N21—C26—C25 | 120.5 (3) |
C12—N11—Cu1 | 123.9 (3) | N21—C26—C27 | 115.4 (3) |
C16—N11—Cu1 | 116.8 (3) | C25—C26—C27 | 124.1 (3) |
N11—C12—C13 | 122.6 (4) | N28—C27—C212 | 121.6 (3) |
N11—C12—H12 | 118.7 | N28—C27—C26 | 114.2 (3) |
C13—C12—H12 | 118.7 | C212—C27—C26 | 124.1 (3) |
C14—C13—C12 | 118.4 (4) | C27—N28—C29 | 118.0 (3) |
C14—C13—H13 | 120.8 | C27—N28—Cu1 | 114.2 (2) |
C12—C13—H13 | 120.8 | C29—N28—Cu1 | 127.7 (3) |
C13—C14—C15 | 119.9 (4) | N28—C29—C210 | 122.8 (4) |
C13—C14—H14 | 120.1 | N28—C29—H29 | 118.6 |
C15—C14—H14 | 120.1 | C210—C29—H29 | 118.6 |
C14—C15—C16 | 119.6 (4) | C211—C210—C29 | 118.7 (4) |
C14—C15—H15 | 120.2 | C211—C210—H210 | 120.6 |
C16—C15—H15 | 120.2 | C29—C210—H210 | 120.6 |
N11—C16—C15 | 120.3 (4) | C210—C211—C212 | 119.6 (4) |
N11—C16—C17 | 115.0 (3) | C210—C211—H211 | 120.2 |
C15—C16—C17 | 124.7 (4) | C212—C211—H211 | 120.2 |
N18—C17—C112 | 121.6 (4) | C211—C212—C27 | 119.3 (4) |
N18—C17—C16 | 115.3 (3) | C211—C212—H212 | 120.4 |
C112—C17—C16 | 123.1 (4) | C27—C212—H212 | 120.4 |
C19—N18—C17 | 117.8 (3) | O3—N1—O2 | 124.1 (4) |
C19—N18—Cu1 | 129.3 (3) | O3—N1—O1 | 118.3 (4) |
C17—N18—Cu1 | 112.9 (3) | O2—N1—O1 | 117.6 (4) |
N18—C19—C110 | 123.8 (4) | N1—O1—Cu1 | 110.7 (3) |
N18—C19—H19 | 118.1 | N1—O3—Cu1i | 159.5 (3) |
C110—C19—H19 | 118.1 | F4—P1—F1 | 92.6 (2) |
C111—C110—C19 | 117.6 (4) | F4—P1—F2 | 179.0 (2) |
C111—C110—H110 | 121.2 | F1—P1—F2 | 88.29 (17) |
C19—C110—H110 | 121.2 | F4—P1—F5 | 90.74 (15) |
C110—C111—C112 | 119.6 (4) | F1—P1—F5 | 90.63 (17) |
C110—C111—H111 | 120.2 | F2—P1—F5 | 89.75 (14) |
C112—C111—H111 | 120.2 | F4—P1—F3 | 90.0 (2) |
C111—C112—C17 | 119.6 (4) | F1—P1—F3 | 177.31 (19) |
C111—C112—H112 | 120.2 | F2—P1—F3 | 89.12 (18) |
C17—C112—H112 | 120.2 | F5—P1—F3 | 88.61 (16) |
C22—N21—C26 | 118.7 (3) | F4—P1—F6 | 90.43 (15) |
C22—N21—Cu1 | 126.4 (3) | F1—P1—F6 | 90.11 (18) |
C26—N21—Cu1 | 114.5 (2) | F2—P1—F6 | 89.06 (15) |
N21—C22—C23 | 123.0 (3) | F5—P1—F6 | 178.58 (18) |
N21—C22—H22 | 118.5 | F3—P1—F6 | 90.59 (18) |
Symmetry code: (i) x−1, y, z. |
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