Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804024249/rz6006sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804024249/rz6006Isup2.hkl |
CCDC reference: 255404
Data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 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); software used to prepare material for publication: WinGX (Farrugia, 1999).
[Cu(NO2)2(C15H26N2)] | Dx = 1.519 Mg m−3 |
Mr = 389.94 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P41212 | Cell parameters from 22 reflections |
Hall symbol: P 4abw 2nw | θ = 11.4–14.1° |
a = 8.2446 (5) Å | µ = 1.31 mm−1 |
c = 25.088 (4) Å | T = 293 K |
V = 1705.3 (3) Å3 | Block, dark green |
Z = 4 | 0.30 × 0.23 × 0.23 mm |
F(000) = 820 |
Enraf–Nonius CAD-4 diffractometer | 1445 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.061 |
Graphite monochromator | θmax = 27.5°, θmin = 2.6° |
non–profiled ω/2θ scans | h = −10→10 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→10 |
Tmin = 0.622, Tmax = 0.730 | l = 0→32 |
4231 measured reflections | 3 standard reflections every 400 reflections |
1956 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.083 | w = 1/[σ2(Fo2) + (0.0297P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
1956 reflections | Δρmax = 0.44 e Å−3 |
120 parameters | Δρmin = −0.23 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 737 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (2) |
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 | Occ. (<1) | |
Cu | 0.22073 (5) | 0.22073 (5) | 0.0000 | 0.03224 (16) | |
N1 | −0.0235 (3) | 0.2150 (3) | 0.01373 (9) | 0.0301 (6) | |
N2 | 0.4899 (5) | 0.2616 (5) | 0.05914 (17) | 0.0661 (11) | |
O1 | 0.4632 (3) | 0.2331 (4) | 0.01043 (11) | 0.0618 (8) | |
O2 | 0.360 (5) | 0.247 (8) | 0.0882 (13) | 0.072 (6) | 0.5 (2) |
O2A | 0.375 (6) | 0.278 (11) | 0.0838 (18) | 0.075 (9) | 0.5 (2) |
C2 | −0.0917 (5) | 0.3801 (4) | 0.02421 (13) | 0.0403 (9) | |
H2A | −0.2092 | 0.3735 | 0.0249 | 0.048* | |
H2B | −0.0611 | 0.4521 | −0.0047 | 0.048* | |
C3 | −0.0326 (5) | 0.4506 (4) | 0.07654 (14) | 0.0479 (10) | |
H3A | 0.0839 | 0.4666 | 0.0748 | 0.058* | |
H3B | −0.0829 | 0.5555 | 0.0823 | 0.058* | |
C4 | −0.0726 (5) | 0.3395 (5) | 0.12285 (14) | 0.0497 (10) | |
H4A | −0.1892 | 0.3354 | 0.1279 | 0.060* | |
H4B | −0.0242 | 0.3817 | 0.1552 | 0.060* | |
C5 | −0.0085 (5) | 0.1698 (4) | 0.11210 (13) | 0.0421 (9) | |
H5A | −0.0423 | 0.0977 | 0.1406 | 0.051* | |
H5B | 0.1092 | 0.1720 | 0.1115 | 0.051* | |
C6 | −0.0712 (4) | 0.1056 (4) | 0.05904 (12) | 0.0329 (8) | |
H6 | −0.1898 | 0.1089 | 0.0611 | 0.039* | |
C8 | −0.1002 (4) | 0.1528 (4) | −0.03672 (13) | 0.0365 (9) | |
H8A | −0.0590 | 0.2152 | −0.0666 | 0.044* | |
H8B | −0.2163 | 0.1707 | −0.0348 | 0.044* | |
C7 | −0.0696 (4) | −0.0255 (4) | −0.04733 (13) | 0.0361 (8) | |
H7 | −0.1348 | −0.0567 | −0.0783 | 0.043* | |
C9 | −0.1272 (4) | −0.1272 (4) | 0.0000 | 0.0425 (12) | |
H9 | −0.2418 | −0.1095 | 0.0066 | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu | 0.03328 (19) | 0.03328 (19) | 0.0302 (3) | −0.0058 (2) | 0.00386 (19) | −0.00386 (19) |
N1 | 0.0341 (15) | 0.0299 (13) | 0.0264 (13) | 0.0022 (13) | −0.0009 (10) | −0.0004 (13) |
N2 | 0.044 (2) | 0.081 (3) | 0.073 (3) | −0.008 (2) | −0.005 (2) | −0.019 (2) |
O1 | 0.0424 (16) | 0.083 (2) | 0.0602 (18) | −0.0096 (14) | 0.0009 (13) | −0.0262 (18) |
O2 | 0.056 (9) | 0.098 (14) | 0.061 (10) | −0.013 (12) | 0.015 (9) | 0.009 (10) |
O2A | 0.059 (8) | 0.12 (2) | 0.042 (9) | −0.037 (13) | −0.006 (8) | −0.012 (11) |
C2 | 0.048 (2) | 0.033 (2) | 0.041 (2) | 0.0057 (17) | 0.0031 (17) | −0.0038 (16) |
C3 | 0.057 (3) | 0.042 (2) | 0.045 (2) | 0.0044 (18) | 0.0098 (19) | −0.0112 (18) |
C4 | 0.054 (3) | 0.062 (3) | 0.0335 (19) | 0.0007 (19) | 0.0068 (19) | −0.0166 (18) |
C5 | 0.045 (2) | 0.054 (3) | 0.0275 (17) | 0.0003 (17) | 0.0052 (16) | 0.0014 (16) |
C6 | 0.0271 (18) | 0.044 (2) | 0.0272 (16) | −0.0026 (15) | 0.0035 (14) | 0.0013 (15) |
C8 | 0.035 (2) | 0.045 (2) | 0.0291 (17) | 0.0063 (17) | −0.0065 (15) | −0.0014 (15) |
C7 | 0.037 (2) | 0.038 (2) | 0.0338 (17) | −0.0040 (16) | −0.0063 (14) | −0.0048 (15) |
C9 | 0.0396 (17) | 0.0396 (17) | 0.048 (3) | −0.012 (2) | 0.004 (2) | −0.004 (2) |
Cu—N1 | 2.043 (3) | C3—H3B | 0.9700 |
Cu—N1i | 2.043 (3) | C4—C5 | 1.520 (5) |
Cu—O1 | 2.019 (3) | C4—H4A | 0.9700 |
Cu—O1i | 2.019 (3) | C4—H4B | 0.9700 |
Cu—O2 | 2.50 (3) | C5—C6 | 1.523 (4) |
Cu—O2i | 2.50 (3) | C5—H5A | 0.9700 |
N1—C2 | 1.496 (4) | C5—H5B | 0.9700 |
N1—C6 | 1.503 (4) | C6—C7i | 1.521 (4) |
N1—C8 | 1.505 (4) | C6—H6 | 0.9800 |
N2—O2A | 1.14 (5) | C8—C7 | 1.515 (4) |
N2—O1 | 1.264 (4) | C8—H8A | 0.9700 |
N2—O2 | 1.30 (5) | C8—H8B | 0.9700 |
C2—C3 | 1.517 (5) | C7—C6i | 1.521 (4) |
C2—H2A | 0.9700 | C7—C9 | 1.529 (4) |
C2—H2B | 0.9700 | C7—H7 | 0.9800 |
C3—C4 | 1.516 (5) | C9—C7i | 1.529 (4) |
C3—H3A | 0.9700 | C9—H9 | 0.9700 |
N1—Cu—N1i | 89.01 (16) | C2—C3—H3B | 109.4 |
N1—Cu—O1 | 162.78 (9) | H3A—C3—H3B | 108.0 |
N1—Cu—O1i | 95.43 (12) | C3—C4—C5 | 110.1 (3) |
N1—Cu—O2 | 107.8 (11) | C3—C4—H4A | 109.6 |
N1—Cu—O2i | 104.2 (14) | C5—C4—H4A | 109.6 |
O1—Cu—N1i | 95.43 (12) | C3—C4—H4B | 109.6 |
O1—Cu—O1i | 85.23 (18) | C5—C4—H4B | 109.6 |
O1—Cu—O2 | 55.0 (11) | H4A—C4—H4B | 108.1 |
O1—Cu—O2i | 90.3 (15) | C4—C5—C6 | 110.9 (3) |
O2—Cu—N1i | 104.2 (14) | C4—C5—H5A | 109.5 |
O2—Cu—O1i | 90.3 (15) | C6—C5—H5A | 109.5 |
O2—Cu—O2i | 135 (3) | C4—C5—H5B | 109.5 |
N1i—Cu—O1i | 162.78 (9) | C6—C5—H5B | 109.5 |
N1i—Cu—O2i | 107.8 (11) | H5A—C5—H5B | 108.0 |
O1i—Cu—O2i | 55.0 (11) | N1—C6—C7i | 111.0 (2) |
C2—N1—C6 | 108.3 (2) | N1—C6—C5 | 111.3 (3) |
C2—N1—C8 | 107.4 (2) | C7i—C6—C5 | 114.5 (3) |
C6—N1—C8 | 108.8 (3) | N1—C6—H6 | 106.5 |
C2—N1—Cu | 112.3 (2) | C7i—C6—H6 | 106.5 |
C6—N1—Cu | 113.52 (18) | C5—C6—H6 | 106.5 |
C8—N1—Cu | 106.28 (19) | N1—C8—C7 | 114.1 (3) |
O2A—N2—O1 | 113.9 (11) | N1—C8—H8A | 108.7 |
O2A—N2—O2 | 12 (5) | C7—C8—H8A | 108.7 |
O1—N2—O2 | 112.4 (13) | N1—C8—H8B | 108.7 |
N2—O1—Cu | 107.9 (2) | C7—C8—H8B | 108.7 |
N2—O2—Cu | 83.7 (14) | H8A—C8—H8B | 107.6 |
N1—C2—C3 | 112.3 (3) | C8—C7—C6i | 115.6 (3) |
N1—C2—H2A | 109.1 | C8—C7—C9 | 110.1 (2) |
C3—C2—H2A | 109.1 | C6i—C7—C9 | 108.0 (2) |
N1—C2—H2B | 109.1 | C8—C7—H7 | 107.6 |
C3—C2—H2B | 109.1 | C6i—C7—H7 | 107.6 |
H2A—C2—H2B | 107.9 | C9—C7—H7 | 107.6 |
C4—C3—C2 | 111.2 (3) | C7i—C9—C7 | 105.2 (3) |
C4—C3—H3A | 109.4 | C7i—C9—H9 | 110.7 |
C2—C3—H3A | 109.4 | C7—C9—H9 | 110.7 |
C4—C3—H3B | 109.4 |
Symmetry code: (i) y, x, −z. |