metal-organic compounds
In both of the two independent molecules of the title compound, [Cu(C9H7NO3)(C5H5N)(H2O)], the copper atom is in a square-pyramidal coordination with the apical site occupied by water. The two molecules are related by a non-crystallographic center of inversion. Hydrogen bonds link symmetry-equivalent molecules into zigzag chains that run along the a axis of the orthorhombic unit cell.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805033647/cf6465sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805033647/cf6465Isup2.hkl |
CCDC reference: 289688
Computing details top
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Crystal data top
[Cu(C9H7NO3)(C5H5N)(H2O)] | F(000) = 1384 |
Mr = 337.81 | Dx = 1.584 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 4366 reflections |
a = 9.6232 (5) Å | θ = 2.8–24.9° |
b = 10.8138 (6) Å | µ = 1.56 mm−1 |
c = 27.219 (2) Å | T = 295 K |
V = 2832.4 (3) Å3 | Prism, deep blue |
Z = 8 | 0.30 × 0.20 × 0.08 mm |
Data collection top
Bruker APEX area-detector diffractometer | 6066 independent reflections |
Radiation source: fine-focus sealed tube | 4788 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
φ and ω scans | θmax = 27.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→11 |
Tmin = 0.660, Tmax = 0.885 | k = −13→12 |
16774 measured reflections | l = −30→35 |
Refinement top
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)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.137 | w = 1/[σ2(Fo2) + (0.0839P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
6066 reflections | Δρmax = 0.48 e Å−3 |
396 parameters | Δρmin = −0.40 e Å−3 |
7 restraints | Absolute structure: Flack (1983), 3294 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.48 (2) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.96362 (6) | 0.33174 (5) | 0.50000 (2) | 0.03827 (16) | |
Cu2 | 0.78831 (6) | 0.16624 (5) | 0.69831 (2) | 0.03743 (16) | |
O1 | 1.1050 (5) | 0.3177 (3) | 0.4503 (2) | 0.047 (1) | |
O2 | 0.8113 (4) | 0.3606 (4) | 0.5474 (2) | 0.049 (1) | |
O3 | 0.7052 (6) | 0.5056 (4) | 0.5916 (3) | 0.053 (2) | |
O4 | 0.6466 (4) | 0.1788 (3) | 0.7471 (2) | 0.048 (1) | |
O5 | 0.9419 (4) | 0.1388 (4) | 0.6508 (2) | 0.045 (1) | |
O6 | 1.0504 (6) | −0.0049 (4) | 0.6079 (3) | 0.053 (2) | |
O1w | 1.1087 (4) | 0.2638 (4) | 0.5662 (2) | 0.050 (1) | |
O2w | 0.6441 (4) | 0.2365 (4) | 0.6323 (2) | 0.050 (1) | |
N1 | 0.9832 (7) | 0.5108 (4) | 0.5031 (4) | 0.042 (2) | |
N2 | 0.9008 (5) | 0.1562 (4) | 0.4884 (2) | 0.038 (1) | |
N3 | 0.7749 (6) | −0.0121 (4) | 0.6960 (4) | 0.037 (1) | |
N4 | 0.8516 (5) | 0.3414 (4) | 0.7100 (2) | 0.038 (1) | |
C1 | 1.0573 (6) | 0.5775 (5) | 0.4751 (2) | 0.046 (1) | |
C2 | 1.1508 (6) | 0.5333 (7) | 0.4382 (2) | 0.043 (1) | |
C3 | 1.2279 (9) | 0.6205 (7) | 0.4117 (3) | 0.056 (2) | |
C4 | 1.3260 (9) | 0.586 (1) | 0.3781 (3) | 0.071 (3) | |
C5 | 1.3443 (8) | 0.464 (1) | 0.3690 (3) | 0.061 (2) | |
C6 | 1.2699 (8) | 0.3740 (7) | 0.3923 (3) | 0.050 (2) | |
C7 | 1.1713 (6) | 0.4054 (6) | 0.4281 (2) | 0.040 (1) | |
C8 | 0.8907 (6) | 0.5682 (5) | 0.5401 (2) | 0.049 (1) | |
C9 | 0.7954 (6) | 0.4741 (6) | 0.5607 (3) | 0.039 (1) | |
C10 | 0.9336 (7) | 0.0942 (6) | 0.4482 (3) | 0.057 (2) | |
C11 | 0.887 (1) | −0.0236 (8) | 0.4389 (4) | 0.074 (3) | |
C12 | 0.8052 (7) | −0.0817 (7) | 0.4733 (3) | 0.066 (2) | |
C13 | 0.772 (1) | −0.0191 (7) | 0.5152 (4) | 0.059 (2) | |
C14 | 0.8205 (7) | 0.0978 (5) | 0.5211 (2) | 0.056 (2) | |
C15 | 0.5794 (6) | 0.0866 (6) | 0.7699 (2) | 0.040 (1) | |
C16 | 0.4810 (8) | 0.1167 (7) | 0.8055 (3) | 0.050 (2) | |
C17 | 0.4067 (9) | 0.0272 (9) | 0.8304 (3) | 0.062 (2) | |
C18 | 0.4318 (9) | −0.0973 (7) | 0.8204 (3) | 0.061 (2) | |
C19 | 0.5283 (8) | −0.1283 (7) | 0.7862 (3) | 0.053 (2) | |
C20 | 0.6011 (6) | −0.0373 (6) | 0.7601 (2) | 0.039 (1) | |
C21 | 0.7001 (5) | −0.0823 (5) | 0.7232 (2) | 0.041 (1) | |
C22 | 0.8619 (6) | −0.0682 (5) | 0.6589 (2) | 0.047 (1) | |
C23 | 0.9621 (6) | 0.0275 (6) | 0.6363 (3) | 0.044 (2) | |
C24 | 0.8190 (7) | 0.4023 (6) | 0.7515 (3) | 0.056 (2) | |
C25 | 0.870 (1) | 0.5183 (7) | 0.7612 (4) | 0.064 (2) | |
C26 | 0.9474 (7) | 0.5788 (6) | 0.7270 (3) | 0.062 (2) | |
C27 | 0.979 (1) | 0.5189 (7) | 0.6855 (5) | 0.070 (3) | |
C28 | 0.9286 (7) | 0.4000 (6) | 0.6773 (2) | 0.054 (2) | |
H1w1 | 1.120 (6) | 0.333 (2) | 0.581 (2) | 0.04 (2)* | |
H1w2 | 1.108 (8) | 0.206 (3) | 0.587 (2) | 0.07 (2)* | |
H2w1 | 0.635 (7) | 0.169 (3) | 0.617 (2) | 0.05 (2)* | |
H2w2 | 0.661 (6) | 0.294 (3) | 0.612 (2) | 0.05 (2)* | |
H1 | 1.0502 | 0.6627 | 0.4789 | 0.056* | |
H3 | 1.2119 | 0.7042 | 0.4171 | 0.067* | |
H4 | 1.3791 | 0.6451 | 0.3618 | 0.086* | |
H5 | 1.4104 | 0.4402 | 0.3459 | 0.074* | |
H6 | 1.2845 | 0.2913 | 0.3844 | 0.060* | |
H8a | 0.9461 | 0.6040 | 0.5663 | 0.058* | |
H8b | 0.8372 | 0.6340 | 0.5250 | 0.058* | |
H10 | 0.9907 | 0.1321 | 0.4251 | 0.069* | |
H11 | 0.9112 | −0.0636 | 0.4099 | 0.089* | |
H12 | 0.7733 | −0.1618 | 0.4680 | 0.080* | |
H13 | 0.7163 | −0.0557 | 0.5392 | 0.071* | |
H14 | 0.7966 | 0.1399 | 0.5497 | 0.067* | |
H16 | 0.4649 | 0.1996 | 0.8127 | 0.060* | |
H17 | 0.3406 | 0.0498 | 0.8537 | 0.074* | |
H18 | 0.3828 | −0.1586 | 0.8370 | 0.073* | |
H19 | 0.5465 | −0.2113 | 0.7800 | 0.063* | |
H21 | 0.7093 | −0.1674 | 0.7194 | 0.049* | |
H22a | 0.8039 | −0.1030 | 0.6333 | 0.056* | |
H22b | 0.9151 | −0.1350 | 0.6735 | 0.056* | |
H24 | 0.7603 | 0.3648 | 0.7742 | 0.067* | |
H25 | 0.8512 | 0.5556 | 0.7913 | 0.077* | |
H26 | 0.9777 | 0.6594 | 0.7324 | 0.074* | |
H27 | 1.0342 | 0.5570 | 0.6619 | 0.084* | |
H28 | 0.9500 | 0.3605 | 0.6479 | 0.065* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0397 (3) | 0.0305 (3) | 0.0447 (3) | −0.0010 (2) | 0.0079 (3) | 0.0044 (3) |
Cu2 | 0.0381 (3) | 0.0296 (3) | 0.0445 (3) | −0.0010 (2) | 0.0069 (2) | 0.0026 (3) |
O1 | 0.048 (2) | 0.039 (2) | 0.054 (3) | 0.005 (2) | 0.018 (2) | 0.009 (2) |
O2 | 0.051 (2) | 0.037 (2) | 0.058 (3) | 0.004 (2) | 0.014 (2) | 0.006 (2) |
O3 | 0.049 (4) | 0.047 (3) | 0.064 (5) | 0.008 (2) | 0.004 (3) | 0.000 (2) |
O4 | 0.050 (2) | 0.036 (2) | 0.057 (3) | 0.000 (2) | 0.013 (2) | 0.008 (2) |
O5 | 0.049 (2) | 0.032 (2) | 0.055 (3) | −0.002 (2) | 0.017 (2) | 0.001 (2) |
O6 | 0.065 (5) | 0.052 (3) | 0.041 (4) | 0.007 (2) | 0.021 (3) | 0.002 (2) |
O1w | 0.050 (2) | 0.043 (2) | 0.056 (2) | −0.005 (2) | 0.004 (2) | 0.009 (2) |
O2w | 0.050 (2) | 0.044 (2) | 0.057 (3) | −0.007 (2) | 0.004 (2) | 0.005 (2) |
N1 | 0.045 (3) | 0.036 (2) | 0.045 (4) | −0.004 (2) | 0.004 (3) | 0.000 (2) |
N2 | 0.038 (2) | 0.038 (2) | 0.038 (3) | −0.003 (2) | 0.005 (2) | 0.003 (2) |
N3 | 0.036 (3) | 0.030 (2) | 0.044 (4) | 0.000 (2) | 0.000 (3) | 0.008 (2) |
N4 | 0.040 (2) | 0.035 (2) | 0.039 (2) | −0.003 (2) | 0.004 (2) | 0.002 (2) |
C1 | 0.050 (3) | 0.035 (3) | 0.054 (3) | −0.006 (2) | −0.012 (3) | 0.012 (2) |
C2 | 0.035 (3) | 0.054 (3) | 0.040 (4) | −0.011 (3) | −0.003 (2) | 0.016 (4) |
C3 | 0.055 (5) | 0.059 (4) | 0.054 (5) | −0.024 (3) | −0.014 (3) | 0.017 (3) |
C4 | 0.058 (5) | 0.106 (7) | 0.050 (5) | −0.046 (5) | 0.002 (4) | 0.024 (5) |
C5 | 0.048 (4) | 0.097 (6) | 0.039 (4) | −0.010 (5) | 0.003 (3) | 0.013 (5) |
C6 | 0.050 (4) | 0.065 (4) | 0.033 (4) | −0.003 (3) | 0.005 (3) | 0.007 (3) |
C7 | 0.034 (3) | 0.047 (4) | 0.041 (4) | −0.008 (3) | −0.006 (2) | 0.008 (3) |
C8 | 0.046 (3) | 0.039 (3) | 0.061 (4) | −0.003 (2) | 0.013 (3) | −0.006 (3) |
C9 | 0.036 (3) | 0.046 (3) | 0.034 (3) | 0.014 (3) | −0.001 (2) | −0.002 (3) |
C10 | 0.066 (4) | 0.055 (4) | 0.051 (4) | −0.012 (3) | 0.020 (3) | −0.012 (3) |
C11 | 0.092 (7) | 0.060 (4) | 0.070 (7) | −0.019 (5) | 0.030 (6) | −0.029 (5) |
C12 | 0.079 (5) | 0.051 (4) | 0.069 (5) | −0.028 (3) | 0.009 (4) | −0.013 (3) |
C13 | 0.076 (6) | 0.055 (4) | 0.048 (5) | −0.024 (4) | 0.014 (4) | 0.007 (4) |
C14 | 0.088 (5) | 0.037 (3) | 0.042 (3) | −0.009 (3) | 0.024 (3) | −0.004 (3) |
C15 | 0.024 (3) | 0.056 (4) | 0.040 (4) | 0.000 (3) | 0.000 (2) | 0.011 (3) |
C16 | 0.049 (4) | 0.058 (4) | 0.042 (4) | −0.001 (3) | 0.002 (3) | −0.001 (3) |
C17 | 0.047 (4) | 0.098 (6) | 0.041 (4) | −0.027 (5) | 0.006 (3) | −0.001 (5) |
C18 | 0.071 (5) | 0.062 (5) | 0.050 (5) | −0.031 (4) | 0.009 (4) | 0.012 (4) |
C19 | 0.065 (5) | 0.049 (3) | 0.044 (4) | −0.019 (3) | 0.001 (3) | 0.005 (3) |
C20 | 0.037 (3) | 0.042 (3) | 0.039 (3) | −0.009 (3) | −0.003 (2) | 0.004 (3) |
C21 | 0.037 (3) | 0.036 (2) | 0.050 (3) | −0.004 (2) | −0.001 (2) | 0.004 (2) |
C22 | 0.047 (3) | 0.035 (3) | 0.057 (4) | 0.000 (2) | 0.003 (3) | −0.005 (3) |
C23 | 0.038 (4) | 0.041 (3) | 0.052 (4) | −0.001 (3) | −0.001 (3) | 0.017 (4) |
C24 | 0.071 (4) | 0.046 (4) | 0.052 (4) | −0.016 (3) | 0.011 (3) | −0.006 (3) |
C25 | 0.072 (5) | 0.064 (4) | 0.057 (5) | −0.016 (4) | 0.015 (4) | −0.023 (4) |
C26 | 0.071 (5) | 0.045 (4) | 0.070 (5) | −0.020 (3) | 0.008 (3) | −0.015 (3) |
C27 | 0.085 (6) | 0.044 (4) | 0.082 (8) | −0.025 (4) | 0.032 (5) | −0.006 (4) |
C28 | 0.070 (4) | 0.046 (4) | 0.047 (4) | −0.014 (3) | 0.010 (3) | −0.001 (3) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.924 (4) | C16—C17 | 1.382 (10) |
Cu1—O2 | 1.977 (4) | C17—C18 | 1.395 (12) |
Cu1—O1w | 2.396 (4) | C18—C19 | 1.357 (11) |
Cu1—N1 | 1.948 (4) | C19—C20 | 1.402 (9) |
Cu1—N2 | 2.017 (4) | C20—C21 | 1.466 (8) |
Cu2—O4 | 1.908 (4) | C22—C23 | 1.544 (9) |
Cu2—O5 | 1.987 (4) | C24—C25 | 1.372 (9) |
Cu2—O2w | 2.393 (4) | C25—C26 | 1.360 (12) |
Cu2—N3 | 1.934 (4) | C26—C27 | 1.338 (13) |
Cu2—N4 | 2.015 (4) | C27—C28 | 1.392 (9) |
O1—C7 | 1.293 (7) | O1w—H1w1 | 0.85 (1) |
O2—C9 | 1.289 (8) | O1w—H1w2 | 0.85 (1) |
O3—C9 | 1.255 (9) | O2w—H2w1 | 0.85 (1) |
O4—C15 | 1.340 (7) | O2w—H2w2 | 0.85 (1) |
O5—C23 | 1.281 (9) | C1—H1 | 0.93 |
O6—C23 | 1.200 (9) | C3—H3 | 0.93 |
N1—C1 | 1.27 (1) | C4—H4 | 0.93 |
N1—C8 | 1.48 (1) | C5—H5 | 0.93 |
N2—C10 | 1.324 (8) | C6—H6 | 0.93 |
N2—C14 | 1.336 (7) | C8—H8a | 0.97 |
N3—C21 | 1.282 (9) | C8—H8b | 0.97 |
N3—C22 | 1.45 (1) | C10—H10 | 0.93 |
N4—C28 | 1.321 (7) | C11—H11 | 0.93 |
N4—C24 | 1.343 (8) | C12—H12 | 0.93 |
C1—C2 | 1.43 (1) | C13—H13 | 0.93 |
C2—C3 | 1.400 (9) | C14—H14 | 0.93 |
C2—C7 | 1.424 (9) | C16—H16 | 0.93 |
C3—C4 | 1.37 (1) | C17—H17 | 0.93 |
C4—C5 | 1.36 (1) | C18—H18 | 0.93 |
C5—C6 | 1.36 (1) | C19—H19 | 0.93 |
C6—C7 | 1.402 (9) | C21—H21 | 0.93 |
C8—C9 | 1.480 (9) | C22—H22a | 0.97 |
C10—C11 | 1.372 (9) | C22—H22b | 0.97 |
C11—C12 | 1.38 (1) | C24—H24 | 0.93 |
C12—C13 | 1.37 (1) | C25—H25 | 0.93 |
C13—C14 | 1.359 (9) | C26—H26 | 0.93 |
C15—C20 | 1.382 (9) | C27—H27 | 0.93 |
C15—C16 | 1.393 (9) | C28—H28 | 0.93 |
O1—Cu1—O1w | 95.3 (2) | N3—C21—C20 | 124.3 (6) |
O1—Cu1—O2 | 174.3 (2) | N3—C22—C23 | 111.0 (5) |
O1—Cu1—N2 | 91.6 (2) | O6—C23—O5 | 125.4 (6) |
O1—Cu1—N1 | 92.3 (3) | O6—C23—C22 | 120.2 (6) |
O2—Cu1—O1w | 89.4 (2) | O5—C23—C22 | 114.4 (6) |
O2—Cu1—N2 | 91.6 (2) | N4—C24—C25 | 121.8 (7) |
O2—Cu1—N1 | 83.5 (3) | C26—C25—C24 | 120.3 (9) |
O1w—Cu1—N1 | 102.5 (3) | C27—C26—C25 | 117.9 (7) |
O1w—Cu1—N2 | 90.2 (2) | C26—C27—C28 | 120.3 (8) |
N1—Cu1—N2 | 166.3 (3) | N4—C28—C27 | 121.9 (7) |
O4—Cu2—O5 | 174.6 (2) | Cu1—O1w—H1w1 | 99 (4) |
O4—Cu2—N3 | 92.6 (3) | Cu1—O1w—H1w2 | 137 (5) |
O4—Cu2—N4 | 92.2 (2) | H1w1—O1w—H1w2 | 109 (2) |
O4—Cu2—O2w | 94.9 (2) | Cu2—O2w—H2w1 | 99 (4) |
O5—Cu2—O2w | 89.5 (2) | Cu2—O2w—H2w2 | 128 (4) |
O5—Cu2—N3 | 83.1 (3) | H2w1—O2w—H2w2 | 109 (2) |
O5—Cu2—N4 | 91.1 (2) | N1—C1—H1 | 117.1 |
O2w—Cu2—N3 | 104.7 (3) | C2—C1—H1 | 117.1 |
O2w—Cu2—N4 | 89.7 (2) | C4—C3—H3 | 119.1 |
N3—Cu2—N4 | 164.3 (2) | C2—C3—H3 | 119.1 |
C7—O1—Cu1 | 128.3 (4) | C5—C4—H4 | 120.7 |
C9—O2—Cu1 | 115.0 (4) | C3—C4—H4 | 120.7 |
C15—O4—Cu2 | 127.9 (4) | C4—C5—H5 | 118.6 |
C23—O5—Cu2 | 117.0 (4) | C6—C5—H5 | 118.6 |
C1—N1—C8 | 120.6 (5) | C5—C6—H6 | 119.8 |
C1—N1—Cu1 | 126.4 (6) | C7—C6—H6 | 119.8 |
C8—N1—Cu1 | 112.8 (5) | C9—C8—H8a | 109.7 |
C10—N2—C14 | 116.7 (5) | N1—C8—H8a | 109.7 |
C10—N2—Cu1 | 122.3 (4) | C9—C8—H8b | 109.7 |
C14—N2—Cu1 | 121.0 (4) | N1—C8—H8b | 109.7 |
C21—N3—C22 | 118.7 (4) | H8a—C8—H8b | 108.2 |
C21—N3—Cu2 | 127.6 (6) | N2—C10—H10 | 118.5 |
C22—N3—Cu2 | 113.8 (5) | C11—C10—H10 | 118.5 |
C28—N4—C24 | 117.6 (5) | C10—C11—H11 | 120.5 |
C28—N4—Cu2 | 120.8 (4) | C12—C11—H11 | 120.5 |
C24—N4—Cu2 | 121.5 (4) | C13—C12—H12 | 120.7 |
N1—C1—C2 | 125.9 (6) | C11—C12—H12 | 120.7 |
C3—C2—C7 | 118.8 (7) | C14—C13—H13 | 120.7 |
C3—C2—C1 | 118.1 (7) | C12—C13—H13 | 120.7 |
C7—C2—C1 | 123.2 (6) | N2—C14—H14 | 117.9 |
C4—C3—C2 | 121.9 (8) | C13—C14—H14 | 117.9 |
C5—C4—C3 | 118.5 (7) | C17—C16—H16 | 119.0 |
C4—C5—C6 | 122.8 (8) | C15—C16—H16 | 119.0 |
C5—C6—C7 | 120.4 (7) | C16—C17—H17 | 120.3 |
O1—C7—C6 | 118.8 (6) | C18—C17—H17 | 120.3 |
O1—C7—C2 | 123.6 (6) | C19—C18—H18 | 120.3 |
C6—C7—C2 | 117.6 (6) | C17—C18—H18 | 120.3 |
C9—C8—N1 | 110.0 (5) | C18—C19—H19 | 119.4 |
O3—C9—O2 | 122.0 (6) | C20—C19—H19 | 119.4 |
O3—C9—C8 | 119.7 (6) | N3—C21—H21 | 117.9 |
O2—C9—C8 | 118.3 (6) | C20—C21—H21 | 117.9 |
N2—C10—C11 | 123.0 (7) | N3—C22—H22a | 109.4 |
C10—C11—C12 | 119.1 (8) | C23—C22—H22a | 109.4 |
C13—C12—C11 | 118.5 (6) | N3—C22—H22b | 109.4 |
C14—C13—C12 | 118.5 (7) | C23—C22—H22b | 109.4 |
N2—C14—C13 | 124.2 (6) | H22a—C22—H22b | 108.0 |
O4—C15—C20 | 124.0 (6) | N4—C24—H24 | 119.1 |
O4—C15—C16 | 118.4 (6) | C25—C24—H24 | 119.1 |
C20—C15—C16 | 117.6 (6) | C26—C25—H25 | 119.9 |
C17—C16—C15 | 122.0 (7) | C24—C25—H25 | 119.9 |
C16—C17—C18 | 119.4 (8) | C27—C26—H26 | 121.0 |
C19—C18—C17 | 119.4 (7) | C25—C26—H26 | 121.0 |
C18—C19—C20 | 121.1 (7) | C26—C27—H27 | 119.8 |
C15—C20—C19 | 120.5 (6) | C28—C27—H27 | 119.8 |
C15—C20—C21 | 123.5 (6) | N4—C28—H28 | 119.0 |
C19—C20—C21 | 116.0 (6) | C27—C28—H28 | 119.0 |
N1—Cu1—O1—C7 | −4.5 (6) | Cu1—O1—C7—C6 | −179.2 (5) |
N2—Cu1—O1—C7 | 162.4 (5) | Cu1—O1—C7—C2 | 1.3 (9) |
O1w—Cu1—O1—C7 | −107.3 (5) | C5—C6—C7—O1 | −178.3 (7) |
N1—Cu1—O2—C9 | −2.9 (5) | C5—C6—C7—C2 | 1 (1) |
N2—Cu1—O2—C9 | −170.1 (5) | C3—C2—C7—O1 | −179.7 (6) |
O1w—Cu1—O2—C9 | 99.7 (4) | C1—C2—C7—O1 | 1.9 (9) |
N3—Cu2—O4—C15 | 3.6 (6) | C3—C2—C7—C6 | 0.8 (9) |
N4—Cu2—O4—C15 | −161.4 (5) | C1—C2—C7—C6 | −177.6 (6) |
O2w—Cu2—O4—C15 | 108.6 (5) | C1—N1—C8—C9 | 168.4 (7) |
N3—Cu2—O5—C23 | 4.6 (5) | Cu1—N1—C8—C9 | −6.9 (8) |
N4—Cu2—O5—C23 | 170.0 (5) | Cu1—O2—C9—O3 | −178.2 (6) |
O2w—Cu2—O5—C23 | −100.3 (5) | Cu1—O2—C9—C8 | −0.4 (8) |
O1—Cu1—N1—C1 | 6.6 (8) | N1—C8—C9—O3 | −177.4 (7) |
O2—Cu1—N1—C1 | −169.5 (8) | N1—C8—C9—O2 | 4.8 (9) |
N2—Cu1—N1—C1 | −100 (1) | C14—N2—C10—C11 | 1 (1) |
O1w—Cu1—N1—C1 | 102.5 (7) | Cu1—N2—C10—C11 | −177.5 (7) |
O1—Cu1—N1—C8 | −178.5 (6) | N2—C10—C11—C12 | −1 (2) |
O2—Cu1—N1—C8 | 5.5 (6) | C10—C11—C12—C13 | 1 (2) |
N2—Cu1—N1—C8 | 75 (2) | C11—C12—C13—C14 | 0 (1) |
O1w—Cu1—N1—C8 | −82.5 (6) | C10—N2—C14—C13 | 0 (1) |
O1—Cu1—N2—C10 | −17.4 (5) | Cu1—N2—C14—C13 | 178.3 (6) |
N1—Cu1—N2—C10 | 89 (2) | C12—C13—C14—N2 | 0 (1) |
O2—Cu1—N2—C10 | 157.8 (5) | Cu2—O4—C15—C20 | −1.9 (8) |
O1w—Cu1—N2—C10 | −112.7 (5) | Cu2—O4—C15—C16 | 178.5 (5) |
O1—Cu1—N2—C14 | 164.1 (5) | O4—C15—C16—C17 | 179.6 (7) |
N1—Cu1—N2—C14 | −89 (1) | C20—C15—C16—C17 | 0 (1) |
O2—Cu1—N2—C14 | −20.6 (5) | C15—C16—C17—C18 | 1 (1) |
O1w—Cu1—N2—C14 | 68.8 (5) | C16—C17—C18—C19 | 0 (1) |
O4—Cu2—N3—C21 | −4.9 (7) | C17—C18—C19—C20 | −1 (1) |
O5—Cu2—N3—C21 | 171.8 (8) | O4—C15—C20—C19 | 178.8 (6) |
N4—Cu2—N3—C21 | 103.0 (9) | C16—C15—C20—C19 | −1.5 (9) |
O2w—Cu2—N3—C21 | −100.6 (7) | O4—C15—C20—C21 | −0.4 (9) |
O4—Cu2—N3—C22 | 175.5 (5) | C16—C15—C20—C21 | 179.3 (6) |
O5—Cu2—N3—C22 | −7.8 (5) | C18—C19—C20—C15 | 2 (1) |
N4—Cu2—N3—C22 | −77 (2) | C18—C19—C20—C21 | −178.5 (7) |
O2w—Cu2—N3—C22 | 79.8 (5) | C22—N3—C21—C20 | −176.1 (6) |
O4—Cu2—N4—C28 | −162.2 (5) | Cu2—N3—C21—C20 | 4 (1) |
N3—Cu2—N4—C28 | 89.9 (13) | C15—C20—C21—N3 | −1 (1) |
O5—Cu2—N4—C28 | 22.1 (5) | C19—C20—C21—N3 | 179.8 (7) |
O2w—Cu2—N4—C28 | −67.3 (5) | C21—N3—C22—C23 | −170.1 (6) |
O4—Cu2—N4—C24 | 18.7 (5) | Cu2—N3—C22—C23 | 9.5 (8) |
N3—Cu2—N4—C24 | −89 (1) | Cu2—O5—C23—O6 | −179.7 (7) |
O5—Cu2—N4—C24 | −156.9 (5) | Cu2—O5—C23—C22 | −0.3 (7) |
O2w—Cu2—N4—C24 | 113.6 (5) | N3—C22—C23—O6 | 173.5 (8) |
C8—N1—C1—C2 | 179.7 (6) | N3—C22—C23—O5 | −6.0 (9) |
Cu1—N1—C1—C2 | −6 (1) | C28—N4—C24—C25 | −4 (1) |
N1—C1—C2—C3 | −177.9 (7) | Cu2—N4—C24—C25 | 175.3 (7) |
N1—C1—C2—C7 | 1 (1) | N4—C24—C25—C26 | 5 (1) |
C7—C2—C3—C4 | −3 (1) | C24—C25—C26—C27 | −4 (1) |
C1—C2—C3—C4 | 175.7 (7) | C25—C26—C27—C28 | 2 (2) |
C2—C3—C4—C5 | 3 (1) | C24—N4—C28—C27 | 2 (1) |
C3—C4—C5—C6 | −1 (1) | Cu2—N4—C28—C27 | −177.1 (7) |
C4—C5—C6—C7 | −1 (1) | C26—C27—C28—N4 | −1 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O3i | 0.85 (1) | 1.95 (3) | 2.749 (6) | 155 (5) |
O1w—H1w2···O5 | 0.85 (1) | 2.46 (5) | 3.114 (6) | 134 (6) |
O1w—H1w2···O6 | 0.85 (1) | 2.41 (3) | 3.169 (6) | 149 (5) |
O2w—H2w2···O2 | 0.85 (1) | 2.39 (3) | 3.121 (6) | 145 (5) |
O2w—H2w2···O3 | 0.85 (1) | 2.39 (2) | 3.169 (7) | 153 (4) |
O2w—H2w1···O6ii | 0.85 (1) | 1.97 (3) | 2.744 (6) | 151 (5) |
Symmetry codes: (i) x+1/2, −y+1, z; (ii) x−1/2, −y, z. |