In the title complex, diaquadinitrato[2-(4-thiazolyl)benzimidazole]copper(II), [Cu(NO
3)
2(C
10H
7N
3S)(H
2O)
2], the Cu atom has a distorted octahedral geometry. Thiabendazole [2-(4-thiazolyl)benzimidazole] acts as a neutral bidentate chelate, coordinating through the imidazole and thiazole N atoms. The equatorial positions are occupied by the two N atoms of the thiabendazole molecule and two O atoms of two water molecules. The axial positions are occupied by two O atoms of two nitrate ions acting as monodentate ligands. The complex units are further self-assembled into a supramolecular motif by extensive inter-ligand O—H
O hydrogen bonds.
Supporting information
CCDC reference: 193699
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.029
- wR factor = 0.077
- Data-to-parameter ratio = 9.8
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level B:
PLAT_031 Alert B Refined Extinction parameter within range .... 2.00 Sigma
Alert Level C:
PLAT_354 Alert C Short O-H Bond (0.82A) O(1) - H(1B) = 0.71 Ang.
PLAT_354 Alert C Short O-H Bond (0.82A) O(2) - H(2A) = 0.71 Ang.
General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced
by the scaled T values. Since the ratio of scaled T's is
identical to the ratio of reported T values, the scaling does
not imply a change to the absorption corrections used in the
study.
Ratio of Tmax expected/reported 0.729
Tmax scaled 0.722 Tmin scaled 0.649
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
2 Alert Level C = Please check
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXS97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON (Spek, 1997).
Crystal data top
[Cu(NO3)2(C10H7N3S)(H2O)2] | F(000) = 860 |
Mr = 424.86 | Dx = 1.856 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.580 (4) Å | Cell parameters from 25 reflections |
b = 20.065 (5) Å | θ = 10–15° |
c = 10.606 (2) Å | µ = 1.63 mm−1 |
β = 109.51 (3)° | T = 293 K |
V = 1520.4 (10) Å3 | Plate, green |
Z = 4 | 0.3 × 0.3 × 0.2 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | 2057 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
ω–2θ scans | h = 0→9 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→23 |
Tmin = 0.89, Tmax = 0.99 | l = −12→11 |
2857 measured reflections | 2 standard reflections every 60 min |
2649 independent reflections | intensity decay: none |
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)] = 0.029 | All H-atom parameters refined |
wR(F2) = 0.077 | w = 1/[σ2(Fo2) + (0.0263P)2 + 1.6719P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.001 |
2649 reflections | Δρmax = 0.35 e Å−3 |
271 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | Extinction correction: SHELXL97 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0008 (4) |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All e.s.d.'s are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.12303 (6) | 0.34522 (2) | 0.40545 (4) | 0.0300 (1) | |
S12 | 0.22328 (14) | 0.39105 (5) | 0.84313 (8) | 0.0427 (3) | |
O1 | 0.1192 (5) | 0.32379 (14) | 0.2246 (3) | 0.0381 (9) | |
O2 | 0.0144 (4) | 0.25740 (12) | 0.4247 (3) | 0.0340 (8) | |
O4A | −0.4458 (4) | 0.39494 (14) | 0.1393 (3) | 0.0679 (11) | |
O4B | −0.2041 (3) | 0.37774 (12) | 0.3127 (2) | 0.0420 (8) | |
O4C | −0.2653 (3) | 0.31208 (12) | 0.1416 (2) | 0.0446 (8) | |
O5A | 0.4214 (3) | 0.28082 (14) | 0.4971 (2) | 0.0508 (9) | |
O5B | 0.6912 (4) | 0.25019 (15) | 0.4934 (3) | 0.0602 (10) | |
O5C | 0.4724 (4) | 0.27265 (17) | 0.3096 (3) | 0.0677 (13) | |
N1 | 0.2067 (4) | 0.43931 (12) | 0.3953 (2) | 0.0287 (8) | |
N3 | 0.2756 (4) | 0.53739 (14) | 0.4974 (3) | 0.0326 (9) | |
N4 | −0.3087 (4) | 0.36156 (13) | 0.1961 (3) | 0.0347 (9) | |
N5 | 0.5286 (4) | 0.26820 (14) | 0.4331 (3) | 0.0391 (10) | |
N14 | 0.1614 (4) | 0.37313 (13) | 0.5956 (2) | 0.0306 (8) | |
C2 | 0.2364 (4) | 0.47293 (15) | 0.5080 (3) | 0.0282 (9) | |
C4 | 0.2924 (5) | 0.60482 (18) | 0.2995 (4) | 0.0412 (11) | |
C5 | 0.2721 (6) | 0.5977 (2) | 0.1663 (4) | 0.0460 (12) | |
C6 | 0.2313 (6) | 0.5361 (2) | 0.1028 (4) | 0.0474 (16) | |
C7 | 0.2072 (5) | 0.47919 (19) | 0.1679 (3) | 0.0390 (11) | |
C8 | 0.2256 (4) | 0.48586 (15) | 0.3030 (3) | 0.0297 (10) | |
C9 | 0.2685 (4) | 0.54799 (16) | 0.3663 (3) | 0.0313 (10) | |
C10 | 0.2220 (4) | 0.43802 (15) | 0.6237 (3) | 0.0295 (10) | |
C11 | 0.2620 (5) | 0.45627 (18) | 0.7527 (3) | 0.0368 (11) | |
C13 | 0.1551 (5) | 0.34309 (19) | 0.7031 (3) | 0.0376 (11) | |
H1A | 0.208 (7) | 0.308 (2) | 0.230 (5) | 0.061 (17)* | |
H1B | 0.037 (8) | 0.307 (3) | 0.185 (5) | 0.09 (2)* | |
H2A | 0.061 (5) | 0.2372 (17) | 0.481 (3) | 0.020 (10)* | |
H2B | −0.094 (6) | 0.259 (2) | 0.425 (4) | 0.053 (14)* | |
H3 | 0.291 (5) | 0.5637 (18) | 0.554 (3) | 0.036 (10)* | |
H4 | 0.321 (5) | 0.6457 (17) | 0.337 (3) | 0.036 (10)* | |
H5 | 0.287 (6) | 0.634 (2) | 0.122 (4) | 0.069 (14)* | |
H6 | 0.230 (5) | 0.5350 (19) | 0.022 (4) | 0.054 (12)* | |
H7 | 0.183 (5) | 0.4374 (19) | 0.130 (4) | 0.045 (10)* | |
H11 | 0.305 (5) | 0.4950 (17) | 0.794 (3) | 0.035 (9)* | |
H13 | 0.121 (5) | 0.3000 (19) | 0.704 (4) | 0.047 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0398 (2) | 0.0255 (2) | 0.0259 (2) | −0.0024 (2) | 0.0126 (2) | −0.0043 (2) |
S12 | 0.0596 (6) | 0.0438 (5) | 0.0255 (4) | 0.0027 (4) | 0.0151 (4) | 0.0007 (4) |
O1 | 0.0405 (17) | 0.0424 (15) | 0.0330 (14) | −0.0031 (14) | 0.0143 (13) | −0.0096 (11) |
O2 | 0.0324 (16) | 0.0302 (13) | 0.0365 (14) | 0.0025 (11) | 0.0076 (12) | 0.0062 (11) |
O4A | 0.0557 (18) | 0.0588 (19) | 0.0653 (19) | 0.0211 (15) | −0.0117 (15) | −0.0047 (15) |
O4B | 0.0396 (14) | 0.0441 (14) | 0.0347 (13) | 0.0069 (11) | 0.0022 (11) | −0.0143 (11) |
O4C | 0.0432 (15) | 0.0455 (15) | 0.0423 (14) | −0.0011 (12) | 0.0106 (12) | −0.0207 (12) |
O5A | 0.0372 (14) | 0.079 (2) | 0.0419 (14) | 0.0059 (13) | 0.0206 (12) | −0.0038 (13) |
O5B | 0.0360 (16) | 0.085 (2) | 0.0636 (18) | 0.0198 (15) | 0.0219 (14) | 0.0257 (16) |
O5C | 0.0576 (19) | 0.108 (3) | 0.0430 (16) | 0.0225 (18) | 0.0241 (14) | 0.0014 (16) |
N1 | 0.0345 (15) | 0.0261 (14) | 0.0249 (13) | −0.0010 (11) | 0.0092 (12) | −0.0027 (10) |
N3 | 0.0414 (17) | 0.0262 (15) | 0.0288 (14) | −0.0030 (12) | 0.0098 (13) | −0.0064 (12) |
N4 | 0.0322 (16) | 0.0344 (16) | 0.0325 (15) | −0.0004 (12) | 0.0043 (13) | −0.0017 (12) |
N5 | 0.0386 (18) | 0.0383 (16) | 0.0458 (18) | −0.0009 (14) | 0.0214 (15) | 0.0018 (14) |
N14 | 0.0388 (16) | 0.0276 (14) | 0.0263 (14) | 0.0002 (12) | 0.0120 (12) | −0.0009 (11) |
C2 | 0.0317 (18) | 0.0258 (16) | 0.0251 (15) | 0.0015 (13) | 0.0070 (14) | −0.0027 (12) |
C4 | 0.046 (2) | 0.0318 (19) | 0.047 (2) | −0.0039 (16) | 0.0172 (18) | 0.0019 (16) |
C5 | 0.055 (2) | 0.041 (2) | 0.048 (2) | −0.0033 (18) | 0.0251 (19) | 0.0111 (18) |
C6 | 0.057 (3) | 0.059 (3) | 0.032 (2) | −0.001 (2) | 0.0226 (19) | 0.0066 (18) |
C7 | 0.051 (2) | 0.041 (2) | 0.0285 (17) | −0.0036 (17) | 0.0178 (16) | −0.0048 (15) |
C8 | 0.0304 (17) | 0.0296 (17) | 0.0299 (16) | −0.0006 (14) | 0.0110 (14) | 0.0008 (13) |
C9 | 0.0291 (18) | 0.0320 (17) | 0.0324 (17) | 0.0004 (14) | 0.0097 (14) | −0.0016 (14) |
C10 | 0.0332 (18) | 0.0272 (16) | 0.0278 (16) | 0.0022 (14) | 0.0097 (14) | −0.0030 (13) |
C11 | 0.047 (2) | 0.0349 (19) | 0.0271 (17) | 0.0013 (16) | 0.0104 (15) | −0.0040 (15) |
C13 | 0.047 (2) | 0.0327 (19) | 0.0358 (18) | −0.0010 (17) | 0.0176 (16) | −0.0005 (16) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.956 (3) | N3—C9 | 1.390 (4) |
Cu1—O2 | 1.984 (3) | N3—C2 | 1.340 (4) |
Cu1—O4B | 2.432 (3) | N14—C13 | 1.305 (4) |
Cu1—O5A | 2.502 (3) | N14—C10 | 1.380 (4) |
Cu1—N1 | 2.006 (3) | N3—H3 | 0.78 (3) |
Cu1—N14 | 2.018 (2) | C2—C10 | 1.448 (4) |
S12—C11 | 1.705 (4) | C4—C9 | 1.386 (5) |
S12—C13 | 1.699 (4) | C4—C5 | 1.376 (6) |
O4A—N4 | 1.214 (4) | C5—C6 | 1.392 (6) |
O4B—N4 | 1.268 (4) | C6—C7 | 1.378 (6) |
O4C—N4 | 1.247 (4) | C7—C8 | 1.399 (4) |
O5A—N5 | 1.246 (4) | C8—C9 | 1.402 (4) |
O5B—N5 | 1.238 (4) | C10—C11 | 1.349 (4) |
O5C—N5 | 1.238 (4) | C4—H4 | 0.91 (3) |
O1—H1B | 0.71 (6) | C5—H5 | 0.89 (4) |
O1—H1A | 0.73 (5) | C6—H6 | 0.85 (4) |
O2—H2B | 0.82 (5) | C7—H7 | 0.92 (4) |
O2—H2A | 0.71 (3) | C11—H11 | 0.90 (3) |
N1—C8 | 1.395 (4) | C13—H13 | 0.90 (4) |
N1—C2 | 1.325 (4) | | |
| | | |
Cu1···O4C | 3.382 (3) | O5B···H2Ax | 2.86 (4) |
Cu1···O5C | 3.459 (4) | O5C···H1A | 2.03 (5) |
Cu1···N3 | 4.050 (4) | O5C···H13ix | 2.34 (4) |
Cu1···O4Ci | 3.941 (3) | N3···Cu1 | 4.050 (4) |
Cu1···H7 | 3.61 (4) | N3···O4Biii | 2.825 (4) |
S12···O4Aii | 3.302 (4) | N4···O5Cvi | 2.953 (5) |
S12···C4iii | 3.691 (5) | N4···H1B | 2.88 (6) |
S12···O5Biv | 3.300 (4) | N4···H11iii | 2.88 (3) |
O1···O4C | 2.759 (5) | N4···H2Av | 2.93 (3) |
O1···O5C | 2.724 (5) | N5···H1A | 2.77 (5) |
O1···C7 | 3.286 (5) | N5···H2Bx | 2.90 (5) |
O1···O5Av | 3.172 (4) | N5···H4viii | 2.89 (3) |
O1···O5Bv | 3.067 (5) | C2···C9viii | 3.563 (5) |
O2···O4C | 3.235 (4) | C4···S12iii | 3.691 (5) |
O2···O5Bvi | 2.783 (5) | C4···O5Aviii | 3.391 (5) |
O2···O4Ci | 2.731 (4) | C4···C10viii | 3.598 (5) |
O4A···O5Cvi | 3.227 (5) | C4···C13iii | 3.541 (6) |
O4A···S12vii | 3.302 (4) | C5···C11viii | 3.515 (6) |
O4A···C11iii | 3.332 (5) | C7···O1 | 3.286 (5) |
O4A···C7vi | 3.225 (5) | C7···O4Ax | 3.225 (5) |
O4B···O5Cvi | 3.226 (4) | C9···C2viii | 3.563 (5) |
O4B···C11iii | 3.400 (5) | C10···C4viii | 3.598 (5) |
O4B···N3iii | 2.825 (4) | C11···C5viii | 3.515 (6) |
O4C···O1 | 2.759 (5) | C11···O4Aiii | 3.332 (5) |
O4C···O5Av | 3.045 (4) | C11···O4Biii | 3.400 (5) |
O4C···Cu1 | 3.382 (3) | C13···O5Civ | 3.104 (5) |
O4C···Cu1v | 3.941 (3) | C13···C4iii | 3.541 (6) |
O4C···O2v | 2.731 (4) | C13···O4Ci | 3.278 (5) |
O4C···O5Cvi | 3.181 (4) | C11···H3 | 3.07 (3) |
O4C···C13v | 3.278 (5) | C13···H2A | 3.07 (3) |
O4C···O2 | 3.235 (4) | H1A···O5C | 2.03 (5) |
O5A···O4Ci | 3.045 (4) | H1A···N5 | 2.77 (5) |
O5A···C4viii | 3.391 (5) | H1A···O5Bv | 2.73 (5) |
O5A···O1i | 3.172 (4) | H1B···O4C | 2.18 (6) |
O5B···S12ix | 3.300 (4) | H1B···N4 | 2.88 (6) |
O5B···O1i | 3.067 (5) | H1B···O5Av | 2.58 (6) |
O5B···O2x | 2.783 (5) | H1B···O5Bv | 2.90 (6) |
O5C···O1 | 2.724 (5) | H2A···O5Bvi | 2.86 (4) |
O5C···C13ix | 3.104 (5) | H2A···C13 | 3.07 (3) |
O5C···O4Cx | 3.181 (4) | H2A···H13 | 2.58 (5) |
O5C···O4Bx | 3.226 (4) | H2A···O4Ci | 2.03 (3) |
O5C···N4x | 2.953 (5) | H2A···N4i | 2.93 (3) |
O5C···Cu1 | 3.459 (4) | H2B···O5Bvi | 2.00 (5) |
O5C···O4Ax | 3.227 (5) | H2B···N5vi | 2.90 (5) |
O1···H7 | 2.60 (4) | H3···C11 | 3.07 (3) |
O4A···H7vi | 2.91 (4) | H3···O4Biii | 2.11 (3) |
O4A···H11iii | 2.45 (3) | H4···O5Aviii | 2.61 (3) |
O4B···H3iii | 2.11 (3) | H4···O5Bviii | 2.78 (3) |
O4B···H11iii | 2.79 (3) | H4···N5viii | 2.89 (3) |
O4C···H1B | 2.18 (6) | H7···Cu1 | 3.61 (4) |
O4C···H13v | 2.57 (4) | H7···O1 | 2.60 (4) |
O4C···H2Av | 2.03 (3) | H7···O4Ax | 2.91 (4) |
O5A···H1Bi | 2.58 (6) | H11···O4Aiii | 2.45 (3) |
O5A···H4viii | 2.61 (3) | H11···O4Biii | 2.79 (3) |
O5B···H1Bi | 2.90 (6) | H11···N4iii | 2.88 (3) |
O5B···H4viii | 2.78 (3) | H13···H2A | 2.58 (5) |
O5B···H2Bx | 2.00 (5) | H13···O4Ci | 2.57 (4) |
O5B···H1Ai | 2.73 (5) | H13···O5Civ | 2.34 (4) |
| | | |
O1—Cu1—O2 | 92.00 (13) | Cu1—N14—C10 | 113.84 (19) |
O1—Cu1—O4B | 89.03 (12) | C10—N14—C13 | 110.7 (3) |
O1—Cu1—O5A | 89.02 (12) | C2—N3—H3 | 125 (2) |
O1—Cu1—N1 | 93.19 (11) | C9—N3—H3 | 128 (2) |
O1—Cu1—N14 | 172.14 (14) | N1—C2—C10 | 118.7 (3) |
O2—Cu1—O4B | 82.98 (11) | N3—C2—C10 | 128.3 (3) |
O2—Cu1—O5A | 81.59 (11) | N1—C2—N3 | 113.0 (3) |
O2—Cu1—N1 | 172.25 (13) | C5—C4—C9 | 116.8 (3) |
O2—Cu1—N14 | 94.01 (12) | C4—C5—C6 | 121.3 (4) |
O4B—Cu1—O5A | 164.37 (9) | C5—C6—C7 | 122.6 (4) |
O4B—Cu1—N1 | 91.36 (11) | C6—C7—C8 | 116.7 (3) |
O4B—Cu1—N14 | 96.72 (10) | N1—C8—C7 | 131.0 (3) |
O5A—Cu1—N1 | 104.24 (11) | N1—C8—C9 | 108.7 (3) |
O5A—Cu1—N14 | 86.86 (10) | C7—C8—C9 | 120.2 (3) |
N1—Cu1—N14 | 81.36 (10) | N3—C9—C8 | 105.6 (3) |
C11—S12—C13 | 90.13 (17) | C4—C9—C8 | 122.4 (3) |
Cu1—O4B—N4 | 123.1 (2) | N3—C9—C4 | 132.0 (3) |
Cu1—O5A—N5 | 124.22 (19) | N14—C10—C2 | 112.8 (3) |
Cu1—O1—H1A | 108 (4) | N14—C10—C11 | 114.9 (3) |
Cu1—O1—H1B | 114 (5) | C2—C10—C11 | 132.3 (3) |
H1A—O1—H1B | 116 (6) | S12—C11—C10 | 109.8 (3) |
Cu1—O2—H2A | 119 (3) | S12—C13—N14 | 114.4 (3) |
Cu1—O2—H2B | 115 (3) | C5—C4—H4 | 118 (2) |
H2A—O2—H2B | 104 (4) | C9—C4—H4 | 125 (2) |
Cu1—N1—C2 | 113.1 (2) | C4—C5—H5 | 118 (3) |
Cu1—N1—C8 | 140.94 (19) | C6—C5—H5 | 121 (3) |
C2—N1—C8 | 105.4 (2) | C5—C6—H6 | 116 (3) |
C2—N3—C9 | 107.2 (3) | C7—C6—H6 | 121 (3) |
O4A—N4—O4C | 121.6 (3) | C6—C7—H7 | 125 (3) |
O4B—N4—O4C | 118.7 (3) | C8—C7—H7 | 118 (3) |
O4A—N4—O4B | 119.7 (3) | S12—C11—H11 | 119 (2) |
O5A—N5—O5C | 120.3 (3) | C10—C11—H11 | 131 (2) |
O5A—N5—O5B | 119.7 (3) | S12—C13—H13 | 123 (3) |
O5B—N5—O5C | 119.9 (3) | N14—C13—H13 | 123 (3) |
Cu1—N14—C13 | 135.2 (2) | | |
| | | |
O1—Cu1—O4B—N4 | 16.5 (2) | C8—N1—C2—C10 | 178.6 (3) |
O2—Cu1—O4B—N4 | −75.7 (2) | C2—N1—C8—C7 | −179.1 (4) |
N1—Cu1—O4B—N4 | 109.7 (2) | C2—N1—C8—C9 | 0.3 (4) |
N14—Cu1—O4B—N4 | −168.9 (2) | Cu1—N1—C2—C10 | 5.2 (4) |
O1—Cu1—O5A—N5 | 21.3 (3) | Cu1—N1—C8—C7 | −8.7 (6) |
O2—Cu1—O5A—N5 | 113.5 (3) | C9—N3—C2—N1 | 1.0 (4) |
N1—Cu1—O5A—N5 | −71.7 (3) | C2—N3—C9—C8 | −0.8 (4) |
N14—Cu1—O5A—N5 | −152.0 (3) | C9—N3—C2—C10 | −178.3 (3) |
O1—Cu1—N1—C2 | −177.0 (3) | C2—N3—C9—C4 | 178.2 (4) |
O4B—Cu1—N1—C2 | 93.9 (2) | C10—N14—C13—S12 | −0.5 (4) |
O5A—Cu1—N1—C2 | −87.2 (2) | C13—N14—C10—C11 | 0.4 (4) |
N14—Cu1—N1—C2 | −2.7 (2) | Cu1—N14—C13—S12 | 173.9 (2) |
O1—Cu1—N1—C8 | 13.1 (4) | Cu1—N14—C10—C11 | −175.3 (3) |
O4B—Cu1—N1—C8 | −76.0 (4) | C13—N14—C10—C2 | 178.4 (3) |
O5A—Cu1—N1—C8 | 102.9 (4) | Cu1—N14—C10—C2 | 2.7 (4) |
N14—Cu1—N1—C8 | −172.6 (4) | N1—C2—C10—N14 | −5.3 (4) |
N1—Cu1—N14—C10 | −0.1 (2) | N1—C2—C10—C11 | 172.2 (4) |
O2—Cu1—N14—C13 | 11.9 (4) | N3—C2—C10—N14 | 174.0 (3) |
O4B—Cu1—N14—C13 | 95.3 (4) | N3—C2—C10—C11 | −8.4 (6) |
O5A—Cu1—N14—C13 | −69.4 (4) | C5—C4—C9—N3 | −178.8 (4) |
O2—Cu1—N14—C10 | −173.9 (2) | C9—C4—C5—C6 | −0.6 (6) |
O4B—Cu1—N14—C10 | −90.5 (2) | C5—C4—C9—C8 | 0.0 (6) |
O5A—Cu1—N14—C10 | 104.8 (2) | C4—C5—C6—C7 | 0.6 (7) |
N1—Cu1—N14—C13 | −174.4 (4) | C5—C6—C7—C8 | 0.0 (6) |
C11—S12—C13—N14 | 0.4 (3) | C6—C7—C8—C9 | −0.7 (5) |
C13—S12—C11—C10 | −0.2 (3) | C6—C7—C8—N1 | 178.7 (4) |
Cu1—O4B—N4—O4A | −156.4 (3) | C7—C8—C9—C4 | 0.7 (5) |
Cu1—O4B—N4—O4C | 22.3 (4) | N1—C8—C9—N3 | 0.3 (4) |
Cu1—O5A—N5—O5B | 163.2 (2) | N1—C8—C9—C4 | −178.8 (3) |
Cu1—O5A—N5—O5C | −17.9 (4) | C7—C8—C9—N3 | 179.7 (3) |
Cu1—N1—C8—C9 | 170.7 (3) | N14—C10—C11—S12 | −0.1 (4) |
Cu1—N1—C2—N3 | −174.3 (2) | C2—C10—C11—S12 | −177.6 (3) |
C8—N1—C2—N3 | −0.8 (4) | | |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x+1, y, z+1; (iii) −x, −y+1, −z+1; (iv) x−1/2, −y+1/2, z+1/2; (v) x−1/2, −y+1/2, z−1/2; (vi) x−1, y, z; (vii) x−1, y, z−1; (viii) −x+1, −y+1, −z+1; (ix) x+1/2, −y+1/2, z−1/2; (x) x+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O5C | 0.73 (5) | 2.03 (5) | 2.724 (5) | 161 (5) |
O1—H1B···O4C | 0.71 (6) | 2.18 (6) | 2.759 (5) | 139 (6) |
O1—H1B···O5Av | 0.71 (6) | 2.58 (6) | 3.172 (4) | 142 (6) |
O2—H2A···O4Ci | 0.71 (3) | 2.03 (3) | 2.731 (4) | 170 (4) |
O2—H2B···O5Bvi | 0.82 (5) | 2.00 (5) | 2.783 (5) | 159 (4) |
N3—H3···O4Biii | 0.78 (3) | 2.11 (3) | 2.825 (4) | 154 (4) |
C11—H11···O4Aiii | 0.90 (3) | 2.45 (3) | 3.332 (5) | 166 (3) |
C13—H13···O4Ci | 0.90 (4) | 2.57 (4) | 3.278 (5) | 135 (3) |
C13—H13···O5Civ | 0.90 (4) | 2.34 (4) | 3.104 (5) | 142 (3) |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (iii) −x, −y+1, −z+1; (iv) x−1/2, −y+1/2, z+1/2; (v) x−1/2, −y+1/2, z−1/2; (vi) x−1, y, z. |