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metal-organic compounds
In the title compound, [Cu(C15H11N2O2)2(C5H7NO)2](C15H12N2O2)2, the CuII ion, lying on an inversion centre, is coordinated in a square-planar coordination geometry; two other 5,5-diphenylhydantoin molecules are uncoordinated. The crystal structure includes intermolecular N—HO hydrogen bonds, forming a two-dimensional network.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806042012/bh2048sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806042012/bh2048Isup2.hkl |
CCDC reference: 618985
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.014 Å
- R factor = 0.083
- wR factor = 0.241
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 40 Perc. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.35 Ratio PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 15
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.
trans-Bis(5,5-Diphenylhydantoinato-N3)Bis(furfurylamine)copper(II) Bis(5,5-Diphenylhydantoinatoin) top
Crystal data top
[Cu(C15H11N2O2)2(C5H7NO)2](C15H12N2O2)2 | Z = 1 |
Mr = 1264.82 | F(000) = 659 |
Triclinic, P1 | Dx = 1.363 Mg m−3 |
Hall symbol: -P 1 | Melting point: 564 K |
a = 9.736 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.193 (9) Å | Cell parameters from 788 reflections |
c = 14.215 (10) Å | θ = 1.7–25.0° |
α = 109.439 (10)° | µ = 0.43 mm−1 |
β = 108.647 (10)° | T = 298 K |
γ = 100.795 (9)° | Block, blue |
V = 1540.7 (19) Å3 | 0.48 × 0.19 × 0.09 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 5266 independent reflections |
Radiation source: fine-focus sealed tube | 2130 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.094 |
φ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.822, Tmax = 0.963 | k = −15→14 |
7816 measured reflections | l = −16→12 |
Refinement top
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)] = 0.083 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.241 | H-atom parameters constrained |
S = 0.98 | w = 1/σ2(Fo2) |
5266 reflections | (Δ/σ)max < 0.001 |
412 parameters | Δρmax = 0.52 e Å−3 |
180 restraints | Δρmin = −0.78 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.5000 | 0.5000 | 0.5000 | 0.0294 (5) | |
N1 | 0.1341 (7) | 0.6236 (4) | 0.4960 (5) | 0.0301 (16) | |
H1 | 0.0359 | 0.6061 | 0.4707 | 0.036* | |
N2 | 0.3674 (6) | 0.5988 (4) | 0.5352 (4) | 0.0224 (15) | |
N3 | 0.0594 (7) | 0.1496 (4) | 0.0769 (5) | 0.0385 (18) | |
H3 | −0.0065 | 0.1039 | 0.0115 | 0.046* | |
N4 | 0.2408 (7) | 0.2117 (5) | 0.2413 (5) | 0.0381 (18) | |
H4 | 0.3092 | 0.2109 | 0.2969 | 0.046* | |
N5 | 0.4053 (7) | 0.3913 (4) | 0.5489 (5) | 0.0306 (16) | |
H5A | 0.3072 | 0.3891 | 0.5320 | 0.037* | |
H5B | 0.4028 | 0.3218 | 0.5075 | 0.037* | |
O1 | 0.1489 (6) | 0.4531 (4) | 0.4936 (4) | 0.0338 (14) | |
O2 | 0.5168 (5) | 0.7824 (3) | 0.5885 (4) | 0.0327 (14) | |
O3 | 0.1582 (7) | 0.0218 (4) | 0.1274 (4) | 0.0491 (17) | |
O4 | 0.2697 (6) | 0.4029 (4) | 0.3113 (4) | 0.0358 (14) | |
O5 | 0.2510 (8) | 0.2890 (5) | 0.6650 (6) | 0.076 (2) | |
C1 | 0.2103 (8) | 0.5506 (6) | 0.5076 (6) | 0.0229 (18) | |
C2 | 0.3914 (8) | 0.7101 (5) | 0.5579 (6) | 0.0242 (18) | |
C3 | 0.2407 (8) | 0.7374 (5) | 0.5324 (6) | 0.0241 (18) | |
C4 | 0.2182 (8) | 0.7790 (6) | 0.4417 (6) | 0.0262 (18) | |
C5 | 0.1298 (9) | 0.7066 (7) | 0.3329 (7) | 0.044 (2) | |
H5 | 0.0808 | 0.6304 | 0.3134 | 0.052* | |
C6 | 0.1135 (11) | 0.7459 (8) | 0.2532 (7) | 0.060 (3) | |
H6 | 0.0530 | 0.6960 | 0.1803 | 0.072* | |
C7 | 0.1852 (12) | 0.8580 (8) | 0.2796 (8) | 0.058 (3) | |
H7 | 0.1730 | 0.8843 | 0.2253 | 0.069* | |
C8 | 0.2750 (11) | 0.9302 (7) | 0.3874 (8) | 0.058 (3) | |
H8 | 0.3263 | 1.0058 | 0.4063 | 0.069* | |
C9 | 0.2899 (9) | 0.8911 (6) | 0.4685 (7) | 0.043 (2) | |
H9 | 0.3488 | 0.9413 | 0.5416 | 0.052* | |
C10 | 0.2307 (11) | 0.8198 (6) | 0.6314 (7) | 0.038 (2) | |
C11 | 0.3456 (12) | 0.8685 (7) | 0.7356 (7) | 0.056 (2) | |
H11 | 0.4378 | 0.8538 | 0.7464 | 0.067* | |
C12 | 0.3275 (15) | 0.9394 (8) | 0.8253 (9) | 0.074 (3) | |
H12 | 0.4071 | 0.9727 | 0.8948 | 0.089* | |
C13 | 0.1924 (15) | 0.9588 (7) | 0.8093 (9) | 0.071 (3) | |
H13 | 0.1791 | 1.0052 | 0.8690 | 0.085* | |
C14 | 0.0762 (13) | 0.9126 (7) | 0.7088 (9) | 0.067 (3) | |
H14 | −0.0164 | 0.9264 | 0.6996 | 0.080* | |
C15 | 0.0964 (12) | 0.8432 (7) | 0.6181 (8) | 0.056 (2) | |
H15 | 0.0176 | 0.8130 | 0.5484 | 0.067* | |
C16 | 0.1511 (9) | 0.1161 (6) | 0.1429 (6) | 0.034 (2) | |
C17 | 0.2065 (8) | 0.3070 (6) | 0.2384 (6) | 0.0280 (19) | |
C18 | 0.0803 (9) | 0.2701 (5) | 0.1248 (6) | 0.029 (2) | |
C19 | 0.1474 (9) | 0.3335 (6) | 0.0684 (6) | 0.033 (2) | |
C20 | 0.2196 (11) | 0.2895 (7) | 0.0056 (7) | 0.051 (3) | |
H20 | 0.2237 | 0.2166 | −0.0068 | 0.061* | |
C21 | 0.2877 (11) | 0.3491 (9) | −0.0407 (8) | 0.061 (3) | |
H21 | 0.3325 | 0.3153 | −0.0860 | 0.074* | |
C22 | 0.2882 (11) | 0.4592 (9) | −0.0189 (8) | 0.066 (3) | |
H22 | 0.3375 | 0.5015 | −0.0467 | 0.079* | |
C23 | 0.2165 (12) | 0.5054 (7) | 0.0435 (8) | 0.063 (3) | |
H23 | 0.2144 | 0.5789 | 0.0565 | 0.075* | |
C24 | 0.1462 (10) | 0.4444 (6) | 0.0880 (7) | 0.048 (2) | |
H24 | 0.0982 | 0.4775 | 0.1311 | 0.058* | |
C25 | −0.0681 (9) | 0.2897 (6) | 0.1274 (6) | 0.032 (2) | |
C26 | −0.1999 (11) | 0.2362 (7) | 0.0284 (7) | 0.052 (3) | |
H26 | −0.1946 | 0.1908 | −0.0355 | 0.062* | |
C27 | −0.3385 (11) | 0.2514 (8) | 0.0260 (8) | 0.059 (3) | |
H27 | −0.4260 | 0.2158 | −0.0395 | 0.071* | |
C28 | −0.3461 (11) | 0.3187 (8) | 0.1201 (9) | 0.059 (3) | |
H28 | −0.4387 | 0.3288 | 0.1183 | 0.071* | |
C29 | −0.2163 (11) | 0.3716 (8) | 0.2174 (8) | 0.057 (3) | |
H29 | −0.2215 | 0.4174 | 0.2811 | 0.068* | |
C30 | −0.0795 (11) | 0.3564 (7) | 0.2201 (7) | 0.045 (2) | |
H30 | 0.0071 | 0.3920 | 0.2861 | 0.054* | |
C31 | 0.4710 (11) | 0.4074 (7) | 0.6633 (7) | 0.054 (2) | |
H31A | 0.4581 | 0.4751 | 0.7087 | 0.064* | |
H31B | 0.5803 | 0.4198 | 0.6868 | 0.064* | |
C32 | 0.4005 (12) | 0.3101 (7) | 0.6804 (8) | 0.054 (2) | |
C33 | 0.4466 (12) | 0.2282 (8) | 0.6986 (8) | 0.064 (3) | |
H33 | 0.5437 | 0.2218 | 0.7110 | 0.077* | |
C34 | 0.3191 (14) | 0.1508 (8) | 0.6956 (9) | 0.071 (3) | |
H34 | 0.3173 | 0.0849 | 0.7063 | 0.085* | |
C35 | 0.2096 (14) | 0.1898 (8) | 0.6754 (9) | 0.078 (3) | |
H35 | 0.1122 | 0.1552 | 0.6686 | 0.093* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0263 (9) | 0.0161 (7) | 0.0490 (9) | 0.0062 (6) | 0.0169 (7) | 0.0165 (7) |
N1 | 0.018 (4) | 0.017 (3) | 0.049 (4) | 0.003 (3) | 0.008 (3) | 0.013 (3) |
N2 | 0.018 (3) | 0.012 (3) | 0.028 (3) | 0.001 (3) | 0.000 (3) | 0.009 (3) |
N3 | 0.042 (4) | 0.012 (3) | 0.036 (4) | 0.002 (3) | −0.004 (3) | 0.006 (3) |
N4 | 0.039 (4) | 0.024 (4) | 0.032 (4) | 0.010 (3) | −0.005 (3) | 0.009 (3) |
N5 | 0.029 (4) | 0.015 (3) | 0.044 (4) | 0.009 (3) | 0.013 (3) | 0.010 (3) |
O1 | 0.031 (3) | 0.015 (3) | 0.061 (4) | 0.008 (2) | 0.025 (3) | 0.017 (3) |
O2 | 0.022 (3) | 0.017 (3) | 0.046 (3) | −0.003 (2) | 0.004 (3) | 0.014 (2) |
O3 | 0.065 (4) | 0.016 (3) | 0.044 (4) | 0.013 (3) | −0.003 (3) | 0.011 (3) |
O4 | 0.028 (3) | 0.021 (3) | 0.037 (3) | 0.000 (2) | 0.003 (3) | 0.003 (3) |
O5 | 0.078 (5) | 0.059 (4) | 0.109 (5) | 0.018 (3) | 0.046 (4) | 0.054 (4) |
C1 | 0.018 (4) | 0.021 (4) | 0.029 (4) | 0.008 (3) | 0.009 (4) | 0.009 (3) |
C2 | 0.019 (4) | 0.019 (4) | 0.028 (4) | 0.001 (3) | 0.008 (4) | 0.008 (3) |
C3 | 0.023 (4) | 0.021 (4) | 0.036 (4) | 0.011 (3) | 0.012 (4) | 0.017 (4) |
C4 | 0.023 (4) | 0.022 (4) | 0.037 (5) | 0.009 (3) | 0.011 (4) | 0.017 (4) |
C5 | 0.039 (6) | 0.035 (5) | 0.047 (6) | 0.004 (4) | 0.012 (5) | 0.018 (5) |
C6 | 0.057 (7) | 0.070 (7) | 0.039 (6) | 0.017 (6) | 0.009 (5) | 0.020 (5) |
C7 | 0.081 (8) | 0.068 (7) | 0.041 (6) | 0.035 (6) | 0.027 (6) | 0.035 (6) |
C8 | 0.072 (7) | 0.048 (6) | 0.075 (7) | 0.021 (5) | 0.039 (6) | 0.043 (6) |
C9 | 0.038 (5) | 0.033 (5) | 0.056 (6) | 0.006 (4) | 0.018 (5) | 0.021 (4) |
C10 | 0.056 (5) | 0.024 (4) | 0.056 (5) | 0.021 (4) | 0.040 (4) | 0.021 (4) |
C11 | 0.084 (6) | 0.042 (5) | 0.053 (5) | 0.027 (4) | 0.039 (5) | 0.019 (4) |
C12 | 0.103 (7) | 0.055 (5) | 0.064 (5) | 0.022 (5) | 0.041 (6) | 0.021 (5) |
C13 | 0.109 (7) | 0.034 (5) | 0.082 (6) | 0.016 (5) | 0.069 (6) | 0.015 (5) |
C14 | 0.084 (6) | 0.042 (5) | 0.093 (6) | 0.024 (5) | 0.065 (5) | 0.022 (5) |
C15 | 0.075 (6) | 0.038 (4) | 0.077 (5) | 0.028 (4) | 0.055 (5) | 0.022 (4) |
C16 | 0.032 (5) | 0.030 (5) | 0.030 (5) | 0.006 (4) | 0.004 (4) | 0.013 (4) |
C17 | 0.024 (4) | 0.013 (4) | 0.038 (5) | −0.001 (3) | 0.007 (4) | 0.010 (4) |
C18 | 0.032 (5) | 0.013 (4) | 0.032 (5) | 0.001 (3) | 0.002 (4) | 0.009 (3) |
C19 | 0.034 (5) | 0.026 (4) | 0.039 (5) | 0.009 (4) | 0.012 (4) | 0.015 (4) |
C20 | 0.060 (7) | 0.040 (5) | 0.050 (6) | 0.016 (5) | 0.022 (5) | 0.017 (5) |
C21 | 0.055 (7) | 0.071 (7) | 0.064 (7) | 0.022 (6) | 0.030 (6) | 0.029 (6) |
C22 | 0.055 (7) | 0.076 (8) | 0.077 (8) | 0.007 (6) | 0.030 (6) | 0.048 (7) |
C23 | 0.070 (8) | 0.039 (6) | 0.087 (8) | 0.009 (5) | 0.037 (7) | 0.037 (6) |
C24 | 0.060 (7) | 0.031 (5) | 0.049 (6) | 0.006 (4) | 0.021 (5) | 0.017 (4) |
C25 | 0.027 (5) | 0.020 (4) | 0.036 (5) | 0.000 (4) | 0.000 (4) | 0.012 (4) |
C26 | 0.047 (6) | 0.040 (5) | 0.048 (6) | 0.012 (5) | 0.004 (5) | 0.012 (5) |
C27 | 0.042 (7) | 0.056 (6) | 0.059 (7) | 0.013 (5) | 0.003 (6) | 0.021 (6) |
C28 | 0.041 (7) | 0.069 (7) | 0.079 (8) | 0.018 (5) | 0.033 (6) | 0.039 (6) |
C29 | 0.047 (7) | 0.077 (7) | 0.060 (7) | 0.031 (6) | 0.031 (6) | 0.029 (6) |
C30 | 0.041 (6) | 0.042 (5) | 0.045 (6) | 0.013 (4) | 0.015 (5) | 0.012 (5) |
C31 | 0.060 (5) | 0.044 (5) | 0.064 (5) | 0.007 (4) | 0.027 (4) | 0.035 (4) |
C32 | 0.062 (6) | 0.049 (5) | 0.071 (5) | 0.011 (4) | 0.045 (5) | 0.036 (4) |
C33 | 0.065 (6) | 0.062 (5) | 0.095 (6) | 0.028 (4) | 0.044 (5) | 0.053 (5) |
C34 | 0.086 (7) | 0.050 (5) | 0.097 (6) | 0.018 (5) | 0.054 (6) | 0.040 (5) |
C35 | 0.075 (6) | 0.065 (6) | 0.106 (6) | 0.004 (5) | 0.049 (6) | 0.051 (5) |
Geometric parameters (Å, º) top
Cu1—N5i | 1.992 (6) | C11—H11 | 0.9300 |
Cu1—N5 | 1.992 (6) | C12—C13 | 1.349 (14) |
Cu1—N2 | 2.055 (6) | C12—H12 | 0.9300 |
Cu1—N2i | 2.055 (6) | C13—C14 | 1.349 (14) |
Cu1—O4 | 2.579 (5) | C13—H13 | 0.9300 |
N1—C1 | 1.342 (8) | C14—C15 | 1.409 (12) |
N1—C3 | 1.468 (8) | C14—H14 | 0.9300 |
N1—H1 | 0.8600 | C15—H15 | 0.9300 |
N2—C2 | 1.350 (8) | C17—C18 | 1.530 (10) |
N2—C1 | 1.408 (9) | C18—C25 | 1.525 (11) |
N3—C16 | 1.327 (9) | C18—C19 | 1.532 (10) |
N3—C18 | 1.450 (8) | C19—C20 | 1.355 (11) |
N3—H3 | 0.8600 | C19—C24 | 1.399 (10) |
N4—C17 | 1.370 (8) | C20—C21 | 1.386 (12) |
N4—C16 | 1.393 (9) | C20—H20 | 0.9300 |
N4—H4 | 0.8600 | C21—C22 | 1.379 (12) |
N5—C31 | 1.467 (10) | C21—H21 | 0.9300 |
N5—H5A | 0.9000 | C22—C23 | 1.356 (13) |
N5—H5B | 0.9000 | C22—H22 | 0.9300 |
O1—C1 | 1.231 (8) | C23—C24 | 1.388 (11) |
O2—C2 | 1.240 (8) | C23—H23 | 0.9300 |
O3—C16 | 1.209 (8) | C24—H24 | 0.9300 |
O4—C17 | 1.217 (7) | C25—C30 | 1.371 (11) |
O5—C32 | 1.359 (11) | C25—C26 | 1.404 (10) |
O5—C35 | 1.366 (10) | C26—C27 | 1.392 (12) |
C2—C3 | 1.536 (10) | C26—H26 | 0.9300 |
C3—C10 | 1.511 (10) | C27—C28 | 1.371 (12) |
C3—C4 | 1.531 (9) | C27—H27 | 0.9300 |
C4—C9 | 1.374 (9) | C28—C29 | 1.381 (12) |
C4—C5 | 1.379 (10) | C28—H28 | 0.9300 |
C5—C6 | 1.373 (11) | C29—C30 | 1.374 (11) |
C5—H5 | 0.9300 | C29—H29 | 0.9300 |
C6—C7 | 1.376 (12) | C30—H30 | 0.9300 |
C6—H6 | 0.9300 | C31—C32 | 1.470 (10) |
C7—C8 | 1.371 (11) | C31—H31A | 0.9700 |
C7—H7 | 0.9300 | C31—H31B | 0.9700 |
C8—C9 | 1.391 (11) | C32—C33 | 1.314 (11) |
C8—H8 | 0.9300 | C33—C34 | 1.431 (13) |
C9—H9 | 0.9300 | C33—H33 | 0.9300 |
C10—C15 | 1.369 (12) | C34—C35 | 1.262 (13) |
C10—C11 | 1.377 (11) | C34—H34 | 0.9300 |
C11—C12 | 1.393 (12) | C35—H35 | 0.9300 |
N5i—Cu1—N5 | 180.0 (2) | C13—C14—C15 | 119.4 (11) |
N5i—Cu1—N2 | 88.8 (2) | C13—C14—H14 | 120.3 |
N5—Cu1—N2 | 91.2 (2) | C15—C14—H14 | 120.3 |
N5i—Cu1—N2i | 91.2 (2) | C10—C15—C14 | 120.6 (10) |
N5—Cu1—N2i | 88.8 (2) | C10—C15—H15 | 119.7 |
N2—Cu1—N2i | 180.000 (2) | C14—C15—H15 | 119.7 |
N5i—Cu1—O4 | 89.3 (2) | O3—C16—N3 | 129.3 (7) |
N5—Cu1—O4 | 90.7 (2) | O3—C16—N4 | 123.4 (7) |
N2—Cu1—O4 | 81.88 (19) | N3—C16—N4 | 107.2 (6) |
N2i—Cu1—O4 | 98.12 (19) | O4—C17—N4 | 126.0 (7) |
C1—N1—C3 | 111.0 (6) | O4—C17—C18 | 127.2 (6) |
C1—N1—H1 | 124.5 | N4—C17—C18 | 106.7 (6) |
C3—N1—H1 | 124.5 | N3—C18—C25 | 111.1 (6) |
C2—N2—C1 | 105.9 (6) | N3—C18—C17 | 100.4 (5) |
C2—N2—Cu1 | 130.0 (5) | C25—C18—C17 | 113.5 (6) |
C1—N2—Cu1 | 121.8 (4) | N3—C18—C19 | 112.1 (6) |
C16—N3—C18 | 114.0 (6) | C25—C18—C19 | 112.2 (6) |
C16—N3—H3 | 123.0 | C17—C18—C19 | 106.9 (6) |
C18—N3—H3 | 123.0 | C20—C19—C24 | 117.6 (8) |
C17—N4—C16 | 111.6 (6) | C20—C19—C18 | 122.3 (7) |
C17—N4—H4 | 124.2 | C24—C19—C18 | 119.9 (8) |
C16—N4—H4 | 124.2 | C19—C20—C21 | 122.5 (9) |
C31—N5—Cu1 | 121.1 (5) | C19—C20—H20 | 118.7 |
C31—N5—H5A | 107.1 | C21—C20—H20 | 118.7 |
Cu1—N5—H5A | 107.1 | C22—C21—C20 | 119.2 (10) |
C31—N5—H5B | 107.1 | C22—C21—H21 | 120.4 |
Cu1—N5—H5B | 107.1 | C20—C21—H21 | 120.4 |
H5A—N5—H5B | 106.8 | C23—C22—C21 | 119.6 (9) |
C17—O4—Cu1 | 136.0 (5) | C23—C22—H22 | 120.2 |
C32—O5—C35 | 105.7 (8) | C21—C22—H22 | 120.2 |
O1—C1—N1 | 123.8 (7) | C22—C23—C24 | 120.8 (9) |
O1—C1—N2 | 124.8 (6) | C22—C23—H23 | 119.6 |
N1—C1—N2 | 111.5 (6) | C24—C23—H23 | 119.6 |
O2—C2—N2 | 125.6 (7) | C23—C24—C19 | 120.2 (9) |
O2—C2—C3 | 122.3 (6) | C23—C24—H24 | 119.9 |
N2—C2—C3 | 111.9 (6) | C19—C24—H24 | 119.9 |
N1—C3—C10 | 109.3 (6) | C30—C25—C26 | 118.7 (8) |
N1—C3—C4 | 113.6 (6) | C30—C25—C18 | 123.9 (7) |
C10—C3—C4 | 112.2 (6) | C26—C25—C18 | 117.4 (7) |
N1—C3—C2 | 98.8 (5) | C27—C26—C25 | 119.8 (9) |
C10—C3—C2 | 113.9 (6) | C27—C26—H26 | 120.1 |
C4—C3—C2 | 108.5 (6) | C25—C26—H26 | 120.1 |
C9—C4—C5 | 118.6 (7) | C28—C27—C26 | 120.1 (9) |
C9—C4—C3 | 119.5 (7) | C28—C27—H27 | 120.0 |
C5—C4—C3 | 121.9 (6) | C26—C27—H27 | 120.0 |
C6—C5—C4 | 120.6 (7) | C27—C28—C29 | 120.0 (9) |
C6—C5—H5 | 119.7 | C27—C28—H28 | 120.0 |
C4—C5—H5 | 119.7 | C29—C28—H28 | 120.0 |
C5—C6—C7 | 121.0 (8) | C30—C29—C28 | 120.0 (9) |
C5—C6—H6 | 119.5 | C30—C29—H29 | 120.0 |
C7—C6—H6 | 119.5 | C28—C29—H29 | 120.0 |
C8—C7—C6 | 118.8 (8) | C25—C30—C29 | 121.4 (8) |
C8—C7—H7 | 120.6 | C25—C30—H30 | 119.3 |
C6—C7—H7 | 120.6 | C29—C30—H30 | 119.3 |
C7—C8—C9 | 120.4 (8) | N5—C31—C32 | 113.2 (7) |
C7—C8—H8 | 119.8 | N5—C31—H31A | 108.9 |
C9—C8—H8 | 119.8 | C32—C31—H31A | 108.9 |
C4—C9—C8 | 120.6 (8) | N5—C31—H31B | 108.9 |
C4—C9—H9 | 119.7 | C32—C31—H31B | 108.9 |
C8—C9—H9 | 119.7 | H31A—C31—H31B | 107.8 |
C15—C10—C11 | 117.7 (8) | C33—C32—O5 | 109.0 (8) |
C15—C10—C3 | 118.1 (8) | C33—C32—C31 | 133.5 (10) |
C11—C10—C3 | 124.1 (8) | O5—C32—C31 | 117.2 (9) |
C10—C11—C12 | 121.8 (10) | C32—C33—C34 | 107.1 (10) |
C10—C11—H11 | 119.1 | C32—C33—H33 | 126.5 |
C12—C11—H11 | 119.1 | C34—C33—H33 | 126.5 |
C13—C12—C11 | 118.8 (11) | C35—C34—C33 | 106.3 (10) |
C13—C12—H12 | 120.6 | C35—C34—H34 | 126.8 |
C11—C12—H12 | 120.6 | C33—C34—H34 | 126.8 |
C14—C13—C12 | 121.6 (10) | C34—C35—O5 | 112.0 (10) |
C14—C13—H13 | 119.2 | C34—C35—H35 | 124.0 |
C12—C13—H13 | 119.2 | O5—C35—H35 | 124.0 |
N5i—Cu1—N2—C2 | −23.6 (6) | C3—C10—C15—C14 | 175.2 (7) |
N5—Cu1—N2—C2 | 156.4 (6) | C13—C14—C15—C10 | 1.9 (14) |
O4—Cu1—N2—C2 | −113.1 (6) | C18—N3—C16—O3 | 178.2 (8) |
N5i—Cu1—N2—C1 | 137.0 (5) | C18—N3—C16—N4 | 0.3 (9) |
N5—Cu1—N2—C1 | −43.0 (5) | C17—N4—C16—O3 | −178.0 (8) |
O4—Cu1—N2—C1 | 47.5 (5) | C17—N4—C16—N3 | 0.1 (9) |
N2—Cu1—N5—C31 | −89.5 (6) | Cu1—O4—C17—N4 | 4.8 (12) |
N2i—Cu1—N5—C31 | 90.5 (6) | Cu1—O4—C17—C18 | −171.9 (5) |
O4—Cu1—N5—C31 | −171.4 (6) | C16—N4—C17—O4 | −177.7 (7) |
N5i—Cu1—O4—C17 | 123.5 (7) | C16—N4—C17—C18 | −0.4 (8) |
N5—Cu1—O4—C17 | −56.5 (7) | C16—N3—C18—C25 | −121.0 (7) |
N2—Cu1—O4—C17 | −147.6 (7) | C16—N3—C18—C17 | −0.6 (8) |
N2i—Cu1—O4—C17 | 32.4 (7) | C16—N3—C18—C19 | 112.6 (8) |
C3—N1—C1—O1 | 172.4 (7) | O4—C17—C18—N3 | 177.8 (7) |
C3—N1—C1—N2 | −9.0 (8) | N4—C17—C18—N3 | 0.5 (8) |
C2—N2—C1—O1 | −171.6 (7) | O4—C17—C18—C25 | −63.5 (9) |
Cu1—N2—C1—O1 | 23.8 (10) | N4—C17—C18—C25 | 119.2 (7) |
C2—N2—C1—N1 | 9.8 (8) | O4—C17—C18—C19 | 60.7 (10) |
Cu1—N2—C1—N1 | −154.9 (4) | N4—C17—C18—C19 | −116.6 (7) |
C1—N2—C2—O2 | 178.0 (7) | N3—C18—C19—C20 | −18.3 (11) |
Cu1—N2—C2—O2 | −19.0 (11) | C25—C18—C19—C20 | −144.2 (8) |
C1—N2—C2—C3 | −6.8 (8) | C17—C18—C19—C20 | 90.8 (9) |
Cu1—N2—C2—C3 | 156.2 (5) | N3—C18—C19—C24 | 166.9 (7) |
C1—N1—C3—C10 | −115.0 (7) | C25—C18—C19—C24 | 41.1 (9) |
C1—N1—C3—C4 | 118.9 (7) | C17—C18—C19—C24 | −83.9 (9) |
C1—N1—C3—C2 | 4.3 (7) | C24—C19—C20—C21 | −1.6 (13) |
O2—C2—C3—N1 | 177.2 (7) | C18—C19—C20—C21 | −176.4 (8) |
N2—C2—C3—N1 | 1.8 (7) | C19—C20—C21—C22 | 2.9 (14) |
O2—C2—C3—C10 | −67.1 (9) | C20—C21—C22—C23 | −2.9 (15) |
N2—C2—C3—C10 | 117.5 (6) | C21—C22—C23—C24 | 1.8 (15) |
O2—C2—C3—C4 | 58.6 (9) | C22—C23—C24—C19 | −0.5 (14) |
N2—C2—C3—C4 | −116.8 (6) | C20—C19—C24—C23 | 0.4 (12) |
N1—C3—C4—C9 | 168.1 (7) | C18—C19—C24—C23 | 175.4 (7) |
C10—C3—C4—C9 | 43.5 (10) | N3—C18—C25—C30 | 126.5 (8) |
C2—C3—C4—C9 | −83.2 (8) | C17—C18—C25—C30 | 14.1 (10) |
N1—C3—C4—C5 | −13.2 (10) | C19—C18—C25—C30 | −107.2 (8) |
C10—C3—C4—C5 | −137.7 (8) | N3—C18—C25—C26 | −53.8 (9) |
C2—C3—C4—C5 | 95.5 (8) | C17—C18—C25—C26 | −166.2 (6) |
C9—C4—C5—C6 | −0.2 (12) | C19—C18—C25—C26 | 72.5 (8) |
C3—C4—C5—C6 | −179.0 (8) | C30—C25—C26—C27 | −0.1 (12) |
C4—C5—C6—C7 | 0.4 (14) | C18—C25—C26—C27 | −179.9 (7) |
C5—C6—C7—C8 | 0.6 (15) | C25—C26—C27—C28 | 0.2 (13) |
C6—C7—C8—C9 | −1.6 (15) | C26—C27—C28—C29 | −0.1 (14) |
C5—C4—C9—C8 | −0.8 (12) | C27—C28—C29—C30 | −0.2 (14) |
C3—C4—C9—C8 | 178.0 (8) | C26—C25—C30—C29 | −0.1 (12) |
C7—C8—C9—C4 | 1.7 (14) | C18—C25—C30—C29 | 179.6 (7) |
N1—C3—C10—C15 | −66.2 (8) | C28—C29—C30—C25 | 0.3 (14) |
C4—C3—C10—C15 | 60.7 (9) | Cu1—N5—C31—C32 | −171.2 (6) |
C2—C3—C10—C15 | −175.5 (6) | C35—O5—C32—C33 | 0.3 (11) |
N1—C3—C10—C11 | 110.4 (8) | C35—O5—C32—C31 | 174.4 (8) |
C4—C3—C10—C11 | −122.7 (8) | N5—C31—C32—C33 | 105.6 (13) |
C2—C3—C10—C11 | 1.0 (10) | N5—C31—C32—O5 | −66.7 (11) |
C15—C10—C11—C12 | 0.1 (13) | O5—C32—C33—C34 | −0.6 (12) |
C3—C10—C11—C12 | −176.5 (8) | C31—C32—C33—C34 | −173.4 (10) |
C10—C11—C12—C13 | 1.2 (14) | C32—C33—C34—C35 | 0.6 (13) |
C11—C12—C13—C14 | −0.9 (15) | C33—C34—C35—O5 | −0.5 (14) |
C12—C13—C14—C15 | −0.6 (15) | C32—O5—C35—C34 | 0.1 (13) |
C11—C10—C15—C14 | −1.6 (12) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5A···O1 | 0.90 | 1.91 | 2.730 (8) | 151 |
N3—H3···O3ii | 0.86 | 1.97 | 2.817 (8) | 170 |
N5—H5B···O2i | 0.90 | 2.05 | 2.873 (8) | 152 |
N4—H4···O2i | 0.86 | 1.90 | 2.754 (8) | 171 |
N1—H1···O1iii | 0.86 | 2.10 | 2.821 (8) | 140 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y, −z; (iii) −x, −y+1, −z+1. |
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