Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101012331/oa1117sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101012331/oa1117Isup2.hkl |
CCDC reference: 175062
For related literature, see: Alvarez-Larena, Brianso-Penalva & Piniella (1995); Antorini et al. (1983); Arıcı, Ercan, Atakol & Cakırer (1999); Ertan & Csoregh (1995); Medina et al. (2000); Uehara et al. (1999).
A solution of L-histidine (20 mmol) in 0.5M NaOH solution (vol?) and a 2M NaOH solution (vol?) were added dropwise to a suspension of 2,6-pyridinedicarbonyl dichloride (20 mmol) in CH2Cl2 (vol?) with stirring over 0.5 h, and then the mixture was stirred for an additional 3 h at room temperature. 6M HCl was added to the separated water phase until a pH of 4 was reached. CuSO4·5H2O (18 mmol) was added to the resultant reaction mixture. Compound (I) precipitated as blue crystals after several days. Crystals of (I) suitable for single-crystal X-ray analysis were obtained from a high-performance liquid chromatography purification on an ODS column (ODS is ?), followed by slow evaporation of the solvent at room temperature. Please define ODS, and provide missing volumes of reagents.
The H atoms of the H2O and COOH groups were not fixed because they could not be found from the difference Fourier map. All other H atoms were refined using a riding model, with Uiso(H) = 1.2Ueq(C).
Data collection: CrystalClear (Rigaku, 2001); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku, 2001); program(s) used to solve structure: SIR97 (Altomare, 1998); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
[CuH2O(C13H10N4O5)] | Dx = 1.725 Mg m−3 |
Mr = 383.81 | Mo Kα radiation, λ = 0.7107 Å |
Monoclinic, P21 | Cell parameters from 9082 reflections |
a = 15.983 (1) Å | θ = 3.1–27.5° |
b = 6.5095 (4) Å | µ = 1.52 mm−1 |
c = 29.068 (1) Å | T = 123 K |
β = 102.2801 (5)° | Plate, blue |
V = 2955.0 (3) Å3 | 0.2 × 0.2 × 0.1 mm |
Z = 8 |
Rigaku Mercury CCD area-detector diffractometer | 11052 reflections with F2 > 2σ(F2) |
Detector resolution: 7.32 pixels mm-1 | Rint = 0.076 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (Blessing, 1995) | h = −20→19 |
Tmin = 0.731, Tmax = 0.859 | k = −8→7 |
21831 measured reflections | l = −37→37 |
12299 independent reflections |
Refinement on F2 | Weighting scheme based on measured s.u.'s w = 1/σ2(Fo2) |
R[F2 > 2σ(F2)] = 0.032 | (Δ/σ)max = 0.001 |
wR(F2) = 0.074 | Δρmax = 0.90 e Å−3 |
S = 1.34 | Δρmin = −1.03 e Å−3 |
12299 reflections | Absolute structure: 5197 Friedel pairs (Flack, 1983) |
902 parameters | Absolute structure parameter: 0.015 (7) |
H-atom parameters constrained |
[CuH2O(C13H10N4O5)] | V = 2955.0 (3) Å3 |
Mr = 383.81 | Z = 8 |
Monoclinic, P21 | Mo Kα radiation |
a = 15.983 (1) Å | µ = 1.52 mm−1 |
b = 6.5095 (4) Å | T = 123 K |
c = 29.068 (1) Å | 0.2 × 0.2 × 0.1 mm |
β = 102.2801 (5)° |
Rigaku Mercury CCD area-detector diffractometer | 12299 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 11052 reflections with F2 > 2σ(F2) |
Tmin = 0.731, Tmax = 0.859 | Rint = 0.076 |
21831 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.074 | Δρmax = 0.90 e Å−3 |
S = 1.34 | Δρmin = −1.03 e Å−3 |
12299 reflections | Absolute structure: 5197 Friedel pairs (Flack, 1983) |
902 parameters | Absolute structure parameter: 0.015 (7) |
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 using reflections with F2 > -10.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). The refinements were performed by using Crystals for crystallographic refinements program. All calculations were performed using the CrystalStructure crystallographic software package. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.43081 (2) | 0.06196 (9) | 0.09286 (1) | 0.01431 (9) | |
Cu2 | 0.34920 (2) | 0.30055 (7) | 0.40252 (1) | 0.01451 (8) | |
Cu3 | 0.15413 (2) | 0.30124 (8) | 0.59784 (1) | 0.01438 (8) | |
Cu4 | 0.05818 (2) | −0.02717 (9) | 0.91237 (1) | 0.01572 (9) | |
O1 | 0.4033 (1) | 0.0706 (4) | 0.02019 (7) | 0.0171 (5) | |
O2 | 0.4694 (1) | 0.0818 (4) | −0.04060 (8) | 0.0189 (5) | |
O3 | 0.6335 (1) | −0.0404 (4) | 0.20011 (8) | 0.0235 (6) | |
O4 | 0.4446 (2) | −0.2760 (4) | 0.25307 (9) | 0.0313 (7) | |
O5 | 0.4513 (2) | −0.3827 (4) | 0.18127 (9) | 0.0364 (8) | |
O6 | 0.4229 (1) | 0.4218 (3) | 0.09466 (8) | 0.0172 (6) | |
O7 | 0.3901 (1) | 0.3174 (4) | 0.47506 (7) | 0.0176 (5) | |
O8 | 0.5116 (1) | 0.3157 (4) | 0.53063 (7) | 0.0194 (6) | |
O9 | 0.4463 (1) | 0.3606 (3) | 0.28488 (8) | 0.0195 (6) | |
O10 | 0.1985 (2) | 0.6975 (4) | 0.26435 (9) | 0.0323 (7) | |
O11 | 0.2932 (2) | 0.7406 (4) | 0.3303 (1) | 0.0394 (8) | |
O12 | 0.3423 (1) | −0.0487 (4) | 0.41197 (8) | 0.0195 (5) | |
O13 | 0.1135 (1) | 0.3248 (4) | 0.52531 (7) | 0.0178 (5) | |
O14 | −0.0077 (1) | 0.3302 (4) | 0.46963 (7) | 0.0196 (6) | |
O15 | 0.0583 (1) | 0.3989 (3) | 0.71444 (8) | 0.0209 (6) | |
O16 | 0.3093 (2) | 0.7021 (4) | 0.73136 (9) | 0.0311 (7) | |
O17 | 0.2092 (2) | 0.7383 (4) | 0.66695 (9) | 0.0383 (8) | |
O18 | 0.1557 (1) | −0.0448 (4) | 0.58705 (8) | 0.0206 (5) | |
O19 | 0.0858 (1) | −0.0456 (4) | 0.98501 (7) | 0.0175 (5) | |
O20 | 0.0207 (1) | −0.0895 (4) | 1.04550 (8) | 0.0195 (6) | |
O21 | −0.1465 (1) | −0.0556 (4) | 0.80300 (8) | 0.0262 (6) | |
O22 | 0.0509 (2) | −0.2372 (4) | 0.74557 (8) | 0.0320 (7) | |
O23 | 0.0520 (2) | −0.3737 (4) | 0.8152 (1) | 0.050 (1) | |
O24 | 0.0881 (1) | −0.3772 (4) | 0.90989 (8) | 0.0191 (6) | |
N1 | 0.5442 (2) | 0.0548 (5) | 0.0809 (1) | 0.0155 (6) | |
N2 | 0.4953 (2) | 0.0167 (4) | 0.1580 (1) | 0.0176 (8) | |
N4 | 0.3195 (2) | 0.0083 (4) | 0.1059 (1) | 0.0162 (7) | |
N3 | 0.1837 (2) | −0.0598 (5) | 0.10103 (9) | 0.0174 (7) | |
N5 | 0.4708 (1) | 0.3140 (4) | 0.40762 (9) | 0.0144 (6) | |
N6 | 0.3517 (2) | 0.3447 (4) | 0.33558 (9) | 0.0176 (7) | |
N7 | 0.0961 (2) | 0.3483 (4) | 0.40633 (9) | 0.0166 (7) | |
N8 | 0.2268 (1) | 0.3245 (4) | 0.39420 (9) | 0.0159 (6) | |
N9 | 0.0328 (1) | 0.3274 (4) | 0.59242 (9) | 0.0142 (6) | |
N10 | 0.1522 (2) | 0.3454 (4) | 0.66480 (9) | 0.0173 (7) | |
N11 | 0.4078 (1) | 0.3284 (4) | 0.59412 (9) | 0.0165 (7) | |
N12 | 0.2771 (1) | 0.3152 (4) | 0.60622 (8) | 0.0154 (6) | |
N13 | −0.0549 (2) | −0.0535 (5) | 0.92409 (9) | 0.0167 (7) | |
N14 | −0.0079 (2) | −0.0076 (4) | 0.8461 (1) | 0.0188 (7) | |
N15 | 0.3050 (2) | 0.0587 (5) | 0.9032 (1) | 0.0181 (6) | |
N16 | 0.1663 (2) | 0.0518 (5) | 0.8989 (1) | 0.0181 (7) | |
C1 | 0.4690 (2) | 0.0756 (5) | 0.0021 (1) | 0.0143 (7) | |
C2 | 0.5548 (2) | 0.0729 (6) | 0.0374 (1) | 0.0153 (7) | |
C3 | 0.6362 (2) | 0.0811 (5) | 0.0280 (1) | 0.0168 (8) | |
C4 | 0.7058 (2) | 0.0702 (6) | 0.0664 (1) | 0.0191 (8) | |
C5 | 0.6926 (2) | 0.0459 (6) | 0.1120 (1) | 0.0185 (8) | |
C6 | 0.6092 (2) | 0.0377 (5) | 0.1183 (1) | 0.0159 (8) | |
C7 | 0.5797 (2) | 0.0024 (4) | 0.1636 (1) | 0.0171 (8) | |
C8 | 0.4586 (2) | −0.0176 (5) | 0.1989 (1) | 0.0172 (7) | |
C9 | 0.4518 (2) | −0.2471 (5) | 0.2096 (1) | 0.0199 (8) | |
C10 | 0.3698 (2) | 0.0862 (5) | 0.1928 (1) | 0.0176 (7) | |
C11 | 0.3037 (2) | 0.0164 (4) | 0.1510 (1) | 0.0140 (8) | |
C12 | 0.2191 (2) | −0.0270 (6) | 0.1482 (1) | 0.0186 (7) | |
C13 | 0.2462 (2) | −0.0384 (6) | 0.0770 (1) | 0.0157 (7) | |
C14 | 0.4716 (2) | 0.3151 (5) | 0.4886 (1) | 0.0150 (7) | |
C15 | 0.5219 (2) | 0.3148 (5) | 0.4503 (1) | 0.0146 (7) | |
C16 | 0.6100 (2) | 0.3206 (5) | 0.4546 (1) | 0.0168 (7) | |
C17 | 0.6423 (2) | 0.3235 (5) | 0.4137 (1) | 0.0190 (8) | |
C18 | 0.5868 (2) | 0.3225 (5) | 0.3694 (1) | 0.0175 (8) | |
C19 | 0.4998 (2) | 0.3188 (5) | 0.3679 (1) | 0.0156 (7) | |
C20 | 0.4277 (2) | 0.3407 (4) | 0.3246 (1) | 0.0152 (8) | |
C21 | 0.2768 (2) | 0.3953 (5) | 0.2987 (1) | 0.0154 (8) | |
C22 | 0.2586 (2) | 0.6270 (6) | 0.2994 (1) | 0.0234 (9) | |
C23 | 0.1988 (2) | 0.2713 (5) | 0.3061 (1) | 0.0181 (8) | |
C24 | 0.1699 (2) | 0.3152 (5) | 0.3509 (1) | 0.0152 (7) | |
C25 | 0.0889 (2) | 0.3326 (5) | 0.3584 (1) | 0.0169 (8) | |
C26 | 0.1800 (2) | 0.3434 (4) | 0.4265 (1) | 0.0161 (8) | |
C27 | 0.0322 (2) | 0.3269 (5) | 0.5114 (1) | 0.0147 (7) | |
C28 | −0.0185 (2) | 0.3290 (5) | 0.5500 (1) | 0.0145 (7) | |
C29 | −0.1064 (2) | 0.3381 (4) | 0.5454 (1) | 0.0168 (8) | |
C30 | −0.1389 (2) | 0.3434 (4) | 0.5865 (1) | 0.0191 (8) | |
C31 | −0.0834 (2) | 0.3429 (5) | 0.6307 (1) | 0.0186 (8) | |
C32 | 0.0039 (2) | 0.3373 (4) | 0.6323 (1) | 0.0155 (8) | |
C33 | 0.0759 (2) | 0.3607 (4) | 0.6753 (1) | 0.0165 (8) | |
C34 | 0.2273 (2) | 0.3986 (5) | 0.7009 (1) | 0.0166 (8) | |
C35 | 0.2468 (2) | 0.6271 (5) | 0.6984 (1) | 0.0215 (9) | |
C36 | 0.3044 (2) | 0.2674 (5) | 0.6946 (1) | 0.0170 (8) | |
C37 | 0.3339 (2) | 0.3040 (5) | 0.6496 (1) | 0.0150 (7) | |
C38 | 0.4150 (2) | 0.3153 (5) | 0.6422 (1) | 0.0162 (7) | |
C39 | 0.3239 (2) | 0.3279 (5) | 0.5739 (1) | 0.0155 (7) | |
C40 | 0.0206 (2) | −0.0665 (5) | 1.0030 (1) | 0.0168 (8) | |
C41 | −0.0653 (2) | −0.0651 (5) | 0.9676 (1) | 0.0156 (8) | |
C42 | −0.1466 (2) | −0.0767 (5) | 0.9772 (1) | 0.0211 (9) | |
C43 | −0.2164 (2) | −0.0683 (5) | 0.9389 (1) | 0.0216 (9) | |
C44 | −0.2039 (2) | −0.0531 (6) | 0.8929 (1) | 0.0207 (8) | |
C45 | −0.1207 (2) | −0.0475 (5) | 0.8866 (1) | 0.0168 (8) | |
C46 | −0.0920 (2) | −0.0363 (5) | 0.8405 (1) | 0.0192 (8) | |
C47 | 0.0286 (2) | −0.0077 (5) | 0.8045 (1) | 0.0199 (8) | |
C48 | 0.0445 (2) | −0.2253 (5) | 0.7893 (1) | 0.0206 (8) | |
C49 | 0.1105 (2) | 0.1236 (5) | 0.8118 (1) | 0.0221 (8) | |
C50 | 0.1806 (2) | 0.0744 (6) | 0.8536 (1) | 0.0177 (7) | |
C51 | 0.2669 (2) | 0.0772 (6) | 0.8564 (1) | 0.0213 (8) | |
C52 | 0.2434 (2) | 0.0425 (5) | 0.9279 (1) | 0.0180 (8) | |
H1 | 0.6444 | 0.0926 | −0.0034 | 0.020* | |
H2 | 0.7625 | 0.0799 | 0.0614 | 0.024* | |
H3 | 0.7398 | 0.0359 | 0.1381 | 0.021* | |
H4 | 0.4956 | 0.0437 | 0.2252 | 0.020* | |
H5 | 0.3484 | 0.0590 | 0.2203 | 0.021* | |
H6 | 0.3773 | 0.2301 | 0.1899 | 0.021* | |
H7 | 0.1904 | −0.0338 | 0.1737 | 0.023* | |
H8 | 0.1255 | −0.0916 | 0.08791 | 0.021* | |
H9 | 0.2387 | −0.0544 | 0.0439 | 0.019* | |
H10 | 0.6474 | 0.3221 | 0.4848 | 0.020* | |
H11 | 0.7025 | 0.3265 | 0.4159 | 0.024* | |
H12 | 0.6082 | 0.3241 | 0.3413 | 0.022* | |
H13 | 0.2884 | 0.3602 | 0.2690 | 0.018* | |
H14 | 0.1524 | 0.2999 | 0.2806 | 0.021* | |
H15 | 0.2130 | 0.1295 | 0.3059 | 0.021* | |
H16 | 0.0373 | 0.3335 | 0.3351 | 0.020* | |
H17 | 0.0501 | 0.3604 | 0.42217 | 0.020* | |
H18 | 0.2025 | 0.3525 | 0.4594 | 0.019* | |
H19 | −0.1436 | 0.3407 | 0.5152 | 0.020* | |
H20 | −0.1991 | 0.3474 | 0.5844 | 0.023* | |
H21 | −0.1048 | 0.3464 | 0.6588 | 0.024* | |
H22 | 0.2156 | 0.3694 | 0.7309 | 0.020* | |
H23 | 0.3510 | 0.2965 | 0.7200 | 0.020* | |
H24 | 0.2892 | 0.1267 | 0.6955 | 0.020* | |
H25 | 0.4666 | 0.3142 | 0.6655 | 0.019* | |
H26 | 0.4539 | 0.3365 | 0.57825 | 0.020* | |
H27 | 0.3013 | 0.3356 | 0.5410 | 0.019* | |
H28 | −0.1544 | −0.0892 | 1.0086 | 0.024* | |
H29 | −0.2730 | −0.0738 | 0.9442 | 0.026* | |
H30 | −0.2511 | −0.0459 | 0.8668 | 0.023* | |
H31 | −0.0124 | 0.0531 | 0.7798 | 0.023* | |
H32 | 0.1337 | 0.1083 | 0.7845 | 0.026* | |
H33 | 0.0943 | 0.2627 | 0.8146 | 0.026* | |
H34 | 0.2952 | 0.0888 | 0.8309 | 0.026* | |
H35 | 0.3649 | 0.0577 | 0.9160 | 0.022* | |
H36 | 0.2530 | 0.0272 | 0.9611 | 0.021* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0096 (2) | 0.0199 (2) | 0.0130 (2) | −0.0002 (2) | 0.0015 (1) | 0.0014 (2) |
Cu2 | 0.0093 (2) | 0.0225 (2) | 0.0117 (2) | 0.0001 (1) | 0.0022 (1) | 0.0009 (1) |
Cu3 | 0.0090 (2) | 0.0226 (2) | 0.0116 (2) | 0.0001 (1) | 0.0022 (1) | −0.0014 (1) |
Cu4 | 0.0119 (2) | 0.0206 (2) | 0.0136 (2) | 0.0015 (2) | 0.0004 (1) | −0.0011 (2) |
O1 | 0.013 (1) | 0.025 (1) | 0.014 (1) | 0.001 (1) | 0.0046 (8) | 0.001 (1) |
O2 | 0.018 (1) | 0.023 (1) | 0.017 (1) | 0.002 (1) | 0.0054 (9) | −0.001 (1) |
O3 | 0.018 (1) | 0.032 (1) | 0.018 (1) | 0.004 (1) | −0.0029 (9) | 0.001 (1) |
O4 | 0.053 (2) | 0.026 (1) | 0.017 (1) | −0.003 (1) | 0.013 (1) | 0.002 (1) |
O5 | 0.068 (2) | 0.022 (1) | 0.021 (1) | −0.006 (1) | 0.014 (1) | −0.002 (1) |
O6 | 0.015 (1) | 0.017 (1) | 0.021 (1) | −0.0001 (8) | 0.0051 (9) | −0.0001 (9) |
O7 | 0.0090 (9) | 0.029 (1) | 0.015 (1) | −0.0017 (9) | 0.0021 (8) | −0.002 (1) |
O8 | 0.014 (1) | 0.028 (1) | 0.015 (1) | −0.003 (1) | 0.0014 (8) | −0.002 (1) |
O9 | 0.023 (1) | 0.021 (1) | 0.016 (1) | −0.0013 (8) | 0.0079 (9) | 0.0008 (8) |
O10 | 0.038 (2) | 0.023 (1) | 0.030 (1) | 0.006 (1) | −0.006 (1) | 0.002 (1) |
O11 | 0.055 (2) | 0.028 (2) | 0.028 (1) | −0.004 (1) | −0.005 (1) | −0.008 (1) |
O12 | 0.015 (1) | 0.022 (1) | 0.020 (1) | 0.0002 (9) | 0.0007 (9) | −0.001 (1) |
O13 | 0.010 (1) | 0.029 (1) | 0.014 (1) | 0.0006 (9) | 0.0021 (8) | 0.0001 (9) |
O14 | 0.012 (1) | 0.030 (1) | 0.015 (1) | 0.0030 (9) | −0.0001 (9) | 0.0014 (9) |
O15 | 0.023 (1) | 0.025 (1) | 0.017 (1) | 0.0027 (9) | 0.0090 (9) | −0.0010 (9) |
O16 | 0.036 (1) | 0.021 (1) | 0.031 (1) | −0.007 (1) | −0.005 (1) | −0.002 (1) |
O17 | 0.051 (2) | 0.029 (1) | 0.028 (1) | 0.004 (1) | −0.007 (1) | 0.008 (1) |
O18 | 0.016 (1) | 0.023 (1) | 0.021 (1) | 0.001 (1) | 0.0000 (9) | −0.000 (1) |
O19 | 0.012 (1) | 0.025 (1) | 0.016 (1) | −0.002 (1) | 0.0034 (8) | −0.003 (1) |
O20 | 0.013 (1) | 0.030 (1) | 0.016 (1) | 0.0017 (9) | 0.0020 (9) | −0.0023 (9) |
O21 | 0.024 (1) | 0.033 (1) | 0.017 (1) | −0.001 (1) | −0.0050 (9) | −0.002 (1) |
O22 | 0.053 (2) | 0.029 (1) | 0.017 (1) | 0.004 (1) | 0.012 (1) | −0.001 (1) |
O23 | 0.109 (3) | 0.022 (1) | 0.024 (1) | 0.018 (2) | 0.024 (2) | 0.003 (1) |
O24 | 0.015 (1) | 0.023 (1) | 0.018 (1) | 0.0011 (9) | 0.0019 (9) | 0.0021 (9) |
N1 | 0.016 (1) | 0.013 (1) | 0.017 (1) | −0.002 (1) | 0.003 (1) | 0.000 (1) |
N2 | 0.016 (1) | 0.023 (2) | 0.012 (1) | −0.0006 (9) | −0.001 (1) | 0.0020 (9) |
N4 | 0.014 (1) | 0.018 (2) | 0.016 (1) | 0.0014 (9) | 0.002 (1) | −0.0013 (9) |
N3 | 0.014 (1) | 0.019 (2) | 0.020 (1) | −0.003 (1) | 0.004 (1) | −0.001 (1) |
N5 | 0.015 (1) | 0.013 (1) | 0.016 (1) | −0.002 (1) | 0.0044 (9) | 0.001 (1) |
N6 | 0.015 (1) | 0.026 (2) | 0.012 (1) | 0.002 (1) | 0.003 (1) | 0.002 (1) |
N7 | 0.012 (1) | 0.018 (2) | 0.019 (1) | 0.0015 (9) | 0.003 (1) | 0.001 (1) |
N8 | 0.015 (1) | 0.019 (1) | 0.013 (1) | 0.002 (1) | 0.003 (1) | 0.001 (1) |
N9 | 0.013 (1) | 0.014 (1) | 0.016 (1) | 0.001 (1) | 0.005 (1) | −0.001 (1) |
N10 | 0.013 (1) | 0.028 (2) | 0.012 (1) | −0.000 (1) | 0.003 (1) | −0.003 (1) |
N11 | 0.011 (1) | 0.020 (1) | 0.018 (1) | 0.000 (1) | 0.003 (1) | 0.000 (1) |
N12 | 0.013 (1) | 0.019 (1) | 0.014 (1) | −0.001 (1) | 0.003 (1) | −0.001 (1) |
N13 | 0.015 (1) | 0.015 (1) | 0.018 (1) | 0.002 (1) | −0.001 (1) | −0.007 (1) |
N14 | 0.023 (1) | 0.021 (2) | 0.011 (1) | 0.003 (1) | 0.000 (1) | −0.001 (1) |
N15 | 0.018 (1) | 0.017 (1) | 0.020 (1) | −0.002 (1) | 0.006 (1) | 0.002 (1) |
N16 | 0.019 (1) | 0.016 (1) | 0.018 (1) | 0.002 (1) | 0.001 (1) | 0.001 (1) |
C1 | 0.014 (1) | 0.011 (1) | 0.019 (1) | 0.002 (1) | 0.004 (1) | 0.000 (1) |
C2 | 0.016 (1) | 0.012 (1) | 0.018 (2) | −0.001 (1) | 0.003 (1) | −0.003 (1) |
C3 | 0.015 (1) | 0.013 (2) | 0.023 (2) | 0.001 (1) | 0.007 (1) | −0.002 (1) |
C4 | 0.012 (1) | 0.015 (1) | 0.032 (2) | 0.001 (1) | 0.009 (1) | −0.004 (2) |
C5 | 0.013 (1) | 0.014 (2) | 0.027 (2) | 0.001 (1) | −0.001 (1) | −0.003 (1) |
C6 | 0.015 (1) | 0.010 (2) | 0.022 (2) | 0.001 (1) | 0.000 (1) | −0.001 (1) |
C7 | 0.016 (1) | 0.016 (2) | 0.017 (2) | 0.001 (1) | −0.001 (1) | −0.001 (1) |
C8 | 0.016 (1) | 0.020 (2) | 0.014 (2) | −0.001 (1) | 0.001 (1) | −0.001 (1) |
C9 | 0.019 (2) | 0.026 (2) | 0.014 (1) | −0.001 (1) | 0.002 (1) | 0.001 (1) |
C10 | 0.019 (1) | 0.018 (2) | 0.016 (1) | −0.000 (1) | 0.003 (1) | 0.001 (1) |
C11 | 0.015 (1) | 0.012 (2) | 0.016 (2) | 0.001 (1) | 0.003 (1) | 0.001 (1) |
C12 | 0.019 (1) | 0.019 (1) | 0.019 (2) | 0.002 (1) | 0.006 (1) | 0.002 (1) |
C13 | 0.013 (1) | 0.019 (1) | 0.016 (1) | 0.001 (1) | 0.004 (1) | 0.001 (1) |
C14 | 0.012 (1) | 0.017 (1) | 0.016 (1) | −0.001 (1) | 0.003 (1) | −0.001 (1) |
C15 | 0.013 (1) | 0.013 (1) | 0.018 (1) | −0.002 (1) | 0.003 (1) | 0.000 (1) |
C16 | 0.012 (1) | 0.015 (2) | 0.023 (2) | −0.001 (1) | 0.001 (1) | 0.001 (1) |
C17 | 0.013 (1) | 0.017 (2) | 0.029 (2) | −0.002 (1) | 0.008 (1) | −0.002 (1) |
C18 | 0.020 (2) | 0.013 (2) | 0.022 (2) | −0.000 (1) | 0.011 (1) | 0.001 (1) |
C19 | 0.017 (1) | 0.014 (1) | 0.017 (1) | 0.001 (1) | 0.007 (1) | 0.003 (1) |
C20 | 0.017 (1) | 0.011 (2) | 0.018 (2) | −0.000 (1) | 0.005 (1) | 0.001 (1) |
C21 | 0.015 (1) | 0.020 (2) | 0.011 (1) | 0.001 (1) | 0.000 (1) | −0.001 (1) |
C22 | 0.026 (2) | 0.024 (2) | 0.017 (2) | −0.000 (1) | −0.001 (1) | −0.001 (1) |
C23 | 0.018 (1) | 0.018 (2) | 0.017 (2) | 0.001 (1) | 0.002 (1) | −0.001 (1) |
C24 | 0.013 (1) | 0.016 (1) | 0.016 (1) | 0.002 (1) | 0.001 (1) | 0.002 (1) |
C25 | 0.013 (1) | 0.017 (2) | 0.019 (2) | 0.002 (1) | 0.000 (1) | −0.000 (1) |
C26 | 0.010 (1) | 0.017 (2) | 0.020 (2) | 0.003 (1) | 0.002 (1) | 0.000 (1) |
C27 | 0.010 (1) | 0.017 (2) | 0.017 (2) | 0.002 (1) | 0.003 (1) | 0.001 (1) |
C28 | 0.013 (1) | 0.012 (2) | 0.018 (2) | 0.002 (1) | 0.003 (1) | −0.001 (1) |
C29 | 0.012 (1) | 0.016 (2) | 0.021 (2) | 0.001 (1) | 0.002 (1) | 0.000 (1) |
C30 | 0.012 (1) | 0.019 (2) | 0.028 (2) | 0.002 (1) | 0.008 (1) | 0.001 (1) |
C31 | 0.018 (2) | 0.017 (2) | 0.024 (2) | 0.000 (1) | 0.011 (1) | −0.002 (1) |
C32 | 0.015 (1) | 0.015 (2) | 0.018 (2) | 0.001 (1) | 0.007 (1) | −0.001 (1) |
C33 | 0.020 (2) | 0.015 (2) | 0.016 (2) | 0.002 (1) | 0.006 (1) | −0.000 (1) |
C34 | 0.018 (1) | 0.019 (2) | 0.013 (2) | −0.001 (1) | 0.003 (1) | −0.000 (1) |
C35 | 0.025 (2) | 0.021 (2) | 0.019 (2) | 0.001 (1) | 0.004 (1) | −0.001 (1) |
C36 | 0.018 (1) | 0.018 (2) | 0.014 (1) | 0.001 (1) | 0.000 (1) | 0.001 (1) |
C37 | 0.013 (1) | 0.014 (1) | 0.016 (1) | −0.001 (1) | −0.000 (1) | −0.002 (1) |
C38 | 0.014 (1) | 0.015 (2) | 0.019 (2) | 0.000 (1) | 0.002 (1) | −0.000 (1) |
C39 | 0.011 (1) | 0.019 (2) | 0.017 (1) | −0.004 (1) | 0.004 (1) | −0.001 (1) |
C40 | 0.012 (1) | 0.017 (2) | 0.021 (2) | 0.000 (1) | 0.001 (1) | −0.005 (1) |
C41 | 0.013 (1) | 0.015 (2) | 0.018 (2) | 0.002 (1) | 0.001 (1) | −0.004 (1) |
C42 | 0.015 (1) | 0.023 (2) | 0.023 (2) | −0.002 (1) | 0.001 (1) | −0.005 (1) |
C43 | 0.011 (1) | 0.023 (2) | 0.030 (2) | −0.002 (1) | 0.003 (1) | −0.009 (1) |
C44 | 0.014 (1) | 0.014 (2) | 0.030 (2) | 0.002 (1) | −0.005 (1) | −0.007 (1) |
C45 | 0.017 (1) | 0.011 (2) | 0.020 (2) | 0.000 (1) | −0.002 (1) | −0.003 (1) |
C46 | 0.021 (2) | 0.014 (1) | 0.019 (2) | 0.004 (1) | −0.004 (1) | −0.002 (1) |
C47 | 0.021 (2) | 0.020 (2) | 0.017 (2) | 0.006 (1) | 0.001 (1) | −0.001 (1) |
C48 | 0.024 (2) | 0.022 (2) | 0.016 (1) | −0.000 (1) | 0.002 (1) | −0.001 (1) |
C49 | 0.027 (2) | 0.022 (2) | 0.017 (2) | 0.002 (1) | 0.003 (1) | 0.004 (1) |
C50 | 0.022 (2) | 0.014 (1) | 0.016 (2) | −0.002 (1) | 0.004 (1) | −0.001 (1) |
C51 | 0.025 (2) | 0.020 (2) | 0.020 (2) | −0.004 (1) | 0.008 (1) | 0.000 (2) |
C52 | 0.017 (2) | 0.016 (2) | 0.020 (2) | −0.001 (1) | 0.001 (1) | 0.000 (1) |
Cu1—O1 | 2.065 (2) | N16—C50 | 1.392 (4) |
Cu1—O6 | 2.347 (2) | N16—C52 | 1.338 (4) |
Cu1—N1 | 1.917 (3) | C1—C2 | 1.528 (4) |
Cu1—N2 | 1.976 (3) | C2—C3 | 1.388 (4) |
Cu1—N4 | 1.928 (3) | C3—C4 | 1.401 (4) |
Cu2—O7 | 2.073 (2) | C3—H1 | 0.95 |
Cu2—O12 | 2.296 (2) | C4—C5 | 1.395 (5) |
Cu2—N5 | 1.920 (2) | C4—H2 | 0.95 |
Cu2—N6 | 1.975 (3) | C5—C6 | 1.384 (4) |
Cu2—N8 | 1.926 (2) | C5—H3 | 0.95 |
Cu3—O13 | 2.076 (2) | C6—C7 | 1.508 (5) |
Cu3—O18 | 2.275 (3) | C8—C9 | 1.535 (5) |
Cu3—N9 | 1.920 (2) | C8—C10 | 1.549 (4) |
Cu3—N10 | 1.974 (3) | C8—H4 | 0.95 |
Cu3—N12 | 1.930 (2) | C10—C11 | 1.500 (4) |
Cu4—O19 | 2.067 (2) | C10—H5 | 0.95 |
Cu4—O24 | 2.333 (2) | C10—H6 | 0.95 |
Cu4—N13 | 1.917 (3) | C11—C12 | 1.368 (4) |
Cu4—N14 | 1.993 (3) | C12—H7 | 0.95 |
Cu4—N16 | 1.922 (3) | C13—H9 | 0.95 |
O1—C1 | 1.272 (3) | C14—C15 | 1.507 (4) |
O2—C1 | 1.243 (4) | C15—C16 | 1.386 (4) |
O3—C7 | 1.248 (4) | C16—C17 | 1.396 (4) |
O4—C9 | 1.306 (4) | C16—H10 | 0.95 |
O5—C9 | 1.206 (4) | C17—C18 | 1.399 (4) |
O7—C14 | 1.278 (3) | C17—H11 | 0.95 |
O8—C14 | 1.252 (3) | C18—C19 | 1.382 (4) |
O9—C20 | 1.259 (4) | C18—H12 | 0.95 |
O10—C22 | 1.324 (4) | C19—C20 | 1.521 (4) |
O11—C22 | 1.205 (4) | C21—C22 | 1.537 (5) |
O13—C27 | 1.276 (3) | C21—C23 | 1.538 (4) |
O14—C27 | 1.247 (4) | C21—H13 | 0.95 |
O15—C33 | 1.253 (4) | C23—C24 | 1.499 (4) |
O16—C35 | 1.321 (4) | C23—H14 | 0.95 |
O17—C35 | 1.220 (4) | C23—H15 | 0.95 |
O19—C40 | 1.269 (4) | C24—C25 | 1.362 (4) |
O20—C40 | 1.245 (4) | C25—H16 | 0.95 |
O21—C46 | 1.249 (4) | C26—H18 | 0.95 |
O22—C48 | 1.299 (4) | C27—C28 | 1.517 (4) |
O23—C48 | 1.215 (4) | C28—C29 | 1.384 (4) |
N1—C2 | 1.314 (4) | C29—C30 | 1.403 (4) |
N1—C6 | 1.341 (4) | C29—H19 | 0.95 |
N2—C7 | 1.326 (4) | C30—C31 | 1.397 (4) |
N2—C8 | 1.450 (4) | C30—H20 | 0.95 |
N4—C11 | 1.387 (4) | C31—C32 | 1.387 (4) |
N4—C13 | 1.323 (4) | C31—H21 | 0.95 |
N3—C12 | 1.385 (4) | C32—C33 | 1.517 (4) |
N3—C13 | 1.342 (4) | C34—C35 | 1.525 (5) |
N3—H8 | 0.95 | C34—C36 | 1.543 (4) |
N5—C15 | 1.331 (4) | C34—H22 | 0.95 |
N5—C19 | 1.332 (4) | C36—C37 | 1.500 (4) |
N6—C20 | 1.321 (4) | C36—H23 | 0.95 |
N6—C21 | 1.464 (4) | C36—H24 | 0.95 |
N7—C25 | 1.376 (4) | C37—C38 | 1.360 (4) |
N7—C26 | 1.344 (4) | C38—H25 | 0.95 |
N7—H17 | 0.95 | C39—H27 | 0.95 |
N8—C24 | 1.389 (4) | C40—C41 | 1.530 (4) |
N8—C26 | 1.326 (4) | C41—C42 | 1.388 (4) |
N9—C28 | 1.327 (4) | C42—C43 | 1.401 (4) |
N9—C32 | 1.337 (4) | C42—H28 | 0.95 |
N10—C33 | 1.322 (4) | C43—C44 | 1.398 (5) |
N10—C34 | 1.458 (4) | C43—H29 | 0.95 |
N11—C38 | 1.380 (4) | C44—C45 | 1.380 (4) |
N11—C39 | 1.346 (4) | C44—H30 | 0.95 |
N11—H26 | 0.95 | C45—C46 | 1.506 (4) |
N12—C37 | 1.391 (3) | C47—C48 | 1.521 (4) |
N12—C39 | 1.321 (4) | C47—C49 | 1.540 (5) |
N13—C41 | 1.312 (4) | C47—H31 | 0.95 |
N13—C45 | 1.345 (4) | C49—C50 | 1.501 (4) |
N14—C46 | 1.333 (4) | C49—H32 | 0.95 |
N14—C47 | 1.450 (4) | C49—H33 | 0.95 |
N15—C51 | 1.371 (4) | C50—C51 | 1.365 (4) |
N15—C52 | 1.341 (4) | C51—H34 | 0.95 |
N15—H35 | 0.95 | C52—H36 | 0.95 |
Cu4···O20i | 3.444 (2) | N3···C43x | 3.582 (5) |
O1···N15ii | 3.431 (4) | N3···C43vii | 3.481 (4) |
O1···C3iii | 3.484 (4) | N3···C44x | 3.228 (5) |
O1···C52ii | 3.294 (4) | N3···C44vii | 3.315 (5) |
O2···O6iii | 2.770 (3) | N3···C45x | 3.373 (4) |
O2···N1iv | 3.285 (4) | N3···C45vii | 3.524 (5) |
O2···N15ii | 2.788 (4) | N3···H30x | 3.41 |
O2···C1iii | 3.551 (4) | N3···H30vii | 3.58 |
O2···C1iv | 3.476 (4) | N7···C29x | 3.596 (4) |
O2···C2iii | 3.339 (5) | N7···C29vii | 3.474 (4) |
O2···C2iv | 3.224 (5) | N7···C30x | 3.354 (4) |
O2···C52ii | 3.542 (4) | N7···C30vii | 3.292 (4) |
O3···O16v | 2.553 (3) | N7···C31x | 3.454 (4) |
O3···C34v | 3.265 (4) | N7···C31vii | 3.387 (4) |
O3···C35v | 3.338 (4) | N8···C30x | 3.525 (4) |
O3···C36v | 3.260 (4) | N8···H20x | 3.22 |
O3···C51v | 3.541 (4) | N8···H20vii | 3.51 |
O4···O9vi | 2.538 (3) | N9···H17x | 3.31 |
O4···C20vi | 3.296 (4) | N11···C16v | 3.584 (4) |
O4···C22vi | 3.571 (4) | N11···C16viii | 3.490 (4) |
O4···C38v | 3.428 (4) | N11···C17v | 3.379 (4) |
O5···O6vi | 2.771 (3) | N11···C17viii | 3.317 (4) |
O5···O9vi | 3.460 (3) | N11···C18v | 3.455 (4) |
O6···C43vii | 3.236 (4) | N11···C18viii | 3.382 (4) |
O6···C44vii | 3.599 (4) | N11···C19viii | 3.591 (4) |
O8···O12viii | 2.712 (3) | N12···C17v | 3.543 (4) |
O8···C14v | 3.327 (4) | N15···C1xi | 3.456 (4) |
O8···C14viii | 3.319 (4) | N15···C4v | 3.316 (5) |
O8···C15v | 3.369 (4) | N15···C4viii | 3.459 (5) |
O8···C15viii | 3.358 (4) | N15···C5v | 3.368 (5) |
O9···C9ix | 3.376 (4) | N15···C5viii | 3.203 (5) |
O10···O21vii | 2.559 (3) | N15···C6viii | 3.514 (4) |
O10···C46vii | 3.507 (4) | C1···C1iii | 3.412 (5) |
O10···H7ix | 3.14 | C1···C1iv | 3.412 (5) |
O11···O12ix | 2.708 (3) | C1···C2iii | 3.462 (5) |
O12···C30x | 3.335 (4) | C1···C2iv | 3.429 (5) |
O14···O18vii | 2.704 (3) | C4···C52v | 3.525 (5) |
O14···C27x | 3.359 (4) | C4···C52viii | 3.176 (5) |
O14···C27vii | 3.317 (4) | C5···C51v | 3.212 (5) |
O14···C28x | 3.354 (4) | C6···C51v | 3.581 (5) |
O14···C28vii | 3.338 (4) | C11···C44vii | 3.341 (4) |
O15···O22ix | 2.548 (3) | C12···C44vii | 3.298 (5) |
O15···O23ix | 3.302 (3) | C12···C45vii | 3.544 (5) |
O15···C48ix | 3.313 (4) | C13···C43x | 3.499 (5) |
O16···C7viii | 3.444 (4) | C13···C43vii | 3.116 (5) |
O17···O18ix | 2.697 (3) | C13···C44x | 3.564 (5) |
O18···C17v | 3.344 (4) | C13···C44vii | 3.385 (5) |
O19···O20i | 3.443 (3) | C14···C14v | 3.406 (5) |
O19···N3xi | 3.403 (3) | C14···C14viii | 3.406 (5) |
O19···C13xi | 3.288 (4) | C16···C39v | 3.531 (4) |
O19···C41i | 3.461 (4) | C17···C39v | 3.278 (4) |
O19···C42i | 3.318 (4) | C17···C39viii | 3.335 (4) |
O20···O24i | 2.752 (3) | C18···C37viii | 3.469 (5) |
O20···N3xi | 2.763 (3) | C18···C38v | 3.318 (4) |
O20···N13xii | 3.162 (4) | C18···C38viii | 3.225 (4) |
O20···C13xi | 3.540 (3) | C19···C38v | 3.585 (5) |
O20···C40xii | 3.416 (4) | C19···C38viii | 3.544 (5) |
O20···C41xii | 3.218 (4) | C20···H25viii | 3.50 |
O20···C41i | 3.524 (4) | C24···C31x | 3.459 (4) |
O21···C21x | 3.250 (4) | C25···C30x | 3.577 (4) |
O21···C22x | 3.348 (4) | C25···C31x | 3.206 (4) |
O21···C23x | 3.301 (4) | C25···C31vii | 3.340 (4) |
O22···C25x | 3.386 (4) | C25···C32x | 3.583 (4) |
O22···C33vi | 3.395 (4) | C26···C29vii | 3.582 (4) |
O23···O24 | 2.692 (3) | C26···C30x | 3.325 (4) |
O23···C49vi | 3.411 (4) | C26···C30vii | 3.326 (4) |
O24···C4v | 3.236 (4) | C27···C27x | 3.435 (5) |
O24···C40xii | 3.581 (4) | C27···C27vii | 3.435 (5) |
O24···C42xii | 3.468 (4) | C40···C40xii | 3.318 (5) |
N4···C43vii | 3.330 (4) | C40···C40i | 3.318 (5) |
N4···C44vii | 3.405 (4) | C40···C41xii | 3.393 (4) |
N3···C40ii | 3.429 (4) | C40···C41i | 3.411 (4) |
O1—Cu1—O6 | 89.71 (9) | N3—C13—H9 | 125 |
O1—Cu1—N1 | 79.5 (1) | O7—C14—O8 | 125.2 (3) |
O6—Cu1—N1 | 94.95 (11) | O7—C14—C15 | 116.2 (2) |
O1—Cu1—N2 | 159.8 (1) | O8—C14—C15 | 118.7 (3) |
O6—Cu1—N2 | 98.45 (9) | N5—C15—C14 | 111.8 (2) |
N1—Cu1—N2 | 81.36 (12) | N5—C15—C16 | 119.7 (3) |
O1—Cu1—N4 | 101.62 (11) | C14—C15—C16 | 128.5 (3) |
O6—Cu1—N4 | 96.87 (9) | C15—C16—C17 | 118.4 (3) |
N1—Cu1—N4 | 168.13 (12) | C15—C16—H10 | 121 |
N2—Cu1—N4 | 95.74 (12) | C17—C16—H10 | 121 |
O7—Cu2—O12 | 86.75 (8) | C16—C17—C18 | 120.4 (3) |
O7—Cu2—N5 | 79.86 (9) | C16—C17—H11 | 120 |
O12—Cu2—N5 | 96.3 (1) | C18—C17—H11 | 120 |
O7—Cu2—N6 | 157.80 (9) | C17—C18—C19 | 117.8 (3) |
O12—Cu2—N6 | 105.88 (9) | C17—C18—H12 | 121 |
N5—Cu2—N6 | 80.6 (1) | C19—C18—H12 | 121 |
O7—Cu2—N8 | 102.45 (9) | N5—C19—C18 | 120.4 (3) |
O12—Cu2—N8 | 91.3 (1) | N5—C19—C20 | 112.2 (3) |
N5—Cu2—N8 | 172.25 (12) | C18—C19—C20 | 127.1 (3) |
N6—Cu2—N8 | 95.6 (1) | O9—C20—N6 | 128.9 (3) |
O13—Cu3—O18 | 86.75 (8) | O9—C20—C19 | 119.0 (3) |
O13—Cu3—N9 | 79.48 (9) | N6—C20—C19 | 112.1 (3) |
O18—Cu3—N9 | 96.72 (9) | N6—C21—C22 | 109.8 (2) |
O13—Cu3—N10 | 157.44 (9) | N6—C21—C23 | 109.9 (3) |
O18—Cu3—N10 | 106.43 (9) | C22—C21—C23 | 110.7 (3) |
N9—Cu3—N10 | 80.8 (1) | N6—C21—H13 | 109 |
O13—Cu3—N12 | 102.43 (9) | C22—C21—H13 | 109 |
O18—Cu3—N12 | 91.3 (1) | C23—C21—H13 | 109 |
N9—Cu3—N12 | 171.83 (12) | O10—C22—O11 | 120.3 (3) |
N10—Cu3—N12 | 95.6 (1) | O10—C22—C21 | 116.1 (3) |
O19—Cu4—O24 | 88.53 (9) | O11—C22—C21 | 123.6 (3) |
O19—Cu4—N13 | 79.5 (1) | C21—C23—C24 | 115.5 (3) |
O24—Cu4—N13 | 97.2 (1) | C21—C23—H14 | 108 |
O19—Cu4—N14 | 160.9 (1) | C24—C23—H14 | 108 |
O24—Cu4—N14 | 95.9 (1) | C21—C23—H15 | 108 |
N13—Cu4—N14 | 81.47 (11) | C24—C23—H15 | 108 |
O19—Cu4—N16 | 102.61 (11) | H14—C23—H15 | 110 |
O24—Cu4—N16 | 93.19 (11) | N8—C24—C23 | 122.1 (3) |
N13—Cu4—N16 | 169.46 (13) | N8—C24—C25 | 108.2 (3) |
N14—Cu4—N16 | 95.74 (12) | C23—C24—C25 | 129.4 (3) |
Cu1—O1—C1 | 114.16 (19) | N7—C25—C24 | 106.9 (3) |
Cu2—O7—C14 | 113.16 (18) | N7—C25—H16 | 127 |
Cu3—O13—C27 | 113.56 (19) | C24—C25—H16 | 127 |
Cu4—O19—C40 | 114.27 (19) | N7—C26—N8 | 110.7 (3) |
Cu1—N1—C2 | 119.5 (2) | N7—C26—H18 | 125 |
Cu1—N1—C6 | 117.0 (2) | N8—C26—H18 | 125 |
C2—N1—C6 | 123.5 (3) | O13—C27—O14 | 125.7 (3) |
Cu1—N2—C7 | 116.0 (2) | O13—C27—C28 | 115.7 (3) |
Cu1—N2—C8 | 126.1 (2) | O14—C27—C28 | 118.6 (3) |
C7—N2—C8 | 117.8 (3) | N9—C28—C27 | 111.4 (2) |
Cu1—N4—C11 | 122.6 (2) | N9—C28—C29 | 120.3 (3) |
Cu1—N4—C13 | 130.3 (2) | C27—C28—C29 | 128.2 (3) |
C11—N4—C13 | 107.1 (3) | C28—C29—C30 | 118.0 (3) |
C12—N3—C13 | 107.8 (3) | C28—C29—H19 | 121 |
C12—N3—H8 | 126 | C30—C29—H19 | 121 |
C13—N3—H8 | 126 | C29—C30—C31 | 120.4 (3) |
Cu2—N5—C15 | 118.9 (2) | C29—C30—H20 | 120 |
Cu2—N5—C19 | 117.8 (2) | C31—C30—H20 | 120 |
C15—N5—C19 | 123.3 (3) | C30—C31—C32 | 117.9 (3) |
Cu2—N6—C20 | 116.6 (2) | C30—C31—H21 | 121 |
Cu2—N6—C21 | 124.7 (2) | C32—C31—H21 | 121 |
C20—N6—C21 | 118.6 (3) | N9—C32—C31 | 120.2 (3) |
C25—N7—C26 | 107.5 (3) | N9—C32—C33 | 112.2 (3) |
C25—N7—H17 | 126 | C31—C32—C33 | 127.3 (3) |
C26—N7—H17 | 126 | O15—C33—N10 | 128.5 (3) |
Cu2—N8—C24 | 124.2 (2) | O15—C33—C32 | 119.3 (3) |
Cu2—N8—C26 | 129.1 (2) | N10—C33—C32 | 112.1 (3) |
C24—N8—C26 | 106.7 (2) | N10—C34—C35 | 110.1 (3) |
Cu3—N9—C28 | 119.4 (2) | N10—C34—C36 | 109.8 (3) |
Cu3—N9—C32 | 117.5 (2) | C35—C34—C36 | 111.0 (3) |
C28—N9—C32 | 123.0 (3) | N10—C34—H22 | 109 |
Cu3—N10—C33 | 116.6 (2) | C35—C34—H22 | 109 |
Cu3—N10—C34 | 124.1 (2) | C36—C34—H22 | 109 |
C33—N10—C34 | 118.3 (3) | O16—C35—O17 | 120.0 (3) |
C38—N11—C39 | 107.6 (2) | O16—C35—C34 | 117.2 (3) |
C38—N11—H26 | 126 | O17—C35—C34 | 122.7 (3) |
C39—N11—H26 | 126 | C34—C36—C37 | 115.1 (3) |
Cu3—N12—C37 | 124.3 (2) | C34—C36—H23 | 108 |
Cu3—N12—C39 | 128.9 (2) | C37—C36—H23 | 108 |
C37—N12—C39 | 106.8 (2) | C34—C36—H24 | 108 |
Cu4—N13—C41 | 119.6 (2) | C37—C36—H24 | 108 |
Cu4—N13—C45 | 117.2 (2) | H23—C36—H24 | 110 |
C41—N13—C45 | 123.1 (3) | N12—C37—C36 | 122.2 (2) |
Cu4—N14—C46 | 115.0 (2) | N12—C37—C38 | 108.3 (3) |
Cu4—N14—C47 | 125.6 (2) | C36—C37—C38 | 129.3 (3) |
C46—N14—C47 | 118.2 (3) | N11—C38—C37 | 106.7 (3) |
C51—N15—C52 | 108.4 (3) | N11—C38—H25 | 127 |
C51—N15—H35 | 126 | C37—C38—H25 | 127 |
C52—N15—H35 | 126 | N11—C39—N12 | 110.7 (3) |
Cu4—N16—C50 | 123.9 (2) | N11—C39—H27 | 125 |
Cu4—N16—C52 | 127.4 (2) | N12—C39—H27 | 125 |
C50—N16—C52 | 106.7 (3) | O19—C40—O20 | 126.4 (3) |
O1—C1—O2 | 126.4 (3) | O19—C40—C41 | 114.9 (3) |
O1—C1—C2 | 115.0 (3) | O20—C40—C41 | 118.7 (3) |
O2—C1—C2 | 118.5 (2) | N13—C41—C40 | 111.7 (3) |
N1—C2—C1 | 111.5 (2) | N13—C41—C42 | 120.8 (3) |
N1—C2—C3 | 120.8 (3) | C40—C41—C42 | 127.5 (3) |
C1—C2—C3 | 127.7 (3) | C41—C42—C43 | 117.4 (3) |
C2—C3—C4 | 117.3 (3) | C41—C42—H28 | 121 |
C2—C3—H1 | 121 | C43—C42—H28 | 121 |
C4—C3—H1 | 121 | C42—C43—C44 | 120.8 (3) |
C3—C4—C5 | 120.6 (3) | C42—C43—H29 | 120 |
C3—C4—H2 | 120 | C44—C43—H29 | 120 |
C5—C4—H2 | 120 | C43—C44—C45 | 117.8 (3) |
C4—C5—C6 | 118.3 (3) | C43—C44—H30 | 121 |
C4—C5—H3 | 121 | C45—C44—H30 | 121 |
C6—C5—H3 | 121 | N13—C45—C44 | 120.0 (3) |
N1—C6—C5 | 119.5 (3) | N13—C45—C46 | 112.9 (3) |
N1—C6—C7 | 112.8 (3) | C44—C45—C46 | 127.1 (3) |
C5—C6—C7 | 127.7 (3) | O21—C46—N14 | 128.3 (3) |
O3—C7—N2 | 128.3 (3) | O21—C46—C45 | 118.9 (3) |
O3—C7—C6 | 119.2 (3) | N14—C46—C45 | 112.9 (3) |
N2—C7—C6 | 112.4 (3) | N14—C47—C48 | 111.4 (3) |
N2—C8—C9 | 112.0 (3) | N14—C47—C49 | 111.5 (3) |
N2—C8—C10 | 111.0 (3) | C48—C47—C49 | 111.5 (3) |
C9—C8—C10 | 110.2 (3) | N14—C47—H31 | 107 |
N2—C8—H4 | 108 | C48—C47—H31 | 107 |
C9—C8—H4 | 108 | C49—C47—H31 | 108 |
C10—C8—H4 | 108 | O22—C48—O23 | 122.8 (3) |
O4—C9—O5 | 124.5 (3) | O22—C48—C47 | 113.1 (3) |
O4—C9—C8 | 111.2 (3) | O23—C48—C47 | 124.1 (3) |
O5—C9—C8 | 124.3 (3) | C47—C49—C50 | 117.3 (3) |
C8—C10—C11 | 115.5 (3) | C47—C49—H32 | 107 |
C8—C10—H5 | 108 | C50—C49—H32 | 107 |
C11—C10—H5 | 108 | C47—C49—H33 | 108 |
C8—C10—H6 | 108 | C50—C49—H33 | 108 |
C11—C10—H6 | 108 | H32—C49—H33 | 110 |
H5—C10—H6 | 109 | N16—C50—C49 | 122.9 (3) |
N4—C11—C10 | 122.6 (3) | N16—C50—C51 | 108.1 (3) |
N4—C11—C12 | 108.3 (3) | C49—C50—C51 | 128.1 (3) |
C10—C11—C12 | 128.8 (3) | N15—C51—C50 | 106.8 (3) |
N3—C12—C11 | 106.3 (3) | N15—C51—H34 | 127 |
N3—C12—H7 | 127 | C50—C51—H34 | 127 |
C11—C12—H7 | 127 | N15—C52—N16 | 110.0 (3) |
N4—C13—N3 | 110.5 (3) | N15—C52—H36 | 125 |
N4—C13—H9 | 125 | N16—C52—H36 | 125 |
O6—Cu1—O1—C1 | 92.5 (4) | C25—N7—C26—N8 | −0.3 (5) |
N1—Cu1—O1—C1 | −2.6 (4) | Cu2—N8—C24—C23 | 4.1 (5) |
N2—Cu1—O1—C1 | −21.9 (5) | Cu2—N8—C24—C25 | 178.5 (2) |
N4—Cu1—O1—C1 | −170.6 (4) | C26—N8—C24—C23 | −173.4 (4) |
O1—Cu1—N1—C2 | 4.9 (4) | C26—N8—C24—C25 | 1.1 (5) |
O1—Cu1—N1—C6 | −177.2 (4) | Cu2—N8—C26—N7 | −177.8 (2) |
O6—Cu1—N1—C2 | −83.9 (5) | C24—N8—C26—N7 | −0.5 (5) |
O6—Cu1—N1—C6 | 94.0 (4) | Cu3—N9—C28—C27 | −4.9 (4) |
N2—Cu1—N1—C2 | 178.3 (5) | Cu3—N9—C28—C29 | 177.0 (3) |
N2—Cu1—N1—C6 | −3.8 (5) | C32—N9—C28—C27 | 177.1 (4) |
N4—Cu1—N1—C2 | 101.7 (6) | C32—N9—C28—C29 | −1.0 (6) |
N4—Cu1—N1—C6 | −80.3 (7) | Cu3—N9—C32—C31 | −175.8 (3) |
O1—Cu1—N2—C7 | 19.0 (4) | Cu3—N9—C32—C33 | 9.4 (4) |
O1—Cu1—N2—C8 | −156.0 (3) | C28—N9—C32—C31 | 2.2 (6) |
O6—Cu1—N2—C7 | −94.0 (4) | C28—N9—C32—C33 | −172.6 (4) |
O6—Cu1—N2—C8 | 91.1 (2) | Cu3—N10—C33—O15 | −176.0 (3) |
N1—Cu1—N2—C7 | −0.2 (2) | Cu3—N10—C33—C32 | 0.8 (4) |
N1—Cu1—N2—C8 | −175.1 (5) | C34—N10—C33—O15 | −7.0 (7) |
N4—Cu1—N2—C7 | 168.2 (4) | C34—N10—C33—C32 | 169.9 (4) |
N4—Cu1—N2—C8 | −6.7 (6) | Cu3—N10—C34—C35 | 79.4 (4) |
O1—Cu1—N4—C11 | −171.1 (4) | Cu3—N10—C34—C36 | −43.1 (4) |
O1—Cu1—N4—C13 | 8.1 (6) | C33—N10—C34—C35 | −88.8 (5) |
O6—Cu1—N4—C11 | −80.0 (2) | C33—N10—C34—C36 | 148.8 (4) |
O6—Cu1—N4—C13 | 99.2 (5) | C39—N11—C38—C37 | 0.9 (5) |
N1—Cu1—N4—C11 | 94.3 (6) | C38—N11—C39—N12 | −0.1 (5) |
N1—Cu1—N4—C13 | −86.5 (7) | Cu3—N12—C37—C36 | 3.6 (4) |
N2—Cu1—N4—C11 | 19.3 (2) | Cu3—N12—C37—C38 | 179.0 (2) |
N2—Cu1—N4—C13 | −161.5 (5) | C39—N12—C37—C36 | −173.9 (4) |
O12—Cu2—O7—C14 | 92.8 (4) | C39—N12—C37—C38 | 1.4 (5) |
N5—Cu2—O7—C14 | −4.1 (4) | Cu3—N12—C39—N11 | −178.2 (2) |
N6—Cu2—O7—C14 | −33.0 (4) | C37—N12—C39—N11 | −0.8 (5) |
N8—Cu2—O7—C14 | −176.6 (4) | Cu4—N13—C41—C40 | −3.1 (4) |
O7—Cu2—N5—C15 | 3.8 (4) | Cu4—N13—C41—C42 | 177.6 (3) |
O7—Cu2—N5—C19 | −177.2 (4) | C45—N13—C41—C40 | −179.2 (4) |
O12—Cu2—N5—C15 | −81.8 (4) | C45—N13—C41—C42 | 1.5 (7) |
O12—Cu2—N5—C19 | 97.2 (4) | Cu4—N13—C45—C44 | −176.1 (3) |
N6—Cu2—N5—C15 | 173.1 (4) | Cu4—N13—C45—C46 | 4.3 (4) |
N6—Cu2—N5—C19 | −7.9 (4) | C41—N13—C45—C44 | 0.1 (7) |
O7—Cu2—N6—C20 | 35.6 (4) | C41—N13—C45—C46 | −179.5 (4) |
O7—Cu2—N6—C21 | −139.8 (6) | Cu4—N14—C46—O21 | −171.1 (3) |
O12—Cu2—N6—C20 | −87.1 (4) | Cu4—N14—C46—C45 | 8.2 (4) |
O12—Cu2—N6—C21 | 97.4 (4) | C47—N14—C46—O21 | −3.3 (7) |
N5—Cu2—N6—C20 | 6.8 (4) | C47—N14—C46—C45 | 176.0 (4) |
N5—Cu2—N6—C21 | −168.7 (4) | Cu4—N14—C47—C48 | 84.1 (4) |
N8—Cu2—N6—C20 | 180.0 (4) | Cu4—N14—C47—C49 | −41.1 (4) |
N8—Cu2—N6—C21 | 4.5 (5) | C46—N14—C47—C48 | −82.2 (5) |
O7—Cu2—N8—C24 | −177.9 (4) | C46—N14—C47—C49 | 152.5 (4) |
O7—Cu2—N8—C26 | −1.1 (5) | C52—N15—C51—C50 | 0.7 (5) |
O12—Cu2—N8—C24 | −91.0 (4) | C51—N15—C52—N16 | −0.6 (6) |
O12—Cu2—N8—C26 | 85.9 (5) | Cu4—N16—C50—C49 | 25.4 (5) |
N6—Cu2—N8—C24 | 15.1 (5) | Cu4—N16—C50—C51 | −164.2 (2) |
N6—Cu2—N8—C26 | −168.0 (4) | C52—N16—C50—C49 | −170.1 (4) |
O18—Cu3—O13—C27 | 91.9 (4) | C52—N16—C50—C51 | 0.3 (5) |
N9—Cu3—O13—C27 | −5.6 (4) | Cu4—N16—C52—N15 | 164.0 (2) |
N10—Cu3—O13—C27 | −35.2 (4) | C50—N16—C52—N15 | 0.2 (5) |
N12—Cu3—O13—C27 | −177.5 (4) | O1—C1—C2—N1 | 3.4 (5) |
O13—Cu3—N9—C28 | 5.7 (4) | O1—C1—C2—C3 | −178.6 (4) |
O13—Cu3—N9—C32 | −176.2 (4) | O2—C1—C2—N1 | −176.5 (4) |
O18—Cu3—N9—C28 | −79.7 (4) | O2—C1—C2—C3 | 1.5 (7) |
O18—Cu3—N9—C32 | 98.4 (4) | N1—C2—C3—C4 | −0.3 (6) |
N10—Cu3—N9—C28 | 174.7 (4) | C1—C2—C3—C4 | −178.1 (4) |
N10—Cu3—N9—C32 | −7.2 (4) | C2—C3—C4—C5 | 1.8 (7) |
O13—Cu3—N10—C33 | 32.7 (4) | C3—C4—C5—C6 | −1.4 (7) |
O13—Cu3—N10—C34 | −135.7 (6) | C4—C5—C6—N1 | −0.6 (7) |
O18—Cu3—N10—C33 | −91.2 (4) | C4—C5—C6—C7 | 176.8 (4) |
O18—Cu3—N10—C34 | 100.5 (4) | N1—C6—C7—O3 | 171.6 (4) |
N9—Cu3—N10—C33 | 3.2 (4) | N1—C6—C7—N2 | −6.6 (6) |
N9—Cu3—N10—C34 | −165.2 (4) | C5—C6—C7—O3 | −5.9 (8) |
N12—Cu3—N10—C33 | 175.8 (4) | C5—C6—C7—N2 | 175.9 (5) |
N12—Cu3—N10—C34 | 7.4 (5) | N2—C8—C9—O4 | 160.2 (4) |
O13—Cu3—N12—C37 | −179.4 (4) | N2—C8—C9—O5 | −21.2 (6) |
O13—Cu3—N12—C39 | −2.5 (5) | C10—C8—C9—O4 | −75.7 (5) |
O18—Cu3—N12—C37 | −92.5 (4) | C10—C8—C9—O5 | 103.0 (5) |
O18—Cu3—N12—C39 | 84.5 (5) | N2—C8—C10—C11 | 59.0 (5) |
N10—Cu3—N12—C39 | −168.9 (4) | C9—C8—C10—C11 | −65.8 (5) |
O24—Cu4—O19—C40 | −96.9 (4) | C8—C10—C11—N4 | −50.3 (6) |
N13—Cu4—O19—C40 | 0.7 (4) | C8—C10—C11—C12 | 137.4 (5) |
N14—Cu4—O19—C40 | 6.8 (5) | N4—C11—C12—N3 | −0.5 (5) |
N16—Cu4—O19—C40 | 170.1 (4) | C10—C11—C12—N3 | 172.7 (4) |
O19—Cu4—N13—C41 | 1.6 (4) | O7—C14—C15—N5 | −0.9 (5) |
O19—Cu4—N13—C45 | 177.9 (4) | O7—C14—C15—C16 | 177.3 (4) |
O24—Cu4—N13—C41 | 88.7 (4) | O8—C14—C15—N5 | 179.9 (3) |
O24—Cu4—N13—C45 | −94.9 (4) | O8—C14—C15—C16 | −1.9 (6) |
N14—Cu4—N13—C41 | −176.4 (4) | N5—C15—C16—C17 | −0.6 (6) |
N14—Cu4—N13—C45 | −0.0 (5) | C14—C15—C16—C17 | −178.6 (4) |
N16—Cu4—N13—C41 | −100.8 (7) | C15—C16—C17—C18 | 0.6 (6) |
N16—Cu4—N13—C45 | 75.5 (7) | C16—C17—C18—C19 | 0.1 (6) |
O19—Cu4—N14—C46 | −11.1 (5) | C17—C18—C19—N5 | −0.8 (6) |
O19—Cu4—N14—C47 | −177.8 (3) | C17—C18—C19—C20 | 172.7 (4) |
O24—Cu4—N14—C46 | 91.6 (4) | N5—C19—C20—O9 | 175.5 (4) |
O24—Cu4—N14—C47 | −75.2 (2) | N5—C19—C20—N6 | −1.7 (5) |
N13—Cu4—N14—C46 | −4.9 (2) | C18—C19—C20—O9 | 1.6 (7) |
N13—Cu4—N14—C47 | −171.6 (5) | C18—C19—C20—N6 | −175.6 (4) |
N16—Cu4—N14—C46 | −174.6 (4) | N6—C21—C22—O10 | 172.6 (4) |
N16—Cu4—N14—C47 | 18.6 (6) | N6—C21—C22—O11 | −10.5 (6) |
O19—Cu4—N16—C50 | 176.9 (4) | C23—C21—C22—O10 | −65.9 (6) |
O19—Cu4—N16—C52 | 15.7 (6) | C23—C21—C22—O11 | 111.0 (5) |
O24—Cu4—N16—C50 | 87.7 (5) | N6—C21—C23—C24 | 63.1 (5) |
O24—Cu4—N16—C52 | −73.5 (5) | C22—C21—C23—C24 | −58.4 (6) |
N13—Cu4—N16—C50 | −82.8 (7) | C21—C23—C24—N8 | −47.2 (6) |
N13—Cu4—N16—C52 | 116.0 (6) | C21—C23—C24—C25 | 139.6 (5) |
N14—Cu4—N16—C50 | −8.5 (6) | N8—C24—C25—N7 | −1.2 (4) |
N14—Cu4—N16—C52 | −169.7 (5) | C23—C24—C25—N7 | 172.7 (4) |
Cu1—O1—C1—O2 | −179.8 (3) | O13—C27—C28—N9 | −0.2 (5) |
Cu1—O1—C1—C2 | 0.3 (4) | O13—C27—C28—C29 | 177.7 (4) |
Cu2—O7—C14—O8 | −177.1 (3) | O14—C27—C28—N9 | −179.3 (3) |
Cu2—O7—C14—C15 | 3.8 (4) | O14—C27—C28—C29 | −1.3 (6) |
Cu3—O13—C27—O14 | −176.4 (3) | N9—C28—C29—C30 | −0.6 (6) |
Cu3—O13—C27—C28 | 4.6 (4) | C27—C28—C29—C30 | −178.4 (4) |
Cu4—O19—C40—O20 | 176.8 (3) | C28—C29—C30—C31 | 1.0 (6) |
Cu4—O19—C40—C41 | −2.4 (4) | C29—C30—C31—C32 | 0.1 (6) |
Cu1—N1—C2—C1 | −5.9 (4) | C30—C31—C32—N9 | −1.7 (6) |
Cu1—N1—C2—C3 | 176.0 (3) | C30—C31—C32—C33 | 172.2 (4) |
C6—N1—C2—C1 | 176.4 (4) | N9—C32—C33—O15 | 170.8 (4) |
C6—N1—C2—C3 | −1.8 (7) | N9—C32—C33—N10 | −6.4 (5) |
Cu1—N1—C6—C5 | −175.6 (3) | C31—C32—C33—O15 | −3.6 (7) |
Cu1—N1—C6—C7 | 6.7 (4) | C31—C32—C33—N10 | 179.2 (4) |
C2—N1—C6—C5 | 2.2 (7) | N10—C34—C35—O16 | 174.9 (4) |
C2—N1—C6—C7 | −175.5 (4) | N10—C34—C35—O17 | −7.4 (6) |
Cu1—N2—C7—O3 | −174.3 (3) | C36—C34—C35—O16 | −63.3 (5) |
Cu1—N2—C7—C6 | 3.7 (4) | C36—C34—C35—O17 | 114.4 (5) |
C8—N2—C7—O3 | 1.0 (7) | N10—C34—C36—C37 | 64.3 (5) |
C8—N2—C7—C6 | 179.0 (4) | C35—C34—C36—C37 | −57.6 (5) |
Cu1—N2—C8—C9 | 95.6 (3) | C34—C36—C37—N12 | −46.2 (6) |
Cu1—N2—C8—C10 | −28.1 (4) | C34—C36—C37—C38 | 139.5 (5) |
C7—N2—C8—C9 | −79.2 (5) | N12—C37—C38—N11 | −1.5 (4) |
C7—N2—C8—C10 | 157.1 (4) | C36—C37—C38—N11 | 173.5 (4) |
Cu1—N4—C11—C10 | 5.8 (5) | O19—C40—C41—N13 | 3.6 (5) |
Cu1—N4—C11—C12 | 179.5 (2) | O19—C40—C41—C42 | −177.2 (4) |
C13—N4—C11—C10 | −173.6 (4) | O20—C40—C41—N13 | −175.7 (3) |
C13—N4—C11—C12 | 0.1 (5) | O20—C40—C41—C42 | 3.5 (6) |
Cu1—N4—C13—N3 | −179.0 (2) | N13—C41—C42—C43 | −2.1 (6) |
C11—N4—C13—N3 | 0.4 (5) | C40—C41—C42—C43 | 178.7 (4) |
C13—N3—C12—C11 | 0.7 (5) | C41—C42—C43—C44 | 1.3 (6) |
C12—N3—C13—N4 | −0.6 (5) | C42—C43—C44—C45 | 0.3 (7) |
Cu2—N5—C15—C14 | −2.8 (4) | C43—C44—C45—N13 | −1.0 (7) |
Cu2—N5—C15—C16 | 178.8 (3) | C43—C44—C45—C46 | 178.6 (4) |
C19—N5—C15—C14 | 178.2 (4) | N13—C45—C46—O21 | 171.2 (4) |
C19—N5—C15—C16 | −0.1 (6) | N13—C45—C46—N14 | −8.2 (6) |
Cu2—N5—C19—C18 | −178.1 (3) | C44—C45—C46—O21 | −8.4 (8) |
Cu2—N5—C19—C20 | 7.5 (4) | C44—C45—C46—N14 | 172.2 (5) |
C15—N5—C19—C18 | 0.8 (6) | N14—C47—C48—O22 | 159.5 (4) |
C15—N5—C19—C20 | −173.6 (4) | N14—C47—C48—O23 | −21.5 (6) |
Cu2—N6—C20—O9 | 178.6 (3) | C49—C47—C48—O22 | −75.3 (5) |
Cu2—N6—C20—C19 | −4.6 (4) | C49—C47—C48—O23 | 103.7 (5) |
C21—N6—C20—O9 | −5.7 (7) | N14—C47—C49—C50 | 54.5 (5) |
C21—N6—C20—C19 | 171.1 (4) | C48—C47—C49—C50 | −70.6 (5) |
Cu2—N6—C21—C22 | 82.2 (4) | C47—C49—C50—N16 | −49.5 (7) |
Cu2—N6—C21—C23 | −39.8 (4) | C47—C49—C50—C51 | 142.1 (5) |
C20—N6—C21—C22 | −93.2 (5) | N16—C50—C51—N15 | −0.6 (5) |
C20—N6—C21—C23 | 144.8 (4) | C49—C50—C51—N15 | 169.1 (4) |
C26—N7—C25—C24 | 0.9 (5) |
Symmetry codes: (i) −x, y+1/2, −z+2; (ii) x, y, z−1; (iii) −x+1, y−1/2, −z; (iv) −x+1, y+1/2, −z; (v) −x+1, y−1/2, −z+1; (vi) x, y−1, z; (vii) −x, y+1/2, −z+1; (viii) −x+1, y+1/2, −z+1; (ix) x, y+1, z; (x) −x, y−1/2, −z+1; (xi) x, y, z+1; (xii) −x, y−1/2, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H8···O20ii | 0.95 | 1.86 | 2.763 (3) | 159 |
N7—H17···O14 | 0.95 | 1.83 | 2.730 (3) | 158 |
N11—H26···O8 | 0.95 | 1.82 | 2.732 (3) | 159 |
N15—H35···O2xi | 0.95 | 1.87 | 2.788 (4) | 161 |
Symmetry codes: (ii) x, y, z−1; (xi) x, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | [CuH2O(C13H10N4O5)] |
Mr | 383.81 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 123 |
a, b, c (Å) | 15.983 (1), 6.5095 (4), 29.068 (1) |
β (°) | 102.2801 (5) |
V (Å3) | 2955.0 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.52 |
Crystal size (mm) | 0.2 × 0.2 × 0.1 |
Data collection | |
Diffractometer | Rigaku Mercury CCD area-detector diffractometer |
Absorption correction | Multi-scan (Blessing, 1995) |
Tmin, Tmax | 0.731, 0.859 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 21831, 12299, 11052 |
Rint | 0.076 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.074, 1.34 |
No. of reflections | 12299 |
No. of parameters | 902 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.90, −1.03 |
Absolute structure | 5197 Friedel pairs (Flack, 1983) |
Absolute structure parameter | 0.015 (7) |
Computer programs: CrystalClear (Rigaku, 2001), CrystalClear, CrystalStructure (Rigaku, 2001), SIR97 (Altomare, 1998), CRYSTALS (Watkin et al., 1996), ORTEP-3 (Farrugia, 1997), CrystalStructure.
Cu1—O1 | 2.065 (2) | Cu3—O13 | 2.076 (2) |
Cu1—O6 | 2.347 (2) | Cu3—O18 | 2.275 (3) |
Cu1—N1 | 1.917 (3) | Cu3—N9 | 1.920 (2) |
Cu1—N2 | 1.976 (3) | Cu3—N10 | 1.974 (3) |
Cu1—N4 | 1.928 (3) | Cu3—N12 | 1.930 (2) |
Cu2—O7 | 2.073 (2) | Cu4—O19 | 2.067 (2) |
Cu2—O12 | 2.296 (2) | Cu4—O24 | 2.333 (2) |
Cu2—N5 | 1.920 (2) | Cu4—N13 | 1.917 (3) |
Cu2—N6 | 1.975 (3) | Cu4—N14 | 1.993 (3) |
Cu2—N8 | 1.926 (2) | Cu4—N16 | 1.922 (3) |
O3···O16i | 2.553 (3) | O23···O24 | 2.692 (3) |
O4···O9ii | 2.538 (3) | ||
O1—Cu1—O6 | 89.71 (9) | O13—Cu3—O18 | 86.75 (8) |
O1—Cu1—N1 | 79.5 (1) | O13—Cu3—N9 | 79.48 (9) |
O6—Cu1—N1 | 94.95 (11) | O18—Cu3—N9 | 96.72 (9) |
O1—Cu1—N2 | 159.8 (1) | O13—Cu3—N10 | 157.44 (9) |
O6—Cu1—N2 | 98.45 (9) | O18—Cu3—N10 | 106.43 (9) |
N1—Cu1—N2 | 81.36 (12) | N9—Cu3—N10 | 80.8 (1) |
O1—Cu1—N4 | 101.62 (11) | O13—Cu3—N12 | 102.43 (9) |
O6—Cu1—N4 | 96.87 (9) | O18—Cu3—N12 | 91.3 (1) |
N1—Cu1—N4 | 168.13 (12) | N9—Cu3—N12 | 171.83 (12) |
N2—Cu1—N4 | 95.74 (12) | N10—Cu3—N12 | 95.6 (1) |
O7—Cu2—O12 | 86.75 (8) | O19—Cu4—O24 | 88.53 (9) |
O7—Cu2—N5 | 79.86 (9) | O19—Cu4—N13 | 79.5 (1) |
O12—Cu2—N5 | 96.3 (1) | O24—Cu4—N13 | 97.2 (1) |
O7—Cu2—N6 | 157.80 (9) | O19—Cu4—N14 | 160.9 (1) |
O12—Cu2—N6 | 105.88 (9) | O24—Cu4—N14 | 95.9 (1) |
N5—Cu2—N6 | 80.6 (1) | N13—Cu4—N14 | 81.47 (11) |
O7—Cu2—N8 | 102.45 (9) | O19—Cu4—N16 | 102.61 (11) |
O12—Cu2—N8 | 91.3 (1) | O24—Cu4—N16 | 93.19 (11) |
N5—Cu2—N8 | 172.25 (12) | N13—Cu4—N16 | 169.46 (13) |
N6—Cu2—N8 | 95.6 (1) | N14—Cu4—N16 | 95.74 (12) |
Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) x, y−1, z. |
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In the context of a study on the characteristic ligancy of asymmetric metal complexes, we have focused on the molecular and crystal structure of asymmetric copper(II) complexes. We report here the characteristic molecular conformation and crystal structure of the title compound, (I). \sch
The atoms and atom groups of the equatorial tetradentate ligand in (I) are almost coplanar, except for the methylene group, the inclined imidazole ring and the metal-free carboxyl group. The six-membered chelate ring formed by the imidazole ring and the amide group during the metal coordination of (I) has a twisted half-chair conformation, in accordance with the axial preference of the carboxyl substituent (Ertan & Csoregh, 1995; Uehara et al., 1999).
The apical water molecule has syn and anti coordination modes with respect to the axial carboxyl group. It is noteworthy that the unit cell consists of the isomers with a 1:3 ratio of syn to anti molecules (Fig. 2). The best mean basal plane of the first anti isomer, defined by O1, N1, N2 and N4, is planar to within 0.02 (3) Å, and atom Cu1 is displaced by 0.17 (3) Å toward the apical water molecule from this basal plane. For the Cu2 and Cu3 complexes, the corresponding values of the best mean basal plane are 0.04 (5) and 0.04 (5) Å, respectively, and the displacements of the Cu atoms are 0.16 (5) and 0.17 (5) Å, respectively.
The coordination geometry of the syn isomer around the Cu atom is almost the same as those of the anti isomers, except for the situation of the apical water molecule. The best mean basal plane of the syn isomer, defined by O19, N13, N14 and N16, is planar to within 0.06 (6) Å, and atom Cu4 is displaced by 0.12 (6) Å toward the apical water molecule. The equatorial conformation of the syn isomer is basically the same as those of the anti isomers, but with a somewhat different inclination angle between the imidazole ring and the basal plane. The inclined angle (25°) of the imidazole ring to the basal plane of the syn isomer is larger than those of the anti isomers, which are 3.6 (6)–5.7 (6)°.
The distances between each apical water molecule and the respective Cu atom of the anti isomers are 2.347 (2), 2.296 (2) and 2.275 (3) Å, and that of the syn isomer is 2.333 (2) Å. Those bond lengths are comparable with the corresponding distances in analogous pentacoordinated copper(II) complexes: 2.2681 (18) Å for the glycolato complex (Medina et al., 2000), 2.309 (3) Å for the propanediaminato complex (Arıcı et al., 1999), 2.355 (4) Å for the glycinate complex (Alvarez-Larena et al., 1995) and 2.294 (6) Å for the L-glutamate complex (Antorini et al., 1983).
The O23···O24 bond lengths indicate the existence of a significant OH···O hydrogen-bonding interaction between the apical water molecule and the carboxyl group in the syn isomer. Therefore, the O24—Cu4—N14 angle of the syn isomer [95.9 (1)°] is smaller than the corresponding angles of the anti isomers [98.45 (9)–106.43 (9)°].
The C═C distances in the oxalic acid moieties of the syn and anti isomers are in the range 1.507 (4)–1.520 (4) Å. These distances are similar to the value of 1.526 Å observed for the C═C distance in [Cu(C21H17N3O5)(H2O)] (ref?), in which the oxalic acid moieties coordinate to the CuII.
The O3···O16 and O4···O9 bond lengths are 2.553 (3) and 2.538 (3) Å, respectively. These distances indicate the existence of a significant OH···O hydrogen-bonding interaction between each anti isomer.