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The title compound, [Cu(C13H10N4O5)(H2O)], is an asymmetric and pentacoordinated square-pyramidal copper(II) complex, with a water mol­ecule occupying an apical position. It consists of syn and anti isomers of the apical water mol­ecule with respect to the metal-free carboxyl group on the equatorial ligand. The crystal structure of this complex is a rare example of conformational isomerization, in which the two isomers cocrystallize in a 1:3 ratio of syn to anti mol­ecules in the same lattice.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101012331/oa1117sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101012331/oa1117Isup2.hkl
Contains datablock I

CCDC reference: 175062

Comment top

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 CC 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 CC 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.

Related literature top

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).

Experimental top

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.

Refinement top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The molecular structure of the four isomers in (I), showing the atom-numbering scheme and with 30% probability displacement ellipsoids. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The packing of the molecules of (I).
(I) top
Crystal data top
[CuH2O(C13H10N4O5)]Dx = 1.725 Mg m3
Mr = 383.81Mo Kα radiation, λ = 0.7107 Å
Monoclinic, P21Cell parameters from 9082 reflections
a = 15.983 (1) Åθ = 3.1–27.5°
b = 6.5095 (4) ŵ = 1.52 mm1
c = 29.068 (1) ÅT = 123 K
β = 102.2801 (5)°Plate, blue
V = 2955.0 (3) Å30.2 × 0.2 × 0.1 mm
Z = 8
Data collection top
Rigaku Mercury CCD area-detector
diffractometer
11052 reflections with F2 > 2σ(F2)
Detector resolution: 7.32 pixels mm-1Rint = 0.076
ω scansθmax = 27.5°
Absorption correction: multi-scan
(Blessing, 1995)
h = 2019
Tmin = 0.731, Tmax = 0.859k = 87
21831 measured reflectionsl = 3737
12299 independent reflections
Refinement top
Refinement on F2Weighting scheme based on measured s.u.'s w = 1/σ2(Fo2)
R[F2 > 2σ(F2)] = 0.032(Δ/σ)max = 0.001
wR(F2) = 0.074Δρmax = 0.90 e Å3
S = 1.34Δρmin = 1.03 e Å3
12299 reflectionsAbsolute structure: 5197 Friedel pairs (Flack, 1983)
902 parametersAbsolute structure parameter: 0.015 (7)
H-atom parameters constrained
Crystal data top
[CuH2O(C13H10N4O5)]V = 2955.0 (3) Å3
Mr = 383.81Z = 8
Monoclinic, P21Mo Kα radiation
a = 15.983 (1) ŵ = 1.52 mm1
b = 6.5095 (4) ÅT = 123 K
c = 29.068 (1) Å0.2 × 0.2 × 0.1 mm
β = 102.2801 (5)°
Data collection top
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 = 0.859Rint = 0.076
21831 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.074Δρmax = 0.90 e Å3
S = 1.34Δρmin = 1.03 e Å3
12299 reflectionsAbsolute structure: 5197 Friedel pairs (Flack, 1983)
902 parametersAbsolute structure parameter: 0.015 (7)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cu10.43081 (2)0.06196 (9)0.09286 (1)0.01431 (9)
Cu20.34920 (2)0.30055 (7)0.40252 (1)0.01451 (8)
Cu30.15413 (2)0.30124 (8)0.59784 (1)0.01438 (8)
Cu40.05818 (2)0.02717 (9)0.91237 (1)0.01572 (9)
O10.4033 (1)0.0706 (4)0.02019 (7)0.0171 (5)
O20.4694 (1)0.0818 (4)0.04060 (8)0.0189 (5)
O30.6335 (1)0.0404 (4)0.20011 (8)0.0235 (6)
O40.4446 (2)0.2760 (4)0.25307 (9)0.0313 (7)
O50.4513 (2)0.3827 (4)0.18127 (9)0.0364 (8)
O60.4229 (1)0.4218 (3)0.09466 (8)0.0172 (6)
O70.3901 (1)0.3174 (4)0.47506 (7)0.0176 (5)
O80.5116 (1)0.3157 (4)0.53063 (7)0.0194 (6)
O90.4463 (1)0.3606 (3)0.28488 (8)0.0195 (6)
O100.1985 (2)0.6975 (4)0.26435 (9)0.0323 (7)
O110.2932 (2)0.7406 (4)0.3303 (1)0.0394 (8)
O120.3423 (1)0.0487 (4)0.41197 (8)0.0195 (5)
O130.1135 (1)0.3248 (4)0.52531 (7)0.0178 (5)
O140.0077 (1)0.3302 (4)0.46963 (7)0.0196 (6)
O150.0583 (1)0.3989 (3)0.71444 (8)0.0209 (6)
O160.3093 (2)0.7021 (4)0.73136 (9)0.0311 (7)
O170.2092 (2)0.7383 (4)0.66695 (9)0.0383 (8)
O180.1557 (1)0.0448 (4)0.58705 (8)0.0206 (5)
O190.0858 (1)0.0456 (4)0.98501 (7)0.0175 (5)
O200.0207 (1)0.0895 (4)1.04550 (8)0.0195 (6)
O210.1465 (1)0.0556 (4)0.80300 (8)0.0262 (6)
O220.0509 (2)0.2372 (4)0.74557 (8)0.0320 (7)
O230.0520 (2)0.3737 (4)0.8152 (1)0.050 (1)
O240.0881 (1)0.3772 (4)0.90989 (8)0.0191 (6)
N10.5442 (2)0.0548 (5)0.0809 (1)0.0155 (6)
N20.4953 (2)0.0167 (4)0.1580 (1)0.0176 (8)
N40.3195 (2)0.0083 (4)0.1059 (1)0.0162 (7)
N30.1837 (2)0.0598 (5)0.10103 (9)0.0174 (7)
N50.4708 (1)0.3140 (4)0.40762 (9)0.0144 (6)
N60.3517 (2)0.3447 (4)0.33558 (9)0.0176 (7)
N70.0961 (2)0.3483 (4)0.40633 (9)0.0166 (7)
N80.2268 (1)0.3245 (4)0.39420 (9)0.0159 (6)
N90.0328 (1)0.3274 (4)0.59242 (9)0.0142 (6)
N100.1522 (2)0.3454 (4)0.66480 (9)0.0173 (7)
N110.4078 (1)0.3284 (4)0.59412 (9)0.0165 (7)
N120.2771 (1)0.3152 (4)0.60622 (8)0.0154 (6)
N130.0549 (2)0.0535 (5)0.92409 (9)0.0167 (7)
N140.0079 (2)0.0076 (4)0.8461 (1)0.0188 (7)
N150.3050 (2)0.0587 (5)0.9032 (1)0.0181 (6)
N160.1663 (2)0.0518 (5)0.8989 (1)0.0181 (7)
C10.4690 (2)0.0756 (5)0.0021 (1)0.0143 (7)
C20.5548 (2)0.0729 (6)0.0374 (1)0.0153 (7)
C30.6362 (2)0.0811 (5)0.0280 (1)0.0168 (8)
C40.7058 (2)0.0702 (6)0.0664 (1)0.0191 (8)
C50.6926 (2)0.0459 (6)0.1120 (1)0.0185 (8)
C60.6092 (2)0.0377 (5)0.1183 (1)0.0159 (8)
C70.5797 (2)0.0024 (4)0.1636 (1)0.0171 (8)
C80.4586 (2)0.0176 (5)0.1989 (1)0.0172 (7)
C90.4518 (2)0.2471 (5)0.2096 (1)0.0199 (8)
C100.3698 (2)0.0862 (5)0.1928 (1)0.0176 (7)
C110.3037 (2)0.0164 (4)0.1510 (1)0.0140 (8)
C120.2191 (2)0.0270 (6)0.1482 (1)0.0186 (7)
C130.2462 (2)0.0384 (6)0.0770 (1)0.0157 (7)
C140.4716 (2)0.3151 (5)0.4886 (1)0.0150 (7)
C150.5219 (2)0.3148 (5)0.4503 (1)0.0146 (7)
C160.6100 (2)0.3206 (5)0.4546 (1)0.0168 (7)
C170.6423 (2)0.3235 (5)0.4137 (1)0.0190 (8)
C180.5868 (2)0.3225 (5)0.3694 (1)0.0175 (8)
C190.4998 (2)0.3188 (5)0.3679 (1)0.0156 (7)
C200.4277 (2)0.3407 (4)0.3246 (1)0.0152 (8)
C210.2768 (2)0.3953 (5)0.2987 (1)0.0154 (8)
C220.2586 (2)0.6270 (6)0.2994 (1)0.0234 (9)
C230.1988 (2)0.2713 (5)0.3061 (1)0.0181 (8)
C240.1699 (2)0.3152 (5)0.3509 (1)0.0152 (7)
C250.0889 (2)0.3326 (5)0.3584 (1)0.0169 (8)
C260.1800 (2)0.3434 (4)0.4265 (1)0.0161 (8)
C270.0322 (2)0.3269 (5)0.5114 (1)0.0147 (7)
C280.0185 (2)0.3290 (5)0.5500 (1)0.0145 (7)
C290.1064 (2)0.3381 (4)0.5454 (1)0.0168 (8)
C300.1389 (2)0.3434 (4)0.5865 (1)0.0191 (8)
C310.0834 (2)0.3429 (5)0.6307 (1)0.0186 (8)
C320.0039 (2)0.3373 (4)0.6323 (1)0.0155 (8)
C330.0759 (2)0.3607 (4)0.6753 (1)0.0165 (8)
C340.2273 (2)0.3986 (5)0.7009 (1)0.0166 (8)
C350.2468 (2)0.6271 (5)0.6984 (1)0.0215 (9)
C360.3044 (2)0.2674 (5)0.6946 (1)0.0170 (8)
C370.3339 (2)0.3040 (5)0.6496 (1)0.0150 (7)
C380.4150 (2)0.3153 (5)0.6422 (1)0.0162 (7)
C390.3239 (2)0.3279 (5)0.5739 (1)0.0155 (7)
C400.0206 (2)0.0665 (5)1.0030 (1)0.0168 (8)
C410.0653 (2)0.0651 (5)0.9676 (1)0.0156 (8)
C420.1466 (2)0.0767 (5)0.9772 (1)0.0211 (9)
C430.2164 (2)0.0683 (5)0.9389 (1)0.0216 (9)
C440.2039 (2)0.0531 (6)0.8929 (1)0.0207 (8)
C450.1207 (2)0.0475 (5)0.8866 (1)0.0168 (8)
C460.0920 (2)0.0363 (5)0.8405 (1)0.0192 (8)
C470.0286 (2)0.0077 (5)0.8045 (1)0.0199 (8)
C480.0445 (2)0.2253 (5)0.7893 (1)0.0206 (8)
C490.1105 (2)0.1236 (5)0.8118 (1)0.0221 (8)
C500.1806 (2)0.0744 (6)0.8536 (1)0.0177 (7)
C510.2669 (2)0.0772 (6)0.8564 (1)0.0213 (8)
C520.2434 (2)0.0425 (5)0.9279 (1)0.0180 (8)
H10.64440.09260.00340.020*
H20.76250.07990.06140.024*
H30.73980.03590.13810.021*
H40.49560.04370.22520.020*
H50.34840.05900.22030.021*
H60.37730.23010.18990.021*
H70.19040.03380.17370.023*
H80.12550.09160.087910.021*
H90.23870.05440.04390.019*
H100.64740.32210.48480.020*
H110.70250.32650.41590.024*
H120.60820.32410.34130.022*
H130.28840.36020.26900.018*
H140.15240.29990.28060.021*
H150.21300.12950.30590.021*
H160.03730.33350.33510.020*
H170.05010.36040.422170.020*
H180.20250.35250.45940.019*
H190.14360.34070.51520.020*
H200.19910.34740.58440.023*
H210.10480.34640.65880.024*
H220.21560.36940.73090.020*
H230.35100.29650.72000.020*
H240.28920.12670.69550.020*
H250.46660.31420.66550.019*
H260.45390.33650.578250.020*
H270.30130.33560.54100.019*
H280.15440.08921.00860.024*
H290.27300.07380.94420.026*
H300.25110.04590.86680.023*
H310.01240.05310.77980.023*
H320.13370.10830.78450.026*
H330.09430.26270.81460.026*
H340.29520.08880.83090.026*
H350.36490.05770.91600.022*
H360.25300.02720.96110.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0096 (2)0.0199 (2)0.0130 (2)0.0002 (2)0.0015 (1)0.0014 (2)
Cu20.0093 (2)0.0225 (2)0.0117 (2)0.0001 (1)0.0022 (1)0.0009 (1)
Cu30.0090 (2)0.0226 (2)0.0116 (2)0.0001 (1)0.0022 (1)0.0014 (1)
Cu40.0119 (2)0.0206 (2)0.0136 (2)0.0015 (2)0.0004 (1)0.0011 (2)
O10.013 (1)0.025 (1)0.014 (1)0.001 (1)0.0046 (8)0.001 (1)
O20.018 (1)0.023 (1)0.017 (1)0.002 (1)0.0054 (9)0.001 (1)
O30.018 (1)0.032 (1)0.018 (1)0.004 (1)0.0029 (9)0.001 (1)
O40.053 (2)0.026 (1)0.017 (1)0.003 (1)0.013 (1)0.002 (1)
O50.068 (2)0.022 (1)0.021 (1)0.006 (1)0.014 (1)0.002 (1)
O60.015 (1)0.017 (1)0.021 (1)0.0001 (8)0.0051 (9)0.0001 (9)
O70.0090 (9)0.029 (1)0.015 (1)0.0017 (9)0.0021 (8)0.002 (1)
O80.014 (1)0.028 (1)0.015 (1)0.003 (1)0.0014 (8)0.002 (1)
O90.023 (1)0.021 (1)0.016 (1)0.0013 (8)0.0079 (9)0.0008 (8)
O100.038 (2)0.023 (1)0.030 (1)0.006 (1)0.006 (1)0.002 (1)
O110.055 (2)0.028 (2)0.028 (1)0.004 (1)0.005 (1)0.008 (1)
O120.015 (1)0.022 (1)0.020 (1)0.0002 (9)0.0007 (9)0.001 (1)
O130.010 (1)0.029 (1)0.014 (1)0.0006 (9)0.0021 (8)0.0001 (9)
O140.012 (1)0.030 (1)0.015 (1)0.0030 (9)0.0001 (9)0.0014 (9)
O150.023 (1)0.025 (1)0.017 (1)0.0027 (9)0.0090 (9)0.0010 (9)
O160.036 (1)0.021 (1)0.031 (1)0.007 (1)0.005 (1)0.002 (1)
O170.051 (2)0.029 (1)0.028 (1)0.004 (1)0.007 (1)0.008 (1)
O180.016 (1)0.023 (1)0.021 (1)0.001 (1)0.0000 (9)0.000 (1)
O190.012 (1)0.025 (1)0.016 (1)0.002 (1)0.0034 (8)0.003 (1)
O200.013 (1)0.030 (1)0.016 (1)0.0017 (9)0.0020 (9)0.0023 (9)
O210.024 (1)0.033 (1)0.017 (1)0.001 (1)0.0050 (9)0.002 (1)
O220.053 (2)0.029 (1)0.017 (1)0.004 (1)0.012 (1)0.001 (1)
O230.109 (3)0.022 (1)0.024 (1)0.018 (2)0.024 (2)0.003 (1)
O240.015 (1)0.023 (1)0.018 (1)0.0011 (9)0.0019 (9)0.0021 (9)
N10.016 (1)0.013 (1)0.017 (1)0.002 (1)0.003 (1)0.000 (1)
N20.016 (1)0.023 (2)0.012 (1)0.0006 (9)0.001 (1)0.0020 (9)
N40.014 (1)0.018 (2)0.016 (1)0.0014 (9)0.002 (1)0.0013 (9)
N30.014 (1)0.019 (2)0.020 (1)0.003 (1)0.004 (1)0.001 (1)
N50.015 (1)0.013 (1)0.016 (1)0.002 (1)0.0044 (9)0.001 (1)
N60.015 (1)0.026 (2)0.012 (1)0.002 (1)0.003 (1)0.002 (1)
N70.012 (1)0.018 (2)0.019 (1)0.0015 (9)0.003 (1)0.001 (1)
N80.015 (1)0.019 (1)0.013 (1)0.002 (1)0.003 (1)0.001 (1)
N90.013 (1)0.014 (1)0.016 (1)0.001 (1)0.005 (1)0.001 (1)
N100.013 (1)0.028 (2)0.012 (1)0.000 (1)0.003 (1)0.003 (1)
N110.011 (1)0.020 (1)0.018 (1)0.000 (1)0.003 (1)0.000 (1)
N120.013 (1)0.019 (1)0.014 (1)0.001 (1)0.003 (1)0.001 (1)
N130.015 (1)0.015 (1)0.018 (1)0.002 (1)0.001 (1)0.007 (1)
N140.023 (1)0.021 (2)0.011 (1)0.003 (1)0.000 (1)0.001 (1)
N150.018 (1)0.017 (1)0.020 (1)0.002 (1)0.006 (1)0.002 (1)
N160.019 (1)0.016 (1)0.018 (1)0.002 (1)0.001 (1)0.001 (1)
C10.014 (1)0.011 (1)0.019 (1)0.002 (1)0.004 (1)0.000 (1)
C20.016 (1)0.012 (1)0.018 (2)0.001 (1)0.003 (1)0.003 (1)
C30.015 (1)0.013 (2)0.023 (2)0.001 (1)0.007 (1)0.002 (1)
C40.012 (1)0.015 (1)0.032 (2)0.001 (1)0.009 (1)0.004 (2)
C50.013 (1)0.014 (2)0.027 (2)0.001 (1)0.001 (1)0.003 (1)
C60.015 (1)0.010 (2)0.022 (2)0.001 (1)0.000 (1)0.001 (1)
C70.016 (1)0.016 (2)0.017 (2)0.001 (1)0.001 (1)0.001 (1)
C80.016 (1)0.020 (2)0.014 (2)0.001 (1)0.001 (1)0.001 (1)
C90.019 (2)0.026 (2)0.014 (1)0.001 (1)0.002 (1)0.001 (1)
C100.019 (1)0.018 (2)0.016 (1)0.000 (1)0.003 (1)0.001 (1)
C110.015 (1)0.012 (2)0.016 (2)0.001 (1)0.003 (1)0.001 (1)
C120.019 (1)0.019 (1)0.019 (2)0.002 (1)0.006 (1)0.002 (1)
C130.013 (1)0.019 (1)0.016 (1)0.001 (1)0.004 (1)0.001 (1)
C140.012 (1)0.017 (1)0.016 (1)0.001 (1)0.003 (1)0.001 (1)
C150.013 (1)0.013 (1)0.018 (1)0.002 (1)0.003 (1)0.000 (1)
C160.012 (1)0.015 (2)0.023 (2)0.001 (1)0.001 (1)0.001 (1)
C170.013 (1)0.017 (2)0.029 (2)0.002 (1)0.008 (1)0.002 (1)
C180.020 (2)0.013 (2)0.022 (2)0.000 (1)0.011 (1)0.001 (1)
C190.017 (1)0.014 (1)0.017 (1)0.001 (1)0.007 (1)0.003 (1)
C200.017 (1)0.011 (2)0.018 (2)0.000 (1)0.005 (1)0.001 (1)
C210.015 (1)0.020 (2)0.011 (1)0.001 (1)0.000 (1)0.001 (1)
C220.026 (2)0.024 (2)0.017 (2)0.000 (1)0.001 (1)0.001 (1)
C230.018 (1)0.018 (2)0.017 (2)0.001 (1)0.002 (1)0.001 (1)
C240.013 (1)0.016 (1)0.016 (1)0.002 (1)0.001 (1)0.002 (1)
C250.013 (1)0.017 (2)0.019 (2)0.002 (1)0.000 (1)0.000 (1)
C260.010 (1)0.017 (2)0.020 (2)0.003 (1)0.002 (1)0.000 (1)
C270.010 (1)0.017 (2)0.017 (2)0.002 (1)0.003 (1)0.001 (1)
C280.013 (1)0.012 (2)0.018 (2)0.002 (1)0.003 (1)0.001 (1)
C290.012 (1)0.016 (2)0.021 (2)0.001 (1)0.002 (1)0.000 (1)
C300.012 (1)0.019 (2)0.028 (2)0.002 (1)0.008 (1)0.001 (1)
C310.018 (2)0.017 (2)0.024 (2)0.000 (1)0.011 (1)0.002 (1)
C320.015 (1)0.015 (2)0.018 (2)0.001 (1)0.007 (1)0.001 (1)
C330.020 (2)0.015 (2)0.016 (2)0.002 (1)0.006 (1)0.000 (1)
C340.018 (1)0.019 (2)0.013 (2)0.001 (1)0.003 (1)0.000 (1)
C350.025 (2)0.021 (2)0.019 (2)0.001 (1)0.004 (1)0.001 (1)
C360.018 (1)0.018 (2)0.014 (1)0.001 (1)0.000 (1)0.001 (1)
C370.013 (1)0.014 (1)0.016 (1)0.001 (1)0.000 (1)0.002 (1)
C380.014 (1)0.015 (2)0.019 (2)0.000 (1)0.002 (1)0.000 (1)
C390.011 (1)0.019 (2)0.017 (1)0.004 (1)0.004 (1)0.001 (1)
C400.012 (1)0.017 (2)0.021 (2)0.000 (1)0.001 (1)0.005 (1)
C410.013 (1)0.015 (2)0.018 (2)0.002 (1)0.001 (1)0.004 (1)
C420.015 (1)0.023 (2)0.023 (2)0.002 (1)0.001 (1)0.005 (1)
C430.011 (1)0.023 (2)0.030 (2)0.002 (1)0.003 (1)0.009 (1)
C440.014 (1)0.014 (2)0.030 (2)0.002 (1)0.005 (1)0.007 (1)
C450.017 (1)0.011 (2)0.020 (2)0.000 (1)0.002 (1)0.003 (1)
C460.021 (2)0.014 (1)0.019 (2)0.004 (1)0.004 (1)0.002 (1)
C470.021 (2)0.020 (2)0.017 (2)0.006 (1)0.001 (1)0.001 (1)
C480.024 (2)0.022 (2)0.016 (1)0.000 (1)0.002 (1)0.001 (1)
C490.027 (2)0.022 (2)0.017 (2)0.002 (1)0.003 (1)0.004 (1)
C500.022 (2)0.014 (1)0.016 (2)0.002 (1)0.004 (1)0.001 (1)
C510.025 (2)0.020 (2)0.020 (2)0.004 (1)0.008 (1)0.000 (2)
C520.017 (2)0.016 (2)0.020 (2)0.001 (1)0.001 (1)0.000 (1)
Geometric parameters (Å, º) top
Cu1—O12.065 (2)N16—C501.392 (4)
Cu1—O62.347 (2)N16—C521.338 (4)
Cu1—N11.917 (3)C1—C21.528 (4)
Cu1—N21.976 (3)C2—C31.388 (4)
Cu1—N41.928 (3)C3—C41.401 (4)
Cu2—O72.073 (2)C3—H10.95
Cu2—O122.296 (2)C4—C51.395 (5)
Cu2—N51.920 (2)C4—H20.95
Cu2—N61.975 (3)C5—C61.384 (4)
Cu2—N81.926 (2)C5—H30.95
Cu3—O132.076 (2)C6—C71.508 (5)
Cu3—O182.275 (3)C8—C91.535 (5)
Cu3—N91.920 (2)C8—C101.549 (4)
Cu3—N101.974 (3)C8—H40.95
Cu3—N121.930 (2)C10—C111.500 (4)
Cu4—O192.067 (2)C10—H50.95
Cu4—O242.333 (2)C10—H60.95
Cu4—N131.917 (3)C11—C121.368 (4)
Cu4—N141.993 (3)C12—H70.95
Cu4—N161.922 (3)C13—H90.95
O1—C11.272 (3)C14—C151.507 (4)
O2—C11.243 (4)C15—C161.386 (4)
O3—C71.248 (4)C16—C171.396 (4)
O4—C91.306 (4)C16—H100.95
O5—C91.206 (4)C17—C181.399 (4)
O7—C141.278 (3)C17—H110.95
O8—C141.252 (3)C18—C191.382 (4)
O9—C201.259 (4)C18—H120.95
O10—C221.324 (4)C19—C201.521 (4)
O11—C221.205 (4)C21—C221.537 (5)
O13—C271.276 (3)C21—C231.538 (4)
O14—C271.247 (4)C21—H130.95
O15—C331.253 (4)C23—C241.499 (4)
O16—C351.321 (4)C23—H140.95
O17—C351.220 (4)C23—H150.95
O19—C401.269 (4)C24—C251.362 (4)
O20—C401.245 (4)C25—H160.95
O21—C461.249 (4)C26—H180.95
O22—C481.299 (4)C27—C281.517 (4)
O23—C481.215 (4)C28—C291.384 (4)
N1—C21.314 (4)C29—C301.403 (4)
N1—C61.341 (4)C29—H190.95
N2—C71.326 (4)C30—C311.397 (4)
N2—C81.450 (4)C30—H200.95
N4—C111.387 (4)C31—C321.387 (4)
N4—C131.323 (4)C31—H210.95
N3—C121.385 (4)C32—C331.517 (4)
N3—C131.342 (4)C34—C351.525 (5)
N3—H80.95C34—C361.543 (4)
N5—C151.331 (4)C34—H220.95
N5—C191.332 (4)C36—C371.500 (4)
N6—C201.321 (4)C36—H230.95
N6—C211.464 (4)C36—H240.95
N7—C251.376 (4)C37—C381.360 (4)
N7—C261.344 (4)C38—H250.95
N7—H170.95C39—H270.95
N8—C241.389 (4)C40—C411.530 (4)
N8—C261.326 (4)C41—C421.388 (4)
N9—C281.327 (4)C42—C431.401 (4)
N9—C321.337 (4)C42—H280.95
N10—C331.322 (4)C43—C441.398 (5)
N10—C341.458 (4)C43—H290.95
N11—C381.380 (4)C44—C451.380 (4)
N11—C391.346 (4)C44—H300.95
N11—H260.95C45—C461.506 (4)
N12—C371.391 (3)C47—C481.521 (4)
N12—C391.321 (4)C47—C491.540 (5)
N13—C411.312 (4)C47—H310.95
N13—C451.345 (4)C49—C501.501 (4)
N14—C461.333 (4)C49—H320.95
N14—C471.450 (4)C49—H330.95
N15—C511.371 (4)C50—C511.365 (4)
N15—C521.341 (4)C51—H340.95
N15—H350.95C52—H360.95
Cu4···O20i3.444 (2)N3···C43x3.582 (5)
O1···N15ii3.431 (4)N3···C43vii3.481 (4)
O1···C3iii3.484 (4)N3···C44x3.228 (5)
O1···C52ii3.294 (4)N3···C44vii3.315 (5)
O2···O6iii2.770 (3)N3···C45x3.373 (4)
O2···N1iv3.285 (4)N3···C45vii3.524 (5)
O2···N15ii2.788 (4)N3···H30x3.41
O2···C1iii3.551 (4)N3···H30vii3.58
O2···C1iv3.476 (4)N7···C29x3.596 (4)
O2···C2iii3.339 (5)N7···C29vii3.474 (4)
O2···C2iv3.224 (5)N7···C30x3.354 (4)
O2···C52ii3.542 (4)N7···C30vii3.292 (4)
O3···O16v2.553 (3)N7···C31x3.454 (4)
O3···C34v3.265 (4)N7···C31vii3.387 (4)
O3···C35v3.338 (4)N8···C30x3.525 (4)
O3···C36v3.260 (4)N8···H20x3.22
O3···C51v3.541 (4)N8···H20vii3.51
O4···O9vi2.538 (3)N9···H17x3.31
O4···C20vi3.296 (4)N11···C16v3.584 (4)
O4···C22vi3.571 (4)N11···C16viii3.490 (4)
O4···C38v3.428 (4)N11···C17v3.379 (4)
O5···O6vi2.771 (3)N11···C17viii3.317 (4)
O5···O9vi3.460 (3)N11···C18v3.455 (4)
O6···C43vii3.236 (4)N11···C18viii3.382 (4)
O6···C44vii3.599 (4)N11···C19viii3.591 (4)
O8···O12viii2.712 (3)N12···C17v3.543 (4)
O8···C14v3.327 (4)N15···C1xi3.456 (4)
O8···C14viii3.319 (4)N15···C4v3.316 (5)
O8···C15v3.369 (4)N15···C4viii3.459 (5)
O8···C15viii3.358 (4)N15···C5v3.368 (5)
O9···C9ix3.376 (4)N15···C5viii3.203 (5)
O10···O21vii2.559 (3)N15···C6viii3.514 (4)
O10···C46vii3.507 (4)C1···C1iii3.412 (5)
O10···H7ix3.14C1···C1iv3.412 (5)
O11···O12ix2.708 (3)C1···C2iii3.462 (5)
O12···C30x3.335 (4)C1···C2iv3.429 (5)
O14···O18vii2.704 (3)C4···C52v3.525 (5)
O14···C27x3.359 (4)C4···C52viii3.176 (5)
O14···C27vii3.317 (4)C5···C51v3.212 (5)
O14···C28x3.354 (4)C6···C51v3.581 (5)
O14···C28vii3.338 (4)C11···C44vii3.341 (4)
O15···O22ix2.548 (3)C12···C44vii3.298 (5)
O15···O23ix3.302 (3)C12···C45vii3.544 (5)
O15···C48ix3.313 (4)C13···C43x3.499 (5)
O16···C7viii3.444 (4)C13···C43vii3.116 (5)
O17···O18ix2.697 (3)C13···C44x3.564 (5)
O18···C17v3.344 (4)C13···C44vii3.385 (5)
O19···O20i3.443 (3)C14···C14v3.406 (5)
O19···N3xi3.403 (3)C14···C14viii3.406 (5)
O19···C13xi3.288 (4)C16···C39v3.531 (4)
O19···C41i3.461 (4)C17···C39v3.278 (4)
O19···C42i3.318 (4)C17···C39viii3.335 (4)
O20···O24i2.752 (3)C18···C37viii3.469 (5)
O20···N3xi2.763 (3)C18···C38v3.318 (4)
O20···N13xii3.162 (4)C18···C38viii3.225 (4)
O20···C13xi3.540 (3)C19···C38v3.585 (5)
O20···C40xii3.416 (4)C19···C38viii3.544 (5)
O20···C41xii3.218 (4)C20···H25viii3.50
O20···C41i3.524 (4)C24···C31x3.459 (4)
O21···C21x3.250 (4)C25···C30x3.577 (4)
O21···C22x3.348 (4)C25···C31x3.206 (4)
O21···C23x3.301 (4)C25···C31vii3.340 (4)
O22···C25x3.386 (4)C25···C32x3.583 (4)
O22···C33vi3.395 (4)C26···C29vii3.582 (4)
O23···O242.692 (3)C26···C30x3.325 (4)
O23···C49vi3.411 (4)C26···C30vii3.326 (4)
O24···C4v3.236 (4)C27···C27x3.435 (5)
O24···C40xii3.581 (4)C27···C27vii3.435 (5)
O24···C42xii3.468 (4)C40···C40xii3.318 (5)
N4···C43vii3.330 (4)C40···C40i3.318 (5)
N4···C44vii3.405 (4)C40···C41xii3.393 (4)
N3···C40ii3.429 (4)C40···C41i3.411 (4)
O1—Cu1—O689.71 (9)N3—C13—H9125
O1—Cu1—N179.5 (1)O7—C14—O8125.2 (3)
O6—Cu1—N194.95 (11)O7—C14—C15116.2 (2)
O1—Cu1—N2159.8 (1)O8—C14—C15118.7 (3)
O6—Cu1—N298.45 (9)N5—C15—C14111.8 (2)
N1—Cu1—N281.36 (12)N5—C15—C16119.7 (3)
O1—Cu1—N4101.62 (11)C14—C15—C16128.5 (3)
O6—Cu1—N496.87 (9)C15—C16—C17118.4 (3)
N1—Cu1—N4168.13 (12)C15—C16—H10121
N2—Cu1—N495.74 (12)C17—C16—H10121
O7—Cu2—O1286.75 (8)C16—C17—C18120.4 (3)
O7—Cu2—N579.86 (9)C16—C17—H11120
O12—Cu2—N596.3 (1)C18—C17—H11120
O7—Cu2—N6157.80 (9)C17—C18—C19117.8 (3)
O12—Cu2—N6105.88 (9)C17—C18—H12121
N5—Cu2—N680.6 (1)C19—C18—H12121
O7—Cu2—N8102.45 (9)N5—C19—C18120.4 (3)
O12—Cu2—N891.3 (1)N5—C19—C20112.2 (3)
N5—Cu2—N8172.25 (12)C18—C19—C20127.1 (3)
N6—Cu2—N895.6 (1)O9—C20—N6128.9 (3)
O13—Cu3—O1886.75 (8)O9—C20—C19119.0 (3)
O13—Cu3—N979.48 (9)N6—C20—C19112.1 (3)
O18—Cu3—N996.72 (9)N6—C21—C22109.8 (2)
O13—Cu3—N10157.44 (9)N6—C21—C23109.9 (3)
O18—Cu3—N10106.43 (9)C22—C21—C23110.7 (3)
N9—Cu3—N1080.8 (1)N6—C21—H13109
O13—Cu3—N12102.43 (9)C22—C21—H13109
O18—Cu3—N1291.3 (1)C23—C21—H13109
N9—Cu3—N12171.83 (12)O10—C22—O11120.3 (3)
N10—Cu3—N1295.6 (1)O10—C22—C21116.1 (3)
O19—Cu4—O2488.53 (9)O11—C22—C21123.6 (3)
O19—Cu4—N1379.5 (1)C21—C23—C24115.5 (3)
O24—Cu4—N1397.2 (1)C21—C23—H14108
O19—Cu4—N14160.9 (1)C24—C23—H14108
O24—Cu4—N1495.9 (1)C21—C23—H15108
N13—Cu4—N1481.47 (11)C24—C23—H15108
O19—Cu4—N16102.61 (11)H14—C23—H15110
O24—Cu4—N1693.19 (11)N8—C24—C23122.1 (3)
N13—Cu4—N16169.46 (13)N8—C24—C25108.2 (3)
N14—Cu4—N1695.74 (12)C23—C24—C25129.4 (3)
Cu1—O1—C1114.16 (19)N7—C25—C24106.9 (3)
Cu2—O7—C14113.16 (18)N7—C25—H16127
Cu3—O13—C27113.56 (19)C24—C25—H16127
Cu4—O19—C40114.27 (19)N7—C26—N8110.7 (3)
Cu1—N1—C2119.5 (2)N7—C26—H18125
Cu1—N1—C6117.0 (2)N8—C26—H18125
C2—N1—C6123.5 (3)O13—C27—O14125.7 (3)
Cu1—N2—C7116.0 (2)O13—C27—C28115.7 (3)
Cu1—N2—C8126.1 (2)O14—C27—C28118.6 (3)
C7—N2—C8117.8 (3)N9—C28—C27111.4 (2)
Cu1—N4—C11122.6 (2)N9—C28—C29120.3 (3)
Cu1—N4—C13130.3 (2)C27—C28—C29128.2 (3)
C11—N4—C13107.1 (3)C28—C29—C30118.0 (3)
C12—N3—C13107.8 (3)C28—C29—H19121
C12—N3—H8126C30—C29—H19121
C13—N3—H8126C29—C30—C31120.4 (3)
Cu2—N5—C15118.9 (2)C29—C30—H20120
Cu2—N5—C19117.8 (2)C31—C30—H20120
C15—N5—C19123.3 (3)C30—C31—C32117.9 (3)
Cu2—N6—C20116.6 (2)C30—C31—H21121
Cu2—N6—C21124.7 (2)C32—C31—H21121
C20—N6—C21118.6 (3)N9—C32—C31120.2 (3)
C25—N7—C26107.5 (3)N9—C32—C33112.2 (3)
C25—N7—H17126C31—C32—C33127.3 (3)
C26—N7—H17126O15—C33—N10128.5 (3)
Cu2—N8—C24124.2 (2)O15—C33—C32119.3 (3)
Cu2—N8—C26129.1 (2)N10—C33—C32112.1 (3)
C24—N8—C26106.7 (2)N10—C34—C35110.1 (3)
Cu3—N9—C28119.4 (2)N10—C34—C36109.8 (3)
Cu3—N9—C32117.5 (2)C35—C34—C36111.0 (3)
C28—N9—C32123.0 (3)N10—C34—H22109
Cu3—N10—C33116.6 (2)C35—C34—H22109
Cu3—N10—C34124.1 (2)C36—C34—H22109
C33—N10—C34118.3 (3)O16—C35—O17120.0 (3)
C38—N11—C39107.6 (2)O16—C35—C34117.2 (3)
C38—N11—H26126O17—C35—C34122.7 (3)
C39—N11—H26126C34—C36—C37115.1 (3)
Cu3—N12—C37124.3 (2)C34—C36—H23108
Cu3—N12—C39128.9 (2)C37—C36—H23108
C37—N12—C39106.8 (2)C34—C36—H24108
Cu4—N13—C41119.6 (2)C37—C36—H24108
Cu4—N13—C45117.2 (2)H23—C36—H24110
C41—N13—C45123.1 (3)N12—C37—C36122.2 (2)
Cu4—N14—C46115.0 (2)N12—C37—C38108.3 (3)
Cu4—N14—C47125.6 (2)C36—C37—C38129.3 (3)
C46—N14—C47118.2 (3)N11—C38—C37106.7 (3)
C51—N15—C52108.4 (3)N11—C38—H25127
C51—N15—H35126C37—C38—H25127
C52—N15—H35126N11—C39—N12110.7 (3)
Cu4—N16—C50123.9 (2)N11—C39—H27125
Cu4—N16—C52127.4 (2)N12—C39—H27125
C50—N16—C52106.7 (3)O19—C40—O20126.4 (3)
O1—C1—O2126.4 (3)O19—C40—C41114.9 (3)
O1—C1—C2115.0 (3)O20—C40—C41118.7 (3)
O2—C1—C2118.5 (2)N13—C41—C40111.7 (3)
N1—C2—C1111.5 (2)N13—C41—C42120.8 (3)
N1—C2—C3120.8 (3)C40—C41—C42127.5 (3)
C1—C2—C3127.7 (3)C41—C42—C43117.4 (3)
C2—C3—C4117.3 (3)C41—C42—H28121
C2—C3—H1121C43—C42—H28121
C4—C3—H1121C42—C43—C44120.8 (3)
C3—C4—C5120.6 (3)C42—C43—H29120
C3—C4—H2120C44—C43—H29120
C5—C4—H2120C43—C44—C45117.8 (3)
C4—C5—C6118.3 (3)C43—C44—H30121
C4—C5—H3121C45—C44—H30121
C6—C5—H3121N13—C45—C44120.0 (3)
N1—C6—C5119.5 (3)N13—C45—C46112.9 (3)
N1—C6—C7112.8 (3)C44—C45—C46127.1 (3)
C5—C6—C7127.7 (3)O21—C46—N14128.3 (3)
O3—C7—N2128.3 (3)O21—C46—C45118.9 (3)
O3—C7—C6119.2 (3)N14—C46—C45112.9 (3)
N2—C7—C6112.4 (3)N14—C47—C48111.4 (3)
N2—C8—C9112.0 (3)N14—C47—C49111.5 (3)
N2—C8—C10111.0 (3)C48—C47—C49111.5 (3)
C9—C8—C10110.2 (3)N14—C47—H31107
N2—C8—H4108C48—C47—H31107
C9—C8—H4108C49—C47—H31108
C10—C8—H4108O22—C48—O23122.8 (3)
O4—C9—O5124.5 (3)O22—C48—C47113.1 (3)
O4—C9—C8111.2 (3)O23—C48—C47124.1 (3)
O5—C9—C8124.3 (3)C47—C49—C50117.3 (3)
C8—C10—C11115.5 (3)C47—C49—H32107
C8—C10—H5108C50—C49—H32107
C11—C10—H5108C47—C49—H33108
C8—C10—H6108C50—C49—H33108
C11—C10—H6108H32—C49—H33110
H5—C10—H6109N16—C50—C49122.9 (3)
N4—C11—C10122.6 (3)N16—C50—C51108.1 (3)
N4—C11—C12108.3 (3)C49—C50—C51128.1 (3)
C10—C11—C12128.8 (3)N15—C51—C50106.8 (3)
N3—C12—C11106.3 (3)N15—C51—H34127
N3—C12—H7127C50—C51—H34127
C11—C12—H7127N15—C52—N16110.0 (3)
N4—C13—N3110.5 (3)N15—C52—H36125
N4—C13—H9125N16—C52—H36125
O6—Cu1—O1—C192.5 (4)C25—N7—C26—N80.3 (5)
N1—Cu1—O1—C12.6 (4)Cu2—N8—C24—C234.1 (5)
N2—Cu1—O1—C121.9 (5)Cu2—N8—C24—C25178.5 (2)
N4—Cu1—O1—C1170.6 (4)C26—N8—C24—C23173.4 (4)
O1—Cu1—N1—C24.9 (4)C26—N8—C24—C251.1 (5)
O1—Cu1—N1—C6177.2 (4)Cu2—N8—C26—N7177.8 (2)
O6—Cu1—N1—C283.9 (5)C24—N8—C26—N70.5 (5)
O6—Cu1—N1—C694.0 (4)Cu3—N9—C28—C274.9 (4)
N2—Cu1—N1—C2178.3 (5)Cu3—N9—C28—C29177.0 (3)
N2—Cu1—N1—C63.8 (5)C32—N9—C28—C27177.1 (4)
N4—Cu1—N1—C2101.7 (6)C32—N9—C28—C291.0 (6)
N4—Cu1—N1—C680.3 (7)Cu3—N9—C32—C31175.8 (3)
O1—Cu1—N2—C719.0 (4)Cu3—N9—C32—C339.4 (4)
O1—Cu1—N2—C8156.0 (3)C28—N9—C32—C312.2 (6)
O6—Cu1—N2—C794.0 (4)C28—N9—C32—C33172.6 (4)
O6—Cu1—N2—C891.1 (2)Cu3—N10—C33—O15176.0 (3)
N1—Cu1—N2—C70.2 (2)Cu3—N10—C33—C320.8 (4)
N1—Cu1—N2—C8175.1 (5)C34—N10—C33—O157.0 (7)
N4—Cu1—N2—C7168.2 (4)C34—N10—C33—C32169.9 (4)
N4—Cu1—N2—C86.7 (6)Cu3—N10—C34—C3579.4 (4)
O1—Cu1—N4—C11171.1 (4)Cu3—N10—C34—C3643.1 (4)
O1—Cu1—N4—C138.1 (6)C33—N10—C34—C3588.8 (5)
O6—Cu1—N4—C1180.0 (2)C33—N10—C34—C36148.8 (4)
O6—Cu1—N4—C1399.2 (5)C39—N11—C38—C370.9 (5)
N1—Cu1—N4—C1194.3 (6)C38—N11—C39—N120.1 (5)
N1—Cu1—N4—C1386.5 (7)Cu3—N12—C37—C363.6 (4)
N2—Cu1—N4—C1119.3 (2)Cu3—N12—C37—C38179.0 (2)
N2—Cu1—N4—C13161.5 (5)C39—N12—C37—C36173.9 (4)
O12—Cu2—O7—C1492.8 (4)C39—N12—C37—C381.4 (5)
N5—Cu2—O7—C144.1 (4)Cu3—N12—C39—N11178.2 (2)
N6—Cu2—O7—C1433.0 (4)C37—N12—C39—N110.8 (5)
N8—Cu2—O7—C14176.6 (4)Cu4—N13—C41—C403.1 (4)
O7—Cu2—N5—C153.8 (4)Cu4—N13—C41—C42177.6 (3)
O7—Cu2—N5—C19177.2 (4)C45—N13—C41—C40179.2 (4)
O12—Cu2—N5—C1581.8 (4)C45—N13—C41—C421.5 (7)
O12—Cu2—N5—C1997.2 (4)Cu4—N13—C45—C44176.1 (3)
N6—Cu2—N5—C15173.1 (4)Cu4—N13—C45—C464.3 (4)
N6—Cu2—N5—C197.9 (4)C41—N13—C45—C440.1 (7)
O7—Cu2—N6—C2035.6 (4)C41—N13—C45—C46179.5 (4)
O7—Cu2—N6—C21139.8 (6)Cu4—N14—C46—O21171.1 (3)
O12—Cu2—N6—C2087.1 (4)Cu4—N14—C46—C458.2 (4)
O12—Cu2—N6—C2197.4 (4)C47—N14—C46—O213.3 (7)
N5—Cu2—N6—C206.8 (4)C47—N14—C46—C45176.0 (4)
N5—Cu2—N6—C21168.7 (4)Cu4—N14—C47—C4884.1 (4)
N8—Cu2—N6—C20180.0 (4)Cu4—N14—C47—C4941.1 (4)
N8—Cu2—N6—C214.5 (5)C46—N14—C47—C4882.2 (5)
O7—Cu2—N8—C24177.9 (4)C46—N14—C47—C49152.5 (4)
O7—Cu2—N8—C261.1 (5)C52—N15—C51—C500.7 (5)
O12—Cu2—N8—C2491.0 (4)C51—N15—C52—N160.6 (6)
O12—Cu2—N8—C2685.9 (5)Cu4—N16—C50—C4925.4 (5)
N6—Cu2—N8—C2415.1 (5)Cu4—N16—C50—C51164.2 (2)
N6—Cu2—N8—C26168.0 (4)C52—N16—C50—C49170.1 (4)
O18—Cu3—O13—C2791.9 (4)C52—N16—C50—C510.3 (5)
N9—Cu3—O13—C275.6 (4)Cu4—N16—C52—N15164.0 (2)
N10—Cu3—O13—C2735.2 (4)C50—N16—C52—N150.2 (5)
N12—Cu3—O13—C27177.5 (4)O1—C1—C2—N13.4 (5)
O13—Cu3—N9—C285.7 (4)O1—C1—C2—C3178.6 (4)
O13—Cu3—N9—C32176.2 (4)O2—C1—C2—N1176.5 (4)
O18—Cu3—N9—C2879.7 (4)O2—C1—C2—C31.5 (7)
O18—Cu3—N9—C3298.4 (4)N1—C2—C3—C40.3 (6)
N10—Cu3—N9—C28174.7 (4)C1—C2—C3—C4178.1 (4)
N10—Cu3—N9—C327.2 (4)C2—C3—C4—C51.8 (7)
O13—Cu3—N10—C3332.7 (4)C3—C4—C5—C61.4 (7)
O13—Cu3—N10—C34135.7 (6)C4—C5—C6—N10.6 (7)
O18—Cu3—N10—C3391.2 (4)C4—C5—C6—C7176.8 (4)
O18—Cu3—N10—C34100.5 (4)N1—C6—C7—O3171.6 (4)
N9—Cu3—N10—C333.2 (4)N1—C6—C7—N26.6 (6)
N9—Cu3—N10—C34165.2 (4)C5—C6—C7—O35.9 (8)
N12—Cu3—N10—C33175.8 (4)C5—C6—C7—N2175.9 (5)
N12—Cu3—N10—C347.4 (5)N2—C8—C9—O4160.2 (4)
O13—Cu3—N12—C37179.4 (4)N2—C8—C9—O521.2 (6)
O13—Cu3—N12—C392.5 (5)C10—C8—C9—O475.7 (5)
O18—Cu3—N12—C3792.5 (4)C10—C8—C9—O5103.0 (5)
O18—Cu3—N12—C3984.5 (5)N2—C8—C10—C1159.0 (5)
N10—Cu3—N12—C39168.9 (4)C9—C8—C10—C1165.8 (5)
O24—Cu4—O19—C4096.9 (4)C8—C10—C11—N450.3 (6)
N13—Cu4—O19—C400.7 (4)C8—C10—C11—C12137.4 (5)
N14—Cu4—O19—C406.8 (5)N4—C11—C12—N30.5 (5)
N16—Cu4—O19—C40170.1 (4)C10—C11—C12—N3172.7 (4)
O19—Cu4—N13—C411.6 (4)O7—C14—C15—N50.9 (5)
O19—Cu4—N13—C45177.9 (4)O7—C14—C15—C16177.3 (4)
O24—Cu4—N13—C4188.7 (4)O8—C14—C15—N5179.9 (3)
O24—Cu4—N13—C4594.9 (4)O8—C14—C15—C161.9 (6)
N14—Cu4—N13—C41176.4 (4)N5—C15—C16—C170.6 (6)
N14—Cu4—N13—C450.0 (5)C14—C15—C16—C17178.6 (4)
N16—Cu4—N13—C41100.8 (7)C15—C16—C17—C180.6 (6)
N16—Cu4—N13—C4575.5 (7)C16—C17—C18—C190.1 (6)
O19—Cu4—N14—C4611.1 (5)C17—C18—C19—N50.8 (6)
O19—Cu4—N14—C47177.8 (3)C17—C18—C19—C20172.7 (4)
O24—Cu4—N14—C4691.6 (4)N5—C19—C20—O9175.5 (4)
O24—Cu4—N14—C4775.2 (2)N5—C19—C20—N61.7 (5)
N13—Cu4—N14—C464.9 (2)C18—C19—C20—O91.6 (7)
N13—Cu4—N14—C47171.6 (5)C18—C19—C20—N6175.6 (4)
N16—Cu4—N14—C46174.6 (4)N6—C21—C22—O10172.6 (4)
N16—Cu4—N14—C4718.6 (6)N6—C21—C22—O1110.5 (6)
O19—Cu4—N16—C50176.9 (4)C23—C21—C22—O1065.9 (6)
O19—Cu4—N16—C5215.7 (6)C23—C21—C22—O11111.0 (5)
O24—Cu4—N16—C5087.7 (5)N6—C21—C23—C2463.1 (5)
O24—Cu4—N16—C5273.5 (5)C22—C21—C23—C2458.4 (6)
N13—Cu4—N16—C5082.8 (7)C21—C23—C24—N847.2 (6)
N13—Cu4—N16—C52116.0 (6)C21—C23—C24—C25139.6 (5)
N14—Cu4—N16—C508.5 (6)N8—C24—C25—N71.2 (4)
N14—Cu4—N16—C52169.7 (5)C23—C24—C25—N7172.7 (4)
Cu1—O1—C1—O2179.8 (3)O13—C27—C28—N90.2 (5)
Cu1—O1—C1—C20.3 (4)O13—C27—C28—C29177.7 (4)
Cu2—O7—C14—O8177.1 (3)O14—C27—C28—N9179.3 (3)
Cu2—O7—C14—C153.8 (4)O14—C27—C28—C291.3 (6)
Cu3—O13—C27—O14176.4 (3)N9—C28—C29—C300.6 (6)
Cu3—O13—C27—C284.6 (4)C27—C28—C29—C30178.4 (4)
Cu4—O19—C40—O20176.8 (3)C28—C29—C30—C311.0 (6)
Cu4—O19—C40—C412.4 (4)C29—C30—C31—C320.1 (6)
Cu1—N1—C2—C15.9 (4)C30—C31—C32—N91.7 (6)
Cu1—N1—C2—C3176.0 (3)C30—C31—C32—C33172.2 (4)
C6—N1—C2—C1176.4 (4)N9—C32—C33—O15170.8 (4)
C6—N1—C2—C31.8 (7)N9—C32—C33—N106.4 (5)
Cu1—N1—C6—C5175.6 (3)C31—C32—C33—O153.6 (7)
Cu1—N1—C6—C76.7 (4)C31—C32—C33—N10179.2 (4)
C2—N1—C6—C52.2 (7)N10—C34—C35—O16174.9 (4)
C2—N1—C6—C7175.5 (4)N10—C34—C35—O177.4 (6)
Cu1—N2—C7—O3174.3 (3)C36—C34—C35—O1663.3 (5)
Cu1—N2—C7—C63.7 (4)C36—C34—C35—O17114.4 (5)
C8—N2—C7—O31.0 (7)N10—C34—C36—C3764.3 (5)
C8—N2—C7—C6179.0 (4)C35—C34—C36—C3757.6 (5)
Cu1—N2—C8—C995.6 (3)C34—C36—C37—N1246.2 (6)
Cu1—N2—C8—C1028.1 (4)C34—C36—C37—C38139.5 (5)
C7—N2—C8—C979.2 (5)N12—C37—C38—N111.5 (4)
C7—N2—C8—C10157.1 (4)C36—C37—C38—N11173.5 (4)
Cu1—N4—C11—C105.8 (5)O19—C40—C41—N133.6 (5)
Cu1—N4—C11—C12179.5 (2)O19—C40—C41—C42177.2 (4)
C13—N4—C11—C10173.6 (4)O20—C40—C41—N13175.7 (3)
C13—N4—C11—C120.1 (5)O20—C40—C41—C423.5 (6)
Cu1—N4—C13—N3179.0 (2)N13—C41—C42—C432.1 (6)
C11—N4—C13—N30.4 (5)C40—C41—C42—C43178.7 (4)
C13—N3—C12—C110.7 (5)C41—C42—C43—C441.3 (6)
C12—N3—C13—N40.6 (5)C42—C43—C44—C450.3 (7)
Cu2—N5—C15—C142.8 (4)C43—C44—C45—N131.0 (7)
Cu2—N5—C15—C16178.8 (3)C43—C44—C45—C46178.6 (4)
C19—N5—C15—C14178.2 (4)N13—C45—C46—O21171.2 (4)
C19—N5—C15—C160.1 (6)N13—C45—C46—N148.2 (6)
Cu2—N5—C19—C18178.1 (3)C44—C45—C46—O218.4 (8)
Cu2—N5—C19—C207.5 (4)C44—C45—C46—N14172.2 (5)
C15—N5—C19—C180.8 (6)N14—C47—C48—O22159.5 (4)
C15—N5—C19—C20173.6 (4)N14—C47—C48—O2321.5 (6)
Cu2—N6—C20—O9178.6 (3)C49—C47—C48—O2275.3 (5)
Cu2—N6—C20—C194.6 (4)C49—C47—C48—O23103.7 (5)
C21—N6—C20—O95.7 (7)N14—C47—C49—C5054.5 (5)
C21—N6—C20—C19171.1 (4)C48—C47—C49—C5070.6 (5)
Cu2—N6—C21—C2282.2 (4)C47—C49—C50—N1649.5 (7)
Cu2—N6—C21—C2339.8 (4)C47—C49—C50—C51142.1 (5)
C20—N6—C21—C2293.2 (5)N16—C50—C51—N150.6 (5)
C20—N6—C21—C23144.8 (4)C49—C50—C51—N15169.1 (4)
C26—N7—C25—C240.9 (5)
Symmetry codes: (i) x, y+1/2, z+2; (ii) x, y, z1; (iii) x+1, y1/2, z; (iv) x+1, y+1/2, z; (v) x+1, y1/2, z+1; (vi) x, y1, z; (vii) x, y+1/2, z+1; (viii) x+1, y+1/2, z+1; (ix) x, y+1, z; (x) x, y1/2, z+1; (xi) x, y, z+1; (xii) x, y1/2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H8···O20ii0.951.862.763 (3)159
N7—H17···O140.951.832.730 (3)158
N11—H26···O80.951.822.732 (3)159
N15—H35···O2xi0.951.872.788 (4)161
Symmetry codes: (ii) x, y, z1; (xi) x, y, z+1.

Experimental details

Crystal data
Chemical formula[CuH2O(C13H10N4O5)]
Mr383.81
Crystal system, space groupMonoclinic, P21
Temperature (K)123
a, b, c (Å)15.983 (1), 6.5095 (4), 29.068 (1)
β (°) 102.2801 (5)
V3)2955.0 (3)
Z8
Radiation typeMo Kα
µ (mm1)1.52
Crystal size (mm)0.2 × 0.2 × 0.1
Data collection
DiffractometerRigaku Mercury CCD area-detector
diffractometer
Absorption correctionMulti-scan
(Blessing, 1995)
Tmin, Tmax0.731, 0.859
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
21831, 12299, 11052
Rint0.076
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.074, 1.34
No. of reflections12299
No. of parameters902
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.90, 1.03
Absolute structure5197 Friedel pairs (Flack, 1983)
Absolute structure parameter0.015 (7)

Computer programs: CrystalClear (Rigaku, 2001), CrystalClear, CrystalStructure (Rigaku, 2001), SIR97 (Altomare, 1998), CRYSTALS (Watkin et al., 1996), ORTEP-3 (Farrugia, 1997), CrystalStructure.

Selected geometric parameters (Å, º) top
Cu1—O12.065 (2)Cu3—O132.076 (2)
Cu1—O62.347 (2)Cu3—O182.275 (3)
Cu1—N11.917 (3)Cu3—N91.920 (2)
Cu1—N21.976 (3)Cu3—N101.974 (3)
Cu1—N41.928 (3)Cu3—N121.930 (2)
Cu2—O72.073 (2)Cu4—O192.067 (2)
Cu2—O122.296 (2)Cu4—O242.333 (2)
Cu2—N51.920 (2)Cu4—N131.917 (3)
Cu2—N61.975 (3)Cu4—N141.993 (3)
Cu2—N81.926 (2)Cu4—N161.922 (3)
O3···O16i2.553 (3)O23···O242.692 (3)
O4···O9ii2.538 (3)
O1—Cu1—O689.71 (9)O13—Cu3—O1886.75 (8)
O1—Cu1—N179.5 (1)O13—Cu3—N979.48 (9)
O6—Cu1—N194.95 (11)O18—Cu3—N996.72 (9)
O1—Cu1—N2159.8 (1)O13—Cu3—N10157.44 (9)
O6—Cu1—N298.45 (9)O18—Cu3—N10106.43 (9)
N1—Cu1—N281.36 (12)N9—Cu3—N1080.8 (1)
O1—Cu1—N4101.62 (11)O13—Cu3—N12102.43 (9)
O6—Cu1—N496.87 (9)O18—Cu3—N1291.3 (1)
N1—Cu1—N4168.13 (12)N9—Cu3—N12171.83 (12)
N2—Cu1—N495.74 (12)N10—Cu3—N1295.6 (1)
O7—Cu2—O1286.75 (8)O19—Cu4—O2488.53 (9)
O7—Cu2—N579.86 (9)O19—Cu4—N1379.5 (1)
O12—Cu2—N596.3 (1)O24—Cu4—N1397.2 (1)
O7—Cu2—N6157.80 (9)O19—Cu4—N14160.9 (1)
O12—Cu2—N6105.88 (9)O24—Cu4—N1495.9 (1)
N5—Cu2—N680.6 (1)N13—Cu4—N1481.47 (11)
O7—Cu2—N8102.45 (9)O19—Cu4—N16102.61 (11)
O12—Cu2—N891.3 (1)O24—Cu4—N1693.19 (11)
N5—Cu2—N8172.25 (12)N13—Cu4—N16169.46 (13)
N6—Cu2—N895.6 (1)N14—Cu4—N1695.74 (12)
Symmetry codes: (i) x+1, y1/2, z+1; (ii) x, y1, z.
 

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