Triaqua-bis(1H-imidazole)bis-[μ(2)-2-(oxalo-amino)benzoato(3-)]dicopper(II)calcium(II) hepta-hydrate.

In the title heterotrinuclear coordination compound, [CaCu(2)(C(9)H(4)NO(5))(2)(C(3)H(4)N(2))(2)(H(2)O)(3)]·7H(2)O, the Ca(2+) cation is in a penta-gonal-bipyramidal geometry and bridges two (1H-imidazole)[2-(oxaloamino)benzoato(3-)]copper(II) units in its equatorial plane. Each Cu(II) atom has a normal square-planar geometry. The mol-ecule has approximate local (non-crystallographic) mirror symmetry and 23 classical hydrogen bonds are found in the crystal structure.

Related literature

For related literature, see: Zang et al. (2003 ▶).

Experimental

Crystal data

[CaCu2(C9H4NO5)2(C3H4N2)2(H2O)3]·7H2O

M = 895.75

Monoclinic,

a = 6.8988 (9) Å

b = 24.011 (3) Å

c = 21.161 (3) Å

β = 93.511 (3)°

V = 3498.7 (8) Å3

Z = 4

Mo Kα radiation

μ = 1.45 mm−1

T = 293 (2) K

0.2 × 0.2 × 0.2 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.75, T max = 0.76

17203 measured reflections

6119 independent reflections

3486 reflections with I > 2σ(I)

R int = 0.093

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.122

S = 0.99

6119 reflections

478 parameters

7 restraints

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.48 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807067517/si2057sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067517/si2057Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[CaCu2(C9H4NO5)2(C3H4N2)2(H2O)3]·7H2O	F000 = 1840
Mr = 895.75	Dx = 1.701 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1959 reflections
a = 6.8988 (9) Å	θ = 2.7–20.5º
b = 24.011 (3) Å	µ = 1.45 mm−1
c = 21.161 (3) Å	T = 293 (2) K
β = 93.511 (3)º	Block, green
V = 3498.7 (8) Å3	0.2 × 0.2 × 0.2 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	6119 independent reflections
Radiation source: fine-focus sealed tube	3486 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.093
T = 293(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.75, Tmax = 0.76	k = −28→28
17203 measured reflections	l = −15→25

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063	H-atom parameters constrained
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.03P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.018
6119 reflections	Δρmax = 0.59 e Å−3
478 parameters	Δρmin = −0.48 e Å−3
7 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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 of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Ca1	0.57052 (19)	0.21723 (5)	0.36790 (5)	0.0305 (3)
Cu1	0.42034 (12)	0.15913 (3)	0.10945 (3)	0.0365 (2)
Cu2	0.40057 (12)	0.12870 (3)	0.60805 (3)	0.0303 (2)
N1	0.4528 (7)	0.20197 (17)	0.57516 (19)	0.0223 (12)
N2	0.4559 (7)	0.22668 (18)	0.1570 (2)	0.0275 (12)
C1	0.4976 (10)	0.2460 (3)	0.0207 (3)	0.0400 (17)
C2	0.4626 (8)	0.2899 (2)	0.0672 (3)	0.0273 (15)
C3	0.4444 (9)	0.3438 (3)	0.0446 (3)	0.0405 (17)
H3	0.4611	0.3502	0.0019	0.049*
C4	0.4034 (10)	0.3877 (3)	0.0816 (3)	0.0460 (19)
H4	0.3903	0.4232	0.0645	0.055*
C5	0.3812 (10)	0.3788 (3)	0.1455 (3)	0.0422 (18)
H5	0.3532	0.4085	0.1716	0.051*
C6	0.4004 (9)	0.3262 (2)	0.1701 (3)	0.0326 (16)
H6	0.3856	0.3206	0.2131	0.039*
C7	0.4416 (8)	0.2810 (2)	0.1321 (2)	0.0260 (14)
C8	0.4955 (9)	0.2169 (2)	0.2188 (3)	0.0278 (15)
C9	0.4692 (9)	0.1558 (2)	0.2362 (3)	0.0294 (15)
N3	0.3548 (9)	0.0899 (2)	0.0656 (3)	0.0497 (16)
C10	0.3866 (13)	0.0390 (3)	0.0854 (4)	0.070 (3)
H10	0.4524	0.0299	0.1236	0.084*
N4	0.3135 (12)	0.0024 (3)	0.0442 (4)	0.091 (3)
H4A	0.3211	−0.0332	0.0478	0.109*
C11	0.2251 (14)	0.0305 (4)	−0.0043 (4)	0.083 (3)
H11	0.1579	0.0154	−0.0397	0.099*
C12	0.2529 (12)	0.0841 (4)	0.0084 (4)	0.070 (2)
H12	0.2098	0.1133	−0.0177	0.084*
C13	0.4628 (9)	0.1977 (3)	0.7176 (3)	0.0309 (16)
C14	0.4633 (8)	0.2491 (2)	0.6780 (3)	0.0268 (15)
C15	0.4633 (9)	0.2996 (3)	0.7113 (3)	0.0417 (18)
H15	0.4738	0.2986	0.7553	0.050*
C16	0.4481 (10)	0.3508 (3)	0.6814 (3)	0.0451 (19)
H16	0.4443	0.3836	0.7046	0.054*
C17	0.4390 (10)	0.3517 (2)	0.6165 (3)	0.0422 (18)
H17	0.4291	0.3857	0.5954	0.051*
C18	0.4441 (9)	0.3035 (2)	0.5821 (3)	0.0352 (17)
H18	0.4390	0.3057	0.5382	0.042*
C19	0.4568 (8)	0.2516 (2)	0.6106 (3)	0.0258 (15)
C20	0.4908 (8)	0.2006 (2)	0.5142 (3)	0.0247 (14)
C21	0.4483 (9)	0.1434 (2)	0.4842 (3)	0.0305 (16)
N5	0.3638 (8)	0.05199 (19)	0.6339 (2)	0.0339 (14)
C22	0.2829 (10)	0.0326 (3)	0.6870 (3)	0.0466 (19)
H22	0.2244	0.0544	0.7169	0.056*
C23	0.3020 (12)	−0.0230 (3)	0.6888 (4)	0.061 (2)
H23	0.2597	−0.0466	0.7199	0.074*
N6	0.3947 (9)	−0.0383 (2)	0.6367 (3)	0.0591 (18)
H6A	0.4251	−0.0716	0.6261	0.071*
C24	0.4289 (10)	0.0077 (3)	0.6058 (3)	0.0468 (19)
H24	0.4919	0.0088	0.5682	0.056*
O1	0.5537 (7)	0.26049 (18)	−0.03227 (19)	0.0528 (13)
O2	0.4690 (7)	0.19479 (18)	0.03125 (17)	0.0415 (12)
O3	0.4352 (7)	0.12114 (15)	0.19170 (18)	0.0423 (12)
O4	0.4854 (7)	0.14343 (15)	0.29325 (19)	0.0436 (13)
O5	0.5407 (6)	0.24986 (15)	0.26216 (17)	0.0347 (11)
O6	0.5085 (6)	0.20180 (16)	0.77547 (17)	0.0420 (12)
O7	0.4140 (7)	0.15086 (16)	0.69376 (17)	0.0418 (12)
O8	0.5517 (6)	0.23713 (15)	0.47962 (17)	0.0315 (10)
O9	0.4621 (7)	0.13889 (15)	0.42624 (17)	0.0401 (12)
O10	0.4020 (6)	0.10426 (15)	0.51994 (17)	0.0372 (12)
O11	0.8768 (6)	0.17246 (16)	0.37391 (18)	0.0466 (12)
H11A	0.9524	0.1891	0.4009	0.070*
H11C	0.8666	0.1385	0.3846	0.070*
O12	0.2690 (6)	0.26068 (18)	0.36776 (18)	0.0590 (14)
H12A	0.1876	0.2723	0.3390	0.089*
H12B	0.2011	0.2541	0.3991	0.089*
O13	0.7663 (6)	0.29991 (15)	0.37573 (18)	0.0492 (13)
H13A	0.8576	0.2976	0.3507	0.074*
H13B	0.6965	0.3282	0.3663	0.074*
O14	0.2004 (10)	0.0229 (2)	0.2365 (3)	0.117 (2)
H14C	0.2560	0.0500	0.2192	0.175*
H14D	0.1710	0.0263	0.2747	0.175*
O15	0.1196 (7)	0.08557 (18)	0.3431 (2)	0.0766 (17)
H15A	0.2257	0.1036	0.3467	0.115*
H15D	0.1356	0.0662	0.3767	0.115*
O16	0.1226 (8)	0.02987 (18)	0.4619 (2)	0.0818 (18)
H16A	0.1659	0.0551	0.4871	0.123*
H16B	0.2171	0.0074	0.4592	0.123*
O17	0.1399 (16)	0.0127 (4)	0.8469 (4)	0.252 (5)
H17C	0.0609	−0.0057	0.8226	0.378*
H17D	0.2441	0.0153	0.8276	0.378*
O18	0.6065 (16)	0.0784 (2)	0.7980 (4)	0.265 (7)
H18C	0.6615	0.0481	0.7884	0.397*
H18D	0.5511	0.0987	0.7693	0.397*
O19	0.9605 (13)	0.1133 (3)	0.8665 (4)	0.198 (4)
H19C	1.0155	0.0822	0.8607	0.296*
H19D	0.9021	0.1202	0.8308	0.296*
O20	0.6630 (11)	0.1175 (2)	0.9470 (3)	0.149 (3)
H20C	0.7636	0.1334	0.9343	0.224*
H20D	0.5978	0.1372	0.9715	0.224*

	U11	U22	U33	U12	U13	U23
Ca1	0.0384 (9)	0.0344 (7)	0.0194 (7)	−0.0010 (7)	0.0075 (6)	0.0025 (6)
Cu1	0.0455 (6)	0.0401 (5)	0.0245 (4)	−0.0008 (4)	0.0074 (4)	−0.0051 (4)
Cu2	0.0427 (5)	0.0282 (4)	0.0208 (4)	−0.0017 (4)	0.0095 (4)	0.0012 (4)
N1	0.028 (3)	0.025 (3)	0.015 (3)	−0.007 (2)	0.004 (2)	−0.004 (2)
N2	0.035 (3)	0.028 (3)	0.020 (3)	0.000 (3)	0.007 (2)	0.004 (2)
C1	0.035 (5)	0.059 (5)	0.026 (4)	0.007 (4)	0.003 (3)	0.012 (4)
C2	0.021 (4)	0.039 (4)	0.022 (3)	−0.002 (3)	0.003 (3)	0.011 (3)
C3	0.038 (5)	0.055 (5)	0.030 (4)	−0.006 (4)	0.009 (3)	0.007 (4)
C4	0.050 (5)	0.033 (4)	0.055 (5)	−0.015 (4)	0.001 (4)	0.020 (4)
C5	0.053 (5)	0.029 (4)	0.046 (4)	−0.013 (4)	0.009 (4)	0.001 (3)
C6	0.033 (4)	0.036 (4)	0.029 (4)	−0.004 (3)	0.006 (3)	0.007 (3)
C7	0.025 (4)	0.037 (4)	0.016 (3)	−0.008 (3)	0.005 (3)	0.006 (3)
C8	0.026 (4)	0.037 (4)	0.022 (4)	0.006 (3)	0.008 (3)	0.003 (3)
C9	0.030 (4)	0.029 (4)	0.031 (4)	0.003 (3)	0.009 (3)	0.004 (3)
N3	0.074 (5)	0.041 (4)	0.035 (3)	−0.012 (4)	0.010 (3)	−0.009 (3)
C10	0.101 (8)	0.063 (6)	0.049 (5)	−0.011 (6)	0.022 (5)	−0.025 (5)
N4	0.126 (8)	0.059 (5)	0.092 (6)	−0.026 (5)	0.052 (6)	−0.033 (5)
C11	0.088 (8)	0.096 (8)	0.065 (6)	−0.028 (6)	0.015 (6)	−0.036 (6)
C12	0.067 (6)	0.086 (6)	0.057 (5)	−0.005 (5)	0.001 (4)	−0.022 (5)
C13	0.015 (4)	0.054 (5)	0.024 (4)	0.001 (3)	0.003 (3)	−0.005 (3)
C14	0.025 (4)	0.031 (4)	0.026 (3)	0.005 (3)	0.009 (3)	−0.003 (3)
C15	0.039 (5)	0.053 (5)	0.034 (4)	−0.002 (4)	0.013 (3)	−0.018 (4)
C16	0.048 (5)	0.028 (4)	0.061 (5)	−0.006 (4)	0.018 (4)	−0.026 (4)
C17	0.052 (5)	0.021 (3)	0.056 (5)	−0.005 (3)	0.023 (4)	0.006 (3)
C18	0.049 (5)	0.030 (4)	0.029 (4)	−0.005 (3)	0.022 (3)	−0.004 (3)
C19	0.019 (4)	0.030 (3)	0.029 (3)	−0.002 (3)	0.008 (3)	−0.001 (3)
C20	0.020 (4)	0.028 (4)	0.027 (4)	0.002 (3)	0.005 (3)	−0.002 (3)
C21	0.032 (4)	0.027 (4)	0.033 (4)	−0.001 (3)	0.003 (3)	−0.002 (3)
N5	0.047 (4)	0.026 (3)	0.029 (3)	0.002 (3)	0.010 (3)	0.005 (2)
C22	0.063 (6)	0.034 (4)	0.044 (5)	0.000 (4)	0.023 (4)	0.003 (4)
C23	0.069 (6)	0.060 (6)	0.057 (5)	−0.012 (5)	0.015 (5)	0.025 (4)
N6	0.075 (5)	0.030 (3)	0.072 (5)	0.002 (3)	0.000 (4)	0.009 (3)
C24	0.070 (6)	0.030 (4)	0.042 (4)	0.006 (4)	0.012 (4)	0.006 (4)
O1	0.059 (3)	0.071 (3)	0.031 (2)	0.014 (2)	0.025 (2)	0.010 (2)
O2	0.056 (3)	0.049 (3)	0.020 (2)	0.004 (3)	0.014 (2)	−0.003 (2)
O3	0.073 (4)	0.029 (2)	0.026 (2)	−0.004 (2)	0.008 (2)	−0.003 (2)
O4	0.075 (4)	0.031 (3)	0.026 (2)	−0.006 (2)	0.004 (2)	0.009 (2)
O5	0.054 (3)	0.033 (2)	0.017 (2)	−0.005 (2)	0.004 (2)	0.002 (2)
O6	0.042 (3)	0.066 (3)	0.018 (2)	−0.003 (2)	−0.001 (2)	−0.002 (2)
O7	0.066 (4)	0.038 (3)	0.022 (2)	−0.007 (3)	0.007 (2)	−0.002 (2)
O8	0.043 (3)	0.029 (2)	0.024 (2)	−0.003 (2)	0.012 (2)	0.0015 (19)
O9	0.069 (4)	0.034 (3)	0.018 (2)	−0.009 (2)	0.014 (2)	−0.0050 (19)
O10	0.065 (3)	0.027 (2)	0.022 (2)	−0.013 (2)	0.017 (2)	0.0012 (19)
O11	0.046 (3)	0.049 (3)	0.043 (3)	0.000 (2)	−0.005 (2)	−0.003 (2)
O12	0.046 (3)	0.100 (4)	0.032 (3)	0.019 (3)	0.009 (2)	0.023 (3)
O13	0.050 (3)	0.046 (3)	0.053 (3)	0.003 (2)	0.016 (2)	−0.005 (2)
O14	0.143 (7)	0.134 (5)	0.076 (4)	0.021 (5)	0.033 (4)	0.015 (4)
O15	0.054 (4)	0.061 (3)	0.114 (5)	−0.002 (3)	0.003 (3)	−0.003 (3)
O16	0.085 (5)	0.069 (3)	0.092 (4)	−0.007 (3)	0.014 (3)	−0.041 (3)
O17	0.297 (13)	0.352 (13)	0.105 (6)	0.155 (11)	0.000 (7)	−0.011 (8)
O18	0.451 (18)	0.077 (5)	0.236 (10)	0.052 (7)	−0.226 (11)	−0.008 (6)
O19	0.199 (10)	0.115 (6)	0.277 (12)	−0.027 (7)	0.002 (8)	0.010 (7)
O20	0.194 (8)	0.105 (5)	0.160 (7)	−0.032 (5)	0.098 (6)	−0.042 (5)

Ca1—O12	2.327 (4)	C13—O6	1.250 (6)
Ca1—O11	2.367 (4)	C13—O7	1.269 (6)
Ca1—O5	2.368 (4)	C13—C14	1.492 (8)
Ca1—O9	2.395 (4)	C14—C15	1.403 (7)
Ca1—O13	2.401 (4)	C14—C19	1.425 (7)
Ca1—O4	2.422 (4)	C15—C16	1.384 (8)
Ca1—O8	2.423 (4)	C15—H15	0.93
Ca1—H11A	2.7672	C16—C17	1.372 (8)
Ca1—H11C	2.7894	C16—H16	0.93
Cu1—O2	1.911 (4)	C17—C18	1.368 (7)
Cu1—N2	1.917 (4)	C17—H17	0.93
Cu1—N3	1.943 (5)	C18—C19	1.384 (7)
Cu1—O3	1.962 (4)	C18—H18	0.93
Cu2—O7	1.887 (4)	C20—O8	1.234 (6)
Cu2—N1	1.934 (4)	C20—C21	1.533 (7)
Cu2—N5	1.943 (5)	C21—O9	1.240 (6)
Cu2—O10	1.955 (4)	C21—O10	1.260 (6)
N1—C20	1.332 (6)	N5—C24	1.311 (7)
N1—C19	1.409 (6)	N5—C22	1.367 (7)
N2—C8	1.340 (6)	C22—C23	1.342 (8)
N2—C7	1.409 (6)	C22—H22	0.93
C1—O1	1.257 (7)	C23—N6	1.358 (8)
C1—O2	1.266 (7)	C23—H23	0.93
C1—C2	1.473 (8)	N6—C24	1.313 (7)
C2—C3	1.383 (7)	N6—H6A	0.86
C2—C7	1.406 (7)	C24—H24	0.93
C3—C4	1.352 (8)	O11—H11A	0.85
C3—H3	0.93	O11—H11C	0.85
C4—C5	1.385 (8)	O12—H12A	0.85
C4—H4	0.93	O12—H12B	0.85
C5—C6	1.369 (7)	O13—H13A	0.85
C5—H5	0.93	O13—H13B	0.85
C6—C7	1.390 (7)	O14—H14C	0.85
C6—H6	0.93	O14—H14D	0.85
C8—O5	1.237 (6)	O15—H15A	0.85
C8—C9	1.526 (7)	O15—H15D	0.85
C9—O4	1.241 (6)	O16—H16A	0.85
C9—O3	1.268 (6)	O16—H16B	0.85
N3—C10	1.305 (8)	O17—H17C	0.85
N3—C12	1.371 (8)	O17—H17D	0.85
C10—N4	1.316 (8)	O18—H18C	0.85
C10—H10	0.93	O18—H18D	0.85
N4—C11	1.344 (10)	O19—H19C	0.85
N4—H4A	0.86	O19—H19D	0.85
C11—C12	1.326 (10)	O20—H20C	0.85
C11—H11	0.93	O20—H20D	0.85
C12—H12	0.93
O12—Ca1—O11	176.97 (14)	C10—N3—C12	104.7 (6)
O12—Ca1—O5	79.88 (14)	C10—N3—Cu1	128.2 (5)
O11—Ca1—O5	103.11 (15)	C12—N3—Cu1	127.0 (6)
O12—Ca1—O9	92.60 (16)	N3—C10—N4	111.3 (8)
O11—Ca1—O9	85.50 (15)	N3—C10—H10	124.3
O5—Ca1—O9	137.32 (14)	N4—C10—H10	124.3
O12—Ca1—O13	97.38 (15)	C10—N4—C11	107.9 (7)
O11—Ca1—O13	82.84 (14)	C10—N4—H4A	126.0
O5—Ca1—O13	78.91 (14)	C11—N4—H4A	126.0
O9—Ca1—O13	143.71 (14)	C12—C11—N4	106.2 (8)
O12—Ca1—O4	98.41 (16)	C12—C11—H11	126.9
O11—Ca1—O4	83.26 (14)	N4—C11—H11	126.9
O5—Ca1—O4	67.80 (13)	C11—C12—N3	109.8 (8)
O9—Ca1—O4	71.98 (13)	C11—C12—H12	125.1
O13—Ca1—O4	139.70 (15)	N3—C12—H12	125.1
O12—Ca1—O8	79.15 (14)	O6—C13—O7	120.3 (6)
O11—Ca1—O8	97.93 (14)	O6—C13—C14	118.4 (6)
O5—Ca1—O8	148.21 (13)	O7—C13—C14	121.3 (5)
O9—Ca1—O8	67.35 (12)	C15—C14—C19	117.6 (5)
O13—Ca1—O8	80.40 (13)	C15—C14—C13	115.7 (5)
O4—Ca1—O8	139.05 (14)	C19—C14—C13	126.7 (5)
O12—Ca1—H11A	161.2	C16—C15—C14	122.7 (6)
O11—Ca1—H11A	16.8	C16—C15—H15	118.6
O5—Ca1—H11A	110.2	C14—C15—H15	118.6
O9—Ca1—H11A	90.1	C17—C16—C15	118.1 (6)
O13—Ca1—H11A	70.2	C17—C16—H16	121.0
O4—Ca1—H11A	100.1	C15—C16—H16	121.0
O8—Ca1—H11A	84.8	C18—C17—C16	121.1 (6)
O12—Ca1—H11C	162.1	C18—C17—H17	119.5
O11—Ca1—H11C	16.5	C16—C17—H17	119.5
O5—Ca1—H11C	111.4	C17—C18—C19	122.3 (6)
O9—Ca1—H11C	69.6	C17—C18—H18	118.9
O13—Ca1—H11C	98.5	C19—C18—H18	118.9
O4—Ca1—H11C	74.5	C18—C19—N1	122.1 (5)
O8—Ca1—H11C	95.3	C18—C19—C14	118.1 (5)
H11A—Ca1—H11C	28.9	N1—C19—C14	119.6 (5)
O2—Cu1—N2	92.99 (18)	O8—C20—N1	130.6 (5)
O2—Cu1—N3	91.0 (2)	O8—C20—C21	117.1 (5)
N2—Cu1—N3	173.2 (2)	N1—C20—C21	112.3 (5)
O2—Cu1—O3	166.89 (19)	O9—C21—O10	124.5 (5)
N2—Cu1—O3	85.94 (17)	O9—C21—C20	117.6 (5)
N3—Cu1—O3	91.3 (2)	O10—C21—C20	117.9 (5)
O7—Cu2—N1	95.17 (17)	C24—N5—C22	105.5 (5)
O7—Cu2—N5	89.76 (18)	C24—N5—Cu2	125.9 (4)
N1—Cu2—N5	173.9 (2)	C22—N5—Cu2	128.4 (4)
O7—Cu2—O10	176.73 (19)	C23—C22—N5	108.5 (6)
N1—Cu2—O10	85.29 (16)	C23—C22—H22	125.8
N5—Cu2—O10	89.59 (18)	N5—C22—H22	125.8
C20—N1—C19	122.6 (5)	C22—C23—N6	107.3 (6)
C20—N1—Cu2	112.2 (4)	C22—C23—H23	126.4
C19—N1—Cu2	125.2 (3)	N6—C23—H23	126.4
C8—N2—C7	122.2 (5)	C24—N6—C23	106.6 (6)
C8—N2—Cu1	112.1 (4)	C24—N6—H6A	126.7
C7—N2—Cu1	125.7 (4)	C23—N6—H6A	126.7
O1—C1—O2	119.1 (6)	N5—C24—N6	112.2 (6)
O1—C1—C2	118.0 (6)	N5—C24—H24	123.9
O2—C1—C2	122.9 (5)	N6—C24—H24	123.9
C3—C2—C7	117.9 (6)	C1—O2—Cu1	128.7 (4)
C3—C2—C1	117.0 (5)	C9—O3—Cu1	110.6 (3)
C7—C2—C1	125.1 (5)	C9—O4—Ca1	117.6 (4)
C4—C3—C2	123.1 (6)	C8—O5—Ca1	119.5 (3)
C4—C3—H3	118.5	C13—O7—Cu2	128.9 (4)
C2—C3—H3	118.5	C20—O8—Ca1	118.6 (3)
C3—C4—C5	119.0 (6)	C21—O9—Ca1	119.1 (4)
C3—C4—H4	120.5	C21—O10—Cu2	111.4 (3)
C5—C4—H4	120.5	Ca1—O11—H11A	109.4
C6—C5—C4	120.0 (6)	Ca1—O11—H11C	111.2
C6—C5—H5	120.0	H11A—O11—H11C	109.3
C4—C5—H5	120.0	Ca1—O12—H12A	134.4
C5—C6—C7	121.1 (6)	Ca1—O12—H12B	116.8
C5—C6—H6	119.4	H12A—O12—H12B	104.4
C7—C6—H6	119.4	Ca1—O13—H13A	109.8
C6—C7—C2	118.9 (5)	Ca1—O13—H13B	109.7
C6—C7—N2	121.2 (5)	H13A—O13—H13B	109.7
C2—C7—N2	119.8 (5)	H14C—O14—H14D	118.3
O5—C8—N2	129.7 (5)	H15A—O15—H15D	97.9
O5—C8—C9	117.7 (5)	H16A—O16—H16B	104.7
N2—C8—C9	112.6 (5)	H17C—O17—H17D	106.1
O4—C9—O3	124.6 (5)	H18C—O18—H18D	120.4
O4—C9—C8	117.4 (5)	H19C—O19—H19D	103.5
O3—C9—C8	118.1 (5)	H20C—O20—H20D	114.5

D—H···A	D—H	H···A	D···A	D—H···A
O20—H20D···O2i	0.85	2.11	2.950 (7)	172
O20—H20C···O19	0.85	2.09	2.749 (11)	134
O19—H19D···O18	0.85	2.34	2.887 (12)	123
O19—H19C···O17ii	0.85	1.91	2.758 (11)	180
O18—H18D···O6	0.85	2.50	3.070 (7)	125
O18—H18D···O7	0.85	2.20	3.049 (7)	179
O18—H18C···O14iii	0.85	2.04	2.887 (10)	178
O17—H17C···O14iv	0.85	2.17	2.974 (12)	158
O16—H16A···O10	0.85	2.10	2.850 (6)	148
O15—H15D···O16	0.85	2.01	2.845 (7)	167
O15—H15A···O9	0.85	2.42	3.131 (6)	141
O15—H15A···O4	0.85	2.38	3.121 (7)	146
O14—H14D···O15	0.85	2.08	2.798 (7)	142
O14—H14C···O3	0.85	2.21	3.045 (7)	169
O13—H13B···O19v	0.85	2.15	2.963 (9)	160
O13—H13A···O6vi	0.85	1.95	2.780 (6)	164
O12—H12B···O1vii	0.85	1.86	2.706 (6)	180
O12—H12A···O6v	0.85	1.87	2.725 (5)	180
O11—H11C···O15ii	0.85	2.37	2.778 (6)	110
O11—H11A···O1viii	0.85	1.96	2.780 (6)	163
N6—H6A···O9iii	0.86	2.13	2.958 (7)	161
N6—H6A···O4iii	0.86	2.48	3.018 (6)	122
N4—H4A···O20iii	0.86	2.03	2.888 (9)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O20—H20D⋯O2i	0.85	2.11	2.950 (7)	172
O20—H20C⋯O19	0.85	2.09	2.749 (11)	134
O19—H19D⋯O18	0.85	2.34	2.887 (12)	123
O19—H19C⋯O17ii	0.85	1.91	2.758 (11)	180
O18—H18D⋯O6	0.85	2.50	3.070 (7)	125
O18—H18D⋯O7	0.85	2.20	3.049 (7)	179
O18—H18C⋯O14iii	0.85	2.04	2.887 (10)	178
O17—H17C⋯O14iv	0.85	2.17	2.974 (12)	158
O16—H16A⋯O10	0.85	2.10	2.850 (6)	148
O15—H15D⋯O16	0.85	2.01	2.845 (7)	167
O15—H15A⋯O9	0.85	2.42	3.131 (6)	141
O15—H15A⋯O4	0.85	2.38	3.121 (7)	146
O14—H14D⋯O15	0.85	2.08	2.798 (7)	142
O14—H14C⋯O3	0.85	2.21	3.045 (7)	169
O13—H13B⋯O19v	0.85	2.15	2.963 (9)	160
O13—H13A⋯O6vi	0.85	1.95	2.780 (6)	164
O12—H12B⋯O1vii	0.85	1.86	2.706 (6)	180
O12—H12A⋯O6v	0.85	1.87	2.725 (5)	180
O11—H11C⋯O15ii	0.85	2.37	2.778 (6)	110
O11—H11A⋯O1viii	0.85	1.96	2.780 (6)	163
N6—H6A⋯O9iii	0.86	2.13	2.958 (7)	161
N6—H6A⋯O4iii	0.86	2.48	3.018 (6)	122
N4—H4A⋯O20iii	0.86	2.03	2.888 (9)	178

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .