(μ-3-Acetyl-5-carboxyl-ato-4-methyl-pyrazolido-1:2κN,O:N,O)-μ-chlorido-tetra-pyridine-1κN,2κN-chlorido-1κCl-dicopper(II) propan-2-ol solvate.

The title compound, [Cu(2)(C(7)H(6)N(2)O(3))Cl(2)(C(5)H(5)N)(4)]·C(3)H(8)O, is a binuclear pyrazolate complex, in which the two Cu(II) atoms have different coordination numbers and are connected by a bridging Cl atom. One Cu(II) atom has a distorted square-pyramidal coordination environment formed by two pyridine N atoms, one bridging Cl atom and an N,O-chelating pyrazolate ligand. The other Cu(II) atom adopts an octa-hedral geometry defined by two pyridine N atoms at the axial positions, two Cl atoms and the coordinated pyrazolate ligand in the equatorial plane. An O-H⋯O hydrogen bond connects the complex mol-ecules and propan-2-ol solvent mol-ecules into pairs. These pairs form columns along the a axis.

Related literature

For other 3,5-substituted-1H-pyrazolate complexes, see: Driessen et al. (2003 ▶); Eisenwiener et al. (2007 ▶); King et al. (2004 ▶); Li (2005 ▶); Penkova et al. (2008 ▶); Tretyakov et al. (2008 ▶).

Experimental

Crystal data

[Cu2(C7H6N2O3)Cl2(C5H5N)4]·C3H8O

M = 740.61

Monoclinic,

a = 16.4130 (4) Å

b = 12.6351 (2) Å

c = 16.5739 (4) Å

β = 107.2145 (12)°

V = 3283.12 (12) Å3

Z = 4

Mo Kα radiation

μ = 1.50 mm−1

T = 100 K

0.24 × 0.16 × 0.13 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.718, T max = 0.832

45344 measured reflections

8719 independent reflections

6355 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.086

S = 1.03

8719 reflections

402 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.47 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038276/hy2229sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038276/hy2229Isup2.hkl

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

[Cu2(C7H6N2O3)Cl2(C5H5N)4]·C3H8O	F(000) = 1520
Mr = 740.61	Dx = 1.498 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14278 reflections
a = 16.4130 (4) Å	θ = 1.0–30.0°
b = 12.6351 (2) Å	µ = 1.50 mm−1
c = 16.5739 (4) Å	T = 100 K
β = 107.2145 (12)°	Block, green-blue
V = 3283.12 (12) Å3	0.24 × 0.16 × 0.13 mm
Z = 4

Nonius KappaCCD diffractometer	8719 independent reflections
Radiation source: fine-focus sealed tube	6355 reflections with I > 2σ(I)
horizontally mounted graphite crystal	Rint = 0.058
Detector resolution: 9 pixels mm-1	θmax = 29.0°, θmin = 2.6°
φ and ω scans with κ offset	h = −22→22
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −17→17
Tmin = 0.718, Tmax = 0.832	l = −21→22
45344 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0362P)2 + 1.5874P] where P = (Fo2 + 2Fc2)/3
8719 reflections	(Δ/σ)max = 0.001
402 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

	x	y	z	Uiso*/Ueq
Cu1	0.152430 (17)	−0.09197 (2)	0.372827 (16)	0.01651 (7)
Cu2	0.227801 (17)	0.202366 (19)	0.406284 (16)	0.01633 (7)
Cl1	0.03110 (3)	−0.17696 (4)	0.37302 (3)	0.02075 (12)
Cl2	0.09566 (3)	0.12326 (4)	0.35994 (3)	0.01988 (12)
O1	0.25807 (11)	−0.24098 (12)	0.36521 (10)	0.0256 (4)
O2	0.34674 (10)	0.26096 (12)	0.42092 (9)	0.0216 (3)
O3	0.47931 (11)	0.21282 (13)	0.42382 (11)	0.0305 (4)
H3O	0.5189	0.2845	0.3481	0.046*
O4	0.55635 (13)	0.32508 (17)	0.32569 (13)	0.0460 (5)
N1	0.26482 (11)	−0.02909 (13)	0.37947 (11)	0.0167 (4)
N2	0.28640 (12)	0.07195 (13)	0.39256 (11)	0.0165 (4)
N3	0.12367 (12)	−0.10132 (14)	0.24327 (11)	0.0181 (4)
N4	0.18472 (12)	−0.08623 (13)	0.50126 (11)	0.0186 (4)
N5	0.18432 (12)	0.35174 (14)	0.38697 (11)	0.0191 (4)
N6	0.24312 (12)	0.20815 (14)	0.54257 (11)	0.0207 (4)
C1	0.33529 (14)	−0.08399 (17)	0.37618 (13)	0.0179 (4)
C2	0.32611 (15)	−0.19962 (17)	0.36623 (14)	0.0208 (5)
C3	0.40018 (16)	−0.26389 (19)	0.36067 (16)	0.0293 (6)
H3A	0.3827	−0.3380	0.3498	0.044*
H3B	0.4462	−0.2588	0.4140	0.044*
H3C	0.4204	−0.2372	0.3145	0.044*
C4	0.40414 (14)	−0.01443 (18)	0.38640 (13)	0.0202 (5)
C5	0.49426 (15)	−0.0362 (2)	0.38719 (15)	0.0266 (5)
H5A	0.5251	0.0308	0.3904	0.040*
H5B	0.4941	−0.0738	0.3354	0.040*
H5C	0.5225	−0.0800	0.4363	0.040*
C6	0.36967 (14)	0.08353 (17)	0.39700 (13)	0.0180 (5)
C7	0.40334 (15)	0.19301 (18)	0.41462 (13)	0.0210 (5)
C8	0.09276 (14)	−0.19093 (17)	0.20156 (14)	0.0205 (5)
H8	0.0852	−0.2509	0.2332	0.025*
C9	0.07149 (15)	−0.19954 (18)	0.11467 (15)	0.0240 (5)
H9	0.0503	−0.2644	0.0874	0.029*
C10	0.08148 (16)	−0.1127 (2)	0.06806 (15)	0.0275 (5)
H10	0.0667	−0.1163	0.0082	0.033*
C11	0.11359 (16)	−0.02000 (19)	0.11047 (15)	0.0290 (6)
H11	0.1212	0.0411	0.0801	0.035*
C12	0.13440 (15)	−0.01797 (18)	0.19762 (15)	0.0236 (5)
H12	0.1573	0.0454	0.2264	0.028*
C13	0.13414 (15)	−0.03639 (17)	0.53964 (14)	0.0220 (5)
H13	0.0846	−0.0015	0.5056	0.026*
C14	0.15093 (16)	−0.03359 (19)	0.62622 (15)	0.0276 (6)
H14	0.1138	0.0029	0.6511	0.033*
C15	0.22260 (18)	−0.0847 (2)	0.67623 (16)	0.0328 (6)
H15	0.2354	−0.0844	0.7360	0.039*
C16	0.27560 (17)	−0.1365 (2)	0.63733 (16)	0.0335 (6)
H16	0.3254	−0.1721	0.6701	0.040*
C17	0.25461 (16)	−0.13519 (19)	0.55032 (15)	0.0264 (5)
H17	0.2911	−0.1704	0.5240	0.032*
C18	0.23103 (16)	0.42893 (18)	0.43517 (14)	0.0247 (5)
H18	0.2827	0.4103	0.4767	0.030*
C19	0.20695 (16)	0.53372 (17)	0.42661 (15)	0.0261 (5)
H19	0.2411	0.5861	0.4621	0.031*
C20	0.13255 (16)	0.56161 (18)	0.36572 (14)	0.0241 (5)
H20	0.1146	0.6334	0.3588	0.029*
C21	0.08464 (14)	0.48361 (17)	0.31503 (14)	0.0202 (5)
H21	0.0335	0.5009	0.2722	0.024*
C22	0.11246 (14)	0.37959 (17)	0.32779 (13)	0.0183 (5)
H22	0.0792	0.3259	0.2931	0.022*
C23	0.31973 (18)	0.1915 (2)	0.59788 (16)	0.0394 (7)
H23	0.3664	0.1773	0.5767	0.047*
C24	0.33449 (19)	0.1939 (3)	0.68440 (16)	0.0445 (8)
H24	0.3899	0.1810	0.7217	0.053*
C25	0.26752 (18)	0.2153 (2)	0.71528 (16)	0.0342 (6)
H25	0.2755	0.2164	0.7744	0.041*
C26	0.18849 (16)	0.23518 (19)	0.65927 (15)	0.0273 (5)
H26	0.1414	0.2526	0.6791	0.033*
C27	0.17882 (15)	0.22930 (17)	0.57336 (14)	0.0214 (5)
H27	0.1238	0.2409	0.5349	0.026*
C28	0.6574 (2)	0.4623 (3)	0.3462 (2)	0.0615 (10)
H28A	0.7052	0.4127	0.3547	0.092*
H28B	0.6775	0.5276	0.3776	0.092*
H28C	0.6342	0.4785	0.2859	0.092*
C29	0.58876 (19)	0.4128 (2)	0.37756 (18)	0.0424 (7)
H29	0.6153	0.3871	0.4366	0.051*
C30	0.5193 (3)	0.4877 (3)	0.3776 (3)	0.0765 (12)
H30A	0.4981	0.5210	0.3219	0.115*
H30B	0.5411	0.5422	0.4206	0.115*
H30C	0.4727	0.4492	0.3903	0.115*

	U11	U22	U33	U12	U13	U23
Cu1	0.01760 (15)	0.01758 (14)	0.01463 (14)	−0.00056 (10)	0.00519 (11)	−0.00005 (10)
Cu2	0.01967 (15)	0.01512 (13)	0.01380 (14)	0.00081 (10)	0.00435 (11)	−0.00014 (10)
Cl1	0.0200 (3)	0.0225 (3)	0.0202 (3)	−0.0027 (2)	0.0066 (2)	0.0001 (2)
Cl2	0.0195 (3)	0.0164 (2)	0.0236 (3)	0.0010 (2)	0.0061 (2)	0.0000 (2)
O1	0.0276 (10)	0.0197 (8)	0.0289 (9)	0.0014 (7)	0.0077 (8)	−0.0007 (7)
O2	0.0233 (9)	0.0209 (8)	0.0198 (8)	−0.0023 (7)	0.0049 (7)	−0.0015 (6)
O3	0.0215 (9)	0.0342 (9)	0.0352 (10)	−0.0071 (7)	0.0076 (8)	−0.0003 (8)
O4	0.0422 (12)	0.0577 (13)	0.0413 (12)	−0.0113 (10)	0.0171 (10)	−0.0037 (10)
N1	0.0183 (10)	0.0164 (9)	0.0145 (9)	0.0024 (7)	0.0036 (8)	0.0000 (7)
N2	0.0176 (10)	0.0176 (9)	0.0139 (9)	−0.0010 (7)	0.0039 (7)	0.0000 (7)
N3	0.0175 (10)	0.0202 (9)	0.0170 (9)	0.0015 (7)	0.0055 (8)	0.0003 (7)
N4	0.0209 (10)	0.0178 (9)	0.0172 (9)	−0.0029 (7)	0.0057 (8)	0.0006 (7)
N5	0.0263 (11)	0.0173 (9)	0.0134 (9)	0.0013 (8)	0.0053 (8)	0.0004 (7)
N6	0.0218 (10)	0.0239 (10)	0.0162 (9)	0.0068 (8)	0.0052 (8)	0.0009 (7)
C1	0.0181 (11)	0.0231 (11)	0.0119 (10)	0.0032 (9)	0.0037 (9)	−0.0011 (8)
C2	0.0244 (13)	0.0216 (11)	0.0148 (11)	0.0051 (10)	0.0034 (9)	−0.0008 (9)
C3	0.0271 (14)	0.0269 (12)	0.0322 (14)	0.0080 (10)	0.0061 (11)	−0.0076 (10)
C4	0.0195 (12)	0.0276 (12)	0.0132 (11)	0.0024 (9)	0.0044 (9)	0.0003 (9)
C5	0.0177 (12)	0.0361 (14)	0.0256 (13)	0.0032 (10)	0.0061 (10)	−0.0036 (10)
C6	0.0196 (12)	0.0230 (11)	0.0112 (10)	0.0000 (9)	0.0042 (9)	0.0001 (8)
C7	0.0218 (13)	0.0269 (12)	0.0128 (11)	−0.0027 (10)	0.0029 (9)	0.0034 (9)
C8	0.0229 (12)	0.0190 (11)	0.0204 (11)	0.0013 (9)	0.0077 (10)	0.0005 (9)
C9	0.0236 (13)	0.0240 (12)	0.0252 (12)	−0.0005 (10)	0.0085 (10)	−0.0066 (10)
C10	0.0279 (14)	0.0381 (14)	0.0177 (12)	−0.0016 (11)	0.0085 (10)	−0.0013 (10)
C11	0.0365 (15)	0.0288 (13)	0.0214 (12)	−0.0064 (11)	0.0083 (11)	0.0038 (10)
C12	0.0256 (13)	0.0231 (12)	0.0232 (12)	−0.0044 (10)	0.0087 (10)	0.0002 (9)
C13	0.0265 (13)	0.0188 (11)	0.0218 (12)	0.0001 (9)	0.0088 (10)	0.0011 (9)
C14	0.0382 (16)	0.0264 (12)	0.0223 (12)	−0.0020 (11)	0.0151 (12)	−0.0036 (10)
C15	0.0403 (16)	0.0418 (15)	0.0165 (12)	−0.0052 (12)	0.0084 (11)	−0.0013 (11)
C16	0.0316 (15)	0.0447 (16)	0.0214 (13)	0.0066 (12)	0.0035 (11)	0.0069 (11)
C17	0.0242 (13)	0.0336 (13)	0.0209 (12)	0.0032 (10)	0.0060 (10)	−0.0003 (10)
C18	0.0301 (14)	0.0225 (12)	0.0172 (11)	−0.0003 (10)	0.0002 (10)	−0.0012 (9)
C19	0.0363 (15)	0.0171 (11)	0.0219 (12)	−0.0024 (10)	0.0040 (11)	−0.0043 (9)
C20	0.0356 (14)	0.0169 (11)	0.0236 (12)	0.0017 (10)	0.0146 (11)	0.0046 (9)
C21	0.0192 (12)	0.0238 (11)	0.0189 (11)	0.0024 (9)	0.0076 (9)	0.0055 (9)
C22	0.0194 (12)	0.0206 (11)	0.0157 (11)	−0.0024 (9)	0.0064 (9)	−0.0002 (8)
C23	0.0300 (15)	0.072 (2)	0.0174 (13)	0.0209 (14)	0.0083 (11)	0.0048 (13)
C24	0.0322 (16)	0.080 (2)	0.0190 (13)	0.0164 (15)	0.0046 (12)	0.0038 (14)
C25	0.0401 (16)	0.0475 (16)	0.0159 (12)	−0.0050 (13)	0.0095 (12)	−0.0070 (11)
C26	0.0268 (14)	0.0343 (13)	0.0254 (13)	−0.0073 (11)	0.0147 (11)	−0.0083 (10)
C27	0.0211 (12)	0.0210 (11)	0.0220 (12)	−0.0021 (9)	0.0064 (10)	−0.0022 (9)
C28	0.063 (2)	0.090 (3)	0.0310 (17)	−0.040 (2)	0.0120 (16)	−0.0058 (17)
C29	0.0398 (17)	0.0536 (18)	0.0330 (16)	−0.0096 (14)	0.0097 (13)	−0.0041 (13)
C30	0.082 (3)	0.056 (2)	0.095 (3)	0.008 (2)	0.030 (2)	−0.010 (2)

Cu1—N1	1.9814 (18)	C9—H9	0.9500
Cu1—N3	2.0609 (18)	C10—C11	1.387 (3)
Cu1—N4	2.0371 (18)	C10—H10	0.9500
Cu1—O1	2.5878 (17)	C11—C12	1.383 (3)
Cu1—Cl1	2.2634 (6)	C11—H11	0.9500
Cu1—Cl2	2.8621 (6)	C12—H12	0.9500
Cu2—N2	1.9549 (18)	C13—C14	1.379 (3)
Cu2—N5	2.0097 (18)	C13—H13	0.9500
Cu2—N6	2.1987 (18)	C14—C15	1.382 (4)
Cu2—O2	2.0340 (16)	C14—H14	0.9500
Cu2—Cl2	2.3036 (6)	C15—C16	1.390 (4)
O1—C2	1.229 (3)	C15—H15	0.9500
O2—C7	1.292 (3)	C16—C17	1.380 (3)
O3—C7	1.236 (3)	C16—H16	0.9500
O4—C29	1.407 (3)	C17—H17	0.9500
O4—H3O	0.9550	C18—C19	1.377 (3)
N1—N2	1.325 (2)	C18—H18	0.9500
N1—C1	1.364 (3)	C19—C20	1.380 (3)
N2—C6	1.355 (3)	C19—H19	0.9500
N3—C12	1.338 (3)	C20—C21	1.380 (3)
N3—C8	1.345 (3)	C20—H20	0.9500
N4—C13	1.343 (3)	C21—C22	1.387 (3)
N4—C17	1.344 (3)	C21—H21	0.9500
N5—C22	1.339 (3)	C22—H22	0.9500
N5—C18	1.347 (3)	C23—C24	1.382 (4)
N6—C27	1.328 (3)	C23—H23	0.9500
N6—C23	1.335 (3)	C24—C25	1.370 (4)
C1—C4	1.402 (3)	C24—H24	0.9500
C1—C2	1.473 (3)	C25—C26	1.376 (4)
C2—C3	1.487 (3)	C25—H25	0.9500
C3—H3A	0.9800	C26—C27	1.387 (3)
C3—H3B	0.9800	C26—H26	0.9500
C3—H3C	0.9800	C27—H27	0.9500
C4—C6	1.393 (3)	C28—C29	1.509 (4)
C4—C5	1.501 (3)	C28—H28A	0.9800
C5—H5A	0.9800	C28—H28B	0.9800
C5—H5B	0.9800	C28—H28C	0.9800
C5—H5C	0.9800	C29—C30	1.482 (5)
C6—C7	1.486 (3)	C29—H29	1.0000
C8—C9	1.382 (3)	C30—H30A	0.9800
C8—H8	0.9500	C30—H30B	0.9800
C9—C10	1.379 (3)	C30—H30C	0.9800
N1—Cu1—N4	88.72 (7)	C10—C9—C8	119.1 (2)
N1—Cu1—N3	90.19 (7)	C10—C9—H9	120.5
N4—Cu1—N3	177.86 (7)	C8—C9—H9	120.5
N1—Cu1—Cl1	174.40 (5)	C9—C10—C11	118.6 (2)
N4—Cu1—Cl1	88.41 (5)	C9—C10—H10	120.7
N3—Cu1—Cl1	92.52 (5)	C11—C10—H10	120.7
N1—Cu1—O1	70.62 (7)	C12—C11—C10	119.0 (2)
N3—Cu1—O1	81.82 (6)	C12—C11—H11	120.5
N4—Cu1—O1	96.09 (6)	C10—C11—H11	120.5
Cl1—Cu1—O1	104.91 (4)	N3—C12—C11	122.9 (2)
Cl2—Cu1—O1	153.60 (4)	N3—C12—H12	118.6
N1—Cu1—Cl2	84.28 (5)	C11—C12—H12	118.6
N3—Cu1—Cl2	90.44 (5)	N4—C13—C14	122.9 (2)
N4—Cu1—Cl2	91.29 (5)	N4—C13—H13	118.5
Cl1—Cu1—Cl2	100.59 (2)	C14—C13—H13	118.5
N2—Cu2—N5	159.53 (7)	C13—C14—C15	119.0 (2)
N2—Cu2—O2	80.38 (7)	C13—C14—H14	120.5
N5—Cu2—O2	87.72 (7)	C15—C14—H14	120.5
N2—Cu2—N6	103.71 (7)	C14—C15—C16	118.7 (2)
N5—Cu2—N6	93.42 (7)	C14—C15—H15	120.7
O2—Cu2—N6	92.95 (7)	C16—C15—H15	120.7
N2—Cu2—Cl2	92.44 (5)	C17—C16—C15	118.8 (2)
N5—Cu2—Cl2	95.71 (6)	C17—C16—H16	120.6
O2—Cu2—Cl2	166.73 (5)	C15—C16—H16	120.6
N6—Cu2—Cl2	99.62 (5)	N4—C17—C16	122.8 (2)
C7—O2—Cu2	115.87 (14)	N4—C17—H17	118.6
C29—O4—H3O	110.8	C16—C17—H17	118.6
N2—N1—C1	107.93 (18)	N5—C18—C19	122.6 (2)
N2—N1—Cu1	126.48 (14)	N5—C18—H18	118.7
C1—N1—Cu1	125.49 (14)	C19—C18—H18	118.7
N1—N2—C6	109.22 (17)	C18—C19—C20	119.1 (2)
N1—N2—Cu2	135.57 (15)	C18—C19—H19	120.5
C6—N2—Cu2	115.20 (14)	C20—C19—H19	120.5
C12—N3—C8	117.68 (19)	C21—C20—C19	119.0 (2)
C12—N3—Cu1	121.06 (15)	C21—C20—H20	120.5
C8—N3—Cu1	121.26 (15)	C19—C20—H20	120.5
C13—N4—C17	117.8 (2)	C20—C21—C22	118.8 (2)
C13—N4—Cu1	120.37 (15)	C20—C21—H21	120.6
C17—N4—Cu1	121.81 (15)	C22—C21—H21	120.6
C22—N5—C18	117.88 (19)	N5—C22—C21	122.7 (2)
C22—N5—Cu2	123.91 (15)	N5—C22—H22	118.7
C18—N5—Cu2	118.20 (15)	C21—C22—H22	118.7
C27—N6—C23	117.5 (2)	N6—C23—C24	123.3 (2)
C27—N6—Cu2	122.62 (15)	N6—C23—H23	118.3
C23—N6—Cu2	119.87 (16)	C24—C23—H23	118.3
N1—C1—C4	109.83 (19)	C25—C24—C23	118.6 (3)
N1—C1—C2	116.7 (2)	C25—C24—H24	120.7
C4—C1—C2	133.4 (2)	C23—C24—H24	120.7
O1—C2—C1	119.1 (2)	C24—C25—C26	119.0 (2)
O1—C2—C3	121.5 (2)	C24—C25—H25	120.5
C1—C2—C3	119.3 (2)	C26—C25—H25	120.5
C2—C3—H3A	109.5	C25—C26—C27	118.8 (2)
C2—C3—H3B	109.5	C25—C26—H26	120.6
H3A—C3—H3B	109.5	C27—C26—H26	120.6
C2—C3—H3C	109.5	N6—C27—C26	122.9 (2)
H3A—C3—H3C	109.5	N6—C27—H27	118.6
H3B—C3—H3C	109.5	C26—C27—H27	118.6
C6—C4—C1	103.25 (19)	C29—C28—H28A	109.5
C6—C4—C5	126.7 (2)	C29—C28—H28B	109.5
C1—C4—C5	130.0 (2)	H28A—C28—H28B	109.5
C4—C5—H5A	109.5	C29—C28—H28C	109.5
C4—C5—H5B	109.5	H28A—C28—H28C	109.5
H5A—C5—H5B	109.5	H28B—C28—H28C	109.5
C4—C5—H5C	109.5	O4—C29—C30	110.6 (3)
H5A—C5—H5C	109.5	O4—C29—C28	107.5 (2)
H5B—C5—H5C	109.5	C30—C29—C28	112.9 (3)
N2—C6—C4	109.76 (19)	O4—C29—H29	108.6
N2—C6—C7	114.94 (19)	C30—C29—H29	108.6
C4—C6—C7	135.3 (2)	C28—C29—H29	108.6
O3—C7—O2	125.4 (2)	C29—C30—H30A	109.5
O3—C7—C6	121.0 (2)	C29—C30—H30B	109.5
O2—C7—C6	113.6 (2)	H30A—C30—H30B	109.5
N3—C8—C9	122.8 (2)	C29—C30—H30C	109.5
N3—C8—H8	118.6	H30A—C30—H30C	109.5
C9—C8—H8	118.6	H30B—C30—H30C	109.5
N2—Cu2—O2—C7	0.53 (15)	C4—C1—C2—C3	−3.8 (4)
N5—Cu2—O2—C7	−162.76 (15)	N1—C1—C4—C6	0.8 (2)
N6—Cu2—O2—C7	103.94 (15)	C2—C1—C4—C6	−176.6 (2)
Cl2—Cu2—O2—C7	−57.4 (3)	N1—C1—C4—C5	−179.8 (2)
N4—Cu1—N1—N2	−78.06 (17)	C2—C1—C4—C5	2.8 (4)
N3—Cu1—N1—N2	103.78 (17)	N1—N2—C6—C4	−0.1 (2)
N4—Cu1—N1—C1	97.87 (17)	Cu2—N2—C6—C4	179.96 (14)
N3—Cu1—N1—C1	−80.29 (17)	N1—N2—C6—C7	−177.94 (17)
C1—N1—N2—C6	0.6 (2)	Cu2—N2—C6—C7	2.1 (2)
Cu1—N1—N2—C6	177.10 (14)	C1—C4—C6—N2	−0.5 (2)
C1—N1—N2—Cu2	−179.44 (15)	C5—C4—C6—N2	−179.9 (2)
Cu1—N1—N2—Cu2	−2.9 (3)	C1—C4—C6—C7	176.8 (2)
N5—Cu2—N2—N1	−126.1 (2)	C5—C4—C6—C7	−2.6 (4)
O2—Cu2—N2—N1	178.6 (2)	Cu2—O2—C7—O3	−177.94 (17)
N6—Cu2—N2—N1	87.9 (2)	Cu2—O2—C7—C6	0.4 (2)
Cl2—Cu2—N2—N1	−12.64 (19)	N2—C6—C7—O3	176.8 (2)
N5—Cu2—N2—C6	53.8 (3)	C4—C6—C7—O3	−0.3 (4)
O2—Cu2—N2—C6	−1.45 (14)	N2—C6—C7—O2	−1.6 (3)
N6—Cu2—N2—C6	−92.15 (15)	C4—C6—C7—O2	−178.8 (2)
Cl2—Cu2—N2—C6	167.33 (14)	C12—N3—C8—C9	−0.5 (3)
N1—Cu1—N3—C12	−49.00 (18)	Cu1—N3—C8—C9	178.93 (17)
Cl1—Cu1—N3—C12	135.90 (17)	N3—C8—C9—C10	−0.6 (4)
N1—Cu1—N3—C8	131.61 (17)	C8—C9—C10—C11	0.8 (4)
Cl1—Cu1—N3—C8	−43.49 (17)	C9—C10—C11—C12	0.0 (4)
N1—Cu1—N4—C13	124.85 (17)	C8—N3—C12—C11	1.3 (3)
Cl1—Cu1—N4—C13	−59.96 (16)	Cu1—N3—C12—C11	−178.08 (18)
N1—Cu1—N4—C17	−57.93 (18)	C10—C11—C12—N3	−1.1 (4)
Cl1—Cu1—N4—C17	117.26 (17)	C17—N4—C13—C14	0.0 (3)
N2—Cu2—N5—C22	84.2 (3)	Cu1—N4—C13—C14	177.31 (17)
O2—Cu2—N5—C22	138.41 (18)	N4—C13—C14—C15	−0.4 (4)
N6—Cu2—N5—C22	−128.77 (18)	C13—C14—C15—C16	0.5 (4)
Cl2—Cu2—N5—C22	−28.74 (17)	C14—C15—C16—C17	−0.1 (4)
N2—Cu2—N5—C18	−94.3 (3)	C13—N4—C17—C16	0.4 (3)
O2—Cu2—N5—C18	−40.15 (17)	Cu1—N4—C17—C16	−176.94 (19)
N6—Cu2—N5—C18	52.67 (18)	C15—C16—C17—N4	−0.3 (4)
Cl2—Cu2—N5—C18	152.70 (16)	C22—N5—C18—C19	1.1 (3)
N2—Cu2—N6—C27	−133.26 (17)	Cu2—N5—C18—C19	179.71 (19)
N5—Cu2—N6—C27	58.05 (18)	N5—C18—C19—C20	−0.7 (4)
O2—Cu2—N6—C27	145.94 (17)	C18—C19—C20—C21	−0.2 (4)
Cl2—Cu2—N6—C27	−38.34 (17)	C19—C20—C21—C22	0.8 (3)
N2—Cu2—N6—C23	47.7 (2)	C18—N5—C22—C21	−0.4 (3)
N5—Cu2—N6—C23	−121.0 (2)	Cu2—N5—C22—C21	−179.01 (16)
O2—Cu2—N6—C23	−33.1 (2)	C20—C21—C22—N5	−0.5 (3)
Cl2—Cu2—N6—C23	142.7 (2)	C27—N6—C23—C24	0.9 (4)
N2—N1—C1—C4	−0.9 (2)	Cu2—N6—C23—C24	179.9 (2)
Cu1—N1—C1—C4	−177.46 (14)	N6—C23—C24—C25	−0.6 (5)
N2—N1—C1—C2	177.02 (17)	C23—C24—C25—C26	−1.0 (4)
Cu1—N1—C1—C2	0.5 (3)	C24—C25—C26—C27	2.1 (4)
N1—C1—C2—O1	−3.2 (3)	C23—N6—C27—C26	0.4 (3)
C4—C1—C2—O1	174.1 (2)	Cu2—N6—C27—C26	−178.65 (17)
N1—C1—C2—C3	178.91 (19)	C25—C26—C27—N6	−1.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H3O···O3	0.95	1.82	2.734 (3)	160

Table 1

Selected bond lengths (Å)

Cu1—N1	1.9814 (18)
Cu1—N3	2.0609 (18)
Cu1—N4	2.0371 (18)
Cu1—O1	2.5878 (17)
Cu1—Cl1	2.2634 (6)
Cu1—Cl2	2.8621 (6)
Cu2—N2	1.9549 (18)
Cu2—N5	2.0097 (18)
Cu2—N6	2.1987 (18)
Cu2—O2	2.0340 (16)
Cu2—Cl2	2.3036 (6)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H3O⋯O3	0.95	1.82	2.734 (3)	160