Tetra-kis(4-amino-pyridine-κN)dichlorido-copper(II) monohydrate.

The asymmetric unit of the title compound, [CuCl(2)(C(5)H(6)N(2))(4)]·H(2)O, contains two crystallographically independent complex mol-ecules and two water mol-ecules. The Cu(II) ion in each mol-ecule is six-coordinated in an elongated octa-hedral geometry, with the equatorial plane defined by four pyridine N atoms of four amino-pyridine ligands and the axial positions occupied by two Cl atoms. In the crystal structure, mol-ecules are linked into a three-dimensional framework by C-H⋯Cl, O-H⋯Cl, N-H⋯O, N-H⋯Cl and N-H⋯N hydrogen bonds and C/N-H⋯π inter-actions involving the pyridine rings.

Related literature

For related literature on 4-amino­pyridine, see: Judge & Bever (2006 ▶); Schwid et al. (1997 ▶); Strupp et al. (2004 ▶). For bond lengths, see: Moncol et al. (2004 ▶); Zaleski et al. (2005 ▶); Anderson et al. (2005 ▶).

Experimental

Crystal data

[CuCl2(C5H6N2)4]·H2O

M = 528.93

Triclinic,

a = 9.5430 (2) Å

b = 14.1606 (2) Å

c = 17.4662 (3) Å

α = 88.463 (1)°

β = 86.075 (1)°

γ = 85.781 (1)°

V = 2347.81 (7) Å3

Z = 4

Mo Kα radiation

μ = 1.19 mm−1

T = 100.0 (1) K

0.51 × 0.40 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.583, T max = 0.871

106511 measured reflections

24484 independent reflections

17417 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.104

S = 1.07

24484 reflections

593 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.92 e Å−3

Δρmin = −1.11 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808015778/ci2603sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015778/ci2603Isup2.hkl

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

[CuCl2(C5H6N2)4]·H2O	Z = 4
Mr = 528.93	F000 = 1092
Triclinic, P1	Dx = 1.496 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.5430 (2) Å	Cell parameters from 9885 reflections
b = 14.1606 (2) Å	θ = 2.5–34.6º
c = 17.4662 (3) Å	µ = 1.19 mm−1
α = 88.463 (1)º	T = 100.0 (1) K
β = 86.075 (1)º	Plate, purple
γ = 85.781 (1)º	0.51 × 0.40 × 0.12 mm
V = 2347.81 (7) Å3

Bruker SMART APEXII CCD area-detector diffractometer	24484 independent reflections
Radiation source: fine-focus sealed tube	17417 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.047
T = 100.0(1) K	θmax = 37.5º
φ and ω scans	θmin = 1.2º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −16→15
Tmin = 0.583, Tmax = 0.871	k = −23→24
106511 measured reflections	l = −29→29

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0446P)2 + 0.3682P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
24484 reflections	Δρmax = 0.92 e Å−3
593 parameters	Δρmin = −1.11 e Å−3
6 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Cu1	0.438175 (17)	0.078184 (11)	0.230903 (9)	0.01546 (4)
N1	0.42808 (11)	−0.05177 (8)	0.18839 (6)	0.01482 (18)
N2	0.37359 (14)	−0.31516 (8)	0.09807 (7)	0.0227 (2)
H2A	0.3669	−0.3204	0.0495	0.027*
H2B	0.3679	−0.3641	0.1281	0.027*
N3	0.58224 (11)	0.02793 (7)	0.30393 (6)	0.01460 (18)
N4	0.88631 (12)	−0.05810 (9)	0.45634 (7)	0.0204 (2)
H4A	0.9675	−0.0825	0.4396	0.025*
H4B	0.8678	−0.0508	0.5048	0.025*
N5	0.42913 (11)	0.20525 (7)	0.28145 (6)	0.01477 (18)
N6	0.40879 (14)	0.45962 (9)	0.39775 (8)	0.0280 (3)
H6A	0.3293	0.4829	0.4178	0.034*
H6B	0.4840	0.4882	0.4026	0.034*
N7	0.27731 (11)	0.12641 (8)	0.16710 (6)	0.01593 (19)
N8	−0.06992 (13)	0.23308 (10)	0.05134 (8)	0.0276 (3)
H8A	−0.0617	0.2769	0.0167	0.033*
H8B	−0.1504	0.2106	0.0623	0.033*
C1	0.41925 (13)	−0.06352 (9)	0.11226 (7)	0.0155 (2)
H1	0.4246	−0.0105	0.0799	0.019*
C2	0.40285 (13)	−0.14884 (9)	0.07986 (7)	0.0154 (2)
H2	0.3983	−0.1527	0.0270	0.018*
C3	0.39299 (13)	−0.23054 (9)	0.12703 (7)	0.0160 (2)
C4	0.40297 (14)	−0.21872 (9)	0.20635 (7)	0.0172 (2)
H4	0.3979	−0.2704	0.2401	0.021*
C5	0.42019 (13)	−0.13030 (9)	0.23353 (7)	0.0162 (2)
H5	0.4268	−0.1243	0.2860	0.019*
C6	0.70980 (14)	−0.01180 (9)	0.27928 (7)	0.0173 (2)
H6	0.7287	−0.0193	0.2268	0.021*
C7	0.81305 (14)	−0.04176 (10)	0.32694 (7)	0.0180 (2)
H7	0.8989	−0.0688	0.3067	0.022*
C8	0.78850 (13)	−0.03145 (9)	0.40679 (7)	0.0144 (2)
C9	0.65482 (13)	0.00904 (9)	0.43265 (7)	0.0158 (2)
H9	0.6324	0.0169	0.4849	0.019*
C10	0.55757 (13)	0.03684 (9)	0.38032 (7)	0.0159 (2)
H10	0.4700	0.0632	0.3987	0.019*
C11	0.54513 (13)	0.25191 (9)	0.28928 (8)	0.0175 (2)
H11	0.6310	0.2255	0.2685	0.021*
C12	0.54381 (14)	0.33629 (9)	0.32624 (8)	0.0190 (2)
H12	0.6270	0.3657	0.3300	0.023*
C13	0.41553 (14)	0.37788 (9)	0.35848 (8)	0.0176 (2)
C14	0.29433 (13)	0.32995 (9)	0.34973 (8)	0.0168 (2)
H14	0.2069	0.3549	0.3696	0.020*
C15	0.30574 (13)	0.24571 (9)	0.31143 (7)	0.0159 (2)
H15	0.2242	0.2151	0.3059	0.019*
C16	0.28786 (14)	0.19626 (9)	0.11362 (8)	0.0180 (2)
H16	0.3750	0.2209	0.1035	0.022*
C17	0.17711 (14)	0.23325 (9)	0.07308 (8)	0.0190 (2)
H17	0.1910	0.2803	0.0357	0.023*
C18	0.04303 (13)	0.19955 (10)	0.08841 (8)	0.0179 (2)
C19	0.03170 (14)	0.12759 (10)	0.14505 (7)	0.0180 (2)
H19	−0.0549	0.1034	0.1581	0.022*
C20	0.14907 (14)	0.09318 (9)	0.18106 (7)	0.0175 (2)
H20	0.1395	0.0442	0.2171	0.021*
Cu2	0.926147 (17)	0.588239 (11)	0.265503 (9)	0.01796 (4)
N9	1.07098 (11)	0.53919 (8)	0.18340 (6)	0.01519 (19)
N10	1.36478 (12)	0.42921 (8)	0.01531 (6)	0.0183 (2)
H10A	1.4401	0.3975	0.0283	0.022*
H10B	1.3490	0.4372	−0.0324	0.022*
N11	0.91724 (11)	0.45781 (8)	0.31403 (6)	0.01547 (19)
N12	0.91541 (14)	0.18712 (8)	0.41402 (7)	0.0248 (3)
H12A	0.9061	0.1801	0.4631	0.030*
H12B	0.9251	0.1382	0.3855	0.030*
N13	0.77568 (12)	0.64322 (8)	0.34276 (6)	0.0170 (2)
N14	0.45970 (14)	0.77011 (10)	0.49076 (7)	0.0262 (3)
H14A	0.4812	0.8030	0.5284	0.031*
H14B	0.3728	0.7633	0.4835	0.031*
N15	0.91270 (11)	0.71282 (8)	0.20637 (6)	0.01664 (19)
N16	0.89456 (13)	0.95381 (8)	0.06323 (7)	0.0204 (2)
H16A	0.8173	0.9718	0.0428	0.024*
H16B	0.9680	0.9850	0.0537	0.024*
C21	1.05091 (13)	0.55075 (9)	0.10788 (7)	0.0157 (2)
H21	0.9680	0.5832	0.0939	0.019*
C22	1.14589 (13)	0.51732 (9)	0.05055 (7)	0.0156 (2)
H22	1.1273	0.5283	−0.0006	0.019*
C23	1.27166 (12)	0.46630 (9)	0.06954 (7)	0.0141 (2)
C24	1.29340 (13)	0.45489 (9)	0.14834 (7)	0.0164 (2)
H24	1.3753	0.4228	0.1642	0.020*
C25	1.19284 (14)	0.49147 (9)	0.20156 (7)	0.0167 (2)
H25	1.2094	0.4830	0.2532	0.020*
C26	0.92843 (13)	0.37962 (9)	0.27115 (7)	0.0165 (2)
H26	0.9361	0.3873	0.2180	0.020*
C27	0.92913 (14)	0.28925 (9)	0.30160 (7)	0.0171 (2)
H27	0.9389	0.2377	0.2693	0.021*
C28	0.91497 (13)	0.27475 (9)	0.38181 (7)	0.0164 (2)
C29	0.89945 (13)	0.35662 (9)	0.42649 (7)	0.0164 (2)
H29	0.8873	0.3515	0.4797	0.020*
C30	0.90246 (13)	0.44415 (9)	0.39074 (7)	0.0164 (2)
H30	0.8938	0.4973	0.4214	0.020*
C31	0.63836 (14)	0.63335 (10)	0.33431 (8)	0.0185 (2)
H31	0.6150	0.5965	0.2944	0.022*
C32	0.53041 (14)	0.67467 (10)	0.38134 (7)	0.0182 (2)
H32	0.4372	0.6666	0.3723	0.022*
C33	0.56243 (14)	0.72915 (9)	0.44304 (7)	0.0177 (2)
C34	0.70551 (15)	0.73799 (10)	0.45233 (8)	0.0210 (2)
H34	0.7323	0.7723	0.4929	0.025*
C35	0.80628 (14)	0.69599 (10)	0.40169 (8)	0.0196 (2)
H35	0.9004	0.7044	0.4084	0.024*
C36	0.79327 (13)	0.74421 (9)	0.17431 (8)	0.0180 (2)
H36	0.7138	0.7105	0.1845	0.022*
C37	0.78247 (13)	0.82367 (9)	0.12713 (8)	0.0174 (2)
H37	0.6975	0.8426	0.1063	0.021*
C38	0.90066 (13)	0.87553 (9)	0.11090 (7)	0.0160 (2)
C39	1.02509 (14)	0.84304 (9)	0.14474 (8)	0.0181 (2)
H39	1.1061	0.8755	0.1359	0.022*
C40	1.02618 (13)	0.76286 (9)	0.19099 (8)	0.0179 (2)
H40	1.1096	0.7422	0.2127	0.021*
Cl1	0.20362 (3)	0.01980 (2)	0.361362 (18)	0.01910 (6)
Cl2	0.64240 (3)	0.12291 (2)	0.122477 (17)	0.01617 (5)
Cl3	0.69715 (4)	0.51337 (2)	0.161801 (18)	0.02111 (6)
Cl4	1.14798 (3)	0.62545 (2)	0.353735 (19)	0.01962 (6)
O1W	0.82107 (13)	0.18216 (8)	0.57474 (6)	0.0285 (2)
O2W	1.62468 (11)	0.33858 (7)	0.07154 (6)	0.02102 (19)
H1W1	0.810 (2)	0.1333 (8)	0.6007 (10)	0.037 (6)*
H2W1	0.834 (2)	0.2276 (9)	0.6020 (10)	0.039 (6)*
H1W2	1.628 (3)	0.2884 (9)	0.0979 (11)	0.052 (7)*
H2W2	1.648 (2)	0.3826 (10)	0.0992 (11)	0.048 (7)*

	U11	U22	U33	U12	U13	U23
Cu1	0.01684 (7)	0.01299 (7)	0.01708 (7)	0.00168 (5)	−0.00697 (5)	−0.00320 (5)
N1	0.0164 (5)	0.0146 (5)	0.0136 (4)	0.0001 (4)	−0.0033 (3)	−0.0015 (3)
N2	0.0330 (6)	0.0165 (5)	0.0193 (5)	−0.0048 (5)	−0.0016 (5)	−0.0046 (4)
N3	0.0160 (4)	0.0138 (4)	0.0141 (4)	0.0008 (4)	−0.0033 (3)	−0.0021 (3)
N4	0.0158 (5)	0.0302 (6)	0.0149 (5)	0.0041 (4)	−0.0036 (4)	−0.0019 (4)
N5	0.0137 (4)	0.0139 (5)	0.0170 (5)	0.0003 (4)	−0.0035 (3)	−0.0029 (3)
N6	0.0220 (6)	0.0183 (6)	0.0442 (8)	−0.0008 (5)	−0.0034 (5)	−0.0124 (5)
N7	0.0162 (5)	0.0144 (5)	0.0177 (5)	−0.0003 (4)	−0.0053 (4)	−0.0017 (3)
N8	0.0167 (5)	0.0331 (7)	0.0325 (7)	0.0028 (5)	−0.0063 (5)	0.0052 (5)
C1	0.0161 (5)	0.0158 (5)	0.0147 (5)	−0.0011 (4)	−0.0026 (4)	−0.0002 (4)
C2	0.0153 (5)	0.0182 (5)	0.0128 (5)	−0.0008 (4)	−0.0019 (4)	−0.0026 (4)
C3	0.0152 (5)	0.0155 (5)	0.0174 (5)	−0.0013 (4)	−0.0004 (4)	−0.0027 (4)
C4	0.0210 (6)	0.0149 (5)	0.0156 (5)	−0.0019 (4)	−0.0006 (4)	0.0003 (4)
C5	0.0178 (5)	0.0168 (5)	0.0140 (5)	−0.0011 (4)	−0.0024 (4)	−0.0006 (4)
C6	0.0202 (6)	0.0185 (6)	0.0126 (5)	0.0040 (4)	−0.0020 (4)	−0.0032 (4)
C7	0.0173 (5)	0.0215 (6)	0.0146 (5)	0.0044 (5)	−0.0013 (4)	−0.0035 (4)
C8	0.0145 (5)	0.0150 (5)	0.0139 (5)	−0.0009 (4)	−0.0027 (4)	−0.0010 (4)
C9	0.0151 (5)	0.0194 (6)	0.0129 (5)	−0.0009 (4)	−0.0004 (4)	−0.0016 (4)
C10	0.0142 (5)	0.0170 (5)	0.0164 (5)	0.0001 (4)	−0.0014 (4)	−0.0017 (4)
C11	0.0137 (5)	0.0180 (6)	0.0208 (6)	0.0003 (4)	−0.0023 (4)	−0.0026 (4)
C12	0.0149 (5)	0.0165 (6)	0.0262 (6)	−0.0019 (4)	−0.0033 (4)	−0.0036 (4)
C13	0.0188 (5)	0.0138 (5)	0.0202 (6)	0.0003 (4)	−0.0030 (4)	−0.0021 (4)
C14	0.0146 (5)	0.0153 (5)	0.0203 (6)	0.0006 (4)	−0.0007 (4)	−0.0012 (4)
C15	0.0140 (5)	0.0150 (5)	0.0191 (6)	−0.0007 (4)	−0.0032 (4)	−0.0013 (4)
C16	0.0153 (5)	0.0155 (5)	0.0238 (6)	−0.0032 (4)	−0.0044 (4)	0.0006 (4)
C17	0.0177 (5)	0.0158 (6)	0.0239 (6)	−0.0009 (4)	−0.0051 (5)	0.0024 (4)
C18	0.0144 (5)	0.0191 (6)	0.0201 (6)	0.0029 (4)	−0.0045 (4)	−0.0034 (4)
C19	0.0156 (5)	0.0224 (6)	0.0163 (6)	−0.0037 (4)	−0.0010 (4)	−0.0027 (4)
C20	0.0193 (6)	0.0189 (6)	0.0149 (5)	−0.0032 (4)	−0.0023 (4)	−0.0010 (4)
Cu2	0.01974 (8)	0.01387 (7)	0.01829 (8)	0.00360 (6)	0.00663 (6)	0.00303 (5)
N9	0.0154 (4)	0.0139 (4)	0.0155 (5)	0.0015 (4)	0.0009 (3)	0.0007 (3)
N10	0.0168 (5)	0.0225 (5)	0.0146 (5)	0.0031 (4)	0.0012 (4)	−0.0009 (4)
N11	0.0175 (5)	0.0137 (4)	0.0149 (5)	−0.0004 (4)	0.0000 (4)	0.0007 (3)
N12	0.0378 (7)	0.0138 (5)	0.0215 (6)	0.0015 (5)	0.0031 (5)	0.0021 (4)
N13	0.0177 (5)	0.0149 (5)	0.0174 (5)	0.0012 (4)	0.0034 (4)	0.0004 (4)
N14	0.0234 (6)	0.0300 (7)	0.0239 (6)	0.0050 (5)	0.0040 (5)	−0.0088 (5)
N15	0.0157 (5)	0.0145 (5)	0.0186 (5)	0.0015 (4)	0.0030 (4)	0.0015 (4)
N16	0.0218 (5)	0.0163 (5)	0.0226 (6)	−0.0012 (4)	0.0002 (4)	0.0039 (4)
C21	0.0144 (5)	0.0153 (5)	0.0172 (5)	0.0003 (4)	−0.0006 (4)	0.0002 (4)
C22	0.0155 (5)	0.0172 (5)	0.0144 (5)	−0.0011 (4)	−0.0020 (4)	−0.0008 (4)
C23	0.0137 (5)	0.0129 (5)	0.0156 (5)	−0.0017 (4)	0.0002 (4)	−0.0013 (4)
C24	0.0161 (5)	0.0157 (5)	0.0169 (5)	0.0027 (4)	−0.0018 (4)	−0.0002 (4)
C25	0.0192 (5)	0.0156 (5)	0.0147 (5)	0.0021 (4)	0.0000 (4)	0.0006 (4)
C26	0.0176 (5)	0.0172 (5)	0.0144 (5)	−0.0005 (4)	0.0001 (4)	−0.0015 (4)
C27	0.0185 (5)	0.0143 (5)	0.0184 (6)	−0.0003 (4)	0.0003 (4)	−0.0030 (4)
C28	0.0153 (5)	0.0150 (5)	0.0186 (6)	−0.0003 (4)	−0.0005 (4)	0.0009 (4)
C29	0.0185 (5)	0.0159 (5)	0.0143 (5)	0.0004 (4)	0.0000 (4)	0.0005 (4)
C30	0.0189 (5)	0.0148 (5)	0.0153 (5)	0.0002 (4)	−0.0003 (4)	−0.0013 (4)
C31	0.0201 (6)	0.0193 (6)	0.0156 (6)	−0.0007 (5)	0.0018 (4)	−0.0017 (4)
C32	0.0173 (5)	0.0207 (6)	0.0159 (6)	0.0006 (5)	0.0007 (4)	−0.0008 (4)
C33	0.0207 (6)	0.0152 (5)	0.0161 (5)	0.0018 (4)	0.0029 (4)	−0.0001 (4)
C34	0.0226 (6)	0.0208 (6)	0.0199 (6)	−0.0021 (5)	−0.0011 (5)	−0.0051 (5)
C35	0.0180 (6)	0.0182 (6)	0.0226 (6)	−0.0016 (5)	0.0003 (5)	−0.0008 (4)
C36	0.0145 (5)	0.0154 (5)	0.0237 (6)	−0.0011 (4)	0.0011 (4)	0.0000 (4)
C37	0.0146 (5)	0.0154 (5)	0.0219 (6)	0.0000 (4)	−0.0011 (4)	0.0011 (4)
C38	0.0179 (5)	0.0138 (5)	0.0156 (5)	0.0003 (4)	0.0017 (4)	−0.0004 (4)
C39	0.0160 (5)	0.0172 (6)	0.0210 (6)	−0.0026 (4)	0.0010 (4)	0.0003 (4)
C40	0.0143 (5)	0.0174 (6)	0.0215 (6)	0.0008 (4)	0.0000 (4)	0.0006 (4)
Cl1	0.02220 (14)	0.01924 (14)	0.01585 (13)	−0.00149 (11)	−0.00145 (10)	0.00041 (10)
Cl2	0.01525 (12)	0.01728 (13)	0.01575 (13)	−0.00059 (10)	−0.00079 (9)	0.00145 (9)
Cl3	0.02782 (16)	0.02046 (14)	0.01555 (13)	−0.00381 (12)	−0.00212 (11)	−0.00224 (10)
Cl4	0.01772 (13)	0.02048 (14)	0.02104 (14)	−0.00009 (11)	−0.00386 (10)	−0.00442 (11)
O1W	0.0419 (6)	0.0194 (5)	0.0242 (5)	−0.0066 (5)	0.0045 (5)	−0.0017 (4)
O2W	0.0255 (5)	0.0154 (4)	0.0226 (5)	0.0002 (4)	−0.0064 (4)	−0.0015 (4)

Cu1—N1	2.0140 (11)	Cu2—N9	2.0224 (10)
Cu1—N3	2.0177 (10)	Cu2—N13	2.0286 (11)
Cu1—N5	2.0190 (11)	Cu2—Cl4	2.7907 (4)
Cu1—N7	2.0258 (11)	Cu2—Cl3	3.1884 (4)
Cu1—Cl2	2.7199 (3)	N9—C21	1.3498 (16)
Cu1—Cl1	3.2185 (4)	N9—C25	1.3539 (16)
N1—C5	1.3494 (16)	N10—C23	1.3435 (16)
N1—C1	1.3536 (16)	N10—H10A	0.86
N2—C3	1.3431 (17)	N10—H10B	0.86
N2—H2A	0.86	N11—C26	1.3469 (17)
N2—H2B	0.86	N11—C30	1.3478 (16)
N3—C10	1.3466 (16)	N12—C28	1.3485 (17)
N3—C6	1.3506 (16)	N12—H12A	0.86
N4—C8	1.3431 (16)	N12—H12B	0.86
N4—H4A	0.86	N13—C31	1.3465 (18)
N4—H4B	0.86	N13—C35	1.3482 (18)
N5—C11	1.3468 (17)	N14—C33	1.3502 (17)
N5—C15	1.3496 (16)	N14—H14A	0.86
N6—C13	1.3564 (18)	N14—H14B	0.86
N6—H6A	0.86	N15—C36	1.3451 (17)
N6—H6B	0.86	N15—C40	1.3453 (17)
N7—C16	1.3466 (17)	N16—C38	1.3685 (17)
N7—C20	1.3477 (17)	N16—H16A	0.86
N8—C18	1.3455 (17)	N16—H16B	0.86
N8—H8A	0.86	C21—C22	1.3735 (17)
N8—H8B	0.86	C21—H21	0.93
C1—C2	1.3716 (18)	C22—C23	1.4095 (17)
C1—H1	0.93	C22—H22	0.93
C2—C3	1.4073 (18)	C23—C24	1.4092 (18)
C2—H2	0.93	C24—C25	1.3726 (17)
C3—C4	1.4104 (18)	C24—H24	0.93
C4—C5	1.3757 (18)	C25—H25	0.93
C4—H4	0.93	C26—C27	1.3723 (18)
C5—H5	0.93	C26—H26	0.93
C6—C7	1.3695 (18)	C27—C28	1.4091 (18)
C6—H6	0.93	C27—H27	0.93
C7—C8	1.4080 (17)	C28—C29	1.4080 (18)
C7—H7	0.93	C29—C30	1.3742 (18)
C8—C9	1.4098 (17)	C29—H29	0.93
C9—C10	1.3765 (18)	C30—H30	0.93
C9—H9	0.93	C31—C32	1.3783 (18)
C10—H10	0.93	C31—H31	0.93
C11—C12	1.3721 (19)	C32—C33	1.4050 (19)
C11—H11	0.93	C32—H32	0.93
C12—C13	1.4071 (18)	C33—C34	1.401 (2)
C12—H12	0.93	C34—C35	1.3742 (19)
C13—C14	1.4025 (18)	C34—H34	0.93
C14—C15	1.3770 (18)	C35—H35	0.93
C14—H14	0.93	C36—C37	1.3786 (18)
C15—H15	0.93	C36—H36	0.93
C16—C17	1.3762 (18)	C37—C38	1.3996 (18)
C16—H16	0.93	C37—H37	0.93
C17—C18	1.4044 (19)	C38—C39	1.4043 (19)
C17—H17	0.93	C39—C40	1.3755 (18)
C18—C19	1.4057 (19)	C39—H39	0.93
C19—C20	1.3738 (19)	C40—H40	0.93
C19—H19	0.93	O1W—H1W1	0.827 (9)
C20—H20	0.93	O1W—H2W1	0.833 (9)
Cu2—N11	2.0165 (11)	O2W—H1W2	0.835 (9)
Cu2—N15	2.0206 (11)	O2W—H2W2	0.849 (9)
N1—Cu1—N3	91.10 (4)	N11—Cu2—N9	91.26 (4)
N1—Cu1—N5	173.52 (4)	N15—Cu2—N9	88.17 (4)
N3—Cu1—N5	89.52 (4)	N11—Cu2—N13	91.71 (4)
N1—Cu1—N7	89.32 (4)	N15—Cu2—N13	88.57 (4)
N3—Cu1—N7	173.70 (4)	N9—Cu2—N13	176.35 (4)
N5—Cu1—N7	89.35 (4)	N11—Cu2—Cl4	90.90 (3)
N1—Cu1—Cl2	92.32 (3)	N15—Cu2—Cl4	97.84 (3)
N3—Cu1—Cl2	91.83 (3)	N9—Cu2—Cl4	88.13 (3)
N5—Cu1—Cl2	94.11 (3)	N13—Cu2—Cl4	93.94 (3)
N7—Cu1—Cl2	94.43 (3)	N11—Cu2—Cl3	82.30 (3)
N1—Cu1—Cl1	86.84 (3)	N15—Cu2—Cl3	88.92 (3)
N3—Cu1—Cl1	86.48 (3)	N9—Cu2—Cl3	86.13 (3)
N5—Cu1—Cl1	86.76 (3)	N13—Cu2—Cl3	92.17 (3)
N7—Cu1—Cl1	87.27 (3)	Cl4—Cu2—Cl3	170.991 (11)
Cl2—Cu1—Cl1	178.098 (10)	C21—N9—C25	116.39 (11)
C5—N1—C1	116.35 (11)	C21—N9—Cu2	122.13 (8)
C5—N1—Cu1	122.70 (9)	C25—N9—Cu2	121.47 (9)
C1—N1—Cu1	120.80 (9)	C23—N10—H10A	120.0
C3—N2—H2A	120.0	C23—N10—H10B	120.0
C3—N2—H2B	120.0	H10A—N10—H10B	120.0
H2A—N2—H2B	120.0	C26—N11—C30	116.62 (11)
C10—N3—C6	116.61 (11)	C26—N11—Cu2	121.42 (9)
C10—N3—Cu1	120.95 (8)	C30—N11—Cu2	121.96 (9)
C6—N3—Cu1	122.37 (9)	C28—N12—H12A	120.0
C8—N4—H4A	120.0	C28—N12—H12B	120.0
C8—N4—H4B	120.0	H12A—N12—H12B	120.0
H4A—N4—H4B	120.0	C31—N13—C35	116.72 (11)
C11—N5—C15	116.96 (11)	C31—N13—Cu2	120.80 (9)
C11—N5—Cu1	122.09 (8)	C35—N13—Cu2	122.35 (9)
C15—N5—Cu1	120.91 (9)	C33—N14—H14A	120.0
C13—N6—H6A	120.0	C33—N14—H14B	120.0
C13—N6—H6B	120.0	H14A—N14—H14B	120.0
H6A—N6—H6B	120.0	C36—N15—C40	117.21 (11)
C16—N7—C20	116.54 (11)	C36—N15—Cu2	121.08 (9)
C16—N7—Cu1	123.33 (9)	C40—N15—Cu2	121.39 (9)
C20—N7—Cu1	119.96 (9)	C38—N16—H16A	120.0
C18—N8—H8A	120.0	C38—N16—H16B	120.0
C18—N8—H8B	120.0	H16A—N16—H16B	120.0
H8A—N8—H8B	120.0	N9—C21—C22	123.79 (11)
N1—C1—C2	124.04 (12)	N9—C21—H21	118.1
N1—C1—H1	118.0	C22—C21—H21	118.1
C2—C1—H1	118.0	C21—C22—C23	119.77 (11)
C1—C2—C3	119.61 (11)	C21—C22—H22	120.1
C1—C2—H2	120.2	C23—C22—H22	120.1
C3—C2—H2	120.2	N10—C23—C24	121.81 (11)
N2—C3—C2	121.70 (12)	N10—C23—C22	121.67 (11)
N2—C3—C4	121.76 (12)	C24—C23—C22	116.51 (11)
C2—C3—C4	116.53 (11)	C25—C24—C23	119.55 (11)
C5—C4—C3	119.69 (12)	C25—C24—H24	120.2
C5—C4—H4	120.2	C23—C24—H24	120.2
C3—C4—H4	120.2	N9—C25—C24	123.97 (12)
N1—C5—C4	123.77 (12)	N9—C25—H25	118.0
N1—C5—H5	118.1	C24—C25—H25	118.0
C4—C5—H5	118.1	N11—C26—C27	123.57 (12)
N3—C6—C7	123.97 (12)	N11—C26—H26	118.2
N3—C6—H6	118.0	C27—C26—H26	118.2
C7—C6—H6	118.0	C26—C27—C28	119.91 (12)
C6—C7—C8	119.66 (12)	C26—C27—H27	120.0
C6—C7—H7	120.2	C28—C27—H27	120.0
C8—C7—H7	120.2	N12—C28—C29	121.79 (12)
N4—C8—C7	122.44 (11)	N12—C28—C27	121.76 (12)
N4—C8—C9	121.15 (11)	C29—C28—C27	116.45 (11)
C7—C8—C9	116.41 (11)	C30—C29—C28	119.36 (12)
C10—C9—C8	119.74 (11)	C30—C29—H29	120.3
C10—C9—H9	120.1	C28—C29—H29	120.3
C8—C9—H9	120.1	N11—C30—C29	124.06 (12)
N3—C10—C9	123.60 (11)	N11—C30—H30	118.0
N3—C10—H10	118.2	C29—C30—H30	118.0
C9—C10—H10	118.2	N13—C31—C32	123.80 (13)
N5—C11—C12	123.69 (12)	N13—C31—H31	118.1
N5—C11—H11	118.2	C32—C31—H31	118.1
C12—C11—H11	118.2	C31—C32—C33	119.43 (13)
C11—C12—C13	119.42 (12)	C31—C32—H32	120.3
C11—C12—H12	120.3	C33—C32—H32	120.3
C13—C12—H12	120.3	N14—C33—C34	122.24 (13)
N6—C13—C14	121.09 (12)	N14—C33—C32	121.20 (13)
N6—C13—C12	121.88 (12)	C34—C33—C32	116.56 (12)
C14—C13—C12	117.02 (12)	C35—C34—C33	120.14 (13)
C15—C14—C13	119.50 (11)	C35—C34—H34	119.9
C15—C14—H14	120.2	C33—C34—H34	119.9
C13—C14—H14	120.2	N13—C35—C34	123.33 (13)
N5—C15—C14	123.41 (12)	N13—C35—H35	118.3
N5—C15—H15	118.3	C34—C35—H35	118.3
C14—C15—H15	118.3	N15—C36—C37	123.47 (12)
N7—C16—C17	123.80 (12)	N15—C36—H36	118.3
N7—C16—H16	118.1	C37—C36—H36	118.3
C17—C16—H16	118.1	C36—C37—C38	119.33 (12)
C16—C17—C18	119.65 (12)	C36—C37—H37	120.3
C16—C17—H17	120.2	C38—C37—H37	120.3
C18—C17—H17	120.2	N16—C38—C37	120.96 (12)
N8—C18—C17	122.71 (13)	N16—C38—C39	121.87 (12)
N8—C18—C19	120.80 (13)	C37—C38—C39	117.17 (11)
C17—C18—C19	116.49 (12)	C40—C39—C38	119.49 (12)
C20—C19—C18	119.76 (12)	C40—C39—H39	120.3
C20—C19—H19	120.1	C38—C39—H39	120.3
C18—C19—H19	120.1	N15—C40—C39	123.33 (12)
N7—C20—C19	123.73 (12)	N15—C40—H40	118.3
N7—C20—H20	118.1	C39—C40—H40	118.3
C19—C20—H20	118.1	H1W1—O1W—H2W1	111.7 (14)
N11—Cu2—N15	171.22 (5)	H1W2—O2W—H2W2	107.8 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl2i	0.93	2.68	3.5955 (13)	167
C6—H6···Cl2	0.93	2.80	3.3665 (13)	121
C10—H10···Cl1	0.93	2.78	3.4430 (13)	129
C20—H20···Cl1	0.93	2.64	3.3522 (13)	134
C25—H25···Cl4	0.93	2.71	3.2928 (13)	121
C26—H26···N9	0.93	2.62	3.0473 (17)	108
C35—H35···Cl4	0.93	2.67	3.3947 (14)	136
N4—H4A···O1Wii	0.86	2.38	3.2094 (17)	163
N4—H4B···Cl1iii	0.86	2.43	3.2893 (13)	175
N6—H6A···Cl4iv	0.86	2.82	3.4066 (13)	127
N8—H8B···Cl2iv	0.86	2.56	3.4021 (13)	166
N10—H10B···Cl3v	0.86	2.41	3.2596 (11)	171
N12—H12A···O1W	0.86	2.06	2.8908 (16)	162
N14—H14B···O1Wvi	0.86	2.25	3.0103 (18)	147
N16—H16B···N16vii	0.86	2.52	3.2036 (17)	137
O1W—H1W1···Cl1iii	0.83 (1)	2.26 (1)	3.0614 (12)	163 (2)
O1W—H2W1···Cl4viii	0.83 (1)	2.26 (1)	3.0694 (12)	164 (2)
C37—H37···Cg1ix	0.93	2.81	3.5492 (14)	137
C39—H39···Cg1x	0.93	2.95	3.7306 (14)	142
N2—H2B···Cg2xi	0.86	2.75	3.3359 (13)	126
C12—H12···Cg3	0.93	2.79	3.6488 (14)	154
C14—H14···Cg3iv	0.93	2.83	3.6193 (13)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are centroids of the N1/C1–C5, N9/C21–C25 and N11/C26–C30 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cl2i	0.93	2.68	3.5955 (13)	167
C6—H6⋯Cl2	0.93	2.80	3.3665 (13)	121
C10—H10⋯Cl1	0.93	2.78	3.4430 (13)	129
C20—H20⋯Cl1	0.93	2.64	3.3522 (13)	134
C25—H25⋯Cl4	0.93	2.71	3.2928 (13)	121
C26—H26⋯N9	0.93	2.62	3.0473 (17)	108
C35—H35⋯Cl4	0.93	2.67	3.3947 (14)	136
N4—H4A⋯O1Wii	0.86	2.38	3.2094 (17)	163
N4—H4B⋯Cl1iii	0.86	2.43	3.2893 (13)	175
N6—H6A⋯Cl4iv	0.86	2.82	3.4066 (13)	127
N8—H8B⋯Cl2iv	0.86	2.56	3.4021 (13)	166
N10—H10B⋯Cl3v	0.86	2.41	3.2596 (11)	171
N12—H12A⋯O1W	0.86	2.06	2.8908 (16)	162
N14—H14B⋯O1Wvi	0.86	2.25	3.0103 (18)	147
N16—H16B⋯N16vii	0.86	2.52	3.2036 (17)	137
O1W—H1W1⋯Cl1iii	0.83 (1)	2.26 (1)	3.0614 (12)	163 (2)
O1W—H2W1⋯Cl4viii	0.83 (1)	2.26 (1)	3.0694 (12)	164 (2)
C37—H37⋯Cg1ix	0.93	2.81	3.5492 (14)	137
C39—H39⋯Cg1x	0.93	2.95	3.7306 (14)	142
N2—H2B⋯Cg2xi	0.86	2.75	3.3359 (13)	126
C12—H12⋯Cg3	0.93	2.79	3.6488 (14)	154
C14—H14⋯Cg3iv	0.93	2.83	3.6193 (13)	144

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