[μ-N,N,N',N'-Tetra-kis-(2-pyridyl-meth-yl)pentane-1,5-diamine]-bis-[dichlorido-copper(II)] sesquihydrate.

In the title dinuclear copper complex, [Cu(2)Cl(4)(C(29)H(34)N(6))]·1.5H(2)O, both Cu(II) ions are coordinated in a slightly distorted square-pyramidal environment in which the N atoms of the dipicolyl-amine group and a chloride ligand form the basal plane. The apical position is occupied by a second chloride atom. The Cu-N distances involving the pyridine N atoms differ slightly from each other and the Cu-N distance involving the tertiary N atom is the longest. The apical Cu-Cl distance is elongated compared to its basal counterpart due to typical Jahn-Teller distortion. In the crystal structure, complex and water mol-ecules are linked via inter-molecular O-H⋯O and O-H⋯Cl hydrogen bonds into chains along [001]. One of the water mol-ecules was refined with half occupancy.

Related literature

For crystallographic data of tetra­kis­(pyridin-2-yl-meth­yl)alkyl-diamines, see: Fujihara et al. (2004 ▶); Mambanda et al. (2007 ▶). For the superoxide dismutase activity of iron complexes, see: Tamura et al. (2000 ▶). For dinuclear Pt complexes of similar ligands, see: Ertürk et al. (2007 ▶). For the use of the dipicolyl­amine moiety for binding of the M(CO)3 core (M = Re, 99Tc), see: Bartholomä et al. (2009 ▶). For crystal structures closely related to the title compound, see: Bartholomä et al. (2010a ▶,b ▶,c ▶,d ▶).

Experimental

Crystal data

[Cu2Cl4(C29H34N6)]·1.5H2O

M = 762.55

Monoclinic,

a = 8.2003 (13) Å

b = 14.3700 (16) Å

c = 27.688 (4) Å

β = 97.919 (6)°

V = 3231.6 (8) Å3

Z = 4

Mo Kα radiation

μ = 1.68 mm−1

T = 90 K

0.22 × 0.16 × 0.12 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.709, T max = 0.824

31227 measured reflections

7827 independent reflections

7421 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.079

wR(F 2) = 0.156

S = 1.40

7827 reflections

404 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.81 e Å−3

Δρmin = −0.67 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810034513/lh5109sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034513/lh5109Isup2.hkl

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

[Cu2Cl4(C29H34N6)]·1.5H2O	F(000) = 1564
Mr = 762.55	Dx = 1.561 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6480 reflections
a = 8.2003 (13) Å	θ = 5.3–56.1°
b = 14.3700 (16) Å	µ = 1.68 mm−1
c = 27.688 (4) Å	T = 90 K
β = 97.919 (6)°	Neeldes, blue
V = 3231.6 (8) Å3	0.22 × 0.16 × 0.12 mm
Z = 4

Bruker APEX CCD diffractometer	7827 independent reflections
Radiation source: fine-focus sealed tube	7421 reflections with I > 2σ(I)
graphite	Rint = 0.050
Detector resolution: 512 pixels mm-1	θmax = 28.1°, θmin = 1.6°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −18→18
Tmin = 0.709, Tmax = 0.824	l = −36→35
31227 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)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.40	w = 1/[σ2(Fo2) + (0.0289P)2 + 16.2006P] where P = (Fo2 + 2Fc2)/3
7827 reflections	(Δ/σ)max = 0.003
404 parameters	Δρmax = 0.81 e Å−3
5 restraints	Δρmin = −0.67 e Å−3

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	Occ. (<1)
Cu1	0.27113 (7)	0.72996 (4)	1.01183 (2)	0.01076 (13)
Cu2	0.27749 (7)	0.33032 (4)	0.71531 (2)	0.01413 (14)
Cl1	0.18034 (14)	0.87113 (8)	1.05552 (4)	0.0141 (2)
Cl2	0.37112 (16)	0.61583 (9)	1.06521 (5)	0.0213 (3)
Cl3	0.41385 (17)	0.36546 (10)	0.65260 (5)	0.0258 (3)
Cl4	0.10401 (16)	0.18600 (9)	0.69447 (5)	0.0215 (3)
O1	0.2269 (9)	0.9799 (4)	0.6606 (2)	0.0570 (16)
O2	0.9605 (10)	0.2886 (6)	0.8770 (3)	0.0253 (17)	0.50
N1	0.4863 (5)	0.7920 (3)	1.00962 (14)	0.0113 (8)
N2	0.2270 (5)	0.7828 (3)	0.94143 (14)	0.0114 (8)
N3	0.0433 (5)	0.6801 (3)	0.99475 (15)	0.0120 (8)
N4	0.4603 (5)	0.2609 (3)	0.75526 (15)	0.0159 (8)
N5	0.2081 (5)	0.3520 (3)	0.78308 (15)	0.0132 (8)
N6	0.0870 (5)	0.4163 (3)	0.69621 (15)	0.0168 (9)
C1	0.3151 (6)	0.8723 (3)	0.94483 (17)	0.0114 (9)
H1A	0.2495	0.9199	0.9594	0.014*
H1B	0.3315	0.8937	0.9118	0.014*
C2	0.4794 (6)	0.8601 (3)	0.97598 (17)	0.0140 (9)
C3	0.6144 (6)	0.9175 (3)	0.97175 (19)	0.0158 (10)
H3	0.6075	0.9657	0.9480	0.019*
C4	0.7587 (6)	0.9022 (4)	1.0032 (2)	0.0190 (11)
H4	0.8526	0.9401	1.0012	0.023*
C5	0.7659 (6)	0.8316 (4)	1.03749 (19)	0.0180 (10)
H5	0.8642	0.8201	1.0591	0.022*
C6	0.6271 (6)	0.7785 (3)	1.03951 (18)	0.0156 (9)
H6	0.6314	0.7302	1.0631	0.019*
C7	0.0454 (6)	0.7921 (3)	0.92979 (17)	0.0131 (9)
H7A	0.0132	0.7887	0.8940	0.016*
H7B	0.0108	0.8535	0.9411	0.016*
C8	−0.0398 (6)	0.7164 (3)	0.95395 (17)	0.0132 (9)
C9	−0.1994 (6)	0.6872 (3)	0.93578 (17)	0.0141 (9)
H9	−0.2557	0.7132	0.9066	0.017*
C10	−0.2733 (6)	0.6204 (3)	0.96078 (19)	0.0169 (10)
H10	−0.3812	0.5992	0.9490	0.020*
C11	−0.1882 (6)	0.5841 (4)	1.0036 (2)	0.0199 (11)
H11	−0.2382	0.5388	1.0218	0.024*
C12	−0.0301 (6)	0.6148 (3)	1.01933 (19)	0.0175 (10)
H12	0.0286	0.5892	1.0483	0.021*
C13	0.2943 (6)	0.7235 (3)	0.90419 (17)	0.0128 (9)
H13A	0.4160	0.7265	0.9103	0.015*
H13B	0.2590	0.7506	0.8716	0.015*
C14	0.2430 (6)	0.6220 (3)	0.90307 (16)	0.0129 (9)
H14A	0.1215	0.6173	0.8992	0.016*
H14B	0.2880	0.5915	0.9341	0.016*
C15	0.3081 (6)	0.5735 (4)	0.86064 (19)	0.0172 (10)
H15A	0.4298	0.5711	0.8673	0.021*
H15B	0.2780	0.6109	0.8307	0.021*
C16	0.2422 (6)	0.4749 (3)	0.85142 (18)	0.0165 (10)
H16A	0.1211	0.4746	0.8504	0.020*
H16B	0.2902	0.4334	0.8782	0.020*
C17	0.2879 (6)	0.4396 (3)	0.80292 (17)	0.0147 (9)
H17A	0.2611	0.4891	0.7783	0.018*
H17B	0.4086	0.4303	0.8069	0.018*
C18	0.2662 (6)	0.2696 (3)	0.81311 (18)	0.0161 (10)
H18A	0.1872	0.2176	0.8061	0.019*
H18B	0.2738	0.2851	0.8482	0.019*
C19	0.4314 (6)	0.2415 (3)	0.80118 (18)	0.0155 (9)
C20	0.5471 (7)	0.1945 (4)	0.8336 (2)	0.0222 (11)
H20	0.5277	0.1838	0.8662	0.027*
C21	0.6906 (7)	0.1636 (4)	0.8181 (2)	0.0268 (12)
H21	0.7702	0.1306	0.8397	0.032*
C22	0.7170 (7)	0.1812 (4)	0.7709 (2)	0.0218 (11)
H22	0.8136	0.1590	0.7593	0.026*
C23	0.6002 (7)	0.2317 (4)	0.74057 (19)	0.0207 (11)
H23	0.6204	0.2460	0.7084	0.025*
C24	0.0260 (6)	0.3601 (4)	0.77349 (19)	0.0181 (10)
H24A	−0.0155	0.3899	0.8017	0.022*
H24B	−0.0239	0.2974	0.7689	0.022*
C25	−0.0214 (6)	0.4176 (4)	0.72845 (19)	0.0192 (10)
C26	−0.1696 (7)	0.4657 (4)	0.7199 (2)	0.0241 (12)
H26	−0.2452	0.4649	0.7430	0.029*
C27	−0.2036 (7)	0.5149 (4)	0.6766 (2)	0.0301 (14)
H27	−0.3053	0.5470	0.6692	0.036*
C28	−0.0899 (8)	0.5172 (4)	0.6444 (2)	0.0274 (13)
H28	−0.1099	0.5527	0.6152	0.033*
C29	0.0536 (7)	0.4668 (4)	0.6552 (2)	0.0225 (11)
H29	0.1318	0.4680	0.6329	0.027*
H1WA	0.208 (14)	1.035 (3)	0.668 (4)	0.10 (4)*
H1WB	0.266 (9)	0.972 (6)	0.6345 (17)	0.05 (2)*
H2WA	0.889 (10)	0.330 (5)	0.871 (5)	0.04 (4)*	0.50
H2WB	0.904 (10)	0.242 (4)	0.882 (4)	0.02 (3)*	0.50

	U11	U22	U33	U12	U13	U23
Cu1	0.0096 (3)	0.0114 (3)	0.0112 (3)	−0.0016 (2)	0.0012 (2)	0.0018 (2)
Cu2	0.0172 (3)	0.0144 (3)	0.0109 (3)	0.0015 (2)	0.0023 (2)	−0.0014 (2)
Cl1	0.0143 (5)	0.0144 (5)	0.0144 (5)	−0.0022 (4)	0.0044 (4)	−0.0035 (4)
Cl2	0.0212 (6)	0.0173 (6)	0.0238 (6)	−0.0021 (5)	−0.0028 (5)	0.0082 (5)
Cl3	0.0299 (7)	0.0301 (7)	0.0190 (6)	0.0026 (6)	0.0094 (5)	0.0040 (5)
Cl4	0.0265 (6)	0.0175 (6)	0.0198 (6)	−0.0050 (5)	0.0003 (5)	−0.0031 (5)
O1	0.085 (4)	0.037 (3)	0.060 (4)	−0.001 (3)	0.052 (3)	−0.002 (3)
O2	0.023 (4)	0.025 (4)	0.028 (4)	−0.002 (3)	0.006 (3)	0.005 (3)
N1	0.0084 (17)	0.0120 (19)	0.0145 (19)	0.0006 (14)	0.0053 (14)	−0.0030 (15)
N2	0.0122 (18)	0.0108 (19)	0.0111 (18)	−0.0029 (15)	0.0020 (14)	−0.0013 (14)
N3	0.0131 (18)	0.0085 (18)	0.0154 (19)	−0.0025 (14)	0.0052 (15)	−0.0003 (15)
N4	0.016 (2)	0.014 (2)	0.018 (2)	−0.0005 (16)	0.0032 (16)	−0.0031 (16)
N5	0.0125 (19)	0.013 (2)	0.0141 (19)	0.0033 (15)	0.0028 (15)	0.0014 (15)
N6	0.019 (2)	0.018 (2)	0.013 (2)	−0.0027 (17)	−0.0012 (16)	−0.0039 (16)
C1	0.014 (2)	0.009 (2)	0.012 (2)	−0.0028 (17)	0.0033 (17)	−0.0009 (16)
C2	0.015 (2)	0.014 (2)	0.014 (2)	−0.0013 (18)	0.0048 (18)	−0.0079 (18)
C3	0.016 (2)	0.011 (2)	0.023 (3)	−0.0052 (18)	0.0107 (19)	−0.0044 (19)
C4	0.014 (2)	0.016 (2)	0.029 (3)	−0.0032 (19)	0.009 (2)	−0.015 (2)
C5	0.008 (2)	0.025 (3)	0.021 (2)	0.0015 (19)	0.0016 (18)	−0.011 (2)
C6	0.016 (2)	0.015 (2)	0.016 (2)	0.0001 (18)	0.0032 (18)	−0.0042 (18)
C7	0.012 (2)	0.014 (2)	0.013 (2)	0.0003 (17)	0.0014 (17)	−0.0003 (17)
C8	0.017 (2)	0.009 (2)	0.015 (2)	0.0028 (17)	0.0069 (18)	−0.0032 (17)
C9	0.013 (2)	0.016 (2)	0.013 (2)	0.0010 (18)	0.0013 (17)	−0.0034 (18)
C10	0.015 (2)	0.014 (2)	0.022 (3)	0.0006 (18)	0.0024 (19)	−0.0023 (19)
C11	0.017 (2)	0.014 (2)	0.031 (3)	−0.0026 (19)	0.011 (2)	0.004 (2)
C12	0.020 (2)	0.014 (2)	0.019 (2)	0.0021 (19)	0.0026 (19)	0.0045 (19)
C13	0.013 (2)	0.013 (2)	0.013 (2)	−0.0025 (17)	0.0019 (17)	−0.0034 (17)
C14	0.018 (2)	0.014 (2)	0.008 (2)	−0.0015 (18)	0.0043 (17)	−0.0011 (17)
C15	0.019 (2)	0.016 (2)	0.018 (2)	−0.0020 (19)	0.0085 (19)	−0.0039 (19)
C16	0.023 (3)	0.014 (2)	0.013 (2)	−0.0006 (19)	0.0070 (19)	−0.0024 (18)
C17	0.017 (2)	0.015 (2)	0.011 (2)	−0.0003 (18)	0.0002 (18)	−0.0008 (18)
C18	0.024 (2)	0.011 (2)	0.014 (2)	0.0023 (19)	0.0052 (19)	0.0036 (18)
C19	0.022 (2)	0.010 (2)	0.015 (2)	0.0001 (18)	0.0014 (19)	−0.0010 (18)
C20	0.030 (3)	0.019 (3)	0.017 (2)	0.003 (2)	0.000 (2)	0.001 (2)
C21	0.026 (3)	0.025 (3)	0.027 (3)	0.008 (2)	−0.004 (2)	0.001 (2)
C22	0.018 (2)	0.019 (3)	0.028 (3)	0.001 (2)	0.003 (2)	−0.009 (2)
C23	0.024 (3)	0.021 (3)	0.018 (2)	−0.004 (2)	0.007 (2)	−0.008 (2)
C24	0.015 (2)	0.018 (2)	0.021 (3)	0.0002 (19)	0.0017 (19)	−0.002 (2)
C25	0.020 (2)	0.014 (2)	0.022 (3)	−0.001 (2)	−0.002 (2)	−0.003 (2)
C26	0.018 (3)	0.017 (3)	0.036 (3)	0.002 (2)	−0.001 (2)	−0.004 (2)
C27	0.028 (3)	0.016 (3)	0.044 (4)	0.009 (2)	−0.006 (3)	−0.005 (2)
C28	0.038 (3)	0.015 (3)	0.025 (3)	0.000 (2)	−0.007 (2)	0.000 (2)
C29	0.030 (3)	0.016 (2)	0.020 (3)	−0.005 (2)	−0.001 (2)	−0.003 (2)

Cu1—N1	1.986 (4)	C9—C10	1.372 (7)
Cu1—N3	1.996 (4)	C9—H9	0.9500
Cu1—N2	2.076 (4)	C10—C11	1.392 (7)
Cu1—Cl2	2.2832 (13)	C10—H10	0.9500
Cu1—Cl1	2.5261 (13)	C11—C12	1.382 (7)
Cu2—N4	2.002 (4)	C11—H11	0.9500
Cu2—N6	2.005 (4)	C12—H12	0.9500
Cu2—N5	2.058 (4)	C13—C14	1.517 (6)
Cu2—Cl3	2.2484 (14)	C13—H13A	0.9900
Cu2—Cl4	2.5361 (14)	C13—H13B	0.9900
O1—H1WA	0.84 (2)	C14—C15	1.524 (6)
O1—H1WB	0.84 (2)	C14—H14A	0.9900
O2—H2WA	0.84 (2)	C14—H14B	0.9900
O2—H2WB	0.83 (2)	C15—C16	1.525 (7)
N1—C6	1.339 (6)	C15—H15A	0.9900
N1—C2	1.346 (6)	C15—H15B	0.9900
N2—C1	1.473 (6)	C16—C17	1.529 (7)
N2—C7	1.486 (6)	C16—H16A	0.9900
N2—C13	1.500 (6)	C16—H16B	0.9900
N3—C8	1.342 (6)	C17—H17A	0.9900
N3—C12	1.348 (6)	C17—H17B	0.9900
N4—C23	1.337 (7)	C18—C19	1.494 (7)
N4—C19	1.354 (6)	C18—H18A	0.9900
N5—C24	1.485 (6)	C18—H18B	0.9900
N5—C17	1.487 (6)	C19—C20	1.388 (7)
N5—C18	1.488 (6)	C20—C21	1.381 (8)
N6—C29	1.343 (7)	C20—H20	0.9500
N6—C25	1.344 (7)	C21—C22	1.376 (8)
C1—C2	1.507 (6)	C21—H21	0.9500
C1—H1A	0.9900	C22—C23	1.389 (8)
C1—H1B	0.9900	C22—H22	0.9500
C2—C3	1.399 (7)	C23—H23	0.9500
C3—C4	1.386 (7)	C24—C25	1.502 (7)
C3—H3	0.9500	C24—H24A	0.9900
C4—C5	1.386 (8)	C24—H24B	0.9900
C4—H4	0.9500	C25—C26	1.390 (7)
C5—C6	1.378 (7)	C26—C27	1.387 (9)
C5—H5	0.9500	C26—H26	0.9500
C6—H6	0.9500	C27—C28	1.377 (9)
C7—C8	1.499 (7)	C27—H27	0.9500
C7—H7A	0.9900	C28—C29	1.379 (8)
C7—H7B	0.9900	C28—H28	0.9500
C8—C9	1.400 (7)	C29—H29	0.9500
N1—Cu1—N3	163.88 (16)	C9—C10—H10	120.4
N1—Cu1—N2	81.22 (16)	C11—C10—H10	120.4
N3—Cu1—N2	82.68 (16)	C12—C11—C10	119.1 (5)
N1—Cu1—Cl2	95.81 (12)	C12—C11—H11	120.4
N3—Cu1—Cl2	97.84 (12)	C10—C11—H11	120.4
N2—Cu1—Cl2	150.55 (12)	N3—C12—C11	121.9 (5)
N1—Cu1—Cl1	88.61 (11)	N3—C12—H12	119.1
N3—Cu1—Cl1	94.23 (12)	C11—C12—H12	119.1
N2—Cu1—Cl1	97.55 (11)	N2—C13—C14	115.7 (4)
Cl2—Cu1—Cl1	111.72 (5)	N2—C13—H13A	108.4
N4—Cu2—N6	161.75 (17)	C14—C13—H13A	108.4
N4—Cu2—N5	81.47 (16)	N2—C13—H13B	108.4
N6—Cu2—N5	81.02 (16)	C14—C13—H13B	108.4
N4—Cu2—Cl3	97.15 (13)	H13A—C13—H13B	107.4
N6—Cu2—Cl3	96.33 (13)	C13—C14—C15	109.3 (4)
N5—Cu2—Cl3	154.07 (13)	C13—C14—H14A	109.8
N4—Cu2—Cl4	94.14 (13)	C15—C14—H14A	109.8
N6—Cu2—Cl4	92.95 (13)	C13—C14—H14B	109.8
N5—Cu2—Cl4	96.58 (12)	C15—C14—H14B	109.8
Cl3—Cu2—Cl4	109.33 (5)	H14A—C14—H14B	108.3
H1WA—O1—H1WB	117 (9)	C14—C15—C16	113.6 (4)
H2WA—O2—H2WB	102 (3)	C14—C15—H15A	108.8
C6—N1—C2	118.9 (4)	C16—C15—H15A	108.8
C6—N1—Cu1	127.6 (3)	C14—C15—H15B	108.8
C2—N1—Cu1	113.3 (3)	C16—C15—H15B	108.8
C1—N2—C7	113.8 (4)	H15A—C15—H15B	107.7
C1—N2—C13	108.5 (4)	C15—C16—C17	109.4 (4)
C7—N2—C13	110.8 (3)	C15—C16—H16A	109.8
C1—N2—Cu1	103.8 (3)	C17—C16—H16A	109.8
C7—N2—Cu1	106.0 (3)	C15—C16—H16B	109.8
C13—N2—Cu1	113.9 (3)	C17—C16—H16B	109.8
C8—N3—C12	119.0 (4)	H16A—C16—H16B	108.2
C8—N3—Cu1	114.2 (3)	N5—C17—C16	117.2 (4)
C12—N3—Cu1	126.8 (3)	N5—C17—H17A	108.0
C23—N4—C19	119.3 (4)	C16—C17—H17A	108.0
C23—N4—Cu2	126.7 (4)	N5—C17—H17B	108.0
C19—N4—Cu2	114.0 (3)	C16—C17—H17B	108.0
C24—N5—C17	112.4 (4)	H17A—C17—H17B	107.2
C24—N5—C18	113.5 (4)	N5—C18—C19	108.8 (4)
C17—N5—C18	112.1 (4)	N5—C18—H18A	109.9
C24—N5—Cu2	104.3 (3)	C19—C18—H18A	109.9
C17—N5—Cu2	107.6 (3)	N5—C18—H18B	109.9
C18—N5—Cu2	106.4 (3)	C19—C18—H18B	109.9
C29—N6—C25	118.5 (5)	H18A—C18—H18B	108.3
C29—N6—Cu2	128.1 (4)	N4—C19—C20	121.0 (5)
C25—N6—Cu2	113.3 (3)	N4—C19—C18	115.7 (4)
N2—C1—C2	109.1 (4)	C20—C19—C18	123.2 (5)
N2—C1—H1A	109.9	C21—C20—C19	119.4 (5)
C2—C1—H1A	109.9	C21—C20—H20	120.3
N2—C1—H1B	109.9	C19—C20—H20	120.3
C2—C1—H1B	109.9	C22—C21—C20	119.3 (5)
H1A—C1—H1B	108.3	C22—C21—H21	120.4
N1—C2—C3	121.9 (5)	C20—C21—H21	120.4
N1—C2—C1	115.4 (4)	C21—C22—C23	119.0 (5)
C3—C2—C1	122.6 (5)	C21—C22—H22	120.5
C4—C3—C2	118.1 (5)	C23—C22—H22	120.5
C4—C3—H3	121.0	N4—C23—C22	122.0 (5)
C2—C3—H3	121.0	N4—C23—H23	119.0
C5—C4—C3	119.9 (5)	C22—C23—H23	119.0
C5—C4—H4	120.1	N5—C24—C25	109.3 (4)
C3—C4—H4	120.1	N5—C24—H24A	109.8
C6—C5—C4	118.4 (5)	C25—C24—H24A	109.8
C6—C5—H5	120.8	N5—C24—H24B	109.8
C4—C5—H5	120.8	C25—C24—H24B	109.8
N1—C6—C5	122.7 (5)	H24A—C24—H24B	108.3
N1—C6—H6	118.6	N6—C25—C26	122.5 (5)
C5—C6—H6	118.6	N6—C25—C24	115.1 (4)
N2—C7—C8	110.7 (4)	C26—C25—C24	122.4 (5)
N2—C7—H7A	109.5	C27—C26—C25	117.9 (6)
C8—C7—H7A	109.5	C27—C26—H26	121.0
N2—C7—H7B	109.5	C25—C26—H26	121.0
C8—C7—H7B	109.5	C28—C27—C26	119.9 (5)
H7A—C7—H7B	108.1	C28—C27—H27	120.0
N3—C8—C9	121.8 (4)	C26—C27—H27	120.0
N3—C8—C7	116.3 (4)	C27—C28—C29	118.7 (5)
C9—C8—C7	121.8 (4)	C27—C28—H28	120.7
C10—C9—C8	119.0 (5)	C29—C28—H28	120.7
C10—C9—H9	120.5	N6—C29—C28	122.5 (5)
C8—C9—H9	120.5	N6—C29—H29	118.8
C9—C10—C11	119.2 (5)	C28—C29—H29	118.8
N3—Cu1—N1—C6	−160.7 (5)	N1—C2—C3—C4	0.6 (7)
N2—Cu1—N1—C6	−163.3 (4)	C1—C2—C3—C4	178.1 (4)
Cl2—Cu1—N1—C6	−12.9 (4)	C2—C3—C4—C5	0.0 (7)
Cl1—Cu1—N1—C6	98.8 (4)	C3—C4—C5—C6	−0.4 (7)
N3—Cu1—N1—C2	25.0 (8)	C2—N1—C6—C5	0.2 (7)
N2—Cu1—N1—C2	22.3 (3)	Cu1—N1—C6—C5	−173.8 (4)
Cl2—Cu1—N1—C2	172.8 (3)	C4—C5—C6—N1	0.3 (7)
Cl1—Cu1—N1—C2	−75.5 (3)	C1—N2—C7—C8	−147.0 (4)
N1—Cu1—N2—C1	−35.2 (3)	C13—N2—C7—C8	90.5 (4)
N3—Cu1—N2—C1	145.6 (3)	Cu1—N2—C7—C8	−33.5 (4)
Cl2—Cu1—N2—C1	−121.5 (3)	C12—N3—C8—C9	−1.1 (7)
Cl1—Cu1—N2—C1	52.2 (3)	Cu1—N3—C8—C9	178.0 (3)
N1—Cu1—N2—C7	−155.4 (3)	C12—N3—C8—C7	177.0 (4)
N3—Cu1—N2—C7	25.4 (3)	Cu1—N3—C8—C7	−3.9 (5)
Cl2—Cu1—N2—C7	118.4 (3)	N2—C7—C8—N3	26.3 (6)
Cl1—Cu1—N2—C7	−68.0 (3)	N2—C7—C8—C9	−155.6 (4)
N1—Cu1—N2—C13	82.6 (3)	N3—C8—C9—C10	0.8 (7)
N3—Cu1—N2—C13	−96.7 (3)	C7—C8—C9—C10	−177.2 (4)
Cl2—Cu1—N2—C13	−3.7 (4)	C8—C9—C10—C11	0.5 (7)
Cl1—Cu1—N2—C13	170.0 (3)	C9—C10—C11—C12	−1.4 (8)
N1—Cu1—N3—C8	−15.3 (8)	C8—N3—C12—C11	0.2 (7)
N2—Cu1—N3—C8	−12.7 (3)	Cu1—N3—C12—C11	−178.8 (4)
Cl2—Cu1—N3—C8	−162.9 (3)	C10—C11—C12—N3	1.1 (8)
Cl1—Cu1—N3—C8	84.4 (3)	C1—N2—C13—C14	168.1 (4)
N1—Cu1—N3—C12	163.7 (5)	C7—N2—C13—C14	−66.4 (5)
N2—Cu1—N3—C12	166.4 (4)	Cu1—N2—C13—C14	53.0 (5)
Cl2—Cu1—N3—C12	16.1 (4)	N2—C13—C14—C15	174.9 (4)
Cl1—Cu1—N3—C12	−96.6 (4)	C13—C14—C15—C16	−171.3 (4)
N6—Cu2—N4—C23	−149.6 (5)	C14—C15—C16—C17	169.4 (4)
N5—Cu2—N4—C23	−166.1 (4)	C24—N5—C17—C16	60.6 (5)
Cl3—Cu2—N4—C23	−12.3 (4)	C18—N5—C17—C16	−68.6 (5)
Cl4—Cu2—N4—C23	97.8 (4)	Cu2—N5—C17—C16	174.8 (3)
N6—Cu2—N4—C19	32.0 (7)	C15—C16—C17—N5	−168.8 (4)
N5—Cu2—N4—C19	15.5 (3)	C24—N5—C18—C19	153.0 (4)
Cl3—Cu2—N4—C19	169.4 (3)	C17—N5—C18—C19	−78.4 (5)
Cl4—Cu2—N4—C19	−80.6 (3)	Cu2—N5—C18—C19	39.0 (4)
N4—Cu2—N5—C24	−150.3 (3)	C23—N4—C19—C20	2.2 (7)
N6—Cu2—N5—C24	34.9 (3)	Cu2—N4—C19—C20	−179.3 (4)
Cl3—Cu2—N5—C24	120.9 (3)	C23—N4—C19—C18	−175.0 (4)
Cl4—Cu2—N5—C24	−57.0 (3)	Cu2—N4—C19—C18	3.5 (5)
N4—Cu2—N5—C17	90.3 (3)	N5—C18—C19—N4	−29.2 (6)
N6—Cu2—N5—C17	−84.6 (3)	N5—C18—C19—C20	153.7 (5)
Cl3—Cu2—N5—C17	1.5 (5)	N4—C19—C20—C21	−2.9 (8)
Cl4—Cu2—N5—C17	−176.5 (3)	C18—C19—C20—C21	174.0 (5)
N4—Cu2—N5—C18	−30.1 (3)	C19—C20—C21—C22	0.9 (9)
N6—Cu2—N5—C18	155.1 (3)	C20—C21—C22—C23	1.7 (8)
Cl3—Cu2—N5—C18	−118.9 (3)	C19—N4—C23—C22	0.5 (8)
Cl4—Cu2—N5—C18	63.2 (3)	Cu2—N4—C23—C22	−177.8 (4)
N4—Cu2—N6—C29	144.3 (5)	C21—C22—C23—N4	−2.5 (8)
N5—Cu2—N6—C29	160.9 (5)	C17—N5—C24—C25	74.5 (5)
Cl3—Cu2—N6—C29	6.9 (4)	C18—N5—C24—C25	−157.0 (4)
Cl4—Cu2—N6—C29	−102.9 (4)	Cu2—N5—C24—C25	−41.7 (4)
N4—Cu2—N6—C25	−39.2 (7)	C29—N6—C25—C26	3.1 (7)
N5—Cu2—N6—C25	−22.6 (3)	Cu2—N6—C25—C26	−173.8 (4)
Cl3—Cu2—N6—C25	−176.6 (3)	C29—N6—C25—C24	−179.3 (4)
Cl4—Cu2—N6—C25	73.6 (3)	Cu2—N6—C25—C24	3.8 (5)
C7—N2—C1—C2	156.6 (4)	N5—C24—C25—N6	26.7 (6)
C13—N2—C1—C2	−79.7 (4)	N5—C24—C25—C26	−155.7 (5)
Cu1—N2—C1—C2	41.8 (4)	N6—C25—C26—C27	−1.0 (8)
C6—N1—C2—C3	−0.7 (7)	C24—C25—C26—C27	−178.4 (5)
Cu1—N1—C2—C3	174.2 (4)	C25—C26—C27—C28	−1.9 (8)
C6—N1—C2—C1	−178.3 (4)	C26—C27—C28—C29	2.6 (8)
Cu1—N1—C2—C1	−3.5 (5)	C25—N6—C29—C28	−2.3 (8)
N2—C1—C2—N1	−27.4 (5)	Cu2—N6—C29—C28	174.0 (4)
N2—C1—C2—C3	154.9 (4)	C27—C28—C29—N6	−0.5 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2WB···Cl1i	0.83 (2)	2.54 (7)	3.270 (8)	147 (11)
O2—H2WA···O1ii	0.84 (2)	2.46 (4)	3.249 (11)	157 (10)
O1—H1WB···Cl2iii	0.84 (2)	2.54 (4)	3.335 (6)	159 (8)
O1—H1WA···Cl4iv	0.84 (2)	2.47 (3)	3.306 (6)	169 (10)

Table 1

Selected bond lengths (Å)

Cu1—N1	1.986 (4)
Cu1—N3	1.996 (4)
Cu1—N2	2.076 (4)
Cu1—Cl2	2.2832 (13)
Cu1—Cl1	2.5261 (13)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2WB⋯Cl1i	0.83 (2)	2.54 (7)	3.270 (8)	147 (11)
O2—H2WA⋯O1ii	0.84 (2)	2.46 (4)	3.249 (11)	157 (10)
O1—H1WB⋯Cl2iii	0.84 (2)	2.54 (4)	3.335 (6)	159 (8)
O1—H1WA⋯Cl4iv	0.84 (2)	2.47 (3)	3.306 (6)	169 (10)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .