Bis[N-benzyl-2-(quinolin-8-yl-oxy)acetamide]dichloridocopper(II) acetonitrile solvate monohydrate.

In the title complex, [CuCl(2)(C(18)H(16)N(2)O(2))(2)]·CH(3)CN·H(2)O, the six-coordinated Cu atom is in a distorted octa-hedral geometry with the donor centers of two O atoms and two N atom from two bidentate ligands, and two chloride ions. In the crystal, pairs of inter-molecular N-H⋯ Cl hydrogen bonds form centrosymmetric dimers and inter-molecular O-H⋯ O hydrogen bonds between the ligand and the uncoordinated water mol-ecules link the dimers into chains parallel to the c axis.

Related literature

For the synthesis of N-phenyl-2-(quinolin-8-yl­oxy)acetamide, see Wu, Yuan et al. (2006 ▶); Wu et al. (2008 ▶). For related structures, see: Al-Mandhary & Steel (2002 ▶); Wu, Wang et al. (2006 ▶); Zhu et al. (2005 ▶).

Experimental

Crystal data

[CuCl2(C18H16N2O2)2]·C2H3N·H2O

M = 778.17

Triclinic,

a = 10.202 (3) Å

b = 13.253 (4) Å

c = 14.009 (4) Å

α = 78.927 (3)°

β = 78.995 (3)°

γ = 86.366 (3)°

V = 1824.0 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.80 mm−1

T = 293 K

0.31 × 0.21 × 0.13 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.818, T max = 0.902

19499 measured reflections

7457 independent reflections

4374 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.186

S = 1.03

7457 reflections

464 parameters

9 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.71 e Å−3

Δρmin = −0.85 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536810005453/vm2018sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005453/vm2018Isup2.hkl

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

[CuCl2(C18H16N2O2)2]·C2H3N·H2O	V = 1824.0 (9) Å3
Mr = 778.17	Z = 2
Triclinic, P1	F(000) = 806
Hall symbol: -P 1	Dx = 1.417 Mg m−3
a = 10.202 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.253 (4) Å	θ = 2.0–26.5°
c = 14.009 (4) Å	µ = 0.80 mm−1
α = 78.927 (3)°	T = 293 K
β = 78.995 (3)°	Block, blue
γ = 86.366 (3)°	0.31 × 0.21 × 0.13 mm

Bruker SMART CCD diffractometer	7457 independent reflections
Radiation source: fine-focus sealed tube	4374 reflections with I > 2σ(I)
graphite	Rint = 0.059
phi and ω scans	θmax = 26.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.818, Tmax = 0.902	k = −16→16
19499 measured reflections	l = −17→17

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.1001P)2] where P = (Fo2 + 2Fc2)/3
7457 reflections	(Δ/σ)max = 0.030
464 parameters	Δρmax = 0.71 e Å−3
9 restraints	Δρmin = −0.85 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.70023 (5)	0.29872 (4)	0.40084 (4)	0.04355 (19)
O1	0.6634 (3)	0.3689 (2)	0.5515 (2)	0.0474 (7)
O2	0.5770 (4)	0.2507 (2)	0.7300 (2)	0.0658 (9)
O3	0.7440 (3)	0.1992 (2)	0.2675 (2)	0.0558 (8)
O4	0.6412 (5)	0.2161 (4)	0.0407 (3)	0.1052 (15)
N1	0.8765 (3)	0.3017 (3)	0.4417 (3)	0.0461 (8)
N2	0.4376 (4)	0.3748 (3)	0.7784 (3)	0.0571 (10)
H2A	0.4049	0.4354	0.7603	0.068*
N3	0.6864 (3)	0.1485 (3)	0.4624 (3)	0.0450 (8)
N4	0.5215 (5)	0.2459 (4)	0.1848 (3)	0.0731 (13)
H4A	0.5265	0.2605	0.2412	0.088*
C1	0.9814 (5)	0.2679 (4)	0.3872 (4)	0.0631 (13)
H1	0.9699	0.2367	0.3354	0.076*
C2	1.1110 (5)	0.2766 (5)	0.4033 (5)	0.0812 (17)
H2	1.1840	0.2509	0.3635	0.097*
C3	1.1281 (5)	0.3220 (5)	0.4762 (5)	0.0744 (16)
H3	1.2141	0.3292	0.4868	0.089*
C4	1.0206 (5)	0.3584 (4)	0.5365 (4)	0.0588 (13)
C5	1.0327 (6)	0.4074 (5)	0.6140 (4)	0.0757 (16)
H5	1.1167	0.4153	0.6277	0.091*
C6	0.9250 (6)	0.4426 (4)	0.6681 (4)	0.0766 (17)
H6	0.9347	0.4752	0.7194	0.092*
C7	0.7977 (5)	0.4320 (4)	0.6499 (4)	0.0639 (14)
H7	0.7236	0.4577	0.6886	0.077*
C8	0.7817 (4)	0.3850 (3)	0.5768 (3)	0.0486 (11)
C9	0.8941 (4)	0.3470 (3)	0.5172 (3)	0.0459 (10)
C10	0.5454 (4)	0.3984 (3)	0.6105 (3)	0.0491 (11)
H10A	0.4703	0.3927	0.5788	0.059*
H10B	0.5504	0.4698	0.6161	0.059*
C11	0.5224 (4)	0.3329 (3)	0.7126 (3)	0.0471 (10)
C12	0.3973 (5)	0.3233 (4)	0.8795 (3)	0.0656 (14)
H12A	0.3773	0.3747	0.9215	0.079*
H12B	0.4717	0.2808	0.8998	0.079*
C13	0.2795 (6)	0.2578 (4)	0.8961 (3)	0.0618 (13)
C14	0.2840 (7)	0.1598 (5)	0.9468 (4)	0.0849 (18)
H14	0.3629	0.1326	0.9666	0.102*
C15	0.1726 (10)	0.1004 (6)	0.9691 (6)	0.113 (3)
H15	0.1765	0.0334	1.0041	0.136*
C16	0.0591 (9)	0.1384 (6)	0.9409 (6)	0.120 (3)
H16	−0.0164	0.0984	0.9575	0.143*
C17	0.0531 (7)	0.2365 (5)	0.8872 (6)	0.102 (2)
H17	−0.0255	0.2627	0.8664	0.123*
C18	0.1644 (6)	0.2949 (4)	0.8650 (5)	0.0769 (16)
H18	0.1613	0.3610	0.8280	0.092*
C19	0.6631 (4)	0.1215 (3)	0.5579 (4)	0.0518 (11)
H19	0.6587	0.1728	0.5954	0.062*
C20	0.6444 (5)	0.0211 (4)	0.6076 (4)	0.0583 (12)
H20	0.6281	0.0062	0.6764	0.070*
C21	0.6501 (5)	−0.0535 (4)	0.5556 (4)	0.0599 (13)
H21	0.6381	−0.1213	0.5880	0.072*
C22	0.6738 (4)	−0.0304 (3)	0.4537 (4)	0.0534 (12)
C23	0.6761 (5)	−0.1045 (4)	0.3929 (5)	0.0688 (15)
H23	0.6622	−0.1732	0.4217	0.083*
C24	0.6977 (6)	−0.0771 (4)	0.2949 (5)	0.0734 (15)
H24	0.6991	−0.1270	0.2562	0.088*
C25	0.7184 (5)	0.0248 (4)	0.2495 (4)	0.0693 (14)
H25	0.7316	0.0428	0.1809	0.083*
C26	0.7196 (4)	0.0979 (3)	0.3047 (4)	0.0519 (11)
C27	0.6934 (4)	0.0720 (3)	0.4085 (3)	0.0446 (10)
C28	0.7583 (5)	0.2327 (4)	0.1643 (4)	0.0724 (15)
H28A	0.8260	0.1897	0.1317	0.087*
H28B	0.7899	0.3025	0.1478	0.087*
C29	0.6328 (7)	0.2302 (4)	0.1244 (4)	0.0740 (15)
C30	0.3922 (6)	0.2396 (4)	0.1612 (4)	0.0781 (16)
H30A	0.3363	0.1996	0.2179	0.094*
H30B	0.4014	0.2024	0.1069	0.094*
C31	0.3221 (5)	0.3406 (4)	0.1332 (3)	0.0636 (13)
C32	0.1919 (5)	0.3386 (5)	0.1231 (4)	0.0737 (15)
H32	0.1485	0.2765	0.1365	0.088*
C33	0.1260 (7)	0.4277 (6)	0.0935 (5)	0.0914 (19)
H33	0.0374	0.4259	0.0863	0.110*
C34	0.1867 (7)	0.5199 (6)	0.0740 (5)	0.096 (2)
H34	0.1411	0.5806	0.0528	0.115*
C35	0.3143 (6)	0.5212 (5)	0.0862 (4)	0.0838 (17)
H35	0.3564	0.5838	0.0742	0.101*
C36	0.3830 (6)	0.4332 (4)	0.1155 (4)	0.0748 (15)
H36	0.4710	0.4359	0.1236	0.090*
Cl1	0.75545 (12)	0.43895 (9)	0.28587 (10)	0.0660 (4)
Cl2	0.47968 (10)	0.31446 (8)	0.39799 (8)	0.0498 (3)
C38	0.9313 (9)	0.0002 (7)	0.7221 (8)	0.136 (3)
N5	0.9214 (10)	−0.0854 (7)	0.7463 (8)	0.184 (4)
C37	0.9421 (9)	0.1096 (6)	0.6906 (8)	0.165 (4)
H37A	1.0198	0.1318	0.7091	0.198*
H37B	0.8639	0.1434	0.7216	0.198*
H37C	0.9495	0.1266	0.6200	0.198*
O1W	0.6967 (15)	0.1253 (12)	0.8737 (6)	0.369 (9)
H1WA	0.6468	0.1607	0.8369	0.554*
H1WB	0.651 (9)	0.110 (18)	0.933 (5)	0.554*

	U11	U22	U33	U12	U13	U23
Cu1	0.0433 (3)	0.0369 (3)	0.0527 (4)	0.0014 (2)	−0.0148 (2)	−0.0086 (2)
O1	0.0442 (16)	0.0527 (18)	0.0462 (17)	−0.0022 (13)	−0.0043 (13)	−0.0152 (14)
O2	0.087 (3)	0.045 (2)	0.059 (2)	0.0147 (18)	−0.0079 (18)	−0.0071 (16)
O3	0.068 (2)	0.0501 (19)	0.050 (2)	0.0027 (15)	−0.0122 (15)	−0.0093 (15)
O4	0.139 (4)	0.132 (4)	0.052 (3)	0.017 (3)	−0.029 (2)	−0.029 (2)
N1	0.044 (2)	0.042 (2)	0.052 (2)	0.0022 (16)	−0.0071 (17)	−0.0099 (17)
N2	0.065 (3)	0.054 (2)	0.049 (2)	0.0007 (19)	−0.0003 (19)	−0.0117 (19)
N3	0.045 (2)	0.043 (2)	0.051 (2)	0.0040 (15)	−0.0161 (16)	−0.0106 (17)
N4	0.083 (3)	0.089 (3)	0.056 (3)	0.017 (3)	−0.030 (3)	−0.024 (2)
C1	0.056 (3)	0.067 (3)	0.066 (3)	0.009 (2)	−0.011 (2)	−0.015 (3)
C2	0.046 (3)	0.103 (5)	0.089 (4)	0.018 (3)	−0.010 (3)	−0.011 (4)
C3	0.044 (3)	0.091 (4)	0.086 (4)	−0.007 (3)	−0.024 (3)	0.004 (3)
C4	0.047 (3)	0.060 (3)	0.067 (3)	−0.009 (2)	−0.021 (2)	0.006 (2)
C5	0.071 (4)	0.092 (4)	0.072 (4)	−0.027 (3)	−0.033 (3)	−0.007 (3)
C6	0.097 (5)	0.082 (4)	0.060 (3)	−0.036 (4)	−0.028 (3)	−0.009 (3)
C7	0.082 (4)	0.065 (3)	0.051 (3)	−0.017 (3)	−0.014 (3)	−0.020 (2)
C8	0.057 (3)	0.046 (3)	0.045 (3)	−0.014 (2)	−0.013 (2)	−0.004 (2)
C9	0.046 (2)	0.044 (2)	0.048 (3)	−0.0065 (19)	−0.013 (2)	−0.002 (2)
C10	0.049 (3)	0.048 (3)	0.048 (3)	0.005 (2)	−0.003 (2)	−0.010 (2)
C11	0.053 (3)	0.042 (3)	0.047 (3)	−0.005 (2)	−0.007 (2)	−0.008 (2)
C12	0.077 (3)	0.073 (3)	0.046 (3)	−0.006 (3)	−0.006 (2)	−0.013 (3)
C13	0.084 (4)	0.056 (3)	0.045 (3)	−0.007 (3)	−0.001 (3)	−0.017 (2)
C14	0.124 (5)	0.066 (4)	0.070 (4)	−0.002 (4)	−0.030 (4)	−0.014 (3)
C15	0.153 (8)	0.076 (5)	0.107 (6)	−0.045 (5)	−0.020 (6)	0.002 (4)
C16	0.127 (7)	0.096 (6)	0.131 (7)	−0.060 (5)	0.006 (6)	−0.020 (5)
C17	0.083 (5)	0.079 (5)	0.146 (7)	−0.016 (4)	−0.013 (4)	−0.027 (5)
C18	0.080 (4)	0.055 (3)	0.093 (4)	−0.012 (3)	−0.006 (3)	−0.013 (3)
C19	0.058 (3)	0.042 (3)	0.058 (3)	0.007 (2)	−0.017 (2)	−0.013 (2)
C20	0.065 (3)	0.049 (3)	0.060 (3)	0.003 (2)	−0.019 (2)	−0.001 (2)
C21	0.063 (3)	0.039 (3)	0.079 (4)	0.003 (2)	−0.026 (3)	−0.002 (2)
C22	0.045 (3)	0.040 (3)	0.079 (4)	0.0042 (19)	−0.023 (2)	−0.011 (2)
C23	0.076 (4)	0.040 (3)	0.100 (5)	0.008 (2)	−0.026 (3)	−0.030 (3)
C24	0.088 (4)	0.054 (3)	0.091 (4)	0.010 (3)	−0.029 (3)	−0.034 (3)
C25	0.083 (4)	0.062 (3)	0.070 (4)	0.013 (3)	−0.023 (3)	−0.025 (3)
C26	0.055 (3)	0.042 (3)	0.064 (3)	0.009 (2)	−0.017 (2)	−0.017 (2)
C27	0.041 (2)	0.037 (2)	0.060 (3)	0.0052 (18)	−0.018 (2)	−0.015 (2)
C28	0.079 (4)	0.078 (4)	0.056 (3)	0.003 (3)	−0.004 (3)	−0.013 (3)
C29	0.101 (5)	0.073 (4)	0.052 (3)	0.007 (3)	−0.023 (3)	−0.013 (3)
C30	0.092 (4)	0.077 (4)	0.074 (4)	0.002 (3)	−0.033 (3)	−0.017 (3)
C31	0.074 (4)	0.075 (4)	0.047 (3)	0.005 (3)	−0.019 (2)	−0.018 (3)
C32	0.069 (4)	0.087 (4)	0.067 (4)	−0.004 (3)	−0.019 (3)	−0.011 (3)
C33	0.077 (4)	0.114 (6)	0.089 (5)	0.006 (4)	−0.024 (3)	−0.027 (4)
C34	0.107 (6)	0.100 (5)	0.084 (5)	0.028 (4)	−0.030 (4)	−0.025 (4)
C35	0.098 (5)	0.072 (4)	0.082 (4)	−0.007 (4)	−0.016 (4)	−0.016 (3)
C36	0.070 (4)	0.079 (4)	0.079 (4)	−0.005 (3)	−0.021 (3)	−0.016 (3)
Cl1	0.0627 (8)	0.0501 (7)	0.0804 (9)	−0.0065 (6)	−0.0203 (6)	0.0085 (6)
Cl2	0.0443 (6)	0.0460 (6)	0.0630 (7)	0.0010 (5)	−0.0165 (5)	−0.0138 (5)
C38	0.113 (7)	0.118 (7)	0.183 (10)	−0.006 (6)	−0.049 (6)	−0.018 (8)
N5	0.208 (10)	0.119 (7)	0.213 (10)	−0.002 (7)	−0.003 (7)	−0.038 (7)
C37	0.155 (8)	0.110 (7)	0.233 (12)	−0.035 (6)	−0.092 (8)	0.030 (7)
O1W	0.487 (18)	0.438 (17)	0.168 (8)	0.350 (16)	−0.110 (10)	−0.086 (10)

Cu1—N1	1.993 (3)	C15—C16	1.333 (10)
Cu1—N3	2.014 (3)	C15—H15	0.9300
Cu1—Cl1	2.2364 (13)	C16—C17	1.375 (10)
Cu1—Cl2	2.2537 (13)	C16—H16	0.9300
Cu1—O1	2.423 (3)	C17—C18	1.367 (8)
O1—C8	1.360 (5)	C17—H17	0.9300
O1—C10	1.404 (5)	C18—H18	0.9300
O2—C11	1.196 (5)	C19—C20	1.384 (6)
O3—C26	1.363 (5)	C19—H19	0.9300
O3—C28	1.410 (6)	C20—C21	1.329 (7)
O4—C29	1.208 (6)	C20—H20	0.9300
N1—C1	1.299 (6)	C21—C22	1.379 (7)
N1—C9	1.357 (5)	C21—H21	0.9300
N2—C11	1.318 (5)	C22—C27	1.393 (6)
N2—C12	1.444 (6)	C22—C23	1.415 (7)
N2—H2A	0.8600	C23—C24	1.329 (7)
N3—C19	1.296 (5)	C23—H23	0.9300
N3—C27	1.367 (5)	C24—C25	1.389 (7)
N4—C29	1.311 (7)	C24—H24	0.9300
N4—C30	1.431 (7)	C25—C26	1.354 (6)
N4—H4A	0.8600	C25—H25	0.9300
C1—C2	1.399 (7)	C26—C27	1.405 (6)
C1—H1	0.9300	C28—C29	1.497 (8)
C2—C3	1.324 (8)	C28—H28A	0.9700
C2—H2	0.9300	C28—H28B	0.9700
C3—C4	1.374 (7)	C30—C31	1.497 (7)
C3—H3	0.9300	C30—H30A	0.9700
C4—C9	1.390 (6)	C30—H30B	0.9700
C4—C5	1.395 (7)	C31—C32	1.365 (6)
C5—C6	1.323 (8)	C31—C36	1.370 (6)
C5—H5	0.9300	C32—C33	1.355 (8)
C6—C7	1.392 (7)	C32—H32	0.9300
C6—H6	0.9300	C33—C34	1.362 (7)
C7—C8	1.336 (6)	C33—H33	0.9300
C7—H7	0.9300	C34—C35	1.346 (7)
C8—C9	1.410 (6)	C34—H34	0.9300
C10—C11	1.507 (6)	C35—C36	1.356 (6)
C10—H10A	0.9700	C35—H35	0.9300
C10—H10B	0.9700	C36—H36	0.9300
C12—C13	1.483 (7)	C38—N5	1.125 (10)
C12—H12A	0.9700	C38—C37	1.436 (8)
C12—H12B	0.9700	C37—H37A	0.9600
C13—C14	1.359 (7)	C37—H37B	0.9600
C13—C18	1.360 (8)	C37—H37C	0.9600
C14—C15	1.375 (9)	O1W—H1WA	0.8501
C14—H14	0.9300	O1W—H1WB	0.86 (2)
N1—Cu1—N3	89.95 (13)	C15—C16—C17	120.3 (7)
N1—Cu1—Cl1	89.01 (11)	C15—C16—H16	119.8
N3—Cu1—Cl1	158.68 (11)	C17—C16—H16	119.8
N1—Cu1—Cl2	162.28 (11)	C18—C17—C16	119.1 (7)
N3—Cu1—Cl2	92.14 (10)	C18—C17—H17	120.5
Cl1—Cu1—Cl2	95.29 (5)	C16—C17—H17	120.5
N1—Cu1—O1	72.19 (12)	C13—C18—C17	121.0 (6)
N3—Cu1—O1	98.37 (12)	C13—C18—H18	119.5
Cl1—Cu1—O1	101.57 (8)	C17—C18—H18	119.5
Cl2—Cu1—O1	90.10 (7)	N3—C19—C20	124.2 (4)
C8—O1—C10	117.9 (3)	N3—C19—H19	117.9
C8—O1—Cu1	110.8 (2)	C20—C19—H19	117.9
C10—O1—Cu1	131.3 (3)	C21—C20—C19	119.0 (5)
C26—O3—C28	118.1 (4)	C21—C20—H20	120.5
C1—N1—C9	118.3 (4)	C19—C20—H20	120.5
C1—N1—Cu1	118.1 (3)	C20—C21—C22	120.0 (5)
C9—N1—Cu1	123.1 (3)	C20—C21—H21	120.0
C11—N2—C12	122.7 (4)	C22—C21—H21	120.0
C11—N2—H2A	118.6	C21—C22—C27	117.9 (4)
C12—N2—H2A	118.6	C21—C22—C23	123.7 (5)
C19—N3—C27	117.1 (4)	C27—C22—C23	118.4 (5)
C19—N3—Cu1	119.6 (3)	C24—C23—C22	120.8 (5)
C27—N3—Cu1	123.3 (3)	C24—C23—H23	119.6
C29—N4—C30	123.0 (5)	C22—C23—H23	119.6
C29—N4—H4A	118.5	C23—C24—C25	121.0 (5)
C30—N4—H4A	118.5	C23—C24—H24	119.5
N1—C1—C2	122.6 (5)	C25—C24—H24	119.5
N1—C1—H1	118.7	C26—C25—C24	120.2 (5)
C2—C1—H1	118.7	C26—C25—H25	119.9
C3—C2—C1	119.0 (5)	C24—C25—H25	119.9
C3—C2—H2	120.5	C25—C26—O3	124.9 (5)
C1—C2—H2	120.5	C25—C26—C27	120.1 (4)
C2—C3—C4	120.8 (5)	O3—C26—C27	115.0 (4)
C2—C3—H3	119.6	N3—C27—C22	121.7 (4)
C4—C3—H3	119.6	N3—C27—C26	118.9 (4)
C3—C4—C9	117.6 (5)	C22—C27—C26	119.3 (4)
C3—C4—C5	123.3 (5)	O3—C28—C29	114.4 (4)
C9—C4—C5	119.2 (5)	O3—C28—H28A	108.7
C6—C5—C4	120.3 (5)	C29—C28—H28A	108.7
C6—C5—H5	119.9	O3—C28—H28B	108.7
C4—C5—H5	119.9	C29—C28—H28B	108.7
C5—C6—C7	121.4 (5)	H28A—C28—H28B	107.6
C5—C6—H6	119.3	O4—C29—N4	125.7 (6)
C7—C6—H6	119.3	O4—C29—C28	118.8 (6)
C8—C7—C6	120.2 (5)	N4—C29—C28	115.5 (5)
C8—C7—H7	119.9	N4—C30—C31	115.4 (5)
C6—C7—H7	119.9	N4—C30—H30A	108.4
C7—C8—O1	126.2 (4)	C31—C30—H30A	108.4
C7—C8—C9	120.0 (4)	N4—C30—H30B	108.4
O1—C8—C9	113.8 (4)	C31—C30—H30B	108.4
N1—C9—C4	121.7 (4)	H30A—C30—H30B	107.5
N1—C9—C8	119.3 (4)	C32—C31—C36	119.2 (5)
C4—C9—C8	119.0 (4)	C32—C31—C30	117.5 (5)
O1—C10—C11	111.9 (4)	C36—C31—C30	123.3 (5)
O1—C10—H10A	109.2	C33—C32—C31	119.7 (6)
C11—C10—H10A	109.2	C33—C32—H32	120.1
O1—C10—H10B	109.2	C31—C32—H32	120.1
C11—C10—H10B	109.2	C32—C33—C34	121.3 (6)
H10A—C10—H10B	107.9	C32—C33—H33	119.3
O2—C11—N2	124.5 (4)	C34—C33—H33	119.3
O2—C11—C10	121.8 (4)	C35—C34—C33	118.5 (6)
N2—C11—C10	113.7 (4)	C35—C34—H34	120.8
N2—C12—C13	114.3 (4)	C33—C34—H34	120.8
N2—C12—H12A	108.7	C34—C35—C36	121.5 (6)
C13—C12—H12A	108.7	C34—C35—H35	119.2
N2—C12—H12B	108.7	C36—C35—H35	119.2
C13—C12—H12B	108.7	C35—C36—C31	119.7 (5)
H12A—C12—H12B	107.6	C35—C36—H36	120.1
C14—C13—C18	118.8 (6)	C31—C36—H36	120.1
C14—C13—C12	119.6 (6)	N5—C38—C37	179.1 (12)
C18—C13—C12	121.5 (5)	C38—C37—H37A	109.5
C13—C14—C15	120.5 (7)	C38—C37—H37B	109.5
C13—C14—H14	119.8	H37A—C37—H37B	109.5
C15—C14—H14	119.8	C38—C37—H37C	109.5
C16—C15—C14	120.3 (7)	H37A—C37—H37C	109.5
C16—C15—H15	119.9	H37B—C37—H37C	109.5
C14—C15—H15	119.9	H1WA—O1W—H1WB	108.6
N1—Cu1—O1—C8	7.6 (3)	O1—C10—C11—O2	−19.0 (6)
N3—Cu1—O1—C8	94.8 (3)	O1—C10—C11—N2	161.3 (4)
Cl1—Cu1—O1—C8	−77.6 (3)	C11—N2—C12—C13	−88.6 (6)
Cl2—Cu1—O1—C8	−173.0 (2)	N2—C12—C13—C14	131.0 (5)
N1—Cu1—O1—C10	−175.8 (4)	N2—C12—C13—C18	−51.7 (7)
N3—Cu1—O1—C10	−88.6 (3)	C18—C13—C14—C15	−2.2 (9)
Cl1—Cu1—O1—C10	99.0 (3)	C12—C13—C14—C15	175.3 (5)
Cl2—Cu1—O1—C10	3.6 (3)	C13—C14—C15—C16	0.2 (11)
N3—Cu1—N1—C1	80.9 (4)	C14—C15—C16—C17	1.5 (13)
Cl1—Cu1—N1—C1	−77.8 (3)	C15—C16—C17—C18	−1.2 (12)
Cl2—Cu1—N1—C1	177.8 (3)	C14—C13—C18—C17	2.5 (9)
O1—Cu1—N1—C1	179.8 (4)	C12—C13—C18—C17	−174.9 (5)
N3—Cu1—N1—C9	−106.3 (3)	C16—C17—C18—C13	−0.8 (10)
Cl1—Cu1—N1—C9	95.0 (3)	C27—N3—C19—C20	−0.4 (6)
Cl2—Cu1—N1—C9	−9.4 (6)	Cu1—N3—C19—C20	176.3 (3)
O1—Cu1—N1—C9	−7.5 (3)	N3—C19—C20—C21	−0.1 (7)
N1—Cu1—N3—C19	72.2 (3)	C19—C20—C21—C22	−0.2 (7)
Cl1—Cu1—N3—C19	159.3 (3)	C20—C21—C22—C27	1.0 (7)
Cl2—Cu1—N3—C19	−90.2 (3)	C20—C21—C22—C23	−177.3 (5)
O1—Cu1—N3—C19	0.2 (3)	C21—C22—C23—C24	179.1 (5)
N1—Cu1—N3—C27	−111.3 (3)	C27—C22—C23—C24	0.7 (7)
Cl1—Cu1—N3—C27	−24.2 (5)	C22—C23—C24—C25	−0.2 (8)
Cl2—Cu1—N3—C27	86.3 (3)	C23—C24—C25—C26	1.4 (8)
O1—Cu1—N3—C27	176.7 (3)	C24—C25—C26—O3	177.4 (4)
C9—N1—C1—C2	0.0 (7)	C24—C25—C26—C27	−3.1 (7)
Cu1—N1—C1—C2	173.1 (4)	C28—O3—C26—C25	5.5 (7)
N1—C1—C2—C3	−0.8 (9)	C28—O3—C26—C27	−174.0 (4)
C1—C2—C3—C4	1.2 (9)	C19—N3—C27—C22	1.3 (6)
C2—C3—C4—C9	−0.8 (8)	Cu1—N3—C27—C22	−175.3 (3)
C2—C3—C4—C5	−179.6 (5)	C19—N3—C27—C26	−179.5 (4)
C3—C4—C5—C6	178.6 (5)	Cu1—N3—C27—C26	4.0 (5)
C9—C4—C5—C6	−0.2 (8)	C21—C22—C27—N3	−1.6 (6)
C4—C5—C6—C7	0.1 (9)	C23—C22—C27—N3	176.9 (4)
C5—C6—C7—C8	0.3 (8)	C21—C22—C27—C26	179.2 (4)
C6—C7—C8—O1	179.5 (4)	C23—C22—C27—C26	−2.4 (6)
C6—C7—C8—C9	−0.7 (7)	C25—C26—C27—N3	−175.7 (4)
C10—O1—C8—C7	−4.1 (6)	O3—C26—C27—N3	3.9 (6)
Cu1—O1—C8—C7	173.0 (4)	C25—C26—C27—C22	3.6 (7)
C10—O1—C8—C9	176.2 (3)	O3—C26—C27—C22	−176.8 (4)
Cu1—O1—C8—C9	−6.7 (4)	C26—O3—C28—C29	68.0 (6)
C1—N1—C9—C4	0.4 (6)	C30—N4—C29—O4	5.4 (9)
Cu1—N1—C9—C4	−172.3 (3)	C30—N4—C29—C28	−175.8 (5)
C1—N1—C9—C8	179.5 (4)	O3—C28—C29—O4	−150.3 (5)
Cu1—N1—C9—C8	6.7 (5)	O3—C28—C29—N4	30.9 (7)
C3—C4—C9—N1	0.0 (7)	C29—N4—C30—C31	−104.2 (6)
C5—C4—C9—N1	178.8 (4)	N4—C30—C31—C32	−171.4 (5)
C3—C4—C9—C8	−179.1 (4)	N4—C30—C31—C36	10.1 (8)
C5—C4—C9—C8	−0.2 (7)	C36—C31—C32—C33	1.6 (8)
C7—C8—C9—N1	−178.4 (4)	C30—C31—C32—C33	−177.0 (5)
O1—C8—C9—N1	1.4 (6)	C31—C32—C33—C34	−0.5 (9)
C7—C8—C9—C4	0.7 (7)	C32—C33—C34—C35	−0.9 (10)
O1—C8—C9—C4	−179.6 (4)	C33—C34—C35—C36	1.1 (10)
C8—O1—C10—C11	−67.7 (5)	C34—C35—C36—C31	0.1 (9)
Cu1—O1—C10—C11	115.9 (4)	C32—C31—C36—C35	−1.4 (8)
C12—N2—C11—O2	−2.3 (7)	C30—C31—C36—C35	177.1 (5)
C12—N2—C11—C10	177.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1i	0.86	2.35	3.160 (4)	158
N4—H4A···Cl2	0.86	2.39	3.230 (5)	165
O1W—H1WA···O2	0.85	1.95	2.776 (8)	165
O1W—H1WB···O4ii	0.86 (2)	2.2 (2)	2.781 (11)	121 (23)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Cl1i	0.86	2.35	3.160 (4)	158
N4—H4A⋯Cl2	0.86	2.39	3.230 (5)	165
O1W—H1WA⋯O2	0.85	1.95	2.776 (8)	165
O1W—H1WB⋯O4ii	0.86 (2)	2.2 (2)	2.781 (11)	121 (23)

Symmetry codes: (i) ; (ii) .