Chlorido[1H-1,2,4-triazole-5(4H)-thione-κS]bis-(triphenyl-phosphane-κP)copper(I) acetronitrile monosolvate.

In the title solvate, [CuCl(C2H3N3S)(C18H15P)2]·CH3CN, the Cu(I) ion is bonded to two triphenyl-phosphane ligands, one 1H-1,2,4-triazole-5(4H)-thione ligand via its S atom and one chloride ion in a distorted CuP2SCl tetra-hedron. An intra-molecular N-H⋯Cl hydrogen bond, which closes an S(6) ring, helps to establish the conformation of the complex. In the crystal, N-H⋯Cl hydrogen bonds and C-H⋯π inter-actions link the components, generating (110) layers.

Related literature

For the properties of mixed-ligand class="Chemical">copper(I) complexes, see: Oshio et al. (1996 ▶); Heclass="Chemical">nary et al. (1997 ▶); Vitale & Ford (2001 ▶); Zhaclass="Chemical">ng & Checlass="Chemical">n (2003 ▶). For structurally related mixed-ligaclass="Chemical">nd complexes of tripheclass="Chemical">nyl­phosphaclass="Chemical">ne aclass="Chemical">nd class="Chemical">n class="Chemical">thione ligands, see: Skoulika et al. (1991 ▶); Aslanidis et al. (1998 ▶); Chen et al. (2001 ▶); Li et al. (2004 ▶); Lobana et al. (2008 ▶); La-o et al. (2009 ▶). For complexes of 1,2,4-triazole-2-thione and its derivatives, see: Sen et al. (1996 ▶); Zhang et al. (2008 ▶).

Experimental

Crystal data

[n class="Chemical">CuCl(C2class="Chemical">n class="Species">H3N3S)(C18H15P)2]·C2H3N

M = 765.72

Orthorhombic,

a = 10.2348 (4) Å

b = 16.4046 (7) Å

c = 22.3632 (9) Å

V = 3754.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.83 mm−1

T = 293 K

0.27 × 0.18 × 0.09 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.840, T max = 0.928

30968 measured reflections

6602 independent reflections

6040 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.086

S = 1.11

6602 reflections

449 parameters

2 restraints

n class="Disease">H atoms treated by a mixture of iclass="Chemical">ndepeclass="Chemical">ndeclass="Chemical">nt aclass="Chemical">nd coclass="Chemical">nstraiclass="Chemical">ned reficlass="Chemical">nemeclass="Chemical">nt

Δρmax = 0.52 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 2890 Friedel pairs

Flack parameter: −0.001 (11)

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT (Bruker, 2003 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶), PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812049537/hb7008sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049537/hb7008Isup2.hkl

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

[CuCl(C2H3N3S)(C18H15P)2]·C2H3N	F(000) = 1584
Mr = 765.72	Dx = 1.355 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5583 reflections
a = 10.2348 (4) Å	θ = 2.2–21.3°
b = 16.4046 (7) Å	µ = 0.83 mm−1
c = 22.3632 (9) Å	T = 293 K
V = 3754.7 (3) Å3	Polyhedron, colourless
Z = 4	0.27 × 0.18 × 0.09 mm

Bruker APEX CCD diffractometer	6602 independent reflections
Radiation source: fine-focus sealed tube	6040 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Frames, each covering 0.3 ° in ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −12→12
Tmin = 0.840, Tmax = 0.928	k = −19→19
30968 measured reflections	l = −26→26

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.0419P)2 + 0.5093P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
6602 reflections	Δρmax = 0.52 e Å−3
449 parameters	Δρmin = −0.17 e Å−3
2 restraints	Absolute structure: Flack (1983), 2890 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.001 (11)

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 > 2σ(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	0.34524 (4)	0.93751 (2)	0.962685 (16)	0.03712 (11)
Cl1	0.12918 (7)	0.90194 (5)	0.92963 (4)	0.04224 (19)
S1	0.46576 (9)	0.82003 (6)	0.98819 (5)	0.0529 (2)
P1	0.29805 (8)	1.00323 (5)	1.04989 (3)	0.03605 (19)
P2	0.42531 (8)	0.99058 (5)	0.87575 (4)	0.03542 (19)
N1	0.4062 (3)	0.65928 (17)	0.98402 (14)	0.0466 (7)
N2	0.3204 (3)	0.60429 (17)	0.96044 (14)	0.0533 (7)
N3	0.2723 (3)	0.72977 (17)	0.93421 (14)	0.0440 (7)
C1	0.4369 (3)	1.0231 (2)	1.09970 (16)	0.0449 (8)
C2	0.5549 (4)	1.0419 (2)	1.0752 (2)	0.0615 (11)
H2	0.5638	1.0455	1.0339	0.074*
C3	0.6623 (4)	1.0557 (3)	1.1121 (3)	0.0848 (15)
H3	0.7421	1.0703	1.0953	0.102*
C4	0.6519 (6)	1.0481 (3)	1.1714 (3)	0.0953 (18)
H4	0.7251	1.0549	1.1955	0.114*
C5	0.5345 (7)	1.0306 (4)	1.1963 (3)	0.114 (2)
H5	0.5264	1.0271	1.2377	0.136*
C6	0.4271 (5)	1.0178 (3)	1.16028 (19)	0.0840 (15)
H6	0.3469	1.0055	1.1776	0.101*
C7	0.1835 (3)	0.9471 (2)	1.09762 (14)	0.0401 (8)
C8	0.1875 (4)	0.8625 (2)	1.09702 (16)	0.0509 (9)
H8	0.2479	0.8356	1.0730	0.061*
C9	0.1017 (4)	0.8182 (3)	1.13215 (18)	0.0651 (12)
H9	0.1063	0.7616	1.1325	0.078*
C10	0.0106 (4)	0.8570 (3)	1.16626 (18)	0.0691 (12)
H10	−0.0484	0.8268	1.1888	0.083*
C11	0.0061 (4)	0.9391 (4)	1.16727 (18)	0.0723 (12)
H11	−0.0553	0.9651	1.1913	0.087*
C12	0.0909 (4)	0.9851 (3)	1.13328 (16)	0.0579 (10)
H12	0.0860	1.0417	1.1343	0.070*
C13	0.2164 (3)	1.10211 (19)	1.04311 (16)	0.0452 (8)
C14	0.2650 (4)	1.1740 (2)	1.06457 (17)	0.0543 (10)
H14	0.3442	1.1741	1.0850	0.065*
C15	0.1981 (5)	1.2473 (2)	1.0564 (2)	0.0730 (14)
H15	0.2329	1.2960	1.0706	0.088*
C16	0.0804 (6)	1.2465 (3)	1.0272 (2)	0.0865 (16)
H16	0.0348	1.2950	1.0216	0.104*
C17	0.0295 (6)	1.1749 (3)	1.0060 (3)	0.110 (2)
H17	−0.0508	1.1744	0.9865	0.132*
C18	0.0985 (5)	1.1035 (3)	1.0139 (2)	0.0856 (16)
H18	0.0642	1.0550	0.9990	0.103*
C19	0.3278 (3)	1.07665 (19)	0.84849 (13)	0.0404 (8)
C20	0.3033 (5)	1.1388 (2)	0.88831 (19)	0.0784 (15)
H20	0.3386	1.1364	0.9266	0.094*
C21	0.2265 (6)	1.2051 (3)	0.8721 (2)	0.0907 (17)
H21	0.2141	1.2477	0.8989	0.109*
C22	0.1697 (5)	1.2080 (3)	0.8176 (2)	0.0698 (12)
H22	0.1157	1.2513	0.8071	0.084*
C23	0.1932 (5)	1.1460 (3)	0.7780 (2)	0.0815 (14)
H23	0.1552	1.1474	0.7403	0.098*
C24	0.2720 (4)	1.0819 (3)	0.79331 (18)	0.0649 (11)
H24	0.2877	1.0410	0.7654	0.078*
C25	0.4252 (3)	0.91805 (18)	0.81294 (14)	0.0382 (7)
C26	0.3092 (4)	0.8834 (3)	0.79486 (16)	0.0606 (11)
H26	0.2322	0.8961	0.8149	0.073*
C27	0.3067 (5)	0.8294 (3)	0.74663 (18)	0.0715 (13)
H27	0.2274	0.8086	0.7333	0.086*
C28	0.4188 (5)	0.8070 (2)	0.71913 (18)	0.0670 (12)
H28	0.4168	0.7706	0.6873	0.080*
C29	0.5353 (5)	0.8384 (2)	0.73845 (19)	0.0668 (12)
H29	0.6127	0.8224	0.7202	0.080*
C30	0.5385 (4)	0.8940 (2)	0.78519 (17)	0.0531 (9)
H30	0.6181	0.9152	0.7978	0.064*
C31	0.5944 (3)	1.0287 (2)	0.87255 (14)	0.0384 (7)
C32	0.6363 (4)	1.0808 (2)	0.82716 (16)	0.0479 (8)
H32	0.5764	1.1023	0.8002	0.057*
C33	0.7671 (4)	1.1001 (2)	0.82252 (19)	0.0617 (11)
H33	0.7956	1.1348	0.7923	0.074*
C34	0.8556 (4)	1.0682 (3)	0.8627 (2)	0.0643 (11)
H34	0.9441	1.0799	0.8588	0.077*
C35	0.8137 (4)	1.0195 (2)	0.9080 (2)	0.0603 (10)
H35	0.8735	0.9990	0.9355	0.072*
C36	0.6832 (3)	1.0004 (2)	0.91342 (16)	0.0472 (8)
H36	0.6552	0.9680	0.9450	0.057*
C37	0.3795 (3)	0.73556 (19)	0.96862 (15)	0.0396 (7)
C38	0.2396 (4)	0.6494 (2)	0.93112 (17)	0.0514 (9)
H38	0.1677	0.6295	0.9104	0.062*
N4	1.0664 (6)	0.7141 (3)	0.8189 (3)	0.1146 (18)
C39	0.8865 (6)	0.8191 (4)	0.8394 (3)	0.122 (2)
H39A	0.8616	0.8164	0.8808	0.183*
H39B	0.8121	0.8074	0.8148	0.183*
H39C	0.9183	0.8728	0.8305	0.183*
C40	0.9877 (6)	0.7604 (4)	0.8278 (2)	0.0798 (15)
H3A	0.219 (4)	0.767 (2)	0.926 (2)	0.096*
H1A	0.477 (3)	0.646 (3)	1.001 (2)	0.096*

	U11	U22	U33	U12	U13	U23
Cu1	0.0398 (2)	0.0367 (2)	0.03486 (19)	−0.00132 (17)	0.00169 (18)	0.00165 (17)
Cl1	0.0320 (4)	0.0448 (4)	0.0499 (5)	−0.0026 (3)	−0.0016 (4)	0.0037 (4)
S1	0.0455 (5)	0.0383 (5)	0.0747 (6)	0.0050 (4)	−0.0170 (5)	−0.0032 (5)
P1	0.0398 (4)	0.0322 (4)	0.0362 (4)	−0.0018 (3)	−0.0010 (3)	−0.0013 (3)
P2	0.0344 (4)	0.0397 (5)	0.0322 (4)	−0.0029 (4)	−0.0011 (3)	0.0033 (4)
N1	0.0458 (17)	0.0364 (16)	0.0577 (19)	0.0051 (14)	−0.0041 (14)	0.0052 (14)
N2	0.0525 (17)	0.0423 (16)	0.0651 (19)	0.0000 (15)	0.0029 (17)	0.0033 (16)
N3	0.0385 (16)	0.0387 (16)	0.0549 (18)	0.0053 (13)	−0.0063 (14)	0.0018 (14)
C1	0.047 (2)	0.0366 (18)	0.051 (2)	−0.0024 (16)	−0.0093 (17)	−0.0040 (15)
C2	0.048 (2)	0.059 (3)	0.077 (3)	−0.0066 (18)	−0.001 (2)	−0.018 (2)
C3	0.046 (2)	0.075 (3)	0.134 (5)	0.000 (2)	−0.005 (3)	−0.029 (3)
C4	0.080 (4)	0.087 (4)	0.119 (5)	0.008 (3)	−0.055 (4)	−0.029 (3)
C5	0.104 (5)	0.156 (6)	0.081 (4)	−0.033 (4)	−0.051 (4)	0.010 (4)
C6	0.071 (3)	0.125 (4)	0.056 (3)	−0.022 (3)	−0.015 (2)	0.004 (3)
C7	0.0415 (19)	0.0448 (19)	0.0340 (16)	−0.0072 (16)	−0.0025 (14)	0.0009 (15)
C8	0.061 (2)	0.047 (2)	0.0440 (19)	−0.0071 (19)	0.0028 (18)	−0.0026 (17)
C9	0.082 (3)	0.059 (2)	0.055 (2)	−0.019 (2)	−0.009 (2)	0.011 (2)
C10	0.065 (3)	0.091 (4)	0.051 (2)	−0.025 (3)	0.004 (2)	0.015 (2)
C11	0.063 (3)	0.102 (4)	0.053 (2)	−0.002 (3)	0.019 (2)	0.001 (3)
C12	0.057 (2)	0.065 (2)	0.052 (2)	−0.005 (2)	0.0072 (19)	−0.003 (2)
C13	0.054 (2)	0.0348 (17)	0.0466 (19)	0.0038 (16)	0.0024 (18)	0.0010 (16)
C14	0.065 (2)	0.039 (2)	0.059 (2)	−0.0034 (18)	0.007 (2)	−0.0043 (17)
C15	0.100 (4)	0.037 (2)	0.082 (3)	0.000 (2)	0.021 (3)	−0.006 (2)
C16	0.104 (4)	0.051 (3)	0.105 (4)	0.033 (3)	0.007 (4)	0.000 (3)
C17	0.093 (4)	0.082 (4)	0.157 (6)	0.039 (3)	−0.049 (4)	−0.013 (4)
C18	0.087 (3)	0.056 (3)	0.114 (4)	0.017 (2)	−0.049 (3)	−0.016 (3)
C19	0.0381 (18)	0.0442 (19)	0.0390 (17)	−0.0013 (15)	0.0002 (15)	0.0077 (14)
C20	0.130 (5)	0.049 (2)	0.056 (2)	0.018 (3)	−0.023 (3)	−0.005 (2)
C21	0.153 (5)	0.046 (2)	0.073 (3)	0.027 (3)	0.009 (3)	−0.001 (2)
C22	0.070 (3)	0.059 (3)	0.080 (3)	0.017 (2)	0.009 (3)	0.027 (2)
C23	0.085 (3)	0.086 (3)	0.073 (3)	0.019 (3)	−0.030 (3)	0.012 (3)
C24	0.076 (3)	0.064 (3)	0.055 (2)	0.020 (2)	−0.014 (2)	−0.0043 (19)
C25	0.0477 (19)	0.0370 (18)	0.0298 (16)	−0.0022 (15)	−0.0008 (15)	0.0044 (13)
C26	0.063 (3)	0.073 (3)	0.046 (2)	−0.017 (2)	0.0061 (19)	−0.013 (2)
C27	0.083 (3)	0.075 (3)	0.056 (3)	−0.026 (3)	−0.008 (2)	−0.014 (2)
C28	0.108 (4)	0.045 (2)	0.048 (2)	−0.002 (2)	0.000 (2)	−0.0103 (18)
C29	0.081 (3)	0.051 (2)	0.069 (3)	0.009 (2)	0.009 (2)	−0.015 (2)
C30	0.055 (2)	0.046 (2)	0.058 (2)	0.0056 (18)	0.0003 (19)	−0.0058 (18)
C31	0.0368 (18)	0.0416 (18)	0.0369 (17)	−0.0023 (14)	0.0049 (15)	−0.0008 (14)
C32	0.046 (2)	0.049 (2)	0.0481 (19)	−0.0044 (17)	0.0041 (17)	0.0025 (16)
C33	0.062 (3)	0.057 (2)	0.065 (2)	−0.016 (2)	0.019 (2)	0.001 (2)
C34	0.040 (2)	0.061 (2)	0.092 (3)	−0.007 (2)	0.012 (2)	−0.009 (2)
C35	0.047 (2)	0.053 (2)	0.081 (3)	0.0003 (19)	−0.012 (2)	0.003 (2)
C36	0.0380 (19)	0.049 (2)	0.055 (2)	−0.0002 (16)	0.0014 (16)	0.0043 (17)
C37	0.0353 (17)	0.0430 (18)	0.0405 (18)	0.0076 (14)	0.0042 (15)	0.0044 (15)
C38	0.042 (2)	0.047 (2)	0.065 (2)	−0.0008 (17)	0.0008 (19)	−0.0066 (18)
N4	0.108 (4)	0.109 (4)	0.127 (4)	0.007 (3)	−0.037 (4)	−0.021 (4)
C39	0.098 (5)	0.127 (5)	0.141 (5)	0.003 (4)	−0.040 (4)	−0.037 (5)
C40	0.080 (4)	0.081 (4)	0.078 (3)	−0.023 (3)	−0.029 (3)	−0.003 (3)

Cu1—P1	2.2802 (9)	C15—H15	0.9300
Cu1—P2	2.2824 (9)	C16—C17	1.370 (7)
Cu1—S1	2.3582 (9)	C16—H16	0.9300
Cu1—Cl1	2.4035 (9)	C17—C18	1.378 (6)
S1—C37	1.700 (3)	C17—H17	0.9300
P1—C13	1.831 (3)	C18—H18	0.9300
P1—C7	1.834 (3)	C19—C24	1.363 (5)
P1—C1	1.834 (4)	C19—C20	1.377 (5)
P2—C19	1.833 (3)	C20—C21	1.390 (6)
P2—C25	1.841 (3)	C20—H20	0.9300
P2—C31	1.841 (3)	C21—C22	1.352 (7)
N1—C37	1.326 (4)	C21—H21	0.9300
N1—N2	1.364 (4)	C22—C23	1.369 (6)
N1—H1A	0.844 (19)	C22—H22	0.9300
N2—C38	1.289 (5)	C23—C24	1.368 (6)
N3—C37	1.343 (4)	C23—H23	0.9300
N3—C38	1.361 (4)	C24—H24	0.9300
N3—H3A	0.835 (19)	C25—C30	1.372 (5)
C1—C6	1.361 (6)	C25—C26	1.377 (5)
C1—C2	1.362 (5)	C26—C27	1.397 (5)
C2—C3	1.393 (6)	C26—H26	0.9300
C2—H2	0.9300	C27—C28	1.352 (6)
C3—C4	1.336 (7)	C27—H27	0.9300
C3—H3	0.9300	C28—C29	1.369 (6)
C4—C5	1.355 (8)	C28—H28	0.9300
C4—H4	0.9300	C29—C30	1.388 (5)
C5—C6	1.379 (7)	C29—H29	0.9300
C5—H5	0.9300	C30—H30	0.9300
C6—H6	0.9300	C31—C36	1.370 (5)
C7—C12	1.386 (5)	C31—C32	1.394 (5)
C7—C8	1.388 (5)	C32—C33	1.380 (5)
C8—C9	1.384 (5)	C32—H32	0.9300
C8—H8	0.9300	C33—C34	1.379 (6)
C9—C10	1.362 (6)	C33—H33	0.9300
C9—H9	0.9300	C34—C35	1.360 (6)
C10—C11	1.347 (7)	C34—H34	0.9300
C10—H10	0.9300	C35—C36	1.378 (5)
C11—C12	1.379 (6)	C35—H35	0.9300
C11—H11	0.9300	C36—H36	0.9300
C12—H12	0.9300	C38—H38	0.9300
C13—C14	1.368 (5)	N4—C40	1.125 (7)
C13—C18	1.373 (6)	C39—C40	1.438 (8)
C14—C15	1.395 (6)	C39—H39A	0.9600
C14—H14	0.9300	C39—H39B	0.9600
C15—C16	1.371 (7)	C39—H39C	0.9600
P1—Cu1—P2	128.63 (3)	C16—C17—C18	119.3 (5)
P1—Cu1—S1	106.88 (4)	C16—C17—H17	120.3
P2—Cu1—S1	109.27 (4)	C18—C17—H17	120.3
P1—Cu1—Cl1	100.54 (3)	C13—C18—C17	121.6 (5)
P2—Cu1—Cl1	99.26 (3)	C13—C18—H18	119.2
S1—Cu1—Cl1	110.93 (3)	C17—C18—H18	119.2
C37—S1—Cu1	109.39 (11)	C24—C19—C20	117.5 (3)
C13—P1—C7	101.60 (16)	C24—C19—P2	125.3 (3)
C13—P1—C1	104.29 (16)	C20—C19—P2	117.0 (3)
C7—P1—C1	103.35 (15)	C19—C20—C21	120.9 (4)
C13—P1—Cu1	116.40 (12)	C19—C20—H20	119.5
C7—P1—Cu1	113.32 (11)	C21—C20—H20	119.5
C1—P1—Cu1	116.05 (12)	C22—C21—C20	120.4 (4)
C19—P2—C25	104.12 (14)	C22—C21—H21	119.8
C19—P2—C31	103.71 (15)	C20—C21—H21	119.8
C25—P2—C31	100.96 (15)	C21—C22—C23	118.7 (4)
C19—P2—Cu1	112.43 (10)	C21—C22—H22	120.6
C25—P2—Cu1	113.78 (10)	C23—C22—H22	120.6
C31—P2—Cu1	120.00 (11)	C24—C23—C22	120.9 (4)
C37—N1—N2	113.0 (3)	C24—C23—H23	119.6
C37—N1—H1A	122 (4)	C22—C23—H23	119.6
N2—N1—H1A	124 (4)	C19—C24—C23	121.5 (4)
C38—N2—N1	103.2 (3)	C19—C24—H24	119.3
C37—N3—C38	107.3 (3)	C23—C24—H24	119.3
C37—N3—H3A	128 (4)	C30—C25—C26	118.5 (3)
C38—N3—H3A	122 (4)	C30—C25—P2	122.0 (3)
C6—C1—C2	118.7 (4)	C26—C25—P2	119.4 (3)
C6—C1—P1	122.4 (3)	C25—C26—C27	120.3 (4)
C2—C1—P1	118.9 (3)	C25—C26—H26	119.9
C1—C2—C3	119.9 (4)	C27—C26—H26	119.9
C1—C2—H2	120.1	C28—C27—C26	120.5 (4)
C3—C2—H2	120.1	C28—C27—H27	119.7
C4—C3—C2	120.6 (5)	C26—C27—H27	119.7
C4—C3—H3	119.7	C27—C28—C29	119.6 (4)
C2—C3—H3	119.7	C27—C28—H28	120.2
C3—C4—C5	120.0 (5)	C29—C28—H28	120.2
C3—C4—H4	120.0	C28—C29—C30	120.4 (4)
C5—C4—H4	120.0	C28—C29—H29	119.8
C4—C5—C6	119.9 (5)	C30—C29—H29	119.8
C4—C5—H5	120.1	C25—C30—C29	120.6 (4)
C6—C5—H5	120.1	C25—C30—H30	119.7
C1—C6—C5	120.9 (5)	C29—C30—H30	119.7
C1—C6—H6	119.5	C36—C31—C32	119.3 (3)
C5—C6—H6	119.5	C36—C31—P2	118.8 (3)
C12—C7—C8	118.4 (3)	C32—C31—P2	121.7 (3)
C12—C7—P1	123.1 (3)	C33—C32—C31	119.6 (4)
C8—C7—P1	118.5 (3)	C33—C32—H32	120.2
C9—C8—C7	120.0 (4)	C31—C32—H32	120.2
C9—C8—H8	120.0	C34—C33—C32	120.0 (4)
C7—C8—H8	120.0	C34—C33—H33	120.0
C10—C9—C8	120.5 (4)	C32—C33—H33	120.0
C10—C9—H9	119.8	C35—C34—C33	120.2 (4)
C8—C9—H9	119.8	C35—C34—H34	119.9
C11—C10—C9	120.0 (4)	C33—C34—H34	119.9
C11—C10—H10	120.0	C34—C35—C36	120.3 (4)
C9—C10—H10	120.0	C34—C35—H35	119.9
C10—C11—C12	121.1 (4)	C36—C35—H35	119.9
C10—C11—H11	119.5	C31—C36—C35	120.5 (4)
C12—C11—H11	119.5	C31—C36—H36	119.7
C11—C12—C7	120.1 (4)	C35—C36—H36	119.7
C11—C12—H12	119.9	N1—C37—N3	104.5 (3)
C7—C12—H12	119.9	N1—C37—S1	126.5 (3)
C14—C13—C18	118.2 (3)	N3—C37—S1	129.0 (3)
C14—C13—P1	124.7 (3)	N2—C38—N3	111.9 (3)
C18—C13—P1	117.1 (3)	N2—C38—H38	124.1
C13—C14—C15	121.3 (4)	N3—C38—H38	124.1
C13—C14—H14	119.4	C40—C39—H39A	109.5
C15—C14—H14	119.4	C40—C39—H39B	109.5
C16—C15—C14	119.0 (4)	H39A—C39—H39B	109.5
C16—C15—H15	120.5	C40—C39—H39C	109.5
C14—C15—H15	120.5	H39A—C39—H39C	109.5
C17—C16—C15	120.5 (4)	H39B—C39—H39C	109.5
C17—C16—H16	119.7	N4—C40—C39	179.7 (8)
C15—C16—H16	119.7
P1—Cu1—S1—C37	116.24 (13)	P1—C13—C14—C15	178.5 (3)
P2—Cu1—S1—C37	−100.90 (13)	C13—C14—C15—C16	1.1 (7)
Cl1—Cu1—S1—C37	7.53 (13)	C14—C15—C16—C17	−0.3 (8)
P2—Cu1—P1—C13	41.73 (14)	C15—C16—C17—C18	−0.6 (10)
S1—Cu1—P1—C13	174.88 (13)	C14—C13—C18—C17	−0.1 (7)
Cl1—Cu1—P1—C13	−69.26 (13)	P1—C13—C18—C17	−179.5 (5)
P2—Cu1—P1—C7	159.03 (12)	C16—C17—C18—C13	0.8 (10)
S1—Cu1—P1—C7	−67.83 (12)	C25—P2—C19—C24	−0.6 (4)
Cl1—Cu1—P1—C7	48.03 (12)	C31—P2—C19—C24	104.7 (3)
P2—Cu1—P1—C1	−81.59 (13)	Cu1—P2—C19—C24	−124.2 (3)
S1—Cu1—P1—C1	51.56 (13)	C25—P2—C19—C20	175.6 (3)
Cl1—Cu1—P1—C1	167.42 (13)	C31—P2—C19—C20	−79.2 (4)
P1—Cu1—P2—C19	−53.12 (13)	Cu1—P2—C19—C20	51.9 (4)
S1—Cu1—P2—C19	174.57 (12)	C24—C19—C20—C21	−1.3 (7)
Cl1—Cu1—P2—C19	58.44 (12)	P2—C19—C20—C21	−177.8 (4)
P1—Cu1—P2—C25	−171.18 (12)	C19—C20—C21—C22	2.9 (8)
S1—Cu1—P2—C25	56.52 (12)	C20—C21—C22—C23	−2.4 (8)
Cl1—Cu1—P2—C25	−59.61 (12)	C21—C22—C23—C24	0.4 (8)
P1—Cu1—P2—C31	69.18 (13)	C20—C19—C24—C23	−0.7 (7)
S1—Cu1—P2—C31	−63.12 (13)	P2—C19—C24—C23	175.5 (4)
Cl1—Cu1—P2—C31	−179.25 (13)	C22—C23—C24—C19	1.2 (8)
C37—N1—N2—C38	−1.1 (4)	C19—P2—C25—C30	119.2 (3)
C13—P1—C1—C6	88.1 (4)	C31—P2—C25—C30	11.9 (3)
C7—P1—C1—C6	−17.8 (4)	Cu1—P2—C25—C30	−118.1 (3)
Cu1—P1—C1—C6	−142.5 (4)	C19—P2—C25—C26	−64.1 (3)
C13—P1—C1—C2	−93.5 (3)	C31—P2—C25—C26	−171.4 (3)
C7—P1—C1—C2	160.6 (3)	Cu1—P2—C25—C26	58.6 (3)
Cu1—P1—C1—C2	36.0 (3)	C30—C25—C26—C27	−4.3 (6)
C6—C1—C2—C3	−0.3 (6)	P2—C25—C26—C27	178.9 (3)
P1—C1—C2—C3	−178.8 (3)	C25—C26—C27—C28	3.5 (7)
C1—C2—C3—C4	2.1 (7)	C26—C27—C28—C29	−0.7 (7)
C2—C3—C4—C5	−3.1 (8)	C27—C28—C29—C30	−1.2 (7)
C3—C4—C5—C6	2.2 (10)	C26—C25—C30—C29	2.4 (5)
C2—C1—C6—C5	−0.5 (8)	P2—C25—C30—C29	179.2 (3)
P1—C1—C6—C5	177.9 (5)	C28—C29—C30—C25	0.4 (6)
C4—C5—C6—C1	−0.4 (10)	C19—P2—C31—C36	149.0 (3)
C13—P1—C7—C12	−19.7 (3)	C25—P2—C31—C36	−103.3 (3)
C1—P1—C7—C12	88.2 (3)	Cu1—P2—C31—C36	22.6 (3)
Cu1—P1—C7—C12	−145.4 (3)	C19—P2—C31—C32	−35.7 (3)
C13—P1—C7—C8	158.7 (3)	C25—P2—C31—C32	71.9 (3)
C1—P1—C7—C8	−93.3 (3)	Cu1—P2—C31—C32	−162.2 (2)
Cu1—P1—C7—C8	33.1 (3)	C36—C31—C32—C33	2.8 (5)
C12—C7—C8—C9	−0.9 (5)	P2—C31—C32—C33	−172.4 (3)
P1—C7—C8—C9	−179.5 (3)	C31—C32—C33—C34	−0.1 (6)
C7—C8—C9—C10	1.8 (6)	C32—C33—C34—C35	−2.0 (6)
C8—C9—C10—C11	−1.9 (7)	C33—C34—C35—C36	1.4 (6)
C9—C10—C11—C12	1.3 (7)	C32—C31—C36—C35	−3.4 (5)
C10—C11—C12—C7	−0.5 (6)	P2—C31—C36—C35	171.9 (3)
C8—C7—C12—C11	0.3 (5)	C34—C35—C36—C31	1.3 (6)
P1—C7—C12—C11	178.8 (3)	N2—N1—C37—N3	0.4 (4)
C7—P1—C13—C14	115.5 (3)	N2—N1—C37—S1	−178.8 (2)
C1—P1—C13—C14	8.3 (4)	C38—N3—C37—N1	0.4 (4)
Cu1—P1—C13—C14	−120.9 (3)	C38—N3—C37—S1	179.5 (3)
C7—P1—C13—C18	−65.0 (4)	Cu1—S1—C37—N1	−168.9 (3)
C1—P1—C13—C18	−172.2 (3)	Cu1—S1—C37—N3	12.1 (3)
Cu1—P1—C13—C18	58.6 (4)	N1—N2—C38—N3	1.3 (4)
C18—C13—C14—C15	−0.9 (6)	C37—N3—C38—N2	−1.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···Cl1	0.84 (2)	2.41 (3)	3.183 (3)	155 (5)
N1—H1A···Cl1i	0.84 (2)	2.34 (2)	3.154 (3)	163 (5)
C15—H15···Cg7ii	0.93	2.88	3.749 (4)	155

Table 1

Selected bond lengths (Å)

Cu1—P1	2.2802 (9)
Cu1—P2	2.2824 (9)
Cu1—S1	2.3582 (9)
Cu1—Cl1	2.4035 (9)

Table 2

Hydrogen-bond geometry (Å, °)

Cg7 is the centroid of the C31–C36 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯Cl1	0.84 (2)	2.41 (3)	3.183 (3)	155 (5)
N1—H1A⋯Cl1i	0.84 (2)	2.34 (2)	3.154 (3)	163 (5)
C15—H15⋯Cg7ii	0.93	2.88	3.749 (4)	155

Symmetry codes: (i) ; (ii) .