Chlorido(1-pyrrolidinecarbodithio­ato-κ²S,S′)(triphenyl­phosphine-κP)nickel(II) chloro­form hemisolvate

In the crystal structure of the title complex, [Ni{S₂CN(CH₂)₄}Cl(C₁₈H₁₅P)]·0.5CHCl₃, the Ni atom is coordinated by a bidentate dithio­carbamate, one chloride and triphenyl­phosphine in a square-planar arrangement. The chloro­form solvent mol­ecule inter­acts with the complex through a weak C—H...S hydrogen bond. The solvent molecule is disordered equally over two inversion-related sites.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.058
• wR factor = 0.119
• Data-to-parameter ratio = 21.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       2000 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.52 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C3
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C3     -   C4     ...       1.43 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  S2      ..       3.34 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  S1     ..  C37     ..       3.28 Ang.

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C47 H47 Cl5 N2 Ni2 P2 S4
            Atom count from _chemical_formula_moiety:C23.5 H23.5 Cl2.5 N1 Ni1 P1
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          6

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The 1-Pyrrolidinecarbodithioato-group is one of the most frequently used sulfur donor ligands and structural data for nearly 100 complexes are stored in the Cambridge Structural Database (CSD-2007, Allen 2002). Recently, we reported the synthesis of the tris(1-pyrrolidinylcarbodithioato-S,S')-cobalt(III) complex obtained as chloroform disolvate [Co(S₂CN(CH₂)₄)₃] × 2CHCl₃ (I) (Kropidłowska et al. 2007). The most notable feature of its structure was the apparent interaction of CHCl₃ with a sulfur atom from the ligand (Cl₃C—H···S).

In the present paper we describe the structure of a nickel(II) complex - chlorido(1-pyrrolidinecarbodithioato-S,S')(triphenylphosphine)nickel(II) (I) which was isolated as a chloroform hemisolvate. It can be regarded as a dithiocarbamate complex with a four-coordinated metal(II) ion within a square planar, heterogeneous [NiClS₂P] coordination sphere. There are only small deviations from planarity, not exceeding 0.07 Å. The molecular structure of (I) with atom numbering scheme is shown in Fig.1. The solvating chloroform molecule is equally disordered over two sites related by an inversion center. Again, the interaction of CHCl₃ with the complex seems to be present (Cl₃C—H···S distance equals 2.4 Å) and one can suppose that weak C—H···S hydrogen bond is formed, somewhat reinforcing the structure (Fig. 2). Short Cl1···S2 (3.341 Å) as well as some short C_arH···Cl (ca 2.93 Å) contacts may be also noticed.

The structures of two similar hemisolvated nickel(II) complexes have been reported previously: homologous bromido(1-pyrrolidinylcarbodithioato-S,S')(triphenylphosphine)nickel(II) (refcode TIZJAN, Pastorek et al., 1996) and closely related thiazolidinedithiocarbamate with nickel(II) bonded to triphenylphosphine and chloride ligands (refcode GOZBUS, Pastorek et al., 1999). However, in both cases, the Cl₃C—H···S distance is greater than 2.7 Å and even speculations about the existence of any weak hydrogen bond seem doubtful.

Related literature

For related literature, see: Allen (2002); Garton et al. (1963); Kropidłowska et al. (2007); Pastorek et al. (1996, 1999); Venanzi (1958).

S2. Experimental

Nickel chloride, NiCl₂ × 6H₂O (0.594 g, 0.0025 mol, purchased from POCh) was dissolved in 50 ml of methanol/water (10/1, v/v) and this solution was added dropwise to the ammonium salt of pyrrolidinecarbodithioic acid C₄H₈NCS₂NH₄ (0.82 g, 0.005 mol, Fluka) dissolved in methanol/water. This mixture was stirred vigorously under argon atmosphere for app. 20 minutes, then filtered and the filtrate left for crystallization at 5°C. After a week the green crystalline product Ni(S₂CNC₄H₈)₂ was collected. It was further dissolved (0.199 g, 0.00057 mol) in 10 ml of chloroform and mixed with solution of equimolar amount of NiCl₂(PPh₃)₂ (0.37 g) prepared as described in the literature (Venanzi, 1958; Garton et al. 1963). The mixture which turned into deep violet color, was stirred for 10 minutes and then filtered. To this solution 10 ml of Et₂O was added. After dwo days purple crystals were collected and washed with several portions of ether.

S3. Refinement

All H atoms were positioned geometrically and treated as riding with U_iso(H) values of 1.5U_eq of the C joined directly the H or 1.2U_eq of the C joined H for aromatic. The solvated molecule of CHCl₃ is statistically disordered (occupation factor of 1/2).

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. Molecular structure and atom-numbering scheme for (I) with displacement ellipsoids drawn at 50% probability level. The chloroform molecule is disordered - only one set is shown. Broken line denotes the assumed C—H···S hydrogen bond. Color codes: Ni pink-red, N blue, S yellow, Cl green, P orange, C gray. H atoms are shown as small white rings of arbitrary size.
	Fig. 2. Schematic drawing of the crystal packing of molecules of (I) showing the C—H···S interactions. Besides chloroform, all other H atoms have been omitted for clarity.

Chlorido(1-pyrrolidinecarbodithioato-κ²S,S')(triphenylphosphine- κP)nickel(II) chloroform hemisolvate

Crystal data

[Ni(C5H8NS2)Cl(C18H15P)]·0.5CHCl3	Z = 1
Mr = 1124.72	F(000) = 578
Triclinic, P1	Dx = 1.482 Mg m^−3 Dm = 1.48 Mg m^−3 Dm measured by floatation
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.713 (2) Å	Cell parameters from 876 reflections
b = 10.076 (2) Å	θ = 2.7–28.0°
c = 14.509 (3) Å	µ = 1.28 mm^−1
α = 90.37 (2)°	T = 295 K
β = 91.21 (2)°	Paralellepiped, purple
γ = 117.39 (2)°	0.25 × 0.22 × 0.18 mm
V = 1260.3 (5) Å^3

Data collection

Kuma KM-4 with CCD area detector diffractometer	6060 independent reflections
Radiation source: fine-focus sealed tube	3417 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
Detector resolution: 1024x1024 with blocks 2x2 pixels mm^-1	θmax = 28.0°, θmin = 2.7°
ω scans	h = −12→12
Absorption correction: analytical (face-indexed) (SHELXTL; Sheldrick, 1990)	k = −13→10
Tmin = 0.741, Tmax = 0.799	l = −18→19
16395 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0351P)^2] where P = (Fo^2 + 2Fc^2)/3
6060 reflections	(Δ/σ)max = 0.006
286 parameters	Δρmax = 0.48 e Å^−3
6 restraints	Δρmin = −0.51 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl4	0.11616 (10)	0.13720 (11)	0.28665 (7)	0.0926 (4)
Ni	0.36198 (4)	0.29476 (4)	0.28472 (3)	0.05004 (11)
S1	0.33333 (9)	0.44183 (9)	0.38849 (6)	0.0619 (3)
S2	0.59132 (9)	0.48808 (9)	0.28702 (6)	0.0633 (3)
C1	0.5177 (3)	0.5698 (3)	0.36361 (19)	0.0538 (9)
N1	0.5905 (3)	0.7057 (3)	0.39337 (17)	0.0562 (8)
C2	0.5209 (4)	0.7713 (3)	0.4563 (2)	0.0702 (11)
H2A	0.4920	0.7164	0.5133	0.105*
H2B	0.4297	0.7717	0.4280	0.105*
C3	0.6481 (4)	0.9290 (4)	0.4737 (3)	0.1076 (17)
H3A	0.6210	1.0002	0.4442	0.161*
H3B	0.6629	0.9515	0.5393	0.161*
C4	0.7866 (5)	0.9375 (5)	0.4359 (4)	0.109 (2)
H4A	0.8544	0.9355	0.4853	0.163*
H4B	0.8408	1.0309	0.4037	0.163*
C5	0.7491 (4)	0.8119 (4)	0.3719 (3)	0.0829 (13)
H5A	0.7556	0.8435	0.3084	0.124*
H5B	0.8189	0.7684	0.3818	0.124*
P1	0.41303 (8)	0.16922 (8)	0.17730 (5)	0.0439 (2)
C11	0.3175 (3)	0.1762 (3)	0.07035 (19)	0.0436 (8)
C12	0.3251 (3)	0.3130 (3)	0.0462 (2)	0.0630 (10)
H12	0.3753	0.3959	0.0853	0.076*
C13	0.2575 (4)	0.3253 (4)	−0.0365 (2)	0.0738 (11)
H13	0.2654	0.4174	−0.0533	0.089*
C14	0.1803 (3)	0.2046 (4)	−0.0929 (2)	0.0673 (11)
H14	0.1322	0.2133	−0.1470	0.081*
C15	0.1729 (3)	0.0681 (3)	−0.0701 (2)	0.0623 (11)
H15	0.1223	−0.0143	−0.1096	0.075*
C16	0.2407 (3)	0.0552 (3)	0.0110 (2)	0.0588 (10)
H16	0.2348	−0.0367	0.0262	0.071*
C21	0.3574 (3)	−0.0297 (3)	0.1936 (2)	0.0686 (9)
C22	0.2114 (4)	−0.1258 (4)	0.2214 (3)	0.0904 (14)
H22	0.1417	−0.0890	0.2340	0.109*
C23	0.1652 (5)	−0.2791 (4)	0.2311 (3)	0.0955 (17)
H23	0.0650	−0.3442	0.2483	0.127*
C24	0.2698 (4)	−0.3304 (4)	0.2147 (3)	0.0820 (13)
H24	0.2417	−0.4311	0.2227	0.098*
C25	0.4138 (4)	−0.2375 (3)	0.1870 (2)	0.0745 (11)
H25	0.4831	−0.2748	0.1746	0.089*
C26	0.4585 (4)	−0.0872 (3)	0.1769 (2)	0.0614 (10)
H26	0.5586	−0.0239	0.1586	0.074*
C31	0.6157 (3)	0.2440 (3)	0.14972 (19)	0.0426 (8)
C32	0.7206 (3)	0.2612 (3)	0.2213 (2)	0.0549 (9)
H32	0.6872	0.2443	0.2817	0.066*
C33	0.8749 (3)	0.3035 (3)	0.2029 (3)	0.0695 (11)
H33	0.9440	0.3112	0.2505	0.083*
C34	0.9246 (4)	0.3338 (3)	0.1144 (2)	0.0686 (11)
H34	1.0283	0.3636	0.1026	0.082*
C35	0.8257 (4)	0.3211 (3)	0.0435 (2)	0.0664 (11)
H35	0.8612	0.3434	−0.0163	0.080*
C36	0.67116 (16)	0.27453 (16)	0.06166 (10)	0.0518 (9)
H36	0.6026	0.2635	0.0130	0.062*
Cl1	0.12808 (9)	0.52365 (14)	0.58149 (7)	0.1235 (10)	0.50
Cl2	−0.11177 (9)	0.34498 (14)	0.45802 (7)	0.1810 (16)	0.50
Cl3	0.02592 (9)	0.65936 (14)	0.44795 (7)	0.1659 (18)	0.50
C37	0.05796 (9)	0.50814 (14)	0.46966 (7)	0.143 (5)	0.50
H37	0.1324	0.5067	0.4278	0.207*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl4	0.0502 (5)	0.1054 (7)	0.1103 (8)	0.0253 (5)	0.0148 (5)	−0.0215 (6)
Ni	0.04922 (18)	0.0602 (2)	0.0474 (2)	0.03066 (15)	0.00490 (18)	0.00314 (17)
S1	0.0667 (4)	0.0665 (5)	0.0618 (5)	0.0378 (4)	0.0182 (4)	0.0040 (4)
S2	0.0594 (4)	0.0589 (4)	0.0717 (6)	0.0267 (4)	0.0177 (4)	−0.0071 (4)
C1	0.0638 (16)	0.0658 (17)	0.0437 (17)	0.0397 (13)	0.0075 (15)	0.0105 (14)
N1	0.0593 (13)	0.0519 (13)	0.0588 (16)	0.0264 (11)	0.0103 (13)	−0.0072 (12)
C2	0.089 (2)	0.0697 (18)	0.066 (2)	0.0492 (15)	0.0069 (19)	−0.0092 (17)
C3	0.099 (3)	0.077 (2)	0.137 (4)	0.033 (2)	0.009 (3)	−0.040 (3)
C4	0.097 (3)	0.088 (3)	0.100 (5)	0.021 (3)	0.011 (4)	−0.041 (3)
C5	0.074 (2)	0.069 (2)	0.093 (3)	0.0221 (19)	0.018 (2)	−0.015 (2)
P1	0.0406 (4)	0.0461 (4)	0.0462 (5)	0.0211 (3)	0.0014 (4)	0.0024 (4)
C11	0.0477 (13)	0.0398 (13)	0.0473 (17)	0.0234 (11)	0.0050 (14)	0.0080 (13)
C12	0.0791 (19)	0.0551 (17)	0.061 (2)	0.0369 (15)	−0.0110 (18)	−0.0067 (16)
C13	0.092 (2)	0.0659 (19)	0.073 (2)	0.0442 (17)	−0.004 (2)	0.0112 (18)
C14	0.0557 (17)	0.088 (2)	0.060 (2)	0.0352 (16)	−0.0135 (17)	0.0069 (18)
C15	0.0595 (19)	0.0636 (19)	0.0527 (19)	0.0196 (16)	−0.0157 (17)	−0.0104 (16)
C16	0.0646 (18)	0.0550 (17)	0.057 (2)	0.0276 (14)	0.0001 (17)	−0.0002 (15)
C21	0.0743 (15)	0.0629 (15)	0.0697 (18)	0.0135 (12)	−0.0012 (15)	−0.0007 (14)
C22	0.067 (2)	0.065 (2)	0.128 (3)	0.0201 (19)	0.024 (2)	0.017 (2)
C23	0.083 (3)	0.062 (2)	0.118 (4)	0.013 (2)	0.017 (3)	0.020 (3)
C24	0.090 (3)	0.0528 (19)	0.092 (3)	0.0238 (18)	−0.019 (2)	0.0194 (19)
C25	0.0838 (19)	0.0535 (17)	0.100 (3)	0.0443 (14)	−0.022 (2)	0.0027 (18)
C26	0.0631 (19)	0.0474 (17)	0.071 (2)	0.0230 (15)	0.0043 (18)	0.0076 (16)
C31	0.0401 (13)	0.0333 (13)	0.0523 (18)	0.0149 (11)	0.0055 (14)	0.0033 (13)
C32	0.0430 (14)	0.0623 (17)	0.062 (2)	0.0268 (13)	0.0016 (16)	−0.0041 (16)
C33	0.0470 (17)	0.068 (2)	0.090 (3)	0.0244 (15)	−0.0150 (19)	−0.0247 (19)
C34	0.0484 (17)	0.0573 (18)	0.093 (3)	0.0183 (14)	0.0086 (19)	−0.0264 (19)
C35	0.0627 (19)	0.0535 (18)	0.073 (2)	0.0175 (16)	0.0182 (19)	−0.0055 (17)
C36	0.0501 (16)	0.0440 (15)	0.0590 (19)	0.0196 (13)	0.0050 (16)	0.0014 (14)
Cl1	0.0964 (16)	0.181 (2)	0.0792 (15)	0.0526 (16)	−0.0068 (13)	−0.0183 (15)
Cl2	0.125 (2)	0.195 (3)	0.172 (3)	0.033 (2)	−0.032 (2)	−0.089 (2)
Cl3	0.176 (3)	0.165 (3)	0.176 (5)	0.105 (2)	0.013 (3)	0.074 (3)
C37	0.146 (9)	0.103 (6)	0.173 (10)	0.055 (6)	−0.073 (7)	−0.021 (6)

Geometric parameters (Å, º)

Cl4—Ni	2.1763 (11)	C14—H14	0.9300
Ni—S2	2.1820 (11)	C15—C16	1.371 (4)
Ni—P1	2.2045 (10)	C15—H15	0.9300
Ni—S1	2.2155 (11)	C16—H16	0.9300
S1—C1	1.705 (3)	C21—C22	1.368 (4)
S2—C1	1.727 (3)	C21—C26	1.375 (4)
C1—N1	1.285 (3)	C22—C23	1.408 (5)
N1—C5	1.456 (4)	C22—H22	0.9300
N1—C2	1.470 (4)	C23—C24	1.359 (6)
C2—C3	1.518 (4)	C23—H23	0.9300
C2—H2A	0.9700	C24—C25	1.347 (5)
C2—H2B	0.9700	C24—H24	0.9300
C3—C4	1.425 (6)	C25—C26	1.381 (4)
C3—H3A	0.9700	C25—H25	0.9300
C3—H3B	0.9700	C26—H26	0.9300
C4—C5	1.466 (5)	C31—C36	1.378 (3)
C4—H4A	0.9700	C31—C32	1.391 (4)
C4—H4B	0.9700	C32—C33	1.387 (4)
C5—H5A	0.9700	C32—H32	0.9300
C5—H5B	0.9700	C33—C34	1.367 (5)
P1—C31	1.811 (3)	C33—H33	0.9300
P1—C11	1.811 (3)	C34—C35	1.357 (5)
P1—C21	1.839 (3)	C34—H34	0.9300
C11—C16	1.379 (4)	C35—C36	1.385 (3)
C11—C12	1.394 (4)	C35—H35	0.9300
C12—C13	1.390 (4)	C36—H36	0.9300
C12—H12	0.9300	Cl1—C37	1.7244
C13—C14	1.353 (4)	Cl2—C37	1.7146
C13—H13	0.9300	Cl3—C37	1.7193
C14—C15	1.385 (4)	C37—H37	0.9600
Cl4—Ni—S2	167.86 (5)	C12—C13—H13	119.6
Cl4—Ni—P1	94.09 (4)	C13—C14—C15	120.1 (3)
S2—Ni—P1	95.56 (4)	C13—C14—H14	119.9
Cl4—Ni—S1	91.55 (4)	C15—C14—H14	119.9
S2—Ni—S1	78.57 (4)	C16—C15—C14	119.6 (3)
P1—Ni—S1	173.95 (3)	C16—C15—H15	120.2
C1—S1—Ni	86.07 (11)	C14—C15—H15	120.2
C1—S2—Ni	86.62 (10)	C15—C16—C11	121.2 (3)
N1—C1—S1	126.9 (3)	C15—C16—H16	119.4
N1—C1—S2	124.6 (2)	C11—C16—H16	119.4
S1—C1—S2	108.46 (16)	C22—C21—C26	118.0 (3)
C1—N1—C5	125.7 (3)	C22—C21—P1	120.4 (3)
C1—N1—C2	122.5 (2)	C26—C21—P1	121.6 (2)
C5—N1—C2	111.9 (2)	C21—C22—C23	121.2 (4)
N1—C2—C3	103.6 (3)	C21—C22—H22	119.4
N1—C2—H2A	111.0	C23—C22—H22	119.4
C3—C2—H2A	111.0	C24—C23—C22	118.5 (3)
N1—C2—H2B	111.0	C24—C23—H23	120.7
C3—C2—H2B	111.0	C22—C23—H23	120.7
H2A—C2—H2B	109.0	C25—C24—C23	121.0 (3)
C4—C3—C2	107.4 (3)	C25—C24—H24	119.5
C4—C3—H3A	110.2	C23—C24—H24	119.5
C2—C3—H3A	110.2	C24—C25—C26	120.2 (4)
C4—C3—H3B	110.2	C24—C25—H25	119.9
C2—C3—H3B	110.2	C26—C25—H25	119.9
H3A—C3—H3B	108.5	C21—C26—C25	121.0 (3)
C3—C4—C5	110.3 (3)	C21—C26—H26	119.5
C3—C4—H4A	109.6	C25—C26—H26	119.5
C5—C4—H4A	109.6	C36—C31—C32	117.9 (2)
C3—C4—H4B	109.6	C36—C31—P1	124.15 (18)
C5—C4—H4B	109.6	C32—C31—P1	117.8 (2)
H4A—C4—H4B	108.1	C33—C32—C31	120.5 (3)
N1—C5—C4	104.0 (3)	C33—C32—H32	119.8
N1—C5—H5A	110.9	C31—C32—H32	119.8
C4—C5—H5A	110.9	C34—C33—C32	119.5 (3)
N1—C5—H5B	110.9	C34—C33—H33	120.2
C4—C5—H5B	110.9	C32—C33—H33	120.2
H5A—C5—H5B	109.0	C35—C34—C33	121.4 (3)
C31—P1—C11	104.79 (13)	C35—C34—H34	119.3
C31—P1—C21	101.92 (13)	C33—C34—H34	119.3
C11—P1—C21	105.22 (13)	C34—C35—C36	118.9 (3)
C31—P1—Ni	115.11 (9)	C34—C35—H35	120.6
C11—P1—Ni	108.83 (10)	C36—C35—H35	120.6
C21—P1—Ni	119.61 (10)	C31—C36—C35	121.8 (2)
C16—C11—C12	118.6 (3)	C31—C36—H36	119.1
C16—C11—P1	124.0 (2)	C35—C36—H36	119.1
C12—C11—P1	117.4 (2)	Cl2—C37—Cl3	110.5 (2)
C13—C12—C11	119.7 (3)	Cl2—C37—Cl1	108.6 (2)
C13—C12—H12	120.2	Cl3—C37—Cl1	108.5 (2)
C11—C12—H12	120.2	Cl2—C37—H37	109.7
C14—C13—C12	120.7 (3)	Cl3—C37—H37	109.7
C14—C13—H13	119.6	Cl1—C37—H37	109.8

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C37—H37···S1	0.96	2.40	3.280 (1)	152