A triclinic polymorph of tri­cyclo­hexyl­phosphane sulfide: crystal structure and Hirshfeld surface analysis

Tan, Y.J.; Yeo, C.I.; Halcovitch, N.R.; Jotani, M.M.; Tiekink, E.R.T.

doi:10.1107/S205698901700353X

A triclinic polymorph of tricyclohexylphosphane sulfide: crystal structure and Hirshfeld surface analysis

Y. J. Tan, C. I. Yeo, N. R. Halcovitch, M. M. Jotani and E. R. T. Tiekink

The conformation found for (C₆H₁₁)₃P=S in the triclinic polymorph lacks the mirror symmetry found in the orthorhombic form. Nevertheless, the conformations are in essential agreement. In the crystal, linear supramolecular chains are sustained by methine-C—H

S(thione) interactions.

Keywords: crystal structure; triorganophosphane sulfide; polymorph; Hirshfeld surface analysis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S205698901700353X/hb7665sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S205698901700353X/hb7665Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901700353X/hb7665Isup3.cml Supplementary material

CCDC reference: 1536014

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.037
wR factor = 0.097
Data-to-parameter ratio = 23.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    S1     --  P1      ..        8.3 s.u.

Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.035 Check

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.007 Degree
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        727 Note
PLAT951_ALERT_5_G Calculated (ThMax) and CIF-Reported Kmax Differ           2 Units
PLAT957_ALERT_1_G Calculated (ThMax) and Actual (FCF) Kmax Differ           2 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         14 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

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

Computing details top

Data collection: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); cell refinement: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); data reduction: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Tricyclohexyl-λ⁵-phosphanethione top

Crystal data top

C₁₈H₃₃PS	Z = 2
M_r = 312.47	F(000) = 344
Triclinic, P1	D_x = 1.170 Mg m⁻³
a = 6.6400 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.8089 (9) Å	Cell parameters from 4800 reflections
c = 12.8818 (10) Å	θ = 3.7–29.5°
α = 103.430 (7)°	µ = 0.26 mm⁻¹
β = 98.467 (7)°	T = 100 K
γ = 91.912 (7)°	Prism, colourless
V = 887.26 (12) Å³	0.40 × 0.20 × 0.17 mm

Data collection top

Agilent SuperNova, Dual, Mo at zero, AtlasS2 diffractometer	4208 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	3739 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.022
ω scans	θ_max = 29.7°, θ_min = 2.8°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku Oxford Diffraction, 2015)	h = −8→9
T_min = 0.926, T_max = 1.000	k = −13→12
8658 measured reflections	l = −16→17

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.0433P)² + 0.4808P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
4208 reflections	Δρ_max = 0.47 e Å⁻³
181 parameters	Δρ_min = −0.35 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.28983 (5)	0.28303 (4)	0.60522 (3)	0.02266 (11)
P1	0.58024 (5)	0.29616 (3)	0.66467 (3)	0.01328 (10)
C1	0.6361 (2)	0.17062 (13)	0.73806 (11)	0.0155 (3)
H1	0.5711	0.0898	0.6877	0.019*
C2	0.8619 (2)	0.14502 (14)	0.76697 (12)	0.0176 (3)
H2A	0.9269	0.1300	0.7012	0.021*
H2B	0.9347	0.2205	0.8197	0.021*
C3	0.8780 (2)	0.02835 (15)	0.81546 (12)	0.0215 (3)
H3A	0.8173	−0.0484	0.7599	0.026*
H3B	1.0238	0.0157	0.8371	0.026*
C4	0.7689 (2)	0.04367 (15)	0.91382 (12)	0.0215 (3)
H4A	0.8396	0.1143	0.9727	0.026*
H4B	0.7751	−0.0355	0.9400	0.026*
C5	0.5457 (2)	0.07171 (15)	0.88609 (12)	0.0210 (3)
H5A	0.4708	−0.0033	0.8337	0.025*
H5B	0.4820	0.0873	0.9524	0.025*
C6	0.5286 (2)	0.18808 (14)	0.83768 (12)	0.0183 (3)
H6A	0.5910	0.2649	0.8927	0.022*
H6B	0.3828	0.2012	0.8168	0.022*
C7	0.7413 (2)	0.27103 (13)	0.55847 (11)	0.0151 (3)
H7	0.8872	0.2799	0.5940	0.018*
C8	0.7119 (2)	0.37069 (14)	0.49033 (12)	0.0209 (3)
H8A	0.5663	0.3672	0.4581	0.025*
H8B	0.7496	0.4570	0.5376	0.025*
C9	0.8424 (3)	0.34686 (15)	0.40031 (12)	0.0252 (3)
H9A	0.8170	0.4105	0.3565	0.030*
H9B	0.9886	0.3571	0.4325	0.030*
C10	0.7926 (3)	0.21275 (15)	0.32763 (12)	0.0254 (3)
H10A	0.8810	0.1984	0.2710	0.030*
H10B	0.6488	0.2042	0.2915	0.030*
C11	0.8260 (2)	0.11291 (14)	0.39418 (12)	0.0203 (3)
H11A	0.7889	0.0267	0.3465	0.024*
H11B	0.9721	0.1172	0.4257	0.024*
C12	0.6967 (2)	0.13517 (14)	0.48499 (11)	0.0178 (3)
H12A	0.7261	0.0720	0.5290	0.021*
H12B	0.5503	0.1224	0.4532	0.021*
C13	0.6633 (2)	0.45629 (13)	0.75178 (11)	0.0155 (3)
H13	0.6674	0.5136	0.7012	0.019*
C14	0.5091 (2)	0.51104 (15)	0.82558 (12)	0.0202 (3)
H14A	0.3716	0.5046	0.7820	0.024*
H14B	0.5027	0.4609	0.8804	0.024*
C15	0.5722 (2)	0.65042 (15)	0.88193 (12)	0.0219 (3)
H15A	0.5689	0.7014	0.8271	0.026*
H15B	0.4736	0.6838	0.9304	0.026*
C16	0.7857 (2)	0.66490 (14)	0.94750 (12)	0.0205 (3)
H16A	0.7863	0.6202	1.0064	0.025*
H16B	0.8246	0.7563	0.9807	0.025*
C17	0.9411 (2)	0.60985 (15)	0.87601 (13)	0.0242 (3)
H17A	1.0768	0.6154	0.9212	0.029*
H17B	0.9516	0.6609	0.8222	0.029*
C18	0.8796 (2)	0.47037 (14)	0.81713 (12)	0.0200 (3)
H18A	0.8846	0.4175	0.8706	0.024*
H18B	0.9779	0.4392	0.7678	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01585 (19)	0.0258 (2)	0.0254 (2)	0.00077 (14)	0.00114 (14)	0.00571 (15)
P1	0.01333 (18)	0.01384 (18)	0.01275 (17)	0.00045 (12)	0.00201 (12)	0.00351 (13)
C1	0.0171 (7)	0.0152 (7)	0.0156 (6)	0.0008 (5)	0.0049 (5)	0.0050 (5)
C2	0.0175 (7)	0.0190 (7)	0.0197 (7)	0.0038 (5)	0.0062 (5)	0.0090 (6)
C3	0.0237 (8)	0.0200 (8)	0.0248 (8)	0.0066 (6)	0.0081 (6)	0.0101 (6)
C4	0.0263 (8)	0.0204 (8)	0.0222 (7)	0.0040 (6)	0.0074 (6)	0.0116 (6)
C5	0.0240 (8)	0.0209 (8)	0.0217 (7)	0.0008 (6)	0.0083 (6)	0.0095 (6)
C6	0.0197 (7)	0.0197 (7)	0.0189 (7)	0.0034 (5)	0.0074 (5)	0.0084 (6)
C7	0.0200 (7)	0.0129 (7)	0.0130 (6)	0.0013 (5)	0.0047 (5)	0.0026 (5)
C8	0.0334 (8)	0.0140 (7)	0.0174 (7)	0.0034 (6)	0.0080 (6)	0.0054 (5)
C9	0.0427 (10)	0.0172 (8)	0.0207 (7)	0.0040 (6)	0.0140 (7)	0.0089 (6)
C10	0.0429 (10)	0.0208 (8)	0.0152 (7)	0.0069 (7)	0.0094 (6)	0.0061 (6)
C11	0.0293 (8)	0.0151 (7)	0.0169 (7)	0.0029 (6)	0.0066 (6)	0.0026 (5)
C12	0.0249 (7)	0.0129 (7)	0.0165 (7)	0.0009 (5)	0.0058 (5)	0.0039 (5)
C13	0.0162 (7)	0.0158 (7)	0.0146 (6)	0.0008 (5)	0.0029 (5)	0.0034 (5)
C14	0.0166 (7)	0.0219 (8)	0.0194 (7)	0.0024 (5)	0.0032 (5)	−0.0006 (6)
C15	0.0252 (8)	0.0205 (8)	0.0185 (7)	0.0075 (6)	0.0025 (6)	0.0012 (6)
C16	0.0250 (8)	0.0150 (7)	0.0194 (7)	−0.0003 (5)	0.0024 (6)	0.0004 (5)
C17	0.0205 (8)	0.0203 (8)	0.0282 (8)	−0.0052 (6)	0.0047 (6)	−0.0011 (6)
C18	0.0164 (7)	0.0177 (7)	0.0233 (7)	−0.0001 (5)	0.0028 (6)	0.0003 (6)

Geometric parameters (Å, º) top

S1—P1	1.9548 (5)	C9—H9A	0.9900
P1—C1	1.8435 (14)	C9—H9B	0.9900
P1—C7	1.8350 (14)	C10—C11	1.529 (2)
P1—C13	1.8468 (15)	C10—H10A	0.9900
C1—C6	1.5356 (18)	C10—H10B	0.9900
C1—C2	1.5408 (19)	C11—C12	1.5302 (19)
C1—H1	1.0000	C11—H11A	0.9900
C2—C3	1.532 (2)	C11—H11B	0.9900
C2—H2A	0.9900	C12—H12A	0.9900
C2—H2B	0.9900	C12—H12B	0.9900
C3—C4	1.530 (2)	C13—C18	1.5376 (19)
C3—H3A	0.9900	C13—C14	1.5391 (19)
C3—H3B	0.9900	C13—H13	1.0000
C4—C5	1.530 (2)	C14—C15	1.527 (2)
C4—H4A	0.9900	C14—H14A	0.9900
C4—H4B	0.9900	C14—H14B	0.9900
C5—C6	1.529 (2)	C15—C16	1.523 (2)
C5—H5A	0.9900	C15—H15A	0.9900
C5—H5B	0.9900	C15—H15B	0.9900
C6—H6A	0.9900	C16—C17	1.527 (2)
C6—H6B	0.9900	C16—H16A	0.9900
C7—C8	1.540 (2)	C16—H16B	0.9900
C7—C12	1.5437 (19)	C17—C18	1.533 (2)
C7—H7	1.0000	C17—H17A	0.9900
C8—C9	1.528 (2)	C17—H17B	0.9900
C8—H8A	0.9900	C18—H18A	0.9900
C8—H8B	0.9900	C18—H18B	0.9900
C9—C10	1.528 (2)

C7—P1—C1	105.82 (6)	C10—C9—H9B	109.5
C7—P1—C13	105.70 (6)	C8—C9—H9B	109.5
C1—P1—C13	111.43 (6)	H9A—C9—H9B	108.1
C7—P1—S1	112.11 (5)	C9—C10—C11	110.38 (12)
C1—P1—S1	109.99 (5)	C9—C10—H10A	109.6
C13—P1—S1	111.60 (5)	C11—C10—H10A	109.6
C6—C1—C2	110.75 (11)	C9—C10—H10B	109.6
C6—C1—P1	111.78 (10)	C11—C10—H10B	109.6
C2—C1—P1	117.32 (10)	H10A—C10—H10B	108.1
C6—C1—H1	105.3	C12—C11—C10	110.93 (12)
C2—C1—H1	105.3	C12—C11—H11A	109.5
P1—C1—H1	105.3	C10—C11—H11A	109.5
C3—C2—C1	110.13 (12)	C12—C11—H11B	109.5
C3—C2—H2A	109.6	C10—C11—H11B	109.5
C1—C2—H2A	109.6	H11A—C11—H11B	108.0
C3—C2—H2B	109.6	C11—C12—C7	111.43 (12)
C1—C2—H2B	109.6	C11—C12—H12A	109.3
H2A—C2—H2B	108.1	C7—C12—H12A	109.3
C4—C3—C2	111.72 (12)	C11—C12—H12B	109.3
C4—C3—H3A	109.3	C7—C12—H12B	109.3
C2—C3—H3A	109.3	H12A—C12—H12B	108.0
C4—C3—H3B	109.3	C18—C13—C14	110.45 (11)
C2—C3—H3B	109.3	C18—C13—P1	115.68 (10)
H3A—C3—H3B	107.9	C14—C13—P1	113.42 (10)
C3—C4—C5	111.30 (12)	C18—C13—H13	105.4
C3—C4—H4A	109.4	C14—C13—H13	105.4
C5—C4—H4A	109.4	P1—C13—H13	105.4
C3—C4—H4B	109.4	C15—C14—C13	110.25 (12)
C5—C4—H4B	109.4	C15—C14—H14A	109.6
H4A—C4—H4B	108.0	C13—C14—H14A	109.6
C6—C5—C4	111.10 (12)	C15—C14—H14B	109.6
C6—C5—H5A	109.4	C13—C14—H14B	109.6
C4—C5—H5A	109.4	H14A—C14—H14B	108.1
C6—C5—H5B	109.4	C16—C15—C14	111.29 (12)
C4—C5—H5B	109.4	C16—C15—H15A	109.4
H5A—C5—H5B	108.0	C14—C15—H15A	109.4
C5—C6—C1	111.04 (12)	C16—C15—H15B	109.4
C5—C6—H6A	109.4	C14—C15—H15B	109.4
C1—C6—H6A	109.4	H15A—C15—H15B	108.0
C5—C6—H6B	109.4	C15—C16—C17	110.86 (12)
C1—C6—H6B	109.4	C15—C16—H16A	109.5
H6A—C6—H6B	108.0	C17—C16—H16A	109.5
C8—C7—C12	110.18 (11)	C15—C16—H16B	109.5
C8—C7—P1	111.69 (10)	C17—C16—H16B	109.5
C12—C7—P1	110.46 (10)	H16A—C16—H16B	108.1
C8—C7—H7	108.1	C16—C17—C18	111.30 (12)
C12—C7—H7	108.1	C16—C17—H17A	109.4
P1—C7—H7	108.1	C18—C17—H17A	109.4
C9—C8—C7	111.28 (12)	C16—C17—H17B	109.4
C9—C8—H8A	109.4	C18—C17—H17B	109.4
C7—C8—H8A	109.4	H17A—C17—H17B	108.0
C9—C8—H8B	109.4	C17—C18—C13	111.07 (12)
C7—C8—H8B	109.4	C17—C18—H18A	109.4
H8A—C8—H8B	108.0	C13—C18—H18A	109.4
C10—C9—C8	110.78 (13)	C17—C18—H18B	109.4
C10—C9—H9A	109.5	C13—C18—H18B	109.4
C8—C9—H9A	109.5	H18A—C18—H18B	108.0

C7—P1—C1—C6	173.93 (10)	P1—C7—C8—C9	−178.51 (10)
C13—P1—C1—C6	59.51 (11)	C7—C8—C9—C10	57.32 (17)
S1—P1—C1—C6	−64.79 (10)	C8—C9—C10—C11	−57.82 (18)
C7—P1—C1—C2	44.45 (12)	C9—C10—C11—C12	57.32 (17)
C13—P1—C1—C2	−69.97 (12)	C10—C11—C12—C7	−56.28 (16)
S1—P1—C1—C2	165.73 (9)	C8—C7—C12—C11	54.86 (16)
C6—C1—C2—C3	56.61 (16)	P1—C7—C12—C11	178.74 (10)
P1—C1—C2—C3	−173.43 (10)	C7—P1—C13—C18	−67.43 (12)
C1—C2—C3—C4	−56.03 (16)	C1—P1—C13—C18	47.06 (12)
C2—C3—C4—C5	55.46 (17)	S1—P1—C13—C18	170.45 (9)
C3—C4—C5—C6	−54.99 (17)	C7—P1—C13—C14	163.46 (10)
C4—C5—C6—C1	55.98 (16)	C1—P1—C13—C14	−82.05 (11)
C2—C1—C6—C5	−57.02 (16)	S1—P1—C13—C14	41.34 (11)
P1—C1—C6—C5	170.15 (10)	C18—C13—C14—C15	56.93 (16)
C1—P1—C7—C8	−179.57 (10)	P1—C13—C14—C15	−171.34 (10)
C13—P1—C7—C8	−61.26 (11)	C13—C14—C15—C16	−57.70 (16)
S1—P1—C7—C8	60.53 (11)	C14—C15—C16—C17	56.93 (17)
C1—P1—C7—C12	57.43 (11)	C15—C16—C17—C18	−55.49 (18)
C13—P1—C7—C12	175.73 (9)	C16—C17—C18—C13	55.34 (17)
S1—P1—C7—C12	−62.47 (10)	C14—C13—C18—C17	−55.97 (16)
C12—C7—C8—C9	−55.35 (16)	P1—C13—C18—C17	173.48 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···S1ⁱ	1.00	2.65	3.5961 (14)	157

Symmetry code: (i) x+1, y, z.

Geometric parameters (Å, °) for the triclinic (I) and orthorhombic (II) polymorphs of Cy₃P═S top

Parameter	triclinic polymorph	orthorhombic polymorph^a
P1═S1	1.9548 (5)	1.9612 (11)
P1—C1	1.8435 (14)	1.842 (3)
P1—C7	1.8350 (14)	1.836 (2)
P1—C13	1.8468 (15)	1.836 (2)
S1—P1—C1	109.99 (5)	112.16 (11)
S1—P1—C7	112.11 (5)	110.15 (7)
S1—P1—C13	111.60 (5)	110.15 (7)
C1—P1—C7	105.82 (6)	105.22 (9)
C1—P1—C13	105.70 (6)	105.22 (9)
C7—P1—C13	111.43 (6)	113.80 (10)

Notes: (a) the molecule has crystallographic mirror symmetry with the S1, P1 and C1 atoms lying on the plane.

Percentage contributions of the different intermolecular contacts to the Hirshfeld surface in (I) and (II) top

Contact	% contribution in (I)	% contribution in (II)
H···H	89.8	88.8
S···H/H···S	10.2	11.2

Short interatomic contacts in (I). top

Contact	distance	symmetry operation
H6A···H15B	2.32	1 - x, 1 - y, 2 - z
H10B···H15A	2.37	1 - x, 1 - y, 1 - z

Physiochemical properties for polymorphs (I) and (II) top

Property	(I)	(II)
Volume, V (Å³)	436.83	430.96
Surface area, A (Å²)	351.03	345.83
A:V (Å^-1)	0.804	0.802
Globularity, G	0.793	0.798
Asphericity, Ω	0.051	0.046
Density (g cm^-3)	1.170	1.186
Packing index (%)	68.6	68.4

Geometric parameters (Å, °) for selected R₃P═S molecules top

R	P═S	S—P—C	C—P—C	Reference
Me^a	1.9664 (7)	112.88 (6)–113.22 (8)	105.33 (8)–106.53 (8)	Tasker et al., 2005
iPr^a	1.926 (3)	110.08 (19)–112.3 (2)	103.88 (19)–116.3 (4)	Staples et al., 2001
tBu^b	1.9627 (15)	109.29 (14)	109.65 (19)	Steinberger et al., 2001
Ph^c^,^d	1.9554 (7)	112.16 (6)–113.47 (6)	103.70 (8)–107.76 (8)	Foces-Foces & Llamas-Saiz, 1998
	1.9547 (7)	112.28 (7)–113.67 (6)	103.12 (8)–107.53 (9)
Ph^d^,^e	1.9544 (9)	112.47 (7)–113.99 (7)	103.43 (8)–106.83 (8)	Ziemer et al., 2000
	1.9529 (8)	111.97 (7)–113.19 (7)	103.61 (8)–107.38 (8)
2-tolyl^d	1.953 (6)	110.7 (3)–114.2 (3)	101.4 (3)–110.6 (4)	Cameron & Dahlèn, 1975
	1.942 (5)	111.6 (2)–114.3 (2)	104.9 (3)–107.9 (3)
3-tolyl	1.937 (4)	112.1 (8)–112.6 (4)	105.5 (7)–108.2 (10)	Cameron et al., 1978
4-FPh	1.9540 (9)	113.27 (8)–113.59 (8)	104.97 (10)–105.92 (10)	Barnes et al., 2007
2,4,6-Me₃Ph	1.9748 (13)	107.32 (11)–109.49 (12)	108.90 (16)–112.45 (15)	Garland et al., 2013
2,4,6-(OMe)₃Ph	1.9619 (12)	109.22 (11)–116.15 (11)	100.77 (14)–110.58 (14)	Finnen et al., 1994
2-(Me₂NCH₂)₃Ph	1.9622 (17)	110.66 (8)–116.15 (10)	103.51 (13)–106.33 (11)	Rotar et al., 2010
Cy^a^,^f	1.9612 (11)	110.15 (7)–112.16 (11)	105.22 (9)–113.80 (10)	Reibenspies et al., 1996
Cy^e	1.9548 (5)	109.99 (5)–112.11 (5)	105.70 (6)–111.43 (6)	this work

Notes: (a) The molecule has crystallographic mirror symmetry with the S1, P1 and C1 atoms lying on the plane; (b) the molecule has crystallographic threefold symmetry with the S1 and P1 atoms lying on the axis; (c) monoclinic polymorph; (d) two independent molecules in the asymmetric unit; (e) triclinic polymorph; (f) orthorhombic polymorph.

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A triclinic polymorph of tri­cyclo­hexyl­phosphane sulfide: crystal structure and Hirshfeld surface analysis

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A triclinic polymorph of tricyclohexylphosphane sulfide: crystal structure and Hirshfeld surface analysis