3-Cyclo­hexyl-4-(3-methyl-3-phenyl­cyclo­butyl)-1,3-thia­zole-2(3H)-thione

The cyclo­hexyl ring of the title compound, C₂₀H₂₅NS₂, has a chair conformation. The dihedral angle between the thia­zole and phenyl rings is 89.70 (2)°. The crystal structure involves two weak intramolecular C—H...S hydrogen-bond contacts.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.031
• wR factor = 0.070
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S2     -   C14     ..       6.29 su

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.86
           From the CIF: _reflns_number_total               4306
           Count of symmetry unique reflns         2450
           Completeness (_total/calc)            175.76%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1856
           Fraction of Friedel pairs measured     0.758
           Are heavy atom types Z>Si present          yes

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

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

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Computing details

Data collection: COLLECT (Bruker–Nonius, 2002); cell refinement: EVALCCD (Bruker–Nonius, 2002); data reduction: EVALCCD; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL.

3-Cyclohexyl-4-(3-methyl-3-phenylcyclobutyl)-1,3-thiazole-2(3H)-thione

Crystal data

C20H25NS2	F(000) = 736
Mr = 343.53	Dx = 1.262 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 264 reflections
a = 9.9686 (8) Å	θ = 6.0–20.0°
b = 12.2843 (8) Å	µ = 0.29 mm^−1
c = 14.7707 (3) Å	T = 100 K
V = 1808.8 (2) Å^3	Block, colourless
Z = 4	0.30 × 0.28 × 0.23 mm

Data collection

Nonius KappaCCD diffractometer	4306 independent reflections
Radiation source: fine-focus sealed tube	3828 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
Detector resolution: 9 pixels mm^-1	θmax = 27.9°, θmin = 3.2°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	k = −16→16
Tmin = 0.916, Tmax = 0.935	l = −19→19
27385 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Only H-atom coordinates refined
wR(F^2) = 0.070	w = 1/[σ^2(Fo^2) + (0.039P)^2 + 0.201P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
4306 reflections	Δρmax = 0.23 e Å^−3
283 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Absolute structure: Flack (1983), 1856 Freidel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (5)

Special details

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
S1	0.15976 (4)	0.68713 (3)	0.01800 (3)	0.01436 (10)
S2	−0.11815 (4)	0.65353 (3)	0.08574 (3)	0.01770 (11)
N1	0.11752 (14)	0.58259 (10)	0.16288 (9)	0.0101 (3)
C1	0.44514 (18)	0.19189 (14)	0.11652 (11)	0.0166 (4)
C2	0.4973 (2)	0.11228 (15)	0.05902 (12)	0.0192 (4)
C3	0.62952 (19)	0.11879 (14)	0.03051 (12)	0.0188 (4)
C4	0.70939 (18)	0.20476 (15)	0.05863 (11)	0.0176 (4)
C5	0.65786 (18)	0.28444 (14)	0.11541 (11)	0.0152 (4)
C6	0.52396 (17)	0.27913 (13)	0.14524 (11)	0.0117 (3)
C7	0.47087 (16)	0.36513 (13)	0.20865 (11)	0.0121 (3)
C8	0.52228 (19)	0.34469 (17)	0.30462 (12)	0.0179 (4)
C9	0.48996 (17)	0.48595 (14)	0.17840 (12)	0.0132 (3)
C10	0.31703 (17)	0.38502 (14)	0.20951 (12)	0.0133 (3)
C11	0.34450 (17)	0.51059 (13)	0.20972 (11)	0.0112 (3)
C12	0.25767 (16)	0.57763 (13)	0.14866 (11)	0.0103 (3)
C13	0.29573 (17)	0.63181 (13)	0.07376 (11)	0.0128 (3)
C14	0.04775 (17)	0.63528 (13)	0.09680 (11)	0.0133 (3)
C15	0.05573 (17)	0.53817 (13)	0.24697 (11)	0.0114 (3)
C16	−0.00798 (19)	0.62749 (14)	0.30485 (12)	0.0156 (4)
C17	−0.0537 (2)	0.57754 (16)	0.39491 (13)	0.0207 (4)
C18	−0.1497 (2)	0.48230 (15)	0.37902 (14)	0.0235 (4)
C19	−0.08497 (18)	0.39573 (15)	0.31933 (13)	0.0191 (4)
C20	−0.03935 (19)	0.44332 (14)	0.22870 (12)	0.0161 (4)
H1	0.348 (2)	0.1830 (19)	0.1421 (15)	0.040*
H2	0.443 (2)	0.052 (2)	0.0419 (16)	0.040*
H3	0.664 (2)	0.0652 (19)	−0.0092 (17)	0.040*
H4	0.795 (3)	0.214 (2)	0.0379 (16)	0.040*
H5	0.712 (2)	0.346 (2)	0.1360 (16)	0.040*
H8A	0.481 (2)	0.399 (2)	0.3464 (17)	0.040*
H8B	0.619 (3)	0.3418 (19)	0.3058 (15)	0.040*
H8C	0.492 (2)	0.273 (2)	0.3297 (16)	0.040*
H9A	0.498 (2)	0.4902 (19)	0.1122 (17)	0.040*
H9B	0.563 (2)	0.527 (2)	0.2108 (15)	0.040*
H10A	0.268 (2)	0.357 (2)	0.2625 (17)	0.040*
H10B	0.270 (2)	0.363 (2)	0.1546 (17)	0.040*
H11	0.345 (2)	0.5446 (18)	0.2735 (16)	0.040*
H13	0.383 (3)	0.6400 (19)	0.0477 (15)	0.040*
H15	0.133 (3)	0.505 (2)	0.2786 (16)	0.040*
H16A	0.063 (2)	0.685 (2)	0.3177 (15)	0.040*
H16B	−0.086 (2)	0.657 (2)	0.2728 (16)	0.040*
H17A	−0.092 (2)	0.636 (2)	0.4335 (16)	0.040*
H17B	0.022 (3)	0.554 (2)	0.4261 (17)	0.040*
H18A	−0.175 (3)	0.4497 (19)	0.4348 (17)	0.040*
H18B	−0.233 (2)	0.511 (2)	0.3472 (17)	0.040*
H19A	−0.006 (3)	0.363 (2)	0.3497 (16)	0.040*
H19B	−0.149 (2)	0.3312 (19)	0.3059 (15)	0.040*
H20A	−0.117 (3)	0.471 (2)	0.1941 (15)	0.040*
H20B	0.002 (3)	0.385 (2)	0.1922 (16)	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0176 (2)	0.01383 (19)	0.01165 (18)	−0.00148 (16)	−0.00226 (16)	0.00350 (16)
S2	0.0130 (2)	0.0172 (2)	0.0230 (2)	0.00020 (16)	−0.00675 (17)	0.00499 (19)
N1	0.0113 (6)	0.0088 (6)	0.0102 (6)	−0.0007 (5)	−0.0007 (5)	0.0013 (5)
C1	0.0190 (9)	0.0129 (8)	0.0178 (8)	0.0019 (7)	0.0013 (7)	0.0022 (7)
C2	0.0262 (10)	0.0119 (8)	0.0197 (9)	−0.0001 (8)	−0.0019 (8)	−0.0011 (7)
C3	0.0296 (10)	0.0146 (8)	0.0123 (8)	0.0073 (7)	0.0020 (7)	0.0002 (7)
C4	0.0169 (9)	0.0230 (9)	0.0129 (8)	0.0039 (8)	0.0039 (7)	0.0035 (8)
C5	0.0140 (8)	0.0166 (8)	0.0148 (8)	0.0008 (7)	−0.0013 (7)	−0.0004 (7)
C6	0.0131 (8)	0.0125 (8)	0.0097 (7)	0.0028 (6)	−0.0011 (6)	0.0017 (6)
C7	0.0113 (8)	0.0113 (8)	0.0138 (8)	0.0017 (6)	−0.0006 (6)	0.0008 (6)
C8	0.0177 (9)	0.0228 (9)	0.0132 (8)	0.0063 (8)	−0.0011 (7)	−0.0006 (8)
C9	0.0105 (8)	0.0118 (8)	0.0174 (8)	0.0012 (7)	−0.0002 (7)	0.0001 (7)
C10	0.0120 (8)	0.0118 (8)	0.0160 (8)	0.0015 (7)	0.0014 (7)	0.0018 (7)
C11	0.0092 (8)	0.0123 (8)	0.0122 (7)	−0.0003 (6)	−0.0009 (6)	−0.0001 (6)
C12	0.0097 (8)	0.0093 (8)	0.0120 (8)	−0.0018 (6)	−0.0008 (6)	−0.0018 (6)
C13	0.0129 (8)	0.0125 (8)	0.0131 (8)	−0.0007 (6)	−0.0007 (6)	0.0000 (7)
C14	0.0167 (8)	0.0090 (7)	0.0142 (8)	−0.0021 (6)	−0.0021 (7)	−0.0013 (7)
C15	0.0102 (8)	0.0123 (8)	0.0117 (8)	−0.0015 (6)	0.0012 (6)	0.0037 (7)
C16	0.0184 (9)	0.0127 (9)	0.0157 (8)	0.0020 (7)	0.0019 (7)	0.0003 (7)
C17	0.0228 (10)	0.0206 (9)	0.0188 (9)	0.0037 (8)	0.0075 (8)	0.0000 (8)
C18	0.0218 (10)	0.0218 (9)	0.0270 (10)	0.0015 (8)	0.0110 (8)	0.0057 (8)
C19	0.0167 (9)	0.0138 (8)	0.0270 (10)	0.0004 (7)	0.0061 (8)	0.0048 (8)
C20	0.0171 (10)	0.0098 (8)	0.0213 (9)	0.0006 (7)	0.0015 (7)	0.0028 (7)

Geometric parameters (Å, º)

S1—C13	1.725 (2)	C9—H9B	1.01 (3)
S1—C14	1.734 (2)	C10—C11	1.567 (2)
S2—C14	1.677 (2)	C10—H10A	0.98 (2)
N1—C14	1.362 (2)	C10—H10B	0.97 (3)
N1—C12	1.414 (2)	C11—C12	1.497 (2)
N1—C15	1.490 (2)	C11—H11	1.03 (2)
C1—C6	1.395 (2)	C12—C13	1.346 (2)
C1—C2	1.396 (3)	C13—H13	0.96 (3)
C1—H1	1.05 (2)	C15—C20	1.526 (2)
C2—C3	1.386 (3)	C15—C16	1.529 (2)
C2—H2	0.95 (3)	C15—H15	0.98 (3)
C3—C4	1.386 (3)	C16—C17	1.534 (2)
C3—H3	0.95 (3)	C16—H16A	1.02 (3)
C4—C5	1.388 (2)	C16—H16B	0.98 (2)
C4—H4	0.91 (2)	C17—C18	1.530 (3)
C5—C6	1.407 (2)	C17—H17A	1.00 (3)
C5—H5	0.98 (2)	C17—H17B	0.93 (3)
C6—C7	1.508 (2)	C18—C19	1.525 (3)
C7—C8	1.528 (2)	C18—H18A	0.95 (2)
C7—C10	1.553 (2)	C18—H18B	1.01 (3)
C7—C9	1.562 (2)	C19—C20	1.530 (3)
C8—H8A	0.99 (3)	C19—H19A	1.00 (3)
C8—H8B	0.96 (2)	C19—H19B	1.04 (2)
C8—H8C	1.00 (3)	C20—H20A	0.99 (3)
C9—C11	1.552 (2)	C20—H20B	0.98 (3)
C9—H9A	0.98 (2)
C13—S1—C14	92.34 (8)	C12—C11—H11	109.2 (13)
C14—N1—C12	114.74 (14)	C9—C11—H11	110.5 (14)
C14—N1—C15	124.08 (14)	C10—C11—H11	113.6 (13)
C12—N1—C15	121.09 (13)	C13—C12—N1	112.29 (15)
C6—C1—C2	120.89 (17)	C13—C12—C11	127.19 (15)
C6—C1—H1	119.5 (13)	N1—C12—C11	120.36 (14)
C2—C1—H1	119.5 (13)	C12—C13—S1	111.5 (1)
C3—C2—C1	119.92 (17)	C12—C13—H13	129.7 (14)
C3—C2—H2	120.4 (15)	S1—C13—H13	118.7 (14)
C1—C2—H2	119.6 (15)	N1—C14—S2	129.6 (1)
C2—C3—C4	119.94 (17)	N1—C14—S1	109.1 (1)
C2—C3—H3	119.8 (15)	S2—C14—S1	121.4 (1)
C4—C3—H3	120.3 (15)	N1—C15—C20	112.90 (14)
C3—C4—C5	120.39 (17)	N1—C15—C16	112.02 (13)
C3—C4—H4	122.2 (16)	C20—C15—C16	112.87 (14)
C5—C4—H4	117.3 (16)	N1—C15—H15	102.9 (14)
C4—C5—C6	120.51 (16)	C20—C15—H15	104.9 (14)
C4—C5—H5	122.2 (14)	C16—C15—H15	110.5 (14)
C6—C5—H5	117.3 (14)	C15—C16—C17	108.74 (14)
C1—C6—C5	118.34 (16)	C15—C16—H16A	108.3 (13)
C1—C6—C7	121.97 (15)	C17—C16—H16A	108.9 (13)
C5—C6—C7	119.66 (15)	C15—C16—H16B	109.1 (14)
C6—C7—C8	110.09 (13)	C17—C16—H16B	109.6 (14)
C6—C7—C10	117.51 (14)	H16A—C16—H16B	112.2 (19)
C8—C7—C10	110.45 (14)	C18—C17—C16	111.02 (16)
C6—C7—C9	116.45 (14)	C18—C17—H17A	113.7 (13)
C8—C7—C9	112.38 (14)	C16—C17—H17A	108.7 (13)
C10—C7—C9	88.47 (12)	C18—C17—H17B	110.3 (15)
C7—C8—H8A	109.2 (14)	C16—C17—H17B	108.2 (15)
C7—C8—H8B	111.0 (13)	H17A—C17—H17B	105 (2)
H8A—C8—H8B	115 (2)	C19—C18—C17	110.94 (15)
C7—C8—H8C	112.8 (14)	C19—C18—H18A	108.6 (15)
H8A—C8—H8C	103.3 (19)	C17—C18—H18A	110.7 (14)
H8B—C8—H8C	105 (2)	C19—C18—H18B	108.5 (14)
C11—C9—C7	89.21 (12)	C17—C18—H18B	108.7 (14)
C11—C9—H9A	111.5 (14)	H18A—C18—H18B	109 (2)
C7—C9—H9A	110.2 (14)	C18—C19—C20	111.42 (15)
C11—C9—H9B	115.7 (13)	C18—C19—H19A	111.0 (14)
C7—C9—H9B	115.6 (14)	C20—C19—H19A	108.2 (14)
H9A—C9—H9B	112.6 (19)	C18—C19—H19B	112.7 (13)
C7—C10—C11	88.99 (12)	C20—C19—H19B	107.9 (13)
C7—C10—H10A	116.3 (14)	H19A—C19—H19B	105.4 (18)
C11—C10—H10A	115.4 (15)	C15—C20—C19	108.77 (15)
C7—C10—H10B	115.0 (14)	C15—C20—H20A	108.5 (15)
C11—C10—H10B	111.0 (15)	C19—C20—H20A	110.5 (14)
H10A—C10—H10B	109.1 (19)	C15—C20—H20B	113.1 (15)
C12—C11—C9	117.91 (14)	C19—C20—H20B	109.1 (14)
C12—C11—C10	116.07 (14)	H20A—C20—H20B	107 (2)
C9—C11—C10	88.32 (12)