Dibenzyl sulfide at 150 K

The mol­ecule of the title compound, C₁₄H₁₄S, lies on a crystallographic twofold axis running through the central S atom, and hence mol­ecules have exact C₂ mol­ecular symmetry. Density-functional theory calculations reveal that the energy-optimized mol­ecular structure in the gas phase is close to that observed in the crystal structure. The crystal packing is dominated by double chains running along the c axis formed by C—H...S inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.119
• Data-to-parameter ratio = 29.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.17

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

   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: enCIFer (Version 1.1; Allen et al., 2004).

'Dibenzyl sulfide'

Crystal data

C14H14S	F(000) = 456
Mr = 214.31	Dx = 1.238 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 6732 reflections
a = 13.9913 (12) Å	θ = 2.3–32.8°
b = 11.3985 (8) Å	µ = 0.24 mm^−1
c = 7.2081 (5) Å	T = 150 K
V = 1149.55 (15) Å^3	Prism, colourless
Z = 4	0.22 × 0.20 × 0.16 mm

Data collection

Oxford Diffraction XCALIBUR3 diffractometer	2020 independent reflections
Radiation source: Sealed tube	1541 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω scans	θmax = 32.8°, θmin = 2.3°
Absorption correction: numerical (CrysAlis RED; Oxford Diffraction, 2006)	h = −20→21
Tmin = 0.944, Tmax = 0.969	k = −15→17
10614 measured reflections	l = −9→10

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	Only H-atom coordinates refined
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0676P)^2 + 0.1503P] where P = (Fo^2 + 2Fc^2)/3
2020 reflections	(Δ/σ)max < 0.001
69 parameters	Δρmax = 0.48 e Å^−3
0 restraints	Δρmin = −0.22 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
S1	0.5000	0.40793 (3)	0.2500	0.02939 (13)
C3	0.63352 (8)	0.30536 (10)	−0.11031 (15)	0.0306 (2)
C1	0.47682 (8)	0.30718 (11)	0.06122 (16)	0.0313 (2)
C2	0.56389 (7)	0.24483 (9)	−0.01006 (14)	0.0269 (2)
C4	0.71193 (8)	0.24727 (12)	−0.18304 (16)	0.0341 (3)
C7	0.57683 (8)	0.12541 (10)	0.01948 (16)	0.0332 (2)
C5	0.72322 (8)	0.12790 (12)	−0.15511 (17)	0.0352 (3)
C6	0.65572 (9)	0.06698 (11)	−0.05254 (17)	0.0372 (3)
H4	0.7564 (13)	0.2873 (17)	−0.256 (2)	0.054 (5)*
H1B	0.4277 (10)	0.2510 (14)	0.096 (2)	0.040 (4)*
H7	0.5289 (13)	0.0817 (13)	0.094 (3)	0.049 (5)*
H5	0.7774 (14)	0.0880 (15)	−0.209 (3)	0.051 (5)*
H3	0.6261 (12)	0.3886 (15)	−0.127 (2)	0.050 (4)*
H1A	0.4477 (12)	0.3543 (15)	−0.037 (2)	0.048 (4)*
H6	0.6640 (13)	−0.0166 (17)	−0.032 (2)	0.054 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0273 (2)	0.0273 (2)	0.0336 (2)	0.000	0.00058 (13)	0.000
C3	0.0270 (5)	0.0368 (5)	0.0279 (5)	−0.0005 (4)	−0.0009 (4)	0.0075 (4)
C1	0.0223 (4)	0.0433 (6)	0.0282 (5)	−0.0016 (4)	−0.0022 (4)	−0.0022 (5)
C2	0.0223 (4)	0.0372 (5)	0.0214 (4)	−0.0045 (4)	−0.0019 (3)	−0.0023 (4)
C4	0.0258 (5)	0.0484 (7)	0.0279 (5)	−0.0034 (4)	0.0025 (4)	0.0052 (5)
C7	0.0348 (5)	0.0336 (5)	0.0312 (5)	−0.0108 (4)	0.0048 (4)	−0.0056 (4)
C5	0.0295 (5)	0.0449 (6)	0.0312 (5)	0.0014 (5)	0.0013 (4)	−0.0071 (5)
C6	0.0414 (6)	0.0323 (5)	0.0378 (6)	−0.0038 (5)	0.0032 (5)	−0.0071 (5)

Geometric parameters (Å, º)

S1—C1	1.8098 (12)	C2—C7	1.3896 (16)
S1—C1^i	1.8098 (12)	C4—C5	1.3845 (19)
C3—C4	1.3844 (16)	C4—H4	0.936 (18)
C3—C2	1.3955 (14)	C7—C6	1.3898 (17)
C3—H3	0.963 (16)	C7—H7	0.992 (18)
C1—C2	1.5010 (15)	C5—C6	1.3859 (18)
C1—H1B	0.971 (15)	C5—H5	0.964 (19)
C1—H1A	0.978 (17)	C6—H6	0.971 (19)
C1—S1—C1^i	101.23 (8)	C3—C4—C5	120.36 (11)
C4—C3—C2	120.85 (11)	C3—C4—H4	120.5 (12)
C4—C3—H3	120.7 (10)	C5—C4—H4	119.1 (12)
C2—C3—H3	118.5 (10)	C2—C7—C6	121.05 (10)
C2—C1—S1	114.35 (7)	C2—C7—H7	119.1 (10)
C2—C1—H1B	110.5 (9)	C6—C7—H7	119.8 (10)
S1—C1—H1B	110.6 (9)	C4—C5—C6	119.49 (11)
C2—C1—H1A	110.5 (10)	C4—C5—H5	119.7 (10)
S1—C1—H1A	105.7 (10)	C6—C5—H5	120.9 (11)
H1B—C1—H1A	104.6 (13)	C5—C6—C7	120.02 (12)
C7—C2—C3	118.21 (10)	C5—C6—H6	119.5 (10)
C7—C2—C1	121.14 (10)	C7—C6—H6	120.5 (10)
C3—C2—C1	120.65 (10)
C1^i—S1—C1—C2	−72.49 (8)	C3—C2—C7—C6	−1.55 (16)
C4—C3—C2—C7	1.88 (16)	C1—C2—C7—C6	177.58 (10)
C4—C3—C2—C1	−177.25 (10)	C3—C4—C5—C6	−0.45 (18)
S1—C1—C2—C7	110.24 (11)	C4—C5—C6—C7	0.79 (18)
S1—C1—C2—C3	−70.65 (12)	C2—C7—C6—C5	0.23 (18)
C2—C3—C4—C5	−0.90 (17)

Symmetry code: (i) −x+1, y, −z+1/2.