1,6-Bis(phenyl­sulfan­yl)hexa­ne

The title compound, C₁₆H₁₈S₂ (or L⁶), crystallizes with two half-mol­ecules in the asymmetric unit and each independent mol­ecule lies about a crystallographic center of symmetry. The aliphatic segment of this ligand is in an all-trans conformation.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.036
• wR factor = 0.068
• Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.663
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         41 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   2 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: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: local Program; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: UdMX (local program).

1,6-Bis(phenylsulfanyl)hexane

Crystal data

C18H22S2	Z = 2
Mr = 302.48	F(000) = 324
Triclinic, P1	Dx = 1.233 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 5.627 (2) Å	Cell parameters from 25 reflections
b = 7.862 (3) Å	θ = 20.0–25.0°
c = 18.486 (6) Å	µ = 2.84 mm^−1
α = 94.55 (3)°	T = 298 K
β = 91.36 (3)°	Platelet, colorless
γ = 90.46 (3)°	0.23 × 0.15 × 0.02 mm
V = 815.0 (5) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	1270 reflections with I > 2σ(I)
Radiation source: X-ray sealed tube	Rint = 0.059
Graphite monochromator	θmax = 69.8°, θmin = 2.4°
ω scans	h = −6→6
Absorption correction: gaussian from crystal shape	k = −9→9
Tmin = 0.560, Tmax = 0.940	l = −22→22
25176 measured reflections	5 standard reflections every 60 min
3086 independent reflections	intensity decay: 0.03%

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.068	H-atom parameters constrained
S = 0.66	w = 1/[σ^2(Fo^2) + (0.0003P)^2] where P = (Fo^2 + 2Fc^2)/3
3086 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.25 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	0.53505 (18)	0.43816 (12)	0.19100 (5)	0.0541 (3)
S2	−0.02359 (18)	0.10379 (12)	0.81264 (5)	0.0550 (3)
C11	0.5038 (6)	0.3818 (4)	0.28080 (18)	0.0380 (9)
C12	0.6791 (6)	0.4380 (4)	0.33127 (18)	0.0468 (9)
H12	0.8062	0.5026	0.3168	0.056*
C13	0.6676 (7)	0.3993 (4)	0.40260 (19)	0.0561 (10)
H13	0.7867	0.4374	0.4359	0.067*
C14	0.4797 (7)	0.3044 (4)	0.4245 (2)	0.0530 (11)
H14	0.4712	0.2788	0.4727	0.064*
C15	0.3050 (6)	0.2477 (4)	0.37524 (18)	0.0499 (10)
H15	0.1783	0.1834	0.3902	0.060*
C16	0.3155 (6)	0.2852 (4)	0.30332 (17)	0.0448 (9)
H16	0.1966	0.2458	0.2702	0.054*
C17	0.2411 (6)	0.4137 (4)	0.15052 (17)	0.0477 (10)
H17A	0.1941	0.2943	0.1466	0.057*
H17B	0.1280	0.4770	0.1807	0.057*
C18	0.2419 (7)	0.4804 (4)	0.07560 (18)	0.0510 (10)
H18A	0.2929	0.5990	0.0801	0.061*
H18B	0.3560	0.4165	0.0461	0.061*
C19	0.0008 (7)	0.4667 (4)	0.03759 (17)	0.0490 (10)
H19A	−0.1132	0.5304	0.0672	0.059*
H19B	−0.0500	0.3480	0.0331	0.059*
C21	0.0013 (6)	0.1337 (4)	0.71941 (18)	0.0381 (9)
C22	−0.1808 (6)	0.2228 (4)	0.68801 (18)	0.0438 (9)
H22	−0.3041	0.2662	0.7163	0.053*
C23	−0.1796 (6)	0.2472 (4)	0.61519 (18)	0.0497 (10)
H23	−0.3031	0.3064	0.5946	0.060*
C24	0.0026 (7)	0.1850 (4)	0.5723 (2)	0.0531 (11)
H24	0.0028	0.2020	0.5231	0.064*
C25	0.1846 (6)	0.0970 (4)	0.60347 (17)	0.0489 (9)
H25	0.3080	0.0546	0.5749	0.059*
C26	0.1860 (6)	0.0713 (4)	0.67650 (17)	0.0433 (9)
H26	0.3100	0.0124	0.6969	0.052*
C27	0.2719 (6)	0.0575 (4)	0.84401 (18)	0.0494 (10)
H27A	0.3251	−0.0496	0.8204	0.059*
H27B	0.3814	0.1471	0.8328	0.059*
C28	0.2646 (7)	0.0459 (4)	0.92555 (19)	0.0525 (11)
H28A	0.2086	0.1533	0.9481	0.063*
H28B	0.1513	−0.0423	0.9356	0.063*
C29	0.5031 (7)	0.0063 (5)	0.95945 (17)	0.0523 (10)
H29A	0.6161	0.0948	0.9495	0.063*
H29B	0.5594	−0.1008	0.9367	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0490 (7)	0.0737 (7)	0.0412 (6)	−0.0039 (5)	0.0037 (5)	0.0153 (5)
S2	0.0480 (7)	0.0815 (8)	0.0366 (6)	0.0043 (5)	−0.0020 (5)	0.0123 (5)
C11	0.042 (2)	0.035 (2)	0.037 (2)	0.0048 (16)	−0.0012 (18)	0.0044 (15)
C12	0.038 (2)	0.049 (2)	0.054 (2)	−0.0042 (17)	−0.0024 (18)	0.0079 (18)
C13	0.061 (3)	0.055 (3)	0.051 (2)	−0.002 (2)	−0.021 (2)	0.0068 (19)
C14	0.068 (3)	0.055 (3)	0.037 (2)	0.003 (2)	−0.004 (2)	0.0099 (18)
C15	0.052 (3)	0.058 (2)	0.042 (2)	−0.0073 (19)	0.0012 (18)	0.0115 (18)
C16	0.045 (2)	0.051 (2)	0.0380 (19)	−0.0079 (18)	−0.0079 (17)	0.0060 (17)
C17	0.053 (3)	0.055 (2)	0.036 (2)	−0.0010 (19)	−0.0032 (19)	0.0070 (18)
C18	0.065 (3)	0.055 (2)	0.034 (2)	0.000 (2)	0.003 (2)	0.0117 (18)
C19	0.058 (3)	0.059 (2)	0.032 (2)	−0.0005 (19)	0.0030 (19)	0.0102 (17)
C21	0.044 (2)	0.036 (2)	0.034 (2)	−0.0076 (16)	−0.0054 (18)	0.0050 (15)
C22	0.037 (2)	0.048 (2)	0.045 (2)	0.0043 (17)	−0.0024 (17)	−0.0006 (18)
C23	0.053 (3)	0.053 (2)	0.044 (2)	0.0049 (19)	−0.0142 (18)	0.0104 (18)
C24	0.070 (3)	0.053 (3)	0.037 (2)	−0.011 (2)	−0.007 (2)	0.0083 (18)
C25	0.052 (2)	0.057 (2)	0.038 (2)	0.0031 (19)	0.0072 (18)	0.0040 (18)
C26	0.043 (2)	0.046 (2)	0.042 (2)	0.0067 (17)	−0.0025 (17)	0.0078 (17)
C27	0.058 (3)	0.057 (2)	0.034 (2)	0.0063 (19)	−0.0062 (19)	0.0101 (18)
C28	0.060 (3)	0.061 (3)	0.037 (2)	0.003 (2)	−0.007 (2)	0.0119 (18)
C29	0.061 (3)	0.063 (2)	0.034 (2)	0.0085 (19)	−0.008 (2)	0.0101 (19)

Geometric parameters (Å, º)

S1—C11	1.764 (3)	C19—H19a	0.97
S1—C17	1.802 (3)	C19—H19b	0.97
S2—C21	1.766 (3)	C21—C26	1.391 (4)
S2—C27	1.798 (3)	C21—C22	1.388 (4)
C11—C16	1.390 (4)	C22—C23	1.375 (4)
C11—C12	1.387 (4)	C22—H22	0.93
C12—C13	1.379 (4)	C23—C24	1.380 (4)
C12—H12	0.93	C23—H23	0.93
C13—C14	1.377 (4)	C24—C25	1.381 (4)
C13—H13	0.93	C24—H24	0.93
C14—C15	1.372 (4)	C25—C26	1.381 (4)
C14—H14	0.93	C25—H25	0.93
C15—C16	1.387 (4)	C26—H26	0.93
C15—H15	0.93	C27—C28	1.519 (4)
C16—H16	0.93	C27—H27a	0.97
C17—C18	1.519 (4)	C27—H27b	0.97
C17—H17a	0.97	C28—C29	1.513 (4)
C17—H17b	0.97	C28—H28a	0.97
C18—C19	1.512 (4)	C28—H28b	0.97
C18—H18a	0.97	C29—C29^ii	1.512 (6)
C18—H18b	0.97	C29—H29a	0.97
C19—C19^i	1.524 (6)	C29—H29b	0.97
C11—S1—C17	104.78 (17)	H19A—C19—H19B	107.7
C21—S2—C27	105.51 (17)	C26—C21—C22	119.2 (3)
C16—C11—C12	118.8 (3)	C26—C21—S2	124.4 (3)
C16—C11—S1	123.9 (3)	C22—C21—S2	116.4 (3)
C12—C11—S1	117.3 (3)	C23—C22—C21	120.3 (3)
C11—C12—C13	120.9 (3)	C23—C22—H22	119.9
C11—C12—H12	119.6	C21—C22—H22	119.9
C13—C12—H12	119.6	C24—C23—C22	120.8 (3)
C14—C13—C12	120.0 (3)	C24—C23—H23	119.6
C14—C13—H13	120	C22—C23—H23	119.6
C12—C13—H13	120	C23—C24—C25	119.0 (3)
C13—C14—C15	119.9 (3)	C23—C24—H24	120.5
C13—C14—H14	120.1	C25—C24—H24	120.5
C15—C14—H14	120.1	C24—C25—C26	120.9 (3)
C14—C15—C16	120.6 (3)	C24—C25—H25	119.6
C14—C15—H15	119.7	C26—C25—H25	119.6
C16—C15—H15	119.7	C21—C26—C25	119.8 (3)
C11—C16—C15	119.9 (3)	C21—C26—H26	120.1
C11—C16—H16	120	C25—C26—H26	120.1
C15—C16—H16	120	C28—C27—S2	107.7 (3)
C18—C17—S1	109.0 (3)	C28—C27—H27A	110.2
C18—C17—H17A	109.9	S2—C27—H27A	110.2
S1—C17—H17A	109.9	C28—C27—H27B	110.2
C18—C17—H17B	109.9	S2—C27—H27B	110.2
S1—C17—H17B	109.9	H27A—C27—H27B	108.5
H17A—C17—H17B	108.3	C29—C28—C27	113.4 (3)
C19—C18—C17	112.8 (3)	C29—C28—H28A	108.9
C19—C18—H18A	109	C27—C28—H28A	108.9
C17—C18—H18A	109	C29—C28—H28B	108.9
C19—C18—H18B	109	C27—C28—H28B	108.9
C17—C18—H18B	109	H28A—C28—H28B	107.7
H18A—C18—H18B	107.8	C28—C29—C29^ii	113.7 (4)
C18—C19—C19^i	113.3 (4)	C28—C29—H29A	108.8
C18—C19—H19A	108.9	C29^ii—C29—H29A	108.8
C19^i—C19—H19A	108.9	C28—C29—H29B	108.8
C18—C19—H19B	108.9	C29^ii—C29—H29B	108.8
C19^i—C19—H19B	108.9	H29A—C29—H29B	107.7
C17—S1—C11—C16	19.8 (3)	C27—S2—C21—C26	21.4 (3)
C17—S1—C11—C12	−160.3 (3)	C27—S2—C21—C22	−160.0 (2)
C16—C11—C12—C13	−0.1 (5)	C26—C21—C22—C23	0.7 (5)
S1—C11—C12—C13	180.0 (3)	S2—C21—C22—C23	−177.9 (2)
C11—C12—C13—C14	−0.3 (5)	C21—C22—C23—C24	−0.5 (5)
C12—C13—C14—C15	0.4 (6)	C22—C23—C24—C25	0.1 (5)
C13—C14—C15—C16	−0.1 (6)	C23—C24—C25—C26	−0.1 (5)
C12—C11—C16—C15	0.4 (5)	C22—C21—C26—C25	−0.7 (5)
S1—C11—C16—C15	−179.7 (3)	S2—C21—C26—C25	177.9 (2)
C14—C15—C16—C11	−0.3 (5)	C24—C25—C26—C21	0.3 (5)
C11—S1—C17—C18	173.0 (2)	C21—S2—C27—C28	175.1 (2)
S1—C17—C18—C19	−179.4 (2)	S2—C27—C28—C29	179.7 (2)
C17—C18—C19—C19^i	179.9 (4)	C27—C28—C29—C29^ii	−179.7 (4)

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y, −z+2.