4,4'-Bis[(phenyl­sulfan­yl)meth­yl]biphen­yl

The title compound, C₂₆H₂₂S₂, was obtained by the reaction of 4,4'-bis­(chloro­meth­yl)biphenyl with the sodium salt of thio­phenol in ethanol. The mol­ecule has an inversion centre, with the two phenyl fragments in the same plane.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.098
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

4,4'-Bis[(phenylsulfanyl)methyl]biphenyl

Crystal data

C26H22S2	F(000) = 420
Mr = 398.58	Dx = 1.288 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2236 reflections
a = 23.2051 (6) Å	θ = 2.8–27.2°
b = 5.5097 (1) Å	µ = 0.27 mm^−1
c = 8.0412 (2) Å	T = 273 K
β = 91.216 (2)°	Block, yellow
V = 1027.86 (4) Å^3	0.24 × 0.22 × 0.22 mm
Z = 2

Data collection

Bruker APEX-II CCD area-detector diffractometer	1815 independent reflections
Radiation source: fine-focus sealed tube	1393 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −27→27
Tmin = 0.939, Tmax = 0.943	k = −6→6
8768 measured reflections	l = −9→9

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) = 0.098	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0466P)^2 + 0.2242P] where P = (Fo^2 + 2Fc^2)/3
1815 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.28 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	0.25427 (2)	0.41294 (11)	0.51269 (7)	0.0709 (2)
C1	0.36717 (8)	0.2979 (4)	0.5314 (2)	0.0598 (5)
H1	0.3561	0.1653	0.4667	0.072*
C2	0.42443 (8)	0.3292 (4)	0.5754 (3)	0.0662 (5)
H2	0.4517	0.2187	0.5391	0.079*
C3	0.44141 (8)	0.5220 (4)	0.6725 (3)	0.0657 (5)
H3	0.4800	0.5421	0.7027	0.079*
C4	0.40099 (8)	0.6848 (4)	0.7245 (3)	0.0651 (5)
H4	0.4124	0.8154	0.7907	0.078*
C5	0.34362 (8)	0.6577 (4)	0.6801 (2)	0.0605 (5)
H5	0.3167	0.7704	0.7156	0.073*
C6	0.32609 (7)	0.4622 (3)	0.5825 (2)	0.0514 (4)
C7	0.21186 (8)	0.5731 (4)	0.6624 (2)	0.0642 (5)
H7A	0.2189	0.5064	0.7726	0.077*
H7B	0.2225	0.7433	0.6642	0.077*
C8	0.14923 (7)	0.5469 (4)	0.6145 (2)	0.0534 (5)
C9	0.12224 (8)	0.7195 (4)	0.5163 (2)	0.0635 (5)
H9	0.1434	0.8515	0.4791	0.076*
C10	0.06477 (8)	0.7013 (4)	0.4718 (2)	0.0609 (5)
H10	0.0481	0.8213	0.4052	0.073*
C11	0.03111 (6)	0.5090 (3)	0.52348 (18)	0.0431 (4)
C12	0.05883 (8)	0.3358 (3)	0.6225 (2)	0.0579 (5)
H12	0.0378	0.2037	0.6602	0.069*
C13	0.11630 (8)	0.3538 (4)	0.6664 (2)	0.0625 (5)
H13	0.1333	0.2336	0.7322	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0466 (3)	0.0942 (5)	0.0718 (4)	−0.0005 (2)	−0.0026 (2)	−0.0276 (3)
C1	0.0575 (11)	0.0615 (12)	0.0603 (11)	0.0033 (9)	−0.0011 (9)	−0.0077 (9)
C2	0.0540 (11)	0.0742 (14)	0.0705 (13)	0.0125 (10)	0.0020 (9)	−0.0006 (11)
C3	0.0435 (10)	0.0826 (15)	0.0707 (13)	−0.0027 (10)	−0.0035 (9)	0.0081 (11)
C4	0.0572 (12)	0.0665 (13)	0.0713 (13)	−0.0103 (10)	−0.0025 (9)	−0.0070 (10)
C5	0.0499 (11)	0.0618 (12)	0.0699 (12)	0.0013 (9)	0.0027 (9)	−0.0094 (10)
C6	0.0456 (9)	0.0585 (11)	0.0501 (10)	−0.0002 (8)	0.0016 (7)	−0.0005 (8)
C7	0.0480 (10)	0.0848 (15)	0.0596 (11)	0.0042 (10)	−0.0051 (8)	−0.0136 (10)
C8	0.0451 (10)	0.0681 (12)	0.0469 (10)	0.0048 (9)	−0.0016 (7)	−0.0088 (9)
C9	0.0496 (11)	0.0715 (13)	0.0695 (12)	−0.0100 (9)	0.0036 (9)	0.0121 (10)
C10	0.0501 (11)	0.0670 (12)	0.0654 (12)	−0.0009 (9)	−0.0048 (9)	0.0201 (10)
C11	0.0441 (9)	0.0467 (9)	0.0386 (8)	0.0013 (7)	0.0020 (7)	−0.0042 (7)
C12	0.0536 (11)	0.0532 (11)	0.0665 (12)	−0.0027 (8)	−0.0080 (9)	0.0105 (9)
C13	0.0579 (11)	0.0617 (12)	0.0673 (12)	0.0076 (9)	−0.0150 (9)	0.0078 (10)

Geometric parameters (Å, º)

S1—C6	1.7682 (17)	C7—H7A	0.9700
S1—C7	1.8015 (19)	C7—H7B	0.9700
C1—C2	1.379 (3)	C8—C9	1.378 (3)
C1—C6	1.383 (2)	C8—C13	1.380 (3)
C1—H1	0.9300	C9—C10	1.377 (2)
C2—C3	1.371 (3)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.386 (2)
C3—C4	1.370 (3)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.392 (2)
C4—C5	1.379 (2)	C11—C11^i	1.488 (3)
C4—H4	0.9300	C12—C13	1.376 (2)
C5—C6	1.389 (3)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C7—C8	1.503 (2)
C6—S1—C7	103.72 (8)	C8—C7—H7B	109.9
C2—C1—C6	120.55 (18)	S1—C7—H7B	109.9
C2—C1—H1	119.7	H7A—C7—H7B	108.3
C6—C1—H1	119.7	C9—C8—C13	117.22 (16)
C3—C2—C1	120.44 (18)	C9—C8—C7	120.40 (18)
C3—C2—H2	119.8	C13—C8—C7	122.37 (17)
C1—C2—H2	119.8	C10—C9—C8	121.64 (18)
C4—C3—C2	119.42 (18)	C10—C9—H9	119.2
C4—C3—H3	120.3	C8—C9—H9	119.2
C2—C3—H3	120.3	C9—C10—C11	121.79 (17)
C3—C4—C5	120.90 (19)	C9—C10—H10	119.1
C3—C4—H4	119.6	C11—C10—H10	119.1
C5—C4—H4	119.6	C10—C11—C12	116.06 (16)
C4—C5—C6	119.99 (17)	C10—C11—C11^i	121.66 (19)
C4—C5—H5	120.0	C12—C11—C11^i	122.28 (19)
C6—C5—H5	120.0	C13—C12—C11	122.08 (17)
C1—C6—C5	118.70 (16)	C13—C12—H12	119.0
C1—C6—S1	117.12 (14)	C11—C12—H12	119.0
C5—C6—S1	124.16 (14)	C12—C13—C8	121.21 (17)
C8—C7—S1	108.72 (12)	C12—C13—H13	119.4
C8—C7—H7A	109.9	C8—C13—H13	119.4
S1—C7—H7A	109.9
C6—C1—C2—C3	0.8 (3)	S1—C7—C8—C13	87.59 (19)
C1—C2—C3—C4	−0.4 (3)	C13—C8—C9—C10	0.2 (3)
C2—C3—C4—C5	−0.3 (3)	C7—C8—C9—C10	−179.39 (18)
C3—C4—C5—C6	0.6 (3)	C8—C9—C10—C11	0.1 (3)
C2—C1—C6—C5	−0.5 (3)	C9—C10—C11—C12	−0.1 (3)
C2—C1—C6—S1	177.55 (15)	C9—C10—C11—C11^i	179.41 (19)
C4—C5—C6—C1	−0.2 (3)	C10—C11—C12—C13	−0.1 (3)
C4—C5—C6—S1	−178.08 (15)	C11^i—C11—C12—C13	−179.63 (19)
C7—S1—C6—C1	157.80 (15)	C11—C12—C13—C8	0.4 (3)
C7—S1—C6—C5	−24.25 (19)	C9—C8—C13—C12	−0.4 (3)
C6—S1—C7—C8	179.28 (14)	C7—C8—C13—C12	179.16 (18)
S1—C7—C8—C9	−92.85 (19)

Symmetry code: (i) −x, −y+1, −z+1.