4,5-Bis(phenyl­sulfonyl­thio)-1,3-dithiol­ane-2-thione

The central 1,3-dithiol­ane-2-thione fragment of the title compound, C₁₅H₁₀O₄S₇, is planar; the conformations of the phenyl­sulfonyl­thio substituents in positions 4 and 5 of the dithiol­ane ring are related by an approximate twofold axis coinciding with the C=S bond of the 1,3-dithiol­ane-2-thione group. The planes of the phen­yl rings form dihedral angles of 25.4 (4) and 31.1 (4)° with the least-squares plane of the central dithiol­ane ring.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.014 Å
• R factor = 0.066
• wR factor = 0.185
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         14

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.638     0.835
            Tmin' and Tmax expected:      0.745     0.835
            RR' =      0.856
            Please check that your absorption correction is appropriate.
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         47 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.84
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 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: XSCANS (Bruker,1996); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: program (reference)?.

(I)

Crystal data

C15H10O4S7	F(000) = 976
Mr = 478.65	Dx = 1.614 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.3011 (17) Å	Cell parameters from 61 reflections
b = 12.3846 (13) Å	θ = 5.0–12.4°
c = 14.187 (2) Å	µ = 0.82 mm^−1
β = 114.338 (11)°	T = 293 K
V = 1969.2 (5) Å^3	Prism, yellow
Z = 4	0.35 × 0.31 × 0.22 mm

Data collection

Bruker P4 diffractometer	1760 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.054
Graphite monochromator	θmax = 26.0°, θmin = 1.8°
ω scans	h = −15→1
Absorption correction: ψ scan (XSCANS; Bruker, 1996)	k = −15→1
Tmin = 0.638, Tmax = 0.835	l = −16→17
4637 measured reflections	3 standard reflections every 97 reflections
3768 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.066	H-atom parameters constrained
wR(F^2) = 0.185	w = 1/[σ^2(Fo^2) + (0.02P)^2 + 8.6426P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max < 0.001
3768 reflections	Δρmax = 0.45 e Å^−3
236 parameters	Δρmin = −0.61 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0058 (5)

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
C1	0.2457 (6)	0.0431 (6)	0.7436 (6)	0.0566 (19)
C2	0.2542 (6)	0.2114 (5)	0.6363 (6)	0.0507 (17)
C3	0.2592 (6)	0.1257 (5)	0.5788 (6)	0.0512 (17)
C4	0.0041 (7)	0.2093 (5)	0.3911 (6)	0.0546 (18)
C5	−0.0152 (7)	0.3075 (6)	0.3411 (6)	0.067 (2)
H5A	0.0103	0.3195	0.2887	0.080*
C6	−0.0735 (8)	0.3883 (7)	0.3705 (8)	0.086 (3)
H6A	−0.0903	0.4545	0.3365	0.103*
C7	−0.1064 (9)	0.3681 (8)	0.4520 (9)	0.092 (3)
H7A	−0.1434	0.4226	0.4731	0.111*
C8	−0.0860 (8)	0.2715 (7)	0.5012 (8)	0.078 (3)
H8A	−0.1104	0.2599	0.5543	0.093*
C9	−0.0288 (7)	0.1904 (6)	0.4723 (6)	0.060 (2)
H9A	−0.0127	0.1244	0.5066	0.072*
C10	0.5008 (7)	0.3092 (6)	0.6254 (7)	0.060 (2)
C11	0.5045 (8)	0.3362 (7)	0.5339 (7)	0.069 (2)
H11A	0.4677	0.3989	0.4993	0.083*
C12	0.5636 (9)	0.2693 (8)	0.4930 (8)	0.086 (3)
H12A	0.5686	0.2871	0.4312	0.103*
C13	0.6146 (10)	0.1771 (9)	0.5439 (9)	0.096 (3)
H13A	0.6514	0.1309	0.5143	0.115*
C14	0.6139 (10)	0.1487 (9)	0.6390 (9)	0.101 (3)
H14A	0.6522	0.0866	0.6738	0.121*
C15	0.5540 (8)	0.2165 (7)	0.6798 (8)	0.077 (3)
H15A	0.5497	0.2001	0.7422	0.092*
O1	0.0505 (5)	0.0036 (4)	0.3867 (5)	0.0680 (15)
O2	0.0800 (5)	0.1239 (4)	0.2604 (4)	0.0734 (16)
O3	0.4577 (6)	0.3687 (5)	0.7831 (5)	0.0806 (17)
O4	0.4231 (6)	0.5022 (4)	0.6431 (5)	0.0827 (18)
S1	0.2345 (2)	−0.0353 (2)	0.8307 (2)	0.0842 (8)
S2	0.2488 (2)	0.18389 (17)	0.75328 (18)	0.0681 (6)
S3	0.25720 (19)	−0.00028 (15)	0.63162 (18)	0.0613 (6)
S4	0.26486 (18)	0.13498 (16)	0.45786 (17)	0.0613 (6)
S5	0.08245 (19)	0.10653 (15)	0.35960 (17)	0.0591 (5)
S6	0.24298 (19)	0.34592 (16)	0.59385 (19)	0.0680 (6)
S7	0.4226 (2)	0.39319 (16)	0.67563 (17)	0.0641 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.039 (4)	0.066 (4)	0.066 (5)	0.011 (3)	0.023 (4)	0.008 (4)
C2	0.045 (4)	0.052 (4)	0.056 (4)	0.003 (3)	0.023 (4)	−0.002 (3)
C3	0.046 (4)	0.052 (4)	0.063 (5)	0.003 (3)	0.030 (4)	0.000 (3)
C4	0.058 (5)	0.049 (4)	0.065 (5)	−0.006 (3)	0.033 (4)	0.004 (3)
C5	0.072 (5)	0.069 (5)	0.062 (5)	−0.006 (4)	0.032 (5)	0.014 (4)
C6	0.089 (7)	0.067 (5)	0.105 (8)	0.023 (5)	0.043 (6)	0.033 (5)
C7	0.087 (7)	0.092 (7)	0.106 (9)	0.019 (6)	0.049 (7)	0.013 (6)
C8	0.086 (6)	0.067 (5)	0.103 (8)	−0.004 (5)	0.062 (6)	0.007 (5)
C9	0.065 (5)	0.055 (4)	0.071 (5)	−0.006 (4)	0.039 (5)	0.009 (4)
C10	0.053 (5)	0.056 (4)	0.076 (6)	−0.002 (4)	0.032 (4)	0.003 (4)
C11	0.074 (6)	0.066 (5)	0.066 (6)	−0.014 (4)	0.028 (5)	−0.003 (4)
C12	0.108 (8)	0.090 (7)	0.079 (7)	−0.022 (6)	0.058 (6)	−0.010 (6)
C13	0.101 (8)	0.097 (8)	0.106 (9)	0.013 (6)	0.059 (7)	−0.007 (7)
C14	0.114 (8)	0.093 (7)	0.115 (9)	0.037 (6)	0.064 (8)	0.025 (6)
C15	0.086 (6)	0.072 (6)	0.086 (7)	0.015 (5)	0.049 (6)	0.015 (5)
O1	0.085 (4)	0.047 (3)	0.082 (4)	−0.009 (3)	0.044 (3)	0.010 (3)
O2	0.094 (4)	0.076 (4)	0.061 (4)	−0.023 (3)	0.043 (3)	−0.008 (3)
O3	0.091 (4)	0.088 (4)	0.065 (4)	−0.011 (3)	0.034 (4)	−0.012 (3)
O4	0.107 (5)	0.043 (3)	0.103 (5)	−0.007 (3)	0.048 (4)	0.000 (3)
S1	0.0830 (17)	0.0954 (17)	0.0823 (17)	0.0036 (14)	0.0421 (14)	0.0269 (14)
S2	0.0757 (14)	0.0637 (12)	0.0784 (15)	0.0091 (11)	0.0455 (13)	−0.0024 (11)
S3	0.0655 (13)	0.0492 (10)	0.0775 (14)	0.0004 (9)	0.0378 (11)	−0.0005 (9)
S4	0.0642 (12)	0.0657 (12)	0.0695 (13)	−0.0066 (10)	0.0432 (11)	−0.0053 (10)
S5	0.0714 (13)	0.0509 (10)	0.0666 (13)	−0.0126 (9)	0.0401 (11)	−0.0029 (9)
S6	0.0655 (13)	0.0505 (11)	0.0899 (17)	0.0074 (10)	0.0340 (12)	0.0019 (10)
S7	0.0758 (14)	0.0500 (11)	0.0705 (14)	−0.0047 (10)	0.0342 (12)	−0.0038 (9)

Geometric parameters (Å, º)

C1—S1	1.622 (7)	C9—H9A	0.9300
C1—S3	1.736 (8)	C10—C11	1.360 (11)
C1—S2	1.749 (8)	C10—C15	1.388 (11)
C2—C3	1.355 (9)	C10—S7	1.755 (8)
C2—S2	1.722 (7)	C11—C12	1.378 (11)
C2—S6	1.758 (7)	C11—H11A	0.9300
C3—S3	1.735 (7)	C12—C13	1.359 (13)
C3—S4	1.750 (7)	C12—H12A	0.9300
C4—C5	1.379 (10)	C13—C14	1.397 (14)
C4—C9	1.389 (10)	C13—H13A	0.9300
C4—S5	1.762 (7)	C14—C15	1.391 (11)
C5—C6	1.392 (11)	C14—H14A	0.9300
C5—H5A	0.9300	C15—H15A	0.9300
C6—C7	1.396 (13)	O1—S5	1.433 (5)
C6—H6A	0.9300	O2—S5	1.412 (5)
C7—C8	1.356 (12)	O3—S7	1.435 (6)
C7—H7A	0.9300	O4—S7	1.427 (5)
C8—C9	1.382 (10)	S4—S5	2.127 (3)
C8—H8A	0.9300	S6—S7	2.111 (3)
S1—C1—S3	125.2 (5)	C10—C11—H11A	120.5
S1—C1—S2	122.8 (5)	C12—C11—H11A	120.5
S3—C1—S2	111.9 (4)	C13—C12—C11	119.3 (9)
C3—C2—S2	117.0 (5)	C13—C12—H12A	120.4
C3—C2—S6	123.6 (6)	C11—C12—H12A	120.4
S2—C2—S6	119.3 (4)	C12—C13—C14	122.7 (9)
C2—C3—S3	115.6 (5)	C12—C13—H13A	118.7
C2—C3—S4	124.7 (6)	C14—C13—H13A	118.7
S3—C3—S4	119.7 (4)	C15—C14—C13	117.7 (9)
C5—C4—C9	121.9 (7)	C15—C14—H14A	121.1
C5—C4—S5	120.1 (6)	C13—C14—H14A	121.1
C9—C4—S5	117.8 (6)	C10—C15—C14	118.5 (8)
C4—C5—C6	118.7 (7)	C10—C15—H15A	120.8
C4—C5—H5A	120.7	C14—C15—H15A	120.8
C6—C5—H5A	120.7	C2—S2—C1	97.4 (3)
C5—C6—C7	118.8 (8)	C3—S3—C1	97.9 (3)
C5—C6—H6A	120.6	C3—S4—S5	100.0 (2)
C7—C6—H6A	120.6	O2—S5—O1	120.5 (3)
C8—C7—C6	122.0 (9)	O2—S5—C4	110.7 (4)
C8—C7—H7A	119.0	O1—S5—C4	109.6 (3)
C6—C7—H7A	119.0	O2—S5—S4	102.2 (3)
C7—C8—C9	119.8 (8)	O1—S5—S4	107.7 (3)
C7—C8—H8A	120.1	C4—S5—S4	104.7 (3)
C9—C8—H8A	120.1	C2—S6—S7	99.1 (3)
C8—C9—C4	118.8 (7)	O4—S7—O3	120.3 (4)
C8—C9—H9A	120.6	O4—S7—C10	110.7 (4)
C4—C9—H9A	120.6	O3—S7—C10	109.3 (4)
C11—C10—C15	122.7 (8)	O4—S7—S6	103.2 (3)
C11—C10—S7	118.8 (6)	O3—S7—S6	108.3 (3)
C15—C10—S7	118.4 (6)	C10—S7—S6	103.7 (3)
C10—C11—C12	119.1 (9)
S2—C2—C3—S3	0.8 (8)	S4—C3—S3—C1	−177.8 (4)
S6—C2—C3—S3	−174.7 (4)	S1—C1—S3—C3	177.7 (5)
S2—C2—C3—S4	179.8 (4)	S2—C1—S3—C3	−2.8 (5)
S6—C2—C3—S4	4.3 (10)	C2—C3—S4—S5	−99.1 (6)
C9—C4—C5—C6	−2.5 (13)	S3—C3—S4—S5	79.8 (4)
S5—C4—C5—C6	−177.7 (7)	C5—C4—S5—O2	−21.2 (8)
C4—C5—C6—C7	2.3 (14)	C9—C4—S5—O2	163.5 (6)
C5—C6—C7—C8	−1.8 (17)	C5—C4—S5—O1	−156.4 (7)
C6—C7—C8—C9	1.4 (17)	C9—C4—S5—O1	28.3 (8)
C7—C8—C9—C4	−1.5 (14)	C5—C4—S5—S4	88.3 (7)
C5—C4—C9—C8	2.1 (12)	C9—C4—S5—S4	−87.0 (6)
S5—C4—C9—C8	177.4 (7)	C3—S4—S5—O2	174.3 (3)
C15—C10—C11—C12	−0.2 (13)	C3—S4—S5—O1	−57.8 (3)
S7—C10—C11—C12	−178.6 (7)	C3—S4—S5—C4	58.8 (3)
C10—C11—C12—C13	1.3 (14)	C3—C2—S6—S7	−101.5 (6)
C11—C12—C13—C14	−2.7 (17)	S2—C2—S6—S7	83.0 (4)
C12—C13—C14—C15	2.7 (18)	C11—C10—S7—O4	−28.9 (8)
C11—C10—C15—C14	0.2 (14)	C15—C10—S7—O4	152.5 (7)
S7—C10—C15—C14	178.7 (8)	C11—C10—S7—O3	−163.6 (6)
C13—C14—C15—C10	−1.4 (16)	C15—C10—S7—O3	17.9 (8)
C3—C2—S2—C1	−2.5 (6)	C11—C10—S7—S6	81.1 (7)
S6—C2—S2—C1	173.3 (4)	C15—C10—S7—S6	−97.4 (7)
S1—C1—S2—C2	−177.3 (5)	C2—S6—S7—O4	178.2 (4)
S3—C1—S2—C2	3.1 (5)	C2—S6—S7—O3	−53.3 (4)
C2—C3—S3—C1	1.2 (6)	C2—S6—S7—C10	62.8 (4)