Bis(N-isopropyl-N-phenyl­thio­carbamo­yl) disulfide

Raya, I.; Baba, I.; Rosli, F.Z.; Yamin, B.M.

doi:10.1107/S1600536805026838

Bis(N-isopropyl-N-phenylthiocarbamoyl) disulfide

I. Raya, I. Baba, F. Z. Rosli and B. M. Yamin

The NCS₂ groups in the title compound, C₂₀H₂₃N₂S₄, are approximately perpendicular to each other, forming a dihedral angle of 80.10 (7)°. The S-S bond length is 2.0086 (14) Å and the distance between the two terminal S atoms is 3.940 (3) Å.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805026838/tk6254sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805026838/tk6254Isup2.hkl Contains datablock I

CCDC reference: 287733

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R factor = 0.041
wR factor = 0.125
Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          1

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.54 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT301_ALERT_3_C Main Residue  Disorder .........................       4.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      28.40 Deg.
              C13' -C12  -C13     1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 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
   5 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

Comment top

Some metal–dithiocarbamate complexes are not stable in solution and, upon recrystallization, lead to the formation of decomposition products. One such example is dipyrrolidinylthiuram disulfide, which was obtained from the recrystallization of [Fe{S₂CN(CH₂)₄}₃] from methanol solution (Yamin et al., 1996). Similarly, the title compound, (I), was obtained after recrystallization from a chloroform solution of [Eu(S₂NC₁₀H₁₃)₃(1,10-phenanthroline)].

The molecular structure of (I), Fig. 1, is isostructural with other thiuram disulfides, such as tetraethylthiuram disulfide (Karle et al., 1967) and bis(N-methyl,N-phenyl-thiocarbamoyl)disulfide (Fun et al., 2001). The S—S, C10—S2, C10—S1, C11—S3 and C11—S4 bond distances in (I) are in agreement with these thiuram disulfides (Table 1). However, the C10—S2—S3—C11 torsion angle of 78.70 (13)° is smaller than the value of approximately 96° observed in tetraethylthiuram disulfide (Karle et al., 1967).

Each of the S3/S4/N2/C11/C15 and S1/S2/N1/C7/C10 fragments is planar, with the maximum deviation for either of these being 0.027 (2) Å for atom N1. The dihedral angle between the two least-squares planes through these groups is 80.10 (7)°. The two phenyl groups, C1–C6 and C15–C20, are inclined to each other by 67.70 (15)°.

The molecule of (I) is stablized by intramolecular interactions, with C7—H7···S1 2.59 Å [C7···S1 is 3.068 (4) Å], and the angle subtended at the H atom is 110°.

Experimental top

The starting Eu(C₁₀H₁₂NS₂)₃(1,10-phenanthroline)] complex was prepared following the method described by Su et al. (1995). Recrystallization of this complex from chloroform solution yielded crystals of (I) (m.p. 416–418 K).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top

Fig. 1. The molecular structure of (I), with 50% probability displacement ellipsoids. The dashed line denotes a C—H···S hydrogen bond (see Comment). Only the major disordered component of C13 is shown.

Bis(N-isopropyl-N-phenylthiocarbamoyl) disulfide top

Crystal data top

C₂₀H₂₃N₂S₄	Z = 2
M_r = 419.64	F(000) = 442
Triclinic, P1	D_x = 1.267 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.911 (7) Å	Cell parameters from 3456 reflections
b = 11.568 (9) Å	θ = 1.8–25.0°
c = 12.595 (10) Å	µ = 0.44 mm⁻¹
α = 113.744 (11)°	T = 298 K
β = 97.157 (14)°	Block, colourless
γ = 106.082 (13)°	0.33 × 0.32 × 0.10 mm
V = 1100.1 (15) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3795 independent reflections
Radiation source: fine-focus sealed tube	2703 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 83.66 pixels mm^-1	θ_max = 25.0°, θ_min = 1.8°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
T_min = 0.868, T_max = 0.957	l = −14→14
9761 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0707P)² + 0.0622P] where P = (F_o² + 2F_c²)/3
3795 reflections	(Δ/σ)_max < 0.001
240 parameters	Δρ_max = 0.40 e Å⁻³
2 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₀H₂₃N₂S₄	γ = 106.082 (13)°
M_r = 419.64	V = 1100.1 (15) Å³
Triclinic, P1	Z = 2
a = 8.911 (7) Å	Mo Kα radiation
b = 11.568 (9) Å	µ = 0.44 mm⁻¹
c = 12.595 (10) Å	T = 298 K
α = 113.744 (11)°	0.33 × 0.32 × 0.10 mm
β = 97.157 (14)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3795 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2703 reflections with I > 2σ(I)
T_min = 0.868, T_max = 0.957	R_int = 0.027
9761 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	2 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.05	Δρ_max = 0.40 e Å⁻³
3795 reflections	Δρ_min = −0.31 e Å⁻³
240 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.52426 (10)	0.45806 (8)	0.12882 (7)	0.0705 (2)
S2	0.32106 (8)	0.27904 (7)	0.21979 (6)	0.0590 (2)
S3	0.15741 (8)	0.26777 (7)	0.08758 (6)	0.0627 (2)
S4	0.30485 (10)	0.06161 (7)	−0.04300 (7)	0.0692 (2)
N1	0.6376 (2)	0.38033 (19)	0.28434 (17)	0.0508 (5)
N2	0.0750 (3)	0.12026 (19)	−0.14498 (18)	0.0571 (5)
C1	0.5841 (3)	0.1797 (3)	0.3172 (2)	0.0641 (7)
H1	0.5790	0.1278	0.2371	0.077*
C2	0.5634 (4)	0.1214 (3)	0.3931 (3)	0.0834 (9)
H2	0.5422	0.0291	0.3638	0.100*
C3	0.5737 (4)	0.1983 (4)	0.5114 (3)	0.0900 (10)
H3	0.5618	0.1584	0.5623	0.108*
C4	0.6011 (4)	0.3317 (3)	0.5546 (3)	0.0787 (9)
H4	0.6067	0.3830	0.6349	0.094*
C5	0.6208 (3)	0.3923 (3)	0.4802 (2)	0.0595 (7)
H5	0.6394	0.4843	0.5103	0.071*
C6	0.6129 (3)	0.3169 (2)	0.3622 (2)	0.0493 (6)
C7	0.8070 (3)	0.4506 (3)	0.2889 (3)	0.0654 (7)
H7	0.8042	0.4574	0.2137	0.079*
C8	0.9107 (4)	0.3684 (4)	0.2937 (4)	0.0977 (11)
H8A	0.9157	0.3593	0.3664	0.146*
H8B	1.0180	0.4133	0.2924	0.146*
H8C	0.8641	0.2803	0.2254	0.146*
C9	0.8742 (4)	0.5933 (3)	0.3909 (3)	0.0962 (11)
H9A	0.8018	0.6394	0.3844	0.144*
H9B	0.9785	0.6407	0.3866	0.144*
H9C	0.8850	0.5903	0.4665	0.144*
C10	0.5127 (3)	0.3802 (2)	0.2131 (2)	0.0512 (6)
C11	0.1762 (3)	0.1387 (2)	−0.0473 (2)	0.0517 (6)
C12	0.0780 (4)	0.0257 (3)	−0.2668 (2)	0.0780 (9)
C13	−0.1002 (6)	−0.0424 (8)	−0.3523 (5)	0.090 (3)*	0.71 (2)
H13A	−0.1732	−0.0816	−0.3157	0.135*	0.71 (2)
H13B	−0.1036	−0.1118	−0.4283	0.135*	0.71 (2)
H13C	−0.1320	0.0249	−0.3648	0.135*	0.71 (2)
C13'	−0.068 (2)	−0.091 (2)	−0.3412 (15)	0.125 (7)*	0.29 (2)
H13D	−0.0882	−0.1507	−0.3047	0.188*	0.29 (2)
H13E	−0.0541	−0.1385	−0.4196	0.188*	0.29 (2)
H13F	−0.1580	−0.0623	−0.3485	0.188*	0.29 (2)
C14	0.1866 (5)	0.1022 (4)	−0.3166 (3)	0.1182 (14)
H14A	0.1381	0.1587	−0.3350	0.177*
H14B	0.2018	0.0396	−0.3886	0.177*
H14C	0.2897	0.1576	−0.2581	0.177*
C15	−0.0335 (3)	0.1942 (2)	−0.1358 (2)	0.0537 (6)
C16	−0.1814 (4)	0.1471 (3)	−0.1159 (3)	0.0749 (8)
H16	−0.2119	0.0675	−0.1087	0.090*
C17	−0.2840 (4)	0.2181 (4)	−0.1068 (3)	0.0896 (10)
H17	−0.3824	0.1881	−0.0905	0.107*
C18	−0.2423 (5)	0.3319 (4)	−0.1215 (3)	0.0877 (10)
H18	−0.3140	0.3775	−0.1184	0.105*
C19	−0.0951 (4)	0.3796 (3)	−0.1410 (3)	0.0795 (9)
H19	−0.0663	0.4582	−0.1497	0.095*
C20	0.0100 (4)	0.3113 (3)	−0.1476 (2)	0.0645 (7)
H20	0.1105	0.3441	−0.1600	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0809 (6)	0.0823 (5)	0.0684 (5)	0.0333 (4)	0.0190 (4)	0.0511 (4)
S2	0.0563 (4)	0.0778 (5)	0.0483 (4)	0.0257 (3)	0.0152 (3)	0.0325 (3)
S3	0.0616 (5)	0.0791 (5)	0.0463 (4)	0.0379 (4)	0.0123 (3)	0.0201 (3)
S4	0.0863 (6)	0.0735 (5)	0.0666 (5)	0.0480 (4)	0.0291 (4)	0.0349 (4)
N1	0.0518 (13)	0.0603 (12)	0.0472 (11)	0.0227 (10)	0.0116 (10)	0.0298 (10)
N2	0.0773 (16)	0.0566 (12)	0.0438 (11)	0.0301 (11)	0.0163 (11)	0.0250 (10)
C1	0.080 (2)	0.0596 (15)	0.0594 (16)	0.0348 (14)	0.0210 (15)	0.0271 (13)
C2	0.106 (3)	0.0675 (18)	0.098 (3)	0.0397 (18)	0.028 (2)	0.0519 (19)
C3	0.109 (3)	0.107 (3)	0.088 (2)	0.043 (2)	0.033 (2)	0.071 (2)
C4	0.097 (2)	0.096 (2)	0.0562 (17)	0.0405 (19)	0.0260 (16)	0.0420 (17)
C5	0.0689 (19)	0.0657 (16)	0.0501 (15)	0.0321 (14)	0.0181 (13)	0.0265 (13)
C6	0.0497 (15)	0.0579 (14)	0.0490 (14)	0.0254 (11)	0.0139 (11)	0.0287 (12)
C7	0.0566 (18)	0.0805 (18)	0.0600 (16)	0.0152 (14)	0.0116 (13)	0.0403 (15)
C8	0.061 (2)	0.128 (3)	0.122 (3)	0.041 (2)	0.033 (2)	0.066 (3)
C9	0.090 (3)	0.086 (2)	0.089 (2)	0.0049 (19)	0.009 (2)	0.040 (2)
C10	0.0604 (16)	0.0512 (13)	0.0418 (13)	0.0240 (12)	0.0143 (12)	0.0186 (11)
C11	0.0602 (16)	0.0511 (13)	0.0480 (14)	0.0210 (12)	0.0178 (12)	0.0251 (11)
C12	0.114 (3)	0.0759 (19)	0.0459 (16)	0.0452 (19)	0.0189 (17)	0.0229 (14)
C14	0.152 (4)	0.141 (3)	0.089 (3)	0.069 (3)	0.075 (3)	0.056 (3)
C15	0.0612 (17)	0.0555 (14)	0.0453 (14)	0.0202 (13)	0.0112 (12)	0.0254 (12)
C16	0.071 (2)	0.0747 (19)	0.075 (2)	0.0120 (16)	0.0120 (16)	0.0423 (16)
C17	0.058 (2)	0.114 (3)	0.093 (2)	0.0278 (19)	0.0205 (18)	0.045 (2)
C18	0.092 (3)	0.112 (3)	0.080 (2)	0.060 (2)	0.0216 (19)	0.048 (2)
C19	0.102 (3)	0.085 (2)	0.086 (2)	0.0537 (19)	0.0393 (19)	0.0544 (18)
C20	0.0693 (19)	0.0676 (17)	0.0675 (18)	0.0273 (15)	0.0232 (15)	0.0379 (15)

Geometric parameters (Å, º) top

S1—C10	1.642 (3)	C8—H8C	0.9600
S2—C10	1.817 (3)	C9—H9A	0.9600
S2—S3	2.0078 (15)	C9—H9B	0.9600
S3—C11	1.819 (3)	C9—H9C	0.9600
S4—C11	1.644 (3)	C12—C13'	1.449 (9)
N1—C10	1.339 (3)	C12—C14	1.496 (5)
N1—C6	1.446 (3)	C12—C13	1.581 (6)
N1—C7	1.484 (3)	C13—H13A	0.9600
N2—C11	1.333 (3)	C13—H13B	0.9600
N2—C15	1.445 (3)	C13—H13C	0.9600
N2—C12	1.492 (3)	C13'—H13D	0.9600
C1—C2	1.378 (4)	C13'—H13E	0.9600
C1—C6	1.386 (3)	C13'—H13F	0.9600
C1—H1	0.9300	C14—H14A	0.9600
C2—C3	1.369 (5)	C14—H14B	0.9600
C2—H2	0.9300	C14—H14C	0.9600
C3—C4	1.349 (4)	C15—C16	1.375 (4)
C3—H3	0.9300	C15—C20	1.375 (4)
C4—C5	1.379 (4)	C16—C17	1.375 (4)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.368 (3)	C17—C18	1.359 (5)
C5—H5	0.9300	C17—H17	0.9300
C7—C8	1.510 (4)	C18—C19	1.368 (5)
C7—C9	1.512 (4)	C18—H18	0.9300
C7—H7	0.9800	C19—C20	1.373 (4)
C8—H8A	0.9600	C19—H19	0.9300
C8—H8B	0.9600	C20—H20	0.9300

C10—S2—S3	103.48 (10)	N1—C10—S2	110.83 (18)
C11—S3—S2	102.95 (10)	S1—C10—S2	122.82 (15)
C10—N1—C6	121.5 (2)	N2—C11—S4	127.04 (19)
C10—N1—C7	120.6 (2)	N2—C11—S3	110.37 (18)
C6—N1—C7	117.85 (19)	S4—C11—S3	122.58 (15)
C11—N2—C15	121.3 (2)	C13'—C12—N2	117.7 (8)
C11—N2—C12	119.6 (2)	C13'—C12—C14	123.1 (9)
C15—N2—C12	119.0 (2)	N2—C12—C14	110.0 (3)
C2—C1—C6	118.9 (3)	C13'—C12—C13	28.4 (12)
C2—C1—H1	120.6	N2—C12—C13	108.1 (3)
C6—C1—H1	120.6	C14—C12—C13	108.9 (4)
C3—C2—C1	120.4 (3)	C12—C13—H13A	109.5
C3—C2—H2	119.8	C12—C13—H13B	109.5
C1—C2—H2	119.8	C12—C13—H13C	109.5
C4—C3—C2	120.4 (3)	C12—C13'—H13D	109.5
C4—C3—H3	119.8	C12—C13'—H13E	109.5
C2—C3—H3	119.8	H13D—C13'—H13E	109.5
C3—C4—C5	120.3 (3)	C12—C13'—H13F	109.5
C3—C4—H4	119.9	H13D—C13'—H13F	109.5
C5—C4—H4	119.9	H13E—C13'—H13F	109.5
C6—C5—C4	119.9 (3)	C12—C14—H14A	109.5
C6—C5—H5	120.1	C12—C14—H14B	109.5
C4—C5—H5	120.1	H14A—C14—H14B	109.5
C5—C6—C1	120.1 (2)	C12—C14—H14C	109.5
C5—C6—N1	120.2 (2)	H14A—C14—H14C	109.5
C1—C6—N1	119.6 (2)	H14B—C14—H14C	109.5
N1—C7—C8	110.9 (2)	C16—C15—C20	119.8 (3)
N1—C7—C9	110.6 (2)	C16—C15—N2	119.9 (2)
C8—C7—C9	113.3 (3)	C20—C15—N2	120.3 (2)
N1—C7—H7	107.2	C17—C16—C15	119.7 (3)
C8—C7—H7	107.2	C17—C16—H16	120.2
C9—C7—H7	107.2	C15—C16—H16	120.2
C7—C8—H8A	109.5	C18—C17—C16	120.3 (3)
C7—C8—H8B	109.5	C18—C17—H17	119.8
H8A—C8—H8B	109.5	C16—C17—H17	119.8
C7—C8—H8C	109.5	C17—C18—C19	120.2 (3)
H8A—C8—H8C	109.5	C17—C18—H18	119.9
H8B—C8—H8C	109.5	C19—C18—H18	119.9
C7—C9—H9A	109.5	C18—C19—C20	120.0 (3)
C7—C9—H9B	109.5	C18—C19—H19	120.0
H9A—C9—H9B	109.5	C20—C19—H19	120.0
C7—C9—H9C	109.5	C19—C20—C15	119.9 (3)
H9A—C9—H9C	109.5	C19—C20—H20	120.1
H9B—C9—H9C	109.5	C15—C20—H20	120.1
N1—C10—S1	126.3 (2)

C10—S2—S3—C11	78.60 (13)	C12—N2—C11—S4	−3.2 (4)
C6—C1—C2—C3	−1.1 (5)	C15—N2—C11—S3	−1.7 (3)
C1—C2—C3—C4	1.4 (5)	C12—N2—C11—S3	175.73 (19)
C2—C3—C4—C5	−0.7 (5)	S2—S3—C11—N2	−179.16 (16)
C3—C4—C5—C6	−0.1 (5)	S2—S3—C11—S4	−0.20 (17)
C4—C5—C6—C1	0.4 (4)	C11—N2—C12—C13'	118.0 (16)
C4—C5—C6—N1	−178.4 (2)	C15—N2—C12—C13'	−64.5 (16)
C2—C1—C6—C5	0.2 (4)	C11—N2—C12—C14	−94.0 (3)
C2—C1—C6—N1	179.0 (3)	C15—N2—C12—C14	83.5 (3)
C10—N1—C6—C5	−95.6 (3)	C11—N2—C12—C13	147.1 (4)
C7—N1—C6—C5	82.2 (3)	C15—N2—C12—C13	−35.4 (5)
C10—N1—C6—C1	85.6 (3)	C11—N2—C15—C16	−85.1 (3)
C7—N1—C6—C1	−96.6 (3)	C12—N2—C15—C16	97.4 (3)
C10—N1—C7—C8	−139.6 (3)	C11—N2—C15—C20	95.4 (3)
C6—N1—C7—C8	42.6 (3)	C12—N2—C15—C20	−82.1 (3)
C10—N1—C7—C9	93.8 (3)	C20—C15—C16—C17	−0.7 (4)
C6—N1—C7—C9	−84.0 (3)	N2—C15—C16—C17	179.8 (3)
C6—N1—C10—S1	174.94 (17)	C15—C16—C17—C18	2.3 (5)
C7—N1—C10—S1	−2.8 (3)	C16—C17—C18—C19	−2.5 (5)
C6—N1—C10—S2	−5.4 (3)	C17—C18—C19—C20	1.0 (5)
C7—N1—C10—S2	176.84 (18)	C18—C19—C20—C15	0.6 (5)
S3—S2—C10—N1	−170.73 (15)	C16—C15—C20—C19	−0.8 (4)
S3—S2—C10—S1	8.93 (16)	N2—C15—C20—C19	178.8 (2)
C15—N2—C11—S4	179.36 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···S1	0.98	2.59	3.068 (4)	110

Experimental details

Crystal data
Chemical formula	C₂₀H₂₃N₂S₄
M_r	419.64
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.911 (7), 11.568 (9), 12.595 (10)
α, β, γ (°)	113.744 (11), 97.157 (14), 106.082 (13)
V (Å³)	1100.1 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.33 × 0.32 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.868, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	9761, 3795, 2703
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.125, 1.05
No. of reflections	3795
No. of parameters	240
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.31

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

S1—C10	1.642 (3)	N1—C6	1.446 (3)
S2—C10	1.817 (3)	N1—C7	1.484 (3)
S2—S3	2.0078 (15)	N2—C11	1.333 (3)
S3—C11	1.819 (3)	N2—C15	1.445 (3)
S4—C11	1.644 (3)	N2—C12	1.492 (3)
N1—C10	1.339 (3)

N1—C10—S1	126.3 (2)	N2—C11—S4	127.04 (19)
N1—C10—S2	110.83 (18)	N2—C11—S3	110.37 (18)
S1—C10—S2	122.82 (15)	S4—C11—S3	122.58 (15)

C6—N1—C10—S1	174.94 (17)	C15—N2—C11—S4	179.36 (18)
C6—N1—C10—S2	−5.4 (3)	C15—N2—C11—S3	−1.7 (3)

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Bis(N-isopropyl-N-phenyl­thio­carbamo­yl) disulfide

Supporting information

Key indicators

checkCIF/PLATON results

Bis(N-isopropyl-N-phenylthiocarbamoyl) disulfide