Bis(1,2,3,4-tetra­hydro­quinoline-1-thio­carbon­yl) disulfide

Srinivasan, N.; Thirumaran, S.; Selvanayagam, S.

doi:10.1107/S1600536812047320

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3446

doi:10.1107/S1600536812047320

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Bis(1,2,3,4-tetrahydroquinoline-1-thiocarbonyl) disulfide

N. Srinivasan,^a S. Thirumaran ^a and S. Selvanayagam ^b ^*

^aDepartment of Chemistry, Annamalai University, Annamalainagar 608 002, India, and ^bDepartment of Physics, Kalasalingam University, Krishnankoil 626 126, India
^*Correspondence e-mail: s_selvanayagam@rediffmail.com

(Received 21 October 2012; accepted 17 November 2012; online 24 November 2012)

In the title compound, C₂₀H₂₀N₂S₄, the N-containing six-membered rings of the two tetrahydroquinoline moieties adopt half-chair conformations. Intramolecular C—H⋯S hydrogen bonding stabilizes the molecular structure. In the crystal, molecules associate via weak C—H⋯π interactions.

Related literature

For general background to the title compound, see: Von Deuten et al. (1980 ); Kumar et al. (1990 ); Fun et al. (2001 ). For preparation of the title compound, see: Garg et al. (1993 ). For related structures, see: Ivanov et al. (2003 ); Jian et al. (1999 ); Fun et al. (2001). For ring-puckering parameters, see: Nardelli (1983 ).

Experimental

Crystal data

C₂₀H₂₀N₂S₄
M_r = 416.62
Monoclinic, P 2₁ /c
a = 8.1019 (4) Å
b = 20.3208 (11) Å
c = 12.3647 (6) Å
β = 104.371 (2)°
V = 1971.99 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 292 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.867, T_max = 0.909
44844 measured reflections
4941 independent reflections
4036 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.104
S = 1.03
4941 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4–C9 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12B⋯S4	0.97	2.53	3.028 (2)	112
C18—H18⋯Cg1ⁱ		2.74	3.604 (2)	154
Symmetry code: (i) -x, -y, -z+2.

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2; data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97 and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812047320/zq2186sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812047320/zq2186Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812047320/zq2186Isup3.cml

checkCIF report

Comment top

The bis(dialkylthiocarbomyl)disulfide compounds are the immediate oxidation products of dithiocarbamic acids and are known to be formed as one of the products during redox complexation reactions of dithiocarbamates with metal ions like Te^IV, Se^IV, La^III etc··· (Von Deuten et al., 1980; Kumar et al., 1990; Fun et al., 2001). In the course of our investigations on the sodium salt of 1,2,3,4-tetrahydroquinolinecarbodithioate, we noticed the formation of bis(1,2,3,4-tetrahydroquinolinethiocarbomyl)disulphide. To study the structural features of this compound, we have undertaken its crystal structure determination and the results are presented here.

The X-ray study confirmed the molecular structure and atomic connectivity as illustrated in Fig. 1. The S—S bond distance of 1.9958 (6) Å is close to the related literature value (Ivanov et al., 2003; Jian et al., 1999; Fun et al., 2001). Two sets of significantly different C—S distances are observed and these distances are clearly corresponding to single and double bonded C—S distances. The two C=S bonds are trans to each other. The N-containing six membered rings of the two tetrahydroquinoline moieties have a half-chair conformation with the lowest asymmetry parameters of ΔC₂(N1-C9) = 0.038 (1)° and ΔC₂(C12-N2) = 0.080 (1)° (Nardelli, 1983).

The molecular structure is influenced by an intramolecular C—H···S hydrogen bond (Fig. 2 and Table 1). In addition, intermolecular C—H···π interactions are observed with H18···Cg1ⁱ = 2.74 Å, C18—H18···Cg1ⁱ = 154°, and C18···Cg1ⁱ = 3.604 (2) Å [Cg1 is the centroid of the phenyl ring (C4-C9) and the symmetry operation i corresponds to -x, -y, 2-z] (Fig. 2).

Related literature top

For general background to the title compound, see: Von Deuten et al. (1980); Kumar et al. (1990); Fun et al. (2001). For preparation of the title compound, see: Garg et al. (1993). For related structures, see: Ivanov et al. (2003); Jian et al. (1999); Fun et al. (2001). For ring-puckering parameters, see: Nardelli (1983).

Experimental top

Recrystallization of sodium 1,2,3,4-tetrahydroquinolinecarbodithioate (Garg et al., 1993) from a chloroform solution yielded the title compound as pale yellow crystals.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level
	Fig. 2. Molecular packing of the title compound, viewed along the a axis (H-bonds are shown as dashed lines). For the sake of clarity, H atoms, not involved in hydrogen bonds, have been omitted

Bis(1,2,3,4-tetrahydroquinoline-1-thiocarbonyl) disulfide top

Crystal data top

C₂₀H₂₀N₂S₄	F(000) = 872
M_r = 416.62	D_x = 1.403 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8987 reflections
a = 8.1019 (4) Å	θ = 2.5–28.3°
b = 20.3208 (11) Å	µ = 0.49 mm⁻¹
c = 12.3647 (6) Å	T = 292 K
β = 104.371 (2)°	Block, yellow
V = 1971.99 (17) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	4941 independent reflections
Radiation source: fine-focus sealed tube	4036 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω and ϕ scans	θ_max = 28.4°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
T_min = 0.867, T_max = 0.909	k = −25→27
44844 measured reflections	l = −16→14

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0495P)² + 0.8147P] where P = (F_o² + 2F_c²)/3
4941 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₀H₂₀N₂S₄	V = 1971.99 (17) Å³
M_r = 416.62	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1019 (4) Å	µ = 0.49 mm⁻¹
b = 20.3208 (11) Å	T = 292 K
c = 12.3647 (6) Å	0.30 × 0.25 × 0.20 mm
β = 104.371 (2)°

Data collection top

Bruker APEXII area-detector diffractometer	4941 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4036 reflections with I > 2σ(I)
T_min = 0.867, T_max = 0.909	R_int = 0.031
44844 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.03	Δρ_max = 0.53 e Å⁻³
4941 reflections	Δρ_min = −0.26 e Å⁻³
235 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.7070 (2)	0.12620 (11)	0.98073 (17)	0.0529 (5)
H1A	0.7149	0.1479	0.9124	0.064*
H1B	0.7356	0.0802	0.9749	0.064*
C2	0.8343 (3)	0.15668 (13)	1.0777 (2)	0.0640 (6)
H2A	0.8437	0.2034	1.0642	0.077*
H2B	0.9453	0.1369	1.0842	0.077*
C3	0.7814 (3)	0.14684 (12)	1.18582 (18)	0.0585 (5)
H3A	0.7667	0.1004	1.1988	0.070*
H3B	0.8674	0.1644	1.2482	0.070*
C4	0.6170 (2)	0.18262 (8)	1.17373 (15)	0.0425 (4)
C5	0.5862 (3)	0.22676 (9)	1.25173 (16)	0.0510 (5)
H5	0.6677	0.2324	1.3188	0.061*
C6	0.4374 (3)	0.26245 (9)	1.23197 (18)	0.0555 (5)
H6	0.4168	0.2904	1.2867	0.067*
C7	0.3195 (3)	0.25670 (9)	1.13155 (18)	0.0520 (5)
H7	0.2192	0.2810	1.1182	0.062*
C8	0.3489 (2)	0.21484 (8)	1.04965 (16)	0.0437 (4)
H8	0.2719	0.2127	0.9800	0.052*
C9	0.4944 (2)	0.17619 (8)	1.07291 (13)	0.0367 (3)
C10	0.4118 (2)	0.09180 (8)	0.92624 (13)	0.0383 (3)
C11	−0.0542 (2)	0.09836 (8)	0.76717 (14)	0.0380 (3)
C12	−0.2722 (3)	0.12260 (12)	0.59730 (19)	0.0682 (6)
H12A	−0.3939	0.1145	0.5813	0.082*
H12B	−0.2508	0.1677	0.6225	0.082*
C13	−0.2106 (5)	0.11167 (18)	0.4968 (2)	0.1054 (11)
H13A	−0.0911	0.1237	0.5127	0.126*
H13B	−0.2724	0.1405	0.4380	0.126*
C14	−0.2300 (5)	0.04240 (16)	0.4557 (2)	0.0900 (9)
H14A	−0.1377	0.0325	0.4211	0.108*
H14B	−0.3359	0.0389	0.3984	0.108*
C15	−0.2305 (3)	−0.00897 (12)	0.54424 (17)	0.0596 (5)
C16	−0.2603 (4)	−0.07527 (14)	0.5177 (2)	0.0752 (7)
H16	−0.2693	−0.0890	0.4448	0.090*
C17	−0.2768 (3)	−0.12063 (13)	0.5960 (2)	0.0734 (7)
H17	−0.2927	−0.1648	0.5764	0.088*
C18	−0.2701 (3)	−0.10132 (11)	0.70323 (19)	0.0586 (5)
H18	−0.2844	−0.1320	0.7559	0.070*
C19	−0.2420 (2)	−0.03635 (9)	0.73215 (16)	0.0455 (4)
H19	−0.2413	−0.0227	0.8040	0.055*
C20	−0.2147 (2)	0.00878 (9)	0.65492 (14)	0.0422 (4)
N1	0.52917 (18)	0.13106 (7)	0.99185 (12)	0.0385 (3)
N2	−0.18060 (19)	0.07682 (7)	0.68409 (13)	0.0444 (3)
S1	0.22177 (6)	0.08105 (2)	0.97636 (3)	0.04264 (12)
S2	0.06107 (6)	0.03269 (2)	0.85363 (4)	0.04694 (13)
S3	0.44036 (8)	0.05131 (3)	0.81800 (4)	0.06045 (16)
S4	0.00011 (7)	0.17623 (2)	0.79093 (5)	0.05336 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0466 (10)	0.0613 (12)	0.0562 (11)	0.0073 (9)	0.0229 (9)	−0.0019 (9)
C2	0.0405 (10)	0.0747 (15)	0.0793 (15)	−0.0006 (10)	0.0196 (10)	−0.0060 (12)
C3	0.0498 (11)	0.0644 (13)	0.0549 (11)	0.0057 (9)	0.0009 (9)	−0.0048 (10)
C4	0.0478 (9)	0.0367 (8)	0.0431 (9)	−0.0052 (7)	0.0116 (7)	0.0007 (7)
C5	0.0648 (12)	0.0434 (10)	0.0436 (10)	−0.0123 (9)	0.0111 (9)	−0.0067 (8)
C6	0.0783 (14)	0.0384 (9)	0.0570 (12)	−0.0083 (9)	0.0304 (11)	−0.0139 (8)
C7	0.0597 (11)	0.0366 (9)	0.0651 (12)	0.0079 (8)	0.0258 (10)	−0.0026 (8)
C8	0.0490 (10)	0.0371 (9)	0.0460 (9)	0.0039 (7)	0.0135 (8)	0.0008 (7)
C9	0.0442 (9)	0.0309 (7)	0.0377 (8)	−0.0020 (6)	0.0155 (7)	0.0003 (6)
C10	0.0448 (9)	0.0364 (8)	0.0343 (8)	0.0076 (7)	0.0111 (7)	0.0011 (6)
C11	0.0365 (8)	0.0398 (8)	0.0393 (8)	0.0039 (6)	0.0125 (7)	0.0081 (7)
C12	0.0667 (14)	0.0599 (13)	0.0633 (13)	0.0076 (11)	−0.0118 (11)	0.0170 (11)
C13	0.150 (3)	0.102 (2)	0.0621 (16)	0.012 (2)	0.0215 (18)	0.0363 (16)
C14	0.119 (2)	0.112 (2)	0.0363 (11)	−0.0270 (19)	0.0133 (13)	0.0061 (13)
C15	0.0585 (12)	0.0782 (15)	0.0382 (10)	−0.0094 (11)	0.0045 (8)	−0.0036 (9)
C16	0.0833 (17)	0.0879 (18)	0.0507 (13)	−0.0143 (14)	0.0095 (12)	−0.0266 (12)
C17	0.0784 (16)	0.0589 (13)	0.0758 (16)	−0.0134 (12)	0.0056 (13)	−0.0232 (12)
C18	0.0581 (12)	0.0505 (11)	0.0625 (12)	−0.0118 (9)	0.0060 (10)	−0.0009 (9)
C19	0.0436 (9)	0.0501 (10)	0.0423 (9)	−0.0058 (8)	0.0099 (7)	−0.0012 (8)
C20	0.0357 (8)	0.0508 (10)	0.0376 (8)	−0.0013 (7)	0.0046 (7)	−0.0003 (7)
N1	0.0401 (7)	0.0385 (7)	0.0389 (7)	0.0036 (6)	0.0134 (6)	−0.0019 (6)
N2	0.0421 (8)	0.0454 (8)	0.0421 (8)	0.0009 (6)	0.0035 (6)	0.0090 (6)
S1	0.0451 (2)	0.0481 (2)	0.0342 (2)	−0.00396 (18)	0.00894 (17)	0.00092 (17)
S2	0.0513 (3)	0.0346 (2)	0.0467 (2)	−0.00014 (18)	−0.00342 (19)	0.00393 (17)
S3	0.0659 (3)	0.0696 (3)	0.0481 (3)	0.0074 (3)	0.0184 (2)	−0.0206 (2)
S4	0.0521 (3)	0.0362 (2)	0.0681 (3)	0.00046 (19)	0.0078 (2)	0.0086 (2)

Geometric parameters (Å, º) top

C1—N1	1.484 (2)	C11—S4	1.6491 (18)
C1—C2	1.508 (3)	C11—S2	1.8167 (16)
C1—H1A	0.9700	C12—C13	1.467 (4)
C1—H1B	0.9700	C12—N2	1.474 (2)
C2—C3	1.515 (3)	C12—H12A	0.9700
C2—H2A	0.9700	C12—H12B	0.9700
C2—H2B	0.9700	C13—C14	1.492 (5)
C3—C4	1.492 (3)	C13—H13A	0.9700
C3—H3A	0.9700	C13—H13B	0.9700
C3—H3B	0.9700	C14—C15	1.514 (3)
C4—C5	1.384 (3)	C14—H14A	0.9700
C4—C9	1.394 (2)	C14—H14B	0.9700
C5—C6	1.376 (3)	C15—C20	1.390 (3)
C5—H5	0.9300	C15—C16	1.393 (4)
C6—C7	1.371 (3)	C16—C17	1.367 (4)
C6—H6	0.9300	C16—H16	0.9300
C7—C8	1.388 (3)	C17—C18	1.371 (3)
C7—H7	0.9300	C17—H17	0.9300
C8—C9	1.386 (2)	C18—C19	1.372 (3)
C8—H8	0.9300	C18—H18	0.9300
C9—N1	1.437 (2)	C19—C20	1.381 (3)
C10—N1	1.347 (2)	C19—H19	0.9300
C10—S3	1.6355 (17)	C20—N2	1.438 (2)
C10—S1	1.8102 (18)	S1—S2	1.9958 (6)
C11—N2	1.332 (2)

N1—C1—C2	112.79 (16)	C13—C12—H12A	110.2
N1—C1—H1A	109.0	N2—C12—H12A	110.2
C2—C1—H1A	109.0	C13—C12—H12B	110.2
N1—C1—H1B	109.0	N2—C12—H12B	110.2
C2—C1—H1B	109.0	H12A—C12—H12B	108.5
H1A—C1—H1B	107.8	C12—C13—C14	113.7 (3)
C1—C2—C3	111.09 (18)	C12—C13—H13A	108.8
C1—C2—H2A	109.4	C14—C13—H13A	108.8
C3—C2—H2A	109.4	C12—C13—H13B	108.8
C1—C2—H2B	109.4	C14—C13—H13B	108.8
C3—C2—H2B	109.4	H13A—C13—H13B	107.7
H2A—C2—H2B	108.0	C13—C14—C15	115.0 (2)
C4—C3—C2	106.76 (18)	C13—C14—H14A	108.5
C4—C3—H3A	110.4	C15—C14—H14A	108.5
C2—C3—H3A	110.4	C13—C14—H14B	108.5
C4—C3—H3B	110.4	C15—C14—H14B	108.5
C2—C3—H3B	110.4	H14A—C14—H14B	107.5
H3A—C3—H3B	108.6	C20—C15—C16	116.8 (2)
C5—C4—C9	118.17 (17)	C20—C15—C14	121.1 (2)
C5—C4—C3	123.85 (18)	C16—C15—C14	121.9 (2)
C9—C4—C3	117.65 (16)	C17—C16—C15	121.8 (2)
C6—C5—C4	121.30 (18)	C17—C16—H16	119.1
C6—C5—H5	119.3	C15—C16—H16	119.1
C4—C5—H5	119.3	C16—C17—C18	120.3 (2)
C7—C6—C5	119.92 (18)	C16—C17—H17	119.9
C7—C6—H6	120.0	C18—C17—H17	119.9
C5—C6—H6	120.0	C17—C18—C19	119.5 (2)
C6—C7—C8	120.40 (19)	C17—C18—H18	120.3
C6—C7—H7	119.8	C19—C18—H18	120.3
C8—C7—H7	119.8	C18—C19—C20	120.24 (19)
C9—C8—C7	119.15 (18)	C18—C19—H19	119.9
C9—C8—H8	120.4	C20—C19—H19	119.9
C7—C8—H8	120.4	C19—C20—C15	121.13 (19)
C8—C9—C4	120.86 (16)	C19—C20—N2	121.26 (16)
C8—C9—N1	121.37 (15)	C15—C20—N2	117.47 (17)
C4—C9—N1	117.66 (15)	C10—N1—C9	124.53 (14)
N1—C10—S3	124.66 (13)	C10—N1—C1	117.45 (14)
N1—C10—S1	113.48 (12)	C9—N1—C1	118.02 (14)
S3—C10—S1	121.63 (11)	C11—N2—C20	124.92 (14)
N2—C11—S4	124.95 (13)	C11—N2—C12	120.41 (16)
N2—C11—S2	113.40 (13)	C20—N2—C12	113.17 (15)
S4—C11—S2	121.64 (10)	C10—S1—S2	104.42 (6)
C13—C12—N2	107.8 (2)	C11—S2—S1	103.22 (6)

N1—C1—C2—C3	34.8 (3)	C16—C15—C20—N2	178.84 (19)
C1—C2—C3—C4	−63.3 (2)	C14—C15—C20—N2	−6.2 (3)
C2—C3—C4—C5	−129.7 (2)	S3—C10—N1—C9	167.43 (13)
C2—C3—C4—C9	43.5 (2)	S1—C10—N1—C9	−18.1 (2)
C9—C4—C5—C6	1.4 (3)	S3—C10—N1—C1	−13.8 (2)
C3—C4—C5—C6	174.54 (19)	S1—C10—N1—C1	160.63 (13)
C4—C5—C6—C7	−2.8 (3)	C8—C9—N1—C10	−42.2 (2)
C5—C6—C7—C8	0.3 (3)	C4—C9—N1—C10	141.44 (17)
C6—C7—C8—C9	3.6 (3)	C8—C9—N1—C1	139.04 (17)
C7—C8—C9—C4	−5.0 (3)	C4—C9—N1—C1	−37.3 (2)
C7—C8—C9—N1	178.73 (16)	C2—C1—N1—C10	−163.64 (18)
C5—C4—C9—C8	2.6 (3)	C2—C1—N1—C9	15.2 (2)
C3—C4—C9—C8	−171.03 (17)	S4—C11—N2—C20	171.86 (14)
C5—C4—C9—N1	178.96 (15)	S2—C11—N2—C20	−6.8 (2)
C3—C4—C9—N1	5.4 (2)	S4—C11—N2—C12	6.8 (3)
N2—C12—C13—C14	56.7 (4)	S2—C11—N2—C12	−171.84 (16)
C12—C13—C14—C15	−26.7 (4)	C19—C20—N2—C11	56.4 (3)
C13—C14—C15—C20	0.4 (4)	C15—C20—N2—C11	−127.8 (2)
C13—C14—C15—C16	175.1 (3)	C19—C20—N2—C12	−137.60 (19)
C20—C15—C16—C17	1.3 (4)	C15—C20—N2—C12	38.2 (2)
C14—C15—C16—C17	−173.7 (3)	C13—C12—N2—C11	103.4 (3)
C15—C16—C17—C18	2.3 (4)	C13—C12—N2—C20	−63.3 (3)
C16—C17—C18—C19	−1.8 (4)	N1—C10—S1—S2	172.06 (11)
C17—C18—C19—C20	−2.3 (3)	S3—C10—S1—S2	−13.32 (12)
C18—C19—C20—C15	6.0 (3)	N2—C11—S2—S1	−174.41 (12)
C18—C19—C20—N2	−178.37 (17)	S4—C11—S2—S1	6.88 (12)
C16—C15—C20—C19	−5.4 (3)	C10—S1—S2—C11	−90.59 (8)
C14—C15—C20—C19	169.6 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C4–C9 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···S4	0.97	2.53	3.028 (2)	112
C18—H18···Cg1ⁱ		2.74	3.604 (2)	154

Symmetry code: (i) −x, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀N₂S₄
M_r	416.62
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	292
a, b, c (Å)	8.1019 (4), 20.3208 (11), 12.3647 (6)
β (°)	104.371 (2)
V (Å³)	1971.99 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.49
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.867, 0.909
No. of measured, independent and observed [I > 2σ(I)] reflections	44844, 4941, 4036
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.104, 1.03
No. of reflections	4941
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.26

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C4–C9 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···S4	0.97	2.53	3.028 (2)	112
C18—H18···Cg1ⁱ	.	2.74	3.604 (2)	154

Symmetry code: (i) −x, −y, −z+2.

Acknowledgements

The authors thank the SAIF, Indian Institute of Technology, Chennai, for the data collection.

References

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