N-[(3-Phenyl­sulfanyl-1-phenyl­sulfonyl-1H-indol-2-yl)meth­yl]propionamide

Umadevi, M.; Dhayalan, V.; Mohanakrishnan, A.K.; Chakkaravarthi, G.; Manivannan, V.

doi:10.1107/S1600536809041518

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2916

https://doi.org/10.1107/S1600536809041518

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N-[(3-Phenylsulfanyl-1-phenylsulfonyl-1H-indol-2-yl)methyl]propionamide

M. Umadevi,^a V. Dhayalan,^b A. K. Mohanakrishnan,^b G. Chakkaravarthi ^c and V. Manivannan ^d ^*

^aDepartment of Chemistry, Pallavan College of Engineering, Kanchipuram 631 502, Tamilnadu, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, ^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and ^dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
^*Correspondence e-mail: manivan_1999@yahoo.com

(Received 9 September 2009; accepted 11 October 2009; online 31 October 2009)

In the title compound, C₂₄H₂₂N₂O₃S₂, the phenyl rings form dihedral angles of 75.2 (1) and 86.1 (1)° with the indole ring system. The molecular structure is stabilized by intramolecular C–H⋯O and N—H⋯O hydrogen bonds. The crystal structure exhibit intermolecular N—H⋯O and C—H⋯O hydrogen bonds, C—H⋯π and π–π [centroid–centroid distance = 3.748 (1) Å] interactions.

Related literature

For the biological activity of indole derivatives, see: Nieto et al. (2005 ); Olgen & Coban (2003 ). For related structures, see: Chakkaravarthi et al. (2007 , 2008 ).

Experimental

Crystal data

C₂₄H₂₂N₂O₃S₂
M_r = 450.56
Monoclinic, P 2₁ /c
a = 10.9216 (3) Å
b = 23.1856 (6) Å
c = 9.4298 (2) Å
β = 110.147 (1)°
V = 2241.74 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 295 K
0.26 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.934, T_max = 0.959
26619 measured reflections
5543 independent reflections
3962 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.117
S = 1.04
5543 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2	0.86	2.52	2.939 (2)	111
C13—H13⋯O1	0.93	2.37	2.921 (3)	118
C18—H18⋯O2ⁱ	0.93	2.52	3.317 (3)	144
N2—H2A⋯O3ⁱⁱ	0.86	2.15	2.899 (2)	145
C16—H16⋯O3ⁱⁱ	0.93	2.60	3.416 (3)	147
C10—H10⋯Cg2ⁱⁱⁱ	0.93	2.81	3.658 (2)	152
C5—H5⋯Cg4^iv	0.93	2.91	3.788 (4)	158
Symmetry codes: (i) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x+1, y, z; (iv) -x, -y, -z. Cg2 and Cg4 are the centroids of C1–C6 and C15–C20 rings, respectively.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809041518/gw2070sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809041518/gw2070Isup2.hkl

checkCIF report

Comment top

In continuation of our studies of indole derivatives, which are known to exhibit anti-oxidant (Olgen & Coban, 2003) and antibacterial (Nieto et al., 2005) activities, we report the crystal structure of the title compound (I). The geometric parameters in (I) (Fig. 1) agree with the reported values of similar structures (Chakkaravarthi et al., 2007, 2008).

The phenyl rings C1—C6 and C15—C20 form the dihedral angles of 75.2 (1)° and 86.1 (1)°, respectively, with the indole ring system. The mean planes of the two phenyl rings are inclined at an angle of 78.7 (1)° with respect to each other. A distorted tetrahedral geometry [N1- S1- O1 106.3 (1)° and N1—S1—O2 106.4 (1)°] is observed around S1 atom.

The molecular structure is stabilized by intramolecular C—H···O and N—H···O hydrogen bonds and the crystal structure exhibit intermolecular N—H···O and C—H···O hydrogen bonds, C—H···π (Table 1 and Fig. 2) and π···π [Cg1···Cg3 3.748 (1) Å; symmetry code: -x, -y, -z; Cg1 and Cg3 are the centroids of N1/C7/C8/C9/C14 and C9—C14 rings, respectively] interactions.

Related literature top

For the biological activity of indole derivatives, see: Nieto et al. (2005); Olgen & Coban (2003). For related structures, see: Chakkaravarthi et al. (2007, 2008). Cg2 and Cg4 are the centroids of C1–C6 and C15–C20 rings, respectively.

Experimental top

To a solution of 1-phenylsulfonyl-(3-(phenylthio)-2-bromomethylindole (0.5 g, 1.09 mmol) in dry 1,2-dimethoxyethane (20 ml), ZnBr₂ (0.5 g, 2.22 mmol) and propiononitrile (0.24 g, 4.35 mmol) were added. The reaction mixture was then refluxed for 5 hr under N₂ atmosphere. It was then poured over ice-water (30 ml) containing 1 ml of conc.HCl, extracted with CHCl₃ (3 X 10 ml) and dried (Na₂SO₄). Removal of solvent followed by recrystallization from CDCl₃ afforded the compound.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

N-[(3-Phenylsulfanyl-1-phenylsulfonyl-1H-indol-2- yl)methyl]propionamide top

Crystal data top

C₂₄H₂₂N₂O₃S₂	F(000) = 944
M_r = 450.56	D_x = 1.335 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9917 reflections
a = 10.9216 (3) Å	θ = 2.5–27.5°
b = 23.1856 (6) Å	µ = 0.27 mm⁻¹
c = 9.4298 (2) Å	T = 295 K
β = 110.147 (1)°	Block, colourless
V = 2241.74 (10) Å³	0.26 × 0.20 × 0.16 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	5543 independent reflections
Radiation source: fine-focus sealed tube	3962 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω and φ scans	θ_max = 28.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.934, T_max = 0.959	k = −30→30
26619 measured reflections	l = −12→12

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) = 0.117	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0466P)² + 0.7649P] where P = (F_o² + 2F_c²)/3
5543 reflections	(Δ/σ)_max < 0.001
281 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₄H₂₂N₂O₃S₂	V = 2241.74 (10) Å³
M_r = 450.56	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.9216 (3) Å	µ = 0.27 mm⁻¹
b = 23.1856 (6) Å	T = 295 K
c = 9.4298 (2) Å	0.26 × 0.20 × 0.16 mm
β = 110.147 (1)°

Data collection top

Bruker Kappa APEXII diffractometer	5543 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3962 reflections with I > 2σ(I)
T_min = 0.934, T_max = 0.959	R_int = 0.026
26619 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.04	Δρ_max = 0.22 e Å⁻³
5543 reflections	Δρ_min = −0.24 e Å⁻³
281 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.35657 (17)	0.09160 (9)	0.2609 (2)	0.0566 (5)
C2	0.3938 (2)	0.03731 (10)	0.3194 (3)	0.0700 (6)
H2	0.3548	0.0203	0.3824	0.084*
C3	0.4893 (2)	0.00865 (12)	0.2834 (3)	0.0863 (8)
H3	0.5157	−0.0279	0.3226	0.104*
C4	0.5455 (2)	0.03392 (15)	0.1901 (4)	0.0951 (9)
H4	0.6101	0.0144	0.1660	0.114*
C5	0.5080 (3)	0.08729 (16)	0.1321 (4)	0.1013 (9)
H5	0.5466	0.1039	0.0683	0.122*
C6	0.4135 (2)	0.11678 (12)	0.1672 (3)	0.0823 (7)
H6	0.3882	0.1534	0.1280	0.099*
C7	0.02638 (16)	0.12894 (7)	0.03684 (18)	0.0424 (4)
C8	−0.08307 (16)	0.09744 (7)	−0.02800 (17)	0.0408 (4)
C9	−0.08564 (16)	0.05099 (7)	0.07163 (18)	0.0400 (4)
C10	−0.17279 (18)	0.00610 (8)	0.0598 (2)	0.0505 (4)
H10	−0.2475	0.0026	−0.0252	0.061*
C11	−0.1468 (2)	−0.03292 (9)	0.1756 (3)	0.0603 (5)
H11	−0.2040	−0.0633	0.1690	0.072*
C12	−0.0360 (2)	−0.02736 (9)	0.3024 (2)	0.0621 (5)
H12	−0.0205	−0.0543	0.3798	0.075*
C13	0.0514 (2)	0.01642 (9)	0.3174 (2)	0.0562 (5)
H13	0.1255	0.0197	0.4033	0.067*
C14	0.02547 (16)	0.05580 (7)	0.19997 (18)	0.0421 (4)
C15	−0.31688 (17)	0.15356 (8)	−0.1635 (2)	0.0486 (4)
C16	−0.2896 (2)	0.18462 (9)	−0.0313 (2)	0.0581 (5)
H16	−0.2073	0.1826	0.0426	0.070*
C17	−0.3848 (3)	0.21854 (11)	−0.0095 (3)	0.0791 (7)
H17	−0.3663	0.2396	0.0794	0.095*
C18	−0.5068 (3)	0.22168 (13)	−0.1175 (4)	0.0935 (9)
H18	−0.5709	0.2444	−0.1013	0.112*
C19	−0.5334 (2)	0.19155 (13)	−0.2483 (4)	0.0920 (8)
H19	−0.6156	0.1942	−0.3222	0.110*
C20	−0.4396 (2)	0.15706 (10)	−0.2721 (3)	0.0703 (6)
H20	−0.4589	0.1361	−0.3613	0.084*
C21	0.0691 (2)	0.18028 (8)	−0.0289 (2)	0.0523 (4)
H21A	0.1634	0.1802	0.0017	0.063*
H21B	0.0340	0.1777	−0.1382	0.063*
C22	−0.0289 (2)	0.27564 (8)	−0.0787 (2)	0.0547 (5)
C23	−0.0686 (3)	0.32715 (9)	−0.0106 (2)	0.0770 (7)
H23A	−0.0868	0.3150	0.0786	0.092*
H23B	0.0043	0.3538	0.0219	0.092*
C24	−0.1833 (3)	0.35801 (12)	−0.1114 (3)	0.0908 (8)
H24A	−0.1677	0.3693	−0.2016	0.136*
H24B	−0.1990	0.3917	−0.0610	0.136*
H24C	−0.2581	0.3331	−0.1374	0.136*
N1	0.09434 (14)	0.10500 (6)	0.17978 (16)	0.0455 (3)
N2	0.02720 (17)	0.23387 (6)	0.01795 (16)	0.0538 (4)
H2A	0.0391	0.2389	0.1121	0.065*
O1	0.23581 (16)	0.10952 (8)	0.44854 (16)	0.0793 (5)
O2	0.24265 (16)	0.18788 (7)	0.2755 (2)	0.0806 (5)
O3	−0.04305 (18)	0.27293 (7)	−0.21278 (15)	0.0766 (5)
S1	0.23448 (5)	0.12841 (2)	0.30516 (6)	0.05906 (16)
S2	−0.20032 (5)	0.10989 (2)	−0.20547 (5)	0.05258 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0413 (9)	0.0629 (12)	0.0571 (11)	−0.0080 (8)	0.0062 (8)	−0.0097 (9)
C2	0.0551 (12)	0.0777 (15)	0.0703 (14)	0.0019 (11)	0.0128 (10)	0.0042 (11)
C3	0.0606 (14)	0.0838 (18)	0.105 (2)	0.0139 (13)	0.0163 (14)	−0.0022 (15)
C4	0.0519 (13)	0.119 (2)	0.117 (2)	0.0048 (15)	0.0318 (15)	−0.0191 (19)
C5	0.0679 (16)	0.122 (3)	0.128 (3)	−0.0041 (16)	0.0524 (17)	0.011 (2)
C6	0.0575 (13)	0.0840 (17)	0.108 (2)	−0.0058 (12)	0.0320 (14)	0.0118 (14)
C7	0.0488 (9)	0.0427 (9)	0.0380 (8)	0.0025 (7)	0.0179 (7)	−0.0070 (7)
C8	0.0447 (9)	0.0437 (9)	0.0352 (8)	0.0051 (7)	0.0150 (7)	−0.0045 (7)
C9	0.0434 (8)	0.0399 (8)	0.0405 (8)	0.0062 (7)	0.0194 (7)	−0.0052 (6)
C10	0.0478 (9)	0.0498 (10)	0.0569 (10)	−0.0007 (8)	0.0219 (8)	−0.0082 (8)
C11	0.0690 (13)	0.0462 (11)	0.0784 (14)	0.0009 (9)	0.0418 (11)	0.0024 (10)
C12	0.0798 (14)	0.0528 (11)	0.0636 (12)	0.0179 (10)	0.0373 (11)	0.0167 (9)
C13	0.0605 (11)	0.0618 (12)	0.0454 (10)	0.0146 (9)	0.0169 (8)	0.0075 (8)
C14	0.0443 (9)	0.0442 (9)	0.0400 (8)	0.0073 (7)	0.0172 (7)	−0.0042 (7)
C15	0.0503 (9)	0.0453 (10)	0.0469 (9)	0.0041 (8)	0.0128 (8)	0.0105 (8)
C16	0.0581 (11)	0.0572 (12)	0.0567 (11)	0.0122 (9)	0.0169 (9)	0.0004 (9)
C17	0.0856 (16)	0.0702 (15)	0.0843 (16)	0.0264 (13)	0.0331 (14)	0.0003 (12)
C18	0.0784 (17)	0.0898 (19)	0.114 (2)	0.0439 (15)	0.0348 (17)	0.0238 (17)
C19	0.0615 (14)	0.099 (2)	0.099 (2)	0.0263 (14)	0.0062 (14)	0.0286 (17)
C20	0.0635 (13)	0.0708 (14)	0.0622 (13)	0.0088 (11)	0.0034 (10)	0.0099 (11)
C21	0.0637 (11)	0.0505 (10)	0.0496 (10)	−0.0055 (9)	0.0284 (9)	−0.0068 (8)
C22	0.0824 (14)	0.0484 (10)	0.0374 (9)	−0.0075 (9)	0.0258 (9)	−0.0033 (8)
C23	0.130 (2)	0.0541 (12)	0.0471 (11)	0.0132 (13)	0.0308 (13)	−0.0022 (9)
C24	0.119 (2)	0.0855 (18)	0.0672 (15)	0.0240 (16)	0.0306 (15)	0.0015 (13)
N1	0.0438 (7)	0.0509 (8)	0.0388 (7)	−0.0017 (6)	0.0102 (6)	−0.0052 (6)
N2	0.0867 (12)	0.0439 (8)	0.0348 (7)	−0.0055 (8)	0.0259 (8)	−0.0049 (6)
O1	0.0732 (10)	0.1127 (13)	0.0419 (8)	0.0004 (9)	0.0070 (7)	−0.0195 (8)
O2	0.0718 (10)	0.0555 (9)	0.0969 (12)	−0.0100 (7)	0.0064 (9)	−0.0252 (8)
O3	0.1285 (14)	0.0722 (10)	0.0369 (7)	0.0096 (9)	0.0383 (8)	0.0020 (6)
S1	0.0518 (3)	0.0646 (3)	0.0511 (3)	−0.0045 (2)	0.0054 (2)	−0.0177 (2)
S2	0.0570 (3)	0.0629 (3)	0.0337 (2)	0.0058 (2)	0.01022 (18)	−0.00357 (19)

Geometric parameters (Å, º) top

C1—C6	1.374 (3)	C15—C16	1.380 (3)
C1—C2	1.378 (3)	C15—C20	1.381 (3)
C1—S1	1.750 (2)	C15—S2	1.7748 (19)
C2—C3	1.374 (3)	C16—C17	1.374 (3)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.366 (4)	C17—C18	1.372 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.358 (4)	C18—C19	1.358 (4)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.370 (4)	C19—C20	1.378 (4)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.354 (2)	C21—N2	1.445 (2)
C7—N1	1.410 (2)	C21—H21A	0.9700
C7—C21	1.489 (3)	C21—H21B	0.9700
C8—C9	1.436 (2)	C22—O3	1.222 (2)
C8—S2	1.7457 (16)	C22—N2	1.326 (2)
C9—C10	1.389 (2)	C22—C23	1.489 (3)
C9—C14	1.392 (2)	C23—C24	1.472 (3)
C10—C11	1.370 (3)	C23—H23A	0.9700
C10—H10	0.9300	C23—H23B	0.9700
C11—C12	1.383 (3)	C24—H24A	0.9600
C11—H11	0.9300	C24—H24B	0.9600
C12—C13	1.367 (3)	C24—H24C	0.9600
C12—H12	0.9300	N1—S1	1.6699 (14)
C13—C14	1.388 (2)	N2—H2A	0.8600
C13—H13	0.9300	O1—S1	1.4165 (17)
C14—N1	1.415 (2)	O2—S1	1.4159 (17)

C6—C1—C2	120.6 (2)	C15—C16—H16	120.2
C6—C1—S1	119.78 (18)	C18—C17—C16	120.7 (2)
C2—C1—S1	119.61 (18)	C18—C17—H17	119.7
C3—C2—C1	119.2 (2)	C16—C17—H17	119.7
C3—C2—H2	120.4	C19—C18—C17	119.8 (2)
C1—C2—H2	120.4	C19—C18—H18	120.1
C4—C3—C2	120.0 (3)	C17—C18—H18	120.1
C4—C3—H3	120.0	C18—C19—C20	120.5 (2)
C2—C3—H3	120.0	C18—C19—H19	119.7
C5—C4—C3	120.6 (3)	C20—C19—H19	119.7
C5—C4—H4	119.7	C19—C20—C15	120.0 (2)
C3—C4—H4	119.7	C19—C20—H20	120.0
C4—C5—C6	120.4 (3)	C15—C20—H20	120.0
C4—C5—H5	119.8	N2—C21—C7	112.51 (15)
C6—C5—H5	119.8	N2—C21—H21A	109.1
C5—C6—C1	119.2 (3)	C7—C21—H21A	109.1
C5—C6—H6	120.4	N2—C21—H21B	109.1
C1—C6—H6	120.4	C7—C21—H21B	109.1
C8—C7—N1	108.15 (15)	H21A—C21—H21B	107.8
C8—C7—C21	126.70 (16)	O3—C22—N2	122.52 (18)
N1—C7—C21	125.15 (15)	O3—C22—C23	122.38 (18)
C7—C8—C9	108.81 (14)	N2—C22—C23	115.06 (16)
C7—C8—S2	125.86 (14)	C24—C23—C22	114.89 (19)
C9—C8—S2	125.31 (13)	C24—C23—H23A	108.5
C10—C9—C14	119.86 (16)	C22—C23—H23A	108.5
C10—C9—C8	132.61 (16)	C24—C23—H23B	108.5
C14—C9—C8	107.52 (15)	C22—C23—H23B	108.5
C11—C10—C9	118.87 (18)	H23A—C23—H23B	107.5
C11—C10—H10	120.6	C23—C24—H24A	109.5
C9—C10—H10	120.6	C23—C24—H24B	109.5
C10—C11—C12	120.43 (19)	H24A—C24—H24B	109.5
C10—C11—H11	119.8	C23—C24—H24C	109.5
C12—C11—H11	119.8	H24A—C24—H24C	109.5
C13—C12—C11	122.05 (18)	H24B—C24—H24C	109.5
C13—C12—H12	119.0	C7—N1—C14	108.48 (13)
C11—C12—H12	119.0	C7—N1—S1	126.97 (12)
C12—C13—C14	117.57 (18)	C14—N1—S1	124.54 (12)
C12—C13—H13	121.2	C22—N2—C21	122.54 (15)
C14—C13—H13	121.2	C22—N2—H2A	118.7
C13—C14—C9	121.21 (17)	C21—N2—H2A	118.7
C13—C14—N1	131.79 (16)	O2—S1—O1	120.59 (11)
C9—C14—N1	107.00 (14)	O2—S1—N1	106.35 (9)
C16—C15—C20	119.43 (19)	O1—S1—N1	106.31 (9)
C16—C15—S2	123.45 (14)	O2—S1—C1	108.84 (11)
C20—C15—S2	117.10 (16)	O1—S1—C1	108.57 (10)
C17—C16—C15	119.7 (2)	N1—S1—C1	105.10 (8)
C17—C16—H16	120.2	C8—S2—C15	103.06 (8)

C6—C1—C2—C3	0.3 (3)	C16—C15—C20—C19	0.3 (3)
S1—C1—C2—C3	179.69 (18)	S2—C15—C20—C19	−178.15 (19)
C1—C2—C3—C4	−0.4 (4)	C8—C7—C21—N2	93.9 (2)
C2—C3—C4—C5	0.0 (4)	N1—C7—C21—N2	−85.7 (2)
C3—C4—C5—C6	0.4 (5)	O3—C22—C23—C24	32.6 (4)
C4—C5—C6—C1	−0.4 (5)	N2—C22—C23—C24	−149.7 (2)
C2—C1—C6—C5	0.0 (4)	C8—C7—N1—C14	2.10 (18)
S1—C1—C6—C5	−179.3 (2)	C21—C7—N1—C14	−178.23 (15)
N1—C7—C8—C9	−1.67 (18)	C8—C7—N1—S1	−179.39 (12)
C21—C7—C8—C9	178.66 (16)	C21—C7—N1—S1	0.3 (2)
N1—C7—C8—S2	179.76 (12)	C13—C14—N1—C7	178.38 (18)
C21—C7—C8—S2	0.1 (3)	C9—C14—N1—C7	−1.68 (17)
C7—C8—C9—C10	−178.64 (17)	C13—C14—N1—S1	−0.2 (3)
S2—C8—C9—C10	−0.1 (3)	C9—C14—N1—S1	179.76 (12)
C7—C8—C9—C14	0.63 (18)	O3—C22—N2—C21	−3.8 (3)
S2—C8—C9—C14	179.21 (12)	C23—C22—N2—C21	178.51 (19)
C14—C9—C10—C11	−0.3 (2)	C7—C21—N2—C22	−132.61 (19)
C8—C9—C10—C11	178.90 (17)	C7—N1—S1—O2	25.25 (18)
C9—C10—C11—C12	0.4 (3)	C14—N1—S1—O2	−156.46 (14)
C10—C11—C12—C13	−0.2 (3)	C7—N1—S1—O1	154.92 (15)
C11—C12—C13—C14	−0.1 (3)	C14—N1—S1—O1	−26.79 (16)
C12—C13—C14—C9	0.2 (3)	C7—N1—S1—C1	−90.08 (16)
C12—C13—C14—N1	−179.87 (18)	C14—N1—S1—C1	88.21 (15)
C10—C9—C14—C13	0.0 (2)	C6—C1—S1—O2	−19.4 (2)
C8—C9—C14—C13	−179.39 (15)	C2—C1—S1—O2	161.21 (16)
C10—C9—C14—N1	−179.96 (14)	C6—C1—S1—O1	−152.42 (18)
C8—C9—C14—N1	0.66 (17)	C2—C1—S1—O1	28.22 (19)
C20—C15—C16—C17	0.0 (3)	C6—C1—S1—N1	94.15 (19)
S2—C15—C16—C17	178.35 (17)	C2—C1—S1—N1	−85.20 (17)
C15—C16—C17—C18	0.2 (4)	C7—C8—S2—C15	−93.53 (16)
C16—C17—C18—C19	−0.8 (4)	C9—C8—S2—C15	88.13 (15)
C17—C18—C19—C20	1.1 (5)	C16—C15—S2—C8	20.21 (18)
C18—C19—C20—C15	−0.9 (4)	C20—C15—S2—C8	−161.43 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2	0.86	2.52	2.939 (2)	111
C6—H6···O2	0.93	2.57	2.925 (3)	103
C13—H13···O1	0.93	2.37	2.921 (3)	118
C21—H21A···O2	0.97	2.43	2.849 (3)	106
C21—H21B···O3	0.97	2.38	2.767 (2)	103
C18—H18···O2ⁱ	0.93	2.52	3.317 (3)	144
N2—H2A···O3ⁱⁱ	0.86	2.15	2.899 (2)	145
C16—H16···O3ⁱⁱ	0.93	2.60	3.416 (3)	147
C10—H10···Cg2ⁱⁱⁱ	0.93	2.81	3.658 (2)	152
C5—H5···Cg4^iv	0.93	2.91	3.788 (4)	158

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₂N₂O₃S₂
M_r	450.56
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	10.9216 (3), 23.1856 (6), 9.4298 (2)
β (°)	110.147 (1)
V (Å³)	2241.74 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.26 × 0.20 × 0.16

Data collection
Diffractometer	Bruker Kappa APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.934, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	26619, 5543, 3962
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.117, 1.04
No. of reflections	5543
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.24

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2	0.86	2.52	2.939 (2)	111
C6—H6···O2	0.93	2.57	2.925 (3)	103
C13—H13···O1	0.93	2.37	2.921 (3)	118
C21—H21A···O2	0.97	2.43	2.849 (3)	106
C21—H21B···O3	0.97	2.38	2.767 (2)	103
C18—H18···O2ⁱ	0.93	2.52	3.317 (3)	144
N2—H2A···O3ⁱⁱ	0.86	2.15	2.899 (2)	145
C16—H16···O3ⁱⁱ	0.93	2.60	3.416 (3)	147
C10—H10···Cg2ⁱⁱⁱ	0.93	2.81	3.658 (2)	152
C5—H5···Cg4^iv	0.93	2.91	3.788 (4)	158

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

Acknowledgements

The authors acknowledge SAIF, IIT Madras, for the data collection.

References

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