(2-Oxo-2H-benzo[h]chromen-4-yl)methyl morpholine-4-carbodithio­ate

Kant, R.; Gupta, V.K.; Kapoor, K.; Kour, G.; Kumar, K.M.; Mahabaleshwaraiah, N.M.; Kotresh, O.

doi:10.1107/S160053681201094X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o1104-o1105

doi:10.1107/S160053681201094X

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(2-Oxo-2H-benzo[h]chromen-4-yl)methyl morpholine-4-carbodithioate

Rajni Kant,^a ^* Vivek K. Gupta,^a Kamini Kapoor,^a Gurvinder Kour,^a K. Mahesh Kumar,^b N. M. Mahabaleshwaraiah ^b and O. Kotresh ^b

^aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and ^bDepartment of Chemistry, Karnatak Science College, Dharwad 580 001, Karnataka, India
^*Correspondence e-mail: rkvk.paper11@gmail.com

(Received 9 March 2012; accepted 13 March 2012; online 17 March 2012)

In the title compound, C₁₉H₁₇NO₃S₂, the morpholine ring is in a chair conformation. In the coumarin ring system, the dihedral angle between the benzene and pyran rings is 3.9 (1)°. In the crystal, weak C—H⋯O interactions link the molecules into corrugated layers parallel to (102). The crystal packing also exhibits π–π interactions, with distances of 3.644 (1) and 3.677 (1) Å between the centroids of the benzene rings of neighbouring molecules.

Related literature

For the biological activity of coumarins, see: Kontogiorgis & Hadjipavlou-Litina (2004 ). For a related structure, see: Kumar et al. (2012 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₉H₁₇NO₃S₂
M_r = 371.46
Monoclinic, P 2₁ /c
a = 13.0928 (4) Å
b = 11.6978 (3) Å
c = 11.3673 (3) Å
β = 99.232 (3)°
V = 1718.43 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.818, T_max = 1.000
18655 measured reflections
3017 independent reflections
2457 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.104
S = 1.05
3017 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O3ⁱ	0.93	2.42	3.346 (3)	173
C18—H18A⋯O2ⁱⁱ	0.97	2.56	3.466 (3)	155
Symmetry codes: (i) $[x-1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -z+2.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681201094X/cv5260sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201094X/cv5260Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201094X/cv5260Isup3.cml

checkCIF report

Comment top

Coumarins (2H-1-benzopyran-2-ones) form a distinct class of oxygen containing heterocycles and are widely distributed in nature. Coumarins represent a class of naturally and synthetically obtained compounds that possess a wide variety of biological activities. Specifically coumarins are reported to possess antiallergic, anticoagulant, antidiabetic activities and analgesic properties (Kontogiorgis & Hadjipavlou-Litina, 2004). In continuation of our interest on crystal structures study of coumarin derivatives (Kumar et al., 2012), we report the crystal structure of the title compound (I).

In (I) (Fig. 1), all bond lengths and angles are within normal ranges (Allen et al., 1987) and are in a good agreement with those in related structure (Kumar et al., 2012). The morpholine ring adopts a chair conformation. The dihedral angle bewteen the pyran and benzene rings in the coumarin fragment is 3.9 (1)°. Weak intermolecular C—H···O interactions (Table 1)link the molecules into corrugated layers parallel to (102) plane. The crystal packing exhibits π-π stacking interactions. The first of these is between the benzene ring C4/C5/C10-C13 and its symmetry-related partner at (1-x, 1-y, -z) with a distance of 3.644 (1) Å between the ring centroids. Another π-π interaction is between the benzene ring C4/C5/C10-C13 and the benzene ring C5-C10 at (1-x, 1-y,-z) with a distance of 3.677 (1) Å between the ring centroids.

Related literature top

For the biological activity of coumarins, see: Kontogiorgis & Hadjipavlou-Litina (2004). For a related structure, see: Kumar et al. (2012). For standard bond lengths, see: Allen et al. (1987).

Experimental top

A mixture of 2.73g (0.01 mol) of 7,8-benzo- 4-bromomethyl coumarin and 2.00g (0.01 mol) of potassium salt of morpholine-1-dithiocarbomate in 30 ml dry alcohol was stirrer for 12 hours at room temperature (the reaction was monitored by TLC). The solvent was evaporated and the solid was extracted twice with MDC –water mixture. The organic solvent was dried over CaCl2, evaporated the solvent and recrystallised from ethanol-chloroform. A slow evaporation technique was used to grow crystals suitable for diffraction studies in an ethanol-chloroform mixture. Yield=89%, m.p.-182-84oC. IR(KBr): 1717cm-1(C=O), 1423.8cm-1 (C=S), 849cm-1(C-N), 1111.7 (C-O-C).GCMS: m/e: 371.06. 1H- NMR(300MHz, CdCl3,δppm):2.81(s, 4H, C13 & C17-H), 1.73(s, 8H, C16,C17, C18 & C19-H), 4.32 (s,2H, C4-CH2), 7.26 (s,1H, C2-H), 7.45 (d,1H, C12-H), 7.63 (t,1H, C11-H), 7.66 (t,1H, C8-H), 7.91 (d,1H, C7-H), 7.97 (d,1H, C9-H), 8.47 (d,1H C6-H).Elemental analysis: C, 61.40; H, 4.56; N, 3.73; O, 12.90; S, 16.8 M.P.:

Structure description top

For the biological activity of coumarins, see: Kontogiorgis & Hadjipavlou-Litina (2004). For a related structure, see: Kumar et al. (2012). For standard bond lengths, see: Allen et al. (1987).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.

(2-Oxo-2H-benzo[h]chromen-4-yl)methyl morpholine-4-carbodithioate top

Crystal data top

C₁₉H₁₇NO₃S₂	F(000) = 776
M_r = 371.46	D_x = 1.436 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9000 reflections
a = 13.0928 (4) Å	θ = 3.5–29.0°
b = 11.6978 (3) Å	µ = 0.33 mm⁻¹
c = 11.3673 (3) Å	T = 293 K
β = 99.232 (3)°	Plate shaped, light yellow
V = 1718.43 (8) Å³	0.3 × 0.2 × 0.1 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3017 independent reflections
Radiation source: fine-focus sealed tube	2457 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 16.1049 pixels mm^-1	θ_max = 25.0°, θ_min = 3.5°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −13→13
T_min = 0.818, T_max = 1.000	l = −13→13
18655 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0471P)² + 0.803P] where P = (F_o² + 2F_c²)/3
3017 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₉H₁₇NO₃S₂	V = 1718.43 (8) Å³
M_r = 371.46	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.0928 (4) Å	µ = 0.33 mm⁻¹
b = 11.6978 (3) Å	T = 293 K
c = 11.3673 (3) Å	0.3 × 0.2 × 0.1 mm
β = 99.232 (3)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3017 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	2457 reflections with I > 2σ(I)
T_min = 0.818, T_max = 1.000	R_int = 0.034
18655 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.05	Δρ_max = 0.32 e Å⁻³
3017 reflections	Δρ_min = −0.19 e Å⁻³
226 parameters

Special details top

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
S1	0.85592 (4)	0.20784 (5)	0.78872 (5)	0.04418 (18)
S2	0.82222 (5)	0.40595 (6)	0.61667 (6)	0.0577 (2)
O1	0.74719 (10)	0.50873 (12)	1.10256 (12)	0.0393 (3)
O2	0.90505 (12)	0.56115 (14)	1.08171 (15)	0.0528 (4)
O3	1.20360 (13)	0.26933 (17)	0.65798 (18)	0.0683 (5)
N1	0.98691 (14)	0.26938 (16)	0.65122 (16)	0.0461 (5)
C1	0.74297 (15)	0.35148 (17)	0.91788 (17)	0.0359 (5)
C2	0.82708 (16)	0.41668 (18)	0.95188 (18)	0.0399 (5)
H2	0.8838	0.4079	0.9128	0.048*
C3	0.83295 (16)	0.49940 (18)	1.04603 (19)	0.0392 (5)
C4	0.66310 (15)	0.43868 (17)	1.07426 (18)	0.0342 (4)
C5	0.58582 (15)	0.45029 (18)	1.14826 (18)	0.0375 (5)
C6	0.59575 (18)	0.5245 (2)	1.2473 (2)	0.0478 (6)
H6	0.6539	0.5708	1.2654	0.057*
C7	0.5195 (2)	0.5279 (2)	1.3166 (2)	0.0594 (7)
H7	0.5270	0.5758	1.3828	0.071*
C8	0.4307 (2)	0.4611 (2)	1.2901 (2)	0.0594 (7)
H8	0.3795	0.4654	1.3379	0.071*
C9	0.41879 (17)	0.3897 (2)	1.1947 (2)	0.0523 (6)
H9	0.3592	0.3456	1.1776	0.063*
C10	0.49592 (15)	0.38159 (18)	1.12088 (19)	0.0405 (5)
C11	0.48607 (16)	0.30730 (19)	1.0208 (2)	0.0460 (5)
H11	0.4257	0.2650	1.0002	0.055*
C12	0.56292 (16)	0.29700 (19)	0.9549 (2)	0.0426 (5)
H12	0.5549	0.2463	0.8910	0.051*
C13	0.65541 (15)	0.36174 (17)	0.98100 (18)	0.0346 (4)
C14	0.73585 (16)	0.2666 (2)	0.8168 (2)	0.0455 (5)
H14A	0.7022	0.3037	0.7445	0.055*
H14B	0.6916	0.2040	0.8334	0.055*
C15	0.89538 (16)	0.29882 (18)	0.67899 (18)	0.0389 (5)
C16	1.03585 (19)	0.3310 (3)	0.5620 (2)	0.0592 (7)
H16A	0.9953	0.3981	0.5349	0.071*
H16B	1.0386	0.2820	0.4937	0.071*
C17	1.1420 (2)	0.3656 (3)	0.6158 (3)	0.0657 (7)
H17A	1.1743	0.4058	0.5568	0.079*
H17B	1.1385	0.4175	0.6815	0.079*
C18	1.15784 (19)	0.2117 (2)	0.7477 (2)	0.0595 (7)
H18A	1.1555	0.2632	0.8142	0.071*
H18B	1.2004	0.1466	0.7770	0.071*
C19	1.05149 (17)	0.1718 (2)	0.7007 (2)	0.0521 (6)
H19A	1.0540	0.1152	0.6389	0.063*
H19B	1.0213	0.1364	0.7642	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0474 (3)	0.0374 (3)	0.0509 (3)	0.0035 (2)	0.0176 (3)	−0.0012 (2)
S2	0.0595 (4)	0.0539 (4)	0.0601 (4)	0.0195 (3)	0.0114 (3)	0.0097 (3)
O1	0.0370 (8)	0.0371 (8)	0.0459 (8)	−0.0050 (6)	0.0130 (6)	−0.0069 (6)
O2	0.0448 (9)	0.0505 (10)	0.0661 (11)	−0.0162 (8)	0.0178 (8)	−0.0156 (8)
O3	0.0451 (10)	0.0716 (13)	0.0908 (13)	0.0030 (9)	0.0190 (9)	0.0225 (11)
N1	0.0415 (10)	0.0494 (11)	0.0487 (11)	0.0067 (9)	0.0109 (8)	0.0093 (9)
C1	0.0365 (11)	0.0320 (11)	0.0400 (11)	0.0015 (9)	0.0087 (9)	−0.0001 (9)
C2	0.0394 (12)	0.0378 (12)	0.0455 (12)	−0.0019 (10)	0.0159 (9)	−0.0023 (9)
C3	0.0372 (11)	0.0357 (11)	0.0466 (12)	−0.0024 (10)	0.0124 (9)	0.0001 (9)
C4	0.0310 (10)	0.0299 (10)	0.0423 (11)	0.0002 (8)	0.0074 (9)	0.0047 (9)
C5	0.0363 (11)	0.0339 (11)	0.0434 (11)	0.0075 (9)	0.0101 (9)	0.0071 (9)
C6	0.0471 (13)	0.0464 (13)	0.0523 (13)	0.0020 (11)	0.0157 (11)	−0.0034 (11)
C7	0.0645 (17)	0.0640 (17)	0.0547 (15)	0.0105 (14)	0.0241 (12)	−0.0039 (12)
C8	0.0524 (15)	0.0662 (17)	0.0668 (17)	0.0141 (13)	0.0317 (13)	0.0105 (14)
C9	0.0368 (12)	0.0556 (15)	0.0679 (16)	0.0036 (11)	0.0184 (11)	0.0114 (13)
C10	0.0320 (11)	0.0395 (12)	0.0513 (13)	0.0073 (9)	0.0104 (9)	0.0111 (10)
C11	0.0314 (11)	0.0433 (13)	0.0631 (15)	−0.0039 (10)	0.0066 (10)	0.0032 (11)
C12	0.0373 (11)	0.0397 (12)	0.0505 (12)	−0.0032 (10)	0.0059 (9)	−0.0035 (10)
C13	0.0313 (10)	0.0315 (10)	0.0412 (11)	0.0013 (9)	0.0062 (8)	0.0034 (9)
C14	0.0392 (12)	0.0473 (13)	0.0521 (13)	−0.0058 (10)	0.0142 (10)	−0.0126 (10)
C15	0.0411 (12)	0.0394 (12)	0.0365 (11)	0.0011 (9)	0.0076 (9)	−0.0043 (9)
C16	0.0541 (15)	0.0763 (18)	0.0482 (14)	0.0025 (13)	0.0117 (11)	0.0168 (13)
C17	0.0595 (16)	0.0668 (18)	0.0714 (17)	−0.0074 (14)	0.0129 (13)	0.0187 (14)
C18	0.0513 (15)	0.0550 (16)	0.0717 (16)	0.0093 (12)	0.0079 (12)	0.0117 (13)
C19	0.0487 (14)	0.0452 (14)	0.0657 (15)	0.0080 (11)	0.0193 (12)	0.0051 (11)

Geometric parameters (Å, º) top

S1—C15	1.778 (2)	C7—H7	0.9300
S1—C14	1.791 (2)	C8—C9	1.358 (4)
S2—C15	1.665 (2)	C8—H8	0.9300
O1—C4	1.369 (2)	C9—C10	1.416 (3)
O1—C3	1.385 (2)	C9—H9	0.9300
O2—C3	1.206 (2)	C10—C11	1.421 (3)
O3—C17	1.422 (3)	C11—C12	1.353 (3)
O3—C18	1.432 (3)	C11—H11	0.9300
N1—C15	1.333 (3)	C12—C13	1.419 (3)
N1—C16	1.472 (3)	C12—H12	0.9300
N1—C19	1.477 (3)	C14—H14A	0.9700
C1—C2	1.344 (3)	C14—H14B	0.9700
C1—C13	1.452 (3)	C16—C17	1.482 (3)
C1—C14	1.511 (3)	C16—H16A	0.9700
C2—C3	1.436 (3)	C16—H16B	0.9700
C2—H2	0.9300	C17—H17A	0.9700
C4—C13	1.382 (3)	C17—H17B	0.9700
C4—C5	1.422 (3)	C18—C19	1.484 (3)
C5—C6	1.411 (3)	C18—H18A	0.9700
C5—C10	1.418 (3)	C18—H18B	0.9700
C6—C7	1.369 (3)	C19—H19A	0.9700
C6—H6	0.9300	C19—H19B	0.9700
C7—C8	1.392 (4)

C15—S1—C14	104.92 (11)	C11—C12—C13	121.5 (2)
C4—O1—C3	121.69 (16)	C11—C12—H12	119.3
C17—O3—C18	109.50 (18)	C13—C12—H12	119.3
C15—N1—C16	122.97 (19)	C4—C13—C12	117.56 (18)
C15—N1—C19	126.25 (18)	C4—C13—C1	117.83 (18)
C16—N1—C19	110.76 (18)	C12—C13—C1	124.60 (19)
C2—C1—C13	119.11 (19)	C1—C14—S1	116.03 (15)
C2—C1—C14	122.65 (18)	C1—C14—H14A	108.3
C13—C1—C14	118.24 (18)	S1—C14—H14A	108.3
C1—C2—C3	122.69 (19)	C1—C14—H14B	108.3
C1—C2—H2	118.7	S1—C14—H14B	108.3
C3—C2—H2	118.7	H14A—C14—H14B	107.4
O2—C3—O1	116.48 (19)	N1—C15—S2	124.86 (16)
O2—C3—C2	126.85 (19)	N1—C15—S1	112.65 (15)
O1—C3—C2	116.66 (18)	S2—C15—S1	122.47 (12)
O1—C4—C13	121.80 (17)	N1—C16—C17	109.4 (2)
O1—C4—C5	115.18 (18)	N1—C16—H16A	109.8
C13—C4—C5	123.01 (19)	C17—C16—H16A	109.8
C6—C5—C10	119.38 (19)	N1—C16—H16B	109.8
C6—C5—C4	123.2 (2)	C17—C16—H16B	109.8
C10—C5—C4	117.41 (19)	H16A—C16—H16B	108.2
C7—C6—C5	119.7 (2)	O3—C17—C16	111.5 (2)
C7—C6—H6	120.2	O3—C17—H17A	109.3
C5—C6—H6	120.2	C16—C17—H17A	109.3
C6—C7—C8	121.3 (2)	O3—C17—H17B	109.3
C6—C7—H7	119.4	C16—C17—H17B	109.3
C8—C7—H7	119.4	H17A—C17—H17B	108.0
C9—C8—C7	120.2 (2)	O3—C18—C19	111.5 (2)
C9—C8—H8	119.9	O3—C18—H18A	109.3
C7—C8—H8	119.9	C19—C18—H18A	109.3
C8—C9—C10	120.8 (2)	O3—C18—H18B	109.3
C8—C9—H9	119.6	C19—C18—H18B	109.3
C10—C9—H9	119.6	H18A—C18—H18B	108.0
C9—C10—C5	118.6 (2)	N1—C19—C18	110.0 (2)
C9—C10—C11	122.2 (2)	N1—C19—H19A	109.7
C5—C10—C11	119.20 (19)	C18—C19—H19A	109.7
C12—C11—C10	121.2 (2)	N1—C19—H19B	109.7
C12—C11—H11	119.4	C18—C19—H19B	109.7
C10—C11—H11	119.4	H19A—C19—H19B	108.2

C13—C1—C2—C3	−2.1 (3)	C5—C4—C13—C12	3.8 (3)
C14—C1—C2—C3	178.4 (2)	O1—C4—C13—C1	4.1 (3)
C4—O1—C3—O2	−176.30 (18)	C5—C4—C13—C1	−175.22 (18)
C4—O1—C3—C2	3.2 (3)	C11—C12—C13—C4	−2.0 (3)
C1—C2—C3—O2	−179.9 (2)	C11—C12—C13—C1	177.0 (2)
C1—C2—C3—O1	0.7 (3)	C2—C1—C13—C4	−0.2 (3)
C3—O1—C4—C13	−5.7 (3)	C14—C1—C13—C4	179.26 (19)
C3—O1—C4—C5	173.65 (17)	C2—C1—C13—C12	−179.2 (2)
O1—C4—C5—C6	−2.7 (3)	C14—C1—C13—C12	0.3 (3)
C13—C4—C5—C6	176.6 (2)	C2—C1—C14—S1	27.7 (3)
O1—C4—C5—C10	178.51 (17)	C13—C1—C14—S1	−151.80 (16)
C13—C4—C5—C10	−2.2 (3)	C15—S1—C14—C1	−92.49 (18)
C10—C5—C6—C7	1.0 (3)	C16—N1—C15—S2	1.3 (3)
C4—C5—C6—C7	−177.8 (2)	C19—N1—C15—S2	−177.02 (18)
C5—C6—C7—C8	−1.3 (4)	C16—N1—C15—S1	179.49 (18)
C6—C7—C8—C9	0.7 (4)	C19—N1—C15—S1	1.2 (3)
C7—C8—C9—C10	0.2 (4)	C14—S1—C15—N1	177.39 (16)
C8—C9—C10—C5	−0.4 (3)	C14—S1—C15—S2	−4.34 (16)
C8—C9—C10—C11	179.6 (2)	C15—N1—C16—C17	126.5 (2)
C6—C5—C10—C9	−0.1 (3)	C19—N1—C16—C17	−55.0 (3)
C4—C5—C10—C9	178.67 (19)	C18—O3—C17—C16	−60.7 (3)
C6—C5—C10—C11	179.8 (2)	N1—C16—C17—O3	58.7 (3)
C4—C5—C10—C11	−1.4 (3)	C17—O3—C18—C19	59.6 (3)
C9—C10—C11—C12	−176.9 (2)	C15—N1—C19—C18	−127.2 (2)
C5—C10—C11—C12	3.2 (3)	C16—N1—C19—C18	54.3 (3)
C10—C11—C12—C13	−1.5 (3)	O3—C18—C19—N1	−56.7 (3)
O1—C4—C13—C12	−176.88 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O3ⁱ	0.93	2.42	3.346 (3)	173
C18—H18A···O2ⁱⁱ	0.97	2.56	3.466 (3)	155

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇NO₃S₂
M_r	371.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.0928 (4), 11.6978 (3), 11.3673 (3)
β (°)	99.232 (3)
V (Å³)	1718.43 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.3 × 0.2 × 0.1

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.818, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	18655, 3017, 2457
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.104, 1.05
No. of reflections	3017
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.19

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O3ⁱ	0.93	2.42	3.346 (3)	173
C18—H18A···O2ⁱⁱ	0.97	2.56	3.466 (3)	155

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

Acknowledgements

RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003. He is also thankful to the University of Jammu, Jammu, India, for financial support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
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Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar