(7-Chloro-2-oxo-2H-chromen-4-yl)methyl piperidine-1-carbodithio­ate

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

doi:10.1107/S1600536812007933

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o878-o879

doi:10.1107/S1600536812007933

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(7-Chloro-2-oxo-2H-chromen-4-yl)methyl piperidine-1-carbodithioate

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

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

(Received 14 February 2012; accepted 22 February 2012; online 29 February 2012)

In the title compound, C₁₆H₁₆ClNO₂S₂, the piperidine ring is in a chair conformation. In the coumarin ring system, the dihedral angle between the benzene and pyran rings is 3.5 (1)°. In the crystal, a weak C—H⋯O hydrogen bond links molecules into chains along [001]. In addition, π–π stacking interactions are present involving the benzene and pyran rings, with a centroid-to-centroid distance of 3.712 (2) Å. The crystal studied is a nonmerohedral twin with refined components 0.221 (1) and 0.779 (1).

Related literature

For structures and properties of coumarins, see: Kulkarni et al. (2006 ); Jones et al. (1985 ); Trenor et al. (2004 ); Hung et al. (2007 ). For the applications of dithiocarbamate compounds, see: Bergendorff & Hansson (2002 ); Huang et al. (2009 ). For standard bond lengths, see: Allen et al. (1987 ). For ring conformations, see: Duax & Norton (1975 ). For the synthesis of the title compound, see: Shastri et al. (2004 ); Vasilliev & Polackov (2000 ).

Experimental

Crystal data

C₁₆H₁₆ClNO₂S₂
M_r = 353.87
Monoclinic, P c
a = 4.9427 (3) Å
b = 11.5010 (6) Å
c = 14.0006 (8) Å
β = 90.271 (6)°
V = 795.87 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.51 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.2 mm

Data collection

Oxford Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.886, T_max = 1.000
13944 measured reflections
2801 independent reflections
2678 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.082
S = 1.04
2801 reflections
200 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ), with 1394 Friedel pairs
Flack parameter: −0.01 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2ⁱ	0.93	2.41	3.167 (5)	139
Symmetry code: (i) $[x-1, -y+2, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO ; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); 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/S1600536812007933/lh5420sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007933/lh5420Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812007933/lh5420Isup3.cml

checkCIF report

Comment top

Coumarins are an important class of heterocycles, which are widespread in the plant kingdom and have been extensively reported. Coumarin derivatives with various substituents at the C-4 position have revealed potential as anti-microbial, anti-viral, anti-oxidant, anti-inflammatory and anti-cancer agents (Kulkarni et al., 2006). They have also found a place and subsequent use in laser dyes, non-linear optical chromophores, fluorescent whiteners, fluorescent probes and solar energy collectors due to their outstanding optical properties (Jones et al., 1985; Trenor et al., 2004; Hung et al., 2007). Dithiocarbamate (DTC) derivatives are valuable compounds due to their interesting chemistry and utility. These compounds have shown wide applications as pesticides, fungicides in agriculture, sulfur vulcanization and anti-cancer agents (Bergendorff & Hansson, 2002; Huang et al., 2009). In our work, we have been able to link a DTC moiety at C-4 methylene carbon and it was a thought of considerable interest to study the effect of this moiety on the total solid-state conformation of the molecule. A new series of piperidine-1-dithiocarbomate derivatives of 4-substituted coumarin was synthesized in a single step and screened for antimicrobial, anti-diabetic, DNA binding and DNA cleavage activity. In this paper we report the crystal structure of (7-Chloro-2-oxo-2H-chromen-4-yl)methyl piperidine-1-carbodithioate (I).

The molecular structure of (I) is shown in Fig. 1. The bond lengths (Allen et al., 1987) and angles in the molecule are within normal ranges. The pyridine ring adopts a normal chair conformation (asymmetry parameters: ΔC_s(C15—N1) = 0.94; ΔC₂(C16—C15) = 2.5 (Duax & Norton, 1975). The dihedral angle bewteen pyran and benzene rings in the coumarin moiety 3.5 (1)°. In the crystal, weak C—H···O hydrogen bonds link molecules along [001] (Fig. 2). In addition, π–π interactions between the pyran ring at (x, y, z) and the benzene ring at (1 + x, y, z) are present [centroid separation = 3.712 (2) Å, interplanar spacing = 3.407 Å and centroid shift = 1.47 Å].

Related literature top

For structures and properties of coumarins, see: Kulkarni et al. (2006); Jones et al.(1985); Trenor et al. (2004); Hung et al. (2007). For the applications of dithiocarbamate compounds, see: Bergendorff & Hansson (2002); Huang et al. (2009). For standard bond lengths, see: Allen et al. (1987). For ring conformations, see: Duax & Norton (1975). For the synthesis of the title compound, see: Shastri et al. (2004); Vasilliev & Polackov (2000).

Experimental top

4-Bromomethyl coumarin required for the synthesis of the target molecule was synthesized according to an already reported procedure (Shastri et al., 2004) involving the Pechmann cyclization of phenols with 4-Bromoethyl acetoacetate and the potassium salt of piperidine-1-dithiocarbomate was synthesized according to the procedure reported (Vasilliev & Polackov, 2000).

A mixture of 2.73 g (0.01 mol) of 7-chloro-4-bromomethyl coumarin and 1.99 g (0.01 mol) of potassium salt of piperidine-1-dithiocarbomate in 30 ml dry alcohol was stirred for 12 h 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, the solvent evaporated and recrystallized 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. 407–409 K. IR (KBr): 1720 cm-1 (C═O), 1430 cm-1 (C═S), 849 cm-1 (C—N), 771 cm-1 (C—Cl). GCMS: m/e: 353.03. 1H NMR (300 MHz, CdCl3, δ, p.p.m.): 2.81 (s, 4H, C13 & C17—H), 2.79 (s, 6H, C14, C16 & C16—H), 4.72 (s, 2H, C4—CH2), 6.21 (s, 1H, C3—H), 7.18 (d, 2H, C6 & C8—H), 7.47 (d, 1H C5—H). Elemental analysis: C, 54.27; H, 4.54; Cl, 10.00; N, 3.92; O, 9.01; S, 18.09.

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. Ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The packing arrangement of molecules viewed along the a axis. The broken lines show the intermolecular C—H···O interactions.

(7-Chloro-2-oxo-2H-chromen-4-yl)methyl piperidine-1-carbodithioate top

Crystal data top

C₁₆H₁₆ClNO₂S₂	F(000) = 368
M_r = 353.87	D_x = 1.477 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p -2yc	Cell parameters from 7572 reflections
a = 4.9427 (3) Å	θ = 3.4–29.0°
b = 11.5010 (6) Å	µ = 0.51 mm⁻¹
c = 14.0006 (8) Å	T = 293 K
β = 90.271 (6)°	Block, white
V = 795.87 (8) Å³	0.3 × 0.2 × 0.2 mm
Z = 2

Data collection top

Oxford Xcalibur Sapphire3 diffractometer	2801 independent reflections
Radiation source: fine-focus sealed tube	2678 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 16.1049 pixels mm^-1	θ_max = 25.0°, θ_min = 3.4°
ω scans	h = −5→5
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −13→13
T_min = 0.886, T_max = 1.000	l = −16→16
13944 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.082	w = 1/[σ²(F_o²) + (0.0367P)² + 0.3317P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2801 reflections	Δρ_max = 0.14 e Å⁻³
200 parameters	Δρ_min = −0.18 e Å⁻³
2 restraints	Absolute structure: Flack (1983), with 1394 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (10)

Crystal data top

C₁₆H₁₆ClNO₂S₂	V = 795.87 (8) Å³
M_r = 353.87	Z = 2
Monoclinic, Pc	Mo Kα radiation
a = 4.9427 (3) Å	µ = 0.51 mm⁻¹
b = 11.5010 (6) Å	T = 293 K
c = 14.0006 (8) Å	0.3 × 0.2 × 0.2 mm
β = 90.271 (6)°

Data collection top

Oxford Xcalibur Sapphire3 diffractometer	2801 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	2678 reflections with I > 2σ(I)
T_min = 0.886, T_max = 1.000	R_int = 0.047
13944 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.082	Δρ_max = 0.14 e Å⁻³
S = 1.04	Δρ_min = −0.18 e Å⁻³
2801 reflections	Absolute structure: Flack (1983), with 1394 Friedel pairs
200 parameters	Absolute structure parameter: −0.01 (10)
2 restraints

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 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 (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.1990 (2)	0.77560 (7)	0.36977 (7)	0.0421 (3)
S2	0.4685 (3)	0.60142 (9)	0.24062 (9)	0.0525 (3)
Cl1	−0.4816 (2)	1.27262 (9)	0.15209 (9)	0.0577 (3)
O1	0.2148 (6)	0.9922 (2)	0.03114 (17)	0.0429 (7)
C2	0.4260 (9)	0.9155 (3)	0.0384 (3)	0.0431 (10)
O2	0.5440 (8)	0.8931 (3)	−0.03402 (19)	0.0583 (9)
C3	0.4925 (9)	0.8712 (3)	0.1330 (3)	0.0373 (9)
H3	0.6290	0.8161	0.1393	0.045*
C4	0.3622 (8)	0.9077 (3)	0.2120 (2)	0.0328 (8)
C10	0.1525 (8)	0.9952 (3)	0.2026 (2)	0.0315 (8)
C5	0.0142 (9)	1.0460 (3)	0.2788 (2)	0.0362 (8)
H5	0.0531	1.0225	0.3410	0.043*
C6	−0.1802 (9)	1.1309 (3)	0.2633 (3)	0.0405 (10)
H6	−0.2696	1.1644	0.3147	0.049*
C7	−0.2409 (8)	1.1657 (3)	0.1707 (3)	0.0372 (9)
C8	−0.1117 (9)	1.1168 (3)	0.0933 (3)	0.0385 (9)
H8	−0.1538	1.1396	0.0313	0.046*
C9	0.0813 (8)	1.0334 (3)	0.1108 (2)	0.0354 (9)
C11	0.4485 (9)	0.8620 (3)	0.3081 (3)	0.0382 (9)
H11B	0.4967	0.9276	0.3484	0.046*
H11A	0.6100	0.8153	0.2998	0.046*
C12	0.2473 (9)	0.6313 (3)	0.3254 (3)	0.0378 (9)
N1	0.0894 (7)	0.5538 (3)	0.3692 (3)	0.0487 (9)
C17	−0.0804 (10)	0.5754 (4)	0.4518 (4)	0.0538 (12)
H17A	−0.2672	0.5577	0.4360	0.065*
H17B	−0.0697	0.6569	0.4694	0.065*
C16	0.0100 (13)	0.5010 (4)	0.5353 (4)	0.0637 (12)
H16A	−0.1126	0.5127	0.5884	0.076*
H16B	0.1891	0.5253	0.5557	0.076*
C15	0.0164 (14)	0.3726 (4)	0.5096 (4)	0.0732 (16)
H15A	−0.1668	0.3446	0.4997	0.088*
H15B	0.0962	0.3287	0.5618	0.088*
C14	0.1810 (12)	0.3540 (4)	0.4192 (4)	0.0719 (17)
H14B	0.3697	0.3712	0.4323	0.086*
H14A	0.1684	0.2731	0.4000	0.086*
C13	0.0825 (11)	0.4303 (3)	0.3383 (4)	0.0609 (14)
H13A	0.1971	0.4198	0.2829	0.073*
H13B	−0.1008	0.4087	0.3207	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0626 (7)	0.0293 (5)	0.0344 (5)	0.0036 (5)	0.0134 (5)	0.0018 (4)
S2	0.0701 (7)	0.0446 (6)	0.0429 (5)	0.0132 (5)	0.0119 (6)	−0.0038 (5)
Cl1	0.0600 (7)	0.0446 (6)	0.0686 (8)	0.0118 (5)	0.0082 (6)	0.0067 (5)
O1	0.0627 (18)	0.0443 (16)	0.0218 (12)	0.0010 (14)	0.0080 (13)	−0.0001 (11)
C2	0.064 (3)	0.0350 (19)	0.031 (2)	−0.003 (2)	0.0083 (19)	−0.0062 (16)
O2	0.083 (2)	0.0600 (19)	0.0322 (16)	0.0051 (18)	0.0230 (17)	−0.0058 (13)
C3	0.048 (2)	0.0316 (18)	0.0324 (19)	−0.0030 (18)	0.0071 (19)	−0.0001 (15)
C4	0.041 (2)	0.0289 (18)	0.0287 (19)	−0.0076 (15)	0.0040 (15)	0.0011 (14)
C10	0.040 (2)	0.0283 (18)	0.0258 (19)	−0.0056 (16)	0.0035 (15)	0.0010 (14)
C5	0.050 (2)	0.0362 (19)	0.0224 (17)	−0.0096 (19)	0.0046 (16)	−0.0007 (14)
C6	0.053 (3)	0.034 (2)	0.035 (2)	−0.0039 (18)	0.0123 (18)	−0.0036 (16)
C7	0.040 (2)	0.0297 (19)	0.042 (2)	−0.0062 (16)	0.0032 (18)	0.0033 (16)
C8	0.051 (3)	0.034 (2)	0.0305 (19)	−0.0055 (18)	0.0035 (18)	0.0056 (16)
C9	0.050 (2)	0.0311 (18)	0.0255 (18)	−0.0070 (17)	0.0069 (16)	−0.0014 (14)
C11	0.050 (3)	0.0372 (18)	0.0272 (19)	0.0007 (18)	0.0024 (17)	−0.0029 (16)
C12	0.049 (2)	0.034 (2)	0.0302 (19)	0.0047 (18)	−0.0042 (18)	0.0013 (15)
N1	0.061 (2)	0.0286 (16)	0.056 (2)	0.0022 (15)	0.006 (2)	0.0004 (15)
C17	0.060 (3)	0.037 (2)	0.064 (3)	−0.001 (2)	0.013 (2)	0.009 (2)
C16	0.076 (3)	0.055 (3)	0.060 (3)	−0.005 (3)	−0.005 (3)	0.012 (2)
C15	0.087 (4)	0.044 (2)	0.088 (4)	−0.011 (3)	−0.029 (4)	0.023 (3)
C14	0.070 (4)	0.034 (2)	0.112 (5)	0.001 (2)	−0.028 (4)	−0.003 (3)
C13	0.077 (4)	0.031 (2)	0.075 (3)	−0.003 (2)	0.006 (3)	−0.008 (2)

Geometric parameters (Å, º) top

S1—C12	1.788 (4)	C8—H8	0.9300
S1—C11	1.807 (4)	C11—H11B	0.9700
S2—C12	1.654 (4)	C11—H11A	0.9700
Cl1—C7	1.730 (4)	C12—N1	1.336 (5)
O1—C2	1.371 (5)	N1—C17	1.454 (5)
O1—C9	1.382 (4)	N1—C13	1.485 (5)
C2—O2	1.200 (4)	C17—C16	1.514 (6)
C2—C3	1.456 (5)	C17—H17A	0.9700
C3—C4	1.349 (5)	C17—H17B	0.9700
C3—H3	0.9300	C16—C15	1.521 (7)
C4—C10	1.450 (5)	C16—H16A	0.9700
C4—C11	1.505 (5)	C16—H16B	0.9700
C10—C5	1.398 (5)	C15—C14	1.524 (8)
C10—C9	1.402 (5)	C15—H15A	0.9700
C5—C6	1.386 (6)	C15—H15B	0.9700
C5—H5	0.9300	C14—C13	1.511 (7)
C6—C7	1.388 (5)	C14—H14B	0.9700
C6—H6	0.9300	C14—H14A	0.9700
C7—C8	1.380 (6)	C13—H13A	0.9700
C8—C9	1.374 (6)	C13—H13B	0.9700

C12—S1—C11	104.60 (18)	N1—C12—S1	112.4 (3)
C2—O1—C9	121.8 (3)	S2—C12—S1	122.2 (2)
O2—C2—O1	116.7 (4)	C12—N1—C17	126.3 (3)
O2—C2—C3	125.9 (4)	C12—N1—C13	121.2 (4)
O1—C2—C3	117.5 (3)	C17—N1—C13	112.5 (4)
C4—C3—C2	122.1 (4)	N1—C17—C16	110.4 (4)
C4—C3—H3	119.0	N1—C17—H17A	109.6
C2—C3—H3	119.0	C16—C17—H17A	109.6
C3—C4—C10	119.1 (3)	N1—C17—H17B	109.6
C3—C4—C11	119.3 (4)	C16—C17—H17B	109.6
C10—C4—C11	121.5 (3)	H17A—C17—H17B	108.1
C5—C10—C9	116.6 (3)	C17—C16—C15	111.8 (5)
C5—C10—C4	125.0 (3)	C17—C16—H16A	109.2
C9—C10—C4	118.5 (3)	C15—C16—H16A	109.2
C6—C5—C10	121.0 (3)	C17—C16—H16B	109.2
C6—C5—H5	119.5	C15—C16—H16B	109.2
C10—C5—H5	119.5	H16A—C16—H16B	107.9
C5—C6—C7	119.8 (4)	C16—C15—C14	110.2 (4)
C5—C6—H6	120.1	C16—C15—H15A	109.6
C7—C6—H6	120.1	C14—C15—H15A	109.6
C8—C7—C6	121.1 (4)	C16—C15—H15B	109.6
C8—C7—Cl1	119.5 (3)	C14—C15—H15B	109.6
C6—C7—Cl1	119.4 (3)	H15A—C15—H15B	108.1
C9—C8—C7	117.9 (4)	C13—C14—C15	111.7 (5)
C9—C8—H8	121.0	C13—C14—H14B	109.3
C7—C8—H8	121.0	C15—C14—H14B	109.3
C8—C9—O1	115.4 (3)	C13—C14—H14A	109.3
C8—C9—C10	123.6 (3)	C15—C14—H14A	109.3
O1—C9—C10	120.9 (3)	H14B—C14—H14A	107.9
C4—C11—S1	115.4 (3)	N1—C13—C14	109.3 (4)
C4—C11—H11B	108.4	N1—C13—H13A	109.8
S1—C11—H11B	108.4	C14—C13—H13A	109.8
C4—C11—H11A	108.4	N1—C13—H13B	109.8
S1—C11—H11A	108.4	C14—C13—H13B	109.8
H11B—C11—H11A	107.5	H13A—C13—H13B	108.3
N1—C12—S2	125.5 (3)

C9—O1—C2—O2	−173.5 (4)	C5—C10—C9—C8	0.5 (5)
C9—O1—C2—C3	4.7 (5)	C4—C10—C9—C8	−179.1 (4)
O2—C2—C3—C4	174.8 (4)	C5—C10—C9—O1	177.1 (3)
O1—C2—C3—C4	−3.2 (6)	C4—C10—C9—O1	−2.5 (5)
C2—C3—C4—C10	−1.1 (6)	C3—C4—C11—S1	−115.6 (4)
C2—C3—C4—C11	−177.6 (4)	C10—C4—C11—S1	68.0 (4)
C3—C4—C10—C5	−175.7 (4)	C12—S1—C11—C4	86.3 (3)
C11—C4—C10—C5	0.7 (5)	C11—S1—C12—N1	175.5 (3)
C3—C4—C10—C9	3.9 (5)	C11—S1—C12—S2	−3.6 (3)
C11—C4—C10—C9	−179.7 (3)	S2—C12—N1—C17	171.5 (4)
C9—C10—C5—C6	−0.9 (5)	S1—C12—N1—C17	−7.6 (5)
C4—C10—C5—C6	178.7 (4)	S2—C12—N1—C13	−5.4 (6)
C10—C5—C6—C7	0.5 (6)	S1—C12—N1—C13	175.4 (3)
C5—C6—C7—C8	0.3 (6)	C12—N1—C17—C16	−117.9 (5)
C5—C6—C7—Cl1	−179.4 (3)	C13—N1—C17—C16	59.3 (5)
C6—C7—C8—C9	−0.7 (6)	N1—C17—C16—C15	−55.2 (6)
Cl1—C7—C8—C9	179.0 (3)	C17—C16—C15—C14	52.2 (7)
C7—C8—C9—O1	−176.5 (3)	C16—C15—C14—C13	−53.3 (6)
C7—C8—C9—C10	0.3 (6)	C12—N1—C13—C14	117.5 (5)
C2—O1—C9—C8	175.0 (3)	C17—N1—C13—C14	−59.8 (6)
C2—O1—C9—C10	−1.9 (5)	C15—C14—C13—N1	56.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17B···S1	0.97	2.36	2.923 (5)	116
C13—H13A···S2	0.97	2.55	3.067 (4)	113
C6—H6···O2ⁱ	0.93	2.41	3.167 (5)	139

Symmetry code: (i) x−1, −y+2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆ClNO₂S₂
M_r	353.87
Crystal system, space group	Monoclinic, Pc
Temperature (K)	293
a, b, c (Å)	4.9427 (3), 11.5010 (6), 14.0006 (8)
β (°)	90.271 (6)
V (Å³)	795.87 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.51
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Oxford Xcalibur Sapphire3 diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.886, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13944, 2801, 2678
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.082, 1.04
No. of reflections	2801
No. of parameters	200
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.18
Absolute structure	Flack (1983), with 1394 Friedel pairs
Absolute structure parameter	−0.01 (10)

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
C6—H6···O2ⁱ	0.93	2.41	3.167 (5)	139

Symmetry code: (i) x−1, −y+2, z+1/2.

Acknowledgements

KMK is grateful to Karnatak Science College, Dharwad, for providing laboratory facilities. RK acknowledges the Department of Science and Technology for the single-crystal X-ray diffractometer, sanctioned as a National Facility under Project No. SR/S2/CMP-47/2003.

References

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