4-Benzyl-2-(4-chloro­benzyl­idene)-3,4-di­hydro-2H-1,4-benzo­thia­zin-3(4H)-one

Ellouz, M.; Sebbar, N.K.; Essassi, E.M.; Ouzidan, Y.; Mague, J.T.; Zouihri, H.

doi:10.1107/S2414314616007641

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 5| May 2016| x160764

doi:10.1107/S2414314616007641

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4-Benzyl-2-(4-chlorobenzylidene)-3,4-dihydro-2H-1,4-benzothiazin-3(4H)-one

Mohamed Ellouz,^a Nada Kheira Sebbar,^a El Mokhtar Essassi,^a Younes Ouzidan,^b Joel T. Mague ^c and Hafid Zouihri ^d ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Mohammed V University in Rabat, BP 1014, Avenue Ibn Batouta, Rabat, Morocco, ^bLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Iimmouzzer, BP 2202, Fez, Morocco, ^cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, and ^dLaboratoire d'Ingénierie des Matériaux et d'Environnement: Modélisation et Application (LIMEMA), Ibn Tofail University, Kénitra, Morocco
^*Correspondence e-mail: hafid.zouihri@gmail.com

Edited by E. R. T. Tiekink, Sunway University, Malaysia (Received 6 April 2016; accepted 7 May 2016; online 13 May 2016)

The title compound, C₂₂H₁₆ClNOS, has three aromatic systems, viz. (i) a phenyl ring, (ii) a chlorobenzene ring and (iii) a 1,4-benzothiazine fused-ring system (r.m.s. deviation of the ten fitted atoms = 0.023 Å). The dihedral angle between planes (ii) and (iii) is 1.68 (8)°, indicating a coplanar arrangement, and between plane (i) and each of (ii) and (iii) is 85.61 (8) and 86.74 (8)°, respectively, indicating the phenyl ring is approximately perpendicular to the remaining residue. In the crystal, pairwise methylene-C—H⋯O(carbonyl) hydrogen bonds form dimers which stack along the b-axis direction.

Keywords: crystal structure; 1,4-benzothiazine derivatives; hydrogen bonds.

CCDC reference: 1478623

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Chemical scheme

Structure description

Several sulfur- and nitrogen-containing heterocyclic compounds have been well studied. Various 1,4-benzothiazine derivatives have been synthesized by several methods (Parai & Panda, 2009 ; Barange et al., 2007 ; Saadouni et al., 2014 ). 1,4-Benzothiazine derivatives are important because of their interesting biological properties such as anti-bacterial (Guarda et al., 2003 ; Sabatini et al., 2008 ), anti-fungal (Schiaffella et al., 2006 ; Gupta & Wagh, 2006 ), anti-hypertensive (Cecchetti et al., 2000 ) and anti-inflammatory (Kaneko et al., 2002 ) activities. As a continuation of our research devoted to the development of substituted 1,4-benzothiazine derivatives (Ellouz et al., 2015 ; Sebbar et al., 2015 ), we report here the synthesis of the title compound by reaction of benzyl chloride with 2-(4-chlorobenzylidene)-3,4-dihydro-2H-1,4-benzothiazin-3-one and potassium carbonate in the presence of tetra-n-butylammonium bromide (as catalyst).

In the title compound (Fig. 1), a Cremer–Pople analysis of the conformation of the heterocyclic ring gave puckering parameters Q = 0.095 (15) Å, θ = 69.3 (9)° and φ = 233.6 (9)°. In the crystal, pairwise C16—H16B⋯O1(−x + 1, −y + 2, −z + 1) hydrogen bonds form dimers which stack along the b-axis direction (Table 1 and Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16B⋯O1ⁱ	0.99	2.43	3.271 (2)	142
Symmetry code: (i) -x+1, -y+2, -z+1.

Figure 1
The molecular structure of the title compound, showing the atom numbering. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
The crystal packing of the title compound, viewed along the b axis. Intermolecular hydrogen bonds (see Table 2

) are shown as dashed lines.

Synthesis and crystallization

To a solution of 2-(4-chlorobenzylidene)-3,4-dihydro-2H-1,4-benzothiazin-3-one (0.944 g, 3.29 mmol), benzyl chloride (0.76 ml, 6.58 mmol) and potassium carbonate (0.91 g, 6.58 mmol) in DMF (15 ml) was added a catalytic amount of tetra-n-butylammonium bromide (0.11 g, 0.33 mmol). The mixture was stirred for 24 h. The solid material was removed by filtration and the solvent evaporated under vacuum. The solid product was purified by recrystallization from ethanol to afford colourless crystals in 80% yield.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Owing to poor agreement, on reflection, i.e. (1 1 7), was omitted from the final cycles of refinement.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₂H₁₆ClNOS
M_r	377.87
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	11.8931 (11), 6.5358 (6), 22.817 (2)
β (°)	93.239 (1)
V (Å³)	1770.7 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.35
Crystal size (mm)	0.33 × 0.18 × 0.13

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.84, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	32976, 4771, 3718
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.132, 1.12
No. of reflections	4771
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.01, −0.47
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015 ), SHELXL2014 (Sheldrick, 2015a), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1478623

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616007641/tk4010sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616007641/tk4010Isup2.hkl

checkCIF report

Experimental top

Structure description top

Several sulfur- and nitrogen-containing heterocyclic compounds have been well studied. Various 1,4-benzothiazine derivatives have been synthesized by several methods (Parai & Panda, 2009; Barange et al., 2007; Saadouni et al., 2014). 1,4-Benzothiazine derivatives are important because of their interesting biological properties such as anti-bacterial (Guarda et al., 2003; Sabatini et al., 2008), anti-fungal (Schiaffella et al., 2006; Gupta & Wagh, 2006), anti-hypertensive (Cecchetti et al., 2000) and anti-inflammatory (Kaneko et al., 2002) activities. As a continuation of our research devoted to the development of substituted 1,4-benzothiazine derivatives (Ellouz et al., 2015; Sebbar et al., 2015), we report here the synthesis of the title compound by reaction of benzyl chloride with 2-(4-chlorobenzylidene)-3,4-dihydro-2H-1,4-benzothiazin-3-one and potassium carbonate in the presence of tetra-n-butylammonium bromide (as catalyst).

In the title compound (Fig. 1), a Cremer–Pople analysis of the conformation of the heterocyclic ring gave puckering parameters Q = 0.095 (15) Å, θ = 69.3 (9)° and φ = 233.6 (9)°. In the crystal, pairwise C16—H16B···O1(-x + 1, -y + 2, -z + 1) hydrogen bonds form dimers which stack along the b-axis direction (Table 1 and Fig. 2).

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015a); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom numbering. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis. Intermolecular hydrogen bonds (see Table 2) are shown as dashed lines.

(2Z)-4-Benzyl-[(4-chlorophenyl)methylidene]-3,4-dihydro-2H-1,4-benzothiazin-3(4H)-one top

Crystal data top

C₂₂H₁₆ClNOS	F(000) = 784
M_r = 377.87	D_x = 1.417 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.8931 (11) Å	Cell parameters from 9932 reflections
b = 6.5358 (6) Å	θ = 3.1–29.1°
c = 22.817 (2) Å	µ = 0.35 mm⁻¹
β = 93.239 (1)°	T = 150 K
V = 1770.7 (3) Å³	Column, colourless
Z = 4	0.33 × 0.18 × 0.13 mm

Data collection top

Bruker SMART APEX CCD diffractometer	4771 independent reflections
Radiation source: fine-focus sealed tube	3718 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 8.3333 pixels mm^-1	θ_max = 29.2°, θ_min = 1.8°
φ and ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −8→8
T_min = 0.84, T_max = 0.96	l = −31→31
32976 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0782P)² + 0.0974P] where P = (F_o² + 2F_c²)/3
4771 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 1.01 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₂₂H₁₆ClNOS	V = 1770.7 (3) Å³
M_r = 377.87	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.8931 (11) Å	µ = 0.35 mm⁻¹
b = 6.5358 (6) Å	T = 150 K
c = 22.817 (2) Å	0.33 × 0.18 × 0.13 mm
β = 93.239 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	4771 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2016)	3718 reflections with I > 2σ(I)
T_min = 0.84, T_max = 0.96	R_int = 0.047
32976 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.12	Δρ_max = 1.01 e Å⁻³
4771 reflections	Δρ_min = −0.47 e Å⁻³
235 parameters

Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, collected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 10 sec/frame.

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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å). All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

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

	x	y	z	U_iso*/U_eq
Cl1	0.15276 (4)	−0.28012 (7)	0.65534 (2)	0.03513 (14)
S1	0.46828 (4)	0.63594 (7)	0.70652 (2)	0.02992 (13)
O1	0.53363 (10)	0.75024 (19)	0.54228 (5)	0.0313 (3)
N1	0.57084 (10)	0.9526 (2)	0.62091 (5)	0.0209 (3)
C1	0.54418 (13)	0.8579 (2)	0.72363 (7)	0.0224 (3)
C2	0.56174 (14)	0.8979 (3)	0.78364 (7)	0.0283 (4)
H2	0.5347	0.8045	0.8115	0.034*
C3	0.61815 (15)	1.0723 (3)	0.80268 (8)	0.0327 (4)
H3	0.6295	1.0995	0.8435	0.039*
C4	0.65809 (14)	1.2075 (3)	0.76201 (8)	0.0321 (4)
H4	0.6965	1.3282	0.7749	0.039*
C5	0.64220 (13)	1.1672 (3)	0.70240 (8)	0.0264 (3)
H5	0.6708	1.2603	0.6749	0.032*
C6	0.58483 (12)	0.9922 (2)	0.68203 (7)	0.0211 (3)
C7	0.52600 (13)	0.7785 (2)	0.59501 (7)	0.0218 (3)
C8	0.46567 (12)	0.6241 (2)	0.63034 (7)	0.0207 (3)
C9	0.40940 (13)	0.4769 (2)	0.59899 (7)	0.0221 (3)
H9	0.4121	0.4924	0.5577	0.026*
C10	0.34533 (12)	0.2989 (2)	0.61653 (7)	0.0218 (3)
C11	0.33017 (14)	0.2371 (3)	0.67448 (7)	0.0265 (3)
H11	0.3612	0.3173	0.7061	0.032*
C12	0.27024 (14)	0.0599 (3)	0.68625 (7)	0.0275 (4)
H12	0.2598	0.0205	0.7256	0.033*
C13	0.22615 (13)	−0.0581 (3)	0.64020 (8)	0.0255 (3)
C14	0.24071 (14)	−0.0036 (3)	0.58230 (7)	0.0281 (4)
H14	0.2109	−0.0866	0.5510	0.034*
C15	0.29934 (14)	0.1733 (3)	0.57106 (7)	0.0265 (3)
H15	0.3089	0.2115	0.5315	0.032*
C16	0.60272 (13)	1.1156 (2)	0.58024 (7)	0.0246 (3)
H16A	0.5719	1.2466	0.5940	0.029*
H16B	0.5658	1.0866	0.5411	0.029*
C17	0.72728 (13)	1.1438 (2)	0.57301 (7)	0.0222 (3)
C18	0.80536 (14)	0.9877 (3)	0.58319 (7)	0.0292 (4)
H18	0.7813	0.8574	0.5960	0.035*
C19	0.91849 (15)	1.0220 (3)	0.57456 (8)	0.0366 (4)
H19	0.9716	0.9148	0.5815	0.044*
C20	0.95450 (16)	1.2124 (3)	0.55586 (9)	0.0393 (5)
H20	1.0321	1.2363	0.5505	0.047*
C21	0.87698 (16)	1.3658 (3)	0.54511 (8)	0.0363 (4)
H21	0.9011	1.4954	0.5317	0.044*
C22	0.76351 (15)	1.3329 (3)	0.55370 (7)	0.0289 (4)
H22	0.7106	1.4401	0.5463	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0349 (2)	0.0300 (2)	0.0403 (3)	−0.00950 (18)	0.00055 (18)	0.00775 (18)
S1	0.0453 (3)	0.0251 (2)	0.0193 (2)	−0.01003 (18)	0.00228 (17)	0.00034 (15)
O1	0.0420 (7)	0.0318 (7)	0.0207 (6)	−0.0086 (5)	0.0057 (5)	−0.0001 (5)
N1	0.0222 (6)	0.0198 (7)	0.0206 (6)	−0.0004 (5)	0.0003 (5)	0.0027 (5)
C1	0.0217 (7)	0.0219 (8)	0.0236 (7)	0.0015 (6)	−0.0001 (6)	−0.0010 (6)
C2	0.0317 (8)	0.0307 (9)	0.0226 (8)	0.0000 (7)	0.0014 (6)	−0.0031 (7)
C3	0.0338 (9)	0.0389 (10)	0.0250 (8)	−0.0011 (8)	−0.0015 (7)	−0.0083 (7)
C4	0.0283 (9)	0.0328 (9)	0.0350 (9)	−0.0052 (7)	−0.0004 (7)	−0.0106 (8)
C5	0.0232 (8)	0.0251 (8)	0.0311 (8)	−0.0013 (6)	0.0031 (6)	−0.0029 (7)
C6	0.0171 (7)	0.0223 (8)	0.0237 (7)	0.0027 (6)	0.0000 (5)	−0.0017 (6)
C7	0.0217 (7)	0.0215 (8)	0.0222 (7)	0.0017 (6)	0.0011 (6)	0.0012 (6)
C8	0.0213 (7)	0.0198 (7)	0.0211 (7)	0.0023 (6)	0.0030 (5)	0.0006 (6)
C9	0.0239 (7)	0.0231 (8)	0.0194 (7)	0.0015 (6)	0.0028 (6)	−0.0007 (6)
C10	0.0201 (7)	0.0221 (8)	0.0235 (7)	0.0011 (6)	0.0044 (6)	−0.0003 (6)
C11	0.0317 (8)	0.0248 (8)	0.0234 (8)	−0.0040 (7)	0.0061 (6)	−0.0035 (6)
C12	0.0297 (8)	0.0274 (9)	0.0260 (8)	−0.0014 (7)	0.0076 (6)	0.0032 (6)
C13	0.0207 (7)	0.0219 (8)	0.0342 (9)	−0.0015 (6)	0.0042 (6)	0.0020 (6)
C14	0.0280 (8)	0.0295 (9)	0.0267 (8)	−0.0041 (7)	0.0000 (6)	−0.0023 (7)
C15	0.0285 (8)	0.0279 (9)	0.0233 (8)	−0.0026 (7)	0.0031 (6)	0.0009 (6)
C16	0.0233 (8)	0.0222 (8)	0.0279 (8)	0.0005 (6)	−0.0013 (6)	0.0065 (6)
C17	0.0244 (7)	0.0235 (8)	0.0186 (7)	−0.0005 (6)	0.0015 (5)	−0.0001 (6)
C18	0.0299 (8)	0.0289 (9)	0.0289 (8)	0.0026 (7)	0.0020 (7)	0.0057 (7)
C19	0.0284 (9)	0.0448 (11)	0.0367 (10)	0.0081 (8)	0.0032 (7)	0.0048 (8)
C20	0.0296 (9)	0.0526 (12)	0.0367 (10)	−0.0057 (9)	0.0114 (8)	−0.0020 (9)
C21	0.0409 (10)	0.0342 (10)	0.0354 (10)	−0.0091 (8)	0.0146 (8)	0.0004 (8)
C22	0.0354 (9)	0.0248 (8)	0.0272 (8)	−0.0006 (7)	0.0071 (7)	0.0006 (6)

Geometric parameters (Å, º) top

Cl1—C13	1.7383 (17)	C11—C12	1.394 (2)
S1—C8	1.7384 (15)	C11—H11	0.9500
S1—C1	1.7409 (16)	C12—C13	1.383 (2)
O1—C7	1.2256 (19)	C12—H12	0.9500
N1—C7	1.375 (2)	C13—C14	1.388 (2)
N1—C6	1.4189 (19)	C14—C15	1.382 (2)
N1—C16	1.4765 (19)	C14—H14	0.9500
C1—C2	1.398 (2)	C15—H15	0.9500
C1—C6	1.399 (2)	C16—C17	1.511 (2)
C2—C3	1.381 (3)	C16—H16A	0.9900
C2—H2	0.9500	C16—H16B	0.9900
C3—C4	1.385 (3)	C17—C22	1.389 (2)
C3—H3	0.9500	C17—C18	1.390 (2)
C4—C5	1.388 (3)	C18—C19	1.389 (2)
C4—H4	0.9500	C18—H18	0.9500
C5—C6	1.398 (2)	C19—C20	1.391 (3)
C5—H5	0.9500	C19—H19	0.9500
C7—C8	1.500 (2)	C20—C21	1.375 (3)
C8—C9	1.353 (2)	C20—H20	0.9500
C9—C10	1.459 (2)	C21—C22	1.391 (2)
C9—H9	0.9500	C21—H21	0.9500
C10—C11	1.404 (2)	C22—H22	0.9500
C10—C15	1.409 (2)

C8—S1—C1	103.94 (7)	C13—C12—C11	119.55 (15)
C7—N1—C6	126.48 (13)	C13—C12—H12	120.2
C7—N1—C16	115.70 (13)	C11—C12—H12	120.2
C6—N1—C16	117.77 (13)	C12—C13—C14	121.19 (15)
C2—C1—C6	120.57 (15)	C12—C13—Cl1	119.19 (13)
C2—C1—S1	114.98 (13)	C14—C13—Cl1	119.61 (13)
C6—C1—S1	124.44 (12)	C15—C14—C13	118.84 (16)
C3—C2—C1	120.39 (16)	C15—C14—H14	120.6
C3—C2—H2	119.8	C13—C14—H14	120.6
C1—C2—H2	119.8	C14—C15—C10	121.99 (15)
C2—C3—C4	119.67 (16)	C14—C15—H15	119.0
C2—C3—H3	120.2	C10—C15—H15	119.0
C4—C3—H3	120.2	N1—C16—C17	116.41 (13)
C3—C4—C5	120.20 (17)	N1—C16—H16A	108.2
C3—C4—H4	119.9	C17—C16—H16A	108.2
C5—C4—H4	119.9	N1—C16—H16B	108.2
C4—C5—C6	121.19 (16)	C17—C16—H16B	108.2
C4—C5—H5	119.4	H16A—C16—H16B	107.3
C6—C5—H5	119.4	C22—C17—C18	119.32 (15)
C5—C6—C1	117.97 (15)	C22—C17—C16	117.84 (14)
C5—C6—N1	120.27 (14)	C18—C17—C16	122.81 (15)
C1—C6—N1	121.75 (14)	C19—C18—C17	120.08 (17)
O1—C7—N1	119.88 (14)	C19—C18—H18	120.0
O1—C7—C8	119.37 (14)	C17—C18—H18	120.0
N1—C7—C8	120.74 (13)	C18—C19—C20	120.35 (17)
C9—C8—C7	115.58 (14)	C18—C19—H19	119.8
C9—C8—S1	122.72 (12)	C20—C19—H19	119.8
C7—C8—S1	121.71 (11)	C21—C20—C19	119.49 (17)
C8—C9—C10	132.25 (15)	C21—C20—H20	120.3
C8—C9—H9	113.9	C19—C20—H20	120.3
C10—C9—H9	113.9	C20—C21—C22	120.53 (17)
C11—C10—C15	117.47 (15)	C20—C21—H21	119.7
C11—C10—C9	125.75 (15)	C22—C21—H21	119.7
C15—C10—C9	116.71 (14)	C17—C22—C21	120.22 (17)
C12—C11—C10	120.96 (16)	C17—C22—H22	119.9
C12—C11—H11	119.5	C21—C22—H22	119.9
C10—C11—H11	119.5

C8—S1—C1—C2	−177.74 (12)	C7—C8—C9—C10	177.40 (15)
C8—S1—C1—C6	3.15 (15)	S1—C8—C9—C10	−2.8 (2)
C6—C1—C2—C3	0.9 (3)	C8—C9—C10—C11	−1.7 (3)
S1—C1—C2—C3	−178.23 (13)	C8—C9—C10—C15	−178.50 (16)
C1—C2—C3—C4	−0.4 (3)	C15—C10—C11—C12	−1.0 (2)
C2—C3—C4—C5	−0.4 (3)	C9—C10—C11—C12	−177.82 (15)
C3—C4—C5—C6	0.8 (3)	C10—C11—C12—C13	0.7 (3)
C4—C5—C6—C1	−0.3 (2)	C11—C12—C13—C14	0.2 (3)
C4—C5—C6—N1	−179.15 (15)	C11—C12—C13—Cl1	179.37 (13)
C2—C1—C6—C5	−0.6 (2)	C12—C13—C14—C15	−0.8 (3)
S1—C1—C6—C5	178.50 (12)	Cl1—C13—C14—C15	−179.96 (13)
C2—C1—C6—N1	178.28 (14)	C13—C14—C15—C10	0.5 (3)
S1—C1—C6—N1	−2.7 (2)	C11—C10—C15—C14	0.4 (2)
C7—N1—C6—C5	173.47 (15)	C9—C10—C15—C14	177.50 (15)
C16—N1—C6—C5	−9.2 (2)	C7—N1—C16—C17	−105.82 (16)
C7—N1—C6—C1	−5.4 (2)	C6—N1—C16—C17	76.60 (17)
C16—N1—C6—C1	171.94 (14)	N1—C16—C17—C22	−157.04 (15)
C6—N1—C7—O1	−169.28 (14)	N1—C16—C17—C18	24.9 (2)
C16—N1—C7—O1	13.4 (2)	C22—C17—C18—C19	0.6 (2)
C6—N1—C7—C8	11.9 (2)	C16—C17—C18—C19	178.62 (16)
C16—N1—C7—C8	−165.44 (13)	C17—C18—C19—C20	0.1 (3)
O1—C7—C8—C9	−9.2 (2)	C18—C19—C20—C21	−1.0 (3)
N1—C7—C8—C9	169.63 (14)	C19—C20—C21—C22	1.0 (3)
O1—C7—C8—S1	171.00 (12)	C18—C17—C22—C21	−0.5 (2)
N1—C7—C8—S1	−10.2 (2)	C16—C17—C22—C21	−178.64 (15)
C1—S1—C8—C9	−176.80 (13)	C20—C21—C22—C17	−0.3 (3)
C1—S1—C8—C7	2.99 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···O1ⁱ	0.99	2.43	3.271 (2)	142

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···O1ⁱ	0.99	2.43	3.271 (2)	142

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₆ClNOS
M_r	377.87
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	11.8931 (11), 6.5358 (6), 22.817 (2)
β (°)	93.239 (1)
V (Å³)	1770.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.33 × 0.18 × 0.13

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2016)
T_min, T_max	0.84, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	32976, 4771, 3718
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.132, 1.12
No. of reflections	4771
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.01, −0.47

Computer programs: APEX3 (Bruker, 2016), SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015), SHELXL2014 (Sheldrick, 2015a), PLATON (Spek, 2009), publCIF (Westrip, 2010).

Acknowledgements

The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

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