2-[4-tert-Butyl-5-(2-chloro­benz­yl)-1,3-thia­zol-2-yl]isoindoline-1,3-dione

Yao, Z.-G.; Peng, J.-M.; Huo, S.-F.; Hu, A.-X.

doi:10.1107/S1600536810042601

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2940

https://doi.org/10.1107/S1600536810042601

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2-[4-tert-Butyl-5-(2-chlorobenzyl)-1,3-thiazol-2-yl]isoindoline-1,3-dione

Zhi-Gang Yao,^a Jun-Mei Peng,^b Su-Fang Huo ^b and Ai-Xi Hu ^a ^*

^aSchool of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, People's Republic of China
^*Correspondence e-mail: axhu0731@yahoo.com.cn

(Received 18 October 2010; accepted 20 October 2010; online 23 October 2010)

In the title compound, C₂₂H₁₉ClN₂O₂S, the dihedral angle between the phenylene ring and the phthalimide ring system is 4.4 (1)°. There is no hydrogen bonding or π–π stacking in the crystal structure.

Related literature

For background to thiazole derivatives, see: Kazzouli et al. (2002 ); Holla et al. (2003 ); Hu et al. (2008 ), For background to phthalimide derivatives, see: Lima et al. (2002 ); Miyachi et al. (1997 ); Yachide et al. (2007 ).

Experimental

Crystal data

C₂₂H₁₉ClN₂O₂S
M_r = 410.90
Triclinic, $[P \overline 1]$
a = 7.8357 (4) Å
b = 8.1587 (4) Å
c = 16.1487 (8) Å
α = 100.404 (1)°
β = 95.897 (1)°
γ = 96.490 (1)°
V = 1000.85 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 173 K
0.46 × 0.30 × 0.28 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.868, T_max = 0.917
7798 measured reflections
3857 independent reflections
3268 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.122
S = 1.15
3857 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2003 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810042601/ng5049sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810042601/ng5049Isup2.hkl

checkCIF report

Comment top

Compounds containing thiazole ring have a wide spectrum of biological activities, many of them are well known as antiviral, antifungal agents (Kazzouli et al., 2002; Holla et al., 2003; Hu et al., 2008). N-substituted phthalimide derivatives are very important in pharmaceutical intermediates and drugs (Miyachi et al., 1997). Herein we report the synthesis and the crystal structure of the phthalimide compounds which contain the thiazole ring.

The molecular structure of the title compound, C₂₂H₁₉ClN₂O₂S, is shown in Fig 1. There are no hydrogen bonding and π–π stacking in the crystal structure. The van der Waals interactions maintain the structural cohesion.

Related literature top

For background to thiazole derivatives, see: Kazzouli et al. (2002); Holla et al. (2003); Hu et al. (2008), For background to phthalimide derivatives, see: Lima et al. (2002); Miyachi et al. (1997); Yachide et al. (2007).

Experimental top

A solution of 10 mmol 5-(2-chlorobenzyl)-4-tert-butylthiazol-2-amine and 10 mmol ph thalic anhydride in 15 ml acetic acid, then heated and refluxed for 23 h. After finishing the reaction, cooled the solution, and the precipitate formed, filtered, recrystallized with ethanol to give the title compound. The crystals for X-ray structure determination were obtained by slow evaporation of an ethanol solution at room temperature.

Structure description top

For background to thiazole derivatives, see: Kazzouli et al. (2002); Holla et al. (2003); Hu et al. (2008), For background to phthalimide derivatives, see: Lima et al. (2002); Miyachi et al. (1997); Yachide et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labelling scheme and 50% probability displacement ellipsoid (arbitrary spheres for H atoms).
	Fig. 2. A packing diagram for the title compound.

2-[4-tert-Butyl-5-(2-chlorobenzyl)-1,3-thiazol-2-yl]isoindoline-1,3-dione top

Crystal data top

C₂₂H₁₉ClN₂O₂S	Z = 2
M_r = 410.90	F(000) = 428
Triclinic, P1	D_x = 1.363 Mg m⁻³
Hall symbol: -P 1	Melting point: 425 K
a = 7.8357 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1587 (4) Å	Cell parameters from 5125 reflections
c = 16.1487 (8) Å	θ = 2.6–27.0°
α = 100.404 (1)°	µ = 0.32 mm⁻¹
β = 95.897 (1)°	T = 173 K
γ = 96.490 (1)°	Block, colorless
V = 1000.85 (9) Å³	0.46 × 0.30 × 0.28 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	3857 independent reflections
Radiation source: fine-focus sealed tube	3268 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ω scans	θ_max = 26.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
T_min = 0.868, T_max = 0.917	k = −10→10
7798 measured reflections	l = −19→19

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.0649P)² + 0.4002P] where P = (F_o² + 2F_c²)/3
3857 reflections	(Δ/σ)_max < 0.001
256 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₂H₁₉ClN₂O₂S	γ = 96.490 (1)°
M_r = 410.90	V = 1000.85 (9) Å³
Triclinic, P1	Z = 2
a = 7.8357 (4) Å	Mo Kα radiation
b = 8.1587 (4) Å	µ = 0.32 mm⁻¹
c = 16.1487 (8) Å	T = 173 K
α = 100.404 (1)°	0.46 × 0.30 × 0.28 mm
β = 95.897 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	3857 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3268 reflections with I > 2σ(I)
T_min = 0.868, T_max = 0.917	R_int = 0.018
7798 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.15	Δρ_max = 0.33 e Å⁻³
3857 reflections	Δρ_min = −0.31 e Å⁻³
256 parameters

Special details top

Experimental. The ¹HNMR(CDCl₃, 400 MHz) of the title compound were: 1.46(s,9H,3×CH₃), 4.41 (s, 2H, CH₂), 7.18~7.39 (m, 4H, C₆H₄), 7.79~7.96 (m, 4H, C₆H₄).And the yield was: 67.6%. m.p.423~427 K.

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
Cl1	−0.47492 (7)	−0.21014 (8)	0.32706 (3)	0.04128 (18)
S1	0.02664 (6)	0.03724 (6)	0.16354 (3)	0.02634 (15)
C1	0.2305 (2)	0.1497 (2)	0.18229 (12)	0.0236 (4)
C2	0.1795 (3)	0.1461 (2)	0.31377 (12)	0.0266 (4)
C3	0.0266 (2)	0.0574 (2)	0.27220 (12)	0.0239 (4)
C4	0.2332 (3)	0.1918 (3)	0.40993 (13)	0.0366 (5)
C5	0.4226 (4)	0.2725 (4)	0.42868 (16)	0.0624 (9)
H5A	0.4953	0.1967	0.3993	0.094*
H5B	0.4592	0.2932	0.4900	0.094*
H5C	0.4347	0.3793	0.4088	0.094*
C6	0.2175 (3)	0.0330 (3)	0.44847 (14)	0.0389 (5)
H6A	0.0978	−0.0232	0.4360	0.058*
H6B	0.2495	0.0640	0.5101	0.058*
H6C	0.2950	−0.0434	0.4240	0.058*
C7	0.1182 (4)	0.3151 (3)	0.45113 (15)	0.0555 (7)
H7A	0.1307	0.4177	0.4275	0.083*
H7B	0.1534	0.3433	0.5126	0.083*
H7C	−0.0029	0.2630	0.4396	0.083*
C8	−0.1313 (2)	−0.0235 (2)	0.30286 (12)	0.0261 (4)
H8A	−0.2359	0.0057	0.2720	0.031*
H8B	−0.1298	0.0241	0.3639	0.031*
C9	−0.1445 (2)	−0.2135 (2)	0.29113 (12)	0.0255 (4)
C10	−0.2985 (3)	−0.3103 (3)	0.29935 (12)	0.0298 (4)
C11	−0.3166 (3)	−0.4842 (3)	0.28567 (15)	0.0422 (6)
H11	−0.4235	−0.5467	0.2909	0.051*
C12	−0.1785 (4)	−0.5656 (3)	0.26456 (18)	0.0510 (7)
H12	−0.1901	−0.6849	0.2547	0.061*
C13	−0.0231 (3)	−0.4749 (3)	0.25766 (18)	0.0492 (6)
H13	0.0730	−0.5313	0.2441	0.059*
C14	−0.0074 (3)	−0.3009 (3)	0.27052 (15)	0.0349 (5)
H14	0.1001	−0.2396	0.2651	0.042*
C15	0.4999 (2)	0.1549 (2)	0.11270 (12)	0.0248 (4)
C16	0.5493 (2)	0.2158 (2)	0.03643 (12)	0.0245 (4)
C17	0.7093 (3)	0.2341 (3)	0.00803 (14)	0.0306 (4)
H17	0.8079	0.2015	0.0369	0.037*
C18	0.7203 (3)	0.3020 (3)	−0.06437 (13)	0.0319 (5)
H18	0.8292	0.3190	−0.0847	0.038*
C19	0.5758 (3)	0.3453 (3)	−0.10749 (13)	0.0307 (4)
H19	0.5873	0.3896	−0.1574	0.037*
C20	0.4131 (2)	0.3257 (3)	−0.07953 (12)	0.0270 (4)
H20	0.3135	0.3546	−0.1094	0.032*
C21	0.4048 (2)	0.2618 (2)	−0.00597 (11)	0.0228 (4)
C22	0.2572 (2)	0.2381 (2)	0.04291 (12)	0.0249 (4)
N1	0.2936 (2)	0.2002 (2)	0.26111 (10)	0.0276 (4)
N2	0.3239 (2)	0.1807 (2)	0.11564 (10)	0.0244 (3)
O1	0.58277 (18)	0.09357 (19)	0.16259 (9)	0.0334 (3)
O2	0.10930 (18)	0.2615 (2)	0.02800 (9)	0.0374 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0275 (3)	0.0591 (4)	0.0341 (3)	−0.0019 (2)	0.0104 (2)	0.0021 (2)
S1	0.0230 (3)	0.0335 (3)	0.0218 (3)	−0.00074 (19)	0.00394 (18)	0.00557 (19)
C1	0.0242 (9)	0.0245 (9)	0.0229 (9)	0.0027 (7)	0.0047 (7)	0.0062 (7)
C2	0.0319 (10)	0.0250 (10)	0.0225 (10)	0.0002 (8)	0.0058 (8)	0.0043 (7)
C3	0.0285 (10)	0.0230 (9)	0.0224 (9)	0.0048 (7)	0.0070 (8)	0.0071 (7)
C4	0.0447 (13)	0.0408 (12)	0.0211 (10)	−0.0054 (10)	0.0049 (9)	0.0044 (9)
C5	0.0642 (18)	0.083 (2)	0.0264 (12)	−0.0353 (15)	−0.0045 (12)	0.0075 (12)
C6	0.0412 (13)	0.0510 (14)	0.0266 (11)	0.0052 (10)	0.0068 (9)	0.0125 (10)
C7	0.092 (2)	0.0431 (14)	0.0298 (12)	0.0145 (14)	0.0097 (13)	−0.0021 (10)
C8	0.0262 (10)	0.0280 (10)	0.0266 (10)	0.0047 (8)	0.0073 (8)	0.0086 (8)
C9	0.0261 (10)	0.0284 (10)	0.0225 (9)	0.0018 (8)	0.0003 (7)	0.0093 (8)
C10	0.0302 (10)	0.0370 (11)	0.0217 (9)	−0.0027 (8)	0.0026 (8)	0.0090 (8)
C11	0.0456 (13)	0.0381 (13)	0.0398 (13)	−0.0132 (10)	−0.0033 (10)	0.0154 (10)
C12	0.0573 (16)	0.0255 (11)	0.0673 (17)	−0.0004 (11)	−0.0070 (13)	0.0134 (11)
C13	0.0443 (14)	0.0326 (12)	0.0706 (18)	0.0120 (10)	−0.0009 (12)	0.0105 (12)
C14	0.0297 (11)	0.0294 (11)	0.0465 (13)	0.0037 (8)	0.0038 (9)	0.0105 (9)
C15	0.0214 (9)	0.0261 (10)	0.0266 (10)	0.0022 (7)	0.0031 (7)	0.0050 (8)
C16	0.0234 (9)	0.0258 (10)	0.0242 (9)	0.0023 (7)	0.0047 (7)	0.0044 (8)
C17	0.0198 (9)	0.0369 (11)	0.0366 (11)	0.0055 (8)	0.0064 (8)	0.0086 (9)
C18	0.0247 (10)	0.0372 (11)	0.0350 (11)	0.0021 (8)	0.0135 (9)	0.0060 (9)
C19	0.0345 (11)	0.0343 (11)	0.0227 (10)	−0.0003 (8)	0.0078 (8)	0.0045 (8)
C20	0.0244 (10)	0.0340 (11)	0.0227 (9)	0.0033 (8)	0.0019 (8)	0.0062 (8)
C21	0.0197 (9)	0.0260 (10)	0.0213 (9)	0.0006 (7)	0.0036 (7)	0.0023 (7)
C22	0.0232 (10)	0.0290 (10)	0.0227 (9)	0.0022 (7)	0.0016 (7)	0.0068 (8)
N1	0.0315 (9)	0.0268 (8)	0.0237 (8)	−0.0020 (7)	0.0060 (7)	0.0052 (7)
N2	0.0205 (8)	0.0309 (9)	0.0236 (8)	0.0034 (6)	0.0039 (6)	0.0093 (6)
O1	0.0284 (7)	0.0411 (8)	0.0343 (8)	0.0081 (6)	0.0003 (6)	0.0166 (7)
O2	0.0208 (7)	0.0607 (10)	0.0362 (8)	0.0081 (7)	0.0049 (6)	0.0216 (7)

Geometric parameters (Å, º) top

Cl1—C10	1.741 (2)	C9—C10	1.397 (3)
S1—C1	1.7188 (19)	C10—C11	1.385 (3)
S1—C3	1.7327 (19)	C11—C12	1.373 (4)
C1—N1	1.292 (2)	C11—H11	0.9500
C1—N2	1.406 (2)	C12—C13	1.377 (4)
C2—C3	1.369 (3)	C12—H12	0.9500
C2—N1	1.385 (2)	C13—C14	1.386 (3)
C2—C4	1.532 (3)	C13—H13	0.9500
C3—C8	1.507 (3)	C14—H14	0.9500
C4—C5	1.531 (3)	C15—O1	1.197 (2)
C4—C6	1.534 (3)	C15—N2	1.422 (2)
C4—C7	1.534 (3)	C15—C16	1.480 (3)
C5—H5A	0.9800	C16—C17	1.380 (3)
C5—H5B	0.9800	C16—C21	1.386 (3)
C5—H5C	0.9800	C17—C18	1.388 (3)
C6—H6A	0.9800	C17—H17	0.9500
C6—H6B	0.9800	C18—C19	1.382 (3)
C6—H6C	0.9800	C18—H18	0.9500
C7—H7A	0.9800	C19—C20	1.398 (3)
C7—H7B	0.9800	C19—H19	0.9500
C7—H7C	0.9800	C20—C21	1.385 (3)
C8—C9	1.518 (3)	C20—H20	0.9500
C8—H8A	0.9900	C21—C22	1.480 (3)
C8—H8B	0.9900	C22—O2	1.203 (2)
C9—C14	1.391 (3)	C22—N2	1.414 (2)

C1—S1—C3	88.77 (9)	C11—C10—C9	122.3 (2)
N1—C1—N2	122.33 (17)	C11—C10—Cl1	118.45 (17)
N1—C1—S1	115.89 (14)	C9—C10—Cl1	119.27 (16)
N2—C1—S1	121.76 (14)	C12—C11—C10	119.4 (2)
C3—C2—N1	114.54 (17)	C12—C11—H11	120.3
C3—C2—C4	127.00 (18)	C10—C11—H11	120.3
N1—C2—C4	118.45 (17)	C11—C12—C13	120.3 (2)
C2—C3—C8	132.65 (17)	C11—C12—H12	119.9
C2—C3—S1	109.93 (14)	C13—C12—H12	119.9
C8—C3—S1	117.41 (14)	C12—C13—C14	119.8 (2)
C5—C4—C2	109.70 (17)	C12—C13—H13	120.1
C5—C4—C6	107.7 (2)	C14—C13—H13	120.1
C2—C4—C6	110.24 (18)	C13—C14—C9	121.9 (2)
C5—C4—C7	109.5 (2)	C13—C14—H14	119.1
C2—C4—C7	110.09 (19)	C9—C14—H14	119.1
C6—C4—C7	109.56 (19)	O1—C15—N2	124.78 (18)
C4—C5—H5A	109.5	O1—C15—C16	129.95 (18)
C4—C5—H5B	109.5	N2—C15—C16	105.26 (15)
H5A—C5—H5B	109.5	C17—C16—C21	121.50 (18)
C4—C5—H5C	109.5	C17—C16—C15	129.50 (18)
H5A—C5—H5C	109.5	C21—C16—C15	108.97 (16)
H5B—C5—H5C	109.5	C16—C17—C18	117.32 (18)
C4—C6—H6A	109.5	C16—C17—H17	121.3
C4—C6—H6B	109.5	C18—C17—H17	121.3
H6A—C6—H6B	109.5	C19—C18—C17	121.24 (18)
C4—C6—H6C	109.5	C19—C18—H18	119.4
H6A—C6—H6C	109.5	C17—C18—H18	119.4
H6B—C6—H6C	109.5	C18—C19—C20	121.71 (19)
C4—C7—H7A	109.5	C18—C19—H19	119.1
C4—C7—H7B	109.5	C20—C19—H19	119.1
H7A—C7—H7B	109.5	C21—C20—C19	116.44 (18)
C4—C7—H7C	109.5	C21—C20—H20	121.8
H7A—C7—H7C	109.5	C19—C20—H20	121.8
H7B—C7—H7C	109.5	C20—C21—C16	121.75 (17)
C3—C8—C9	113.97 (16)	C20—C21—C22	129.59 (17)
C3—C8—H8A	108.8	C16—C21—C22	108.59 (16)
C9—C8—H8A	108.8	O2—C22—N2	124.31 (18)
C3—C8—H8B	108.8	O2—C22—C21	129.93 (18)
C9—C8—H8B	108.8	N2—C22—C21	105.75 (15)
H8A—C8—H8B	107.7	C1—N1—C2	110.85 (16)
C14—C9—C10	116.45 (19)	C1—N2—C22	125.37 (16)
C14—C9—C8	122.59 (17)	C1—N2—C15	123.47 (15)
C10—C9—C8	120.96 (18)	C22—N2—C15	111.15 (15)

C3—S1—C1—N1	−0.76 (16)	N2—C15—C16—C21	−4.5 (2)
C3—S1—C1—N2	177.63 (16)	C21—C16—C17—C18	0.6 (3)
N1—C2—C3—C8	−179.96 (18)	C15—C16—C17—C18	−177.14 (19)
C4—C2—C3—C8	−0.9 (4)	C16—C17—C18—C19	−1.7 (3)
N1—C2—C3—S1	1.1 (2)	C17—C18—C19—C20	1.1 (3)
C4—C2—C3—S1	−179.79 (17)	C18—C19—C20—C21	0.5 (3)
C1—S1—C3—C2	−0.25 (15)	C19—C20—C21—C16	−1.6 (3)
C1—S1—C3—C8	−179.33 (15)	C19—C20—C21—C22	175.01 (18)
C3—C2—C4—C5	173.1 (2)	C17—C16—C21—C20	1.1 (3)
N1—C2—C4—C5	−7.9 (3)	C15—C16—C21—C20	179.23 (17)
C3—C2—C4—C6	54.6 (3)	C17—C16—C21—C22	−176.19 (18)
N1—C2—C4—C6	−126.4 (2)	C15—C16—C21—C22	2.0 (2)
C3—C2—C4—C7	−66.4 (3)	C20—C21—C22—O2	3.8 (4)
N1—C2—C4—C7	112.6 (2)	C16—C21—C22—O2	−179.2 (2)
C2—C3—C8—C9	−104.1 (2)	C20—C21—C22—N2	−175.65 (19)
S1—C3—C8—C9	74.74 (19)	C16—C21—C22—N2	1.3 (2)
C3—C8—C9—C14	12.5 (3)	N2—C1—N1—C2	−176.86 (17)
C3—C8—C9—C10	−166.43 (18)	S1—C1—N1—C2	1.5 (2)
C14—C9—C10—C11	−1.7 (3)	C3—C2—N1—C1	−1.7 (2)
C8—C9—C10—C11	177.34 (19)	C4—C2—N1—C1	179.14 (18)
C14—C9—C10—Cl1	178.77 (15)	N1—C1—N2—C22	−134.9 (2)
C8—C9—C10—Cl1	−2.2 (3)	S1—C1—N2—C22	46.8 (2)
C9—C10—C11—C12	1.0 (3)	N1—C1—N2—C15	46.1 (3)
Cl1—C10—C11—C12	−179.38 (19)	S1—C1—N2—C15	−132.20 (17)
C10—C11—C12—C13	0.5 (4)	O2—C22—N2—C1	−2.9 (3)
C11—C12—C13—C14	−1.2 (4)	C21—C22—N2—C1	176.62 (16)
C12—C13—C14—C9	0.6 (4)	O2—C22—N2—C15	176.22 (19)
C10—C9—C14—C13	0.8 (3)	C21—C22—N2—C15	−4.3 (2)
C8—C9—C14—C13	−178.1 (2)	O1—C15—N2—C1	5.6 (3)
O1—C15—C16—C17	−7.7 (4)	C16—C15—N2—C1	−175.46 (16)
N2—C15—C16—C17	173.5 (2)	O1—C15—N2—C22	−173.47 (19)
O1—C15—C16—C21	174.3 (2)	C16—C15—N2—C22	5.4 (2)

Experimental details

Crystal data
Chemical formula	C₂₂H₁₉ClN₂O₂S
M_r	410.90
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.8357 (4), 8.1587 (4), 16.1487 (8)
α, β, γ (°)	100.404 (1), 95.897 (1), 96.490 (1)
V (Å³)	1000.85 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.46 × 0.30 × 0.28

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.868, 0.917
No. of measured, independent and observed [I > 2σ(I)] reflections	7798, 3857, 3268
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.122, 1.15
No. of reflections	3857
No. of parameters	256
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.31

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

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