(E)-2-{[4-tert-Butyl-5-(2,4-dichloro­benz­yl)thia­zol-2-yl]imino­meth­yl}phenol

Hu, A.-X.; Cao, G.; Mang, Y.-Q.

doi:10.1107/S1600536807059600

(E)-2-{[4-tert-Butyl-5-(2,4-dichlorobenzyl)thiazol-2-yl]iminomethyl}phenol

Geometric parameters of the title compound, C₂₁H₂₀Cl₂N₂OS, a Schiff base, are in the usual ranges. The 4-hydroxyphenyl group and thiazole ring are almost coplanar, with a dihedral angle of 2.4 (1)°; the 2,4-dichlorobenzyl group is approximately perpendicular to the thiazole ring [dihedral angle = 86.6 (2)°]. The molecular conformation is stabilized by an intramolecular O—H

N hydrogen bond.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059600/bt2623sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059600/bt2623Isup2.hkl Contains datablock I

CCDC reference: 673018

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R factor = 0.041
wR factor = 0.110
Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.94 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.61 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11    -   C13     ..       5.13 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

In recent years, there has been considerable and increasing interest in the study of Schiff-base containing thiazole rings due to their antiviral, anticancer and antibacterial activities (Hu et al., 2006). Herein we report the synthesis and crystal structure of (E)-2-((4-tert-butyl-5-(2,4-dichlorobenzyl)thiazol-2- ylimino)methyl)phenol.

A perspective view of the title compound with the labeling scheme is shown in Fig. 1 with dashed line indicateing the hydrogen bond forming a six-membered ring. The length of C=N double bond is 1.286 (2) Å. The 2,4-dichlorobenzyl is approximately perpendicular to the thiazole ring with a dihedral angle of 86.6 (2)°.

Related literature top

For related literature, see: Hu et al. (2006).

Experimental top

A solution of thiourea (0.03 mol) and 2-bromo-1-(2,4-dichlorophenyl)-4,4-dimethylpentan-3-one (0.03 mol) in ethanol (70 ml) was refluxed for 9 h (monitoring by TLC). A part of the solvent was evaporated, and the precipitate formed was filtered out, dried, giving a yellowish crystalline substance which was the hydrobromide. The salt dissolved directly in ethanol and was neutralized with ammonia. The precipitate was filtered out and washed with water, dried to give 4-tert-butyl-5- (2,4-dichlorobenzyl)thiazol-2-amine. Then 1 mmol salicylal was dissolved in 5 ml of freshly dried alcohol and heated to 348 K, and the above-prepared alcohol solution of 4-tert-butyl-5-(2,4-dichlorobenzyl)thiazol-2-amine(1 mmol) was added dropwise and the resulting raction mixture was stirred at this temperature for furture 8.5 h. The mixture was then cooled, and the yellow solid was removed by filtration and recrystallized from dried alcohol to give the desired product. Yield: 75.1%. m.p. 417–418 K. Spectroscopic analysis: ¹H-NMR (CDCl₃, 400 MHz) (p.p.m.): 1.43(s, 9H, (CH₃)₃), 4.33(s, 2H, CH₂), 6.95(dd, J = 8.0 Hz, J = 8.0 Hz, 1H, 2-HOC₆H₄5-H), 7.00(d, J = 8.0 Hz, 1H, 2-HOC₆H₄3-H), 7.09(d, J = 8.0 Hz, 1H, 2,4-Cl₂C₆H₃6-H), 7.21(dd, J = 8.0 Hz, J =1.6 Hz, 1H, 2,4-Cl₂C₆H₃5-H), 7.40(ddd, J = 8.0 Hz, J = 8.0 Hz, J = 1.6 Hz,1H, 2-HOC₆H₄4-H), 7.43(d, J = 1.6 Hz, 1H, 2,4-Cl₂C₆H₃3-H), 7.44(dd, J = 8.0 Hz, J = 1.6 Hz,1H, 2-HOC₆H₄6-H), 9.06(s, 1H, N=CH), 12.28(s, 1H, OH). Crystals suitable for X-ray structure determination were obtained by slow evaporation of an ethanol solution at room temperature.

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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2005); software used to prepare material for publication: SHELXTL (Bruker, 2005).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms. the hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of the title compound, with all H atoms omitted for clarity.

(E)-2-{[(4-tert-Butyl-5-(2,4-dichlorobenzyl)thiazol-2-yl]iminomethyl}phenol top

Crystal data top

C₂₁H₂₀Cl₂N₂OS	F(000) = 872
M_r = 419.35	D_x = 1.376 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5068 reflections
a = 8.3005 (4) Å	θ = 2.6–27.0°
b = 19.0883 (10) Å	µ = 0.44 mm⁻¹
c = 13.3014 (7) Å	T = 173 K
β = 106.121 (1)°	Block, yellow
V = 2024.63 (18) Å³	0.48 × 0.38 × 0.33 mm
Z = 4

Data collection top

Bruker AXS SMART 1000 CCD diffractometer	4441 independent reflections
Radiation source: fine-focus sealed tube	3382 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 27.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→10
T_min = 0.818, T_max = 0.869	k = −20→24
11999 measured reflections	l = −16→17

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) = 0.110	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.051P)² + 0.8438P] where P = (F_o² + 2F_c²)/3
4441 reflections	(Δ/σ)_max = 0.001
248 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₁H₂₀Cl₂N₂OS	V = 2024.63 (18) Å³
M_r = 419.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.3005 (4) Å	µ = 0.44 mm⁻¹
b = 19.0883 (10) Å	T = 173 K
c = 13.3014 (7) Å	0.48 × 0.38 × 0.33 mm
β = 106.121 (1)°

Data collection top

Bruker AXS SMART 1000 CCD diffractometer	4441 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3382 reflections with I > 2σ(I)
T_min = 0.818, T_max = 0.869	R_int = 0.027
11999 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.05	Δρ_max = 0.39 e Å⁻³
4441 reflections	Δρ_min = −0.24 e Å⁻³
248 parameters

Special details top

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	0.03027 (7)	0.47395 (3)	0.30136 (6)	0.0597 (2)
Cl2	0.64380 (8)	0.36001 (4)	0.37832 (4)	0.05161 (18)
S1	0.48133 (6)	0.25450 (2)	0.58721 (4)	0.02904 (13)
C1	0.5844 (2)	0.17648 (9)	0.62257 (14)	0.0254 (4)
C2	0.7997 (2)	0.24959 (10)	0.65619 (14)	0.0261 (4)
C3	0.6734 (2)	0.29737 (10)	0.62080 (14)	0.0258 (4)
C4	0.5664 (2)	0.05644 (10)	0.63223 (14)	0.0262 (4)
H4	0.6855	0.0563	0.6557	0.031*
C5	0.4777 (2)	−0.00926 (10)	0.62176 (14)	0.0265 (4)
C6	0.3014 (2)	−0.01282 (10)	0.58307 (16)	0.0309 (4)
C7	0.2203 (3)	−0.07746 (11)	0.57246 (17)	0.0377 (5)
H7	0.1016	−0.0799	0.5463	0.045*
C8	0.3135 (3)	−0.13780 (11)	0.60019 (16)	0.0365 (5)
H8	0.2577	−0.1818	0.5930	0.044*
C9	0.4859 (3)	−0.13567 (11)	0.63817 (16)	0.0350 (5)
H9	0.5480	−0.1778	0.6571	0.042*
C10	0.5676 (2)	−0.07210 (10)	0.64841 (15)	0.0306 (4)
H10	0.6864	−0.0707	0.6738	0.037*
C11	0.9897 (2)	0.25934 (11)	0.69580 (17)	0.0346 (5)
C12	1.0421 (3)	0.24370 (16)	0.8141 (2)	0.0601 (7)
H12A	1.1647	0.2416	0.8397	0.090*
H12B	0.9947	0.1986	0.8269	0.090*
H12C	1.0003	0.2809	0.8511	0.090*
C13	1.0742 (3)	0.20476 (14)	0.6436 (2)	0.0515 (6)
H13A	1.0452	0.2137	0.5681	0.077*
H13B	1.0355	0.1579	0.6560	0.077*
H13C	1.1961	0.2076	0.6731	0.077*
C14	1.0498 (3)	0.33084 (14)	0.6732 (3)	0.0745 (10)
H14A	1.1727	0.3315	0.6932	0.112*
H14B	1.0091	0.3664	0.7134	0.112*
H14C	1.0066	0.3410	0.5983	0.112*
C15	0.6701 (2)	0.37653 (10)	0.61058 (15)	0.0294 (4)
H15A	0.6787	0.3977	0.6798	0.035*
H15B	0.7686	0.3920	0.5881	0.035*
C16	0.5124 (2)	0.40248 (9)	0.53298 (14)	0.0267 (4)
C17	0.4866 (2)	0.39610 (10)	0.42552 (15)	0.0298 (4)
C18	0.3403 (3)	0.41804 (11)	0.35340 (17)	0.0353 (5)
H18	0.3262	0.4134	0.2803	0.042*
C19	0.2158 (2)	0.44676 (10)	0.39103 (18)	0.0367 (5)
C20	0.2354 (3)	0.45450 (11)	0.49643 (19)	0.0393 (5)
H20	0.1488	0.4747	0.5210	0.047*
C21	0.3834 (3)	0.43247 (10)	0.56634 (17)	0.0341 (5)
H21	0.3973	0.4380	0.6392	0.041*
N1	0.74610 (19)	0.18098 (8)	0.65692 (12)	0.0270 (3)
N2	0.48872 (19)	0.11518 (8)	0.61060 (12)	0.0267 (3)
O1	0.20766 (18)	0.04525 (8)	0.55414 (14)	0.0452 (4)
H1	0.2704	0.0806	0.5635	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0377 (3)	0.0436 (3)	0.0777 (5)	0.0068 (2)	−0.0176 (3)	−0.0032 (3)
Cl2	0.0522 (4)	0.0697 (4)	0.0373 (3)	0.0217 (3)	0.0197 (3)	0.0039 (3)
S1	0.0232 (2)	0.0250 (2)	0.0365 (3)	−0.00092 (18)	0.00423 (19)	0.0030 (2)
C1	0.0287 (10)	0.0234 (9)	0.0241 (9)	−0.0013 (7)	0.0073 (8)	0.0007 (7)
C2	0.0258 (9)	0.0246 (9)	0.0273 (9)	−0.0024 (7)	0.0062 (7)	0.0000 (8)
C3	0.0243 (9)	0.0249 (9)	0.0265 (9)	−0.0041 (7)	0.0044 (7)	0.0014 (7)
C4	0.0253 (9)	0.0280 (10)	0.0249 (9)	−0.0030 (7)	0.0060 (8)	0.0005 (8)
C5	0.0300 (10)	0.0261 (10)	0.0227 (9)	−0.0014 (7)	0.0063 (8)	−0.0001 (7)
C6	0.0290 (10)	0.0280 (10)	0.0343 (11)	−0.0027 (8)	0.0066 (8)	−0.0019 (8)
C7	0.0295 (11)	0.0358 (12)	0.0463 (12)	−0.0099 (9)	0.0081 (9)	−0.0037 (10)
C8	0.0458 (12)	0.0267 (10)	0.0385 (11)	−0.0121 (9)	0.0143 (10)	−0.0028 (9)
C9	0.0468 (13)	0.0247 (10)	0.0321 (11)	0.0003 (9)	0.0090 (9)	0.0022 (8)
C10	0.0301 (10)	0.0292 (10)	0.0306 (10)	−0.0007 (8)	0.0054 (8)	0.0014 (8)
C11	0.0229 (9)	0.0325 (11)	0.0445 (12)	−0.0022 (8)	0.0024 (9)	0.0002 (9)
C12	0.0365 (13)	0.087 (2)	0.0478 (15)	0.0051 (13)	−0.0041 (11)	−0.0078 (14)
C13	0.0311 (12)	0.0542 (15)	0.0726 (17)	−0.0014 (10)	0.0200 (12)	−0.0005 (13)
C14	0.0275 (12)	0.0427 (15)	0.139 (3)	−0.0083 (10)	−0.0015 (15)	0.0170 (17)
C15	0.0311 (10)	0.0249 (10)	0.0300 (10)	−0.0023 (8)	0.0047 (8)	0.0006 (8)
C16	0.0299 (10)	0.0206 (9)	0.0291 (10)	−0.0025 (7)	0.0072 (8)	0.0037 (8)
C17	0.0323 (10)	0.0249 (10)	0.0329 (10)	0.0020 (8)	0.0098 (9)	0.0025 (8)
C18	0.0385 (12)	0.0299 (11)	0.0333 (11)	−0.0010 (9)	0.0032 (9)	0.0000 (9)
C19	0.0277 (10)	0.0232 (10)	0.0504 (13)	−0.0009 (8)	−0.0037 (9)	0.0032 (9)
C20	0.0308 (11)	0.0320 (11)	0.0564 (14)	0.0034 (9)	0.0143 (10)	0.0001 (10)
C21	0.0390 (12)	0.0288 (10)	0.0366 (11)	0.0017 (8)	0.0141 (9)	0.0009 (8)
N1	0.0259 (8)	0.0240 (8)	0.0301 (8)	−0.0020 (6)	0.0059 (7)	0.0009 (6)
N2	0.0262 (8)	0.0240 (8)	0.0289 (8)	−0.0035 (6)	0.0060 (7)	0.0010 (6)
O1	0.0271 (8)	0.0296 (8)	0.0722 (11)	−0.0007 (6)	0.0024 (7)	0.0017 (8)

Geometric parameters (Å, º) top

Cl1—C19	1.745 (2)	C11—C13	1.527 (3)
Cl2—C17	1.740 (2)	C11—C12	1.541 (3)
S1—C1	1.7168 (19)	C12—H12A	0.9800
S1—C3	1.7367 (18)	C12—H12B	0.9800
C1—N1	1.295 (2)	C12—H12C	0.9800
C1—N2	1.398 (2)	C13—H13A	0.9800
C2—C3	1.370 (3)	C13—H13B	0.9800
C2—N1	1.384 (2)	C13—H13C	0.9800
C2—C11	1.529 (3)	C14—H14A	0.9800
C3—C15	1.517 (3)	C14—H14B	0.9800
C4—N2	1.286 (2)	C14—H14C	0.9800
C4—C5	1.442 (3)	C15—C16	1.507 (3)
C4—H4	0.9500	C15—H15A	0.9900
C5—C10	1.405 (3)	C15—H15B	0.9900
C5—C6	1.411 (3)	C16—C17	1.391 (3)
C6—O1	1.348 (2)	C16—C21	1.391 (3)
C6—C7	1.394 (3)	C17—C18	1.387 (3)
C7—C8	1.379 (3)	C18—C19	1.381 (3)
C7—H7	0.9500	C18—H18	0.9500
C8—C9	1.380 (3)	C19—C20	1.374 (3)
C8—H8	0.9500	C20—C21	1.384 (3)
C9—C10	1.378 (3)	C20—H20	0.9500
C9—H9	0.9500	C21—H21	0.9500
C10—H10	0.9500	O1—H1	0.8400
C11—C14	1.512 (3)

C1—S1—C3	89.22 (9)	H12A—C12—H12C	109.5
N1—C1—N2	126.57 (17)	H12B—C12—H12C	109.5
N1—C1—S1	115.33 (14)	C11—C13—H13A	109.5
N2—C1—S1	118.10 (13)	C11—C13—H13B	109.5
C3—C2—N1	114.54 (16)	H13A—C13—H13B	109.5
C3—C2—C11	130.90 (17)	C11—C13—H13C	109.5
N1—C2—C11	114.57 (16)	H13A—C13—H13C	109.5
C2—C3—C15	133.40 (17)	H13B—C13—H13C	109.5
C2—C3—S1	109.57 (14)	C11—C14—H14A	109.5
C15—C3—S1	116.97 (14)	C11—C14—H14B	109.5
N2—C4—C5	121.73 (17)	H14A—C14—H14B	109.5
N2—C4—H4	119.1	C11—C14—H14C	109.5
C5—C4—H4	119.1	H14A—C14—H14C	109.5
C10—C5—C6	118.38 (17)	H14B—C14—H14C	109.5
C10—C5—C4	119.79 (17)	C16—C15—C3	112.31 (16)
C6—C5—C4	121.82 (17)	C16—C15—H15A	109.1
O1—C6—C7	118.32 (18)	C3—C15—H15A	109.1
O1—C6—C5	121.51 (17)	C16—C15—H15B	109.1
C7—C6—C5	120.16 (19)	C3—C15—H15B	109.1
C8—C7—C6	119.5 (2)	H15A—C15—H15B	107.9
C8—C7—H7	120.2	C17—C16—C21	116.82 (18)
C6—C7—H7	120.2	C17—C16—C15	122.14 (17)
C7—C8—C9	121.40 (19)	C21—C16—C15	121.02 (18)
C7—C8—H8	119.3	C18—C17—C16	122.69 (18)
C9—C8—H8	119.3	C18—C17—Cl2	118.06 (16)
C10—C9—C8	119.60 (19)	C16—C17—Cl2	119.24 (15)
C10—C9—H9	120.2	C19—C18—C17	117.96 (19)
C8—C9—H9	120.2	C19—C18—H18	121.0
C9—C10—C5	120.95 (19)	C17—C18—H18	121.0
C9—C10—H10	119.5	C20—C19—C18	121.62 (19)
C5—C10—H10	119.5	C20—C19—Cl1	119.84 (17)
C14—C11—C13	107.9 (2)	C18—C19—Cl1	118.54 (17)
C14—C11—C2	114.02 (17)	C19—C20—C21	119.0 (2)
C13—C11—C2	108.69 (17)	C19—C20—H20	120.5
C14—C11—C12	111.3 (2)	C21—C20—H20	120.5
C13—C11—C12	107.29 (19)	C20—C21—C16	121.9 (2)
C2—C11—C12	107.46 (17)	C20—C21—H21	119.0
C11—C12—H12A	109.5	C16—C21—H21	119.0
C11—C12—H12B	109.5	C1—N1—C2	111.35 (15)
H12A—C12—H12B	109.5	C4—N2—C1	118.08 (16)
C11—C12—H12C	109.5	C6—O1—H1	109.5

C3—S1—C1—N1	0.42 (15)	N1—C2—C11—C12	−68.7 (2)
C3—S1—C1—N2	−178.71 (15)	C2—C3—C15—C16	159.3 (2)
N1—C2—C3—C15	176.90 (19)	S1—C3—C15—C16	−23.9 (2)
C11—C2—C3—C15	−2.5 (4)	C3—C15—C16—C17	−75.0 (2)
N1—C2—C3—S1	−0.1 (2)	C3—C15—C16—C21	103.3 (2)
C11—C2—C3—S1	−179.56 (17)	C21—C16—C17—C18	−0.1 (3)
C1—S1—C3—C2	−0.15 (14)	C15—C16—C17—C18	178.22 (18)
C1—S1—C3—C15	−177.72 (15)	C21—C16—C17—Cl2	179.24 (15)
N2—C4—C5—C10	−178.66 (18)	C15—C16—C17—Cl2	−2.4 (3)
N2—C4—C5—C6	2.7 (3)	C16—C17—C18—C19	−0.5 (3)
C10—C5—C6—O1	−178.73 (19)	Cl2—C17—C18—C19	−179.90 (16)
C4—C5—C6—O1	−0.1 (3)	C17—C18—C19—C20	0.8 (3)
C10—C5—C6—C7	0.3 (3)	C17—C18—C19—Cl1	−179.47 (15)
C4—C5—C6—C7	178.96 (18)	C18—C19—C20—C21	−0.4 (3)
O1—C6—C7—C8	179.2 (2)	Cl1—C19—C20—C21	179.86 (16)
C5—C6—C7—C8	0.1 (3)	C19—C20—C21—C16	−0.3 (3)
C6—C7—C8—C9	−0.1 (3)	C17—C16—C21—C20	0.5 (3)
C7—C8—C9—C10	−0.3 (3)	C15—C16—C21—C20	−177.82 (18)
C8—C9—C10—C5	0.7 (3)	N2—C1—N1—C2	178.49 (17)
C6—C5—C10—C9	−0.7 (3)	S1—C1—N1—C2	−0.6 (2)
C4—C5—C10—C9	−179.37 (18)	C3—C2—N1—C1	0.4 (2)
C3—C2—C11—C14	−13.1 (3)	C11—C2—N1—C1	179.96 (16)
N1—C2—C11—C14	167.5 (2)	C5—C4—N2—C1	−179.79 (16)
C3—C2—C11—C13	−133.5 (2)	N1—C1—N2—C4	−2.4 (3)
N1—C2—C11—C13	47.1 (2)	S1—C1—N2—C4	176.66 (14)
C3—C2—C11—C12	110.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.84	1.87	2.611 (2)	147

Experimental details

Crystal data
Chemical formula	C₂₁H₂₀Cl₂N₂OS
M_r	419.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	8.3005 (4), 19.0883 (10), 13.3014 (7)
β (°)	106.121 (1)
V (Å³)	2024.63 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.48 × 0.38 × 0.33

Data collection
Diffractometer	Bruker AXS SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.818, 0.869
No. of measured, independent and observed [I > 2σ(I)] reflections	11999, 4441, 3382
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.110, 1.05
No. of reflections	4441
No. of parameters	248
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.24

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2005).