7-Chloro-4-(2,5-dichloro­phen­yl)-1-phenyl-1H-thio­chromeno[2,3-b]pyridine-2,5(3H,4H)-dione

Wen, L.-R.; Ji, C.; Sun, J.-H.; Xie, H.-Y.

doi:10.1107/S1600536808000573

organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o670

doi:10.1107/S1600536808000573

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7-Chloro-4-(2,5-dichlorophenyl)-1-phenyl-1H-thiochromeno[2,3-b]pyridine-2,5(3H,4H)-dione

Li-Rong Wen,^a ^* Chen Ji,^a Ji-Hui Sun ^a and Huai-Yuan Xie ^a

^aCollege of Chemistry and Molecular Engineering, Qingdao University of, Science and Technology, Qingdao 266042, People's Republic of China
^*Correspondence e-mail: wenlirong@qust.edu.cn

(Received 21 November 2007; accepted 7 January 2008; online 5 March 2008)

In the crystal structure of the title compound, C₂₄H₁₄Cl₃NO₂S, the tetrahydropyridine ring adopts a half-chair conformation and both pendant benzene rings are oriented nearly perpendicular to the thiochromeno[2,3-b]pyridine system.

Related literature

For related literature, see: Ingall et al. (1996 ), Wang et al. (2006 ); Quaglia et al. (2002 ).

Experimental

Crystal data

C₂₄H₁₄Cl₃NO₂S
M_r = 486.77
Monoclinic, P 2₁ /c
a = 13.624 (5) Å
b = 13.474 (5) Å
c = 11.861 (4) Å
β = 95.042 (6)°
V = 2168.9 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.54 mm⁻¹
T = 294 (2) K
0.18 × 0.12 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.909, T_max = 0.948
12228 measured reflections
4426 independent reflections
2650 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.112
S = 0.99
4426 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: SMART (Bruker, 1998 ); cell refinement: SMART; data reduction: SAINT (Bruker, 1999 ); 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 global, I. DOI: 10.1107/S1600536808000573/nc2085sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808000573/nc2085Isup2.hkl

checkCIF report

Comment top

N, S-containing heterocycles shows a wide range of biological activities Ingall et al.,1996). For example, the thiochromones (Wang et al.,2006) as important structural motifs exhibit interesting biological properties and have been tested and applied as drugs (Quaglia et al., 2002). In a continuation of our study of structure-activity, we report here the crystal structure of the title compound,(I), which was synthesized from 3-(2,5- dichlorophenyl)-3-oxo-N-phenylpropanethioamide.

The thiopyran ring is almost planar and the 4H-pyridine ring adpots a half-chair conformation. Both benzene rings are oriented nearly perpendicular to the to the thiochromeno[2,3-b]pyridine ring. The bond length C11—O2(1.21 Å) is shorter than C7—O1(1.24 Å), which might be due to the strong electron withdrawing effect of the nitrogen atom in the pyridine ring.

The interest in the N, S-containing heterocycles has been significantly surged since a wide range of biological activities have been identified (Ingall et al.,1996). For example, the thiochromones (Wang et al.,2006) as important structural motifs exhibit interesting biological properties and have been tested and applied as drugs (Quaglia et al., 2002). In a continuation of our study of structure-activity, we report here the crystal structure of the title compound.

Related literature top

For related literature, see: Ingall et al. (1996), Wang et al. (2006); Quaglia et al. (2002).

Experimental top

3-(2,5-dichlorophenyl)-3-oxo-N-phenylpropanethioamide (1 mmol), 2,5-dichlorobenzaldehyde (1 mmol), (2,2-dimethyl-1,3-dioxane-4,6-dione) (1 mmol) and triethylamine (0.5 mmol)were refluxed in anhydrous alcohol for 8 h. The precipitate was filtered off and dissolved in THF. On slow evaporation of the solvent crystals of the title compound has formed (m.p.498 K).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1999); 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. Crystal structure of the title compound (I) with labeling and displacement ellipsoids drawn at the 50% probability level.

7-Chloro-4-(2,5-dichlorophenyl)-1-phenyl-1H- thiochromeno[2,3-b]pyridine-2,5(3H,4H)-dione top

Crystal data top

C₂₄H₁₄Cl₃NO₂S	F(000) = 992
M_r = 486.77	D_x = 1.491 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2857 reflections
a = 13.624 (5) Å	θ = 2.3–23.4°
b = 13.474 (5) Å	µ = 0.54 mm⁻¹
c = 11.861 (4) Å	T = 294 K
β = 95.042 (6)°	Prism, yellow
V = 2168.9 (14) Å³	0.18 × 0.12 × 0.10 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	4426 independent reflections
Radiation source: fine-focus sealed tube	2650 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ϕ and ω scans	θ_max = 26.5°, θ_min = 1050°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→17
T_min = 0.909, T_max = 0.948	k = −13→16
12228 measured reflections	l = −14→14

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.043	w = 1/[σ²(F_o²) + (0.0479P)² + 0.2323P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.112	(Δ/σ)_max = 0.001
S = 0.99	Δρ_max = 0.28 e Å⁻³
4426 reflections	Δρ_min = −0.26 e Å⁻³
280 parameters

Crystal data top

C₂₄H₁₄Cl₃NO₂S	V = 2168.9 (14) Å³
M_r = 486.77	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.624 (5) Å	µ = 0.54 mm⁻¹
b = 13.474 (5) Å	T = 294 K
c = 11.861 (4) Å	0.18 × 0.12 × 0.10 mm
β = 95.042 (6)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	4426 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2650 reflections with I > 2σ(I)
T_min = 0.909, T_max = 0.948	R_int = 0.049
12228 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 0.99	Δρ_max = 0.28 e Å⁻³
4426 reflections	Δρ_min = −0.26 e Å⁻³
280 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
S1	0.90221 (5)	0.18709 (5)	0.44648 (6)	0.04544 (19)
Cl1	1.15911 (7)	0.38600 (6)	0.09743 (8)	0.0852 (3)
Cl2	0.73863 (7)	0.67908 (6)	0.56211 (8)	0.0848 (3)
Cl3	0.48232 (6)	0.37484 (7)	0.27266 (7)	0.0859 (3)
O1	0.92297 (13)	0.51190 (12)	0.38778 (15)	0.0534 (5)
O2	0.66915 (15)	0.28572 (14)	0.71540 (16)	0.0633 (6)
N1	0.76934 (14)	0.25141 (14)	0.57736 (16)	0.0395 (5)
C1	0.97544 (16)	0.24922 (17)	0.3549 (2)	0.0388 (6)
C2	1.03240 (18)	0.18948 (19)	0.2898 (2)	0.0505 (7)
H2	1.0327	0.1211	0.3004	0.061*
C3	1.0880 (2)	0.2301 (2)	0.2103 (2)	0.0581 (8)
H3	1.1246	0.1896	0.1663	0.070*
C4	1.08877 (19)	0.3324 (2)	0.1967 (2)	0.0524 (7)
C5	1.03478 (18)	0.39236 (19)	0.2611 (2)	0.0464 (6)
H5	1.0366	0.4608	0.2511	0.056*
C6	0.97697 (16)	0.35243 (17)	0.3415 (2)	0.0370 (6)
C7	0.91855 (17)	0.42134 (18)	0.4054 (2)	0.0387 (6)
C8	0.85216 (17)	0.38283 (17)	0.4844 (2)	0.0362 (6)
C9	0.79469 (17)	0.45849 (17)	0.5447 (2)	0.0408 (6)
H9	0.8373	0.5166	0.5583	0.049*
C10	0.77372 (19)	0.41789 (18)	0.6606 (2)	0.0470 (7)
H10A	0.8346	0.4175	0.7097	0.056*
H10B	0.7281	0.4621	0.6940	0.056*
C11	0.73121 (19)	0.31487 (19)	0.6559 (2)	0.0450 (6)
C12	0.83881 (16)	0.28430 (17)	0.50370 (19)	0.0357 (6)
C13	0.73107 (17)	0.15033 (17)	0.56871 (19)	0.0365 (6)
C14	0.7620 (2)	0.0818 (2)	0.6502 (2)	0.0540 (7)
H14	0.8082	0.0993	0.7093	0.065*
C15	0.7234 (2)	−0.0139 (2)	0.6432 (3)	0.0646 (8)
H15	0.7440	−0.0608	0.6978	0.077*
C16	0.6561 (2)	−0.0390 (2)	0.5570 (3)	0.0654 (9)
H16	0.6301	−0.1029	0.5528	0.079*
C17	0.6263 (2)	0.0299 (2)	0.4760 (3)	0.0656 (9)
H17	0.5806	0.0121	0.4167	0.079*
C18	0.6631 (2)	0.1252 (2)	0.4812 (2)	0.0533 (7)
H18	0.6422	0.1716	0.4263	0.064*
C19	0.70135 (18)	0.49370 (19)	0.4760 (2)	0.0430 (6)
C20	0.6704 (2)	0.5922 (2)	0.4790 (2)	0.0545 (7)
C21	0.5847 (3)	0.6240 (2)	0.4178 (3)	0.0715 (9)
H21	0.5663	0.6904	0.4204	0.086*
C22	0.5269 (2)	0.5584 (3)	0.3538 (3)	0.0687 (9)
H22	0.4692	0.5796	0.3132	0.082*
C23	0.55580 (19)	0.4603 (2)	0.3506 (2)	0.0548 (7)
C24	0.64242 (18)	0.4289 (2)	0.4096 (2)	0.0480 (7)
H24	0.6614	0.3629	0.4045	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0490 (4)	0.0304 (3)	0.0585 (4)	−0.0002 (3)	0.0140 (3)	0.0006 (3)
Cl1	0.0958 (6)	0.0721 (6)	0.0966 (6)	−0.0206 (5)	0.0581 (5)	−0.0068 (5)
Cl2	0.0883 (6)	0.0413 (4)	0.1249 (8)	0.0078 (4)	0.0104 (6)	−0.0151 (5)
Cl3	0.0627 (5)	0.1131 (8)	0.0772 (6)	0.0090 (5)	−0.0198 (4)	−0.0077 (5)
O1	0.0648 (12)	0.0295 (10)	0.0678 (12)	0.0001 (8)	0.0161 (10)	0.0042 (9)
O2	0.0759 (14)	0.0576 (13)	0.0610 (12)	−0.0091 (10)	0.0315 (11)	−0.0065 (10)
N1	0.0441 (12)	0.0354 (11)	0.0394 (11)	−0.0040 (10)	0.0067 (10)	−0.0026 (9)
C1	0.0323 (13)	0.0371 (14)	0.0466 (15)	−0.0055 (11)	0.0021 (11)	−0.0025 (12)
C2	0.0500 (16)	0.0335 (14)	0.0698 (18)	−0.0063 (12)	0.0161 (14)	−0.0092 (14)
C3	0.0531 (17)	0.0519 (18)	0.073 (2)	−0.0066 (14)	0.0274 (15)	−0.0147 (15)
C4	0.0494 (17)	0.0490 (17)	0.0612 (18)	−0.0118 (13)	0.0181 (14)	−0.0051 (14)
C5	0.0436 (15)	0.0381 (14)	0.0581 (16)	−0.0082 (12)	0.0075 (13)	0.0000 (13)
C6	0.0302 (13)	0.0336 (13)	0.0465 (14)	−0.0036 (11)	−0.0005 (11)	−0.0006 (12)
C7	0.0369 (14)	0.0339 (14)	0.0444 (15)	−0.0034 (11)	−0.0022 (12)	−0.0012 (12)
C8	0.0353 (13)	0.0316 (13)	0.0408 (14)	0.0005 (11)	−0.0017 (11)	−0.0026 (11)
C9	0.0417 (14)	0.0347 (14)	0.0457 (15)	−0.0015 (11)	0.0024 (12)	−0.0029 (12)
C10	0.0558 (16)	0.0411 (15)	0.0438 (15)	−0.0003 (13)	0.0022 (13)	−0.0073 (12)
C11	0.0522 (16)	0.0462 (16)	0.0355 (14)	0.0019 (13)	−0.0014 (13)	−0.0021 (13)
C12	0.0336 (13)	0.0368 (13)	0.0360 (13)	−0.0020 (11)	−0.0004 (11)	−0.0014 (11)
C13	0.0360 (13)	0.0373 (13)	0.0372 (14)	−0.0044 (11)	0.0083 (11)	−0.0002 (11)
C14	0.0525 (17)	0.0521 (17)	0.0558 (17)	−0.0012 (14)	−0.0050 (14)	0.0090 (15)
C15	0.072 (2)	0.0414 (17)	0.082 (2)	0.0038 (15)	0.0182 (19)	0.0161 (16)
C16	0.069 (2)	0.0457 (18)	0.087 (2)	−0.0152 (16)	0.0352 (19)	−0.0166 (18)
C17	0.066 (2)	0.070 (2)	0.061 (2)	−0.0267 (17)	0.0071 (16)	−0.0144 (18)
C18	0.0604 (18)	0.0563 (18)	0.0424 (16)	−0.0108 (15)	−0.0004 (14)	0.0055 (14)
C19	0.0424 (15)	0.0423 (15)	0.0458 (15)	0.0057 (12)	0.0120 (13)	0.0036 (13)
C20	0.0566 (18)	0.0454 (16)	0.0632 (18)	0.0124 (14)	0.0155 (15)	0.0031 (14)
C21	0.079 (2)	0.057 (2)	0.081 (2)	0.0328 (18)	0.019 (2)	0.0087 (18)
C22	0.058 (2)	0.088 (3)	0.061 (2)	0.0302 (19)	0.0091 (16)	0.0115 (19)
C23	0.0449 (16)	0.073 (2)	0.0468 (16)	0.0085 (15)	0.0052 (13)	0.0046 (15)
C24	0.0444 (16)	0.0506 (16)	0.0495 (16)	0.0099 (13)	0.0063 (13)	0.0027 (14)

Geometric parameters (Å, º) top

S1—C12	1.739 (2)	C9—H9	0.9800
S1—C1	1.751 (2)	C10—C11	1.503 (3)
Cl1—C4	1.739 (3)	C10—H10A	0.9700
Cl2—C20	1.744 (3)	C10—H10B	0.9700
Cl3—C23	1.737 (3)	C13—C18	1.371 (3)
O1—C7	1.240 (3)	C13—C14	1.376 (3)
O2—C11	1.213 (3)	C14—C15	1.393 (4)
N1—C11	1.398 (3)	C14—H14	0.9300
N1—C12	1.414 (3)	C15—C16	1.355 (4)
N1—C13	1.459 (3)	C15—H15	0.9300
C1—C2	1.397 (3)	C16—C17	1.372 (4)
C1—C6	1.400 (3)	C16—H16	0.9300
C2—C3	1.374 (3)	C17—C18	1.377 (4)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.389 (4)	C18—H18	0.9300
C3—H3	0.9300	C19—C24	1.384 (3)
C4—C5	1.370 (3)	C19—C20	1.395 (3)
C5—C6	1.397 (3)	C20—C21	1.387 (4)
C5—H5	0.9300	C21—C22	1.368 (4)
C6—C7	1.475 (3)	C21—H21	0.9300
C7—C8	1.454 (3)	C22—C23	1.382 (4)
C8—C12	1.362 (3)	C22—H22	0.9300
C8—C9	1.504 (3)	C23—C24	1.384 (3)
C9—C19	1.525 (3)	C24—H24	0.9300
C9—C10	1.530 (3)

C12—S1—C1	102.22 (11)	O2—C11—C10	124.3 (2)
C11—N1—C12	121.9 (2)	N1—C11—C10	115.2 (2)
C11—N1—C13	117.80 (19)	C8—C12—N1	121.0 (2)
C12—N1—C13	120.23 (19)	C8—C12—S1	126.18 (19)
C2—C1—C6	119.7 (2)	N1—C12—S1	112.79 (16)
C2—C1—S1	116.23 (18)	C18—C13—C14	120.7 (2)
C6—C1—S1	124.06 (19)	C18—C13—N1	119.8 (2)
C3—C2—C1	121.1 (2)	C14—C13—N1	119.4 (2)
C3—C2—H2	119.4	C13—C14—C15	119.2 (3)
C1—C2—H2	119.4	C13—C14—H14	120.4
C2—C3—C4	119.0 (3)	C15—C14—H14	120.4
C2—C3—H3	120.5	C16—C15—C14	120.2 (3)
C4—C3—H3	120.5	C16—C15—H15	119.9
C5—C4—C3	120.7 (2)	C14—C15—H15	119.9
C5—C4—Cl1	119.2 (2)	C15—C16—C17	119.8 (3)
C3—C4—Cl1	120.1 (2)	C15—C16—H16	120.1
C4—C5—C6	121.1 (2)	C17—C16—H16	120.1
C4—C5—H5	119.5	C16—C17—C18	121.1 (3)
C6—C5—H5	119.4	C16—C17—H17	119.5
C5—C6—C1	118.3 (2)	C18—C17—H17	119.5
C5—C6—C7	118.1 (2)	C13—C18—C17	118.9 (3)
C1—C6—C7	123.6 (2)	C13—C18—H18	120.6
O1—C7—C8	120.1 (2)	C17—C18—H18	120.6
O1—C7—C6	119.8 (2)	C24—C19—C20	117.0 (2)
C8—C7—C6	120.0 (2)	C24—C19—C9	121.5 (2)
C12—C8—C7	123.8 (2)	C20—C19—C9	121.5 (2)
C12—C8—C9	119.9 (2)	C21—C20—C19	121.5 (3)
C7—C8—C9	116.4 (2)	C21—C20—Cl2	118.1 (2)
C8—C9—C19	113.64 (19)	C19—C20—Cl2	120.4 (2)
C8—C9—C10	109.34 (19)	C22—C21—C20	120.5 (3)
C19—C9—C10	112.3 (2)	C22—C21—H21	119.8
C8—C9—H9	107.1	C20—C21—H21	119.8
C19—C9—H9	107.1	C21—C22—C23	118.9 (3)
C10—C9—H9	107.1	C21—C22—H22	120.6
C11—C10—C9	113.5 (2)	C23—C22—H22	120.6
C11—C10—H10A	108.9	C22—C23—C24	120.7 (3)
C9—C10—H10A	108.9	C22—C23—Cl3	119.8 (2)
C11—C10—H10B	108.9	C24—C23—Cl3	119.5 (2)
C9—C10—H10B	108.9	C23—C24—C19	121.4 (3)
H10A—C10—H10B	107.7	C23—C24—H24	119.3
O2—C11—N1	120.6 (2)	C19—C24—H24	119.3

C12—S1—C1—C2	−176.43 (19)	C7—C8—C12—S1	4.3 (3)
C12—S1—C1—C6	1.4 (2)	C9—C8—C12—S1	−177.11 (17)
C6—C1—C2—C3	−1.8 (4)	C11—N1—C12—C8	−17.6 (3)
S1—C1—C2—C3	176.1 (2)	C13—N1—C12—C8	158.9 (2)
C1—C2—C3—C4	1.3 (4)	C11—N1—C12—S1	161.51 (17)
C2—C3—C4—C5	−0.2 (4)	C13—N1—C12—S1	−22.0 (3)
C2—C3—C4—Cl1	179.6 (2)	C1—S1—C12—C8	−4.3 (2)
C3—C4—C5—C6	−0.5 (4)	C1—S1—C12—N1	176.67 (16)
Cl1—C4—C5—C6	179.76 (19)	C11—N1—C13—C18	101.9 (3)
C4—C5—C6—C1	0.0 (4)	C12—N1—C13—C18	−74.8 (3)
C4—C5—C6—C7	−178.2 (2)	C11—N1—C13—C14	−76.6 (3)
C2—C1—C6—C5	1.1 (3)	C12—N1—C13—C14	106.7 (3)
S1—C1—C6—C5	−176.60 (18)	C18—C13—C14—C15	−0.1 (4)
C2—C1—C6—C7	179.3 (2)	N1—C13—C14—C15	178.4 (2)
S1—C1—C6—C7	1.5 (3)	C13—C14—C15—C16	−0.1 (4)
C5—C6—C7—O1	−1.0 (3)	C14—C15—C16—C17	0.5 (4)
C1—C6—C7—O1	−179.1 (2)	C15—C16—C17—C18	−0.7 (4)
C5—C6—C7—C8	175.8 (2)	C14—C13—C18—C17	−0.1 (4)
C1—C6—C7—C8	−2.3 (3)	N1—C13—C18—C17	−178.6 (2)
O1—C7—C8—C12	176.1 (2)	C16—C17—C18—C13	0.5 (4)
C6—C7—C8—C12	−0.7 (3)	C8—C9—C19—C24	38.9 (3)
O1—C7—C8—C9	−2.5 (3)	C10—C9—C19—C24	−85.8 (3)
C6—C7—C8—C9	−179.3 (2)	C8—C9—C19—C20	−142.5 (2)
C12—C8—C9—C19	−95.5 (3)	C10—C9—C19—C20	92.8 (3)
C7—C8—C9—C19	83.2 (3)	C24—C19—C20—C21	−0.3 (4)
C12—C8—C9—C10	30.8 (3)	C9—C19—C20—C21	−179.0 (2)
C7—C8—C9—C10	−150.5 (2)	C24—C19—C20—Cl2	178.93 (19)
C8—C9—C10—C11	−49.6 (3)	C9—C19—C20—Cl2	0.3 (3)
C19—C9—C10—C11	77.5 (3)	C19—C20—C21—C22	1.1 (4)
C12—N1—C11—O2	177.4 (2)	Cl2—C20—C21—C22	−178.2 (2)
C13—N1—C11—O2	0.8 (3)	C20—C21—C22—C23	−0.5 (5)
C12—N1—C11—C10	−3.4 (3)	C21—C22—C23—C24	−1.0 (4)
C13—N1—C11—C10	180.0 (2)	C21—C22—C23—Cl3	178.5 (2)
C9—C10—C11—O2	−143.4 (3)	C22—C23—C24—C19	1.8 (4)
C9—C10—C11—N1	37.4 (3)	Cl3—C23—C24—C19	−177.65 (19)
C7—C8—C12—N1	−176.7 (2)	C20—C19—C24—C23	−1.1 (4)
C9—C8—C12—N1	1.9 (3)	C9—C19—C24—C23	177.5 (2)

Experimental details

Crystal data
Chemical formula	C₂₄H₁₄Cl₃NO₂S
M_r	486.77
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	13.624 (5), 13.474 (5), 11.861 (4)
β (°)	95.042 (6)
V (Å³)	2168.9 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.54
Crystal size (mm)	0.18 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.909, 0.948
No. of measured, independent and observed [I > 2σ(I)] reflections	12228, 4426, 2650
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.112, 0.99
No. of reflections	4426
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.26

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

S1—C12	1.739 (2)	C8—C9	1.504 (3)
S1—C1	1.751 (2)	C9—C10	1.530 (3)
O2—C11	1.213 (3)	C10—C11	1.503 (3)
N1—C11	1.398 (3)

Acknowledgements

The authors are very grateful for financial support by the National Natural Science Foundation of China (No. 20572057), the Natural Science Foundation of Shandong Province (No. Y2006B11) and the Doctoral Foundation of Qingdao University of Science and Technology.

References

Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Wang, W., Li, H., Wang, J. & Zu, L. S. (2006). J. Am. Chem. Soc. 128, 10354–10355. Web of Science CSD CrossRef PubMed CAS Google Scholar

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