1,5-Bis(4-chloro­phen­yl)-3-(2-thien­yl)pentane-1,5-dione

Huang, X.; Xin, F.; Shi, Q.-L.; Wang, Y.; Wei, G.-D.

doi:10.1107/S1600536808038993

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2454

doi:10.1107/S1600536808038993

Open

access

1,5-Bis(4-chlorophenyl)-3-(2-thienyl)pentane-1,5-dione

Xianqiang Huang,^a ^* Feng Xin,^a Qiu-Lan Shi,^b Yong Wang ^a and Guo-Dong Wei ^c

^aDepartment of Chemistry, Liaocheng University, Liaocheng 252059, People's Republic of China, ^bNo.4 Middle School of Liaocheng, Liaocheng 252059, People's Republic of China, and ^cShandong Donge Experimental High School, Donge, Shandong Province,252200, People's Republic of China
^*Correspondence e-mail: hxqiang2005@yahoo.com.cn

(Received 19 October 2008; accepted 20 November 2008; online 26 November 2008)

In the title molecule, C₂₁H₁₆Cl₂O₂S, the five-membered ring is rotationally disordered between two orientations in a 1:1 ratio. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link molecules related by translation along the a axis into chains, which are further combined into layers parallel to the bc plane via C—H⋯π interactions. The crystal studied was a racemic twin with a 0.37 (19):0.63 (19) domain ratio.

Related literature

For the crystal structures of isomers of the title compound, see: Das et al. (1994 ); Huang et al. (2006 ). For details of the synthesis, see Bose et al. (2004 ).

Experimental

Crystal data

C₂₁H₁₆Cl₂O₂S
M_r = 403.30
Orthorhombic, P n a 2₁
a = 7.148 (3) Å
b = 14.128 (6) Å
c = 19.371 (8) Å
V = 1956.3 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.45 mm⁻¹
T = 298 (2) K
0.50 × 0.18 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.806, T_max = 0.935
9549 measured reflections
3430 independent reflections
1466 reflections with I > 2σ(I)
R_int = 0.097

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.248
S = 1.01
3430 reflections
274 parameters
93 restraints
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ); 1650 Friedel pairs
Flack parameter: 0.37 (19)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2ⁱ	0.93	2.33	3.175 (12)	150
C10—H10⋯Cgⁱⁱ	0.93	2.57	3.489 (10)	171
Symmetry codes: (i) x-1, y, z; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ . Cg is the centroid of the C16–C21 ring.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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: 10.1107/S1600536808038993/cv2468sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038993/cv2468Isup2.hkl

checkCIF report

Comment top

In an earlier publication, the "Grindstone Chemistry" method for conducting exothermic reactions in the solvent-free mode has been described (Bose et al., 2004). We tested energy-saving procedures developed in our laboratory for the preparation of 1,5-diketones starting from the fragrant aldehydes and fragrant ketones in the presence of NaOH under solvent-free conditions. Using this method we obtained the title compound, (I).

In (I) (Fig. 1), the bond lengths and angles are normal and correspond to those observed in 1,3,5-triphenyl-pentane-1,5-diketone (Das et al., 1994) and 1,5-diphenyl-3-(2-pyridyl)pentane-1,5-dione (Huang et al., 2006). However, the five-membered ring in (I) is rotationally disordered.

In the crystal, the weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules related by translations along a axis into one-dimensional linear chains, which are further combined into layers parallel to a(b-c) plane via C—H···π interactions (Table 1).

Related literature top

For the crystal structures of isomers of the title compound, see: Das et al. (1994); Huang et al. (2006). For details of the synthesis, see Bose et al. (2004). Cg is the centroid of the C16–C21 ring.

Experimental top

4-Chloroacetophenone (6.25 mmol) and thiophene-2-carbaldehyde (3.125 mmol), NaOH (6.25 mmol) were aggregated with glass paddle in an open flask. The resulting mixture was washed with water for several times for removing NaOH, and recrystalized from ethanol, and afforded the title compound as a crystalline solid. Elemental analysis: calculated for C₂₁ H₁₆ Cl₂O₂ S: C 62.54, H 4.00%; Found: C 62.58, H 4.03%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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. View of (I) showing the atomic labelling and displacement ellipsoids at the 30% level. Only one component of the disordered ring (S1,C1-C4) is shown. Hydrogen atoms are omitted for clarity.

1,5-Bis(4-chlorophenyl)-3-(2-thienyl)pentane-1,5-dione top

Crystal data top

C₂₁H₁₆Cl₂O₂S	D_x = 1.369 Mg m⁻³
M_r = 403.30	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 1035 reflections
a = 7.148 (3) Å	θ = 2.9–18.1°
b = 14.128 (6) Å	µ = 0.45 mm⁻¹
c = 19.371 (8) Å	T = 298 K
V = 1956.3 (14) Å³	Block, colourless
Z = 4	0.50 × 0.18 × 0.15 mm
F(000) = 832

Data collection top

Bruker SMART CCD area-detector diffractometer	3430 independent reflections
Radiation source: fine-focus sealed tube	1466 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.097
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.806, T_max = 0.936	k = −16→13
9549 measured reflections	l = −22→23

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.060	w = 1/[σ²(F_o²)]
wR(F²) = 0.248	(Δ/σ)_max = 0.049
S = 1.01	Δρ_max = 0.22 e Å⁻³
3430 reflections	Δρ_min = −0.24 e Å⁻³
274 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
93 restraints	Extinction coefficient: 0.007 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983); 1650 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.37 (19)

Crystal data top

C₂₁H₁₆Cl₂O₂S	V = 1956.3 (14) Å³
M_r = 403.30	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 7.148 (3) Å	µ = 0.45 mm⁻¹
b = 14.128 (6) Å	T = 298 K
c = 19.371 (8) Å	0.50 × 0.18 × 0.15 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3430 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1466 reflections with I > 2σ(I)
T_min = 0.806, T_max = 0.936	R_int = 0.097
9549 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	H-atom parameters constrained
wR(F²) = 0.248	Δρ_max = 0.22 e Å⁻³
S = 1.01	Δρ_min = −0.24 e Å⁻³
3430 reflections	Absolute structure: Flack (1983); 1650 Friedel pairs
274 parameters	Absolute structure parameter: 0.37 (19)
93 restraints

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	Occ. (<1)
Cl1	0.2204 (5)	0.35740 (19)	0.37574 (14)	0.0939 (10)
Cl2	−0.1208 (5)	0.1215 (2)	1.10502 (16)	0.1172 (13)
O1	0.4870 (9)	0.2902 (4)	0.7007 (3)	0.077 (2)
O2	0.5943 (10)	0.1389 (5)	0.8854 (4)	0.092 (2)
S1'	0.4882 (12)	−0.0928 (5)	0.7244 (4)	0.081 (3)	0.501 (11)
C1'	0.670 (3)	−0.1622 (13)	0.7454 (11)	0.072 (6)	0.501 (11)
H1'	0.6698	−0.2277	0.7403	0.086*	0.501 (11)
C2'	0.818 (3)	−0.1125 (15)	0.7705 (12)	0.089 (6)	0.501 (11)
H2'	0.9278	−0.1396	0.7869	0.106*	0.501 (11)
C3'	0.782 (3)	−0.0134 (17)	0.7684 (14)	0.088 (7)	0.501 (11)
H3'	0.8728	0.0324	0.7770	0.106*	0.501 (11)
S1	0.7978 (12)	−0.0198 (6)	0.7932 (5)	0.107 (3)	0.499 (11)
C1	0.772 (3)	−0.1384 (11)	0.7777 (13)	0.085 (6)	0.499 (11)
H1	0.8553	−0.1848	0.7920	0.102*	0.499 (11)
C2	0.609 (4)	−0.1556 (14)	0.7408 (15)	0.096 (7)	0.499 (11)
H2	0.5705	−0.2157	0.7273	0.116*	0.499 (11)
C3	0.510 (4)	−0.0733 (15)	0.7263 (16)	0.097 (7)	0.499 (11)
H3	0.3984	−0.0724	0.7018	0.116*	0.499 (11)
C4	0.5961 (12)	0.0071 (5)	0.7518 (4)	0.059 (2)
C5	0.5207 (13)	0.1047 (6)	0.7477 (4)	0.058 (2)
H5	0.6228	0.1486	0.7585	0.070*
C6	0.4526 (13)	0.1269 (6)	0.6752 (4)	0.060 (2)
H6A	0.5338	0.0954	0.6424	0.072*
H6B	0.3279	0.1009	0.6696	0.072*
C7	0.4467 (13)	0.2307 (6)	0.6581 (5)	0.058 (2)
C8	0.3898 (11)	0.2589 (6)	0.5866 (4)	0.053 (2)
C9	0.3827 (13)	0.3539 (6)	0.5708 (4)	0.062 (2)
H9	0.4142	0.3983	0.6043	0.074*
C10	0.3292 (14)	0.3844 (7)	0.5056 (5)	0.073 (3)
H10	0.3216	0.4486	0.4957	0.088*
C11	0.2880 (14)	0.3186 (7)	0.4564 (4)	0.067 (2)
C12	0.2986 (13)	0.2235 (6)	0.4700 (5)	0.063 (2)
H12	0.2735	0.1796	0.4354	0.076*
C13	0.3468 (12)	0.1938 (6)	0.5352 (5)	0.062 (2)
H13	0.3506	0.1294	0.5451	0.074*
C14	0.3630 (13)	0.1219 (6)	0.7999 (4)	0.060 (2)
H14A	0.2971	0.1793	0.7872	0.072*
H14B	0.2748	0.0699	0.7972	0.072*
C15	0.4286 (14)	0.1311 (6)	0.8727 (5)	0.064 (2)
C16	0.2903 (16)	0.1309 (5)	0.9295 (4)	0.057 (2)
C17	0.1016 (14)	0.1270 (6)	0.9166 (5)	0.061 (2)
H17	0.0591	0.1252	0.8713	0.073*
C18	−0.0272 (14)	0.1257 (7)	0.9706 (5)	0.077 (3)
H18	−0.1550	0.1233	0.9616	0.092*
C19	0.0376 (16)	0.1278 (6)	1.0372 (5)	0.071 (3)
C20	0.2218 (17)	0.1315 (7)	1.0516 (5)	0.080 (3)
H20	0.2633	0.1324	1.0971	0.096*
C21	0.3488 (14)	0.1341 (7)	0.9974 (4)	0.071 (3)
H21	0.4760	0.1379	1.0070	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.119 (2)	0.0946 (19)	0.0679 (17)	0.0109 (16)	−0.0102 (16)	0.0201 (14)
Cl2	0.114 (3)	0.163 (3)	0.075 (2)	0.021 (2)	0.0267 (17)	−0.0001 (17)
O1	0.106 (6)	0.060 (4)	0.063 (4)	−0.004 (4)	−0.015 (4)	−0.002 (3)
O2	0.063 (5)	0.147 (6)	0.067 (5)	−0.005 (4)	−0.010 (4)	−0.016 (4)
S1'	0.099 (6)	0.075 (5)	0.070 (4)	−0.012 (4)	0.003 (4)	0.007 (3)
C1'	0.091 (12)	0.063 (10)	0.062 (10)	0.013 (9)	0.010 (10)	0.018 (8)
C2'	0.106 (13)	0.077 (11)	0.083 (11)	−0.001 (10)	−0.002 (10)	0.011 (10)
C3'	0.101 (13)	0.081 (12)	0.083 (11)	0.012 (11)	−0.013 (11)	0.009 (10)
S1	0.092 (5)	0.084 (5)	0.146 (8)	0.026 (3)	−0.034 (5)	−0.004 (4)
C1	0.086 (12)	0.048 (10)	0.122 (13)	0.014 (10)	0.005 (11)	0.013 (9)
C2	0.099 (12)	0.072 (11)	0.118 (13)	0.019 (11)	−0.001 (11)	0.016 (10)
C3	0.093 (13)	0.063 (12)	0.135 (14)	0.018 (11)	−0.003 (12)	0.013 (11)
C4	0.056 (6)	0.067 (6)	0.054 (5)	0.000 (5)	−0.006 (4)	0.010 (4)
C5	0.051 (6)	0.061 (5)	0.063 (6)	0.000 (4)	−0.004 (4)	0.003 (4)
C6	0.057 (6)	0.064 (6)	0.058 (6)	−0.002 (4)	0.005 (4)	0.011 (4)
C7	0.054 (6)	0.067 (6)	0.055 (5)	0.009 (5)	0.003 (4)	0.016 (5)
C8	0.044 (5)	0.060 (6)	0.056 (5)	0.006 (4)	0.000 (4)	0.010 (5)
C9	0.065 (6)	0.059 (6)	0.062 (6)	0.000 (5)	−0.016 (5)	−0.001 (4)
C10	0.081 (8)	0.069 (6)	0.070 (7)	0.004 (5)	−0.009 (6)	0.016 (5)
C11	0.076 (7)	0.069 (6)	0.057 (6)	−0.002 (5)	−0.001 (5)	0.015 (5)
C12	0.057 (6)	0.071 (6)	0.062 (6)	0.001 (5)	0.004 (4)	0.005 (5)
C13	0.061 (7)	0.061 (6)	0.064 (6)	0.010 (4)	0.004 (4)	0.006 (5)
C14	0.060 (6)	0.070 (6)	0.051 (5)	0.001 (4)	−0.008 (4)	0.004 (4)
C15	0.059 (6)	0.082 (6)	0.050 (5)	0.003 (5)	−0.009 (5)	−0.005 (4)
C16	0.074 (7)	0.049 (5)	0.047 (5)	0.002 (5)	−0.007 (5)	−0.007 (4)
C17	0.068 (7)	0.067 (6)	0.048 (5)	0.013 (5)	−0.003 (5)	0.002 (4)
C18	0.056 (7)	0.106 (8)	0.068 (7)	0.009 (5)	−0.004 (6)	0.002 (5)
C19	0.092 (9)	0.064 (6)	0.058 (6)	0.001 (5)	0.005 (6)	−0.015 (4)
C20	0.090 (9)	0.106 (8)	0.044 (5)	−0.015 (6)	−0.009 (6)	0.003 (5)
C21	0.070 (7)	0.090 (7)	0.053 (6)	−0.007 (5)	−0.013 (5)	−0.009 (4)

Geometric parameters (Å, º) top

Cl1—C11	1.724 (9)	C6—H6B	0.9700
Cl2—C19	1.736 (11)	C7—C8	1.498 (11)
O1—C7	1.213 (10)	C8—C9	1.377 (10)
O2—C15	1.215 (10)	C8—C13	1.389 (11)
S1'—C1'	1.678 (16)	C9—C10	1.387 (12)
S1'—C4	1.694 (10)	C9—H9	0.9300
C1'—C2'	1.359 (17)	C10—C11	1.364 (13)
C1'—H1'	0.9300	C10—H10	0.9300
C2'—C3'	1.423 (18)	C11—C12	1.371 (12)
C2'—H2'	0.9300	C12—C13	1.376 (12)
C3'—C4	1.401 (18)	C12—H12	0.9300
C3'—H3'	0.9300	C13—H13	0.9300
S1—C4	1.693 (10)	C14—C15	1.490 (12)
S1—C1	1.713 (16)	C14—H14A	0.9700
C1—C2	1.385 (18)	C14—H14B	0.9700
C1—H1	0.9300	C15—C16	1.479 (13)
C2—C3	1.390 (18)	C16—C17	1.373 (12)
C2—H2	0.9300	C16—C21	1.381 (12)
C3—C4	1.383 (19)	C17—C18	1.393 (13)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.482 (10)	C18—C19	1.372 (14)
C5—C6	1.518 (11)	C18—H18	0.9300
C5—C14	1.535 (13)	C19—C20	1.347 (14)
C5—H5	0.9800	C20—C21	1.389 (14)
C6—C7	1.504 (10)	C20—H20	0.9300
C6—H6A	0.9700	C21—H21	0.9300

C1'—S1'—C4	93.3 (9)	C9—C8—C13	118.6 (7)
C2'—C1'—S1'	112.8 (13)	C9—C8—C7	118.3 (7)
C2'—C1'—H1'	123.6	C13—C8—C7	123.1 (7)
S1'—C1'—H1'	123.6	C8—C9—C10	120.9 (8)
C1'—C2'—C3'	111.1 (17)	C8—C9—H9	119.5
C1'—C2'—H2'	124.5	C10—C9—H9	119.5
C3'—C2'—H2'	124.4	C11—C10—C9	119.0 (9)
C4—C3'—C2'	112.3 (17)	C11—C10—H10	120.5
C4—C3'—H3'	123.8	C9—C10—H10	120.5
C2'—C3'—H3'	123.8	C10—C11—C12	121.4 (8)
C4—S1—C1	92.5 (9)	C10—C11—Cl1	118.6 (7)
C2—C1—S1	110.7 (13)	C12—C11—Cl1	120.1 (7)
C2—C1—H1	124.6	C11—C12—C13	119.3 (9)
S1—C1—H1	124.6	C11—C12—H12	120.4
C1—C2—C3	112.6 (17)	C13—C12—H12	120.4
C1—C2—H2	123.7	C12—C13—C8	120.7 (8)
C3—C2—H2	123.7	C12—C13—H13	119.6
C4—C3—C2	112.9 (18)	C8—C13—H13	119.6
C4—C3—H3	123.5	C15—C14—C5	114.0 (8)
C2—C3—H3	123.5	C15—C14—H14A	108.8
C3—C4—C3'	109.4 (15)	C5—C14—H14A	108.8
C3—C4—C5	125.7 (13)	C15—C14—H14B	108.8
C3'—C4—C5	123.5 (12)	C5—C14—H14B	108.8
C3—C4—S1	111.3 (12)	H14A—C14—H14B	107.7
C3'—C4—S1	15.2 (13)	O2—C15—C16	120.0 (9)
C5—C4—S1	123.0 (7)	O2—C15—C14	120.4 (9)
C3—C4—S1'	2.8 (15)	C16—C15—C14	119.6 (9)
C3'—C4—S1'	109.4 (11)	C17—C16—C21	118.1 (9)
C5—C4—S1'	126.3 (7)	C17—C16—C15	121.4 (8)
S1—C4—S1'	110.4 (6)	C21—C16—C15	120.4 (9)
C4—C5—C6	111.1 (7)	C16—C17—C18	120.9 (8)
C4—C5—C14	112.3 (7)	C16—C17—H17	119.5
C6—C5—C14	109.9 (7)	C18—C17—H17	119.5
C4—C5—H5	107.8	C19—C18—C17	118.9 (9)
C6—C5—H5	107.8	C19—C18—H18	120.6
C14—C5—H5	107.8	C17—C18—H18	120.6
C7—C6—C5	114.5 (7)	C20—C19—C18	121.7 (10)
C7—C6—H6A	108.6	C20—C19—Cl2	118.9 (8)
C5—C6—H6A	108.6	C18—C19—Cl2	119.4 (9)
C7—C6—H6B	108.6	C19—C20—C21	118.9 (9)
C5—C6—H6B	108.6	C19—C20—H20	120.6
H6A—C6—H6B	107.6	C21—C20—H20	120.6
O1—C7—C8	120.7 (8)	C16—C21—C20	121.5 (10)
O1—C7—C6	121.2 (8)	C16—C21—H21	119.3
C8—C7—C6	118.1 (8)	C20—C21—H21	119.3

C4—S1'—C1'—C2'	−2.6 (7)	C5—C6—C7—C8	177.1 (8)
S1'—C1'—C2'—C3'	−3.5 (9)	O1—C7—C8—C9	−0.6 (13)
C1'—C2'—C3'—C4	9.7 (17)	C6—C7—C8—C9	179.5 (8)
C4—S1—C1—C2	0.2 (7)	O1—C7—C8—C13	178.3 (9)
S1—C1—C2—C3	−0.1 (10)	C6—C7—C8—C13	−1.5 (12)
C1—C2—C3—C4	−0.1 (19)	C13—C8—C9—C10	1.6 (14)
C2—C3—C4—C3'	16 (3)	C7—C8—C9—C10	−179.4 (9)
C2—C3—C4—C5	−176.9 (13)	C8—C9—C10—C11	−1.7 (16)
C2—C3—C4—S1	0 (2)	C9—C10—C11—C12	0.0 (16)
C2—C3—C4—S1'	−73 (26)	C9—C10—C11—Cl1	179.6 (8)
C2'—C3'—C4—C3	−14 (2)	C10—C11—C12—C13	1.8 (14)
C2'—C3'—C4—C5	178.6 (12)	Cl1—C11—C12—C13	−177.8 (8)
C2'—C3'—C4—S1	85 (5)	C11—C12—C13—C8	−1.9 (14)
C2'—C3'—C4—S1'	−11.3 (19)	C9—C8—C13—C12	0.2 (13)
C1—S1—C4—C3	−0.3 (15)	C7—C8—C13—C12	−178.8 (9)
C1—S1—C4—C3'	−86 (4)	C4—C5—C14—C15	73.6 (9)
C1—S1—C4—C5	176.9 (11)	C6—C5—C14—C15	−162.3 (7)
C1—S1—C4—S1'	2.5 (10)	C5—C14—C15—O2	11.0 (12)
C1'—S1'—C4—C3	100 (27)	C5—C14—C15—C16	−169.3 (7)
C1'—S1'—C4—C3'	7.9 (13)	O2—C15—C16—C17	176.7 (8)
C1'—S1'—C4—C5	177.6 (10)	C14—C15—C16—C17	−3.1 (12)
C1'—S1'—C4—S1	−8.2 (9)	O2—C15—C16—C21	−3.8 (13)
C3—C4—C5—C6	−47.4 (19)	C14—C15—C16—C21	176.4 (8)
C3'—C4—C5—C6	117.6 (16)	C21—C16—C17—C18	−0.4 (12)
S1—C4—C5—C6	135.8 (8)	C15—C16—C17—C18	179.1 (8)
S1'—C4—C5—C6	−50.7 (11)	C16—C17—C18—C19	−0.3 (13)
C3—C4—C5—C14	76.2 (18)	C17—C18—C19—C20	0.2 (14)
C3'—C4—C5—C14	−118.8 (15)	C17—C18—C19—Cl2	−177.5 (7)
S1—C4—C5—C14	−100.6 (9)	C18—C19—C20—C21	0.6 (14)
S1'—C4—C5—C14	72.9 (10)	Cl2—C19—C20—C21	178.3 (7)
C4—C5—C6—C7	−156.7 (8)	C17—C16—C21—C20	1.2 (13)
C14—C5—C6—C7	78.5 (10)	C15—C16—C21—C20	−178.3 (8)
C5—C6—C7—O1	−2.7 (13)	C19—C20—C21—C16	−1.3 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2ⁱ	0.93	2.33	3.175 (12)	150
C10—H10···Cgⁱⁱ	0.93	2.57	3.489 (10)	171

Symmetry codes: (i) x−1, y, z; (ii) −x+1/2, y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₆Cl₂O₂S
M_r	403.30
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	298
a, b, c (Å)	7.148 (3), 14.128 (6), 19.371 (8)
V (Å³)	1956.3 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.45
Crystal size (mm)	0.50 × 0.18 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.806, 0.936
No. of measured, independent and observed [I > 2σ(I)] reflections	9549, 3430, 1466
R_int	0.097
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.248, 1.01
No. of reflections	3430
No. of parameters	274
No. of restraints	93
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.24
Absolute structure	Flack (1983); 1650 Friedel pairs
Absolute structure parameter	0.37 (19)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2ⁱ	0.93	2.33	3.175 (12)	150.4
C10—H10···Cgⁱⁱ	0.93	2.57	3.489 (10)	171.0

Symmetry codes: (i) x−1, y, z; (ii) −x+1/2, y+1/2, z−1/2.

Acknowledgements

The authors acknowledge the financial support of the University Student Science and Technology Culture Foundation of Liaocheng University (grant No. SRT07013HX2).

References

Bose, A. K., Pednekar, S., Ganguly, S. N., Chakraborty, G. & Manhas, M. S. (2004). Tetrahedron Lett. 45, 8351–8353. Web of Science CrossRef CAS Google Scholar
Das, G. C., Hursthouse, M. B., Malik, K. M. A., Rahman, M. M., Rahman, M. T. & Olsson, T. (1994). J. Chem. Crystallogr. 24, 511–515. CSD CrossRef CAS Web of Science Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Huang, X.-Q., Wang, D.-Q., Dou, J.-M. & Wang, J.-X. (2006). Acta Cryst. E62, o60–o61. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1995). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar