3-Phenyl-1,5-di-2-thienylpentane-1,5-dione

Meng, T.-J.; Huang, X.-Q.; He, Q.-P.; Wang, J.-Y.

doi:10.1107/S1600536808009884

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o853

doi:10.1107/S1600536808009884

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3-Phenyl-1,5-di-2-thienylpentane-1,5-dione

Tuan-Jie Meng,^a Xian-Qiang Huang,^b ^* Qing-Peng He ^b and Jian-Yong Wang ^b

^aDepartment of Chemistry, Shangqiu Normal University, Shangqiu Henan Province 476000, People's Republic of China, and ^bDepartment of Chemistry, Liaocheng University, Liaocheng 252059, People's Republic of China
^*Correspondence e-mail: hxqqxh2008@163.com

(Received 25 March 2008; accepted 10 April 2008; online 16 April 2008)

The asymmetric unit of the title compound, C₁₉H₁₆O₂S₂, contains two independent molecules with slightly different conformations. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds [C⋯O = 3.279 (15) and 3.407 (16) Å] link the molecules into chains extended along the c axis.

Related literature

For related crystal structures, see: Das et al. (1994 ); Huang et al. (2006 ). For general background, see: Bose et al. (2004 ).

Experimental

Crystal data

C₁₉H₁₆O₂S₂
M_r = 340.44
Orthorhombic, P n a 2₁
a = 27.912 (3) Å
b = 5.8607 (8) Å
c = 20.841 (2) Å
V = 3409.2 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 298 (2) K
0.26 × 0.17 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.922, T_max = 0.972
13190 measured reflections
5636 independent reflections
2006 reflections with I > 2σ(I)
R_int = 0.120

Refinement

R[F² > 2σ(F²)] = 0.086
wR(F²) = 0.192
S = 1.02
5636 reflections
415 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.45 e Å⁻³
Absolute structure: Flack (1983 ), 2565 Friedel pairs
Flack parameter: 0.18 (15)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯O4ⁱ	0.93	2.58	3.407 (16)	149
C1—H1⋯O2ⁱⁱ	0.93	2.54	3.279 (15)	137
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, -y+1, z-{\script{1\over 2}}]$ .

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/S1600536808009884/cv2395sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009884/cv2395Isup2.hkl

checkCIF report

Comment top

In continuation of our ongoing program directed to the development of environmentally benign methods of chemical synthesis (Bose et al., 2004), we have discovered a convenient one-step method 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, which can be considered as a general method for the synthesis of 1,5-diketones, we obtained the title compound, (I). We present here its crystal structure.

In (I) (Fig. 1), the asymmetric unit contains two independent molecules with slightly different conformations and normal bond lengths and angles comparable 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). The weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into one-dimensional chains extending along the c axis.

Related literature top

For related crystal structures, see: Das et al. (1994); Huang et al. (2006). For general background, see Bose et al. (2004).

Experimental top

2-Acetylthiophene (6.25 mmol) and freshly distilled benzaldehyde (3.125 mmol), NaOH (0.25 g, 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 crystalline solid. Elemental analysis: calculated for C₁₉H₁₆O₂S₂: C 67.03, H 4.74%; Found: C 67.08, H 4.72%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (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. Drawing of the title compound with atomic numbering scheme and 30% probability displacement ellipsoids. Hydrogen atoms are omitted for clarity.

3-Phenyl-1,5-di-2-thienylpentane-1,5-dione top

Crystal data top

C₁₉H₁₆O₂S₂	D_x = 1.327 Mg m⁻³
M_r = 340.44	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 1120 reflections
a = 27.912 (3) Å	θ = 2.9–25.0°
b = 5.8607 (8) Å	µ = 0.32 mm⁻¹
c = 20.841 (2) Å	T = 298 K
V = 3409.2 (7) Å³	Block, yellow
Z = 8	0.26 × 0.17 × 0.09 mm
F(000) = 1424

Data collection top

Bruker SMART CCD area-detector diffractometer	5636 independent reflections
Radiation source: fine-focus sealed tube	2006 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.120
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→33
T_min = 0.922, T_max = 0.972	k = −6→6
13190 measured reflections	l = −24→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.086	H-atom parameters constrained
wR(F²) = 0.192	w = 1/[σ²(F_o²) + (0.0478P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
5636 reflections	Δρ_max = 0.36 e Å⁻³
415 parameters	Δρ_min = −0.45 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2565 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.18 (15)

Crystal data top

C₁₉H₁₆O₂S₂	V = 3409.2 (7) Å³
M_r = 340.44	Z = 8
Orthorhombic, Pna2₁	Mo Kα radiation
a = 27.912 (3) Å	µ = 0.32 mm⁻¹
b = 5.8607 (8) Å	T = 298 K
c = 20.841 (2) Å	0.26 × 0.17 × 0.09 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	5636 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2006 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.972	R_int = 0.120
13190 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.086	H-atom parameters constrained
wR(F²) = 0.192	Δρ_max = 0.36 e Å⁻³
S = 1.02	Δρ_min = −0.45 e Å⁻³
5636 reflections	Absolute structure: Flack (1983), 2565 Friedel pairs
415 parameters	Absolute structure parameter: 0.18 (15)
1 restraint

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
O1	0.4895 (3)	0.4760 (15)	−0.0653 (3)	0.100 (3)
O2	0.5431 (3)	0.5207 (16)	0.1105 (5)	0.117 (3)
O3	0.2607 (3)	1.1103 (14)	0.1107 (3)	0.093 (2)
O4	0.2020 (3)	0.8734 (18)	−0.0734 (4)	0.117 (3)
S1	0.49589 (12)	0.5733 (5)	−0.20432 (17)	0.0981 (11)
S2	0.62799 (13)	0.6688 (7)	0.18264 (19)	0.1168 (13)
S3	0.25330 (11)	1.0432 (5)	0.24992 (17)	0.0937 (10)
S4	0.11681 (15)	0.6173 (10)	−0.1171 (2)	0.1467 (19)
C1	0.4854 (4)	0.772 (2)	−0.2610 (6)	0.091 (4)
H1	0.4894	0.7482	−0.3048	0.109*
C2	0.4704 (4)	0.969 (2)	−0.2348 (6)	0.081 (3)
H2	0.4640	1.1001	−0.2585	0.098*
C3	0.4655 (4)	0.957 (2)	−0.1689 (6)	0.078 (3)
H3	0.4550	1.0777	−0.1436	0.094*
C4	0.4779 (3)	0.747 (2)	−0.1452 (6)	0.064 (3)
C5	0.4773 (4)	0.676 (2)	−0.0809 (6)	0.074 (3)
C6	0.4575 (4)	0.8254 (19)	−0.0275 (5)	0.075 (3)
H6A	0.4648	0.9830	−0.0378	0.089*
H6B	0.4229	0.8103	−0.0276	0.089*
C7	0.4748 (4)	0.7802 (17)	0.0391 (5)	0.058 (3)
H7	0.4733	0.6147	0.0455	0.070*
C8	0.5276 (3)	0.8490 (17)	0.0456 (5)	0.064 (3)
H8A	0.5434	0.8245	0.0047	0.077*
H8B	0.5293	1.0107	0.0552	0.077*
C9	0.5549 (4)	0.718 (2)	0.0976 (6)	0.075 (4)
C10	0.5955 (4)	0.820 (2)	0.1275 (5)	0.087 (4)
C11	0.6126 (4)	1.045 (2)	0.1228 (6)	0.090 (4)
H11	0.5995	1.1584	0.0970	0.108*
C12	0.6526 (5)	1.072 (2)	0.1631 (7)	0.102 (4)
H12	0.6699	1.2077	0.1654	0.123*
C13	0.6638 (4)	0.890 (2)	0.1975 (6)	0.107 (4)
H13	0.6890	0.8860	0.2268	0.128*
C14	0.4456 (3)	0.8857 (19)	0.0911 (6)	0.061 (3)
C15	0.4379 (4)	0.782 (2)	0.1486 (7)	0.078 (3)
H15	0.4512	0.6389	0.1559	0.093*
C16	0.4109 (4)	0.883 (3)	0.1972 (7)	0.095 (4)
H16	0.4060	0.8063	0.2356	0.114*
C17	0.3914 (5)	1.096 (3)	0.1884 (7)	0.100 (5)
H17	0.3740	1.1666	0.2210	0.121*
C18	0.3979 (4)	1.200 (2)	0.1324 (8)	0.088 (4)
H18	0.3832	1.3399	0.1258	0.105*
C19	0.4253 (4)	1.1110 (19)	0.0834 (6)	0.083 (3)
H19	0.4307	1.1945	0.0462	0.100*
C20	0.2648 (4)	0.857 (3)	0.3085 (5)	0.099 (4)
H20	0.2570	0.8801	0.3514	0.119*
C21	0.2870 (4)	0.667 (2)	0.2862 (7)	0.094 (4)
H21	0.2972	0.5507	0.3135	0.113*
C22	0.2936 (3)	0.6553 (17)	0.2214 (4)	0.049 (3)
H22	0.3067	0.5334	0.1988	0.058*
C23	0.2767 (3)	0.8648 (17)	0.1944 (5)	0.059 (3)
C24	0.2767 (3)	0.925 (2)	0.1271 (6)	0.067 (3)
C25	0.2983 (4)	0.7695 (18)	0.0785 (5)	0.069 (3)
H25A	0.3320	0.8066	0.0746	0.083*
H25B	0.2961	0.6145	0.0946	0.083*
C26	0.2767 (3)	0.7758 (17)	0.0135 (5)	0.060 (3)
H26	0.2717	0.9366	0.0024	0.072*
C27	0.2264 (4)	0.6603 (19)	0.0151 (5)	0.072 (3)
H27A	0.2310	0.4973	0.0203	0.087*
H27B	0.2095	0.7148	0.0527	0.087*
C28	0.1956 (5)	0.698 (3)	−0.0415 (7)	0.090 (4)
C29	0.1564 (5)	0.554 (4)	−0.0595 (8)	0.125 (6)
C30	0.1481 (6)	0.341 (4)	−0.0319 (8)	0.141 (7)
H30	0.1666	0.2724	0.0000	0.169*
C31	0.1071 (6)	0.247 (3)	−0.0608 (8)	0.141 (7)
H31	0.0953	0.1058	−0.0480	0.169*
C32	0.0852 (6)	0.368 (3)	−0.1074 (9)	0.144 (7)
H32	0.0581	0.3241	−0.1302	0.173*
C33	0.3080 (3)	0.6706 (19)	−0.0394 (5)	0.054 (3)
C34	0.3164 (4)	0.7746 (18)	−0.0964 (6)	0.066 (3)
H34	0.3017	0.9139	−0.1048	0.079*
C35	0.3456 (5)	0.683 (3)	−0.1420 (6)	0.086 (4)
H35	0.3525	0.7628	−0.1793	0.103*
C36	0.3646 (4)	0.470 (3)	−0.1320 (7)	0.098 (4)
H36	0.3828	0.4010	−0.1638	0.117*
C37	0.3570 (4)	0.364 (2)	−0.0771 (7)	0.088 (4)
H37	0.3719	0.2247	−0.0703	0.106*
C38	0.3279 (4)	0.4499 (18)	−0.0293 (5)	0.071 (3)
H38	0.3216	0.3671	0.0078	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.139 (7)	0.062 (6)	0.100 (6)	0.030 (5)	−0.003 (5)	−0.002 (5)
O2	0.103 (7)	0.085 (7)	0.163 (8)	−0.004 (5)	−0.025 (6)	0.055 (6)
O3	0.127 (7)	0.055 (6)	0.096 (6)	−0.017 (5)	−0.016 (5)	−0.007 (5)
O4	0.072 (6)	0.154 (10)	0.125 (8)	0.003 (6)	0.026 (5)	0.043 (7)
S1	0.127 (3)	0.068 (2)	0.100 (2)	0.006 (2)	0.014 (2)	−0.017 (2)
S2	0.098 (3)	0.120 (3)	0.133 (3)	0.028 (2)	−0.036 (2)	−0.004 (3)
S3	0.102 (2)	0.085 (2)	0.094 (2)	0.001 (2)	−0.003 (2)	−0.020 (2)
S4	0.077 (3)	0.214 (5)	0.149 (4)	−0.018 (3)	0.024 (3)	−0.068 (4)
C1	0.115 (10)	0.074 (10)	0.083 (10)	−0.017 (8)	0.020 (8)	−0.015 (8)
C2	0.108 (9)	0.056 (9)	0.080 (10)	0.004 (7)	0.004 (8)	0.009 (7)
C3	0.091 (9)	0.071 (10)	0.072 (9)	0.007 (7)	0.003 (7)	−0.005 (8)
C4	0.046 (6)	0.090 (11)	0.056 (8)	−0.007 (6)	−0.005 (6)	−0.001 (7)
C5	0.063 (8)	0.059 (8)	0.100 (10)	0.015 (6)	−0.009 (7)	−0.021 (8)
C6	0.074 (7)	0.073 (8)	0.076 (9)	0.013 (6)	−0.008 (7)	−0.011 (7)
C7	0.068 (8)	0.047 (7)	0.060 (7)	−0.002 (5)	−0.008 (7)	0.000 (5)
C8	0.062 (8)	0.065 (8)	0.066 (7)	−0.005 (6)	−0.004 (6)	0.011 (6)
C9	0.042 (7)	0.089 (10)	0.094 (10)	0.010 (7)	0.009 (7)	0.017 (8)
C10	0.067 (9)	0.085 (10)	0.109 (10)	0.023 (8)	−0.022 (7)	−0.013 (8)
C11	0.077 (9)	0.083 (10)	0.110 (10)	0.016 (8)	−0.016 (8)	−0.022 (8)
C12	0.091 (10)	0.088 (11)	0.128 (12)	0.010 (8)	−0.020 (9)	−0.017 (9)
C13	0.087 (10)	0.107 (12)	0.125 (11)	0.026 (9)	−0.024 (8)	−0.023 (10)
C14	0.056 (7)	0.054 (8)	0.072 (9)	−0.004 (6)	−0.015 (6)	−0.004 (7)
C15	0.083 (9)	0.065 (8)	0.085 (10)	−0.002 (7)	−0.014 (8)	0.005 (8)
C16	0.068 (9)	0.124 (14)	0.094 (11)	−0.019 (9)	0.000 (8)	0.003 (10)
C17	0.076 (9)	0.149 (16)	0.077 (11)	−0.008 (10)	0.008 (8)	−0.025 (11)
C18	0.076 (9)	0.088 (10)	0.099 (11)	0.009 (7)	−0.006 (8)	−0.032 (10)
C19	0.105 (10)	0.051 (9)	0.093 (9)	−0.005 (7)	0.002 (8)	−0.018 (7)
C20	0.076 (8)	0.176 (15)	0.046 (8)	0.022 (9)	0.006 (6)	−0.008 (9)
C21	0.073 (8)	0.087 (10)	0.123 (13)	−0.017 (7)	0.022 (8)	0.012 (10)
C22	0.067 (7)	0.053 (7)	0.026 (6)	−0.008 (5)	0.001 (5)	0.002 (5)
C23	0.052 (6)	0.074 (8)	0.050 (7)	0.013 (5)	−0.011 (6)	−0.003 (6)
C24	0.054 (7)	0.048 (8)	0.098 (10)	−0.002 (6)	−0.006 (6)	0.010 (8)
C25	0.074 (8)	0.069 (8)	0.064 (8)	−0.016 (6)	−0.002 (7)	−0.011 (6)
C26	0.052 (7)	0.057 (7)	0.069 (8)	−0.001 (5)	0.004 (6)	0.013 (6)
C27	0.066 (8)	0.084 (9)	0.067 (8)	−0.001 (6)	0.004 (6)	0.002 (6)
C28	0.091 (10)	0.103 (11)	0.076 (10)	−0.019 (9)	−0.007 (8)	0.008 (8)
C29	0.057 (10)	0.182 (19)	0.134 (15)	0.002 (12)	0.018 (10)	−0.077 (14)
C30	0.078 (12)	0.18 (2)	0.163 (17)	0.000 (13)	0.018 (11)	−0.081 (15)
C31	0.079 (13)	0.19 (2)	0.159 (17)	−0.002 (12)	0.017 (11)	−0.078 (15)
C32	0.080 (12)	0.19 (2)	0.161 (17)	0.004 (12)	0.023 (11)	−0.088 (14)
C33	0.046 (6)	0.064 (8)	0.052 (7)	0.011 (5)	0.002 (5)	−0.006 (6)
C34	0.075 (8)	0.059 (8)	0.063 (9)	0.015 (6)	0.004 (7)	0.015 (6)
C35	0.091 (10)	0.109 (13)	0.058 (9)	0.012 (8)	−0.020 (8)	0.005 (8)
C36	0.085 (9)	0.134 (16)	0.074 (10)	−0.019 (10)	0.004 (8)	−0.043 (10)
C37	0.092 (10)	0.084 (10)	0.088 (10)	−0.024 (8)	0.012 (9)	−0.039 (10)
C38	0.093 (8)	0.039 (7)	0.083 (9)	−0.013 (6)	0.001 (7)	−0.002 (6)

Geometric parameters (Å, º) top

O1—C5	1.263 (12)	C16—H16	0.9300
O2—C9	1.232 (12)	C17—C18	1.328 (16)
O3—C24	1.225 (11)	C17—H17	0.9300
O4—C28	1.239 (13)	C18—C19	1.376 (14)
S1—C4	1.674 (11)	C18—H18	0.9300
S1—C1	1.683 (13)	C19—H19	0.9300
S2—C13	1.667 (14)	C20—C21	1.356 (15)
S2—C10	1.712 (11)	C20—H20	0.9300
S3—C20	1.671 (13)	C21—C22	1.364 (13)
S3—C23	1.692 (10)	C21—H21	0.9300
S4—C29	1.672 (17)	C22—C23	1.430 (12)
S4—C32	1.72 (2)	C22—H22	0.9300
C1—C2	1.346 (14)	C23—C24	1.445 (14)
C1—H1	0.9300	C24—C25	1.488 (14)
C2—C3	1.380 (12)	C25—C26	1.484 (12)
C2—H2	0.9300	C25—H25A	0.9700
C3—C4	1.373 (13)	C25—H25B	0.9700
C3—H3	0.9300	C26—C33	1.536 (13)
C4—C5	1.404 (15)	C26—C27	1.557 (12)
C5—C6	1.520 (14)	C26—H26	0.9800
C6—C7	1.493 (13)	C27—C28	1.477 (16)
C6—H6A	0.9700	C27—H27A	0.9700
C6—H6B	0.9700	C27—H27B	0.9700
C7—C14	1.489 (13)	C28—C29	1.433 (19)
C7—C8	1.534 (12)	C29—C30	1.39 (2)
C7—H7	0.9800	C30—C31	1.41 (2)
C8—C9	1.530 (14)	C30—H30	0.9300
C8—H8A	0.9700	C31—C32	1.35 (2)
C8—H8B	0.9700	C31—H31	0.9300
C9—C10	1.425 (15)	C32—H32	0.9300
C10—C11	1.405 (15)	C33—C34	1.357 (13)
C11—C12	1.408 (15)	C33—C38	1.423 (13)
C11—H11	0.9300	C34—C35	1.362 (14)
C12—C13	1.323 (15)	C34—H34	0.9300
C12—H12	0.9300	C35—C36	1.368 (16)
C13—H13	0.9300	C35—H35	0.9300
C14—C15	1.361 (14)	C36—C37	1.318 (15)
C14—C19	1.446 (14)	C36—H36	0.9300
C15—C16	1.394 (15)	C37—C38	1.379 (14)
C15—H15	0.9300	C37—H37	0.9300
C16—C17	1.374 (17)	C38—H38	0.9300

C4—S1—C1	92.5 (6)	C18—C19—H19	120.6
C13—S2—C10	92.3 (7)	C14—C19—H19	120.6
C20—S3—C23	91.2 (6)	C21—C20—S3	112.0 (10)
C29—S4—C32	93.7 (10)	C21—C20—H20	124.0
C2—C1—S1	111.3 (10)	S3—C20—H20	124.0
C2—C1—H1	124.3	C20—C21—C22	116.1 (13)
S1—C1—H1	124.3	C20—C21—H21	121.9
C1—C2—C3	113.0 (12)	C22—C21—H21	121.9
C1—C2—H2	123.5	C21—C22—C23	107.7 (10)
C3—C2—H2	123.5	C21—C22—H22	126.2
C4—C3—C2	112.2 (11)	C23—C22—H22	126.2
C4—C3—H3	123.9	C22—C23—C24	126.2 (9)
C2—C3—H3	123.9	C22—C23—S3	112.8 (8)
C3—C4—C5	127.3 (11)	C24—C23—S3	120.9 (8)
C3—C4—S1	110.9 (9)	O3—C24—C23	119.1 (11)
C5—C4—S1	121.8 (10)	O3—C24—C25	120.0 (11)
O1—C5—C4	121.0 (11)	C23—C24—C25	120.7 (10)
O1—C5—C6	116.4 (12)	C26—C25—C24	116.2 (10)
C4—C5—C6	122.3 (11)	C26—C25—H25A	108.2
C7—C6—C5	117.4 (10)	C24—C25—H25A	108.2
C7—C6—H6A	107.9	C26—C25—H25B	108.2
C5—C6—H6A	107.9	C24—C25—H25B	108.2
C7—C6—H6B	107.9	H25A—C25—H25B	107.4
C5—C6—H6B	107.9	C25—C26—C33	114.4 (9)
H6A—C6—H6B	107.2	C25—C26—C27	109.6 (8)
C14—C7—C6	115.2 (9)	C33—C26—C27	110.7 (8)
C14—C7—C8	110.6 (9)	C25—C26—H26	107.3
C6—C7—C8	110.2 (9)	C33—C26—H26	107.3
C14—C7—H7	106.8	C27—C26—H26	107.3
C6—C7—H7	106.8	C28—C27—C26	116.3 (10)
C8—C7—H7	106.8	C28—C27—H27A	108.2
C9—C8—C7	114.1 (9)	C26—C27—H27A	108.2
C9—C8—H8A	108.7	C28—C27—H27B	108.2
C7—C8—H8A	108.7	C26—C27—H27B	108.2
C9—C8—H8B	108.7	H27A—C27—H27B	107.4
C7—C8—H8B	108.7	O4—C28—C29	117.4 (15)
H8A—C8—H8B	107.6	O4—C28—C27	117.9 (13)
O2—C9—C10	120.7 (11)	C29—C28—C27	124.6 (15)
O2—C9—C8	119.5 (11)	C30—C29—C28	123.0 (19)
C10—C9—C8	119.6 (11)	C30—C29—S4	112.8 (14)
C11—C10—C9	129.3 (11)	C28—C29—S4	124.1 (17)
C11—C10—S2	110.6 (10)	C29—C30—C31	108 (2)
C9—C10—S2	119.9 (10)	C29—C30—H30	126.1
C10—C11—C12	109.5 (12)	C31—C30—H30	126.1
C10—C11—H11	125.2	C32—C31—C30	118 (2)
C12—C11—H11	125.2	C32—C31—H31	120.9
C13—C12—C11	114.8 (14)	C30—C31—H31	120.9
C13—C12—H12	122.6	C31—C32—S4	107.4 (15)
C11—C12—H12	122.6	C31—C32—H32	126.3
C12—C13—S2	112.7 (11)	S4—C32—H32	126.3
C12—C13—H13	123.7	C34—C33—C38	118.0 (10)
S2—C13—H13	123.7	C34—C33—C26	123.2 (10)
C15—C14—C19	116.2 (11)	C38—C33—C26	118.8 (10)
C15—C14—C7	122.8 (11)	C33—C34—C35	122.4 (11)
C19—C14—C7	120.9 (11)	C33—C34—H34	118.8
C14—C15—C16	122.4 (12)	C35—C34—H34	118.8
C14—C15—H15	118.8	C34—C35—C36	119.1 (13)
C16—C15—H15	118.8	C34—C35—H35	120.5
C17—C16—C15	120.3 (14)	C36—C35—H35	120.5
C17—C16—H16	119.9	C37—C36—C35	119.9 (14)
C15—C16—H16	119.9	C37—C36—H36	120.1
C18—C17—C16	118.4 (14)	C35—C36—H36	120.1
C18—C17—H17	120.8	C36—C37—C38	123.3 (14)
C16—C17—H17	120.8	C36—C37—H37	118.3
C17—C18—C19	123.8 (13)	C38—C37—H37	118.3
C17—C18—H18	118.1	C37—C38—C33	117.0 (11)
C19—C18—H18	118.1	C37—C38—H38	121.5
C18—C19—C14	118.7 (12)	C33—C38—H38	121.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O4ⁱ	0.93	2.58	3.407 (16)	149
C1—H1···O2ⁱⁱ	0.93	2.54	3.279 (15)	137

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆O₂S₂
M_r	340.44
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	298
a, b, c (Å)	27.912 (3), 5.8607 (8), 20.841 (2)
V (Å³)	3409.2 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.26 × 0.17 × 0.09

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.922, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	13190, 5636, 2006
R_int	0.120
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.086, 0.192, 1.02
No. of reflections	5636
No. of parameters	415
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.45
Absolute structure	Flack (1983), 2565 Friedel pairs
Absolute structure parameter	0.18 (15)

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
C21—H21···O4ⁱ	0.93	2.58	3.407 (16)	148.9
C1—H1···O2ⁱⁱ	0.93	2.54	3.279 (15)	137.1

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

Acknowledgements

The authors acknowledge the support of the National Natural Science Foundation of Liaocheng University (grant No. X051040).

References

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