rac-2,2′-(Thiane-2,6-di­yl)bis­[1-(4-bromo­phen­yl)ethanone]

Liu, L.-Q.; Yang, J.-K.

doi:10.1107/S1600536811011792

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1047

doi:10.1107/S1600536811011792

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rac-2,2′-(Thiane-2,6-diyl)bis[1-(4-bromophenyl)ethanone]

Li-Qiang Liu ^a ^* and Jing-Kui Yang ^a

^aCollege of Chemistry and Chemical Engineering, Graduate University of Chinese, Academy of Sciences, Beijing, 100049, People's Republic of China
^*Correspondence e-mail: liqiangliu@163.com

(Received 17 March 2011; accepted 30 March 2011; online 7 April 2011)

In the title compound, C₂₁H₂₀Br₂O₂S, prepared by the reaction of 1,9-bis(4-bromophenyl)nona-2,7-diene-1,9-dione with sodium sulfide nonahydrate in acetonitrile, the six-membered thiopyran ring has a chair conformation while the H atoms ortho to the S atom adopt a cis configuration. The dihedral angle between the two benzene rings is 2.59 (8)°.

Related literature

For the synthesis of 1,9-bis(4-bromophenyl)nona-2,7-diene-1,9-dione, see: Yang, Cauble et al. (2004 ); Yang, Felton et al. (2004 ). For the synthesis of compounds containing sulfur, see: Knapp et al. (2002 ); Yao et al. (2003 ); Oliveira et al. (1999 ). For applications of natural products containing sulfur, see: Qi et al. (2004 ); Zhang & Zhang (2006 ); Barco et al. (2006 ).

Experimental

Crystal data

C₂₁H₂₀Br₂O₂S
M_r = 496.25
Triclinic, $[P \overline 1]$
a = 6.484 (4) Å
b = 12.970 (5) Å
c = 13.076 (4) Å
α = 71.14 (3)°
β = 79.45 (4)°
γ = 79.52 (4)°
V = 1014.1 (7) Å³
Z = 2
Mo Kα radiation
μ = 4.11 mm⁻¹
T = 295 K
0.40 × 0.30 × 0.20 mm

Data collection

Siemens P4 four-circle diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.381, T_max = 0.459
4549 measured reflections
3548 independent reflections
2220 reflections with I > 2σ(I)
R_int = 0.032
3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.112
S = 1.07
3548 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Data collection: XSCANS (Bruker, 1997 ); cell refinement: XSCANS; data reduction: XSCANS; 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/S1600536811011792/zs2103sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811011792/zs2103Isup2.hkl

checkCIF report

Comment top

The mothods for the synthesis of compounds containing sulfur have been described (Knapp et al., 2002; Yao et al., 2003; Oliveira et al. 1999). Natural products containing sulfur often have biological activity, so that the methods for their synthesis have received considerable attention among researchers. In this paper, we report the structure of the title compound C₂₁H₂₀Br₂O₂S (I), prepared by the reaction of 1,9-bis(4-bromophenyl)nona-2,7-diene-1,9-dione with sodium sulfide nonahydrate in acetonitrile. In the crystal, the six-membered thiopyran ring has a chair conformation with the H atoms ortho to the S (H9 and H13) adopting a cis configuration (Fig. 1). The dihedral angle between the benzene rings on the substituent chains is 2.59 (8)°.

Related literature top

For the synthesis of 1,9-bis(4-bromophenyl)nona-2,7-diene-1,9-dione, see: Yang, Cauble et al. (2004); Yang, Felton et al. (2004). For the synthesis of compounds containing sulfur, see: Knapp et al. (2002); Yao et al. (2003); Oliveira et al. (1999). For applications of natural products containing sulfur, see: Qi et al. (2004); Zhang & Zhang (2006); Barco et al. (2006).

Experimental top

The reaction mixture of 1,9-bis(4-bromophenyl)nona-2,7-diene-1,9-dione (100 mg, 0.20 mmol) with sodium sulfide nonahydrate (67 mg, 0.28 mmol) in 50 ml of acetonitrile was stirred for 11 days at room temperature, affording the title compound (20 mg; yield 32%). Colorless single crystals were obtained by slow evaporation of an ethyl acetate solution in air.

Computing details top

Data collection: XSCANS (Bruker, 1997); cell refinement: XSCANS (Bruker, 1997); data reduction: XSCANS (Bruker, 1997); 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 conformation of the title compound showing 35% probability displacement ellipsoids and the atom numbering scheme

rac-2,2'-(Thiane-2,6-diyl)bis[1-(4-bromophenyl)ethanone] top

Crystal data top

C₂₁H₂₀Br₂O₂S	Z = 2
M_r = 496.25	F(000) = 496
Triclinic, P1	D_x = 1.625 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.484 (4) Å	Cell parameters from 45 reflections
b = 12.970 (5) Å	θ = 5.6–12.4°
c = 13.076 (4) Å	µ = 4.11 mm⁻¹
α = 71.14 (3)°	T = 295 K
β = 79.45 (4)°	Prism, colorless
γ = 79.52 (4)°	0.40 × 0.30 × 0.20 mm
V = 1014.1 (7) Å³

Data collection top

Siemens P4 four-circle diffractometer	2220 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 25.1°, θ_min = 2.0°
ω scans	h = −1→7
Absorption correction: ψ scan (North et al., 1968)	k = −14→14
T_min = 0.381, T_max = 0.459	l = −15→15
4549 measured reflections	3 standard reflections every 97 reflections
3548 independent reflections	intensity decay: none

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.001P)² + 2.0P] where P = (F_o² + 2F_c²)/3
3548 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₂₁H₂₀Br₂O₂S	γ = 79.52 (4)°
M_r = 496.25	V = 1014.1 (7) Å³
Triclinic, P1	Z = 2
a = 6.484 (4) Å	Mo Kα radiation
b = 12.970 (5) Å	µ = 4.11 mm⁻¹
c = 13.076 (4) Å	T = 295 K
α = 71.14 (3)°	0.40 × 0.30 × 0.20 mm
β = 79.45 (4)°

Data collection top

Siemens P4 four-circle diffractometer	2220 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.032
T_min = 0.381, T_max = 0.459	3 standard reflections every 97 reflections
4549 measured reflections	intensity decay: none
3548 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.07	Δρ_max = 0.51 e Å⁻³
3548 reflections	Δρ_min = −0.41 e Å⁻³
235 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
Br1	0.47955 (9)	1.39832 (4)	0.65329 (4)	0.08336 (16)
Br2	0.87756 (10)	0.46636 (4)	−0.19734 (4)	0.09195 (19)
S1	0.35503 (17)	0.97967 (9)	0.19248 (8)	0.0594 (3)
O1	−0.0519 (5)	1.2370 (2)	0.3377 (2)	0.0755 (9)
O2	0.0963 (5)	0.8256 (2)	−0.0195 (2)	0.0740 (9)
C1	0.2190 (6)	1.2490 (3)	0.4300 (3)	0.0477 (10)
C2	0.4267 (6)	1.2193 (3)	0.4523 (3)	0.0596 (12)
H2A	0.5153	1.1687	0.4220	0.071*
C3	0.5051 (7)	1.2633 (3)	0.5185 (3)	0.0673 (13)
H3A	0.6453	1.2438	0.5316	0.081*
C4	0.3711 (6)	1.3365 (3)	0.5645 (3)	0.0559 (11)
C5	0.1643 (7)	1.3678 (3)	0.5447 (3)	0.0597 (12)
H5A	0.0760	1.4175	0.5764	0.072*
C6	0.0894 (7)	1.3245 (3)	0.4772 (3)	0.0568 (12)
H6A	−0.0499	1.3460	0.4630	0.068*
C7	0.1259 (7)	1.2030 (3)	0.3601 (3)	0.0543 (11)
C8	0.2614 (6)	1.1124 (3)	0.3196 (3)	0.0557 (11)
H8A	0.3138	1.0552	0.3815	0.067*
H8B	0.3829	1.1420	0.2711	0.067*
C9	0.1493 (6)	1.0605 (3)	0.2598 (3)	0.0494 (10)
H9A	0.0776	1.1190	0.2042	0.059*
C10	−0.0111 (6)	0.9885 (3)	0.3336 (3)	0.0601 (12)
H10A	−0.1162	1.0322	0.3709	0.072*
H10B	0.0599	0.9303	0.3884	0.072*
C11	−0.1229 (6)	0.9372 (3)	0.2727 (3)	0.0650 (13)
H11A	−0.2286	0.8956	0.3238	0.078*
H11B	−0.1954	0.9953	0.2184	0.078*
C12	0.0287 (6)	0.8618 (3)	0.2168 (3)	0.0588 (12)
H12A	−0.0519	0.8293	0.1826	0.071*
H12B	0.0979	0.8027	0.2717	0.071*
C13	0.1970 (6)	0.9190 (3)	0.1311 (3)	0.0517 (11)
H13A	0.1284	0.9771	0.0739	0.062*
C14	0.3569 (6)	0.8426 (3)	0.0794 (3)	0.0561 (12)
H14A	0.4755	0.8815	0.0400	0.067*
H14B	0.4100	0.7805	0.1374	0.067*
C15	0.2757 (7)	0.7987 (3)	0.0020 (3)	0.0543 (12)
C16	0.4289 (6)	0.7209 (3)	−0.0478 (3)	0.0530 (11)
C17	0.3596 (7)	0.6792 (3)	−0.1196 (3)	0.0645 (13)
H17A	0.2225	0.7017	−0.1372	0.077*
C18	0.4938 (7)	0.6047 (3)	−0.1650 (3)	0.0667 (13)
H18A	0.4479	0.5780	−0.2137	0.080*
C19	0.6922 (7)	0.5709 (3)	−0.1379 (3)	0.0646 (13)
C20	0.7680 (8)	0.6127 (3)	−0.0700 (3)	0.0719 (14)
H20A	0.9069	0.5912	−0.0550	0.086*
C21	0.6352 (7)	0.6872 (3)	−0.0241 (3)	0.0657 (13)
H21A	0.6846	0.7148	0.0229	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1169 (4)	0.0718 (3)	0.0768 (3)	−0.0107 (3)	−0.0346 (3)	−0.0323 (2)
Br2	0.1217 (5)	0.0730 (3)	0.0745 (3)	0.0071 (3)	0.0042 (3)	−0.0334 (2)
S1	0.0517 (6)	0.0715 (6)	0.0667 (6)	−0.0140 (5)	−0.0006 (5)	−0.0374 (5)
O1	0.0630 (18)	0.0824 (17)	0.0972 (18)	0.0060 (16)	−0.0260 (15)	−0.0490 (15)
O2	0.0769 (19)	0.0751 (17)	0.0793 (17)	0.0154 (16)	−0.0348 (15)	−0.0364 (14)
C1	0.051 (2)	0.0488 (19)	0.0465 (19)	−0.0129 (18)	−0.0055 (17)	−0.0160 (16)
C2	0.049 (2)	0.067 (2)	0.067 (2)	−0.004 (2)	0.000 (2)	−0.0335 (19)
C3	0.063 (3)	0.075 (3)	0.074 (3)	−0.010 (2)	−0.014 (2)	−0.033 (2)
C4	0.070 (3)	0.053 (2)	0.050 (2)	−0.016 (2)	−0.013 (2)	−0.0154 (17)
C5	0.076 (3)	0.050 (2)	0.052 (2)	0.003 (2)	−0.011 (2)	−0.0193 (17)
C6	0.058 (3)	0.055 (2)	0.056 (2)	−0.001 (2)	−0.012 (2)	−0.0159 (18)
C7	0.055 (2)	0.055 (2)	0.053 (2)	−0.007 (2)	−0.0016 (19)	−0.0191 (17)
C8	0.056 (2)	0.060 (2)	0.058 (2)	−0.013 (2)	−0.0022 (19)	−0.0272 (17)
C9	0.043 (2)	0.057 (2)	0.0519 (19)	−0.0110 (18)	−0.0026 (17)	−0.0212 (17)
C10	0.056 (2)	0.064 (2)	0.061 (2)	−0.012 (2)	0.004 (2)	−0.0246 (19)
C11	0.052 (2)	0.070 (3)	0.072 (3)	−0.017 (2)	0.000 (2)	−0.019 (2)
C12	0.063 (3)	0.058 (2)	0.059 (2)	−0.024 (2)	−0.005 (2)	−0.0159 (19)
C13	0.057 (2)	0.051 (2)	0.0507 (19)	−0.0033 (19)	−0.0162 (18)	−0.0179 (16)
C14	0.063 (3)	0.055 (2)	0.055 (2)	−0.010 (2)	−0.011 (2)	−0.0196 (18)
C15	0.072 (3)	0.0383 (19)	0.052 (2)	−0.006 (2)	−0.013 (2)	−0.0118 (16)
C16	0.066 (3)	0.0443 (19)	0.051 (2)	−0.0110 (19)	−0.0120 (19)	−0.0125 (17)
C17	0.074 (3)	0.065 (2)	0.060 (2)	−0.010 (2)	−0.016 (2)	−0.0232 (19)
C18	0.080 (3)	0.068 (2)	0.064 (2)	−0.016 (2)	−0.011 (2)	−0.0317 (19)
C19	0.083 (3)	0.054 (2)	0.053 (2)	−0.007 (2)	0.001 (2)	−0.0183 (19)
C20	0.078 (3)	0.063 (2)	0.074 (3)	0.004 (2)	−0.013 (2)	−0.026 (2)
C21	0.075 (3)	0.068 (2)	0.061 (2)	−0.007 (2)	−0.015 (2)	−0.0262 (19)

Geometric parameters (Å, º) top

Br1—C4	1.895 (4)	C10—H10A	0.9700
Br2—C19	1.906 (4)	C10—H10B	0.9700
S1—C9	1.819 (4)	C11—C12	1.518 (6)
S1—C13	1.820 (4)	C11—H11A	0.9700
O1—C7	1.210 (5)	C11—H11B	0.9700
O2—C15	1.209 (5)	C12—C13	1.518 (5)
C1—C2	1.389 (5)	C12—H12A	0.9700
C1—C6	1.395 (5)	C12—H12B	0.9700
C1—C7	1.497 (6)	C13—C14	1.523 (5)
C2—C3	1.386 (6)	C13—H13A	0.9800
C2—H2A	0.9300	C14—C15	1.517 (6)
C3—C4	1.377 (6)	C14—H14A	0.9700
C3—H3A	0.9300	C14—H14B	0.9700
C4—C5	1.375 (6)	C15—C16	1.500 (5)
C5—C6	1.381 (6)	C16—C21	1.389 (6)
C5—H5A	0.9300	C16—C17	1.396 (6)
C6—H6A	0.9300	C17—C18	1.385 (6)
C7—C8	1.513 (5)	C17—H17A	0.9300
C8—C9	1.523 (6)	C18—C19	1.354 (6)
C8—H8A	0.9700	C18—H18A	0.9300
C8—H8B	0.9700	C19—C20	1.376 (7)
C9—C10	1.512 (5)	C20—C21	1.385 (6)
C9—H9A	0.9800	C20—H20A	0.9300
C10—C11	1.528 (6)	C21—H21A	0.9300

C9—S1—C13	101.01 (18)	C12—C11—H11B	109.1
C2—C1—C6	117.9 (4)	C10—C11—H11B	109.1
C2—C1—C7	123.7 (4)	H11A—C11—H11B	107.8
C6—C1—C7	118.4 (4)	C11—C12—C13	114.0 (3)
C3—C2—C1	121.6 (4)	C11—C12—H12A	108.8
C3—C2—H2A	119.2	C13—C12—H12A	108.8
C1—C2—H2A	119.2	C11—C12—H12B	108.8
C4—C3—C2	118.6 (4)	C13—C12—H12B	108.8
C4—C3—H3A	120.7	H12A—C12—H12B	107.7
C2—C3—H3A	120.7	C12—C13—C14	114.1 (3)
C5—C4—C3	121.6 (4)	C12—C13—S1	110.2 (3)
C5—C4—Br1	119.8 (3)	C14—C13—S1	104.6 (3)
C3—C4—Br1	118.6 (3)	C12—C13—H13A	109.2
C4—C5—C6	119.1 (4)	C14—C13—H13A	109.2
C4—C5—H5A	120.5	S1—C13—H13A	109.2
C6—C5—H5A	120.5	C15—C14—C13	116.0 (3)
C5—C6—C1	121.2 (4)	C15—C14—H14A	108.3
C5—C6—H6A	119.4	C13—C14—H14A	108.3
C1—C6—H6A	119.4	C15—C14—H14B	108.3
O1—C7—C1	120.8 (4)	C13—C14—H14B	108.3
O1—C7—C8	121.6 (4)	H14A—C14—H14B	107.4
C1—C7—C8	117.6 (3)	O2—C15—C16	121.3 (4)
C7—C8—C9	114.9 (3)	O2—C15—C14	121.8 (4)
C7—C8—H8A	108.5	C16—C15—C14	117.0 (4)
C9—C8—H8A	108.5	C21—C16—C17	118.6 (4)
C7—C8—H8B	108.5	C21—C16—C15	122.9 (4)
C9—C8—H8B	108.5	C17—C16—C15	118.5 (4)
H8A—C8—H8B	107.5	C18—C17—C16	120.4 (4)
C10—C9—C8	113.7 (3)	C18—C17—H17A	119.8
C10—C9—S1	110.1 (3)	C16—C17—H17A	119.8
C8—C9—S1	106.4 (3)	C19—C18—C17	119.6 (4)
C10—C9—H9A	108.8	C19—C18—H18A	120.2
C8—C9—H9A	108.8	C17—C18—H18A	120.2
S1—C9—H9A	108.8	C18—C19—C20	121.5 (4)
C9—C10—C11	113.2 (3)	C18—C19—Br2	120.3 (4)
C9—C10—H10A	108.9	C20—C19—Br2	118.1 (4)
C11—C10—H10A	108.9	C19—C20—C21	119.3 (5)
C9—C10—H10B	108.9	C19—C20—H20A	120.4
C11—C10—H10B	108.9	C21—C20—H20A	120.4
H10A—C10—H10B	107.7	C20—C21—C16	120.5 (4)
C12—C11—C10	112.6 (3)	C20—C21—H21A	119.8
C12—C11—H11A	109.1	C16—C21—H21A	119.8
C10—C11—H11A	109.1

Experimental details

Crystal data
Chemical formula	C₂₁H₂₀Br₂O₂S
M_r	496.25
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	6.484 (4), 12.970 (5), 13.076 (4)
α, β, γ (°)	71.14 (3), 79.45 (4), 79.52 (4)
V (Å³)	1014.1 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.11
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Siemens P4 four-circle diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.381, 0.459
No. of measured, independent and observed [I > 2σ(I)] reflections	4549, 3548, 2220
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.112, 1.07
No. of reflections	3548
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.41

Computer programs: XSCANS (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This research was supported by the NSFC·SRF for ROCS, SEM, the Present Fund of GUCAS and the Opening Fund of the Laboratory of Organic Solids, CAS, China

References

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