rac-2,2'-(Thiane-2,6-di-yl)bis-[1-(4-bromo-phen-yl)ethanone].

In the title compound, C(21)H(20)Br(2)O(2)S, prepared by the reaction of 1,9-bis-(4-bromo-phen-yl)nona-2,7-diene-1,9-dione with sodium sulfide nona-hydrate in acetonitrile, the six-membered thio-pyran 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 = 496.25

Triclinic,

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[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.112

S = 1.07

3548 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011792/zs2103sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Enhanced figure: interactive version of Fig. 1

C21H20Br2O2S	Z = 2
Mr = 496.25	F(000) = 496
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.001P)2 + 2.0P] where P = (Fo2 + 2Fc2)/3
3548 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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