Ethyl 4-(3-bromo-2-thien­yl)-2-oxo-6-phenyl­cyclo­hex-3-ene-1-carboxyl­ate

Fischer, A.; Yathirajan, H.S.; Ashalatha, B.V.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536808002717

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o560

doi:10.1107/S1600536808002717

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Ethyl 4-(3-bromo-2-thienyl)-2-oxo-6-phenylcyclohex-3-ene-1-carboxylate

Andreas Fischer,^a ^* H. S. Yathirajan,^b B. V. Ashalatha,^c B. Narayana ^c and B. K. Sarojini ^d

^aInorganic Chemistry, School of Chemical Science and Engineering, Royal Institute of Technology (KTH), 100 44 Stockholm, Sweden, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, ^cDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^dDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: afischer@kth.se

(Received 4 December 2007; accepted 24 January 2008; online 6 February 2008)

The title compound, C₁₉H₁₇BrO₃S, crystallizes with two molecules in the asymmetric unit. The methyl group of one molecule is disordered approximately equally over two positions. The dihedral angles between the thiophene and phenyl groups are 68.5 (2) and 67.5 (2)° in the two molecules.

Related literature

For related structures, see Fischer et al. (2007a ,b ). For related literature, see: House (1972 ); Tabba et al. (1995 ); Dimmock et al. (1999 ).

Experimental

Crystal data

C₁₉H₁₇BrO₃S
M_r = 405.31
Triclinic, $[P \overline 1]$
a = 8.8925 (8) Å
b = 11.713 (2) Å
c = 16.853 (2) Å
α = 94.317 (11)°
β = 98.436 (10)°
γ = 90.235 (13)°
V = 1731.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.50 mm⁻¹
T = 130 K
0.30 × 0.17 × 0.05 mm

Data collection

Bruker Nonius KappaCCD diffractometer
Absorption correction: numerical (HABITUS; Herrendorf & Bärnighausen, 1997 ) T_min = 0.638, T_max = 0.843
40436 measured reflections
7898 independent reflections
6074 reflections with I > 2σ(I)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.089
S = 1.04
7898 reflections
438 parameters
H-atom parameters constrained
Δρ_max = 0.84 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Data collection: COLLECT (Nonius, 1999 ); cell refinement: DIRAX (Duisenberg, 1992 ); data reduction: EVALCCD (Duisenberg et al., 2003 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2007 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002717/pv2059sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808002717/pv2059Isup2.hkl

checkCIF report

Comment top

Chalcones and the corresponding heterocyclic analogs are valuable intermediates in organic synthesis and exhibit a multitude of biological activities (Dimmock et al., 1999). An important feature of chalcones and their heteroanalogs is the ability to act as activated unsaturated systems in conjugated addition reactions of carbanions in the presence of basic catalysts (House, 1972). This type of reaction may be exploited with the goal of obtaining highly functionalized cyclohexene derivatives (Tabba et al., 1995). In view of the importance of these derivatives and continuing our efforts in this field (Fischer et al., 2007a; 2007b), a new derivative, the title compound, (I), has been prepared and its crystal structure is reported in this paper.

The structure of (I) contains two molecules in an asymmetric unit (Figs. 1 and 2). A methyl C-atom of methoxy group in the molecule 1, presented in Fig. 1 is disordered over two sites C19 and C19'. The geometry in the two molecules is unexceptional. The crystal packing is stabilized by van der Waals forces. The dihedral angles between the thiophene groups and phenyl groups in the two molecules are 68.5 (2) and 67.5 (2)°.

Related literature top

For related structures, see Fischer et al. (2007a,b). For related literature, see: House (1972); Tabba et al. (1995); Dimmock et al. (1999).

Experimental top

(2E)-1-(3-Bromo-2-thienyl)-3-phenylprop-2-en-1-one (1.5 g, 5 mmol) and ethyl acetoacetate (0.65 g, 5 mmol) were refluxed for 2 hr in 10–15 ml e thanol in the presence of 0.8 ml 10% NaOH. The reaction mixture was cooled to room temperature and the reaction mass was filtered and recrystallized using methanol. Crystals were grown from acetone (m.p. 399–400 K).

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2007); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

	Fig. 1. The structure of molecule 1 in the asymmetric unit; displacement ellipsoids have been plotted at the 50% probability level. Only one of the conformational isomers is shown.
	Fig. 2. The structure of molecule 2 in the asymmetric unit; displacement ellipsoids have been plotted at the 50% probability level.

Ethyl 4-(3-bromo-2-thienyl)-2-oxo-6-phenylcyclohex-3-ene-1-carboxylate top

Crystal data top

C₁₉H₁₇BrO₃S	Z = 4
M_r = 405.32	F(000) = 824
Triclinic, P1	D_x = 1.555 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8925 (8) Å	Cell parameters from 44 reflections
b = 11.713 (2) Å	θ = 6.3–19.4°
c = 16.853 (2) Å	µ = 2.50 mm⁻¹
α = 94.317 (11)°	T = 130 K
β = 98.436 (10)°	Plate, colourless
γ = 90.235 (13)°	0.30 × 0.17 × 0.05 mm
V = 1731.3 (4) Å³

Data collection top

Bruker Nonius KappaCCD diffractometer	6074 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.073
ϕ and ω scans	θ_max = 27.5°, θ_min = 4.5°
Absorption correction: numerical (HABITUS; Herrendorf & Bärnighausen, 1997)	h = −11→11
T_min = 0.638, T_max = 0.843	k = −15→15
40436 measured reflections	l = −21→21
7898 independent reflections

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.090	w = 1/[σ²(F_o²) + (0.0305P)² + 2.19P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
7898 reflections	Δρ_max = 0.84 e Å⁻³
438 parameters	Δρ_min = −0.54 e Å⁻³
0 restraints

Crystal data top

C₁₉H₁₇BrO₃S	γ = 90.235 (13)°
M_r = 405.32	V = 1731.3 (4) Å³
Triclinic, P1	Z = 4
a = 8.8925 (8) Å	Mo Kα radiation
b = 11.713 (2) Å	µ = 2.50 mm⁻¹
c = 16.853 (2) Å	T = 130 K
α = 94.317 (11)°	0.30 × 0.17 × 0.05 mm
β = 98.436 (10)°

Data collection top

Bruker Nonius KappaCCD diffractometer	7898 independent reflections
Absorption correction: numerical (HABITUS; Herrendorf & Bärnighausen, 1997)	6074 reflections with I > 2σ(I)
T_min = 0.638, T_max = 0.843	R_int = 0.073
40436 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.04	Δρ_max = 0.84 e Å⁻³
7898 reflections	Δρ_min = −0.54 e Å⁻³
438 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	Occ. (<1)
Br1	0.99977 (4)	0.72535 (2)	0.421420 (19)	0.03009 (9)
S1	0.66855 (8)	0.46246 (6)	0.45787 (4)	0.02458 (16)
O1	1.1493 (2)	0.73022 (18)	0.71856 (13)	0.0311 (5)
O2	1.1039 (3)	0.52832 (19)	0.83761 (14)	0.0368 (5)
O3	1.0313 (3)	0.69989 (19)	0.88526 (14)	0.0408 (6)
C1	0.6729 (3)	0.4794 (3)	0.35854 (18)	0.0263 (6)
C2	0.7753 (3)	0.5611 (2)	0.34871 (18)	0.0236 (6)
C3	0.8510 (3)	0.6105 (2)	0.42277 (17)	0.0212 (6)
C4	0.8073 (3)	0.5679 (2)	0.49033 (17)	0.0203 (6)
C5	0.8539 (3)	0.5935 (2)	0.57634 (17)	0.0197 (6)
C6	0.9826 (3)	0.6524 (2)	0.60774 (18)	0.0214 (6)
C7	1.0306 (3)	0.6775 (2)	0.69339 (18)	0.0225 (6)
C8	0.9305 (3)	0.6373 (2)	0.75173 (17)	0.0213 (6)
C9	0.8343 (3)	0.5321 (2)	0.71617 (17)	0.0208 (6)
C10	0.7514 (3)	0.5522 (2)	0.63266 (16)	0.0206 (6)
C11	0.7227 (3)	0.4959 (2)	0.76997 (17)	0.0209 (6)
C12	0.7020 (3)	0.3799 (2)	0.77736 (19)	0.0285 (7)
C13	0.5923 (4)	0.3416 (3)	0.8206 (2)	0.0361 (8)
C14	0.5035 (4)	0.4191 (3)	0.8572 (2)	0.0374 (8)
C15	0.5246 (4)	0.5351 (3)	0.8508 (2)	0.0350 (7)
C16	0.6338 (3)	0.5729 (2)	0.80828 (18)	0.0263 (6)
C17	1.0313 (3)	0.6139 (2)	0.82876 (18)	0.0251 (6)
C18	1.1320 (5)	0.6868 (4)	0.9614 (2)	0.0555 (11)
C19	1.2037 (10)	0.8086 (8)	0.9813 (5)	0.0623 (17)	0.513 (6)
C19'	1.0611 (10)	0.5946 (9)	1.0106 (5)	0.0623 (17)	0.487 (6)
Br2	0.50916 (3)	0.75741 (2)	0.418423 (18)	0.02812 (9)
S2	0.16982 (8)	1.01911 (6)	0.45701 (4)	0.02397 (16)
O4	0.6550 (2)	0.81534 (18)	0.71690 (13)	0.0306 (5)
O5	0.6026 (2)	1.03913 (17)	0.84067 (13)	0.0324 (5)
O6	0.5409 (2)	0.86917 (17)	0.88122 (12)	0.0286 (5)
C20	0.1748 (3)	0.9822 (3)	0.35764 (18)	0.0261 (6)
C21	0.2799 (3)	0.9014 (2)	0.34699 (18)	0.0241 (6)
C22	0.3574 (3)	0.8687 (2)	0.42091 (17)	0.0201 (6)
C23	0.3116 (3)	0.9236 (2)	0.48873 (17)	0.0195 (6)
C24	0.3592 (3)	0.9170 (2)	0.57463 (17)	0.0186 (6)
C25	0.4871 (3)	0.8656 (2)	0.60608 (17)	0.0215 (6)
C26	0.5353 (3)	0.8602 (2)	0.69166 (18)	0.0217 (6)
C27	0.4338 (3)	0.9107 (2)	0.75024 (16)	0.0190 (6)
C28	0.3404 (3)	1.0092 (2)	0.71490 (16)	0.0191 (6)
C29	0.2568 (3)	0.9709 (2)	0.63110 (16)	0.0202 (6)
C30	0.2268 (3)	1.0582 (2)	0.76721 (17)	0.0218 (6)
C31	0.1404 (3)	0.9897 (3)	0.80725 (19)	0.0290 (7)
C32	0.0259 (4)	1.0375 (3)	0.8464 (2)	0.0387 (8)
C33	−0.0024 (4)	1.1527 (3)	0.8463 (2)	0.0412 (9)
C34	0.0858 (4)	1.2217 (3)	0.8088 (2)	0.0396 (8)
C35	0.1999 (4)	1.1751 (3)	0.76958 (18)	0.0293 (7)
C36	0.5346 (3)	0.9491 (2)	0.82818 (18)	0.0225 (6)
C37	0.6474 (4)	0.8921 (3)	0.9551 (2)	0.0422 (9)
C38	0.6280 (6)	0.7991 (4)	1.0081 (3)	0.0655 (13)
H1	0.6111	0.4369	0.3155	0.032*
H2	0.7940	0.5825	0.2977	0.028*
H6	1.0451	0.6788	0.5716	0.026*
H8	0.8608	0.7005	0.7640	0.026*
H9	0.9050	0.4673	0.7097	0.025*
H10A	0.7006	0.4800	0.6083	0.025*
H10B	0.6718	0.6095	0.6383	0.025*
H12	0.7632	0.3260	0.7526	0.034*
H13	0.5787	0.2620	0.8250	0.043*
H14	0.4284	0.3933	0.8865	0.045*
H15	0.4635	0.5888	0.8758	0.042*
H16	0.6484	0.6527	0.8052	0.032*
H18A	1.2102	0.6289	0.9544	0.067*	0.513 (6)
H18B	1.0740	0.6651	1.0040	0.067*	0.513 (6)
H19A	1.2746	0.8103	1.0317	0.093*	0.513 (6)
H19B	1.1235	0.8640	0.9872	0.093*	0.513 (6)
H19C	1.2581	0.8283	0.9376	0.093*	0.513 (6)
H18C	1.1448	0.7611	0.9939	0.067*	0.487 (6)
H18D	1.2330	0.6618	0.9500	0.067*	0.487 (6)
H19D	1.1287	0.5856	1.0610	0.093*	0.487 (6)
H19E	1.0488	0.5211	0.9784	0.093*	0.487 (6)
H19F	0.9619	0.6203	1.0226	0.093*	0.487 (6)
H20	0.1117	1.0143	0.3149	0.031*
H21	0.2992	0.8704	0.2958	0.029*
H25	0.5490	0.8310	0.5700	0.026*
H27	0.3627	0.8495	0.7611	0.023*
H28	0.4128	1.0723	0.7087	0.023*
H29A	0.1761	0.9149	0.6366	0.024*
H29B	0.2074	1.0379	0.6068	0.024*
H31	0.1593	0.9102	0.8080	0.035*
H32	−0.0334	0.9900	0.8735	0.046*
H33	−0.0823	1.1843	0.8720	0.049*
H34	0.0684	1.3016	0.8097	0.048*
H35	0.2606	1.2236	0.7440	0.035*
H37A	0.6266	0.9671	0.9820	0.051*
H37B	0.7527	0.8938	0.9429	0.051*
H38A	0.5228	0.7968	1.0185	0.098*
H38B	0.6961	0.8135	1.0592	0.098*
H38C	0.6524	0.7257	0.9816	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03887 (18)	0.02276 (15)	0.02951 (18)	−0.00756 (12)	0.00681 (13)	0.00493 (12)
S1	0.0186 (3)	0.0318 (4)	0.0222 (4)	−0.0066 (3)	0.0026 (3)	−0.0035 (3)
O1	0.0262 (11)	0.0335 (12)	0.0313 (12)	−0.0141 (9)	0.0019 (9)	−0.0072 (9)
O2	0.0390 (13)	0.0326 (12)	0.0364 (14)	0.0065 (10)	−0.0033 (10)	0.0034 (10)
O3	0.0517 (14)	0.0370 (13)	0.0294 (13)	−0.0003 (11)	−0.0008 (11)	−0.0113 (10)
C1	0.0234 (15)	0.0328 (16)	0.0213 (15)	0.0020 (12)	0.0015 (12)	−0.0043 (12)
C2	0.0249 (14)	0.0255 (14)	0.0206 (15)	0.0069 (12)	0.0031 (12)	0.0042 (12)
C3	0.0198 (13)	0.0177 (13)	0.0267 (16)	0.0039 (11)	0.0057 (11)	0.0007 (11)
C4	0.0153 (13)	0.0179 (13)	0.0273 (16)	0.0020 (10)	0.0036 (11)	−0.0022 (11)
C5	0.0190 (13)	0.0163 (13)	0.0241 (15)	0.0027 (10)	0.0046 (11)	0.0010 (11)
C6	0.0168 (13)	0.0217 (14)	0.0263 (16)	−0.0031 (11)	0.0059 (11)	0.0003 (11)
C7	0.0200 (14)	0.0172 (13)	0.0297 (16)	−0.0018 (11)	0.0040 (12)	−0.0026 (11)
C8	0.0195 (13)	0.0202 (13)	0.0231 (15)	−0.0019 (11)	0.0009 (11)	−0.0009 (11)
C9	0.0229 (14)	0.0175 (13)	0.0214 (15)	−0.0033 (11)	0.0027 (11)	−0.0020 (11)
C10	0.0184 (13)	0.0236 (14)	0.0191 (15)	−0.0044 (11)	0.0020 (11)	−0.0011 (11)
C11	0.0217 (14)	0.0219 (14)	0.0180 (14)	−0.0040 (11)	−0.0007 (11)	0.0012 (11)
C12	0.0357 (17)	0.0211 (14)	0.0285 (17)	−0.0019 (13)	0.0047 (13)	0.0012 (12)
C13	0.048 (2)	0.0258 (16)	0.0357 (19)	−0.0106 (15)	0.0062 (16)	0.0073 (14)
C14	0.0434 (19)	0.0421 (19)	0.0288 (18)	−0.0178 (16)	0.0123 (15)	0.0051 (15)
C15	0.0362 (18)	0.0385 (18)	0.0319 (19)	−0.0043 (15)	0.0127 (14)	−0.0016 (14)
C16	0.0298 (16)	0.0204 (14)	0.0287 (17)	−0.0031 (12)	0.0044 (13)	0.0023 (12)
C17	0.0242 (15)	0.0249 (15)	0.0253 (16)	−0.0048 (12)	0.0034 (12)	−0.0022 (12)
C18	0.061 (3)	0.070 (3)	0.028 (2)	−0.002 (2)	−0.0077 (18)	−0.0136 (19)
C19	0.061 (4)	0.093 (5)	0.031 (3)	−0.031 (3)	−0.003 (3)	0.013 (3)
C18'	0.061 (3)	0.070 (3)	0.028 (2)	−0.002 (2)	−0.0077 (18)	−0.0136 (19)
C19'	0.061 (4)	0.093 (5)	0.031 (3)	−0.031 (3)	−0.003 (3)	0.013 (3)
Br2	0.03497 (17)	0.02113 (15)	0.02934 (17)	0.00523 (12)	0.00939 (13)	−0.00052 (12)
S2	0.0190 (3)	0.0310 (4)	0.0221 (4)	0.0037 (3)	0.0031 (3)	0.0031 (3)
O4	0.0284 (11)	0.0332 (11)	0.0313 (12)	0.0125 (9)	0.0048 (9)	0.0088 (9)
O5	0.0354 (12)	0.0249 (11)	0.0342 (13)	−0.0089 (9)	−0.0044 (10)	0.0040 (9)
O6	0.0309 (11)	0.0289 (11)	0.0246 (12)	−0.0072 (9)	−0.0035 (9)	0.0083 (9)
C20	0.0233 (15)	0.0327 (16)	0.0220 (16)	−0.0025 (12)	0.0013 (12)	0.0041 (12)
C21	0.0248 (14)	0.0259 (14)	0.0216 (15)	−0.0086 (12)	0.0060 (12)	−0.0024 (12)
C22	0.0169 (13)	0.0174 (13)	0.0259 (16)	−0.0049 (10)	0.0043 (11)	−0.0005 (11)
C23	0.0162 (13)	0.0165 (13)	0.0263 (15)	−0.0050 (10)	0.0049 (11)	0.0023 (11)
C24	0.0186 (13)	0.0147 (12)	0.0232 (15)	−0.0047 (10)	0.0063 (11)	0.0004 (11)
C25	0.0214 (14)	0.0184 (13)	0.0262 (16)	−0.0001 (11)	0.0089 (11)	0.0010 (11)
C26	0.0199 (14)	0.0160 (13)	0.0301 (16)	−0.0012 (11)	0.0049 (12)	0.0050 (11)
C27	0.0201 (13)	0.0163 (13)	0.0211 (15)	−0.0036 (10)	0.0034 (11)	0.0036 (11)
C28	0.0183 (13)	0.0182 (13)	0.0204 (15)	−0.0007 (10)	0.0022 (11)	0.0007 (11)
C29	0.0187 (13)	0.0214 (13)	0.0215 (15)	0.0018 (11)	0.0042 (11)	0.0052 (11)
C30	0.0195 (13)	0.0277 (14)	0.0161 (14)	0.0044 (11)	−0.0021 (11)	−0.0022 (11)
C31	0.0287 (16)	0.0287 (16)	0.0294 (17)	−0.0021 (13)	0.0065 (13)	−0.0024 (13)
C32	0.0329 (18)	0.056 (2)	0.0289 (19)	−0.0015 (16)	0.0122 (14)	−0.0029 (16)
C33	0.0376 (19)	0.059 (2)	0.0263 (18)	0.0207 (17)	0.0074 (15)	−0.0065 (16)
C34	0.054 (2)	0.0369 (18)	0.0260 (18)	0.0212 (16)	0.0003 (16)	−0.0033 (14)
C35	0.0348 (17)	0.0294 (16)	0.0230 (16)	0.0075 (13)	0.0020 (13)	0.0019 (13)
C36	0.0186 (13)	0.0240 (15)	0.0252 (16)	0.0005 (11)	0.0033 (11)	0.0033 (12)
C37	0.048 (2)	0.044 (2)	0.0289 (19)	−0.0130 (16)	−0.0134 (15)	0.0074 (15)
C38	0.095 (3)	0.053 (2)	0.040 (2)	−0.020 (2)	−0.027 (2)	0.0200 (19)

Geometric parameters (Å, º) top

Br1—C3	1.888 (3)	C30—C31	1.385 (4)
S1—C1	1.706 (3)	C30—C35	1.392 (4)
S1—C4	1.743 (3)	C31—C32	1.393 (4)
O1—C7	1.225 (3)	C32—C33	1.376 (5)
O2—C17	1.201 (3)	C33—C34	1.374 (5)
O3—C17	1.333 (4)	C34—C35	1.386 (4)
O3—C18	1.474 (4)	C37—C38	1.486 (5)
C1—C2	1.355 (4)	C1—H1	0.9500
C2—C3	1.410 (4)	C2—H2	0.9500
C3—C4	1.382 (4)	C6—H6	0.9500
C4—C5	1.455 (4)	C8—H8	1.0000
C5—C6	1.353 (4)	C9—H9	1.0000
C5—C10	1.512 (4)	C10—H10A	0.9900
C6—C7	1.451 (4)	C10—H10B	0.9900
C7—C8	1.519 (4)	C12—H12	0.9500
C8—C17	1.511 (4)	C13—H13	0.9500
C8—C9	1.530 (4)	C14—H14	0.9500
C9—C11	1.520 (4)	C15—H15	0.9500
C9—C10	1.526 (4)	C16—H16	0.9500
C11—C12	1.389 (4)	C18—H18A	0.9900
C11—C16	1.390 (4)	C18—H18B	0.9900
C12—C13	1.394 (4)	C19—H19A	0.9800
C13—C14	1.378 (5)	C19—H19B	0.9800
C14—C15	1.386 (5)	C19—H19C	0.9800
C15—C16	1.380 (4)	C19'—H19D	0.9800
C18—C19	1.554 (9)	C19'—H19E	0.9800
Br2—C22	1.883 (3)	C19'—H19F	0.9800
S2—C20	1.704 (3)	C20—H20	0.9500
S2—C23	1.741 (3)	C21—H21	0.9500
O4—C26	1.223 (3)	C25—H25	0.9500
O5—C36	1.203 (3)	C27—H27	1.0000
O6—C36	1.339 (3)	C28—H28	1.0000
O6—C37	1.457 (4)	C29—H29A	0.9900
C20—C21	1.358 (4)	C29—H29B	0.9900
C21—C22	1.414 (4)	C31—H31	0.9500
C22—C23	1.384 (4)	C32—H32	0.9500
C23—C24	1.455 (4)	C33—H33	0.9500
C24—C25	1.351 (4)	C34—H34	0.9500
C24—C29	1.520 (4)	C35—H35	0.9500
C25—C26	1.449 (4)	C37—H37A	0.9900
C26—C27	1.524 (4)	C37—H37B	0.9900
C27—C36	1.515 (4)	C38—H38A	0.9800
C27—C28	1.534 (4)	C38—H38B	0.9800
C28—C30	1.525 (4)	C38—H38C	0.9800
C28—C29	1.530 (4)

C1—S1—C4	93.37 (14)	C5—C6—H6	118.1
C17—O3—C18	115.6 (3)	C7—C6—H6	118.1
C2—C1—S1	111.6 (2)	C17—C8—H8	108.4
C1—C2—C3	112.3 (3)	C7—C8—H8	108.4
C4—C3—C2	115.1 (2)	C9—C8—H8	108.4
C4—C3—Br1	126.4 (2)	C11—C9—H9	107.5
C2—C3—Br1	118.5 (2)	C10—C9—H9	107.5
C3—C4—C5	133.4 (2)	C8—C9—H9	107.5
C3—C4—S1	107.7 (2)	C5—C10—H10A	108.8
C5—C4—S1	118.9 (2)	C9—C10—H10A	108.8
C6—C5—C4	123.3 (3)	C5—C10—H10B	108.8
C6—C5—C10	119.0 (3)	C9—C10—H10B	108.8
C4—C5—C10	117.7 (2)	H10A—C10—H10B	107.7
C5—C6—C7	123.8 (3)	C11—C12—H12	119.6
O1—C7—C6	121.0 (3)	C13—C12—H12	119.6
O1—C7—C8	120.3 (3)	C14—C13—H13	120.0
C6—C7—C8	118.6 (2)	C12—C13—H13	120.0
C17—C8—C7	108.0 (2)	C13—C14—H14	120.2
C17—C8—C9	111.7 (2)	C15—C14—H14	120.2
C7—C8—C9	111.9 (2)	C16—C15—H15	119.8
C11—C9—C10	110.4 (2)	C14—C15—H15	119.8
C11—C9—C8	113.2 (2)	C15—C16—H16	119.6
C10—C9—C8	110.5 (2)	C11—C16—H16	119.6
C5—C10—C9	113.8 (2)	O3—C18—H18A	111.4
C12—C11—C16	118.4 (3)	C19—C18—H18A	111.4
C12—C11—C9	118.4 (3)	O3—C18—H18B	111.4
C16—C11—C9	123.0 (2)	C19—C18—H18B	111.4
C11—C12—C13	120.7 (3)	H18A—C18—H18B	109.2
C14—C13—C12	120.0 (3)	C18—C19—H19A	109.5
C13—C14—C15	119.6 (3)	C18—C19—H19B	109.5
C16—C15—C14	120.4 (3)	H19A—C19—H19B	109.5
C15—C16—C11	120.8 (3)	C18—C19—H19C	109.5
O2—C17—O3	124.2 (3)	H19A—C19—H19C	109.5
O2—C17—C8	123.9 (3)	H19B—C19—H19C	109.5
O3—C17—C8	111.8 (3)	H19D—C19'—H19E	109.5
O3—C18—C19	102.0 (4)	H19D—C19'—H19F	109.5
C20—S2—C23	93.22 (14)	H19E—C19'—H19F	109.5
C36—O6—C37	116.0 (2)	C21—C20—H20	124.1
C21—C20—S2	111.8 (2)	S2—C20—H20	124.1
C20—C21—C22	112.2 (3)	C20—C21—H21	123.9
C23—C22—C21	114.8 (3)	C22—C21—H21	123.9
C23—C22—Br2	126.7 (2)	C24—C25—H25	118.1
C21—C22—Br2	118.4 (2)	C26—C25—H25	118.1
C22—C23—C24	133.3 (3)	C36—C27—H27	108.7
C22—C23—S2	107.9 (2)	C26—C27—H27	108.7
C24—C23—S2	118.8 (2)	C28—C27—H27	108.7
C25—C24—C23	123.8 (2)	C30—C28—H28	107.6
C25—C24—C29	119.0 (3)	C29—C28—H28	107.6
C23—C24—C29	117.1 (2)	C27—C28—H28	107.6
C24—C25—C26	123.8 (3)	C24—C29—H29A	108.9
O4—C26—C25	120.9 (3)	C28—C29—H29A	108.9
O4—C26—C27	120.3 (3)	C24—C29—H29B	108.9
C25—C26—C27	118.8 (2)	C28—C29—H29B	108.9
C36—C27—C26	107.7 (2)	H29A—C29—H29B	107.7
C36—C27—C28	112.0 (2)	C30—C31—H31	120.0
C26—C27—C28	111.1 (2)	C32—C31—H31	120.0
C30—C28—C29	109.2 (2)	C33—C32—H32	119.6
C30—C28—C27	114.3 (2)	C31—C32—H32	119.6
C29—C28—C27	110.2 (2)	C34—C33—H33	120.2
C24—C29—C28	113.6 (2)	C32—C33—H33	120.2
C31—C30—C35	118.6 (3)	C33—C34—H34	119.9
C31—C30—C28	122.5 (3)	C35—C34—H34	119.9
C35—C30—C28	118.7 (3)	C34—C35—H35	119.6
C30—C31—C32	120.0 (3)	C30—C35—H35	119.6
C33—C32—C31	120.7 (3)	O6—C37—H37A	110.2
C34—C33—C32	119.6 (3)	C38—C37—H37A	110.2
C33—C34—C35	120.2 (3)	O6—C37—H37B	110.2
C34—C35—C30	120.8 (3)	C38—C37—H37B	110.2
O5—C36—O6	124.0 (3)	H37A—C37—H37B	108.5
O5—C36—C27	124.5 (3)	C37—C38—H38A	109.5
O6—C36—C27	111.4 (2)	C37—C38—H38B	109.5
O6—C37—C38	107.5 (3)	H38A—C38—H38B	109.5
C2—C1—H1	124.2	C37—C38—H38C	109.5
S1—C1—H1	124.2	H38A—C38—H38C	109.5
C1—C2—H2	123.9	H38B—C38—H38C	109.5
C3—C2—H2	123.9

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇BrO₃S
M_r	405.32
Crystal system, space group	Triclinic, P1
Temperature (K)	130
a, b, c (Å)	8.8925 (8), 11.713 (2), 16.853 (2)
α, β, γ (°)	94.317 (11), 98.436 (10), 90.235 (13)
V (Å³)	1731.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.50
Crystal size (mm)	0.30 × 0.17 × 0.05

Data collection
Diffractometer	Bruker Nonius KappaCCD diffractometer
Absorption correction	Numerical (HABITUS; Herrendorf & Bärnighausen, 1997)
T_min, T_max	0.638, 0.843
No. of measured, independent and observed [I > 2σ(I)] reflections	40436, 7898, 6074
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.090, 1.04
No. of reflections	7898
No. of parameters	438
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.84, −0.54

Computer programs: COLLECT (Nonius, 1999), DIRAX (Duisenberg, 1992), EVALCCD (Duisenberg et al., 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2007), publCIF (Westrip, 2008).

Acknowledgements

The Swedish research council (VR) is acknowledged for providing funding for the single-crystal diffractometer.

References

Brandenburg, K. (2007). DIAMOND. Release 3.1e. Crystal Impact GbR, Bonn, Germany. Google Scholar
Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125–1150. Web of Science PubMed CAS Google Scholar
Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92–96. CrossRef CAS Web of Science IUCr Journals Google Scholar
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220–229. Web of Science CrossRef CAS IUCr Journals Google Scholar
Fischer, A., Yathirajan, H. S., Ashalatha, B. V., Narayana, B. & Sarojini, B. K. (2007a). Acta Cryst. E63, o254–o255. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fischer, A., Yathirajan, H. S., Ashalatha, B. V., Narayana, B. & Sarojini, B. K. (2007b). Acta Cryst. E63, o3616. Web of Science CSD CrossRef IUCr Journals Google Scholar
Herrendorf, W. & Bärnighausen, H. (1997). HABITUS. University of Karlsruhe, Germany. Google Scholar
House, H. O. (1972). Modern Synthetic Reactions, 2nd ed., pp. 595–632. Menlo Park, California: Benjamin-Cummings Pub. Co. Google Scholar
Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tabba, H. D., Yousef, N. M. & Alarab, M. M. (1995). Collect. Czech. Chem. Commun. 60, 594–604. CSD CrossRef CAS Web of Science Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar