organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890

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

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[Fischer, A., Yathirajan, H. S., Ashalatha, B. V., Narayana, B. & Sarojini, B. K. (2007a). Acta Cryst. E63, o254-o255.],b[Fischer, A., Yathirajan, H. S., Ashalatha, B. V., Narayana, B. & Sarojini, B. K. (2007b). Acta Cryst. E63, o3616.]). For related literature, see: House (1972[House, H. O. (1972). Modern Synthetic Reactions, 2nd ed., pp. 595-632. Menlo Park, California: Benjamin-Cummings Pub. Co.]); Tabba et al. (1995[Tabba, H. D., Yousef, N. M. & Alarab, M. M. (1995). Collect. Czech. Chem. Commun. 60, 594-604.]); Dimmock et al. (1999[Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125-1150.]).

[Scheme 1]

Experimental

Crystal data
  • C19H17BrO3S

  • Mr = 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[Herrendorf, W. & Bärnighausen, H. (1997). HABITUS. University of Karlsruhe, Germany.]) Tmin = 0.638, Tmax = 0.843

  • 40436 measured reflections

  • 7898 independent reflections

  • 6074 reflections with I > 2σ(I)

  • Rint = 0.073

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.089

  • S = 1.04

  • 7898 reflections

  • 438 parameters

  • H-atom parameters constrained

  • Δρmax = 0.84 e Å−3

  • Δρmin = −0.54 e Å−3

Data collection: COLLECT (Nonius, 1999[Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DIRAX (Duisenberg, 1992[Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96.]); data reduction: EVALCCD (Duisenberg et al., 2003[Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2007[Brandenburg, K. (2007). DIAMOND. Release 3.1e. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


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).

Refinement top

Hydrogen atoms were placed at calculated positions with C—H distances: 0.95, 0.98 and 0.99 Å for aromatic, methyl and methylene groups, respectively, and were included in the refinements in riding mode with Uiso = 1.2 and 1.5 time Ueq of the carrier atoms for non-methyl and methyl groups, respectively. A methyl C-atom of methoxy group in molecule 1 was disordered over two positions C19 and C19' with site occupation factors of 0.513 (6) and 0.487 (6), respectively.

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
[Figure 1] 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.
[Figure 2] 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
C19H17BrO3SZ = 4
Mr = 405.32F(000) = 824
Triclinic, P1Dx = 1.555 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.8925 (8) ÅCell parameters from 44 reflections
b = 11.713 (2) Åθ = 6.3–19.4°
c = 16.853 (2) ŵ = 2.50 mm1
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 tubeRint = 0.073
ϕ and ω scansθmax = 27.5°, θmin = 4.5°
Absorption correction: numerical
(HABITUS; Herrendorf & Bärnighausen, 1997)
h = 1111
Tmin = 0.638, Tmax = 0.843k = 1515
40436 measured reflectionsl = 2121
7898 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.090 w = 1/[σ2(Fo2) + (0.0305P)2 + 2.19P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
7898 reflectionsΔρmax = 0.84 e Å3
438 parametersΔρmin = 0.54 e Å3
0 restraints
Crystal data top
C19H17BrO3Sγ = 90.235 (13)°
Mr = 405.32V = 1731.3 (4) Å3
Triclinic, P1Z = 4
a = 8.8925 (8) ÅMo Kα radiation
b = 11.713 (2) ŵ = 2.50 mm1
c = 16.853 (2) ÅT = 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)
Tmin = 0.638, Tmax = 0.843Rint = 0.073
40436 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.090H-atom parameters constrained
S = 1.04Δρmax = 0.84 e Å3
7898 reflectionsΔρmin = 0.54 e Å3
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
xyzUiso*/UeqOcc. (<1)
Br10.99977 (4)0.72535 (2)0.421420 (19)0.03009 (9)
S10.66855 (8)0.46246 (6)0.45787 (4)0.02458 (16)
O11.1493 (2)0.73022 (18)0.71856 (13)0.0311 (5)
O21.1039 (3)0.52832 (19)0.83761 (14)0.0368 (5)
O31.0313 (3)0.69989 (19)0.88526 (14)0.0408 (6)
C10.6729 (3)0.4794 (3)0.35854 (18)0.0263 (6)
C20.7753 (3)0.5611 (2)0.34871 (18)0.0236 (6)
C30.8510 (3)0.6105 (2)0.42277 (17)0.0212 (6)
C40.8073 (3)0.5679 (2)0.49033 (17)0.0203 (6)
C50.8539 (3)0.5935 (2)0.57634 (17)0.0197 (6)
C60.9826 (3)0.6524 (2)0.60774 (18)0.0214 (6)
C71.0306 (3)0.6775 (2)0.69339 (18)0.0225 (6)
C80.9305 (3)0.6373 (2)0.75173 (17)0.0213 (6)
C90.8343 (3)0.5321 (2)0.71617 (17)0.0208 (6)
C100.7514 (3)0.5522 (2)0.63266 (16)0.0206 (6)
C110.7227 (3)0.4959 (2)0.76997 (17)0.0209 (6)
C120.7020 (3)0.3799 (2)0.77736 (19)0.0285 (7)
C130.5923 (4)0.3416 (3)0.8206 (2)0.0361 (8)
C140.5035 (4)0.4191 (3)0.8572 (2)0.0374 (8)
C150.5246 (4)0.5351 (3)0.8508 (2)0.0350 (7)
C160.6338 (3)0.5729 (2)0.80828 (18)0.0263 (6)
C171.0313 (3)0.6139 (2)0.82876 (18)0.0251 (6)
C181.1320 (5)0.6868 (4)0.9614 (2)0.0555 (11)
C191.2037 (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)
Br20.50916 (3)0.75741 (2)0.418423 (18)0.02812 (9)
S20.16982 (8)1.01911 (6)0.45701 (4)0.02397 (16)
O40.6550 (2)0.81534 (18)0.71690 (13)0.0306 (5)
O50.6026 (2)1.03913 (17)0.84067 (13)0.0324 (5)
O60.5409 (2)0.86917 (17)0.88122 (12)0.0286 (5)
C200.1748 (3)0.9822 (3)0.35764 (18)0.0261 (6)
C210.2799 (3)0.9014 (2)0.34699 (18)0.0241 (6)
C220.3574 (3)0.8687 (2)0.42091 (17)0.0201 (6)
C230.3116 (3)0.9236 (2)0.48873 (17)0.0195 (6)
C240.3592 (3)0.9170 (2)0.57463 (17)0.0186 (6)
C250.4871 (3)0.8656 (2)0.60608 (17)0.0215 (6)
C260.5353 (3)0.8602 (2)0.69166 (18)0.0217 (6)
C270.4338 (3)0.9107 (2)0.75024 (16)0.0190 (6)
C280.3404 (3)1.0092 (2)0.71490 (16)0.0191 (6)
C290.2568 (3)0.9709 (2)0.63110 (16)0.0202 (6)
C300.2268 (3)1.0582 (2)0.76721 (17)0.0218 (6)
C310.1404 (3)0.9897 (3)0.80725 (19)0.0290 (7)
C320.0259 (4)1.0375 (3)0.8464 (2)0.0387 (8)
C330.0024 (4)1.1527 (3)0.8463 (2)0.0412 (9)
C340.0858 (4)1.2217 (3)0.8088 (2)0.0396 (8)
C350.1999 (4)1.1751 (3)0.76958 (18)0.0293 (7)
C360.5346 (3)0.9491 (2)0.82818 (18)0.0225 (6)
C370.6474 (4)0.8921 (3)0.9551 (2)0.0422 (9)
C380.6280 (6)0.7991 (4)1.0081 (3)0.0655 (13)
H10.61110.43690.31550.032*
H20.79400.58250.29770.028*
H61.04510.67880.57160.026*
H80.86080.70050.76400.026*
H90.90500.46730.70970.025*
H10A0.70060.48000.60830.025*
H10B0.67180.60950.63830.025*
H120.76320.32600.75260.034*
H130.57870.26200.82500.043*
H140.42840.39330.88650.045*
H150.46350.58880.87580.042*
H160.64840.65270.80520.032*
H18A1.21020.62890.95440.067*0.513 (6)
H18B1.07400.66511.00400.067*0.513 (6)
H19A1.27460.81031.03170.093*0.513 (6)
H19B1.12350.86400.98720.093*0.513 (6)
H19C1.25810.82830.93760.093*0.513 (6)
H18C1.14480.76110.99390.067*0.487 (6)
H18D1.23300.66180.95000.067*0.487 (6)
H19D1.12870.58561.06100.093*0.487 (6)
H19E1.04880.52110.97840.093*0.487 (6)
H19F0.96190.62031.02260.093*0.487 (6)
H200.11171.01430.31490.031*
H210.29920.87040.29580.029*
H250.54900.83100.57000.026*
H270.36270.84950.76110.023*
H280.41281.07230.70870.023*
H29A0.17610.91490.63660.024*
H29B0.20741.03790.60680.024*
H310.15930.91020.80800.035*
H320.03340.99000.87350.046*
H330.08231.18430.87200.049*
H340.06841.30160.80970.048*
H350.26061.22360.74400.035*
H37A0.62660.96710.98200.051*
H37B0.75270.89380.94290.051*
H38A0.52280.79681.01850.098*
H38B0.69610.81351.05920.098*
H38C0.65240.72570.98160.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.03887 (18)0.02276 (15)0.02951 (18)0.00756 (12)0.00681 (13)0.00493 (12)
S10.0186 (3)0.0318 (4)0.0222 (4)0.0066 (3)0.0026 (3)0.0035 (3)
O10.0262 (11)0.0335 (12)0.0313 (12)0.0141 (9)0.0019 (9)0.0072 (9)
O20.0390 (13)0.0326 (12)0.0364 (14)0.0065 (10)0.0033 (10)0.0034 (10)
O30.0517 (14)0.0370 (13)0.0294 (13)0.0003 (11)0.0008 (11)0.0113 (10)
C10.0234 (15)0.0328 (16)0.0213 (15)0.0020 (12)0.0015 (12)0.0043 (12)
C20.0249 (14)0.0255 (14)0.0206 (15)0.0069 (12)0.0031 (12)0.0042 (12)
C30.0198 (13)0.0177 (13)0.0267 (16)0.0039 (11)0.0057 (11)0.0007 (11)
C40.0153 (13)0.0179 (13)0.0273 (16)0.0020 (10)0.0036 (11)0.0022 (11)
C50.0190 (13)0.0163 (13)0.0241 (15)0.0027 (10)0.0046 (11)0.0010 (11)
C60.0168 (13)0.0217 (14)0.0263 (16)0.0031 (11)0.0059 (11)0.0003 (11)
C70.0200 (14)0.0172 (13)0.0297 (16)0.0018 (11)0.0040 (12)0.0026 (11)
C80.0195 (13)0.0202 (13)0.0231 (15)0.0019 (11)0.0009 (11)0.0009 (11)
C90.0229 (14)0.0175 (13)0.0214 (15)0.0033 (11)0.0027 (11)0.0020 (11)
C100.0184 (13)0.0236 (14)0.0191 (15)0.0044 (11)0.0020 (11)0.0011 (11)
C110.0217 (14)0.0219 (14)0.0180 (14)0.0040 (11)0.0007 (11)0.0012 (11)
C120.0357 (17)0.0211 (14)0.0285 (17)0.0019 (13)0.0047 (13)0.0012 (12)
C130.048 (2)0.0258 (16)0.0357 (19)0.0106 (15)0.0062 (16)0.0073 (14)
C140.0434 (19)0.0421 (19)0.0288 (18)0.0178 (16)0.0123 (15)0.0051 (15)
C150.0362 (18)0.0385 (18)0.0319 (19)0.0043 (15)0.0127 (14)0.0016 (14)
C160.0298 (16)0.0204 (14)0.0287 (17)0.0031 (12)0.0044 (13)0.0023 (12)
C170.0242 (15)0.0249 (15)0.0253 (16)0.0048 (12)0.0034 (12)0.0022 (12)
C180.061 (3)0.070 (3)0.028 (2)0.002 (2)0.0077 (18)0.0136 (19)
C190.061 (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)
Br20.03497 (17)0.02113 (15)0.02934 (17)0.00523 (12)0.00939 (13)0.00052 (12)
S20.0190 (3)0.0310 (4)0.0221 (4)0.0037 (3)0.0031 (3)0.0031 (3)
O40.0284 (11)0.0332 (11)0.0313 (12)0.0125 (9)0.0048 (9)0.0088 (9)
O50.0354 (12)0.0249 (11)0.0342 (13)0.0089 (9)0.0044 (10)0.0040 (9)
O60.0309 (11)0.0289 (11)0.0246 (12)0.0072 (9)0.0035 (9)0.0083 (9)
C200.0233 (15)0.0327 (16)0.0220 (16)0.0025 (12)0.0013 (12)0.0041 (12)
C210.0248 (14)0.0259 (14)0.0216 (15)0.0086 (12)0.0060 (12)0.0024 (12)
C220.0169 (13)0.0174 (13)0.0259 (16)0.0049 (10)0.0043 (11)0.0005 (11)
C230.0162 (13)0.0165 (13)0.0263 (15)0.0050 (10)0.0049 (11)0.0023 (11)
C240.0186 (13)0.0147 (12)0.0232 (15)0.0047 (10)0.0063 (11)0.0004 (11)
C250.0214 (14)0.0184 (13)0.0262 (16)0.0001 (11)0.0089 (11)0.0010 (11)
C260.0199 (14)0.0160 (13)0.0301 (16)0.0012 (11)0.0049 (12)0.0050 (11)
C270.0201 (13)0.0163 (13)0.0211 (15)0.0036 (10)0.0034 (11)0.0036 (11)
C280.0183 (13)0.0182 (13)0.0204 (15)0.0007 (10)0.0022 (11)0.0007 (11)
C290.0187 (13)0.0214 (13)0.0215 (15)0.0018 (11)0.0042 (11)0.0052 (11)
C300.0195 (13)0.0277 (14)0.0161 (14)0.0044 (11)0.0021 (11)0.0022 (11)
C310.0287 (16)0.0287 (16)0.0294 (17)0.0021 (13)0.0065 (13)0.0024 (13)
C320.0329 (18)0.056 (2)0.0289 (19)0.0015 (16)0.0122 (14)0.0029 (16)
C330.0376 (19)0.059 (2)0.0263 (18)0.0207 (17)0.0074 (15)0.0065 (16)
C340.054 (2)0.0369 (18)0.0260 (18)0.0212 (16)0.0003 (16)0.0033 (14)
C350.0348 (17)0.0294 (16)0.0230 (16)0.0075 (13)0.0020 (13)0.0019 (13)
C360.0186 (13)0.0240 (15)0.0252 (16)0.0005 (11)0.0033 (11)0.0033 (12)
C370.048 (2)0.044 (2)0.0289 (19)0.0130 (16)0.0134 (15)0.0074 (15)
C380.095 (3)0.053 (2)0.040 (2)0.020 (2)0.027 (2)0.0200 (19)
Geometric parameters (Å, º) top
Br1—C31.888 (3)C30—C311.385 (4)
S1—C11.706 (3)C30—C351.392 (4)
S1—C41.743 (3)C31—C321.393 (4)
O1—C71.225 (3)C32—C331.376 (5)
O2—C171.201 (3)C33—C341.374 (5)
O3—C171.333 (4)C34—C351.386 (4)
O3—C181.474 (4)C37—C381.486 (5)
C1—C21.355 (4)C1—H10.9500
C2—C31.410 (4)C2—H20.9500
C3—C41.382 (4)C6—H60.9500
C4—C51.455 (4)C8—H81.0000
C5—C61.353 (4)C9—H91.0000
C5—C101.512 (4)C10—H10A0.9900
C6—C71.451 (4)C10—H10B0.9900
C7—C81.519 (4)C12—H120.9500
C8—C171.511 (4)C13—H130.9500
C8—C91.530 (4)C14—H140.9500
C9—C111.520 (4)C15—H150.9500
C9—C101.526 (4)C16—H160.9500
C11—C121.389 (4)C18—H18A0.9900
C11—C161.390 (4)C18—H18B0.9900
C12—C131.394 (4)C19—H19A0.9800
C13—C141.378 (5)C19—H19B0.9800
C14—C151.386 (5)C19—H19C0.9800
C15—C161.380 (4)C19'—H19D0.9800
C18—C191.554 (9)C19'—H19E0.9800
Br2—C221.883 (3)C19'—H19F0.9800
S2—C201.704 (3)C20—H200.9500
S2—C231.741 (3)C21—H210.9500
O4—C261.223 (3)C25—H250.9500
O5—C361.203 (3)C27—H271.0000
O6—C361.339 (3)C28—H281.0000
O6—C371.457 (4)C29—H29A0.9900
C20—C211.358 (4)C29—H29B0.9900
C21—C221.414 (4)C31—H310.9500
C22—C231.384 (4)C32—H320.9500
C23—C241.455 (4)C33—H330.9500
C24—C251.351 (4)C34—H340.9500
C24—C291.520 (4)C35—H350.9500
C25—C261.449 (4)C37—H37A0.9900
C26—C271.524 (4)C37—H37B0.9900
C27—C361.515 (4)C38—H38A0.9800
C27—C281.534 (4)C38—H38B0.9800
C28—C301.525 (4)C38—H38C0.9800
C28—C291.530 (4)
C1—S1—C493.37 (14)C5—C6—H6118.1
C17—O3—C18115.6 (3)C7—C6—H6118.1
C2—C1—S1111.6 (2)C17—C8—H8108.4
C1—C2—C3112.3 (3)C7—C8—H8108.4
C4—C3—C2115.1 (2)C9—C8—H8108.4
C4—C3—Br1126.4 (2)C11—C9—H9107.5
C2—C3—Br1118.5 (2)C10—C9—H9107.5
C3—C4—C5133.4 (2)C8—C9—H9107.5
C3—C4—S1107.7 (2)C5—C10—H10A108.8
C5—C4—S1118.9 (2)C9—C10—H10A108.8
C6—C5—C4123.3 (3)C5—C10—H10B108.8
C6—C5—C10119.0 (3)C9—C10—H10B108.8
C4—C5—C10117.7 (2)H10A—C10—H10B107.7
C5—C6—C7123.8 (3)C11—C12—H12119.6
O1—C7—C6121.0 (3)C13—C12—H12119.6
O1—C7—C8120.3 (3)C14—C13—H13120.0
C6—C7—C8118.6 (2)C12—C13—H13120.0
C17—C8—C7108.0 (2)C13—C14—H14120.2
C17—C8—C9111.7 (2)C15—C14—H14120.2
C7—C8—C9111.9 (2)C16—C15—H15119.8
C11—C9—C10110.4 (2)C14—C15—H15119.8
C11—C9—C8113.2 (2)C15—C16—H16119.6
C10—C9—C8110.5 (2)C11—C16—H16119.6
C5—C10—C9113.8 (2)O3—C18—H18A111.4
C12—C11—C16118.4 (3)C19—C18—H18A111.4
C12—C11—C9118.4 (3)O3—C18—H18B111.4
C16—C11—C9123.0 (2)C19—C18—H18B111.4
C11—C12—C13120.7 (3)H18A—C18—H18B109.2
C14—C13—C12120.0 (3)C18—C19—H19A109.5
C13—C14—C15119.6 (3)C18—C19—H19B109.5
C16—C15—C14120.4 (3)H19A—C19—H19B109.5
C15—C16—C11120.8 (3)C18—C19—H19C109.5
O2—C17—O3124.2 (3)H19A—C19—H19C109.5
O2—C17—C8123.9 (3)H19B—C19—H19C109.5
O3—C17—C8111.8 (3)H19D—C19'—H19E109.5
O3—C18—C19102.0 (4)H19D—C19'—H19F109.5
C20—S2—C2393.22 (14)H19E—C19'—H19F109.5
C36—O6—C37116.0 (2)C21—C20—H20124.1
C21—C20—S2111.8 (2)S2—C20—H20124.1
C20—C21—C22112.2 (3)C20—C21—H21123.9
C23—C22—C21114.8 (3)C22—C21—H21123.9
C23—C22—Br2126.7 (2)C24—C25—H25118.1
C21—C22—Br2118.4 (2)C26—C25—H25118.1
C22—C23—C24133.3 (3)C36—C27—H27108.7
C22—C23—S2107.9 (2)C26—C27—H27108.7
C24—C23—S2118.8 (2)C28—C27—H27108.7
C25—C24—C23123.8 (2)C30—C28—H28107.6
C25—C24—C29119.0 (3)C29—C28—H28107.6
C23—C24—C29117.1 (2)C27—C28—H28107.6
C24—C25—C26123.8 (3)C24—C29—H29A108.9
O4—C26—C25120.9 (3)C28—C29—H29A108.9
O4—C26—C27120.3 (3)C24—C29—H29B108.9
C25—C26—C27118.8 (2)C28—C29—H29B108.9
C36—C27—C26107.7 (2)H29A—C29—H29B107.7
C36—C27—C28112.0 (2)C30—C31—H31120.0
C26—C27—C28111.1 (2)C32—C31—H31120.0
C30—C28—C29109.2 (2)C33—C32—H32119.6
C30—C28—C27114.3 (2)C31—C32—H32119.6
C29—C28—C27110.2 (2)C34—C33—H33120.2
C24—C29—C28113.6 (2)C32—C33—H33120.2
C31—C30—C35118.6 (3)C33—C34—H34119.9
C31—C30—C28122.5 (3)C35—C34—H34119.9
C35—C30—C28118.7 (3)C34—C35—H35119.6
C30—C31—C32120.0 (3)C30—C35—H35119.6
C33—C32—C31120.7 (3)O6—C37—H37A110.2
C34—C33—C32119.6 (3)C38—C37—H37A110.2
C33—C34—C35120.2 (3)O6—C37—H37B110.2
C34—C35—C30120.8 (3)C38—C37—H37B110.2
O5—C36—O6124.0 (3)H37A—C37—H37B108.5
O5—C36—C27124.5 (3)C37—C38—H38A109.5
O6—C36—C27111.4 (2)C37—C38—H38B109.5
O6—C37—C38107.5 (3)H38A—C38—H38B109.5
C2—C1—H1124.2C37—C38—H38C109.5
S1—C1—H1124.2H38A—C38—H38C109.5
C1—C2—H2123.9H38B—C38—H38C109.5
C3—C2—H2123.9

Experimental details

Crystal data
Chemical formulaC19H17BrO3S
Mr405.32
Crystal system, space groupTriclinic, 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)
V3)1731.3 (4)
Z4
Radiation typeMo Kα
µ (mm1)2.50
Crystal size (mm)0.30 × 0.17 × 0.05
Data collection
DiffractometerBruker Nonius KappaCCD
diffractometer
Absorption correctionNumerical
(HABITUS; Herrendorf & Bärnighausen, 1997)
Tmin, Tmax0.638, 0.843
No. of measured, independent and
observed [I > 2σ(I)] reflections
40436, 7898, 6074
Rint0.073
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.090, 1.04
No. of reflections7898
No. of parameters438
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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

First citationBrandenburg, K. (2007). DIAMOND. Release 3.1e. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationDimmock, 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
First citationDuisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92–96.  CrossRef CAS Web of Science IUCr Journals Google Scholar
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First citationHerrendorf, W. & Bärnighausen, H. (1997). HABITUS. University of Karlsruhe, Germany.  Google Scholar
First citationHouse, H. O. (1972). Modern Synthetic Reactions, 2nd ed., pp. 595–632. Menlo Park, California: Benjamin-Cummings Pub. Co.  Google Scholar
First citationNonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTabba, H. D., Yousef, N. M. & Alarab, M. M. (1995). Collect. Czech. Chem. Commun. 60, 594–604.  CSD CrossRef CAS Web of Science Google Scholar
First citationWestrip, S. P. (2008). publCIF. In preparation.  Google Scholar

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