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The enone fragment, thio­phene ring and benzene ring of the title mol­ecule, C13H9BrOS, are each essentially planar. The thio­phene ring is disordered over two sites, corresponding to a rotation of approximately 180° about the single C—C bond to which it is attached. The crystal packing is stabilized by weak inter­molecular C—H...π inter­actions involving the thio­phene and benzene rings, and mol­ecules are stacked along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026079/lh2122sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026079/lh2122Isup2.hkl
Contains datablock I

CCDC reference: 621400

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.001 Å
  • Disorder in main residue
  • R factor = 0.029
  • wR factor = 0.075
  • Data-to-parameter ratio = 40.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.33 PLAT301_ALERT_3_C Main Residue Disorder ......................... 20.00 Perc. PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. S1 .. 3.46 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

1-(4-Bromophenyl)-3-(2-thienyl)prop-2-en-1-one top
Crystal data top
C13H9BrOSF(000) = 584
Mr = 293.17Dx = 1.732 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7622 reflections
a = 14.0993 (3) Åθ = 2.1–40.0°
b = 13.8355 (3) ŵ = 3.81 mm1
c = 5.8022 (1) ÅT = 100 K
β = 96.634 (1)°Block, yellow
V = 1124.26 (4) Å30.44 × 0.42 × 0.38 mm
Z = 4
Data collection top
Bruker SMART APEX-2 CCD area-detector
diffractometer
6876 independent reflections
Radiation source: fine-focus sealed tube5478 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
Detector resolution: 8.33 pixels mm-1θmax = 40.0°, θmin = 2.1°
ω scansh = 2525
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 2425
Tmin = 0.204, Tmax = 0.234l = 1010
64573 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H-atom parameters constrained
wR(F2) = 0.076 w = 1/[σ2(Fo2) + (0.0367P)2 + 0.474P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.003
6876 reflectionsΔρmax = 1.36 e Å3
168 parametersΔρmin = 0.58 e Å3
113 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0100 (7)
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)
Br10.421686 (7)0.628688 (9)0.36886 (2)0.02014 (4)
O10.02602 (6)0.61935 (7)0.69935 (15)0.02218 (16)
C10.12901 (7)0.59062 (8)0.25390 (17)0.01478 (15)
H1A0.08470.56940.13330.018*
C20.22604 (7)0.58965 (8)0.22791 (17)0.01523 (15)
H2A0.24710.56660.09220.018*
C30.29057 (7)0.62368 (7)0.40797 (18)0.01426 (15)
C40.26155 (7)0.65628 (8)0.61536 (18)0.01518 (15)
H4A0.30600.67820.73490.018*
C50.16488 (7)0.65549 (8)0.64017 (17)0.01440 (15)
H5A0.14430.67660.77830.017*
C60.09805 (7)0.62331 (7)0.46004 (17)0.01319 (14)
C70.00468 (7)0.62187 (7)0.49973 (18)0.01514 (15)
C80.07742 (7)0.62506 (8)0.29640 (19)0.01620 (16)
H8A0.06000.64060.15120.019*
C90.16920 (7)0.60545 (8)0.32084 (18)0.01495 (15)
H9A0.18290.58440.46560.018*
C100.24787 (7)0.61450 (7)0.14002 (18)0.01448 (15)
S10.35947 (4)0.57632 (5)0.18350 (9)0.01625 (10)0.7909 (19)
C110.40853 (12)0.61584 (15)0.0830 (4)0.0177 (3)0.7909 (19)
H11A0.47290.61000.13840.021*0.7909 (19)
C120.34148 (18)0.65723 (15)0.2053 (3)0.0172 (3)0.7909 (19)
H12A0.35490.68260.35390.021*0.7909 (19)
C130.2503 (4)0.6568 (4)0.0799 (10)0.0157 (6)0.7909 (19)
H13A0.19660.68220.13710.019*0.7909 (19)
S1X0.2415 (4)0.6698 (4)0.1061 (9)0.0141 (5)0.2091 (19)
C11X0.3606 (6)0.6531 (7)0.1906 (17)0.0190 (19)*0.2091 (19)
H11B0.39090.67520.33180.023*0.2091 (19)
C12X0.4065 (5)0.6055 (6)0.0352 (13)0.0139 (14)*0.2091 (19)
H12B0.47100.58950.05750.017*0.2091 (19)
C13X0.3447 (7)0.5827 (9)0.1662 (19)0.021 (2)*0.2091 (19)
H13B0.36290.55180.29650.025*0.2091 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.01054 (4)0.02712 (6)0.02297 (6)0.00091 (3)0.00286 (3)0.00181 (4)
O10.0147 (3)0.0366 (5)0.0156 (3)0.0017 (3)0.0033 (2)0.0008 (3)
C10.0131 (3)0.0175 (4)0.0136 (4)0.0010 (3)0.0011 (3)0.0012 (3)
C20.0137 (4)0.0182 (4)0.0140 (4)0.0004 (3)0.0023 (3)0.0011 (3)
C30.0106 (3)0.0164 (4)0.0158 (4)0.0005 (3)0.0016 (3)0.0005 (3)
C40.0126 (3)0.0173 (4)0.0153 (4)0.0006 (3)0.0001 (3)0.0019 (3)
C50.0131 (3)0.0167 (4)0.0134 (4)0.0010 (3)0.0010 (3)0.0012 (3)
C60.0116 (3)0.0147 (4)0.0132 (4)0.0003 (3)0.0011 (3)0.0009 (3)
C70.0122 (3)0.0176 (4)0.0156 (4)0.0001 (3)0.0016 (3)0.0009 (3)
C80.0123 (3)0.0202 (4)0.0160 (4)0.0007 (3)0.0011 (3)0.0021 (3)
C90.0119 (3)0.0173 (4)0.0155 (4)0.0012 (3)0.0008 (3)0.0007 (3)
C100.0119 (3)0.0163 (4)0.0151 (4)0.0008 (3)0.0011 (3)0.0005 (3)
S10.01063 (17)0.0224 (2)0.01579 (18)0.00097 (14)0.00182 (13)0.00210 (12)
C110.0131 (5)0.0224 (8)0.0168 (8)0.0008 (4)0.0020 (5)0.0017 (6)
C120.0186 (8)0.0200 (7)0.0130 (6)0.0006 (6)0.0016 (5)0.0015 (4)
C130.0124 (10)0.0183 (14)0.0171 (13)0.0037 (8)0.0046 (8)0.0006 (8)
S1X0.0103 (10)0.0184 (14)0.0139 (11)0.0018 (8)0.0033 (7)0.0014 (7)
Geometric parameters (Å, º) top
Br1—C31.8897 (10)C9—H9A0.9300
O1—C71.2304 (13)C10—C131.400 (5)
C1—C21.3936 (14)C10—C13X1.459 (9)
C1—C61.3952 (14)C10—S1X1.631 (4)
C1—H1A0.9300C10—S11.7059 (12)
C2—C31.3861 (14)S1—C111.709 (2)
C2—H2A0.9300C11—C121.371 (3)
C3—C41.3902 (14)C11—H11A0.9300
C4—C51.3871 (14)C12—C131.403 (6)
C4—H4A0.9300C12—H12A0.9300
C5—C61.3967 (14)C13—H13A0.9300
C5—H5A0.9300S1X—C11X1.710 (9)
C6—C71.4927 (14)C11X—C12X1.342 (10)
C7—C81.4717 (15)C11X—H11B0.9300
C8—C91.3456 (14)C12X—C13X1.411 (12)
C8—H8A0.9300C12X—H12B0.9300
C9—C101.4415 (14)C13X—H13B0.9300
C2—C1—C6120.28 (9)C13—C10—C13X107.3 (5)
C2—C1—H1A119.9C9—C10—C13X123.3 (4)
C6—C1—H1A119.9C9—C10—S1X124.19 (19)
C3—C2—C1118.83 (9)C13X—C10—S1X112.3 (4)
C3—C2—H2A120.6C13—C10—S1109.8 (2)
C1—C2—H2A120.6C9—C10—S1120.72 (8)
C2—C3—C4121.97 (9)S1X—C10—S1114.83 (19)
C2—C3—Br1119.21 (8)C10—S1—C1192.92 (8)
C4—C3—Br1118.81 (7)C12—C11—S1111.75 (14)
C5—C4—C3118.57 (9)C12—C11—H11A124.1
C5—C4—H4A120.7S1—C11—H11A124.1
C3—C4—H4A120.7C11—C12—C13112.0 (2)
C4—C5—C6120.73 (9)C11—C12—H12A124.0
C4—C5—H5A119.6C13—C12—H12A124.0
C6—C5—H5A119.6C10—C13—C12113.5 (3)
C1—C6—C5119.60 (9)C10—C13—H13A123.2
C1—C6—C7122.23 (9)C12—C13—H13A123.2
C5—C6—C7118.14 (9)C10—S1X—C11X92.1 (4)
O1—C7—C8122.13 (10)C12X—C11X—S1X114.0 (7)
O1—C7—C6119.52 (9)C12X—C11X—H11B123.0
C8—C7—C6118.34 (9)S1X—C11X—H11B123.0
C9—C8—C7119.94 (10)C11X—C12X—C13X111.5 (8)
C9—C8—H8A120.0C11X—C12X—H12B124.3
C7—C8—H8A120.0C13X—C12X—H12B124.2
C8—C9—C10125.05 (10)C12X—C13X—C10110.0 (7)
C8—C9—H9A117.5C12X—C13X—H13B125.0
C10—C9—H9A117.5C10—C13X—H13B125.0
C13—C10—C9129.4 (2)
C6—C1—C2—C31.44 (15)C9—C10—S1—C11176.75 (11)
C1—C2—C3—C41.71 (16)C13X—C10—S1—C1111 (11)
C1—C2—C3—Br1176.90 (8)S1X—C10—S1—C112.4 (3)
C2—C3—C4—C50.76 (16)C10—S1—C11—C120.28 (16)
Br1—C3—C4—C5177.86 (8)S1—C11—C12—C130.3 (4)
C3—C4—C5—C60.48 (16)C9—C10—C13—C12176.5 (2)
C2—C1—C6—C50.26 (15)C13X—C10—C13—C120.6 (7)
C2—C1—C6—C7177.40 (9)S1X—C10—C13—C12155 (6)
C4—C5—C6—C10.72 (15)S1—C10—C13—C120.1 (5)
C4—C5—C6—C7178.47 (10)C11—C12—C13—C100.1 (6)
C1—C6—C7—O1155.50 (11)C13—C10—S1X—C11X24 (5)
C5—C6—C7—O122.19 (15)C9—C10—S1X—C11X175.9 (4)
C1—C6—C7—C825.42 (15)C13X—C10—S1X—C11X1.1 (7)
C5—C6—C7—C8156.89 (10)S1—C10—S1X—C11X1.8 (5)
O1—C7—C8—C913.63 (17)C10—S1X—C11X—C12X0.3 (8)
C6—C7—C8—C9167.32 (10)S1X—C11X—C12X—C13X1.6 (12)
C7—C8—C9—C10174.21 (10)C11X—C12X—C13X—C102.4 (12)
C8—C9—C10—C1310.2 (4)C13—C10—C13X—C12X0.3 (10)
C8—C9—C10—C13X173.1 (6)C9—C10—C13X—C12X177.0 (5)
C8—C9—C10—S1X12.7 (3)S1X—C10—C13X—C12X2.2 (10)
C8—C9—C10—S1173.54 (9)S1—C10—C13X—C12X169 (12)
C13—C10—S1—C110.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···Cg1i0.932.903.546 (2)128
C2—H2A···Cg2i0.932.913.558 (4)128
C5—H5A···Cg3ii0.932.983.507 (1)118
C9—H9A···Cg3iii0.932.943.504 (1)120
C12—H12A···Cg1iv0.932.883.528 (2)128
C12—H12A···Cg2iv0.932.863.508 (4)128
Symmetry codes: (i) x, y+1, z; (ii) x, y+3/2, z+1/2; (iii) x, y+1, z+1; (iv) x, y+3/2, z1/2.
 

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