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In the title compound, C15H10Br2O, the dihedral angle between the benzene rings is 48.0 (1)°. The crystal structure is stabilized by weak inter­molecular Br...Br contacts and C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806017983/cv2052sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806017983/cv2052Isup2.hkl
Contains datablock I

CCDC reference: 610748

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.047
  • wR factor = 0.109
  • Data-to-parameter ratio = 18.2

checkCIF/PLATON results

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Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.89
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.895 Tmax scaled 0.474 Tmin scaled 0.113
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion

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, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

3-(3-Bromophenyl)-1-(4-bromophenyl)prop-2-en-1-one top
Crystal data top
C15H10Br2OF(000) = 712
Mr = 366.05Dx = 1.872 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6169 reflections
a = 7.1411 (2) Åθ = 2.6–27.5°
b = 31.4292 (8) ŵ = 6.23 mm1
c = 5.7876 (2) ÅT = 100 K
β = 91.275 (2)°Block, yellow
V = 1298.64 (7) Å30.40 × 0.20 × 0.12 mm
Z = 4
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
2962 independent reflections
Radiation source: fine-focus sealed tube2448 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 8.33 pixels mm-1θmax = 27.5°, θmin = 2.6°
ω scansh = 97
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 4039
Tmin = 0.126, Tmax = 0.530l = 77
14661 measured 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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.20 w = 1/[σ2(Fo2) + (0.0308P)2 + 4.6217P]
where P = (Fo2 + 2Fc2)/3
2962 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 1.05 e Å3
0 restraintsΔρmin = 0.71 e Å3
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*/Ueq
Br10.91718 (7)0.210296 (15)0.86868 (8)0.03381 (15)
Br20.68211 (7)0.211369 (15)0.61013 (8)0.03415 (15)
O10.7726 (5)0.02389 (10)0.2759 (5)0.0291 (7)
C10.9022 (6)0.07989 (15)0.7967 (7)0.0257 (9)
H1A0.93110.05650.88920.031*
C20.9380 (6)0.12056 (15)0.8782 (7)0.0265 (9)
H2A0.99710.12461.02130.032*
C30.8849 (6)0.15502 (14)0.7444 (7)0.0244 (9)
C40.8085 (6)0.15005 (15)0.5223 (8)0.0277 (9)
H4A0.77890.17360.43140.033*
C50.7777 (6)0.10916 (15)0.4399 (7)0.0249 (9)
H5A0.72640.10520.29240.030*
C60.8232 (6)0.07378 (14)0.5774 (7)0.0235 (9)
C70.7800 (6)0.03038 (14)0.4843 (7)0.0247 (9)
C80.7435 (6)0.00407 (15)0.6535 (7)0.0261 (9)
H8A0.72970.00260.80860.031*
C90.7305 (6)0.04422 (15)0.5856 (7)0.0245 (9)
H9A0.75330.04940.43050.029*
C100.6844 (6)0.08145 (14)0.7246 (7)0.0230 (9)
C110.7100 (6)0.12177 (14)0.6313 (7)0.0240 (9)
H11A0.76410.12470.48740.029*
C120.6555 (6)0.15750 (14)0.7512 (7)0.0236 (9)
C130.5788 (6)0.15431 (15)0.9688 (8)0.0270 (9)
H13A0.54430.17861.04960.032*
C140.5548 (7)0.11412 (15)1.0632 (8)0.0288 (10)
H14A0.50270.11151.20840.035*
C150.6072 (6)0.07779 (15)0.9443 (7)0.0257 (9)
H15A0.59110.05111.01030.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0377 (3)0.0258 (3)0.0379 (3)0.0045 (2)0.0003 (2)0.00326 (19)
Br20.0443 (3)0.0220 (2)0.0362 (3)0.0028 (2)0.0026 (2)0.00169 (19)
O10.0351 (18)0.0299 (18)0.0224 (15)0.0006 (14)0.0005 (13)0.0002 (13)
C10.029 (2)0.025 (2)0.023 (2)0.0007 (18)0.0013 (17)0.0030 (17)
C20.021 (2)0.035 (3)0.023 (2)0.0013 (18)0.0034 (17)0.0017 (18)
C30.027 (2)0.022 (2)0.024 (2)0.0036 (17)0.0030 (17)0.0016 (16)
C40.028 (2)0.025 (2)0.030 (2)0.0006 (18)0.0045 (18)0.0046 (18)
C50.020 (2)0.035 (3)0.020 (2)0.0020 (18)0.0008 (16)0.0020 (17)
C60.022 (2)0.027 (2)0.022 (2)0.0021 (17)0.0044 (16)0.0021 (16)
C70.023 (2)0.026 (2)0.025 (2)0.0016 (17)0.0022 (17)0.0024 (17)
C80.027 (2)0.028 (2)0.023 (2)0.0004 (18)0.0022 (17)0.0016 (17)
C90.022 (2)0.030 (2)0.022 (2)0.0030 (18)0.0017 (16)0.0006 (17)
C100.024 (2)0.023 (2)0.022 (2)0.0008 (17)0.0009 (16)0.0003 (16)
C110.024 (2)0.025 (2)0.023 (2)0.0024 (17)0.0003 (16)0.0004 (16)
C120.026 (2)0.019 (2)0.026 (2)0.0022 (17)0.0028 (17)0.0005 (16)
C130.030 (2)0.026 (2)0.025 (2)0.0003 (18)0.0010 (18)0.0030 (17)
C140.027 (2)0.036 (3)0.024 (2)0.0015 (19)0.0023 (17)0.0003 (18)
C150.030 (2)0.026 (2)0.021 (2)0.0022 (18)0.0036 (17)0.0012 (16)
Geometric parameters (Å, º) top
Br1—C31.892 (4)C8—C91.324 (6)
Br2—C121.891 (4)C8—H8A0.9300
O1—C71.223 (5)C9—C101.462 (6)
C1—C21.385 (7)C9—H9A0.9300
C1—C61.391 (6)C10—C111.392 (6)
C1—H1A0.9300C10—C151.402 (6)
C2—C31.380 (6)C11—C121.380 (6)
C2—H2A0.9300C11—H11A0.9300
C3—C41.394 (6)C12—C131.388 (6)
C4—C51.386 (6)C13—C141.388 (7)
C4—H4A0.9300C13—H13A0.9300
C5—C61.402 (6)C14—C151.389 (6)
C5—H5A0.9300C14—H14A0.9300
C6—C71.496 (6)C15—H15A0.9300
C7—C81.487 (6)
C2—C1—C6120.4 (4)C7—C8—H8A119.6
C2—C1—H1A119.8C8—C9—C10127.9 (4)
C6—C1—H1A119.8C8—C9—H9A116.0
C3—C2—C1119.2 (4)C10—C9—H9A116.0
C3—C2—H2A120.4C11—C10—C15119.0 (4)
C1—C2—H2A120.4C11—C10—C9118.8 (4)
C2—C3—C4121.8 (4)C15—C10—C9122.1 (4)
C2—C3—Br1118.5 (3)C12—C11—C10120.3 (4)
C4—C3—Br1119.7 (3)C12—C11—H11A119.8
C5—C4—C3118.5 (4)C10—C11—H11A119.8
C5—C4—H4A120.8C11—C12—C13121.3 (4)
C3—C4—H4A120.8C11—C12—Br2118.6 (3)
C4—C5—C6120.5 (4)C13—C12—Br2120.1 (3)
C4—C5—H5A119.8C14—C13—C12118.5 (4)
C6—C5—H5A119.8C14—C13—H13A120.7
C1—C6—C5119.5 (4)C12—C13—H13A120.7
C1—C6—C7122.1 (4)C13—C14—C15121.1 (4)
C5—C6—C7118.4 (4)C13—C14—H14A119.5
O1—C7—C8121.6 (4)C15—C14—H14A119.5
O1—C7—C6120.8 (4)C14—C15—C10119.8 (4)
C8—C7—C6117.7 (4)C14—C15—H15A120.1
C9—C8—C7120.7 (4)C10—C15—H15A120.1
C9—C8—H8A119.6
C6—C1—C2—C33.5 (6)C6—C7—C8—C9170.5 (4)
C1—C2—C3—C44.7 (7)C7—C8—C9—C10176.0 (4)
C1—C2—C3—Br1175.1 (3)C8—C9—C10—C11168.7 (5)
C2—C3—C4—C53.1 (7)C8—C9—C10—C1514.3 (7)
Br1—C3—C4—C5176.8 (3)C15—C10—C11—C121.6 (6)
C3—C4—C5—C60.2 (6)C9—C10—C11—C12175.4 (4)
C2—C1—C6—C50.8 (6)C10—C11—C12—C131.6 (7)
C2—C1—C6—C7179.2 (4)C10—C11—C12—Br2176.9 (3)
C4—C5—C6—C10.9 (6)C11—C12—C13—C141.0 (7)
C4—C5—C6—C7177.6 (4)Br2—C12—C13—C14177.5 (3)
C1—C6—C7—O1154.9 (4)C12—C13—C14—C150.5 (7)
C5—C6—C7—O126.7 (6)C13—C14—C15—C100.5 (7)
C1—C6—C7—C826.2 (6)C11—C10—C15—C141.1 (7)
C5—C6—C7—C8152.2 (4)C9—C10—C15—C14175.8 (4)
O1—C7—C8—C910.6 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O10.932.482.812 (5)101
C2—H2A···Cg2i0.932.753.428 (5)131
C5—H5A···Cg2ii0.932.693.342 (5)127
C11—H11A···Cg1iii0.932.883.568 (5)132
C14—H14A···Cg1iv0.932.693.373 (5)131
Symmetry codes: (i) x+2, y, z+2; (ii) x+1, y, z+1; (iii) x+2, y, z+1; (iv) x+1, y, z+2.
 

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