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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2439.
Published online 2008 November 26. doi:  10.1107/S1600536808038646
PMCID: PMC2959886

2-Bromo-1,3-diphenyl­propan-1,3-dione

Abstract

The title compound, C15H11BrO2, exists as a diketone in which the two benzoyl groups are nearly perpendicular to each other [dihedral angles = 79.9 (1) and 87.4 (1)° in the two independent mol­ecules].

Related literature

The compound is claimed to exist in the enol form as it condenses with 2-amino­thia­zole and 2-mercaptoimidazoline; see: Robert & Panouse (1979 [triangle]). The parent dibenzoyl­methane mol­ecule exists in two modications, as 1,3-diphenyl-1-hydroxy­propen-1-one; see: Kaitner & Meštrović (1993 [triangle]); Ozturk et al. (1997 [triangle]).

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Object name is e-64-o2439-scheme1.jpg

Experimental

Crystal data

  • C15H11BrO2
  • M r = 303.15
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2439-efi1.jpg
  • a = 28.0680 (6) Å
  • b = 5.6508 (1) Å
  • c = 15.3741 (3) Å
  • V = 2438.43 (8) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 3.36 mm−1
  • T = 100 (2) K
  • 0.27 × 0.20 × 0.06 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.464, T max = 0.824
  • 21610 measured reflections
  • 5562 independent reflections
  • 4774 reflections with I > 2σ(I)
  • R int = 0.060

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.086
  • S = 0.99
  • 5562 reflections
  • 325 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.76 e Å−3
  • Δρmin = −0.52 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2644 Fridel pairs
  • Flack parameter: −0.002 (9)

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038646/pk2135sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038646/pk2135Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

The commerically available compound was recrystallized from toluene.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 Å) and were included in the refinement using a riding model approximation, with U(H) set to 1.2U(C).

The (200) reflection was omitted.

Figures

Fig. 1.
Thermal ellipsoid (Barbour, 2001) plot of the two independent molecules of C15H11BrO2 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C15H11BrO2F000 = 1216
Mr = 303.15Dx = 1.652 Mg m3
Orthorhombic, Pca21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 4583 reflections
a = 28.0680 (6) Åθ = 2.6–25.4º
b = 5.6508 (1) ŵ = 3.36 mm1
c = 15.3741 (3) ÅT = 100 (2) K
V = 2438.43 (8) Å3Plate, colorless
Z = 80.27 × 0.20 × 0.06 mm

Data collection

Bruker SMART APEX diffractometer5562 independent reflections
Radiation source: fine-focus sealed tube4774 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.060
T = 173(2) Kθmax = 27.5º
ω scansθmin = 2.0º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)h = −36→35
Tmin = 0.464, Tmax = 0.824k = −7→7
21610 measured reflectionsl = −19→19

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.037  w = 1/[σ2(Fo2) + (0.0511P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.087(Δ/σ)max = 0.001
S = 0.99Δρmax = 0.76 e Å3
5562 reflectionsΔρmin = −0.52 e Å3
325 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), 2644 Fridel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.002 (9)
Secondary atom site location: difference Fourier map

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Br10.264659 (13)0.21340 (7)0.50000 (3)0.01660 (9)
Br20.355868 (14)1.36089 (7)0.23689 (3)0.01981 (10)
O10.18018 (11)−0.0909 (5)0.52553 (18)0.0212 (7)
O20.17207 (11)0.1525 (5)0.33248 (18)0.0181 (6)
O30.44667 (12)1.6039 (6)0.1914 (2)0.0312 (8)
O40.44450 (11)1.4517 (5)0.39763 (19)0.0216 (7)
C10.11351 (15)0.1585 (6)0.5074 (3)0.0147 (8)
C20.09476 (15)0.3667 (8)0.4735 (3)0.0183 (9)
H20.11530.48460.45050.022*
C30.04576 (15)0.4012 (8)0.4733 (3)0.0188 (9)
H30.03300.54110.44820.023*
C40.01566 (16)0.2367 (7)0.5086 (3)0.0233 (10)
H4−0.01780.26230.50800.028*
C50.03430 (16)0.0314 (8)0.5455 (3)0.0208 (9)
H50.0136−0.08180.57110.025*
C60.08317 (16)−0.0077 (8)0.5446 (3)0.0194 (9)
H60.0959−0.14810.56950.023*
C70.16522 (15)0.1006 (7)0.5035 (3)0.0171 (8)
C80.19934 (14)0.2929 (7)0.4686 (3)0.0145 (8)
H80.19060.45050.49360.017*
C90.19594 (15)0.3008 (7)0.3688 (3)0.0150 (8)
C100.22242 (14)0.4836 (7)0.3189 (2)0.0138 (8)
C110.22560 (13)0.4551 (7)0.2283 (3)0.0165 (8)
H110.21210.31960.20130.020*
C120.24831 (16)0.6234 (8)0.1785 (3)0.0168 (9)
H120.25010.60420.11720.020*
C130.26858 (15)0.8212 (8)0.2174 (3)0.0188 (9)
H130.28410.93730.18290.023*
C140.26596 (15)0.8482 (7)0.3067 (3)0.0176 (9)
H140.28000.98300.33340.021*
C150.24308 (15)0.6804 (7)0.3579 (3)0.0153 (8)
H150.24160.70000.41920.018*
C160.39938 (16)1.1076 (8)0.4260 (3)0.0168 (9)
C170.37847 (15)0.9021 (8)0.3946 (3)0.0174 (9)
H170.37850.86900.33410.021*
C180.35758 (18)0.7456 (8)0.4527 (3)0.0198 (10)
H180.34400.60260.43180.024*
C190.3564 (2)0.7951 (9)0.5399 (3)0.0252 (11)
H190.34130.68780.57860.030*
C200.37725 (19)1.0017 (9)0.5725 (3)0.0272 (11)
H200.37691.03410.63310.033*
C210.39847 (16)1.1585 (7)0.5150 (3)0.0214 (10)
H210.41241.30060.53610.026*
C220.42297 (14)1.2851 (8)0.3686 (3)0.0159 (8)
C230.42002 (14)1.2619 (8)0.2686 (3)0.0159 (9)
H230.42561.09420.25050.019*
C240.45729 (14)1.4232 (7)0.2285 (3)0.0187 (8)
C250.50847 (14)1.3574 (7)0.2417 (3)0.0163 (8)
C260.52174 (17)1.1460 (7)0.2826 (3)0.0175 (9)
H260.49801.03400.29850.021*
C270.56937 (15)1.0990 (7)0.3001 (3)0.0170 (9)
H270.57830.95530.32760.020*
C280.60386 (16)1.2646 (8)0.2768 (3)0.0193 (9)
H280.63641.23660.29010.023*
C290.59053 (14)1.4708 (7)0.2339 (3)0.0190 (8)
H290.61411.58090.21590.023*
C300.54305 (15)1.5154 (8)0.2177 (2)0.0179 (9)
H300.53421.65810.18930.022*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.01624 (19)0.01938 (19)0.01417 (16)0.00186 (15)−0.00319 (19)−0.00273 (19)
Br20.01400 (19)0.0249 (2)0.02058 (18)0.00115 (17)−0.0026 (2)−0.00051 (18)
O10.0241 (17)0.0178 (16)0.0216 (15)0.0040 (13)0.0017 (12)0.0053 (11)
O20.0206 (17)0.0167 (16)0.0169 (14)−0.0018 (12)−0.0004 (12)−0.0016 (12)
O30.0200 (18)0.026 (2)0.047 (2)0.0031 (14)−0.0006 (16)0.0203 (16)
O40.0191 (17)0.0190 (16)0.0269 (16)−0.0045 (13)0.0007 (13)−0.0065 (13)
C10.018 (2)0.015 (2)0.0107 (18)0.0009 (14)−0.0032 (17)0.0021 (18)
C20.023 (2)0.016 (2)0.0162 (19)−0.0028 (17)0.0000 (17)−0.0040 (15)
C30.020 (2)0.016 (2)0.021 (2)0.0056 (16)−0.0044 (17)0.0010 (16)
C40.017 (2)0.027 (3)0.025 (2)0.0053 (16)0.001 (2)−0.002 (2)
C50.020 (2)0.027 (3)0.015 (2)−0.0058 (19)0.0001 (17)0.0050 (18)
C60.023 (2)0.017 (2)0.018 (2)−0.0011 (17)0.0024 (18)0.0005 (17)
C70.024 (2)0.018 (2)0.0094 (16)0.0007 (16)0.0012 (18)0.0010 (19)
C80.015 (2)0.015 (2)0.0140 (16)0.0032 (16)0.0006 (15)−0.0054 (16)
C90.016 (2)0.013 (2)0.0155 (18)0.0025 (17)−0.0016 (16)−0.0046 (15)
C100.011 (2)0.014 (2)0.0168 (19)−0.0004 (15)−0.0006 (15)0.0013 (16)
C110.0124 (18)0.018 (2)0.019 (2)−0.0006 (15)−0.0032 (19)0.0013 (18)
C120.022 (2)0.021 (2)0.0079 (17)0.0013 (17)−0.0003 (16)−0.0039 (17)
C130.020 (2)0.016 (2)0.021 (2)−0.0026 (16)0.0036 (17)−0.0006 (16)
C140.018 (2)0.015 (2)0.021 (2)−0.0008 (17)−0.0016 (17)−0.0037 (16)
C150.016 (2)0.016 (2)0.0138 (18)0.0020 (16)−0.0038 (16)−0.0024 (16)
C160.018 (2)0.017 (2)0.0153 (19)0.0037 (17)−0.0010 (17)0.0029 (17)
C170.016 (2)0.021 (2)0.0158 (19)0.0024 (17)−0.0009 (17)0.0000 (17)
C180.014 (2)0.017 (2)0.028 (3)−0.0018 (18)0.000 (2)0.0058 (18)
C190.024 (3)0.026 (3)0.026 (2)0.006 (2)0.007 (2)0.006 (2)
C200.038 (3)0.029 (3)0.014 (2)0.002 (2)−0.0012 (19)0.0036 (18)
C210.026 (2)0.017 (2)0.021 (2)0.0014 (17)−0.0040 (18)−0.0013 (17)
C220.010 (2)0.019 (2)0.0186 (19)0.0059 (17)−0.0013 (16)−0.0006 (17)
C230.008 (2)0.021 (2)0.0192 (19)0.0036 (16)−0.0002 (16)0.0040 (16)
C240.020 (2)0.020 (2)0.016 (2)0.0006 (16)0.000 (2)0.0043 (18)
C250.018 (2)0.0157 (19)0.0155 (18)0.0032 (17)0.004 (2)−0.0018 (17)
C260.024 (2)0.012 (2)0.017 (2)−0.0009 (17)0.0009 (18)−0.0021 (16)
C270.022 (2)0.013 (2)0.0164 (19)0.0042 (16)0.0014 (17)−0.0012 (15)
C280.016 (2)0.023 (2)0.019 (2)0.0013 (17)0.0012 (17)−0.0073 (18)
C290.021 (2)0.018 (2)0.0180 (17)−0.0010 (16)0.003 (2)0.0013 (19)
C300.018 (2)0.017 (2)0.020 (2)0.0005 (16)0.0001 (16)0.0003 (16)

Geometric parameters (Å, °)

Br1—C81.948 (4)C14—C151.389 (6)
Br2—C231.947 (4)C14—H140.9500
O1—C71.209 (5)C15—H150.9500
O2—C91.209 (5)C16—C171.388 (6)
O3—C241.207 (5)C16—C211.398 (6)
O4—C221.204 (5)C16—C221.491 (6)
C1—C21.390 (6)C17—C181.387 (6)
C1—C61.391 (6)C17—H170.9500
C1—C71.489 (6)C18—C191.369 (6)
C2—C31.389 (6)C18—H180.9500
C2—H20.9500C19—C201.399 (7)
C3—C41.369 (6)C19—H190.9500
C3—H30.9500C20—C211.386 (6)
C4—C51.393 (6)C20—H200.9500
C4—H40.9500C21—H210.9500
C5—C61.389 (6)C22—C231.545 (6)
C5—H50.9500C23—C241.518 (6)
C6—H60.9500C23—H231.0000
C7—C81.544 (6)C24—C251.498 (6)
C8—C91.538 (5)C25—C301.370 (6)
C8—H81.0000C25—C261.400 (6)
C9—C101.487 (6)C26—C271.389 (6)
C10—C151.391 (6)C26—H260.9500
C10—C111.405 (6)C27—C281.393 (6)
C11—C121.377 (6)C27—H270.9500
C11—H110.9500C28—C291.390 (6)
C12—C131.390 (6)C28—H280.9500
C12—H120.9500C29—C301.379 (6)
C13—C141.384 (6)C29—H290.9500
C13—H130.9500C30—H300.9500
C2—C1—C6119.6 (4)C17—C16—C21120.3 (4)
C2—C1—C7122.7 (4)C17—C16—C22123.0 (4)
C6—C1—C7117.7 (3)C21—C16—C22116.7 (4)
C3—C2—C1119.7 (4)C18—C17—C16119.3 (4)
C3—C2—H2120.2C18—C17—H17120.4
C1—C2—H2120.2C16—C17—H17120.4
C4—C3—C2121.0 (4)C19—C18—C17120.7 (5)
C4—C3—H3119.5C19—C18—H18119.7
C2—C3—H3119.5C17—C18—H18119.7
C3—C4—C5119.7 (4)C18—C19—C20120.7 (5)
C3—C4—H4120.2C18—C19—H19119.6
C5—C4—H4120.2C20—C19—H19119.6
C6—C5—C4120.0 (4)C21—C20—C19119.0 (4)
C6—C5—H5120.0C21—C20—H20120.5
C4—C5—H5120.0C19—C20—H20120.5
C5—C6—C1120.0 (4)C20—C21—C16120.0 (4)
C5—C6—H6120.0C20—C21—H21120.0
C1—C6—H6120.0C16—C21—H21120.0
O1—C7—C1121.6 (4)O4—C22—C16121.9 (4)
O1—C7—C8120.8 (4)O4—C22—C23117.5 (4)
C1—C7—C8117.6 (3)C16—C22—C23120.5 (4)
C9—C8—C7109.2 (3)C24—C23—C22108.4 (3)
C9—C8—Br1108.2 (3)C24—C23—Br2111.3 (3)
C7—C8—Br1109.6 (3)C22—C23—Br2105.9 (3)
C9—C8—H8110.0C24—C23—H23110.4
C7—C8—H8110.0C22—C23—H23110.4
Br1—C8—H8110.0Br2—C23—H23110.4
O2—C9—C10121.3 (4)O3—C24—C25120.7 (4)
O2—C9—C8118.4 (4)O3—C24—C23122.0 (4)
C10—C9—C8120.3 (3)C25—C24—C23117.2 (3)
C15—C10—C11119.5 (4)C30—C25—C26119.3 (4)
C15—C10—C9122.8 (4)C30—C25—C24118.8 (4)
C11—C10—C9117.7 (3)C26—C25—C24121.8 (4)
C12—C11—C10120.1 (4)C27—C26—C25120.4 (4)
C12—C11—H11120.0C27—C26—H26119.8
C10—C11—H11120.0C25—C26—H26119.8
C11—C12—C13120.4 (4)C26—C27—C28119.4 (4)
C11—C12—H12119.8C26—C27—H27120.3
C13—C12—H12119.8C28—C27—H27120.3
C14—C13—C12119.6 (4)C29—C28—C27119.9 (4)
C14—C13—H13120.2C29—C28—H28120.1
C12—C13—H13120.2C27—C28—H28120.1
C13—C14—C15120.8 (4)C30—C29—C28119.9 (4)
C13—C14—H14119.6C30—C29—H29120.0
C15—C14—H14119.6C28—C29—H29120.0
C14—C15—C10119.6 (4)C25—C30—C29121.1 (4)
C14—C15—H15120.2C25—C30—H30119.4
C10—C15—H15120.2C29—C30—H30119.4
C6—C1—C2—C3−3.2 (6)C21—C16—C17—C18−1.4 (7)
C7—C1—C2—C3175.0 (4)C22—C16—C17—C18179.5 (4)
C1—C2—C3—C42.2 (6)C16—C17—C18—C191.7 (8)
C2—C3—C4—C50.1 (7)C17—C18—C19—C20−1.5 (9)
C3—C4—C5—C6−1.3 (7)C18—C19—C20—C211.1 (8)
C4—C5—C6—C10.3 (6)C19—C20—C21—C16−0.8 (7)
C2—C1—C6—C51.9 (6)C17—C16—C21—C201.0 (7)
C7—C1—C6—C5−176.4 (4)C22—C16—C21—C20−179.9 (4)
C2—C1—C7—O1−172.5 (4)C17—C16—C22—O4−173.4 (4)
C6—C1—C7—O15.7 (6)C21—C16—C22—O47.5 (6)
C2—C1—C7—C86.3 (6)C17—C16—C22—C237.3 (6)
C6—C1—C7—C8−175.4 (4)C21—C16—C22—C23−171.9 (4)
O1—C7—C8—C9101.3 (5)O4—C22—C23—C2415.6 (5)
C1—C7—C8—C9−77.6 (5)C16—C22—C23—C24−165.0 (4)
O1—C7—C8—Br1−17.1 (5)O4—C22—C23—Br2−103.9 (4)
C1—C7—C8—Br1164.1 (3)C16—C22—C23—Br275.4 (4)
C7—C8—C9—O2−6.1 (5)C22—C23—C24—O3−107.7 (5)
Br1—C8—C9—O2113.1 (4)Br2—C23—C24—O38.4 (6)
C7—C8—C9—C10175.3 (3)C22—C23—C24—C2568.5 (5)
Br1—C8—C9—C10−65.5 (4)Br2—C23—C24—C25−175.4 (3)
O2—C9—C10—C15168.2 (4)O3—C24—C25—C305.6 (7)
C8—C9—C10—C15−13.3 (6)C23—C24—C25—C30−170.6 (4)
O2—C9—C10—C11−10.7 (6)O3—C24—C25—C26−178.3 (4)
C8—C9—C10—C11167.9 (4)C23—C24—C25—C265.5 (6)
C15—C10—C11—C12−1.2 (6)C30—C25—C26—C271.2 (6)
C9—C10—C11—C12177.8 (4)C24—C25—C26—C27−174.9 (4)
C10—C11—C12—C130.6 (7)C25—C26—C27—C280.2 (6)
C11—C12—C13—C140.2 (7)C26—C27—C28—C29−2.1 (6)
C12—C13—C14—C15−0.3 (7)C27—C28—C29—C302.6 (7)
C13—C14—C15—C10−0.3 (6)C26—C25—C30—C29−0.7 (7)
C11—C10—C15—C141.0 (6)C24—C25—C30—C29175.5 (4)
C9—C10—C15—C14−177.9 (4)C28—C29—C30—C25−1.2 (7)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2135).

References

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  • Kaitner, B. & Meštrović, E. (1993). Acta Cryst. C49, 1523–1525.
  • Ozturk, S., Akkurt, M. & Ide, S. (1997). Z. Kristallogr.212, 808–810.
  • Robert, J. F. & Panouse, J. J. (1979). J. Heterocycl. Chem.16, 1201–1207.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
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