Download citation
Download citation
link to html
The enone group and the benzene rings of the title compound, C15H10Br2O, are each planar. The crystal packing is stabillized by weak inter­molecular C—H...π inter­actions involving both aromatic rings; the mol­ecules are stacked along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806008841/sj2015sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806008841/sj2015Isup2.hkl
Contains datablock I

CCDC reference: 605183

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.038
  • wR factor = 0.112
  • Data-to-parameter ratio = 28.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H5A .. CG1 .. 2.96 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9A .. CG1 .. 2.97 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 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 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: H.K. Fun and I.A. Razak are supervisors of Shea-Lin Ng whereas S. M. Dharmaprakash is the supervisor of P. S. Patil and Venkataraya Shettigaris in this collaborative pulication. Mangalore University is involved in the extraction and synthesis of the title compound and USM is involved in the structure determination. All parties are involved in writing up the manuscript.

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

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).

1,3-Bis(4-bromophenyl)prop-2-en-1-one top
Crystal data top
C15H10Br2OF(000) = 712
Mr = 366.05Dx = 1.900 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4415 reflections
a = 15.7504 (5) Åθ = 1.3–32.5°
b = 13.9442 (5) ŵ = 6.32 mm1
c = 5.8289 (2) ÅT = 100 K
β = 92.034 (2)°Block, yellow
V = 1279.38 (8) Å30.49 × 0.22 × 0.19 mm
Z = 4
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
4614 independent reflections
Radiation source: fine-focus sealed tube3185 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 8.33 pixels mm-1θmax = 32.5°, θmin = 1.3°
ω scansh = 2321
Absorption correction: multi-scan
(SADABS, Bruker 2005)
k = 2118
Tmin = 0.127, Tmax = 0.301l = 88
14888 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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0551P)2]
where P = (Fo2 + 2Fc2)/3
4614 reflections(Δ/σ)max = 0.001
163 parametersΔρmax = 0.67 e Å3
0 restraintsΔρmin = 0.78 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
Br10.02210 (2)0.64430 (2)0.23815 (5)0.02359 (10)
Br20.86687 (2)0.62840 (2)0.75167 (6)0.02553 (10)
O10.47252 (16)0.62464 (18)1.2039 (4)0.0266 (5)
C10.6058 (2)0.5923 (2)0.7204 (5)0.0198 (6)
H1A0.56510.57120.61250.024*
C20.6913 (2)0.5904 (2)0.6665 (5)0.0207 (6)
H2A0.70800.56730.52540.025*
C30.75116 (19)0.6240 (2)0.8287 (5)0.0193 (6)
C40.7279 (2)0.6561 (2)1.0429 (5)0.0186 (6)
H4A0.76890.67711.15020.022*
C50.6425 (2)0.6562 (2)1.0946 (5)0.0190 (6)
H5A0.62640.67721.23810.023*
C60.5803 (2)0.6252 (2)0.9331 (5)0.0180 (6)
C70.4903 (2)0.6251 (2)0.9998 (5)0.0193 (6)
C80.4230 (2)0.6266 (2)0.8157 (5)0.0208 (6)
H8A0.43680.64280.66680.025*
C90.3424 (2)0.6049 (2)0.8617 (5)0.0193 (6)
H9A0.33270.58371.00980.023*
C100.26827 (19)0.6108 (2)0.7055 (5)0.0177 (6)
C110.18948 (19)0.5785 (2)0.7794 (5)0.0187 (6)
H11A0.18640.55060.92380.022*
C120.1162 (2)0.5872 (2)0.6428 (5)0.0198 (6)
H12A0.06440.56510.69330.024*
C130.1218 (2)0.6298 (2)0.4284 (5)0.0184 (6)
C140.1990 (2)0.6623 (2)0.3500 (5)0.0190 (6)
H14A0.20140.69090.20630.023*
C150.2714 (2)0.6521 (2)0.4841 (5)0.0179 (6)
H15A0.32320.67250.42950.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.01939 (17)0.03140 (19)0.01969 (15)0.00055 (13)0.00326 (11)0.00215 (12)
Br20.02020 (18)0.02900 (18)0.02752 (17)0.00196 (13)0.00285 (12)0.00024 (13)
O10.0266 (13)0.0384 (14)0.0149 (10)0.0019 (10)0.0017 (9)0.0016 (9)
C10.0231 (15)0.0207 (15)0.0153 (13)0.0011 (13)0.0038 (11)0.0014 (11)
C20.0246 (16)0.0205 (15)0.0169 (13)0.0023 (13)0.0014 (12)0.0010 (11)
C30.0180 (15)0.0193 (14)0.0208 (13)0.0028 (12)0.0027 (11)0.0022 (11)
C40.0194 (15)0.0201 (14)0.0160 (13)0.0014 (12)0.0032 (11)0.0009 (11)
C50.0210 (16)0.0184 (14)0.0173 (13)0.0004 (12)0.0012 (11)0.0025 (11)
C60.0210 (15)0.0172 (14)0.0158 (13)0.0010 (12)0.0020 (11)0.0017 (10)
C70.0215 (16)0.0203 (14)0.0160 (13)0.0003 (12)0.0006 (11)0.0006 (11)
C80.0206 (16)0.0238 (16)0.0178 (13)0.0000 (13)0.0004 (11)0.0028 (11)
C90.0224 (16)0.0172 (14)0.0181 (13)0.0011 (12)0.0007 (11)0.0010 (11)
C100.0185 (15)0.0199 (14)0.0147 (13)0.0009 (12)0.0001 (11)0.0011 (11)
C110.0238 (16)0.0202 (14)0.0121 (12)0.0013 (12)0.0002 (11)0.0037 (10)
C120.0228 (16)0.0205 (15)0.0162 (13)0.0034 (13)0.0004 (11)0.0009 (11)
C130.0184 (15)0.0193 (14)0.0173 (13)0.0022 (12)0.0016 (11)0.0004 (11)
C140.0217 (16)0.0200 (14)0.0153 (13)0.0024 (12)0.0010 (11)0.0001 (11)
C150.0211 (15)0.0180 (14)0.0149 (12)0.0028 (12)0.0033 (11)0.0017 (10)
Geometric parameters (Å, º) top
Br1—C131.901 (3)C8—C91.342 (4)
Br2—C31.893 (3)C8—H8A0.9300
O1—C71.232 (3)C9—C101.457 (4)
C1—C21.394 (4)C9—H9A0.9300
C1—C61.395 (4)C10—C111.402 (4)
C1—H1A0.9300C10—C151.415 (4)
C2—C31.392 (5)C11—C121.384 (4)
C2—H2A0.9300C11—H11A0.9300
C3—C41.388 (4)C12—C131.389 (4)
C4—C51.389 (4)C12—H12A0.9300
C4—H4A0.9300C13—C141.390 (4)
C5—C61.403 (4)C14—C151.367 (4)
C5—H5A0.9300C14—H14A0.9300
C6—C71.484 (4)C15—H15A0.9300
C7—C81.480 (5)
C2—C1—C6121.2 (3)C7—C8—H8A119.7
C2—C1—H1A119.4C8—C9—C10127.3 (3)
C6—C1—H1A119.4C8—C9—H9A116.4
C3—C2—C1118.5 (3)C10—C9—H9A116.4
C3—C2—H2A120.8C11—C10—C15118.1 (3)
C1—C2—H2A120.8C11—C10—C9119.2 (3)
C4—C3—C2121.7 (3)C15—C10—C9122.6 (3)
C4—C3—Br2119.3 (2)C12—C11—C10121.6 (3)
C2—C3—Br2118.9 (2)C12—C11—H11A119.2
C3—C4—C5119.0 (3)C10—C11—H11A119.2
C3—C4—H4A120.5C11—C12—C13118.5 (3)
C5—C4—H4A120.5C11—C12—H12A120.7
C4—C5—C6120.8 (3)C13—C12—H12A120.7
C4—C5—H5A119.6C12—C13—C14121.3 (3)
C6—C5—H5A119.6C12—C13—Br1119.5 (2)
C1—C6—C5118.8 (3)C14—C13—Br1119.2 (2)
C1—C6—C7122.7 (3)C15—C14—C13120.0 (3)
C5—C6—C7118.4 (3)C15—C14—H14A120.0
O1—C7—C8121.3 (3)C13—C14—H14A120.0
O1—C7—C6120.3 (3)C14—C15—C10120.6 (3)
C8—C7—C6118.4 (2)C14—C15—H15A119.7
C9—C8—C7120.6 (3)C10—C15—H15A119.7
C9—C8—H8A119.7
C6—C1—C2—C31.2 (4)C6—C7—C8—C9164.8 (3)
C1—C2—C3—C42.0 (4)C7—C8—C9—C10174.5 (3)
C1—C2—C3—Br2176.6 (2)C8—C9—C10—C11175.5 (3)
C2—C3—C4—C51.2 (4)C8—C9—C10—C157.5 (5)
Br2—C3—C4—C5177.4 (2)C15—C10—C11—C120.6 (4)
C3—C4—C5—C60.4 (4)C9—C10—C11—C12176.4 (3)
C2—C1—C6—C50.4 (4)C10—C11—C12—C130.5 (4)
C2—C1—C6—C7177.8 (3)C11—C12—C13—C140.6 (4)
C4—C5—C6—C11.2 (4)C11—C12—C13—Br1179.2 (2)
C4—C5—C6—C7178.7 (3)C12—C13—C14—C150.4 (4)
C1—C6—C7—O1156.7 (3)Br1—C13—C14—C15179.8 (2)
C5—C6—C7—O120.8 (4)C13—C14—C15—C101.6 (4)
C1—C6—C7—C824.1 (4)C11—C10—C15—C141.7 (4)
C5—C6—C7—C8158.5 (3)C9—C10—C15—C14175.3 (3)
O1—C7—C8—C915.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O10.932.512.822 (4)100
C5—H5A···Cg1i0.932.963.504 (3)119
C9—H9A···Cg1ii0.932.973.532 (3)121
C14—H14A···Cg2iii0.932.763.459 (3)132
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x+1, y+1, z+2; (iii) x, y+3/2, z1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds