1,3-Bis(4-bromo­phen­yl)prop-2-en-1-one

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.

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

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Computing details

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

Crystal data

C15H10Br2O	F(000) = 712
Mr = 366.05	Dx = 1.900 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4415 reflections
a = 15.7504 (5) Å	θ = 1.3–32.5°
b = 13.9442 (5) Å	µ = 6.32 mm^−1
c = 5.8289 (2) Å	T = 100 K
β = 92.034 (2)°	Block, yellow
V = 1279.38 (8) Å^3	0.49 × 0.22 × 0.19 mm
Z = 4

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	4614 independent reflections
Radiation source: fine-focus sealed tube	3185 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 8.33 pixels mm^-1	θmax = 32.5°, θmin = 1.3°
ω scans	h = −23→21
Absorption correction: multi-scan (SADABS, Bruker 2005)	k = −21→18
Tmin = 0.127, Tmax = 0.301	l = −8→8
14888 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0551P)^2] where P = (Fo^2 + 2Fc^2)/3
4614 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.67 e Å^−3
0 restraints	Δρmin = −0.78 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.02210 (2)	0.64430 (2)	0.23815 (5)	0.02359 (10)
Br2	0.86687 (2)	0.62840 (2)	0.75167 (6)	0.02553 (10)
O1	0.47252 (16)	0.62464 (18)	1.2039 (4)	0.0266 (5)
C1	0.6058 (2)	0.5923 (2)	0.7204 (5)	0.0198 (6)
H1A	0.5651	0.5712	0.6125	0.024*
C2	0.6913 (2)	0.5904 (2)	0.6665 (5)	0.0207 (6)
H2A	0.7080	0.5673	0.5254	0.025*
C3	0.75116 (19)	0.6240 (2)	0.8287 (5)	0.0193 (6)
C4	0.7279 (2)	0.6561 (2)	1.0429 (5)	0.0186 (6)
H4A	0.7689	0.6771	1.1502	0.022*
C5	0.6425 (2)	0.6562 (2)	1.0946 (5)	0.0190 (6)
H5A	0.6264	0.6772	1.2381	0.023*
C6	0.5803 (2)	0.6252 (2)	0.9331 (5)	0.0180 (6)
C7	0.4903 (2)	0.6251 (2)	0.9998 (5)	0.0193 (6)
C8	0.4230 (2)	0.6266 (2)	0.8157 (5)	0.0208 (6)
H8A	0.4368	0.6428	0.6668	0.025*
C9	0.3424 (2)	0.6049 (2)	0.8617 (5)	0.0193 (6)
H9A	0.3327	0.5837	1.0098	0.023*
C10	0.26827 (19)	0.6108 (2)	0.7055 (5)	0.0177 (6)
C11	0.18948 (19)	0.5785 (2)	0.7794 (5)	0.0187 (6)
H11A	0.1864	0.5506	0.9238	0.022*
C12	0.1162 (2)	0.5872 (2)	0.6428 (5)	0.0198 (6)
H12A	0.0644	0.5651	0.6933	0.024*
C13	0.1218 (2)	0.6298 (2)	0.4284 (5)	0.0184 (6)
C14	0.1990 (2)	0.6623 (2)	0.3500 (5)	0.0190 (6)
H14A	0.2014	0.6909	0.2063	0.023*
C15	0.2714 (2)	0.6521 (2)	0.4841 (5)	0.0179 (6)
H15A	0.3232	0.6725	0.4295	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.01939 (17)	0.03140 (19)	0.01969 (15)	−0.00055 (13)	−0.00326 (11)	0.00215 (12)
Br2	0.02020 (18)	0.02900 (18)	0.02752 (17)	0.00196 (13)	0.00285 (12)	−0.00024 (13)
O1	0.0266 (13)	0.0384 (14)	0.0149 (10)	−0.0019 (10)	0.0017 (9)	0.0016 (9)
C1	0.0231 (15)	0.0207 (15)	0.0153 (13)	−0.0011 (13)	−0.0038 (11)	0.0014 (11)
C2	0.0246 (16)	0.0205 (15)	0.0169 (13)	0.0023 (13)	0.0014 (12)	0.0010 (11)
C3	0.0180 (15)	0.0193 (14)	0.0208 (13)	0.0028 (12)	0.0027 (11)	0.0022 (11)
C4	0.0194 (15)	0.0201 (14)	0.0160 (13)	0.0014 (12)	−0.0032 (11)	−0.0009 (11)
C5	0.0210 (16)	0.0184 (14)	0.0173 (13)	0.0004 (12)	−0.0012 (11)	−0.0025 (11)
C6	0.0210 (15)	0.0172 (14)	0.0158 (13)	−0.0010 (12)	−0.0020 (11)	0.0017 (10)
C7	0.0215 (16)	0.0203 (14)	0.0160 (13)	−0.0003 (12)	−0.0006 (11)	−0.0006 (11)
C8	0.0206 (16)	0.0238 (16)	0.0178 (13)	0.0000 (13)	−0.0004 (11)	0.0028 (11)
C9	0.0224 (16)	0.0172 (14)	0.0181 (13)	0.0011 (12)	−0.0007 (11)	0.0010 (11)
C10	0.0185 (15)	0.0199 (14)	0.0147 (13)	0.0009 (12)	0.0001 (11)	−0.0011 (11)
C11	0.0238 (16)	0.0202 (14)	0.0121 (12)	−0.0013 (12)	0.0002 (11)	0.0037 (10)
C12	0.0228 (16)	0.0205 (15)	0.0162 (13)	−0.0034 (13)	0.0004 (11)	0.0009 (11)
C13	0.0184 (15)	0.0193 (14)	0.0173 (13)	0.0022 (12)	−0.0016 (11)	−0.0004 (11)
C14	0.0217 (16)	0.0200 (14)	0.0153 (13)	−0.0024 (12)	−0.0010 (11)	−0.0001 (11)
C15	0.0211 (15)	0.0180 (14)	0.0149 (12)	−0.0028 (12)	0.0033 (11)	−0.0017 (10)

Geometric parameters (Å, º)

Br1—C13	1.901 (3)	C8—C9	1.342 (4)
Br2—C3	1.893 (3)	C8—H8A	0.9300
O1—C7	1.232 (3)	C9—C10	1.457 (4)
C1—C2	1.394 (4)	C9—H9A	0.9300
C1—C6	1.395 (4)	C10—C11	1.402 (4)
C1—H1A	0.9300	C10—C15	1.415 (4)
C2—C3	1.392 (5)	C11—C12	1.384 (4)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.388 (4)	C12—C13	1.389 (4)
C4—C5	1.389 (4)	C12—H12A	0.9300
C4—H4A	0.9300	C13—C14	1.390 (4)
C5—C6	1.403 (4)	C14—C15	1.367 (4)
C5—H5A	0.9300	C14—H14A	0.9300
C6—C7	1.484 (4)	C15—H15A	0.9300
C7—C8	1.480 (5)
C2—C1—C6	121.2 (3)	C7—C8—H8A	119.7
C2—C1—H1A	119.4	C8—C9—C10	127.3 (3)
C6—C1—H1A	119.4	C8—C9—H9A	116.4
C3—C2—C1	118.5 (3)	C10—C9—H9A	116.4
C3—C2—H2A	120.8	C11—C10—C15	118.1 (3)
C1—C2—H2A	120.8	C11—C10—C9	119.2 (3)
C4—C3—C2	121.7 (3)	C15—C10—C9	122.6 (3)
C4—C3—Br2	119.3 (2)	C12—C11—C10	121.6 (3)
C2—C3—Br2	118.9 (2)	C12—C11—H11A	119.2
C3—C4—C5	119.0 (3)	C10—C11—H11A	119.2
C3—C4—H4A	120.5	C11—C12—C13	118.5 (3)
C5—C4—H4A	120.5	C11—C12—H12A	120.7
C4—C5—C6	120.8 (3)	C13—C12—H12A	120.7
C4—C5—H5A	119.6	C12—C13—C14	121.3 (3)
C6—C5—H5A	119.6	C12—C13—Br1	119.5 (2)
C1—C6—C5	118.8 (3)	C14—C13—Br1	119.2 (2)
C1—C6—C7	122.7 (3)	C15—C14—C13	120.0 (3)
C5—C6—C7	118.4 (3)	C15—C14—H14A	120.0
O1—C7—C8	121.3 (3)	C13—C14—H14A	120.0
O1—C7—C6	120.3 (3)	C14—C15—C10	120.6 (3)
C8—C7—C6	118.4 (2)	C14—C15—H15A	119.7
C9—C8—C7	120.6 (3)	C10—C15—H15A	119.7
C9—C8—H8A	119.7
C6—C1—C2—C3	−1.2 (4)	C6—C7—C8—C9	164.8 (3)
C1—C2—C3—C4	2.0 (4)	C7—C8—C9—C10	174.5 (3)
C1—C2—C3—Br2	−176.6 (2)	C8—C9—C10—C11	175.5 (3)
C2—C3—C4—C5	−1.2 (4)	C8—C9—C10—C15	−7.5 (5)
Br2—C3—C4—C5	177.4 (2)	C15—C10—C11—C12	−0.6 (4)
C3—C4—C5—C6	−0.4 (4)	C9—C10—C11—C12	176.4 (3)
C2—C1—C6—C5	−0.4 (4)	C10—C11—C12—C13	−0.5 (4)
C2—C1—C6—C7	−177.8 (3)	C11—C12—C13—C14	0.6 (4)
C4—C5—C6—C1	1.2 (4)	C11—C12—C13—Br1	−179.2 (2)
C4—C5—C6—C7	178.7 (3)	C12—C13—C14—C15	0.4 (4)
C1—C6—C7—O1	156.7 (3)	Br1—C13—C14—C15	−179.8 (2)
C5—C6—C7—O1	−20.8 (4)	C13—C14—C15—C10	−1.6 (4)
C1—C6—C7—C8	−24.1 (4)	C11—C10—C15—C14	1.7 (4)
C5—C6—C7—C8	158.5 (3)	C9—C10—C15—C14	−175.3 (3)
O1—C7—C8—C9	−15.9 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1	0.93	2.51	2.822 (4)	100
C5—H5A···Cg1^i	0.93	2.96	3.504 (3)	119
C9—H9A···Cg1^ii	0.93	2.97	3.532 (3)	121
C14—H14A···Cg2^iii	0.93	2.76	3.459 (3)	132

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x+1, −y+1, −z+2; (iii) x, −y+3/2, z−1/2.