(2E)-1-(3-Bromo­phen­yl)-3-(4-chloro­phen­yl)prop-2-en-1-one

In the title compound, C₁₅H₁₀BrClO, the dihedral angle between the benzene rings is 46.70 (5)°. The crystal structure is stabilized by Br...Br and Cl...Cl contacts and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.032
• wR factor = 0.096
• Data-to-parameter ratio = 33.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         200 Deg.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  Br1     ..       3.54 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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


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 Jeannie B.-J. Teh whereas S. M. Dharmaprakash is supervisor of P. S. Patil and Y. E. Satheesh 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).

(2E)-1-(3-bromophenyl)-3-(4-chlorophenyl)prop-2-en-1-one

Crystal data

C15H10BrClO	Z = 2
Mr = 321.59	F(000) = 320
Triclinic, P1	Dx = 1.711 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9155 (2) Å	Cell parameters from 7892 reflections
b = 7.2642 (2) Å	θ = 1.4–35.0°
c = 14.6629 (5) Å	µ = 3.49 mm^−1
α = 86.452 (2)°	T = 100 K
β = 83.241 (2)°	Block, yellow
γ = 87.863 (2)°	0.46 × 0.30 × 0.28 mm
V = 624.22 (3) Å^3

Data collection

Bruker SMART APEX2 CCD diffractometer	5457 independent reflections
Radiation source: fine-focus sealed tube	4586 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 8.33 pixels mm^-1	θmax = 35.0°, θmin = 1.4°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −11→11
Tmin = 0.285, Tmax = 0.370	l = −23→23
17416 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0478P)^2 + 0.385P] where P = (Fo^2 + 2Fc^2)/3
5457 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 1.06 e Å^−3
0 restraints	Δρmin = −0.63 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	0.80012 (3)	0.39433 (3)	−0.415341 (12)	0.02024 (6)
Cl1	−0.30162 (8)	−0.04626 (7)	0.41489 (3)	0.02169 (9)
O1	0.7337 (2)	0.2822 (2)	−0.04076 (10)	0.0217 (3)
C1	0.6370 (3)	0.3467 (2)	−0.22493 (11)	0.0154 (3)
H1A	0.7811	0.2956	−0.2184	0.018*
C2	0.5799 (3)	0.4113 (2)	−0.31093 (12)	0.0165 (3)
C3	0.3678 (3)	0.4912 (3)	−0.32221 (12)	0.0182 (3)
H3A	0.3333	0.5342	−0.3802	0.022*
C4	0.2079 (3)	0.5061 (3)	−0.24579 (13)	0.0182 (3)
H4A	0.0658	0.5610	−0.2525	0.022*
C5	0.2576 (3)	0.4400 (2)	−0.15933 (12)	0.0171 (3)
H5A	0.1483	0.4487	−0.1086	0.021*
C6	0.4727 (3)	0.3603 (2)	−0.14866 (11)	0.0156 (3)
C7	0.5344 (3)	0.2908 (2)	−0.05638 (12)	0.0165 (3)
C8	0.3462 (3)	0.2311 (3)	0.01340 (12)	0.0178 (3)
H8A	0.2015	0.2187	−0.0039	0.021*
C9	0.3822 (3)	0.1948 (2)	0.10137 (12)	0.0163 (3)
H9A	0.5287	0.2109	0.1160	0.020*
C10	0.2126 (3)	0.1321 (2)	0.17650 (11)	0.0152 (3)
C11	0.0051 (3)	0.0594 (2)	0.16118 (12)	0.0164 (3)
H11A	−0.0280	0.0497	0.1012	0.020*
C12	−0.1514 (3)	0.0019 (2)	0.23424 (12)	0.0167 (3)
H12A	−0.2877	−0.0482	0.2237	0.020*
C13	−0.1017 (3)	0.0202 (2)	0.32399 (12)	0.0167 (3)
C14	0.1022 (3)	0.0901 (3)	0.34143 (12)	0.0178 (3)
H14A	0.1337	0.1008	0.4015	0.021*
C15	0.2592 (3)	0.1441 (2)	0.26723 (12)	0.0162 (3)
H15A	0.3981	0.1890	0.2782	0.019*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.01950 (9)	0.02548 (10)	0.01472 (8)	−0.00018 (6)	0.00089 (6)	0.00125 (6)
Cl1	0.01928 (19)	0.0291 (2)	0.01580 (17)	−0.00193 (15)	0.00153 (14)	−0.00025 (15)
O1	0.0162 (6)	0.0293 (7)	0.0192 (6)	−0.0010 (5)	−0.0023 (5)	0.0014 (5)
C1	0.0146 (7)	0.0160 (7)	0.0157 (6)	−0.0009 (5)	−0.0029 (5)	−0.0001 (5)
C2	0.0167 (7)	0.0172 (7)	0.0152 (6)	−0.0008 (5)	−0.0002 (5)	−0.0001 (5)
C3	0.0184 (7)	0.0186 (8)	0.0180 (7)	−0.0002 (6)	−0.0048 (6)	0.0011 (6)
C4	0.0161 (7)	0.0171 (7)	0.0216 (7)	0.0006 (5)	−0.0038 (6)	−0.0011 (6)
C5	0.0162 (7)	0.0162 (7)	0.0187 (7)	0.0004 (5)	−0.0011 (5)	−0.0021 (5)
C6	0.0164 (7)	0.0153 (7)	0.0151 (6)	−0.0007 (5)	−0.0025 (5)	−0.0007 (5)
C7	0.0172 (7)	0.0167 (7)	0.0156 (7)	−0.0011 (5)	−0.0019 (5)	−0.0015 (5)
C8	0.0172 (7)	0.0198 (8)	0.0161 (7)	−0.0025 (6)	−0.0007 (5)	−0.0006 (6)
C9	0.0166 (7)	0.0153 (7)	0.0167 (7)	0.0002 (5)	−0.0009 (5)	−0.0006 (5)
C10	0.0159 (7)	0.0157 (7)	0.0140 (6)	0.0005 (5)	−0.0021 (5)	−0.0007 (5)
C11	0.0176 (7)	0.0170 (7)	0.0147 (6)	−0.0005 (5)	−0.0021 (5)	−0.0018 (5)
C12	0.0160 (7)	0.0175 (7)	0.0169 (7)	−0.0006 (5)	−0.0017 (5)	−0.0029 (5)
C13	0.0166 (7)	0.0180 (7)	0.0149 (6)	0.0013 (5)	−0.0003 (5)	−0.0005 (5)
C14	0.0191 (7)	0.0208 (8)	0.0139 (6)	0.0017 (6)	−0.0040 (5)	−0.0010 (5)
C15	0.0168 (7)	0.0168 (7)	0.0156 (6)	−0.0004 (5)	−0.0042 (5)	−0.0012 (5)

Geometric parameters (Å, º)

Br1—C2	1.8969 (17)	C8—C9	1.341 (2)
Cl1—C13	1.7321 (18)	C8—H8A	0.9300
O1—C7	1.226 (2)	C9—C10	1.463 (2)
C1—C2	1.393 (2)	C9—H9A	0.9300
C1—C6	1.398 (2)	C10—C15	1.399 (2)
C1—H1A	0.9300	C10—C11	1.402 (2)
C2—C3	1.386 (2)	C11—C12	1.385 (2)
C3—C4	1.386 (3)	C11—H11A	0.9300
C3—H3A	0.9300	C12—C13	1.397 (2)
C4—C5	1.388 (3)	C12—H12A	0.9300
C4—H4A	0.9300	C13—C14	1.383 (3)
C5—C6	1.400 (2)	C14—C15	1.392 (2)
C5—H5A	0.9300	C14—H14A	0.9300
C6—C7	1.496 (2)	C15—H15A	0.9300
C7—C8	1.479 (2)
C2—C1—C6	118.50 (15)	C7—C8—H8A	119.7
C2—C1—H1A	120.7	C8—C9—C10	126.08 (17)
C6—C1—H1A	120.7	C8—C9—H9A	117.0
C3—C2—C1	121.83 (16)	C10—C9—H9A	117.0
C3—C2—Br1	118.94 (13)	C15—C10—C11	118.55 (16)
C1—C2—Br1	119.22 (13)	C15—C10—C9	118.90 (16)
C4—C3—C2	118.99 (16)	C11—C10—C9	122.55 (15)
C4—C3—H3A	120.5	C12—C11—C10	120.80 (16)
C2—C3—H3A	120.5	C12—C11—H11A	119.6
C3—C4—C5	120.69 (16)	C10—C11—H11A	119.6
C3—C4—H4A	119.7	C11—C12—C13	119.12 (16)
C5—C4—H4A	119.7	C11—C12—H12A	120.4
C4—C5—C6	119.84 (16)	C13—C12—H12A	120.4
C4—C5—H5A	120.1	C14—C13—C12	121.49 (16)
C6—C5—H5A	120.1	C14—C13—Cl1	119.71 (13)
C1—C6—C5	120.13 (15)	C12—C13—Cl1	118.80 (14)
C1—C6—C7	118.40 (15)	C13—C14—C15	118.63 (16)
C5—C6—C7	121.46 (15)	C13—C14—H14A	120.7
O1—C7—C8	122.18 (16)	C15—C14—H14A	120.7
O1—C7—C6	120.63 (16)	C14—C15—C10	121.39 (16)
C8—C7—C6	117.18 (15)	C14—C15—H15A	119.3
C9—C8—C7	120.63 (16)	C10—C15—H15A	119.3
C9—C8—H8A	119.7
C6—C1—C2—C3	1.3 (3)	C6—C7—C8—C9	−169.51 (17)
C6—C1—C2—Br1	179.97 (13)	C7—C8—C9—C10	−178.94 (17)
C1—C2—C3—C4	−0.4 (3)	C8—C9—C10—C15	−164.21 (18)
Br1—C2—C3—C4	−179.08 (14)	C8—C9—C10—C11	16.1 (3)
C2—C3—C4—C5	−0.8 (3)	C15—C10—C11—C12	0.5 (3)
C3—C4—C5—C6	1.1 (3)	C9—C10—C11—C12	−179.85 (16)
C2—C1—C6—C5	−1.0 (3)	C10—C11—C12—C13	1.1 (3)
C2—C1—C6—C7	−179.98 (16)	C11—C12—C13—C14	−1.6 (3)
C4—C5—C6—C1	−0.2 (3)	C11—C12—C13—Cl1	178.27 (14)
C4—C5—C6—C7	178.77 (16)	C12—C13—C14—C15	0.4 (3)
C1—C6—C7—O1	24.7 (3)	Cl1—C13—C14—C15	−179.44 (13)
C5—C6—C7—O1	−154.26 (18)	C13—C14—C15—C10	1.2 (3)
C1—C6—C7—C8	−154.29 (17)	C11—C10—C15—C14	−1.7 (3)
C5—C6—C7—C8	26.7 (2)	C9—C10—C15—C14	178.63 (16)
O1—C7—C8—C9	11.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1	0.93	2.50	2.826 (2)	101
C1—H1A···Cg2^i	0.93	2.87	3.523 (2)	128
C4—H4A···Cg2^ii	0.93	2.72	3.367 (2)	128
C9—H9A···Cg1^iii	0.93	3.30	3.776 (2)	114
C12—H12A···Cg1^iv	0.93	2.87	3.543 (2)	130
C15—H15A···Cg1^iii	0.93	3.04	3.690 (2)	129

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