2,3-Dibromo-1-(2,4-dichloro-5-fluoro­phen­yl)-3-phenyl­propan-1-one

Fun, H.-K.; Jebas, S.R.; Razak, I.A.; Karthikeyan, M.S.; Patil, P.S.; Dharmaprakash, S.M.

doi:10.1107/S1600536808013238

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1039

doi:10.1107/S1600536808013238

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2,3-Dibromo-1-(2,4-dichloro-5-fluorophenyl)-3-phenylpropan-1-one

Hoong-Kun Fun,^a ^* Samuel Robinson Jebas,^a ‡ Ibrahim Abdul Razak,^a M. S. Karthikeyan,^b P. S. Patil ^c and S. M. Dharmaprakash ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bSyngene International Pvt Limited, Plot No. 2 & 3 C, Unit-II, Bommansandra Industrial Area, Banglore 560 099, India, and ^cDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 23 April 2008; accepted 5 May 2008; online 10 May 2008)

In the title compound, C₁₅H₉Br₂Cl₂FO, the dihedral angle between the two aromatic rings is 6.0 (1)°. The dibromoethane fragment of the propan-1-one unit is disordered over two positions, with occupancies of ca 0.83 and 0.17. The crystal structure is stabilized by intermolecular C—H⋯O hydrogen bonds, C—H⋯π interactions, and Br⋯Cl [3.505 (2) and 3.576 (6) Å] and Cl⋯F [3.176 (2) Å] short contacts.

Related literature

For related literature, see: Agrinskaya et al. (1999 ); Patil et al. (2006 ); John Kiran et al. (2007 ). For bond-length data, see: Allen et al. (1987 ). For the preparation, see: Shivarama Holla et al. 2006 ).

Experimental

Crystal data

C₁₅H₉Br₂Cl₂FO
M_r = 454.94
Orthorhombic, P b c a
a = 7.1232 (1) Å
b = 10.0757 (2) Å
c = 43.0262 (7) Å
V = 3088.04 (9) Å³
Z = 8
Mo Kα radiation
μ = 5.60 mm⁻¹
T = 100 (2) K
0.40 × 0.24 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.211, T_max = 0.508 (expected range = 0.190–0.457)
26343 measured reflections
5857 independent reflections
3681 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.089
S = 0.98
5857 reflections
227 parameters
60 restraints
H-atom parameters constrained
Δρ_max = 0.77 e Å⁻³
Δρ_min = −0.76 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	0.95	2.45	3.392 (4)	170
C8—H8⋯O1ⁱ	1.00	2.35	3.336 (4)	169
C11—H11⋯O1ⁱ	0.95	2.29	3.229 (3)	170
C3—H3⋯Cg1ⁱⁱ	0.95	2.96	3.652 (3)	131
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[x-{\script{3\over 2}}, y, -z-{\script{1\over 2}}]$ . Cg1 is the centroid of the C1–C6 benzene ring.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013238/ci2588sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808013238/ci2588Isup2.hkl

checkCIF report

Comment top

Derivatives of chalcone exhibit nonlinear optical (NLO) properties (Agrinskaya et al., 1999; Patil et al., 2006; John Kiran et al., 2007). We report here the crystal structure of the title compound (Fig 1), which crystallizes in a centrosymmetric space group and this precludes the presence of second-order NLO properties.

Bond lengths and angles in the title molecule have normal values (Allen et al., 1987). The dihedral angle between the benzene rings is 6.0 (1)°. The dibromoethane fragment of the propan-1-one unit is diordered over two positions.

The crystal packing is (Fig.2) stabilized by intermolecular C—H···O and weak C—H···π interactions involving the C1–C6 benzene ring (centroid Cg1). In addition, Br2···Cl2(-1+x,y,z) [3.505 (2) Å], Br1A···Cl2(-1+x,y,z) [3.576 (6) Å] and Cl1···F1(1-x,1-y,-z) [3.176 (2) Å] short contacts are oberved in the crystal structure.

Related literature top

For related literature, see: Agrinskaya et al. (1999); Patil et al. (2006); John Kiran et al. (2007). For bond-length data, see: Allen et al. (1987). For the preparation, see: Shivarama Holla et al. 2006). Cg1 is the centroid of the C1–C6 benzene ring.

Experimental top

1-(2,4-Dichloro-5-fluorophenyl)-3-phenylprop-2-en-1-one (1 mmol) was prepared by a literature procedure (Shivarama Holla et al., 2006). To a solution of 1-(2,4-dichloro-5-fluorophenyl)-3-phenylprop-2-en-1-one) (1 mmol) in chloroform (25 ml), bromine (1 mmol) was added slowly with stirring. After the completion of addition the reaction mixture was stirred for 24 h. Excess chloroform was distilled off and crude solid was filtered and dried. The precipitated compound was recrystallized from acetone.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Only the major disorder component is shown.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. Short intra- and intermolecular contacts and hydrogen bonds are shown as dashed lines. Only the major disorder component is shown.

2,3-Dibromo-1-(2,4-dichloro-5-fluorophenyl)-3-phenylpropan-1-one top

Crystal data top

C₁₅H₉Br₂Cl₂FO	F(000) = 1760
M_r = 454.94	D_x = 1.957 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4782 reflections
a = 7.1232 (1) Å	θ = 2.8–28.1°
b = 10.0757 (2) Å	µ = 5.60 mm⁻¹
c = 43.0262 (7) Å	T = 100 K
V = 3088.04 (9) Å³	Block, colourless
Z = 8	0.40 × 0.24 × 0.14 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5857 independent reflections
Radiation source: fine-focus sealed tube	3681 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ϕ and ω scans	θ_max = 33.2°, θ_min = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→8
T_min = 0.211, T_max = 0.508	k = −15→15
26343 measured reflections	l = −52→66

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0309P)² + 2.3603P] where P = (F_o² + 2F_c²)/3
5857 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 0.77 e Å⁻³
60 restraints	Δρ_min = −0.76 e Å⁻³

Crystal data top

C₁₅H₉Br₂Cl₂FO	V = 3088.04 (9) Å³
M_r = 454.94	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.1232 (1) Å	µ = 5.60 mm⁻¹
b = 10.0757 (2) Å	T = 100 K
c = 43.0262 (7) Å	0.40 × 0.24 × 0.14 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5857 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3681 reflections with I > 2σ(I)
T_min = 0.211, T_max = 0.508	R_int = 0.056
26343 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	60 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 0.99	Δρ_max = 0.77 e Å⁻³
5857 reflections	Δρ_min = −0.76 e Å⁻³
227 parameters

Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low–temperature attachment.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.58123 (10)	0.31692 (7)	−0.003788 (15)	0.02739 (16)
Cl2	0.62659 (10)	−0.10513 (7)	0.070833 (16)	0.02701 (16)
F1	0.3512 (3)	0.42768 (15)	0.04559 (4)	0.0314 (4)
O1	0.3888 (3)	−0.05963 (18)	0.12256 (4)	0.0211 (4)
C1	0.0038 (4)	0.0604 (3)	0.21381 (6)	0.0229 (6)
H1	0.0475	−0.0286	0.2151	0.028*
C2	−0.0915 (4)	0.1152 (3)	0.23859 (6)	0.0243 (6)
H2	−0.1147	0.0635	0.2567	0.029*
C3	−0.1533 (4)	0.2449 (3)	0.23723 (7)	0.0273 (6)
H3	−0.2197	0.2822	0.2543	0.033*
C4	−0.1181 (4)	0.3209 (3)	0.21087 (7)	0.0260 (6)
H4	−0.1581	0.4107	0.2100	0.031*
C5	−0.0250 (5)	0.2651 (3)	0.18597 (7)	0.0290 (7)
H5	−0.0025	0.3166	0.1679	0.035*
C6	0.0365 (4)	0.1337 (3)	0.18715 (6)	0.0265 (6)
C9	0.3635 (4)	0.0567 (3)	0.11688 (6)	0.0189 (5)
C10	0.4255 (4)	0.1189 (2)	0.08738 (6)	0.0176 (5)
C11	0.3646 (4)	0.2472 (3)	0.07982 (6)	0.0222 (6)
H11	0.2883	0.2949	0.0941	0.027*
C12	0.4138 (4)	0.3047 (3)	0.05211 (6)	0.0216 (6)
C13	0.5258 (4)	0.2405 (3)	0.03074 (6)	0.0196 (5)
C14	0.5896 (4)	0.1134 (3)	0.03752 (6)	0.0203 (5)
H14	0.6673	0.0677	0.0231	0.024*
C15	0.5397 (4)	0.0535 (2)	0.06529 (6)	0.0185 (5)
Br1	0.4779 (3)	0.1813 (3)	0.17334 (5)	0.0279 (4)	0.834 (6)
Br2	−0.06956 (14)	0.02708 (17)	0.12693 (3)	0.0296 (2)	0.834 (6)
C7	0.1226 (5)	0.0653 (3)	0.15969 (7)	0.0194 (8)	0.834 (6)
H7	0.1772	−0.0209	0.1668	0.023*	0.834 (6)
C8	0.2737 (5)	0.1420 (4)	0.14272 (7)	0.0190 (8)	0.834 (6)
H8	0.2216	0.2261	0.1339	0.023*	0.834 (6)
Br1A	−0.0440 (7)	0.0638 (6)	0.11951 (14)	0.0265 (8)	0.166 (6)
Br2A	0.4743 (16)	0.1862 (16)	0.1704 (2)	0.0222 (16)	0.166 (6)
C7A	0.2193 (14)	0.0999 (16)	0.1700 (3)	0.028 (5)	0.166 (6)
H7A	0.2405	0.0025	0.1728	0.033*	0.166 (6)
C8A	0.2088 (11)	0.1248 (14)	0.1348 (3)	0.015 (4)	0.166 (6)
H8A	0.2190	0.2225	0.1311	0.018*	0.166 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0264 (4)	0.0359 (4)	0.0198 (3)	0.0014 (3)	0.0055 (3)	0.0042 (3)
Cl2	0.0290 (4)	0.0221 (3)	0.0300 (3)	0.0083 (3)	0.0061 (3)	−0.0018 (3)
F1	0.0442 (11)	0.0200 (8)	0.0302 (9)	0.0078 (8)	0.0112 (8)	0.0069 (7)
O1	0.0246 (11)	0.0173 (9)	0.0214 (9)	0.0019 (8)	−0.0011 (8)	−0.0018 (7)
C1	0.0237 (15)	0.0222 (13)	0.0229 (13)	−0.0004 (12)	0.0020 (11)	0.0000 (10)
C2	0.0224 (15)	0.0293 (15)	0.0212 (13)	−0.0056 (12)	0.0026 (11)	0.0010 (11)
C3	0.0224 (16)	0.0323 (16)	0.0271 (15)	−0.0049 (13)	0.0061 (12)	−0.0067 (12)
C4	0.0217 (15)	0.0226 (14)	0.0338 (15)	0.0022 (12)	0.0043 (12)	−0.0038 (12)
C5	0.0381 (19)	0.0219 (14)	0.0270 (15)	0.0049 (13)	0.0102 (13)	0.0045 (11)
C6	0.0322 (18)	0.0248 (14)	0.0226 (13)	0.0052 (13)	0.0082 (12)	0.0013 (11)
C9	0.0190 (14)	0.0173 (12)	0.0203 (13)	−0.0010 (11)	0.0019 (10)	−0.0016 (10)
C10	0.0183 (13)	0.0148 (12)	0.0198 (12)	−0.0012 (10)	0.0021 (10)	−0.0022 (9)
C11	0.0250 (15)	0.0176 (13)	0.0239 (13)	0.0009 (12)	0.0051 (11)	−0.0021 (10)
C12	0.0237 (14)	0.0165 (12)	0.0245 (13)	−0.0004 (11)	0.0011 (11)	0.0019 (10)
C13	0.0182 (14)	0.0249 (14)	0.0158 (12)	−0.0051 (11)	0.0010 (10)	−0.0012 (10)
C14	0.0171 (13)	0.0245 (14)	0.0192 (12)	0.0008 (11)	0.0025 (10)	−0.0054 (10)
C15	0.0144 (13)	0.0165 (12)	0.0244 (13)	−0.0008 (10)	−0.0013 (10)	−0.0034 (10)
Br1	0.0181 (5)	0.0296 (5)	0.0359 (9)	−0.0023 (4)	−0.0012 (5)	−0.0105 (7)
Br2	0.0212 (3)	0.0379 (5)	0.0296 (4)	−0.0013 (3)	−0.0041 (3)	−0.0111 (3)
C7	0.0208 (18)	0.0182 (15)	0.0191 (15)	0.0007 (13)	−0.0027 (13)	−0.0016 (12)
C8	0.022 (2)	0.0175 (16)	0.0173 (17)	−0.0011 (15)	−0.0004 (15)	−0.0024 (12)
Br1A	0.0242 (14)	0.0302 (17)	0.0252 (16)	−0.0071 (12)	−0.0074 (11)	0.0019 (12)
Br2A	0.030 (3)	0.031 (3)	0.0061 (13)	−0.008 (2)	0.0041 (14)	−0.0099 (13)
C7A	0.027 (8)	0.021 (7)	0.035 (8)	−0.010 (6)	−0.010 (6)	0.006 (6)
C8A	0.015 (7)	0.014 (7)	0.016 (7)	−0.005 (6)	−0.007 (5)	0.003 (5)

Geometric parameters (Å, º) top

Cl1—C13	1.719 (3)	C9—C8	1.544 (4)
Cl2—C15	1.731 (3)	C10—C11	1.402 (4)
F1—C12	1.346 (3)	C10—C15	1.414 (4)
O1—C9	1.211 (3)	C11—C12	1.371 (4)
C1—C2	1.380 (4)	C11—H11	0.95
C1—C6	1.384 (4)	C12—C13	1.379 (4)
C1—H1	0.95	C13—C14	1.390 (4)
C2—C3	1.380 (4)	C14—C15	1.385 (4)
C2—H2	0.95	C14—H14	0.95
C3—C4	1.391 (4)	Br1—C8	2.002 (4)
C3—H3	0.95	Br2—C7	2.002 (3)
C4—C5	1.380 (4)	C7—C8	1.513 (4)
C4—H4	0.95	C7—H7	1.00
C5—C6	1.395 (4)	C8—H8	1.00
C5—H5	0.95	Br1A—C8A	2.013 (8)
C6—C7	1.499 (4)	Br2A—C7A	2.014 (8)
C6—C7A	1.536 (9)	C7A—C8A	1.535 (9)
C9—C10	1.483 (4)	C7A—H7A	1.00
C9—C8A	1.509 (9)	C8A—H8A	1.00

C2—C1—C6	120.6 (3)	C12—C13—C14	118.8 (2)
C2—C1—H1	119.7	C12—C13—Cl1	119.9 (2)
C6—C1—H1	119.7	C14—C13—Cl1	121.3 (2)
C1—C2—C3	120.2 (3)	C15—C14—C13	119.9 (2)
C1—C2—H2	119.9	C15—C14—H14	120.0
C3—C2—H2	119.9	C13—C14—H14	120.0
C2—C3—C4	119.9 (3)	C14—C15—C10	121.6 (2)
C2—C3—H3	120.1	C14—C15—Cl2	115.5 (2)
C4—C3—H3	120.1	C10—C15—Cl2	122.9 (2)
C5—C4—C3	119.7 (3)	C6—C7—C8	115.9 (3)
C5—C4—H4	120.2	C6—C7—Br2	111.3 (2)
C3—C4—H4	120.2	C8—C7—Br2	104.2 (2)
C4—C5—C6	120.6 (3)	C6—C7—H7	108.4
C4—C5—H5	119.7	C8—C7—H7	108.4
C6—C5—H5	119.7	Br2—C7—H7	108.4
C1—C6—C5	118.9 (3)	C7—C8—C9	110.9 (3)
C1—C6—C7	118.5 (3)	C7—C8—Br1	107.5 (2)
C5—C6—C7	122.4 (3)	C9—C8—Br1	106.5 (2)
C1—C6—C7A	115.1 (6)	C7—C8—H8	110.6
C5—C6—C7A	117.3 (6)	C9—C8—H8	110.6
O1—C9—C10	122.5 (2)	Br1—C8—H8	110.6
O1—C9—C8A	116.5 (6)	C8A—C7A—C6	113.4 (8)
C10—C9—C8A	117.6 (6)	C8A—C7A—Br2A	89.1 (7)
O1—C9—C8	117.1 (2)	C6—C7A—Br2A	131.6 (9)
C10—C9—C8	120.3 (2)	C8A—C7A—H7A	106.7
C11—C10—C15	116.9 (2)	C6—C7A—H7A	106.7
C11—C10—C9	119.7 (2)	Br2A—C7A—H7A	106.7
C15—C10—C9	123.4 (2)	C9—C8A—C7A	113.2 (8)
C12—C11—C10	120.8 (2)	C9—C8A—Br1A	110.3 (6)
C12—C11—H11	119.6	C7A—C8A—Br1A	108.4 (8)
C10—C11—H11	119.6	C9—C8A—H8A	108.3
F1—C12—C11	119.0 (2)	C7A—C8A—H8A	108.3
F1—C12—C13	119.0 (2)	Br1A—C8A—H8A	108.3
C11—C12—C13	122.0 (2)

C6—C1—C2—C3	−0.9 (4)	C1—C6—C7—C8	−137.6 (3)
C1—C2—C3—C4	−0.5 (4)	C5—C6—C7—C8	47.5 (4)
C2—C3—C4—C5	1.3 (4)	C7A—C6—C7—C8	−44.3 (10)
C3—C4—C5—C6	−0.9 (5)	C1—C6—C7—Br2	103.6 (3)
C2—C1—C6—C5	1.4 (5)	C5—C6—C7—Br2	−71.2 (4)
C2—C1—C6—C7	−173.7 (3)	C7A—C6—C7—Br2	−163.1 (11)
C2—C1—C6—C7A	148.2 (6)	C6—C7—C8—C9	174.9 (3)
C4—C5—C6—C1	−0.5 (5)	Br2—C7—C8—C9	−62.5 (3)
C4—C5—C6—C7	174.4 (3)	C6—C7—C8—Br1	58.9 (3)
C4—C5—C6—C7A	−146.6 (6)	Br2—C7—C8—Br1	−178.49 (17)
O1—C9—C10—C11	169.1 (3)	O1—C9—C8—C7	−38.7 (4)
C8A—C9—C10—C11	10.9 (5)	C10—C9—C8—C7	145.0 (3)
C8—C9—C10—C11	−14.8 (4)	C8A—C9—C8—C7	55.5 (16)
O1—C9—C10—C15	−8.5 (4)	O1—C9—C8—Br1	77.9 (3)
C8A—C9—C10—C15	−166.7 (4)	C10—C9—C8—Br1	−98.3 (3)
C8—C9—C10—C15	167.6 (3)	C8A—C9—C8—Br1	172.1 (18)
C15—C10—C11—C12	0.4 (4)	C1—C6—C7A—C8A	151.0 (9)
C9—C10—C11—C12	−177.3 (3)	C5—C6—C7A—C8A	−61.6 (12)
C10—C11—C12—F1	179.5 (2)	C7—C6—C7A—C8A	46.7 (9)
C10—C11—C12—C13	−0.7 (4)	C1—C6—C7A—Br2A	−97.9 (12)
F1—C12—C13—C14	−179.8 (2)	C5—C6—C7A—Br2A	49.5 (13)
C11—C12—C13—C14	0.3 (4)	C7—C6—C7A—Br2A	157.8 (19)
F1—C12—C13—Cl1	−0.7 (4)	O1—C9—C8A—C7A	49.1 (10)
C11—C12—C13—Cl1	179.4 (2)	C10—C9—C8A—C7A	−151.4 (8)
C12—C13—C14—C15	0.3 (4)	C8—C9—C8A—C7A	−48.3 (12)
Cl1—C13—C14—C15	−178.8 (2)	O1—C9—C8A—Br1A	−72.6 (8)
C13—C14—C15—C10	−0.5 (4)	C10—C9—C8A—Br1A	86.9 (8)
C13—C14—C15—Cl2	179.5 (2)	C8—C9—C8A—Br1A	−170 (2)
C11—C10—C15—C14	0.2 (4)	C6—C7A—C8A—C9	−163.6 (8)
C9—C10—C15—C14	177.8 (3)	Br2A—C7A—C8A—C9	60.7 (10)
C11—C10—C15—Cl2	−179.9 (2)	C6—C7A—C8A—Br1A	−40.8 (13)
C9—C10—C15—Cl2	−2.2 (4)	Br2A—C7A—C8A—Br1A	−176.6 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.95	2.45	3.392 (4)	170
C8—H8···O1ⁱ	1.00	2.35	3.336 (4)	169
C11—H11···O1ⁱ	0.95	2.29	3.229 (3)	170
C3—H3···Cg1ⁱⁱ	0.95	2.96	3.652 (3)	131

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

Experimental details

Crystal data
Chemical formula	C₁₅H₉Br₂Cl₂FO
M_r	454.94
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	7.1232 (1), 10.0757 (2), 43.0262 (7)
V (Å³)	3088.04 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	5.60
Crystal size (mm)	0.40 × 0.24 × 0.14

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.211, 0.508
No. of measured, independent and observed [I > 2σ(I)] reflections	26343, 5857, 3681
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.769

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.089, 0.99
No. of reflections	5857
No. of parameters	227
No. of restraints	60
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.77, −0.76

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.95	2.45	3.392 (4)	170
C8—H8···O1ⁱ	1.00	2.35	3.336 (4)	169
C11—H11···O1ⁱ	0.95	2.29	3.229 (3)	170
C3—H3···Cg1ⁱⁱ	0.95	2.96	3.652 (3)	131

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

Footnotes

‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.

Acknowledgements

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. HKF and IAR also thank the Malaysian Government and Universiti Sains Malaysia for the FRGS grant No. 203/PFIZIK/671064. SRJ thanks the Universiti Sains Malaysia for a post-doctoral research fellowship. This work was also supported by the Department of Science and Technology (DST), Government of India, grant No. SR/S2/LOP-17/2006.

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