3-(3-Bromo­phen­yl)-1-(4-bromo­phen­yl)prop-2-en-1-one

In the title compound, C₁₅H₁₀Br₂O, the dihedral angle between the benzene rings is 48.0 (1)°. The crystal structure is stabilized by weak inter­molecular Br...Br contacts and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.047
• wR factor = 0.109
• Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.89

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.895
            Tmax scaled      0.474 Tmin scaled      0.113

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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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).

3-(3-Bromophenyl)-1-(4-bromophenyl)prop-2-en-1-one

Crystal data

C15H10Br2O	F(000) = 712
Mr = 366.05	Dx = 1.872 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6169 reflections
a = 7.1411 (2) Å	θ = 2.6–27.5°
b = 31.4292 (8) Å	µ = 6.23 mm^−1
c = 5.7876 (2) Å	T = 100 K
β = 91.275 (2)°	Block, yellow
V = 1298.64 (7) Å^3	0.40 × 0.20 × 0.12 mm
Z = 4

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	2962 independent reflections
Radiation source: fine-focus sealed tube	2448 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 8.33 pixels mm^-1	θmax = 27.5°, θmin = 2.6°
ω scans	h = −9→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −40→39
Tmin = 0.126, Tmax = 0.530	l = −7→7
14661 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H-atom parameters constrained
S = 1.20	w = 1/[σ^2(Fo^2) + (0.0308P)^2 + 4.6217P] where P = (Fo^2 + 2Fc^2)/3
2962 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 1.05 e Å^−3
0 restraints	Δρmin = −0.71 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	0.91718 (7)	−0.210296 (15)	0.86868 (8)	0.03381 (15)
Br2	0.68211 (7)	0.211369 (15)	0.61013 (8)	0.03415 (15)
O1	0.7726 (5)	−0.02389 (10)	0.2759 (5)	0.0291 (7)
C1	0.9022 (6)	−0.07989 (15)	0.7967 (7)	0.0257 (9)
H1A	0.9311	−0.0565	0.8892	0.031*
C2	0.9380 (6)	−0.12056 (15)	0.8782 (7)	0.0265 (9)
H2A	0.9971	−0.1246	1.0213	0.032*
C3	0.8849 (6)	−0.15502 (14)	0.7444 (7)	0.0244 (9)
C4	0.8085 (6)	−0.15005 (15)	0.5223 (8)	0.0277 (9)
H4A	0.7789	−0.1736	0.4314	0.033*
C5	0.7777 (6)	−0.10916 (15)	0.4399 (7)	0.0249 (9)
H5A	0.7264	−0.1052	0.2924	0.030*
C6	0.8232 (6)	−0.07378 (14)	0.5774 (7)	0.0235 (9)
C7	0.7800 (6)	−0.03038 (14)	0.4843 (7)	0.0247 (9)
C8	0.7435 (6)	0.00407 (15)	0.6535 (7)	0.0261 (9)
H8A	0.7297	−0.0026	0.8086	0.031*
C9	0.7305 (6)	0.04422 (15)	0.5856 (7)	0.0245 (9)
H9A	0.7533	0.0494	0.4305	0.029*
C10	0.6844 (6)	0.08145 (14)	0.7246 (7)	0.0230 (9)
C11	0.7100 (6)	0.12177 (14)	0.6313 (7)	0.0240 (9)
H11A	0.7641	0.1247	0.4874	0.029*
C12	0.6555 (6)	0.15750 (14)	0.7512 (7)	0.0236 (9)
C13	0.5788 (6)	0.15431 (15)	0.9688 (8)	0.0270 (9)
H13A	0.5443	0.1786	1.0496	0.032*
C14	0.5548 (7)	0.11412 (15)	1.0632 (8)	0.0288 (10)
H14A	0.5027	0.1115	1.2084	0.035*
C15	0.6072 (6)	0.07779 (15)	0.9443 (7)	0.0257 (9)
H15A	0.5911	0.0511	1.0103	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0377 (3)	0.0258 (3)	0.0379 (3)	0.0045 (2)	0.0003 (2)	0.00326 (19)
Br2	0.0443 (3)	0.0220 (2)	0.0362 (3)	−0.0028 (2)	0.0026 (2)	0.00169 (19)
O1	0.0351 (18)	0.0299 (18)	0.0224 (15)	0.0006 (14)	−0.0005 (13)	0.0002 (13)
C1	0.029 (2)	0.025 (2)	0.023 (2)	0.0007 (18)	0.0013 (17)	−0.0030 (17)
C2	0.021 (2)	0.035 (3)	0.023 (2)	0.0013 (18)	0.0034 (17)	−0.0017 (18)
C3	0.027 (2)	0.022 (2)	0.024 (2)	0.0036 (17)	0.0030 (17)	0.0016 (16)
C4	0.028 (2)	0.025 (2)	0.030 (2)	0.0006 (18)	0.0045 (18)	−0.0046 (18)
C5	0.020 (2)	0.035 (3)	0.020 (2)	0.0020 (18)	−0.0008 (16)	−0.0020 (17)
C6	0.022 (2)	0.027 (2)	0.022 (2)	−0.0021 (17)	0.0044 (16)	−0.0021 (16)
C7	0.023 (2)	0.026 (2)	0.025 (2)	−0.0016 (17)	0.0022 (17)	−0.0024 (17)
C8	0.027 (2)	0.028 (2)	0.023 (2)	−0.0004 (18)	0.0022 (17)	−0.0016 (17)
C9	0.022 (2)	0.030 (2)	0.022 (2)	−0.0030 (18)	−0.0017 (16)	0.0006 (17)
C10	0.024 (2)	0.023 (2)	0.022 (2)	−0.0008 (17)	0.0009 (16)	0.0003 (16)
C11	0.024 (2)	0.025 (2)	0.023 (2)	−0.0024 (17)	−0.0003 (16)	−0.0004 (16)
C12	0.026 (2)	0.019 (2)	0.026 (2)	−0.0022 (17)	−0.0028 (17)	0.0005 (16)
C13	0.030 (2)	0.026 (2)	0.025 (2)	0.0003 (18)	−0.0010 (18)	−0.0030 (17)
C14	0.027 (2)	0.036 (3)	0.024 (2)	0.0015 (19)	0.0023 (17)	−0.0003 (18)
C15	0.030 (2)	0.026 (2)	0.021 (2)	−0.0022 (18)	−0.0036 (17)	0.0012 (16)

Geometric parameters (Å, º)

Br1—C3	1.892 (4)	C8—C9	1.324 (6)
Br2—C12	1.891 (4)	C8—H8A	0.9300
O1—C7	1.223 (5)	C9—C10	1.462 (6)
C1—C2	1.385 (7)	C9—H9A	0.9300
C1—C6	1.391 (6)	C10—C11	1.392 (6)
C1—H1A	0.9300	C10—C15	1.402 (6)
C2—C3	1.380 (6)	C11—C12	1.380 (6)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.394 (6)	C12—C13	1.388 (6)
C4—C5	1.386 (6)	C13—C14	1.388 (7)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.402 (6)	C14—C15	1.389 (6)
C5—H5A	0.9300	C14—H14A	0.9300
C6—C7	1.496 (6)	C15—H15A	0.9300
C7—C8	1.487 (6)
C2—C1—C6	120.4 (4)	C7—C8—H8A	119.6
C2—C1—H1A	119.8	C8—C9—C10	127.9 (4)
C6—C1—H1A	119.8	C8—C9—H9A	116.0
C3—C2—C1	119.2 (4)	C10—C9—H9A	116.0
C3—C2—H2A	120.4	C11—C10—C15	119.0 (4)
C1—C2—H2A	120.4	C11—C10—C9	118.8 (4)
C2—C3—C4	121.8 (4)	C15—C10—C9	122.1 (4)
C2—C3—Br1	118.5 (3)	C12—C11—C10	120.3 (4)
C4—C3—Br1	119.7 (3)	C12—C11—H11A	119.8
C5—C4—C3	118.5 (4)	C10—C11—H11A	119.8
C5—C4—H4A	120.8	C11—C12—C13	121.3 (4)
C3—C4—H4A	120.8	C11—C12—Br2	118.6 (3)
C4—C5—C6	120.5 (4)	C13—C12—Br2	120.1 (3)
C4—C5—H5A	119.8	C14—C13—C12	118.5 (4)
C6—C5—H5A	119.8	C14—C13—H13A	120.7
C1—C6—C5	119.5 (4)	C12—C13—H13A	120.7
C1—C6—C7	122.1 (4)	C13—C14—C15	121.1 (4)
C5—C6—C7	118.4 (4)	C13—C14—H14A	119.5
O1—C7—C8	121.6 (4)	C15—C14—H14A	119.5
O1—C7—C6	120.8 (4)	C14—C15—C10	119.8 (4)
C8—C7—C6	117.7 (4)	C14—C15—H15A	120.1
C9—C8—C7	120.7 (4)	C10—C15—H15A	120.1
C9—C8—H8A	119.6
C6—C1—C2—C3	−3.5 (6)	C6—C7—C8—C9	170.5 (4)
C1—C2—C3—C4	4.7 (7)	C7—C8—C9—C10	176.0 (4)
C1—C2—C3—Br1	−175.1 (3)	C8—C9—C10—C11	168.7 (5)
C2—C3—C4—C5	−3.1 (7)	C8—C9—C10—C15	−14.3 (7)
Br1—C3—C4—C5	176.8 (3)	C15—C10—C11—C12	−1.6 (6)
C3—C4—C5—C6	0.2 (6)	C9—C10—C11—C12	175.4 (4)
C2—C1—C6—C5	0.8 (6)	C10—C11—C12—C13	1.6 (7)
C2—C1—C6—C7	179.2 (4)	C10—C11—C12—Br2	−176.9 (3)
C4—C5—C6—C1	0.9 (6)	C11—C12—C13—C14	−1.0 (7)
C4—C5—C6—C7	−177.6 (4)	Br2—C12—C13—C14	177.5 (3)
C1—C6—C7—O1	154.9 (4)	C12—C13—C14—C15	0.5 (7)
C5—C6—C7—O1	−26.7 (6)	C13—C14—C15—C10	−0.5 (7)
C1—C6—C7—C8	−26.2 (6)	C11—C10—C15—C14	1.1 (7)
C5—C6—C7—C8	152.2 (4)	C9—C10—C15—C14	−175.8 (4)
O1—C7—C8—C9	−10.6 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1	0.93	2.48	2.812 (5)	101
C2—H2A···Cg2^i	0.93	2.75	3.428 (5)	131
C5—H5A···Cg2^ii	0.93	2.69	3.342 (5)	127
C11—H11A···Cg1^iii	0.93	2.88	3.568 (5)	132
C14—H14A···Cg1^iv	0.93	2.69	3.373 (5)	131

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