3-(3-Bromo­phen­yl)-1-phenyl­prop-2-en-1-one

The enone group and the benzene rings of the title compound, C₁₅H₁₁BrO, are each planar. The mol­ecules are linked via C—H...O inter­actions into wave-like chains along the c axis and the chains are stacked along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.030
• wR factor = 0.090
• Data-to-parameter ratio = 47.7

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.065     0.357
            Tmin(prime) and Tmax expected:      0.073     0.357
            RR(prime) =      0.894
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.82
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.75 mm

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

---

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-phenylprop-2-en-1-one

Crystal data

C15H11BrO	F(000) = 576
Mr = 287.15	Dx = 1.602 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6943 reflections
a = 14.3238 (2) Å	θ = 1.5–40.0°
b = 7.4913 (1) Å	µ = 3.43 mm^−1
c = 11.2786 (2) Å	T = 100 K
β = 100.325 (1)°	Block, colourless
V = 1190.64 (3) Å^3	0.75 × 0.33 × 0.30 mm
Z = 4

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	7339 independent reflections
Radiation source: fine-focus sealed tube	5499 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 8.33 pixels mm^-1	θmax = 40.0°, θmin = 1.5°
ω scans	h = −25→25
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
Tmin = 0.065, Tmax = 0.357	l = −20→20
48289 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0447P)^2 + 0.2439P] where P = (Fo^2 + 2Fc^2)/3
7339 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.71 e Å^−3
0 restraints	Δρmin = −0.74 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	0.051212 (8)	0.146151 (18)	0.354188 (11)	0.02510 (4)
O1	0.56241 (7)	0.35956 (15)	0.28726 (9)	0.0300 (2)
C1	0.25135 (7)	0.18417 (14)	0.39756 (9)	0.01602 (16)
H1	0.2418	0.2255	0.3186	0.019*
C2	0.17477 (7)	0.13070 (14)	0.44858 (10)	0.01682 (16)
C3	0.18626 (8)	0.06554 (15)	0.56568 (10)	0.01849 (17)
H3	0.1342	0.0302	0.5988	0.022*
C4	0.27793 (8)	0.05477 (15)	0.63198 (9)	0.01779 (17)
H4	0.2872	0.0096	0.7100	0.021*
C5	0.35594 (8)	0.11021 (14)	0.58376 (9)	0.01608 (16)
H5	0.4165	0.1038	0.6300	0.019*
C6	0.34334 (7)	0.17568 (14)	0.46554 (9)	0.01489 (15)
C7	0.42251 (7)	0.23457 (15)	0.40964 (9)	0.01744 (16)
H7	0.4106	0.2460	0.3262	0.021*
C8	0.51034 (7)	0.27372 (15)	0.46630 (9)	0.01728 (16)
H8	0.5258	0.2640	0.5497	0.021*
C9	0.58306 (8)	0.33260 (15)	0.39628 (10)	0.01763 (17)
C10	0.68334 (7)	0.35655 (13)	0.45847 (9)	0.01487 (15)
C11	0.71657 (7)	0.29987 (15)	0.57681 (9)	0.01653 (16)
H11	0.6745	0.2529	0.6226	0.020*
C12	0.81274 (8)	0.31397 (16)	0.62580 (10)	0.01935 (18)
H12	0.8348	0.2757	0.7043	0.023*
C13	0.87602 (8)	0.38499 (17)	0.55797 (11)	0.02131 (19)
H13	0.9403	0.3927	0.5907	0.026*
C14	0.84298 (8)	0.44442 (16)	0.44108 (11)	0.02104 (19)
H14	0.8850	0.4935	0.3961	0.025*
C15	0.74754 (7)	0.43038 (15)	0.39188 (9)	0.01794 (17)
H15	0.7258	0.4704	0.3138	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.01137 (5)	0.03721 (8)	0.02575 (6)	−0.00286 (4)	0.00069 (4)	0.00032 (4)
O1	0.0176 (4)	0.0540 (7)	0.0174 (3)	−0.0070 (4)	0.0004 (3)	0.0095 (4)
C1	0.0128 (4)	0.0201 (4)	0.0152 (4)	−0.0015 (3)	0.0026 (3)	0.0001 (3)
C2	0.0119 (4)	0.0205 (4)	0.0182 (4)	−0.0017 (3)	0.0030 (3)	−0.0015 (3)
C3	0.0161 (4)	0.0214 (5)	0.0193 (4)	−0.0028 (3)	0.0067 (3)	−0.0011 (3)
C4	0.0185 (4)	0.0199 (4)	0.0158 (4)	−0.0011 (3)	0.0052 (3)	0.0004 (3)
C5	0.0148 (4)	0.0183 (4)	0.0150 (4)	−0.0005 (3)	0.0025 (3)	−0.0003 (3)
C6	0.0122 (3)	0.0178 (4)	0.0149 (4)	−0.0013 (3)	0.0027 (3)	−0.0001 (3)
C7	0.0134 (4)	0.0230 (5)	0.0161 (4)	−0.0015 (3)	0.0033 (3)	0.0019 (3)
C8	0.0133 (4)	0.0230 (5)	0.0159 (4)	−0.0019 (3)	0.0035 (3)	−0.0001 (3)
C9	0.0129 (4)	0.0231 (5)	0.0170 (4)	−0.0013 (3)	0.0028 (3)	0.0017 (3)
C10	0.0124 (3)	0.0173 (4)	0.0151 (3)	−0.0009 (3)	0.0031 (3)	−0.0010 (3)
C11	0.0142 (4)	0.0199 (4)	0.0157 (4)	−0.0009 (3)	0.0035 (3)	−0.0006 (3)
C12	0.0155 (4)	0.0245 (5)	0.0177 (4)	−0.0004 (3)	0.0019 (3)	−0.0010 (3)
C13	0.0131 (4)	0.0276 (5)	0.0228 (4)	−0.0033 (3)	0.0021 (3)	−0.0025 (4)
C14	0.0154 (4)	0.0259 (5)	0.0228 (4)	−0.0052 (3)	0.0061 (3)	−0.0014 (4)
C15	0.0158 (4)	0.0213 (5)	0.0173 (4)	−0.0031 (3)	0.0046 (3)	0.0002 (3)

Geometric parameters (Å, º)

Br1—C2	1.8983 (11)	C8—C9	1.4826 (14)
O1—C9	1.2287 (14)	C8—H8	0.93
C1—C2	1.3861 (14)	C9—C10	1.4920 (15)
C1—C6	1.4021 (14)	C10—C11	1.4002 (14)
C1—H1	0.93	C10—C15	1.4011 (14)
C2—C3	1.3898 (15)	C11—C12	1.3932 (15)
C3—C4	1.3921 (16)	C11—H11	0.93
C3—H3	0.93	C12—C13	1.3923 (16)
C4—C5	1.3910 (15)	C12—H12	0.93
C4—H4	0.93	C13—C14	1.3916 (17)
C5—C6	1.4017 (14)	C13—H13	0.93
C5—H5	0.93	C14—C15	1.3841 (15)
C6—C7	1.4609 (14)	C14—H14	0.93
C7—C8	1.3376 (15)	C15—H15	0.93
C7—H7	0.93
C2—C1—C6	119.73 (9)	C9—C8—H8	120.0
C2—C1—H1	120.1	O1—C9—C8	121.06 (10)
C6—C1—H1	120.1	O1—C9—C10	119.31 (9)
C1—C2—C3	121.89 (10)	C8—C9—C10	119.63 (9)
C1—C2—Br1	118.50 (8)	C11—C10—C15	119.14 (9)
C3—C2—Br1	119.61 (8)	C11—C10—C9	123.08 (9)
C2—C3—C4	118.06 (9)	C15—C10—C9	117.68 (9)
C2—C3—H3	121.0	C12—C11—C10	119.87 (9)
C4—C3—H3	121.0	C12—C11—H11	120.1
C5—C4—C3	121.28 (10)	C10—C11—H11	120.1
C5—C4—H4	119.4	C13—C12—C11	120.39 (10)
C3—C4—H4	119.4	C13—C12—H12	119.8
C4—C5—C6	120.06 (10)	C11—C12—H12	119.8
C4—C5—H5	120.0	C14—C13—C12	119.89 (10)
C6—C5—H5	120.0	C14—C13—H13	120.1
C5—C6—C1	118.97 (9)	C12—C13—H13	120.1
C5—C6—C7	122.58 (9)	C15—C14—C13	119.95 (10)
C1—C6—C7	118.45 (9)	C15—C14—H14	120.0
C8—C7—C6	126.62 (9)	C13—C14—H14	120.0
C8—C7—H7	116.7	C14—C15—C10	120.73 (10)
C6—C7—H7	116.7	C14—C15—H15	119.6
C7—C8—C9	120.08 (9)	C10—C15—H15	119.6
C7—C8—H8	120.0
C6—C1—C2—C3	−1.03 (16)	C7—C8—C9—C10	−173.28 (10)
C6—C1—C2—Br1	179.44 (8)	O1—C9—C10—C11	−168.62 (11)
C1—C2—C3—C4	−0.01 (16)	C8—C9—C10—C11	10.31 (16)
Br1—C2—C3—C4	179.51 (8)	O1—C9—C10—C15	7.73 (16)
C2—C3—C4—C5	1.08 (16)	C8—C9—C10—C15	−173.34 (10)
C3—C4—C5—C6	−1.10 (16)	C15—C10—C11—C12	−1.33 (16)
C4—C5—C6—C1	0.04 (16)	C9—C10—C11—C12	174.96 (10)
C4—C5—C6—C7	−179.52 (10)	C10—C11—C12—C13	0.33 (17)
C2—C1—C6—C5	1.00 (15)	C11—C12—C13—C14	0.82 (18)
C2—C1—C6—C7	−179.43 (10)	C12—C13—C14—C15	−0.96 (18)
C5—C6—C7—C8	−16.42 (18)	C13—C14—C15—C10	−0.06 (18)
C1—C6—C7—C8	164.02 (11)	C11—C10—C15—C14	1.21 (16)
C6—C7—C8—C9	−179.79 (10)	C9—C10—C15—C14	−175.29 (10)
C7—C8—C9—O1	5.64 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.93	2.45	2.7909 (15)	102
C5—H5···O1^i	0.93	2.50	3.4106 (15)	166

Symmetry code: (i) x, −y+1/2, z+1/2.