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

In the title compound, C₁₅H₁₁BrO, the dihedral angle between the two benzene rings is 49.93 (8)°. The mol­ecules are arranged into infinite chains along the c axis through weak C—H...Br inter­actions. The chains are stacked along the a axis, forming layers.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.026
• wR factor = 0.079
• Data-to-parameter ratio = 22.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.63 mm
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.31
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         200 Deg.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3A    ..  BR1     ..       2.97 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Among several organic compounds reported for their NLO properties, chalcone derivatives are prominent materials for their excellent blue light transmittance and good crystallizability (Patil, Teh et al., 2006; Patil, Dharmaprakash et al., 2006; Shettigar et al., 2006; Patil, Ng et al., 2007; Patil, Rosli et al., 2007). The title compound, (I), was prepared as part of our ongoing studies on nonlinear optical (NLO) materials (Patil et al., 2007). Crystal of the title compound, (I) (Fig. 1), do not exhibit second-order nonlinear optical properties as they crystallize in a centrosymmeric space group.

In (I), bond lengths and angles have normal values (Allen et al., 1987) and comparable to those in related structures (Patil, Teh et al., 2006; Patil, Dharmaprakash et al., 2006; Shettigar et al., 2006; Patil, Ng et al., 2007). The least-squares plane through the O1/C7/C8/C9 enone group makes dihedral angles of 24.04 (7)° and 27.55 (7)° with the C1—C6 and C10—C15 benzene rings, respectively. The dihedral angle between the two benzene rings is 49.93 (8)°.

In the crystal structure of (I), the intramolecular C7—H7A···O1 interaction generates an S(5) ring motif (Bernstein et al., 1995). The molecules are arranged into infinite chains along the c axis through weak C3—H3A···Br1ⁱ interactions. These chain are stacked along the a axis to form layers.

Related literature

For related literature on hydrogen-bond motifs, see Bernstein et al. (1995). For related literature on values of bond lengths and angles, see Allen et al. (1987). For related structures see, for example, Patil, Dharmaprakash, Fun et al., (2006); Patil, Dharmaprakash, Ramakrishna et al., (2007); Patil, Ng, et al., (2007); Patil, Rosli et al., (2007); Patil, Teh et al., (2006); Shettigar et al. (2006).

S2. Experimental

Benzaldehyde (0.01 mol) and 3-bromoacetophenone (0.01 mol)were stirred in 60 ml of methanol at room temperature. 5 ml of 10% of NaOH aqueous solution was added and the mixture was stirred for 2 h. The precipitate was filtered, washed with water, dried and the crude product recrystallized from acetone. Crystal suitable for X-ray analysis were grown by slow evaporation of an acetone solution at room temperature.

S3. Refinement

All H atoms were refined using a riding model, with C—H=0.9Å and U_iso(H)=1.2U_eq(C).

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).

Figures

	Fig. 1. The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atomic numbering. The intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines.

(2E)-1-(3-bromophenyl)-3-phenylprop-2-en-1-one

Crystal data

C15H11BrO	Z = 2
Mr = 287.15	F(000) = 288
Triclinic, P1	Dx = 1.622 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8253 (2) Å	Cell parameters from 7148 reflections
b = 7.6325 (3) Å	θ = 1.5–30.0°
c = 13.3374 (4) Å	µ = 3.47 mm^−1
α = 83.051 (2)°	T = 100 K
β = 89.919 (2)°	Block, colourless
γ = 87.378 (2)°	0.63 × 0.52 × 0.36 mm
V = 588.02 (4) Å^3

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	3398 independent reflections
Radiation source: fine-focus sealed tube	3157 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.33 pixels mm^-1	θmax = 30.0°, θmin = 1.5°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
Tmin = 0.129, Tmax = 0.297	l = −18→18
11699 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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.079	H-atom parameters constrained
S = 1.17	w = 1/[σ^2(Fo^2) + (0.048P)^2 + 0.1299P] where P = (Fo^2 + 2Fc^2)/3
3398 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.81 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.18482 (3)	0.30834 (2)	0.437256 (12)	0.02195 (7)
O1	0.2233 (2)	0.27315 (18)	0.03021 (10)	0.0235 (3)
C1	−0.4563 (3)	0.0879 (2)	−0.17687 (13)	0.0191 (3)
H1A	−0.5041	0.0685	−0.1101	0.023*
C2	−0.5930 (3)	0.0399 (2)	−0.25316 (14)	0.0204 (3)
H2A	−0.7314	−0.0126	−0.2371	0.024*
C3	−0.5245 (3)	0.0696 (2)	−0.35343 (14)	0.0220 (3)
H3A	−0.6167	0.0369	−0.4043	0.026*
C4	−0.3181 (3)	0.1483 (2)	−0.37739 (14)	0.0227 (3)
H4A	−0.2729	0.1698	−0.4445	0.027*
C5	−0.1788 (3)	0.1951 (2)	−0.30139 (13)	0.0195 (3)
H5A	−0.0398	0.2462	−0.3179	0.023*
C6	−0.2459 (3)	0.1658 (2)	−0.20008 (13)	0.0170 (3)
C7	−0.0958 (3)	0.2175 (2)	−0.12186 (13)	0.0185 (3)
H7A	0.0542	0.2425	−0.1404	0.022*
C8	−0.1547 (3)	0.2320 (2)	−0.02598 (13)	0.0202 (3)
H8A	−0.3049	0.2128	−0.0052	0.024*
C9	0.0163 (3)	0.2781 (2)	0.04731 (13)	0.0185 (3)
C10	−0.0722 (3)	0.3293 (2)	0.14550 (13)	0.0176 (3)
C11	0.0729 (3)	0.3005 (2)	0.22996 (13)	0.0173 (3)
H11A	0.2204	0.2502	0.2250	0.021*
C12	−0.0070 (3)	0.3483 (2)	0.32109 (13)	0.0176 (3)
C13	−0.2258 (3)	0.4256 (2)	0.33028 (14)	0.0200 (3)
H13A	−0.2764	0.4568	0.3921	0.024*
C14	−0.3671 (3)	0.4554 (2)	0.24598 (14)	0.0206 (3)
H14A	−0.5128	0.5087	0.2509	0.025*
C15	−0.2924 (3)	0.4060 (2)	0.15401 (14)	0.0193 (3)
H15A	−0.3893	0.4242	0.0980	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02079 (10)	0.02853 (11)	0.01666 (10)	0.00418 (7)	−0.00231 (6)	−0.00519 (6)
O1	0.0172 (6)	0.0335 (7)	0.0200 (6)	−0.0009 (5)	0.0001 (5)	−0.0036 (5)
C1	0.0168 (7)	0.0195 (7)	0.0201 (8)	0.0008 (6)	0.0000 (6)	−0.0004 (6)
C2	0.0175 (7)	0.0176 (7)	0.0256 (8)	0.0004 (6)	−0.0024 (6)	−0.0018 (6)
C3	0.0234 (8)	0.0216 (7)	0.0209 (8)	0.0018 (6)	−0.0050 (6)	−0.0034 (6)
C4	0.0253 (9)	0.0247 (8)	0.0181 (8)	0.0006 (7)	−0.0008 (6)	−0.0026 (6)
C5	0.0189 (7)	0.0195 (7)	0.0198 (8)	0.0005 (6)	0.0008 (6)	−0.0020 (6)
C6	0.0152 (7)	0.0158 (6)	0.0200 (8)	0.0020 (6)	−0.0009 (6)	−0.0027 (5)
C7	0.0163 (7)	0.0185 (7)	0.0205 (8)	0.0009 (6)	−0.0011 (6)	−0.0025 (6)
C8	0.0168 (7)	0.0234 (7)	0.0200 (8)	−0.0015 (6)	−0.0007 (6)	−0.0013 (6)
C9	0.0182 (7)	0.0194 (7)	0.0174 (7)	−0.0001 (6)	−0.0011 (6)	−0.0006 (6)
C10	0.0178 (7)	0.0176 (7)	0.0173 (7)	−0.0018 (6)	−0.0004 (6)	−0.0014 (5)
C11	0.0152 (7)	0.0173 (7)	0.0192 (8)	0.0003 (6)	−0.0006 (6)	−0.0026 (5)
C12	0.0173 (7)	0.0179 (7)	0.0176 (7)	0.0006 (6)	−0.0024 (6)	−0.0021 (5)
C13	0.0186 (8)	0.0197 (7)	0.0222 (8)	−0.0002 (6)	0.0023 (6)	−0.0048 (6)
C14	0.0163 (7)	0.0184 (7)	0.0267 (9)	0.0025 (6)	−0.0001 (6)	−0.0027 (6)
C15	0.0171 (7)	0.0189 (7)	0.0213 (8)	0.0003 (6)	−0.0027 (6)	−0.0006 (6)

Geometric parameters (Å, º)

Br1—C12	1.8976 (17)	C7—H7A	0.9300
O1—C9	1.226 (2)	C8—C9	1.480 (2)
C1—C2	1.387 (2)	C8—H8A	0.9300
C1—C6	1.404 (2)	C9—C10	1.496 (2)
C1—H1A	0.9300	C10—C15	1.396 (2)
C2—C3	1.390 (3)	C10—C11	1.399 (2)
C2—H2A	0.9300	C11—C12	1.385 (2)
C3—C4	1.388 (3)	C11—H11A	0.9300
C3—H3A	0.9300	C12—C13	1.392 (2)
C4—C5	1.389 (2)	C13—C14	1.385 (3)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.401 (2)	C14—C15	1.390 (3)
C5—H5A	0.9300	C14—H14A	0.9300
C6—C7	1.463 (2)	C15—H15A	0.9300
C7—C8	1.340 (2)
C2—C1—C6	120.28 (16)	C9—C8—H8A	119.6
C2—C1—H1A	119.9	O1—C9—C8	122.29 (16)
C6—C1—H1A	119.9	O1—C9—C10	120.37 (15)
C1—C2—C3	120.47 (16)	C8—C9—C10	117.33 (15)
C1—C2—H2A	119.8	C15—C10—C11	119.95 (16)
C3—C2—H2A	119.8	C15—C10—C9	121.73 (15)
C4—C3—C2	119.77 (17)	C11—C10—C9	118.31 (15)
C4—C3—H3A	120.1	C12—C11—C10	118.76 (15)
C2—C3—H3A	120.1	C12—C11—H11A	120.6
C3—C4—C5	120.17 (17)	C10—C11—H11A	120.6
C3—C4—H4A	119.9	C11—C12—C13	121.74 (16)
C5—C4—H4A	119.9	C11—C12—Br1	119.68 (13)
C4—C5—C6	120.59 (16)	C13—C12—Br1	118.58 (13)
C4—C5—H5A	119.7	C14—C13—C12	119.05 (16)
C6—C5—H5A	119.7	C14—C13—H13A	120.5
C5—C6—C1	118.72 (16)	C12—C13—H13A	120.5
C5—C6—C7	119.24 (15)	C13—C14—C15	120.34 (16)
C1—C6—C7	122.04 (15)	C13—C14—H14A	119.8
C8—C7—C6	125.99 (16)	C15—C14—H14A	119.8
C8—C7—H7A	117.0	C14—C15—C10	120.15 (16)
C6—C7—H7A	117.0	C14—C15—H15A	119.9
C7—C8—C9	120.81 (16)	C10—C15—H15A	119.9
C7—C8—H8A	119.6
C6—C1—C2—C3	−0.6 (3)	C8—C9—C10—C15	−27.8 (2)
C1—C2—C3—C4	−0.1 (3)	O1—C9—C10—C11	−26.0 (2)
C2—C3—C4—C5	0.9 (3)	C8—C9—C10—C11	153.04 (15)
C3—C4—C5—C6	−0.9 (3)	C15—C10—C11—C12	0.5 (2)
C4—C5—C6—C1	0.2 (3)	C9—C10—C11—C12	179.65 (14)
C4—C5—C6—C7	−179.67 (16)	C10—C11—C12—C13	−0.7 (2)
C2—C1—C6—C5	0.5 (2)	C10—C11—C12—Br1	179.27 (12)
C2—C1—C6—C7	−179.61 (16)	C11—C12—C13—C14	0.0 (2)
C5—C6—C7—C8	165.45 (17)	Br1—C12—C13—C14	179.98 (12)
C1—C6—C7—C8	−14.4 (3)	C12—C13—C14—C15	1.1 (3)
C6—C7—C8—C9	177.36 (15)	C13—C14—C15—C10	−1.3 (3)
C7—C8—C9—O1	−13.7 (3)	C11—C10—C15—C14	0.6 (2)
C7—C8—C9—C10	167.28 (16)	C9—C10—C15—C14	−178.60 (15)
O1—C9—C10—C15	153.17 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O1	0.93	2.52	2.836 (2)	100
C3—H3A···Br1^i	0.93	2.97	3.533 (2)	120

Symmetry code: (i) x−1, y, z−1.