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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807018168/sj2290sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807018168/sj2290Isup2.hkl
Contains datablock I

CCDC reference: 647586

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

Comment top

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 top

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).

Experimental top

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.

Refinement top

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

Structure description top

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.

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).

Computing details top

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 top
[Figure 1] 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.
[Figure 2] 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 top
Crystal data top
C15H11BrOZ = 2
Mr = 287.15F(000) = 288
Triclinic, P1Dx = 1.622 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.8253 (2) ÅCell parameters from 7148 reflections
b = 7.6325 (3) Åθ = 1.5–30.0°
c = 13.3374 (4) ŵ = 3.47 mm1
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) Å3
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
3398 independent reflections
Radiation source: fine-focus sealed tube3157 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 8.33 pixels mm-1θmax = 30.0°, θmin = 1.5°
ω scansh = 88
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1010
Tmin = 0.129, Tmax = 0.297l = 1818
11699 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 1.17 w = 1/[σ2(Fo2) + (0.048P)2 + 0.1299P]
where P = (Fo2 + 2Fc2)/3
3398 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.81 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
C15H11BrOγ = 87.378 (2)°
Mr = 287.15V = 588.02 (4) Å3
Triclinic, P1Z = 2
a = 5.8253 (2) ÅMo Kα radiation
b = 7.6325 (3) ŵ = 3.47 mm1
c = 13.3374 (4) ÅT = 100 K
α = 83.051 (2)°0.63 × 0.52 × 0.36 mm
β = 89.919 (2)°
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
3398 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
3157 reflections with I > 2σ(I)
Tmin = 0.129, Tmax = 0.297Rint = 0.023
11699 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0260 restraints
wR(F2) = 0.079H-atom parameters constrained
S = 1.17Δρmax = 0.81 e Å3
3398 reflectionsΔρmin = 0.35 e Å3
154 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
xyzUiso*/Ueq
Br10.18482 (3)0.30834 (2)0.437256 (12)0.02195 (7)
O10.2233 (2)0.27315 (18)0.03021 (10)0.0235 (3)
C10.4563 (3)0.0879 (2)0.17687 (13)0.0191 (3)
H1A0.50410.06850.11010.023*
C20.5930 (3)0.0399 (2)0.25316 (14)0.0204 (3)
H2A0.73140.01260.23710.024*
C30.5245 (3)0.0696 (2)0.35343 (14)0.0220 (3)
H3A0.61670.03690.40430.026*
C40.3181 (3)0.1483 (2)0.37739 (14)0.0227 (3)
H4A0.27290.16980.44450.027*
C50.1788 (3)0.1951 (2)0.30139 (13)0.0195 (3)
H5A0.03980.24620.31790.023*
C60.2459 (3)0.1658 (2)0.20008 (13)0.0170 (3)
C70.0958 (3)0.2175 (2)0.12186 (13)0.0185 (3)
H7A0.05420.24250.14040.022*
C80.1547 (3)0.2320 (2)0.02598 (13)0.0202 (3)
H8A0.30490.21280.00520.024*
C90.0163 (3)0.2781 (2)0.04731 (13)0.0185 (3)
C100.0722 (3)0.3293 (2)0.14550 (13)0.0176 (3)
C110.0729 (3)0.3005 (2)0.22996 (13)0.0173 (3)
H11A0.22040.25020.22500.021*
C120.0070 (3)0.3483 (2)0.32109 (13)0.0176 (3)
C130.2258 (3)0.4256 (2)0.33028 (14)0.0200 (3)
H13A0.27640.45680.39210.024*
C140.3671 (3)0.4554 (2)0.24598 (14)0.0206 (3)
H14A0.51280.50870.25090.025*
C150.2924 (3)0.4060 (2)0.15401 (14)0.0193 (3)
H15A0.38930.42420.09800.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02079 (10)0.02853 (11)0.01666 (10)0.00418 (7)0.00231 (6)0.00519 (6)
O10.0172 (6)0.0335 (7)0.0200 (6)0.0009 (5)0.0001 (5)0.0036 (5)
C10.0168 (7)0.0195 (7)0.0201 (8)0.0008 (6)0.0000 (6)0.0004 (6)
C20.0175 (7)0.0176 (7)0.0256 (8)0.0004 (6)0.0024 (6)0.0018 (6)
C30.0234 (8)0.0216 (7)0.0209 (8)0.0018 (6)0.0050 (6)0.0034 (6)
C40.0253 (9)0.0247 (8)0.0181 (8)0.0006 (7)0.0008 (6)0.0026 (6)
C50.0189 (7)0.0195 (7)0.0198 (8)0.0005 (6)0.0008 (6)0.0020 (6)
C60.0152 (7)0.0158 (6)0.0200 (8)0.0020 (6)0.0009 (6)0.0027 (5)
C70.0163 (7)0.0185 (7)0.0205 (8)0.0009 (6)0.0011 (6)0.0025 (6)
C80.0168 (7)0.0234 (7)0.0200 (8)0.0015 (6)0.0007 (6)0.0013 (6)
C90.0182 (7)0.0194 (7)0.0174 (7)0.0001 (6)0.0011 (6)0.0006 (6)
C100.0178 (7)0.0176 (7)0.0173 (7)0.0018 (6)0.0004 (6)0.0014 (5)
C110.0152 (7)0.0173 (7)0.0192 (8)0.0003 (6)0.0006 (6)0.0026 (5)
C120.0173 (7)0.0179 (7)0.0176 (7)0.0006 (6)0.0024 (6)0.0021 (5)
C130.0186 (8)0.0197 (7)0.0222 (8)0.0002 (6)0.0023 (6)0.0048 (6)
C140.0163 (7)0.0184 (7)0.0267 (9)0.0025 (6)0.0001 (6)0.0027 (6)
C150.0171 (7)0.0189 (7)0.0213 (8)0.0003 (6)0.0027 (6)0.0006 (6)
Geometric parameters (Å, º) top
Br1—C121.8976 (17)C7—H7A0.9300
O1—C91.226 (2)C8—C91.480 (2)
C1—C21.387 (2)C8—H8A0.9300
C1—C61.404 (2)C9—C101.496 (2)
C1—H1A0.9300C10—C151.396 (2)
C2—C31.390 (3)C10—C111.399 (2)
C2—H2A0.9300C11—C121.385 (2)
C3—C41.388 (3)C11—H11A0.9300
C3—H3A0.9300C12—C131.392 (2)
C4—C51.389 (2)C13—C141.385 (3)
C4—H4A0.9300C13—H13A0.9300
C5—C61.401 (2)C14—C151.390 (3)
C5—H5A0.9300C14—H14A0.9300
C6—C71.463 (2)C15—H15A0.9300
C7—C81.340 (2)
C2—C1—C6120.28 (16)C9—C8—H8A119.6
C2—C1—H1A119.9O1—C9—C8122.29 (16)
C6—C1—H1A119.9O1—C9—C10120.37 (15)
C1—C2—C3120.47 (16)C8—C9—C10117.33 (15)
C1—C2—H2A119.8C15—C10—C11119.95 (16)
C3—C2—H2A119.8C15—C10—C9121.73 (15)
C4—C3—C2119.77 (17)C11—C10—C9118.31 (15)
C4—C3—H3A120.1C12—C11—C10118.76 (15)
C2—C3—H3A120.1C12—C11—H11A120.6
C3—C4—C5120.17 (17)C10—C11—H11A120.6
C3—C4—H4A119.9C11—C12—C13121.74 (16)
C5—C4—H4A119.9C11—C12—Br1119.68 (13)
C4—C5—C6120.59 (16)C13—C12—Br1118.58 (13)
C4—C5—H5A119.7C14—C13—C12119.05 (16)
C6—C5—H5A119.7C14—C13—H13A120.5
C5—C6—C1118.72 (16)C12—C13—H13A120.5
C5—C6—C7119.24 (15)C13—C14—C15120.34 (16)
C1—C6—C7122.04 (15)C13—C14—H14A119.8
C8—C7—C6125.99 (16)C15—C14—H14A119.8
C8—C7—H7A117.0C14—C15—C10120.15 (16)
C6—C7—H7A117.0C14—C15—H15A119.9
C7—C8—C9120.81 (16)C10—C15—H15A119.9
C7—C8—H8A119.6
C6—C1—C2—C30.6 (3)C8—C9—C10—C1527.8 (2)
C1—C2—C3—C40.1 (3)O1—C9—C10—C1126.0 (2)
C2—C3—C4—C50.9 (3)C8—C9—C10—C11153.04 (15)
C3—C4—C5—C60.9 (3)C15—C10—C11—C120.5 (2)
C4—C5—C6—C10.2 (3)C9—C10—C11—C12179.65 (14)
C4—C5—C6—C7179.67 (16)C10—C11—C12—C130.7 (2)
C2—C1—C6—C50.5 (2)C10—C11—C12—Br1179.27 (12)
C2—C1—C6—C7179.61 (16)C11—C12—C13—C140.0 (2)
C5—C6—C7—C8165.45 (17)Br1—C12—C13—C14179.98 (12)
C1—C6—C7—C814.4 (3)C12—C13—C14—C151.1 (3)
C6—C7—C8—C9177.36 (15)C13—C14—C15—C101.3 (3)
C7—C8—C9—O113.7 (3)C11—C10—C15—C140.6 (2)
C7—C8—C9—C10167.28 (16)C9—C10—C15—C14178.60 (15)
O1—C9—C10—C15153.17 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···O10.932.522.836 (2)100
C3—H3A···Br1i0.932.973.533 (2)120
Symmetry code: (i) x1, y, z1.

Experimental details

Crystal data
Chemical formulaC15H11BrO
Mr287.15
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)5.8253 (2), 7.6325 (3), 13.3374 (4)
α, β, γ (°)83.051 (2), 89.919 (2), 87.378 (2)
V3)588.02 (4)
Z2
Radiation typeMo Kα
µ (mm1)3.47
Crystal size (mm)0.63 × 0.52 × 0.36
Data collection
DiffractometerBruker SMART APEX2 CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.129, 0.297
No. of measured, independent and
observed [I > 2σ(I)] reflections
11699, 3398, 3157
Rint0.023
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.079, 1.17
No. of reflections3398
No. of parameters154
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.81, 0.35

Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···O10.932.522.836 (2)100
C3—H3A···Br1i0.932.973.533 (2)120
Symmetry code: (i) x1, y, z1.
 

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