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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 2| February 2009| Pages o420-o421

(E)-3-(Anthracen-9-yl)-1-(4-bromo­phen­yl)prop-2-en-1-one

aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, cDepartment of Physics, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: suchada.c@psu.ac.th

(Received 31 December 2008; accepted 26 January 2009; online 31 January 2009)

In the title mol­ecule, C23H15BrO, the prop-2-en-1-one unit is planar and it makes dihedral angles of 20.9 (1) and 45.8 (1)°, respectively, with the 4-bromo­phenyl ring and the anthracene ring system. The interplanar angle between the 4-bromophenyl ring and the anthracene ring system is 35.52 (7)°. In the crystal structure, mol­ecules are linked into dimers by C—H⋯Br hydrogen bonds, and the dimers are linked into a zigzag network parallel to the bc plane by weak C—H⋯O hydrogen bonds and C—H⋯π inter­actions involving the central benzene ring of the anthracene ring system.

Related literature

For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For related structures, see: Ng et al. (2006[Ng, S.-L., Shettigar, V., Razak, I. A., Fun, H.-K., Patil, P. S. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o1570-o1572.]); Patil et al. (2006[Patil, P. S., Rosli, M. M., Fun, H.-K., Razak, I. A., Puranik, V. G. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o4798-o4799.]); Patil, Chantrapromma et al. (2007[Patil, P. S., Chantrapromma, S., Fun, H.-K., Dharmaprakash, S. M. & Babu, H. B. R. (2007). Acta Cryst. E63, o2612.]); Suwunwong et al. (2009[Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2009). Acta Cryst. E65, o120.]). For background and applications of chalcones, see: Jung et al. (2008[Jung, Y. J., Son, K. I., Oh, Y. E. & Noh, D. Y. (2008). Polyhedron, 27, 861-867.]); Patil, Chantrapromma et al. (2007[Patil, P. S., Chantrapromma, S., Fun, H.-K., Dharmaprakash, S. M. & Babu, H. B. R. (2007). Acta Cryst. E63, o2612.]); Patil, Dharmaprakash et al. (2007[Patil, P. S., Dharmaprakash, S. M., Ramakrishna, K., Fun, H. K., Sai Santosh Kumar, R. & Narayana Rao, D. (2007). J. Cryst. Growth, 303, 520-524.]); Patil & Dharmaprakash (2008[Patil, P. S. & Dharmaprakash, S. M. (2008). Mater. Lett. 62, 451-453.]); Prasad et al. (2008[Prasad, Y. R., Kumar, P. R., Smile, D. J. & Babu, P. A. (2008). Arkivoc, 11, 266-276.]).

[Scheme 1]

Experimental

Crystal data
  • C23H15BrO

  • Mr = 387.25

  • Monoclinic, P 21 /c

  • a = 5.3792 (1) Å

  • b = 19.1030 (4) Å

  • c = 16.3005 (4) Å

  • β = 95.944 (1)°

  • V = 1666.02 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.47 mm−1

  • T = 100.0 (1) K

  • 0.57 × 0.27 × 0.15 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.331, Tmax = 0.714

  • 29994 measured reflections

  • 4866 independent reflections

  • 3803 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.076

  • S = 1.02

  • 4866 reflections

  • 226 parameters

  • H-atom parameters constrained

  • Δρmax = 0.53 e Å−3

  • Δρmin = −0.54 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C18–C23 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8A⋯O1i 0.93 2.42 3.308 (2) 159
C13—H13A⋯O1ii 0.93 2.57 3.288 (2) 135
C21—H21A⋯Br1iii 0.93 2.93 3.4722 (19) 119
C9—H9ACg1iv 0.93 2.83 3.4479 (18) 125
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y+1, -z+2; (iii) -x, -y+1, -z+1; (iv) x+1, y, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information


Comment top

Chalcones are compounds which have a wide range of applications covering from non-linear optical (Patil & Dharmaprakash, 2008) and electro-active fluorescent materials (Jung et al., 2008) to materials with various biological activities (Prasad et al., 2008). Our previous work (Patil Dharmaprakash et al., 2007) has reported that 1-(4-bromophenyl)-3-(2,4,5-trimethoxyphenyl)-propenone shows efficient second-order nonlinear optical properties. The various interesting properties of chalcone derivatives lead us to synthesize the title chalcone derivative in order to study its photoluminescence and antimicrobial activities.

The molecule of the title chalcone derivative (Fig. 1) exists in an E configuration with respect to the C8C9 double bond [1.333 (2) Å]. The anthracene ring system is planar, with atom C21 deviating a maximum of 0.147 (2) Å. The molecule is twisted as indicated by the interplanar angle between 4-bromophenyl ring and anthracene ring system of 35.52 (7)°, and torsion angles C5–C6–C7–C8 of 22.9 (1)° and C8–C9–C10–C23 of -50.2 (3)°. The pro-2-en-1-one unit (C7-C9/O1) is planar as evidenced by the torsion angle O1–C7–C8–C9 of 0.1 (3)°. The O1/C6-C9 plane makes dihedral angles of 20.9 (1)° and 45.8 (1)°, respectively, with the 4-bromophenyl ring and anthracene ring system. The bond distances show normal values (Allen et al., 1987) and are comparable with those observed in related structures (Ng et al., 2006; Patil et al., 2006; Patil, Chantrapromma et al., 2007; Suwunwong et al., 2009).

In the crystal packing (Fig. 2), the molecules are linked into dimers by weak C—H···Br interactions (Table 1) and the dimers are further linked into a zigzag network parallel to the bc plane by weak C—H···O and C—H···π interactions (Table 1).

Related literature top

For bond-length data, see: Allen et al. (1987). For related structures, see: Ng et al. (2006); Patil et al. (2006); Patil, Chantrapromma et al. (2007); Suwunwong et al. (2009). For background and applications of chalcones, see: Jung et al. (2008); Patil, Chantrapromma et al. (2007); Patil, Dharmaprakash et al. (2007); Patil & Dharmaprakash (2008); Prasad et al. (2008).

Experimental top

The title compound was synthesized by the condensation of anthracene-9-carbaldehyde (0.01 mol) with 4-bromoacetophenone (0.01 mol) in ethanol (40 ml) in the presence of NaOH (10 ml, 10%). After stirring for 2 h, a yellow solid appeared and was then collected by filtration, washed with distilled water, dried and purified by repeated recrystallization from acetone. Yellow plate-shaped single crystals of the title compound suitable for X-ray structure determination were obtained by slow evaporation of an acetone solution at room temperature after several days.

Refinement top

All H atoms were placed in calculated positions, with C-H = 0.93 Å, Uiso = 1.2Ueq(C). The highest residual electron density peak is located at 0.76 Å from Br1 and the deepest hole is located at 0.69 Å from Br1.

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
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 60% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. Part of the crystal packing of the title compound, viewed along the a axis, showing hydrogen-bonded (dashed lines) dimers.
(E)-3-(Anthracen-9-yl)-1-(4-bromophenyl)prop-2-en-1-one top
Crystal data top
C23H15BrOF(000) = 784
Mr = 387.25Dx = 1.544 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4866 reflections
a = 5.3792 (1) Åθ = 2.1–30.0°
b = 19.1030 (4) ŵ = 2.47 mm1
c = 16.3005 (4) ÅT = 100 K
β = 95.944 (1)°Plate, yellow
V = 1666.02 (6) Å30.57 × 0.27 × 0.15 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
4866 independent reflections
Radiation source: fine-focus sealed tube3803 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 8.33 pixels mm-1θmax = 30.0°, θmin = 2.1°
ω scansh = 77
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 2626
Tmin = 0.331, Tmax = 0.714l = 2222
29994 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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0322P)2 + 1.1607P]
where P = (Fo2 + 2Fc2)/3
4866 reflections(Δ/σ)max = 0.001
226 parametersΔρmax = 0.53 e Å3
0 restraintsΔρmin = 0.54 e Å3
Crystal data top
C23H15BrOV = 1666.02 (6) Å3
Mr = 387.25Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.3792 (1) ŵ = 2.47 mm1
b = 19.1030 (4) ÅT = 100 K
c = 16.3005 (4) Å0.57 × 0.27 × 0.15 mm
β = 95.944 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
4866 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
3803 reflections with I > 2σ(I)
Tmin = 0.331, Tmax = 0.714Rint = 0.036
29994 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.076H-atom parameters constrained
S = 1.02Δρmax = 0.53 e Å3
4866 reflectionsΔρmin = 0.54 e Å3
226 parameters
Special details top

Experimental. The low-temperature 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
Br10.32584 (4)0.344013 (10)0.411244 (11)0.02530 (7)
O10.9073 (2)0.51056 (7)0.74450 (8)0.0213 (3)
C10.7274 (4)0.41439 (9)0.62533 (11)0.0201 (4)
H1A0.88000.40430.65520.024*
C20.6526 (4)0.37631 (10)0.55484 (12)0.0219 (4)
H2A0.75300.34080.53740.026*
C30.4261 (4)0.39203 (9)0.51095 (10)0.0180 (4)
C40.2711 (4)0.44314 (10)0.53719 (11)0.0206 (4)
H4A0.11760.45230.50750.025*
C50.3464 (3)0.48075 (10)0.60836 (10)0.0184 (4)
H5A0.24190.51490.62670.022*
C60.5781 (3)0.46766 (9)0.65244 (10)0.0152 (3)
C70.6813 (3)0.51052 (9)0.72478 (10)0.0159 (3)
C80.5083 (3)0.55087 (9)0.77158 (10)0.0159 (3)
H8A0.33740.54990.75550.019*
C90.5978 (3)0.58858 (9)0.83690 (10)0.0161 (3)
H9A0.77070.59200.84710.019*
C100.4492 (3)0.62533 (9)0.89440 (10)0.0158 (3)
C110.5151 (3)0.61533 (9)0.98020 (10)0.0157 (3)
C120.7151 (4)0.57046 (10)1.01164 (11)0.0195 (4)
H12A0.80150.54520.97490.023*
C130.7822 (4)0.56385 (10)1.09428 (11)0.0219 (4)
H13A0.91490.53491.11320.026*
C140.6506 (4)0.60082 (10)1.15145 (11)0.0220 (4)
H14A0.70020.59701.20760.026*
C150.4527 (4)0.64183 (10)1.12478 (11)0.0224 (4)
H15A0.36520.66481.16310.027*
C160.3767 (3)0.65030 (9)1.03860 (10)0.0169 (3)
C170.1715 (4)0.69108 (9)1.01020 (10)0.0187 (4)
H17A0.07690.71181.04820.022*
C180.1036 (3)0.70178 (9)0.92633 (10)0.0167 (3)
C190.1040 (4)0.74534 (9)0.89840 (11)0.0196 (4)
H19A0.20540.76290.93650.023*
C200.1560 (4)0.76158 (9)0.81740 (11)0.0211 (4)
H20A0.29250.78980.80020.025*
C210.0008 (4)0.73530 (9)0.75909 (11)0.0205 (4)
H21A0.03090.74870.70410.025*
C220.1913 (3)0.69077 (9)0.78224 (10)0.0184 (4)
H22A0.28620.67300.74240.022*
C230.2504 (3)0.67066 (9)0.86689 (10)0.0153 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.03907 (13)0.02093 (10)0.01575 (9)0.00663 (8)0.00217 (7)0.00386 (7)
O10.0137 (7)0.0297 (7)0.0203 (6)0.0009 (5)0.0009 (5)0.0031 (5)
C10.0181 (10)0.0199 (9)0.0219 (9)0.0037 (7)0.0000 (7)0.0002 (7)
C20.0238 (10)0.0180 (9)0.0239 (9)0.0060 (7)0.0029 (7)0.0027 (7)
C30.0238 (10)0.0159 (8)0.0146 (8)0.0052 (7)0.0032 (6)0.0018 (6)
C40.0170 (10)0.0258 (9)0.0182 (8)0.0003 (7)0.0010 (7)0.0016 (7)
C50.0158 (9)0.0228 (9)0.0168 (8)0.0022 (7)0.0020 (6)0.0031 (7)
C60.0155 (9)0.0169 (8)0.0134 (7)0.0013 (6)0.0024 (6)0.0007 (6)
C70.0156 (9)0.0176 (8)0.0148 (7)0.0011 (7)0.0027 (6)0.0005 (6)
C80.0119 (9)0.0206 (8)0.0155 (7)0.0010 (7)0.0022 (6)0.0008 (6)
C90.0133 (9)0.0179 (8)0.0175 (8)0.0016 (7)0.0032 (6)0.0007 (6)
C100.0157 (9)0.0163 (8)0.0155 (8)0.0035 (7)0.0024 (6)0.0019 (6)
C110.0163 (9)0.0155 (8)0.0154 (8)0.0034 (7)0.0018 (6)0.0006 (6)
C120.0195 (10)0.0211 (9)0.0184 (8)0.0005 (7)0.0034 (7)0.0008 (7)
C130.0209 (10)0.0240 (9)0.0202 (8)0.0003 (8)0.0003 (7)0.0026 (7)
C140.0292 (11)0.0223 (9)0.0140 (8)0.0036 (8)0.0004 (7)0.0005 (7)
C150.0307 (11)0.0227 (9)0.0141 (8)0.0017 (8)0.0042 (7)0.0017 (7)
C160.0210 (9)0.0144 (8)0.0156 (8)0.0040 (7)0.0036 (6)0.0015 (6)
C170.0225 (10)0.0168 (8)0.0175 (8)0.0003 (7)0.0054 (7)0.0032 (6)
C180.0182 (9)0.0142 (8)0.0178 (8)0.0032 (7)0.0021 (6)0.0015 (6)
C190.0193 (10)0.0156 (8)0.0244 (9)0.0002 (7)0.0050 (7)0.0024 (7)
C200.0200 (10)0.0160 (8)0.0266 (9)0.0010 (7)0.0018 (7)0.0006 (7)
C210.0216 (10)0.0209 (9)0.0182 (8)0.0033 (7)0.0016 (7)0.0014 (7)
C220.0192 (10)0.0191 (9)0.0168 (8)0.0029 (7)0.0020 (6)0.0020 (7)
C230.0155 (9)0.0154 (8)0.0150 (7)0.0048 (6)0.0013 (6)0.0018 (6)
Geometric parameters (Å, º) top
Br1—C31.8954 (17)C12—C131.364 (2)
O1—C71.225 (2)C12—H12A0.93
C1—C21.384 (3)C13—C141.416 (3)
C1—C61.396 (2)C13—H13A0.93
C1—H1A0.93C14—C151.356 (3)
C2—C31.380 (3)C14—H14A0.93
C2—H2A0.93C15—C161.431 (2)
C3—C41.380 (3)C15—H15A0.93
C4—C51.389 (2)C16—C171.391 (3)
C4—H4A0.93C17—C181.393 (2)
C5—C61.395 (2)C17—H17A0.93
C5—H5A0.93C18—C191.429 (3)
C6—C71.495 (2)C18—C231.440 (2)
C7—C81.480 (2)C19—C201.357 (3)
C8—C91.333 (2)C19—H19A0.93
C8—H8A0.93C20—C211.420 (3)
C9—C101.472 (2)C20—H20A0.93
C9—H9A0.93C21—C221.361 (3)
C10—C231.413 (3)C21—H21A0.93
C10—C111.420 (2)C22—C231.436 (2)
C11—C121.428 (3)C22—H22A0.93
C11—C161.433 (2)
C2—C1—C6121.23 (17)C11—C12—H12A119.3
C2—C1—H1A119.4C12—C13—C14120.32 (18)
C6—C1—H1A119.4C12—C13—H13A119.8
C3—C2—C1118.75 (17)C14—C13—H13A119.8
C3—C2—H2A120.6C15—C14—C13120.41 (17)
C1—C2—H2A120.6C15—C14—H14A119.8
C4—C3—C2121.49 (16)C13—C14—H14A119.8
C4—C3—Br1118.73 (14)C14—C15—C16121.00 (17)
C2—C3—Br1119.78 (14)C14—C15—H15A119.5
C3—C4—C5119.44 (17)C16—C15—H15A119.5
C3—C4—H4A120.3C17—C16—C15121.78 (16)
C5—C4—H4A120.3C17—C16—C11119.28 (16)
C4—C5—C6120.34 (17)C15—C16—C11118.94 (17)
C4—C5—H5A119.8C16—C17—C18121.81 (16)
C6—C5—H5A119.8C16—C17—H17A119.1
C5—C6—C1118.69 (16)C18—C17—H17A119.1
C5—C6—C7123.18 (16)C17—C18—C19120.98 (16)
C1—C6—C7118.04 (16)C17—C18—C23119.57 (16)
O1—C7—C8121.62 (16)C19—C18—C23119.41 (15)
O1—C7—C6119.02 (15)C20—C19—C18121.24 (17)
C8—C7—C6119.35 (15)C20—C19—H19A119.4
C9—C8—C7119.93 (16)C18—C19—H19A119.4
C9—C8—H8A120.0C19—C20—C21119.62 (18)
C7—C8—H8A120.0C19—C20—H20A120.2
C8—C9—C10126.25 (17)C21—C20—H20A120.2
C8—C9—H9A116.9C22—C21—C20121.16 (16)
C10—C9—H9A116.9C22—C21—H21A119.4
C23—C10—C11119.94 (15)C20—C21—H21A119.4
C23—C10—C9122.24 (15)C21—C22—C23121.31 (17)
C11—C10—C9117.80 (16)C21—C22—H22A119.3
C10—C11—C12122.43 (16)C23—C22—H22A119.3
C10—C11—C16119.84 (16)C10—C23—C22123.65 (16)
C12—C11—C16117.72 (15)C10—C23—C18119.29 (15)
C13—C12—C11121.49 (17)C22—C23—C18116.99 (16)
C13—C12—H12A119.3
C6—C1—C2—C30.3 (3)C13—C14—C15—C161.8 (3)
C1—C2—C3—C41.9 (3)C14—C15—C16—C17178.78 (18)
C1—C2—C3—Br1176.90 (14)C14—C15—C16—C110.8 (3)
C2—C3—C4—C51.4 (3)C10—C11—C16—C173.0 (3)
Br1—C3—C4—C5177.43 (14)C12—C11—C16—C17176.19 (16)
C3—C4—C5—C60.8 (3)C10—C11—C16—C15177.41 (16)
C4—C5—C6—C12.4 (3)C12—C11—C16—C153.4 (2)
C4—C5—C6—C7174.05 (17)C15—C16—C17—C18177.22 (17)
C2—C1—C6—C51.9 (3)C11—C16—C17—C183.2 (3)
C2—C1—C6—C7174.75 (17)C16—C17—C18—C19178.36 (17)
C5—C6—C7—O1158.07 (17)C16—C17—C18—C230.7 (3)
C1—C6—C7—O118.4 (2)C17—C18—C19—C20173.37 (17)
C5—C6—C7—C822.9 (2)C23—C18—C19—C204.3 (3)
C1—C6—C7—C8160.59 (16)C18—C19—C20—C210.4 (3)
O1—C7—C8—C90.1 (3)C19—C20—C21—C223.8 (3)
C6—C7—C8—C9179.10 (16)C20—C21—C22—C232.3 (3)
C7—C8—C9—C10173.26 (16)C11—C10—C23—C22171.79 (16)
C8—C9—C10—C2350.2 (3)C9—C10—C23—C226.7 (3)
C8—C9—C10—C11131.30 (19)C11—C10—C23—C185.1 (3)
C23—C10—C11—C12179.68 (17)C9—C10—C23—C18176.46 (16)
C9—C10—C11—C121.1 (3)C21—C22—C23—C10179.25 (18)
C23—C10—C11—C161.1 (3)C21—C22—C23—C182.3 (3)
C9—C10—C11—C16179.69 (16)C17—C18—C23—C104.9 (3)
C10—C11—C12—C13177.21 (17)C19—C18—C23—C10177.42 (16)
C16—C11—C12—C133.6 (3)C17—C18—C23—C22172.15 (16)
C11—C12—C13—C141.1 (3)C19—C18—C23—C225.5 (2)
C12—C13—C14—C151.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···O1i0.932.423.308 (2)159
C13—H13A···O1ii0.932.573.288 (2)135
C21—H21A···Br1iii0.932.933.4722 (19)119
C9—H9A···Cg1iv0.932.833.4479 (18)125
Symmetry codes: (i) x1, y, z; (ii) x+2, y+1, z+2; (iii) x, y+1, z+1; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC23H15BrO
Mr387.25
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)5.3792 (1), 19.1030 (4), 16.3005 (4)
β (°) 95.944 (1)
V3)1666.02 (6)
Z4
Radiation typeMo Kα
µ (mm1)2.47
Crystal size (mm)0.57 × 0.27 × 0.15
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.331, 0.714
No. of measured, independent and
observed [I > 2σ(I)] reflections
29994, 4866, 3803
Rint0.036
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.076, 1.02
No. of reflections4866
No. of parameters226
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.53, 0.54

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···O1i0.932.423.308 (2)159
C13—H13A···O1ii0.932.573.288 (2)135
C21—H21A···Br1iii0.932.933.4722 (19)119
C9—H9A···Cg1iv0.932.833.4479 (18)125
Symmetry codes: (i) x1, y, z; (ii) x+2, y+1, z+2; (iii) x, y+1, z+1; (iv) x+1, y, z.
 

Footnotes

This paper is dedicated to the late Her Royal Highness Princess Galyani Vadhana Krom Luang Naradhiwas Rajanagarindra for her patronage of Science in Thailand.

Additional correspondence author, e-mail: hkfun@usm.my.

Acknowledgements

Financial support from the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Commision on Higher Education, Ministry of Education, Thailand, is gratefully acknowledged. The authors also thank the Thailand Research Fund (TRF) and the Prince of Songkla University for financial support, and the Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

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Volume 65| Part 2| February 2009| Pages o420-o421
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