organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 4| April 2012| Pages o1269-o1270

4-Bromo-N-phenyl­benzamide

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
*Correspondence e-mail: hkfun@usm.my

(Received 20 March 2012; accepted 28 March 2012; online 31 March 2012)

The mol­ecule of the title benzamide derivative, C13H10BrNO, is twisted with the dihedral angle between the phenyl and 4-bromo­phenyl rings being 58.63 (9)°. The central N—C=O plane makes dihedral angles of 30.2 (2) and 29.2 (2)° with the phenyl and 4-bromo­phenyl rings, respectively. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds into chains along [100]. C—H⋯π contacts combine with the N—H⋯O hydrogen bonds, to form a three-dimensional network.

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: Johnston & Taylor (2011[Johnston, D. H. & Taylor, C. R. (2011). Acta Cryst. E67, o2735.]); Li & Cui (2011[Li, H.-L. & Cui, J.-T. (2011). Acta Cryst. E67, o1596.]); Saeed et al. (2008[Saeed, A., Hussain, S. & Flörke, U. (2008). Acta Cryst. E64, o705.]); Sripet et al. (2012[Sripet, W., Chantrapromma, S., Ruanwas, P. & Fun, H.-K. (2012). Acta Cryst. E68, o1234.]). For background to and applications of benzamide derivatives, see: Boonleang & Tanthana (2010[Boonleang, J. & Tanthana, C. (2010). Songklanakarin J. Sci. Technol. 32, 605-611.]); Brown et al. (1991[Brown, J. M., Lemmon, M. J., Horsman, M. R. & Lee, W. W. (1991). Int. J. Radiat. Biol. 59, 739-748.]); Hu et al. (2008[Hu, W.-P., Yu, H.-S., Chen, Y.-R., Tsai, Y.-M., Chen, Y.-K., Liao, C.-C., Chang, L.-S. & Wang, J.-J. (2008). Bioorg. Med. Chem. 16, 5295-5302.]); Mobi­nikh­aledi et al. (2006[Mobinikhaledi, A., Forughifar, N., Shariatzadeh, S. M. & Fallah, M. (2006). Heterocycl. Commun. 12, 427-430.]); Olsson et al. (2002[Olsson, A. R., Lindgren, H., Pero, R. W. & Leanderson, T. (2002). Br. J. Cancer, 86, 971-978.]); World Health Organization (2003[World Health Organization (2003). Pharmaceuticals: Restriction in Use and Availability, Essential Drugs and Medicines Policy-Quality Assurance and Safely: Medicines Health Technology and Pharmaceuticals. Geneva, Switzerland.]); Xu et al. (2009[Xu, J., Lecanu, L., Tan, M., Greeson, J. & Papadopoulos, V. (2009). Molecules, 14, 3392-3410.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C13H10BrNO

  • Mr = 276.12

  • Triclinic, [P \overline 1]

  • a = 5.3552 (2) Å

  • b = 7.6334 (2) Å

  • c = 13.9956 (5) Å

  • α = 105.757 (3)°

  • β = 100.585 (3)°

  • γ = 90.086 (2)°

  • V = 540.45 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 3.78 mm−1

  • T = 100 K

  • 0.29 × 0.09 × 0.07 mm

Data collection
  • Bruker 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 = 0.406, Tmax = 0.791

  • 11303 measured reflections

  • 3844 independent reflections

  • 3193 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.076

  • S = 1.08

  • 3844 reflections

  • 149 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.66 e Å−3

  • Δρmin = −0.68 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N1⋯O1i 0.84 (3) 2.37 (3) 3.150 (2) 156 (2)
C2—H2ACg2ii 0.95 2.77 3.4855 (19) 132
C5—H5ACg2iii 0.95 2.70 3.4258 (19) 134
C10—H10ACg1iv 0.95 2.90 3.5444 (19) 126
C13—H13ACg1v 0.95 2.84 3.4950 (19) 127
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y, -z; (iii) -x+1, -y+1, -z; (iv) -x+1, -y, -z; (v) -x+2, -y+1, -z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Benzamides are recognised as one of the bioactive skeletons, and some benzamide derivatives exhibit various potent pharmaceutical activities (Brown et al., 1991; Hu et al., 2008). They have been developed as anti-tumor (Olsson et al., 2002), antibacterial (Mobinikhaledi et al., 2006) and anti-Alzheimer's agents (Xu et al., 2009). Cisapride (CIS) is an effective benzamide derived drug which can act as a gastrointestinal prokinetic agent. It also has restricted usage for the treatment of gastroesophageal reflux disease in some countries (World Health Organization, 2003) due to its cardiac side effects. The formulation of a more stable CIS oral suspension was studied (Boonleang & Tanthana, 2010). We have synthesized several N-phenylbenzamide derivatives in order to evaluate their antibacterial and anti-Alzheimer's activities, and the structure of the title benzamide derivative (I) is reported here.

The molecule of the title benzamide derivative (Fig. 1), C13H10BrNO, is twisted with the dihedral angle between the phenyl and 4-bromophenyl rings being 58.63 (9)°. The central N-C=O plane is twisted with respect to the two neighbouring ring planes forming dihedral angles of 30.2 (2) and 29.2 (2) ° with the phenyl and 4-bromophenyl rings respectively, and with torsion angles C2–C1–C7–O1 = -28.1 (3)° and C7–N1–C8–C13 = -30.2 (3)°. Bond distances are within normal ranges (Allen et al., 1987) and are comparable to those found in related structures (Johnston & Taylor, 2011; Li & Cui, 2011; Saeed et al., 2008; Sripet et al., 2012).

In the crystal packing (Fig. 2), the molecules are linked by N—H···O hydrogen bonds (Table 1) into chains along the [100] direction. C—H···π contacts involving H atoms from both the phenyl and 4-bromophenyl rings combine with the N—H···O hydrogen bonds to form a 3-dimensional network (Table 1).

Related literature top

For bond-length data, see: Allen et al. (1987). For related structures, see: Johnston & Taylor (2011); Li & Cui (2011); Saeed et al. (2008); Sripet et al. (2012). For background to and applications of benzamide derivatives, see: Boonleang & Tanthana (2010); Brown et al. (1991); Hu et al. (2008); Mobinikhaledi et al. (2006); Olsson et al. (2002); World Health Organization (2003); Xu et al. (2009). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

To the solution of 4-bromobenzoyl chloride (0.20 g, 0.91 mmol) in acetone (10 ml), aniline (0.12 ml, 1.37 mmol) was added and refluxed for 6 h. After the reaction was completed, a gray solid mass formed which was filtered and washed with distilled water. Colorless needle-shaped single crystals of the title compound suitable for X-ray structure determination were recrystallized from acetone/CH3OH (1:1 v/v) by slow evaporation of the solvent at room temperature over a week, Mp. 474-475 K.

Refinement top

The amide H atom was located in a difference map and refined isotropically. The aromatic H atoms were positioned geometrically and allowed to ride on their parent atoms, with d(C-H) = 0.95 Å and the Uiso values were constrained to be 1.2Ueq of the carrier atom.

Structure description top

Benzamides are recognised as one of the bioactive skeletons, and some benzamide derivatives exhibit various potent pharmaceutical activities (Brown et al., 1991; Hu et al., 2008). They have been developed as anti-tumor (Olsson et al., 2002), antibacterial (Mobinikhaledi et al., 2006) and anti-Alzheimer's agents (Xu et al., 2009). Cisapride (CIS) is an effective benzamide derived drug which can act as a gastrointestinal prokinetic agent. It also has restricted usage for the treatment of gastroesophageal reflux disease in some countries (World Health Organization, 2003) due to its cardiac side effects. The formulation of a more stable CIS oral suspension was studied (Boonleang & Tanthana, 2010). We have synthesized several N-phenylbenzamide derivatives in order to evaluate their antibacterial and anti-Alzheimer's activities, and the structure of the title benzamide derivative (I) is reported here.

The molecule of the title benzamide derivative (Fig. 1), C13H10BrNO, is twisted with the dihedral angle between the phenyl and 4-bromophenyl rings being 58.63 (9)°. The central N-C=O plane is twisted with respect to the two neighbouring ring planes forming dihedral angles of 30.2 (2) and 29.2 (2) ° with the phenyl and 4-bromophenyl rings respectively, and with torsion angles C2–C1–C7–O1 = -28.1 (3)° and C7–N1–C8–C13 = -30.2 (3)°. Bond distances are within normal ranges (Allen et al., 1987) and are comparable to those found in related structures (Johnston & Taylor, 2011; Li & Cui, 2011; Saeed et al., 2008; Sripet et al., 2012).

In the crystal packing (Fig. 2), the molecules are linked by N—H···O hydrogen bonds (Table 1) into chains along the [100] direction. C—H···π contacts involving H atoms from both the phenyl and 4-bromophenyl rings combine with the N—H···O hydrogen bonds to form a 3-dimensional network (Table 1).

For bond-length data, see: Allen et al. (1987). For related structures, see: Johnston & Taylor (2011); Li & Cui (2011); Saeed et al. (2008); Sripet et al. (2012). For background to and applications of benzamide derivatives, see: Boonleang & Tanthana (2010); Brown et al. (1991); Hu et al. (2008); Mobinikhaledi et al. (2006); Olsson et al. (2002); World Health Organization (2003); Xu et al. (2009). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (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, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed along the b axis, showing the molecular chains along the [100] direction. N—H···O hydrogen bonds were drawn as dashed lines.
4-Bromo-N-phenylbenzamide top
Crystal data top
C13H10BrNOZ = 2
Mr = 276.12F(000) = 276
Triclinic, P1Dx = 1.697 Mg m3
Hall symbol: -P 1Melting point = 474–475 K
a = 5.3552 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.6334 (2) ÅCell parameters from 3844 reflections
c = 13.9956 (5) Åθ = 2.8–32.5°
α = 105.757 (3)°µ = 3.78 mm1
β = 100.585 (3)°T = 100 K
γ = 90.086 (2)°Needle, colorless
V = 540.45 (3) Å30.29 × 0.09 × 0.07 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
3844 independent reflections
Radiation source: sealed tube3193 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 32.5°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 78
Tmin = 0.406, Tmax = 0.791k = 1111
11303 measured reflectionsl = 2121
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 atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0335P)2 + 0.2642P]
where P = (Fo2 + 2Fc2)/3
3844 reflections(Δ/σ)max = 0.001
149 parametersΔρmax = 0.66 e Å3
0 restraintsΔρmin = 0.68 e Å3
Crystal data top
C13H10BrNOγ = 90.086 (2)°
Mr = 276.12V = 540.45 (3) Å3
Triclinic, P1Z = 2
a = 5.3552 (2) ÅMo Kα radiation
b = 7.6334 (2) ŵ = 3.78 mm1
c = 13.9956 (5) ÅT = 100 K
α = 105.757 (3)°0.29 × 0.09 × 0.07 mm
β = 100.585 (3)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
3844 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
3193 reflections with I > 2σ(I)
Tmin = 0.406, Tmax = 0.791Rint = 0.032
11303 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.076H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.66 e Å3
3844 reflectionsΔρmin = 0.68 e Å3
149 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br10.91443 (4)0.72493 (3)0.467544 (14)0.01790 (7)
O11.1259 (3)0.2407 (2)0.00304 (11)0.0175 (3)
N10.6913 (3)0.2128 (2)0.03111 (12)0.0119 (3)
H1N10.564 (5)0.226 (4)0.003 (2)0.020 (6)*
C10.9088 (4)0.3807 (2)0.13585 (13)0.0112 (3)
C21.1145 (4)0.3763 (2)0.21293 (14)0.0126 (3)
H2A1.25330.30370.19720.015*
C31.1178 (4)0.4768 (2)0.31221 (14)0.0134 (3)
H3A1.25650.47280.36460.016*
C40.9141 (4)0.5833 (2)0.33308 (13)0.0126 (3)
C50.7083 (4)0.5916 (2)0.25806 (14)0.0130 (3)
H5A0.57200.66660.27390.016*
C60.7057 (4)0.4879 (2)0.15909 (13)0.0119 (3)
H6A0.56490.49020.10720.014*
C70.9210 (4)0.2720 (2)0.03006 (14)0.0128 (3)
C80.6473 (4)0.1133 (2)0.13458 (13)0.0112 (3)
C90.4262 (4)0.0002 (2)0.17278 (14)0.0124 (3)
H9A0.31610.01310.12890.015*
C100.3667 (4)0.0932 (2)0.27495 (14)0.0138 (3)
H10A0.21600.17010.30050.017*
C110.5252 (4)0.0749 (2)0.33980 (13)0.0138 (3)
H11A0.48320.13810.40970.017*
C120.7467 (4)0.0368 (3)0.30173 (14)0.0141 (3)
H12A0.85670.04870.34590.017*
C130.8091 (4)0.1317 (2)0.19935 (14)0.0125 (3)
H13A0.96030.20800.17400.015*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02581 (12)0.01545 (9)0.01116 (9)0.00385 (7)0.00550 (7)0.00021 (6)
O10.0126 (7)0.0236 (7)0.0141 (6)0.0029 (6)0.0038 (5)0.0005 (5)
N10.0110 (7)0.0129 (7)0.0117 (7)0.0007 (6)0.0045 (6)0.0016 (5)
C10.0114 (8)0.0100 (7)0.0121 (7)0.0008 (6)0.0039 (6)0.0020 (6)
C20.0107 (8)0.0118 (7)0.0148 (8)0.0018 (6)0.0033 (6)0.0021 (6)
C30.0147 (9)0.0133 (8)0.0119 (8)0.0007 (7)0.0021 (6)0.0033 (6)
C40.0171 (9)0.0097 (7)0.0110 (7)0.0002 (7)0.0057 (6)0.0010 (6)
C50.0142 (9)0.0108 (7)0.0148 (8)0.0022 (7)0.0063 (7)0.0027 (6)
C60.0125 (8)0.0111 (7)0.0116 (7)0.0014 (6)0.0026 (6)0.0021 (6)
C70.0136 (9)0.0127 (8)0.0121 (8)0.0021 (7)0.0029 (6)0.0034 (6)
C80.0135 (8)0.0090 (7)0.0115 (7)0.0028 (6)0.0031 (6)0.0031 (6)
C90.0115 (8)0.0109 (7)0.0154 (8)0.0017 (6)0.0042 (6)0.0037 (6)
C100.0116 (9)0.0129 (8)0.0159 (8)0.0007 (7)0.0019 (7)0.0030 (6)
C110.0148 (9)0.0131 (8)0.0109 (7)0.0027 (7)0.0015 (6)0.0004 (6)
C120.0154 (9)0.0148 (8)0.0137 (8)0.0037 (7)0.0060 (7)0.0045 (6)
C130.0124 (9)0.0116 (7)0.0140 (8)0.0015 (7)0.0040 (6)0.0033 (6)
Geometric parameters (Å, º) top
Br1—C41.8985 (18)C5—H5A0.9500
O1—C71.228 (2)C6—H6A0.9500
N1—C71.361 (2)C8—C91.395 (3)
N1—C81.417 (2)C8—C131.396 (3)
N1—H1N10.84 (3)C9—C101.390 (3)
C1—C61.395 (3)C9—H9A0.9500
C1—C21.401 (2)C10—C111.384 (3)
C1—C71.501 (2)C10—H10A0.9500
C2—C31.390 (3)C11—C121.391 (3)
C2—H2A0.9500C11—H11A0.9500
C3—C41.388 (3)C12—C131.396 (3)
C3—H3A0.9500C12—H12A0.9500
C4—C51.390 (3)C13—H13A0.9500
C5—C61.394 (2)
C7—N1—C8126.73 (17)O1—C7—N1123.92 (17)
C7—N1—H1N1116.5 (18)O1—C7—C1121.13 (17)
C8—N1—H1N1116.4 (18)N1—C7—C1114.94 (16)
C6—C1—C2119.54 (16)C9—C8—C13119.69 (16)
C6—C1—C7122.67 (16)C9—C8—N1117.73 (17)
C2—C1—C7117.76 (16)C13—C8—N1122.50 (17)
C3—C2—C1120.71 (17)C10—C9—C8120.15 (18)
C3—C2—H2A119.6C10—C9—H9A119.9
C1—C2—H2A119.6C8—C9—H9A119.9
C4—C3—C2118.53 (17)C11—C10—C9120.53 (18)
C4—C3—H3A120.7C11—C10—H10A119.7
C2—C3—H3A120.7C9—C10—H10A119.7
C3—C4—C5122.06 (17)C10—C11—C12119.40 (17)
C3—C4—Br1119.66 (14)C10—C11—H11A120.3
C5—C4—Br1118.28 (14)C12—C11—H11A120.3
C4—C5—C6118.79 (17)C11—C12—C13120.79 (18)
C4—C5—H5A120.6C11—C12—H12A119.6
C6—C5—H5A120.6C13—C12—H12A119.6
C5—C6—C1120.35 (17)C8—C13—C12119.43 (17)
C5—C6—H6A119.8C8—C13—H13A120.3
C1—C6—H6A119.8C12—C13—H13A120.3
C6—C1—C2—C30.2 (3)C2—C1—C7—O128.1 (3)
C7—C1—C2—C3178.64 (17)C6—C1—C7—N129.9 (3)
C1—C2—C3—C40.7 (3)C2—C1—C7—N1151.72 (17)
C2—C3—C4—C50.1 (3)C7—N1—C8—C9153.01 (18)
C2—C3—C4—Br1179.15 (14)C7—N1—C8—C1330.2 (3)
C3—C4—C5—C60.8 (3)C13—C8—C9—C100.3 (3)
Br1—C4—C5—C6179.88 (14)N1—C8—C9—C10176.59 (16)
C4—C5—C6—C11.3 (3)C8—C9—C10—C110.1 (3)
C2—C1—C6—C50.7 (3)C9—C10—C11—C120.5 (3)
C7—C1—C6—C5177.57 (17)C10—C11—C12—C130.6 (3)
C8—N1—C7—O12.4 (3)C9—C8—C13—C120.2 (3)
C8—N1—C7—C1177.82 (16)N1—C8—C13—C12176.50 (16)
C6—C1—C7—O1150.22 (19)C11—C12—C13—C80.2 (3)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O1i0.84 (3)2.37 (3)3.150 (2)156 (2)
C13—H13A···O10.952.422.923 (2)113
C2—H2A···Cg2ii0.952.773.4855 (19)132
C5—H5A···Cg2iii0.952.703.4258 (19)134
C10—H10A···Cg1iv0.952.903.5444 (19)126
C13—H13A···Cg1v0.952.843.4950 (19)127
Symmetry codes: (i) x1, y, z; (ii) x+2, y, z; (iii) x+1, y+1, z; (iv) x+1, y, z; (v) x+2, y+1, z.

Experimental details

Crystal data
Chemical formulaC13H10BrNO
Mr276.12
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)5.3552 (2), 7.6334 (2), 13.9956 (5)
α, β, γ (°)105.757 (3), 100.585 (3), 90.086 (2)
V3)540.45 (3)
Z2
Radiation typeMo Kα
µ (mm1)3.78
Crystal size (mm)0.29 × 0.09 × 0.07
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.406, 0.791
No. of measured, independent and
observed [I > 2σ(I)] reflections
11303, 3844, 3193
Rint0.032
(sin θ/λ)max1)0.756
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.076, 1.08
No. of reflections3844
No. of parameters149
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.66, 0.68

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1N1···O1i0.84 (3)2.37 (3)3.150 (2)156 (2)
C2—H2A···Cg2ii0.952.773.4855 (19)132
C5—H5A···Cg2iii0.952.703.4258 (19)134
C10—H10A···Cg1iv0.952.903.5444 (19)126
C13—H13A···Cg1v0.952.843.4950 (19)127
Symmetry codes: (i) x1, y, z; (ii) x+2, y, z; (iii) x+1, y+1, z; (iv) x+1, y, z; (v) x+2, y+1, z.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5085-2009. Additional correspondence author, e-mail: suchada.c@psu.ac.th.

Acknowledgements

The authors thank Prince of Songkla University for financial support through the Crystal Materials Research Unit. NB also thanks Prince of Songkla University for a postdoctoral fellowship. The authors also thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CSD CrossRef Web of Science
First citationBoonleang, J. & Tanthana, C. (2010). Songklanakarin J. Sci. Technol. 32, 605–611.  CAS
First citationBrown, J. M., Lemmon, M. J., Horsman, M. R. & Lee, W. W. (1991). Int. J. Radiat. Biol. 59, 739–748.  CrossRef PubMed CAS Web of Science
First citationBruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.  CrossRef CAS Web of Science IUCr Journals
First citationHu, W.-P., Yu, H.-S., Chen, Y.-R., Tsai, Y.-M., Chen, Y.-K., Liao, C.-C., Chang, L.-S. & Wang, J.-J. (2008). Bioorg. Med. Chem. 16, 5295–5302.  Web of Science CrossRef PubMed CAS
First citationJohnston, D. H. & Taylor, C. R. (2011). Acta Cryst. E67, o2735.  Web of Science CSD CrossRef IUCr Journals
First citationLi, H.-L. & Cui, J.-T. (2011). Acta Cryst. E67, o1596.  Web of Science CSD CrossRef IUCr Journals
First citationMobinikhaledi, A., Forughifar, N., Shariatzadeh, S. M. & Fallah, M. (2006). Heterocycl. Commun. 12, 427–430.  CrossRef CAS
First citationOlsson, A. R., Lindgren, H., Pero, R. W. & Leanderson, T. (2002). Br. J. Cancer, 86, 971–978.  Web of Science CrossRef PubMed CAS
First citationSaeed, A., Hussain, S. & Flörke, U. (2008). Acta Cryst. E64, o705.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals
First citationSripet, W., Chantrapromma, S., Ruanwas, P. & Fun, H.-K. (2012). Acta Cryst. E68, o1234.  CSD CrossRef IUCr Journals
First citationWorld Health Organization (2003). Pharmaceuticals: Restriction in Use and Availability, Essential Drugs and Medicines Policy-Quality Assurance and Safely: Medicines Health Technology and Pharmaceuticals. Geneva, Switzerland.
First citationXu, J., Lecanu, L., Tan, M., Greeson, J. & Papadopoulos, V. (2009). Molecules, 14, 3392–3410.  Web of Science CrossRef PubMed CAS

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 4| April 2012| Pages o1269-o1270
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds