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ISSN: 2056-9890

2-(5-Bromo-2-hy­droxy­phen­yl)-1,2-di­hydro­quinazolin-4(3H)-one

aDepartment of Chemistry, Sharif University of Technology, PO Box 11155-8639, Tehran, Iran, and bDepartment of Chemistry, Loughborough University, Leicestershire LE11 3TU, England
*Correspondence e-mail: dboghaei@sharif.edu

(Received 8 October 2008; accepted 30 October 2008; online 24 December 2008)

The asymmetric unit of the title compound, C14H11BrN2O2, contains two independent mol­ecules connected into a dimer by inter­molecular N—H⋯O hydrogen bonds involving the amine and carbonyl groups. The dimers are further connected by O—H⋯O hydrogen bonds, forming chains running parallel to the a axis, which are stabilized through ππ stacking inter­actions, with a centroid–centroid distance of 3.679 (8) Å. The dihedral angle between the two aromatic rings is 89.2 (4)°.

Related literature

For general background to the chemistry of quinazolinone derivatives, see: Liu (2008[Liu, G. (2008). Acta Cryst. E64, o1677.]); Goto et al. (1993[Goto, S., Tsuboi, H. & Kagara, K. (1993). Chem. Express, 8, 761-764.]); Mohri (2001[Mohri, S. J. (2001). Synth. Org. Chem. Jpn, 59, 514-515.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C14H11BrN2O2

  • Mr = 319.16

  • Triclinic, [P \overline 1]

  • a = 8.8392 (5) Å

  • b = 11.2252 (7) Å

  • c = 13.8817 (8) Å

  • α = 73.0392 (9)°

  • β = 75.9620 (9)°

  • γ = 85.0936 (9)°

  • V = 1277.95 (13) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 3.21 mm−1

  • T = 150 (2) K

  • 0.21 × 0.12 × 0.07 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.552, Tmax = 0.806

  • 13015 measured reflections

  • 6129 independent reflections

  • 4580 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.099

  • S = 1.02

  • 6129 reflections

  • 343 parameters

  • H-atom parameters constrained

  • Δρmax = 0.64 e Å−3

  • Δρmin = −0.70 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2A—H2NA⋯O1B 0.95 1.97 2.897 (3) 165
N2B—H2NB⋯O1A 0.91 2.05 2.914 (3) 157
O2A—H2OA⋯O1Ai 0.85 1.90 2.701 (3) 157
O2B—H2OB⋯O1Bii 0.85 1.86 2.691 (3) 165
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Quinazolinone derivatives are of interest because of their biological activity, and have been widely used as key compounds in medicinal drugs (Goto et al., 1993; Mohri, 2001). We herein report the crystal structure of 1,2-dihydro-2-(5-bromo-2-hydroxybenzene)-4(3H)-quinazolinone.

The asymmentric unit of the title compound (Fig. 1) contains two crystallographically independent molecules, which are linked into a dimer by a pair of intermolecular N—H···O hydrogen bonds (Table 1), generating a ring of graph set R22(8) (Bernstein et al., 1995). Bond lengths and angles are within normal ranges. The dimers are further connected by O—H···O hydrogen bonding interactions to form chains running parallel to the a axis (Figures 2). The chains are stabilized by ππ stacking interactions involving adjacent 5-bromo-2-hydroxybenzene rings, with a centroid-centroid separation of 3.679 (8) Å, a perpendicular interplanar distance of 3.561 (8) Å and a centroid···centroid offset of 0.924 (6) Å.

Related literature top

For general background to the chemistry of quinazolinone derivatives, see: Liu (2008); Goto et al. (1993); Mohri (2001). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was synthesized by adding 5-bromo-2-hydroxybenzaldehyde (2 mmol, 402 mg) to a solution of 2-aminobenzamide (2 mmol, 272 mg) and manganese acetate (0.02 mmol, 4.90 mg) in ethanol (20 ml). The mixture was refluxed with stirring for 5 h. The resultant yellow solution was filtered. Yellow single crystals of the title compound suitable for X-ray structure determination were recrystallized from a mixture of water/ethanol (2:1 v/v) by slow evaporation of the solvents at room temperature over several days.

Refinement top

All H atoms atoms were placed in calculated positions and refined using the riding model approximation, with C—H = 0.95-1.0 Å, O—H = 0.85 Å, N—H = 0.89 Å and with Uiso(H) = 1.2Ueq(C). The isotropic thermal parameter of the hydrogen atoms bound to the N and O atoms was fixed at 0.04 Å2.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. Crystal packing of the title compound viewed along the a axis with hydrogen atoms omitted for clarity. Hydrogen bonds are shown as dashed lines.
2-(5-Bromo-2-hydroxyphenyl)-1,2-dihydroquinazolin-4(3H)-one top
Crystal data top
C14H11BrN2O2Z = 4
Mr = 319.16F(000) = 640
Triclinic, P1Dx = 1.659 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.8392 (5) ÅCell parameters from 3058 reflections
b = 11.2252 (7) Åθ = 2.4–25.8°
c = 13.8817 (8) ŵ = 3.22 mm1
α = 73.0392 (9)°T = 150 K
β = 75.9620 (9)°Block, yellow
γ = 85.0936 (9)°0.21 × 0.12 × 0.07 mm
V = 1277.95 (13) Å3
Data collection top
Bruker APEXII CCD
diffractometer
6129 independent reflections
Radiation source: fine-focus sealed tube4580 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ϕ and ω scansθmax = 28.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1111
Tmin = 0.552, Tmax = 0.806k = 1414
13015 measured reflectionsl = 1818
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0415P)2 + 0.6583P]
where P = (Fo2 + 2Fc2)/3
6129 reflections(Δ/σ)max = 0.001
343 parametersΔρmax = 0.64 e Å3
0 restraintsΔρmin = 0.71 e Å3
Crystal data top
C14H11BrN2O2γ = 85.0936 (9)°
Mr = 319.16V = 1277.95 (13) Å3
Triclinic, P1Z = 4
a = 8.8392 (5) ÅMo Kα radiation
b = 11.2252 (7) ŵ = 3.22 mm1
c = 13.8817 (8) ÅT = 150 K
α = 73.0392 (9)°0.21 × 0.12 × 0.07 mm
β = 75.9620 (9)°
Data collection top
Bruker APEXII CCD
diffractometer
6129 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
4580 reflections with I > 2σ(I)
Tmin = 0.552, Tmax = 0.806Rint = 0.035
13015 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.099H-atom parameters constrained
S = 1.03Δρmax = 0.64 e Å3
6129 reflectionsΔρmin = 0.71 e Å3
343 parameters
Special details top

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
N1A0.0154 (3)0.1619 (2)0.82388 (19)0.0233 (5)
C1A0.1438 (3)0.2154 (3)0.7715 (2)0.0226 (6)
C2A0.1414 (4)0.3350 (3)0.7594 (2)0.0274 (7)
H2A0.04870.38220.78740.033*
C3A0.2724 (4)0.3839 (3)0.7072 (2)0.0308 (7)
H3A0.26930.46520.70000.037*
C4A0.4098 (4)0.3167 (3)0.6646 (2)0.0301 (7)
H4A0.49810.35060.62620.036*
C5A0.4164 (3)0.2011 (3)0.6785 (2)0.0260 (7)
H5A0.51030.15540.65080.031*
C6A0.2848 (3)0.1506 (3)0.7335 (2)0.0221 (6)
C7A0.2963 (3)0.0355 (3)0.7617 (2)0.0219 (6)
O1A0.4227 (2)0.0103 (2)0.75507 (16)0.0260 (5)
N2A0.1608 (3)0.0141 (2)0.80201 (19)0.0227 (5)
C8A0.0102 (3)0.0267 (3)0.7988 (2)0.0224 (6)
H8A0.07070.00300.85450.027*
C9A0.0345 (3)0.0361 (3)0.6958 (2)0.0198 (6)
C10A0.0667 (3)0.1068 (3)0.6088 (2)0.0222 (6)
H10A0.17050.11920.61130.027*
C11A0.0160 (3)0.1594 (3)0.5183 (2)0.0232 (6)
Br1A0.15542 (4)0.25729 (3)0.40004 (2)0.03233 (10)
C12A0.1353 (3)0.1454 (3)0.5130 (2)0.0246 (6)
H12A0.16870.18270.45070.029*
C13A0.2376 (3)0.0763 (3)0.5999 (2)0.0248 (6)
H13A0.34210.06640.59730.030*
C14A0.1883 (3)0.0214 (3)0.6905 (2)0.0212 (6)
O2A0.2832 (2)0.0477 (2)0.77902 (16)0.0265 (5)
N1B0.5589 (3)0.1904 (2)1.02282 (18)0.0235 (5)
C1B0.4498 (3)0.2837 (3)1.0340 (2)0.0215 (6)
C2B0.4523 (4)0.3566 (3)1.1007 (2)0.0272 (7)
H2B0.53200.34361.13810.033*
C3B0.3386 (4)0.4471 (3)1.1116 (2)0.0297 (7)
H3B0.33960.49491.15770.036*
C4B0.2227 (4)0.4691 (3)1.0563 (2)0.0306 (7)
H4B0.14780.53411.06200.037*
C5B0.2169 (3)0.3961 (3)0.9929 (2)0.0266 (7)
H5B0.13620.40950.95640.032*
C6B0.3289 (3)0.3025 (3)0.9820 (2)0.0209 (6)
C7B0.3173 (3)0.2169 (3)0.9224 (2)0.0224 (6)
O1B0.1980 (2)0.2107 (2)0.89065 (17)0.0307 (5)
N2B0.4387 (3)0.1394 (2)0.90652 (19)0.0224 (5)
C8B0.5894 (3)0.1544 (3)0.9271 (2)0.0217 (6)
H8B0.64270.07100.93960.026*
C9B0.6953 (3)0.2433 (3)0.8361 (2)0.0203 (6)
C10B0.6512 (3)0.3015 (3)0.7437 (2)0.0217 (6)
H10B0.54980.28940.73680.026*
C11B0.7546 (3)0.3770 (3)0.6619 (2)0.0246 (6)
Br1B0.69147 (4)0.45082 (3)0.53632 (2)0.03648 (11)
C12B0.9020 (4)0.3972 (3)0.6699 (2)0.0283 (7)
H12B0.97140.45010.61330.034*
C13B0.9479 (3)0.3395 (3)0.7613 (2)0.0258 (6)
H13B1.04940.35270.76750.031*
C14B0.8457 (3)0.2624 (3)0.8440 (2)0.0209 (6)
O2B0.8846 (2)0.2024 (2)0.93607 (16)0.0274 (5)
H1NA0.07470.19680.83340.040*
H1NB0.63660.18681.05810.040*
H2NA0.17090.08830.81990.040*
H2NB0.42850.08090.87500.040*
H2OA0.37700.05160.77510.040*
H2OB0.98130.21410.92790.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0159 (11)0.0269 (14)0.0256 (13)0.0034 (10)0.0037 (10)0.0049 (11)
C1A0.0204 (14)0.0291 (16)0.0183 (14)0.0018 (12)0.0080 (11)0.0041 (12)
C2A0.0309 (17)0.0272 (17)0.0253 (16)0.0028 (13)0.0102 (13)0.0054 (13)
C3A0.0415 (19)0.0265 (17)0.0278 (16)0.0022 (14)0.0123 (14)0.0098 (14)
C4A0.0276 (16)0.0382 (19)0.0293 (17)0.0080 (14)0.0100 (13)0.0163 (15)
C5A0.0224 (15)0.0331 (17)0.0255 (15)0.0019 (13)0.0102 (12)0.0094 (13)
C6A0.0190 (14)0.0276 (16)0.0203 (14)0.0012 (12)0.0084 (11)0.0049 (12)
C7A0.0182 (14)0.0290 (16)0.0192 (14)0.0000 (12)0.0076 (11)0.0052 (12)
O1A0.0148 (10)0.0353 (12)0.0316 (12)0.0002 (9)0.0082 (9)0.0126 (10)
N2A0.0144 (11)0.0293 (14)0.0281 (13)0.0006 (10)0.0059 (10)0.0130 (11)
C8A0.0134 (13)0.0323 (17)0.0236 (15)0.0002 (12)0.0037 (11)0.0115 (13)
C9A0.0163 (13)0.0207 (14)0.0250 (15)0.0014 (11)0.0053 (11)0.0105 (12)
C10A0.0150 (13)0.0240 (15)0.0288 (16)0.0027 (11)0.0044 (11)0.0093 (12)
C11A0.0210 (14)0.0206 (15)0.0265 (15)0.0008 (11)0.0047 (12)0.0048 (12)
Br1A0.02666 (17)0.03157 (19)0.03285 (18)0.00522 (13)0.00377 (13)0.00114 (14)
C12A0.0247 (15)0.0252 (16)0.0261 (15)0.0027 (12)0.0103 (12)0.0079 (13)
C13A0.0159 (14)0.0317 (17)0.0311 (16)0.0014 (12)0.0090 (12)0.0129 (13)
C14A0.0159 (13)0.0232 (15)0.0266 (15)0.0002 (11)0.0030 (11)0.0118 (12)
O2A0.0134 (10)0.0361 (12)0.0281 (11)0.0049 (9)0.0044 (8)0.0048 (9)
N1B0.0178 (12)0.0336 (14)0.0213 (12)0.0013 (10)0.0078 (10)0.0085 (11)
C1B0.0179 (14)0.0263 (15)0.0170 (13)0.0048 (11)0.0011 (11)0.0023 (12)
C2B0.0284 (16)0.0340 (18)0.0206 (15)0.0084 (13)0.0054 (12)0.0077 (13)
C3B0.0310 (17)0.0319 (18)0.0263 (16)0.0092 (14)0.0020 (13)0.0129 (14)
C4B0.0252 (16)0.0282 (17)0.0370 (18)0.0018 (13)0.0022 (14)0.0144 (14)
C5B0.0189 (14)0.0298 (17)0.0309 (17)0.0025 (12)0.0052 (12)0.0082 (13)
C6B0.0173 (13)0.0248 (15)0.0208 (14)0.0040 (11)0.0032 (11)0.0068 (12)
C7B0.0165 (13)0.0271 (16)0.0240 (15)0.0051 (11)0.0039 (11)0.0071 (12)
O1B0.0157 (10)0.0404 (13)0.0443 (13)0.0008 (9)0.0090 (9)0.0226 (11)
N2B0.0167 (12)0.0212 (13)0.0343 (14)0.0003 (10)0.0080 (10)0.0133 (11)
C8B0.0153 (13)0.0279 (16)0.0246 (15)0.0021 (11)0.0078 (11)0.0094 (12)
C9B0.0177 (13)0.0233 (15)0.0240 (15)0.0020 (11)0.0070 (11)0.0117 (12)
C10B0.0200 (14)0.0252 (15)0.0243 (15)0.0030 (12)0.0069 (12)0.0133 (12)
C11B0.0291 (16)0.0263 (16)0.0217 (15)0.0064 (13)0.0096 (12)0.0108 (13)
Br1B0.0462 (2)0.0396 (2)0.02454 (17)0.00589 (16)0.01352 (15)0.00780 (14)
C12B0.0254 (16)0.0275 (17)0.0284 (16)0.0011 (13)0.0008 (13)0.0080 (13)
C13B0.0167 (14)0.0287 (16)0.0337 (17)0.0006 (12)0.0054 (12)0.0119 (14)
C14B0.0186 (14)0.0220 (15)0.0247 (15)0.0044 (11)0.0069 (12)0.0104 (12)
O2B0.0153 (10)0.0376 (13)0.0288 (11)0.0000 (9)0.0095 (8)0.0049 (10)
Geometric parameters (Å, º) top
N1A—C1A1.384 (4)N1B—C1B1.379 (4)
N1A—C8A1.453 (4)N1B—C8B1.457 (4)
N1A—H1NA0.8822N1B—H1NB0.9273
C1A—C2A1.402 (4)C1B—C6B1.397 (4)
C1A—C6A1.405 (4)C1B—C2B1.408 (4)
C2A—C3A1.373 (4)C2B—C3B1.380 (4)
C2A—H2A0.9500C2B—H2B0.9500
C3A—C4A1.393 (5)C3B—C4B1.389 (5)
C3A—H3A0.9500C3B—H3B0.9500
C4A—C5A1.375 (4)C4B—C5B1.377 (4)
C4A—H4A0.9500C4B—H4B0.9500
C5A—C6A1.402 (4)C5B—C6B1.396 (4)
C5A—H5A0.9500C5B—H5B0.9500
C6A—C7A1.474 (4)C6B—C7B1.463 (4)
C7A—O1A1.242 (3)C7B—O1B1.252 (3)
C7A—N2A1.342 (4)C7B—N2B1.340 (4)
N2A—C8A1.459 (3)N2B—C8B1.461 (3)
N2A—H2NA0.9523N2B—H2NB0.9095
C8A—C9A1.528 (4)C8B—C9B1.522 (4)
C8A—H8A1.0000C8B—H8B1.0000
C9A—C10A1.388 (4)C9B—C10B1.390 (4)
C9A—C14A1.405 (4)C9B—C14B1.399 (4)
C10A—C11A1.387 (4)C10B—C11B1.382 (4)
C10A—H10A0.9500C10B—H10B0.9500
C11A—C12A1.381 (4)C11B—C12B1.377 (4)
C11A—Br1A1.903 (3)C11B—Br1B1.894 (3)
C12A—C13A1.386 (4)C12B—C13B1.385 (4)
C12A—H12A0.9500C12B—H12B0.9500
C13A—C14A1.386 (4)C13B—C14B1.391 (4)
C13A—H13A0.9500C13B—H13B0.9500
C14A—O2A1.368 (3)C14B—O2B1.370 (3)
O2A—H2OA0.8493O2B—H2OB0.8511
C1A—N1A—C8A116.9 (2)C1B—N1B—C8B117.7 (2)
C1A—N1A—H1NA115.4C1B—N1B—H1NB113.3
C8A—N1A—H1NA115.0C8B—N1B—H1NB121.5
N1A—C1A—C2A122.7 (3)N1B—C1B—C6B119.3 (3)
N1A—C1A—C6A118.9 (3)N1B—C1B—C2B121.6 (3)
C2A—C1A—C6A118.3 (3)C6B—C1B—C2B119.0 (3)
C3A—C2A—C1A120.2 (3)C3B—C2B—C1B119.8 (3)
C3A—C2A—H2A119.9C3B—C2B—H2B120.1
C1A—C2A—H2A119.9C1B—C2B—H2B120.1
C2A—C3A—C4A121.3 (3)C2B—C3B—C4B121.0 (3)
C2A—C3A—H3A119.3C2B—C3B—H3B119.5
C4A—C3A—H3A119.3C4B—C3B—H3B119.5
C5A—C4A—C3A119.4 (3)C5B—C4B—C3B119.6 (3)
C5A—C4A—H4A120.3C5B—C4B—H4B120.2
C3A—C4A—H4A120.3C3B—C4B—H4B120.2
C4A—C5A—C6A120.0 (3)C4B—C5B—C6B120.5 (3)
C4A—C5A—H5A120.0C4B—C5B—H5B119.8
C6A—C5A—H5A120.0C6B—C5B—H5B119.8
C5A—C6A—C1A120.5 (3)C5B—C6B—C1B120.1 (3)
C5A—C6A—C7A120.5 (3)C5B—C6B—C7B121.3 (3)
C1A—C6A—C7A118.7 (3)C1B—C6B—C7B118.5 (3)
O1A—C7A—N2A120.9 (3)O1B—C7B—N2B120.1 (3)
O1A—C7A—C6A123.0 (3)O1B—C7B—C6B122.8 (3)
N2A—C7A—C6A115.9 (2)N2B—C7B—C6B117.0 (2)
C7A—N2A—C8A122.3 (2)C7B—N2B—C8B122.6 (2)
C7A—N2A—H2NA114.5C7B—N2B—H2NB117.5
C8A—N2A—H2NA122.0C8B—N2B—H2NB119.5
N1A—C8A—N2A107.8 (2)N1B—C8B—N2B107.5 (2)
N1A—C8A—C9A113.3 (2)N1B—C8B—C9B113.8 (2)
N2A—C8A—C9A112.4 (2)N2B—C8B—C9B112.8 (2)
N1A—C8A—H8A107.7N1B—C8B—H8B107.5
N2A—C8A—H8A107.7N2B—C8B—H8B107.5
C9A—C8A—H8A107.7C9B—C8B—H8B107.5
C10A—C9A—C14A118.8 (3)C10B—C9B—C14B118.7 (3)
C10A—C9A—C8A124.0 (2)C10B—C9B—C8B122.6 (2)
C14A—C9A—C8A117.2 (2)C14B—C9B—C8B118.6 (2)
C11A—C10A—C9A119.9 (3)C11B—C10B—C9B120.2 (3)
C11A—C10A—H10A120.0C11B—C10B—H10B119.9
C9A—C10A—H10A120.0C9B—C10B—H10B119.9
C12A—C11A—C10A121.4 (3)C12B—C11B—C10B121.2 (3)
C12A—C11A—Br1A119.1 (2)C12B—C11B—Br1B120.0 (2)
C10A—C11A—Br1A119.4 (2)C10B—C11B—Br1B118.7 (2)
C11A—C12A—C13A119.1 (3)C11B—C12B—C13B119.3 (3)
C11A—C12A—H12A120.5C11B—C12B—H12B120.4
C13A—C12A—H12A120.5C13B—C12B—H12B120.4
C14A—C13A—C12A120.3 (3)C12B—C13B—C14B120.2 (3)
C14A—C13A—H13A119.8C12B—C13B—H13B119.9
C12A—C13A—H13A119.8C14B—C13B—H13B119.9
O2A—C14A—C13A123.3 (2)O2B—C14B—C13B122.9 (3)
O2A—C14A—C9A116.2 (3)O2B—C14B—C9B116.7 (3)
C13A—C14A—C9A120.5 (3)C13B—C14B—C9B120.4 (3)
C14A—O2A—H2OA114.4C14B—O2B—H2OB107.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2NA···O1B0.951.972.897 (3)165.2
N2B—H2NB···O1A0.912.052.914 (3)157.3
O2A—H2OA···O1Ai0.851.902.701 (3)156.7
O2B—H2OB···O1Bii0.851.862.691 (3)165.4
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC14H11BrN2O2
Mr319.16
Crystal system, space groupTriclinic, P1
Temperature (K)150
a, b, c (Å)8.8392 (5), 11.2252 (7), 13.8817 (8)
α, β, γ (°)73.0392 (9), 75.9620 (9), 85.0936 (9)
V3)1277.95 (13)
Z4
Radiation typeMo Kα
µ (mm1)3.22
Crystal size (mm)0.21 × 0.12 × 0.07
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.552, 0.806
No. of measured, independent and
observed [I > 2σ(I)] reflections
13015, 6129, 4580
Rint0.035
(sin θ/λ)max1)0.660
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.099, 1.03
No. of reflections6129
No. of parameters343
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.64, 0.71

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2NA···O1B0.951.972.897 (3)165.2
N2B—H2NB···O1A0.912.052.914 (3)157.3
O2A—H2OA···O1Ai0.851.902.701 (3)156.7
O2B—H2OB···O1Bii0.851.862.691 (3)165.4
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z.
 

Acknowledgements

We are grateful to the Research Council of Sharif University of Technology and Loughborough University for their financial support.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  CrossRef CAS Web of Science Google Scholar
First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationGoto, S., Tsuboi, H. & Kagara, K. (1993). Chem. Express, 8, 761–764.  CAS Google Scholar
First citationLiu, G. (2008). Acta Cryst. E64, o1677.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationMohri, S. J. (2001). Synth. Org. Chem. Jpn, 59, 514–515.  CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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