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

Boghaei, D.M.; Najafpour, M.M.; McKee, V.

doi:10.1107/S1600536808035678

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o193

doi:10.1107/S1600536808035678

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

Davar M. Boghaei,^a ^* Mohammad Mahdi Najafpour ^a and Vickie McKee ^b

^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 π–π 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 ); Goto et al. (1993 ); Mohri (2001 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₄H₁₁BrN₂O₂
M_r = 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 ) T_min = 0.552, T_max = 0.806
13015 measured reflections
6129 independent reflections
4580 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.099
S = 1.02
6129 reflections
343 parameters
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.70 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global, New_Global_Publ_Block. DOI: 10.1107/S1600536808035678/rz2254sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808035678/rz2254Isup2.hkl

checkCIF report

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 π–π 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.

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

	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.
	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

C₁₄H₁₁BrN₂O₂	Z = 4
M_r = 319.16	F(000) = 640
Triclinic, P1	D_x = 1.659 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8392 (5) Å	Cell parameters from 3058 reflections
b = 11.2252 (7) Å	θ = 2.4–25.8°
c = 13.8817 (8) Å	µ = 3.22 mm⁻¹
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 tube	4580 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 28.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −11→11
T_min = 0.552, T_max = 0.806	k = −14→14
13015 measured reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0415P)² + 0.6583P] where P = (F_o² + 2F_c²)/3
6129 reflections	(Δ/σ)_max = 0.001
343 parameters	Δρ_max = 0.64 e Å⁻³
0 restraints	Δρ_min = −0.71 e Å⁻³

Crystal data top

C₁₄H₁₁BrN₂O₂	γ = 85.0936 (9)°
M_r = 319.16	V = 1277.95 (13) Å³
Triclinic, P1	Z = 4
a = 8.8392 (5) Å	Mo Kα radiation
b = 11.2252 (7) Å	µ = 3.22 mm⁻¹
c = 13.8817 (8) Å	T = 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)
T_min = 0.552, T_max = 0.806	R_int = 0.035
13015 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.03	Δρ_max = 0.64 e Å⁻³
6129 reflections	Δρ_min = −0.71 e Å⁻³
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

	x	y	z	U_iso*/U_eq
N1A	0.0154 (3)	−0.1619 (2)	0.82388 (19)	0.0233 (5)
C1A	0.1438 (3)	−0.2154 (3)	0.7715 (2)	0.0226 (6)
C2A	0.1414 (4)	−0.3350 (3)	0.7594 (2)	0.0274 (7)
H2A	0.0487	−0.3822	0.7874	0.033*
C3A	0.2724 (4)	−0.3839 (3)	0.7072 (2)	0.0308 (7)
H3A	0.2693	−0.4652	0.7000	0.037*
C4A	0.4098 (4)	−0.3167 (3)	0.6646 (2)	0.0301 (7)
H4A	0.4981	−0.3506	0.6262	0.036*
C5A	0.4164 (3)	−0.2011 (3)	0.6785 (2)	0.0260 (7)
H5A	0.5103	−0.1554	0.6508	0.031*
C6A	0.2848 (3)	−0.1506 (3)	0.7335 (2)	0.0221 (6)
C7A	0.2963 (3)	−0.0355 (3)	0.7617 (2)	0.0219 (6)
O1A	0.4227 (2)	0.0103 (2)	0.75507 (16)	0.0260 (5)
N2A	0.1608 (3)	0.0141 (2)	0.80201 (19)	0.0227 (5)
C8A	0.0102 (3)	−0.0267 (3)	0.7988 (2)	0.0224 (6)
H8A	−0.0707	−0.0030	0.8545	0.027*
C9A	−0.0345 (3)	0.0361 (3)	0.6958 (2)	0.0198 (6)
C10A	0.0667 (3)	0.1068 (3)	0.6088 (2)	0.0222 (6)
H10A	0.1705	0.1192	0.6113	0.027*
C11A	0.0160 (3)	0.1594 (3)	0.5183 (2)	0.0232 (6)
Br1A	0.15542 (4)	0.25729 (3)	0.40004 (2)	0.03233 (10)
C12A	−0.1353 (3)	0.1454 (3)	0.5130 (2)	0.0246 (6)
H12A	−0.1687	0.1827	0.4507	0.029*
C13A	−0.2376 (3)	0.0763 (3)	0.5999 (2)	0.0248 (6)
H13A	−0.3421	0.0664	0.5973	0.030*
C14A	−0.1883 (3)	0.0214 (3)	0.6905 (2)	0.0212 (6)
O2A	−0.2832 (2)	−0.0477 (2)	0.77902 (16)	0.0265 (5)
N1B	0.5589 (3)	0.1904 (2)	1.02282 (18)	0.0235 (5)
C1B	0.4498 (3)	0.2837 (3)	1.0340 (2)	0.0215 (6)
C2B	0.4523 (4)	0.3566 (3)	1.1007 (2)	0.0272 (7)
H2B	0.5320	0.3436	1.1381	0.033*
C3B	0.3386 (4)	0.4471 (3)	1.1116 (2)	0.0297 (7)
H3B	0.3396	0.4949	1.1577	0.036*
C4B	0.2227 (4)	0.4691 (3)	1.0563 (2)	0.0306 (7)
H4B	0.1478	0.5341	1.0620	0.037*
C5B	0.2169 (3)	0.3961 (3)	0.9929 (2)	0.0266 (7)
H5B	0.1362	0.4095	0.9564	0.032*
C6B	0.3289 (3)	0.3025 (3)	0.9820 (2)	0.0209 (6)
C7B	0.3173 (3)	0.2169 (3)	0.9224 (2)	0.0224 (6)
O1B	0.1980 (2)	0.2107 (2)	0.89065 (17)	0.0307 (5)
N2B	0.4387 (3)	0.1394 (2)	0.90652 (19)	0.0224 (5)
C8B	0.5894 (3)	0.1544 (3)	0.9271 (2)	0.0217 (6)
H8B	0.6427	0.0710	0.9396	0.026*
C9B	0.6953 (3)	0.2433 (3)	0.8361 (2)	0.0203 (6)
C10B	0.6512 (3)	0.3015 (3)	0.7437 (2)	0.0217 (6)
H10B	0.5498	0.2894	0.7368	0.026*
C11B	0.7546 (3)	0.3770 (3)	0.6619 (2)	0.0246 (6)
Br1B	0.69147 (4)	0.45082 (3)	0.53632 (2)	0.03648 (11)
C12B	0.9020 (4)	0.3972 (3)	0.6699 (2)	0.0283 (7)
H12B	0.9714	0.4501	0.6133	0.034*
C13B	0.9479 (3)	0.3395 (3)	0.7613 (2)	0.0258 (6)
H13B	1.0494	0.3527	0.7675	0.031*
C14B	0.8457 (3)	0.2624 (3)	0.8440 (2)	0.0209 (6)
O2B	0.8846 (2)	0.2024 (2)	0.93607 (16)	0.0274 (5)
H1NA	−0.0747	−0.1968	0.8334	0.040*
H1NB	0.6366	0.1868	1.0581	0.040*
H2NA	0.1709	0.0883	0.8199	0.040*
H2NB	0.4285	0.0809	0.8750	0.040*
H2OA	−0.3770	−0.0516	0.7751	0.040*
H2OB	0.9813	0.2141	0.9279	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0159 (11)	0.0269 (14)	0.0256 (13)	−0.0034 (10)	−0.0037 (10)	−0.0049 (11)
C1A	0.0204 (14)	0.0291 (16)	0.0183 (14)	0.0018 (12)	−0.0080 (11)	−0.0041 (12)
C2A	0.0309 (17)	0.0272 (17)	0.0253 (16)	−0.0028 (13)	−0.0102 (13)	−0.0054 (13)
C3A	0.0415 (19)	0.0265 (17)	0.0278 (16)	0.0022 (14)	−0.0123 (14)	−0.0098 (14)
C4A	0.0276 (16)	0.0382 (19)	0.0293 (17)	0.0080 (14)	−0.0100 (13)	−0.0163 (15)
C5A	0.0224 (15)	0.0331 (17)	0.0255 (15)	0.0019 (13)	−0.0102 (12)	−0.0094 (13)
C6A	0.0190 (14)	0.0276 (16)	0.0203 (14)	0.0012 (12)	−0.0084 (11)	−0.0049 (12)
C7A	0.0182 (14)	0.0290 (16)	0.0192 (14)	0.0000 (12)	−0.0076 (11)	−0.0052 (12)
O1A	0.0148 (10)	0.0353 (12)	0.0316 (12)	−0.0002 (9)	−0.0082 (9)	−0.0126 (10)
N2A	0.0144 (11)	0.0293 (14)	0.0281 (13)	−0.0006 (10)	−0.0059 (10)	−0.0130 (11)
C8A	0.0134 (13)	0.0323 (17)	0.0236 (15)	−0.0002 (12)	−0.0037 (11)	−0.0115 (13)
C9A	0.0163 (13)	0.0207 (14)	0.0250 (15)	0.0014 (11)	−0.0053 (11)	−0.0105 (12)
C10A	0.0150 (13)	0.0240 (15)	0.0288 (16)	−0.0027 (11)	−0.0044 (11)	−0.0093 (12)
C11A	0.0210 (14)	0.0206 (15)	0.0265 (15)	−0.0008 (11)	−0.0047 (12)	−0.0048 (12)
Br1A	0.02666 (17)	0.03157 (19)	0.03285 (18)	−0.00522 (13)	−0.00377 (13)	−0.00114 (14)
C12A	0.0247 (15)	0.0252 (16)	0.0261 (15)	0.0027 (12)	−0.0103 (12)	−0.0079 (13)
C13A	0.0159 (14)	0.0317 (17)	0.0311 (16)	0.0014 (12)	−0.0090 (12)	−0.0129 (13)
C14A	0.0159 (13)	0.0232 (15)	0.0266 (15)	−0.0002 (11)	−0.0030 (11)	−0.0118 (12)
O2A	0.0134 (10)	0.0361 (12)	0.0281 (11)	−0.0049 (9)	−0.0044 (8)	−0.0048 (9)
N1B	0.0178 (12)	0.0336 (14)	0.0213 (12)	0.0013 (10)	−0.0078 (10)	−0.0085 (11)
C1B	0.0179 (14)	0.0263 (15)	0.0170 (13)	−0.0048 (11)	−0.0011 (11)	−0.0023 (12)
C2B	0.0284 (16)	0.0340 (18)	0.0206 (15)	−0.0084 (13)	−0.0054 (12)	−0.0077 (13)
C3B	0.0310 (17)	0.0319 (18)	0.0263 (16)	−0.0092 (14)	0.0020 (13)	−0.0129 (14)
C4B	0.0252 (16)	0.0282 (17)	0.0370 (18)	−0.0018 (13)	0.0022 (14)	−0.0144 (14)
C5B	0.0189 (14)	0.0298 (17)	0.0309 (17)	−0.0025 (12)	−0.0052 (12)	−0.0082 (13)
C6B	0.0173 (13)	0.0248 (15)	0.0208 (14)	−0.0040 (11)	−0.0032 (11)	−0.0068 (12)
C7B	0.0165 (13)	0.0271 (16)	0.0240 (15)	−0.0051 (11)	−0.0039 (11)	−0.0071 (12)
O1B	0.0157 (10)	0.0404 (13)	0.0443 (13)	−0.0008 (9)	−0.0090 (9)	−0.0226 (11)
N2B	0.0167 (12)	0.0212 (13)	0.0343 (14)	−0.0003 (10)	−0.0080 (10)	−0.0133 (11)
C8B	0.0153 (13)	0.0279 (16)	0.0246 (15)	0.0021 (11)	−0.0078 (11)	−0.0094 (12)
C9B	0.0177 (13)	0.0233 (15)	0.0240 (15)	0.0020 (11)	−0.0070 (11)	−0.0117 (12)
C10B	0.0200 (14)	0.0252 (15)	0.0243 (15)	0.0030 (12)	−0.0069 (12)	−0.0133 (12)
C11B	0.0291 (16)	0.0263 (16)	0.0217 (15)	0.0064 (13)	−0.0096 (12)	−0.0108 (13)
Br1B	0.0462 (2)	0.0396 (2)	0.02454 (17)	0.00589 (16)	−0.01352 (15)	−0.00780 (14)
C12B	0.0254 (16)	0.0275 (17)	0.0284 (16)	−0.0011 (13)	0.0008 (13)	−0.0080 (13)
C13B	0.0167 (14)	0.0287 (16)	0.0337 (17)	0.0006 (12)	−0.0054 (12)	−0.0119 (14)
C14B	0.0186 (14)	0.0220 (15)	0.0247 (15)	0.0044 (11)	−0.0069 (12)	−0.0104 (12)
O2B	0.0153 (10)	0.0376 (13)	0.0288 (11)	0.0000 (9)	−0.0095 (8)	−0.0049 (10)

Geometric parameters (Å, º) top

N1A—C1A	1.384 (4)	N1B—C1B	1.379 (4)
N1A—C8A	1.453 (4)	N1B—C8B	1.457 (4)
N1A—H1NA	0.8822	N1B—H1NB	0.9273
C1A—C2A	1.402 (4)	C1B—C6B	1.397 (4)
C1A—C6A	1.405 (4)	C1B—C2B	1.408 (4)
C2A—C3A	1.373 (4)	C2B—C3B	1.380 (4)
C2A—H2A	0.9500	C2B—H2B	0.9500
C3A—C4A	1.393 (5)	C3B—C4B	1.389 (5)
C3A—H3A	0.9500	C3B—H3B	0.9500
C4A—C5A	1.375 (4)	C4B—C5B	1.377 (4)
C4A—H4A	0.9500	C4B—H4B	0.9500
C5A—C6A	1.402 (4)	C5B—C6B	1.396 (4)
C5A—H5A	0.9500	C5B—H5B	0.9500
C6A—C7A	1.474 (4)	C6B—C7B	1.463 (4)
C7A—O1A	1.242 (3)	C7B—O1B	1.252 (3)
C7A—N2A	1.342 (4)	C7B—N2B	1.340 (4)
N2A—C8A	1.459 (3)	N2B—C8B	1.461 (3)
N2A—H2NA	0.9523	N2B—H2NB	0.9095
C8A—C9A	1.528 (4)	C8B—C9B	1.522 (4)
C8A—H8A	1.0000	C8B—H8B	1.0000
C9A—C10A	1.388 (4)	C9B—C10B	1.390 (4)
C9A—C14A	1.405 (4)	C9B—C14B	1.399 (4)
C10A—C11A	1.387 (4)	C10B—C11B	1.382 (4)
C10A—H10A	0.9500	C10B—H10B	0.9500
C11A—C12A	1.381 (4)	C11B—C12B	1.377 (4)
C11A—Br1A	1.903 (3)	C11B—Br1B	1.894 (3)
C12A—C13A	1.386 (4)	C12B—C13B	1.385 (4)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—C14A	1.386 (4)	C13B—C14B	1.391 (4)
C13A—H13A	0.9500	C13B—H13B	0.9500
C14A—O2A	1.368 (3)	C14B—O2B	1.370 (3)
O2A—H2OA	0.8493	O2B—H2OB	0.8511

C1A—N1A—C8A	116.9 (2)	C1B—N1B—C8B	117.7 (2)
C1A—N1A—H1NA	115.4	C1B—N1B—H1NB	113.3
C8A—N1A—H1NA	115.0	C8B—N1B—H1NB	121.5
N1A—C1A—C2A	122.7 (3)	N1B—C1B—C6B	119.3 (3)
N1A—C1A—C6A	118.9 (3)	N1B—C1B—C2B	121.6 (3)
C2A—C1A—C6A	118.3 (3)	C6B—C1B—C2B	119.0 (3)
C3A—C2A—C1A	120.2 (3)	C3B—C2B—C1B	119.8 (3)
C3A—C2A—H2A	119.9	C3B—C2B—H2B	120.1
C1A—C2A—H2A	119.9	C1B—C2B—H2B	120.1
C2A—C3A—C4A	121.3 (3)	C2B—C3B—C4B	121.0 (3)
C2A—C3A—H3A	119.3	C2B—C3B—H3B	119.5
C4A—C3A—H3A	119.3	C4B—C3B—H3B	119.5
C5A—C4A—C3A	119.4 (3)	C5B—C4B—C3B	119.6 (3)
C5A—C4A—H4A	120.3	C5B—C4B—H4B	120.2
C3A—C4A—H4A	120.3	C3B—C4B—H4B	120.2
C4A—C5A—C6A	120.0 (3)	C4B—C5B—C6B	120.5 (3)
C4A—C5A—H5A	120.0	C4B—C5B—H5B	119.8
C6A—C5A—H5A	120.0	C6B—C5B—H5B	119.8
C5A—C6A—C1A	120.5 (3)	C5B—C6B—C1B	120.1 (3)
C5A—C6A—C7A	120.5 (3)	C5B—C6B—C7B	121.3 (3)
C1A—C6A—C7A	118.7 (3)	C1B—C6B—C7B	118.5 (3)
O1A—C7A—N2A	120.9 (3)	O1B—C7B—N2B	120.1 (3)
O1A—C7A—C6A	123.0 (3)	O1B—C7B—C6B	122.8 (3)
N2A—C7A—C6A	115.9 (2)	N2B—C7B—C6B	117.0 (2)
C7A—N2A—C8A	122.3 (2)	C7B—N2B—C8B	122.6 (2)
C7A—N2A—H2NA	114.5	C7B—N2B—H2NB	117.5
C8A—N2A—H2NA	122.0	C8B—N2B—H2NB	119.5
N1A—C8A—N2A	107.8 (2)	N1B—C8B—N2B	107.5 (2)
N1A—C8A—C9A	113.3 (2)	N1B—C8B—C9B	113.8 (2)
N2A—C8A—C9A	112.4 (2)	N2B—C8B—C9B	112.8 (2)
N1A—C8A—H8A	107.7	N1B—C8B—H8B	107.5
N2A—C8A—H8A	107.7	N2B—C8B—H8B	107.5
C9A—C8A—H8A	107.7	C9B—C8B—H8B	107.5
C10A—C9A—C14A	118.8 (3)	C10B—C9B—C14B	118.7 (3)
C10A—C9A—C8A	124.0 (2)	C10B—C9B—C8B	122.6 (2)
C14A—C9A—C8A	117.2 (2)	C14B—C9B—C8B	118.6 (2)
C11A—C10A—C9A	119.9 (3)	C11B—C10B—C9B	120.2 (3)
C11A—C10A—H10A	120.0	C11B—C10B—H10B	119.9
C9A—C10A—H10A	120.0	C9B—C10B—H10B	119.9
C12A—C11A—C10A	121.4 (3)	C12B—C11B—C10B	121.2 (3)
C12A—C11A—Br1A	119.1 (2)	C12B—C11B—Br1B	120.0 (2)
C10A—C11A—Br1A	119.4 (2)	C10B—C11B—Br1B	118.7 (2)
C11A—C12A—C13A	119.1 (3)	C11B—C12B—C13B	119.3 (3)
C11A—C12A—H12A	120.5	C11B—C12B—H12B	120.4
C13A—C12A—H12A	120.5	C13B—C12B—H12B	120.4
C14A—C13A—C12A	120.3 (3)	C12B—C13B—C14B	120.2 (3)
C14A—C13A—H13A	119.8	C12B—C13B—H13B	119.9
C12A—C13A—H13A	119.8	C14B—C13B—H13B	119.9
O2A—C14A—C13A	123.3 (2)	O2B—C14B—C13B	122.9 (3)
O2A—C14A—C9A	116.2 (3)	O2B—C14B—C9B	116.7 (3)
C13A—C14A—C9A	120.5 (3)	C13B—C14B—C9B	120.4 (3)
C14A—O2A—H2OA	114.4	C14B—O2B—H2OB	107.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2NA···O1B	0.95	1.97	2.897 (3)	165.2
N2B—H2NB···O1A	0.91	2.05	2.914 (3)	157.3
O2A—H2OA···O1Aⁱ	0.85	1.90	2.701 (3)	156.7
O2B—H2OB···O1Bⁱⁱ	0.85	1.86	2.691 (3)	165.4

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁BrN₂O₂
M_r	319.16
Crystal system, space group	Triclinic, 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)
V (Å³)	1277.95 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.22
Crystal size (mm)	0.21 × 0.12 × 0.07

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.552, 0.806
No. of measured, independent and observed [I > 2σ(I)] reflections	13015, 6129, 4580
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.099, 1.03
No. of reflections	6129
No. of parameters	343
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
N2A—H2NA···O1B	0.95	1.97	2.897 (3)	165.2
N2B—H2NB···O1A	0.91	2.05	2.914 (3)	157.3
O2A—H2OA···O1Aⁱ	0.85	1.90	2.701 (3)	156.7
O2B—H2OB···O1Bⁱⁱ	0.85	1.86	2.691 (3)	165.4

Symmetry codes: (i) x−1, 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

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