Ethyl 2-(4-bromo­phen­yl)-1-phenyl-1H-benzimidazole-5-carboxyl­ate

Yoon, Y.K.; Ali, M.A.; Choon, T.S.; Arshad, S.; Razak, I.A.

doi:10.1107/S1600536812019897

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1683

doi:10.1107/S1600536812019897

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Ethyl 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole-5-carboxylate

Yeong Keng Yoon,^a Mohamed Ashraf Ali,^a Tan Soo Choon,^a Suhana Arshad ^b and Ibrahim Abdul Razak ^b ^*‡

^aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia, and ^bSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: arazaki@usm.my

(Received 24 April 2012; accepted 3 May 2012; online 12 May 2012)

In the title compound, C₂₂H₁₇BrN₂O₂, the benzimidazole ring system is essentially planar, with a maximum deviation of 0.017 (1) Å, and forms dihedral angles of 27.79 (6) and 64.43 (6)° with the phenyl and bromo-substituted benzene rings, respectively. In the crystal, molecules are linked into one-dimensional chains along the a axis by weak C—H⋯O hydrogen bonds. Weak intermolecular C—H⋯π interactions are also present.

Related literature

For background to and the biological activities of benzimidazoles, see: Townsend & Revankar (1970 ); Rao et al. (2002 ); Thakurdesai et al. (2007 ); Dubey & Sanyal (2010 ); Lacey (1990 ). For a related structure, see: Arumugam et al. (2010 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₂H₁₇BrN₂O₂
M_r = 421.29
Triclinic, $[P \overline 1]$
a = 9.3121 (2) Å
b = 9.8136 (2) Å
c = 11.8458 (2) Å
α = 108.217 (1)°
β = 101.135 (1)°
γ = 109.361 (1)°
V = 915.39 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.27 mm⁻¹
T = 100 K
0.42 × 0.33 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.450, T_max = 0.728
21718 measured reflections
5326 independent reflections
4846 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.071
S = 1.06
5326 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1/N1/C1/C6/C7 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O2ⁱ	0.95	2.38	3.311 (2)	166
C19—H19A⋯Cg2ⁱⁱ	0.95	2.59	3.4534 (18)	152
C21—H21A⋯Cg1ⁱⁱⁱ	0.99	2.64	3.5288 (15)	149
Symmetry codes: (i) x-1, y, z; (ii) -x, -y, -z; (iii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812019897/lh5466sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019897/lh5466Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812019897/lh5466Isup3.cml

checkCIF report

Comment top

Benzimidazoles are a class of bioactive heterocyclic compounds which exhibit a wide range of activities such as anti-cancer (Townsend & Revankar, 1970), anti-HIV (Rao et al., 2002), anti-inflammatory (Thakurdesai et al., 2007) and anthelmintics (Dubey & Sanyal, 2010). The primary mechanism of action of benzimidazoles as anthelmintics is by binding to free β-tubulin and inhibiting its polymerization (Lacey, 1990). A number of benzimidazoles have been shown to also inhibit mammalian tubulin polymerization and to be aneugenic in vivo.

The molecular structure is shown in Fig. 1. Bond lengths and angles are within normal ranges and are comparable to a related structure (Arumugam et al.,2010). The benzimidazole ring system (N1/N2/C1—C7) is essentially planar with a maximum deviation of 0.017 (1) Å for atom C7. The dihedral angles of the benzimidazole ring (N1/N2/C1—C7) with the phenyl ring (C14–C19) and the bromo-substituted benzene ring (C8–C13) are 27.79 (6) and 64.43 (6)°, respectively.

In the crystal packing (Fig. 2), intermolecular C15—H15A···O2ⁱ (Table 1) hydrogen bonds link the molecules into one-dimensional zigzag chains along the a-axis. In addition, the crystal structure is further stabilized by the intermolecular C21—H21A···Cg1ⁱⁱⁱ and C19—H19A···Cg2ⁱⁱ (Table 1) interactions (Cg1 and Cg2 are the centroids of N1/N1/C1/C6/C7 and C8–C13 rings, respectively).

Related literature top

For background to and the biological activities of benzimidazoles, see: Townsend & Revankar (1970); Rao et al. (2002); Thakurdesai et al. (2007); Dubey & Sanyal (2010); Lacey (1990). For a related structure, see: Arumugam et al. (2010). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

Ethyl 3-amino-4-(phenyl amino) benzoate (0.84 mmol) and sodium metabisulfite adduct of bromo benzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was reflux at 403K for 2 h. After completion, the reaction mixture was diluted in ethyl acetate (20 ml) and washed with water (20 ml). The organic layer was collected, dried over Na₂SO₄ and the evaporated in vacuo to yield the product. The product was recrystallized from ethyl acetate.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

Ethyl 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole-5-carboxylate top

Crystal data top

C₂₂H₁₇BrN₂O₂	Z = 2
M_r = 421.29	F(000) = 428
Triclinic, P1	D_x = 1.528 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3121 (2) Å	Cell parameters from 9874 reflections
b = 9.8136 (2) Å	θ = 2.4–32.7°
c = 11.8458 (2) Å	µ = 2.27 mm⁻¹
α = 108.217 (1)°	T = 100 K
β = 101.135 (1)°	Block, colourless
γ = 109.361 (1)°	0.42 × 0.33 × 0.15 mm
V = 915.39 (3) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5326 independent reflections
Radiation source: fine-focus sealed tube	4846 reflections with I > I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 30.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
T_min = 0.450, T_max = 0.728	k = −13→13
21718 measured reflections	l = −16→16

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.071	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0366P)² + 0.3723P] where P = (F_o² + 2F_c²)/3
5326 reflections	(Δ/σ)_max = 0.001
245 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

C₂₂H₁₇BrN₂O₂	γ = 109.361 (1)°
M_r = 421.29	V = 915.39 (3) Å³
Triclinic, P1	Z = 2
a = 9.3121 (2) Å	Mo Kα radiation
b = 9.8136 (2) Å	µ = 2.27 mm⁻¹
c = 11.8458 (2) Å	T = 100 K
α = 108.217 (1)°	0.42 × 0.33 × 0.15 mm
β = 101.135 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5326 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4846 reflections with I > I > 2σ(I)
T_min = 0.450, T_max = 0.728	R_int = 0.025
21718 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.071	H-atom parameters constrained
S = 1.06	Δρ_max = 0.53 e Å⁻³
5326 reflections	Δρ_min = −0.65 e Å⁻³
245 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 100.0 (1) K.

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
Br1	−0.680059 (17)	−0.321236 (17)	−0.071893 (14)	0.02360 (5)
O1	0.66395 (12)	−0.10601 (12)	0.40079 (10)	0.0201 (2)
O2	0.84619 (13)	0.14498 (13)	0.46778 (10)	0.0230 (2)
N1	0.12223 (14)	−0.10878 (14)	0.20976 (11)	0.0180 (2)
N2	0.16438 (14)	0.14058 (14)	0.23396 (11)	0.0163 (2)
C1	0.31426 (17)	0.14481 (16)	0.28300 (13)	0.0167 (2)
C2	0.46861 (18)	0.26876 (17)	0.34068 (14)	0.0202 (3)
H2A	0.4867	0.3736	0.3505	0.024*
C3	0.59380 (18)	0.23123 (17)	0.38280 (14)	0.0205 (3)
H3A	0.7005	0.3123	0.4226	0.025*
C4	0.56651 (17)	0.07511 (17)	0.36785 (13)	0.0181 (3)
C5	0.41259 (17)	−0.04732 (17)	0.30997 (13)	0.0184 (3)
H5A	0.3946	−0.1522	0.2997	0.022*
C6	0.28543 (17)	−0.01088 (16)	0.26745 (13)	0.0168 (2)
C7	0.05354 (17)	−0.01604 (16)	0.19171 (12)	0.0160 (2)
C8	−0.12145 (16)	−0.07748 (16)	0.13144 (12)	0.0164 (2)
C9	−0.21833 (17)	−0.21394 (17)	0.14191 (13)	0.0182 (3)
H9A	−0.1695	−0.2591	0.1889	0.022*
C10	−0.38444 (17)	−0.28386 (17)	0.08468 (13)	0.0192 (3)
H10A	−0.4497	−0.3741	0.0945	0.023*
C11	−0.45403 (17)	−0.21985 (17)	0.01266 (13)	0.0183 (3)
C12	−0.36095 (17)	−0.08657 (17)	−0.00143 (13)	0.0183 (3)
H12A	−0.4102	−0.0453	−0.0520	0.022*
C13	−0.19447 (17)	−0.01399 (16)	0.05949 (13)	0.0172 (2)
H13A	−0.1303	0.0788	0.0522	0.021*
C14	0.13582 (17)	0.27765 (16)	0.24107 (13)	0.0168 (2)
C15	0.04564 (17)	0.32281 (17)	0.31392 (13)	0.0187 (3)
H15A	0.0000	0.2619	0.3569	0.022*
C16	0.02336 (18)	0.45862 (18)	0.32284 (14)	0.0220 (3)
H16A	−0.0369	0.4914	0.3732	0.026*
C17	0.08845 (19)	0.54698 (18)	0.25870 (15)	0.0236 (3)
H17A	0.0729	0.6397	0.2654	0.028*
C18	0.1760 (2)	0.49909 (18)	0.18500 (15)	0.0250 (3)
H18A	0.2188	0.5582	0.1400	0.030*
C19	0.20176 (19)	0.36444 (17)	0.17651 (14)	0.0208 (3)
H19A	0.2635	0.3326	0.1273	0.025*
C20	0.70792 (17)	0.04581 (17)	0.41792 (13)	0.0183 (3)
C21	0.79333 (17)	−0.14750 (17)	0.44476 (13)	0.0199 (3)
H21A	0.8430	−0.0922	0.5375	0.024*
H21B	0.8778	−0.1179	0.4063	0.024*
C22	0.7174 (2)	−0.32313 (19)	0.40531 (15)	0.0264 (3)
H22A	0.8004	−0.3580	0.4316	0.040*
H22B	0.6670	−0.3758	0.3135	0.040*
H22C	0.6353	−0.3502	0.4451	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01607 (8)	0.02227 (8)	0.02755 (8)	0.00650 (6)	0.00244 (6)	0.00860 (6)
O1	0.0153 (5)	0.0192 (5)	0.0243 (5)	0.0073 (4)	0.0042 (4)	0.0083 (4)
O2	0.0168 (5)	0.0232 (5)	0.0259 (5)	0.0062 (4)	0.0054 (4)	0.0095 (4)
N1	0.0162 (5)	0.0167 (5)	0.0189 (5)	0.0060 (4)	0.0031 (4)	0.0071 (5)
N2	0.0162 (5)	0.0144 (5)	0.0182 (5)	0.0060 (4)	0.0053 (4)	0.0071 (4)
C1	0.0171 (6)	0.0170 (6)	0.0176 (6)	0.0076 (5)	0.0063 (5)	0.0082 (5)
C2	0.0196 (7)	0.0163 (6)	0.0232 (7)	0.0057 (5)	0.0067 (5)	0.0083 (5)
C3	0.0167 (6)	0.0182 (6)	0.0235 (7)	0.0042 (5)	0.0061 (5)	0.0082 (5)
C4	0.0167 (6)	0.0190 (6)	0.0182 (6)	0.0073 (5)	0.0059 (5)	0.0075 (5)
C5	0.0183 (6)	0.0171 (6)	0.0193 (6)	0.0071 (5)	0.0059 (5)	0.0073 (5)
C6	0.0166 (6)	0.0155 (6)	0.0160 (6)	0.0052 (5)	0.0042 (5)	0.0060 (5)
C7	0.0173 (6)	0.0148 (6)	0.0147 (6)	0.0057 (5)	0.0047 (5)	0.0061 (5)
C8	0.0158 (6)	0.0168 (6)	0.0141 (6)	0.0063 (5)	0.0039 (5)	0.0046 (5)
C9	0.0195 (6)	0.0185 (6)	0.0158 (6)	0.0077 (5)	0.0044 (5)	0.0071 (5)
C10	0.0191 (6)	0.0179 (6)	0.0175 (6)	0.0053 (5)	0.0052 (5)	0.0063 (5)
C11	0.0164 (6)	0.0193 (6)	0.0170 (6)	0.0077 (5)	0.0049 (5)	0.0049 (5)
C12	0.0207 (7)	0.0188 (6)	0.0166 (6)	0.0111 (5)	0.0053 (5)	0.0062 (5)
C13	0.0188 (6)	0.0164 (6)	0.0166 (6)	0.0077 (5)	0.0064 (5)	0.0064 (5)
C14	0.0171 (6)	0.0151 (6)	0.0163 (6)	0.0061 (5)	0.0035 (5)	0.0058 (5)
C15	0.0176 (6)	0.0197 (6)	0.0184 (6)	0.0075 (5)	0.0055 (5)	0.0079 (5)
C16	0.0202 (7)	0.0218 (7)	0.0230 (7)	0.0107 (6)	0.0062 (5)	0.0064 (6)
C17	0.0234 (7)	0.0170 (6)	0.0267 (7)	0.0084 (6)	0.0027 (6)	0.0076 (6)
C18	0.0322 (8)	0.0193 (7)	0.0236 (7)	0.0087 (6)	0.0086 (6)	0.0117 (6)
C19	0.0262 (7)	0.0179 (6)	0.0190 (6)	0.0087 (6)	0.0100 (6)	0.0075 (5)
C20	0.0183 (6)	0.0200 (6)	0.0172 (6)	0.0080 (5)	0.0074 (5)	0.0076 (5)
C21	0.0178 (6)	0.0230 (7)	0.0187 (6)	0.0105 (6)	0.0043 (5)	0.0075 (5)
C22	0.0304 (8)	0.0243 (7)	0.0254 (7)	0.0135 (6)	0.0076 (6)	0.0100 (6)

Geometric parameters (Å, º) top

Br1—C11	1.8967 (14)	C10—C11	1.391 (2)
O1—C20	1.3428 (17)	C10—H10A	0.9500
O1—C21	1.4506 (17)	C11—C12	1.390 (2)
O2—C20	1.2124 (18)	C12—C13	1.3949 (19)
N1—C7	1.3182 (17)	C12—H12A	0.9500
N1—C6	1.3856 (18)	C13—H13A	0.9500
N2—C1	1.3858 (17)	C14—C19	1.3889 (19)
N2—C7	1.3950 (17)	C14—C15	1.3906 (19)
N2—C14	1.4360 (17)	C15—C16	1.391 (2)
C1—C2	1.398 (2)	C15—H15A	0.9500
C1—C6	1.4047 (19)	C16—C17	1.392 (2)
C2—C3	1.385 (2)	C16—H16A	0.9500
C2—H2A	0.9500	C17—C18	1.386 (2)
C3—C4	1.414 (2)	C17—H17A	0.9500
C3—H3A	0.9500	C18—C19	1.396 (2)
C4—C5	1.3898 (19)	C18—H18A	0.9500
C4—C20	1.4915 (19)	C19—H19A	0.9500
C5—C6	1.3953 (19)	C21—C22	1.500 (2)
C5—H5A	0.9500	C21—H21A	0.9900
C7—C8	1.4692 (19)	C21—H21B	0.9900
C8—C13	1.4022 (19)	C22—H22A	0.9800
C8—C9	1.4031 (19)	C22—H22B	0.9800
C9—C10	1.387 (2)	C22—H22C	0.9800
C9—H9A	0.9500

C20—O1—C21	115.96 (11)	C11—C12—H12A	120.3
C7—N1—C6	105.29 (11)	C13—C12—H12A	120.3
C1—N2—C7	106.01 (11)	C12—C13—C8	120.27 (13)
C1—N2—C14	124.37 (11)	C12—C13—H13A	119.9
C7—N2—C14	129.28 (12)	C8—C13—H13A	119.9
N2—C1—C2	131.97 (13)	C19—C14—C15	121.23 (13)
N2—C1—C6	105.65 (12)	C19—C14—N2	119.07 (12)
C2—C1—C6	122.36 (13)	C15—C14—N2	119.69 (12)
C3—C2—C1	116.72 (13)	C14—C15—C16	118.92 (13)
C3—C2—H2A	121.6	C14—C15—H15A	120.5
C1—C2—H2A	121.6	C16—C15—H15A	120.5
C2—C3—C4	121.52 (13)	C15—C16—C17	120.63 (14)
C2—C3—H3A	119.2	C15—C16—H16A	119.7
C4—C3—H3A	119.2	C17—C16—H16A	119.7
C5—C4—C3	121.27 (13)	C18—C17—C16	119.74 (14)
C5—C4—C20	120.79 (13)	C18—C17—H17A	120.1
C3—C4—C20	117.94 (13)	C16—C17—H17A	120.1
C4—C5—C6	117.74 (13)	C17—C18—C19	120.41 (14)
C4—C5—H5A	121.1	C17—C18—H18A	119.8
C6—C5—H5A	121.1	C19—C18—H18A	119.8
N1—C6—C5	129.29 (13)	C14—C19—C18	119.06 (13)
N1—C6—C1	110.30 (12)	C14—C19—H19A	120.5
C5—C6—C1	120.40 (13)	C18—C19—H19A	120.5
N1—C7—N2	112.74 (12)	O2—C20—O1	123.35 (13)
N1—C7—C8	121.69 (12)	O2—C20—C4	125.07 (13)
N2—C7—C8	125.56 (12)	O1—C20—C4	111.58 (12)
C13—C8—C9	119.05 (13)	O1—C21—C22	106.03 (12)
C13—C8—C7	124.21 (12)	O1—C21—H21A	110.5
C9—C8—C7	116.64 (12)	C22—C21—H21A	110.5
C10—C9—C8	120.93 (13)	O1—C21—H21B	110.5
C10—C9—H9A	119.5	C22—C21—H21B	110.5
C8—C9—H9A	119.5	H21A—C21—H21B	108.7
C9—C10—C11	119.00 (13)	C21—C22—H22A	109.5
C9—C10—H10A	120.5	C21—C22—H22B	109.5
C11—C10—H10A	120.5	H22A—C22—H22B	109.5
C12—C11—C10	121.39 (13)	C21—C22—H22C	109.5
C12—C11—Br1	119.62 (11)	H22A—C22—H22C	109.5
C10—C11—Br1	118.97 (11)	H22B—C22—H22C	109.5
C11—C12—C13	119.32 (13)

C7—N2—C1—C2	−178.43 (15)	C13—C8—C9—C10	−1.5 (2)
C14—N2—C1—C2	−4.5 (2)	C7—C8—C9—C10	−177.86 (12)
C7—N2—C1—C6	0.05 (14)	C8—C9—C10—C11	2.2 (2)
C14—N2—C1—C6	173.96 (12)	C9—C10—C11—C12	−0.9 (2)
N2—C1—C2—C3	178.10 (14)	C9—C10—C11—Br1	177.12 (10)
C6—C1—C2—C3	−0.2 (2)	C10—C11—C12—C13	−1.0 (2)
C1—C2—C3—C4	0.1 (2)	Br1—C11—C12—C13	−179.04 (10)
C2—C3—C4—C5	0.1 (2)	C11—C12—C13—C8	1.7 (2)
C2—C3—C4—C20	−179.00 (13)	C9—C8—C13—C12	−0.5 (2)
C3—C4—C5—C6	−0.3 (2)	C7—C8—C13—C12	175.61 (13)
C20—C4—C5—C6	178.81 (12)	C1—N2—C14—C19	65.95 (18)
C7—N1—C6—C5	178.30 (14)	C7—N2—C14—C19	−121.62 (16)
C7—N1—C6—C1	−0.54 (15)	C1—N2—C14—C15	−112.87 (15)
C4—C5—C6—N1	−178.52 (13)	C7—N2—C14—C15	59.56 (19)
C4—C5—C6—C1	0.2 (2)	C19—C14—C15—C16	−0.8 (2)
N2—C1—C6—N1	0.30 (15)	N2—C14—C15—C16	178.04 (13)
C2—C1—C6—N1	178.95 (13)	C14—C15—C16—C17	0.8 (2)
N2—C1—C6—C5	−178.66 (12)	C15—C16—C17—C18	0.1 (2)
C2—C1—C6—C5	0.0 (2)	C16—C17—C18—C19	−1.1 (2)
C6—N1—C7—N2	0.58 (15)	C15—C14—C19—C18	−0.2 (2)
C6—N1—C7—C8	179.77 (12)	N2—C14—C19—C18	−179.03 (13)
C1—N2—C7—N1	−0.40 (15)	C17—C18—C19—C14	1.2 (2)
C14—N2—C7—N1	−173.91 (13)	C21—O1—C20—O2	−0.62 (19)
C1—N2—C7—C8	−179.56 (12)	C21—O1—C20—C4	179.17 (11)
C14—N2—C7—C8	6.9 (2)	C5—C4—C20—O2	178.78 (14)
N1—C7—C8—C13	−149.98 (14)	C3—C4—C20—O2	−2.1 (2)
N2—C7—C8—C13	29.1 (2)	C5—C4—C20—O1	−1.01 (18)
N1—C7—C8—C9	26.20 (19)	C3—C4—C20—O1	178.09 (12)
N2—C7—C8—C9	−154.71 (13)	C20—O1—C21—C22	−175.08 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1/N1/C1/C6/C7 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2ⁱ	0.95	2.38	3.311 (2)	166
C19—H19A···Cg2ⁱⁱ	0.95	2.59	3.4534 (18)	152
C21—H21A···Cg1ⁱⁱⁱ	0.99	2.64	3.5288 (15)	149

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇BrN₂O₂
M_r	421.29
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.3121 (2), 9.8136 (2), 11.8458 (2)
α, β, γ (°)	108.217 (1), 101.135 (1), 109.361 (1)
V (Å³)	915.39 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.27
Crystal size (mm)	0.42 × 0.33 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.450, 0.728
No. of measured, independent and observed [I > I > 2σ(I)] reflections	21718, 5326, 4846
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.071, 1.06
No. of reflections	5326
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.65

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1/N1/C1/C6/C7 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2ⁱ	0.95	2.38	3.311 (2)	166
C19—H19A···Cg2ⁱⁱ	0.95	2.59	3.4534 (18)	152
C21—H21A···Cg1ⁱⁱⁱ	0.99	2.64	3.5288 (15)	149

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

Footnotes

‡Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia for the Research University grants Nos. 1001/PFIZIK/811151 and 1001/PSK/8620012. The authors also thank Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Molecular Medicine, Universiti Sains Malaysia.

References

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