1-(2-Bromo­benz­yl)-3-isopropyl­benz­imid­azolin-2-one

Manjare, S.T.; Butcher, R.J.; Goel, N.; Singh, U.P.; Singh, H.B.

doi:10.1107/S1600536809042871

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2836

https://doi.org/10.1107/S1600536809042871

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1-(2-Bromobenzyl)-3-isopropylbenzimidazolin-2-one

Sudesh T. Manjare,^a Ray J. Butcher,^b Nidhi Goel,^c Udai P. Singh ^c and Harkesh B. Singh ^a ^*

^aDepartment of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India, ^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington DC 20059, USA, and ^cDepartment of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247 667, India
^*Correspondence e-mail: chhbsia@chem.iitb.ac.in

(Received 8 October 2009; accepted 19 October 2009; online 23 October 2009)

In the structure of the title compound, C₁₇H₁₇BrN₂O, the central phenyl and imidazol-2-one rings are coplanar (dihedral angle between planes of 0.73 (11)°). The angles subtended by the substituents on the N atoms of the imidazol-2-one ring range from 109.71 (14)° to 128.53 (15) due to steric hindrance of these substituents with the phenyl H atoms. The carbonyl O and Br both make two weak C—H⋯O and C—H⋯Br interactions with two adjacent molecules, thus forming an three-dimensional array.

Related literature

For benzimidazolones as precursors to important pharmacologically active compounds, see: Biagi et al. (2001 ). For the benzimidazolones as sources of stable carbenes, see: Albéniz et al. (2002 ); Denk et al. (2001 ); Jarrar & Fataftah (1977 ); Manjare et al. (2009 ); Çetinkaya et al. (1998 ). For the preparation, see: Kuhn et al. (1996 ).

Experimental

Crystal data

C₁₇H₁₇BrN₂O
M_r = 345.24
Monoclinic, P 2₁ /n
a = 12.1417 (3) Å
b = 10.1146 (3) Å
c = 12.2008 (3) Å
β = 95.763 (1)°
V = 1490.79 (7) Å³
Z = 4
Mo Kα radiation
μ = 2.76 mm⁻¹
T = 203 K
0.38 × 0.24 × 0.17 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.631, T_max = 0.746
26524 measured reflections
3771 independent reflections
3039 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.075
S = 0.99
3771 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.94	2.52	3.439 (2)	167
C9—H9⋯O1ⁱⁱ	0.94	2.50	3.374 (2)	154
C10—H10⋯Br1ⁱⁱⁱ	0.94	3.05	3.6457 (18)	123
C15—H15⋯Br1^iv	0.99	3.11	3.7941 (18)	128
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809042871/om2287sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809042871/om2287Isup2.hkl

checkCIF report

Comment top

There has been much interest in benzimidazolones as precursors to important pharmacologically active compounds (Biagi et al. 2001) and also as precursors to stable carbene derivatives (Albéniz et al.2002; Çetinkaya et al. 1998; Denk et al. 2001; Manjare et al. 2009). We report the structure of the title compound, C₁₇H₁₇BrN₂O, 1, prepared as part of a study of the reactivity of related selenones (Manjare et al. 2009) and with a view to stabilizing a monomeric selenium dioxide derivative. The product was obtained as the minor product from the selenone by reaction with H₂O₂ (Fig. 3).

As shown in Figure 1, the central phenyl and imidazol-2-one rings are coplanar (dihedral angle between planes of 0.73 (11)°). The benzoimidazol-2-one moiety is thus a planar system (r.m.s. deviation from plane of 0.0069 (1) Å). The phenyl ring of the substituent bromobenzyl group makes a dihedral angle of 80.64 (3) with this plane. In addition the C atoms attached to N1 and N2 are also coplanar with this ring. Within the imidazole ring the C—N and C—C distances range from 1.380 (2) to 1.402 (2) and thus are significantly shorter than single bonds. However, the bonds from N1 and N2 to the C atoms of the substituents are 1.468 (2) and 1.448 (2) which are in the range found for C—N single bonds. Thus the bond lengths in this ring are similar to those found in structures of dihydro-imidazol-2-one derivatives (Denk et al., 2001). The angles subtended by the substituents on the N's of the imidazol-2-one ring range from 109.71 (14)° to 128.53 (15) due to steric hindrance of these substituents with the phenyl H atoms.

The carbonyl O and Br both make two weak C–H···O and C–H···Br interactions with two adjacent molecules thus forming an 3-D array.

Related literature top

For benzimidazolones as precursors to important pharmacologically active compounds, see: Biagi et al. (2001). For the benzimidazolones as sources of stable carbenes, see: Albéniz et al. (2002); Denk et al. (2001); Jarrar & Fataftah (1977); Manjare et al. (2009); Çetinkaya et al. (1998). For the preparation, see: Kuhn et al. (1996).

Experimental top

The title compound was obtained by the addition of hydrogen peroxide (0.21 ml, 1.82 mmol) to the solution of selenone 2 (0.15 g, 0.37 mmol; Kuhn et al., 1996) in chloroform (15 ml) at room temperature. Sodium sulfate was added to the reaction mixture then the solution was filtered and evaporated. Compound 1 was obtained as minor product along with the compound 3 (Scheme 1).

Structure description top

The carbonyl O and Br both make two weak C–H···O and C–H···Br interactions with two adjacent molecules thus forming an 3-D array.

For benzimidazolones as precursors to important pharmacologically active compounds, see: Biagi et al. (2001). For the benzimidazolones as sources of stable carbenes, see: Albéniz et al. (2002); Denk et al. (2001); Jarrar & Fataftah (1977); Manjare et al. (2009); Çetinkaya et al. (1998). For the preparation, see: Kuhn et al. (1996).

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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of C₁₇H₁₇BrN₂O the showing the atom numbering scheme and 50% probability displacement ellipsoids.
	Fig. 2. The molecular packing for C₁₇H₁₇BrN₂O viewed down the c axis. The C—H···O interactions are shown by dashed lines.

1-(2-Bromobenzyl)-3-isopropylbenzimidazolin-2-one top

Crystal data top

C₁₇H₁₇BrN₂O	F(000) = 704
M_r = 345.24	D_x = 1.538 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9903 reflections
a = 12.1417 (3) Å	θ = 2.6–28.4°
b = 10.1146 (3) Å	µ = 2.76 mm⁻¹
c = 12.2008 (3) Å	T = 203 K
β = 95.763 (1)°	Prism, colorless
V = 1490.79 (7) Å³	0.38 × 0.24 × 0.17 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	3771 independent reflections
Radiation source: fine-focus sealed tube	3039 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
ω scans	θ_max = 28.6°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→16
T_min = 0.631, T_max = 0.746	k = −12→13
26524 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0471P)²] where P = (F_o² + 2F_c²)/3
3771 reflections	(Δ/σ)_max = 0.003
192 parameters	Δρ_max = 0.75 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₇H₁₇BrN₂O	V = 1490.79 (7) Å³
M_r = 345.24	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.1417 (3) Å	µ = 2.76 mm⁻¹
b = 10.1146 (3) Å	T = 203 K
c = 12.2008 (3) Å	0.38 × 0.24 × 0.17 mm
β = 95.763 (1)°

Data collection top

Bruker APEXII diffractometer	3771 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3039 reflections with I > 2σ(I)
T_min = 0.631, T_max = 0.746	R_int = 0.072
26524 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 0.99	Δρ_max = 0.75 e Å⁻³
3771 reflections	Δρ_min = −0.42 e Å⁻³
192 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
Br1	1.037577 (14)	0.582633 (17)	0.249055 (14)	0.01832 (8)
O1	0.61458 (11)	0.41194 (12)	0.14806 (11)	0.0195 (3)
N1	0.66453 (12)	0.58527 (14)	0.26835 (12)	0.0145 (3)
N2	0.48981 (12)	0.52025 (15)	0.25058 (12)	0.0141 (3)
C1	0.95844 (14)	0.46626 (18)	0.33498 (14)	0.0139 (4)
C2	1.01703 (15)	0.37113 (19)	0.39732 (14)	0.0178 (4)
H2	1.0942	0.3642	0.3966	0.021*
C3	0.96085 (16)	0.28571 (18)	0.46116 (15)	0.0199 (4)
H3	0.9996	0.2203	0.5041	0.024*
C4	0.84746 (16)	0.29766 (19)	0.46107 (15)	0.0200 (4)
H4	0.8092	0.2402	0.5045	0.024*
C5	0.78948 (15)	0.39346 (17)	0.39770 (15)	0.0172 (4)
H5	0.7124	0.4002	0.3989	0.021*
C6	0.84372 (14)	0.47977 (17)	0.33241 (14)	0.0140 (4)
C7	0.78243 (15)	0.58255 (17)	0.25879 (15)	0.0159 (4)
H7A	0.8135	0.6700	0.2777	0.019*
H7B	0.7945	0.5642	0.1820	0.019*
C8	0.60923 (14)	0.66479 (17)	0.33738 (13)	0.0137 (4)
C9	0.64598 (14)	0.76802 (17)	0.40571 (14)	0.0164 (4)
H9	0.7205	0.7948	0.4126	0.020*
C10	0.56824 (15)	0.83047 (18)	0.46372 (15)	0.0186 (4)
H10	0.5905	0.9015	0.5105	0.022*
C11	0.45850 (16)	0.79053 (18)	0.45424 (15)	0.0191 (4)
H11	0.4083	0.8339	0.4958	0.023*
C12	0.42093 (15)	0.68751 (17)	0.38446 (14)	0.0167 (4)
H12	0.3462	0.6617	0.3771	0.020*
C13	0.49817 (14)	0.62453 (18)	0.32639 (13)	0.0137 (4)
C14	0.59197 (14)	0.49597 (17)	0.21446 (14)	0.0147 (4)
C15	0.39093 (14)	0.44538 (17)	0.20836 (15)	0.0154 (4)
H15	0.4166	0.3691	0.1668	0.019*
C16	0.31692 (15)	0.52811 (19)	0.12750 (16)	0.0207 (4)
H16A	0.3569	0.5517	0.0654	0.031*
H16B	0.2951	0.6079	0.1638	0.031*
H16C	0.2515	0.4776	0.1017	0.031*
C17	0.32998 (17)	0.38940 (19)	0.30151 (16)	0.0214 (4)
H17A	0.3826	0.3466	0.3553	0.032*
H17B	0.2755	0.3254	0.2718	0.032*
H17C	0.2932	0.4606	0.3367	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01045 (11)	0.02172 (12)	0.02339 (12)	−0.00227 (7)	0.00473 (7)	0.00112 (7)
O1	0.0122 (7)	0.0221 (7)	0.0245 (7)	0.0023 (5)	0.0027 (5)	−0.0052 (5)
N1	0.0074 (7)	0.0186 (8)	0.0172 (7)	−0.0002 (6)	0.0004 (6)	0.0008 (6)
N2	0.0073 (7)	0.0155 (8)	0.0195 (8)	0.0003 (6)	0.0009 (6)	−0.0027 (6)
C1	0.0107 (9)	0.0150 (9)	0.0160 (8)	−0.0022 (7)	0.0015 (7)	−0.0036 (7)
C2	0.0112 (9)	0.0207 (10)	0.0212 (9)	0.0027 (8)	0.0002 (7)	−0.0020 (8)
C3	0.0187 (10)	0.0192 (10)	0.0212 (9)	0.0063 (8)	−0.0010 (8)	0.0013 (7)
C4	0.0209 (10)	0.0196 (10)	0.0195 (9)	−0.0021 (8)	0.0027 (7)	0.0027 (7)
C5	0.0102 (9)	0.0216 (10)	0.0197 (9)	−0.0006 (7)	0.0014 (7)	0.0010 (7)
C6	0.0104 (9)	0.0144 (9)	0.0170 (9)	−0.0003 (7)	0.0001 (7)	−0.0029 (7)
C7	0.0080 (9)	0.0197 (10)	0.0200 (9)	−0.0001 (7)	0.0010 (7)	0.0023 (7)
C8	0.0097 (8)	0.0154 (9)	0.0159 (8)	0.0029 (7)	0.0007 (6)	0.0050 (7)
C9	0.0125 (9)	0.0166 (9)	0.0193 (9)	−0.0035 (7)	−0.0028 (7)	0.0037 (7)
C10	0.0189 (10)	0.0164 (9)	0.0197 (9)	−0.0019 (8)	−0.0016 (7)	−0.0020 (7)
C11	0.0179 (10)	0.0181 (10)	0.0215 (9)	0.0044 (8)	0.0030 (7)	−0.0006 (7)
C12	0.0091 (8)	0.0183 (9)	0.0226 (9)	0.0003 (7)	0.0011 (7)	0.0003 (7)
C13	0.0133 (9)	0.0121 (9)	0.0152 (8)	−0.0003 (7)	−0.0003 (7)	0.0015 (7)
C14	0.0109 (9)	0.0154 (9)	0.0176 (9)	0.0024 (7)	0.0001 (7)	0.0029 (7)
C15	0.0089 (9)	0.0151 (9)	0.0222 (9)	−0.0018 (7)	0.0010 (7)	−0.0025 (7)
C16	0.0138 (9)	0.0215 (10)	0.0258 (10)	−0.0002 (8)	−0.0024 (8)	−0.0001 (8)
C17	0.0178 (10)	0.0178 (10)	0.0293 (10)	−0.0032 (8)	0.0056 (8)	0.0015 (8)

Geometric parameters (Å, º) top

Br1—C1	1.9000 (18)	C7—H7B	0.9800
O1—C14	1.224 (2)	C8—C9	1.382 (2)
N1—C14	1.381 (2)	C8—C13	1.402 (2)
N1—C8	1.386 (2)	C9—C10	1.387 (3)
N1—C7	1.448 (2)	C9—H9	0.9400
N2—C14	1.380 (2)	C10—C11	1.386 (3)
N2—C13	1.400 (2)	C10—H10	0.9400
N2—C15	1.468 (2)	C11—C12	1.393 (3)
C1—C2	1.379 (3)	C11—H11	0.9400
C1—C6	1.397 (2)	C12—C13	1.386 (2)
C2—C3	1.388 (3)	C12—H12	0.9400
C2—H2	0.9400	C15—C16	1.518 (3)
C3—C4	1.382 (3)	C15—C17	1.526 (2)
C3—H3	0.9400	C15—H15	0.9900
C4—C5	1.387 (3)	C16—H16A	0.9700
C4—H4	0.9400	C16—H16B	0.9700
C5—C6	1.391 (2)	C16—H16C	0.9700
C5—H5	0.9400	C17—H17A	0.9700
C6—C7	1.519 (2)	C17—H17B	0.9700
C7—H7A	0.9800	C17—H17C	0.9700

C14—N1—C8	110.12 (14)	C10—C9—H9	121.4
C14—N1—C7	122.53 (15)	C11—C10—C9	121.48 (17)
C8—N1—C7	127.09 (15)	C11—C10—H10	119.3
C14—N2—C13	109.71 (14)	C9—C10—H10	119.3
C14—N2—C15	121.73 (14)	C10—C11—C12	121.47 (17)
C13—N2—C15	128.53 (15)	C10—C11—H11	119.3
C2—C1—C6	122.59 (16)	C12—C11—H11	119.3
C2—C1—Br1	118.37 (13)	C13—C12—C11	117.35 (16)
C6—C1—Br1	119.04 (14)	C13—C12—H12	121.3
C1—C2—C3	119.25 (17)	C11—C12—H12	121.3
C1—C2—H2	120.4	C12—C13—N2	132.55 (16)
C3—C2—H2	120.4	C12—C13—C8	120.75 (16)
C4—C3—C2	119.41 (17)	N2—C13—C8	106.70 (15)
C4—C3—H3	120.3	O1—C14—N2	127.12 (17)
C2—C3—H3	120.3	O1—C14—N1	126.46 (16)
C3—C4—C5	120.77 (17)	N2—C14—N1	106.41 (15)
C3—C4—H4	119.6	N2—C15—C16	110.71 (14)
C5—C4—H4	119.6	N2—C15—C17	111.76 (15)
C4—C5—C6	120.97 (17)	C16—C15—C17	112.89 (15)
C4—C5—H5	119.5	N2—C15—H15	107.0
C6—C5—H5	119.5	C16—C15—H15	107.0
C5—C6—C1	117.00 (16)	C17—C15—H15	107.0
C5—C6—C7	122.41 (16)	C15—C16—H16A	109.5
C1—C6—C7	120.56 (16)	C15—C16—H16B	109.5
N1—C7—C6	113.26 (14)	H16A—C16—H16B	109.5
N1—C7—H7A	108.9	C15—C16—H16C	109.5
C6—C7—H7A	108.9	H16A—C16—H16C	109.5
N1—C7—H7B	108.9	H16B—C16—H16C	109.5
C6—C7—H7B	108.9	C15—C17—H17A	109.5
H7A—C7—H7B	107.7	C15—C17—H17B	109.5
C9—C8—N1	131.17 (16)	H17A—C17—H17B	109.5
C9—C8—C13	121.76 (16)	C15—C17—H17C	109.5
N1—C8—C13	107.05 (15)	H17A—C17—H17C	109.5
C8—C9—C10	117.18 (16)	H17B—C17—H17C	109.5
C8—C9—H9	121.4

C6—C1—C2—C3	−0.6 (3)	C10—C11—C12—C13	1.3 (3)
Br1—C1—C2—C3	179.61 (13)	C11—C12—C13—N2	−179.69 (18)
C1—C2—C3—C4	0.0 (3)	C11—C12—C13—C8	−0.6 (3)
C2—C3—C4—C5	0.3 (3)	C14—N2—C13—C12	178.84 (18)
C3—C4—C5—C6	0.2 (3)	C15—N2—C13—C12	0.7 (3)
C4—C5—C6—C1	−0.8 (3)	C14—N2—C13—C8	−0.3 (2)
C4—C5—C6—C7	177.72 (17)	C15—N2—C13—C8	−178.43 (16)
C2—C1—C6—C5	1.0 (3)	C9—C8—C13—C12	−0.1 (3)
Br1—C1—C6—C5	−179.22 (13)	N1—C8—C13—C12	−178.99 (15)
C2—C1—C6—C7	−177.50 (16)	C9—C8—C13—N2	179.17 (15)
Br1—C1—C6—C7	2.3 (2)	N1—C8—C13—N2	0.29 (18)
C14—N1—C7—C6	−80.5 (2)	C13—N2—C14—O1	−179.94 (17)
C8—N1—C7—C6	93.0 (2)	C15—N2—C14—O1	−1.7 (3)
C5—C6—C7—N1	3.0 (2)	C13—N2—C14—N1	0.22 (19)
C1—C6—C7—N1	−178.55 (15)	C15—N2—C14—N1	178.48 (14)
C14—N1—C8—C9	−178.90 (17)	C8—N1—C14—O1	−179.87 (17)
C7—N1—C8—C9	6.9 (3)	C7—N1—C14—O1	−5.4 (3)
C14—N1—C8—C13	−0.17 (19)	C8—N1—C14—N2	−0.03 (19)
C7—N1—C8—C13	−174.36 (15)	C7—N1—C14—N2	174.48 (15)
N1—C8—C9—C10	178.79 (17)	C14—N2—C15—C16	−104.36 (18)
C13—C8—C9—C10	0.2 (3)	C13—N2—C15—C16	73.5 (2)
C8—C9—C10—C11	0.4 (3)	C14—N2—C15—C17	128.87 (17)
C9—C10—C11—C12	−1.2 (3)	C13—N2—C15—C17	−53.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.94	2.52	3.439 (2)	167
C9—H9···O1ⁱⁱ	0.94	2.50	3.374 (2)	154
C10—H10···Br1ⁱⁱⁱ	0.94	3.05	3.6457 (18)	123
C15—H15···Br1^iv	0.99	3.11	3.7941 (18)	128

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+3/2, y+1/2, −z+1/2; (iii) x−1/2, −y+3/2, z+1/2; (iv) −x+3/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇BrN₂O
M_r	345.24
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	203
a, b, c (Å)	12.1417 (3), 10.1146 (3), 12.2008 (3)
β (°)	95.763 (1)
V (Å³)	1490.79 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.76
Crystal size (mm)	0.38 × 0.24 × 0.17

Data collection
Diffractometer	Bruker APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.631, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	26524, 3771, 3039
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.673

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.075, 0.99
No. of reflections	3771
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.42

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
C3—H3···O1ⁱ	0.94	2.52	3.439 (2)	167.0
C9—H9···O1ⁱⁱ	0.94	2.50	3.374 (2)	154.4
C10—H10···Br1ⁱⁱⁱ	0.94	3.05	3.6457 (18)	123.0
C15—H15···Br1^iv	0.99	3.11	3.7941 (18)	127.8

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+3/2, y+1/2, −z+1/2; (iii) x−1/2, −y+3/2, z+1/2; (iv) −x+3/2, y−1/2, −z+1/2.

Acknowledgements

HBS is grateful to the Department of Science and Technology (DST) for the award of a Ramanna Fellowship. STM thanks the CSIR for a JRF/SRF fellowship. RJB wishes to acknowledge the United States–India Educational Foundation for a Fulbright–Nehru Teaching Fellowship for the 2009–2010 academic year.

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