N-(4-Bromo-2-methyl­phen­yl)pivalamide

Qing, W.-X.; Zhang, W.

doi:10.1107/S1600536809034345

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2313

doi:10.1107/S1600536809034345

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N-(4-Bromo-2-methylphenyl)pivalamide

Wei-Xia Qing ^a ^* and Wei Zhang ^b

^aMedical College of Henan University, Henan University, Kaifeng 475004, People's Republic of China, and ^bDepartment of Pharmacy, Zhengzhou Railway Vocational and Technological College, Zhengzhou 450052, People's Republic of China
^*Correspondence e-mail: qingweixia2005@163.com

(Received 13 August 2009; accepted 27 August 2009; online 5 September 2009)

The conformation of the N—H bond in the title compound, C₁₂H₁₆BrNO, is syn to the ortho-methyl substituent. There are two unique molecules in the asymmetric unit. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules, forming infinite chains down [010].

Related literature

For a study of the effect of ring and side-chain substitution on the crystal structures of aromatic amides, see: Gowda et al. (2007 ). For related structures, see: Gowda et al. (2007a ,b ,c ).

Experimental

Crystal data

C₁₂H₁₆BrNO
M_r = 270.17
Monoclinic, P 2₁ /c
a = 11.764 (3) Å
b = 19.584 (5) Å
c = 12.956 (3) Å
β = 117.877 (19)°
V = 2638.5 (11) Å³
Z = 8
Mo Kα radiation
μ = 3.09 mm⁻¹
T = 293 K
0.42 × 0.37 × 0.32 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.357, T_max = 0.438
24481 measured reflections
4634 independent reflections
1875 reflections with I > 2σ(I)
R_int = 0.113

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.211
S = 1.01
4634 reflections
271 parameters
65 restraints
H-atom parameters constrained
Δρ_max = 0.90 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
N1—H1A⋯O2ⁱ	0.86	2.14	2.989 (8)	170
N2—H2B⋯O1ⁱⁱ	0.86	2.14	2.943 (8)	155
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034345/at2861sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809034345/at2861Isup2.hkl

checkCIF report

Comment top

As part of a study of the effect of ring and side chain substitutions on the crystal structures of chemically and biologically important class of compounds such as aromatic amides (Gowda, Kozisek et al., 2007), We now report the the crystal structure of the title compound, (I).

As shown in Fig.1, the title compound includes both the ortho-methyl and the p-Br-substituted phenyl group and an imide group. The title compound, (I), (Fig. 1) is structural isomer of both the 2-chloro and the 3-chloro substituent in N-(2,3-dichlorophenyl)acetamide (Gowda et al., 2007a) and N-(2,3-Dichlorophenyl)-2,2,2-trimethylacetamide (Gowda et al., 2007b). The conformation of the N–H bond in the title compound is syn to the ortho-methyl substituent, similar to that in both the 2-chloro and the 3-chloro-substituted amides, but in contrast to the anti conformation observed for the corresponding 3-chloro-substituted N-(3-Chlorophenyl)-2,2,2-trimethylacetamide (Gowda et al., 2007c). The amide H atom is involved in an intramolecular hydrogen bond with the O atom of the carbonyl group.

In the crystal structure, these molecules are linked into infinite one-dimensional chains by intermolecular N–H···O hydrogen bonds running along [010] direction (Fig. 2, Table 1).

Related literature top

For our study of the effect of ring and side-chain substitution on the crystal structures of aromatic amides, see: Gowda et al. (2007). For related structures, see: Gowda et al. (2007a,b,c).

Experimental top

2,2,2-Trimethyl-N-(2-methylphenyl)acetamide (0.95 5 g, 5 mmol) was added slowly by cannulation to a stirred suspension of p-nitroaniline (0.690 g, 3 mmol) in chloroform (50 ml) at room temperature. After stirring for 2 h the solution was quenched with saturated aqueous sodium bicarbonate solution (20 ml) the layers were separated and the aqueous layer was extracted with chloroform, the combined organic extracts were washed with water (20 ml), dried (MgSO₄) and evaporated under reduced pressure to give the crude product as viscous brown oil. Then purification by short column chromatography (chloroform) and recrystallization from chloroform gave the compound (I) as brown needles crystals (1.094 g, 81%).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. One-dimensional structure of (I) along [010] direction, Hydrogen bonds are shown in the dashing line.

N-(4-Bromo-2-methylphenyl)pivalamide top

Crystal data top

C₁₂H₁₆BrNO	F(000) = 1104
M_r = 270.17	D_x = 1.360 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3412 reflections
a = 11.764 (3) Å	θ = 2.2–19.4°
b = 19.584 (5) Å	µ = 3.09 mm⁻¹
c = 12.956 (3) Å	T = 293 K
β = 117.877 (19)°	Block, colourless
V = 2638.5 (11) Å³	0.42 × 0.37 × 0.32 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	4634 independent reflections
Radiation source: fine-focus sealed tube	1875 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.113
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −13→13
T_min = 0.357, T_max = 0.438	k = −23→23
24481 measured reflections	l = −15→15

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.211	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0858P)² + 4.1364P] where P = (F_o² + 2F_c²)/3
4634 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.90 e Å⁻³
65 restraints	Δρ_min = −0.70 e Å⁻³

Crystal data top

C₁₂H₁₆BrNO	V = 2638.5 (11) Å³
M_r = 270.17	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.764 (3) Å	µ = 3.09 mm⁻¹
b = 19.584 (5) Å	T = 293 K
c = 12.956 (3) Å	0.42 × 0.37 × 0.32 mm
β = 117.877 (19)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4634 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	1875 reflections with I > 2σ(I)
T_min = 0.357, T_max = 0.438	R_int = 0.113
24481 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	65 restraints
wR(F²) = 0.211	H-atom parameters constrained
S = 1.01	Δρ_max = 0.90 e Å⁻³
4634 reflections	Δρ_min = −0.70 e Å⁻³
271 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	0.96107 (9)	0.07766 (6)	1.22541 (8)	0.0941 (5)
Br2	0.00476 (11)	0.12629 (7)	−0.17802 (9)	0.1081 (5)
N1	0.4710 (6)	0.0356 (3)	0.7724 (5)	0.0521 (16)
H1A	0.4492	−0.0041	0.7412	0.063*
N2	0.4775 (6)	0.2083 (3)	0.2649 (5)	0.0665 (19)
H2B	0.4777	0.2497	0.2871	0.080*
O1	0.4160 (5)	0.1460 (3)	0.7638 (5)	0.0731 (17)
O2	0.5853 (6)	0.1099 (3)	0.3045 (5)	0.089 (2)
C1	0.8081 (8)	0.0605 (4)	1.0861 (7)	0.058 (2)
C2	0.6924 (8)	0.0724 (4)	1.0821 (6)	0.054 (2)
H2A	0.6884	0.0871	1.1486	0.065*
C3	0.5816 (8)	0.0626 (4)	0.9801 (6)	0.053 (2)
H3A	0.5024	0.0697	0.9780	0.064*
C4	0.5866 (7)	0.0423 (3)	0.8792 (6)	0.0465 (19)
C5	0.7052 (8)	0.0280 (4)	0.8833 (6)	0.052 (2)
C6	0.8141 (8)	0.0384 (4)	0.9878 (7)	0.060 (2)
H6A	0.8942	0.0303	0.9922	0.073*
C7	0.7118 (8)	0.0065 (5)	0.7749 (7)	0.081 (3)
H7A	0.7998	−0.0013	0.7934	0.121*
H7B	0.6764	0.0419	0.7171	0.121*
H7C	0.6634	−0.0348	0.7450	0.121*
C8	0.3938 (7)	0.0895 (4)	0.7178 (6)	0.0503 (18)
C9	0.2783 (8)	0.0769 (4)	0.5992 (6)	0.0594 (19)
C10	0.1890 (9)	0.0268 (5)	0.6154 (8)	0.094 (3)
H10A	0.1604	0.0462	0.6674	0.142*
H10B	0.2341	−0.0150	0.6478	0.142*
H10C	0.1159	0.0178	0.5412	0.142*
C11	0.2083 (9)	0.1434 (4)	0.5504 (8)	0.098 (3)
H11A	0.1838	0.1633	0.6048	0.147*
H11B	0.1328	0.1349	0.4777	0.147*
H11C	0.2638	0.1743	0.5376	0.147*
C12	0.3226 (10)	0.0449 (5)	0.5156 (7)	0.100 (3)
H12A	0.3794	0.0759	0.5047	0.150*
H12B	0.2491	0.0360	0.4416	0.150*
H12C	0.3670	0.0029	0.5481	0.150*
C13	0.1525 (9)	0.1490 (4)	−0.0371 (7)	0.062 (2)
C14	0.2695 (10)	0.1463 (4)	−0.0340 (7)	0.070 (2)
H14A	0.2766	0.1318	−0.0991	0.084*
C15	0.3774 (8)	0.1652 (4)	0.0661 (7)	0.067 (2)
H15A	0.4576	0.1640	0.0684	0.080*
C16	0.3671 (8)	0.1861 (4)	0.1639 (7)	0.053 (2)
C17	0.2495 (10)	0.1873 (4)	0.1621 (7)	0.064 (2)
C18	0.1419 (9)	0.1689 (4)	0.0592 (8)	0.068 (2)
H18A	0.0612	0.1701	0.0558	0.081*
C19	0.2349 (10)	0.2096 (5)	0.2664 (7)	0.093 (3)
H19A	0.1461	0.2068	0.2483	0.139*
H19B	0.2643	0.2558	0.2860	0.139*
H19C	0.2851	0.1803	0.3314	0.139*
C20	0.5824 (9)	0.1700 (5)	0.3295 (8)	0.074 (2)
C21	0.6956 (13)	0.2023 (7)	0.4300 (12)	0.149 (3)
C22	0.8063 (12)	0.1606 (6)	0.4813 (11)	0.152 (3)
H22A	0.7860	0.1187	0.5075	0.228*
H22B	0.8731	0.1840	0.5466	0.228*
H22C	0.8350	0.1507	0.4247	0.228*
C23	0.7298 (12)	0.2717 (6)	0.3915 (11)	0.152 (3)
H23A	0.8004	0.2926	0.4573	0.228*
H23B	0.6565	0.3015	0.3628	0.228*
H23C	0.7534	0.2637	0.3310	0.228*
C24	0.6485 (12)	0.2294 (6)	0.5109 (11)	0.154 (3)
H24A	0.6243	0.1921	0.5445	0.230*
H24B	0.5752	0.2583	0.4683	0.230*
H24C	0.7155	0.2553	0.5719	0.230*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0669 (7)	0.1288 (10)	0.0607 (6)	−0.0185 (6)	0.0082 (5)	−0.0030 (6)
Br2	0.0852 (8)	0.1378 (11)	0.0688 (7)	−0.0078 (7)	0.0089 (6)	−0.0144 (7)
N1	0.059 (4)	0.042 (4)	0.045 (4)	0.005 (3)	0.016 (3)	−0.001 (3)
N2	0.073 (5)	0.048 (4)	0.059 (4)	0.004 (4)	0.014 (4)	−0.010 (4)
O1	0.082 (4)	0.042 (3)	0.064 (3)	0.003 (3)	0.008 (3)	−0.005 (3)
O2	0.096 (5)	0.045 (4)	0.084 (4)	0.010 (3)	0.006 (4)	−0.018 (3)
C1	0.062 (6)	0.056 (5)	0.053 (5)	0.006 (4)	0.024 (4)	0.005 (4)
C2	0.063 (6)	0.059 (5)	0.037 (4)	0.003 (4)	0.021 (4)	0.000 (4)
C3	0.055 (5)	0.055 (5)	0.048 (5)	0.001 (4)	0.024 (4)	−0.001 (4)
C4	0.053 (5)	0.037 (4)	0.043 (5)	0.003 (4)	0.017 (4)	0.001 (4)
C5	0.056 (6)	0.053 (5)	0.049 (5)	0.000 (4)	0.026 (4)	−0.004 (4)
C6	0.047 (5)	0.068 (6)	0.066 (6)	0.002 (4)	0.026 (5)	0.008 (5)
C7	0.078 (7)	0.100 (7)	0.083 (6)	−0.002 (5)	0.052 (6)	−0.023 (6)
C8	0.059 (4)	0.047 (5)	0.044 (4)	0.000 (4)	0.023 (3)	−0.003 (4)
C9	0.069 (5)	0.049 (4)	0.044 (4)	0.001 (3)	0.013 (3)	−0.002 (3)
C10	0.078 (6)	0.100 (7)	0.081 (6)	−0.023 (5)	0.016 (5)	−0.001 (5)
C11	0.093 (7)	0.069 (5)	0.072 (6)	0.015 (5)	−0.010 (5)	0.001 (4)
C12	0.120 (8)	0.120 (7)	0.050 (5)	0.026 (6)	0.031 (5)	−0.012 (5)
C13	0.072 (7)	0.060 (6)	0.050 (5)	−0.003 (5)	0.026 (5)	0.000 (4)
C14	0.089 (7)	0.071 (6)	0.048 (5)	0.011 (5)	0.031 (5)	−0.004 (4)
C15	0.066 (6)	0.070 (6)	0.063 (6)	0.007 (5)	0.029 (5)	−0.011 (5)
C16	0.057 (6)	0.038 (5)	0.057 (5)	0.006 (4)	0.020 (5)	0.001 (4)
C17	0.095 (7)	0.049 (5)	0.048 (5)	−0.012 (5)	0.033 (5)	−0.003 (4)
C18	0.074 (6)	0.069 (6)	0.074 (6)	−0.010 (5)	0.045 (6)	−0.002 (5)
C19	0.118 (8)	0.112 (8)	0.069 (6)	−0.025 (7)	0.061 (6)	−0.019 (6)
C20	0.087 (6)	0.054 (5)	0.072 (5)	0.005 (5)	0.029 (5)	−0.004 (4)
C21	0.125 (5)	0.105 (5)	0.136 (5)	−0.001 (4)	−0.006 (4)	−0.032 (4)
C22	0.126 (6)	0.106 (5)	0.138 (6)	0.000 (4)	−0.010 (4)	−0.032 (4)
C23	0.126 (6)	0.108 (5)	0.140 (6)	−0.004 (4)	−0.007 (4)	−0.029 (4)
C24	0.129 (6)	0.112 (5)	0.137 (6)	−0.002 (4)	−0.006 (4)	−0.032 (4)

Geometric parameters (Å, º) top

Br1—C1	1.889 (8)	C11—H11B	0.9600
Br2—C13	1.894 (8)	C11—H11C	0.9600
N1—C8	1.355 (9)	C12—H12A	0.9600
N1—C4	1.422 (9)	C12—H12B	0.9600
N1—H1A	0.8600	C12—H12C	0.9600
N2—C20	1.349 (10)	C13—C14	1.359 (11)
N2—C16	1.413 (9)	C13—C18	1.368 (11)
N2—H2B	0.8600	C14—C15	1.375 (11)
O1—C8	1.225 (8)	C14—H14A	0.9300
O2—C20	1.226 (9)	C15—C16	1.389 (11)
C1—C2	1.358 (10)	C15—H15A	0.9300
C1—C6	1.377 (11)	C16—C17	1.374 (11)
C2—C3	1.368 (10)	C17—C18	1.390 (11)
C2—H2A	0.9300	C17—C19	1.503 (11)
C3—C4	1.393 (10)	C18—H18A	0.9300
C3—H3A	0.9300	C19—H19A	0.9600
C4—C5	1.399 (10)	C19—H19B	0.9600
C5—C6	1.377 (10)	C19—H19C	0.9600
C5—C7	1.503 (10)	C20—C21	1.499 (14)
C6—H6A	0.9300	C21—C22	1.412 (15)
C7—H7A	0.9600	C21—C24	1.494 (18)
C7—H7B	0.9600	C21—C23	1.564 (17)
C7—H7C	0.9600	C22—H22A	0.9600
C8—C9	1.521 (10)	C22—H22B	0.9600
C9—C11	1.513 (10)	C22—H22C	0.9600
C9—C10	1.522 (11)	C23—H23A	0.9600
C9—C12	1.539 (11)	C23—H23B	0.9600
C10—H10A	0.9600	C23—H23C	0.9600
C10—H10B	0.9600	C24—H24A	0.9600
C10—H10C	0.9600	C24—H24B	0.9600
C11—H11A	0.9600	C24—H24C	0.9600

C8—N1—C4	122.7 (6)	C9—C12—H12C	109.5
C8—N1—H1A	118.7	H12A—C12—H12C	109.5
C4—N1—H1A	118.7	H12B—C12—H12C	109.5
C20—N2—C16	125.6 (7)	C14—C13—C18	120.5 (8)
C20—N2—H2B	117.2	C14—C13—Br2	118.6 (7)
C16—N2—H2B	117.2	C18—C13—Br2	120.8 (7)
C2—C1—C6	120.1 (8)	C13—C14—C15	119.5 (8)
C2—C1—Br1	119.7 (6)	C13—C14—H14A	120.3
C6—C1—Br1	120.1 (7)	C15—C14—H14A	120.3
C1—C2—C3	119.9 (7)	C14—C15—C16	120.3 (8)
C1—C2—H2A	120.1	C14—C15—H15A	119.8
C3—C2—H2A	120.1	C16—C15—H15A	119.8
C2—C3—C4	120.5 (8)	C17—C16—C15	120.4 (8)
C2—C3—H3A	119.7	C17—C16—N2	119.5 (8)
C4—C3—H3A	119.7	C15—C16—N2	120.1 (8)
C3—C4—C5	120.0 (7)	C16—C17—C18	118.0 (8)
C3—C4—N1	119.9 (7)	C16—C17—C19	121.8 (8)
C5—C4—N1	120.1 (7)	C18—C17—C19	120.1 (9)
C6—C5—C4	117.5 (7)	C13—C18—C17	121.2 (8)
C6—C5—C7	122.0 (8)	C13—C18—H18A	119.4
C4—C5—C7	120.5 (7)	C17—C18—H18A	119.4
C5—C6—C1	121.9 (8)	C17—C19—H19A	109.5
C5—C6—H6A	119.0	C17—C19—H19B	109.5
C1—C6—H6A	119.0	H19A—C19—H19B	109.5
C5—C7—H7A	109.5	C17—C19—H19C	109.5
C5—C7—H7B	109.5	H19A—C19—H19C	109.5
H7A—C7—H7B	109.5	H19B—C19—H19C	109.5
C5—C7—H7C	109.5	O2—C20—N2	120.0 (8)
H7A—C7—H7C	109.5	O2—C20—C21	120.7 (9)
H7B—C7—H7C	109.5	N2—C20—C21	119.2 (9)
O1—C8—N1	120.7 (7)	C22—C21—C24	116.0 (13)
O1—C8—C9	121.6 (7)	C22—C21—C20	114.5 (11)
N1—C8—C9	117.7 (7)	C24—C21—C20	106.8 (12)
C11—C9—C8	109.7 (6)	C22—C21—C23	109.6 (13)
C11—C9—C10	109.6 (8)	C24—C21—C23	98.6 (10)
C8—C9—C10	108.3 (6)	C20—C21—C23	110.2 (10)
C11—C9—C12	110.7 (7)	C21—C22—H22A	109.5
C8—C9—C12	109.9 (7)	C21—C22—H22B	109.5
C10—C9—C12	108.5 (7)	H22A—C22—H22B	109.5
C9—C10—H10A	109.5	C21—C22—H22C	109.5
C9—C10—H10B	109.5	H22A—C22—H22C	109.5
H10A—C10—H10B	109.5	H22B—C22—H22C	109.5
C9—C10—H10C	109.5	C21—C23—H23A	109.5
H10A—C10—H10C	109.5	C21—C23—H23B	109.5
H10B—C10—H10C	109.5	H23A—C23—H23B	109.5
C9—C11—H11A	109.5	C21—C23—H23C	109.5
C9—C11—H11B	109.5	H23A—C23—H23C	109.5
H11A—C11—H11B	109.5	H23B—C23—H23C	109.5
C9—C11—H11C	109.5	C21—C24—H24A	109.5
H11A—C11—H11C	109.5	C21—C24—H24B	109.5
H11B—C11—H11C	109.5	H24A—C24—H24B	109.5
C9—C12—H12A	109.5	C21—C24—H24C	109.5
C9—C12—H12B	109.5	H24A—C24—H24C	109.5
H12A—C12—H12B	109.5	H24B—C24—H24C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86	2.14	2.989 (8)	170
N2—H2B···O1ⁱⁱ	0.86	2.14	2.943 (8)	155

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₆BrNO
M_r	270.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.764 (3), 19.584 (5), 12.956 (3)
β (°)	117.877 (19)
V (Å³)	2638.5 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.09
Crystal size (mm)	0.42 × 0.37 × 0.32

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.357, 0.438
No. of measured, independent and observed [I > 2σ(I)] reflections	24481, 4634, 1875
R_int	0.113
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.211, 1.01
No. of reflections	4634
No. of parameters	271
No. of restraints	65
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.90, −0.70

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86	2.14	2.989 (8)	169.5
N2—H2B···O1ⁱⁱ	0.86	2.14	2.943 (8)	154.8

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

References

Bruker (2001). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gowda, B. T., Foro, S. & Fuess, H. (2007a). Acta Cryst. E63, o2631–o2632. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S. & Fuess, H. (2007b). Acta Cryst. E63, o3788. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S. & Fuess, H. (2007c). Acta Cryst. E63, o2331–o2332. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Kozisek, J., Tokarčík, M. & Fuess, H. (2007). Acta Cryst. E63, o1983–o1984. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 10| October 2009| Page o2313

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