2,2,2-Tribromo-N-(2-methyl­phen­yl)acetamide

Gowda, B.T.; Foro, S.; Suchetan, P.A.; Fuess, H.

doi:10.1107/S1600536810009852

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o884

doi:10.1107/S1600536810009852

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2,2,2-Tribromo-N-(2-methylphenyl)acetamide

B. Thimme Gowda,^a ^* Sabine Foro,^b P. A. Suchetan ^a and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 19 February 2010; accepted 16 March 2010; online 20 March 2010)

The asymmetric unit of the title compound, C₉H₈Br₃NO, contains two independent molecules. Intramolecular N—H⋯Br hydrogen bonds are present in both molecules. In the crystal, molecules are packed into columnar chains by intermolecular N—H⋯O hydrogen bonds.

Related literature

For preparation of the title compound, see: Gowda et al. (2003 ). For background to our study of the effect of ring and side-chain substituents on the solid state structures of N-aromatic amides and for related structures, see: Brown (1966 ); Gowda et al. (2009 , 2010 ).

Experimental

Crystal data

C₉H₈Br₃NO
M_r = 385.89
Monoclinic, P 2₁ /c
a = 9.949 (2) Å
b = 21.429 (4) Å
c = 11.653 (2) Å
β = 107.69 (1)°
V = 2366.9 (8) Å³
Z = 8
Cu Kα radiation
μ = 12.40 mm⁻¹
T = 299 K
0.55 × 0.28 × 0.28 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.056, T_max = 0.129
5721 measured reflections
4204 independent reflections
3666 reflections with I > 2σ(I)
R_int = 0.149
3 standard reflections every 120 min intensity decay: 1.5%

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.212
S = 1.05
4204 reflections
260 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.77 e Å⁻³
Δρ_min = −1.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2	0.84 (4)	2.28 (6)	3.031 (8)	149 (9)
N1—H1N⋯Br1	0.84 (4)	2.53 (9)	3.048 (7)	120 (8)
N2—H2N⋯O1ⁱ	0.85 (4)	2.23 (7)	2.928 (9)	139 (9)
N2—H2N⋯Br5	0.85 (4)	2.50 (9)	3.036 (6)	122 (8)
Symmetry code: (i) x+1, y, z.

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810009852/pk2229sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810009852/pk2229Isup2.hkl

checkCIF report

Comment top

As part of a study of the effect of ring and the side chain substituents on the solid state structures of N-aromatic amides (Gowda et al., 2009, 2010), the structure of 2,2,2-tribromo-N-(2-methylphenyl)acetamide has been determined (Fig.1). The asymmetric unit of the structure contains two independent molecules. The conformation of the N—H bond in the structure is anti to the C=O bond in the side chain, similar to that observed in 2,2,2-tribromo-N-(phenyl)acetamide, 2,2,2-tribromo-N-(2-chlorophenyl)acetamide (Gowda et al., 2010), 2,2,2-tribromo-N-(3-methylphenyl)acetamide (Gowda et al., 2009) and other amides (Brown, 1966). The structure of the title compound shows both intramolecular N—H···Br and intermolecular N—H···O H-bonding. A packing diagram of molecules showing the hydrogen bonds N1—H1N···O2 and N2—H2N···O1 (Table 1) involved in the formation of molecular chains is shown in Fig. 2.

Related literature top

For preparation of the title compound, see: Gowda et al. (2003). For background to our study of the effect of ring and side-chain substituents on the solid state structures of N-aromatic amides and for related structures, see: Brown (1966); Gowda et al. (2009, 2010).

Experimental top

The title compound was prepared from o-toluidine, tribromoacetic acid and phosphorylchloride according to the literature method (Gowda et al., 2003). The purity of the compound was checked by determining its melting point. It was further characterized by recording its infrared spectra. Single crystals of the title compound used for X-ray diffraction studies were obtained by a slow evaporation of its solution in petroleum ether at room temperature.

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are represented as small spheres of arbitrary radius.
	Fig. 2. Molecular packing in the structure of the title compound with hydrogen bonds shown as dashed lines.

2,2,2-Tribromo-N-(2-methylphenyl)acetamide top

Crystal data top

C₉H₈Br₃NO	F(000) = 1456
M_r = 385.89	D_x = 2.166 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.949 (2) Å	θ = 4.1–18.8°
b = 21.429 (4) Å	µ = 12.40 mm⁻¹
c = 11.653 (2) Å	T = 299 K
β = 107.69 (1)°	Rod, colourless
V = 2366.9 (8) Å³	0.55 × 0.28 × 0.28 mm
Z = 8

Data collection top

Enraf–Nonius CAD-4 diffractometer	3666 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.149
Graphite monochromator	θ_max = 67.0°, θ_min = 4.1°
ω/2θ scans	h = −11→3
Absorption correction: ψ scan (North et al., 1968)	k = −25→0
T_min = 0.056, T_max = 0.129	l = −13→13
5721 measured reflections	3 standard reflections every 120 min
4204 independent reflections	intensity decay: 1.5%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.073	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.212	w = 1/[σ²(F_o²) + (0.1206P)² + 14.5272P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
4204 reflections	Δρ_max = 1.77 e Å⁻³
260 parameters	Δρ_min = −1.34 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00203 (19)

Crystal data top

C₉H₈Br₃NO	V = 2366.9 (8) Å³
M_r = 385.89	Z = 8
Monoclinic, P2₁/c	Cu Kα radiation
a = 9.949 (2) Å	µ = 12.40 mm⁻¹
b = 21.429 (4) Å	T = 299 K
c = 11.653 (2) Å	0.55 × 0.28 × 0.28 mm
β = 107.69 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	3666 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.149
T_min = 0.056, T_max = 0.129	3 standard reflections every 120 min
5721 measured reflections	intensity decay: 1.5%
4204 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	2 restraints
wR(F²) = 0.212	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.1206P)² + 14.5272P] where P = (F_o² + 2F_c²)/3
4204 reflections	Δρ_max = 1.77 e Å⁻³
260 parameters	Δρ_min = −1.34 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	−0.0153 (8)	0.3501 (4)	0.6789 (7)	0.0360 (16)
C2	0.0276 (9)	0.3149 (4)	0.7841 (7)	0.0428 (18)
C3	0.0010 (11)	0.2519 (5)	0.7730 (10)	0.059 (2)
H3	0.0286	0.2272	0.8418	0.071*
C4	−0.0656 (12)	0.2238 (5)	0.6631 (12)	0.063 (3)
H4	−0.0811	0.1809	0.6587	0.076*
C5	−0.1078 (11)	0.2593 (5)	0.5620 (11)	0.061 (3)
H5	−0.1535	0.2410	0.4881	0.073*
C6	−0.0822 (9)	0.3234 (4)	0.5694 (8)	0.0453 (19)
H6	−0.1104	0.3480	0.5004	0.054*
C7	−0.0894 (7)	0.4574 (3)	0.6711 (7)	0.0335 (15)
C8	−0.0422 (8)	0.5264 (4)	0.6954 (6)	0.0356 (15)
C9	0.0957 (12)	0.3450 (6)	0.9028 (9)	0.065 (3)
H9A	0.0317	0.3747	0.9196	0.078*
H9B	0.1800	0.3661	0.9006	0.078*
H9C	0.1191	0.3138	0.9647	0.078*
N1	0.0124 (6)	0.4153 (3)	0.6855 (6)	0.0369 (14)
H1N	0.095 (5)	0.429 (4)	0.700 (9)	0.044*
O1	−0.2153 (6)	0.4451 (3)	0.6442 (7)	0.0537 (16)
Br1	0.14164 (9)	0.54417 (4)	0.68400 (10)	0.0519 (3)
Br2	−0.04344 (14)	0.54241 (6)	0.85827 (9)	0.0703 (4)
Br3	−0.17695 (10)	0.57952 (5)	0.58669 (10)	0.0581 (4)
C10	0.5167 (7)	0.4983 (4)	0.7302 (7)	0.0350 (15)
C11	0.5752 (9)	0.5236 (4)	0.8425 (8)	0.0464 (19)
C12	0.5630 (12)	0.5873 (6)	0.8526 (11)	0.068 (3)
H12	0.6000	0.6059	0.9277	0.082*
C13	0.4978 (12)	0.6242 (5)	0.7546 (13)	0.069 (3)
H13	0.4913	0.6671	0.7636	0.082*
C14	0.4424 (10)	0.5969 (5)	0.6435 (11)	0.059 (3)
H14	0.3986	0.6215	0.5769	0.070*
C15	0.4512 (9)	0.5338 (4)	0.6306 (8)	0.0439 (18)
H15	0.4136	0.5152	0.5555	0.053*
C16	0.4364 (7)	0.3930 (3)	0.7382 (7)	0.0338 (15)
C17	0.4640 (7)	0.3218 (4)	0.7325 (7)	0.0354 (16)
C18	0.6471 (13)	0.4835 (7)	0.9492 (10)	0.075 (3)
H18A	0.7243	0.4616	0.9341	0.090*
H18B	0.5809	0.4539	0.9624	0.090*
H18C	0.6822	0.5093	1.0194	0.090*
N2	0.5275 (7)	0.4317 (3)	0.7144 (6)	0.0370 (14)
H2N	0.591 (8)	0.416 (4)	0.689 (8)	0.044*
O2	0.3318 (7)	0.4088 (3)	0.7643 (7)	0.0539 (16)
Br4	0.48061 (16)	0.28822 (6)	0.88797 (10)	0.0740 (4)
Br5	0.63133 (11)	0.30070 (5)	0.68942 (12)	0.0628 (4)
Br6	0.30461 (11)	0.28588 (5)	0.61417 (12)	0.0677 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.033 (3)	0.036 (4)	0.042 (4)	0.005 (3)	0.016 (3)	0.006 (3)
C2	0.046 (4)	0.045 (5)	0.044 (4)	0.005 (4)	0.024 (3)	0.004 (3)
C3	0.070 (6)	0.045 (5)	0.072 (7)	0.013 (5)	0.034 (5)	0.019 (5)
C4	0.079 (7)	0.028 (5)	0.096 (8)	−0.001 (4)	0.046 (6)	−0.004 (5)
C5	0.064 (6)	0.043 (5)	0.079 (7)	−0.008 (4)	0.029 (5)	−0.022 (5)
C6	0.049 (4)	0.046 (5)	0.040 (4)	0.006 (4)	0.013 (3)	0.004 (3)
C7	0.035 (4)	0.027 (4)	0.041 (4)	−0.002 (3)	0.015 (3)	0.007 (3)
C8	0.038 (4)	0.040 (4)	0.032 (3)	0.001 (3)	0.015 (3)	0.000 (3)
C9	0.069 (6)	0.078 (8)	0.043 (5)	−0.004 (6)	0.010 (4)	0.010 (5)
N1	0.026 (3)	0.039 (4)	0.044 (4)	−0.002 (3)	0.008 (2)	0.008 (3)
O1	0.038 (3)	0.036 (3)	0.087 (5)	0.002 (2)	0.019 (3)	0.004 (3)
Br1	0.0403 (5)	0.0394 (6)	0.0790 (7)	−0.0034 (3)	0.0227 (4)	0.0118 (4)
Br2	0.1006 (9)	0.0767 (8)	0.0412 (6)	−0.0170 (6)	0.0330 (5)	−0.0102 (5)
Br3	0.0506 (5)	0.0381 (6)	0.0706 (7)	0.0069 (4)	−0.0041 (4)	0.0126 (4)
C10	0.032 (3)	0.030 (4)	0.045 (4)	−0.005 (3)	0.015 (3)	0.000 (3)
C11	0.041 (4)	0.045 (5)	0.052 (5)	−0.006 (4)	0.011 (3)	−0.005 (4)
C12	0.070 (6)	0.060 (7)	0.071 (7)	−0.017 (5)	0.014 (5)	−0.035 (5)
C13	0.068 (6)	0.029 (5)	0.107 (9)	−0.008 (4)	0.025 (6)	−0.006 (5)
C14	0.055 (5)	0.037 (5)	0.085 (7)	0.008 (4)	0.023 (5)	0.019 (5)
C15	0.044 (4)	0.040 (5)	0.047 (4)	−0.004 (3)	0.015 (3)	0.001 (3)
C16	0.033 (3)	0.027 (4)	0.042 (4)	0.009 (3)	0.012 (3)	0.001 (3)
C17	0.030 (3)	0.027 (4)	0.049 (4)	0.002 (3)	0.012 (3)	0.003 (3)
C18	0.074 (7)	0.090 (9)	0.046 (5)	−0.002 (6)	−0.003 (5)	0.006 (5)
N2	0.041 (3)	0.023 (3)	0.053 (4)	0.005 (3)	0.023 (3)	0.001 (3)
O2	0.049 (3)	0.031 (3)	0.091 (5)	0.003 (3)	0.036 (3)	0.000 (3)
Br4	0.1248 (11)	0.0556 (7)	0.0497 (6)	0.0301 (6)	0.0387 (6)	0.0187 (5)
Br5	0.0549 (6)	0.0364 (6)	0.1123 (9)	0.0086 (4)	0.0482 (6)	−0.0001 (5)
Br6	0.0544 (6)	0.0506 (7)	0.0818 (8)	0.0001 (4)	−0.0036 (5)	−0.0176 (5)

Geometric parameters (Å, º) top

C1—C6	1.371 (12)	C10—C11	1.372 (12)
C1—C2	1.391 (11)	C10—C15	1.375 (12)
C1—N1	1.423 (11)	C10—N2	1.446 (10)
C2—C3	1.374 (14)	C11—C12	1.377 (15)
C2—C9	1.490 (14)	C11—C18	1.503 (14)
C3—C4	1.389 (17)	C12—C13	1.378 (18)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.358 (17)	C13—C14	1.374 (17)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.396 (14)	C14—C15	1.366 (13)
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	C15—H15	0.9300
C7—O1	1.224 (9)	C16—O2	1.217 (9)
C7—N1	1.329 (10)	C16—N2	1.320 (10)
C7—C8	1.552 (11)	C16—C17	1.554 (10)
C8—Br1	1.912 (7)	C17—Br4	1.910 (8)
C8—Br3	1.914 (8)	C17—Br6	1.918 (8)
C8—Br2	1.932 (7)	C17—Br5	1.933 (7)
C9—H9A	0.9600	C18—H18A	0.9600
C9—H9B	0.9600	C18—H18B	0.9600
C9—H9C	0.9600	C18—H18C	0.9600
N1—H1N	0.84 (4)	N2—H2N	0.85 (4)

C6—C1—C2	121.8 (8)	C11—C10—C15	122.7 (8)
C6—C1—N1	119.4 (7)	C11—C10—N2	119.0 (7)
C2—C1—N1	118.8 (7)	C15—C10—N2	118.3 (7)
C3—C2—C1	116.8 (8)	C10—C11—C12	116.8 (9)
C3—C2—C9	122.2 (9)	C10—C11—C18	121.3 (9)
C1—C2—C9	121.0 (9)	C12—C11—C18	121.9 (10)
C2—C3—C4	122.5 (9)	C11—C12—C13	121.9 (10)
C2—C3—H3	118.7	C11—C12—H12	119.0
C4—C3—H3	118.7	C13—C12—H12	119.0
C5—C4—C3	119.5 (9)	C14—C13—C12	119.3 (9)
C5—C4—H4	120.3	C14—C13—H13	120.4
C3—C4—H4	120.3	C12—C13—H13	120.4
C4—C5—C6	119.7 (10)	C15—C14—C13	120.3 (10)
C4—C5—H5	120.1	C15—C14—H14	119.9
C6—C5—H5	120.1	C13—C14—H14	119.9
C1—C6—C5	119.7 (9)	C14—C15—C10	119.0 (9)
C1—C6—H6	120.2	C14—C15—H15	120.5
C5—C6—H6	120.2	C10—C15—H15	120.5
O1—C7—N1	124.6 (7)	O2—C16—N2	124.8 (7)
O1—C7—C8	118.8 (7)	O2—C16—C17	117.4 (7)
N1—C7—C8	116.5 (6)	N2—C16—C17	117.8 (6)
C7—C8—Br1	114.8 (5)	C16—C17—Br4	107.1 (5)
C7—C8—Br3	109.5 (5)	C16—C17—Br6	107.8 (5)
Br1—C8—Br3	109.2 (4)	Br4—C17—Br6	110.2 (4)
C7—C8—Br2	104.8 (5)	C16—C17—Br5	114.7 (5)
Br1—C8—Br2	109.0 (4)	Br4—C17—Br5	109.0 (4)
Br3—C8—Br2	109.4 (4)	Br6—C17—Br5	108.0 (4)
C2—C9—H9A	109.5	C11—C18—H18A	109.5
C2—C9—H9B	109.5	C11—C18—H18B	109.5
H9A—C9—H9B	109.5	H18A—C18—H18B	109.5
C2—C9—H9C	109.5	C11—C18—H18C	109.5
H9A—C9—H9C	109.5	H18A—C18—H18C	109.5
H9B—C9—H9C	109.5	H18B—C18—H18C	109.5
C7—N1—C1	122.2 (6)	C16—N2—C10	120.8 (6)
C7—N1—H1N	117 (7)	C16—N2—H2N	117 (7)
C1—N1—H1N	120 (7)	C10—N2—H2N	122 (7)

C6—C1—C2—C3	0.6 (12)	C15—C10—C11—C12	1.4 (12)
N1—C1—C2—C3	−178.8 (7)	N2—C10—C11—C12	179.5 (8)
C6—C1—C2—C9	−177.9 (8)	C15—C10—C11—C18	−179.4 (9)
N1—C1—C2—C9	2.7 (11)	N2—C10—C11—C18	−1.3 (12)
C1—C2—C3—C4	−0.1 (14)	C10—C11—C12—C13	−1.2 (15)
C9—C2—C3—C4	178.4 (9)	C18—C11—C12—C13	179.7 (11)
C2—C3—C4—C5	−0.6 (16)	C11—C12—C13—C14	0.3 (17)
C3—C4—C5—C6	0.8 (15)	C12—C13—C14—C15	0.4 (16)
C2—C1—C6—C5	−0.4 (12)	C13—C14—C15—C10	−0.2 (14)
N1—C1—C6—C5	179.0 (8)	C11—C10—C15—C14	−0.7 (12)
C4—C5—C6—C1	−0.3 (14)	N2—C10—C15—C14	−178.9 (7)
O1—C7—C8—Br1	−160.3 (6)	O2—C16—C17—Br4	−59.3 (8)
N1—C7—C8—Br1	21.9 (8)	N2—C16—C17—Br4	120.7 (6)
O1—C7—C8—Br3	−37.2 (9)	O2—C16—C17—Br6	59.3 (8)
N1—C7—C8—Br3	145.1 (6)	N2—C16—C17—Br6	−120.7 (6)
O1—C7—C8—Br2	80.1 (8)	O2—C16—C17—Br5	179.6 (6)
N1—C7—C8—Br2	−97.6 (6)	N2—C16—C17—Br5	−0.3 (9)
O1—C7—N1—C1	−4.5 (12)	O2—C16—N2—C10	6.5 (12)
C8—C7—N1—C1	173.0 (6)	C17—C16—N2—C10	−173.5 (7)
C6—C1—N1—C7	71.7 (10)	C11—C10—N2—C16	83.9 (9)
C2—C1—N1—C7	−108.9 (8)	C15—C10—N2—C16	−97.9 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.84 (4)	2.28 (6)	3.031 (8)	149 (9)
N1—H1N···Br1	0.84 (4)	2.53 (9)	3.048 (7)	120 (8)
N2—H2N···O1ⁱ	0.85 (4)	2.23 (7)	2.928 (9)	139 (9)
N2—H2N···Br5	0.85 (4)	2.50 (9)	3.036 (6)	122 (8)

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₉H₈Br₃NO
M_r	385.89
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	299
a, b, c (Å)	9.949 (2), 21.429 (4), 11.653 (2)
β (°)	107.69 (1)
V (Å³)	2366.9 (8)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	12.40
Crystal size (mm)	0.55 × 0.28 × 0.28

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.056, 0.129
No. of measured, independent and observed [I > 2σ(I)] reflections	5721, 4204, 3666
R_int	0.149
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.212, 1.05
No. of reflections	4204
No. of parameters	260
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.1206P)² + 14.5272P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.77, −1.34

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), 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—H1N···O2	0.84 (4)	2.28 (6)	3.031 (8)	149 (9)
N1—H1N···Br1	0.84 (4)	2.53 (9)	3.048 (7)	120 (8)
N2—H2N···O1ⁱ	0.85 (4)	2.23 (7)	2.928 (9)	139 (9)
N2—H2N···Br5	0.85 (4)	2.50 (9)	3.036 (6)	122 (8)

Symmetry code: (i) x+1, y, z.

Acknowledgements

PAS thanks the Council of Scientific and Industrial Research (CSIR), Government of India, New Delhi, for the award of a research fellowship.

References

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