2,2,2-Tribromo-N-(3-methyl­phen­yl)acetamide

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

doi:10.1107/S160053680905048X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3242

doi:10.1107/S160053680905048X

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2,2,2-Tribromo-N-(3-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 November 2009; accepted 24 November 2009; online 28 November 2009)

The asymmetric unit of the title compound, C₉H₈Br₃NO, contains two independent molecules. The conformation of the N—H bond is anti to the 3-methyl substituent in the benzene ring in each molecule. The structure shows both intramolecular N—H⋯Br and intermolecular N—H⋯O hydrogen bonding, the latter leading to the formation of helical supramolecular chains along the b axis.

Related literature

For preparation of the compound, see: Gowda et al. (2003 ). For our study of the effect of ring and side-chain substituents on the solid-state structures of N-aromatic amides, see: Gowda et al. (2007a ,b , 2009 ). For the structures of other amides, see: Brown (1966 ).

Experimental

Crystal data

C₉H₈Br₃NO
M_r = 385.89
Monoclinic, P 2₁ /n
a = 11.360 (1) Å
b = 10.280 (1) Å
c = 20.298 (3) Å
β = 100.23 (1)°
V = 2332.7 (5) Å³
Z = 8
Cu Kα radiation
μ = 12.58 mm⁻¹
T = 299 K
0.28 × 0.13 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.127, T_max = 0.433
4358 measured reflections
4147 independent reflections
2939 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.080
wR(F²) = 0.249
S = 1.04
4147 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 1.60 e Å⁻³
Δρ_min = −1.66 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.86	2.21	3.005 (11)	153
N1—H1N⋯Br1	0.86	2.60	3.068 (8)	115
N2—H2N⋯O1ⁱⁱ	0.86	2.11	2.886 (11)	150
N2—H2N⋯Br6	0.86	2.61	3.100 (8)	117
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -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/S160053680905048X/tk2583sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680905048X/tk2583Isup2.hkl

checkCIF report

Comment top

As part of a study of the effect of the ring and the side-chain substituents on the solid-state structures of N-aromatic amides (Gowda et al., 2007a, b, 2009), in the present work, the structure of N-(3-methylphenyl)2,2,2-tribromoacetamide (I) has been determined (Fig. 1). The asymmetric unit of the structure contains two independent molecules. The conformation of the N—H bond is anti to the 3-methyl substituent in the benzene ring in each molecule, similar to that observed in N-(3-methylphenyl)2,2,2-trichloroacetamide (Gowda et al., 2007a) and N-(3-methylphenyl)2,2,2-trimethylacetamide (Gowda et al., 2007b). Further, 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 N-(phenyl)2,2,2-tribromoacetamide (Gowda et al., 2009) and other amides (Brown, 1966; Gowda et al., 2007a,b). The structure of (I) shows both the intramolecular N—H···Br and intermolecular N—H···O hydrogen bonding, Table 1. The packing diagram showing the hydrogen bonds (Table 1) and the supramolecular chains parallel to the b axis is shown in Fig. 2.

Related literature top

For preparation of the compound, see: Gowda et al. (2003). For our study of the effect of ring and side-chain substituents on the solid-state structures of N-aromatic amides, see: Gowda et al. (2007a,b, 2009). For the structures of other amides, see: Brown (1966).

Experimental top

The title compound was prepared from m-toluidine, tribromoacetic acid and phosphorylchloride according to the literature method (Gowda et al., 2003). Single crystals of (I) were obtained by the slow evaporation of its petroleum ether solution 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 structures of the two independent molecules of (I), showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Molecular packing in (I) with hydrogen bonds shown as dashed lines.

2,2,2-Tribromo-N-(3-methylphenyl)acetamide top

Crystal data top

C₉H₈Br₃NO	F(000) = 1456
M_r = 385.89	D_x = 2.198 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 11.360 (1) Å	θ = 4.9–20.6°
b = 10.280 (1) Å	µ = 12.58 mm⁻¹
c = 20.298 (3) Å	T = 299 K
β = 100.23 (1)°	Rod, colourless
V = 2332.7 (5) Å³	0.28 × 0.13 × 0.08 mm
Z = 8

Data collection top

Enraf–Nonius CAD-4 diffractometer	2939 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.059
Graphite monochromator	θ_max = 67.0°, θ_min = 4.2°
ω/2θ scans	h = −13→1
Absorption correction: ψ scan (North et al., 1968)	k = −12→0
T_min = 0.127, T_max = 0.433	l = −23→24
4358 measured reflections	3 standard reflections every 120 min
4147 independent reflections	intensity decay: 1.0%

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.249	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1741P)² + 2.28P] where P = (F_o² + 2F_c²)/3
4147 reflections	(Δ/σ)_max < 0.001
255 parameters	Δρ_max = 1.60 e Å⁻³
0 restraints	Δρ_min = −1.66 e Å⁻³

Crystal data top

C₉H₈Br₃NO	V = 2332.7 (5) Å³
M_r = 385.89	Z = 8
Monoclinic, P2₁/n	Cu Kα radiation
a = 11.360 (1) Å	µ = 12.58 mm⁻¹
b = 10.280 (1) Å	T = 299 K
c = 20.298 (3) Å	0.28 × 0.13 × 0.08 mm
β = 100.23 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2939 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.059
T_min = 0.127, T_max = 0.433	3 standard reflections every 120 min
4358 measured reflections	intensity decay: 1.0%
4147 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.080	0 restraints
wR(F²) = 0.249	H-atom parameters constrained
S = 1.04	Δρ_max = 1.60 e Å⁻³
4147 reflections	Δρ_min = −1.66 e Å⁻³
255 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
C1	0.6706 (9)	0.5084 (11)	−0.0373 (5)	0.042 (2)
C2	0.6595 (10)	0.4132 (11)	−0.0870 (5)	0.049 (3)
H2	0.7156	0.3465	−0.0832	0.059*
C3	0.5676 (11)	0.4153 (13)	−0.1414 (6)	0.059 (3)
C4	0.4854 (11)	0.5134 (15)	−0.1451 (7)	0.068 (3)
H4	0.4246	0.5196	−0.1822	0.082*
C5	0.4922 (13)	0.6036 (15)	−0.0939 (8)	0.078 (4)
H5	0.4324	0.6660	−0.0959	0.094*
C6	0.5834 (11)	0.6036 (12)	−0.0409 (7)	0.060 (3)
H6	0.5874	0.6663	−0.0076	0.072*
C7	0.8238 (9)	0.4032 (9)	0.0454 (5)	0.038 (2)
C8	0.9316 (9)	0.4273 (9)	0.1025 (5)	0.041 (2)
C9	0.5614 (13)	0.3160 (14)	−0.1948 (6)	0.068 (4)
H9A	0.5043	0.2503	−0.1886	0.082*
H9B	0.6387	0.2768	−0.1928	0.082*
H9C	0.5373	0.3565	−0.2377	0.082*
Br1	1.01398 (11)	0.58885 (12)	0.09396 (6)	0.0534 (4)
Br2	0.86902 (12)	0.42753 (12)	0.18531 (5)	0.0544 (4)
Br3	1.04582 (12)	0.28886 (14)	0.10312 (7)	0.0645 (4)
N1	0.7674 (7)	0.5085 (8)	0.0170 (4)	0.0396 (18)
H1N	0.7923	0.5829	0.0332	0.047*
O1	0.7944 (8)	0.2926 (7)	0.0314 (4)	0.055 (2)
C10	0.1952 (9)	−0.0100 (10)	0.0500 (5)	0.041 (2)
C11	0.2737 (10)	0.0681 (10)	0.0959 (5)	0.047 (2)
H11	0.3299	0.1209	0.0808	0.056*
C12	0.2665 (13)	0.0654 (12)	0.1619 (5)	0.060 (3)
C13	0.1874 (14)	−0.0199 (13)	0.1849 (6)	0.070 (4)
H13	0.1880	−0.0289	0.2305	0.084*
C14	0.1082 (14)	−0.0910 (12)	0.1392 (7)	0.068 (4)
H14	0.0501	−0.1408	0.1543	0.082*
C15	0.1128 (12)	−0.0905 (11)	0.0720 (6)	0.056 (3)
H15	0.0619	−0.1428	0.0422	0.067*
C16	0.2210 (9)	0.0901 (9)	−0.0539 (5)	0.041 (2)
C17	0.2661 (11)	0.0687 (11)	−0.1209 (6)	0.051 (3)
C18	0.3472 (14)	0.1501 (18)	0.2107 (7)	0.084 (5)
H18A	0.3064	0.2295	0.2174	0.101*
H18B	0.4184	0.1696	0.1933	0.101*
H18C	0.3682	0.1052	0.2526	0.101*
Br4	0.22259 (14)	0.21315 (14)	−0.17949 (7)	0.0697 (5)
Br5	0.44004 (14)	0.05889 (19)	−0.09624 (9)	0.0877 (6)
Br6	0.21012 (18)	−0.08796 (14)	−0.16568 (7)	0.0792 (5)
N2	0.2067 (9)	−0.0130 (8)	−0.0181 (4)	0.047 (2)
H2N	0.2041	−0.0876	−0.0375	0.056*
O2	0.2111 (8)	0.2020 (7)	−0.0359 (4)	0.0539 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.043 (5)	0.053 (6)	0.031 (5)	0.005 (5)	0.007 (4)	0.005 (4)
C2	0.041 (5)	0.068 (7)	0.035 (5)	0.000 (5)	0.002 (4)	0.003 (5)
C3	0.052 (6)	0.083 (9)	0.041 (6)	−0.015 (6)	0.009 (5)	0.008 (6)
C4	0.051 (7)	0.089 (10)	0.059 (8)	−0.008 (7)	−0.006 (6)	0.007 (7)
C5	0.064 (8)	0.084 (10)	0.083 (11)	0.020 (8)	0.000 (7)	0.020 (8)
C6	0.056 (7)	0.052 (7)	0.070 (8)	−0.010 (5)	0.007 (6)	0.005 (6)
C7	0.046 (5)	0.037 (5)	0.031 (5)	0.005 (4)	0.007 (4)	0.004 (4)
C8	0.048 (6)	0.043 (5)	0.030 (5)	0.001 (4)	0.003 (4)	0.002 (4)
C9	0.083 (9)	0.087 (9)	0.033 (6)	−0.020 (7)	0.007 (6)	−0.004 (6)
Br1	0.0538 (7)	0.0568 (7)	0.0478 (7)	−0.0096 (5)	0.0043 (5)	−0.0019 (5)
Br2	0.0668 (8)	0.0680 (8)	0.0295 (6)	0.0008 (6)	0.0110 (5)	0.0026 (5)
Br3	0.0608 (8)	0.0645 (8)	0.0660 (8)	0.0231 (6)	0.0057 (6)	0.0021 (6)
N1	0.036 (4)	0.035 (4)	0.045 (5)	−0.001 (3)	0.000 (3)	0.002 (3)
O1	0.078 (5)	0.037 (4)	0.043 (4)	−0.003 (4)	−0.009 (4)	−0.003 (3)
C10	0.057 (6)	0.036 (5)	0.031 (5)	0.013 (4)	0.010 (4)	0.003 (4)
C11	0.055 (6)	0.052 (6)	0.033 (5)	0.014 (5)	0.005 (4)	0.002 (4)
C12	0.080 (8)	0.070 (8)	0.026 (5)	0.020 (6)	−0.004 (5)	−0.004 (5)
C13	0.110 (11)	0.067 (8)	0.037 (6)	0.019 (8)	0.029 (7)	−0.001 (6)
C14	0.108 (11)	0.050 (7)	0.059 (8)	−0.007 (7)	0.051 (8)	0.004 (5)
C15	0.077 (8)	0.048 (6)	0.046 (6)	−0.003 (6)	0.024 (6)	−0.010 (5)
C16	0.052 (6)	0.042 (5)	0.028 (5)	0.000 (4)	0.006 (4)	−0.007 (4)
C17	0.058 (7)	0.055 (6)	0.043 (6)	0.001 (5)	0.016 (5)	0.005 (5)
C18	0.086 (10)	0.118 (13)	0.042 (7)	0.010 (9)	−0.007 (7)	−0.016 (8)
Br4	0.0915 (10)	0.0705 (9)	0.0531 (8)	0.0183 (7)	0.0289 (7)	0.0263 (6)
Br5	0.0563 (8)	0.1225 (15)	0.0868 (12)	0.0133 (8)	0.0192 (8)	0.0250 (10)
Br6	0.1327 (15)	0.0674 (9)	0.0405 (7)	−0.0189 (8)	0.0231 (8)	−0.0114 (6)
N2	0.072 (6)	0.035 (4)	0.035 (4)	−0.001 (4)	0.015 (4)	−0.003 (3)
O2	0.079 (5)	0.033 (4)	0.050 (4)	0.003 (4)	0.013 (4)	0.002 (3)

Geometric parameters (Å, º) top

C1—C6	1.385 (16)	C10—C15	1.382 (16)
C1—C2	1.394 (15)	C10—N2	1.411 (12)
C1—N1	1.412 (12)	C10—C11	1.419 (15)
C2—C3	1.379 (16)	C11—C12	1.357 (15)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.367 (19)	C12—C13	1.39 (2)
C3—C9	1.482 (17)	C12—C18	1.503 (18)
C4—C5	1.38 (2)	C13—C14	1.38 (2)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.354 (18)	C14—C15	1.373 (16)
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	C15—H15	0.9300
C7—O1	1.205 (12)	C16—O2	1.218 (12)
C7—N1	1.336 (12)	C16—N2	1.311 (13)
C7—C8	1.548 (14)	C16—C17	1.553 (14)
C8—Br3	1.925 (10)	C17—Br6	1.902 (12)
C8—Br1	1.929 (10)	C17—Br4	1.912 (11)
C8—Br2	1.938 (10)	C17—Br5	1.953 (12)
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	0.8600	N2—H2N	0.8600

C6—C1—C2	119.0 (10)	C15—C10—N2	119.4 (9)
C6—C1—N1	119.4 (10)	C15—C10—C11	120.6 (10)
C2—C1—N1	121.5 (9)	N2—C10—C11	119.9 (10)
C3—C2—C1	121.8 (11)	C12—C11—C10	119.7 (12)
C3—C2—H2	119.1	C12—C11—H11	120.1
C1—C2—H2	119.1	C10—C11—H11	120.1
C4—C3—C2	117.9 (12)	C11—C12—C13	119.9 (12)
C4—C3—C9	121.7 (12)	C11—C12—C18	120.2 (14)
C2—C3—C9	120.4 (12)	C13—C12—C18	119.8 (12)
C3—C4—C5	120.5 (12)	C14—C13—C12	119.3 (11)
C3—C4—H4	119.8	C14—C13—H13	120.3
C5—C4—H4	119.8	C12—C13—H13	120.3
C6—C5—C4	121.9 (13)	C15—C14—C13	122.0 (12)
C6—C5—H5	119.1	C15—C14—H14	119.0
C4—C5—H5	119.1	C13—C14—H14	119.0
C5—C6—C1	118.8 (13)	C14—C15—C10	118.1 (11)
C5—C6—H6	120.6	C14—C15—H15	120.9
C1—C6—H6	120.6	C10—C15—H15	120.9
O1—C7—N1	124.8 (9)	O2—C16—N2	124.8 (9)
O1—C7—C8	118.5 (8)	O2—C16—C17	117.3 (9)
N1—C7—C8	116.6 (8)	N2—C16—C17	117.6 (9)
C7—C8—Br3	109.2 (6)	C16—C17—Br6	113.8 (7)
C7—C8—Br1	113.8 (6)	C16—C17—Br4	110.2 (7)
Br3—C8—Br1	107.4 (5)	Br6—C17—Br4	109.5 (6)
C7—C8—Br2	106.6 (7)	C16—C17—Br5	105.0 (7)
Br3—C8—Br2	110.2 (5)	Br6—C17—Br5	108.4 (6)
Br1—C8—Br2	109.6 (5)	Br4—C17—Br5	109.7 (6)
C3—C9—H9A	109.5	C12—C18—H18A	109.5
C3—C9—H9B	109.5	C12—C18—H18B	109.5
H9A—C9—H9B	109.5	H18A—C18—H18B	109.5
C3—C9—H9C	109.5	C12—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	125.7 (9)	C16—N2—C10	124.5 (8)
C7—N1—H1N	117.1	C16—N2—H2N	117.7
C1—N1—H1N	117.1	C10—N2—H2N	117.7

C6—C1—C2—C3	3.6 (17)	C15—C10—C11—C12	−1.1 (16)
N1—C1—C2—C3	−177.6 (10)	N2—C10—C11—C12	−176.5 (10)
C1—C2—C3—C4	−1.0 (17)	C10—C11—C12—C13	4.1 (17)
C1—C2—C3—C9	177.3 (10)	C10—C11—C12—C18	−178.5 (11)
C2—C3—C4—C5	−3 (2)	C11—C12—C13—C14	−7 (2)
C9—C3—C4—C5	178.9 (12)	C18—C12—C13—C14	175.8 (13)
C3—C4—C5—C6	4 (2)	C12—C13—C14—C15	7 (2)
C4—C5—C6—C1	−2 (2)	C13—C14—C15—C10	−4 (2)
C2—C1—C6—C5	−2.3 (18)	N2—C10—C15—C14	176.3 (11)
N1—C1—C6—C5	178.9 (11)	C11—C10—C15—C14	0.9 (17)
O1—C7—C8—Br3	33.1 (12)	O2—C16—C17—Br6	−151.8 (9)
N1—C7—C8—Br3	−149.3 (7)	N2—C16—C17—Br6	34.1 (13)
O1—C7—C8—Br1	153.1 (8)	O2—C16—C17—Br4	−28.4 (13)
N1—C7—C8—Br1	−29.2 (11)	N2—C16—C17—Br4	157.5 (8)
O1—C7—C8—Br2	−86.0 (10)	O2—C16—C17—Br5	89.7 (10)
N1—C7—C8—Br2	91.6 (9)	N2—C16—C17—Br5	−84.4 (10)
O1—C7—N1—C1	−5.2 (17)	O2—C16—N2—C10	−9.8 (18)
C8—C7—N1—C1	177.3 (9)	C17—C16—N2—C10	163.8 (10)
C6—C1—N1—C7	146.8 (11)	C15—C10—N2—C16	139.2 (11)
C2—C1—N1—C7	−32.0 (15)	C11—C10—N2—C16	−45.4 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.86	2.21	3.005 (11)	153
N1—H1N···Br1	0.86	2.60	3.068 (8)	115
N2—H2N···O1ⁱⁱ	0.86	2.11	2.886 (11)	150
N2—H2N···Br6	0.86	2.61	3.100 (8)	117

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

Experimental details

Crystal data
Chemical formula	C₉H₈Br₃NO
M_r	385.89
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	299
a, b, c (Å)	11.360 (1), 10.280 (1), 20.298 (3)
β (°)	100.23 (1)
V (Å³)	2332.7 (5)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	12.58
Crystal size (mm)	0.28 × 0.13 × 0.08

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.127, 0.433
No. of measured, independent and observed [I > 2σ(I)] reflections	4358, 4147, 2939
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.249, 1.04
No. of reflections	4147
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.60, −1.66

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···O2ⁱ	0.86	2.21	3.005 (11)	153
N1—H1N···Br1	0.86	2.60	3.068 (8)	115
N2—H2N···O1ⁱⁱ	0.86	2.11	2.886 (11)	150
N2—H2N···Br6	0.86	2.61	3.100 (8)	117

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

References

Brown, C. J. (1966). Acta Cryst. 21, 442–445. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Enraf–Nonius (1996). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2009). Acta Cryst. E65, o2226. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Kozisek, J., Svoboda, I. & Fuess, H. (2007a). Z. Naturforsch. Teil A, 62, 91–100. CAS Google Scholar
Gowda, B. T., Kozisek, J., Tokarčík, M. & Fuess, H. (2007b). Acta Cryst. E63, o2073–o2074. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Usha, K. M. & Jayalakshmi, K. L. (2003). Z. Naturforsch. Teil A, 58, 801–806. CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science 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
Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany. Google Scholar

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Volume 65| Part 12| December 2009| Page o3242

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