2,2,2-Tribromo-N-(4-methyl­phen­yl)acetamide

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

doi:10.1107/S1600536810009177

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o849

doi:10.1107/S1600536810009177

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2,2,2-Tribromo-N-(4-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 7 March 2010; accepted 10 March 2010; online 17 March 2010)

The asymmetric unit of the title compound, C₉H₈Br₃NO, contains two independent molecules which differ in the orientation of the tribromo group. A weak intramolecular N—H⋯Br hydrogen bond is observed in each molecule. In the crystal, the independent molecules are linked into chains along the b axis by intermolecular N—H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C₉H₈Br₃NO
M_r = 385.89
Monoclinic, P 2₁ /c
a = 9.6926 (6) Å
b = 20.531 (1) Å
c = 11.8139 (8) Å
β = 102.664 (7)°
V = 2293.8 (2) Å³
Z = 8
Mo Kα radiation
μ = 10.52 mm⁻¹
T = 299 K
0.48 × 0.40 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.081, T_max = 0.145
14714 measured reflections
4121 independent reflections
3375 reflections with I > 2σ(I)
R_int = 0.089

Refinement

R[F² > 2σ(F²)] = 0.082
wR(F²) = 0.151
S = 1.28
4121 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 1.34 e Å⁻³
Δρ_min = −0.88 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2	0.86	2.27	3.078 (10)	156
N1—H1N⋯Br2	0.86	2.61	3.111 (8)	118
N2—H2N⋯O1ⁱ	0.86	2.27	3.032 (10)	148
N2—H2N⋯Br4	0.86	2.56	3.051 (9)	118
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; 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/S1600536810009177/ci5053sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810009177/ci5053Isup2.hkl

checkCIF report

Comment top

As part of a study of the effect of the ring and the side chain substituents on solid state structures of N-aromatic amides (Gowda et al., 2009a,b,c), in the present work, the crytsal structure of 2,2,2-tribromo-N-(4-methylphenyl)acetamide has been determined (Fig.1). The asymmetric unit of the structure contains two independent molecules, which differ in the orientation of the tribromo group as is evident from either the C-N-CO-CBr3 or N-CO-C-Br torsional angles. The conformations of the N—H bonds in both molecules are anti to the C═O bonds in the side chains, similar to those observed in 2,2,2-tribromo-N-(3-methylphenyl)acetamide (Gowda et al., 2009a), 2,2,2-tribromo-N-(phenyl)acetamide (Gowda et al., 2009b), 2,2,2-tribromo-N-(4-chlorophenyl)acetamide (Gowda et al., 2009c) and other amides (Brown, 1966). The structure of the title compound shows both the intramolecular N—H···Br and intermolecular N—H···O hydrogen bonding.

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

Experimental top

The title compound was prepared from p-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: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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. The asymmetric unit 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 radii.
	Fig. 2. Molecular packing in the crystal structure of the title compound, with hydrogen bonds shown as dashed lines.

2,2,2-Tribromo-N-(4-methylphenyl)acetamide top

Crystal data top

C₉H₈Br₃NO	F(000) = 1456
M_r = 385.89	D_x = 2.235 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5162 reflections
a = 9.6926 (6) Å	θ = 2.7–27.8°
b = 20.531 (1) Å	µ = 10.52 mm⁻¹
c = 11.8139 (8) Å	T = 299 K
β = 102.664 (7)°	Prism, colourless
V = 2293.8 (2) Å³	0.48 × 0.40 × 0.30 mm
Z = 8

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	4121 independent reflections
Radiation source: fine-focus sealed tube	3375 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.089
Rotation method data acquisition using ω and ϕ scans.	θ_max = 25.4°, θ_min = 4.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→11
T_min = 0.081, T_max = 0.145	k = −21→24
14714 measured reflections	l = −13→14

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)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.28	w = 1/[σ²(F_o²) + (0.P)² + 26.8682P] where P = (F_o² + 2F_c²)/3
4121 reflections	(Δ/σ)_max = 0.001
255 parameters	Δρ_max = 1.34 e Å⁻³
0 restraints	Δρ_min = −0.88 e Å⁻³

Crystal data top

C₉H₈Br₃NO	V = 2293.8 (2) Å³
M_r = 385.89	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.6926 (6) Å	µ = 10.52 mm⁻¹
b = 20.531 (1) Å	T = 299 K
c = 11.8139 (8) Å	0.48 × 0.40 × 0.30 mm
β = 102.664 (7)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	4121 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	3375 reflections with I > 2σ(I)
T_min = 0.081, T_max = 0.145	R_int = 0.089
14714 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.28	w = 1/[σ²(F_o²) + (0.P)² + 26.8682P] where P = (F_o² + 2F_c²)/3
4121 reflections	Δρ_max = 1.34 e Å⁻³
255 parameters	Δρ_min = −0.88 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	0.7165 (11)	0.2486 (4)	0.6954 (9)	0.029 (2)
C2	0.7414 (11)	0.1962 (5)	0.6292 (10)	0.035 (3)
H2	0.6948	0.1569	0.6335	0.043*
C3	0.8348 (12)	0.2017 (5)	0.5568 (11)	0.043 (3)
H3	0.8516	0.1658	0.5136	0.051*
C4	0.9039 (11)	0.2598 (5)	0.5475 (9)	0.034 (2)
C5	0.8797 (12)	0.3110 (5)	0.6175 (10)	0.039 (3)
H5	0.9279	0.3500	0.6149	0.047*
C6	0.7875 (12)	0.3065 (5)	0.6901 (10)	0.037 (3)
H6	0.7730	0.3419	0.7353	0.044*
C7	0.5389 (11)	0.2876 (4)	0.7992 (9)	0.028 (2)
C8	0.4213 (11)	0.2643 (4)	0.8592 (9)	0.029 (2)
C9	1.0009 (12)	0.2673 (6)	0.4652 (10)	0.043 (3)
H9A	0.9464	0.2667	0.3869	0.052*
H9B	1.0675	0.2320	0.4762	0.052*
H9C	1.0507	0.3079	0.4800	0.052*
Br1	0.37301 (14)	0.33225 (5)	0.95617 (12)	0.0480 (4)
Br2	0.46539 (15)	0.18686 (5)	0.95318 (12)	0.0510 (4)
Br3	0.25450 (14)	0.24690 (6)	0.73598 (12)	0.0531 (4)
N1	0.6157 (9)	0.2404 (4)	0.7652 (8)	0.033 (2)
H1N	0.6029	0.2015	0.7877	0.039*
O1	0.5509 (8)	0.3449 (3)	0.7822 (7)	0.042 (2)
C10	0.3798 (10)	0.0087 (4)	0.6530 (9)	0.025 (2)
C11	0.3488 (11)	−0.0253 (5)	0.5503 (10)	0.036 (3)
H11	0.4045	−0.0606	0.5390	0.044*
C12	0.2340 (11)	−0.0068 (5)	0.4633 (10)	0.034 (3)
H12	0.2144	−0.0297	0.3937	0.041*
C13	0.1478 (10)	0.0452 (5)	0.4785 (9)	0.029 (2)
C14	0.1792 (12)	0.0765 (5)	0.5829 (11)	0.038 (3)
H14	0.1220	0.1108	0.5960	0.046*
C15	0.2935 (12)	0.0590 (5)	0.6701 (10)	0.035 (3)
H15	0.3117	0.0813	0.7403	0.042*
C16	0.5967 (10)	0.0331 (5)	0.7916 (10)	0.030 (2)
C17	0.7240 (12)	0.0074 (5)	0.8818 (10)	0.036 (3)
C18	0.0294 (13)	0.0685 (5)	0.3837 (10)	0.042 (3)
H18A	0.0032	0.0346	0.3270	0.050*
H18B	0.0595	0.1062	0.3475	0.050*
H18C	−0.0504	0.0795	0.4157	0.050*
Br4	0.75931 (14)	−0.08465 (6)	0.87190 (14)	0.0582 (4)
Br5	0.89309 (14)	0.05436 (7)	0.86845 (12)	0.0540 (4)
Br6	0.69036 (17)	0.02579 (8)	1.03563 (12)	0.0661 (4)
N2	0.5023 (9)	−0.0097 (4)	0.7398 (8)	0.032 (2)
H2N	0.5144	−0.0501	0.7586	0.038*
O2	0.5901 (9)	0.0912 (3)	0.7746 (8)	0.049 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.024 (5)	0.027 (5)	0.037 (7)	0.003 (4)	0.006 (5)	0.004 (4)
C2	0.032 (6)	0.025 (5)	0.049 (8)	0.002 (4)	0.007 (6)	−0.001 (5)
C3	0.039 (7)	0.034 (6)	0.057 (9)	0.005 (5)	0.015 (6)	−0.011 (5)
C4	0.031 (6)	0.045 (6)	0.020 (6)	0.008 (5)	−0.004 (5)	0.007 (5)
C5	0.032 (6)	0.036 (6)	0.049 (8)	−0.008 (5)	0.006 (6)	−0.003 (5)
C6	0.035 (6)	0.033 (5)	0.043 (7)	−0.006 (5)	0.008 (6)	−0.009 (5)
C7	0.030 (6)	0.027 (5)	0.028 (6)	0.001 (4)	0.006 (5)	0.001 (4)
C8	0.030 (6)	0.022 (5)	0.029 (6)	0.005 (4)	−0.008 (5)	−0.002 (4)
C9	0.035 (7)	0.055 (7)	0.035 (7)	−0.003 (6)	−0.004 (6)	−0.009 (6)
Br1	0.0487 (7)	0.0402 (6)	0.0610 (9)	−0.0018 (5)	0.0251 (7)	−0.0155 (6)
Br2	0.0660 (9)	0.0386 (6)	0.0484 (8)	0.0034 (6)	0.0128 (7)	0.0101 (6)
Br3	0.0423 (7)	0.0586 (8)	0.0496 (9)	−0.0124 (6)	−0.0086 (6)	−0.0035 (6)
N1	0.035 (5)	0.015 (4)	0.049 (6)	0.000 (4)	0.009 (5)	−0.002 (4)
O1	0.042 (5)	0.021 (4)	0.064 (6)	0.004 (3)	0.017 (4)	0.001 (3)
C10	0.024 (5)	0.022 (5)	0.027 (6)	−0.003 (4)	0.001 (5)	0.004 (4)
C11	0.027 (6)	0.030 (5)	0.051 (8)	0.001 (5)	0.007 (6)	−0.002 (5)
C12	0.032 (6)	0.037 (6)	0.032 (7)	0.000 (5)	0.004 (5)	−0.003 (5)
C13	0.024 (5)	0.028 (5)	0.034 (7)	0.000 (4)	0.007 (5)	0.008 (5)
C14	0.035 (6)	0.028 (5)	0.053 (8)	0.007 (5)	0.014 (6)	0.003 (5)
C15	0.048 (7)	0.026 (5)	0.030 (7)	−0.001 (5)	0.002 (6)	−0.010 (5)
C16	0.023 (5)	0.026 (5)	0.044 (7)	−0.001 (4)	0.012 (5)	−0.003 (5)
C17	0.034 (6)	0.026 (5)	0.044 (7)	−0.009 (5)	0.001 (6)	−0.004 (5)
C18	0.045 (7)	0.046 (6)	0.031 (7)	0.006 (6)	0.002 (6)	0.009 (5)
Br4	0.0472 (8)	0.0352 (6)	0.0788 (11)	0.0055 (5)	−0.0149 (7)	0.0032 (6)
Br5	0.0393 (7)	0.0677 (8)	0.0523 (9)	−0.0199 (6)	0.0043 (6)	−0.0008 (7)
Br6	0.0644 (10)	0.0966 (11)	0.0391 (8)	−0.0102 (8)	0.0150 (7)	−0.0027 (7)
N2	0.033 (5)	0.018 (4)	0.040 (6)	−0.002 (4)	−0.001 (4)	−0.001 (4)
O2	0.044 (5)	0.022 (4)	0.076 (7)	−0.008 (3)	−0.001 (5)	0.005 (4)

Geometric parameters (Å, º) top

C1—C2	1.383 (14)	C10—C15	1.371 (13)
C1—C6	1.382 (13)	C10—C11	1.374 (14)
C1—N1	1.420 (12)	C10—N2	1.439 (13)
C2—C3	1.380 (15)	C11—C12	1.392 (15)
C2—H2	0.93	C11—H11	0.93
C3—C4	1.384 (15)	C12—C13	1.392 (13)
C3—H3	0.93	C12—H12	0.93
C4—C5	1.389 (14)	C13—C14	1.366 (15)
C4—C9	1.501 (15)	C13—C18	1.495 (15)
C5—C6	1.371 (15)	C14—C15	1.384 (16)
C5—H5	0.93	C14—H14	0.93
C6—H6	0.93	C15—H15	0.93
C7—O1	1.201 (11)	C16—O2	1.209 (11)
C7—N1	1.337 (12)	C16—N2	1.318 (13)
C7—C8	1.545 (14)	C16—C17	1.536 (15)
C8—Br1	1.927 (9)	C17—Br4	1.928 (10)
C8—Br2	1.932 (9)	C17—Br5	1.938 (10)
C8—Br3	1.957 (10)	C17—Br6	1.953 (11)
C9—H9A	0.96	C18—H18A	0.96
C9—H9B	0.96	C18—H18B	0.96
C9—H9C	0.96	C18—H18C	0.96
N1—H1N	0.86	N2—H2N	0.86

C2—C1—C6	119.6 (9)	C15—C10—C11	119.3 (10)
C2—C1—N1	117.7 (8)	C15—C10—N2	121.8 (9)
C6—C1—N1	122.8 (9)	C11—C10—N2	118.8 (9)
C3—C2—C1	120.5 (9)	C10—C11—C12	119.9 (10)
C3—C2—H2	119.8	C10—C11—H11	120.1
C1—C2—H2	119.8	C12—C11—H11	120.1
C2—C3—C4	120.9 (10)	C13—C12—C11	121.3 (10)
C2—C3—H3	119.5	C13—C12—H12	119.4
C4—C3—H3	119.5	C11—C12—H12	119.4
C3—C4—C5	117.2 (10)	C14—C13—C12	117.2 (10)
C3—C4—C9	121.5 (10)	C14—C13—C18	120.6 (9)
C5—C4—C9	121.3 (10)	C12—C13—C18	122.2 (10)
C6—C5—C4	122.7 (10)	C13—C14—C15	122.2 (10)
C6—C5—H5	118.7	C13—C14—H14	118.9
C4—C5—H5	118.7	C15—C14—H14	118.9
C5—C6—C1	119.1 (10)	C10—C15—C14	120.1 (10)
C5—C6—H6	120.5	C10—C15—H15	120.0
C1—C6—H6	120.5	C14—C15—H15	120.0
O1—C7—N1	125.4 (9)	O2—C16—N2	125.0 (11)
O1—C7—C8	119.2 (8)	O2—C16—C17	117.4 (9)
N1—C7—C8	115.3 (8)	N2—C16—C17	117.6 (8)
C7—C8—Br1	110.4 (6)	C16—C17—Br4	114.9 (7)
C7—C8—Br2	115.2 (6)	C16—C17—Br5	109.7 (7)
Br1—C8—Br2	107.8 (5)	Br4—C17—Br5	108.5 (5)
C7—C8—Br3	106.7 (7)	C16—C17—Br6	107.9 (7)
Br1—C8—Br3	107.8 (5)	Br4—C17—Br6	108.3 (5)
Br2—C8—Br3	108.7 (5)	Br5—C17—Br6	107.2 (5)
C4—C9—H9A	109.5	C13—C18—H18A	109.5
C4—C9—H9B	109.5	C13—C18—H18B	109.5
H9A—C9—H9B	109.5	H18A—C18—H18B	109.5
C4—C9—H9C	109.5	C13—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	126.0 (8)	C16—N2—C10	122.4 (8)
C7—N1—H1N	117.0	C16—N2—H2N	118.8
C1—N1—H1N	117.0	C10—N2—H2N	118.8

C6—C1—C2—C3	−1.0 (17)	C15—C10—C11—C12	2.5 (14)
N1—C1—C2—C3	178.0 (10)	N2—C10—C11—C12	−177.6 (9)
C1—C2—C3—C4	−1.0 (18)	C10—C11—C12—C13	−0.8 (15)
C2—C3—C4—C5	2.7 (17)	C11—C12—C13—C14	−1.2 (14)
C2—C3—C4—C9	−177.3 (11)	C11—C12—C13—C18	176.1 (10)
C3—C4—C5—C6	−2.6 (17)	C12—C13—C14—C15	1.5 (15)
C9—C4—C5—C6	177.4 (11)	C18—C13—C14—C15	−175.8 (10)
C4—C5—C6—C1	0.7 (18)	C11—C10—C15—C14	−2.2 (15)
C2—C1—C6—C5	1.2 (17)	N2—C10—C15—C14	177.9 (9)
N1—C1—C6—C5	−177.8 (11)	C13—C14—C15—C10	0.1 (16)
O1—C7—C8—Br1	−26.3 (12)	O2—C16—C17—Br4	−162.1 (8)
N1—C7—C8—Br1	156.8 (8)	N2—C16—C17—Br4	18.7 (12)
O1—C7—C8—Br2	−148.7 (9)	O2—C16—C17—Br5	−39.5 (12)
N1—C7—C8—Br2	34.4 (12)	N2—C16—C17—Br5	141.3 (8)
O1—C7—C8—Br3	90.6 (10)	O2—C16—C17—Br6	77.0 (10)
N1—C7—C8—Br3	−86.3 (9)	N2—C16—C17—Br6	−102.2 (9)
O1—C7—N1—C1	−5.5 (18)	O2—C16—N2—C10	1.6 (16)
C8—C7—N1—C1	171.2 (10)	C17—C16—N2—C10	−179.3 (9)
C2—C1—N1—C7	−153.2 (11)	C15—C10—N2—C16	−49.1 (14)
C6—C1—N1—C7	25.8 (17)	C11—C10—N2—C16	130.9 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.86	2.27	3.078 (10)	156
N1—H1N···Br2	0.86	2.61	3.111 (8)	118
N2—H2N···O1ⁱ	0.86	2.27	3.032 (10)	148
N2—H2N···Br4	0.86	2.56	3.051 (9)	118

Symmetry code: (i) −x+1, y−1/2, −z+3/2.

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)	9.6926 (6), 20.531 (1), 11.8139 (8)
β (°)	102.664 (7)
V (Å³)	2293.8 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	10.52
Crystal size (mm)	0.48 × 0.40 × 0.30

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.081, 0.145
No. of measured, independent and observed [I > 2σ(I)] reflections	14714, 4121, 3375
R_int	0.089
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.082, 0.151, 1.28
No. of reflections	4121
No. of parameters	255
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.P)² + 26.8682P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.34, −0.88

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), 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	0.86	2.27	3.078 (10)	156
N1—H1N···Br2	0.86	2.61	3.111 (8)	118
N2—H2N···O1ⁱ	0.86	2.27	3.032 (10)	148
N2—H2N···Br4	0.86	2.56	3.051 (9)	118

Symmetry code: (i) −x+1, y−1/2, −z+3/2.

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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