1-Dibromo­methyl-4-meth­oxy-2-nitro­benzene

Fun, H.-K.; Goh, J.H.; Chandrakantha, B.; Isloor, A.M.

doi:10.1107/S1600536809031833

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Pages o2193-o2194

doi:10.1107/S1600536809031833

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1-Dibromomethyl-4-methoxy-2-nitrobenzene

Hoong-Kun Fun,^a ^*‡ Jia Hao Goh,^a B. Chandrakantha ^b and Arun M. Isloor ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bSyngene International Ltd, Biocon Park, Plot Nos. 2 & 3, Bommasandra 4th Phase, Jigani Link Road, Bangalore 560 100, India, and ^cDepartment of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
^*Correspondence e-mail: hkfun@usm.my

(Received 10 August 2009; accepted 12 August 2009; online 19 August 2009)

The asymmetric unit of the title compound, C₈H₇Br₂NO₃, comprises two crystallographically independent molecules (A and B). The nitro groups are twisted from the attached benzene rings, making dihedral angles of 39.26 (9) and 35.90 (9)° in molecules A and B, respectively. In each molecule, the dibromomethyl group is orientated in such a way that the two Br atoms are tilted away from the benzene ring. An interesting features of the crystal structure is the two short Br⋯Br interactions which, together with intermolecular C—H⋯O hydrogen bonds, link the molecules into an extended three-dimensional network. The crystal structure is further stabilized by weak C—H⋯π interactions.

Related literature

For general background to and applications of brominated organic compounds, see Augustine et al. (2007 ); Derdau et al. (2003 ); Khatuya (2001 ); Tyeklar et al. (1993 ). For related structures, see: Fun, Chantrapromma, Maity et al. (2009 ); Fun, Chantrapromma, Sujith et al. (2009 ); Yeap et al. (2008 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₈H₇Br₂NO₃
M_r = 324.97
Triclinic, $[P \overline 1]$
a = 7.9591 (1) Å
b = 11.1949 (2) Å
c = 12.2509 (2) Å
α = 106.285 (1)°
β = 99.691 (1)°
γ = 102.401 (1)°
V = 992.45 (3) Å³
Z = 4
Mo Kα radiation
μ = 8.15 mm⁻¹
T = 100 K
0.28 × 0.25 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.210, T_max = 0.311 (expected range = 0.147–0.218)
32659 measured reflections
8800 independent reflections
7332 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.066
S = 1.01
8800 reflections
261 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Selected interatomic distances (Å)

Br1A⋯Br2Bⁱ	3.5915 (3)
Br2A⋯Br1Bⁱⁱ	3.6279 (2)
Symmetry codes: (i) x+1, y+1, z; (ii) -x+1, -y+2, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7A—H7A⋯O2B	0.95 (2)	2.47 (2)	3.134 (2)	126.8 (17)
C8B—H8BA⋯O1Aⁱⁱⁱ	0.96	2.52	3.370 (2)	148
C8A—H8AA⋯Cg2^iv	0.96	2.95	3.839 (2)	155
Symmetry codes: (iii) x, y, z+1; (iv) -x+1, -y+1, -z. Cg2 is the centroid of the C1B–C6B benzene ring.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031833/wn2343sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809031833/wn2343Isup2.hkl

checkCIF report

Comment top

Brominated organic compounds are important synthetic intermediates and products in organic chemistry (Augustine et al., 2007). They are found in C-C coupling reactions, as precursors to organometallic species and in nucleophilic substitutions (Tyeklar et al., 1993). They are also used for the synthesis of useful pharmaceutical materials and agrochemicals (Derdau et al., 2003). However the use of molecular bromine as an electrophilic brominating reagent has several drawbacks arising from its toxic and corrosive nature and its high reactivity (Tyeklar et al., 1993). Alternative brominating reagents such as N-bromosuccinimide make for easier handling and result in improved selectivity (Khatuya, 2001).

In the asymmetric unit of the title compound, there are two crystallographically independent molecules, designated A and B (Fig. 1). In each molecule, the nitro group is twisted from the mean plane of the C1-C6 benzene ring, as shown by the dihedral angle formed between the mean plane through C5/N1/O2/O3 and the C1-C6 benzene ring of 39.26 (9)° in molecule A; the comparable angle is 35.90 (9)° for molecule B. Meanwhile, the dibromomethyl group is orientated in such a way that the two Br atoms are tilted away from the benzene ring. The bond lengths and angles are comparable to those found in related structures (Fun, Chantrapromma, Maity et al., 2009; Fun, Chantrapromma, Sujith et al., 2009; Yeap et al., 2008).

In the crystal structure (Fig. 2), the interesting features are the Br1A···Br2B and Br2A···Br1B short interactions (Table 1). Together with intermolecular C7A—H7A···O2B and C8B—H8BA···O1A hydrogen bonds (Table 2), they link the molecules into a three-dimensional extended network. The crystal structure is further stabilized by weak C8A—H8AA···Cg2 interactions (Table 2).

Related literature top

For general background to and applications of brominated organic compounds, see Augustine et al. (2007); Derdau et al. (2003); Khatuya (2001); Tyeklar et al. (1993). For related structures, see: Fun, Chantrapromma, Maity et al. (2009); Fun, Chantrapromma, Sujith et al. (2009); Yeap et al. (2008). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). Cg2 is the centroid of the C1B–C6B benzene ring.

Experimental top

Benzoyl peroxide (0.20 g, 10 %) and N-bromosuccinimide (6.38 g, 0.0358 mol) were added in portions to a solution of 4-methyl-2-nitroanisole (2.00 g, 0.0119 mol) in CCl₄ (20 ml). The reaction mixture was heated at 85 °C under a nitrogen atmosphere for 12 h. The reaction mass was cooled and filtered. The filtrate was concentrated to produce a crude product. The latter was recrystallized with hexane to afford the title compound as a colourless crystalline solid. The yield was 3.50 g, 92 %. M.p. 370–373 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. Three-dimensional extended network, viewed along the a axis. Intermolecular interactions are shown as dashed lines.

1-Dibromomethyl-4-methoxy-2-nitrobenzene top

Crystal data top

C₈H₇Br₂NO₃	Z = 4
M_r = 324.97	F(000) = 624
Triclinic, P1	D_x = 2.175 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9591 (1) Å	Cell parameters from 9885 reflections
b = 11.1949 (2) Å	θ = 2.2–35.1°
c = 12.2509 (2) Å	µ = 8.15 mm⁻¹
α = 106.285 (1)°	T = 100 K
β = 99.691 (1)°	Block, colourless
γ = 102.401 (1)°	0.28 × 0.25 × 0.19 mm
V = 992.45 (3) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	8800 independent reflections
Radiation source: fine-focus sealed tube	7332 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 35.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
T_min = 0.210, T_max = 0.311	k = −17→18
32659 measured reflections	l = −19→19

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0361P)² + 0.2346P] where P = (F_o² + 2F_c²)/3
8800 reflections	(Δ/σ)_max = 0.004
261 parameters	Δρ_max = 0.78 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₈H₇Br₂NO₃	γ = 102.401 (1)°
M_r = 324.97	V = 992.45 (3) Å³
Triclinic, P1	Z = 4
a = 7.9591 (1) Å	Mo Kα radiation
b = 11.1949 (2) Å	µ = 8.15 mm⁻¹
c = 12.2509 (2) Å	T = 100 K
α = 106.285 (1)°	0.28 × 0.25 × 0.19 mm
β = 99.691 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	8800 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	7332 reflections with I > 2σ(I)
T_min = 0.210, T_max = 0.311	R_int = 0.027
32659 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.066	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.78 e Å⁻³
8800 reflections	Δρ_min = −0.47 e Å⁻³
261 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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 > 2sigma(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
Br1A	0.79537 (2)	1.230776 (16)	0.197580 (14)	0.02458 (4)
Br2A	0.90786 (2)	1.101536 (16)	0.387687 (13)	0.02180 (4)
O1A	0.76010 (16)	0.62902 (12)	−0.10724 (10)	0.0229 (2)
O2A	0.30267 (16)	0.76549 (13)	0.10327 (11)	0.0265 (2)
O3A	0.37293 (16)	0.96938 (13)	0.11963 (11)	0.0257 (2)
N1A	0.40781 (17)	0.86506 (14)	0.10586 (11)	0.0208 (2)
C1A	0.8937 (2)	0.94163 (16)	0.11837 (13)	0.0209 (3)
H1AA	0.9990	1.0061	0.1578	0.025*
C2A	0.8985 (2)	0.83283 (16)	0.03310 (13)	0.0216 (3)
H2AA	1.0052	0.8260	0.0142	0.026*
C3A	0.7427 (2)	0.73241 (15)	−0.02523 (13)	0.0195 (3)
C4A	0.58321 (19)	0.74374 (15)	0.00283 (13)	0.0188 (2)
H4AA	0.4792	0.6770	−0.0335	0.023*
C5A	0.58299 (19)	0.85699 (15)	0.08631 (13)	0.0185 (2)
C6A	0.73536 (19)	0.95856 (15)	0.14790 (13)	0.0184 (2)
C7A	0.7370 (2)	1.07568 (15)	0.24351 (13)	0.0196 (3)
C8A	0.6054 (2)	0.52136 (17)	−0.16335 (15)	0.0256 (3)
H8AA	0.6344	0.4546	−0.2193	0.038*
H8AB	0.5141	0.5491	−0.2029	0.038*
H8AC	0.5640	0.4883	−0.1055	0.038*
Br1B	−0.20637 (2)	0.726206 (17)	0.325018 (14)	0.02462 (4)
Br2B	−0.10244 (2)	0.523519 (16)	0.125556 (13)	0.02342 (4)
O1B	0.50849 (16)	0.63292 (12)	0.60857 (11)	0.0243 (2)
O2B	0.49443 (16)	0.92884 (12)	0.36858 (11)	0.0252 (2)
O3B	0.22098 (17)	0.93622 (12)	0.34859 (12)	0.0261 (2)
N1B	0.33898 (17)	0.88484 (13)	0.36914 (11)	0.0197 (2)
C1B	0.1045 (2)	0.56681 (15)	0.38962 (13)	0.0206 (3)
H1BA	−0.0019	0.5017	0.3575	0.025*
C2B	0.2309 (2)	0.55536 (16)	0.47501 (14)	0.0215 (3)
H2BA	0.2081	0.4840	0.5005	0.026*
C3B	0.3935 (2)	0.65079 (16)	0.52360 (13)	0.0200 (3)
C4B	0.4281 (2)	0.75603 (15)	0.48395 (13)	0.0199 (3)
H4BA	0.5370	0.8186	0.5131	0.024*
C5B	0.29538 (19)	0.76575 (15)	0.39929 (13)	0.0180 (2)
C6B	0.13101 (19)	0.67357 (15)	0.34948 (13)	0.0185 (2)
C7B	−0.0114 (2)	0.68337 (16)	0.25833 (13)	0.0203 (3)
C8B	0.6731 (2)	0.73163 (19)	0.66117 (16)	0.0289 (3)
H8BA	0.7436	0.7088	0.7196	0.043*
H8BB	0.6504	0.8126	0.6971	0.043*
H8BC	0.7359	0.7397	0.6021	0.043*
H7A	0.627 (3)	1.0704 (19)	0.2645 (17)	0.013 (4)*
H7B	0.022 (3)	0.747 (2)	0.226 (2)	0.028 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1A	0.03013 (8)	0.01907 (7)	0.02323 (7)	0.00585 (6)	0.00401 (6)	0.00714 (6)
Br2A	0.01964 (7)	0.02534 (8)	0.01851 (6)	0.00619 (5)	0.00280 (5)	0.00539 (5)
O1A	0.0221 (5)	0.0217 (5)	0.0231 (5)	0.0078 (4)	0.0056 (4)	0.0033 (4)
O2A	0.0185 (5)	0.0262 (6)	0.0315 (6)	0.0021 (4)	0.0067 (4)	0.0068 (5)
O3A	0.0211 (5)	0.0255 (6)	0.0293 (6)	0.0111 (4)	0.0033 (4)	0.0052 (5)
N1A	0.0171 (5)	0.0232 (6)	0.0198 (5)	0.0060 (5)	0.0029 (4)	0.0043 (5)
C1A	0.0167 (6)	0.0229 (7)	0.0215 (6)	0.0049 (5)	0.0037 (5)	0.0060 (5)
C2A	0.0180 (6)	0.0255 (7)	0.0210 (6)	0.0071 (5)	0.0051 (5)	0.0062 (5)
C3A	0.0206 (6)	0.0198 (7)	0.0185 (6)	0.0076 (5)	0.0039 (5)	0.0061 (5)
C4A	0.0173 (6)	0.0179 (6)	0.0196 (6)	0.0050 (5)	0.0020 (5)	0.0051 (5)
C5A	0.0158 (6)	0.0200 (7)	0.0199 (6)	0.0062 (5)	0.0037 (5)	0.0063 (5)
C6A	0.0173 (6)	0.0189 (6)	0.0186 (6)	0.0051 (5)	0.0036 (5)	0.0060 (5)
C7A	0.0191 (6)	0.0186 (6)	0.0189 (6)	0.0034 (5)	0.0034 (5)	0.0046 (5)
C8A	0.0278 (8)	0.0205 (7)	0.0260 (7)	0.0066 (6)	0.0064 (6)	0.0042 (6)
Br1B	0.01982 (7)	0.02733 (8)	0.02389 (7)	0.00989 (6)	0.00277 (5)	0.00308 (6)
Br2B	0.02590 (7)	0.02424 (8)	0.01841 (6)	0.00830 (6)	0.00365 (5)	0.00441 (5)
O1B	0.0208 (5)	0.0264 (6)	0.0264 (5)	0.0062 (4)	0.0013 (4)	0.0125 (5)
O2B	0.0205 (5)	0.0262 (6)	0.0282 (6)	0.0014 (4)	0.0061 (4)	0.0118 (5)
O3B	0.0262 (6)	0.0224 (6)	0.0327 (6)	0.0100 (5)	0.0059 (5)	0.0122 (5)
N1B	0.0209 (6)	0.0174 (6)	0.0202 (5)	0.0043 (5)	0.0045 (4)	0.0065 (4)
C1B	0.0197 (6)	0.0189 (7)	0.0225 (6)	0.0038 (5)	0.0042 (5)	0.0076 (5)
C2B	0.0211 (6)	0.0197 (7)	0.0251 (7)	0.0055 (5)	0.0058 (5)	0.0094 (5)
C3B	0.0187 (6)	0.0211 (7)	0.0216 (6)	0.0073 (5)	0.0049 (5)	0.0077 (5)
C4B	0.0181 (6)	0.0200 (7)	0.0211 (6)	0.0050 (5)	0.0040 (5)	0.0065 (5)
C5B	0.0191 (6)	0.0165 (6)	0.0196 (6)	0.0055 (5)	0.0057 (5)	0.0066 (5)
C6B	0.0170 (6)	0.0190 (6)	0.0192 (6)	0.0051 (5)	0.0042 (5)	0.0058 (5)
C7B	0.0193 (6)	0.0199 (7)	0.0208 (6)	0.0048 (5)	0.0039 (5)	0.0065 (5)
C8B	0.0228 (7)	0.0303 (9)	0.0301 (8)	0.0047 (6)	−0.0012 (6)	0.0112 (7)

Geometric parameters (Å, º) top

Br1A—C7A	1.9587 (15)	Br1B—C7B	1.9576 (16)
Br2A—C7A	1.9462 (15)	Br2B—C7B	1.9460 (16)
O1A—C3A	1.3535 (19)	O1B—C3B	1.3547 (19)
O1A—C8A	1.433 (2)	O1B—C8B	1.431 (2)
O2A—N1A	1.2306 (18)	O2B—N1B	1.2314 (17)
O3A—N1A	1.2305 (19)	O3B—N1B	1.2288 (18)
N1A—C5A	1.4710 (19)	N1B—C5B	1.4680 (19)
C1A—C2A	1.377 (2)	C1B—C2B	1.378 (2)
C1A—C6A	1.405 (2)	C1B—C6B	1.404 (2)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.402 (2)	C2B—C3B	1.401 (2)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.392 (2)	C3B—C4B	1.388 (2)
C4A—C5A	1.388 (2)	C4B—C5B	1.395 (2)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.397 (2)	C5B—C6B	1.395 (2)
C6A—C7A	1.489 (2)	C6B—C7B	1.497 (2)
C7A—H7A	0.948 (19)	C7B—H7B	0.92 (2)
C8A—H8AA	0.9600	C8B—H8BA	0.9600
C8A—H8AB	0.9600	C8B—H8BB	0.9600
C8A—H8AC	0.9600	C8B—H8BC	0.9600

Br1A···Br2Bⁱ	3.5915 (3)	Br2A···Br1Bⁱⁱ	3.6279 (2)

C3A—O1A—C8A	117.29 (13)	C3B—O1B—C8B	116.75 (13)
O3A—N1A—O2A	123.97 (14)	O3B—N1B—O2B	123.87 (14)
O3A—N1A—C5A	118.23 (13)	O3B—N1B—C5B	118.83 (12)
O2A—N1A—C5A	117.75 (14)	O2B—N1B—C5B	117.28 (13)
C2A—C1A—C6A	122.27 (14)	C2B—C1B—C6B	122.16 (14)
C2A—C1A—H1AA	118.9	C2B—C1B—H1BA	118.9
C6A—C1A—H1AA	118.9	C6B—C1B—H1BA	118.9
C1A—C2A—C3A	120.06 (14)	C1B—C2B—C3B	120.25 (14)
C1A—C2A—H2AA	120.0	C1B—C2B—H2BA	119.9
C3A—C2A—H2AA	120.0	C3B—C2B—H2BA	119.9
O1A—C3A—C4A	124.35 (14)	O1B—C3B—C4B	124.10 (14)
O1A—C3A—C2A	115.97 (13)	O1B—C3B—C2B	116.25 (14)
C4A—C3A—C2A	119.68 (14)	C4B—C3B—C2B	119.65 (14)
C5A—C4A—C3A	118.44 (14)	C3B—C4B—C5B	118.43 (14)
C5A—C4A—H4AA	120.8	C3B—C4B—H4BA	120.8
C3A—C4A—H4AA	120.8	C5B—C4B—H4BA	120.8
C4A—C5A—C6A	123.78 (14)	C4B—C5B—C6B	123.70 (14)
C4A—C5A—N1A	115.23 (13)	C4B—C5B—N1B	114.52 (13)
C6A—C5A—N1A	120.98 (14)	C6B—C5B—N1B	121.73 (13)
C5A—C6A—C1A	115.70 (14)	C5B—C6B—C1B	115.76 (14)
C5A—C6A—C7A	123.71 (13)	C5B—C6B—C7B	123.88 (14)
C1A—C6A—C7A	120.52 (13)	C1B—C6B—C7B	120.36 (13)
C6A—C7A—Br2A	111.59 (11)	C6B—C7B—Br2B	111.47 (11)
C6A—C7A—Br1A	110.77 (10)	C6B—C7B—Br1B	110.83 (10)
Br2A—C7A—Br1A	108.66 (7)	Br2B—C7B—Br1B	109.65 (7)
C6A—C7A—H7A	113.2 (12)	C6B—C7B—H7B	115.7 (15)
Br2A—C7A—H7A	104.8 (12)	Br2B—C7B—H7B	105.1 (15)
Br1A—C7A—H7A	107.5 (12)	Br1B—C7B—H7B	103.7 (15)
O1A—C8A—H8AA	109.5	O1B—C8B—H8BA	109.5
O1A—C8A—H8AB	109.5	O1B—C8B—H8BB	109.5
H8AA—C8A—H8AB	109.5	H8BA—C8B—H8BB	109.5
O1A—C8A—H8AC	109.5	O1B—C8B—H8BC	109.5
H8AA—C8A—H8AC	109.5	H8BA—C8B—H8BC	109.5
H8AB—C8A—H8AC	109.5	H8BB—C8B—H8BC	109.5

C6A—C1A—C2A—C3A	−1.9 (2)	C6B—C1B—C2B—C3B	−1.1 (2)
C8A—O1A—C3A—C4A	−3.9 (2)	C8B—O1B—C3B—C4B	1.5 (2)
C8A—O1A—C3A—C2A	176.29 (14)	C8B—O1B—C3B—C2B	−178.30 (15)
C1A—C2A—C3A—O1A	−179.68 (14)	C1B—C2B—C3B—O1B	178.77 (15)
C1A—C2A—C3A—C4A	0.5 (2)	C1B—C2B—C3B—C4B	−1.1 (2)
O1A—C3A—C4A—C5A	−178.01 (14)	O1B—C3B—C4B—C5B	−177.36 (15)
C2A—C3A—C4A—C5A	1.8 (2)	C2B—C3B—C4B—C5B	2.4 (2)
C3A—C4A—C5A—C6A	−2.9 (2)	C3B—C4B—C5B—C6B	−1.9 (2)
C3A—C4A—C5A—N1A	176.35 (13)	C3B—C4B—C5B—N1B	175.71 (14)
O3A—N1A—C5A—C4A	−139.68 (14)	O3B—N1B—C5B—C4B	−142.98 (15)
O2A—N1A—C5A—C4A	37.79 (19)	O2B—N1B—C5B—C4B	35.46 (19)
O3A—N1A—C5A—C6A	39.6 (2)	O3B—N1B—C5B—C6B	34.7 (2)
O2A—N1A—C5A—C6A	−142.94 (15)	O2B—N1B—C5B—C6B	−146.90 (14)
C4A—C5A—C6A—C1A	1.6 (2)	C4B—C5B—C6B—C1B	−0.1 (2)
N1A—C5A—C6A—C1A	−177.63 (13)	N1B—C5B—C6B—C1B	−177.56 (14)
C4A—C5A—C6A—C7A	−175.35 (14)	C4B—C5B—C6B—C7B	−179.76 (15)
N1A—C5A—C6A—C7A	5.5 (2)	N1B—C5B—C6B—C7B	2.8 (2)
C2A—C1A—C6A—C5A	0.9 (2)	C2B—C1B—C6B—C5B	1.6 (2)
C2A—C1A—C6A—C7A	177.90 (14)	C2B—C1B—C6B—C7B	−178.73 (15)
C5A—C6A—C7A—Br2A	124.47 (14)	C5B—C6B—C7B—Br2B	130.42 (13)
C1A—C6A—C7A—Br2A	−52.30 (17)	C1B—C6B—C7B—Br2B	−49.18 (17)
C5A—C6A—C7A—Br1A	−114.33 (14)	C5B—C6B—C7B—Br1B	−107.15 (14)
C1A—C6A—C7A—Br1A	68.89 (16)	C1B—C6B—C7B—Br1B	73.24 (17)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7A—H7A···O2B	0.95 (2)	2.47 (2)	3.134 (2)	126.8 (17)
C8B—H8BA···O1Aⁱⁱⁱ	0.96	2.52	3.370 (2)	148
C8A—H8AA···Cg2^iv	0.96	2.95	3.839 (2)	155

Symmetry codes: (iii) x, y, z+1; (iv) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₈H₇Br₂NO₃
M_r	324.97
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.9591 (1), 11.1949 (2), 12.2509 (2)
α, β, γ (°)	106.285 (1), 99.691 (1), 102.401 (1)
V (Å³)	992.45 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	8.15
Crystal size (mm)	0.28 × 0.25 × 0.19

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.210, 0.311
No. of measured, independent and observed [I > 2σ(I)] reflections	32659, 8800, 7332
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.812

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.066, 1.01
No. of reflections	8800
No. of parameters	261
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.78, −0.47

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected interatomic distances (Å) top

Br1A···Br2Bⁱ

3.5915 (3)

Br2A···Br1Bⁱⁱ

3.6279 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7A—H7A···O2B	0.95 (2)	2.47 (2)	3.134 (2)	126.8 (17)
C8B—H8BA···O1Aⁱⁱⁱ	0.9600	2.5200	3.370 (2)	148.00
C8A—H8AA···Cg2^iv	0.9600	2.9500	3.839 (2)	155.00

Symmetry codes: (iii) x, y, z+1; (iv) −x+1, −y+1, −z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and JHG thank Universiti Sains Malaysia (USM) for the Research Universiti Golden Goose Grant (No. 1001/PFIZIK/811012). JHG thanks USM for the award of a USM Fellowship. AMI is grateful to the Director, NITK, Surathkal, India, for providing research facilities.

References

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