4-Amino-3-bromo­benzoic acid

Arshad, M.N.; Tahir, M.N.; Khan, I.U.; Shafiq, M.; Waheed, A.

doi:10.1107/S1600536809006825

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o640

doi:10.1107/S1600536809006825

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4-Amino-3-bromobenzoic acid

Muhammad Nadeem Arshad,^a M. Nawaz Tahir,^b ^* Islam Ullah Khan,^a Muhammad Shafiq ^a and Abdul Waheed ^a

^aDepartment of Chemistry, Government College University, Lahore, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 1 February 2009; accepted 24 February 2009; online 28 February 2009)

The asymmetric unit of the title compound, C₇H₆BrNO₂, consists of two molecules having a small variation of bond lengths and angles. The title compound forms dimers through pairs of O—H⋯O hydrogen bonds involving the carboxylate groups. The dimers are linked into polymeric forms through intermolecular hydrogen bonds, forming R₂¹(6), R₃²(8) and R₃³(15) ring motifs.

Related literature

The title compound has been prepared as an intermediate for the synthesis of sulfonamides (Arshad et al., 2009 ) and benzothiazines (Arshad et al., 2008 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For related structures, see: Pant (1965 ); Tanaka et al. (1967 ). For the synthesis, see: Krishna Mohan et al. (2004 ).

Experimental

Crystal data

C₇H₆BrNO₂
M_r = 216.04
Orthorhombic, P n a 2₁
a = 24.3968 (11) Å
b = 4.8388 (2) Å
c = 12.8040 (5) Å
V = 1511.53 (11) Å³
Z = 8
Mo Kα radiation
μ = 5.38 mm⁻¹
T = 296 K
0.22 × 0.16 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.375, T_max = 0.469
9922 measured reflections
3908 independent reflections
3169 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.059
S = 1.00
3908 reflections
214 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.49 e Å⁻³
Absolute structure: Flack (1983 ), 1857 Friedel pairs
Flack parameter: 0.012 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4ⁱ	0.82	1.76	2.564 (3)	165
N1—H1A⋯Br1	0.92 (4)	2.63 (4)	3.081 (4)	111 (3)
N1—H1B⋯O2ⁱⁱ	0.83 (5)	2.57 (5)	3.313 (4)	149 (4)
N2—H2A⋯Br2	0.99 (4)	2.68 (4)	3.099 (4)	106 (2)
N2—H2A⋯Br1ⁱⁱ	0.99 (4)	2.69 (4)	3.630 (4)	158 (3)
N2—H2B⋯O1ⁱⁱⁱ	0.79 (5)	2.43 (5)	3.216 (4)	179 (6)
O3—H3⋯O2^iv	0.82	1.90	2.723 (3)	178
C5—H5⋯O2ⁱⁱ	0.93	2.59	3.407 (4)	147
C12—H12⋯O4^v	0.93	2.54	3.470 (4)	174
Symmetry codes: (i) $[-x, -y+2, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x, y-1, z; (iv) $[-x, -y+2, z+{\script{1\over 2}}]$ ; (v) $[-x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006825/bq2123sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809006825/bq2123Isup2.hkl

checkCIF report

Comment top

Different types of aromatic anilines have been used for the synthesis of carboxamides and sulfonamides. The title compound (I), (Fig 1), has been prepared as an intermediate for the synthesis of sulfonamides (Arshad et al., 2009), benzothiazines (Arshad et al., 2008) and different metal complexes.

The crystal structure of m-Bromobenzoic acid (Tanaka et al., 1967) and 3,5-Dibromo-p-aminobenzoic acid (Pant, 1965) has been published. The title compound consists of an asymmetric unit having two chemical isomers. There is a small variation of bond lengths and bond angles among the two isomers and both isomers form five membered ring (Br/C/C/N/H) through intramolecular H-bond of type N—H···Br. The molecules are dimerized forming R₂²(8) ring motifs (Bernstein et al., 1995). These dimers are linked to each other through R₂¹(6), R₃²(8) and R₃³(15) ring motifs (Table 1), (Fig 2).

Related literature top

The title compound was prepared as an intermediate for the synthesis of sulfonamides (Arshad et al., 2009), benzothiazines (Arshad et al., 2008). For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Pant (1965); Tanaka et al. (1967). For the synthesis, see: Krishna Mohan et al. (2004);

Experimental top

The title copound was prepared following the same method (Krishna Mohan et al., 2004) available in literature. 4-Amino Benzoic acid (2 g, 0.0146 mol) and ammonium bromide (1.5 g, 0.16 mol) was charged to a flask (25 ml) containing acetic acid (15 ml). Hydrogen peroxide (0.545 g, 0.016 mol) was added drop wise to the above mixture and allowed to stirr at room temperature for 3 h. Stirring was stoped and allowed it to setteled down. Precipitate obtained was filtered and washed with water and recrystalizesd in dichloromethane and methanol for X-ray studies.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. ORTEP drawing of the title compound, with the atom numbering scheme. The thermal ellipsoids are drawn at the 30% probability level. The dotted lines show the intramolecular H-bonds.
	Fig. 2. The projectional view (PLATON: Spek, 2009) which shows that molecules are dimerized and form ring motifs.

4-Amino-3-bromobenzoic acid top

Crystal data top

C₇H₆BrNO₂	F(000) = 848
M_r = 216.04	D_x = 1.899 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3169 reflections
a = 24.3968 (11) Å	θ = 1.7–28.7°
b = 4.8388 (2) Å	µ = 5.38 mm⁻¹
c = 12.8040 (5) Å	T = 296 K
V = 1511.53 (11) Å³	Prismatic, colorless
Z = 8	0.22 × 0.16 × 0.14 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3908 independent reflections
Radiation source: fine-focus sealed tube	3169 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 7.40 pixels mm^-1	θ_max = 28.7°, θ_min = 1.7°
ω scans	h = −32→33
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→5
T_min = 0.375, T_max = 0.469	l = −17→17
9922 measured reflections

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)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.059	w = 1/[σ²(F_o²) + (0.0107P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
3908 reflections	Δρ_max = 0.44 e Å⁻³
214 parameters	Δρ_min = −0.49 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1857 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.012 (9)

Crystal data top

C₇H₆BrNO₂	V = 1511.53 (11) Å³
M_r = 216.04	Z = 8
Orthorhombic, Pna2₁	Mo Kα radiation
a = 24.3968 (11) Å	µ = 5.38 mm⁻¹
b = 4.8388 (2) Å	T = 296 K
c = 12.8040 (5) Å	0.22 × 0.16 × 0.14 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3908 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3169 reflections with I > 2σ(I)
T_min = 0.375, T_max = 0.469	R_int = 0.027
9922 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.059	Δρ_max = 0.44 e Å⁻³
S = 1.00	Δρ_min = −0.49 e Å⁻³
3908 reflections	Absolute structure: Flack (1983), 1857 Friedel pairs
214 parameters	Absolute structure parameter: 0.012 (9)
1 restraint

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	0.320114 (15)	−0.05594 (7)	0.25848 (2)	0.03957 (10)
O1	0.14368 (11)	0.8516 (5)	0.40595 (16)	0.0440 (6)
H1	0.1288	0.9846	0.3781	0.053*
O2	0.16062 (9)	0.7357 (4)	0.24087 (17)	0.0350 (5)
N1	0.33671 (15)	0.0202 (8)	0.4953 (3)	0.0510 (10)
H1A	0.3479 (16)	−0.127 (8)	0.455 (3)	0.061*
H1B	0.3387 (19)	0.004 (8)	0.560 (4)	0.061*
C1	0.21062 (12)	0.5149 (6)	0.3765 (3)	0.0302 (6)
C2	0.23965 (12)	0.3438 (6)	0.3108 (2)	0.0288 (7)
H2	0.2318	0.3416	0.2397	0.035*
C3	0.28043 (13)	0.1752 (6)	0.3501 (2)	0.0275 (7)
C4	0.29402 (14)	0.1757 (7)	0.4569 (3)	0.0339 (8)
C5	0.26337 (14)	0.3430 (8)	0.5214 (3)	0.0428 (9)
H5	0.2702	0.3409	0.5928	0.051*
C6	0.22328 (15)	0.5119 (7)	0.4833 (3)	0.0416 (9)
H6	0.2041	0.6265	0.5287	0.050*
C7	0.16965 (14)	0.7060 (7)	0.3350 (3)	0.0312 (8)
Br2	0.068709 (14)	−0.02802 (6)	0.87184 (3)	0.03738 (9)
O3	−0.09440 (11)	0.8621 (5)	0.66215 (19)	0.0441 (6)
H3	−0.1136	0.9859	0.6862	0.053*
O4	−0.08170 (10)	0.7685 (5)	0.83152 (18)	0.0400 (6)
N2	0.09823 (15)	−0.0184 (7)	0.6365 (3)	0.0468 (9)
H2A	0.1139 (15)	−0.152 (7)	0.687 (3)	0.056*
H2B	0.1093 (17)	−0.052 (8)	0.580 (4)	0.056*
C8	−0.02918 (14)	0.5234 (6)	0.7088 (3)	0.0284 (7)
C9	−0.00474 (13)	0.3632 (6)	0.7867 (2)	0.0281 (7)
H9	−0.0167	0.3786	0.8554	0.034*
C10	0.03682 (12)	0.1830 (6)	0.7625 (3)	0.0286 (6)
C11	0.05602 (13)	0.1496 (7)	0.6603 (3)	0.0305 (7)
C12	0.03023 (14)	0.3106 (8)	0.5824 (2)	0.0400 (8)
H12	0.0416	0.2949	0.5134	0.048*
C13	−0.01099 (15)	0.4883 (6)	0.6068 (3)	0.0371 (8)
H13	−0.0275	0.5894	0.5537	0.045*
C14	−0.07084 (13)	0.7263 (6)	0.7391 (3)	0.0315 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03529 (19)	0.04090 (18)	0.0425 (2)	0.00405 (15)	0.00077 (17)	−0.0027 (2)
O1	0.0561 (17)	0.0506 (15)	0.0252 (12)	0.0258 (13)	0.0033 (11)	0.0052 (11)
O2	0.0373 (13)	0.0412 (13)	0.0265 (13)	0.0111 (9)	0.0002 (10)	0.0058 (10)
N1	0.049 (2)	0.069 (2)	0.0351 (19)	0.0173 (16)	−0.0101 (17)	0.0089 (16)
C1	0.0271 (15)	0.0389 (15)	0.0246 (15)	0.0026 (13)	−0.0001 (16)	0.0062 (15)
C2	0.0250 (18)	0.0351 (18)	0.0264 (17)	−0.0012 (14)	−0.0023 (13)	0.0040 (14)
C3	0.0254 (17)	0.0300 (16)	0.027 (2)	0.0002 (13)	0.0000 (13)	0.0040 (13)
C4	0.0293 (19)	0.0360 (19)	0.036 (2)	0.0029 (15)	−0.0073 (14)	0.0071 (16)
C5	0.044 (2)	0.060 (2)	0.0246 (17)	0.0105 (19)	−0.0050 (16)	−0.0015 (17)
C6	0.039 (2)	0.051 (2)	0.034 (2)	0.0133 (16)	0.0008 (16)	0.0011 (16)
C7	0.032 (2)	0.0305 (17)	0.0310 (19)	−0.0003 (14)	0.0025 (15)	0.0055 (15)
Br2	0.03815 (19)	0.03913 (17)	0.03487 (17)	0.00381 (15)	−0.00324 (17)	0.0049 (2)
O3	0.0484 (16)	0.0458 (15)	0.0381 (14)	0.0211 (12)	−0.0097 (12)	−0.0080 (12)
O4	0.0403 (16)	0.0471 (15)	0.0326 (13)	0.0124 (12)	−0.0019 (11)	−0.0078 (11)
N2	0.053 (2)	0.054 (2)	0.0327 (18)	0.0179 (16)	0.0056 (16)	−0.0052 (16)
C8	0.0292 (17)	0.0257 (15)	0.0303 (17)	0.0030 (13)	−0.0028 (14)	−0.0054 (13)
C9	0.0309 (18)	0.0323 (16)	0.0212 (16)	−0.0029 (14)	0.0027 (12)	−0.0047 (12)
C10	0.0310 (16)	0.0269 (14)	0.0278 (16)	−0.0003 (12)	−0.0057 (15)	0.0013 (16)
C11	0.0285 (17)	0.0335 (17)	0.0296 (17)	0.0008 (14)	−0.0003 (14)	−0.0041 (15)
C12	0.044 (2)	0.055 (2)	0.0206 (17)	0.0048 (17)	0.0046 (15)	−0.0024 (15)
C13	0.046 (2)	0.0403 (17)	0.0254 (19)	0.0058 (16)	−0.0058 (15)	0.0011 (14)
C14	0.0302 (17)	0.0287 (16)	0.035 (2)	0.0012 (12)	−0.0015 (16)	−0.0019 (14)

Geometric parameters (Å, º) top

Br1—C3	1.888 (3)	Br2—C10	1.899 (3)
O1—C7	1.312 (4)	O3—C14	1.316 (4)
O1—H1	0.8200	O3—H3	0.8200
O2—C7	1.234 (3)	O4—C14	1.230 (3)
N1—C4	1.376 (4)	N2—C11	1.347 (5)
N1—H1A	0.92 (4)	N2—H2A	0.99 (4)
N1—H1B	0.83 (4)	N2—H2B	0.79 (4)
C1—C2	1.376 (5)	C8—C13	1.390 (5)
C1—C6	1.402 (5)	C8—C9	1.397 (4)
C1—C7	1.462 (5)	C8—C14	1.465 (4)
C2—C3	1.382 (4)	C9—C10	1.373 (4)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.407 (4)	C10—C11	1.400 (5)
C4—C5	1.377 (5)	C11—C12	1.413 (5)
C5—C6	1.365 (5)	C12—C13	1.360 (5)
C5—H5	0.9300	C12—H12	0.9300
C6—H6	0.9300	C13—H13	0.9300

C7—O1—H1	109.5	C14—O3—H3	109.5
C4—N1—H1A	116 (2)	C11—N2—H2A	123 (2)
C4—N1—H1B	117 (3)	C11—N2—H2B	126 (3)
H1A—N1—H1B	118 (4)	H2A—N2—H2B	109 (4)
C2—C1—C6	118.5 (3)	C13—C8—C9	117.8 (3)
C2—C1—C7	120.7 (3)	C13—C8—C14	123.5 (3)
C6—C1—C7	120.7 (3)	C9—C8—C14	118.7 (3)
C1—C2—C3	120.2 (3)	C10—C9—C8	120.5 (3)
C1—C2—H2	119.9	C10—C9—H9	119.7
C3—C2—H2	119.9	C8—C9—H9	119.7
C2—C3—C4	121.5 (3)	C9—C10—C11	122.1 (3)
C2—C3—Br1	119.5 (2)	C9—C10—Br2	118.6 (2)
C4—C3—Br1	119.0 (2)	C11—C10—Br2	119.4 (2)
N1—C4—C5	121.3 (3)	N2—C11—C10	122.5 (3)
N1—C4—C3	121.6 (3)	N2—C11—C12	120.9 (3)
C5—C4—C3	117.1 (3)	C10—C11—C12	116.6 (3)
C6—C5—C4	121.8 (3)	C13—C12—C11	121.0 (3)
C6—C5—H5	119.1	C13—C12—H12	119.5
C4—C5—H5	119.1	C11—C12—H12	119.5
C5—C6—C1	120.8 (3)	C12—C13—C8	122.0 (3)
C5—C6—H6	119.6	C12—C13—H13	119.0
C1—C6—H6	119.6	C8—C13—H13	119.0
O2—C7—O1	121.8 (3)	O4—C14—O3	122.9 (3)
O2—C7—C1	123.4 (3)	O4—C14—C8	121.0 (3)
O1—C7—C1	114.7 (3)	O3—C14—C8	116.1 (3)

C6—C1—C2—C3	−0.4 (4)	C13—C8—C9—C10	1.7 (5)
C7—C1—C2—C3	176.3 (3)	C14—C8—C9—C10	−176.0 (3)
C1—C2—C3—C4	−0.9 (5)	C8—C9—C10—C11	−0.7 (5)
C1—C2—C3—Br1	−179.5 (2)	C8—C9—C10—Br2	179.7 (2)
C2—C3—C4—N1	−176.1 (3)	C9—C10—C11—N2	177.3 (3)
Br1—C3—C4—N1	2.5 (5)	Br2—C10—C11—N2	−3.1 (4)
C2—C3—C4—C5	2.7 (5)	C9—C10—C11—C12	−0.2 (5)
Br1—C3—C4—C5	−178.7 (3)	Br2—C10—C11—C12	179.4 (2)
N1—C4—C5—C6	175.6 (4)	N2—C11—C12—C13	−177.4 (3)
C3—C4—C5—C6	−3.2 (6)	C10—C11—C12—C13	0.1 (5)
C4—C5—C6—C1	2.0 (6)	C11—C12—C13—C8	1.0 (6)
C2—C1—C6—C5	−0.1 (5)	C9—C8—C13—C12	−1.8 (5)
C7—C1—C6—C5	−176.8 (3)	C14—C8—C13—C12	175.7 (3)
C2—C1—C7—O2	−3.7 (5)	C13—C8—C14—O4	−172.8 (3)
C6—C1—C7—O2	172.9 (3)	C9—C8—C14—O4	4.7 (5)
C2—C1—C7—O1	178.0 (3)	C13—C8—C14—O3	5.7 (5)
C6—C1—C7—O1	−5.3 (5)	C9—C8—C14—O3	−176.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.82	1.76	2.564 (3)	165
N1—H1A···Br1	0.92 (4)	2.63 (4)	3.081 (4)	111 (3)
N1—H1B···O2ⁱⁱ	0.83 (5)	2.57 (5)	3.313 (4)	149 (4)
N2—H2A···Br2	0.99 (4)	2.68 (4)	3.099 (4)	106 (2)
N2—H2A···Br1ⁱⁱ	0.99 (4)	2.69 (4)	3.630 (4)	158 (3)
N2—H2B···O1ⁱⁱⁱ	0.79 (5)	2.43 (5)	3.216 (4)	179 (6)
O3—H3···O2^iv	0.82	1.90	2.723 (3)	178
C5—H5···O2ⁱⁱ	0.93	2.59	3.407 (4)	147
C12—H12···O4^v	0.93	2.54	3.470 (4)	174

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

Experimental details

Crystal data
Chemical formula	C₇H₆BrNO₂
M_r	216.04
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	296
a, b, c (Å)	24.3968 (11), 4.8388 (2), 12.8040 (5)
V (Å³)	1511.53 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	5.38
Crystal size (mm)	0.22 × 0.16 × 0.14

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.375, 0.469
No. of measured, independent and observed [I > 2σ(I)] reflections	9922, 3908, 3169
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.059, 1.00
No. of reflections	3908
No. of parameters	214
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.49
Absolute structure	Flack (1983), 1857 Friedel pairs
Absolute structure parameter	0.012 (9)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.8200	1.7600	2.564 (3)	165.00
N1—H1A···Br1	0.92 (4)	2.63 (4)	3.081 (4)	111 (3)
N1—H1B···O2ⁱⁱ	0.83 (5)	2.57 (5)	3.313 (4)	149 (4)
N2—H2A···Br2	0.99 (4)	2.68 (4)	3.099 (4)	106 (2)
N2—H2A···Br1ⁱⁱ	0.99 (4)	2.69 (4)	3.630 (4)	158 (3)
N2—H2B···O1ⁱⁱⁱ	0.79 (5)	2.43 (5)	3.216 (4)	179 (6)
O3—H3···O2^iv	0.8200	1.9000	2.723 (3)	178.00
C5—H5···O2ⁱⁱ	0.9300	2.5900	3.407 (4)	147.00
C12—H12···O4^v	0.9300	2.5400	3.470 (4)	174.00

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

Acknowledgements

MNA greatfully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing him with a Scholaship under the Indigenous PhD Program (PIN 042–120607-PS2–183).

References

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