Literature DB >> 21582289

4-Amino-3-bromo-benzoic acid.

Muhammad Nadeem Arshad, M Nawaz Tahir, Islam Ullah Khan, Muhammad Shafiq, Abdul Waheed.   

Abstract

The asymmetric unit of the title compound, C(7)H(6)BrNO(2), consists of two mol-ecules having a small variation of bond lengths and angles. The title compound forms dimers through pairs of O-H⋯O hydrogen bonds involving the carboxyl-ate groups. The dimers are linked into polymeric forms through inter-molecular hydrogen bonds, forming R(2) (1)(6), R(3) (2)(8) and R(3) (3)(15) ring motifs.

Entities:  

Year:  2009        PMID： 21582289      PMCID： PMC2968661          DOI： 10.1107/S1600536809006825

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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 = 216.04 Orthorhombic, 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[F 2 > 2σ(F 2)] = 0.030 wR(F 2) = 0.059 S = 1.00 3908 reflections 214 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.44 e Å−3 Δρmin = −0.49 e Å−3 Absolute structure: Flack (1983 ▶), 1857 Friedel pairs Flack parameter: 0.012 (9) 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. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006825/bq2123sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006825/bq2123Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C7H6BrNO2F(000) = 848
Mr = 216.04Dx = 1.899 Mg m−3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 3169 reflections
a = 24.3968 (11) Åθ = 1.7–28.7°
b = 4.8388 (2) ŵ = 5.38 mm−1
c = 12.8040 (5) ÅT = 296 K
V = 1511.53 (11) Å3Prismatic, colorless
Z = 80.22 × 0.16 × 0.14 mm
Bruker Kappa APEXII CCD diffractometer3908 independent reflections
Radiation source: fine-focus sealed tube3169 reflections with I > 2σ(I)
graphiteRint = 0.027
Detector resolution: 7.40 pixels mm-1θmax = 28.7°, θmin = 1.7°
ω scansh = −32→33
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −6→5
Tmin = 0.375, Tmax = 0.469l = −17→17
9922 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.059w = 1/[σ2(Fo2) + (0.0107P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
3908 reflectionsΔρmax = 0.44 e Å−3
214 parametersΔρmin = −0.49 e Å−3
1 restraintAbsolute structure: Flack (1983), 1857 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.012 (9)
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.
xyzUiso*/Ueq
Br10.320114 (15)−0.05594 (7)0.25848 (2)0.03957 (10)
O10.14368 (11)0.8516 (5)0.40595 (16)0.0440 (6)
H10.12880.98460.37810.053*
O20.16062 (9)0.7357 (4)0.24087 (17)0.0350 (5)
N10.33671 (15)0.0202 (8)0.4953 (3)0.0510 (10)
H1A0.3479 (16)−0.127 (8)0.455 (3)0.061*
H1B0.3387 (19)0.004 (8)0.560 (4)0.061*
C10.21062 (12)0.5149 (6)0.3765 (3)0.0302 (6)
C20.23965 (12)0.3438 (6)0.3108 (2)0.0288 (7)
H20.23180.34160.23970.035*
C30.28043 (13)0.1752 (6)0.3501 (2)0.0275 (7)
C40.29402 (14)0.1757 (7)0.4569 (3)0.0339 (8)
C50.26337 (14)0.3430 (8)0.5214 (3)0.0428 (9)
H50.27020.34090.59280.051*
C60.22328 (15)0.5119 (7)0.4833 (3)0.0416 (9)
H60.20410.62650.52870.050*
C70.16965 (14)0.7060 (7)0.3350 (3)0.0312 (8)
Br20.068709 (14)−0.02802 (6)0.87184 (3)0.03738 (9)
O3−0.09440 (11)0.8621 (5)0.66215 (19)0.0441 (6)
H3−0.11360.98590.68620.053*
O4−0.08170 (10)0.7685 (5)0.83152 (18)0.0400 (6)
N20.09823 (15)−0.0184 (7)0.6365 (3)0.0468 (9)
H2A0.1139 (15)−0.152 (7)0.687 (3)0.056*
H2B0.1093 (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)
H9−0.01670.37860.85540.034*
C100.03682 (12)0.1830 (6)0.7625 (3)0.0286 (6)
C110.05602 (13)0.1496 (7)0.6603 (3)0.0305 (7)
C120.03023 (14)0.3106 (8)0.5824 (2)0.0400 (8)
H120.04160.29490.51340.048*
C13−0.01099 (15)0.4883 (6)0.6068 (3)0.0371 (8)
H13−0.02750.58940.55370.045*
C14−0.07084 (13)0.7263 (6)0.7391 (3)0.0315 (7)
U11U22U33U12U13U23
Br10.03529 (19)0.04090 (18)0.0425 (2)0.00405 (15)0.00077 (17)−0.0027 (2)
O10.0561 (17)0.0506 (15)0.0252 (12)0.0258 (13)0.0033 (11)0.0052 (11)
O20.0373 (13)0.0412 (13)0.0265 (13)0.0111 (9)0.0002 (10)0.0058 (10)
N10.049 (2)0.069 (2)0.0351 (19)0.0173 (16)−0.0101 (17)0.0089 (16)
C10.0271 (15)0.0389 (15)0.0246 (15)0.0026 (13)−0.0001 (16)0.0062 (15)
C20.0250 (18)0.0351 (18)0.0264 (17)−0.0012 (14)−0.0023 (13)0.0040 (14)
C30.0254 (17)0.0300 (16)0.027 (2)0.0002 (13)0.0000 (13)0.0040 (13)
C40.0293 (19)0.0360 (19)0.036 (2)0.0029 (15)−0.0073 (14)0.0071 (16)
C50.044 (2)0.060 (2)0.0246 (17)0.0105 (19)−0.0050 (16)−0.0015 (17)
C60.039 (2)0.051 (2)0.034 (2)0.0133 (16)0.0008 (16)0.0011 (16)
C70.032 (2)0.0305 (17)0.0310 (19)−0.0003 (14)0.0025 (15)0.0055 (15)
Br20.03815 (19)0.03913 (17)0.03487 (17)0.00381 (15)−0.00324 (17)0.0049 (2)
O30.0484 (16)0.0458 (15)0.0381 (14)0.0211 (12)−0.0097 (12)−0.0080 (12)
O40.0403 (16)0.0471 (15)0.0326 (13)0.0124 (12)−0.0019 (11)−0.0078 (11)
N20.053 (2)0.054 (2)0.0327 (18)0.0179 (16)0.0056 (16)−0.0052 (16)
C80.0292 (17)0.0257 (15)0.0303 (17)0.0030 (13)−0.0028 (14)−0.0054 (13)
C90.0309 (18)0.0323 (16)0.0212 (16)−0.0029 (14)0.0027 (12)−0.0047 (12)
C100.0310 (16)0.0269 (14)0.0278 (16)−0.0003 (12)−0.0057 (15)0.0013 (16)
C110.0285 (17)0.0335 (17)0.0296 (17)0.0008 (14)−0.0003 (14)−0.0041 (15)
C120.044 (2)0.055 (2)0.0206 (17)0.0048 (17)0.0046 (15)−0.0024 (15)
C130.046 (2)0.0403 (17)0.0254 (19)0.0058 (16)−0.0058 (15)0.0011 (14)
C140.0302 (17)0.0287 (16)0.035 (2)0.0012 (12)−0.0015 (16)−0.0019 (14)
Br1—C31.888 (3)Br2—C101.899 (3)
O1—C71.312 (4)O3—C141.316 (4)
O1—H10.8200O3—H30.8200
O2—C71.234 (3)O4—C141.230 (3)
N1—C41.376 (4)N2—C111.347 (5)
N1—H1A0.92 (4)N2—H2A0.99 (4)
N1—H1B0.83 (4)N2—H2B0.79 (4)
C1—C21.376 (5)C8—C131.390 (5)
C1—C61.402 (5)C8—C91.397 (4)
C1—C71.462 (5)C8—C141.465 (4)
C2—C31.382 (4)C9—C101.373 (4)
C2—H20.9300C9—H90.9300
C3—C41.407 (4)C10—C111.400 (5)
C4—C51.377 (5)C11—C121.413 (5)
C5—C61.365 (5)C12—C131.360 (5)
C5—H50.9300C12—H120.9300
C6—H60.9300C13—H130.9300
C7—O1—H1109.5C14—O3—H3109.5
C4—N1—H1A116 (2)C11—N2—H2A123 (2)
C4—N1—H1B117 (3)C11—N2—H2B126 (3)
H1A—N1—H1B118 (4)H2A—N2—H2B109 (4)
C2—C1—C6118.5 (3)C13—C8—C9117.8 (3)
C2—C1—C7120.7 (3)C13—C8—C14123.5 (3)
C6—C1—C7120.7 (3)C9—C8—C14118.7 (3)
C1—C2—C3120.2 (3)C10—C9—C8120.5 (3)
C1—C2—H2119.9C10—C9—H9119.7
C3—C2—H2119.9C8—C9—H9119.7
C2—C3—C4121.5 (3)C9—C10—C11122.1 (3)
C2—C3—Br1119.5 (2)C9—C10—Br2118.6 (2)
C4—C3—Br1119.0 (2)C11—C10—Br2119.4 (2)
N1—C4—C5121.3 (3)N2—C11—C10122.5 (3)
N1—C4—C3121.6 (3)N2—C11—C12120.9 (3)
C5—C4—C3117.1 (3)C10—C11—C12116.6 (3)
C6—C5—C4121.8 (3)C13—C12—C11121.0 (3)
C6—C5—H5119.1C13—C12—H12119.5
C4—C5—H5119.1C11—C12—H12119.5
C5—C6—C1120.8 (3)C12—C13—C8122.0 (3)
C5—C6—H6119.6C12—C13—H13119.0
C1—C6—H6119.6C8—C13—H13119.0
O2—C7—O1121.8 (3)O4—C14—O3122.9 (3)
O2—C7—C1123.4 (3)O4—C14—C8121.0 (3)
O1—C7—C1114.7 (3)O3—C14—C8116.1 (3)
C6—C1—C2—C3−0.4 (4)C13—C8—C9—C101.7 (5)
C7—C1—C2—C3176.3 (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—Br2179.7 (2)
C2—C3—C4—N1−176.1 (3)C9—C10—C11—N2177.3 (3)
Br1—C3—C4—N12.5 (5)Br2—C10—C11—N2−3.1 (4)
C2—C3—C4—C52.7 (5)C9—C10—C11—C12−0.2 (5)
Br1—C3—C4—C5−178.7 (3)Br2—C10—C11—C12179.4 (2)
N1—C4—C5—C6175.6 (4)N2—C11—C12—C13−177.4 (3)
C3—C4—C5—C6−3.2 (6)C10—C11—C12—C130.1 (5)
C4—C5—C6—C12.0 (6)C11—C12—C13—C81.0 (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—C12175.7 (3)
C2—C1—C7—O2−3.7 (5)C13—C8—C14—O4−172.8 (3)
C6—C1—C7—O2172.9 (3)C9—C8—C14—O44.7 (5)
C2—C1—C7—O1178.0 (3)C13—C8—C14—O35.7 (5)
C6—C1—C7—O1−5.3 (5)C9—C8—C14—O3−176.8 (3)
D—H···AD—HH···AD···AD—H···A
O1—H1···O4i0.821.762.564 (3)165
N1—H1A···Br10.92 (4)2.63 (4)3.081 (4)111 (3)
N1—H1B···O2ii0.83 (5)2.57 (5)3.313 (4)149 (4)
N2—H2A···Br20.99 (4)2.68 (4)3.099 (4)106 (2)
N2—H2A···Br1ii0.99 (4)2.69 (4)3.630 (4)158 (3)
N2—H2B···O1iii0.79 (5)2.43 (5)3.216 (4)179 (6)
O3—H3···O2iv0.821.902.723 (3)178
C5—H5···O2ii0.932.593.407 (4)147
C12—H12···O4v0.932.543.470 (4)174
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H1⋯O4i0.821.762.564 (3)165
N1—H1A⋯Br10.92 (4)2.63 (4)3.081 (4)111 (3)
N1—H1B⋯O2ii0.83 (5)2.57 (5)3.313 (4)149 (4)
N2—H2A⋯Br20.99 (4)2.68 (4)3.099 (4)106 (2)
N2—H2A⋯Br1ii0.99 (4)2.69 (4)3.630 (4)158 (3)
N2—H2B⋯O1iii0.79 (5)2.43 (5)3.216 (4)179 (6)
O3—H3⋯O2iv0.821.902.723 (3)178
C5—H5⋯O2ii0.932.593.407 (4)147
C12—H12⋯O4v0.932.543.470 (4)174

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

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