4-Bromo-2-hy­droxy­benzoic acid

Suchetan, P.A.; Suneetha, V.; Naveen, S.; Lokanath, N.K.; Krishna Murthy, P.

doi:10.1107/S2414314616003254

organic compounds

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ISSN: 2414-3146

Volume 1| Part 3| March 2016| x160325

doi:10.1107/S2414314616003254

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4-Bromo-2-hydroxybenzoic acid

P. A. Suchetan,^a V. Suneetha,^b S. Naveen,^c N. K. Lokanath ^d and P. Krishna Murthy ^b ^*

^aDepartment of Chemistry, University College of Science, Tumkur University, Tumkur 572 103, India, ^bDepartment of Chemistry, Bapatla Engineering College (Autonomous), Bapatla 522 101, A.P., India, ^cInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru-6, India, and ^dDepartment of Physics, University of Mysore, Manasagangotri, Mysuru-6, India
^*Correspondence e-mail: krishnamurthypotla@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 21 February 2016; accepted 25 February 2016; online 11 March 2016)

In the title compound, C₇H₅BrO₃, the dihedral angle between the aromatic ring and the carboxylic acid group is 4.8 (4)°, and an intramolecular O—H⋯O hydrogen bond closes an S(6) ring. In the crystal, carboxylic acid inversion dimers linked by pairs of O—H⋯O hydrogen bonds generate R₂²(8) loops. Short Br⋯Br contacts [3.4442 (5) Å] between the molecules of the adjacent dimers leads to a one-dimensional architecture.

Keywords: crystal structure; O—H⋯O hydrogen bonds; Br⋯Br contacts; $[R_{2}^{2}]$ (8) dimers.

CCDC reference: 1455826

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Chemical scheme

Structure description

Derivatives of salicylic acid have many biological effects, such as anti-malarial (Fritzson et al., 2011 ), antifungal (Bassoli et al., 2008 ) and herbicidal activities (Silverman et al., 2005 ). As part of our studies in this area, the crystal structure of the title compound was studied.

The title molecule (I) is almost planar (r.m.s. deviation for the non-H atoms = 0.035 Å) and an intramolecular O—H⋯O hydrogen bond closes an S(6) ring (Fig. 1 and Table 1). The plane defined by the non-H atoms of the carboxyl group is twisted slightly by 4.8 (4)° to the mean plane of the phenyl ring. In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds generate $[R_{2}^{2}]$ (8) loops. Short Br⋯Br contacts [3.4442 (5) Å] between the molecules of the adjacent $[R_{2}^{2}]$ (8) dimers leads to a one-dimensional architecture (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯O1	0.84 (3)	1.80 (4)	2.572 (3)	152 (3)
O2—H1O2⋯O1ⁱ	0.83 (3)	1.88 (3)	2.697 (3)	170 (5)
Symmetry code: (i) -x, -y+3, -z+2.

Figure 1
A view of the molecular structure of the compound, showing displacement ellipsoids drawn at the 50% probability level. The intramolecular O—H⋯O hydrogen bond is shown as a thin dashed line.

Figure 2
Crystal packing of the title compound, displaying $[R_{2}^{2}]$ (8) O—H⋯O dimers and short Br⋯Br contacts.

The crystal structure of an isomer of the title molecule, 3-bromo-2-hydroxybenzoic acid (II) has been reported recently (Laus et al., 2015 ). The molecule of (II) is essentially planar and exhibits an intramolecular O—H⋯O hydrogen bond with the graph set motif S(6), similar to that observed in (I). Furthermore, in (II) the plane defined by the non-H atoms of the carboxyl group is twisted by an angle of 4.7 (4)° to the mean plane of the phenyl ring, which is almost same as that in (I). However, the crystal structures of the two compounds are very different in terms of the weak interactions displayed in them. Both the structures feature a pair of strong O—H⋯O hydrogen bonds generating $[R_{2}^{2}]$ (8) loops in the initial stage of packing, but both differ in the second stage of packing. In (I), short Br⋯Br contacts between the $[R_{2}^{2}]$ (8) loops leads to a one-dimensional architecture, whereas in (II), C—H⋯O interactions between the $[R_{2}^{2}]$ (8) loops leads into corrugated sheets which lie parallel to the (10 $[\overline{3}]$ ) plane.

Synthesis and crystallization

The title compound was purchased from Sigma Aldrich. Colourless prisms were recrystallized from a methanol: chloroform (2:1) solvent mixture.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₇H₅BrO₃
M_r	217.02
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	173
a, b, c (Å)	3.9283 (4), 5.9578 (6), 15.1246 (14)
α, β, γ (°)	92.925 (3), 90.620 (4), 94.710 (4)
V (Å³)	352.28 (6)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	7.58
Crystal size (mm)	0.28 × 0.24 × 0.19

Data collection
Diffractometer	Bruker APEXII
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.180, 0.237
No. of measured, independent and observed [I > 2σ(I)] reflections	3366, 1149, 1119
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.586

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.081, 1.09
No. of reflections	1149
No. of parameters	108
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.60
Computer programs: APEX2 (Bruker, 2009), SAINT-Plus (Bruker, 2009), SAINT-Plus (Bruker, 2009), SHELXS97 (Sheldrick, 2008 ), SHELXL97 (Sheldrick, 2015 ), Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1455826

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616003254/hb4022sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616003254/hb4022Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616003254/hb4022Isup3.cml

checkCIF report

Introduction top

Derivatives of salicylic acids are of great biological importance (Jack et al., 1997). The salicylic acid derivatives exhibits antioxidant, antiproliferative (Al-Dabbas et al., 2006), cytotoxic activities (Djurendic et al., 2011), anti-inflammatory (Delgado-Rivera et al., 2010) and anti-thrombotic activities (Zavodnik et al., 2009). Further, these derivatives have been studied for anti-malarial (Fritzson et al., 2011), antifungal (Bassoli et al., 2008) and herbicidal activities (Silverman et al., 2005). In view of the above fact, the crystal structure of the title compound was studied.

Experimental top

Synthesis and crystallization top

The title compound was purchased from Sigma Aldrich. Single crystals suitable for X-ray diffraction studies were obtained by solvent evaporation technique using methanol:chloroform (2:1) as the solvent mixture.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. Positions of hydrogen atoms bonded to carbon atoms were generated in idealized geometries using a riding model with C—H = 0.95 Å and their displacement parameters were set to U_iso(H) = 1.2 U_eq(C). The H atoms attached to O were identified from difference Fourier maps and their positions refined with restrained distances [O—H = 0.86 (2) Å] and their isotropic thermal displacement parameters were refined freely.

Experimental top

The title compound was purchased from Sigma Aldrich. Colourless prisms were recrystallized from a methanol: chloroform (2:1) solvent mixture.

Structure description top

Derivatives of salicylic acid have many biological effects, such as anti-malarial (Fritzson et al., 2011), antifungal (Bassoli et al., 2008) and herbicidal activities (Silverman et al., 2005). As part of our studies in this area, the crystal structure of the title compound was studied.

The title molecule (I) is almost planar (r.m.s. deviation for the non-H atoms = 0.035 Å) and an intramolecular O—H···O hydrogen bond closes an S(6) ring (Fig. 1 and Table 1). The plane defined by the non-H atoms of the carboxyl group is twisted slightly by 4.8 (4)° to the mean plane of the phenyl ring. In the crystal, inversion dimers linked by pairs of O—H···O hydrogen bonds generate R₂²(8) loops. Short Br···Br contacts [3.4442 (5) Å] between the molecules of the adjacent R₂²(8) dimers leads to a one-dimensional architecture (Fig. 2).

The crystal structure of an isomer of the title molecule, 3-bromo-2-hydroxybenzoic acid (II) has been reported recently (Laus et al., 2015). The molecule of (II) is essentially planar and exhibits an intramolecular O—H···O hydrogen bond with the graph set motif S(6), similar to that observed in (I). Furthermore, in (II) the plane defined by the non-H atoms of the carboxyl group is twisted by an angle of 4.7 (4)° to the mean plane of the phenyl ring, which is almost same as that in (I). However, the crystal structures of the two compounds are very different in terms of the weak interactions displayed in them. Both the structures feature a pair of strong O—H···O hydrogen bonds generating R₂²(8) loops in the initial stage of packing, but both differ in the second stage of packing. In (I), short Br···Br contacts between the R₂²(8) loops leads to a one-dimensional architecture, whereas in (II), C—H···O interactions between the R₂²(8) loops leads into corrugated sheets which lie parallel to the (103) plane.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2015).

Figures top

	Fig. 1. A view of the molecular structure of the compound, showing displacement ellipsoids drawn at the 50% probability level. The intramolecular O—H···O hydrogen bond is shown as a thin dashed line.
	Fig. 2. Crystal packing of the title compound, displaying R₂²(8) O—H···O dimers and short Br···Br contacts.

4-Bromo-2-hydroxybenzoic acid top

Crystal data top

C₇H₅BrO₃	F(000) = 212
M_r = 217.02	Prism
Triclinic, P1	D_x = 2.046 Mg m⁻³
Hall symbol: -P 1	Melting point: 490 K
a = 3.9283 (4) Å	Cu Kα radiation, λ = 1.54178 Å
b = 5.9578 (6) Å	Cell parameters from 112 reflections
c = 15.1246 (14) Å	θ = 5.9–64.6°
α = 92.925 (3)°	µ = 7.58 mm⁻¹
β = 90.620 (4)°	T = 173 K
γ = 94.710 (4)°	Prism, colourless
V = 352.28 (6) Å³	0.28 × 0.24 × 0.19 mm
Z = 2

Data collection top

Bruker APEXII diffractometer	1119 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.037
Graphite monochromator	θ_max = 64.6°, θ_min = 5.9°
phi and φ scans	h = −4→4
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −6→6
T_min = 0.180, T_max = 0.237	l = −17→17
3366 measured reflections	1 standard reflections every 1 reflections
1149 independent reflections	intensity decay: 0.1%

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.058P)² + 0.1123P] where P = (F_o² + 2F_c²)/3
1149 reflections	(Δ/σ)_max = 0.001
108 parameters	Δρ_max = 0.70 e Å⁻³
2 restraints	Δρ_min = −0.60 e Å⁻³

Crystal data top

C₇H₅BrO₃	γ = 94.710 (4)°
M_r = 217.02	V = 352.28 (6) Å³
Triclinic, P1	Z = 2
a = 3.9283 (4) Å	Cu Kα radiation
b = 5.9578 (6) Å	µ = 7.58 mm⁻¹
c = 15.1246 (14) Å	T = 173 K
α = 92.925 (3)°	0.28 × 0.24 × 0.19 mm
β = 90.620 (4)°

Data collection top

Bruker APEXII diffractometer	1119 reflections with I > 2σ(I)
Absorption correction: multi-scan (SADABS; Bruker, 2009)	R_int = 0.037
T_min = 0.180, T_max = 0.237	1 standard reflections every 1 reflections
3366 measured reflections	intensity decay: 0.1%
1149 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	2 restraints
wR(F²) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.70 e Å⁻³
1149 reflections	Δρ_min = −0.60 e Å⁻³
108 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
H1O3	0.330 (10)	1.016 (6)	0.938 (2)	0.029 (10)*
H1O2	−0.148 (12)	1.569 (7)	0.923 (2)	0.036 (12)*
Br1	0.36435 (6)	0.71828 (4)	0.566042 (18)	0.0210 (2)
O3	0.4036 (6)	0.9200 (4)	0.90163 (15)	0.0242 (5)
C7	0.0619 (8)	1.3240 (6)	0.8902 (2)	0.0182 (7)
O1	0.1583 (6)	1.2807 (4)	0.96509 (16)	0.0230 (5)
O2	−0.1112 (5)	1.4975 (3)	0.87610 (14)	0.0206 (4)
C5	0.0491 (7)	1.2401 (5)	0.7258 (2)	0.0170 (6)
H5	−0.0582	1.3752	0.7181	0.020*
C2	0.3665 (7)	0.8453 (5)	0.7487 (2)	0.0178 (6)
H2	0.4733	0.7098	0.7557	0.021*
C1	0.2746 (7)	0.9071 (4)	0.66562 (19)	0.0163 (6)
C4	0.1362 (7)	1.1832 (5)	0.8118 (2)	0.0156 (6)
C3	0.3011 (7)	0.9835 (5)	0.8217 (2)	0.0166 (6)
C6	0.1153 (7)	1.1055 (5)	0.6529 (2)	0.0162 (6)
H6	0.0548	1.1456	0.5951	0.019*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0278 (3)	0.0190 (3)	0.0160 (3)	0.00474 (15)	0.00193 (15)	−0.00593 (15)
O3	0.0340 (11)	0.0260 (11)	0.0137 (11)	0.0098 (9)	−0.0028 (9)	0.0009 (9)
C7	0.0187 (14)	0.0186 (14)	0.0163 (16)	−0.0040 (11)	0.0019 (12)	−0.0011 (12)
O1	0.0326 (12)	0.0250 (11)	0.0119 (12)	0.0067 (9)	−0.0022 (9)	−0.0017 (8)
O2	0.0320 (11)	0.0163 (10)	0.0133 (10)	0.0051 (8)	−0.0009 (8)	−0.0049 (8)
C5	0.0194 (13)	0.0134 (13)	0.0177 (15)	−0.0015 (10)	0.0014 (11)	−0.0010 (11)
C2	0.0178 (13)	0.0166 (13)	0.0188 (15)	0.0004 (10)	−0.0002 (11)	−0.0009 (11)
C1	0.0184 (13)	0.0149 (13)	0.0148 (14)	−0.0017 (10)	0.0015 (11)	−0.0025 (11)
C4	0.0171 (13)	0.0153 (13)	0.0137 (14)	−0.0016 (10)	−0.0014 (11)	−0.0009 (11)
C3	0.0165 (12)	0.0167 (13)	0.0163 (14)	−0.0006 (10)	−0.0002 (11)	0.0015 (11)
C6	0.0225 (13)	0.0161 (13)	0.0098 (13)	0.0008 (10)	−0.0008 (11)	−0.0011 (11)

Geometric parameters (Å, º) top

Br1—C1	1.887 (3)	C5—C4	1.406 (4)
O3—C3	1.353 (4)	C5—H5	0.9500
O3—H1O3	0.85 (2)	C2—C1	1.380 (4)
C7—O1	1.237 (4)	C2—C3	1.382 (5)
C7—O2	1.308 (4)	C2—H2	0.9500
C7—C4	1.464 (5)	C1—C6	1.403 (4)
O2—H1O2	0.83 (2)	C4—C3	1.414 (4)
C5—C6	1.370 (5)	C6—H6	0.9500

C3—O3—H1O3	104 (3)	C2—C1—Br1	119.0 (2)
O1—C7—O2	122.3 (3)	C6—C1—Br1	119.0 (2)
O1—C7—C4	121.7 (3)	C5—C4—C3	118.3 (3)
O2—C7—C4	116.0 (3)	C5—C4—C7	122.0 (3)
C7—O2—H1O2	111 (3)	C3—C4—C7	119.7 (3)
C6—C5—C4	121.6 (3)	O3—C3—C2	117.1 (2)
C6—C5—H5	119.2	O3—C3—C4	122.2 (3)
C4—C5—H5	119.2	C2—C3—C4	120.7 (3)
C1—C2—C3	119.0 (3)	C5—C6—C1	118.4 (3)
C1—C2—H2	120.5	C5—C6—H6	120.8
C3—C2—H2	120.5	C1—C6—H6	120.8
C2—C1—C6	122.0 (3)

C3—C2—C1—C6	−0.3 (4)	C1—C2—C3—C4	1.3 (4)
C3—C2—C1—Br1	180.0 (2)	C5—C4—C3—O3	177.8 (2)
C6—C5—C4—C3	1.1 (4)	C7—C4—C3—O3	−2.1 (4)
C6—C5—C4—C7	−179.0 (3)	C5—C4—C3—C2	−1.6 (4)
O1—C7—C4—C5	−175.3 (3)	C7—C4—C3—C2	178.5 (3)
O2—C7—C4—C5	4.6 (4)	C4—C5—C6—C1	−0.2 (4)
O1—C7—C4—C3	4.5 (5)	C2—C1—C6—C5	−0.3 (4)
O2—C7—C4—C3	−175.6 (3)	Br1—C1—C6—C5	179.5 (2)
C1—C2—C3—O3	−178.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···O1	0.84 (3)	1.80 (4)	2.572 (3)	152 (3)
O2—H1O2···O1ⁱ	0.83 (3)	1.88 (3)	2.697 (3)	170 (5)

Symmetry code: (i) −x, −y+3, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···O1	0.84 (3)	1.80 (4)	2.572 (3)	152 (3)
O2—H1O2···O1ⁱ	0.83 (3)	1.88 (3)	2.697 (3)	170 (5)

Symmetry code: (i) −x, −y+3, −z+2.

Experimental details

Crystal data
Chemical formula	C₇H₅BrO₃
M_r	217.02
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	3.9283 (4), 5.9578 (6), 15.1246 (14)
α, β, γ (°)	92.925 (3), 90.620 (4), 94.710 (4)
V (Å³)	352.28 (6)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	7.58
Crystal size (mm)	0.28 × 0.24 × 0.19

Data collection
Diffractometer	Bruker APEXII
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.180, 0.237
No. of measured, independent and observed [I > 2σ(I)] reflections	3366, 1149, 1119
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.586

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.081, 1.09
No. of reflections	1149
No. of parameters	108
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.60

Computer programs: APEX2 (Bruker, 2009), SAINT-Plus (Bruker, 2009), SAINT-Plus (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2015), Mercury (Macrae et al., 2008).

Acknowledgements

The authors are thankful to the Institution of Excellence, Vijnana Bhavana, University of Mysore, Mysore, for providing the single-crystal X-ray diffraction data.

References

Bassoli, A., Borgonovo, G., Caimi, S., Farina, G. & Moretti, M. (2008). Open Nat. Prod. J. 1, 14–19. CrossRef CAS Google Scholar
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Fritzson, I., Bedingfield, P. T. P., Sundin, A. P., McConkey, G. & Nilsson, U. J. (2011). Med. Chem. Commun. 2, 895–898. Web of Science CrossRef CAS Google Scholar
Laus, G., Kahlenberg, V., Gelbrich, T., Nerdinger, S. & Schottenberger, H. (2015). Acta Cryst. E71, 531–535. Web of Science CSD CrossRef IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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4-Bromo-2-hy­dr­oxy­benzoic acid

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

4-Bromo-2-hydroxybenzoic acid