5-Bromo­salicylic acid

The title compound, C₇H₅BrO₃, crystallizes with two independent mol­ecules in the asymmetric unit. All the O atoms in the two mol­ecules contribute to the formation of a three-dimensional hydrogen-bonded network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.048
• wR factor = 0.111
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(I)

Crystal data

C7H5BrO3	Z = 4
Mr = 217.02	F(000) = 424
Triclinic, P1	Dx = 1.904 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.805 (1) Å	Cell parameters from 2884 reflections
b = 12.047 (2) Å	θ = 6–27.5°
c = 14.666 (3) Å	µ = 5.38 mm^−1
α = 114.06 (3)°	T = 293 K
β = 90.40 (3)°	Needle, colorless
γ = 101.19 (3)°	0.14 × 0.06 × 0.05 mm
V = 756.9 (3) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	2884 independent reflections
Radiation source: fine-focus sealed tube	1786 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.514, Tmax = 0.767	k = −14→14
5095 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 0.95	w = 1/[σ^2(Fo^2) + (0.0474P)^2] where P = (Fo^2 + 2Fc^2)/3
2884 reflections	(Δ/σ)max = 0.003
199 parameters	Δρmax = 0.52 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.25119 (15)	0.48915 (6)	1.17770 (5)	0.0856 (3)
Br2	1.18701 (11)	0.81837 (5)	0.36237 (4)	0.0617 (2)
C1	0.5842 (9)	0.1934 (5)	0.9862 (4)	0.0453 (12)
C2	0.4840 (10)	0.1796 (5)	0.8913 (4)	0.0517 (13)
C3	0.3207 (11)	0.2593 (5)	0.8842 (4)	0.0569 (14)
H3A	0.2526	0.2495	0.8191	0.080*
C4	0.2555 (12)	0.3509 (5)	0.9682 (5)	0.0631 (15)
H4A	0.1427	0.4059	0.9627	0.080*
C5	0.3520 (11)	0.3630 (5)	1.0618 (4)	0.0539 (13)
C6	0.5135 (10)	0.2875 (5)	1.0717 (4)	0.0520 (13)
H6A	0.5801	0.2982	1.1372	0.080*
C7	0.7631 (10)	0.1111 (5)	0.9956 (4)	0.0527 (13)
C8	0.6147 (9)	0.7144 (4)	0.5390 (4)	0.0425 (12)
C9	0.7277 (11)	0.7988 (5)	0.6366 (4)	0.0478 (12)
C10	0.9752 (11)	0.8867 (5)	0.6504 (4)	0.0543 (14)
H10A	1.0527	0.9449	0.7171	0.080*
C11	1.1106 (11)	0.8911 (5)	0.5699 (4)	0.0523 (13)
H11A	1.2839	0.9517	0.5800	0.080*
C12	0.9997 (10)	0.8090 (5)	0.4732 (4)	0.0458 (12)
C13	0.7562 (10)	0.7204 (4)	0.4573 (4)	0.0429 (12)
H13A	0.6814	0.6627	0.3901	0.080*
C14	0.3498 (10)	0.6208 (4)	0.5223 (4)	0.0415 (11)
O1	0.8472 (8)	0.1329 (3)	1.0875 (3)	0.0646 (10)
H1A	0.9495	0.0820	1.0857	0.080*
O2	0.8317 (8)	0.0295 (4)	0.9219 (3)	0.0626 (10)
O3	0.5389 (8)	0.0905 (4)	0.8053 (3)	0.0647 (10)
H3B	0.6431	0.0485	0.8187	0.080*
O4	0.2719 (7)	0.5438 (3)	0.4282 (2)	0.0548 (9)
H4B	0.1153	0.4942	0.4244	0.080*
O5	0.2157 (7)	0.6147 (3)	0.5919 (3)	0.0535 (9)
O6	0.6054 (8)	0.8009 (3)	0.7193 (3)	0.0674 (11)
H6C	0.4536	0.7446	0.7026	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0976 (5)	0.0739 (5)	0.0734 (5)	0.0245 (4)	0.0197 (4)	0.0159 (4)
Br2	0.0565 (4)	0.0695 (4)	0.0670 (4)	0.0087 (3)	0.0087 (3)	0.0383 (3)
C1	0.039 (3)	0.051 (3)	0.044 (3)	−0.001 (2)	0.003 (2)	0.023 (3)
C2	0.043 (3)	0.052 (3)	0.051 (3)	−0.002 (3)	−0.001 (2)	0.019 (3)
C3	0.059 (3)	0.057 (4)	0.054 (4)	0.006 (3)	−0.006 (3)	0.026 (3)
C4	0.065 (4)	0.058 (4)	0.072 (4)	0.011 (3)	0.002 (3)	0.035 (3)
C5	0.052 (3)	0.050 (3)	0.059 (4)	0.005 (3)	0.005 (3)	0.025 (3)
C6	0.052 (3)	0.058 (4)	0.049 (3)	0.003 (3)	0.002 (3)	0.029 (3)
C7	0.039 (3)	0.060 (4)	0.056 (4)	−0.007 (3)	−0.001 (3)	0.029 (3)
C8	0.038 (3)	0.038 (3)	0.052 (3)	0.012 (2)	−0.001 (2)	0.017 (3)
C9	0.050 (3)	0.043 (3)	0.045 (3)	0.008 (3)	−0.001 (2)	0.013 (3)
C10	0.050 (3)	0.048 (3)	0.051 (3)	0.002 (3)	−0.003 (3)	0.010 (3)
C11	0.047 (3)	0.039 (3)	0.064 (4)	0.001 (2)	−0.004 (3)	0.018 (3)
C12	0.043 (3)	0.047 (3)	0.052 (3)	0.012 (2)	0.003 (2)	0.023 (3)
C13	0.044 (3)	0.037 (3)	0.043 (3)	0.011 (2)	−0.002 (2)	0.011 (2)
C14	0.042 (3)	0.038 (3)	0.043 (3)	0.011 (2)	0.004 (2)	0.015 (3)
O1	0.074 (3)	0.075 (3)	0.055 (2)	0.026 (2)	0.0056 (19)	0.033 (2)
O2	0.067 (2)	0.062 (3)	0.053 (2)	0.015 (2)	−0.0026 (19)	0.019 (2)
O3	0.069 (2)	0.070 (3)	0.048 (2)	0.021 (2)	−0.0042 (18)	0.015 (2)
O4	0.049 (2)	0.053 (2)	0.048 (2)	−0.0019 (17)	0.0023 (16)	0.0119 (19)
O5	0.054 (2)	0.051 (2)	0.047 (2)	0.0015 (17)	0.0045 (17)	0.0165 (18)
O6	0.063 (2)	0.073 (3)	0.047 (2)	−0.005 (2)	0.0054 (18)	0.013 (2)

Geometric parameters (Å, º)

Br1—C5	1.904 (5)	C8—C13	1.403 (6)
Br2—C12	1.897 (5)	C8—C14	1.471 (6)
C1—C6	1.403 (7)	C9—O6	1.345 (6)
C1—C2	1.404 (7)	C9—C10	1.381 (7)
C1—C7	1.476 (7)	C10—C11	1.367 (7)
C2—O3	1.350 (6)	C10—H10A	0.9600
C2—C3	1.386 (7)	C11—C12	1.384 (7)
C3—C4	1.366 (7)	C11—H11A	0.9600
C3—H3A	0.9601	C12—C13	1.368 (7)
C4—C5	1.387 (7)	C13—H13A	0.9600
C4—H4A	0.9602	C14—O5	1.231 (5)
C5—C6	1.353 (7)	C14—O4	1.312 (5)
C6—H6A	0.9601	O1—H1A	0.8499
C7—O2	1.227 (6)	O3—H3B	0.8500
C7—O1	1.309 (6)	O4—H4B	0.8500
C8—C9	1.402 (6)	O6—H6C	0.8500
C6—C1—C2	118.7 (5)	C13—C8—C14	120.3 (4)
C6—C1—C7	120.9 (5)	O6—C9—C10	117.1 (4)
C2—C1—C7	120.5 (5)	O6—C9—C8	123.5 (5)
O3—C2—C3	118.0 (5)	C10—C9—C8	119.4 (5)
O3—C2—C1	122.5 (5)	C11—C10—C9	120.5 (5)
C3—C2—C1	119.5 (5)	C11—C10—H10A	119.8
C4—C3—C2	121.0 (5)	C9—C10—H10A	119.7
C4—C3—H3A	119.8	C10—C11—C12	120.5 (5)
C2—C3—H3A	119.2	C10—C11—H11A	120.1
C3—C4—C5	119.2 (5)	C12—C11—H11A	119.3
C3—C4—H4A	120.5	C13—C12—C11	120.3 (5)
C5—C4—H4A	120.2	C13—C12—Br2	119.8 (4)
C6—C5—C4	121.4 (5)	C11—C12—Br2	119.9 (4)
C6—C5—Br1	120.2 (4)	C12—C13—C8	119.9 (4)
C4—C5—Br1	118.4 (4)	C12—C13—H13A	120.0
C5—C6—C1	120.1 (5)	C8—C13—H13A	120.0
C5—C6—H6A	120.0	O5—C14—O4	123.0 (4)
C1—C6—H6A	119.8	O5—C14—C8	122.2 (5)
O2—C7—O1	122.6 (5)	O4—C14—C8	114.8 (4)
O2—C7—C1	122.0 (5)	C7—O1—H1A	108.8
O1—C7—C1	115.3 (5)	C2—O3—H3B	109.7
C9—C8—C13	119.3 (5)	C14—O4—H4B	109.4
C9—C8—C14	120.4 (5)	C9—O6—H6C	109.6
C6—C1—C2—O3	−179.1 (4)	C13—C8—C9—O6	179.3 (4)
C7—C1—C2—O3	1.6 (7)	C14—C8—C9—O6	−0.4 (7)
C6—C1—C2—C3	0.5 (7)	C13—C8—C9—C10	0.3 (7)
C7—C1—C2—C3	−178.8 (4)	C14—C8—C9—C10	−179.4 (4)
O3—C2—C3—C4	179.5 (5)	O6—C9—C10—C11	−179.4 (5)
C1—C2—C3—C4	−0.1 (8)	C8—C9—C10—C11	−0.4 (8)
C2—C3—C4—C5	−0.7 (8)	C9—C10—C11—C12	1.0 (8)
C3—C4—C5—C6	1.2 (8)	C10—C11—C12—C13	−1.5 (8)
C3—C4—C5—Br1	−178.7 (4)	C10—C11—C12—Br2	178.9 (4)
C4—C5—C6—C1	−0.8 (8)	C11—C12—C13—C8	1.4 (7)
Br1—C5—C6—C1	179.1 (3)	Br2—C12—C13—C8	−179.0 (3)
C2—C1—C6—C5	−0.1 (7)	C9—C8—C13—C12	−0.8 (7)
C7—C1—C6—C5	179.3 (4)	C14—C8—C13—C12	178.9 (4)
C6—C1—C7—O2	−178.8 (5)	C9—C8—C14—O5	1.6 (7)
C2—C1—C7—O2	0.5 (7)	C13—C8—C14—O5	−178.1 (4)
C6—C1—C7—O1	0.0 (7)	C9—C8—C14—O4	−177.2 (4)
C2—C1—C7—O1	179.3 (4)	C13—C8—C14—O4	3.1 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2^i	0.85	1.83	2.681 (5)	179
O3—H3B···O2	0.85	1.87	2.614 (5)	145
O4—H4B···O5^ii	0.85	1.80	2.648 (5)	177
O6—H6C···O5	0.85	1.90	2.633 (5)	144

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