2-(2,4-Di­hydroxy­benzoyl)­benzoic acid

Li, Y.; Ge, F.-Y.; Chen, L.-G.; Dong, C.-M.; Yan, X.-L.; Duan, E.-H.; Zeng, T.; Zhang, Y.-C.; Bai, G.-Y.

doi:10.1107/S1600536805014844

2-(2,4-Dihydroxybenzoyl)benzoic acid

Y. Li, F.-Y. Ge, L.-G. Chen, C.-M. Dong, X.-L. Yan, E.-H. Duan, T. Zeng, Y.-C. Zhang and G.-Y. Bai

In the title structure, C₁₄H₁₀O₅, the angle between the planes formed by the 2,4-dihydroxybenzoyl and o-benzoic acid moieties is 87.12 (4)°. In addition to an intramolecular O—H

O hydrogen bond, intermolecular O—H

O hydrogen bonds (H

O = 1.76 and 1.89 Å) connect molecules to form a two-dimensional network parallel to (10 $\overline 1$ ).

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805014844/lh6413sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805014844/lh6413Isup2.hkl Contains datablock I

CCDC reference: 274575

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Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.003 Å
R factor = 0.049
wR factor = 0.146
Data-to-parameter ratio = 14.3

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No errors found in this datablock

Computing details top

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

2-(2,4-Dihydroxybenzoyl)benzoic acid top

Crystal data top

C₁₄H₁₀O₅	F(000) = 536
M_r = 258.22	D_x = 1.365 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 474 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.331 (3) Å	Cell parameters from 2633 reflections
b = 11.628 (4) Å	θ = 2.6–26.5°
c = 11.640 (4) Å	µ = 0.11 mm⁻¹
β = 116.034 (5)°	T = 294 K
V = 1256.4 (7) Å³	Block, colourless
Z = 4	0.30 × 0.22 × 0.22 mm

Data collection top

Bruker SMART CCD diffractometer	2626 independent reflections
Radiation source: fine-focus sealed tube	1762 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.099
φ and ω scans	θ_max = 26.7°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −12→12
T_min = 0.963, T_max = 0.977	k = −13→14
6755 measured reflections	l = −14→13

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0478P)² + 0.3516P] where P = (F_o² + 2F_c²)/3
2626 reflections	(Δ/σ)_max < 0.001
184 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

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
O1	0.28344 (15)	0.31036 (16)	0.44868 (15)	0.0581 (5)
O2	0.51504 (16)	0.2925 (2)	0.49583 (19)	0.0746 (6)
H2	0.516 (3)	0.250 (3)	0.560 (3)	0.087 (10)*
O3	0.01604 (15)	0.33945 (15)	0.18108 (15)	0.0572 (5)
O4	−0.17529 (15)	0.41733 (17)	0.25016 (16)	0.0608 (5)
H4	−0.134 (3)	0.369 (3)	0.216 (3)	0.088 (10)*
O5	−0.0508 (2)	0.75316 (16)	0.5080 (2)	0.0746 (6)
H5	−0.132 (4)	0.733 (3)	0.511 (3)	0.103 (11)*
C1	0.3836 (2)	0.32926 (19)	0.42363 (19)	0.0426 (5)
C2	0.3694 (2)	0.39474 (18)	0.30884 (18)	0.0400 (5)
C3	0.23439 (19)	0.43702 (18)	0.22257 (17)	0.0388 (5)
C4	0.2224 (2)	0.4955 (2)	0.1141 (2)	0.0516 (6)
H4A	0.1331	0.5235	0.0563	0.062*
C5	0.3419 (2)	0.5127 (2)	0.0909 (2)	0.0547 (6)
H5A	0.3322	0.5515	0.0177	0.066*
C6	0.4747 (2)	0.4722 (2)	0.1764 (2)	0.0556 (6)
H6	0.5550	0.4846	0.1616	0.067*
C7	0.4888 (2)	0.4131 (2)	0.2845 (2)	0.0499 (6)
H7	0.5786	0.3853	0.3415	0.060*
C8	0.09718 (19)	0.42241 (18)	0.23772 (18)	0.0401 (5)
C9	0.05604 (18)	0.50795 (18)	0.30447 (18)	0.0393 (5)
C10	−0.07981 (19)	0.50272 (19)	0.30834 (19)	0.0433 (5)
C11	−0.1173 (2)	0.5859 (2)	0.3735 (2)	0.0498 (6)
H11	−0.2072	0.5832	0.3736	0.060*
C12	−0.0219 (2)	0.67262 (19)	0.4384 (2)	0.0517 (6)
C13	0.1129 (2)	0.6803 (2)	0.4358 (2)	0.0539 (6)
H13	0.1765	0.7395	0.4784	0.065*
C14	0.1485 (2)	0.59974 (19)	0.3700 (2)	0.0458 (5)
H14	0.2373	0.6053	0.3681	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0417 (8)	0.0787 (12)	0.0642 (10)	0.0093 (8)	0.0327 (7)	0.0198 (9)
O2	0.0337 (8)	0.1151 (17)	0.0712 (11)	0.0076 (9)	0.0195 (8)	0.0453 (12)
O3	0.0420 (8)	0.0741 (11)	0.0604 (9)	−0.0141 (8)	0.0269 (7)	−0.0225 (9)
O4	0.0333 (8)	0.0822 (13)	0.0688 (11)	−0.0122 (8)	0.0241 (8)	−0.0166 (10)
O5	0.0871 (13)	0.0554 (11)	0.1157 (17)	−0.0002 (10)	0.0762 (13)	−0.0117 (10)
C1	0.0318 (10)	0.0511 (13)	0.0438 (11)	0.0005 (9)	0.0157 (8)	0.0027 (10)
C2	0.0350 (10)	0.0454 (11)	0.0407 (10)	−0.0005 (8)	0.0176 (8)	0.0007 (9)
C3	0.0331 (9)	0.0457 (11)	0.0399 (10)	0.0005 (8)	0.0182 (8)	−0.0023 (9)
C4	0.0394 (10)	0.0645 (15)	0.0489 (12)	0.0053 (10)	0.0177 (9)	0.0109 (11)
C5	0.0543 (12)	0.0654 (15)	0.0511 (12)	0.0005 (12)	0.0294 (10)	0.0145 (12)
C6	0.0459 (12)	0.0698 (16)	0.0641 (14)	−0.0043 (11)	0.0362 (11)	0.0060 (12)
C7	0.0332 (10)	0.0647 (15)	0.0547 (13)	0.0034 (10)	0.0221 (9)	0.0064 (11)
C8	0.0288 (9)	0.0530 (13)	0.0359 (10)	−0.0024 (9)	0.0118 (8)	−0.0012 (9)
C9	0.0283 (9)	0.0490 (12)	0.0397 (10)	0.0039 (8)	0.0141 (8)	0.0042 (9)
C10	0.0289 (9)	0.0562 (13)	0.0435 (11)	0.0019 (9)	0.0146 (8)	0.0057 (10)
C11	0.0367 (11)	0.0591 (14)	0.0619 (13)	0.0084 (10)	0.0295 (10)	0.0087 (12)
C12	0.0570 (13)	0.0448 (12)	0.0676 (14)	0.0100 (11)	0.0406 (12)	0.0064 (11)
C13	0.0525 (13)	0.0459 (12)	0.0738 (15)	−0.0039 (10)	0.0374 (12)	−0.0047 (11)
C14	0.0341 (10)	0.0505 (12)	0.0587 (13)	0.0003 (9)	0.0256 (9)	0.0017 (10)

Geometric parameters (Å, º) top

O1—C1	1.212 (2)	C5—C6	1.377 (3)
O2—C1	1.316 (2)	C5—H5A	0.9300
O2—H2	0.89 (3)	C6—C7	1.384 (3)
O3—C8	1.258 (2)	C6—H6	0.9300
O4—C10	1.353 (3)	C7—H7	0.9300
O4—H4	0.90 (3)	C8—C9	1.436 (3)
O5—C12	1.355 (3)	C9—C14	1.412 (3)
O5—H5	0.89 (4)	C9—C10	1.425 (3)
C1—C2	1.488 (3)	C10—C11	1.385 (3)
C2—C7	1.398 (3)	C11—C12	1.381 (3)
C2—C3	1.402 (3)	C11—H11	0.9300
C3—C4	1.391 (3)	C12—C13	1.409 (3)
C3—C8	1.513 (3)	C13—C14	1.359 (3)
C4—C5	1.389 (3)	C13—H13	0.9300
C4—H4A	0.9300	C14—H14	0.9300

C1—O2—H2	110 (2)	C2—C7—H7	119.7
C10—O4—H4	107 (2)	O3—C8—C9	121.81 (17)
C12—O5—H5	107 (2)	O3—C8—C3	117.90 (17)
O1—C1—O2	122.6 (2)	C9—C8—C3	120.01 (17)
O1—C1—C2	123.41 (18)	C14—C9—C10	117.20 (18)
O2—C1—C2	114.02 (17)	C14—C9—C8	121.67 (17)
C7—C2—C3	119.36 (18)	C10—C9—C8	121.12 (18)
C7—C2—C1	120.81 (18)	O4—C10—C11	117.94 (17)
C3—C2—C1	119.83 (17)	O4—C10—C9	121.81 (19)
C4—C3—C2	119.06 (17)	C11—C10—C9	120.24 (19)
C4—C3—C8	116.49 (17)	C12—C11—C10	120.34 (18)
C2—C3—C8	124.45 (17)	C12—C11—H11	119.8
C5—C4—C3	120.96 (19)	C10—C11—H11	119.8
C5—C4—H4A	119.5	O5—C12—C11	122.7 (2)
C3—C4—H4A	119.5	O5—C12—C13	116.6 (2)
C6—C5—C4	119.9 (2)	C11—C12—C13	120.7 (2)
C6—C5—H5A	120.1	C14—C13—C12	118.8 (2)
C4—C5—H5A	120.1	C14—C13—H13	120.6
C5—C6—C7	120.08 (19)	C12—C13—H13	120.6
C5—C6—H6	120.0	C13—C14—C9	122.67 (19)
C7—C6—H6	120.0	C13—C14—H14	118.7
C6—C7—C2	120.66 (19)	C9—C14—H14	118.7
C6—C7—H7	119.7

O1—C1—C2—C7	−179.5 (2)	C2—C3—C8—C9	90.8 (3)
O2—C1—C2—C7	0.0 (3)	O3—C8—C9—C14	178.77 (19)
O1—C1—C2—C3	−0.7 (3)	C3—C8—C9—C14	−7.5 (3)
O2—C1—C2—C3	178.9 (2)	O3—C8—C9—C10	−0.5 (3)
C7—C2—C3—C4	0.5 (3)	C3—C8—C9—C10	173.21 (17)
C1—C2—C3—C4	−178.38 (19)	C14—C9—C10—O4	−179.06 (18)
C7—C2—C3—C8	179.7 (2)	C8—C9—C10—O4	0.3 (3)
C1—C2—C3—C8	0.8 (3)	C14—C9—C10—C11	0.5 (3)
C2—C3—C4—C5	−0.3 (3)	C8—C9—C10—C11	179.82 (19)
C8—C3—C4—C5	−179.5 (2)	O4—C10—C11—C12	177.71 (19)
C3—C4—C5—C6	−0.5 (4)	C9—C10—C11—C12	−1.9 (3)
C4—C5—C6—C7	0.9 (4)	C10—C11—C12—O5	−177.2 (2)
C5—C6—C7—C2	−0.6 (4)	C10—C11—C12—C13	2.1 (3)
C3—C2—C7—C6	−0.1 (3)	O5—C12—C13—C14	178.3 (2)
C1—C2—C7—C6	178.8 (2)	C11—C12—C13—C14	−1.0 (3)
C4—C3—C8—O3	84.0 (3)	C12—C13—C14—C9	−0.4 (3)
C2—C3—C8—O3	−95.2 (2)	C10—C9—C14—C13	0.6 (3)
C4—C3—C8—C9	−90.0 (2)	C8—C9—C14—C13	−178.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.89 (3)	1.76 (3)	2.643 (2)	177 (3)
O4—H4···O3	0.90 (3)	1.80 (3)	2.602 (2)	148 (3)
O5—H5···O1ⁱⁱ	0.89 (4)	1.89 (4)	2.764 (2)	169 (3)

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

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2-(2,4-Di­hydroxy­benzoyl)­benzoic acid

Supporting information

Key indicators

checkCIF/PLATON results

2-(2,4-Dihydroxybenzoyl)benzoic acid