4,4'-[(5-Carb-oxy-1,3-phenyl-ene)bis-(-oxy)]dibenzoic acid.

In the title compound, C(21)H(14)O(8), the central benzene ring makes dihedral angles of 77.8 (6) and 75.9 (5)° with the outer benzene rings. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds involving carboxyl groups, forming one-dimensional ladders. Two-dimensional layers are formed by inter-penetration of these one-dimensional ladders.

Related literature

For general background, see: Moulton & Zaworotko,(2001 ▶); Kitagawa et al.,(2001 ▶); Lee et al.,(2009 ▶); Robin & Fromm, (2006 ▶). For the preparation of title compound, see: Neogi et al.(2009 ▶). For related structa­res, see: Lama et al.(2010 ▶); Pan et al. (2007 ▶).

Experimental

Crystal data

C21H14O8

M = 394.32

Monoclinic,

a = 17.235 (3) Å

b = 13.419 (3) Å

c = 15.586 (3) Å

β = 96.24 (3)°

V = 3583.3 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.33 × 0.29 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.316, T max = 0.622

16922 measured reflections

4073 independent reflections

2862 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.121

S = 1.09

4073 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXP97 (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812012275/bq2343sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012275/bq2343Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012275/bq2343Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H14O8	F(000) = 1632
Mr = 394.32	Dx = 1.462 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4073 reflections
a = 17.235 (3) Å	θ = 3.0–27.5°
b = 13.419 (3) Å	µ = 0.11 mm−1
c = 15.586 (3) Å	T = 293 K
β = 96.24 (3)°	Block, colourless
V = 3583.3 (12) Å3	0.33 × 0.29 × 0.25 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	4073 independent reflections
Radiation source: fine-focus sealed tube	2862 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
phi and ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −22→22
Tmin = 0.316, Tmax = 0.622	k = −17→17
16922 measured reflections	l = −19→20

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0601P)2 + 0.3436P] where P = (Fo2 + 2Fc2)/3
4073 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.16748 (7)	0.89288 (12)	−0.11510 (7)	0.0630 (4)
O2	−0.07879 (6)	0.73896 (9)	−0.14922 (7)	0.0404 (3)
O3	−0.06065 (6)	0.88133 (11)	0.15033 (7)	0.0503 (4)
H6	−0.0624	0.8964	0.2011	0.080*
O4	0.06498 (6)	0.92236 (9)	0.18120 (7)	0.0386 (3)
O5	0.44526 (7)	1.12170 (10)	0.10342 (8)	0.0533 (3)
O6	0.48890 (7)	0.96517 (11)	0.10924 (10)	0.0622 (4)
H3	0.5260	0.9916	0.1379	0.080*
O7	−0.42509 (6)	0.81151 (10)	−0.31119 (8)	0.0517 (3)
H8	−0.4653	0.8389	−0.3320	0.080*
O8	−0.38899 (7)	0.96958 (10)	−0.28672 (8)	0.0510 (3)
C1	0.10101 (8)	0.87058 (14)	−0.07678 (10)	0.0383 (4)
C2	0.04339 (9)	0.82152 (13)	−0.12950 (10)	0.0389 (4)
H11A	0.0509	0.8057	−0.1861	0.080*
C3	−0.02518 (8)	0.79647 (12)	−0.09712 (10)	0.0335 (4)
C4	−0.03815 (8)	0.82052 (12)	−0.01343 (10)	0.0338 (4)
H9A	−0.0852	0.8047	0.0074	0.080*
C5	0.02053 (8)	0.86866 (12)	0.03845 (9)	0.0305 (3)
C6	0.09117 (8)	0.89385 (12)	0.00791 (9)	0.0340 (4)
H13A	0.1305	0.9254	0.0435	0.080*
C7	0.01100 (8)	0.89365 (12)	0.13006 (10)	0.0318 (3)
C8	0.23310 (9)	0.92824 (16)	−0.06384 (10)	0.0457 (5)
C9	0.24061 (9)	1.02836 (17)	−0.04567 (12)	0.0520 (5)
H3A	0.2011	1.0727	−0.0652	0.080*
C10	0.30817 (10)	1.06221 (15)	0.00240 (12)	0.0475 (4)
H2A	0.3139	1.1296	0.0154	0.080*
C11	0.36696 (8)	0.99590 (14)	0.03100 (10)	0.0379 (4)
C12	0.35866 (10)	0.89573 (15)	0.01005 (12)	0.0491 (5)
H6A	0.3984	0.8512	0.0282	0.080*
C13	0.29151 (10)	0.86173 (16)	−0.03783 (11)	0.0510 (5)
H5A	0.2860	0.7946	−0.0522	0.080*
C14	0.43795 (9)	1.03153 (14)	0.08419 (11)	0.0393 (4)
C15	−0.15218 (8)	0.77687 (12)	−0.17470 (9)	0.0310 (3)
C16	−0.20659 (9)	0.70800 (13)	−0.21092 (11)	0.0396 (4)
H17A	−0.1938	0.6408	−0.2131	0.080*
C17	−0.27973 (9)	0.74089 (13)	−0.24351 (11)	0.0407 (4)
H16A	−0.3166	0.6952	−0.2673	0.080*
C18	−0.29914 (8)	0.84138 (13)	−0.24126 (10)	0.0340 (4)
C19	−0.24389 (9)	0.90878 (13)	−0.20428 (10)	0.0380 (4)
H20A	−0.2565	0.9761	−0.2023	0.080*
C20	−0.17048 (9)	0.87698 (13)	−0.17049 (10)	0.0367 (4)
H19A	−0.1340	0.9223	−0.1453	0.080*
C21	−0.37538 (9)	0.87785 (13)	−0.28147 (10)	0.0376 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0313 (6)	0.1242 (13)	0.0339 (6)	−0.0307 (7)	0.0050 (5)	−0.0151 (7)
O2	0.0226 (5)	0.0450 (7)	0.0501 (7)	0.0008 (5)	−0.0117 (5)	−0.0106 (5)
O3	0.0275 (6)	0.0879 (10)	0.0359 (6)	−0.0055 (6)	0.0051 (5)	−0.0026 (6)
O4	0.0332 (6)	0.0474 (7)	0.0347 (6)	−0.0087 (5)	0.0009 (5)	−0.0024 (5)
O5	0.0394 (7)	0.0487 (9)	0.0676 (9)	−0.0075 (6)	−0.0131 (6)	−0.0023 (6)
O6	0.0382 (7)	0.0610 (10)	0.0805 (9)	0.0024 (7)	−0.0247 (6)	−0.0065 (7)
O7	0.0291 (6)	0.0479 (8)	0.0730 (9)	0.0008 (5)	−0.0179 (6)	−0.0011 (6)
O8	0.0401 (7)	0.0423 (8)	0.0657 (8)	0.0062 (6)	−0.0167 (6)	−0.0016 (6)
C1	0.0226 (7)	0.0587 (12)	0.0329 (8)	−0.0054 (7)	0.0002 (6)	0.0002 (8)
C2	0.0266 (8)	0.0567 (12)	0.0317 (8)	−0.0007 (7)	−0.0045 (6)	−0.0038 (7)
C3	0.0207 (7)	0.0385 (9)	0.0386 (8)	0.0009 (6)	−0.0088 (6)	−0.0009 (7)
C4	0.0215 (7)	0.0412 (10)	0.0378 (8)	−0.0012 (6)	−0.0016 (6)	0.0027 (7)
C5	0.0242 (7)	0.0348 (9)	0.0316 (7)	0.0010 (6)	−0.0014 (6)	0.0048 (6)
C6	0.0242 (7)	0.0442 (10)	0.0320 (8)	−0.0050 (7)	−0.0036 (6)	0.0010 (7)
C7	0.0254 (7)	0.0353 (9)	0.0340 (8)	0.0012 (6)	0.0000 (6)	0.0043 (6)
C8	0.0257 (8)	0.0812 (15)	0.0303 (8)	−0.0177 (9)	0.0038 (7)	−0.0046 (9)
C9	0.0272 (8)	0.0777 (15)	0.0488 (10)	0.0032 (9)	−0.0062 (7)	0.0007 (10)
C10	0.0311 (9)	0.0559 (12)	0.0537 (11)	−0.0020 (8)	−0.0039 (8)	−0.0007 (9)
C11	0.0259 (8)	0.0483 (11)	0.0383 (8)	−0.0064 (7)	−0.0018 (6)	0.0044 (8)
C12	0.0402 (9)	0.0508 (12)	0.0537 (11)	−0.0071 (8)	−0.0072 (8)	0.0019 (9)
C13	0.0452 (10)	0.0584 (13)	0.0481 (10)	−0.0179 (9)	−0.0011 (9)	−0.0028 (9)
C14	0.0264 (8)	0.0454 (11)	0.0444 (9)	−0.0010 (7)	−0.0031 (7)	0.0028 (8)
C15	0.0211 (7)	0.0401 (9)	0.0307 (7)	−0.0023 (6)	−0.0026 (6)	0.0010 (7)
C16	0.0287 (8)	0.0352 (10)	0.0518 (10)	−0.0024 (7)	−0.0098 (7)	−0.0023 (7)
C17	0.0260 (8)	0.0401 (10)	0.0526 (10)	−0.0063 (7)	−0.0106 (7)	−0.0001 (8)
C18	0.0246 (7)	0.0408 (10)	0.0353 (8)	−0.0009 (7)	−0.0033 (6)	0.0021 (7)
C19	0.0325 (8)	0.0379 (10)	0.0412 (9)	0.0015 (7)	−0.0065 (7)	0.0004 (7)
C20	0.0289 (8)	0.0396 (10)	0.0394 (8)	−0.0070 (7)	−0.0065 (7)	−0.0021 (7)
C21	0.0265 (8)	0.0438 (11)	0.0406 (9)	−0.0007 (7)	−0.0043 (7)	−0.0004 (7)

O1—C1	1.3811 (18)	C8—C13	1.373 (3)
O1—C8	1.395 (2)	C8—C9	1.376 (3)
O2—C15	1.3810 (17)	C9—C10	1.391 (2)
O2—C3	1.3949 (18)	C9—H3A	0.9300
O3—C7	1.3179 (17)	C10—C11	1.385 (2)
O3—H6	0.8200	C10—H2A	0.9300
O4—C7	1.2199 (19)	C11—C12	1.387 (3)
O5—C14	1.250 (2)	C11—C14	1.481 (2)
O6—C14	1.281 (2)	C12—C13	1.384 (2)
O6—H3	0.8200	C12—H6A	0.9300
O7—C21	1.286 (2)	C13—H5A	0.9300
O7—H8	0.8200	C15—C20	1.383 (2)
O8—C21	1.254 (2)	C15—C16	1.392 (2)
C1—C6	1.385 (2)	C16—C17	1.379 (2)
C1—C2	1.385 (2)	C16—H17A	0.9300
C2—C3	1.376 (2)	C17—C18	1.391 (2)
C2—H11A	0.9300	C17—H16A	0.9300
C3—C4	1.385 (2)	C18—C19	1.392 (2)
C4—C5	1.384 (2)	C18—C21	1.476 (2)
C4—H9A	0.9300	C19—C20	1.384 (2)
C5—C6	1.396 (2)	C19—H20A	0.9300
C5—C7	1.493 (2)	C20—H19A	0.9300
C6—H13A	0.9300
C1—O1—C8	119.01 (12)	C9—C10—H2A	119.9
C15—O2—C3	119.45 (12)	C10—C11—C12	119.59 (16)
C7—O3—H6	109.5	C10—C11—C14	120.24 (17)
C14—O6—H3	109.5	C12—C11—C14	120.17 (15)
C21—O7—H8	109.5	C13—C12—C11	120.33 (18)
O1—C1—C6	123.82 (14)	C13—C12—H6A	119.8
O1—C1—C2	114.92 (13)	C11—C12—H6A	119.8
C6—C1—C2	121.25 (14)	C8—C13—C12	119.21 (19)
C3—C2—C1	119.18 (14)	C8—C13—H5A	120.4
C3—C2—H11A	120.4	C12—C13—H5A	120.4
C1—C2—H11A	120.4	O5—C14—O6	123.49 (16)
C2—C3—C4	121.42 (14)	O5—C14—C11	120.18 (15)
C2—C3—O2	117.55 (13)	O6—C14—C11	116.32 (16)
C4—C3—O2	120.84 (13)	O2—C15—C20	123.41 (14)
C5—C4—C3	118.45 (13)	O2—C15—C16	115.32 (14)
C5—C4—H9A	120.8	C20—C15—C16	121.14 (14)
C3—C4—H9A	120.8	C17—C16—C15	119.03 (16)
C4—C5—C6	121.50 (14)	C17—C16—H17A	120.5
C4—C5—C7	120.94 (13)	C15—C16—H17A	120.5
C6—C5—C7	117.54 (14)	C16—C17—C18	120.92 (15)
C1—C6—C5	118.17 (14)	C16—C17—H16A	119.5
C1—C6—H13A	120.9	C18—C17—H16A	119.5
C5—C6—H13A	120.9	C17—C18—C19	119.00 (14)
O4—C7—O3	123.42 (14)	C17—C18—C21	121.08 (14)
O4—C7—C5	122.71 (13)	C19—C18—C21	119.84 (15)
O3—C7—C5	113.86 (13)	C20—C19—C18	120.88 (16)
C13—C8—C9	121.61 (16)	C20—C19—H20A	119.6
C13—C8—O1	118.08 (19)	C18—C19—H20A	119.6
C9—C8—O1	120.15 (18)	C15—C20—C19	119.02 (15)
C8—C9—C10	118.97 (17)	C15—C20—H19A	120.5
C8—C9—H3A	120.5	C19—C20—H19A	120.5
C10—C9—H3A	120.5	O8—C21—O7	122.91 (15)
C11—C10—C9	120.25 (19)	O8—C21—C18	120.30 (14)
C11—C10—H2A	119.9	O7—C21—C18	116.78 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H6···O4i	0.82	1.87	2.6919 (16)	176.4
O6—H3···O8ii	0.82	1.85	2.6615 (18)	169.9
O7—H8···O5iii	0.82	1.82	2.6307 (18)	167.2

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H6⋯O4i	0.82	1.87	2.6919 (16)	176.4
O6—H3⋯O8ii	0.82	1.85	2.6615 (18)	169.9
O7—H8⋯O5iii	0.82	1.82	2.6307 (18)	167.2

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