4,4'-(Propane-1,3-di-yl)dibenzoic acid.

The complete molecule of the title compound, C(17)H(16)O(4), is generated by crystallographic twofold symmetry, with the central C atom lying on the rotation axis and a dihedral angle between the benzene rings of 81.9 (2)°. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonding between carboxyl groups, forming one-dimensional supra-molecular chains.

Related literature

For general background, see: Bradshaw et al. (2005 ▶); Eddaoudi et al. (2001 ▶); Heo et al. (2007 ▶); Kesanli & Lin (2003 ▶). For related structures, see: Dai et al. (2005 ▶); Li et al. (2007 ▶); Ma et al. (2006 ▶). For the synthesis, see: Cram & Steinberg (1951 ▶).

Experimental

Crystal data

C17H16O4

M = 284.30

Monoclinic,

a = 14.569 (3) Å

b = 4.7337 (6) Å

c = 21.463 (3) Å

β = 102.722 (10)°

V = 1443.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.48 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.947, T max = 0.989

3830 measured reflections

1276 independent reflections

688 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.115

S = 0.94

1276 reflections

96 parameters

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.17 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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033005/xu2559sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033005/xu2559Isup2.hkl

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

C17H16O4	F(000) = 600
Mr = 284.30	Dx = 1.308 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 750 reflections
a = 14.569 (3) Å	θ = 2.9–24.2°
b = 4.7337 (6) Å	µ = 0.09 mm−1
c = 21.463 (3) Å	T = 298 K
β = 102.722 (10)°	Block, colourless
V = 1443.8 (4) Å3	0.48 × 0.20 × 0.16 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1276 independent reflections
Radiation source: fine-focus sealed tube	688 reflections with I > 2σ(I)
graphite	Rint = 0.059
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −11→17
Tmin = 0.947, Tmax = 0.989	k = −5→5
3830 measured reflections	l = −25→25

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 0.94	w = 1/[σ2(Fo2) + (0.0552P)2] where P = (Fo2 + 2Fc2)/3
1276 reflections	(Δ/σ)max < 0.001
96 parameters	Δρmax = 0.11 e Å−3
0 restraints	Δρmin = −0.17 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	Occ. (<1)
O1	0.78668 (11)	−0.0453 (3)	0.56693 (7)	0.0686 (5)
O2	0.64734 (11)	−0.0622 (4)	0.49904 (8)	0.0698 (5)
H2	0.6756	−0.1758	0.4813	0.080*
C1	0.5000	0.6425 (6)	0.7500	0.0519 (9)
H1A	0.5479	0.5215	0.7752	0.080*	0.50
H1B	0.4521	0.5215	0.7248	0.080*	0.50
C2	0.54479 (15)	0.8179 (4)	0.70454 (9)	0.0514 (6)
H2A	0.4973	0.9372	0.6784	0.080*
H2B	0.5931	0.9392	0.7291	0.080*
C3	0.58765 (16)	0.6279 (4)	0.66203 (10)	0.0443 (6)
C4	0.53260 (16)	0.5110 (5)	0.60728 (11)	0.0543 (6)
H4	0.4695	0.5617	0.5951	0.080*
C5	0.56894 (16)	0.3211 (5)	0.57026 (10)	0.0522 (6)
H5	0.5303	0.2454	0.5338	0.080*
C6	0.66296 (15)	0.2426 (4)	0.58731 (10)	0.0426 (5)
C7	0.71907 (16)	0.3612 (5)	0.64125 (11)	0.0543 (6)
H7	0.7824	0.3129	0.6530	0.080*
C8	0.68157 (17)	0.5525 (5)	0.67812 (10)	0.0552 (6)
H8	0.7203	0.6309	0.7142	0.080*
C9	0.70274 (16)	0.0329 (4)	0.54925 (10)	0.0465 (6)

	U11	U22	U33	U12	U13	U23
O1	0.0486 (10)	0.0791 (12)	0.0795 (12)	0.0089 (9)	0.0173 (9)	−0.0169 (10)
O2	0.0677 (11)	0.0776 (12)	0.0656 (11)	0.0136 (10)	0.0178 (10)	−0.0211 (10)
C1	0.067 (2)	0.0450 (18)	0.0520 (19)	0.000	0.0308 (18)	0.000
C2	0.0647 (15)	0.0428 (12)	0.0544 (14)	0.0017 (11)	0.0301 (13)	0.0015 (11)
C3	0.0562 (14)	0.0385 (12)	0.0441 (13)	0.0000 (11)	0.0239 (12)	0.0053 (11)
C4	0.0504 (14)	0.0615 (15)	0.0524 (14)	0.0090 (12)	0.0144 (13)	−0.0025 (12)
C5	0.0536 (14)	0.0584 (15)	0.0448 (13)	0.0060 (12)	0.0113 (12)	−0.0049 (11)
C6	0.0476 (13)	0.0419 (12)	0.0419 (13)	0.0000 (11)	0.0178 (11)	0.0033 (10)
C7	0.0469 (13)	0.0603 (15)	0.0574 (14)	0.0035 (12)	0.0148 (12)	−0.0039 (13)
C8	0.0561 (15)	0.0594 (14)	0.0505 (14)	0.0008 (13)	0.0125 (13)	−0.0079 (12)
C9	0.0511 (15)	0.0471 (14)	0.0438 (14)	−0.0032 (12)	0.0158 (13)	0.0003 (11)

O1—C9	1.254 (2)	C3—C4	1.384 (3)
O2—C9	1.278 (2)	C4—C5	1.380 (3)
O2—H2	0.8200	C4—H4	0.9300
C1—C2	1.532 (2)	C5—C6	1.388 (3)
C1—C2i	1.532 (2)	C5—H5	0.9300
C1—H1A	0.9700	C6—C7	1.381 (3)
C1—H1B	0.9700	C6—C9	1.482 (3)
C2—C3	1.511 (3)	C7—C8	1.391 (3)
C2—H2A	0.9700	C7—H7	0.9300
C2—H2B	0.9700	C8—H8	0.9300
C3—C8	1.382 (3)
C9—O2—H2	109.5	C5—C4—H4	119.2
C2—C1—C2i	114.4 (2)	C3—C4—H4	119.2
C2—C1—H1A	108.7	C4—C5—C6	120.3 (2)
C2i—C1—H1A	108.7	C4—C5—H5	119.9
C2—C1—H1B	108.7	C6—C5—H5	119.9
C2i—C1—H1B	108.7	C7—C6—C5	118.7 (2)
H1A—C1—H1B	107.6	C7—C6—C9	120.2 (2)
C3—C2—C1	110.64 (17)	C5—C6—C9	121.1 (2)
C3—C2—H2A	109.5	C6—C7—C8	120.5 (2)
C1—C2—H2A	109.5	C6—C7—H7	119.8
C3—C2—H2B	109.5	C8—C7—H7	119.8
C1—C2—H2B	109.5	C3—C8—C7	121.1 (2)
H2A—C2—H2B	108.1	C3—C8—H8	119.4
C8—C3—C4	117.7 (2)	C7—C8—H8	119.4
C8—C3—C2	121.4 (2)	O1—C9—O2	122.9 (2)
C4—C3—C2	120.8 (2)	O1—C9—C6	120.3 (2)
C5—C4—C3	121.7 (2)	O2—C9—C6	116.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ii	0.82	1.84	2.642 (2)	167.6

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	1.84	2.642 (2)	168

Symmetry code: (i) .