4,4′-(Propane-1,3-di­yl)dibenzoic acid

Hua, J.; Gao, L.

doi:10.1107/S1600536809033005

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2233

doi:10.1107/S1600536809033005

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4,4′-(Propane-1,3-diyl)dibenzoic acid

Jia Hua ^a ^* and Lu Gao ^a

^aState Key Laboratory of Inorganic Synthesis and Preparative Chemistry, College of Chemistry, Jilin University, Changchun 130012, People's Republic of China
^*Correspondence e-mail: huajia@jlu.edu.cn

(Received 17 July 2009; accepted 19 August 2009; online 26 August 2009)

The complete molecule of the title compound, C₁₇H₁₆O₄, 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, molecules are linked by O—H⋯O hydrogen bonding between carboxyl groups, forming one-dimensional supramolecular 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_r = 284.30
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.115
S = 0.94
1276 reflections
96 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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) $[-x+{\script{3\over 2}}, -y-{\script{1\over 2}}, -z+1]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

In the past decades the design and synthesis of metal-organic frameworks have received extensive attention in the field of supra-molecular chemistry and crystal engineering (Bradshaw et al., 2005; Eddaoudi et al., 2001; Heo et al., 2007; Kesanli et al., 2003). As part of our investigation on the metal-organic frameworks (Dai et al., 2005; Li et al., 2007; Ma et al., 2006), we report here the crystal structure of the title compound.

In the crystal structure, the title molecule has site symmetry 2, the C1 atom is located on a twofold rotation axis. The two symmetry-related benzene rings are twisted with respect to each other with a dihedral angle of 81.9 (2)° (Fig. 1). The carboxylic acid groups of neighboring molecules form strong intermolecular O—H···O hydrogen bonds (Table 1), linking the molecules into the one-dimensional supra-molecular chains (Fig. 2).

Related literature top

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 top

4,4'-(Propane-1,3-diyl)dibenzoic acid was synthesized according to literature methods (Cram & Steinberg, 1951), and other reagents were commercially obtained without further purification. In a typical synthesis procedure for the title compound, the reactants Zn(NO₃)₂.6H₂O (0.149 g, 0.5 mmol), 4,4'-(propane-1,3-diyl)dibenzoic acid (0.142 g, 0.5 mmol), HCl (38%, 0.30 ml) and triethylamine (0.35 ml) were mixed in water (5 ml). The mixture was placed in a 15 ml Teflon-lined stainless steel autoclave with a filling capacity of 37.7% and heated under autogenous pressure for 5 d at 453 K. After slow cooling to room temperature, the block-shaped colourless crystals suitable for X-ray diffraction were obtained.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); 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).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids at 50% probability level [symmetry code: (i) 1 - x, y, -z + 3/2].
	Fig. 2. A diagram showing the one-dimensional supra-molecular chain formed by intermolecular O—H···O hydrogen bonding (dashed lines).

4,4'-(Propane-1,3-diyl)dibenzoic acid top

Crystal data top

C₁₇H₁₆O₄	F(000) = 600
M_r = 284.30	D_x = 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

Data collection top

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

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0552P)²] where P = (F_o² + 2F_c²)/3
1276 reflections	(Δ/σ)_max < 0.001
96 parameters	Δρ_max = 0.11 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₇H₁₆O₄	V = 1443.8 (4) Å³
M_r = 284.30	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 14.569 (3) Å	µ = 0.09 mm⁻¹
b = 4.7337 (6) Å	T = 298 K
c = 21.463 (3) Å	0.48 × 0.20 × 0.16 mm
β = 102.722 (10)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1276 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	688 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.989	R_int = 0.059
3830 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 0.94	Δρ_max = 0.11 e Å⁻³
1276 reflections	Δρ_min = −0.17 e Å⁻³
96 parameters

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	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (ii) −x+3/2, −y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆O₄
M_r	284.30
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	14.569 (3), 4.7337 (6), 21.463 (3)
β (°)	102.722 (10)
V (Å³)	1443.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.48 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.947, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	3830, 1276, 688
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.115, 0.94
No. of reflections	1276
No. of parameters	96
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.17

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.84	2.642 (2)	167.6

Symmetry code: (i) −x+3/2, −y−1/2, −z+1.

Acknowledgements

We thank the National Natural Science Foundation of China.

References

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