4,4′-{[1,2-Phenyl­enebis(methyl­ene)]bis­(­oxy)}di­benzoic acid di­methyl­formamide disolvate

Qiu, Z.-Z.; Jing, B.; Li, Q.-X.; Zhu, A.-X.

doi:10.1107/S1600536814006795

organic compounds

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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Pages o534-o535

doi:10.1107/S1600536814006795

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4,4′-{[1,2-Phenylenebis(methylene)]bis(oxy)}dibenzoic acid dimethylformamide disolvate

Zhen-Zhe Qiu,^a Bi Jing,^a Qiu-Xia Li ^a and Ai-Xin Zhu ^a ^*

^aFaculty of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650050, People's Republic of China
^*Correspondence e-mail: zaxchem@126.com

(Received 24 March 2014; accepted 27 March 2014; online 12 April 2014)

In the title solvate, C₂₂H₁₈O₆·2C₃H₇NO, the complete dicarboxylic acid molecule is generated by a crystallographic twofold axis, which bisects the central benzene ring and one N,N-dimethylformamide solvent molecule. The dihedral angle between the central and pendant benzene rings is 54.53 (5)° while that between the pendant rings is 45.44 (5)°. In the crystal, the acid molecules are linked to the solvent molecules via O—H⋯O and weak C—H⋯O hydrogen bonds. Further weak C—H⋯O interactions link adjacent acid molecules into a three-dimensional network.

CCDC reference: 994050

Related literature

For multicarboxylic acid ligands and derivatives used in the synthesis of porous metal-organic frameworks, see: Eddaoudi et al. (2002 ); Eubank et al. (2011 ); Zhang et al. (2012 ). For structures constructed by the acid molecule of the title compound, see: Cao et al. (2009a ); Hu et al. (2013 ). For [Zn(1,2-BAB)(4,4′-bipy)_1/2]_n (H₂BAB =4,4′-{[1,2-phenylenebis(methylene)]bis(oxy)}dibenzoic acid), see Cao et al. (2009a) and for [Cd(1,2-BAB)₂(phen)₂]_n, see: Cao et al. (2009b ). For the synthesis of the title compound, see: Cao et al. (2009a); Rajakumar et al. (2009 ).

Experimental

Crystal data

C₂₂H₁₈O₆·2C₃H₇NO
M_r = 524.56
Monoclinic, C 2/c
a = 12.568 (3) Å
b = 11.081 (2) Å
c = 19.688 (4) Å
β = 98.04 (3)°
V = 2715.0 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.37 × 0.26 × 0.21 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.783, T_max = 1.000
12992 measured reflections
3112 independent reflections
2522 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.132
S = 1.08
3112 reflections
179 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O4	0.90 (2)	1.71 (2)	2.6064 (14)	174 (2)
C3—H3A⋯O1ⁱ	0.93	2.55	3.3714 (17)	147
C8—H8B⋯O2ⁱⁱ	0.97	2.58	3.4920 (18)	157
C14—H14A⋯O2	0.93	2.50	3.2110 (19)	134
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

CCDC reference: 994050

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814006795/bg2524sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814006795/bg2524Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814006795/bg2524Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536814006795/bg2524Isup4.cml

checkCIF report

Comment top

In the past few years, multicarboxylic acids and their derivatives have attracted increasing attention as an important class of ligands used for the synthesis of porous metal organic framework compounds (Eddaoudi et al. 2002; Eubank et al. 2011; Zhang et al. 2012). The acid molecule in the title compound, as a conformationally flexible V-shaped long bicarboxylate ligand, has been already used to synthesize entangled frameworks having both polyrotaxane and polycatenane characteristics that also achieve different topological structures in the entangled system (Cao et al. 2009a; Hu et al. 2013). Although there are crystal structure reports in the literature regarding the title multicarboxylic acid, no crystallographic study has been already performed on the ligand itself.

The crystal structure of the title compound is composed of 4,4'-(1,2-phenylenebis(methylene))bis(oxy)dibenzoic (dicarboxylic) acid and N,N-dimethylformamide and has monoclinic symmetry (space group: C2/c). The acid molecule adopts an E configuration, and contains a crystallographic C2 axis passing through the central benzene group (Fig. 1). The dihedral angles between the benzene rings are 45.44 (5)° and 54.53 (5)°, values which are significantly smaller than those in metal organic frameworks containing the acid molecules with an E configuration (where the acid molecule loses both protons from the carboxylic groups); for example, [Zn(1,2-BAB)(4,4'-bipy)_1/2]_n (4,4'-bipy = 4,4'-Bipyridine) and [Cd(1,2-BAB)₂(phen)₂]_n (phen = 1,10-phenanthroline) the dihedral angles range from 58.2 (1)° to 70.9 (1)° and from 65.6 (1)° to 84.7 (1)°, respectively (Cao et al. 2009a,b).

In the crystal, the acid molecule are linked to the solvent molecules by a strong O—HO and a weak C—HO hydrogen bond [Table 1 (entries 1 and 4) and Fig. 1]. Besides, weak intermolecular C—H···O interactions link the adjacent acid molecules into a three-dimensional network [Table 1 (entries 2 and 3) and Fig 2].

Related literature top

For multicarboxylic acid ligands and derivatives used in the synthesis of porous metal-organic frameworks, see: Eddaoudi et al. (2002); Eubank et al. (2011); Zhang et al. (2012). For structures constructed by the acid molecule of the title compound, see: Cao et al. (2009a); Hu et al. (2013). For [Zn(1,2-BAB)(4,4'-bipy)_1/2]_n, see Cao et al. (2009a) and for [Cd(1,2-BAB)₂(phen)₂]_n, see: Cao et al. (2009b). For the synthesis of the title compound, see: Cao et al. (2009a); Rajakumar et al. (2009).

Experimental top

The ligand 4,4'-(1,2-phenylenebis(methylene))bis(oxy)dibenzoic acid was synthesized according to the literature method (Cao et al. 2009a; Rajakumar et al. 2009). A mixture of 4,4'-(1,2-phenylenebis(methylene))bis(oxy)dibenzoic acid (37.8 mg, 0.1 mmol) and DMF (4 ml) was placed in a Teflon-lined stainless steel vessel (15 ml) and heated at 368 k for 48 h and then cooled to room temperature at a rate of 5 K h-1. The resulting colorless solution slowly evaporated in air for over two weeks and colorless block crystals of the title compound suitable for X-ray diffraction were obtained.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP view of the title compound drawn with 30% probability displacement ellipsoids for the non-H atoms. The intermolecular interactions between the acid and solvent molecules are shown as dashed lines. Symmetry code (A): 1-x, y, -z+1/2.
	Fig. 2. Packing of the acid molecules in the title compound viewed along the b-axis showing the hydrogen bonding interactions with dashed lines. H atoms not involved in H-bonding have been omitted for clarity.

4,4'-{[1,2-Phenylenebis(methylene)]bis(oxy)}dibenzoic acid dimethylformamide disolvate top

Crystal data top

C₂₂H₁₈O₆·2C₃H₇NO	Z = 4
M_r = 524.56	F(000) = 1112
Monoclinic, C2/c	D_x = 1.283 Mg m⁻³
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 12.568 (3) Å	µ = 0.09 mm⁻¹
b = 11.081 (2) Å	T = 293 K
c = 19.688 (4) Å	Block, colorless
β = 98.04 (3)°	0.37 × 0.26 × 0.21 mm
V = 2715.0 (9) Å³

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	3112 independent reflections
Radiation source: fine-focus sealed tube	2522 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −16→16
T_min = 0.783, T_max = 1.000	k = −14→14
12992 measured reflections	l = −25→24

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.132	w = 1/[σ²(F_o²) + (0.0749P)² + 0.5159P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.004
3112 reflections	Δρ_max = 0.20 e Å⁻³
179 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0067 (9)

Crystal data top

C₂₂H₁₈O₆·2C₃H₇NO	V = 2715.0 (9) Å³
M_r = 524.56	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 12.568 (3) Å	µ = 0.09 mm⁻¹
b = 11.081 (2) Å	T = 293 K
c = 19.688 (4) Å	0.37 × 0.26 × 0.21 mm
β = 98.04 (3)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	3112 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2522 reflections with I > 2σ(I)
T_min = 0.783, T_max = 1.000	R_int = 0.023
12992 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.20 e Å⁻³
3112 reflections	Δρ_min = −0.18 e Å⁻³
179 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
O1	0.40156 (8)	0.62429 (9)	0.44602 (5)	0.0603 (3)
H1A	0.3863 (16)	0.701 (2)	0.4567 (11)	0.097 (6)*
O2	0.25800 (8)	0.64860 (9)	0.36718 (5)	0.0634 (3)
O3	0.40553 (7)	0.12257 (8)	0.29461 (5)	0.0542 (3)
O4	0.37129 (9)	0.84725 (9)	0.48090 (5)	0.0697 (3)
N1	0.27647 (9)	1.01724 (11)	0.45297 (6)	0.0612 (3)
C1	0.33217 (9)	0.58739 (11)	0.39294 (6)	0.0454 (3)
C2	0.35606 (9)	0.46508 (10)	0.36834 (6)	0.0426 (3)
C3	0.43792 (10)	0.39435 (11)	0.40211 (6)	0.0466 (3)
H3A	0.4797	0.4243	0.4412	0.056*
C4	0.45868 (10)	0.27970 (11)	0.37878 (6)	0.0477 (3)
H4A	0.5140	0.2333	0.4017	0.057*
C5	0.39532 (9)	0.23540 (10)	0.32053 (6)	0.0442 (3)
C6	0.31335 (10)	0.30568 (12)	0.28570 (7)	0.0523 (3)
H6A	0.2716	0.2758	0.2466	0.063*
C7	0.29425 (10)	0.41968 (12)	0.30942 (6)	0.0497 (3)
H7A	0.2398	0.4667	0.2860	0.060*
C8	0.49311 (10)	0.04951 (11)	0.32584 (6)	0.0477 (3)
H8A	0.4838	0.0308	0.3728	0.057*
H8B	0.5604	0.0927	0.3264	0.057*
C9	0.49515 (9)	−0.06479 (10)	0.28507 (6)	0.0431 (3)
C10	0.49017 (10)	−0.17419 (11)	0.31849 (7)	0.0522 (3)
H10A	0.4834	−0.1747	0.3649	0.063*
C11	0.49509 (11)	−0.28268 (11)	0.28426 (7)	0.0574 (3)
H11A	0.4917	−0.3552	0.3076	0.069*
C12	0.33915 (15)	1.08831 (15)	0.50625 (9)	0.0759 (5)
H12A	0.4015	1.0434	0.5255	0.114*
H12B	0.2962	1.1064	0.5416	0.114*
H12C	0.3613	1.1622	0.4869	0.114*
C13	0.18927 (15)	1.07654 (18)	0.40971 (12)	0.0903 (6)
H13A	0.1600	1.0227	0.3737	0.135*
H13B	0.2158	1.1479	0.3901	0.135*
H13C	0.1342	1.0983	0.4367	0.135*
C14	0.29748 (12)	0.90176 (14)	0.44604 (8)	0.0617 (4)
H14A	0.2537	0.8585	0.4126	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0695 (6)	0.0499 (5)	0.0549 (5)	0.0117 (4)	−0.0139 (4)	−0.0105 (4)
O2	0.0590 (6)	0.0563 (5)	0.0690 (6)	0.0145 (4)	−0.0118 (5)	−0.0082 (4)
O3	0.0496 (5)	0.0479 (5)	0.0597 (5)	0.0077 (4)	−0.0111 (4)	−0.0126 (4)
O4	0.0791 (7)	0.0580 (6)	0.0679 (6)	0.0169 (5)	−0.0038 (5)	−0.0100 (5)
N1	0.0563 (7)	0.0543 (6)	0.0735 (7)	0.0069 (5)	0.0113 (6)	0.0046 (5)
C1	0.0462 (6)	0.0455 (6)	0.0433 (6)	0.0008 (5)	0.0020 (5)	0.0015 (5)
C2	0.0419 (6)	0.0432 (5)	0.0417 (5)	−0.0010 (4)	0.0029 (4)	0.0006 (4)
C3	0.0496 (6)	0.0462 (6)	0.0405 (5)	−0.0010 (5)	−0.0055 (5)	−0.0021 (5)
C4	0.0472 (6)	0.0463 (6)	0.0457 (6)	0.0047 (5)	−0.0069 (5)	0.0002 (5)
C5	0.0422 (6)	0.0433 (6)	0.0456 (6)	−0.0002 (4)	0.0012 (5)	−0.0034 (5)
C6	0.0469 (6)	0.0544 (7)	0.0505 (6)	0.0023 (5)	−0.0108 (5)	−0.0082 (5)
C7	0.0440 (6)	0.0508 (6)	0.0504 (6)	0.0060 (5)	−0.0077 (5)	−0.0013 (5)
C8	0.0475 (6)	0.0476 (6)	0.0457 (6)	0.0048 (5)	−0.0016 (5)	−0.0023 (5)
C9	0.0368 (5)	0.0436 (6)	0.0477 (6)	0.0012 (4)	0.0015 (4)	−0.0005 (4)
C10	0.0530 (7)	0.0503 (6)	0.0535 (6)	0.0002 (5)	0.0078 (5)	0.0066 (5)
C11	0.0549 (7)	0.0422 (6)	0.0753 (8)	−0.0006 (5)	0.0102 (6)	0.0089 (6)
C12	0.0867 (11)	0.0567 (8)	0.0852 (11)	−0.0003 (8)	0.0155 (9)	−0.0087 (8)
C13	0.0650 (10)	0.0815 (11)	0.1215 (16)	0.0154 (9)	0.0034 (10)	0.0215 (11)
C14	0.0602 (8)	0.0604 (8)	0.0635 (8)	0.0056 (6)	0.0056 (6)	−0.0060 (6)

Geometric parameters (Å, º) top

O1—C1	1.3285 (15)	C6—H6A	0.9300
O1—H1A	0.90 (2)	C7—H7A	0.9300
O2—C1	1.2059 (14)	C8—C9	1.5016 (16)
O3—C5	1.3633 (14)	C8—H8A	0.9700
O3—C8	1.4338 (14)	C8—H8B	0.9700
O4—C14	1.2323 (17)	C9—C10	1.3848 (16)
N1—C14	1.3175 (19)	C9—C9ⁱ	1.403 (2)
N1—C13	1.448 (2)	C10—C11	1.3837 (18)
N1—C12	1.453 (2)	C10—H10A	0.9300
C1—C2	1.4841 (16)	C11—C11ⁱ	1.372 (3)
C2—C3	1.3868 (16)	C11—H11A	0.9300
C2—C7	1.3966 (16)	C12—H12A	0.9600
C3—C4	1.3879 (17)	C12—H12B	0.9600
C3—H3A	0.9300	C12—H12C	0.9600
C4—C5	1.3911 (16)	C13—H13A	0.9600
C4—H4A	0.9300	C13—H13B	0.9600
C5—C6	1.3929 (16)	C13—H13C	0.9600
C6—C7	1.3794 (18)	C14—H14A	0.9300

C1—O1—H1A	109.6 (13)	C9—C8—H8A	110.0
C5—O3—C8	117.65 (9)	O3—C8—H8B	110.0
C14—N1—C13	121.73 (14)	C9—C8—H8B	110.0
C14—N1—C12	120.34 (13)	H8A—C8—H8B	108.4
C13—N1—C12	117.91 (14)	C10—C9—C9ⁱ	118.91 (7)
O2—C1—O1	122.79 (11)	C10—C9—C8	118.63 (11)
O2—C1—C2	123.80 (11)	C9ⁱ—C9—C8	122.44 (7)
O1—C1—C2	113.41 (10)	C11—C10—C9	121.41 (12)
C3—C2—C7	118.94 (11)	C11—C10—H10A	119.3
C3—C2—C1	122.01 (10)	C9—C10—H10A	119.3
C7—C2—C1	119.05 (10)	C11ⁱ—C11—C10	119.68 (8)
C4—C3—C2	121.32 (10)	C11ⁱ—C11—H11A	120.2
C4—C3—H3A	119.3	C10—C11—H11A	120.2
C2—C3—H3A	119.3	N1—C12—H12A	109.5
C3—C4—C5	118.90 (10)	N1—C12—H12B	109.5
C3—C4—H4A	120.5	H12A—C12—H12B	109.5
C5—C4—H4A	120.5	N1—C12—H12C	109.5
O3—C5—C4	124.01 (10)	H12A—C12—H12C	109.5
O3—C5—C6	115.48 (10)	H12B—C12—H12C	109.5
C4—C5—C6	120.49 (11)	N1—C13—H13A	109.5
C7—C6—C5	119.81 (10)	N1—C13—H13B	109.5
C7—C6—H6A	120.1	H13A—C13—H13B	109.5
C5—C6—H6A	120.1	N1—C13—H13C	109.5
C6—C7—C2	120.54 (10)	H13A—C13—H13C	109.5
C6—C7—H7A	119.7	H13B—C13—H13C	109.5
C2—C7—H7A	119.7	O4—C14—N1	124.37 (14)
O3—C8—C9	108.45 (9)	O4—C14—H14A	117.8
O3—C8—H8A	110.0	N1—C14—H14A	117.8

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O4	0.90 (2)	1.71 (2)	2.6064 (14)	174 (2)
C3—H3A···O1ⁱⁱ	0.93	2.55	3.3714 (17)	147
C8—H8B···O2ⁱⁱⁱ	0.97	2.58	3.4920 (18)	157
C14—H14A···O2	0.93	2.50	3.2110 (19)	134

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O4	0.90 (2)	1.71 (2)	2.6064 (14)	174 (2)
C3—H3A···O1ⁱ	0.93	2.55	3.3714 (17)	146.9
C8—H8B···O2ⁱⁱ	0.97	2.58	3.4920 (18)	157.3
C14—H14A···O2	0.93	2.50	3.2110 (19)	133.9

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

Acknowledgements

The authors thank the Science and Technology Department (2010ZC070, 2011FZ080 and 2012FB141) of Yunnan Province for supporting this work.

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Cao, X.-Y., Yao, Y.-G., Batten, S. R., Ma, E., Qin, Y.-Y., Zhang, J., Zhang, R.-B. & Cheng, J.-K. (2009a). CrystEngComm, 11, 1030–1036. Web of Science CSD CrossRef CAS Google Scholar
Cao, X.-Y., Yao, Y.-G., Qin, Y.-Y., Lin, Q.-P., Li, Z.-J., Cheng, J.-K. & Zhang, R.-B. (2009b). CrystEngComm, 11, 1815–1818. Web of Science CSD CrossRef Google Scholar
Eddaoudi, M., Kim, J., Rosi, N., Vodak, D., Wachter, J., O'Keeffe, M. & Yaghi, O. M. (2002). Science, 295, 469–472. Web of Science CSD CrossRef PubMed CAS Google Scholar
Eubank, J. F., Mouttaki, H., Cairns, A. J., Belmabkhout, Y., Wojtas, L., Luebke, R., Alkordi, M. & Eddaoudi, M. (2011). J. Am. Chem. Soc. 133, 14204–14207. Web of Science CSD CrossRef CAS PubMed Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Hu, F.-L., Wu, W., Liang, P., Gu, Y.-Q., Zhu, L.-G., Wei, H. & Lang, J.-P. (2013). Cryst. Growth Des. 13, 5050–5061. Web of Science CSD CrossRef CAS Google Scholar
Rajakumar, P., Sekar, K., Shanmugaiah, V. & Mathivanan, N. (2009). Eur. J. Med. Chem. 44, 3040–3045. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, Y.-B., Zhou, H.-L., Lin, R.-B., Zhang, C., Lin, J.-B., Zhang, J.-P. & Chen, X.-M. (2012). Nat. Commun. 3, 642. Web of Science CSD CrossRef PubMed Google Scholar

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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Pages o534-o535

doi:10.1107/S1600536814006795

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4,4′-{[1,2-Phenyl­enebis(methyl­ene)]bis­­(­­oxy)}di­benzoic acid di­methyl­formamide disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4,4′-{[1,2-Phenylenebis(methylene)]bis(oxy)}dibenzoic acid dimethylformamide disolvate