4,4'-{[1,2-Phenyl-enebis(methyl-ene)]bis-(-oxy)}di-benzoic acid di-methyl-formamide disolvate.

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-di-methyl-formamide solvent mol-ecule. 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 inter-actions link adjacent acid mol-ecules into a three-dimensional network.

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] (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], 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 = 524.56

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.132

S = 1.08

3112 reflections

179 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814006795/bg2524sup1.cif

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

Click here for additional data file.

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

Click here for additional data file.

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

CCDC reference: 994050

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H18O6·2C3H7NO	Z = 4
Mr = 524.56	F(000) = 1112
Monoclinic, C2/c	Dx = 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

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

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(Fo2) + (0.0749P)2 + 0.5159P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.004
3112 reflections	Δρmax = 0.20 e Å−3
179 parameters	Δρmin = −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)

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	0.40156 (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*

	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)

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

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

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) ; (ii) .