1,3-Di-4-pyridylpropane-4,4'-oxy-dibenzoic acid (1/1).

The hydro-thermal reaction of Cd(NO(3))(2)·4H(2)O, 1,3-di-4-pyridylpropane (BPP) and 4,4'-oxydibenzoic acid (OBA) led to the formation of the title compound, C(13)H(14)N(2)·C(14)H(10)O(5). The asymmetric unit consists of one mol-ecule of OBA and one of BPP. In the OBA mol-ecule, one COOH group is nearly planar with its attached benzene ring [dihedral angle = 0.9 (1)°], while the other COOH group is slightly twisted with a dihedral angle of 10.8 (3)°. The carboxyl groups form strong inter-molecular O-H⋯N hydrogen bonds with N atoms of the pyridine rings in BPP, linking the mol-ecules into zigzag chains.

Related literature

For general background see: Belcher et al. (2002 ▶); Hagrman et al. (1999 ▶); Han et al. (2007 ▶); Luan et al. (2005 ▶); Nguyen et al. (2006 ▶); Wang et al. (2005 ▶); Yaghi et al. (1998 ▶). For related structures, see: Dai et al. (2005 ▶); Ma et al. (2006 ▶); Hou et al. (2008 ▶); Lee et al. (2003 ▶); Wang et al. (2008 ▶); Najafpour et al. (2008 ▶). For an idependent determination of this structure, see: Dong et al. (2008 ▶).

Experimental

Crystal data

C13H14N2·C14H10O5

M = 456.48

Triclinic,

a = 6.8938 (3) Å

b = 11.5869 (6) Å

c = 14.9570 (9) Å

α = 86.493 (4)°

β = 81.157 (4)°

γ = 74.016 (3)°

V = 1134.67 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 (2) K

0.47 × 0.45 × 0.45 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.957, T max = 0.962

8404 measured reflections

5645 independent reflections

2932 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.147

S = 1.01

5645 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXS97; software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803331X/fl2221sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803331X/fl2221Isup2.hkl

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

C13H14N2·C14H10O5	Z = 2
Mr = 456.48	F000 = 480
Triclinic, P1	Dx = 1.336 Mg m−3
Hall symbol: -P1	Melting point: not measured K
a = 6.8938 (3) Å	Mo Kα radiation λ = 0.71073 Å
b = 11.5869 (6) Å	Cell parameters from 5645 reflections
c = 14.9570 (9) Å	θ = 1.8–28.4º
α = 86.493 (4)º	µ = 0.09 mm−1
β = 81.157 (4)º	T = 298 (2) K
γ = 74.016 (3)º	Block, colourless
V = 1134.67 (10) Å3	0.47 × 0.45 × 0.45 mm

Bruker SMART CCD area-detector diffractometer	5645 independent reflections
Radiation source: fine-focus sealed tube	2932 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.022
Detector resolution: 9.00cm pixels mm-1	θmax = 28.4º
T = 298(2) K	θmin = 1.8º
φ and ω scans	h = −8→9
Absorption correction: multi-scan(SADABS; Bruker, 2002)	k = −14→15
Tmin = 0.957, Tmax = 0.962	l = −19→16
8404 measured reflections

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)] = 0.052	H-atom parameters constrained
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.0616P)2 + 0.0668P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
5645 reflections	Δρmax = 0.19 e Å−3
307 parameters	Δρmin = −0.27 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
N1	−0.1086 (2)	0.38623 (14)	0.57527 (11)	0.0497 (4)
N2	0.6799 (2)	0.69499 (14)	0.97352 (11)	0.0497 (4)
C15	0.0705 (3)	0.38146 (18)	0.59963 (16)	0.0580 (6)
H15	0.1800	0.3156	0.5827	0.080*
C16	0.1014 (3)	0.46960 (19)	0.64881 (16)	0.0571 (6)
H16	0.2301	0.4623	0.6640	0.080*
C17	−0.0570 (3)	0.56910 (16)	0.67593 (13)	0.0427 (5)
C18	−0.2430 (3)	0.57321 (17)	0.64994 (14)	0.0488 (5)
H18	−0.3553	0.6379	0.6662	0.080*
C19	−0.2627 (3)	0.48237 (19)	0.60034 (15)	0.0527 (5)
H19	−0.3893	0.4879	0.5834	0.080*
C20	−0.0312 (3)	0.67052 (17)	0.72756 (14)	0.0508 (5)
H20A	−0.1531	0.6990	0.7709	0.080*
H20B	−0.0205	0.7362	0.6854	0.080*
C21	0.1517 (3)	0.63922 (18)	0.77781 (15)	0.0541 (5)
H21A	0.1416	0.5743	0.8209	0.080*
H21B	0.2747	0.6112	0.7350	0.080*
C22	0.1678 (3)	0.74500 (17)	0.82751 (15)	0.0538 (5)
H22A	0.0454	0.7708	0.8710	0.080*
H22B	0.1703	0.8106	0.7842	0.080*
C23	0.6401 (3)	0.60151 (18)	0.93963 (15)	0.0564 (6)
H23	0.7250	0.5252	0.9483	0.080*
C24	0.4788 (3)	0.61262 (17)	0.89228 (15)	0.0539 (6)
H24	0.4566	0.5445	0.8705	0.080*
C25	0.3504 (3)	0.72434 (17)	0.87710 (13)	0.0437 (5)
C26	0.3944 (3)	0.82112 (17)	0.91119 (15)	0.0504 (5)
H26	0.3140	0.8986	0.9022	0.080*
C27	0.5568 (3)	0.80294 (18)	0.95832 (15)	0.0528 (5)
H27	0.5821	0.8696	0.9808	0.080*
O1	0.6084 (2)	−0.16655 (12)	0.27513 (10)	0.0580 (4)
O2	0.5302 (2)	0.29158 (14)	0.50942 (13)	0.0798 (6)
O3	0.8616 (2)	0.20798 (13)	0.48596 (12)	0.0716 (5)
H3	0.8631	0.2642	0.5163	0.080*
O4	−0.1236 (2)	−0.11337 (12)	0.04949 (11)	0.0666 (5)
O5	−0.0307 (2)	−0.31076 (12)	0.07640 (11)	0.0603 (4)
H5	−0.1219	−0.3094	0.0467	0.080*
C1	0.6118 (3)	−0.06807 (16)	0.32224 (13)	0.0440 (5)
C2	0.4410 (3)	0.01727 (18)	0.35955 (14)	0.0496 (5)
H2	0.3120	0.0137	0.3510	0.080*
C3	0.4625 (3)	0.10781 (17)	0.40961 (14)	0.0477 (5)
H3A	0.3471	0.1655	0.4346	0.080*
C4	0.6537 (3)	0.11418 (16)	0.42333 (13)	0.0412 (4)
C5	0.8235 (3)	0.02569 (18)	0.38713 (14)	0.0487 (5)
H5A	0.9524	0.0275	0.3972	0.080*
C6	0.8041 (3)	−0.06484 (17)	0.33646 (14)	0.0500 (5)
H6	0.9190	−0.1232	0.3120	0.080*
C7	0.6739 (3)	0.21355 (17)	0.47726 (14)	0.0481 (5)
C8	0.4451 (3)	−0.16717 (17)	0.23154 (13)	0.0454 (5)
C9	0.3450 (3)	−0.07097 (17)	0.18192 (14)	0.0519 (5)
H9	0.3782	0.0018	0.1802	0.080*
C10	0.1958 (3)	−0.08367 (16)	0.13509 (14)	0.0486 (5)
H10	0.1277	−0.0188	0.1019	0.080*
C11	0.1450 (3)	−0.19174 (16)	0.13651 (13)	0.0408 (4)
C12	0.2458 (3)	−0.28742 (16)	0.18693 (14)	0.0481 (5)
H12	0.2126	−0.3602	0.1889	0.080*
C13	0.3958 (3)	−0.27513 (17)	0.23433 (15)	0.0513 (5)
H13	0.4635	−0.3396	0.2681	0.080*
C14	−0.0170 (3)	−0.20004 (17)	0.08383 (13)	0.0442 (5)

	U11	U22	U33	U12	U13	U23
N1	0.0480 (10)	0.0533 (10)	0.0517 (11)	−0.0151 (8)	−0.0135 (8)	−0.0097 (8)
N2	0.0498 (10)	0.0505 (10)	0.0547 (11)	−0.0163 (8)	−0.0186 (8)	−0.0058 (8)
C15	0.0486 (12)	0.0560 (13)	0.0700 (16)	−0.0095 (10)	−0.0119 (11)	−0.0195 (11)
C16	0.0407 (11)	0.0625 (13)	0.0725 (15)	−0.0109 (10)	−0.0191 (10)	−0.0214 (11)
C17	0.0419 (10)	0.0467 (11)	0.0425 (11)	−0.0126 (9)	−0.0128 (9)	−0.0054 (8)
C18	0.0422 (11)	0.0497 (11)	0.0563 (13)	−0.0094 (9)	−0.0166 (10)	−0.0059 (9)
C19	0.0462 (11)	0.0579 (13)	0.0600 (14)	−0.0157 (10)	−0.0210 (10)	−0.0052 (10)
C20	0.0483 (11)	0.0509 (12)	0.0578 (13)	−0.0129 (9)	−0.0184 (10)	−0.0124 (10)
C21	0.0516 (12)	0.0544 (12)	0.0625 (14)	−0.0151 (10)	−0.0207 (10)	−0.0132 (10)
C22	0.0558 (12)	0.0519 (12)	0.0594 (14)	−0.0136 (10)	−0.0236 (10)	−0.0101 (10)
C23	0.0604 (13)	0.0476 (12)	0.0682 (15)	−0.0155 (10)	−0.0284 (11)	−0.0020 (10)
C24	0.0617 (13)	0.0434 (11)	0.0655 (15)	−0.0189 (10)	−0.0251 (11)	−0.0083 (10)
C25	0.0470 (11)	0.0456 (11)	0.0423 (11)	−0.0156 (9)	−0.0111 (9)	−0.0052 (8)
C26	0.0489 (11)	0.0431 (11)	0.0625 (14)	−0.0116 (9)	−0.0165 (10)	−0.0099 (9)
C27	0.0516 (12)	0.0496 (12)	0.0635 (14)	−0.0171 (10)	−0.0155 (10)	−0.0157 (10)
O1	0.0535 (8)	0.0512 (8)	0.0755 (11)	−0.0093 (6)	−0.0305 (7)	−0.0179 (7)
O2	0.0523 (9)	0.0721 (11)	0.1135 (15)	0.0026 (8)	−0.0246 (9)	−0.0481 (10)
O3	0.0488 (9)	0.0740 (10)	0.0991 (13)	−0.0148 (7)	−0.0181 (8)	−0.0448 (9)
O4	0.0742 (10)	0.0471 (8)	0.0893 (12)	−0.0147 (7)	−0.0498 (9)	0.0038 (8)
O5	0.0661 (9)	0.0437 (8)	0.0821 (11)	−0.0164 (7)	−0.0396 (8)	−0.0061 (7)
C1	0.0472 (11)	0.0451 (11)	0.0449 (12)	−0.0148 (9)	−0.0160 (9)	−0.0064 (8)
C2	0.0375 (10)	0.0591 (12)	0.0571 (13)	−0.0141 (9)	−0.0171 (9)	−0.0078 (10)
C3	0.0368 (10)	0.0536 (12)	0.0527 (13)	−0.0070 (9)	−0.0124 (9)	−0.0098 (9)
C4	0.0405 (10)	0.0450 (10)	0.0398 (11)	−0.0110 (8)	−0.0104 (8)	−0.0057 (8)
C5	0.0359 (10)	0.0578 (12)	0.0559 (13)	−0.0147 (9)	−0.0084 (9)	−0.0147 (10)
C6	0.0392 (10)	0.0552 (12)	0.0563 (13)	−0.0104 (9)	−0.0074 (9)	−0.0156 (10)
C7	0.0460 (11)	0.0496 (12)	0.0513 (13)	−0.0100 (10)	−0.0171 (10)	−0.0086 (9)
C8	0.0463 (11)	0.0472 (11)	0.0471 (12)	−0.0127 (9)	−0.0166 (9)	−0.0089 (9)
C9	0.0659 (13)	0.0433 (11)	0.0557 (13)	−0.0234 (10)	−0.0220 (11)	0.0014 (9)
C10	0.0596 (12)	0.0423 (11)	0.0493 (12)	−0.0155 (9)	−0.0212 (10)	0.0001 (9)
C11	0.0438 (10)	0.0393 (10)	0.0418 (11)	−0.0115 (8)	−0.0109 (9)	−0.0059 (8)
C12	0.0533 (11)	0.0383 (10)	0.0581 (13)	−0.0142 (9)	−0.0199 (10)	−0.0021 (9)
C13	0.0551 (12)	0.0412 (11)	0.0613 (14)	−0.0104 (9)	−0.0256 (10)	0.0009 (9)
C14	0.0453 (11)	0.0411 (11)	0.0484 (12)	−0.0112 (9)	−0.0118 (9)	−0.0071 (9)

N1—C15	1.326 (2)	O1—C1	1.385 (2)
N1—C19	1.337 (2)	O1—C8	1.387 (2)
N2—C27	1.333 (2)	O2—C7	1.202 (2)
N2—C23	1.334 (2)	O3—C7	1.304 (2)
C15—C16	1.375 (3)	O3—H3	0.8200
C15—H15	0.9300	O4—C14	1.208 (2)
C16—C17	1.383 (3)	O5—C14	1.325 (2)
C16—H16	0.9300	O5—H5	0.8200
C17—C18	1.384 (2)	C1—C2	1.379 (3)
C17—C20	1.509 (2)	C1—C6	1.385 (2)
C18—C19	1.372 (3)	C2—C3	1.378 (3)
C18—H18	0.9300	C2—H2	0.9300
C19—H19	0.9300	C3—C4	1.387 (2)
C20—C21	1.514 (3)	C3—H3A	0.9300
C20—H20A	0.9700	C4—C5	1.388 (2)
C20—H20B	0.9700	C4—C7	1.494 (2)
C21—C22	1.510 (3)	C5—C6	1.378 (2)
C21—H21A	0.9700	C5—H5A	0.9300
C21—H21B	0.9700	C6—H6	0.9300
C22—C25	1.514 (3)	C8—C9	1.379 (3)
C22—H22A	0.9700	C8—C13	1.380 (3)
C22—H22B	0.9700	C9—C10	1.374 (3)
C23—C24	1.381 (3)	C9—H9	0.9300
C23—H23	0.9300	C10—C11	1.388 (2)
C24—C25	1.380 (3)	C10—H10	0.9300
C24—H24	0.9300	C11—C12	1.384 (3)
C25—C26	1.384 (2)	C11—C14	1.489 (2)
C26—C27	1.374 (3)	C12—C13	1.382 (3)
C26—H26	0.9300	C12—H12	0.9300
C27—H27	0.9300	C13—H13	0.9300
C15—N1—C19	117.07 (16)	N2—C27—H27	118.2
C27—N2—C23	116.59 (16)	C26—C27—H27	118.2
N1—C15—C16	122.91 (18)	C1—O1—C8	122.02 (14)
N1—C15—H15	118.5	C7—O3—H3	109.5
C16—C15—H15	118.5	C14—O5—H5	109.5
C15—C16—C17	120.72 (17)	C2—C1—C6	120.44 (16)
C15—C16—H16	119.6	C2—C1—O1	124.67 (16)
C17—C16—H16	119.6	C6—C1—O1	114.70 (16)
C16—C17—C18	115.85 (17)	C3—C2—C1	119.62 (17)
C16—C17—C20	123.19 (16)	C3—C2—H2	120.2
C18—C17—C20	120.92 (16)	C1—C2—H2	120.2
C19—C18—C17	120.35 (17)	C2—C3—C4	120.95 (17)
C19—C18—H18	119.8	C2—C3—H3A	119.5
C17—C18—H18	119.8	C4—C3—H3A	119.5
N1—C19—C18	123.10 (17)	C3—C4—C5	118.54 (16)
N1—C19—H19	118.4	C3—C4—C7	120.15 (16)
C18—C19—H19	118.4	C5—C4—C7	121.30 (16)
C17—C20—C21	115.27 (16)	C6—C5—C4	121.02 (16)
C17—C20—H20A	108.5	C6—C5—H5A	119.5
C21—C20—H20A	108.5	C4—C5—H5A	119.5
C17—C20—H20B	108.5	C5—C6—C1	119.39 (17)
C21—C20—H20B	108.5	C5—C6—H6	120.3
H20A—C20—H20B	107.5	C1—C6—H6	120.3
C22—C21—C20	112.25 (16)	O2—C7—O3	123.16 (17)
C22—C21—H21A	109.2	O2—C7—C4	122.99 (17)
C20—C21—H21A	109.2	O3—C7—C4	113.85 (16)
C22—C21—H21B	109.2	C9—C8—C13	120.40 (17)
C20—C21—H21B	109.2	C9—C8—O1	123.73 (17)
H21A—C21—H21B	107.9	C13—C8—O1	115.68 (17)
C21—C22—C25	116.41 (17)	C10—C9—C8	119.34 (17)
C21—C22—H22A	108.2	C10—C9—H9	120.3
C25—C22—H22A	108.2	C8—C9—H9	120.3
C21—C22—H22B	108.2	C9—C10—C11	121.15 (18)
C25—C22—H22B	108.2	C9—C10—H10	119.4
H22A—C22—H22B	107.3	C11—C10—H10	119.4
N2—C23—C24	123.12 (18)	C12—C11—C10	118.96 (17)
N2—C23—H23	118.4	C12—C11—C14	122.47 (17)
C24—C23—H23	118.4	C10—C11—C14	118.57 (17)
C25—C24—C23	120.29 (17)	C13—C12—C11	120.16 (17)
C25—C24—H24	119.9	C13—C12—H12	119.9
C23—C24—H24	119.9	C11—C12—H12	119.9
C24—C25—C26	116.32 (17)	C8—C13—C12	119.99 (18)
C24—C25—C22	124.00 (16)	C8—C13—H13	120.0
C26—C25—C22	119.67 (17)	C12—C13—H13	120.0
C27—C26—C25	120.08 (18)	O4—C14—O5	123.14 (17)
C27—C26—H26	120.0	O4—C14—C11	122.70 (17)
C25—C26—H26	120.0	O5—C14—C11	114.15 (16)
N2—C27—C26	123.58 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1i	0.82	1.78	2.598 (2)	174.0
O5—H5···N2ii	0.82	1.87	2.685 (2)	176.9

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N1i	0.82	1.78	2.598 (2)	174
O5—H5⋯N2ii	0.82	1.87	2.685 (2)	177

Symmetry codes: (i) ; (ii) .