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

In the title compound, C(13)H(14)N(2)·C(14)H(10)O(5), a 1:1 cocrystal of 1,3-di-4-pyridylpropane (bpp) and 4,4'-oxydibenzoic acid (H(2)oba), the dihedral angle between the two benzene rings of the flexible H(2)oba mol-ecule is 57.07 (1)°; the two pyridine rings of bpp make a dihedral angle of 27.52 (1)°. Strong inter-molecular O-H⋯N hydrogen bonds link the mol-ecules into chains, which are then linked into a three-dimensional network through inter-molecular C-H⋯O and π-π stacking inter-actions [centroid-centroid distance = 3.7838 (3) Å].

Related literature

For the use of co-crystallization reactions in developing new methodologies in supra­molecular synthesis, see: Desiraju (2003 ▶); Shan et al. (2002 ▶). For hydrogen bonding and π–π stacking in mol­ecular synthesis, see: Shattock et al. (2005 ▶). For a related structure, see: Ma et al. (2006 ▶). An independent determination of this structure is reported in the preceeding paper (Li et al., 2008 ▶).

Experimental

Crystal data

C13H14N2·C14H10O5

M = 456.48

Triclinic,

a = 6.8927 (12) Å

b = 11.5788 (19) Å

c = 14.974 (3) Å

α = 86.638 (3)°

β = 81.205 (3)°

γ = 73.963 (3)°

V = 1134.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.38 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.966, T max = 0.985

5767 measured reflections

3965 independent reflections

1530 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.232

S = 1.01

3965 reflections

309 parameters

H-atom parameters constrained

Δρmax = 0.64 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034971/fl2224sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034971/fl2224Isup2.hkl

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

C27H24N2O5	Z = 2
Mr = 456.48	F000 = 480
Triclinic, P1	Dx = 1.336 Mg m−3
a = 6.8927 (12) Å	Mo Kα radiation λ = 0.71073 Å
b = 11.5788 (19) Å	θ = 1.8–25.1º
c = 14.974 (3) Å	µ = 0.09 mm−1
α = 86.638 (3)º	T = 293 (2) K
β = 81.205 (3)º	Prism, colorless
γ = 73.963 (3)º	0.38 × 0.20 × 0.16 mm
V = 1134.9 (3) Å3

Bruker SMART CCD diffractometer	3965 independent reflections
Radiation source: fine-focus sealed tube	1530 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.034
T = 293(2) K	θmax = 25.1º
φ and ω scans	θmin = 1.8º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)	h = −4→8
Tmin = 0.966, Tmax = 0.985	k = −11→13
5767 measured reflections	l = −17→17

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)] = 0.074	H-atom parameters constrained
wR(F2) = 0.232	w = 1/[σ2(Fo2) + (0.09P)2 + 0.05P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3965 reflections	Δρmax = 0.64 e Å−3
309 parameters	Δρmin = −0.22 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	−0.1091 (7)	−0.1160 (4)	0.5739 (3)	0.0694 (12)
N2	0.6798 (6)	0.1948 (4)	0.9734 (2)	0.0664 (12)
O1	0.6076 (5)	0.3326 (3)	0.2752 (2)	0.0738 (10)
O2	−0.0318 (6)	0.1895 (3)	0.0761 (2)	0.0776 (11)
H2	−0.1262	0.1911	0.0483	0.116*
O3	−0.1240 (6)	0.3872 (3)	0.0493 (2)	0.0835 (12)
O4	0.5299 (6)	0.7923 (3)	0.5091 (3)	0.0970 (13)
O5	0.8627 (5)	0.7071 (3)	0.4860 (3)	0.0918 (12)
H5	0.8652	0.7642	0.5152	0.138*
C1	0.6402 (8)	0.1023 (4)	0.9399 (3)	0.0731 (15)
H1	0.7252	0.0259	0.9485	0.088*
C2	0.4779 (8)	0.1132 (4)	0.8923 (3)	0.0720 (15)
H2A	0.4552	0.0449	0.8711	0.086*
C3	0.3505 (7)	0.2248 (4)	0.8766 (3)	0.0563 (12)
C4	0.3945 (7)	0.3207 (4)	0.9109 (3)	0.0665 (14)
H4	0.3132	0.3982	0.9026	0.080*
C5	0.5569 (8)	0.3026 (4)	0.9570 (3)	0.0717 (15)
H5A	0.5836	0.3696	0.9783	0.086*
C6	0.1679 (7)	0.2448 (4)	0.8272 (3)	0.0726 (15)
H6A	0.0457	0.2712	0.8707	0.087*
H6B	0.1705	0.3100	0.7837	0.087*
C7	0.1503 (7)	0.1392 (4)	0.7780 (3)	0.0723 (15)
H7A	0.1395	0.0749	0.8213	0.087*
H7B	0.2735	0.1103	0.7355	0.087*
C8	−0.0324 (7)	0.1698 (4)	0.7273 (3)	0.0658 (14)
H8A	−0.1547	0.1987	0.7703	0.079*
H8B	−0.0214	0.2351	0.6849	0.079*
C9	−0.0580 (7)	0.0684 (4)	0.6761 (3)	0.0579 (13)
C10	−0.2435 (7)	0.0733 (4)	0.6501 (3)	0.0617 (13)
H10	−0.3557	0.1381	0.6664	0.074*
C11	−0.2627 (8)	−0.0177 (5)	0.6000 (3)	0.0684 (14)
H11	−0.3895	−0.0112	0.5829	0.082*
C12	0.0675 (8)	−0.1175 (4)	0.5988 (3)	0.0741 (15)
H12	0.1782	−0.1829	0.5818	0.089*
C13	0.1000 (8)	−0.0295 (4)	0.6480 (3)	0.0710 (15)
H13	0.2295	−0.0365	0.6622	0.085*
C14	0.1947 (7)	0.4155 (4)	0.1356 (3)	0.0669 (14)
H14	0.1244	0.4808	0.1035	0.080*
C15	0.3456 (8)	0.4285 (4)	0.1817 (3)	0.0679 (14)
H15	0.3811	0.5007	0.1787	0.081*
C16	0.4428 (7)	0.3329 (4)	0.2322 (3)	0.0600 (13)
C17	0.3950 (7)	0.2251 (4)	0.2337 (3)	0.0686 (15)
H17	0.4633	0.1602	0.2668	0.082*
C18	0.2452 (7)	0.2132 (4)	0.1858 (3)	0.0642 (14)
H18	0.2123	0.1403	0.1876	0.077*
C19	0.1451 (7)	0.3072 (4)	0.1360 (3)	0.0520 (12)
C20	−0.0181 (8)	0.3011 (5)	0.0835 (3)	0.0645 (14)
C21	0.6111 (8)	0.4317 (4)	0.3224 (3)	0.0572 (12)
C22	0.4418 (8)	0.5167 (4)	0.3598 (3)	0.0655 (14)
H22	0.3126	0.5129	0.3518	0.079*
C23	0.4631 (7)	0.6079 (4)	0.4093 (3)	0.0618 (13)
H23	0.3483	0.6667	0.4336	0.074*
C24	0.6554 (7)	0.6123 (4)	0.4232 (3)	0.0533 (12)
C25	0.8227 (7)	0.5255 (4)	0.3868 (3)	0.0659 (14)
H25	0.9519	0.5276	0.3962	0.079*
C26	0.8021 (7)	0.4350 (4)	0.3364 (3)	0.0656 (13)
H26	0.9168	0.3763	0.3120	0.079*
C27	0.6727 (9)	0.7134 (5)	0.4775 (3)	0.0678 (14)

	U11	U22	U33	U12	U13	U23
N1	0.055 (3)	0.088 (3)	0.072 (3)	−0.025 (3)	−0.024 (2)	0.011 (2)
N2	0.069 (3)	0.065 (3)	0.075 (3)	−0.024 (2)	−0.024 (2)	−0.006 (2)
O1	0.070 (2)	0.069 (2)	0.090 (3)	−0.0147 (18)	−0.036 (2)	−0.0197 (18)
O2	0.090 (3)	0.060 (2)	0.098 (3)	−0.0266 (19)	−0.045 (2)	−0.0052 (17)
O3	0.088 (3)	0.066 (2)	0.105 (3)	−0.015 (2)	−0.055 (2)	0.007 (2)
O4	0.073 (3)	0.086 (3)	0.132 (3)	−0.001 (2)	−0.034 (3)	−0.050 (2)
O5	0.071 (3)	0.096 (3)	0.119 (3)	−0.026 (2)	−0.027 (2)	−0.041 (2)
C1	0.084 (4)	0.060 (3)	0.086 (4)	−0.025 (3)	−0.032 (3)	−0.002 (3)
C2	0.086 (4)	0.061 (3)	0.082 (4)	−0.027 (3)	−0.035 (3)	−0.005 (3)
C3	0.058 (3)	0.056 (3)	0.058 (3)	−0.019 (3)	−0.011 (3)	−0.011 (2)
C4	0.058 (3)	0.057 (3)	0.087 (4)	−0.013 (3)	−0.019 (3)	−0.013 (3)
C5	0.073 (4)	0.059 (3)	0.089 (4)	−0.019 (3)	−0.022 (3)	−0.015 (3)
C6	0.068 (4)	0.072 (3)	0.083 (4)	−0.021 (3)	−0.020 (3)	−0.014 (3)
C7	0.074 (4)	0.074 (3)	0.080 (4)	−0.027 (3)	−0.026 (3)	−0.013 (3)
C8	0.062 (3)	0.072 (3)	0.069 (3)	−0.018 (3)	−0.025 (3)	−0.012 (3)
C9	0.058 (4)	0.067 (3)	0.053 (3)	−0.018 (3)	−0.020 (3)	−0.004 (2)
C10	0.059 (4)	0.059 (3)	0.071 (3)	−0.012 (3)	−0.026 (3)	−0.008 (2)
C11	0.054 (4)	0.080 (3)	0.079 (4)	−0.019 (3)	−0.032 (3)	−0.001 (3)
C12	0.062 (4)	0.071 (3)	0.084 (4)	−0.007 (3)	−0.008 (3)	−0.019 (3)
C13	0.055 (4)	0.075 (3)	0.085 (4)	−0.010 (3)	−0.021 (3)	−0.026 (3)
C14	0.078 (4)	0.059 (3)	0.070 (3)	−0.019 (3)	−0.030 (3)	−0.001 (2)
C15	0.079 (4)	0.063 (3)	0.077 (4)	−0.033 (3)	−0.029 (3)	−0.003 (3)
C16	0.066 (4)	0.059 (3)	0.062 (3)	−0.018 (3)	−0.024 (3)	−0.009 (2)
C17	0.075 (4)	0.056 (3)	0.080 (4)	−0.012 (3)	−0.034 (3)	−0.005 (3)
C18	0.074 (4)	0.047 (3)	0.080 (4)	−0.021 (3)	−0.027 (3)	−0.003 (2)
C19	0.055 (3)	0.050 (3)	0.055 (3)	−0.016 (2)	−0.014 (2)	−0.010 (2)
C20	0.066 (4)	0.063 (3)	0.071 (4)	−0.022 (3)	−0.019 (3)	−0.007 (3)
C21	0.062 (4)	0.058 (3)	0.059 (3)	−0.021 (3)	−0.021 (3)	−0.002 (2)
C22	0.049 (3)	0.079 (3)	0.075 (4)	−0.021 (3)	−0.019 (3)	−0.009 (3)
C23	0.056 (3)	0.060 (3)	0.068 (3)	−0.002 (3)	−0.026 (3)	−0.011 (2)
C24	0.057 (3)	0.060 (3)	0.050 (3)	−0.020 (3)	−0.017 (3)	−0.005 (2)
C25	0.050 (3)	0.078 (3)	0.075 (4)	−0.024 (3)	−0.008 (3)	−0.020 (3)
C26	0.047 (3)	0.072 (3)	0.076 (4)	−0.009 (3)	−0.010 (3)	−0.018 (3)
C27	0.065 (4)	0.070 (4)	0.075 (4)	−0.019 (3)	−0.025 (3)	−0.007 (3)

N1—C12	1.321 (6)	C9—C13	1.372 (6)
N1—C11	1.352 (6)	C9—C10	1.379 (5)
N2—C1	1.320 (5)	C10—C11	1.375 (6)
N2—C5	1.333 (5)	C10—H10	0.9300
O1—C16	1.387 (5)	C11—H11	0.9300
O1—C21	1.390 (5)	C12—C13	1.376 (6)
O2—C20	1.333 (5)	C12—H12	0.9300
O2—H2	0.8200	C13—H13	0.9300
O3—C20	1.201 (5)	C14—C15	1.378 (6)
O4—C27	1.200 (5)	C14—C19	1.387 (5)
O5—C27	1.317 (6)	C14—H14	0.9300
O5—H5	0.8200	C15—C16	1.376 (6)
C1—C2	1.388 (6)	C15—H15	0.9300
C1—H1	0.9300	C16—C17	1.374 (6)
C2—C3	1.377 (6)	C17—C18	1.384 (6)
C2—H2A	0.9300	C17—H17	0.9300
C3—C4	1.374 (5)	C18—C19	1.365 (6)
C3—C6	1.513 (6)	C18—H18	0.9300
C4—C5	1.365 (6)	C19—C20	1.487 (6)
C4—H4	0.9300	C21—C22	1.369 (6)
C5—H5A	0.9300	C21—C26	1.375 (6)
C6—C7	1.505 (5)	C22—C23	1.378 (5)
C6—H6A	0.9700	C22—H22	0.9300
C6—H6B	0.9700	C23—C24	1.387 (6)
C7—C8	1.518 (6)	C23—H23	0.9300
C7—H7A	0.9700	C24—C25	1.367 (6)
C7—H7B	0.9700	C24—C27	1.505 (6)
C8—C9	1.502 (5)	C25—C26	1.377 (6)
C8—H8A	0.9700	C25—H25	0.9300
C8—H8B	0.9700	C26—H26	0.9300
C12—N1—C11	114.4 (4)	N1—C12—H12	117.5
C1—N2—C5	116.0 (4)	C13—C12—H12	117.5
C16—O1—C21	121.5 (4)	C9—C13—C12	120.3 (5)
C20—O2—H2	109.5	C9—C13—H13	119.9
C27—O5—H5	109.5	C12—C13—H13	119.9
N2—C1—C2	123.2 (5)	C15—C14—C19	121.6 (4)
N2—C1—H1	118.4	C15—C14—H14	119.2
C2—C1—H1	118.4	C19—C14—H14	119.2
C3—C2—C1	120.3 (4)	C16—C15—C14	118.8 (4)
C3—C2—H2A	119.9	C16—C15—H15	120.6
C1—C2—H2A	119.9	C14—C15—H15	120.6
C4—C3—C2	116.0 (4)	C17—C16—C15	120.3 (4)
C4—C3—C6	120.2 (4)	C17—C16—O1	115.6 (4)
C2—C3—C6	123.8 (4)	C15—C16—O1	123.7 (4)
C5—C4—C3	120.2 (4)	C16—C17—C18	120.0 (4)
C5—C4—H4	119.9	C16—C17—H17	120.0
C3—C4—H4	119.9	C18—C17—H17	120.0
N2—C5—C4	124.2 (4)	C19—C18—C17	120.7 (4)
N2—C5—H5A	117.9	C19—C18—H18	119.6
C4—C5—H5A	117.9	C17—C18—H18	119.6
C7—C6—C3	116.9 (4)	C18—C19—C14	118.5 (4)
C7—C6—H6A	108.1	C18—C19—C20	123.6 (4)
C3—C6—H6A	108.1	C14—C19—C20	117.9 (4)
C7—C6—H6B	108.1	O3—C20—O2	123.2 (4)
C3—C6—H6B	108.1	O3—C20—C19	123.7 (5)
H6A—C6—H6B	107.3	O2—C20—C19	113.1 (4)
C6—C7—C8	112.9 (4)	C22—C21—C26	120.2 (4)
C6—C7—H7A	109.0	C22—C21—O1	124.9 (4)
C8—C7—H7A	109.0	C26—C21—O1	114.7 (4)
C6—C7—H7B	109.0	C21—C22—C23	119.9 (4)
C8—C7—H7B	109.0	C21—C22—H22	120.0
H7A—C7—H7B	107.8	C23—C22—H22	120.0
C9—C8—C7	115.6 (4)	C22—C23—C24	120.2 (4)
C9—C8—H8A	108.4	C22—C23—H23	119.9
C7—C8—H8A	108.4	C24—C23—H23	119.9
C9—C8—H8B	108.4	C25—C24—C23	119.2 (4)
C7—C8—H8B	108.4	C25—C24—C27	122.1 (4)
H8A—C8—H8B	107.4	C23—C24—C27	118.7 (5)
C13—C9—C10	116.1 (4)	C24—C25—C26	120.8 (4)
C13—C9—C8	123.2 (4)	C24—C25—H25	119.6
C10—C9—C8	120.6 (4)	C26—C25—H25	119.6
C11—C10—C9	120.1 (4)	C21—C26—C25	119.7 (5)
C11—C10—H10	120.0	C21—C26—H26	120.1
C9—C10—H10	120.0	C25—C26—H26	120.1
N1—C11—C10	124.2 (4)	O4—C27—O5	123.2 (5)
N1—C11—H11	117.9	O4—C27—C24	124.1 (5)
C10—C11—H11	117.9	O5—C27—C24	112.7 (5)
N1—C12—C13	125.0 (5)
C5—N2—C1—C2	−1.8 (7)	C15—C16—C17—C18	−1.5 (8)
N2—C1—C2—C3	1.2 (8)	O1—C16—C17—C18	−174.2 (4)
C1—C2—C3—C4	−0.4 (7)	C16—C17—C18—C19	0.8 (8)
C1—C2—C3—C6	−178.7 (5)	C17—C18—C19—C14	−1.0 (7)
C2—C3—C4—C5	0.4 (7)	C17—C18—C19—C20	−179.6 (4)
C6—C3—C4—C5	178.8 (4)	C15—C14—C19—C18	2.1 (7)
C1—N2—C5—C4	1.8 (7)	C15—C14—C19—C20	−179.3 (4)
C3—C4—C5—N2	−1.1 (8)	C18—C19—C20—O3	170.0 (5)
C4—C3—C6—C7	169.8 (4)	C14—C19—C20—O3	−8.5 (7)
C2—C3—C6—C7	−11.9 (7)	C18—C19—C20—O2	−11.6 (7)
C3—C6—C7—C8	−177.5 (4)	C14—C19—C20—O2	169.8 (4)
C6—C7—C8—C9	179.6 (4)	C16—O1—C21—C22	24.9 (7)
C7—C8—C9—C13	−23.0 (7)	C16—O1—C21—C26	−160.3 (4)
C7—C8—C9—C10	160.9 (4)	C26—C21—C22—C23	2.0 (7)
C13—C9—C10—C11	0.9 (7)	O1—C21—C22—C23	176.6 (4)
C8—C9—C10—C11	177.2 (4)	C21—C22—C23—C24	−1.5 (7)
C12—N1—C11—C10	−1.6 (7)	C22—C23—C24—C25	0.2 (7)
C9—C10—C11—N1	0.8 (7)	C22—C23—C24—C27	179.9 (4)
C11—N1—C12—C13	0.8 (7)	C23—C24—C25—C26	0.5 (7)
C10—C9—C13—C12	−1.7 (7)	C27—C24—C25—C26	−179.2 (4)
C8—C9—C13—C12	−177.9 (4)	C22—C21—C26—C25	−1.3 (7)
N1—C12—C13—C9	0.9 (8)	O1—C21—C26—C25	−176.4 (4)
C19—C14—C15—C16	−2.8 (8)	C24—C25—C26—C21	0.0 (7)
C14—C15—C16—C17	2.4 (8)	C25—C24—C27—O4	178.6 (5)
C14—C15—C16—O1	174.5 (4)	C23—C24—C27—O4	−1.1 (8)
C21—O1—C16—C17	−144.3 (4)	C25—C24—C27—O5	−0.5 (7)
C21—O1—C16—C15	43.3 (7)	C23—C24—C27—O5	179.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2i	0.82	1.86	2.679 (5)	174
O5—H5···N1ii	0.82	1.75	2.566 (5)	175
C4—H4···O3iii	0.93	2.55	3.418 (6)	155
C5—H5A···O3iv	0.93	2.48	3.160 (6)	130
C12—H12···O4v	0.93	2.45	3.174 (7)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2i	0.82	1.86	2.679 (5)	174
O5—H5⋯N1ii	0.82	1.75	2.566 (5)	175
C4—H4⋯O3iii	0.93	2.55	3.418 (6)	155
C5—H5A⋯O3iv	0.93	2.48	3.160 (6)	130
C12—H12⋯O4v	0.93	2.45	3.174 (7)	135

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .