4,4'-Bipyrid-yl-4,4'-(hy-droxy-methyl-ene)dibenzoic acid (1/1).

In the title 1:1 co-crystal, C(10)H(8)N(2)·C(15)H(12)O(5), strong inter-molecular O-H⋯N hydrogen bonds link alternating mol-ecules of 4,4'-(hy-droxy-methyl-ene)dibenzoic acid and 4,4'-bipyridyl into zigzag chains in [501]. The crystal packing also exhibits π-π inter-actions between the 4,4'-bipyridyl rings of neighbouring chains [centroid-centroid distance = 3.608 (3) Å] and weak C-H⋯O hydrogen bonds.

Related literature

For background to supra­molecular crystal engineering, see: Simon & Bassoul (2000 ▶). For aromatic carb­oxy­lic acids as supra­molecular synthons, see: Desiraju (1995 ▶). For studies of bent arenedicarboxyl­ate ligands, see: Koichi et al. (2011 ▶); Xu et al. (2011 ▶).

Experimental

Crystal data

C10H8N2·C15H12O5

M = 428.43

Monoclinic,

a = 8.0528 (16) Å

b = 11.683 (2) Å

c = 21.922 (4) Å

β = 96.66 (3)°

V = 2048.6 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.31 × 0.14 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.984, T max = 0.988

16322 measured reflections

3800 independent reflections

1903 reflections with I > 2σ(I)

R int = 0.089

Refinement

R[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.210

S = 0.99

3800 reflections

298 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.68 e Å−3

Δρmin = −0.28 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); 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: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812011956/cv5265sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011956/cv5265Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011956/cv5265Isup3.cml

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

C10H8N2·C15H12O5	F(000) = 896
Mr = 428.43	Dx = 1.389 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2687 reflections
a = 8.0528 (16) Å	θ = 3.1–25.5°
b = 11.683 (2) Å	µ = 0.10 mm−1
c = 21.922 (4) Å	T = 298 K
β = 96.66 (3)°	Block, colourless
V = 2048.6 (7) Å3	0.31 × 0.14 × 0.12 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	3800 independent reflections
Radiation source: fine-focus sealed tube	1903 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.089
Detector resolution: 0 pixels mm-1	θmax = 25.5°, θmin = 3.1°
ω scans	h = −9→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −14→14
Tmin = 0.984, Tmax = 0.988	l = −26→24
16322 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)] = 0.077	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.210	w = 1/[σ2(Fo2) + (0.0824P)2 + 1.4919P] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max < 0.001
3800 reflections	Δρmax = 0.68 e Å−3
298 parameters	Δρmin = −0.28 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 (18)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	1.7007 (4)	−0.0589 (3)	0.44854 (15)	0.0828 (10)
O2	1.8293 (4)	−0.0048 (3)	0.36999 (15)	0.0844 (11)
O3	0.6425 (4)	−0.0831 (3)	0.12982 (16)	0.0831 (10)
O4	0.5017 (4)	0.0793 (3)	0.11948 (17)	0.0863 (12)
O5	1.1910 (4)	0.3660 (3)	0.2676 (2)	0.1155 (15)
H5A	1.1098	0.4045	0.2542	0.173*
N1	−0.2656 (4)	0.0472 (3)	−0.06295 (16)	0.0628 (10)
N2	0.4192 (4)	0.3635 (3)	0.08219 (19)	0.0694 (10)
C1	1.7018 (5)	−0.0067 (4)	0.4015 (2)	0.0610 (11)
C2	1.5595 (5)	0.0650 (4)	0.37421 (18)	0.0557 (11)
C3	1.5610 (5)	0.1201 (4)	0.31932 (19)	0.0686 (13)
H3A	1.6546	0.1139	0.2984	0.082*
C4	1.4188 (5)	0.0754 (4)	0.40432 (19)	0.0633 (12)
H4A	1.4142	0.0385	0.4417	0.076*
C5	1.4258 (5)	0.1850 (5)	0.2941 (2)	0.0780 (15)
H5B	1.4302	0.2220	0.2568	0.094*
C6	1.2844 (5)	0.1406 (4)	0.3790 (2)	0.0668 (12)
H6A	1.1908	0.1475	0.3999	0.080*
C7	1.2865 (5)	0.1952 (4)	0.3238 (2)	0.0653 (12)
C8	1.1347 (5)	0.2650 (4)	0.2987 (2)	0.0784 (15)
H8A	1.0768	0.2904	0.3332	0.094*
C9	1.0110 (4)	0.1983 (4)	0.25372 (18)	0.0586 (11)
C10	1.0175 (5)	0.0821 (4)	0.24747 (19)	0.0660 (12)
H10A	1.1054	0.0415	0.2686	0.079*
C11	0.8944 (5)	0.0235 (4)	0.20995 (19)	0.0613 (11)
H11A	0.9000	−0.0557	0.2064	0.074*
C12	0.7646 (4)	0.0829 (4)	0.17821 (17)	0.0526 (10)
C13	0.7589 (5)	0.1998 (4)	0.18338 (18)	0.0608 (11)
H13A	0.6723	0.2404	0.1614	0.073*
C14	0.8806 (5)	0.2575 (4)	0.22089 (19)	0.0618 (11)
H14A	0.8752	0.3368	0.2242	0.074*
C15	0.6312 (5)	0.0179 (4)	0.1404 (2)	0.0616 (11)
C16	−0.2813 (5)	0.1129 (4)	−0.0146 (2)	0.0671 (12)
H16A	−0.3849	0.1154	0.0003	0.081*
C17	−0.1537 (5)	0.1778 (4)	0.01501 (19)	0.0594 (11)
H17A	−0.1712	0.2220	0.0489	0.071*
C18	0.0024 (4)	0.1760 (3)	−0.00674 (18)	0.0515 (10)
C19	0.0182 (5)	0.1095 (3)	−0.05812 (18)	0.0578 (11)
H19A	0.1191	0.1070	−0.0748	0.069*
C20	−0.1179 (5)	0.0466 (4)	−0.0844 (2)	0.0641 (12)
H20A	−0.1051	0.0020	−0.1187	0.077*
C21	0.1463 (5)	0.2406 (3)	0.02397 (18)	0.0526 (10)
C22	0.1556 (5)	0.2692 (4)	0.0859 (2)	0.0649 (12)
H22A	0.0711	0.2478	0.1091	0.078*
C23	0.2930 (5)	0.3303 (4)	0.1123 (2)	0.0725 (13)
H23A	0.2973	0.3492	0.1536	0.087*
C24	0.4097 (5)	0.3339 (4)	0.0235 (2)	0.0679 (13)
H24A	0.4970	0.3555	0.0017	0.082*
C25	0.2790 (5)	0.2731 (4)	−0.0073 (2)	0.0631 (12)
H25A	0.2798	0.2542	−0.0484	0.076*
H2	1.915 (6)	−0.042 (5)	0.385 (2)	0.100 (19)*
H1	0.436 (7)	0.031 (5)	0.099 (2)	0.11 (2)*

	U11	U22	U33	U12	U13	U23
O1	0.084 (2)	0.091 (3)	0.071 (2)	0.0073 (18)	0.0029 (17)	0.0258 (19)
O2	0.061 (2)	0.109 (3)	0.082 (2)	0.023 (2)	0.0036 (18)	0.026 (2)
O3	0.0630 (19)	0.078 (3)	0.105 (3)	−0.0035 (17)	−0.0046 (17)	−0.008 (2)
O4	0.062 (2)	0.083 (3)	0.106 (3)	0.0024 (18)	−0.0254 (19)	−0.017 (2)
O5	0.089 (3)	0.090 (3)	0.156 (4)	−0.001 (2)	−0.033 (2)	0.012 (3)
N1	0.053 (2)	0.064 (2)	0.068 (2)	0.0002 (17)	−0.0067 (18)	−0.0012 (19)
N2	0.054 (2)	0.068 (3)	0.083 (3)	−0.0012 (18)	−0.007 (2)	−0.005 (2)
C1	0.057 (3)	0.068 (3)	0.057 (3)	−0.005 (2)	−0.002 (2)	−0.001 (2)
C2	0.051 (2)	0.064 (3)	0.051 (2)	−0.0029 (19)	0.0005 (19)	0.000 (2)
C3	0.053 (2)	0.095 (4)	0.058 (3)	0.014 (2)	0.009 (2)	0.012 (3)
C4	0.066 (3)	0.073 (3)	0.050 (2)	−0.013 (2)	0.007 (2)	−0.004 (2)
C5	0.064 (3)	0.109 (4)	0.060 (3)	0.015 (3)	0.002 (2)	0.015 (3)
C6	0.047 (2)	0.085 (3)	0.070 (3)	−0.001 (2)	0.010 (2)	−0.020 (3)
C7	0.052 (2)	0.079 (3)	0.063 (3)	0.002 (2)	−0.007 (2)	−0.015 (2)
C8	0.063 (3)	0.074 (4)	0.094 (4)	0.007 (2)	−0.011 (3)	−0.014 (3)
C9	0.045 (2)	0.071 (3)	0.059 (2)	0.002 (2)	0.0015 (19)	−0.012 (2)
C10	0.051 (2)	0.077 (3)	0.065 (3)	0.010 (2)	−0.011 (2)	−0.007 (2)
C11	0.058 (2)	0.059 (3)	0.064 (3)	0.005 (2)	0.000 (2)	−0.002 (2)
C12	0.044 (2)	0.064 (3)	0.049 (2)	−0.0003 (19)	0.0033 (17)	0.001 (2)
C13	0.048 (2)	0.074 (3)	0.058 (2)	0.006 (2)	−0.0040 (19)	0.000 (2)
C14	0.056 (2)	0.061 (3)	0.066 (3)	0.003 (2)	−0.001 (2)	−0.003 (2)
C15	0.055 (3)	0.064 (3)	0.065 (3)	0.001 (2)	0.001 (2)	−0.001 (2)
C16	0.047 (2)	0.068 (3)	0.086 (3)	0.001 (2)	0.005 (2)	−0.002 (3)
C17	0.054 (2)	0.061 (3)	0.062 (3)	0.003 (2)	0.001 (2)	−0.002 (2)
C18	0.048 (2)	0.051 (3)	0.053 (2)	0.0009 (18)	−0.0034 (18)	0.005 (2)
C19	0.053 (2)	0.059 (3)	0.059 (3)	0.003 (2)	−0.001 (2)	0.002 (2)
C20	0.063 (3)	0.066 (3)	0.060 (3)	0.003 (2)	−0.005 (2)	−0.003 (2)
C21	0.049 (2)	0.051 (3)	0.055 (2)	0.0005 (18)	−0.0044 (19)	0.0004 (19)
C22	0.056 (2)	0.065 (3)	0.071 (3)	0.000 (2)	−0.006 (2)	−0.004 (2)
C23	0.066 (3)	0.076 (3)	0.071 (3)	0.006 (2)	−0.012 (2)	−0.009 (3)
C24	0.052 (2)	0.070 (3)	0.080 (3)	−0.003 (2)	−0.002 (2)	0.004 (3)
C25	0.057 (2)	0.069 (3)	0.062 (3)	−0.003 (2)	0.000 (2)	0.003 (2)

O1—C1	1.199 (5)	C9—C14	1.387 (5)
O2—C1	1.302 (5)	C10—C11	1.392 (5)
O2—H2	0.84 (5)	C10—H10A	0.9300
O3—C15	1.208 (5)	C11—C12	1.375 (5)
O4—C15	1.304 (5)	C11—H11A	0.9300
O4—H1	0.87 (6)	C12—C13	1.371 (6)
O5—C8	1.460 (6)	C12—C15	1.487 (6)
O5—H5A	0.8200	C13—C14	1.380 (5)
N1—C16	1.327 (5)	C13—H13A	0.9300
N1—C20	1.329 (5)	C14—H14A	0.9300
N2—C24	1.325 (6)	C16—C17	1.377 (5)
N2—C23	1.332 (6)	C16—H16A	0.9300
C1—C2	1.488 (6)	C17—C18	1.395 (5)
C2—C3	1.365 (5)	C17—H17A	0.9300
C2—C4	1.381 (6)	C18—C19	1.386 (5)
C3—C5	1.388 (6)	C18—C21	1.478 (5)
C3—H3A	0.9300	C19—C20	1.387 (5)
C4—C6	1.386 (6)	C19—H19A	0.9300
C4—H4A	0.9300	C20—H20A	0.9300
C5—C7	1.365 (6)	C21—C25	1.387 (6)
C5—H5B	0.9300	C21—C22	1.391 (5)
C6—C7	1.370 (6)	C22—C23	1.385 (6)
C6—H6A	0.9300	C22—H22A	0.9300
C7—C8	1.518 (6)	C23—H23A	0.9300
C8—C9	1.531 (6)	C24—C25	1.379 (6)
C8—H8A	0.9800	C24—H24A	0.9300
C9—C10	1.367 (6)	C25—H25A	0.9300
C1—O2—H2	116 (4)	C13—C12—C15	121.7 (4)
C15—O4—H1	104 (4)	C11—C12—C15	118.8 (4)
C8—O5—H5A	109.5	C12—C13—C14	120.5 (4)
C16—N1—C20	117.2 (4)	C12—C13—H13A	119.7
C24—N2—C23	116.3 (4)	C14—C13—H13A	119.7
O1—C1—O2	123.3 (4)	C13—C14—C9	120.5 (4)
O1—C1—C2	123.3 (4)	C13—C14—H14A	119.7
O2—C1—C2	113.3 (4)	C9—C14—H14A	119.7
C3—C2—C4	118.1 (4)	O3—C15—O4	123.0 (4)
C3—C2—C1	122.3 (4)	O3—C15—C12	122.7 (4)
C4—C2—C1	119.6 (4)	O4—C15—C12	114.3 (4)
C2—C3—C5	121.4 (4)	N1—C16—C17	124.0 (4)
C2—C3—H3A	119.3	N1—C16—H16A	118.0
C5—C3—H3A	119.3	C17—C16—H16A	118.0
C2—C4—C6	120.2 (4)	C16—C17—C18	118.9 (4)
C2—C4—H4A	119.9	C16—C17—H17A	120.5
C6—C4—H4A	119.9	C18—C17—H17A	120.5
C7—C5—C3	120.6 (4)	C19—C18—C17	117.2 (4)
C7—C5—H5B	119.7	C19—C18—C21	121.0 (4)
C3—C5—H5B	119.7	C17—C18—C21	121.8 (4)
C7—C6—C4	121.4 (4)	C18—C19—C20	119.5 (4)
C7—C6—H6A	119.3	C18—C19—H19A	120.3
C4—C6—H6A	119.3	C20—C19—H19A	120.3
C5—C7—C6	118.3 (4)	N1—C20—C19	123.1 (4)
C5—C7—C8	123.1 (5)	N1—C20—H20A	118.4
C6—C7—C8	118.5 (4)	C19—C20—H20A	118.4
O5—C8—C7	108.8 (4)	C25—C21—C22	117.3 (4)
O5—C8—C9	108.9 (4)	C25—C21—C18	121.6 (4)
C7—C8—C9	113.3 (4)	C22—C21—C18	121.2 (4)
O5—C8—H8A	108.6	C23—C22—C21	118.8 (4)
C7—C8—H8A	108.6	C23—C22—H22A	120.6
C9—C8—H8A	108.6	C21—C22—H22A	120.6
C10—C9—C14	118.6 (4)	N2—C23—C22	124.1 (5)
C10—C9—C8	122.7 (4)	N2—C23—H23A	117.9
C14—C9—C8	118.5 (4)	C22—C23—H23A	117.9
C9—C10—C11	121.0 (4)	N2—C24—C25	124.3 (4)
C9—C10—H10A	119.5	N2—C24—H24A	117.8
C11—C10—H10A	119.5	C25—C24—H24A	117.8
C12—C11—C10	119.9 (4)	C24—C25—C21	119.2 (4)
C12—C11—H11A	120.1	C24—C25—H25A	120.4
C10—C11—H11A	120.1	C21—C25—H25A	120.4
C13—C12—C11	119.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2i	0.84 (5)	1.82 (5)	2.660 (5)	173 (5)
O4—H1···N1ii	0.87 (6)	1.76 (6)	2.605 (5)	166 (5)
C19—H19A···O3iii	0.93	2.40	3.321 (5)	171
C17—H17A···O1iv	0.93	2.57	3.212 (5)	126
C8—H8A···O3iv	0.98	2.51	3.376 (6)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2i	0.84 (5)	1.82 (5)	2.660 (5)	173 (5)
O4—H1⋯N1ii	0.87 (6)	1.76 (6)	2.605 (5)	166 (5)
C19—H19A⋯O3iii	0.93	2.40	3.321 (5)	171
C17—H17A⋯O1iv	0.93	2.57	3.212 (5)	126
C8—H8A⋯O3iv	0.98	2.51	3.376 (6)	148

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