4-(2-Carboxy-benzo-yl)benzoic acid-4,4'-bipyridine (1/1).

In the heteromolecular title compound, C(15)H(10)O(5)·C(10)H(8)N(2), the two components are linked by O-H⋯N hydrogen bonds to form four-component ring supra-molecular assemblies. These are further inter-connected with neighbouring mol-ecules by weak inter-molecular C-H⋯π inter-actions and C-H⋯O hydrogen bonds to generate a three-dimensional network.

Related literature

For details of the C—H⋯O hydrogen bond, see: Bhogala et al. (2005 ▶); Wang et al. (2008 ▶). For details of the C—H⋯π inter­action, see: Fun & Kia (2008 ▶).

Experimental

Crystal data

C15H10O5·C10H8N2

M = 426.41

Monoclinic,

a = 7.6883 (6) Å

b = 24.1886 (18) Å

c = 10.9560 (8) Å

β = 95.873 (1)°

V = 2026.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 (2) K

0.35 × 0.28 × 0.16 mm

Data collection

Bruker CCD area detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.957, T max = 0.984

10190 measured reflections

3607 independent reflections

2177 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.128

S = 1.02

3607 reflections

292 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.17 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/S1600536808037823/si2130sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037823/si2130Isup2.hkl

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

C15H10O5·C10H8N2	F000 = 888
Mr = 426.41	Dx = 1.397 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P2yn	Cell parameters from 1385 reflections
a = 7.6883 (6) Å	θ = 2.5–21.2º
b = 24.1886 (18) Å	µ = 0.10 mm−1
c = 10.9560 (8) Å	T = 296 (2) K
β = 95.8730 (10)º	Block, colorless
V = 2026.8 (3) Å3	0.35 × 0.28 × 0.16 mm
Z = 4

Bruker CCD area detector diffractometer	3607 independent reflections
Radiation source: fine-focus sealed tube	2177 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.041
T = 296(2) K	θmax = 25.1º
φ and ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 1997)	h = −9→9
Tmin = 0.957, Tmax = 0.984	k = −28→28
10190 measured reflections	l = −13→7

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045	w = 1/[σ2(Fo2) + (0.060P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.128	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.21 e Å−3
3607 reflections	Δρmin = −0.17 e Å−3
292 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0131 (14)
Secondary atom site location: difference Fourier map

	x	y	z	Uiso*/Ueq
N1	0.7560 (3)	0.00682 (8)	0.99002 (17)	0.0561 (5)
N2	0.9586 (2)	0.15564 (8)	0.46655 (17)	0.0512 (5)
O1	0.2912 (3)	−0.00260 (8)	0.69911 (15)	0.0779 (6)
O2	0.3035 (3)	0.06365 (7)	0.84053 (15)	0.0671 (5)
H2	0.2837	0.0379	0.8859	0.101*
O3	0.5482 (2)	0.25808 (7)	0.42728 (14)	0.0659 (5)
O4	0.0942 (2)	0.13238 (8)	0.19022 (17)	0.0789 (6)
O5	0.1584 (2)	0.20365 (7)	0.31530 (14)	0.0532 (4)
H5	0.0822	0.1908	0.3541	0.080*
C1	0.9364 (3)	0.18081 (10)	0.5716 (2)	0.0557 (7)
H1	0.9493	0.2190	0.5754	0.067*
C2	0.8955 (3)	0.15357 (10)	0.6751 (2)	0.0530 (6)
H2A	0.8810	0.1733	0.7463	0.064*
C3	0.8761 (3)	0.09687 (9)	0.67290 (19)	0.0426 (5)
C4	0.8951 (3)	0.07078 (10)	0.5629 (2)	0.0521 (6)
H4	0.8804	0.0327	0.5560	0.062*
C5	0.9359 (3)	0.10128 (11)	0.4632 (2)	0.0556 (6)
H5A	0.9480	0.0828	0.3901	0.067*
C6	0.8351 (3)	0.06565 (9)	0.7835 (2)	0.0436 (6)
C7	0.8857 (3)	0.08447 (10)	0.9015 (2)	0.0515 (6)
H7	0.9477	0.1174	0.9134	0.062*
C8	0.8436 (3)	0.05426 (11)	1.0008 (2)	0.0571 (7)
H8	0.8781	0.0677	1.0791	0.069*
C9	0.7071 (3)	−0.01128 (10)	0.8773 (2)	0.0618 (7)
H9	0.6445	−0.0442	0.8682	0.074*
C10	0.7445 (3)	0.01621 (10)	0.7733 (2)	0.0561 (7)
H10	0.7089	0.0016	0.6962	0.067*
C11	0.4552 (3)	0.11251 (9)	0.44658 (19)	0.0472 (6)
H11	0.4816	0.1016	0.3692	0.057*
C12	0.4068 (3)	0.07337 (9)	0.5287 (2)	0.0503 (6)
H12	0.4006	0.0363	0.5060	0.060*
C13	0.3673 (3)	0.08886 (9)	0.64455 (19)	0.0441 (6)
C14	0.3797 (3)	0.14392 (10)	0.6772 (2)	0.0497 (6)
H14	0.3544	0.1548	0.7548	0.060*
C15	0.4293 (3)	0.18291 (9)	0.59573 (19)	0.0481 (6)
H15	0.4392	0.2198	0.6194	0.058*
C16	0.4644 (3)	0.16755 (9)	0.47894 (19)	0.0416 (5)
C17	0.3161 (3)	0.04481 (11)	0.7299 (2)	0.0518 (6)
C18	0.5073 (3)	0.21165 (10)	0.3914 (2)	0.0455 (6)
C19	0.5114 (3)	0.19699 (9)	0.25883 (18)	0.0408 (5)
C20	0.6710 (3)	0.20203 (9)	0.2104 (2)	0.0499 (6)
H20	0.7674	0.2158	0.2592	0.060*
C21	0.6878 (3)	0.18689 (10)	0.0910 (2)	0.0561 (6)
H21	0.7957	0.1898	0.0602	0.067*
C22	0.5460 (3)	0.16750 (10)	0.0174 (2)	0.0565 (7)
H22	0.5575	0.1576	−0.0634	0.068*
C23	0.3861 (3)	0.16268 (9)	0.0633 (2)	0.0499 (6)
H23	0.2902	0.1496	0.0129	0.060*
C24	0.3669 (3)	0.17700 (9)	0.18334 (19)	0.0419 (5)
C25	0.1923 (3)	0.16868 (10)	0.2289 (2)	0.0491 (6)

	U11	U22	U33	U12	U13	U23
N1	0.0681 (14)	0.0556 (14)	0.0461 (12)	0.0026 (11)	0.0131 (10)	0.0071 (10)
N2	0.0492 (12)	0.0565 (14)	0.0486 (12)	−0.0050 (10)	0.0086 (9)	0.0031 (10)
O1	0.1202 (17)	0.0535 (12)	0.0602 (12)	−0.0246 (11)	0.0108 (10)	0.0006 (10)
O2	0.1031 (15)	0.0560 (11)	0.0451 (10)	−0.0019 (10)	0.0217 (10)	0.0098 (8)
O3	0.0921 (14)	0.0547 (12)	0.0515 (11)	−0.0205 (10)	0.0106 (9)	−0.0029 (9)
O4	0.0604 (12)	0.0931 (15)	0.0854 (14)	−0.0297 (11)	0.0174 (10)	−0.0236 (11)
O5	0.0504 (10)	0.0576 (11)	0.0538 (11)	−0.0020 (8)	0.0153 (8)	0.0034 (8)
C1	0.0671 (17)	0.0449 (15)	0.0563 (17)	−0.0067 (12)	0.0129 (13)	0.0014 (12)
C2	0.0642 (16)	0.0476 (15)	0.0489 (15)	−0.0051 (12)	0.0143 (12)	−0.0005 (11)
C3	0.0406 (13)	0.0469 (14)	0.0412 (13)	−0.0016 (10)	0.0077 (10)	0.0003 (11)
C4	0.0633 (16)	0.0447 (14)	0.0505 (15)	−0.0066 (12)	0.0167 (12)	−0.0025 (11)
C5	0.0612 (16)	0.0587 (17)	0.0487 (15)	−0.0053 (13)	0.0149 (12)	−0.0048 (12)
C6	0.0427 (13)	0.0447 (14)	0.0439 (13)	0.0025 (10)	0.0063 (10)	0.0029 (11)
C7	0.0580 (15)	0.0504 (15)	0.0466 (15)	−0.0050 (12)	0.0083 (12)	0.0004 (12)
C8	0.0671 (17)	0.0623 (18)	0.0425 (14)	0.0015 (14)	0.0075 (12)	0.0006 (13)
C9	0.0805 (19)	0.0502 (16)	0.0550 (16)	−0.0103 (13)	0.0090 (14)	0.0087 (13)
C10	0.0767 (18)	0.0499 (16)	0.0413 (14)	−0.0090 (13)	0.0050 (12)	0.0010 (11)
C11	0.0587 (15)	0.0484 (15)	0.0351 (12)	0.0046 (12)	0.0070 (11)	−0.0012 (11)
C12	0.0643 (16)	0.0406 (14)	0.0457 (14)	0.0020 (11)	0.0039 (12)	0.0001 (11)
C13	0.0472 (14)	0.0500 (15)	0.0347 (13)	0.0023 (11)	0.0018 (10)	0.0037 (11)
C14	0.0601 (15)	0.0511 (15)	0.0387 (13)	0.0014 (12)	0.0092 (11)	−0.0031 (11)
C15	0.0606 (15)	0.0421 (14)	0.0421 (14)	−0.0018 (11)	0.0068 (11)	0.0010 (11)
C16	0.0427 (13)	0.0462 (14)	0.0360 (12)	0.0002 (10)	0.0044 (10)	0.0022 (10)
C17	0.0573 (16)	0.0556 (17)	0.0418 (15)	−0.0004 (13)	0.0019 (12)	0.0065 (12)
C18	0.0449 (14)	0.0508 (16)	0.0409 (13)	−0.0018 (11)	0.0054 (10)	0.0017 (11)
C19	0.0438 (13)	0.0427 (13)	0.0365 (12)	−0.0013 (10)	0.0067 (10)	0.0052 (10)
C20	0.0435 (14)	0.0578 (16)	0.0485 (14)	−0.0035 (11)	0.0052 (11)	0.0032 (12)
C21	0.0468 (15)	0.0667 (17)	0.0566 (16)	0.0037 (12)	0.0144 (12)	0.0023 (13)
C22	0.0624 (17)	0.0642 (17)	0.0448 (14)	0.0070 (13)	0.0150 (13)	−0.0036 (12)
C23	0.0516 (15)	0.0510 (15)	0.0461 (14)	−0.0025 (11)	0.0012 (11)	−0.0041 (11)
C24	0.0458 (14)	0.0396 (13)	0.0408 (13)	0.0003 (10)	0.0064 (11)	0.0046 (10)
C25	0.0494 (15)	0.0539 (16)	0.0439 (14)	−0.0026 (12)	0.0041 (11)	0.0024 (12)

N1—C9	1.328 (3)	C9—H9	0.9300
N1—C8	1.330 (3)	C10—H10	0.9300
N2—C5	1.327 (3)	C11—C16	1.378 (3)
N2—C1	1.328 (3)	C11—C12	1.383 (3)
O1—C17	1.205 (3)	C11—H11	0.9300
O2—C17	1.308 (3)	C12—C13	1.387 (3)
O2—H2	0.8200	C12—H12	0.9300
O3—C18	1.220 (3)	C13—C14	1.380 (3)
O4—C25	1.205 (3)	C13—C17	1.497 (3)
O5—C25	1.315 (3)	C14—C15	1.379 (3)
O5—H5	0.8200	C14—H14	0.9300
C1—C2	1.376 (3)	C15—C16	1.385 (3)
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.379 (3)	C16—C18	1.493 (3)
C2—H2A	0.9300	C18—C19	1.499 (3)
C3—C4	1.382 (3)	C19—C20	1.391 (3)
C3—C6	1.489 (3)	C19—C24	1.402 (3)
C4—C5	1.380 (3)	C20—C21	1.377 (3)
C4—H4	0.9300	C20—H20	0.9300
C5—H5A	0.9300	C21—C22	1.371 (3)
C6—C10	1.383 (3)	C21—H21	0.9300
C6—C7	1.388 (3)	C22—C23	1.380 (3)
C7—C8	1.376 (3)	C22—H22	0.9300
C7—H7	0.9300	C23—C24	1.383 (3)
C8—H8	0.9300	C23—H23	0.9300
C9—C10	1.375 (3)	C24—C25	1.493 (3)
C9—N1—C8	117.3 (2)	C14—C13—C12	118.8 (2)
C5—N2—C1	116.7 (2)	C14—C13—C17	122.7 (2)
C17—O2—H2	109.5	C12—C13—C17	118.4 (2)
C25—O5—H5	109.5	C15—C14—C13	120.6 (2)
N2—C1—C2	123.7 (2)	C15—C14—H14	119.7
N2—C1—H1	118.1	C13—C14—H14	119.7
C2—C1—H1	118.1	C14—C15—C16	120.5 (2)
C1—C2—C3	119.7 (2)	C14—C15—H15	119.8
C1—C2—H2A	120.2	C16—C15—H15	119.8
C3—C2—H2A	120.2	C11—C16—C15	119.2 (2)
C2—C3—C4	116.7 (2)	C11—C16—C18	122.3 (2)
C2—C3—C6	121.4 (2)	C15—C16—C18	118.6 (2)
C4—C3—C6	121.9 (2)	O1—C17—O2	124.5 (2)
C5—C4—C3	119.9 (2)	O1—C17—C13	123.2 (2)
C5—C4—H4	120.0	O2—C17—C13	112.3 (2)
C3—C4—H4	120.0	O3—C18—C16	121.2 (2)
N2—C5—C4	123.2 (2)	O3—C18—C19	119.9 (2)
N2—C5—H5A	118.4	C16—C18—C19	118.8 (2)
C4—C5—H5A	118.4	C20—C19—C24	118.8 (2)
C10—C6—C7	116.7 (2)	C20—C19—C18	117.1 (2)
C10—C6—C3	121.3 (2)	C24—C19—C18	124.02 (18)
C7—C6—C3	122.0 (2)	C21—C20—C19	120.7 (2)
C8—C7—C6	119.7 (2)	C21—C20—H20	119.6
C8—C7—H7	120.1	C19—C20—H20	119.6
C6—C7—H7	120.1	C22—C21—C20	120.2 (2)
N1—C8—C7	123.1 (2)	C22—C21—H21	119.9
N1—C8—H8	118.4	C20—C21—H21	119.9
C7—C8—H8	118.4	C21—C22—C23	120.0 (2)
N1—C9—C10	123.3 (2)	C21—C22—H22	120.0
N1—C9—H9	118.4	C23—C22—H22	120.0
C10—C9—H9	118.4	C22—C23—C24	120.7 (2)
C9—C10—C6	119.8 (2)	C22—C23—H23	119.6
C9—C10—H10	120.1	C24—C23—H23	119.6
C6—C10—H10	120.1	C23—C24—C19	119.49 (19)
C16—C11—C12	120.3 (2)	C23—C24—C25	118.1 (2)
C16—C11—H11	119.9	C19—C24—C25	122.33 (19)
C12—C11—H11	119.9	O4—C25—O5	124.0 (2)
C11—C12—C13	120.6 (2)	O4—C25—C24	122.1 (2)
C11—C12—H12	119.7	O5—C25—C24	113.9 (2)
C13—C12—H12	119.7
C5—N2—C1—C2	1.3 (3)	C14—C15—C16—C18	176.4 (2)
N2—C1—C2—C3	0.2 (4)	C14—C13—C17—O1	173.8 (2)
C1—C2—C3—C4	−1.7 (3)	C12—C13—C17—O1	−7.4 (3)
C1—C2—C3—C6	178.9 (2)	C14—C13—C17—O2	−6.8 (3)
C2—C3—C4—C5	1.6 (3)	C12—C13—C17—O2	172.1 (2)
C6—C3—C4—C5	−179.0 (2)	C11—C16—C18—O3	−165.6 (2)
C1—N2—C5—C4	−1.5 (3)	C15—C16—C18—O3	15.8 (3)
C3—C4—C5—N2	0.0 (4)	C11—C16—C18—C19	10.3 (3)
C2—C3—C6—C10	151.9 (2)	C15—C16—C18—C19	−168.35 (19)
C4—C3—C6—C10	−27.6 (3)	O3—C18—C19—C20	59.3 (3)
C2—C3—C6—C7	−28.2 (3)	C16—C18—C19—C20	−116.6 (2)
C4—C3—C6—C7	152.4 (2)	O3—C18—C19—C24	−123.0 (2)
C10—C6—C7—C8	−0.5 (3)	C16—C18—C19—C24	61.1 (3)
C3—C6—C7—C8	179.6 (2)	C24—C19—C20—C21	−0.9 (3)
C9—N1—C8—C7	−0.4 (4)	C18—C19—C20—C21	176.9 (2)
C6—C7—C8—N1	0.3 (4)	C19—C20—C21—C22	1.1 (4)
C8—N1—C9—C10	0.7 (4)	C20—C21—C22—C23	−0.5 (4)
N1—C9—C10—C6	−0.9 (4)	C21—C22—C23—C24	−0.3 (4)
C7—C6—C10—C9	0.7 (3)	C22—C23—C24—C19	0.4 (3)
C3—C6—C10—C9	−179.3 (2)	C22—C23—C24—C25	−177.6 (2)
C16—C11—C12—C13	−0.2 (3)	C20—C19—C24—C23	0.2 (3)
C11—C12—C13—C14	−0.9 (3)	C18—C19—C24—C23	−177.5 (2)
C11—C12—C13—C17	−179.8 (2)	C20—C19—C24—C25	178.1 (2)
C12—C13—C14—C15	0.4 (3)	C18—C19—C24—C25	0.4 (3)
C17—C13—C14—C15	179.3 (2)	C23—C24—C25—O4	30.4 (3)
C13—C14—C15—C16	1.2 (3)	C19—C24—C25—O4	−147.5 (2)
C12—C11—C16—C15	1.7 (3)	C23—C24—C25—O5	−150.7 (2)
C12—C11—C16—C18	−176.9 (2)	C19—C24—C25—O5	31.3 (3)
C14—C15—C16—C11	−2.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O4i	0.93	2.51	3.282 (3)	141
O5—H5···N2ii	0.82	1.84	2.641 (2)	166
O2—H2···N1iii	0.82	1.79	2.595 (2)	168
C1—H1···Cg1iv	0.93	2.54	3.449 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C19–C24 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O4i	0.93	2.51	3.282 (3)	141
O5—H5⋯N2ii	0.82	1.84	2.641 (2)	166
O2—H2⋯N1iii	0.82	1.79	2.595 (2)	168
C1—H1⋯Cg1iv	0.93	2.54	3.449 (3)	165

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