4-(2-Carboxy­benzo­yl)benzoic acid–4,4′-bipyridine (1/1)

Wang, J.-G.; Qin, J.-H.

doi:10.1107/S1600536808037823

4-(2-Carboxybenzoyl)benzoic acid–4,4′-bipyridine (1/1)

J.-G. Wang and J.-H. Qin

In the heteromolecular title compound, C₁₅H₁₀O₅·C₁₀H₈N₂, the two components are linked by O—H

N hydrogen bonds to form four-component ring supramolecular assemblies. These are further interconnected with neighbouring molecules by weak intermolecular C—H

π interactions and C—H

O hydrogen bonds to generate a three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808037823/si2130sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808037823/si2130Isup2.hkl Contains datablock I

CCDC reference: 712498

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C)= 0.003 Å
R factor = 0.045
wR factor = 0.128
Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Comment top

The asymmetric unit consists of one 4,4'-bipyridine molecule and one 4-(2-carboxylbenzoyl)benzoic acid molecule (Fig. 1). The two components are linked by O—H···N hydrogen bonds to form four-component ring supramolecular adducts (Tab. 1 & Fig. 2). The four-component ring supramolecular adducts interact with neigboring molecules via weak intermolecular C—H···π interactions and C—H···O hydrogen bonds (Tab. 1). The C—H···π interactions link the four-component ring supramolecular adducts into two-dimensional layers (Fig. 3), which are further connected by weak intermolecular C—H···O hydrogen bonds to generate a three-dimensional supramolecular structure (Fig. 4).

Related literature top

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 top

4,4'-bipyridine (0.1 mmol), 4-(2-carboxylbenzoyl)benzoic acid (0.1 mmol), and NaOH (0.2 mmol) were added to a H₂O solution (15 ml) in a Teflon-lined stainless steel reactor. The mixture was heated at 473 K for 3 d, and then slowly cooled down to room temperature. Colorless crystals of the title compound were obtained.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the heteromolecular components of the title compound with the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the four-component ring supramolecular adducts, formed by O—H···N hydrogen bonds.
	Fig. 3. A packing section of the title compound viewed down the a axis, indicating the C—H···π contacts by dashed lines.
	Fig. 4. A view of the molecular packing down the c axis.

4-(2-Carboxybenzoyl)benzoic acid–4,4'-bipyridine (1/1) top

Crystal data top

C₁₅H₁₀O₅·C₁₀H₈N₂	F(000) = 888
M_r = 426.41	D_x = 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 = 2.5–21.2°
b = 24.1886 (18) Å	µ = 0.10 mm⁻¹
c = 10.9560 (8) Å	T = 296 K
β = 95.873 (1)°	Block, colorless
V = 2026.8 (3) Å³	0.35 × 0.28 × 0.16 mm
Z = 4

Data collection top

Bruker CCD area detector diffractometer	3607 independent reflections
Radiation source: fine-focus sealed tube	2177 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −9→9
T_min = 0.957, T_max = 0.984	k = −28→28
10190 measured reflections	l = −13→7

Refinement top

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)] = 0.045	H-atom parameters constrained
wR(F²) = 0.128	w = 1/[σ²(F_o²) + (0.060P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3607 reflections	Δρ_max = 0.21 e Å⁻³
292 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	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)

Crystal data top

C₁₅H₁₀O₅·C₁₀H₈N₂	V = 2026.8 (3) Å³
M_r = 426.41	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.6883 (6) Å	µ = 0.10 mm⁻¹
b = 24.1886 (18) Å	T = 296 K
c = 10.9560 (8) Å	0.35 × 0.28 × 0.16 mm
β = 95.873 (1)°

Data collection top

Bruker CCD area detector diffractometer	3607 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2177 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.984	R_int = 0.041
10190 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.02	Δρ_max = 0.21 e Å⁻³
3607 reflections	Δρ_min = −0.17 e Å⁻³
292 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···Cg1^iv	0.93	2.54	3.449 (3)	165

Symmetry codes: (i) x+1, y, z+1; (ii) x−1, y, z; (iii) −x+1, −y, −z+2; (iv) x−1/2, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀O₅·C₁₀H₈N₂
M_r	426.41
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	7.6883 (6), 24.1886 (18), 10.9560 (8)
β (°)	95.873 (1)
V (Å³)	2026.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.35 × 0.28 × 0.16

Data collection
Diffractometer	Bruker CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.957, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	10190, 3607, 2177
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.128, 1.02
No. of reflections	3607
No. of parameters	292
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.17

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).