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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2399.
Published online 2008 November 20. doi:  10.1107/S1600536808037823
PMCID: PMC2959970

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

Abstract

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.

Related literature

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

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Object name is e-64-o2399-scheme1.jpg

Experimental

Crystal data

  • C15H10O5·C10H8N2
  • M r = 426.41
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2399-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

The authors thank Luoyang Normal University for supporting this work.

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

All hydrogen atoms were positioned geometrically and treated as riding, with C—H bond lengths constrained to 0.93 Å (aromatic CH) and O—H bond lengths constrained to 0.82 Å (OH), and with Uiso(H) = 1.2Ueq(C) and Uiso(H) = 1.5Ueq(O).

Figures

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.

Crystal data

C15H10O5·C10H8N2F000 = 888
Mr = 426.41Dx = 1.397 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P2ynCell parameters from 1385 reflections
a = 7.6883 (6) Åθ = 2.5–21.2º
b = 24.1886 (18) ŵ = 0.10 mm1
c = 10.9560 (8) ÅT = 296 (2) K
β = 95.8730 (10)ºBlock, colorless
V = 2026.8 (3) Å30.35 × 0.28 × 0.16 mm
Z = 4

Data collection

Bruker CCD area detector diffractometer3607 independent reflections
Radiation source: fine-focus sealed tube2177 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.041
T = 296(2) Kθmax = 25.1º
[var phi] and ω scansθmin = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 1997)h = −9→9
Tmin = 0.957, Tmax = 0.984k = −28→28
10190 measured reflectionsl = −13→7

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.02Δρmax = 0.21 e Å3
3607 reflectionsΔρmin = −0.17 e Å3
292 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0131 (14)
Secondary atom site location: difference Fourier map

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

xyzUiso*/Ueq
N10.7560 (3)0.00682 (8)0.99002 (17)0.0561 (5)
N20.9586 (2)0.15564 (8)0.46655 (17)0.0512 (5)
O10.2912 (3)−0.00260 (8)0.69911 (15)0.0779 (6)
O20.3035 (3)0.06365 (7)0.84053 (15)0.0671 (5)
H20.28370.03790.88590.101*
O30.5482 (2)0.25808 (7)0.42728 (14)0.0659 (5)
O40.0942 (2)0.13238 (8)0.19022 (17)0.0789 (6)
O50.1584 (2)0.20365 (7)0.31530 (14)0.0532 (4)
H50.08220.19080.35410.080*
C10.9364 (3)0.18081 (10)0.5716 (2)0.0557 (7)
H10.94930.21900.57540.067*
C20.8955 (3)0.15357 (10)0.6751 (2)0.0530 (6)
H2A0.88100.17330.74630.064*
C30.8761 (3)0.09687 (9)0.67290 (19)0.0426 (5)
C40.8951 (3)0.07078 (10)0.5629 (2)0.0521 (6)
H40.88040.03270.55600.062*
C50.9359 (3)0.10128 (11)0.4632 (2)0.0556 (6)
H5A0.94800.08280.39010.067*
C60.8351 (3)0.06565 (9)0.7835 (2)0.0436 (6)
C70.8857 (3)0.08447 (10)0.9015 (2)0.0515 (6)
H70.94770.11740.91340.062*
C80.8436 (3)0.05426 (11)1.0008 (2)0.0571 (7)
H80.87810.06771.07910.069*
C90.7071 (3)−0.01128 (10)0.8773 (2)0.0618 (7)
H90.6445−0.04420.86820.074*
C100.7445 (3)0.01621 (10)0.7733 (2)0.0561 (7)
H100.70890.00160.69620.067*
C110.4552 (3)0.11251 (9)0.44658 (19)0.0472 (6)
H110.48160.10160.36920.057*
C120.4068 (3)0.07337 (9)0.5287 (2)0.0503 (6)
H120.40060.03630.50600.060*
C130.3673 (3)0.08886 (9)0.64455 (19)0.0441 (6)
C140.3797 (3)0.14392 (10)0.6772 (2)0.0497 (6)
H140.35440.15480.75480.060*
C150.4293 (3)0.18291 (9)0.59573 (19)0.0481 (6)
H150.43920.21980.61940.058*
C160.4644 (3)0.16755 (9)0.47894 (19)0.0416 (5)
C170.3161 (3)0.04481 (11)0.7299 (2)0.0518 (6)
C180.5073 (3)0.21165 (10)0.3914 (2)0.0455 (6)
C190.5114 (3)0.19699 (9)0.25883 (18)0.0408 (5)
C200.6710 (3)0.20203 (9)0.2104 (2)0.0499 (6)
H200.76740.21580.25920.060*
C210.6878 (3)0.18689 (10)0.0910 (2)0.0561 (6)
H210.79570.18980.06020.067*
C220.5460 (3)0.16750 (10)0.0174 (2)0.0565 (7)
H220.55750.1576−0.06340.068*
C230.3861 (3)0.16268 (9)0.0633 (2)0.0499 (6)
H230.29020.14960.01290.060*
C240.3669 (3)0.17700 (9)0.18334 (19)0.0419 (5)
C250.1923 (3)0.16868 (10)0.2289 (2)0.0491 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0681 (14)0.0556 (14)0.0461 (12)0.0026 (11)0.0131 (10)0.0071 (10)
N20.0492 (12)0.0565 (14)0.0486 (12)−0.0050 (10)0.0086 (9)0.0031 (10)
O10.1202 (17)0.0535 (12)0.0602 (12)−0.0246 (11)0.0108 (10)0.0006 (10)
O20.1031 (15)0.0560 (11)0.0451 (10)−0.0019 (10)0.0217 (10)0.0098 (8)
O30.0921 (14)0.0547 (12)0.0515 (11)−0.0205 (10)0.0106 (9)−0.0029 (9)
O40.0604 (12)0.0931 (15)0.0854 (14)−0.0297 (11)0.0174 (10)−0.0236 (11)
O50.0504 (10)0.0576 (11)0.0538 (11)−0.0020 (8)0.0153 (8)0.0034 (8)
C10.0671 (17)0.0449 (15)0.0563 (17)−0.0067 (12)0.0129 (13)0.0014 (12)
C20.0642 (16)0.0476 (15)0.0489 (15)−0.0051 (12)0.0143 (12)−0.0005 (11)
C30.0406 (13)0.0469 (14)0.0412 (13)−0.0016 (10)0.0077 (10)0.0003 (11)
C40.0633 (16)0.0447 (14)0.0505 (15)−0.0066 (12)0.0167 (12)−0.0025 (11)
C50.0612 (16)0.0587 (17)0.0487 (15)−0.0053 (13)0.0149 (12)−0.0048 (12)
C60.0427 (13)0.0447 (14)0.0439 (13)0.0025 (10)0.0063 (10)0.0029 (11)
C70.0580 (15)0.0504 (15)0.0466 (15)−0.0050 (12)0.0083 (12)0.0004 (12)
C80.0671 (17)0.0623 (18)0.0425 (14)0.0015 (14)0.0075 (12)0.0006 (13)
C90.0805 (19)0.0502 (16)0.0550 (16)−0.0103 (13)0.0090 (14)0.0087 (13)
C100.0767 (18)0.0499 (16)0.0413 (14)−0.0090 (13)0.0050 (12)0.0010 (11)
C110.0587 (15)0.0484 (15)0.0351 (12)0.0046 (12)0.0070 (11)−0.0012 (11)
C120.0643 (16)0.0406 (14)0.0457 (14)0.0020 (11)0.0039 (12)0.0001 (11)
C130.0472 (14)0.0500 (15)0.0347 (13)0.0023 (11)0.0018 (10)0.0037 (11)
C140.0601 (15)0.0511 (15)0.0387 (13)0.0014 (12)0.0092 (11)−0.0031 (11)
C150.0606 (15)0.0421 (14)0.0421 (14)−0.0018 (11)0.0068 (11)0.0010 (11)
C160.0427 (13)0.0462 (14)0.0360 (12)0.0002 (10)0.0044 (10)0.0022 (10)
C170.0573 (16)0.0556 (17)0.0418 (15)−0.0004 (13)0.0019 (12)0.0065 (12)
C180.0449 (14)0.0508 (16)0.0409 (13)−0.0018 (11)0.0054 (10)0.0017 (11)
C190.0438 (13)0.0427 (13)0.0365 (12)−0.0013 (10)0.0067 (10)0.0052 (10)
C200.0435 (14)0.0578 (16)0.0485 (14)−0.0035 (11)0.0052 (11)0.0032 (12)
C210.0468 (15)0.0667 (17)0.0566 (16)0.0037 (12)0.0144 (12)0.0023 (13)
C220.0624 (17)0.0642 (17)0.0448 (14)0.0070 (13)0.0150 (13)−0.0036 (12)
C230.0516 (15)0.0510 (15)0.0461 (14)−0.0025 (11)0.0012 (11)−0.0041 (11)
C240.0458 (14)0.0396 (13)0.0408 (13)0.0003 (10)0.0064 (11)0.0046 (10)
C250.0494 (15)0.0539 (16)0.0439 (14)−0.0026 (12)0.0041 (11)0.0024 (12)

Geometric parameters (Å, °)

N1—C91.328 (3)C9—H90.9300
N1—C81.330 (3)C10—H100.9300
N2—C51.327 (3)C11—C161.378 (3)
N2—C11.328 (3)C11—C121.383 (3)
O1—C171.205 (3)C11—H110.9300
O2—C171.308 (3)C12—C131.387 (3)
O2—H20.8200C12—H120.9300
O3—C181.220 (3)C13—C141.380 (3)
O4—C251.205 (3)C13—C171.497 (3)
O5—C251.315 (3)C14—C151.379 (3)
O5—H50.8200C14—H140.9300
C1—C21.376 (3)C15—C161.385 (3)
C1—H10.9300C15—H150.9300
C2—C31.379 (3)C16—C181.493 (3)
C2—H2A0.9300C18—C191.499 (3)
C3—C41.382 (3)C19—C201.391 (3)
C3—C61.489 (3)C19—C241.402 (3)
C4—C51.380 (3)C20—C211.377 (3)
C4—H40.9300C20—H200.9300
C5—H5A0.9300C21—C221.371 (3)
C6—C101.383 (3)C21—H210.9300
C6—C71.388 (3)C22—C231.380 (3)
C7—C81.376 (3)C22—H220.9300
C7—H70.9300C23—C241.383 (3)
C8—H80.9300C23—H230.9300
C9—C101.375 (3)C24—C251.493 (3)
C9—N1—C8117.3 (2)C14—C13—C12118.8 (2)
C5—N2—C1116.7 (2)C14—C13—C17122.7 (2)
C17—O2—H2109.5C12—C13—C17118.4 (2)
C25—O5—H5109.5C15—C14—C13120.6 (2)
N2—C1—C2123.7 (2)C15—C14—H14119.7
N2—C1—H1118.1C13—C14—H14119.7
C2—C1—H1118.1C14—C15—C16120.5 (2)
C1—C2—C3119.7 (2)C14—C15—H15119.8
C1—C2—H2A120.2C16—C15—H15119.8
C3—C2—H2A120.2C11—C16—C15119.2 (2)
C2—C3—C4116.7 (2)C11—C16—C18122.3 (2)
C2—C3—C6121.4 (2)C15—C16—C18118.6 (2)
C4—C3—C6121.9 (2)O1—C17—O2124.5 (2)
C5—C4—C3119.9 (2)O1—C17—C13123.2 (2)
C5—C4—H4120.0O2—C17—C13112.3 (2)
C3—C4—H4120.0O3—C18—C16121.2 (2)
N2—C5—C4123.2 (2)O3—C18—C19119.9 (2)
N2—C5—H5A118.4C16—C18—C19118.8 (2)
C4—C5—H5A118.4C20—C19—C24118.8 (2)
C10—C6—C7116.7 (2)C20—C19—C18117.1 (2)
C10—C6—C3121.3 (2)C24—C19—C18124.02 (18)
C7—C6—C3122.0 (2)C21—C20—C19120.7 (2)
C8—C7—C6119.7 (2)C21—C20—H20119.6
C8—C7—H7120.1C19—C20—H20119.6
C6—C7—H7120.1C22—C21—C20120.2 (2)
N1—C8—C7123.1 (2)C22—C21—H21119.9
N1—C8—H8118.4C20—C21—H21119.9
C7—C8—H8118.4C21—C22—C23120.0 (2)
N1—C9—C10123.3 (2)C21—C22—H22120.0
N1—C9—H9118.4C23—C22—H22120.0
C10—C9—H9118.4C22—C23—C24120.7 (2)
C9—C10—C6119.8 (2)C22—C23—H23119.6
C9—C10—H10120.1C24—C23—H23119.6
C6—C10—H10120.1C23—C24—C19119.49 (19)
C16—C11—C12120.3 (2)C23—C24—C25118.1 (2)
C16—C11—H11119.9C19—C24—C25122.33 (19)
C12—C11—H11119.9O4—C25—O5124.0 (2)
C11—C12—C13120.6 (2)O4—C25—C24122.1 (2)
C11—C12—H12119.7O5—C25—C24113.9 (2)
C13—C12—H12119.7
C5—N2—C1—C21.3 (3)C14—C15—C16—C18176.4 (2)
N2—C1—C2—C30.2 (4)C14—C13—C17—O1173.8 (2)
C1—C2—C3—C4−1.7 (3)C12—C13—C17—O1−7.4 (3)
C1—C2—C3—C6178.9 (2)C14—C13—C17—O2−6.8 (3)
C2—C3—C4—C51.6 (3)C12—C13—C17—O2172.1 (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—O315.8 (3)
C3—C4—C5—N20.0 (4)C11—C16—C18—C1910.3 (3)
C2—C3—C6—C10151.9 (2)C15—C16—C18—C19−168.35 (19)
C4—C3—C6—C10−27.6 (3)O3—C18—C19—C2059.3 (3)
C2—C3—C6—C7−28.2 (3)C16—C18—C19—C20−116.6 (2)
C4—C3—C6—C7152.4 (2)O3—C18—C19—C24−123.0 (2)
C10—C6—C7—C8−0.5 (3)C16—C18—C19—C2461.1 (3)
C3—C6—C7—C8179.6 (2)C24—C19—C20—C21−0.9 (3)
C9—N1—C8—C7−0.4 (4)C18—C19—C20—C21176.9 (2)
C6—C7—C8—N10.3 (4)C19—C20—C21—C221.1 (4)
C8—N1—C9—C100.7 (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—C90.7 (3)C22—C23—C24—C190.4 (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—C230.2 (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—C25178.1 (2)
C12—C13—C14—C150.4 (3)C18—C19—C24—C250.4 (3)
C17—C13—C14—C15179.3 (2)C23—C24—C25—O430.4 (3)
C13—C14—C15—C161.2 (3)C19—C24—C25—O4−147.5 (2)
C12—C11—C16—C151.7 (3)C23—C24—C25—O5−150.7 (2)
C12—C11—C16—C18−176.9 (2)C19—C24—C25—O531.3 (3)
C14—C15—C16—C11−2.2 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C8—H8···O4i0.932.513.282 (3)141
O5—H5···N2ii0.821.842.641 (2)166
O2—H2···N1iii0.821.792.595 (2)168
C1—H1···Cg1iv0.932.543.449 (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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2130).

References

  • Bhogala, B. R., Basavoju, S. & Nangia, A. (2005). Cryst. Growth Des.5, 1683–1686.
  • Bruker (1997). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Fun, H.-K. & Kia, R. (2008). Acta Cryst. E64, m1116–m1117. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, Y.-T., Tang, G.-M., Zhang, Y.-C. & Wan, W.-Z. (2008). Acta Cryst. E64, o1753. [PMC free article] [PubMed]

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