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Logo of actae2this articlesearchopen accesssubmitActa Crystallographica Section E: Crystallographic CommunicationsActa Crystallographica Section E: Crystallographic Communications
 
Acta Crystallogr E Crystallogr Commun. 2017 July 1; 73(Pt 8): 1192–1196.
Published online 2017 July 17. doi:  10.1107/S2056989017010167
PMCID: PMC5598847

Crystal structures of 4-meth­oxy­benzoic acid–1,3-bis­(pyridin-4-yl)propane (2/1) and biphenyl-4,4′-di­carb­oxy­lic acid–4-meth­oxy­pyridine (1/2)

Abstract

The crystal structures of two hydrogen-bonded compounds, namely 4-meth­oxy­benzoic acid–1,3-bis­(pyridin-4-yl)propane (2/1), C13H14.59N2·C8H7.67O3·C8H7.74O3, (I), and biphenyl-4,4′-di­carb­oxy­lic acid–4-meth­oxy­pyridine (1/2), C14H9.43O4·C6H7.32NO·C6H7.25NO, (II), have been determined at 93 K. In (I), the asymmetric unit consists of two crystallographically independent 4-meth­oxy­benzoic acid mol­ecules and one 1,3-bis­(pyridin-4-yl)propane mol­ecule. The asymmetric unit of (II) comprises one biphenyl-4,4′-di­carb­oxy­lic acid mol­ecule and two independent 4-meth­oxy­pyridine mol­ecules. In each crystal, the acid and base mol­ecules are linked by short O—H(...)N/N—H(...)O hydrogen bonds, in which H atoms are disordered over the acid O-atom and base N-atom sites, forming a linear hydrogen-bonded 2:1 or 1:2 unit of the acid and the base. The 2:1 units of (I) are linked via C—H(...)π, π–π and C—H(...)O inter­actions into a tape structure along [101], while the 1:2 units of (II) form a double-chain structure along [-101] through π–π and C—H(...)O inter­actions.

Keywords: crystal structure, 4-meth­oxy­benzoic acid, 1,3-bis­(pyridin-4-yl)propane, biphenyl-4,4′-di­carb­oxy­lic acid, 4-meth­oxy­pyridine

Chemical context  

Co-crystals of the 4-alk­oxy­benzoic acid–4,4′-bipyridyl (2/1) and 4-alk­oxy­benzoic acid–(E)-1,2-bis­(pyridin-4-yl)ethene (2/1) systems show thermotropic liquid crystallinity (Kato et al., 1990  , 1993  ; Grunert et al., 1997  ). Of these co-crystals, the crystal structures of 4,4′-bipyridyl with 4-meth­oxy­benzoic acid (Mukherjee & Desiraju, 2014  ; Ramon et al., 2014  ), 4-eth­oxy, 4-(n-prop­oxy)- and 4-(n-but­oxy)benzoic acid (Tabuchi et al., 2015a  ), and the crystal structures of (E)-1,2-bis­(pyridin-4-yl)ethene with 4-meth­oxy-, 4-eth­oxy-, 4-(n-prop­oxy)-, 4-(n-but­oxy)-, 4-(n-pent­yloxy)- and 4-(n-hex­yloxy)benzoic acid (Tabuchi et al., 2016a  ,b  ) have been reported. In these crystals, the two acids and the base are held together by short inter­molecular O—H(...)N hydrogen bonds, forming linear 2:1 units of the acid and the base. As an expansion of our work on the structural characterization of hydrogen-bonded co-crystals with organic acid and base mol­ecules, we have prepared 4-meth­oxy­benzoic acid–1,3-bis­(pyridin-4-yl)propane (2/1), (I), and biphenyl-4,4′-di­carb­oxy­lic acid–4-meth­oxy­pyridine (1/2), (II), and analyzed the crystal structures.

Structural commentary  

The mol­ecular structures of (I) and (II) are shown in Figs. 1  and 2  , respectively. The asymmetric unit of (I) consists of two crystallographically independent 4-meth­oxy­benzoic acid mol­ecules and one 1,3-bis­(pyridin-4-yl)propane mol­ecule. The acid and base mol­ecules are held together via short O—H(...)N/N—H(...)O hydrogen bonds between the carboxyl O and pyridine N atoms (Table 1  ), forming a 2:1 unit. In the hydrogen bonds, the H atoms are disordered over O- and N-atom sites, with occupancy ratios of 0.67 (3):0.33 (3) between atoms O1 and N1, and 0.74 (3):0.26 (3) between atoms O4 and N2. The O1/C7/O2 and N1/C17–C21 planes in one hydrogen-bonded unit are approximately perpendicular to each other, with a dihedral angle of 85.97 (13)°. On the other hand, the O4/C15/O5 and N2/C22–C26 planes in the other hydrogen-bonded unit are approximately planar, with a dihedral angle of 10.18 (14)°, and a weak C—H(...)O hydrogen bond (C26—H26(...)O5) is observed in the hydrogen-bonded unit. The dihedral angles between the pyridine N1/C17–C21 and N2/C22–C26 rings, between the benzene C1–C6 and pyridine N1/C17–C21 planes, and between the benzene C9–C14 and pyridine N2/C22–C26 planes are 8.68 (6), 72.93 (6) and 9.05 (6)°, respectively.

An external file that holds a picture, illustration, etc.
Object name is e-73-01192-scheme1.jpg

Figure 1
The mol­ecular structure of compound (I), showing the atom-numbering scheme. Displacement ellipsoids of non-H atoms are drawn at the 50% probability level and H atoms are drawn as circles of arbitrary size.
Figure 2
The mol­ecular structure of compound (II), showing the atom-numbering scheme. Displacement ellipsoids of non-H atoms are drawn at the 50% probability level and H atoms are drawn as circles of arbitrary size.
Table 1
Hydrogen-bond geometry (Å, °) for (I)

The asymmetric unit of (II) is composed of one biphenyl-4,4′-di­carb­oxy­lic acid mol­ecule and two crystallographically independent 4-meth­oxy­pyridine mol­ecules, and the acid and the two bases are held together by short O—H(...)N/N—H(...)O hydrogen bonds (Table 2  ), forming a linear 1:2 aggregate with pseudo-inversion symmetry. Similar to compound (I), the H atoms in the hydrogen bonds are disordered over two sites, with occupancy ratios of 0.68 (3):0.32 (3) between atoms O1 and N1, and 0.75 (3):0.25 (3) between atoms O3 and N2. The hydrogen-bonded 1:2 unit is approximately planar and weak C—H(...)O hydrogen bonds (C19—H19(...)O2 and C25—H25(...)O4) are observed. The dihedral angle between the benzene rings of the biphenyl-4,4′-di­carb­oxy­lic acid is 3.87 (5)°. The N1/C15–C19 pyridine ring makes dihedral angles of 5.62 (12) and 2.55 (5)°, respectively, with the O1/C7/O2 and C1–C6 planes. The N2/C21–C25 pyridine ring makes dihedral angles of 6.84 (12) and 9.50 (5)°, respectively, with the O3/C14/O4 and C8–C13 planes.

Table 2
Hydrogen-bond geometry (Å, °) for (II)

Supra­molecular features  

In the crystal of (I), the 2:1 units are linked by a pair of C—H(...)π inter­actions (C5—H5(...)Cg2v; Cg2 in the centroid of the pyridine N2/C22–C26 ring; symmetry code as given in Table 1  ), and a π–π inter­action [Cg1(...)Cg1v = 3.6588 (16) Å; Cg1 is the centroid of the pyridine N1/C17–C21 ring], forming an inversion dimer. The dimers are linked via C—H(...)O inter­actions (C17—H17(...)O6i; Table 1  ) into a tape structure running along [101] (Fig. 3  ). The tapes running along the same direction are further linked via the rest of the C—H(...)O and C—H(...)π inter­actions (Table 1  ), forming a three-dimensional network (Fig. 4  ).

Figure 3
A partial packing diagram of compound (I), showing inversion dimers formed by C—H(...)π inter­actions (orange–red dashed lines) and π–π stacking inter­actions (brown dashed lines), and ...
Figure 4
A packing diagram of compound (I), viewed approximately along [101], showing C—H(...)O hydrogen bonds (black dashed lines). C—H(...)π inter­actions (orange–red dashed lines) and π–π ...

In the crystal of (II), the 1:2 units are linked by a C—H(...)O inter­action (C20—H20A(...)O6ii; symmetry code as given in Table 2  ) into a chain structure along [An external file that holds a picture, illustration, etc.
Object name is e-73-01192-efi1.jpg01]. Ajacent chains, which are related by an inversion centre, are further linked via π–π inter­actions between pyridine N2/C21–C25 rings [centroid-centroid distance = 3.8113 (13) Å] and between the benzene C1–C6 and pyridine N1/C15–C19 rings [centroid-centroid distance = 3.6613 (12) Å], forming a double-chain structure (Fig. 5  ). Weak C—H(...)O and C—H(...)π inter­actions are observed between the double chains (Table 2  ) and the 1:2 units are arranged in the crystals with their long axes parallel to each other (Fig. 6  ).

Figure 5
A partial packing diagram of compound (II), showing a double-chain structure formed by O—H(...)N/N—H(...)O hydrogen bonds, C—H(...)O inter­actions (black dashed lines) and π–π stacking ...
Figure 6
A partial packing diagram of compound (II), viewed along [An external file that holds a picture, illustration, etc.
Object name is e-73-01192-efi1.jpg01], showing the arrangement of the mol­ecular chains. C—H(...)O hydrogen bonds, C—H(...)π inter­actions and π–π stacking ...

Database survey  

The crystal structures of co-crystals similar to compound (I), namely 4-meth­oxy­benzoic acid–1,2-bis­(pyridin-4-yl)ethane (2/1) (Mukherjee & Desiraju, 2014  ), 4-eth­oxy­benzoic acid–1,2-bis­(pyridin-4-yl)ethane (2/1), 4-(n-prop­oxy)benzoic acid–bis­(pyridin-4-yl)ethane (2/1) and 4-(n-but­oxy)benzoic acid–1,2-bis­(pyridin-4-yl)ethane (2/1) (Tabuchi et al., 2015b  ) have been reported. These compounds also show thermotropic liquid crystallinity (Tabuchi et al., 2015b  ). A search of the Cambridge Structural Database (CSD, Version 5.38, last update February 2017; Groom et al., 2016  ) for organic co-crystals or salts similar to compound (II), namely 4,4′-bi­phenyldi­carb­oxy­lic acid with pyridine derivatives, gave three structures, with CSD refcodes ATOJEZ (Gong et al., 2011  ), BIKFUX (Cruz et al., 2004  ) and MAZYUI (Du et al., 2006  ).

Synthesis and crystallization  

Single crystals of compound (I) were obtained by slow evaporation from an ethanol solution (200 ml) of 1,3-bis­(pyridin-4-yl)propane (100 mg) with 4-meth­oxy­benzoic acid (155 mg) at room temperature. Crystals of compound (I) were obtained by slow evaporation from a 4-meth­oxy­pyridine solution (5 ml) of bi­phenyl-4,4′-di­carb­oxy­lic acid (100 mg) at room temperature.

Refinement  

Crystal data, data collection and structure refinement details are summarized in Table 3  . All H atoms in compounds (I) and (II) were found in difference Fourier maps. The H atoms in both compounds which are involved in the O—H(...)N/N—H(...)O hydrogen bonds were found to be disordered over two positions in difference Fourier maps. The positional parameters and the occupancy factors were refined with bond-length restraints of O—H = 0.84 (2) Å and N—H = 0.88 (2) Å, and with U iso(H) = 1.5U eq(O,N). Other H atoms were positioned geometrically (C—H = 0.95–0.99 Å) and were treated as riding, with U iso(H) = 1.2U eq(C) or 1.5U eq(methyl C). For compound (I), six reflections were omitted in the final refinement owing to poor agreement between the measured and calculated intensities.

Table 3
Experimental details

Supplementary Material

Crystal structure: contains datablock(s) I, II, General. DOI: 10.1107/S2056989017010167/lh5847sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989017010167/lh5847Isup2.hkl

Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989017010167/lh5847IIsup3.hkl

CCDC references: 1560979, 1560978

Additional supporting information: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

4-Methoxybenzoic acid–1,3-bis(pyridin-4-yl)propane (2/1) (I)   Crystal data

C13H14.59N2·C8H7.67O3·C8H7.74O3Z = 2
Mr = 502.55F(000) = 532.00
Triclinic, P1Dx = 1.347 Mg m3
a = 7.759 (3) ÅMo Kα radiation, λ = 0.71075 Å
b = 8.733 (4) ÅCell parameters from 13611 reflections
c = 19.904 (7) Åθ = 3.0–30.1°
α = 91.087 (16)°µ = 0.10 mm1
β = 90.593 (17)°T = 93 K
γ = 113.241 (15)°Platelet, colorless
V = 1238.7 (8) Å30.54 × 0.50 × 0.19 mm

4-Methoxybenzoic acid–1,3-bis(pyridin-4-yl)propane (2/1) (I)   Data collection

Rigaku R-AXIS RAPID II diffractometer4561 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm-1Rint = 0.033
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: numerical (NUMABS; Higashi, 1999)h = −10→10
Tmin = 0.970, Tmax = 0.982k = −11→11
12378 measured reflectionsl = −25→25
5653 independent reflections

4-Methoxybenzoic acid–1,3-bis(pyridin-4-yl)propane (2/1) (I)   Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: mixed
wR(F2) = 0.106H atoms treated by a mixture of independent and constrained refinement
S = 1.07w = 1/[σ2(Fo2) + (0.0644P)2] where P = (Fo2 + 2Fc2)/3
5653 reflections(Δ/σ)max = 0.001
350 parametersΔρmax = 0.27 e Å3
4 restraintsΔρmin = −0.30 e Å3

4-Methoxybenzoic acid–1,3-bis(pyridin-4-yl)propane (2/1) (I)   Special details

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. Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences.

4-Methoxybenzoic acid–1,3-bis(pyridin-4-yl)propane (2/1) (I)   Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
O10.13329 (12)0.23348 (10)0.63470 (4)0.02284 (19)
H1A0.132 (4)0.258 (3)0.5927 (8)0.034*0.67 (3)
O20.29365 (12)0.08921 (10)0.59389 (4)0.0251 (2)
O30.39277 (11)0.01871 (10)0.90676 (4)0.02030 (18)
O4−0.32465 (11)0.58373 (10)−0.08794 (4)0.02144 (18)
H4A−0.280 (3)0.580 (3)−0.0475 (8)0.032*0.74 (3)
O5−0.10967 (13)0.84664 (10)−0.08750 (4)0.0271 (2)
O6−0.44746 (12)0.77002 (10)−0.38406 (4)0.02324 (19)
N10.12203 (14)0.33437 (12)0.51474 (5)0.0211 (2)
H1B0.126 (7)0.290 (5)0.5542 (14)0.032*0.33 (3)
N2−0.15522 (13)0.57544 (12)0.02868 (5)0.0190 (2)
H4B−0.208 (7)0.577 (7)−0.0101 (16)0.028*0.26 (3)
C10.27123 (14)0.11283 (13)0.71215 (5)0.0159 (2)
C20.34417 (15)−0.00596 (13)0.72592 (5)0.0181 (2)
H20.3669 (19)−0.0701 (16)0.6893 (7)0.020 (3)*
C30.38150 (15)−0.03646 (13)0.79103 (6)0.0185 (2)
H30.429441−0.1189890.7996980.022*
C40.34844 (14)0.05478 (13)0.84434 (5)0.0159 (2)
C50.27662 (14)0.17456 (13)0.83148 (5)0.0163 (2)
H50.2547840.2372970.8674500.020*
C60.23720 (14)0.20155 (12)0.76565 (5)0.0157 (2)
H60.1861150.2819240.7569370.019*
C70.23409 (15)0.14359 (13)0.64133 (5)0.0176 (2)
C80.35498 (18)0.10742 (15)0.96211 (5)0.0244 (3)
H8A0.4285960.2271920.9578340.037*
H8B0.3894430.0698841.0043410.037*
H8C0.2210740.0858510.9620130.037*
C9−0.29525 (14)0.73995 (13)−0.18604 (5)0.0159 (2)
C10−0.19209 (15)0.88110 (13)−0.22204 (5)0.0175 (2)
H10−0.0888270.968468−0.2007110.021*
C11−0.23745 (15)0.89642 (13)−0.28853 (5)0.0180 (2)
H11−0.1655310.992937−0.3126750.022*
C12−0.38967 (15)0.76852 (13)−0.31932 (5)0.0174 (2)
C13−0.49534 (15)0.62658 (13)−0.28356 (5)0.0184 (2)
H13−0.5998120.539892−0.3046220.022*
C14−0.44744 (15)0.61277 (13)−0.21759 (5)0.0173 (2)
H14−0.5187060.515903−0.1935210.021*
C15−0.23371 (15)0.73027 (13)−0.11581 (5)0.0172 (2)
C16−0.34828 (18)0.91561 (15)−0.42219 (6)0.0263 (3)
H16A−0.3650211.011781−0.4018500.039*
H16B−0.3976330.897616−0.4684880.039*
H16C−0.2144670.936813−0.4222420.039*
C170.26553 (17)0.48170 (15)0.50821 (6)0.0252 (3)
H170.3477760.5281360.5456920.030*
C180.29914 (17)0.56891 (15)0.44953 (6)0.0238 (3)
H180.4031640.6728650.4469640.029*
C190.18023 (15)0.50428 (13)0.39398 (5)0.0168 (2)
C200.03222 (17)0.35114 (14)0.40097 (6)0.0226 (2)
H20−0.0521700.3015470.3643260.027*
C210.00822 (17)0.27103 (14)0.46161 (6)0.0241 (3)
H21−0.0938650.1662850.4655570.029*
C22−0.20434 (16)0.45762 (14)0.07493 (5)0.0203 (2)
H22−0.3140480.3593570.0668000.024*
C23−0.10326 (16)0.47160 (13)0.13413 (5)0.0193 (2)
H23−0.1435130.3842250.1654540.023*
C240.05757 (15)0.61441 (13)0.14743 (5)0.0165 (2)
C250.11057 (15)0.73538 (13)0.09840 (5)0.0189 (2)
H250.2209690.8339440.1047890.023*
C260.00299 (16)0.71201 (14)0.04075 (5)0.0198 (2)
H260.0420300.7959850.0079560.024*
C270.21952 (16)0.60443 (13)0.33100 (5)0.0203 (2)
H27A0.3502220.6275640.3181570.024*
H27B0.2133360.7130500.3422220.024*
C280.09391 (15)0.53060 (13)0.26962 (5)0.0171 (2)
H28A−0.0352740.5208280.2785370.021*
H28B0.0895350.4180130.2587520.021*
C290.17452 (15)0.64592 (13)0.21094 (5)0.0188 (2)
H29A0.2020960.7614470.2268540.023*
H29B0.2957210.6403330.1993590.023*

4-Methoxybenzoic acid–1,3-bis(pyridin-4-yl)propane (2/1) (I)   Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0278 (4)0.0288 (4)0.0157 (4)0.0149 (3)0.0010 (3)0.0051 (3)
O20.0313 (4)0.0287 (4)0.0168 (4)0.0133 (4)0.0017 (3)−0.0015 (3)
O30.0236 (4)0.0241 (4)0.0163 (4)0.0128 (3)−0.0020 (3)0.0023 (3)
O40.0218 (4)0.0214 (4)0.0188 (4)0.0059 (3)−0.0023 (3)0.0059 (3)
O50.0331 (5)0.0214 (4)0.0199 (4)0.0034 (4)−0.0091 (4)0.0014 (3)
O60.0308 (4)0.0205 (4)0.0151 (4)0.0068 (3)−0.0054 (3)0.0003 (3)
N10.0261 (5)0.0240 (5)0.0157 (4)0.0126 (4)−0.0012 (4)0.0013 (4)
N20.0197 (4)0.0230 (5)0.0156 (4)0.0100 (4)−0.0013 (4)0.0008 (4)
C10.0125 (4)0.0152 (5)0.0169 (5)0.0021 (4)−0.0002 (4)0.0011 (4)
C20.0172 (5)0.0170 (5)0.0186 (5)0.0053 (4)0.0014 (4)−0.0009 (4)
C30.0176 (5)0.0170 (5)0.0228 (5)0.0087 (4)0.0004 (4)0.0023 (4)
C40.0129 (4)0.0168 (5)0.0158 (5)0.0033 (4)−0.0004 (4)0.0027 (4)
C50.0162 (5)0.0158 (5)0.0161 (5)0.0053 (4)0.0010 (4)0.0001 (4)
C60.0148 (5)0.0137 (5)0.0178 (5)0.0046 (4)0.0009 (4)0.0027 (4)
C70.0161 (5)0.0158 (5)0.0171 (5)0.0023 (4)0.0012 (4)0.0016 (4)
C80.0321 (6)0.0304 (6)0.0151 (5)0.0169 (5)−0.0011 (5)0.0019 (4)
C90.0165 (5)0.0168 (5)0.0155 (5)0.0077 (4)0.0002 (4)0.0004 (4)
C100.0166 (5)0.0161 (5)0.0182 (5)0.0047 (4)−0.0005 (4)0.0003 (4)
C110.0182 (5)0.0172 (5)0.0175 (5)0.0057 (4)0.0018 (4)0.0023 (4)
C120.0215 (5)0.0197 (5)0.0140 (5)0.0113 (4)−0.0013 (4)−0.0010 (4)
C130.0184 (5)0.0158 (5)0.0192 (5)0.0050 (4)−0.0034 (4)−0.0025 (4)
C140.0168 (5)0.0154 (5)0.0196 (5)0.0062 (4)0.0006 (4)0.0015 (4)
C150.0182 (5)0.0185 (5)0.0166 (5)0.0090 (4)0.0004 (4)0.0013 (4)
C160.0360 (7)0.0253 (6)0.0153 (5)0.0095 (5)−0.0002 (5)0.0034 (4)
C170.0271 (6)0.0292 (6)0.0171 (5)0.0092 (5)−0.0063 (5)−0.0007 (5)
C180.0238 (6)0.0237 (6)0.0190 (5)0.0042 (5)−0.0049 (5)−0.0003 (4)
C190.0195 (5)0.0188 (5)0.0149 (5)0.0108 (4)−0.0011 (4)−0.0003 (4)
C200.0242 (6)0.0236 (6)0.0166 (5)0.0061 (5)−0.0047 (4)0.0002 (4)
C210.0265 (6)0.0219 (5)0.0198 (5)0.0052 (5)−0.0009 (5)0.0025 (4)
C220.0190 (5)0.0217 (5)0.0192 (5)0.0071 (4)−0.0004 (4)0.0013 (4)
C230.0203 (5)0.0192 (5)0.0179 (5)0.0072 (4)0.0016 (4)0.0038 (4)
C240.0173 (5)0.0206 (5)0.0147 (5)0.0109 (4)0.0008 (4)0.0015 (4)
C250.0175 (5)0.0194 (5)0.0190 (5)0.0063 (4)−0.0002 (4)0.0026 (4)
C260.0209 (5)0.0216 (5)0.0175 (5)0.0088 (4)0.0017 (4)0.0043 (4)
C270.0238 (5)0.0185 (5)0.0165 (5)0.0061 (4)−0.0032 (4)0.0020 (4)
C280.0174 (5)0.0182 (5)0.0166 (5)0.0078 (4)−0.0015 (4)0.0014 (4)
C290.0188 (5)0.0195 (5)0.0168 (5)0.0062 (4)−0.0027 (4)0.0025 (4)

4-Methoxybenzoic acid–1,3-bis(pyridin-4-yl)propane (2/1) (I)   Geometric parameters (Å, º)

O1—C71.3158 (15)C11—C121.3914 (16)
O1—H1A0.869 (17)C11—H110.9500
O2—C71.2229 (13)C12—C131.3995 (15)
O3—C41.3610 (14)C13—C141.3814 (16)
O3—C81.4330 (13)C13—H130.9500
O4—C151.3289 (13)C14—H140.9500
O4—H4A0.879 (16)C16—H16A0.9800
O5—C151.2132 (14)C16—H16B0.9800
O6—C121.3620 (14)C16—H16C0.9800
O6—C161.4356 (14)C17—C181.3769 (17)
N1—C211.3330 (16)C17—H170.9500
N1—C171.3382 (16)C18—C191.3915 (16)
N1—H1B0.889 (19)C18—H180.9500
N2—C221.3360 (15)C19—C201.3874 (16)
N2—C261.3470 (15)C19—C271.5061 (15)
N2—H4B0.87 (2)C20—C211.3838 (17)
C1—C61.3928 (14)C20—H200.9500
C1—C21.3938 (17)C21—H210.9500
C1—C71.4864 (16)C22—C231.3850 (17)
C2—C31.3786 (16)C22—H220.9500
C2—H20.971 (13)C23—C241.3910 (16)
C3—C41.4005 (15)C23—H230.9500
C3—H30.9500C24—C251.3936 (15)
C4—C51.3919 (16)C24—C291.5043 (16)
C5—C61.3878 (15)C25—C261.3755 (17)
C5—H50.9500C25—H250.9500
C6—H60.9500C26—H260.9500
C8—H8A0.9800C27—C281.5190 (16)
C8—H8B0.9800C27—H27A0.9900
C8—H8C0.9800C27—H27B0.9900
C9—C101.3930 (14)C28—C291.5271 (15)
C9—C141.3947 (16)C28—H28A0.9900
C9—C151.4871 (16)C28—H28B0.9900
C10—C111.3882 (16)C29—H29A0.9900
C10—H100.9500C29—H29B0.9900
C7—O1—H1A108.6 (17)O5—C15—C9122.12 (10)
C4—O3—C8116.51 (9)O4—C15—C9114.09 (9)
C15—O4—H4A111.9 (14)O6—C16—H16A109.5
C12—O6—C16117.68 (9)O6—C16—H16B109.5
C21—N1—C17117.75 (10)H16A—C16—H16B109.5
C21—N1—H1B130 (3)O6—C16—H16C109.5
C17—N1—H1B112 (3)H16A—C16—H16C109.5
C22—N2—C26117.21 (10)H16B—C16—H16C109.5
C22—N2—H4B130 (4)N1—C17—C18122.84 (11)
C26—N2—H4B113 (4)N1—C17—H17118.6
C6—C1—C2118.66 (10)C18—C17—H17118.6
C6—C1—C7121.65 (10)C17—C18—C19119.78 (11)
C2—C1—C7119.69 (9)C17—C18—H18120.1
C3—C2—C1121.08 (10)C19—C18—H18120.1
C3—C2—H2119.2 (9)C20—C19—C18117.10 (10)
C1—C2—H2119.7 (9)C20—C19—C27124.59 (10)
C2—C3—C4119.70 (11)C18—C19—C27118.31 (10)
C2—C3—H3120.1C21—C20—C19119.63 (11)
C4—C3—H3120.1C21—C20—H20120.2
O3—C4—C5124.33 (9)C19—C20—H20120.2
O3—C4—C3115.68 (10)N1—C21—C20122.90 (11)
C5—C4—C3119.98 (10)N1—C21—H21118.6
C6—C5—C4119.44 (10)C20—C21—H21118.6
C6—C5—H5120.3N2—C22—C23123.27 (11)
C4—C5—H5120.3N2—C22—H22118.4
C5—C6—C1121.13 (10)C23—C22—H22118.4
C5—C6—H6119.4C22—C23—C24119.58 (11)
C1—C6—H6119.4C22—C23—H23120.2
O2—C7—O1123.73 (11)C24—C23—H23120.2
O2—C7—C1122.00 (11)C23—C24—C25116.96 (11)
O1—C7—C1114.28 (9)C23—C24—C29124.26 (10)
O3—C8—H8A109.5C25—C24—C29118.78 (10)
O3—C8—H8B109.5C26—C25—C24119.98 (10)
H8A—C8—H8B109.5C26—C25—H25120.0
O3—C8—H8C109.5C24—C25—H25120.0
H8A—C8—H8C109.5N2—C26—C25122.97 (10)
H8B—C8—H8C109.5N2—C26—H26118.5
C10—C9—C14119.04 (10)C25—C26—H26118.5
C10—C9—C15117.96 (10)C19—C27—C28118.18 (9)
C14—C9—C15122.98 (10)C19—C27—H27A107.8
C11—C10—C9121.19 (10)C28—C27—H27A107.8
C11—C10—H10119.4C19—C27—H27B107.8
C9—C10—H10119.4C28—C27—H27B107.8
C10—C11—C12119.11 (10)H27A—C27—H27B107.1
C10—C11—H11120.4C27—C28—C29108.07 (9)
C12—C11—H11120.4C27—C28—H28A110.1
O6—C12—C11124.28 (10)C29—C28—H28A110.1
O6—C12—C13115.45 (10)C27—C28—H28B110.1
C11—C12—C13120.27 (10)C29—C28—H28B110.1
C14—C13—C12119.88 (10)H28A—C28—H28B108.4
C14—C13—H13120.1C24—C29—C28117.92 (9)
C12—C13—H13120.1C24—C29—H29A107.8
C13—C14—C9120.51 (10)C28—C29—H29A107.8
C13—C14—H14119.7C24—C29—H29B107.8
C9—C14—H14119.7C28—C29—H29B107.8
O5—C15—O4123.78 (11)H29A—C29—H29B107.2
C6—C1—C2—C30.30 (16)C15—C9—C14—C13−178.28 (10)
C7—C1—C2—C3179.49 (9)C10—C9—C15—O57.14 (16)
C1—C2—C3—C4−0.95 (16)C14—C9—C15—O5−174.62 (10)
C8—O3—C4—C52.42 (14)C10—C9—C15—O4−172.09 (9)
C8—O3—C4—C3−178.29 (9)C14—C9—C15—O46.15 (15)
C2—C3—C4—O3−178.75 (9)C21—N1—C17—C180.08 (18)
C2—C3—C4—C50.57 (15)N1—C17—C18—C190.39 (19)
O3—C4—C5—C6179.70 (9)C17—C18—C19—C20−0.65 (17)
C3—C4—C5—C60.44 (15)C17—C18—C19—C27179.03 (11)
C4—C5—C6—C1−1.10 (15)C18—C19—C20—C210.48 (17)
C2—C1—C6—C50.73 (15)C27—C19—C20—C21−179.17 (11)
C7—C1—C6—C5−178.44 (9)C17—N1—C21—C20−0.26 (18)
C6—C1—C7—O2166.69 (10)C19—C20—C21—N1−0.03 (19)
C2—C1—C7—O2−12.48 (15)C26—N2—C22—C231.34 (16)
C6—C1—C7—O1−13.18 (14)N2—C22—C23—C240.23 (17)
C2—C1—C7—O1167.66 (9)C22—C23—C24—C25−1.59 (15)
C14—C9—C10—C11−0.44 (16)C22—C23—C24—C29177.80 (10)
C15—C9—C10—C11177.87 (10)C23—C24—C25—C261.39 (15)
C9—C10—C11—C120.44 (16)C29—C24—C25—C26−178.03 (10)
C16—O6—C12—C11−2.11 (16)C22—N2—C26—C25−1.55 (16)
C16—O6—C12—C13177.66 (9)C24—C25—C26—N20.18 (17)
C10—C11—C12—O6179.81 (10)C20—C19—C27—C28−2.62 (17)
C10—C11—C12—C130.04 (16)C18—C19—C27—C28177.73 (10)
O6—C12—C13—C14179.69 (10)C19—C27—C28—C29−173.98 (9)
C11—C12—C13—C14−0.52 (16)C23—C24—C29—C28−11.68 (16)
C12—C13—C14—C90.53 (16)C25—C24—C29—C28167.70 (9)
C10—C9—C14—C13−0.05 (16)C27—C28—C29—C24−170.16 (9)

4-Methoxybenzoic acid–1,3-bis(pyridin-4-yl)propane (2/1) (I)   Hydrogen-bond geometry (Å, º)

Cg2, Cg3 and Cg4 are the centroids of the N2/C22–C26, C1–C6 and C9–C14 rings, respectively.

D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.87 (2)1.71 (2)2.5730 (16)170 (3)
O4—H4A···N20.88 (2)1.80 (2)2.6721 (17)171 (2)
N1—H1B···O10.89 (2)1.69 (4)2.5730 (16)171 (5)
N2—H4B···O40.87 (2)1.80 (4)2.6720 (16)177 (7)
C17—H17···O6i0.952.483.342 (2)151
C18—H18···O2ii0.952.603.515 (2)162
C21—H21···O2iii0.952.433.2563 (19)145
C26—H26···O50.952.363.0890 (18)133
C3—H3···Cg4iv0.952.643.4265 (19)140
C5—H5···Cg2v0.952.713.5440 (18)146
C10—H10···Cg3vi0.952.893.5859 (19)131
C28—H28B···Cg4vii0.992.913.7154 (19)139

Symmetry codes: (i) x+1, y, z+1; (ii) −x+1, −y+1, −z+1; (iii) −x, −y, −z+1; (iv) x+1, y−1, z+1; (v) −x, −y+1, −z+1; (vi) x, y+1, z−1; (vii) −x, −y+1, −z.

Biphenyl-4,4'-dicarboxylic acid–4-methoxypyridine (1/2) (II)   Crystal data

C14H9.43O4·C6H7.32NO·C6H7.25NOF(000) = 968.00
Mr = 460.47Dx = 1.395 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71075 Å
a = 18.354 (6) ÅCell parameters from 20884 reflections
b = 7.4166 (16) Åθ = 3.0–33.0°
c = 16.674 (5) ŵ = 0.10 mm1
β = 104.943 (12)°T = 93 K
V = 2192.9 (10) Å3Block, colorless
Z = 40.45 × 0.40 × 0.35 mm

Biphenyl-4,4'-dicarboxylic acid–4-methoxypyridine (1/2) (II)   Data collection

Rigaku R-AXIS RAPID II diffractometer4085 reflections with I > 2σ(I)
Detector resolution: 10.000 pixels mm-1Rint = 0.035
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: numerical (NUMABS; Higashi, 1999)h = −23→23
Tmin = 0.963, Tmax = 0.966k = −8→9
20851 measured reflectionsl = −21→21
5026 independent reflections

Biphenyl-4,4'-dicarboxylic acid–4-methoxypyridine (1/2) (II)   Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: mixed
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0656P)2 + 0.1824P] where P = (Fo2 + 2Fc2)/3
5026 reflections(Δ/σ)max = 0.001
323 parametersΔρmax = 0.35 e Å3
4 restraintsΔρmin = −0.26 e Å3

Biphenyl-4,4'-dicarboxylic acid–4-methoxypyridine (1/2) (II)   Special details

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. Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences.

Biphenyl-4,4'-dicarboxylic acid–4-methoxypyridine (1/2) (II)   Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
O10.50808 (4)0.28798 (11)0.54421 (5)0.02581 (19)
H1A0.4857 (13)0.300 (3)0.5837 (12)0.039*0.68 (3)
O20.59317 (5)0.45187 (11)0.63520 (5)0.02892 (19)
O30.97286 (4)0.40830 (10)0.19753 (5)0.02486 (18)
H3A0.9981 (11)0.387 (3)0.1612 (11)0.037*0.75 (3)
O40.89523 (5)0.21022 (11)0.11695 (5)0.02858 (19)
O50.31541 (4)0.32860 (10)0.83543 (5)0.02399 (18)
O61.16611 (4)0.33625 (10)−0.09371 (5)0.02332 (18)
N10.43554 (5)0.29753 (12)0.65825 (6)0.0224 (2)
H1B0.457 (2)0.279 (6)0.618 (2)0.034*0.32 (3)
N21.05080 (5)0.36571 (12)0.08839 (6)0.0214 (2)
H3B1.029 (3)0.375 (8)0.130 (3)0.032*0.25 (3)
C10.61880 (6)0.37495 (13)0.50687 (6)0.0189 (2)
C20.68583 (6)0.47177 (14)0.52414 (6)0.0209 (2)
H20.69970.54360.57290.025*
C30.73242 (6)0.46464 (14)0.47108 (6)0.0217 (2)
H30.77830.53080.48440.026*
C40.71359 (6)0.36215 (13)0.39803 (6)0.0174 (2)
C50.64529 (6)0.26812 (15)0.38096 (7)0.0234 (2)
H50.63050.19860.33160.028*
C60.59875 (6)0.27387 (15)0.43431 (7)0.0244 (2)
H60.55270.20820.42120.029*
C70.57184 (6)0.37705 (13)0.56804 (6)0.0200 (2)
C80.86113 (6)0.32919 (13)0.23465 (6)0.0194 (2)
C90.79105 (6)0.24541 (14)0.21431 (6)0.0214 (2)
H90.77570.17880.16410.026*
C100.74320 (6)0.25758 (14)0.26609 (6)0.0206 (2)
H100.69540.20000.25050.025*
C110.76402 (6)0.35335 (13)0.34110 (6)0.0178 (2)
C120.83442 (6)0.43886 (14)0.36029 (7)0.0224 (2)
H120.84990.50570.41040.027*
C130.88208 (6)0.42841 (14)0.30799 (7)0.0222 (2)
H130.92920.48920.32220.027*
C140.91111 (6)0.30991 (13)0.17715 (7)0.0204 (2)
C150.37013 (6)0.21013 (14)0.65102 (7)0.0233 (2)
H150.35080.13890.60290.028*
C160.32982 (6)0.21856 (14)0.70967 (7)0.0232 (2)
H160.28390.15380.70230.028*
C170.35741 (6)0.32408 (13)0.78043 (6)0.0198 (2)
C180.42461 (6)0.41775 (14)0.78814 (6)0.0222 (2)
H180.44480.49210.83500.027*
C190.46117 (6)0.39954 (15)0.72562 (7)0.0240 (2)
H190.50710.46320.73090.029*
C200.34345 (7)0.43321 (17)0.90933 (7)0.0282 (2)
H20A0.30740.42800.94360.042*
H20B0.35000.55870.89420.042*
H20C0.39210.38430.94060.042*
C211.11352 (6)0.46206 (14)0.09146 (7)0.0240 (2)
H211.13210.53910.13770.029*
C221.15210 (6)0.45467 (14)0.03100 (7)0.0236 (2)
H221.19590.52620.03530.028*
C231.12592 (6)0.34022 (13)−0.03684 (6)0.0192 (2)
C241.06118 (6)0.23911 (14)−0.04050 (7)0.0210 (2)
H241.04180.1591−0.08550.025*
C251.02579 (6)0.25802 (14)0.02294 (7)0.0221 (2)
H250.98110.19050.01970.027*
C261.13950 (7)0.21987 (15)−0.16463 (7)0.0261 (2)
H26A1.08870.2570−0.19520.039*
H26B1.13820.0950−0.14580.039*
H26C1.17360.2285−0.20110.039*

Biphenyl-4,4'-dicarboxylic acid–4-methoxypyridine (1/2) (II)   Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0224 (4)0.0336 (4)0.0239 (4)−0.0043 (3)0.0104 (3)−0.0059 (3)
O20.0271 (4)0.0399 (5)0.0216 (4)−0.0053 (3)0.0095 (3)−0.0067 (3)
O30.0229 (4)0.0294 (4)0.0249 (4)−0.0019 (3)0.0108 (3)−0.0029 (3)
O40.0351 (5)0.0281 (4)0.0277 (4)−0.0069 (3)0.0176 (4)−0.0069 (3)
O50.0257 (4)0.0266 (4)0.0228 (4)−0.0030 (3)0.0119 (3)−0.0018 (3)
O60.0227 (4)0.0254 (4)0.0245 (4)−0.0023 (3)0.0109 (3)−0.0028 (3)
N10.0239 (5)0.0245 (4)0.0211 (4)0.0038 (4)0.0096 (4)0.0032 (4)
N20.0214 (4)0.0209 (4)0.0237 (5)0.0025 (3)0.0092 (4)0.0015 (3)
C10.0203 (5)0.0185 (5)0.0182 (5)0.0041 (4)0.0057 (4)0.0032 (4)
C20.0238 (5)0.0215 (5)0.0170 (4)0.0001 (4)0.0047 (4)−0.0017 (4)
C30.0202 (5)0.0240 (5)0.0207 (5)−0.0034 (4)0.0051 (4)−0.0012 (4)
C40.0187 (5)0.0161 (4)0.0172 (5)0.0037 (4)0.0044 (4)0.0027 (4)
C50.0243 (5)0.0260 (5)0.0209 (5)−0.0037 (4)0.0076 (4)−0.0057 (4)
C60.0212 (5)0.0290 (5)0.0245 (5)−0.0053 (4)0.0083 (4)−0.0051 (4)
C70.0198 (5)0.0209 (5)0.0196 (5)0.0037 (4)0.0055 (4)0.0025 (4)
C80.0222 (5)0.0178 (4)0.0194 (5)0.0029 (4)0.0075 (4)0.0030 (4)
C90.0238 (5)0.0227 (5)0.0172 (5)0.0002 (4)0.0047 (4)−0.0021 (4)
C100.0186 (5)0.0229 (5)0.0201 (5)−0.0010 (4)0.0047 (4)−0.0004 (4)
C110.0191 (5)0.0160 (4)0.0183 (5)0.0033 (4)0.0051 (4)0.0024 (4)
C120.0239 (5)0.0231 (5)0.0209 (5)−0.0020 (4)0.0069 (4)−0.0043 (4)
C130.0205 (5)0.0234 (5)0.0233 (5)−0.0026 (4)0.0072 (4)−0.0014 (4)
C140.0232 (5)0.0182 (5)0.0210 (5)0.0020 (4)0.0081 (4)0.0031 (4)
C150.0288 (6)0.0205 (5)0.0209 (5)0.0009 (4)0.0071 (4)−0.0004 (4)
C160.0246 (5)0.0206 (5)0.0255 (5)−0.0026 (4)0.0087 (4)0.0003 (4)
C170.0215 (5)0.0191 (5)0.0203 (5)0.0037 (4)0.0082 (4)0.0048 (4)
C180.0211 (5)0.0254 (5)0.0199 (5)0.0004 (4)0.0051 (4)0.0008 (4)
C190.0213 (5)0.0279 (5)0.0234 (5)0.0007 (4)0.0070 (4)0.0022 (4)
C200.0280 (6)0.0383 (6)0.0206 (5)−0.0024 (5)0.0103 (4)−0.0039 (5)
C210.0244 (5)0.0237 (5)0.0249 (5)−0.0014 (4)0.0077 (4)−0.0042 (4)
C220.0204 (5)0.0230 (5)0.0280 (5)−0.0031 (4)0.0075 (4)−0.0021 (4)
C230.0184 (5)0.0181 (5)0.0222 (5)0.0042 (4)0.0070 (4)0.0038 (4)
C240.0204 (5)0.0201 (5)0.0226 (5)−0.0006 (4)0.0057 (4)−0.0003 (4)
C250.0198 (5)0.0200 (5)0.0270 (5)−0.0002 (4)0.0069 (4)0.0032 (4)
C260.0307 (6)0.0246 (5)0.0255 (5)−0.0005 (4)0.0114 (5)−0.0036 (4)

Biphenyl-4,4'-dicarboxylic acid–4-methoxypyridine (1/2) (II)   Geometric parameters (Å, º)

O1—C71.3130 (13)C9—C101.3841 (15)
O1—H1A0.866 (17)C9—H90.9500
O2—C71.2202 (13)C10—C111.4029 (14)
O3—C141.3168 (13)C10—H100.9500
O3—H3A0.868 (16)C11—C121.4003 (15)
O4—C141.2198 (13)C12—C131.3875 (15)
O5—C171.3420 (13)C12—H120.9500
O5—C201.4345 (13)C13—H130.9500
O6—C231.3435 (13)C15—C161.3715 (16)
O6—C261.4436 (13)C15—H150.9500
N1—C191.3353 (15)C16—C171.3974 (15)
N1—C151.3422 (15)C16—H160.9500
N1—H1B0.88 (2)C17—C181.3924 (15)
N2—C251.3347 (14)C18—C191.3841 (16)
N2—C211.3446 (15)C18—H180.9500
N2—H3B0.88 (2)C19—H190.9500
C1—C21.3890 (15)C20—H20A0.9800
C1—C61.3899 (15)C20—H20B0.9800
C1—C71.4955 (15)C20—H20C0.9800
C2—C31.3809 (15)C21—C221.3743 (16)
C2—H20.9500C21—H210.9500
C3—C41.4013 (14)C22—C231.3967 (15)
C3—H30.9500C22—H220.9500
C4—C51.3981 (15)C23—C241.3931 (15)
C4—C111.4885 (15)C24—C251.3838 (16)
C5—C61.3837 (15)C24—H240.9500
C5—H50.9500C25—H250.9500
C6—H60.9500C26—H26A0.9800
C8—C91.3894 (15)C26—H26B0.9800
C8—C131.3937 (15)C26—H26C0.9800
C8—C141.4949 (15)
C7—O1—H1A106.0 (15)C12—C13—H13119.8
C14—O3—H3A107.3 (14)C8—C13—H13119.8
C17—O5—C20117.29 (9)O4—C14—O3123.73 (10)
C23—O6—C26117.38 (8)O4—C14—C8121.99 (10)
C19—N1—C15117.52 (10)O3—C14—C8114.27 (9)
C19—N1—H1B127 (3)N1—C15—C16123.26 (10)
C15—N1—H1B115 (3)N1—C15—H15118.4
C25—N2—C21117.36 (10)C16—C15—H15118.4
C25—N2—H3B124 (4)C15—C16—C17118.88 (10)
C21—N2—H3B119 (4)C15—C16—H16120.6
C2—C1—C6118.75 (10)C17—C16—H16120.6
C2—C1—C7119.25 (9)O5—C17—C18125.15 (10)
C6—C1—C7121.97 (9)O5—C17—C16116.36 (9)
C3—C2—C1120.60 (9)C18—C17—C16118.48 (10)
C3—C2—H2119.7C19—C18—C17118.15 (10)
C1—C2—H2119.7C19—C18—H18120.9
C2—C3—C4121.53 (10)C17—C18—H18120.9
C2—C3—H3119.2N1—C19—C18123.71 (10)
C4—C3—H3119.2N1—C19—H19118.1
C5—C4—C3117.05 (9)C18—C19—H19118.1
C5—C4—C11121.38 (9)O5—C20—H20A109.5
C3—C4—C11121.57 (9)O5—C20—H20B109.5
C6—C5—C4121.57 (10)H20A—C20—H20B109.5
C6—C5—H5119.2O5—C20—H20C109.5
C4—C5—H5119.2H20A—C20—H20C109.5
C5—C6—C1120.49 (10)H20B—C20—H20C109.5
C5—C6—H6119.8N2—C21—C22123.29 (10)
C1—C6—H6119.8N2—C21—H21118.4
O2—C7—O1123.81 (10)C22—C21—H21118.4
O2—C7—C1121.71 (10)C21—C22—C23118.92 (10)
O1—C7—C1114.45 (9)C21—C22—H22120.5
C9—C8—C13118.61 (10)C23—C22—H22120.5
C9—C8—C14118.90 (9)O6—C23—C24125.08 (9)
C13—C8—C14122.50 (9)O6—C23—C22116.62 (9)
C10—C9—C8121.00 (10)C24—C23—C22118.30 (10)
C10—C9—H9119.5C25—C24—C23118.37 (10)
C8—C9—H9119.5C25—C24—H24120.8
C9—C10—C11121.21 (10)C23—C24—H24120.8
C9—C10—H10119.4N2—C25—C24123.75 (10)
C11—C10—H10119.4N2—C25—H25118.1
C12—C11—C10117.15 (10)C24—C25—H25118.1
C12—C11—C4121.55 (9)O6—C26—H26A109.5
C10—C11—C4121.30 (9)O6—C26—H26B109.5
C13—C12—C11121.68 (10)H26A—C26—H26B109.5
C13—C12—H12119.2O6—C26—H26C109.5
C11—C12—H12119.2H26A—C26—H26C109.5
C12—C13—C8120.33 (10)H26B—C26—H26C109.5
C6—C1—C2—C3−1.35 (15)C9—C8—C13—C121.60 (15)
C7—C1—C2—C3176.47 (9)C14—C8—C13—C12−178.50 (9)
C1—C2—C3—C40.75 (15)C9—C8—C14—O4−6.65 (15)
C2—C3—C4—C50.35 (15)C13—C8—C14—O4173.45 (10)
C2—C3—C4—C11−179.56 (9)C9—C8—C14—O3173.64 (9)
C3—C4—C5—C6−0.85 (15)C13—C8—C14—O3−6.26 (14)
C11—C4—C5—C6179.06 (10)C19—N1—C15—C16−1.16 (15)
C4—C5—C6—C10.25 (17)N1—C15—C16—C170.51 (16)
C2—C1—C6—C50.86 (16)C20—O5—C17—C18−2.33 (14)
C7—C1—C6—C5−176.90 (9)C20—O5—C17—C16178.78 (9)
C2—C1—C7—O2−4.87 (15)C15—C16—C17—O5179.48 (9)
C6—C1—C7—O2172.88 (10)C15—C16—C17—C180.51 (15)
C2—C1—C7—O1177.12 (9)O5—C17—C18—C19−179.69 (9)
C6—C1—C7—O1−5.13 (14)C16—C17—C18—C19−0.81 (15)
C13—C8—C9—C10−0.89 (15)C15—N1—C19—C180.82 (15)
C14—C8—C9—C10179.21 (9)C17—C18—C19—N10.15 (16)
C8—C9—C10—C11−0.58 (15)C25—N2—C21—C220.17 (15)
C9—C10—C11—C121.30 (15)N2—C21—C22—C23−0.80 (16)
C9—C10—C11—C4−178.20 (9)C26—O6—C23—C240.86 (14)
C5—C4—C11—C12−176.28 (10)C26—O6—C23—C22−179.47 (9)
C3—C4—C11—C123.63 (14)C21—C22—C23—O6−179.22 (9)
C5—C4—C11—C103.20 (14)C21—C22—C23—C240.47 (15)
C3—C4—C11—C10−176.89 (9)O6—C23—C24—C25−179.92 (9)
C10—C11—C12—C13−0.58 (15)C22—C23—C24—C250.42 (14)
C4—C11—C12—C13178.92 (9)C21—N2—C25—C240.82 (15)
C11—C12—C13—C8−0.87 (16)C23—C24—C25—N2−1.12 (15)

Biphenyl-4,4'-dicarboxylic acid–4-methoxypyridine (1/2) (II)   Hydrogen-bond geometry (Å, º)

Cg2 and Cg4 are the centroids of the C8–C13 and N2/C21–C25 rings, respectively.

D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.87 (2)1.73 (2)2.5882 (15)173 (2)
O3—H3A···N20.87 (2)1.74 (2)2.6078 (15)175 (2)
N1—H1B···O10.88 (2)1.73 (5)2.5882 (16)167 (5)
N2—H3B···O30.88 (2)1.74 (6)2.6077 (15)169 (5)
C10—H10···O2i0.952.573.4146 (17)148
C19—H19···O20.952.523.1901 (17)128
C20—H20A···O6ii0.982.603.3210 (18)131
C25—H25···O40.952.543.2035 (17)127
C26—H26B···O4iii0.982.433.3874 (17)167
C12—H12···Cg4iv0.952.903.6968 (16)142
C21—H21···Cg2iv0.952.643.5284 (16)155

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

References

  • Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609–613.
  • Cruz, C., Delgado, R., Drew, M. G. B. & Felix, V. (2004). Org. Biomol. Chem. 2, 2911–2918. [PubMed]
  • Du, M., You, Y.-P. & Zhang, Z.-H. (2006). Acta Cryst. C62, o33–o35. [PubMed]
  • Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.
  • Gong, H.-Y., Rambo, B. M., Karnas, E., Lynch, V. M., Keller, K. M. & Sessler, J. L. (2011). J. Am. Chem. Soc. 133, 1526–1533. [PubMed]
  • Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. [PMC free article] [PubMed]
  • Grunert, M., Howie, A., Kaeding, A. & Imrie, C. T. (1997). J. Mater. Chem. 7, 211–214.
  • Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
  • Kato, T., Fréchet, J. M. J., Wilson, P. G., Saito, T., Uryu, T., Fujishima, A., Jin, C. & Kaneuchi, F. (1993). Chem. Mater. 5, 1094–1100.
  • Kato, T., Wilson, P. G., Fujishima, A. & Fréchet, J. M. J. (1990). Chem. Lett. pp. 2003–2006.
  • Mukherjee, A. & Desiraju, G. R. (2014). Cryst. Growth Des. 14, 1375–1385.
  • Ramon, G., Davies, K. & Nassimbeni, L. R. (2014). CrstEngComm, 16, 5802–5810.
  • Rigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
  • Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. [PMC free article] [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Tabuchi, Y., Gotoh, K. & Ishida, H. (2015a). Acta Cryst. E71, 1290–1295.
  • Tabuchi, Y., Gotoh, K. & Ishida, H. (2015b). Acta Cryst. E71, 1340–1344.
  • Tabuchi, Y., Gotoh, K. & Ishida, H. (2016a). Acta Cryst. E72, 1666–1671.
  • Tabuchi, Y., Gotoh, K. & Ishida, H. (2016b). Acta Cryst. E72, 1771–1775.

Articles from Acta Crystallographica Section E: Crystallographic Communications are provided here courtesy of International Union of Crystallography