The authors wish to acknowledge the SAIF, IIT, Madras, for the data collection.Peer reviewe

Chakkaravarthi, G.

Kumar, M.K.

Kumar, R.M.

Pandi, P.

Sudhahar, S.

Acta Crystallographica Section E Structure Reports Online

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The Open University

Crystal structure of 4-aminobenzoicacid–4-methylpyridine (1/1)M. Krishna Kumar,a P. Pandi,b S. Sudhahar,aG. Chakkaravarthic* and R. Mohan Kumara*aDepartment of Physics, Presidency College, Chennai 600 005, India, bDepartmentof Physics, Panimalar Engineering College, Chennai 600 123, India, andcDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India.*Correspondence e-mail: chakkaravarthi_2005@yahoo.com,mohan66@hotmail.comReceived 2 January 2015; accepted 14 January 2015Edited by W. T. A. Harrison, University of Aberdeen, ScotlandIn the title 1:1 adduct, C6H7NC7H7NO2, the carboxylic acidgroup is twisted at an angle of 4.32 (18) with respect to theattached benzene ring. In the crystal, the carboxylic acid groupis linked to the pyridine ring by an O—H  N hydrogen bond,forming a dimer. The dimers are linked by N—H  Ohydrogen bonds, generating (010) sheets.Keywords: crystal structure; adduct; O—H  N and N—H  O hydrogenbonds; layered structure.CCDC reference: 10435921. Related literatureFor background to pyridine derivatives, see: Tomaru et al.(1991). Katritzky et al. (1996); Akkurt et al. (2005). For relatedstructures, see: Smith & Wermuth (2010); Hemamalini & Fun(2010); Kannan et al. (2012); Thanigaimani et al. (2012);Muralidharan et al. (2013).2. Experimental2.1. Crystal dataC6H7NC7H7NO2Mr = 230.26Monoclinic, Pca = 7.5970 (7) Åb = 11.6665 (12) Åc = 7.6754 (8) Å = 114.200 (3)V = 620.49 (11) Å3Z = 2Mo K radiation = 0.09 mm1T = 295 K0.28  0.24  0.20 mm2.2. Data collectionBruker Kappa APEXII CCDdiffractometerAbsorption correction: multi-scan(SADABS; Sheldrick, 1996)Tmin = 0.977, Tmax = 0.98310064 measured reflections2144 independent reflections1458 reflections with I > 2(I)Rint = 0.0302.3. RefinementR[F 2 > 2(F 2)] = 0.038wR(F 2) = 0.108S = 1.032144 reflections159 parameters3 restraintsH atoms treated by a mixture ofindependent and constrainedrefinementmax = 0.12 e Å3min = 0.13 e Å3Table 1Hydrogen-bond geometry (Å, ).D—H  A D—H H  A D  A D—H  AO1—H1  N2i 0.84 (1) 1.81 (1) 2.644 (3) 177 (4)N1—H1A  O2ii 0.86 2.32 3.049 (3) 142N1—H1B  O2iii 0.86 2.17 3.031 (3) 174Symmetry codes: (i) x þ 1; y; z; (ii) x 1; y; z 1; (iii) x 1;y; z 12.Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT(Bruker, 2004); data reduction: SAINT; program(s) used to solvestructure: SHELXS97 (Sheldrick, 2008); program(s) used to refinestructure: SHELXL97 (Sheldrick, 2015); molecular graphics:PLATON (Spek, 2009); software used to prepare material forpublication: SHELXL97.AcknowledgementsThe authors wish to acknowledge the SAIF, IIT, Madras, forthe data collection.Supporting information for this paper is available from the IUCrelectronic archives (Reference: HB7348).ReferencesAkkurt, M., Karaca, S., Jarrahpour, A. A., Zarei, M. & Büyükgüngör, O.(2005). Acta Cryst. E61, o776–o778.Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin,USA.Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o2151–o2152.Kannan, V., Sugumar, P., Brahadeeswaran, S. & Ponnuswamy, M. N. (2012).Acta Cryst. E68, o3187.Katritzky, A. R., Rees, C. W. & Scriven, E. F. V. (1996). In ComprehensiveHeterocyclic Chemistry II. Oxford: Pergamon Press.data reportsActa Cryst. (2015). E71, o125–o126 doi:10.1107/S2056989015000791 Kumar et al. o125ISSN 2056-9890CORE Metadata, citation and similar papers at core.ac.ukProvided by Aberdeen University Research ArchiveMuralidharan, S., Elavarasu, N., Srinivasan, T., Gopalakrishnan, R. &Velmurugan, D. (2013). Acta Cryst. E69, o910.Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8.Smith, G. & Wermuth, U. D. (2010). Acta Cryst. E66, o1254.Spek, A. L. (2009). Acta Cryst. D65, 148–155.Thanigaimani, K., Farhadikoutenaei, A., Khalib, N. C., Arshad, S. & Razak,I. A. (2012). Acta Cryst. E68, o3196–o3197.Tomaru, S., Matsumoto, S., Kurihara, T., Suzuki, H., Ooba, N. & Kaino,T. (1991). Appl. Phys. Lett. 58, 2583–2585.data reportso126 Kumar et al.  C6H7NC7H7NO2 Acta Cryst. (2015). E71, o125–o126supporting informationsup-1Acta Cryst. (2015). E71, o125–o126    supporting informationActa Cryst. (2015). E71, o125–o126    [doi:10.1107/S2056989015000791]Crystal structure of 4-aminobenzoic acid–4-methylpyridine (1/1)M. Krishna Kumar, P. Pandi, S. Sudhahar, G. Chakkaravarthi and R. Mohan KumarS1. Chemical context Aminopyridine and its derivatives play an important role in heterocyclic chemistry (Katritzky et al., 1996). Some pyridine derivatives possess nonlinear optical (NLO) properties (Tomaru et al., 1991) and possess antibacterial and anti-fungal activities (Akkurt et al., 2005). we herewith, report the synthesis and the crystal structure of (I) (Fig. 1). S2. Structural commentary The molecular structure of the title compound (I) is shown in (Fig. 1). It consists of two independent molecules in the assymetric unit. In the 4-aminobenzoic acid molecule, the carboxyl group is twisted at an angle of 4.32 (18)° with respect to the aromatic ring. In the 4-methylpyridine molecule, the pyridine ring (C8—C12/N2) is almost planar [maximum deviation 0.002 (3) Å]. The dihedral angle between the benzene ring (C1—C6) and pyridine ring (C8—C12/N2) is 57.11 (14)°. S3. Supramolecular features In the crystal structure, 4-aminobenzoate and 4-methylpyridine molecules are linked by weak intermolecular O—H···N hydrogen bonds and forms infinite one-dimensional chain along [0 0 1]. The adjacent 4-aminobenzoate molecules are connected by weak intermolecular N—H···O hydrogen bonds, forming R22(12) ring motif in a two-dimensional network in the (010) plane (Table 2 & Fig. 2). S4. Database survey Several similar structures containing methylpyridinium and nitrobenzoate molecules have been reported earlier: i.e., 2-Amino-5-methylpyridinium 2-aminobenzoate (Thanigaimani et al., 2012); 2-Amino-5-chloropyridinium 4-amino-benzoate (Kannan et al., 2012); 2-Amino-4-methylpyridinium 2-nitrobenzoate (Muralidharan et al., 2013); 4-Methyl-pyridinium 2-carboxy-4,5-dichlorobenzoate monohydrate [Smith & Wermuth, (2010)]; 2-Amino-4-methylpyridinium 2-hydroxybenzoate [Hemamalini & Fun (2010)]. S5. Synthesis and crystallization Equimolar quantity of 4-methylpyridine and 4-aminobenzoic acid were dissolved in methanol-water mixed solvent and colourless blocks of the title adduct were grown by slow evaporation of the solvents. S6. Refinement Crystal data, data collection and structure refinement details are summarized in Table 1. The hydrogen atoms attached to C atoms and N atom were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic) or 0.96 Å (methyl) and N—H = 0.86 Å with Uiso(H) = 1.2 Ueq(C or N) or 1.5 Ueq(C) The hydroxyl H atom was located in a difference Fourier map, and refined with Uiso(H) = 1.2 Ueq(O) and distance restraint O—H = 0.82 Å. supporting informationsup-2Acta Cryst. (2015). E71, o125–o126    Figure 1The molecular structure of (I), with 30% probability displacement ellipsoids for non-H atoms. 4-Aminobenzoic acid–4-methylpyridine (1/1) Crystal data C6H7N·C7H7NO2Mr = 230.26Monoclinic, PcHall symbol: P -2yca = 7.5970 (7) Åb = 11.6665 (12) Åc = 7.6754 (8) Åβ = 114.200 (3)°V = 620.49 (11) Å3Z = 2F(000) = 244Dx = 1.232 Mg m−3Mo Kα radiation, λ = 0.71073 ÅCell parameters from 2749 reflectionsθ = 3.4–21.8°µ = 0.09 mm−1T = 295 KBlock, colourless0.28 × 0.24 × 0.20 mmsupporting informationsup-3Acta Cryst. (2015). E71, o125–o126    Data collection Bruker Kappa APEXII CCD diffractometerRadiation source: fine-focus sealed tubeGraphite monochromatorω and φ scanAbsorption correction: multi-scan (SADABS; Sheldrick, 1996)Tmin = 0.977, Tmax = 0.98310064 measured reflections2144 independent reflections1458 reflections with I > 2σ(I)Rint = 0.030θmax = 26.7°, θmin = 3.4°h = −9→8k = −14→14l = −9→9Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.038wR(F2) = 0.108S = 1.032144 reflections159 parameters3 restraintsPrimary atom site location: structure-invariant direct methodsSecondary atom site location: difference Fourier mapHydrogen site location: inferred from neighbouring sitesH atoms treated by a mixture of independent and constrained refinementw = 1/[σ2(Fo2) + (0.0554P)2 + 0.0229P] where P = (Fo2 + 2Fc2)/3(Δ/σ)max < 0.001Δρmax = 0.12 e Å−3Δρmin = −0.13 e Å−3Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4Extinction coefficient: 0.013 (4)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. 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.Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) x y z Uiso*/UeqC1 0.3693 (4) 0.1034 (2) 0.7149 (4) 0.0567 (6)C2 0.4434 (4) 0.2029 (2) 0.6722 (4) 0.0591 (7)H2 0.3671 0.2471 0.5675 0.071*C3 0.6273 (4) 0.2362 (2) 0.7829 (3) 0.0558 (6)H3 0.6737 0.3037 0.7529 0.067*C4 0.7475 (4) 0.1730 (2) 0.9383 (4) 0.0508 (6)C5 0.6737 (4) 0.0738 (2) 0.9798 (4) 0.0594 (7)H5 0.7516 0.0294 1.0835 0.071*C6 0.4892 (4) 0.0392 (2) 0.8724 (4) 0.0629 (7)H6 0.4429 −0.0278 0.9043 0.076*C7 0.9416 (4) 0.2104 (2) 1.0596 (4) 0.0587 (7)C8 0.4371 (5) 0.4546 (2) 1.3188 (5) 0.0729 (8)H8 0.3567 0.5148 1.3183 0.087*C9 0.6306 (4) 0.4655 (2) 1.4263 (4) 0.0693 (8)H9 0.6791 0.5319 1.4967 0.083*supporting informationsup-4Acta Cryst. (2015). E71, o125–o126    C10 0.7534 (4) 0.3784 (2) 1.4304 (4) 0.0639 (7)C11 0.6716 (4) 0.2836 (2) 1.3242 (4) 0.0718 (8)H11 0.7487 0.2220 1.3229 0.086*C12 0.4767 (5) 0.2790 (3) 1.2196 (4) 0.0766 (9)H12 0.4249 0.2135 1.1479 0.092*C13 0.9658 (5) 0.3866 (3) 1.5468 (6) 0.0954 (11)H13A 1.0310 0.3941 1.4635 0.143*H13B 1.0099 0.3186 1.6229 0.143*H13C 0.9930 0.4524 1.6289 0.143*N1 0.1840 (4) 0.0710 (2) 0.6087 (4) 0.0827 (8)H1A 0.1113 0.1124 0.5137 0.099*H1B 0.1395 0.0092 0.6364 0.099*N2 0.3582 (3) 0.3627 (2) 1.2152 (4) 0.0722 (6)O1 0.9921 (3) 0.30989 (17) 1.0123 (3) 0.0808 (6)H1 1.109 (2) 0.324 (3) 1.076 (5) 0.121*O2 1.0516 (3) 0.15755 (17) 1.1996 (3) 0.0778 (6)Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23C1 0.0545 (16) 0.0584 (15) 0.0526 (15) −0.0071 (14) 0.0173 (13) −0.0070 (14)C2 0.0599 (17) 0.0581 (15) 0.0489 (15) 0.0009 (12) 0.0118 (13) 0.0088 (12)C3 0.0582 (16) 0.0536 (13) 0.0509 (15) −0.0050 (13) 0.0175 (13) 0.0058 (12)C4 0.0529 (14) 0.0490 (12) 0.0442 (13) 0.0040 (12) 0.0135 (12) 0.0026 (12)C5 0.0671 (18) 0.0516 (14) 0.0484 (16) 0.0021 (13) 0.0124 (14) 0.0046 (12)C6 0.077 (2) 0.0518 (14) 0.0590 (17) −0.0076 (14) 0.0273 (15) 0.0048 (13)C7 0.0563 (17) 0.0532 (13) 0.0583 (17) 0.0045 (13) 0.0150 (14) 0.0003 (14)C8 0.0630 (18) 0.0626 (16) 0.081 (2) 0.0031 (15) 0.0172 (16) 0.0007 (16)C9 0.068 (2) 0.0617 (17) 0.0665 (19) −0.0085 (14) 0.0150 (16) −0.0042 (13)C10 0.0579 (18) 0.0740 (17) 0.0585 (17) −0.0045 (16) 0.0225 (14) 0.0063 (15)C11 0.0680 (19) 0.0723 (18) 0.078 (2) 0.0015 (15) 0.0325 (18) −0.0048 (16)C12 0.077 (2) 0.0747 (19) 0.074 (2) −0.0158 (17) 0.0260 (17) −0.0171 (16)C13 0.0604 (19) 0.105 (2) 0.104 (3) −0.0070 (17) 0.0163 (18) 0.002 (2)N1 0.0655 (16) 0.0852 (18) 0.0809 (18) −0.0163 (13) 0.0132 (14) 0.0063 (15)N2 0.0567 (14) 0.0719 (15) 0.0766 (16) −0.0059 (13) 0.0157 (12) −0.0023 (13)O1 0.0588 (11) 0.0691 (12) 0.0883 (16) −0.0105 (10) 0.0035 (11) 0.0130 (11)O2 0.0678 (13) 0.0726 (12) 0.0665 (12) 0.0068 (10) 0.0006 (10) 0.0090 (10)Geometric parameters (Å, º) C1—N1 1.359 (4) C8—H8 0.9300C1—C2 1.387 (3) C9—C10 1.371 (4)C1—C6 1.397 (4) C9—H9 0.9300C2—C3 1.361 (4) C10—C11 1.363 (4)C2—H2 0.9300 C10—C13 1.493 (5)C3—C4 1.380 (3) C11—C12 1.366 (4)C3—H3 0.9300 C11—H11 0.9300C4—C5 1.379 (3) C12—N2 1.319 (4)supporting informationsup-5Acta Cryst. (2015). E71, o125–o126    C4—C7 1.452 (3) C12—H12 0.9300C5—C6 1.364 (4) C13—H13A 0.9600C5—H5 0.9300 C13—H13B 0.9600C6—H6 0.9300 C13—H13C 0.9600C7—O2 1.224 (3) N1—H1A 0.8600C7—O1 1.319 (3) N1—H1B 0.8600C8—N2 1.323 (3) O1—H1 0.836 (10)C8—C9 1.365 (4)N1—C1—C2 120.8 (2) C8—C9—C10 119.9 (3)N1—C1—C6 121.2 (2) C8—C9—H9 120.0C2—C1—C6 118.0 (2) C10—C9—H9 120.0C3—C2—C1 120.2 (2) C11—C10—C9 116.6 (3)C3—C2—H2 119.9 C11—C10—C13 121.7 (3)C1—C2—H2 119.9 C9—C10—C13 121.7 (3)C2—C3—C4 122.2 (2) C10—C11—C12 120.2 (3)C2—C3—H3 118.9 C10—C11—H11 119.9C4—C3—H3 118.9 C12—C11—H11 119.9C5—C4—C3 117.4 (2) N2—C12—C11 123.4 (3)C5—C4—C7 120.4 (2) N2—C12—H12 118.3C3—C4—C7 122.1 (2) C11—C12—H12 118.3C6—C5—C4 121.5 (2) C10—C13—H13A 109.5C6—C5—H5 119.2 C10—C13—H13B 109.5C4—C5—H5 119.2 H13A—C13—H13B 109.5C5—C6—C1 120.6 (2) C10—C13—H13C 109.5C5—C6—H6 119.7 H13A—C13—H13C 109.5C1—C6—H6 119.7 H13B—C13—H13C 109.5O2—C7—O1 120.9 (3) C1—N1—H1A 120.0O2—C7—C4 124.1 (2) C1—N1—H1B 120.0O1—C7—C4 115.0 (2) H1A—N1—H1B 120.0N2—C8—C9 123.3 (3) C12—N2—C8 116.6 (3)N2—C8—H8 118.4 C7—O1—H1 112 (3)C9—C8—H8 118.4N1—C1—C2—C3 178.1 (3) C3—C4—C7—O2 179.2 (3)C6—C1—C2—C3 −0.5 (4) C5—C4—C7—O1 −176.1 (2)C1—C2—C3—C4 0.9 (4) C3—C4—C7—O1 1.3 (3)C2—C3—C4—C5 −0.5 (4) N2—C8—C9—C10 0.0 (5)C2—C3—C4—C7 −178.1 (2) C8—C9—C10—C11 −0.2 (4)C3—C4—C5—C6 −0.2 (4) C8—C9—C10—C13 −179.7 (3)C7—C4—C5—C6 177.4 (2) C9—C10—C11—C12 0.4 (4)C4—C5—C6—C1 0.5 (4) C13—C10—C11—C12 179.9 (3)N1—C1—C6—C5 −178.8 (3) C10—C11—C12—N2 −0.4 (5)C2—C1—C6—C5 −0.2 (4) C11—C12—N2—C8 0.1 (5)C5—C4—C7—O2 1.7 (4) C9—C8—N2—C12 0.1 (5)supporting informationsup-6Acta Cryst. (2015). E71, o125–o126    Hydrogen-bond geometry (Å, º) D—H···A D—H H···A D···A D—H···AO1—H1···N2i 0.84 (1) 1.81 (1) 2.644 (3) 177 (4)N1—H1A···O2ii 0.86 2.32 3.049 (3) 142N1—H1B···O2iii 0.86 2.17 3.031 (3) 174Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z−1; (iii) x−1, −y, z−1/2.

Crystal structure of 4-aminobenzoic acid-4-methylpyridine (1/1)

In the title 1:1 adduct, C6H7N·C7H7NO2, the carboxylic acid group is twisted at an angle of 4.32 (18)° with respect to the attached benzene ring. In the crystal, the carboxylic acid group is linked to the pyridine ring by an O—H...N hydrogen bond, forming a dimer. The dimers are linked by N—H...O hydrogen bonds, generating (010) sheets

M. Krishna Kumar

P. Pandi

S. Sudhahar

G. Chakkaravarthi

R. Mohan Kumar

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Acta Crystallographica Section E Crystallographic Communications

Crystal structure of 4-aminobenzoic acid–4-methylpyridine (1/1)

In the title 1:1 adduct, C6H7N·C7H7NO2, the carboxylic acid group is twisted at an angle of 4.32 (18)° with respect to the attached benzene ring. In the crystal, the carboxylic acid group is linked to the pyridine ring by an O—H...N hydrogen bond, forming a dimer. The dimers are linked by N—H...O hydrogen bonds, generating (010) sheets.</jats:p

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http://dx.doi.org/10.1107/S2056989015000791

Crystal structure of 4-aminobenzoic acid-4-methylpyridine (1/1)

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