3-Methyl­pyridinium 4-nitro­benzoate–4-nitro­benzoic acid (1/1)

Sivakumar, P.; Niranjana Devi, R.; Israel, S.; Chakkaravarthi, G.

doi:10.1107/S2414314616009792

organic compounds

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ISSN: 2414-3146

Volume 1| Part 6| June 2016| x160979

doi:10.1107/S2414314616009792

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3-Methylpyridinium 4-nitrobenzoate–4-nitrobenzoic acid (1/1)

P. Sivakumar,^a,^b R. Niranjana Devi,^c S. Israel ^c ^* and G. Chakkaravarthi ^b ^*

^aResearch and Development Centre, Bharathiar University, Coimbatore 641 046, India, ^bDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and ^cPost Graduate and Research Department of Physics, The American College, Madurai 625 002, India
^*Correspondence e-mail: israel.samuel@gmail.com, chakkaravarthi_2005@yahoo.com

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 13 June 2016; accepted 16 June 2016; online 21 June 2016)

In the title compound, C₆H₈N⁺·C₇H₄NO₄⁻·C₇H₅NO₄, the cation is protonated at its pyridine N atom and makes a dihedral angle of 74.14 (12)° with the benzene ring of the anion. The benzene ring of the neutral molecule and the pyridine ring are inclined at an angle of 79.20 (12)°. The two benzene rings form a dihedral angle of 6.00 (12)° with each other. In the crystal, N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds link the cations, anions and neutral molecules to form layers parallel to the ac plane, which enlose R₄⁴(18) ring motifs. The layers are linked by further C—H⋯O hydrogen bonds and C—H⋯π interactions, forming a three-dimensional supramolecular architecture.

Keywords: crystal structure; hydrogen bonding..

CCDC reference: 1485920

Structure description

Pyridine derivatives are known to exhibit pharmacological properties such as anti-inflammatory (Abdel-Alim et al., 2005 ), anticancer (Girgis et al., 2006 ) and anxiolytic (Spanka et al., 2010 ) activities. We herewith report the synthesis and the crystal structure of the title compound (Fig. 1). The geometric parameters are comparable to those of reported similar structures (Quah et al., 2008 , 2010 ).

Figure 1
The molecular structure of the title molecular salt, showing the atom labelling and 30% probability displacement ellipsoids.

The title compound contains a 3-methylpyridinium cation protonated at its N atom, a 4-nitrobenzoate deprotonated at its hydroxy O atom and a neutral 4-nitrobenzoic acid molecule. The benzene rings (C1–C6 and C8–C13) make a dihedral angle of 6.00 (12)°. The C8–C13 benzene ring of the anion forms a dihedral angle of 74.14 (12)° with the pyridine ring (N3/C15–C19) of the cation. The C1–C6 benzene ring of the neutral molecule and the pyridine ring of the caion are inclined at an angle of 79.20 (12)°.

In the crystal, N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds link the cations, anions and neutral molecules to form layers parallel to (010) (Fig. 2 and Table 1), which enclose R₄⁴(18) ring motifs (Bernstein et al., 1995 ). The layers are linked by further C—H⋯O hydrogen bonds and C—H⋯π interactions, forming a three-dimensional structure (Fig. 2 and Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the ring (C1-C6)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O4	0.88 (2)	1.73 (2)	2.612 (3)	175 (3)
O6—H6A⋯O3	0.83 (2)	1.70 (2)	2.518 (2)	175 (4)
C9—H9⋯O1ⁱ	0.93	2.47	3.271 (3)	144
C15—H15⋯O3ⁱⁱ	0.93	2.41	3.218 (3)	145
C16—H16⋯O2ⁱ	0.93	2.59	3.353 (3)	140
C19—H19⋯O5ⁱⁱⁱ	0.93	2.42	3.293 (3)	156
C13—H13⋯Cg2^iv	0.93	2.83	3.564 (3)	137
Symmetry codes: (i) x-1, y, z+1; (ii) x-1, y, z; (iii) $[-x+2, y-{\script{1\over 2}}, -z+1]$ ; (iv) $[-x+2, y+{\script{1\over 2}}, -z+1]$ .

Figure 2
The crystal packing of the title compound viewed along the a axis. The hydrogen bonds are shown as dashed lines (see Table 1

) and C-bound H atoms have been omitted for clarity.

Synthesis and crystallization

The title compound was synthesized using the raw materials 4-nitrobenzoic acid (1.67 g) and 3-methylpyridine (0.93 g) in an equimolar ratio. These reactants were dissolved in 15 ml of acetone and stirred for 4 h and the solution was kept at room temperature. After a span of 10 d, single crystals suitable for X-ray diffraction were harvested.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₆H₈N⁺·C₇H₄NO₄⁻·C₇H₅NO₄
M_r	427.37
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	295
a, b, c (Å)	6.3586 (4), 13.6276 (9), 11.7469 (8)
β (°)	104.559 (2)
V (Å³)	985.21 (11)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.11
Crystal size (mm)	0.28 × 0.24 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.969, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	17209, 4526, 3163
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.117, 1.09
No. of reflections	4526
No. of parameters	288
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.19
Absolute structure	Flack (1983 ), 2158 Friedel pairs
Absolute structure parameter	0.3 (12)
Computer programs: APEX2 and SAINT (Bruker, 2004), SHELXS97 and SHELXL97 (Sheldrick, 2008 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1485920

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2414314616009792/vm4009sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616009792/vm4009Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616009792/vm4009Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

3-Methylpyridinium 4-nitrobenzoate–4-nitrobenzoic acid (1/1) top

Crystal data top

C₆H₈N⁺·C₇H₄NO₄⁻·C₇H₅NO₄	F(000) = 444
M_r = 427.37	D_x = 1.441 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6874 reflections
a = 6.3586 (4) Å	θ = 2.3–27.7°
b = 13.6276 (9) Å	µ = 0.11 mm⁻¹
c = 11.7469 (8) Å	T = 295 K
β = 104.559 (2)°	Block, colourless
V = 985.21 (11) Å³	0.28 × 0.24 × 0.20 mm
Z = 2

Data collection top

Bruker Kappa APEXII CCD diffractometer	4526 independent reflections
Radiation source: fine-focus sealed tube	3163 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω and φ scan	θ_max = 27.9°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→8
T_min = 0.969, T_max = 0.978	k = −17→17
17209 measured reflections	l = −15→15

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 atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0465P)² + 0.1953P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
4526 reflections	Δρ_max = 0.15 e Å⁻³
288 parameters	Δρ_min = −0.19 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 2158 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.3 (12)

Special details top

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) top

	x	y	z	U_iso*/U_eq
C1	0.8161 (4)	0.49994 (17)	0.1300 (2)	0.0378 (5)
C2	0.6831 (4)	0.45484 (19)	0.0341 (2)	0.0419 (6)
H2	0.5486	0.4309	0.0386	0.050*
C3	0.7479 (4)	0.44484 (19)	−0.0690 (2)	0.0427 (5)
H3	0.6580	0.4146	−0.1344	0.051*
C4	0.9468 (4)	0.48028 (17)	−0.07302 (19)	0.0349 (5)
C5	1.0827 (4)	0.52619 (19)	0.0205 (2)	0.0449 (6)
H5	1.2168	0.5504	0.0155	0.054*
C6	1.0143 (4)	0.5356 (2)	0.1229 (2)	0.0465 (6)
H6	1.1039	0.5664	0.1878	0.056*
C7	0.7465 (4)	0.5079 (2)	0.2437 (2)	0.0470 (6)
C8	0.6962 (4)	0.72107 (17)	0.8926 (2)	0.0424 (6)
C9	0.5585 (4)	0.66743 (18)	0.8068 (2)	0.0476 (6)
H9	0.4260	0.6453	0.8170	0.057*
C10	0.6199 (4)	0.64688 (18)	0.7053 (2)	0.0457 (6)
H10	0.5279	0.6107	0.6461	0.055*
C11	0.8168 (4)	0.67933 (17)	0.6901 (2)	0.0382 (5)
C12	0.9493 (4)	0.73511 (19)	0.7767 (2)	0.0497 (6)
H12	1.0797	0.7592	0.7657	0.060*
C13	0.8912 (4)	0.7557 (2)	0.8794 (2)	0.0527 (7)
H13	0.9822	0.7924	0.9385	0.063*
C14	0.8932 (4)	0.65374 (19)	0.5837 (2)	0.0446 (6)
C15	0.2977 (4)	0.4418 (2)	0.4604 (2)	0.0528 (7)
H15	0.2215	0.4912	0.4126	0.063*
C16	0.2287 (4)	0.4086 (2)	0.5548 (3)	0.0559 (7)
H16	0.1051	0.4348	0.5719	0.067*
C17	0.3447 (4)	0.3362 (2)	0.6236 (2)	0.0543 (7)
H17	0.2990	0.3133	0.6880	0.065*
C18	0.5276 (4)	0.29665 (19)	0.5995 (2)	0.0507 (6)
C19	0.5870 (4)	0.3329 (2)	0.5033 (2)	0.0503 (6)
H19	0.7092	0.3076	0.4838	0.060*
C20	0.6584 (6)	0.2177 (2)	0.6733 (3)	0.0765 (9)
H20A	0.7627	0.1923	0.6344	0.115*
H20B	0.5636	0.1658	0.6846	0.115*
H20C	0.7328	0.2444	0.7482	0.115*
N1	1.0198 (3)	0.46793 (16)	−0.18151 (18)	0.0441 (5)
N2	0.6354 (4)	0.73877 (16)	1.0040 (2)	0.0575 (6)
N3	0.4733 (3)	0.40344 (17)	0.43743 (19)	0.0485 (5)
O1	1.1985 (3)	0.49838 (15)	−0.18295 (18)	0.0653 (6)
O2	0.8982 (3)	0.42800 (18)	−0.26438 (16)	0.0692 (6)
O3	0.8656 (3)	0.55658 (17)	0.32373 (17)	0.0701 (6)
O4	0.5771 (3)	0.4654 (2)	0.24825 (17)	0.0759 (7)
O5	1.0633 (3)	0.68184 (18)	0.56883 (18)	0.0731 (6)
O6	0.7576 (3)	0.59720 (17)	0.51037 (17)	0.0586 (5)
O7	0.7626 (4)	0.78320 (19)	1.0811 (2)	0.0873 (8)
O8	0.4619 (4)	0.70915 (19)	1.0137 (2)	0.0846 (7)
H3A	0.517 (4)	0.424 (2)	0.3758 (17)	0.067 (9)*
H6A	0.801 (6)	0.584 (3)	0.452 (2)	0.100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0390 (12)	0.0435 (13)	0.0328 (12)	0.0039 (10)	0.0126 (10)	0.0029 (10)
C2	0.0321 (11)	0.0518 (15)	0.0440 (14)	−0.0038 (11)	0.0140 (10)	0.0000 (12)
C3	0.0387 (12)	0.0508 (14)	0.0366 (12)	−0.0029 (11)	0.0060 (10)	−0.0072 (11)
C4	0.0372 (12)	0.0384 (12)	0.0305 (12)	0.0020 (9)	0.0109 (9)	0.0006 (9)
C5	0.0374 (13)	0.0540 (16)	0.0451 (15)	−0.0107 (11)	0.0138 (11)	−0.0056 (12)
C6	0.0440 (14)	0.0603 (16)	0.0348 (13)	−0.0106 (12)	0.0095 (10)	−0.0125 (12)
C7	0.0436 (14)	0.0656 (17)	0.0348 (13)	0.0092 (12)	0.0152 (11)	0.0045 (12)
C8	0.0481 (13)	0.0364 (13)	0.0460 (14)	0.0004 (11)	0.0182 (11)	−0.0058 (11)
C9	0.0388 (13)	0.0496 (15)	0.0589 (16)	−0.0048 (11)	0.0208 (12)	−0.0046 (12)
C10	0.0404 (14)	0.0505 (15)	0.0444 (14)	−0.0067 (11)	0.0073 (11)	−0.0089 (12)
C11	0.0361 (12)	0.0393 (12)	0.0385 (13)	0.0011 (10)	0.0082 (10)	0.0019 (10)
C12	0.0420 (13)	0.0527 (16)	0.0577 (16)	−0.0122 (11)	0.0184 (12)	−0.0070 (13)
C13	0.0523 (15)	0.0526 (15)	0.0522 (16)	−0.0137 (13)	0.0113 (12)	−0.0185 (13)
C14	0.0430 (14)	0.0505 (14)	0.0399 (14)	−0.0006 (11)	0.0096 (11)	0.0036 (12)
C15	0.0530 (15)	0.0543 (16)	0.0514 (16)	0.0030 (13)	0.0138 (12)	0.0071 (13)
C16	0.0502 (15)	0.0646 (18)	0.0593 (17)	0.0085 (13)	0.0258 (13)	−0.0005 (14)
C17	0.0615 (17)	0.0599 (16)	0.0464 (15)	−0.0071 (13)	0.0230 (13)	0.0016 (13)
C18	0.0544 (16)	0.0455 (14)	0.0484 (15)	−0.0047 (12)	0.0061 (13)	−0.0015 (12)
C19	0.0424 (13)	0.0543 (15)	0.0569 (16)	0.0007 (12)	0.0177 (12)	−0.0100 (13)
C20	0.083 (2)	0.0598 (19)	0.077 (2)	0.0045 (16)	0.0011 (18)	0.0119 (17)
N1	0.0487 (12)	0.0481 (12)	0.0385 (12)	0.0018 (10)	0.0166 (10)	0.0028 (10)
N2	0.0739 (16)	0.0456 (13)	0.0613 (15)	−0.0030 (12)	0.0324 (14)	−0.0110 (12)
N3	0.0509 (12)	0.0561 (13)	0.0435 (12)	−0.0055 (10)	0.0215 (10)	0.0003 (10)
O1	0.0639 (12)	0.0816 (14)	0.0614 (13)	−0.0203 (11)	0.0363 (11)	−0.0123 (11)
O2	0.0681 (12)	0.1012 (17)	0.0398 (10)	−0.0139 (12)	0.0165 (9)	−0.0199 (11)
O3	0.0610 (12)	0.1101 (18)	0.0415 (11)	−0.0010 (12)	0.0172 (10)	−0.0187 (11)
O4	0.0703 (13)	0.1145 (19)	0.0523 (12)	−0.0193 (13)	0.0329 (10)	0.0023 (12)
O5	0.0611 (12)	0.0994 (17)	0.0672 (13)	−0.0230 (12)	0.0319 (11)	−0.0106 (12)
O6	0.0611 (12)	0.0730 (12)	0.0448 (11)	−0.0093 (10)	0.0192 (9)	−0.0126 (10)
O7	0.1097 (18)	0.0930 (18)	0.0665 (14)	−0.0288 (15)	0.0356 (13)	−0.0336 (14)
O8	0.0901 (17)	0.0946 (17)	0.0888 (17)	−0.0178 (14)	0.0592 (14)	−0.0217 (14)

Geometric parameters (Å, º) top

C1—C2	1.372 (3)	C12—H12	0.9300
C1—C6	1.373 (3)	C13—H13	0.9300
C1—C7	1.514 (3)	C14—O5	1.201 (3)
C2—C3	1.381 (3)	C14—O6	1.306 (3)
C2—H2	0.9300	C15—N3	1.320 (3)
C3—C4	1.366 (3)	C15—C16	1.369 (4)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.367 (3)	C16—C17	1.368 (4)
C4—N1	1.472 (3)	C16—H16	0.9300
C5—C6	1.383 (3)	C17—C18	1.375 (4)
C5—H5	0.9300	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.370 (4)
C7—O4	1.236 (3)	C18—C20	1.496 (4)
C7—O3	1.240 (3)	C19—N3	1.329 (4)
C8—C9	1.369 (3)	C19—H19	0.9300
C8—C13	1.372 (3)	C20—H20A	0.9600
C8—N2	1.474 (3)	C20—H20B	0.9600
C9—C10	1.374 (3)	C20—H20C	0.9600
C9—H9	0.9300	N1—O2	1.210 (3)
C10—C11	1.380 (3)	N1—O1	1.213 (2)
C10—H10	0.9300	N2—O8	1.208 (3)
C11—C12	1.375 (3)	N2—O7	1.214 (3)
C11—C14	1.492 (3)	N3—H3A	0.88 (2)
C12—C13	1.377 (4)	O6—H6A	0.82 (2)

C2—C1—C6	119.6 (2)	C8—C13—H13	120.7
C2—C1—C7	120.0 (2)	C12—C13—H13	120.7
C6—C1—C7	120.3 (2)	O5—C14—O6	124.2 (2)
C1—C2—C3	120.4 (2)	O5—C14—C11	122.8 (2)
C1—C2—H2	119.8	O6—C14—C11	113.0 (2)
C3—C2—H2	119.8	N3—C15—C16	119.6 (3)
C4—C3—C2	118.6 (2)	N3—C15—H15	120.2
C4—C3—H3	120.7	C16—C15—H15	120.2
C2—C3—H3	120.7	C17—C16—C15	118.8 (2)
C3—C4—C5	122.6 (2)	C17—C16—H16	120.6
C3—C4—N1	119.1 (2)	C15—C16—H16	120.6
C5—C4—N1	118.38 (19)	C16—C17—C18	121.3 (2)
C4—C5—C6	117.9 (2)	C16—C17—H17	119.3
C4—C5—H5	121.1	C18—C17—H17	119.3
C6—C5—H5	121.1	C19—C18—C17	116.8 (2)
C1—C6—C5	120.9 (2)	C19—C18—C20	120.6 (3)
C1—C6—H6	119.5	C17—C18—C20	122.6 (3)
C5—C6—H6	119.5	N3—C19—C18	121.2 (2)
O4—C7—O3	126.2 (2)	N3—C19—H19	119.4
O4—C7—C1	117.1 (2)	C18—C19—H19	119.4
O3—C7—C1	116.7 (2)	C18—C20—H20A	109.5
C9—C8—C13	122.0 (2)	C18—C20—H20B	109.5
C9—C8—N2	118.6 (2)	H20A—C20—H20B	109.5
C13—C8—N2	119.3 (2)	C18—C20—H20C	109.5
C8—C9—C10	118.6 (2)	H20A—C20—H20C	109.5
C8—C9—H9	120.7	H20B—C20—H20C	109.5
C10—C9—H9	120.7	O2—N1—O1	123.6 (2)
C9—C10—C11	120.8 (2)	O2—N1—C4	118.11 (19)
C9—C10—H10	119.6	O1—N1—C4	118.2 (2)
C11—C10—H10	119.6	O8—N2—O7	123.3 (2)
C12—C11—C10	119.2 (2)	O8—N2—C8	118.7 (2)
C12—C11—C14	118.7 (2)	O7—N2—C8	118.0 (2)
C10—C11—C14	122.0 (2)	C15—N3—C19	122.2 (2)
C11—C12—C13	120.7 (2)	C15—N3—H3A	119.7 (19)
C11—C12—H12	119.6	C19—N3—H3A	118.2 (19)
C13—C12—H12	119.6	C14—O6—H6A	112 (3)
C8—C13—C12	118.6 (2)

C6—C1—C2—C3	0.2 (4)	N2—C8—C13—C12	177.4 (2)
C7—C1—C2—C3	−178.2 (2)	C11—C12—C13—C8	−1.2 (4)
C1—C2—C3—C4	0.3 (4)	C12—C11—C14—O5	−2.0 (4)
C2—C3—C4—C5	−0.8 (4)	C10—C11—C14—O5	179.5 (3)
C2—C3—C4—N1	178.5 (2)	C12—C11—C14—O6	177.2 (2)
C3—C4—C5—C6	0.7 (4)	C10—C11—C14—O6	−1.3 (3)
N1—C4—C5—C6	−178.7 (2)	N3—C15—C16—C17	0.2 (4)
C2—C1—C6—C5	−0.4 (4)	C15—C16—C17—C18	−0.1 (4)
C7—C1—C6—C5	178.1 (2)	C16—C17—C18—C19	−0.3 (4)
C4—C5—C6—C1	−0.1 (4)	C16—C17—C18—C20	179.8 (3)
C2—C1—C7—O4	5.9 (4)	C17—C18—C19—N3	0.5 (4)
C6—C1—C7—O4	−172.5 (3)	C20—C18—C19—N3	−179.5 (2)
C2—C1—C7—O3	−174.2 (2)	C3—C4—N1—O2	1.3 (3)
C6—C1—C7—O3	7.4 (4)	C5—C4—N1—O2	−179.4 (2)
C13—C8—C9—C10	0.9 (4)	C3—C4—N1—O1	−178.8 (2)
N2—C8—C9—C10	−176.9 (2)	C5—C4—N1—O1	0.6 (3)
C8—C9—C10—C11	0.2 (4)	C9—C8—N2—O8	−3.3 (4)
C9—C10—C11—C12	−1.8 (4)	C13—C8—N2—O8	178.9 (3)
C9—C10—C11—C14	176.7 (2)	C9—C8—N2—O7	177.2 (3)
C10—C11—C12—C13	2.3 (4)	C13—C8—N2—O7	−0.6 (4)
C14—C11—C12—C13	−176.2 (2)	C16—C15—N3—C19	0.0 (4)
C9—C8—C13—C12	−0.4 (4)	C18—C19—N3—C15	−0.4 (4)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the ring (C1-C6)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O4	0.88 (2)	1.73 (2)	2.612 (3)	175 (3)
O6—H6A···O3	0.83 (2)	1.70 (2)	2.518 (2)	175 (4)
C9—H9···O1ⁱ	0.93	2.47	3.271 (3)	144
C15—H15···O3ⁱⁱ	0.93	2.41	3.218 (3)	145
C16—H16···O2ⁱ	0.93	2.59	3.353 (3)	140
C19—H19···O5ⁱⁱⁱ	0.93	2.42	3.293 (3)	156
C13—H13···Cg2^iv	0.93	2.83	3.564 (3)	137

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

Acknowledgements

The authors acknowledge the SAIF, IIT, Madras, for the data collection.

References

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Volume 1| Part 6| June 2016| x160979

doi:10.1107/S2414314616009792

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-Methyl­pyridinium 4-nitro­benzoate–4-nitro­benzoic acid (1/1)

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

3-Methylpyridinium 4-nitrobenzoate–4-nitrobenzoic acid (1/1)