Bis(2-amino-6-methyl­pyridinium) 3-nitro­benzene-1,2-di­carboxyl­ate

Sivakumar, P.; Sudhahar, S.; Israel, S.; Chakkaravarthi, G.

doi:10.1107/S2414314616012335

organic compounds

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ISSN: 2414-3146

Volume 1| Part 8| August 2016| x161233

doi:10.1107/S2414314616012335

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Bis(2-amino-6-methylpyridinium) 3-nitrobenzene-1,2-dicarboxylate

P. Sivakumar,^a,^b S. Sudhahar,^c S. Israel ^d ^* and G. Chakkaravarthi ^b ^*

^aResearch and Development Centre, Bharathiar University, Coimbatore 641 046, India, ^bDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, ^cDepartment of Physics, Alagappa University, Karaikkudi 630 003, India, and ^dPost 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 26 July 2016; accepted 29 July 2016; online 5 August 2016)

In the title molecular salt, 2C₆H₉N₂⁺·C₈H₃NO₆²⁻, the cations are protonated at their pyridine N atoms. The cations and anion are linked by N—H⋯O and C—H⋯O hydrogen bonds and a π–π interaction [centroid-to-centroid distance = 3.7299 (13) Å]. In the crystal, N—H⋯O hydrogen bonds link the anions and cations into an infinite two-dimensional network parallel to (10-1). N—H⋯O hydrogen bonds generate R₁²(4), R₂¹(6), R₂⁴(18) and R₂²(11) ring motifs. The structure also features weak C—H⋯O and C—H⋯π interactions, which lead to the formation of a three-dimensional network.

Keywords: molecular salt; crystal structure; hydrogen bonding.

CCDC reference: 1496855

Structure description

Pyridine derivatives are known to exhibit pharmacological properties such as antiproliferative, antitubolin (Magedov et al., 2008 ) and antiviral (Hamdouchi et al., 1999 ) activities. We report herein the synthesis and the crystal structure of the title molecular salt (Fig. 1). The geometric parameters are in agreement with reported similar structures (Sivakumar et al., 2016a ,b ). The asymmetric unit contains two 2-amino-6-methylpyridinium cations and one 3-nitrobenzene-1,2-dicarboxylate anion. The cations are protonated at its pyridine N (N2 and N4) atoms and the anion is deprotonated at hydroxy O (O4 and O6) atoms. The cations and anion are linked by N—H⋯O and C—H⋯O hydrogen bonds (Table 1) and a π–π interaction [Cg2⋯Cg3 = 3.7299 (13) Å; Cg2 and Cg3 are the centroids of the rings (N2/C9–C13) and (N4/C15–C19), respectively].

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O5ⁱ	0.87 (2)	1.93 (2)	2.777 (2)	167 (2)
N2—H2A⋯O6ⁱ	0.87 (2)	2.69 (2)	3.364 (2)	136 (2)
N3—H3A⋯O6ⁱ	0.86	1.91	2.755 (2)	167
N3—H3B⋯O4	0.86	1.97	2.825 (2)	171
N4—H4A⋯O3ⁱⁱ	0.87 (2)	1.81 (2)	2.678 (2)	171 (2)
N5—H5A⋯O5ⁱⁱ	0.86	2.16	2.949 (2)	152
N5—H5B⋯O3ⁱ	0.86	2.17	2.993 (2)	161
C17—H17⋯O6	0.93	2.33	3.241 (3)	166
C18—H18⋯O4ⁱ	0.93	2.42	3.293 (2)	156
C14—H14C⋯Cg1ⁱⁱⁱ	0.96	2.73	3.490 (2)	137
Symmetry codes: (i) -x+2, -y, -z+1; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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

In the crystal, N4—H4A⋯O3ⁱⁱ and N5—H5A⋯O5ⁱⁱ hydrogen bonds (Table 1, Fig. 2) generate an R₂²(11) ring-motif enclosing the atoms (N5/H5A/O5/C8/C3/C2/C7/O3/H4A/N4/C19). The N2—H2A⋯O5ⁱ and N3—H3A⋯O6ⁱ hydrogen bonds (Table 1, Fig. 2) generate a bifurcated R₁²(4) ring-motif, constituted by the atoms (C8/O5/H2A/O6). The N2—H2A⋯O6ⁱ and N3—H3A⋯O6ⁱ (Table 1, Fig. 2) hydrogen bonds generate a bifurcated R₂¹(6) ring-motif, constituted by the atoms (C13/N2/H2A/O6/H3A/N3). A pair of N3—H3B⋯O4 and N3—H3A⋯O6ⁱ hydrogen bonds generate an R₂⁴(18) ring-motif (Table 1, Fig. 2). The N—H⋯O hydrogen bonds link the components into an infinite two-dimensional network parallel to the (10 $[\overline{1}]$ ) plane. A weak C—H⋯O hydrogen bond and a C—H⋯π interaction (Table 1) lead to the formation of a three dimensional network (Fig. 3).

Figure 2
A partial view of the crystal packing of the title molecular salt, showing the ring graph-set motifs. H atoms not involving in hydrogen bonds have been omitted for clarity.

Figure 3
The crystal packing of the title molecular salt viewed along the b axis. Hydrogen bonds are shown as dashed lines. H atoms not involving in hydrogen bonds have been omitted for clarity.

Synthesis and crystallization

The title molecular salt was synthesized using the raw materials 3-nitrophthalic acid (2.11 g) and 2-amino-6-methylpyridine (1.08 g) in an equimolar ratio. These reactants were dissolved in 20 ml of methanol and kept for slow evaporation at room temperature. After a span of 30 days, 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	2C₆H₉N₂⁺·C₈H₃NO₆²⁻
M_r	427.42
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	13.5461 (15), 7.7453 (9), 19.625 (2)
β (°)	101.486 (4)
V (Å³)	2017.8 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.11
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004 )
T_min, T_max	0.975, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	28851, 3776, 2886
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.123, 1.03
No. of reflections	3776
No. of parameters	290
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.21
Computer programs: APEX2 and SAINT (Bruker, 2004), SHELXS97 and SHELXL97 (Sheldrick, 2008 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1496855

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2414314616012335/vm4013sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616012335/vm4013Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616012335/vm4013Isup3.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).

Bis(2-amino-6-methylpyridinium) 3-nitrobenzene-1,2-dicarboxylate top

Crystal data top

2C₆H₉N₂⁺·C₈H₃NO₆²⁻	F(000) = 896
M_r = 427.42	D_x = 1.407 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9996 reflections
a = 13.5461 (15) Å	θ = 2.8–25.2°
b = 7.7453 (9) Å	µ = 0.11 mm⁻¹
c = 19.625 (2) Å	T = 295 K
β = 101.486 (4)°	Block, colourless
V = 2017.8 (4) Å³	0.24 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3776 independent reflections
Radiation source: fine-focus sealed tube	2886 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω and φ scan	θ_max = 25.6°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −16→16
T_min = 0.975, T_max = 0.981	k = −9→9
28851 measured reflections	l = −23→23

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0576P)² + 0.8038P] where P = (F_o² + 2F_c²)/3
3776 reflections	(Δ/σ)_max < 0.001
290 parameters	Δρ_max = 0.22 e Å⁻³
2 restraints	Δρ_min = −0.21 e Å⁻³

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	1.09358 (13)	0.1082 (3)	0.22870 (9)	0.0375 (4)
C2	1.02798 (12)	0.0628 (2)	0.27184 (8)	0.0295 (4)
C3	1.00168 (13)	0.1935 (2)	0.31418 (9)	0.0328 (4)
C4	1.04193 (15)	0.3587 (3)	0.31251 (11)	0.0431 (5)
H4	1.0247	0.4441	0.3414	0.052*
C5	1.10690 (16)	0.3976 (3)	0.26877 (12)	0.0543 (6)
H5	1.1331	0.5084	0.2683	0.065*
C6	1.13264 (15)	0.2732 (3)	0.22620 (11)	0.0509 (6)
H6	1.1756	0.2986	0.1961	0.061*
C7	0.98915 (13)	−0.1210 (2)	0.27654 (8)	0.0305 (4)
C8	0.93033 (14)	0.1621 (2)	0.36309 (9)	0.0352 (4)
C9	1.33900 (14)	0.0667 (3)	0.57066 (10)	0.0398 (4)
C10	1.39045 (17)	0.1214 (3)	0.52207 (12)	0.0532 (6)
H10	1.4536	0.1721	0.5355	0.064*
C11	1.34777 (19)	0.1009 (3)	0.45176 (12)	0.0602 (6)
H11	1.3827	0.1396	0.4184	0.072*
C12	1.25659 (18)	0.0259 (3)	0.43120 (11)	0.0546 (6)
H12	1.2290	0.0133	0.3841	0.066*
C13	1.20386 (15)	−0.0330 (3)	0.48160 (10)	0.0409 (5)
C14	1.37628 (16)	0.0794 (3)	0.64726 (11)	0.0502 (5)
H14A	1.4015	−0.0309	0.6651	0.075*
H14B	1.3220	0.1138	0.6691	0.075*
H14C	1.4293	0.1634	0.6569	0.075*
C15	1.30217 (14)	0.5431 (2)	0.55806 (10)	0.0381 (4)
C16	1.22798 (16)	0.4884 (3)	0.50592 (10)	0.0457 (5)
H16	1.2320	0.5088	0.4598	0.055*
C17	1.14507 (16)	0.4010 (3)	0.52183 (11)	0.0481 (5)
H17	1.0938	0.3637	0.4860	0.058*
C18	1.13860 (14)	0.3698 (3)	0.58871 (10)	0.0434 (5)
H18	1.0841	0.3089	0.5987	0.052*
C19	1.21448 (14)	0.4300 (2)	0.64267 (10)	0.0365 (4)
C20	1.39675 (16)	0.6288 (3)	0.54851 (11)	0.0506 (5)
H20A	1.4491	0.5441	0.5513	0.076*
H20B	1.4163	0.7138	0.5843	0.076*
H20C	1.3858	0.6839	0.5038	0.076*
N1	1.12444 (13)	−0.0224 (3)	0.18282 (9)	0.0506 (5)
N2	1.24708 (11)	−0.0084 (2)	0.54935 (8)	0.0363 (4)
N3	1.11547 (13)	−0.1094 (3)	0.46649 (9)	0.0535 (5)
H3A	1.0863	−0.1428	0.4993	0.064*
H3B	1.0869	−0.1261	0.4238	0.064*
N4	1.29323 (11)	0.5142 (2)	0.62538 (8)	0.0351 (4)
N5	1.21327 (13)	0.4063 (2)	0.70948 (8)	0.0500 (5)
H5A	1.2620	0.4443	0.7408	0.060*
H5B	1.1637	0.3529	0.7214	0.060*
O1	1.14462 (17)	0.0271 (3)	0.12823 (10)	0.0919 (7)
O2	1.12823 (14)	−0.1731 (2)	0.20011 (9)	0.0686 (5)
O3	0.92072 (9)	−0.17215 (17)	0.22829 (6)	0.0407 (3)
O4	1.02835 (10)	−0.20448 (17)	0.32863 (6)	0.0435 (3)
O5	0.85596 (10)	0.0646 (2)	0.34366 (7)	0.0478 (4)
O6	0.94974 (12)	0.2387 (2)	0.41937 (8)	0.0608 (4)
H2A	1.2139 (14)	−0.042 (3)	0.5804 (9)	0.051 (6)*
H4A	1.3394 (12)	0.558 (2)	0.6583 (8)	0.040 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0335 (9)	0.0455 (12)	0.0344 (10)	−0.0022 (8)	0.0091 (8)	0.0049 (8)
C2	0.0290 (8)	0.0322 (9)	0.0268 (8)	−0.0004 (7)	0.0045 (7)	0.0027 (7)
C3	0.0322 (9)	0.0325 (10)	0.0322 (9)	−0.0023 (7)	0.0032 (7)	−0.0001 (7)
C4	0.0443 (11)	0.0329 (10)	0.0501 (11)	−0.0038 (9)	0.0042 (9)	−0.0015 (9)
C5	0.0528 (13)	0.0401 (12)	0.0675 (15)	−0.0170 (10)	0.0057 (11)	0.0095 (11)
C6	0.0429 (11)	0.0609 (15)	0.0504 (12)	−0.0138 (10)	0.0128 (9)	0.0143 (11)
C7	0.0356 (9)	0.0317 (10)	0.0258 (8)	0.0019 (7)	0.0099 (7)	−0.0020 (7)
C8	0.0389 (10)	0.0353 (10)	0.0321 (9)	0.0036 (8)	0.0091 (8)	−0.0033 (8)
C9	0.0400 (10)	0.0340 (10)	0.0464 (11)	0.0029 (8)	0.0108 (8)	0.0027 (8)
C10	0.0491 (12)	0.0514 (13)	0.0623 (14)	−0.0040 (10)	0.0189 (10)	0.0130 (11)
C11	0.0681 (15)	0.0644 (16)	0.0561 (14)	0.0038 (13)	0.0315 (12)	0.0158 (12)
C12	0.0674 (15)	0.0641 (15)	0.0352 (11)	0.0118 (12)	0.0173 (10)	0.0067 (10)
C13	0.0446 (11)	0.0427 (11)	0.0352 (10)	0.0091 (9)	0.0076 (8)	0.0007 (8)
C14	0.0468 (12)	0.0522 (13)	0.0484 (12)	−0.0062 (10)	0.0021 (9)	−0.0003 (10)
C15	0.0446 (10)	0.0344 (10)	0.0382 (10)	0.0049 (8)	0.0154 (8)	0.0004 (8)
C16	0.0551 (12)	0.0496 (13)	0.0334 (10)	0.0020 (10)	0.0113 (9)	−0.0010 (9)
C17	0.0480 (12)	0.0503 (13)	0.0435 (11)	−0.0025 (10)	0.0030 (9)	−0.0076 (9)
C18	0.0396 (10)	0.0422 (12)	0.0497 (12)	−0.0069 (9)	0.0119 (9)	−0.0049 (9)
C19	0.0394 (10)	0.0327 (10)	0.0398 (10)	0.0017 (8)	0.0133 (8)	−0.0012 (8)
C20	0.0509 (12)	0.0539 (13)	0.0531 (12)	−0.0025 (10)	0.0245 (10)	0.0013 (10)
N1	0.0440 (10)	0.0715 (14)	0.0413 (10)	−0.0031 (9)	0.0202 (8)	−0.0031 (9)
N2	0.0375 (8)	0.0402 (9)	0.0328 (8)	0.0024 (7)	0.0110 (7)	0.0012 (7)
N3	0.0526 (11)	0.0705 (13)	0.0353 (9)	−0.0023 (9)	0.0033 (8)	−0.0034 (8)
N4	0.0357 (8)	0.0357 (9)	0.0349 (8)	−0.0020 (7)	0.0094 (7)	−0.0019 (7)
N5	0.0504 (10)	0.0634 (12)	0.0387 (9)	−0.0143 (9)	0.0148 (8)	0.0005 (8)
O1	0.1245 (17)	0.1093 (17)	0.0595 (11)	−0.0101 (13)	0.0608 (12)	0.0005 (11)
O2	0.0831 (12)	0.0595 (12)	0.0740 (11)	0.0119 (9)	0.0418 (9)	−0.0062 (9)
O3	0.0436 (7)	0.0376 (8)	0.0384 (7)	−0.0055 (6)	0.0020 (6)	−0.0036 (6)
O4	0.0609 (9)	0.0361 (8)	0.0319 (7)	0.0006 (6)	0.0056 (6)	0.0037 (6)
O5	0.0398 (7)	0.0659 (10)	0.0404 (7)	−0.0131 (7)	0.0146 (6)	−0.0116 (7)
O6	0.0758 (11)	0.0668 (11)	0.0441 (8)	−0.0194 (9)	0.0221 (8)	−0.0228 (8)

Geometric parameters (Å, º) top

C1—C6	1.388 (3)	C13—N2	1.355 (2)
C1—C2	1.389 (2)	C14—H14A	0.9600
C1—N1	1.470 (3)	C14—H14B	0.9600
C2—C3	1.400 (2)	C14—H14C	0.9600
C2—C7	1.526 (3)	C15—C16	1.352 (3)
C3—C4	1.393 (3)	C15—N4	1.369 (2)
C3—C8	1.511 (2)	C15—C20	1.488 (3)
C4—C5	1.380 (3)	C16—C17	1.399 (3)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.365 (3)	C17—C18	1.354 (3)
C5—H5	0.9300	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.401 (3)
C7—O4	1.237 (2)	C18—H18	0.9300
C7—O3	1.250 (2)	C19—N5	1.327 (2)
C8—O6	1.235 (2)	C19—N4	1.350 (2)
C8—O5	1.256 (2)	C20—H20A	0.9600
C9—C10	1.356 (3)	C20—H20B	0.9600
C9—N2	1.363 (2)	C20—H20C	0.9600
C9—C14	1.491 (3)	N1—O2	1.213 (3)
C10—C11	1.395 (3)	N1—O1	1.219 (2)
C10—H10	0.9300	N2—H2A	0.867 (10)
C11—C12	1.352 (3)	N3—H3A	0.8600
C11—H11	0.9300	N3—H3B	0.8600
C12—C13	1.406 (3)	N4—H4A	0.874 (9)
C12—H12	0.9300	N5—H5A	0.8600
C13—N3	1.316 (3)	N5—H5B	0.8600

C6—C1—C2	123.34 (19)	H14A—C14—H14B	109.5
C6—C1—N1	117.10 (17)	C9—C14—H14C	109.5
C2—C1—N1	119.57 (17)	H14A—C14—H14C	109.5
C1—C2—C3	116.58 (17)	H14B—C14—H14C	109.5
C1—C2—C7	122.89 (16)	C16—C15—N4	118.96 (18)
C3—C2—C7	120.47 (15)	C16—C15—C20	125.00 (18)
C4—C3—C2	120.20 (17)	N4—C15—C20	116.00 (17)
C4—C3—C8	117.76 (17)	C15—C16—C17	119.44 (18)
C2—C3—C8	122.04 (16)	C15—C16—H16	120.3
C5—C4—C3	121.1 (2)	C17—C16—H16	120.3
C5—C4—H4	119.5	C18—C17—C16	120.82 (19)
C3—C4—H4	119.5	C18—C17—H17	119.6
C6—C5—C4	119.9 (2)	C16—C17—H17	119.6
C6—C5—H5	120.0	C17—C18—C19	119.61 (19)
C4—C5—H5	120.0	C17—C18—H18	120.2
C5—C6—C1	118.85 (19)	C19—C18—H18	120.2
C5—C6—H6	120.6	N5—C19—N4	118.74 (17)
C1—C6—H6	120.6	N5—C19—C18	123.33 (18)
O4—C7—O3	126.30 (17)	N4—C19—C18	117.92 (17)
O4—C7—C2	116.17 (15)	C15—C20—H20A	109.5
O3—C7—C2	117.52 (15)	C15—C20—H20B	109.5
O6—C8—O5	125.12 (17)	H20A—C20—H20B	109.5
O6—C8—C3	116.18 (17)	C15—C20—H20C	109.5
O5—C8—C3	118.68 (15)	H20A—C20—H20C	109.5
C10—C9—N2	118.93 (19)	H20B—C20—H20C	109.5
C10—C9—C14	124.77 (19)	O2—N1—O1	123.0 (2)
N2—C9—C14	116.29 (17)	O2—N1—C1	119.49 (17)
C9—C10—C11	119.4 (2)	O1—N1—C1	117.6 (2)
C9—C10—H10	120.3	C13—N2—C9	123.43 (17)
C11—C10—H10	120.3	C13—N2—H2A	117.6 (15)
C12—C11—C10	121.2 (2)	C9—N2—H2A	119.0 (15)
C12—C11—H11	119.4	C13—N3—H3A	120.0
C10—C11—H11	119.4	C13—N3—H3B	120.0
C11—C12—C13	119.4 (2)	H3A—N3—H3B	120.0
C11—C12—H12	120.3	C19—N4—C15	123.21 (16)
C13—C12—H12	120.3	C19—N4—H4A	119.1 (13)
N3—C13—N2	118.70 (18)	C15—N4—H4A	117.6 (13)
N3—C13—C12	123.66 (19)	C19—N5—H5A	120.0
N2—C13—C12	117.64 (19)	C19—N5—H5B	120.0
C9—C14—H14A	109.5	H5A—N5—H5B	120.0
C9—C14—H14B	109.5

C6—C1—C2—C3	0.0 (3)	C14—C9—C10—C11	179.4 (2)
N1—C1—C2—C3	−179.99 (15)	C9—C10—C11—C12	−0.7 (4)
C6—C1—C2—C7	−177.19 (17)	C10—C11—C12—C13	−0.1 (4)
N1—C1—C2—C7	2.8 (3)	C11—C12—C13—N3	−179.1 (2)
C1—C2—C3—C4	−0.9 (2)	C11—C12—C13—N2	1.1 (3)
C7—C2—C3—C4	176.34 (16)	N4—C15—C16—C17	−1.2 (3)
C1—C2—C3—C8	179.48 (15)	C20—C15—C16—C17	176.5 (2)
C7—C2—C3—C8	−3.3 (2)	C15—C16—C17—C18	−0.3 (3)
C2—C3—C4—C5	0.9 (3)	C16—C17—C18—C19	1.7 (3)
C8—C3—C4—C5	−179.45 (17)	C17—C18—C19—N5	179.3 (2)
C3—C4—C5—C6	0.0 (3)	C17—C18—C19—N4	−1.5 (3)
C4—C5—C6—C1	−0.9 (3)	C6—C1—N1—O2	150.7 (2)
C2—C1—C6—C5	0.9 (3)	C2—C1—N1—O2	−29.3 (3)
N1—C1—C6—C5	−179.07 (18)	C6—C1—N1—O1	−29.7 (3)
C1—C2—C7—O4	103.5 (2)	C2—C1—N1—O1	150.3 (2)
C3—C2—C7—O4	−73.6 (2)	N3—C13—N2—C9	178.91 (18)
C1—C2—C7—O3	−77.2 (2)	C12—C13—N2—C9	−1.3 (3)
C3—C2—C7—O3	105.67 (19)	C10—C9—N2—C13	0.4 (3)
C4—C3—C8—O6	−36.3 (2)	C14—C9—N2—C13	−178.47 (18)
C2—C3—C8—O6	143.32 (19)	N5—C19—N4—C15	179.10 (18)
C4—C3—C8—O5	142.41 (18)	C18—C19—N4—C15	−0.1 (3)
C2—C3—C8—O5	−38.0 (3)	C16—C15—N4—C19	1.5 (3)
N2—C9—C10—C11	0.6 (3)	C20—C15—N4—C19	−176.50 (18)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5ⁱ	0.87 (2)	1.93 (2)	2.777 (2)	167 (2)
N2—H2A···O6ⁱ	0.87 (2)	2.69 (2)	3.364 (2)	136 (2)
N3—H3A···O6ⁱ	0.86	1.91	2.755 (2)	167
N3—H3B···O4	0.86	1.97	2.825 (2)	171
N4—H4A···O3ⁱⁱ	0.87 (2)	1.81 (2)	2.678 (2)	171 (2)
N5—H5A···O5ⁱⁱ	0.86	2.16	2.949 (2)	152
N5—H5B···O3ⁱ	0.86	2.17	2.993 (2)	161
C17—H17···O6	0.93	2.33	3.241 (3)	166
C18—H18···O4ⁱ	0.93	2.42	3.293 (2)	156
C14—H14C···Cg1ⁱⁱⁱ	0.96	2.73	3.490 (2)	137

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

Acknowledgements

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

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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IUCrDATA

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Volume 1| Part 8| August 2016| x161233

doi:10.1107/S2414314616012335

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

Bis(2-amino-6-methyl­pyridinium) 3-nitro­benzene-1,2-di­carboxyl­ate

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

Bis(2-amino-6-methylpyridinium) 3-nitrobenzene-1,2-dicarboxylate