2-Amino-3-carb­oxy­pyridinium perchlorate

Berrah, F.; Bouacida, S.; Anana, H.; Roisnel, T.

doi:10.1107/S1600536812018922

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1601-o1602

doi:10.1107/S1600536812018922

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2-Amino-3-carboxypyridinium perchlorate

Fadila Berrah,^a ^* Sofiane Bouacida,^b Hayet Anana ^a and Thierry Roisnel ^c

^aLaboratoire de Chimie Appliquée et Technologie des Matériaux (LCATM), Université d'Oum El Bouaghi 04000, Algeria, ^bUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Université Mentouri Constantine 25000, Algeria, and ^cCentre de Difractométrie X, UMR 6226 CNRS Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France
^*Correspondence e-mail: fadilaber@yahoo.fr

(Received 11 April 2012; accepted 26 April 2012; online 2 May 2012)

The asymmetric unit includes two crystallographically independent equivalents of the title salt, C₆H₇N₂O₂⁺·ClO₄⁻. The cations and anions form separate layers alternating along the c axis, which are linked by N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds into a two-dimensional network parallel to (100). Further C—H⋯O contacts connect these layers, forming a three-dimensional network, in which R₄⁴(20) rings and C₂²(11) infinite chains can be identified.

Related literature

For structural studies of hybrid compounds of 2-aminonicotinic acid, see: Akriche & Rzaigui (2007 ); Berrah et al. (2011a ,b ). For related perchlorate compounds, see: Toumi Akriche et al. (2010 ); Bendjeddou et al. (2003 ). For hydrogen-bond motifs, see: Etter et al. (1990 ); Grell et al. (1999 ).

Experimental

Crystal data

C₆H₇N₂O₂⁺·ClO₄⁻
M_r = 238.59
Monoclinic, P 2/c
a = 17.3573 (12) Å
b = 5.0800 (4) Å
c = 21.6293 (17) Å
β = 107.239 (2)°
V = 1821.5 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 150 K
0.48 × 0.17 × 0.08 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ) T_min = 0.847, T_max = 0.966
13822 measured reflections
4142 independent reflections
3305 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.110
S = 1.11
4142 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯O21	0.82	1.99	2.810 (3)	173
O1B—H1B⋯O42	0.82	1.96	2.779 (3)	176
N2A—H2A⋯O32	0.86	2.24	2.968 (3)	142
N2B—H2B⋯O31	0.86	2.31	3.005 (3)	138
N2B—H2B⋯O22ⁱ	0.86	2.34	2.992 (3)	133
N1A—H11A⋯O22ⁱⁱ	0.86	2.50	3.211 (3)	141
N1A—H11A⋯O32	0.86	2.58	3.231 (3)	133
N1B—H11B⋯O31	0.86	2.32	3.000 (3)	136
N1B—H11B⋯O41ⁱⁱⁱ	0.86	2.54	3.268 (3)	143
N1A—H12A⋯O2Bⁱⁱ	0.86	2.19	2.928 (3)	144
N1B—H12B⋯O2Aⁱⁱⁱ	0.86	2.22	2.971 (3)	145
C4A—H4A⋯O11^iv	0.93	2.57	3.312 (3)	137
C4B—H4B⋯O32^v	0.93	2.53	3.433 (3)	165
C5A—H5A⋯O11^vi	0.93	2.37	3.277 (3)	164
C5B—H5B⋯O12^vii	0.93	2.52	3.450 (3)	177
Symmetry codes: (i) $[x, -y, z+{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) x, y-1, z; (iv) $[x, -y, z-{\script{1\over 2}}]$ ; (v) $[x, -y+1, z+{\script{1\over 2}}]$ ; (vi) $[-x+1, y-1, -z+{\script{1\over 2}}]$ ; (vii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812018922/ld2056sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812018922/ld2056Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812018922/ld2056Isup3.cml

checkCIF report

Comment top

As a continuation of the systematic studies on synthesis and structural characterization of the products of derivatives of nicotinic acid with inorganic acids, and as an attempt to establish a relationship between the nature of the anion and the resulting hydrogen-bonding pattern, we report here the crystal structure of the title compound obtained by reaction between 2-aminonicotinic and perchloric acids. Related compounds obtained with dihydrogen phosphate, sulfate and nitrate anions, have been reported previously (Akriche & Rzaigui 2007; Berrah et al. 2011a,b).

The dimers of 2-aminonicotinium cations are formed via N—H···O h-bonds (NH of the amine group with the O of the carboxylic group). Similar dimers have been also observed in the structures with dihydrogen phosphate and sulfate anions (Akriche & Rzaigui 2007; Berrah et al. 2011a), while cations in the nitrate structure adopt a different configuration (Berrah et al. 2011b).

In the crystal structure, cationic and anionic layers alternate along the c axis and are linked by intermolecular N—H···O, O—H···O and weak C—H···O hydrogen bonds (see table 1) resulting in a two-dimensional network parallel to (100) (Fig.2). Further C—H···O contacts connect these layers, forming a three-dimensional network in which R₄⁴(20) rings and C₂²(11) infinite chains are generated (Etter et al. 1990; Grell et al. 1999).

Related literature top

For structural studies of hybrid compounds of 2-aminonicotinic acid, see: Akriche & Rzaigui (2007); Berrah et al. (2011a,b). For related perchlorate compounds, see: Toumi Akriche et al. (2010); Bendjeddou et al. (2003). For hydrogen-bond motifs, see: Etter et al. (1990); Grell et al. (1999).

Experimental top

Colourless crystals of compound (I) were grown by slow evaporation of an aquoes solution of 2-amino-pyridine-3-carboxylic acid and perchloric acid in an 1:1 stoichiometric ratio.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. asymmetric unit of the title compound with the atomic labelling scheme. Displacement are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. A view parallel to (010) showing cationic and anionic layers alternation along the c axis. Hydrogen bonds are shown as dashed lines.
	Fig. 3. A view of the two-dimensional network showing how dimers are stacked within cationic layers. Hydrogen bonds are shown as dashed lines.

2-Amino-3-carboxypyridinium perchlorate top

Crystal data top

C₆H₇N₂O₂⁺·ClO₄⁻	F(000) = 976
M_r = 238.59	D_x = 1.74 Mg m⁻³
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 3823 reflections
a = 17.3573 (12) Å	θ = 2.5–27.4°
b = 5.0800 (4) Å	µ = 0.43 mm⁻¹
c = 21.6293 (17) Å	T = 150 K
β = 107.239 (2)°	Stick, colourless
V = 1821.5 (2) Å³	0.48 × 0.17 × 0.08 mm
Z = 8

Data collection top

Bruker APEXII diffractometer	3305 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
CCD rotation images, thin slices scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −22→12
T_min = 0.847, T_max = 0.966	k = −6→6
13822 measured reflections	l = −27→28
4142 independent reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0377P)² + 1.7007P] where P = (F_o² + 2F_c²)/3
4142 reflections	(Δ/σ)_max < 0.001
273 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₆H₇N₂O₂⁺·ClO₄⁻	V = 1821.5 (2) Å³
M_r = 238.59	Z = 8
Monoclinic, P2/c	Mo Kα radiation
a = 17.3573 (12) Å	µ = 0.43 mm⁻¹
b = 5.0800 (4) Å	T = 150 K
c = 21.6293 (17) Å	0.48 × 0.17 × 0.08 mm
β = 107.239 (2)°

Data collection top

Bruker APEXII diffractometer	4142 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	3305 reflections with I > 2σ(I)
T_min = 0.847, T_max = 0.966	R_int = 0.044
13822 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.11	Δρ_max = 0.34 e Å⁻³
4142 reflections	Δρ_min = −0.40 e Å⁻³
273 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
Cl2	0.12456 (3)	−0.07231 (11)	−0.11690 (3)	0.01685 (14)
Cl1	0.37576 (3)	0.54151 (11)	0.35382 (3)	0.01875 (14)
O22	0.19785 (10)	−0.2141 (4)	−0.11310 (8)	0.0251 (4)
O1B	0.07544 (11)	0.1702 (4)	0.02704 (8)	0.0275 (4)
H1B	0.0786	0.0731	−0.0024	0.041*
O42	0.09107 (12)	−0.1755 (4)	−0.06809 (9)	0.0330 (5)
O21	0.42254 (13)	0.6540 (4)	0.31530 (9)	0.0369 (5)
O31	0.35147 (11)	0.2777 (3)	0.33137 (9)	0.0300 (4)
O41	0.30450 (11)	0.6993 (4)	0.34659 (8)	0.0264 (4)
O2B	0.18407 (11)	−0.0563 (4)	0.08267 (8)	0.0282 (4)
O32	0.14319 (11)	0.2034 (3)	−0.10376 (9)	0.0269 (4)
O2A	0.31277 (11)	0.5865 (4)	0.15454 (8)	0.0287 (4)
O11	0.42313 (11)	0.5324 (4)	0.42050 (8)	0.0269 (4)
O1A	0.42090 (11)	0.3499 (4)	0.20638 (8)	0.0323 (5)
H1A	0.4172	0.4352	0.2376	0.049*
O12	0.06824 (11)	−0.1019 (4)	−0.17999 (8)	0.0274 (4)
N2A	0.31083 (12)	0.1811 (4)	−0.01596 (9)	0.0189 (4)
H2A	0.2759	0.2114	−0.0528	0.023*
N2B	0.18027 (12)	0.3604 (4)	0.24939 (9)	0.0198 (4)
H2B	0.2137	0.3306	0.2869	0.024*
C3B	0.18684 (14)	0.2122 (4)	0.19911 (11)	0.0165 (5)
N1B	0.24371 (13)	0.0283 (4)	0.21094 (9)	0.0225 (5)
H11B	0.2751	0.0061	0.2496	0.027*
H12B	0.2492	−0.0685	0.1799	0.027*
C2B	0.13013 (14)	0.2659 (4)	0.13757 (11)	0.0156 (5)
C2A	0.36459 (14)	0.2707 (5)	0.09571 (11)	0.0166 (5)
N1A	0.24775 (12)	0.5022 (4)	0.02580 (9)	0.0204 (4)
H11A	0.2145	0.5237	−0.0122	0.025*
H12A	0.2432	0.5962	0.0576	0.025*
C3A	0.30586 (14)	0.3245 (4)	0.03538 (11)	0.0160 (5)
C5A	0.42317 (15)	−0.0621 (5)	0.04338 (12)	0.0239 (5)
H5A	0.4618	−0.1915	0.0457	0.029*
C6A	0.42192 (15)	0.0799 (5)	0.09851 (12)	0.0213 (5)
H6A	0.4605	0.0447	0.1378	0.026*
C4A	0.36681 (15)	−0.0065 (5)	−0.01335 (12)	0.0223 (5)
H4A	0.3666	−0.0978	−0.0507	0.027*
C6B	0.07394 (14)	0.4623 (5)	0.13287 (11)	0.0200 (5)
H6B	0.0373	0.4991	0.0927	0.024*
C1A	0.36249 (15)	0.4192 (5)	0.15434 (11)	0.0199 (5)
C1B	0.13334 (15)	0.1106 (5)	0.08066 (11)	0.0183 (5)
C4B	0.12476 (15)	0.5518 (5)	0.24461 (12)	0.0229 (5)
H4B	0.1238	0.6456	0.2813	0.027*
C5B	0.07058 (15)	0.6081 (5)	0.18698 (12)	0.0222 (5)
H5B	0.0322	0.7396	0.1833	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl2	0.0180 (3)	0.0159 (3)	0.0166 (3)	0.0000 (2)	0.0052 (2)	−0.0011 (2)
Cl1	0.0213 (3)	0.0159 (3)	0.0199 (3)	−0.0054 (2)	0.0074 (2)	−0.0038 (2)
O22	0.0216 (9)	0.0260 (10)	0.0251 (9)	0.0067 (7)	0.0028 (7)	−0.0018 (7)
O1B	0.0229 (10)	0.0384 (11)	0.0194 (9)	0.0070 (8)	0.0036 (7)	−0.0085 (8)
O42	0.0463 (12)	0.0321 (11)	0.0289 (10)	−0.0153 (9)	0.0242 (9)	−0.0079 (8)
O21	0.0472 (13)	0.0380 (12)	0.0356 (11)	−0.0184 (10)	0.0275 (10)	−0.0084 (9)
O31	0.0327 (11)	0.0164 (9)	0.0365 (11)	−0.0060 (8)	0.0034 (9)	−0.0079 (8)
O41	0.0268 (10)	0.0233 (9)	0.0271 (9)	0.0037 (8)	0.0050 (8)	−0.0032 (8)
O2B	0.0348 (11)	0.0259 (10)	0.0228 (9)	0.0121 (8)	0.0067 (8)	−0.0040 (8)
O32	0.0322 (11)	0.0143 (9)	0.0295 (10)	0.0002 (7)	0.0019 (8)	−0.0008 (7)
O2A	0.0334 (11)	0.0286 (10)	0.0225 (9)	0.0122 (8)	0.0058 (8)	−0.0031 (8)
O11	0.0237 (10)	0.0305 (10)	0.0227 (9)	−0.0036 (8)	0.0013 (7)	−0.0032 (8)
O1A	0.0249 (10)	0.0511 (13)	0.0176 (9)	0.0117 (9)	0.0010 (8)	−0.0044 (9)
O12	0.0232 (9)	0.0331 (11)	0.0214 (9)	0.0054 (8)	−0.0005 (7)	−0.0064 (8)
N2A	0.0215 (11)	0.0188 (10)	0.0156 (9)	0.0020 (8)	0.0044 (8)	0.0008 (8)
N2B	0.0230 (11)	0.0192 (10)	0.0165 (9)	−0.0029 (8)	0.0047 (8)	−0.0026 (8)
C3B	0.0185 (12)	0.0137 (11)	0.0182 (11)	−0.0045 (9)	0.0071 (9)	−0.0022 (9)
N1B	0.0279 (12)	0.0187 (10)	0.0182 (10)	0.0048 (9)	0.0024 (8)	−0.0005 (8)
C2B	0.0167 (12)	0.0127 (10)	0.0186 (11)	−0.0040 (9)	0.0071 (9)	−0.0013 (9)
C2A	0.0149 (12)	0.0162 (11)	0.0190 (11)	−0.0007 (9)	0.0055 (9)	0.0020 (9)
N1A	0.0227 (11)	0.0177 (10)	0.0178 (9)	0.0073 (8)	0.0012 (8)	−0.0002 (8)
C3A	0.0177 (12)	0.0125 (10)	0.0186 (11)	−0.0025 (9)	0.0067 (9)	0.0012 (9)
C5A	0.0213 (13)	0.0204 (12)	0.0326 (13)	0.0071 (10)	0.0120 (11)	0.0006 (11)
C6A	0.0187 (12)	0.0225 (12)	0.0222 (12)	0.0015 (10)	0.0050 (10)	0.0044 (10)
C4A	0.0267 (13)	0.0174 (12)	0.0260 (12)	0.0003 (10)	0.0127 (10)	−0.0035 (10)
C6B	0.0179 (12)	0.0187 (12)	0.0230 (11)	−0.0025 (10)	0.0053 (9)	−0.0005 (10)
C1A	0.0219 (13)	0.0201 (12)	0.0176 (11)	−0.0015 (10)	0.0056 (10)	0.0014 (9)
C1B	0.0201 (12)	0.0169 (12)	0.0183 (11)	−0.0018 (10)	0.0062 (9)	−0.0009 (9)
C4B	0.0279 (14)	0.0193 (12)	0.0251 (12)	−0.0043 (11)	0.0135 (10)	−0.0075 (10)
C5B	0.0213 (13)	0.0174 (12)	0.0302 (13)	0.0012 (10)	0.0112 (11)	−0.0047 (10)

Geometric parameters (Å, º) top

Cl2—O12	1.4316 (17)	C3B—C2B	1.428 (3)
Cl2—O22	1.4427 (18)	N1B—H11B	0.86
Cl2—O42	1.4463 (18)	N1B—H12B	0.86
Cl2—O32	1.4466 (18)	C2B—C6B	1.378 (3)
Cl1—O11	1.4336 (17)	C2B—C1B	1.477 (3)
Cl1—O21	1.4427 (19)	C2A—C6A	1.378 (3)
Cl1—O41	1.4430 (18)	C2A—C3A	1.424 (3)
Cl1—O31	1.4451 (18)	C2A—C1A	1.485 (3)
O1B—C1B	1.325 (3)	N1A—C3A	1.324 (3)
O1B—H1B	0.82	N1A—H11A	0.86
O2B—C1B	1.214 (3)	N1A—H12A	0.86
O2A—C1A	1.212 (3)	C5A—C4A	1.353 (3)
O1A—C1A	1.320 (3)	C5A—C6A	1.399 (3)
O1A—H1A	0.82	C5A—H5A	0.93
N2A—C4A	1.350 (3)	C6A—H6A	0.93
N2A—C3A	1.352 (3)	C4A—H4A	0.93
N2A—H2A	0.86	C6B—C5B	1.401 (3)
N2B—C4B	1.351 (3)	C6B—H6B	0.93
N2B—C3B	1.355 (3)	C4B—C5B	1.351 (3)
N2B—H2B	0.86	C4B—H4B	0.93
C3B—N1B	1.328 (3)	C5B—H5B	0.93

O12—Cl2—O22	110.08 (10)	C3A—C2A—C1A	119.5 (2)
O12—Cl2—O42	110.43 (12)	C3A—N1A—H11A	120
O22—Cl2—O42	108.41 (12)	C3A—N1A—H12A	120
O12—Cl2—O32	109.81 (11)	H11A—N1A—H12A	120
O22—Cl2—O32	109.27 (11)	N1A—C3A—N2A	118.0 (2)
O42—Cl2—O32	108.81 (11)	N1A—C3A—C2A	125.4 (2)
O11—Cl1—O21	109.92 (11)	N2A—C3A—C2A	116.5 (2)
O11—Cl1—O41	110.16 (11)	C4A—C5A—C6A	118.4 (2)
O21—Cl1—O41	109.17 (12)	C4A—C5A—H5A	120.8
O11—Cl1—O31	109.34 (11)	C6A—C5A—H5A	120.8
O21—Cl1—O31	109.36 (12)	C2A—C6A—C5A	121.2 (2)
O41—Cl1—O31	108.87 (11)	C2A—C6A—H6A	119.4
C1B—O1B—H1B	109.5	C5A—C6A—H6A	119.4
C1A—O1A—H1A	109.5	N2A—C4A—C5A	120.2 (2)
C4A—N2A—C3A	124.5 (2)	N2A—C4A—H4A	119.9
C4A—N2A—H2A	117.8	C5A—C4A—H4A	119.9
C3A—N2A—H2A	117.8	C2B—C6B—C5B	121.7 (2)
C4B—N2B—C3B	124.5 (2)	C2B—C6B—H6B	119.2
C4B—N2B—H2B	117.8	C5B—C6B—H6B	119.2
C3B—N2B—H2B	117.8	O2A—C1A—O1A	123.5 (2)
N1B—C3B—N2B	118.1 (2)	O2A—C1A—C2A	123.8 (2)
N1B—C3B—C2B	125.6 (2)	O1A—C1A—C2A	112.7 (2)
N2B—C3B—C2B	116.3 (2)	O2B—C1B—O1B	123.0 (2)
C3B—N1B—H11B	120	O2B—C1B—C2B	123.3 (2)
C3B—N1B—H12B	120	O1B—C1B—C2B	113.6 (2)
H11B—N1B—H12B	120	C5B—C4B—N2B	120.6 (2)
C6B—C2B—C3B	119.0 (2)	C5B—C4B—H4B	119.7
C6B—C2B—C1B	121.7 (2)	N2B—C4B—H4B	119.7
C3B—C2B—C1B	119.3 (2)	C4B—C5B—C6B	118.0 (2)
C6A—C2A—C3A	119.1 (2)	C4B—C5B—H5B	121
C6A—C2A—C1A	121.3 (2)	C6B—C5B—H5B	121

C4B—N2B—C3B—N1B	−179.2 (2)	C3A—N2A—C4A—C5A	−0.1 (4)
C4B—N2B—C3B—C2B	−0.3 (3)	C6A—C5A—C4A—N2A	−0.3 (4)
N1B—C3B—C2B—C6B	179.4 (2)	C3B—C2B—C6B—C5B	−0.7 (4)
N2B—C3B—C2B—C6B	0.7 (3)	C1B—C2B—C6B—C5B	179.5 (2)
N1B—C3B—C2B—C1B	−0.8 (4)	C6A—C2A—C1A—O2A	−179.1 (2)
N2B—C3B—C2B—C1B	−179.6 (2)	C3A—C2A—C1A—O2A	0.4 (4)
C4A—N2A—C3A—N1A	−180.0 (2)	C6A—C2A—C1A—O1A	1.1 (3)
C4A—N2A—C3A—C2A	0.2 (3)	C3A—C2A—C1A—O1A	−179.4 (2)
C6A—C2A—C3A—N1A	−179.8 (2)	C6B—C2B—C1B—O2B	176.9 (2)
C1A—C2A—C3A—N1A	0.7 (4)	C3B—C2B—C1B—O2B	−2.8 (4)
C6A—C2A—C3A—N2A	0.0 (3)	C6B—C2B—C1B—O1B	−3.2 (3)
C1A—C2A—C3A—N2A	−179.6 (2)	C3B—C2B—C1B—O1B	177.1 (2)
C3A—C2A—C6A—C5A	−0.3 (4)	C3B—N2B—C4B—C5B	0.0 (4)
C1A—C2A—C6A—C5A	179.2 (2)	N2B—C4B—C5B—C6B	0.0 (4)
C4A—C5A—C6A—C2A	0.5 (4)	C2B—C6B—C5B—C4B	0.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O21	0.82	1.99	2.810 (3)	173
O1B—H1B···O42	0.82	1.96	2.779 (3)	176
N2A—H2A···O32	0.86	2.24	2.968 (3)	142
N2A—H2A···O41ⁱ	0.86	2.41	3.004 (3)	126
N2B—H2B···O31	0.86	2.31	3.005 (3)	138
N2B—H2B···O41	0.86	2.54	3.057 (3)	120
N2B—H2B···O22ⁱⁱ	0.86	2.34	2.992 (3)	133
N1A—H11A···O22ⁱⁱⁱ	0.86	2.50	3.211 (3)	141
N1A—H11A···O32	0.86	2.58	3.231 (3)	133
N1B—H11B···O31	0.86	2.32	3.000 (3)	136
N1B—H11B···O41^iv	0.86	2.54	3.268 (3)	143
N1A—H12A···O2A	0.86	2.09	2.711 (3)	129
N1A—H12A···O2Bⁱⁱⁱ	0.86	2.19	2.928 (3)	144
N1B—H12B···O2A^iv	0.86	2.22	2.971 (3)	145
N1B—H12B···O2B	0.86	2.07	2.693 (3)	128
C4A—H4A···O11^v	0.93	2.57	3.312 (3)	137
C4B—H4B···O32^vi	0.93	2.53	3.433 (3)	165
C5A—H5A···O11^vii	0.93	2.37	3.277 (3)	164
C5B—H5B···O12^viii	0.93	2.52	3.450 (3)	177
C6A—H6A···O1A	0.93	2.38	2.711 (3)	100
C6B—H6B···O1B	0.93	2.41	2.735 (3)	100

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

Experimental details

Crystal data
Chemical formula	C₆H₇N₂O₂⁺·ClO₄⁻
M_r	238.59
Crystal system, space group	Monoclinic, P2/c
Temperature (K)	150
a, b, c (Å)	17.3573 (12), 5.0800 (4), 21.6293 (17)
β (°)	107.239 (2)
V (Å³)	1821.5 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.48 × 0.17 × 0.08

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2002)
T_min, T_max	0.847, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	13822, 4142, 3305
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.110, 1.11
No. of reflections	4142
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.40

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SIR2002 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O21	0.82	1.99	2.810 (3)	173
O1B—H1B···O42	0.82	1.96	2.779 (3)	176
N2A—H2A···O32	0.86	2.24	2.968 (3)	142
N2B—H2B···O31	0.86	2.31	3.005 (3)	138
N2B—H2B···O22ⁱ	0.86	2.34	2.992 (3)	133
N1A—H11A···O22ⁱⁱ	0.86	2.50	3.211 (3)	141
N1A—H11A···O32	0.86	2.58	3.231 (3)	133
N1B—H11B···O31	0.86	2.32	3.000 (3)	136
N1B—H11B···O41ⁱⁱⁱ	0.86	2.54	3.268 (3)	143
N1A—H12A···O2Bⁱⁱ	0.86	2.19	2.928 (3)	144
N1B—H12B···O2Aⁱⁱⁱ	0.86	2.22	2.971 (3)	145
C4A—H4A···O11^iv	0.93	2.57	3.312 (3)	137
C4B—H4B···O32^v	0.93	2.53	3.433 (3)	165
C5A—H5A···O11^vi	0.93	2.37	3.277 (3)	164
C5B—H5B···O12^vii	0.93	2.52	3.450 (3)	177

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

Acknowledgements

We are grateful to the LCATM laboratory, Université d'Oum El Bouaghi, Algeria, for financial support.

References

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