Hydrogen bonding in 1-carb­oxy­propanaminium nitrate

Messai, A.; Benali-Cherif, R.; Jeanneau, E.; Benali-Cherif, N.

doi:10.1107/S1600536812013682

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1307-o1308

doi:10.1107/S1600536812013682

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Hydrogen bonding in 1-carboxypropanaminium nitrate

Amel Messai,^a Rim Benali-Cherif,^a ^* Erwann Jeanneau ^b and Nourredine Benali-Cherif ^a

^aLaboratoire des Structures, Propriétés et Interactions Interatomiques, Université Abbes Laghrour Khenchela, 40000 Khenchela, Algeria, and ^bUniversité Claude Bernard Lyon 1, Laboratoire des Multimatériaux et Interfaces (UMR 5615), 69622 Villeurbanne Cedex, France
^*Correspondence e-mail: benalicherif@hotmail.com

(Received 7 March 2012; accepted 29 March 2012; online 4 April 2012)

There are two crystallographically independent cations and two anions in the asymmetric unit of the title compound, C₄H₅NO₂⁺·NO₃⁻. In the crystal, the 1-carboxypropanaminium cations and nitrate anions are linked to each other through strong N—H⋯O and O—H⋯O hydrogen bonds, forming a three-dimensional complex network. C—H⋯O interactions also occur.

Related literature

For background to inorganic–organic hybrid materials, see: Benali-Cherif, Allouche et al. (2007 ); Benali-Cherif, Kateb et al. (2007 ); Messai et al. (2009 ); Cherouana et al. (2003 ). Changes in illuminated volume were kept to a minimum, and were taken into account (Görbitz, 1999 ) by multi-scan inter-frame scaling.

Experimental

Crystal data

C₄H₁₀NO₂⁺·NO₃⁻
M_r = 166.14
Monoclinic, P 2₁ /c
a = 18.274 (2) Å
b = 5.6052 (4) Å
c = 16.536 (2) Å
β = 116.224 (16)°
V = 1519.4 (3) Å³
Z = 8
Cu Kα radiation
μ = 1.18 mm⁻¹
T = 150 K
0.1 × 0.02 × 0.01 mm

Data collection

Oxford Xcalibur Atlas Gemini ultra diffractometer
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.987, T_max = 0.999
14871 measured reflections
2683 independent reflections
2441 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.109
S = 1.08
2683 reflections
203 parameters
H-atom parameters not refined
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1A⋯O1Aⁱ	0.89	2.11	2.8590 (18)	141
N1A—H1A⋯O5Bⁱⁱ	0.89	2.48	2.9464 (18)	113
N1A—H1B⋯O3Bⁱⁱⁱ	0.89	2.01	2.8877 (17)	169
N1A—H1B⋯O4Bⁱⁱⁱ	0.89	2.44	3.0033 (16)	121
N1A—H1C⋯O4B	0.89	1.93	2.8162 (16)	173
O2A—H2O⋯O3B^iv	0.82	1.84	2.6295 (17)	160
N1B—H3C⋯O1B^v	0.89	2.08	2.8470 (16)	143
N1B—H3C⋯O5A^v	0.89	2.50	2.946 (2)	111
N1B—H3D⋯O3A^vi	0.89	2.47	2.9917 (16)	118
N1B—H3D⋯O4A^vi	0.89	2.02	2.9025 (16)	169
N1B—H3E⋯O3A^vii	0.89	1.94	2.8126 (16)	168
O2B—H4⋯O4A	0.82	1.84	2.6206 (16)	159
C4A—H4B⋯O3Bⁱⁱⁱ	0.96	2.58	3.382 (2)	141
C2B—H6⋯O3A^vi	0.98	2.57	3.189 (2)	121
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z; (iii) x, y-1, z; (iv) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (v) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (vii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: Gemini User Manual (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). Gemini User Manual. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812013682/ru2030sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013682/ru2030Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812013682/ru2030Isup3.cml

checkCIF report

Comment top

Inorganic organic hybrid materials have been studied extensively because the blending of organic and inorganic components allows to the development of materials with novel properties. (Cherouana et al., 2003; Benali-Cherif, Allouche et al., 2007; Benali-Cherif, Kateb et al., 2007; Messai et al., 2009; In particular the family of material which combine nitrate anions with organic molecules such as aromatic and aliphatic aminoacids has been studied intensively due to their numerous uses in various fields such as biomolecular science, liquid crystals, catalysts and fuel cells.

As a contribution to the study of thiscompound family, we report in this work the synthesis and the crystal structure of a new organic cation nitrate (C₄H₅O₂N)⁺(N O₃)^- (I). The asymmetric unit in the structure of (I) contains two nitrate anions and two crystallographically independent monoprotonated 2-Ammonium butyric acid cations (Fig. 1). wich one one of these cations is R configuration and the second was the S configration. In the nitrate anions, two of the N_O distances, involving atoms O3 and O4, are slightly longer than the third, involving atom O5, while the O_N···O angles range from 117.6 (3) to 121.7 (3). The bond distances and angles of 2-Ammonium butyric acid cation are normal. The nitrate anion in (I) plays an important role in hydrogen bonding, with all three O atoms (O3, O4 and O5) being involved. The 2-Ammonium butyric acid residue forms three strong O_H··· O hydrogen bonds with the nitrate anion. The amino N atom of the phenylglycinium residue forms eight N_H···O hydrogen bonds via atoms O1, O2 and O3 of the nitrate anion, and two via the carboxyl atom O4 (Fig. 2).

Related literature top

For background to inorganic–organic hybrid materials, see: Benali-Cherif, Allouche et al. (2007); Benali-Cherif, Kateb et al. (2007); Messai et al. (2009); Cherouana et al. (2003). Changes in illuminated volume were kept to a minimum, and were taken into account (Görbitz, 1999) by multi-scan inter-frame scaling.

Experimental top

colorlesse single crystals of this compound were obtained after a few days by slow evaporation, at room temperature, of an equimolar aqueous solution of 2-amino butyric acid and nitric acid.

Computing details top

Data collection: Gemini User Manual (Oxford Diffraction, 2006); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997)and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Aview of (I), showing the atomic labelling scheme and with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. packing view of the hydrogen-bonding network

1-carboxypropanaminium nitrate top

Crystal data top

C₄H₁₀NO₂⁺·NO₃⁻	F(000) = 704
M_r = 166.14	D_x = 1.453 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 7884 reflections
a = 18.274 (2) Å	θ = 4.8–66.5°
b = 5.6052 (4) Å	µ = 1.18 mm⁻¹
c = 16.536 (2) Å	T = 150 K
β = 116.224 (16)°	Needle, colorless
V = 1519.4 (3) Å³	0.1 × 0.02 × 0.01 mm
Z = 8

Data collection top

Oxford Xcalibur Atlas Gemini ultra diffractometer	2683 independent reflections
Radiation source: fine-focus sealed tube	2441 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
Detector resolution: 10.4685 pixels mm^-1	θ_max = 66.6°, θ_min = 5.4°
ω scans	h = −21→21
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010)	k = −6→6
T_min = 0.987, T_max = 0.999	l = −19→19
14871 measured 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters not refined
S = 1.08	w = 1/[σ²(F_o²) + (0.0631P)² + 0.5656P] where P = (F_o² + 2F_c²)/3
2683 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₄H₁₀NO₂⁺·NO₃⁻	V = 1519.4 (3) Å³
M_r = 166.14	Z = 8
Monoclinic, P2₁/c	Cu Kα radiation
a = 18.274 (2) Å	µ = 1.18 mm⁻¹
b = 5.6052 (4) Å	T = 150 K
c = 16.536 (2) Å	0.1 × 0.02 × 0.01 mm
β = 116.224 (16)°

Data collection top

Oxford Xcalibur Atlas Gemini ultra diffractometer	2683 independent reflections
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010)	2441 reflections with I > 2σ(I)
T_min = 0.987, T_max = 0.999	R_int = 0.054
14871 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.109	H-atom parameters not refined
S = 1.08	Δρ_max = 0.25 e Å⁻³
2683 reflections	Δρ_min = −0.31 e Å⁻³
203 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
O1A	0.05317 (6)	0.57372 (18)	0.29774 (7)	0.0216 (3)
O2A	0.11711 (7)	0.2856 (2)	0.39898 (7)	0.0261 (3)
H2O	0.1042	0.3668	0.4319	0.039*
N1A	0.06545 (7)	0.3190 (2)	0.16452 (8)	0.0153 (3)
H1A	0.0142	0.2831	0.1526	0.023*
H1B	0.0799	0.2372	0.1277	0.023*
H1C	0.0693	0.4746	0.1563	0.023*
C1A	0.09177 (9)	0.3901 (3)	0.32014 (10)	0.0163 (3)
C2A	0.12050 (8)	0.2556 (2)	0.25965 (9)	0.0152 (3)
H2	0.1166	0.0838	0.2680	0.018*
C3A	0.20896 (9)	0.3193 (3)	0.28412 (11)	0.0216 (3)
H3A	0.2119	0.4876	0.2722	0.026*
H3B	0.2415	0.2939	0.3482	0.026*
C4A	0.24575 (10)	0.1760 (3)	0.23296 (12)	0.0299 (4)
H4A	0.3012	0.2252	0.2515	0.045*
H4B	0.2148	0.2030	0.1694	0.045*
H4C	0.2445	0.0093	0.2456	0.045*
O1B	0.45105 (7)	0.41637 (18)	0.24898 (7)	0.0221 (3)
O2B	0.37874 (8)	0.6976 (2)	0.27877 (8)	0.0294 (3)
H4	0.3942	0.6267	0.3269	0.044*
N1B	0.43613 (7)	0.6551 (2)	0.09954 (8)	0.0154 (3)
H3C	0.4859	0.7012	0.1386	0.023*
H3D	0.4215	0.7326	0.0477	0.023*
H3E	0.4362	0.4988	0.0900	0.023*
C1B	0.40800 (9)	0.5918 (3)	0.22859 (10)	0.0173 (3)
C2B	0.37732 (9)	0.7096 (2)	0.13665 (9)	0.0163 (3)
H6	0.3747	0.8827	0.1434	0.020*
C3B	0.29190 (9)	0.6152 (3)	0.07476 (10)	0.0243 (4)
H7A	0.2946	0.4431	0.0704	0.029*
H7B	0.2557	0.6503	0.1019	0.029*
C4B	0.25584 (10)	0.7202 (4)	−0.01973 (11)	0.0341 (4)
H8A	0.2026	0.6538	−0.0548	0.051*
H8B	0.2906	0.6829	−0.0478	0.051*
H8C	0.2516	0.8902	−0.0163	0.051*
O4B	0.08435 (8)	0.80167 (19)	0.13033 (7)	0.0262 (3)
O3B	0.08960 (7)	1.04237 (18)	0.03095 (7)	0.0226 (3)
N2A	0.08566 (7)	0.8294 (2)	0.05545 (8)	0.0170 (3)
O3A	0.41482 (8)	0.32834 (19)	0.54878 (8)	0.0275 (3)
O4A	0.41008 (7)	0.56070 (17)	0.44238 (7)	0.0212 (3)
O5A	0.41568 (7)	0.17533 (18)	0.42863 (8)	0.0246 (3)
N2B	0.41346 (7)	0.3502 (2)	0.47249 (8)	0.0173 (3)
O5B	0.08332 (7)	0.65860 (18)	0.00782 (8)	0.0248 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0271 (6)	0.0212 (6)	0.0200 (6)	0.0077 (4)	0.0136 (5)	0.0009 (4)
O2A	0.0408 (7)	0.0267 (6)	0.0164 (6)	0.0118 (5)	0.0178 (5)	0.0036 (4)
N1A	0.0201 (6)	0.0136 (6)	0.0140 (6)	−0.0013 (4)	0.0092 (5)	−0.0015 (4)
C1A	0.0190 (7)	0.0164 (7)	0.0154 (7)	−0.0021 (5)	0.0093 (6)	−0.0007 (5)
C2A	0.0193 (7)	0.0140 (6)	0.0134 (7)	0.0017 (5)	0.0082 (6)	0.0002 (5)
C3A	0.0195 (8)	0.0246 (8)	0.0201 (8)	0.0000 (6)	0.0083 (6)	−0.0039 (6)
C4A	0.0227 (8)	0.0391 (10)	0.0325 (9)	−0.0003 (7)	0.0163 (7)	−0.0078 (7)
O1B	0.0280 (6)	0.0220 (6)	0.0182 (5)	0.0087 (4)	0.0119 (5)	0.0064 (4)
O2B	0.0450 (7)	0.0321 (6)	0.0190 (6)	0.0178 (5)	0.0213 (6)	0.0091 (5)
N1B	0.0197 (6)	0.0141 (6)	0.0141 (6)	−0.0016 (4)	0.0091 (5)	0.0000 (4)
C1B	0.0215 (7)	0.0164 (7)	0.0156 (7)	−0.0004 (5)	0.0096 (6)	−0.0005 (5)
C2B	0.0210 (7)	0.0157 (7)	0.0153 (7)	0.0030 (5)	0.0110 (6)	0.0021 (5)
C3B	0.0191 (8)	0.0329 (8)	0.0212 (8)	0.0008 (6)	0.0092 (7)	0.0065 (6)
C4B	0.0230 (9)	0.0497 (11)	0.0232 (9)	−0.0038 (8)	0.0043 (7)	0.0112 (8)
O4B	0.0474 (7)	0.0192 (5)	0.0168 (6)	−0.0034 (5)	0.0184 (5)	0.0011 (4)
O3B	0.0373 (6)	0.0165 (5)	0.0196 (6)	−0.0017 (4)	0.0176 (5)	0.0019 (4)
N2A	0.0198 (6)	0.0173 (6)	0.0143 (6)	−0.0006 (5)	0.0079 (5)	−0.0013 (5)
O3A	0.0522 (8)	0.0186 (5)	0.0228 (6)	0.0024 (5)	0.0268 (6)	0.0028 (4)
O4A	0.0334 (6)	0.0158 (5)	0.0176 (5)	0.0026 (4)	0.0140 (5)	0.0034 (4)
O5A	0.0320 (6)	0.0208 (5)	0.0242 (6)	−0.0005 (4)	0.0153 (5)	−0.0083 (4)
N2B	0.0199 (6)	0.0172 (6)	0.0168 (6)	0.0005 (5)	0.0099 (5)	−0.0002 (5)
O5B	0.0321 (6)	0.0208 (6)	0.0235 (6)	0.0007 (4)	0.0141 (5)	−0.0079 (4)

Geometric parameters (Å, º) top

O1A—C1A	1.2098 (18)	N1B—C2B	1.4859 (17)
O2A—C1A	1.3127 (18)	N1B—H3C	0.8900
O2A—H2O	0.8200	N1B—H3D	0.8900
N1A—C2A	1.4880 (18)	N1B—H3E	0.8900
N1A—H1A	0.8900	C1B—C2B	1.520 (2)
N1A—H1B	0.8900	C2B—C3B	1.534 (2)
N1A—H1C	0.8900	C2B—H6	0.9800
C1A—C2A	1.5193 (19)	C3B—C4B	1.521 (2)
C2A—C3A	1.525 (2)	C3B—H7A	0.9700
C2A—H2	0.9800	C3B—H7B	0.9700
C3A—C4A	1.522 (2)	C4B—H8A	0.9600
C3A—H3A	0.9700	C4B—H8B	0.9600
C3A—H3B	0.9700	C4B—H8C	0.9600
C4A—H4A	0.9600	O4B—N2A	1.2586 (16)
C4A—H4B	0.9600	O3B—N2A	1.2727 (16)
C4A—H4C	0.9600	N2A—O5B	1.2285 (16)
O1B—C1B	1.2103 (18)	O3A—N2B	1.2568 (16)
O2B—C1B	1.3108 (18)	O4A—N2B	1.2714 (16)
O2B—H4	0.8200	O5A—N2B	1.2307 (16)

C1A—O2A—H2O	109.5	H3C—N1B—H3D	109.5
C2A—N1A—H1A	109.5	C2B—N1B—H3E	109.5
C2A—N1A—H1B	109.5	H3C—N1B—H3E	109.5
H1A—N1A—H1B	109.5	H3D—N1B—H3E	109.5
C2A—N1A—H1C	109.5	O1B—C1B—O2B	126.01 (13)
H1A—N1A—H1C	109.5	O1B—C1B—C2B	122.62 (13)
H1B—N1A—H1C	109.5	O2B—C1B—C2B	111.30 (12)
O1A—C1A—O2A	125.85 (13)	N1B—C2B—C1B	108.01 (11)
O1A—C1A—C2A	123.02 (13)	N1B—C2B—C3B	111.22 (12)
O2A—C1A—C2A	111.08 (12)	C1B—C2B—C3B	109.52 (12)
N1A—C2A—C1A	107.98 (11)	N1B—C2B—H6	109.4
N1A—C2A—C3A	111.51 (11)	C1B—C2B—H6	109.4
C1A—C2A—C3A	110.08 (12)	C3B—C2B—H6	109.4
N1A—C2A—H2	109.1	C4B—C3B—C2B	113.77 (13)
C1A—C2A—H2	109.1	C4B—C3B—H7A	108.8
C3A—C2A—H2	109.1	C2B—C3B—H7A	108.8
C4A—C3A—C2A	113.94 (13)	C4B—C3B—H7B	108.8
C4A—C3A—H3A	108.8	C2B—C3B—H7B	108.8
C2A—C3A—H3A	108.8	H7A—C3B—H7B	107.7
C4A—C3A—H3B	108.8	C3B—C4B—H8A	109.5
C2A—C3A—H3B	108.8	C3B—C4B—H8B	109.5
H3A—C3A—H3B	107.7	H8A—C4B—H8B	109.5
C3A—C4A—H4A	109.5	C3B—C4B—H8C	109.5
C3A—C4A—H4B	109.5	H8A—C4B—H8C	109.5
H4A—C4A—H4B	109.5	H8B—C4B—H8C	109.5
C3A—C4A—H4C	109.5	O5B—N2A—O4B	121.59 (12)
H4A—C4A—H4C	109.5	O5B—N2A—O3B	121.18 (11)
H4B—C4A—H4C	109.5	O4B—N2A—O3B	117.22 (11)
C1B—O2B—H4	109.5	O5A—N2B—O3A	121.51 (12)
C2B—N1B—H3C	109.5	O5A—N2B—O4A	121.13 (12)
C2B—N1B—H3D	109.5	O3A—N2B—O4A	117.36 (11)

O1A—C1A—C2A—N1A	−24.57 (18)	O1B—C1B—C2B—N1B	−26.22 (19)
O2A—C1A—C2A—N1A	157.91 (12)	O2B—C1B—C2B—N1B	156.73 (12)
O1A—C1A—C2A—C3A	97.38 (16)	O1B—C1B—C2B—C3B	95.05 (16)
O2A—C1A—C2A—C3A	−80.14 (15)	O2B—C1B—C2B—C3B	−82.00 (15)
N1A—C2A—C3A—C4A	−65.55 (16)	N1B—C2B—C3B—C4B	−60.01 (17)
C1A—C2A—C3A—C4A	174.63 (13)	C1B—C2B—C3B—C4B	−179.33 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O1Aⁱ	0.89	2.11	2.8590 (18)	141
N1A—H1A···O5Bⁱⁱ	0.89	2.48	2.9464 (18)	113
N1A—H1B···O3Bⁱⁱⁱ	0.89	2.01	2.8877 (17)	169
N1A—H1B···O4Bⁱⁱⁱ	0.89	2.44	3.0033 (16)	121
N1A—H1C···O4B	0.89	1.93	2.8162 (16)	173
O2A—H2O···O3B^iv	0.82	1.84	2.6295 (17)	160
N1B—H3C···O1B^v	0.89	2.08	2.8470 (16)	143
N1B—H3C···O5A^v	0.89	2.50	2.946 (2)	111
N1B—H3D···O3A^vi	0.89	2.47	2.9917 (16)	118
N1B—H3D···O4A^vi	0.89	2.02	2.9025 (16)	169
N1B—H3E···O3A^vii	0.89	1.94	2.8126 (16)	168
O2B—H4···O4A	0.82	1.84	2.6206 (16)	159
C4A—H4B···O3Bⁱⁱⁱ	0.96	2.58	3.382 (2)	141
C2B—H6···O3A^vi	0.98	2.57	3.189 (2)	121

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, −y+1, −z; (iii) x, y−1, z; (iv) x, −y+3/2, z+1/2; (v) −x+1, y+1/2, −z+1/2; (vi) x, −y+3/2, z−1/2; (vii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₄H₁₀NO₂⁺·NO₃⁻
M_r	166.14
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	18.274 (2), 5.6052 (4), 16.536 (2)
β (°)	116.224 (16)
V (Å³)	1519.4 (3)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	1.18
Crystal size (mm)	0.1 × 0.02 × 0.01

Data collection
Diffractometer	Oxford Xcalibur Atlas Gemini ultra diffractometer
Absorption correction	Analytical (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.987, 0.999
No. of measured, independent and observed [I > 2σ(I)] reflections	14871, 2683, 2441
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.109, 1.08
No. of reflections	2683
No. of parameters	203
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.31

Computer programs: Gemini User Manual (Oxford Diffraction, 2006), CrysAlis PRO (Oxford Diffraction, 2010), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997)and PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O1Aⁱ	0.8900	2.1100	2.8590 (18)	141.00
N1A—H1A···O5Bⁱⁱ	0.8900	2.4800	2.9464 (18)	113.00
N1A—H1B···O3Bⁱⁱⁱ	0.8900	2.0100	2.8877 (17)	169.00
N1A—H1B···O4Bⁱⁱⁱ	0.8900	2.4400	3.0033 (16)	121.00
N1A—H1C···O4B	0.8900	1.9300	2.8162 (16)	173.00
O2A—H2O···O3B^iv	0.8200	1.8400	2.6295 (17)	160.00
N1B—H3C···O1B^v	0.8900	2.0800	2.8470 (16)	143.00
N1B—H3C···O5A^v	0.8900	2.5000	2.946 (2)	111.00
N1B—H3D···O3A^vi	0.8900	2.4700	2.9917 (16)	118.00
N1B—H3D···O4A^vi	0.8900	2.0200	2.9025 (16)	169.00
N1B—H3E···O3A^vii	0.8900	1.9400	2.8126 (16)	168.00
O2B—H4···O4A	0.8200	1.8400	2.6206 (16)	159.00
C4A—H4B···O3Bⁱⁱⁱ	0.9600	2.5800	3.382 (2)	141.00
C2B—H6···O3A^vi	0.9800	2.5700	3.189 (2)	121.00

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, −y+1, −z; (iii) x, y−1, z; (iv) x, −y+3/2, z+1/2; (v) −x+1, y+1/2, −z+1/2; (vi) x, −y+3/2, z−1/2; (vii) x, −y+1/2, z−1/2.

Acknowledgements

We thank Professor Dominique Luneau (Laboratoire des Multimatériaux et Interfaces UMR 5615, Université Claude Bernard Lyon 1, France) for the diffraction facilities. We also thank Abbes Laghrour Khenchela University and the Ministère de l'Enseignement Supérieur et de la Recherche Scientifique–Algeria for financial support via the PNE programme.

References

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