Hydrogen bonding in 1-carb-oxy-propanaminium nitrate.

There are two crystallographically independent cations and two anions in the asymmetric unit of the title compound, C(4)H(5)NO(2) (+)·NO(3) (-). In the crystal, the 1-carb-oxy-propanaminium 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 inter-actions 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 = 166.14

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.08

2683 reflections

203 parameters

H-atom parameters not refined

Δρmax = 0.25 e Å−3

Δρmin = −0.31 e Å−3

Data collection: Gemini User Manual (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010 ▶); 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812013682/ru2030sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812013682/ru2030Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C4H10NO2+·NO3−	F(000) = 704
Mr = 166.14	Dx = 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

Oxford Xcalibur Atlas Gemini ultra diffractometer	2683 independent reflections
Radiation source: fine-focus sealed tube	2441 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
Detector resolution: 10.4685 pixels mm-1	θmax = 66.6°, θmin = 5.4°
ω scans	h = −21→21
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2010)	k = −6→6
Tmin = 0.987, Tmax = 0.999	l = −19→19
14871 measured reflections

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(Fo2) + (0.0631P)2 + 0.5656P] where P = (Fo2 + 2Fc2)/3
2683 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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···O3Biv	0.82	1.84	2.6295 (17)	160
N1B—H3C···O1Bv	0.89	2.08	2.8470 (16)	143
N1B—H3C···O5Av	0.89	2.50	2.946 (2)	111
N1B—H3D···O3Avi	0.89	2.47	2.9917 (16)	118
N1B—H3D···O4Avi	0.89	2.02	2.9025 (16)	169
N1B—H3E···O3Avii	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···O3Avi	0.98	2.57	3.189 (2)	121

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⋯O3Biv	0.82	1.84	2.6295 (17)	160
N1B—H3C⋯O1Bv	0.89	2.08	2.8470 (16)	143
N1B—H3C⋯O5Av	0.89	2.50	2.946 (2)	111
N1B—H3D⋯O3Avi	0.89	2.47	2.9917 (16)	118
N1B—H3D⋯O4Avi	0.89	2.02	2.9025 (16)	169
N1B—H3E⋯O3Avii	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⋯O3Avi	0.98	2.57	3.189 (2)	121

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .