Download citation
Download citation
link to html
In the title compound, C5H13N2O2+·NO3, both the α- and δ-amino N atoms form strong N—H...O hydrogen bonds with the carboxyl group and nitrate anions. The straight side-chain conformation shows an all trans form.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802008358/ci6124sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802008358/ci6124Isup2.hkl
Contains datablock I

CCDC reference: 189384

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.037
  • wR factor = 0.090
  • Data-to-parameter ratio = 7.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFNR_01 Alert C Ratio of reflections to parameters is < 8 for a non-centrosymmetric structure, where ZMAX < 18 sine(theta)/lambda 0.5951 Proportion of unique data used 0.8702 Ratio reflections to parameters 7.0420 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.02 From the CIF: _reflns_number_total 963 Count of symmetry unique reflns 841 Completeness (_total/calc) 114.51% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 122 Fraction of Friedel pairs measured 0.145 Are heavy atom types Z>Si present no ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.

L-ornithine nitrate top
Crystal data top
C5H13N2O2+·NO3F(000) = 208
Mr = 195.18Dx = 1.464 Mg m3
Dm = 1.438 Mg m3
Dm measured by flotation in a mixture of carbon tetrachloride and xylene
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 5.1944 (6) ÅCell parameters from 24 reflections
b = 7.803 (1) Åθ = 9.8–14.4°
c = 11.050 (1) ŵ = 0.13 mm1
β = 98.75 (1)°T = 293 K
V = 442.66 (9) Å3Needle, colorless
Z = 20.6 × 0.3 × 0.3 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
919 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 25.0°, θmin = 1.9°
ω–2/q scansh = 16
Absorption correction: ψ scan
(North et al., 1968)
k = 19
Tmin = 0.887, Tmax = 0.956l = 1313
1295 measured reflections3 standard reflections every 60 min
963 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.090 w = 1/[σ2(Fo2) + (0.06P)2 + 0.0457P]
where P = (Fo2 + 2Fc2)/3
S = 1.16(Δ/σ)max < 0.001
838 reflectionsΔρmax = 0.22 e Å3
119 parametersΔρmin = 0.24 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=3DkFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.64 (5)
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
xyzUiso*/Ueq
O1A0.2581 (3)0.1101 (3)0.41866 (14)0.0382 (5)
O1B0.6749 (3)0.1187 (3)0.50548 (16)0.0352 (5)
C10.4346 (4)0.1404 (3)0.5045 (2)0.0256 (5)
C20.3529 (4)0.2038 (3)0.62462 (19)0.0256 (5)
H20.50000.26170.67420.031*
N10.1297 (4)0.3251 (3)0.59711 (17)0.0273 (5)
H1A0.17740.41460.55570.041*
H1B0.08210.36110.66690.041*
H1C0.00370.27210.55230.041*
C30.2634 (5)0.0528 (3)0.6963 (2)0.0310 (6)
H3A0.18920.09680.76560.037*
H3B0.12730.00880.64400.037*
N20.5796 (4)0.3618 (3)0.82032 (19)0.0369 (5)
H2A0.51320.45600.84900.055*
H2B0.70470.32030.87660.055*
H2C0.64580.38740.75280.055*
C40.4809 (5)0.0708 (4)0.7427 (2)0.0341 (6)
H4A0.57620.10000.67660.041*
H4B0.60100.01680.80730.041*
C50.3714 (5)0.2318 (4)0.7912 (2)0.0339 (6)
H5A0.29710.20500.86430.041*
H5B0.23400.27720.73040.041*
N110.8877 (5)0.8459 (3)0.0809 (2)0.0454 (6)
O11.0196 (5)0.9042 (4)0.17461 (18)0.0695 (9)
O20.6487 (5)0.8499 (4)0.0688 (3)0.0658 (7)
O30.9906 (7)0.7785 (8)0.0018 (4)0.1055 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0318 (8)0.0549 (12)0.0287 (8)0.0065 (9)0.0075 (6)0.0079 (9)
O1B0.0259 (8)0.0356 (9)0.0464 (10)0.0022 (8)0.0126 (7)0.0069 (8)
C10.0264 (11)0.0225 (11)0.0290 (10)0.0017 (9)0.0075 (9)0.0011 (9)
C20.0256 (10)0.0238 (11)0.0277 (10)0.0037 (9)0.0044 (8)0.0018 (9)
N10.0272 (10)0.0248 (10)0.0307 (9)0.0019 (9)0.0071 (7)0.0000 (8)
C30.0334 (12)0.0314 (12)0.0300 (11)0.0038 (10)0.0101 (9)0.0022 (10)
N20.0432 (12)0.0340 (11)0.0337 (10)0.0055 (10)0.0066 (8)0.0048 (9)
C40.0345 (12)0.0318 (13)0.0356 (11)0.0038 (12)0.0045 (10)0.0039 (11)
C50.0383 (13)0.0322 (13)0.0326 (12)0.0038 (11)0.0104 (10)0.0029 (10)
N110.0526 (14)0.0534 (15)0.0331 (11)0.0146 (12)0.0156 (11)0.0062 (11)
O10.0846 (16)0.090 (2)0.0349 (10)0.0521 (17)0.0108 (10)0.0085 (13)
O20.0509 (13)0.0727 (17)0.0745 (16)0.0021 (12)0.0116 (11)0.0244 (13)
O30.0603 (13)0.194 (4)0.0663 (14)0.012 (2)0.0237 (11)0.060 (2)
Geometric parameters (Å, º) top
O1A—C11.238 (3)N2—C51.482 (3)
O1B—C11.258 (3)N2—H2A0.89
C1—C21.535 (3)N2—H2B0.89
C2—N11.492 (3)N2—H2C0.89
C2—C31.531 (3)C4—C51.510 (4)
C2—H20.98C4—H4A0.97
N1—H1A0.89C4—H4B0.97
N1—H1B0.89C5—H5A0.97
N1—H1C0.89C5—H5B0.97
C3—C41.514 (3)N11—O31.212 (4)
C3—H3A0.97N11—O21.229 (3)
C3—H3B0.97N11—O11.238 (3)
O1A—C1—O1B126.8 (2)C5—N2—H2A109.5
O1A—C1—C2117.02 (18)C5—N2—H2B109.5
O1B—C1—C2116.14 (19)H2A—N2—H2B109.5
N1—C2—C3107.80 (18)C5—N2—H2C109.5
N1—C2—C1109.69 (17)H2A—N2—H2C109.5
C3—C2—C1110.17 (19)H2B—N2—H2C109.5
N1—C2—H2109.7C5—C4—C3110.4 (2)
C3—C2—H2109.7C5—C4—H4A109.6
C1—C2—H2109.7C3—C4—H4A109.6
C2—N1—H1A109.5C5—C4—H4B109.6
C2—N1—H1B109.5C3—C4—H4B109.6
H1A—N1—H1B109.5H4A—C4—H4B108.1
C2—N1—H1C109.5N2—C5—C4110.2 (2)
H1A—N1—H1C109.5N2—C5—H5A109.6
H1B—N1—H1C109.5C4—C5—H5A109.6
C4—C3—C2113.29 (19)N2—C5—H5B109.6
C4—C3—H3A108.9C4—C5—H5B109.6
C2—C3—H3A108.9H5A—C5—H5B108.1
C4—C3—H3B108.9O3—N11—O2118.8 (3)
C2—C3—H3B108.9O3—N11—O1120.9 (3)
H3A—C3—H3B107.7O2—N11—O1120.2 (3)
O1A—C1—C2—N139.2 (3)N1—C2—C3—C4173.54 (19)
O1B—C1—C2—N1143.3 (2)C1—C2—C3—C466.8 (2)
O1A—C1—C2—C379.3 (3)C2—C3—C4—C5169.4 (2)
O1B—C1—C2—C398.2 (2)C3—C4—C5—N2172.15 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1Bi0.891.932.813 (3)169
N1—H1B···O1ii0.891.932.818 (3)172
N1—H1C···O1Biii0.892.062.911 (3)161
N2—H2A···O2iv0.892.012.899 (4)173
N2—H2B···O3v0.892.022.911 (4)179
N2—H2C···O1Aii0.892.032.900 (3)165
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x+1, y1/2, z+1; (iii) x1, y, z; (iv) x+1, y3/2, z+1; (v) x, y1, z+1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds