Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C4H9N2O3+·NO3-, crystallizes with two asparaginium cations and two nitrate anions in the asymmetric unit. In both asparaginium residues, protonation take place at the carboxyl O atom cis to the amine group. Cation I exists in a trans conformation, whereas cation II exhibits a gauche I conformation. A straight head-to-tail sequence is observed for one of the asparaginium cations. The crystal structure is stabilized by inter- and intra­molecular hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805017496/bt6674sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805017496/bt6674Isup2.hkl
Contains datablock I

CCDC reference: 277202

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.058
  • wR factor = 0.189
  • Data-to-parameter ratio = 6.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N2
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.846 0.993 Tmin' and Tmax expected: 0.965 0.973 RR' = 0.858 Please check that your absorption correction is appropriate. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.86 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.17 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 417.50 Ang-3 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C4 H9 N3 O6 Atom count from _chemical_formula_moiety:C4 H9 N2 O2 REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 1474 Count of symmetry unique reflns 1484 Completeness (_total/calc) 99.33% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, (1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Bruker, 2000); software used to prepare material for publication: SHELXL97.

L-Asparaginium nitrate top
Crystal data top
C4H9NO3+NO3Z = 2
Mr = 195.14F(000) = 204
Triclinic, P1Dx = 1.552 Mg m3
Dm = 1.545 Mg m3
Dm measured by Flotation using a liquid mixture of xylene and CCl4
a = 5.357 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.232 (3) ÅCell parameters from 25 reflections
c = 10.172 (4) Åθ = 9.8–14.0°
α = 96.88 (3)°µ = 0.15 mm1
β = 104.47 (3)°T = 293 K
γ = 102.11 (3)°Block, colorless
V = 417.5 (3) Å30.24 × 0.21 × 0.19 mm
Data collection top
Nonius MACH3 sealed-tube
diffractometer
1358 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.057
Graphite monochromatorθmax = 25.0°, θmin = 2.1°
ω–2θ scansh = 16
Absorption correction: ψ scan
(North et al., 1968)
k = 99
Tmin = 0.846, Tmax = 0.993l = 1212
1988 measured reflections3 standard reflections every 60 min
1474 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.1565P)2 + 0.0806P]
where P = (Fo2 + 2Fc2)/3
1474 reflections(Δ/σ)max < 0.001
239 parametersΔρmax = 0.39 e Å3
3 restraintsΔρmin = 0.42 e Å3
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
O1A0.4194 (11)0.5897 (7)0.2028 (5)0.0559 (13)
O1B0.5712 (10)0.4086 (6)0.3287 (5)0.0463 (11)
H1B0.64960.39450.27020.069*
C110.4456 (11)0.5254 (7)0.3041 (6)0.0350 (12)
C120.3249 (10)0.5801 (7)0.4178 (5)0.0308 (11)
H120.13080.55040.37970.037*
N110.3933 (10)0.4922 (6)0.5355 (5)0.0376 (11)
H11A0.31790.38210.50850.056*
H11B0.33390.53300.60360.056*
H11C0.56930.50880.56540.056*
C130.4199 (13)0.7707 (7)0.4688 (6)0.0403 (13)
H13A0.36430.80000.55040.048*
H13B0.61280.80430.49430.048*
C140.3085 (12)0.8651 (7)0.3593 (6)0.0361 (12)
N120.4745 (12)0.9956 (7)0.3397 (7)0.0517 (14)
H12A0.41821.05510.28010.062*
H12B0.63961.02170.38650.062*
O1C0.0656 (9)0.8199 (5)0.2948 (5)0.0448 (10)
O2A1.2159 (9)0.0990 (6)0.0883 (5)0.0445 (10)
O2B0.8322 (8)0.0600 (5)0.1003 (4)0.0407 (10)
H2B0.92970.08700.16550.061*
C210.9722 (10)0.0451 (7)0.0484 (6)0.0317 (11)
C220.8178 (11)0.1016 (7)0.0781 (5)0.0327 (11)
H220.85960.04830.15860.039*
N210.5250 (8)0.0396 (6)0.0997 (5)0.0330 (10)
H21A0.47990.07290.11660.049*
H21B0.43730.07750.17110.049*
H21C0.48360.07720.02410.049*
C230.8961 (11)0.2915 (7)0.0711 (6)0.0347 (12)
H23A1.08840.33000.04810.042*
H23B0.82130.31770.16090.042*
C240.7988 (10)0.3838 (7)0.0352 (5)0.0326 (11)
N220.7249 (14)0.5211 (7)0.0108 (6)0.0539 (15)
H22A0.66440.57430.06890.065*
H22B0.73680.55850.06350.065*
O2C0.7869 (8)0.3224 (5)0.1410 (4)0.0404 (9)
N10.0736 (11)0.6568 (6)0.7532 (6)0.0426 (12)
O110.0424 (13)0.7235 (7)0.8224 (7)0.0675 (16)
O120.3269 (10)0.6938 (7)0.7840 (5)0.0546 (12)
O130.0453 (11)0.5465 (8)0.6486 (7)0.0731 (18)
N20.1374 (10)0.1223 (6)0.6035 (6)0.0416 (12)
O210.0278 (13)0.0039 (7)0.6398 (6)0.0695 (16)
O220.3511 (14)0.2098 (9)0.6821 (8)0.100 (3)
O230.0439 (10)0.1644 (7)0.4930 (5)0.0556 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.077 (3)0.070 (3)0.041 (2)0.039 (3)0.028 (2)0.027 (2)
O1B0.063 (3)0.052 (2)0.038 (2)0.030 (2)0.024 (2)0.0162 (18)
C110.034 (3)0.034 (3)0.035 (3)0.006 (2)0.007 (2)0.008 (2)
C120.024 (2)0.036 (3)0.031 (2)0.0072 (19)0.004 (2)0.0092 (19)
N110.046 (3)0.039 (2)0.035 (2)0.017 (2)0.016 (2)0.0141 (19)
C130.050 (3)0.035 (3)0.032 (3)0.012 (2)0.005 (2)0.007 (2)
C140.038 (3)0.034 (3)0.033 (3)0.010 (2)0.004 (2)0.008 (2)
N120.039 (3)0.051 (3)0.056 (3)0.003 (2)0.004 (2)0.027 (3)
O1C0.041 (2)0.044 (2)0.050 (2)0.0113 (18)0.0076 (19)0.0215 (19)
O2A0.032 (2)0.057 (3)0.046 (2)0.0069 (18)0.0113 (17)0.018 (2)
O2B0.034 (2)0.046 (2)0.042 (2)0.0066 (17)0.0075 (17)0.0209 (18)
C210.026 (2)0.036 (2)0.034 (3)0.009 (2)0.008 (2)0.008 (2)
C220.035 (3)0.036 (3)0.029 (2)0.008 (2)0.013 (2)0.008 (2)
N210.024 (2)0.040 (2)0.033 (2)0.0046 (17)0.0062 (17)0.0080 (19)
C230.035 (3)0.039 (3)0.032 (3)0.006 (2)0.012 (2)0.014 (2)
C240.029 (2)0.034 (2)0.030 (3)0.001 (2)0.004 (2)0.0083 (19)
N220.086 (5)0.042 (3)0.053 (3)0.025 (3)0.041 (3)0.021 (2)
O2C0.046 (2)0.044 (2)0.039 (2)0.0141 (17)0.0207 (18)0.0128 (16)
N10.051 (3)0.038 (2)0.045 (3)0.010 (2)0.023 (2)0.012 (2)
O110.084 (4)0.064 (3)0.079 (4)0.025 (3)0.059 (3)0.022 (3)
O120.042 (2)0.056 (3)0.057 (3)0.006 (2)0.008 (2)0.000 (2)
O130.040 (3)0.079 (4)0.078 (4)0.000 (3)0.007 (3)0.022 (3)
N20.039 (3)0.040 (2)0.041 (3)0.005 (2)0.005 (2)0.011 (2)
O210.073 (4)0.055 (3)0.069 (3)0.010 (3)0.015 (3)0.024 (3)
O220.068 (4)0.086 (4)0.097 (5)0.029 (3)0.043 (4)0.058 (4)
O230.050 (3)0.056 (3)0.047 (3)0.006 (2)0.008 (2)0.017 (2)
Geometric parameters (Å, º) top
O1A—C111.205 (8)C21—C221.526 (7)
O1B—C111.298 (8)C22—N211.494 (7)
O1B—H1B0.8200C22—C231.520 (8)
C11—C121.526 (8)C22—H220.9800
C12—N111.481 (7)N21—H21A0.8900
C12—C131.526 (8)N21—H21B0.8900
C12—H120.9800N21—H21C0.8900
N11—H11A0.8900C23—C241.506 (8)
N11—H11B0.8900C23—H23A0.9700
N11—H11C0.8900C23—H23B0.9700
C13—C141.507 (8)C24—O2C1.252 (7)
C13—H13A0.9700C24—N221.305 (8)
C13—H13B0.9700N22—H22A0.8600
C14—O1C1.254 (8)N22—H22B0.8600
C14—N121.313 (9)N1—O111.205 (7)
N12—H12A0.8600N1—O131.244 (8)
N12—H12B0.8600N1—O121.274 (8)
O2A—C211.230 (7)N2—O211.227 (7)
O2B—C211.275 (7)N2—O231.232 (7)
O2B—H2B0.8200N2—O221.236 (8)
C11—O1B—H1B109.5O2B—C21—C22115.4 (4)
O1A—C11—O1B125.9 (6)N21—C22—C23111.0 (5)
O1A—C11—C12120.0 (5)N21—C22—C21110.3 (4)
O1B—C11—C12114.1 (5)C23—C22—C21113.0 (4)
N11—C12—C11111.1 (4)N21—C22—H22107.4
N11—C12—C13109.4 (4)C23—C22—H22107.4
C11—C12—C13111.0 (5)C21—C22—H22107.4
N11—C12—H12108.4C22—N21—H21A109.5
C11—C12—H12108.4C22—N21—H21B109.5
C13—C12—H12108.4H21A—N21—H21B109.5
C12—N11—H11A109.5C22—N21—H21C109.5
C12—N11—H11B109.5H21A—N21—H21C109.5
H11A—N11—H11B109.5H21B—N21—H21C109.5
C12—N11—H11C109.5C24—C23—C22111.5 (4)
H11A—N11—H11C109.5C24—C23—H23A109.3
H11B—N11—H11C109.5C22—C23—H23A109.3
C14—C13—C12111.2 (4)C24—C23—H23B109.3
C14—C13—H13A109.4C22—C23—H23B109.3
C12—C13—H13A109.4H23A—C23—H23B108.0
C14—C13—H13B109.4O2C—C24—N22123.3 (5)
C12—C13—H13B109.4O2C—C24—C23118.3 (5)
H13A—C13—H13B108.0N22—C24—C23118.4 (5)
O1C—C14—N12123.4 (5)C24—N22—H22A120.0
O1C—C14—C13119.7 (5)C24—N22—H22B120.0
N12—C14—C13116.9 (5)H22A—N22—H22B120.0
C14—N12—H12A120.0O11—N1—O13122.4 (6)
C14—N12—H12B120.0O11—N1—O12121.7 (6)
H12A—N12—H12B120.0O13—N1—O12115.9 (5)
C21—O2B—H2B109.5O21—N2—O23122.9 (5)
O2A—C21—O2B126.1 (5)O21—N2—O22117.8 (6)
O2A—C21—C22118.5 (5)O23—N2—O22119.3 (5)
O1A—C11—C12—N11176.9 (6)O2A—C21—C22—N21173.3 (5)
O1B—C11—C12—N113.2 (7)O2B—C21—C22—N219.0 (6)
O1A—C11—C12—C1354.9 (7)O2A—C21—C22—C2348.3 (7)
O1B—C11—C12—C13125.2 (5)O2B—C21—C22—C23133.9 (5)
N11—C12—C13—C14168.9 (5)N21—C22—C23—C2453.5 (6)
C11—C12—C13—C1468.2 (6)C21—C22—C23—C2471.0 (6)
C12—C13—C14—O1C46.8 (8)C22—C23—C24—O2C32.7 (7)
C12—C13—C14—N12135.1 (6)C22—C23—C24—N22145.6 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1B—H1B···O2C0.821.762.570 (6)169
N11—H11A···O230.892.032.858 (7)155
N11—H11A···O220.892.392.908 (8)117
N11—H11B···O120.892.142.994 (7)159
N11—H11B···O130.892.212.951 (8)140
N11—H11C···O13i0.891.972.855 (8)175
N12—H12A···O2Aii0.862.092.903 (8)156
N12—H12B···O23iii0.862.172.998 (7)162
O2B—H2B···O1Civ0.821.692.490 (6)166
N21—H21A···O12v0.891.962.815 (7)161
N21—H21B···O22vi0.891.972.832 (8)162
N21—H21B···O21vi0.892.433.176 (8)141
N21—H21C···O2Avii0.892.072.887 (6)153
N21—H21C···O2C0.892.452.988 (6)120
N22—H22A···O1A0.862.132.921 (7)154
N22—H22B···O11viii0.862.233.014 (8)151
Symmetry codes: (i) x+1, y, z; (ii) x1, y+1, z; (iii) x+1, y+1, z; (iv) x+1, y1, z; (v) x, y1, z1; (vi) x, y, z1; (vii) x1, y, z; (viii) x+1, y, z1.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

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