Download citation
Download citation
link to html
In the title compound, 2C5H9NO2·H+·NO3, the two proline residues are linked by a strong O—H...O hydrogen bond, with an O...O distance of 2.414 (3) Å. In one of the residues, the pyrrolidine ring adopts an envelope conformation, while in the other it adopts a half-chair conformation. N—H...O hydrogen bonds link the two residues to form double-chain structures down the a axis, which are interlinked by N—H...O hydrogen bonds involving the O atoms of the nitrate ions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802012394/ci6141sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802012394/ci6141Isup2.hkl
Contains datablock I

CCDC reference: 193750

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.047
  • wR factor = 0.121
  • Data-to-parameter ratio = 7.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.54 From the CIF: _reflns_number_total 1430 Count of symmetry unique reflns 1480 Completeness (_total/calc) 96.62% 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 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.

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.

Bis(L-proline) hydrogen nitrate top
Crystal data top
2C5H9NO2·H+·NO3Dx = 1.458 Mg m3
Dm = 1.454 Mg m3
Dm measured by flotation method in a mixture of carbon tetrachloride and xylene
Mr = 293.28Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 7.2006 (6) Åθ = 11.3–13.9°
b = 7.711 (1) ŵ = 0.12 mm1
c = 24.060 (3) ÅT = 293 K
V = 1335.9 (3) Å3Block, colourless
Z = 40.5 × 0.5 × 0.5 mm
F(000) = 624
Data collection top
Enraf-Nonis CAD-4
diffractometer
1276 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 25.5°, θmin = 1.7°
ω–2θ scansh = 18
Absorption correction: ψ scan
(North et al., 1968)
k = 19
Tmin = 0.916, Tmax = 0.937l = 2929
3718 measured reflections3 standard reflections every 60 min
1430 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)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.0703P)2 + 0.319P]
where P = (Fo2 + 2Fc2)/3
S = 1.16(Δ/σ)max < 0.001
1430 reflectionsΔρmax = 0.32 e Å3
186 parametersΔρmin = 0.29 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.102 (9)
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
O1A1.1931 (3)0.0793 (3)0.49046 (8)0.0446 (6)
O1B1.0311 (3)0.0038 (3)0.41810 (8)0.0450 (6)
C111.0476 (4)0.0425 (3)0.46762 (11)0.0316 (6)
C120.8657 (4)0.0524 (4)0.49757 (10)0.0324 (6)
H120.77940.12300.47570.039*
N110.8923 (4)0.1340 (3)0.55183 (9)0.0382 (6)
H11A1.00570.10880.56540.046*
H11B0.88160.25000.54900.046*
C130.7734 (5)0.1195 (4)0.51134 (13)0.0468 (8)
H13A0.86250.20290.52540.056*
H13B0.71080.16790.47920.056*
C140.6374 (5)0.0664 (5)0.55541 (14)0.0570 (9)
H14A0.60040.16480.57800.068*
H14B0.52750.01400.53920.068*
C150.7449 (5)0.0629 (5)0.58893 (12)0.0493 (8)
H15A0.80020.00730.62110.059*
H15B0.66390.15520.60170.059*
O2A0.5232 (3)0.0304 (3)0.40632 (9)0.0511 (6)
O2B0.2852 (3)0.0571 (5)0.35494 (9)0.0651 (8)
H2B0.200 (8)0.004 (7)0.389 (2)0.12 (2)*
C210.4573 (4)0.0281 (4)0.36512 (11)0.0375 (7)
C220.5786 (4)0.0743 (4)0.31718 (10)0.0359 (7)
H220.54740.19100.30410.043*
N210.7797 (3)0.0672 (4)0.33214 (10)0.0405 (6)
H21A0.82340.17550.33700.049*
H21B0.79410.00890.36430.049*
C230.5624 (5)0.0517 (6)0.26988 (13)0.0549 (9)
H23A0.46500.01750.24430.066*
H23B0.53730.16810.28330.066*
C240.7500 (5)0.0413 (8)0.24289 (15)0.0805 (15)
H24A0.77550.14640.22210.097*
H24B0.75530.05650.21760.097*
C250.8848 (5)0.0199 (6)0.28760 (14)0.0581 (10)
H25A0.98870.05080.27560.070*
H25B0.93130.13140.30000.070*
N0.7577 (5)0.4984 (4)0.35805 (13)0.0615 (9)
O10.6564 (5)0.3986 (5)0.38431 (13)0.0893 (11)
O20.8670 (4)0.4309 (5)0.32523 (12)0.0804 (9)
O30.7491 (9)0.6519 (4)0.36692 (17)0.139 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0324 (11)0.0601 (12)0.0411 (10)0.0096 (11)0.0011 (9)0.0074 (10)
O1B0.0301 (10)0.0690 (15)0.0358 (10)0.0006 (11)0.0019 (9)0.0107 (10)
C110.0300 (14)0.0301 (12)0.0348 (12)0.0012 (12)0.0002 (11)0.0001 (12)
C120.0288 (14)0.0364 (13)0.0320 (12)0.0000 (12)0.0014 (11)0.0033 (12)
N110.0394 (14)0.0413 (12)0.0338 (11)0.0011 (12)0.0037 (10)0.0041 (11)
C130.0416 (18)0.0450 (15)0.0538 (17)0.0093 (15)0.0066 (16)0.0067 (14)
C140.0504 (19)0.062 (2)0.0592 (18)0.012 (2)0.0192 (17)0.0004 (17)
C150.0502 (18)0.0605 (18)0.0371 (14)0.0017 (18)0.0113 (14)0.0027 (15)
O2A0.0397 (11)0.0726 (15)0.0409 (11)0.0038 (13)0.0020 (9)0.0184 (12)
O2B0.0304 (11)0.123 (2)0.0424 (11)0.0053 (16)0.0035 (10)0.0200 (14)
C210.0327 (14)0.0479 (16)0.0320 (13)0.0007 (14)0.0001 (12)0.0048 (13)
C220.0287 (14)0.0478 (16)0.0311 (13)0.0025 (13)0.0024 (11)0.0008 (12)
N210.0317 (12)0.0567 (14)0.0332 (11)0.0005 (13)0.0024 (10)0.0013 (12)
C230.0444 (17)0.079 (2)0.0414 (15)0.0037 (19)0.0018 (14)0.0174 (18)
C240.049 (2)0.145 (4)0.0473 (17)0.000 (3)0.0097 (16)0.032 (2)
C250.0371 (16)0.089 (3)0.0479 (17)0.005 (2)0.0097 (14)0.0088 (19)
N0.066 (2)0.0639 (19)0.0543 (16)0.0107 (18)0.0078 (16)0.0059 (15)
O10.088 (2)0.095 (2)0.085 (2)0.018 (2)0.0345 (19)0.0282 (18)
O20.0669 (18)0.103 (2)0.0715 (17)0.0097 (19)0.0269 (16)0.0119 (17)
O30.228 (6)0.0598 (19)0.129 (3)0.027 (3)0.019 (4)0.006 (2)
Geometric parameters (Å, º) top
O1A—C111.216 (3)O2B—H2B1.11 (6)
O1B—C111.250 (3)C21—C221.490 (4)
C11—C121.497 (4)C22—N211.493 (4)
C12—N111.462 (3)C22—C231.501 (4)
C12—C131.519 (4)C22—H220.98
C12—H120.98N21—C251.474 (4)
N11—C151.491 (4)N21—H21A0.90
N11—H11A0.90N21—H21B0.90
N11—H11B0.90C23—C241.501 (5)
C13—C141.500 (5)C23—H23A0.97
C13—H13A0.97C23—H23B0.97
C13—H13B0.97C24—C251.458 (5)
C14—C151.498 (5)C24—H24A0.97
C14—H14A0.97C24—H24B0.97
C14—H14B0.97C25—H25A0.97
C15—H15A0.97C25—H25B0.97
C15—H15B0.97N—O31.204 (5)
O2A—C211.188 (4)N—O11.234 (5)
O2B—C211.282 (4)N—O21.231 (4)
O1A—C11—O1B125.4 (3)O2A—C21—C22120.2 (3)
O1A—C11—C12121.6 (2)O2B—C21—C22112.1 (2)
O1B—C11—C12113.0 (2)C21—C22—N21111.9 (2)
N11—C12—C11109.7 (2)C21—C22—C23112.8 (3)
N11—C12—C13103.8 (2)N21—C22—C23103.6 (2)
C11—C12—C13116.3 (2)C21—C22—H22109.5
N11—C12—H12108.9N21—C22—H22109.5
C11—C12—H12108.9C23—C22—H22109.5
C13—C12—H12108.9C25—N21—C22109.8 (2)
C12—N11—C15106.4 (2)C25—N21—H21A109.7
C12—N11—H11A110.4C22—N21—H21A109.7
C15—N11—H11A110.4C25—N21—H21B109.7
C12—N11—H11B110.4C22—N21—H21B109.7
C15—N11—H11B110.4H21A—N21—H21B108.2
H11A—N11—H11B108.6C22—C23—C24102.9 (3)
C14—C13—C12101.6 (2)C22—C23—H23A111.2
C14—C13—H13A111.4C24—C23—H23A111.2
C12—C13—H13A111.4C22—C23—H23B111.2
C14—C13—H13B111.4C24—C23—H23B111.2
C12—C13—H13B111.4H23A—C23—H23B109.1
H13A—C13—H13B109.3C25—C24—C23106.6 (3)
C15—C14—C13103.0 (3)C25—C24—H24A110.4
C15—C14—H14A111.2C23—C24—H24A110.4
C13—C14—H14A111.2C25—C24—H24B110.4
C15—C14—H14B111.2C23—C24—H24B110.4
C13—C14—H14B111.2H24A—C24—H24B108.6
H14A—C14—H14B109.1C24—C25—N21104.3 (3)
N11—C15—C14106.9 (2)C24—C25—H25A110.9
N11—C15—H15A110.3N21—C25—H25A110.9
C14—C15—H15A110.3C24—C25—H25B110.9
N11—C15—H15B110.3N21—C25—H25B110.9
C14—C15—H15B110.3H25A—C25—H25B108.9
H15A—C15—H15B108.6O3—N—O1119.4 (4)
C21—O2B—H2B109 (3)O3—N—O2124.2 (5)
O2A—C21—O2B127.7 (3)O1—N—O2116.3 (3)
O1A—C11—C12—N118.3 (4)O2A—C21—C22—N2110.0 (5)
O1B—C11—C12—N11170.7 (2)O2B—C21—C22—N21170.9 (3)
O1A—C11—C12—C13109.1 (3)O2A—C21—C22—C23106.3 (3)
O1B—C11—C12—C1371.9 (3)O2B—C21—C22—C2372.8 (4)
C11—C12—N11—C15151.9 (2)C21—C22—N21—C25136.1 (3)
C13—C12—N11—C1527.0 (3)C23—C22—N21—C2514.3 (4)
N11—C12—C13—C1441.6 (3)C21—C22—C23—C24151.4 (3)
C11—C12—C13—C14162.2 (2)N21—C22—C23—C2430.2 (4)
C12—C13—C14—C1539.7 (3)C22—C23—C24—C2536.8 (5)
C12—N11—C15—C142.1 (3)C23—C24—C25—N2127.7 (5)
C13—C14—C15—N1123.9 (4)C22—N21—C25—C248.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2B—H2B···O1Bi1.11 (6)1.40 (6)2.414 (3)148 (5)
N11—H11A···O1ii0.902.303.045 (4)141
N11—H11A···O3ii0.902.423.231 (6)151
N11—H11B···O1Aiii0.902.122.825 (3)135
N11—H11B···O2Aiv0.902.252.932 (3)132
N21—H21B···O2A0.902.222.676 (3)111
N21—H21B···O1B0.902.142.792 (3)128
N21—H21A···O20.902.012.879 (5)161
N21—H21A···O10.902.392.982 (4)124
Symmetry codes: (i) x1, y, z; (ii) x+1/2, y+1/2, z+1; (iii) x1/2, y1/2, z+1; (iv) x+1/2, y1/2, 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