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The title salt, L-HisH22+·2NO3-, contains two nitrate anions and one L-histidinium dication. The anions and cations are linked to each other through strong hydrogen bonds, formed by all H atoms covalently bonded to the N and O atoms of the L-histidinium dications. This three-dimensional complex network of hydrogen bonds ensures the cohesion of the ionic structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802011625/dn6035sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802011625/dn6035Isup2.hkl
Contains datablock I

CCDC reference: 193735

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.036
  • wR factor = 0.090
  • Data-to-parameter ratio = 7.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 26.35 From the CIF: _reflns_number_total 1286 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1411 Completeness (_total/calc) 91.14% Alert C: < 95% complete General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 26.35 From the CIF: _reflns_number_total 1286 Count of symmetry unique reflns 1411 Completeness (_total/calc) 91.14% 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.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: KappaCCD Reference Manual (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: RASTER3D (Merritt et al., 1997) and PLUTON (Spek, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
C6H11N3O22+·2NO3F(000) = 584.39
Mr = 281.20Dx = 1.611 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 8658 reflections
a = 5.4810 (2) Åθ = 1.6–26.4°
b = 8.2860 (5) ŵ = 0.15 mm1
c = 25.5350 (1) ÅT = 293 K
V = 1159.69 (8) Å3Needle, colorless
Z = 40.4 × 0.2 × 0.1 mm
Data collection top
Nonius KappaCCD
diffractometer
1186 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.054
Graphite monochromatorθmax = 26.4°, θmin = 1.6°
φ scansh = 66
8658 measured reflectionsk = 910
1286 independent reflectionsl = 2831
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0331P)2 + 0.3591P]
where P = (Fo2 + 2Fc2)/3
1286 reflections(Δ/σ)max < 0.001
174 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.14 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
C10.1369 (5)0.2147 (3)0.06582 (10)0.0413 (6)
C20.2991 (5)0.3515 (3)0.08398 (9)0.0367 (5)
H20.46870.31410.08470.044*
C30.2266 (5)0.4075 (3)0.13888 (9)0.0441 (6)
H30.05680.44050.13830.053*
H3'0.24030.31690.16270.053*
C40.3760 (5)0.5431 (3)0.15945 (8)0.0371 (5)
C60.6786 (6)0.6688 (3)0.19920 (10)0.0514 (7)
H60.81980.68870.21830.062*
C50.3488 (6)0.7038 (3)0.15433 (10)0.0477 (6)
H50.22140.75560.13710.057*
N10.2764 (4)0.4850 (2)0.04518 (7)0.0397 (5)
H3N10.30320.44670.01310.060*
H2N10.38560.56130.05240.060*
H1N10.12700.52670.04680.060*
N20.5858 (4)0.5227 (3)0.18842 (7)0.0438 (5)
H1N20.64690.43170.19800.053*
N30.5389 (5)0.7774 (3)0.17855 (9)0.0550 (7)
H1N30.56280.87990.18000.066*
N40.7818 (4)0.7487 (3)0.05698 (8)0.0431 (5)
N50.7913 (5)0.1268 (3)0.20650 (9)0.0509 (6)
O10.1698 (6)0.0859 (2)0.09366 (10)0.0888 (10)
H10.07910.01410.08320.133*
O20.0073 (4)0.2273 (2)0.03089 (7)0.0536 (5)
O30.7709 (4)0.5988 (2)0.06161 (8)0.0580 (5)
O40.5985 (5)0.8287 (3)0.04941 (9)0.0765 (8)
O50.9865 (4)0.8132 (3)0.05967 (10)0.0684 (7)
O60.6101 (5)0.1164 (3)0.17807 (11)0.0849 (9)
O70.8534 (4)0.2613 (2)0.22367 (8)0.0578 (6)
O80.9039 (5)0.0055 (3)0.21913 (11)0.0886 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0430 (14)0.0341 (12)0.0470 (12)0.0036 (10)0.0046 (11)0.0044 (10)
C20.0340 (13)0.0324 (11)0.0437 (12)0.0043 (10)0.0013 (10)0.0033 (9)
C30.0462 (16)0.0465 (13)0.0395 (12)0.0111 (12)0.0014 (11)0.0018 (10)
C40.0417 (14)0.0390 (12)0.0307 (10)0.0006 (11)0.0012 (10)0.0028 (9)
C60.0537 (17)0.0581 (16)0.0424 (13)0.0099 (14)0.0068 (12)0.0133 (12)
C50.0569 (17)0.0395 (13)0.0467 (13)0.0019 (12)0.0051 (12)0.0039 (11)
N10.0430 (13)0.0371 (10)0.0389 (9)0.0071 (9)0.0031 (8)0.0042 (8)
N20.0481 (13)0.0445 (11)0.0389 (10)0.0034 (10)0.0046 (9)0.0001 (8)
N30.0727 (18)0.0383 (11)0.0541 (13)0.0055 (12)0.0039 (13)0.0101 (10)
N40.0403 (13)0.0460 (11)0.0429 (10)0.0016 (10)0.0001 (9)0.0014 (9)
N50.0614 (16)0.0371 (11)0.0542 (12)0.0025 (11)0.0097 (12)0.0032 (10)
O10.120 (2)0.0402 (11)0.1058 (18)0.0276 (13)0.0673 (18)0.0180 (11)
O20.0605 (13)0.0431 (10)0.0573 (10)0.0117 (10)0.0231 (10)0.0006 (8)
O30.0515 (13)0.0424 (10)0.0802 (13)0.0109 (9)0.0032 (11)0.0076 (10)
O40.0617 (16)0.0956 (18)0.0724 (14)0.0309 (15)0.0023 (11)0.0190 (13)
O50.0569 (14)0.0527 (11)0.0956 (17)0.0201 (11)0.0097 (13)0.0077 (12)
O60.088 (2)0.0532 (12)0.1138 (19)0.0048 (13)0.0577 (17)0.0092 (13)
O70.0743 (15)0.0362 (9)0.0627 (11)0.0078 (10)0.0138 (11)0.0017 (8)
O80.101 (2)0.0389 (11)0.126 (2)0.0063 (13)0.0512 (18)0.0048 (12)
Geometric parameters (Å, º) top
C1—O21.196 (3)C6—N21.342 (3)
C1—O11.295 (3)C5—N31.356 (4)
C1—C21.513 (3)N4—O41.219 (3)
C2—N11.490 (3)N4—O51.244 (3)
C2—C31.529 (3)N4—O31.249 (3)
C3—C41.486 (3)N5—O81.223 (3)
C4—C51.346 (3)N5—O61.233 (3)
C4—N21.378 (3)N5—O71.245 (3)
C6—N31.294 (4)
O2—C1—O1125.0 (2)N3—C6—N2108.6 (2)
O2—C1—C2123.4 (2)C4—C5—N3108.4 (3)
O1—C1—C2111.5 (2)C6—N2—C4108.4 (2)
N1—C2—C1107.67 (18)C6—N3—C5109.1 (2)
N1—C2—C3111.25 (19)O4—N4—O5121.2 (2)
C1—C2—C3110.8 (2)O4—N4—O3121.1 (3)
C4—C3—C2114.2 (2)O5—N4—O3117.7 (2)
C5—C4—N2105.4 (2)O8—N5—O6120.3 (2)
C5—C4—C3130.7 (3)O8—N5—O7120.3 (2)
N2—C4—C3123.8 (2)O6—N5—O7119.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H3N1···O2i0.892.102.876 (3)145
N1—H2N1···O30.892.152.900 (3)142
N1—H2N1···O40.892.513.352 (4)159
N1—H2N1···N40.892.673.541 (3)166
N1—H1N1···O3ii0.892.082.957 (3)170
N1—H1N1···O5ii0.892.523.171 (3)131
N1—H1N1···N4ii0.892.653.495 (3)159
N2—H1N2···O70.861.932.767 (3)166
N2—H1N2···N50.862.663.499 (3)167
N3—H1N3···O6iii0.861.982.836 (3)176
N3—H1N3···O8iii0.862.362.940 (3)125
N3—H1N3···N5iii0.862.493.287 (3)154
O1—H1···O5iv0.821.842.621 (3)158
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x1, y, z; (iii) x, y+1, z; (iv) x1, y1, z.
 

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