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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
CCDC reference: 193735
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
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).
Crystal data top
C6H11N3O22+·2NO3− | F(000) = 584.39 |
Mr = 281.20 | Dx = 1.611 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 8658 reflections |
a = 5.4810 (2) Å | θ = 1.6–26.4° |
b = 8.2860 (5) Å | µ = 0.15 mm−1 |
c = 25.5350 (1) Å | T = 293 K |
V = 1159.69 (8) Å3 | Needle, colorless |
Z = 4 | 0.4 × 0.2 × 0.1 mm |
Data collection top
Nonius KappaCCD diffractometer | 1186 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.054 |
Graphite monochromator | θmax = 26.4°, θmin = 1.6° |
φ scans | h = −6→6 |
8658 measured reflections | k = −9→10 |
1286 independent reflections | l = −28→31 |
Refinement top
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H-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 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.1369 (5) | 0.2147 (3) | 0.06582 (10) | 0.0413 (6) | |
C2 | 0.2991 (5) | 0.3515 (3) | 0.08398 (9) | 0.0367 (5) | |
H2 | 0.4687 | 0.3141 | 0.0847 | 0.044* | |
C3 | 0.2266 (5) | 0.4075 (3) | 0.13888 (9) | 0.0441 (6) | |
H3 | 0.0568 | 0.4405 | 0.1383 | 0.053* | |
H3' | 0.2403 | 0.3169 | 0.1627 | 0.053* | |
C4 | 0.3760 (5) | 0.5431 (3) | 0.15945 (8) | 0.0371 (5) | |
C6 | 0.6786 (6) | 0.6688 (3) | 0.19920 (10) | 0.0514 (7) | |
H6 | 0.8198 | 0.6887 | 0.2183 | 0.062* | |
C5 | 0.3488 (6) | 0.7038 (3) | 0.15433 (10) | 0.0477 (6) | |
H5 | 0.2214 | 0.7556 | 0.1371 | 0.057* | |
N1 | 0.2764 (4) | 0.4850 (2) | 0.04518 (7) | 0.0397 (5) | |
H3N1 | 0.3032 | 0.4467 | 0.0131 | 0.060* | |
H2N1 | 0.3856 | 0.5613 | 0.0524 | 0.060* | |
H1N1 | 0.1270 | 0.5267 | 0.0468 | 0.060* | |
N2 | 0.5858 (4) | 0.5227 (3) | 0.18842 (7) | 0.0438 (5) | |
H1N2 | 0.6469 | 0.4317 | 0.1980 | 0.053* | |
N3 | 0.5389 (5) | 0.7774 (3) | 0.17855 (9) | 0.0550 (7) | |
H1N3 | 0.5628 | 0.8799 | 0.1800 | 0.066* | |
N4 | 0.7818 (4) | 0.7487 (3) | 0.05698 (8) | 0.0431 (5) | |
N5 | 0.7913 (5) | 0.1268 (3) | 0.20650 (9) | 0.0509 (6) | |
O1 | 0.1698 (6) | 0.0859 (2) | 0.09366 (10) | 0.0888 (10) | |
H1 | 0.0791 | 0.0141 | 0.0832 | 0.133* | |
O2 | −0.0073 (4) | 0.2273 (2) | 0.03089 (7) | 0.0536 (5) | |
O3 | 0.7709 (4) | 0.5988 (2) | 0.06161 (8) | 0.0580 (5) | |
O4 | 0.5985 (5) | 0.8287 (3) | 0.04941 (9) | 0.0765 (8) | |
O5 | 0.9865 (4) | 0.8132 (3) | 0.05967 (10) | 0.0684 (7) | |
O6 | 0.6101 (5) | 0.1164 (3) | 0.17807 (11) | 0.0849 (9) | |
O7 | 0.8534 (4) | 0.2613 (2) | 0.22367 (8) | 0.0578 (6) | |
O8 | 0.9039 (5) | 0.0055 (3) | 0.21913 (11) | 0.0886 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0430 (14) | 0.0341 (12) | 0.0470 (12) | −0.0036 (10) | −0.0046 (11) | −0.0044 (10) |
C2 | 0.0340 (13) | 0.0324 (11) | 0.0437 (12) | −0.0043 (10) | −0.0013 (10) | −0.0033 (9) |
C3 | 0.0462 (16) | 0.0465 (13) | 0.0395 (12) | −0.0111 (12) | 0.0014 (11) | −0.0018 (10) |
C4 | 0.0417 (14) | 0.0390 (12) | 0.0307 (10) | −0.0006 (11) | −0.0012 (10) | −0.0028 (9) |
C6 | 0.0537 (17) | 0.0581 (16) | 0.0424 (13) | −0.0099 (14) | −0.0068 (12) | −0.0133 (12) |
C5 | 0.0569 (17) | 0.0395 (13) | 0.0467 (13) | 0.0019 (12) | −0.0051 (12) | −0.0039 (11) |
N1 | 0.0430 (13) | 0.0371 (10) | 0.0389 (9) | −0.0071 (9) | 0.0031 (8) | −0.0042 (8) |
N2 | 0.0481 (13) | 0.0445 (11) | 0.0389 (10) | 0.0034 (10) | −0.0046 (9) | 0.0001 (8) |
N3 | 0.0727 (18) | 0.0383 (11) | 0.0541 (13) | −0.0055 (12) | −0.0039 (13) | −0.0101 (10) |
N4 | 0.0403 (13) | 0.0460 (11) | 0.0429 (10) | −0.0016 (10) | −0.0001 (9) | 0.0014 (9) |
N5 | 0.0614 (16) | 0.0371 (11) | 0.0542 (12) | −0.0025 (11) | −0.0097 (12) | 0.0032 (10) |
O1 | 0.120 (2) | 0.0402 (11) | 0.1058 (18) | −0.0276 (13) | −0.0673 (18) | 0.0180 (11) |
O2 | 0.0605 (13) | 0.0431 (10) | 0.0573 (10) | −0.0117 (10) | −0.0231 (10) | −0.0006 (8) |
O3 | 0.0515 (13) | 0.0424 (10) | 0.0802 (13) | −0.0109 (9) | 0.0032 (11) | 0.0076 (10) |
O4 | 0.0617 (16) | 0.0956 (18) | 0.0724 (14) | 0.0309 (15) | 0.0023 (11) | 0.0190 (13) |
O5 | 0.0569 (14) | 0.0527 (11) | 0.0956 (17) | −0.0201 (11) | −0.0097 (13) | −0.0077 (12) |
O6 | 0.088 (2) | 0.0532 (12) | 0.1138 (19) | 0.0048 (13) | −0.0577 (17) | −0.0092 (13) |
O7 | 0.0743 (15) | 0.0362 (9) | 0.0627 (11) | −0.0078 (10) | −0.0138 (11) | −0.0017 (8) |
O8 | 0.101 (2) | 0.0389 (11) | 0.126 (2) | 0.0063 (13) | −0.0512 (18) | 0.0048 (12) |
Geometric parameters (Å, º) top
C1—O2 | 1.196 (3) | C6—N2 | 1.342 (3) |
C1—O1 | 1.295 (3) | C5—N3 | 1.356 (4) |
C1—C2 | 1.513 (3) | N4—O4 | 1.219 (3) |
C2—N1 | 1.490 (3) | N4—O5 | 1.244 (3) |
C2—C3 | 1.529 (3) | N4—O3 | 1.249 (3) |
C3—C4 | 1.486 (3) | N5—O8 | 1.223 (3) |
C4—C5 | 1.346 (3) | N5—O6 | 1.233 (3) |
C4—N2 | 1.378 (3) | N5—O7 | 1.245 (3) |
C6—N3 | 1.294 (4) | | |
| | | |
O2—C1—O1 | 125.0 (2) | N3—C6—N2 | 108.6 (2) |
O2—C1—C2 | 123.4 (2) | C4—C5—N3 | 108.4 (3) |
O1—C1—C2 | 111.5 (2) | C6—N2—C4 | 108.4 (2) |
N1—C2—C1 | 107.67 (18) | C6—N3—C5 | 109.1 (2) |
N1—C2—C3 | 111.25 (19) | O4—N4—O5 | 121.2 (2) |
C1—C2—C3 | 110.8 (2) | O4—N4—O3 | 121.1 (3) |
C4—C3—C2 | 114.2 (2) | O5—N4—O3 | 117.7 (2) |
C5—C4—N2 | 105.4 (2) | O8—N5—O6 | 120.3 (2) |
C5—C4—C3 | 130.7 (3) | O8—N5—O7 | 120.3 (2) |
N2—C4—C3 | 123.8 (2) | O6—N5—O7 | 119.3 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H3N1···O2i | 0.89 | 2.10 | 2.876 (3) | 145 |
N1—H2N1···O3 | 0.89 | 2.15 | 2.900 (3) | 142 |
N1—H2N1···O4 | 0.89 | 2.51 | 3.352 (4) | 159 |
N1—H2N1···N4 | 0.89 | 2.67 | 3.541 (3) | 166 |
N1—H1N1···O3ii | 0.89 | 2.08 | 2.957 (3) | 170 |
N1—H1N1···O5ii | 0.89 | 2.52 | 3.171 (3) | 131 |
N1—H1N1···N4ii | 0.89 | 2.65 | 3.495 (3) | 159 |
N2—H1N2···O7 | 0.86 | 1.93 | 2.767 (3) | 166 |
N2—H1N2···N5 | 0.86 | 2.66 | 3.499 (3) | 167 |
N3—H1N3···O6iii | 0.86 | 1.98 | 2.836 (3) | 176 |
N3—H1N3···O8iii | 0.86 | 2.36 | 2.940 (3) | 125 |
N3—H1N3···N5iii | 0.86 | 2.49 | 3.287 (3) | 154 |
O1—H1···O5iv | 0.82 | 1.84 | 2.621 (3) | 158 |
Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) x−1, y, z; (iii) x, y+1, z; (iv) x−1, y−1, z. |
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