In the title compound, C4H8N3O+·NO3-, creatininium cations and nitrate anions are linked to each other through strong hydrogen bonds, formed by all H atoms covalently bonded to the N atoms. Short contacts are also observed between the anions. This complex three-dimensional network of hydrogen bonds ensures the cohesion of the ionic structure.
Supporting information
CCDC reference: 263654
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.110
- Data-to-parameter ratio = 18.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1 .. O2 .. 2.62 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1 .. N .. 2.66 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: KappaCCD Server Software (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: ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
C4H8N3O+·NO3− | F(000) = 736 |
Mr = 176.14 | Dx = 1.604 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 12577 reflections |
a = 16.6509 (3) Å | θ = 5.8–30° |
b = 9.7336 (2) Å | µ = 0.14 mm−1 |
c = 8.9989 (3) Å | T = 293 K |
V = 1458.48 (6) Å3 | Needle, colourless |
Z = 8 | 0.30 × 0.10 × 0.10 mm |
Data collection top
Nonius KappaCCD area-detector diffractometer | 1473 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.057 |
Graphite monochromator | θmax = 30.0°, θmin = 5.8° |
φ scans | h = −23→23 |
12577 measured reflections | k = −13→11 |
2102 independent reflections | l = −12→12 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0578P)2 + 0.0648P] where P = (Fo2 + 2Fc2)/3 |
2102 reflections | (Δ/σ)max < 0.001 |
112 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.24 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 | Occ. (<1) |
O1 | 0.06746 (7) | 0.18948 (11) | −0.10346 (11) | 0.0443 (3) | |
O2 | 0.10363 (8) | −0.01131 (10) | −0.03021 (14) | 0.0524 (3) | |
O3 | 0.05801 (7) | 0.13520 (12) | 0.12800 (12) | 0.0494 (3) | |
C2 | 0.10771 (7) | 0.52246 (12) | 0.07062 (14) | 0.0267 (3) | |
C3 | 0.11659 (10) | 0.65477 (14) | −0.16217 (16) | 0.0391 (3) | |
H3A | 0.1463 | 0.6457 | −0.2531 | 0.059* | 0.50 |
H3B | 0.1298 | 0.7406 | −0.1156 | 0.059* | 0.50 |
H3C | 0.0601 | 0.6523 | −0.1834 | 0.059* | 0.50 |
H3D | 0.0778 | 0.7133 | −0.1150 | 0.059* | 0.50 |
H3E | 0.0943 | 0.6185 | −0.2524 | 0.059* | 0.50 |
H3F | 0.1640 | 0.7068 | −0.1847 | 0.059* | 0.50 |
C4 | 0.20032 (7) | 0.44373 (14) | −0.09326 (15) | 0.0329 (3) | |
H4A | 0.2518 | 0.4889 | −0.1053 | 0.039* | |
H4B | 0.1886 | 0.3904 | −0.1817 | 0.039* | |
C5 | 0.19931 (8) | 0.35450 (13) | 0.04404 (16) | 0.0329 (3) | |
N | 0.07619 (6) | 0.10309 (11) | −0.00027 (12) | 0.0305 (3) | |
N1 | 0.14425 (7) | 0.41399 (11) | 0.13818 (13) | 0.0318 (3) | |
H1 | 0.1263 (10) | 0.3780 (16) | 0.2202 (19) | 0.038* | |
N2 | 0.05025 (7) | 0.59258 (13) | 0.13514 (14) | 0.0384 (3) | |
H2A | 0.0277 | 0.6597 | 0.0890 | 0.046* | |
H2B | 0.0351 | 0.5715 | 0.2236 | 0.046* | |
N3 | 0.13706 (6) | 0.54265 (11) | −0.06321 (12) | 0.0284 (2) | |
O5 | 0.23793 (6) | 0.25261 (10) | 0.07035 (14) | 0.0491 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0547 (7) | 0.0463 (6) | 0.0321 (5) | 0.0103 (5) | 0.0043 (4) | 0.0081 (5) |
O2 | 0.0652 (8) | 0.0368 (6) | 0.0551 (7) | 0.0091 (5) | 0.0111 (6) | 0.0012 (5) |
O3 | 0.0587 (7) | 0.0606 (7) | 0.0287 (6) | −0.0118 (5) | 0.0144 (5) | −0.0077 (5) |
C2 | 0.0273 (5) | 0.0265 (6) | 0.0264 (6) | −0.0041 (5) | 0.0003 (4) | −0.0054 (5) |
C3 | 0.0478 (8) | 0.0364 (7) | 0.0330 (7) | 0.0000 (6) | −0.0012 (6) | 0.0064 (6) |
C4 | 0.0299 (6) | 0.0360 (7) | 0.0327 (7) | 0.0009 (5) | 0.0076 (5) | −0.0012 (5) |
C5 | 0.0294 (6) | 0.0337 (6) | 0.0357 (7) | 0.0003 (5) | 0.0004 (5) | −0.0010 (6) |
N | 0.0291 (5) | 0.0364 (6) | 0.0260 (6) | −0.0036 (4) | 0.0044 (4) | −0.0002 (4) |
N1 | 0.0379 (6) | 0.0320 (6) | 0.0253 (5) | 0.0003 (4) | 0.0036 (4) | 0.0020 (5) |
N2 | 0.0425 (6) | 0.0406 (6) | 0.0323 (6) | 0.0067 (5) | 0.0079 (5) | −0.0052 (5) |
N3 | 0.0311 (5) | 0.0288 (5) | 0.0253 (5) | −0.0001 (4) | 0.0027 (4) | 0.0007 (4) |
O5 | 0.0432 (6) | 0.0446 (6) | 0.0596 (7) | 0.0140 (5) | 0.0024 (5) | 0.0071 (5) |
Geometric parameters (Å, º) top
O1—N | 1.2612 (14) | C3—H3E | 0.9600 |
O2—N | 1.2334 (14) | C3—H3F | 0.9600 |
O3—N | 1.2336 (14) | C4—N3 | 1.4526 (16) |
C2—N2 | 1.3109 (16) | C4—C5 | 1.5104 (19) |
C2—N3 | 1.3144 (16) | C4—H4A | 0.9700 |
C2—N1 | 1.3618 (16) | C4—H4B | 0.9700 |
C3—N3 | 1.4492 (17) | C5—O5 | 1.2054 (15) |
C3—H3A | 0.9600 | C5—N1 | 1.3760 (17) |
C3—H3B | 0.9600 | N1—H1 | 0.870 (17) |
C3—H3C | 0.9600 | N2—H2A | 0.8600 |
C3—H3D | 0.9600 | N2—H2B | 0.8600 |
| | | |
N2—C2—N3 | 126.82 (12) | H3E—C3—H3F | 109.5 |
N2—C2—N1 | 122.14 (12) | N3—C4—C5 | 102.76 (10) |
N3—C2—N1 | 111.03 (11) | N3—C4—H4A | 111.2 |
N3—C3—H3A | 109.5 | C5—C4—H4A | 111.2 |
N3—C3—H3B | 109.5 | N3—C4—H4B | 111.2 |
H3A—C3—H3B | 109.5 | C5—C4—H4B | 111.2 |
N3—C3—H3C | 109.5 | H4A—C4—H4B | 109.1 |
H3A—C3—H3C | 109.5 | O5—C5—N1 | 125.50 (13) |
H3B—C3—H3C | 109.5 | O5—C5—C4 | 128.89 (13) |
N3—C3—H3D | 109.5 | N1—C5—C4 | 105.61 (11) |
H3A—C3—H3D | 141.1 | O2—N—O3 | 121.60 (12) |
H3B—C3—H3D | 56.3 | O2—N—O1 | 118.94 (11) |
H3C—C3—H3D | 56.3 | O3—N—O1 | 119.45 (12) |
N3—C3—H3E | 109.5 | C2—N1—C5 | 110.43 (11) |
H3A—C3—H3E | 56.3 | C2—N1—H1 | 122.5 (10) |
H3B—C3—H3E | 141.1 | C5—N1—H1 | 125.6 (10) |
H3C—C3—H3E | 56.3 | C2—N2—H2A | 120.0 |
H3D—C3—H3E | 109.5 | C2—N2—H2B | 120.0 |
N3—C3—H3F | 109.5 | H2A—N2—H2B | 120.0 |
H3A—C3—H3F | 56.3 | C2—N3—C3 | 126.03 (11) |
H3B—C3—H3F | 56.3 | C2—N3—C4 | 109.94 (10) |
H3C—C3—H3F | 141.1 | C3—N3—C4 | 123.73 (11) |
H3D—C3—H3F | 109.5 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.870 (17) | 1.977 (18) | 2.8381 (16) | 170.1 (15) |
N1—H1···O2i | 0.870 (17) | 2.621 (16) | 3.2031 (17) | 125.3 (12) |
N1—H1···Ni | 0.870 (17) | 2.657 (17) | 3.4493 (15) | 152.1 (13) |
N2—H2A···O1ii | 0.86 | 2.16 | 2.9022 (16) | 144 |
N2—H2B···O3iii | 0.86 | 2.14 | 2.8222 (16) | 136 |
N2—H2B···O2i | 0.86 | 2.56 | 3.2380 (19) | 136 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, −y+1, −z; (iii) −x, y+1/2, −z+1/2. |