Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802008358/ci6124sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802008358/ci6124Isup2.hkl |
CCDC reference: 189384
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.037
- wR factor = 0.090
- Data-to-parameter ratio = 7.0
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
REFNR_01 Alert C Ratio of reflections to parameters is < 8 for a non-centrosymmetric structure, where ZMAX < 18 sine(theta)/lambda 0.5951 Proportion of unique data used 0.8702 Ratio reflections to parameters 7.0420 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.02 From the CIF: _reflns_number_total 963 Count of symmetry unique reflns 841 Completeness (_total/calc) 114.51% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 122 Fraction of Friedel pairs measured 0.145 Are heavy atom types Z>Si present no ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
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.
C5H13N2O2+·NO3− | F(000) = 208 |
Mr = 195.18 | Dx = 1.464 Mg m−3 Dm = 1.438 Mg m−3 Dm measured by flotation in a mixture of carbon tetrachloride and xylene |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.1944 (6) Å | Cell parameters from 24 reflections |
b = 7.803 (1) Å | θ = 9.8–14.4° |
c = 11.050 (1) Å | µ = 0.13 mm−1 |
β = 98.75 (1)° | T = 293 K |
V = 442.66 (9) Å3 | Needle, colorless |
Z = 2 | 0.6 × 0.3 × 0.3 mm |
Enraf-Nonius CAD-4 diffractometer | 919 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 25.0°, θmin = 1.9° |
ω–2/q scans | h = −1→6 |
Absorption correction: ψ scan (North et al., 1968) | k = −1→9 |
Tmin = 0.887, Tmax = 0.956 | l = −13→13 |
1295 measured reflections | 3 standard reflections every 60 min |
963 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.06P)2 + 0.0457P] where P = (Fo2 + 2Fc2)/3 |
S = 1.16 | (Δ/σ)max < 0.001 |
838 reflections | Δρmax = 0.22 e Å−3 |
119 parameters | Δρmin = −0.24 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=3DkFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.64 (5) |
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. |
x | y | z | Uiso*/Ueq | ||
O1A | 0.2581 (3) | 0.1101 (3) | 0.41866 (14) | 0.0382 (5) | |
O1B | 0.6749 (3) | 0.1187 (3) | 0.50548 (16) | 0.0352 (5) | |
C1 | 0.4346 (4) | 0.1404 (3) | 0.5045 (2) | 0.0256 (5) | |
C2 | 0.3529 (4) | 0.2038 (3) | 0.62462 (19) | 0.0256 (5) | |
H2 | 0.5000 | 0.2617 | 0.6742 | 0.031* | |
N1 | 0.1297 (4) | 0.3251 (3) | 0.59711 (17) | 0.0273 (5) | |
H1A | 0.1774 | 0.4146 | 0.5557 | 0.041* | |
H1B | 0.0821 | 0.3611 | 0.6669 | 0.041* | |
H1C | −0.0037 | 0.2721 | 0.5523 | 0.041* | |
C3 | 0.2634 (5) | 0.0528 (3) | 0.6963 (2) | 0.0310 (6) | |
H3A | 0.1892 | 0.0968 | 0.7656 | 0.037* | |
H3B | 0.1273 | −0.0088 | 0.6440 | 0.037* | |
N2 | 0.5796 (4) | −0.3618 (3) | 0.82032 (19) | 0.0369 (5) | |
H2A | 0.5132 | −0.4560 | 0.8490 | 0.055* | |
H2B | 0.7047 | −0.3203 | 0.8766 | 0.055* | |
H2C | 0.6458 | −0.3874 | 0.7528 | 0.055* | |
C4 | 0.4809 (5) | −0.0708 (4) | 0.7427 (2) | 0.0341 (6) | |
H4A | 0.5762 | −0.1000 | 0.6766 | 0.041* | |
H4B | 0.6010 | −0.0168 | 0.8073 | 0.041* | |
C5 | 0.3714 (5) | −0.2318 (4) | 0.7912 (2) | 0.0339 (6) | |
H5A | 0.2971 | −0.2050 | 0.8643 | 0.041* | |
H5B | 0.2340 | −0.2772 | 0.7304 | 0.041* | |
N11 | 0.8877 (5) | 0.8459 (3) | 0.0809 (2) | 0.0454 (6) | |
O1 | 1.0196 (5) | 0.9042 (4) | 0.17461 (18) | 0.0695 (9) | |
O2 | 0.6487 (5) | 0.8499 (4) | 0.0688 (3) | 0.0658 (7) | |
O3 | 0.9906 (7) | 0.7785 (8) | 0.0018 (4) | 0.1055 (15) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0318 (8) | 0.0549 (12) | 0.0287 (8) | −0.0065 (9) | 0.0075 (6) | −0.0079 (9) |
O1B | 0.0259 (8) | 0.0356 (9) | 0.0464 (10) | 0.0022 (8) | 0.0126 (7) | −0.0069 (8) |
C1 | 0.0264 (11) | 0.0225 (11) | 0.0290 (10) | −0.0017 (9) | 0.0075 (9) | −0.0011 (9) |
C2 | 0.0256 (10) | 0.0238 (11) | 0.0277 (10) | 0.0037 (9) | 0.0044 (8) | −0.0018 (9) |
N1 | 0.0272 (10) | 0.0248 (10) | 0.0307 (9) | 0.0019 (9) | 0.0071 (7) | 0.0000 (8) |
C3 | 0.0334 (12) | 0.0314 (12) | 0.0300 (11) | 0.0038 (10) | 0.0101 (9) | 0.0022 (10) |
N2 | 0.0432 (12) | 0.0340 (11) | 0.0337 (10) | 0.0055 (10) | 0.0066 (8) | 0.0048 (9) |
C4 | 0.0345 (12) | 0.0318 (13) | 0.0356 (11) | 0.0038 (12) | 0.0045 (10) | 0.0039 (11) |
C5 | 0.0383 (13) | 0.0322 (13) | 0.0326 (12) | 0.0038 (11) | 0.0104 (10) | 0.0029 (10) |
N11 | 0.0526 (14) | 0.0534 (15) | 0.0331 (11) | −0.0146 (12) | 0.0156 (11) | −0.0062 (11) |
O1 | 0.0846 (16) | 0.090 (2) | 0.0349 (10) | −0.0521 (17) | 0.0108 (10) | −0.0085 (13) |
O2 | 0.0509 (13) | 0.0727 (17) | 0.0745 (16) | 0.0021 (12) | 0.0116 (11) | −0.0244 (13) |
O3 | 0.0603 (13) | 0.194 (4) | 0.0663 (14) | −0.012 (2) | 0.0237 (11) | −0.060 (2) |
O1A—C1 | 1.238 (3) | N2—C5 | 1.482 (3) |
O1B—C1 | 1.258 (3) | N2—H2A | 0.89 |
C1—C2 | 1.535 (3) | N2—H2B | 0.89 |
C2—N1 | 1.492 (3) | N2—H2C | 0.89 |
C2—C3 | 1.531 (3) | C4—C5 | 1.510 (4) |
C2—H2 | 0.98 | C4—H4A | 0.97 |
N1—H1A | 0.89 | C4—H4B | 0.97 |
N1—H1B | 0.89 | C5—H5A | 0.97 |
N1—H1C | 0.89 | C5—H5B | 0.97 |
C3—C4 | 1.514 (3) | N11—O3 | 1.212 (4) |
C3—H3A | 0.97 | N11—O2 | 1.229 (3) |
C3—H3B | 0.97 | N11—O1 | 1.238 (3) |
O1A—C1—O1B | 126.8 (2) | C5—N2—H2A | 109.5 |
O1A—C1—C2 | 117.02 (18) | C5—N2—H2B | 109.5 |
O1B—C1—C2 | 116.14 (19) | H2A—N2—H2B | 109.5 |
N1—C2—C3 | 107.80 (18) | C5—N2—H2C | 109.5 |
N1—C2—C1 | 109.69 (17) | H2A—N2—H2C | 109.5 |
C3—C2—C1 | 110.17 (19) | H2B—N2—H2C | 109.5 |
N1—C2—H2 | 109.7 | C5—C4—C3 | 110.4 (2) |
C3—C2—H2 | 109.7 | C5—C4—H4A | 109.6 |
C1—C2—H2 | 109.7 | C3—C4—H4A | 109.6 |
C2—N1—H1A | 109.5 | C5—C4—H4B | 109.6 |
C2—N1—H1B | 109.5 | C3—C4—H4B | 109.6 |
H1A—N1—H1B | 109.5 | H4A—C4—H4B | 108.1 |
C2—N1—H1C | 109.5 | N2—C5—C4 | 110.2 (2) |
H1A—N1—H1C | 109.5 | N2—C5—H5A | 109.6 |
H1B—N1—H1C | 109.5 | C4—C5—H5A | 109.6 |
C4—C3—C2 | 113.29 (19) | N2—C5—H5B | 109.6 |
C4—C3—H3A | 108.9 | C4—C5—H5B | 109.6 |
C2—C3—H3A | 108.9 | H5A—C5—H5B | 108.1 |
C4—C3—H3B | 108.9 | O3—N11—O2 | 118.8 (3) |
C2—C3—H3B | 108.9 | O3—N11—O1 | 120.9 (3) |
H3A—C3—H3B | 107.7 | O2—N11—O1 | 120.2 (3) |
O1A—C1—C2—N1 | −39.2 (3) | N1—C2—C3—C4 | −173.54 (19) |
O1B—C1—C2—N1 | 143.3 (2) | C1—C2—C3—C4 | 66.8 (2) |
O1A—C1—C2—C3 | 79.3 (3) | C2—C3—C4—C5 | −169.4 (2) |
O1B—C1—C2—C3 | −98.2 (2) | C3—C4—C5—N2 | 172.15 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1Bi | 0.89 | 1.93 | 2.813 (3) | 169 |
N1—H1B···O1ii | 0.89 | 1.93 | 2.818 (3) | 172 |
N1—H1C···O1Biii | 0.89 | 2.06 | 2.911 (3) | 161 |
N2—H2A···O2iv | 0.89 | 2.01 | 2.899 (4) | 173 |
N2—H2B···O3v | 0.89 | 2.02 | 2.911 (4) | 179 |
N2—H2C···O1Aii | 0.89 | 2.03 | 2.900 (3) | 165 |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+1, y−1/2, −z+1; (iii) x−1, y, z; (iv) −x+1, y−3/2, −z+1; (v) x, y−1, z+1. |