Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806055693/er2017sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806055693/er2017Isup2.hkl |
CCDC reference: 636252
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.122
- Data-to-parameter ratio = 23.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N6
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 34.21 From the CIF: _reflns_number_total 4939 From the CIF: _diffrn_reflns_limit_ max hkl 31. 5. 30. From the CIF: _diffrn_reflns_limit_ min hkl -31. -5. -28. TEST1: Expected hkl limits for theta max Calculated maximum hkl 34. 5. 30. Calculated minimum hkl -34. -5. -30.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2003) and WinGX (Farrugia, 1999).
C5H7N2+·NO3− | F(000) = 656 |
Mr = 157.14 | Dx = 1.513 Mg m−3 |
Monoclinic, P2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yc | Cell parameters from 948 reflections |
a = 21.5559 (11) Å | θ = 2–30° |
b = 3.6473 (1) Å | µ = 0.13 mm−1 |
c = 19.4851 (8) Å | T = 120 K |
β = 115.752 (4)° | Needle, colourless |
V = 1379.79 (10) Å3 | 0.40 × 0.20 × 0.15 mm |
Z = 8 |
Oxford Excalibur2 diffractometer | 4939 independent reflections |
Radiation source: fine-focus sealed tube | 3460 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
Detector resolution: 10 pixels mm-1 | θmax = 34.2°, θmin = 4.2° |
ω/2θ scans | h = −31→31 |
Absorption correction: multi-scan (Blessing, 1995) | k = −5→5 |
Tmin = 0.949, Tmax = 0.983 | l = −28→30 |
20896 measured reflections |
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) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0641P)2 + 0.2988P] where P = (Fo2 + 2Fc2)/3 |
4939 reflections | (Δ/σ)max < 0.001 |
207 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
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 | ||
N2 | 0.21685 (5) | 0.7605 (3) | 0.44255 (5) | 0.0232 (2) | |
H2A | 0.2132 | 0.6850 | 0.3991 | 0.028* | |
H2B | 0.2556 | 0.7433 | 0.4823 | 0.028* | |
N4 | 0.28548 (5) | 0.2903 (3) | 0.22943 (6) | 0.0261 (2) | |
H4A | 0.2901 | 0.3560 | 0.1895 | 0.031* | |
H4B | 0.2465 | 0.3174 | 0.2311 | 0.031* | |
H3A | 0.4017 (8) | 0.195 (4) | 0.2444 (9) | 0.031 (4)* | |
H1A | 0.1000 (8) | 0.839 (5) | 0.3399 (9) | 0.034 (4)* | |
O5 | 0.07779 (4) | 0.5833 (3) | 0.24849 (5) | 0.0280 (2) | |
N1 | 0.10231 (5) | 0.9280 (3) | 0.38510 (5) | 0.01788 (18) | |
N6 | 0.12834 (5) | 0.4795 (3) | 0.23775 (5) | 0.02012 (19) | |
C5 | 0.16261 (6) | 0.9039 (3) | 0.44829 (6) | 0.0176 (2) | |
O6 | 0.12076 (5) | 0.3578 (3) | 0.17551 (5) | 0.0291 (2) | |
C2 | 0.04407 (6) | 1.1934 (3) | 0.45110 (6) | 0.0217 (2) | |
H2 | 0.0043 | 1.2898 | 0.4516 | 0.026* | |
C3 | 0.10593 (6) | 1.1731 (3) | 0.51847 (6) | 0.0220 (2) | |
H3 | 0.1070 | 1.2551 | 0.5641 | 0.026* | |
C4 | 0.16429 (6) | 1.0348 (3) | 0.51749 (6) | 0.0209 (2) | |
H4 | 0.2050 | 1.0264 | 0.5621 | 0.025* | |
C1 | 0.04402 (6) | 1.0682 (3) | 0.38525 (6) | 0.0208 (2) | |
H1 | 0.0038 | 1.0789 | 0.3401 | 0.025* | |
O4 | 0.18725 (5) | 0.5006 (4) | 0.29127 (6) | 0.0528 (4) | |
N3 | 0.39917 (5) | 0.1076 (3) | 0.28445 (5) | 0.01796 (18) | |
C10 | 0.33863 (6) | 0.1468 (3) | 0.28865 (6) | 0.0184 (2) | |
C9 | 0.33569 (6) | 0.0333 (3) | 0.35649 (7) | 0.0229 (2) | |
H9 | 0.2951 | 0.0597 | 0.3619 | 0.027* | |
C7 | 0.45429 (6) | −0.1560 (3) | 0.40664 (6) | 0.0230 (2) | |
H7 | 0.4930 | −0.2599 | 0.4456 | 0.028* | |
C8 | 0.39264 (7) | −0.1154 (3) | 0.41411 (6) | 0.0240 (2) | |
H8 | 0.3906 | −0.1904 | 0.4587 | 0.029* | |
C6 | 0.45608 (6) | −0.0401 (3) | 0.34132 (6) | 0.0209 (2) | |
H6 | 0.4965 | −0.0621 | 0.3355 | 0.025* | |
O1 | 0.37945 (5) | 0.6265 (3) | 0.05292 (5) | 0.0315 (2) | |
O2 | 0.42056 (4) | 0.5031 (3) | 0.17353 (5) | 0.0272 (2) | |
N5 | 0.37156 (5) | 0.5033 (3) | 0.10757 (5) | 0.0212 (2) | |
O3 | 0.31433 (5) | 0.3739 (3) | 0.09833 (5) | 0.0344 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N2 | 0.0203 (4) | 0.0300 (5) | 0.0186 (4) | 0.0041 (4) | 0.0078 (3) | −0.0005 (4) |
N4 | 0.0211 (4) | 0.0355 (6) | 0.0233 (4) | 0.0050 (4) | 0.0111 (4) | 0.0035 (4) |
O5 | 0.0189 (4) | 0.0422 (5) | 0.0222 (4) | 0.0042 (4) | 0.0082 (3) | −0.0067 (4) |
N1 | 0.0197 (4) | 0.0198 (4) | 0.0140 (4) | −0.0015 (4) | 0.0072 (3) | −0.0002 (3) |
N6 | 0.0204 (4) | 0.0239 (5) | 0.0174 (4) | 0.0013 (4) | 0.0093 (3) | −0.0004 (3) |
C5 | 0.0196 (5) | 0.0167 (4) | 0.0161 (4) | −0.0007 (4) | 0.0073 (4) | 0.0015 (4) |
O6 | 0.0339 (5) | 0.0371 (5) | 0.0187 (4) | 0.0002 (4) | 0.0137 (3) | −0.0055 (3) |
C2 | 0.0229 (5) | 0.0182 (5) | 0.0272 (5) | 0.0017 (4) | 0.0138 (4) | 0.0013 (4) |
C3 | 0.0300 (6) | 0.0194 (5) | 0.0194 (5) | −0.0004 (5) | 0.0133 (4) | −0.0021 (4) |
C4 | 0.0238 (5) | 0.0209 (5) | 0.0157 (4) | 0.0012 (4) | 0.0065 (4) | −0.0004 (4) |
C1 | 0.0185 (5) | 0.0206 (5) | 0.0217 (5) | 0.0003 (4) | 0.0072 (4) | 0.0020 (4) |
O4 | 0.0186 (4) | 0.1047 (11) | 0.0279 (5) | 0.0104 (5) | 0.0033 (4) | −0.0258 (6) |
N3 | 0.0190 (4) | 0.0204 (4) | 0.0166 (4) | −0.0013 (4) | 0.0097 (3) | −0.0016 (3) |
C10 | 0.0201 (5) | 0.0181 (5) | 0.0196 (4) | −0.0015 (4) | 0.0109 (4) | −0.0033 (4) |
C9 | 0.0253 (5) | 0.0251 (5) | 0.0238 (5) | −0.0024 (5) | 0.0160 (4) | −0.0012 (4) |
C7 | 0.0257 (5) | 0.0188 (5) | 0.0194 (5) | −0.0005 (4) | 0.0052 (4) | −0.0013 (4) |
C8 | 0.0337 (6) | 0.0221 (5) | 0.0186 (5) | −0.0040 (5) | 0.0135 (4) | −0.0009 (4) |
C6 | 0.0186 (5) | 0.0207 (5) | 0.0234 (5) | −0.0005 (4) | 0.0093 (4) | −0.0035 (4) |
O1 | 0.0376 (5) | 0.0402 (5) | 0.0216 (4) | −0.0024 (4) | 0.0176 (4) | 0.0044 (4) |
O2 | 0.0213 (4) | 0.0400 (5) | 0.0176 (4) | −0.0073 (4) | 0.0061 (3) | 0.0014 (3) |
N5 | 0.0228 (4) | 0.0250 (5) | 0.0171 (4) | −0.0017 (4) | 0.0098 (3) | −0.0015 (3) |
O3 | 0.0236 (4) | 0.0568 (6) | 0.0216 (4) | −0.0145 (4) | 0.0087 (3) | −0.0041 (4) |
N2—C5 | 1.3292 (14) | C3—H3 | 0.9300 |
N2—H2A | 0.8600 | C4—H4 | 0.9300 |
N2—H2B | 0.8600 | C1—H1 | 0.9300 |
N4—C10 | 1.3301 (15) | N3—C10 | 1.3503 (13) |
N4—H4A | 0.8600 | N3—C6 | 1.3571 (14) |
N4—H4B | 0.8600 | N3—H3A | 0.866 (16) |
O5—N6 | 1.2540 (12) | C10—C9 | 1.4125 (15) |
N1—C5 | 1.3501 (13) | C9—C8 | 1.3653 (17) |
N1—C1 | 1.3577 (14) | C9—H9 | 0.9300 |
N1—H1A | 0.920 (16) | C7—C6 | 1.3573 (16) |
N6—O6 | 1.2338 (12) | C7—C8 | 1.4061 (17) |
N6—O4 | 1.2470 (13) | C7—H7 | 0.9300 |
C5—C4 | 1.4159 (14) | C8—H8 | 0.9300 |
C2—C1 | 1.3616 (15) | C6—H6 | 0.9300 |
C2—C3 | 1.4092 (16) | O1—N5 | 1.2339 (12) |
C2—H2 | 0.9300 | O2—N5 | 1.2600 (12) |
C3—C4 | 1.3631 (16) | N5—O3 | 1.2585 (13) |
C5—N2—H2A | 120.0 | N1—C1—C2 | 120.44 (10) |
C5—N2—H2B | 120.0 | N1—C1—H1 | 119.8 |
H2A—N2—H2B | 120.0 | C2—C1—H1 | 119.8 |
C10—N4—H4A | 120.0 | C10—N3—C6 | 123.17 (9) |
C10—N4—H4B | 120.0 | C10—N3—H3A | 117.1 (11) |
H4A—N4—H4B | 120.0 | C6—N3—H3A | 119.6 (11) |
C5—N1—C1 | 123.21 (9) | N4—C10—N3 | 118.68 (9) |
C5—N1—H1A | 118.7 (10) | N4—C10—C9 | 123.73 (10) |
C1—N1—H1A | 118.1 (10) | N3—C10—C9 | 117.59 (10) |
O6—N6—O4 | 119.74 (10) | C8—C9—C10 | 119.75 (10) |
O6—N6—O5 | 121.26 (10) | C8—C9—H9 | 120.1 |
O4—N6—O5 | 119.00 (9) | C10—C9—H9 | 120.1 |
N2—C5—N1 | 118.85 (9) | C6—C7—C8 | 118.52 (10) |
N2—C5—C4 | 123.59 (10) | C6—C7—H7 | 120.7 |
N1—C5—C4 | 117.56 (10) | C8—C7—H7 | 120.7 |
C1—C2—C3 | 118.24 (10) | C9—C8—C7 | 120.61 (10) |
C1—C2—H2 | 120.9 | C9—C8—H8 | 119.7 |
C3—C2—H2 | 120.9 | C7—C8—H8 | 119.7 |
C4—C3—C2 | 120.80 (10) | N3—C6—C7 | 120.36 (10) |
C4—C3—H3 | 119.6 | N3—C6—H6 | 119.8 |
C2—C3—H3 | 119.6 | C7—C6—H6 | 119.8 |
C3—C4—C5 | 119.75 (10) | O1—N5—O3 | 120.47 (10) |
C3—C4—H4 | 120.1 | O1—N5—O2 | 120.79 (10) |
C5—C4—H4 | 120.1 | O3—N5—O2 | 118.75 (9) |
C1—N1—C5—N2 | 179.64 (10) | C6—N3—C10—N4 | −179.08 (11) |
C1—N1—C5—C4 | −0.41 (16) | C6—N3—C10—C9 | 1.19 (16) |
C1—C2—C3—C4 | 0.58 (17) | N4—C10—C9—C8 | 179.21 (12) |
C2—C3—C4—C5 | −1.08 (17) | N3—C10—C9—C8 | −1.08 (17) |
N2—C5—C4—C3 | −179.06 (11) | C10—C9—C8—C7 | 0.12 (18) |
N1—C5—C4—C3 | 0.98 (16) | C6—C7—C8—C9 | 0.78 (18) |
C5—N1—C1—C2 | −0.09 (17) | C10—N3—C6—C7 | −0.30 (17) |
C3—C2—C1—N1 | 0.01 (16) | C8—C7—C6—N3 | −0.71 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O2 | 0.866 (16) | 1.956 (16) | 2.7983 (13) | 164 (2) |
N4—H4B···O4 | 0.86 | 2.18 | 2.9564 (14) | 150 |
N4—H4A···O3 | 0.86 | 2.06 | 2.8959 (13) | 164 |
N1—H1A···O5 | 0.920 (16) | 1.878 (16) | 2.7790 (13) | 166 (2) |
N2—H2A···O4 | 0.86 | 2.04 | 2.8915 (14) | 170 |
N2—H2B···O3i | 0.86 | 2.10 | 2.8856 (13) | 152 |
N4—H4B···O6 | 0.86 | 2.45 | 3.2450 (14) | 154 |
Symmetry code: (i) x, −y+1, z+1/2. |
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