Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520616010581/gw5044sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520616010581/gw5044Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2052520616010581/gw5044Isup3.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520616010581/gw5044sup4.pdf |
CCDC reference: 1451587
Data collection: 'CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01)' _computing_cell_refinement 'CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01)'; data reduction: 'CrysAlis PRO, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01)'; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: XD2006 (Volkov et al., 2006); molecular graphics: XD2006 (Volkov et al., 2006); software used to prepare material for publication: XD2006 (Volkov et al., 2006).
C3H3N3O2 | F(000) = 232 |
Mr = 113.08 | Dx = 1.718 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 1 21/c 1 | Cell parameters from 15907 reflections |
a = 7.3215 (1) Å | θ = 3.7–53.1° |
b = 9.8106 (1) Å | µ = 0.15 mm−1 |
c = 6.7539 (1) Å | T = 110 K |
β = 115.710 (2)° | Block, colorless |
V = 437.10 (1) Å3 | 0.82 × 0.25 × 0.25 mm |
Z = 4 |
Xcalibur, Eos, Nova diffractometer | 5222 independent reflections |
Radiation source: fine-focus sealed tube | 4384 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ω scans | θmax = 53.3°, θmin = 3.1° |
Absorption correction: analytical 'CrysAlisPro, Agilent Technologies,' Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.' | h = −16→16 |
Tmin = 0.918, Tmax = 0.971 | k = −22→22 |
36394 measured reflections | l = −14→15 |
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)] = 0.023 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.046 | H-atom parameters not defined? |
S = 1.64 | w2 = 1/[s2(Fo2)] |
4224 reflections | (Δ/σ)max = 0.00003 |
198 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Experimental. A nitrogen gas-flow low temperature device was used. A face indexed analytical absorption correction was performed. |
Refinement. Reflections were merged with Sortav (Blessing, 1995). |
x | y | z | Uiso*/Ueq | ||
O(1) | −0.31880 (3) | 0.46075 (2) | 0.22196 (5) | 0.015 | |
O(2) | −0.31676 (4) | 0.68270 (2) | 0.21843 (6) | 0.019 | |
N(1) | 0.06896 (3) | 0.457167 (18) | 0.26253 (3) | 0.010 | |
N(3) | −0.23753 (3) | 0.570910 (19) | 0.22799 (3) | 0.011 | |
N(2) | 0.06721 (3) | 0.684992 (18) | 0.25488 (3) | 0.011 | |
C(2) | −0.03474 (3) | 0.569642 (19) | 0.24893 (3) | 0.010 | |
C(1) | 0.25118 (3) | 0.502892 (18) | 0.27753 (3) | 0.012 | |
C(3) | 0.25216 (3) | 0.643865 (19) | 0.27306 (4) | 0.012 | |
H(2) | 0.019484 | 0.777555 | 0.247604 | 0.0133 (13) | |
H(1) | 0.375277 | 0.438774 | 0.290745 | 0.0249 (14) | |
H(3) | 0.374494 | 0.708367 | 0.282196 | 0.0266 (15) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O(1) | 0.01196 (7) | 0.01240 (7) | 0.02235 (9) | −0.00248 (6) | 0.00914 (7) | 0.00013 (6) |
O(2) | 0.01392 (9) | 0.01207 (8) | 0.03570 (13) | 0.00278 (6) | 0.01409 (9) | 0.00100 (8) |
N(1) | 0.00934 (6) | 0.00793 (5) | 0.01393 (6) | 0.00021 (4) | 0.00551 (5) | 0.00007 (4) |
N(3) | 0.00923 (5) | 0.00981 (5) | 0.01595 (6) | 0.00006 (5) | 0.00657 (5) | 0.00034 (5) |
N(2) | 0.00991 (6) | 0.00792 (5) | 0.01527 (7) | −0.00017 (4) | 0.00636 (5) | 0.00002 (4) |
C(2) | 0.00852 (5) | 0.00813 (5) | 0.01287 (6) | 0.00007 (5) | 0.00530 (5) | 0.00015 (4) |
C(1) | 0.00918 (5) | 0.00986 (5) | 0.01624 (7) | 0.00074 (5) | 0.00612 (5) | 0.00002 (5) |
C(3) | 0.00973 (6) | 0.00988 (5) | 0.01769 (7) | −0.00094 (5) | 0.00688 (5) | 0.00007 (5) |
O(1)—N(3) | 1.2259 (3) | N(2)—C(3) | 1.3665 (3) |
O(2)—N(3) | 1.2292 (3) | N(2)—H(2) | 0.9666 (2) |
N(1)—C(2) | 1.3198 (3) | C(1)—C(3) | 1.3834 (2) |
N(1)—C(1) | 1.3690 (3) | C(1)—H(1) | 1.0765 (2) |
N(3)—C(2) | 1.4291 (3) | C(3)—H(3) | 1.0763 (2) |
N(2)—C(2) | 1.3466 (3) | ||
C(2)—N(1)—C(1) | 104.115 (16) | N(1)—C(2)—N(2) | 113.947 (18) |
O(1)—N(3)—O(2) | 125.00 (2) | N(3)—C(2)—N(2) | 122.292 (17) |
O(1)—N(3)—C(2) | 117.652 (19) | N(1)—C(1)—C(3) | 109.883 (17) |
O(2)—N(3)—C(2) | 117.34 (2) | N(1)—C(1)—H(1) | 125.104 (17) |
C(2)—N(2)—C(3) | 105.627 (16) | C(3)—C(1)—H(1) | 125.013 (18) |
C(2)—N(2)—H(2) | 127.20 (2) | N(2)—C(3)—C(1) | 106.427 (16) |
C(3)—N(2)—H(2) | 127.175 (19) | N(2)—C(3)—H(3) | 126.805 (17) |
N(1)—C(2)—N(3) | 123.760 (18) | C(1)—C(3)—H(3) | 126.768 (18) |
C(1)—N(1)—C(2)—N(3) | 179.29 (3) | C(2)—N(2)—C(3)—C(1) | −0.107 (17) |
C(1)—N(1)—C(2)—N(2) | −0.245 (17) | C(2)—N(2)—C(3)—H(3) | 179.92 (3) |
C(2)—N(1)—C(1)—C(3) | 0.165 (17) | H(2)—N(2)—C(2)—N(1) | −179.85 (3) |
C(2)—N(1)—C(1)—H(1) | −179.80 (3) | H(2)—N(2)—C(2)—N(3) | 0.612 (19) |
O(1)—N(3)—C(2)—N(1) | −0.17 (2) | H(2)—N(2)—C(3)—C(1) | 179.97 (3) |
O(1)—N(3)—C(2)—N(2) | 179.33 (3) | H(2)—N(2)—C(3)—H(3) | −0.004 (19) |
O(2)—N(3)—C(2)—N(1) | 179.50 (3) | N(1)—C(1)—C(3)—N(2) | −0.036 (17) |
O(2)—N(3)—C(2)—N(2) | −1.00 (2) | N(1)—C(1)—C(3)—H(3) | 179.93 (3) |
C(3)—N(2)—C(2)—N(1) | 0.228 (17) | H(1)—C(1)—C(3)—N(2) | 179.93 (3) |
C(3)—N(2)—C(2)—N(3) | −179.31 (3) | H(1)—C(1)—C(3)—H(3) | −0.100 (18) |