Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520619011272/px5015sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520619011272/px5015Isup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520619011272/px5015sup3.pdf |
CCDC reference: 1886394
Data collection: Bruker APEX2; cell refinement: Bruker SAINT; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS2013/1 (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).
C6H9N3O3 | F(000) = 360 |
Mr = 171.16 | Dx = 1.492 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8459 reflections |
a = 6.8785 (1) Å | θ = 2.8–51.4° |
b = 8.6396 (1) Å | µ = 0.12 mm−1 |
c = 12.8573 (2) Å | T = 90 K |
β = 94.351 (1)° | Block, colorless |
V = 761.88 (2) Å3 | 0.45 × 0.42 × 0.38 mm |
Z = 4 |
Bruker APEX-II CCD diffractometer | 8459 independent reflections |
Radiation source: fine-focus sealed tube | 7409 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω scans | θmax = 51.4°, θmin = 2.8° |
Absorption correction: analytical SADABS(BRUKER, 2006) | h = −15→15 |
Tmin = 0.705, Tmax = 0.750 | k = 0→18 |
8459 measured reflections | l = 0→28 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Primary atom site location: structure-invariant direct methods |
R[F2 > 2σ(F2)] = 0.032 | Secondary atom site location: difference Fourier map |
wR(F2) = 0.096 | Hydrogen site location: inferred from neighbouring sites |
S = 1.05 | H atoms treated by a mixture of independent and constrained refinement |
8459 reflections | w = 1/[σ2(Fo2) + (0.0528P)2 + 0.0396P] where P = (Fo2 + 2Fc2)/3 |
145 parameters | (Δ/σ)max = 0.002 |
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 > 2sigma(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 | ||
H2 | 0.6492 (12) | 1.0277 (10) | −0.1413 (6) | 0.0239 (18)* | |
H6B | 0.6859 (11) | 1.0814 (9) | 0.2521 (6) | 0.0191 (16)* | |
H5B | 0.9873 (11) | 0.9821 (9) | 0.1992 (6) | 0.0182 (15)* | |
H6A | 0.7972 (12) | 0.9788 (10) | 0.3440 (6) | 0.0232 (17)* | |
H5A | 0.9154 (12) | 0.8111 (10) | 0.2128 (6) | 0.0227 (17)* | |
H3 | 0.5741 (16) | 0.8141 (12) | 0.3256 (8) | 0.038 (2)* | |
H4C | 0.6413 (14) | 0.6220 (11) | 0.1413 (8) | 0.033 (2)* | |
H4B | 0.6552 (14) | 0.5590 (11) | 0.0279 (7) | 0.035 (2)* | |
H4A | 0.8431 (15) | 0.5977 (11) | 0.1042 (8) | 0.038 (2)* | |
N2 | 0.78921 (3) | 0.91339 (2) | 0.087093 (16) | 0.01057 (3) | |
O3 | 0.55999 (3) | 0.87979 (3) | 0.269883 (17) | 0.01618 (4) | |
N3 | 0.82263 (3) | 1.18946 (3) | 0.034447 (19) | 0.01301 (3) | |
N1 | 0.65237 (4) | 0.81923 (3) | −0.062631 (18) | 0.01320 (3) | |
C1 | 0.71659 (4) | 0.78600 (3) | 0.035743 (19) | 0.01188 (4) | |
C2 | 0.68468 (4) | 0.97335 (3) | −0.076302 (19) | 0.01226 (4) | |
C3 | 0.76877 (3) | 1.03302 (3) | 0.015313 (18) | 0.01066 (3) | |
C5 | 0.87269 (4) | 0.91562 (3) | 0.19572 (2) | 0.01350 (4) | |
C6 | 0.72842 (5) | 0.97458 (3) | 0.27091 (2) | 0.01492 (4) | |
O1 | 0.80240 (5) | 1.27862 (3) | −0.04044 (2) | 0.02093 (5) | |
O2 | 0.88617 (5) | 1.22880 (3) | 0.12263 (2) | 0.02124 (5) | |
C4 | 0.71365 (5) | 0.62878 (3) | 0.08221 (3) | 0.01834 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N2 | 0.01200 (7) | 0.01087 (6) | 0.00863 (6) | 0.00042 (5) | −0.00059 (5) | 0.00052 (5) |
O3 | 0.01664 (8) | 0.01973 (9) | 0.01196 (7) | −0.00067 (6) | −0.00027 (5) | 0.00469 (6) |
N3 | 0.01415 (7) | 0.01149 (7) | 0.01339 (7) | −0.00076 (5) | 0.00095 (5) | 0.00097 (5) |
N1 | 0.01482 (8) | 0.01402 (8) | 0.01060 (7) | 0.00067 (6) | −0.00022 (5) | −0.00254 (5) |
C1 | 0.01339 (8) | 0.01085 (7) | 0.01135 (8) | 0.00060 (6) | 0.00071 (6) | −0.00076 (5) |
C2 | 0.01310 (8) | 0.01471 (8) | 0.00884 (7) | 0.00169 (6) | −0.00006 (5) | 0.00002 (6) |
C3 | 0.01163 (7) | 0.01083 (7) | 0.00940 (7) | 0.00056 (5) | 0.00001 (5) | 0.00063 (5) |
C5 | 0.01423 (8) | 0.01604 (9) | 0.00979 (7) | 0.00065 (7) | −0.00201 (6) | 0.00122 (6) |
C6 | 0.01958 (10) | 0.01522 (9) | 0.00990 (8) | −0.00074 (7) | 0.00077 (7) | −0.00030 (6) |
O1 | 0.03094 (12) | 0.01369 (8) | 0.01810 (9) | −0.00003 (7) | 0.00144 (8) | 0.00577 (6) |
O2 | 0.02953 (12) | 0.01657 (9) | 0.01665 (9) | −0.00693 (8) | −0.00471 (8) | −0.00156 (7) |
C4 | 0.02396 (12) | 0.01131 (9) | 0.01971 (11) | −0.00028 (8) | 0.00142 (9) | 0.00133 (7) |
N2—C1 | 1.3589 (3) | C2—C3 | 1.3728 (3) |
N2—C3 | 1.3857 (3) | C2—H2 | 0.974 (8) |
N2—C5 | 1.4694 (3) | C5—C6 | 1.5246 (4) |
O3—C6 | 1.4180 (4) | C5—H5B | 0.974 (8) |
O3—H3 | 0.913 (10) | C5—H5A | 0.970 (8) |
N3—O2 | 1.2316 (3) | C6—H6B | 0.992 (8) |
N3—O1 | 1.2327 (3) | C6—H6A | 1.020 (8) |
N3—C3 | 1.4180 (3) | C4—H4C | 0.941 (9) |
N1—C1 | 1.3389 (3) | C4—H4B | 0.985 (10) |
N1—C2 | 1.3635 (4) | C4—H4A | 0.952 (11) |
C1—C4 | 1.4846 (4) | ||
C1—N2—C3 | 105.40 (2) | N2—C5—H5B | 107.9 (5) |
C1—N2—C5 | 125.11 (2) | C6—C5—H5B | 109.7 (4) |
C3—N2—C5 | 129.49 (2) | N2—C5—H5A | 107.1 (5) |
C6—O3—H3 | 108.3 (7) | C6—C5—H5A | 111.6 (5) |
O2—N3—O1 | 123.90 (3) | H5B—C5—H5A | 108.0 (7) |
O2—N3—C3 | 119.51 (2) | O3—C6—C5 | 111.82 (2) |
O1—N3—C3 | 116.59 (2) | O3—C6—H6B | 108.0 (4) |
C1—N1—C2 | 106.61 (2) | C5—C6—H6B | 110.5 (4) |
N1—C1—N2 | 111.60 (2) | O3—C6—H6A | 110.5 (5) |
N1—C1—C4 | 124.24 (2) | C5—C6—H6A | 108.5 (4) |
N2—C1—C4 | 124.14 (2) | H6B—C6—H6A | 107.4 (7) |
N1—C2—C3 | 108.56 (2) | C1—C4—H4C | 114.0 (6) |
N1—C2—H2 | 123.3 (5) | C1—C4—H4B | 107.0 (6) |
C3—C2—H2 | 128.1 (5) | H4C—C4—H4B | 108.7 (8) |
C2—C3—N2 | 107.83 (2) | C1—C4—H4A | 109.7 (6) |
C2—C3—N3 | 126.47 (2) | H4C—C4—H4A | 106.4 (8) |
N2—C3—N3 | 125.69 (2) | H4B—C4—H4A | 111.1 (8) |
N2—C5—C6 | 112.39 (2) | ||
C2—N1—C1—N2 | 0.24 (3) | C5—N2—C3—C2 | 179.19 (2) |
C2—N1—C1—C4 | −178.28 (3) | C1—N2—C3—N3 | 179.08 (2) |
C3—N2—C1—N1 | −0.18 (3) | C5—N2—C3—N3 | −1.78 (4) |
C5—N2—C1—N1 | −179.37 (2) | O2—N3—C3—C2 | 175.59 (3) |
C3—N2—C1—C4 | 178.34 (3) | O1—N3—C3—C2 | −4.59 (4) |
C5—N2—C1—C4 | −0.85 (4) | O2—N3—C3—N2 | −3.26 (4) |
C1—N1—C2—C3 | −0.20 (3) | O1—N3—C3—N2 | 176.56 (3) |
N1—C2—C3—N2 | 0.09 (3) | C1—N2—C5—C6 | −99.64 (3) |
N1—C2—C3—N3 | −178.93 (2) | C3—N2—C5—C6 | 81.37 (3) |
C1—N2—C3—C2 | 0.05 (3) | N2—C5—C6—O3 | 60.85 (3) |