Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S205252062100740X/um5050sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HMTN00sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HMTN01sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HMTN02sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HOTN00sup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HOTN01sup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HOTN02sup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HMTX18sup8.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HMTX19sup9.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HMTX20sup10.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HOTX21sup11.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HOTX22sup12.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205252062100740X/um5050HOTX23sup13.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S205252062100740X/um5050sup14.pdf | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205252062100740X/um5050sup15.cml |
CCDC references: 2097452; 2097453; 2097454; 2097455; 2097456; 2097457; 2097458; 2097459; 2097460; 2097461; 2097462; 2097463
Data collection: MAATEL/ANSTO control program for HMTN00, HMTN01, HMTN02, HOTN00, HOTN01, HOTN02. Cell refinement: LaueG (Piltz, 2011) for HMTN00, HMTN01, HMTN02, HOTN00, HOTN01, HOTN02; SAINT V8.38A (?, 2016) for HMTX18, HMTX19, HMTX20, HOTX21, HOTX22, HOTX23. Data reduction: argonne_boxes (Wilkinson et al., 1988) & LaueG (Piltz, 2011) for HMTN00, HMTN01, HMTN02, HOTN00, HOTN01, HOTN02; SAINT V8.38A (?, 2016) for HMTX18, HMTX19, HMTX20, HOTX21, HOTX22, HOTX23. Program(s) used to solve structure: from X-ray model at 5 K for HMTN00, HOTN00; from X-ray model at 105 K for HMTN01, HOTN01; from X-ray model at 295 K for HMTN02, HOTN02; ShelXT (Sheldrick, 2015) for HMTX18, HMTX19, HMTX20, HOTX21, HOTX22, HOTX23. Program(s) used to refine structure: XL (Sheldrick, 2008) for HMTN00, HMTN01, HMTN02, HOTN00, HOTN01, HOTN02; SHELXL (Sheldrick, 2015) for HMTX18, HMTX19, HMTX20, HOTX21, HOTX22, HOTX23. Molecular graphics: Olex2 1.3 (Dolomanov et al., 2009) for HMTN00, HMTN01, HMTN02, HOTN00, HOTN01, HOTN02; Olex2 (Dolomanov et al., 2009) for HMTX18, HMTX19, HMTX20, HOTX21, HOTX22, HOTX23. Software used to prepare material for publication: Olex2 1.3 (Dolomanov et al., 2009) for HMTN00, HMTN01, HMTN02, HOTN00, HOTN01, HOTN02; Olex2 (Dolomanov et al., 2009) for HMTX18, HMTX19, HMTX20, HOTX21, HOTX22, HOTX23.
C6H9N3O2 | F(000) = 92 |
Mr = 155.16 | Dx = 1.464 Mg m−3 |
Monoclinic, P21 | Neutron radiation, λ = 0.80 Å |
a = 5.1651 (2) Å | Cell parameters from 4301 reflections |
b = 7.2324 (2) Å | θ = 3.6–30.5° |
c = 9.4957 (3) Å | µ = 0.0 mm−1 |
β = 97.065 (2)° | T = 5 K |
V = 352.03 (2) Å3 | Plate, colourless |
Z = 2 | 0.45 × 0.35 × 0.30 mm |
KOALA diffractometer | Rint = 0.138 |
Radiation source: nuclear reactor, OPAL reactor, ANSTO, Lucas Heights, Australia | θmax = 71.1° |
Laue scans | h = −9→9 |
16604 measured reflections | k = −13→13 |
1629 independent reflections | l = −15→15 |
1267 reflections with I > 2σ(I) |
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.060 | w = 1/[σ2(Fo2) + (0.030P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.082 | (Δ/σ)max < 0.001 |
S = 1.21 | Δρmax = 1.62 e Å−3 |
1629 reflections | Δρmin = −1.99 e Å−3 |
181 parameters | Absolute structure: Absolute structure known from synthesis |
1 restraint |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O2 | 0.3153 (3) | 0.4532 (3) | 1.0159 (2) | 0.0075 (4) | |
O1 | 0.7418 (3) | 0.4476 (3) | 1.0990 (3) | 0.0089 (4) | |
N1 | 0.8766 (2) | 0.63531 (16) | 0.87289 (15) | 0.0071 (3) | |
H1A | 0.9462 (7) | 0.6394 (6) | 0.7740 (5) | 0.0197 (8) | |
H1B | 1.0169 (7) | 0.5658 (5) | 0.9425 (5) | 0.0218 (9) | |
H1C | 0.8500 (8) | 0.7702 (5) | 0.9113 (5) | 0.0201 (8) | |
N3 | 0.7208 (2) | 0.44435 (18) | 0.38771 (17) | 0.0079 (3) | |
H3 | 0.6899 (7) | 0.4374 (6) | 0.2770 (5) | 0.0203 (8) | |
N2 | 0.9220 (2) | 0.51526 (17) | 0.60102 (15) | 0.0074 (3) | |
C1 | 0.5534 (3) | 0.4757 (2) | 1.0048 (2) | 0.0052 (3) | |
C4 | 0.6990 (3) | 0.4138 (2) | 0.6167 (2) | 0.0069 (4) | |
C6 | 0.5721 (3) | 0.3694 (2) | 0.4843 (2) | 0.0069 (3) | |
H6 | 0.3963 (8) | 0.2908 (6) | 0.4535 (6) | 0.0232 (9) | |
C2 | 0.6204 (3) | 0.5360 (2) | 0.8578 (2) | 0.0056 (3) | |
H2 | 0.4702 (6) | 0.6330 (6) | 0.8096 (5) | 0.0189 (8) | |
C5 | 0.9266 (3) | 0.5300 (3) | 0.4619 (2) | 0.0076 (3) | |
H5 | 1.0729 (8) | 0.6031 (6) | 0.4118 (6) | 0.0244 (10) | |
C3 | 0.6302 (3) | 0.3659 (2) | 0.7616 (2) | 0.0066 (3) | |
H3A | 0.7723 (8) | 0.2667 (6) | 0.8134 (5) | 0.0214 (9) | |
H3B | 0.4375 (8) | 0.2981 (6) | 0.7524 (6) | 0.0248 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0047 (6) | 0.0086 (8) | 0.0093 (13) | 0.0003 (6) | 0.0014 (6) | 0.0016 (7) |
O1 | 0.0054 (6) | 0.0104 (8) | 0.0104 (12) | 0.0007 (6) | −0.0010 (6) | 0.0013 (8) |
N1 | 0.0066 (4) | 0.0055 (5) | 0.0093 (8) | −0.0006 (3) | 0.0011 (4) | −0.0005 (4) |
H1A | 0.0160 (13) | 0.0258 (19) | 0.018 (3) | −0.0037 (13) | 0.0057 (14) | −0.0005 (17) |
H1B | 0.0184 (14) | 0.0194 (19) | 0.026 (3) | 0.0011 (12) | −0.0021 (15) | 0.0066 (16) |
H1C | 0.0250 (16) | 0.0116 (16) | 0.023 (3) | −0.0007 (12) | 0.0018 (16) | −0.0034 (14) |
N3 | 0.0074 (4) | 0.0089 (5) | 0.0074 (9) | −0.0005 (4) | 0.0004 (4) | 0.0003 (4) |
H3 | 0.0240 (15) | 0.026 (2) | 0.010 (3) | −0.0033 (15) | −0.0010 (14) | −0.0005 (15) |
N2 | 0.0059 (4) | 0.0085 (5) | 0.0078 (8) | −0.0015 (4) | 0.0002 (4) | −0.0007 (5) |
C1 | 0.0060 (5) | 0.0053 (7) | 0.0046 (11) | 0.0002 (5) | 0.0015 (5) | 0.0002 (5) |
C4 | 0.0055 (5) | 0.0069 (7) | 0.0080 (11) | −0.0010 (5) | −0.0003 (5) | 0.0001 (6) |
C6 | 0.0067 (5) | 0.0079 (7) | 0.0061 (11) | −0.0017 (5) | 0.0009 (6) | −0.0007 (6) |
H6 | 0.0176 (15) | 0.031 (2) | 0.020 (3) | −0.0109 (14) | −0.0014 (15) | −0.0011 (17) |
C2 | 0.0053 (5) | 0.0054 (7) | 0.0060 (10) | 0.0002 (5) | 0.0002 (5) | 0.0012 (6) |
H2 | 0.0144 (12) | 0.0192 (17) | 0.022 (3) | 0.0052 (12) | −0.0012 (14) | 0.0029 (15) |
C5 | 0.0070 (5) | 0.0084 (7) | 0.0079 (11) | −0.0015 (5) | 0.0025 (6) | −0.0002 (6) |
H5 | 0.0215 (15) | 0.028 (2) | 0.026 (3) | −0.0107 (14) | 0.0098 (16) | 0.0017 (17) |
C3 | 0.0086 (5) | 0.0060 (7) | 0.0053 (10) | −0.0023 (5) | 0.0016 (6) | −0.0005 (6) |
H3A | 0.0301 (18) | 0.0166 (18) | 0.017 (3) | 0.0072 (14) | 0.0012 (16) | −0.0004 (14) |
H3B | 0.0210 (16) | 0.025 (2) | 0.029 (3) | −0.0139 (14) | 0.0057 (17) | −0.0048 (17) |
O2—C1 | 1.258 (2) | N2—C5 | 1.329 (2) |
O1—C1 | 1.255 (3) | C1—C2 | 1.542 (3) |
N1—H1A | 1.046 (5) | C4—C6 | 1.382 (3) |
N1—H1B | 1.047 (4) | C4—C3 | 1.503 (3) |
N1—H1C | 1.056 (4) | C2—H2 | 1.103 (4) |
N1—C2 | 1.4970 (19) | C2—C3 | 1.537 (2) |
N3—H3 | 1.045 (5) | C6—H6 | 1.081 (5) |
N3—C6 | 1.378 (2) | C3—H3A | 1.098 (5) |
N3—C5 | 1.351 (2) | C3—H3B | 1.103 (4) |
N2—C4 | 1.3891 (19) | C5—H5 | 1.080 (5) |
C4—N2—C5 | 105.40 (14) | C3—C2—H2 | 109.6 (3) |
O1—C1—C2 | 116.78 (16) | C4—C3—H3A | 109.9 (3) |
N1—C2—C3 | 110.34 (13) | N2—C5—H5 | 125.2 (3) |
N2—C4—C3 | 120.82 (15) | C4—C6—H6 | 131.1 (3) |
N2—C5—N3 | 111.87 (15) | O1—C1—O2 | 126.9 (2) |
C2—N1—H1A | 109.0 (3) | N1—C2—C1 | 110.08 (14) |
C5—N3—H3 | 124.0 (2) | C2—C3—C4 | 112.85 (13) |
C1—C2—H2 | 109.3 (3) | C3—C4—C6 | 129.79 (14) |
C2—C3—H3B | 107.9 (3) | C2—N1—H1C | 109.0 (2) |
N3—C6—H6 | 123.1 (3) | N1—C2—H2 | 107.6 (2) |
C5—N3—C6 | 107.49 (15) | C2—C3—H3A | 109.0 (3) |
O2—C1—C2 | 116.30 (16) | C4—C3—H3B | 110.0 (3) |
C1—C2—C3 | 109.83 (12) | N3—C5—H5 | 122.9 (3) |
N2—C4—C6 | 109.39 (15) | H1B—N1—H1C | 109.6 (3) |
N3—C6—C4 | 105.86 (14) | H1A—N1—H1C | 110.9 (4) |
C2—N1—H1B | 111.4 (2) | H1A—N1—H1B | 107.0 (3) |
C6—N3—H3 | 128.5 (2) | H3A—C3—H3B | 107.0 (3) |
C5—N2—C4—C3 | 178.96 (15) | O1—C1—C2—N1 | −27.5 (2) |
C6—N3—C5—N2 | 0.2 (2) | O2—C1—C2—C3 | −83.19 (19) |
O1—C1—C2—C3 | 94.23 (19) | C2—C3—C4—N2 | 53.59 (19) |
N1—C2—C3—C4 | −57.55 (18) | C3—C4—C6—N3 | −178.75 (14) |
C2—C3—C4—C6 | −127.54 (17) | H1A—N1—C2—H2 | −78.0 (4) |
H1A—N1—C2—C1 | 162.9 (3) | H1B—N1—C2—H2 | 164.2 (4) |
H1B—N1—C2—C1 | 45.1 (3) | H1C—N1—C2—H2 | 43.2 (4) |
H1C—N1—C2—C1 | −75.9 (3) | H3—N3—C5—N2 | −178.7 (3) |
C4—N2—C5—H5 | 178.8 (3) | H3—N3—C6—C4 | 178.6 (3) |
H3—N3—C5—H5 | 2.4 (5) | O2—C1—C2—H2 | 37.1 (3) |
H3—N3—C6—H6 | −0.2 (5) | N1—C2—C3—H3A | 64.9 (3) |
C5—N2—C4—C6 | −0.12 (17) | C1—C2—C3—H3B | 59.2 (3) |
C5—N3—C6—C4 | −0.23 (17) | H2—C2—C3—H3B | −61.0 (4) |
O2—C1—C2—N1 | 155.13 (16) | H3B—C3—C4—N2 | 174.2 (3) |
C1—C2—C3—C4 | −179.07 (13) | C3—C4—C6—H6 | −0.1 (4) |
N2—C4—C6—N3 | 0.22 (16) | N1—C2—C3—H3B | −179.3 (3) |
H1A—N1—C2—C3 | 41.5 (3) | H2—C2—C3—C4 | 60.8 (3) |
H1B—N1—C2—C3 | −76.3 (3) | H3A—C3—C4—N2 | −68.3 (3) |
H1C—N1—C2—C3 | 162.7 (3) | H3B—C3—C4—C6 | −7.0 (3) |
C6—N3—C5—H5 | −178.7 (3) | C1—C2—C3—H3A | −56.7 (3) |
C5—N3—C6—H6 | −179.0 (3) | H2—C2—C3—H3A | −176.8 (3) |
O1—C1—C2—H2 | −145.5 (3) | H3A—C3—C4—C6 | 110.6 (3) |
C4—N2—C5—N3 | 0.0 (2) | N2—C4—C6—H6 | 178.8 (3) |
C6H9N3O2 | F(000) = 92 |
Mr = 155.16 | Dx = 1.455 Mg m−3 |
Monoclinic, P21 | Neutron radiation, λ = 0.80 Å |
a = 5.1656 (2) Å | Cell parameters from 2706 reflections |
b = 7.2761 (3) Å | θ = 3.5–30.4° |
c = 9.4978 (3) Å | µ = 0.0 mm−1 |
β = 97.316 (3)° | T = 105 K |
V = 354.07 (2) Å3 | Plate, colourless |
Z = 2 | 0.45 × 0.35 × 0.30 mm |
KOALA diffractometer | Rint = 0.149 |
Radiation source: nuclear reactor, OPAL reactor, ANSTO, Lucas Heights, Australia | θmax = 70.9° |
Laue scans | h = −8→8 |
12588 measured reflections | k = −12→12 |
1359 independent reflections | l = −14→14 |
939 reflections with I > 2σ(I) |
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.050 | w = 1/[σ2(Fo2) + (0.030P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.071 | (Δ/σ)max < 0.001 |
S = 1.00 | Δρmax = 1.12 e Å−3 |
1292 reflections | Δρmin = −1.18 e Å−3 |
181 parameters | Absolute structure: Absolute structure known from synthesis |
1 restraint |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O2 | 0.3144 (4) | 0.4517 (4) | 1.0143 (3) | 0.0139 (5) | |
O1 | 0.7401 (4) | 0.4458 (4) | 1.0988 (3) | 0.0147 (5) | |
N1 | 0.8736 (2) | 0.63497 (19) | 0.87368 (17) | 0.0098 (3) | |
H1A | 0.9437 (8) | 0.6399 (7) | 0.7747 (5) | 0.0230 (9) | |
H1B | 1.0151 (8) | 0.5663 (6) | 0.9429 (6) | 0.0251 (10) | |
H1C | 0.8476 (8) | 0.7676 (6) | 0.9129 (5) | 0.0235 (10) | |
N3 | 0.7209 (2) | 0.4445 (2) | 0.38776 (19) | 0.0131 (3) | |
H3 | 0.6915 (8) | 0.4363 (7) | 0.2760 (6) | 0.0245 (10) | |
N2 | 0.9212 (2) | 0.5163 (2) | 0.60161 (18) | 0.0132 (3) | |
C1 | 0.5529 (3) | 0.4744 (2) | 1.0041 (2) | 0.0088 (4) | |
C4 | 0.6986 (3) | 0.4149 (3) | 0.6164 (2) | 0.0108 (4) | |
C6 | 0.5727 (3) | 0.3695 (3) | 0.4839 (2) | 0.0125 (4) | |
H6 | 0.3972 (9) | 0.2917 (7) | 0.4537 (6) | 0.0306 (11) | |
C2 | 0.6190 (3) | 0.5354 (3) | 0.8574 (2) | 0.0089 (4) | |
H2 | 0.4688 (7) | 0.6316 (7) | 0.8087 (5) | 0.0225 (9) | |
C5 | 0.9261 (3) | 0.5314 (3) | 0.4625 (2) | 0.0128 (4) | |
H5 | 1.0719 (9) | 0.6041 (7) | 0.4124 (6) | 0.0327 (12) | |
C3 | 0.6304 (4) | 0.3662 (3) | 0.7604 (2) | 0.0116 (4) | |
H3A | 0.7735 (10) | 0.2668 (7) | 0.8138 (6) | 0.0288 (11) | |
H3B | 0.4390 (10) | 0.2999 (7) | 0.7520 (6) | 0.0309 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0100 (7) | 0.0187 (12) | 0.0132 (16) | −0.0002 (9) | 0.0022 (8) | 0.0025 (10) |
O1 | 0.0139 (8) | 0.0213 (11) | 0.0092 (14) | −0.0004 (9) | 0.0025 (8) | 0.0036 (10) |
N1 | 0.0111 (5) | 0.0108 (7) | 0.0074 (10) | −0.0014 (4) | 0.0012 (5) | 0.0003 (5) |
H1A | 0.0250 (16) | 0.033 (2) | 0.012 (3) | −0.0058 (17) | 0.0078 (17) | −0.001 (2) |
H1B | 0.0232 (17) | 0.026 (2) | 0.024 (3) | −0.0007 (15) | −0.0052 (18) | 0.0060 (18) |
H1C | 0.0269 (18) | 0.018 (2) | 0.025 (3) | −0.0013 (15) | 0.0016 (18) | −0.0078 (17) |
N3 | 0.0169 (5) | 0.0152 (7) | 0.0075 (11) | 0.0006 (5) | 0.0030 (6) | 0.0013 (5) |
H3 | 0.0302 (17) | 0.032 (2) | 0.011 (3) | −0.0014 (19) | 0.0007 (17) | −0.0032 (19) |
N2 | 0.0134 (5) | 0.0165 (7) | 0.0097 (10) | −0.0030 (5) | 0.0016 (5) | −0.0004 (6) |
C1 | 0.0093 (6) | 0.0101 (9) | 0.0072 (13) | 0.0012 (6) | 0.0022 (7) | 0.0015 (6) |
C4 | 0.0125 (7) | 0.0113 (10) | 0.0091 (14) | −0.0005 (6) | 0.0025 (7) | 0.0004 (7) |
C6 | 0.0132 (7) | 0.0130 (9) | 0.0113 (14) | −0.0017 (7) | 0.0009 (7) | −0.0024 (8) |
H6 | 0.0273 (19) | 0.039 (3) | 0.024 (3) | −0.0147 (18) | −0.0010 (19) | −0.006 (2) |
C2 | 0.0102 (6) | 0.0098 (8) | 0.0067 (11) | −0.0001 (6) | 0.0005 (6) | 0.0017 (7) |
H2 | 0.0233 (15) | 0.024 (2) | 0.020 (3) | 0.0064 (16) | 0.0005 (17) | 0.0056 (18) |
C5 | 0.0154 (7) | 0.0150 (9) | 0.0083 (13) | −0.0011 (7) | 0.0032 (8) | 0.0021 (8) |
H5 | 0.033 (2) | 0.045 (3) | 0.021 (3) | −0.013 (2) | 0.009 (2) | 0.004 (2) |
C3 | 0.0169 (7) | 0.0101 (9) | 0.0082 (13) | −0.0026 (7) | 0.0026 (8) | −0.0010 (8) |
H3A | 0.045 (2) | 0.019 (2) | 0.023 (3) | 0.0102 (18) | 0.008 (2) | 0.0049 (18) |
H3B | 0.035 (2) | 0.036 (3) | 0.024 (3) | −0.0228 (19) | 0.011 (2) | −0.008 (2) |
O1—C1 | 1.251 (3) | C1—C2 | 1.542 (3) |
N2—C5 | 1.329 (3) | N1—H1A | 1.050 (5) |
C2—C3 | 1.543 (3) | C2—H2 | 1.102 (5) |
O2—C1 | 1.259 (3) | C6—H6 | 1.076 (5) |
N3—C5 | 1.355 (2) | N1—H1B | 1.046 (5) |
C3—C4 | 1.498 (3) | C3—H3A | 1.110 (6) |
N1—C2 | 1.492 (2) | N1—H1C | 1.049 (5) |
N3—C6 | 1.377 (2) | C3—H3B | 1.094 (6) |
C4—C6 | 1.381 (3) | N3—H3 | 1.055 (6) |
N2—C4 | 1.388 (2) | C5—H5 | 1.079 (5) |
C4—N2—C5 | 105.39 (15) | C3—C2—H2 | 109.5 (3) |
O1—C1—C2 | 117.24 (17) | C4—C3—H3A | 110.6 (3) |
N1—C2—C3 | 110.43 (14) | N2—C5—H5 | 125.6 (3) |
N2—C4—C3 | 120.82 (17) | C4—C6—H6 | 130.7 (3) |
N2—C5—N3 | 111.69 (15) | O1—C1—O2 | 126.7 (2) |
C2—N1—H1A | 108.9 (3) | N1—C2—C1 | 109.87 (14) |
C5—N3—H3 | 123.8 (3) | C2—C3—C4 | 112.81 (17) |
C1—C2—H2 | 109.7 (3) | C3—C4—C6 | 129.59 (17) |
C2—C3—H3B | 107.0 (3) | C2—N1—H1C | 109.4 (3) |
N3—C6—H6 | 123.5 (3) | N1—C2—H2 | 107.4 (3) |
C5—N3—C6 | 107.55 (16) | C2—C3—H3A | 108.7 (3) |
O2—C1—C2 | 116.04 (19) | C4—C3—H3B | 110.7 (3) |
C1—C2—C3 | 109.85 (16) | N3—C5—H5 | 122.8 (3) |
N2—C4—C6 | 109.57 (16) | H1A—N1—H1B | 106.6 (4) |
N3—C6—C4 | 105.81 (15) | H3A—C3—H3B | 106.8 (4) |
C2—N1—H1B | 111.7 (3) | H1A—N1—H1C | 111.1 (4) |
C6—N3—H3 | 128.6 (3) | H1B—N1—H1C | 109.1 (4) |
C5—N2—C4—C3 | 178.71 (18) | O1—C1—C2—N1 | −27.8 (3) |
C6—N3—C5—N2 | 0.4 (2) | O2—C1—C2—C3 | −83.5 (2) |
O1—C1—C2—C3 | 93.9 (2) | C2—C3—C4—N2 | 53.8 (2) |
N1—C2—C3—C4 | −57.6 (2) | C3—C4—C6—N3 | −178.28 (19) |
C2—C3—C4—C6 | −128.1 (2) | H1A—N1—C2—H2 | −77.9 (4) |
H1A—N1—C2—C1 | 162.9 (3) | H1B—N1—C2—H2 | 164.7 (4) |
H1B—N1—C2—C1 | 45.4 (4) | H1C—N1—C2—H2 | 43.8 (4) |
H1C—N1—C2—C1 | −75.5 (3) | H3—N3—C5—N2 | −178.0 (3) |
C4—N2—C5—H5 | 179.0 (4) | H3—N3—C6—C4 | 178.1 (4) |
H3—N3—C5—H5 | 2.6 (5) | O2—C1—C2—H2 | 37.0 (4) |
H3—N3—C6—H6 | −1.4 (6) | N1—C2—C3—H3A | 65.4 (4) |
C5—N2—C4—C6 | 0.3 (2) | C1—C2—C3—H3B | 59.1 (4) |
C5—N3—C6—C4 | −0.2 (2) | H2—C2—C3—H3B | −61.5 (4) |
O2—C1—C2—N1 | 154.83 (19) | H3B—C3—C4—N2 | 173.7 (3) |
C1—C2—C3—C4 | −178.98 (14) | C3—C4—C6—H6 | 1.2 (5) |
N2—C4—C6—N3 | −0.1 (2) | N1—C2—C3—H3B | −179.6 (3) |
H1A—N1—C2—C3 | 41.5 (3) | H2—C2—C3—C4 | 60.5 (3) |
H1B—N1—C2—C3 | −75.9 (4) | H3A—C3—C4—N2 | −68.1 (4) |
H1C—N1—C2—C3 | 163.2 (3) | H3B—C3—C4—C6 | −8.2 (4) |
C6—N3—C5—H5 | −179.0 (4) | C1—C2—C3—H3A | −56.0 (3) |
C5—N3—C6—H6 | −179.7 (4) | H2—C2—C3—H3A | −176.5 (4) |
O1—C1—C2—H2 | −145.7 (3) | H3A—C3—C4—C6 | 109.9 (4) |
C4—N2—C5—N3 | −0.5 (2) | N2—C4—C6—H6 | 179.4 (4) |
C6H9N3O2 | F(000) = 92 |
Mr = 155.16 | Dx = 1.428 Mg m−3 |
Monoclinic, P21 | Neutron radiation, λ = 0.80 Å |
a = 5.1854 (8) Å | Cell parameters from 2412 reflections |
b = 7.3998 (10) Å | θ = 3.5–30.2° |
c = 9.4976 (12) Å | µ = 0.0 mm−1 |
β = 98.182 (10)° | T = 295 K |
V = 360.72 (9) Å3 | Plate, colourless |
Z = 2 | 0.45 × 0.35 × 0.30 mm |
KOALA diffractometer | Rint = 0.134 |
Radiation source: nuclear reactor, OPAL reactor, ANSTO, Lucas Heights, Australia | θmax = 71.1° |
Laue scans | h = −8→8 |
20381 measured reflections | k = −12→12 |
1354 independent reflections | l = −14→14 |
914 reflections with I > 2σ(I) |
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.053 | w = 1/[σ2(Fo2) + (0.030P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.075 | (Δ/σ)max < 0.001 |
S = 1.11 | Δρmax = 0.77 e Å−3 |
1354 reflections | Δρmin = −1.00 e Å−3 |
181 parameters | Absolute structure: Absolute structure known from synthesis |
1 restraint |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O2 | 0.3140 (4) | 0.4452 (4) | 1.0099 (3) | 0.0370 (6) | |
O1 | 0.7363 (4) | 0.4425 (5) | 1.0976 (3) | 0.0390 (6) | |
N1 | 0.8685 (2) | 0.63321 (18) | 0.87612 (15) | 0.0248 (3) | |
H1A | 0.9374 (7) | 0.6423 (7) | 0.7783 (5) | 0.0418 (9) | |
H1B | 1.0086 (8) | 0.5653 (6) | 0.9439 (5) | 0.0440 (10) | |
H1C | 0.8387 (9) | 0.7618 (6) | 0.9167 (5) | 0.0427 (10) | |
N3 | 0.7224 (3) | 0.4469 (2) | 0.38768 (18) | 0.0328 (3) | |
H3 | 0.6923 (9) | 0.4379 (7) | 0.2775 (5) | 0.0466 (10) | |
N2 | 0.9193 (3) | 0.5192 (2) | 0.60256 (16) | 0.0327 (3) | |
C1 | 0.5499 (3) | 0.4701 (2) | 1.0022 (2) | 0.0235 (4) | |
C4 | 0.7008 (3) | 0.4168 (2) | 0.6159 (2) | 0.0259 (4) | |
C6 | 0.5766 (4) | 0.3713 (3) | 0.4831 (2) | 0.0313 (4) | |
H6 | 0.4032 (11) | 0.2932 (9) | 0.4506 (6) | 0.0630 (14) | |
C2 | 0.6168 (3) | 0.5329 (2) | 0.85666 (19) | 0.0216 (3) | |
H2 | 0.4651 (7) | 0.6251 (6) | 0.8071 (5) | 0.0412 (9) | |
C5 | 0.9234 (4) | 0.5343 (3) | 0.4633 (2) | 0.0338 (5) | |
H5 | 1.0673 (11) | 0.6101 (9) | 0.4149 (6) | 0.0662 (16) | |
C3 | 0.6338 (4) | 0.3682 (3) | 0.7597 (2) | 0.0300 (4) | |
H3A | 0.7794 (12) | 0.2737 (7) | 0.8139 (6) | 0.0565 (14) | |
H3B | 0.4455 (12) | 0.2979 (8) | 0.7484 (6) | 0.0641 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0277 (8) | 0.0461 (13) | 0.0394 (17) | 0.0012 (10) | 0.0122 (9) | 0.0168 (12) |
O1 | 0.0322 (10) | 0.0660 (15) | 0.0190 (14) | 0.0030 (12) | 0.0038 (9) | 0.0093 (12) |
N1 | 0.0275 (6) | 0.0273 (7) | 0.0202 (9) | −0.0043 (5) | 0.0053 (6) | −0.0020 (5) |
H1A | 0.0407 (17) | 0.052 (2) | 0.035 (3) | −0.0099 (18) | 0.0123 (18) | 0.004 (2) |
H1B | 0.041 (2) | 0.052 (3) | 0.037 (3) | −0.0032 (17) | −0.0010 (19) | 0.0026 (19) |
H1C | 0.053 (2) | 0.034 (2) | 0.040 (3) | −0.0062 (17) | 0.0053 (19) | −0.0093 (17) |
N3 | 0.0431 (7) | 0.0371 (7) | 0.0190 (10) | 0.0009 (6) | 0.0077 (6) | 0.0008 (6) |
H3 | 0.059 (2) | 0.053 (3) | 0.027 (3) | 0.003 (2) | 0.0039 (19) | −0.002 (2) |
N2 | 0.0377 (6) | 0.0410 (8) | 0.0205 (9) | −0.0086 (6) | 0.0077 (6) | −0.0009 (6) |
C1 | 0.0254 (6) | 0.0284 (9) | 0.0180 (11) | 0.0026 (7) | 0.0070 (6) | 0.0033 (6) |
C4 | 0.0331 (8) | 0.0263 (10) | 0.0193 (12) | −0.0032 (7) | 0.0076 (7) | −0.0015 (7) |
C6 | 0.0375 (10) | 0.0364 (10) | 0.0196 (13) | −0.0054 (8) | 0.0030 (8) | −0.0030 (8) |
H6 | 0.063 (3) | 0.079 (4) | 0.046 (4) | −0.030 (3) | 0.004 (2) | −0.010 (3) |
C2 | 0.0247 (6) | 0.0244 (8) | 0.0164 (10) | −0.0006 (7) | 0.0052 (6) | 0.0026 (7) |
H2 | 0.0376 (17) | 0.044 (2) | 0.042 (3) | 0.0065 (17) | 0.0062 (17) | 0.0107 (19) |
C5 | 0.0404 (9) | 0.0402 (10) | 0.0236 (13) | −0.0048 (9) | 0.0135 (9) | 0.0006 (9) |
H5 | 0.070 (3) | 0.091 (4) | 0.043 (3) | −0.028 (3) | 0.026 (3) | 0.006 (3) |
C3 | 0.0460 (10) | 0.0249 (9) | 0.0204 (12) | −0.0072 (8) | 0.0090 (9) | −0.0008 (7) |
H3A | 0.096 (4) | 0.040 (2) | 0.036 (3) | 0.019 (2) | 0.018 (3) | 0.0076 (19) |
H3B | 0.082 (3) | 0.073 (3) | 0.041 (3) | −0.049 (3) | 0.021 (3) | −0.013 (2) |
O1—C1 | 1.244 (3) | C3—H3A | 1.102 (6) |
N2—C5 | 1.331 (2) | N1—C2 | 1.4899 (19) |
C2—C3 | 1.538 (3) | N3—C6 | 1.379 (3) |
N1—H1A | 1.044 (5) | C4—C6 | 1.374 (3) |
C2—H2 | 1.096 (4) | N1—H1C | 1.046 (5) |
C6—H6 | 1.077 (6) | C3—H3B | 1.098 (7) |
O2—C1 | 1.249 (3) | N2—C4 | 1.384 (2) |
N3—C5 | 1.344 (3) | C1—C2 | 1.544 (3) |
C3—C4 | 1.500 (3) | N3—H3 | 1.038 (5) |
N1—H1B | 1.030 (5) | C5—H5 | 1.086 (6) |
C4—N2—C5 | 105.43 (16) | C3—C2—H2 | 109.6 (3) |
O1—C1—C2 | 116.82 (17) | C4—C3—H3A | 110.2 (3) |
N1—C2—C3 | 110.20 (14) | N2—C5—H5 | 125.0 (4) |
N2—C4—C3 | 120.89 (16) | C4—C6—H6 | 131.2 (4) |
N2—C5—N3 | 111.70 (18) | O1—C1—O2 | 126.8 (2) |
C2—N1—H1A | 109.1 (3) | N1—C2—C1 | 110.08 (14) |
C5—N3—H3 | 124.3 (3) | C2—C3—C4 | 113.31 (16) |
C1—C2—H2 | 109.5 (3) | C3—C4—C6 | 129.64 (16) |
C2—C3—H3B | 107.9 (3) | C2—N1—H1C | 109.0 (3) |
N3—C6—H6 | 122.9 (3) | N1—C2—H2 | 107.8 (2) |
C5—N3—C6 | 107.46 (16) | C2—C3—H3A | 108.5 (3) |
O2—C1—C2 | 116.32 (19) | C4—C3—H3B | 110.0 (3) |
C1—C2—C3 | 109.69 (13) | N3—C5—H5 | 123.3 (3) |
N2—C4—C6 | 109.46 (16) | H1A—N1—H1B | 106.7 (4) |
N3—C6—C4 | 105.95 (17) | H3A—C3—H3B | 106.6 (5) |
C2—N1—H1B | 111.2 (3) | H1A—N1—H1C | 110.9 (4) |
C6—N3—H3 | 128.2 (3) | H1B—N1—H1C | 110.0 (4) |
C5—N2—C4—C3 | 178.91 (17) | O1—C1—C2—N1 | −28.1 (3) |
C6—N3—C5—N2 | 0.5 (2) | O2—C1—C2—C3 | −83.8 (2) |
O1—C1—C2—C3 | 93.4 (2) | C2—C3—C4—N2 | 53.9 (2) |
N1—C2—C3—C4 | −58.10 (19) | C3—C4—C6—N3 | −178.46 (17) |
C2—C3—C4—C6 | −127.7 (2) | H1A—N1—C2—H2 | −76.7 (4) |
H1A—N1—C2—C1 | 163.9 (3) | H1B—N1—C2—H2 | 165.9 (4) |
H1B—N1—C2—C1 | 46.6 (3) | H1C—N1—C2—H2 | 44.5 (4) |
H1C—N1—C2—C1 | −74.9 (3) | H3—N3—C5—N2 | −177.8 (4) |
C4—N2—C5—H5 | 178.2 (5) | H3—N3—C6—C4 | 177.9 (4) |
H3—N3—C5—H5 | 3.5 (6) | O2—C1—C2—H2 | 36.5 (3) |
H3—N3—C6—H6 | −1.7 (6) | N1—C2—C3—H3A | 64.6 (4) |
C5—N2—C4—C6 | 0.2 (2) | C1—C2—C3—H3B | 58.4 (4) |
C5—N3—C6—C4 | −0.4 (2) | H2—C2—C3—H3B | −61.8 (4) |
O2—C1—C2—N1 | 154.78 (19) | H3B—C3—C4—N2 | 174.8 (4) |
C1—C2—C3—C4 | −179.46 (14) | C3—C4—C6—H6 | 1.1 (6) |
N2—C4—C6—N3 | 0.2 (2) | N1—C2—C3—H3B | 179.8 (3) |
H1A—N1—C2—C3 | 42.8 (3) | H2—C2—C3—C4 | 60.4 (3) |
H1B—N1—C2—C3 | −74.6 (3) | H3A—C3—C4—N2 | −67.9 (4) |
H1C—N1—C2—C3 | 164.0 (3) | H3B—C3—C4—C6 | −6.7 (4) |
C6—N3—C5—H5 | −178.1 (4) | C1—C2—C3—H3A | −56.7 (4) |
C5—N3—C6—H6 | −180.0 (5) | H2—C2—C3—H3A | −176.9 (4) |
O1—C1—C2—H2 | −146.4 (3) | H3A—C3—C4—C6 | 110.5 (4) |
C4—N2—C5—N3 | −0.4 (2) | N2—C4—C6—H6 | 179.7 (5) |
C6H9N3O2 | Dx = 1.476 Mg m−3 |
Mr = 155.16 | Neutron radiation, λ = 0.80 Å |
Orthorhombic, P212121 | Cell parameters from 7499 reflections |
a = 5.1498 (2) Å | θ = 3.0–36.3° |
b = 7.1902 (2) Å | µ = 0.0 mm−1 |
c = 18.8503 (6) Å | T = 5 K |
V = 697.99 (4) Å3 | Needle, colourless |
Z = 4 | 0.35 × 0.30 × 0.15 mm |
F(000) = 184 |
KOALA diffractometer | Rint = 0.188 |
Radiation source: nuclear reactor, OPAL reactor, ANSTO, Lucas Heights, Australia | θmax = 71.2° |
Laue scans | h = −8→8 |
33762 measured reflections | k = −12→11 |
1375 independent reflections | l = −28→28 |
1133 reflections with I > 2σ(I) |
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.048 | w = 1/[σ2(Fo2) + (0.030P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.069 | (Δ/σ)max < 0.001 |
S = 1.15 | Δρmax = 1.49 e Å−3 |
1375 reflections | Δρmin = −1.34 e Å−3 |
181 parameters | Absolute structure: Absolute structure known from synthesis |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O2 | 0.3252 (3) | 0.4947 (3) | 0.23962 (11) | 0.0082 (4) | |
O1 | 0.7328 (3) | 0.4917 (3) | 0.19749 (13) | 0.0081 (4) | |
N1 | 0.9182 (2) | 0.31158 (16) | 0.31208 (8) | 0.0076 (3) | |
N3 | 0.86952 (19) | 0.50364 (16) | 0.55338 (8) | 0.0074 (2) | |
N2 | 1.0322 (2) | 0.43916 (15) | 0.44681 (8) | 0.0076 (2) | |
C4 | 0.8030 (3) | 0.5395 (2) | 0.43874 (10) | 0.0064 (3) | |
C1 | 0.5658 (3) | 0.4701 (2) | 0.24520 (9) | 0.0062 (3) | |
C2 | 0.6666 (3) | 0.4137 (2) | 0.31917 (10) | 0.0050 (3) | |
C6 | 0.7008 (3) | 0.5791 (2) | 0.50449 (10) | 0.0065 (3) | |
C5 | 1.0628 (3) | 0.4205 (2) | 0.51652 (10) | 0.0076 (3) | |
C3 | 0.7027 (3) | 0.5874 (2) | 0.36619 (10) | 0.0073 (3) | |
H1B | 1.0426 (7) | 0.3791 (5) | 0.2769 (2) | 0.0194 (8) | |
H1C | 0.8794 (7) | 0.1770 (5) | 0.2951 (2) | 0.0205 (9) | |
H1A | 1.0122 (6) | 0.3102 (6) | 0.3610 (2) | 0.0177 (8) | |
H3 | 0.8478 (6) | 0.5046 (6) | 0.6090 (2) | 0.0193 (8) | |
H2 | 0.5255 (6) | 0.3176 (5) | 0.3444 (2) | 0.0169 (7) | |
H6 | 0.5285 (7) | 0.6556 (6) | 0.5201 (3) | 0.0247 (9) | |
H5 | 1.2224 (7) | 0.3478 (6) | 0.5415 (2) | 0.0240 (9) | |
H3A | 0.8371 (8) | 0.6849 (5) | 0.3397 (2) | 0.0234 (9) | |
H3B | 0.5139 (7) | 0.6563 (6) | 0.3713 (3) | 0.0236 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0045 (7) | 0.0086 (8) | 0.0114 (12) | −0.0006 (6) | −0.0006 (6) | 0.0015 (8) |
O1 | 0.0049 (6) | 0.0116 (8) | 0.0077 (12) | 0.0000 (6) | 0.0007 (5) | 0.0005 (7) |
N1 | 0.0069 (4) | 0.0063 (5) | 0.0096 (8) | 0.0011 (4) | −0.0004 (4) | −0.0009 (4) |
N3 | 0.0071 (4) | 0.0087 (5) | 0.0063 (8) | 0.0001 (4) | −0.0001 (4) | −0.0012 (5) |
N2 | 0.0063 (4) | 0.0078 (5) | 0.0087 (7) | 0.0018 (3) | 0.0003 (4) | −0.0011 (5) |
C4 | 0.0065 (5) | 0.0066 (6) | 0.0062 (10) | 0.0005 (5) | −0.0005 (5) | −0.0010 (6) |
C1 | 0.0053 (6) | 0.0053 (6) | 0.0079 (10) | −0.0001 (5) | −0.0001 (5) | 0.0005 (6) |
C2 | 0.0042 (6) | 0.0055 (6) | 0.0053 (10) | 0.0006 (5) | −0.0002 (5) | −0.0007 (6) |
C6 | 0.0057 (6) | 0.0078 (6) | 0.0060 (10) | 0.0015 (5) | −0.0009 (5) | −0.0009 (6) |
C5 | 0.0067 (6) | 0.0085 (7) | 0.0078 (10) | 0.0018 (6) | 0.0000 (6) | 0.0002 (6) |
C3 | 0.0082 (6) | 0.0050 (6) | 0.0086 (10) | 0.0018 (5) | −0.0015 (6) | −0.0006 (6) |
H1B | 0.0186 (16) | 0.0177 (15) | 0.022 (3) | 0.0008 (13) | 0.0044 (15) | 0.0019 (14) |
H1C | 0.0211 (15) | 0.0122 (15) | 0.028 (3) | 0.0009 (12) | −0.0011 (14) | −0.0077 (15) |
H1A | 0.0156 (15) | 0.0229 (17) | 0.015 (2) | 0.0030 (12) | −0.0028 (13) | 0.0002 (16) |
H3 | 0.0202 (15) | 0.0236 (16) | 0.014 (2) | 0.0019 (14) | −0.0009 (13) | 0.0000 (16) |
H2 | 0.0145 (14) | 0.0191 (15) | 0.017 (2) | −0.0031 (12) | 0.0006 (13) | 0.0011 (15) |
H6 | 0.0178 (16) | 0.0281 (19) | 0.028 (3) | 0.0095 (14) | 0.0026 (15) | −0.0035 (18) |
H5 | 0.0201 (16) | 0.030 (2) | 0.022 (3) | 0.0099 (14) | −0.0060 (15) | 0.0042 (17) |
H3A | 0.0277 (18) | 0.0184 (16) | 0.024 (3) | −0.0071 (15) | −0.0020 (16) | 0.0056 (16) |
H3B | 0.0175 (16) | 0.030 (2) | 0.023 (3) | 0.0119 (13) | −0.0027 (15) | −0.0028 (17) |
O1—C1 | 1.254 (3) | C3—H3A | 1.105 (4) |
N2—C5 | 1.330 (2) | N1—C2 | 1.4953 (19) |
C2—C3 | 1.543 (2) | N3—C6 | 1.378 (2) |
N1—H1A | 1.042 (4) | C4—C6 | 1.376 (3) |
C2—H2 | 1.110 (4) | N1—H1C | 1.039 (4) |
C6—H6 | 1.085 (4) | C3—H3B | 1.096 (4) |
O2—C1 | 1.256 (2) | N2—C4 | 1.3917 (18) |
N3—C5 | 1.353 (2) | C1—C2 | 1.542 (2) |
C3—C4 | 1.502 (3) | N3—H3 | 1.054 (4) |
N1—H1B | 1.042 (4) | C5—H5 | 1.082 (4) |
C4—N2—C5 | 105.11 (13) | C3—C2—H2 | 109.7 (2) |
O1—C1—C2 | 116.75 (15) | C4—C3—H3A | 110.0 (2) |
N1—C2—C3 | 110.15 (12) | N2—C5—H5 | 124.7 (2) |
N2—C4—C3 | 120.67 (15) | C4—C6—H6 | 131.5 (3) |
N2—C5—N3 | 112.06 (13) | O1—C1—O2 | 126.80 (19) |
C2—N1—H1A | 109.2 (2) | N1—C2—C1 | 109.88 (14) |
C5—N3—H3 | 126.3 (2) | C2—C3—C4 | 112.27 (13) |
C1—C2—H2 | 109.3 (2) | C3—C4—C6 | 129.87 (14) |
C2—C3—H3B | 108.0 (3) | C2—N1—H1C | 108.6 (2) |
N3—C6—H6 | 122.3 (3) | N1—C2—H2 | 107.5 (2) |
C5—N3—C6 | 107.12 (15) | C2—C3—H3A | 109.3 (2) |
O2—C1—C2 | 116.41 (16) | C4—C3—H3B | 109.2 (3) |
C1—C2—C3 | 110.31 (12) | N3—C5—H5 | 123.3 (3) |
N2—C4—C6 | 109.46 (15) | H1A—N1—H1B | 106.4 (3) |
N3—C6—C4 | 106.24 (13) | H3A—C3—H3B | 108.0 (3) |
C2—N1—H1B | 111.2 (2) | H1A—N1—H1C | 110.7 (3) |
C6—N3—H3 | 126.6 (2) | H1B—N1—H1C | 110.9 (3) |
C5—N2—C4—C3 | −179.65 (13) | O1—C1—C2—N1 | −26.6 (2) |
C6—N3—C5—N2 | 0.80 (16) | O2—C1—C2—C3 | −83.06 (19) |
O1—C1—C2—C3 | 94.99 (19) | C2—C3—C4—N2 | 55.75 (18) |
N1—C2—C3—C4 | −58.05 (18) | C3—C4—C6—N3 | −179.92 (15) |
C2—C3—C4—C6 | −123.87 (17) | H1A—N1—C2—H2 | −78.5 (3) |
H1A—N1—C2—C1 | 162.7 (3) | H1B—N1—C2—H2 | 164.4 (3) |
H1B—N1—C2—C1 | 45.6 (3) | H1C—N1—C2—H2 | 42.3 (3) |
H1C—N1—C2—C1 | −76.6 (3) | H3—N3—C5—N2 | 178.1 (3) |
C4—N2—C5—H5 | 179.5 (3) | H3—N3—C6—C4 | −178.0 (3) |
H3—N3—C5—H5 | −1.9 (4) | O2—C1—C2—H2 | 37.6 (3) |
H3—N3—C6—H6 | 3.4 (4) | N1—C2—C3—H3A | 64.2 (3) |
C5—N2—C4—C6 | 0.05 (16) | C1—C2—C3—H3B | 60.0 (3) |
C5—N3—C6—C4 | −0.72 (16) | H2—C2—C3—H3B | −60.5 (4) |
O2—C1—C2—N1 | 155.31 (16) | H3B—C3—C4—N2 | 175.6 (3) |
C1—C2—C3—C4 | −179.52 (13) | C3—C4—C6—H6 | −1.5 (4) |
N2—C4—C6—N3 | 0.42 (16) | N1—C2—C3—H3B | −178.5 (3) |
H1A—N1—C2—C3 | 40.9 (3) | H2—C2—C3—C4 | 60.0 (3) |
H1B—N1—C2—C3 | −76.1 (3) | H3A—C3—C4—N2 | −66.1 (3) |
H1C—N1—C2—C3 | 161.7 (3) | H3B—C3—C4—C6 | −4.1 (3) |
C6—N3—C5—H5 | −179.2 (3) | C1—C2—C3—H3A | −57.2 (3) |
C5—N3—C6—H6 | −179.3 (3) | H2—C2—C3—H3A | −177.7 (3) |
O1—C1—C2—H2 | −144.3 (3) | H3A—C3—C4—C6 | 114.3 (3) |
C4—N2—C5—N3 | −0.53 (16) | N2—C4—C6—H6 | 178.8 (3) |
C6H9N3O2 | Dx = 1.470 Mg m−3 |
Mr = 155.16 | Neutron radiation, λ = 0.80 Å |
Orthorhombic, P212121 | Cell parameters from 6123 reflections |
a = 5.1521 (10) Å | θ = 3.0–36.0° |
b = 7.2228 (2) Å | µ = 0.0 mm−1 |
c = 18.8440 (6) Å | T = 105 K |
V = 701.23 (14) Å3 | Needle, colourless |
Z = 4 | 0.35 × 0.30 × 0.15 mm |
F(000) = 184 |
KOALA diffractometer | Rint = 0.214 |
Radiation source: nuclear reactor, OPAL reactor, ANSTO, Lucas Heights, Australia | θmax = 71.2° |
Laue scans | h = −8→8 |
32598 measured reflections | k = −12→11 |
1361 independent reflections | l = −28→28 |
1061 reflections with I > 2σ(I) |
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.052 | w = 1/[σ2(Fo2) + (0.030P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.074 | (Δ/σ)max < 0.001 |
S = 1.15 | Δρmax = 1.27 e Å−3 |
1361 reflections | Δρmin = −1.10 e Å−3 |
181 parameters | Absolute structure: Absolute structure known from synthesis |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O2 | 0.3242 (4) | 0.4979 (3) | 0.24007 (13) | 0.0147 (5) | |
O1 | 0.7306 (4) | 0.4942 (3) | 0.19789 (14) | 0.0151 (5) | |
N1 | 0.9167 (2) | 0.31345 (17) | 0.31167 (9) | 0.0114 (3) | |
H1B | 1.0391 (8) | 0.3799 (6) | 0.2768 (3) | 0.0239 (9) | |
H1C | 0.8786 (8) | 0.1799 (5) | 0.2943 (3) | 0.0253 (10) | |
H1A | 1.0097 (7) | 0.3110 (6) | 0.3610 (3) | 0.0239 (9) | |
N3 | 0.8707 (2) | 0.50253 (18) | 0.55332 (9) | 0.0127 (3) | |
H3 | 0.8483 (7) | 0.5046 (6) | 0.6092 (2) | 0.0248 (9) | |
N2 | 1.0323 (2) | 0.43948 (18) | 0.44686 (9) | 0.0130 (3) | |
C4 | 0.8041 (3) | 0.5392 (2) | 0.43910 (11) | 0.0110 (4) | |
C1 | 0.5648 (3) | 0.4728 (2) | 0.24541 (10) | 0.0108 (4) | |
C2 | 0.6660 (3) | 0.4161 (2) | 0.31938 (11) | 0.0088 (4) | |
H2 | 0.5255 (7) | 0.3212 (6) | 0.3440 (2) | 0.0222 (9) | |
C6 | 0.7018 (4) | 0.5786 (3) | 0.50489 (11) | 0.0120 (4) | |
H6 | 0.5312 (8) | 0.6534 (7) | 0.5202 (3) | 0.0322 (11) | |
C5 | 1.0634 (3) | 0.4201 (3) | 0.51659 (12) | 0.0136 (4) | |
H5 | 1.2222 (8) | 0.3459 (7) | 0.5419 (3) | 0.0317 (11) | |
C3 | 0.7043 (4) | 0.5885 (2) | 0.36664 (12) | 0.0129 (4) | |
H3A | 0.8376 (10) | 0.6834 (6) | 0.3400 (3) | 0.0310 (11) | |
H3B | 0.5166 (8) | 0.6576 (7) | 0.3708 (3) | 0.0328 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0112 (9) | 0.0174 (10) | 0.0156 (14) | 0.0003 (8) | −0.0018 (7) | 0.0040 (10) |
O1 | 0.0096 (8) | 0.0235 (10) | 0.0122 (14) | −0.0012 (8) | 0.0006 (7) | 0.0021 (9) |
N1 | 0.0103 (5) | 0.0124 (6) | 0.0115 (9) | 0.0022 (4) | −0.0003 (5) | −0.0003 (5) |
H1B | 0.0246 (19) | 0.0253 (19) | 0.022 (3) | 0.0030 (15) | 0.0085 (17) | 0.0031 (16) |
H1C | 0.0304 (19) | 0.0159 (17) | 0.029 (3) | 0.0028 (14) | −0.0022 (17) | −0.0046 (17) |
H1A | 0.0211 (18) | 0.031 (2) | 0.019 (3) | 0.0051 (14) | −0.0030 (16) | 0.0010 (19) |
N3 | 0.0149 (5) | 0.0152 (6) | 0.0079 (9) | 0.0004 (5) | 0.0006 (4) | −0.0009 (6) |
H3 | 0.0282 (18) | 0.034 (2) | 0.012 (3) | −0.0018 (18) | −0.0025 (15) | 0.0039 (19) |
N2 | 0.0135 (5) | 0.0151 (6) | 0.0105 (8) | 0.0033 (4) | 0.0000 (5) | −0.0012 (6) |
C4 | 0.0117 (6) | 0.0100 (7) | 0.0114 (12) | 0.0012 (6) | 0.0002 (7) | 0.0002 (7) |
C1 | 0.0088 (7) | 0.0111 (7) | 0.0126 (12) | −0.0007 (7) | −0.0019 (6) | 0.0000 (7) |
C2 | 0.0087 (7) | 0.0081 (7) | 0.0096 (11) | 0.0009 (6) | 0.0003 (6) | 0.0013 (7) |
H2 | 0.0216 (17) | 0.0230 (18) | 0.022 (3) | −0.0048 (15) | 0.0016 (16) | 0.0035 (17) |
C6 | 0.0111 (7) | 0.0150 (8) | 0.0098 (12) | 0.0017 (7) | 0.0004 (6) | −0.0028 (7) |
H6 | 0.0252 (19) | 0.042 (3) | 0.030 (3) | 0.0156 (18) | 0.0021 (19) | −0.008 (2) |
C5 | 0.0133 (7) | 0.0162 (8) | 0.0112 (12) | 0.0041 (7) | −0.0033 (7) | 0.0002 (8) |
H5 | 0.0270 (19) | 0.039 (2) | 0.029 (3) | 0.0138 (17) | −0.0068 (19) | 0.006 (2) |
C3 | 0.0155 (8) | 0.0099 (8) | 0.0133 (12) | 0.0019 (7) | −0.0034 (7) | −0.0007 (8) |
H3A | 0.041 (2) | 0.0249 (19) | 0.027 (3) | −0.0104 (19) | −0.003 (2) | 0.0066 (19) |
H3B | 0.027 (2) | 0.038 (2) | 0.033 (3) | 0.0193 (17) | −0.009 (2) | −0.008 (2) |
O1—C1 | 1.247 (3) | C3—H3A | 1.093 (5) |
N2—C5 | 1.331 (3) | N1—C2 | 1.4964 (19) |
C2—C3 | 1.544 (2) | N3—C6 | 1.376 (3) |
N1—H1A | 1.046 (6) | C4—C6 | 1.377 (3) |
C2—H2 | 1.100 (4) | N1—H1C | 1.037 (4) |
C6—H6 | 1.071 (5) | C3—H3B | 1.091 (5) |
O2—C1 | 1.257 (3) | N2—C4 | 1.3865 (19) |
N3—C5 | 1.349 (2) | C1—C2 | 1.544 (3) |
C3—C4 | 1.502 (3) | N3—H3 | 1.059 (4) |
N1—H1B | 1.030 (5) | C5—H5 | 1.088 (5) |
C4—N2—C5 | 105.12 (15) | C3—C2—H2 | 110.1 (3) |
O1—C1—C2 | 116.74 (17) | C4—C3—H3A | 110.6 (3) |
N1—C2—C3 | 110.21 (14) | N2—C5—H5 | 125.1 (3) |
N2—C4—C3 | 120.62 (17) | C4—C6—H6 | 131.4 (4) |
N2—C5—N3 | 111.81 (15) | O1—C1—O2 | 126.9 (2) |
C2—N1—H1A | 108.5 (3) | N1—C2—C1 | 109.59 (15) |
C5—N3—H3 | 126.6 (3) | C2—C3—C4 | 112.15 (13) |
C1—C2—H2 | 108.9 (2) | C3—C4—C6 | 129.69 (16) |
C2—C3—H3B | 107.3 (3) | C2—N1—H1C | 109.2 (2) |
N3—C6—H6 | 122.8 (4) | N1—C2—H2 | 107.5 (2) |
C5—N3—C6 | 107.55 (17) | C2—C3—H3A | 108.8 (3) |
O2—C1—C2 | 116.34 (18) | C4—C3—H3B | 110.3 (3) |
C1—C2—C3 | 110.50 (13) | N3—C5—H5 | 123.1 (3) |
N2—C4—C6 | 109.69 (17) | H1A—N1—H1B | 107.1 (4) |
N3—C6—C4 | 105.82 (17) | H3A—C3—H3B | 107.7 (4) |
C2—N1—H1B | 111.1 (3) | H1A—N1—H1C | 110.6 (4) |
C6—N3—H3 | 125.8 (2) | H1B—N1—H1C | 110.4 (4) |
C5—N2—C4—C3 | −179.96 (15) | O1—C1—C2—N1 | −26.9 (2) |
C6—N3—C5—N2 | 0.7 (2) | O2—C1—C2—C3 | −83.2 (2) |
O1—C1—C2—C3 | 94.7 (2) | C2—C3—C4—N2 | 56.3 (2) |
N1—C2—C3—C4 | −58.4 (2) | C3—C4—C6—N3 | −179.61 (15) |
C2—C3—C4—C6 | −123.8 (2) | H1A—N1—C2—H2 | −78.6 (4) |
H1A—N1—C2—C1 | 163.2 (3) | H1B—N1—C2—H2 | 163.9 (4) |
H1B—N1—C2—C1 | 45.7 (3) | H1C—N1—C2—H2 | 42.0 (4) |
H1C—N1—C2—C1 | −76.2 (4) | H3—N3—C5—N2 | 178.6 (3) |
C4—N2—C5—H5 | 178.8 (4) | H3—N3—C6—C4 | −178.5 (3) |
H3—N3—C5—H5 | −0.7 (5) | O2—C1—C2—H2 | 37.9 (3) |
H3—N3—C6—H6 | 2.5 (5) | N1—C2—C3—H3A | 64.2 (3) |
C5—N2—C4—C6 | 0.15 (19) | C1—C2—C3—H3B | 59.1 (4) |
C5—N3—C6—C4 | −0.6 (2) | H2—C2—C3—H3B | −61.3 (4) |
O2—C1—C2—N1 | 155.17 (16) | H3B—C3—C4—N2 | 175.8 (3) |
C1—C2—C3—C4 | −179.71 (14) | C3—C4—C6—H6 | −0.7 (5) |
N2—C4—C6—N3 | 0.3 (2) | N1—C2—C3—H3B | −179.7 (3) |
H1A—N1—C2—C3 | 41.4 (3) | H2—C2—C3—C4 | 60.0 (3) |
H1B—N1—C2—C3 | −76.1 (4) | H3A—C3—C4—N2 | −65.2 (3) |
H1C—N1—C2—C3 | 162.0 (4) | H3B—C3—C4—C6 | −4.3 (4) |
C6—N3—C5—H5 | −178.6 (4) | C1—C2—C3—H3A | −57.1 (3) |
C5—N3—C6—H6 | −179.6 (4) | H2—C2—C3—H3A | −177.5 (4) |
O1—C1—C2—H2 | −144.2 (3) | H3A—C3—C4—C6 | 114.6 (3) |
C4—N2—C5—N3 | −0.53 (19) | N2—C4—C6—H6 | 179.2 (4) |
C6H9N3O2 | Dx = 1.442 Mg m−3 |
Mr = 155.16 | Neutron radiation, λ = 0.80 Å |
Orthorhombic, P212121 | Cell parameters from 4787 reflections |
a = 5.1690 (3) Å | θ = 3.0–32.3° |
b = 7.3430 (5) Å | µ = 0.0 mm−1 |
c = 18.8317 (13) Å | T = 295 K |
V = 714.78 (8) Å3 | Needle, colourless |
Z = 4 | 0.35 × 0.30 × 0.15 mm |
F(000) = 184 |
KOALA diffractometer | Rint = 0.237 |
Radiation source: nuclear reactor, OPAL reactor, ANSTO, Lucas Heights, Australia | θmax = 70.9° |
Laue scans | h = −7→7 |
32190 measured reflections | k = −11→11 |
1104 independent reflections | l = −26→26 |
781 reflections with I > 2σ(I) |
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.054 | w = 1/[σ2(Fo2) + (0.030P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.078 | (Δ/σ)max < 0.001 |
S = 1.19 | Δρmax = 0.67 e Å−3 |
1104 reflections | Δρmin = −0.65 e Å−3 |
181 parameters | Absolute structure: Absolute structure known from synthesis |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O2 | 0.3241 (6) | 0.5093 (4) | 0.24197 (18) | 0.0374 (8) | |
O1 | 0.7255 (6) | 0.5056 (5) | 0.1988 (2) | 0.0399 (8) | |
N1 | 0.9129 (4) | 0.3213 (2) | 0.31058 (13) | 0.0274 (4) | |
H1B | 1.0310 (11) | 0.3850 (8) | 0.2762 (4) | 0.0461 (14) | |
H1C | 0.8690 (11) | 0.1909 (8) | 0.2926 (3) | 0.0450 (14) | |
H1A | 1.0058 (9) | 0.3154 (8) | 0.3593 (3) | 0.0406 (13) | |
N3 | 0.8748 (3) | 0.4997 (3) | 0.55358 (12) | 0.0322 (4) | |
H3 | 0.8527 (11) | 0.4994 (8) | 0.6087 (4) | 0.0483 (14) | |
N2 | 1.0323 (3) | 0.4398 (2) | 0.44699 (11) | 0.0334 (5) | |
C4 | 0.8077 (5) | 0.5400 (3) | 0.43942 (14) | 0.0265 (5) | |
C1 | 0.5626 (5) | 0.4821 (3) | 0.24611 (13) | 0.0258 (6) | |
C2 | 0.6649 (4) | 0.4240 (3) | 0.31964 (13) | 0.0229 (5) | |
H2 | 0.5241 (9) | 0.3313 (8) | 0.3445 (3) | 0.0407 (13) | |
C6 | 0.7065 (5) | 0.5766 (4) | 0.50536 (15) | 0.0329 (7) | |
H6 | 0.5344 (12) | 0.6503 (10) | 0.5214 (4) | 0.0586 (17) | |
C5 | 1.0649 (5) | 0.4188 (4) | 0.51627 (16) | 0.0341 (6) | |
H5 | 1.2206 (13) | 0.3431 (10) | 0.5413 (4) | 0.0606 (18) | |
C3 | 0.7079 (6) | 0.5905 (3) | 0.36726 (15) | 0.0311 (6) | |
H3A | 0.8392 (15) | 0.6853 (9) | 0.3410 (4) | 0.0595 (19) | |
H3B | 0.5253 (13) | 0.6609 (9) | 0.3727 (4) | 0.0627 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0230 (14) | 0.0439 (19) | 0.045 (2) | 0.0002 (13) | −0.0064 (12) | 0.0150 (16) |
O1 | 0.0304 (14) | 0.063 (2) | 0.027 (2) | −0.0015 (14) | −0.0001 (11) | 0.0094 (16) |
N1 | 0.0278 (9) | 0.0278 (9) | 0.0266 (14) | 0.0061 (7) | −0.0012 (9) | −0.0019 (9) |
H1B | 0.044 (3) | 0.051 (3) | 0.044 (4) | 0.011 (3) | 0.005 (3) | 0.001 (3) |
H1C | 0.052 (3) | 0.037 (3) | 0.046 (4) | 0.004 (2) | −0.006 (3) | −0.006 (3) |
H1A | 0.033 (3) | 0.055 (3) | 0.034 (4) | 0.013 (2) | 0.001 (2) | 0.001 (3) |
N3 | 0.0383 (10) | 0.0378 (10) | 0.0205 (13) | −0.0013 (8) | −0.0002 (7) | −0.0017 (9) |
H3 | 0.060 (4) | 0.055 (3) | 0.030 (4) | −0.003 (3) | −0.005 (3) | 0.001 (3) |
N2 | 0.0315 (9) | 0.0418 (11) | 0.0270 (13) | 0.0077 (7) | −0.0007 (8) | 0.0010 (9) |
C4 | 0.0328 (11) | 0.0250 (12) | 0.0217 (16) | 0.0009 (9) | −0.0026 (10) | −0.0027 (11) |
C1 | 0.0235 (11) | 0.0296 (12) | 0.0242 (17) | 0.0007 (10) | −0.0013 (9) | 0.0027 (11) |
C2 | 0.0244 (11) | 0.0242 (11) | 0.0202 (15) | 0.0011 (9) | 0.0020 (9) | 0.0028 (9) |
H2 | 0.031 (2) | 0.053 (3) | 0.039 (4) | −0.011 (2) | 0.005 (2) | 0.007 (3) |
C6 | 0.0330 (13) | 0.0395 (15) | 0.0262 (18) | 0.0055 (12) | 0.0022 (11) | −0.0054 (12) |
H6 | 0.050 (3) | 0.075 (4) | 0.051 (4) | 0.026 (3) | 0.007 (3) | −0.007 (3) |
C5 | 0.0343 (13) | 0.0453 (16) | 0.0226 (17) | 0.0068 (13) | −0.0041 (12) | 0.0002 (13) |
H5 | 0.058 (4) | 0.077 (4) | 0.047 (5) | 0.022 (3) | −0.019 (3) | 0.006 (3) |
C3 | 0.0452 (15) | 0.0224 (12) | 0.0257 (18) | 0.0073 (11) | −0.0072 (12) | −0.0015 (11) |
H3A | 0.093 (5) | 0.047 (3) | 0.038 (4) | −0.022 (4) | −0.010 (4) | 0.010 (3) |
H3B | 0.069 (5) | 0.065 (4) | 0.054 (5) | 0.028 (3) | −0.008 (4) | −0.017 (3) |
O1—C1 | 1.238 (4) | C3—H3A | 1.091 (8) |
N2—C5 | 1.325 (4) | N1—C2 | 1.497 (3) |
C2—C3 | 1.532 (3) | N3—C6 | 1.379 (3) |
N1—H1A | 1.037 (6) | C4—C6 | 1.374 (4) |
C2—H2 | 1.101 (6) | N1—H1C | 1.041 (6) |
C6—H6 | 1.084 (7) | C3—H3B | 1.081 (7) |
O2—C1 | 1.251 (4) | N2—C4 | 1.382 (3) |
N3—C5 | 1.346 (3) | C1—C2 | 1.542 (3) |
C3—C4 | 1.500 (4) | N3—H3 | 1.044 (8) |
N1—H1B | 1.005 (7) | C5—H5 | 1.086 (8) |
C4—N2—C5 | 105.7 (2) | C3—C2—H2 | 109.9 (4) |
O1—C1—C2 | 116.8 (3) | C4—C3—H3A | 110.8 (5) |
N1—C2—C3 | 110.15 (19) | N2—C5—H5 | 125.6 (5) |
N2—C4—C3 | 120.9 (2) | C4—C6—H6 | 131.4 (5) |
N2—C5—N3 | 111.7 (2) | O1—C1—O2 | 127.1 (3) |
C2—N1—H1A | 108.5 (3) | N1—C2—C1 | 109.3 (2) |
C5—N3—H3 | 126.7 (4) | C2—C3—C4 | 112.51 (19) |
C1—C2—H2 | 109.0 (3) | C3—C4—C6 | 129.8 (2) |
C2—C3—H3B | 108.1 (4) | C2—N1—H1C | 108.3 (4) |
N3—C6—H6 | 122.6 (5) | N1—C2—H2 | 107.6 (3) |
C5—N3—C6 | 107.3 (2) | C2—C3—H3A | 109.5 (4) |
O2—C1—C2 | 116.0 (2) | C4—C3—H3B | 109.4 (5) |
C1—C2—C3 | 110.76 (19) | N3—C5—H5 | 122.7 (5) |
N2—C4—C6 | 109.3 (2) | H1A—N1—H1B | 108.0 (5) |
N3—C6—C4 | 106.0 (2) | H3A—C3—H3B | 106.3 (6) |
C2—N1—H1B | 111.0 (4) | H1A—N1—H1C | 110.5 (5) |
C6—N3—H3 | 125.9 (4) | H1B—N1—H1C | 110.6 (5) |
C5—N2—C4—C3 | −179.9 (2) | O1—C1—C2—N1 | −28.0 (3) |
C6—N3—C5—N2 | 0.6 (3) | O2—C1—C2—C3 | −83.0 (3) |
O1—C1—C2—C3 | 93.5 (3) | C2—C3—C4—N2 | 56.3 (3) |
N1—C2—C3—C4 | −58.9 (3) | C3—C4—C6—N3 | −179.9 (2) |
C2—C3—C4—C6 | −122.8 (3) | H1A—N1—C2—H2 | −77.7 (5) |
H1A—N1—C2—C1 | 164.0 (4) | H1B—N1—C2—H2 | 163.8 (6) |
H1B—N1—C2—C1 | 45.5 (5) | H1C—N1—C2—H2 | 42.3 (5) |
H1C—N1—C2—C1 | −76.0 (4) | H3—N3—C5—N2 | 177.9 (4) |
C4—N2—C5—H5 | 178.2 (5) | H3—N3—C6—C4 | −178.2 (5) |
H3—N3—C5—H5 | −0.5 (7) | O2—C1—C2—H2 | 38.1 (4) |
H3—N3—C6—H6 | 2.4 (7) | N1—C2—C3—H3A | 64.7 (5) |
C5—N2—C4—C6 | −0.5 (3) | C1—C2—C3—H3B | 59.1 (5) |
C5—N3—C6—C4 | −0.9 (3) | H2—C2—C3—H3B | −61.4 (6) |
O2—C1—C2—N1 | 155.5 (2) | H3B—C3—C4—N2 | 176.5 (4) |
C1—C2—C3—C4 | −180.0 (2) | C3—C4—C6—H6 | −0.6 (7) |
N2—C4—C6—N3 | 0.9 (3) | N1—C2—C3—H3B | −179.9 (5) |
H1A—N1—C2—C3 | 42.1 (4) | H2—C2—C3—C4 | 59.5 (4) |
H1B—N1—C2—C3 | −76.4 (5) | H3A—C3—C4—N2 | −66.6 (5) |
H1C—N1—C2—C3 | 162.1 (4) | H3B—C3—C4—C6 | −2.7 (5) |
C6—N3—C5—H5 | −177.7 (5) | C1—C2—C3—H3A | −56.3 (5) |
C5—N3—C6—H6 | 179.7 (5) | H2—C2—C3—H3A | −176.9 (5) |
O1—C1—C2—H2 | −145.4 (4) | H3A—C3—C4—C6 | 114.2 (5) |
C4—N2—C5—N3 | −0.1 (3) | N2—C4—C6—H6 | −179.8 (6) |
C6H9N3O2 | F(000) = 164.036 |
Mr = 155.16 | Dx = 1.464 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.1651 (2) Å | Cell parameters from 4301 reflections |
b = 7.2324 (2) Å | θ = 3.6–30.5° |
c = 9.4957 (3) Å | µ = 0.11 mm−1 |
β = 97.065 (2)° | T = 5 K |
V = 352.03 (2) Å3 | Plate, colourless |
Z = 2 | 0.2 × 0.2 × 0.1 mm |
Bruker APEX-II CCD diffractometer | 2138 independent reflections |
Radiation source: rotating anode, Bruker TXS with Helios Optics | 2087 reflections with I ≥ 2u(I) |
Multilayer optics monochromator | Rint = 0.025 |
φ scans | θmax = 30.5°, θmin = 3.6° |
Absorption correction: multi-scan SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 | h = −7→7 |
Tmin = 0.687, Tmax = 0.746 | k = −10→10 |
11118 measured reflections | l = −13→13 |
Refinement on F2 | 0 constraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.017 | w = 1/[σ2(Fo2) + (0.0081P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.029 | (Δ/σ)max = 0.001 |
S = 1.28 | Δρmax = 0.12 e Å−3 |
2138 reflections | Δρmin = −0.10 e Å−3 |
181 parameters | Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881. |
100 restraints | Absolute structure parameter: 0.4 (9) |
Refinement. Refinement using NoSpherA2, an implementation of NOn-SPHERical Atom-form-factors in Olex2. Please cite: F. Kleemiss et al. DOI 10.1039/D0SC05526C - 2020 NoSpherA2 implementation of HAR makes use of tailor-made aspherical atomic form factors calculated on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from spherical-atom form factors. The ED is calculated from a gaussian basis set single determinant SCF wavefunction - either Hartree-Fock or DFT using selected funtionals - for a fragment of the crystal. This fregment can be embedded in an electrostatic crystal field by employing cluster charges. The following options were used: SOFTWARE: ORCA PARTITIONING: NoSpherA2 INT ACCURACY: Normal METHOD: M062X BASIS SET: x2c-TZVPP CHARGE: 0 MULTIPLICITY: 1 RELATIVISTIC: DKH2 DATE: 2021-02-14_18-53-41 |
x | y | z | Uiso*/Ueq | ||
O2 | 0.31533 (7) | 0.45284 (5) | 1.01583 (3) | 0.00805 (8) | |
O1 | 0.74155 (7) | 0.44673 (6) | 1.09914 (3) | 0.00847 (8) | |
N1 | 0.87626 (10) | 0.63462 (6) | 0.87300 (4) | 0.00670 (9) | |
H1A | 0.9395 (16) | 0.6386 (12) | 0.7759 (8) | 0.0180 (19) | |
H1B | 1.0107 (16) | 0.5691 (12) | 0.9411 (8) | 0.016 (2) | |
H1C | 0.8493 (17) | 0.7655 (12) | 0.9094 (9) | 0.019 (2) | |
N3 | 0.72055 (9) | 0.44327 (7) | 0.38766 (4) | 0.00739 (9) | |
H3 | 0.6885 (14) | 0.4347 (13) | 0.2818 (7) | 0.0134 (19) | |
N2 | 0.92189 (9) | 0.51432 (6) | 0.60095 (4) | 0.00714 (10) | |
C1 | 0.55412 (11) | 0.47508 (7) | 1.00470 (5) | 0.00581 (10) | |
C4 | 0.69853 (11) | 0.41306 (7) | 0.61655 (5) | 0.00627 (11) | |
C6 | 0.57237 (11) | 0.36816 (8) | 0.48466 (5) | 0.00733 (11) | |
H6 | 0.3961 (15) | 0.2918 (12) | 0.4530 (7) | 0.022 (2) | |
C2 | 0.62067 (10) | 0.53564 (7) | 0.85771 (5) | 0.00583 (10) | |
H2 | 0.4708 (13) | 0.6313 (10) | 0.8108 (6) | 0.0117 (17) | |
C5 | 0.92631 (11) | 0.52932 (8) | 0.46208 (5) | 0.00783 (11) | |
H5 | 1.0721 (15) | 0.6038 (11) | 0.4133 (7) | 0.026 (2) | |
C3 | 0.62991 (12) | 0.36483 (7) | 0.76129 (5) | 0.00731 (11) | |
H3A | 0.7703 (15) | 0.2692 (11) | 0.8163 (8) | 0.0230 (19) | |
H3B | 0.4355 (15) | 0.3026 (11) | 0.7513 (7) | 0.0201 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.00614 (19) | 0.00906 (18) | 0.00920 (14) | −0.00018 (17) | 0.00196 (13) | 0.00264 (14) |
O1 | 0.0071 (2) | 0.01195 (18) | 0.00635 (14) | −0.00011 (18) | 0.00069 (12) | 0.00161 (14) |
N1 | 0.0071 (2) | 0.0060 (2) | 0.00698 (18) | −0.00118 (19) | 0.00082 (17) | −0.00020 (16) |
H1A | 0.022 (5) | 0.021 (5) | 0.012 (2) | 0.006 (3) | 0.0058 (14) | 0.0043 (16) |
H1B | 0.015 (4) | 0.016 (4) | 0.015 (3) | 0.001 (2) | −0.0047 (18) | 0.0038 (18) |
H1C | 0.022 (5) | 0.012 (3) | 0.023 (4) | 0.0021 (17) | 0.005 (3) | −0.0029 (15) |
N3 | 0.0087 (2) | 0.0079 (2) | 0.00553 (16) | −0.00014 (19) | 0.00092 (14) | −0.00005 (16) |
H3 | 0.016 (4) | 0.015 (5) | 0.009 (2) | −0.002 (3) | 0.0011 (12) | −0.0015 (13) |
N2 | 0.0070 (2) | 0.0078 (2) | 0.00656 (17) | −0.00197 (18) | 0.00065 (15) | −0.00049 (15) |
C1 | 0.0063 (3) | 0.0053 (3) | 0.00605 (18) | 0.0003 (2) | 0.00129 (17) | 0.00000 (17) |
C4 | 0.0073 (3) | 0.0064 (3) | 0.00533 (19) | −0.0005 (2) | 0.00162 (17) | 0.00000 (16) |
C6 | 0.0079 (3) | 0.0076 (3) | 0.0063 (2) | −0.0012 (2) | 0.00037 (18) | −0.00089 (18) |
H6 | 0.017 (3) | 0.027 (5) | 0.021 (4) | −0.0114 (19) | −0.0002 (19) | −0.001 (3) |
C2 | 0.0060 (3) | 0.0064 (2) | 0.00523 (19) | 0.0002 (2) | 0.00109 (17) | 0.00051 (18) |
H2 | 0.010 (4) | 0.002 (3) | 0.022 (4) | −0.0009 (17) | −0.002 (2) | 0.004 (2) |
C5 | 0.0082 (3) | 0.0081 (2) | 0.0075 (2) | −0.0008 (2) | 0.00207 (18) | 0.00025 (18) |
H5 | 0.028 (4) | 0.034 (6) | 0.018 (4) | −0.016 (2) | 0.0074 (18) | 0.004 (2) |
C3 | 0.0096 (3) | 0.0061 (2) | 0.0064 (2) | −0.0014 (2) | 0.00139 (18) | −0.00036 (17) |
H3A | 0.028 (4) | 0.014 (4) | 0.025 (4) | 0.0066 (18) | −0.005 (2) | 0.001 (2) |
H3B | 0.016 (3) | 0.020 (4) | 0.024 (4) | −0.0069 (15) | 0.0021 (17) | −0.002 (3) |
O2—C1 | 1.2611 (6) | N2—C5 | 1.3261 (6) |
O1—C1 | 1.2530 (6) | C1—C2 | 1.5415 (7) |
N1—H1A | 1.016 (7) | C4—C6 | 1.3776 (6) |
N1—H1B | 1.007 (8) | C4—C3 | 1.5020 (7) |
N1—H1C | 1.023 (9) | C6—H6 | 1.076 (7) |
N1—C2 | 1.4930 (7) | C2—H2 | 1.091 (7) |
N3—H3 | 1.000 (6) | C2—C3 | 1.5419 (7) |
N3—C6 | 1.3794 (7) | C5—H5 | 1.076 (7) |
N3—C5 | 1.3533 (7) | C3—H3A | 1.088 (7) |
N2—C4 | 1.3897 (7) | C3—H3B | 1.094 (8) |
H1B—N1—H1A | 108.8 (6) | H6—C6—N3 | 122.4 (4) |
H1C—N1—H1A | 110.6 (7) | H6—C6—C4 | 131.6 (4) |
H1C—N1—H1B | 109.3 (6) | C1—C2—N1 | 109.95 (4) |
C2—N1—H1A | 107.7 (5) | H2—C2—N1 | 108.1 (4) |
C2—N1—H1B | 111.6 (5) | H2—C2—C1 | 108.9 (4) |
C2—N1—H1C | 108.7 (5) | C3—C2—N1 | 110.51 (4) |
C6—N3—H3 | 127.6 (4) | C3—C2—C1 | 109.67 (4) |
C5—N3—H3 | 125.1 (4) | C3—C2—H2 | 109.7 (3) |
C5—N3—C6 | 107.28 (4) | N2—C5—N3 | 111.91 (5) |
C5—N2—C4 | 105.37 (4) | H5—C5—N3 | 123.5 (4) |
O1—C1—O2 | 126.63 (5) | H5—C5—N2 | 124.6 (4) |
C2—C1—O2 | 116.20 (4) | C2—C3—C4 | 112.66 (4) |
C2—C1—O1 | 117.12 (5) | H3A—C3—C4 | 111.6 (4) |
C6—C4—N2 | 109.48 (4) | H3A—C3—C2 | 107.0 (4) |
C3—C4—N2 | 120.82 (4) | H3B—C3—C4 | 109.5 (4) |
C3—C4—C6 | 129.69 (5) | H3B—C3—C2 | 106.6 (4) |
C4—C6—N3 | 105.96 (5) | H3B—C3—H3A | 109.3 (6) |
C5—N2—C4—C3 | 178.91 (5) | O1—C1—C2—N1 | −27.41 (6) |
C6—N3—C5—N2 | 0.25 (7) | O2—C1—C2—C3 | −83.27 (6) |
O1—C1—C2—C3 | 94.30 (6) | C2—C3—C4—N2 | 53.66 (7) |
N1—C2—C3—C4 | −57.64 (6) | C3—C4—C6—N3 | −178.61 (5) |
C2—C3—C4—C6 | −127.97 (6) | H1A—N1—C2—H2 | −77.8 (6) |
H1A—N1—C2—C1 | 163.5 (5) | H1B—N1—C2—H2 | 162.8 (6) |
H1B—N1—C2—C1 | 44.1 (5) | H1C—N1—C2—H2 | 42.2 (6) |
H1C—N1—C2—C1 | −76.5 (5) | H3—N3—C5—N2 | −178.3 (6) |
C4—N2—C5—H5 | 178.1 (5) | H3—N3—C6—C4 | 178.4 (6) |
H3—N3—C5—H5 | 3.3 (8) | O2—C1—C2—H2 | 36.8 (4) |
H3—N3—C6—H6 | −1.6 (8) | N1—C2—C3—H3A | 65.4 (4) |
C5—N2—C4—C6 | 0.24 (6) | C1—C2—C3—H3B | 60.9 (4) |
C5—N3—C6—C4 | −0.09 (7) | H2—C2—C3—H3B | −58.7 (5) |
O2—C1—C2—N1 | 155.03 (4) | H3B—C3—C4—N2 | 172.1 (4) |
C1—C2—C3—C4 | −179.00 (5) | C3—C4—C6—H6 | 1.4 (6) |
N2—C4—C6—N3 | −0.09 (6) | N1—C2—C3—H3B | −177.8 (4) |
H1A—N1—C2—C3 | 42.3 (5) | H2—C2—C3—C4 | 61.4 (4) |
H1B—N1—C2—C3 | −77.1 (5) | H3A—C3—C4—N2 | −66.7 (4) |
H1C—N1—C2—C3 | 162.3 (5) | H3B—C3—C4—C6 | −9.5 (4) |
C6—N3—C5—H5 | −178.2 (5) | C1—C2—C3—H3A | −56.0 (4) |
C5—N3—C6—H6 | 179.9 (5) | H2—C2—C3—H3A | −175.6 (6) |
O1—C1—C2—H2 | −145.6 (4) | H3A—C3—C4—C6 | 111.7 (5) |
C4—N2—C5—N3 | −0.31 (6) | N2—C4—C6—H6 | 179.9 (6) |
C6H9N3O2 | F(000) = 164.036 |
Mr = 155.16 | Dx = 1.455 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.1656 (2) Å | Cell parameters from 2706 reflections |
b = 7.2761 (3) Å | θ = 3.5–30.4° |
c = 9.4978 (3) Å | µ = 0.11 mm−1 |
β = 97.316 (3)° | T = 105 K |
V = 354.07 (2) Å3 | Plate, colourless |
Z = 2 | 0.2 × 0.2 × 0.1 mm |
Bruker APEX-II CCD diffractometer | 2148 independent reflections |
Radiation source: rotating anode, Bruker TXS with Helios Optics | 2032 reflections with I ≥ 2u(I) |
Multilayer optics monochromator | Rint = 0.033 |
φ scans | θmax = 30.5°, θmin = 3.5° |
Absorption correction: multi-scan SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 | h = −7→7 |
Tmin = 0.650, Tmax = 0.746 | k = −10→10 |
11193 measured reflections | l = −13→13 |
Refinement on F2 | 0 constraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.022 | w = 1/[σ2(Fo2) + (0.0076P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.032 | (Δ/σ)max = 0.0001 |
S = 1.18 | Δρmax = 0.15 e Å−3 |
2148 reflections | Δρmin = −0.12 e Å−3 |
181 parameters | Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881. |
100 restraints | Absolute structure parameter: 0.3 (11) |
Refinement. Refinement using NoSpherA2, an implementation of NOn-SPHERical Atom-form-factors in Olex2. Please cite: F. Kleemiss et al. DOI 10.1039/D0SC05526C - 2020 NoSpherA2 implementation of HAR makes use of tailor-made aspherical atomic form factors calculated on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from spherical-atom form factors. The ED is calculated from a gaussian basis set single determinant SCF wavefunction - either Hartree-Fock or DFT using selected funtionals - for a fragment of the crystal. This fregment can be embedded in an electrostatic crystal field by employing cluster charges. The following options were used: SOFTWARE: ORCA PARTITIONING: NoSpherA2 INT ACCURACY: Normal METHOD: M062X BASIS SET: x2c-TZVPP CHARGE: 0 MULTIPLICITY: 1 RELATIVISTIC: DKH2 DATE: 2021-02-14_21-31-35 |
x | y | z | Uiso*/Ueq | ||
O2 | 0.31462 (8) | 0.45104 (7) | 1.01449 (4) | 0.01453 (10) | |
O1 | 0.73996 (8) | 0.44614 (8) | 1.09888 (4) | 0.01520 (11) | |
N1 | 0.87419 (11) | 0.63417 (8) | 0.87357 (6) | 0.01094 (12) | |
H1A | 0.9415 (19) | 0.6410 (15) | 0.7770 (10) | 0.027 (3) | |
H1B | 1.0108 (19) | 0.5709 (14) | 0.9431 (9) | 0.023 (2) | |
H1C | 0.8448 (18) | 0.7607 (15) | 0.9100 (10) | 0.022 (2) | |
N3 | 0.72092 (10) | 0.44401 (10) | 0.38769 (5) | 0.01304 (12) | |
H3 | 0.6849 (15) | 0.4344 (15) | 0.2827 (8) | 0.021 (2) | |
N2 | 0.92139 (11) | 0.51550 (8) | 0.60132 (5) | 0.01285 (13) | |
C1 | 0.55305 (12) | 0.47409 (9) | 1.00405 (6) | 0.00975 (14) | |
C4 | 0.69926 (12) | 0.41379 (9) | 0.61629 (6) | 0.01066 (15) | |
C6 | 0.57349 (13) | 0.36888 (10) | 0.48424 (6) | 0.01262 (14) | |
H6 | 0.3984 (17) | 0.2938 (14) | 0.4523 (8) | 0.032 (3) | |
C2 | 0.61967 (12) | 0.53500 (10) | 0.85723 (6) | 0.00947 (13) | |
H2 | 0.4685 (14) | 0.6303 (12) | 0.8112 (7) | 0.019 (2) | |
C5 | 0.92565 (13) | 0.53046 (10) | 0.46240 (6) | 0.01370 (14) | |
H5 | 1.0726 (17) | 0.6058 (13) | 0.4133 (8) | 0.035 (3) | |
C3 | 0.63061 (14) | 0.36558 (10) | 0.76089 (6) | 0.01275 (14) | |
H3A | 0.7714 (17) | 0.2688 (12) | 0.8157 (9) | 0.027 (2) | |
H3B | 0.4403 (17) | 0.3002 (13) | 0.7510 (9) | 0.030 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0113 (2) | 0.0168 (3) | 0.01614 (19) | 0.0001 (2) | 0.00433 (16) | 0.0054 (2) |
O1 | 0.0128 (2) | 0.0240 (3) | 0.00897 (17) | −0.0002 (2) | 0.00203 (16) | 0.0036 (2) |
N1 | 0.0123 (3) | 0.0110 (4) | 0.0096 (2) | −0.0018 (3) | 0.0015 (2) | −0.0007 (2) |
H1A | 0.037 (6) | 0.025 (6) | 0.021 (3) | 0.010 (4) | 0.0118 (19) | 0.007 (2) |
H1B | 0.017 (5) | 0.021 (6) | 0.028 (4) | −0.002 (3) | −0.007 (2) | 0.008 (2) |
H1C | 0.025 (6) | 0.014 (4) | 0.026 (5) | 0.000 (2) | 0.005 (3) | −0.004 (2) |
N3 | 0.0166 (3) | 0.0145 (3) | 0.0082 (2) | 0.0005 (3) | 0.00208 (18) | −0.0005 (2) |
H3 | 0.026 (5) | 0.028 (6) | 0.009 (3) | −0.002 (4) | 0.0024 (16) | 0.0003 (17) |
N2 | 0.0140 (3) | 0.0145 (3) | 0.0101 (2) | −0.0036 (2) | 0.00176 (19) | −0.0010 (2) |
C1 | 0.0108 (3) | 0.0097 (4) | 0.0091 (2) | 0.0004 (3) | 0.0030 (2) | 0.0003 (2) |
C4 | 0.0139 (3) | 0.0101 (4) | 0.0083 (2) | −0.0012 (3) | 0.0028 (2) | −0.0002 (2) |
C6 | 0.0144 (3) | 0.0135 (4) | 0.0099 (3) | −0.0014 (3) | 0.0012 (2) | −0.0015 (2) |
H6 | 0.026 (4) | 0.043 (6) | 0.027 (5) | −0.017 (3) | −0.002 (2) | −0.004 (3) |
C2 | 0.0102 (3) | 0.0108 (4) | 0.0077 (2) | 0.0000 (3) | 0.0022 (2) | 0.0008 (2) |
H2 | 0.019 (4) | 0.008 (4) | 0.028 (5) | 0.005 (2) | −0.005 (3) | 0.007 (3) |
C5 | 0.0155 (3) | 0.0155 (4) | 0.0108 (3) | −0.0008 (3) | 0.0043 (2) | 0.0010 (3) |
H5 | 0.038 (5) | 0.043 (7) | 0.028 (5) | −0.016 (3) | 0.014 (2) | 0.005 (3) |
C3 | 0.0186 (4) | 0.0103 (4) | 0.0099 (3) | −0.0034 (3) | 0.0038 (2) | −0.0003 (2) |
H3A | 0.042 (5) | 0.019 (5) | 0.019 (5) | 0.008 (2) | −0.002 (3) | −0.002 (3) |
H3B | 0.027 (4) | 0.031 (5) | 0.032 (5) | −0.014 (2) | 0.007 (2) | −0.003 (3) |
O2—C1 | 1.2594 (7) | N2—C5 | 1.3270 (7) |
O1—C1 | 1.2503 (7) | C1—C2 | 1.5432 (8) |
N1—H1A | 1.022 (9) | C4—C6 | 1.3763 (8) |
N1—H1B | 1.014 (9) | C4—C3 | 1.5030 (8) |
N1—H1C | 1.002 (11) | C6—H6 | 1.067 (8) |
N1—C2 | 1.4904 (8) | C2—H2 | 1.093 (8) |
N3—H3 | 0.994 (7) | C2—C3 | 1.5405 (9) |
N3—C6 | 1.3775 (8) | C5—H5 | 1.089 (8) |
N3—C5 | 1.3515 (9) | C3—H3A | 1.095 (8) |
N2—C4 | 1.3878 (8) | C3—H3B | 1.085 (9) |
H1B—N1—H1A | 108.5 (8) | H6—C6—N3 | 122.3 (5) |
H1C—N1—H1A | 110.4 (8) | H6—C6—C4 | 131.7 (5) |
H1C—N1—H1B | 108.4 (7) | C1—C2—N1 | 109.89 (5) |
C2—N1—H1A | 109.1 (6) | H2—C2—N1 | 108.1 (5) |
C2—N1—H1B | 112.3 (6) | H2—C2—C1 | 108.3 (4) |
C2—N1—H1C | 108.1 (5) | C3—C2—N1 | 110.53 (5) |
C6—N3—H3 | 126.3 (5) | C3—C2—C1 | 109.64 (6) |
C5—N3—H3 | 126.4 (5) | C3—C2—H2 | 110.4 (4) |
C5—N3—C6 | 107.29 (5) | N2—C5—N3 | 111.89 (6) |
C5—N2—C4 | 105.32 (5) | H5—C5—N3 | 123.5 (4) |
O1—C1—O2 | 126.50 (5) | H5—C5—N2 | 124.6 (4) |
C2—C1—O2 | 116.25 (5) | C2—C3—C4 | 112.75 (6) |
C2—C1—O1 | 117.20 (5) | H3A—C3—C4 | 111.4 (5) |
C6—C4—N2 | 109.50 (5) | H3A—C3—C2 | 107.7 (4) |
C3—C4—N2 | 120.82 (5) | H3B—C3—C4 | 109.8 (4) |
C3—C4—C6 | 129.67 (6) | H3B—C3—C2 | 107.5 (5) |
C4—C6—N3 | 105.99 (6) | H3B—C3—H3A | 107.4 (7) |
C5—N2—C4—C3 | 179.01 (6) | O1—C1—C2—N1 | −27.52 (8) |
C6—N3—C5—N2 | 0.32 (8) | O2—C1—C2—C3 | −83.32 (7) |
O1—C1—C2—C3 | 94.16 (7) | C2—C3—C4—N2 | 53.53 (8) |
N1—C2—C3—C4 | −57.73 (7) | C3—C4—C6—N3 | −178.69 (7) |
C2—C3—C4—C6 | −127.85 (7) | H1A—N1—C2—H2 | −78.2 (7) |
H1A—N1—C2—C1 | 163.8 (6) | H1B—N1—C2—H2 | 161.4 (7) |
H1B—N1—C2—C1 | 43.5 (6) | H1C—N1—C2—H2 | 41.9 (7) |
H1C—N1—C2—C1 | −76.1 (6) | H3—N3—C5—N2 | −178.7 (7) |
C4—N2—C5—H5 | 178.3 (6) | H3—N3—C6—C4 | 178.8 (7) |
H3—N3—C5—H5 | 2.7 (9) | O2—C1—C2—H2 | 37.2 (5) |
H3—N3—C6—H6 | −1.6 (10) | N1—C2—C3—H3A | 65.6 (5) |
C5—N2—C4—C6 | 0.14 (8) | C1—C2—C3—H3B | 59.8 (5) |
C5—N3—C6—C4 | −0.22 (8) | H2—C2—C3—H3B | −59.5 (6) |
O2—C1—C2—N1 | 155.01 (6) | H3B—C3—C4—N2 | 173.4 (5) |
C1—C2—C3—C4 | −179.02 (5) | C3—C4—C6—H6 | 1.8 (7) |
N2—C4—C6—N3 | 0.06 (7) | N1—C2—C3—H3B | −179.0 (5) |
H1A—N1—C2—C3 | 42.7 (6) | H2—C2—C3—C4 | 61.8 (4) |
H1B—N1—C2—C3 | −77.7 (6) | H3A—C3—C4—N2 | −67.7 (5) |
H1C—N1—C2—C3 | 162.8 (6) | H3B—C3—C4—C6 | −8.0 (5) |
C6—N3—C5—H5 | −178.3 (6) | C1—C2—C3—H3A | −55.7 (5) |
C5—N3—C6—H6 | 179.4 (6) | H2—C2—C3—H3A | −174.9 (6) |
O1—C1—C2—H2 | −145.4 (4) | H3A—C3—C4—C6 | 110.9 (5) |
C4—N2—C5—N3 | −0.28 (8) | N2—C4—C6—H6 | −179.5 (7) |
C6H9N3O2 | F(000) = 164.037 |
Mr = 155.16 | Dx = 1.428 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.1854 (8) Å | Cell parameters from 2412 reflections |
b = 7.3998 (10) Å | θ = 3.5–30.2° |
c = 9.4976 (12) Å | µ = 0.11 mm−1 |
β = 98.182 (10)° | T = 295 K |
V = 360.72 (9) Å3 | Plate, colourless |
Z = 2 | 0.2 × 0.2 × 0.1 mm |
Bruker APEX-II CCD diffractometer | 1806 independent reflections |
Radiation source: rotating anode, Bruker TXS with Helios Optics | 1683 reflections with I ≥ 2u(I) |
Multilayer optics monochromator | Rint = 0.024 |
φ scans | θmax = 30.6°, θmin = 3.5° |
Absorption correction: multi-scan SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 | h = −6→5 |
Tmin = 0.689, Tmax = 0.746 | k = −10→10 |
11356 measured reflections | l = −13→13 |
Refinement on F2 | 0 constraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.025 | w = 1/[σ2(Fo2) + (0.0158P)2 + 0.0067P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.049 | (Δ/σ)max = 0.001 |
S = 1.35 | Δρmax = 0.10 e Å−3 |
1806 reflections | Δρmin = −0.10 e Å−3 |
181 parameters | Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881. |
1 restraint | Absolute structure parameter: 1.0 (15) |
Refinement. Refinement using NoSpherA2, an implementation of NOn-SPHERical Atom-form-factors in Olex2. Please cite: F. Kleemiss et al. DOI 10.1039/D0SC05526C - 2020 NoSpherA2 implementation of HAR makes use of tailor-made aspherical atomic form factors calculated on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from spherical-atom form factors. The ED is calculated from a gaussian basis set single determinant SCF wavefunction - either Hartree-Fock or DFT using selected funtionals - for a fragment of the crystal. This fragment can be embedded in an electrostatic crystal field by employing cluster charges. The following options were used: SOFTWARE: ORCA PARTITIONING: NoSpherA2 INT ACCURACY: Normal METHOD: M062X BASIS SET: x2c-TZVPP CHARGE: 0 MULTIPLICITY: 1 RELATIVISTIC: DKH2 DATE: 2021-02-15_01-00-11 |
x | y | z | Uiso*/Ueq | ||
O2 | 0.31397 (17) | 0.44525 (12) | 1.01027 (8) | 0.0366 (2) | |
O1 | 0.73608 (15) | 0.44348 (13) | 1.09800 (7) | 0.0393 (2) | |
N1 | 0.8687 (2) | 0.63339 (13) | 0.87608 (10) | 0.0249 (2) | |
H1A | 0.934 (3) | 0.642 (2) | 0.7802 (17) | 0.041 (4) | |
H1B | 0.997 (3) | 0.568 (2) | 0.9444 (18) | 0.047 (5) | |
H1C | 0.837 (3) | 0.755 (2) | 0.9137 (17) | 0.043 (5) | |
N3 | 0.72208 (19) | 0.44672 (15) | 0.38771 (8) | 0.0321 (2) | |
H3 | 0.690 (3) | 0.429 (3) | 0.2813 (15) | 0.052 (5) | |
N2 | 0.9189 (2) | 0.51988 (13) | 0.60207 (8) | 0.0317 (2) | |
C1 | 0.5502 (2) | 0.47060 (14) | 1.00185 (9) | 0.0237 (2) | |
C4 | 0.7011 (2) | 0.41693 (13) | 0.61567 (9) | 0.0257 (3) | |
C6 | 0.5775 (3) | 0.37123 (15) | 0.48334 (10) | 0.0314 (3) | |
H6 | 0.406 (3) | 0.292 (3) | 0.4481 (15) | 0.065 (5) | |
C2 | 0.6172 (2) | 0.53295 (14) | 0.85629 (9) | 0.0215 (2) | |
H2 | 0.465 (2) | 0.6270 (19) | 0.8093 (12) | 0.032 (4) | |
C5 | 0.9232 (3) | 0.53403 (17) | 0.46361 (10) | 0.0338 (3) | |
H5 | 1.071 (4) | 0.608 (3) | 0.4137 (14) | 0.066 (5) | |
C3 | 0.6341 (3) | 0.36806 (14) | 0.75968 (10) | 0.0298 (3) | |
H3A | 0.774 (4) | 0.275 (2) | 0.8164 (17) | 0.069 (6) | |
H3B | 0.447 (4) | 0.298 (3) | 0.7443 (17) | 0.075 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0264 (5) | 0.0449 (5) | 0.0406 (4) | 0.0005 (4) | 0.0121 (3) | 0.0173 (4) |
O1 | 0.0312 (5) | 0.0676 (5) | 0.0193 (3) | 0.0019 (5) | 0.0046 (3) | 0.0101 (4) |
N1 | 0.0284 (6) | 0.0258 (5) | 0.0208 (4) | −0.0035 (4) | 0.0045 (4) | −0.0011 (4) |
H1A | 0.040 (13) | 0.053 (12) | 0.034 (9) | −0.006 (9) | 0.016 (8) | 0.011 (9) |
H1B | 0.031 (12) | 0.045 (11) | 0.060 (11) | −0.007 (9) | −0.017 (9) | 0.014 (9) |
H1C | 0.054 (13) | 0.031 (10) | 0.048 (11) | 0.021 (9) | 0.017 (9) | −0.009 (8) |
N3 | 0.0415 (6) | 0.0374 (5) | 0.0179 (3) | 0.0017 (5) | 0.0061 (3) | 0.0004 (4) |
H3 | 0.094 (14) | 0.046 (11) | 0.017 (7) | 0.015 (12) | 0.008 (8) | 0.013 (8) |
N2 | 0.0340 (6) | 0.0397 (5) | 0.0222 (4) | −0.0090 (4) | 0.0063 (4) | −0.0016 (4) |
C1 | 0.0257 (7) | 0.0271 (5) | 0.0192 (4) | 0.0027 (4) | 0.0069 (4) | 0.0027 (3) |
C4 | 0.0348 (7) | 0.0253 (5) | 0.0178 (4) | −0.0035 (4) | 0.0067 (4) | −0.0015 (3) |
C6 | 0.0399 (9) | 0.0337 (6) | 0.0205 (4) | −0.0049 (5) | 0.0040 (5) | −0.0044 (4) |
H6 | 0.073 (13) | 0.080 (13) | 0.037 (10) | −0.032 (11) | −0.011 (8) | −0.008 (9) |
C2 | 0.0233 (6) | 0.0246 (4) | 0.0169 (4) | −0.0001 (4) | 0.0043 (4) | 0.0026 (3) |
H2 | 0.024 (8) | 0.028 (8) | 0.043 (8) | 0.006 (6) | −0.002 (6) | 0.024 (7) |
C5 | 0.0388 (9) | 0.0416 (6) | 0.0235 (5) | −0.0042 (6) | 0.0129 (5) | 0.0023 (4) |
H5 | 0.078 (14) | 0.090 (16) | 0.036 (9) | −0.008 (12) | 0.028 (8) | −0.006 (10) |
C3 | 0.0463 (9) | 0.0243 (5) | 0.0200 (4) | −0.0084 (5) | 0.0088 (4) | −0.0014 (4) |
H3A | 0.127 (19) | 0.041 (11) | 0.041 (10) | 0.026 (12) | 0.020 (11) | 0.015 (8) |
H3B | 0.080 (16) | 0.098 (15) | 0.048 (11) | −0.066 (13) | 0.015 (9) | −0.011 (11) |
O2—C1 | 1.2529 (14) | N2—C5 | 1.3224 (13) |
O1—C1 | 1.2461 (12) | C1—C2 | 1.5433 (13) |
N1—H1A | 1.018 (16) | C4—C6 | 1.3695 (13) |
N1—H1B | 0.988 (16) | C4—C3 | 1.5026 (13) |
N1—H1C | 0.988 (16) | C6—H6 | 1.076 (16) |
N1—C2 | 1.4896 (14) | C2—H2 | 1.098 (12) |
N3—H3 | 1.010 (14) | C2—C3 | 1.5366 (14) |
N3—C6 | 1.3759 (15) | C5—H5 | 1.103 (18) |
N3—C5 | 1.3455 (16) | C3—H3A | 1.089 (17) |
N2—C4 | 1.3833 (14) | C3—H3B | 1.090 (17) |
H1B—N1—H1A | 110.0 (14) | H6—C6—N3 | 121.2 (8) |
H1C—N1—H1A | 110.9 (14) | H6—C6—C4 | 132.7 (8) |
H1C—N1—H1B | 109.8 (13) | C1—C2—N1 | 109.93 (8) |
C2—N1—H1A | 108.4 (9) | H2—C2—N1 | 107.5 (7) |
C2—N1—H1B | 109.5 (10) | H2—C2—C1 | 108.3 (7) |
C2—N1—H1C | 108.1 (10) | C3—C2—N1 | 110.38 (9) |
C6—N3—H3 | 125.5 (11) | C3—C2—C1 | 109.68 (8) |
C5—N3—H3 | 127.1 (11) | C3—C2—H2 | 111.0 (7) |
C5—N3—C6 | 107.15 (9) | N2—C5—N3 | 111.92 (11) |
C5—N2—C4 | 105.42 (9) | H5—C5—N3 | 122.8 (8) |
O1—C1—O2 | 126.19 (10) | H5—C5—N2 | 125.3 (8) |
C2—C1—O2 | 116.66 (8) | C2—C3—C4 | 113.12 (8) |
C2—C1—O1 | 117.08 (11) | H3A—C3—C4 | 112.2 (10) |
C6—C4—N2 | 109.39 (9) | H3A—C3—C2 | 107.4 (9) |
C3—C4—N2 | 121.02 (9) | H3B—C3—C4 | 108.0 (8) |
C3—C4—C6 | 129.58 (11) | H3B—C3—C2 | 109.3 (11) |
C4—C6—N3 | 106.12 (11) | H3B—C3—H3A | 106.5 (17) |
C5—N2—C4—C3 | 178.65 (10) | O1—C1—C2—N1 | −27.95 (13) |
C6—N3—C5—N2 | 0.12 (15) | O2—C1—C2—C3 | −83.69 (12) |
O1—C1—C2—C3 | 93.59 (12) | C2—C3—C4—N2 | 53.66 (15) |
N1—C2—C3—C4 | −58.25 (13) | C3—C4—C6—N3 | −178.44 (11) |
C2—C3—C4—C6 | −127.85 (13) | H1A—N1—C2—H2 | −78.1 (11) |
H1A—N1—C2—C1 | 164.3 (9) | H1B—N1—C2—H2 | 162.1 (12) |
H1B—N1—C2—C1 | 44.4 (10) | H1C—N1—C2—H2 | 42.4 (12) |
H1C—N1—C2—C1 | −75.2 (10) | H3—N3—C5—N2 | −174.7 (15) |
C4—N2—C5—H5 | 179.8 (14) | H3—N3—C6—C4 | 174.7 (14) |
H3—N3—C5—H5 | 6 (2) | O2—C1—C2—H2 | 37.6 (7) |
H3—N3—C6—H6 | −4.2 (19) | N1—C2—C3—H3A | 66.2 (11) |
C5—N2—C4—C6 | −0.12 (13) | C1—C2—C3—H3B | 60.1 (10) |
C5—N3—C6—C4 | −0.19 (14) | H2—C2—C3—H3B | −59.5 (12) |
O2—C1—C2—N1 | 154.78 (9) | H3B—C3—C4—N2 | 174.9 (12) |
C1—C2—C3—C4 | −179.51 (10) | C3—C4—C6—H6 | 0.3 (15) |
N2—C4—C6—N3 | 0.19 (13) | N1—C2—C3—H3B | −178.7 (10) |
H1A—N1—C2—C3 | 43.2 (9) | H2—C2—C3—C4 | 60.9 (7) |
H1B—N1—C2—C3 | −76.7 (10) | H3A—C3—C4—N2 | −68.0 (10) |
H1C—N1—C2—C3 | 163.7 (10) | H3B—C3—C4—C6 | −6.6 (12) |
C6—N3—C5—H5 | −179.7 (13) | C1—C2—C3—H3A | −55.1 (11) |
C5—N3—C6—H6 | −179.1 (13) | H2—C2—C3—H3A | −174.7 (12) |
O1—C1—C2—H2 | −145.1 (7) | H3A—C3—C4—C6 | 110.5 (10) |
C4—N2—C5—N3 | 0.00 (14) | N2—C4—C6—H6 | 179.0 (15) |
C6H9N3O2 | Dx = 1.477 Mg m−3 |
Mr = 155.16 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 7499 reflections |
a = 5.1498 (2) Å | θ = 3.0–36.3° |
b = 7.1902 (2) Å | µ = 0.11 mm−1 |
c = 18.8503 (6) Å | T = 5 K |
V = 697.99 (4) Å3 | Needle, colourless |
Z = 4 | 0.2 × 0.1 × 0.1 mm |
F(000) = 328.072 |
Bruker APEX-II CCD diffractometer | 2928 independent reflections |
Radiation source: rotating anode, Bruker TXS with Helios Optics | 2768 reflections with I ≥ 2u(I) |
Multilayer optics monochromator | Rint = 0.027 |
φ scans | θmax = 36.3°, θmin = 3.0° |
Absorption correction: multi-scan SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 | h = −8→8 |
Tmin = 0.682, Tmax = 0.747 | k = −10→10 |
13716 measured reflections | l = −28→28 |
Refinement on F2 | 0 constraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.019 | w = 1/[σ2(Fo2) + (0.010P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.032 | (Δ/σ)max = 0.0001 |
S = 1.13 | Δρmax = 0.17 e Å−3 |
2928 reflections | Δρmin = −0.13 e Å−3 |
181 parameters | Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881. |
99 restraints | Absolute structure parameter: 0.1 (7) |
Refinement. Refinement using NoSpherA2, an implementation of NOn-SPHERical Atom-form-factors in Olex2. Please cite: F. Kleemiss et al. DOI 10.1039/D0SC05526C - 2020 NoSpherA2 implementation of HAR makes use of tailor-made aspherical atomic form factors calculated on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from spherical-atom form factors. The ED is calculated from a gaussian basis set single determinant SCF wavefunction - either Hartree-Fock or DFT using selected funtionals - for a fragment of the crystal. This fregment can be embedded in an electrostatic crystal field by employing cluster charges. The following options were used: SOFTWARE: ORCA PARTITIONING: NoSpherA2 INT ACCURACY: Normal METHOD: M062X BASIS SET: x2c-TZVPP CHARGE: 0 MULTIPLICITY: 1 RELATIVISTIC: DKH2 DATE: 2021-01-25_20-30-15 |
x | y | z | Uiso*/Ueq | ||
O2 | 0.32523 (5) | 0.49519 (5) | 0.239747 (17) | 0.00711 (7) | |
O1 | 0.73277 (5) | 0.49178 (6) | 0.197479 (17) | 0.00746 (7) | |
N1 | 0.91743 (7) | 0.31183 (6) | 0.31202 (2) | 0.00606 (7) | |
N3 | 0.86938 (6) | 0.50331 (6) | 0.55327 (2) | 0.00651 (7) | |
N2 | 1.03202 (6) | 0.43924 (6) | 0.44704 (2) | 0.00638 (7) | |
C4 | 0.80291 (7) | 0.53935 (6) | 0.43875 (2) | 0.00539 (8) | |
C1 | 0.56621 (7) | 0.47000 (7) | 0.24536 (2) | 0.00510 (8) | |
C2 | 0.66640 (7) | 0.41387 (7) | 0.31927 (2) | 0.00504 (8) | |
C6 | 0.70071 (8) | 0.57917 (7) | 0.50444 (2) | 0.00626 (8) | |
C5 | 1.06292 (8) | 0.42054 (7) | 0.51647 (2) | 0.00661 (8) | |
C3 | 0.70255 (8) | 0.58731 (7) | 0.36630 (2) | 0.00640 (8) | |
H1B | 1.0360 (14) | 0.3760 (12) | 0.2769 (4) | 0.0172 (19) | |
H1C | 0.8753 (15) | 0.1814 (12) | 0.2959 (4) | 0.0205 (19) | |
H1A | 1.0081 (14) | 0.3117 (11) | 0.3601 (4) | 0.0172 (19) | |
H3 | 0.8465 (14) | 0.5059 (12) | 0.6068 (4) | 0.0173 (19) | |
H2 | 0.5256 (12) | 0.3202 (10) | 0.3429 (4) | 0.0172 (17) | |
H6 | 0.5315 (13) | 0.6553 (10) | 0.5190 (4) | 0.0217 (18) | |
H5 | 1.2182 (12) | 0.3487 (10) | 0.5412 (3) | 0.0208 (18) | |
H3A | 0.8308 (14) | 0.6852 (11) | 0.3389 (4) | 0.0203 (18) | |
H3B | 0.5223 (14) | 0.6553 (10) | 0.3706 (4) | 0.0243 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.00482 (10) | 0.00938 (18) | 0.00712 (15) | 0.00064 (13) | −0.00049 (10) | 0.00189 (12) |
O1 | 0.00583 (10) | 0.01196 (18) | 0.00459 (15) | −0.00016 (12) | 0.00017 (10) | 0.00142 (12) |
N1 | 0.00558 (13) | 0.0068 (2) | 0.00580 (19) | 0.00100 (14) | −0.00005 (13) | −0.00024 (14) |
N3 | 0.00740 (12) | 0.0082 (2) | 0.00394 (18) | 0.00061 (14) | 0.00015 (11) | 0.00013 (14) |
N2 | 0.00622 (11) | 0.0083 (2) | 0.00463 (19) | 0.00177 (12) | −0.00029 (12) | −0.00033 (13) |
C4 | 0.00607 (12) | 0.0060 (2) | 0.0041 (2) | 0.00091 (14) | −0.00079 (13) | −0.00002 (14) |
C1 | 0.00472 (13) | 0.0058 (2) | 0.0047 (2) | 0.00020 (14) | −0.00039 (14) | −0.00005 (14) |
C2 | 0.00474 (13) | 0.0061 (2) | 0.0043 (2) | 0.00002 (15) | −0.00034 (13) | 0.00045 (15) |
C6 | 0.00628 (14) | 0.0077 (2) | 0.0048 (2) | 0.00128 (15) | 0.00000 (13) | −0.00053 (15) |
C5 | 0.00626 (14) | 0.0082 (2) | 0.0054 (2) | 0.00135 (16) | −0.00092 (14) | 0.00041 (15) |
C3 | 0.00775 (14) | 0.0061 (2) | 0.0053 (2) | 0.00107 (16) | −0.00100 (14) | −0.00034 (15) |
H1B | 0.006 (3) | 0.021 (5) | 0.024 (4) | 0.009 (2) | 0.007 (2) | 0.012 (2) |
H1C | 0.027 (4) | 0.013 (3) | 0.022 (4) | −0.0043 (19) | −0.003 (3) | −0.0055 (19) |
H1A | 0.015 (4) | 0.020 (5) | 0.016 (3) | −0.003 (3) | −0.0060 (17) | 0.0018 (19) |
H3 | 0.033 (4) | 0.015 (5) | 0.004 (3) | 0.011 (4) | −0.0007 (16) | 0.0018 (17) |
H2 | 0.014 (3) | 0.011 (4) | 0.027 (4) | −0.002 (2) | −0.002 (2) | 0.007 (2) |
H6 | 0.018 (3) | 0.025 (5) | 0.022 (4) | 0.008 (2) | 0.005 (2) | 0.002 (3) |
H5 | 0.019 (3) | 0.027 (5) | 0.017 (4) | 0.008 (2) | −0.002 (2) | 0.004 (2) |
H3A | 0.023 (3) | 0.022 (4) | 0.016 (4) | −0.007 (2) | 0.000 (2) | 0.001 (2) |
H3B | 0.022 (3) | 0.021 (4) | 0.030 (5) | 0.0085 (18) | −0.002 (2) | 0.000 (3) |
O2—C1 | 1.2586 (5) | N2—C5 | 1.3252 (6) |
O1—C1 | 1.2550 (5) | C4—C6 | 1.3755 (6) |
N1—H1B | 1.012 (8) | C4—C3 | 1.5005 (6) |
N1—H1A | 1.019 (8) | C1—C2 | 1.5395 (6) |
N1—H1C | 1.010 (9) | C2—H2 | 1.085 (7) |
N1—C2 | 1.4927 (5) | C2—C3 | 1.5413 (7) |
N3—H3 | 1.017 (8) | C6—H6 | 1.065 (7) |
N3—C6 | 1.3782 (6) | C5—H5 | 1.060 (6) |
N3—C5 | 1.3524 (6) | C3—H3B | 1.052 (7) |
N2—C4 | 1.3909 (5) | C3—H3A | 1.095 (7) |
H1A—N1—H1B | 107.8 (6) | H2—C2—N1 | 108.1 (4) |
H1C—N1—H1B | 110.8 (7) | H2—C2—C1 | 108.0 (4) |
H1C—N1—H1A | 111.5 (7) | C3—C2—N1 | 110.23 (3) |
C2—N1—H1B | 111.0 (4) | C3—C2—C1 | 110.42 (4) |
C2—N1—H1A | 108.4 (4) | C3—C2—H2 | 110.3 (4) |
C2—N1—H1C | 107.3 (5) | C4—C6—N3 | 106.12 (4) |
C6—N3—H3 | 125.7 (4) | H6—C6—N3 | 123.2 (4) |
C5—N3—H3 | 127.1 (4) | H6—C6—C4 | 130.7 (4) |
C5—N3—C6 | 107.22 (4) | N2—C5—N3 | 111.93 (4) |
C5—N2—C4 | 105.39 (4) | H5—C5—N3 | 123.0 (4) |
C6—C4—N2 | 109.34 (4) | H5—C5—N2 | 125.1 (4) |
C3—C4—N2 | 120.89 (4) | C2—C3—C4 | 112.28 (4) |
C3—C4—C6 | 129.77 (4) | H3B—C3—C4 | 109.9 (4) |
O1—C1—O2 | 126.55 (4) | H3B—C3—C2 | 108.3 (4) |
C2—C1—O2 | 116.38 (4) | H3A—C3—C4 | 111.7 (4) |
C2—C1—O1 | 117.03 (3) | H3A—C3—C2 | 108.7 (4) |
C1—C2—N1 | 109.65 (4) | H3A—C3—H3B | 105.6 (6) |
C5—N2—C4—C3 | −179.69 (4) | O1—C1—C2—N1 | −26.72 (6) |
C6—N3—C5—N2 | 0.58 (5) | O2—C1—C2—C3 | −82.89 (5) |
O1—C1—C2—C3 | 94.92 (5) | C2—C3—C4—N2 | 55.80 (5) |
N1—C2—C3—C4 | −58.08 (4) | C3—C4—C6—N3 | −179.98 (7) |
C2—C3—C4—C6 | −123.97 (5) | H1A—N1—C2—H2 | −79.9 (6) |
H1A—N1—C2—C1 | 162.5 (5) | H1B—N1—C2—H2 | 161.9 (6) |
H1B—N1—C2—C1 | 44.3 (5) | H1C—N1—C2—H2 | 40.5 (6) |
H1C—N1—C2—C1 | −77.1 (5) | H3—N3—C5—N2 | 178.4 (6) |
C4—N2—C5—H5 | 179.0 (5) | H3—N3—C6—C4 | −178.4 (6) |
H3—N3—C5—H5 | −1.0 (7) | O2—C1—C2—H2 | 37.8 (4) |
H3—N3—C6—H6 | 3.3 (7) | N1—C2—C3—H3A | 66.0 (4) |
C5—N2—C4—C6 | 0.12 (5) | C1—C2—C3—H3B | 59.1 (4) |
C5—N3—C6—C4 | −0.47 (5) | H2—C2—C3—H3B | −60.3 (6) |
O2—C1—C2—N1 | 155.47 (4) | H3B—C3—C4—N2 | 176.4 (4) |
C1—C2—C3—C4 | −179.38 (3) | C3—C4—C6—H6 | −1.8 (5) |
N2—C4—C6—N3 | 0.22 (5) | N1—C2—C3—H3B | −179.6 (4) |
H1A—N1—C2—C3 | 40.7 (5) | H2—C2—C3—C4 | 61.2 (4) |
H1B—N1—C2—C3 | −77.5 (5) | H3A—C3—C4—N2 | −66.7 (4) |
H1C—N1—C2—C3 | 161.2 (5) | H3B—C3—C4—C6 | −3.4 (4) |
C6—N3—C5—H5 | −178.8 (4) | C1—C2—C3—H3A | −55.3 (4) |
C5—N3—C6—H6 | −178.8 (5) | H2—C2—C3—H3A | −174.6 (6) |
O1—C1—C2—H2 | −144.4 (4) | H3A—C3—C4—C6 | 113.6 (4) |
C4—N2—C5—N3 | −0.43 (5) | N2—C4—C6—H6 | 178.4 (5) |
C6H9N3O2 | Dx = 1.470 Mg m−3 |
Mr = 155.16 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 6123 reflections |
a = 5.1521 (1) Å | θ = 3.0–36.0° |
b = 7.2228 (2) Å | µ = 0.11 mm−1 |
c = 18.8440 (6) Å | T = 105 K |
V = 701.23 (3) Å3 | Needle, colourless |
Z = 4 | 0.2 × 0.1 × 0.1 mm |
F(000) = 328.072 |
Bruker APEX-II CCD diffractometer | 2942 independent reflections |
Radiation source: rotating anode, Bruker TXS with Helios Optics | 2706 reflections with I ≥ 2u(I) |
Multilayer optics monochromator | Rint = 0.030 |
φ scans | θmax = 36.3°, θmin = 3.0° |
Absorption correction: multi-scan SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 | h = −8→8 |
Tmin = 0.687, Tmax = 0.747 | k = −10→10 |
13793 measured reflections | l = −28→28 |
Refinement on F2 | 0 constraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.023 | w = 1/[σ2(Fo2) + (0.0119P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.038 | (Δ/σ)max = 0.0001 |
S = 1.12 | Δρmax = 0.17 e Å−3 |
2942 reflections | Δρmin = −0.15 e Å−3 |
181 parameters | Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881. |
99 restraints | Absolute structure parameter: 0.4 (8) |
Refinement. Refinement using NoSpherA2, an implementation of NOn-SPHERical Atom-form-factors in Olex2. Please cite: F. Kleemiss et al. DOI 10.1039/D0SC05526C - 2020 NoSpherA2 implementation of HAR makes use of tailor-made aspherical atomic form factors calculated on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from spherical-atom form factors. The ED is calculated from a gaussian basis set single determinant SCF wavefunction - either Hartree-Fock or DFT using selected funtionals - for a fragment of the crystal. This fregment can be embedded in an electrostatic crystal field by employing cluster charges. The following options were used: SOFTWARE: ORCA PARTITIONING: NoSpherA2 INT ACCURACY: Normal METHOD: M062X BASIS SET: x2c-TZVPP CHARGE: 0 MULTIPLICITY: 1 RELATIVISTIC: DKH2 DATE: 2021-01-23_23-40-43 |
x | y | z | Uiso*/Ueq | ||
O2 | 0.32475 (6) | 0.49818 (6) | 0.240209 (19) | 0.01318 (8) | |
O1 | 0.73091 (6) | 0.49455 (7) | 0.197629 (19) | 0.01394 (8) | |
N1 | 0.91616 (8) | 0.31391 (7) | 0.31181 (3) | 0.00998 (9) | |
H1B | 1.0343 (15) | 0.3750 (13) | 0.2770 (4) | 0.020 (2) | |
H1A | 1.0073 (14) | 0.3128 (12) | 0.3597 (5) | 0.0157 (19) | |
H1C | 0.8725 (17) | 0.1843 (14) | 0.2953 (5) | 0.023 (2) | |
N3 | 0.87041 (7) | 0.50257 (7) | 0.55335 (3) | 0.01189 (9) | |
H3 | 0.8494 (16) | 0.5062 (13) | 0.6068 (5) | 0.026 (2) | |
N2 | 1.03224 (8) | 0.43944 (7) | 0.44706 (2) | 0.01190 (9) | |
C4 | 0.80387 (9) | 0.53942 (7) | 0.43892 (3) | 0.00996 (9) | |
C1 | 0.56511 (8) | 0.47258 (8) | 0.24558 (3) | 0.00925 (9) | |
C2 | 0.66615 (8) | 0.41601 (8) | 0.31935 (3) | 0.00865 (9) | |
H2 | 0.5257 (14) | 0.3232 (11) | 0.3427 (4) | 0.0220 (19) | |
C6 | 0.70210 (9) | 0.57890 (9) | 0.50460 (3) | 0.01133 (10) | |
H6 | 0.5334 (15) | 0.6551 (11) | 0.5199 (4) | 0.028 (2) | |
C5 | 1.06326 (10) | 0.41995 (8) | 0.51647 (3) | 0.01233 (10) | |
H5 | 1.2175 (15) | 0.3476 (12) | 0.5415 (4) | 0.031 (2) | |
C3 | 0.70372 (10) | 0.58790 (9) | 0.36650 (3) | 0.01170 (10) | |
H3B | 0.5230 (16) | 0.6543 (11) | 0.3711 (4) | 0.028 (2) | |
H3A | 0.8329 (16) | 0.6849 (12) | 0.3400 (4) | 0.027 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.00938 (12) | 0.0168 (2) | 0.01336 (19) | 0.00099 (16) | −0.00125 (12) | 0.00446 (16) |
O1 | 0.01111 (13) | 0.0235 (2) | 0.00724 (18) | −0.00111 (15) | −0.00005 (12) | 0.00319 (16) |
N1 | 0.01021 (15) | 0.0109 (3) | 0.0088 (2) | 0.00160 (17) | 0.00013 (15) | −0.00024 (16) |
H1B | 0.009 (4) | 0.028 (5) | 0.022 (4) | 0.007 (2) | 0.003 (2) | 0.013 (2) |
H1A | 0.013 (4) | 0.018 (5) | 0.016 (3) | 0.000 (3) | −0.0041 (17) | 0.0022 (19) |
H1C | 0.030 (5) | 0.015 (4) | 0.025 (5) | −0.004 (2) | −0.002 (3) | −0.007 (2) |
N3 | 0.01415 (15) | 0.0143 (2) | 0.0072 (2) | −0.00054 (17) | 0.00018 (14) | −0.00025 (17) |
H3 | 0.045 (5) | 0.025 (6) | 0.007 (3) | 0.012 (4) | 0.0035 (17) | 0.0044 (17) |
N2 | 0.01215 (15) | 0.0153 (3) | 0.0083 (2) | 0.00333 (16) | −0.00046 (15) | −0.00037 (16) |
C4 | 0.01187 (15) | 0.0103 (3) | 0.0077 (2) | 0.00147 (17) | −0.00122 (16) | −0.00048 (17) |
C1 | 0.00919 (16) | 0.0107 (3) | 0.0079 (2) | −0.00063 (18) | −0.00100 (16) | 0.00048 (17) |
C2 | 0.00877 (16) | 0.0101 (3) | 0.0071 (2) | −0.00003 (18) | −0.00033 (16) | 0.00073 (17) |
H2 | 0.016 (3) | 0.014 (4) | 0.036 (5) | 0.001 (2) | 0.001 (3) | 0.008 (3) |
C6 | 0.01237 (17) | 0.0129 (3) | 0.0087 (2) | 0.00133 (19) | 0.00016 (17) | −0.00168 (18) |
H6 | 0.024 (3) | 0.031 (5) | 0.027 (5) | 0.009 (2) | 0.005 (2) | −0.003 (3) |
C5 | 0.01257 (18) | 0.0156 (3) | 0.0088 (3) | 0.0011 (2) | −0.00196 (18) | 0.00093 (19) |
H5 | 0.029 (4) | 0.040 (6) | 0.026 (4) | 0.014 (2) | −0.004 (2) | 0.003 (3) |
C3 | 0.01547 (19) | 0.0104 (3) | 0.0093 (3) | 0.0027 (2) | −0.00243 (18) | −0.00081 (19) |
H3B | 0.029 (3) | 0.023 (5) | 0.033 (5) | 0.0109 (19) | −0.005 (2) | −0.002 (3) |
H3A | 0.034 (4) | 0.022 (4) | 0.025 (4) | −0.007 (2) | 0.004 (3) | 0.001 (2) |
O2—C1 | 1.2562 (5) | N2—C5 | 1.3253 (7) |
O1—C1 | 1.2535 (6) | C4—C6 | 1.3739 (7) |
N1—H1B | 0.997 (8) | C4—C3 | 1.5005 (7) |
N1—H1A | 1.018 (8) | C1—C2 | 1.5396 (7) |
N1—H1C | 1.012 (9) | C2—H2 | 1.080 (8) |
N1—C2 | 1.4910 (6) | C2—C3 | 1.5389 (8) |
N3—H3 | 1.013 (9) | C6—H6 | 1.069 (7) |
N3—C6 | 1.3784 (7) | C5—H5 | 1.061 (7) |
N3—C5 | 1.3513 (7) | C3—H3B | 1.051 (8) |
N2—C4 | 1.3890 (6) | C3—H3A | 1.088 (8) |
H1A—N1—H1B | 107.7 (7) | H2—C2—N1 | 108.1 (4) |
H1C—N1—H1B | 110.0 (7) | H2—C2—C1 | 107.8 (4) |
H1C—N1—H1A | 111.6 (7) | C3—C2—N1 | 110.20 (4) |
C2—N1—H1B | 111.8 (5) | C3—C2—C1 | 110.47 (5) |
C2—N1—H1A | 108.5 (5) | C3—C2—H2 | 110.5 (5) |
C2—N1—H1C | 107.2 (5) | C4—C6—N3 | 106.09 (4) |
C6—N3—H3 | 125.8 (5) | H6—C6—N3 | 122.5 (5) |
C5—N3—H3 | 127.0 (5) | H6—C6—C4 | 131.4 (5) |
C5—N3—C6 | 107.25 (5) | N2—C5—N3 | 111.84 (5) |
C5—N2—C4 | 105.44 (4) | H5—C5—N3 | 122.7 (4) |
C6—C4—N2 | 109.38 (4) | H5—C5—N2 | 125.5 (4) |
C3—C4—N2 | 120.86 (4) | C2—C3—C4 | 112.34 (5) |
C3—C4—C6 | 129.76 (5) | H3B—C3—C4 | 109.6 (4) |
O1—C1—O2 | 126.52 (5) | H3B—C3—C2 | 107.7 (4) |
C2—C1—O2 | 116.43 (4) | H3A—C3—C4 | 110.9 (4) |
C2—C1—O1 | 117.00 (4) | H3A—C3—C2 | 109.4 (4) |
C1—C2—N1 | 109.71 (4) | H3A—C3—H3B | 106.6 (6) |
C5—N2—C4—C3 | −179.64 (5) | O1—C1—C2—N1 | −26.91 (7) |
C6—N3—C5—N2 | 0.65 (7) | O2—C1—C2—C3 | −82.89 (6) |
O1—C1—C2—C3 | 94.78 (6) | C2—C3—C4—N2 | 55.98 (6) |
N1—C2—C3—C4 | −58.22 (6) | C3—C4—C6—N3 | −180.00 (7) |
C2—C3—C4—C6 | −123.88 (6) | H1A—N1—C2—H2 | −80.0 (7) |
H1A—N1—C2—C1 | 162.6 (5) | H1B—N1—C2—H2 | 161.2 (7) |
H1B—N1—C2—C1 | 43.9 (5) | H1C—N1—C2—H2 | 40.6 (7) |
H1C—N1—C2—C1 | −76.7 (6) | H3—N3—C5—N2 | 179.4 (6) |
C4—N2—C5—H5 | 178.7 (6) | H3—N3—C6—C4 | −179.3 (6) |
H3—N3—C5—H5 | 0.1 (8) | O2—C1—C2—H2 | 37.9 (4) |
H3—N3—C6—H6 | 2.4 (8) | N1—C2—C3—H3A | 65.4 (5) |
C5—N2—C4—C6 | 0.25 (6) | C1—C2—C3—H3B | 59.5 (4) |
C5—N3—C6—C4 | −0.46 (6) | H2—C2—C3—H3B | −59.7 (6) |
O2—C1—C2—N1 | 155.42 (5) | H3B—C3—C4—N2 | 175.7 (5) |
C1—C2—C3—C4 | −179.63 (4) | C3—C4—C6—H6 | −1.8 (6) |
N2—C4—C6—N3 | 0.13 (6) | N1—C2—C3—H3B | −179.1 (4) |
H1A—N1—C2—C3 | 40.8 (5) | H2—C2—C3—C4 | 61.2 (4) |
H1B—N1—C2—C3 | −77.9 (5) | H3A—C3—C4—N2 | −66.8 (5) |
H1C—N1—C2—C3 | 161.4 (6) | H3B—C3—C4—C6 | −4.1 (5) |
C6—N3—C5—H5 | −178.7 (5) | C1—C2—C3—H3A | −56.0 (5) |
C5—N3—C6—H6 | −178.8 (5) | H2—C2—C3—H3A | −175.2 (6) |
O1—C1—C2—H2 | −144.4 (4) | H3A—C3—C4—C6 | 113.4 (5) |
C4—N2—C5—N3 | −0.56 (6) | N2—C4—C6—H6 | 178.3 (6) |
C6H9N3O2 | Dx = 1.442 Mg m−3 |
Mr = 155.16 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 4787 reflections |
a = 5.1690 (3) Å | θ = 3.0–32.3° |
b = 7.3430 (5) Å | µ = 0.11 mm−1 |
c = 18.8317 (13) Å | T = 295 K |
V = 714.78 (8) Å3 | Needle, colourless |
Z = 4 | 0.2 × 0.1 × 0.1 mm |
F(000) = 328.073 |
Bruker APEX-II CCD diffractometer | 3008 independent reflections |
Radiation source: rotating anode, Bruker TXS with Helios Optics | 2569 reflections with I ≥ 2u(I) |
Multilayer optics monochromator | Rint = 0.033 |
φ scans | θmax = 36.3°, θmin = 3.0° |
Absorption correction: multi-scan SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 | h = −8→8 |
Tmin = 0.648, Tmax = 0.747 | k = −11→11 |
14091 measured reflections | l = −28→28 |
Refinement on F2 | 0 constraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.029 | w = 1/[σ2(Fo2) + (0.0206P)2 + 0.0062P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.054 | (Δ/σ)max = 0.001 |
S = 1.11 | Δρmax = 0.16 e Å−3 |
3008 reflections | Δρmin = −0.17 e Å−3 |
181 parameters | Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876-881. |
0 restraints | Absolute structure parameter: 0.1 (11) |
Refinement. Refinement using NoSpherA2, an implementation of NOn-SPHERical Atom-form-factors in Olex2. Please cite: F. Kleemiss et al. DOI 10.1039/D0SC05526C - 2020 NoSpherA2 implementation of HAR makes use of tailor-made aspherical atomic form factors calculated on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from spherical-atom form factors. The ED is calculated from a gaussian basis set single determinant SCF wavefunction - either Hartree-Fock or DFT using selected funtionals - for a fragment of the crystal. This fregment can be embedded in an electrostatic crystal field by employing cluster charges. The following options were used: SOFTWARE: ORCA PARTITIONING: NoSpherA2 INT ACCURACY: Normal METHOD: M062X BASIS SET: x2c-TZVPP CHARGE: 0 MULTIPLICITY: 1 RELATIVISTIC: DKH2 DATE: 2021-01-19_19-23-38 |
x | y | z | Uiso*/Ueq | ||
O2 | 0.32399 (8) | 0.50882 (8) | 0.24194 (3) | 0.03363 (13) | |
O1 | 0.72486 (9) | 0.50473 (10) | 0.19836 (3) | 0.03629 (14) | |
N1 | 0.91181 (11) | 0.32105 (9) | 0.31064 (3) | 0.02296 (11) | |
H1B | 1.031 (2) | 0.3861 (17) | 0.2767 (6) | 0.043 (3) | |
H1C | 0.867 (2) | 0.1949 (15) | 0.2945 (6) | 0.037 (3) | |
H1A | 1.0053 (18) | 0.3154 (16) | 0.3575 (6) | 0.032 (2) | |
N3 | 0.87440 (11) | 0.49977 (9) | 0.55355 (3) | 0.02985 (13) | |
H3 | 0.852 (3) | 0.5006 (17) | 0.6066 (7) | 0.049 (3) | |
N2 | 1.03303 (11) | 0.43961 (9) | 0.44716 (3) | 0.02938 (13) | |
C4 | 0.80827 (12) | 0.54010 (9) | 0.43947 (3) | 0.02360 (12) | |
C1 | 0.56258 (10) | 0.48232 (9) | 0.24645 (3) | 0.02192 (12) | |
C2 | 0.66536 (10) | 0.42348 (9) | 0.31972 (3) | 0.01979 (11) | |
H2 | 0.5262 (18) | 0.3325 (13) | 0.3427 (6) | 0.036 (2) | |
C6 | 0.70825 (14) | 0.57763 (11) | 0.50522 (4) | 0.02829 (14) | |
H6 | 0.546 (2) | 0.6534 (18) | 0.5216 (6) | 0.061 (4) | |
C5 | 1.06397 (14) | 0.41825 (12) | 0.51634 (4) | 0.03111 (15) | |
H5 | 1.213 (2) | 0.3449 (19) | 0.5411 (5) | 0.062 (4) | |
C3 | 0.70836 (15) | 0.59061 (11) | 0.36742 (4) | 0.02776 (14) | |
H3A | 0.835 (3) | 0.6820 (17) | 0.3409 (6) | 0.052 (3) | |
H3B | 0.526 (2) | 0.6577 (17) | 0.3719 (6) | 0.063 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.02204 (18) | 0.0425 (3) | 0.0363 (3) | 0.0018 (2) | −0.00462 (18) | 0.0138 (2) |
O1 | 0.02826 (19) | 0.0626 (4) | 0.0180 (2) | −0.0029 (2) | −0.00110 (17) | 0.0095 (2) |
N1 | 0.0238 (2) | 0.0253 (3) | 0.0198 (3) | 0.0040 (2) | −0.0001 (2) | −0.0005 (2) |
H1B | 0.032 (6) | 0.053 (9) | 0.043 (8) | 0.008 (6) | 0.018 (5) | 0.025 (6) |
H1C | 0.044 (6) | 0.014 (6) | 0.052 (7) | 0.003 (5) | 0.000 (6) | −0.016 (6) |
H1A | 0.026 (5) | 0.048 (7) | 0.022 (6) | 0.010 (5) | −0.001 (4) | 0.003 (5) |
N3 | 0.0367 (2) | 0.0362 (4) | 0.0167 (3) | −0.0030 (3) | −0.0005 (2) | −0.0013 (2) |
H3 | 0.078 (9) | 0.042 (9) | 0.027 (7) | −0.008 (9) | 0.000 (6) | 0.003 (6) |
N2 | 0.0302 (2) | 0.0383 (3) | 0.0196 (3) | 0.0079 (2) | −0.0014 (2) | −0.0004 (2) |
C4 | 0.0286 (2) | 0.0247 (3) | 0.0174 (3) | 0.0025 (2) | −0.0027 (2) | −0.0020 (2) |
C1 | 0.0212 (2) | 0.0259 (3) | 0.0187 (3) | −0.0020 (2) | −0.0036 (2) | 0.0028 (2) |
C2 | 0.0206 (2) | 0.0226 (3) | 0.0162 (3) | 0.0004 (2) | −0.00109 (19) | 0.0021 (2) |
H2 | 0.032 (5) | 0.021 (5) | 0.054 (7) | −0.011 (5) | −0.002 (5) | 0.013 (5) |
C6 | 0.0306 (3) | 0.0329 (4) | 0.0214 (3) | 0.0028 (3) | 0.0008 (2) | −0.0057 (3) |
H6 | 0.055 (7) | 0.072 (9) | 0.057 (8) | 0.022 (7) | 0.010 (6) | −0.020 (7) |
C5 | 0.0324 (3) | 0.0401 (4) | 0.0208 (3) | 0.0042 (3) | −0.0057 (3) | 0.0021 (3) |
H5 | 0.056 (6) | 0.096 (10) | 0.035 (7) | 0.030 (7) | −0.001 (6) | 0.016 (7) |
C3 | 0.0385 (3) | 0.0239 (4) | 0.0209 (3) | 0.0073 (3) | −0.0050 (3) | −0.0014 (3) |
H3A | 0.079 (8) | 0.041 (7) | 0.035 (6) | −0.018 (8) | −0.006 (6) | 0.007 (6) |
H3B | 0.066 (8) | 0.072 (9) | 0.051 (8) | 0.049 (7) | −0.022 (6) | −0.016 (7) |
O1—C1 | 1.2453 (8) | C3—H3A | 1.062 (14) |
N2—C5 | 1.3219 (9) | N1—C2 | 1.4892 (8) |
C2—C3 | 1.5370 (10) | N3—C6 | 1.3758 (10) |
N1—H1A | 1.007 (11) | C4—C6 | 1.3698 (10) |
C2—H2 | 1.073 (10) | N1—H1C | 1.002 (11) |
C6—H6 | 1.053 (11) | C3—H3B | 1.067 (11) |
O2—C1 | 1.2514 (7) | N2—C4 | 1.3839 (9) |
N3—C5 | 1.3452 (10) | C1—C2 | 1.5404 (8) |
C3—C4 | 1.4984 (10) | N3—H3 | 1.006 (13) |
N1—H1B | 1.008 (11) | C5—H5 | 1.049 (11) |
C4—N2—C5 | 105.54 (6) | C2—N1—H1B | 110.9 (7) |
O1—C1—C2 | 117.14 (5) | H1A—N1—H1C | 109.8 (9) |
N1—C2—C3 | 110.28 (5) | C6—N3—H3 | 125.6 (8) |
N2—C4—C3 | 121.07 (6) | C3—C2—H2 | 111.0 (6) |
N2—C5—N3 | 111.87 (7) | C4—C3—H3A | 111.7 (7) |
C2—N1—H1A | 109.3 (6) | N2—C5—H5 | 126.0 (5) |
H1A—N1—H1B | 106.4 (9) | C4—C6—H6 | 132.2 (6) |
C5—N3—H3 | 127.2 (8) | O1—C1—O2 | 126.44 (6) |
C1—C2—H2 | 107.7 (6) | N1—C2—C1 | 109.50 (5) |
C2—C3—H3B | 106.7 (6) | C2—C3—C4 | 112.42 (6) |
H3A—C3—H3B | 106.9 (10) | C3—C4—C6 | 129.69 (6) |
N3—C6—H6 | 121.5 (6) | C2—N1—H1C | 107.7 (6) |
C5—N3—C6 | 107.16 (6) | H1B—N1—H1C | 112.8 (9) |
O2—C1—C2 | 116.38 (5) | N1—C2—H2 | 107.8 (5) |
C1—C2—C3 | 110.45 (5) | C2—C3—H3A | 108.6 (6) |
N2—C4—C6 | 109.24 (6) | C4—C3—H3B | 110.3 (6) |
N3—C6—C4 | 106.19 (6) | N3—C5—H5 | 122.1 (5) |
C5—N2—C4—C3 | −179.52 (7) | O1—C1—C2—N1 | −27.33 (8) |
C6—N3—C5—N2 | 0.61 (9) | O2—C1—C2—C3 | −83.35 (7) |
O1—C1—C2—C3 | 94.31 (7) | C2—C3—C4—N2 | 56.24 (8) |
N1—C2—C3—C4 | −58.88 (7) | C3—C4—C6—N3 | 179.83 (7) |
C2—C3—C4—C6 | −123.32 (8) | H1A—N1—C2—H2 | −79.9 (9) |
H1A—N1—C2—C1 | 163.2 (7) | H1B—N1—C2—H2 | 163.2 (9) |
H1B—N1—C2—C1 | 46.3 (7) | H1C—N1—C2—H2 | 39.4 (9) |
H1C—N1—C2—C1 | −77.6 (7) | H3—N3—C5—N2 | 178.4 (10) |
C4—N2—C5—H5 | 178.1 (9) | H3—N3—C6—C4 | −178.3 (9) |
H3—N3—C5—H5 | −0.2 (13) | O2—C1—C2—H2 | 38.1 (6) |
H3—N3—C6—H6 | 4.0 (12) | N1—C2—C3—H3A | 65.2 (8) |
C5—N2—C4—C6 | 0.12 (8) | C1—C2—C3—H3B | 58.9 (7) |
C5—N3—C6—C4 | −0.49 (8) | H2—C2—C3—H3B | −60.6 (9) |
O2—C1—C2—N1 | 155.01 (6) | H3B—C3—C4—N2 | 175.2 (7) |
C1—C2—C3—C4 | 179.94 (5) | C3—C4—C6—H6 | −2.9 (9) |
N2—C4—C6—N3 | 0.23 (8) | N1—C2—C3—H3B | −179.9 (7) |
H1A—N1—C2—C3 | 41.5 (7) | H2—C2—C3—C4 | 60.5 (6) |
H1B—N1—C2—C3 | −75.5 (7) | H3A—C3—C4—N2 | −66.1 (8) |
H1C—N1—C2—C3 | 160.7 (7) | H3B—C3—C4—C6 | −4.4 (7) |
C6—N3—C5—H5 | −178.0 (8) | C1—C2—C3—H3A | −56.0 (8) |
C5—N3—C6—H6 | −178.1 (8) | H2—C2—C3—H3A | −175.4 (10) |
O1—C1—C2—H2 | −144.3 (6) | H3A—C3—C4—C6 | 114.3 (8) |
C4—N2—C5—N3 | −0.45 (9) | N2—C4—C6—H6 | 177.5 (9) |
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