Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229623000177/cu3183sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229623000177/cu3183Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229623000177/cu3183Isup5.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229623000177/cu3183IIsup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229623000177/cu3183IIsup6.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229623000177/cu3183IIIsup4.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229623000177/cu3183IIIsup7.cml |
CCDC references: 2234867; 2234866; 2234865
Data collection: CrystalClear (Rigaku/MSC, 2008) for (I); APEX3 (Bruker, 2016) for (II); APEX2 (Bruker, 2014) for (III). Cell refinement: CrystalClear (Rigaku/MSC, 2008) for (I); SAINT (Bruker, 2016) for (II); SAINT (Bruker, 2014) for (III). Data reduction: CrystalClear (Rigaku/MSC, 2008) for (I); SAINT (Bruker, 2016) for (II); SAINT (Bruker, 2014) for (III). For all structures, program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a). Program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b) for (I), (II); SHELXL2018 (Sheldrick, 2015b) for (III). For all structures, molecular graphics: PLATON (Spek, 2020), Mercury (Macrae et al., 2020) and POVRay (Cason, 2004); software used to prepare material for publication: PLATON (Spek, 2020) and publCIF (Westrip, 2010).
C4H5FN3O+·C6H6NO3S−·C6H7NO3S·C4H4FN3O | F(000) = 1248 |
Mr = 604.57 | Dx = 1.722 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.4147 (17) Å | Cell parameters from 4633 reflections |
b = 5.7191 (7) Å | θ = 2.3–26.6° |
c = 27.232 (3) Å | µ = 0.31 mm−1 |
β = 103.688 (5)° | T = 200 K |
V = 2332.6 (5) Å3 | Prism, colorless |
Z = 4 | 0.38 × 0.26 × 0.10 mm |
Rigaku AFC8 Mercury CCD diffractometer | 3760 reflections with I > 2σ(I) |
Radiation source: fine-focused sealed tube | Rint = 0.048 |
ω scans | θmax = 26.6°, θmin = 2.3° |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008) | h = −18→19 |
Tmin = 0.887, Tmax = 1.000 | k = −7→7 |
17219 measured reflections | l = −33→34 |
4632 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: mixed |
wR(F2) = 0.139 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0664P)2 + 1.1379P] where P = (Fo2 + 2Fc2)/3 |
4632 reflections | (Δ/σ)max < 0.001 |
412 parameters | Δρmax = 0.53 e Å−3 |
3 restraints | Δρmin = −0.53 e Å−3 |
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 | Occ. (<1) | |
S1B | 0.39981 (4) | 0.35609 (11) | 0.34526 (2) | 0.02603 (18) | |
O3B | 0.39286 (13) | 0.5410 (3) | 0.38077 (7) | 0.0346 (5) | |
O4B | 0.32945 (12) | 0.3639 (3) | 0.29896 (7) | 0.0330 (4) | |
O5B | 0.41048 (13) | 0.1239 (3) | 0.36804 (8) | 0.0364 (5) | |
C7B | 0.66464 (16) | 0.4805 (4) | 0.30380 (9) | 0.0234 (5) | |
C8B | 0.61840 (17) | 0.2751 (4) | 0.28857 (10) | 0.0267 (5) | |
H8B | 0.642199 | 0.159787 | 0.270324 | 0.032* | |
C9B | 0.53680 (17) | 0.2412 (4) | 0.30047 (9) | 0.0258 (5) | |
H9B | 0.504496 | 0.100858 | 0.290465 | 0.031* | |
C10B | 0.50151 (16) | 0.4109 (4) | 0.32700 (9) | 0.0231 (5) | |
C11B | 0.54729 (18) | 0.6198 (4) | 0.34011 (10) | 0.0276 (5) | |
H11B | 0.522545 | 0.738590 | 0.357039 | 0.033* | |
C12B | 0.62912 (18) | 0.6544 (4) | 0.32842 (10) | 0.0283 (6) | |
H12B | 0.660645 | 0.796808 | 0.337285 | 0.034* | |
N5B | 0.75216 (15) | 0.5137 (4) | 0.29307 (9) | 0.0262 (5) | |
S1A | −0.11049 (4) | 1.00102 (10) | 0.34451 (2) | 0.02413 (18) | |
O3A | −0.10929 (13) | 1.2405 (3) | 0.36420 (8) | 0.0332 (4) | |
O4A | −0.18064 (12) | 0.9736 (3) | 0.29809 (7) | 0.0304 (4) | |
O5A | −0.11483 (13) | 0.8223 (3) | 0.38134 (7) | 0.0354 (5) | |
C7A | 0.16026 (17) | 0.8754 (4) | 0.30938 (9) | 0.0241 (5) | |
C8A | 0.09189 (17) | 0.7118 (4) | 0.29546 (9) | 0.0271 (5) | |
H8A | 0.102242 | 0.570846 | 0.279306 | 0.032* | |
C9A | 0.00920 (17) | 0.7533 (4) | 0.30500 (9) | 0.0266 (5) | |
H9A | −0.036779 | 0.639763 | 0.295909 | 0.032* | |
C10A | −0.00710 (17) | 0.9626 (4) | 0.32805 (9) | 0.0233 (5) | |
C11A | 0.05967 (17) | 1.1291 (4) | 0.33979 (10) | 0.0264 (5) | |
H11A | 0.048342 | 1.273408 | 0.354402 | 0.032* | |
C12A | 0.14267 (17) | 1.0880 (4) | 0.33050 (10) | 0.0271 (5) | |
H12A | 0.187843 | 1.204279 | 0.338461 | 0.033* | |
N5A | 0.24547 (15) | 0.8330 (4) | 0.30064 (9) | 0.0280 (5) | |
N1A | 0.43160 (15) | 0.6281 (4) | 0.53699 (9) | 0.0290 (5) | |
H1A | 0.487 (2) | 0.643 (6) | 0.5296 (12) | 0.045 (9)* | |
C2A | 0.38321 (17) | 0.4348 (4) | 0.51809 (9) | 0.0261 (5) | |
O2A | 0.41349 (13) | 0.2829 (3) | 0.49428 (8) | 0.0337 (4) | |
N3A | 0.29931 (14) | 0.4140 (4) | 0.52638 (8) | 0.0252 (4) | |
H3A | 0.269 (3) | 0.286 (6) | 0.515 (2) | 0.030* | 0.53 (4) |
C4A | 0.26458 (17) | 0.5730 (4) | 0.55329 (9) | 0.0240 (5) | |
N4A | 0.18516 (16) | 0.5435 (4) | 0.56177 (9) | 0.0314 (5) | |
H4A1 | 0.156 (2) | 0.411 (6) | 0.5513 (12) | 0.035 (8)* | |
H4A2 | 0.162 (2) | 0.643 (6) | 0.5809 (13) | 0.046 (9)* | |
C5A | 0.31713 (17) | 0.7744 (4) | 0.57061 (9) | 0.0257 (5) | |
F5A | 0.28037 (11) | 0.9375 (3) | 0.59501 (6) | 0.0369 (4) | |
C6A | 0.39835 (18) | 0.7995 (4) | 0.56241 (10) | 0.0285 (5) | |
H6A | 0.432832 | 0.934829 | 0.574073 | 0.034* | |
N1B | 0.06316 (15) | −0.1503 (4) | 0.45934 (9) | 0.0281 (5) | |
H1B | 0.009 (2) | −0.159 (6) | 0.4703 (12) | 0.044 (9)* | |
C2B | 0.11622 (17) | 0.0348 (4) | 0.47817 (9) | 0.0243 (5) | |
O2B | 0.08776 (13) | 0.1941 (3) | 0.50136 (8) | 0.0332 (4) | |
N3B | 0.20093 (14) | 0.0419 (4) | 0.47090 (8) | 0.0241 (4) | |
H3B | 0.239 (3) | 0.145 (8) | 0.486 (2) | 0.029* | 0.47 (4) |
C4B | 0.23148 (17) | −0.1262 (4) | 0.44445 (9) | 0.0237 (5) | |
N4B | 0.31211 (15) | −0.1149 (4) | 0.43611 (9) | 0.0290 (5) | |
H4B1 | 0.342 (2) | 0.013 (6) | 0.4452 (11) | 0.031 (8)* | |
H4B2 | 0.332 (2) | −0.225 (6) | 0.4171 (13) | 0.048 (10)* | |
C5B | 0.17431 (18) | −0.3192 (4) | 0.42649 (10) | 0.0264 (5) | |
F5B | 0.20706 (11) | −0.4916 (3) | 0.40242 (6) | 0.0341 (4) | |
C6B | 0.09126 (17) | −0.3281 (4) | 0.43382 (10) | 0.0275 (5) | |
H6B | 0.052968 | −0.455936 | 0.421446 | 0.033* | |
H5B1 | 0.794 (2) | 0.437 (5) | 0.3160 (11) | 0.029 (7)* | |
H5B2 | 0.767 (3) | 0.679 (7) | 0.2942 (14) | 0.060 (11)* | |
H5B3 | 0.752 (2) | 0.465 (7) | 0.2606 (9) | 0.063 (12)* | |
H5A1 | 0.259 (2) | 0.691 (6) | 0.3008 (12) | 0.040 (9)* | |
H5A2 | 0.291 (2) | 0.925 (6) | 0.3216 (12) | 0.039 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1B | 0.0214 (3) | 0.0264 (3) | 0.0320 (4) | 0.0010 (2) | 0.0096 (3) | 0.0028 (2) |
O3B | 0.0301 (10) | 0.0393 (10) | 0.0384 (11) | 0.0008 (8) | 0.0163 (9) | −0.0060 (8) |
O4B | 0.0218 (9) | 0.0375 (10) | 0.0380 (11) | 0.0013 (8) | 0.0036 (8) | 0.0015 (8) |
O5B | 0.0328 (11) | 0.0318 (10) | 0.0477 (12) | 0.0007 (8) | 0.0155 (9) | 0.0145 (9) |
C7B | 0.0218 (12) | 0.0265 (12) | 0.0229 (12) | 0.0004 (9) | 0.0070 (10) | 0.0004 (9) |
C8B | 0.0250 (13) | 0.0265 (12) | 0.0293 (13) | −0.0001 (10) | 0.0080 (10) | −0.0027 (10) |
C9B | 0.0252 (13) | 0.0211 (11) | 0.0307 (13) | −0.0007 (9) | 0.0059 (10) | −0.0028 (9) |
C10B | 0.0190 (12) | 0.0265 (12) | 0.0243 (12) | 0.0010 (9) | 0.0060 (9) | 0.0021 (9) |
C11B | 0.0287 (14) | 0.0260 (12) | 0.0304 (14) | 0.0007 (10) | 0.0116 (11) | −0.0033 (10) |
C12B | 0.0278 (13) | 0.0267 (12) | 0.0309 (14) | −0.0049 (10) | 0.0082 (11) | −0.0029 (10) |
N5B | 0.0220 (11) | 0.0263 (11) | 0.0313 (12) | −0.0012 (9) | 0.0085 (9) | −0.0003 (9) |
S1A | 0.0221 (3) | 0.0239 (3) | 0.0278 (4) | −0.0005 (2) | 0.0087 (3) | −0.0001 (2) |
O3A | 0.0297 (10) | 0.0280 (9) | 0.0449 (11) | −0.0013 (8) | 0.0152 (9) | −0.0120 (8) |
O4A | 0.0239 (9) | 0.0346 (10) | 0.0310 (10) | −0.0020 (7) | 0.0029 (8) | 0.0000 (8) |
O5A | 0.0334 (11) | 0.0400 (11) | 0.0356 (11) | 0.0010 (8) | 0.0141 (9) | 0.0123 (8) |
C7A | 0.0233 (13) | 0.0285 (12) | 0.0214 (12) | 0.0033 (10) | 0.0070 (10) | 0.0024 (9) |
C8A | 0.0280 (13) | 0.0263 (12) | 0.0277 (13) | 0.0017 (10) | 0.0082 (10) | −0.0034 (10) |
C9A | 0.0263 (13) | 0.0234 (12) | 0.0295 (13) | −0.0036 (10) | 0.0052 (10) | −0.0035 (10) |
C10A | 0.0244 (12) | 0.0251 (12) | 0.0215 (12) | 0.0009 (9) | 0.0074 (10) | 0.0001 (9) |
C11A | 0.0258 (13) | 0.0236 (12) | 0.0301 (14) | −0.0013 (10) | 0.0074 (11) | −0.0037 (10) |
C12A | 0.0240 (13) | 0.0265 (12) | 0.0319 (14) | −0.0024 (10) | 0.0088 (10) | −0.0036 (10) |
N5A | 0.0246 (12) | 0.0281 (12) | 0.0324 (12) | 0.0039 (9) | 0.0087 (9) | 0.0010 (9) |
N1A | 0.0228 (11) | 0.0298 (11) | 0.0359 (12) | −0.0045 (9) | 0.0097 (10) | −0.0042 (9) |
C2A | 0.0224 (12) | 0.0283 (12) | 0.0282 (13) | −0.0005 (10) | 0.0076 (10) | −0.0006 (10) |
O2A | 0.0282 (10) | 0.0334 (10) | 0.0446 (11) | −0.0033 (8) | 0.0185 (9) | −0.0082 (8) |
N3A | 0.0234 (11) | 0.0260 (10) | 0.0280 (11) | −0.0020 (8) | 0.0095 (9) | −0.0028 (9) |
C4A | 0.0226 (12) | 0.0286 (12) | 0.0213 (12) | −0.0002 (10) | 0.0059 (10) | 0.0013 (9) |
N4A | 0.0283 (12) | 0.0321 (12) | 0.0379 (13) | −0.0072 (10) | 0.0162 (10) | −0.0100 (10) |
C5A | 0.0265 (13) | 0.0229 (12) | 0.0275 (13) | 0.0009 (10) | 0.0058 (10) | −0.0031 (9) |
F5A | 0.0360 (9) | 0.0346 (8) | 0.0428 (9) | −0.0032 (7) | 0.0145 (7) | −0.0143 (7) |
C6A | 0.0270 (13) | 0.0252 (12) | 0.0324 (14) | −0.0024 (10) | 0.0050 (11) | −0.0038 (10) |
N1B | 0.0229 (11) | 0.0295 (11) | 0.0345 (12) | −0.0054 (9) | 0.0122 (9) | −0.0073 (9) |
C2B | 0.0249 (12) | 0.0282 (12) | 0.0215 (12) | 0.0013 (10) | 0.0085 (10) | −0.0011 (9) |
O2B | 0.0265 (10) | 0.0341 (10) | 0.0429 (11) | −0.0033 (8) | 0.0157 (9) | −0.0113 (8) |
N3B | 0.0191 (10) | 0.0284 (10) | 0.0261 (11) | −0.0029 (8) | 0.0079 (8) | −0.0035 (8) |
C4B | 0.0243 (12) | 0.0277 (12) | 0.0194 (12) | 0.0009 (10) | 0.0058 (10) | 0.0009 (9) |
N4B | 0.0259 (12) | 0.0316 (12) | 0.0314 (12) | −0.0020 (10) | 0.0106 (9) | −0.0051 (9) |
C5B | 0.0298 (13) | 0.0234 (12) | 0.0266 (13) | 0.0020 (10) | 0.0080 (10) | −0.0030 (9) |
F5B | 0.0332 (9) | 0.0304 (8) | 0.0410 (9) | 0.0010 (6) | 0.0132 (7) | −0.0102 (6) |
C6B | 0.0269 (13) | 0.0245 (12) | 0.0315 (14) | −0.0041 (10) | 0.0076 (11) | −0.0044 (10) |
S1B—O3B | 1.4540 (19) | C12A—H12A | 0.9500 |
S1B—O4B | 1.456 (2) | N5A—H5A1 | 0.84 (4) |
S1B—O5B | 1.4586 (19) | N5A—H5A2 | 0.95 (4) |
S1B—C10B | 1.781 (2) | N1A—C2A | 1.364 (3) |
C7B—C12B | 1.383 (3) | N1A—C6A | 1.368 (3) |
C7B—C8B | 1.386 (3) | N1A—H1A | 0.92 (4) |
C7B—N5B | 1.459 (3) | C2A—O2A | 1.240 (3) |
C8B—C9B | 1.385 (3) | C2A—N3A | 1.370 (3) |
C8B—H8B | 0.9500 | N3A—C4A | 1.355 (3) |
C9B—C10B | 1.395 (3) | N3A—H3A | 0.88 (2) |
C9B—H9B | 0.9500 | C4A—N4A | 1.309 (3) |
C10B—C11B | 1.390 (4) | C4A—C5A | 1.423 (4) |
C11B—C12B | 1.386 (4) | N4A—H4A1 | 0.90 (3) |
C11B—H11B | 0.9500 | N4A—H4A2 | 0.90 (4) |
C12B—H12B | 0.9500 | C5A—C6A | 1.331 (4) |
N5B—H5B1 | 0.90 (3) | C5A—F5A | 1.346 (3) |
N5B—H5B2 | 0.97 (4) | C6A—H6A | 0.9500 |
N5B—H5B3 | 0.926 (19) | N1B—C6B | 1.359 (3) |
S1A—O5A | 1.4443 (19) | N1B—C2B | 1.362 (3) |
S1A—O4A | 1.465 (2) | N1B—H1B | 0.95 (4) |
S1A—O3A | 1.4695 (18) | C2B—O2B | 1.246 (3) |
S1A—C10A | 1.768 (2) | C2B—N3B | 1.367 (3) |
C7A—C8A | 1.393 (4) | N3B—C4B | 1.351 (3) |
C7A—C12A | 1.399 (3) | N3B—H3B | 0.87 (2) |
C7A—N5A | 1.410 (3) | C4B—N4B | 1.317 (3) |
C8A—C9A | 1.380 (4) | C4B—C5B | 1.425 (4) |
C8A—H8A | 0.9500 | N4B—H4B1 | 0.87 (3) |
C9A—C10A | 1.401 (3) | N4B—H4B2 | 0.91 (4) |
C9A—H9A | 0.9500 | C5B—C6B | 1.342 (4) |
C10A—C11A | 1.383 (4) | C5B—F5B | 1.347 (3) |
C11A—C12A | 1.382 (4) | C6B—H6B | 0.9500 |
C11A—H11A | 0.9500 | ||
O3B—S1B—O4B | 113.37 (12) | C10A—C11A—H11A | 119.6 |
O3B—S1B—O5B | 113.46 (12) | C11A—C12A—C7A | 120.1 (2) |
O4B—S1B—O5B | 112.46 (12) | C11A—C12A—H12A | 120.0 |
O3B—S1B—C10B | 105.42 (11) | C7A—C12A—H12A | 120.0 |
O4B—S1B—C10B | 106.09 (11) | C7A—N5A—H5A1 | 114 (2) |
O5B—S1B—C10B | 105.13 (11) | C7A—N5A—H5A2 | 112.8 (19) |
C12B—C7B—C8B | 121.3 (2) | H5A1—N5A—H5A2 | 112 (3) |
C12B—C7B—N5B | 119.7 (2) | C2A—N1A—C6A | 122.3 (2) |
C8B—C7B—N5B | 119.0 (2) | C2A—N1A—H1A | 116 (2) |
C9B—C8B—C7B | 118.7 (2) | C6A—N1A—H1A | 121 (2) |
C9B—C8B—H8B | 120.7 | O2A—C2A—N1A | 121.7 (2) |
C7B—C8B—H8B | 120.7 | O2A—C2A—N3A | 120.8 (2) |
C8B—C9B—C10B | 120.7 (2) | N1A—C2A—N3A | 117.5 (2) |
C8B—C9B—H9B | 119.6 | C4A—N3A—C2A | 122.7 (2) |
C10B—C9B—H9B | 119.6 | C4A—N3A—H3A | 120 (4) |
C11B—C10B—C9B | 119.6 (2) | C2A—N3A—H3A | 117 (4) |
C11B—C10B—S1B | 120.42 (19) | N4A—C4A—N3A | 121.0 (2) |
C9B—C10B—S1B | 119.93 (19) | N4A—C4A—C5A | 121.9 (2) |
C12B—C11B—C10B | 119.8 (2) | N3A—C4A—C5A | 117.1 (2) |
C12B—C11B—H11B | 120.1 | C4A—N4A—H4A1 | 119 (2) |
C10B—C11B—H11B | 120.1 | C4A—N4A—H4A2 | 122 (2) |
C7B—C12B—C11B | 119.7 (2) | H4A1—N4A—H4A2 | 118 (3) |
C7B—C12B—H12B | 120.2 | C6A—C5A—F5A | 122.1 (2) |
C11B—C12B—H12B | 120.2 | C6A—C5A—C4A | 121.1 (2) |
C7B—N5B—H5B1 | 110.0 (19) | F5A—C5A—C4A | 116.9 (2) |
C7B—N5B—H5B2 | 110 (2) | C5A—C6A—N1A | 119.2 (2) |
H5B1—N5B—H5B2 | 109 (3) | C5A—C6A—H6A | 120.4 |
C7B—N5B—H5B3 | 111 (2) | N1A—C6A—H6A | 120.4 |
H5B1—N5B—H5B3 | 111 (3) | C6B—N1B—C2B | 122.6 (2) |
H5B2—N5B—H5B3 | 106 (3) | C6B—N1B—H1B | 122 (2) |
O5A—S1A—O4A | 112.18 (12) | C2B—N1B—H1B | 115 (2) |
O5A—S1A—O3A | 113.88 (12) | O2B—C2B—N1B | 120.5 (2) |
O4A—S1A—O3A | 110.96 (12) | O2B—C2B—N3B | 121.0 (2) |
O5A—S1A—C10A | 106.30 (11) | N1B—C2B—N3B | 118.5 (2) |
O4A—S1A—C10A | 107.06 (11) | C4B—N3B—C2B | 121.4 (2) |
O3A—S1A—C10A | 105.91 (11) | C4B—N3B—H3B | 117 (4) |
C8A—C7A—C12A | 119.2 (2) | C2B—N3B—H3B | 121 (4) |
C8A—C7A—N5A | 120.9 (2) | N4B—C4B—N3B | 121.3 (2) |
C12A—C7A—N5A | 119.9 (2) | N4B—C4B—C5B | 120.7 (2) |
C9A—C8A—C7A | 120.4 (2) | N3B—C4B—C5B | 118.0 (2) |
C9A—C8A—H8A | 119.8 | C4B—N4B—H4B1 | 117 (2) |
C7A—C8A—H8A | 119.8 | C4B—N4B—H4B2 | 121 (2) |
C8A—C9A—C10A | 120.2 (2) | H4B1—N4B—H4B2 | 121 (3) |
C8A—C9A—H9A | 119.9 | C6B—C5B—F5B | 121.7 (2) |
C10A—C9A—H9A | 119.9 | C6B—C5B—C4B | 120.8 (2) |
C11A—C10A—C9A | 119.3 (2) | F5B—C5B—C4B | 117.5 (2) |
C11A—C10A—S1A | 121.45 (19) | C5B—C6B—N1B | 118.6 (2) |
C9A—C10A—S1A | 119.18 (19) | C5B—C6B—H6B | 120.7 |
C12A—C11A—C10A | 120.7 (2) | N1B—C6B—H6B | 120.7 |
C12A—C11A—H11A | 119.6 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O2Ai | 0.92 (4) | 1.86 (4) | 2.766 (3) | 169 (3) |
N3A—H3A···N3B | 0.88 (2) | 1.98 (3) | 2.833 (3) | 163 (5) |
N4A—H4A1···O5Aii | 0.90 (3) | 2.47 (3) | 2.958 (3) | 115 (2) |
N4A—H4A1···O2B | 0.90 (3) | 1.95 (3) | 2.790 (3) | 155 (3) |
N4A—H4A2···O3Aiii | 0.90 (4) | 1.98 (4) | 2.841 (3) | 160 (3) |
C6A—H6A···O5Bi | 0.95 | 2.57 | 3.134 (3) | 118 |
N1B—H1B···O2Biv | 0.95 (4) | 1.85 (4) | 2.792 (3) | 173 (3) |
N3B—H3B···N3A | 0.87 (2) | 1.99 (3) | 2.833 (3) | 165 (6) |
N4B—H4B1···O2A | 0.87 (3) | 2.16 (3) | 2.993 (3) | 159 (3) |
N4B—H4B2···O3Bv | 0.91 (4) | 2.02 (4) | 2.929 (3) | 172 (3) |
N5B—H5B1···O3Avi | 0.90 (3) | 2.07 (3) | 2.966 (3) | 175 (3) |
N5B—H5B2···O4Avii | 0.97 (4) | 1.86 (4) | 2.818 (3) | 168 (3) |
N5B—H5B3···N5Aviii | 0.93 (2) | 1.84 (2) | 2.761 (3) | 173 (4) |
N5A—H5A1···O4B | 0.84 (4) | 2.17 (4) | 2.984 (3) | 164 (3) |
N5A—H5A2···O5Bix | 0.95 (4) | 2.28 (4) | 3.224 (3) | 174 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) −x, −y+2, −z+1; (iv) −x, −y, −z+1; (v) x, y−1, z; (vi) x+1, y−1, z; (vii) x+1, y, z; (viii) −x+1, y−1/2, −z+1/2; (ix) x, y+1, z. |
C4H4FN3O·C11H11NO2 | F(000) = 664 |
Mr = 318.31 | Dx = 1.456 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0919 (5) Å | Cell parameters from 4429 reflections |
b = 5.2273 (3) Å | θ = 2.3–30.5° |
c = 30.5813 (18) Å | µ = 0.11 mm−1 |
β = 92.042 (2)° | T = 100 K |
V = 1452.49 (14) Å3 | Prism, colorless |
Z = 4 | 0.57 × 0.41 × 0.07 mm |
Bruker D8 Venture Photon 100 diffractometer | 2672 reflections with I > 2σ(I) |
Radiation source: Incoatec IµS | Rint = 0.044 |
φ and ω scans | θmax = 26.5°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −11→11 |
Tmin = 0.908, Tmax = 1.000 | k = −6→6 |
27046 measured reflections | l = −38→38 |
3015 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: mixed |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0374P)2 + 1.0091P] where P = (Fo2 + 2Fc2)/3 |
3015 reflections | (Δ/σ)max = 0.001 |
228 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
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 | ||
F5 | 0.99368 (9) | −0.14131 (16) | 0.40926 (3) | 0.0190 (2) | |
O2 | 0.61070 (11) | 0.2532 (2) | 0.51890 (3) | 0.0195 (2) | |
O3 | 0.64944 (12) | 0.6587 (2) | 0.56804 (4) | 0.0307 (3) | |
H3 | 0.632 (3) | 0.522 (5) | 0.5510 (8) | 0.062 (8)* | |
O4 | 0.43144 (12) | 0.5841 (2) | 0.59607 (4) | 0.0267 (3) | |
N1 | 0.66954 (13) | −0.0537 (2) | 0.47053 (4) | 0.0150 (3) | |
H1 | 0.581 (2) | −0.126 (4) | 0.4749 (6) | 0.032 (5)* | |
N3 | 0.83630 (12) | 0.2777 (2) | 0.48894 (4) | 0.0135 (2) | |
N4 | 1.05972 (13) | 0.2916 (3) | 0.45585 (4) | 0.0169 (3) | |
H4A | 1.087 (2) | 0.431 (4) | 0.4729 (6) | 0.033 (5)* | |
H4B | 1.122 (2) | 0.230 (4) | 0.4385 (6) | 0.023 (5)* | |
N7 | 0.64109 (14) | 1.4323 (3) | 0.73943 (4) | 0.0182 (3) | |
H7 | 0.690 (2) | 1.569 (4) | 0.7442 (6) | 0.032 (5)* | |
C5 | 0.89381 (15) | −0.0469 (3) | 0.43677 (4) | 0.0138 (3) | |
C6 | 0.76363 (15) | −0.1600 (3) | 0.44189 (4) | 0.0146 (3) | |
H6 | 0.737364 | −0.310366 | 0.426010 | 0.017* | |
C4 | 0.93094 (15) | 0.1788 (3) | 0.46085 (4) | 0.0132 (3) | |
C18 | 0.54465 (15) | 0.7031 (3) | 0.59592 (4) | 0.0161 (3) | |
C9 | 0.52960 (15) | 1.1191 (3) | 0.69988 (4) | 0.0148 (3) | |
C2 | 0.70412 (15) | 0.1643 (3) | 0.49362 (4) | 0.0141 (3) | |
C15 | 0.47940 (15) | 1.1090 (3) | 0.74396 (4) | 0.0151 (3) | |
C17 | 0.58444 (16) | 0.9173 (3) | 0.62711 (5) | 0.0181 (3) | |
H17A | 0.585964 | 1.080408 | 0.610676 | 0.022* | |
H17B | 0.684707 | 0.887190 | 0.639744 | 0.022* | |
C16 | 0.47806 (15) | 0.9416 (3) | 0.66397 (5) | 0.0177 (3) | |
H16A | 0.382310 | 1.003665 | 0.651723 | 0.021* | |
H16B | 0.461848 | 0.769952 | 0.676597 | 0.021* | |
C8 | 0.62694 (16) | 1.3174 (3) | 0.69865 (5) | 0.0173 (3) | |
H8 | 0.677637 | 1.369254 | 0.673504 | 0.021* | |
C14 | 0.54889 (15) | 1.3096 (3) | 0.76747 (5) | 0.0160 (3) | |
C13 | 0.52130 (16) | 1.3566 (3) | 0.81147 (5) | 0.0200 (3) | |
H13 | 0.567525 | 1.493847 | 0.826985 | 0.024* | |
C10 | 0.38174 (16) | 0.9468 (3) | 0.76515 (5) | 0.0190 (3) | |
H10 | 0.334692 | 0.809478 | 0.749864 | 0.023* | |
C11 | 0.35541 (18) | 0.9911 (3) | 0.80876 (5) | 0.0233 (3) | |
H11 | 0.290024 | 0.882277 | 0.823606 | 0.028* | |
C12 | 0.42401 (17) | 1.1948 (3) | 0.83137 (5) | 0.0233 (3) | |
H12 | 0.402907 | 1.222065 | 0.861217 | 0.028* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F5 | 0.0199 (4) | 0.0196 (4) | 0.0179 (4) | −0.0017 (3) | 0.0076 (3) | −0.0054 (3) |
O2 | 0.0157 (5) | 0.0202 (6) | 0.0230 (5) | −0.0047 (4) | 0.0065 (4) | −0.0101 (4) |
O3 | 0.0223 (6) | 0.0340 (7) | 0.0369 (7) | −0.0134 (5) | 0.0144 (5) | −0.0239 (6) |
O4 | 0.0224 (6) | 0.0320 (7) | 0.0262 (6) | −0.0128 (5) | 0.0079 (5) | −0.0140 (5) |
N1 | 0.0131 (6) | 0.0149 (6) | 0.0172 (6) | −0.0049 (5) | 0.0030 (5) | −0.0037 (5) |
N3 | 0.0137 (6) | 0.0135 (6) | 0.0132 (5) | −0.0025 (5) | 0.0011 (4) | −0.0017 (5) |
N4 | 0.0154 (6) | 0.0179 (6) | 0.0178 (6) | −0.0050 (5) | 0.0051 (5) | −0.0053 (5) |
N7 | 0.0203 (6) | 0.0151 (6) | 0.0192 (6) | −0.0032 (5) | 0.0001 (5) | −0.0041 (5) |
C5 | 0.0170 (7) | 0.0143 (7) | 0.0102 (6) | 0.0005 (5) | 0.0029 (5) | −0.0012 (5) |
C6 | 0.0183 (7) | 0.0128 (7) | 0.0126 (6) | −0.0013 (6) | −0.0001 (5) | −0.0023 (5) |
C4 | 0.0149 (6) | 0.0140 (7) | 0.0108 (6) | −0.0014 (5) | −0.0004 (5) | 0.0023 (5) |
C18 | 0.0164 (7) | 0.0171 (7) | 0.0149 (6) | −0.0013 (6) | 0.0013 (5) | −0.0021 (6) |
C9 | 0.0138 (6) | 0.0145 (7) | 0.0161 (7) | 0.0034 (5) | −0.0004 (5) | −0.0016 (5) |
C2 | 0.0144 (7) | 0.0145 (7) | 0.0134 (6) | −0.0012 (5) | 0.0004 (5) | −0.0012 (5) |
C15 | 0.0141 (6) | 0.0140 (7) | 0.0171 (7) | 0.0045 (5) | −0.0013 (5) | −0.0022 (5) |
C17 | 0.0184 (7) | 0.0175 (7) | 0.0185 (7) | −0.0051 (6) | 0.0023 (6) | −0.0051 (6) |
C16 | 0.0164 (7) | 0.0191 (7) | 0.0175 (7) | −0.0011 (6) | 0.0005 (5) | −0.0044 (6) |
C8 | 0.0195 (7) | 0.0166 (7) | 0.0158 (7) | 0.0006 (6) | 0.0010 (5) | −0.0012 (6) |
C14 | 0.0147 (6) | 0.0147 (7) | 0.0183 (7) | 0.0036 (6) | −0.0011 (5) | −0.0012 (6) |
C13 | 0.0212 (7) | 0.0209 (8) | 0.0177 (7) | 0.0039 (6) | −0.0027 (6) | −0.0062 (6) |
C10 | 0.0188 (7) | 0.0164 (7) | 0.0217 (7) | 0.0006 (6) | 0.0012 (6) | −0.0021 (6) |
C11 | 0.0252 (8) | 0.0225 (8) | 0.0225 (8) | 0.0009 (6) | 0.0062 (6) | 0.0029 (6) |
C12 | 0.0281 (8) | 0.0268 (8) | 0.0152 (7) | 0.0071 (7) | 0.0020 (6) | −0.0017 (6) |
F5—C5 | 1.3529 (15) | C9—C8 | 1.365 (2) |
O2—C2 | 1.2578 (17) | C9—C15 | 1.4393 (19) |
O3—C18 | 1.3214 (17) | C9—C16 | 1.500 (2) |
O3—H3 | 0.89 (3) | C15—C10 | 1.403 (2) |
O4—C18 | 1.2029 (18) | C15—C14 | 1.409 (2) |
N1—C6 | 1.3642 (18) | C17—C16 | 1.5165 (19) |
N1—C2 | 1.3712 (18) | C17—H17A | 0.9900 |
N1—H1 | 0.90 (2) | C17—H17B | 0.9900 |
N3—C4 | 1.3411 (17) | C16—H16A | 0.9900 |
N3—C2 | 1.3522 (18) | C16—H16B | 0.9900 |
N4—C4 | 1.3244 (18) | C8—H8 | 0.9500 |
N4—H4A | 0.93 (2) | C14—C13 | 1.399 (2) |
N4—H4B | 0.852 (19) | C13—C12 | 1.381 (2) |
N7—C14 | 1.3785 (19) | C13—H13 | 0.9500 |
N7—C8 | 1.3859 (19) | C10—C11 | 1.383 (2) |
N7—H7 | 0.85 (2) | C10—H10 | 0.9500 |
C5—C6 | 1.337 (2) | C11—C12 | 1.403 (2) |
C5—C4 | 1.425 (2) | C11—H11 | 0.9500 |
C6—H6 | 0.9500 | C12—H12 | 0.9500 |
C18—C17 | 1.506 (2) | ||
C18—O3—H3 | 113.7 (16) | C14—C15—C9 | 107.42 (13) |
C6—N1—C2 | 122.11 (12) | C18—C17—C16 | 112.82 (12) |
C6—N1—H1 | 120.5 (13) | C18—C17—H17A | 109.0 |
C2—N1—H1 | 117.3 (13) | C16—C17—H17A | 109.0 |
C4—N3—C2 | 119.45 (12) | C18—C17—H17B | 109.0 |
C4—N4—H4A | 120.5 (12) | C16—C17—H17B | 109.0 |
C4—N4—H4B | 121.0 (13) | H17A—C17—H17B | 107.8 |
H4A—N4—H4B | 118.3 (17) | C9—C16—C17 | 113.90 (12) |
C14—N7—C8 | 108.61 (13) | C9—C16—H16A | 108.8 |
C14—N7—H7 | 127.7 (13) | C17—C16—H16A | 108.8 |
C8—N7—H7 | 123.1 (13) | C9—C16—H16B | 108.8 |
C6—C5—F5 | 121.88 (13) | C17—C16—H16B | 108.8 |
C6—C5—C4 | 120.00 (12) | H16A—C16—H16B | 107.7 |
F5—C5—C4 | 118.12 (12) | C9—C8—N7 | 110.12 (13) |
C5—C6—N1 | 118.23 (13) | C9—C8—H8 | 124.9 |
C5—C6—H6 | 120.9 | N7—C8—H8 | 124.9 |
N1—C6—H6 | 120.9 | N7—C14—C13 | 130.58 (14) |
N4—C4—N3 | 119.50 (13) | N7—C14—C15 | 107.49 (12) |
N4—C4—C5 | 120.20 (12) | C13—C14—C15 | 121.93 (14) |
N3—C4—C5 | 120.30 (12) | C12—C13—C14 | 117.14 (14) |
O4—C18—O3 | 123.26 (13) | C12—C13—H13 | 121.4 |
O4—C18—C17 | 124.62 (13) | C14—C13—H13 | 121.4 |
O3—C18—C17 | 112.13 (12) | C11—C10—C15 | 118.59 (14) |
C8—C9—C15 | 106.33 (12) | C11—C10—H10 | 120.7 |
C8—C9—C16 | 129.48 (13) | C15—C10—H10 | 120.7 |
C15—C9—C16 | 124.18 (13) | C10—C11—C12 | 120.87 (15) |
O2—C2—N3 | 121.69 (13) | C10—C11—H11 | 119.6 |
O2—C2—N1 | 118.43 (12) | C12—C11—H11 | 119.6 |
N3—C2—N1 | 119.89 (12) | C13—C12—C11 | 121.85 (14) |
C10—C15—C14 | 119.60 (13) | C13—C12—H12 | 119.1 |
C10—C15—C9 | 132.98 (14) | C11—C12—H12 | 119.1 |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2 | 0.89 (3) | 1.72 (3) | 2.6150 (15) | 177 (2) |
N1—H1···O2i | 0.90 (2) | 1.89 (2) | 2.7825 (16) | 175.0 (19) |
N4—H4A···N3ii | 0.93 (2) | 2.03 (2) | 2.9494 (17) | 175.2 (18) |
N4—H4B···O3ii | 0.852 (19) | 2.174 (18) | 2.7805 (16) | 128.0 (16) |
N7—H7···N7iii | 0.85 (2) | 2.48 (2) | 3.3287 (16) | 173.1 (18) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+2, −y+1, −z+1; (iii) −x+3/2, y+1/2, −z+3/2. |
C4H8N5+·C7H4NO4− | F(000) = 1216 |
Mr = 292.27 | Dx = 1.366 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 21.581 (3) Å | Cell parameters from 9966 reflections |
b = 10.3368 (16) Å | θ = 2.5–40.3° |
c = 13.853 (2) Å | µ = 0.11 mm−1 |
β = 113.155 (5)° | T = 120 K |
V = 2841.4 (8) Å3 | Block, colourless |
Z = 8 | 0.21 × 0.19 × 0.18 mm |
Bruker APEXII diffractometer | 6174 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.045 |
ω scans | θmax = 40.3°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | h = −39→39 |
Tmin = 0.676, Tmax = 0.748 | k = −18→18 |
37277 measured reflections | l = −23→25 |
8912 independent reflections |
Refinement on F2 | 12 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.055 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.144 | w = 1/[σ2(Fo2) + (0.0703P)2 + 0.8862P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
8912 reflections | Δρmax = 0.67 e Å−3 |
222 parameters | Δρmin = −0.31 e Å−3 |
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 | Occ. (<1) | |
O1A | 0.31627 (3) | 0.36179 (6) | 0.58374 (5) | 0.01634 (11) | |
O2A | 0.41678 (3) | 0.26497 (5) | 0.65422 (5) | 0.01308 (10) | |
O3A | 0.61524 (3) | 0.49887 (7) | 0.66858 (6) | 0.02610 (15) | |
O4AA | 0.60950 (11) | 0.6997 (3) | 0.6228 (6) | 0.0315 (7) | 0.80 (2) |
O4AB | 0.6118 (5) | 0.7093 (10) | 0.6519 (14) | 0.0315 (7) | 0.20 (2) |
N6 | 0.58393 (4) | 0.60008 (7) | 0.64023 (6) | 0.01970 (14) | |
C7 | 0.41312 (4) | 0.48585 (6) | 0.60468 (6) | 0.01235 (12) | |
C8 | 0.48145 (4) | 0.48567 (7) | 0.62534 (6) | 0.01262 (12) | |
H8A | 0.506771 | 0.407719 | 0.643099 | 0.015* | |
C9 | 0.51202 (4) | 0.60189 (7) | 0.61948 (6) | 0.01567 (13) | |
C10 | 0.47763 (5) | 0.71879 (8) | 0.59618 (8) | 0.02350 (18) | |
H10A | 0.500072 | 0.796958 | 0.593583 | 0.028* | |
C11 | 0.40945 (5) | 0.71796 (8) | 0.57679 (9) | 0.0280 (2) | |
H11A | 0.384725 | 0.796657 | 0.561689 | 0.034* | |
C12 | 0.37710 (4) | 0.60197 (8) | 0.57940 (8) | 0.02084 (16) | |
H12A | 0.330126 | 0.601901 | 0.563840 | 0.025* | |
C13 | 0.37893 (4) | 0.36201 (6) | 0.61412 (6) | 0.01140 (11) | |
N1 | 0.37011 (3) | 0.13605 (6) | 0.78266 (5) | 0.01373 (11) | |
N3 | 0.40595 (3) | 0.00773 (6) | 0.93608 (5) | 0.01252 (11) | |
N2 | 0.48289 (3) | 0.10099 (7) | 0.87938 (6) | 0.01684 (13) | |
N5 | 0.25936 (4) | 0.17413 (8) | 0.67659 (7) | 0.02211 (15) | |
N4 | 0.32747 (4) | −0.07849 (7) | 0.99144 (6) | 0.01575 (12) | |
C2 | 0.41908 (4) | 0.08044 (6) | 0.86720 (6) | 0.01214 (12) | |
C6 | 0.30345 (4) | 0.11802 (7) | 0.76297 (6) | 0.01438 (13) | |
C5 | 0.28689 (4) | 0.04301 (7) | 0.83229 (6) | 0.01510 (13) | |
H5B | 0.241218 | 0.027932 | 0.821550 | 0.018* | |
C4 | 0.33982 (4) | −0.00974 (6) | 0.91869 (6) | 0.01202 (12) | |
H1B | 0.3821 (7) | 0.1791 (13) | 0.7366 (11) | 0.025 (3)* | |
H2B1 | 0.4930 (7) | 0.1544 (12) | 0.8423 (11) | 0.021 (3)* | |
H2B2 | 0.5141 (7) | 0.0704 (13) | 0.9325 (11) | 0.023 (3)* | |
H5B1 | 0.2166 (8) | 0.1687 (14) | 0.6588 (11) | 0.029 (4)* | |
H5B2 | 0.2743 (8) | 0.2294 (16) | 0.6450 (12) | 0.038 (4)* | |
H4B2 | 0.3611 (7) | −0.1235 (13) | 1.0382 (11) | 0.023 (3)* | |
H4B1 | 0.2860 (7) | −0.0901 (13) | 0.9792 (10) | 0.023 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0079 (2) | 0.0187 (2) | 0.0213 (3) | 0.00035 (17) | 0.0046 (2) | 0.00280 (19) |
O2A | 0.0099 (2) | 0.01261 (19) | 0.0168 (3) | 0.00151 (15) | 0.0054 (2) | 0.00195 (17) |
O3A | 0.0128 (3) | 0.0291 (3) | 0.0350 (4) | 0.0017 (2) | 0.0080 (3) | 0.0087 (3) |
O4AA | 0.0206 (4) | 0.0288 (5) | 0.0478 (19) | −0.0085 (3) | 0.0162 (8) | 0.0090 (8) |
O4AB | 0.0206 (4) | 0.0288 (5) | 0.0478 (19) | −0.0085 (3) | 0.0162 (8) | 0.0090 (8) |
N6 | 0.0123 (3) | 0.0240 (3) | 0.0222 (3) | −0.0039 (2) | 0.0062 (3) | 0.0046 (2) |
C7 | 0.0092 (3) | 0.0135 (2) | 0.0140 (3) | 0.00068 (19) | 0.0041 (2) | 0.0031 (2) |
C8 | 0.0099 (3) | 0.0144 (2) | 0.0132 (3) | −0.0001 (2) | 0.0042 (2) | 0.0020 (2) |
C9 | 0.0114 (3) | 0.0174 (3) | 0.0179 (3) | −0.0020 (2) | 0.0055 (3) | 0.0039 (2) |
C10 | 0.0203 (4) | 0.0164 (3) | 0.0344 (5) | −0.0009 (3) | 0.0114 (4) | 0.0092 (3) |
C11 | 0.0219 (4) | 0.0164 (3) | 0.0476 (6) | 0.0047 (3) | 0.0157 (4) | 0.0130 (3) |
C12 | 0.0139 (3) | 0.0171 (3) | 0.0324 (5) | 0.0042 (2) | 0.0100 (3) | 0.0096 (3) |
C13 | 0.0089 (3) | 0.0130 (2) | 0.0125 (3) | −0.00002 (19) | 0.0043 (2) | 0.0004 (2) |
N1 | 0.0091 (3) | 0.0172 (2) | 0.0145 (3) | 0.00043 (19) | 0.0042 (2) | 0.0050 (2) |
N3 | 0.0079 (2) | 0.0145 (2) | 0.0142 (3) | −0.00131 (17) | 0.0033 (2) | 0.00266 (19) |
N2 | 0.0082 (3) | 0.0230 (3) | 0.0185 (3) | −0.0008 (2) | 0.0044 (2) | 0.0077 (2) |
N5 | 0.0101 (3) | 0.0318 (4) | 0.0214 (4) | 0.0016 (2) | 0.0029 (3) | 0.0136 (3) |
N4 | 0.0091 (3) | 0.0202 (3) | 0.0172 (3) | −0.0014 (2) | 0.0043 (2) | 0.0066 (2) |
C2 | 0.0086 (3) | 0.0132 (2) | 0.0139 (3) | −0.00043 (19) | 0.0036 (2) | 0.0012 (2) |
C6 | 0.0092 (3) | 0.0175 (3) | 0.0151 (3) | 0.0002 (2) | 0.0033 (2) | 0.0031 (2) |
C5 | 0.0079 (3) | 0.0189 (3) | 0.0171 (3) | −0.0006 (2) | 0.0035 (3) | 0.0047 (2) |
C4 | 0.0091 (3) | 0.0122 (2) | 0.0141 (3) | −0.00125 (19) | 0.0038 (2) | 0.0009 (2) |
O1A—C13 | 1.2482 (9) | N1—C2 | 1.3585 (10) |
O2A—C13 | 1.2748 (9) | N1—C6 | 1.3676 (10) |
O3A—N6 | 1.2232 (10) | N1—H1B | 0.895 (14) |
O4AA—N6 | 1.236 (2) | N3—C2 | 1.3298 (9) |
O4AB—N6 | 1.259 (10) | N3—C4 | 1.3628 (10) |
N6—C9 | 1.4632 (11) | N2—C2 | 1.3369 (10) |
C7—C8 | 1.3874 (11) | N2—H2B1 | 0.840 (14) |
C7—C12 | 1.3977 (10) | N2—H2B2 | 0.840 (14) |
C7—C13 | 1.5088 (10) | N5—C6 | 1.3335 (11) |
C8—C9 | 1.3882 (10) | N5—H5B1 | 0.859 (15) |
C8—H8A | 0.9500 | N5—H5B2 | 0.856 (16) |
C9—C10 | 1.3881 (12) | N4—C4 | 1.3427 (10) |
C10—C11 | 1.3880 (14) | N4—H4B2 | 0.891 (14) |
C10—H10A | 0.9500 | N4—H4B1 | 0.851 (14) |
C11—C12 | 1.3950 (12) | C6—C5 | 1.3861 (11) |
C11—H11A | 0.9500 | C5—C4 | 1.3999 (11) |
C12—H12A | 0.9500 | C5—H5B | 0.9500 |
O3A—N6—O4AA | 122.86 (13) | C2—N1—C6 | 121.00 (6) |
O3A—N6—O4AB | 123.4 (5) | C2—N1—H1B | 118.7 (9) |
O3A—N6—C9 | 118.90 (7) | C6—N1—H1B | 120.1 (9) |
O4AA—N6—C9 | 118.12 (12) | C2—N3—C4 | 116.87 (6) |
O4AB—N6—C9 | 115.4 (5) | C2—N2—H2B1 | 122.0 (9) |
C8—C7—C12 | 119.61 (7) | C2—N2—H2B2 | 118.9 (10) |
C8—C7—C13 | 119.83 (6) | H2B1—N2—H2B2 | 118.2 (13) |
C12—C7—C13 | 120.50 (7) | C6—N5—H5B1 | 122.4 (10) |
C7—C8—C9 | 118.54 (7) | C6—N5—H5B2 | 118.0 (10) |
C7—C8—H8A | 120.7 | H5B1—N5—H5B2 | 118.4 (14) |
C9—C8—H8A | 120.7 | C4—N4—H4B2 | 118.4 (9) |
C10—C9—C8 | 122.96 (8) | C4—N4—H4B1 | 115.4 (9) |
C10—C9—N6 | 119.06 (7) | H4B2—N4—H4B1 | 124.3 (13) |
C8—C9—N6 | 117.98 (7) | N3—C2—N2 | 119.92 (7) |
C11—C10—C9 | 117.96 (7) | N3—C2—N1 | 123.01 (7) |
C11—C10—H10A | 121.0 | N2—C2—N1 | 117.07 (7) |
C9—C10—H10A | 121.0 | N5—C6—N1 | 116.31 (7) |
C10—C11—C12 | 120.23 (8) | N5—C6—C5 | 125.28 (8) |
C10—C11—H11A | 119.9 | N1—C6—C5 | 118.41 (7) |
C12—C11—H11A | 119.9 | C6—C5—C4 | 117.66 (7) |
C11—C12—C7 | 120.66 (8) | C6—C5—H5B | 121.2 |
C11—C12—H12A | 119.7 | C4—C5—H5B | 121.2 |
C7—C12—H12A | 119.7 | N4—C4—N3 | 116.14 (7) |
O1A—C13—O2A | 124.69 (6) | N4—C4—C5 | 120.79 (7) |
O1A—C13—C7 | 118.31 (6) | N3—C4—C5 | 123.04 (7) |
O2A—C13—C7 | 116.99 (6) | ||
C12—C7—C8—C9 | −0.42 (12) | C8—C7—C13—O1A | −172.02 (7) |
C13—C7—C8—C9 | −177.84 (7) | C12—C7—C13—O1A | 10.58 (11) |
C7—C8—C9—C10 | 1.48 (13) | C8—C7—C13—O2A | 8.85 (11) |
C7—C8—C9—N6 | −179.29 (7) | C12—C7—C13—O2A | −168.55 (8) |
O3A—N6—C9—C10 | 174.46 (9) | C4—N3—C2—N2 | −179.70 (7) |
O4AA—N6—C9—C10 | −9.3 (4) | C4—N3—C2—N1 | −0.02 (11) |
O4AB—N6—C9—C10 | 11.0 (9) | C6—N1—C2—N3 | −1.00 (11) |
O3A—N6—C9—C8 | −4.79 (12) | C6—N1—C2—N2 | 178.70 (7) |
O4AA—N6—C9—C8 | 171.4 (4) | C2—N1—C6—N5 | −178.38 (8) |
O4AB—N6—C9—C8 | −168.2 (9) | C2—N1—C6—C5 | 0.93 (11) |
C8—C9—C10—C11 | −0.79 (15) | N5—C6—C5—C4 | 179.32 (8) |
N6—C9—C10—C11 | 180.00 (9) | N1—C6—C5—C4 | 0.07 (11) |
C9—C10—C11—C12 | −0.96 (16) | C2—N3—C4—N4 | −177.10 (7) |
C10—C11—C12—C7 | 2.00 (16) | C2—N3—C4—C5 | 1.08 (11) |
C8—C7—C12—C11 | −1.28 (14) | C6—C5—C4—N4 | 176.99 (7) |
C13—C7—C12—C11 | 176.12 (9) | C6—C5—C4—N3 | −1.11 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O2A | 0.895 (14) | 1.823 (15) | 2.7139 (9) | 173.2 (13) |
N2—H2B1···O2Ai | 0.840 (14) | 2.242 (14) | 2.9276 (9) | 139.0 (12) |
N2—H2B2···N3ii | 0.840 (14) | 2.115 (14) | 2.9548 (10) | 178.7 (14) |
N5—H5B1···O4AAiii | 0.859 (15) | 2.188 (16) | 3.032 (2) | 167.4 (13) |
N5—H5B1···O4ABiii | 0.859 (15) | 2.265 (19) | 3.089 (11) | 160.6 (14) |
N5—H5B2···O1A | 0.856 (16) | 2.005 (17) | 2.8579 (10) | 174.8 (15) |
N4—H4B2···O2Aiv | 0.891 (14) | 2.156 (14) | 3.0162 (9) | 162.2 (13) |
N4—H4B1···O1Av | 0.851 (14) | 2.090 (14) | 2.9237 (10) | 166.4 (13) |
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1, −y, −z+2; (iii) x−1/2, y−1/2, z; (iv) x, −y, z+1/2; (v) −x+1/2, y−1/2, −z+3/2. |
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