Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619012087/ov3133sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619012087/ov3133Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619012087/ov3133IIIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619012087/ov3133IVsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619012087/ov3133Vsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619012087/ov3133VIsup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619012087/ov3133VIIasup7.hkl | |
Text file https://doi.org/10.1107/S2053229619012087/ov3133sup8.txt |
CCDC references: 1950912; 1950913; 1950914; 1950915; 1950916; 1950917
For all structures, data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2017); data reduction: SAINT (Bruker, 2017); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2009).
C25H22N6O | F(000) = 888 |
Mr = 422.48 | Dx = 1.281 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.7167 (10) Å | Cell parameters from 5059 reflections |
b = 16.1179 (17) Å | θ = 2.5–27.6° |
c = 13.9936 (16) Å | µ = 0.08 mm−1 |
β = 91.395 (4)° | T = 100 K |
V = 2190.9 (4) Å3 | Block, yellow |
Z = 4 | 0.17 × 0.12 × 0.07 mm |
Bruker D8 Venture diffractometer | 5058 independent reflections |
Radiation source: INCOATEC high brilliance microfocus sealed tube | 3855 reflections with I > 2σ(I) |
Multilayer mirror monochromator | Rint = 0.074 |
φ and ω scans | θmax = 27.6°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −12→12 |
Tmin = 0.804, Tmax = 0.994 | k = −20→20 |
29495 measured reflections | l = −17→18 |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.122 | w = 1/[σ2(Fo2) + (0.0386P)2 + 1.5187P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
5058 reflections | Δρmax = 0.27 e Å−3 |
300 parameters | Δρmin = −0.30 e Å−3 |
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 | ||
N1 | 0.44106 (14) | 0.28049 (9) | 0.50796 (10) | 0.0183 (3) | |
C2 | 0.46897 (15) | 0.36310 (10) | 0.50340 (11) | 0.0141 (3) | |
N3 | 0.59427 (13) | 0.39568 (8) | 0.49381 (9) | 0.0140 (3) | |
C4 | 0.69692 (15) | 0.34142 (10) | 0.48068 (11) | 0.0140 (3) | |
C5 | 0.67928 (16) | 0.25686 (10) | 0.47145 (11) | 0.0153 (3) | |
C6 | 0.54478 (17) | 0.23081 (10) | 0.49149 (12) | 0.0177 (3) | |
N21 | 0.36176 (15) | 0.41520 (9) | 0.51036 (11) | 0.0181 (3) | |
H21A | 0.276 (2) | 0.3974 (13) | 0.5106 (14) | 0.022* | |
H21B | 0.377 (2) | 0.4703 (14) | 0.5079 (14) | 0.022* | |
N41 | 0.83032 (13) | 0.37716 (8) | 0.47263 (9) | 0.0143 (3) | |
C42 | 0.95045 (16) | 0.35362 (10) | 0.52036 (12) | 0.0162 (3) | |
N43 | 1.06045 (14) | 0.38499 (9) | 0.48187 (10) | 0.0183 (3) | |
C43A | 1.01278 (16) | 0.43055 (10) | 0.40369 (12) | 0.0175 (3) | |
C44 | 1.08609 (18) | 0.47550 (11) | 0.33630 (13) | 0.0219 (4) | |
H44 | 1.1836 | 0.4792 | 0.3404 | 0.026* | |
C45 | 1.01237 (19) | 0.51431 (11) | 0.26371 (13) | 0.0237 (4) | |
H45 | 1.0601 | 0.5448 | 0.2168 | 0.028* | |
C46 | 0.86878 (18) | 0.50971 (11) | 0.25777 (12) | 0.0218 (4) | |
H46 | 0.8212 | 0.5375 | 0.2070 | 0.026* | |
C47 | 0.79399 (17) | 0.46577 (10) | 0.32380 (12) | 0.0173 (3) | |
H47 | 0.6964 | 0.4624 | 0.3196 | 0.021* | |
C47A | 0.86921 (16) | 0.42699 (10) | 0.39650 (12) | 0.0153 (3) | |
C421 | 0.95487 (17) | 0.30023 (10) | 0.60518 (12) | 0.0173 (3) | |
C422 | 0.84803 (18) | 0.29808 (11) | 0.67042 (12) | 0.0211 (4) | |
H422 | 0.7696 | 0.3326 | 0.6613 | 0.025* | |
C423 | 0.8573 (2) | 0.24526 (12) | 0.74844 (13) | 0.0276 (4) | |
H423 | 0.7851 | 0.2436 | 0.7929 | 0.033* | |
C424 | 0.9715 (2) | 0.19489 (12) | 0.76175 (13) | 0.0294 (4) | |
H424 | 0.9764 | 0.1579 | 0.8146 | 0.035* | |
C425 | 1.0785 (2) | 0.19806 (11) | 0.69859 (14) | 0.0274 (4) | |
H425 | 1.1573 | 0.1640 | 0.7086 | 0.033* | |
C426 | 1.07071 (18) | 0.25088 (11) | 0.62068 (13) | 0.0214 (4) | |
H426 | 1.1447 | 0.2534 | 0.5776 | 0.026* | |
N51 | 0.78425 (14) | 0.19982 (9) | 0.45195 (11) | 0.0184 (3) | |
H51 | 0.754 (3) | 0.1504 (17) | 0.4562 (18) | 0.049 (7)* | |
C57 | 0.85661 (19) | 0.20990 (11) | 0.36183 (13) | 0.0234 (4) | |
H57A | 0.9099 | 0.2622 | 0.3636 | 0.028* | |
H57B | 0.7887 | 0.2133 | 0.3081 | 0.028* | |
C51 | 0.95252 (16) | 0.13792 (10) | 0.34601 (12) | 0.0180 (3) | |
C52 | 0.97164 (18) | 0.10869 (11) | 0.25391 (12) | 0.0212 (4) | |
H52 | 0.9248 | 0.1345 | 0.2014 | 0.025* | |
C53 | 1.05844 (18) | 0.04218 (12) | 0.23798 (13) | 0.0241 (4) | |
H53 | 1.0715 | 0.0231 | 0.1746 | 0.029* | |
C54 | 1.12609 (18) | 0.00345 (11) | 0.31372 (14) | 0.0234 (4) | |
H54 | 1.1849 | −0.0425 | 0.3027 | 0.028* | |
C55 | 1.10746 (18) | 0.03214 (11) | 0.40543 (13) | 0.0242 (4) | |
H55 | 1.1535 | 0.0058 | 0.4578 | 0.029* | |
C56 | 1.02152 (18) | 0.09950 (11) | 0.42152 (13) | 0.0230 (4) | |
H56 | 1.0101 | 0.1192 | 0.4848 | 0.028* | |
O61 | 0.52698 (12) | 0.14793 (7) | 0.49352 (10) | 0.0279 (3) | |
C61 | 0.3919 (2) | 0.11880 (13) | 0.5156 (2) | 0.0550 (8) | |
H61A | 0.3249 | 0.1411 | 0.4689 | 0.082* | |
H61B | 0.3683 | 0.1373 | 0.5798 | 0.082* | |
H61C | 0.3903 | 0.0580 | 0.5131 | 0.082* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0146 (7) | 0.0152 (7) | 0.0250 (8) | −0.0016 (5) | 0.0029 (5) | 0.0015 (6) |
C2 | 0.0139 (7) | 0.0157 (8) | 0.0128 (7) | −0.0002 (6) | 0.0006 (6) | 0.0004 (6) |
N3 | 0.0126 (6) | 0.0136 (7) | 0.0158 (7) | 0.0003 (5) | 0.0011 (5) | −0.0012 (5) |
C4 | 0.0122 (7) | 0.0149 (8) | 0.0149 (8) | −0.0016 (6) | 0.0004 (6) | 0.0011 (6) |
C5 | 0.0143 (8) | 0.0138 (8) | 0.0177 (8) | 0.0010 (6) | 0.0003 (6) | 0.0000 (6) |
C6 | 0.0180 (8) | 0.0127 (8) | 0.0225 (9) | −0.0017 (6) | 0.0011 (6) | 0.0008 (6) |
N21 | 0.0110 (7) | 0.0158 (7) | 0.0277 (8) | −0.0011 (5) | 0.0018 (6) | −0.0012 (6) |
N41 | 0.0116 (6) | 0.0130 (6) | 0.0184 (7) | −0.0004 (5) | 0.0007 (5) | 0.0009 (5) |
C42 | 0.0142 (8) | 0.0144 (8) | 0.0201 (8) | 0.0010 (6) | −0.0003 (6) | −0.0027 (6) |
N43 | 0.0148 (7) | 0.0177 (7) | 0.0224 (7) | −0.0005 (5) | 0.0028 (5) | 0.0004 (6) |
C43A | 0.0159 (8) | 0.0153 (8) | 0.0214 (8) | −0.0006 (6) | 0.0021 (6) | −0.0023 (6) |
C44 | 0.0179 (8) | 0.0231 (9) | 0.0249 (9) | −0.0037 (7) | 0.0056 (7) | −0.0003 (7) |
C45 | 0.0283 (10) | 0.0218 (9) | 0.0214 (9) | −0.0049 (7) | 0.0073 (7) | 0.0024 (7) |
C46 | 0.0280 (9) | 0.0176 (8) | 0.0197 (9) | 0.0010 (7) | 0.0003 (7) | 0.0023 (7) |
C47 | 0.0167 (8) | 0.0142 (8) | 0.0211 (8) | −0.0002 (6) | 0.0011 (6) | −0.0017 (6) |
C47A | 0.0167 (8) | 0.0105 (7) | 0.0188 (8) | −0.0002 (6) | 0.0029 (6) | −0.0012 (6) |
C421 | 0.0183 (8) | 0.0152 (8) | 0.0182 (8) | −0.0029 (6) | −0.0034 (6) | −0.0005 (6) |
C422 | 0.0222 (9) | 0.0199 (9) | 0.0210 (9) | −0.0023 (7) | −0.0018 (7) | −0.0013 (7) |
C423 | 0.0355 (11) | 0.0274 (10) | 0.0201 (9) | −0.0088 (8) | 0.0018 (8) | −0.0008 (7) |
C424 | 0.0464 (12) | 0.0201 (9) | 0.0213 (9) | −0.0055 (8) | −0.0096 (8) | 0.0041 (7) |
C425 | 0.0326 (10) | 0.0203 (9) | 0.0287 (10) | 0.0021 (7) | −0.0111 (8) | −0.0003 (8) |
C426 | 0.0207 (9) | 0.0184 (9) | 0.0249 (9) | −0.0006 (7) | −0.0036 (7) | −0.0011 (7) |
N51 | 0.0174 (7) | 0.0121 (7) | 0.0258 (8) | 0.0010 (5) | 0.0041 (6) | 0.0007 (6) |
C57 | 0.0283 (9) | 0.0202 (9) | 0.0221 (9) | 0.0059 (7) | 0.0043 (7) | 0.0002 (7) |
C51 | 0.0162 (8) | 0.0144 (8) | 0.0233 (9) | −0.0020 (6) | 0.0020 (6) | −0.0029 (7) |
C52 | 0.0213 (9) | 0.0225 (9) | 0.0198 (9) | 0.0006 (7) | 0.0016 (7) | −0.0015 (7) |
C53 | 0.0230 (9) | 0.0263 (9) | 0.0234 (9) | 0.0004 (7) | 0.0063 (7) | −0.0078 (7) |
C54 | 0.0175 (8) | 0.0192 (9) | 0.0337 (10) | 0.0016 (7) | 0.0061 (7) | −0.0052 (7) |
C55 | 0.0224 (9) | 0.0221 (9) | 0.0281 (10) | 0.0035 (7) | −0.0011 (7) | 0.0006 (7) |
C56 | 0.0249 (9) | 0.0220 (9) | 0.0220 (9) | 0.0030 (7) | 0.0006 (7) | −0.0052 (7) |
O61 | 0.0191 (6) | 0.0117 (6) | 0.0533 (9) | −0.0037 (5) | 0.0061 (6) | 0.0007 (6) |
C61 | 0.0238 (11) | 0.0193 (10) | 0.123 (2) | −0.0071 (8) | 0.0183 (13) | 0.0063 (13) |
N1—C6 | 1.312 (2) | C422—C423 | 1.386 (3) |
N1—C2 | 1.361 (2) | C422—H422 | 0.9500 |
C2—N3 | 1.336 (2) | C423—C424 | 1.384 (3) |
C2—N21 | 1.343 (2) | C423—H423 | 0.9500 |
N3—C4 | 1.343 (2) | C424—C425 | 1.382 (3) |
C4—C5 | 1.379 (2) | C424—H424 | 0.9500 |
C4—N41 | 1.4254 (19) | C425—C426 | 1.384 (3) |
C5—N51 | 1.405 (2) | C425—H425 | 0.9500 |
C5—C6 | 1.407 (2) | C426—H426 | 0.9500 |
C6—O61 | 1.347 (2) | N51—C57 | 1.468 (2) |
N21—H21A | 0.88 (2) | N51—H51 | 0.85 (3) |
N21—H21B | 0.90 (2) | C57—C51 | 1.508 (2) |
N41—C42 | 1.384 (2) | C57—H57A | 0.9900 |
N41—C47A | 1.394 (2) | C57—H57B | 0.9900 |
C42—N43 | 1.310 (2) | C51—C56 | 1.384 (2) |
C42—C421 | 1.466 (2) | C51—C52 | 1.389 (2) |
N43—C43A | 1.388 (2) | C52—C53 | 1.385 (2) |
C43A—C47A | 1.397 (2) | C52—H52 | 0.9500 |
C43A—C44 | 1.398 (2) | C53—C54 | 1.382 (3) |
C44—C45 | 1.379 (3) | C53—H53 | 0.9500 |
C44—H44 | 0.9500 | C54—C55 | 1.380 (3) |
C45—C46 | 1.398 (3) | C54—H54 | 0.9500 |
C45—H45 | 0.9500 | C55—C56 | 1.391 (2) |
C46—C47 | 1.384 (2) | C55—H55 | 0.9500 |
C46—H46 | 0.9500 | C56—H56 | 0.9500 |
C47—C47A | 1.387 (2) | O61—C61 | 1.434 (2) |
C47—H47 | 0.9500 | C61—H61A | 0.9800 |
C421—C426 | 1.391 (2) | C61—H61B | 0.9800 |
C421—C422 | 1.399 (2) | C61—H61C | 0.9800 |
C6—N1—C2 | 115.73 (14) | C421—C422—H422 | 120.2 |
N3—C2—N21 | 118.15 (15) | C424—C423—C422 | 120.21 (18) |
N3—C2—N1 | 124.94 (14) | C424—C423—H423 | 119.9 |
N21—C2—N1 | 116.90 (14) | C422—C423—H423 | 119.9 |
C2—N3—C4 | 116.08 (14) | C425—C424—C423 | 120.36 (17) |
N3—C4—C5 | 124.43 (14) | C425—C424—H424 | 119.8 |
N3—C4—N41 | 115.31 (13) | C423—C424—H424 | 119.8 |
C5—C4—N41 | 120.21 (14) | C424—C425—C426 | 119.93 (18) |
C4—C5—N51 | 125.15 (15) | C424—C425—H425 | 120.0 |
C4—C5—C6 | 112.96 (14) | C426—C425—H425 | 120.0 |
N51—C5—C6 | 121.70 (15) | C425—C426—C421 | 120.21 (17) |
N1—C6—O61 | 120.12 (15) | C425—C426—H426 | 119.9 |
N1—C6—C5 | 125.02 (15) | C421—C426—H426 | 119.9 |
O61—C6—C5 | 114.85 (14) | C5—N51—C57 | 117.37 (14) |
C2—N21—H21A | 122.1 (13) | C5—N51—H51 | 110.3 (17) |
C2—N21—H21B | 119.1 (12) | C57—N51—H51 | 109.6 (17) |
H21A—N21—H21B | 118.4 (18) | N51—C57—C51 | 110.59 (14) |
C42—N41—C47A | 106.60 (13) | N51—C57—H57A | 109.5 |
C42—N41—C4 | 127.52 (13) | C51—C57—H57A | 109.5 |
C47A—N41—C4 | 123.87 (13) | N51—C57—H57B | 109.5 |
N43—C42—N41 | 112.51 (14) | C51—C57—H57B | 109.5 |
N43—C42—C421 | 123.46 (15) | H57A—C57—H57B | 108.1 |
N41—C42—C421 | 124.02 (14) | C56—C51—C52 | 118.91 (16) |
C42—N43—C43A | 105.57 (13) | C56—C51—C57 | 121.46 (15) |
N43—C43A—C47A | 110.39 (14) | C52—C51—C57 | 119.62 (15) |
N43—C43A—C44 | 129.81 (15) | C53—C52—C51 | 120.49 (17) |
C47A—C43A—C44 | 119.80 (16) | C53—C52—H52 | 119.8 |
C45—C44—C43A | 117.91 (16) | C51—C52—H52 | 119.8 |
C45—C44—H44 | 121.0 | C54—C53—C52 | 120.41 (16) |
C43A—C44—H44 | 121.0 | C54—C53—H53 | 119.8 |
C44—C45—C46 | 121.31 (16) | C52—C53—H53 | 119.8 |
C44—C45—H45 | 119.3 | C55—C54—C53 | 119.39 (16) |
C46—C45—H45 | 119.3 | C55—C54—H54 | 120.3 |
C47—C46—C45 | 121.80 (16) | C53—C54—H54 | 120.3 |
C47—C46—H46 | 119.1 | C54—C55—C56 | 120.32 (17) |
C45—C46—H46 | 119.1 | C54—C55—H55 | 119.8 |
C46—C47—C47A | 116.38 (15) | C56—C55—H55 | 119.8 |
C46—C47—H47 | 121.8 | C51—C56—C55 | 120.47 (16) |
C47A—C47—H47 | 121.8 | C51—C56—H56 | 119.8 |
C47—C47A—N41 | 132.26 (15) | C55—C56—H56 | 119.8 |
C47—C47A—C43A | 122.79 (15) | C6—O61—C61 | 116.59 (14) |
N41—C47A—C43A | 104.92 (14) | O61—C61—H61A | 109.5 |
C426—C421—C422 | 119.63 (16) | O61—C61—H61B | 109.5 |
C426—C421—C42 | 118.00 (15) | H61A—C61—H61B | 109.5 |
C422—C421—C42 | 122.36 (15) | O61—C61—H61C | 109.5 |
C423—C422—C421 | 119.61 (17) | H61A—C61—H61C | 109.5 |
C423—C422—H422 | 120.2 | H61B—C61—H61C | 109.5 |
C6—N1—C2—N3 | −7.4 (2) | C42—N41—C47A—C47 | 177.95 (17) |
C6—N1—C2—N21 | 173.46 (15) | C4—N41—C47A—C47 | 13.0 (3) |
N21—C2—N3—C4 | −175.69 (14) | C42—N41—C47A—C43A | −0.24 (17) |
N1—C2—N3—C4 | 5.2 (2) | C4—N41—C47A—C43A | −165.17 (14) |
C2—N3—C4—C5 | 3.7 (2) | N43—C43A—C47A—C47 | −178.79 (15) |
C2—N3—C4—N41 | −178.72 (13) | C44—C43A—C47A—C47 | 0.8 (3) |
N3—C4—C5—N51 | 175.94 (15) | N43—C43A—C47A—N41 | −0.39 (18) |
N41—C4—C5—N51 | −1.5 (2) | C44—C43A—C47A—N41 | 179.17 (15) |
N3—C4—C5—C6 | −9.0 (2) | N43—C42—C421—C426 | −29.8 (2) |
N41—C4—C5—C6 | 173.53 (14) | N41—C42—C421—C426 | 150.88 (16) |
C2—N1—C6—O61 | −179.38 (15) | N43—C42—C421—C422 | 149.67 (17) |
C2—N1—C6—C5 | 1.0 (2) | N41—C42—C421—C422 | −29.7 (2) |
C4—C5—C6—N1 | 6.6 (2) | C426—C421—C422—C423 | −1.6 (2) |
N51—C5—C6—N1 | −178.22 (16) | C42—C421—C422—C423 | 178.95 (16) |
C4—C5—C6—O61 | −173.10 (15) | C421—C422—C423—C424 | 0.0 (3) |
N51—C5—C6—O61 | 2.1 (2) | C422—C423—C424—C425 | 1.4 (3) |
N3—C4—N41—C42 | 131.28 (16) | C423—C424—C425—C426 | −1.0 (3) |
C5—C4—N41—C42 | −51.1 (2) | C424—C425—C426—C421 | −0.6 (3) |
N3—C4—N41—C47A | −67.0 (2) | C422—C421—C426—C425 | 2.0 (3) |
C5—C4—N41—C47A | 110.63 (18) | C42—C421—C426—C425 | −178.58 (16) |
C47A—N41—C42—N43 | 0.84 (18) | C4—C5—N51—C57 | −60.8 (2) |
C4—N41—C42—N43 | 165.05 (15) | C6—C5—N51—C57 | 124.62 (18) |
C47A—N41—C42—C421 | −179.74 (15) | C5—N51—C57—C51 | −172.72 (14) |
C4—N41—C42—C421 | −15.5 (3) | N51—C57—C51—C56 | −34.8 (2) |
N41—C42—N43—C43A | −1.06 (18) | N51—C57—C51—C52 | 144.62 (16) |
C421—C42—N43—C43A | 179.52 (15) | C56—C51—C52—C53 | 0.0 (3) |
C42—N43—C43A—C47A | 0.89 (19) | C57—C51—C52—C53 | −179.46 (16) |
C42—N43—C43A—C44 | −178.61 (17) | C51—C52—C53—C54 | 0.7 (3) |
N43—C43A—C44—C45 | 178.74 (17) | C52—C53—C54—C55 | −0.6 (3) |
C47A—C43A—C44—C45 | −0.7 (3) | C53—C54—C55—C56 | −0.1 (3) |
C43A—C44—C45—C46 | 0.6 (3) | C52—C51—C56—C55 | −0.7 (3) |
C44—C45—C46—C47 | −0.4 (3) | C57—C51—C56—C55 | 178.74 (17) |
C45—C46—C47—C47A | 0.4 (2) | C54—C55—C56—C51 | 0.7 (3) |
C46—C47—C47A—N41 | −178.49 (17) | N1—C6—O61—C61 | −0.9 (3) |
C46—C47—C47A—C43A | −0.6 (2) | C5—C6—O61—C61 | 178.82 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21A···N43i | 0.88 (2) | 2.13 (2) | 2.985 (2) | 162.6 (19) |
N21—H21B···N3ii | 0.90 (2) | 2.18 (2) | 3.079 (2) | 177.4 (16) |
C424—H424···Cg1iii | 0.95 | 2.67 | 3.336 (2) | 128 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) x+1/2, −y+1/2, z+1/2. |
C27H26N6O3 | F(000) = 1016 |
Mr = 482.54 | Dx = 1.317 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.8911 (13) Å | Cell parameters from 6049 reflections |
b = 9.6209 (7) Å | θ = 2.5–28.3° |
c = 15.9244 (11) Å | µ = 0.09 mm−1 |
β = 91.581 (3)° | T = 100 K |
V = 2433.7 (3) Å3 | Plate, colourless |
Z = 4 | 0.21 × 0.15 × 0.06 mm |
Bruker D8 Venture diffractometer | 6049 independent reflections |
Radiation source: INCOATEC high brilliance microfocus sealed tube | 5172 reflections with I > 2σ(I) |
Multilayer mirror monochromator | Rint = 0.051 |
φ and ω scans | θmax = 28.3°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −21→21 |
Tmin = 0.959, Tmax = 0.995 | k = −12→12 |
66322 measured reflections | l = −21→21 |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.128 | w = 1/[σ2(Fo2) + (0.0494P)2 + 1.899P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
6049 reflections | Δρmax = 0.38 e Å−3 |
337 parameters | Δρmin = −0.28 e Å−3 |
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 | ||
N1 | 0.69672 (8) | 0.57588 (13) | 0.60730 (8) | 0.0183 (3) | |
C2 | 0.62603 (9) | 0.54024 (14) | 0.56163 (9) | 0.0182 (3) | |
N3 | 0.59642 (8) | 0.41021 (12) | 0.55319 (8) | 0.0181 (3) | |
C4 | 0.63921 (9) | 0.31034 (14) | 0.59488 (9) | 0.0170 (3) | |
C5 | 0.70884 (9) | 0.33344 (15) | 0.64651 (9) | 0.0183 (3) | |
C6 | 0.73466 (9) | 0.47496 (15) | 0.64820 (9) | 0.0184 (3) | |
N21 | 0.58499 (9) | 0.64311 (14) | 0.52100 (10) | 0.0262 (3) | |
H21A | 0.5984 (13) | 0.730 (2) | 0.5321 (13) | 0.031* | |
H21B | 0.5344 (14) | 0.628 (2) | 0.4999 (13) | 0.031* | |
N41 | 0.60482 (8) | 0.17383 (12) | 0.58461 (8) | 0.0178 (3) | |
C42 | 0.64158 (9) | 0.05602 (14) | 0.55215 (9) | 0.0184 (3) | |
N43 | 0.59730 (8) | −0.05674 (13) | 0.56527 (8) | 0.0212 (3) | |
C43A | 0.52760 (10) | −0.01297 (16) | 0.60871 (10) | 0.0213 (3) | |
C44 | 0.45981 (11) | −0.08966 (18) | 0.63842 (11) | 0.0281 (4) | |
H44 | 0.4559 | −0.1872 | 0.6297 | 0.034* | |
C45 | 0.39908 (12) | −0.0185 (2) | 0.68070 (12) | 0.0334 (4) | |
H45 | 0.3519 | −0.0679 | 0.7007 | 0.040* | |
C46 | 0.40471 (12) | 0.1250 (2) | 0.69509 (12) | 0.0332 (4) | |
H46 | 0.3620 | 0.1698 | 0.7257 | 0.040* | |
C47 | 0.47110 (11) | 0.20336 (18) | 0.66579 (10) | 0.0263 (3) | |
H47 | 0.4753 | 0.3006 | 0.6753 | 0.032* | |
C47A | 0.53085 (9) | 0.13064 (16) | 0.62174 (9) | 0.0198 (3) | |
C421 | 0.72194 (10) | 0.05637 (15) | 0.50931 (10) | 0.0200 (3) | |
C422 | 0.74991 (10) | 0.16830 (15) | 0.46289 (10) | 0.0207 (3) | |
H422 | 0.7161 | 0.2496 | 0.4585 | 0.025* | |
C423 | 0.82631 (10) | 0.16390 (16) | 0.42272 (10) | 0.0228 (3) | |
H423 | 0.8446 | 0.2415 | 0.3912 | 0.027* | |
C424 | 0.87557 (10) | 0.04543 (17) | 0.42907 (11) | 0.0263 (3) | |
C425 | 0.84799 (11) | −0.06908 (18) | 0.47422 (13) | 0.0319 (4) | |
H425 | 0.8816 | −0.1507 | 0.4778 | 0.038* | |
C426 | 0.77212 (11) | −0.06387 (16) | 0.51362 (12) | 0.0273 (3) | |
H426 | 0.7534 | −0.1424 | 0.5441 | 0.033* | |
O421 | 0.95281 (8) | 0.03106 (14) | 0.39365 (9) | 0.0356 (3) | |
C427 | 0.99011 (12) | 0.1535 (2) | 0.36183 (13) | 0.0364 (4) | |
H47A | 0.9576 | 0.1857 | 0.3123 | 0.055* | |
H47B | 1.0480 | 0.1336 | 0.3461 | 0.055* | |
H47C | 0.9904 | 0.2260 | 0.4051 | 0.055* | |
N51 | 0.75636 (9) | 0.23497 (14) | 0.69262 (9) | 0.0244 (3) | |
H51 | 0.7899 (13) | 0.280 (2) | 0.7264 (13) | 0.029* | |
C57 | 0.71527 (11) | 0.12267 (17) | 0.73915 (11) | 0.0258 (3) | |
H57A | 0.6885 | 0.0561 | 0.6993 | 0.031* | |
H57B | 0.6710 | 0.1619 | 0.7747 | 0.031* | |
C51 | 0.78076 (10) | 0.04907 (16) | 0.79344 (10) | 0.0225 (3) | |
C52 | 0.75966 (10) | −0.00917 (16) | 0.87007 (10) | 0.0233 (3) | |
H52 | 0.7029 | −0.0060 | 0.8873 | 0.028* | |
C53 | 0.82029 (11) | −0.07166 (17) | 0.92157 (10) | 0.0252 (3) | |
H53 | 0.8049 | −0.1112 | 0.9736 | 0.030* | |
C54 | 0.90386 (10) | −0.07676 (16) | 0.89735 (10) | 0.0233 (3) | |
C55 | 0.92575 (11) | −0.02100 (17) | 0.82077 (10) | 0.0257 (3) | |
H55 | 0.9825 | −0.0243 | 0.8035 | 0.031* | |
C56 | 0.86372 (11) | 0.04001 (17) | 0.76919 (10) | 0.0255 (3) | |
H56 | 0.8787 | 0.0762 | 0.7162 | 0.031* | |
O541 | 0.96003 (8) | −0.13820 (13) | 0.95243 (8) | 0.0304 (3) | |
C541 | 1.04397 (12) | −0.1556 (3) | 0.92368 (14) | 0.0455 (5) | |
H54A | 1.0424 | −0.2077 | 0.8708 | 0.068* | |
H54B | 1.0775 | −0.2068 | 0.9659 | 0.068* | |
H54C | 1.0694 | −0.0642 | 0.9147 | 0.068* | |
O61 | 0.80307 (7) | 0.50128 (12) | 0.69806 (7) | 0.0246 (2) | |
C61 | 0.82886 (11) | 0.64414 (18) | 0.70656 (13) | 0.0322 (4) | |
H61A | 0.8466 | 0.6792 | 0.6521 | 0.048* | |
H61B | 0.8759 | 0.6506 | 0.7474 | 0.048* | |
H61C | 0.7816 | 0.6999 | 0.7260 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0175 (6) | 0.0132 (5) | 0.0242 (6) | −0.0012 (4) | 0.0004 (5) | −0.0003 (5) |
C2 | 0.0200 (7) | 0.0121 (6) | 0.0224 (7) | 0.0002 (5) | −0.0017 (5) | −0.0002 (5) |
N3 | 0.0196 (6) | 0.0113 (5) | 0.0232 (6) | −0.0003 (4) | −0.0033 (5) | 0.0008 (5) |
C4 | 0.0195 (7) | 0.0113 (6) | 0.0202 (7) | 0.0000 (5) | 0.0000 (5) | −0.0002 (5) |
C5 | 0.0204 (7) | 0.0138 (6) | 0.0206 (7) | 0.0012 (5) | −0.0014 (5) | 0.0010 (5) |
C6 | 0.0166 (6) | 0.0171 (7) | 0.0214 (7) | −0.0006 (5) | 0.0001 (5) | −0.0015 (5) |
N21 | 0.0275 (7) | 0.0095 (6) | 0.0407 (8) | −0.0011 (5) | −0.0130 (6) | 0.0024 (5) |
N41 | 0.0190 (6) | 0.0121 (6) | 0.0222 (6) | −0.0003 (5) | −0.0013 (5) | 0.0014 (5) |
C42 | 0.0225 (7) | 0.0115 (6) | 0.0209 (7) | 0.0000 (5) | −0.0046 (5) | 0.0013 (5) |
N43 | 0.0242 (6) | 0.0133 (6) | 0.0259 (6) | −0.0029 (5) | −0.0027 (5) | 0.0025 (5) |
C43A | 0.0235 (7) | 0.0187 (7) | 0.0214 (7) | −0.0025 (6) | −0.0043 (6) | 0.0036 (6) |
C44 | 0.0339 (9) | 0.0221 (8) | 0.0281 (8) | −0.0089 (7) | −0.0022 (7) | 0.0066 (6) |
C45 | 0.0328 (9) | 0.0357 (10) | 0.0321 (9) | −0.0126 (8) | 0.0060 (7) | 0.0078 (7) |
C46 | 0.0300 (9) | 0.0367 (10) | 0.0333 (9) | 0.0000 (7) | 0.0106 (7) | 0.0029 (8) |
C47 | 0.0295 (8) | 0.0225 (8) | 0.0270 (8) | −0.0003 (6) | 0.0025 (6) | 0.0021 (6) |
C47A | 0.0203 (7) | 0.0193 (7) | 0.0195 (7) | −0.0031 (6) | −0.0029 (5) | 0.0051 (5) |
C421 | 0.0201 (7) | 0.0153 (7) | 0.0242 (7) | −0.0004 (5) | −0.0037 (6) | −0.0027 (5) |
C422 | 0.0234 (7) | 0.0149 (7) | 0.0238 (7) | 0.0022 (6) | −0.0024 (6) | −0.0024 (5) |
C423 | 0.0246 (8) | 0.0192 (7) | 0.0245 (7) | −0.0021 (6) | −0.0007 (6) | −0.0016 (6) |
C424 | 0.0215 (8) | 0.0228 (8) | 0.0347 (9) | −0.0007 (6) | 0.0017 (6) | −0.0081 (7) |
C425 | 0.0264 (8) | 0.0177 (8) | 0.0515 (11) | 0.0046 (6) | 0.0006 (8) | −0.0013 (7) |
C426 | 0.0256 (8) | 0.0149 (7) | 0.0414 (9) | 0.0004 (6) | −0.0013 (7) | 0.0020 (6) |
O421 | 0.0257 (6) | 0.0287 (6) | 0.0531 (8) | 0.0017 (5) | 0.0106 (6) | −0.0060 (6) |
C427 | 0.0328 (9) | 0.0358 (10) | 0.0410 (10) | −0.0007 (8) | 0.0123 (8) | −0.0044 (8) |
N51 | 0.0235 (7) | 0.0174 (6) | 0.0316 (7) | −0.0007 (5) | −0.0102 (6) | 0.0058 (5) |
C57 | 0.0274 (8) | 0.0215 (7) | 0.0282 (8) | 0.0011 (6) | −0.0039 (6) | 0.0066 (6) |
C51 | 0.0264 (8) | 0.0169 (7) | 0.0239 (7) | 0.0032 (6) | −0.0052 (6) | 0.0002 (6) |
C52 | 0.0236 (7) | 0.0181 (7) | 0.0282 (8) | 0.0011 (6) | −0.0005 (6) | 0.0005 (6) |
C53 | 0.0306 (8) | 0.0199 (7) | 0.0252 (8) | 0.0001 (6) | −0.0002 (6) | 0.0053 (6) |
C54 | 0.0270 (8) | 0.0171 (7) | 0.0255 (7) | 0.0024 (6) | −0.0056 (6) | 0.0033 (6) |
C55 | 0.0265 (8) | 0.0235 (8) | 0.0272 (8) | 0.0063 (6) | 0.0009 (6) | 0.0026 (6) |
C56 | 0.0323 (9) | 0.0234 (8) | 0.0209 (7) | 0.0052 (6) | 0.0004 (6) | 0.0034 (6) |
O541 | 0.0271 (6) | 0.0310 (6) | 0.0327 (6) | 0.0027 (5) | −0.0056 (5) | 0.0127 (5) |
C541 | 0.0280 (9) | 0.0642 (14) | 0.0442 (11) | 0.0150 (9) | −0.0021 (8) | 0.0206 (10) |
O61 | 0.0216 (5) | 0.0189 (5) | 0.0329 (6) | −0.0040 (4) | −0.0082 (5) | 0.0002 (4) |
C61 | 0.0262 (8) | 0.0225 (8) | 0.0473 (11) | −0.0077 (7) | −0.0084 (7) | −0.0037 (7) |
N1—C6 | 1.3071 (19) | C424—O421 | 1.372 (2) |
N1—C2 | 1.3651 (19) | C424—C425 | 1.393 (2) |
C2—N21 | 1.3418 (19) | C425—C426 | 1.375 (3) |
C2—N3 | 1.3420 (18) | C425—H425 | 0.9500 |
N3—C4 | 1.3421 (18) | C426—H426 | 0.9500 |
C4—C5 | 1.378 (2) | O421—C427 | 1.419 (2) |
C4—N41 | 1.4302 (18) | C427—H47A | 0.9800 |
C5—N51 | 1.4057 (19) | C427—H47B | 0.9800 |
C5—C6 | 1.422 (2) | C427—H47C | 0.9800 |
C6—O61 | 1.3524 (18) | N51—C57 | 1.473 (2) |
N21—H21A | 0.88 (2) | N51—H51 | 0.86 (2) |
N21—H21B | 0.87 (2) | C57—C51 | 1.511 (2) |
N41—C42 | 1.3819 (19) | C57—H57A | 0.9900 |
N41—C47A | 1.3937 (19) | C57—H57B | 0.9900 |
C42—N43 | 1.3130 (19) | C51—C56 | 1.387 (2) |
C42—C421 | 1.464 (2) | C51—C52 | 1.392 (2) |
N43—C43A | 1.387 (2) | C52—C53 | 1.385 (2) |
C43A—C47A | 1.398 (2) | C52—H52 | 0.9500 |
C43A—C44 | 1.399 (2) | C53—C54 | 1.394 (2) |
C44—C45 | 1.375 (3) | C53—H53 | 0.9500 |
C44—H44 | 0.9500 | C54—O541 | 1.3684 (19) |
C45—C46 | 1.402 (3) | C54—C55 | 1.385 (2) |
C45—H45 | 0.9500 | C55—C56 | 1.395 (2) |
C46—C47 | 1.388 (2) | C55—H55 | 0.9500 |
C46—H46 | 0.9500 | C56—H56 | 0.9500 |
C47—C47A | 1.386 (2) | O541—C541 | 1.432 (2) |
C47—H47 | 0.9500 | C541—H54A | 0.9800 |
C421—C422 | 1.386 (2) | C541—H54B | 0.9800 |
C421—C426 | 1.406 (2) | C541—H54C | 0.9800 |
C422—C423 | 1.388 (2) | O61—C61 | 1.4395 (19) |
C422—H422 | 0.9500 | C61—H61A | 0.9800 |
C423—C424 | 1.385 (2) | C61—H61B | 0.9800 |
C423—H423 | 0.9500 | C61—H61C | 0.9800 |
C6—N1—C2 | 116.13 (12) | C426—C425—C424 | 119.93 (15) |
N21—C2—N3 | 118.35 (13) | C426—C425—H425 | 120.0 |
N21—C2—N1 | 116.98 (13) | C424—C425—H425 | 120.0 |
N3—C2—N1 | 124.65 (13) | C425—C426—C421 | 120.73 (16) |
C2—N3—C4 | 116.51 (12) | C425—C426—H426 | 119.6 |
N3—C4—C5 | 124.55 (13) | C421—C426—H426 | 119.6 |
N3—C4—N41 | 114.46 (12) | C424—O421—C427 | 116.77 (14) |
C5—C4—N41 | 120.94 (13) | O421—C427—H47A | 109.5 |
C4—C5—N51 | 127.86 (13) | O421—C427—H47B | 109.5 |
C4—C5—C6 | 113.08 (13) | H47A—C427—H47B | 109.5 |
N51—C5—C6 | 119.00 (13) | O421—C427—H47C | 109.5 |
N1—C6—O61 | 120.37 (13) | H47A—C427—H47C | 109.5 |
N1—C6—C5 | 124.96 (13) | H47B—C427—H47C | 109.5 |
O61—C6—C5 | 114.66 (13) | C5—N51—C57 | 121.19 (13) |
C2—N21—H21A | 119.6 (14) | C5—N51—H51 | 107.8 (14) |
C2—N21—H21B | 119.7 (14) | C57—N51—H51 | 109.1 (14) |
H21A—N21—H21B | 116.4 (19) | N51—C57—C51 | 108.89 (13) |
C42—N41—C47A | 106.52 (12) | N51—C57—H57A | 109.9 |
C42—N41—C4 | 129.18 (13) | C51—C57—H57A | 109.9 |
C47A—N41—C4 | 123.33 (12) | N51—C57—H57B | 109.9 |
N43—C42—N41 | 112.59 (13) | C51—C57—H57B | 109.9 |
N43—C42—C421 | 123.65 (13) | H57A—C57—H57B | 108.3 |
N41—C42—C421 | 123.75 (13) | C56—C51—C52 | 118.21 (14) |
C42—N43—C43A | 105.51 (13) | C56—C51—C57 | 121.01 (14) |
N43—C43A—C47A | 110.32 (13) | C52—C51—C57 | 120.77 (15) |
N43—C43A—C44 | 129.89 (15) | C53—C52—C51 | 120.88 (15) |
C47A—C43A—C44 | 119.78 (15) | C53—C52—H52 | 119.6 |
C45—C44—C43A | 117.42 (16) | C51—C52—H52 | 119.6 |
C45—C44—H44 | 121.3 | C52—C53—C54 | 120.26 (15) |
C43A—C44—H44 | 121.3 | C52—C53—H53 | 119.9 |
C44—C45—C46 | 121.88 (16) | C54—C53—H53 | 119.9 |
C44—C45—H45 | 119.1 | O541—C54—C55 | 123.80 (15) |
C46—C45—H45 | 119.1 | O541—C54—C53 | 116.58 (14) |
C47—C46—C45 | 121.70 (17) | C55—C54—C53 | 119.62 (14) |
C47—C46—H46 | 119.2 | C54—C55—C56 | 119.39 (16) |
C45—C46—H46 | 119.2 | C54—C55—H55 | 120.3 |
C47A—C47—C46 | 115.72 (16) | C56—C55—H55 | 120.3 |
C47A—C47—H47 | 122.1 | C51—C56—C55 | 121.61 (15) |
C46—C47—H47 | 122.1 | C51—C56—H56 | 119.2 |
C47—C47A—N41 | 131.46 (14) | C55—C56—H56 | 119.2 |
C47—C47A—C43A | 123.45 (15) | C54—O541—C541 | 116.26 (14) |
N41—C47A—C43A | 105.06 (13) | O541—C541—H54A | 109.5 |
C422—C421—C426 | 118.39 (15) | O541—C541—H54B | 109.5 |
C422—C421—C42 | 123.14 (14) | H54A—C541—H54B | 109.5 |
C426—C421—C42 | 118.44 (14) | O541—C541—H54C | 109.5 |
C421—C422—C423 | 121.29 (14) | H54A—C541—H54C | 109.5 |
C421—C422—H422 | 119.4 | H54B—C541—H54C | 109.5 |
C423—C422—H422 | 119.4 | C6—O61—C61 | 117.14 (12) |
C424—C423—C422 | 119.41 (15) | O61—C61—H61A | 109.5 |
C424—C423—H423 | 120.3 | O61—C61—H61B | 109.5 |
C422—C423—H423 | 120.3 | H61A—C61—H61B | 109.5 |
O421—C424—C423 | 124.28 (16) | O61—C61—H61C | 109.5 |
O421—C424—C425 | 115.49 (15) | H61A—C61—H61C | 109.5 |
C423—C424—C425 | 120.23 (15) | H61B—C61—H61C | 109.5 |
C6—N1—C2—N21 | 178.29 (14) | N43—C43A—C47A—C47 | −177.86 (14) |
C6—N1—C2—N3 | −3.4 (2) | C44—C43A—C47A—C47 | 2.3 (2) |
N21—C2—N3—C4 | −179.95 (14) | N43—C43A—C47A—N41 | 0.16 (16) |
N1—C2—N3—C4 | 1.7 (2) | C44—C43A—C47A—N41 | −179.70 (14) |
C2—N3—C4—C5 | 1.8 (2) | N43—C42—C421—C422 | 150.21 (15) |
C2—N3—C4—N41 | 179.42 (13) | N41—C42—C421—C422 | −31.1 (2) |
N3—C4—C5—N51 | 179.41 (15) | N43—C42—C421—C426 | −28.1 (2) |
N41—C4—C5—N51 | 2.0 (2) | N41—C42—C421—C426 | 150.63 (15) |
N3—C4—C5—C6 | −3.3 (2) | C426—C421—C422—C423 | −1.2 (2) |
N41—C4—C5—C6 | 179.31 (13) | C42—C421—C422—C423 | −179.52 (14) |
C2—N1—C6—O61 | −177.13 (13) | C421—C422—C423—C424 | 0.0 (2) |
C2—N1—C6—C5 | 1.6 (2) | C422—C423—C424—O421 | −178.43 (15) |
C4—C5—C6—N1 | 1.4 (2) | C422—C423—C424—C425 | 1.1 (2) |
N51—C5—C6—N1 | 179.02 (14) | O421—C424—C425—C426 | 178.63 (16) |
C4—C5—C6—O61 | −179.76 (13) | C423—C424—C425—C426 | −0.9 (3) |
N51—C5—C6—O61 | −2.2 (2) | C424—C425—C426—C421 | −0.3 (3) |
N3—C4—N41—C42 | 120.12 (16) | C422—C421—C426—C425 | 1.4 (2) |
C5—C4—N41—C42 | −62.2 (2) | C42—C421—C426—C425 | 179.76 (16) |
N3—C4—N41—C47A | −72.71 (18) | C423—C424—O421—C427 | 11.7 (2) |
C5—C4—N41—C47A | 104.97 (17) | C425—C424—O421—C427 | −167.85 (17) |
C47A—N41—C42—N43 | 0.22 (17) | C4—C5—N51—C57 | −42.8 (2) |
C4—N41—C42—N43 | 169.06 (14) | C6—C5—N51—C57 | 140.03 (15) |
C47A—N41—C42—C421 | −178.61 (13) | C5—N51—C57—C51 | −170.69 (14) |
C4—N41—C42—C421 | −9.8 (2) | N51—C57—C51—C56 | −30.5 (2) |
N41—C42—N43—C43A | −0.12 (17) | N51—C57—C51—C52 | 148.27 (15) |
C421—C42—N43—C43A | 178.71 (13) | C56—C51—C52—C53 | 1.5 (2) |
C42—N43—C43A—C47A | −0.03 (17) | C57—C51—C52—C53 | −177.31 (15) |
C42—N43—C43A—C44 | 179.81 (16) | C51—C52—C53—C54 | 0.2 (2) |
N43—C43A—C44—C45 | 179.39 (16) | C52—C53—C54—O541 | 178.93 (15) |
C47A—C43A—C44—C45 | −0.8 (2) | C52—C53—C54—C55 | −1.1 (2) |
C43A—C44—C45—C46 | −1.0 (3) | O541—C54—C55—C56 | −179.72 (15) |
C44—C45—C46—C47 | 1.4 (3) | C53—C54—C55—C56 | 0.3 (2) |
C45—C46—C47—C47A | 0.0 (3) | C52—C51—C56—C55 | −2.3 (2) |
C46—C47—C47A—N41 | −179.29 (16) | C57—C51—C56—C55 | 176.48 (15) |
C46—C47—C47A—C43A | −1.8 (2) | C54—C55—C56—C51 | 1.4 (3) |
C42—N41—C47A—C47 | 177.57 (16) | C55—C54—O541—C541 | −6.0 (2) |
C4—N41—C47A—C47 | 7.9 (2) | C53—C54—O541—C541 | 173.98 (17) |
C42—N41—C47A—C43A | −0.22 (15) | N1—C6—O61—C61 | 2.8 (2) |
C4—N41—C47A—C43A | −169.88 (13) | C5—C6—O61—C61 | −176.06 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21A···N43i | 0.88 (2) | 2.119 (19) | 2.9777 (19) | 165.2 (19) |
N21—H21B···N3ii | 0.88 (2) | 2.25 (2) | 3.1276 (19) | 179 (2) |
C425—H425···O541iii | 0.95 | 2.42 | 3.355 (2) | 167 |
C423—H423···Cg2iv | 0.95 | 2.73 | 3.6060 (17) | 154 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z+1; (iii) x, −y−1/2, z−1/2; (iv) x, −y+1/2, z−1/2. |
C25H20N8O5 | F(000) = 1064 |
Mr = 512.49 | Dx = 1.487 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.6614 (6) Å | Cell parameters from 5246 reflections |
b = 16.6048 (11) Å | θ = 2.5–27.5° |
c = 18.1311 (13) Å | µ = 0.11 mm−1 |
β = 97.101 (3)° | T = 100 K |
V = 2288.9 (3) Å3 | Block, orange |
Z = 4 | 0.17 × 0.15 × 0.10 mm |
Bruker D8 Venture diffractometer | 5246 independent reflections |
Radiation source: INCOATEC high brilliance microfocus sealed tube | 4667 reflections with I > 2σ(I) |
Multilayer mirror monochromator | Rint = 0.039 |
φ and ω scans | θmax = 27.5°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −9→9 |
Tmin = 0.937, Tmax = 0.984 | k = −21→21 |
58336 measured reflections | l = −23→23 |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0473P)2 + 1.8641P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
5246 reflections | Δρmax = 0.37 e Å−3 |
353 parameters | Δρmin = −0.43 e Å−3 |
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 | ||
N1 | 0.48756 (15) | 0.81443 (7) | 0.68882 (6) | 0.0146 (2) | |
C2 | 0.62442 (18) | 0.80687 (8) | 0.64864 (8) | 0.0148 (3) | |
N3 | 0.61248 (15) | 0.79614 (7) | 0.57479 (6) | 0.0153 (2) | |
C4 | 0.44918 (18) | 0.78690 (8) | 0.54030 (7) | 0.0136 (3) | |
C5 | 0.29790 (17) | 0.78807 (8) | 0.57449 (7) | 0.0140 (3) | |
C6 | 0.32969 (18) | 0.80507 (8) | 0.65162 (8) | 0.0142 (3) | |
N21 | 0.78733 (16) | 0.81348 (8) | 0.68643 (7) | 0.0193 (3) | |
H21A | 0.798 (2) | 0.8068 (11) | 0.7348 (11) | 0.023* | |
H21B | 0.877 (3) | 0.8004 (11) | 0.6609 (11) | 0.023* | |
N41 | 0.43952 (15) | 0.78111 (7) | 0.46137 (6) | 0.0137 (2) | |
C42 | 0.36591 (17) | 0.72343 (8) | 0.41202 (7) | 0.0145 (3) | |
N43 | 0.37124 (16) | 0.74409 (7) | 0.34230 (7) | 0.0169 (2) | |
C43A | 0.44908 (19) | 0.81959 (9) | 0.34455 (8) | 0.0173 (3) | |
C44 | 0.4840 (2) | 0.87041 (10) | 0.28656 (8) | 0.0242 (3) | |
H44 | 0.4574 | 0.8547 | 0.2360 | 0.029* | |
C45 | 0.5588 (2) | 0.94445 (10) | 0.30585 (9) | 0.0281 (4) | |
H45 | 0.5838 | 0.9802 | 0.2676 | 0.034* | |
C46 | 0.5991 (2) | 0.96841 (10) | 0.38037 (9) | 0.0245 (3) | |
H46 | 0.6490 | 1.0201 | 0.3912 | 0.029* | |
C47 | 0.56752 (19) | 0.91834 (9) | 0.43844 (8) | 0.0188 (3) | |
H47 | 0.5947 | 0.9341 | 0.4889 | 0.023* | |
C47A | 0.49375 (18) | 0.84374 (8) | 0.41858 (8) | 0.0152 (3) | |
C421 | 0.29762 (18) | 0.64495 (8) | 0.43257 (8) | 0.0159 (3) | |
C422 | 0.35900 (19) | 0.60603 (9) | 0.49895 (8) | 0.0182 (3) | |
H422 | 0.4385 | 0.6330 | 0.5351 | 0.022* | |
C423 | 0.3047 (2) | 0.52811 (9) | 0.51256 (8) | 0.0206 (3) | |
H423 | 0.3450 | 0.5015 | 0.5579 | 0.025* | |
C424 | 0.1902 (2) | 0.49038 (9) | 0.45830 (9) | 0.0212 (3) | |
C425 | 0.1225 (2) | 0.52835 (9) | 0.39307 (9) | 0.0230 (3) | |
H425 | 0.0410 | 0.5014 | 0.3577 | 0.028* | |
C426 | 0.1757 (2) | 0.60616 (9) | 0.38024 (8) | 0.0201 (3) | |
H426 | 0.1296 | 0.6334 | 0.3360 | 0.024* | |
N44 | 0.14400 (19) | 0.40542 (8) | 0.46861 (8) | 0.0263 (3) | |
O441 | 0.05373 (19) | 0.37147 (8) | 0.41637 (8) | 0.0371 (3) | |
O442 | 0.19797 (18) | 0.37238 (7) | 0.52743 (8) | 0.0345 (3) | |
N51 | 0.12807 (16) | 0.77767 (7) | 0.53523 (7) | 0.0159 (2) | |
H51 | 0.067 (2) | 0.7404 (11) | 0.5551 (10) | 0.019* | |
C57 | 0.02756 (19) | 0.85190 (9) | 0.51743 (8) | 0.0182 (3) | |
H57A | 0.0750 | 0.8953 | 0.5516 | 0.022* | |
H57B | −0.0969 | 0.8430 | 0.5248 | 0.022* | |
C51 | 0.03723 (18) | 0.87764 (9) | 0.43807 (8) | 0.0173 (3) | |
C52 | −0.0157 (2) | 0.82320 (9) | 0.38102 (9) | 0.0230 (3) | |
H52 | −0.0560 | 0.7712 | 0.3929 | 0.028* | |
C53 | −0.0101 (2) | 0.84395 (10) | 0.30743 (9) | 0.0260 (3) | |
H53 | −0.0425 | 0.8063 | 0.2687 | 0.031* | |
C54 | 0.0436 (2) | 0.92092 (9) | 0.29170 (8) | 0.0221 (3) | |
C55 | 0.0966 (2) | 0.97679 (9) | 0.34606 (9) | 0.0213 (3) | |
H55 | 0.1325 | 1.0293 | 0.3337 | 0.026* | |
C56 | 0.09556 (19) | 0.95360 (9) | 0.41978 (8) | 0.0195 (3) | |
H56 | 0.1355 | 0.9903 | 0.4584 | 0.023* | |
N54 | 0.0453 (2) | 0.94243 (9) | 0.21334 (8) | 0.0274 (3) | |
O541 | 0.0520 (2) | 0.88772 (9) | 0.16802 (7) | 0.0450 (4) | |
O542 | 0.0417 (2) | 1.01342 (8) | 0.19625 (7) | 0.0371 (3) | |
O61 | 0.18690 (13) | 0.81298 (6) | 0.68725 (5) | 0.0184 (2) | |
C61 | 0.2153 (2) | 0.84133 (10) | 0.76322 (8) | 0.0207 (3) | |
H61A | 0.2848 | 0.8016 | 0.7942 | 0.031* | |
H61B | 0.1015 | 0.8489 | 0.7818 | 0.031* | |
H61C | 0.2787 | 0.8927 | 0.7652 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0150 (6) | 0.0168 (6) | 0.0118 (5) | 0.0000 (4) | 0.0007 (4) | 0.0017 (4) |
C2 | 0.0151 (6) | 0.0155 (6) | 0.0136 (6) | −0.0002 (5) | 0.0007 (5) | 0.0016 (5) |
N3 | 0.0142 (6) | 0.0187 (6) | 0.0129 (5) | 0.0000 (4) | 0.0012 (4) | 0.0006 (4) |
C4 | 0.0153 (6) | 0.0135 (6) | 0.0117 (6) | −0.0001 (5) | 0.0007 (5) | 0.0002 (5) |
C5 | 0.0131 (6) | 0.0140 (6) | 0.0145 (6) | −0.0009 (5) | −0.0002 (5) | 0.0002 (5) |
C6 | 0.0139 (6) | 0.0137 (6) | 0.0152 (6) | −0.0002 (5) | 0.0032 (5) | 0.0011 (5) |
N21 | 0.0141 (6) | 0.0318 (7) | 0.0117 (6) | 0.0004 (5) | 0.0003 (5) | 0.0012 (5) |
N41 | 0.0144 (5) | 0.0147 (5) | 0.0117 (5) | −0.0017 (4) | 0.0006 (4) | −0.0001 (4) |
C42 | 0.0130 (6) | 0.0170 (6) | 0.0133 (6) | 0.0000 (5) | 0.0007 (5) | −0.0018 (5) |
N43 | 0.0179 (6) | 0.0196 (6) | 0.0132 (5) | −0.0017 (5) | 0.0016 (4) | −0.0004 (4) |
C43A | 0.0167 (7) | 0.0208 (7) | 0.0144 (6) | −0.0016 (5) | 0.0013 (5) | 0.0005 (5) |
C44 | 0.0271 (8) | 0.0311 (8) | 0.0141 (7) | −0.0062 (6) | 0.0008 (6) | 0.0038 (6) |
C45 | 0.0306 (8) | 0.0310 (9) | 0.0219 (8) | −0.0100 (7) | 0.0001 (6) | 0.0104 (6) |
C46 | 0.0251 (8) | 0.0215 (7) | 0.0256 (8) | −0.0073 (6) | −0.0026 (6) | 0.0054 (6) |
C47 | 0.0176 (7) | 0.0198 (7) | 0.0181 (7) | −0.0023 (5) | −0.0010 (5) | 0.0004 (5) |
C47A | 0.0132 (6) | 0.0182 (7) | 0.0141 (6) | 0.0003 (5) | 0.0013 (5) | 0.0020 (5) |
C421 | 0.0161 (6) | 0.0157 (6) | 0.0166 (6) | 0.0001 (5) | 0.0050 (5) | −0.0018 (5) |
C422 | 0.0204 (7) | 0.0176 (7) | 0.0166 (7) | 0.0008 (5) | 0.0021 (5) | −0.0021 (5) |
C423 | 0.0237 (7) | 0.0188 (7) | 0.0201 (7) | 0.0022 (6) | 0.0062 (6) | 0.0013 (6) |
C424 | 0.0219 (7) | 0.0155 (7) | 0.0282 (8) | −0.0025 (5) | 0.0107 (6) | −0.0019 (6) |
C425 | 0.0219 (7) | 0.0225 (7) | 0.0247 (7) | −0.0064 (6) | 0.0033 (6) | −0.0053 (6) |
C426 | 0.0207 (7) | 0.0221 (7) | 0.0172 (7) | −0.0027 (6) | 0.0011 (5) | −0.0012 (6) |
N44 | 0.0282 (7) | 0.0192 (6) | 0.0337 (8) | −0.0033 (5) | 0.0129 (6) | −0.0012 (6) |
O441 | 0.0477 (8) | 0.0258 (6) | 0.0388 (7) | −0.0170 (6) | 0.0094 (6) | −0.0050 (5) |
O442 | 0.0417 (7) | 0.0222 (6) | 0.0407 (7) | −0.0029 (5) | 0.0089 (6) | 0.0074 (5) |
N51 | 0.0132 (6) | 0.0181 (6) | 0.0157 (6) | −0.0031 (4) | −0.0004 (4) | 0.0005 (5) |
C57 | 0.0152 (6) | 0.0236 (7) | 0.0153 (6) | 0.0026 (5) | 0.0005 (5) | −0.0015 (5) |
C51 | 0.0136 (6) | 0.0207 (7) | 0.0169 (6) | 0.0029 (5) | −0.0006 (5) | −0.0013 (5) |
C52 | 0.0311 (8) | 0.0177 (7) | 0.0190 (7) | −0.0018 (6) | −0.0017 (6) | 0.0002 (6) |
C53 | 0.0374 (9) | 0.0216 (8) | 0.0174 (7) | −0.0005 (6) | −0.0028 (6) | −0.0024 (6) |
C54 | 0.0244 (8) | 0.0234 (7) | 0.0182 (7) | 0.0035 (6) | 0.0023 (6) | 0.0018 (6) |
C55 | 0.0202 (7) | 0.0187 (7) | 0.0255 (8) | 0.0004 (5) | 0.0050 (6) | 0.0005 (6) |
C56 | 0.0163 (7) | 0.0203 (7) | 0.0216 (7) | −0.0004 (5) | 0.0013 (5) | −0.0038 (6) |
N54 | 0.0330 (8) | 0.0278 (7) | 0.0218 (7) | 0.0025 (6) | 0.0041 (6) | 0.0026 (6) |
O541 | 0.0782 (11) | 0.0365 (7) | 0.0195 (6) | 0.0000 (7) | 0.0035 (6) | −0.0028 (5) |
O542 | 0.0528 (8) | 0.0285 (6) | 0.0323 (7) | 0.0053 (6) | 0.0137 (6) | 0.0103 (5) |
O61 | 0.0140 (5) | 0.0274 (5) | 0.0141 (5) | −0.0009 (4) | 0.0032 (4) | −0.0018 (4) |
C61 | 0.0196 (7) | 0.0284 (8) | 0.0149 (7) | −0.0001 (6) | 0.0050 (5) | −0.0029 (6) |
N1—C6 | 1.3192 (18) | C423—C424 | 1.385 (2) |
N1—C2 | 1.3546 (18) | C423—H423 | 0.9500 |
C2—N3 | 1.3426 (17) | C424—C425 | 1.383 (2) |
C2—N21 | 1.3520 (18) | C424—N44 | 1.4719 (19) |
N3—C4 | 1.3366 (18) | C425—C426 | 1.383 (2) |
C4—C5 | 1.3804 (19) | C425—H425 | 0.9500 |
C4—N41 | 1.4270 (17) | C426—H426 | 0.9500 |
C5—N51 | 1.4144 (17) | N44—O442 | 1.2248 (19) |
C5—C6 | 1.4179 (19) | N44—O441 | 1.2376 (19) |
C6—O61 | 1.3439 (17) | N51—C57 | 1.4680 (18) |
N21—H21A | 0.88 (2) | N51—H51 | 0.879 (19) |
N21—H21B | 0.90 (2) | C57—C51 | 1.5116 (19) |
N41—C42 | 1.3825 (17) | C57—H57A | 0.9900 |
N41—C47A | 1.3914 (18) | C57—H57B | 0.9900 |
C42—N43 | 1.3153 (18) | C51—C56 | 1.392 (2) |
C42—C421 | 1.4694 (19) | C51—C52 | 1.396 (2) |
N43—C43A | 1.3867 (19) | C52—C53 | 1.384 (2) |
C43A—C44 | 1.400 (2) | C52—H52 | 0.9500 |
C43A—C47A | 1.4021 (19) | C53—C54 | 1.383 (2) |
C44—C45 | 1.383 (2) | C53—H53 | 0.9500 |
C44—H44 | 0.9500 | C54—C55 | 1.378 (2) |
C45—C46 | 1.406 (2) | C54—N54 | 1.466 (2) |
C45—H45 | 0.9500 | C55—C56 | 1.392 (2) |
C46—C47 | 1.386 (2) | C55—H55 | 0.9500 |
C46—H46 | 0.9500 | C56—H56 | 0.9500 |
C47—C47A | 1.390 (2) | N54—O542 | 1.2184 (19) |
C47—H47 | 0.9500 | N54—O541 | 1.230 (2) |
C421—C422 | 1.395 (2) | O61—C61 | 1.4465 (17) |
C421—C426 | 1.403 (2) | C61—H61A | 0.9800 |
C422—C423 | 1.391 (2) | C61—H61B | 0.9800 |
C422—H422 | 0.9500 | C61—H61C | 0.9800 |
C6—N1—C2 | 115.83 (12) | C422—C423—H423 | 120.9 |
N3—C2—N21 | 117.45 (13) | C425—C424—C423 | 122.60 (14) |
N3—C2—N1 | 125.93 (13) | C425—C424—N44 | 118.36 (14) |
N21—C2—N1 | 116.57 (12) | C423—C424—N44 | 118.98 (14) |
C4—N3—C2 | 115.23 (12) | C426—C425—C424 | 118.87 (14) |
N3—C4—C5 | 125.28 (12) | C426—C425—H425 | 120.6 |
N3—C4—N41 | 113.98 (12) | C424—C425—H425 | 120.6 |
C5—C4—N41 | 120.60 (12) | C425—C426—C421 | 120.02 (14) |
C4—C5—N51 | 122.92 (12) | C425—C426—H426 | 120.0 |
C4—C5—C6 | 113.22 (12) | C421—C426—H426 | 120.0 |
N51—C5—C6 | 123.77 (12) | O442—N44—O441 | 123.98 (14) |
N1—C6—O61 | 119.48 (12) | O442—N44—C424 | 118.65 (14) |
N1—C6—C5 | 124.24 (12) | O441—N44—C424 | 117.37 (14) |
O61—C6—C5 | 116.28 (12) | C5—N51—C57 | 115.66 (11) |
C2—N21—H21A | 117.6 (13) | C5—N51—H51 | 112.5 (12) |
C2—N21—H21B | 115.8 (12) | C57—N51—H51 | 112.9 (12) |
H21A—N21—H21B | 119.9 (17) | N51—C57—C51 | 111.13 (11) |
C42—N41—C47A | 106.43 (11) | N51—C57—H57A | 109.4 |
C42—N41—C4 | 131.47 (12) | C51—C57—H57A | 109.4 |
C47A—N41—C4 | 121.79 (11) | N51—C57—H57B | 109.4 |
N43—C42—N41 | 112.51 (12) | C51—C57—H57B | 109.4 |
N43—C42—C421 | 121.96 (12) | H57A—C57—H57B | 108.0 |
N41—C42—C421 | 125.44 (12) | C56—C51—C52 | 118.87 (14) |
C42—N43—C43A | 105.76 (12) | C56—C51—C57 | 122.54 (13) |
N43—C43A—C44 | 130.11 (13) | C52—C51—C57 | 118.59 (13) |
N43—C43A—C47A | 109.88 (12) | C53—C52—C51 | 120.84 (14) |
C44—C43A—C47A | 120.00 (14) | C53—C52—H52 | 119.6 |
C45—C44—C43A | 117.24 (14) | C51—C52—H52 | 119.6 |
C45—C44—H44 | 121.4 | C54—C53—C52 | 118.31 (14) |
C43A—C44—H44 | 121.4 | C54—C53—H53 | 120.8 |
C44—C45—C46 | 121.97 (14) | C52—C53—H53 | 120.8 |
C44—C45—H45 | 119.0 | C55—C54—C53 | 122.92 (14) |
C46—C45—H45 | 119.0 | C55—C54—N54 | 119.48 (14) |
C47—C46—C45 | 121.48 (14) | C53—C54—N54 | 117.60 (14) |
C47—C46—H46 | 119.3 | C54—C55—C56 | 117.69 (14) |
C45—C46—H46 | 119.3 | C54—C55—H55 | 121.2 |
C46—C47—C47A | 116.18 (14) | C56—C55—H55 | 121.2 |
C46—C47—H47 | 121.9 | C55—C56—C51 | 121.29 (14) |
C47A—C47—H47 | 121.9 | C55—C56—H56 | 119.4 |
C47—C47A—N41 | 131.40 (13) | C51—C56—H56 | 119.4 |
C47—C47A—C43A | 123.11 (13) | O542—N54—O541 | 123.10 (15) |
N41—C47A—C43A | 105.40 (12) | O542—N54—C54 | 118.65 (14) |
C422—C421—C426 | 119.72 (13) | O541—N54—C54 | 118.25 (14) |
C422—C421—C42 | 122.47 (13) | C6—O61—C61 | 117.01 (11) |
C426—C421—C42 | 117.64 (13) | O61—C61—H61A | 109.5 |
C423—C422—C421 | 120.51 (14) | O61—C61—H61B | 109.5 |
C423—C422—H422 | 119.7 | H61A—C61—H61B | 109.5 |
C421—C422—H422 | 119.7 | O61—C61—H61C | 109.5 |
C424—C423—C422 | 118.18 (14) | H61A—C61—H61C | 109.5 |
C424—C423—H423 | 120.9 | H61B—C61—H61C | 109.5 |
C6—N1—C2—N3 | 4.6 (2) | N43—C43A—C47A—N41 | −0.50 (16) |
C6—N1—C2—N21 | −177.75 (13) | C44—C43A—C47A—N41 | 179.02 (14) |
N21—C2—N3—C4 | 177.58 (13) | N43—C42—C421—C422 | 149.75 (14) |
N1—C2—N3—C4 | −4.8 (2) | N41—C42—C421—C422 | −26.4 (2) |
C2—N3—C4—C5 | 0.3 (2) | N43—C42—C421—C426 | −25.5 (2) |
C2—N3—C4—N41 | 175.96 (11) | N41—C42—C421—C426 | 158.37 (14) |
N3—C4—C5—N51 | −179.77 (13) | C426—C421—C422—C423 | 2.1 (2) |
N41—C4—C5—N51 | 4.9 (2) | C42—C421—C422—C423 | −173.01 (13) |
N3—C4—C5—C6 | 3.5 (2) | C421—C422—C423—C424 | 0.7 (2) |
N41—C4—C5—C6 | −171.85 (12) | C422—C423—C424—C425 | −2.9 (2) |
C2—N1—C6—O61 | −178.90 (12) | C422—C423—C424—N44 | 174.41 (13) |
C2—N1—C6—C5 | 0.0 (2) | C423—C424—C425—C426 | 2.2 (2) |
C4—C5—C6—N1 | −3.7 (2) | N44—C424—C425—C426 | −175.09 (14) |
N51—C5—C6—N1 | 179.60 (13) | C424—C425—C426—C421 | 0.7 (2) |
C4—C5—C6—O61 | 175.28 (12) | C422—C421—C426—C425 | −2.8 (2) |
N51—C5—C6—O61 | −1.4 (2) | C42—C421—C426—C425 | 172.56 (13) |
N3—C4—N41—C42 | 125.40 (15) | C425—C424—N44—O442 | −177.24 (15) |
C5—C4—N41—C42 | −58.8 (2) | C423—C424—N44—O442 | 5.3 (2) |
N3—C4—N41—C47A | −61.90 (17) | C425—C424—N44—O441 | 3.5 (2) |
C5—C4—N41—C47A | 113.94 (15) | C423—C424—N44—O441 | −173.89 (15) |
C47A—N41—C42—N43 | 0.74 (16) | C4—C5—N51—C57 | −99.47 (15) |
C4—N41—C42—N43 | 174.27 (13) | C6—C5—N51—C57 | 76.92 (17) |
C47A—N41—C42—C421 | 177.20 (13) | C5—N51—C57—C51 | 99.45 (14) |
C4—N41—C42—C421 | −9.3 (2) | N51—C57—C51—C56 | −124.40 (14) |
N41—C42—N43—C43A | −1.04 (16) | N51—C57—C51—C52 | 56.08 (17) |
C421—C42—N43—C43A | −177.63 (13) | C56—C51—C52—C53 | 0.2 (2) |
C42—N43—C43A—C44 | −178.52 (16) | C57—C51—C52—C53 | 179.69 (15) |
C42—N43—C43A—C47A | 0.94 (16) | C51—C52—C53—C54 | −2.1 (3) |
N43—C43A—C44—C45 | 177.90 (16) | C52—C53—C54—C55 | 1.9 (3) |
C47A—C43A—C44—C45 | −1.5 (2) | C52—C53—C54—N54 | −178.78 (15) |
C43A—C44—C45—C46 | 0.1 (3) | C53—C54—C55—C56 | 0.2 (2) |
C44—C45—C46—C47 | 0.8 (3) | N54—C54—C55—C56 | −179.06 (14) |
C45—C46—C47—C47A | −0.2 (2) | C54—C55—C56—C51 | −2.2 (2) |
C46—C47—C47A—N41 | −177.19 (15) | C52—C51—C56—C55 | 2.1 (2) |
C46—C47—C47A—C43A | −1.3 (2) | C57—C51—C56—C55 | −177.44 (13) |
C42—N41—C47A—C47 | 176.32 (15) | C55—C54—N54—O542 | −21.6 (2) |
C4—N41—C47A—C47 | 2.0 (2) | C53—C54—N54—O542 | 159.07 (16) |
C42—N41—C47A—C43A | −0.11 (15) | C55—C54—N54—O541 | 157.66 (16) |
C4—N41—C47A—C43A | −174.41 (12) | C53—C54—N54—O541 | −21.6 (2) |
N43—C43A—C47A—C47 | −177.31 (13) | N1—C6—O61—C61 | 7.45 (19) |
C44—C43A—C47A—C47 | 2.2 (2) | C5—C6—O61—C61 | −171.57 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21A···N43i | 0.88 (2) | 2.14 (2) | 2.9774 (18) | 160.7 (16) |
N21—H21B···O61ii | 0.90 (2) | 2.37 (2) | 3.0595 (16) | 133.1 (16) |
N51—H51···O441iii | 0.879 (17) | 2.166 (18) | 3.0241 (18) | 165.0 (16) |
C53—H53···N1iv | 0.95 | 2.50 | 3.396 (2) | 157 |
C422—H422···O541i | 0.95 | 2.48 | 3.236 (2) | 136 |
Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) x+1, y, z; (iii) −x, −y+1, −z+1; (iv) x−1/2, −y+3/2, z−1/2. |
C19H18N6O·H2O | Z = 2 |
Mr = 364.41 | F(000) = 384 |
Triclinic, P1 | Dx = 1.361 Mg m−3 |
a = 8.1992 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.0160 (8) Å | Cell parameters from 4063 reflections |
c = 11.4240 (9) Å | θ = 2.3–27.5° |
α = 109.105 (3)° | µ = 0.09 mm−1 |
β = 109.171 (3)° | T = 100 K |
γ = 97.138 (3)° | Block, colourles |
V = 889.35 (12) Å3 | 0.25 × 0.25 × 0.22 mm |
Bruker D8 Venture diffractometer | 4062 independent reflections |
Radiation source: INCOATEC high brilliance microfocus sealed tube | 3658 reflections with I > 2σ(I) |
Multilayer mirror monochromator | Rint = 0.036 |
φ and ω scans | θmax = 27.5°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −10→10 |
Tmin = 0.964, Tmax = 0.980 | k = −14→14 |
45501 measured reflections | l = −14→14 |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.0447P)2 + 0.5045P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
4062 reflections | Δρmax = 0.31 e Å−3 |
264 parameters | Δρmin = −0.35 e Å−3 |
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 | ||
N1 | 0.40225 (13) | 0.33365 (9) | 0.92094 (9) | 0.0143 (2) | |
C2 | 0.25364 (15) | 0.36368 (11) | 0.85219 (11) | 0.0137 (2) | |
N3 | 0.20172 (13) | 0.35272 (9) | 0.72400 (9) | 0.01378 (19) | |
C4 | 0.31130 (15) | 0.31190 (10) | 0.66318 (11) | 0.0129 (2) | |
C5 | 0.46866 (15) | 0.28374 (11) | 0.72253 (11) | 0.0135 (2) | |
C6 | 0.50625 (15) | 0.29744 (10) | 0.85722 (11) | 0.0137 (2) | |
N21 | 0.14698 (14) | 0.40296 (10) | 0.91704 (10) | 0.0171 (2) | |
H21A | 0.056 (2) | 0.4355 (15) | 0.8766 (15) | 0.021* | |
H21B | 0.183 (2) | 0.4186 (15) | 1.0037 (16) | 0.021* | |
N41 | 0.25100 (13) | 0.29007 (9) | 0.52339 (9) | 0.01324 (19) | |
C42 | 0.21619 (14) | 0.38007 (11) | 0.46339 (11) | 0.0130 (2) | |
N43 | 0.12910 (13) | 0.32076 (9) | 0.33160 (9) | 0.0145 (2) | |
C43A | 0.10150 (15) | 0.18494 (11) | 0.30189 (11) | 0.0144 (2) | |
C44 | 0.01439 (16) | 0.07561 (12) | 0.17852 (12) | 0.0184 (2) | |
H44 | −0.0347 | 0.0875 | 0.0965 | 0.022* | |
C45 | 0.00212 (16) | −0.05079 (12) | 0.17997 (12) | 0.0197 (2) | |
H45 | −0.0566 | −0.1263 | 0.0974 | 0.024* | |
C46 | 0.07440 (16) | −0.06958 (11) | 0.30048 (12) | 0.0184 (2) | |
H46 | 0.0623 | −0.1575 | 0.2978 | 0.022* | |
C47 | 0.16313 (15) | 0.03751 (11) | 0.42343 (12) | 0.0166 (2) | |
H47 | 0.2127 | 0.0254 | 0.5053 | 0.020* | |
C47A | 0.17567 (15) | 0.16383 (11) | 0.42058 (11) | 0.0138 (2) | |
C421 | 0.27619 (15) | 0.52499 (11) | 0.53883 (11) | 0.0134 (2) | |
C422 | 0.43789 (15) | 0.58486 (11) | 0.65114 (12) | 0.0161 (2) | |
H422 | 0.5103 | 0.5315 | 0.6813 | 0.019* | |
C423 | 0.49301 (16) | 0.72227 (12) | 0.71887 (12) | 0.0182 (2) | |
H423 | 0.6038 | 0.7619 | 0.7946 | 0.022* | |
C424 | 0.38859 (16) | 0.80323 (11) | 0.67770 (12) | 0.0182 (2) | |
C425 | 0.22742 (16) | 0.74242 (11) | 0.56505 (12) | 0.0167 (2) | |
H425 | 0.1547 | 0.7959 | 0.5354 | 0.020* | |
C426 | 0.17137 (15) | 0.60504 (11) | 0.49551 (11) | 0.0145 (2) | |
H426 | 0.0618 | 0.5655 | 0.4186 | 0.017* | |
C427 | 0.4488 (2) | 0.95229 (13) | 0.75377 (15) | 0.0284 (3) | |
H47A | 0.3440 | 0.9877 | 0.7489 | 0.043* | |
H47B | 0.5175 | 0.9921 | 0.7136 | 0.043* | |
H47C | 0.5240 | 0.9738 | 0.8483 | 0.043* | |
N51 | 0.59367 (14) | 0.25492 (10) | 0.66395 (11) | 0.0178 (2) | |
H51A | 0.657 (2) | 0.2022 (16) | 0.6950 (15) | 0.021* | |
H51B | 0.546 (2) | 0.2219 (15) | 0.5727 (17) | 0.021* | |
O61 | 0.65871 (11) | 0.26926 (8) | 0.91703 (8) | 0.01699 (18) | |
C61 | 0.70010 (17) | 0.27876 (13) | 1.05313 (12) | 0.0209 (3) | |
H61A | 0.6157 | 0.2071 | 1.0526 | 0.031* | |
H61B | 0.6906 | 0.3650 | 1.1079 | 0.031* | |
H61C | 0.8221 | 0.2706 | 1.0914 | 0.031* | |
O1 | 0.15431 (12) | 0.48181 (9) | 0.18498 (9) | 0.01827 (18) | |
H1A | 0.144 (2) | 0.4325 (17) | 0.2297 (17) | 0.027* | |
H1B | 0.225 (2) | 0.5596 (18) | 0.2457 (17) | 0.027* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0166 (5) | 0.0127 (4) | 0.0125 (4) | 0.0034 (4) | 0.0044 (4) | 0.0053 (4) |
C2 | 0.0166 (5) | 0.0105 (5) | 0.0135 (5) | 0.0021 (4) | 0.0057 (4) | 0.0048 (4) |
N3 | 0.0153 (4) | 0.0136 (4) | 0.0127 (4) | 0.0044 (3) | 0.0053 (4) | 0.0055 (4) |
C4 | 0.0167 (5) | 0.0104 (5) | 0.0117 (5) | 0.0022 (4) | 0.0055 (4) | 0.0049 (4) |
C5 | 0.0154 (5) | 0.0111 (5) | 0.0144 (5) | 0.0029 (4) | 0.0069 (4) | 0.0046 (4) |
C6 | 0.0143 (5) | 0.0097 (5) | 0.0145 (5) | 0.0017 (4) | 0.0032 (4) | 0.0048 (4) |
N21 | 0.0194 (5) | 0.0213 (5) | 0.0132 (5) | 0.0089 (4) | 0.0077 (4) | 0.0075 (4) |
N41 | 0.0171 (4) | 0.0112 (4) | 0.0119 (4) | 0.0039 (3) | 0.0059 (4) | 0.0048 (4) |
C42 | 0.0135 (5) | 0.0145 (5) | 0.0143 (5) | 0.0052 (4) | 0.0074 (4) | 0.0074 (4) |
N43 | 0.0168 (5) | 0.0144 (5) | 0.0136 (5) | 0.0045 (4) | 0.0071 (4) | 0.0057 (4) |
C43A | 0.0160 (5) | 0.0145 (5) | 0.0154 (5) | 0.0051 (4) | 0.0082 (4) | 0.0066 (4) |
C44 | 0.0214 (6) | 0.0185 (6) | 0.0140 (5) | 0.0051 (4) | 0.0064 (4) | 0.0056 (4) |
C45 | 0.0220 (6) | 0.0154 (5) | 0.0166 (6) | 0.0025 (4) | 0.0063 (5) | 0.0021 (4) |
C46 | 0.0201 (6) | 0.0132 (5) | 0.0217 (6) | 0.0038 (4) | 0.0088 (5) | 0.0062 (5) |
C47 | 0.0193 (6) | 0.0153 (5) | 0.0165 (5) | 0.0048 (4) | 0.0073 (4) | 0.0076 (4) |
C47A | 0.0150 (5) | 0.0139 (5) | 0.0128 (5) | 0.0040 (4) | 0.0069 (4) | 0.0041 (4) |
C421 | 0.0163 (5) | 0.0134 (5) | 0.0137 (5) | 0.0040 (4) | 0.0089 (4) | 0.0063 (4) |
C422 | 0.0161 (5) | 0.0161 (5) | 0.0176 (5) | 0.0050 (4) | 0.0071 (4) | 0.0077 (4) |
C423 | 0.0179 (5) | 0.0166 (5) | 0.0175 (6) | 0.0007 (4) | 0.0066 (4) | 0.0052 (4) |
C424 | 0.0238 (6) | 0.0133 (5) | 0.0203 (6) | 0.0035 (4) | 0.0130 (5) | 0.0063 (4) |
C425 | 0.0217 (6) | 0.0160 (5) | 0.0199 (6) | 0.0088 (4) | 0.0127 (5) | 0.0102 (4) |
C426 | 0.0159 (5) | 0.0163 (5) | 0.0143 (5) | 0.0048 (4) | 0.0082 (4) | 0.0071 (4) |
C427 | 0.0361 (7) | 0.0139 (6) | 0.0301 (7) | 0.0033 (5) | 0.0114 (6) | 0.0052 (5) |
N51 | 0.0180 (5) | 0.0215 (5) | 0.0182 (5) | 0.0086 (4) | 0.0098 (4) | 0.0091 (4) |
O61 | 0.0163 (4) | 0.0187 (4) | 0.0161 (4) | 0.0069 (3) | 0.0044 (3) | 0.0081 (3) |
C61 | 0.0235 (6) | 0.0220 (6) | 0.0156 (6) | 0.0076 (5) | 0.0027 (5) | 0.0096 (5) |
O1 | 0.0219 (4) | 0.0200 (4) | 0.0148 (4) | 0.0052 (3) | 0.0078 (3) | 0.0087 (4) |
N1—C6 | 1.3108 (15) | C47—C47A | 1.3944 (15) |
N1—C2 | 1.3612 (14) | C47—H47 | 0.9500 |
C2—N3 | 1.3425 (14) | C421—C422 | 1.3966 (16) |
C2—N21 | 1.3456 (15) | C421—C426 | 1.3985 (15) |
N3—C4 | 1.3410 (14) | C422—C423 | 1.3884 (16) |
C4—C5 | 1.3723 (16) | C422—H422 | 0.9500 |
C4—N41 | 1.4329 (14) | C423—C424 | 1.3962 (17) |
C5—N51 | 1.4112 (14) | C423—H423 | 0.9500 |
C5—C6 | 1.4178 (15) | C424—C425 | 1.3964 (17) |
C6—O61 | 1.3417 (13) | C424—C427 | 1.5093 (17) |
N21—H21A | 0.920 (16) | C425—C426 | 1.3903 (16) |
N21—H21B | 0.884 (16) | C425—H425 | 0.9500 |
N41—C42 | 1.3860 (14) | C426—H426 | 0.9500 |
N41—C47A | 1.3913 (14) | C427—H47A | 0.9800 |
C42—N43 | 1.3182 (14) | C427—H47B | 0.9800 |
C42—C421 | 1.4694 (15) | C427—H47C | 0.9800 |
N43—C43A | 1.3922 (14) | N51—H51A | 0.908 (16) |
C43A—C44 | 1.4004 (16) | N51—H51B | 0.906 (17) |
C43A—C47A | 1.4007 (15) | O61—C61 | 1.4428 (14) |
C44—C45 | 1.3895 (17) | C61—H61A | 0.9800 |
C44—H44 | 0.9500 | C61—H61B | 0.9800 |
C45—C46 | 1.4038 (17) | C61—H61C | 0.9800 |
C45—H45 | 0.9500 | O1—H1A | 0.872 (18) |
C46—C47 | 1.3873 (16) | O1—H1B | 0.880 (18) |
C46—H46 | 0.9500 | ||
C6—N1—C2 | 116.27 (10) | N41—C47A—C47 | 131.39 (10) |
N3—C2—N21 | 117.55 (10) | N41—C47A—C43A | 105.48 (9) |
N3—C2—N1 | 125.45 (10) | C47—C47A—C43A | 123.10 (10) |
N21—C2—N1 | 116.95 (10) | C422—C421—C426 | 119.22 (10) |
C4—N3—C2 | 115.36 (9) | C422—C421—C42 | 121.38 (10) |
N3—C4—C5 | 125.10 (10) | C426—C421—C42 | 119.38 (10) |
N3—C4—N41 | 115.97 (9) | C423—C422—C421 | 120.15 (11) |
C5—C4—N41 | 118.85 (10) | C423—C422—H422 | 119.9 |
C4—C5—N51 | 125.17 (10) | C421—C422—H422 | 119.9 |
C4—C5—C6 | 113.76 (10) | C422—C423—C424 | 121.21 (11) |
N51—C5—C6 | 120.85 (10) | C422—C423—H423 | 119.4 |
N1—C6—O61 | 121.15 (10) | C424—C423—H423 | 119.4 |
N1—C6—C5 | 123.97 (10) | C423—C424—C425 | 118.19 (11) |
O61—C6—C5 | 114.87 (10) | C423—C424—C427 | 120.61 (11) |
C2—N21—H21A | 117.5 (10) | C425—C424—C427 | 121.20 (11) |
C2—N21—H21B | 119.1 (10) | C426—C425—C424 | 121.21 (11) |
H21A—N21—H21B | 121.0 (14) | C426—C425—H425 | 119.4 |
C42—N41—C47A | 106.59 (9) | C424—C425—H425 | 119.4 |
C42—N41—C4 | 129.12 (9) | C425—C426—C421 | 120.01 (11) |
C47A—N41—C4 | 122.72 (9) | C425—C426—H426 | 120.0 |
N43—C42—N41 | 112.29 (10) | C421—C426—H426 | 120.0 |
N43—C42—C421 | 124.39 (10) | C424—C427—H47A | 109.5 |
N41—C42—C421 | 123.28 (10) | C424—C427—H47B | 109.5 |
C42—N43—C43A | 105.73 (9) | H47A—C427—H47B | 109.5 |
N43—C43A—C44 | 130.53 (10) | C424—C427—H47C | 109.5 |
N43—C43A—C47A | 109.88 (10) | H47A—C427—H47C | 109.5 |
C44—C43A—C47A | 119.58 (10) | H47B—C427—H47C | 109.5 |
C45—C44—C43A | 117.83 (11) | C5—N51—H51A | 112.1 (10) |
C45—C44—H44 | 121.1 | C5—N51—H51B | 114.1 (10) |
C43A—C44—H44 | 121.1 | H51A—N51—H51B | 111.3 (14) |
C44—C45—C46 | 121.60 (11) | C6—O61—C61 | 116.75 (9) |
C44—C45—H45 | 119.2 | O61—C61—H61A | 109.5 |
C46—C45—H45 | 119.2 | O61—C61—H61B | 109.5 |
C47—C46—C45 | 121.37 (11) | H61A—C61—H61B | 109.5 |
C47—C46—H46 | 119.3 | O61—C61—H61C | 109.5 |
C45—C46—H46 | 119.3 | H61A—C61—H61C | 109.5 |
C46—C47—C47A | 116.50 (11) | H61B—C61—H61C | 109.5 |
C46—C47—H47 | 121.8 | H1A—O1—H1B | 105.8 (15) |
C47A—C47—H47 | 121.8 | ||
C6—N1—C2—N3 | 3.53 (16) | C43A—C44—C45—C46 | −0.10 (18) |
C6—N1—C2—N21 | −179.02 (10) | C44—C45—C46—C47 | −0.73 (19) |
N21—C2—N3—C4 | −179.31 (10) | C45—C46—C47—C47A | 0.26 (17) |
N1—C2—N3—C4 | −1.88 (16) | C42—N41—C47A—C47 | −176.73 (12) |
C2—N3—C4—C5 | −1.03 (16) | C4—N41—C47A—C47 | −9.82 (18) |
C2—N3—C4—N41 | 175.46 (9) | C42—N41—C47A—C43A | 1.19 (12) |
N3—C4—C5—N51 | −172.67 (10) | C4—N41—C47A—C43A | 168.09 (10) |
N41—C4—C5—N51 | 10.94 (16) | C46—C47—C47A—N41 | 178.65 (11) |
N3—C4—C5—C6 | 1.92 (16) | C46—C47—C47A—C43A | 1.05 (17) |
N41—C4—C5—C6 | −174.47 (9) | N43—C43A—C47A—N41 | −0.63 (12) |
C2—N1—C6—O61 | 178.12 (9) | C44—C43A—C47A—N41 | 179.98 (10) |
C2—N1—C6—C5 | −2.41 (16) | N43—C43A—C47A—C47 | 177.50 (10) |
C4—C5—C6—N1 | −0.07 (16) | C44—C43A—C47A—C47 | −1.89 (17) |
N51—C5—C6—N1 | 174.78 (10) | N43—C42—C421—C422 | −143.75 (11) |
C4—C5—C6—O61 | 179.43 (9) | N41—C42—C421—C422 | 33.89 (16) |
N51—C5—C6—O61 | −5.72 (15) | N43—C42—C421—C426 | 34.72 (16) |
N3—C4—N41—C42 | 62.21 (15) | N41—C42—C421—C426 | −147.63 (11) |
C5—C4—N41—C42 | −121.08 (12) | C426—C421—C422—C423 | 0.20 (17) |
N3—C4—N41—C47A | −101.53 (12) | C42—C421—C422—C423 | 178.68 (10) |
C5—C4—N41—C47A | 75.18 (14) | C421—C422—C423—C424 | 0.60 (17) |
C47A—N41—C42—N43 | −1.42 (12) | C422—C423—C424—C425 | −0.78 (17) |
C4—N41—C42—N43 | −167.19 (10) | C422—C423—C424—C427 | 178.95 (11) |
C47A—N41—C42—C421 | −179.32 (10) | C423—C424—C425—C426 | 0.18 (17) |
C4—N41—C42—C421 | 14.91 (17) | C427—C424—C425—C426 | −179.56 (11) |
N41—C42—N43—C43A | 1.01 (12) | C424—C425—C426—C421 | 0.61 (17) |
C421—C42—N43—C43A | 178.88 (10) | C422—C421—C426—C425 | −0.80 (16) |
C42—N43—C43A—C44 | 179.09 (12) | C42—C421—C426—C425 | −179.31 (10) |
C42—N43—C43A—C47A | −0.21 (12) | N1—C6—O61—C61 | 0.98 (15) |
N43—C43A—C44—C45 | −177.90 (11) | C5—C6—O61—C61 | −178.54 (9) |
C47A—C43A—C44—C45 | 1.35 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N43 | 0.873 (19) | 1.970 (19) | 2.8421 (15) | 178.1 (17) |
O1—H1B···N51i | 0.880 (19) | 2.08 (2) | 2.9243 (16) | 161.7 (16) |
N21—H21A···O1ii | 0.920 (17) | 2.076 (17) | 2.9881 (16) | 170.7 (14) |
N21—H21B···O1iii | 0.884 (16) | 2.061 (16) | 2.8729 (14) | 152.4 (16) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) x, y, z+1. |
C21H17F3N6O2·C4H8O2 | F(000) = 1104 |
Mr = 530.51 | Dx = 1.363 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.1818 (8) Å | Cell parameters from 6413 reflections |
b = 21.0771 (16) Å | θ = 2.4–28.3° |
c = 13.3610 (11) Å | µ = 0.11 mm−1 |
β = 91.777 (3)° | T = 100 K |
V = 2584.5 (4) Å3 | Block, colourless |
Z = 4 | 0.22 × 0.18 × 0.18 mm |
Bruker D8 Venture diffractometer | 6413 independent reflections |
Radiation source: INCOATEC high brilliance microfocus sealed tube | 5692 reflections with I > 2σ(I) |
Multilayer mirror monochromator | Rint = 0.049 |
φ and ω scans | θmax = 28.3°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −12→12 |
Tmin = 0.919, Tmax = 0.980 | k = −27→28 |
78171 measured reflections | l = −17→17 |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0415P)2 + 2.1776P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
6413 reflections | Δρmax = 0.54 e Å−3 |
372 parameters | Δρmin = −0.44 e Å−3 |
15 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 | Occ. (<1) | |
N1 | 0.70736 (13) | 0.32326 (6) | 0.67797 (9) | 0.0191 (2) | |
C2 | 0.62855 (15) | 0.37693 (7) | 0.67827 (10) | 0.0172 (3) | |
N3 | 0.54458 (13) | 0.39966 (6) | 0.60503 (9) | 0.0169 (2) | |
C4 | 0.54441 (15) | 0.36631 (6) | 0.51893 (10) | 0.0157 (3) | |
C5 | 0.62436 (16) | 0.31175 (7) | 0.50506 (11) | 0.0204 (3) | |
C6 | 0.70376 (16) | 0.29179 (7) | 0.59323 (11) | 0.0208 (3) | |
N21 | 0.63969 (14) | 0.41655 (6) | 0.76410 (9) | 0.0207 (3) | 0.753 (4) |
H21 | 0.6084 | 0.4558 | 0.7573 | 0.025* | 0.753 (4) |
C21 | 0.6938 (9) | 0.39956 (17) | 0.8550 (3) | 0.0312 (7) | 0.753 (4) |
O21 | 0.7528 (3) | 0.34839 (8) | 0.88204 (13) | 0.0397 (6) | 0.753 (4) |
C22 | 0.7133 (8) | 0.4569 (2) | 0.9265 (4) | 0.0303 (5) | 0.753 (4) |
F21 | 0.6081 (10) | 0.5001 (3) | 0.9167 (4) | 0.0409 (7) | 0.753 (4) |
F22 | 0.8364 (11) | 0.4876 (5) | 0.9061 (11) | 0.0583 (6) | 0.753 (4) |
F23 | 0.7217 (13) | 0.4388 (4) | 1.0204 (4) | 0.0597 (14) | 0.753 (4) |
N31 | 0.63969 (14) | 0.41655 (6) | 0.76410 (9) | 0.0207 (3) | 0.247 (4) |
H31 | 0.5996 | 0.4544 | 0.7598 | 0.025* | 0.247 (4) |
C31 | 0.707 (3) | 0.4007 (5) | 0.8513 (9) | 0.0312 (7) | 0.247 (4) |
O31 | 0.6623 (11) | 0.3501 (3) | 0.8895 (4) | 0.0397 (6) | 0.247 (4) |
C32 | 0.724 (3) | 0.4557 (7) | 0.9276 (12) | 0.0303 (5) | 0.247 (4) |
F31 | 0.609 (3) | 0.4938 (10) | 0.9321 (14) | 0.0409 (7) | 0.247 (4) |
F32 | 0.837 (3) | 0.4919 (15) | 0.906 (3) | 0.0583 (6) | 0.247 (4) |
F33 | 0.746 (4) | 0.4327 (14) | 1.0184 (12) | 0.0597 (14) | 0.247 (4) |
N41 | 0.45323 (12) | 0.38991 (5) | 0.43855 (8) | 0.0153 (2) | |
C42 | 0.48539 (15) | 0.43454 (6) | 0.36654 (10) | 0.0150 (3) | |
N43 | 0.37204 (13) | 0.44782 (6) | 0.30671 (9) | 0.0161 (2) | |
C43A | 0.25907 (15) | 0.41008 (6) | 0.34022 (10) | 0.0158 (3) | |
C44 | 0.11293 (16) | 0.40642 (7) | 0.30745 (11) | 0.0193 (3) | |
H44 | 0.0774 | 0.4308 | 0.2520 | 0.023* | |
C45 | 0.02185 (16) | 0.36619 (7) | 0.35840 (12) | 0.0225 (3) | |
H45 | −0.0783 | 0.3640 | 0.3386 | 0.027* | |
C46 | 0.07366 (17) | 0.32850 (7) | 0.43859 (12) | 0.0230 (3) | |
H46 | 0.0086 | 0.3005 | 0.4704 | 0.028* | |
C47 | 0.21845 (16) | 0.33142 (7) | 0.47231 (11) | 0.0198 (3) | |
H47 | 0.2543 | 0.3062 | 0.5266 | 0.024* | |
C47A | 0.30785 (15) | 0.37328 (6) | 0.42236 (10) | 0.0160 (3) | |
C421 | 0.62823 (14) | 0.46485 (6) | 0.35734 (10) | 0.0159 (3) | |
C422 | 0.71016 (15) | 0.48617 (7) | 0.44070 (10) | 0.0167 (3) | |
H422 | 0.6794 | 0.4767 | 0.5063 | 0.020* | |
C423 | 0.83616 (15) | 0.52114 (7) | 0.42784 (11) | 0.0191 (3) | |
H423 | 0.8912 | 0.5353 | 0.4849 | 0.023* | |
C424 | 0.88322 (16) | 0.53592 (7) | 0.33238 (12) | 0.0222 (3) | |
C425 | 0.80315 (17) | 0.51304 (8) | 0.24966 (12) | 0.0241 (3) | |
H425 | 0.8356 | 0.5216 | 0.1842 | 0.029* | |
C426 | 0.67658 (16) | 0.47793 (7) | 0.26146 (11) | 0.0207 (3) | |
H426 | 0.6230 | 0.4629 | 0.2043 | 0.025* | |
C427 | 1.01832 (19) | 0.57542 (9) | 0.32094 (14) | 0.0320 (4) | |
H47A | 1.0209 | 0.5918 | 0.2523 | 0.048* | |
H47B | 1.1047 | 0.5492 | 0.3349 | 0.048* | |
H47C | 1.0173 | 0.6110 | 0.3681 | 0.048* | |
N51 | 0.6318 (2) | 0.27866 (8) | 0.41829 (12) | 0.0403 (4) | |
H51A | 0.586 (3) | 0.2915 (12) | 0.3655 (19) | 0.048* | |
H51B | 0.676 (3) | 0.2407 (12) | 0.4173 (18) | 0.048* | |
O61 | 0.77832 (14) | 0.23785 (6) | 0.58267 (9) | 0.0296 (3) | |
C61 | 0.8521 (2) | 0.21279 (9) | 0.67127 (13) | 0.0361 (4) | |
H61A | 0.7816 | 0.2066 | 0.7239 | 0.054* | |
H61B | 0.9274 | 0.2427 | 0.6946 | 0.054* | |
H61C | 0.8974 | 0.1721 | 0.6553 | 0.054* | |
C71 | 0.3647 (2) | 0.27537 (8) | 0.20733 (13) | 0.0308 (4) | |
C72 | 0.3096 (3) | 0.22030 (10) | 0.26512 (15) | 0.0419 (5) | |
H72A | 0.3763 | 0.2117 | 0.3222 | 0.063* | |
H72B | 0.3038 | 0.1829 | 0.2217 | 0.063* | |
H72C | 0.2126 | 0.2302 | 0.2894 | 0.063* | |
O71 | 0.48004 (15) | 0.30265 (6) | 0.22485 (9) | 0.0356 (3) | |
O72 | 0.27230 (16) | 0.29191 (6) | 0.13288 (10) | 0.0371 (3) | |
C73 | 0.3180 (3) | 0.34448 (9) | 0.07135 (15) | 0.0455 (5) | |
H73A | 0.4026 | 0.3320 | 0.0316 | 0.055* | |
H73B | 0.3463 | 0.3812 | 0.1139 | 0.055* | |
C74 | 0.1899 (3) | 0.36150 (11) | 0.00293 (17) | 0.0568 (7) | |
H74A | 0.1104 | 0.3779 | 0.0428 | 0.085* | |
H74B | 0.1566 | 0.3236 | −0.0337 | 0.085* | |
H74C | 0.2195 | 0.3940 | −0.0448 | 0.085* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0177 (6) | 0.0228 (6) | 0.0168 (6) | −0.0013 (5) | −0.0023 (4) | 0.0026 (5) |
C2 | 0.0163 (6) | 0.0212 (7) | 0.0141 (6) | −0.0043 (5) | 0.0010 (5) | 0.0004 (5) |
N3 | 0.0162 (5) | 0.0189 (6) | 0.0156 (5) | −0.0012 (4) | 0.0009 (4) | −0.0007 (4) |
C4 | 0.0155 (6) | 0.0171 (6) | 0.0143 (6) | 0.0003 (5) | −0.0015 (5) | 0.0011 (5) |
C5 | 0.0228 (7) | 0.0207 (7) | 0.0174 (6) | 0.0050 (5) | −0.0039 (5) | −0.0012 (5) |
C6 | 0.0194 (7) | 0.0220 (7) | 0.0209 (7) | 0.0037 (5) | −0.0030 (5) | 0.0018 (5) |
N21 | 0.0214 (6) | 0.0253 (6) | 0.0154 (6) | −0.0011 (5) | 0.0004 (4) | −0.0028 (5) |
C21 | 0.0562 (19) | 0.0231 (8) | 0.0141 (7) | −0.0171 (8) | −0.0008 (9) | 0.0021 (6) |
O21 | 0.0759 (18) | 0.0198 (7) | 0.0223 (7) | −0.0080 (10) | −0.0170 (11) | 0.0061 (5) |
C22 | 0.0470 (15) | 0.0285 (8) | 0.0152 (7) | −0.0018 (8) | −0.0031 (7) | −0.0018 (6) |
F21 | 0.0589 (8) | 0.0411 (15) | 0.0223 (19) | 0.0097 (11) | −0.0037 (16) | −0.0013 (12) |
F22 | 0.0575 (8) | 0.0537 (16) | 0.0642 (9) | −0.0243 (9) | 0.0080 (7) | −0.0335 (12) |
F23 | 0.122 (5) | 0.0424 (19) | 0.0139 (5) | 0.0191 (16) | −0.0107 (12) | −0.0021 (7) |
N31 | 0.0214 (6) | 0.0253 (6) | 0.0154 (6) | −0.0011 (5) | 0.0004 (4) | −0.0028 (5) |
C31 | 0.0562 (19) | 0.0231 (8) | 0.0141 (7) | −0.0171 (8) | −0.0008 (9) | 0.0021 (6) |
O31 | 0.0759 (18) | 0.0198 (7) | 0.0223 (7) | −0.0080 (10) | −0.0170 (11) | 0.0061 (5) |
C32 | 0.0470 (15) | 0.0285 (8) | 0.0152 (7) | −0.0018 (8) | −0.0031 (7) | −0.0018 (6) |
F31 | 0.0589 (8) | 0.0411 (15) | 0.0223 (19) | 0.0097 (11) | −0.0037 (16) | −0.0013 (12) |
F32 | 0.0575 (8) | 0.0537 (16) | 0.0642 (9) | −0.0243 (9) | 0.0080 (7) | −0.0335 (12) |
F33 | 0.122 (5) | 0.0424 (19) | 0.0139 (5) | 0.0191 (16) | −0.0107 (12) | −0.0021 (7) |
N41 | 0.0151 (5) | 0.0154 (5) | 0.0154 (5) | 0.0018 (4) | −0.0011 (4) | −0.0003 (4) |
C42 | 0.0162 (6) | 0.0150 (6) | 0.0136 (6) | 0.0027 (5) | 0.0004 (5) | −0.0022 (5) |
N43 | 0.0157 (5) | 0.0175 (5) | 0.0150 (5) | 0.0009 (4) | −0.0009 (4) | −0.0017 (4) |
C43A | 0.0173 (6) | 0.0153 (6) | 0.0147 (6) | 0.0011 (5) | −0.0003 (5) | −0.0037 (5) |
C44 | 0.0184 (6) | 0.0225 (7) | 0.0166 (6) | 0.0015 (5) | −0.0038 (5) | −0.0036 (5) |
C45 | 0.0172 (7) | 0.0262 (7) | 0.0240 (7) | −0.0023 (6) | −0.0026 (5) | −0.0082 (6) |
C46 | 0.0224 (7) | 0.0218 (7) | 0.0249 (7) | −0.0067 (6) | 0.0035 (6) | −0.0039 (6) |
C47 | 0.0237 (7) | 0.0167 (6) | 0.0190 (7) | −0.0012 (5) | 0.0002 (5) | −0.0009 (5) |
C47A | 0.0158 (6) | 0.0160 (6) | 0.0161 (6) | 0.0012 (5) | −0.0014 (5) | −0.0035 (5) |
C421 | 0.0138 (6) | 0.0162 (6) | 0.0179 (6) | 0.0028 (5) | 0.0012 (5) | −0.0012 (5) |
C422 | 0.0158 (6) | 0.0178 (6) | 0.0166 (6) | 0.0023 (5) | 0.0019 (5) | −0.0013 (5) |
C423 | 0.0153 (6) | 0.0194 (6) | 0.0225 (7) | 0.0016 (5) | −0.0001 (5) | −0.0041 (5) |
C424 | 0.0171 (7) | 0.0222 (7) | 0.0277 (8) | −0.0002 (5) | 0.0060 (6) | −0.0008 (6) |
C425 | 0.0226 (7) | 0.0299 (8) | 0.0201 (7) | −0.0008 (6) | 0.0066 (6) | 0.0017 (6) |
C426 | 0.0189 (7) | 0.0263 (7) | 0.0168 (6) | 0.0014 (6) | 0.0003 (5) | −0.0017 (5) |
C427 | 0.0255 (8) | 0.0358 (9) | 0.0353 (9) | −0.0103 (7) | 0.0101 (7) | −0.0031 (7) |
N51 | 0.0582 (11) | 0.0382 (9) | 0.0234 (7) | 0.0317 (8) | −0.0162 (7) | −0.0121 (6) |
O61 | 0.0364 (6) | 0.0281 (6) | 0.0239 (6) | 0.0166 (5) | −0.0073 (5) | 0.0007 (5) |
C61 | 0.0407 (10) | 0.0395 (10) | 0.0277 (8) | 0.0212 (8) | −0.0078 (7) | 0.0070 (7) |
C71 | 0.0421 (10) | 0.0271 (8) | 0.0229 (8) | 0.0116 (7) | −0.0023 (7) | −0.0067 (6) |
C72 | 0.0589 (13) | 0.0381 (10) | 0.0284 (9) | 0.0033 (9) | −0.0033 (9) | 0.0017 (8) |
O71 | 0.0401 (7) | 0.0396 (7) | 0.0268 (6) | 0.0104 (6) | −0.0044 (5) | −0.0037 (5) |
O72 | 0.0542 (8) | 0.0284 (6) | 0.0278 (6) | 0.0023 (6) | −0.0131 (6) | −0.0035 (5) |
C73 | 0.0744 (15) | 0.0295 (9) | 0.0317 (10) | 0.0013 (9) | −0.0151 (10) | 0.0016 (8) |
C74 | 0.0933 (19) | 0.0365 (11) | 0.0389 (11) | 0.0125 (12) | −0.0259 (12) | −0.0018 (9) |
N1—C6 | 1.3117 (19) | C47—C47A | 1.390 (2) |
N1—C2 | 1.3429 (19) | C47—H47 | 0.9500 |
C2—N3 | 1.3171 (18) | C421—C426 | 1.396 (2) |
C2—N21 | 1.4196 (18) | C421—C422 | 1.3987 (19) |
N3—C4 | 1.3481 (18) | C422—C423 | 1.387 (2) |
C4—C5 | 1.3800 (19) | C422—H422 | 0.9500 |
C4—N41 | 1.4303 (17) | C423—C424 | 1.394 (2) |
C5—N51 | 1.357 (2) | C423—H423 | 0.9500 |
C5—C6 | 1.4293 (19) | C424—C425 | 1.394 (2) |
C6—O61 | 1.3369 (18) | C424—C427 | 1.506 (2) |
N21—C21 | 1.346 (3) | C425—C426 | 1.391 (2) |
N21—H21 | 0.8800 | C425—H425 | 0.9500 |
C21—O21 | 1.255 (5) | C426—H426 | 0.9500 |
C21—C22 | 1.548 (3) | C427—H47A | 0.9800 |
C22—F23 | 1.312 (3) | C427—H47B | 0.9800 |
C22—F21 | 1.330 (3) | C427—H47C | 0.9800 |
C22—F22 | 1.338 (3) | N51—H51A | 0.86 (3) |
C31—O31 | 1.256 (11) | N51—H51B | 0.90 (3) |
C31—C32 | 1.549 (7) | O61—C61 | 1.4457 (19) |
C32—F33 | 1.316 (7) | C61—H61A | 0.9800 |
C32—F31 | 1.325 (8) | C61—H61B | 0.9800 |
C32—F32 | 1.333 (8) | C61—H61C | 0.9800 |
N41—C42 | 1.3838 (17) | C71—O71 | 1.221 (2) |
N41—C47A | 1.3906 (17) | C71—O72 | 1.334 (2) |
C42—N43 | 1.3225 (17) | C71—C72 | 1.491 (3) |
C42—C421 | 1.4674 (19) | C72—H72A | 0.9800 |
N43—C43A | 1.3922 (18) | C72—H72B | 0.9800 |
C43A—C44 | 1.4007 (19) | C72—H72C | 0.9800 |
C43A—C47A | 1.4057 (19) | O72—C73 | 1.449 (2) |
C44—C45 | 1.385 (2) | C73—C74 | 1.510 (3) |
C44—H44 | 0.9500 | C73—H73A | 0.9900 |
C45—C46 | 1.405 (2) | C73—H73B | 0.9900 |
C45—H45 | 0.9500 | C74—H74A | 0.9800 |
C46—C47 | 1.392 (2) | C74—H74B | 0.9800 |
C46—H46 | 0.9500 | C74—H74C | 0.9800 |
C6—N1—C2 | 115.43 (12) | N41—C47A—C43A | 105.27 (12) |
N3—C2—N1 | 127.38 (13) | C426—C421—C422 | 119.25 (13) |
N3—C2—N21 | 114.34 (13) | C426—C421—C42 | 118.25 (12) |
N1—C2—N21 | 118.20 (12) | C422—C421—C42 | 122.22 (12) |
C2—N3—C4 | 115.44 (12) | C423—C422—C421 | 120.15 (13) |
N3—C4—C5 | 124.23 (13) | C423—C422—H422 | 119.9 |
N3—C4—N41 | 116.40 (12) | C421—C422—H422 | 119.9 |
C5—C4—N41 | 119.37 (12) | C422—C423—C424 | 121.02 (13) |
N51—C5—C4 | 125.75 (14) | C422—C423—H423 | 119.5 |
N51—C5—C6 | 121.02 (14) | C424—C423—H423 | 119.5 |
C4—C5—C6 | 113.23 (13) | C425—C424—C423 | 118.49 (14) |
N1—C6—O61 | 121.46 (13) | C425—C424—C427 | 121.78 (14) |
N1—C6—C5 | 124.13 (13) | C423—C424—C427 | 119.73 (14) |
O61—C6—C5 | 114.39 (13) | C426—C425—C424 | 121.07 (14) |
C21—N21—C2 | 126.0 (2) | C426—C425—H425 | 119.5 |
C21—N21—H21 | 117.0 | C424—C425—H425 | 119.5 |
C2—N21—H21 | 117.0 | C425—C426—C421 | 119.97 (13) |
O21—C21—N21 | 129.2 (4) | C425—C426—H426 | 120.0 |
O21—C21—C22 | 117.0 (3) | C421—C426—H426 | 120.0 |
N21—C21—C22 | 112.4 (3) | C424—C427—H47A | 109.5 |
F23—C22—F21 | 108.3 (3) | C424—C427—H47B | 109.5 |
F23—C22—F22 | 108.1 (4) | H47A—C427—H47B | 109.5 |
F21—C22—F22 | 105.4 (4) | C424—C427—H47C | 109.5 |
F23—C22—C21 | 111.4 (3) | H47A—C427—H47C | 109.5 |
F21—C22—C21 | 113.8 (3) | H47B—C427—H47C | 109.5 |
F22—C22—C21 | 109.5 (4) | C5—N51—H51A | 120.3 (17) |
O31—C31—C32 | 113.3 (12) | C5—N51—H51B | 120.3 (15) |
F33—C32—F31 | 106.4 (11) | H51A—N51—H51B | 119 (2) |
F33—C32—F32 | 108.2 (12) | C6—O61—C61 | 116.93 (13) |
F31—C32—F32 | 107.0 (11) | O61—C61—H61A | 109.5 |
F33—C32—C31 | 109.9 (10) | O61—C61—H61B | 109.5 |
F31—C32—C31 | 114.8 (10) | H61A—C61—H61B | 109.5 |
F32—C32—C31 | 110.3 (11) | O61—C61—H61C | 109.5 |
C42—N41—C47A | 106.72 (11) | H61A—C61—H61C | 109.5 |
C42—N41—C4 | 128.74 (12) | H61B—C61—H61C | 109.5 |
C47A—N41—C4 | 124.46 (12) | O71—C71—O72 | 123.20 (17) |
N43—C42—N41 | 112.54 (12) | O71—C71—C72 | 124.98 (17) |
N43—C42—C421 | 123.08 (12) | O72—C71—C72 | 111.82 (17) |
N41—C42—C421 | 124.38 (12) | C71—C72—H72A | 109.5 |
C42—N43—C43A | 105.35 (11) | C71—C72—H72B | 109.5 |
N43—C43A—C44 | 130.32 (13) | H72A—C72—H72B | 109.5 |
N43—C43A—C47A | 110.11 (12) | C71—C72—H72C | 109.5 |
C44—C43A—C47A | 119.52 (13) | H72A—C72—H72C | 109.5 |
C45—C44—C43A | 117.86 (13) | H72B—C72—H72C | 109.5 |
C45—C44—H44 | 121.1 | C71—O72—C73 | 115.75 (16) |
C43A—C44—H44 | 121.1 | O72—C73—C74 | 106.93 (19) |
C44—C45—C46 | 121.73 (14) | O72—C73—H73A | 110.3 |
C44—C45—H45 | 119.1 | C74—C73—H73A | 110.3 |
C46—C45—H45 | 119.1 | O72—C73—H73B | 110.3 |
C47—C46—C45 | 121.29 (14) | C74—C73—H73B | 110.3 |
C47—C46—H46 | 119.4 | H73A—C73—H73B | 108.6 |
C45—C46—H46 | 119.4 | C73—C74—H74A | 109.5 |
C47A—C47—C46 | 116.43 (13) | C73—C74—H74B | 109.5 |
C47A—C47—H47 | 121.8 | H74A—C74—H74B | 109.5 |
C46—C47—H47 | 121.8 | C73—C74—H74C | 109.5 |
C47—C47A—N41 | 131.59 (13) | H74A—C74—H74C | 109.5 |
C47—C47A—C43A | 123.13 (13) | H74B—C74—H74C | 109.5 |
C6—N1—C2—N3 | 3.0 (2) | C421—C42—N43—C43A | −179.47 (12) |
C6—N1—C2—N21 | −173.61 (13) | C42—N43—C43A—C44 | 177.12 (14) |
N1—C2—N3—C4 | −3.4 (2) | C42—N43—C43A—C47A | −0.15 (15) |
N21—C2—N3—C4 | 173.25 (12) | N43—C43A—C44—C45 | −176.92 (14) |
C2—N3—C4—C5 | 0.3 (2) | C47A—C43A—C44—C45 | 0.1 (2) |
C2—N3—C4—N41 | 179.61 (12) | C43A—C44—C45—C46 | −1.9 (2) |
N3—C4—C5—N51 | −176.87 (17) | C44—C45—C46—C47 | 2.0 (2) |
N41—C4—C5—N51 | 3.8 (2) | C45—C46—C47—C47A | −0.1 (2) |
N3—C4—C5—C6 | 2.7 (2) | C46—C47—C47A—N41 | 176.89 (14) |
N41—C4—C5—C6 | −176.62 (13) | C46—C47—C47A—C43A | −1.7 (2) |
C2—N1—C6—O61 | 179.48 (14) | C42—N41—C47A—C47 | −179.30 (14) |
C2—N1—C6—C5 | 0.7 (2) | C4—N41—C47A—C47 | −2.3 (2) |
N51—C5—C6—N1 | 176.38 (17) | C42—N41—C47A—C43A | −0.54 (14) |
C4—C5—C6—N1 | −3.2 (2) | C4—N41—C47A—C43A | 176.45 (12) |
N51—C5—C6—O61 | −2.5 (2) | N43—C43A—C47A—C47 | 179.33 (13) |
C4—C5—C6—O61 | 177.89 (13) | C44—C43A—C47A—C47 | 1.7 (2) |
N3—C2—N21—C21 | 166.2 (4) | N43—C43A—C47A—N41 | 0.44 (15) |
N1—C2—N21—C21 | −16.8 (5) | C44—C43A—C47A—N41 | −177.17 (12) |
C2—N21—C21—O21 | 4.9 (10) | N43—C42—C421—C426 | −37.18 (19) |
C2—N21—C21—C22 | 170.6 (3) | N41—C42—C421—C426 | 143.65 (14) |
O21—C21—C22—F23 | −32.1 (8) | N43—C42—C421—C422 | 136.72 (14) |
N21—C21—C22—F23 | 160.3 (7) | N41—C42—C421—C422 | −42.5 (2) |
O21—C21—C22—F21 | −154.9 (7) | C426—C421—C422—C423 | 1.5 (2) |
N21—C21—C22—F21 | 37.5 (7) | C42—C421—C422—C423 | −172.37 (13) |
O21—C21—C22—F22 | 87.5 (8) | C421—C422—C423—C424 | 0.3 (2) |
N21—C21—C22—F22 | −80.1 (8) | C422—C423—C424—C425 | −2.0 (2) |
O31—C31—C32—F33 | 26 (2) | C422—C423—C424—C427 | 178.41 (14) |
O31—C31—C32—F31 | −94 (2) | C423—C424—C425—C426 | 2.0 (2) |
O31—C31—C32—F32 | 145 (2) | C427—C424—C425—C426 | −178.39 (15) |
N3—C4—N41—C42 | 87.21 (17) | C424—C425—C426—C421 | −0.3 (2) |
C5—C4—N41—C42 | −93.41 (18) | C422—C421—C426—C425 | −1.5 (2) |
N3—C4—N41—C47A | −89.09 (16) | C42—C421—C426—C425 | 172.63 (13) |
C5—C4—N41—C47A | 90.29 (17) | N1—C6—O61—C61 | 5.5 (2) |
C47A—N41—C42—N43 | 0.49 (15) | C5—C6—O61—C61 | −175.58 (15) |
C4—N41—C42—N43 | −176.33 (12) | O71—C71—O72—C73 | 1.0 (2) |
C47A—N41—C42—C421 | 179.73 (12) | C72—C71—O72—C73 | −178.99 (16) |
C4—N41—C42—C421 | 2.9 (2) | C71—O72—C73—C74 | −171.64 (16) |
N41—C42—N43—C43A | −0.21 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···N43i | 0.88 | 2.21 | 3.0121 (18) | 151 |
N31—H31···N43i | 0.88 | 2.26 | 3.0121 (18) | 143 |
N51—H51A···O71 | 0.85 (3) | 2.10 (3) | 2.942 (2) | 168 (2) |
N51—H51B···O21ii | 0.90 (3) | 2.07 (3) | 2.945 (3) | 166 (2) |
N51—H51B···O31ii | 0.90 (3) | 1.95 (3) | 2.757 (7) | 148 (2) |
C47—H47···O72iii | 0.95 | 2.51 | 3.397 (2) | 155 |
C422—H422···Cg3i | 0.95 | 2.90 | 3.3906 (15) | 113 |
C423—H423···Cg4i | 0.95 | 2.68 | 3.3562 (16) | 129 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z−1/2; (iii) x, −y+1/2, z+1/2. |
C21H17F3N6O2·CH4O | F(000) = 984 |
Mr = 474.45 | Dx = 1.466 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.6296 (8) Å | Cell parameters from 4939 reflections |
b = 11.2206 (7) Å | θ = 2.3–27.5° |
c = 15.648 (1) Å | µ = 0.12 mm−1 |
β = 104.180 (2)° | T = 100 K |
V = 2149.9 (2) Å3 | Block, colourless |
Z = 4 | 0.23 × 0.17 × 0.10 mm |
Bruker D8 Venture diffractometer | 4939 independent reflections |
Radiation source: INCOATEC high brilliance microfocus sealed tube | 4034 reflections with I > 2σ(I) |
Multilayer mirror monochromator | Rint = 0.062 |
φ and ω scans | θmax = 27.5°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −16→16 |
Tmin = 0.906, Tmax = 0.988 | k = −14→14 |
35768 measured reflections | l = −20→20 |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.098 | w = 1/[σ2(Fo2) + (0.0381P)2 + 1.4265P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
4939 reflections | Δρmax = 0.36 e Å−3 |
322 parameters | Δρmin = −0.30 e Å−3 |
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 | ||
N1 | 0.44822 (10) | 0.59122 (10) | 0.56152 (8) | 0.0139 (2) | |
C2 | 0.35695 (12) | 0.55122 (12) | 0.50427 (9) | 0.0134 (3) | |
N3 | 0.29446 (10) | 0.45941 (11) | 0.51707 (8) | 0.0139 (2) | |
C4 | 0.32968 (11) | 0.40147 (12) | 0.59311 (9) | 0.0124 (3) | |
C5 | 0.42117 (12) | 0.43252 (12) | 0.65738 (9) | 0.0129 (3) | |
C6 | 0.47812 (11) | 0.53297 (12) | 0.63687 (9) | 0.0128 (3) | |
N21 | 0.32390 (11) | 0.60912 (12) | 0.42659 (9) | 0.0171 (3) | |
H21A | 0.3703 (15) | 0.6564 (17) | 0.4073 (12) | 0.020* | |
H21B | 0.2750 (16) | 0.5731 (17) | 0.3866 (13) | 0.020* | |
N41 | 0.26399 (10) | 0.30299 (10) | 0.60547 (8) | 0.0132 (2) | |
C42 | 0.29557 (12) | 0.18581 (12) | 0.62382 (10) | 0.0147 (3) | |
N43 | 0.21546 (10) | 0.11940 (11) | 0.63715 (8) | 0.0166 (3) | |
C43A | 0.12565 (12) | 0.19508 (13) | 0.62662 (10) | 0.0155 (3) | |
C44 | 0.01885 (13) | 0.17056 (14) | 0.63136 (11) | 0.0197 (3) | |
H44 | −0.0021 | 0.0927 | 0.6446 | 0.024* | |
C45 | −0.05517 (13) | 0.26339 (15) | 0.61613 (11) | 0.0210 (3) | |
H45 | −0.1284 | 0.2488 | 0.6187 | 0.025* | |
C46 | −0.02464 (13) | 0.37901 (14) | 0.59695 (10) | 0.0187 (3) | |
H46 | −0.0776 | 0.4408 | 0.5872 | 0.022* | |
C47 | 0.08095 (12) | 0.40481 (13) | 0.59187 (10) | 0.0164 (3) | |
H47 | 0.1021 | 0.4828 | 0.5793 | 0.020* | |
C47A | 0.15405 (12) | 0.31017 (13) | 0.60619 (9) | 0.0140 (3) | |
C421 | 0.40413 (12) | 0.13980 (12) | 0.62209 (10) | 0.0142 (3) | |
C422 | 0.45522 (12) | 0.05504 (13) | 0.68408 (10) | 0.0168 (3) | |
H422 | 0.4207 | 0.0286 | 0.7282 | 0.020* | |
C423 | 0.55623 (13) | 0.00967 (13) | 0.68101 (10) | 0.0188 (3) | |
H423 | 0.5911 | −0.0464 | 0.7243 | 0.023* | |
C424 | 0.60792 (12) | 0.04435 (13) | 0.61583 (10) | 0.0180 (3) | |
C425 | 0.55521 (12) | 0.12752 (13) | 0.55353 (10) | 0.0172 (3) | |
H425 | 0.5885 | 0.1516 | 0.5081 | 0.021* | |
C426 | 0.45542 (12) | 0.17567 (13) | 0.55667 (10) | 0.0158 (3) | |
H426 | 0.4216 | 0.2333 | 0.5142 | 0.019* | |
C427 | 0.71716 (13) | −0.00621 (15) | 0.61208 (12) | 0.0240 (4) | |
H42A | 0.7293 | 0.0073 | 0.5534 | 0.036* | |
H42B | 0.7183 | −0.0920 | 0.6241 | 0.036* | |
H42C | 0.7749 | 0.0331 | 0.6564 | 0.036* | |
N51 | 0.45019 (10) | 0.37407 (11) | 0.74001 (8) | 0.0135 (2) | |
H51 | 0.3981 (15) | 0.3683 (15) | 0.7723 (12) | 0.016* | |
C51 | 0.54677 (12) | 0.31925 (12) | 0.76959 (9) | 0.0141 (3) | |
O51 | 0.62094 (8) | 0.31068 (9) | 0.73298 (7) | 0.0169 (2) | |
C52 | 0.55994 (13) | 0.26709 (14) | 0.86307 (10) | 0.0194 (3) | |
F51 | 0.47358 (8) | 0.20306 (9) | 0.86958 (7) | 0.0277 (2) | |
F52 | 0.57112 (11) | 0.35418 (10) | 0.92225 (7) | 0.0396 (3) | |
F53 | 0.64625 (9) | 0.19812 (12) | 0.88476 (8) | 0.0481 (4) | |
O61 | 0.56582 (8) | 0.56787 (9) | 0.69838 (7) | 0.0156 (2) | |
C61 | 0.62461 (13) | 0.66997 (14) | 0.67725 (11) | 0.0200 (3) | |
H61A | 0.6519 | 0.6522 | 0.6252 | 0.030* | |
H61B | 0.6862 | 0.6881 | 0.7272 | 0.030* | |
H61C | 0.5755 | 0.7388 | 0.6650 | 0.030* | |
O71 | 0.27979 (10) | 0.38202 (10) | 0.81511 (8) | 0.0217 (2) | |
H71 | 0.2760 (17) | 0.453 (2) | 0.8345 (14) | 0.033* | |
C71 | 0.23100 (16) | 0.29836 (16) | 0.86160 (13) | 0.0303 (4) | |
H71A | 0.2694 | 0.2994 | 0.9241 | 0.045* | |
H71B | 0.2357 | 0.2185 | 0.8375 | 0.045* | |
H71C | 0.1542 | 0.3194 | 0.8553 | 0.045* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0142 (6) | 0.0126 (6) | 0.0159 (6) | 0.0004 (5) | 0.0060 (5) | 0.0012 (5) |
C2 | 0.0129 (7) | 0.0130 (6) | 0.0156 (7) | 0.0027 (5) | 0.0063 (5) | 0.0000 (5) |
N3 | 0.0146 (6) | 0.0130 (6) | 0.0145 (6) | 0.0006 (5) | 0.0041 (5) | 0.0013 (5) |
C4 | 0.0131 (7) | 0.0103 (6) | 0.0155 (7) | 0.0010 (5) | 0.0066 (5) | −0.0003 (5) |
C5 | 0.0138 (7) | 0.0127 (6) | 0.0129 (7) | 0.0022 (5) | 0.0045 (5) | 0.0004 (5) |
C6 | 0.0123 (7) | 0.0122 (6) | 0.0149 (7) | 0.0011 (5) | 0.0052 (5) | −0.0022 (5) |
N21 | 0.0154 (6) | 0.0195 (6) | 0.0162 (6) | −0.0013 (5) | 0.0034 (5) | 0.0046 (5) |
N41 | 0.0131 (6) | 0.0122 (6) | 0.0143 (6) | −0.0006 (5) | 0.0033 (5) | 0.0011 (4) |
C42 | 0.0189 (7) | 0.0123 (6) | 0.0136 (7) | −0.0017 (6) | 0.0050 (5) | 0.0007 (5) |
N43 | 0.0169 (6) | 0.0152 (6) | 0.0186 (6) | −0.0008 (5) | 0.0061 (5) | 0.0022 (5) |
C43A | 0.0177 (7) | 0.0161 (7) | 0.0131 (7) | −0.0004 (6) | 0.0046 (5) | 0.0003 (5) |
C44 | 0.0198 (8) | 0.0191 (7) | 0.0221 (8) | −0.0043 (6) | 0.0085 (6) | 0.0021 (6) |
C45 | 0.0159 (7) | 0.0264 (8) | 0.0227 (8) | −0.0023 (6) | 0.0083 (6) | 0.0021 (6) |
C46 | 0.0178 (8) | 0.0208 (7) | 0.0186 (7) | 0.0044 (6) | 0.0066 (6) | 0.0013 (6) |
C47 | 0.0188 (8) | 0.0154 (7) | 0.0156 (7) | 0.0008 (6) | 0.0056 (6) | 0.0015 (5) |
C47A | 0.0147 (7) | 0.0164 (7) | 0.0114 (6) | −0.0024 (5) | 0.0041 (5) | −0.0004 (5) |
C421 | 0.0146 (7) | 0.0113 (6) | 0.0165 (7) | −0.0010 (5) | 0.0032 (6) | −0.0013 (5) |
C422 | 0.0195 (8) | 0.0137 (7) | 0.0174 (7) | −0.0014 (6) | 0.0046 (6) | 0.0010 (5) |
C423 | 0.0192 (8) | 0.0147 (7) | 0.0199 (8) | 0.0008 (6) | 0.0000 (6) | 0.0004 (6) |
C424 | 0.0163 (7) | 0.0144 (7) | 0.0219 (8) | −0.0009 (6) | 0.0023 (6) | −0.0056 (6) |
C425 | 0.0180 (7) | 0.0166 (7) | 0.0181 (7) | −0.0024 (6) | 0.0065 (6) | −0.0025 (6) |
C426 | 0.0187 (7) | 0.0129 (6) | 0.0154 (7) | 0.0000 (5) | 0.0037 (6) | 0.0003 (5) |
C427 | 0.0173 (8) | 0.0240 (8) | 0.0297 (9) | 0.0033 (6) | 0.0040 (7) | −0.0040 (7) |
N51 | 0.0156 (6) | 0.0139 (6) | 0.0120 (6) | −0.0003 (5) | 0.0053 (5) | 0.0018 (4) |
C51 | 0.0150 (7) | 0.0138 (6) | 0.0134 (7) | −0.0020 (5) | 0.0032 (5) | −0.0002 (5) |
O51 | 0.0155 (5) | 0.0191 (5) | 0.0174 (5) | −0.0001 (4) | 0.0063 (4) | 0.0013 (4) |
C52 | 0.0167 (7) | 0.0248 (8) | 0.0173 (7) | 0.0016 (6) | 0.0055 (6) | 0.0060 (6) |
F51 | 0.0276 (5) | 0.0310 (5) | 0.0253 (5) | −0.0068 (4) | 0.0079 (4) | 0.0120 (4) |
F52 | 0.0644 (8) | 0.0391 (6) | 0.0141 (5) | −0.0164 (6) | 0.0072 (5) | −0.0021 (4) |
F53 | 0.0329 (6) | 0.0763 (9) | 0.0401 (7) | 0.0320 (6) | 0.0188 (5) | 0.0403 (6) |
O61 | 0.0160 (5) | 0.0153 (5) | 0.0151 (5) | −0.0048 (4) | 0.0029 (4) | 0.0005 (4) |
C61 | 0.0215 (8) | 0.0180 (7) | 0.0202 (8) | −0.0088 (6) | 0.0044 (6) | 0.0001 (6) |
O71 | 0.0263 (6) | 0.0155 (5) | 0.0287 (6) | −0.0006 (5) | 0.0170 (5) | −0.0021 (5) |
C71 | 0.0349 (10) | 0.0234 (8) | 0.0400 (10) | 0.0000 (7) | 0.0233 (8) | 0.0047 (7) |
N1—C6 | 1.3198 (19) | C422—C423 | 1.385 (2) |
N1—C2 | 1.3516 (19) | C422—H422 | 0.9500 |
C2—N3 | 1.3423 (19) | C423—C424 | 1.394 (2) |
C2—N21 | 1.3511 (19) | C423—H423 | 0.9500 |
N3—C4 | 1.3331 (18) | C424—C425 | 1.395 (2) |
C4—C5 | 1.378 (2) | C424—C427 | 1.506 (2) |
C4—N41 | 1.4231 (18) | C425—C426 | 1.383 (2) |
C5—C6 | 1.416 (2) | C425—H425 | 0.9500 |
C5—N51 | 1.4156 (18) | C426—H426 | 0.9500 |
C6—O61 | 1.3357 (17) | C427—H42A | 0.9800 |
N21—H21A | 0.90 (2) | C427—H42B | 0.9800 |
N21—H21B | 0.86 (2) | C427—H42C | 0.9800 |
N41—C42 | 1.3835 (18) | N51—C51 | 1.3431 (19) |
N41—C47A | 1.3937 (19) | N51—H51 | 0.925 (19) |
C42—N43 | 1.3138 (19) | C51—O51 | 1.2156 (18) |
C42—C421 | 1.472 (2) | C51—C52 | 1.546 (2) |
N43—C43A | 1.3940 (19) | C52—F53 | 1.3119 (19) |
C43A—C44 | 1.396 (2) | C52—F52 | 1.330 (2) |
C43A—C47A | 1.398 (2) | C52—F51 | 1.3307 (18) |
C44—C45 | 1.381 (2) | O61—C61 | 1.4468 (17) |
C44—H44 | 0.9500 | C61—H61A | 0.9800 |
C45—C46 | 1.407 (2) | C61—H61B | 0.9800 |
C45—H45 | 0.9500 | C61—H61C | 0.9800 |
C46—C47 | 1.386 (2) | O71—C71 | 1.418 (2) |
C46—H46 | 0.9500 | O71—H71 | 0.86 (2) |
C47—C47A | 1.389 (2) | C71—H71A | 0.9800 |
C47—H47 | 0.9500 | C71—H71B | 0.9800 |
C421—C426 | 1.398 (2) | C71—H71C | 0.9800 |
C421—C422 | 1.398 (2) | ||
C6—N1—C2 | 116.02 (12) | C423—C422—H422 | 120.1 |
N3—C2—N21 | 116.09 (13) | C421—C422—H422 | 120.1 |
N3—C2—N1 | 126.38 (13) | C422—C423—C424 | 121.53 (14) |
N21—C2—N1 | 117.52 (13) | C422—C423—H423 | 119.2 |
C4—N3—C2 | 115.31 (12) | C424—C423—H423 | 119.2 |
N3—C4—C5 | 124.40 (13) | C423—C424—C425 | 117.97 (14) |
N3—C4—N41 | 114.95 (12) | C423—C424—C427 | 121.38 (14) |
C5—C4—N41 | 120.64 (13) | C425—C424—C427 | 120.64 (15) |
C4—C5—C6 | 114.69 (13) | C426—C425—C424 | 121.30 (14) |
C4—C5—N51 | 122.19 (13) | C426—C425—H425 | 119.4 |
C6—C5—N51 | 122.93 (13) | C424—C425—H425 | 119.4 |
N1—C6—O61 | 120.25 (13) | C425—C426—C421 | 120.22 (14) |
N1—C6—C5 | 123.14 (13) | C425—C426—H426 | 119.9 |
O61—C6—C5 | 116.60 (12) | C421—C426—H426 | 119.9 |
C2—N21—H21A | 120.3 (12) | C424—C427—H42A | 109.5 |
C2—N21—H21B | 115.8 (12) | C424—C427—H42B | 109.5 |
H21A—N21—H21B | 116.3 (17) | H42A—C427—H42B | 109.5 |
C42—N41—C47A | 106.88 (12) | C424—C427—H42C | 109.5 |
C42—N41—C4 | 128.18 (12) | H42A—C427—H42C | 109.5 |
C47A—N41—C4 | 124.84 (12) | H42B—C427—H42C | 109.5 |
N43—C42—N41 | 112.21 (13) | C51—N51—C5 | 122.48 (13) |
N43—C42—C421 | 124.14 (13) | C51—N51—H51 | 119.1 (11) |
N41—C42—C421 | 123.51 (13) | C5—N51—H51 | 118.2 (11) |
C42—N43—C43A | 105.77 (12) | O51—C51—N51 | 127.84 (14) |
N43—C43A—C44 | 129.97 (14) | O51—C51—C52 | 119.95 (13) |
N43—C43A—C47A | 110.05 (13) | N51—C51—C52 | 112.18 (13) |
C44—C43A—C47A | 119.96 (14) | F53—C52—F52 | 108.28 (14) |
C45—C44—C43A | 117.66 (14) | F53—C52—F51 | 107.84 (13) |
C45—C44—H44 | 121.2 | F52—C52—F51 | 107.02 (13) |
C43A—C44—H44 | 121.2 | F53—C52—C51 | 110.98 (13) |
C44—C45—C46 | 121.54 (14) | F52—C52—C51 | 110.43 (12) |
C44—C45—H45 | 119.2 | F51—C52—C51 | 112.12 (12) |
C46—C45—H45 | 119.2 | C6—O61—C61 | 116.67 (11) |
C47—C46—C45 | 121.53 (14) | O61—C61—H61A | 109.5 |
C47—C46—H46 | 119.2 | O61—C61—H61B | 109.5 |
C45—C46—H46 | 119.2 | H61A—C61—H61B | 109.5 |
C46—C47—C47A | 116.23 (14) | O61—C61—H61C | 109.5 |
C46—C47—H47 | 121.9 | H61A—C61—H61C | 109.5 |
C47A—C47—H47 | 121.9 | H61B—C61—H61C | 109.5 |
C47—C47A—N41 | 131.85 (13) | C71—O71—H71 | 111.5 (14) |
C47—C47A—C43A | 123.06 (14) | O71—C71—H71A | 109.5 |
N41—C47A—C43A | 105.09 (12) | O71—C71—H71B | 109.5 |
C426—C421—C422 | 119.08 (14) | H71A—C71—H71B | 109.5 |
C426—C421—C42 | 120.89 (13) | O71—C71—H71C | 109.5 |
C422—C421—C42 | 119.97 (13) | H71A—C71—H71C | 109.5 |
C423—C422—C421 | 119.89 (14) | H71B—C71—H71C | 109.5 |
C6—N1—C2—N3 | 0.4 (2) | C42—N41—C47A—C47 | −179.74 (15) |
C6—N1—C2—N21 | 179.81 (13) | C4—N41—C47A—C47 | 3.6 (2) |
N21—C2—N3—C4 | 178.43 (13) | C42—N41—C47A—C43A | 0.87 (15) |
N1—C2—N3—C4 | −2.2 (2) | C4—N41—C47A—C43A | −175.77 (13) |
C2—N3—C4—C5 | 2.1 (2) | N43—C43A—C47A—C47 | 179.92 (13) |
C2—N3—C4—N41 | −178.95 (12) | C44—C43A—C47A—C47 | 1.5 (2) |
N3—C4—C5—C6 | −0.4 (2) | N43—C43A—C47A—N41 | −0.62 (16) |
N41—C4—C5—C6 | −179.30 (12) | C44—C43A—C47A—N41 | −179.02 (13) |
N3—C4—C5—N51 | 174.74 (13) | N43—C42—C421—C426 | 135.26 (16) |
N41—C4—C5—N51 | −4.2 (2) | N41—C42—C421—C426 | −40.1 (2) |
C2—N1—C6—O61 | −178.40 (12) | N43—C42—C421—C422 | −41.9 (2) |
C2—N1—C6—C5 | 1.5 (2) | N41—C42—C421—C422 | 142.77 (15) |
C4—C5—C6—N1 | −1.6 (2) | C426—C421—C422—C423 | 1.2 (2) |
N51—C5—C6—N1 | −176.65 (13) | C42—C421—C422—C423 | 178.42 (13) |
C4—C5—C6—O61 | 178.39 (12) | C421—C422—C423—C424 | −1.6 (2) |
N51—C5—C6—O61 | 3.3 (2) | C422—C423—C424—C425 | 0.5 (2) |
N3—C4—N41—C42 | 124.55 (15) | C422—C423—C424—C427 | −179.30 (14) |
C5—C4—N41—C42 | −56.5 (2) | C423—C424—C425—C426 | 0.9 (2) |
N3—C4—N41—C47A | −59.54 (18) | C427—C424—C425—C426 | −179.31 (14) |
C5—C4—N41—C47A | 119.46 (16) | C424—C425—C426—C421 | −1.2 (2) |
C47A—N41—C42—N43 | −0.87 (17) | C422—C421—C426—C425 | 0.1 (2) |
C4—N41—C42—N43 | 175.62 (13) | C42—C421—C426—C425 | −177.03 (13) |
C47A—N41—C42—C421 | 174.97 (13) | C4—C5—N51—C51 | 121.97 (16) |
C4—N41—C42—C421 | −8.5 (2) | C6—C5—N51—C51 | −63.29 (19) |
N41—C42—N43—C43A | 0.47 (16) | C5—N51—C51—O51 | −0.1 (2) |
C421—C42—N43—C43A | −175.34 (13) | C5—N51—C51—C52 | 177.62 (12) |
C42—N43—C43A—C44 | 178.29 (16) | O51—C51—C52—F53 | −12.2 (2) |
C42—N43—C43A—C47A | 0.11 (16) | N51—C51—C52—F53 | 169.85 (14) |
N43—C43A—C44—C45 | −178.64 (15) | O51—C51—C52—F52 | 107.89 (16) |
C47A—C43A—C44—C45 | −0.6 (2) | N51—C51—C52—F52 | −70.06 (16) |
C43A—C44—C45—C46 | −0.3 (2) | O51—C51—C52—F51 | −132.87 (14) |
C44—C45—C46—C47 | 0.4 (2) | N51—C51—C52—F51 | 49.18 (17) |
C45—C46—C47—C47A | 0.4 (2) | N1—C6—O61—C61 | −0.51 (19) |
C46—C47—C47A—N41 | 179.32 (15) | C5—C6—O61—C61 | 179.54 (12) |
C46—C47—C47A—C43A | −1.4 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21A···O51i | 0.896 (19) | 2.255 (18) | 2.8952 (17) | 128.1 (15) |
N51—H51···O71 | 0.925 (19) | 1.788 (18) | 2.6944 (18) | 166.1 (17) |
O71—H71···N43ii | 0.86 (2) | 1.92 (2) | 2.7640 (17) | 169 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y+1/2, −z+3/2. |
Parameter | φ1 | φ2 | φ3 | φ4 | φ5 | |
(I) | 131.28 (16) | -60.8 (2) | -172.72 (14) | 144.62 (16) | 29.79 (9) | |
(III) | 120.12 (16) | -42.8 (2) | -170.69 (14) | 148.27 (15) | 29.71 (8) | |
(IV) | 125.40 (15) | -99.47 (15) | 99.45 (14) | 56.08 (17) | 26.79 (8) | |
(V) | 62.21 (15) | 34.54 (7) | ||||
(VI) | 87.21 (17) | 40.12 (7) | ||||
(VIIa) | 124.55 (15) | 41.58 (8) | ||||
(VIIb) | 119.8 (3) | 31.96 (8) |
φ1–φ4 represent the torsion angles N3—C4—N41—C42, C4—C5—N51—C57, C5—N51—C57—C51 and N51—C57—C51—C53, respectively, and φ5 represents the dihedral angle between the planes of the imidazole ring and C421–C426 aryl ring. |
Compound | D—H···A | D—H | H···A | D···A | D—H···A |
(I) | N21—H21A···N43i | 0.88 (2) | 2.13 (2) | 2.985 (2) | 162.6 (19) |
N21—H21B···N3ii | 0.90 (2) | 2.18 (2) | 3.079 (2) | 177.4 (16) | |
C424—H424···Cg1iii | 0.95 | 2.67 | 3.336 (2) | 128 | |
(III) | N21–H21A···N43iv | 0.88 (2) | 2.119 (19) | 2.9777 (19) | 165.2 (19) |
N21—H21B···N3ii | 0.88 (2) | 2.25 (2) | 3.1276 (19) | 179 (2) | |
C425—H425···O541v | 0.95 | 2.42 | 3.335 (2) | 167 | |
C423—H423···Cg2vi | 0.95 | 2.73 | 3.6060 (17) | 154 | |
(IV) | N21—H21A···N43vii | 0.88 (2) | 2.14 (2) | 2.9774 (18) | 160.7 (16) |
N21—H21B···O61viii | 0.90 (2) | 2.37 (2) | 3.0595 (16) | 133.1 (16) | |
N51—H51···O441ix | 0.879 (17) | 2.166 (18) | 3.0241 (18) | 165.0 (16) | |
C53—H53···N1x | 0.95 | 2.50 | 3.396 (2) | 157 | |
C422—H422···O541vii | 0.95 | 2.48 | 3.236 (2) | 136 | |
(V) | O1—H1A···N43 | 0.873 (19) | 1.970 (19) | 2.8421 (15) | 178.1 (17) |
O1—H1B···N51ii | 0.880 (19) | 2.08 (2) | 2.9243 (16) | 161.7 (16) | |
N21—H21A···O1ix | 0.920 (17) | 2.076 (17) | 2.9881 (16) | 170.7 (14) | |
N21—H21B···O1xi | 0.884 (16) | 2.061 (16) | 2.8729 (14) | 152.4 (16) | |
(VI) | N21—H21···N43ii | 0.88 | 2.21 | 3.0121 (18) | 151 |
N31—H31···N43ii | 0.88 | 2.26 | 3.0121 (18) | 143 | |
N51—H51A···O71 | 0.85 (3) | 2.10 (3) | 2.942 (2) | 168 (2) | |
N51—H51B···O21v | 0.90 (3) | 2.07 (3) | 2.945 (3) | 166 (2) | |
N51—H51B···O31v | 0.90 (3) | 1.95 (3) | 2.757 (3) | 148 (2) | |
C47—H47···O72xii | 0.95 | 2.51 | 3.397 (2) | 155 | |
C422—H422···Cg3ii | 0.95 | 2.90 | 3.3906 (15) | 113 | |
C423—H423···Cg4ii | 0.95 | 2.68 | 3.3562 (16) | 129 | |
(VIIa) | N21—H21A···O51ii | 0.896 (19) | 2.255 (18) | 2.8952 (17) | 128.1 (15) |
N51—H51···O71 | 0.925 (19) | 1.788 (18) | 2.6944 (18) | 166.1 (17) | |
O71—H71···N43xiii | 0.86 (2) | 1.92 (2) | 2.7640 (17) | 169 (2) | |
(VIIb) | N21—H21A···N43iv | 0.86 (5) | 2.07 (5) | 2.903 (4) | 166 (3) |
N21—H21B···N3xiv | 0.93 (4) | 2.16 (4) | 3.073 (4) | 170 (3) | |
N51—H251···O71 | 0.88 | 1.91 | 2.760 (4) | 163 |
Symmetry codes:
(i) x-1, y, z;
(ii) -x+1, -y+1, -z+1;
(iii) x+1/2, -y+1/2, z+1/2;
(iv) x, y+1, z;
(v) x, -y-1/2, z-1/2;
(vi) x, -y+1/2, z-1/2;
(vii) x+1/2, -y+3/2, z+1/2;
(viii) x+1, y, z;
(ix) -x, -y+1, -z+1;
(x) x-1/2, -y+3/2, z-1/2;
(xi) x, y, z+1;
(xii) x, -y+1/2, z+1/2;
(xiii) -x+1/2, y+1/2, -z+3/2;
(xiv) -x+1, -y+2, -z+1. Cg1–Cg4 epresent the centroids of the N1/C2/N3,C4–C6, C51–C56, N41/C42/N43/C43A/C47A and C43A/C44–C47/C47A rings, respectively. |
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