Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616011062/yf3108sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616011062/yf3108IIIbsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616011062/yf3108VIIsup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616011062/yf3108IIIbsup4.cml |
CCDC references: 1491446; 1491445
For both compounds, data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).
C23H21NO3 | F(000) = 760 |
Mr = 359.41 | Dx = 1.290 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0386 (9) Å | Cell parameters from 4245 reflections |
b = 8.2036 (8) Å | θ = 3.0–27.5° |
c = 25.119 (3) Å | µ = 0.09 mm−1 |
β = 96.385 (10)° | T = 120 K |
V = 1851.0 (3) Å3 | Plate, colourless |
Z = 4 | 0.25 × 0.20 × 0.12 mm |
Bruker D8 Venture diffractometer | 4239 independent reflections |
Radiation source: high brilliance microfocus sealed tube | 2459 reflections with I > 2σ(I) |
Multilayer monochromator | Rint = 0.085 |
φ and ω scans | θmax = 27.5°, θmin = 3.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −11→11 |
Tmin = 0.816, Tmax = 0.990 | k = −10→10 |
27579 measured reflections | l = −32→31 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.0423P)2 + 0.9869P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
4239 reflections | Δρmax = 0.22 e Å−3 |
247 parameters | Δρmin = −0.23 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
N1 | −0.19551 (18) | 0.4041 (2) | 0.43813 (7) | 0.0192 (4) | |
C2 | −0.1631 (2) | 0.4066 (3) | 0.38799 (8) | 0.0186 (5) | |
C3 | −0.0312 (2) | 0.3342 (3) | 0.37123 (8) | 0.0198 (5) | |
C4 | 0.0654 (2) | 0.2610 (3) | 0.41013 (8) | 0.0195 (5) | |
C4A | 0.0340 (2) | 0.2511 (3) | 0.46368 (8) | 0.0199 (5) | |
C5 | 0.1278 (2) | 0.1716 (3) | 0.50443 (8) | 0.0214 (5) | |
H5 | 0.2162 | 0.1202 | 0.4958 | 0.026* | |
C6 | 0.0936 (2) | 0.1676 (3) | 0.55606 (8) | 0.0207 (5) | |
C7 | −0.0385 (2) | 0.2466 (3) | 0.56815 (9) | 0.0217 (5) | |
H7 | −0.0615 | 0.2454 | 0.6041 | 0.026* | |
C8 | −0.1348 (2) | 0.3247 (3) | 0.53011 (8) | 0.0195 (5) | |
C8A | −0.0998 (2) | 0.3271 (3) | 0.47597 (8) | 0.0183 (5) | |
C21 | −0.2708 (2) | 0.4959 (3) | 0.34951 (8) | 0.0209 (5) | |
C22 | −0.2245 (2) | 0.6021 (3) | 0.31125 (8) | 0.0232 (5) | |
H22 | −0.1211 | 0.6162 | 0.3089 | 0.028* | |
C23 | −0.3268 (2) | 0.6871 (3) | 0.27672 (9) | 0.0280 (5) | |
H23 | −0.2934 | 0.7599 | 0.2512 | 0.034* | |
C24 | −0.4772 (3) | 0.6664 (3) | 0.27935 (9) | 0.0309 (6) | |
H24 | −0.5473 | 0.7236 | 0.2553 | 0.037* | |
C25 | −0.5261 (2) | 0.5617 (3) | 0.31717 (9) | 0.0301 (6) | |
H25 | −0.6297 | 0.5476 | 0.3190 | 0.036* | |
C26 | −0.4241 (2) | 0.4778 (3) | 0.35234 (9) | 0.0244 (5) | |
H26 | −0.4582 | 0.4076 | 0.3785 | 0.029* | |
C31 | 0.0016 (2) | 0.3358 (3) | 0.31348 (8) | 0.0228 (5) | |
O31 | 0.11676 (17) | 0.3967 (2) | 0.30221 (6) | 0.0297 (4) | |
C32 | −0.1067 (3) | 0.2543 (3) | 0.27240 (9) | 0.0287 (5) | |
H32A | −0.1131 | 0.3161 | 0.2388 | 0.043* | |
H32B | −0.2050 | 0.2504 | 0.2853 | 0.043* | |
H32C | −0.0729 | 0.1432 | 0.2662 | 0.043* | |
O41 | 0.20487 (15) | 0.20056 (19) | 0.40043 (6) | 0.0235 (4) | |
C41 | 0.2151 (3) | 0.0768 (3) | 0.36407 (8) | 0.0229 (5) | |
O42 | 0.10873 (17) | 0.01788 (19) | 0.33862 (6) | 0.0287 (4) | |
C42 | 0.3742 (2) | 0.0296 (3) | 0.36258 (9) | 0.0317 (6) | |
H42A | 0.4090 | −0.0318 | 0.3951 | 0.048* | |
H42B | 0.4349 | 0.1280 | 0.3607 | 0.048* | |
H42C | 0.3831 | −0.0384 | 0.3310 | 0.048* | |
C61 | 0.1954 (2) | 0.0834 (3) | 0.59909 (9) | 0.0266 (5) | |
H61A | 0.2251 | −0.0228 | 0.5859 | 0.040* | |
H61B | 0.1432 | 0.0678 | 0.6309 | 0.040* | |
H61C | 0.2842 | 0.1506 | 0.6085 | 0.040* | |
C81 | −0.2728 (2) | 0.4104 (3) | 0.54514 (8) | 0.0224 (5) | |
H81A | −0.2617 | 0.4258 | 0.5845 | 0.027* | |
H81B | −0.2772 | 0.5201 | 0.5286 | 0.027* | |
C82 | −0.4189 (2) | 0.3262 (3) | 0.52922 (8) | 0.0249 (5) | |
H82 | −0.5041 | 0.3702 | 0.5430 | 0.030* | |
C83 | −0.4399 (3) | 0.1981 (3) | 0.49821 (10) | 0.0325 (6) | |
H83A | −0.3581 | 0.1497 | 0.4835 | 0.039* | |
H83B | −0.5369 | 0.1536 | 0.4905 | 0.039* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0185 (9) | 0.0177 (9) | 0.0215 (9) | −0.0021 (8) | 0.0026 (7) | −0.0019 (8) |
C2 | 0.0156 (10) | 0.0172 (11) | 0.0234 (11) | −0.0051 (9) | 0.0043 (9) | −0.0009 (9) |
C3 | 0.0180 (11) | 0.0199 (11) | 0.0221 (11) | −0.0025 (9) | 0.0049 (9) | −0.0033 (10) |
C4 | 0.0147 (10) | 0.0201 (11) | 0.0240 (11) | −0.0008 (9) | 0.0030 (9) | −0.0049 (9) |
C4A | 0.0200 (11) | 0.0171 (11) | 0.0227 (11) | −0.0034 (9) | 0.0024 (9) | −0.0036 (9) |
C5 | 0.0154 (10) | 0.0211 (12) | 0.0279 (12) | −0.0023 (9) | 0.0029 (9) | −0.0027 (10) |
C6 | 0.0187 (11) | 0.0202 (12) | 0.0225 (11) | −0.0030 (9) | −0.0015 (9) | −0.0011 (10) |
C7 | 0.0228 (11) | 0.0202 (11) | 0.0224 (11) | −0.0057 (10) | 0.0041 (9) | −0.0011 (9) |
C8 | 0.0170 (10) | 0.0191 (11) | 0.0226 (11) | −0.0039 (9) | 0.0029 (9) | −0.0031 (9) |
C8A | 0.0181 (10) | 0.0153 (11) | 0.0211 (11) | −0.0039 (9) | 0.0009 (9) | −0.0025 (9) |
C21 | 0.0195 (10) | 0.0237 (12) | 0.0200 (11) | −0.0001 (10) | 0.0039 (9) | −0.0056 (10) |
C22 | 0.0186 (11) | 0.0273 (13) | 0.0240 (11) | 0.0000 (10) | 0.0041 (9) | −0.0020 (10) |
C23 | 0.0294 (13) | 0.0318 (13) | 0.0237 (12) | 0.0042 (11) | 0.0066 (10) | 0.0030 (11) |
C24 | 0.0268 (12) | 0.0413 (15) | 0.0235 (12) | 0.0085 (11) | −0.0017 (10) | −0.0001 (11) |
C25 | 0.0164 (11) | 0.0424 (15) | 0.0311 (13) | 0.0013 (10) | 0.0010 (10) | −0.0046 (12) |
C26 | 0.0223 (11) | 0.0269 (13) | 0.0244 (12) | −0.0014 (10) | 0.0047 (9) | −0.0025 (10) |
C31 | 0.0213 (11) | 0.0220 (12) | 0.0259 (12) | 0.0071 (10) | 0.0057 (9) | −0.0007 (10) |
O31 | 0.0231 (8) | 0.0351 (10) | 0.0325 (9) | 0.0014 (8) | 0.0097 (7) | 0.0044 (8) |
C32 | 0.0309 (13) | 0.0324 (14) | 0.0226 (12) | 0.0041 (11) | 0.0027 (10) | −0.0026 (10) |
O41 | 0.0174 (7) | 0.0270 (9) | 0.0267 (8) | 0.0034 (7) | 0.0045 (6) | −0.0046 (7) |
C41 | 0.0290 (12) | 0.0222 (12) | 0.0181 (11) | 0.0042 (10) | 0.0052 (10) | 0.0026 (10) |
O42 | 0.0316 (9) | 0.0264 (9) | 0.0278 (8) | 0.0002 (8) | 0.0026 (7) | −0.0034 (7) |
C42 | 0.0303 (13) | 0.0363 (15) | 0.0300 (13) | 0.0085 (12) | 0.0097 (10) | 0.0008 (11) |
C61 | 0.0247 (12) | 0.0283 (13) | 0.0265 (12) | 0.0012 (10) | 0.0008 (10) | −0.0016 (10) |
C81 | 0.0222 (11) | 0.0253 (12) | 0.0202 (11) | −0.0002 (10) | 0.0046 (9) | −0.0007 (10) |
C82 | 0.0205 (11) | 0.0282 (13) | 0.0267 (12) | 0.0001 (10) | 0.0063 (9) | 0.0047 (11) |
C83 | 0.0223 (12) | 0.0307 (14) | 0.0455 (15) | −0.0050 (11) | 0.0081 (11) | −0.0006 (12) |
N1—C2 | 1.325 (3) | C24—H24 | 0.9500 |
N1—C8A | 1.366 (3) | C25—C26 | 1.387 (3) |
C2—C3 | 1.437 (3) | C25—H25 | 0.9500 |
C2—C21 | 1.487 (3) | C26—H26 | 0.9500 |
C3—C4 | 1.374 (3) | C31—O31 | 1.216 (2) |
C3—C31 | 1.512 (3) | C31—C32 | 1.498 (3) |
C4—O41 | 1.401 (2) | C32—H32A | 0.9800 |
C4—C4A | 1.408 (3) | C32—H32B | 0.9800 |
C4A—C5 | 1.414 (3) | C32—H32C | 0.9800 |
C4A—C8A | 1.425 (3) | O41—C41 | 1.376 (3) |
C5—C6 | 1.367 (3) | C41—O42 | 1.195 (3) |
C5—H5 | 0.9500 | C41—C42 | 1.494 (3) |
C6—C7 | 1.421 (3) | C42—H42A | 0.9800 |
C6—C61 | 1.507 (3) | C42—H42B | 0.9800 |
C7—C8 | 1.377 (3) | C42—H42C | 0.9800 |
C7—H7 | 0.9500 | C61—H61A | 0.9800 |
C8—C8A | 1.430 (3) | C61—H61B | 0.9800 |
C8—C81 | 1.516 (3) | C61—H61C | 0.9800 |
C21—C22 | 1.395 (3) | C81—C82 | 1.504 (3) |
C21—C26 | 1.403 (3) | C81—H81A | 0.9900 |
C22—C23 | 1.384 (3) | C81—H81B | 0.9900 |
C22—H22 | 0.9500 | C82—C83 | 1.309 (3) |
C23—C24 | 1.379 (3) | C82—H82 | 0.9500 |
C23—H23 | 0.9500 | C83—H83A | 0.9500 |
C24—C25 | 1.389 (3) | C83—H83B | 0.9500 |
C2—N1—C8A | 118.61 (18) | C24—C25—H25 | 119.9 |
N1—C2—C3 | 123.42 (19) | C25—C26—C21 | 120.3 (2) |
N1—C2—C21 | 115.32 (18) | C25—C26—H26 | 119.8 |
C3—C2—C21 | 121.22 (18) | C21—C26—H26 | 119.8 |
C4—C3—C2 | 117.03 (18) | O31—C31—C32 | 122.26 (19) |
C4—C3—C31 | 120.64 (18) | O31—C31—C3 | 119.4 (2) |
C2—C3—C31 | 122.33 (19) | C32—C31—C3 | 118.30 (18) |
C3—C4—O41 | 122.93 (18) | C31—C32—H32A | 109.5 |
C3—C4—C4A | 121.71 (19) | C31—C32—H32B | 109.5 |
O41—C4—C4A | 115.24 (18) | H32A—C32—H32B | 109.5 |
C4—C4A—C5 | 123.39 (19) | C31—C32—H32C | 109.5 |
C4—C4A—C8A | 116.59 (19) | H32A—C32—H32C | 109.5 |
C5—C4A—C8A | 120.02 (18) | H32B—C32—H32C | 109.5 |
C6—C5—C4A | 121.2 (2) | C41—O41—C4 | 120.30 (16) |
C6—C5—H5 | 119.4 | O42—C41—O41 | 122.97 (19) |
C4A—C5—H5 | 119.4 | O42—C41—C42 | 126.9 (2) |
C5—C6—C7 | 118.4 (2) | O41—C41—C42 | 110.09 (19) |
C5—C6—C61 | 120.50 (19) | C41—C42—H42A | 109.5 |
C7—C6—C61 | 121.08 (19) | C41—C42—H42B | 109.5 |
C8—C7—C6 | 123.0 (2) | H42A—C42—H42B | 109.5 |
C8—C7—H7 | 118.5 | C41—C42—H42C | 109.5 |
C6—C7—H7 | 118.5 | H42A—C42—H42C | 109.5 |
C7—C8—C8A | 118.48 (19) | H42B—C42—H42C | 109.5 |
C7—C8—C81 | 121.14 (18) | C6—C61—H61A | 109.5 |
C8A—C8—C81 | 120.37 (18) | C6—C61—H61B | 109.5 |
N1—C8A—C4A | 122.58 (18) | H61A—C61—H61B | 109.5 |
N1—C8A—C8 | 118.57 (18) | C6—C61—H61C | 109.5 |
C4A—C8A—C8 | 118.85 (19) | H61A—C61—H61C | 109.5 |
C22—C21—C26 | 118.4 (2) | H61B—C61—H61C | 109.5 |
C22—C21—C2 | 122.01 (18) | C82—C81—C8 | 116.28 (18) |
C26—C21—C2 | 119.60 (19) | C82—C81—H81A | 108.2 |
C23—C22—C21 | 121.0 (2) | C8—C81—H81A | 108.2 |
C23—C22—H22 | 119.5 | C82—C81—H81B | 108.2 |
C21—C22—H22 | 119.5 | C8—C81—H81B | 108.2 |
C24—C23—C22 | 120.1 (2) | H81A—C81—H81B | 107.4 |
C24—C23—H23 | 120.0 | C83—C82—C81 | 126.3 (2) |
C22—C23—H23 | 120.0 | C83—C82—H82 | 116.8 |
C23—C24—C25 | 120.0 (2) | C81—C82—H82 | 116.8 |
C23—C24—H24 | 120.0 | C82—C83—H83A | 120.0 |
C25—C24—H24 | 120.0 | C82—C83—H83B | 120.0 |
C26—C25—C24 | 120.2 (2) | H83A—C83—H83B | 120.0 |
C26—C25—H25 | 119.9 | ||
C8A—N1—C2—C3 | −0.8 (3) | C7—C8—C8A—N1 | 179.77 (19) |
C8A—N1—C2—C21 | −178.65 (18) | C81—C8—C8A—N1 | −1.9 (3) |
N1—C2—C3—C4 | −0.8 (3) | C7—C8—C8A—C4A | −1.0 (3) |
C21—C2—C3—C4 | 176.93 (19) | C81—C8—C8A—C4A | 177.41 (19) |
N1—C2—C3—C31 | 178.7 (2) | N1—C2—C21—C22 | 136.2 (2) |
C21—C2—C3—C31 | −3.5 (3) | C3—C2—C21—C22 | −41.7 (3) |
C2—C3—C4—O41 | −173.28 (18) | N1—C2—C21—C26 | −41.9 (3) |
C31—C3—C4—O41 | 7.2 (3) | C3—C2—C21—C26 | 140.2 (2) |
C2—C3—C4—C4A | 2.6 (3) | C26—C21—C22—C23 | −0.2 (3) |
C31—C3—C4—C4A | −176.9 (2) | C2—C21—C22—C23 | −178.3 (2) |
C3—C4—C4A—C5 | 177.6 (2) | C21—C22—C23—C24 | −0.7 (3) |
O41—C4—C4A—C5 | −6.2 (3) | C22—C23—C24—C25 | 0.9 (4) |
C3—C4—C4A—C8A | −2.7 (3) | C23—C24—C25—C26 | 0.0 (4) |
O41—C4—C4A—C8A | 173.49 (18) | C24—C25—C26—C21 | −1.0 (3) |
C4—C4A—C5—C6 | 178.9 (2) | C22—C21—C26—C25 | 1.1 (3) |
C8A—C4A—C5—C6 | −0.7 (3) | C2—C21—C26—C25 | 179.2 (2) |
C4A—C5—C6—C7 | −0.5 (3) | C4—C3—C31—O31 | −58.0 (3) |
C4A—C5—C6—C61 | −179.6 (2) | C2—C3—C31—O31 | 122.5 (2) |
C5—C6—C7—C8 | 1.0 (3) | C4—C3—C31—C32 | 119.1 (2) |
C61—C6—C7—C8 | −179.9 (2) | C2—C3—C31—C32 | −60.4 (3) |
C6—C7—C8—C8A | −0.3 (3) | C3—C4—O41—C41 | −62.0 (3) |
C6—C7—C8—C81 | −178.66 (19) | C4A—C4—O41—C41 | 121.8 (2) |
C2—N1—C8A—C4A | 0.7 (3) | C4—O41—C41—O42 | 1.6 (3) |
C2—N1—C8A—C8 | 179.89 (19) | C4—O41—C41—C42 | −177.67 (18) |
C4—C4A—C8A—N1 | 1.0 (3) | C7—C8—C81—C82 | −105.9 (2) |
C5—C4A—C8A—N1 | −179.28 (19) | C8A—C8—C81—C82 | 75.8 (3) |
C4—C4A—C8A—C8 | −178.22 (19) | C8—C81—C82—C83 | −9.1 (3) |
C5—C4A—C8A—C8 | 1.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23···O31i | 0.95 | 2.47 | 3.366 (3) | 158 |
C25—H25···O31ii | 0.95 | 2.60 | 3.482 (3) | 155 |
C32—H32A···O42i | 0.98 | 2.56 | 3.527 (3) | 170 |
C61—H61B···O42iii | 0.98 | 2.58 | 3.414 (3) | 143 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) −x, −y, −z+1. |
C19H17NO | F(000) = 1168 |
Mr = 275.33 | Dx = 1.306 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.756 (5) Å | Cell parameters from 3212 reflections |
b = 10.364 (3) Å | θ = 3.4–27.5° |
c = 15.232 (4) Å | µ = 0.08 mm−1 |
β = 92.774 (8)° | T = 120 K |
V = 2799.7 (14) Å3 | Block, colourless |
Z = 8 | 0.32 × 0.25 × 0.16 mm |
Bruker D8 Venture diffractometer | 3211 independent reflections |
Radiation source: high brilliance microfocus sealed tube | 2042 reflections with I > 2σ(I) |
Multilayer monochromator | Rint = 0.076 |
φ and ω scans | θmax = 27.5°, θmin = 3.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −22→23 |
Tmin = 0.912, Tmax = 0.987 | k = −13→13 |
16087 measured reflections | l = −19→19 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.0374P)2 + 3.8913P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
3211 reflections | Δρmax = 0.35 e Å−3 |
192 parameters | Δρmin = −0.27 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.35524 (12) | 0.4701 (2) | 0.09788 (14) | 0.0234 (5) | |
H1A | 0.3096 | 0.4207 | 0.0789 | 0.028* | |
H1B | 0.3959 | 0.4502 | 0.0578 | 0.028* | |
C2 | 0.33840 (12) | 0.6179 (2) | 0.09894 (13) | 0.0199 (4) | |
H2 | 0.3631 | 0.6622 | 0.0496 | 0.024* | |
N3 | 0.37332 (9) | 0.66015 (16) | 0.18562 (11) | 0.0182 (4) | |
C3A | 0.39097 (10) | 0.5546 (2) | 0.23759 (13) | 0.0171 (4) | |
C4 | 0.37897 (11) | 0.7807 (2) | 0.22030 (13) | 0.0181 (4) | |
C5 | 0.40447 (12) | 0.7960 (2) | 0.30645 (13) | 0.0216 (4) | |
H5 | 0.4073 | 0.8811 | 0.3296 | 0.026* | |
C6 | 0.42726 (11) | 0.6906 (2) | 0.36393 (13) | 0.0200 (4) | |
O6 | 0.45365 (9) | 0.70669 (15) | 0.44093 (9) | 0.0275 (4) | |
C6A | 0.41745 (10) | 0.5624 (2) | 0.32476 (12) | 0.0174 (4) | |
C7 | 0.43394 (11) | 0.4444 (2) | 0.36742 (13) | 0.0189 (4) | |
H7 | 0.4528 | 0.4452 | 0.4269 | 0.023* | |
C8 | 0.42334 (11) | 0.3272 (2) | 0.32467 (13) | 0.0194 (4) | |
C9 | 0.39523 (11) | 0.3250 (2) | 0.23566 (13) | 0.0195 (4) | |
H9 | 0.3873 | 0.2449 | 0.2064 | 0.023* | |
C9A | 0.37961 (11) | 0.4384 (2) | 0.19205 (13) | 0.0188 (4) | |
C21 | 0.25443 (12) | 0.6450 (2) | 0.09482 (15) | 0.0264 (5) | |
H21A | 0.2310 | 0.6003 | 0.1432 | 0.040* | |
H21B | 0.2320 | 0.6141 | 0.0386 | 0.040* | |
H21C | 0.2460 | 0.7381 | 0.0999 | 0.040* | |
C41 | 0.36044 (11) | 0.8936 (2) | 0.16205 (13) | 0.0186 (4) | |
C42 | 0.29734 (12) | 0.9699 (2) | 0.17538 (15) | 0.0237 (5) | |
H42 | 0.2648 | 0.9490 | 0.2209 | 0.028* | |
C43 | 0.28190 (12) | 1.0771 (2) | 0.12198 (15) | 0.0266 (5) | |
H43 | 0.2384 | 1.1281 | 0.1306 | 0.032* | |
C44 | 0.33008 (12) | 1.1088 (2) | 0.05644 (14) | 0.0234 (5) | |
H44 | 0.3201 | 1.1825 | 0.0206 | 0.028* | |
C45 | 0.39300 (11) | 1.0327 (2) | 0.04308 (13) | 0.0209 (4) | |
H45 | 0.4260 | 1.0547 | −0.0019 | 0.025* | |
C46 | 0.40787 (11) | 0.9251 (2) | 0.09485 (13) | 0.0195 (4) | |
H46 | 0.4504 | 0.8726 | 0.0846 | 0.023* | |
C81 | 0.44411 (12) | 0.2013 (2) | 0.36924 (14) | 0.0242 (5) | |
H81A | 0.4748 | 0.2186 | 0.4231 | 0.036* | |
H81B | 0.4729 | 0.1481 | 0.3296 | 0.036* | |
H81C | 0.3981 | 0.1556 | 0.3840 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0271 (11) | 0.0223 (11) | 0.0204 (10) | 0.0002 (9) | −0.0027 (8) | −0.0046 (9) |
C2 | 0.0253 (10) | 0.0210 (10) | 0.0132 (9) | −0.0037 (8) | −0.0026 (8) | −0.0016 (8) |
N3 | 0.0189 (8) | 0.0207 (9) | 0.0150 (8) | −0.0020 (7) | −0.0002 (6) | −0.0025 (7) |
C3A | 0.0135 (9) | 0.0210 (10) | 0.0170 (9) | −0.0005 (8) | 0.0020 (7) | 0.0004 (8) |
C4 | 0.0162 (9) | 0.0192 (10) | 0.0191 (10) | −0.0041 (8) | 0.0034 (7) | −0.0013 (8) |
C5 | 0.0250 (11) | 0.0193 (10) | 0.0207 (10) | −0.0057 (8) | 0.0038 (8) | −0.0048 (8) |
C6 | 0.0204 (10) | 0.0231 (11) | 0.0167 (10) | −0.0064 (8) | 0.0028 (8) | −0.0023 (8) |
O6 | 0.0385 (9) | 0.0271 (8) | 0.0164 (7) | −0.0073 (7) | −0.0036 (6) | −0.0038 (6) |
C6A | 0.0143 (9) | 0.0218 (10) | 0.0162 (9) | −0.0025 (8) | 0.0022 (7) | −0.0023 (8) |
C7 | 0.0143 (9) | 0.0273 (11) | 0.0153 (9) | −0.0018 (8) | 0.0007 (7) | −0.0016 (9) |
C8 | 0.0150 (9) | 0.0220 (11) | 0.0213 (10) | 0.0009 (8) | 0.0022 (8) | 0.0022 (8) |
C9 | 0.0179 (10) | 0.0199 (10) | 0.0207 (10) | 0.0000 (8) | 0.0001 (8) | −0.0059 (8) |
C9A | 0.0163 (9) | 0.0234 (10) | 0.0167 (9) | −0.0004 (8) | −0.0002 (7) | −0.0037 (8) |
C21 | 0.0256 (11) | 0.0232 (11) | 0.0295 (12) | −0.0013 (9) | −0.0081 (9) | −0.0009 (9) |
C41 | 0.0188 (10) | 0.0185 (10) | 0.0184 (10) | −0.0042 (8) | −0.0009 (8) | −0.0025 (8) |
C42 | 0.0224 (11) | 0.0229 (11) | 0.0263 (11) | −0.0032 (8) | 0.0066 (8) | −0.0040 (9) |
C43 | 0.0210 (10) | 0.0229 (12) | 0.0357 (12) | 0.0026 (8) | −0.0004 (9) | −0.0071 (10) |
C44 | 0.0247 (10) | 0.0169 (10) | 0.0280 (11) | −0.0024 (8) | −0.0061 (8) | −0.0023 (9) |
C45 | 0.0209 (10) | 0.0223 (11) | 0.0195 (10) | −0.0060 (8) | 0.0001 (8) | −0.0019 (8) |
C46 | 0.0170 (9) | 0.0215 (11) | 0.0199 (10) | −0.0024 (8) | 0.0013 (8) | −0.0026 (8) |
C81 | 0.0245 (11) | 0.0239 (11) | 0.0240 (11) | 0.0004 (9) | −0.0018 (9) | 0.0013 (9) |
C1—C9A | 1.514 (3) | C8—C81 | 1.508 (3) |
C1—C2 | 1.561 (3) | C9—C9A | 1.372 (3) |
C1—H1A | 0.9900 | C9—H9 | 0.9500 |
C1—H1B | 0.9900 | C21—H21A | 0.9800 |
C2—N3 | 1.497 (2) | C21—H21B | 0.9800 |
C2—C21 | 1.515 (3) | C21—H21C | 0.9800 |
C2—H2 | 1.0000 | C41—C42 | 1.394 (3) |
N3—C4 | 1.358 (3) | C41—C46 | 1.395 (3) |
N3—C3A | 1.377 (3) | C42—C43 | 1.396 (3) |
C3A—C6A | 1.389 (3) | C42—H42 | 0.9500 |
C3A—C9A | 1.399 (3) | C43—C44 | 1.385 (3) |
C4—C5 | 1.376 (3) | C43—H43 | 0.9500 |
C4—C41 | 1.496 (3) | C44—C45 | 1.391 (3) |
C5—C6 | 1.446 (3) | C44—H44 | 0.9500 |
C5—H5 | 0.9500 | C45—C46 | 1.384 (3) |
C6—O6 | 1.253 (2) | C45—H45 | 0.9500 |
C6—C6A | 1.463 (3) | C46—H46 | 0.9500 |
C6A—C7 | 1.409 (3) | C81—H81A | 0.9800 |
C7—C8 | 1.387 (3) | C81—H81B | 0.9800 |
C7—H7 | 0.9500 | C81—H81C | 0.9800 |
C8—C9 | 1.422 (3) | ||
C9A—C1—C2 | 104.42 (16) | C9A—C9—C8 | 120.09 (19) |
C9A—C1—H1A | 110.9 | C9A—C9—H9 | 120.0 |
C2—C1—H1A | 110.9 | C8—C9—H9 | 120.0 |
C9A—C1—H1B | 110.9 | C9—C9A—C3A | 118.44 (18) |
C2—C1—H1B | 110.9 | C9—C9A—C1 | 133.33 (19) |
H1A—C1—H1B | 108.9 | C3A—C9A—C1 | 108.12 (18) |
N3—C2—C21 | 110.32 (17) | C2—C21—H21A | 109.5 |
N3—C2—C1 | 102.98 (16) | C2—C21—H21B | 109.5 |
C21—C2—C1 | 111.70 (17) | H21A—C21—H21B | 109.5 |
N3—C2—H2 | 110.5 | C2—C21—H21C | 109.5 |
C21—C2—H2 | 110.5 | H21A—C21—H21C | 109.5 |
C1—C2—H2 | 110.5 | H21B—C21—H21C | 109.5 |
C4—N3—C3A | 119.76 (17) | C42—C41—C46 | 119.5 (2) |
C4—N3—C2 | 129.18 (17) | C42—C41—C4 | 120.85 (18) |
C3A—N3—C2 | 110.36 (16) | C46—C41—C4 | 119.65 (18) |
N3—C3A—C6A | 124.07 (19) | C41—C42—C43 | 120.2 (2) |
N3—C3A—C9A | 112.03 (17) | C41—C42—H42 | 119.9 |
C6A—C3A—C9A | 123.9 (2) | C43—C42—H42 | 119.9 |
N3—C4—C5 | 119.45 (19) | C44—C43—C42 | 119.9 (2) |
N3—C4—C41 | 118.63 (18) | C44—C43—H43 | 120.1 |
C5—C4—C41 | 121.86 (19) | C42—C43—H43 | 120.1 |
C4—C5—C6 | 124.03 (19) | C43—C44—C45 | 120.0 (2) |
C4—C5—H5 | 118.0 | C43—C44—H44 | 120.0 |
C6—C5—H5 | 118.0 | C45—C44—H44 | 120.0 |
O6—C6—C5 | 123.16 (19) | C46—C45—C44 | 120.40 (19) |
O6—C6—C6A | 122.3 (2) | C46—C45—H45 | 119.8 |
C5—C6—C6A | 114.52 (18) | C44—C45—H45 | 119.8 |
C3A—C6A—C7 | 116.33 (19) | C45—C46—C41 | 120.08 (19) |
C3A—C6A—C6 | 118.07 (19) | C45—C46—H46 | 120.0 |
C7—C6A—C6 | 125.58 (18) | C41—C46—H46 | 120.0 |
C8—C7—C6A | 121.55 (18) | C8—C81—H81A | 109.5 |
C8—C7—H7 | 119.2 | C8—C81—H81B | 109.5 |
C6A—C7—H7 | 119.2 | H81A—C81—H81B | 109.5 |
C7—C8—C9 | 119.67 (19) | C8—C81—H81C | 109.5 |
C7—C8—C81 | 121.44 (19) | H81A—C81—H81C | 109.5 |
C9—C8—C81 | 118.83 (19) | H81B—C81—H81C | 109.5 |
C9A—C1—C2—N3 | 14.0 (2) | C3A—C6A—C7—C8 | −0.7 (3) |
C9A—C1—C2—C21 | −104.33 (19) | C6—C6A—C7—C8 | −179.5 (2) |
C21—C2—N3—C4 | −63.9 (3) | C6A—C7—C8—C9 | 0.0 (3) |
C1—C2—N3—C4 | 176.72 (19) | C6A—C7—C8—C81 | 177.38 (19) |
C21—C2—N3—C3A | 106.25 (19) | C7—C8—C9—C9A | 0.8 (3) |
C1—C2—N3—C3A | −13.1 (2) | C81—C8—C9—C9A | −176.60 (19) |
C4—N3—C3A—C6A | −2.4 (3) | C8—C9—C9A—C3A | −0.9 (3) |
C2—N3—C3A—C6A | −173.63 (18) | C8—C9—C9A—C1 | 174.8 (2) |
C4—N3—C3A—C9A | 178.04 (18) | N3—C3A—C9A—C9 | 179.74 (18) |
C2—N3—C3A—C9A | 6.8 (2) | C6A—C3A—C9A—C9 | 0.2 (3) |
C3A—N3—C4—C5 | 1.9 (3) | N3—C3A—C9A—C1 | 3.0 (2) |
C2—N3—C4—C5 | 171.31 (19) | C6A—C3A—C9A—C1 | −176.54 (18) |
C3A—N3—C4—C41 | 179.19 (17) | C2—C1—C9A—C9 | 173.1 (2) |
C2—N3—C4—C41 | −11.4 (3) | C2—C1—C9A—C3A | −10.9 (2) |
N3—C4—C5—C6 | 0.9 (3) | N3—C4—C41—C42 | 112.5 (2) |
C41—C4—C5—C6 | −176.29 (19) | C5—C4—C41—C42 | −70.3 (3) |
C4—C5—C6—O6 | 176.6 (2) | N3—C4—C41—C46 | −69.1 (2) |
C4—C5—C6—C6A | −3.1 (3) | C5—C4—C41—C46 | 108.1 (2) |
N3—C3A—C6A—C7 | −178.87 (18) | C46—C41—C42—C43 | −0.1 (3) |
C9A—C3A—C6A—C7 | 0.6 (3) | C4—C41—C42—C43 | 178.28 (19) |
N3—C3A—C6A—C6 | 0.0 (3) | C41—C42—C43—C44 | −1.0 (3) |
C9A—C3A—C6A—C6 | 179.51 (18) | C42—C43—C44—C45 | 1.0 (3) |
O6—C6—C6A—C3A | −177.11 (19) | C43—C44—C45—C46 | 0.1 (3) |
C5—C6—C6A—C3A | 2.6 (3) | C44—C45—C46—C41 | −1.2 (3) |
O6—C6—C6A—C7 | 1.6 (3) | C42—C41—C46—C45 | 1.2 (3) |
C5—C6—C6A—C7 | −178.69 (19) | C4—C41—C46—C45 | −177.19 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C46—H46···O6i | 0.95 | 2.46 | 3.405 (3) | 171 |
Symmetry code: (i) −x+1, y, −z+1/2. |