Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S205322962000813X/yf3205sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322962000813X/yf3205compound_I_AAG10sup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322962000813X/yf3205compound_I_AAG10sup8.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322962000813X/yf3205compound_II_AAG9sup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322962000813X/yf3205compound_II_AAG9sup9.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322962000813X/yf3205compound_III_AAG1sup4.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322962000813X/yf3205compound_III_AAG1sup10.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322962000813X/yf3205compound_IV_AAG2sup11.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322962000813X/yf3205compound_IV_AAG2sup5.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322962000813X/yf3205compound_V_AAG5sup12.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322962000813X/yf3205compound_V_AAG5sup6.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S205322962000813X/yf3205AAG4sup13.cml | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322962000813X/yf3205AAG4sup7.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S205322962000813X/yf3205sup14.pdf |
CCDC references: 2010679; 2010678; 2010677; 2010676; 2010675; 2010674
Data collection: CrysAlis PRO (Rigaku OD, 2015) for compound_I_AAG10, compound_II_AAG9, compound_III_AAG1, compound_V_AAG5; CrysAlis PRO (Agilent, 2013) for compound_IV_AAG2; CrysAlis PRO (Rigaku OD, 2019) for AAG4. Cell refinement: CrysAlis PRO (Rigaku OD, 2015) for compound_I_AAG10, compound_II_AAG9, compound_III_AAG1, compound_V_AAG5; CrysAlis PRO (Agilent, 2013) for compound_IV_AAG2; CrysAlis PRO (Rigaku OD, 2019) for AAG4. Data reduction: CrysAlis PRO (Rigaku OD, 2015) for compound_I_AAG10, compound_II_AAG9, compound_III_AAG1, compound_V_AAG5; CrysAlis PRO (Agilent, 2013) for compound_IV_AAG2; CrysAlis PRO (Rigaku OD, 2019) for AAG4. For all structures, program(s) used to solve structure: SHELXS (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 1999); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) and publCIF (Westrip, 2010).
C22H16O2 | F(000) = 1312 |
Mr = 312.35 | Dx = 1.278 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.2487 (3) Å | Cell parameters from 7518 reflections |
b = 16.3033 (4) Å | θ = 3.4–35.7° |
c = 19.7539 (7) Å | µ = 0.08 mm−1 |
β = 100.420 (3)° | T = 100 K |
V = 3246.20 (17) Å3 | Plate, colorless |
Z = 8 | 0.28 × 0.26 × 0.08 mm |
Rigaku OD SuperNova Dual source diffractometer with an Atlas detector | 13340 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source | 11168 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.042 |
Detector resolution: 10.4498 pixels mm-1 | θmax = 26.5°, θmin = 3.3° |
ω scans | h = −12→9 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −20→20 |
Tmin = 0.744, Tmax = 1.000 | l = −24→24 |
13340 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.060 | H-atom parameters constrained |
wR(F2) = 0.153 | w = 1/[σ2(Fo2) + (0.060P)2 + 1.5246P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
13340 reflections | Δρmax = 0.49 e Å−3 |
205 parameters | Δρmin = −0.38 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. |
Refinement. Refined as a 2-component perfect twin. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.32317 (14) | 0.18634 (9) | 0.46640 (7) | 0.0255 (4) | |
O4 | 0.17916 (15) | 0.30418 (10) | 0.28534 (9) | 0.0375 (4) | |
C2 | 0.2187 (2) | 0.14416 (13) | 0.41919 (11) | 0.0226 (4) | |
H2 | 0.1530 | 0.1238 | 0.4471 | 0.027* | |
C3 | 0.14523 (19) | 0.20038 (12) | 0.36501 (11) | 0.0220 (4) | |
C4 | 0.2246 (2) | 0.26304 (13) | 0.33592 (11) | 0.0248 (5) | |
C5 | 0.4459 (2) | 0.33109 (14) | 0.34907 (13) | 0.0320 (5) | |
H5 | 0.4200 | 0.3550 | 0.3048 | 0.038* | |
C6 | 0.5669 (2) | 0.35083 (15) | 0.38841 (14) | 0.0377 (6) | |
H6 | 0.6254 | 0.3871 | 0.3709 | 0.045* | |
C7 | 0.6030 (2) | 0.31731 (14) | 0.45384 (14) | 0.0350 (6) | |
H7 | 0.6850 | 0.3325 | 0.4816 | 0.042* | |
C8 | 0.5213 (2) | 0.26219 (13) | 0.47898 (12) | 0.0288 (5) | |
H8 | 0.5471 | 0.2394 | 0.5237 | 0.035* | |
C9 | 0.40053 (19) | 0.24013 (12) | 0.43838 (11) | 0.0225 (4) | |
C10 | 0.36040 (19) | 0.27579 (13) | 0.37392 (11) | 0.0241 (5) | |
C11 | 0.01360 (19) | 0.19908 (13) | 0.34047 (11) | 0.0249 (5) | |
H11 | −0.0155 | 0.2393 | 0.3063 | 0.030* | |
C12 | −0.09296 (11) | 0.14678 (8) | 0.35704 (8) | 0.0276 (5) | |
C13 | −0.07390 (11) | 0.06755 (9) | 0.38294 (8) | 0.0342 (6) | |
H13 | 0.0124 | 0.0441 | 0.3909 | 0.041* | |
C14 | −0.18105 (15) | 0.02267 (8) | 0.39717 (9) | 0.0425 (6) | |
H14 | −0.1680 | −0.0315 | 0.4149 | 0.051* | |
C15 | −0.30727 (12) | 0.05701 (10) | 0.38550 (9) | 0.0448 (7) | |
H15 | −0.3805 | 0.0263 | 0.3952 | 0.054* | |
C16 | −0.32633 (10) | 0.13624 (10) | 0.35960 (8) | 0.0412 (6) | |
H16 | −0.4126 | 0.1597 | 0.3516 | 0.049* | |
C17 | −0.21918 (13) | 0.18112 (8) | 0.34537 (8) | 0.0334 (5) | |
H17 | −0.2322 | 0.2353 | 0.3277 | 0.040* | |
C18 | 0.27922 (18) | 0.06873 (12) | 0.39076 (11) | 0.0213 (4) | |
C19 | 0.34181 (19) | 0.01096 (13) | 0.43743 (12) | 0.0265 (5) | |
H19 | 0.3452 | 0.0193 | 0.4853 | 0.032* | |
C20 | 0.3992 (2) | −0.05840 (13) | 0.41512 (13) | 0.0311 (5) | |
H20 | 0.4422 | −0.0970 | 0.4477 | 0.037* | |
C21 | 0.3943 (2) | −0.07174 (13) | 0.34587 (13) | 0.0327 (5) | |
H21 | 0.4342 | −0.1192 | 0.3305 | 0.039* | |
C22 | 0.3308 (2) | −0.01541 (15) | 0.29893 (13) | 0.0362 (6) | |
H22 | 0.3261 | −0.0244 | 0.2510 | 0.043* | |
C23 | 0.2737 (2) | 0.05466 (14) | 0.32169 (12) | 0.0302 (5) | |
H23 | 0.2304 | 0.0931 | 0.2890 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0270 (8) | 0.0262 (8) | 0.0219 (8) | −0.0036 (6) | 0.0005 (6) | −0.0032 (6) |
O4 | 0.0286 (8) | 0.0346 (9) | 0.0432 (10) | −0.0068 (7) | −0.0099 (7) | 0.0148 (8) |
C2 | 0.0199 (10) | 0.0250 (11) | 0.0225 (10) | −0.0053 (8) | 0.0021 (8) | −0.0006 (8) |
C3 | 0.0184 (10) | 0.0196 (10) | 0.0278 (11) | 0.0000 (8) | 0.0032 (8) | −0.0022 (8) |
C4 | 0.0195 (10) | 0.0221 (10) | 0.0310 (12) | 0.0009 (8) | −0.0003 (8) | 0.0019 (9) |
C5 | 0.0240 (11) | 0.0291 (12) | 0.0409 (14) | −0.0027 (9) | 0.0006 (10) | 0.0078 (10) |
C6 | 0.0216 (11) | 0.0318 (13) | 0.0575 (17) | −0.0062 (10) | 0.0013 (11) | 0.0059 (11) |
C7 | 0.0211 (11) | 0.0277 (12) | 0.0512 (15) | −0.0014 (9) | −0.0066 (10) | −0.0053 (10) |
C8 | 0.0283 (11) | 0.0240 (11) | 0.0307 (12) | 0.0019 (9) | −0.0038 (9) | −0.0056 (9) |
C9 | 0.0198 (10) | 0.0193 (10) | 0.0279 (11) | 0.0023 (8) | 0.0029 (8) | −0.0040 (8) |
C10 | 0.0161 (10) | 0.0232 (10) | 0.0317 (12) | 0.0005 (8) | 0.0008 (8) | 0.0000 (8) |
C11 | 0.0202 (10) | 0.0246 (11) | 0.0296 (11) | 0.0000 (8) | 0.0037 (9) | −0.0057 (8) |
C12 | 0.0215 (11) | 0.0351 (12) | 0.0263 (11) | −0.0077 (9) | 0.0044 (9) | −0.0101 (9) |
C13 | 0.0268 (12) | 0.0421 (14) | 0.0351 (13) | −0.0108 (10) | 0.0092 (10) | −0.0098 (10) |
C14 | 0.0501 (16) | 0.0438 (15) | 0.0362 (14) | −0.0207 (12) | 0.0143 (12) | −0.0061 (11) |
C15 | 0.0267 (13) | 0.075 (2) | 0.0351 (14) | −0.0264 (13) | 0.0111 (11) | −0.0146 (13) |
C16 | 0.0232 (12) | 0.0681 (19) | 0.0325 (14) | −0.0093 (11) | 0.0056 (10) | −0.0099 (12) |
C17 | 0.0228 (11) | 0.0497 (15) | 0.0279 (12) | −0.0037 (10) | 0.0049 (9) | −0.0109 (10) |
C18 | 0.0162 (9) | 0.0191 (10) | 0.0276 (11) | −0.0041 (8) | 0.0014 (8) | 0.0025 (8) |
C19 | 0.0202 (10) | 0.0285 (11) | 0.0286 (12) | −0.0037 (8) | −0.0012 (8) | 0.0054 (9) |
C20 | 0.0194 (10) | 0.0219 (11) | 0.0470 (14) | −0.0029 (9) | −0.0073 (9) | 0.0093 (10) |
C21 | 0.0231 (11) | 0.0193 (11) | 0.0528 (16) | −0.0017 (9) | −0.0011 (10) | −0.0071 (10) |
C22 | 0.0438 (14) | 0.0321 (13) | 0.0307 (13) | 0.0033 (11) | 0.0016 (11) | −0.0072 (10) |
C23 | 0.0354 (12) | 0.0238 (11) | 0.0291 (12) | 0.0059 (9) | 0.0000 (9) | 0.0036 (9) |
O1—C9 | 1.365 (2) | C12—C17 | 1.3900 |
O1—C2 | 1.459 (2) | C13—C14 | 1.3900 |
O4—C4 | 1.223 (3) | C13—H13 | 0.9500 |
C2—C3 | 1.504 (3) | C14—C15 | 1.3900 |
C2—C18 | 1.529 (3) | C14—H14 | 0.9500 |
C2—H2 | 1.0000 | C15—C16 | 1.3900 |
C3—C11 | 1.349 (3) | C15—H15 | 0.9500 |
C3—C4 | 1.485 (3) | C16—C17 | 1.3900 |
C4—C10 | 1.472 (3) | C16—H16 | 0.9500 |
C5—C6 | 1.378 (3) | C17—H17 | 0.9500 |
C5—C10 | 1.406 (3) | C18—C23 | 1.375 (3) |
C5—H5 | 0.9500 | C18—C19 | 1.391 (3) |
C6—C7 | 1.390 (4) | C19—C20 | 1.383 (3) |
C6—H6 | 0.9500 | C19—H19 | 0.9500 |
C7—C8 | 1.381 (3) | C20—C21 | 1.377 (3) |
C7—H7 | 0.9500 | C20—H20 | 0.9500 |
C8—C9 | 1.395 (3) | C21—C22 | 1.381 (3) |
C8—H8 | 0.9500 | C21—H21 | 0.9500 |
C9—C10 | 1.392 (3) | C22—C23 | 1.395 (3) |
C11—C12 | 1.468 (2) | C22—H22 | 0.9500 |
C11—H11 | 0.9500 | C23—H23 | 0.9500 |
C12—C13 | 1.3900 | ||
C9—O1—C2 | 117.18 (16) | C13—C12—C11 | 124.12 (12) |
O1—C2—C3 | 112.51 (16) | C17—C12—C11 | 115.88 (12) |
O1—C2—C18 | 108.33 (15) | C14—C13—C12 | 120.0 |
C3—C2—C18 | 114.39 (17) | C14—C13—H13 | 120.0 |
O1—C2—H2 | 107.1 | C12—C13—H13 | 120.0 |
C3—C2—H2 | 107.1 | C13—C14—C15 | 120.0 |
C18—C2—H2 | 107.1 | C13—C14—H14 | 120.0 |
C11—C3—C4 | 117.01 (19) | C15—C14—H14 | 120.0 |
C11—C3—C2 | 125.86 (19) | C14—C15—C16 | 120.0 |
C4—C3—C2 | 117.13 (17) | C14—C15—H15 | 120.0 |
O4—C4—C10 | 121.6 (2) | C16—C15—H15 | 120.0 |
O4—C4—C3 | 122.62 (19) | C17—C16—C15 | 120.0 |
C10—C4—C3 | 115.69 (18) | C17—C16—H16 | 120.0 |
C6—C5—C10 | 120.5 (2) | C15—C16—H16 | 120.0 |
C6—C5—H5 | 119.8 | C16—C17—C12 | 120.0 |
C10—C5—H5 | 119.8 | C16—C17—H17 | 120.0 |
C5—C6—C7 | 119.6 (2) | C12—C17—H17 | 120.0 |
C5—C6—H6 | 120.2 | C23—C18—C19 | 118.4 (2) |
C7—C6—H6 | 120.2 | C23—C18—C2 | 123.52 (18) |
C8—C7—C6 | 120.9 (2) | C19—C18—C2 | 118.04 (19) |
C8—C7—H7 | 119.6 | C20—C19—C18 | 120.9 (2) |
C6—C7—H7 | 119.6 | C20—C19—H19 | 119.5 |
C7—C8—C9 | 119.6 (2) | C18—C19—H19 | 119.5 |
C7—C8—H8 | 120.2 | C21—C20—C19 | 120.3 (2) |
C9—C8—H8 | 120.2 | C21—C20—H20 | 119.8 |
O1—C9—C10 | 122.82 (18) | C19—C20—H20 | 119.8 |
O1—C9—C8 | 116.91 (19) | C20—C21—C22 | 119.3 (2) |
C10—C9—C8 | 120.2 (2) | C20—C21—H21 | 120.3 |
C9—C10—C5 | 119.17 (19) | C22—C21—H21 | 120.3 |
C9—C10—C4 | 120.21 (19) | C21—C22—C23 | 120.2 (2) |
C5—C10—C4 | 120.3 (2) | C21—C22—H22 | 119.9 |
C3—C11—C12 | 131.7 (2) | C23—C22—H22 | 119.9 |
C3—C11—H11 | 114.2 | C18—C23—C22 | 120.8 (2) |
C12—C11—H11 | 114.2 | C18—C23—H23 | 119.6 |
C13—C12—C17 | 120.0 | C22—C23—H23 | 119.6 |
C9—O1—C2—C3 | −42.9 (2) | C3—C4—C10—C5 | 177.17 (19) |
C9—O1—C2—C18 | 84.6 (2) | C4—C3—C11—C12 | −179.93 (19) |
O1—C2—C3—C11 | −141.2 (2) | C2—C3—C11—C12 | 0.0 (4) |
C18—C2—C3—C11 | 94.6 (2) | C3—C11—C12—C13 | −26.0 (3) |
O1—C2—C3—C4 | 38.7 (2) | C3—C11—C12—C17 | 153.9 (2) |
C18—C2—C3—C4 | −85.5 (2) | C17—C12—C13—C14 | 0.0 |
C11—C3—C4—O4 | −10.5 (3) | C11—C12—C13—C14 | 179.93 (16) |
C2—C3—C4—O4 | 169.6 (2) | C12—C13—C14—C15 | 0.0 |
C11—C3—C4—C10 | 166.58 (19) | C13—C14—C15—C16 | 0.0 |
C2—C3—C4—C10 | −13.4 (3) | C14—C15—C16—C17 | 0.0 |
C10—C5—C6—C7 | −1.7 (4) | C15—C16—C17—C12 | 0.0 |
C5—C6—C7—C8 | 2.4 (4) | C13—C12—C17—C16 | 0.0 |
C6—C7—C8—C9 | −0.3 (3) | C11—C12—C17—C16 | −179.93 (15) |
C2—O1—C9—C10 | 21.3 (3) | O1—C2—C18—C23 | −123.2 (2) |
C2—O1—C9—C8 | −162.10 (17) | C3—C2—C18—C23 | 3.2 (3) |
C7—C8—C9—O1 | −179.08 (19) | O1—C2—C18—C19 | 57.6 (2) |
C7—C8—C9—C10 | −2.4 (3) | C3—C2—C18—C19 | −176.08 (17) |
O1—C9—C10—C5 | 179.55 (18) | C23—C18—C19—C20 | 1.1 (3) |
C8—C9—C10—C5 | 3.1 (3) | C2—C18—C19—C20 | −179.64 (17) |
O1—C9—C10—C4 | 6.5 (3) | C18—C19—C20—C21 | −0.5 (3) |
C8—C9—C10—C4 | −170.01 (19) | C19—C20—C21—C22 | −0.4 (3) |
C6—C5—C10—C9 | −1.0 (3) | C20—C21—C22—C23 | 0.7 (3) |
C6—C5—C10—C4 | 172.0 (2) | C19—C18—C23—C22 | −0.7 (3) |
O4—C4—C10—C9 | 167.2 (2) | C2—C18—C23—C22 | −180.0 (2) |
C3—C4—C10—C9 | −9.8 (3) | C21—C22—C23—C18 | −0.2 (4) |
O4—C4—C10—C5 | −5.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O4i | 0.95 | 2.47 | 3.353 (3) | 154 |
C17—H17···O4i | 0.95 | 2.64 | 3.353 (2) | 132 |
C21—H21···O4ii | 0.95 | 2.68 | 3.267 (3) | 120 |
Symmetry codes: (i) −x, y, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2. |
C23H18O2 | F(000) = 688 |
Mr = 326.37 | Dx = 1.263 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.6799 (5) Å | Cell parameters from 4576 reflections |
b = 7.9102 (2) Å | θ = 3.2–35.6° |
c = 13.1511 (3) Å | µ = 0.08 mm−1 |
β = 98.558 (3)° | T = 100 K |
V = 1715.85 (8) Å3 | Needle, colorless |
Z = 4 | 0.28 × 0.1 × 0.1 mm |
Rigaku OD SuperNova Dual source diffractometer with an Atlas detector | 3550 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source | 2927 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.031 |
Detector resolution: 10.4498 pixels mm-1 | θmax = 26.5°, θmin = 3.1° |
ω scans | h = −20→20 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −9→9 |
Tmin = 0.833, Tmax = 1.000 | l = −11→16 |
13962 measured reflections |
Refinement on F2 | Primary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.0551P)2 + 0.3869P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3550 reflections | Δρmax = 0.19 e Å−3 |
227 parameters | Δρmin = −0.23 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 | ||
O1 | 0.13016 (5) | 0.69823 (11) | 0.61728 (6) | 0.0197 (2) | |
O4 | 0.24076 (6) | 0.72695 (14) | 0.91481 (7) | 0.0330 (3) | |
C2 | 0.21464 (7) | 0.64404 (15) | 0.63602 (9) | 0.0167 (2) | |
H2 | 0.2425 | 0.6974 | 0.5818 | 0.020* | |
C3 | 0.25695 (7) | 0.70595 (14) | 0.73857 (9) | 0.0169 (2) | |
C4 | 0.20880 (8) | 0.70299 (15) | 0.82561 (9) | 0.0199 (3) | |
C5 | 0.07131 (8) | 0.65060 (17) | 0.87504 (10) | 0.0249 (3) | |
H5 | 0.0945 | 0.6518 | 0.9455 | 0.030* | |
C6 | −0.01103 (8) | 0.62868 (19) | 0.84830 (11) | 0.0304 (3) | |
H6 | −0.0445 | 0.6141 | 0.9001 | 0.036* | |
C7 | −0.04520 (8) | 0.6279 (2) | 0.74468 (11) | 0.0325 (3) | |
H7 | −0.1021 | 0.6131 | 0.7265 | 0.039* | |
C8 | 0.00253 (8) | 0.64841 (18) | 0.66811 (10) | 0.0273 (3) | |
H8 | −0.0212 | 0.6477 | 0.5978 | 0.033* | |
C9 | 0.08575 (8) | 0.67000 (15) | 0.69525 (9) | 0.0195 (3) | |
C10 | 0.12126 (7) | 0.67117 (15) | 0.79869 (9) | 0.0196 (3) | |
C11 | 0.33397 (7) | 0.76156 (15) | 0.75777 (9) | 0.0185 (3) | |
H11 | 0.3504 | 0.7991 | 0.8263 | 0.022* | |
C12 | 0.39695 (7) | 0.77435 (15) | 0.69160 (9) | 0.0192 (3) | |
C13 | 0.39774 (7) | 0.68092 (16) | 0.60070 (9) | 0.0210 (3) | |
H13 | 0.3545 | 0.6054 | 0.5780 | 0.025* | |
C14 | 0.46100 (8) | 0.69780 (17) | 0.54379 (9) | 0.0225 (3) | |
H14 | 0.4597 | 0.6347 | 0.4821 | 0.027* | |
C15 | 0.52641 (8) | 0.80485 (17) | 0.57477 (10) | 0.0254 (3) | |
C16 | 0.52603 (8) | 0.89659 (18) | 0.66538 (11) | 0.0295 (3) | |
H16 | 0.5699 | 0.9705 | 0.6884 | 0.035* | |
C17 | 0.46310 (8) | 0.88198 (17) | 0.72228 (10) | 0.0253 (3) | |
H17 | 0.4646 | 0.9462 | 0.7836 | 0.030* | |
C18 | 0.59644 (9) | 0.8178 (2) | 0.51466 (12) | 0.0346 (3) | |
H18A | 0.6390 | 0.7379 | 0.5426 | 0.052* | |
H18B | 0.6182 | 0.9331 | 0.5200 | 0.052* | |
H18C | 0.5776 | 0.7908 | 0.4423 | 0.052* | |
C21 | 0.21801 (7) | 0.45373 (15) | 0.62104 (9) | 0.0177 (3) | |
C22 | 0.18813 (7) | 0.38872 (16) | 0.52380 (9) | 0.0220 (3) | |
H22 | 0.1658 | 0.4631 | 0.4702 | 0.026* | |
C23 | 0.19088 (8) | 0.21637 (17) | 0.50521 (10) | 0.0267 (3) | |
H23 | 0.1705 | 0.1731 | 0.4390 | 0.032* | |
C24 | 0.22339 (8) | 0.10705 (17) | 0.58321 (11) | 0.0284 (3) | |
H24 | 0.2254 | −0.0109 | 0.5704 | 0.034* | |
C25 | 0.25287 (8) | 0.17031 (17) | 0.67978 (11) | 0.0285 (3) | |
H25 | 0.2749 | 0.0955 | 0.7332 | 0.034* | |
C26 | 0.25024 (8) | 0.34321 (16) | 0.69859 (10) | 0.0227 (3) | |
H26 | 0.2706 | 0.3860 | 0.7649 | 0.027* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0176 (4) | 0.0237 (5) | 0.0177 (4) | 0.0045 (3) | 0.0022 (3) | 0.0018 (3) |
O4 | 0.0259 (5) | 0.0560 (7) | 0.0170 (4) | −0.0066 (5) | 0.0030 (4) | −0.0072 (4) |
C2 | 0.0152 (6) | 0.0182 (6) | 0.0167 (5) | 0.0011 (4) | 0.0023 (4) | 0.0012 (4) |
C3 | 0.0197 (6) | 0.0134 (6) | 0.0174 (6) | 0.0020 (4) | 0.0022 (5) | 0.0006 (4) |
C4 | 0.0219 (6) | 0.0207 (6) | 0.0173 (6) | 0.0009 (5) | 0.0029 (5) | −0.0007 (5) |
C5 | 0.0258 (7) | 0.0278 (7) | 0.0219 (6) | 0.0013 (5) | 0.0062 (5) | −0.0014 (5) |
C6 | 0.0251 (7) | 0.0378 (8) | 0.0308 (7) | −0.0009 (6) | 0.0126 (6) | −0.0028 (6) |
C7 | 0.0180 (7) | 0.0430 (9) | 0.0371 (8) | 0.0000 (6) | 0.0055 (6) | −0.0056 (6) |
C8 | 0.0211 (7) | 0.0343 (8) | 0.0254 (6) | 0.0034 (6) | 0.0004 (5) | −0.0019 (6) |
C9 | 0.0202 (6) | 0.0177 (6) | 0.0211 (6) | 0.0029 (5) | 0.0047 (5) | −0.0003 (5) |
C10 | 0.0207 (6) | 0.0180 (6) | 0.0203 (6) | 0.0016 (5) | 0.0039 (5) | −0.0017 (5) |
C11 | 0.0220 (6) | 0.0168 (6) | 0.0162 (5) | 0.0010 (5) | 0.0011 (5) | −0.0011 (4) |
C12 | 0.0174 (6) | 0.0197 (6) | 0.0199 (6) | 0.0023 (5) | 0.0011 (5) | 0.0018 (5) |
C13 | 0.0184 (6) | 0.0213 (6) | 0.0224 (6) | 0.0005 (5) | 0.0004 (5) | −0.0010 (5) |
C14 | 0.0214 (6) | 0.0264 (7) | 0.0194 (6) | 0.0046 (5) | 0.0015 (5) | −0.0006 (5) |
C15 | 0.0210 (6) | 0.0269 (7) | 0.0291 (7) | 0.0024 (5) | 0.0062 (5) | 0.0031 (5) |
C16 | 0.0214 (7) | 0.0298 (7) | 0.0376 (8) | −0.0074 (5) | 0.0051 (6) | −0.0058 (6) |
C17 | 0.0235 (7) | 0.0270 (7) | 0.0251 (6) | −0.0031 (5) | 0.0024 (5) | −0.0068 (5) |
C18 | 0.0244 (7) | 0.0407 (9) | 0.0413 (8) | −0.0007 (6) | 0.0132 (6) | 0.0009 (7) |
C21 | 0.0146 (6) | 0.0182 (6) | 0.0212 (6) | −0.0013 (4) | 0.0055 (5) | −0.0009 (5) |
C22 | 0.0201 (6) | 0.0230 (7) | 0.0229 (6) | −0.0012 (5) | 0.0030 (5) | −0.0015 (5) |
C23 | 0.0233 (7) | 0.0261 (7) | 0.0320 (7) | −0.0058 (5) | 0.0080 (5) | −0.0094 (5) |
C24 | 0.0249 (7) | 0.0166 (6) | 0.0459 (8) | −0.0014 (5) | 0.0132 (6) | −0.0038 (6) |
C25 | 0.0272 (7) | 0.0211 (7) | 0.0376 (8) | 0.0036 (5) | 0.0066 (6) | 0.0062 (6) |
C26 | 0.0222 (6) | 0.0215 (6) | 0.0243 (6) | 0.0012 (5) | 0.0038 (5) | 0.0020 (5) |
O1—C9 | 1.3696 (14) | C13—C14 | 1.3879 (17) |
O1—C2 | 1.4582 (14) | C13—H13 | 0.9500 |
O4—C4 | 1.2288 (15) | C14—C15 | 1.3933 (19) |
C2—C3 | 1.5078 (16) | C14—H14 | 0.9500 |
C2—C21 | 1.5204 (16) | C15—C16 | 1.3960 (19) |
C2—H2 | 1.0000 | C15—C18 | 1.5082 (18) |
C3—C11 | 1.3458 (17) | C16—C17 | 1.3817 (19) |
C3—C4 | 1.4932 (16) | C16—H16 | 0.9500 |
C4—C10 | 1.4720 (17) | C17—H17 | 0.9500 |
C5—C6 | 1.3770 (19) | C18—H18A | 0.9800 |
C5—C10 | 1.4064 (17) | C18—H18B | 0.9800 |
C5—H5 | 0.9500 | C18—H18C | 0.9800 |
C6—C7 | 1.397 (2) | C21—C26 | 1.3893 (17) |
C6—H6 | 0.9500 | C21—C22 | 1.3995 (17) |
C7—C8 | 1.3830 (19) | C22—C23 | 1.3870 (18) |
C7—H7 | 0.9500 | C22—H22 | 0.9500 |
C8—C9 | 1.3915 (18) | C23—C24 | 1.389 (2) |
C8—H8 | 0.9500 | C23—H23 | 0.9500 |
C9—C10 | 1.4006 (17) | C24—C25 | 1.385 (2) |
C11—C12 | 1.4637 (17) | C24—H24 | 0.9500 |
C11—H11 | 0.9500 | C25—C26 | 1.3917 (19) |
C12—C17 | 1.4046 (17) | C25—H25 | 0.9500 |
C12—C13 | 1.4072 (17) | C26—H26 | 0.9500 |
C9—O1—C2 | 116.24 (9) | C14—C13—H13 | 119.6 |
O1—C2—C3 | 111.57 (9) | C12—C13—H13 | 119.6 |
O1—C2—C21 | 108.82 (9) | C13—C14—C15 | 121.73 (12) |
C3—C2—C21 | 114.59 (10) | C13—C14—H14 | 119.1 |
O1—C2—H2 | 107.2 | C15—C14—H14 | 119.1 |
C3—C2—H2 | 107.2 | C14—C15—C16 | 117.56 (12) |
C21—C2—H2 | 107.2 | C14—C15—C18 | 121.46 (12) |
C11—C3—C4 | 117.95 (10) | C16—C15—C18 | 120.96 (13) |
C11—C3—C2 | 125.50 (11) | C17—C16—C15 | 121.27 (12) |
C4—C3—C2 | 116.55 (10) | C17—C16—H16 | 119.4 |
O4—C4—C10 | 122.00 (11) | C15—C16—H16 | 119.4 |
O4—C4—C3 | 121.53 (11) | C16—C17—C12 | 121.52 (12) |
C10—C4—C3 | 116.47 (10) | C16—C17—H17 | 119.2 |
C6—C5—C10 | 120.44 (12) | C12—C17—H17 | 119.2 |
C6—C5—H5 | 119.8 | C15—C18—H18A | 109.5 |
C10—C5—H5 | 119.8 | C15—C18—H18B | 109.5 |
C5—C6—C7 | 119.76 (12) | H18A—C18—H18B | 109.5 |
C5—C6—H6 | 120.1 | C15—C18—H18C | 109.5 |
C7—C6—H6 | 120.1 | H18A—C18—H18C | 109.5 |
C8—C7—C6 | 120.96 (13) | H18B—C18—H18C | 109.5 |
C8—C7—H7 | 119.5 | C26—C21—C22 | 119.07 (12) |
C6—C7—H7 | 119.5 | C26—C21—C2 | 123.07 (11) |
C7—C8—C9 | 119.21 (12) | C22—C21—C2 | 117.85 (11) |
C7—C8—H8 | 120.4 | C23—C22—C21 | 120.37 (12) |
C9—C8—H8 | 120.4 | C23—C22—H22 | 119.8 |
O1—C9—C8 | 117.26 (11) | C21—C22—H22 | 119.8 |
O1—C9—C10 | 121.89 (11) | C22—C23—C24 | 120.09 (12) |
C8—C9—C10 | 120.77 (11) | C22—C23—H23 | 120.0 |
C9—C10—C5 | 118.87 (12) | C24—C23—H23 | 120.0 |
C9—C10—C4 | 119.72 (11) | C25—C24—C23 | 119.90 (12) |
C5—C10—C4 | 121.33 (11) | C25—C24—H24 | 120.0 |
C3—C11—C12 | 131.34 (11) | C23—C24—H24 | 120.0 |
C3—C11—H11 | 114.3 | C24—C25—C26 | 120.11 (13) |
C12—C11—H11 | 114.3 | C24—C25—H25 | 119.9 |
C17—C12—C13 | 117.13 (11) | C26—C25—H25 | 119.9 |
C17—C12—C11 | 118.27 (11) | C21—C26—C25 | 120.45 (12) |
C13—C12—C11 | 124.55 (11) | C21—C26—H26 | 119.8 |
C14—C13—C12 | 120.78 (12) | C25—C26—H26 | 119.8 |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O4i | 1.00 | 2.27 | 3.1737 (14) | 149 |
C5—H5···O1ii | 0.95 | 2.54 | 3.4076 (15) | 152 |
C24—H24···O4iii | 0.95 | 2.71 | 3.4871 (17) | 140 |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+3/2, z+1/2; (iii) x, −y+1/2, z−1/2. |
C23H18O2 | Z = 2 |
Mr = 326.37 | F(000) = 344 |
Triclinic, P1 | Dx = 1.275 Mg m−3 |
a = 8.9094 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.6578 (3) Å | Cell parameters from 3948 reflections |
c = 10.9044 (4) Å | θ = 3.5–36.1° |
α = 104.378 (3)° | µ = 0.08 mm−1 |
β = 109.425 (3)° | T = 100 K |
γ = 91.902 (3)° | Needle, colorless |
V = 850.24 (5) Å3 | 0.28 × 0.1 × 0.08 mm |
Rigaku OD SuperNova Dual source diffractometer with an Atlas detector | 3509 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source | 2999 reflections with I > 2σ(I) |
Detector resolution: 10.4498 pixels mm-1 | Rint = 0.021 |
ω scans | θmax = 26.5°, θmin = 3.1° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −11→11 |
Tmin = 0.736, Tmax = 1.000 | k = −12→12 |
7284 measured reflections | l = −13→10 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.098 | w = 1/[σ2(Fo2) + (0.0439P)2 + 0.2079P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3509 reflections | Δρmax = 0.24 e Å−3 |
227 parameters | Δρmin = −0.21 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 | ||
O1 | 0.57118 (10) | 0.44640 (9) | 0.37188 (8) | 0.0200 (2) | |
O4 | 0.38766 (10) | 0.03505 (9) | 0.32719 (8) | 0.0229 (2) | |
C21 | 0.66313 (13) | 0.29543 (13) | 0.20350 (11) | 0.0170 (2) | |
C12 | 0.89045 (14) | 0.16807 (12) | 0.54388 (12) | 0.0192 (3) | |
C2 | 0.66990 (14) | 0.33222 (12) | 0.35024 (11) | 0.0172 (2) | |
H2 | 0.7834 | 0.3701 | 0.4101 | 0.021* | |
C3 | 0.61964 (14) | 0.20436 (12) | 0.39022 (11) | 0.0176 (2) | |
C11 | 0.71562 (14) | 0.13781 (13) | 0.47467 (11) | 0.0188 (3) | |
H11 | 0.6638 | 0.0611 | 0.4920 | 0.023* | |
C9 | 0.40917 (14) | 0.40489 (13) | 0.31451 (11) | 0.0188 (3) | |
C4 | 0.44417 (14) | 0.15501 (13) | 0.33244 (11) | 0.0179 (2) | |
C26 | 0.66779 (14) | 0.15547 (13) | 0.13257 (12) | 0.0204 (3) | |
H26 | 0.6718 | 0.0796 | 0.1744 | 0.024* | |
C10 | 0.34138 (14) | 0.26263 (13) | 0.28726 (11) | 0.0188 (3) | |
C13 | 0.99590 (15) | 0.20421 (13) | 0.48267 (12) | 0.0221 (3) | |
H13 | 0.9549 | 0.2119 | 0.3926 | 0.026* | |
C17 | 0.95460 (15) | 0.15826 (13) | 0.67717 (12) | 0.0203 (3) | |
H17 | 0.8844 | 0.1306 | 0.7185 | 0.024* | |
C16 | 1.11883 (15) | 0.18806 (13) | 0.75045 (12) | 0.0215 (3) | |
C5 | 0.17385 (15) | 0.22886 (14) | 0.22882 (12) | 0.0228 (3) | |
H5 | 0.1266 | 0.1325 | 0.2086 | 0.027* | |
C22 | 0.65751 (14) | 0.40519 (13) | 0.14018 (12) | 0.0208 (3) | |
H22 | 0.6544 | 0.5013 | 0.1876 | 0.025* | |
C25 | 0.66659 (15) | 0.12572 (14) | 0.00015 (12) | 0.0230 (3) | |
H25 | 0.6695 | 0.0297 | −0.0476 | 0.028* | |
C24 | 0.66114 (14) | 0.23528 (14) | −0.06185 (12) | 0.0221 (3) | |
H24 | 0.6607 | 0.2149 | −0.1518 | 0.027* | |
C14 | 1.16003 (15) | 0.22879 (14) | 0.55301 (13) | 0.0249 (3) | |
H14 | 1.2311 | 0.2514 | 0.5103 | 0.030* | |
C15 | 1.22082 (15) | 0.22054 (13) | 0.68555 (12) | 0.0234 (3) | |
H15 | 1.3335 | 0.2373 | 0.7327 | 0.028* | |
C23 | 0.65634 (15) | 0.37523 (14) | 0.00852 (12) | 0.0232 (3) | |
H23 | 0.6522 | 0.4508 | −0.0336 | 0.028* | |
C8 | 0.31165 (16) | 0.51168 (14) | 0.28802 (12) | 0.0243 (3) | |
H8 | 0.3579 | 0.6084 | 0.3085 | 0.029* | |
C6 | 0.07720 (15) | 0.33358 (16) | 0.20038 (13) | 0.0274 (3) | |
H6 | −0.0359 | 0.3095 | 0.1599 | 0.033* | |
C7 | 0.14682 (16) | 0.47552 (15) | 0.23157 (13) | 0.0279 (3) | |
H7 | 0.0801 | 0.5482 | 0.2138 | 0.033* | |
C18 | 1.18325 (16) | 0.18957 (15) | 0.89766 (12) | 0.0283 (3) | |
H18A | 1.1300 | 0.1062 | 0.9099 | 0.042* | |
H18B | 1.1624 | 0.2785 | 0.9527 | 0.042* | |
H18C | 1.2991 | 0.1850 | 0.9259 | 0.042* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0226 (4) | 0.0158 (4) | 0.0191 (4) | 0.0016 (3) | 0.0072 (3) | 0.0009 (3) |
O4 | 0.0240 (4) | 0.0210 (5) | 0.0226 (4) | −0.0023 (3) | 0.0066 (4) | 0.0069 (4) |
C21 | 0.0138 (5) | 0.0185 (6) | 0.0176 (5) | 0.0001 (4) | 0.0045 (4) | 0.0046 (5) |
C12 | 0.0228 (6) | 0.0134 (6) | 0.0191 (6) | 0.0031 (4) | 0.0056 (5) | 0.0028 (4) |
C2 | 0.0176 (5) | 0.0157 (6) | 0.0168 (5) | 0.0013 (4) | 0.0051 (4) | 0.0031 (4) |
C3 | 0.0212 (6) | 0.0166 (6) | 0.0141 (5) | 0.0012 (4) | 0.0071 (4) | 0.0014 (4) |
C11 | 0.0230 (6) | 0.0162 (6) | 0.0167 (5) | 0.0001 (5) | 0.0083 (5) | 0.0022 (4) |
C9 | 0.0222 (6) | 0.0217 (6) | 0.0121 (5) | 0.0032 (5) | 0.0072 (4) | 0.0025 (5) |
C4 | 0.0225 (6) | 0.0191 (6) | 0.0123 (5) | 0.0004 (5) | 0.0078 (4) | 0.0027 (4) |
C26 | 0.0240 (6) | 0.0176 (6) | 0.0191 (6) | 0.0009 (5) | 0.0068 (5) | 0.0056 (5) |
C10 | 0.0214 (6) | 0.0221 (6) | 0.0138 (5) | 0.0032 (5) | 0.0079 (4) | 0.0043 (5) |
C13 | 0.0244 (6) | 0.0227 (7) | 0.0180 (6) | 0.0027 (5) | 0.0068 (5) | 0.0048 (5) |
C17 | 0.0252 (6) | 0.0155 (6) | 0.0211 (6) | 0.0038 (5) | 0.0088 (5) | 0.0055 (5) |
C16 | 0.0286 (7) | 0.0141 (6) | 0.0181 (6) | 0.0043 (5) | 0.0050 (5) | 0.0026 (5) |
C5 | 0.0224 (6) | 0.0290 (7) | 0.0182 (6) | 0.0013 (5) | 0.0086 (5) | 0.0067 (5) |
C22 | 0.0219 (6) | 0.0169 (6) | 0.0245 (6) | 0.0032 (5) | 0.0091 (5) | 0.0057 (5) |
C25 | 0.0268 (6) | 0.0195 (6) | 0.0200 (6) | 0.0015 (5) | 0.0076 (5) | 0.0019 (5) |
C24 | 0.0212 (6) | 0.0289 (7) | 0.0167 (5) | 0.0035 (5) | 0.0062 (5) | 0.0075 (5) |
C14 | 0.0251 (6) | 0.0256 (7) | 0.0241 (6) | 0.0016 (5) | 0.0105 (5) | 0.0044 (5) |
C15 | 0.0204 (6) | 0.0200 (6) | 0.0242 (6) | 0.0017 (5) | 0.0037 (5) | 0.0019 (5) |
C23 | 0.0243 (6) | 0.0247 (7) | 0.0250 (6) | 0.0052 (5) | 0.0099 (5) | 0.0127 (5) |
C8 | 0.0328 (7) | 0.0217 (7) | 0.0194 (6) | 0.0075 (5) | 0.0111 (5) | 0.0043 (5) |
C6 | 0.0206 (6) | 0.0400 (8) | 0.0231 (6) | 0.0072 (5) | 0.0085 (5) | 0.0098 (6) |
C7 | 0.0301 (7) | 0.0331 (8) | 0.0238 (6) | 0.0156 (6) | 0.0115 (5) | 0.0096 (6) |
C18 | 0.0315 (7) | 0.0295 (7) | 0.0205 (6) | 0.0051 (5) | 0.0045 (5) | 0.0073 (5) |
O1—C9 | 1.3682 (14) | C17—H17 | 0.9500 |
O1—C2 | 1.4555 (14) | C16—C15 | 1.3942 (18) |
O4—C4 | 1.2281 (14) | C16—C18 | 1.5105 (16) |
C21—C26 | 1.3903 (17) | C5—C6 | 1.3771 (19) |
C21—C22 | 1.3953 (17) | C5—H5 | 0.9500 |
C21—C2 | 1.5305 (15) | C22—C23 | 1.3887 (17) |
C12—C13 | 1.4004 (17) | C22—H22 | 0.9500 |
C12—C17 | 1.4027 (16) | C25—C24 | 1.3841 (18) |
C12—C11 | 1.4695 (16) | C25—H25 | 0.9500 |
C2—C3 | 1.5086 (16) | C24—C23 | 1.3885 (18) |
C2—H2 | 1.0000 | C24—H24 | 0.9500 |
C3—C11 | 1.3413 (17) | C14—C15 | 1.3885 (18) |
C3—C4 | 1.4881 (15) | C14—H14 | 0.9500 |
C11—H11 | 0.9500 | C15—H15 | 0.9500 |
C9—C8 | 1.3938 (17) | C23—H23 | 0.9500 |
C9—C10 | 1.4012 (17) | C8—C7 | 1.3839 (18) |
C4—C10 | 1.4762 (17) | C8—H8 | 0.9500 |
C26—C25 | 1.3969 (16) | C6—C7 | 1.397 (2) |
C26—H26 | 0.9500 | C6—H6 | 0.9500 |
C10—C5 | 1.4043 (16) | C7—H7 | 0.9500 |
C13—C14 | 1.3868 (17) | C18—H18A | 0.9800 |
C13—H13 | 0.9500 | C18—H18B | 0.9800 |
C17—C16 | 1.3937 (17) | C18—H18C | 0.9800 |
C9—O1—C2 | 115.14 (9) | C17—C16—C18 | 120.52 (11) |
C26—C21—C22 | 118.86 (11) | C15—C16—C18 | 121.13 (11) |
C26—C21—C2 | 121.58 (10) | C6—C5—C10 | 120.87 (12) |
C22—C21—C2 | 119.53 (11) | C6—C5—H5 | 119.6 |
C13—C12—C17 | 118.55 (11) | C10—C5—H5 | 119.6 |
C13—C12—C11 | 123.22 (10) | C23—C22—C21 | 120.62 (12) |
C17—C12—C11 | 118.22 (11) | C23—C22—H22 | 119.7 |
O1—C2—C3 | 110.50 (9) | C21—C22—H22 | 119.7 |
O1—C2—C21 | 109.10 (9) | C24—C25—C26 | 120.39 (12) |
C3—C2—C21 | 113.52 (9) | C24—C25—H25 | 119.8 |
O1—C2—H2 | 107.8 | C26—C25—H25 | 119.8 |
C3—C2—H2 | 107.8 | C25—C24—C23 | 119.46 (11) |
C21—C2—H2 | 107.8 | C25—C24—H24 | 120.3 |
C11—C3—C4 | 118.88 (10) | C23—C24—H24 | 120.3 |
C11—C3—C2 | 126.48 (11) | C13—C14—C15 | 120.26 (12) |
C4—C3—C2 | 114.58 (10) | C13—C14—H14 | 119.9 |
C3—C11—C12 | 128.46 (11) | C15—C14—H14 | 119.9 |
C3—C11—H11 | 115.8 | C14—C15—C16 | 120.92 (11) |
C12—C11—H11 | 115.8 | C14—C15—H15 | 119.5 |
O1—C9—C8 | 117.18 (11) | C16—C15—H15 | 119.5 |
O1—C9—C10 | 122.27 (11) | C24—C23—C22 | 120.31 (11) |
C8—C9—C10 | 120.51 (11) | C24—C23—H23 | 119.8 |
O4—C4—C10 | 121.96 (11) | C22—C23—H23 | 119.8 |
O4—C4—C3 | 122.58 (11) | C7—C8—C9 | 119.42 (12) |
C10—C4—C3 | 115.40 (10) | C7—C8—H8 | 120.3 |
C21—C26—C25 | 120.37 (11) | C9—C8—H8 | 120.3 |
C21—C26—H26 | 119.8 | C5—C6—C7 | 119.48 (12) |
C25—C26—H26 | 119.8 | C5—C6—H6 | 120.3 |
C9—C10—C5 | 118.78 (11) | C7—C6—H6 | 120.3 |
C9—C10—C4 | 119.87 (11) | C8—C7—C6 | 120.90 (12) |
C5—C10—C4 | 121.05 (11) | C8—C7—H7 | 119.5 |
C14—C13—C12 | 120.24 (11) | C6—C7—H7 | 119.5 |
C14—C13—H13 | 119.9 | C16—C18—H18A | 109.5 |
C12—C13—H13 | 119.9 | C16—C18—H18B | 109.5 |
C16—C17—C12 | 121.63 (11) | H18A—C18—H18B | 109.5 |
C16—C17—H17 | 119.2 | C16—C18—H18C | 109.5 |
C12—C17—H17 | 119.2 | H18A—C18—H18C | 109.5 |
C17—C16—C15 | 118.32 (11) | H18B—C18—H18C | 109.5 |
C9—O1—C2—C3 | −51.97 (12) | C3—C4—C10—C9 | −7.36 (15) |
C9—O1—C2—C21 | 73.51 (11) | O4—C4—C10—C5 | −3.72 (17) |
C26—C21—C2—O1 | −145.49 (10) | C3—C4—C10—C5 | 178.94 (10) |
C22—C21—C2—O1 | 36.67 (14) | C17—C12—C13—C14 | 0.34 (18) |
C26—C21—C2—C3 | −21.79 (15) | C11—C12—C13—C14 | −178.77 (12) |
C22—C21—C2—C3 | 160.38 (10) | C13—C12—C17—C16 | 2.12 (18) |
O1—C2—C3—C11 | −127.71 (12) | C11—C12—C17—C16 | −178.73 (11) |
C21—C2—C3—C11 | 109.35 (13) | C12—C17—C16—C15 | −3.55 (18) |
O1—C2—C3—C4 | 49.49 (12) | C12—C17—C16—C18 | 174.54 (12) |
C21—C2—C3—C4 | −73.45 (13) | C9—C10—C5—C6 | −0.92 (17) |
C4—C3—C11—C12 | −179.62 (11) | C4—C10—C5—C6 | 172.84 (11) |
C2—C3—C11—C12 | −2.5 (2) | C26—C21—C22—C23 | 0.09 (17) |
C13—C12—C11—C3 | −39.46 (19) | C2—C21—C22—C23 | 177.99 (11) |
C17—C12—C11—C3 | 141.43 (13) | C21—C26—C25—C24 | 0.16 (18) |
C2—O1—C9—C8 | −157.01 (10) | C26—C25—C24—C23 | −0.21 (18) |
C2—O1—C9—C10 | 25.25 (14) | C12—C13—C14—C15 | −1.3 (2) |
C11—C3—C4—O4 | −20.52 (17) | C13—C14—C15—C16 | −0.2 (2) |
C2—C3—C4—O4 | 162.05 (11) | C17—C16—C15—C14 | 2.57 (19) |
C11—C3—C4—C10 | 156.80 (11) | C18—C16—C15—C14 | −175.51 (12) |
C2—C3—C4—C10 | −20.63 (14) | C25—C24—C23—C22 | 0.20 (18) |
C22—C21—C26—C25 | −0.10 (17) | C21—C22—C23—C24 | −0.15 (18) |
C2—C21—C26—C25 | −177.95 (11) | O1—C9—C8—C7 | −179.21 (10) |
O1—C9—C10—C5 | 179.68 (10) | C10—C9—C8—C7 | −1.43 (17) |
C8—C9—C10—C5 | 2.01 (17) | C10—C5—C6—C7 | −0.74 (18) |
O1—C9—C10—C4 | 5.84 (16) | C9—C8—C7—C6 | −0.26 (18) |
C8—C9—C10—C4 | −171.83 (10) | C5—C6—C7—C8 | 1.35 (19) |
O4—C4—C10—C9 | 169.98 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O4i | 0.95 | 2.54 | 3.3635 (14) | 145 |
C17—H17···O4i | 0.95 | 2.69 | 3.5025 (15) | 144 |
C24—H24···O4ii | 0.95 | 2.60 | 3.2731 (15) | 128 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y, −z. |
C23H18O3 | F(000) = 2160 |
Mr = 342.37 | Dx = 1.306 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 23.4111 (3) Å | Cell parameters from 7810 reflections |
b = 8.0027 (1) Å | θ = 2.6–74.1° |
c = 28.1094 (5) Å | µ = 0.69 mm−1 |
β = 97.156 (1)° | T = 100 K |
V = 5225.33 (13) Å3 | Needle, colorless |
Z = 12 | 0.28 × 0.1 × 0.08 mm |
Rigaku OD SuperNova Dual source diffractometer with an Atlas detector | 7742 reflections with I > 2σ(I) |
ω scans | Rint = 0.022 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | θmax = 67.5°, θmin = 2.3° |
Tmin = 0.997, Tmax = 1.000 | h = −26→28 |
15971 measured reflections | k = −9→7 |
9323 independent reflections | l = −33→30 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0515P)2 + 0.9818P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
9323 reflections | Δρmax = 0.20 e Å−3 |
706 parameters | Δρmin = −0.21 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 | ||
O1 | 0.10459 (3) | 0.83638 (11) | 0.53474 (3) | 0.01769 (18) | |
O4 | 0.26145 (4) | 0.77397 (13) | 0.48650 (3) | 0.0270 (2) | |
O3 | 0.31526 (4) | 0.78657 (13) | 0.78489 (3) | 0.0293 (2) | |
C5 | 0.16094 (5) | 0.81050 (15) | 0.46836 (4) | 0.0195 (3) | |
C4 | 0.21516 (5) | 0.80412 (15) | 0.50102 (4) | 0.0190 (3) | |
C6 | 0.16063 (6) | 0.79075 (18) | 0.41871 (5) | 0.0248 (3) | |
H6 | 0.1960 | 0.7805 | 0.4057 | 0.030* | |
C3 | 0.21023 (5) | 0.83055 (14) | 0.55297 (4) | 0.0171 (2) | |
C17 | 0.25594 (5) | 0.78916 (15) | 0.58462 (5) | 0.0186 (2) | |
H17 | 0.2877 | 0.7476 | 0.5702 | 0.022* | |
C21 | 0.29676 (6) | 0.79508 (16) | 0.73726 (5) | 0.0221 (3) | |
C9 | 0.05653 (6) | 0.82182 (18) | 0.45664 (5) | 0.0253 (3) | |
H9 | 0.0210 | 0.8326 | 0.4694 | 0.030* | |
C19 | 0.23508 (5) | 0.88924 (15) | 0.66704 (4) | 0.0187 (2) | |
H19 | 0.2033 | 0.9545 | 0.6534 | 0.022* | |
C23 | 0.31335 (5) | 0.70289 (17) | 0.65885 (5) | 0.0229 (3) | |
H23 | 0.3355 | 0.6391 | 0.6393 | 0.028* | |
C18 | 0.26619 (5) | 0.79578 (15) | 0.63689 (5) | 0.0192 (3) | |
C16 | 0.10377 (5) | 1.16182 (16) | 0.58418 (5) | 0.0214 (3) | |
H16 | 0.0767 | 1.0927 | 0.5973 | 0.026* | |
C2 | 0.15441 (5) | 0.89981 (15) | 0.56591 (4) | 0.0162 (2) | |
H2 | 0.1505 | 0.8617 | 0.5992 | 0.019* | |
C14 | 0.13611 (6) | 1.43522 (16) | 0.56434 (5) | 0.0252 (3) | |
H14 | 0.1310 | 1.5530 | 0.5636 | 0.030* | |
C15 | 0.09655 (6) | 1.33437 (17) | 0.58351 (5) | 0.0251 (3) | |
H15 | 0.0646 | 1.3830 | 0.5961 | 0.030* | |
C10 | 0.10837 (5) | 0.82584 (15) | 0.48687 (4) | 0.0184 (2) | |
C11 | 0.15050 (5) | 1.08964 (15) | 0.56562 (4) | 0.0173 (2) | |
C12 | 0.19031 (5) | 1.19147 (16) | 0.54688 (4) | 0.0194 (3) | |
H12 | 0.2224 | 1.1431 | 0.5345 | 0.023* | |
C20 | 0.24966 (5) | 0.88868 (16) | 0.71658 (5) | 0.0202 (3) | |
H20 | 0.2276 | 0.9519 | 0.7363 | 0.024* | |
C13 | 0.18315 (6) | 1.36457 (17) | 0.54629 (5) | 0.0236 (3) | |
H13 | 0.2104 | 1.4341 | 0.5336 | 0.028* | |
C8 | 0.05741 (6) | 0.8019 (2) | 0.40788 (5) | 0.0317 (3) | |
H8 | 0.0222 | 0.7989 | 0.3871 | 0.038* | |
C22 | 0.32840 (6) | 0.70158 (17) | 0.70782 (5) | 0.0251 (3) | |
H22 | 0.3603 | 0.6370 | 0.7215 | 0.030* | |
C7 | 0.10937 (6) | 0.7862 (2) | 0.38870 (5) | 0.0307 (3) | |
H7 | 0.1094 | 0.7724 | 0.3551 | 0.037* | |
C211 | 0.28785 (6) | 0.8935 (2) | 0.81596 (5) | 0.0321 (3) | |
H21A | 0.2464 | 0.8712 | 0.8119 | 0.048* | |
H21B | 0.2946 | 1.0105 | 0.8080 | 0.048* | |
H21C | 0.3038 | 0.8721 | 0.8493 | 0.048* | |
O31 | 0.56062 (3) | 0.27594 (11) | 0.79683 (3) | 0.01768 (18) | |
O34 | 0.40526 (4) | 0.20680 (13) | 0.84703 (3) | 0.0264 (2) | |
C40 | 0.55790 (5) | 0.26249 (15) | 0.84483 (4) | 0.0185 (2) | |
O33 | 0.34425 (4) | 0.32326 (14) | 0.55019 (3) | 0.0311 (2) | |
C41 | 0.51536 (5) | 0.53223 (15) | 0.76805 (4) | 0.0174 (2) | |
C42 | 0.47572 (6) | 0.63647 (16) | 0.78610 (4) | 0.0209 (3) | |
H42 | 0.4431 | 0.5901 | 0.7983 | 0.025* | |
C33 | 0.45460 (5) | 0.27542 (15) | 0.78040 (4) | 0.0175 (2) | |
C46 | 0.56266 (6) | 0.60212 (17) | 0.74971 (5) | 0.0228 (3) | |
H46 | 0.5895 | 0.5315 | 0.7369 | 0.027* | |
C48 | 0.39692 (5) | 0.26975 (16) | 0.69692 (5) | 0.0194 (3) | |
C36 | 0.50724 (6) | 0.22330 (17) | 0.91374 (5) | 0.0244 (3) | |
H36 | 0.4722 | 0.2119 | 0.9272 | 0.029* | |
C47 | 0.40779 (5) | 0.24452 (15) | 0.74877 (5) | 0.0192 (3) | |
H47 | 0.3763 | 0.1982 | 0.7625 | 0.023* | |
C52 | 0.33472 (6) | 0.19928 (18) | 0.62375 (5) | 0.0274 (3) | |
H52 | 0.3035 | 0.1363 | 0.6081 | 0.033* | |
C35 | 0.50597 (5) | 0.24518 (15) | 0.86402 (5) | 0.0196 (3) | |
C43 | 0.48379 (6) | 0.80906 (17) | 0.78637 (5) | 0.0267 (3) | |
H43 | 0.4567 | 0.8801 | 0.7987 | 0.032* | |
C34 | 0.45110 (5) | 0.24053 (15) | 0.83209 (5) | 0.0191 (3) | |
C45 | 0.57070 (6) | 0.77351 (18) | 0.75011 (5) | 0.0279 (3) | |
H45 | 0.6031 | 0.8203 | 0.7377 | 0.034* | |
C37 | 0.55895 (6) | 0.2183 (2) | 0.94308 (5) | 0.0305 (3) | |
H37 | 0.5596 | 0.2035 | 0.9767 | 0.037* | |
C51 | 0.36454 (6) | 0.31041 (17) | 0.59743 (5) | 0.0223 (3) | |
C50 | 0.41129 (5) | 0.39894 (16) | 0.62069 (5) | 0.0200 (3) | |
H50 | 0.4324 | 0.4729 | 0.6031 | 0.024* | |
C44 | 0.53120 (7) | 0.87706 (17) | 0.76868 (5) | 0.0292 (3) | |
H44 | 0.5368 | 0.9947 | 0.7692 | 0.035* | |
C49 | 0.42686 (5) | 0.37853 (16) | 0.66989 (4) | 0.0195 (3) | |
H49 | 0.4586 | 0.4400 | 0.6854 | 0.023* | |
C39 | 0.61035 (6) | 0.25690 (18) | 0.87438 (5) | 0.0252 (3) | |
H39 | 0.6456 | 0.2681 | 0.8611 | 0.030* | |
C32 | 0.51044 (5) | 0.34316 (15) | 0.76700 (4) | 0.0166 (2) | |
H32 | 0.5133 | 0.3069 | 0.7333 | 0.020* | |
C53 | 0.35057 (6) | 0.18097 (17) | 0.67222 (5) | 0.0248 (3) | |
H53 | 0.3295 | 0.1059 | 0.6896 | 0.030* | |
C38 | 0.61048 (6) | 0.2350 (2) | 0.92305 (5) | 0.0310 (3) | |
H38 | 0.6461 | 0.2311 | 0.9433 | 0.037* | |
C511 | 0.36840 (6) | 0.4486 (2) | 0.52261 (5) | 0.0298 (3) | |
H51A | 0.4095 | 0.4262 | 0.5222 | 0.045* | |
H51B | 0.3636 | 0.5585 | 0.5370 | 0.045* | |
H51C | 0.3487 | 0.4473 | 0.4897 | 0.045* | |
O61 | 0.22635 (4) | 0.40047 (11) | 0.13133 (3) | 0.01906 (19) | |
O64 | 0.07332 (4) | 0.32928 (14) | 0.18334 (3) | 0.0316 (2) | |
O63 | 0.01585 (4) | 0.29424 (13) | −0.11462 (3) | 0.0294 (2) | |
C63 | 0.12093 (5) | 0.39015 (15) | 0.11531 (4) | 0.0186 (3) | |
C70 | 0.22422 (5) | 0.40593 (15) | 0.17964 (5) | 0.0193 (3) | |
C62 | 0.17574 (5) | 0.46126 (15) | 0.10066 (4) | 0.0175 (2) | |
H62 | 0.1788 | 0.4219 | 0.0673 | 0.021* | |
C76 | 0.13695 (5) | 0.75279 (16) | 0.11604 (5) | 0.0208 (3) | |
H76 | 0.1035 | 0.7045 | 0.1263 | 0.025* | |
C77 | 0.07469 (5) | 0.34220 (15) | 0.08504 (5) | 0.0199 (3) | |
H77 | 0.0438 | 0.3011 | 0.1006 | 0.024* | |
C64 | 0.11821 (5) | 0.36726 (16) | 0.16759 (5) | 0.0207 (3) | |
C66 | 0.17394 (6) | 0.38554 (17) | 0.24932 (5) | 0.0242 (3) | |
H66 | 0.1391 | 0.3727 | 0.2631 | 0.029* | |
C75 | 0.14402 (6) | 0.92594 (17) | 0.11667 (5) | 0.0242 (3) | |
H75 | 0.1153 | 0.9953 | 0.1275 | 0.029* | |
C65 | 0.17270 (5) | 0.38931 (15) | 0.19937 (5) | 0.0196 (3) | |
C74 | 0.19253 (6) | 0.99728 (16) | 0.10159 (5) | 0.0245 (3) | |
H74 | 0.1972 | 1.1152 | 0.1023 | 0.029* | |
C73 | 0.23435 (6) | 0.89628 (17) | 0.08536 (5) | 0.0237 (3) | |
H73 | 0.2676 | 0.9450 | 0.0748 | 0.028* | |
C78 | 0.06315 (5) | 0.34154 (16) | 0.03287 (5) | 0.0201 (3) | |
C71 | 0.17897 (5) | 0.65101 (15) | 0.10037 (4) | 0.0179 (2) | |
C69 | 0.27641 (6) | 0.41947 (19) | 0.20914 (5) | 0.0278 (3) | |
H69 | 0.3115 | 0.4303 | 0.1956 | 0.033* | |
C83 | 0.01889 (6) | 0.23595 (17) | 0.01259 (5) | 0.0243 (3) | |
H83 | −0.0016 | 0.1715 | 0.0333 | 0.029* | |
C79 | 0.09117 (6) | 0.43776 (16) | 0.00123 (5) | 0.0226 (3) | |
H79 | 0.1207 | 0.5129 | 0.0137 | 0.027* | |
C72 | 0.22748 (5) | 0.72430 (16) | 0.08461 (5) | 0.0208 (3) | |
H72 | 0.2560 | 0.6555 | 0.0733 | 0.025* | |
C82 | 0.00403 (6) | 0.22232 (18) | −0.03621 (5) | 0.0261 (3) | |
H82 | −0.0259 | 0.1487 | −0.0488 | 0.031* | |
C80 | 0.07665 (6) | 0.42563 (17) | −0.04811 (5) | 0.0239 (3) | |
H80 | 0.0964 | 0.4915 | −0.0689 | 0.029* | |
C68 | 0.27653 (6) | 0.4169 (2) | 0.25813 (5) | 0.0343 (3) | |
H68 | 0.3120 | 0.4266 | 0.2784 | 0.041* | |
C811 | 0.04246 (6) | 0.3967 (2) | −0.14750 (5) | 0.0337 (3) | |
H81A | 0.0339 | 0.5144 | −0.1420 | 0.051* | |
H81B | 0.0275 | 0.3661 | −0.1805 | 0.051* | |
H81C | 0.0842 | 0.3794 | −0.1425 | 0.051* | |
C67 | 0.22546 (6) | 0.4003 (2) | 0.27861 (5) | 0.0314 (3) | |
H67 | 0.2262 | 0.3993 | 0.3125 | 0.038* | |
C81 | 0.03315 (6) | 0.31704 (17) | −0.06707 (5) | 0.0228 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0148 (4) | 0.0201 (4) | 0.0181 (4) | −0.0028 (3) | 0.0019 (3) | −0.0018 (3) |
O4 | 0.0196 (5) | 0.0398 (6) | 0.0227 (5) | 0.0045 (4) | 0.0063 (4) | 0.0012 (4) |
O3 | 0.0321 (5) | 0.0350 (5) | 0.0194 (5) | 0.0056 (4) | −0.0023 (4) | 0.0010 (4) |
C5 | 0.0205 (6) | 0.0170 (6) | 0.0211 (6) | −0.0014 (5) | 0.0033 (5) | 0.0018 (5) |
C4 | 0.0195 (6) | 0.0168 (6) | 0.0212 (6) | −0.0001 (5) | 0.0048 (5) | 0.0024 (5) |
C6 | 0.0235 (7) | 0.0295 (7) | 0.0221 (7) | −0.0030 (5) | 0.0051 (5) | 0.0015 (5) |
C3 | 0.0180 (6) | 0.0133 (5) | 0.0202 (6) | −0.0011 (5) | 0.0034 (5) | 0.0006 (5) |
C17 | 0.0172 (6) | 0.0157 (6) | 0.0233 (6) | 0.0006 (5) | 0.0044 (5) | −0.0010 (5) |
C21 | 0.0230 (6) | 0.0228 (6) | 0.0194 (6) | −0.0039 (5) | −0.0017 (5) | 0.0007 (5) |
C9 | 0.0177 (6) | 0.0333 (7) | 0.0248 (7) | −0.0030 (5) | 0.0024 (5) | 0.0004 (6) |
C19 | 0.0160 (6) | 0.0176 (6) | 0.0220 (6) | −0.0002 (5) | 0.0005 (5) | 0.0008 (5) |
C23 | 0.0195 (6) | 0.0241 (6) | 0.0246 (7) | 0.0034 (5) | 0.0005 (5) | −0.0023 (5) |
C18 | 0.0165 (6) | 0.0175 (6) | 0.0232 (6) | −0.0020 (5) | 0.0008 (5) | 0.0004 (5) |
C16 | 0.0197 (6) | 0.0207 (6) | 0.0238 (6) | −0.0002 (5) | 0.0029 (5) | −0.0011 (5) |
C2 | 0.0148 (6) | 0.0172 (6) | 0.0160 (6) | −0.0009 (5) | −0.0002 (4) | −0.0001 (4) |
C14 | 0.0316 (7) | 0.0158 (6) | 0.0265 (7) | 0.0016 (5) | −0.0029 (5) | −0.0006 (5) |
C15 | 0.0235 (7) | 0.0224 (7) | 0.0290 (7) | 0.0047 (5) | 0.0012 (5) | −0.0035 (5) |
C10 | 0.0217 (6) | 0.0161 (6) | 0.0178 (6) | −0.0021 (5) | 0.0035 (5) | 0.0015 (5) |
C11 | 0.0176 (6) | 0.0180 (6) | 0.0153 (6) | 0.0010 (5) | −0.0016 (4) | 0.0001 (5) |
C12 | 0.0201 (6) | 0.0197 (6) | 0.0180 (6) | −0.0013 (5) | 0.0009 (5) | −0.0004 (5) |
C20 | 0.0193 (6) | 0.0198 (6) | 0.0217 (6) | −0.0024 (5) | 0.0032 (5) | −0.0008 (5) |
C13 | 0.0285 (7) | 0.0195 (6) | 0.0221 (6) | −0.0040 (5) | 0.0005 (5) | 0.0023 (5) |
C8 | 0.0233 (7) | 0.0474 (9) | 0.0232 (7) | −0.0053 (6) | −0.0024 (5) | 0.0018 (6) |
C22 | 0.0219 (6) | 0.0256 (7) | 0.0266 (7) | 0.0052 (5) | −0.0023 (5) | 0.0013 (5) |
C7 | 0.0299 (7) | 0.0441 (8) | 0.0177 (6) | −0.0063 (6) | 0.0013 (5) | 0.0012 (6) |
C211 | 0.0318 (7) | 0.0444 (9) | 0.0197 (7) | 0.0020 (7) | 0.0012 (5) | −0.0018 (6) |
O31 | 0.0153 (4) | 0.0193 (4) | 0.0186 (4) | 0.0028 (3) | 0.0028 (3) | 0.0012 (3) |
O34 | 0.0194 (5) | 0.0377 (5) | 0.0231 (5) | −0.0037 (4) | 0.0069 (4) | 0.0002 (4) |
C40 | 0.0219 (6) | 0.0154 (6) | 0.0185 (6) | 0.0019 (5) | 0.0035 (5) | −0.0017 (5) |
O33 | 0.0304 (5) | 0.0389 (6) | 0.0217 (5) | −0.0076 (4) | −0.0052 (4) | 0.0028 (4) |
C41 | 0.0184 (6) | 0.0182 (6) | 0.0147 (5) | −0.0008 (5) | −0.0018 (4) | −0.0005 (5) |
C42 | 0.0234 (6) | 0.0201 (6) | 0.0184 (6) | 0.0018 (5) | −0.0002 (5) | −0.0004 (5) |
C33 | 0.0181 (6) | 0.0141 (5) | 0.0206 (6) | 0.0010 (5) | 0.0043 (5) | −0.0014 (5) |
C46 | 0.0210 (6) | 0.0219 (6) | 0.0251 (6) | −0.0016 (5) | 0.0013 (5) | 0.0010 (5) |
C48 | 0.0162 (6) | 0.0197 (6) | 0.0222 (6) | 0.0006 (5) | 0.0020 (5) | −0.0019 (5) |
C36 | 0.0236 (7) | 0.0304 (7) | 0.0201 (6) | 0.0027 (5) | 0.0059 (5) | −0.0010 (5) |
C47 | 0.0180 (6) | 0.0168 (6) | 0.0235 (6) | −0.0008 (5) | 0.0050 (5) | −0.0006 (5) |
C52 | 0.0226 (6) | 0.0297 (7) | 0.0283 (7) | −0.0068 (6) | −0.0029 (5) | −0.0007 (6) |
C35 | 0.0201 (6) | 0.0176 (6) | 0.0214 (6) | 0.0006 (5) | 0.0038 (5) | −0.0014 (5) |
C43 | 0.0361 (8) | 0.0201 (6) | 0.0227 (7) | 0.0062 (6) | −0.0013 (5) | −0.0021 (5) |
C34 | 0.0195 (6) | 0.0165 (6) | 0.0219 (6) | 0.0004 (5) | 0.0049 (5) | −0.0029 (5) |
C45 | 0.0283 (7) | 0.0238 (7) | 0.0303 (7) | −0.0072 (6) | −0.0014 (5) | 0.0051 (6) |
C37 | 0.0293 (7) | 0.0443 (9) | 0.0177 (6) | 0.0058 (6) | 0.0022 (5) | −0.0009 (6) |
C51 | 0.0211 (6) | 0.0243 (6) | 0.0206 (6) | 0.0031 (5) | −0.0010 (5) | −0.0014 (5) |
C50 | 0.0183 (6) | 0.0192 (6) | 0.0227 (6) | 0.0018 (5) | 0.0034 (5) | 0.0006 (5) |
C44 | 0.0411 (8) | 0.0171 (6) | 0.0266 (7) | −0.0035 (6) | −0.0065 (6) | 0.0005 (5) |
C49 | 0.0163 (6) | 0.0193 (6) | 0.0222 (6) | 0.0001 (5) | 0.0003 (5) | −0.0021 (5) |
C39 | 0.0175 (6) | 0.0325 (7) | 0.0258 (7) | 0.0033 (5) | 0.0033 (5) | −0.0013 (6) |
C32 | 0.0152 (6) | 0.0178 (6) | 0.0167 (6) | 0.0011 (5) | 0.0015 (4) | −0.0003 (5) |
C53 | 0.0209 (6) | 0.0265 (7) | 0.0264 (7) | −0.0045 (5) | 0.0001 (5) | 0.0027 (5) |
C38 | 0.0218 (7) | 0.0453 (9) | 0.0245 (7) | 0.0047 (6) | −0.0023 (5) | −0.0015 (6) |
C511 | 0.0240 (7) | 0.0426 (8) | 0.0220 (7) | −0.0002 (6) | 0.0003 (5) | 0.0053 (6) |
O61 | 0.0178 (4) | 0.0199 (4) | 0.0201 (4) | 0.0030 (3) | 0.0051 (3) | 0.0015 (3) |
O64 | 0.0210 (5) | 0.0501 (6) | 0.0242 (5) | −0.0092 (4) | 0.0054 (4) | 0.0043 (5) |
O63 | 0.0277 (5) | 0.0389 (6) | 0.0208 (5) | −0.0022 (4) | −0.0005 (4) | −0.0014 (4) |
C63 | 0.0205 (6) | 0.0139 (5) | 0.0219 (6) | 0.0001 (5) | 0.0044 (5) | 0.0010 (5) |
C70 | 0.0220 (6) | 0.0153 (6) | 0.0210 (6) | 0.0019 (5) | 0.0041 (5) | 0.0010 (5) |
C62 | 0.0179 (6) | 0.0175 (6) | 0.0173 (6) | 0.0008 (5) | 0.0028 (4) | 0.0006 (5) |
C76 | 0.0209 (6) | 0.0213 (6) | 0.0202 (6) | −0.0002 (5) | 0.0027 (5) | 0.0004 (5) |
C77 | 0.0193 (6) | 0.0175 (6) | 0.0235 (6) | −0.0004 (5) | 0.0051 (5) | 0.0012 (5) |
C64 | 0.0211 (6) | 0.0191 (6) | 0.0224 (6) | −0.0015 (5) | 0.0049 (5) | 0.0011 (5) |
C66 | 0.0224 (6) | 0.0279 (7) | 0.0233 (7) | −0.0007 (5) | 0.0061 (5) | 0.0029 (5) |
C75 | 0.0281 (7) | 0.0203 (6) | 0.0237 (6) | 0.0050 (5) | 0.0015 (5) | −0.0017 (5) |
C65 | 0.0203 (6) | 0.0160 (6) | 0.0228 (6) | 0.0004 (5) | 0.0040 (5) | 0.0013 (5) |
C74 | 0.0316 (7) | 0.0157 (6) | 0.0243 (6) | −0.0016 (5) | −0.0041 (5) | 0.0006 (5) |
C73 | 0.0230 (6) | 0.0218 (6) | 0.0255 (7) | −0.0058 (5) | −0.0009 (5) | 0.0038 (5) |
C78 | 0.0186 (6) | 0.0176 (6) | 0.0239 (6) | 0.0016 (5) | 0.0025 (5) | −0.0003 (5) |
C71 | 0.0200 (6) | 0.0179 (6) | 0.0151 (6) | −0.0019 (5) | 0.0001 (4) | 0.0003 (5) |
C69 | 0.0188 (6) | 0.0368 (8) | 0.0280 (7) | 0.0006 (6) | 0.0038 (5) | 0.0043 (6) |
C83 | 0.0206 (6) | 0.0253 (7) | 0.0267 (7) | −0.0034 (5) | 0.0020 (5) | 0.0033 (5) |
C79 | 0.0235 (6) | 0.0193 (6) | 0.0243 (6) | −0.0030 (5) | 0.0008 (5) | 0.0006 (5) |
C72 | 0.0202 (6) | 0.0207 (6) | 0.0215 (6) | −0.0003 (5) | 0.0022 (5) | 0.0007 (5) |
C82 | 0.0215 (6) | 0.0286 (7) | 0.0269 (7) | −0.0043 (5) | −0.0021 (5) | −0.0007 (6) |
C80 | 0.0247 (7) | 0.0233 (6) | 0.0237 (7) | −0.0010 (5) | 0.0033 (5) | 0.0027 (5) |
C68 | 0.0210 (7) | 0.0527 (10) | 0.0277 (7) | −0.0027 (6) | −0.0026 (5) | 0.0051 (7) |
C811 | 0.0291 (7) | 0.0505 (9) | 0.0214 (7) | −0.0002 (7) | 0.0030 (5) | 0.0030 (6) |
C67 | 0.0279 (7) | 0.0454 (8) | 0.0208 (7) | −0.0024 (6) | 0.0020 (5) | 0.0048 (6) |
C81 | 0.0220 (6) | 0.0243 (6) | 0.0215 (6) | 0.0043 (5) | 0.0000 (5) | −0.0004 (5) |
O1—C10 | 1.3623 (15) | C52—C53 | 1.374 (2) |
O1—C2 | 1.4600 (14) | C52—C51 | 1.398 (2) |
O4—C4 | 1.2287 (16) | C52—H52 | 0.9500 |
O3—C21 | 1.3565 (16) | C35—C34 | 1.4730 (17) |
O3—C211 | 1.4308 (18) | C43—C44 | 1.383 (2) |
C5—C10 | 1.4000 (18) | C43—H43 | 0.9500 |
C5—C6 | 1.4038 (19) | C45—C44 | 1.391 (2) |
C5—C4 | 1.4717 (17) | C45—H45 | 0.9500 |
C4—C3 | 1.4941 (17) | C37—C38 | 1.400 (2) |
C6—C7 | 1.3786 (19) | C37—H37 | 0.9500 |
C6—H6 | 0.9500 | C51—C50 | 1.3959 (18) |
C3—C17 | 1.3451 (18) | C50—C49 | 1.3952 (18) |
C3—C2 | 1.5052 (16) | C50—H50 | 0.9500 |
C17—C18 | 1.4597 (18) | C44—H44 | 0.9500 |
C17—H17 | 0.9500 | C49—H49 | 0.9500 |
C21—C22 | 1.395 (2) | C39—C38 | 1.379 (2) |
C21—C20 | 1.3983 (18) | C39—H39 | 0.9500 |
C9—C8 | 1.383 (2) | C32—H32 | 1.0000 |
C9—C10 | 1.3923 (18) | C53—H53 | 0.9500 |
C9—H9 | 0.9500 | C38—H38 | 0.9500 |
C19—C20 | 1.3919 (18) | C511—H51A | 0.9800 |
C19—C18 | 1.4007 (18) | C511—H51B | 0.9800 |
C19—H19 | 0.9500 | C511—H51C | 0.9800 |
C23—C22 | 1.3778 (19) | O61—C70 | 1.3656 (16) |
C23—C18 | 1.4082 (18) | O61—C62 | 1.4592 (14) |
C23—H23 | 0.9500 | O64—C64 | 1.2284 (16) |
C16—C15 | 1.3910 (19) | O63—C81 | 1.3597 (16) |
C16—C11 | 1.3946 (18) | O63—C811 | 1.4345 (18) |
C16—H16 | 0.9500 | C63—C77 | 1.3466 (18) |
C2—C11 | 1.5218 (17) | C63—C64 | 1.4902 (18) |
C2—H2 | 1.0000 | C63—C62 | 1.5072 (17) |
C14—C15 | 1.387 (2) | C70—C69 | 1.3927 (19) |
C14—C13 | 1.389 (2) | C70—C65 | 1.3953 (18) |
C14—H14 | 0.9500 | C62—C71 | 1.5205 (17) |
C15—H15 | 0.9500 | C62—H62 | 1.0000 |
C11—C12 | 1.3902 (18) | C76—C71 | 1.3904 (18) |
C12—C13 | 1.3953 (19) | C76—C75 | 1.3954 (19) |
C12—H12 | 0.9500 | C76—H76 | 0.9500 |
C20—H20 | 0.9500 | C77—C78 | 1.4576 (18) |
C13—H13 | 0.9500 | C77—H77 | 0.9500 |
C8—C7 | 1.396 (2) | C64—C65 | 1.4738 (18) |
C8—H8 | 0.9500 | C66—C67 | 1.378 (2) |
C22—H22 | 0.9500 | C66—C65 | 1.4013 (19) |
C7—H7 | 0.9500 | C66—H66 | 0.9500 |
C211—H21A | 0.9800 | C75—C74 | 1.384 (2) |
C211—H21B | 0.9800 | C75—H75 | 0.9500 |
C211—H21C | 0.9800 | C74—C73 | 1.390 (2) |
O31—C40 | 1.3631 (15) | C74—H74 | 0.9500 |
O31—C32 | 1.4584 (14) | C73—C72 | 1.3855 (19) |
O34—C34 | 1.2299 (16) | C73—H73 | 0.9500 |
C40—C39 | 1.3948 (18) | C78—C79 | 1.3998 (18) |
C40—C35 | 1.3970 (18) | C78—C83 | 1.4020 (19) |
O33—C51 | 1.3572 (16) | C71—C72 | 1.3982 (18) |
O33—C511 | 1.4271 (18) | C69—C68 | 1.377 (2) |
C41—C42 | 1.3900 (18) | C69—H69 | 0.9500 |
C41—C46 | 1.3953 (18) | C83—C82 | 1.377 (2) |
C41—C32 | 1.5174 (17) | C83—H83 | 0.9500 |
C42—C43 | 1.3939 (19) | C79—C80 | 1.3896 (19) |
C42—H42 | 0.9500 | C79—H79 | 0.9500 |
C33—C47 | 1.3453 (18) | C72—H72 | 0.9500 |
C33—C34 | 1.4918 (17) | C82—C81 | 1.393 (2) |
C33—C32 | 1.5057 (16) | C82—H82 | 0.9500 |
C46—C45 | 1.384 (2) | C80—C81 | 1.3932 (19) |
C46—H46 | 0.9500 | C80—H80 | 0.9500 |
C48—C49 | 1.3998 (18) | C68—C67 | 1.397 (2) |
C48—C53 | 1.4061 (18) | C68—H68 | 0.9500 |
C48—C47 | 1.4619 (18) | C811—H81A | 0.9800 |
C36—C37 | 1.3779 (19) | C811—H81B | 0.9800 |
C36—C35 | 1.4051 (18) | C811—H81C | 0.9800 |
C36—H36 | 0.9500 | C67—H67 | 0.9500 |
C47—H47 | 0.9500 | ||
C10—O1—C2 | 117.97 (9) | C46—C45—H45 | 120.1 |
C21—O3—C211 | 117.40 (11) | C44—C45—H45 | 120.1 |
C10—C5—C6 | 118.91 (12) | C36—C37—C38 | 119.56 (13) |
C10—C5—C4 | 120.07 (11) | C36—C37—H37 | 120.2 |
C6—C5—C4 | 120.90 (12) | C38—C37—H37 | 120.2 |
O4—C4—C5 | 121.84 (12) | O33—C51—C50 | 125.32 (12) |
O4—C4—C3 | 122.08 (11) | O33—C51—C52 | 115.40 (12) |
C5—C4—C3 | 116.05 (11) | C50—C51—C52 | 119.28 (12) |
C7—C6—C5 | 120.50 (13) | C49—C50—C51 | 119.85 (12) |
C7—C6—H6 | 119.8 | C49—C50—H50 | 120.1 |
C5—C6—H6 | 119.8 | C51—C50—H50 | 120.1 |
C17—C3—C4 | 117.37 (11) | C43—C44—C45 | 120.09 (13) |
C17—C3—C2 | 125.02 (11) | C43—C44—H44 | 120.0 |
C4—C3—C2 | 117.61 (10) | C45—C44—H44 | 120.0 |
C3—C17—C18 | 132.39 (11) | C50—C49—C48 | 121.62 (12) |
C3—C17—H17 | 113.8 | C50—C49—H49 | 119.2 |
C18—C17—H17 | 113.8 | C48—C49—H49 | 119.2 |
O3—C21—C22 | 115.51 (12) | C38—C39—C40 | 119.20 (12) |
O3—C21—C20 | 125.13 (12) | C38—C39—H39 | 120.4 |
C22—C21—C20 | 119.35 (12) | C40—C39—H39 | 120.4 |
C8—C9—C10 | 119.21 (12) | O31—C32—C33 | 112.68 (10) |
C8—C9—H9 | 120.4 | O31—C32—C41 | 107.63 (9) |
C10—C9—H9 | 120.4 | C33—C32—C41 | 114.85 (10) |
C20—C19—C18 | 121.50 (11) | O31—C32—H32 | 107.1 |
C20—C19—H19 | 119.2 | C33—C32—H32 | 107.1 |
C18—C19—H19 | 119.2 | C41—C32—H32 | 107.1 |
C22—C23—C18 | 122.06 (12) | C52—C53—C48 | 122.15 (13) |
C22—C23—H23 | 119.0 | C52—C53—H53 | 118.9 |
C18—C23—H23 | 119.0 | C48—C53—H53 | 118.9 |
C19—C18—C23 | 117.07 (12) | C39—C38—C37 | 121.05 (12) |
C19—C18—C17 | 126.57 (11) | C39—C38—H38 | 119.5 |
C23—C18—C17 | 116.33 (11) | C37—C38—H38 | 119.5 |
C15—C16—C11 | 120.38 (12) | O33—C511—H51A | 109.5 |
C15—C16—H16 | 119.8 | O33—C511—H51B | 109.5 |
C11—C16—H16 | 119.8 | H51A—C511—H51B | 109.5 |
O1—C2—C3 | 112.32 (9) | O33—C511—H51C | 109.5 |
O1—C2—C11 | 107.50 (9) | H51A—C511—H51C | 109.5 |
C3—C2—C11 | 114.82 (10) | H51B—C511—H51C | 109.5 |
O1—C2—H2 | 107.3 | C70—O61—C62 | 116.70 (9) |
C3—C2—H2 | 107.3 | C81—O63—C811 | 117.16 (11) |
C11—C2—H2 | 107.3 | C77—C63—C64 | 117.28 (11) |
C15—C14—C13 | 120.21 (12) | C77—C63—C62 | 125.43 (11) |
C15—C14—H14 | 119.9 | C64—C63—C62 | 117.27 (11) |
C13—C14—H14 | 119.9 | O61—C70—C69 | 117.16 (11) |
C14—C15—C16 | 119.80 (13) | O61—C70—C65 | 122.19 (11) |
C14—C15—H15 | 120.1 | C69—C70—C65 | 120.56 (12) |
C16—C15—H15 | 120.1 | O61—C62—C63 | 111.65 (10) |
O1—C10—C9 | 116.44 (11) | O61—C62—C71 | 107.38 (10) |
O1—C10—C5 | 122.73 (11) | C63—C62—C71 | 115.04 (10) |
C9—C10—C5 | 120.74 (12) | O61—C62—H62 | 107.5 |
C12—C11—C16 | 119.55 (12) | C63—C62—H62 | 107.5 |
C12—C11—C2 | 122.99 (11) | C71—C62—H62 | 107.5 |
C16—C11—C2 | 117.45 (11) | C71—C76—C75 | 119.88 (12) |
C11—C12—C13 | 120.08 (12) | C71—C76—H76 | 120.1 |
C11—C12—H12 | 120.0 | C75—C76—H76 | 120.1 |
C13—C12—H12 | 120.0 | C63—C77—C78 | 132.10 (12) |
C19—C20—C21 | 120.00 (12) | C63—C77—H77 | 114.0 |
C19—C20—H20 | 120.0 | C78—C77—H77 | 114.0 |
C21—C20—H20 | 120.0 | O64—C64—C65 | 121.73 (12) |
C14—C13—C12 | 119.96 (13) | O64—C64—C63 | 121.96 (12) |
C14—C13—H13 | 120.0 | C65—C64—C63 | 116.29 (11) |
C12—C13—H13 | 120.0 | C67—C66—C65 | 120.28 (12) |
C9—C8—C7 | 120.96 (13) | C67—C66—H66 | 119.9 |
C9—C8—H8 | 119.5 | C65—C66—H66 | 119.9 |
C7—C8—H8 | 119.5 | C74—C75—C76 | 120.42 (13) |
C23—C22—C21 | 120.01 (12) | C74—C75—H75 | 119.8 |
C23—C22—H22 | 120.0 | C76—C75—H75 | 119.8 |
C21—C22—H22 | 120.0 | C70—C65—C66 | 119.30 (12) |
C6—C7—C8 | 119.69 (13) | C70—C65—C64 | 119.75 (11) |
C6—C7—H7 | 120.2 | C66—C65—C64 | 120.87 (11) |
C8—C7—H7 | 120.2 | C75—C74—C73 | 119.94 (12) |
O3—C211—H21A | 109.5 | C75—C74—H74 | 120.0 |
O3—C211—H21B | 109.5 | C73—C74—H74 | 120.0 |
H21A—C211—H21B | 109.5 | C72—C73—C74 | 119.84 (12) |
O3—C211—H21C | 109.5 | C72—C73—H73 | 120.1 |
H21A—C211—H21C | 109.5 | C74—C73—H73 | 120.1 |
H21B—C211—H21C | 109.5 | C79—C78—C83 | 117.02 (12) |
C40—O31—C32 | 117.69 (9) | C79—C78—C77 | 126.46 (12) |
O31—C40—C39 | 116.48 (11) | C83—C78—C77 | 116.50 (11) |
O31—C40—C35 | 122.69 (11) | C76—C71—C72 | 119.30 (12) |
C39—C40—C35 | 120.73 (12) | C76—C71—C62 | 123.07 (11) |
C51—O33—C511 | 118.08 (11) | C72—C71—C62 | 117.61 (11) |
C42—C41—C46 | 119.40 (12) | C68—C69—C70 | 119.13 (13) |
C42—C41—C32 | 123.58 (12) | C68—C69—H69 | 120.4 |
C46—C41—C32 | 117.02 (11) | C70—C69—H69 | 120.4 |
C41—C42—C43 | 120.03 (13) | C82—C83—C78 | 122.35 (12) |
C41—C42—H42 | 120.0 | C82—C83—H83 | 118.8 |
C43—C42—H42 | 120.0 | C78—C83—H83 | 118.8 |
C47—C33—C34 | 118.04 (11) | C80—C79—C78 | 121.33 (12) |
C47—C33—C32 | 124.20 (11) | C80—C79—H79 | 119.3 |
C34—C33—C32 | 117.76 (10) | C78—C79—H79 | 119.3 |
C45—C46—C41 | 120.51 (13) | C73—C72—C71 | 120.60 (12) |
C45—C46—H46 | 119.7 | C73—C72—H72 | 119.7 |
C41—C46—H46 | 119.7 | C71—C72—H72 | 119.7 |
C49—C48—C53 | 117.00 (12) | C83—C82—C81 | 119.67 (12) |
C49—C48—C47 | 126.19 (11) | C83—C82—H82 | 120.2 |
C53—C48—C47 | 116.77 (11) | C81—C82—H82 | 120.2 |
C37—C36—C35 | 120.48 (12) | C79—C80—C81 | 120.11 (12) |
C37—C36—H36 | 119.8 | C79—C80—H80 | 119.9 |
C35—C36—H36 | 119.8 | C81—C80—H80 | 119.9 |
C33—C47—C48 | 131.28 (12) | C69—C68—C67 | 121.23 (13) |
C33—C47—H47 | 114.4 | C69—C68—H68 | 119.4 |
C48—C47—H47 | 114.4 | C67—C68—H68 | 119.4 |
C53—C52—C51 | 120.09 (12) | O63—C811—H81A | 109.5 |
C53—C52—H52 | 120.0 | O63—C811—H81B | 109.5 |
C51—C52—H52 | 120.0 | H81A—C811—H81B | 109.5 |
C40—C35—C36 | 118.98 (12) | O63—C811—H81C | 109.5 |
C40—C35—C34 | 120.14 (11) | H81A—C811—H81C | 109.5 |
C36—C35—C34 | 120.78 (11) | H81B—C811—H81C | 109.5 |
C44—C43—C42 | 120.14 (13) | C66—C67—C68 | 119.50 (13) |
C44—C43—H43 | 119.9 | C66—C67—H67 | 120.3 |
C42—C43—H43 | 119.9 | C68—C67—H67 | 120.3 |
O34—C34—C35 | 121.95 (12) | O63—C81—C82 | 115.48 (12) |
O34—C34—C33 | 121.99 (11) | O63—C81—C80 | 125.02 (12) |
C35—C34—C33 | 116.04 (11) | C82—C81—C80 | 119.50 (12) |
C46—C45—C44 | 119.82 (13) | ||
C10—C5—C4—O4 | 172.55 (12) | C511—O33—C51—C52 | 172.73 (12) |
C6—C5—C4—O4 | −3.4 (2) | C53—C52—C51—O33 | −177.89 (13) |
C10—C5—C4—C3 | −5.40 (17) | C53—C52—C51—C50 | 1.6 (2) |
C6—C5—C4—C3 | 178.69 (11) | O33—C51—C50—C49 | 177.97 (12) |
C10—C5—C6—C7 | −0.1 (2) | C52—C51—C50—C49 | −1.43 (19) |
C4—C5—C6—C7 | 175.82 (13) | C42—C43—C44—C45 | 0.6 (2) |
O4—C4—C3—C17 | −12.43 (18) | C46—C45—C44—C43 | −0.5 (2) |
C5—C4—C3—C17 | 165.51 (11) | C51—C50—C49—C48 | 0.45 (19) |
O4—C4—C3—C2 | 168.13 (12) | C53—C48—C49—C50 | 0.38 (18) |
C5—C4—C3—C2 | −13.93 (16) | C47—C48—C49—C50 | −177.01 (12) |
C4—C3—C17—C18 | −179.20 (12) | O31—C40—C39—C38 | −176.80 (12) |
C2—C3—C17—C18 | 0.2 (2) | C35—C40—C39—C38 | −0.4 (2) |
C211—O3—C21—C22 | 173.76 (12) | C40—O31—C32—C33 | −42.30 (14) |
C211—O3—C21—C20 | −6.13 (19) | C40—O31—C32—C41 | 85.35 (12) |
C20—C19—C18—C23 | −0.82 (18) | C47—C33—C32—O31 | −145.24 (12) |
C20—C19—C18—C17 | −178.53 (12) | C34—C33—C32—O31 | 34.79 (14) |
C22—C23—C18—C19 | 0.60 (19) | C47—C33—C32—C41 | 91.03 (15) |
C22—C23—C18—C17 | 178.55 (12) | C34—C33—C32—C41 | −88.94 (13) |
C3—C17—C18—C19 | −18.2 (2) | C42—C41—C32—O31 | −117.82 (12) |
C3—C17—C18—C23 | 164.12 (13) | C46—C41—C32—O31 | 62.14 (14) |
C10—O1—C2—C3 | −42.24 (14) | C42—C41—C32—C33 | 8.55 (17) |
C10—O1—C2—C11 | 85.01 (12) | C46—C41—C32—C33 | −171.49 (11) |
C17—C3—C2—O1 | −142.84 (12) | C51—C52—C53—C48 | −0.7 (2) |
C4—C3—C2—O1 | 36.55 (14) | C49—C48—C53—C52 | −0.2 (2) |
C17—C3—C2—C11 | 93.93 (14) | C47—C48—C53—C52 | 177.40 (13) |
C4—C3—C2—C11 | −86.68 (13) | C40—C39—C38—C37 | 0.0 (2) |
C13—C14—C15—C16 | −0.7 (2) | C36—C37—C38—C39 | 0.2 (2) |
C11—C16—C15—C14 | −0.1 (2) | C62—O61—C70—C69 | −153.01 (11) |
C2—O1—C10—C9 | −158.52 (11) | C62—O61—C70—C65 | 30.56 (16) |
C2—O1—C10—C5 | 24.89 (16) | C70—O61—C62—C63 | −47.30 (13) |
C8—C9—C10—O1 | −176.47 (12) | C70—O61—C62—C71 | 79.67 (12) |
C8—C9—C10—C5 | 0.2 (2) | C77—C63—C62—O61 | −141.66 (12) |
C6—C5—C10—O1 | 176.38 (11) | C64—C63—C62—O61 | 36.81 (14) |
C4—C5—C10—O1 | 0.38 (18) | C77—C63—C62—C71 | 95.64 (15) |
C6—C5—C10—C9 | −0.07 (19) | C64—C63—C62—C71 | −85.89 (13) |
C4—C5—C10—C9 | −176.07 (12) | C64—C63—C77—C78 | −177.96 (12) |
C15—C16—C11—C12 | 0.72 (19) | C62—C63—C77—C78 | 0.5 (2) |
C15—C16—C11—C2 | −177.83 (12) | C77—C63—C64—O64 | −10.26 (19) |
O1—C2—C11—C12 | −114.83 (12) | C62—C63—C64—O64 | 171.15 (12) |
C3—C2—C11—C12 | 10.94 (17) | C77—C63—C64—C65 | 168.52 (11) |
O1—C2—C11—C16 | 63.66 (14) | C62—C63—C64—C65 | −10.07 (16) |
C3—C2—C11—C16 | −170.57 (10) | C71—C76—C75—C74 | 0.3 (2) |
C16—C11—C12—C13 | −0.59 (18) | O61—C70—C65—C66 | 176.02 (11) |
C2—C11—C12—C13 | 177.87 (11) | C69—C70—C65—C66 | −0.30 (19) |
C18—C19—C20—C21 | 0.85 (19) | O61—C70—C65—C64 | −0.83 (18) |
O3—C21—C20—C19 | 179.27 (12) | C69—C70—C65—C64 | −177.15 (12) |
C22—C21—C20—C19 | −0.62 (19) | C67—C66—C65—C70 | 0.9 (2) |
C15—C14—C13—C12 | 0.8 (2) | C67—C66—C65—C64 | 177.67 (13) |
C11—C12—C13—C14 | −0.16 (19) | O64—C64—C65—C70 | 169.77 (13) |
C10—C9—C8—C7 | −0.1 (2) | C63—C64—C65—C70 | −9.01 (17) |
C18—C23—C22—C21 | −0.4 (2) | O64—C64—C65—C66 | −7.0 (2) |
O3—C21—C22—C23 | −179.49 (12) | C63—C64—C65—C66 | 174.19 (11) |
C20—C21—C22—C23 | 0.4 (2) | C76—C75—C74—C73 | 0.5 (2) |
C5—C6—C7—C8 | 0.2 (2) | C75—C74—C73—C72 | −0.4 (2) |
C9—C8—C7—C6 | −0.1 (2) | C63—C77—C78—C79 | −21.0 (2) |
C32—O31—C40—C39 | −157.69 (11) | C63—C77—C78—C83 | 160.18 (14) |
C32—O31—C40—C35 | 25.97 (16) | C75—C76—C71—C72 | −1.11 (19) |
C46—C41—C42—C43 | −0.85 (18) | C75—C76—C71—C62 | 177.25 (12) |
C32—C41—C42—C43 | 179.11 (12) | O61—C62—C71—C76 | −119.98 (12) |
C42—C41—C46—C45 | 1.01 (19) | C63—C62—C71—C76 | 4.98 (17) |
C32—C41—C46—C45 | −178.95 (12) | O61—C62—C71—C72 | 58.40 (14) |
C34—C33—C47—C48 | 177.83 (12) | C63—C62—C71—C72 | −176.64 (11) |
C32—C33—C47—C48 | −2.1 (2) | O61—C70—C69—C68 | −176.75 (13) |
C49—C48—C47—C33 | −20.9 (2) | C65—C70—C69—C68 | −0.3 (2) |
C53—C48—C47—C33 | 161.75 (14) | C79—C78—C83—C82 | 1.7 (2) |
O31—C40—C35—C36 | 176.70 (11) | C77—C78—C83—C82 | −179.34 (12) |
C39—C40—C35—C36 | 0.51 (19) | C83—C78—C79—C80 | −1.62 (19) |
O31—C40—C35—C34 | 0.11 (19) | C77—C78—C79—C80 | 179.56 (12) |
C39—C40—C35—C34 | −176.08 (12) | C74—C73—C72—C71 | −0.5 (2) |
C37—C36—C35—C40 | −0.3 (2) | C76—C71—C72—C73 | 1.22 (19) |
C37—C36—C35—C34 | 176.28 (13) | C62—C71—C72—C73 | −177.23 (12) |
C41—C42—C43—C44 | 0.0 (2) | C78—C83—C82—C81 | −0.6 (2) |
C40—C35—C34—O34 | 171.68 (12) | C78—C79—C80—C81 | 0.5 (2) |
C36—C35—C34—O34 | −4.8 (2) | C70—C69—C68—C67 | 0.3 (2) |
C40—C35—C34—C33 | −7.01 (17) | C65—C66—C67—C68 | −0.8 (2) |
C36—C35—C34—C33 | 176.46 (11) | C69—C68—C67—C66 | 0.3 (3) |
C47—C33—C34—O34 | −9.97 (18) | C811—O63—C81—C82 | 176.45 (12) |
C32—C33—C34—O34 | 170.01 (12) | C811—O63—C81—C80 | −3.50 (19) |
C47—C33—C34—C35 | 168.73 (11) | C83—C82—C81—O63 | 179.47 (12) |
C32—C33—C34—C35 | −11.30 (16) | C83—C82—C81—C80 | −0.6 (2) |
C41—C46—C45—C44 | −0.4 (2) | C79—C80—C81—O63 | −179.39 (12) |
C35—C36—C37—C38 | 0.0 (2) | C79—C80—C81—C82 | 0.7 (2) |
C511—O33—C51—C50 | −6.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O34i | 1.00 | 2.45 | 3.3434 (15) | 148 |
C6—H6···O61ii | 0.95 | 2.40 | 3.2676 (16) | 151 |
C14—H14···O1iii | 0.95 | 2.46 | 3.3750 (15) | 161 |
C32—H32···O64iv | 1.00 | 2.37 | 3.2348 (15) | 144 |
C36—H36···O1v | 0.95 | 2.42 | 3.2733 (15) | 150 |
C44—H44···O31iii | 0.95 | 2.42 | 3.3399 (16) | 162 |
C62—H62···O4vi | 1.00 | 2.48 | 3.3629 (15) | 146 |
C66—H66···O31vii | 0.95 | 2.48 | 3.3725 (15) | 157 |
C74—H74···O61iii | 0.95 | 2.49 | 3.4018 (15) | 161 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x, y+1, z; (iv) x+1/2, −y+1/2, z+1/2; (v) −x+1/2, y−1/2, −z+3/2; (vi) −x+1/2, y−1/2, −z+1/2; (vii) x−1/2, −y+1/2, z−1/2. |
C16H12O2 | Z = 2 |
Mr = 236.26 | F(000) = 248 |
Triclinic, P1 | Dx = 1.347 Mg m−3 |
a = 7.7718 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.6069 (3) Å | Cell parameters from 3741 reflections |
c = 9.0857 (3) Å | θ = 3.7–35.8° |
α = 89.744 (3)° | µ = 0.09 mm−1 |
β = 84.862 (3)° | T = 100 K |
γ = 74.199 (3)° | Needle, colorless |
V = 582.31 (4) Å3 | 0.18 × 0.08 × 0.08 mm |
Rigaku OD SuperNova Dual source diffractometer with an Atlas detector | 2425 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source | 2120 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.023 |
Detector resolution: 10.4498 pixels mm-1 | θmax = 26.5°, θmin = 3.3° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −9→10 |
Tmin = 0.865, Tmax = 1.000 | l = −11→11 |
4947 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0597P)2 + 0.1583P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2425 reflections | Δρmax = 0.29 e Å−3 |
163 parameters | Δρmin = −0.22 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 | ||
O1 | 0.56491 (12) | 0.96012 (10) | 0.67017 (9) | 0.0203 (2) | |
O4 | 0.31184 (12) | 0.69758 (10) | 0.94932 (9) | 0.0221 (2) | |
C9 | 0.43926 (16) | 1.03656 (15) | 0.78021 (13) | 0.0174 (3) | |
C4 | 0.38354 (17) | 0.77597 (15) | 0.86245 (13) | 0.0175 (3) | |
C12 | 0.74274 (17) | 0.43694 (14) | 0.64267 (13) | 0.0182 (3) | |
C3 | 0.52016 (17) | 0.69819 (15) | 0.73982 (13) | 0.0172 (3) | |
C10 | 0.34234 (16) | 0.95369 (14) | 0.87368 (13) | 0.0177 (3) | |
C8 | 0.41493 (18) | 1.20162 (15) | 0.79971 (14) | 0.0208 (3) | |
H8 | 0.4843 | 1.2560 | 0.7383 | 0.025* | |
C11 | 0.60958 (17) | 0.54181 (15) | 0.74961 (13) | 0.0181 (3) | |
H11 | 0.5826 | 0.4918 | 0.8389 | 0.022* | |
C5 | 0.21682 (17) | 1.04169 (16) | 0.98441 (14) | 0.0207 (3) | |
H5 | 0.1504 | 0.9873 | 1.0488 | 0.025* | |
C13 | 0.74448 (17) | 0.45644 (15) | 0.48910 (14) | 0.0201 (3) | |
H13 | 0.6581 | 0.5435 | 0.4503 | 0.024* | |
C6 | 0.18851 (18) | 1.20637 (16) | 1.00108 (14) | 0.0236 (3) | |
H6 | 0.1009 | 1.2652 | 1.0748 | 0.028* | |
C17 | 0.87029 (18) | 0.30509 (15) | 0.69590 (14) | 0.0225 (3) | |
H17 | 0.8701 | 0.2881 | 0.7993 | 0.027* | |
C7 | 0.28933 (18) | 1.28633 (15) | 0.90890 (14) | 0.0225 (3) | |
H7 | 0.2714 | 1.3993 | 0.9214 | 0.027* | |
C2 | 0.54324 (18) | 0.80948 (14) | 0.61596 (13) | 0.0194 (3) | |
H2A | 0.6499 | 0.7553 | 0.5486 | 0.023* | |
H2B | 0.4369 | 0.8322 | 0.5587 | 0.023* | |
C16 | 0.99632 (18) | 0.19957 (16) | 0.59981 (16) | 0.0262 (3) | |
H16 | 1.0826 | 0.1117 | 0.6377 | 0.031* | |
C15 | 0.99711 (18) | 0.22168 (16) | 0.44774 (16) | 0.0257 (3) | |
H15 | 1.0836 | 0.1492 | 0.3819 | 0.031* | |
C14 | 0.87098 (18) | 0.35004 (16) | 0.39325 (15) | 0.0234 (3) | |
H14 | 0.8711 | 0.3653 | 0.2896 | 0.028* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0259 (5) | 0.0181 (4) | 0.0172 (4) | −0.0084 (4) | 0.0039 (3) | 0.0016 (3) |
O4 | 0.0288 (5) | 0.0228 (5) | 0.0160 (4) | −0.0104 (4) | 0.0013 (4) | 0.0049 (3) |
C9 | 0.0191 (6) | 0.0210 (6) | 0.0126 (5) | −0.0055 (5) | −0.0035 (4) | 0.0035 (4) |
C4 | 0.0207 (6) | 0.0212 (6) | 0.0126 (6) | −0.0080 (5) | −0.0045 (4) | 0.0047 (4) |
C12 | 0.0199 (6) | 0.0184 (6) | 0.0185 (6) | −0.0085 (5) | −0.0026 (5) | 0.0024 (5) |
C3 | 0.0213 (6) | 0.0201 (6) | 0.0125 (6) | −0.0094 (5) | −0.0017 (4) | 0.0024 (4) |
C10 | 0.0201 (6) | 0.0200 (6) | 0.0142 (6) | −0.0063 (5) | −0.0046 (5) | 0.0031 (5) |
C8 | 0.0261 (7) | 0.0211 (6) | 0.0177 (6) | −0.0098 (5) | −0.0057 (5) | 0.0057 (5) |
C11 | 0.0232 (6) | 0.0210 (6) | 0.0128 (6) | −0.0098 (5) | −0.0040 (5) | 0.0039 (5) |
C5 | 0.0209 (6) | 0.0250 (6) | 0.0166 (6) | −0.0071 (5) | −0.0017 (5) | 0.0035 (5) |
C13 | 0.0219 (6) | 0.0208 (6) | 0.0185 (6) | −0.0064 (5) | −0.0041 (5) | 0.0022 (5) |
C6 | 0.0233 (7) | 0.0256 (7) | 0.0197 (6) | −0.0029 (5) | −0.0014 (5) | −0.0013 (5) |
C17 | 0.0248 (7) | 0.0236 (6) | 0.0206 (6) | −0.0086 (5) | −0.0043 (5) | 0.0055 (5) |
C7 | 0.0282 (7) | 0.0181 (6) | 0.0215 (6) | −0.0053 (5) | −0.0077 (5) | 0.0019 (5) |
C2 | 0.0267 (7) | 0.0184 (6) | 0.0138 (6) | −0.0076 (5) | 0.0000 (5) | 0.0022 (5) |
C16 | 0.0227 (7) | 0.0230 (7) | 0.0312 (7) | −0.0026 (5) | −0.0050 (5) | 0.0040 (5) |
C15 | 0.0204 (7) | 0.0268 (7) | 0.0290 (7) | −0.0066 (5) | 0.0029 (5) | −0.0045 (5) |
C14 | 0.0256 (7) | 0.0279 (7) | 0.0183 (6) | −0.0105 (5) | 0.0001 (5) | −0.0013 (5) |
O1—C9 | 1.3664 (14) | C5—C6 | 1.3808 (18) |
O1—C2 | 1.4462 (14) | C5—H5 | 0.9500 |
O4—C4 | 1.2288 (15) | C13—C14 | 1.3882 (18) |
C9—C8 | 1.3912 (17) | C13—H13 | 0.9500 |
C9—C10 | 1.4035 (17) | C6—C7 | 1.4000 (19) |
C4—C10 | 1.4770 (17) | C6—H6 | 0.9500 |
C4—C3 | 1.4915 (17) | C17—C16 | 1.3842 (18) |
C12—C13 | 1.4040 (17) | C17—H17 | 0.9500 |
C12—C17 | 1.4045 (17) | C7—H7 | 0.9500 |
C12—C11 | 1.4659 (17) | C2—H2A | 0.9900 |
C3—C11 | 1.3428 (17) | C2—H2B | 0.9900 |
C3—C2 | 1.5046 (16) | C16—C15 | 1.394 (2) |
C10—C5 | 1.4022 (17) | C16—H16 | 0.9500 |
C8—C7 | 1.3834 (18) | C15—C14 | 1.3852 (19) |
C8—H8 | 0.9500 | C15—H15 | 0.9500 |
C11—H11 | 0.9500 | C14—H14 | 0.9500 |
C9—O1—C2 | 115.34 (9) | C14—C13—H13 | 119.6 |
O1—C9—C8 | 116.88 (11) | C12—C13—H13 | 119.6 |
O1—C9—C10 | 122.40 (11) | C5—C6—C7 | 119.76 (12) |
C8—C9—C10 | 120.69 (12) | C5—C6—H6 | 120.1 |
O4—C4—C10 | 122.27 (11) | C7—C6—H6 | 120.1 |
O4—C4—C3 | 122.37 (11) | C16—C17—C12 | 120.92 (12) |
C10—C4—C3 | 115.35 (10) | C16—C17—H17 | 119.5 |
C13—C12—C17 | 118.03 (11) | C12—C17—H17 | 119.5 |
C13—C12—C11 | 123.52 (11) | C8—C7—C6 | 120.34 (12) |
C17—C12—C11 | 118.37 (11) | C8—C7—H7 | 119.8 |
C11—C3—C4 | 118.95 (11) | C6—C7—H7 | 119.8 |
C11—C3—C2 | 126.81 (11) | O1—C2—C3 | 111.90 (10) |
C4—C3—C2 | 114.23 (10) | O1—C2—H2A | 109.2 |
C5—C10—C9 | 118.55 (11) | C3—C2—H2A | 109.2 |
C5—C10—C4 | 121.13 (11) | O1—C2—H2B | 109.2 |
C9—C10—C4 | 120.13 (11) | C3—C2—H2B | 109.2 |
C7—C8—C9 | 119.77 (11) | H2A—C2—H2B | 107.9 |
C7—C8—H8 | 120.1 | C17—C16—C15 | 120.25 (12) |
C9—C8—H8 | 120.1 | C17—C16—H16 | 119.9 |
C3—C11—C12 | 129.45 (11) | C15—C16—H16 | 119.9 |
C3—C11—H11 | 115.3 | C14—C15—C16 | 119.59 (12) |
C12—C11—H11 | 115.3 | C14—C15—H15 | 120.2 |
C6—C5—C10 | 120.84 (12) | C16—C15—H15 | 120.2 |
C6—C5—H5 | 119.6 | C15—C14—C13 | 120.42 (12) |
C10—C5—H5 | 119.6 | C15—C14—H14 | 119.8 |
C14—C13—C12 | 120.78 (12) | C13—C14—H14 | 119.8 |
C2—O1—C9—C8 | −158.11 (11) | C13—C12—C11—C3 | −29.7 (2) |
C2—O1—C9—C10 | 24.05 (16) | C17—C12—C11—C3 | 153.47 (13) |
O4—C4—C3—C11 | −21.46 (17) | C9—C10—C5—C6 | 0.20 (18) |
C10—C4—C3—C11 | 157.66 (11) | C4—C10—C5—C6 | 175.21 (11) |
O4—C4—C3—C2 | 159.17 (12) | C17—C12—C13—C14 | −1.21 (18) |
C10—C4—C3—C2 | −21.72 (14) | C11—C12—C13—C14 | −178.02 (11) |
O1—C9—C10—C5 | 179.55 (10) | C10—C5—C6—C7 | −1.62 (19) |
C8—C9—C10—C5 | 1.79 (18) | C13—C12—C17—C16 | 1.34 (18) |
O1—C9—C10—C4 | 4.49 (18) | C11—C12—C17—C16 | 178.32 (11) |
C8—C9—C10—C4 | −173.27 (11) | C9—C8—C7—C6 | 0.90 (19) |
O4—C4—C10—C5 | −0.65 (18) | C5—C6—C7—C8 | 1.08 (19) |
C3—C4—C10—C5 | −179.76 (10) | C9—O1—C2—C3 | −50.13 (14) |
O4—C4—C10—C9 | 174.29 (11) | C11—C3—C2—O1 | −130.51 (13) |
C3—C4—C10—C9 | −4.83 (16) | C4—C3—C2—O1 | 48.81 (14) |
O1—C9—C8—C7 | 179.78 (11) | C12—C17—C16—C15 | −0.8 (2) |
C10—C9—C8—C7 | −2.35 (18) | C17—C16—C15—C14 | 0.0 (2) |
C4—C3—C11—C12 | 177.04 (11) | C16—C15—C14—C13 | 0.1 (2) |
C2—C3—C11—C12 | −3.7 (2) | C12—C13—C14—C15 | 0.52 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O4i | 0.95 | 2.56 | 3.4153 (15) | 150 |
C17—H17···O4i | 0.95 | 2.56 | 3.4050 (16) | 148 |
C7—H7···O4ii | 0.95 | 2.69 | 3.6131 (16) | 166 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, y+1, z. |
C17H14O3 | Z = 4 |
Mr = 266.28 | F(000) = 560 |
Triclinic, P1 | Dx = 1.368 Mg m−3 |
a = 7.5570 (3) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 12.3558 (4) Å | Cell parameters from 8925 reflections |
c = 14.4044 (6) Å | θ = 3.7–71.9° |
α = 82.748 (3)° | µ = 0.76 mm−1 |
β = 87.126 (3)° | T = 100 K |
γ = 75.768 (3)° | Needle, colorless |
V = 1293.02 (9) Å3 | 0.3 × 0.08 × 0.06 mm |
XtaLAB Synergy Dualflex HyPix diffractometer | 5118 independent reflections |
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source | 4669 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.020 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 66.6°, θmin = 3.1° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2019) | k = −14→14 |
Tmin = 0.671, Tmax = 1.000 | l = −17→17 |
5118 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.070 | H-atom parameters constrained |
wR(F2) = 0.200 | w = 1/[σ2(Fo2) + (0.1415P)2 + 0.4525P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
5118 reflections | Δρmax = 0.63 e Å−3 |
364 parameters | Δρmin = −0.33 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. |
Refinement. Refined as a 2-component twin. |
x | y | z | Uiso*/Ueq | ||
O22 | 0.4818 (3) | 0.40499 (15) | 0.86434 (13) | 0.0291 (4) | |
O21 | −0.0050 (2) | −0.08126 (14) | 0.93266 (12) | 0.0242 (4) | |
O24 | 0.4539 (3) | −0.26141 (17) | 0.81175 (16) | 0.0385 (5) | |
C32 | 0.4383 (3) | 0.0781 (2) | 0.85181 (17) | 0.0219 (5) | |
C34 | 0.3282 (3) | 0.2796 (2) | 0.81810 (17) | 0.0229 (5) | |
H34 | 0.2396 | 0.3429 | 0.7911 | 0.028* | |
C27 | −0.1267 (4) | −0.3485 (2) | 0.94295 (18) | 0.0282 (6) | |
H27 | −0.2211 | −0.3822 | 0.9690 | 0.034* | |
C29 | 0.0045 (3) | −0.1894 (2) | 0.91708 (16) | 0.0217 (5) | |
C37 | 0.5883 (3) | 0.0959 (2) | 0.89517 (17) | 0.0245 (5) | |
H37 | 0.6791 | 0.0328 | 0.9205 | 0.029* | |
C31 | 0.4290 (3) | −0.0379 (2) | 0.84604 (17) | 0.0241 (5) | |
H31 | 0.5435 | −0.0899 | 0.8398 | 0.029* | |
C30 | 0.1541 (3) | −0.2517 (2) | 0.86905 (17) | 0.0223 (5) | |
C33 | 0.3082 (3) | 0.1718 (2) | 0.81231 (17) | 0.0232 (5) | |
H33 | 0.2062 | 0.1616 | 0.7815 | 0.028* | |
C28 | −0.1342 (4) | −0.2376 (2) | 0.95432 (17) | 0.0260 (5) | |
H28 | −0.2338 | −0.1951 | 0.9874 | 0.031* | |
C24 | 0.3103 (4) | −0.2035 (2) | 0.83950 (18) | 0.0253 (6) | |
C36 | 0.6085 (3) | 0.2030 (2) | 0.90225 (17) | 0.0251 (5) | |
H36 | 0.7102 | 0.2134 | 0.9332 | 0.030* | |
C23 | 0.2839 (3) | −0.0813 (2) | 0.84823 (17) | 0.0229 (5) | |
C22 | 0.0881 (3) | −0.0182 (2) | 0.86382 (18) | 0.0242 (5) | |
H22A | 0.0863 | 0.0552 | 0.8852 | 0.029* | |
H22B | 0.0228 | −0.0034 | 0.8039 | 0.029* | |
C35 | 0.4763 (3) | 0.2955 (2) | 0.86302 (17) | 0.0233 (5) | |
C25 | 0.1572 (4) | −0.3633 (2) | 0.85732 (17) | 0.0249 (5) | |
H25 | 0.2560 | −0.4061 | 0.8240 | 0.030* | |
C26 | 0.0184 (4) | −0.4111 (2) | 0.89352 (18) | 0.0276 (6) | |
H26 | 0.0213 | −0.4866 | 0.8849 | 0.033* | |
C38 | 0.6384 (4) | 0.4274 (2) | 0.9020 (2) | 0.0372 (7) | |
H38A | 0.6447 | 0.4006 | 0.9691 | 0.056* | |
H38B | 0.6293 | 0.5085 | 0.8929 | 0.056* | |
H38C | 0.7487 | 0.3884 | 0.8700 | 0.056* | |
O1 | 0.5023 (2) | 0.60541 (14) | 0.43853 (12) | 0.0229 (4) | |
O4 | 0.0517 (2) | 0.82132 (15) | 0.32039 (14) | 0.0303 (5) | |
O2 | 0.0227 (3) | 0.14104 (15) | 0.35386 (13) | 0.0298 (4) | |
C12 | 0.0649 (3) | 0.4712 (2) | 0.35122 (17) | 0.0226 (5) | |
C14 | 0.1829 (3) | 0.2797 (2) | 0.31505 (17) | 0.0239 (5) | |
H14 | 0.2757 | 0.2250 | 0.2883 | 0.029* | |
C3 | 0.2212 (3) | 0.6308 (2) | 0.35305 (16) | 0.0217 (5) | |
C4 | 0.1961 (3) | 0.7548 (2) | 0.34556 (17) | 0.0230 (5) | |
C11 | 0.0749 (3) | 0.5888 (2) | 0.34865 (17) | 0.0225 (5) | |
H11 | −0.0389 | 0.6428 | 0.3431 | 0.027* | |
C8 | 0.6381 (3) | 0.7532 (2) | 0.45601 (17) | 0.0252 (5) | |
H8 | 0.7344 | 0.7008 | 0.4892 | 0.030* | |
C7 | 0.6363 (4) | 0.8663 (2) | 0.44207 (18) | 0.0276 (6) | |
H7 | 0.7320 | 0.8916 | 0.4661 | 0.033* | |
C2 | 0.4134 (3) | 0.5615 (2) | 0.37033 (17) | 0.0214 (5) | |
H2A | 0.4103 | 0.4829 | 0.3930 | 0.026* | |
H2B | 0.4846 | 0.5612 | 0.3107 | 0.026* | |
C15 | 0.0292 (3) | 0.2501 (2) | 0.35630 (17) | 0.0241 (5) | |
C13 | 0.2016 (3) | 0.3887 (2) | 0.31268 (17) | 0.0224 (5) | |
H13 | 0.3080 | 0.4080 | 0.2847 | 0.027* | |
C10 | 0.3523 (3) | 0.7936 (2) | 0.37333 (16) | 0.0219 (5) | |
C5 | 0.3548 (3) | 0.9078 (2) | 0.35931 (17) | 0.0235 (5) | |
H5 | 0.2587 | 0.9606 | 0.3263 | 0.028* | |
C9 | 0.4980 (3) | 0.7173 (2) | 0.42096 (16) | 0.0215 (5) | |
C17 | −0.0894 (3) | 0.4396 (2) | 0.39111 (17) | 0.0235 (5) | |
H17 | −0.1845 | 0.4945 | 0.4161 | 0.028* | |
C16 | −0.1079 (3) | 0.3297 (2) | 0.39524 (18) | 0.0259 (5) | |
H16 | −0.2127 | 0.3093 | 0.4242 | 0.031* | |
C6 | 0.4947 (4) | 0.9441 (2) | 0.39283 (18) | 0.0277 (6) | |
H6 | 0.4954 | 1.0215 | 0.3827 | 0.033* | |
C18 | −0.1317 (4) | 0.1054 (2) | 0.3944 (2) | 0.0360 (7) | |
H18A | −0.2428 | 0.1530 | 0.3650 | 0.054* | |
H18B | −0.1379 | 0.1117 | 0.4617 | 0.054* | |
H18C | −0.1208 | 0.0270 | 0.3844 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O22 | 0.0341 (10) | 0.0234 (9) | 0.0310 (10) | −0.0096 (8) | −0.0063 (8) | −0.0002 (7) |
O21 | 0.0247 (9) | 0.0204 (9) | 0.0266 (9) | −0.0054 (7) | 0.0066 (7) | −0.0024 (7) |
O24 | 0.0279 (10) | 0.0297 (10) | 0.0585 (14) | −0.0065 (8) | 0.0143 (9) | −0.0143 (9) |
C32 | 0.0189 (11) | 0.0262 (13) | 0.0194 (11) | −0.0050 (9) | 0.0049 (9) | −0.0010 (9) |
C34 | 0.0221 (12) | 0.0237 (12) | 0.0207 (12) | −0.0038 (9) | 0.0008 (9) | 0.0022 (9) |
C27 | 0.0312 (14) | 0.0313 (14) | 0.0245 (13) | −0.0133 (11) | −0.0008 (10) | −0.0003 (11) |
C29 | 0.0227 (12) | 0.0211 (12) | 0.0195 (11) | −0.0024 (9) | −0.0027 (9) | −0.0008 (9) |
C37 | 0.0188 (12) | 0.0294 (13) | 0.0233 (12) | −0.0048 (9) | 0.0023 (9) | 0.0015 (10) |
C31 | 0.0219 (12) | 0.0249 (13) | 0.0232 (12) | −0.0031 (9) | 0.0015 (10) | −0.0004 (10) |
C30 | 0.0217 (12) | 0.0240 (12) | 0.0198 (12) | −0.0037 (9) | −0.0019 (9) | −0.0003 (9) |
C33 | 0.0224 (12) | 0.0285 (13) | 0.0194 (11) | −0.0086 (10) | 0.0015 (9) | −0.0008 (10) |
C28 | 0.0270 (13) | 0.0281 (13) | 0.0224 (12) | −0.0068 (10) | 0.0011 (10) | −0.0018 (10) |
C24 | 0.0256 (13) | 0.0233 (13) | 0.0260 (13) | −0.0038 (10) | 0.0027 (10) | −0.0040 (10) |
C36 | 0.0221 (12) | 0.0308 (14) | 0.0224 (12) | −0.0076 (10) | −0.0022 (10) | 0.0003 (10) |
C23 | 0.0240 (12) | 0.0246 (13) | 0.0191 (11) | −0.0046 (10) | 0.0021 (9) | −0.0026 (9) |
C22 | 0.0224 (12) | 0.0213 (12) | 0.0280 (13) | −0.0064 (9) | 0.0057 (10) | 0.0001 (10) |
C35 | 0.0257 (13) | 0.0251 (13) | 0.0193 (12) | −0.0082 (10) | 0.0033 (9) | −0.0016 (9) |
C25 | 0.0298 (13) | 0.0220 (12) | 0.0213 (12) | −0.0024 (10) | −0.0038 (10) | −0.0028 (10) |
C26 | 0.0358 (14) | 0.0217 (12) | 0.0262 (13) | −0.0087 (10) | −0.0052 (11) | −0.0003 (10) |
C38 | 0.0448 (17) | 0.0300 (14) | 0.0411 (16) | −0.0170 (12) | −0.0111 (13) | −0.0009 (12) |
O1 | 0.0236 (8) | 0.0196 (8) | 0.0249 (9) | −0.0051 (7) | −0.0048 (7) | 0.0009 (7) |
O4 | 0.0236 (9) | 0.0231 (9) | 0.0421 (11) | −0.0036 (7) | −0.0078 (8) | 0.0030 (8) |
O2 | 0.0324 (10) | 0.0237 (9) | 0.0347 (10) | −0.0108 (8) | 0.0047 (8) | −0.0035 (8) |
C12 | 0.0218 (12) | 0.0240 (13) | 0.0217 (12) | −0.0047 (10) | −0.0051 (9) | −0.0018 (10) |
C14 | 0.0211 (12) | 0.0277 (13) | 0.0213 (12) | −0.0025 (9) | −0.0006 (9) | −0.0037 (10) |
C3 | 0.0259 (13) | 0.0214 (12) | 0.0168 (11) | −0.0045 (10) | −0.0002 (9) | −0.0012 (9) |
C4 | 0.0252 (13) | 0.0213 (13) | 0.0209 (12) | −0.0042 (10) | 0.0006 (10) | 0.0009 (9) |
C11 | 0.0230 (12) | 0.0233 (13) | 0.0205 (12) | −0.0045 (10) | −0.0023 (9) | −0.0018 (9) |
C8 | 0.0247 (12) | 0.0275 (13) | 0.0221 (12) | −0.0045 (10) | −0.0021 (10) | −0.0012 (10) |
C7 | 0.0307 (13) | 0.0303 (14) | 0.0252 (13) | −0.0131 (11) | 0.0000 (10) | −0.0048 (10) |
C2 | 0.0216 (12) | 0.0209 (12) | 0.0226 (12) | −0.0067 (9) | −0.0016 (9) | −0.0025 (9) |
C15 | 0.0265 (13) | 0.0240 (13) | 0.0218 (12) | −0.0069 (10) | −0.0024 (10) | −0.0001 (10) |
C13 | 0.0193 (11) | 0.0275 (13) | 0.0208 (12) | −0.0069 (10) | −0.0008 (9) | −0.0014 (10) |
C10 | 0.0216 (12) | 0.0237 (12) | 0.0192 (12) | −0.0045 (9) | 0.0025 (9) | −0.0007 (9) |
C5 | 0.0253 (13) | 0.0234 (13) | 0.0203 (12) | −0.0045 (10) | 0.0037 (9) | −0.0011 (10) |
C9 | 0.0238 (12) | 0.0219 (12) | 0.0179 (11) | −0.0049 (10) | 0.0030 (9) | −0.0018 (9) |
C17 | 0.0207 (12) | 0.0257 (13) | 0.0237 (12) | −0.0042 (9) | 0.0003 (9) | −0.0043 (10) |
C16 | 0.0227 (12) | 0.0295 (13) | 0.0262 (13) | −0.0084 (10) | 0.0013 (10) | −0.0019 (10) |
C6 | 0.0340 (14) | 0.0241 (13) | 0.0268 (13) | −0.0100 (10) | 0.0030 (10) | −0.0050 (10) |
C18 | 0.0433 (16) | 0.0287 (14) | 0.0398 (16) | −0.0180 (12) | 0.0112 (13) | −0.0049 (12) |
O22—C35 | 1.366 (3) | O1—C9 | 1.366 (3) |
O22—C38 | 1.427 (3) | O1—C2 | 1.446 (3) |
O21—C29 | 1.366 (3) | O4—C4 | 1.233 (3) |
O21—C22 | 1.446 (3) | O2—C15 | 1.365 (3) |
O24—C24 | 1.223 (3) | O2—C18 | 1.419 (3) |
C32—C37 | 1.397 (4) | C12—C17 | 1.394 (4) |
C32—C33 | 1.400 (4) | C12—C13 | 1.408 (3) |
C32—C31 | 1.465 (3) | C12—C11 | 1.469 (3) |
C34—C35 | 1.387 (4) | C14—C13 | 1.384 (4) |
C34—C33 | 1.391 (3) | C14—C15 | 1.386 (4) |
C34—H34 | 0.9500 | C14—H14 | 0.9500 |
C27—C28 | 1.388 (4) | C3—C11 | 1.339 (4) |
C27—C26 | 1.397 (4) | C3—C4 | 1.488 (3) |
C27—H27 | 0.9500 | C3—C2 | 1.509 (3) |
C29—C28 | 1.382 (4) | C4—C10 | 1.469 (4) |
C29—C30 | 1.407 (3) | C11—H11 | 0.9500 |
C37—C36 | 1.385 (4) | C8—C9 | 1.383 (4) |
C37—H37 | 0.9500 | C8—C7 | 1.384 (4) |
C31—C23 | 1.331 (4) | C8—H8 | 0.9500 |
C31—H31 | 0.9500 | C7—C6 | 1.404 (4) |
C30—C25 | 1.404 (3) | C7—H7 | 0.9500 |
C30—C24 | 1.470 (4) | C2—H2A | 0.9900 |
C33—H33 | 0.9500 | C2—H2B | 0.9900 |
C28—H28 | 0.9500 | C15—C16 | 1.391 (4) |
C24—C23 | 1.494 (3) | C13—H13 | 0.9500 |
C36—C35 | 1.398 (4) | C10—C5 | 1.404 (3) |
C36—H36 | 0.9500 | C10—C9 | 1.405 (3) |
C23—C22 | 1.514 (3) | C5—C6 | 1.375 (4) |
C22—H22A | 0.9900 | C5—H5 | 0.9500 |
C22—H22B | 0.9900 | C17—C16 | 1.393 (4) |
C25—C26 | 1.376 (4) | C17—H17 | 0.9500 |
C25—H25 | 0.9500 | C16—H16 | 0.9500 |
C26—H26 | 0.9500 | C6—H6 | 0.9500 |
C38—H38A | 0.9800 | C18—H18A | 0.9800 |
C38—H38B | 0.9800 | C18—H18B | 0.9800 |
C38—H38C | 0.9800 | C18—H18C | 0.9800 |
C35—O22—C38 | 118.4 (2) | C9—O1—C2 | 115.39 (18) |
C29—O21—C22 | 115.55 (18) | C15—O2—C18 | 118.5 (2) |
C37—C32—C33 | 118.5 (2) | C17—C12—C13 | 117.9 (2) |
C37—C32—C31 | 118.4 (2) | C17—C12—C11 | 118.9 (2) |
C33—C32—C31 | 123.1 (2) | C13—C12—C11 | 123.3 (2) |
C35—C34—C33 | 120.5 (2) | C13—C14—C15 | 120.2 (2) |
C35—C34—H34 | 119.8 | C13—C14—H14 | 119.9 |
C33—C34—H34 | 119.8 | C15—C14—H14 | 119.9 |
C28—C27—C26 | 120.6 (2) | C11—C3—C4 | 119.2 (2) |
C28—C27—H27 | 119.7 | C11—C3—C2 | 125.0 (2) |
C26—C27—H27 | 119.7 | C4—C3—C2 | 115.8 (2) |
O21—C29—C28 | 117.6 (2) | O4—C4—C10 | 121.8 (2) |
O21—C29—C30 | 121.5 (2) | O4—C4—C3 | 122.4 (2) |
C28—C29—C30 | 120.9 (2) | C10—C4—C3 | 115.8 (2) |
C36—C37—C32 | 121.9 (2) | C3—C11—C12 | 129.4 (2) |
C36—C37—H37 | 119.0 | C3—C11—H11 | 115.3 |
C32—C37—H37 | 119.0 | C12—C11—H11 | 115.3 |
C23—C31—C32 | 129.6 (2) | C9—C8—C7 | 119.2 (2) |
C23—C31—H31 | 115.2 | C9—C8—H8 | 120.4 |
C32—C31—H31 | 115.2 | C7—C8—H8 | 120.4 |
C25—C30—C29 | 118.5 (2) | C8—C7—C6 | 120.7 (2) |
C25—C30—C24 | 121.2 (2) | C8—C7—H7 | 119.7 |
C29—C30—C24 | 120.1 (2) | C6—C7—H7 | 119.7 |
C34—C33—C32 | 120.1 (2) | O1—C2—C3 | 111.52 (19) |
C34—C33—H33 | 120.0 | O1—C2—H2A | 109.3 |
C32—C33—H33 | 120.0 | C3—C2—H2A | 109.3 |
C29—C28—C27 | 119.5 (2) | O1—C2—H2B | 109.3 |
C29—C28—H28 | 120.3 | C3—C2—H2B | 109.3 |
C27—C28—H28 | 120.3 | H2A—C2—H2B | 108.0 |
O24—C24—C30 | 121.4 (2) | O2—C15—C14 | 115.7 (2) |
O24—C24—C23 | 122.7 (2) | O2—C15—C16 | 124.0 (2) |
C30—C24—C23 | 115.9 (2) | C14—C15—C16 | 120.3 (2) |
C37—C36—C35 | 118.7 (2) | C14—C13—C12 | 120.8 (2) |
C37—C36—H36 | 120.6 | C14—C13—H13 | 119.6 |
C35—C36—H36 | 120.6 | C12—C13—H13 | 119.6 |
C31—C23—C24 | 119.4 (2) | C5—C10—C9 | 118.3 (2) |
C31—C23—C22 | 125.5 (2) | C5—C10—C4 | 121.4 (2) |
C24—C23—C22 | 115.0 (2) | C9—C10—C4 | 120.1 (2) |
O21—C22—C23 | 111.40 (19) | C6—C5—C10 | 120.8 (2) |
O21—C22—H22A | 109.3 | C6—C5—H5 | 119.6 |
C23—C22—H22A | 109.3 | C10—C5—H5 | 119.6 |
O21—C22—H22B | 109.3 | O1—C9—C8 | 117.3 (2) |
C23—C22—H22B | 109.3 | O1—C9—C10 | 121.3 (2) |
H22A—C22—H22B | 108.0 | C8—C9—C10 | 121.4 (2) |
O22—C35—C34 | 115.4 (2) | C16—C17—C12 | 121.7 (2) |
O22—C35—C36 | 124.3 (2) | C16—C17—H17 | 119.1 |
C34—C35—C36 | 120.3 (2) | C12—C17—H17 | 119.1 |
C26—C25—C30 | 120.7 (2) | C15—C16—C17 | 119.1 (2) |
C26—C25—H25 | 119.6 | C15—C16—H16 | 120.5 |
C30—C25—H25 | 119.6 | C17—C16—H16 | 120.5 |
C25—C26—C27 | 119.8 (2) | C5—C6—C7 | 119.7 (2) |
C25—C26—H26 | 120.1 | C5—C6—H6 | 120.2 |
C27—C26—H26 | 120.1 | C7—C6—H6 | 120.2 |
O22—C38—H38A | 109.5 | O2—C18—H18A | 109.5 |
O22—C38—H38B | 109.5 | O2—C18—H18B | 109.5 |
H38A—C38—H38B | 109.5 | H18A—C18—H18B | 109.5 |
O22—C38—H38C | 109.5 | O2—C18—H18C | 109.5 |
H38A—C38—H38C | 109.5 | H18A—C18—H18C | 109.5 |
H38B—C38—H38C | 109.5 | H18B—C18—H18C | 109.5 |
C22—O21—C29—C28 | −154.3 (2) | C11—C3—C4—O4 | −12.1 (4) |
C22—O21—C29—C30 | 28.9 (3) | C2—C3—C4—O4 | 171.0 (2) |
C33—C32—C37—C36 | 1.8 (4) | C11—C3—C4—C10 | 165.8 (2) |
C31—C32—C37—C36 | 179.1 (2) | C2—C3—C4—C10 | −11.1 (3) |
C37—C32—C31—C23 | 147.3 (3) | C4—C3—C11—C12 | 177.8 (2) |
C33—C32—C31—C23 | −35.7 (4) | C2—C3—C11—C12 | −5.6 (4) |
O21—C29—C30—C25 | 178.6 (2) | C17—C12—C11—C3 | 148.4 (3) |
C28—C29—C30—C25 | 1.8 (3) | C13—C12—C11—C3 | −33.6 (4) |
O21—C29—C30—C24 | 3.8 (3) | C9—C8—C7—C6 | −0.2 (4) |
C28—C29—C30—C24 | −172.9 (2) | C9—O1—C2—C3 | −52.0 (3) |
C35—C34—C33—C32 | −0.1 (4) | C11—C3—C2—O1 | −134.7 (2) |
C37—C32—C33—C34 | −1.1 (4) | C4—C3—C2—O1 | 42.0 (3) |
C31—C32—C33—C34 | −178.2 (2) | C18—O2—C15—C14 | −179.6 (2) |
O21—C29—C28—C27 | −177.8 (2) | C18—O2—C15—C16 | −0.9 (4) |
C30—C29—C28—C27 | −0.9 (4) | C13—C14—C15—O2 | 179.1 (2) |
C26—C27—C28—C29 | −0.7 (4) | C13—C14—C15—C16 | 0.3 (4) |
C25—C30—C24—O24 | −6.8 (4) | C15—C14—C13—C12 | −0.5 (4) |
C29—C30—C24—O24 | 167.8 (2) | C17—C12—C13—C14 | −0.4 (3) |
C25—C30—C24—C23 | 174.9 (2) | C11—C12—C13—C14 | −178.4 (2) |
C29—C30—C24—C23 | −10.5 (3) | O4—C4—C10—C5 | −9.7 (4) |
C32—C37—C36—C35 | −1.3 (4) | C3—C4—C10—C5 | 172.4 (2) |
C32—C31—C23—C24 | 179.0 (2) | O4—C4—C10—C9 | 165.8 (2) |
C32—C31—C23—C22 | −4.1 (4) | C3—C4—C10—C9 | −12.1 (3) |
O24—C24—C23—C31 | −15.2 (4) | C9—C10—C5—C6 | −1.1 (3) |
C30—C24—C23—C31 | 163.1 (2) | C4—C10—C5—C6 | 174.4 (2) |
O24—C24—C23—C22 | 167.7 (2) | C2—O1—C9—C8 | −152.8 (2) |
C30—C24—C23—C22 | −14.0 (3) | C2—O1—C9—C10 | 30.3 (3) |
C29—O21—C22—C23 | −52.1 (3) | C7—C8—C9—O1 | −178.2 (2) |
C31—C23—C22—O21 | −132.7 (3) | C7—C8—C9—C10 | −1.3 (4) |
C24—C23—C22—O21 | 44.2 (3) | C5—C10—C9—O1 | 178.7 (2) |
C38—O22—C35—C34 | −174.6 (2) | C4—C10—C9—O1 | 3.2 (3) |
C38—O22—C35—C36 | 4.7 (4) | C5—C10—C9—C8 | 2.0 (3) |
C33—C34—C35—O22 | 180.0 (2) | C4—C10—C9—C8 | −173.6 (2) |
C33—C34—C35—C36 | 0.6 (4) | C13—C12—C17—C16 | 1.5 (4) |
C37—C36—C35—O22 | −179.2 (2) | C11—C12—C17—C16 | 179.6 (2) |
C37—C36—C35—C34 | 0.1 (4) | O2—C15—C16—C17 | −177.9 (2) |
C29—C30—C25—C26 | −1.2 (4) | C14—C15—C16—C17 | 0.8 (4) |
C24—C30—C25—C26 | 173.5 (2) | C12—C17—C16—C15 | −1.7 (4) |
C30—C25—C26—C27 | −0.3 (4) | C10—C5—C6—C7 | −0.3 (4) |
C28—C27—C26—C25 | 1.3 (4) | C8—C7—C6—C5 | 1.0 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···O22i | 0.99 | 2.51 | 3.430 (3) | 154 |
C2—H2A···O1i | 0.99 | 2.58 | 3.215 (3) | 122 |
C5—H5···O2ii | 0.95 | 2.55 | 3.319 (3) | 138 |
C14—H14···O24iii | 0.95 | 2.54 | 3.196 (3) | 127 |
C17—H17···O1iv | 0.95 | 2.45 | 3.349 (3) | 157 |
C25—H25···O22v | 0.95 | 2.55 | 3.275 (3) | 133 |
C33—H33···O4vi | 0.95 | 2.45 | 3.381 (3) | 166 |
C37—H37···O21vii | 0.95 | 2.46 | 3.330 (3) | 153 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z; (iii) −x+1, −y, −z+1; (iv) x−1, y, z; (v) x, y−1, z; (vi) −x, −y+1, −z+1; (vii) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
Compound I | ||||
C11—H11···O4i | 0.95 | 2.47 | 3.353 (3) | 154 |
C17—H17···O4i | 0.95 | 2.64 | 3.353 (2) | 132 |
C21—H21···O4ii | 0.95 | 2.68 | 3.267 (3) | 120 |
C6—H6···Cg4iii | 0.95 | 2.83 | 3.736 (2) | 160 |
C15—H15···Cg4iv | 0.95 | 2.89 | 3.730 (2) | 148 |
C16—H16···Cg2iv | 0.95 | 2.84 | 3.539 (2) | 131 |
Compound II | ||||
C2—H2···O4v | 1.00 | 2.27 | 3.174 (2) | 149 |
C5—H5···O1vi | 0.95 | 2.54 | 3.408 (2) | 152 |
C24—H24···O4vii | 0.95 | 2.71 | 3.487 (2) | 140 |
Compound III | ||||
C11—H11···O4viii | 0.95 | 2.54 | 3.3635 (14) | 145 |
C17—H17···O4viii | 0.95 | 2.69 | 3.5025 (15) | 144 |
C24—H24···O4ix | 0.95 | 2.60 | 3.2731 (15) | 128 |
C6—H6···Cg4x | 0.95 | 2.52 | 3.4654 (15) | 174 |
Compound IV | ||||
C2—H2···O34xi | 1.00 | 2.45 | 3.3434 (15) | 148 |
C6—H6···O61xii | 0.95 | 2.40 | 3.2676 (16) | 151 |
C14—H14···O1xiii | 0.95 | 2.46 | 3.3750 (15) | 161 |
C32—H32···O64xiv | 1.00 | 2.37 | 3.2348 (15) | 144 |
C36—H36···O1xv | 0.95 | 2.42 | 3.2733 (15) | 150 |
C44—H44···O31xiii | 0.95 | 2.42 | 3.3399 (16) | 162 |
C62—H62···O4xvi | 1.00 | 2.48 | 3.3629 (15) | 146 |
C66—H66···O31xvii | 0.95 | 2.48 | 3.3725 (15) | 157 |
C74—H74···O61xiii | 0.95 | 2.49 | 3.4018 (15) | 161 |
C7—H7···Cg8xviii | 0.95 | 2.97 | 3.7215915) | 136 |
C211—H21B···Cg4xviii | 0.98 | 2.71 | 3.6762 (15) | 169 |
C211—H21C···Cg3xix | 0.98 | 2.91 | 3.6005 (17) | 128 |
C23—H23···Cg9xx | 0.95 | 2.99 | 3.6985 (14) | 133 |
C37—H37···Cg3xxi | 0.95 | 2.98 | 3.7434 (15) | 138 |
C511—H51B···Cg13xvi | 0.98 | 2.75 | 3.6774 (15) | 158 |
C53—H53···Cg4xxii | 0.95 | 2.72 | 3.5324 (15) | 144 |
C811—H81A···Cg9xii | 0.98 | 2.99 | 3.6203 (16) | 123 |
C811—H81B···Cg8xvi | 0.98 | 2.90 | 3.8631 (15) | 167 |
Compound V | ||||
C7—H7···O4xxiii | 0.95 | 2.69 | 3.6131 (16) | 166 |
C11—H11···O4xxiv | 0.95 | 2.56 | 3.4153 (15) | 150 |
C17—H17···O4 xxiv | 0.95 | 2.56 | 3.4050 (16) | 148 |
Compound VI | ||||
C2—H2A···O22 | 0.99 | 2.51 | 3.430 (3) | 154 |
C2—H2B···O1xxv | 0.99 | 2.58 | 3.215 (3) | 122 |
C5—H5···O2xxvi | 0.95 | 2.55 | 3.319 (3) | 138 |
C14—H14···O24xxvii | 0.95 | 2.54 | 3.196 (3) | 127 |
C17—H17···O1xxviii | 0.95 | 2.45 | 3.349 (3) | 157 |
C25—H25···O22xxvi | 0.95 | 2.55 | 3.275 (3) | 133 |
C33—H33···O4xxix | 0.95 | 2.45 | 3.381 (3) | 166 |
C37—H37···O21xxviii | 0.95 | 2.46 | 3.330 (3) | 153 |
C8—H8···Cg3xxix | 0.95 | 2.79 | 3.632 (3) | 149 |
C28—H28···Cg7xxx | 0.95 | 2.74 | 3.573(30 | 147 |
Symmetry codes:
(i) -x, y, -z+1/2;
(ii) -x+1/2, y-1/2, -z+1/2;
(iii) x-1/2, y-1/2, z;
(iv) x+1, y, z;
(v) x, -y+3/2, z-1/2;
(vi) x, -y+3/2, z+1/2;
(vii) x, -y+1/2, z-1/2;
(viii) -x+1, -y, -z+1;
(ix) -x+1, -y, -z;
(x) x-1, y, z;
(xi) -x+1/2, y+1/2, -z+3/2;
(xii) -x+1/2, y+1/2, -z+1/2;
(xiii) x, y+1, z;
(xiv) x+1/2, -y+1/2, z+1/2;
(xv) -x+1/2, y-1/2, -z+3/2;
(xvi) -x+1/2, y-1/2, -z+1/2;
(xvii) x-1/2, -y+1/2, z-1/2,
(xviii) -x-1/2, -y+3/2, z-1/2;
(xix) -x+1/2, y-1/2, -z+3/2;
(xx) x, y, z;
(xxi) x+1/2, -y+3/2, z+1/2;
(xxii) x, y-1, z;
(xxiii) x, y+1, z;
(xxiv) -x+1, -y+1, -z+2;
(xxv) -x+1, -y+3, -z+1;
(xxvi) x, y-1, z;
(xxvii) x, y+1, z;
(xxviii) x+1, y, z;
(xxix) x-1, y, z;
(xxix) -x+1, -y+3, -z+1;
(xxx) -x, -y+2, -z+2. For compound I, Cg2 is the centroid of the C5–C10 ring and Cg4 of the C18–C23 ring; for compound III, Cg4 is the centroid of the C21–C26 ring; for compound IV, Cg3 is the centroid of the C11–C16 ring, Cg4 of the C18–C23 ring, Cg8 of the C41–C46 ring, Cg9 of the C48–C53 ring and Cg13 fo the C71–C76 ring. |
Compound | logP(exp) | milogP(theor) |
I | 4.90 | 5.20 |
II | 4.45 | 5.65 |
III | 3.05 | 5.63 |
IV | 4.79 | 5.26 |
V | 4.23 | 3.62 |
VI | 4.08 | 3.68 |
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