Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618015838/jx3023sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015838/jx30233asup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015838/jx30233bsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015838/jx30233csup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015838/jx30233dsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015838/jx30233esup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015838/jx30233fsup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015838/jx30235asup8.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015838/jx30235bsup9.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618015838/jx30233asup10.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618015838/jx30233bsup11.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618015838/jx30233csup12.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618015838/jx30233dsup13.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618015838/jx30233esup14.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618015838/jx30235asup15.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618015838/jx3023sup16.pdf |
CCDC references: 1877738; 1848662; 1848661; 1848660; 1848659; 1848658; 1848657; 1848656
Data collection: APEX (Bruker, 2010) for (3a), (3b), (3c), (3e), (5b). Cell refinement: SAINT (Bruker, 2010) for (3a), (3b), (3c), (3e), (5b). Data reduction: SAINT (Bruker, 2010) for (3a), (3b), (3c), (3e), (5b). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (3a), (3f); SHELXT (Sheldrick, 2015a) for (3b), (3c), (3d), (3e), (5b); SHELXXS97 (Sheldrick, 2008) for (5a). Program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b) for (3a), (3b), (3c), (3d), (3e), (5a), (5b); XLMP (Sheldrick, 2008) for (3f). For all structures, molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
C23H16O | F(000) = 648 |
Mr = 308.36 | Dx = 1.202 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 5.723 (6) Å | Cell parameters from 2200 reflections |
b = 27.11 (3) Å | θ = 2.4–29.3° |
c = 10.984 (12) Å | µ = 0.07 mm−1 |
β = 89.55 (3)° | T = 200 K |
V = 1704 (3) Å3 | Plate, light brown |
Z = 4 | 0.42 × 0.18 × 0.04 mm |
Bruker SMART APEX CCD area detector diffractometer | 2173 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.203 |
phi and ω scans | θmax = 30.2°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | h = −7→7 |
Tmin = 0.459, Tmax = 0.746 | k = −38→37 |
18018 measured reflections | l = −14→14 |
4776 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.084 | H-atom parameters constrained |
wR(F2) = 0.191 | w = 1/[σ2(Fo2) + (0.055P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
4776 reflections | Δρmax = 0.26 e Å−3 |
217 parameters | Δρmin = −0.20 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 | 0.2923 (3) | 0.40975 (7) | 0.93814 (16) | 0.0546 (5) | |
C1 | 0.3399 (4) | 0.39016 (9) | 0.8400 (2) | 0.0399 (6) | |
C2 | 0.5325 (4) | 0.35511 (9) | 0.8183 (2) | 0.0391 (6) | |
C3 | 0.5241 (4) | 0.33729 (10) | 0.6890 (2) | 0.0465 (6) | |
H3A | 0.4942 | 0.3013 | 0.6865 | 0.056* | |
H3B | 0.6741 | 0.3441 | 0.6467 | 0.056* | |
C4 | 0.3234 (5) | 0.36565 (13) | 0.6278 (3) | 0.0628 (8) | |
H4A | 0.3842 | 0.3864 | 0.5606 | 0.075* | |
H4B | 0.2069 | 0.3424 | 0.5945 | 0.075* | |
C5 | 0.2150 (4) | 0.39702 (9) | 0.7248 (2) | 0.0401 (6) | |
C6 | 0.6908 (4) | 0.34281 (9) | 0.9030 (2) | 0.0456 (6) | |
H6 | 0.6822 | 0.3582 | 0.9805 | 0.055* | |
C7 | 0.8692 (4) | 0.30784 (10) | 0.8810 (2) | 0.0453 (6) | |
C8 | 1.0121 (4) | 0.27709 (10) | 0.8562 (2) | 0.0456 (6) | |
C9 | 1.1707 (4) | 0.23891 (9) | 0.8201 (2) | 0.0420 (6) | |
C10 | 1.3658 (4) | 0.22711 (10) | 0.8903 (3) | 0.0503 (7) | |
H10 | 1.3928 | 0.2441 | 0.9646 | 0.060* | |
C11 | 1.5189 (5) | 0.19091 (11) | 0.8520 (3) | 0.0605 (8) | |
H11 | 1.6515 | 0.1830 | 0.8996 | 0.073* | |
C12 | 1.4789 (5) | 0.16640 (11) | 0.7448 (3) | 0.0637 (8) | |
H12 | 1.5847 | 0.1415 | 0.7185 | 0.076* | |
C13 | 1.2865 (5) | 0.17754 (11) | 0.6746 (3) | 0.0620 (8) | |
H13 | 1.2598 | 0.1601 | 0.6011 | 0.074* | |
C14 | 1.1343 (4) | 0.21375 (10) | 0.7112 (3) | 0.0539 (7) | |
H14 | 1.0035 | 0.2217 | 0.6622 | 0.065* | |
C15 | 0.0336 (4) | 0.42770 (9) | 0.7106 (2) | 0.0462 (6) | |
H15 | −0.0256 | 0.4450 | 0.7795 | 0.055* | |
C16 | −0.0728 (4) | 0.43521 (9) | 0.5962 (3) | 0.0454 (6) | |
C17 | −0.1442 (4) | 0.44076 (9) | 0.4942 (3) | 0.0452 (6) | |
C18 | −0.2073 (4) | 0.44766 (9) | 0.3686 (2) | 0.0411 (6) | |
C19 | −0.0521 (4) | 0.43317 (10) | 0.2787 (3) | 0.0503 (7) | |
H19 | 0.0906 | 0.4177 | 0.3005 | 0.060* | |
C20 | −0.1031 (5) | 0.44101 (11) | 0.1563 (3) | 0.0594 (8) | |
H20 | 0.0051 | 0.4314 | 0.0948 | 0.071* | |
C21 | −0.3104 (5) | 0.46277 (11) | 0.1255 (3) | 0.0573 (8) | |
H21 | −0.3454 | 0.4682 | 0.0421 | 0.069* | |
C22 | −0.4666 (4) | 0.47669 (10) | 0.2128 (3) | 0.0553 (7) | |
H22 | −0.6100 | 0.4916 | 0.1899 | 0.066* | |
C23 | −0.4185 (4) | 0.46941 (10) | 0.3345 (3) | 0.0488 (7) | |
H23 | −0.5287 | 0.4792 | 0.3950 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0676 (11) | 0.0593 (12) | 0.0370 (11) | 0.0160 (9) | −0.0094 (8) | −0.0083 (9) |
C1 | 0.0442 (13) | 0.0405 (14) | 0.0350 (14) | −0.0017 (11) | 0.0011 (11) | −0.0018 (11) |
C2 | 0.0393 (12) | 0.0397 (14) | 0.0385 (14) | −0.0018 (11) | −0.0056 (11) | −0.0005 (11) |
C3 | 0.0496 (13) | 0.0512 (16) | 0.0386 (15) | 0.0019 (12) | −0.0051 (11) | −0.0030 (12) |
C4 | 0.0601 (16) | 0.088 (2) | 0.0401 (16) | 0.0195 (16) | −0.0116 (13) | −0.0083 (16) |
C5 | 0.0421 (12) | 0.0454 (14) | 0.0328 (13) | −0.0017 (11) | −0.0069 (10) | 0.0012 (11) |
C6 | 0.0489 (13) | 0.0464 (15) | 0.0416 (15) | 0.0023 (12) | −0.0082 (12) | −0.0032 (12) |
C7 | 0.0421 (13) | 0.0522 (16) | 0.0419 (15) | 0.0009 (13) | −0.0100 (11) | 0.0008 (13) |
C8 | 0.0422 (13) | 0.0509 (16) | 0.0438 (15) | −0.0028 (13) | −0.0092 (11) | 0.0034 (13) |
C9 | 0.0432 (13) | 0.0407 (14) | 0.0422 (15) | −0.0032 (11) | −0.0009 (11) | 0.0048 (12) |
C10 | 0.0527 (15) | 0.0538 (17) | 0.0445 (16) | 0.0018 (13) | −0.0045 (12) | 0.0050 (13) |
C11 | 0.0592 (16) | 0.0630 (19) | 0.059 (2) | 0.0146 (15) | 0.0024 (14) | 0.0166 (16) |
C12 | 0.0734 (19) | 0.0492 (18) | 0.068 (2) | 0.0116 (15) | 0.0148 (17) | 0.0068 (16) |
C13 | 0.0739 (19) | 0.0573 (18) | 0.0546 (19) | −0.0060 (16) | 0.0033 (16) | −0.0134 (15) |
C14 | 0.0528 (15) | 0.0570 (17) | 0.0520 (18) | −0.0025 (14) | −0.0049 (13) | −0.0069 (14) |
C15 | 0.0502 (14) | 0.0456 (15) | 0.0430 (16) | 0.0017 (12) | −0.0098 (11) | −0.0019 (12) |
C16 | 0.0483 (14) | 0.0418 (15) | 0.0462 (17) | 0.0036 (11) | −0.0151 (12) | 0.0012 (12) |
C17 | 0.0434 (13) | 0.0420 (14) | 0.0505 (17) | 0.0018 (11) | −0.0138 (12) | −0.0003 (13) |
C18 | 0.0379 (12) | 0.0403 (14) | 0.0453 (16) | −0.0031 (11) | −0.0139 (11) | −0.0014 (12) |
C19 | 0.0396 (13) | 0.0560 (17) | 0.0555 (18) | 0.0008 (12) | −0.0102 (12) | −0.0050 (14) |
C20 | 0.0580 (17) | 0.069 (2) | 0.0512 (19) | −0.0082 (15) | 0.0041 (14) | −0.0093 (16) |
C21 | 0.0654 (18) | 0.0654 (19) | 0.0413 (16) | −0.0139 (15) | −0.0199 (14) | 0.0037 (15) |
C22 | 0.0502 (15) | 0.0617 (19) | 0.0545 (19) | 0.0036 (14) | −0.0229 (14) | 0.0064 (15) |
C23 | 0.0409 (13) | 0.0570 (17) | 0.0486 (16) | 0.0036 (12) | −0.0106 (11) | −0.0035 (14) |
O1—C1 | 1.230 (3) | C11—C12 | 1.373 (4) |
C1—C2 | 1.473 (3) | C12—H12 | 0.9500 |
C1—C5 | 1.471 (4) | C12—C13 | 1.382 (4) |
C2—C3 | 1.501 (4) | C13—H13 | 0.9500 |
C2—C6 | 1.345 (3) | C13—C14 | 1.371 (4) |
C3—H3A | 0.9900 | C14—H14 | 0.9500 |
C3—H3B | 0.9900 | C15—H15 | 0.9500 |
C3—C4 | 1.541 (4) | C15—C16 | 1.415 (4) |
C4—H4A | 0.9900 | C16—C17 | 1.204 (4) |
C4—H4B | 0.9900 | C17—C18 | 1.442 (4) |
C4—C5 | 1.494 (4) | C18—C19 | 1.379 (4) |
C5—C15 | 1.341 (3) | C18—C23 | 1.398 (3) |
C6—H6 | 0.9500 | C19—H19 | 0.9500 |
C6—C7 | 1.413 (4) | C19—C20 | 1.394 (4) |
C7—C8 | 1.198 (3) | C20—H20 | 0.9500 |
C8—C9 | 1.430 (4) | C20—C21 | 1.370 (4) |
C9—C10 | 1.399 (4) | C21—H21 | 0.9500 |
C9—C14 | 1.394 (4) | C21—C22 | 1.359 (4) |
C10—H10 | 0.9500 | C22—H22 | 0.9500 |
C10—C11 | 1.379 (4) | C22—C23 | 1.381 (4) |
C11—H11 | 0.9500 | C23—H23 | 0.9500 |
O1—C1—C2 | 125.5 (2) | C12—C11—H11 | 120.1 |
O1—C1—C5 | 126.4 (2) | C11—C12—H12 | 119.6 |
C5—C1—C2 | 108.1 (2) | C11—C12—C13 | 120.8 (3) |
C1—C2—C3 | 109.3 (2) | C13—C12—H12 | 119.6 |
C6—C2—C1 | 123.7 (2) | C12—C13—H13 | 120.0 |
C6—C2—C3 | 126.9 (2) | C14—C13—C12 | 120.0 (3) |
C2—C3—H3A | 110.5 | C14—C13—H13 | 120.0 |
C2—C3—H3B | 110.5 | C9—C14—H14 | 119.9 |
C2—C3—C4 | 106.4 (2) | C13—C14—C9 | 120.2 (3) |
H3A—C3—H3B | 108.6 | C13—C14—H14 | 119.9 |
C4—C3—H3A | 110.5 | C5—C15—H15 | 118.9 |
C4—C3—H3B | 110.5 | C5—C15—C16 | 122.1 (2) |
C3—C4—H4A | 110.5 | C16—C15—H15 | 118.9 |
C3—C4—H4B | 110.5 | C17—C16—C15 | 174.2 (3) |
H4A—C4—H4B | 108.7 | C16—C17—C18 | 174.7 (3) |
C5—C4—C3 | 106.2 (2) | C19—C18—C17 | 118.9 (2) |
C5—C4—H4A | 110.5 | C19—C18—C23 | 118.8 (3) |
C5—C4—H4B | 110.5 | C23—C18—C17 | 122.3 (2) |
C1—C5—C4 | 109.9 (2) | C18—C19—H19 | 119.7 |
C15—C5—C1 | 124.1 (2) | C18—C19—C20 | 120.5 (2) |
C15—C5—C4 | 126.0 (2) | C20—C19—H19 | 119.7 |
C2—C6—H6 | 118.7 | C19—C20—H20 | 120.2 |
C2—C6—C7 | 122.5 (2) | C21—C20—C19 | 119.5 (3) |
C7—C6—H6 | 118.7 | C21—C20—H20 | 120.2 |
C8—C7—C6 | 175.8 (3) | C20—C21—H21 | 119.6 |
C7—C8—C9 | 175.7 (3) | C22—C21—C20 | 120.7 (3) |
C10—C9—C8 | 121.3 (2) | C22—C21—H21 | 119.6 |
C14—C9—C8 | 119.5 (2) | C21—C22—H22 | 119.7 |
C14—C9—C10 | 119.1 (2) | C21—C22—C23 | 120.6 (3) |
C9—C10—H10 | 119.9 | C23—C22—H22 | 119.7 |
C11—C10—C9 | 120.2 (3) | C18—C23—H23 | 120.0 |
C11—C10—H10 | 119.9 | C22—C23—C18 | 119.9 (3) |
C10—C11—H11 | 120.1 | C22—C23—H23 | 120.0 |
C12—C11—C10 | 119.7 (3) | ||
O1—C1—C2—C3 | 176.7 (2) | C8—C9—C10—C11 | −178.5 (2) |
O1—C1—C2—C6 | −4.7 (4) | C8—C9—C14—C13 | 179.1 (2) |
O1—C1—C5—C4 | −178.4 (2) | C9—C10—C11—C12 | −0.1 (4) |
O1—C1—C5—C15 | 2.6 (4) | C10—C9—C14—C13 | 0.8 (4) |
C1—C2—C3—C4 | 3.4 (3) | C10—C11—C12—C13 | −0.1 (4) |
C1—C2—C6—C7 | 177.8 (2) | C11—C12—C13—C14 | 0.7 (4) |
C1—C5—C15—C16 | 176.3 (2) | C12—C13—C14—C9 | −1.0 (4) |
C2—C1—C5—C4 | 1.1 (3) | C14—C9—C10—C11 | −0.2 (4) |
C2—C1—C5—C15 | −178.0 (2) | C17—C18—C19—C20 | −177.5 (2) |
C2—C3—C4—C5 | −2.7 (3) | C17—C18—C23—C22 | 177.7 (2) |
C3—C2—C6—C7 | −3.7 (4) | C18—C19—C20—C21 | −0.8 (4) |
C3—C4—C5—C1 | 1.0 (3) | C19—C18—C23—C22 | −1.0 (4) |
C3—C4—C5—C15 | −180.0 (2) | C19—C20—C21—C22 | −0.1 (4) |
C4—C5—C15—C16 | −2.6 (4) | C20—C21—C22—C23 | 0.4 (4) |
C5—C1—C2—C3 | −2.8 (3) | C21—C22—C23—C18 | 0.2 (4) |
C5—C1—C2—C6 | 175.9 (2) | C23—C18—C19—C20 | 1.3 (4) |
C6—C2—C3—C4 | −175.2 (2) |
C23H14Br2O | Dx = 1.665 Mg m−3 |
Mr = 466.16 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Abm2 | Cell parameters from 6354 reflections |
a = 7.098 (3) Å | θ = 2–31° |
b = 42.72 (2) Å | µ = 4.37 mm−1 |
c = 6.135 (3) Å | T = 120 K |
V = 1860.1 (15) Å3 | Needle, yellow |
Z = 4 | 0.1 × 0.08 × 0.07 mm |
F(000) = 920 |
Bruker SMART APEX CCD area detector diffractometer | 1928 reflections with I > 2σ(I) |
phi and ω scans | Rint = 0.088 |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | θmax = 30.5°, θmin = 1.9° |
Tmin = 0.664, Tmax = 0.737 | h = −10→10 |
9371 measured reflections | k = −59→60 |
2642 independent reflections | l = −8→7 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.064 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.165 | (Δ/σ)max = 0.001 |
S = 0.97 | Δρmax = 1.93 e Å−3 |
2642 reflections | Δρmin = −1.09 e Å−3 |
121 parameters | Absolute structure: Flack x determined using 608 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
1 restraint | Absolute structure parameter: 0.30 (2) |
Primary atom site location: dual |
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 | ||
Br2 | 0.20037 (10) | 0.52932 (2) | −0.27597 (19) | 0.0254 (2) | |
C20 | 0.1758 (11) | 0.5942 (2) | −0.1799 (16) | 0.0211 (17) | |
H20 | 0.1250 | 0.5963 | −0.3225 | 0.025* | |
C19 | 0.2287 (12) | 0.56488 (19) | −0.0978 (15) | 0.0180 (16) | |
C9 | 0.2839 (11) | 0.6441 (2) | 0.3037 (16) | 0.0215 (17) | |
C16 | 0.2694 (11) | 0.61730 (19) | 0.1658 (13) | 0.0181 (17) | |
C21 | 0.2001 (11) | 0.62021 (19) | −0.0451 (15) | 0.0195 (16) | |
H21 | 0.1686 | 0.6404 | −0.0988 | 0.023* | |
C17 | 0.3224 (9) | 0.58749 (17) | 0.2436 (18) | 0.0176 (15) | |
H17 | 0.3737 | 0.5853 | 0.3858 | 0.021* | |
C7 | 0.3169 (12) | 0.6929 (2) | 0.5574 (14) | 0.0191 (16) | |
H7 | 0.3678 | 0.6905 | 0.6997 | 0.023* | |
C18 | 0.2993 (11) | 0.56113 (19) | 0.1114 (14) | 0.0192 (15) | |
H18 | 0.3315 | 0.5409 | 0.1640 | 0.023* | |
C8 | 0.2953 (13) | 0.6661 (2) | 0.4269 (17) | 0.0252 (19) | |
O1 | 0.3698 (13) | 0.7500 | 0.8151 (15) | 0.022 (2) | |
C5 | 0.3090 (15) | 0.7500 | 0.626 (2) | 0.014 (2) | |
C6 | 0.2691 (11) | 0.7219 (2) | 0.4905 (15) | 0.0177 (15) | |
C23 | 0.1891 (13) | 0.7318 (2) | 0.2744 (12) | 0.026 (2) | |
H23A | 0.0593 | 0.7237 | 0.2567 | 0.031* | |
H23B | 0.2676 | 0.7237 | 0.1535 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br2 | 0.0244 (4) | 0.0226 (4) | 0.0291 (4) | −0.0021 (3) | −0.0013 (6) | −0.0085 (5) |
C20 | 0.015 (4) | 0.029 (4) | 0.019 (4) | −0.004 (3) | −0.003 (3) | 0.002 (3) |
C19 | 0.015 (4) | 0.021 (4) | 0.017 (4) | 0.003 (3) | 0.007 (3) | 0.000 (3) |
C9 | 0.018 (4) | 0.024 (4) | 0.023 (4) | 0.000 (3) | 0.004 (3) | 0.003 (3) |
C16 | 0.014 (3) | 0.022 (4) | 0.018 (4) | −0.007 (3) | 0.007 (3) | 0.000 (3) |
C21 | 0.015 (4) | 0.020 (4) | 0.024 (4) | −0.001 (3) | 0.005 (3) | 0.003 (3) |
C17 | 0.016 (3) | 0.025 (3) | 0.012 (4) | 0.001 (2) | −0.001 (3) | 0.000 (4) |
C7 | 0.019 (4) | 0.026 (4) | 0.013 (4) | 0.001 (3) | 0.002 (3) | −0.002 (3) |
C18 | 0.019 (4) | 0.019 (3) | 0.019 (4) | −0.001 (3) | 0.000 (3) | 0.000 (3) |
C8 | 0.026 (5) | 0.023 (4) | 0.027 (5) | 0.001 (4) | −0.001 (4) | 0.002 (3) |
O1 | 0.017 (5) | 0.033 (5) | 0.015 (4) | 0.000 | −0.001 (4) | 0.000 |
C5 | 0.007 (5) | 0.020 (5) | 0.014 (5) | 0.000 | 0.005 (4) | 0.000 |
C6 | 0.016 (3) | 0.027 (4) | 0.010 (4) | −0.006 (3) | −0.002 (3) | 0.001 (3) |
C23 | 0.039 (5) | 0.032 (4) | 0.007 (4) | −0.002 (4) | −0.005 (3) | 0.000 (3) |
Br2—C19 | 1.882 (8) | C7—H7 | 0.9500 |
C20—H20 | 0.9500 | C7—C8 | 1.406 (12) |
C20—C19 | 1.400 (12) | C7—C6 | 1.346 (12) |
C20—C21 | 1.397 (12) | C18—H18 | 0.9500 |
C19—C18 | 1.387 (12) | O1—C5 | 1.237 (14) |
C9—C16 | 1.427 (12) | C5—C6 | 1.489 (12) |
C9—C8 | 1.209 (13) | C5—C6i | 1.489 (12) |
C16—C21 | 1.390 (12) | C6—C23 | 1.503 (12) |
C16—C17 | 1.411 (11) | C23—C23i | 1.556 (18) |
C21—H21 | 0.9500 | C23—H23A | 0.9900 |
C17—H17 | 0.9500 | C23—H23B | 0.9900 |
C17—C18 | 1.398 (12) | ||
C19—C20—H20 | 121.1 | C6—C7—C8 | 123.2 (8) |
C21—C20—H20 | 121.1 | C19—C18—C17 | 119.1 (8) |
C21—C20—C19 | 117.7 (8) | C19—C18—H18 | 120.4 |
C20—C19—Br2 | 118.9 (7) | C17—C18—H18 | 120.4 |
C18—C19—Br2 | 118.9 (6) | C9—C8—C7 | 175.5 (10) |
C18—C19—C20 | 122.2 (8) | O1—C5—C6i | 126.1 (6) |
C8—C9—C16 | 177.7 (10) | O1—C5—C6 | 126.1 (6) |
C21—C16—C9 | 120.4 (8) | C6—C5—C6i | 107.7 (11) |
C21—C16—C17 | 119.3 (8) | C7—C6—C5 | 121.6 (8) |
C17—C16—C9 | 120.3 (8) | C7—C6—C23 | 128.5 (8) |
C20—C21—H21 | 119.2 | C5—C6—C23 | 109.7 (8) |
C16—C21—C20 | 121.6 (8) | C6—C23—C23i | 106.4 (5) |
C16—C21—H21 | 119.2 | C6—C23—H23A | 110.5 |
C16—C17—H17 | 120.0 | C6—C23—H23B | 110.5 |
C18—C17—C16 | 120.0 (9) | C23i—C23—H23A | 110.5 |
C18—C17—H17 | 120.0 | C23i—C23—H23B | 110.5 |
C8—C7—H7 | 118.4 | H23A—C23—H23B | 108.6 |
C6—C7—H7 | 118.4 |
Symmetry code: (i) x, −y+3/2, z. |
C24H18O | F(000) = 680 |
Mr = 322.38 | Dx = 1.231 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 5.498 (4) Å | Cell parameters from 160 reflections |
b = 27.52 (2) Å | θ = 3.5–19.9° |
c = 13.885 (9) Å | µ = 0.07 mm−1 |
β = 124.09 (3)° | T = 120 K |
V = 1740 (2) Å3 | Needle, orange |
Z = 4 | 0.5 × 0.01 × 0.01 mm |
Bruker SMART APEX CCD area detector diffractometer | 2379 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.250 |
phi and ω scans | θmax = 30.8°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | h = −7→7 |
Tmin = 0.549, Tmax = 0.892 | k = −39→39 |
31410 measured reflections | l = −19→19 |
5336 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.085 | H-atom parameters constrained |
wR(F2) = 0.131 | w = 1/[σ2(Fo2) + (0.010P)2 + 0.2P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
5336 reflections | Δρmax = 0.35 e Å−3 |
226 parameters | Δρmin = −0.29 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 | 0.2215 (3) | 0.38803 (5) | 0.43170 (12) | 0.0283 (4) | |
C1 | −0.0203 (5) | 0.49168 (8) | 0.69236 (19) | 0.0253 (5) | |
C2 | 0.0487 (5) | 0.46686 (8) | 0.64072 (19) | 0.0255 (5) | |
C3 | 0.1269 (5) | 0.43898 (8) | 0.57618 (19) | 0.0246 (5) | |
H3 | 0.0025 | 0.4413 | 0.4938 | 0.030* | |
C4 | 0.3596 (5) | 0.40976 (7) | 0.62070 (18) | 0.0215 (5) | |
C5 | 0.3993 (5) | 0.38318 (7) | 0.53697 (18) | 0.0213 (5) | |
C6 | 0.6545 (4) | 0.35037 (7) | 0.58313 (18) | 0.0208 (5) | |
C7 | 0.6980 (5) | 0.32912 (8) | 0.50745 (18) | 0.0242 (5) | |
H7 | 0.5634 | 0.3365 | 0.4274 | 0.029* | |
C8 | 0.9293 (5) | 0.29653 (8) | 0.53765 (18) | 0.0256 (5) | |
C9 | 1.1210 (5) | 0.26811 (8) | 0.56295 (18) | 0.0260 (5) | |
C10 | −0.0992 (5) | 0.52097 (8) | 0.75603 (19) | 0.0245 (5) | |
C11 | −0.3717 (5) | 0.54333 (8) | 0.7005 (2) | 0.0289 (6) | |
H11 | −0.5068 | 0.5396 | 0.6189 | 0.035* | |
C12 | −0.4488 (5) | 0.57078 (8) | 0.7620 (2) | 0.0350 (6) | |
H12 | −0.6372 | 0.5856 | 0.7230 | 0.042* | |
C13 | −0.2541 (6) | 0.57689 (9) | 0.8797 (2) | 0.0408 (7) | |
H13 | −0.3068 | 0.5963 | 0.9219 | 0.049* | |
C14 | 0.0170 (6) | 0.55503 (10) | 0.9364 (2) | 0.0468 (7) | |
H14 | 0.1506 | 0.5591 | 1.0180 | 0.056* | |
C15 | 0.0961 (6) | 0.52717 (9) | 0.8753 (2) | 0.0387 (7) | |
H15 | 0.2842 | 0.5122 | 0.9149 | 0.046* | |
C16 | 1.3528 (5) | 0.23453 (7) | 0.59615 (19) | 0.0233 (5) | |
C17 | 1.3961 (5) | 0.21501 (8) | 0.5141 (2) | 0.0287 (6) | |
H17 | 1.2690 | 0.2239 | 0.4346 | 0.034* | |
C18 | 1.6227 (5) | 0.18283 (8) | 0.5479 (2) | 0.0346 (6) | |
H18 | 1.6492 | 0.1694 | 0.4913 | 0.042* | |
C19 | 1.8114 (5) | 0.16999 (8) | 0.6633 (2) | 0.0349 (6) | |
H19 | 1.9683 | 0.1480 | 0.6863 | 0.042* | |
C20 | 1.7708 (5) | 0.18927 (8) | 0.7450 (2) | 0.0334 (6) | |
H20 | 1.9007 | 0.1805 | 0.8244 | 0.040* | |
C21 | 1.5450 (5) | 0.22091 (8) | 0.71255 (19) | 0.0296 (6) | |
H21 | 1.5187 | 0.2337 | 0.7697 | 0.036* | |
C22 | 0.8584 (5) | 0.34230 (9) | 0.71298 (17) | 0.0278 (5) | |
H22A | 1.0310 | 0.3639 | 0.7447 | 0.033* | |
H22B | 0.9296 | 0.3083 | 0.7276 | 0.033* | |
C23 | 0.7109 (5) | 0.35207 (8) | 0.77629 (18) | 0.0284 (6) | |
H23A | 0.5543 | 0.3277 | 0.7524 | 0.034* | |
H23B | 0.8569 | 0.3488 | 0.8611 | 0.034* | |
C24 | 0.5798 (5) | 0.40236 (8) | 0.74956 (17) | 0.0255 (5) | |
H24A | 0.7387 | 0.4267 | 0.7786 | 0.031* | |
H24B | 0.4819 | 0.4076 | 0.7907 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0244 (9) | 0.0315 (9) | 0.0193 (8) | 0.0037 (7) | 0.0062 (7) | 0.0010 (7) |
C1 | 0.0206 (12) | 0.0252 (12) | 0.0255 (12) | 0.0021 (10) | 0.0100 (10) | 0.0048 (10) |
C2 | 0.0177 (12) | 0.0262 (13) | 0.0251 (12) | 0.0036 (10) | 0.0075 (10) | 0.0033 (10) |
C3 | 0.0238 (13) | 0.0232 (12) | 0.0217 (11) | 0.0001 (10) | 0.0096 (10) | 0.0011 (10) |
C4 | 0.0194 (12) | 0.0209 (12) | 0.0218 (11) | −0.0016 (10) | 0.0102 (10) | 0.0006 (9) |
C5 | 0.0181 (12) | 0.0195 (11) | 0.0234 (12) | −0.0030 (10) | 0.0099 (10) | 0.0007 (9) |
C6 | 0.0171 (11) | 0.0206 (11) | 0.0224 (11) | 0.0001 (10) | 0.0096 (10) | 0.0037 (10) |
C7 | 0.0210 (12) | 0.0244 (12) | 0.0219 (12) | 0.0009 (10) | 0.0088 (10) | 0.0005 (10) |
C8 | 0.0269 (13) | 0.0280 (13) | 0.0209 (12) | −0.0022 (11) | 0.0128 (11) | 0.0000 (10) |
C9 | 0.0289 (14) | 0.0266 (13) | 0.0231 (12) | −0.0027 (11) | 0.0150 (11) | 0.0004 (10) |
C10 | 0.0232 (13) | 0.0238 (12) | 0.0271 (12) | −0.0023 (10) | 0.0145 (11) | 0.0001 (10) |
C11 | 0.0214 (13) | 0.0322 (14) | 0.0284 (12) | −0.0025 (11) | 0.0112 (11) | −0.0039 (11) |
C12 | 0.0272 (14) | 0.0322 (14) | 0.0474 (16) | −0.0024 (11) | 0.0219 (13) | −0.0068 (12) |
C13 | 0.0507 (18) | 0.0389 (16) | 0.0488 (17) | −0.0095 (14) | 0.0377 (15) | −0.0128 (13) |
C14 | 0.0494 (19) | 0.0605 (19) | 0.0235 (13) | −0.0034 (15) | 0.0162 (13) | −0.0085 (13) |
C15 | 0.0321 (15) | 0.0457 (16) | 0.0291 (14) | 0.0074 (13) | 0.0115 (12) | 0.0024 (12) |
C16 | 0.0231 (13) | 0.0202 (12) | 0.0270 (12) | −0.0003 (10) | 0.0144 (11) | −0.0002 (10) |
C17 | 0.0299 (14) | 0.0298 (13) | 0.0272 (13) | −0.0013 (11) | 0.0164 (11) | −0.0022 (11) |
C18 | 0.0398 (16) | 0.0328 (14) | 0.0409 (15) | −0.0021 (12) | 0.0285 (13) | −0.0080 (12) |
C19 | 0.0284 (14) | 0.0247 (13) | 0.0535 (17) | 0.0047 (11) | 0.0241 (13) | 0.0001 (12) |
C20 | 0.0346 (15) | 0.0272 (13) | 0.0317 (13) | 0.0056 (11) | 0.0144 (12) | 0.0045 (11) |
C21 | 0.0395 (15) | 0.0239 (12) | 0.0271 (13) | 0.0015 (11) | 0.0197 (12) | 0.0000 (10) |
C22 | 0.0219 (12) | 0.0377 (14) | 0.0193 (11) | 0.0063 (11) | 0.0088 (10) | 0.0052 (10) |
C23 | 0.0259 (13) | 0.0347 (14) | 0.0206 (12) | 0.0023 (11) | 0.0107 (10) | 0.0026 (10) |
C24 | 0.0226 (13) | 0.0298 (13) | 0.0198 (11) | −0.0033 (10) | 0.0093 (10) | −0.0026 (10) |
O1—C5 | 1.228 (2) | C14—H14 | 0.9500 |
C1—C2 | 1.195 (3) | C14—C15 | 1.383 (3) |
C1—C10 | 1.432 (3) | C15—H15 | 0.9500 |
C2—C3 | 1.417 (3) | C16—C17 | 1.396 (3) |
C3—H3 | 0.9500 | C16—C21 | 1.398 (3) |
C3—C4 | 1.334 (3) | C17—H17 | 0.9500 |
C4—C5 | 1.489 (3) | C17—C18 | 1.379 (3) |
C4—C24 | 1.510 (3) | C18—H18 | 0.9500 |
C5—C6 | 1.479 (3) | C18—C19 | 1.380 (3) |
C6—C7 | 1.336 (3) | C19—H19 | 0.9500 |
C6—C22 | 1.514 (3) | C19—C20 | 1.379 (3) |
C7—H7 | 0.9500 | C20—H20 | 0.9500 |
C7—C8 | 1.414 (3) | C20—C21 | 1.370 (3) |
C8—C9 | 1.196 (3) | C21—H21 | 0.9500 |
C9—C16 | 1.425 (3) | C22—H22A | 0.9900 |
C10—C11 | 1.387 (3) | C22—H22B | 0.9900 |
C10—C15 | 1.390 (3) | C22—C23 | 1.517 (3) |
C11—H11 | 0.9500 | C23—H23A | 0.9900 |
C11—C12 | 1.373 (3) | C23—H23B | 0.9900 |
C12—H12 | 0.9500 | C23—C24 | 1.508 (3) |
C12—C13 | 1.372 (3) | C24—H24A | 0.9900 |
C13—H13 | 0.9500 | C24—H24B | 0.9900 |
C13—C14 | 1.374 (4) | ||
C2—C1—C10 | 179.0 (3) | C17—C16—C9 | 121.1 (2) |
C1—C2—C3 | 177.7 (2) | C17—C16—C21 | 118.5 (2) |
C2—C3—H3 | 117.1 | C21—C16—C9 | 120.5 (2) |
C4—C3—C2 | 125.8 (2) | C16—C17—H17 | 119.9 |
C4—C3—H3 | 117.1 | C18—C17—C16 | 120.3 (2) |
C3—C4—C5 | 117.1 (2) | C18—C17—H17 | 119.9 |
C3—C4—C24 | 123.6 (2) | C17—C18—H18 | 119.7 |
C5—C4—C24 | 119.21 (19) | C17—C18—C19 | 120.5 (2) |
O1—C5—C4 | 120.6 (2) | C19—C18—H18 | 119.7 |
O1—C5—C6 | 120.7 (2) | C18—C19—H19 | 120.2 |
C6—C5—C4 | 118.68 (19) | C20—C19—C18 | 119.6 (2) |
C5—C6—C22 | 119.67 (19) | C20—C19—H19 | 120.2 |
C7—C6—C5 | 118.09 (19) | C19—C20—H20 | 119.7 |
C7—C6—C22 | 122.2 (2) | C21—C20—C19 | 120.6 (2) |
C6—C7—H7 | 117.6 | C21—C20—H20 | 119.7 |
C6—C7—C8 | 124.9 (2) | C16—C21—H21 | 119.7 |
C8—C7—H7 | 117.6 | C20—C21—C16 | 120.6 (2) |
C9—C8—C7 | 178.5 (2) | C20—C21—H21 | 119.7 |
C8—C9—C16 | 178.5 (2) | C6—C22—H22A | 109.1 |
C11—C10—C1 | 120.9 (2) | C6—C22—H22B | 109.1 |
C11—C10—C15 | 118.7 (2) | C6—C22—C23 | 112.64 (19) |
C15—C10—C1 | 120.4 (2) | H22A—C22—H22B | 107.8 |
C10—C11—H11 | 119.6 | C23—C22—H22A | 109.1 |
C12—C11—C10 | 120.8 (2) | C23—C22—H22B | 109.1 |
C12—C11—H11 | 119.6 | C22—C23—H23A | 109.5 |
C11—C12—H12 | 120.0 | C22—C23—H23B | 109.5 |
C13—C12—C11 | 120.1 (2) | H23A—C23—H23B | 108.0 |
C13—C12—H12 | 120.0 | C24—C23—C22 | 110.91 (19) |
C12—C13—H13 | 120.0 | C24—C23—H23A | 109.5 |
C12—C13—C14 | 120.1 (2) | C24—C23—H23B | 109.5 |
C14—C13—H13 | 120.0 | C4—C24—H24A | 109.3 |
C13—C14—H14 | 119.9 | C4—C24—H24B | 109.3 |
C13—C14—C15 | 120.2 (2) | C23—C24—C4 | 111.74 (18) |
C15—C14—H14 | 119.9 | C23—C24—H24A | 109.3 |
C10—C15—H15 | 120.0 | C23—C24—H24B | 109.3 |
C14—C15—C10 | 120.1 (2) | H24A—C24—H24B | 107.9 |
C14—C15—H15 | 120.0 |
C24H16Br2O | Dx = 1.589 Mg m−3 |
Mr = 480.19 | Synchrotron radiation, λ = 0.9699 Å |
Orthorhombic, Pca21 | Cell parameters from 3568 reflections |
a = 12.006 (2) Å | θ = 5.3–38.6° |
b = 5.2243 (10) Å | µ = 1.02 mm−1 |
c = 31.998 (6) Å | T = 100 K |
V = 2007.0 (7) Å3 | Needle, yellow |
Z = 4 | 0.15 × 0.01 × 0.01 mm |
F(000) = 952 |
Mar CCD diffractometer | 2569 reflections with I > 2σ(I) |
phi–scan | Rint = 0.129 |
Absorption correction: multi-scan (SCALA; Evans, 2006) | θmax = 38.4°, θmin = 4.6° |
h = −14→15 | |
9749 measured reflections | k = −6→6 |
3927 independent reflections | l = −38→39 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.079 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.258 | (Δ/σ)max = 0.012 |
S = 1.00 | Δρmax = 0.95 e Å−3 |
3927 reflections | Δρmin = −1.42 e Å−3 |
244 parameters | Absolute structure: Flack x determined using 812 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
1 restraint | Absolute structure parameter: 0.47 (7) |
Primary atom site location: dual |
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 | ||
Br1 | 0.94120 (15) | 1.6770 (3) | 0.72569 (5) | 0.0503 (5) | |
Br2 | 0.90419 (16) | −1.1722 (3) | 0.27438 (6) | 0.0516 (6) | |
O1 | 0.5159 (11) | 0.169 (2) | 0.5168 (4) | 0.069 (4) | |
C14 | 0.9401 (12) | 1.303 (3) | 0.6603 (6) | 0.046 (4) | |
H14 | 1.0171 | 1.3416 | 0.6581 | 0.056* | |
C15 | 0.8918 (13) | 1.123 (3) | 0.6339 (5) | 0.046 (3) | |
H15 | 0.9357 | 1.0400 | 0.6133 | 0.055* | |
C7 | 0.6106 (14) | −0.054 (3) | 0.4458 (5) | 0.055 (4) | |
H7 | 0.5319 | −0.0431 | 0.4485 | 0.066* | |
C17 | 0.6827 (14) | −0.661 (3) | 0.3295 (5) | 0.050 (4) | |
H17 | 0.6068 | −0.6144 | 0.3259 | 0.060* | |
C1 | 0.7256 (14) | 0.880 (3) | 0.6105 (5) | 0.051 (4) | |
C2 | 0.6796 (13) | 0.726 (3) | 0.5886 (5) | 0.050 (4) | |
C8 | 0.6544 (14) | −0.211 (3) | 0.4132 (5) | 0.050 (4) | |
C13 | 0.8740 (13) | 1.426 (3) | 0.6902 (4) | 0.044 (3) | |
C12 | 0.7614 (13) | 1.372 (3) | 0.6946 (5) | 0.046 (4) | |
H12 | 0.7168 | 1.4581 | 0.7147 | 0.055* | |
C16 | 0.7460 (13) | −0.544 (3) | 0.3607 (5) | 0.051 (4) | |
C9 | 0.6963 (15) | −0.357 (3) | 0.3885 (5) | 0.051 (4) | |
C20 | 0.9045 (16) | −0.802 (3) | 0.3399 (6) | 0.053 (4) | |
H20 | 0.9799 | −0.8532 | 0.3435 | 0.063* | |
C6 | 0.6735 (13) | 0.081 (3) | 0.4732 (6) | 0.050 (4) | |
C22 | 0.8056 (14) | 0.403 (3) | 0.5298 (5) | 0.051 (4) | |
H22A | 0.8405 | 0.2745 | 0.5484 | 0.061* | |
H22B | 0.8325 | 0.5742 | 0.5386 | 0.061* | |
C5 | 0.6153 (14) | 0.208 (3) | 0.5089 (6) | 0.054 (4) | |
C21 | 0.8582 (15) | −0.612 (3) | 0.3654 (5) | 0.051 (4) | |
H21 | 0.9028 | −0.5282 | 0.3858 | 0.061* | |
C10 | 0.7787 (13) | 1.064 (3) | 0.6377 (5) | 0.046 (3) | |
C4 | 0.6823 (13) | 0.392 (3) | 0.5350 (5) | 0.047 (3) | |
C3 | 0.6262 (15) | 0.546 (3) | 0.5621 (5) | 0.056 (4) | |
H3 | 0.5474 | 0.5322 | 0.5633 | 0.067* | |
C19 | 0.8392 (13) | −0.916 (3) | 0.3093 (5) | 0.051 (4) | |
C11 | 0.7173 (14) | 1.188 (3) | 0.6690 (6) | 0.057 (4) | |
H11 | 0.6413 | 1.1428 | 0.6725 | 0.068* | |
C18 | 0.7297 (14) | −0.847 (3) | 0.3036 (6) | 0.051 (4) | |
H18 | 0.6865 | −0.9253 | 0.2822 | 0.062* | |
C23 | 0.8424 (15) | 0.353 (3) | 0.4848 (6) | 0.057 (4) | |
H23A | 0.9247 | 0.3561 | 0.4831 | 0.068* | |
H23B | 0.8130 | 0.4893 | 0.4663 | 0.068* | |
C24 | 0.7985 (12) | 0.091 (3) | 0.4705 (5) | 0.049 (4) | |
H24A | 0.8220 | 0.0588 | 0.4413 | 0.059* | |
H24B | 0.8307 | −0.0454 | 0.4883 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0521 (10) | 0.0486 (10) | 0.0502 (10) | −0.0017 (7) | −0.0008 (9) | −0.0040 (11) |
Br2 | 0.0530 (10) | 0.0492 (10) | 0.0526 (11) | 0.0004 (7) | 0.0008 (9) | −0.0026 (11) |
O1 | 0.040 (7) | 0.086 (9) | 0.082 (9) | −0.001 (5) | 0.010 (6) | −0.033 (6) |
C14 | 0.033 (8) | 0.046 (9) | 0.060 (11) | 0.005 (6) | −0.001 (7) | 0.001 (7) |
C15 | 0.050 (9) | 0.051 (8) | 0.037 (8) | 0.004 (6) | 0.001 (7) | −0.006 (7) |
C7 | 0.054 (9) | 0.054 (10) | 0.056 (9) | 0.006 (7) | −0.009 (7) | −0.011 (8) |
C17 | 0.048 (9) | 0.056 (9) | 0.046 (9) | 0.000 (7) | 0.001 (7) | −0.007 (7) |
C1 | 0.061 (10) | 0.049 (8) | 0.042 (8) | 0.005 (7) | 0.004 (7) | 0.001 (7) |
C2 | 0.045 (9) | 0.048 (8) | 0.057 (11) | 0.001 (7) | 0.000 (7) | −0.016 (8) |
C8 | 0.046 (9) | 0.058 (9) | 0.046 (9) | −0.006 (7) | −0.003 (7) | 0.004 (8) |
C13 | 0.053 (8) | 0.038 (7) | 0.043 (8) | 0.005 (7) | 0.002 (6) | 0.009 (7) |
C12 | 0.049 (9) | 0.049 (8) | 0.040 (8) | 0.008 (7) | 0.004 (6) | −0.010 (7) |
C16 | 0.044 (8) | 0.056 (10) | 0.052 (9) | 0.000 (7) | 0.000 (7) | −0.001 (8) |
C9 | 0.053 (10) | 0.053 (9) | 0.048 (9) | −0.001 (7) | −0.001 (7) | −0.004 (7) |
C20 | 0.056 (11) | 0.050 (10) | 0.052 (11) | −0.001 (7) | −0.003 (8) | 0.009 (8) |
C6 | 0.044 (8) | 0.044 (8) | 0.063 (10) | 0.001 (7) | 0.004 (7) | −0.011 (8) |
C22 | 0.053 (9) | 0.047 (8) | 0.053 (9) | −0.009 (7) | 0.008 (7) | −0.004 (8) |
C5 | 0.040 (10) | 0.047 (9) | 0.075 (13) | 0.003 (6) | −0.004 (8) | −0.012 (8) |
C21 | 0.062 (10) | 0.042 (8) | 0.048 (9) | −0.003 (7) | −0.004 (8) | −0.004 (7) |
C10 | 0.059 (9) | 0.036 (7) | 0.042 (8) | 0.003 (7) | 0.007 (7) | 0.000 (7) |
C4 | 0.043 (8) | 0.046 (8) | 0.050 (9) | 0.004 (6) | 0.008 (6) | −0.005 (7) |
C3 | 0.050 (9) | 0.055 (9) | 0.063 (10) | −0.004 (7) | 0.006 (8) | −0.016 (8) |
C19 | 0.052 (9) | 0.053 (8) | 0.048 (9) | −0.012 (7) | −0.004 (7) | −0.004 (8) |
C11 | 0.043 (9) | 0.061 (10) | 0.066 (11) | −0.005 (7) | 0.013 (8) | −0.014 (8) |
C18 | 0.044 (9) | 0.051 (9) | 0.059 (10) | −0.004 (6) | −0.011 (8) | 0.007 (8) |
C23 | 0.048 (9) | 0.066 (10) | 0.056 (10) | −0.002 (7) | 0.004 (8) | −0.009 (8) |
C24 | 0.046 (8) | 0.045 (8) | 0.057 (10) | −0.004 (7) | −0.008 (7) | −0.012 (8) |
Br1—C13 | 1.913 (16) | C20—H20 | 0.9500 |
Br2—C19 | 1.912 (16) | C20—C21 | 1.40 (2) |
O1—C5 | 1.24 (2) | C20—C19 | 1.39 (2) |
C14—H14 | 0.9500 | C6—C5 | 1.49 (2) |
C14—C15 | 1.39 (2) | C6—C24 | 1.50 (2) |
C14—C13 | 1.40 (2) | C22—H22A | 0.9900 |
C15—H15 | 0.9500 | C22—H22B | 0.9900 |
C15—C10 | 1.40 (2) | C22—C4 | 1.49 (2) |
C7—H7 | 0.9500 | C22—C23 | 1.53 (2) |
C7—C8 | 1.43 (2) | C5—C4 | 1.51 (2) |
C7—C6 | 1.36 (2) | C21—H21 | 0.9500 |
C17—H17 | 0.9500 | C10—C11 | 1.40 (2) |
C17—C16 | 1.40 (2) | C4—C3 | 1.36 (2) |
C17—C18 | 1.40 (2) | C3—H3 | 0.9500 |
C1—C2 | 1.20 (2) | C19—C18 | 1.37 (2) |
C1—C10 | 1.45 (2) | C11—H11 | 0.9500 |
C2—C3 | 1.42 (2) | C18—H18 | 0.9500 |
C8—C9 | 1.21 (2) | C23—H23A | 0.9900 |
C13—C12 | 1.39 (2) | C23—H23B | 0.9900 |
C12—H12 | 0.9500 | C23—C24 | 1.54 (2) |
C12—C11 | 1.37 (2) | C24—H24A | 0.9900 |
C16—C9 | 1.45 (2) | C24—H24B | 0.9900 |
C16—C21 | 1.40 (2) | ||
C15—C14—H14 | 120.3 | O1—C5—C6 | 122.3 (15) |
C15—C14—C13 | 119.3 (14) | O1—C5—C4 | 120.5 (15) |
C13—C14—H14 | 120.3 | C6—C5—C4 | 117.2 (14) |
C14—C15—H15 | 119.9 | C16—C21—C20 | 119.8 (16) |
C14—C15—C10 | 120.1 (14) | C16—C21—H21 | 120.1 |
C10—C15—H15 | 119.9 | C20—C21—H21 | 120.1 |
C8—C7—H7 | 117.7 | C15—C10—C1 | 121.6 (13) |
C6—C7—H7 | 117.7 | C15—C10—C11 | 118.1 (14) |
C6—C7—C8 | 124.6 (15) | C11—C10—C1 | 120.3 (14) |
C16—C17—H17 | 119.7 | C22—C4—C5 | 119.6 (14) |
C16—C17—C18 | 120.6 (16) | C3—C4—C22 | 122.7 (15) |
C18—C17—H17 | 119.7 | C3—C4—C5 | 117.8 (14) |
C2—C1—C10 | 178.6 (18) | C2—C3—H3 | 118.4 |
C1—C2—C3 | 179.0 (19) | C4—C3—C2 | 123.3 (16) |
C9—C8—C7 | 173.8 (17) | C4—C3—H3 | 118.4 |
C14—C13—Br1 | 118.9 (11) | C20—C19—Br2 | 118.8 (13) |
C12—C13—Br1 | 119.4 (11) | C18—C19—Br2 | 119.7 (12) |
C12—C13—C14 | 121.8 (14) | C18—C19—C20 | 121.6 (15) |
C13—C12—H12 | 121.3 | C12—C11—C10 | 123.2 (15) |
C11—C12—C13 | 117.4 (14) | C12—C11—H11 | 118.4 |
C11—C12—H12 | 121.3 | C10—C11—H11 | 118.4 |
C17—C16—C9 | 120.7 (15) | C17—C18—H18 | 120.4 |
C17—C16—C21 | 119.4 (15) | C19—C18—C17 | 119.3 (16) |
C21—C16—C9 | 119.9 (15) | C19—C18—H18 | 120.4 |
C8—C9—C16 | 176.8 (17) | C22—C23—H23A | 109.8 |
C21—C20—H20 | 120.3 | C22—C23—H23B | 109.8 |
C19—C20—H20 | 120.3 | C22—C23—C24 | 109.5 (14) |
C19—C20—C21 | 119.3 (16) | H23A—C23—H23B | 108.2 |
C7—C6—C5 | 117.7 (14) | C24—C23—H23A | 109.8 |
C7—C6—C24 | 122.3 (14) | C24—C23—H23B | 109.8 |
C5—C6—C24 | 119.8 (14) | C6—C24—C23 | 110.7 (14) |
H22A—C22—H22B | 107.8 | C6—C24—H24A | 109.5 |
C4—C22—H22A | 109.1 | C6—C24—H24B | 109.5 |
C4—C22—H22B | 109.1 | C23—C24—H24A | 109.5 |
C4—C22—C23 | 112.6 (14) | C23—C24—H24B | 109.5 |
C23—C22—H22A | 109.1 | H24A—C24—H24B | 108.1 |
C23—C22—H22B | 109.1 |
C28H25O | F(000) = 804 |
Mr = 377.48 | Dx = 1.136 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.9422 (14) Å | Cell parameters from 3825 reflections |
b = 6.9614 (7) Å | θ = 2.8–30.5° |
c = 24.721 (3) Å | µ = 0.07 mm−1 |
β = 97.732 (2)° | T = 120 K |
V = 2207.0 (4) Å3 | Needle, yellow |
Z = 4 | 0.48 × 0.01 × 0.01 mm |
Bruker SMART APEX CCD area detector diffractometer | 6739 independent reflections |
Radiation source: sealed tube | 2902 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.165 |
Detector resolution: 8 pixels mm-1 | θmax = 30.6°, θmin = 1.7° |
ω and φ scans | h = −18→18 |
Absorption correction: multi-scan SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1821 before and 0.0591 after correction. The Ratio of minimum to maximum transmission is 0.5936. The λ/2 correction factor is 0.00150. | k = −9→9 |
Tmin = 0.443, Tmax = 0.746 | l = −35→35 |
36697 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.078 | H-atom parameters constrained |
wR(F2) = 0.163 | w = 1/[σ2(Fo2) + (0.050P)2 + 0.5P] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
6739 reflections | Δρmax = 0.41 e Å−3 |
304 parameters | Δρmin = −0.17 e Å−3 |
36 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.37750 (10) | 0.2693 (2) | 0.47019 (5) | 0.0430 (4) | |
C1 | 0.55701 (14) | 0.2194 (3) | 0.67830 (8) | 0.0338 (4) | |
C2 | 0.52205 (14) | 0.2311 (3) | 0.63087 (8) | 0.0367 (5) | |
C3 | 0.47789 (15) | 0.2434 (3) | 0.57535 (7) | 0.0389 (5) | |
H3 | 0.4041 | 0.2525 | 0.5676 | 0.047* | |
C4 | 0.53249 (14) | 0.2433 (3) | 0.53268 (7) | 0.0333 (4) | |
C5 | 0.47354 (14) | 0.2606 (3) | 0.47740 (7) | 0.0336 (4) | |
C6 | 0.53363 (14) | 0.2657 (3) | 0.43039 (7) | 0.0415 (5) | |
C7 | 0.48361 (14) | 0.2570 (3) | 0.38011 (7) | 0.0331 (4) | |
H7 | 0.4096 | 0.2511 | 0.3761 | 0.040* | |
C8 | 0.53114 (14) | 0.2557 (3) | 0.33169 (7) | 0.0335 (4) | |
C9 | 0.57153 (14) | 0.2512 (2) | 0.29079 (7) | 0.0323 (4) | |
C10 | 0.59790 (14) | 0.2086 (2) | 0.73488 (7) | 0.0313 (4) | |
C11 | 0.55096 (15) | 0.3125 (3) | 0.77338 (8) | 0.0384 (5) | |
H11 | 0.4908 | 0.3879 | 0.7619 | 0.046* | |
C12 | 0.59114 (16) | 0.3064 (3) | 0.82770 (8) | 0.0438 (5) | |
H12 | 0.5589 | 0.3781 | 0.8535 | 0.053* | |
C13 | 0.67802 (16) | 0.1966 (3) | 0.84486 (8) | 0.0440 (5) | |
H13 | 0.7063 | 0.1941 | 0.8824 | 0.053* | |
C14 | 0.72383 (15) | 0.0905 (3) | 0.80746 (8) | 0.0455 (5) | |
H14 | 0.7827 | 0.0124 | 0.8195 | 0.055* | |
C15 | 0.68492 (14) | 0.0967 (3) | 0.75281 (8) | 0.0390 (5) | |
H15 | 0.7176 | 0.0244 | 0.7273 | 0.047* | |
C16 | 0.64889 (14) | 0.2301 (3) | 0.54116 (8) | 0.0479 (5) | |
H16A | 0.6765 | 0.3435 | 0.5625 | 0.057* | |
H16B | 0.6689 | 0.1150 | 0.5636 | 0.057* | |
C17 | 0.70079 (15) | 0.2195 (4) | 0.49164 (8) | 0.0528 (6) | |
C19 | 0.61877 (14) | 0.2410 (2) | 0.24173 (7) | 0.0307 (4) | |
C20 | 0.56410 (15) | 0.1614 (3) | 0.19490 (8) | 0.0438 (5) | |
H20 | 0.4946 | 0.1178 | 0.1951 | 0.053* | |
C21 | 0.61104 (18) | 0.1457 (3) | 0.14801 (8) | 0.0574 (6) | |
H21 | 0.5739 | 0.0893 | 0.1162 | 0.069* | |
C22 | 0.71109 (18) | 0.2112 (3) | 0.14710 (9) | 0.0540 (6) | |
H22 | 0.7425 | 0.2014 | 0.1146 | 0.065* | |
C23 | 0.76561 (16) | 0.2908 (3) | 0.19325 (9) | 0.0480 (5) | |
H23 | 0.8347 | 0.3360 | 0.1925 | 0.058* | |
C24 | 0.72047 (15) | 0.3053 (3) | 0.24064 (8) | 0.0390 (5) | |
H24 | 0.7588 | 0.3591 | 0.2725 | 0.047* | |
C25 | 0.82077 (14) | 0.2134 (3) | 0.50075 (8) | 0.0430 (5) | |
C18 | 0.6479 (2) | 0.3162 (6) | 0.44357 (11) | 0.0436 (7) | 0.7 |
H18A | 0.6836 | 0.2830 | 0.4118 | 0.052* | 0.7 |
H18B | 0.6543 | 0.4567 | 0.4492 | 0.052* | 0.7 |
C26 | 0.8553 (3) | 0.4235 (6) | 0.50859 (15) | 0.0593 (11) | 0.6 |
H26A | 0.8313 | 0.4964 | 0.4753 | 0.089* | 0.6 |
H26B | 0.9315 | 0.4295 | 0.5161 | 0.089* | 0.6 |
H26C | 0.8251 | 0.4789 | 0.5394 | 0.089* | 0.6 |
C27 | 0.8630 (3) | 0.1323 (8) | 0.44951 (16) | 0.0693 (12) | 0.6 |
H27A | 0.8392 | −0.0005 | 0.4433 | 0.104* | 0.6 |
H27B | 0.9394 | 0.1353 | 0.4553 | 0.104* | 0.6 |
H27C | 0.8371 | 0.2108 | 0.4176 | 0.104* | 0.6 |
C28 | 0.8626 (3) | 0.0952 (7) | 0.55006 (16) | 0.0625 (11) | 0.6 |
H28A | 0.8408 | 0.1529 | 0.5829 | 0.094* | 0.6 |
H28B | 0.9389 | 0.0919 | 0.5537 | 0.094* | 0.6 |
H28C | 0.8352 | −0.0359 | 0.5457 | 0.094* | 0.6 |
C18A | 0.6494 (4) | 0.1728 (10) | 0.4419 (2) | 0.0265 (13) | 0.3 |
H18C | 0.6436 | 0.0312 | 0.4392 | 0.032* | 0.3 |
H18D | 0.6907 | 0.2173 | 0.4134 | 0.032* | 0.3 |
C26A | 0.8747 (5) | 0.2903 (12) | 0.5563 (3) | 0.079 (2) | 0.4 |
H26D | 0.8661 | 0.4300 | 0.5576 | 0.118* | 0.4 |
H26E | 0.9492 | 0.2589 | 0.5603 | 0.118* | 0.4 |
H26F | 0.8431 | 0.2307 | 0.5860 | 0.118* | 0.4 |
C27A | 0.8751 (5) | 0.3016 (11) | 0.4568 (3) | 0.0715 (19) | 0.4 |
H27D | 0.8464 | 0.2477 | 0.4213 | 0.107* | 0.4 |
H27E | 0.9499 | 0.2738 | 0.4641 | 0.107* | 0.4 |
H27F | 0.8643 | 0.4410 | 0.4564 | 0.107* | 0.4 |
C28A | 0.8410 (4) | −0.0044 (8) | 0.5024 (3) | 0.0574 (15) | 0.4 |
H28D | 0.7999 | −0.0647 | 0.5282 | 0.086* | 0.4 |
H28E | 0.9153 | −0.0285 | 0.5140 | 0.086* | 0.4 |
H28F | 0.8208 | −0.0587 | 0.4659 | 0.086* | 0.4 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0313 (7) | 0.0606 (9) | 0.0387 (8) | 0.0078 (7) | 0.0106 (6) | 0.0009 (6) |
C1 | 0.0375 (10) | 0.0309 (10) | 0.0363 (12) | −0.0036 (8) | 0.0175 (9) | −0.0015 (8) |
C2 | 0.0390 (11) | 0.0410 (12) | 0.0333 (11) | −0.0039 (9) | 0.0169 (9) | −0.0004 (9) |
C3 | 0.0368 (10) | 0.0483 (12) | 0.0339 (11) | 0.0001 (10) | 0.0128 (8) | 0.0012 (9) |
C4 | 0.0351 (10) | 0.0367 (11) | 0.0298 (10) | −0.0002 (9) | 0.0105 (8) | 0.0003 (8) |
C5 | 0.0328 (10) | 0.0371 (11) | 0.0324 (10) | 0.0048 (9) | 0.0105 (8) | 0.0018 (8) |
C6 | 0.0318 (10) | 0.0633 (14) | 0.0310 (11) | 0.0050 (10) | 0.0104 (8) | 0.0051 (9) |
C7 | 0.0325 (10) | 0.0338 (11) | 0.0332 (10) | 0.0071 (8) | 0.0058 (8) | 0.0024 (8) |
C8 | 0.0359 (10) | 0.0330 (11) | 0.0307 (10) | 0.0061 (9) | 0.0015 (8) | 0.0024 (8) |
C9 | 0.0362 (10) | 0.0276 (10) | 0.0326 (10) | 0.0031 (8) | 0.0030 (8) | 0.0030 (8) |
C10 | 0.0350 (10) | 0.0284 (10) | 0.0322 (10) | −0.0047 (8) | 0.0111 (8) | −0.0019 (8) |
C11 | 0.0417 (11) | 0.0366 (11) | 0.0379 (11) | 0.0064 (9) | 0.0094 (9) | −0.0001 (9) |
C12 | 0.0525 (13) | 0.0466 (13) | 0.0346 (11) | 0.0046 (10) | 0.0143 (10) | −0.0074 (9) |
C13 | 0.0482 (12) | 0.0477 (13) | 0.0351 (11) | −0.0008 (11) | 0.0020 (9) | −0.0023 (9) |
C14 | 0.0405 (12) | 0.0426 (12) | 0.0519 (14) | 0.0065 (10) | 0.0004 (10) | −0.0048 (10) |
C15 | 0.0381 (11) | 0.0405 (12) | 0.0402 (12) | 0.0016 (9) | 0.0119 (9) | −0.0102 (9) |
C16 | 0.0331 (11) | 0.0770 (16) | 0.0345 (11) | −0.0006 (11) | 0.0081 (8) | 0.0043 (10) |
C17 | 0.0287 (10) | 0.1027 (19) | 0.0285 (11) | 0.0149 (11) | 0.0098 (8) | 0.0147 (11) |
C19 | 0.0351 (10) | 0.0275 (10) | 0.0305 (10) | 0.0041 (8) | 0.0082 (8) | 0.0030 (8) |
C20 | 0.0388 (11) | 0.0545 (13) | 0.0385 (12) | −0.0057 (10) | 0.0063 (9) | −0.0026 (9) |
C21 | 0.0602 (15) | 0.0797 (18) | 0.0334 (12) | −0.0090 (13) | 0.0102 (10) | −0.0126 (11) |
C22 | 0.0618 (15) | 0.0611 (15) | 0.0439 (13) | −0.0021 (12) | 0.0250 (11) | −0.0062 (11) |
C23 | 0.0452 (12) | 0.0433 (13) | 0.0597 (14) | −0.0051 (10) | 0.0229 (11) | 0.0006 (10) |
C24 | 0.0422 (12) | 0.0336 (11) | 0.0414 (12) | −0.0029 (9) | 0.0069 (9) | −0.0044 (8) |
C25 | 0.0300 (10) | 0.0619 (14) | 0.0385 (11) | 0.0029 (10) | 0.0093 (8) | 0.0091 (10) |
C18 | 0.0341 (17) | 0.063 (2) | 0.0356 (17) | 0.0014 (17) | 0.0129 (13) | 0.0104 (16) |
C26 | 0.0322 (19) | 0.089 (3) | 0.057 (2) | −0.0208 (19) | 0.0070 (17) | 0.016 (2) |
C27 | 0.042 (2) | 0.103 (3) | 0.068 (3) | 0.025 (2) | 0.0232 (19) | 0.004 (3) |
C28 | 0.035 (2) | 0.090 (3) | 0.062 (3) | 0.017 (2) | 0.0027 (18) | 0.031 (2) |
C18A | 0.019 (3) | 0.027 (3) | 0.035 (4) | 0.002 (3) | 0.013 (3) | −0.009 (3) |
C26A | 0.049 (3) | 0.105 (5) | 0.080 (4) | −0.008 (4) | 0.000 (3) | −0.025 (4) |
C27A | 0.041 (3) | 0.084 (4) | 0.093 (4) | −0.004 (3) | 0.021 (3) | 0.023 (4) |
C28A | 0.033 (3) | 0.062 (4) | 0.077 (4) | 0.009 (3) | 0.012 (3) | 0.004 (3) |
O1—C5 | 1.233 (2) | C20—C21 | 1.384 (3) |
C1—C2 | 1.201 (2) | C21—H21 | 0.9500 |
C1—C10 | 1.430 (3) | C21—C22 | 1.376 (3) |
C2—C3 | 1.416 (3) | C22—H22 | 0.9500 |
C3—H3 | 0.9500 | C22—C23 | 1.375 (3) |
C3—C4 | 1.346 (2) | C23—H23 | 0.9500 |
C4—C5 | 1.478 (2) | C23—C24 | 1.381 (3) |
C4—C16 | 1.496 (2) | C24—H24 | 0.9500 |
C5—C6 | 1.483 (2) | C25—C26 | 1.534 (4) |
C6—C7 | 1.323 (2) | C25—C27 | 1.552 (4) |
C6—C18 | 1.513 (3) | C25—C28 | 1.509 (4) |
C6—C18A | 1.622 (6) | C25—C26A | 1.549 (6) |
C7—H7 | 0.9500 | C25—C27A | 1.502 (6) |
C7—C8 | 1.417 (2) | C25—C28A | 1.538 (6) |
C8—C9 | 1.200 (2) | C18—H18A | 0.9900 |
C9—C19 | 1.431 (2) | C18—H18B | 0.9900 |
C10—C11 | 1.398 (2) | C26—H26A | 0.9800 |
C10—C15 | 1.392 (3) | C26—H26B | 0.9800 |
C11—H11 | 0.9500 | C26—H26C | 0.9800 |
C11—C12 | 1.374 (3) | C27—H27A | 0.9800 |
C12—H12 | 0.9500 | C27—H27B | 0.9800 |
C12—C13 | 1.378 (3) | C27—H27C | 0.9800 |
C13—H13 | 0.9500 | C28—H28A | 0.9800 |
C13—C14 | 1.378 (3) | C28—H28B | 0.9800 |
C14—H14 | 0.9500 | C28—H28C | 0.9800 |
C14—C15 | 1.378 (3) | C18A—H18C | 0.9900 |
C15—H15 | 0.9500 | C18A—H18D | 0.9900 |
C16—H16A | 0.9900 | C26A—H26D | 0.9800 |
C16—H16B | 0.9900 | C26A—H26E | 0.9800 |
C16—C17 | 1.475 (2) | C26A—H26F | 0.9800 |
C17—C25 | 1.539 (3) | C27A—H27D | 0.9800 |
C17—C18 | 1.455 (3) | C27A—H27E | 0.9800 |
C17—C18A | 1.355 (6) | C27A—H27F | 0.9800 |
C19—C20 | 1.388 (3) | C28A—H28D | 0.9800 |
C19—C24 | 1.394 (3) | C28A—H28E | 0.9800 |
C20—H20 | 0.9500 | C28A—H28F | 0.9800 |
C2—C1—C10 | 179.1 (2) | C24—C23—H23 | 119.8 |
C1—C2—C3 | 178.31 (19) | C19—C24—H24 | 120.0 |
C2—C3—H3 | 117.5 | C23—C24—C19 | 120.07 (18) |
C4—C3—C2 | 124.98 (17) | C23—C24—H24 | 120.0 |
C4—C3—H3 | 117.5 | C17—C25—C27 | 110.5 (2) |
C3—C4—C5 | 117.67 (16) | C17—C25—C26A | 116.5 (3) |
C3—C4—C16 | 121.00 (16) | C26—C25—C17 | 105.3 (2) |
C5—C4—C16 | 121.31 (15) | C26—C25—C27 | 108.7 (3) |
O1—C5—C4 | 121.52 (15) | C28—C25—C17 | 112.2 (2) |
O1—C5—C6 | 120.67 (16) | C28—C25—C26 | 110.6 (3) |
C4—C5—C6 | 117.81 (15) | C28—C25—C27 | 109.5 (3) |
C5—C6—C18 | 115.94 (18) | C27A—C25—C17 | 116.3 (3) |
C5—C6—C18A | 115.0 (2) | C27A—C25—C26A | 107.5 (4) |
C7—C6—C5 | 119.54 (17) | C27A—C25—C28A | 109.1 (4) |
C7—C6—C18 | 123.61 (18) | C28A—C25—C17 | 101.3 (3) |
C7—C6—C18A | 118.1 (2) | C28A—C25—C26A | 105.2 (4) |
C6—C7—H7 | 117.3 | C6—C18—H18A | 108.7 |
C6—C7—C8 | 125.48 (17) | C6—C18—H18B | 108.7 |
C8—C7—H7 | 117.3 | C17—C18—C6 | 114.0 (2) |
C9—C8—C7 | 178.87 (19) | C17—C18—H18A | 108.7 |
C8—C9—C19 | 178.5 (2) | C17—C18—H18B | 108.7 |
C11—C10—C1 | 120.08 (17) | H18A—C18—H18B | 107.6 |
C15—C10—C1 | 121.23 (16) | C25—C26—H26A | 109.5 |
C15—C10—C11 | 118.69 (16) | C25—C26—H26B | 109.5 |
C10—C11—H11 | 119.7 | C25—C26—H26C | 109.5 |
C12—C11—C10 | 120.50 (18) | H26A—C26—H26B | 109.5 |
C12—C11—H11 | 119.7 | H26A—C26—H26C | 109.5 |
C11—C12—H12 | 119.9 | H26B—C26—H26C | 109.5 |
C11—C12—C13 | 120.23 (18) | C25—C27—H27A | 109.5 |
C13—C12—H12 | 119.9 | C25—C27—H27B | 109.5 |
C12—C13—H13 | 120.1 | C25—C27—H27C | 109.5 |
C14—C13—C12 | 119.85 (19) | H27A—C27—H27B | 109.5 |
C14—C13—H13 | 120.1 | H27A—C27—H27C | 109.5 |
C13—C14—H14 | 119.8 | H27B—C27—H27C | 109.5 |
C15—C14—C13 | 120.49 (19) | C25—C28—H28A | 109.5 |
C15—C14—H14 | 119.8 | C25—C28—H28B | 109.5 |
C10—C15—H15 | 119.9 | C25—C28—H28C | 109.5 |
C14—C15—C10 | 120.22 (17) | H28A—C28—H28B | 109.5 |
C14—C15—H15 | 119.9 | H28A—C28—H28C | 109.5 |
C4—C16—H16A | 108.1 | H28B—C28—H28C | 109.5 |
C4—C16—H16B | 108.1 | C6—C18A—H18C | 109.0 |
H16A—C16—H16B | 107.3 | C6—C18A—H18D | 109.0 |
C17—C16—C4 | 116.69 (16) | C17—C18A—C6 | 113.1 (4) |
C17—C16—H16A | 108.1 | C17—C18A—H18C | 109.0 |
C17—C16—H16B | 108.1 | C17—C18A—H18D | 109.0 |
C16—C17—C25 | 116.29 (16) | H18C—C18A—H18D | 107.8 |
C18—C17—C16 | 115.98 (19) | C25—C26A—H26D | 109.5 |
C18—C17—C25 | 119.12 (18) | C25—C26A—H26E | 109.5 |
C18A—C17—C16 | 122.8 (3) | C25—C26A—H26F | 109.5 |
C18A—C17—C25 | 119.2 (3) | H26D—C26A—H26E | 109.5 |
C20—C19—C9 | 119.90 (17) | H26D—C26A—H26F | 109.5 |
C20—C19—C24 | 119.25 (16) | H26E—C26A—H26F | 109.5 |
C24—C19—C9 | 120.82 (16) | C25—C27A—H27D | 109.5 |
C19—C20—H20 | 120.1 | C25—C27A—H27E | 109.5 |
C21—C20—C19 | 119.88 (19) | C25—C27A—H27F | 109.5 |
C21—C20—H20 | 120.1 | H27D—C27A—H27E | 109.5 |
C20—C21—H21 | 119.7 | H27D—C27A—H27F | 109.5 |
C22—C21—C20 | 120.5 (2) | H27E—C27A—H27F | 109.5 |
C22—C21—H21 | 119.7 | C25—C28A—H28D | 109.5 |
C21—C22—H22 | 120.0 | C25—C28A—H28E | 109.5 |
C23—C22—C21 | 119.93 (19) | C25—C28A—H28F | 109.5 |
C23—C22—H22 | 120.0 | H28D—C28A—H28E | 109.5 |
C22—C23—H23 | 119.8 | H28D—C28A—H28F | 109.5 |
C22—C23—C24 | 120.33 (19) | H28E—C28A—H28F | 109.5 |
O1—C5—C6—C7 | −7.9 (3) | C16—C17—C25—C27 | 160.2 (3) |
O1—C5—C6—C18 | 161.6 (2) | C16—C17—C25—C28 | 37.7 (3) |
O1—C5—C6—C18A | −157.3 (3) | C16—C17—C25—C26A | −21.1 (5) |
C1—C10—C11—C12 | −178.50 (17) | C16—C17—C25—C27A | −149.5 (4) |
C1—C10—C15—C14 | 179.11 (18) | C16—C17—C25—C28A | 92.4 (3) |
C2—C3—C4—C5 | −178.96 (17) | C16—C17—C18—C6 | −49.9 (4) |
C2—C3—C4—C16 | −0.2 (3) | C16—C17—C18A—C6 | 39.1 (6) |
C3—C4—C5—O1 | −2.1 (3) | C19—C20—C21—C22 | −1.0 (3) |
C3—C4—C5—C6 | 178.41 (18) | C20—C19—C24—C23 | 0.5 (3) |
C3—C4—C16—C17 | 176.5 (2) | C20—C21—C22—C23 | 0.8 (4) |
C4—C5—C6—C7 | 171.65 (17) | C21—C22—C23—C24 | 0.1 (3) |
C4—C5—C6—C18 | −18.9 (3) | C22—C23—C24—C19 | −0.7 (3) |
C4—C5—C6—C18A | 22.2 (3) | C24—C19—C20—C21 | 0.4 (3) |
C4—C16—C17—C25 | 177.85 (19) | C25—C17—C18—C6 | 163.5 (2) |
C4—C16—C17—C18 | 30.2 (3) | C25—C17—C18A—C6 | −156.3 (3) |
C4—C16—C17—C18A | −17.1 (5) | C18—C6—C7—C8 | 13.0 (3) |
C5—C4—C16—C17 | −4.8 (3) | C18—C6—C18A—C17 | 59.2 (4) |
C5—C6—C7—C8 | −178.37 (17) | C18—C17—C25—C26 | 64.0 (3) |
C5—C6—C18—C17 | 44.0 (3) | C18—C17—C25—C27 | −53.2 (4) |
C5—C6—C18A—C17 | −41.4 (5) | C18—C17—C25—C28 | −175.7 (3) |
C7—C6—C18—C17 | −147.0 (2) | C18—C17—C25—C26A | 125.4 (4) |
C7—C6—C18A—C17 | 168.7 (3) | C18—C17—C25—C27A | −3.0 (5) |
C9—C19—C20—C21 | −177.85 (19) | C18—C17—C25—C28A | −121.1 (3) |
C9—C19—C24—C23 | 178.68 (17) | C18—C17—C18A—C6 | −54.2 (4) |
C10—C11—C12—C13 | −0.4 (3) | C18A—C6—C7—C8 | −29.9 (4) |
C11—C10—C15—C14 | −0.4 (3) | C18A—C6—C18—C17 | −53.7 (4) |
C11—C12—C13—C14 | −0.9 (3) | C18A—C17—C25—C26 | 111.9 (4) |
C12—C13—C14—C15 | 1.5 (3) | C18A—C17—C25—C27 | −5.4 (5) |
C13—C14—C15—C10 | −0.9 (3) | C18A—C17—C25—C28 | −127.8 (4) |
C15—C10—C11—C12 | 1.0 (3) | C18A—C17—C25—C26A | 173.3 (5) |
C16—C4—C5—O1 | 179.17 (18) | C18A—C17—C25—C27A | 44.9 (6) |
C16—C4—C5—C6 | −0.3 (3) | C18A—C17—C25—C28A | −73.2 (5) |
C16—C17—C25—C26 | −82.6 (3) | C18A—C17—C18—C6 | 61.1 (4) |
C30H30O | F(000) = 872 |
Mr = 406.54 | Dx = 1.090 Mg m−3 |
Monoclinic, Cc | Synchrotron radiation, λ = 0.96990 Å |
a = 6.4010 (13) Å | Cell parameters from 3567 reflections |
b = 21.350 (4) Å | θ = 3.1–38.7° |
c = 18.190 (4) Å | µ = 0.14 mm−1 |
β = 94.83 (3)° | T = 120 K |
V = 2477.1 (9) Å3 | Needle, yellow |
Z = 4 | 0.5 × 0.02 × 0.02 mm |
Mar CCD diffractometer | 2588 independent reflections |
Radiation source: fine-focus sealed tube | 1287 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.238 |
phi–scan | θmax = 38.4°, θmin = 2.6° |
Absorption correction: multi-scan (SCALA; Evans, 2006) | h = −7→8 |
Tmin = 0.899, Tmax = 0.902 | k = −26→25 |
10989 measured reflections | l = −21→22 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.140 | H-atom parameters constrained |
wR(F2) = 0.339 | w = 1/[σ2(Fo2) + (0.010P)2 + 3.2P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2588 reflections | Δρmax = 0.37 e Å−3 |
279 parameters | Δρmin = −0.32 e Å−3 |
23 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.146 (19) |
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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.6468 (12) | 0.5022 (3) | 0.3726 (4) | 0.0721 (19) | |
C20 | 1.2839 (15) | 0.7564 (4) | 0.3294 (5) | 0.057 (2) | |
C3 | 0.8961 (16) | 0.6089 (5) | 0.3589 (5) | 0.066 (3) | |
H3 | 0.8949 | 0.5766 | 0.3229 | 0.079* | |
C1 | 1.1471 (16) | 0.7050 (5) | 0.3427 (5) | 0.063 (3) | |
C16 | −0.5004 (15) | 0.4357 (4) | 0.6742 (5) | 0.058 (2) | |
C5 | 0.6225 (14) | 0.5465 (4) | 0.4149 (4) | 0.058 (2) | |
C7 | 0.4256 (16) | 0.6031 (4) | 0.5156 (5) | 0.064 (3) | |
H7AA | 0.4790 | 0.5911 | 0.5663 | 0.076* | 0.50 |
H7AB | 0.2740 | 0.6120 | 0.5163 | 0.076* | 0.50 |
H7BC | 0.2864 | 0.6218 | 0.5016 | 0.076* | 0.50 |
H7BD | 0.4219 | 0.5866 | 0.5664 | 0.076* | 0.50 |
C2 | 1.0343 (15) | 0.6607 (5) | 0.3528 (5) | 0.059 (2) | |
C13 | −0.1701 (14) | 0.4651 (4) | 0.5893 (5) | 0.056 (2) | |
C14 | −0.2113 (16) | 0.5039 (4) | 0.6478 (5) | 0.061 (2) | |
H14 | −0.1280 | 0.5401 | 0.6587 | 0.073* | |
C25 | 1.4813 (15) | 0.7444 (4) | 0.2978 (5) | 0.059 (3) | |
H25 | 1.5184 | 0.7029 | 0.2853 | 0.071* | |
C6 | 0.4518 (15) | 0.5487 (4) | 0.4658 (4) | 0.054 (2) | |
C18 | −0.2899 (17) | 0.4120 (4) | 0.5732 (6) | 0.070 (3) | |
H18 | −0.2594 | 0.3854 | 0.5337 | 0.084* | |
C15 | −0.3830 (16) | 0.4886 (4) | 0.6922 (5) | 0.062 (3) | |
H15 | −0.4135 | 0.5144 | 0.7325 | 0.074* | |
C4 | 0.7618 (15) | 0.6034 (4) | 0.4157 (5) | 0.059 (2) | |
C12 | 0.0043 (17) | 0.4797 (4) | 0.5464 (6) | 0.066 (3) | |
C10 | 0.3228 (17) | 0.4973 (5) | 0.4630 (5) | 0.070 (3) | |
H10 | 0.3511 | 0.4648 | 0.4295 | 0.084* | |
C17 | −0.4578 (18) | 0.3979 (5) | 0.6160 (6) | 0.069 (3) | |
H17 | −0.5421 | 0.3620 | 0.6046 | 0.083* | |
C24 | 1.6161 (17) | 0.7943 (4) | 0.2859 (6) | 0.070 (3) | |
H24 | 1.7490 | 0.7859 | 0.2684 | 0.084* | |
C11 | 0.1459 (18) | 0.4886 (4) | 0.5073 (6) | 0.066 (3) | |
C21 | 1.237 (2) | 0.8178 (5) | 0.3458 (6) | 0.075 (3) | |
H21 | 1.1089 | 0.8267 | 0.3668 | 0.090* | |
C22 | 1.372 (2) | 0.8671 (5) | 0.3321 (7) | 0.088 (4) | |
H22 | 1.3374 | 0.9087 | 0.3450 | 0.105* | |
C27 | 0.5296 (17) | 0.7143 (5) | 0.5598 (6) | 0.078 (3) | |
C19 | −0.6853 (16) | 0.4200 (5) | 0.7179 (7) | 0.076 (3) | |
H19A | −0.6420 | 0.4225 | 0.7708 | 0.114* | |
H19B | −0.7343 | 0.3775 | 0.7056 | 0.114* | |
H19C | −0.7990 | 0.4499 | 0.7055 | 0.114* | |
C23 | 1.560 (2) | 0.8549 (4) | 0.2990 (7) | 0.086 (4) | |
C8 | 0.541 (3) | 0.6655 (7) | 0.4940 (12) | 0.061 (4)* | 0.50 |
H8 | 0.4766 | 0.6831 | 0.4464 | 0.073* | 0.50 |
C26 | 1.708 (2) | 0.9096 (5) | 0.2783 (7) | 0.093 (4) | |
H26A | 1.8464 | 0.9043 | 0.3051 | 0.139* | |
H26B | 1.6481 | 0.9498 | 0.2918 | 0.139* | |
H26C | 1.7224 | 0.9089 | 0.2251 | 0.139* | |
C9 | 0.767 (3) | 0.6405 (9) | 0.4860 (12) | 0.067 (4)* | 0.50 |
H9A | 0.8659 | 0.6759 | 0.4843 | 0.081* | 0.50 |
H9B | 0.8130 | 0.6136 | 0.5286 | 0.081* | 0.50 |
C29 | 0.316 (4) | 0.7380 (11) | 0.5528 (15) | 0.078 (4)* | 0.50 |
H29A | 0.2672 | 0.7415 | 0.5005 | 0.118* | 0.50 |
H29B | 0.3124 | 0.7793 | 0.5761 | 0.118* | 0.50 |
H29C | 0.2250 | 0.7091 | 0.5771 | 0.118* | 0.50 |
C28 | 0.642 (6) | 0.7750 (16) | 0.530 (2) | 0.098 (5)* | 0.50 |
H28A | 0.7925 | 0.7730 | 0.5440 | 0.147* | 0.50 |
H28B | 0.5829 | 0.8127 | 0.5507 | 0.147* | 0.50 |
H28C | 0.6181 | 0.7765 | 0.4757 | 0.147* | 0.50 |
C30 | 0.606 (5) | 0.6894 (13) | 0.6385 (16) | 0.099 (6)* | 0.50 |
H30A | 0.5991 | 0.7233 | 0.6745 | 0.148* | 0.50 |
H30B | 0.7508 | 0.6746 | 0.6386 | 0.148* | 0.50 |
H30C | 0.5156 | 0.6548 | 0.6516 | 0.148* | 0.50 |
C9A | 0.728 (4) | 0.6644 (10) | 0.4619 (13) | 0.067 (4)* | 0.50 |
H9AA | 0.8636 | 0.6783 | 0.4865 | 0.081* | 0.50 |
H9AB | 0.6732 | 0.6983 | 0.4284 | 0.081* | 0.50 |
C8A | 0.578 (3) | 0.6530 (8) | 0.5182 (11) | 0.061 (4)* | 0.50 |
H8A | 0.6803 | 0.6347 | 0.5570 | 0.073* | 0.50 |
C30A | 0.677 (3) | 0.7102 (12) | 0.6269 (12) | 0.099 (6)* | 0.50 |
H30D | 0.6979 | 0.6662 | 0.6409 | 0.148* | 0.50 |
H30E | 0.6193 | 0.7330 | 0.6673 | 0.148* | 0.50 |
H30F | 0.8120 | 0.7287 | 0.6169 | 0.148* | 0.50 |
C29A | 0.299 (2) | 0.7231 (11) | 0.5767 (13) | 0.078 (4)* | 0.50 |
H29D | 0.2096 | 0.7249 | 0.5303 | 0.118* | 0.50 |
H29E | 0.2854 | 0.7621 | 0.6041 | 0.118* | 0.50 |
H29F | 0.2563 | 0.6877 | 0.6063 | 0.118* | 0.50 |
C28A | 0.589 (4) | 0.7761 (13) | 0.5185 (16) | 0.098 (5)* | 0.50 |
H28D | 0.7254 | 0.7708 | 0.4989 | 0.147* | 0.50 |
H28E | 0.5949 | 0.8113 | 0.5532 | 0.147* | 0.50 |
H28F | 0.4819 | 0.7845 | 0.4778 | 0.147* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.089 (5) | 0.071 (4) | 0.059 (4) | 0.012 (3) | 0.023 (3) | −0.013 (3) |
C20 | 0.065 (6) | 0.058 (5) | 0.045 (5) | 0.012 (5) | −0.011 (5) | −0.011 (4) |
C3 | 0.075 (7) | 0.078 (6) | 0.044 (5) | 0.011 (5) | 0.005 (5) | 0.004 (4) |
C1 | 0.067 (7) | 0.077 (6) | 0.040 (5) | 0.025 (6) | −0.016 (5) | −0.002 (4) |
C16 | 0.063 (6) | 0.056 (4) | 0.054 (5) | −0.002 (5) | −0.002 (4) | 0.009 (4) |
C5 | 0.064 (6) | 0.072 (6) | 0.039 (4) | 0.008 (5) | 0.008 (4) | −0.011 (4) |
C7 | 0.081 (7) | 0.057 (5) | 0.052 (5) | 0.002 (5) | 0.002 (5) | −0.001 (4) |
C2 | 0.059 (6) | 0.070 (6) | 0.046 (5) | 0.018 (5) | −0.003 (4) | −0.003 (4) |
C13 | 0.060 (6) | 0.057 (4) | 0.050 (5) | −0.003 (4) | −0.003 (4) | 0.008 (4) |
C14 | 0.067 (6) | 0.061 (5) | 0.053 (5) | −0.003 (5) | 0.002 (5) | −0.001 (4) |
C25 | 0.074 (7) | 0.057 (5) | 0.043 (5) | 0.000 (5) | −0.018 (5) | 0.000 (4) |
C6 | 0.068 (6) | 0.055 (5) | 0.039 (4) | 0.021 (4) | 0.011 (4) | 0.000 (3) |
C18 | 0.080 (7) | 0.048 (5) | 0.082 (7) | −0.011 (5) | 0.007 (6) | 0.000 (4) |
C15 | 0.075 (7) | 0.051 (5) | 0.060 (5) | −0.009 (4) | 0.009 (5) | 0.012 (4) |
C4 | 0.065 (6) | 0.063 (5) | 0.051 (5) | 0.014 (5) | 0.009 (5) | −0.003 (4) |
C12 | 0.067 (7) | 0.066 (6) | 0.065 (6) | 0.000 (5) | 0.004 (6) | 0.009 (5) |
C10 | 0.085 (8) | 0.074 (6) | 0.049 (5) | 0.002 (6) | −0.002 (5) | −0.003 (4) |
C17 | 0.079 (7) | 0.060 (5) | 0.066 (6) | −0.001 (5) | −0.006 (5) | −0.001 (5) |
C24 | 0.065 (7) | 0.057 (5) | 0.085 (7) | −0.009 (5) | −0.007 (5) | 0.002 (5) |
C11 | 0.074 (7) | 0.068 (6) | 0.055 (6) | −0.001 (5) | −0.006 (6) | 0.006 (5) |
C21 | 0.102 (8) | 0.060 (5) | 0.060 (6) | 0.028 (6) | −0.015 (6) | −0.006 (4) |
C22 | 0.111 (10) | 0.060 (6) | 0.086 (8) | 0.031 (7) | −0.033 (8) | −0.024 (5) |
C27 | 0.072 (5) | 0.092 (5) | 0.072 (5) | −0.019 (4) | 0.014 (4) | −0.021 (4) |
C19 | 0.060 (6) | 0.079 (6) | 0.088 (7) | −0.002 (5) | 0.005 (5) | 0.038 (6) |
C23 | 0.111 (10) | 0.044 (5) | 0.091 (8) | −0.008 (6) | −0.056 (8) | 0.004 (5) |
C26 | 0.091 (6) | 0.083 (5) | 0.101 (6) | −0.009 (5) | −0.012 (5) | 0.005 (5) |
O1—C5 | 1.238 (10) | C22—C23 | 1.416 (19) |
C20—C1 | 1.439 (15) | C27—C8 | 1.59 (2) |
C20—C25 | 1.454 (14) | C27—C29 | 1.45 (3) |
C20—C21 | 1.383 (12) | C27—C28 | 1.60 (3) |
C3—H3 | 0.9500 | C27—C30 | 1.57 (3) |
C3—C2 | 1.426 (16) | C27—C8A | 1.56 (2) |
C3—C4 | 1.402 (13) | C27—C30A | 1.482 (16) |
C1—C2 | 1.213 (14) | C27—C29A | 1.543 (16) |
C16—C15 | 1.380 (13) | C27—C28A | 1.579 (17) |
C16—C17 | 1.377 (14) | C19—H19A | 0.9800 |
C16—C19 | 1.517 (14) | C19—H19B | 0.9800 |
C5—C6 | 1.491 (12) | C19—H19C | 0.9800 |
C5—C4 | 1.505 (13) | C23—C26 | 1.569 (17) |
C7—H7AA | 0.9900 | C8—H8 | 1.0000 |
C7—H7AB | 0.9900 | C8—C9 | 1.559 (18) |
C7—H7BC | 0.9900 | C26—H26A | 0.9800 |
C7—H7BD | 0.9900 | C26—H26B | 0.9800 |
C7—C6 | 1.491 (11) | C26—H26C | 0.9800 |
C7—C8 | 1.589 (15) | C9—H9A | 0.9900 |
C7—C8A | 1.446 (15) | C9—H9B | 0.9900 |
C13—C14 | 1.390 (13) | C29—H29A | 0.9800 |
C13—C18 | 1.387 (12) | C29—H29B | 0.9800 |
C13—C12 | 1.449 (14) | C29—H29C | 0.9800 |
C14—H14 | 0.9500 | C28—H28A | 0.9800 |
C14—C15 | 1.454 (14) | C28—H28B | 0.9800 |
C25—H25 | 0.9500 | C28—H28C | 0.9800 |
C25—C24 | 1.399 (13) | C30—H30A | 0.9800 |
C6—C10 | 1.373 (13) | C30—H30B | 0.9800 |
C18—H18 | 0.9500 | C30—H30C | 0.9800 |
C18—C17 | 1.412 (15) | C9A—H9AA | 0.9900 |
C15—H15 | 0.9500 | C9A—H9AB | 0.9900 |
C4—C9 | 1.50 (2) | C9A—C8A | 1.48 (3) |
C4—C9A | 1.58 (2) | C8A—H8A | 1.0000 |
C12—C11 | 1.213 (15) | C30A—H30D | 0.9800 |
C10—H10 | 0.9500 | C30A—H30E | 0.9800 |
C10—C11 | 1.457 (16) | C30A—H30F | 0.9800 |
C17—H17 | 0.9500 | C29A—H29D | 0.9800 |
C24—H24 | 0.9500 | C29A—H29E | 0.9800 |
C24—C23 | 1.370 (14) | C29A—H29F | 0.9800 |
C21—H21 | 0.9500 | C28A—H28D | 0.9800 |
C21—C22 | 1.398 (19) | C28A—H28E | 0.9800 |
C22—H22 | 0.9500 | C28A—H28F | 0.9800 |
C1—C20—C25 | 119.5 (7) | C30—C27—C28 | 118.3 (19) |
C21—C20—C1 | 122.7 (10) | C30—C27—C28A | 130.5 (17) |
C21—C20—C25 | 117.8 (10) | C8A—C27—C8 | 20.1 (10) |
C2—C3—H3 | 118.5 | C8A—C27—C28 | 113.6 (16) |
C4—C3—H3 | 118.5 | C8A—C27—C30 | 95.7 (14) |
C4—C3—C2 | 123.0 (9) | C8A—C27—C28A | 113.9 (17) |
C2—C1—C20 | 178.4 (10) | C30A—C27—C8 | 121.0 (15) |
C15—C16—C19 | 119.3 (9) | C30A—C27—C28 | 93.3 (19) |
C17—C16—C15 | 121.5 (9) | C30A—C27—C30 | 25.7 (14) |
C17—C16—C19 | 119.1 (9) | C30A—C27—C8A | 102.2 (15) |
O1—C5—C6 | 123.1 (9) | C30A—C27—C29A | 113.4 (14) |
O1—C5—C4 | 121.1 (8) | C30A—C27—C28A | 106.2 (13) |
C6—C5—C4 | 115.7 (7) | C29A—C27—C8 | 109.5 (13) |
H7AA—C7—H7AB | 107.5 | C29A—C27—C28 | 115.7 (19) |
H7AA—C7—H7BC | 125.3 | C29A—C27—C30 | 95.1 (15) |
H7AA—C7—H7BD | 22.0 | C29A—C27—C8A | 115.7 (13) |
H7AB—C7—H7BC | 20.5 | C29A—C27—C28A | 105.3 (13) |
H7AB—C7—H7BD | 87.6 | C28A—C27—C8 | 99.3 (16) |
H7BC—C7—H7BD | 107.0 | C28A—C27—C28 | 14 (2) |
C6—C7—H7AA | 108.5 | C16—C19—H19A | 109.5 |
C6—C7—H7AB | 108.5 | C16—C19—H19B | 109.5 |
C6—C7—H7BC | 107.6 | C16—C19—H19C | 109.5 |
C6—C7—H7BD | 107.6 | H19A—C19—H19B | 109.5 |
C6—C7—C8 | 115.1 (10) | H19A—C19—H19C | 109.5 |
C8—C7—H7AA | 108.5 | H19B—C19—H19C | 109.5 |
C8—C7—H7AB | 108.5 | C24—C23—C22 | 119.5 (11) |
C8—C7—H7BC | 91.4 | C24—C23—C26 | 119.3 (14) |
C8—C7—H7BD | 125.3 | C22—C23—C26 | 121.2 (10) |
C8A—C7—H7AA | 89.0 | C7—C8—C27 | 108.1 (12) |
C8A—C7—H7AB | 121.3 | C7—C8—H8 | 111.4 |
C8A—C7—H7BC | 107.6 | C27—C8—H8 | 111.4 |
C8A—C7—H7BD | 107.6 | C9—C8—C7 | 100.9 (13) |
C8A—C7—C6 | 118.9 (11) | C9—C8—C27 | 113.3 (14) |
C8A—C7—C8 | 20.3 (11) | C9—C8—H8 | 111.4 |
C1—C2—C3 | 175.7 (9) | C23—C26—H26A | 109.5 |
C14—C13—C12 | 119.3 (8) | C23—C26—H26B | 109.5 |
C18—C13—C14 | 120.8 (9) | C23—C26—H26C | 109.5 |
C18—C13—C12 | 119.9 (9) | H26A—C26—H26B | 109.5 |
C13—C14—H14 | 120.3 | H26A—C26—H26C | 109.5 |
C13—C14—C15 | 119.5 (8) | H26B—C26—H26C | 109.5 |
C15—C14—H14 | 120.3 | C4—C9—C8 | 107.9 (15) |
C20—C25—H25 | 120.2 | C4—C9—H9A | 110.1 |
C24—C25—C20 | 119.6 (8) | C4—C9—H9B | 110.1 |
C24—C25—H25 | 120.2 | C8—C9—H9A | 110.1 |
C7—C6—C5 | 121.8 (8) | C8—C9—H9B | 110.1 |
C10—C6—C5 | 114.9 (8) | H9A—C9—H9B | 108.4 |
C10—C6—C7 | 123.2 (8) | C27—C29—H29A | 109.5 |
C13—C18—H18 | 120.3 | C27—C29—H29B | 109.5 |
C13—C18—C17 | 119.4 (10) | C27—C29—H29C | 109.5 |
C17—C18—H18 | 120.3 | C27—C28—H28A | 109.5 |
C16—C15—C14 | 118.3 (9) | C27—C28—H28B | 109.5 |
C16—C15—H15 | 120.8 | C27—C28—H28C | 109.5 |
C14—C15—H15 | 120.8 | C27—C30—H30A | 109.5 |
C3—C4—C5 | 117.4 (8) | C27—C30—H30B | 109.5 |
C3—C4—C9 | 127.7 (11) | C27—C30—H30C | 109.5 |
C3—C4—C9A | 116.4 (10) | C4—C9A—H9AA | 109.4 |
C5—C4—C9A | 124.2 (10) | C4—C9A—H9AB | 109.4 |
C9—C4—C5 | 113.8 (10) | H9AA—C9A—H9AB | 108.0 |
C9—C4—C9A | 26.3 (9) | C8A—C9A—C4 | 111.1 (15) |
C11—C12—C13 | 175.6 (11) | C8A—C9A—H9AA | 109.4 |
C6—C10—H10 | 117.5 | C8A—C9A—H9AB | 109.4 |
C6—C10—C11 | 125.0 (9) | C7—C8A—C27 | 118.2 (14) |
C11—C10—H10 | 117.5 | C7—C8A—C9A | 125.1 (16) |
C16—C17—C18 | 120.6 (9) | C7—C8A—H8A | 97.6 |
C16—C17—H17 | 119.7 | C27—C8A—H8A | 97.6 |
C18—C17—H17 | 119.7 | C9A—C8A—C27 | 111.5 (13) |
C25—C24—H24 | 119.4 | C9A—C8A—H8A | 97.6 |
C23—C24—C25 | 121.3 (12) | C27—C30A—H30D | 109.5 |
C23—C24—H24 | 119.4 | C27—C30A—H30E | 109.5 |
C12—C11—C10 | 177.1 (10) | C27—C30A—H30F | 109.5 |
C20—C21—H21 | 119.2 | H30D—C30A—H30E | 109.5 |
C20—C21—C22 | 121.6 (12) | H30D—C30A—H30F | 109.5 |
C22—C21—H21 | 119.2 | H30E—C30A—H30F | 109.5 |
C21—C22—H22 | 120.0 | C27—C29A—H29D | 109.5 |
C21—C22—C23 | 120.0 (9) | C27—C29A—H29E | 109.5 |
C23—C22—H22 | 120.0 | C27—C29A—H29F | 109.5 |
C8—C27—C28 | 102.9 (16) | H29D—C29A—H29E | 109.5 |
C29—C27—C8 | 105.3 (14) | H29D—C29A—H29F | 109.5 |
C29—C27—C28 | 97.7 (18) | H29E—C29A—H29F | 109.5 |
C29—C27—C30 | 114.6 (17) | C27—C28A—H28D | 109.5 |
C29—C27—C8A | 118.4 (15) | C27—C28A—H28E | 109.5 |
C29—C27—C30A | 128.5 (17) | C27—C28A—H28F | 109.5 |
C29—C27—C29A | 21.1 (13) | H28D—C28A—H28E | 109.5 |
C29—C27—C28A | 85.9 (15) | H28D—C28A—H28F | 109.5 |
C30—C27—C8 | 115.8 (14) | H28E—C28A—H28F | 109.5 |
C20H16O2 | Dx = 1.309 Mg m−3 |
Mr = 288.33 | Synchrotron radiation, λ = 0.9699 Å |
Orthorhombic, Pca21 | Cell parameters from 7860 reflections |
a = 9.5892 (19) Å | θ = 4–37° |
b = 10.145 (2) Å | µ = 0.19 mm−1 |
c = 30.080 (6) Å | T = 100 K |
V = 2926.2 (10) Å3 | Needle, yellow |
Z = 8 | 0.4 × 0.03 × 0.02 mm |
F(000) = 1216 |
Mar CCD diffractometer | 3732 reflections with I > 2σ(I) |
phi scan | Rint = 0.091 |
Absorption correction: multi-scan (SCALA; Evans, 2006) | θmax = 38.4°, θmin = 3.3° |
Tmin = 0.945, Tmax = 0.999 | h = −12→12 |
15016 measured reflections | k = −12→12 |
5675 independent reflections | l = −37→37 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.095 | w = 1/[σ2(Fo2) + (0.010P)2 + 9.P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.250 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 1.08 e Å−3 |
5675 reflections | Δρmin = −0.51 e Å−3 |
397 parameters | Absolute structure: Flack x determined using 1267 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
1 restraint | Absolute structure parameter: 0.3 (8) |
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 | 0.3773 (6) | 1.1962 (6) | 0.60435 (19) | 0.0235 (13) | |
O2 | 0.6231 (7) | 1.1074 (5) | 0.46728 (17) | 0.0321 (14) | |
C1 | 0.4773 (8) | 1.0691 (8) | 0.5291 (3) | 0.0256 (17) | |
H1 | 0.4943 | 1.1596 | 0.5352 | 0.031* | |
C2 | 0.4037 (10) | 1.0017 (6) | 0.5582 (3) | 0.016 (2) | |
C3 | 0.3486 (9) | 1.0772 (8) | 0.5991 (3) | 0.0280 (18) | |
C4 | 0.2561 (10) | 1.0075 (7) | 0.6306 (3) | 0.0170 (19) | |
C5 | 0.1852 (9) | 1.0857 (9) | 0.6609 (3) | 0.0286 (18) | |
H5 | 0.2042 | 1.1776 | 0.6597 | 0.034* | |
C6 | 0.0870 (10) | 1.0444 (10) | 0.6937 (3) | 0.0324 (19) | |
C7 | −0.0009 (10) | 1.0200 (9) | 0.7211 (3) | 0.024 (2) | |
C8 | 0.3732 (9) | 0.8555 (8) | 0.5571 (3) | 0.0299 (19) | |
H8A | 0.4492 | 0.8096 | 0.5410 | 0.036* | |
H8B | 0.2854 | 0.8402 | 0.5406 | 0.036* | |
C9 | 0.3599 (8) | 0.7976 (9) | 0.6040 (3) | 0.0176 (17) | |
H9A | 0.4459 | 0.8154 | 0.6212 | 0.021* | |
H9B | 0.3469 | 0.7009 | 0.6022 | 0.021* | |
C10 | 0.2312 (9) | 0.8624 (9) | 0.6278 (3) | 0.0293 (18) | |
H10A | 0.1451 | 0.8446 | 0.6106 | 0.035* | |
H10B | 0.2199 | 0.8249 | 0.6579 | 0.035* | |
C11 | 0.5339 (9) | 1.0156 (8) | 0.4886 (2) | 0.0153 (17) | |
C12 | 0.5244 (12) | 0.9110 (8) | 0.4620 (3) | 0.039 (2) | |
H12 | 0.4712 | 0.8339 | 0.4676 | 0.047* | |
C13 | 0.6084 (13) | 0.9348 (11) | 0.4233 (3) | 0.046 (3) | |
H13 | 0.6196 | 0.8769 | 0.3987 | 0.056* | |
C14 | 0.6659 (9) | 1.0491 (10) | 0.4280 (3) | 0.028 (2) | |
H14 | 0.7287 | 1.0877 | 0.4073 | 0.034* | |
C15 | −0.1028 (9) | 1.0083 (7) | 0.7571 (3) | 0.018 (2) | |
C16 | −0.1557 (9) | 0.8874 (9) | 0.7712 (3) | 0.023 (2) | |
H16 | −0.1214 | 0.8081 | 0.7584 | 0.028* | |
C17 | −0.2606 (9) | 0.8816 (9) | 0.8046 (3) | 0.0231 (19) | |
H17 | −0.2960 | 0.7988 | 0.8141 | 0.028* | |
C18 | −0.3108 (10) | 0.9968 (8) | 0.8232 (3) | 0.023 (2) | |
H18 | −0.3808 | 0.9928 | 0.8455 | 0.027* | |
C19 | −0.2593 (9) | 1.1191 (9) | 0.8096 (2) | 0.0221 (19) | |
H19 | −0.2939 | 1.1982 | 0.8224 | 0.027* | |
C20 | −0.1565 (9) | 1.1235 (10) | 0.7768 (3) | 0.0219 (19) | |
H20 | −0.1215 | 1.2067 | 0.7676 | 0.026* | |
O1A | 0.3796 (7) | 0.6955 (7) | 0.39805 (19) | 0.0315 (15) | |
O2A | 0.1242 (6) | 0.6094 (6) | 0.5347 (2) | 0.0315 (14) | |
C1A | 0.2759 (9) | 0.5684 (9) | 0.4724 (3) | 0.0302 (19) | |
H1A | 0.2629 | 0.6597 | 0.4667 | 0.036* | |
C2A | 0.3485 (9) | 0.4997 (6) | 0.4401 (3) | 0.016 (2) | |
C3A | 0.4058 (9) | 0.5748 (9) | 0.4033 (3) | 0.0282 (18) | |
C4A | 0.5040 (10) | 0.5033 (7) | 0.3713 (3) | 0.017 (2) | |
C5A | 0.5643 (8) | 0.5804 (9) | 0.3402 (3) | 0.0274 (18) | |
H5A | 0.5401 | 0.6712 | 0.3392 | 0.033* | |
C6A | 0.6634 (9) | 0.5310 (11) | 0.3084 (3) | 0.0291 (19) | |
C7A | 0.7484 (11) | 0.5075 (7) | 0.2786 (3) | 0.0202 (19) | |
C8A | 0.3756 (9) | 0.3530 (8) | 0.4451 (3) | 0.0281 (18) | |
H8AA | 0.4591 | 0.3385 | 0.4638 | 0.034* | |
H8AB | 0.2950 | 0.3102 | 0.4598 | 0.034* | |
C9A | 0.3981 (8) | 0.2935 (9) | 0.3996 (3) | 0.0204 (17) | |
H9AA | 0.3128 | 0.3055 | 0.3815 | 0.024* | |
H9AB | 0.4151 | 0.1977 | 0.4026 | 0.024* | |
C10A | 0.5218 (10) | 0.3571 (9) | 0.3756 (3) | 0.033 (2) | |
H10C | 0.6084 | 0.3383 | 0.3924 | 0.040* | |
H10D | 0.5313 | 0.3178 | 0.3457 | 0.040* | |
C11A | 0.2152 (11) | 0.5197 (9) | 0.5149 (3) | 0.029 (2) | |
C12A | 0.2334 (9) | 0.4121 (9) | 0.5398 (3) | 0.0318 (19) | |
H12A | 0.2915 | 0.3385 | 0.5338 | 0.038* | |
C13A | 0.1435 (9) | 0.4330 (9) | 0.5787 (3) | 0.0249 (18) | |
H13A | 0.1247 | 0.3723 | 0.6020 | 0.030* | |
C14A | 0.0934 (12) | 0.5561 (10) | 0.5743 (3) | 0.042 (3) | |
H14A | 0.0419 | 0.6003 | 0.5967 | 0.050* | |
C15A | 0.8550 (10) | 0.4980 (7) | 0.2462 (3) | 0.020 (2) | |
C16A | 0.8974 (9) | 0.3730 (9) | 0.2290 (3) | 0.0210 (19) | |
H16A | 0.8573 | 0.2938 | 0.2400 | 0.025* | |
C17A | 0.9965 (9) | 0.3696 (9) | 0.1966 (3) | 0.0230 (19) | |
H17A | 1.0242 | 0.2870 | 0.1846 | 0.028* | |
C18A | 1.0583 (11) | 0.4853 (9) | 0.1805 (3) | 0.026 (2) | |
H18A | 1.1288 | 0.4810 | 0.1584 | 0.032* | |
C19A | 1.0158 (10) | 0.6057 (10) | 0.1972 (3) | 0.029 (2) | |
H19A | 1.0578 | 0.6844 | 0.1865 | 0.035* | |
C20A | 0.9121 (9) | 0.6127 (9) | 0.2294 (3) | 0.0230 (19) | |
H20A | 0.8807 | 0.6960 | 0.2398 | 0.028* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.030 (3) | 0.016 (3) | 0.024 (3) | −0.004 (3) | 0.004 (2) | 0.000 (3) |
O2 | 0.060 (4) | 0.015 (3) | 0.021 (3) | −0.002 (3) | 0.013 (3) | 0.000 (2) |
C1 | 0.027 (4) | 0.023 (4) | 0.027 (4) | 0.002 (3) | 0.003 (3) | 0.003 (4) |
C2 | 0.022 (5) | 0.016 (5) | 0.010 (3) | 0.001 (3) | 0.004 (3) | 0.002 (2) |
C3 | 0.035 (5) | 0.021 (4) | 0.029 (4) | 0.001 (4) | −0.002 (3) | 0.005 (3) |
C4 | 0.015 (4) | 0.011 (4) | 0.025 (5) | −0.004 (3) | −0.001 (3) | 0.000 (3) |
C5 | 0.030 (4) | 0.030 (5) | 0.025 (4) | −0.003 (4) | −0.001 (3) | 0.006 (4) |
C6 | 0.036 (5) | 0.031 (5) | 0.030 (4) | −0.003 (4) | −0.006 (4) | −0.004 (4) |
C7 | 0.023 (5) | 0.030 (5) | 0.020 (4) | 0.003 (3) | 0.006 (4) | 0.007 (4) |
C8 | 0.037 (5) | 0.019 (4) | 0.034 (4) | −0.002 (4) | 0.005 (4) | 0.001 (4) |
C9 | 0.023 (4) | 0.015 (4) | 0.015 (3) | 0.002 (3) | 0.002 (3) | −0.002 (3) |
C10 | 0.034 (4) | 0.028 (5) | 0.026 (4) | 0.002 (4) | 0.003 (3) | 0.002 (3) |
C11 | 0.010 (4) | 0.030 (4) | 0.006 (3) | −0.001 (3) | 0.001 (3) | 0.000 (3) |
C12 | 0.081 (7) | 0.017 (4) | 0.019 (4) | −0.021 (5) | 0.015 (4) | −0.006 (3) |
C13 | 0.087 (8) | 0.030 (6) | 0.022 (4) | 0.017 (5) | 0.018 (5) | 0.000 (4) |
C14 | 0.032 (5) | 0.036 (6) | 0.017 (4) | 0.007 (4) | 0.003 (3) | 0.002 (4) |
C15 | 0.009 (4) | 0.028 (5) | 0.016 (4) | −0.002 (3) | 0.002 (3) | −0.002 (3) |
C16 | 0.032 (5) | 0.020 (5) | 0.017 (4) | 0.007 (4) | −0.009 (3) | −0.011 (4) |
C17 | 0.028 (4) | 0.026 (5) | 0.015 (4) | −0.007 (4) | −0.003 (3) | 0.001 (3) |
C18 | 0.021 (5) | 0.034 (6) | 0.014 (4) | 0.002 (3) | −0.002 (4) | 0.003 (3) |
C19 | 0.026 (4) | 0.031 (5) | 0.010 (3) | 0.007 (4) | 0.002 (3) | −0.002 (3) |
C20 | 0.028 (5) | 0.022 (5) | 0.016 (4) | −0.006 (4) | −0.007 (3) | 0.003 (3) |
O1A | 0.049 (4) | 0.022 (4) | 0.024 (3) | 0.008 (3) | 0.005 (3) | 0.007 (3) |
O2A | 0.033 (3) | 0.028 (3) | 0.034 (3) | 0.006 (3) | 0.003 (3) | 0.004 (3) |
C1A | 0.034 (5) | 0.030 (5) | 0.026 (4) | 0.007 (4) | −0.005 (3) | 0.003 (4) |
C2A | 0.012 (4) | 0.017 (5) | 0.017 (4) | −0.001 (3) | −0.009 (3) | 0.001 (3) |
C3A | 0.035 (5) | 0.027 (4) | 0.023 (4) | −0.004 (4) | −0.003 (3) | −0.001 (3) |
C4A | 0.016 (4) | 0.027 (5) | 0.009 (3) | −0.001 (3) | −0.006 (3) | −0.002 (3) |
C5A | 0.031 (5) | 0.025 (4) | 0.026 (4) | 0.006 (4) | 0.001 (3) | 0.001 (3) |
C6A | 0.026 (4) | 0.049 (5) | 0.012 (4) | −0.006 (4) | 0.002 (3) | −0.002 (4) |
C7A | 0.020 (4) | 0.028 (5) | 0.013 (3) | −0.002 (3) | −0.008 (3) | 0.002 (3) |
C8A | 0.041 (5) | 0.020 (4) | 0.024 (4) | 0.000 (4) | 0.002 (3) | 0.000 (3) |
C9A | 0.028 (4) | 0.016 (4) | 0.018 (4) | −0.003 (3) | 0.000 (3) | −0.006 (3) |
C10A | 0.041 (5) | 0.024 (5) | 0.035 (4) | 0.002 (4) | 0.003 (4) | −0.006 (4) |
C11A | 0.029 (5) | 0.029 (5) | 0.029 (5) | 0.007 (4) | 0.002 (4) | −0.002 (4) |
C12A | 0.025 (4) | 0.031 (5) | 0.039 (4) | −0.001 (4) | 0.003 (4) | −0.006 (4) |
C13A | 0.037 (5) | 0.017 (4) | 0.021 (4) | −0.001 (3) | 0.006 (3) | 0.007 (3) |
C14A | 0.087 (8) | 0.019 (5) | 0.019 (4) | 0.021 (5) | 0.020 (4) | 0.006 (4) |
C15A | 0.025 (5) | 0.021 (5) | 0.015 (4) | −0.001 (3) | −0.004 (4) | 0.000 (3) |
C16A | 0.024 (4) | 0.016 (4) | 0.023 (4) | 0.005 (3) | 0.009 (3) | 0.004 (3) |
C17A | 0.025 (4) | 0.018 (4) | 0.026 (4) | 0.004 (3) | 0.006 (3) | 0.000 (4) |
C18A | 0.028 (5) | 0.036 (6) | 0.015 (4) | −0.001 (4) | 0.004 (4) | 0.002 (3) |
C19A | 0.037 (5) | 0.024 (5) | 0.027 (4) | −0.009 (4) | 0.005 (4) | 0.008 (4) |
C20A | 0.025 (4) | 0.020 (5) | 0.024 (4) | −0.007 (4) | 0.006 (3) | 0.001 (4) |
O1—C3 | 1.249 (10) | O1A—C3A | 1.260 (11) |
O2—C11 | 1.418 (10) | O2A—C11A | 1.395 (11) |
O2—C14 | 1.384 (9) | O2A—C14A | 1.340 (10) |
C1—H1 | 0.9500 | C1A—H1A | 0.9500 |
C1—C2 | 1.317 (11) | C1A—C2A | 1.385 (12) |
C1—C11 | 1.438 (11) | C1A—C11A | 1.488 (13) |
C2—C3 | 1.541 (12) | C2A—C3A | 1.452 (12) |
C2—C8 | 1.512 (10) | C2A—C8A | 1.519 (10) |
C3—C4 | 1.480 (12) | C3A—C4A | 1.528 (12) |
C4—C5 | 1.387 (12) | C4A—C5A | 1.351 (12) |
C4—C10 | 1.494 (11) | C4A—C10A | 1.499 (11) |
C5—H5 | 0.9500 | C5A—H5A | 0.9500 |
C5—C6 | 1.427 (12) | C5A—C6A | 1.438 (12) |
C6—C7 | 1.203 (13) | C6A—C7A | 1.234 (13) |
C7—C15 | 1.464 (13) | C7A—C15A | 1.416 (14) |
C8—H8A | 0.9900 | C8A—H8AA | 0.9900 |
C8—H8B | 0.9900 | C8A—H8AB | 0.9900 |
C8—C9 | 1.534 (12) | C8A—C9A | 1.513 (11) |
C9—H9A | 0.9900 | C9A—H9AA | 0.9900 |
C9—H9B | 0.9900 | C9A—H9AB | 0.9900 |
C9—C10 | 1.570 (11) | C9A—C10A | 1.530 (12) |
C10—H10A | 0.9900 | C10A—H10C | 0.9900 |
C10—H10B | 0.9900 | C10A—H10D | 0.9900 |
C11—C12 | 1.333 (11) | C11A—C12A | 1.335 (13) |
C12—H12 | 0.9500 | C12A—H12A | 0.9500 |
C12—C13 | 1.435 (12) | C12A—C13A | 1.466 (11) |
C13—H13 | 0.9500 | C13A—H13A | 0.9500 |
C13—C14 | 1.292 (16) | C13A—C14A | 1.345 (14) |
C14—H14 | 0.9500 | C14A—H14A | 0.9500 |
C15—C16 | 1.393 (12) | C15A—C16A | 1.428 (12) |
C15—C20 | 1.409 (13) | C15A—C20A | 1.382 (12) |
C16—H16 | 0.9500 | C16A—H16A | 0.9500 |
C16—C17 | 1.423 (12) | C16A—C17A | 1.363 (11) |
C17—H17 | 0.9500 | C17A—H17A | 0.9500 |
C17—C18 | 1.383 (12) | C17A—C18A | 1.401 (13) |
C18—H18 | 0.9500 | C18A—H18A | 0.9500 |
C18—C19 | 1.397 (12) | C18A—C19A | 1.382 (14) |
C19—H19 | 0.9500 | C19A—H19A | 0.9500 |
C19—C20 | 1.394 (12) | C19A—C20A | 1.390 (12) |
C20—H20 | 0.9500 | C20A—H20A | 0.9500 |
C14—O2—C11 | 106.5 (6) | C14A—O2A—C11A | 104.7 (7) |
C2—C1—H1 | 117.6 | C2A—C1A—H1A | 115.4 |
C2—C1—C11 | 124.7 (8) | C2A—C1A—C11A | 129.3 (8) |
C11—C1—H1 | 117.6 | C11A—C1A—H1A | 115.4 |
C1—C2—C3 | 117.2 (7) | C1A—C2A—C3A | 117.5 (7) |
C1—C2—C8 | 126.7 (8) | C1A—C2A—C8A | 120.6 (8) |
C8—C2—C3 | 116.1 (7) | C3A—C2A—C8A | 121.7 (8) |
O1—C3—C2 | 120.4 (7) | O1A—C3A—C2A | 122.0 (8) |
O1—C3—C4 | 120.8 (7) | O1A—C3A—C4A | 120.4 (7) |
C4—C3—C2 | 118.7 (7) | C2A—C3A—C4A | 117.6 (7) |
C3—C4—C10 | 121.9 (8) | C5A—C4A—C3A | 115.2 (7) |
C5—C4—C3 | 116.3 (7) | C5A—C4A—C10A | 125.7 (8) |
C5—C4—C10 | 121.6 (8) | C10A—C4A—C3A | 119.0 (8) |
C4—C5—H5 | 116.2 | C4A—C5A—H5A | 118.6 |
C4—C5—C6 | 127.6 (9) | C4A—C5A—C6A | 122.9 (8) |
C6—C5—H5 | 116.2 | C6A—C5A—H5A | 118.6 |
C7—C6—C5 | 174.5 (11) | C7A—C6A—C5A | 170.5 (10) |
C6—C7—C15 | 171.9 (10) | C6A—C7A—C15A | 171.7 (9) |
C2—C8—H8A | 109.3 | C2A—C8A—H8AA | 109.9 |
C2—C8—H8B | 109.3 | C2A—C8A—H8AB | 109.9 |
C2—C8—C9 | 111.7 (7) | H8AA—C8A—H8AB | 108.3 |
H8A—C8—H8B | 107.9 | C9A—C8A—C2A | 108.9 (7) |
C9—C8—H8A | 109.3 | C9A—C8A—H8AA | 109.9 |
C9—C8—H8B | 109.3 | C9A—C8A—H8AB | 109.9 |
C8—C9—H9A | 109.9 | C8A—C9A—H9AA | 109.3 |
C8—C9—H9B | 109.9 | C8A—C9A—H9AB | 109.3 |
C8—C9—C10 | 108.9 (7) | C8A—C9A—C10A | 111.6 (7) |
H9A—C9—H9B | 108.3 | H9AA—C9A—H9AB | 108.0 |
C10—C9—H9A | 109.9 | C10A—C9A—H9AA | 109.3 |
C10—C9—H9B | 109.9 | C10A—C9A—H9AB | 109.3 |
C4—C10—C9 | 108.3 (7) | C4A—C10A—C9A | 111.7 (7) |
C4—C10—H10A | 110.0 | C4A—C10A—H10C | 109.3 |
C4—C10—H10B | 110.0 | C4A—C10A—H10D | 109.3 |
C9—C10—H10A | 110.0 | C9A—C10A—H10C | 109.3 |
C9—C10—H10B | 110.0 | C9A—C10A—H10D | 109.3 |
H10A—C10—H10B | 108.4 | H10C—C10A—H10D | 107.9 |
O2—C11—C1 | 111.3 (7) | O2A—C11A—C1A | 113.2 (8) |
C12—C11—O2 | 107.0 (7) | C12A—C11A—O2A | 112.0 (9) |
C12—C11—C1 | 141.6 (8) | C12A—C11A—C1A | 134.6 (9) |
C11—C12—H12 | 125.8 | C11A—C12A—H12A | 127.7 |
C11—C12—C13 | 108.4 (8) | C11A—C12A—C13A | 104.6 (8) |
C13—C12—H12 | 125.8 | C13A—C12A—H12A | 127.7 |
C12—C13—H13 | 126.2 | C12A—C13A—H13A | 127.3 |
C14—C13—C12 | 107.5 (8) | C14A—C13A—C12A | 105.4 (7) |
C14—C13—H13 | 126.2 | C14A—C13A—H13A | 127.3 |
O2—C14—H14 | 124.7 | O2A—C14A—C13A | 112.5 (7) |
C13—C14—O2 | 110.5 (8) | O2A—C14A—H14A | 123.7 |
C13—C14—H14 | 124.7 | C13A—C14A—H14A | 123.7 |
C16—C15—C7 | 122.7 (8) | C7A—C15A—C16A | 121.0 (7) |
C16—C15—C20 | 117.9 (9) | C20A—C15A—C7A | 118.7 (7) |
C20—C15—C7 | 119.3 (7) | C20A—C15A—C16A | 120.2 (9) |
C15—C16—H16 | 119.7 | C15A—C16A—H16A | 120.6 |
C15—C16—C17 | 120.6 (8) | C17A—C16A—C15A | 118.7 (9) |
C17—C16—H16 | 119.7 | C17A—C16A—H16A | 120.6 |
C16—C17—H17 | 120.1 | C16A—C17A—H17A | 119.3 |
C18—C17—C16 | 119.8 (9) | C16A—C17A—C18A | 121.4 (9) |
C18—C17—H17 | 120.1 | C18A—C17A—H17A | 119.3 |
C17—C18—H18 | 119.7 | C17A—C18A—H18A | 120.3 |
C17—C18—C19 | 120.6 (9) | C19A—C18A—C17A | 119.4 (9) |
C19—C18—H18 | 119.7 | C19A—C18A—H18A | 120.3 |
C18—C19—H19 | 120.5 | C18A—C19A—H19A | 119.7 |
C20—C19—C18 | 119.1 (9) | C18A—C19A—C20A | 120.6 (9) |
C20—C19—H19 | 120.5 | C20A—C19A—H19A | 119.7 |
C15—C20—H20 | 119.0 | C15A—C20A—C19A | 119.7 (9) |
C19—C20—C15 | 122.0 (9) | C15A—C20A—H20A | 120.2 |
C19—C20—H20 | 119.0 | C19A—C20A—H20A | 120.2 |
O1—C3—C4—C5 | 11.0 (13) | O1A—C3A—C4A—C5A | 4.0 (12) |
O1—C3—C4—C10 | −173.8 (8) | O1A—C3A—C4A—C10A | −173.9 (8) |
O2—C11—C12—C13 | 0.3 (11) | O2A—C11A—C12A—C13A | 1.4 (11) |
C1—C2—C3—O1 | −2.1 (13) | C1A—C2A—C3A—O1A | −7.1 (13) |
C1—C2—C3—C4 | 175.1 (8) | C1A—C2A—C3A—C4A | 171.1 (7) |
C1—C2—C8—C9 | 148.5 (9) | C1A—C2A—C8A—C9A | 156.0 (8) |
C1—C11—C12—C13 | 173.9 (11) | C1A—C11A—C12A—C13A | 177.2 (11) |
C2—C1—C11—O2 | −172.2 (8) | C2A—C1A—C11A—O2A | −167.1 (8) |
C2—C1—C11—C12 | 14.3 (19) | C2A—C1A—C11A—C12A | 17.1 (19) |
C2—C3—C4—C5 | −166.2 (8) | C2A—C3A—C4A—C5A | −174.2 (7) |
C2—C3—C4—C10 | 9.0 (13) | C2A—C3A—C4A—C10A | 8.0 (12) |
C2—C8—C9—C10 | 63.7 (9) | C2A—C8A—C9A—C10A | 59.4 (9) |
C3—C2—C8—C9 | −28.3 (10) | C3A—C2A—C8A—C9A | −28.6 (11) |
C3—C4—C5—C6 | 177.8 (8) | C3A—C4A—C5A—C6A | 177.6 (7) |
C3—C4—C10—C9 | 25.1 (12) | C3A—C4A—C10A—C9A | 22.1 (12) |
C5—C4—C10—C9 | −160.0 (8) | C5A—C4A—C10A—C9A | −155.5 (9) |
C7—C15—C16—C17 | −176.4 (9) | C7A—C15A—C16A—C17A | 177.4 (9) |
C7—C15—C20—C19 | 176.5 (9) | C7A—C15A—C20A—C19A | −179.3 (9) |
C8—C2—C3—O1 | 175.0 (8) | C8A—C2A—C3A—O1A | 177.4 (8) |
C8—C2—C3—C4 | −7.8 (12) | C8A—C2A—C3A—C4A | −4.5 (12) |
C8—C9—C10—C4 | −60.7 (9) | C8A—C9A—C10A—C4A | −57.1 (10) |
C10—C4—C5—C6 | 2.6 (14) | C10A—C4A—C5A—C6A | −4.6 (14) |
C11—O2—C14—C13 | 1.9 (10) | C11A—O2A—C14A—C13A | −7.8 (12) |
C11—C1—C2—C3 | −178.5 (7) | C11A—C1A—C2A—C3A | −175.2 (8) |
C11—C1—C2—C8 | 4.8 (15) | C11A—C1A—C2A—C8A | 0.3 (14) |
C11—C12—C13—C14 | 0.9 (13) | C11A—C12A—C13A—C14A | −5.9 (11) |
C12—C13—C14—O2 | −1.7 (12) | C12A—C13A—C14A—O2A | 8.7 (12) |
C14—O2—C11—C1 | −177.0 (7) | C14A—O2A—C11A—C1A | −173.1 (9) |
C14—O2—C11—C12 | −1.3 (9) | C14A—O2A—C11A—C12A | 3.6 (11) |
C15—C16—C17—C18 | 0.0 (13) | C15A—C16A—C17A—C18A | 1.1 (13) |
C16—C15—C20—C19 | 0.0 (13) | C16A—C15A—C20A—C19A | −3.0 (14) |
C16—C17—C18—C19 | 0.0 (14) | C16A—C17A—C18A—C19A | −1.5 (15) |
C17—C18—C19—C20 | 0.0 (13) | C17A—C18A—C19A—C20A | −0.4 (15) |
C18—C19—C20—C15 | 0.0 (12) | C18A—C19A—C20A—C15A | 2.6 (14) |
C20—C15—C16—C17 | 0.0 (13) | C20A—C15A—C16A—C17A | 1.2 (14) |
C18H20O2 | Z = 2 |
Mr = 268.34 | F(000) = 288 |
Triclinic, P1 | Dx = 1.203 Mg m−3 |
a = 9.2801 (14) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.5498 (14) Å | Cell parameters from 2852 reflections |
c = 9.6407 (14) Å | θ = 2.3–34.7° |
α = 84.218 (3)° | µ = 0.08 mm−1 |
β = 70.882 (3)° | T = 120 K |
γ = 66.632 (3)° | Prism, yellow |
V = 740.63 (19) Å3 | 0.4 × 0.3 × 0.2 mm |
Bruker SMART APEX CCD area detector diffractometer | 6779 independent reflections |
Radiation source: sealed tube | 4496 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
Detector resolution: 8 pixels mm-1 | θmax = 36.1°, θmin = 2.3° |
ω and φ scans | h = −15→15 |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | k = −15→15 |
Tmin = 0.669, Tmax = 0.747 | l = −15→15 |
13735 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.139 | w = 1/[σ2(Fo2) + (0.050P)2 + 0.150P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
6779 reflections | Δρmax = 0.45 e Å−3 |
182 parameters | Δρmin = −0.32 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 | 0.23655 (10) | 0.69376 (8) | 0.12731 (9) | 0.02436 (17) | |
O2 | 0.06610 (10) | 0.31249 (8) | 0.04610 (9) | 0.02500 (17) | |
C1 | 0.33819 (12) | 0.58373 (11) | 0.16766 (11) | 0.01795 (18) | |
C2 | 0.46380 (12) | 0.60414 (11) | 0.21891 (11) | 0.01820 (18) | |
C3 | 0.60114 (13) | 0.46600 (12) | 0.24468 (13) | 0.0239 (2) | |
H3A | 0.6485 | 0.4939 | 0.3108 | 0.029* | |
H3B | 0.6898 | 0.4268 | 0.1502 | 0.029* | |
C4 | 0.53785 (15) | 0.34239 (12) | 0.31322 (13) | 0.0248 (2) | |
H4A | 0.4514 | 0.3808 | 0.4090 | 0.030* | |
H4B | 0.6297 | 0.2524 | 0.3310 | 0.030* | |
C5 | 0.46633 (13) | 0.29535 (11) | 0.21279 (12) | 0.0210 (2) | |
H5A | 0.5576 | 0.2404 | 0.1247 | 0.025* | |
H5B | 0.4148 | 0.2239 | 0.2649 | 0.025* | |
C6 | 0.33968 (12) | 0.42801 (11) | 0.16475 (11) | 0.01714 (18) | |
C7 | 0.22526 (12) | 0.41645 (11) | 0.11416 (11) | 0.01856 (18) | |
H7 | 0.1503 | 0.5099 | 0.0905 | 0.022* | |
C8 | 0.20164 (12) | 0.28237 (11) | 0.09137 (11) | 0.01880 (18) | |
C9 | 0.27716 (13) | 0.12861 (11) | 0.10131 (12) | 0.0217 (2) | |
H9 | 0.3737 | 0.0765 | 0.1294 | 0.026* | |
C10 | 0.18437 (14) | 0.06108 (12) | 0.06178 (13) | 0.0259 (2) | |
H10 | 0.2061 | −0.0447 | 0.0588 | 0.031* | |
C11 | 0.05936 (15) | 0.17637 (13) | 0.02933 (14) | 0.0282 (2) | |
H11 | −0.0225 | 0.1639 | −0.0012 | 0.034* | |
C12 | 0.44379 (13) | 0.74814 (12) | 0.24116 (12) | 0.0217 (2) | |
H12 | 0.3501 | 0.8275 | 0.2242 | 0.026* | |
C13 | 0.55011 (14) | 0.79231 (12) | 0.28780 (12) | 0.0232 (2) | |
C14 | 0.63463 (14) | 0.83827 (13) | 0.32581 (13) | 0.0250 (2) | |
C15 | 0.73884 (15) | 0.88956 (13) | 0.37614 (14) | 0.0270 (2) | |
H15A | 0.6674 | 0.9664 | 0.4573 | 0.032* | |
H15B | 0.7952 | 0.9402 | 0.2946 | 0.032* | |
C16 | 0.86873 (14) | 0.76120 (13) | 0.42901 (13) | 0.0250 (2) | |
H16A | 0.8134 | 0.7083 | 0.5088 | 0.030* | |
H16B | 0.9435 | 0.6861 | 0.3471 | 0.030* | |
C17 | 0.96963 (16) | 0.82046 (16) | 0.48471 (15) | 0.0330 (3) | |
H17A | 0.8937 | 0.9013 | 0.5613 | 0.040* | |
H17B | 1.0308 | 0.8670 | 0.4027 | 0.040* | |
C18 | 1.09177 (17) | 0.69700 (19) | 0.54821 (16) | 0.0439 (4) | |
H18A | 1.1686 | 0.6173 | 0.4726 | 0.066* | |
H18B | 1.0318 | 0.6525 | 0.6314 | 0.066* | |
H18C | 1.1539 | 0.7414 | 0.5817 | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0267 (4) | 0.0158 (3) | 0.0373 (4) | −0.0081 (3) | −0.0200 (3) | 0.0052 (3) |
O2 | 0.0258 (4) | 0.0167 (3) | 0.0397 (5) | −0.0077 (3) | −0.0207 (3) | 0.0030 (3) |
C1 | 0.0185 (4) | 0.0170 (4) | 0.0197 (4) | −0.0070 (3) | −0.0080 (3) | 0.0020 (3) |
C2 | 0.0188 (4) | 0.0185 (4) | 0.0192 (4) | −0.0078 (3) | −0.0082 (4) | 0.0029 (3) |
C3 | 0.0221 (5) | 0.0211 (5) | 0.0335 (6) | −0.0082 (4) | −0.0162 (4) | 0.0046 (4) |
C4 | 0.0293 (5) | 0.0206 (5) | 0.0306 (6) | −0.0101 (4) | −0.0184 (5) | 0.0076 (4) |
C5 | 0.0235 (5) | 0.0150 (4) | 0.0264 (5) | −0.0063 (4) | −0.0123 (4) | 0.0032 (4) |
C6 | 0.0186 (4) | 0.0152 (4) | 0.0185 (4) | −0.0068 (3) | −0.0070 (3) | 0.0019 (3) |
C7 | 0.0195 (4) | 0.0148 (4) | 0.0217 (5) | −0.0062 (3) | −0.0076 (4) | 0.0017 (3) |
C8 | 0.0181 (4) | 0.0171 (4) | 0.0234 (5) | −0.0066 (3) | −0.0097 (4) | 0.0015 (3) |
C9 | 0.0218 (5) | 0.0161 (4) | 0.0296 (5) | −0.0058 (4) | −0.0132 (4) | 0.0014 (4) |
C10 | 0.0291 (5) | 0.0163 (4) | 0.0377 (6) | −0.0085 (4) | −0.0178 (5) | 0.0011 (4) |
C11 | 0.0312 (6) | 0.0200 (5) | 0.0434 (7) | −0.0118 (4) | −0.0219 (5) | 0.0015 (4) |
C12 | 0.0230 (5) | 0.0206 (5) | 0.0257 (5) | −0.0096 (4) | −0.0119 (4) | 0.0025 (4) |
C13 | 0.0259 (5) | 0.0206 (5) | 0.0265 (5) | −0.0102 (4) | −0.0115 (4) | 0.0020 (4) |
C14 | 0.0272 (5) | 0.0237 (5) | 0.0281 (5) | −0.0111 (4) | −0.0120 (4) | 0.0005 (4) |
C15 | 0.0291 (6) | 0.0259 (5) | 0.0338 (6) | −0.0138 (4) | −0.0150 (5) | −0.0015 (4) |
C16 | 0.0226 (5) | 0.0272 (5) | 0.0284 (5) | −0.0115 (4) | −0.0091 (4) | −0.0007 (4) |
C17 | 0.0296 (6) | 0.0426 (7) | 0.0345 (6) | −0.0175 (5) | −0.0144 (5) | −0.0028 (5) |
C18 | 0.0293 (7) | 0.0655 (10) | 0.0373 (7) | −0.0153 (7) | −0.0158 (6) | 0.0046 (7) |
O1—C1 | 1.2317 (12) | C9—C10 | 1.4169 (15) |
O2—C8 | 1.3793 (12) | C10—H10 | 0.9500 |
O2—C11 | 1.3540 (13) | C10—C11 | 1.3457 (15) |
C1—C2 | 1.4892 (14) | C11—H11 | 0.9500 |
C1—C6 | 1.4847 (13) | C12—H12 | 0.9500 |
C2—C3 | 1.4947 (14) | C12—C13 | 1.4187 (15) |
C2—C12 | 1.3424 (14) | C13—C14 | 1.1982 (15) |
C3—H3A | 0.9900 | C14—C15 | 1.4635 (15) |
C3—H3B | 0.9900 | C15—H15A | 0.9900 |
C3—C4 | 1.5211 (15) | C15—H15B | 0.9900 |
C4—H4A | 0.9900 | C15—C16 | 1.5231 (16) |
C4—H4B | 0.9900 | C16—H16A | 0.9900 |
C4—C5 | 1.5248 (15) | C16—H16B | 0.9900 |
C5—H5A | 0.9900 | C16—C17 | 1.5154 (16) |
C5—H5B | 0.9900 | C17—H17A | 0.9900 |
C5—C6 | 1.5026 (13) | C17—H17B | 0.9900 |
C6—C7 | 1.3494 (14) | C17—C18 | 1.5161 (19) |
C7—H7 | 0.9500 | C18—H18A | 0.9800 |
C7—C8 | 1.4306 (14) | C18—H18B | 0.9800 |
C8—C9 | 1.3623 (14) | C18—H18C | 0.9800 |
C9—H9 | 0.9500 | ||
C11—O2—C8 | 106.96 (8) | C10—C9—H9 | 126.5 |
O1—C1—C2 | 120.48 (9) | C9—C10—H10 | 126.8 |
O1—C1—C6 | 120.95 (9) | C11—C10—C9 | 106.45 (9) |
C6—C1—C2 | 118.56 (8) | C11—C10—H10 | 126.8 |
C1—C2—C3 | 119.03 (9) | O2—C11—H11 | 124.6 |
C12—C2—C1 | 116.87 (9) | C10—C11—O2 | 110.78 (10) |
C12—C2—C3 | 124.09 (9) | C10—C11—H11 | 124.6 |
C2—C3—H3A | 109.6 | C2—C12—H12 | 117.1 |
C2—C3—H3B | 109.6 | C2—C12—C13 | 125.79 (10) |
C2—C3—C4 | 110.44 (9) | C13—C12—H12 | 117.1 |
H3A—C3—H3B | 108.1 | C14—C13—C12 | 176.18 (12) |
C4—C3—H3A | 109.6 | C13—C14—C15 | 177.80 (12) |
C4—C3—H3B | 109.6 | C14—C15—H15A | 108.8 |
C3—C4—H4A | 109.5 | C14—C15—H15B | 108.8 |
C3—C4—H4B | 109.5 | C14—C15—C16 | 113.67 (9) |
C3—C4—C5 | 110.80 (9) | H15A—C15—H15B | 107.7 |
H4A—C4—H4B | 108.1 | C16—C15—H15A | 108.8 |
C5—C4—H4A | 109.5 | C16—C15—H15B | 108.8 |
C5—C4—H4B | 109.5 | C15—C16—H16A | 109.3 |
C4—C5—H5A | 108.9 | C15—C16—H16B | 109.3 |
C4—C5—H5B | 108.9 | H16A—C16—H16B | 107.9 |
H5A—C5—H5B | 107.7 | C17—C16—C15 | 111.74 (10) |
C6—C5—C4 | 113.29 (8) | C17—C16—H16A | 109.3 |
C6—C5—H5A | 108.9 | C17—C16—H16B | 109.3 |
C6—C5—H5B | 108.9 | C16—C17—H17A | 109.0 |
C1—C6—C5 | 119.92 (9) | C16—C17—H17B | 109.0 |
C7—C6—C1 | 115.73 (8) | C16—C17—C18 | 113.00 (12) |
C7—C6—C5 | 124.33 (9) | H17A—C17—H17B | 107.8 |
C6—C7—H7 | 115.7 | C18—C17—H17A | 109.0 |
C6—C7—C8 | 128.70 (9) | C18—C17—H17B | 109.0 |
C8—C7—H7 | 115.7 | C17—C18—H18A | 109.5 |
O2—C8—C7 | 113.56 (8) | C17—C18—H18B | 109.5 |
C9—C8—O2 | 108.80 (9) | C17—C18—H18C | 109.5 |
C9—C8—C7 | 137.64 (10) | H18A—C18—H18B | 109.5 |
C8—C9—H9 | 126.5 | H18A—C18—H18C | 109.5 |
C8—C9—C10 | 107.02 (9) | H18B—C18—H18C | 109.5 |
R1 | R2 | n | α1 | α2 | r1 | r2 | r3 | |
3a | Ph | H | 0 | 6.76 (8) | 1.46 (8) | 1.340 (4)–1.346 (4) | 1.470 (3)–1.474 (3) | 1.413 (4)–1.415 (4) |
3b | 4-BrC6H4 | H | 1 | 3.20 (6) | 59.50 (6) | 1.360 (12) | 1.490 (2)–1.510 (2) | 1.420 (2)–1.430 (2) |
3c | Ph | H | 0 | 7.72 (8) | 10.79 (8) | 1.337 (3)–1.338 (3) | 1.483 (3)–1.488 (3) | 1.413 (3)–1.416 (3) |
3d | 4-BrC6H4 | H | 1 | 5.30 (4) | 5.30 (4) | 1.348 (12) | 1.487 (9)–1.489 (11) | 1.405 (13) |
3e | Ph | t-Bu | 1 | 36.53 (8) | 27.78 (8) | 1.323 (2)–1.346 (2) | 1.478 (2)–1.483 (2) | 1.416 (2)–1.417 (2) |
3f | 4-MeC6H4 | t-Bu | 1 | 9.00 (4) | 24.50 (4) | 1.34 (1)–1.37 (1) | 1.50 (1)–1.52 (1) | 1.42 (1)–1.44 (2) |
5a | Ph | H | 1 | 8.10–9.90 (4) | 13.70–17.10 (3) | 1.32 (1)–1.39 (1) | 1.45 (2)–1.54 (1) | 1.43 (1)–1.44 (1) |
5b | n-Bu | H | 1 | 1.61 (7) | 5.46 (4) | 1.348 (3)–1.353 (3) | 1.490 (3)–1.493 (3) | 1.422 (3)–1.436 (3) |
Note: (a) geometrical parameters are depicted in Scheme 2. |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- Purchase subscription
- Reduced-price subscriptions
- If you have already subscribed, you may need to register