We have determined the crystal structures of 2,2'-(4-fluorophenyl)methylenebis(3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one), C23H27FO4, (I), 2,2'-(4-chlorophenyl)methylenebis(3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one), C23H27ClO4, (II), 2,2'-(4-hydroxyphenyl)methylenebis(3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one), C23H28O5, (III), 2,2'-(4-methylphenyl)methylenebis(3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one), C24H30O4, (IV), 2,2'-(4-methoxyphenyl)methylenebis(3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one), C24H30O5, (V), and 2,2'-(4-N,N'-dimethylaminophenyl)methylenebis(3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one), C25H33NO4, (VI). Structures (III) to (VI) of these bis-dimedone derivatives show nearly the same packing pattern irrespective of the different substituent in the para position of the aromatic ring. However, (II) does not fit into this scheme, although the Cl atom is a substituent not too different from the others. The different packing of the fluoro compound, (I), can be explained by the fact that it crystallizes with two molecules in the asymmetric unit, which show a different conformation of the dimedone ring. On the other hand, (I) shows a similar packing pattern to bis(2-hydroxy-4,4-dimethyl-6-oxo-1-cyclohexenyl)phenylmethane, a compound containing an aromatic ring without any substituent and with Z' = 2.
Supporting information
CCDC references: 163921; 163922; 163923; 163924; 163925; 163926
For all compounds, data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1991).
Crystal data top
C23H27FO4 | Dx = 1.249 Mg m−3 |
Mr = 386.45 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, I41cd | Cell parameters from 8192 reflections |
Hall symbol: I 41b -2c | θ = 0–25° |
a = 21.186 (4) Å | µ = 0.09 mm−1 |
c = 36.633 (1) Å | T = 173 K |
V = 16443 (4) Å3 | Block, colourless |
Z = 32 | 0.55 × 0.40 × 0.25 mm |
F(000) = 6592 | |
Data collection top
Siemens CCD three-circle diffractometer | 4615 independent reflections |
Radiation source: fine-focus sealed tube | 3818 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.080 |
ω scans | θmax = 27.1°, θmin = 1.8° |
Absorption correction: empirical SADABS (Sheldrick, 1996) | h = −27→27 |
Tmin = 0.952, Tmax = 0.978 | k = −27→27 |
97175 measured reflections | l = −46→46 |
Refinement top
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)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.083 | w = 1/[σ2(Fo2) + (0.0294P)2 + 9.1605P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.002 |
4615 reflections | Δρmax = 0.15 e Å−3 |
521 parameters | Δρmin = −0.18 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.1 (8) |
Special details top
Experimental. ; |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 >
σ(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.64131 (12) | 0.07353 (12) | −0.03253 (7) | 0.0264 (6) | |
H1 | 0.6756 | 0.0574 | −0.0488 | 0.032* | |
C11 | 0.62550 (12) | 0.01750 (11) | −0.00758 (7) | 0.0251 (6) | |
C12 | 0.59432 (12) | 0.02247 (12) | 0.02539 (7) | 0.0261 (6) | |
O12 | 0.57074 (9) | 0.07608 (9) | 0.03784 (6) | 0.0317 (4) | |
H12 | 0.565 (2) | 0.103 (2) | 0.0173 (12) | 0.082 (14)* | |
C13 | 0.58287 (13) | −0.03217 (13) | 0.05028 (8) | 0.0299 (6) | |
H13A | 0.5389 | −0.0468 | 0.0469 | 0.036* | |
H13B | 0.5871 | −0.0175 | 0.0758 | 0.036* | |
C14 | 0.62741 (13) | −0.08851 (12) | 0.04445 (7) | 0.0288 (6) | |
C17 | 0.69266 (13) | −0.07345 (14) | 0.06026 (8) | 0.0369 (7) | |
H17A | 0.6887 | −0.0642 | 0.0864 | 0.055* | |
H17B | 0.7104 | −0.0367 | 0.0477 | 0.055* | |
H17C | 0.7206 | −0.1098 | 0.0568 | 0.055* | |
C18 | 0.60012 (15) | −0.14703 (13) | 0.06350 (9) | 0.0381 (7) | |
H18A | 0.5966 | −0.1389 | 0.0898 | 0.057* | |
H18B | 0.6281 | −0.1832 | 0.0594 | 0.057* | |
H18C | 0.5582 | −0.1563 | 0.0535 | 0.057* | |
C15 | 0.63152 (14) | −0.10161 (12) | 0.00348 (8) | 0.0317 (6) | |
H15A | 0.6665 | −0.1317 | −0.0008 | 0.038* | |
H15B | 0.5920 | −0.1226 | −0.0043 | 0.038* | |
C16 | 0.64185 (13) | −0.04440 (12) | −0.02046 (8) | 0.0286 (6) | |
O16 | 0.66217 (10) | −0.05419 (9) | −0.05248 (6) | 0.0364 (5) | |
C21 | 0.58762 (12) | 0.09124 (12) | −0.05861 (7) | 0.0256 (6) | |
C22 | 0.58420 (14) | 0.06575 (12) | −0.09319 (8) | 0.0314 (6) | |
O22 | 0.62224 (11) | 0.02072 (10) | −0.10510 (6) | 0.0422 (6) | |
H22 | 0.6409 (19) | 0.001 (2) | −0.0880 (11) | 0.075 (13)* | |
C23 | 0.53579 (15) | 0.08581 (13) | −0.12089 (8) | 0.0352 (7) | |
H23B | 0.5009 | 0.0547 | −0.1209 | 0.042* | |
H23A | 0.5554 | 0.0852 | −0.1454 | 0.042* | |
C24 | 0.50823 (14) | 0.15159 (12) | −0.11402 (8) | 0.0297 (6) | |
C27 | 0.55671 (16) | 0.20317 (14) | −0.12266 (8) | 0.0396 (7) | |
H27A | 0.5940 | 0.1976 | −0.1071 | 0.059* | |
H27B | 0.5380 | 0.2447 | −0.1180 | 0.059* | |
H27C | 0.5692 | 0.2002 | −0.1484 | 0.059* | |
C28 | 0.45018 (16) | 0.16086 (15) | −0.13847 (8) | 0.0410 (8) | |
H28A | 0.4187 | 0.1284 | −0.1329 | 0.061* | |
H28B | 0.4627 | 0.1574 | −0.1641 | 0.061* | |
H28C | 0.4320 | 0.2027 | −0.1340 | 0.061* | |
C25 | 0.48821 (13) | 0.15400 (13) | −0.07381 (7) | 0.0300 (6) | |
H25A | 0.4768 | 0.1981 | −0.0677 | 0.036* | |
H25B | 0.4498 | 0.1279 | −0.0708 | 0.036* | |
C26 | 0.53725 (13) | 0.13156 (12) | −0.04702 (7) | 0.0262 (6) | |
O26 | 0.53063 (9) | 0.14874 (8) | −0.01408 (5) | 0.0288 (4) | |
C31 | 0.67098 (12) | 0.13052 (12) | −0.01288 (7) | 0.0272 (6) | |
C32 | 0.70302 (13) | 0.12332 (14) | 0.02013 (8) | 0.0357 (7) | |
H32 | 0.7043 | 0.0830 | 0.0315 | 0.043* | |
C33 | 0.73317 (14) | 0.17419 (15) | 0.03677 (9) | 0.0422 (7) | |
H33 | 0.7545 | 0.1692 | 0.0594 | 0.051* | |
C34 | 0.73119 (15) | 0.23164 (15) | 0.01957 (9) | 0.0427 (8) | |
F34 | 0.76126 (10) | 0.28159 (9) | 0.03575 (6) | 0.0654 (6) | |
C35 | 0.70154 (15) | 0.24074 (14) | −0.01287 (10) | 0.0422 (8) | |
H35 | 0.7013 | 0.2811 | −0.0241 | 0.051* | |
C36 | 0.67152 (13) | 0.18984 (13) | −0.02927 (9) | 0.0345 (7) | |
H36 | 0.6510 | 0.1956 | −0.0521 | 0.041* | |
C1A | 0.87922 (13) | 0.35785 (13) | 0.21317 (7) | 0.0302 (6) | |
H1A | 0.8831 | 0.3225 | 0.2311 | 0.036* | |
C11A | 0.85848 (13) | 0.41431 (13) | 0.23621 (7) | 0.0297 (6) | |
C12A | 0.83356 (12) | 0.46925 (13) | 0.22292 (7) | 0.0280 (6) | |
O12A | 0.82506 (9) | 0.48122 (9) | 0.18756 (6) | 0.0323 (5) | |
H12A | 0.8454 (17) | 0.4565 (17) | 0.1735 (10) | 0.051 (11)* | |
C13A | 0.81175 (13) | 0.52337 (14) | 0.24653 (8) | 0.0345 (7) | |
H13C | 0.7653 | 0.5213 | 0.2490 | 0.041* | |
H13D | 0.8223 | 0.5636 | 0.2342 | 0.041* | |
C14A | 0.84128 (14) | 0.52348 (14) | 0.28484 (8) | 0.0372 (7) | |
C17A | 0.91120 (15) | 0.54312 (16) | 0.28327 (9) | 0.0467 (8) | |
H17D | 0.9145 | 0.5862 | 0.2737 | 0.070* | |
H17E | 0.9343 | 0.5142 | 0.2672 | 0.070* | |
H17F | 0.9293 | 0.5415 | 0.3079 | 0.070* | |
C18A | 0.80577 (18) | 0.5708 (2) | 0.30899 (10) | 0.0603 (11) | |
H18D | 0.8095 | 0.6132 | 0.2985 | 0.090* | |
H18E | 0.8240 | 0.5706 | 0.3336 | 0.090* | |
H18F | 0.7611 | 0.5589 | 0.3103 | 0.090* | |
C15A | 0.83603 (16) | 0.45670 (16) | 0.29977 (8) | 0.0439 (8) | |
H15C | 0.8555 | 0.4551 | 0.3243 | 0.053* | |
H15D | 0.7909 | 0.4454 | 0.3023 | 0.053* | |
C16A | 0.86795 (14) | 0.40922 (15) | 0.27534 (8) | 0.0366 (7) | |
O16A | 0.90154 (11) | 0.36665 (10) | 0.28884 (6) | 0.0483 (6) | |
C21A | 0.94568 (13) | 0.36506 (13) | 0.19757 (8) | 0.0307 (6) | |
C22A | 0.99697 (15) | 0.34079 (14) | 0.21527 (9) | 0.0411 (7) | |
O22A | 0.99432 (13) | 0.31441 (12) | 0.24828 (7) | 0.0547 (6) | |
H22A | 0.964 (2) | 0.328 (2) | 0.2615 (13) | 0.096 (18)* | |
C23A | 1.06241 (15) | 0.34035 (17) | 0.19979 (11) | 0.0534 (9) | |
H23C | 1.0819 | 0.2988 | 0.2049 | 0.064* | |
H23D | 1.0877 | 0.3728 | 0.2126 | 0.064* | |
C24A | 1.06608 (14) | 0.35268 (15) | 0.15876 (11) | 0.0456 (8) | |
C27A | 1.13439 (16) | 0.36939 (19) | 0.14788 (13) | 0.0674 (12) | |
H27D | 1.1621 | 0.3336 | 0.1533 | 0.101* | |
H27E | 1.1484 | 0.4064 | 0.1618 | 0.101* | |
H27F | 1.1360 | 0.3789 | 0.1217 | 0.101* | |
C28A | 1.04535 (16) | 0.29405 (16) | 0.13723 (11) | 0.0530 (9) | |
H28D | 1.0732 | 0.2586 | 0.1432 | 0.080* | |
H28E | 1.0478 | 0.3029 | 0.1110 | 0.080* | |
H28F | 1.0018 | 0.2832 | 0.1438 | 0.080* | |
C25A | 1.02240 (14) | 0.40821 (15) | 0.14980 (10) | 0.0467 (8) | |
H25C | 1.0415 | 0.4474 | 0.1596 | 0.056* | |
H25D | 1.0198 | 0.4127 | 0.1229 | 0.056* | |
C26A | 0.95641 (13) | 0.40199 (13) | 0.16481 (8) | 0.0316 (6) | |
O26A | 0.91290 (10) | 0.43100 (9) | 0.14915 (5) | 0.0353 (5) | |
C31A | 0.82969 (13) | 0.33444 (12) | 0.18568 (7) | 0.0302 (6) | |
C32A | 0.76537 (14) | 0.34507 (13) | 0.19107 (9) | 0.0356 (7) | |
H32A | 0.7522 | 0.3699 | 0.2113 | 0.043* | |
C33A | 0.72015 (15) | 0.32037 (15) | 0.16772 (9) | 0.0405 (7) | |
H33A | 0.6765 | 0.3280 | 0.1718 | 0.049* | |
C34A | 0.73982 (15) | 0.28479 (15) | 0.13874 (9) | 0.0443 (8) | |
F34A | 0.69632 (10) | 0.26203 (11) | 0.11451 (5) | 0.0621 (6) | |
C35A | 0.80269 (16) | 0.27066 (16) | 0.13273 (9) | 0.0449 (8) | |
H35A | 0.8151 | 0.2446 | 0.1129 | 0.054* | |
C36A | 0.84720 (15) | 0.29583 (14) | 0.15658 (8) | 0.0384 (7) | |
H36A | 0.8906 | 0.2865 | 0.1529 | 0.046* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0276 (14) | 0.0241 (13) | 0.0274 (14) | 0.0036 (11) | 0.0063 (12) | −0.0013 (11) |
C11 | 0.0227 (13) | 0.0236 (13) | 0.0292 (14) | 0.0010 (10) | −0.0044 (11) | −0.0004 (11) |
C12 | 0.0222 (13) | 0.0280 (14) | 0.0282 (14) | 0.0006 (11) | −0.0030 (11) | −0.0030 (11) |
O12 | 0.0332 (11) | 0.0281 (10) | 0.0337 (11) | 0.0070 (8) | 0.0062 (9) | 0.0001 (9) |
C13 | 0.0251 (14) | 0.0342 (15) | 0.0303 (14) | 0.0037 (12) | 0.0004 (12) | 0.0060 (12) |
C14 | 0.0283 (14) | 0.0271 (14) | 0.0309 (15) | 0.0024 (11) | −0.0059 (12) | 0.0015 (12) |
C17 | 0.0333 (16) | 0.0367 (17) | 0.0407 (18) | 0.0053 (13) | −0.0102 (13) | −0.0051 (13) |
C18 | 0.0439 (18) | 0.0305 (15) | 0.0400 (17) | 0.0026 (13) | −0.0053 (14) | 0.0079 (13) |
C15 | 0.0354 (15) | 0.0224 (13) | 0.0375 (16) | 0.0045 (11) | −0.0065 (13) | −0.0014 (12) |
C16 | 0.0265 (14) | 0.0277 (14) | 0.0315 (16) | 0.0032 (11) | −0.0048 (12) | 0.0002 (12) |
O16 | 0.0497 (12) | 0.0286 (10) | 0.0309 (11) | 0.0076 (9) | 0.0024 (10) | −0.0022 (9) |
C21 | 0.0283 (14) | 0.0203 (12) | 0.0281 (14) | −0.0001 (11) | 0.0046 (11) | −0.0007 (11) |
C22 | 0.0429 (17) | 0.0222 (13) | 0.0290 (15) | 0.0030 (12) | 0.0052 (13) | 0.0014 (12) |
O22 | 0.0626 (15) | 0.0366 (12) | 0.0273 (11) | 0.0215 (11) | 0.0028 (10) | −0.0032 (9) |
C23 | 0.0530 (19) | 0.0256 (14) | 0.0269 (16) | 0.0046 (13) | −0.0016 (13) | −0.0027 (12) |
C24 | 0.0402 (16) | 0.0225 (13) | 0.0263 (13) | 0.0017 (12) | 0.0008 (12) | 0.0002 (11) |
C27 | 0.0525 (19) | 0.0317 (16) | 0.0348 (17) | −0.0036 (14) | 0.0057 (14) | 0.0035 (14) |
C28 | 0.0507 (19) | 0.0368 (17) | 0.0355 (17) | 0.0045 (14) | −0.0050 (15) | 0.0044 (14) |
C25 | 0.0287 (15) | 0.0257 (14) | 0.0357 (16) | 0.0031 (11) | 0.0012 (12) | 0.0017 (12) |
C26 | 0.0307 (14) | 0.0175 (12) | 0.0303 (15) | −0.0045 (11) | 0.0039 (12) | 0.0014 (11) |
O26 | 0.0321 (10) | 0.0275 (10) | 0.0268 (10) | 0.0024 (8) | 0.0043 (8) | −0.0024 (8) |
C31 | 0.0227 (13) | 0.0266 (13) | 0.0325 (15) | 0.0006 (11) | 0.0064 (12) | −0.0052 (12) |
C32 | 0.0319 (15) | 0.0306 (15) | 0.0446 (18) | −0.0012 (12) | −0.0040 (13) | −0.0005 (13) |
C33 | 0.0347 (16) | 0.0440 (18) | 0.0479 (19) | −0.0073 (14) | −0.0058 (14) | −0.0058 (15) |
C34 | 0.0348 (17) | 0.0357 (18) | 0.057 (2) | −0.0120 (13) | 0.0047 (15) | −0.0129 (16) |
F34 | 0.0691 (14) | 0.0468 (11) | 0.0804 (16) | −0.0305 (10) | −0.0066 (12) | −0.0146 (11) |
C35 | 0.0381 (17) | 0.0274 (15) | 0.061 (2) | −0.0079 (13) | 0.0104 (16) | −0.0002 (15) |
C36 | 0.0316 (15) | 0.0328 (15) | 0.0391 (16) | −0.0040 (12) | 0.0056 (13) | 0.0011 (13) |
C1A | 0.0353 (15) | 0.0300 (15) | 0.0254 (15) | −0.0002 (12) | −0.0058 (12) | 0.0075 (12) |
C11A | 0.0295 (14) | 0.0344 (15) | 0.0252 (14) | −0.0043 (12) | −0.0010 (11) | −0.0004 (12) |
C12A | 0.0210 (13) | 0.0361 (15) | 0.0268 (15) | −0.0056 (11) | −0.0017 (11) | −0.0001 (12) |
O12A | 0.0340 (11) | 0.0346 (11) | 0.0283 (11) | 0.0052 (9) | −0.0019 (9) | 0.0005 (9) |
C13A | 0.0274 (14) | 0.0398 (16) | 0.0364 (16) | 0.0018 (12) | 0.0019 (12) | −0.0037 (13) |
C14A | 0.0353 (16) | 0.0466 (18) | 0.0297 (16) | 0.0018 (13) | 0.0022 (13) | −0.0079 (14) |
C17A | 0.0403 (18) | 0.053 (2) | 0.047 (2) | −0.0081 (15) | −0.0032 (15) | −0.0128 (17) |
C18A | 0.059 (2) | 0.076 (3) | 0.046 (2) | 0.014 (2) | 0.0055 (18) | −0.0233 (19) |
C15A | 0.0432 (18) | 0.063 (2) | 0.0252 (16) | −0.0056 (16) | 0.0017 (13) | −0.0004 (15) |
C16A | 0.0367 (16) | 0.0422 (17) | 0.0309 (16) | −0.0092 (14) | −0.0036 (13) | 0.0056 (14) |
O16A | 0.0660 (15) | 0.0463 (13) | 0.0325 (12) | 0.0012 (11) | −0.0135 (11) | 0.0075 (10) |
C21A | 0.0313 (15) | 0.0263 (14) | 0.0344 (16) | −0.0018 (11) | −0.0039 (12) | −0.0049 (12) |
C22A | 0.0393 (17) | 0.0351 (17) | 0.049 (2) | −0.0006 (14) | −0.0087 (15) | −0.0070 (15) |
O22A | 0.0513 (15) | 0.0623 (16) | 0.0506 (16) | 0.0099 (13) | −0.0169 (13) | 0.0067 (13) |
C23A | 0.0340 (17) | 0.053 (2) | 0.073 (3) | 0.0028 (16) | −0.0101 (17) | −0.0198 (19) |
C24A | 0.0304 (16) | 0.0376 (17) | 0.069 (2) | 0.0006 (13) | 0.0038 (16) | −0.0187 (16) |
C27A | 0.0375 (19) | 0.056 (2) | 0.108 (3) | −0.0072 (17) | 0.018 (2) | −0.030 (2) |
C28A | 0.0462 (19) | 0.0402 (18) | 0.073 (2) | 0.0021 (15) | 0.0014 (18) | −0.0227 (18) |
C25A | 0.0384 (17) | 0.0349 (17) | 0.067 (2) | −0.0060 (14) | 0.0149 (16) | −0.0079 (16) |
C26A | 0.0353 (16) | 0.0227 (13) | 0.0368 (17) | −0.0040 (12) | 0.0032 (13) | −0.0080 (12) |
O26A | 0.0404 (12) | 0.0319 (11) | 0.0336 (11) | 0.0009 (9) | 0.0031 (9) | 0.0034 (9) |
C31A | 0.0352 (15) | 0.0270 (14) | 0.0283 (14) | −0.0086 (12) | −0.0044 (12) | 0.0066 (12) |
C32A | 0.0375 (17) | 0.0306 (15) | 0.0387 (17) | −0.0057 (12) | −0.0020 (13) | 0.0037 (13) |
C33A | 0.0344 (16) | 0.0385 (17) | 0.048 (2) | −0.0100 (13) | −0.0061 (14) | 0.0088 (15) |
C34A | 0.0436 (19) | 0.0478 (19) | 0.0414 (18) | −0.0250 (15) | −0.0112 (15) | 0.0102 (16) |
F34A | 0.0572 (13) | 0.0775 (15) | 0.0517 (12) | −0.0368 (11) | −0.0160 (10) | 0.0004 (11) |
C35A | 0.054 (2) | 0.0487 (19) | 0.0315 (17) | −0.0237 (16) | 0.0051 (15) | −0.0050 (15) |
C36A | 0.0383 (16) | 0.0408 (17) | 0.0362 (16) | −0.0146 (13) | 0.0025 (14) | −0.0009 (14) |
Geometric parameters (Å, º) top
C1—C21 | 1.532 (4) | C1A—C21A | 1.527 (4) |
C1—C11 | 1.535 (4) | C1A—C11A | 1.529 (4) |
C1—C31 | 1.540 (4) | C1A—C31A | 1.537 (4) |
C1—H1 | 1.0000 | C1A—H1A | 1.0000 |
C11—C12 | 1.381 (4) | C11A—C12A | 1.368 (4) |
C11—C16 | 1.436 (4) | C11A—C16A | 1.452 (4) |
C12—O12 | 1.322 (3) | C12A—O12A | 1.332 (3) |
C12—C13 | 1.494 (4) | C12A—C13A | 1.509 (4) |
O12—H12 | 0.95 (4) | O12A—H12A | 0.85 (4) |
C13—C14 | 1.536 (4) | C13A—C14A | 1.536 (4) |
C13—H13A | 0.9900 | C13A—H13C | 0.9900 |
C13—H13B | 0.9900 | C13A—H13D | 0.9900 |
C14—C15 | 1.529 (4) | C14A—C15A | 1.521 (5) |
C14—C17 | 1.532 (4) | C14A—C18A | 1.534 (4) |
C14—C18 | 1.536 (4) | C14A—C17A | 1.540 (4) |
C17—H17A | 0.9800 | C17A—H17D | 0.9800 |
C17—H17B | 0.9800 | C17A—H17E | 0.9800 |
C17—H17C | 0.9800 | C17A—H17F | 0.9800 |
C18—H18A | 0.9800 | C18A—H18D | 0.9800 |
C18—H18B | 0.9800 | C18A—H18E | 0.9800 |
C18—H18C | 0.9800 | C18A—H18F | 0.9800 |
C15—C16 | 1.512 (4) | C15A—C16A | 1.507 (5) |
C15—H15A | 0.9900 | C15A—H15C | 0.9900 |
C15—H15B | 0.9900 | C15A—H15D | 0.9900 |
C16—O16 | 1.267 (3) | C16A—O16A | 1.251 (4) |
C21—C22 | 1.379 (4) | C21A—C22A | 1.366 (4) |
C21—C26 | 1.431 (4) | C21A—C26A | 1.451 (4) |
C22—O22 | 1.323 (3) | C22A—O22A | 1.333 (4) |
C22—C23 | 1.504 (4) | C22A—C23A | 1.498 (5) |
O22—H22 | 0.85 (4) | O22A—H22A | 0.86 (5) |
C23—C24 | 1.532 (4) | C23A—C24A | 1.528 (5) |
C23—H23B | 0.9900 | C23A—H23C | 0.9900 |
C23—H23A | 0.9900 | C23A—H23D | 0.9900 |
C24—C27 | 1.533 (4) | C24A—C25A | 1.532 (5) |
C24—C25 | 1.534 (4) | C24A—C28A | 1.535 (4) |
C24—C28 | 1.534 (4) | C24A—C27A | 1.542 (4) |
C27—H27A | 0.9800 | C27A—H27D | 0.9800 |
C27—H27B | 0.9800 | C27A—H27E | 0.9800 |
C27—H27C | 0.9800 | C27A—H27F | 0.9800 |
C28—H28A | 0.9800 | C28A—H28D | 0.9800 |
C28—H28B | 0.9800 | C28A—H28E | 0.9800 |
C28—H28C | 0.9800 | C28A—H28F | 0.9800 |
C25—C26 | 1.506 (4) | C25A—C26A | 1.508 (4) |
C25—H25A | 0.9900 | C25A—H25C | 0.9900 |
C25—H25B | 0.9900 | C25A—H25D | 0.9900 |
C26—O26 | 1.268 (3) | C26A—O26A | 1.248 (3) |
C31—C36 | 1.393 (4) | C31A—C32A | 1.395 (4) |
C31—C32 | 1.395 (4) | C31A—C36A | 1.394 (4) |
C32—C33 | 1.393 (4) | C32A—C33A | 1.387 (4) |
C32—H32 | 0.9500 | C32A—H32A | 0.9500 |
C33—C34 | 1.371 (5) | C33A—C34A | 1.367 (5) |
C33—H33 | 0.9500 | C33A—H33A | 0.9500 |
C34—C35 | 1.358 (5) | C34A—F34A | 1.367 (3) |
C34—F34 | 1.370 (3) | C34A—C35A | 1.383 (5) |
C35—C36 | 1.389 (4) | C35A—C36A | 1.392 (4) |
C35—H35 | 0.9500 | C35A—H35A | 0.9500 |
C36—H36 | 0.9500 | C36A—H36A | 0.9500 |
| | | |
C21—C1—C11 | 113.5 (2) | C21A—C1A—C11A | 113.2 (2) |
C21—C1—C31 | 113.7 (2) | C21A—C1A—C31A | 114.6 (2) |
C11—C1—C31 | 114.7 (2) | C11A—C1A—C31A | 114.7 (2) |
C21—C1—H1 | 104.5 | C21A—C1A—H1A | 104.2 |
C11—C1—H1 | 104.5 | C11A—C1A—H1A | 104.2 |
C31—C1—H1 | 104.5 | C31A—C1A—H1A | 104.2 |
C12—C11—C16 | 118.2 (2) | C12A—C11A—C16A | 117.9 (3) |
C12—C11—C1 | 124.5 (2) | C12A—C11A—C1A | 125.5 (2) |
C16—C11—C1 | 117.3 (2) | C16A—C11A—C1A | 116.6 (2) |
O12—C12—C11 | 123.2 (2) | O12A—C12A—C11A | 124.1 (3) |
O12—C12—C13 | 113.2 (2) | O12A—C12A—C13A | 111.8 (2) |
C11—C12—C13 | 123.6 (2) | C11A—C12A—C13A | 124.1 (3) |
C12—O12—H12 | 107 (3) | C12A—O12A—H12A | 114 (2) |
C12—C13—C14 | 114.7 (2) | C12A—C13A—C14A | 113.6 (2) |
C12—C13—H13A | 108.6 | C12A—C13A—H13C | 108.8 |
C14—C13—H13A | 108.6 | C14A—C13A—H13C | 108.8 |
C12—C13—H13B | 108.6 | C12A—C13A—H13D | 108.8 |
C14—C13—H13B | 108.6 | C14A—C13A—H13D | 108.8 |
H13A—C13—H13B | 107.6 | H13C—C13A—H13D | 107.7 |
C15—C14—C17 | 110.9 (2) | C15A—C14A—C18A | 111.4 (3) |
C15—C14—C13 | 108.2 (2) | C15A—C14A—C13A | 107.3 (2) |
C17—C14—C13 | 109.9 (2) | C18A—C14A—C13A | 109.2 (3) |
C15—C14—C18 | 108.7 (2) | C15A—C14A—C17A | 109.6 (3) |
C17—C14—C18 | 109.6 (2) | C18A—C14A—C17A | 108.5 (3) |
C13—C14—C18 | 109.4 (2) | C13A—C14A—C17A | 111.0 (3) |
C14—C17—H17A | 109.5 | C14A—C17A—H17D | 109.5 |
C14—C17—H17B | 109.5 | C14A—C17A—H17E | 109.5 |
H17A—C17—H17B | 109.5 | H17D—C17A—H17E | 109.5 |
C14—C17—H17C | 109.5 | C14A—C17A—H17F | 109.5 |
H17A—C17—H17C | 109.5 | H17D—C17A—H17F | 109.5 |
H17B—C17—H17C | 109.5 | H17E—C17A—H17F | 109.5 |
C14—C18—H18A | 109.5 | C14A—C18A—H18D | 109.5 |
C14—C18—H18B | 109.5 | C14A—C18A—H18E | 109.5 |
H18A—C18—H18B | 109.5 | H18D—C18A—H18E | 109.5 |
C14—C18—H18C | 109.5 | C14A—C18A—H18F | 109.5 |
H18A—C18—H18C | 109.5 | H18D—C18A—H18F | 109.5 |
H18B—C18—H18C | 109.5 | H18E—C18A—H18F | 109.5 |
C16—C15—C14 | 115.6 (2) | C16A—C15A—C14A | 112.0 (2) |
C16—C15—H15A | 108.4 | C16A—C15A—H15C | 109.2 |
C14—C15—H15A | 108.4 | C14A—C15A—H15C | 109.2 |
C16—C15—H15B | 108.4 | C16A—C15A—H15D | 109.2 |
C14—C15—H15B | 108.4 | C14A—C15A—H15D | 109.2 |
H15A—C15—H15B | 107.4 | H15C—C15A—H15D | 107.9 |
O16—C16—C11 | 122.4 (2) | O16A—C16A—C11A | 121.5 (3) |
O16—C16—C15 | 117.1 (2) | O16A—C16A—C15A | 120.1 (3) |
C11—C16—C15 | 120.4 (2) | C11A—C16A—C15A | 118.4 (3) |
C22—C21—C26 | 117.8 (3) | C22A—C21A—C26A | 118.1 (3) |
C22—C21—C1 | 121.1 (2) | C22A—C21A—C1A | 121.2 (3) |
C26—C21—C1 | 121.0 (2) | C26A—C21A—C1A | 120.5 (2) |
O22—C22—C21 | 123.6 (3) | O22A—C22A—C21A | 123.7 (3) |
O22—C22—C23 | 113.4 (2) | O22A—C22A—C23A | 112.3 (3) |
C21—C22—C23 | 123.0 (2) | C21A—C22A—C23A | 124.0 (3) |
C22—O22—H22 | 113 (3) | C22A—O22A—H22A | 114 (3) |
C22—C23—C24 | 114.0 (2) | C22A—C23A—C24A | 114.7 (3) |
C22—C23—H23B | 108.8 | C22A—C23A—H23C | 108.6 |
C24—C23—H23B | 108.8 | C24A—C23A—H23C | 108.6 |
C22—C23—H23A | 108.8 | C22A—C23A—H23D | 108.6 |
C24—C23—H23A | 108.8 | C24A—C23A—H23D | 108.6 |
H23B—C23—H23A | 107.7 | H23C—C23A—H23D | 107.6 |
C23—C24—C27 | 111.1 (2) | C23A—C24A—C25A | 108.1 (3) |
C23—C24—C25 | 107.1 (2) | C23A—C24A—C28A | 110.6 (3) |
C27—C24—C25 | 111.1 (2) | C25A—C24A—C28A | 109.8 (3) |
C23—C24—C28 | 109.0 (2) | C23A—C24A—C27A | 110.0 (3) |
C27—C24—C28 | 109.0 (2) | C25A—C24A—C27A | 109.6 (3) |
C25—C24—C28 | 109.6 (2) | C28A—C24A—C27A | 108.8 (3) |
C24—C27—H27A | 109.5 | C24A—C27A—H27D | 109.5 |
C24—C27—H27B | 109.5 | C24A—C27A—H27E | 109.5 |
H27A—C27—H27B | 109.5 | H27D—C27A—H27E | 109.5 |
C24—C27—H27C | 109.5 | C24A—C27A—H27F | 109.5 |
H27A—C27—H27C | 109.5 | H27D—C27A—H27F | 109.5 |
H27B—C27—H27C | 109.5 | H27E—C27A—H27F | 109.5 |
C24—C28—H28A | 109.5 | C24A—C28A—H28D | 109.5 |
C24—C28—H28B | 109.5 | C24A—C28A—H28E | 109.5 |
H28A—C28—H28B | 109.5 | H28D—C28A—H28E | 109.5 |
C24—C28—H28C | 109.5 | C24A—C28A—H28F | 109.5 |
H28A—C28—H28C | 109.5 | H28D—C28A—H28F | 109.5 |
H28B—C28—H28C | 109.5 | H28E—C28A—H28F | 109.5 |
C26—C25—C24 | 115.1 (2) | C26A—C25A—C24A | 114.5 (3) |
C26—C25—H25A | 108.5 | C26A—C25A—H25C | 108.6 |
C24—C25—H25A | 108.5 | C24A—C25A—H25C | 108.6 |
C26—C25—H25B | 108.5 | C26A—C25A—H25D | 108.6 |
C24—C25—H25B | 108.5 | C24A—C25A—H25D | 108.6 |
H25A—C25—H25B | 107.5 | H25C—C25A—H25D | 107.6 |
O26—C26—C21 | 122.4 (2) | O26A—C26A—C21A | 122.0 (3) |
O26—C26—C25 | 117.0 (2) | O26A—C26A—C25A | 118.3 (3) |
C21—C26—C25 | 120.6 (2) | C21A—C26A—C25A | 119.6 (3) |
C36—C31—C32 | 117.9 (3) | C32A—C31A—C36A | 117.6 (3) |
C36—C31—C1 | 120.6 (3) | C32A—C31A—C1A | 121.5 (3) |
C32—C31—C1 | 121.2 (2) | C36A—C31A—C1A | 120.6 (3) |
C33—C32—C31 | 121.2 (3) | C33A—C32A—C31A | 121.8 (3) |
C33—C32—H32 | 119.4 | C33A—C32A—H32A | 119.1 |
C31—C32—H32 | 119.4 | C31A—C32A—H32A | 119.1 |
C34—C33—C32 | 118.1 (3) | C34A—C33A—C32A | 118.5 (3) |
C34—C33—H33 | 120.9 | C34A—C33A—H33A | 120.8 |
C32—C33—H33 | 120.9 | C32A—C33A—H33A | 120.8 |
C35—C34—F34 | 119.0 (3) | F34A—C34A—C33A | 119.5 (3) |
C35—C34—C33 | 122.8 (3) | F34A—C34A—C35A | 118.0 (3) |
F34—C34—C33 | 118.2 (3) | C33A—C34A—C35A | 122.5 (3) |
C34—C35—C36 | 118.7 (3) | C34A—C35A—C36A | 118.0 (3) |
C34—C35—H35 | 120.7 | C34A—C35A—H35A | 121.0 |
C36—C35—H35 | 120.7 | C36A—C35A—H35A | 121.0 |
C35—C36—C31 | 121.2 (3) | C35A—C36A—C31A | 121.6 (3) |
C35—C36—H36 | 119.4 | C35A—C36A—H36A | 119.2 |
C31—C36—H36 | 119.4 | C31A—C36A—H36A | 119.2 |
| | | |
C21—C1—C11—C12 | −85.9 (3) | C21A—C1A—C11A—C12A | 83.0 (3) |
C31—C1—C11—C12 | 47.1 (3) | C31A—C1A—C11A—C12A | −51.0 (4) |
C21—C1—C11—C16 | 91.1 (3) | C21A—C1A—C11A—C16A | −95.1 (3) |
C31—C1—C11—C16 | −135.9 (2) | C31A—C1A—C11A—C16A | 130.8 (3) |
C16—C11—C12—O12 | −172.1 (2) | C16A—C11A—C12A—O12A | 176.9 (2) |
C1—C11—C12—O12 | 4.9 (4) | C1A—C11A—C12A—O12A | −1.2 (4) |
C16—C11—C12—C13 | 6.9 (4) | C16A—C11A—C12A—C13A | −3.8 (4) |
C1—C11—C12—C13 | −176.2 (2) | C1A—C11A—C12A—C13A | 178.1 (3) |
O12—C12—C13—C14 | −159.6 (2) | O12A—C12A—C13A—C14A | −159.0 (2) |
C11—C12—C13—C14 | 21.3 (4) | C11A—C12A—C13A—C14A | 21.6 (4) |
C12—C13—C14—C15 | −46.1 (3) | C12A—C13A—C14A—C15A | −47.0 (3) |
C12—C13—C14—C17 | 75.1 (3) | C12A—C13A—C14A—C18A | −167.8 (3) |
C12—C13—C14—C18 | −164.4 (2) | C12A—C13A—C14A—C17A | 72.7 (3) |
C17—C14—C15—C16 | −74.0 (3) | C18A—C14A—C15A—C16A | 177.2 (3) |
C13—C14—C15—C16 | 46.6 (3) | C13A—C14A—C15A—C16A | 57.8 (3) |
C18—C14—C15—C16 | 165.4 (2) | C17A—C14A—C15A—C16A | −62.8 (3) |
C12—C11—C16—O16 | 169.7 (3) | C12A—C11A—C16A—O16A | −165.5 (3) |
C1—C11—C16—O16 | −7.5 (4) | C1A—C11A—C16A—O16A | 12.8 (4) |
C12—C11—C16—C15 | −6.6 (4) | C12A—C11A—C16A—C15A | 14.6 (4) |
C1—C11—C16—C15 | 176.2 (2) | C1A—C11A—C16A—C15A | −167.0 (2) |
C14—C15—C16—O16 | 161.5 (2) | C14A—C15A—C16A—O16A | 136.7 (3) |
C14—C15—C16—C11 | −22.0 (4) | C14A—C15A—C16A—C11A | −43.5 (4) |
C11—C1—C21—C22 | −92.0 (3) | C11A—C1A—C21A—C22A | 94.2 (3) |
C31—C1—C21—C22 | 134.5 (3) | C31A—C1A—C21A—C22A | −131.7 (3) |
C11—C1—C21—C26 | 83.9 (3) | C11A—C1A—C21A—C26A | −81.3 (3) |
C31—C1—C21—C26 | −49.5 (3) | C31A—C1A—C21A—C26A | 52.8 (3) |
C26—C21—C22—O22 | −169.4 (3) | C26A—C21A—C22A—O22A | 169.5 (3) |
C1—C21—C22—O22 | 6.6 (4) | C1A—C21A—C22A—O22A | −6.0 (5) |
C26—C21—C22—C23 | 9.4 (4) | C26A—C21A—C22A—C23A | −10.9 (4) |
C1—C21—C22—C23 | −174.5 (2) | C1A—C21A—C22A—C23A | 173.6 (3) |
O22—C22—C23—C24 | −158.7 (2) | O22A—C22A—C23A—C24A | 163.9 (3) |
C21—C22—C23—C24 | 22.4 (4) | C21A—C22A—C23A—C24A | −15.7 (5) |
C22—C23—C24—C27 | 72.1 (3) | C22A—C23A—C24A—C25A | 44.8 (4) |
C22—C23—C24—C25 | −49.3 (3) | C22A—C23A—C24A—C28A | −75.5 (4) |
C22—C23—C24—C28 | −167.8 (3) | C22A—C23A—C24A—C27A | 164.4 (3) |
C23—C24—C25—C26 | 49.0 (3) | C23A—C24A—C25A—C26A | −50.5 (4) |
C27—C24—C25—C26 | −72.4 (3) | C28A—C24A—C25A—C26A | 70.3 (4) |
C28—C24—C25—C26 | 167.1 (2) | C27A—C24A—C25A—C26A | −170.3 (3) |
C22—C21—C26—O26 | 168.1 (2) | C22A—C21A—C26A—O26A | −172.7 (3) |
C1—C21—C26—O26 | −8.0 (4) | C1A—C21A—C26A—O26A | 2.9 (4) |
C22—C21—C26—C25 | −10.1 (4) | C22A—C21A—C26A—C25A | 4.7 (4) |
C1—C21—C26—C25 | 173.8 (2) | C1A—C21A—C26A—C25A | −179.7 (3) |
C24—C25—C26—O26 | 160.7 (2) | C24A—C25A—C26A—O26A | −155.0 (3) |
C24—C25—C26—C21 | −21.1 (3) | C24A—C25A—C26A—C21A | 27.5 (4) |
C21—C1—C31—C36 | −29.0 (3) | C21A—C1A—C31A—C32A | −158.2 (3) |
C11—C1—C31—C36 | −162.0 (2) | C11A—C1A—C31A—C32A | −24.8 (4) |
C21—C1—C31—C32 | 156.8 (2) | C21A—C1A—C31A—C36A | 29.0 (4) |
C11—C1—C31—C32 | 23.9 (3) | C11A—C1A—C31A—C36A | 162.4 (3) |
C36—C31—C32—C33 | 1.7 (4) | C36A—C31A—C32A—C33A | −2.4 (4) |
C1—C31—C32—C33 | 176.0 (3) | C1A—C31A—C32A—C33A | −175.5 (3) |
C31—C32—C33—C34 | −0.8 (5) | C31A—C32A—C33A—C34A | 0.0 (4) |
C32—C33—C34—C35 | −0.4 (5) | C32A—C33A—C34A—F34A | −177.4 (3) |
C32—C33—C34—F34 | −179.5 (3) | C32A—C33A—C34A—C35A | 2.5 (5) |
F34—C34—C35—C36 | 179.6 (3) | F34A—C34A—C35A—C36A | 177.6 (3) |
C33—C34—C35—C36 | 0.5 (5) | C33A—C34A—C35A—C36A | −2.3 (5) |
C34—C35—C36—C31 | 0.6 (4) | C34A—C35A—C36A—C31A | −0.3 (5) |
C32—C31—C36—C35 | −1.7 (4) | C32A—C31A—C36A—C35A | 2.6 (4) |
C1—C31—C36—C35 | −176.0 (3) | C1A—C31A—C36A—C35A | 175.7 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O12—H12···O26 | 0.95 (4) | 1.68 (4) | 2.590 (3) | 161 (4) |
O22—H22···O16 | 0.85 (4) | 1.81 (4) | 2.636 (3) | 164 (4) |
O12A—H12A···O26A | 0.85 (4) | 1.77 (4) | 2.564 (3) | 154 (3) |
O22A—H22A···O16A | 0.86 (5) | 1.85 (5) | 2.701 (4) | 174 (5) |
Crystal data top
C23H27ClO4 | F(000) = 856 |
Mr = 402.90 | Dx = 1.265 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.892 (1) Å | Cell parameters from 4736 reflections |
b = 11.813 (1) Å | θ = 0–25° |
c = 13.351 (1) Å | µ = 0.21 mm−1 |
β = 115.78 (1)° | T = 173 K |
V = 2114.9 (3) Å3 | Block, colourless |
Z = 4 | 0.54 × 0.42 × 0.36 mm |
Data collection top
Siemens CCD three-circle diffractometer | 4667 independent reflections |
Radiation source: fine-focus sealed tube | 3419 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
ω scans | θmax = 27.1°, θmin = 1.5° |
Absorption correction: empirical (SADABS; Sheldrick, 1996) | h = −19→19 |
Tmin = 0.897, Tmax = 0.930 | k = −15→15 |
39320 measured reflections | l = −17→17 |
Refinement top
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)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0442P)2 + 0.8901P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
4667 reflections | Δρmax = 0.28 e Å−3 |
262 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0041 (8) |
Special details top
Experimental. ; |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 >
σ(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.22157 (12) | 0.49071 (13) | 0.51543 (13) | 0.0224 (3) | |
H1 | 0.1695 | 0.4734 | 0.4388 | 0.027* | |
C11 | 0.22324 (12) | 0.62002 (13) | 0.52160 (13) | 0.0224 (3) | |
C12 | 0.18504 (12) | 0.68418 (14) | 0.42466 (13) | 0.0235 (3) | |
O12 | 0.15613 (9) | 0.63941 (10) | 0.32547 (9) | 0.0304 (3) | |
H12 | 0.194 (2) | 0.560 (3) | 0.326 (2) | 0.104 (10)* | |
C13 | 0.17651 (13) | 0.81076 (14) | 0.42427 (13) | 0.0270 (4) | |
H13A | 0.1139 | 0.8336 | 0.3603 | 0.032* | |
H13B | 0.2326 | 0.8441 | 0.4133 | 0.032* | |
C14 | 0.17719 (13) | 0.86003 (14) | 0.53093 (14) | 0.0266 (4) | |
C17 | 0.19335 (16) | 0.98841 (15) | 0.53394 (16) | 0.0394 (5) | |
H17A | 0.2553 | 1.0046 | 0.5277 | 0.059* | |
H17B | 0.1979 | 1.0189 | 0.6043 | 0.059* | |
H17C | 0.1372 | 1.0238 | 0.4717 | 0.059* | |
C18 | 0.07702 (13) | 0.83623 (16) | 0.53462 (15) | 0.0349 (4) | |
H18A | 0.0234 | 0.8760 | 0.4732 | 0.052* | |
H18B | 0.0801 | 0.8629 | 0.6056 | 0.052* | |
H18C | 0.0638 | 0.7547 | 0.5274 | 0.052* | |
C15 | 0.26382 (12) | 0.80542 (14) | 0.63046 (13) | 0.0264 (4) | |
H15A | 0.3270 | 0.8391 | 0.6371 | 0.032* | |
H15B | 0.2570 | 0.8249 | 0.6989 | 0.032* | |
C16 | 0.27113 (12) | 0.67821 (14) | 0.62462 (13) | 0.0246 (4) | |
O16 | 0.32404 (9) | 0.62723 (11) | 0.71576 (9) | 0.0346 (3) | |
C21 | 0.31697 (12) | 0.43707 (13) | 0.51963 (13) | 0.0235 (3) | |
C22 | 0.39823 (13) | 0.40510 (14) | 0.61727 (14) | 0.0275 (4) | |
O22 | 0.40875 (9) | 0.43445 (11) | 0.71632 (9) | 0.0352 (3) | |
H22 | 0.364 (3) | 0.516 (3) | 0.717 (3) | 0.139 (13)* | |
C23 | 0.48186 (13) | 0.33348 (15) | 0.61733 (15) | 0.0319 (4) | |
H23A | 0.5002 | 0.2766 | 0.6775 | 0.038* | |
H23B | 0.5407 | 0.3825 | 0.6350 | 0.038* | |
C24 | 0.45819 (13) | 0.27141 (15) | 0.50743 (15) | 0.0302 (4) | |
C27 | 0.55474 (14) | 0.22635 (18) | 0.50696 (18) | 0.0430 (5) | |
H27A | 0.5391 | 0.1881 | 0.4361 | 0.065* | |
H27B | 0.5865 | 0.1726 | 0.5683 | 0.065* | |
H27C | 0.6003 | 0.2896 | 0.5162 | 0.065* | |
C28 | 0.38791 (14) | 0.17100 (16) | 0.49155 (17) | 0.0376 (4) | |
H28A | 0.3742 | 0.1329 | 0.4212 | 0.056* | |
H28B | 0.3253 | 0.1984 | 0.4901 | 0.056* | |
H28C | 0.4194 | 0.1176 | 0.5532 | 0.056* | |
C25 | 0.41011 (13) | 0.35758 (15) | 0.41333 (15) | 0.0310 (4) | |
H25A | 0.4617 | 0.4120 | 0.4162 | 0.037* | |
H25B | 0.3855 | 0.3173 | 0.3412 | 0.037* | |
C26 | 0.32482 (12) | 0.42247 (14) | 0.41790 (14) | 0.0256 (4) | |
O26 | 0.26248 (9) | 0.46616 (10) | 0.32641 (9) | 0.0298 (3) | |
C31 | 0.18285 (12) | 0.43268 (14) | 0.59301 (13) | 0.0235 (3) | |
C32 | 0.12458 (13) | 0.48992 (15) | 0.63529 (15) | 0.0305 (4) | |
H32 | 0.1088 | 0.5674 | 0.6170 | 0.037* | |
C33 | 0.08902 (13) | 0.43551 (15) | 0.70403 (15) | 0.0316 (4) | |
H33 | 0.0497 | 0.4755 | 0.7324 | 0.038* | |
C34 | 0.11200 (12) | 0.32298 (15) | 0.73000 (13) | 0.0263 (4) | |
Cl1 | 0.07554 (3) | 0.25460 (4) | 0.82338 (4) | 0.03448 (13) | |
C35 | 0.16520 (12) | 0.26240 (14) | 0.68544 (13) | 0.0275 (4) | |
H35 | 0.1781 | 0.1841 | 0.7013 | 0.033* | |
C36 | 0.19970 (13) | 0.31769 (14) | 0.61680 (13) | 0.0269 (4) | |
H36 | 0.2357 | 0.2759 | 0.5854 | 0.032* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0255 (8) | 0.0222 (8) | 0.0190 (8) | −0.0005 (7) | 0.0091 (7) | −0.0004 (6) |
C11 | 0.0240 (8) | 0.0220 (8) | 0.0228 (8) | 0.0009 (7) | 0.0118 (7) | 0.0003 (6) |
C12 | 0.0242 (8) | 0.0257 (9) | 0.0239 (8) | 0.0021 (7) | 0.0137 (7) | 0.0005 (7) |
O12 | 0.0402 (7) | 0.0300 (7) | 0.0205 (6) | 0.0095 (6) | 0.0126 (5) | 0.0012 (5) |
C13 | 0.0327 (9) | 0.0253 (9) | 0.0262 (8) | 0.0037 (7) | 0.0157 (7) | 0.0031 (7) |
C14 | 0.0312 (9) | 0.0232 (9) | 0.0281 (9) | 0.0013 (7) | 0.0154 (7) | −0.0007 (7) |
C17 | 0.0530 (12) | 0.0251 (10) | 0.0410 (11) | 0.0008 (9) | 0.0212 (10) | −0.0026 (8) |
C18 | 0.0337 (10) | 0.0403 (11) | 0.0351 (10) | 0.0058 (8) | 0.0191 (8) | 0.0003 (8) |
C15 | 0.0285 (9) | 0.0242 (9) | 0.0269 (8) | −0.0015 (7) | 0.0123 (7) | −0.0048 (7) |
C16 | 0.0255 (9) | 0.0263 (9) | 0.0238 (8) | −0.0009 (7) | 0.0125 (7) | 0.0005 (7) |
O16 | 0.0397 (7) | 0.0330 (7) | 0.0225 (6) | 0.0030 (6) | 0.0056 (5) | 0.0021 (5) |
C21 | 0.0256 (8) | 0.0206 (8) | 0.0243 (8) | −0.0016 (7) | 0.0108 (7) | −0.0005 (6) |
C22 | 0.0277 (9) | 0.0242 (9) | 0.0299 (9) | −0.0023 (7) | 0.0119 (7) | 0.0018 (7) |
O22 | 0.0398 (7) | 0.0379 (7) | 0.0237 (6) | 0.0036 (6) | 0.0098 (5) | −0.0001 (5) |
C23 | 0.0270 (9) | 0.0308 (9) | 0.0355 (10) | 0.0020 (7) | 0.0113 (8) | 0.0059 (8) |
C24 | 0.0286 (9) | 0.0284 (10) | 0.0382 (10) | 0.0031 (7) | 0.0187 (8) | 0.0038 (8) |
C27 | 0.0361 (11) | 0.0459 (12) | 0.0546 (13) | 0.0123 (9) | 0.0268 (10) | 0.0110 (10) |
C28 | 0.0406 (11) | 0.0293 (10) | 0.0501 (12) | −0.0009 (8) | 0.0264 (10) | −0.0006 (9) |
C25 | 0.0357 (10) | 0.0289 (9) | 0.0351 (10) | 0.0037 (8) | 0.0217 (8) | 0.0037 (8) |
C26 | 0.0288 (9) | 0.0198 (8) | 0.0297 (9) | −0.0025 (7) | 0.0141 (7) | 0.0007 (7) |
O26 | 0.0398 (7) | 0.0268 (6) | 0.0237 (6) | 0.0062 (5) | 0.0146 (5) | 0.0008 (5) |
C31 | 0.0249 (8) | 0.0243 (9) | 0.0213 (8) | −0.0004 (7) | 0.0100 (7) | 0.0002 (6) |
C32 | 0.0357 (10) | 0.0222 (9) | 0.0390 (10) | 0.0048 (7) | 0.0213 (9) | 0.0056 (7) |
C33 | 0.0360 (10) | 0.0289 (9) | 0.0389 (10) | 0.0039 (8) | 0.0248 (8) | 0.0007 (8) |
C34 | 0.0283 (9) | 0.0295 (9) | 0.0231 (8) | −0.0037 (7) | 0.0129 (7) | 0.0018 (7) |
Cl1 | 0.0396 (3) | 0.0374 (3) | 0.0340 (2) | 0.0007 (2) | 0.0231 (2) | 0.00790 (19) |
C35 | 0.0342 (9) | 0.0210 (9) | 0.0292 (9) | 0.0011 (7) | 0.0156 (8) | 0.0030 (7) |
C36 | 0.0330 (9) | 0.0245 (9) | 0.0276 (9) | 0.0026 (7) | 0.0172 (7) | 0.0002 (7) |
Geometric parameters (Å, º) top
C1—C11 | 1.529 (2) | C22—C23 | 1.505 (2) |
C1—C21 | 1.534 (2) | O22—H22 | 1.17 (4) |
C1—C31 | 1.547 (2) | C23—C24 | 1.538 (2) |
C1—H1 | 1.0000 | C23—H23A | 0.9900 |
C11—C12 | 1.390 (2) | C23—H23B | 0.9900 |
C11—C16 | 1.421 (2) | C24—C25 | 1.531 (2) |
C12—O12 | 1.3125 (19) | C24—C28 | 1.534 (2) |
C12—C13 | 1.500 (2) | C24—C27 | 1.536 (2) |
O12—H12 | 1.09 (3) | C27—H27A | 0.9800 |
C13—C14 | 1.534 (2) | C27—H27B | 0.9800 |
C13—H13A | 0.9900 | C27—H27C | 0.9800 |
C13—H13B | 0.9900 | C28—H28A | 0.9800 |
C14—C17 | 1.533 (2) | C28—H28B | 0.9800 |
C14—C15 | 1.535 (2) | C28—H28C | 0.9800 |
C14—C18 | 1.540 (2) | C25—C26 | 1.507 (2) |
C17—H17A | 0.9800 | C25—H25A | 0.9900 |
C17—H17B | 0.9800 | C25—H25B | 0.9900 |
C17—H17C | 0.9800 | C26—O26 | 1.278 (2) |
C18—H18A | 0.9800 | C31—C36 | 1.393 (2) |
C18—H18B | 0.9800 | C31—C32 | 1.398 (2) |
C18—H18C | 0.9800 | C32—C33 | 1.399 (2) |
C15—C16 | 1.511 (2) | C32—H32 | 0.9500 |
C15—H15A | 0.9900 | C33—C34 | 1.379 (2) |
C15—H15B | 0.9900 | C33—H33 | 0.9500 |
C16—O16 | 1.2768 (19) | C34—C35 | 1.380 (2) |
O16—H22 | 1.44 (4) | C34—Cl1 | 1.7579 (16) |
C21—C22 | 1.391 (2) | C35—C36 | 1.393 (2) |
C21—C26 | 1.424 (2) | C35—H35 | 0.9500 |
C22—O22 | 1.309 (2) | C36—H36 | 0.9500 |
| | | |
C11—C1—C21 | 114.68 (13) | C22—O22—H22 | 113.9 (17) |
C11—C1—C31 | 114.11 (13) | C22—C23—C24 | 114.91 (14) |
C21—C1—C31 | 113.66 (13) | C22—C23—H23A | 108.5 |
C11—C1—H1 | 104.3 | C24—C23—H23A | 108.5 |
C21—C1—H1 | 104.3 | C22—C23—H23B | 108.5 |
C31—C1—H1 | 104.3 | C24—C23—H23B | 108.5 |
C12—C11—C16 | 117.85 (15) | H23A—C23—H23B | 107.5 |
C12—C11—C1 | 120.26 (14) | C25—C24—C28 | 110.67 (15) |
C16—C11—C1 | 121.65 (14) | C25—C24—C27 | 109.37 (14) |
O12—C12—C11 | 122.78 (15) | C28—C24—C27 | 108.36 (15) |
O12—C12—C13 | 114.08 (14) | C25—C24—C23 | 107.29 (14) |
C11—C12—C13 | 123.11 (14) | C28—C24—C23 | 111.10 (14) |
C12—O12—H12 | 113.1 (15) | C27—C24—C23 | 110.04 (15) |
C12—C13—C14 | 114.11 (13) | C24—C27—H27A | 109.5 |
C12—C13—H13A | 108.7 | C24—C27—H27B | 109.5 |
C14—C13—H13A | 108.7 | H27A—C27—H27B | 109.5 |
C12—C13—H13B | 108.7 | C24—C27—H27C | 109.5 |
C14—C13—H13B | 108.7 | H27A—C27—H27C | 109.5 |
H13A—C13—H13B | 107.6 | H27B—C27—H27C | 109.5 |
C17—C14—C13 | 109.70 (14) | C24—C28—H28A | 109.5 |
C17—C14—C15 | 109.26 (15) | C24—C28—H28B | 109.5 |
C13—C14—C15 | 107.94 (13) | H28A—C28—H28B | 109.5 |
C17—C14—C18 | 108.84 (15) | C24—C28—H28C | 109.5 |
C13—C14—C18 | 110.18 (14) | H28A—C28—H28C | 109.5 |
C15—C14—C18 | 110.90 (14) | H28B—C28—H28C | 109.5 |
C14—C17—H17A | 109.5 | C26—C25—C24 | 113.98 (14) |
C14—C17—H17B | 109.5 | C26—C25—H25A | 108.8 |
H17A—C17—H17B | 109.5 | C24—C25—H25A | 108.8 |
C14—C17—H17C | 109.5 | C26—C25—H25B | 108.8 |
H17A—C17—H17C | 109.5 | C24—C25—H25B | 108.8 |
H17B—C17—H17C | 109.5 | H25A—C25—H25B | 107.7 |
C14—C18—H18A | 109.5 | O26—C26—C21 | 122.40 (15) |
C14—C18—H18B | 109.5 | O26—C26—C25 | 116.19 (14) |
H18A—C18—H18B | 109.5 | C21—C26—C25 | 121.37 (15) |
C14—C18—H18C | 109.5 | C36—C31—C32 | 117.48 (15) |
H18A—C18—H18C | 109.5 | C36—C31—C1 | 120.14 (14) |
H18B—C18—H18C | 109.5 | C32—C31—C1 | 122.23 (14) |
C16—C15—C14 | 115.19 (14) | C31—C32—C33 | 121.39 (16) |
C16—C15—H15A | 108.5 | C31—C32—H32 | 119.3 |
C14—C15—H15A | 108.5 | C33—C32—H32 | 119.3 |
C16—C15—H15B | 108.5 | C34—C33—C32 | 118.97 (16) |
C14—C15—H15B | 108.5 | C34—C33—H33 | 120.5 |
H15A—C15—H15B | 107.5 | C32—C33—H33 | 120.5 |
O16—C16—C11 | 122.42 (15) | C33—C34—C35 | 121.19 (15) |
O16—C16—C15 | 116.64 (14) | C33—C34—Cl1 | 120.13 (13) |
C11—C16—C15 | 120.92 (14) | C35—C34—Cl1 | 118.67 (13) |
C16—O16—H22 | 121.4 (14) | C34—C35—C36 | 119.06 (16) |
C22—C21—C26 | 117.54 (15) | C34—C35—H35 | 120.5 |
C22—C21—C1 | 124.12 (14) | C36—C35—H35 | 120.5 |
C26—C21—C1 | 118.31 (14) | C35—C36—C31 | 121.74 (15) |
O22—C22—C21 | 123.23 (16) | C35—C36—H36 | 119.1 |
O22—C22—C23 | 114.39 (15) | C31—C36—H36 | 119.1 |
C21—C22—C23 | 122.38 (15) | | |
| | | |
C21—C1—C11—C12 | 93.38 (18) | C1—C21—C22—C23 | 168.27 (15) |
C31—C1—C11—C12 | −133.04 (15) | O22—C22—C23—C24 | 163.84 (15) |
C21—C1—C11—C16 | −80.95 (18) | C21—C22—C23—C24 | −16.2 (2) |
C31—C1—C11—C16 | 52.6 (2) | C22—C23—C24—C25 | 46.98 (19) |
C16—C11—C12—O12 | 167.15 (15) | C22—C23—C24—C28 | −74.11 (19) |
C1—C11—C12—O12 | −7.4 (2) | C22—C23—C24—C27 | 165.88 (15) |
C16—C11—C12—C13 | −10.7 (2) | C28—C24—C25—C26 | 70.82 (19) |
C1—C11—C12—C13 | 174.80 (15) | C27—C24—C25—C26 | −169.87 (16) |
O12—C12—C13—C14 | 161.32 (14) | C23—C24—C25—C26 | −50.54 (19) |
C11—C12—C13—C14 | −20.7 (2) | C22—C21—C26—O26 | −167.85 (15) |
C12—C13—C14—C17 | 166.55 (15) | C1—C21—C26—O26 | 10.0 (2) |
C12—C13—C14—C15 | 47.59 (19) | C22—C21—C26—C25 | 9.9 (2) |
C12—C13—C14—C18 | −73.64 (19) | C1—C21—C26—C25 | −172.30 (14) |
C17—C14—C15—C16 | −166.47 (14) | C24—C25—C26—O26 | −157.81 (15) |
C13—C14—C15—C16 | −47.23 (19) | C24—C25—C26—C21 | 24.3 (2) |
C18—C14—C15—C16 | 73.56 (18) | C11—C1—C31—C36 | −164.24 (15) |
C12—C11—C16—O16 | −166.91 (15) | C21—C1—C31—C36 | −30.2 (2) |
C1—C11—C16—O16 | 7.6 (2) | C11—C1—C31—C32 | 20.3 (2) |
C12—C11—C16—C15 | 11.3 (2) | C21—C1—C31—C32 | 154.34 (15) |
C1—C11—C16—C15 | −174.20 (14) | C36—C31—C32—C33 | 3.5 (3) |
C14—C15—C16—O16 | −162.32 (14) | C1—C31—C32—C33 | 179.05 (16) |
C14—C15—C16—C11 | 19.3 (2) | C31—C32—C33—C34 | −0.2 (3) |
C11—C1—C21—C22 | 89.96 (19) | C32—C33—C34—C35 | −3.0 (3) |
C31—C1—C21—C22 | −43.8 (2) | C32—C33—C34—Cl1 | 175.81 (14) |
C11—C1—C21—C26 | −87.73 (18) | C33—C34—C35—C36 | 2.7 (3) |
C31—C1—C21—C26 | 138.48 (15) | Cl1—C34—C35—C36 | −176.08 (13) |
C26—C21—C22—O22 | 165.88 (15) | C34—C35—C36—C31 | 0.7 (3) |
C1—C21—C22—O22 | −11.8 (3) | C32—C31—C36—C35 | −3.7 (2) |
C26—C21—C22—C23 | −14.0 (2) | C1—C31—C36—C35 | −179.42 (15) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O12—H12···O26 | 1.09 (3) | 1.50 (3) | 2.5845 (16) | 169 (3) |
O22—H22···O16 | 1.17 (4) | 1.44 (4) | 2.6018 (18) | 169 (3) |
Crystal data top
C23H28O5 | F(000) = 824 |
Mr = 384.45 | Dx = 1.281 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.736 (2) Å | Cell parameters from 3615 reflections |
b = 11.370 (3) Å | θ = 0–25° |
c = 18.263 (3) Å | µ = 0.09 mm−1 |
β = 99.54 (1)° | T = 173 K |
V = 1993.7 (7) Å3 | Plate, colourless |
Z = 4 | 0.50 × 0.20 × 0.10 mm |
Data collection top
Siemens CCD three-circle diffractometer | 4076 independent reflections |
Radiation source: fine-focus sealed tube | 1722 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.090 |
ω scans | θmax = 26.4°, θmin = 2.1° |
Absorption correction: empirical (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.957, Tmax = 0.991 | k = −14→12 |
16535 measured reflections | l = −22→22 |
Refinement top
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)] = 0.079 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.226 | w = 1/[σ2(Fo2) + (0.0852P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.22 | (Δ/σ)max = 0.001 |
4076 reflections | Δρmax = 0.32 e Å−3 |
266 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.009 (2) |
Special details top
Experimental. ; |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 >
σ(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.9184 (4) | 0.4382 (3) | 0.73274 (19) | 0.0452 (10) | |
H1 | 0.8937 | 0.3632 | 0.7561 | 0.054* | |
C11 | 1.0160 (4) | 0.4988 (3) | 0.79535 (19) | 0.0463 (10) | |
C12 | 1.0173 (4) | 0.4676 (4) | 0.8689 (2) | 0.0481 (10) | |
O12 | 0.9297 (3) | 0.3920 (3) | 0.89048 (15) | 0.0602 (8) | |
H12 | 0.841 (6) | 0.370 (5) | 0.851 (3) | 0.13 (2)* | |
C13 | 1.1160 (4) | 0.5223 (4) | 0.9314 (2) | 0.0558 (11) | |
H13A | 1.1373 | 0.4643 | 0.9721 | 0.067* | |
H13B | 1.0696 | 0.5903 | 0.9508 | 0.067* | |
C14 | 1.2527 (4) | 0.5638 (4) | 0.9091 (2) | 0.0512 (11) | |
C17 | 1.3337 (5) | 0.6372 (4) | 0.9727 (2) | 0.0655 (13) | |
H17A | 1.4213 | 0.6643 | 0.9588 | 0.098* | |
H17B | 1.3537 | 0.5888 | 1.0176 | 0.098* | |
H17C | 1.2776 | 0.7053 | 0.9823 | 0.098* | |
C18 | 1.3412 (4) | 0.4584 (4) | 0.8939 (2) | 0.0586 (12) | |
H18A | 1.4279 | 0.4862 | 0.8792 | 0.088* | |
H18B | 1.2894 | 0.4107 | 0.8539 | 0.088* | |
H18C | 1.3630 | 0.4105 | 0.9390 | 0.088* | |
C15 | 1.2150 (4) | 0.6407 (3) | 0.8396 (2) | 0.0502 (10) | |
H15A | 1.1843 | 0.7186 | 0.8551 | 0.060* | |
H15B | 1.3002 | 0.6532 | 0.8176 | 0.060* | |
C16 | 1.1035 (4) | 0.5924 (3) | 0.7806 (2) | 0.0460 (10) | |
O16 | 1.0913 (3) | 0.6418 (2) | 0.71696 (14) | 0.0516 (7) | |
C21 | 0.7771 (4) | 0.4986 (3) | 0.7100 (2) | 0.0466 (10) | |
C22 | 0.7518 (4) | 0.5907 (3) | 0.6611 (2) | 0.0448 (10) | |
O22 | 0.8508 (3) | 0.6511 (2) | 0.63541 (14) | 0.0494 (7) | |
H22 | 0.947 (8) | 0.646 (6) | 0.658 (4) | 0.18 (3)* | |
C23 | 0.6063 (4) | 0.6315 (4) | 0.6307 (2) | 0.0500 (10) | |
H23A | 0.5999 | 0.6474 | 0.5769 | 0.060* | |
H23B | 0.5885 | 0.7064 | 0.6552 | 0.060* | |
C24 | 0.4936 (4) | 0.5433 (4) | 0.6417 (2) | 0.0559 (11) | |
C27 | 0.3496 (4) | 0.5988 (4) | 0.6197 (2) | 0.0621 (12) | |
H27A | 0.2778 | 0.5417 | 0.6272 | 0.093* | |
H27B | 0.3364 | 0.6220 | 0.5673 | 0.093* | |
H27C | 0.3422 | 0.6684 | 0.6505 | 0.093* | |
C28 | 0.5010 (5) | 0.4316 (4) | 0.5935 (2) | 0.0686 (13) | |
H28A | 0.4280 | 0.3762 | 0.6019 | 0.103* | |
H28B | 0.5924 | 0.3943 | 0.6072 | 0.103* | |
H28C | 0.4871 | 0.4537 | 0.5409 | 0.103* | |
C25 | 0.5200 (4) | 0.5064 (4) | 0.7225 (2) | 0.0587 (11) | |
H25A | 0.5062 | 0.5749 | 0.7539 | 0.070* | |
H25B | 0.4515 | 0.4453 | 0.7305 | 0.070* | |
C26 | 0.6656 (4) | 0.4586 (4) | 0.7460 (2) | 0.0568 (11) | |
O26 | 0.6842 (3) | 0.3879 (3) | 0.80061 (16) | 0.0675 (9) | |
C31 | 0.9942 (4) | 0.3961 (3) | 0.67046 (19) | 0.0446 (10) | |
C32 | 1.1154 (4) | 0.3284 (3) | 0.6893 (2) | 0.0494 (10) | |
H32 | 1.1518 | 0.3171 | 0.7404 | 0.059* | |
C33 | 1.1841 (4) | 0.2775 (3) | 0.6372 (2) | 0.0488 (10) | |
H33 | 1.2643 | 0.2303 | 0.6524 | 0.059* | |
C34 | 1.1349 (4) | 0.2959 (3) | 0.5616 (2) | 0.0479 (10) | |
O34 | 1.2091 (3) | 0.2491 (2) | 0.51111 (15) | 0.0568 (8) | |
H34 | 1.160 (6) | 0.275 (5) | 0.455 (3) | 0.118 (18)* | |
C35 | 1.0126 (4) | 0.3602 (3) | 0.5412 (2) | 0.0476 (10) | |
H35 | 0.9760 | 0.3710 | 0.4901 | 0.057* | |
C36 | 0.9439 (4) | 0.4085 (3) | 0.5948 (2) | 0.0465 (10) | |
H36 | 0.8602 | 0.4513 | 0.5795 | 0.056* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.045 (2) | 0.053 (3) | 0.036 (2) | −0.0016 (19) | 0.0030 (17) | 0.0063 (18) |
C11 | 0.049 (2) | 0.051 (3) | 0.039 (2) | 0.001 (2) | 0.0056 (18) | −0.0001 (18) |
C12 | 0.051 (2) | 0.051 (3) | 0.043 (2) | 0.004 (2) | 0.0115 (19) | −0.0030 (19) |
O12 | 0.0629 (19) | 0.075 (2) | 0.0432 (16) | −0.0116 (17) | 0.0087 (14) | 0.0075 (15) |
C13 | 0.062 (3) | 0.060 (3) | 0.044 (2) | 0.006 (2) | 0.0023 (19) | −0.004 (2) |
C14 | 0.054 (2) | 0.056 (3) | 0.041 (2) | 0.001 (2) | −0.0017 (18) | −0.0011 (19) |
C17 | 0.068 (3) | 0.069 (3) | 0.053 (3) | 0.002 (2) | −0.009 (2) | −0.007 (2) |
C18 | 0.060 (3) | 0.060 (3) | 0.055 (3) | 0.009 (2) | 0.006 (2) | 0.002 (2) |
C15 | 0.051 (2) | 0.049 (2) | 0.047 (2) | 0.003 (2) | −0.0043 (18) | −0.0013 (19) |
C16 | 0.048 (2) | 0.051 (3) | 0.040 (2) | 0.004 (2) | 0.0070 (18) | −0.0022 (19) |
O16 | 0.0551 (16) | 0.0552 (17) | 0.0429 (16) | −0.0010 (13) | 0.0036 (12) | 0.0035 (13) |
C21 | 0.046 (2) | 0.044 (2) | 0.048 (2) | 0.0019 (19) | 0.0056 (18) | 0.0049 (19) |
C22 | 0.050 (2) | 0.046 (2) | 0.040 (2) | −0.003 (2) | 0.0094 (18) | 0.0020 (18) |
O22 | 0.0519 (17) | 0.0514 (17) | 0.0446 (15) | −0.0032 (14) | 0.0068 (13) | 0.0060 (13) |
C23 | 0.049 (2) | 0.056 (3) | 0.044 (2) | 0.001 (2) | 0.0039 (18) | 0.0037 (19) |
C24 | 0.051 (2) | 0.061 (3) | 0.055 (2) | −0.003 (2) | 0.006 (2) | 0.005 (2) |
C27 | 0.041 (2) | 0.079 (3) | 0.067 (3) | 0.002 (2) | 0.013 (2) | 0.006 (2) |
C28 | 0.073 (3) | 0.069 (3) | 0.063 (3) | −0.005 (3) | 0.008 (2) | 0.000 (2) |
C25 | 0.055 (3) | 0.065 (3) | 0.058 (3) | 0.000 (2) | 0.016 (2) | 0.000 (2) |
C26 | 0.061 (3) | 0.057 (3) | 0.054 (3) | 0.003 (2) | 0.018 (2) | 0.007 (2) |
O26 | 0.0552 (18) | 0.083 (2) | 0.066 (2) | 0.0026 (16) | 0.0157 (15) | 0.0276 (17) |
C31 | 0.046 (2) | 0.048 (2) | 0.038 (2) | −0.0074 (19) | 0.0026 (17) | −0.0017 (17) |
C32 | 0.050 (2) | 0.056 (3) | 0.040 (2) | −0.002 (2) | −0.0001 (18) | 0.0019 (19) |
C33 | 0.051 (2) | 0.053 (3) | 0.042 (2) | 0.002 (2) | 0.0065 (19) | 0.0001 (19) |
C34 | 0.057 (3) | 0.044 (2) | 0.043 (2) | −0.008 (2) | 0.010 (2) | −0.0037 (19) |
O34 | 0.0608 (18) | 0.0631 (19) | 0.0474 (17) | 0.0014 (15) | 0.0118 (14) | −0.0064 (14) |
C35 | 0.053 (2) | 0.051 (3) | 0.039 (2) | −0.004 (2) | 0.0083 (18) | 0.0046 (19) |
C36 | 0.051 (2) | 0.045 (2) | 0.043 (2) | −0.0048 (19) | 0.0054 (18) | −0.0009 (18) |
Geometric parameters (Å, º) top
C1—C11 | 1.525 (5) | O22—H22 | 0.96 (7) |
C1—C21 | 1.532 (5) | C23—C24 | 1.523 (5) |
C1—C31 | 1.531 (5) | C23—H23A | 0.9900 |
C1—H1 | 1.0000 | C23—H23B | 0.9900 |
C11—C12 | 1.388 (5) | C24—C25 | 1.515 (6) |
C11—C16 | 1.417 (5) | C24—C27 | 1.530 (5) |
C12—O12 | 1.316 (5) | C24—C28 | 1.554 (6) |
C12—C13 | 1.500 (5) | C27—H27A | 0.9800 |
O12—H12 | 1.06 (6) | C27—H27B | 0.9800 |
C13—C14 | 1.529 (5) | C27—H27C | 0.9800 |
C13—H13A | 0.9900 | C28—H28A | 0.9800 |
C13—H13B | 0.9900 | C28—H28B | 0.9800 |
C14—C18 | 1.529 (5) | C28—H28C | 0.9800 |
C14—C15 | 1.535 (5) | C25—C26 | 1.512 (6) |
C14—C17 | 1.537 (5) | C25—H25A | 0.9900 |
C17—H17A | 0.9800 | C25—H25B | 0.9900 |
C17—H17B | 0.9800 | C26—O26 | 1.271 (4) |
C17—H17C | 0.9800 | C31—C36 | 1.395 (5) |
C18—H18A | 0.9800 | C31—C32 | 1.404 (5) |
C18—H18B | 0.9800 | C32—C33 | 1.378 (5) |
C18—H18C | 0.9800 | C32—H32 | 0.9500 |
C15—C16 | 1.501 (5) | C33—C34 | 1.400 (5) |
C15—H15A | 0.9900 | C33—H33 | 0.9500 |
C15—H15B | 0.9900 | C34—O34 | 1.369 (4) |
C16—O16 | 1.278 (4) | C34—C35 | 1.394 (5) |
C21—C22 | 1.372 (5) | O34—H34 | 1.09 (6) |
C21—C26 | 1.433 (5) | C35—C36 | 1.387 (5) |
C22—O22 | 1.331 (4) | C35—H35 | 0.9500 |
C22—C23 | 1.507 (5) | C36—H36 | 0.9500 |
| | | |
C11—C1—C21 | 114.9 (3) | C22—C23—C24 | 113.7 (3) |
C11—C1—C31 | 112.4 (3) | C22—C23—H23A | 108.8 |
C21—C1—C31 | 117.4 (3) | C24—C23—H23A | 108.8 |
C11—C1—H1 | 103.3 | C22—C23—H23B | 108.8 |
C21—C1—H1 | 103.3 | C24—C23—H23B | 108.8 |
C31—C1—H1 | 103.3 | H23A—C23—H23B | 107.7 |
C12—C11—C16 | 117.8 (3) | C25—C24—C23 | 107.6 (3) |
C12—C11—C1 | 121.0 (4) | C25—C24—C27 | 111.7 (3) |
C16—C11—C1 | 121.1 (3) | C23—C24—C27 | 110.0 (3) |
O12—C12—C11 | 123.6 (4) | C25—C24—C28 | 108.0 (3) |
O12—C12—C13 | 114.1 (3) | C23—C24—C28 | 111.2 (3) |
C11—C12—C13 | 122.2 (4) | C27—C24—C28 | 108.3 (3) |
C12—O12—H12 | 116 (3) | C24—C27—H27A | 109.5 |
C12—C13—C14 | 113.7 (3) | C24—C27—H27B | 109.5 |
C12—C13—H13A | 108.8 | H27A—C27—H27B | 109.5 |
C14—C13—H13A | 108.8 | C24—C27—H27C | 109.5 |
C12—C13—H13B | 108.8 | H27A—C27—H27C | 109.5 |
C14—C13—H13B | 108.8 | H27B—C27—H27C | 109.5 |
H13A—C13—H13B | 107.7 | C24—C28—H28A | 109.5 |
C18—C14—C13 | 110.3 (3) | C24—C28—H28B | 109.5 |
C18—C14—C15 | 111.2 (3) | H28A—C28—H28B | 109.5 |
C13—C14—C15 | 107.3 (3) | C24—C28—H28C | 109.5 |
C18—C14—C17 | 109.2 (3) | H28A—C28—H28C | 109.5 |
C13—C14—C17 | 109.0 (3) | H28B—C28—H28C | 109.5 |
C15—C14—C17 | 109.8 (3) | C26—C25—C24 | 112.0 (3) |
C14—C17—H17A | 109.5 | C26—C25—H25A | 109.2 |
C14—C17—H17B | 109.5 | C24—C25—H25A | 109.2 |
H17A—C17—H17B | 109.5 | C26—C25—H25B | 109.2 |
C14—C17—H17C | 109.5 | C24—C25—H25B | 109.2 |
H17A—C17—H17C | 109.5 | H25A—C25—H25B | 107.9 |
H17B—C17—H17C | 109.5 | O26—C26—C21 | 122.7 (4) |
C14—C18—H18A | 109.5 | O26—C26—C25 | 117.1 (4) |
C14—C18—H18B | 109.5 | C21—C26—C25 | 120.1 (4) |
H18A—C18—H18B | 109.5 | C36—C31—C32 | 116.2 (3) |
C14—C18—H18C | 109.5 | C36—C31—C1 | 124.8 (3) |
H18A—C18—H18C | 109.5 | C32—C31—C1 | 118.6 (3) |
H18B—C18—H18C | 109.5 | C33—C32—C31 | 123.1 (4) |
C16—C15—C14 | 115.5 (3) | C33—C32—H32 | 118.5 |
C16—C15—H15A | 108.4 | C31—C32—H32 | 118.5 |
C14—C15—H15A | 108.4 | C32—C33—C34 | 119.5 (4) |
C16—C15—H15B | 108.4 | C32—C33—H33 | 120.3 |
C14—C15—H15B | 108.4 | C34—C33—H33 | 120.3 |
H15A—C15—H15B | 107.5 | O34—C34—C35 | 123.2 (3) |
O16—C16—C11 | 122.3 (3) | O34—C34—C33 | 118.2 (4) |
O16—C16—C15 | 116.1 (3) | C35—C34—C33 | 118.6 (4) |
C11—C16—C15 | 121.6 (3) | C34—O34—H34 | 109 (3) |
C22—C21—C26 | 118.2 (4) | C36—C35—C34 | 120.7 (4) |
C22—C21—C1 | 125.1 (3) | C36—C35—H35 | 119.6 |
C26—C21—C1 | 116.6 (3) | C34—C35—H35 | 119.6 |
O22—C22—C21 | 124.1 (3) | C35—C36—C31 | 121.8 (4) |
O22—C22—C23 | 113.8 (3) | C35—C36—H36 | 119.1 |
C21—C22—C23 | 122.1 (4) | C31—C36—H36 | 119.1 |
C22—O22—H22 | 122 (4) | | |
| | | |
C21—C1—C11—C12 | 91.8 (4) | C1—C21—C22—C23 | 168.7 (3) |
C31—C1—C11—C12 | −130.5 (4) | O22—C22—C23—C24 | 163.5 (3) |
C21—C1—C11—C16 | −85.2 (4) | C21—C22—C23—C24 | −15.8 (5) |
C31—C1—C11—C16 | 52.5 (5) | C22—C23—C24—C25 | 49.8 (4) |
C16—C11—C12—O12 | 171.8 (3) | C22—C23—C24—C27 | 171.7 (3) |
C1—C11—C12—O12 | −5.3 (6) | C22—C23—C24—C28 | −68.2 (4) |
C16—C11—C12—C13 | −5.4 (6) | C23—C24—C25—C26 | −55.5 (5) |
C1—C11—C12—C13 | 177.5 (3) | C27—C24—C25—C26 | −176.3 (4) |
O12—C12—C13—C14 | 154.2 (3) | C28—C24—C25—C26 | 64.7 (5) |
C11—C12—C13—C14 | −28.4 (5) | C22—C21—C26—O26 | −168.1 (4) |
C12—C13—C14—C18 | −70.0 (4) | C1—C21—C26—O26 | 8.8 (6) |
C12—C13—C14—C15 | 51.2 (4) | C22—C21—C26—C25 | 8.0 (6) |
C12—C13—C14—C17 | 170.1 (3) | C1—C21—C26—C25 | −175.0 (3) |
C18—C14—C15—C16 | 75.5 (4) | C24—C25—C26—O26 | −155.1 (4) |
C13—C14—C15—C16 | −45.2 (5) | C24—C25—C26—C21 | 28.5 (6) |
C17—C14—C15—C16 | −163.6 (3) | C11—C1—C31—C36 | −136.7 (4) |
C12—C11—C16—O16 | −166.8 (3) | C21—C1—C31—C36 | −0.2 (5) |
C1—C11—C16—O16 | 10.3 (6) | C11—C1—C31—C32 | 50.9 (4) |
C12—C11—C16—C15 | 12.3 (6) | C21—C1—C31—C32 | −172.6 (3) |
C1—C11—C16—C15 | −170.7 (3) | C36—C31—C32—C33 | 1.0 (6) |
C14—C15—C16—O16 | −165.8 (3) | C1—C31—C32—C33 | 174.0 (4) |
C14—C15—C16—C11 | 15.1 (5) | C31—C32—C33—C34 | 1.9 (6) |
C11—C1—C21—C22 | 84.1 (5) | C32—C33—C34—O34 | 176.9 (3) |
C31—C1—C21—C22 | −51.4 (5) | C32—C33—C34—C35 | −3.5 (6) |
C11—C1—C21—C26 | −92.6 (4) | O34—C34—C35—C36 | −178.1 (3) |
C31—C1—C21—C26 | 131.9 (4) | C33—C34—C35—C36 | 2.3 (6) |
C26—C21—C22—O22 | 166.2 (3) | C34—C35—C36—C31 | 0.6 (6) |
C1—C21—C22—O22 | −10.5 (6) | C32—C31—C36—C35 | −2.2 (6) |
C26—C21—C22—C23 | −14.7 (6) | C1—C31—C36—C35 | −174.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O12—H12···O26 | 1.06 (6) | 1.66 (6) | 2.667 (4) | 157 (5) |
O22—H22···O16 | 0.96 (7) | 1.62 (7) | 2.561 (4) | 165 (6) |
O34—H34···O22i | 1.09 (6) | 1.84 (5) | 2.876 (4) | 156 (4) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Crystal data top
C24H30O4 | F(000) = 824 |
Mr = 382.48 | Dx = 1.195 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.339 (1) Å | Cell parameters from 8192 reflections |
b = 11.638 (1) Å | θ = 0–25° |
c = 20.052 (1) Å | µ = 0.08 mm−1 |
β = 102.65 (1)° | T = 173 K |
V = 2126.5 (3) Å3 | Block, colourless |
Z = 4 | 0.70 × 0.45 × 0.30 mm |
Data collection top
Siemens CCD three-circle diffractometer | 4868 independent reflections |
Radiation source: fine-focus sealed tube | 3895 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω scans | θmax = 27.5°, θmin = 2.0° |
Absorption correction: empirical (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.946, Tmax = 0.976 | k = −15→15 |
40291 measured reflections | l = −26→26 |
Refinement top
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)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.111 | w = 1/[σ2(Fo2) + (0.0494P)2 + 0.6993P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
4868 reflections | Δρmax = 0.24 e Å−3 |
263 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0092 (10) |
Special details top
Experimental. ; |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 >
σ(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.60824 (14) | 0.47467 (11) | 0.26351 (6) | 0.0268 (3) | |
H1 | 0.6373 | 0.4011 | 0.2443 | 0.032* | |
C11 | 0.50206 (14) | 0.52913 (11) | 0.20301 (6) | 0.0272 (3) | |
C12 | 0.50253 (15) | 0.50010 (12) | 0.13691 (7) | 0.0338 (3) | |
O12 | 0.60208 (13) | 0.43132 (10) | 0.11881 (5) | 0.0473 (3) | |
H12 | 0.689 (2) | 0.4208 (19) | 0.1560 (11) | 0.075 (6)* | |
C13 | 0.39239 (17) | 0.54470 (14) | 0.07648 (7) | 0.0409 (3) | |
H13A | 0.3718 | 0.4840 | 0.0411 | 0.049* | |
H13B | 0.4356 | 0.6109 | 0.0569 | 0.049* | |
C14 | 0.24776 (15) | 0.58229 (12) | 0.09359 (7) | 0.0363 (3) | |
C17 | 0.15563 (19) | 0.64889 (15) | 0.03282 (8) | 0.0524 (4) | |
H17A | 0.0631 | 0.6731 | 0.0439 | 0.079* | |
H17B | 0.1349 | 0.5992 | −0.0076 | 0.079* | |
H17C | 0.2102 | 0.7167 | 0.0235 | 0.079* | |
C18 | 0.16079 (18) | 0.47746 (14) | 0.10892 (8) | 0.0469 (4) | |
H18A | 0.0684 | 0.5030 | 0.1197 | 0.070* | |
H18B | 0.2187 | 0.4355 | 0.1480 | 0.070* | |
H18C | 0.1396 | 0.4270 | 0.0689 | 0.070* | |
C15 | 0.28560 (15) | 0.66223 (11) | 0.15556 (7) | 0.0333 (3) | |
H15A | 0.3177 | 0.7370 | 0.1403 | 0.040* | |
H15B | 0.1952 | 0.6762 | 0.1725 | 0.040* | |
C16 | 0.40305 (13) | 0.61902 (11) | 0.21420 (6) | 0.0268 (3) | |
O16 | 0.41477 (10) | 0.66590 (8) | 0.27109 (4) | 0.0305 (2) | |
C21 | 0.75331 (14) | 0.53822 (11) | 0.28643 (6) | 0.0275 (3) | |
C22 | 0.77700 (14) | 0.63360 (11) | 0.32751 (6) | 0.0272 (3) | |
O22 | 0.67166 (10) | 0.69154 (8) | 0.34823 (5) | 0.0315 (2) | |
H22 | 0.573 (2) | 0.6717 (17) | 0.3213 (10) | 0.064 (6)* | |
C23 | 0.92669 (14) | 0.68318 (11) | 0.35539 (7) | 0.0322 (3) | |
H23A | 0.9311 | 0.7114 | 0.4024 | 0.039* | |
H23B | 0.9414 | 0.7500 | 0.3271 | 0.039* | |
C24 | 1.05194 (14) | 0.59730 (12) | 0.35704 (6) | 0.0310 (3) | |
C27 | 1.19970 (15) | 0.65904 (14) | 0.37372 (7) | 0.0401 (3) | |
H27A | 1.2016 | 0.7186 | 0.3394 | 0.060* | |
H27B | 1.2786 | 0.6036 | 0.3735 | 0.060* | |
H27C | 1.2138 | 0.6946 | 0.4190 | 0.060* | |
C28 | 1.05078 (17) | 0.50375 (14) | 0.41084 (8) | 0.0450 (4) | |
H28A | 1.0664 | 0.5390 | 0.4562 | 0.067* | |
H28B | 1.1294 | 0.4483 | 0.4099 | 0.067* | |
H28C | 0.9559 | 0.4641 | 0.4007 | 0.067* | |
C25 | 1.02709 (15) | 0.54452 (12) | 0.28540 (7) | 0.0350 (3) | |
H25A | 1.0458 | 0.6041 | 0.2531 | 0.042* | |
H25B | 1.0996 | 0.4822 | 0.2860 | 0.042* | |
C26 | 0.87530 (15) | 0.49629 (12) | 0.25914 (7) | 0.0332 (3) | |
O26 | 0.85754 (12) | 0.42344 (10) | 0.21240 (6) | 0.0476 (3) | |
C31 | 0.53302 (14) | 0.43480 (10) | 0.32060 (6) | 0.0276 (3) | |
C32 | 0.40599 (15) | 0.36826 (11) | 0.30212 (7) | 0.0317 (3) | |
H32 | 0.3612 | 0.3590 | 0.2551 | 0.038* | |
C33 | 0.34367 (16) | 0.31524 (12) | 0.35114 (8) | 0.0376 (3) | |
H33 | 0.2579 | 0.2698 | 0.3369 | 0.045* | |
C34 | 0.40495 (17) | 0.32753 (12) | 0.42086 (7) | 0.0399 (3) | |
C341 | 0.3387 (2) | 0.26899 (16) | 0.47453 (9) | 0.0578 (5) | |
H34A | 0.4173 | 0.2436 | 0.5124 | 0.087* | |
H34B | 0.2810 | 0.2024 | 0.4542 | 0.087* | |
H34C | 0.2748 | 0.3232 | 0.4916 | 0.087* | |
C35 | 0.52969 (17) | 0.39499 (12) | 0.43914 (7) | 0.0387 (3) | |
H35 | 0.5728 | 0.4058 | 0.4862 | 0.046* | |
C36 | 0.59364 (16) | 0.44738 (11) | 0.39024 (7) | 0.0333 (3) | |
H36 | 0.6798 | 0.4923 | 0.4046 | 0.040* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0329 (6) | 0.0228 (6) | 0.0250 (6) | 0.0030 (5) | 0.0067 (5) | −0.0026 (5) |
C11 | 0.0307 (6) | 0.0262 (6) | 0.0239 (6) | −0.0040 (5) | 0.0042 (5) | 0.0002 (5) |
C12 | 0.0393 (7) | 0.0339 (7) | 0.0281 (6) | −0.0068 (6) | 0.0073 (5) | −0.0043 (5) |
O12 | 0.0530 (7) | 0.0578 (7) | 0.0316 (5) | 0.0050 (5) | 0.0103 (5) | −0.0147 (5) |
C13 | 0.0509 (9) | 0.0461 (8) | 0.0232 (6) | −0.0116 (7) | 0.0030 (6) | −0.0008 (6) |
C14 | 0.0393 (7) | 0.0354 (7) | 0.0290 (6) | −0.0121 (6) | −0.0035 (5) | 0.0062 (5) |
C17 | 0.0557 (10) | 0.0526 (10) | 0.0383 (8) | −0.0136 (8) | −0.0128 (7) | 0.0122 (7) |
C18 | 0.0482 (9) | 0.0412 (8) | 0.0444 (8) | −0.0207 (7) | −0.0048 (7) | 0.0062 (7) |
C15 | 0.0328 (7) | 0.0294 (6) | 0.0336 (7) | −0.0048 (5) | −0.0013 (5) | 0.0067 (5) |
C16 | 0.0287 (6) | 0.0249 (6) | 0.0267 (6) | −0.0060 (5) | 0.0055 (5) | 0.0038 (5) |
O16 | 0.0311 (5) | 0.0317 (5) | 0.0284 (5) | 0.0040 (4) | 0.0057 (4) | 0.0005 (4) |
C21 | 0.0303 (6) | 0.0262 (6) | 0.0255 (6) | 0.0038 (5) | 0.0049 (5) | −0.0004 (5) |
C22 | 0.0315 (6) | 0.0254 (6) | 0.0241 (6) | 0.0056 (5) | 0.0048 (5) | 0.0005 (5) |
O22 | 0.0301 (5) | 0.0290 (5) | 0.0339 (5) | 0.0071 (4) | 0.0042 (4) | −0.0062 (4) |
C23 | 0.0317 (7) | 0.0303 (7) | 0.0333 (7) | 0.0036 (5) | 0.0044 (5) | −0.0056 (5) |
C24 | 0.0303 (6) | 0.0351 (7) | 0.0280 (6) | 0.0061 (5) | 0.0073 (5) | 0.0004 (5) |
C27 | 0.0324 (7) | 0.0525 (9) | 0.0348 (7) | 0.0017 (6) | 0.0061 (6) | −0.0052 (6) |
C28 | 0.0404 (8) | 0.0543 (9) | 0.0416 (8) | 0.0139 (7) | 0.0118 (6) | 0.0151 (7) |
C25 | 0.0329 (7) | 0.0409 (7) | 0.0332 (7) | 0.0030 (6) | 0.0114 (5) | −0.0050 (6) |
C26 | 0.0382 (7) | 0.0317 (7) | 0.0305 (6) | 0.0036 (6) | 0.0096 (5) | −0.0047 (5) |
O26 | 0.0427 (6) | 0.0516 (7) | 0.0508 (6) | −0.0006 (5) | 0.0157 (5) | −0.0259 (5) |
C31 | 0.0351 (7) | 0.0212 (6) | 0.0270 (6) | 0.0081 (5) | 0.0077 (5) | 0.0020 (5) |
C32 | 0.0371 (7) | 0.0265 (6) | 0.0319 (6) | 0.0056 (5) | 0.0082 (5) | 0.0034 (5) |
C33 | 0.0399 (8) | 0.0303 (7) | 0.0457 (8) | 0.0063 (6) | 0.0161 (6) | 0.0078 (6) |
C34 | 0.0516 (9) | 0.0328 (7) | 0.0408 (8) | 0.0186 (6) | 0.0220 (7) | 0.0131 (6) |
C341 | 0.0710 (12) | 0.0565 (10) | 0.0562 (10) | 0.0224 (9) | 0.0359 (9) | 0.0259 (8) |
C35 | 0.0561 (9) | 0.0336 (7) | 0.0279 (6) | 0.0172 (7) | 0.0123 (6) | 0.0052 (5) |
C36 | 0.0429 (8) | 0.0280 (6) | 0.0283 (6) | 0.0079 (6) | 0.0062 (5) | 0.0012 (5) |
Geometric parameters (Å, º) top
C1—C21 | 1.5234 (18) | C23—C24 | 1.5334 (18) |
C1—C11 | 1.5263 (17) | C23—H23A | 0.9900 |
C1—C31 | 1.5401 (17) | C23—H23B | 0.9900 |
C1—H1 | 1.0000 | C24—C27 | 1.526 (2) |
C11—C12 | 1.3688 (17) | C24—C25 | 1.5326 (18) |
C11—C16 | 1.4460 (18) | C24—C28 | 1.5345 (19) |
C12—O12 | 1.3358 (18) | C27—H27A | 0.9800 |
C12—C13 | 1.500 (2) | C27—H27B | 0.9800 |
O12—H12 | 0.98 (2) | C27—H27C | 0.9800 |
C13—C14 | 1.529 (2) | C28—H28A | 0.9800 |
C13—H13A | 0.9900 | C28—H28B | 0.9800 |
C13—H13B | 0.9900 | C28—H28C | 0.9800 |
C14—C15 | 1.5303 (19) | C25—C26 | 1.5082 (19) |
C14—C18 | 1.5336 (19) | C25—H25A | 0.9900 |
C14—C17 | 1.5385 (19) | C25—H25B | 0.9900 |
C17—H17A | 0.9800 | C26—O26 | 1.2476 (16) |
C17—H17B | 0.9800 | C31—C36 | 1.3948 (18) |
C17—H17C | 0.9800 | C31—C32 | 1.3971 (19) |
C18—H18A | 0.9800 | C32—C33 | 1.3914 (19) |
C18—H18B | 0.9800 | C32—H32 | 0.9500 |
C18—H18C | 0.9800 | C33—C34 | 1.397 (2) |
C15—C16 | 1.5079 (17) | C33—H33 | 0.9500 |
C15—H15A | 0.9900 | C34—C35 | 1.386 (2) |
C15—H15B | 0.9900 | C34—C341 | 1.516 (2) |
C16—O16 | 1.2475 (15) | C341—H34A | 0.9800 |
C21—C22 | 1.3712 (17) | C341—H34B | 0.9800 |
C21—C26 | 1.4520 (18) | C341—H34C | 0.9800 |
C22—O22 | 1.3320 (15) | C35—C36 | 1.395 (2) |
C22—C23 | 1.5025 (18) | C35—H35 | 0.9500 |
O22—H22 | 0.99 (2) | C36—H36 | 0.9500 |
| | | |
C21—C1—C11 | 114.73 (10) | C24—C23—H23A | 108.8 |
C21—C1—C31 | 116.25 (10) | C22—C23—H23B | 108.8 |
C11—C1—C31 | 113.15 (10) | C24—C23—H23B | 108.8 |
C21—C1—H1 | 103.5 | H23A—C23—H23B | 107.7 |
C11—C1—H1 | 103.5 | C27—C24—C25 | 109.76 (11) |
C31—C1—H1 | 103.5 | C27—C24—C23 | 110.28 (11) |
C12—C11—C16 | 117.81 (12) | C25—C24—C23 | 106.43 (11) |
C12—C11—C1 | 121.86 (12) | C27—C24—C28 | 108.97 (12) |
C16—C11—C1 | 120.22 (10) | C25—C24—C28 | 110.58 (12) |
O12—C12—C11 | 124.12 (13) | C23—C24—C28 | 110.78 (11) |
O12—C12—C13 | 112.52 (12) | C24—C27—H27A | 109.5 |
C11—C12—C13 | 123.35 (13) | C24—C27—H27B | 109.5 |
C12—O12—H12 | 112.1 (12) | H27A—C27—H27B | 109.5 |
C12—C13—C14 | 113.65 (11) | C24—C27—H27C | 109.5 |
C12—C13—H13A | 108.8 | H27A—C27—H27C | 109.5 |
C14—C13—H13A | 108.8 | H27B—C27—H27C | 109.5 |
C12—C13—H13B | 108.8 | C24—C28—H28A | 109.5 |
C14—C13—H13B | 108.8 | C24—C28—H28B | 109.5 |
H13A—C13—H13B | 107.7 | H28A—C28—H28B | 109.5 |
C13—C14—C15 | 107.34 (11) | C24—C28—H28C | 109.5 |
C13—C14—C18 | 110.50 (13) | H28A—C28—H28C | 109.5 |
C15—C14—C18 | 111.05 (12) | H28B—C28—H28C | 109.5 |
C13—C14—C17 | 109.56 (13) | C26—C25—C24 | 114.47 (11) |
C15—C14—C17 | 109.06 (12) | C26—C25—H25A | 108.6 |
C18—C14—C17 | 109.30 (12) | C24—C25—H25A | 108.6 |
C14—C17—H17A | 109.5 | C26—C25—H25B | 108.6 |
C14—C17—H17B | 109.5 | C24—C25—H25B | 108.6 |
H17A—C17—H17B | 109.5 | H25A—C25—H25B | 107.6 |
C14—C17—H17C | 109.5 | O26—C26—C21 | 121.68 (13) |
H17A—C17—H17C | 109.5 | O26—C26—C25 | 118.38 (12) |
H17B—C17—H17C | 109.5 | C21—C26—C25 | 119.90 (11) |
C14—C18—H18A | 109.5 | C36—C31—C32 | 117.30 (12) |
C14—C18—H18B | 109.5 | C36—C31—C1 | 124.15 (12) |
H18A—C18—H18B | 109.5 | C32—C31—C1 | 117.96 (11) |
C14—C18—H18C | 109.5 | C33—C32—C31 | 121.38 (13) |
H18A—C18—H18C | 109.5 | C33—C32—H32 | 119.3 |
H18B—C18—H18C | 109.5 | C31—C32—H32 | 119.3 |
C16—C15—C14 | 115.44 (11) | C32—C33—C34 | 121.23 (14) |
C16—C15—H15A | 108.4 | C32—C33—H33 | 119.4 |
C14—C15—H15A | 108.4 | C34—C33—H33 | 119.4 |
C16—C15—H15B | 108.4 | C35—C34—C33 | 117.32 (13) |
C14—C15—H15B | 108.4 | C35—C34—C341 | 121.14 (15) |
H15A—C15—H15B | 107.5 | C33—C34—C341 | 121.53 (16) |
O16—C16—C11 | 121.82 (11) | C34—C341—H34A | 109.5 |
O16—C16—C15 | 118.06 (11) | C34—C341—H34B | 109.5 |
C11—C16—C15 | 120.06 (11) | H34A—C341—H34B | 109.5 |
C22—C21—C26 | 117.50 (12) | C34—C341—H34C | 109.5 |
C22—C21—C1 | 126.16 (11) | H34A—C341—H34C | 109.5 |
C26—C21—C1 | 116.26 (11) | H34B—C341—H34C | 109.5 |
O22—C22—C21 | 124.36 (12) | C34—C35—C36 | 121.74 (13) |
O22—C22—C23 | 112.34 (10) | C34—C35—H35 | 119.1 |
C21—C22—C23 | 123.30 (11) | C36—C35—H35 | 119.1 |
C22—O22—H22 | 111.9 (11) | C31—C36—C35 | 121.02 (14) |
C22—C23—C24 | 113.63 (11) | C31—C36—H36 | 119.5 |
C22—C23—H23A | 108.8 | C35—C36—H36 | 119.5 |
| | | |
C21—C1—C11—C12 | 89.99 (14) | C1—C21—C22—C23 | 171.99 (12) |
C31—C1—C11—C12 | −133.42 (12) | O22—C22—C23—C24 | 157.51 (11) |
C21—C1—C11—C16 | −86.20 (14) | C21—C22—C23—C24 | −21.41 (18) |
C31—C1—C11—C16 | 50.39 (15) | C22—C23—C24—C27 | 169.95 (11) |
C16—C11—C12—O12 | 169.84 (12) | C22—C23—C24—C25 | 50.94 (14) |
C1—C11—C12—O12 | −6.4 (2) | C22—C23—C24—C28 | −69.32 (15) |
C16—C11—C12—C13 | −8.70 (19) | C27—C24—C25—C26 | −171.44 (12) |
C1—C11—C12—C13 | 175.02 (12) | C23—C24—C25—C26 | −52.09 (15) |
O12—C12—C13—C14 | 157.29 (12) | C28—C24—C25—C26 | 68.30 (15) |
C11—C12—C13—C14 | −24.02 (19) | C22—C21—C26—O26 | −167.32 (13) |
C12—C13—C14—C15 | 50.13 (15) | C1—C21—C26—O26 | 9.78 (19) |
C12—C13—C14—C18 | −71.10 (15) | C22—C21—C26—C25 | 10.20 (18) |
C12—C13—C14—C17 | 168.42 (12) | C1—C21—C26—C25 | −172.71 (11) |
C13—C14—C15—C16 | −48.07 (15) | C24—C25—C26—O26 | −158.99 (13) |
C18—C14—C15—C16 | 72.81 (16) | C24—C25—C26—C21 | 23.42 (18) |
C17—C14—C15—C16 | −166.68 (12) | C21—C1—C31—C36 | −3.99 (17) |
C12—C11—C16—O16 | −165.99 (12) | C11—C1—C31—C36 | −139.89 (12) |
C1—C11—C16—O16 | 10.36 (18) | C21—C1—C31—C32 | −174.95 (11) |
C12—C11—C16—C15 | 11.34 (17) | C11—C1—C31—C32 | 49.16 (15) |
C1—C11—C16—C15 | −172.31 (11) | C36—C31—C32—C33 | −0.94 (18) |
C14—C15—C16—O16 | −163.65 (11) | C1—C31—C32—C33 | 170.64 (11) |
C14—C15—C16—C11 | 18.93 (17) | C31—C32—C33—C34 | 0.7 (2) |
C11—C1—C21—C22 | 81.04 (15) | C32—C33—C34—C35 | 0.3 (2) |
C31—C1—C21—C22 | −54.17 (17) | C32—C33—C34—C341 | −179.32 (13) |
C11—C1—C21—C26 | −95.76 (13) | C33—C34—C35—C36 | −1.0 (2) |
C31—C1—C21—C26 | 129.03 (12) | C341—C34—C35—C36 | 178.62 (13) |
C26—C21—C22—O22 | 169.98 (11) | C32—C31—C36—C35 | 0.24 (18) |
C1—C21—C22—O22 | −6.8 (2) | C1—C31—C36—C35 | −170.77 (12) |
C26—C21—C22—C23 | −11.24 (18) | C34—C35—C36—C31 | 0.7 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O12—H12···O26 | 0.98 (2) | 1.73 (2) | 2.6946 (16) | 168 (2) |
O22—H22···O16 | 0.99 (2) | 1.60 (2) | 2.5714 (13) | 168.0 (18) |
Crystal data top
C24H30O5 | F(000) = 856 |
Mr = 398.48 | Dx = 1.228 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.916 (2) Å | Cell parameters from 5837 reflections |
b = 11.573 (2) Å | θ = 0–25° |
c = 21.106 (5) Å | µ = 0.09 mm−1 |
β = 98.15 (1)° | T = 173 K |
V = 2155.8 (8) Å3 | Block, colourless |
Z = 4 | 0.70 × 0.40 × 0.30 mm |
Data collection top
Siemens CCD three-circle diffractometer | 4937 independent reflections |
Radiation source: fine-focus sealed tube | 3429 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
ω scans | θmax = 27.5°, θmin = 2.0° |
Absorption correction: empirical (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.943, Tmax = 0.975 | k = −15→15 |
40510 measured reflections | l = −27→27 |
Refinement top
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)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0411P)2 + 1.1616P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
4937 reflections | Δρmax = 0.28 e Å−3 |
271 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0055 (7) |
Special details top
Experimental. ; |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 >
σ(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.82530 (18) | 0.51194 (14) | 0.73424 (7) | 0.0263 (4) | |
H1 | 0.8770 | 0.5829 | 0.7535 | 0.032* | |
C11 | 0.76832 (19) | 0.45263 (14) | 0.79124 (7) | 0.0274 (4) | |
C12 | 0.8310 (2) | 0.47770 (15) | 0.85297 (8) | 0.0349 (4) | |
O12 | 0.95248 (17) | 0.54521 (12) | 0.86878 (7) | 0.0467 (4) | |
H12 | 1.007 (3) | 0.560 (2) | 0.8347 (13) | 0.087 (9)* | |
C13 | 0.7711 (2) | 0.42951 (17) | 0.91050 (8) | 0.0428 (5) | |
H13A | 0.7797 | 0.4895 | 0.9443 | 0.051* | |
H13B | 0.8354 | 0.3635 | 0.9272 | 0.051* | |
C14 | 0.6058 (2) | 0.38888 (16) | 0.89720 (8) | 0.0391 (5) | |
C17 | 0.5677 (3) | 0.31637 (19) | 0.95391 (9) | 0.0533 (6) | |
H17A | 0.5785 | 0.3642 | 0.9926 | 0.080* | |
H17B | 0.6372 | 0.2505 | 0.9607 | 0.080* | |
H17C | 0.4633 | 0.2882 | 0.9446 | 0.080* | |
C18 | 0.4976 (3) | 0.49287 (19) | 0.88693 (11) | 0.0590 (7) | |
H18A | 0.5097 | 0.5409 | 0.9256 | 0.089* | |
H18B | 0.3928 | 0.4652 | 0.8781 | 0.089* | |
H18C | 0.5214 | 0.5387 | 0.8506 | 0.089* | |
C15 | 0.5886 (2) | 0.31344 (15) | 0.83700 (8) | 0.0334 (4) | |
H15A | 0.6381 | 0.2381 | 0.8481 | 0.040* | |
H15B | 0.4794 | 0.2984 | 0.8236 | 0.040* | |
C16 | 0.65382 (18) | 0.36374 (14) | 0.78094 (8) | 0.0268 (4) | |
O16 | 0.60897 (13) | 0.32244 (10) | 0.72668 (5) | 0.0307 (3) | |
C21 | 0.95100 (18) | 0.44752 (14) | 0.70696 (7) | 0.0260 (3) | |
C22 | 0.93272 (18) | 0.35419 (14) | 0.66663 (7) | 0.0250 (3) | |
O22 | 0.80136 (13) | 0.29910 (10) | 0.64860 (6) | 0.0285 (3) | |
H22 | 0.730 (3) | 0.319 (2) | 0.6760 (12) | 0.071 (8)* | |
C23 | 1.06029 (18) | 0.30249 (14) | 0.63670 (8) | 0.0295 (4) | |
H23A | 1.0204 | 0.2756 | 0.5930 | 0.035* | |
H23B | 1.0996 | 0.2342 | 0.6620 | 0.035* | |
C24 | 1.19148 (19) | 0.38673 (15) | 0.63261 (8) | 0.0303 (4) | |
C27 | 1.3256 (2) | 0.32132 (18) | 0.61188 (9) | 0.0406 (5) | |
H27A | 1.4092 | 0.3752 | 0.6092 | 0.061* | |
H27B | 1.2945 | 0.2859 | 0.5699 | 0.061* | |
H27C | 1.3589 | 0.2609 | 0.6433 | 0.061* | |
C28 | 1.1410 (2) | 0.48334 (17) | 0.58372 (9) | 0.0418 (5) | |
H28A | 1.0549 | 0.5251 | 0.5969 | 0.063* | |
H28B | 1.1109 | 0.4491 | 0.5413 | 0.063* | |
H28C | 1.2252 | 0.5371 | 0.5819 | 0.063* | |
C25 | 1.23590 (19) | 0.43671 (16) | 0.70022 (8) | 0.0337 (4) | |
H25A | 1.2852 | 0.3751 | 0.7283 | 0.040* | |
H25B | 1.3114 | 0.4988 | 0.6982 | 0.040* | |
C26 | 1.1054 (2) | 0.48496 (15) | 0.73009 (8) | 0.0314 (4) | |
O26 | 1.13391 (14) | 0.55430 (12) | 0.77591 (6) | 0.0443 (3) | |
C31 | 0.69506 (18) | 0.56040 (13) | 0.68500 (7) | 0.0251 (3) | |
C32 | 0.58910 (19) | 0.63297 (14) | 0.70822 (8) | 0.0273 (4) | |
H32 | 0.5917 | 0.6411 | 0.7531 | 0.033* | |
C33 | 0.48054 (19) | 0.69318 (14) | 0.66740 (8) | 0.0299 (4) | |
H33 | 0.4109 | 0.7421 | 0.6847 | 0.036* | |
C34 | 0.47303 (19) | 0.68223 (14) | 0.60104 (8) | 0.0282 (4) | |
O341 | 0.36203 (14) | 0.74640 (11) | 0.56478 (6) | 0.0368 (3) | |
C341 | 0.3500 (2) | 0.73812 (19) | 0.49658 (9) | 0.0447 (5) | |
H34A | 0.2672 | 0.7877 | 0.4768 | 0.067* | |
H34B | 0.3291 | 0.6579 | 0.4834 | 0.067* | |
H34C | 0.4453 | 0.7631 | 0.4828 | 0.067* | |
C35 | 0.57546 (19) | 0.61018 (14) | 0.57668 (8) | 0.0286 (4) | |
H35 | 0.5710 | 0.6008 | 0.5317 | 0.034* | |
C36 | 0.68599 (19) | 0.55096 (14) | 0.61880 (8) | 0.0272 (4) | |
H36 | 0.7566 | 0.5030 | 0.6015 | 0.033* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0309 (9) | 0.0224 (8) | 0.0250 (8) | −0.0019 (7) | 0.0024 (7) | −0.0026 (6) |
C11 | 0.0345 (9) | 0.0246 (8) | 0.0231 (8) | 0.0058 (7) | 0.0047 (7) | −0.0004 (6) |
C12 | 0.0471 (11) | 0.0282 (9) | 0.0284 (9) | 0.0067 (8) | 0.0014 (8) | −0.0043 (7) |
O12 | 0.0563 (9) | 0.0486 (8) | 0.0322 (7) | −0.0070 (7) | −0.0037 (7) | −0.0103 (6) |
C13 | 0.0690 (14) | 0.0378 (10) | 0.0216 (9) | 0.0094 (10) | 0.0058 (9) | −0.0019 (8) |
C14 | 0.0597 (13) | 0.0323 (10) | 0.0288 (9) | 0.0165 (9) | 0.0181 (9) | 0.0055 (8) |
C17 | 0.0814 (16) | 0.0501 (12) | 0.0336 (11) | 0.0156 (12) | 0.0259 (11) | 0.0075 (9) |
C18 | 0.0848 (17) | 0.0476 (12) | 0.0513 (13) | 0.0334 (12) | 0.0326 (12) | 0.0076 (10) |
C15 | 0.0418 (10) | 0.0296 (9) | 0.0312 (9) | 0.0076 (8) | 0.0131 (8) | 0.0055 (7) |
C16 | 0.0292 (9) | 0.0263 (8) | 0.0256 (8) | 0.0091 (7) | 0.0061 (7) | 0.0029 (7) |
O16 | 0.0312 (6) | 0.0346 (6) | 0.0268 (6) | −0.0036 (5) | 0.0062 (5) | −0.0001 (5) |
C21 | 0.0281 (8) | 0.0243 (8) | 0.0251 (8) | −0.0014 (7) | 0.0019 (6) | 0.0010 (6) |
C22 | 0.0260 (8) | 0.0247 (8) | 0.0240 (8) | −0.0031 (7) | 0.0025 (6) | 0.0028 (6) |
O22 | 0.0270 (6) | 0.0294 (6) | 0.0298 (6) | −0.0066 (5) | 0.0064 (5) | −0.0035 (5) |
C23 | 0.0297 (9) | 0.0284 (9) | 0.0312 (9) | −0.0015 (7) | 0.0066 (7) | −0.0021 (7) |
C24 | 0.0254 (8) | 0.0346 (9) | 0.0308 (9) | −0.0032 (7) | 0.0034 (7) | 0.0020 (7) |
C27 | 0.0292 (9) | 0.0556 (12) | 0.0377 (10) | −0.0004 (9) | 0.0072 (8) | −0.0022 (9) |
C28 | 0.0384 (11) | 0.0459 (11) | 0.0411 (11) | −0.0062 (9) | 0.0054 (8) | 0.0123 (9) |
C25 | 0.0260 (9) | 0.0370 (10) | 0.0370 (10) | −0.0045 (8) | 0.0005 (7) | −0.0004 (8) |
C26 | 0.0327 (9) | 0.0277 (9) | 0.0320 (9) | −0.0030 (7) | −0.0015 (7) | 0.0001 (7) |
O26 | 0.0375 (7) | 0.0454 (8) | 0.0473 (8) | −0.0051 (6) | −0.0029 (6) | −0.0175 (6) |
C31 | 0.0284 (8) | 0.0200 (8) | 0.0265 (8) | −0.0049 (6) | 0.0029 (6) | 0.0014 (6) |
C32 | 0.0336 (9) | 0.0246 (8) | 0.0238 (8) | −0.0036 (7) | 0.0052 (7) | −0.0012 (6) |
C33 | 0.0328 (9) | 0.0260 (8) | 0.0316 (9) | 0.0001 (7) | 0.0067 (7) | −0.0021 (7) |
C34 | 0.0286 (9) | 0.0244 (8) | 0.0304 (9) | −0.0029 (7) | 0.0002 (7) | 0.0041 (7) |
O341 | 0.0391 (7) | 0.0380 (7) | 0.0320 (7) | 0.0081 (6) | 0.0005 (5) | 0.0040 (5) |
C341 | 0.0501 (12) | 0.0508 (12) | 0.0310 (10) | 0.0101 (10) | −0.0016 (9) | 0.0081 (9) |
C35 | 0.0345 (9) | 0.0275 (8) | 0.0236 (8) | −0.0040 (7) | 0.0035 (7) | −0.0002 (7) |
C36 | 0.0314 (9) | 0.0234 (8) | 0.0272 (8) | −0.0012 (7) | 0.0054 (7) | −0.0010 (7) |
Geometric parameters (Å, º) top
C1—C21 | 1.525 (2) | C23—H23A | 0.9900 |
C1—C11 | 1.533 (2) | C23—H23B | 0.9900 |
C1—C31 | 1.549 (2) | C24—C27 | 1.530 (2) |
C1—H1 | 1.0000 | C24—C25 | 1.539 (2) |
C11—C12 | 1.374 (2) | C24—C28 | 1.545 (2) |
C11—C16 | 1.444 (2) | C27—H27A | 0.9800 |
C12—O12 | 1.339 (2) | C27—H27B | 0.9800 |
C12—C13 | 1.502 (3) | C27—H27C | 0.9800 |
O12—H12 | 0.94 (3) | C28—H28A | 0.9800 |
C13—C14 | 1.535 (3) | C28—H28B | 0.9800 |
C13—H13A | 0.9900 | C28—H28C | 0.9800 |
C13—H13B | 0.9900 | C25—C26 | 1.507 (2) |
C14—C15 | 1.531 (2) | C25—H25A | 0.9900 |
C14—C18 | 1.538 (3) | C25—H25B | 0.9900 |
C14—C17 | 1.539 (3) | C26—O26 | 1.255 (2) |
C17—H17A | 0.9800 | C31—C36 | 1.392 (2) |
C17—H17B | 0.9800 | C31—C32 | 1.403 (2) |
C17—H17C | 0.9800 | C32—C33 | 1.389 (2) |
C18—H18A | 0.9800 | C32—H32 | 0.9500 |
C18—H18B | 0.9800 | C33—C34 | 1.398 (2) |
C18—H18C | 0.9800 | C33—H33 | 0.9500 |
C15—C16 | 1.507 (2) | C34—O341 | 1.379 (2) |
C15—H15A | 0.9900 | C34—C35 | 1.388 (2) |
C15—H15B | 0.9900 | O341—C341 | 1.431 (2) |
C16—O16 | 1.2531 (19) | C341—H34A | 0.9800 |
C21—C22 | 1.371 (2) | C341—H34B | 0.9800 |
C21—C26 | 1.460 (2) | C341—H34C | 0.9800 |
C22—O22 | 1.3404 (19) | C35—C36 | 1.408 (2) |
C22—C23 | 1.501 (2) | C35—H35 | 0.9500 |
O22—H22 | 0.94 (3) | C36—H36 | 0.9500 |
C23—C24 | 1.534 (2) | | |
| | | |
C21—C1—C11 | 114.86 (13) | C22—C23—H23B | 108.9 |
C21—C1—C31 | 116.40 (13) | C24—C23—H23B | 108.9 |
C11—C1—C31 | 112.84 (13) | H23A—C23—H23B | 107.7 |
C21—C1—H1 | 103.5 | C27—C24—C23 | 109.54 (15) |
C11—C1—H1 | 103.5 | C27—C24—C25 | 110.01 (14) |
C31—C1—H1 | 103.5 | C23—C24—C25 | 106.54 (13) |
C12—C11—C16 | 118.50 (15) | C27—C24—C28 | 109.42 (15) |
C12—C11—C1 | 120.93 (16) | C23—C24—C28 | 110.19 (14) |
C16—C11—C1 | 120.46 (14) | C25—C24—C28 | 111.09 (15) |
O12—C12—C11 | 124.45 (17) | C24—C27—H27A | 109.5 |
O12—C12—C13 | 112.54 (16) | C24—C27—H27B | 109.5 |
C11—C12—C13 | 123.00 (17) | H27A—C27—H27B | 109.5 |
C12—O12—H12 | 113.9 (17) | C24—C27—H27C | 109.5 |
C12—C13—C14 | 114.11 (15) | H27A—C27—H27C | 109.5 |
C12—C13—H13A | 108.7 | H27B—C27—H27C | 109.5 |
C14—C13—H13A | 108.7 | C24—C28—H28A | 109.5 |
C12—C13—H13B | 108.7 | C24—C28—H28B | 109.5 |
C14—C13—H13B | 108.7 | H28A—C28—H28B | 109.5 |
H13A—C13—H13B | 107.6 | C24—C28—H28C | 109.5 |
C15—C14—C13 | 107.90 (15) | H28A—C28—H28C | 109.5 |
C15—C14—C18 | 109.99 (16) | H28B—C28—H28C | 109.5 |
C13—C14—C18 | 110.66 (17) | C26—C25—C24 | 114.51 (14) |
C15—C14—C17 | 109.10 (16) | C26—C25—H25A | 108.6 |
C13—C14—C17 | 109.69 (17) | C24—C25—H25A | 108.6 |
C18—C14—C17 | 109.46 (16) | C26—C25—H25B | 108.6 |
C14—C17—H17A | 109.5 | C24—C25—H25B | 108.6 |
C14—C17—H17B | 109.5 | H25A—C25—H25B | 107.6 |
H17A—C17—H17B | 109.5 | O26—C26—C21 | 121.71 (16) |
C14—C17—H17C | 109.5 | O26—C26—C25 | 118.41 (15) |
H17A—C17—H17C | 109.5 | C21—C26—C25 | 119.84 (15) |
H17B—C17—H17C | 109.5 | C36—C31—C32 | 116.82 (15) |
C14—C18—H18A | 109.5 | C36—C31—C1 | 125.18 (15) |
C14—C18—H18B | 109.5 | C32—C31—C1 | 117.39 (14) |
H18A—C18—H18B | 109.5 | C33—C32—C31 | 121.89 (15) |
C14—C18—H18C | 109.5 | C33—C32—H32 | 119.1 |
H18A—C18—H18C | 109.5 | C31—C32—H32 | 119.1 |
H18B—C18—H18C | 109.5 | C32—C33—C34 | 120.41 (15) |
C16—C15—C14 | 115.25 (15) | C32—C33—H33 | 119.8 |
C16—C15—H15A | 108.5 | C34—C33—H33 | 119.8 |
C14—C15—H15A | 108.5 | O341—C34—C35 | 125.17 (15) |
C16—C15—H15B | 108.5 | O341—C34—C33 | 115.84 (15) |
C14—C15—H15B | 108.5 | C35—C34—C33 | 118.99 (15) |
H15A—C15—H15B | 107.5 | C34—O341—C341 | 117.90 (14) |
O16—C16—C11 | 122.44 (15) | O341—C341—H34A | 109.5 |
O16—C16—C15 | 117.48 (15) | O341—C341—H34B | 109.5 |
C11—C16—C15 | 120.03 (15) | H34A—C341—H34B | 109.5 |
C22—C21—C26 | 117.71 (15) | O341—C341—H34C | 109.5 |
C22—C21—C1 | 126.21 (15) | H34A—C341—H34C | 109.5 |
C26—C21—C1 | 115.94 (14) | H34B—C341—H34C | 109.5 |
O22—C22—C21 | 124.98 (15) | C34—C35—C36 | 119.80 (15) |
O22—C22—C23 | 112.00 (14) | C34—C35—H35 | 120.1 |
C21—C22—C23 | 123.02 (15) | C36—C35—H35 | 120.1 |
C22—O22—H22 | 110.2 (15) | C31—C36—C35 | 122.09 (15) |
C22—C23—C24 | 113.54 (14) | C31—C36—H36 | 119.0 |
C22—C23—H23A | 108.9 | C35—C36—H36 | 119.0 |
C24—C23—H23A | 108.9 | | |
| | | |
C21—C1—C11—C12 | 91.70 (19) | O22—C22—C23—C24 | 156.41 (13) |
C31—C1—C11—C12 | −131.68 (16) | C21—C22—C23—C24 | −23.0 (2) |
C21—C1—C11—C16 | −84.39 (19) | C22—C23—C24—C27 | 170.80 (14) |
C31—C1—C11—C16 | 52.24 (19) | C22—C23—C24—C25 | 51.84 (18) |
C16—C11—C12—O12 | 169.76 (16) | C22—C23—C24—C28 | −68.77 (19) |
C1—C11—C12—O12 | −6.4 (3) | C27—C24—C25—C26 | −169.90 (15) |
C16—C11—C12—C13 | −9.0 (3) | C23—C24—C25—C26 | −51.24 (19) |
C1—C11—C12—C13 | 174.83 (15) | C28—C24—C25—C26 | 68.79 (19) |
O12—C12—C13—C14 | 159.54 (15) | C22—C21—C26—O26 | −166.27 (16) |
C11—C12—C13—C14 | −21.6 (2) | C1—C21—C26—O26 | 9.6 (2) |
C12—C13—C14—C15 | 48.2 (2) | C22—C21—C26—C25 | 11.5 (2) |
C12—C13—C14—C18 | −72.2 (2) | C1—C21—C26—C25 | −172.65 (15) |
C12—C13—C14—C17 | 166.90 (15) | C24—C25—C26—O26 | −160.70 (16) |
C13—C14—C15—C16 | −48.22 (19) | C24—C25—C26—C21 | 21.4 (2) |
C18—C14—C15—C16 | 72.6 (2) | C21—C1—C31—C36 | −1.0 (2) |
C17—C14—C15—C16 | −167.34 (16) | C11—C1—C31—C36 | −136.92 (16) |
C12—C11—C16—O16 | −168.02 (15) | C21—C1—C31—C32 | −171.66 (14) |
C1—C11—C16—O16 | 8.2 (2) | C11—C1—C31—C32 | 52.42 (19) |
C12—C11—C16—C15 | 9.3 (2) | C36—C31—C32—C33 | −0.3 (2) |
C1—C11—C16—C15 | −174.56 (14) | C1—C31—C32—C33 | 171.15 (15) |
C14—C15—C16—O16 | −161.40 (15) | C31—C32—C33—C34 | 0.5 (2) |
C14—C15—C16—C11 | 21.2 (2) | C32—C33—C34—O341 | −179.47 (14) |
C11—C1—C21—C22 | 79.2 (2) | C32—C33—C34—C35 | 0.1 (2) |
C31—C1—C21—C22 | −55.8 (2) | C35—C34—O341—C341 | 0.4 (2) |
C11—C1—C21—C26 | −96.23 (17) | C33—C34—O341—C341 | 179.95 (16) |
C31—C1—C21—C26 | 128.73 (15) | O341—C34—C35—C36 | 178.62 (15) |
C26—C21—C22—O22 | 169.95 (15) | C33—C34—C35—C36 | −0.9 (2) |
C1—C21—C22—O22 | −5.4 (3) | C32—C31—C36—C35 | −0.5 (2) |
C26—C21—C22—C23 | −10.8 (2) | C1—C31—C36—C35 | −171.24 (15) |
C1—C21—C22—C23 | 173.87 (15) | C34—C35—C36—C31 | 1.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O12—H12···O26 | 0.94 (3) | 1.79 (3) | 2.714 (2) | 166 (3) |
O22—H22···O16 | 0.94 (3) | 1.63 (3) | 2.5558 (17) | 167 (2) |
Crystal data top
C25H33NO4 | F(000) = 888 |
Mr = 411.52 | Dx = 1.218 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.223 (1) Å | Cell parameters from 8192 reflections |
b = 12.012 (1) Å | θ = 0–25° |
c = 20.661 (1) Å | µ = 0.08 mm−1 |
β = 101.42 (1)° | T = 173 K |
V = 2243.6 (3) Å3 | Block, colourless |
Z = 4 | 0.35 × 0.25 × 0.20 mm |
Data collection top
Siemens CCD three-circle diffractometer | 4957 independent reflections |
Radiation source: fine-focus sealed tube | 3598 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.059 |
ω scans | θmax = 27.1°, θmin = 2.0° |
Absorption correction: empirical (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.972, Tmax = 0.984 | k = −15→15 |
35071 measured reflections | l = −26→26 |
Refinement top
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)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.131 | w = 1/[σ2(Fo2) + (0.045P)2 + 1.8561P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
4957 reflections | Δρmax = 0.35 e Å−3 |
282 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0043 (8) |
Special details top
Experimental. ; |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 >
σ(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.8657 (2) | 0.53018 (17) | 0.74095 (9) | 0.0231 (4) | |
H1 | 0.9160 | 0.6005 | 0.7590 | 0.028* | |
C11 | 0.8191 (2) | 0.47659 (16) | 0.80095 (9) | 0.0231 (4) | |
C12 | 0.8884 (2) | 0.50323 (17) | 0.86411 (10) | 0.0261 (4) | |
O12 | 1.00785 (16) | 0.56829 (13) | 0.87822 (7) | 0.0355 (4) | |
H12 | 1.061 (4) | 0.579 (3) | 0.8393 (17) | 0.099 (12)* | |
C13 | 0.8402 (2) | 0.46069 (19) | 0.92446 (10) | 0.0310 (5) | |
H13A | 0.8560 | 0.5198 | 0.9585 | 0.037* | |
H13B | 0.9033 | 0.3966 | 0.9421 | 0.037* | |
C14 | 0.6771 (2) | 0.42407 (18) | 0.91232 (10) | 0.0284 (5) | |
C17 | 0.5740 (2) | 0.5256 (2) | 0.90163 (11) | 0.0376 (5) | |
H17A | 0.5937 | 0.5729 | 0.9410 | 0.056* | |
H17B | 0.4708 | 0.5005 | 0.8936 | 0.056* | |
H17C | 0.5915 | 0.5681 | 0.8634 | 0.056* | |
C18 | 0.6518 (3) | 0.3580 (2) | 0.97282 (10) | 0.0401 (6) | |
H18A | 0.6696 | 0.4064 | 1.0118 | 0.060* | |
H18B | 0.7200 | 0.2946 | 0.9803 | 0.060* | |
H18C | 0.5496 | 0.3308 | 0.9650 | 0.060* | |
C15 | 0.6493 (2) | 0.34879 (17) | 0.85144 (9) | 0.0267 (4) | |
H15A | 0.6969 | 0.2759 | 0.8638 | 0.032* | |
H15B | 0.5415 | 0.3357 | 0.8383 | 0.032* | |
C16 | 0.7044 (2) | 0.39282 (17) | 0.79255 (9) | 0.0234 (4) | |
O16 | 0.65153 (15) | 0.35120 (12) | 0.73719 (6) | 0.0287 (3) | |
C21 | 0.9861 (2) | 0.46661 (16) | 0.71509 (9) | 0.0240 (4) | |
C22 | 0.9634 (2) | 0.37295 (17) | 0.67564 (9) | 0.0235 (4) | |
O22 | 0.83501 (15) | 0.32114 (12) | 0.65923 (7) | 0.0276 (3) | |
H22 | 0.760 (4) | 0.346 (3) | 0.6886 (16) | 0.083 (10)* | |
C23 | 1.0843 (2) | 0.31913 (17) | 0.64714 (10) | 0.0273 (4) | |
H23A | 1.0415 | 0.2902 | 0.6026 | 0.033* | |
H23B | 1.1243 | 0.2550 | 0.6752 | 0.033* | |
C24 | 1.2118 (2) | 0.39863 (18) | 0.64194 (10) | 0.0284 (5) | |
C27 | 1.3422 (2) | 0.3344 (2) | 0.62404 (11) | 0.0388 (6) | |
H27A | 1.3109 | 0.2993 | 0.5807 | 0.058* | |
H27B | 1.3751 | 0.2769 | 0.6574 | 0.058* | |
H27C | 1.4238 | 0.3859 | 0.6226 | 0.058* | |
C28 | 1.1606 (3) | 0.4871 (2) | 0.58831 (11) | 0.0406 (6) | |
H28A | 1.1298 | 0.4505 | 0.5454 | 0.061* | |
H28B | 1.2423 | 0.5384 | 0.5864 | 0.061* | |
H28C | 1.0771 | 0.5288 | 0.5990 | 0.061* | |
C25 | 1.2610 (2) | 0.45332 (19) | 0.70986 (10) | 0.0328 (5) | |
H25A | 1.3123 | 0.3968 | 0.7411 | 0.039* | |
H25B | 1.3333 | 0.5127 | 0.7062 | 0.039* | |
C26 | 1.1367 (2) | 0.50313 (18) | 0.73830 (10) | 0.0276 (4) | |
O26 | 1.17034 (16) | 0.57352 (14) | 0.78376 (8) | 0.0390 (4) | |
C31 | 0.7331 (2) | 0.57102 (16) | 0.68954 (9) | 0.0235 (4) | |
C32 | 0.6268 (2) | 0.63590 (17) | 0.71198 (10) | 0.0261 (4) | |
H32 | 0.6337 | 0.6440 | 0.7582 | 0.031* | |
C33 | 0.5124 (2) | 0.68855 (17) | 0.66985 (10) | 0.0279 (4) | |
H33 | 0.4435 | 0.7321 | 0.6875 | 0.034* | |
C34 | 0.4967 (2) | 0.67821 (17) | 0.60064 (10) | 0.0275 (4) | |
N34 | 0.3856 (2) | 0.73441 (17) | 0.55816 (9) | 0.0375 (5) | |
C341 | 0.2822 (3) | 0.8036 (2) | 0.58426 (12) | 0.0428 (6) | |
H34D | 0.2188 | 0.8436 | 0.5480 | 0.064* | |
H34E | 0.3369 | 0.8574 | 0.6156 | 0.064* | |
H34F | 0.2208 | 0.7568 | 0.6069 | 0.064* | |
C342 | 0.3579 (3) | 0.7116 (2) | 0.48829 (11) | 0.0468 (6) | |
H34A | 0.2671 | 0.7495 | 0.4667 | 0.070* | |
H34B | 0.3465 | 0.6311 | 0.4810 | 0.070* | |
H34C | 0.4412 | 0.7385 | 0.4697 | 0.070* | |
C35 | 0.6014 (2) | 0.61094 (17) | 0.57772 (10) | 0.0281 (4) | |
H35 | 0.5929 | 0.6002 | 0.5316 | 0.034* | |
C36 | 0.7164 (2) | 0.56017 (17) | 0.62113 (9) | 0.0262 (4) | |
H36 | 0.7858 | 0.5167 | 0.6038 | 0.031* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0225 (9) | 0.0233 (10) | 0.0231 (9) | −0.0021 (8) | 0.0038 (7) | −0.0009 (8) |
C11 | 0.0214 (9) | 0.0245 (10) | 0.0233 (9) | 0.0037 (8) | 0.0041 (7) | 0.0022 (8) |
C12 | 0.0231 (10) | 0.0268 (11) | 0.0274 (10) | 0.0036 (8) | 0.0029 (8) | −0.0025 (8) |
O12 | 0.0309 (8) | 0.0436 (9) | 0.0307 (8) | −0.0093 (7) | 0.0027 (6) | −0.0081 (7) |
C13 | 0.0286 (11) | 0.0396 (12) | 0.0237 (10) | 0.0039 (9) | 0.0024 (8) | −0.0016 (9) |
C14 | 0.0251 (10) | 0.0366 (12) | 0.0242 (10) | 0.0058 (9) | 0.0063 (8) | 0.0008 (9) |
C17 | 0.0335 (12) | 0.0441 (14) | 0.0370 (12) | 0.0099 (10) | 0.0112 (10) | −0.0030 (10) |
C18 | 0.0386 (13) | 0.0571 (16) | 0.0268 (11) | 0.0040 (11) | 0.0119 (9) | 0.0052 (11) |
C15 | 0.0240 (10) | 0.0298 (11) | 0.0271 (10) | 0.0019 (9) | 0.0066 (8) | 0.0027 (8) |
C16 | 0.0198 (9) | 0.0280 (10) | 0.0216 (9) | 0.0054 (8) | 0.0022 (7) | 0.0019 (8) |
O16 | 0.0255 (7) | 0.0354 (8) | 0.0243 (7) | −0.0032 (6) | 0.0025 (6) | −0.0014 (6) |
C21 | 0.0246 (10) | 0.0246 (10) | 0.0225 (9) | −0.0003 (8) | 0.0044 (8) | 0.0009 (8) |
C22 | 0.0238 (10) | 0.0257 (10) | 0.0203 (9) | −0.0008 (8) | 0.0029 (7) | 0.0042 (8) |
O22 | 0.0252 (7) | 0.0315 (8) | 0.0255 (7) | −0.0057 (6) | 0.0037 (6) | −0.0019 (6) |
C23 | 0.0280 (10) | 0.0260 (10) | 0.0275 (10) | −0.0002 (9) | 0.0050 (8) | −0.0031 (8) |
C24 | 0.0234 (10) | 0.0350 (12) | 0.0271 (10) | −0.0004 (9) | 0.0059 (8) | −0.0035 (9) |
C27 | 0.0287 (11) | 0.0516 (15) | 0.0372 (12) | −0.0019 (10) | 0.0093 (9) | −0.0129 (11) |
C28 | 0.0378 (13) | 0.0475 (14) | 0.0378 (12) | −0.0048 (11) | 0.0107 (10) | 0.0071 (11) |
C25 | 0.0246 (10) | 0.0408 (13) | 0.0326 (11) | −0.0034 (9) | 0.0048 (8) | −0.0076 (10) |
C26 | 0.0257 (10) | 0.0302 (11) | 0.0266 (10) | −0.0025 (9) | 0.0044 (8) | −0.0024 (9) |
O26 | 0.0302 (8) | 0.0459 (10) | 0.0409 (9) | −0.0107 (7) | 0.0072 (7) | −0.0194 (8) |
C31 | 0.0250 (10) | 0.0205 (9) | 0.0250 (10) | −0.0020 (8) | 0.0049 (8) | 0.0019 (8) |
C32 | 0.0288 (10) | 0.0252 (10) | 0.0256 (10) | 0.0001 (8) | 0.0083 (8) | −0.0007 (8) |
C33 | 0.0259 (10) | 0.0284 (11) | 0.0308 (11) | 0.0014 (9) | 0.0085 (8) | −0.0005 (9) |
C34 | 0.0245 (10) | 0.0277 (11) | 0.0296 (10) | −0.0021 (8) | 0.0033 (8) | 0.0030 (9) |
N34 | 0.0312 (10) | 0.0479 (12) | 0.0308 (10) | 0.0097 (9) | 0.0000 (8) | 0.0023 (9) |
C341 | 0.0323 (12) | 0.0486 (15) | 0.0446 (14) | 0.0117 (11) | 0.0007 (10) | 0.0053 (11) |
C342 | 0.0538 (15) | 0.0460 (15) | 0.0330 (13) | 0.0093 (12) | −0.0094 (11) | 0.0002 (11) |
C35 | 0.0337 (11) | 0.0287 (11) | 0.0214 (9) | −0.0037 (9) | 0.0044 (8) | −0.0014 (8) |
C36 | 0.0279 (10) | 0.0250 (10) | 0.0264 (10) | 0.0020 (8) | 0.0069 (8) | −0.0019 (8) |
Geometric parameters (Å, º) top
C1—C21 | 1.529 (3) | C24—C27 | 1.534 (3) |
C1—C11 | 1.532 (3) | C24—C25 | 1.534 (3) |
C1—C31 | 1.532 (3) | C24—C28 | 1.541 (3) |
C1—H1 | 1.0000 | C27—H27A | 0.9800 |
C11—C12 | 1.373 (3) | C27—H27B | 0.9800 |
C11—C16 | 1.445 (3) | C27—H27C | 0.9800 |
C12—O12 | 1.335 (2) | C28—H28A | 0.9800 |
C12—C13 | 1.494 (3) | C28—H28B | 0.9800 |
O12—H12 | 1.03 (4) | C28—H28C | 0.9800 |
C13—C14 | 1.540 (3) | C25—C26 | 1.511 (3) |
C13—H13A | 0.9900 | C25—H25A | 0.9900 |
C13—H13B | 0.9900 | C25—H25B | 0.9900 |
C14—C15 | 1.529 (3) | C26—O26 | 1.256 (2) |
C14—C17 | 1.536 (3) | C31—C36 | 1.397 (3) |
C14—C18 | 1.537 (3) | C31—C32 | 1.402 (3) |
C17—H17A | 0.9800 | C32—C33 | 1.381 (3) |
C17—H17B | 0.9800 | C32—H32 | 0.9500 |
C17—H17C | 0.9800 | C33—C34 | 1.414 (3) |
C18—H18A | 0.9800 | C33—H33 | 0.9500 |
C18—H18B | 0.9800 | C34—N34 | 1.386 (3) |
C18—H18C | 0.9800 | C34—C35 | 1.411 (3) |
C15—C16 | 1.505 (3) | N34—C342 | 1.442 (3) |
C15—H15A | 0.9900 | N34—C341 | 1.448 (3) |
C15—H15B | 0.9900 | C341—H34D | 0.9800 |
C16—O16 | 1.255 (2) | C341—H34E | 0.9800 |
C21—C22 | 1.381 (3) | C341—H34F | 0.9800 |
C21—C26 | 1.445 (3) | C342—H34A | 0.9800 |
C22—O22 | 1.321 (2) | C342—H34B | 0.9800 |
C22—C23 | 1.507 (3) | C342—H34C | 0.9800 |
O22—H22 | 1.05 (3) | C35—C36 | 1.387 (3) |
C23—C24 | 1.535 (3) | C35—H35 | 0.9500 |
C23—H23A | 0.9900 | C36—H36 | 0.9500 |
C23—H23B | 0.9900 | | |
| | | |
C21—C1—C11 | 114.36 (16) | C27—C24—C23 | 110.59 (18) |
C21—C1—C31 | 116.91 (16) | C25—C24—C23 | 107.11 (16) |
C11—C1—C31 | 112.49 (15) | C27—C24—C28 | 108.48 (18) |
C21—C1—H1 | 103.7 | C25—C24—C28 | 110.81 (19) |
C11—C1—H1 | 103.7 | C23—C24—C28 | 110.46 (17) |
C31—C1—H1 | 103.7 | C24—C27—H27A | 109.5 |
C12—C11—C16 | 117.96 (17) | C24—C27—H27B | 109.5 |
C12—C11—C1 | 121.25 (18) | H27A—C27—H27B | 109.5 |
C16—C11—C1 | 120.74 (16) | C24—C27—H27C | 109.5 |
O12—C12—C11 | 123.59 (19) | H27A—C27—H27C | 109.5 |
O12—C12—C13 | 112.76 (17) | H27B—C27—H27C | 109.5 |
C11—C12—C13 | 123.63 (19) | C24—C28—H28A | 109.5 |
C12—O12—H12 | 114 (2) | C24—C28—H28B | 109.5 |
C12—C13—C14 | 113.85 (16) | H28A—C28—H28B | 109.5 |
C12—C13—H13A | 108.8 | C24—C28—H28C | 109.5 |
C14—C13—H13A | 108.8 | H28A—C28—H28C | 109.5 |
C12—C13—H13B | 108.8 | H28B—C28—H28C | 109.5 |
C14—C13—H13B | 108.8 | C26—C25—C24 | 114.56 (17) |
H13A—C13—H13B | 107.7 | C26—C25—H25A | 108.6 |
C15—C14—C17 | 110.66 (17) | C24—C25—H25A | 108.6 |
C15—C14—C18 | 109.60 (18) | C26—C25—H25B | 108.6 |
C17—C14—C18 | 109.74 (18) | C24—C25—H25B | 108.6 |
C15—C14—C13 | 107.62 (16) | H25A—C25—H25B | 107.6 |
C17—C14—C13 | 110.75 (19) | O26—C26—C21 | 122.08 (18) |
C18—C14—C13 | 108.42 (17) | O26—C26—C25 | 117.62 (18) |
C14—C17—H17A | 109.5 | C21—C26—C25 | 120.26 (18) |
C14—C17—H17B | 109.5 | C36—C31—C32 | 116.22 (18) |
H17A—C17—H17B | 109.5 | C36—C31—C1 | 125.78 (17) |
C14—C17—H17C | 109.5 | C32—C31—C1 | 117.58 (17) |
H17A—C17—H17C | 109.5 | C33—C32—C31 | 122.93 (18) |
H17B—C17—H17C | 109.5 | C33—C32—H32 | 118.5 |
C14—C18—H18A | 109.5 | C31—C32—H32 | 118.5 |
C14—C18—H18B | 109.5 | C32—C33—C34 | 120.64 (19) |
H18A—C18—H18B | 109.5 | C32—C33—H33 | 119.7 |
C14—C18—H18C | 109.5 | C34—C33—H33 | 119.7 |
H18A—C18—H18C | 109.5 | N34—C34—C35 | 122.40 (18) |
H18B—C18—H18C | 109.5 | N34—C34—C33 | 120.83 (19) |
C16—C15—C14 | 115.38 (17) | C35—C34—C33 | 116.75 (18) |
C16—C15—H15A | 108.4 | C34—N34—C342 | 120.25 (19) |
C14—C15—H15A | 108.4 | C34—N34—C341 | 120.20 (18) |
C16—C15—H15B | 108.4 | C342—N34—C341 | 118.89 (19) |
C14—C15—H15B | 108.4 | N34—C341—H34D | 109.5 |
H15A—C15—H15B | 107.5 | N34—C341—H34E | 109.5 |
O16—C16—C11 | 122.01 (17) | H34D—C341—H34E | 109.5 |
O16—C16—C15 | 117.66 (18) | N34—C341—H34F | 109.5 |
C11—C16—C15 | 120.28 (17) | H34D—C341—H34F | 109.5 |
C22—C21—C26 | 117.84 (18) | H34E—C341—H34F | 109.5 |
C22—C21—C1 | 125.25 (17) | N34—C342—H34A | 109.5 |
C26—C21—C1 | 116.72 (17) | N34—C342—H34B | 109.5 |
O22—C22—C21 | 124.01 (18) | H34A—C342—H34B | 109.5 |
O22—C22—C23 | 113.13 (17) | N34—C342—H34C | 109.5 |
C21—C22—C23 | 122.86 (17) | H34A—C342—H34C | 109.5 |
C22—O22—H22 | 112.2 (18) | H34B—C342—H34C | 109.5 |
C22—C23—C24 | 113.40 (17) | C36—C35—C34 | 121.41 (18) |
C22—C23—H23A | 108.9 | C36—C35—H35 | 119.3 |
C24—C23—H23A | 108.9 | C34—C35—H35 | 119.3 |
C22—C23—H23B | 108.9 | C35—C36—C31 | 122.03 (19) |
C24—C23—H23B | 108.9 | C35—C36—H36 | 119.0 |
H23A—C23—H23B | 107.7 | C31—C36—H36 | 119.0 |
C27—C24—C25 | 109.39 (17) | | |
| | | |
C21—C1—C11—C12 | 90.0 (2) | C21—C22—C23—C24 | −22.9 (3) |
C31—C1—C11—C12 | −133.48 (19) | C22—C23—C24—C27 | 170.25 (17) |
C21—C1—C11—C16 | −87.4 (2) | C22—C23—C24—C25 | 51.1 (2) |
C31—C1—C11—C16 | 49.1 (2) | C22—C23—C24—C28 | −69.6 (2) |
C16—C11—C12—O12 | 171.19 (18) | C27—C24—C25—C26 | −170.35 (19) |
C1—C11—C12—O12 | −6.3 (3) | C23—C24—C25—C26 | −50.5 (2) |
C16—C11—C12—C13 | −7.5 (3) | C28—C24—C25—C26 | 70.1 (2) |
C1—C11—C12—C13 | 174.96 (18) | C22—C21—C26—O26 | −166.32 (19) |
O12—C12—C13—C14 | 158.35 (18) | C1—C21—C26—O26 | 9.0 (3) |
C11—C12—C13—C14 | −22.8 (3) | C22—C21—C26—C25 | 11.2 (3) |
C12—C13—C14—C15 | 48.5 (2) | C1—C21—C26—C25 | −173.50 (18) |
C12—C13—C14—C17 | −72.5 (2) | C24—C25—C26—O26 | −161.41 (19) |
C12—C13—C14—C18 | 167.00 (18) | C24—C25—C26—C21 | 21.0 (3) |
C17—C14—C15—C16 | 73.0 (2) | C21—C1—C31—C36 | −3.4 (3) |
C18—C14—C15—C16 | −165.87 (17) | C11—C1—C31—C36 | −138.7 (2) |
C13—C14—C15—C16 | −48.2 (2) | C21—C1—C31—C32 | −175.76 (17) |
C12—C11—C16—O16 | −168.79 (18) | C11—C1—C31—C32 | 48.9 (2) |
C1—C11—C16—O16 | 8.7 (3) | C36—C31—C32—C33 | −1.1 (3) |
C12—C11—C16—C15 | 8.4 (3) | C1—C31—C32—C33 | 171.98 (19) |
C1—C11—C16—C15 | −174.05 (17) | C31—C32—C33—C34 | 0.5 (3) |
C14—C15—C16—O16 | −161.30 (17) | C32—C33—C34—N34 | −177.4 (2) |
C14—C15—C16—C11 | 21.4 (3) | C32—C33—C34—C35 | 0.9 (3) |
C11—C1—C21—C22 | 79.4 (2) | C35—C34—N34—C342 | 10.3 (3) |
C31—C1—C21—C22 | −55.1 (3) | C33—C34—N34—C342 | −171.5 (2) |
C11—C1—C21—C26 | −95.5 (2) | C35—C34—N34—C341 | −179.1 (2) |
C31—C1—C21—C26 | 129.97 (19) | C33—C34—N34—C341 | −0.9 (3) |
C26—C21—C22—O22 | 169.51 (18) | N34—C34—C35—C36 | 176.5 (2) |
C1—C21—C22—O22 | −5.4 (3) | C33—C34—C35—C36 | −1.8 (3) |
C26—C21—C22—C23 | −10.2 (3) | C34—C35—C36—C31 | 1.3 (3) |
C1—C21—C22—C23 | 174.94 (18) | C32—C31—C36—C35 | 0.2 (3) |
O22—C22—C23—C24 | 157.40 (16) | C1—C31—C36—C35 | −172.23 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O12—H12···O26 | 1.03 (4) | 1.67 (4) | 2.686 (2) | 168 (3) |
O22—H22···O16 | 1.05 (3) | 1.55 (3) | 2.5821 (19) | 166 (3) |