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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101001792/sk1446sup1.cif
Contains datablocks I, II, III, IV, V, VI, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101001792/sk1446Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101001792/sk1446IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101001792/sk1446IIIsup4.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101001792/sk1446IVsup5.hkl
Contains datablock IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101001792/sk1446Vsup6.hkl
Contains datablock V

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101001792/sk1446VIsup7.hkl
Contains datablock VI

CCDC references: 163921; 163922; 163923; 163924; 163925; 163926

Computing details top

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).

(I) ; top
Crystal data top
C23H27FO4Dx = 1.249 Mg m3
Mr = 386.45Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41cdCell parameters from 8192 reflections
Hall symbol: I 41b -2cθ = 0–25°
a = 21.186 (4) ŵ = 0.09 mm1
c = 36.633 (1) ÅT = 173 K
V = 16443 (4) Å3Block, colourless
Z = 320.55 × 0.40 × 0.25 mm
F(000) = 6592
Data collection top
Siemens CCD three-circle
diffractometer
4615 independent reflections
Radiation source: fine-focus sealed tube3818 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.080
ω scansθmax = 27.1°, θmin = 1.8°
Absorption correction: empirical
SADABS (Sheldrick, 1996)
h = 2727
Tmin = 0.952, Tmax = 0.978k = 2727
97175 measured reflectionsl = 4646
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H 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 reflectionsΔρmax = 0.15 e Å3
521 parametersΔρmin = 0.18 e Å3
1 restraintAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute 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
xyzUiso*/Ueq
C10.64131 (12)0.07353 (12)0.03253 (7)0.0264 (6)
H10.67560.05740.04880.032*
C110.62550 (12)0.01750 (11)0.00758 (7)0.0251 (6)
C120.59432 (12)0.02247 (12)0.02539 (7)0.0261 (6)
O120.57074 (9)0.07608 (9)0.03784 (6)0.0317 (4)
H120.565 (2)0.103 (2)0.0173 (12)0.082 (14)*
C130.58287 (13)0.03217 (13)0.05028 (8)0.0299 (6)
H13A0.53890.04680.04690.036*
H13B0.58710.01750.07580.036*
C140.62741 (13)0.08851 (12)0.04445 (7)0.0288 (6)
C170.69266 (13)0.07345 (14)0.06026 (8)0.0369 (7)
H17A0.68870.06420.08640.055*
H17B0.71040.03670.04770.055*
H17C0.72060.10980.05680.055*
C180.60012 (15)0.14703 (13)0.06350 (9)0.0381 (7)
H18A0.59660.13890.08980.057*
H18B0.62810.18320.05940.057*
H18C0.55820.15630.05350.057*
C150.63152 (14)0.10161 (12)0.00348 (8)0.0317 (6)
H15A0.66650.13170.00080.038*
H15B0.59200.12260.00430.038*
C160.64185 (13)0.04440 (12)0.02046 (8)0.0286 (6)
O160.66217 (10)0.05419 (9)0.05248 (6)0.0364 (5)
C210.58762 (12)0.09124 (12)0.05861 (7)0.0256 (6)
C220.58420 (14)0.06575 (12)0.09319 (8)0.0314 (6)
O220.62224 (11)0.02072 (10)0.10510 (6)0.0422 (6)
H220.6409 (19)0.001 (2)0.0880 (11)0.075 (13)*
C230.53579 (15)0.08581 (13)0.12089 (8)0.0352 (7)
H23B0.50090.05470.12090.042*
H23A0.55540.08520.14540.042*
C240.50823 (14)0.15159 (12)0.11402 (8)0.0297 (6)
C270.55671 (16)0.20317 (14)0.12266 (8)0.0396 (7)
H27A0.59400.19760.10710.059*
H27B0.53800.24470.11800.059*
H27C0.56920.20020.14840.059*
C280.45018 (16)0.16086 (15)0.13847 (8)0.0410 (8)
H28A0.41870.12840.13290.061*
H28B0.46270.15740.16410.061*
H28C0.43200.20270.13400.061*
C250.48821 (13)0.15400 (13)0.07381 (7)0.0300 (6)
H25A0.47680.19810.06770.036*
H25B0.44980.12790.07080.036*
C260.53725 (13)0.13156 (12)0.04702 (7)0.0262 (6)
O260.53063 (9)0.14874 (8)0.01408 (5)0.0288 (4)
C310.67098 (12)0.13052 (12)0.01288 (7)0.0272 (6)
C320.70302 (13)0.12332 (14)0.02013 (8)0.0357 (7)
H320.70430.08300.03150.043*
C330.73317 (14)0.17419 (15)0.03677 (9)0.0422 (7)
H330.75450.16920.05940.051*
C340.73119 (15)0.23164 (15)0.01957 (9)0.0427 (8)
F340.76126 (10)0.28159 (9)0.03575 (6)0.0654 (6)
C350.70154 (15)0.24074 (14)0.01287 (10)0.0422 (8)
H350.70130.28110.02410.051*
C360.67152 (13)0.18984 (13)0.02927 (9)0.0345 (7)
H360.65100.19560.05210.041*
C1A0.87922 (13)0.35785 (13)0.21317 (7)0.0302 (6)
H1A0.88310.32250.23110.036*
C11A0.85848 (13)0.41431 (13)0.23621 (7)0.0297 (6)
C12A0.83356 (12)0.46925 (13)0.22292 (7)0.0280 (6)
O12A0.82506 (9)0.48122 (9)0.18756 (6)0.0323 (5)
H12A0.8454 (17)0.4565 (17)0.1735 (10)0.051 (11)*
C13A0.81175 (13)0.52337 (14)0.24653 (8)0.0345 (7)
H13C0.76530.52130.24900.041*
H13D0.82230.56360.23420.041*
C14A0.84128 (14)0.52348 (14)0.28484 (8)0.0372 (7)
C17A0.91120 (15)0.54312 (16)0.28327 (9)0.0467 (8)
H17D0.91450.58620.27370.070*
H17E0.93430.51420.26720.070*
H17F0.92930.54150.30790.070*
C18A0.80577 (18)0.5708 (2)0.30899 (10)0.0603 (11)
H18D0.80950.61320.29850.090*
H18E0.82400.57060.33360.090*
H18F0.76110.55890.31030.090*
C15A0.83603 (16)0.45670 (16)0.29977 (8)0.0439 (8)
H15C0.85550.45510.32430.053*
H15D0.79090.44540.30230.053*
C16A0.86795 (14)0.40922 (15)0.27534 (8)0.0366 (7)
O16A0.90154 (11)0.36665 (10)0.28884 (6)0.0483 (6)
C21A0.94568 (13)0.36506 (13)0.19757 (8)0.0307 (6)
C22A0.99697 (15)0.34079 (14)0.21527 (9)0.0411 (7)
O22A0.99432 (13)0.31441 (12)0.24828 (7)0.0547 (6)
H22A0.964 (2)0.328 (2)0.2615 (13)0.096 (18)*
C23A1.06241 (15)0.34035 (17)0.19979 (11)0.0534 (9)
H23C1.08190.29880.20490.064*
H23D1.08770.37280.21260.064*
C24A1.06608 (14)0.35268 (15)0.15876 (11)0.0456 (8)
C27A1.13439 (16)0.36939 (19)0.14788 (13)0.0674 (12)
H27D1.16210.33360.15330.101*
H27E1.14840.40640.16180.101*
H27F1.13600.37890.12170.101*
C28A1.04535 (16)0.29405 (16)0.13723 (11)0.0530 (9)
H28D1.07320.25860.14320.080*
H28E1.04780.30290.11100.080*
H28F1.00180.28320.14380.080*
C25A1.02240 (14)0.40821 (15)0.14980 (10)0.0467 (8)
H25C1.04150.44740.15960.056*
H25D1.01980.41270.12290.056*
C26A0.95641 (13)0.40199 (13)0.16481 (8)0.0316 (6)
O26A0.91290 (10)0.43100 (9)0.14915 (5)0.0353 (5)
C31A0.82969 (13)0.33444 (12)0.18568 (7)0.0302 (6)
C32A0.76537 (14)0.34507 (13)0.19107 (9)0.0356 (7)
H32A0.75220.36990.21130.043*
C33A0.72015 (15)0.32037 (15)0.16772 (9)0.0405 (7)
H33A0.67650.32800.17180.049*
C34A0.73982 (15)0.28479 (15)0.13874 (9)0.0443 (8)
F34A0.69632 (10)0.26203 (11)0.11451 (5)0.0621 (6)
C35A0.80269 (16)0.27066 (16)0.13273 (9)0.0449 (8)
H35A0.81510.24460.11290.054*
C36A0.84720 (15)0.29583 (14)0.15658 (8)0.0384 (7)
H36A0.89060.28650.15290.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0276 (14)0.0241 (13)0.0274 (14)0.0036 (11)0.0063 (12)0.0013 (11)
C110.0227 (13)0.0236 (13)0.0292 (14)0.0010 (10)0.0044 (11)0.0004 (11)
C120.0222 (13)0.0280 (14)0.0282 (14)0.0006 (11)0.0030 (11)0.0030 (11)
O120.0332 (11)0.0281 (10)0.0337 (11)0.0070 (8)0.0062 (9)0.0001 (9)
C130.0251 (14)0.0342 (15)0.0303 (14)0.0037 (12)0.0004 (12)0.0060 (12)
C140.0283 (14)0.0271 (14)0.0309 (15)0.0024 (11)0.0059 (12)0.0015 (12)
C170.0333 (16)0.0367 (17)0.0407 (18)0.0053 (13)0.0102 (13)0.0051 (13)
C180.0439 (18)0.0305 (15)0.0400 (17)0.0026 (13)0.0053 (14)0.0079 (13)
C150.0354 (15)0.0224 (13)0.0375 (16)0.0045 (11)0.0065 (13)0.0014 (12)
C160.0265 (14)0.0277 (14)0.0315 (16)0.0032 (11)0.0048 (12)0.0002 (12)
O160.0497 (12)0.0286 (10)0.0309 (11)0.0076 (9)0.0024 (10)0.0022 (9)
C210.0283 (14)0.0203 (12)0.0281 (14)0.0001 (11)0.0046 (11)0.0007 (11)
C220.0429 (17)0.0222 (13)0.0290 (15)0.0030 (12)0.0052 (13)0.0014 (12)
O220.0626 (15)0.0366 (12)0.0273 (11)0.0215 (11)0.0028 (10)0.0032 (9)
C230.0530 (19)0.0256 (14)0.0269 (16)0.0046 (13)0.0016 (13)0.0027 (12)
C240.0402 (16)0.0225 (13)0.0263 (13)0.0017 (12)0.0008 (12)0.0002 (11)
C270.0525 (19)0.0317 (16)0.0348 (17)0.0036 (14)0.0057 (14)0.0035 (14)
C280.0507 (19)0.0368 (17)0.0355 (17)0.0045 (14)0.0050 (15)0.0044 (14)
C250.0287 (15)0.0257 (14)0.0357 (16)0.0031 (11)0.0012 (12)0.0017 (12)
C260.0307 (14)0.0175 (12)0.0303 (15)0.0045 (11)0.0039 (12)0.0014 (11)
O260.0321 (10)0.0275 (10)0.0268 (10)0.0024 (8)0.0043 (8)0.0024 (8)
C310.0227 (13)0.0266 (13)0.0325 (15)0.0006 (11)0.0064 (12)0.0052 (12)
C320.0319 (15)0.0306 (15)0.0446 (18)0.0012 (12)0.0040 (13)0.0005 (13)
C330.0347 (16)0.0440 (18)0.0479 (19)0.0073 (14)0.0058 (14)0.0058 (15)
C340.0348 (17)0.0357 (18)0.057 (2)0.0120 (13)0.0047 (15)0.0129 (16)
F340.0691 (14)0.0468 (11)0.0804 (16)0.0305 (10)0.0066 (12)0.0146 (11)
C350.0381 (17)0.0274 (15)0.061 (2)0.0079 (13)0.0104 (16)0.0002 (15)
C360.0316 (15)0.0328 (15)0.0391 (16)0.0040 (12)0.0056 (13)0.0011 (13)
C1A0.0353 (15)0.0300 (15)0.0254 (15)0.0002 (12)0.0058 (12)0.0075 (12)
C11A0.0295 (14)0.0344 (15)0.0252 (14)0.0043 (12)0.0010 (11)0.0004 (12)
C12A0.0210 (13)0.0361 (15)0.0268 (15)0.0056 (11)0.0017 (11)0.0001 (12)
O12A0.0340 (11)0.0346 (11)0.0283 (11)0.0052 (9)0.0019 (9)0.0005 (9)
C13A0.0274 (14)0.0398 (16)0.0364 (16)0.0018 (12)0.0019 (12)0.0037 (13)
C14A0.0353 (16)0.0466 (18)0.0297 (16)0.0018 (13)0.0022 (13)0.0079 (14)
C17A0.0403 (18)0.053 (2)0.047 (2)0.0081 (15)0.0032 (15)0.0128 (17)
C18A0.059 (2)0.076 (3)0.046 (2)0.014 (2)0.0055 (18)0.0233 (19)
C15A0.0432 (18)0.063 (2)0.0252 (16)0.0056 (16)0.0017 (13)0.0004 (15)
C16A0.0367 (16)0.0422 (17)0.0309 (16)0.0092 (14)0.0036 (13)0.0056 (14)
O16A0.0660 (15)0.0463 (13)0.0325 (12)0.0012 (11)0.0135 (11)0.0075 (10)
C21A0.0313 (15)0.0263 (14)0.0344 (16)0.0018 (11)0.0039 (12)0.0049 (12)
C22A0.0393 (17)0.0351 (17)0.049 (2)0.0006 (14)0.0087 (15)0.0070 (15)
O22A0.0513 (15)0.0623 (16)0.0506 (16)0.0099 (13)0.0169 (13)0.0067 (13)
C23A0.0340 (17)0.053 (2)0.073 (3)0.0028 (16)0.0101 (17)0.0198 (19)
C24A0.0304 (16)0.0376 (17)0.069 (2)0.0006 (13)0.0038 (16)0.0187 (16)
C27A0.0375 (19)0.056 (2)0.108 (3)0.0072 (17)0.018 (2)0.030 (2)
C28A0.0462 (19)0.0402 (18)0.073 (2)0.0021 (15)0.0014 (18)0.0227 (18)
C25A0.0384 (17)0.0349 (17)0.067 (2)0.0060 (14)0.0149 (16)0.0079 (16)
C26A0.0353 (16)0.0227 (13)0.0368 (17)0.0040 (12)0.0032 (13)0.0080 (12)
O26A0.0404 (12)0.0319 (11)0.0336 (11)0.0009 (9)0.0031 (9)0.0034 (9)
C31A0.0352 (15)0.0270 (14)0.0283 (14)0.0086 (12)0.0044 (12)0.0066 (12)
C32A0.0375 (17)0.0306 (15)0.0387 (17)0.0057 (12)0.0020 (13)0.0037 (13)
C33A0.0344 (16)0.0385 (17)0.048 (2)0.0100 (13)0.0061 (14)0.0088 (15)
C34A0.0436 (19)0.0478 (19)0.0414 (18)0.0250 (15)0.0112 (15)0.0102 (16)
F34A0.0572 (13)0.0775 (15)0.0517 (12)0.0368 (11)0.0160 (10)0.0004 (11)
C35A0.054 (2)0.0487 (19)0.0315 (17)0.0237 (16)0.0051 (15)0.0050 (15)
C36A0.0383 (16)0.0408 (17)0.0362 (16)0.0146 (13)0.0025 (14)0.0009 (14)
Geometric parameters (Å, º) top
C1—C211.532 (4)C1A—C21A1.527 (4)
C1—C111.535 (4)C1A—C11A1.529 (4)
C1—C311.540 (4)C1A—C31A1.537 (4)
C1—H11.0000C1A—H1A1.0000
C11—C121.381 (4)C11A—C12A1.368 (4)
C11—C161.436 (4)C11A—C16A1.452 (4)
C12—O121.322 (3)C12A—O12A1.332 (3)
C12—C131.494 (4)C12A—C13A1.509 (4)
O12—H120.95 (4)O12A—H12A0.85 (4)
C13—C141.536 (4)C13A—C14A1.536 (4)
C13—H13A0.9900C13A—H13C0.9900
C13—H13B0.9900C13A—H13D0.9900
C14—C151.529 (4)C14A—C15A1.521 (5)
C14—C171.532 (4)C14A—C18A1.534 (4)
C14—C181.536 (4)C14A—C17A1.540 (4)
C17—H17A0.9800C17A—H17D0.9800
C17—H17B0.9800C17A—H17E0.9800
C17—H17C0.9800C17A—H17F0.9800
C18—H18A0.9800C18A—H18D0.9800
C18—H18B0.9800C18A—H18E0.9800
C18—H18C0.9800C18A—H18F0.9800
C15—C161.512 (4)C15A—C16A1.507 (5)
C15—H15A0.9900C15A—H15C0.9900
C15—H15B0.9900C15A—H15D0.9900
C16—O161.267 (3)C16A—O16A1.251 (4)
C21—C221.379 (4)C21A—C22A1.366 (4)
C21—C261.431 (4)C21A—C26A1.451 (4)
C22—O221.323 (3)C22A—O22A1.333 (4)
C22—C231.504 (4)C22A—C23A1.498 (5)
O22—H220.85 (4)O22A—H22A0.86 (5)
C23—C241.532 (4)C23A—C24A1.528 (5)
C23—H23B0.9900C23A—H23C0.9900
C23—H23A0.9900C23A—H23D0.9900
C24—C271.533 (4)C24A—C25A1.532 (5)
C24—C251.534 (4)C24A—C28A1.535 (4)
C24—C281.534 (4)C24A—C27A1.542 (4)
C27—H27A0.9800C27A—H27D0.9800
C27—H27B0.9800C27A—H27E0.9800
C27—H27C0.9800C27A—H27F0.9800
C28—H28A0.9800C28A—H28D0.9800
C28—H28B0.9800C28A—H28E0.9800
C28—H28C0.9800C28A—H28F0.9800
C25—C261.506 (4)C25A—C26A1.508 (4)
C25—H25A0.9900C25A—H25C0.9900
C25—H25B0.9900C25A—H25D0.9900
C26—O261.268 (3)C26A—O26A1.248 (3)
C31—C361.393 (4)C31A—C32A1.395 (4)
C31—C321.395 (4)C31A—C36A1.394 (4)
C32—C331.393 (4)C32A—C33A1.387 (4)
C32—H320.9500C32A—H32A0.9500
C33—C341.371 (5)C33A—C34A1.367 (5)
C33—H330.9500C33A—H33A0.9500
C34—C351.358 (5)C34A—F34A1.367 (3)
C34—F341.370 (3)C34A—C35A1.383 (5)
C35—C361.389 (4)C35A—C36A1.392 (4)
C35—H350.9500C35A—H35A0.9500
C36—H360.9500C36A—H36A0.9500
C21—C1—C11113.5 (2)C21A—C1A—C11A113.2 (2)
C21—C1—C31113.7 (2)C21A—C1A—C31A114.6 (2)
C11—C1—C31114.7 (2)C11A—C1A—C31A114.7 (2)
C21—C1—H1104.5C21A—C1A—H1A104.2
C11—C1—H1104.5C11A—C1A—H1A104.2
C31—C1—H1104.5C31A—C1A—H1A104.2
C12—C11—C16118.2 (2)C12A—C11A—C16A117.9 (3)
C12—C11—C1124.5 (2)C12A—C11A—C1A125.5 (2)
C16—C11—C1117.3 (2)C16A—C11A—C1A116.6 (2)
O12—C12—C11123.2 (2)O12A—C12A—C11A124.1 (3)
O12—C12—C13113.2 (2)O12A—C12A—C13A111.8 (2)
C11—C12—C13123.6 (2)C11A—C12A—C13A124.1 (3)
C12—O12—H12107 (3)C12A—O12A—H12A114 (2)
C12—C13—C14114.7 (2)C12A—C13A—C14A113.6 (2)
C12—C13—H13A108.6C12A—C13A—H13C108.8
C14—C13—H13A108.6C14A—C13A—H13C108.8
C12—C13—H13B108.6C12A—C13A—H13D108.8
C14—C13—H13B108.6C14A—C13A—H13D108.8
H13A—C13—H13B107.6H13C—C13A—H13D107.7
C15—C14—C17110.9 (2)C15A—C14A—C18A111.4 (3)
C15—C14—C13108.2 (2)C15A—C14A—C13A107.3 (2)
C17—C14—C13109.9 (2)C18A—C14A—C13A109.2 (3)
C15—C14—C18108.7 (2)C15A—C14A—C17A109.6 (3)
C17—C14—C18109.6 (2)C18A—C14A—C17A108.5 (3)
C13—C14—C18109.4 (2)C13A—C14A—C17A111.0 (3)
C14—C17—H17A109.5C14A—C17A—H17D109.5
C14—C17—H17B109.5C14A—C17A—H17E109.5
H17A—C17—H17B109.5H17D—C17A—H17E109.5
C14—C17—H17C109.5C14A—C17A—H17F109.5
H17A—C17—H17C109.5H17D—C17A—H17F109.5
H17B—C17—H17C109.5H17E—C17A—H17F109.5
C14—C18—H18A109.5C14A—C18A—H18D109.5
C14—C18—H18B109.5C14A—C18A—H18E109.5
H18A—C18—H18B109.5H18D—C18A—H18E109.5
C14—C18—H18C109.5C14A—C18A—H18F109.5
H18A—C18—H18C109.5H18D—C18A—H18F109.5
H18B—C18—H18C109.5H18E—C18A—H18F109.5
C16—C15—C14115.6 (2)C16A—C15A—C14A112.0 (2)
C16—C15—H15A108.4C16A—C15A—H15C109.2
C14—C15—H15A108.4C14A—C15A—H15C109.2
C16—C15—H15B108.4C16A—C15A—H15D109.2
C14—C15—H15B108.4C14A—C15A—H15D109.2
H15A—C15—H15B107.4H15C—C15A—H15D107.9
O16—C16—C11122.4 (2)O16A—C16A—C11A121.5 (3)
O16—C16—C15117.1 (2)O16A—C16A—C15A120.1 (3)
C11—C16—C15120.4 (2)C11A—C16A—C15A118.4 (3)
C22—C21—C26117.8 (3)C22A—C21A—C26A118.1 (3)
C22—C21—C1121.1 (2)C22A—C21A—C1A121.2 (3)
C26—C21—C1121.0 (2)C26A—C21A—C1A120.5 (2)
O22—C22—C21123.6 (3)O22A—C22A—C21A123.7 (3)
O22—C22—C23113.4 (2)O22A—C22A—C23A112.3 (3)
C21—C22—C23123.0 (2)C21A—C22A—C23A124.0 (3)
C22—O22—H22113 (3)C22A—O22A—H22A114 (3)
C22—C23—C24114.0 (2)C22A—C23A—C24A114.7 (3)
C22—C23—H23B108.8C22A—C23A—H23C108.6
C24—C23—H23B108.8C24A—C23A—H23C108.6
C22—C23—H23A108.8C22A—C23A—H23D108.6
C24—C23—H23A108.8C24A—C23A—H23D108.6
H23B—C23—H23A107.7H23C—C23A—H23D107.6
C23—C24—C27111.1 (2)C23A—C24A—C25A108.1 (3)
C23—C24—C25107.1 (2)C23A—C24A—C28A110.6 (3)
C27—C24—C25111.1 (2)C25A—C24A—C28A109.8 (3)
C23—C24—C28109.0 (2)C23A—C24A—C27A110.0 (3)
C27—C24—C28109.0 (2)C25A—C24A—C27A109.6 (3)
C25—C24—C28109.6 (2)C28A—C24A—C27A108.8 (3)
C24—C27—H27A109.5C24A—C27A—H27D109.5
C24—C27—H27B109.5C24A—C27A—H27E109.5
H27A—C27—H27B109.5H27D—C27A—H27E109.5
C24—C27—H27C109.5C24A—C27A—H27F109.5
H27A—C27—H27C109.5H27D—C27A—H27F109.5
H27B—C27—H27C109.5H27E—C27A—H27F109.5
C24—C28—H28A109.5C24A—C28A—H28D109.5
C24—C28—H28B109.5C24A—C28A—H28E109.5
H28A—C28—H28B109.5H28D—C28A—H28E109.5
C24—C28—H28C109.5C24A—C28A—H28F109.5
H28A—C28—H28C109.5H28D—C28A—H28F109.5
H28B—C28—H28C109.5H28E—C28A—H28F109.5
C26—C25—C24115.1 (2)C26A—C25A—C24A114.5 (3)
C26—C25—H25A108.5C26A—C25A—H25C108.6
C24—C25—H25A108.5C24A—C25A—H25C108.6
C26—C25—H25B108.5C26A—C25A—H25D108.6
C24—C25—H25B108.5C24A—C25A—H25D108.6
H25A—C25—H25B107.5H25C—C25A—H25D107.6
O26—C26—C21122.4 (2)O26A—C26A—C21A122.0 (3)
O26—C26—C25117.0 (2)O26A—C26A—C25A118.3 (3)
C21—C26—C25120.6 (2)C21A—C26A—C25A119.6 (3)
C36—C31—C32117.9 (3)C32A—C31A—C36A117.6 (3)
C36—C31—C1120.6 (3)C32A—C31A—C1A121.5 (3)
C32—C31—C1121.2 (2)C36A—C31A—C1A120.6 (3)
C33—C32—C31121.2 (3)C33A—C32A—C31A121.8 (3)
C33—C32—H32119.4C33A—C32A—H32A119.1
C31—C32—H32119.4C31A—C32A—H32A119.1
C34—C33—C32118.1 (3)C34A—C33A—C32A118.5 (3)
C34—C33—H33120.9C34A—C33A—H33A120.8
C32—C33—H33120.9C32A—C33A—H33A120.8
C35—C34—F34119.0 (3)F34A—C34A—C33A119.5 (3)
C35—C34—C33122.8 (3)F34A—C34A—C35A118.0 (3)
F34—C34—C33118.2 (3)C33A—C34A—C35A122.5 (3)
C34—C35—C36118.7 (3)C34A—C35A—C36A118.0 (3)
C34—C35—H35120.7C34A—C35A—H35A121.0
C36—C35—H35120.7C36A—C35A—H35A121.0
C35—C36—C31121.2 (3)C35A—C36A—C31A121.6 (3)
C35—C36—H36119.4C35A—C36A—H36A119.2
C31—C36—H36119.4C31A—C36A—H36A119.2
C21—C1—C11—C1285.9 (3)C21A—C1A—C11A—C12A83.0 (3)
C31—C1—C11—C1247.1 (3)C31A—C1A—C11A—C12A51.0 (4)
C21—C1—C11—C1691.1 (3)C21A—C1A—C11A—C16A95.1 (3)
C31—C1—C11—C16135.9 (2)C31A—C1A—C11A—C16A130.8 (3)
C16—C11—C12—O12172.1 (2)C16A—C11A—C12A—O12A176.9 (2)
C1—C11—C12—O124.9 (4)C1A—C11A—C12A—O12A1.2 (4)
C16—C11—C12—C136.9 (4)C16A—C11A—C12A—C13A3.8 (4)
C1—C11—C12—C13176.2 (2)C1A—C11A—C12A—C13A178.1 (3)
O12—C12—C13—C14159.6 (2)O12A—C12A—C13A—C14A159.0 (2)
C11—C12—C13—C1421.3 (4)C11A—C12A—C13A—C14A21.6 (4)
C12—C13—C14—C1546.1 (3)C12A—C13A—C14A—C15A47.0 (3)
C12—C13—C14—C1775.1 (3)C12A—C13A—C14A—C18A167.8 (3)
C12—C13—C14—C18164.4 (2)C12A—C13A—C14A—C17A72.7 (3)
C17—C14—C15—C1674.0 (3)C18A—C14A—C15A—C16A177.2 (3)
C13—C14—C15—C1646.6 (3)C13A—C14A—C15A—C16A57.8 (3)
C18—C14—C15—C16165.4 (2)C17A—C14A—C15A—C16A62.8 (3)
C12—C11—C16—O16169.7 (3)C12A—C11A—C16A—O16A165.5 (3)
C1—C11—C16—O167.5 (4)C1A—C11A—C16A—O16A12.8 (4)
C12—C11—C16—C156.6 (4)C12A—C11A—C16A—C15A14.6 (4)
C1—C11—C16—C15176.2 (2)C1A—C11A—C16A—C15A167.0 (2)
C14—C15—C16—O16161.5 (2)C14A—C15A—C16A—O16A136.7 (3)
C14—C15—C16—C1122.0 (4)C14A—C15A—C16A—C11A43.5 (4)
C11—C1—C21—C2292.0 (3)C11A—C1A—C21A—C22A94.2 (3)
C31—C1—C21—C22134.5 (3)C31A—C1A—C21A—C22A131.7 (3)
C11—C1—C21—C2683.9 (3)C11A—C1A—C21A—C26A81.3 (3)
C31—C1—C21—C2649.5 (3)C31A—C1A—C21A—C26A52.8 (3)
C26—C21—C22—O22169.4 (3)C26A—C21A—C22A—O22A169.5 (3)
C1—C21—C22—O226.6 (4)C1A—C21A—C22A—O22A6.0 (5)
C26—C21—C22—C239.4 (4)C26A—C21A—C22A—C23A10.9 (4)
C1—C21—C22—C23174.5 (2)C1A—C21A—C22A—C23A173.6 (3)
O22—C22—C23—C24158.7 (2)O22A—C22A—C23A—C24A163.9 (3)
C21—C22—C23—C2422.4 (4)C21A—C22A—C23A—C24A15.7 (5)
C22—C23—C24—C2772.1 (3)C22A—C23A—C24A—C25A44.8 (4)
C22—C23—C24—C2549.3 (3)C22A—C23A—C24A—C28A75.5 (4)
C22—C23—C24—C28167.8 (3)C22A—C23A—C24A—C27A164.4 (3)
C23—C24—C25—C2649.0 (3)C23A—C24A—C25A—C26A50.5 (4)
C27—C24—C25—C2672.4 (3)C28A—C24A—C25A—C26A70.3 (4)
C28—C24—C25—C26167.1 (2)C27A—C24A—C25A—C26A170.3 (3)
C22—C21—C26—O26168.1 (2)C22A—C21A—C26A—O26A172.7 (3)
C1—C21—C26—O268.0 (4)C1A—C21A—C26A—O26A2.9 (4)
C22—C21—C26—C2510.1 (4)C22A—C21A—C26A—C25A4.7 (4)
C1—C21—C26—C25173.8 (2)C1A—C21A—C26A—C25A179.7 (3)
C24—C25—C26—O26160.7 (2)C24A—C25A—C26A—O26A155.0 (3)
C24—C25—C26—C2121.1 (3)C24A—C25A—C26A—C21A27.5 (4)
C21—C1—C31—C3629.0 (3)C21A—C1A—C31A—C32A158.2 (3)
C11—C1—C31—C36162.0 (2)C11A—C1A—C31A—C32A24.8 (4)
C21—C1—C31—C32156.8 (2)C21A—C1A—C31A—C36A29.0 (4)
C11—C1—C31—C3223.9 (3)C11A—C1A—C31A—C36A162.4 (3)
C36—C31—C32—C331.7 (4)C36A—C31A—C32A—C33A2.4 (4)
C1—C31—C32—C33176.0 (3)C1A—C31A—C32A—C33A175.5 (3)
C31—C32—C33—C340.8 (5)C31A—C32A—C33A—C34A0.0 (4)
C32—C33—C34—C350.4 (5)C32A—C33A—C34A—F34A177.4 (3)
C32—C33—C34—F34179.5 (3)C32A—C33A—C34A—C35A2.5 (5)
F34—C34—C35—C36179.6 (3)F34A—C34A—C35A—C36A177.6 (3)
C33—C34—C35—C360.5 (5)C33A—C34A—C35A—C36A2.3 (5)
C34—C35—C36—C310.6 (4)C34A—C35A—C36A—C31A0.3 (5)
C32—C31—C36—C351.7 (4)C32A—C31A—C36A—C35A2.6 (4)
C1—C31—C36—C35176.0 (3)C1A—C31A—C36A—C35A175.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12—H12···O260.95 (4)1.68 (4)2.590 (3)161 (4)
O22—H22···O160.85 (4)1.81 (4)2.636 (3)164 (4)
O12A—H12A···O26A0.85 (4)1.77 (4)2.564 (3)154 (3)
O22A—H22A···O16A0.86 (5)1.85 (5)2.701 (4)174 (5)
(II) ; top
Crystal data top
C23H27ClO4F(000) = 856
Mr = 402.90Dx = 1.265 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.892 (1) ÅCell parameters from 4736 reflections
b = 11.813 (1) Åθ = 0–25°
c = 13.351 (1) ŵ = 0.21 mm1
β = 115.78 (1)°T = 173 K
V = 2114.9 (3) Å3Block, colourless
Z = 40.54 × 0.42 × 0.36 mm
Data collection top
Siemens CCD three-circle
diffractometer
4667 independent reflections
Radiation source: fine-focus sealed tube3419 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
ω scansθmax = 27.1°, θmin = 1.5°
Absorption correction: empirical
(SADABS; Sheldrick, 1996)
h = 1919
Tmin = 0.897, Tmax = 0.930k = 1515
39320 measured reflectionsl = 1717
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H 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 reflectionsΔρmax = 0.28 e Å3
262 parametersΔρmin = 0.26 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
C10.22157 (12)0.49071 (13)0.51543 (13)0.0224 (3)
H10.16950.47340.43880.027*
C110.22324 (12)0.62002 (13)0.52160 (13)0.0224 (3)
C120.18504 (12)0.68418 (14)0.42466 (13)0.0235 (3)
O120.15613 (9)0.63941 (10)0.32547 (9)0.0304 (3)
H120.194 (2)0.560 (3)0.326 (2)0.104 (10)*
C130.17651 (13)0.81076 (14)0.42427 (13)0.0270 (4)
H13A0.11390.83360.36030.032*
H13B0.23260.84410.41330.032*
C140.17719 (13)0.86003 (14)0.53093 (14)0.0266 (4)
C170.19335 (16)0.98841 (15)0.53394 (16)0.0394 (5)
H17A0.25531.00460.52770.059*
H17B0.19791.01890.60430.059*
H17C0.13721.02380.47170.059*
C180.07702 (13)0.83623 (16)0.53462 (15)0.0349 (4)
H18A0.02340.87600.47320.052*
H18B0.08010.86290.60560.052*
H18C0.06380.75470.52740.052*
C150.26382 (12)0.80542 (14)0.63046 (13)0.0264 (4)
H15A0.32700.83910.63710.032*
H15B0.25700.82490.69890.032*
C160.27113 (12)0.67821 (14)0.62462 (13)0.0246 (4)
O160.32404 (9)0.62723 (11)0.71576 (9)0.0346 (3)
C210.31697 (12)0.43707 (13)0.51963 (13)0.0235 (3)
C220.39823 (13)0.40510 (14)0.61727 (14)0.0275 (4)
O220.40875 (9)0.43445 (11)0.71632 (9)0.0352 (3)
H220.364 (3)0.516 (3)0.717 (3)0.139 (13)*
C230.48186 (13)0.33348 (15)0.61733 (15)0.0319 (4)
H23A0.50020.27660.67750.038*
H23B0.54070.38250.63500.038*
C240.45819 (13)0.27141 (15)0.50743 (15)0.0302 (4)
C270.55474 (14)0.22635 (18)0.50696 (18)0.0430 (5)
H27A0.53910.18810.43610.065*
H27B0.58650.17260.56830.065*
H27C0.60030.28960.51620.065*
C280.38791 (14)0.17100 (16)0.49155 (17)0.0376 (4)
H28A0.37420.13290.42120.056*
H28B0.32530.19840.49010.056*
H28C0.41940.11760.55320.056*
C250.41011 (13)0.35758 (15)0.41333 (15)0.0310 (4)
H25A0.46170.41200.41620.037*
H25B0.38550.31730.34120.037*
C260.32482 (12)0.42247 (14)0.41790 (14)0.0256 (4)
O260.26248 (9)0.46616 (10)0.32641 (9)0.0298 (3)
C310.18285 (12)0.43268 (14)0.59301 (13)0.0235 (3)
C320.12458 (13)0.48992 (15)0.63529 (15)0.0305 (4)
H320.10880.56740.61700.037*
C330.08902 (13)0.43551 (15)0.70403 (15)0.0316 (4)
H330.04970.47550.73240.038*
C340.11200 (12)0.32298 (15)0.73000 (13)0.0263 (4)
Cl10.07554 (3)0.25460 (4)0.82338 (4)0.03448 (13)
C350.16520 (12)0.26240 (14)0.68544 (13)0.0275 (4)
H350.17810.18410.70130.033*
C360.19970 (13)0.31769 (14)0.61680 (13)0.0269 (4)
H360.23570.27590.58540.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0255 (8)0.0222 (8)0.0190 (8)0.0005 (7)0.0091 (7)0.0004 (6)
C110.0240 (8)0.0220 (8)0.0228 (8)0.0009 (7)0.0118 (7)0.0003 (6)
C120.0242 (8)0.0257 (9)0.0239 (8)0.0021 (7)0.0137 (7)0.0005 (7)
O120.0402 (7)0.0300 (7)0.0205 (6)0.0095 (6)0.0126 (5)0.0012 (5)
C130.0327 (9)0.0253 (9)0.0262 (8)0.0037 (7)0.0157 (7)0.0031 (7)
C140.0312 (9)0.0232 (9)0.0281 (9)0.0013 (7)0.0154 (7)0.0007 (7)
C170.0530 (12)0.0251 (10)0.0410 (11)0.0008 (9)0.0212 (10)0.0026 (8)
C180.0337 (10)0.0403 (11)0.0351 (10)0.0058 (8)0.0191 (8)0.0003 (8)
C150.0285 (9)0.0242 (9)0.0269 (8)0.0015 (7)0.0123 (7)0.0048 (7)
C160.0255 (9)0.0263 (9)0.0238 (8)0.0009 (7)0.0125 (7)0.0005 (7)
O160.0397 (7)0.0330 (7)0.0225 (6)0.0030 (6)0.0056 (5)0.0021 (5)
C210.0256 (8)0.0206 (8)0.0243 (8)0.0016 (7)0.0108 (7)0.0005 (6)
C220.0277 (9)0.0242 (9)0.0299 (9)0.0023 (7)0.0119 (7)0.0018 (7)
O220.0398 (7)0.0379 (7)0.0237 (6)0.0036 (6)0.0098 (5)0.0001 (5)
C230.0270 (9)0.0308 (9)0.0355 (10)0.0020 (7)0.0113 (8)0.0059 (8)
C240.0286 (9)0.0284 (10)0.0382 (10)0.0031 (7)0.0187 (8)0.0038 (8)
C270.0361 (11)0.0459 (12)0.0546 (13)0.0123 (9)0.0268 (10)0.0110 (10)
C280.0406 (11)0.0293 (10)0.0501 (12)0.0009 (8)0.0264 (10)0.0006 (9)
C250.0357 (10)0.0289 (9)0.0351 (10)0.0037 (8)0.0217 (8)0.0037 (8)
C260.0288 (9)0.0198 (8)0.0297 (9)0.0025 (7)0.0141 (7)0.0007 (7)
O260.0398 (7)0.0268 (6)0.0237 (6)0.0062 (5)0.0146 (5)0.0008 (5)
C310.0249 (8)0.0243 (9)0.0213 (8)0.0004 (7)0.0100 (7)0.0002 (6)
C320.0357 (10)0.0222 (9)0.0390 (10)0.0048 (7)0.0213 (9)0.0056 (7)
C330.0360 (10)0.0289 (9)0.0389 (10)0.0039 (8)0.0248 (8)0.0007 (8)
C340.0283 (9)0.0295 (9)0.0231 (8)0.0037 (7)0.0129 (7)0.0018 (7)
Cl10.0396 (3)0.0374 (3)0.0340 (2)0.0007 (2)0.0231 (2)0.00790 (19)
C350.0342 (9)0.0210 (9)0.0292 (9)0.0011 (7)0.0156 (8)0.0030 (7)
C360.0330 (9)0.0245 (9)0.0276 (9)0.0026 (7)0.0172 (7)0.0002 (7)
Geometric parameters (Å, º) top
C1—C111.529 (2)C22—C231.505 (2)
C1—C211.534 (2)O22—H221.17 (4)
C1—C311.547 (2)C23—C241.538 (2)
C1—H11.0000C23—H23A0.9900
C11—C121.390 (2)C23—H23B0.9900
C11—C161.421 (2)C24—C251.531 (2)
C12—O121.3125 (19)C24—C281.534 (2)
C12—C131.500 (2)C24—C271.536 (2)
O12—H121.09 (3)C27—H27A0.9800
C13—C141.534 (2)C27—H27B0.9800
C13—H13A0.9900C27—H27C0.9800
C13—H13B0.9900C28—H28A0.9800
C14—C171.533 (2)C28—H28B0.9800
C14—C151.535 (2)C28—H28C0.9800
C14—C181.540 (2)C25—C261.507 (2)
C17—H17A0.9800C25—H25A0.9900
C17—H17B0.9800C25—H25B0.9900
C17—H17C0.9800C26—O261.278 (2)
C18—H18A0.9800C31—C361.393 (2)
C18—H18B0.9800C31—C321.398 (2)
C18—H18C0.9800C32—C331.399 (2)
C15—C161.511 (2)C32—H320.9500
C15—H15A0.9900C33—C341.379 (2)
C15—H15B0.9900C33—H330.9500
C16—O161.2768 (19)C34—C351.380 (2)
O16—H221.44 (4)C34—Cl11.7579 (16)
C21—C221.391 (2)C35—C361.393 (2)
C21—C261.424 (2)C35—H350.9500
C22—O221.309 (2)C36—H360.9500
C11—C1—C21114.68 (13)C22—O22—H22113.9 (17)
C11—C1—C31114.11 (13)C22—C23—C24114.91 (14)
C21—C1—C31113.66 (13)C22—C23—H23A108.5
C11—C1—H1104.3C24—C23—H23A108.5
C21—C1—H1104.3C22—C23—H23B108.5
C31—C1—H1104.3C24—C23—H23B108.5
C12—C11—C16117.85 (15)H23A—C23—H23B107.5
C12—C11—C1120.26 (14)C25—C24—C28110.67 (15)
C16—C11—C1121.65 (14)C25—C24—C27109.37 (14)
O12—C12—C11122.78 (15)C28—C24—C27108.36 (15)
O12—C12—C13114.08 (14)C25—C24—C23107.29 (14)
C11—C12—C13123.11 (14)C28—C24—C23111.10 (14)
C12—O12—H12113.1 (15)C27—C24—C23110.04 (15)
C12—C13—C14114.11 (13)C24—C27—H27A109.5
C12—C13—H13A108.7C24—C27—H27B109.5
C14—C13—H13A108.7H27A—C27—H27B109.5
C12—C13—H13B108.7C24—C27—H27C109.5
C14—C13—H13B108.7H27A—C27—H27C109.5
H13A—C13—H13B107.6H27B—C27—H27C109.5
C17—C14—C13109.70 (14)C24—C28—H28A109.5
C17—C14—C15109.26 (15)C24—C28—H28B109.5
C13—C14—C15107.94 (13)H28A—C28—H28B109.5
C17—C14—C18108.84 (15)C24—C28—H28C109.5
C13—C14—C18110.18 (14)H28A—C28—H28C109.5
C15—C14—C18110.90 (14)H28B—C28—H28C109.5
C14—C17—H17A109.5C26—C25—C24113.98 (14)
C14—C17—H17B109.5C26—C25—H25A108.8
H17A—C17—H17B109.5C24—C25—H25A108.8
C14—C17—H17C109.5C26—C25—H25B108.8
H17A—C17—H17C109.5C24—C25—H25B108.8
H17B—C17—H17C109.5H25A—C25—H25B107.7
C14—C18—H18A109.5O26—C26—C21122.40 (15)
C14—C18—H18B109.5O26—C26—C25116.19 (14)
H18A—C18—H18B109.5C21—C26—C25121.37 (15)
C14—C18—H18C109.5C36—C31—C32117.48 (15)
H18A—C18—H18C109.5C36—C31—C1120.14 (14)
H18B—C18—H18C109.5C32—C31—C1122.23 (14)
C16—C15—C14115.19 (14)C31—C32—C33121.39 (16)
C16—C15—H15A108.5C31—C32—H32119.3
C14—C15—H15A108.5C33—C32—H32119.3
C16—C15—H15B108.5C34—C33—C32118.97 (16)
C14—C15—H15B108.5C34—C33—H33120.5
H15A—C15—H15B107.5C32—C33—H33120.5
O16—C16—C11122.42 (15)C33—C34—C35121.19 (15)
O16—C16—C15116.64 (14)C33—C34—Cl1120.13 (13)
C11—C16—C15120.92 (14)C35—C34—Cl1118.67 (13)
C16—O16—H22121.4 (14)C34—C35—C36119.06 (16)
C22—C21—C26117.54 (15)C34—C35—H35120.5
C22—C21—C1124.12 (14)C36—C35—H35120.5
C26—C21—C1118.31 (14)C35—C36—C31121.74 (15)
O22—C22—C21123.23 (16)C35—C36—H36119.1
O22—C22—C23114.39 (15)C31—C36—H36119.1
C21—C22—C23122.38 (15)
C21—C1—C11—C1293.38 (18)C1—C21—C22—C23168.27 (15)
C31—C1—C11—C12133.04 (15)O22—C22—C23—C24163.84 (15)
C21—C1—C11—C1680.95 (18)C21—C22—C23—C2416.2 (2)
C31—C1—C11—C1652.6 (2)C22—C23—C24—C2546.98 (19)
C16—C11—C12—O12167.15 (15)C22—C23—C24—C2874.11 (19)
C1—C11—C12—O127.4 (2)C22—C23—C24—C27165.88 (15)
C16—C11—C12—C1310.7 (2)C28—C24—C25—C2670.82 (19)
C1—C11—C12—C13174.80 (15)C27—C24—C25—C26169.87 (16)
O12—C12—C13—C14161.32 (14)C23—C24—C25—C2650.54 (19)
C11—C12—C13—C1420.7 (2)C22—C21—C26—O26167.85 (15)
C12—C13—C14—C17166.55 (15)C1—C21—C26—O2610.0 (2)
C12—C13—C14—C1547.59 (19)C22—C21—C26—C259.9 (2)
C12—C13—C14—C1873.64 (19)C1—C21—C26—C25172.30 (14)
C17—C14—C15—C16166.47 (14)C24—C25—C26—O26157.81 (15)
C13—C14—C15—C1647.23 (19)C24—C25—C26—C2124.3 (2)
C18—C14—C15—C1673.56 (18)C11—C1—C31—C36164.24 (15)
C12—C11—C16—O16166.91 (15)C21—C1—C31—C3630.2 (2)
C1—C11—C16—O167.6 (2)C11—C1—C31—C3220.3 (2)
C12—C11—C16—C1511.3 (2)C21—C1—C31—C32154.34 (15)
C1—C11—C16—C15174.20 (14)C36—C31—C32—C333.5 (3)
C14—C15—C16—O16162.32 (14)C1—C31—C32—C33179.05 (16)
C14—C15—C16—C1119.3 (2)C31—C32—C33—C340.2 (3)
C11—C1—C21—C2289.96 (19)C32—C33—C34—C353.0 (3)
C31—C1—C21—C2243.8 (2)C32—C33—C34—Cl1175.81 (14)
C11—C1—C21—C2687.73 (18)C33—C34—C35—C362.7 (3)
C31—C1—C21—C26138.48 (15)Cl1—C34—C35—C36176.08 (13)
C26—C21—C22—O22165.88 (15)C34—C35—C36—C310.7 (3)
C1—C21—C22—O2211.8 (3)C32—C31—C36—C353.7 (2)
C26—C21—C22—C2314.0 (2)C1—C31—C36—C35179.42 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12—H12···O261.09 (3)1.50 (3)2.5845 (16)169 (3)
O22—H22···O161.17 (4)1.44 (4)2.6018 (18)169 (3)
(III) ; top
Crystal data top
C23H28O5F(000) = 824
Mr = 384.45Dx = 1.281 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.736 (2) ÅCell parameters from 3615 reflections
b = 11.370 (3) Åθ = 0–25°
c = 18.263 (3) ŵ = 0.09 mm1
β = 99.54 (1)°T = 173 K
V = 1993.7 (7) Å3Plate, colourless
Z = 40.50 × 0.20 × 0.10 mm
Data collection top
Siemens CCD three-circle
diffractometer
4076 independent reflections
Radiation source: fine-focus sealed tube1722 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.090
ω scansθmax = 26.4°, θmin = 2.1°
Absorption correction: empirical
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.957, Tmax = 0.991k = 1412
16535 measured reflectionsl = 2222
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.079H 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 reflectionsΔρmax = 0.32 e Å3
266 parametersΔρmin = 0.30 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
C10.9184 (4)0.4382 (3)0.73274 (19)0.0452 (10)
H10.89370.36320.75610.054*
C111.0160 (4)0.4988 (3)0.79535 (19)0.0463 (10)
C121.0173 (4)0.4676 (4)0.8689 (2)0.0481 (10)
O120.9297 (3)0.3920 (3)0.89048 (15)0.0602 (8)
H120.841 (6)0.370 (5)0.851 (3)0.13 (2)*
C131.1160 (4)0.5223 (4)0.9314 (2)0.0558 (11)
H13A1.13730.46430.97210.067*
H13B1.06960.59030.95080.067*
C141.2527 (4)0.5638 (4)0.9091 (2)0.0512 (11)
C171.3337 (5)0.6372 (4)0.9727 (2)0.0655 (13)
H17A1.42130.66430.95880.098*
H17B1.35370.58881.01760.098*
H17C1.27760.70530.98230.098*
C181.3412 (4)0.4584 (4)0.8939 (2)0.0586 (12)
H18A1.42790.48620.87920.088*
H18B1.28940.41070.85390.088*
H18C1.36300.41050.93900.088*
C151.2150 (4)0.6407 (3)0.8396 (2)0.0502 (10)
H15A1.18430.71860.85510.060*
H15B1.30020.65320.81760.060*
C161.1035 (4)0.5924 (3)0.7806 (2)0.0460 (10)
O161.0913 (3)0.6418 (2)0.71696 (14)0.0516 (7)
C210.7771 (4)0.4986 (3)0.7100 (2)0.0466 (10)
C220.7518 (4)0.5907 (3)0.6611 (2)0.0448 (10)
O220.8508 (3)0.6511 (2)0.63541 (14)0.0494 (7)
H220.947 (8)0.646 (6)0.658 (4)0.18 (3)*
C230.6063 (4)0.6315 (4)0.6307 (2)0.0500 (10)
H23A0.59990.64740.57690.060*
H23B0.58850.70640.65520.060*
C240.4936 (4)0.5433 (4)0.6417 (2)0.0559 (11)
C270.3496 (4)0.5988 (4)0.6197 (2)0.0621 (12)
H27A0.27780.54170.62720.093*
H27B0.33640.62200.56730.093*
H27C0.34220.66840.65050.093*
C280.5010 (5)0.4316 (4)0.5935 (2)0.0686 (13)
H28A0.42800.37620.60190.103*
H28B0.59240.39430.60720.103*
H28C0.48710.45370.54090.103*
C250.5200 (4)0.5064 (4)0.7225 (2)0.0587 (11)
H25A0.50620.57490.75390.070*
H25B0.45150.44530.73050.070*
C260.6656 (4)0.4586 (4)0.7460 (2)0.0568 (11)
O260.6842 (3)0.3879 (3)0.80061 (16)0.0675 (9)
C310.9942 (4)0.3961 (3)0.67046 (19)0.0446 (10)
C321.1154 (4)0.3284 (3)0.6893 (2)0.0494 (10)
H321.15180.31710.74040.059*
C331.1841 (4)0.2775 (3)0.6372 (2)0.0488 (10)
H331.26430.23030.65240.059*
C341.1349 (4)0.2959 (3)0.5616 (2)0.0479 (10)
O341.2091 (3)0.2491 (2)0.51111 (15)0.0568 (8)
H341.160 (6)0.275 (5)0.455 (3)0.118 (18)*
C351.0126 (4)0.3602 (3)0.5412 (2)0.0476 (10)
H350.97600.37100.49010.057*
C360.9439 (4)0.4085 (3)0.5948 (2)0.0465 (10)
H360.86020.45130.57950.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.045 (2)0.053 (3)0.036 (2)0.0016 (19)0.0030 (17)0.0063 (18)
C110.049 (2)0.051 (3)0.039 (2)0.001 (2)0.0056 (18)0.0001 (18)
C120.051 (2)0.051 (3)0.043 (2)0.004 (2)0.0115 (19)0.0030 (19)
O120.0629 (19)0.075 (2)0.0432 (16)0.0116 (17)0.0087 (14)0.0075 (15)
C130.062 (3)0.060 (3)0.044 (2)0.006 (2)0.0023 (19)0.004 (2)
C140.054 (2)0.056 (3)0.041 (2)0.001 (2)0.0017 (18)0.0011 (19)
C170.068 (3)0.069 (3)0.053 (3)0.002 (2)0.009 (2)0.007 (2)
C180.060 (3)0.060 (3)0.055 (3)0.009 (2)0.006 (2)0.002 (2)
C150.051 (2)0.049 (2)0.047 (2)0.003 (2)0.0043 (18)0.0013 (19)
C160.048 (2)0.051 (3)0.040 (2)0.004 (2)0.0070 (18)0.0022 (19)
O160.0551 (16)0.0552 (17)0.0429 (16)0.0010 (13)0.0036 (12)0.0035 (13)
C210.046 (2)0.044 (2)0.048 (2)0.0019 (19)0.0056 (18)0.0049 (19)
C220.050 (2)0.046 (2)0.040 (2)0.003 (2)0.0094 (18)0.0020 (18)
O220.0519 (17)0.0514 (17)0.0446 (15)0.0032 (14)0.0068 (13)0.0060 (13)
C230.049 (2)0.056 (3)0.044 (2)0.001 (2)0.0039 (18)0.0037 (19)
C240.051 (2)0.061 (3)0.055 (2)0.003 (2)0.006 (2)0.005 (2)
C270.041 (2)0.079 (3)0.067 (3)0.002 (2)0.013 (2)0.006 (2)
C280.073 (3)0.069 (3)0.063 (3)0.005 (3)0.008 (2)0.000 (2)
C250.055 (3)0.065 (3)0.058 (3)0.000 (2)0.016 (2)0.000 (2)
C260.061 (3)0.057 (3)0.054 (3)0.003 (2)0.018 (2)0.007 (2)
O260.0552 (18)0.083 (2)0.066 (2)0.0026 (16)0.0157 (15)0.0276 (17)
C310.046 (2)0.048 (2)0.038 (2)0.0074 (19)0.0026 (17)0.0017 (17)
C320.050 (2)0.056 (3)0.040 (2)0.002 (2)0.0001 (18)0.0019 (19)
C330.051 (2)0.053 (3)0.042 (2)0.002 (2)0.0065 (19)0.0001 (19)
C340.057 (3)0.044 (2)0.043 (2)0.008 (2)0.010 (2)0.0037 (19)
O340.0608 (18)0.0631 (19)0.0474 (17)0.0014 (15)0.0118 (14)0.0064 (14)
C350.053 (2)0.051 (3)0.039 (2)0.004 (2)0.0083 (18)0.0046 (19)
C360.051 (2)0.045 (2)0.043 (2)0.0048 (19)0.0054 (18)0.0009 (18)
Geometric parameters (Å, º) top
C1—C111.525 (5)O22—H220.96 (7)
C1—C211.532 (5)C23—C241.523 (5)
C1—C311.531 (5)C23—H23A0.9900
C1—H11.0000C23—H23B0.9900
C11—C121.388 (5)C24—C251.515 (6)
C11—C161.417 (5)C24—C271.530 (5)
C12—O121.316 (5)C24—C281.554 (6)
C12—C131.500 (5)C27—H27A0.9800
O12—H121.06 (6)C27—H27B0.9800
C13—C141.529 (5)C27—H27C0.9800
C13—H13A0.9900C28—H28A0.9800
C13—H13B0.9900C28—H28B0.9800
C14—C181.529 (5)C28—H28C0.9800
C14—C151.535 (5)C25—C261.512 (6)
C14—C171.537 (5)C25—H25A0.9900
C17—H17A0.9800C25—H25B0.9900
C17—H17B0.9800C26—O261.271 (4)
C17—H17C0.9800C31—C361.395 (5)
C18—H18A0.9800C31—C321.404 (5)
C18—H18B0.9800C32—C331.378 (5)
C18—H18C0.9800C32—H320.9500
C15—C161.501 (5)C33—C341.400 (5)
C15—H15A0.9900C33—H330.9500
C15—H15B0.9900C34—O341.369 (4)
C16—O161.278 (4)C34—C351.394 (5)
C21—C221.372 (5)O34—H341.09 (6)
C21—C261.433 (5)C35—C361.387 (5)
C22—O221.331 (4)C35—H350.9500
C22—C231.507 (5)C36—H360.9500
C11—C1—C21114.9 (3)C22—C23—C24113.7 (3)
C11—C1—C31112.4 (3)C22—C23—H23A108.8
C21—C1—C31117.4 (3)C24—C23—H23A108.8
C11—C1—H1103.3C22—C23—H23B108.8
C21—C1—H1103.3C24—C23—H23B108.8
C31—C1—H1103.3H23A—C23—H23B107.7
C12—C11—C16117.8 (3)C25—C24—C23107.6 (3)
C12—C11—C1121.0 (4)C25—C24—C27111.7 (3)
C16—C11—C1121.1 (3)C23—C24—C27110.0 (3)
O12—C12—C11123.6 (4)C25—C24—C28108.0 (3)
O12—C12—C13114.1 (3)C23—C24—C28111.2 (3)
C11—C12—C13122.2 (4)C27—C24—C28108.3 (3)
C12—O12—H12116 (3)C24—C27—H27A109.5
C12—C13—C14113.7 (3)C24—C27—H27B109.5
C12—C13—H13A108.8H27A—C27—H27B109.5
C14—C13—H13A108.8C24—C27—H27C109.5
C12—C13—H13B108.8H27A—C27—H27C109.5
C14—C13—H13B108.8H27B—C27—H27C109.5
H13A—C13—H13B107.7C24—C28—H28A109.5
C18—C14—C13110.3 (3)C24—C28—H28B109.5
C18—C14—C15111.2 (3)H28A—C28—H28B109.5
C13—C14—C15107.3 (3)C24—C28—H28C109.5
C18—C14—C17109.2 (3)H28A—C28—H28C109.5
C13—C14—C17109.0 (3)H28B—C28—H28C109.5
C15—C14—C17109.8 (3)C26—C25—C24112.0 (3)
C14—C17—H17A109.5C26—C25—H25A109.2
C14—C17—H17B109.5C24—C25—H25A109.2
H17A—C17—H17B109.5C26—C25—H25B109.2
C14—C17—H17C109.5C24—C25—H25B109.2
H17A—C17—H17C109.5H25A—C25—H25B107.9
H17B—C17—H17C109.5O26—C26—C21122.7 (4)
C14—C18—H18A109.5O26—C26—C25117.1 (4)
C14—C18—H18B109.5C21—C26—C25120.1 (4)
H18A—C18—H18B109.5C36—C31—C32116.2 (3)
C14—C18—H18C109.5C36—C31—C1124.8 (3)
H18A—C18—H18C109.5C32—C31—C1118.6 (3)
H18B—C18—H18C109.5C33—C32—C31123.1 (4)
C16—C15—C14115.5 (3)C33—C32—H32118.5
C16—C15—H15A108.4C31—C32—H32118.5
C14—C15—H15A108.4C32—C33—C34119.5 (4)
C16—C15—H15B108.4C32—C33—H33120.3
C14—C15—H15B108.4C34—C33—H33120.3
H15A—C15—H15B107.5O34—C34—C35123.2 (3)
O16—C16—C11122.3 (3)O34—C34—C33118.2 (4)
O16—C16—C15116.1 (3)C35—C34—C33118.6 (4)
C11—C16—C15121.6 (3)C34—O34—H34109 (3)
C22—C21—C26118.2 (4)C36—C35—C34120.7 (4)
C22—C21—C1125.1 (3)C36—C35—H35119.6
C26—C21—C1116.6 (3)C34—C35—H35119.6
O22—C22—C21124.1 (3)C35—C36—C31121.8 (4)
O22—C22—C23113.8 (3)C35—C36—H36119.1
C21—C22—C23122.1 (4)C31—C36—H36119.1
C22—O22—H22122 (4)
C21—C1—C11—C1291.8 (4)C1—C21—C22—C23168.7 (3)
C31—C1—C11—C12130.5 (4)O22—C22—C23—C24163.5 (3)
C21—C1—C11—C1685.2 (4)C21—C22—C23—C2415.8 (5)
C31—C1—C11—C1652.5 (5)C22—C23—C24—C2549.8 (4)
C16—C11—C12—O12171.8 (3)C22—C23—C24—C27171.7 (3)
C1—C11—C12—O125.3 (6)C22—C23—C24—C2868.2 (4)
C16—C11—C12—C135.4 (6)C23—C24—C25—C2655.5 (5)
C1—C11—C12—C13177.5 (3)C27—C24—C25—C26176.3 (4)
O12—C12—C13—C14154.2 (3)C28—C24—C25—C2664.7 (5)
C11—C12—C13—C1428.4 (5)C22—C21—C26—O26168.1 (4)
C12—C13—C14—C1870.0 (4)C1—C21—C26—O268.8 (6)
C12—C13—C14—C1551.2 (4)C22—C21—C26—C258.0 (6)
C12—C13—C14—C17170.1 (3)C1—C21—C26—C25175.0 (3)
C18—C14—C15—C1675.5 (4)C24—C25—C26—O26155.1 (4)
C13—C14—C15—C1645.2 (5)C24—C25—C26—C2128.5 (6)
C17—C14—C15—C16163.6 (3)C11—C1—C31—C36136.7 (4)
C12—C11—C16—O16166.8 (3)C21—C1—C31—C360.2 (5)
C1—C11—C16—O1610.3 (6)C11—C1—C31—C3250.9 (4)
C12—C11—C16—C1512.3 (6)C21—C1—C31—C32172.6 (3)
C1—C11—C16—C15170.7 (3)C36—C31—C32—C331.0 (6)
C14—C15—C16—O16165.8 (3)C1—C31—C32—C33174.0 (4)
C14—C15—C16—C1115.1 (5)C31—C32—C33—C341.9 (6)
C11—C1—C21—C2284.1 (5)C32—C33—C34—O34176.9 (3)
C31—C1—C21—C2251.4 (5)C32—C33—C34—C353.5 (6)
C11—C1—C21—C2692.6 (4)O34—C34—C35—C36178.1 (3)
C31—C1—C21—C26131.9 (4)C33—C34—C35—C362.3 (6)
C26—C21—C22—O22166.2 (3)C34—C35—C36—C310.6 (6)
C1—C21—C22—O2210.5 (6)C32—C31—C36—C352.2 (6)
C26—C21—C22—C2314.7 (6)C1—C31—C36—C35174.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12—H12···O261.06 (6)1.66 (6)2.667 (4)157 (5)
O22—H22···O160.96 (7)1.62 (7)2.561 (4)165 (6)
O34—H34···O22i1.09 (6)1.84 (5)2.876 (4)156 (4)
Symmetry code: (i) x+2, y+1, z+1.
(IV) ; top
Crystal data top
C24H30O4F(000) = 824
Mr = 382.48Dx = 1.195 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.339 (1) ÅCell parameters from 8192 reflections
b = 11.638 (1) Åθ = 0–25°
c = 20.052 (1) ŵ = 0.08 mm1
β = 102.65 (1)°T = 173 K
V = 2126.5 (3) Å3Block, colourless
Z = 40.70 × 0.45 × 0.30 mm
Data collection top
Siemens CCD three-circle
diffractometer
4868 independent reflections
Radiation source: fine-focus sealed tube3895 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: empirical
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.946, Tmax = 0.976k = 1515
40291 measured reflectionsl = 2626
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H 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 reflectionsΔρmax = 0.24 e Å3
263 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
C10.60824 (14)0.47467 (11)0.26351 (6)0.0268 (3)
H10.63730.40110.24430.032*
C110.50206 (14)0.52913 (11)0.20301 (6)0.0272 (3)
C120.50253 (15)0.50010 (12)0.13691 (7)0.0338 (3)
O120.60208 (13)0.43132 (10)0.11881 (5)0.0473 (3)
H120.689 (2)0.4208 (19)0.1560 (11)0.075 (6)*
C130.39239 (17)0.54470 (14)0.07648 (7)0.0409 (3)
H13A0.37180.48400.04110.049*
H13B0.43560.61090.05690.049*
C140.24776 (15)0.58229 (12)0.09359 (7)0.0363 (3)
C170.15563 (19)0.64889 (15)0.03282 (8)0.0524 (4)
H17A0.06310.67310.04390.079*
H17B0.13490.59920.00760.079*
H17C0.21020.71670.02350.079*
C180.16079 (18)0.47746 (14)0.10892 (8)0.0469 (4)
H18A0.06840.50300.11970.070*
H18B0.21870.43550.14800.070*
H18C0.13960.42700.06890.070*
C150.28560 (15)0.66223 (11)0.15556 (7)0.0333 (3)
H15A0.31770.73700.14030.040*
H15B0.19520.67620.17250.040*
C160.40305 (13)0.61902 (11)0.21420 (6)0.0268 (3)
O160.41477 (10)0.66590 (8)0.27109 (4)0.0305 (2)
C210.75331 (14)0.53822 (11)0.28643 (6)0.0275 (3)
C220.77700 (14)0.63360 (11)0.32751 (6)0.0272 (3)
O220.67166 (10)0.69154 (8)0.34823 (5)0.0315 (2)
H220.573 (2)0.6717 (17)0.3213 (10)0.064 (6)*
C230.92669 (14)0.68318 (11)0.35539 (7)0.0322 (3)
H23A0.93110.71140.40240.039*
H23B0.94140.75000.32710.039*
C241.05194 (14)0.59730 (12)0.35704 (6)0.0310 (3)
C271.19970 (15)0.65904 (14)0.37372 (7)0.0401 (3)
H27A1.20160.71860.33940.060*
H27B1.27860.60360.37350.060*
H27C1.21380.69460.41900.060*
C281.05078 (17)0.50375 (14)0.41084 (8)0.0450 (4)
H28A1.06640.53900.45620.067*
H28B1.12940.44830.40990.067*
H28C0.95590.46410.40070.067*
C251.02709 (15)0.54452 (12)0.28540 (7)0.0350 (3)
H25A1.04580.60410.25310.042*
H25B1.09960.48220.28600.042*
C260.87530 (15)0.49629 (12)0.25914 (7)0.0332 (3)
O260.85754 (12)0.42344 (10)0.21240 (6)0.0476 (3)
C310.53302 (14)0.43480 (10)0.32060 (6)0.0276 (3)
C320.40599 (15)0.36826 (11)0.30212 (7)0.0317 (3)
H320.36120.35900.25510.038*
C330.34367 (16)0.31524 (12)0.35114 (8)0.0376 (3)
H330.25790.26980.33690.045*
C340.40495 (17)0.32753 (12)0.42086 (7)0.0399 (3)
C3410.3387 (2)0.26899 (16)0.47453 (9)0.0578 (5)
H34A0.41730.24360.51240.087*
H34B0.28100.20240.45420.087*
H34C0.27480.32320.49160.087*
C350.52969 (17)0.39499 (12)0.43914 (7)0.0387 (3)
H350.57280.40580.48620.046*
C360.59364 (16)0.44738 (11)0.39024 (7)0.0333 (3)
H360.67980.49230.40460.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0329 (6)0.0228 (6)0.0250 (6)0.0030 (5)0.0067 (5)0.0026 (5)
C110.0307 (6)0.0262 (6)0.0239 (6)0.0040 (5)0.0042 (5)0.0002 (5)
C120.0393 (7)0.0339 (7)0.0281 (6)0.0068 (6)0.0073 (5)0.0043 (5)
O120.0530 (7)0.0578 (7)0.0316 (5)0.0050 (5)0.0103 (5)0.0147 (5)
C130.0509 (9)0.0461 (8)0.0232 (6)0.0116 (7)0.0030 (6)0.0008 (6)
C140.0393 (7)0.0354 (7)0.0290 (6)0.0121 (6)0.0035 (5)0.0062 (5)
C170.0557 (10)0.0526 (10)0.0383 (8)0.0136 (8)0.0128 (7)0.0122 (7)
C180.0482 (9)0.0412 (8)0.0444 (8)0.0207 (7)0.0048 (7)0.0062 (7)
C150.0328 (7)0.0294 (6)0.0336 (7)0.0048 (5)0.0013 (5)0.0067 (5)
C160.0287 (6)0.0249 (6)0.0267 (6)0.0060 (5)0.0055 (5)0.0038 (5)
O160.0311 (5)0.0317 (5)0.0284 (5)0.0040 (4)0.0057 (4)0.0005 (4)
C210.0303 (6)0.0262 (6)0.0255 (6)0.0038 (5)0.0049 (5)0.0004 (5)
C220.0315 (6)0.0254 (6)0.0241 (6)0.0056 (5)0.0048 (5)0.0005 (5)
O220.0301 (5)0.0290 (5)0.0339 (5)0.0071 (4)0.0042 (4)0.0062 (4)
C230.0317 (7)0.0303 (7)0.0333 (7)0.0036 (5)0.0044 (5)0.0056 (5)
C240.0303 (6)0.0351 (7)0.0280 (6)0.0061 (5)0.0073 (5)0.0004 (5)
C270.0324 (7)0.0525 (9)0.0348 (7)0.0017 (6)0.0061 (6)0.0052 (6)
C280.0404 (8)0.0543 (9)0.0416 (8)0.0139 (7)0.0118 (6)0.0151 (7)
C250.0329 (7)0.0409 (7)0.0332 (7)0.0030 (6)0.0114 (5)0.0050 (6)
C260.0382 (7)0.0317 (7)0.0305 (6)0.0036 (6)0.0096 (5)0.0047 (5)
O260.0427 (6)0.0516 (7)0.0508 (6)0.0006 (5)0.0157 (5)0.0259 (5)
C310.0351 (7)0.0212 (6)0.0270 (6)0.0081 (5)0.0077 (5)0.0020 (5)
C320.0371 (7)0.0265 (6)0.0319 (6)0.0056 (5)0.0082 (5)0.0034 (5)
C330.0399 (8)0.0303 (7)0.0457 (8)0.0063 (6)0.0161 (6)0.0078 (6)
C340.0516 (9)0.0328 (7)0.0408 (8)0.0186 (6)0.0220 (7)0.0131 (6)
C3410.0710 (12)0.0565 (10)0.0562 (10)0.0224 (9)0.0359 (9)0.0259 (8)
C350.0561 (9)0.0336 (7)0.0279 (6)0.0172 (7)0.0123 (6)0.0052 (5)
C360.0429 (8)0.0280 (6)0.0283 (6)0.0079 (6)0.0062 (5)0.0012 (5)
Geometric parameters (Å, º) top
C1—C211.5234 (18)C23—C241.5334 (18)
C1—C111.5263 (17)C23—H23A0.9900
C1—C311.5401 (17)C23—H23B0.9900
C1—H11.0000C24—C271.526 (2)
C11—C121.3688 (17)C24—C251.5326 (18)
C11—C161.4460 (18)C24—C281.5345 (19)
C12—O121.3358 (18)C27—H27A0.9800
C12—C131.500 (2)C27—H27B0.9800
O12—H120.98 (2)C27—H27C0.9800
C13—C141.529 (2)C28—H28A0.9800
C13—H13A0.9900C28—H28B0.9800
C13—H13B0.9900C28—H28C0.9800
C14—C151.5303 (19)C25—C261.5082 (19)
C14—C181.5336 (19)C25—H25A0.9900
C14—C171.5385 (19)C25—H25B0.9900
C17—H17A0.9800C26—O261.2476 (16)
C17—H17B0.9800C31—C361.3948 (18)
C17—H17C0.9800C31—C321.3971 (19)
C18—H18A0.9800C32—C331.3914 (19)
C18—H18B0.9800C32—H320.9500
C18—H18C0.9800C33—C341.397 (2)
C15—C161.5079 (17)C33—H330.9500
C15—H15A0.9900C34—C351.386 (2)
C15—H15B0.9900C34—C3411.516 (2)
C16—O161.2475 (15)C341—H34A0.9800
C21—C221.3712 (17)C341—H34B0.9800
C21—C261.4520 (18)C341—H34C0.9800
C22—O221.3320 (15)C35—C361.395 (2)
C22—C231.5025 (18)C35—H350.9500
O22—H220.99 (2)C36—H360.9500
C21—C1—C11114.73 (10)C24—C23—H23A108.8
C21—C1—C31116.25 (10)C22—C23—H23B108.8
C11—C1—C31113.15 (10)C24—C23—H23B108.8
C21—C1—H1103.5H23A—C23—H23B107.7
C11—C1—H1103.5C27—C24—C25109.76 (11)
C31—C1—H1103.5C27—C24—C23110.28 (11)
C12—C11—C16117.81 (12)C25—C24—C23106.43 (11)
C12—C11—C1121.86 (12)C27—C24—C28108.97 (12)
C16—C11—C1120.22 (10)C25—C24—C28110.58 (12)
O12—C12—C11124.12 (13)C23—C24—C28110.78 (11)
O12—C12—C13112.52 (12)C24—C27—H27A109.5
C11—C12—C13123.35 (13)C24—C27—H27B109.5
C12—O12—H12112.1 (12)H27A—C27—H27B109.5
C12—C13—C14113.65 (11)C24—C27—H27C109.5
C12—C13—H13A108.8H27A—C27—H27C109.5
C14—C13—H13A108.8H27B—C27—H27C109.5
C12—C13—H13B108.8C24—C28—H28A109.5
C14—C13—H13B108.8C24—C28—H28B109.5
H13A—C13—H13B107.7H28A—C28—H28B109.5
C13—C14—C15107.34 (11)C24—C28—H28C109.5
C13—C14—C18110.50 (13)H28A—C28—H28C109.5
C15—C14—C18111.05 (12)H28B—C28—H28C109.5
C13—C14—C17109.56 (13)C26—C25—C24114.47 (11)
C15—C14—C17109.06 (12)C26—C25—H25A108.6
C18—C14—C17109.30 (12)C24—C25—H25A108.6
C14—C17—H17A109.5C26—C25—H25B108.6
C14—C17—H17B109.5C24—C25—H25B108.6
H17A—C17—H17B109.5H25A—C25—H25B107.6
C14—C17—H17C109.5O26—C26—C21121.68 (13)
H17A—C17—H17C109.5O26—C26—C25118.38 (12)
H17B—C17—H17C109.5C21—C26—C25119.90 (11)
C14—C18—H18A109.5C36—C31—C32117.30 (12)
C14—C18—H18B109.5C36—C31—C1124.15 (12)
H18A—C18—H18B109.5C32—C31—C1117.96 (11)
C14—C18—H18C109.5C33—C32—C31121.38 (13)
H18A—C18—H18C109.5C33—C32—H32119.3
H18B—C18—H18C109.5C31—C32—H32119.3
C16—C15—C14115.44 (11)C32—C33—C34121.23 (14)
C16—C15—H15A108.4C32—C33—H33119.4
C14—C15—H15A108.4C34—C33—H33119.4
C16—C15—H15B108.4C35—C34—C33117.32 (13)
C14—C15—H15B108.4C35—C34—C341121.14 (15)
H15A—C15—H15B107.5C33—C34—C341121.53 (16)
O16—C16—C11121.82 (11)C34—C341—H34A109.5
O16—C16—C15118.06 (11)C34—C341—H34B109.5
C11—C16—C15120.06 (11)H34A—C341—H34B109.5
C22—C21—C26117.50 (12)C34—C341—H34C109.5
C22—C21—C1126.16 (11)H34A—C341—H34C109.5
C26—C21—C1116.26 (11)H34B—C341—H34C109.5
O22—C22—C21124.36 (12)C34—C35—C36121.74 (13)
O22—C22—C23112.34 (10)C34—C35—H35119.1
C21—C22—C23123.30 (11)C36—C35—H35119.1
C22—O22—H22111.9 (11)C31—C36—C35121.02 (14)
C22—C23—C24113.63 (11)C31—C36—H36119.5
C22—C23—H23A108.8C35—C36—H36119.5
C21—C1—C11—C1289.99 (14)C1—C21—C22—C23171.99 (12)
C31—C1—C11—C12133.42 (12)O22—C22—C23—C24157.51 (11)
C21—C1—C11—C1686.20 (14)C21—C22—C23—C2421.41 (18)
C31—C1—C11—C1650.39 (15)C22—C23—C24—C27169.95 (11)
C16—C11—C12—O12169.84 (12)C22—C23—C24—C2550.94 (14)
C1—C11—C12—O126.4 (2)C22—C23—C24—C2869.32 (15)
C16—C11—C12—C138.70 (19)C27—C24—C25—C26171.44 (12)
C1—C11—C12—C13175.02 (12)C23—C24—C25—C2652.09 (15)
O12—C12—C13—C14157.29 (12)C28—C24—C25—C2668.30 (15)
C11—C12—C13—C1424.02 (19)C22—C21—C26—O26167.32 (13)
C12—C13—C14—C1550.13 (15)C1—C21—C26—O269.78 (19)
C12—C13—C14—C1871.10 (15)C22—C21—C26—C2510.20 (18)
C12—C13—C14—C17168.42 (12)C1—C21—C26—C25172.71 (11)
C13—C14—C15—C1648.07 (15)C24—C25—C26—O26158.99 (13)
C18—C14—C15—C1672.81 (16)C24—C25—C26—C2123.42 (18)
C17—C14—C15—C16166.68 (12)C21—C1—C31—C363.99 (17)
C12—C11—C16—O16165.99 (12)C11—C1—C31—C36139.89 (12)
C1—C11—C16—O1610.36 (18)C21—C1—C31—C32174.95 (11)
C12—C11—C16—C1511.34 (17)C11—C1—C31—C3249.16 (15)
C1—C11—C16—C15172.31 (11)C36—C31—C32—C330.94 (18)
C14—C15—C16—O16163.65 (11)C1—C31—C32—C33170.64 (11)
C14—C15—C16—C1118.93 (17)C31—C32—C33—C340.7 (2)
C11—C1—C21—C2281.04 (15)C32—C33—C34—C350.3 (2)
C31—C1—C21—C2254.17 (17)C32—C33—C34—C341179.32 (13)
C11—C1—C21—C2695.76 (13)C33—C34—C35—C361.0 (2)
C31—C1—C21—C26129.03 (12)C341—C34—C35—C36178.62 (13)
C26—C21—C22—O22169.98 (11)C32—C31—C36—C350.24 (18)
C1—C21—C22—O226.8 (2)C1—C31—C36—C35170.77 (12)
C26—C21—C22—C2311.24 (18)C34—C35—C36—C310.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12—H12···O260.98 (2)1.73 (2)2.6946 (16)168 (2)
O22—H22···O160.99 (2)1.60 (2)2.5714 (13)168.0 (18)
(V) ; top
Crystal data top
C24H30O5F(000) = 856
Mr = 398.48Dx = 1.228 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.916 (2) ÅCell parameters from 5837 reflections
b = 11.573 (2) Åθ = 0–25°
c = 21.106 (5) ŵ = 0.09 mm1
β = 98.15 (1)°T = 173 K
V = 2155.8 (8) Å3Block, colourless
Z = 40.70 × 0.40 × 0.30 mm
Data collection top
Siemens CCD three-circle
diffractometer
4937 independent reflections
Radiation source: fine-focus sealed tube3429 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: empirical
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.943, Tmax = 0.975k = 1515
40510 measured reflectionsl = 2727
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H 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 reflectionsΔρmax = 0.28 e Å3
271 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
C10.82530 (18)0.51194 (14)0.73424 (7)0.0263 (4)
H10.87700.58290.75350.032*
C110.76832 (19)0.45263 (14)0.79124 (7)0.0274 (4)
C120.8310 (2)0.47770 (15)0.85297 (8)0.0349 (4)
O120.95248 (17)0.54521 (12)0.86878 (7)0.0467 (4)
H121.007 (3)0.560 (2)0.8347 (13)0.087 (9)*
C130.7711 (2)0.42951 (17)0.91050 (8)0.0428 (5)
H13A0.77970.48950.94430.051*
H13B0.83540.36350.92720.051*
C140.6058 (2)0.38888 (16)0.89720 (8)0.0391 (5)
C170.5677 (3)0.31637 (19)0.95391 (9)0.0533 (6)
H17A0.57850.36420.99260.080*
H17B0.63720.25050.96070.080*
H17C0.46330.28820.94460.080*
C180.4976 (3)0.49287 (19)0.88693 (11)0.0590 (7)
H18A0.50970.54090.92560.089*
H18B0.39280.46520.87810.089*
H18C0.52140.53870.85060.089*
C150.5886 (2)0.31344 (15)0.83700 (8)0.0334 (4)
H15A0.63810.23810.84810.040*
H15B0.47940.29840.82360.040*
C160.65382 (18)0.36374 (14)0.78094 (8)0.0268 (4)
O160.60897 (13)0.32244 (10)0.72668 (5)0.0307 (3)
C210.95100 (18)0.44752 (14)0.70696 (7)0.0260 (3)
C220.93272 (18)0.35419 (14)0.66663 (7)0.0250 (3)
O220.80136 (13)0.29910 (10)0.64860 (6)0.0285 (3)
H220.730 (3)0.319 (2)0.6760 (12)0.071 (8)*
C231.06029 (18)0.30249 (14)0.63670 (8)0.0295 (4)
H23A1.02040.27560.59300.035*
H23B1.09960.23420.66200.035*
C241.19148 (19)0.38673 (15)0.63261 (8)0.0303 (4)
C271.3256 (2)0.32132 (18)0.61188 (9)0.0406 (5)
H27A1.40920.37520.60920.061*
H27B1.29450.28590.56990.061*
H27C1.35890.26090.64330.061*
C281.1410 (2)0.48334 (17)0.58372 (9)0.0418 (5)
H28A1.05490.52510.59690.063*
H28B1.11090.44910.54130.063*
H28C1.22520.53710.58190.063*
C251.23590 (19)0.43671 (16)0.70022 (8)0.0337 (4)
H25A1.28520.37510.72830.040*
H25B1.31140.49880.69820.040*
C261.1054 (2)0.48496 (15)0.73009 (8)0.0314 (4)
O261.13391 (14)0.55430 (12)0.77591 (6)0.0443 (3)
C310.69506 (18)0.56040 (13)0.68500 (7)0.0251 (3)
C320.58910 (19)0.63297 (14)0.70822 (8)0.0273 (4)
H320.59170.64110.75310.033*
C330.48054 (19)0.69318 (14)0.66740 (8)0.0299 (4)
H330.41090.74210.68470.036*
C340.47303 (19)0.68223 (14)0.60104 (8)0.0282 (4)
O3410.36203 (14)0.74640 (11)0.56478 (6)0.0368 (3)
C3410.3500 (2)0.73812 (19)0.49658 (9)0.0447 (5)
H34A0.26720.78770.47680.067*
H34B0.32910.65790.48340.067*
H34C0.44530.76310.48280.067*
C350.57546 (19)0.61018 (14)0.57668 (8)0.0286 (4)
H350.57100.60080.53170.034*
C360.68599 (19)0.55096 (14)0.61880 (8)0.0272 (4)
H360.75660.50300.60150.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0309 (9)0.0224 (8)0.0250 (8)0.0019 (7)0.0024 (7)0.0026 (6)
C110.0345 (9)0.0246 (8)0.0231 (8)0.0058 (7)0.0047 (7)0.0004 (6)
C120.0471 (11)0.0282 (9)0.0284 (9)0.0067 (8)0.0014 (8)0.0043 (7)
O120.0563 (9)0.0486 (8)0.0322 (7)0.0070 (7)0.0037 (7)0.0103 (6)
C130.0690 (14)0.0378 (10)0.0216 (9)0.0094 (10)0.0058 (9)0.0019 (8)
C140.0597 (13)0.0323 (10)0.0288 (9)0.0165 (9)0.0181 (9)0.0055 (8)
C170.0814 (16)0.0501 (12)0.0336 (11)0.0156 (12)0.0259 (11)0.0075 (9)
C180.0848 (17)0.0476 (12)0.0513 (13)0.0334 (12)0.0326 (12)0.0076 (10)
C150.0418 (10)0.0296 (9)0.0312 (9)0.0076 (8)0.0131 (8)0.0055 (7)
C160.0292 (9)0.0263 (8)0.0256 (8)0.0091 (7)0.0061 (7)0.0029 (7)
O160.0312 (6)0.0346 (6)0.0268 (6)0.0036 (5)0.0062 (5)0.0001 (5)
C210.0281 (8)0.0243 (8)0.0251 (8)0.0014 (7)0.0019 (6)0.0010 (6)
C220.0260 (8)0.0247 (8)0.0240 (8)0.0031 (7)0.0025 (6)0.0028 (6)
O220.0270 (6)0.0294 (6)0.0298 (6)0.0066 (5)0.0064 (5)0.0035 (5)
C230.0297 (9)0.0284 (9)0.0312 (9)0.0015 (7)0.0066 (7)0.0021 (7)
C240.0254 (8)0.0346 (9)0.0308 (9)0.0032 (7)0.0034 (7)0.0020 (7)
C270.0292 (9)0.0556 (12)0.0377 (10)0.0004 (9)0.0072 (8)0.0022 (9)
C280.0384 (11)0.0459 (11)0.0411 (11)0.0062 (9)0.0054 (8)0.0123 (9)
C250.0260 (9)0.0370 (10)0.0370 (10)0.0045 (8)0.0005 (7)0.0004 (8)
C260.0327 (9)0.0277 (9)0.0320 (9)0.0030 (7)0.0015 (7)0.0001 (7)
O260.0375 (7)0.0454 (8)0.0473 (8)0.0051 (6)0.0029 (6)0.0175 (6)
C310.0284 (8)0.0200 (8)0.0265 (8)0.0049 (6)0.0029 (6)0.0014 (6)
C320.0336 (9)0.0246 (8)0.0238 (8)0.0036 (7)0.0052 (7)0.0012 (6)
C330.0328 (9)0.0260 (8)0.0316 (9)0.0001 (7)0.0067 (7)0.0021 (7)
C340.0286 (9)0.0244 (8)0.0304 (9)0.0029 (7)0.0002 (7)0.0041 (7)
O3410.0391 (7)0.0380 (7)0.0320 (7)0.0081 (6)0.0005 (5)0.0040 (5)
C3410.0501 (12)0.0508 (12)0.0310 (10)0.0101 (10)0.0016 (9)0.0081 (9)
C350.0345 (9)0.0275 (8)0.0236 (8)0.0040 (7)0.0035 (7)0.0002 (7)
C360.0314 (9)0.0234 (8)0.0272 (8)0.0012 (7)0.0054 (7)0.0010 (7)
Geometric parameters (Å, º) top
C1—C211.525 (2)C23—H23A0.9900
C1—C111.533 (2)C23—H23B0.9900
C1—C311.549 (2)C24—C271.530 (2)
C1—H11.0000C24—C251.539 (2)
C11—C121.374 (2)C24—C281.545 (2)
C11—C161.444 (2)C27—H27A0.9800
C12—O121.339 (2)C27—H27B0.9800
C12—C131.502 (3)C27—H27C0.9800
O12—H120.94 (3)C28—H28A0.9800
C13—C141.535 (3)C28—H28B0.9800
C13—H13A0.9900C28—H28C0.9800
C13—H13B0.9900C25—C261.507 (2)
C14—C151.531 (2)C25—H25A0.9900
C14—C181.538 (3)C25—H25B0.9900
C14—C171.539 (3)C26—O261.255 (2)
C17—H17A0.9800C31—C361.392 (2)
C17—H17B0.9800C31—C321.403 (2)
C17—H17C0.9800C32—C331.389 (2)
C18—H18A0.9800C32—H320.9500
C18—H18B0.9800C33—C341.398 (2)
C18—H18C0.9800C33—H330.9500
C15—C161.507 (2)C34—O3411.379 (2)
C15—H15A0.9900C34—C351.388 (2)
C15—H15B0.9900O341—C3411.431 (2)
C16—O161.2531 (19)C341—H34A0.9800
C21—C221.371 (2)C341—H34B0.9800
C21—C261.460 (2)C341—H34C0.9800
C22—O221.3404 (19)C35—C361.408 (2)
C22—C231.501 (2)C35—H350.9500
O22—H220.94 (3)C36—H360.9500
C23—C241.534 (2)
C21—C1—C11114.86 (13)C22—C23—H23B108.9
C21—C1—C31116.40 (13)C24—C23—H23B108.9
C11—C1—C31112.84 (13)H23A—C23—H23B107.7
C21—C1—H1103.5C27—C24—C23109.54 (15)
C11—C1—H1103.5C27—C24—C25110.01 (14)
C31—C1—H1103.5C23—C24—C25106.54 (13)
C12—C11—C16118.50 (15)C27—C24—C28109.42 (15)
C12—C11—C1120.93 (16)C23—C24—C28110.19 (14)
C16—C11—C1120.46 (14)C25—C24—C28111.09 (15)
O12—C12—C11124.45 (17)C24—C27—H27A109.5
O12—C12—C13112.54 (16)C24—C27—H27B109.5
C11—C12—C13123.00 (17)H27A—C27—H27B109.5
C12—O12—H12113.9 (17)C24—C27—H27C109.5
C12—C13—C14114.11 (15)H27A—C27—H27C109.5
C12—C13—H13A108.7H27B—C27—H27C109.5
C14—C13—H13A108.7C24—C28—H28A109.5
C12—C13—H13B108.7C24—C28—H28B109.5
C14—C13—H13B108.7H28A—C28—H28B109.5
H13A—C13—H13B107.6C24—C28—H28C109.5
C15—C14—C13107.90 (15)H28A—C28—H28C109.5
C15—C14—C18109.99 (16)H28B—C28—H28C109.5
C13—C14—C18110.66 (17)C26—C25—C24114.51 (14)
C15—C14—C17109.10 (16)C26—C25—H25A108.6
C13—C14—C17109.69 (17)C24—C25—H25A108.6
C18—C14—C17109.46 (16)C26—C25—H25B108.6
C14—C17—H17A109.5C24—C25—H25B108.6
C14—C17—H17B109.5H25A—C25—H25B107.6
H17A—C17—H17B109.5O26—C26—C21121.71 (16)
C14—C17—H17C109.5O26—C26—C25118.41 (15)
H17A—C17—H17C109.5C21—C26—C25119.84 (15)
H17B—C17—H17C109.5C36—C31—C32116.82 (15)
C14—C18—H18A109.5C36—C31—C1125.18 (15)
C14—C18—H18B109.5C32—C31—C1117.39 (14)
H18A—C18—H18B109.5C33—C32—C31121.89 (15)
C14—C18—H18C109.5C33—C32—H32119.1
H18A—C18—H18C109.5C31—C32—H32119.1
H18B—C18—H18C109.5C32—C33—C34120.41 (15)
C16—C15—C14115.25 (15)C32—C33—H33119.8
C16—C15—H15A108.5C34—C33—H33119.8
C14—C15—H15A108.5O341—C34—C35125.17 (15)
C16—C15—H15B108.5O341—C34—C33115.84 (15)
C14—C15—H15B108.5C35—C34—C33118.99 (15)
H15A—C15—H15B107.5C34—O341—C341117.90 (14)
O16—C16—C11122.44 (15)O341—C341—H34A109.5
O16—C16—C15117.48 (15)O341—C341—H34B109.5
C11—C16—C15120.03 (15)H34A—C341—H34B109.5
C22—C21—C26117.71 (15)O341—C341—H34C109.5
C22—C21—C1126.21 (15)H34A—C341—H34C109.5
C26—C21—C1115.94 (14)H34B—C341—H34C109.5
O22—C22—C21124.98 (15)C34—C35—C36119.80 (15)
O22—C22—C23112.00 (14)C34—C35—H35120.1
C21—C22—C23123.02 (15)C36—C35—H35120.1
C22—O22—H22110.2 (15)C31—C36—C35122.09 (15)
C22—C23—C24113.54 (14)C31—C36—H36119.0
C22—C23—H23A108.9C35—C36—H36119.0
C24—C23—H23A108.9
C21—C1—C11—C1291.70 (19)O22—C22—C23—C24156.41 (13)
C31—C1—C11—C12131.68 (16)C21—C22—C23—C2423.0 (2)
C21—C1—C11—C1684.39 (19)C22—C23—C24—C27170.80 (14)
C31—C1—C11—C1652.24 (19)C22—C23—C24—C2551.84 (18)
C16—C11—C12—O12169.76 (16)C22—C23—C24—C2868.77 (19)
C1—C11—C12—O126.4 (3)C27—C24—C25—C26169.90 (15)
C16—C11—C12—C139.0 (3)C23—C24—C25—C2651.24 (19)
C1—C11—C12—C13174.83 (15)C28—C24—C25—C2668.79 (19)
O12—C12—C13—C14159.54 (15)C22—C21—C26—O26166.27 (16)
C11—C12—C13—C1421.6 (2)C1—C21—C26—O269.6 (2)
C12—C13—C14—C1548.2 (2)C22—C21—C26—C2511.5 (2)
C12—C13—C14—C1872.2 (2)C1—C21—C26—C25172.65 (15)
C12—C13—C14—C17166.90 (15)C24—C25—C26—O26160.70 (16)
C13—C14—C15—C1648.22 (19)C24—C25—C26—C2121.4 (2)
C18—C14—C15—C1672.6 (2)C21—C1—C31—C361.0 (2)
C17—C14—C15—C16167.34 (16)C11—C1—C31—C36136.92 (16)
C12—C11—C16—O16168.02 (15)C21—C1—C31—C32171.66 (14)
C1—C11—C16—O168.2 (2)C11—C1—C31—C3252.42 (19)
C12—C11—C16—C159.3 (2)C36—C31—C32—C330.3 (2)
C1—C11—C16—C15174.56 (14)C1—C31—C32—C33171.15 (15)
C14—C15—C16—O16161.40 (15)C31—C32—C33—C340.5 (2)
C14—C15—C16—C1121.2 (2)C32—C33—C34—O341179.47 (14)
C11—C1—C21—C2279.2 (2)C32—C33—C34—C350.1 (2)
C31—C1—C21—C2255.8 (2)C35—C34—O341—C3410.4 (2)
C11—C1—C21—C2696.23 (17)C33—C34—O341—C341179.95 (16)
C31—C1—C21—C26128.73 (15)O341—C34—C35—C36178.62 (15)
C26—C21—C22—O22169.95 (15)C33—C34—C35—C360.9 (2)
C1—C21—C22—O225.4 (3)C32—C31—C36—C350.5 (2)
C26—C21—C22—C2310.8 (2)C1—C31—C36—C35171.24 (15)
C1—C21—C22—C23173.87 (15)C34—C35—C36—C311.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12—H12···O260.94 (3)1.79 (3)2.714 (2)166 (3)
O22—H22···O160.94 (3)1.63 (3)2.5558 (17)167 (2)
(VI) ; top
Crystal data top
C25H33NO4F(000) = 888
Mr = 411.52Dx = 1.218 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 9.223 (1) ÅCell parameters from 8192 reflections
b = 12.012 (1) Åθ = 0–25°
c = 20.661 (1) ŵ = 0.08 mm1
β = 101.42 (1)°T = 173 K
V = 2243.6 (3) Å3Block, colourless
Z = 40.35 × 0.25 × 0.20 mm
Data collection top
Siemens CCD three-circle
diffractometer
4957 independent reflections
Radiation source: fine-focus sealed tube3598 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
ω scansθmax = 27.1°, θmin = 2.0°
Absorption correction: empirical
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.972, Tmax = 0.984k = 1515
35071 measured reflectionsl = 2626
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H 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 reflectionsΔρmax = 0.35 e Å3
282 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
C10.8657 (2)0.53018 (17)0.74095 (9)0.0231 (4)
H10.91600.60050.75900.028*
C110.8191 (2)0.47659 (16)0.80095 (9)0.0231 (4)
C120.8884 (2)0.50323 (17)0.86411 (10)0.0261 (4)
O121.00785 (16)0.56829 (13)0.87822 (7)0.0355 (4)
H121.061 (4)0.579 (3)0.8393 (17)0.099 (12)*
C130.8402 (2)0.46069 (19)0.92446 (10)0.0310 (5)
H13A0.85600.51980.95850.037*
H13B0.90330.39660.94210.037*
C140.6771 (2)0.42407 (18)0.91232 (10)0.0284 (5)
C170.5740 (2)0.5256 (2)0.90163 (11)0.0376 (5)
H17A0.59370.57290.94100.056*
H17B0.47080.50050.89360.056*
H17C0.59150.56810.86340.056*
C180.6518 (3)0.3580 (2)0.97282 (10)0.0401 (6)
H18A0.66960.40641.01180.060*
H18B0.72000.29460.98030.060*
H18C0.54960.33080.96500.060*
C150.6493 (2)0.34879 (17)0.85144 (9)0.0267 (4)
H15A0.69690.27590.86380.032*
H15B0.54150.33570.83830.032*
C160.7044 (2)0.39282 (17)0.79255 (9)0.0234 (4)
O160.65153 (15)0.35120 (12)0.73719 (6)0.0287 (3)
C210.9861 (2)0.46661 (16)0.71509 (9)0.0240 (4)
C220.9634 (2)0.37295 (17)0.67564 (9)0.0235 (4)
O220.83501 (15)0.32114 (12)0.65923 (7)0.0276 (3)
H220.760 (4)0.346 (3)0.6886 (16)0.083 (10)*
C231.0843 (2)0.31913 (17)0.64714 (10)0.0273 (4)
H23A1.04150.29020.60260.033*
H23B1.12430.25500.67520.033*
C241.2118 (2)0.39863 (18)0.64194 (10)0.0284 (5)
C271.3422 (2)0.3344 (2)0.62404 (11)0.0388 (6)
H27A1.31090.29930.58070.058*
H27B1.37510.27690.65740.058*
H27C1.42380.38590.62260.058*
C281.1606 (3)0.4871 (2)0.58831 (11)0.0406 (6)
H28A1.12980.45050.54540.061*
H28B1.24230.53840.58640.061*
H28C1.07710.52880.59900.061*
C251.2610 (2)0.45332 (19)0.70986 (10)0.0328 (5)
H25A1.31230.39680.74110.039*
H25B1.33330.51270.70620.039*
C261.1367 (2)0.50313 (18)0.73830 (10)0.0276 (4)
O261.17034 (16)0.57352 (14)0.78376 (8)0.0390 (4)
C310.7331 (2)0.57102 (16)0.68954 (9)0.0235 (4)
C320.6268 (2)0.63590 (17)0.71198 (10)0.0261 (4)
H320.63370.64400.75820.031*
C330.5124 (2)0.68855 (17)0.66985 (10)0.0279 (4)
H330.44350.73210.68750.034*
C340.4967 (2)0.67821 (17)0.60064 (10)0.0275 (4)
N340.3856 (2)0.73441 (17)0.55816 (9)0.0375 (5)
C3410.2822 (3)0.8036 (2)0.58426 (12)0.0428 (6)
H34D0.21880.84360.54800.064*
H34E0.33690.85740.61560.064*
H34F0.22080.75680.60690.064*
C3420.3579 (3)0.7116 (2)0.48829 (11)0.0468 (6)
H34A0.26710.74950.46670.070*
H34B0.34650.63110.48100.070*
H34C0.44120.73850.46970.070*
C350.6014 (2)0.61094 (17)0.57772 (10)0.0281 (4)
H350.59290.60020.53160.034*
C360.7164 (2)0.56017 (17)0.62113 (9)0.0262 (4)
H360.78580.51670.60380.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0225 (9)0.0233 (10)0.0231 (9)0.0021 (8)0.0038 (7)0.0009 (8)
C110.0214 (9)0.0245 (10)0.0233 (9)0.0037 (8)0.0041 (7)0.0022 (8)
C120.0231 (10)0.0268 (11)0.0274 (10)0.0036 (8)0.0029 (8)0.0025 (8)
O120.0309 (8)0.0436 (9)0.0307 (8)0.0093 (7)0.0027 (6)0.0081 (7)
C130.0286 (11)0.0396 (12)0.0237 (10)0.0039 (9)0.0024 (8)0.0016 (9)
C140.0251 (10)0.0366 (12)0.0242 (10)0.0058 (9)0.0063 (8)0.0008 (9)
C170.0335 (12)0.0441 (14)0.0370 (12)0.0099 (10)0.0112 (10)0.0030 (10)
C180.0386 (13)0.0571 (16)0.0268 (11)0.0040 (11)0.0119 (9)0.0052 (11)
C150.0240 (10)0.0298 (11)0.0271 (10)0.0019 (9)0.0066 (8)0.0027 (8)
C160.0198 (9)0.0280 (10)0.0216 (9)0.0054 (8)0.0022 (7)0.0019 (8)
O160.0255 (7)0.0354 (8)0.0243 (7)0.0032 (6)0.0025 (6)0.0014 (6)
C210.0246 (10)0.0246 (10)0.0225 (9)0.0003 (8)0.0044 (8)0.0009 (8)
C220.0238 (10)0.0257 (10)0.0203 (9)0.0008 (8)0.0029 (7)0.0042 (8)
O220.0252 (7)0.0315 (8)0.0255 (7)0.0057 (6)0.0037 (6)0.0019 (6)
C230.0280 (10)0.0260 (10)0.0275 (10)0.0002 (9)0.0050 (8)0.0031 (8)
C240.0234 (10)0.0350 (12)0.0271 (10)0.0004 (9)0.0059 (8)0.0035 (9)
C270.0287 (11)0.0516 (15)0.0372 (12)0.0019 (10)0.0093 (9)0.0129 (11)
C280.0378 (13)0.0475 (14)0.0378 (12)0.0048 (11)0.0107 (10)0.0071 (11)
C250.0246 (10)0.0408 (13)0.0326 (11)0.0034 (9)0.0048 (8)0.0076 (10)
C260.0257 (10)0.0302 (11)0.0266 (10)0.0025 (9)0.0044 (8)0.0024 (9)
O260.0302 (8)0.0459 (10)0.0409 (9)0.0107 (7)0.0072 (7)0.0194 (8)
C310.0250 (10)0.0205 (9)0.0250 (10)0.0020 (8)0.0049 (8)0.0019 (8)
C320.0288 (10)0.0252 (10)0.0256 (10)0.0001 (8)0.0083 (8)0.0007 (8)
C330.0259 (10)0.0284 (11)0.0308 (11)0.0014 (9)0.0085 (8)0.0005 (9)
C340.0245 (10)0.0277 (11)0.0296 (10)0.0021 (8)0.0033 (8)0.0030 (9)
N340.0312 (10)0.0479 (12)0.0308 (10)0.0097 (9)0.0000 (8)0.0023 (9)
C3410.0323 (12)0.0486 (15)0.0446 (14)0.0117 (11)0.0007 (10)0.0053 (11)
C3420.0538 (15)0.0460 (15)0.0330 (13)0.0093 (12)0.0094 (11)0.0002 (11)
C350.0337 (11)0.0287 (11)0.0214 (9)0.0037 (9)0.0044 (8)0.0014 (8)
C360.0279 (10)0.0250 (10)0.0264 (10)0.0020 (8)0.0069 (8)0.0019 (8)
Geometric parameters (Å, º) top
C1—C211.529 (3)C24—C271.534 (3)
C1—C111.532 (3)C24—C251.534 (3)
C1—C311.532 (3)C24—C281.541 (3)
C1—H11.0000C27—H27A0.9800
C11—C121.373 (3)C27—H27B0.9800
C11—C161.445 (3)C27—H27C0.9800
C12—O121.335 (2)C28—H28A0.9800
C12—C131.494 (3)C28—H28B0.9800
O12—H121.03 (4)C28—H28C0.9800
C13—C141.540 (3)C25—C261.511 (3)
C13—H13A0.9900C25—H25A0.9900
C13—H13B0.9900C25—H25B0.9900
C14—C151.529 (3)C26—O261.256 (2)
C14—C171.536 (3)C31—C361.397 (3)
C14—C181.537 (3)C31—C321.402 (3)
C17—H17A0.9800C32—C331.381 (3)
C17—H17B0.9800C32—H320.9500
C17—H17C0.9800C33—C341.414 (3)
C18—H18A0.9800C33—H330.9500
C18—H18B0.9800C34—N341.386 (3)
C18—H18C0.9800C34—C351.411 (3)
C15—C161.505 (3)N34—C3421.442 (3)
C15—H15A0.9900N34—C3411.448 (3)
C15—H15B0.9900C341—H34D0.9800
C16—O161.255 (2)C341—H34E0.9800
C21—C221.381 (3)C341—H34F0.9800
C21—C261.445 (3)C342—H34A0.9800
C22—O221.321 (2)C342—H34B0.9800
C22—C231.507 (3)C342—H34C0.9800
O22—H221.05 (3)C35—C361.387 (3)
C23—C241.535 (3)C35—H350.9500
C23—H23A0.9900C36—H360.9500
C23—H23B0.9900
C21—C1—C11114.36 (16)C27—C24—C23110.59 (18)
C21—C1—C31116.91 (16)C25—C24—C23107.11 (16)
C11—C1—C31112.49 (15)C27—C24—C28108.48 (18)
C21—C1—H1103.7C25—C24—C28110.81 (19)
C11—C1—H1103.7C23—C24—C28110.46 (17)
C31—C1—H1103.7C24—C27—H27A109.5
C12—C11—C16117.96 (17)C24—C27—H27B109.5
C12—C11—C1121.25 (18)H27A—C27—H27B109.5
C16—C11—C1120.74 (16)C24—C27—H27C109.5
O12—C12—C11123.59 (19)H27A—C27—H27C109.5
O12—C12—C13112.76 (17)H27B—C27—H27C109.5
C11—C12—C13123.63 (19)C24—C28—H28A109.5
C12—O12—H12114 (2)C24—C28—H28B109.5
C12—C13—C14113.85 (16)H28A—C28—H28B109.5
C12—C13—H13A108.8C24—C28—H28C109.5
C14—C13—H13A108.8H28A—C28—H28C109.5
C12—C13—H13B108.8H28B—C28—H28C109.5
C14—C13—H13B108.8C26—C25—C24114.56 (17)
H13A—C13—H13B107.7C26—C25—H25A108.6
C15—C14—C17110.66 (17)C24—C25—H25A108.6
C15—C14—C18109.60 (18)C26—C25—H25B108.6
C17—C14—C18109.74 (18)C24—C25—H25B108.6
C15—C14—C13107.62 (16)H25A—C25—H25B107.6
C17—C14—C13110.75 (19)O26—C26—C21122.08 (18)
C18—C14—C13108.42 (17)O26—C26—C25117.62 (18)
C14—C17—H17A109.5C21—C26—C25120.26 (18)
C14—C17—H17B109.5C36—C31—C32116.22 (18)
H17A—C17—H17B109.5C36—C31—C1125.78 (17)
C14—C17—H17C109.5C32—C31—C1117.58 (17)
H17A—C17—H17C109.5C33—C32—C31122.93 (18)
H17B—C17—H17C109.5C33—C32—H32118.5
C14—C18—H18A109.5C31—C32—H32118.5
C14—C18—H18B109.5C32—C33—C34120.64 (19)
H18A—C18—H18B109.5C32—C33—H33119.7
C14—C18—H18C109.5C34—C33—H33119.7
H18A—C18—H18C109.5N34—C34—C35122.40 (18)
H18B—C18—H18C109.5N34—C34—C33120.83 (19)
C16—C15—C14115.38 (17)C35—C34—C33116.75 (18)
C16—C15—H15A108.4C34—N34—C342120.25 (19)
C14—C15—H15A108.4C34—N34—C341120.20 (18)
C16—C15—H15B108.4C342—N34—C341118.89 (19)
C14—C15—H15B108.4N34—C341—H34D109.5
H15A—C15—H15B107.5N34—C341—H34E109.5
O16—C16—C11122.01 (17)H34D—C341—H34E109.5
O16—C16—C15117.66 (18)N34—C341—H34F109.5
C11—C16—C15120.28 (17)H34D—C341—H34F109.5
C22—C21—C26117.84 (18)H34E—C341—H34F109.5
C22—C21—C1125.25 (17)N34—C342—H34A109.5
C26—C21—C1116.72 (17)N34—C342—H34B109.5
O22—C22—C21124.01 (18)H34A—C342—H34B109.5
O22—C22—C23113.13 (17)N34—C342—H34C109.5
C21—C22—C23122.86 (17)H34A—C342—H34C109.5
C22—O22—H22112.2 (18)H34B—C342—H34C109.5
C22—C23—C24113.40 (17)C36—C35—C34121.41 (18)
C22—C23—H23A108.9C36—C35—H35119.3
C24—C23—H23A108.9C34—C35—H35119.3
C22—C23—H23B108.9C35—C36—C31122.03 (19)
C24—C23—H23B108.9C35—C36—H36119.0
H23A—C23—H23B107.7C31—C36—H36119.0
C27—C24—C25109.39 (17)
C21—C1—C11—C1290.0 (2)C21—C22—C23—C2422.9 (3)
C31—C1—C11—C12133.48 (19)C22—C23—C24—C27170.25 (17)
C21—C1—C11—C1687.4 (2)C22—C23—C24—C2551.1 (2)
C31—C1—C11—C1649.1 (2)C22—C23—C24—C2869.6 (2)
C16—C11—C12—O12171.19 (18)C27—C24—C25—C26170.35 (19)
C1—C11—C12—O126.3 (3)C23—C24—C25—C2650.5 (2)
C16—C11—C12—C137.5 (3)C28—C24—C25—C2670.1 (2)
C1—C11—C12—C13174.96 (18)C22—C21—C26—O26166.32 (19)
O12—C12—C13—C14158.35 (18)C1—C21—C26—O269.0 (3)
C11—C12—C13—C1422.8 (3)C22—C21—C26—C2511.2 (3)
C12—C13—C14—C1548.5 (2)C1—C21—C26—C25173.50 (18)
C12—C13—C14—C1772.5 (2)C24—C25—C26—O26161.41 (19)
C12—C13—C14—C18167.00 (18)C24—C25—C26—C2121.0 (3)
C17—C14—C15—C1673.0 (2)C21—C1—C31—C363.4 (3)
C18—C14—C15—C16165.87 (17)C11—C1—C31—C36138.7 (2)
C13—C14—C15—C1648.2 (2)C21—C1—C31—C32175.76 (17)
C12—C11—C16—O16168.79 (18)C11—C1—C31—C3248.9 (2)
C1—C11—C16—O168.7 (3)C36—C31—C32—C331.1 (3)
C12—C11—C16—C158.4 (3)C1—C31—C32—C33171.98 (19)
C1—C11—C16—C15174.05 (17)C31—C32—C33—C340.5 (3)
C14—C15—C16—O16161.30 (17)C32—C33—C34—N34177.4 (2)
C14—C15—C16—C1121.4 (3)C32—C33—C34—C350.9 (3)
C11—C1—C21—C2279.4 (2)C35—C34—N34—C34210.3 (3)
C31—C1—C21—C2255.1 (3)C33—C34—N34—C342171.5 (2)
C11—C1—C21—C2695.5 (2)C35—C34—N34—C341179.1 (2)
C31—C1—C21—C26129.97 (19)C33—C34—N34—C3410.9 (3)
C26—C21—C22—O22169.51 (18)N34—C34—C35—C36176.5 (2)
C1—C21—C22—O225.4 (3)C33—C34—C35—C361.8 (3)
C26—C21—C22—C2310.2 (3)C34—C35—C36—C311.3 (3)
C1—C21—C22—C23174.94 (18)C32—C31—C36—C350.2 (3)
O22—C22—C23—C24157.40 (16)C1—C31—C36—C35172.23 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O12—H12···O261.03 (4)1.67 (4)2.686 (2)168 (3)
O22—H22···O161.05 (3)1.55 (3)2.5821 (19)166 (3)
 

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