Monitoring structural transformations in crystals. 8. Monitoring molecules and a reaction center during a solid-state Yang photocyclization

Structural changes taking place in a crystal during an intramolecular photochemical reaction [the Yang photocyclization of the α-methylbenzylamine salt with 1-(4-carboxybenzoyl)-1-methyladamantane] were monitored step-by-step using X-ray structure analysis. This is the first example of such a study carried out for an intramolecular photochemical reaction. During the photoreaction, both the reactant and product molecules change their orientation, but the reactant changes more rapidly after the reaction is about 80% complete. The distance between directly reacting atoms in the reactant molecule is almost constant until about 80% reaction progress and afterwards decreases. The torsion angle defined by the reactant atoms that form the cyclobutane ring also changes in the final stages of the photoreaction. These phenomena are explained in terms of the influence of many product molecules upon a small number of reacting molecules. The adamantane portion shifts more than the remaining part of the anionic reactant species during the reaction, which is explained in terms of hydrogen bonding. The structural changes are accompanied by changes in the cell constants. The results obtained in the present study are compared with analogous results published for intermolecular reactions.

Computing details

For all compounds, data collection: KM4CCD (Kuma Diffraction, 2000); cell refinement: KM4CCD (Kuma Diffraction, 2000); data reduction: KM4CCD (Kuma Diffraction, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

(4.4P)

Crystal data

C27H33NO3	Dx = 1.215 Mg m^−3
Mr = 419.54	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 2655 reflections
a = 11.7570 (11) Å	θ = 6–21°
b = 29.752 (2) Å	µ = 0.08 mm^−1
c = 6.5547 (5) Å	T = 293 K
V = 2292.8 (3) Å^3	Block, colourless
Z = 4	0.56 × 0.41 × 0.20 mm
F(000) = 904

Data collection

Kuma KM4CCD diffractometer	3349 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.051
Graphite monochromator	θmax = 25.0°, θmin = 6.0°
ω scans	h = −12→13
10720 measured reflections	k = −35→35
3969 independent reflections	l = −7→6

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.064	w = 1/[σ^2(Fo^2) + (0.041P)^2 + 1.2135P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.138	(Δ/σ)max = 0.001
S = 1.08	Δρmax = 0.19 e Å^−3
3969 reflections	Δρmin = −0.17 e Å^−3
406 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
342 restraints	Extinction coefficient: 0.032 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: The absolute configuration was assigned to agree with that from Leibovitch M. et all, 1997; 1998
Secondary atom site location: inferred from neighbouring sites

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1R	0.4156 (4)	0.20936 (10)	0.4836 (5)	0.0839 (11)	0.956 (5)
C1R	0.4124 (4)	0.30122 (13)	0.5260 (6)	0.0661 (12)	0.956 (5)
H1R	0.3634	0.2884	0.4200	0.079*	0.956 (5)
C2R	0.5327 (4)	0.30361 (14)	0.4470 (5)	0.0855 (15)	0.956 (5)
H2AR	0.5350	0.3216	0.3235	0.103*	0.956 (5)
H2BR	0.5596	0.2736	0.4143	0.103*	0.956 (5)
C3R	0.6087 (4)	0.32454 (15)	0.6081 (7)	0.0896 (15)	0.956 (5)
H3R	0.6868	0.3266	0.5569	0.107*	0.956 (5)
C4R	0.6055 (3)	0.29529 (14)	0.7978 (8)	0.0742 (13)	0.956 (5)
H4AR	0.6347	0.2656	0.7659	0.089*	0.956 (5)
H4BR	0.6536	0.3083	0.9026	0.089*	0.956 (5)
C5R	0.4860 (4)	0.29153 (11)	0.8752 (5)	0.0525 (9)	0.956 (5)
H5R	0.4853	0.2729	0.9985	0.063*	0.956 (5)
C6R	0.4440 (5)	0.33871 (13)	0.9286 (6)	0.0776 (14)	0.956 (5)
H6AR	0.3675	0.3370	0.9834	0.093*	0.956 (5)
H6BR	0.4929	0.3517	1.0321	0.093*	0.956 (5)
C7R	0.4445 (4)	0.36842 (11)	0.7394 (7)	0.0695 (12)	0.956 (5)
H7R	0.4160	0.3984	0.7744	0.083*	0.956 (5)
C8R	0.5641 (4)	0.37195 (14)	0.6626 (9)	0.0946 (16)	0.956 (5)
H8AR	0.6121	0.3853	0.7667	0.114*	0.956 (5)
H8BR	0.5664	0.3911	0.5429	0.114*	0.956 (5)
C9R	0.3712 (4)	0.34811 (12)	0.5769 (7)	0.0753 (14)	0.956 (5)
H9AR	0.3737	0.3667	0.4555	0.090*	0.956 (5)
H9BR	0.2931	0.3468	0.6238	0.090*	0.956 (5)
C10R	0.4093 (3)	0.27033 (10)	0.7158 (5)	0.0469 (8)	0.956 (5)
C11R	0.4422 (3)	0.22277 (11)	0.6535 (5)	0.0511 (9)	0.956 (5)
C12R	0.5032 (3)	0.18959 (10)	0.7881 (5)	0.0457 (8)	0.956 (5)
C13R	0.5843 (3)	0.16323 (12)	0.6947 (5)	0.0473 (9)	0.956 (5)
H13R	0.6041	0.1689	0.5597	0.057*	0.956 (5)
C14R	0.6363 (3)	0.12879 (11)	0.7973 (5)	0.0454 (9)	0.956 (5)
H14R	0.6917	0.1117	0.7322	0.054*	0.956 (5)
C15R	0.6069 (3)	0.11923 (10)	0.9976 (5)	0.0365 (8)	0.956 (5)
C16R	0.5297 (3)	0.14692 (11)	1.0936 (5)	0.0441 (8)	0.956 (5)
H16R	0.5120	0.1419	1.2300	0.053*	0.956 (5)
C17R	0.4779 (3)	0.18199 (11)	0.9910 (5)	0.0484 (9)	0.956 (5)
H17R	0.4263	0.2004	1.0584	0.058*	0.956 (5)
C18R	0.6573 (3)	0.07966 (13)	1.1061 (5)	0.0401 (8)	0.956 (5)
C19R	0.2867 (4)	0.26441 (17)	0.7937 (11)	0.108 (2)	0.956 (5)
H19A	0.2587	0.2927	0.8434	0.161*	0.956 (5)
H19B	0.2858	0.2427	0.9022	0.161*	0.956 (5)
H19C	0.2392	0.2541	0.6842	0.161*	0.956 (5)
O2R	0.6539 (3)	0.07858 (12)	1.2952 (4)	0.0586 (9)	0.956 (5)
O3R	0.7002 (5)	0.04917 (17)	0.9953 (6)	0.0568 (13)	0.956 (5)
O1P	0.387 (6)	0.2149 (18)	0.461 (9)	0.083 (11)*	0.044 (5)
HO1P	0.4295	0.1985	0.3955	0.125*	0.044 (5)
C1P	0.405 (4)	0.2980 (14)	0.515 (7)	0.061 (11)*	0.044 (5)
H1P	0.3601	0.2852	0.4026	0.073*	0.044 (5)
C2P	0.518 (4)	0.2731 (12)	0.531 (6)	0.14 (2)*	0.044 (5)
H2P	0.5515	0.2650	0.3992	0.168*	0.044 (5)
C3P	0.598 (4)	0.2979 (16)	0.667 (8)	0.065 (17)*	0.044 (5)
H3P	0.6753	0.2868	0.6434	0.079*	0.044 (5)
C4P	0.565 (4)	0.2892 (19)	0.886 (7)	0.05 (2)*	0.044 (5)
H4AP	0.6061	0.3092	0.9769	0.057*	0.044 (5)
H4BP	0.5815	0.2584	0.9239	0.057*	0.044 (5)
C5P	0.438 (4)	0.2985 (16)	0.893 (7)	0.07 (2)*	0.044 (5)
H5P	0.4069	0.2886	1.0247	0.080*	0.044 (5)
C6P	0.424 (5)	0.3502 (16)	0.873 (9)	0.049 (17)*	0.044 (5)
H6AP	0.3441	0.3581	0.8785	0.059*	0.044 (5)
H6BP	0.4623	0.3650	0.9861	0.059*	0.044 (5)
C7P	0.476 (5)	0.3662 (14)	0.670 (10)	0.09 (2)*	0.044 (5)
H7P	0.4762	0.3991	0.6660	0.104*	0.044 (5)
C8P	0.595 (4)	0.3483 (16)	0.629 (10)	0.072 (19)*	0.044 (5)
H8AP	0.6162	0.3546	0.4887	0.086*	0.044 (5)
H8BP	0.6491	0.3632	0.7177	0.086*	0.044 (5)
C9P	0.402 (5)	0.3485 (15)	0.502 (9)	0.09 (2)*	0.044 (5)
H9AP	0.4306	0.3585	0.3711	0.109*	0.044 (5)
H9BP	0.3248	0.3593	0.5183	0.109*	0.044 (5)
C10P	0.374 (3)	0.2740 (12)	0.717 (7)	0.036 (11)*	0.044 (5)
C11P	0.450 (4)	0.2356 (11)	0.629 (6)	0.09 (2)*	0.044 (5)
C12P	0.500 (3)	0.1973 (11)	0.750 (5)	0.026 (10)*	0.044 (5)
C13P	0.591 (5)	0.1738 (17)	0.674 (8)	0.042 (18)*	0.044 (5)
H13P	0.6217	0.1817	0.5481	0.050*	0.044 (5)
C14P	0.639 (5)	0.1387 (19)	0.783 (9)	0.036 (11)*	0.044 (5)
H14P	0.7012	0.1235	0.7290	0.044*	0.044 (5)
C15P	0.595 (5)	0.1258 (15)	0.971 (7)	0.038 (18)*	0.044 (5)
C16P	0.502 (5)	0.1497 (19)	1.046 (7)	0.028 (16)*	0.044 (5)
H16P	0.4709	0.1418	1.1712	0.034*	0.044 (5)
C17P	0.457 (4)	0.1847 (18)	0.937 (6)	0.045 (19)*	0.044 (5)
H17P	0.3956	0.2004	0.9909	0.054*	0.044 (5)
C18P	0.646 (6)	0.0882 (18)	1.085 (7)	0.05 (2)*	0.044 (5)
C19P	0.251 (3)	0.2661 (19)	0.762 (12)	0.09 (2)*	0.044 (5)
H19D	0.2440	0.2527	0.8945	0.131*	0.044 (5)
H19E	0.2199	0.2464	0.6610	0.131*	0.044 (5)
H19F	0.2115	0.2943	0.7598	0.131*	0.044 (5)
O2P	0.654 (6)	0.0910 (19)	1.276 (7)	0.032 (18)*	0.044 (5)
O3P	0.704 (9)	0.059 (2)	0.987 (10)	0.04 (3)*	0.044 (5)
N1R	0.6514 (2)	0.01673 (10)	0.6050 (5)	0.0448 (7)	0.956 (5)
H1NR	0.7025	−0.0012	0.5465	0.067*	0.956 (5)
H2NR	0.6731	0.0230	0.7319	0.067*	0.956 (5)
H3NR	0.6457	0.0421	0.5340	0.067*	0.956 (5)
C20R	0.5396 (3)	−0.00611 (11)	0.6093 (6)	0.0538 (10)	0.956 (5)
H20R	0.5448	−0.0308	0.7076	0.065*	0.956 (5)
C21R	0.5181 (4)	−0.02673 (15)	0.3988 (7)	0.0789 (13)	0.956 (5)
H21A	0.5825	−0.0446	0.3595	0.118*	0.956 (5)
H21B	0.5069	−0.0032	0.3007	0.118*	0.956 (5)
H21C	0.4515	−0.0454	0.4040	0.118*	0.956 (5)
C22R	0.4485 (3)	0.02501 (11)	0.6811 (6)	0.0541 (9)	0.956 (5)
C23R	0.4181 (3)	0.06281 (12)	0.5744 (8)	0.0745 (13)	0.956 (5)
H23R	0.4526	0.0689	0.4498	0.089*	0.956 (5)
C24R	0.3363 (4)	0.09211 (15)	0.6504 (10)	0.102 (2)	0.956 (5)
H24R	0.3176	0.1180	0.5786	0.122*	0.956 (5)
C25R	0.2848 (4)	0.0828 (2)	0.8274 (11)	0.113 (2)	0.956 (5)
H25R	0.2296	0.1023	0.8768	0.135*	0.956 (5)
C26R	0.3109 (4)	0.0457 (2)	0.9355 (8)	0.109 (2)	0.956 (5)
H26R	0.2735	0.0397	1.0575	0.131*	0.956 (5)
C27R	0.3937 (4)	0.01682 (17)	0.8638 (7)	0.0791 (13)	0.956 (5)
H27R	0.4128	−0.0085	0.9396	0.095*	0.956 (5)
N1P	0.640 (4)	0.000 (2)	0.619 (11)	0.042 (11)*	0.044 (5)
H1NP	0.6882	−0.0216	0.5801	0.063*	0.044 (5)
H2NP	0.6393	0.0015	0.7546	0.063*	0.044 (5)
H3NP	0.6619	0.0260	0.5673	0.063*	0.044 (5)
C20P	0.524 (4)	−0.0112 (17)	0.545 (9)	0.044 (11)*	0.044 (5)
H20P	0.4997	−0.0394	0.6077	0.053*	0.044 (5)
C21P	0.530 (8)	−0.018 (4)	0.316 (10)	0.084 (12)*	0.044 (5)
H21D	0.5947	−0.0363	0.2836	0.126*	0.044 (5)
H21E	0.5377	0.0107	0.2503	0.126*	0.044 (5)
H21F	0.4619	−0.0324	0.2701	0.126*	0.044 (5)
C22P	0.442 (3)	0.0250 (13)	0.603 (7)	0.046 (11)*	0.044 (5)
C23P	0.398 (4)	0.0531 (18)	0.454 (7)	0.046 (15)*	0.044 (5)
H23P	0.4191	0.0491	0.3189	0.055*	0.044 (5)
C24P	0.323 (5)	0.087 (2)	0.504 (9)	0.072 (18)*	0.044 (5)
H24P	0.2948	0.1060	0.4044	0.086*	0.044 (5)
C25P	0.290 (5)	0.092 (2)	0.704 (9)	0.06 (3)*	0.044 (5)
H25P	0.2383	0.1143	0.7384	0.074*	0.044 (5)
C26P	0.332 (7)	0.065 (3)	0.853 (7)	0.09 (2)*	0.044 (5)
H26P	0.3086	0.0683	0.9877	0.108*	0.044 (5)
C27P	0.411 (6)	0.031 (2)	0.802 (6)	0.06 (3)*	0.044 (5)
H27P	0.4416	0.0132	0.9031	0.075*	0.044 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1R	0.130 (3)	0.0559 (16)	0.0653 (17)	0.0240 (17)	−0.0373 (18)	−0.0176 (14)
C1R	0.092 (3)	0.047 (2)	0.059 (2)	0.0165 (19)	−0.036 (2)	−0.0054 (17)
C2R	0.134 (4)	0.067 (3)	0.055 (2)	0.018 (3)	0.028 (2)	0.0191 (19)
C3R	0.071 (3)	0.061 (3)	0.137 (4)	−0.007 (2)	0.022 (3)	0.023 (3)
C4R	0.065 (2)	0.056 (2)	0.102 (4)	−0.0031 (19)	−0.033 (3)	0.011 (2)
C5R	0.080 (3)	0.0386 (17)	0.0392 (17)	0.0065 (17)	−0.0083 (17)	−0.0027 (14)
C6R	0.138 (4)	0.040 (2)	0.055 (2)	0.010 (2)	−0.011 (3)	−0.0086 (18)
C7R	0.099 (3)	0.0346 (17)	0.075 (3)	0.0123 (19)	−0.016 (2)	−0.0079 (18)
C8R	0.101 (4)	0.049 (2)	0.134 (4)	−0.009 (2)	−0.026 (3)	0.027 (3)
C9R	0.097 (3)	0.0418 (19)	0.087 (3)	0.019 (2)	−0.035 (3)	0.002 (2)
C10R	0.0456 (19)	0.0373 (16)	0.0577 (19)	0.0087 (14)	−0.0041 (17)	−0.0083 (15)
C11R	0.067 (2)	0.0370 (17)	0.0496 (18)	0.0094 (15)	−0.0050 (16)	−0.0055 (15)
C12R	0.063 (2)	0.0320 (15)	0.0419 (18)	0.0041 (14)	−0.0049 (16)	0.0007 (14)
C13R	0.069 (2)	0.0367 (17)	0.0363 (16)	0.0056 (17)	0.0100 (16)	0.0028 (15)
C14R	0.0571 (19)	0.0349 (18)	0.0441 (17)	0.0065 (16)	0.0112 (15)	0.0031 (15)
C15R	0.0435 (17)	0.0314 (15)	0.0347 (15)	0.0028 (13)	0.0001 (14)	0.0015 (13)
C16R	0.058 (2)	0.0396 (17)	0.0347 (16)	0.0036 (15)	0.0052 (18)	−0.0014 (14)
C17R	0.061 (2)	0.0355 (17)	0.0490 (18)	0.0149 (16)	0.0064 (19)	−0.0047 (16)
C18R	0.0461 (18)	0.0335 (16)	0.0408 (18)	−0.0017 (14)	−0.0024 (14)	0.0039 (15)
C19R	0.065 (3)	0.071 (3)	0.186 (6)	0.004 (2)	0.034 (4)	−0.015 (4)
O2R	0.090 (2)	0.0442 (18)	0.0416 (15)	0.0091 (17)	0.0014 (13)	0.0102 (13)
O3R	0.078 (2)	0.046 (2)	0.0465 (17)	0.025 (2)	−0.0050 (12)	−0.0019 (14)
N1R	0.0554 (16)	0.0378 (16)	0.0412 (14)	0.0145 (13)	−0.0015 (12)	0.0024 (14)
C20R	0.067 (2)	0.0365 (17)	0.058 (2)	0.0047 (16)	0.0024 (19)	0.0031 (17)
C21R	0.089 (3)	0.065 (3)	0.083 (3)	−0.007 (2)	−0.006 (3)	−0.020 (2)
C22R	0.0534 (19)	0.0490 (19)	0.060 (2)	−0.0077 (15)	0.0061 (18)	−0.0051 (17)
C23R	0.061 (2)	0.051 (2)	0.111 (4)	0.0091 (18)	0.017 (2)	0.021 (2)
C24R	0.056 (3)	0.066 (3)	0.184 (7)	0.009 (2)	0.007 (4)	0.016 (3)
C25R	0.063 (3)	0.108 (5)	0.168 (7)	0.005 (3)	0.028 (4)	−0.033 (5)
C26R	0.073 (3)	0.151 (6)	0.103 (4)	−0.007 (4)	0.028 (3)	−0.026 (4)
C27R	0.068 (3)	0.095 (3)	0.074 (3)	−0.008 (3)	0.011 (2)	0.004 (3)

Geometric parameters (Å, º)

O1R—C11R	1.224 (4)	C5P—C10P	1.557 (10)
C1R—C2R	1.508 (6)	C6P—C7P	1.538 (19)
C1R—C9R	1.514 (5)	C7P—C9P	1.494 (10)
C1R—C10R	1.547 (5)	C7P—C8P	1.525 (19)
C2R—C3R	1.517 (2)	C10P—C19P	1.488 (13)
C3R—C4R	1.519 (6)	C10P—C11P	1.561 (10)
C3R—C8R	1.547 (6)	C11P—C12P	1.509 (7)
C4R—C5R	1.499 (5)	C12P—C17P	1.374 (8)
C5R—C10R	1.517 (5)	C12P—C13P	1.378 (8)
C5R—C6R	1.528 (5)	C13P—C14P	1.382 (7)
C6R—C7R	1.523 (6)	C14P—C15P	1.388 (8)
C7R—C8R	1.497 (6)	C15P—C16P	1.393 (8)
C7R—C9R	1.498 (5)	C15P—C18P	1.476 (16)
C10R—C11R	1.523 (4)	C16P—C17P	1.372 (7)
C10R—C19R	1.539 (5)	C18P—O2P	1.254 (10)
C11R—C12R	1.506 (4)	C18P—O3P	1.265 (10)
C12R—C13R	1.379 (4)	N1R—C20R	1.479 (4)
C12R—C17R	1.381 (4)	C20R—C22R	1.492 (4)
C13R—C14R	1.369 (4)	C20R—C21R	1.531 (5)
C14R—C15R	1.387 (4)	C22R—C23R	1.372 (4)
C15R—C16R	1.378 (4)	C22R—C27R	1.382 (5)
C15R—C18R	1.497 (5)	C23R—C24R	1.390 (5)
C16R—C17R	1.382 (4)	C24R—C25R	1.338 (6)
C18R—O2R	1.241 (4)	C25R—C26R	1.345 (6)
C18R—O3R	1.267 (4)	C26R—C27R	1.382 (5)
O1P—C11P	1.462 (18)	N1P—C20P	1.48 (2)
C1P—C9P	1.507 (10)	C20P—C22P	1.498 (14)
C1P—C2P	1.529 (10)	C20P—C21P	1.51 (2)
C1P—C10P	1.551 (10)	C22P—C27P	1.365 (9)
C2P—C3P	1.483 (18)	C22P—C23P	1.385 (9)
C2P—C11P	1.518 (10)	C23P—C24P	1.375 (9)
C3P—C4P	1.509 (10)	C24P—C25P	1.374 (9)
C3P—C8P	1.522 (19)	C25P—C26P	1.358 (9)
C4P—C5P	1.527 (10)	C26P—C27P	1.400 (9)
C5P—C6P	1.551 (10)
C2R—C1R—C9R	109.4 (4)	C9P—C7P—C8P	106.1 (16)
C2R—C1R—C10R	109.1 (3)	C9P—C7P—C6P	107 (2)
C9R—C1R—C10R	111.3 (3)	C8P—C7P—C6P	114 (2)
C1R—C2R—C3R	109.4 (3)	C3P—C8P—C7P	109.6 (18)
C2R—C3R—C4R	108.7 (3)	C7P—C9P—C1P	107.5 (15)
C2R—C3R—C8R	109.6 (4)	C19P—C10P—C1P	118.0 (15)
C4R—C3R—C8R	109.0 (4)	C19P—C10P—C5P	113.1 (10)
C5R—C4R—C3R	110.0 (3)	C1P—C10P—C5P	107.8 (15)
C4R—C5R—C10R	110.8 (3)	C19P—C10P—C11P	120.7 (11)
C4R—C5R—C6R	108.2 (3)	C1P—C10P—C11P	83.4 (9)
C10R—C5R—C6R	110.4 (3)	C5P—C10P—C11P	110 (2)
C7R—C6R—C5R	110.2 (3)	O1P—C11P—C12P	106.1 (19)
C8R—C7R—C9R	109.2 (4)	O1P—C11P—C2P	105 (2)
C8R—C7R—C6R	108.5 (4)	C12P—C11P—C2P	124.7 (9)
C9R—C7R—C6R	110.0 (3)	O1P—C11P—C10P	107 (2)
C7R—C8R—C3R	109.4 (3)	C12P—C11P—C10P	125.4 (9)
C7R—C9R—C1R	110.2 (3)	C2P—C11P—C10P	85.5 (7)
C5R—C10R—C11R	114.8 (3)	C17P—C12P—C13P	118.1 (5)
C5R—C10R—C19R	112.1 (4)	C17P—C12P—C11P	122.2 (8)
C11R—C10R—C19R	102.7 (3)	C13P—C12P—C11P	119.7 (8)
C5R—C10R—C1R	107.0 (3)	C12P—C13P—C14P	120.9 (5)
C11R—C10R—C1R	109.3 (3)	C13P—C14P—C15P	121.0 (5)
C19R—C10R—C1R	110.9 (4)	C14P—C15P—C16P	117.7 (5)
O1R—C11R—C12R	116.2 (3)	C14P—C15P—C18P	121 (2)
O1R—C11R—C10R	118.8 (3)	C16P—C15P—C18P	122 (2)
C12R—C11R—C10R	125.0 (3)	C17P—C16P—C15P	120.4 (5)
C13R—C12R—C17R	118.9 (3)	C16P—C17P—C12P	121.9 (5)
C13R—C12R—C11R	116.2 (3)	O2P—C18P—O3P	121 (3)
C17R—C12R—C11R	124.7 (3)	O2P—C18P—C15P	119.0 (19)
C14R—C13R—C12R	121.1 (2)	O3P—C18P—C15P	118.2 (19)
C13R—C14R—C15R	120.5 (2)	N1R—C20R—C22R	111.0 (3)
C16R—C15R—C14R	118.3 (3)	N1R—C20R—C21R	108.3 (3)
C16R—C15R—C18R	120.9 (3)	C22R—C20R—C21R	114.5 (3)
C14R—C15R—C18R	120.8 (2)	C23R—C22R—C27R	117.7 (3)
C15R—C16R—C17R	121.3 (2)	C23R—C22R—C20R	122.3 (3)
C12R—C17R—C16R	119.8 (2)	C27R—C22R—C20R	119.9 (3)
O2R—C18R—O3R	124.6 (4)	C22R—C23R—C24R	120.8 (4)
O2R—C18R—C15R	118.8 (3)	C25R—C24R—C23R	119.6 (4)
O3R—C18R—C15R	116.6 (3)	C24R—C25R—C26R	121.6 (4)
C9P—C1P—C2P	120.4 (11)	C25R—C26R—C27R	119.5 (4)
C9P—C1P—C10P	119.9 (11)	C22R—C27R—C26R	120.9 (4)
C2P—C1P—C10P	85.5 (7)	N1P—C20P—C22P	111 (3)
C3P—C2P—C11P	116.7 (19)	N1P—C20P—C21P	108 (3)
C3P—C2P—C1P	110.6 (16)	C22P—C20P—C21P	112 (3)
C11P—C2P—C1P	85.6 (9)	C27P—C22P—C23P	119.2 (7)
C2P—C3P—C4P	109 (2)	C27P—C22P—C20P	121.1 (13)
C2P—C3P—C8P	112 (2)	C23P—C22P—C20P	119.7 (13)
C4P—C3P—C8P	108 (2)	C24P—C23P—C22P	120.8 (8)
C3P—C4P—C5P	104.4 (17)	C25P—C24P—C23P	119.1 (8)
C4P—C5P—C6P	106.1 (9)	C26P—C25P—C24P	121.2 (8)
C4P—C5P—C10P	111 (2)	C25P—C26P—C27P	119.3 (8)
C6P—C5P—C10P	111 (2)	C22P—C27P—C26P	120.4 (8)
C7P—C6P—C5P	109.8 (18)

(10.6P)

Crystal data

C27H33NO3	Dx = 1.213 Mg m^−3
Mr = 419.54	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 2444 reflections
a = 11.7903 (11) Å	θ = 6–21°
b = 29.728 (2) Å	µ = 0.08 mm^−1
c = 6.5519 (5) Å	T = 293 K
V = 2296.5 (3) Å^3	Block, colourless
Z = 4	0.56 × 0.41 × 0.20 mm
F(000) = 904

Data collection

Kuma KM4CCD diffractometer	3308 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.055
Graphite monochromator	θmax = 25.0°, θmin = 6.0°
ω scans	h = −13→14
10693 measured reflections	k = −35→35
3970 independent reflections	l = −7→6

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.071	w = 1/[σ^2(Fo^2) + (0.045P)^2 + 1.4328P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.150	(Δ/σ)max = 0.003
S = 1.05	Δρmax = 0.16 e Å^−3
3970 reflections	Δρmin = −0.16 e Å^−3
406 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
276 restraints	Extinction coefficient: 0.033 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: The absolute configuration was assigned to agree with that from Leibovitch M. et all, 1997; 1998
Secondary atom site location: inferred from neighbouring sites

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1R	0.4146 (4)	0.21049 (11)	0.4790 (5)	0.0866 (13)	0.894 (6)
C1R	0.4129 (6)	0.30208 (19)	0.5275 (7)	0.0641 (18)	0.894 (6)
H1R	0.3645	0.2896	0.4198	0.077*	0.894 (6)
C2R	0.5335 (5)	0.30493 (17)	0.4500 (7)	0.0901 (18)	0.894 (6)
H2AR	0.5360	0.3232	0.3273	0.108*	0.894 (6)
H2BR	0.5609	0.2751	0.4163	0.108*	0.894 (6)
C3R	0.6084 (5)	0.3257 (2)	0.6131 (9)	0.098 (2)	0.894 (6)
H3R	0.6864	0.3282	0.5627	0.117*	0.894 (6)
C4R	0.6053 (4)	0.29542 (17)	0.7996 (9)	0.0807 (17)	0.894 (6)
H4AR	0.6339	0.2658	0.7643	0.097*	0.894 (6)
H4BR	0.6534	0.3078	0.9056	0.097*	0.894 (6)
C5R	0.4861 (5)	0.29154 (14)	0.8767 (6)	0.0581 (13)	0.894 (6)
H5R	0.4853	0.2726	0.9992	0.070*	0.894 (6)
C6R	0.4426 (6)	0.33876 (17)	0.9315 (8)	0.0848 (19)	0.894 (6)
H6AR	0.3660	0.3367	0.9847	0.102*	0.894 (6)
H6BR	0.4904	0.3518	1.0365	0.102*	0.894 (6)
C7R	0.4436 (5)	0.36879 (13)	0.7436 (8)	0.0774 (15)	0.894 (6)
H7R	0.4149	0.3987	0.7794	0.093*	0.894 (6)
C8R	0.5628 (5)	0.37247 (16)	0.6701 (10)	0.102 (2)	0.894 (6)
H8AR	0.6097	0.3855	0.7762	0.122*	0.894 (6)
H8BR	0.5657	0.3921	0.5518	0.122*	0.894 (6)
C9R	0.3718 (6)	0.34895 (15)	0.5798 (12)	0.0815 (17)	0.894 (6)
H9AR	0.3750	0.3678	0.4592	0.098*	0.894 (6)
H9BR	0.2935	0.3476	0.6253	0.098*	0.894 (6)
C10R	0.4089 (4)	0.27074 (12)	0.7150 (7)	0.0509 (11)	0.894 (6)
C11R	0.4440 (4)	0.22373 (14)	0.6494 (6)	0.0558 (12)	0.894 (6)
C12R	0.5032 (4)	0.18992 (13)	0.7814 (7)	0.0510 (15)	0.894 (6)
C13R	0.5831 (5)	0.16323 (19)	0.6870 (7)	0.0532 (16)	0.894 (6)
H13R	0.6025	0.1689	0.5518	0.064*	0.894 (6)
C14R	0.6346 (4)	0.12854 (16)	0.7886 (7)	0.0486 (13)	0.894 (6)
H14R	0.6892	0.1113	0.7228	0.058*	0.894 (6)
C15R	0.6057 (6)	0.1191 (2)	0.9892 (8)	0.0395 (18)	0.894 (6)
C16R	0.5293 (7)	0.14695 (18)	1.0866 (9)	0.0473 (18)	0.894 (6)
H16R	0.5115	0.1417	1.2228	0.057*	0.894 (6)
C17R	0.4788 (7)	0.1826 (2)	0.9850 (9)	0.0514 (18)	0.894 (6)
H17R	0.4287	0.2014	1.0534	0.062*	0.894 (6)
C18R	0.6562 (6)	0.0794 (2)	1.0966 (8)	0.0438 (17)	0.894 (6)
C19R	0.2862 (4)	0.2645 (2)	0.7912 (13)	0.111 (2)	0.894 (6)
H19A	0.2577	0.2926	0.8411	0.166*	0.894 (6)
H19B	0.2851	0.2427	0.8992	0.166*	0.894 (6)
H19C	0.2395	0.2542	0.6806	0.166*	0.894 (6)
O2R	0.6539 (9)	0.0783 (2)	1.2865 (8)	0.0628 (15)	0.894 (6)
O3R	0.6989 (10)	0.0489 (3)	0.9856 (10)	0.059 (2)	0.894 (6)
O1P	0.358 (4)	0.2108 (14)	0.525 (7)	0.155 (19)*	0.106 (6)
HO1P	0.3918	0.1935	0.4488	0.232*	0.106 (6)
C1P	0.395 (2)	0.2945 (9)	0.541 (4)	0.11 (4)*	0.106 (6)
H1P	0.3380	0.2821	0.4476	0.137*	0.106 (6)
C2P	0.502 (2)	0.2661 (8)	0.530 (4)	0.097 (15)*	0.106 (6)
H2P	0.5229	0.2556	0.3935	0.117*	0.106 (6)
C3P	0.595 (2)	0.2895 (10)	0.644 (4)	0.061 (10)*	0.106 (6)
H3P	0.6676	0.2755	0.6077	0.073*	0.106 (6)
C4P	0.578 (3)	0.2851 (11)	0.871 (4)	0.056 (11)*	0.106 (6)
H4AP	0.6297	0.3044	0.9449	0.067*	0.106 (6)
H4BP	0.5893	0.2543	0.9149	0.067*	0.106 (6)
C5P	0.455 (2)	0.2996 (11)	0.908 (4)	0.070 (15)*	0.106 (6)
H5P	0.4327	0.2925	1.0489	0.084*	0.106 (6)
C6P	0.452 (3)	0.3512 (10)	0.874 (6)	0.074 (18)*	0.106 (6)
H6AP	0.3761	0.3625	0.8962	0.089*	0.106 (6)
H6BP	0.5025	0.3658	0.9708	0.089*	0.106 (6)
C7P	0.491 (3)	0.3620 (10)	0.653 (6)	0.093 (18)*	0.106 (6)
H7P	0.4985	0.3946	0.6363	0.111*	0.106 (6)
C8P	0.599 (3)	0.3387 (11)	0.585 (7)	0.12 (2)*	0.106 (6)
H8AP	0.6072	0.3415	0.4386	0.149*	0.106 (6)
H8BP	0.6638	0.3529	0.6493	0.149*	0.106 (6)
C9P	0.399 (3)	0.3447 (9)	0.517 (6)	0.09 (3)*	0.106 (6)
H9AP	0.4151	0.3526	0.3765	0.111*	0.106 (6)
H9BP	0.3268	0.3579	0.5550	0.111*	0.106 (6)
C10P	0.379 (2)	0.2733 (8)	0.756 (4)	0.064 (15)*	0.106 (6)
C11P	0.440 (2)	0.2320 (7)	0.663 (4)	0.080 (11)*	0.106 (6)
C12P	0.497 (2)	0.1946 (7)	0.779 (4)	0.036 (9)*	0.106 (6)
C13P	0.590 (3)	0.1734 (10)	0.694 (5)	0.030 (11)*	0.106 (6)
H13P	0.6166	0.1826	0.5673	0.036*	0.106 (6)
C14P	0.644 (3)	0.1387 (11)	0.795 (6)	0.033 (9)*	0.106 (6)
H14P	0.7058	0.1246	0.7340	0.039*	0.106 (6)
C15P	0.607 (4)	0.1243 (16)	0.985 (7)	0.036 (15)*	0.106 (6)
C16P	0.513 (5)	0.1457 (19)	1.069 (7)	0.07 (3)*	0.106 (6)
H16P	0.4854	0.1367	1.1958	0.089*	0.106 (6)
C17P	0.459 (4)	0.1797 (17)	0.965 (6)	0.05 (2)*	0.106 (6)
H17P	0.3957	0.1932	1.0228	0.061*	0.106 (6)
C18P	0.664 (5)	0.0866 (15)	1.092 (7)	0.048 (17)*	0.106 (6)
C19P	0.258 (2)	0.2700 (14)	0.826 (7)	0.14 (2)*	0.106 (6)
H19D	0.2555	0.2565	0.9591	0.210*	0.106 (6)
H19E	0.2156	0.2517	0.7318	0.210*	0.106 (6)
H19F	0.2250	0.2995	0.8319	0.210*	0.106 (6)
O2P	0.657 (6)	0.085 (2)	1.283 (7)	0.056 (10)*	0.106 (6)
O3P	0.711 (8)	0.056 (2)	0.987 (9)	0.056 (18)*	0.106 (6)
N1R	0.6524 (4)	0.01734 (14)	0.5946 (8)	0.0460 (10)	0.894 (6)
H1NR	0.7037	−0.0004	0.5363	0.069*	0.894 (6)
H2NR	0.6747	0.0242	0.7206	0.069*	0.894 (6)
H3NR	0.6451	0.0424	0.5218	0.069*	0.894 (6)
C20R	0.5417 (5)	−0.00632 (16)	0.6033 (10)	0.0554 (15)	0.894 (6)
H20R	0.5488	−0.0309	0.7020	0.067*	0.894 (6)
C21R	0.5185 (5)	−0.02724 (19)	0.3930 (10)	0.0801 (17)	0.894 (6)
H21A	0.5824	−0.0452	0.3524	0.120*	0.894 (6)
H21B	0.5065	−0.0038	0.2947	0.120*	0.894 (6)
H21C	0.4522	−0.0459	0.4004	0.120*	0.894 (6)
C22R	0.4504 (4)	0.02450 (14)	0.6772 (8)	0.0564 (11)	0.894 (6)
C23R	0.4196 (4)	0.06258 (15)	0.5713 (9)	0.0736 (14)	0.894 (6)
H23R	0.4544	0.0690	0.4473	0.088*	0.894 (6)
C24R	0.3372 (4)	0.09148 (18)	0.6475 (12)	0.102 (2)	0.894 (6)
H24R	0.3186	0.1176	0.5769	0.122*	0.894 (6)
C25R	0.2848 (5)	0.0815 (2)	0.8225 (13)	0.111 (2)	0.894 (6)
H25R	0.2290	0.1008	0.8720	0.134*	0.894 (6)
C26R	0.3113 (5)	0.0440 (3)	0.9293 (10)	0.108 (2)	0.894 (6)
H26R	0.2736	0.0375	1.0504	0.129*	0.894 (6)
C27R	0.3941 (4)	0.0155 (2)	0.8578 (8)	0.0799 (16)	0.894 (6)
H27R	0.4126	−0.0101	0.9320	0.096*	0.894 (6)
N1P	0.644 (3)	0.0049 (11)	0.608 (6)	0.033 (8)*	0.106 (6)
H1NP	0.6939	−0.0160	0.5709	0.049*	0.106 (6)
H2NP	0.6480	0.0091	0.7423	0.049*	0.106 (6)
H3NP	0.6592	0.0305	0.5439	0.049*	0.106 (6)
C20P	0.527 (3)	−0.0103 (11)	0.553 (5)	0.035 (13)*	0.106 (6)
H20P	0.5103	−0.0383	0.6263	0.041*	0.106 (6)
C21P	0.530 (5)	−0.020 (2)	0.326 (6)	0.104 (19)*	0.106 (6)
H21D	0.5931	−0.0388	0.2941	0.156*	0.106 (6)
H21E	0.5365	0.0081	0.2523	0.156*	0.106 (6)
H21F	0.4606	−0.0346	0.2863	0.156*	0.106 (6)
C22P	0.4427 (19)	0.0250 (8)	0.614 (4)	0.041 (9)*	0.106 (6)
C23P	0.402 (2)	0.0547 (9)	0.468 (3)	0.052 (10)*	0.106 (6)
H23P	0.4264	0.0522	0.3334	0.062*	0.106 (6)
C24P	0.326 (3)	0.0878 (10)	0.520 (4)	0.059 (11)*	0.106 (6)
H24P	0.3015	0.1084	0.4226	0.071*	0.106 (6)
C25P	0.286 (4)	0.0900 (15)	0.717 (5)	0.11 (3)*	0.106 (6)
H25P	0.2309	0.1110	0.7498	0.136*	0.106 (6)
C26P	0.327 (3)	0.0622 (13)	0.864 (4)	0.062 (11)*	0.106 (6)
H26P	0.3031	0.0652	0.9984	0.075*	0.106 (6)
C27P	0.406 (4)	0.0289 (13)	0.810 (4)	0.083 (19)*	0.106 (6)
H27P	0.4329	0.0092	0.9093	0.099*	0.106 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1R	0.134 (4)	0.0592 (18)	0.067 (2)	0.022 (2)	−0.040 (2)	−0.0187 (16)
C1R	0.088 (4)	0.047 (2)	0.057 (3)	0.018 (2)	−0.033 (2)	−0.0035 (19)
C2R	0.131 (5)	0.077 (3)	0.063 (3)	0.023 (3)	0.024 (3)	0.021 (2)
C3R	0.071 (3)	0.084 (4)	0.137 (5)	−0.014 (3)	0.015 (3)	0.023 (4)
C4R	0.068 (3)	0.058 (3)	0.116 (5)	−0.008 (2)	−0.038 (3)	0.011 (3)
C5R	0.090 (4)	0.044 (2)	0.040 (2)	0.009 (2)	−0.010 (2)	−0.0028 (17)
C6R	0.154 (6)	0.043 (3)	0.057 (3)	0.011 (3)	−0.007 (3)	−0.009 (3)
C7R	0.113 (4)	0.036 (2)	0.084 (4)	0.012 (2)	−0.019 (3)	−0.008 (2)
C8R	0.107 (5)	0.056 (3)	0.142 (5)	−0.012 (3)	−0.030 (4)	0.032 (3)
C9R	0.107 (4)	0.044 (3)	0.094 (4)	0.019 (3)	−0.042 (4)	−0.002 (3)
C10R	0.047 (2)	0.040 (2)	0.066 (3)	0.0089 (17)	−0.002 (2)	−0.0079 (18)
C11R	0.067 (3)	0.045 (2)	0.056 (2)	0.0143 (19)	−0.0065 (19)	−0.0043 (18)
C12R	0.066 (3)	0.037 (2)	0.050 (2)	0.0083 (17)	−0.0042 (18)	0.0010 (16)
C13R	0.080 (4)	0.039 (2)	0.041 (2)	0.007 (2)	0.011 (2)	0.002 (2)
C14R	0.061 (3)	0.034 (2)	0.051 (2)	0.010 (2)	0.0116 (19)	0.001 (2)
C15R	0.048 (3)	0.032 (2)	0.038 (2)	0.0019 (18)	0.0019 (15)	0.0006 (16)
C16R	0.062 (3)	0.040 (3)	0.040 (2)	0.0036 (19)	0.011 (2)	−0.0025 (16)
C17R	0.063 (3)	0.034 (2)	0.057 (3)	0.016 (2)	0.009 (3)	−0.004 (2)
C18R	0.047 (3)	0.036 (2)	0.049 (3)	−0.005 (2)	−0.0022 (16)	0.0033 (19)
C19R	0.065 (3)	0.080 (3)	0.187 (7)	0.003 (3)	0.034 (4)	−0.013 (4)
O2R	0.098 (3)	0.046 (3)	0.0446 (17)	0.009 (2)	0.0021 (14)	0.0111 (15)
O3R	0.077 (4)	0.045 (3)	0.053 (2)	0.026 (4)	−0.0025 (17)	−0.0010 (18)
N1R	0.056 (2)	0.035 (2)	0.0473 (19)	0.0128 (17)	−0.0022 (14)	0.0042 (19)
C20R	0.070 (4)	0.038 (2)	0.058 (3)	0.0004 (19)	−0.001 (3)	0.001 (2)
C21R	0.090 (4)	0.069 (3)	0.082 (4)	−0.011 (3)	−0.003 (3)	−0.017 (3)
C22R	0.053 (2)	0.053 (2)	0.063 (3)	−0.0043 (18)	0.001 (2)	−0.002 (2)
C23R	0.064 (3)	0.057 (3)	0.101 (4)	0.010 (2)	0.015 (3)	0.016 (3)
C24R	0.062 (3)	0.072 (3)	0.172 (7)	0.009 (3)	0.001 (5)	0.021 (4)
C25R	0.066 (4)	0.108 (5)	0.161 (8)	0.013 (3)	0.026 (4)	−0.021 (6)
C26R	0.072 (4)	0.148 (7)	0.103 (5)	−0.008 (4)	0.032 (3)	−0.017 (5)
C27R	0.069 (3)	0.099 (4)	0.071 (3)	−0.011 (3)	0.012 (3)	0.011 (3)

Geometric parameters (Å, º)

O1R—C11R	1.233 (5)	C5P—C10P	1.554 (10)
C1R—C2R	1.512 (8)	C6P—C7P	1.549 (19)
C1R—C9R	1.514 (7)	C7P—C9P	1.492 (10)
C1R—C10R	1.543 (7)	C7P—C8P	1.519 (19)
C2R—C3R	1.518 (2)	C10P—C19P	1.499 (13)
C3R—C4R	1.518 (7)	C10P—C11P	1.552 (10)
C3R—C8R	1.537 (8)	C11P—C12P	1.508 (7)
C4R—C5R	1.497 (6)	C12P—C17P	1.374 (8)
C5R—C10R	1.528 (5)	C12P—C13P	1.378 (8)
C5R—C6R	1.537 (6)	C13P—C14P	1.380 (7)
C6R—C7R	1.521 (7)	C14P—C15P	1.390 (8)
C7R—C9R	1.489 (6)	C15P—C16P	1.393 (8)
C7R—C8R	1.489 (7)	C15P—C18P	1.482 (9)
C10R—C11R	1.519 (5)	C16P—C17P	1.371 (7)
C10R—C19R	1.542 (7)	C18P—O2P	1.254 (10)
C11R—C12R	1.498 (5)	C18P—O3P	1.263 (10)
C12R—C13R	1.379 (5)	N1R—C20R	1.483 (6)
C12R—C17R	1.382 (4)	C20R—C22R	1.494 (5)
C13R—C14R	1.370 (5)	C20R—C21R	1.537 (7)
C14R—C15R	1.386 (4)	C22R—C23R	1.376 (5)
C15R—C16R	1.380 (4)	C22R—C27R	1.383 (6)
C15R—C18R	1.497 (5)	C23R—C24R	1.390 (6)
C16R—C17R	1.385 (4)	C24R—C25R	1.336 (7)
C18R—O2R	1.245 (4)	C25R—C26R	1.353 (7)
C18R—O3R	1.267 (5)	C26R—C27R	1.375 (6)
O1P—C11P	1.458 (18)	N1P—C20P	1.490 (19)
C1P—C9P	1.502 (10)	C20P—C22P	1.502 (14)
C1P—C2P	1.526 (10)	C20P—C21P	1.518 (19)
C1P—C10P	1.553 (10)	C22P—C27P	1.364 (9)
C2P—C3P	1.492 (17)	C22P—C23P	1.387 (9)
C2P—C11P	1.525 (9)	C23P—C24P	1.374 (9)
C3P—C4P	1.509 (10)	C24P—C25P	1.374 (9)
C3P—C8P	1.513 (19)	C25P—C26P	1.359 (9)
C4P—C5P	1.529 (10)	C26P—C27P	1.402 (9)
C5P—C6P	1.551 (10)
C2R—C1R—C9R	109.0 (6)	C9P—C7P—C8P	106.0 (15)
C2R—C1R—C10R	109.2 (3)	C9P—C7P—C6P	106 (2)
C9R—C1R—C10R	111.5 (4)	C8P—C7P—C6P	115 (2)
C1R—C2R—C3R	109.5 (4)	C3P—C8P—C7P	110.0 (18)
C4R—C3R—C2R	108.2 (4)	C7P—C9P—C1P	107.7 (14)
C4R—C3R—C8R	109.4 (5)	C19P—C10P—C11P	120.7 (11)
C2R—C3R—C8R	109.6 (5)	C19P—C10P—C1P	114.9 (14)
C5R—C4R—C3R	109.9 (4)	C11P—C10P—C1P	84.6 (8)
C4R—C5R—C10R	110.9 (4)	C19P—C10P—C5P	112.8 (9)
C4R—C5R—C6R	108.8 (4)	C11P—C10P—C5P	112.4 (17)
C10R—C5R—C6R	109.4 (4)	C1P—C10P—C5P	107.9 (14)
C7R—C6R—C5R	110.1 (4)	O1P—C11P—C12P	106.7 (18)
C9R—C7R—C8R	109.4 (6)	O1P—C11P—C2P	104.8 (19)
C9R—C7R—C6R	110.3 (4)	C12P—C11P—C2P	124.1 (8)
C8R—C7R—C6R	108.2 (5)	O1P—C11P—C10P	106.1 (19)
C7R—C8R—C3R	110.0 (4)	C12P—C11P—C10P	126.5 (9)
C7R—C9R—C1R	110.2 (4)	C2P—C11P—C10P	85.5 (6)
C11R—C10R—C5R	114.0 (3)	C17P—C12P—C13P	117.9 (5)
C11R—C10R—C19R	103.6 (4)	C17P—C12P—C11P	122.7 (7)
C5R—C10R—C19R	112.6 (5)	C13P—C12P—C11P	119.3 (6)
C11R—C10R—C1R	108.8 (4)	C12P—C13P—C14P	121.0 (6)
C5R—C10R—C1R	106.9 (3)	C13P—C14P—C15P	120.9 (5)
C19R—C10R—C1R	111.0 (4)	C14P—C15P—C16P	117.6 (5)
O1R—C11R—C12R	116.0 (4)	C14P—C15P—C18P	121.1 (8)
O1R—C11R—C10R	118.3 (4)	C16P—C15P—C18P	121.3 (8)
C12R—C11R—C10R	125.5 (3)	C17P—C16P—C15P	120.5 (5)
C13R—C12R—C17R	118.9 (3)	C16P—C17P—C12P	121.9 (6)
C13R—C12R—C11R	116.5 (3)	O2P—C18P—O3P	123 (2)
C17R—C12R—C11R	124.5 (3)	O2P—C18P—C15P	118.1 (16)
C14R—C13R—C12R	121.2 (3)	O3P—C18P—C15P	118.5 (17)
C13R—C14R—C15R	120.3 (3)	N1R—C20R—C22R	110.8 (4)
C16R—C15R—C14R	118.5 (3)	N1R—C20R—C21R	108.3 (4)
C16R—C15R—C18R	121.0 (3)	C22R—C20R—C21R	114.2 (5)
C14R—C15R—C18R	120.5 (3)	C23R—C22R—C27R	117.6 (4)
C15R—C16R—C17R	121.2 (3)	C23R—C22R—C20R	122.1 (4)
C12R—C17R—C16R	119.7 (3)	C27R—C22R—C20R	120.3 (4)
O2R—C18R—O3R	124.3 (5)	C22R—C23R—C24R	120.8 (4)
O2R—C18R—C15R	118.9 (4)	C25R—C24R—C23R	119.7 (5)
O3R—C18R—C15R	116.9 (3)	C24R—C25R—C26R	121.3 (5)
C9P—C1P—C2P	121.1 (11)	C25R—C26R—C27R	119.7 (5)
C9P—C1P—C10P	120.1 (11)	C26R—C27R—C22R	120.9 (5)
C2P—C1P—C10P	85.5 (7)	N1P—C20P—C22P	109.7 (19)
C3P—C2P—C11P	112.3 (15)	N1P—C20P—C21P	106 (2)
C3P—C2P—C1P	109.2 (14)	C22P—C20P—C21P	113.6 (15)
C11P—C2P—C1P	86.5 (8)	C27P—C22P—C23P	119.1 (7)
C2P—C3P—C4P	110.7 (17)	C27P—C22P—C20P	121.4 (12)
C2P—C3P—C8P	110 (2)	C23P—C22P—C20P	119.5 (12)
C4P—C3P—C8P	110 (2)	C24P—C23P—C22P	120.7 (8)
C3P—C4P—C5P	105.2 (16)	C25P—C24P—C23P	119.3 (8)
C4P—C5P—C6P	105.9 (9)	C26P—C25P—C24P	121.2 (8)
C4P—C5P—C10P	107.7 (18)	C25P—C26P—C27P	119.1 (8)
C6P—C5P—C10P	113.1 (19)	C22P—C27P—C26P	120.5 (8)
C7P—C6P—C5P	109.5 (17)

(26.5P)

Crystal data

C27H33NO3	Dx = 1.212 Mg m^−3
Mr = 419.54	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1918 reflections
a = 11.8470 (13) Å	θ = 6–19°
b = 29.649 (3) Å	µ = 0.08 mm^−1
c = 6.5443 (6) Å	T = 293 K
V = 2298.7 (4) Å^3	Block, colourless
Z = 4	0.56 × 0.41 × 0.20 mm
F(000) = 904

Data collection

Kuma KM4CCD diffractometer	3083 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.071
Graphite monochromator	θmax = 25.0°, θmin = 6.0°
ω scans	h = −13→14
10623 measured reflections	k = −35→35
3972 independent reflections	l = −7→6

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.083	w = 1/[σ^2(Fo^2) + (0.0806P)^2 + 1.2849P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.208	(Δ/σ)max = 0.001
S = 1.08	Δρmax = 0.20 e Å^−3
3972 reflections	Δρmin = −0.16 e Å^−3
406 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
232 restraints	Extinction coefficient: 0.087 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: The absolute configuration was assigned to agree with that from Leibovitch M. et all, 1997; 1998
Secondary atom site location: inferred from neighbouring sites

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1R	0.4111 (8)	0.21199 (17)	0.4754 (9)	0.096 (2)	0.735 (8)
C1R	0.4112 (8)	0.3028 (3)	0.5294 (11)	0.071 (3)	0.735 (8)
H1R	0.3634	0.2904	0.4207	0.085*	0.735 (8)
C2R	0.5322 (8)	0.3073 (3)	0.4524 (11)	0.105 (3)	0.735 (8)
H2AR	0.5612	0.2778	0.4158	0.126*	0.735 (8)
H2BR	0.5334	0.3261	0.3310	0.126*	0.735 (8)
C3R	0.6063 (7)	0.3280 (3)	0.6141 (15)	0.109 (4)	0.735 (8)
H3R	0.6835	0.3313	0.5626	0.131*	0.735 (8)
C4R	0.6046 (6)	0.2956 (3)	0.7967 (15)	0.092 (3)	0.735 (8)
H4AR	0.6313	0.2661	0.7545	0.111*	0.735 (8)
H4BR	0.6544	0.3068	0.9029	0.111*	0.735 (8)
C5R	0.4864 (7)	0.2918 (2)	0.8784 (10)	0.070 (3)	0.735 (8)
H5R	0.4863	0.2729	1.0014	0.084*	0.735 (8)
C6R	0.4421 (10)	0.3397 (3)	0.9316 (13)	0.098 (3)	0.735 (8)
H6AR	0.3660	0.3374	0.9852	0.118*	0.735 (8)
H6BR	0.4895	0.3529	1.0366	0.118*	0.735 (8)
C7R	0.4422 (8)	0.3692 (2)	0.7481 (12)	0.091 (3)	0.735 (8)
H7R	0.4134	0.3992	0.7847	0.110*	0.735 (8)
C8R	0.5604 (8)	0.3731 (3)	0.6774 (15)	0.111 (3)	0.735 (8)
H8AR	0.6065	0.3854	0.7866	0.133*	0.735 (8)
H8BR	0.5640	0.3938	0.5626	0.133*	0.735 (8)
C9R	0.3719 (10)	0.3497 (2)	0.5824 (18)	0.101 (3)	0.735 (8)
H9AR	0.3766	0.3688	0.4622	0.122*	0.735 (8)
H9BR	0.2937	0.3487	0.6259	0.122*	0.735 (8)
C10R	0.4068 (6)	0.27150 (17)	0.7181 (13)	0.0566 (18)	0.735 (8)
C11R	0.4440 (6)	0.2252 (2)	0.6459 (10)	0.0640 (17)	0.735 (8)
C12R	0.5002 (7)	0.1899 (2)	0.7750 (11)	0.065 (3)	0.735 (8)
C13R	0.5795 (8)	0.1635 (3)	0.6780 (10)	0.063 (3)	0.735 (8)
H13R	0.5992	0.1699	0.5435	0.075*	0.735 (8)
C14R	0.6298 (8)	0.1280 (3)	0.7769 (10)	0.059 (3)	0.735 (8)
H14R	0.6830	0.1105	0.7091	0.070*	0.735 (8)
C15R	0.6018 (10)	0.1182 (3)	0.9769 (11)	0.044 (3)	0.735 (8)
C16R	0.5270 (10)	0.1459 (3)	1.0775 (11)	0.056 (6)	0.735 (8)
H16R	0.5099	0.1403	1.2138	0.067*	0.735 (8)
C17R	0.4770 (11)	0.1822 (3)	0.9789 (12)	0.063 (5)	0.735 (8)
H17R	0.4282	0.2011	1.0495	0.075*	0.735 (8)
C18R	0.6523 (8)	0.0784 (3)	1.0827 (11)	0.047 (3)	0.735 (8)
C19R	0.2854 (6)	0.2653 (3)	0.797 (2)	0.118 (4)	0.735 (8)
H19A	0.2573	0.2936	0.8464	0.177*	0.735 (8)
H19B	0.2849	0.2435	0.9053	0.177*	0.735 (8)
H19C	0.2383	0.2548	0.6871	0.177*	0.735 (8)
O2R	0.6556 (12)	0.0778 (4)	1.2729 (13)	0.088 (5)	0.735 (8)
O3R	0.6996 (14)	0.0489 (4)	0.9717 (16)	0.071 (5)	0.735 (8)
O1P	0.364 (2)	0.2098 (9)	0.540 (4)	0.160 (15)*	0.265 (8)
HO1P	0.3966	0.1923	0.4628	0.241*	0.265 (8)
C1P	0.3967 (15)	0.2954 (6)	0.547 (3)	0.103 (16)*	0.265 (8)
H1P	0.3384	0.2830	0.4563	0.124*	0.265 (8)
C2P	0.5043 (12)	0.2671 (4)	0.528 (2)	0.081 (6)*	0.265 (8)
H2P	0.5224	0.2565	0.3897	0.098*	0.265 (8)
C3P	0.5977 (14)	0.2898 (7)	0.638 (3)	0.081 (6)*	0.265 (8)
H3P	0.6690	0.2755	0.5987	0.098*	0.265 (8)
C4P	0.5837 (18)	0.2855 (8)	0.866 (3)	0.078 (7)*	0.265 (8)
H4AP	0.6378	0.3043	0.9379	0.094*	0.265 (8)
H4BP	0.5938	0.2545	0.9098	0.094*	0.265 (8)
C5P	0.4632 (17)	0.3013 (8)	0.908 (3)	0.092 (11)*	0.265 (8)
H5P	0.4430	0.2947	1.0499	0.110*	0.265 (8)
C6P	0.464 (3)	0.3530 (7)	0.873 (4)	0.143 (19)*	0.265 (8)
H6AP	0.5174	0.3671	0.9652	0.171*	0.265 (8)
H6BP	0.3894	0.3653	0.9027	0.171*	0.265 (8)
C7P	0.496 (2)	0.3634 (8)	0.647 (4)	0.115 (11)*	0.265 (8)
H7P	0.5045	0.3960	0.6270	0.138*	0.265 (8)
C8P	0.602 (2)	0.3391 (9)	0.577 (5)	0.157 (16)*	0.265 (8)
H8AP	0.6677	0.3532	0.6369	0.189*	0.265 (8)
H8BP	0.6081	0.3414	0.4293	0.189*	0.265 (8)
C9P	0.4011 (18)	0.3458 (5)	0.523 (4)	0.096 (11)*	0.265 (8)
H9AP	0.4119	0.3537	0.3803	0.115*	0.265 (8)
H9BP	0.3306	0.3591	0.5687	0.115*	0.265 (8)
C10P	0.3855 (15)	0.2741 (5)	0.762 (3)	0.104 (16)*	0.265 (8)
C11P	0.4475 (14)	0.2331 (5)	0.665 (3)	0.080 (5)*	0.265 (8)
C12P	0.5045 (12)	0.1952 (4)	0.777 (2)	0.040 (5)*	0.265 (8)
C13P	0.5902 (17)	0.1715 (6)	0.685 (3)	0.049 (7)*	0.265 (8)
H13P	0.6128	0.1793	0.5539	0.059*	0.265 (8)
C14P	0.6433 (17)	0.1362 (6)	0.784 (3)	0.039 (6)*	0.265 (8)
H14P	0.7003	0.1204	0.7174	0.047*	0.265 (8)
C15P	0.613 (2)	0.1240 (7)	0.981 (3)	0.045 (10)*	0.265 (8)
C16P	0.525 (3)	0.1478 (10)	1.073 (3)	0.07 (2)*	0.265 (8)
H16P	0.5002	0.1396	1.2025	0.089*	0.265 (8)
C17P	0.474 (2)	0.1829 (9)	0.974 (3)	0.064 (14)*	0.265 (8)
H17P	0.4174	0.1989	1.0399	0.077*	0.265 (8)
C18P	0.668 (2)	0.0854 (6)	1.086 (3)	0.045 (9)*	0.265 (8)
C19P	0.270 (2)	0.2672 (16)	0.844 (5)	0.22 (3)*	0.265 (8)
H19D	0.2745	0.2535	0.9771	0.333*	0.265 (8)
H19E	0.2280	0.2479	0.7543	0.333*	0.265 (8)
H19F	0.2322	0.2958	0.8553	0.333*	0.265 (8)
O2P	0.6514 (19)	0.0801 (9)	1.275 (3)	0.050 (7)*	0.265 (8)
O3P	0.701 (4)	0.0533 (9)	0.975 (5)	0.068 (12)*	0.265 (8)
N1R	0.6524 (8)	0.0183 (3)	0.5771 (16)	0.059 (2)	0.735 (8)
H1NR	0.7049	0.0011	0.5192	0.088*	0.735 (8)
H2NR	0.6740	0.0257	0.7029	0.088*	0.735 (8)
H3NR	0.6430	0.0432	0.5033	0.088*	0.735 (8)
C20R	0.5445 (10)	−0.0068 (3)	0.5868 (18)	0.069 (7)	0.735 (8)
H20R	0.5542	−0.0322	0.6813	0.083*	0.735 (8)
C21R	0.5188 (14)	−0.0260 (5)	0.375 (3)	0.108 (7)	0.735 (8)
H21A	0.5812	−0.0441	0.3296	0.162*	0.735 (8)
H21B	0.5072	−0.0017	0.2801	0.162*	0.735 (8)
H21C	0.4520	−0.0443	0.3810	0.162*	0.735 (8)
C22R	0.4524 (6)	0.0230 (2)	0.6687 (14)	0.064 (3)	0.735 (8)
C23R	0.4219 (6)	0.0617 (2)	0.5667 (15)	0.074 (2)	0.735 (8)
H23R	0.4563	0.0690	0.4433	0.089*	0.735 (8)
C24R	0.3393 (6)	0.0902 (3)	0.6480 (17)	0.099 (3)	0.735 (8)
H24R	0.3211	0.1171	0.5827	0.119*	0.735 (8)
C25R	0.2865 (7)	0.0784 (3)	0.8207 (18)	0.113 (3)	0.735 (8)
H25R	0.2311	0.0973	0.8736	0.136*	0.735 (8)
C26R	0.3117 (7)	0.0395 (4)	0.9211 (14)	0.114 (4)	0.735 (8)
H26R	0.2721	0.0312	1.0380	0.137*	0.735 (8)
C27R	0.3969 (6)	0.0126 (3)	0.8466 (11)	0.081 (2)	0.735 (8)
H27R	0.4174	−0.0132	0.9184	0.097*	0.735 (8)
N1P	0.6521 (16)	0.0103 (8)	0.596 (4)	0.035 (4)*	0.265 (8)
H1NP	0.7025	−0.0104	0.5594	0.052*	0.265 (8)
H2NP	0.6656	0.0189	0.7242	0.052*	0.265 (8)
H3NP	0.6573	0.0340	0.5134	0.052*	0.265 (8)
C20P	0.5371 (17)	−0.0091 (8)	0.583 (4)	0.063 (18)*	0.265 (8)
H20P	0.5326	−0.0329	0.6861	0.076*	0.265 (8)
C21P	0.523 (2)	−0.0316 (12)	0.378 (5)	0.072 (11)*	0.265 (8)
H21D	0.5870	−0.0509	0.3529	0.108*	0.265 (8)
H21E	0.5191	−0.0091	0.2731	0.108*	0.265 (8)
H21F	0.4555	−0.0493	0.3779	0.108*	0.265 (8)
C22P	0.4480 (14)	0.0247 (6)	0.635 (3)	0.069 (10)*	0.265 (8)
C23P	0.410 (2)	0.0553 (8)	0.490 (3)	0.107 (13)*	0.265 (8)
H23P	0.4403	0.0546	0.3583	0.128*	0.265 (8)
C24P	0.329 (2)	0.0867 (8)	0.538 (3)	0.102 (10)*	0.265 (8)
H24P	0.3051	0.1075	0.4406	0.122*	0.265 (8)
C25P	0.284 (2)	0.0871 (9)	0.731 (4)	0.131 (16)*	0.265 (8)
H25P	0.2271	0.1077	0.7627	0.158*	0.265 (8)
C26P	0.320 (2)	0.0579 (9)	0.877 (3)	0.092 (9)*	0.265 (8)
H26P	0.2919	0.0595	1.0093	0.111*	0.265 (8)
C27P	0.400 (2)	0.0252 (9)	0.825 (3)	0.135 (18)*	0.265 (8)
H27P	0.4215	0.0037	0.9208	0.162*	0.265 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1R	0.155 (6)	0.058 (3)	0.075 (3)	0.024 (3)	−0.050 (4)	−0.020 (2)
C1R	0.104 (6)	0.048 (3)	0.062 (4)	0.014 (3)	−0.034 (4)	0.001 (3)
C2R	0.150 (8)	0.091 (5)	0.074 (5)	0.015 (5)	0.027 (5)	0.025 (4)
C3R	0.078 (5)	0.108 (8)	0.142 (9)	−0.012 (5)	0.019 (5)	0.012 (7)
C4R	0.078 (5)	0.070 (5)	0.129 (8)	−0.011 (4)	−0.048 (5)	0.016 (5)
C5R	0.120 (7)	0.044 (3)	0.046 (3)	0.012 (4)	−0.009 (3)	−0.003 (3)
C6R	0.169 (9)	0.054 (4)	0.072 (5)	0.019 (5)	−0.003 (5)	−0.026 (4)
C7R	0.136 (7)	0.038 (3)	0.100 (6)	0.010 (4)	−0.021 (5)	−0.009 (4)
C8R	0.124 (7)	0.064 (5)	0.145 (8)	−0.008 (5)	−0.034 (6)	0.032 (5)
C9R	0.142 (8)	0.048 (4)	0.115 (7)	0.030 (4)	−0.049 (7)	−0.003 (4)
C10R	0.059 (3)	0.040 (3)	0.070 (4)	0.005 (2)	−0.005 (3)	−0.007 (3)
C11R	0.072 (4)	0.052 (3)	0.067 (3)	0.013 (3)	−0.016 (3)	−0.010 (3)
C12R	0.090 (5)	0.041 (3)	0.064 (4)	0.009 (3)	−0.006 (3)	0.003 (3)
C13R	0.097 (6)	0.046 (4)	0.045 (3)	0.005 (4)	0.012 (3)	0.004 (3)
C14R	0.081 (5)	0.034 (3)	0.061 (4)	0.006 (4)	0.015 (3)	−0.002 (3)
C15R	0.060 (5)	0.034 (3)	0.040 (4)	0.002 (3)	0.004 (2)	0.000 (2)
C16R	0.086 (10)	0.038 (4)	0.044 (5)	0.004 (2)	0.018 (3)	−0.002 (2)
C17R	0.080 (7)	0.037 (4)	0.071 (6)	0.022 (3)	0.016 (3)	−0.001 (2)
C18R	0.051 (4)	0.033 (3)	0.056 (5)	−0.009 (3)	0.001 (2)	−0.001 (3)
C19R	0.069 (5)	0.083 (5)	0.202 (11)	−0.002 (4)	0.028 (6)	−0.002 (6)
O2R	0.148 (9)	0.062 (4)	0.053 (3)	0.018 (3)	0.000 (2)	0.015 (2)
O3R	0.097 (7)	0.053 (4)	0.062 (5)	0.036 (4)	−0.002 (2)	0.000 (2)
N1R	0.071 (4)	0.049 (4)	0.057 (4)	0.017 (3)	−0.002 (2)	0.012 (3)
C20R	0.085 (9)	0.044 (5)	0.079 (8)	0.000 (3)	0.004 (3)	0.007 (3)
C21R	0.122 (10)	0.072 (7)	0.130 (11)	−0.016 (5)	−0.022 (6)	−0.024 (6)
C22R	0.055 (4)	0.062 (5)	0.076 (5)	−0.006 (3)	0.004 (3)	0.001 (3)
C23R	0.064 (4)	0.059 (4)	0.100 (6)	0.010 (3)	0.022 (4)	0.016 (4)
C24R	0.072 (5)	0.081 (5)	0.145 (9)	0.012 (4)	−0.002 (6)	0.009 (6)
C25R	0.068 (5)	0.123 (8)	0.148 (10)	0.024 (5)	0.035 (6)	−0.004 (8)
C26R	0.074 (5)	0.155 (10)	0.115 (7)	−0.028 (6)	0.044 (5)	−0.003 (7)
C27R	0.070 (5)	0.101 (6)	0.072 (4)	−0.009 (4)	0.014 (3)	0.012 (4)

Geometric parameters (Å, º)

O1R—C11R	1.246 (7)	C5P—C10P	1.554 (10)
C1R—C9R	1.508 (9)	C6P—C7P	1.561 (18)
C1R—C2R	1.526 (11)	C7P—C9P	1.487 (10)
C1R—C10R	1.546 (10)	C7P—C8P	1.514 (18)
C2R—C3R	1.504 (8)	C10P—C19P	1.488 (15)
C3R—C8R	1.503 (11)	C10P—C11P	1.554 (9)
C3R—C4R	1.533 (9)	C11P—C12P	1.502 (6)
C4R—C5R	1.502 (8)	C12P—C13P	1.375 (7)
C5R—C10R	1.533 (7)	C12P—C17P	1.383 (7)
C5R—C6R	1.553 (9)	C13P—C14P	1.381 (7)
C6R—C7R	1.487 (11)	C14P—C15P	1.390 (7)
C7R—C8R	1.479 (11)	C15P—C16P	1.393 (8)
C7R—C9R	1.484 (8)	C15P—C18P	1.484 (7)
C10R—C11R	1.517 (8)	C16P—C17P	1.365 (7)
C10R—C19R	1.539 (10)	C18P—O2P	1.258 (9)
C11R—C12R	1.502 (6)	C18P—O3P	1.265 (9)
C12R—C13R	1.377 (6)	N1R—C20R	1.481 (10)
C12R—C17R	1.381 (6)	C20R—C22R	1.504 (8)
C13R—C14R	1.372 (6)	C20R—C21R	1.531 (10)
C14R—C15R	1.381 (5)	C22R—C27R	1.372 (7)
C15R—C16R	1.377 (5)	C22R—C23R	1.377 (7)
C15R—C18R	1.494 (6)	C23R—C24R	1.398 (7)
C16R—C17R	1.386 (5)	C24R—C25R	1.338 (8)
C18R—O2R	1.245 (7)	C25R—C26R	1.361 (8)
C18R—O3R	1.268 (7)	C26R—C27R	1.375 (7)
O1P—C11P	1.454 (17)	N1P—C20P	1.481 (10)
C1P—C9P	1.505 (10)	C20P—C22P	1.494 (10)
C1P—C2P	1.530 (10)	C20P—C21P	1.505 (10)
C1P—C10P	1.549 (10)	C22P—C27P	1.367 (8)
C2P—C3P	1.482 (16)	C22P—C23P	1.388 (9)
C2P—C11P	1.509 (9)	C23P—C24P	1.377 (9)
C3P—C4P	1.509 (10)	C24P—C25P	1.374 (9)
C3P—C8P	1.516 (18)	C25P—C26P	1.359 (9)
C4P—C5P	1.526 (10)	C26P—C27P	1.399 (9)
C5P—C6P	1.550 (10)
C9R—C1R—C2R	106.5 (9)	C9P—C7P—C8P	106.9 (14)
C9R—C1R—C10R	111.1 (7)	C9P—C7P—C6P	105.1 (18)
C2R—C1R—C10R	110.4 (5)	C8P—C7P—C6P	113.6 (19)
C3R—C2R—C1R	110.6 (6)	C7P—C8P—C3P	110.7 (16)
C8R—C3R—C2R	110.2 (8)	C7P—C9P—C1P	108.6 (13)
C8R—C3R—C4R	109.7 (7)	C19P—C10P—C1P	117.8 (15)
C2R—C3R—C4R	106.6 (7)	C19P—C10P—C5P	113.2 (10)
C5R—C4R—C3R	109.7 (6)	C1P—C10P—C5P	107.2 (13)
C4R—C5R—C10R	111.0 (6)	C19P—C10P—C11P	118.5 (19)
C4R—C5R—C6R	109.0 (7)	C1P—C10P—C11P	84.7 (7)
C10R—C5R—C6R	107.7 (6)	C5P—C10P—C11P	112.1 (14)
C7R—C6R—C5R	111.0 (6)	O1P—C11P—C12P	102.9 (13)
C8R—C7R—C9R	109.4 (9)	O1P—C11P—C2P	106.5 (14)
C8R—C7R—C6R	107.4 (7)	C12P—C11P—C2P	126.2 (7)
C9R—C7R—C6R	111.1 (7)	O1P—C11P—C10P	106.2 (15)
C7R—C8R—C3R	111.0 (7)	C12P—C11P—C10P	126.7 (8)
C7R—C9R—C1R	110.8 (6)	C2P—C11P—C10P	86.0 (6)
C11R—C10R—C5R	112.9 (5)	C13P—C12P—C17P	117.6 (4)
C11R—C10R—C19R	105.5 (6)	C13P—C12P—C11P	120.0 (5)
C5R—C10R—C19R	113.2 (8)	C17P—C12P—C11P	122.3 (5)
C11R—C10R—C1R	106.5 (6)	C12P—C13P—C14P	121.3 (5)
C5R—C10R—C1R	106.9 (5)	C13P—C14P—C15P	120.8 (5)
C19R—C10R—C1R	111.7 (6)	C14P—C15P—C16P	117.5 (5)
O1R—C11R—C12R	115.0 (5)	C14P—C15P—C18P	121.1 (6)
O1R—C11R—C10R	118.2 (5)	C16P—C15P—C18P	121.3 (6)
C12R—C11R—C10R	125.8 (5)	C17P—C16P—C15P	120.8 (5)
C13R—C12R—C17R	119.2 (4)	C16P—C17P—C12P	121.9 (5)
C13R—C12R—C11R	116.0 (4)	O2P—C18P—O3P	121.3 (14)
C17R—C12R—C11R	124.8 (5)	O2P—C18P—C15P	118.9 (12)
C14R—C13R—C12R	120.9 (4)	O3P—C18P—C15P	116.9 (13)
C13R—C14R—C15R	120.3 (4)	N1R—C20R—C22R	110.2 (6)
C16R—C15R—C14R	118.8 (4)	N1R—C20R—C21R	108.6 (7)
C16R—C15R—C18R	120.5 (4)	C22R—C20R—C21R	113.5 (8)
C14R—C15R—C18R	120.7 (4)	C27R—C22R—C23R	118.2 (5)
C15R—C16R—C17R	121.0 (3)	C27R—C22R—C20R	121.2 (7)
C12R—C17R—C16R	119.5 (4)	C23R—C22R—C20R	120.6 (6)
O2R—C18R—O3R	123.3 (7)	C22R—C23R—C24R	120.2 (5)
O2R—C18R—C15R	119.1 (7)	C25R—C24R—C23R	119.4 (6)
O3R—C18R—C15R	117.2 (6)	C24R—C25R—C26R	121.8 (6)
C9P—C1P—C2P	120.5 (11)	C25R—C26R—C27R	118.7 (6)
C9P—C1P—C10P	120.1 (11)	C22R—C27R—C26R	121.5 (6)
C2P—C1P—C10P	85.5 (7)	N1P—C20P—C22P	112.1 (10)
C3P—C2P—C11P	110.2 (12)	N1P—C20P—C21P	108.9 (10)
C3P—C2P—C1P	109.5 (12)	C22P—C20P—C21P	115.2 (9)
C11P—C2P—C1P	86.9 (7)	C27P—C22P—C23P	118.9 (7)
C2P—C3P—C4P	111.2 (13)	C27P—C22P—C20P	120.5 (8)
C2P—C3P—C8P	109.3 (16)	C23P—C22P—C20P	120.6 (8)
C4P—C3P—C8P	110.3 (18)	C24P—C23P—C22P	120.7 (7)
C3P—C4P—C5P	104.6 (14)	C25P—C24P—C23P	119.3 (8)
C4P—C5P—C6P	106.0 (9)	C26P—C25P—C24P	121.1 (8)
C4P—C5P—C10P	106.6 (15)	C25P—C26P—C27P	119.1 (8)
C6P—C5P—C10P	115.3 (17)	C22P—C27P—C26P	120.7 (8)
C5P—C6P—C7P	109.5 (15)

(42.3P)

Crystal data

C27H33NO3	Dx = 1.212 Mg m^−3
Mr = 419.54	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1628 reflections
a = 11.8971 (15) Å	θ = 6–19°
b = 29.579 (3) Å	µ = 0.08 mm^−1
c = 6.5350 (7) Å	T = 293 K
V = 2299.7 (4) Å^3	Block, colourless
Z = 4	0.56 × 0.41 × 0.20 mm
F(000) = 904

Data collection

Kuma KM4CCD diffractometer	2925 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.089
Graphite monochromator	θmax = 25.0°, θmin = 6.0°
ω scans	h = −14→13
10696 measured reflections	k = −35→35
3986 independent reflections	l = −6→7

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.085	w = 1/[σ^2(Fo^2) + (0.0901P)^2 + 1.1566P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.218	(Δ/σ)max = 0.002
S = 1.06	Δρmax = 0.18 e Å^−3
3986 reflections	Δρmin = −0.17 e Å^−3
561 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
310 restraints	Extinction coefficient: 0.094 (14)
Primary atom site location: structure-invariant direct methods	Absolute structure: The absolute configuration was assigned to agree with that from Leibovitch M. et all, 1997; 1998
Secondary atom site location: inferred from neighbouring sites

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1R	0.4134 (12)	0.2122 (4)	0.4755 (15)	0.101 (4)	0.577 (9)
C1R	0.4083 (12)	0.3039 (4)	0.5321 (16)	0.078 (6)	0.577 (9)
H1R	0.3595	0.2916	0.4248	0.094*	0.577 (9)
C2R	0.5269 (10)	0.3083 (3)	0.4504 (14)	0.100 (4)	0.577 (9)
H2AR	0.5541	0.2788	0.4083	0.120*	0.577 (9)
H2BR	0.5269	0.3279	0.3315	0.120*	0.577 (9)
C3R	0.6034 (10)	0.3274 (5)	0.6108 (18)	0.106 (5)	0.577 (9)
H3R	0.6795	0.3305	0.5553	0.127*	0.577 (9)
C4R	0.6047 (12)	0.2951 (5)	0.792 (2)	0.094 (5)	0.577 (9)
H4AR	0.6308	0.2656	0.7483	0.113*	0.577 (9)
H4BR	0.6556	0.3063	0.8963	0.113*	0.577 (9)
C5R	0.4881 (12)	0.2914 (5)	0.878 (2)	0.068 (4)	0.577 (9)
H5R	0.4890	0.2718	0.9992	0.082*	0.577 (9)
C6R	0.4409 (16)	0.3389 (4)	0.9365 (19)	0.104 (5)	0.577 (9)
H6AR	0.3647	0.3357	0.9872	0.125*	0.577 (9)
H6BR	0.4865	0.3518	1.0447	0.125*	0.577 (9)
C7R	0.4416 (11)	0.3699 (3)	0.753 (2)	0.092 (4)	0.577 (9)
H7R	0.4140	0.3999	0.7930	0.110*	0.577 (9)
C8R	0.5595 (11)	0.3736 (4)	0.678 (3)	0.123 (6)	0.577 (9)
H8AR	0.6071	0.3855	0.7858	0.148*	0.577 (9)
H8BR	0.5624	0.3944	0.5633	0.148*	0.577 (9)
C9R	0.3675 (13)	0.3505 (3)	0.592 (2)	0.097 (5)	0.577 (9)
H9AR	0.3678	0.3700	0.4726	0.116*	0.577 (9)
H9BR	0.2910	0.3486	0.6423	0.116*	0.577 (9)
C10R	0.4096 (11)	0.2713 (3)	0.7158 (18)	0.057 (3)	0.577 (9)
C11R	0.4466 (9)	0.2249 (3)	0.6476 (12)	0.060 (3)	0.577 (9)
C12R	0.5014 (8)	0.1888 (3)	0.7760 (15)	0.072 (5)	0.577 (9)
C13R	0.5783 (11)	0.1617 (4)	0.6755 (12)	0.065 (4)	0.577 (9)
H13R	0.5937	0.1670	0.5381	0.078*	0.577 (9)
C14R	0.6321 (14)	0.1272 (5)	0.7749 (16)	0.063 (5)	0.577 (9)
H14R	0.6826	0.1091	0.7036	0.076*	0.577 (9)
C15R	0.6125 (9)	0.1189 (3)	0.9796 (14)	0.043 (3)	0.577 (9)
C16R	0.5354 (11)	0.1461 (3)	1.0804 (13)	0.045 (3)	0.577 (9)
H16R	0.5180	0.1401	1.2165	0.054*	0.577 (9)
C17R	0.4838 (12)	0.1820 (4)	0.9824 (15)	0.057 (4)	0.577 (9)
H17R	0.4375	0.2015	1.0554	0.068*	0.577 (9)
C18R	0.6666 (11)	0.0789 (4)	1.082 (2)	0.060 (4)	0.577 (9)
C19R	0.2915 (15)	0.2652 (9)	0.797 (4)	0.122 (5)	0.577 (9)
H19A	0.2638	0.2936	0.8465	0.182*	0.577 (9)
H19B	0.2922	0.2436	0.9064	0.182*	0.577 (9)
H19C	0.2437	0.2544	0.6889	0.182*	0.577 (9)
O2R	0.6604 (16)	0.0758 (5)	1.2725 (15)	0.076 (4)	0.577 (9)
O3R	0.7038 (16)	0.0482 (5)	0.9656 (16)	0.073 (5)	0.577 (9)
O1P	0.3633 (16)	0.2122 (7)	0.521 (3)	0.138 (8)	0.423 (9)
HO1P	0.3971	0.1949	0.4449	0.206*	0.423 (9)
C1P	0.3958 (13)	0.2969 (5)	0.542 (3)	0.100 (10)	0.423 (9)
H1P	0.3385	0.2844	0.4498	0.120*	0.423 (9)
C2P	0.5032 (10)	0.2688 (3)	0.5247 (15)	0.089 (4)	0.423 (9)
H2P	0.5218	0.2583	0.3865	0.106*	0.423 (9)
C3P	0.5974 (11)	0.2908 (6)	0.639 (3)	0.099 (5)	0.423 (9)
H3P	0.6685	0.2767	0.5978	0.118*	0.423 (9)
C4P	0.5841 (15)	0.2867 (6)	0.866 (3)	0.077 (5)	0.423 (9)
H4AP	0.6363	0.3064	0.9368	0.092*	0.423 (9)
H4BP	0.5961	0.2558	0.9102	0.092*	0.423 (9)
C5P	0.4629 (15)	0.3013 (6)	0.903 (3)	0.085 (9)	0.423 (9)
H5P	0.4424	0.2945	1.0448	0.102*	0.423 (9)
C6P	0.461 (2)	0.3534 (5)	0.871 (3)	0.141 (10)	0.423 (9)
H6AP	0.3866	0.3650	0.9002	0.169*	0.423 (9)
H6BP	0.5138	0.3677	0.9636	0.169*	0.423 (9)
C7P	0.4930 (17)	0.3642 (5)	0.649 (3)	0.120 (8)	0.423 (9)
H7P	0.5017	0.3970	0.6320	0.144*	0.423 (9)
C8P	0.5981 (16)	0.3399 (8)	0.573 (4)	0.151 (9)	0.423 (9)
H8AP	0.6013	0.3416	0.4248	0.181*	0.423 (9)
H8BP	0.6644	0.3547	0.6274	0.181*	0.423 (9)
C9P	0.4002 (15)	0.3475 (4)	0.517 (3)	0.109 (9)	0.423 (9)
H9AP	0.4141	0.3554	0.3757	0.131*	0.423 (9)
H9BP	0.3294	0.3609	0.5592	0.131*	0.423 (9)
C10P	0.3824 (13)	0.2757 (4)	0.757 (2)	0.078 (6)	0.423 (9)
C11P	0.4437 (11)	0.2348 (3)	0.6577 (19)	0.094 (8)	0.423 (9)
C12P	0.4967 (9)	0.1955 (3)	0.7671 (15)	0.046 (4)	0.423 (9)
C13P	0.5845 (11)	0.1723 (5)	0.6807 (18)	0.053 (5)	0.423 (9)
H13P	0.6125	0.1817	0.5548	0.064*	0.423 (9)
C14P	0.6323 (15)	0.1353 (6)	0.777 (2)	0.050 (5)	0.423 (9)
H14P	0.6918	0.1202	0.7146	0.060*	0.423 (9)
C15P	0.5921 (13)	0.1204 (5)	0.9646 (19)	0.046 (4)	0.423 (9)
C16P	0.5066 (14)	0.1456 (5)	1.0562 (18)	0.068 (7)	0.423 (9)
H16P	0.4805	0.1374	1.1851	0.081*	0.423 (9)
C17P	0.4609 (17)	0.1820 (6)	0.959 (2)	0.059 (5)	0.423 (9)
H17P	0.4042	0.1983	1.0241	0.071*	0.423 (9)
C18P	0.6432 (13)	0.0811 (4)	1.0704 (14)	0.035 (3)	0.423 (9)
C19P	0.2674 (18)	0.2701 (13)	0.839 (5)	0.136 (8)	0.423 (9)
H19D	0.2712	0.2564	0.9721	0.204*	0.423 (9)
H19E	0.2245	0.2512	0.7491	0.204*	0.423 (9)
H19F	0.2320	0.2992	0.8499	0.204*	0.423 (9)
O2P	0.646 (2)	0.0815 (7)	1.2624 (14)	0.081 (6)	0.423 (9)
O3P	0.6960 (18)	0.0524 (6)	0.965 (3)	0.075 (7)	0.423 (9)
N1R	0.6489 (16)	0.0172 (8)	0.557 (3)	0.061 (5)	0.577 (9)
H1NR	0.7015	0.0000	0.4987	0.092*	0.577 (9)
H2NR	0.6721	0.0260	0.6798	0.092*	0.577 (9)
H3NR	0.6364	0.0414	0.4788	0.092*	0.577 (9)
C20R	0.5430 (12)	−0.0093 (6)	0.577 (2)	0.072 (10)	0.577 (9)
H20R	0.5548	−0.0352	0.6681	0.086*	0.577 (9)
C21R	0.5155 (19)	−0.0256 (6)	0.359 (3)	0.091 (6)	0.577 (9)
H21A	0.5762	−0.0440	0.3091	0.137*	0.577 (9)
H21B	0.5057	0.0000	0.2708	0.137*	0.577 (9)
H21C	0.4476	−0.0432	0.3615	0.137*	0.577 (9)
C22R	0.4544 (10)	0.0214 (4)	0.6636 (18)	0.070 (6)	0.577 (9)
C23R	0.4256 (13)	0.0617 (5)	0.570 (2)	0.076 (4)	0.577 (9)
H23R	0.4611	0.0702	0.4491	0.091*	0.577 (9)
C24R	0.3431 (11)	0.0896 (4)	0.656 (2)	0.093 (4)	0.577 (9)
H24R	0.3238	0.1168	0.5931	0.112*	0.577 (9)
C25R	0.2930 (11)	0.0769 (5)	0.828 (2)	0.095 (5)	0.577 (9)
H25R	0.2393	0.0958	0.8858	0.114*	0.577 (9)
C26R	0.3173 (15)	0.0371 (6)	0.923 (2)	0.104 (5)	0.577 (9)
H26R	0.2782	0.0284	1.0396	0.125*	0.577 (9)
C27R	0.4001 (17)	0.0101 (6)	0.844 (3)	0.084 (4)	0.577 (9)
H27R	0.4203	−0.0162	0.9121	0.101*	0.577 (9)
N1P	0.6562 (17)	0.0129 (10)	0.595 (4)	0.043 (4)	0.423 (9)
H1NP	0.7075	−0.0074	0.5587	0.064*	0.423 (9)
H2NP	0.6694	0.0220	0.7226	0.064*	0.423 (9)
H3NP	0.6598	0.0365	0.5108	0.064*	0.423 (9)
C20P	0.5433 (16)	−0.0075 (6)	0.583 (4)	0.073 (15)	0.423 (9)
H20P	0.5422	−0.0311	0.6889	0.088*	0.423 (9)
C21P	0.531 (3)	−0.0324 (10)	0.381 (5)	0.106 (10)	0.423 (9)
H21D	0.5957	−0.0514	0.3599	0.159*	0.423 (9)
H21E	0.5261	−0.0109	0.2715	0.159*	0.423 (9)
H21F	0.4646	−0.0507	0.3837	0.159*	0.423 (9)
C22P	0.4487 (11)	0.0236 (6)	0.635 (3)	0.074 (9)	0.423 (9)
C23P	0.4136 (19)	0.0563 (8)	0.496 (3)	0.099 (9)	0.423 (9)
H23P	0.4484	0.0584	0.3694	0.118*	0.423 (9)
C24P	0.3279 (15)	0.0856 (7)	0.545 (3)	0.117 (8)	0.423 (9)
H24P	0.3061	0.1079	0.4531	0.140*	0.423 (9)
C25P	0.2750 (16)	0.0815 (9)	0.731 (3)	0.120 (9)	0.423 (9)
H25P	0.2154	0.1006	0.7620	0.144*	0.423 (9)
C26P	0.308 (3)	0.0501 (12)	0.870 (4)	0.148 (14)	0.423 (9)
H26P	0.2732	0.0484	0.9967	0.178*	0.423 (9)
C27P	0.395 (3)	0.0202 (11)	0.819 (4)	0.126 (10)	0.423 (9)
H27P	0.4160	−0.0021	0.9116	0.151*	0.423 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1R	0.148 (11)	0.063 (4)	0.091 (5)	0.034 (6)	−0.055 (7)	−0.024 (4)
C1R	0.130 (15)	0.049 (6)	0.056 (7)	0.008 (7)	−0.027 (8)	−0.005 (5)
C2R	0.149 (10)	0.081 (6)	0.071 (6)	0.018 (7)	0.011 (7)	0.022 (5)
C3R	0.071 (7)	0.118 (14)	0.128 (10)	0.001 (7)	0.025 (7)	0.032 (10)
C4R	0.105 (10)	0.080 (8)	0.098 (11)	−0.013 (7)	−0.042 (8)	0.036 (8)
C5R	0.112 (12)	0.042 (4)	0.051 (5)	0.024 (7)	−0.009 (6)	−0.003 (4)
C6R	0.189 (13)	0.051 (7)	0.073 (7)	0.020 (8)	0.002 (7)	−0.019 (6)
C7R	0.124 (10)	0.041 (5)	0.110 (10)	0.010 (6)	−0.017 (7)	−0.003 (6)
C8R	0.127 (11)	0.068 (7)	0.174 (13)	−0.016 (8)	−0.036 (10)	0.046 (8)
C9R	0.118 (9)	0.048 (5)	0.125 (12)	0.017 (5)	−0.033 (9)	0.005 (6)
C10R	0.060 (6)	0.038 (4)	0.074 (6)	0.019 (4)	0.003 (5)	−0.002 (4)
C11R	0.086 (8)	0.037 (4)	0.057 (6)	0.011 (4)	0.005 (5)	−0.002 (4)
C12R	0.074 (10)	0.065 (7)	0.076 (10)	0.017 (7)	−0.020 (8)	0.017 (6)
C13R	0.110 (9)	0.036 (5)	0.048 (5)	0.004 (5)	0.023 (6)	−0.006 (4)
C14R	0.095 (10)	0.030 (5)	0.064 (9)	0.014 (5)	0.002 (7)	0.001 (4)
C15R	0.042 (4)	0.045 (4)	0.041 (4)	0.005 (3)	0.004 (3)	−0.003 (3)
C16R	0.063 (7)	0.028 (4)	0.044 (4)	0.004 (3)	−0.004 (4)	0.004 (3)
C17R	0.060 (7)	0.040 (6)	0.071 (7)	0.016 (4)	0.000 (5)	0.006 (5)
C18R	0.038 (5)	0.047 (6)	0.096 (9)	0.002 (4)	−0.016 (5)	0.030 (6)
C19R	0.087 (9)	0.096 (8)	0.182 (13)	0.019 (8)	0.034 (9)	−0.005 (9)
O2R	0.105 (8)	0.054 (5)	0.069 (7)	0.002 (5)	−0.012 (5)	0.018 (4)
O3R	0.117 (10)	0.053 (6)	0.048 (6)	0.041 (6)	−0.003 (6)	−0.001 (5)
O1P	0.135 (15)	0.113 (10)	0.165 (13)	0.002 (10)	−0.061 (11)	−0.024 (9)
C1P	0.109 (18)	0.064 (12)	0.13 (2)	0.014 (11)	−0.034 (14)	0.025 (12)
C2P	0.142 (12)	0.063 (7)	0.061 (6)	0.032 (8)	0.000 (7)	0.017 (5)
C3P	0.076 (9)	0.088 (12)	0.132 (14)	0.011 (8)	0.005 (10)	0.047 (11)
C4P	0.073 (10)	0.072 (10)	0.085 (11)	−0.003 (7)	−0.031 (8)	0.002 (8)
C5P	0.090 (11)	0.10 (2)	0.067 (9)	0.032 (10)	0.005 (8)	−0.002 (10)
C6P	0.25 (2)	0.056 (13)	0.12 (2)	0.020 (15)	0.008 (18)	−0.001 (11)
C7P	0.14 (2)	0.052 (9)	0.16 (2)	0.026 (11)	0.025 (17)	0.013 (11)
C8P	0.146 (17)	0.119 (15)	0.189 (19)	−0.018 (14)	−0.011 (15)	0.056 (15)
C9P	0.135 (15)	0.104 (14)	0.089 (11)	0.015 (11)	0.001 (10)	0.024 (9)
C10P	0.052 (10)	0.097 (12)	0.087 (10)	0.009 (7)	0.016 (7)	−0.015 (8)
C11P	0.071 (10)	0.090 (12)	0.120 (14)	0.025 (9)	−0.040 (9)	0.009 (10)
C12P	0.070 (10)	0.028 (5)	0.040 (8)	0.001 (6)	0.010 (7)	−0.001 (5)
C13P	0.061 (7)	0.034 (6)	0.065 (8)	0.000 (5)	−0.002 (6)	0.025 (5)
C14P	0.064 (10)	0.039 (8)	0.046 (9)	0.011 (6)	0.025 (7)	0.002 (5)
C15P	0.047 (6)	0.046 (5)	0.046 (6)	0.008 (4)	−0.009 (4)	0.010 (4)
C16P	0.046 (8)	0.112 (15)	0.045 (7)	−0.003 (7)	0.014 (6)	−0.005 (7)
C17P	0.054 (8)	0.060 (9)	0.063 (9)	0.017 (6)	0.005 (7)	−0.006 (7)
C18P	0.038 (5)	0.037 (5)	0.029 (4)	0.006 (3)	0.005 (3)	−0.011 (4)
C19P	0.088 (12)	0.126 (15)	0.194 (17)	0.021 (12)	0.038 (12)	0.012 (14)
O2P	0.133 (12)	0.072 (8)	0.038 (7)	0.047 (7)	0.010 (7)	0.016 (5)
O3P	0.063 (9)	0.056 (10)	0.107 (15)	0.018 (8)	0.005 (8)	−0.010 (9)
N1R	0.079 (7)	0.051 (5)	0.053 (10)	0.020 (5)	−0.010 (5)	0.011 (6)
C20R	0.08 (2)	0.077 (15)	0.060 (13)	0.010 (12)	−0.005 (12)	0.009 (10)
C21R	0.124 (14)	0.060 (7)	0.089 (10)	−0.001 (8)	−0.012 (8)	−0.032 (8)
C22R	0.081 (12)	0.064 (11)	0.066 (7)	0.003 (8)	−0.008 (7)	0.008 (7)
C23R	0.067 (7)	0.076 (8)	0.084 (8)	0.001 (6)	0.010 (6)	0.020 (6)
C24R	0.059 (7)	0.071 (6)	0.150 (13)	0.017 (6)	−0.021 (9)	0.003 (7)
C25R	0.064 (10)	0.125 (13)	0.094 (11)	0.011 (9)	0.007 (8)	−0.002 (10)
C26R	0.078 (9)	0.153 (15)	0.081 (8)	0.002 (9)	0.022 (7)	0.011 (9)
C27R	0.075 (8)	0.099 (8)	0.079 (7)	0.007 (6)	0.017 (6)	0.017 (6)
N1P	0.048 (6)	0.055 (8)	0.024 (5)	0.012 (5)	−0.003 (4)	0.010 (5)
C20P	0.09 (3)	0.029 (11)	0.10 (3)	−0.005 (13)	0.018 (19)	0.007 (12)
C21P	0.077 (11)	0.103 (17)	0.14 (2)	−0.007 (10)	−0.043 (11)	0.054 (14)
C22P	0.039 (10)	0.08 (2)	0.101 (14)	−0.008 (10)	0.015 (9)	0.009 (12)
C23P	0.086 (13)	0.080 (12)	0.130 (19)	0.016 (10)	0.012 (14)	0.023 (13)
C24P	0.065 (12)	0.121 (15)	0.17 (2)	0.001 (10)	0.003 (13)	−0.014 (15)
C25P	0.056 (9)	0.152 (18)	0.15 (2)	0.042 (11)	−0.028 (15)	−0.019 (19)
C26P	0.100 (17)	0.20 (3)	0.14 (2)	0.04 (2)	0.016 (15)	0.09 (2)
C27P	0.12 (2)	0.13 (2)	0.123 (19)	−0.010 (16)	−0.037 (16)	0.011 (15)

Geometric parameters (Å, º)

O1R—C11R	1.250 (8)	C5P—C6P	1.555 (10)
C1R—C9R	1.513 (13)	C6P—C7P	1.532 (16)
C1R—C2R	1.514 (14)	C7P—C9P	1.485 (10)
C1R—C10R	1.540 (12)	C7P—C8P	1.527 (16)
C2R—C3R	1.499 (9)	C10P—C19P	1.480 (13)
C3R—C4R	1.521 (10)	C10P—C11P	1.553 (5)
C3R—C8R	1.527 (15)	C11P—C12P	1.503 (6)
C4R—C5R	1.501 (9)	C12P—C13P	1.371 (7)
C5R—C10R	1.533 (12)	C12P—C17P	1.385 (7)
C5R—C6R	1.560 (13)	C13P—C14P	1.385 (7)
C6R—C7R	1.510 (14)	C14P—C15P	1.389 (7)
C7R—C9R	1.491 (9)	C15P—C16P	1.396 (7)
C7R—C8R	1.491 (14)	C15P—C18P	1.483 (7)
C10R—C11R	1.508 (8)	C16P—C17P	1.363 (7)
C10R—C19R	1.512 (13)	C18P—O2P	1.256 (5)
C11R—C12R	1.507 (4)	C18P—O3P	1.261 (8)
C12R—C17R	1.379 (7)	N1R—C20R	1.489 (14)
C12R—C13R	1.382 (9)	C20R—C22R	1.502 (9)
C13R—C14R	1.368 (8)	C20R—C21R	1.540 (9)
C14R—C15R	1.380 (7)	C22R—C23R	1.381 (8)
C15R—C16R	1.386 (7)	C22R—C27R	1.383 (8)
C15R—C18R	1.505 (8)	C23R—C24R	1.401 (8)
C16R—C17R	1.384 (7)	C24R—C25R	1.328 (9)
C18R—O2R	1.249 (10)	C25R—C26R	1.360 (9)
C18R—O3R	1.268 (11)	C26R—C27R	1.370 (8)
O1P—C11P	1.469 (15)	N1P—C20P	1.475 (16)
C1P—C9P	1.507 (10)	C20P—C22P	1.494 (10)
C1P—C2P	1.528 (10)	C20P—C21P	1.520 (16)
C1P—C10P	1.547 (10)	C22P—C27P	1.366 (8)
C2P—C3P	1.495 (15)	C22P—C23P	1.390 (8)
C2P—C11P	1.505 (8)	C23P—C24P	1.375 (8)
C3P—C4P	1.497 (10)	C24P—C25P	1.373 (9)
C3P—C8P	1.514 (17)	C25P—C26P	1.356 (9)
C4P—C5P	1.524 (10)	C26P—C27P	1.399 (9)
C5P—C10P	1.551 (10)
C9R—C1R—C2R	108.1 (12)	C9P—C7P—C8P	105.2 (12)
C9R—C1R—C10R	111.9 (9)	C9P—C7P—C6P	107.1 (16)
C2R—C1R—C10R	108.6 (9)	C8P—C7P—C6P	114.4 (11)
C3R—C2R—C1R	110.6 (8)	C3P—C8P—C7P	110.8 (12)
C2R—C3R—C4R	108.3 (10)	C7P—C9P—C1P	107.2 (11)
C2R—C3R—C8R	109.3 (11)	C19P—C10P—C1P	118.1 (14)
C4R—C3R—C8R	110.0 (10)	C19P—C10P—C5P	113.6 (10)
C5R—C4R—C3R	109.2 (9)	C1P—C10P—C5P	107.3 (12)
C4R—C5R—C10R	109.4 (11)	C19P—C10P—C11P	120.0 (16)
C4R—C5R—C6R	110.9 (11)	C1P—C10P—C11P	83.6 (6)
C10R—C5R—C6R	107.4 (10)	C5P—C10P—C11P	110.3 (11)
C7R—C6R—C5R	110.6 (10)	O1P—C11P—C12P	102.2 (10)
C9R—C7R—C8R	110.5 (12)	O1P—C11P—C2P	105.0 (12)
C9R—C7R—C6R	108.9 (11)	C12P—C11P—C2P	126.4 (6)
C8R—C7R—C6R	108.1 (11)	O1P—C11P—C10P	107.5 (12)
C7R—C8R—C3R	110.6 (10)	C12P—C11P—C10P	126.9 (6)
C7R—C9R—C1R	110.2 (9)	C2P—C11P—C10P	86.7 (5)
C11R—C10R—C19R	105.4 (11)	C13P—C12P—C17P	117.6 (4)
C11R—C10R—C5R	112.2 (9)	C13P—C12P—C11P	120.7 (5)
C19R—C10R—C5R	111.7 (11)	C17P—C12P—C11P	121.6 (6)
C11R—C10R—C1R	110.0 (8)	C12P—C13P—C14P	121.5 (5)
C19R—C10R—C1R	109.8 (12)	C13P—C14P—C15P	120.6 (5)
C5R—C10R—C1R	107.6 (9)	C14P—C15P—C16P	117.5 (4)
O1R—C11R—C12R	115.1 (6)	C14P—C15P—C18P	121.3 (6)
O1R—C11R—C10R	116.6 (7)	C16P—C15P—C18P	121.1 (5)
C12R—C11R—C10R	127.4 (6)	C17P—C16P—C15P	120.9 (5)
C17R—C12R—C13R	118.7 (4)	C16P—C17P—C12P	121.7 (5)
C17R—C12R—C11R	125.6 (7)	O2P—C18P—O3P	122.6 (11)
C13R—C12R—C11R	115.6 (6)	O2P—C18P—C15P	118.1 (8)
C14R—C13R—C12R	121.0 (5)	O3P—C18P—C15P	118.4 (8)
C13R—C14R—C15R	120.9 (5)	N1R—C20R—C22R	108.1 (12)
C14R—C15R—C16R	118.0 (5)	N1R—C20R—C21R	105.1 (13)
C14R—C15R—C18R	120.0 (7)	C22R—C20R—C21R	112.9 (10)
C16R—C15R—C18R	121.8 (6)	C23R—C22R—C27R	118.1 (6)
C17R—C16R—C15R	121.2 (4)	C23R—C22R—C20R	121.8 (7)
C12R—C17R—C16R	119.8 (5)	C27R—C22R—C20R	120.1 (7)
O2R—C18R—O3R	124.5 (9)	C22R—C23R—C24R	120.3 (7)
O2R—C18R—C15R	118.5 (9)	C25R—C24R—C23R	119.1 (7)
O3R—C18R—C15R	116.4 (9)	C24R—C25R—C26R	122.4 (7)
C9P—C1P—C2P	120.3 (10)	C25R—C26R—C27R	119.0 (7)
C9P—C1P—C10P	120.1 (10)	C26R—C27R—C22R	121.0 (7)
C2P—C1P—C10P	86.1 (6)	N1P—C20P—C22P	114.9 (14)
C3P—C2P—C11P	110.9 (10)	N1P—C20P—C21P	109.2 (17)
C3P—C2P—C1P	110.7 (10)	C22P—C20P—C21P	115.2 (15)
C11P—C2P—C1P	85.9 (7)	C27P—C22P—C23P	119.0 (7)
C2P—C3P—C4P	112.2 (12)	C27P—C22P—C20P	120.5 (8)
C2P—C3P—C8P	106.4 (14)	C23P—C22P—C20P	120.5 (8)
C4P—C3P—C8P	111.1 (16)	C24P—C23P—C22P	120.7 (7)
C3P—C4P—C5P	103.6 (12)	C25P—C24P—C23P	119.2 (8)
C4P—C5P—C10P	110.3 (13)	C26P—C25P—C24P	121.3 (7)
C4P—C5P—C6P	105.8 (9)	C25P—C26P—C27P	119.3 (8)
C10P—C5P—C6P	113.1 (14)	C22P—C27P—C26P	120.4 (8)
C7P—C6P—C5P	109.4 (12)

(51.8P)

Crystal data

C27H33NO3	Dx = 1.210 Mg m^−3
Mr = 419.54	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1447 reflections
a = 11.9628 (18) Å	θ = 6–19°
b = 29.503 (4) Å	µ = 0.08 mm^−1
c = 6.5269 (8) Å	T = 293 K
V = 2303.6 (5) Å^3	Block, colourless
Z = 4	0.56 × 0.41 × 0.20 mm
F(000) = 904

Data collection

Kuma KM4CCD diffractometer	2853 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.104
Graphite monochromator	θmax = 25.0°, θmin = 6.0°
ω scans	h = −13→14
10634 measured reflections	k = −35→34
3991 independent reflections	l = −7→6

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.098	w = 1/[σ^2(Fo^2) + (0.106P)^2 + 1.3608P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.256	(Δ/σ)max = 0.001
S = 1.08	Δρmax = 0.19 e Å^−3
3991 reflections	Δρmin = −0.18 e Å^−3
561 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
340 restraints	Extinction coefficient: 0.130 (19)
Primary atom site location: structure-invariant direct methods	Absolute structure: The absolute configuration was assigned to agree with that from Leibovitch M. et all, 1997; 1998
Secondary atom site location: inferred from neighbouring sites

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1R	0.4117 (18)	0.2131 (7)	0.480 (3)	0.120 (7)	0.482 (10)
C1R	0.4068 (16)	0.3043 (6)	0.536 (3)	0.090 (8)	0.482 (10)
H1R	0.3568	0.2920	0.4305	0.108*	0.482 (10)
C2R	0.5234 (15)	0.3086 (5)	0.448 (2)	0.113 (6)	0.482 (10)
H2AR	0.5512	0.2789	0.4091	0.136*	0.482 (10)
H2BR	0.5215	0.3275	0.3258	0.136*	0.482 (10)
C3R	0.5999 (15)	0.3296 (6)	0.605 (3)	0.127 (9)	0.482 (10)
H3R	0.6748	0.3336	0.5471	0.153*	0.482 (10)
C4R	0.6044 (14)	0.2956 (7)	0.782 (3)	0.094 (7)	0.482 (10)
H4AR	0.6280	0.2662	0.7307	0.113*	0.482 (10)
H4BR	0.6583	0.3056	0.8831	0.113*	0.482 (10)
C5R	0.4910 (16)	0.2916 (6)	0.878 (3)	0.080 (6)	0.482 (10)
H5R	0.4950	0.2718	0.9987	0.096*	0.482 (10)
C6R	0.446 (3)	0.3388 (6)	0.942 (3)	0.146 (9)	0.482 (10)
H6AR	0.3720	0.3354	1.0011	0.176*	0.482 (10)
H6BR	0.4945	0.3518	1.0449	0.176*	0.482 (10)
C7R	0.4397 (13)	0.3700 (4)	0.761 (3)	0.103 (5)	0.482 (10)
H7R	0.4112	0.3996	0.8046	0.123*	0.482 (10)
C8R	0.5555 (15)	0.3749 (6)	0.680 (3)	0.132 (7)	0.482 (10)
H8AR	0.6040	0.3866	0.7868	0.158*	0.482 (10)
H8BR	0.5557	0.3964	0.5676	0.158*	0.482 (10)
C9R	0.3667 (17)	0.3511 (5)	0.596 (3)	0.115 (8)	0.482 (10)
H9AR	0.3684	0.3710	0.4779	0.138*	0.482 (10)
H9BR	0.2902	0.3493	0.6448	0.138*	0.482 (10)
C10R	0.4096 (14)	0.2715 (4)	0.720 (2)	0.064 (4)	0.482 (10)
C11R	0.4492 (14)	0.2258 (4)	0.6470 (17)	0.069 (5)	0.482 (10)
C12R	0.5069 (10)	0.1898 (3)	0.7714 (17)	0.059 (5)	0.482 (10)
C13R	0.5809 (17)	0.1626 (5)	0.6683 (17)	0.082 (7)	0.482 (10)
H13R	0.5947	0.1678	0.5301	0.099*	0.482 (10)
C14R	0.6348 (17)	0.1276 (6)	0.767 (2)	0.053 (4)	0.482 (10)
H14R	0.6840	0.1092	0.6942	0.063*	0.482 (10)
C15R	0.6165 (12)	0.1196 (4)	0.972 (2)	0.048 (4)	0.482 (10)
C16R	0.5423 (10)	0.1469 (4)	1.0755 (15)	0.040 (3)	0.482 (10)
H16R	0.5259	0.1408	1.2120	0.047*	0.482 (10)
C17R	0.4914 (10)	0.1837 (4)	0.9788 (16)	0.049 (4)	0.482 (10)
H17R	0.4475	0.2038	1.0533	0.059*	0.482 (10)
C18R	0.6679 (16)	0.0786 (5)	1.069 (3)	0.048 (4)	0.482 (10)
C19R	0.2936 (18)	0.2654 (11)	0.810 (5)	0.126 (6)	0.482 (10)
H19A	0.2666	0.2940	0.8596	0.189*	0.482 (10)
H19B	0.2970	0.2442	0.9217	0.189*	0.482 (10)
H19C	0.2440	0.2541	0.7067	0.189*	0.482 (10)
O2R	0.669 (3)	0.0759 (10)	1.260 (2)	0.077 (6)	0.482 (10)
O3R	0.6945 (15)	0.0452 (6)	0.952 (2)	0.052 (3)	0.482 (10)
O1P	0.3617 (15)	0.2104 (8)	0.520 (3)	0.132 (8)	0.518 (10)
HO1P	0.3973	0.1933	0.4453	0.198*	0.518 (10)
C1P	0.3934 (12)	0.2965 (5)	0.537 (2)	0.078 (6)	0.518 (10)
H1P	0.3363	0.2841	0.4455	0.094*	0.518 (10)
C2P	0.4997 (10)	0.2679 (3)	0.5240 (14)	0.094 (4)	0.518 (10)
H2P	0.5163	0.2567	0.3861	0.113*	0.518 (10)
C3P	0.5960 (11)	0.2918 (5)	0.626 (3)	0.104 (5)	0.518 (10)
H3P	0.6664	0.2778	0.5820	0.125*	0.518 (10)
C4P	0.5836 (13)	0.2868 (6)	0.854 (2)	0.087 (5)	0.518 (10)
H4AP	0.6360	0.3062	0.9262	0.105*	0.518 (10)
H4BP	0.5960	0.2556	0.8963	0.105*	0.518 (10)
C5P	0.4631 (14)	0.3012 (5)	0.897 (3)	0.089 (7)	0.518 (10)
H5P	0.4450	0.2938	1.0394	0.107*	0.518 (10)
C6P	0.461 (2)	0.3535 (5)	0.872 (3)	0.146 (9)	0.518 (10)
H6AP	0.3879	0.3653	0.9059	0.175*	0.518 (10)
H6BP	0.5156	0.3673	0.9631	0.175*	0.518 (10)
C7P	0.4903 (14)	0.3648 (4)	0.646 (3)	0.118 (6)	0.518 (10)
H7P	0.4974	0.3977	0.6294	0.141*	0.518 (10)
C8P	0.5954 (14)	0.3412 (7)	0.565 (4)	0.144 (9)	0.518 (10)
H8AP	0.5977	0.3437	0.4170	0.173*	0.518 (10)
H8BP	0.6613	0.3561	0.6199	0.173*	0.518 (10)
C9P	0.3992 (13)	0.3473 (4)	0.513 (2)	0.112 (7)	0.518 (10)
H9AP	0.4142	0.3550	0.3710	0.134*	0.518 (10)
H9BP	0.3285	0.3609	0.5519	0.134*	0.518 (10)
C10P	0.3799 (12)	0.2757 (4)	0.754 (2)	0.079 (5)	0.518 (10)
C11P	0.4387 (10)	0.2343 (4)	0.658 (2)	0.087 (7)	0.518 (10)
C12P	0.4911 (9)	0.1949 (3)	0.7703 (16)	0.068 (5)	0.518 (10)
C13P	0.5782 (10)	0.1716 (5)	0.6810 (15)	0.057 (4)	0.518 (10)
H13P	0.6048	0.1810	0.5540	0.069*	0.518 (10)
C14P	0.6268 (16)	0.1348 (6)	0.775 (2)	0.067 (6)	0.518 (10)
H14P	0.6846	0.1195	0.7094	0.080*	0.518 (10)
C15P	0.5911 (10)	0.1200 (4)	0.967 (2)	0.045 (3)	0.518 (10)
C16P	0.5036 (9)	0.1440 (4)	1.0575 (16)	0.057 (4)	0.518 (10)
H16P	0.4775	0.1353	1.1857	0.068*	0.518 (10)
C17P	0.4557 (9)	0.1801 (4)	0.9611 (17)	0.053 (4)	0.518 (10)
H17P	0.3974	0.1952	1.0254	0.064*	0.518 (10)
C18P	0.6433 (13)	0.0813 (5)	1.073 (2)	0.047 (4)	0.518 (10)
C19P	0.2666 (15)	0.2715 (10)	0.843 (4)	0.131 (7)	0.518 (10)
H19D	0.2713	0.2577	0.9756	0.197*	0.518 (10)
H19E	0.2212	0.2530	0.7547	0.197*	0.518 (10)
H19F	0.2336	0.3011	0.8550	0.197*	0.518 (10)
O2P	0.641 (3)	0.0800 (9)	1.265 (2)	0.071 (6)	0.518 (10)
O3P	0.7070 (17)	0.0552 (6)	0.971 (3)	0.080 (6)	0.518 (10)
N1R	0.6523 (17)	0.0173 (9)	0.549 (4)	0.056 (5)	0.482 (10)
H1NR	0.7057	0.0006	0.4914	0.084*	0.482 (10)
H2NR	0.6738	0.0256	0.6741	0.084*	0.482 (10)
H3NR	0.6401	0.0419	0.4732	0.084*	0.482 (10)
C20R	0.5481 (14)	−0.0096 (6)	0.563 (3)	0.074 (10)	0.482 (10)
H20R	0.5618	−0.0354	0.6544	0.089*	0.482 (10)
C21R	0.519 (2)	−0.0282 (8)	0.351 (4)	0.095 (9)	0.482 (10)
H21A	0.5796	−0.0464	0.3013	0.143*	0.482 (10)
H21B	0.5065	−0.0034	0.2582	0.143*	0.482 (10)
H21C	0.4525	−0.0463	0.3596	0.143*	0.482 (10)
C22R	0.4578 (11)	0.0194 (6)	0.658 (2)	0.084 (8)	0.482 (10)
C23R	0.4246 (16)	0.0590 (7)	0.566 (3)	0.091 (7)	0.482 (10)
H23R	0.4578	0.0679	0.4431	0.109*	0.482 (10)
C24R	0.342 (2)	0.0863 (7)	0.654 (4)	0.107 (7)	0.482 (10)
H24R	0.3193	0.1131	0.5905	0.128*	0.482 (10)
C25R	0.2952 (15)	0.0732 (6)	0.829 (3)	0.089 (6)	0.482 (10)
H25R	0.2424	0.0919	0.8906	0.106*	0.482 (10)
C26R	0.3224 (18)	0.0334 (8)	0.922 (3)	0.102 (7)	0.482 (10)
H26R	0.2850	0.0240	1.0390	0.123*	0.482 (10)
C27R	0.4057 (18)	0.0073 (7)	0.839 (3)	0.082 (5)	0.482 (10)
H27R	0.4277	−0.0190	0.9065	0.099*	0.482 (10)
N1P	0.6530 (16)	0.0128 (8)	0.587 (3)	0.053 (4)	0.518 (10)
H1NP	0.7044	−0.0075	0.5507	0.079*	0.518 (10)
H2NP	0.6676	0.0228	0.7127	0.079*	0.518 (10)
H3NP	0.6541	0.0359	0.4994	0.079*	0.518 (10)
C20P	0.5411 (12)	−0.0087 (5)	0.584 (3)	0.072 (9)	0.518 (10)
H20P	0.5420	−0.0329	0.6869	0.086*	0.518 (10)
C21P	0.529 (2)	−0.0313 (8)	0.377 (4)	0.120 (12)	0.518 (10)
H21D	0.5925	−0.0504	0.3521	0.180*	0.518 (10)
H21E	0.5251	−0.0085	0.2720	0.180*	0.518 (10)
H21F	0.4621	−0.0491	0.3747	0.180*	0.518 (10)
C22P	0.4490 (8)	0.0227 (4)	0.640 (2)	0.069 (7)	0.518 (10)
C23P	0.419 (2)	0.0574 (6)	0.509 (3)	0.117 (10)	0.518 (10)
H23P	0.4562	0.0608	0.3851	0.140*	0.518 (10)
C24P	0.334 (2)	0.0869 (8)	0.559 (4)	0.136 (12)	0.518 (10)
H24P	0.3140	0.1102	0.4702	0.163*	0.518 (10)
C25P	0.2792 (17)	0.0813 (8)	0.742 (3)	0.120 (8)	0.518 (10)
H25P	0.2222	0.1013	0.7776	0.144*	0.518 (10)
C26P	0.3064 (18)	0.0474 (9)	0.873 (3)	0.127 (10)	0.518 (10)
H26P	0.2685	0.0441	0.9969	0.152*	0.518 (10)
C27P	0.392 (2)	0.0173 (8)	0.820 (3)	0.109 (8)	0.518 (10)
H27P	0.4106	−0.0065	0.9074	0.131*	0.518 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1R	0.155 (17)	0.077 (7)	0.127 (9)	0.029 (10)	−0.075 (11)	−0.032 (7)
C1R	0.114 (17)	0.042 (7)	0.114 (18)	0.011 (9)	−0.034 (14)	−0.007 (8)
C2R	0.165 (17)	0.090 (10)	0.084 (8)	0.026 (10)	0.006 (10)	0.003 (8)
C3R	0.111 (16)	0.13 (2)	0.144 (18)	0.020 (13)	0.055 (14)	0.031 (15)
C4R	0.085 (10)	0.075 (10)	0.123 (19)	−0.016 (8)	−0.020 (12)	0.030 (12)
C5R	0.128 (15)	0.049 (7)	0.063 (8)	0.029 (9)	−0.015 (9)	−0.001 (6)
C6R	0.28 (2)	0.062 (12)	0.094 (14)	0.048 (15)	−0.010 (15)	−0.023 (11)
C7R	0.125 (13)	0.041 (7)	0.142 (16)	0.019 (7)	−0.012 (11)	−0.024 (9)
C8R	0.121 (14)	0.106 (13)	0.168 (17)	−0.021 (11)	−0.029 (13)	0.036 (12)
C9R	0.150 (16)	0.055 (8)	0.140 (18)	0.024 (9)	−0.062 (15)	0.002 (9)
C10R	0.057 (8)	0.056 (7)	0.078 (8)	0.030 (5)	0.009 (7)	−0.014 (6)
C11R	0.119 (14)	0.030 (5)	0.059 (8)	0.022 (7)	0.008 (8)	0.003 (5)
C12R	0.051 (6)	0.070 (9)	0.056 (10)	0.004 (7)	−0.002 (6)	0.024 (8)
C13R	0.147 (16)	0.040 (7)	0.061 (9)	0.029 (8)	0.015 (9)	−0.021 (6)
C14R	0.076 (10)	0.035 (6)	0.048 (8)	0.018 (6)	0.004 (7)	−0.003 (5)
C15R	0.046 (5)	0.048 (5)	0.049 (5)	0.010 (4)	0.001 (4)	−0.002 (4)
C16R	0.033 (7)	0.041 (5)	0.046 (5)	−0.006 (5)	−0.010 (5)	0.006 (4)
C17R	0.021 (6)	0.040 (5)	0.087 (8)	−0.002 (4)	0.003 (5)	−0.015 (5)
C18R	0.046 (7)	0.037 (6)	0.062 (7)	0.010 (4)	−0.005 (5)	0.017 (5)
C19R	0.087 (12)	0.108 (11)	0.183 (15)	0.052 (10)	0.046 (11)	0.002 (11)
O2R	0.093 (17)	0.072 (9)	0.066 (8)	0.020 (7)	−0.007 (7)	0.004 (6)
O3R	0.072 (6)	0.032 (6)	0.051 (5)	0.016 (5)	−0.009 (4)	−0.007 (5)
O1P	0.135 (15)	0.096 (8)	0.164 (12)	−0.004 (9)	−0.077 (10)	−0.002 (8)
C1P	0.110 (14)	0.063 (9)	0.063 (10)	0.010 (9)	−0.022 (9)	0.010 (7)
C2P	0.152 (12)	0.063 (7)	0.067 (6)	0.038 (8)	0.010 (7)	0.021 (5)
C3P	0.079 (9)	0.086 (10)	0.147 (14)	0.010 (8)	0.027 (10)	0.035 (12)
C4P	0.089 (11)	0.080 (10)	0.093 (10)	−0.017 (8)	−0.032 (9)	0.010 (8)
C5P	0.118 (12)	0.078 (14)	0.070 (8)	0.035 (9)	0.015 (8)	0.012 (8)
C6P	0.27 (2)	0.067 (13)	0.104 (16)	0.043 (15)	−0.032 (16)	−0.010 (11)
C7P	0.123 (14)	0.043 (7)	0.187 (19)	0.018 (8)	0.029 (14)	0.025 (9)
C8P	0.118 (15)	0.137 (16)	0.178 (19)	−0.029 (14)	−0.014 (14)	0.024 (15)
C9P	0.138 (13)	0.105 (13)	0.093 (10)	0.015 (10)	0.001 (9)	0.016 (9)
C10P	0.067 (11)	0.087 (9)	0.083 (8)	0.022 (7)	0.029 (7)	−0.006 (7)
C11P	0.063 (8)	0.092 (12)	0.106 (12)	0.014 (8)	−0.031 (8)	0.012 (9)
C12P	0.094 (10)	0.049 (7)	0.061 (10)	0.030 (7)	−0.003 (7)	−0.015 (7)
C13P	0.069 (7)	0.049 (6)	0.054 (7)	0.006 (5)	0.002 (6)	0.021 (5)
C14P	0.085 (10)	0.047 (8)	0.068 (10)	0.023 (7)	0.019 (8)	−0.005 (7)
C15P	0.043 (5)	0.047 (5)	0.047 (5)	0.004 (3)	0.000 (3)	0.008 (3)
C16P	0.035 (7)	0.077 (8)	0.059 (6)	−0.008 (5)	0.020 (5)	−0.003 (5)
C17P	0.028 (7)	0.057 (6)	0.074 (6)	−0.001 (5)	0.008 (5)	0.009 (5)
C18P	0.046 (6)	0.045 (5)	0.051 (5)	0.001 (4)	0.002 (4)	−0.008 (4)
C19P	0.081 (10)	0.116 (13)	0.196 (15)	0.031 (11)	0.051 (10)	0.035 (12)
O2P	0.098 (17)	0.062 (6)	0.054 (6)	0.024 (7)	0.013 (5)	0.014 (5)
O3P	0.105 (9)	0.047 (8)	0.089 (8)	0.007 (6)	−0.005 (6)	−0.024 (5)
N1R	0.065 (7)	0.049 (6)	0.054 (10)	0.016 (5)	−0.007 (5)	0.021 (6)
C20R	0.089 (17)	0.055 (14)	0.078 (16)	0.038 (12)	−0.005 (11)	0.005 (11)
C21R	0.127 (19)	0.078 (13)	0.080 (11)	−0.016 (11)	−0.030 (11)	−0.039 (11)
C22R	0.125 (18)	0.056 (11)	0.071 (11)	0.020 (11)	−0.023 (11)	−0.005 (9)
C23R	0.055 (10)	0.114 (19)	0.103 (10)	−0.010 (10)	0.018 (7)	0.005 (11)
C24R	0.074 (12)	0.085 (12)	0.162 (19)	0.024 (10)	0.004 (14)	0.014 (12)
C25R	0.080 (13)	0.080 (12)	0.106 (14)	0.012 (9)	0.006 (11)	0.011 (11)
C26R	0.110 (15)	0.118 (17)	0.079 (10)	0.025 (11)	0.015 (10)	0.006 (11)
C27R	0.061 (8)	0.100 (11)	0.086 (10)	0.019 (8)	0.019 (8)	0.026 (8)
N1P	0.069 (7)	0.059 (8)	0.030 (5)	0.011 (6)	−0.001 (4)	0.003 (6)
C20P	0.089 (16)	0.064 (15)	0.062 (10)	−0.029 (10)	0.010 (9)	0.001 (9)
C21P	0.097 (15)	0.111 (17)	0.15 (2)	−0.007 (12)	−0.030 (14)	0.063 (16)
C22P	0.031 (6)	0.068 (12)	0.109 (14)	−0.006 (6)	0.014 (6)	0.024 (10)
C23P	0.111 (16)	0.069 (12)	0.170 (18)	0.035 (11)	0.024 (13)	0.060 (12)
C24P	0.078 (13)	0.104 (15)	0.23 (3)	0.029 (11)	0.029 (18)	0.032 (17)
C25P	0.069 (9)	0.141 (15)	0.150 (17)	0.032 (9)	−0.012 (12)	−0.013 (13)
C26P	0.085 (12)	0.16 (3)	0.138 (17)	0.023 (15)	0.012 (11)	0.069 (17)
C27P	0.112 (17)	0.115 (15)	0.101 (14)	−0.003 (12)	−0.022 (12)	−0.001 (12)

Geometric parameters (Å, º)

O1R—C11R	1.235 (5)	C5P—C10P	1.555 (9)
C1R—C2R	1.514 (16)	C6P—C7P	1.548 (16)
C1R—C9R	1.514 (16)	C7P—C9P	1.488 (10)
C1R—C10R	1.545 (15)	C7P—C8P	1.531 (17)
C2R—C3R	1.510 (10)	C10P—C19P	1.478 (12)
C3R—C8R	1.519 (17)	C10P—C11P	1.543 (9)
C3R—C4R	1.528 (10)	C11P—C12P	1.510 (8)
C4R—C5R	1.500 (10)	C12P—C13P	1.378 (7)
C5R—C10R	1.539 (14)	C12P—C17P	1.386 (7)
C5R—C6R	1.551 (16)	C13P—C14P	1.376 (7)
C6R—C7R	1.497 (16)	C14P—C15P	1.393 (7)
C7R—C8R	1.491 (16)	C15P—C16P	1.395 (7)
C7R—C9R	1.494 (10)	C15P—C18P	1.475 (11)
C10R—C11R	1.508 (13)	C16P—C17P	1.361 (7)
C10R—C19R	1.518 (15)	C18P—O2P	1.257 (9)
C11R—C12R	1.503 (10)	C18P—O3P	1.271 (9)
C12R—C13R	1.372 (10)	N1R—C20R	1.481 (16)
C12R—C17R	1.378 (8)	C20R—C22R	1.510 (13)
C13R—C14R	1.376 (10)	C20R—C21R	1.530 (16)
C14R—C15R	1.378 (8)	C22R—C23R	1.374 (8)
C15R—C16R	1.376 (8)	C22R—C27R	1.386 (8)
C15R—C18R	1.498 (12)	C23R—C24R	1.401 (8)
C16R—C17R	1.394 (8)	C24R—C25R	1.329 (9)
C18R—O2R	1.247 (12)	C25R—C26R	1.361 (9)
C18R—O3R	1.289 (14)	C26R—C27R	1.368 (8)
O1P—C11P	1.472 (13)	N1P—C20P	1.480 (14)
C1P—C9P	1.510 (9)	C20P—C22P	1.486 (9)
C1P—C2P	1.528 (9)	C20P—C21P	1.514 (15)
C1P—C10P	1.552 (9)	C22P—C27P	1.366 (8)
C2P—C3P	1.505 (14)	C22P—C23P	1.382 (8)
C2P—C11P	1.512 (9)	C23P—C24P	1.375 (8)
C3P—C4P	1.506 (10)	C24P—C25P	1.375 (9)
C3P—C8P	1.512 (16)	C25P—C26P	1.356 (9)
C4P—C5P	1.529 (10)	C26P—C27P	1.401 (9)
C5P—C6P	1.552 (10)
C2R—C1R—C9R	108.3 (15)	C9P—C7P—C8P	103.9 (11)
C2R—C1R—C10R	109.2 (12)	C9P—C7P—C6P	108.5 (14)
C9R—C1R—C10R	112.0 (13)	C8P—C7P—C6P	114.6 (14)
C3R—C2R—C1R	109.5 (12)	C3P—C8P—C7P	110.6 (13)
C2R—C3R—C8R	111.6 (15)	C7P—C9P—C1P	108.4 (9)
C2R—C3R—C4R	105.4 (14)	C19P—C10P—C11P	120.6 (13)
C8R—C3R—C4R	110.4 (14)	C19P—C10P—C1P	118.9 (12)
C5R—C4R—C3R	109.7 (12)	C11P—C10P—C1P	83.9 (7)
C4R—C5R—C10R	108.7 (13)	C19P—C10P—C5P	113.3 (9)
C4R—C5R—C6R	110.9 (15)	C11P—C10P—C5P	109.5 (11)
C10R—C5R—C6R	107.7 (15)	C1P—C10P—C5P	106.8 (11)
C7R—C6R—C5R	111.1 (14)	O1P—C11P—C12P	100.8 (10)
C8R—C7R—C9R	108.8 (15)	O1P—C11P—C2P	105.0 (11)
C8R—C7R—C6R	107.1 (16)	C12P—C11P—C2P	125.9 (7)
C9R—C7R—C6R	111.5 (15)	O1P—C11P—C10P	110.1 (12)
C7R—C8R—C3R	110.7 (13)	C12P—C11P—C10P	127.1 (7)
C7R—C9R—C1R	110.1 (12)	C2P—C11P—C10P	86.3 (6)
C11R—C10R—C19R	107.6 (14)	C13P—C12P—C17P	117.0 (4)
C11R—C10R—C5R	111.0 (11)	C13P—C12P—C11P	119.6 (7)
C19R—C10R—C5R	111.3 (15)	C17P—C12P—C11P	123.4 (7)
C11R—C10R—C1R	108.7 (11)	C14P—C13P—C12P	121.6 (5)
C19R—C10R—C1R	111.0 (15)	C13P—C14P—C15P	121.2 (5)
C5R—C10R—C1R	107.2 (12)	C14P—C15P—C16P	116.9 (5)
O1R—C11R—C12R	115.4 (13)	C14P—C15P—C18P	122.3 (9)
O1R—C11R—C10R	115.8 (13)	C16P—C15P—C18P	120.8 (8)
C12R—C11R—C10R	127.2 (8)	C17P—C16P—C15P	121.0 (5)
C13R—C12R—C17R	119.5 (6)	C16P—C17P—C12P	122.2 (5)
C13R—C12R—C11R	116.4 (8)	O2P—C18P—O3P	121.3 (14)
C17R—C12R—C11R	124.1 (8)	O2P—C18P—C15P	118.8 (10)
C12R—C13R—C14R	120.9 (5)	O3P—C18P—C15P	118.5 (10)
C13R—C14R—C15R	120.5 (6)	N1R—C20R—C22R	108.9 (13)
C16R—C15R—C14R	118.7 (6)	N1R—C20R—C21R	109.1 (16)
C16R—C15R—C18R	122.0 (10)	C22R—C20R—C21R	114.2 (11)
C14R—C15R—C18R	119.0 (10)	C23R—C22R—C27R	117.6 (7)
C15R—C16R—C17R	121.0 (5)	C23R—C22R—C20R	120.7 (13)
C12R—C17R—C16R	119.2 (6)	C27R—C22R—C20R	121.7 (13)
O2R—C18R—O3R	122.7 (13)	C22R—C23R—C24R	120.9 (7)
O2R—C18R—C15R	118.7 (13)	C25R—C24R—C23R	118.9 (7)
O3R—C18R—C15R	117.9 (11)	C24R—C25R—C26R	122.2 (7)
C9P—C1P—C2P	120.2 (10)	C25R—C26R—C27R	119.1 (8)
C9P—C1P—C10P	119.6 (9)	C26R—C27R—C22R	121.2 (7)
C2P—C1P—C10P	85.5 (6)	N1P—C20P—C22P	113.6 (13)
C3P—C2P—C11P	114.8 (9)	N1P—C20P—C21P	106.6 (15)
C3P—C2P—C1P	110.7 (9)	C22P—C20P—C21P	115.0 (10)
C11P—C2P—C1P	85.8 (7)	C27P—C22P—C23P	119.2 (7)
C2P—C3P—C4P	108.4 (11)	C27P—C22P—C20P	120.5 (12)
C2P—C3P—C8P	109.4 (13)	C23P—C22P—C20P	120.2 (11)
C4P—C3P—C8P	110.7 (15)	C24P—C23P—C22P	121.0 (7)
C3P—C4P—C5P	104.2 (12)	C25P—C24P—C23P	118.9 (7)
C4P—C5P—C6P	105.7 (8)	C26P—C25P—C24P	121.5 (7)
C4P—C5P—C10P	111.1 (12)	C25P—C26P—C27P	119.2 (7)
C6P—C5P—C10P	114.2 (13)	C22P—C27P—C26P	120.3 (7)
C7P—C6P—C5P	108.1 (11)

(74.5P)

Crystal data

C27H33NO3	Dx = 1.209 Mg m^−3
Mr = 419.54	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1334 reflections
a = 12.053 (2) Å	θ = 6–19°
b = 29.385 (6) Å	µ = 0.08 mm^−1
c = 6.5093 (10) Å	T = 293 K
V = 2305.4 (7) Å^3	Block, colourless
Z = 4	0.56 × 0.41 × 0.20 mm
F(000) = 904

Data collection

Kuma KM4CCD diffractometer	2766 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.129
Graphite monochromator	θmax = 25.0°, θmin = 6.0°
ω scans	h = −14→13
10827 measured reflections	k = −34→34
3999 independent reflections	l = −7→6

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.119	w = 1/[σ^2(Fo^2) + (0.1395P)^2 + 1.2085P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.319	(Δ/σ)max < 0.001
S = 1.14	Δρmax = 0.20 e Å^−3
3999 reflections	Δρmin = −0.22 e Å^−3
406 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
216 restraints	Extinction coefficient: 0.25 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: The absolute configuration was assigned to agree with that from Leibovitch M. et all, 1997; 1998
Secondary atom site location: inferred from neighbouring sites

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1R	0.413 (2)	0.2153 (9)	0.462 (3)	0.097 (8)*	0.255 (10)
C1R	0.4004 (19)	0.3050 (8)	0.531 (4)	0.065 (9)*	0.255 (10)
H1R	0.3507	0.2934	0.4245	0.078*	0.255 (10)
C2R	0.5166 (17)	0.3113 (9)	0.447 (3)	0.092 (8)*	0.255 (10)
H2AR	0.5137	0.3322	0.3317	0.110*	0.255 (10)
H2BR	0.5434	0.2823	0.3961	0.110*	0.255 (10)
C3R	0.5975 (19)	0.3294 (9)	0.605 (3)	0.079 (9)*	0.255 (10)
H3R	0.6718	0.3329	0.5463	0.095*	0.255 (10)
C4R	0.597 (2)	0.2940 (12)	0.777 (5)	0.102 (15)*	0.255 (10)
H4AR	0.6166	0.2645	0.7210	0.123*	0.255 (10)
H4BR	0.6524	0.3021	0.8790	0.123*	0.255 (10)
C5R	0.485 (2)	0.2913 (9)	0.877 (4)	0.084 (12)*	0.255 (10)
H5R	0.4892	0.2708	0.9953	0.101*	0.255 (10)
C6R	0.443 (4)	0.3384 (11)	0.948 (4)	0.162 (17)*	0.255 (10)
H6AR	0.3704	0.3353	1.0099	0.195*	0.255 (10)
H6BR	0.4933	0.3508	1.0503	0.195*	0.255 (10)
C7R	0.437 (2)	0.3702 (9)	0.766 (4)	0.100 (10)*	0.255 (10)
H7R	0.4092	0.3999	0.8108	0.120*	0.255 (10)
C8R	0.553 (2)	0.3752 (9)	0.685 (5)	0.103 (11)*	0.255 (10)
H8AR	0.6006	0.3864	0.7939	0.124*	0.255 (10)
H8BR	0.5534	0.3974	0.5748	0.124*	0.255 (10)
C9R	0.358 (2)	0.3501 (9)	0.614 (5)	0.120 (15)*	0.255 (10)
H9AR	0.3474	0.3712	0.5015	0.144*	0.255 (10)
H9BR	0.2866	0.3454	0.6801	0.144*	0.255 (10)
C10R	0.404 (2)	0.2718 (7)	0.718 (4)	0.061 (8)*	0.255 (10)
C11R	0.439 (3)	0.2249 (7)	0.641 (3)	0.062 (7)*	0.255 (10)
C12R	0.490 (2)	0.1873 (6)	0.767 (3)	0.106 (14)*	0.255 (10)
C13R	0.576 (3)	0.1638 (10)	0.676 (4)	0.10 (2)*	0.255 (10)
H13R	0.5990	0.1716	0.5445	0.119*	0.255 (10)
C14R	0.628 (3)	0.1290 (12)	0.779 (4)	0.056 (12)*	0.255 (10)
H14R	0.6863	0.1136	0.7164	0.068*	0.255 (10)
C15R	0.594 (3)	0.1168 (10)	0.974 (4)	0.047 (11)*	0.255 (10)
C16R	0.509 (3)	0.1405 (10)	1.065 (4)	0.067 (13)*	0.255 (10)
H16R	0.4874	0.1329	1.1973	0.081*	0.255 (10)
C17R	0.456 (2)	0.1757 (8)	0.961 (3)	0.055 (9)*	0.255 (10)
H17R	0.3970	0.1911	1.0226	0.066*	0.255 (10)
C18R	0.651 (4)	0.0787 (12)	1.083 (4)	0.050 (13)*	0.255 (10)
C19R	0.288 (3)	0.264 (2)	0.807 (8)	0.15 (2)*	0.255 (10)
H19A	0.2588	0.2923	0.8579	0.225*	0.255 (10)
H19B	0.2922	0.2424	0.9174	0.225*	0.255 (10)
H19C	0.2397	0.2524	0.7017	0.225*	0.255 (10)
O2R	0.655 (3)	0.0796 (12)	1.276 (4)	0.064 (9)*	0.255 (10)
O3R	0.699 (3)	0.0489 (10)	0.975 (6)	0.062 (10)*	0.255 (10)
O1P	0.3616 (8)	0.2082 (3)	0.5291 (16)	0.123 (3)	0.745 (10)
HO1P	0.3948	0.1907	0.4524	0.185*	0.745 (10)
C1P	0.3894 (11)	0.2963 (4)	0.539 (2)	0.110 (6)	0.745 (10)
H1P	0.3303	0.2837	0.4528	0.132*	0.745 (10)
C2P	0.4968 (8)	0.2669 (2)	0.5174 (12)	0.098 (3)	0.745 (10)
H2P	0.5109	0.2555	0.3783	0.118*	0.745 (10)
C3P	0.5928 (9)	0.2917 (4)	0.613 (2)	0.120 (4)	0.745 (10)
H3P	0.6622	0.2779	0.5662	0.145*	0.745 (10)
C4P	0.5860 (11)	0.2878 (4)	0.843 (2)	0.107 (4)	0.745 (10)
H4AP	0.6380	0.3084	0.9080	0.128*	0.745 (10)
H4BP	0.6022	0.2570	0.8866	0.128*	0.745 (10)
C5P	0.4674 (11)	0.3006 (4)	0.8955 (17)	0.108 (5)	0.745 (10)
H5P	0.4525	0.2932	1.0396	0.130*	0.745 (10)
C6P	0.4639 (16)	0.3531 (4)	0.867 (2)	0.154 (6)	0.745 (10)
H6AP	0.5187	0.3673	0.9548	0.185*	0.745 (10)
H6BP	0.3913	0.3645	0.9052	0.185*	0.745 (10)
C7P	0.4882 (13)	0.3654 (4)	0.638 (2)	0.141 (5)	0.745 (10)
H7P	0.4948	0.3984	0.6210	0.169*	0.745 (10)
C8P	0.5902 (11)	0.3410 (5)	0.547 (3)	0.160 (8)	0.745 (10)
H8AP	0.5875	0.3426	0.3980	0.191*	0.745 (10)
H8BP	0.6574	0.3561	0.5923	0.191*	0.745 (10)
C9P	0.3940 (12)	0.3475 (3)	0.515 (2)	0.119 (4)	0.745 (10)
H9AP	0.4038	0.3554	0.3718	0.143*	0.745 (10)
H9BP	0.3250	0.3609	0.5627	0.143*	0.745 (10)
C10P	0.3841 (9)	0.2750 (4)	0.7558 (16)	0.088 (4)	0.745 (10)
C11P	0.4431 (10)	0.2333 (3)	0.6590 (15)	0.083 (3)	0.745 (10)
C12P	0.5004 (6)	0.1951 (2)	0.7735 (9)	0.059 (2)	0.745 (10)
C13P	0.5795 (10)	0.1697 (4)	0.6727 (11)	0.073 (5)	0.745 (10)
H13P	0.6001	0.1778	0.5399	0.088*	0.745 (10)
C14P	0.6289 (13)	0.1325 (5)	0.7648 (16)	0.073 (6)	0.745 (10)
H14P	0.6795	0.1151	0.6913	0.088*	0.745 (10)
C15P	0.6034 (13)	0.1209 (4)	0.9670 (15)	0.063 (5)	0.745 (10)
C16P	0.5255 (13)	0.1471 (4)	1.0693 (13)	0.074 (4)	0.745 (10)
H16P	0.5049	0.1394	1.2026	0.088*	0.745 (10)
C17P	0.4782 (9)	0.1844 (3)	0.9753 (12)	0.069 (3)	0.745 (10)
H17P	0.4302	0.2028	1.0501	0.083*	0.745 (10)
C18P	0.6556 (15)	0.0806 (4)	1.0645 (17)	0.064 (6)	0.745 (10)
C19P	0.2728 (11)	0.2703 (7)	0.846 (3)	0.151 (8)	0.745 (10)
H19D	0.2787	0.2566	0.9797	0.226*	0.745 (10)
H19E	0.2277	0.2515	0.7594	0.226*	0.745 (10)
H19F	0.2393	0.2998	0.8589	0.226*	0.745 (10)
O2P	0.6523 (15)	0.0779 (5)	1.2576 (16)	0.098 (6)	0.745 (10)
O3P	0.6988 (15)	0.0503 (4)	0.951 (2)	0.087 (5)	0.745 (10)
N1R	0.641 (3)	0.0079 (11)	0.577 (6)	0.056 (9)*	0.255 (10)
H1NR	0.6916	−0.0102	0.5190	0.084*	0.255 (10)
H2NR	0.6574	0.0117	0.7090	0.084*	0.255 (10)
H3NR	0.6410	0.0347	0.5136	0.084*	0.255 (10)
C20R	0.530 (3)	−0.0133 (13)	0.558 (5)	0.057 (10)*	0.255 (10)
H20R	0.5303	−0.0421	0.6339	0.068*	0.255 (10)
C21R	0.509 (3)	−0.0235 (11)	0.333 (4)	0.066 (8)*	0.255 (10)
H21A	0.5688	−0.0419	0.2806	0.098*	0.255 (10)
H21B	0.5060	0.0045	0.2574	0.098*	0.255 (10)
H21C	0.4405	−0.0395	0.3186	0.098*	0.255 (10)
C22R	0.447 (2)	0.0178 (10)	0.655 (4)	0.059 (11)*	0.255 (10)
C23R	0.421 (3)	0.0599 (12)	0.576 (4)	0.088 (11)*	0.255 (10)
H23R	0.4561	0.0702	0.4579	0.105*	0.255 (10)
C24R	0.341 (4)	0.0874 (11)	0.673 (5)	0.102 (13)*	0.255 (10)
H24R	0.3235	0.1157	0.6185	0.122*	0.255 (10)
C25R	0.292 (3)	0.0728 (14)	0.843 (5)	0.115 (16)*	0.255 (10)
H25R	0.2409	0.0915	0.9083	0.138*	0.255 (10)
C26R	0.315 (4)	0.0311 (15)	0.925 (6)	0.105 (13)*	0.255 (10)
H26R	0.2790	0.0213	1.0433	0.126*	0.255 (10)
C27R	0.392 (4)	0.0042 (12)	0.832 (6)	0.084 (13)*	0.255 (10)
H27R	0.4083	−0.0241	0.8882	0.101*	0.255 (10)
N1P	0.6565 (9)	0.0168 (4)	0.5646 (18)	0.061 (3)	0.745 (10)
H1NP	0.7115	−0.0019	0.5304	0.091*	0.745 (10)
H2NP	0.6702	0.0289	0.6873	0.091*	0.745 (10)
H3NP	0.6513	0.0389	0.4714	0.091*	0.745 (10)
C20P	0.5507 (11)	−0.0089 (5)	0.572 (2)	0.076 (4)	0.745 (10)
H20P	0.5589	−0.0327	0.6766	0.092*	0.745 (10)
C21P	0.5323 (13)	−0.0324 (4)	0.3678 (19)	0.112 (5)	0.745 (10)
H21D	0.5944	−0.0518	0.3381	0.168*	0.745 (10)
H21E	0.5250	−0.0099	0.2615	0.168*	0.745 (10)
H21F	0.4659	−0.0503	0.3744	0.168*	0.745 (10)
C22P	0.4561 (10)	0.0207 (4)	0.6360 (19)	0.084 (6)	0.745 (10)
C23P	0.4211 (13)	0.0569 (4)	0.516 (3)	0.118 (6)	0.745 (10)
H23P	0.4567	0.0628	0.3918	0.141*	0.745 (10)
C24P	0.3348 (12)	0.0841 (5)	0.577 (3)	0.137 (7)	0.745 (10)
H24P	0.3106	0.1079	0.4939	0.165*	0.745 (10)
C25P	0.2843 (12)	0.0756 (5)	0.763 (3)	0.148 (8)	0.745 (10)
H25P	0.2272	0.0945	0.8077	0.177*	0.745 (10)
C26P	0.3163 (17)	0.0403 (8)	0.883 (3)	0.147 (7)	0.745 (10)
H26P	0.2797	0.0343	1.0057	0.176*	0.745 (10)
C27P	0.4050 (15)	0.0129 (6)	0.820 (2)	0.119 (6)	0.745 (10)
H27P	0.4293	−0.0107	0.9041	0.142*	0.745 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1P	0.132 (7)	0.087 (5)	0.151 (8)	−0.002 (5)	−0.057 (7)	−0.005 (5)
C1P	0.133 (11)	0.082 (8)	0.116 (10)	0.006 (7)	−0.043 (8)	0.014 (7)
C2P	0.139 (9)	0.072 (5)	0.083 (6)	0.020 (6)	0.010 (6)	0.016 (4)
C3P	0.089 (7)	0.088 (8)	0.184 (14)	−0.003 (6)	0.024 (8)	0.010 (8)
C4P	0.128 (11)	0.066 (6)	0.128 (10)	−0.003 (6)	−0.043 (8)	−0.008 (7)
C5P	0.184 (15)	0.061 (6)	0.078 (6)	0.017 (8)	−0.017 (7)	0.014 (5)
C6P	0.251 (19)	0.087 (8)	0.123 (10)	0.010 (10)	0.011 (12)	−0.041 (8)
C7P	0.161 (13)	0.072 (7)	0.189 (14)	0.027 (8)	0.012 (13)	0.061 (8)
C8P	0.122 (11)	0.140 (13)	0.217 (19)	−0.003 (10)	0.010 (11)	0.081 (14)
C9P	0.160 (12)	0.067 (6)	0.130 (10)	0.028 (7)	−0.013 (10)	0.032 (6)
C10P	0.088 (7)	0.082 (6)	0.095 (7)	0.010 (5)	0.011 (6)	0.003 (5)
C11P	0.089 (6)	0.076 (6)	0.084 (6)	0.012 (5)	−0.016 (5)	0.003 (5)
C12P	0.075 (5)	0.048 (3)	0.054 (4)	0.005 (3)	−0.004 (3)	0.007 (3)
C13P	0.113 (10)	0.058 (5)	0.048 (5)	0.023 (4)	0.010 (4)	0.020 (3)
C14P	0.104 (10)	0.055 (6)	0.061 (6)	0.017 (4)	0.017 (4)	0.011 (4)
C15P	0.085 (8)	0.049 (5)	0.054 (6)	0.016 (4)	0.004 (4)	0.012 (3)
C16P	0.109 (9)	0.058 (5)	0.054 (5)	0.008 (6)	0.025 (4)	0.011 (4)
C17P	0.067 (5)	0.037 (4)	0.104 (7)	0.006 (4)	0.019 (5)	−0.006 (4)
C18P	0.089 (9)	0.047 (5)	0.054 (5)	0.001 (4)	−0.008 (4)	0.010 (4)
C19P	0.099 (8)	0.155 (14)	0.198 (17)	0.029 (9)	0.041 (10)	0.061 (13)
O2P	0.161 (10)	0.072 (5)	0.061 (5)	0.022 (4)	0.000 (4)	0.018 (4)
O3P	0.125 (9)	0.060 (5)	0.077 (6)	0.032 (4)	−0.007 (4)	−0.004 (3)
N1P	0.072 (5)	0.042 (4)	0.067 (5)	−0.002 (4)	−0.007 (4)	0.004 (4)
C20P	0.088 (9)	0.061 (6)	0.080 (6)	0.006 (6)	−0.013 (5)	0.005 (4)
C21P	0.125 (10)	0.079 (7)	0.131 (10)	0.001 (6)	−0.053 (8)	0.022 (7)
C22P	0.073 (6)	0.066 (7)	0.115 (10)	−0.009 (4)	0.015 (5)	0.017 (5)
C23P	0.114 (9)	0.071 (7)	0.168 (13)	0.028 (6)	0.052 (10)	0.046 (8)
C24P	0.087 (8)	0.100 (9)	0.22 (2)	0.032 (7)	0.035 (12)	0.025 (12)
C25P	0.084 (8)	0.118 (12)	0.24 (2)	0.003 (7)	0.029 (14)	−0.063 (14)
C26P	0.126 (12)	0.17 (2)	0.144 (14)	0.022 (12)	0.042 (11)	−0.008 (13)
C27P	0.092 (8)	0.145 (13)	0.119 (11)	−0.006 (10)	0.017 (7)	0.000 (9)

Geometric parameters (Å, º)

O1R—C11R	1.236 (17)	C5P—C6P	1.552 (9)
C1R—C2R	1.515 (18)	C6P—C7P	1.560 (14)
C1R—C9R	1.521 (18)	C7P—C9P	1.484 (15)
C1R—C10R	1.556 (18)	C7P—C8P	1.543 (15)
C2R—C3R	1.515 (18)	C10P—C19P	1.472 (13)
C3R—C4R	1.527 (10)	C10P—C11P	1.550 (12)
C3R—C8R	1.541 (18)	C11P—C12P	1.515 (7)
C4R—C5R	1.498 (10)	C12P—C13P	1.376 (6)
C5R—C10R	1.539 (17)	C12P—C17P	1.377 (6)
C5R—C6R	1.544 (19)	C13P—C14P	1.382 (6)
C6R—C7R	1.513 (19)	C14P—C15P	1.394 (6)
C7R—C9R	1.491 (18)	C15P—C16P	1.385 (6)
C7R—C8R	1.500 (18)	C15P—C18P	1.485 (7)
C10R—C11R	1.525 (16)	C16P—C17P	1.379 (6)
C10R—C19R	1.533 (18)	C18P—O2P	1.260 (7)
C11R—C12R	1.507 (11)	C18P—O3P	1.269 (7)
C12R—C17R	1.373 (14)	N1R—C20R	1.481 (19)
C12R—C13R	1.379 (14)	C20R—C22R	1.497 (17)
C13R—C14R	1.373 (12)	C20R—C21R	1.515 (19)
C14R—C15R	1.381 (13)	C22R—C23R	1.376 (9)
C15R—C16R	1.372 (13)	C22R—C27R	1.386 (9)
C15R—C18R	1.492 (10)	C23R—C24R	1.401 (9)
C16R—C17R	1.396 (12)	C24R—C25R	1.328 (9)
C18R—O2R	1.252 (9)	C25R—C26R	1.365 (9)
C18R—O3R	1.265 (9)	C26R—C27R	1.363 (9)
O1P—C11P	1.493 (11)	N1P—C20P	1.484 (13)
C1P—C9P	1.514 (13)	C20P—C22P	1.493 (10)
C1P—C10P	1.543 (13)	C20P—C21P	1.514 (13)
C1P—C2P	1.563 (13)	C22P—C27P	1.368 (8)
C2P—C11P	1.498 (11)	C22P—C23P	1.385 (8)
C2P—C3P	1.503 (12)	C23P—C24P	1.372 (8)
C3P—C4P	1.499 (9)	C24P—C25P	1.381 (8)
C3P—C8P	1.510 (14)	C25P—C26P	1.354 (8)
C4P—C5P	1.518 (9)	C26P—C27P	1.399 (8)
C5P—C10P	1.550 (9)
C2R—C1R—C9R	109.5 (19)	C9P—C7P—C8P	103.8 (11)
C2R—C1R—C10R	109.5 (17)	C9P—C7P—C6P	106.6 (12)
C9R—C1R—C10R	106.1 (18)	C8P—C7P—C6P	114.1 (11)
C1R—C2R—C3R	113.0 (16)	C3P—C8P—C7P	110.6 (10)
C2R—C3R—C4R	104.9 (19)	C7P—C9P—C1P	109.0 (9)
C2R—C3R—C8R	108.2 (18)	C19P—C10P—C1P	116.2 (11)
C4R—C3R—C8R	110.2 (19)	C19P—C10P—C11P	120.5 (11)
C5R—C4R—C3R	110.9 (18)	C1P—C10P—C11P	86.0 (7)
C4R—C5R—C10R	107 (2)	C19P—C10P—C5P	113.6 (11)
C4R—C5R—C6R	112 (2)	C1P—C10P—C5P	108.1 (8)
C10R—C5R—C6R	109 (2)	C11P—C10P—C5P	109.0 (9)
C7R—C6R—C5R	109.6 (19)	O1P—C11P—C2P	105.2 (7)
C9R—C7R—C8R	114 (2)	O1P—C11P—C12P	102.2 (6)
C9R—C7R—C6R	108 (2)	C2P—C11P—C12P	126.5 (8)
C8R—C7R—C6R	107 (2)	O1P—C11P—C10P	108.6 (8)
C7R—C8R—C3R	111.0 (17)	C2P—C11P—C10P	85.9 (6)
C7R—C9R—C1R	111.4 (18)	C12P—C11P—C10P	126.5 (7)
C11R—C10R—C19R	104 (2)	C13P—C12P—C17P	117.8 (4)
C11R—C10R—C5R	112.4 (18)	C13P—C12P—C11P	118.8 (5)
C19R—C10R—C5R	112 (2)	C17P—C12P—C11P	123.3 (5)
C11R—C10R—C1R	108.6 (16)	C12P—C13P—C14P	121.3 (4)
C19R—C10R—C1R	111 (2)	C13P—C14P—C15P	120.6 (4)
C5R—C10R—C1R	108.0 (16)	C16P—C15P—C14P	117.9 (4)
O1R—C11R—C12R	116.6 (16)	C16P—C15P—C18P	121.7 (5)
O1R—C11R—C10R	116.4 (17)	C14P—C15P—C18P	120.4 (5)
C12R—C11R—C10R	126.7 (14)	C17P—C16P—C15P	120.6 (4)
C17R—C12R—C13R	119.7 (7)	C12P—C17P—C16P	121.6 (4)
C17R—C12R—C11R	124.0 (11)	O2P—C18P—O3P	123.4 (8)
C13R—C12R—C11R	116.3 (10)	O2P—C18P—C15P	117.6 (6)
C14R—C13R—C12R	120.6 (8)	O3P—C18P—C15P	119.0 (6)
C13R—C14R—C15R	120.5 (8)	N1R—C20R—C22R	108 (2)
C16R—C15R—C14R	118.8 (7)	N1R—C20R—C21R	108 (2)
C16R—C15R—C18R	121.2 (10)	C22R—C20R—C21R	114.6 (15)
C14R—C15R—C18R	119.9 (10)	C23R—C22R—C27R	117.5 (7)
C15R—C16R—C17R	121.0 (8)	C23R—C22R—C20R	123.0 (18)
C12R—C17R—C16R	119.3 (8)	C27R—C22R—C20R	119.5 (18)
O2R—C18R—O3R	123.9 (11)	C22R—C23R—C24R	120.4 (8)
O2R—C18R—C15R	118.5 (9)	C25R—C24R—C23R	119.6 (8)
O3R—C18R—C15R	117.5 (9)	C24R—C25R—C26R	121.7 (8)
C9P—C1P—C10P	119.9 (11)	C27R—C26R—C25R	119.0 (8)
C9P—C1P—C2P	120.6 (11)	C26R—C27R—C22R	121.7 (8)
C10P—C1P—C2P	83.9 (6)	N1P—C20P—C22P	111.6 (9)
C11P—C2P—C3P	113.4 (8)	N1P—C20P—C21P	109.2 (10)
C11P—C2P—C1P	87.1 (7)	C22P—C20P—C21P	113.5 (11)
C3P—C2P—C1P	109.4 (8)	C27P—C22P—C23P	119.2 (6)
C4P—C3P—C2P	109.6 (8)	C27P—C22P—C20P	119.3 (9)
C4P—C3P—C8P	110.9 (12)	C23P—C22P—C20P	121.5 (9)
C2P—C3P—C8P	109.2 (10)	C24P—C23P—C22P	121.0 (7)
C3P—C4P—C5P	105.0 (9)	C23P—C24P—C25P	118.9 (7)
C4P—C5P—C10P	110.9 (9)	C26P—C25P—C24P	121.2 (7)
C4P—C5P—C6P	104.1 (10)	C25P—C26P—C27P	119.4 (7)
C10P—C5P—C6P	113.2 (9)	C22P—C27P—C26P	120.2 (7)
C5P—C6P—C7P	110.0 (8)

(80.1P)

Crystal data

C27H33NO3	Dx = 1.209 Mg m^−3
Mr = 419.54	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1317 reflections
a = 12.140 (3) Å	θ = 6–19°
b = 29.258 (6) Å	µ = 0.08 mm^−1
c = 6.4918 (11) Å	T = 293 K
V = 2305.8 (8) Å^3	Block, colourless
Z = 4	0.56 × 0.41 × 0.20 mm
F(000) = 904

Data collection

Kuma KM4CCD diffractometer	2858 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.125
Graphite monochromator	θmax = 25.0°, θmin = 6.0°
ω scans	h = −14→13
10838 measured reflections	k = −34→34
4010 independent reflections	l = −7→6

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.113	w = 1/[σ^2(Fo^2) + (0.1187P)^2 + 1.4128P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.297	(Δ/σ)max = 0.001
S = 1.14	Δρmax = 0.20 e Å^−3
4010 reflections	Δρmin = −0.19 e Å^−3
406 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
222 restraints	Extinction coefficient: 0.22 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: The absolute configuration was assigned to agree with that from Leibovitch M. et all, 1997; 1998
Secondary atom site location: inferred from neighbouring sites

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1R	0.417 (3)	0.2152 (10)	0.467 (3)	0.120 (12)*	0.199 (9)
C1R	0.398 (2)	0.3050 (9)	0.541 (5)	0.10 (3)*	0.199 (9)
H1R	0.3480	0.2928	0.4362	0.117*	0.199 (9)
C2R	0.512 (2)	0.3117 (10)	0.449 (4)	0.087 (10)*	0.199 (9)
H2AR	0.5393	0.2827	0.3971	0.105*	0.199 (9)
H2BR	0.5075	0.3328	0.3338	0.105*	0.199 (9)
C3R	0.591 (2)	0.3303 (10)	0.608 (4)	0.071 (10)*	0.199 (9)
H3R	0.6653	0.3340	0.5500	0.085*	0.199 (9)
C4R	0.592 (3)	0.2956 (13)	0.785 (6)	0.12 (3)*	0.199 (9)
H4AR	0.6132	0.2659	0.7313	0.145*	0.199 (9)
H4BR	0.6470	0.3046	0.8856	0.145*	0.199 (9)
C5R	0.482 (3)	0.2918 (11)	0.889 (5)	0.12 (3)*	0.199 (9)
H5R	0.4871	0.2712	1.0075	0.141*	0.199 (9)
C6R	0.437 (4)	0.3389 (12)	0.956 (5)	0.161 (18)*	0.199 (9)
H6AR	0.3639	0.3353	1.0123	0.193*	0.199 (9)
H6BR	0.4843	0.3517	1.0614	0.193*	0.199 (9)
C7R	0.434 (2)	0.3705 (10)	0.772 (5)	0.093 (11)*	0.199 (9)
H7R	0.4057	0.4004	0.8161	0.112*	0.199 (9)
C8R	0.547 (2)	0.3760 (9)	0.692 (5)	0.087 (11)*	0.199 (9)
H8AR	0.5951	0.3868	0.8013	0.104*	0.199 (9)
H8BR	0.5477	0.3986	0.5826	0.104*	0.199 (9)
C9R	0.357 (2)	0.3506 (10)	0.617 (5)	0.102 (13)*	0.199 (9)
H9AR	0.3493	0.3714	0.5010	0.123*	0.199 (9)
H9BR	0.2843	0.3467	0.6779	0.123*	0.199 (9)
C10R	0.404 (2)	0.2718 (8)	0.726 (4)	0.062 (10)*	0.199 (9)
C11R	0.441 (3)	0.2251 (8)	0.649 (4)	0.052 (10)*	0.199 (9)
C12R	0.494 (2)	0.1875 (7)	0.771 (4)	0.10 (2)*	0.199 (9)
C13R	0.576 (3)	0.1635 (13)	0.667 (4)	0.10 (3)*	0.199 (9)
H13R	0.5927	0.1712	0.5319	0.124*	0.199 (9)
C14R	0.631 (3)	0.1287 (15)	0.762 (5)	0.057 (8)*	0.199 (9)
H14R	0.6864	0.1135	0.6914	0.069*	0.199 (9)
C15R	0.604 (3)	0.1159 (11)	0.962 (5)	0.052 (8)*	0.199 (9)
C16R	0.525 (3)	0.1402 (12)	1.065 (4)	0.066 (8)*	0.199 (9)
H16R	0.5097	0.1329	1.2011	0.079*	0.199 (9)
C17R	0.468 (3)	0.1757 (10)	0.968 (4)	0.043 (9)*	0.199 (9)
H17R	0.4125	0.1912	1.0383	0.052*	0.199 (9)
C18R	0.667 (4)	0.0769 (13)	1.057 (4)	0.070 (17)*	0.199 (9)
C19R	0.290 (3)	0.262 (2)	0.818 (9)	0.156 (19)*	0.199 (9)
H19A	0.2585	0.2894	0.8707	0.233*	0.199 (9)
H19B	0.2973	0.2398	0.9276	0.233*	0.199 (9)
H19C	0.2428	0.2493	0.7129	0.233*	0.199 (9)
O2R	0.686 (2)	0.0791 (10)	1.247 (4)	0.066 (9)*	0.199 (9)
O3R	0.719 (3)	0.0512 (13)	0.935 (5)	0.066 (12)*	0.199 (9)
O1P	0.3579 (7)	0.20839 (19)	0.5336 (13)	0.122 (3)	0.801 (9)
HO1P	0.3898	0.1907	0.4558	0.182*	0.801 (9)
C1P	0.3893 (8)	0.2961 (4)	0.5334 (14)	0.086 (4)	0.801 (9)
H1P	0.3303	0.2831	0.4487	0.103*	0.801 (9)
C2P	0.4935 (6)	0.2668 (2)	0.5123 (10)	0.091 (3)	0.801 (9)
H2P	0.5065	0.2550	0.3733	0.109*	0.801 (9)
C3P	0.5892 (8)	0.2909 (3)	0.6046 (18)	0.109 (3)	0.801 (9)
H3P	0.6572	0.2767	0.5544	0.130*	0.801 (9)
C4P	0.5853 (9)	0.2870 (4)	0.8344 (19)	0.107 (5)	0.801 (9)
H4AP	0.6388	0.3071	0.8980	0.129*	0.801 (9)
H4BP	0.5999	0.2558	0.8781	0.129*	0.801 (9)
C5P	0.4687 (9)	0.3011 (3)	0.8897 (13)	0.096 (4)	0.801 (9)
H5P	0.4550	0.2940	1.0350	0.115*	0.801 (9)
C6P	0.4646 (13)	0.3535 (3)	0.8587 (18)	0.137 (5)	0.801 (9)
H6AP	0.5202	0.3681	0.9438	0.164*	0.801 (9)
H6BP	0.3930	0.3651	0.8999	0.164*	0.801 (9)
C7P	0.4859 (11)	0.3651 (3)	0.6275 (18)	0.124 (4)	0.801 (9)
H7P	0.4927	0.3982	0.6084	0.149*	0.801 (9)
C8P	0.5881 (9)	0.3404 (4)	0.542 (2)	0.142 (6)	0.801 (9)
H8AP	0.5884	0.3426	0.3929	0.171*	0.801 (9)
H8BP	0.6541	0.3553	0.5932	0.171*	0.801 (9)
C9P	0.3927 (9)	0.3470 (3)	0.5052 (18)	0.112 (4)	0.801 (9)
H9AP	0.4026	0.3545	0.3608	0.134*	0.801 (9)
H9BP	0.3241	0.3605	0.5518	0.134*	0.801 (9)
C10P	0.3835 (7)	0.2758 (3)	0.7549 (12)	0.086 (3)	0.801 (9)
C11P	0.4391 (8)	0.2334 (3)	0.6569 (14)	0.081 (4)	0.801 (9)
C12P	0.4981 (6)	0.1952 (2)	0.7728 (9)	0.061 (3)	0.801 (9)
C13P	0.5773 (8)	0.1701 (4)	0.6728 (11)	0.070 (4)	0.801 (9)
H13P	0.5984	0.1782	0.5399	0.084*	0.801 (9)
C14P	0.6263 (12)	0.1328 (4)	0.7685 (14)	0.069 (3)	0.801 (9)
H14P	0.6785	0.1157	0.6974	0.083*	0.801 (9)
C15P	0.5983 (9)	0.1207 (3)	0.9690 (12)	0.055 (2)	0.801 (9)
C16P	0.5190 (10)	0.1467 (3)	1.0694 (12)	0.071 (3)	0.801 (9)
H16P	0.4970	0.1388	1.2019	0.086*	0.801 (9)
C17P	0.4727 (10)	0.1841 (3)	0.9730 (13)	0.078 (4)	0.801 (9)
H17P	0.4232	0.2022	1.0454	0.094*	0.801 (9)
C18P	0.6513 (10)	0.0810 (3)	1.0719 (10)	0.054 (3)	0.801 (9)
C19P	0.2743 (9)	0.2726 (5)	0.855 (3)	0.147 (6)	0.801 (9)
H19D	0.2821	0.2588	0.9879	0.220*	0.801 (9)
H19E	0.2263	0.2543	0.7711	0.220*	0.801 (9)
H19F	0.2437	0.3027	0.8694	0.220*	0.801 (9)
O2P	0.6473 (8)	0.0786 (2)	1.2656 (8)	0.076 (2)	0.801 (9)
O3P	0.6933 (10)	0.0494 (3)	0.9619 (12)	0.072 (2)	0.801 (9)
N1R	0.658 (2)	0.0155 (13)	0.530 (5)	0.038 (7)*	0.199 (9)
H1NR	0.7041	−0.0044	0.4726	0.057*	0.199 (9)
H2NR	0.6883	0.0270	0.6437	0.057*	0.199 (9)
H3NR	0.6442	0.0380	0.4417	0.057*	0.199 (9)
C20R	0.554 (3)	−0.0079 (13)	0.584 (6)	0.057 (15)*	0.199 (9)
H20R	0.5724	−0.0306	0.6891	0.068*	0.199 (9)
C21R	0.513 (5)	−0.035 (2)	0.396 (9)	0.10 (3)*	0.199 (9)
H21A	0.5725	−0.0527	0.3417	0.156*	0.199 (9)
H21B	0.4883	−0.0136	0.2925	0.156*	0.199 (9)
H21C	0.4537	−0.0542	0.4361	0.156*	0.199 (9)
C22R	0.465 (2)	0.0215 (9)	0.672 (4)	0.048 (10)*	0.199 (9)
C23R	0.433 (2)	0.0621 (10)	0.585 (3)	0.053 (8)*	0.199 (9)
H23R	0.4677	0.0725	0.4659	0.064*	0.199 (9)
C24R	0.348 (3)	0.0881 (10)	0.673 (4)	0.078 (11)*	0.199 (9)
H24R	0.3261	0.1154	0.6120	0.093*	0.199 (9)
C25R	0.299 (3)	0.0734 (12)	0.843 (5)	0.089 (14)*	0.199 (9)
H25R	0.2437	0.0910	0.9022	0.107*	0.199 (9)
C26R	0.328 (3)	0.0332 (13)	0.935 (5)	0.080 (12)*	0.199 (9)
H26R	0.2926	0.0234	1.0532	0.096*	0.199 (9)
C27R	0.411 (3)	0.0077 (11)	0.850 (5)	0.085 (15)*	0.199 (9)
H27R	0.4311	−0.0196	0.9126	0.102*	0.199 (9)
N1P	0.6504 (8)	0.0136 (4)	0.5769 (13)	0.065 (3)	0.801 (9)
H1NP	0.7061	−0.0047	0.5431	0.098*	0.801 (9)
H2NP	0.6592	0.0234	0.7057	0.098*	0.801 (9)
H3NP	0.6490	0.0375	0.4919	0.098*	0.801 (9)
C20P	0.5443 (9)	−0.0121 (4)	0.560 (2)	0.072 (4)	0.801 (9)
H20P	0.5480	−0.0381	0.6549	0.086*	0.801 (9)
C21P	0.5317 (13)	−0.0308 (5)	0.344 (2)	0.096 (4)	0.801 (9)
H21D	0.5932	−0.0502	0.3127	0.143*	0.801 (9)
H21E	0.5293	−0.0059	0.2480	0.143*	0.801 (9)
H21F	0.4647	−0.0481	0.3353	0.143*	0.801 (9)
C22P	0.4528 (8)	0.0180 (3)	0.6289 (18)	0.077 (3)	0.801 (9)
C23P	0.4195 (9)	0.0548 (4)	0.510 (2)	0.105 (4)	0.801 (9)
H23P	0.4545	0.0605	0.3853	0.127*	0.801 (9)
C24P	0.3362 (10)	0.0829 (4)	0.574 (3)	0.133 (5)	0.801 (9)
H24P	0.3145	0.1076	0.4932	0.160*	0.801 (9)
C25P	0.2844 (10)	0.0741 (4)	0.759 (2)	0.136 (6)	0.801 (9)
H25P	0.2289	0.0935	0.8050	0.163*	0.801 (9)
C26P	0.3134 (11)	0.0376 (6)	0.875 (2)	0.140 (6)	0.801 (9)
H26P	0.2760	0.0313	0.9969	0.168*	0.801 (9)
C27P	0.4000 (12)	0.0095 (5)	0.8109 (19)	0.119 (6)	0.801 (9)
H27P	0.4218	−0.0150	0.8923	0.142*	0.801 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1P	0.132 (6)	0.079 (4)	0.153 (6)	0.000 (4)	−0.066 (6)	−0.011 (4)
C1P	0.108 (8)	0.065 (5)	0.085 (7)	0.018 (4)	−0.028 (5)	0.009 (4)
C2P	0.134 (7)	0.062 (4)	0.077 (5)	0.030 (5)	0.009 (5)	0.013 (4)
C3P	0.084 (6)	0.082 (6)	0.159 (10)	0.003 (5)	0.022 (6)	0.024 (6)
C4P	0.109 (9)	0.068 (5)	0.144 (9)	−0.012 (5)	−0.055 (7)	0.004 (7)
C5P	0.145 (10)	0.068 (5)	0.075 (6)	0.009 (6)	−0.018 (5)	0.015 (4)
C6P	0.211 (14)	0.073 (6)	0.126 (9)	0.017 (8)	−0.004 (10)	−0.024 (7)
C7P	0.148 (10)	0.061 (5)	0.163 (10)	0.019 (6)	0.001 (10)	0.050 (6)
C8P	0.114 (9)	0.137 (11)	0.176 (13)	−0.010 (8)	0.010 (9)	0.074 (10)
C9P	0.145 (10)	0.076 (6)	0.115 (8)	0.035 (6)	−0.003 (7)	0.022 (5)
C10P	0.081 (6)	0.075 (5)	0.102 (7)	0.015 (4)	0.019 (5)	0.002 (5)
C11P	0.090 (7)	0.064 (5)	0.090 (6)	0.006 (5)	−0.020 (4)	0.001 (4)
C12P	0.084 (6)	0.043 (3)	0.055 (4)	0.004 (3)	−0.001 (3)	0.009 (3)
C13P	0.106 (9)	0.054 (4)	0.050 (4)	0.015 (4)	0.009 (3)	0.014 (3)
C14P	0.096 (6)	0.054 (4)	0.058 (4)	0.021 (4)	0.011 (3)	0.005 (3)
C15P	0.075 (5)	0.046 (4)	0.046 (3)	0.017 (3)	0.005 (3)	0.006 (3)
C16P	0.104 (6)	0.057 (4)	0.053 (4)	0.018 (4)	0.027 (3)	0.008 (3)
C17P	0.084 (6)	0.040 (4)	0.110 (8)	0.010 (4)	0.021 (4)	−0.003 (4)
C18P	0.076 (5)	0.037 (3)	0.048 (4)	0.002 (3)	−0.004 (3)	0.006 (2)
C19P	0.107 (8)	0.140 (10)	0.193 (12)	0.044 (7)	0.053 (8)	0.069 (10)
O2P	0.097 (6)	0.074 (4)	0.056 (3)	0.018 (4)	0.009 (3)	0.014 (2)
O3P	0.087 (6)	0.061 (3)	0.068 (4)	0.024 (4)	0.003 (4)	−0.002 (3)
N1P	0.087 (6)	0.067 (4)	0.041 (4)	0.018 (3)	−0.001 (3)	0.005 (4)
C20P	0.079 (6)	0.051 (5)	0.086 (8)	0.005 (4)	−0.003 (4)	0.007 (4)
C21P	0.117 (9)	0.080 (7)	0.090 (7)	−0.020 (6)	−0.016 (7)	−0.002 (6)
C22P	0.072 (6)	0.072 (6)	0.087 (6)	−0.008 (4)	−0.001 (5)	0.008 (5)
C23P	0.098 (7)	0.085 (7)	0.134 (10)	0.014 (5)	0.022 (8)	0.026 (7)
C24P	0.092 (8)	0.094 (7)	0.215 (18)	0.019 (6)	0.031 (10)	0.016 (10)
C25P	0.083 (7)	0.109 (9)	0.216 (18)	0.017 (6)	0.012 (11)	−0.053 (11)
C26P	0.104 (9)	0.189 (17)	0.127 (10)	0.027 (9)	0.015 (9)	−0.004 (11)
C27P	0.102 (8)	0.156 (12)	0.098 (7)	0.027 (7)	0.000 (7)	−0.003 (7)

Geometric parameters (Å, º)

O1R—C11R	1.253 (15)	C5P—C6P	1.547 (9)
C1R—C9R	1.509 (19)	C6P—C7P	1.560 (13)
C1R—C2R	1.519 (19)	C7P—C9P	1.480 (13)
C1R—C10R	1.545 (18)	C7P—C8P	1.538 (13)
C2R—C3R	1.516 (19)	C10P—C19P	1.477 (11)
C3R—C4R	1.531 (10)	C10P—C11P	1.550 (10)
C3R—C8R	1.538 (18)	C11P—C12P	1.525 (7)
C4R—C5R	1.499 (10)	C12P—C13P	1.373 (7)
C5R—C10R	1.535 (18)	C12P—C17P	1.374 (7)
C5R—C6R	1.544 (19)	C13P—C14P	1.391 (6)
C6R—C7R	1.509 (19)	C14P—C15P	1.391 (6)
C7R—C8R	1.485 (19)	C15P—C16P	1.389 (6)
C7R—C9R	1.496 (19)	C15P—C18P	1.487 (7)
C10R—C11R	1.523 (16)	C16P—C17P	1.381 (7)
C10R—C19R	1.541 (19)	C18P—O2P	1.260 (6)
C11R—C12R	1.499 (14)	C18P—O3P	1.274 (7)
C12R—C17R	1.367 (14)	N1R—C20R	1.477 (19)
C12R—C13R	1.386 (15)	C20R—C22R	1.499 (15)
C13R—C14R	1.364 (14)	C20R—C21R	1.53 (2)
C14R—C15R	1.389 (14)	C22R—C23R	1.373 (9)
C15R—C16R	1.369 (15)	C22R—C27R	1.386 (9)
C15R—C18R	1.503 (13)	C23R—C24R	1.401 (9)
C16R—C17R	1.400 (14)	C24R—C25R	1.328 (9)
C18R—O2R	1.254 (10)	C25R—C26R	1.362 (9)
C18R—O3R	1.266 (10)	C26R—C27R	1.364 (9)
O1P—C11P	1.465 (5)	N1P—C20P	1.496 (11)
C1P—C9P	1.502 (12)	C20P—C22P	1.488 (8)
C1P—C2P	1.533 (5)	C20P—C21P	1.511 (13)
C1P—C10P	1.557 (10)	C22P—C27P	1.367 (7)
C2P—C3P	1.484 (11)	C22P—C23P	1.384 (7)
C2P—C11P	1.509 (10)	C23P—C24P	1.368 (7)
C3P—C4P	1.497 (9)	C24P—C25P	1.383 (8)
C3P—C8P	1.506 (12)	C25P—C26P	1.351 (8)
C4P—C5P	1.518 (9)	C26P—C27P	1.399 (8)
C5P—C10P	1.544 (8)
C9R—C1R—C2R	109 (2)	C9P—C7P—C8P	104.8 (9)
C9R—C1R—C10R	109 (2)	C9P—C7P—C6P	108.2 (10)
C2R—C1R—C10R	110.1 (19)	C8P—C7P—C6P	112.3 (9)
C3R—C2R—C1R	110.8 (18)	C3P—C8P—C7P	111.2 (8)
C2R—C3R—C4R	106 (2)	C7P—C9P—C1P	108.0 (7)
C2R—C3R—C8R	109.4 (19)	C19P—C10P—C5P	112.6 (9)
C4R—C3R—C8R	108 (2)	C19P—C10P—C11P	121.3 (8)
C5R—C4R—C3R	112.3 (19)	C5P—C10P—C11P	109.0 (7)
C4R—C5R—C10R	106 (2)	C19P—C10P—C1P	118.0 (9)
C4R—C5R—C6R	112 (2)	C5P—C10P—C1P	108.1 (7)
C10R—C5R—C6R	108 (2)	C11P—C10P—C1P	84.6 (5)
C7R—C6R—C5R	110 (2)	O1P—C11P—C2P	106.2 (6)
C8R—C7R—C9R	113 (2)	O1P—C11P—C12P	102.7 (4)
C8R—C7R—C6R	108 (2)	C2P—C11P—C12P	125.2 (6)
C9R—C7R—C6R	108 (2)	O1P—C11P—C10P	109.3 (6)
C7R—C8R—C3R	110.8 (18)	C2P—C11P—C10P	85.8 (4)
C7R—C9R—C1R	110.8 (19)	C12P—C11P—C10P	126.0 (6)
C11R—C10R—C5R	112.6 (19)	C13P—C12P—C17P	118.5 (5)
C11R—C10R—C19R	103 (2)	C13P—C12P—C11P	119.1 (5)
C5R—C10R—C19R	111 (2)	C17P—C12P—C11P	122.3 (6)
C11R—C10R—C1R	108.9 (16)	C12P—C13P—C14P	120.5 (5)
C5R—C10R—C1R	109.0 (17)	C13P—C14P—C15P	120.9 (5)
C19R—C10R—C1R	112 (2)	C16P—C15P—C14P	118.0 (5)
O1R—C11R—C12R	115.4 (13)	C16P—C15P—C18P	121.1 (5)
O1R—C11R—C10R	116.6 (12)	C14P—C15P—C18P	120.9 (5)
C12R—C11R—C10R	127.7 (14)	C17P—C16P—C15P	120.2 (5)
C17R—C12R—C13R	119.5 (9)	C12P—C17P—C16P	121.7 (5)
C17R—C12R—C11R	125.6 (14)	O2P—C18P—O3P	122.3 (6)
C13R—C12R—C11R	114.9 (15)	O2P—C18P—C15P	118.3 (6)
C14R—C13R—C12R	120.7 (10)	O3P—C18P—C15P	119.2 (5)
C13R—C14R—C15R	120.7 (10)	N1R—C20R—C22R	116 (2)
C16R—C15R—C14R	118.5 (9)	N1R—C20R—C21R	109 (3)
C16R—C15R—C18R	122.9 (14)	C22R—C20R—C21R	111 (3)
C14R—C15R—C18R	118.5 (12)	C23R—C22R—C27R	117.6 (7)
C15R—C16R—C17R	121.1 (10)	C23R—C22R—C20R	122.8 (13)
C12R—C17R—C16R	119.5 (10)	C27R—C22R—C20R	119.7 (12)
O2R—C18R—O3R	123.3 (14)	C22R—C23R—C24R	120.5 (8)
O2R—C18R—C15R	117.5 (12)	C25R—C24R—C23R	119.5 (8)
O3R—C18R—C15R	116.4 (11)	C24R—C25R—C26R	121.7 (8)
C9P—C1P—C2P	121.4 (9)	C25R—C26R—C27R	119.2 (8)
C9P—C1P—C10P	119.4 (9)	C26R—C27R—C22R	121.5 (8)
C2P—C1P—C10P	84.7 (4)	C22P—C20P—N1P	108.8 (9)
C3P—C2P—C11P	113.5 (6)	C22P—C20P—C21P	114.6 (10)
C3P—C2P—C1P	110.2 (7)	N1P—C20P—C21P	109.7 (8)
C11P—C2P—C1P	86.9 (6)	C27P—C22P—C23P	119.1 (6)
C2P—C3P—C4P	110.0 (7)	C27P—C22P—C20P	120.1 (6)
C2P—C3P—C8P	109.9 (8)	C23P—C22P—C20P	120.8 (6)
C4P—C3P—C8P	110.0 (11)	C24P—C23P—C22P	121.0 (6)
C3P—C4P—C5P	104.2 (8)	C23P—C24P—C25P	119.1 (6)
C4P—C5P—C10P	111.1 (7)	C26P—C25P—C24P	121.0 (6)
C4P—C5P—C6P	105.6 (9)	C25P—C26P—C27P	119.6 (7)
C10P—C5P—C6P	112.3 (8)	C22P—C27P—C26P	120.2 (7)
C5P—C6P—C7P	109.5 (7)

(87.5P)

Crystal data

C27H33NO3	Dx = 1.205 Mg m^−3
Mr = 419.54	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1451 reflections
a = 12.364 (3) Å	θ = 6–19°
b = 28.956 (6) Å	µ = 0.08 mm^−1
c = 6.4582 (11) Å	T = 293 K
V = 2312.1 (8) Å^3	Block, colourless
Z = 4	0.56 × 0.41 × 0.20 mm
F(000) = 904

Data collection

Kuma KM4CCD diffractometer	3001 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.078
Graphite monochromator	θmax = 25.0°, θmin = 6.0°
ω scans	h = −13→14
10478 measured reflections	k = −34→34
3996 independent reflections	l = −6→7

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.088	w = 1/[σ^2(Fo^2) + (0.0849P)^2 + 1.6461P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.230	(Δ/σ)max = 0.002
S = 1.11	Δρmax = 0.24 e Å^−3
3996 reflections	Δρmin = −0.21 e Å^−3
406 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
282 restraints	Extinction coefficient: 0.093 (13)
Primary atom site location: structure-invariant direct methods	Absolute structure: The absolute configuration was assigned to agree with that from Leibovitch M. et all, 1997; 1998
Secondary atom site location: inferred from neighbouring sites

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1R	0.424 (5)	0.2175 (15)	0.458 (5)	0.16 (2)*	0.125 (7)
C1R	0.399 (3)	0.3063 (11)	0.542 (6)	0.11 (4)*	0.125 (7)
H1R	0.3471	0.2938	0.4419	0.133*	0.125 (7)
C2R	0.508 (3)	0.3124 (16)	0.441 (5)	0.111 (15)*	0.125 (7)
H2AR	0.5007	0.3329	0.3228	0.133*	0.125 (7)
H2BR	0.5334	0.2828	0.3913	0.133*	0.125 (7)
C3R	0.589 (3)	0.3325 (13)	0.594 (5)	0.071 (17)*	0.125 (7)
H3R	0.6597	0.3371	0.5274	0.085*	0.125 (7)
C4R	0.598 (3)	0.2973 (14)	0.770 (7)	0.08 (2)*	0.125 (7)
H4AR	0.6182	0.2674	0.7142	0.094*	0.125 (7)
H4BR	0.6539	0.3069	0.8666	0.094*	0.125 (7)
C5R	0.492 (3)	0.2934 (13)	0.882 (5)	0.08 (2)*	0.125 (7)
H5R	0.4997	0.2726	1.0002	0.100*	0.125 (7)
C6R	0.450 (4)	0.3406 (15)	0.956 (6)	0.15 (2)*	0.125 (7)
H6AR	0.3811	0.3367	1.0262	0.178*	0.125 (7)
H6BR	0.5008	0.3539	1.0538	0.178*	0.125 (7)
C7R	0.436 (3)	0.3723 (13)	0.774 (7)	0.106 (16)*	0.125 (7)
H7R	0.4093	0.4023	0.8220	0.128*	0.125 (7)
C8R	0.544 (3)	0.3788 (12)	0.674 (7)	0.11 (2)*	0.125 (7)
H8AR	0.5940	0.3920	0.7732	0.132*	0.125 (7)
H8BR	0.5370	0.4002	0.5592	0.132*	0.125 (7)
C9R	0.358 (3)	0.3520 (13)	0.623 (7)	0.105 (19)*	0.125 (7)
H9AR	0.3473	0.3732	0.5084	0.126*	0.125 (7)
H9BR	0.2884	0.3475	0.6906	0.126*	0.125 (7)
C10R	0.410 (2)	0.2727 (9)	0.726 (5)	0.046 (11)*	0.125 (7)
C11R	0.454 (4)	0.2277 (10)	0.635 (5)	0.057 (6)*	0.125 (7)
C12R	0.508 (3)	0.1905 (9)	0.758 (5)	0.036 (11)*	0.125 (7)
C13R	0.586 (3)	0.1658 (13)	0.654 (5)	0.039 (11)*	0.125 (7)
H13R	0.6006	0.1728	0.5162	0.047*	0.125 (7)
C14R	0.641 (3)	0.1308 (14)	0.749 (4)	0.048 (5)*	0.125 (7)
H14R	0.6938	0.1144	0.6761	0.057*	0.125 (7)
C15R	0.620 (3)	0.1197 (11)	0.954 (4)	0.043 (6)*	0.125 (7)
C16R	0.543 (3)	0.1442 (15)	1.058 (5)	0.054 (6)*	0.125 (7)
H16R	0.5280	0.1369	1.1950	0.064*	0.125 (7)
C17R	0.485 (4)	0.1799 (16)	0.962 (6)	0.07 (2)*	0.125 (7)
H17R	0.4329	0.1962	1.0344	0.082*	0.125 (7)
C18R	0.681 (3)	0.0810 (11)	1.054 (4)	0.030 (12)*	0.125 (7)
C19R	0.302 (3)	0.258 (2)	0.818 (9)	0.14 (2)*	0.125 (7)
H19A	0.2659	0.2842	0.8749	0.215*	0.125 (7)
H19B	0.3150	0.2356	0.9262	0.215*	0.125 (7)
H19C	0.2585	0.2441	0.7122	0.215*	0.125 (7)
O2R	0.684 (4)	0.0794 (15)	1.247 (4)	0.058 (13)*	0.125 (7)
O3R	0.719 (4)	0.0502 (14)	0.937 (5)	0.053 (13)*	0.125 (7)
O1P	0.3518 (5)	0.20725 (15)	0.5421 (10)	0.0985 (19)	0.875 (7)
HO1P	0.3820	0.1893	0.4628	0.148*	0.875 (7)
C1P	0.3849 (7)	0.2954 (3)	0.5320 (11)	0.073 (3)	0.875 (7)
H1P	0.3253	0.2822	0.4516	0.087*	0.875 (7)
C2P	0.4852 (5)	0.26558 (16)	0.5063 (8)	0.0707 (17)	0.875 (7)
H2P	0.4948	0.2528	0.3670	0.085*	0.875 (7)
C3P	0.5831 (5)	0.2896 (2)	0.5917 (12)	0.086 (2)	0.875 (7)
H3P	0.6486	0.2746	0.5397	0.103*	0.875 (7)
C4P	0.5805 (6)	0.2868 (3)	0.8247 (13)	0.085 (2)	0.875 (7)
H4AP	0.6350	0.3067	0.8850	0.102*	0.875 (7)
H4BP	0.5934	0.2553	0.8706	0.102*	0.875 (7)
C5P	0.4669 (7)	0.3027 (2)	0.8861 (10)	0.078 (2)	0.875 (7)
H5P	0.4551	0.2968	1.0338	0.093*	0.875 (7)
C6P	0.4651 (8)	0.3556 (2)	0.8447 (12)	0.103 (3)	0.875 (7)
H6AP	0.3959	0.3683	0.8868	0.124*	0.875 (7)
H6BP	0.5213	0.3706	0.9251	0.124*	0.875 (7)
C7P	0.4834 (7)	0.3647 (2)	0.6142 (12)	0.091 (2)	0.875 (7)
H7P	0.4897	0.3980	0.5911	0.109*	0.875 (7)
C8P	0.5834 (7)	0.3406 (3)	0.5280 (19)	0.116 (4)	0.875 (7)
H8AP	0.6481	0.3555	0.5807	0.140*	0.875 (7)
H8BP	0.5840	0.3430	0.3782	0.140*	0.875 (7)
C9P	0.3891 (6)	0.3467 (2)	0.4965 (12)	0.086 (2)	0.875 (7)
H9AP	0.3974	0.3533	0.3501	0.103*	0.875 (7)
H9BP	0.3229	0.3612	0.5447	0.103*	0.875 (7)
C10P	0.3812 (5)	0.2762 (2)	0.7567 (11)	0.0679 (19)	0.875 (7)
C11P	0.4326 (5)	0.2324 (2)	0.6607 (10)	0.0615 (16)	0.875 (7)
C12P	0.4918 (6)	0.19498 (18)	0.7761 (10)	0.057 (2)	0.875 (7)
C13P	0.5717 (7)	0.1704 (3)	0.6759 (10)	0.065 (2)	0.875 (7)
H13P	0.5929	0.1792	0.5436	0.077*	0.875 (7)
C14P	0.6211 (6)	0.1326 (2)	0.7691 (8)	0.0559 (15)	0.875 (7)
H14P	0.6722	0.1156	0.6960	0.067*	0.875 (7)
C15P	0.5949 (5)	0.12010 (18)	0.9701 (8)	0.0441 (12)	0.875 (7)
C16P	0.5170 (6)	0.1459 (2)	1.0733 (9)	0.0605 (16)	0.875 (7)
H16P	0.4988	0.1385	1.2091	0.073*	0.875 (7)
C17P	0.4664 (8)	0.1823 (2)	0.9762 (10)	0.060 (3)	0.875 (7)
H17P	0.4137	0.1988	1.0474	0.072*	0.875 (7)
C18P	0.6497 (6)	0.08072 (18)	1.0729 (8)	0.0467 (15)	0.875 (7)
C19P	0.2744 (6)	0.2733 (3)	0.8635 (15)	0.107 (3)	0.875 (7)
H19D	0.2837	0.2594	0.9972	0.160*	0.875 (7)
H19E	0.2257	0.2549	0.7822	0.160*	0.875 (7)
H19F	0.2451	0.3038	0.8799	0.160*	0.875 (7)
O2P	0.6506 (7)	0.0792 (2)	1.2671 (7)	0.073 (2)	0.875 (7)
O3P	0.6932 (7)	0.0495 (2)	0.9609 (9)	0.067 (2)	0.875 (7)
N1R	0.652 (3)	0.0181 (16)	0.525 (6)	0.034 (11)*	0.125 (7)
H1NR	0.7025	0.0005	0.4661	0.051*	0.125 (7)
H2NR	0.6793	0.0311	0.6387	0.051*	0.125 (7)
H3NR	0.6319	0.0401	0.4366	0.051*	0.125 (7)
C20R	0.558 (4)	−0.0103 (15)	0.580 (8)	0.05 (2)*	0.125 (7)
H20R	0.5813	−0.0328	0.6851	0.057*	0.125 (7)
C21R	0.521 (6)	−0.037 (3)	0.390 (15)	0.13 (6)*	0.125 (7)
H21A	0.5801	−0.0550	0.3366	0.188*	0.125 (7)
H21B	0.4968	−0.0158	0.2855	0.188*	0.125 (7)
H21C	0.4626	−0.0573	0.4269	0.188*	0.125 (7)
C22R	0.468 (3)	0.0177 (12)	0.671 (6)	0.051 (17)*	0.125 (7)
C23R	0.431 (4)	0.0579 (16)	0.583 (6)	0.077 (11)*	0.125 (7)
H23R	0.4629	0.0687	0.4613	0.092*	0.125 (7)
C24R	0.347 (4)	0.0828 (17)	0.674 (7)	0.102 (12)*	0.125 (7)
H24R	0.3226	0.1102	0.6148	0.122*	0.125 (7)
C25R	0.301 (4)	0.0672 (18)	0.847 (7)	0.091 (17)*	0.125 (7)
H25R	0.2453	0.0840	0.9072	0.109*	0.125 (7)
C26R	0.334 (4)	0.0271 (18)	0.937 (7)	0.09 (2)*	0.125 (7)
H26R	0.2994	0.0160	1.0551	0.108*	0.125 (7)
C27R	0.419 (3)	0.0035 (14)	0.853 (6)	0.053 (12)*	0.125 (7)
H27R	0.4442	−0.0229	0.9199	0.063*	0.125 (7)
N1P	0.6509 (5)	0.0127 (2)	0.5729 (10)	0.0535 (18)	0.875 (7)
H1NP	0.7052	−0.0060	0.5388	0.080*	0.875 (7)
H2NP	0.6600	0.0227	0.7020	0.080*	0.875 (7)
H3NP	0.6496	0.0367	0.4868	0.080*	0.875 (7)
C20P	0.5463 (7)	−0.0131 (3)	0.5578 (16)	0.063 (3)	0.875 (7)
H20P	0.5503	−0.0392	0.6539	0.076*	0.875 (7)
C21P	0.5346 (9)	−0.0324 (4)	0.343 (2)	0.086 (3)	0.875 (7)
H21D	0.5957	−0.0517	0.3124	0.129*	0.875 (7)
H21E	0.5311	−0.0075	0.2454	0.129*	0.875 (7)
H21F	0.4695	−0.0504	0.3353	0.129*	0.875 (7)
C22P	0.4549 (6)	0.0171 (2)	0.6266 (15)	0.068 (2)	0.875 (7)
C23P	0.4215 (7)	0.0541 (3)	0.5080 (15)	0.102 (3)	0.875 (7)
H23P	0.4560	0.0602	0.3830	0.123*	0.875 (7)
C24P	0.3380 (7)	0.0820 (3)	0.5713 (18)	0.126 (4)	0.875 (7)
H24P	0.3165	0.1071	0.4909	0.152*	0.875 (7)
C25P	0.2865 (7)	0.0725 (3)	0.7557 (18)	0.125 (4)	0.875 (7)
H25P	0.2309	0.0917	0.8009	0.150*	0.875 (7)
C26P	0.3155 (8)	0.0357 (4)	0.8720 (15)	0.124 (4)	0.875 (7)
H26P	0.2791	0.0291	0.9943	0.149*	0.875 (7)
C27P	0.4011 (7)	0.0078 (3)	0.8060 (13)	0.094 (3)	0.875 (7)
H27P	0.4216	−0.0175	0.8856	0.113*	0.875 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1P	0.100 (4)	0.064 (3)	0.132 (4)	−0.002 (2)	−0.058 (3)	−0.004 (3)
C1P	0.079 (5)	0.058 (3)	0.081 (5)	0.010 (3)	−0.018 (4)	0.007 (3)
C2P	0.102 (5)	0.050 (3)	0.060 (3)	0.017 (3)	0.004 (3)	0.010 (2)
C3P	0.078 (4)	0.062 (4)	0.119 (6)	0.009 (3)	0.020 (4)	0.029 (4)
C4P	0.071 (5)	0.058 (4)	0.127 (6)	−0.012 (3)	−0.032 (4)	0.016 (5)
C5P	0.110 (6)	0.058 (4)	0.064 (4)	0.014 (4)	−0.008 (4)	0.004 (3)
C6P	0.163 (8)	0.051 (3)	0.095 (5)	0.017 (4)	−0.019 (6)	−0.003 (4)
C7P	0.113 (6)	0.042 (3)	0.117 (6)	0.005 (4)	0.003 (5)	0.021 (3)
C8P	0.109 (7)	0.088 (6)	0.152 (9)	−0.015 (5)	−0.003 (6)	0.053 (6)
C9P	0.110 (5)	0.060 (3)	0.089 (5)	0.024 (4)	−0.006 (4)	0.016 (3)
C10P	0.049 (3)	0.069 (4)	0.086 (4)	0.009 (3)	0.016 (3)	0.009 (3)
C11P	0.061 (4)	0.055 (3)	0.069 (3)	0.012 (3)	−0.002 (3)	0.004 (3)
C12P	0.060 (4)	0.047 (3)	0.063 (4)	0.014 (3)	0.003 (3)	0.004 (2)
C13P	0.093 (6)	0.051 (3)	0.050 (3)	0.020 (3)	0.011 (3)	0.013 (3)
C14P	0.071 (4)	0.047 (2)	0.049 (3)	0.020 (3)	0.013 (2)	0.007 (2)
C15P	0.048 (3)	0.038 (2)	0.046 (2)	0.009 (2)	0.006 (2)	0.0049 (19)
C16P	0.077 (5)	0.051 (3)	0.054 (3)	0.012 (3)	0.023 (3)	0.008 (2)
C17P	0.063 (4)	0.045 (3)	0.072 (5)	0.013 (3)	0.015 (3)	0.002 (2)
C18P	0.047 (4)	0.041 (3)	0.052 (3)	−0.002 (2)	0.004 (3)	0.003 (2)
C19P	0.074 (4)	0.097 (5)	0.150 (7)	0.030 (4)	0.034 (5)	0.030 (5)
O2P	0.110 (6)	0.060 (3)	0.049 (2)	0.021 (3)	0.004 (3)	0.0094 (18)
O3P	0.081 (5)	0.062 (3)	0.056 (3)	0.033 (3)	−0.002 (3)	−0.002 (2)
N1P	0.067 (4)	0.053 (3)	0.041 (3)	0.014 (2)	−0.004 (2)	0.008 (3)
C20P	0.066 (5)	0.051 (4)	0.072 (5)	0.000 (3)	−0.004 (3)	0.006 (3)
C21P	0.103 (7)	0.071 (5)	0.085 (5)	−0.009 (4)	−0.020 (5)	−0.015 (5)
C22P	0.056 (4)	0.064 (4)	0.084 (5)	−0.005 (3)	−0.002 (4)	0.007 (3)
C23P	0.087 (5)	0.071 (4)	0.149 (8)	0.024 (4)	0.027 (6)	0.048 (5)
C24P	0.088 (5)	0.074 (4)	0.217 (12)	0.026 (4)	0.044 (7)	0.035 (6)
C25P	0.071 (5)	0.098 (6)	0.206 (12)	0.021 (5)	0.017 (8)	−0.033 (8)
C26P	0.092 (6)	0.166 (11)	0.114 (7)	0.035 (7)	0.017 (6)	−0.003 (8)
C27P	0.077 (5)	0.123 (7)	0.082 (5)	0.024 (5)	0.000 (5)	0.006 (5)

Geometric parameters (Å, º)

O1R—C11R	1.239 (17)	C5P—C6P	1.555 (8)
C1R—C2R	1.51 (2)	C6P—C7P	1.529 (10)
C1R—C9R	1.51 (2)	C7P—C9P	1.485 (10)
C1R—C10R	1.541 (19)	C7P—C8P	1.525 (10)
C2R—C3R	1.53 (2)	C10P—C19P	1.493 (9)
C3R—C4R	1.531 (11)	C10P—C11P	1.548 (7)
C3R—C8R	1.54 (2)	C11P—C12P	1.506 (6)
C4R—C5R	1.501 (11)	C12P—C13P	1.379 (7)
C5R—C6R	1.540 (19)	C12P—C17P	1.379 (6)
C5R—C10R	1.544 (19)	C13P—C14P	1.390 (6)
C6R—C7R	1.50 (2)	C14P—C15P	1.386 (5)
C7R—C8R	1.49 (2)	C15P—C16P	1.390 (6)
C7R—C9R	1.50 (2)	C15P—C18P	1.483 (6)
C10R—C19R	1.520 (18)	C16P—C17P	1.376 (6)
C10R—C11R	1.529 (17)	C18P—O2P	1.255 (5)
C11R—C12R	1.499 (16)	C18P—O3P	1.276 (6)
C12R—C13R	1.374 (16)	N1R—C20R	1.47 (2)
C12R—C17R	1.381 (16)	C20R—C22R	1.498 (11)
C13R—C14R	1.372 (14)	C20R—C21R	1.53 (2)
C14R—C15R	1.384 (15)	C22R—C23R	1.373 (9)
C15R—C16R	1.367 (15)	C22R—C27R	1.388 (9)
C15R—C18R	1.496 (11)	C23R—C24R	1.403 (9)
C16R—C17R	1.398 (14)	C24R—C25R	1.327 (9)
C18R—O2R	1.250 (9)	C25R—C26R	1.363 (9)
C18R—O3R	1.262 (9)	C26R—C27R	1.363 (9)
O1P—C11P	1.454 (8)	N1P—C20P	1.495 (9)
C1P—C9P	1.504 (10)	C20P—C22P	1.497 (7)
C1P—C2P	1.521 (8)	C20P—C21P	1.500 (11)
C1P—C10P	1.555 (8)	C22P—C27P	1.363 (7)
C2P—C3P	1.502 (9)	C22P—C23P	1.380 (7)
C2P—C11P	1.529 (7)	C23P—C24P	1.373 (7)
C3P—C4P	1.507 (8)	C24P—C25P	1.379 (8)
C3P—C8P	1.532 (9)	C25P—C26P	1.352 (8)
C4P—C5P	1.531 (8)	C26P—C27P	1.398 (7)
C5P—C10P	1.552 (7)
C2R—C1R—C9R	110 (2)	C9P—C7P—C8P	106.8 (6)
C2R—C1R—C10R	109 (2)	C9P—C7P—C6P	108.8 (7)
C9R—C1R—C10R	109 (2)	C8P—C7P—C6P	113.4 (7)
C1R—C2R—C3R	111 (2)	C7P—C8P—C3P	109.9 (6)
C2R—C3R—C4R	106 (2)	C7P—C9P—C1P	107.1 (5)
C2R—C3R—C8R	108 (2)	C19P—C10P—C11P	120.1 (6)
C4R—C3R—C8R	111 (2)	C19P—C10P—C5P	112.5 (6)
C5R—C4R—C3R	110 (2)	C11P—C10P—C5P	109.9 (5)
C4R—C5R—C6R	112 (2)	C19P—C10P—C1P	118.5 (6)
C4R—C5R—C10R	107 (2)	C11P—C10P—C1P	84.7 (5)
C6R—C5R—C10R	109 (2)	C5P—C10P—C1P	107.8 (6)
C7R—C6R—C5R	110 (2)	O1P—C11P—C12P	103.5 (4)
C8R—C7R—C9R	110 (2)	O1P—C11P—C2P	105.3 (5)
C8R—C7R—C6R	108 (2)	C12P—C11P—C2P	124.6 (5)
C9R—C7R—C6R	110 (2)	O1P—C11P—C10P	109.9 (5)
C7R—C8R—C3R	111 (2)	C12P—C11P—C10P	126.2 (5)
C7R—C9R—C1R	111 (2)	C2P—C11P—C10P	85.5 (4)
C19R—C10R—C11R	102 (2)	C13P—C12P—C17P	117.7 (4)
C19R—C10R—C1R	113.7 (15)	C13P—C12P—C11P	119.2 (5)
C11R—C10R—C1R	105.9 (19)	C17P—C12P—C11P	123.0 (6)
C19R—C10R—C5R	115 (2)	C12P—C13P—C14P	121.2 (4)
C11R—C10R—C5R	111 (2)	C15P—C14P—C13P	120.6 (4)
C1R—C10R—C5R	108.4 (18)	C14P—C15P—C16P	118.1 (4)
O1R—C11R—C12R	116.9 (14)	C14P—C15P—C18P	120.9 (4)
O1R—C11R—C10R	117.1 (15)	C16P—C15P—C18P	121.0 (4)
C12R—C11R—C10R	124.5 (18)	C17P—C16P—C15P	120.5 (5)
C13R—C12R—C17R	119.6 (9)	C16P—C17P—C12P	121.9 (6)
C13R—C12R—C11R	115.4 (19)	O2P—C18P—O3P	122.6 (5)
C17R—C12R—C11R	125 (2)	O2P—C18P—C15P	118.6 (5)
C14R—C13R—C12R	121.1 (11)	O3P—C18P—C15P	118.9 (4)
C13R—C14R—C15R	120.2 (11)	N1R—C20R—C22R	112.4 (15)
C16R—C15R—C14R	118.8 (9)	N1R—C20R—C21R	109 (3)
C16R—C15R—C18R	121.8 (12)	C22R—C20R—C21R	111 (3)
C14R—C15R—C18R	119.3 (12)	C23R—C22R—C27R	117.3 (7)
C15R—C16R—C17R	121.4 (11)	C23R—C22R—C20R	122.9 (9)
C12R—C17R—C16R	118.9 (11)	C27R—C22R—C20R	119.8 (9)
O2R—C18R—O3R	124.1 (12)	C22R—C23R—C24R	120.5 (8)
O2R—C18R—C15R	118.4 (10)	C25R—C24R—C23R	119.7 (8)
O3R—C18R—C15R	117.3 (10)	C24R—C25R—C26R	121.6 (8)
C9P—C1P—C2P	121.1 (7)	C27R—C26R—C25R	119.1 (8)
C9P—C1P—C10P	119.8 (7)	C26R—C27R—C22R	121.7 (8)
C2P—C1P—C10P	85.5 (4)	N1P—C20P—C22P	110.0 (6)
C3P—C2P—C1P	110.7 (6)	N1P—C20P—C21P	109.2 (7)
C3P—C2P—C11P	113.3 (5)	C22P—C20P—C21P	114.8 (8)
C1P—C2P—C11P	86.5 (5)	C27P—C22P—C23P	118.7 (5)
C2P—C3P—C4P	108.9 (5)	C27P—C22P—C20P	120.3 (6)
C2P—C3P—C8P	110.5 (6)	C23P—C22P—C20P	121.0 (6)
C4P—C3P—C8P	108.7 (7)	C24P—C23P—C22P	121.1 (6)
C3P—C4P—C5P	105.1 (5)	C23P—C24P—C25P	119.2 (6)
C4P—C5P—C10P	109.7 (6)	C26P—C25P—C24P	120.9 (5)
C4P—C5P—C6P	105.4 (6)	C25P—C26P—C27P	119.2 (6)
C10P—C5P—C6P	112.6 (6)	C22P—C27P—C26P	120.9 (6)
C7P—C6P—C5P	109.6 (5)

(91.0P)

Crystal data

C27H33NO3	Dx = 1.208 Mg m^−3
Mr = 419.54	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1668 reflections
a = 12.4079 (16) Å	θ = 6–20°
b = 28.861 (3) Å	µ = 0.08 mm^−1
c = 6.4428 (7) Å	T = 293 K
V = 2307.2 (5) Å^3	Block, colourless
Z = 4	0.56 × 0.41 × 0.20 mm
F(000) = 904

Data collection

Kuma KM4CCD diffractometer	3180 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.069
Graphite monochromator	θmax = 25.0°, θmin = 6.0°
ω scans	h = −14→13
10868 measured reflections	k = −34→34
4013 independent reflections	l = −7→6

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.082	w = 1/[σ^2(Fo^2) + (0.0829P)^2 + 1.3126P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.205	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.24 e Å^−3
4013 reflections	Δρmin = −0.20 e Å^−3
406 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
336 restraints	Extinction coefficient: 0.065 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: The absolute configuration was assigned to agree with that from Leibovitch M. et all, 1997; 1998
Secondary atom site location: inferred from neighbouring sites

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1R	0.413 (6)	0.2244 (18)	0.433 (5)	0.15 (2)*	0.090 (6)
C1R	0.387 (4)	0.3088 (13)	0.528 (6)	0.056 (16)*	0.090 (6)
H1R	0.3405	0.2974	0.4154	0.067*	0.090 (6)
C2R	0.501 (4)	0.3122 (19)	0.450 (6)	0.119 (18)*	0.090 (6)
H2AR	0.5041	0.3332	0.3325	0.143*	0.090 (6)
H2BR	0.5258	0.2820	0.4045	0.143*	0.090 (6)
C3R	0.574 (3)	0.3301 (17)	0.623 (7)	0.098 (18)*	0.090 (6)
H3R	0.6496	0.3315	0.5760	0.118*	0.090 (6)
C4R	0.563 (4)	0.2970 (19)	0.807 (8)	0.074 (18)*	0.090 (6)
H4AR	0.5854	0.2663	0.7648	0.089*	0.090 (6)
H4BR	0.6103	0.3071	0.9176	0.089*	0.090 (6)
C5R	0.450 (4)	0.2941 (15)	0.891 (6)	0.09 (2)*	0.090 (6)
H5R	0.4471	0.2738	1.0127	0.112*	0.090 (6)
C6R	0.411 (5)	0.3436 (17)	0.947 (7)	0.14 (2)*	0.090 (6)
H6AR	0.3364	0.3425	0.9922	0.168*	0.090 (6)
H6BR	0.4541	0.3558	1.0598	0.168*	0.090 (6)
C7R	0.421 (4)	0.3747 (14)	0.761 (8)	0.115 (18)*	0.090 (6)
H7R	0.3952	0.4056	0.7999	0.138*	0.090 (6)
C8R	0.534 (4)	0.3786 (15)	0.687 (9)	0.113 (19)*	0.090 (6)
H8AR	0.5791	0.3910	0.7971	0.135*	0.090 (6)
H8BR	0.5374	0.3996	0.5698	0.135*	0.090 (6)
C9R	0.348 (4)	0.3560 (14)	0.595 (8)	0.11 (3)*	0.090 (6)
H9AR	0.3484	0.3769	0.4772	0.129*	0.090 (6)
H9BR	0.2753	0.3538	0.6473	0.129*	0.090 (6)
C10R	0.380 (3)	0.2749 (10)	0.715 (6)	0.08 (4)*	0.090 (6)
C11R	0.419 (4)	0.2288 (12)	0.625 (6)	0.053 (6)*	0.090 (6)
C12R	0.475 (3)	0.1913 (10)	0.742 (5)	0.064 (11)*	0.090 (6)
C13R	0.566 (4)	0.1723 (18)	0.649 (6)	0.044 (10)*	0.090 (6)
H13R	0.5881	0.1832	0.5205	0.053*	0.090 (6)
C14R	0.622 (4)	0.138 (2)	0.745 (7)	0.05 (3)*	0.090 (6)
H14R	0.6821	0.1250	0.6794	0.065*	0.090 (6)
C15R	0.592 (4)	0.1213 (15)	0.937 (6)	0.037 (10)*	0.090 (6)
C16R	0.500 (4)	0.1391 (14)	1.027 (6)	0.07 (3)*	0.090 (6)
H16R	0.4746	0.1265	1.1505	0.083*	0.090 (6)
C17R	0.444 (3)	0.1755 (14)	0.936 (5)	0.040 (13)*	0.090 (6)
H17R	0.3865	0.1892	1.0041	0.048*	0.090 (6)
C18R	0.654 (5)	0.0833 (19)	1.039 (6)	0.07 (2)*	0.090 (6)
C19R	0.263 (4)	0.265 (2)	0.777 (12)	0.16 (2)*	0.090 (6)
H19A	0.2303	0.2930	0.8294	0.236*	0.090 (6)
H19B	0.2612	0.2417	0.8832	0.236*	0.090 (6)
H19C	0.2231	0.2545	0.6583	0.236*	0.090 (6)
O2R	0.671 (3)	0.0858 (14)	1.230 (6)	0.034 (10)*	0.090 (6)
O3R	0.704 (6)	0.056 (2)	0.920 (7)	0.06 (2)*	0.090 (6)
O1P	0.3491 (4)	0.20683 (13)	0.5474 (8)	0.0931 (15)	0.910 (6)
HO1P	0.3769	0.1885	0.4663	0.140*	0.910 (6)
C1P	0.3833 (5)	0.2950 (2)	0.5317 (10)	0.0687 (17)	0.910 (6)
H1P	0.3230	0.2817	0.4538	0.082*	0.910 (6)
C2P	0.4838 (4)	0.26519 (14)	0.5029 (7)	0.0643 (14)	0.910 (6)
H2P	0.4925	0.2522	0.3634	0.077*	0.910 (6)
C3P	0.5820 (4)	0.28910 (18)	0.5869 (9)	0.0771 (16)	0.910 (6)
H3P	0.6468	0.2739	0.5328	0.093*	0.910 (6)
C4P	0.5825 (5)	0.2868 (2)	0.8202 (11)	0.081 (2)	0.910 (6)
H4AP	0.6377	0.3070	0.8771	0.098*	0.910 (6)
H4BP	0.5955	0.2554	0.8675	0.098*	0.910 (6)
C5P	0.4700 (5)	0.30323 (18)	0.8852 (8)	0.0721 (17)	0.910 (6)
H5P	0.4595	0.2976	1.0338	0.087*	0.910 (6)
C6P	0.4653 (6)	0.35605 (16)	0.8411 (10)	0.0865 (19)	0.910 (6)
H6AP	0.3958	0.3682	0.8831	0.104*	0.910 (6)
H6BP	0.5206	0.3718	0.9209	0.104*	0.910 (6)
C7P	0.4829 (5)	0.36501 (17)	0.6089 (9)	0.0840 (19)	0.910 (6)
H7P	0.4895	0.3984	0.5844	0.101*	0.910 (6)
C8P	0.5826 (5)	0.3402 (2)	0.5243 (13)	0.102 (2)	0.910 (6)
H8AP	0.6471	0.3550	0.5780	0.122*	0.910 (6)
H8BP	0.5839	0.3427	0.3741	0.122*	0.910 (6)
C9P	0.3890 (5)	0.34672 (16)	0.4937 (9)	0.0787 (17)	0.910 (6)
H9AP	0.3970	0.3529	0.3465	0.094*	0.910 (6)
H9BP	0.3234	0.3615	0.5416	0.094*	0.910 (6)
C10P	0.3830 (4)	0.27621 (17)	0.7580 (14)	0.062 (2)	0.910 (6)
C11P	0.4342 (5)	0.23216 (17)	0.6607 (8)	0.0584 (13)	0.910 (6)
C12P	0.4937 (4)	0.19483 (13)	0.7763 (7)	0.0488 (11)	0.910 (6)
C13P	0.5724 (6)	0.1697 (2)	0.6755 (9)	0.0583 (16)	0.910 (6)
H13P	0.5926	0.1782	0.5417	0.070*	0.910 (6)
C14P	0.6224 (6)	0.1320 (3)	0.7691 (10)	0.053 (2)	0.910 (6)
H14P	0.6725	0.1147	0.6952	0.063*	0.910 (6)
C15P	0.5977 (5)	0.12015 (18)	0.9723 (8)	0.0432 (12)	0.910 (6)
C16P	0.5207 (5)	0.14610 (17)	1.0756 (9)	0.0539 (13)	0.910 (6)
H16P	0.5032	0.1388	1.2122	0.065*	0.910 (6)
C17P	0.4695 (4)	0.18261 (17)	0.9783 (8)	0.0545 (13)	0.910 (6)
H17P	0.4176	0.1994	1.0504	0.065*	0.910 (6)
C18P	0.6528 (5)	0.08045 (16)	1.0745 (7)	0.0445 (13)	0.910 (6)
C19P	0.2766 (5)	0.2742 (3)	0.8677 (13)	0.097 (2)	0.910 (6)
H19D	0.2859	0.2602	1.0016	0.146*	0.910 (6)
H19E	0.2268	0.2561	0.7874	0.146*	0.910 (6)
H19F	0.2488	0.3051	0.8842	0.146*	0.910 (6)
O2P	0.6533 (5)	0.07875 (18)	1.2681 (7)	0.0735 (17)	0.910 (6)
O3P	0.6938 (6)	0.0492 (2)	0.9611 (9)	0.0622 (16)	0.910 (6)
N1R	0.645 (4)	0.020 (3)	0.583 (17)	0.044 (6)*	0.090 (6)
H1NR	0.6973	0.0034	0.5243	0.066*	0.090 (6)
H2NR	0.6660	0.0290	0.7089	0.066*	0.090 (6)
H3NR	0.6309	0.0446	0.5055	0.066*	0.090 (6)
C20R	0.547 (4)	−0.0089 (18)	0.601 (9)	0.032 (13)*	0.090 (6)
H20R	0.5625	−0.0331	0.7039	0.038*	0.090 (6)
C21R	0.524 (7)	−0.033 (3)	0.398 (12)	0.06 (2)*	0.090 (6)
H21A	0.5872	−0.0500	0.3553	0.097*	0.090 (6)
H21B	0.5067	−0.0104	0.2941	0.097*	0.090 (6)
H21C	0.4651	−0.0540	0.4151	0.097*	0.090 (6)
C22R	0.454 (4)	0.0187 (15)	0.684 (6)	0.051 (10)*	0.090 (6)
C23R	0.423 (5)	0.0604 (17)	0.599 (8)	0.082 (12)*	0.090 (6)
H23R	0.4612	0.0725	0.4870	0.098*	0.090 (6)
C24R	0.335 (5)	0.085 (2)	0.682 (9)	0.105 (12)*	0.090 (6)
H24R	0.3144	0.1128	0.6231	0.126*	0.090 (6)
C25R	0.282 (5)	0.068 (2)	0.843 (10)	0.100 (19)*	0.090 (6)
H25R	0.2252	0.0845	0.8988	0.120*	0.090 (6)
C26R	0.309 (6)	0.026 (3)	0.930 (12)	0.103 (19)*	0.090 (6)
H26R	0.2705	0.0144	1.0413	0.124*	0.090 (6)
C27R	0.394 (6)	0.002 (2)	0.850 (10)	0.076 (17)*	0.090 (6)
H27R	0.4129	−0.0262	0.9086	0.091*	0.090 (6)
N1P	0.6514 (5)	0.0126 (2)	0.5657 (16)	0.0488 (12)	0.910 (6)
H1NP	0.7057	−0.0061	0.5316	0.073*	0.910 (6)
H2NP	0.6612	0.0231	0.6941	0.073*	0.910 (6)
H3NP	0.6491	0.0363	0.4776	0.073*	0.910 (6)
C20P	0.5483 (6)	−0.0135 (2)	0.5550 (12)	0.0587 (19)	0.910 (6)
H20P	0.5535	−0.0396	0.6521	0.070*	0.910 (6)
C21P	0.5361 (8)	−0.0333 (3)	0.3408 (15)	0.084 (2)	0.910 (6)
H21D	0.5971	−0.0525	0.3096	0.126*	0.910 (6)
H21E	0.5321	−0.0085	0.2418	0.126*	0.910 (6)
H21F	0.4714	−0.0515	0.3340	0.126*	0.910 (6)
C22P	0.4567 (4)	0.01650 (19)	0.6251 (9)	0.0630 (14)	0.910 (6)
C23P	0.4226 (5)	0.0535 (2)	0.5059 (13)	0.097 (3)	0.910 (6)
H23P	0.4571	0.0597	0.3809	0.117*	0.910 (6)
C24P	0.3384 (6)	0.0813 (2)	0.5687 (15)	0.125 (3)	0.910 (6)
H24P	0.3160	0.1059	0.4864	0.150*	0.910 (6)
C25P	0.2879 (6)	0.0722 (3)	0.7545 (16)	0.128 (4)	0.910 (6)
H25P	0.2323	0.0913	0.7996	0.154*	0.910 (6)
C26P	0.3186 (8)	0.0355 (4)	0.8726 (14)	0.126 (3)	0.910 (6)
H26P	0.2828	0.0289	0.9961	0.151*	0.910 (6)
C27P	0.4039 (7)	0.0077 (3)	0.8077 (12)	0.093 (2)	0.910 (6)
H27P	0.4253	−0.0172	0.8895	0.112*	0.910 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1P	0.094 (3)	0.059 (2)	0.127 (4)	−0.003 (2)	−0.052 (3)	0.001 (2)
C1P	0.076 (4)	0.050 (3)	0.080 (4)	0.010 (3)	−0.017 (3)	0.009 (3)
C2P	0.092 (4)	0.048 (2)	0.054 (3)	0.019 (2)	0.003 (2)	0.012 (2)
C3P	0.070 (3)	0.061 (3)	0.101 (4)	0.006 (3)	0.018 (3)	0.023 (3)
C4P	0.067 (4)	0.053 (3)	0.125 (6)	−0.005 (3)	−0.037 (4)	0.011 (3)
C5P	0.107 (5)	0.052 (3)	0.057 (3)	0.005 (3)	−0.007 (3)	0.003 (2)
C6P	0.126 (5)	0.048 (3)	0.086 (4)	0.009 (3)	−0.009 (4)	−0.001 (3)
C7P	0.109 (5)	0.043 (3)	0.100 (4)	−0.002 (3)	−0.003 (4)	0.020 (3)
C8P	0.098 (5)	0.073 (4)	0.134 (6)	−0.010 (3)	0.014 (4)	0.039 (4)
C9P	0.101 (4)	0.055 (3)	0.080 (4)	0.026 (3)	−0.002 (3)	0.012 (3)
C10P	0.054 (4)	0.059 (4)	0.073 (3)	0.006 (2)	0.004 (2)	0.011 (2)
C11P	0.054 (3)	0.051 (2)	0.070 (3)	0.006 (2)	−0.013 (2)	0.006 (2)
C12P	0.048 (2)	0.042 (2)	0.056 (3)	0.0049 (18)	−0.006 (2)	0.0066 (19)
C13P	0.082 (4)	0.046 (3)	0.047 (3)	0.015 (2)	0.002 (2)	0.010 (2)
C14P	0.071 (4)	0.040 (3)	0.047 (3)	0.015 (2)	0.006 (2)	0.004 (2)
C15P	0.053 (3)	0.034 (2)	0.042 (2)	0.0073 (17)	0.002 (2)	0.0012 (18)
C16P	0.075 (3)	0.043 (2)	0.044 (2)	0.005 (2)	0.010 (3)	0.000 (2)
C17P	0.050 (3)	0.044 (2)	0.070 (3)	0.008 (2)	0.008 (3)	−0.003 (2)
C18P	0.059 (3)	0.031 (2)	0.043 (3)	0.0010 (18)	−0.002 (2)	0.0024 (18)
C19P	0.070 (4)	0.095 (4)	0.127 (6)	0.023 (3)	0.028 (4)	0.019 (4)
O2P	0.124 (4)	0.054 (2)	0.043 (2)	0.014 (3)	0.004 (2)	0.0134 (18)
O3P	0.078 (3)	0.056 (2)	0.053 (2)	0.028 (2)	−0.003 (2)	0.001 (2)
N1P	0.054 (2)	0.046 (3)	0.046 (3)	0.0145 (18)	−0.0007 (16)	0.003 (2)
C20P	0.068 (3)	0.046 (3)	0.062 (5)	0.005 (2)	−0.002 (3)	0.003 (3)
C21P	0.103 (6)	0.067 (4)	0.082 (6)	−0.004 (3)	−0.016 (5)	−0.017 (4)
C22P	0.058 (3)	0.056 (3)	0.075 (4)	−0.001 (2)	0.002 (3)	0.000 (3)
C23P	0.077 (4)	0.065 (3)	0.150 (7)	0.020 (3)	0.028 (4)	0.043 (4)
C24P	0.078 (4)	0.074 (4)	0.223 (10)	0.025 (3)	0.047 (6)	0.032 (6)
C25P	0.071 (4)	0.097 (6)	0.216 (12)	0.015 (4)	0.026 (7)	−0.026 (7)
C26P	0.097 (6)	0.163 (10)	0.118 (7)	0.034 (6)	0.019 (5)	−0.014 (6)
C27P	0.082 (4)	0.118 (6)	0.079 (5)	0.020 (4)	0.011 (4)	0.008 (4)

Geometric parameters (Å, º)

O1R—C11R	1.245 (16)	C5P—C10P	1.564 (7)
C1R—C2R	1.51 (2)	C6P—C7P	1.534 (8)
C1R—C9R	1.51 (2)	C7P—C9P	1.480 (7)
C1R—C10R	1.556 (19)	C7P—C8P	1.529 (8)
C2R—C3R	1.53 (2)	C10P—C19P	1.498 (7)
C3R—C4R	1.532 (11)	C10P—C11P	1.553 (7)
C3R—C8R	1.55 (2)	C11P—C12P	1.504 (5)
C4R—C5R	1.501 (11)	C12P—C13P	1.379 (5)
C5R—C10R	1.534 (19)	C12P—C17P	1.382 (5)
C5R—C6R	1.55 (2)	C13P—C14P	1.389 (6)
C6R—C7R	1.50 (2)	C14P—C15P	1.387 (6)
C7R—C8R	1.49 (2)	C15P—C16P	1.385 (5)
C7R—C9R	1.50 (2)	C15P—C18P	1.487 (5)
C10R—C11R	1.530 (15)	C16P—C17P	1.381 (5)
C10R—C19R	1.532 (19)	C18P—O2P	1.249 (5)
C11R—C12R	1.491 (12)	C18P—O3P	1.268 (4)
C12R—C13R	1.382 (16)	N1R—C20R	1.48 (2)
C12R—C17R	1.384 (15)	C20R—C22R	1.500 (11)
C13R—C14R	1.369 (14)	C20R—C21R	1.51 (2)
C14R—C15R	1.378 (15)	C22R—C23R	1.375 (9)
C15R—C16R	1.379 (15)	C22R—C27R	1.385 (9)
C15R—C18R	1.493 (12)	C23R—C24R	1.403 (9)
C16R—C17R	1.387 (14)	C24R—C25R	1.326 (9)
C18R—O2R	1.253 (10)	C25R—C26R	1.365 (9)
C18R—O3R	1.268 (10)	C26R—C27R	1.362 (9)
O1P—C11P	1.478 (6)	N1P—C20P	1.487 (6)
C1P—C9P	1.514 (7)	C20P—C22P	1.499 (7)
C1P—C2P	1.526 (7)	C20P—C21P	1.501 (9)
C1P—C10P	1.556 (9)	C22P—C27P	1.370 (6)
C2P—C3P	1.501 (7)	C22P—C23P	1.381 (6)
C2P—C11P	1.524 (7)	C23P—C24P	1.378 (6)
C3P—C4P	1.504 (7)	C24P—C25P	1.377 (7)
C3P—C8P	1.530 (7)	C25P—C26P	1.359 (7)
C4P—C5P	1.532 (7)	C26P—C27P	1.392 (7)
C5P—C6P	1.552 (6)
C2R—C1R—C9R	109 (2)	C9P—C7P—C8P	106.9 (5)
C2R—C1R—C10R	111 (2)	C9P—C7P—C6P	108.5 (5)
C9R—C1R—C10R	109 (2)	C8P—C7P—C6P	112.6 (5)
C1R—C2R—C3R	110 (2)	C7P—C8P—C3P	110.6 (5)
C2R—C3R—C4R	107 (2)	C7P—C9P—C1P	107.9 (4)
C2R—C3R—C8R	108 (2)	C19P—C10P—C11P	121.3 (5)
C4R—C3R—C8R	109 (2)	C19P—C10P—C1P	117.2 (5)
C5R—C4R—C3R	114 (2)	C11P—C10P—C1P	84.6 (5)
C4R—C5R—C10R	107 (2)	C19P—C10P—C5P	112.4 (7)
C4R—C5R—C6R	109 (2)	C11P—C10P—C5P	109.7 (4)
C10R—C5R—C6R	109 (2)	C1P—C10P—C5P	108.4 (4)
C7R—C6R—C5R	110 (2)	O1P—C11P—C12P	104.0 (3)
C8R—C7R—C9R	111 (3)	O1P—C11P—C2P	105.6 (4)
C8R—C7R—C6R	112 (3)	C12P—C11P—C2P	125.4 (4)
C9R—C7R—C6R	108 (2)	O1P—C11P—C10P	108.2 (4)
C7R—C8R—C3R	109 (2)	C12P—C11P—C10P	126.0 (5)
C7R—C9R—C1R	110 (2)	C2P—C11P—C10P	85.6 (4)
C11R—C10R—C19R	103.9 (13)	C13P—C12P—C17P	117.6 (3)
C11R—C10R—C5R	114 (2)	C13P—C12P—C11P	119.5 (4)
C19R—C10R—C5R	114 (2)	C17P—C12P—C11P	122.8 (4)
C11R—C10R—C1R	103.6 (19)	C12P—C13P—C14P	121.6 (4)
C19R—C10R—C1R	112 (3)	C15P—C14P—C13P	120.3 (4)
C5R—C10R—C1R	108.2 (19)	C16P—C15P—C14P	118.2 (4)
O1R—C11R—C12R	117.0 (13)	C16P—C15P—C18P	121.4 (4)
O1R—C11R—C10R	116.4 (11)	C14P—C15P—C18P	120.4 (4)
C12R—C11R—C10R	126.1 (12)	C17P—C16P—C15P	120.8 (4)
C13R—C12R—C17R	118.9 (9)	C16P—C17P—C12P	121.5 (4)
C13R—C12R—C11R	116.9 (12)	O2P—C18P—O3P	123.1 (4)
C17R—C12R—C11R	124.2 (12)	O2P—C18P—C15P	118.4 (4)
C14R—C13R—C12R	120.8 (11)	O3P—C18P—C15P	118.5 (4)
C13R—C14R—C15R	121.0 (11)	N1R—C20R—C22R	111.5 (15)
C14R—C15R—C16R	118.4 (9)	N1R—C20R—C21R	110 (3)
C14R—C15R—C18R	120.3 (12)	C22R—C20R—C21R	114 (3)
C16R—C15R—C18R	121.3 (12)	C23R—C22R—C27R	117.5 (7)
C15R—C16R—C17R	121.1 (11)	C23R—C22R—C20R	122.4 (9)
C12R—C17R—C16R	119.6 (11)	C27R—C22R—C20R	120.1 (9)
O2R—C18R—O3R	123.2 (14)	C22R—C23R—C24R	120.2 (8)
O2R—C18R—C15R	118.4 (12)	C25R—C24R—C23R	119.8 (8)
O3R—C18R—C15R	116.8 (12)	C24R—C25R—C26R	121.6 (8)
C9P—C1P—C2P	119.9 (5)	C27R—C26R—C25R	118.9 (8)
C9P—C1P—C10P	119.7 (5)	C26R—C27R—C22R	121.9 (8)
C2P—C1P—C10P	85.4 (4)	N1P—C20P—C22P	110.2 (4)
C3P—C2P—C11P	112.0 (4)	N1P—C20P—C21P	108.7 (5)
C3P—C2P—C1P	111.1 (4)	C22P—C20P—C21P	114.9 (6)
C11P—C2P—C1P	86.6 (4)	C27P—C22P—C23P	118.3 (4)
C2P—C3P—C4P	110.1 (4)	C27P—C22P—C20P	120.9 (5)
C2P—C3P—C8P	110.7 (5)	C23P—C22P—C20P	120.8 (5)
C4P—C3P—C8P	107.8 (6)	C24P—C23P—C22P	121.3 (5)
C3P—C4P—C5P	104.8 (5)	C25P—C24P—C23P	119.3 (5)
C4P—C5P—C6P	106.7 (5)	C26P—C25P—C24P	120.6 (5)
C4P—C5P—C10P	109.4 (4)	C25P—C26P—C27P	119.6 (6)
C6P—C5P—C10P	111.6 (4)	C22P—C27P—C26P	121.0 (5)
C7P—C6P—C5P	109.8 (4)

(94.5P)

Crystal data

C27H33NO3	Dx = 1.210 Mg m^−3
Mr = 419.54	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1822 reflections
a = 12.4288 (13) Å	θ = 6–20°
b = 28.809 (3) Å	µ = 0.08 mm^−1
c = 6.4326 (6) Å	T = 293 K
V = 2303.3 (4) Å^3	Block, colourless
Z = 4	0.56 × 0.41 × 0.20 mm
F(000) = 904

Data collection

Kuma KM4CCD diffractometer	3163 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.064
Graphite monochromator	θmax = 25.0°, θmin = 6.0°
ω scans	h = −14→13
10757 measured reflections	k = −34→34
3999 independent reflections	l = −6→7

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.078	w = 1/[σ^2(Fo^2) + (0.0788P)^2 + 1.5447P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.198	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.23 e Å^−3
3999 reflections	Δρmin = −0.20 e Å^−3
406 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
342 restraints	Extinction coefficient: 0.052 (9)
Primary atom site location: structure-invariant direct methods	Absolute structure: The absolute configuration was assigned to agree with that from Leibovitch M. et all, 1997; 1998
Secondary atom site location: inferred from neighbouring sites

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1R	0.404 (5)	0.2322 (16)	0.412 (5)	0.074 (16)*	0.055 (5)
C1R	0.387 (4)	0.3193 (16)	0.507 (7)	0.06 (2)*	0.055 (5)
H1R	0.3445	0.3098	0.3856	0.070*	0.055 (5)
C2R	0.506 (4)	0.318 (2)	0.452 (7)	0.088 (19)*	0.055 (5)
H2AR	0.5197	0.3384	0.3357	0.105*	0.055 (5)
H2BR	0.5261	0.2867	0.4123	0.105*	0.055 (5)
C3R	0.572 (4)	0.333 (2)	0.640 (9)	0.09 (2)*	0.055 (5)
H3R	0.6485	0.3328	0.6066	0.103*	0.055 (5)
C4R	0.547 (4)	0.3002 (19)	0.820 (8)	0.047 (16)*	0.055 (5)
H4AR	0.5679	0.2689	0.7802	0.056*	0.055 (5)
H4BR	0.5902	0.3090	0.9393	0.056*	0.055 (5)
C5R	0.431 (5)	0.3003 (17)	0.880 (6)	0.09 (2)*	0.055 (5)
H5R	0.4178	0.2793	0.9974	0.104*	0.055 (5)
C6R	0.395 (6)	0.3504 (19)	0.936 (8)	0.12 (2)*	0.055 (5)
H6AR	0.3189	0.3509	0.9655	0.140*	0.055 (5)
H6BR	0.4335	0.3608	1.0587	0.140*	0.055 (5)
C7R	0.419 (5)	0.3824 (16)	0.757 (10)	0.11 (2)*	0.055 (5)
H7R	0.3979	0.4139	0.7962	0.132*	0.055 (5)
C8R	0.536 (5)	0.3828 (17)	0.702 (11)	0.10 (3)*	0.055 (5)
H8AR	0.5781	0.3934	0.8199	0.120*	0.055 (5)
H8BR	0.5483	0.4040	0.5872	0.120*	0.055 (5)
C9R	0.354 (5)	0.3676 (17)	0.572 (10)	0.11 (2)*	0.055 (5)
H9AR	0.3660	0.3890	0.4582	0.134*	0.055 (5)
H9BR	0.2784	0.3680	0.6071	0.134*	0.055 (5)
C10R	0.368 (3)	0.2844 (13)	0.687 (7)	0.06 (3)*	0.055 (5)
C11R	0.414 (4)	0.2388 (14)	0.602 (6)	0.052 (11)*	0.055 (5)
C12R	0.468 (3)	0.2015 (12)	0.725 (5)	0.048 (11)*	0.055 (5)
C13R	0.549 (4)	0.1767 (16)	0.628 (5)	0.05 (3)*	0.055 (5)
H13R	0.5669	0.1837	0.4908	0.058*	0.055 (5)
C14R	0.603 (4)	0.1421 (17)	0.729 (5)	0.035 (11)*	0.055 (5)
H14R	0.6576	0.1263	0.6616	0.042*	0.055 (5)
C15R	0.577 (3)	0.1303 (14)	0.931 (5)	0.034 (11)*	0.055 (5)
C16R	0.497 (4)	0.1554 (18)	1.030 (5)	0.055 (19)*	0.055 (5)
H16R	0.4790	0.1483	1.1663	0.066*	0.055 (5)
C17R	0.443 (4)	0.1909 (18)	0.929 (6)	0.042 (16)*	0.055 (5)
H17R	0.3897	0.2076	0.9978	0.050*	0.055 (5)
C18R	0.636 (4)	0.0926 (17)	1.040 (6)	0.038 (6)*	0.055 (5)
C19R	0.251 (3)	0.274 (3)	0.731 (12)	0.13 (2)*	0.055 (5)
H19A	0.2158	0.3011	0.7831	0.197*	0.055 (5)
H19B	0.2457	0.2494	0.8316	0.197*	0.055 (5)
H19C	0.2160	0.2642	0.6042	0.197*	0.055 (5)
O2R	0.642 (8)	0.094 (3)	1.234 (6)	0.12 (3)*	0.055 (5)
O3R	0.695 (4)	0.0663 (17)	0.929 (7)	0.050 (18)*	0.055 (5)
O1P	0.3477 (3)	0.20680 (12)	0.5492 (7)	0.0934 (14)	0.945 (5)
HO1P	0.3751	0.1884	0.4677	0.140*	0.945 (5)
C1P	0.3822 (4)	0.29536 (16)	0.5318 (8)	0.0664 (13)	0.945 (5)
H1P	0.3217	0.2822	0.4542	0.080*	0.945 (5)
C2P	0.4820 (4)	0.26499 (13)	0.5021 (6)	0.0601 (12)	0.945 (5)
H2P	0.4901	0.2520	0.3621	0.072*	0.945 (5)
C3P	0.5803 (4)	0.28931 (17)	0.5842 (8)	0.0752 (15)	0.945 (5)
H3P	0.6448	0.2741	0.5293	0.090*	0.945 (5)
C4P	0.5819 (4)	0.28695 (19)	0.8176 (9)	0.0760 (17)	0.945 (5)
H4AP	0.6368	0.3073	0.8740	0.091*	0.945 (5)
H4BP	0.5956	0.2555	0.8646	0.091*	0.945 (5)
C5P	0.4694 (5)	0.30304 (15)	0.8837 (7)	0.0688 (15)	0.945 (5)
H5P	0.4594	0.2974	1.0327	0.083*	0.945 (5)
C6P	0.4654 (6)	0.35611 (15)	0.8396 (9)	0.0858 (18)	0.945 (5)
H6AP	0.3963	0.3684	0.8823	0.103*	0.945 (5)
H6BP	0.5210	0.3717	0.9191	0.103*	0.945 (5)
C7P	0.4825 (5)	0.36518 (17)	0.6077 (9)	0.0827 (17)	0.945 (5)
H7P	0.4890	0.3986	0.5832	0.099*	0.945 (5)
C8P	0.5817 (5)	0.34027 (19)	0.5228 (12)	0.097 (2)	0.945 (5)
H8AP	0.5832	0.3429	0.3725	0.117*	0.945 (5)
H8BP	0.6462	0.3549	0.5772	0.117*	0.945 (5)
C9P	0.3879 (5)	0.34692 (16)	0.4946 (9)	0.0808 (17)	0.945 (5)
H9AP	0.3949	0.3532	0.3471	0.097*	0.945 (5)
H9BP	0.3228	0.3618	0.5445	0.097*	0.945 (5)
C10P	0.3823 (4)	0.27606 (16)	0.7579 (9)	0.0582 (11)	0.945 (5)
C11P	0.4325 (3)	0.23192 (14)	0.6604 (7)	0.0557 (11)	0.945 (5)
C12P	0.4931 (3)	0.19452 (12)	0.7758 (6)	0.0482 (10)	0.945 (5)
C13P	0.5720 (4)	0.16961 (15)	0.6749 (7)	0.0554 (12)	0.945 (5)
H13P	0.5920	0.1781	0.5409	0.067*	0.945 (5)
C14P	0.6222 (4)	0.13218 (14)	0.7689 (6)	0.0513 (10)	0.945 (5)
H14P	0.6733	0.1152	0.6957	0.062*	0.945 (5)
C15P	0.5970 (3)	0.11992 (12)	0.9707 (6)	0.0404 (9)	0.945 (5)
C16P	0.5204 (4)	0.14562 (15)	1.0753 (7)	0.0548 (11)	0.945 (5)
H16P	0.5038	0.1384	1.2125	0.066*	0.945 (5)
C17P	0.4683 (4)	0.18202 (15)	0.9777 (7)	0.0551 (11)	0.945 (5)
H17P	0.4156	0.1984	1.0493	0.066*	0.945 (5)
C18P	0.6534 (4)	0.08010 (12)	1.0729 (5)	0.0432 (9)	0.945 (5)
C19P	0.2768 (4)	0.2744 (2)	0.8677 (11)	0.095 (2)	0.945 (5)
H19D	0.2862	0.2604	1.0019	0.142*	0.945 (5)
H19E	0.2267	0.2564	0.7877	0.142*	0.945 (5)
H19F	0.2496	0.3053	0.8844	0.142*	0.945 (5)
O2P	0.6558 (4)	0.07934 (12)	1.2663 (4)	0.0684 (11)	0.945 (5)
O3P	0.6944 (3)	0.04917 (13)	0.9592 (5)	0.0593 (9)	0.945 (5)
N1R	0.636 (6)	0.016 (4)	0.524 (16)	0.06 (2)*	0.055 (5)
H1NR	0.6864	−0.0020	0.4646	0.091*	0.055 (5)
H2NR	0.6626	0.0280	0.6403	0.091*	0.055 (5)
H3NR	0.6170	0.0382	0.4373	0.091*	0.055 (5)
C20R	0.541 (7)	−0.013 (3)	0.575 (14)	0.05 (2)*	0.055 (5)
H20R	0.5640	−0.0361	0.6787	0.063*	0.055 (5)
C21R	0.508 (9)	−0.040 (4)	0.381 (18)	0.06 (2)*	0.055 (5)
H21A	0.5678	−0.0569	0.3281	0.093*	0.055 (5)
H21B	0.4829	−0.0183	0.2775	0.093*	0.055 (5)
H21C	0.4505	−0.0608	0.4156	0.093*	0.055 (5)
C22R	0.453 (6)	0.015 (3)	0.670 (11)	0.053 (11)*	0.055 (5)
C23R	0.424 (8)	0.058 (3)	0.595 (12)	0.07 (2)*	0.055 (5)
H23R	0.4605	0.0706	0.4826	0.087*	0.055 (5)
C24R	0.340 (9)	0.083 (3)	0.689 (14)	0.111 (13)*	0.055 (5)
H24R	0.3193	0.1116	0.6360	0.133*	0.055 (5)
C25R	0.289 (8)	0.065 (4)	0.852 (15)	0.09 (2)*	0.055 (5)
H25R	0.2358	0.0825	0.9171	0.108*	0.055 (5)
C26R	0.314 (10)	0.022 (4)	0.929 (19)	0.12 (2)*	0.055 (5)
H26R	0.2766	0.0100	1.0405	0.139*	0.055 (5)
C27R	0.396 (9)	−0.002 (3)	0.838 (18)	0.08 (2)*	0.055 (5)
H27R	0.4134	−0.0313	0.8909	0.100*	0.055 (5)
N1P	0.6519 (4)	0.01286 (17)	0.5683 (7)	0.0473 (11)	0.945 (5)
H1NP	0.7062	−0.0058	0.5343	0.071*	0.945 (5)
H2NP	0.6615	0.0235	0.6969	0.071*	0.945 (5)
H3NP	0.6494	0.0366	0.4800	0.071*	0.945 (5)
C20P	0.5487 (5)	−0.0135 (2)	0.5576 (11)	0.0582 (17)	0.945 (5)
H20P	0.5538	−0.0396	0.6549	0.070*	0.945 (5)
C21P	0.5369 (6)	−0.0333 (2)	0.3420 (11)	0.080 (2)	0.945 (5)
H21D	0.5979	−0.0525	0.3109	0.120*	0.945 (5)
H21E	0.5329	−0.0084	0.2431	0.120*	0.945 (5)
H21F	0.4723	−0.0515	0.3347	0.120*	0.945 (5)
C22P	0.4568 (4)	0.01645 (18)	0.6256 (8)	0.0622 (14)	0.945 (5)
C23P	0.4231 (5)	0.0534 (2)	0.5061 (12)	0.097 (2)	0.945 (5)
H23P	0.4581	0.0598	0.3815	0.117*	0.945 (5)
C24P	0.3388 (6)	0.0812 (2)	0.5674 (15)	0.125 (3)	0.945 (5)
H24P	0.3165	0.1059	0.4847	0.150*	0.945 (5)
C25P	0.2877 (6)	0.0719 (3)	0.7527 (15)	0.126 (3)	0.945 (5)
H25P	0.2318	0.0910	0.7966	0.151*	0.945 (5)
C26P	0.3179 (7)	0.0353 (3)	0.8720 (13)	0.125 (3)	0.945 (5)
H26P	0.2817	0.0288	0.9952	0.150*	0.945 (5)
C27P	0.4036 (6)	0.0076 (3)	0.8085 (11)	0.089 (2)	0.945 (5)
H27P	0.4251	−0.0172	0.8910	0.107*	0.945 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1P	0.093 (3)	0.061 (2)	0.126 (3)	−0.0014 (19)	−0.052 (3)	0.000 (2)
C1P	0.072 (3)	0.049 (3)	0.079 (3)	0.010 (2)	−0.015 (3)	0.011 (2)
C2P	0.084 (3)	0.046 (2)	0.050 (2)	0.015 (2)	0.002 (2)	0.0090 (18)
C3P	0.067 (3)	0.059 (3)	0.099 (4)	0.007 (2)	0.019 (3)	0.021 (3)
C4P	0.059 (3)	0.051 (3)	0.118 (5)	−0.005 (3)	−0.035 (3)	0.012 (3)
C5P	0.100 (5)	0.048 (2)	0.059 (3)	0.009 (3)	−0.004 (3)	0.004 (2)
C6P	0.125 (5)	0.047 (3)	0.086 (3)	0.007 (3)	−0.007 (4)	−0.002 (3)
C7P	0.108 (5)	0.042 (3)	0.098 (4)	0.003 (3)	−0.002 (4)	0.018 (3)
C8P	0.088 (4)	0.070 (3)	0.135 (6)	−0.011 (3)	0.007 (4)	0.042 (4)
C9P	0.110 (4)	0.051 (3)	0.081 (3)	0.025 (3)	−0.006 (3)	0.012 (3)
C10P	0.053 (3)	0.054 (2)	0.068 (3)	0.010 (2)	0.004 (2)	0.010 (3)
C11P	0.052 (2)	0.045 (2)	0.070 (3)	0.003 (2)	−0.015 (2)	0.008 (2)
C12P	0.047 (2)	0.045 (2)	0.053 (2)	0.0067 (17)	−0.0028 (19)	0.0109 (18)
C13P	0.072 (3)	0.045 (2)	0.049 (2)	0.016 (2)	0.002 (2)	0.017 (2)
C14P	0.063 (3)	0.042 (2)	0.049 (2)	0.0189 (19)	0.005 (2)	0.0068 (18)
C15P	0.048 (2)	0.0327 (18)	0.0406 (18)	0.0090 (17)	−0.0001 (17)	0.0022 (16)
C16P	0.071 (3)	0.042 (2)	0.051 (2)	0.009 (2)	0.015 (2)	0.0079 (19)
C17P	0.052 (2)	0.041 (2)	0.073 (3)	0.016 (2)	0.010 (2)	0.004 (2)
C18P	0.054 (2)	0.0300 (18)	0.046 (2)	0.0038 (17)	−0.0017 (18)	0.0056 (16)
C19P	0.065 (3)	0.095 (4)	0.125 (5)	0.023 (3)	0.029 (3)	0.023 (4)
O2P	0.113 (3)	0.0472 (18)	0.0454 (16)	0.0169 (19)	−0.0007 (17)	0.0096 (14)
O3P	0.078 (2)	0.0448 (19)	0.0548 (17)	0.0271 (18)	−0.0058 (15)	−0.0001 (16)
N1P	0.056 (2)	0.0423 (19)	0.044 (2)	0.0128 (17)	−0.0044 (17)	0.0031 (18)
C20P	0.062 (3)	0.046 (2)	0.067 (3)	0.007 (2)	−0.001 (2)	0.003 (2)
C21P	0.092 (5)	0.066 (4)	0.084 (4)	−0.005 (3)	−0.015 (4)	−0.012 (3)
C22P	0.056 (3)	0.049 (2)	0.081 (4)	−0.002 (2)	0.001 (3)	0.004 (2)
C23P	0.073 (4)	0.064 (3)	0.155 (7)	0.018 (3)	0.026 (5)	0.037 (4)
C24P	0.077 (4)	0.071 (4)	0.228 (9)	0.021 (3)	0.041 (6)	0.034 (5)
C25P	0.067 (4)	0.095 (5)	0.216 (11)	0.020 (4)	0.012 (6)	−0.027 (7)
C26P	0.083 (5)	0.170 (9)	0.123 (6)	0.033 (5)	0.018 (4)	−0.019 (6)
C27P	0.078 (4)	0.107 (5)	0.083 (4)	0.016 (4)	0.008 (3)	0.006 (4)

Geometric parameters (Å, º)

O1R—C11R	1.239 (16)	C5P—C10P	1.560 (6)
C1R—C9R	1.51 (2)	C6P—C7P	1.529 (7)
C1R—C2R	1.52 (2)	C7P—C9P	1.479 (8)
C1R—C10R	1.553 (19)	C7P—C8P	1.528 (8)
C2R—C3R	1.52 (2)	C10P—C19P	1.490 (6)
C3R—C4R	1.531 (11)	C10P—C11P	1.549 (6)
C3R—C8R	1.55 (2)	C11P—C12P	1.509 (5)
C4R—C5R	1.501 (11)	C12P—C13P	1.378 (5)
C5R—C10R	1.536 (19)	C12P—C17P	1.383 (5)
C5R—C6R	1.55 (2)	C13P—C14P	1.385 (5)
C6R—C7R	1.50 (2)	C14P—C15P	1.381 (5)
C7R—C8R	1.49 (2)	C15P—C16P	1.381 (5)
C7R—C9R	1.50 (2)	C15P—C18P	1.497 (5)
C10R—C19R	1.515 (18)	C16P—C17P	1.383 (5)
C10R—C11R	1.539 (17)	C18P—O2P	1.245 (4)
C11R—C12R	1.492 (12)	C18P—O3P	1.260 (4)
C12R—C13R	1.381 (15)	N1R—C20R	1.48 (2)
C12R—C17R	1.382 (15)	C20R—C22R	1.499 (11)
C13R—C14R	1.366 (14)	C20R—C21R	1.52 (2)
C14R—C15R	1.382 (15)	C22R—C23R	1.375 (9)
C15R—C16R	1.379 (15)	C22R—C27R	1.385 (9)
C15R—C18R	1.487 (12)	C23R—C24R	1.403 (9)
C16R—C17R	1.384 (14)	C24R—C25R	1.326 (9)
C18R—O2R	1.255 (10)	C25R—C26R	1.365 (9)
C18R—O3R	1.271 (10)	C26R—C27R	1.363 (9)
O1P—C11P	1.465 (5)	N1P—C20P	1.493 (6)
C1P—C9P	1.506 (6)	C20P—C22P	1.497 (5)
C1P—C2P	1.529 (6)	C20P—C21P	1.506 (7)
C1P—C10P	1.557 (7)	C22P—C27P	1.374 (6)
C2P—C3P	1.504 (7)	C22P—C23P	1.379 (6)
C2P—C11P	1.524 (6)	C23P—C24P	1.376 (6)
C3P—C4P	1.503 (6)	C24P—C25P	1.377 (7)
C3P—C8P	1.520 (6)	C25P—C26P	1.357 (7)
C4P—C5P	1.533 (6)	C26P—C27P	1.392 (6)
C5P—C6P	1.556 (6)
C9R—C1R—C2R	110 (2)	C9P—C7P—C8P	107.4 (5)
C9R—C1R—C10R	110 (2)	C9P—C7P—C6P	108.0 (5)
C2R—C1R—C10R	108 (2)	C8P—C7P—C6P	112.3 (5)
C1R—C2R—C3R	109 (2)	C3P—C8P—C7P	110.6 (4)
C2R—C3R—C4R	108 (2)	C7P—C9P—C1P	108.1 (4)
C2R—C3R—C8R	109 (2)	C19P—C10P—C11P	121.3 (4)
C4R—C3R—C8R	109 (2)	C19P—C10P—C1P	117.0 (5)
C5R—C4R—C3R	113 (2)	C11P—C10P—C1P	85.1 (3)
C4R—C5R—C10R	106 (2)	C19P—C10P—C5P	112.4 (5)
C4R—C5R—C6R	110 (2)	C11P—C10P—C5P	109.8 (4)
C10R—C5R—C6R	109 (2)	C1P—C10P—C5P	107.9 (4)
C7R—C6R—C5R	110 (2)	O1P—C11P—C12P	104.3 (3)
C8R—C7R—C6R	112 (3)	O1P—C11P—C2P	105.8 (4)
C8R—C7R—C9R	110 (3)	C12P—C11P—C2P	125.0 (3)
C6R—C7R—C9R	109 (3)	O1P—C11P—C10P	108.2 (4)
C7R—C8R—C3R	109 (2)	C12P—C11P—C10P	126.0 (4)
C7R—C9R—C1R	110 (2)	C2P—C11P—C10P	85.4 (3)
C19R—C10R—C5R	113.6 (15)	C13P—C12P—C17P	117.7 (3)
C19R—C10R—C11R	104.8 (16)	C13P—C12P—C11P	119.7 (3)
C5R—C10R—C11R	111 (2)	C17P—C12P—C11P	122.5 (3)
C19R—C10R—C1R	114 (2)	C12P—C13P—C14P	121.4 (4)
C5R—C10R—C1R	109.5 (19)	C15P—C14P—C13P	120.5 (3)
C11R—C10R—C1R	103 (2)	C16P—C15P—C14P	118.5 (3)
O1R—C11R—C12R	117.3 (13)	C16P—C15P—C18P	121.3 (3)
O1R—C11R—C10R	116.3 (13)	C14P—C15P—C18P	120.2 (3)
C12R—C11R—C10R	126.4 (17)	C15P—C16P—C17P	120.5 (3)
C13R—C12R—C17R	118.7 (9)	C12P—C17P—C16P	121.3 (3)
C13R—C12R—C11R	117.2 (12)	O2P—C18P—O3P	123.9 (4)
C17R—C12R—C11R	124.1 (12)	O2P—C18P—C15P	117.6 (3)
C14R—C13R—C12R	121.0 (11)	O3P—C18P—C15P	118.4 (3)
C13R—C14R—C15R	121.0 (11)	N1R—C20R—C22R	112 (3)
C16R—C15R—C14R	118.0 (8)	N1R—C20R—C21R	109 (3)
C16R—C15R—C18R	121.6 (12)	C22R—C20R—C21R	114 (3)
C14R—C15R—C18R	120.3 (12)	C23R—C22R—C27R	117.5 (7)
C15R—C16R—C17R	121.3 (11)	C23R—C22R—C20R	122.5 (9)
C12R—C17R—C16R	119.8 (11)	C27R—C22R—C20R	120.0 (9)
O2R—C18R—O3R	122.9 (13)	C22R—C23R—C24R	120.3 (8)
O2R—C18R—C15R	118.5 (12)	C25R—C24R—C23R	119.7 (8)
O3R—C18R—C15R	117.2 (11)	C24R—C25R—C26R	121.6 (8)
C9P—C1P—C2P	120.4 (4)	C27R—C26R—C25R	119.0 (8)
C9P—C1P—C10P	120.0 (4)	C26R—C27R—C22R	121.8 (8)
C2P—C1P—C10P	85.0 (3)	N1P—C20P—C22P	110.3 (4)
C3P—C2P—C11P	112.6 (4)	N1P—C20P—C21P	108.6 (5)
C3P—C2P—C1P	110.4 (4)	C22P—C20P—C21P	114.4 (5)
C11P—C2P—C1P	87.0 (3)	C27P—C22P—C23P	118.3 (4)
C4P—C3P—C2P	109.9 (4)	C27P—C22P—C20P	120.7 (4)
C4P—C3P—C8P	107.6 (5)	C23P—C22P—C20P	121.0 (4)
C2P—C3P—C8P	111.6 (4)	C24P—C23P—C22P	121.4 (5)
C3P—C4P—C5P	104.6 (4)	C23P—C24P—C25P	119.1 (5)
C4P—C5P—C6P	106.0 (5)	C26P—C25P—C24P	120.9 (5)
C4P—C5P—C10P	109.8 (4)	C25P—C26P—C27P	119.4 (5)
C6P—C5P—C10P	111.9 (4)	C22P—C27P—C26P	120.9 (5)
C7P—C6P—C5P	110.0 (4)

(95.8P)

Crystal data

C27H33NO3	Dx = 1.211 Mg m^−3
Mr = 419.54	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1885 reflections
a = 12.4407 (12) Å	θ = 6–20°
b = 28.779 (2) Å	µ = 0.08 mm^−1
c = 6.4272 (6) Å	T = 293 K
V = 2301.1 (3) Å^3	Block, colourless
Z = 4	0.56 × 0.41 × 0.20 mm
F(000) = 904

Data collection

Kuma KM4CCD diffractometer	3194 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.063
Graphite monochromator	θmax = 25.0°, θmin = 6.0°
ω scans	h = −14→13
10741 measured reflections	k = −34→34
3994 independent reflections	l = −6→7

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.077	w = 1/[σ^2(Fo^2) + (0.0848P)^2 + 1.3604P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.198	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.20 e Å^−3
3994 reflections	Δρmin = −0.19 e Å^−3
406 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
348 restraints	Extinction coefficient: 0.049 (9)
Primary atom site location: structure-invariant direct methods	Absolute structure: The absolute configuration was assigned to agree with that from Leibovitch M. et all, 1997; 1998
Secondary atom site location: inferred from neighbouring sites

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1R	0.393 (5)	0.2355 (16)	0.410 (6)	0.055 (16)*	0.042 (4)
C1R	0.397 (4)	0.3260 (16)	0.494 (7)	0.033 (19)*	0.042 (4)
H1R	0.3545	0.3160	0.3736	0.040*	0.042 (4)
C2R	0.515 (5)	0.324 (2)	0.439 (9)	0.08 (2)*	0.042 (4)
H2AR	0.5288	0.3441	0.3193	0.100*	0.042 (4)
H2BR	0.5357	0.2929	0.4037	0.100*	0.042 (4)
C3R	0.583 (4)	0.341 (3)	0.623 (11)	0.08 (2)*	0.042 (4)
H3R	0.6598	0.3409	0.5870	0.096*	0.042 (4)
C4R	0.561 (5)	0.308 (2)	0.804 (11)	0.09 (2)*	0.042 (4)
H4AR	0.5809	0.2768	0.7634	0.104*	0.042 (4)
H4BR	0.6041	0.3170	0.9223	0.104*	0.042 (4)
C5R	0.444 (5)	0.3085 (18)	0.865 (7)	0.07 (2)*	0.042 (4)
H5R	0.4327	0.2881	0.9850	0.078*	0.042 (4)
C6R	0.408 (7)	0.359 (2)	0.917 (9)	0.12 (2)*	0.042 (4)
H6AR	0.3321	0.3590	0.9490	0.139*	0.042 (4)
H6BR	0.4469	0.3697	1.0391	0.139*	0.042 (4)
C7R	0.430 (6)	0.3903 (17)	0.737 (11)	0.10 (2)*	0.042 (4)
H7R	0.4086	0.4218	0.7751	0.118*	0.042 (4)
C8R	0.547 (6)	0.391 (2)	0.681 (13)	0.11 (5)*	0.042 (4)
H8AR	0.5887	0.4021	0.7986	0.127*	0.042 (4)
H8BR	0.5588	0.4118	0.5649	0.127*	0.042 (4)
C9R	0.365 (6)	0.3752 (17)	0.552 (11)	0.10 (2)*	0.042 (4)
H9AR	0.3785	0.3959	0.4357	0.123*	0.042 (4)
H9BR	0.2893	0.3764	0.5855	0.123*	0.042 (4)
C10R	0.378 (4)	0.2916 (12)	0.678 (7)	0.04 (2)*	0.042 (4)
C11R	0.416 (5)	0.2446 (13)	0.593 (6)	0.047 (11)*	0.042 (4)
C12R	0.468 (3)	0.2069 (12)	0.717 (5)	0.045 (18)*	0.042 (4)
C13R	0.546 (4)	0.1807 (16)	0.617 (5)	0.047 (11)*	0.042 (4)
H13R	0.5631	0.1872	0.4793	0.056*	0.042 (4)
C14R	0.598 (4)	0.1455 (18)	0.719 (6)	0.044 (11)*	0.042 (4)
H14R	0.6507	0.1288	0.6496	0.053*	0.042 (4)
C15R	0.572 (3)	0.1342 (14)	0.921 (5)	0.037 (11)*	0.042 (4)
C16R	0.497 (4)	0.1610 (18)	1.023 (5)	0.047 (19)*	0.042 (4)
H16R	0.4810	0.1550	1.1618	0.057*	0.042 (4)
C17R	0.443 (4)	0.1967 (18)	0.921 (6)	0.045 (18)*	0.042 (4)
H17R	0.3913	0.2139	0.9905	0.054*	0.042 (4)
C18R	0.631 (4)	0.0964 (16)	1.031 (6)	0.037 (6)*	0.042 (4)
C19R	0.259 (4)	0.284 (3)	0.726 (14)	0.12 (2)*	0.042 (4)
H19A	0.2283	0.3120	0.7785	0.175*	0.042 (4)
H19B	0.2523	0.2598	0.8294	0.175*	0.042 (4)
H19C	0.2223	0.2745	0.6019	0.175*	0.042 (4)
O2R	0.653 (7)	0.104 (3)	1.219 (7)	0.10 (2)*	0.042 (4)
O3R	0.687 (4)	0.0693 (18)	0.917 (7)	0.037 (15)*	0.042 (4)
O1P	0.3469 (3)	0.20664 (12)	0.5505 (7)	0.0905 (13)	0.958 (4)
HO1P	0.3740	0.1882	0.4688	0.136*	0.958 (4)
C1P	0.3817 (4)	0.29537 (15)	0.5305 (8)	0.0654 (12)	0.958 (4)
H1P	0.3213	0.2821	0.4528	0.078*	0.958 (4)
C2P	0.4811 (4)	0.26497 (13)	0.5010 (6)	0.0616 (12)	0.958 (4)
H2P	0.4891	0.2519	0.3610	0.074*	0.958 (4)
C3P	0.5794 (4)	0.28931 (16)	0.5821 (8)	0.0746 (14)	0.958 (4)
H3P	0.6437	0.2739	0.5276	0.090*	0.958 (4)
C4P	0.5806 (4)	0.28696 (16)	0.8160 (8)	0.0747 (15)	0.958 (4)
H4AP	0.6357	0.3072	0.8725	0.090*	0.958 (4)
H4BP	0.5942	0.2555	0.8628	0.090*	0.958 (4)
C5P	0.4690 (4)	0.30303 (15)	0.8839 (8)	0.0709 (15)	0.958 (4)
H5P	0.4594	0.2974	1.0331	0.085*	0.958 (4)
C6P	0.4655 (6)	0.35611 (15)	0.8396 (8)	0.0864 (17)	0.958 (4)
H6AP	0.3966	0.3686	0.8826	0.104*	0.958 (4)
H6BP	0.5213	0.3716	0.9188	0.104*	0.958 (4)
C7P	0.4824 (5)	0.36506 (15)	0.6072 (8)	0.0813 (16)	0.958 (4)
H7P	0.4891	0.3986	0.5830	0.098*	0.958 (4)
C8P	0.5812 (5)	0.34016 (19)	0.5190 (12)	0.0946 (19)	0.958 (4)
H8AP	0.5814	0.3426	0.3685	0.114*	0.958 (4)
H8BP	0.6461	0.3548	0.5713	0.114*	0.958 (4)
C9P	0.3864 (5)	0.34709 (17)	0.4939 (9)	0.0809 (16)	0.958 (4)
H9AP	0.3926	0.3536	0.3464	0.097*	0.958 (4)
H9BP	0.3216	0.3618	0.5457	0.097*	0.958 (4)
C10P	0.3809 (3)	0.27626 (15)	0.7580 (7)	0.0572 (11)	0.958 (4)
C11P	0.4317 (3)	0.23195 (13)	0.6595 (7)	0.0540 (10)	0.958 (4)
C12P	0.4921 (3)	0.19454 (11)	0.7755 (5)	0.0475 (9)	0.958 (4)
C13P	0.5707 (3)	0.16974 (13)	0.6741 (6)	0.0540 (10)	0.958 (4)
H13P	0.5901	0.1782	0.5396	0.065*	0.958 (4)
C14P	0.6217 (3)	0.13243 (13)	0.7674 (5)	0.0504 (9)	0.958 (4)
H14P	0.6731	0.1156	0.6940	0.061*	0.958 (4)
C15P	0.5964 (3)	0.12001 (11)	0.9696 (5)	0.0389 (8)	0.958 (4)
C16P	0.5196 (3)	0.14545 (13)	1.0744 (6)	0.0535 (10)	0.958 (4)
H16P	0.5028	0.1381	1.2115	0.064*	0.958 (4)
C17P	0.4673 (3)	0.18192 (13)	0.9769 (6)	0.0535 (10)	0.958 (4)
H17P	0.4143	0.1982	1.0485	0.064*	0.958 (4)
C18P	0.6530 (3)	0.08024 (11)	1.0724 (5)	0.0428 (8)	0.958 (4)
C19P	0.2767 (4)	0.2744 (2)	0.8689 (10)	0.0938 (18)	0.958 (4)
H19D	0.2867	0.2604	1.0029	0.141*	0.958 (4)
H19E	0.2264	0.2563	0.7894	0.141*	0.958 (4)
H19F	0.2493	0.3054	0.8862	0.141*	0.958 (4)
O2P	0.6553 (3)	0.07947 (10)	1.2662 (4)	0.0681 (10)	0.958 (4)
O3P	0.6944 (3)	0.04920 (11)	0.9587 (4)	0.0593 (8)	0.958 (4)
N1R	0.634 (6)	0.008 (4)	0.507 (14)	0.05 (2)*	0.042 (4)
H1NR	0.6808	−0.0110	0.4474	0.074*	0.042 (4)
H2NR	0.6594	0.0175	0.6294	0.074*	0.042 (4)
H3NR	0.6234	0.0327	0.4252	0.074*	0.042 (4)
C20R	0.531 (6)	−0.016 (3)	0.538 (12)	0.06 (2)*	0.042 (4)
H20R	0.5461	−0.0427	0.6301	0.068*	0.042 (4)
C21R	0.492 (7)	−0.037 (3)	0.333 (14)	0.041 (18)*	0.042 (4)
H21A	0.5492	−0.0543	0.2706	0.062*	0.042 (4)
H21B	0.4721	−0.0118	0.2408	0.062*	0.042 (4)
H21C	0.4315	−0.0563	0.3572	0.062*	0.042 (4)
C22R	0.450 (6)	0.013 (3)	0.648 (10)	0.058 (12)*	0.042 (4)
C23R	0.428 (9)	0.058 (3)	0.591 (15)	0.07 (2)*	0.042 (4)
H23R	0.4656	0.0716	0.4806	0.084*	0.042 (4)
C24R	0.351 (10)	0.084 (3)	0.698 (18)	0.111 (13)*	0.042 (4)
H24R	0.3365	0.1148	0.6586	0.134*	0.042 (4)
C25R	0.298 (9)	0.065 (4)	0.857 (18)	0.10 (2)*	0.042 (4)
H25R	0.2469	0.0830	0.9265	0.119*	0.042 (4)
C26R	0.318 (12)	0.021 (4)	0.92 (2)	0.12 (2)*	0.042 (4)
H26R	0.2807	0.0083	1.0314	0.147*	0.042 (4)
C27R	0.393 (10)	−0.005 (4)	0.816 (18)	0.06 (2)*	0.042 (4)
H27R	0.4061	−0.0350	0.8582	0.071*	0.042 (4)
N1P	0.6512 (3)	0.01303 (14)	0.5688 (6)	0.0456 (8)	0.958 (4)
H1NP	0.7057	−0.0055	0.5349	0.068*	0.958 (4)
H2NP	0.6608	0.0237	0.6975	0.068*	0.958 (4)
H3NP	0.6485	0.0368	0.4804	0.068*	0.958 (4)
C20P	0.5492 (4)	−0.01342 (17)	0.5585 (8)	0.0563 (12)	0.958 (4)
H20P	0.5546	−0.0394	0.6566	0.068*	0.958 (4)
C21P	0.5378 (5)	−0.0336 (2)	0.3433 (10)	0.0803 (16)	0.958 (4)
H21D	0.5990	−0.0528	0.3130	0.120*	0.958 (4)
H21E	0.5337	−0.0089	0.2434	0.120*	0.958 (4)
H21F	0.4736	−0.0520	0.3364	0.120*	0.958 (4)
C22P	0.4567 (4)	0.01639 (16)	0.6258 (8)	0.0630 (13)	0.958 (4)
C23P	0.4233 (5)	0.05350 (19)	0.5067 (11)	0.097 (2)	0.958 (4)
H23P	0.4589	0.0602	0.3830	0.117*	0.958 (4)
C24P	0.3380 (5)	0.0810 (2)	0.5675 (14)	0.121 (3)	0.958 (4)
H24P	0.3150	0.1054	0.4838	0.146*	0.958 (4)
C25P	0.2874 (5)	0.0718 (2)	0.7531 (14)	0.123 (3)	0.958 (4)
H25P	0.2316	0.0909	0.7978	0.148*	0.958 (4)
C26P	0.3182 (6)	0.0350 (3)	0.8719 (12)	0.122 (3)	0.958 (4)
H26P	0.2820	0.0283	0.9949	0.146*	0.958 (4)
C27P	0.4040 (6)	0.0074 (2)	0.8092 (11)	0.088 (2)	0.958 (4)
H27P	0.4259	−0.0174	0.8921	0.105*	0.958 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1P	0.087 (2)	0.061 (2)	0.123 (3)	0.0007 (18)	−0.046 (2)	0.000 (2)
C1P	0.071 (3)	0.053 (3)	0.072 (3)	0.007 (2)	−0.014 (2)	0.003 (2)
C2P	0.084 (3)	0.047 (2)	0.054 (2)	0.015 (2)	0.003 (2)	0.0076 (18)
C3P	0.067 (3)	0.062 (3)	0.095 (4)	0.009 (2)	0.017 (3)	0.020 (3)
C4P	0.063 (3)	0.047 (2)	0.114 (4)	−0.010 (2)	−0.035 (3)	0.014 (3)
C5P	0.106 (4)	0.047 (2)	0.061 (3)	0.011 (3)	−0.009 (3)	0.005 (2)
C6P	0.128 (5)	0.048 (3)	0.082 (3)	0.009 (3)	−0.009 (4)	−0.003 (2)
C7P	0.112 (4)	0.036 (2)	0.096 (4)	0.003 (3)	0.004 (3)	0.015 (2)
C8P	0.096 (4)	0.067 (3)	0.121 (5)	−0.009 (3)	0.007 (4)	0.030 (3)
C9P	0.111 (4)	0.048 (3)	0.083 (3)	0.026 (3)	−0.008 (3)	0.010 (2)
C10P	0.049 (2)	0.054 (2)	0.068 (3)	0.0080 (18)	0.007 (2)	0.012 (2)
C11P	0.052 (2)	0.040 (2)	0.070 (3)	0.0047 (18)	−0.013 (2)	0.009 (2)
C12P	0.049 (2)	0.0409 (19)	0.052 (2)	0.0083 (17)	−0.0032 (18)	0.0071 (18)
C13P	0.072 (3)	0.042 (2)	0.048 (2)	0.015 (2)	−0.0008 (19)	0.0125 (17)
C14P	0.060 (2)	0.044 (2)	0.047 (2)	0.0183 (18)	0.0045 (18)	0.0039 (17)
C15P	0.0485 (19)	0.0285 (16)	0.0395 (17)	0.0088 (15)	−0.0008 (16)	0.0036 (14)
C16P	0.070 (3)	0.043 (2)	0.048 (2)	0.008 (2)	0.014 (2)	0.0085 (18)
C17P	0.050 (2)	0.0394 (19)	0.071 (3)	0.0155 (18)	0.011 (2)	0.003 (2)
C18P	0.052 (2)	0.0292 (16)	0.0466 (19)	0.0034 (16)	−0.0034 (17)	0.0061 (15)
C19P	0.065 (3)	0.095 (4)	0.122 (5)	0.019 (3)	0.028 (3)	0.021 (4)
O2P	0.113 (3)	0.0474 (16)	0.0443 (15)	0.0141 (18)	−0.0029 (16)	0.0109 (13)
O3P	0.079 (2)	0.0456 (17)	0.0531 (16)	0.0279 (16)	−0.0053 (14)	−0.0001 (14)
N1P	0.0496 (19)	0.0414 (18)	0.046 (2)	0.0121 (15)	−0.0056 (16)	0.0012 (16)
C20P	0.061 (3)	0.043 (2)	0.065 (3)	0.005 (2)	−0.003 (2)	0.0049 (19)
C21P	0.087 (4)	0.067 (3)	0.087 (4)	−0.007 (3)	−0.016 (3)	−0.014 (3)
C22P	0.052 (2)	0.047 (2)	0.090 (3)	−0.0021 (19)	0.002 (2)	0.003 (2)
C23P	0.073 (3)	0.060 (3)	0.160 (7)	0.015 (3)	0.024 (4)	0.042 (4)
C24P	0.070 (4)	0.072 (3)	0.222 (9)	0.024 (3)	0.036 (5)	0.032 (5)
C25P	0.066 (4)	0.091 (5)	0.213 (10)	0.017 (3)	0.018 (6)	−0.032 (6)
C26P	0.082 (4)	0.166 (9)	0.117 (5)	0.025 (5)	0.022 (4)	−0.020 (5)
C27P	0.075 (4)	0.105 (5)	0.084 (4)	0.015 (4)	0.010 (3)	0.004 (4)

Geometric parameters (Å, º)

O1R—C11R	1.241 (16)	C5P—C10P	1.565 (6)
C1R—C9R	1.51 (2)	C6P—C7P	1.530 (7)
C1R—C2R	1.52 (2)	C7P—C9P	1.491 (7)
C1R—C10R	1.560 (19)	C7P—C8P	1.532 (8)
C2R—C3R	1.53 (2)	C10P—C19P	1.480 (6)
C3R—C4R	1.530 (11)	C10P—C11P	1.558 (5)
C3R—C8R	1.54 (2)	C11P—C12P	1.510 (4)
C4R—C5R	1.499 (11)	C12P—C13P	1.375 (5)
C5R—C10R	1.539 (19)	C12P—C17P	1.379 (5)
C5R—C6R	1.55 (2)	C13P—C14P	1.384 (4)
C6R—C7R	1.50 (2)	C14P—C15P	1.384 (4)
C7R—C8R	1.49 (2)	C15P—C16P	1.380 (4)
C7R—C9R	1.50 (2)	C15P—C18P	1.497 (4)
C10R—C19R	1.526 (19)	C16P—C17P	1.385 (5)
C10R—C11R	1.532 (15)	C18P—O2P	1.246 (4)
C11R—C12R	1.494 (12)	C18P—O3P	1.263 (4)
C12R—C17R	1.377 (15)	N1R—C20R	1.47 (2)
C12R—C13R	1.384 (15)	C20R—C22R	1.499 (11)
C13R—C14R	1.367 (14)	C20R—C21R	1.52 (2)
C14R—C15R	1.377 (15)	C22R—C23R	1.375 (9)
C15R—C16R	1.383 (15)	C22R—C27R	1.386 (9)
C15R—C18R	1.490 (13)	C23R—C24R	1.402 (9)
C16R—C17R	1.386 (14)	C24R—C25R	1.326 (9)
C18R—O2R	1.258 (10)	C25R—C26R	1.365 (9)
C18R—O3R	1.270 (10)	C26R—C27R	1.363 (9)
O1P—C11P	1.461 (5)	N1P—C20P	1.482 (6)
C1P—C9P	1.508 (6)	C20P—C22P	1.499 (5)
C1P—C2P	1.527 (6)	C20P—C21P	1.507 (6)
C1P—C10P	1.562 (6)	C22P—C27P	1.374 (6)
C2P—C3P	1.502 (7)	C22P—C23P	1.378 (5)
C2P—C11P	1.523 (5)	C23P—C24P	1.379 (6)
C3P—C4P	1.505 (6)	C24P—C25P	1.375 (7)
C3P—C8P	1.519 (6)	C25P—C26P	1.362 (7)
C4P—C5P	1.527 (6)	C26P—C27P	1.390 (6)
C5P—C6P	1.555 (5)
C9R—C1R—C2R	110 (2)	C9P—C7P—C6P	108.0 (5)
C9R—C1R—C10R	112 (2)	C9P—C7P—C8P	107.4 (5)
C2R—C1R—C10R	108 (2)	C6P—C7P—C8P	113.1 (5)
C1R—C2R—C3R	110 (2)	C3P—C8P—C7P	109.9 (4)
C2R—C3R—C4R	107 (2)	C7P—C9P—C1P	107.3 (4)
C2R—C3R—C8R	109 (2)	C19P—C10P—C11P	121.5 (4)
C4R—C3R—C8R	110 (2)	C19P—C10P—C1P	118.0 (4)
C5R—C4R—C3R	112 (2)	C11P—C10P—C1P	84.6 (3)
C4R—C5R—C10R	108 (2)	C19P—C10P—C5P	112.5 (4)
C4R—C5R—C6R	110 (2)	C11P—C10P—C5P	109.2 (3)
C10R—C5R—C6R	108 (2)	C1P—C10P—C5P	107.8 (4)
C7R—C6R—C5R	110 (2)	O1P—C11P—C12P	103.9 (3)
C8R—C7R—C6R	112 (3)	O1P—C11P—C2P	106.4 (4)
C8R—C7R—C9R	110 (3)	C12P—C11P—C2P	125.1 (3)
C6R—C7R—C9R	110 (3)	O1P—C11P—C10P	108.0 (3)
C7R—C8R—C3R	109 (2)	C12P—C11P—C10P	125.8 (3)
C7R—C9R—C1R	109 (2)	C2P—C11P—C10P	85.7 (3)
C19R—C10R—C11R	104.1 (16)	C13P—C12P—C17P	117.9 (3)
C19R—C10R—C5R	114 (3)	C13P—C12P—C11P	119.3 (3)
C11R—C10R—C5R	113 (2)	C17P—C12P—C11P	122.7 (3)
C19R—C10R—C1R	113 (3)	C12P—C13P—C14P	121.6 (3)
C11R—C10R—C1R	104 (2)	C15P—C14P—C13P	120.2 (3)
C5R—C10R—C1R	108.0 (19)	C16P—C15P—C14P	118.6 (3)
O1R—C11R—C12R	117.0 (12)	C16P—C15P—C18P	121.1 (3)
O1R—C11R—C10R	116.7 (11)	C14P—C15P—C18P	120.3 (3)
C12R—C11R—C10R	125.9 (12)	C15P—C16P—C17P	120.5 (3)
C17R—C12R—C13R	118.8 (9)	C12P—C17P—C16P	121.3 (3)
C17R—C12R—C11R	124.5 (12)	O2P—C18P—O3P	123.8 (3)
C13R—C12R—C11R	116.7 (12)	O2P—C18P—C15P	117.7 (3)
C14R—C13R—C12R	120.7 (11)	O3P—C18P—C15P	118.5 (3)
C13R—C14R—C15R	121.3 (11)	N1R—C20R—C22R	112 (3)
C14R—C15R—C16R	118.1 (9)	N1R—C20R—C21R	110 (3)
C14R—C15R—C18R	120.5 (12)	C22R—C20R—C21R	114 (3)
C16R—C15R—C18R	121.3 (12)	C23R—C22R—C27R	117.4 (7)
C15R—C16R—C17R	121.0 (11)	C23R—C22R—C20R	122.6 (9)
C12R—C17R—C16R	120.1 (11)	C27R—C22R—C20R	120.0 (9)
O2R—C18R—O3R	122.7 (15)	C22R—C23R—C24R	120.3 (8)
O2R—C18R—C15R	116 (3)	C25R—C24R—C23R	119.7 (8)
O3R—C18R—C15R	116 (2)	C24R—C25R—C26R	121.7 (8)
C9P—C1P—C2P	121.0 (4)	C27R—C26R—C25R	119.0 (8)
C9P—C1P—C10P	119.6 (4)	C26R—C27R—C22R	121.8 (8)
C2P—C1P—C10P	85.4 (3)	N1P—C20P—C22P	110.5 (3)
C3P—C2P—C11P	112.8 (3)	N1P—C20P—C21P	108.6 (4)
C3P—C2P—C1P	110.4 (4)	C22P—C20P—C21P	114.4 (4)
C11P—C2P—C1P	87.0 (3)	C27P—C22P—C23P	118.6 (4)
C2P—C3P—C4P	109.5 (4)	C27P—C22P—C20P	120.4 (4)
C2P—C3P—C8P	111.6 (4)	C23P—C22P—C20P	121.0 (4)
C4P—C3P—C8P	108.1 (5)	C22P—C23P—C24P	121.2 (5)
C3P—C4P—C5P	105.2 (4)	C25P—C24P—C23P	119.3 (5)
C4P—C5P—C6P	105.7 (4)	C26P—C25P—C24P	120.4 (5)
C4P—C5P—C10P	109.9 (3)	C25P—C26P—C27P	119.9 (5)
C6P—C5P—C10P	111.7 (4)	C22P—C27P—C26P	120.5 (5)
C7P—C6P—C5P	109.9 (4)

(96.2P)

Crystal data

C27H33NO3	Dx = 1.212 Mg m^−3
Mr = 419.54	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1937 reflections
a = 12.4509 (11) Å	θ = 6–20°
b = 28.753 (2) Å	µ = 0.08 mm^−1
c = 6.4239 (5) Å	T = 293 K
V = 2299.8 (3) Å^3	Block, colourless
Z = 4	0.56 × 0.41 × 0.20 mm
F(000) = 904

Data collection

Kuma KM4CCD diffractometer	3166 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.062
Graphite monochromator	θmax = 25.0°, θmin = 6.0°
ω scans	h = −14→13
10784 measured reflections	k = −34→34
3995 independent reflections	l = −6→7

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.075	w = 1/[σ^2(Fo^2) + (0.086P)^2 + 1.2282P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.196	(Δ/σ)max = 0.004
S = 1.07	Δρmax = 0.23 e Å^−3
3995 reflections	Δρmin = −0.18 e Å^−3
406 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
360 restraints	Extinction coefficient: 0.044 (9)
Primary atom site location: structure-invariant direct methods	Absolute structure: The absolute configuration was assigned to agree with that from Leibovitch M. et all, 1997; 1998
Secondary atom site location: inferred from neighbouring sites

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1R	0.394 (6)	0.235 (2)	0.411 (7)	0.073 (11)*	0.038 (4)
C1R	0.396 (5)	0.3243 (19)	0.503 (8)	0.06 (2)*	0.038 (4)
H1R	0.3534	0.3150	0.3814	0.068*	0.038 (4)
C2R	0.515 (6)	0.322 (3)	0.447 (10)	0.09 (2)*	0.038 (4)
H2AR	0.5289	0.3415	0.3277	0.102*	0.038 (4)
H2BR	0.5336	0.2902	0.4113	0.102*	0.038 (4)
C3R	0.582 (5)	0.338 (3)	0.632 (12)	0.07 (2)*	0.038 (4)
H3R	0.6588	0.3372	0.5971	0.087*	0.038 (4)
C4R	0.558 (6)	0.305 (3)	0.812 (12)	0.07 (2)*	0.038 (4)
H4AR	0.5770	0.2735	0.7713	0.087*	0.038 (4)
H4BR	0.6013	0.3133	0.9312	0.087*	0.038 (4)
C5R	0.442 (6)	0.306 (2)	0.873 (8)	0.08 (2)*	0.038 (4)
H5R	0.4290	0.2852	0.9922	0.091*	0.038 (4)
C6R	0.408 (7)	0.356 (2)	0.928 (10)	0.11 (2)*	0.038 (4)
H6AR	0.3321	0.3573	0.9601	0.128*	0.038 (4)
H6BR	0.4474	0.3667	1.0500	0.128*	0.038 (4)
C7R	0.432 (7)	0.3882 (18)	0.749 (12)	0.10 (2)*	0.038 (4)
H7R	0.4109	0.4199	0.7875	0.120*	0.038 (4)
C8R	0.548 (7)	0.388 (2)	0.691 (15)	0.11 (3)*	0.038 (4)
H8AR	0.5904	0.3990	0.8070	0.134*	0.038 (4)
H8BR	0.5595	0.4087	0.5738	0.134*	0.038 (4)
C9R	0.366 (6)	0.3734 (19)	0.563 (12)	0.10 (2)*	0.038 (4)
H9AR	0.3794	0.3943	0.4478	0.118*	0.038 (4)
H9BR	0.2902	0.3748	0.5975	0.118*	0.038 (4)
C10R	0.375 (4)	0.2896 (15)	0.684 (8)	0.05 (4)*	0.038 (4)
C11R	0.409 (5)	0.2422 (16)	0.599 (7)	0.050 (12)*	0.038 (4)
C12R	0.466 (4)	0.2049 (14)	0.719 (7)	0.044 (12)*	0.038 (4)
C13R	0.534 (5)	0.175 (2)	0.614 (6)	0.060 (12)*	0.038 (4)
H13R	0.5435	0.1782	0.4717	0.072*	0.038 (4)
C14R	0.587 (5)	0.140 (2)	0.717 (7)	0.044 (12)*	0.038 (4)
H14R	0.6331	0.1208	0.6436	0.053*	0.038 (4)
C15R	0.575 (4)	0.1338 (17)	0.929 (7)	0.039 (11)*	0.038 (4)
C16R	0.508 (5)	0.164 (2)	1.034 (6)	0.042 (12)*	0.038 (4)
H16R	0.4997	0.1613	1.1777	0.051*	0.038 (4)
C17R	0.453 (5)	0.199 (2)	0.931 (7)	0.049 (19)*	0.038 (4)
H17R	0.4066	0.2184	1.0045	0.059*	0.038 (4)
C18R	0.634 (5)	0.096 (2)	1.040 (7)	0.038 (6)*	0.038 (4)
C19R	0.256 (5)	0.284 (3)	0.733 (15)	0.10 (2)*	0.038 (4)
H19A	0.2281	0.3133	0.7842	0.155*	0.038 (4)
H19B	0.2463	0.2606	0.8365	0.155*	0.038 (4)
H19C	0.2180	0.2757	0.6085	0.155*	0.038 (4)
O2R	0.646 (8)	0.101 (3)	1.233 (7)	0.09 (2)*	0.038 (4)
O3R	0.692 (5)	0.069 (2)	0.931 (9)	0.04 (2)*	0.038 (4)
O1P	0.3462 (3)	0.20662 (11)	0.5508 (7)	0.0890 (12)	0.962 (4)
HO1P	0.3730	0.1881	0.4689	0.133*	0.962 (4)
C1P	0.3813 (4)	0.29542 (15)	0.5307 (8)	0.0644 (12)	0.962 (4)
H1P	0.3208	0.2821	0.4536	0.077*	0.962 (4)
C2P	0.4810 (4)	0.26495 (12)	0.5011 (6)	0.0592 (11)	0.962 (4)
H2P	0.4887	0.2518	0.3612	0.071*	0.962 (4)
C3P	0.5794 (4)	0.28926 (16)	0.5816 (8)	0.0720 (13)	0.962 (4)
H3P	0.6436	0.2738	0.5268	0.086*	0.962 (4)
C4P	0.5806 (4)	0.28701 (17)	0.8154 (8)	0.0727 (15)	0.962 (4)
H4AP	0.6357	0.3073	0.8716	0.087*	0.962 (4)
H4BP	0.5941	0.2555	0.8625	0.087*	0.962 (4)
C5P	0.4690 (4)	0.30327 (14)	0.8834 (7)	0.0680 (14)	0.962 (4)
H5P	0.4594	0.2977	1.0328	0.082*	0.962 (4)
C6P	0.4652 (5)	0.35636 (15)	0.8380 (8)	0.0823 (16)	0.962 (4)
H6AP	0.3962	0.3688	0.8807	0.099*	0.962 (4)
H6BP	0.5208	0.3720	0.9172	0.099*	0.962 (4)
C7P	0.4821 (5)	0.36524 (15)	0.6060 (8)	0.0793 (16)	0.962 (4)
H7P	0.4888	0.3988	0.5812	0.095*	0.962 (4)
C8P	0.5805 (5)	0.34020 (18)	0.5181 (11)	0.0936 (19)	0.962 (4)
H8AP	0.5806	0.3426	0.3675	0.112*	0.962 (4)
H8BP	0.6454	0.3549	0.5699	0.112*	0.962 (4)
C9P	0.3866 (5)	0.34701 (16)	0.4926 (8)	0.0779 (15)	0.962 (4)
H9AP	0.3932	0.3533	0.3448	0.093*	0.962 (4)
H9BP	0.3217	0.3619	0.5432	0.093*	0.962 (4)
C10P	0.3814 (3)	0.27643 (15)	0.7576 (8)	0.0560 (10)	0.962 (4)
C11P	0.4317 (3)	0.23196 (12)	0.6599 (6)	0.0532 (10)	0.962 (4)
C12P	0.4922 (3)	0.19459 (11)	0.7755 (5)	0.0462 (9)	0.962 (4)
C13P	0.5710 (3)	0.17002 (12)	0.6743 (6)	0.0534 (10)	0.962 (4)
H13P	0.5908	0.1787	0.5402	0.064*	0.962 (4)
C14P	0.6216 (3)	0.13260 (13)	0.7680 (6)	0.0504 (10)	0.962 (4)
H14P	0.6730	0.1158	0.6946	0.060*	0.962 (4)
C15P	0.5964 (3)	0.11999 (11)	0.9701 (5)	0.0393 (8)	0.962 (4)
C16P	0.5195 (3)	0.14553 (13)	1.0744 (6)	0.0534 (10)	0.962 (4)
H16P	0.5026	0.1382	1.2116	0.064*	0.962 (4)
C17P	0.4672 (3)	0.18201 (14)	0.9764 (6)	0.0538 (10)	0.962 (4)
H17P	0.4143	0.1983	1.0478	0.065*	0.962 (4)
C18P	0.6528 (3)	0.08028 (12)	1.0731 (5)	0.0423 (8)	0.962 (4)
C19P	0.2770 (4)	0.2746 (2)	0.8692 (10)	0.0910 (18)	0.962 (4)
H19D	0.2871	0.2606	1.0033	0.137*	0.962 (4)
H19E	0.2267	0.2566	0.7900	0.137*	0.962 (4)
H19F	0.2497	0.3056	0.8866	0.137*	0.962 (4)
O2P	0.6558 (3)	0.07955 (11)	1.2668 (4)	0.0690 (10)	0.962 (4)
O3P	0.6940 (3)	0.04919 (12)	0.9581 (4)	0.0585 (8)	0.962 (4)
N1R	0.650 (7)	0.017 (4)	0.500 (14)	0.038 (12)*	0.038 (4)
H1NR	0.6993	−0.0010	0.4397	0.058*	0.038 (4)
H2NR	0.6774	0.0299	0.6138	0.058*	0.038 (4)
H3NR	0.6298	0.0391	0.4115	0.058*	0.038 (4)
C20R	0.556 (9)	−0.012 (3)	0.56 (3)	0.05 (2)*	0.038 (4)
H20R	0.5808	−0.0350	0.6574	0.065*	0.038 (4)
C21R	0.518 (12)	−0.038 (9)	0.36 (4)	0.08 (2)*	0.038 (4)
H21A	0.5778	−0.0552	0.3069	0.127*	0.038 (4)
H21B	0.4919	−0.0166	0.2628	0.127*	0.038 (4)
H21C	0.4623	−0.0594	0.4023	0.127*	0.038 (4)
C22R	0.467 (7)	0.015 (3)	0.660 (17)	0.061 (12)*	0.038 (4)
C23R	0.434 (9)	0.058 (3)	0.594 (15)	0.06 (2)*	0.038 (4)
H23R	0.4685	0.0719	0.4815	0.066*	0.038 (4)
C24R	0.350 (9)	0.081 (4)	0.695 (19)	0.112 (13)*	0.038 (4)
H24R	0.3277	0.1102	0.6485	0.135*	0.038 (4)
C25R	0.303 (10)	0.061 (5)	0.86 (2)	0.11 (2)*	0.038 (4)
H25R	0.2476	0.0774	0.9255	0.128*	0.038 (4)
C26R	0.332 (12)	0.019 (5)	0.93 (2)	0.12 (2)*	0.038 (4)
H26R	0.2978	0.0053	1.0417	0.143*	0.038 (4)
C27R	0.413 (11)	−0.005 (4)	0.83 (2)	0.08 (2)*	0.038 (4)
H27R	0.4321	−0.0340	0.8744	0.099*	0.038 (4)
N1P	0.6509 (3)	0.01262 (13)	0.5686 (5)	0.0450 (9)	0.962 (4)
H1NP	0.7051	−0.0061	0.5346	0.067*	0.962 (4)
H2NP	0.6604	0.0232	0.6976	0.067*	0.962 (4)
H3NP	0.6487	0.0365	0.4806	0.067*	0.962 (4)
C20P	0.5481 (5)	−0.01367 (18)	0.5571 (12)	0.0566 (14)	0.962 (4)
H20P	0.5532	−0.0398	0.6547	0.068*	0.962 (4)
C21P	0.5370 (6)	−0.0336 (3)	0.3424 (16)	0.081 (2)	0.962 (4)
H21D	0.5981	−0.0528	0.3121	0.121*	0.962 (4)
H21E	0.5330	−0.0088	0.2427	0.121*	0.962 (4)
H21F	0.4728	−0.0520	0.3349	0.121*	0.962 (4)
C22P	0.4562 (4)	0.01615 (16)	0.6251 (8)	0.0614 (13)	0.962 (4)
C23P	0.4229 (5)	0.0531 (2)	0.5047 (11)	0.098 (2)	0.962 (4)
H23P	0.4581	0.0595	0.3802	0.117*	0.962 (4)
C24P	0.3385 (5)	0.0808 (2)	0.5655 (14)	0.123 (3)	0.962 (4)
H24P	0.3162	0.1054	0.4821	0.148*	0.962 (4)
C25P	0.2875 (5)	0.0717 (2)	0.7510 (14)	0.124 (3)	0.962 (4)
H25P	0.2317	0.0908	0.7950	0.148*	0.962 (4)
C26P	0.3178 (6)	0.0349 (3)	0.8708 (12)	0.123 (3)	0.962 (4)
H26P	0.2815	0.0284	0.9939	0.148*	0.962 (4)
C27P	0.4035 (5)	0.0073 (2)	0.8078 (10)	0.0863 (17)	0.962 (4)
H27P	0.4251	−0.0176	0.8907	0.104*	0.962 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1P	0.086 (2)	0.0598 (19)	0.121 (3)	−0.0033 (17)	−0.046 (2)	0.0013 (19)
C1P	0.069 (3)	0.052 (3)	0.072 (3)	0.009 (2)	−0.014 (2)	0.006 (2)
C2P	0.082 (3)	0.047 (2)	0.049 (2)	0.015 (2)	0.001 (2)	0.0105 (18)
C3P	0.061 (3)	0.061 (3)	0.094 (3)	0.010 (2)	0.019 (3)	0.021 (3)
C4P	0.059 (3)	0.048 (2)	0.111 (4)	−0.011 (2)	−0.029 (3)	0.015 (3)
C5P	0.103 (4)	0.046 (2)	0.055 (2)	0.012 (2)	−0.007 (3)	0.0029 (18)
C6P	0.121 (5)	0.045 (2)	0.081 (3)	0.011 (3)	−0.007 (3)	−0.001 (2)
C7P	0.105 (4)	0.038 (2)	0.095 (4)	0.002 (2)	−0.001 (3)	0.017 (2)
C8P	0.091 (4)	0.066 (3)	0.124 (5)	−0.010 (3)	0.005 (4)	0.037 (3)
C9P	0.108 (4)	0.049 (3)	0.077 (3)	0.021 (3)	−0.008 (3)	0.011 (2)
C10P	0.048 (2)	0.053 (2)	0.068 (3)	0.0080 (18)	0.005 (2)	0.011 (2)
C11P	0.050 (2)	0.0391 (19)	0.071 (2)	0.0030 (18)	−0.015 (2)	0.0081 (19)
C12P	0.045 (2)	0.0411 (18)	0.052 (2)	0.0065 (16)	−0.0020 (17)	0.0086 (17)
C13P	0.070 (3)	0.042 (2)	0.048 (2)	0.011 (2)	0.0048 (19)	0.0106 (17)
C14P	0.061 (2)	0.0411 (19)	0.049 (2)	0.0165 (18)	0.0033 (18)	0.0048 (17)
C15P	0.0467 (19)	0.0303 (16)	0.0408 (17)	0.0077 (15)	0.0008 (15)	0.0057 (14)
C16P	0.069 (3)	0.038 (2)	0.053 (2)	0.0066 (19)	0.018 (2)	0.0086 (17)
C17P	0.049 (2)	0.0399 (19)	0.072 (3)	0.0139 (18)	0.012 (2)	0.004 (2)
C18P	0.050 (2)	0.0288 (17)	0.0486 (19)	0.0030 (16)	−0.0008 (17)	0.0052 (15)
C19P	0.060 (3)	0.091 (4)	0.121 (5)	0.023 (3)	0.024 (3)	0.025 (3)
O2P	0.117 (3)	0.0471 (16)	0.0427 (15)	0.0142 (19)	−0.0022 (16)	0.0103 (12)
O3P	0.075 (2)	0.0460 (18)	0.0547 (16)	0.0261 (16)	−0.0065 (14)	−0.0016 (14)
N1P	0.0512 (18)	0.0413 (17)	0.0425 (19)	0.0128 (14)	−0.0034 (16)	0.0039 (17)
C20P	0.064 (3)	0.041 (2)	0.065 (3)	0.0052 (19)	−0.001 (2)	0.0047 (19)
C21P	0.097 (4)	0.063 (3)	0.083 (4)	−0.005 (3)	−0.015 (4)	−0.012 (3)
C22P	0.050 (2)	0.049 (2)	0.086 (3)	−0.0023 (19)	0.002 (2)	0.003 (2)
C23P	0.074 (4)	0.063 (3)	0.156 (7)	0.017 (3)	0.027 (4)	0.042 (4)
C24P	0.072 (4)	0.073 (4)	0.225 (9)	0.026 (3)	0.036 (5)	0.035 (5)
C25P	0.062 (3)	0.094 (5)	0.215 (9)	0.020 (3)	0.016 (5)	−0.031 (6)
C26P	0.083 (5)	0.163 (8)	0.122 (6)	0.029 (5)	0.021 (4)	−0.016 (5)
C27P	0.073 (3)	0.104 (5)	0.081 (4)	0.021 (3)	0.010 (3)	0.006 (3)

Geometric parameters (Å, º)

O1R—C11R	1.237 (17)	C5P—C10P	1.562 (6)
C1R—C9R	1.51 (2)	C6P—C7P	1.527 (7)
C1R—C2R	1.52 (2)	C7P—C9P	1.490 (7)
C1R—C10R	1.557 (19)	C7P—C8P	1.530 (8)
C2R—C3R	1.53 (2)	C10P—C19P	1.485 (6)
C3R—C4R	1.531 (11)	C10P—C11P	1.556 (5)
C3R—C8R	1.54 (2)	C11P—C12P	1.507 (4)
C4R—C5R	1.499 (11)	C12P—C13P	1.373 (4)
C5R—C10R	1.540 (19)	C12P—C17P	1.376 (5)
C5R—C6R	1.55 (2)	C13P—C14P	1.385 (4)
C6R—C7R	1.50 (2)	C14P—C15P	1.384 (4)
C7R—C8R	1.49 (2)	C15P—C16P	1.381 (4)
C7R—C9R	1.50 (2)	C15P—C18P	1.495 (4)
C10R—C19R	1.528 (19)	C16P—C17P	1.386 (5)
C10R—C11R	1.529 (16)	C18P—O2P	1.245 (4)
C11R—C12R	1.499 (16)	C18P—O3P	1.268 (4)
C12R—C17R	1.383 (16)	N1R—C20R	1.48 (2)
C12R—C13R	1.385 (16)	C20R—C22R	1.499 (11)
C13R—C14R	1.364 (15)	C20R—C21R	1.52 (2)
C14R—C15R	1.380 (16)	C22R—C23R	1.375 (9)
C15R—C16R	1.387 (16)	C22R—C27R	1.386 (9)
C15R—C18R	1.494 (17)	C23R—C24R	1.402 (9)
C16R—C17R	1.378 (15)	C24R—C25R	1.326 (9)
C18R—O2R	1.257 (11)	C25R—C26R	1.365 (9)
C18R—O3R	1.267 (11)	C26R—C27R	1.363 (9)
O1P—C11P	1.469 (5)	N1P—C20P	1.488 (6)
C1P—C9P	1.505 (6)	C20P—C22P	1.495 (5)
C1P—C2P	1.530 (6)	C20P—C21P	1.500 (6)
C1P—C10P	1.556 (6)	C22P—C27P	1.369 (5)
C2P—C3P	1.502 (7)	C22P—C23P	1.379 (6)
C2P—C11P	1.522 (5)	C23P—C24P	1.374 (6)
C3P—C4P	1.503 (6)	C24P—C25P	1.376 (7)
C3P—C8P	1.521 (6)	C25P—C26P	1.360 (7)
C4P—C5P	1.530 (6)	C26P—C27P	1.391 (6)
C5P—C6P	1.555 (5)
C9R—C1R—C2R	110 (3)	C9P—C7P—C6P	108.0 (5)
C9R—C1R—C10R	111 (2)	C9P—C7P—C8P	107.1 (4)
C2R—C1R—C10R	108 (2)	C6P—C7P—C8P	113.1 (5)
C1R—C2R—C3R	110 (2)	C3P—C8P—C7P	110.3 (4)
C2R—C3R—C4R	107 (2)	C7P—C9P—C1P	107.6 (4)
C2R—C3R—C8R	109 (2)	C19P—C10P—C11P	121.3 (4)
C4R—C3R—C8R	110 (2)	C19P—C10P—C1P	117.7 (4)
C5R—C4R—C3R	112 (2)	C11P—C10P—C1P	84.9 (3)
C4R—C5R—C10R	108 (2)	C19P—C10P—C5P	112.2 (4)
C4R—C5R—C6R	110 (2)	C11P—C10P—C5P	109.5 (3)
C10R—C5R—C6R	109 (2)	C1P—C10P—C5P	108.1 (4)
C7R—C6R—C5R	110 (2)	O1P—C11P—C12P	104.1 (3)
C8R—C7R—C6R	112 (3)	O1P—C11P—C2P	106.4 (3)
C8R—C7R—C9R	109 (3)	C12P—C11P—C2P	125.0 (3)
C6R—C7R—C9R	109 (3)	O1P—C11P—C10P	107.9 (3)
C7R—C8R—C3R	110 (2)	C12P—C11P—C10P	126.0 (3)
C7R—C9R—C1R	110 (2)	C2P—C11P—C10P	85.4 (3)
C19R—C10R—C11R	104.6 (16)	C13P—C12P—C17P	118.1 (3)
C19R—C10R—C5R	113 (3)	C13P—C12P—C11P	119.4 (3)
C11R—C10R—C5R	114 (2)	C17P—C12P—C11P	122.4 (3)
C19R—C10R—C1R	112 (3)	C12P—C13P—C14P	121.3 (3)
C11R—C10R—C1R	105 (2)	C15P—C14P—C13P	120.6 (3)
C5R—C10R—C1R	107.9 (19)	C16P—C15P—C14P	118.3 (3)
O1R—C11R—C12R	116.9 (13)	C16P—C15P—C18P	121.2 (3)
O1R—C11R—C10R	117.3 (13)	C14P—C15P—C18P	120.6 (3)
C12R—C11R—C10R	125.7 (13)	C15P—C16P—C17P	120.5 (3)
C17R—C12R—C13R	118.3 (10)	C12P—C17P—C16P	121.3 (3)
C17R—C12R—C11R	123 (2)	O2P—C18P—O3P	124.0 (3)
C13R—C12R—C11R	119 (2)	O2P—C18P—C15P	118.0 (3)
C14R—C13R—C12R	121.1 (11)	O3P—C18P—C15P	118.1 (3)
C13R—C14R—C15R	121.4 (11)	N1R—C20R—C22R	115 (3)
C14R—C15R—C16R	117.6 (10)	N1R—C20R—C21R	108 (3)
C14R—C15R—C18R	121 (2)	C22R—C20R—C21R	113 (3)
C16R—C15R—C18R	122 (2)	C23R—C22R—C27R	117.4 (7)
C17R—C16R—C15R	121.4 (11)	C23R—C22R—C20R	122.5 (9)
C16R—C17R—C12R	120.3 (11)	C27R—C22R—C20R	120.0 (9)
O2R—C18R—O3R	122.9 (15)	C22R—C23R—C24R	120.4 (8)
O2R—C18R—C15R	117 (3)	C25R—C24R—C23R	119.7 (8)
O3R—C18R—C15R	118 (3)	C24R—C25R—C26R	121.6 (8)
C9P—C1P—C2P	120.6 (4)	C27R—C26R—C25R	119.0 (8)
C9P—C1P—C10P	119.9 (4)	C26R—C27R—C22R	121.8 (8)
C2P—C1P—C10P	85.1 (3)	N1P—C20P—C22P	110.6 (3)
C3P—C2P—C11P	112.8 (3)	N1P—C20P—C21P	108.6 (4)
C3P—C2P—C1P	110.6 (3)	C22P—C20P—C21P	114.7 (4)
C11P—C2P—C1P	87.0 (3)	C27P—C22P—C23P	118.7 (4)
C2P—C3P—C4P	109.4 (4)	C27P—C22P—C20P	120.7 (4)
C2P—C3P—C8P	111.3 (4)	C23P—C22P—C20P	120.6 (4)
C4P—C3P—C8P	108.0 (5)	C24P—C23P—C22P	121.2 (5)
C3P—C4P—C5P	105.3 (4)	C23P—C24P—C25P	119.3 (5)
C4P—C5P—C6P	105.9 (4)	C26P—C25P—C24P	120.6 (5)
C4P—C5P—C10P	109.6 (3)	C25P—C26P—C27P	119.5 (5)
C6P—C5P—C10P	111.5 (4)	C22P—C27P—C26P	120.7 (5)
C7P—C6P—C5P	110.1 (4)

(100P)

Crystal data

C27H33NO3	Dx = 1.212 Mg m^−3
Mr = 419.54	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1944 reflections
a = 12.4537 (10) Å	θ = 6–20°
b = 28.749 (2) Å	µ = 0.08 mm^−1
c = 6.4240 (5) Å	T = 293 K
V = 2300.0 (3) Å^3	Block, colourless
Z = 4	0.56 × 0.41 × 0.20 mm
F(000) = 904

Data collection

Kuma KM4CCD diffractometer	3196 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.062
Graphite monochromator	θmax = 25.0°, θmin = 6.0°
ω scans	h = −14→13
10748 measured reflections	k = −34→34
3994 independent reflections	l = −6→7

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.079	w = 1/[σ^2(Fo^2) + (0.0813P)^2 + 1.4981P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.201	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.26 e Å^−3
3994 reflections	Δρmin = −0.22 e Å^−3
313 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.040 (8)
Primary atom site location: structure-invariant direct methods	Absolute structure: The absolute configuration was assigned to agree with that from Leibovitch M. et all, 1997; 1998
Secondary atom site location: difference Fourier map

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1P	0.3461 (3)	0.20650 (12)	0.5519 (7)	0.0923 (12)
HO1P	0.3726	0.1885	0.4675	0.138*
C1P	0.3821 (4)	0.29542 (16)	0.5303 (8)	0.0681 (12)
H1P	0.3216	0.2821	0.4531	0.082*
C2P	0.4810 (4)	0.26495 (14)	0.5006 (7)	0.0625 (11)
H2P	0.4890	0.2521	0.3602	0.075*
C3P	0.5789 (4)	0.28929 (16)	0.5820 (9)	0.0743 (13)
H3P	0.6433	0.2739	0.5275	0.089*
C4P	0.5800 (4)	0.28702 (16)	0.8148 (8)	0.0735 (14)
H4P1	0.6352	0.3072	0.8712	0.088*
H4P2	0.5932	0.2555	0.8618	0.088*
C5P	0.4679 (4)	0.30350 (15)	0.8829 (7)	0.0676 (13)
H5P	0.4583	0.2978	1.0322	0.081*
C6P	0.4649 (6)	0.35647 (16)	0.8388 (9)	0.0881 (17)
H6P1	0.3959	0.3690	0.8804	0.106*
H6P2	0.5203	0.3720	0.9190	0.106*
C7P	0.4829 (5)	0.36523 (15)	0.6069 (9)	0.0835 (16)
H7P	0.4897	0.3987	0.5817	0.100*
C8P	0.5805 (5)	0.34014 (18)	0.5192 (11)	0.0970 (19)
H8P1	0.5805	0.3426	0.3686	0.116*
H8P2	0.6455	0.3547	0.5710	0.116*
C9P	0.3870 (5)	0.34678 (16)	0.4932 (8)	0.0793 (15)
H9P1	0.3221	0.3616	0.5442	0.095*
H9P2	0.3934	0.3531	0.3454	0.095*
C10P	0.3814 (3)	0.27656 (15)	0.7576 (7)	0.0584 (10)
C11P	0.4308 (3)	0.23172 (13)	0.6578 (7)	0.0547 (10)
C12P	0.4926 (3)	0.19492 (12)	0.7757 (6)	0.0492 (9)
C13P	0.5706 (3)	0.17007 (13)	0.6723 (6)	0.0545 (10)
H13P	0.596 (3)	0.1818 (15)	0.521 (7)	0.064 (12)*
C14P	0.6210 (3)	0.13266 (13)	0.7672 (6)	0.0504 (9)
H14P	0.674 (3)	0.1138 (13)	0.683 (6)	0.044 (9)*
C15P	0.5964 (3)	0.12024 (11)	0.9705 (5)	0.0409 (8)
C16P	0.5186 (4)	0.14571 (13)	1.0741 (7)	0.0544 (10)
H16P	0.512 (4)	0.1388 (15)	1.224 (7)	0.066 (12)*
C17P	0.4674 (3)	0.18204 (14)	0.9759 (7)	0.0559 (10)
H17P	0.416 (4)	0.1979 (19)	1.052 (8)	0.084 (15)*
C18P	0.6525 (3)	0.08059 (11)	1.0720 (5)	0.0432 (8)
C19P	0.2765 (4)	0.2746 (2)	0.8678 (11)	0.0943 (18)
H19D	0.2247	0.2592	0.7814	0.141*
H19E	0.2525	0.3056	0.8973	0.141*
H19F	0.2847	0.2577	0.9958	0.141*
O2P	0.6555 (3)	0.07972 (10)	1.2667 (4)	0.0695 (9)
O3P	0.6940 (2)	0.04950 (10)	0.9583 (4)	0.0611 (8)
N1P	0.6511 (2)	0.01278 (10)	0.5668 (5)	0.0462 (7)
H1NP	0.6616	0.0231	0.6958	0.069*
H2NP	0.6478	0.0368	0.4797	0.069*
H3NP	0.7052	−0.0057	0.5304	0.069*
C20P	0.5488 (3)	−0.01362 (13)	0.5580 (7)	0.0539 (9)
H20P	0.5545	−0.0396	0.6559	0.065*
C21P	0.5364 (5)	−0.03379 (18)	0.3425 (8)	0.0828 (15)
H21D	0.5972	−0.0531	0.3112	0.124*
H21E	0.5321	−0.0090	0.2426	0.124*
H21F	0.4720	−0.0521	0.3364	0.124*
C22P	0.4569 (3)	0.01612 (15)	0.6266 (7)	0.0611 (11)
C23P	0.4236 (4)	0.05358 (18)	0.5061 (13)	0.099 (2)
H23P	0.470 (4)	0.0587 (18)	0.390 (8)	0.081 (15)*
C24P	0.3385 (5)	0.0809 (2)	0.5684 (19)	0.128 (3)
H24P	0.321 (6)	0.106 (3)	0.473 (12)	0.13 (2)*
C25P	0.2876 (6)	0.0714 (3)	0.7545 (19)	0.127 (3)
H25P	0.219 (7)	0.086 (3)	0.805 (11)	0.14 (2)*
C26P	0.3178 (5)	0.0345 (3)	0.8710 (13)	0.124 (3)
H26P	0.2812	0.0276	0.9934	0.149*
C27P	0.4038 (4)	0.0066 (2)	0.8086 (9)	0.0858 (16)
H27P	0.433 (6)	−0.020 (3)	0.915 (12)	0.15 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1P	0.088 (2)	0.0633 (19)	0.125 (3)	−0.0015 (17)	−0.053 (2)	0.000 (2)
C1P	0.070 (3)	0.056 (2)	0.078 (3)	0.009 (2)	−0.018 (2)	0.005 (2)
C2P	0.084 (3)	0.051 (2)	0.053 (2)	0.018 (2)	0.000 (2)	0.0097 (18)
C3P	0.071 (3)	0.057 (3)	0.094 (3)	0.008 (2)	0.016 (3)	0.019 (2)
C4P	0.064 (3)	0.052 (2)	0.104 (4)	−0.013 (2)	−0.031 (3)	0.011 (3)
C5P	0.097 (4)	0.050 (2)	0.056 (2)	0.017 (2)	−0.001 (2)	0.0025 (19)
C6P	0.131 (5)	0.050 (2)	0.084 (3)	0.007 (3)	−0.008 (3)	0.000 (2)
C7P	0.115 (4)	0.038 (2)	0.098 (4)	0.002 (3)	0.000 (3)	0.020 (2)
C8P	0.095 (4)	0.064 (3)	0.131 (5)	−0.009 (3)	0.008 (4)	0.038 (3)
C9P	0.106 (4)	0.054 (2)	0.079 (3)	0.024 (3)	−0.006 (3)	0.013 (2)
C10P	0.048 (2)	0.057 (2)	0.071 (2)	0.0092 (18)	0.004 (2)	0.011 (2)
C11P	0.050 (2)	0.0397 (19)	0.075 (3)	0.0002 (17)	−0.010 (2)	0.0036 (19)
C12P	0.052 (2)	0.0403 (18)	0.056 (2)	0.0051 (16)	0.0000 (18)	0.0071 (17)
C13P	0.071 (3)	0.0417 (19)	0.051 (2)	0.0095 (19)	0.0059 (19)	0.0076 (17)
C14P	0.060 (2)	0.0425 (18)	0.0486 (19)	0.0139 (18)	0.0070 (18)	0.0049 (17)
C15P	0.0468 (19)	0.0339 (16)	0.0421 (17)	0.0041 (14)	0.0034 (15)	0.0019 (14)
C16P	0.071 (3)	0.0408 (19)	0.052 (2)	0.0075 (18)	0.017 (2)	0.0071 (17)
C17P	0.051 (2)	0.0436 (19)	0.073 (3)	0.0119 (17)	0.013 (2)	0.0000 (19)
C18P	0.052 (2)	0.0321 (16)	0.0452 (18)	0.0026 (15)	−0.0028 (17)	0.0038 (15)
C19P	0.062 (3)	0.091 (4)	0.130 (5)	0.020 (3)	0.027 (3)	0.018 (4)
O2P	0.112 (3)	0.0511 (15)	0.0456 (15)	0.0152 (17)	−0.0028 (16)	0.0080 (12)
O3P	0.0756 (19)	0.0544 (16)	0.0532 (15)	0.0282 (14)	−0.0085 (14)	−0.0020 (13)
N1P	0.0516 (17)	0.0422 (15)	0.0447 (15)	0.0140 (13)	−0.0033 (14)	0.0020 (13)
C20P	0.056 (2)	0.0407 (19)	0.065 (2)	0.0057 (17)	−0.0015 (19)	0.0043 (18)
C21P	0.097 (4)	0.065 (3)	0.086 (3)	−0.004 (3)	−0.015 (3)	−0.014 (3)
C22P	0.048 (2)	0.051 (2)	0.085 (3)	−0.0020 (18)	−0.001 (2)	0.004 (2)
C23P	0.065 (3)	0.063 (3)	0.170 (6)	0.018 (2)	0.033 (4)	0.044 (4)
C24P	0.074 (4)	0.067 (4)	0.244 (10)	0.014 (3)	0.037 (6)	0.033 (5)
C25P	0.063 (4)	0.092 (5)	0.226 (10)	0.018 (3)	0.016 (5)	−0.032 (6)
C26P	0.083 (4)	0.169 (8)	0.121 (5)	0.020 (5)	0.023 (4)	−0.029 (5)
C27P	0.066 (3)	0.109 (4)	0.083 (3)	0.017 (3)	0.009 (3)	−0.002 (3)

Geometric parameters (Å, º)

O1P—C11P	1.450 (5)	C12P—C13P	1.376 (5)
C1P—C9P	1.497 (6)	C13P—C14P	1.387 (5)
C1P—C2P	1.523 (6)	C14P—C15P	1.388 (5)
C1P—C10P	1.558 (6)	C15P—C16P	1.385 (5)
C2P—C3P	1.500 (7)	C15P—C18P	1.488 (5)
C2P—C11P	1.524 (6)	C16P—C17P	1.377 (6)
C3P—C4P	1.497 (7)	C18P—O2P	1.252 (4)
C3P—C8P	1.517 (7)	C18P—O3P	1.265 (4)
C4P—C5P	1.537 (7)	N1P—C20P	1.484 (5)
C5P—C6P	1.549 (6)	C20P—C22P	1.495 (6)
C5P—C10P	1.552 (7)	C20P—C21P	1.509 (6)
C6P—C7P	1.528 (8)	C22P—C27P	1.370 (7)
C7P—C9P	1.498 (8)	C22P—C23P	1.389 (7)
C7P—C8P	1.521 (8)	C23P—C24P	1.377 (8)
C10P—C19P	1.486 (6)	C24P—C25P	1.381 (13)
C10P—C11P	1.566 (6)	C25P—C26P	1.352 (12)
C11P—C12P	1.512 (5)	C26P—C27P	1.397 (9)
C12P—C17P	1.375 (6)
C9P—C1P—C2P	121.0 (4)	O1P—C11P—C10P	108.5 (3)
C9P—C1P—C10P	119.5 (4)	C12P—C11P—C10P	124.8 (4)
C2P—C1P—C10P	85.5 (3)	C2P—C11P—C10P	85.2 (3)
C3P—C2P—C1P	110.2 (4)	C17P—C12P—C13P	118.2 (3)
C3P—C2P—C11P	113.3 (4)	C17P—C12P—C11P	122.8 (4)
C1P—C2P—C11P	86.9 (3)	C13P—C12P—C11P	118.7 (3)
C4P—C3P—C2P	109.6 (4)	C12P—C13P—C14P	120.7 (4)
C4P—C3P—C8P	107.9 (5)	C13P—C14P—C15P	120.9 (4)
C2P—C3P—C8P	111.6 (4)	C16P—C15P—C14P	118.1 (3)
C3P—C4P—C5P	105.2 (4)	C16P—C15P—C18P	121.5 (3)
C4P—C5P—C6P	105.9 (4)	C14P—C15P—C18P	120.4 (3)
C4P—C5P—C10P	109.2 (3)	C17P—C16P—C15P	120.3 (4)
C6P—C5P—C10P	112.2 (4)	C12P—C17P—C16P	121.8 (4)
C7P—C6P—C5P	109.7 (4)	O2P—C18P—O3P	123.4 (3)
C9P—C7P—C8P	106.8 (5)	O2P—C18P—C15P	117.9 (3)
C9P—C7P—C6P	107.4 (5)	O3P—C18P—C15P	118.7 (3)
C8P—C7P—C6P	113.6 (5)	N1P—C20P—C22P	110.7 (3)
C3P—C8P—C7P	110.4 (4)	N1P—C20P—C21P	108.6 (4)
C1P—C9P—C7P	107.7 (4)	C22P—C20P—C21P	114.3 (4)
C19P—C10P—C5P	112.5 (4)	C27P—C22P—C23P	119.1 (5)
C19P—C10P—C1P	117.7 (4)	C27P—C22P—C20P	120.4 (4)
C5P—C10P—C1P	107.9 (4)	C23P—C22P—C20P	120.5 (5)
C19P—C10P—C11P	120.6 (4)	C24P—C23P—C22P	120.6 (7)
C5P—C10P—C11P	110.5 (3)	C23P—C24P—C25P	119.5 (7)
C1P—C10P—C11P	84.3 (3)	C26P—C25P—C24P	120.4 (7)
O1P—C11P—C12P	104.8 (3)	C25P—C26P—C27P	120.3 (8)
O1P—C11P—C2P	107.5 (4)	C22P—C27P—C26P	120.0 (7)
C12P—C11P—C2P	124.2 (3)