(2R,4S)-3-N-(Fluoren-9-yl­methoxy­carbonyl)-4-methyl-2-nonyl­oxazolidin-5-one

Hughes, A.B.; Mackay, M.F.; Sleebs, M.

doi:10.1107/S1600536803013485

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(2R,4S)-3-N-(Fluoren-9-ylmethoxycarbonyl)-4-methyl-2-nonyloxazolidin-5-one

A. B. Hughes, M. F. Mackay and M. Sleebs

The title compound, C₃₈H₃₅NO₄, was isolated as one of two diastereoisomeric products. The molecule was found to have trans-configured n-nonyl and methyl substituents on the 5-oxazolidinone ring, the S configuration being assigned to C4 with reference to L-alanine. The n-nonyl group is fully extended and the oxazolidinone ring adopts a half-chair conformation.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803013485/dn6073sup1.cif Contains datablocks 2, oxazolidinone
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803013485/dn60732sup2.hkl Contains datablock 2

CCDC reference: 199844

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.005 Å
R factor = 0.053
wR factor = 0.151
Data-to-parameter ratio = 10.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_360  Alert C Short  C(sp3)-C(sp3) Bond  C13    -   C14      =       1.42 Ang.

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.50
         From the CIF: _reflns_number_total               3001
         Count of symmetry unique reflns         3040
         Completeness (_total/calc)             98.72%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Comment top

In the course of preparation of an N-alkyl-L-alanine derivative, the intermediate (1) was treated with n-decanal and camphorsulfonic acid in refluxing toluene. The reaction gave two diastereoisomeric 5-oxazolidinones, (2) and (3), as products in which the molecules have either trans- or cis-configured n-nonyl and methyl substituents about the 5-oxazolidinone ring. Other workers have prepared similar structures in studies concerned with the manipulation of α-amino acids generally for the construction of α,α-dialky-α-amino acids (see, for example, Karady et al., 1984). Compounds (2) and (3) were separated by column chromatography. As the ¹H NMR spectra of both compounds were similar we were unable to determine the configuration at the C2 asymmetric center, the S configuration being assigned to C4 with reference to L-alanine. Following column chromatography, the minor diastereoisomer crystallized and so an X-ray analysis was undertaken to ascertain its structure as either (2) or (3).

As structure (2) was found to have trans-configured n-nonyl and methyl substituents about the 5-oxazolidinone ring (Fig. 1), the configuration at C2 is R. The nonyl side chain at C2 is fully extended, the pertinent angles ranging from 176.9 (3) to 179.6 (4)°. The oxazolidinone ring adopts a half-chair conformation as indicated by the pseudo-rotation parameters (Altona et al., 1968) Δ = 1.5 and ϕ_m 21.1°. The fluorenyl substituent at C18 is not strictly planar as is generally observed for other fluorenyl moieties, but rather exhibits a slight bowing of the rings. The mean plane through the thirteen atoms shows that only five atoms C19, C21, C22, C29 and C30 lie −0.070 (3), 0.037 (3), 0.042 (3), 0.045 (4) and 0.032 (3) Å, respectively, from the plane whilst the other eight atoms lie roughly in the plane (r.m.s.d. < 0.02 Å). This characteristic, athough more pronounced, has been noted recently in another crystal structure containing a fluorenyl moiety (Meyers et al., 2001). The other dimensions associated with the central five-membered ring are similar to those generally observed for other comparable structures.

The crystal packing illustrated in Fig. 2 shows that the molecules are orientated in the crystal with the linear n-nonyl groups aligned along the b-crystal axis and adjacent to the fluorenyl moieties of adjacent molecules. Some intermolecular interaction between the two groups could account for the slight bowing of the fluorenyl rings. Intermolecular interactions also were suggested as causing this effect noticed previously.

Experimental top

N-Fmoc-L-alanine, (1) (500 mg, 1.6 mmol), camphorsulfonic acid (325 mg, 1.4 mmol) and acetic acid (92 ml, 1.6 mmol) were dissolved in toluene (200 ml). To this solution was added n-decanal (602 ml, 3.2 mmol) and the mixture was then heated under reflux (Dean–Stark trap) for 18 h. The solution was concentrated in vacuo and the residue was taken up in ethyl acetate. The solution was then washed with 5% sodium bicarbonate solution (3 × 50 ml). The organic phase was dried (MgSO₄) and concentrated in vacuo. The residue was purified by flash column chromatography, eluting with 10% ethyl acetate–hexane, to give the diastereoisomers (2) and (3) as a mixture (570 mg, 79%). A ¹³C NMR spectrum of the mixture indicated the ratio of compounds (2):(3) was approximately 1:2.6 (ratio obtained by integration of the methyl signals at δ 17.70 and 13.99 p.p.m., respectively). The diastereoisomers were separated by column chromatography, eluting with 25% diethyl ether–hexane. The first fraction eluted was the minor compound (2), and crystals (m.p. 350 K) were formed by slow evaporation from a solution of diethyl ether/n-hexane at room temperature.

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT; data reduction: SAINT; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. A perspective drawing of the molecule with displacement ellipsoids scaled to 40% probability and prepared from the output of ORTEPII (Johnson, 1976).
	Fig. 2. Stereoview of the crystal packing as viewed down the a-crystal axis with the c axis vertical. The larger open and lined cycles represent O and N atoms, respectively.

(2R,4S)-3-N-(Fluoren-9-ylmethoxycarbonyl)-4-methyl-2-nonyloxazolidin-5-one top

Crystal data top

C₂₈H₃₅NO₄	F(000) = 484
M_r = 449.59	D_x = 1.171 Mg m⁻³
Monoclinic, P2₁	Melting point: 350 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71065 Å
a = 5.140 (1) Å	Cell parameters from 5736 reflections
b = 15.575 (3) Å	θ = 5–27.5°
c = 16.050 (3) Å	µ = 0.08 mm⁻¹
β = 96.995 (3)°	T = 292 K
V = 1275.3 (4) Å³	Tabular, colourless
Z = 2	0.5 × 0.4 × 0.1 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	3001 independent reflections
Radiation source: fine-focus sealed tube	2268 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Blessing, 1995; Sheldrick, 1996)	h = −6→6
T_min = 0.964, T_max = 0.992	k = −20→20
11309 measured reflections	l = −20→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0928P)² + 0.0192P] where P = (F_o² + 2F_c²)/3
3001 reflections	(Δ/σ)_max = 0.001
300 parameters	Δρ_max = 0.17 e Å⁻³
1 restraint	Δρ_min = −0.10 e Å⁻³

Crystal data top

C₂₈H₃₅NO₄	V = 1275.3 (4) Å³
M_r = 449.59	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.140 (1) Å	µ = 0.08 mm⁻¹
b = 15.575 (3) Å	T = 292 K
c = 16.050 (3) Å	0.5 × 0.4 × 0.1 mm
β = 96.995 (3)°

Data collection top

Siemens SMART CCD area-detector diffractometer	3001 independent reflections
Absorption correction: multi-scan (SADABS; Blessing, 1995; Sheldrick, 1996)	2268 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.992	R_int = 0.018
11309 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	1 restraint
wR(F²) = 0.151	H-atom parameters constrained
S = 1.06	Δρ_max = 0.17 e Å⁻³
3001 reflections	Δρ_min = −0.10 e Å⁻³
300 parameters

Special details top

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 on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _ls _R_factor_gt etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	−0.4890 (4)	0.63848 (16)	0.14978 (14)	0.0831 (6)
C2	−0.2736 (5)	0.6970 (2)	0.16129 (19)	0.0701 (7)
H2	−0.3367	0.7548	0.1722	0.084*
N3	−0.1156 (5)	0.66390 (17)	0.23598 (15)	0.0724 (6)
C4	−0.1751 (6)	0.5742 (2)	0.2495 (2)	0.0802 (8)
H4	−0.0426	0.5373	0.2287	0.096*
C5	−0.4337 (7)	0.5664 (3)	0.1932 (2)	0.0840 (9)
O5	−0.5803 (6)	0.5066 (2)	0.1863 (2)	0.1187 (10)
C6	−0.2075 (8)	0.5507 (3)	0.3388 (3)	0.1027 (12)
H6A	−0.0413	0.5549	0.3730	0.154*
H6B	−0.2721	0.4930	0.3405	0.154*
H6C	−0.3299	0.5893	0.3597	0.154*
C7	−0.1360 (6)	0.6977 (2)	0.08408 (19)	0.0700 (7)
H7A	−0.0912	0.6392	0.0708	0.084*
H7B	0.0262	0.7297	0.0959	0.084*
C8	−0.2964 (6)	0.7367 (2)	0.0085 (2)	0.0761 (8)
H8A	−0.4611	0.7058	−0.0023	0.091*
H8B	−0.3365	0.7958	0.0211	0.091*
C9	−0.1625 (7)	0.7347 (3)	−0.0684 (2)	0.0884 (10)
H9A	−0.1280	0.6753	−0.0817	0.106*
H9B	0.0053	0.7634	−0.0565	0.106*
C10	−0.3130 (7)	0.7761 (3)	−0.1449 (2)	0.0874 (9)
H10A	−0.4846	0.7495	−0.1550	0.105*
H10B	−0.3391	0.8362	−0.1327	0.105*
C11	−0.1852 (8)	0.7699 (4)	−0.2226 (2)	0.1066 (13)
H11A	−0.0116	0.7948	−0.2112	0.128*
H11B	−0.1626	0.7095	−0.2346	0.128*
C12	−0.3181 (9)	0.8107 (3)	−0.2989 (2)	0.0971 (11)
H12A	−0.3306	0.8718	−0.2887	0.117*
H12B	−0.4953	0.7883	−0.3091	0.117*
C13	−0.1900 (8)	0.7981 (4)	−0.3759 (2)	0.1059 (12)
H13A	−0.0114	0.8189	−0.3641	0.127*
H13B	−0.1799	0.7368	−0.3855	0.127*
C14	−0.3006 (9)	0.8364 (5)	−0.4528 (3)	0.1256 (18)
H14A	−0.3081	0.8980	−0.4442	0.151*
H14B	−0.4796	0.8162	−0.4651	0.151*
C15	−0.1665 (10)	0.8209 (5)	−0.5273 (3)	0.1304 (19)
H15A	0.0189	0.8286	−0.5129	0.196*
H15B	−0.2298	0.8607	−0.5708	0.196*
H15C	−0.2009	0.7633	−0.5469	0.196*
C16	0.0843 (6)	0.7071 (2)	0.27956 (17)	0.0667 (7)
O16	0.2400 (5)	0.67758 (16)	0.33395 (14)	0.0842 (6)
O17	0.0848 (4)	0.78926 (14)	0.25331 (13)	0.0767 (6)
C18	0.2716 (6)	0.8441 (2)	0.30146 (19)	0.0710 (7)
H18A	0.4483	0.8274	0.2931	0.085*
H18B	0.2538	0.8390	0.3607	0.085*
C19	0.2209 (6)	0.9358 (2)	0.2730 (2)	0.0716 (7)
H19	0.0345	0.9495	0.2722	0.086*
C20	0.3848 (6)	0.99656 (19)	0.3316 (2)	0.0731 (7)
C21	0.3834 (7)	1.0102 (2)	0.4160 (2)	0.0840 (9)
H21	0.2649	0.9812	0.4452	0.101*
C22	0.5594 (8)	1.0675 (3)	0.4570 (3)	0.0953 (10)
H22	0.5595	1.0768	0.5143	0.114*
C23	0.7307 (9)	1.1098 (3)	0.4152 (3)	0.1011 (12)
H23	0.8485	1.1478	0.4442	0.121*
C24	0.7357 (8)	1.0982 (3)	0.3307 (3)	0.0982 (11)
H24	0.8552	1.1279	0.3024	0.118*
C25	0.5585 (6)	1.04125 (19)	0.2882 (2)	0.0745 (8)
C26	0.5114 (6)	1.0164 (2)	0.1989 (2)	0.0780 (8)
C27	0.6283 (9)	1.0427 (3)	0.1309 (3)	0.1006 (12)
H27	0.7650	1.0821	0.1378	0.121*
C28	0.5441 (10)	1.0111 (3)	0.0535 (3)	0.1097 (14)
H28	0.6245	1.0289	0.0076	0.132*
C29	0.3386 (11)	0.9523 (3)	0.0421 (2)	0.1074 (14)
H29	0.2807	0.9315	−0.0112	0.129*
C30	0.2220 (8)	0.9252 (2)	0.1100 (2)	0.0901 (10)
H30	0.0848	0.8859	0.1027	0.108*
C31	0.3084 (6)	0.9561 (2)	0.1888 (2)	0.0723 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0674 (11)	0.1033 (18)	0.0771 (12)	−0.0100 (12)	0.0032 (10)	−0.0045 (12)
C2	0.0631 (15)	0.0742 (17)	0.0710 (17)	0.0013 (13)	−0.0005 (13)	−0.0051 (14)
N3	0.0755 (14)	0.0694 (14)	0.0695 (14)	−0.0071 (12)	−0.0024 (11)	0.0066 (11)
C4	0.0782 (18)	0.0666 (17)	0.096 (2)	−0.0030 (15)	0.0087 (16)	0.0034 (16)
C5	0.077 (2)	0.088 (2)	0.087 (2)	−0.0146 (18)	0.0116 (16)	−0.0108 (18)
O5	0.1108 (19)	0.116 (2)	0.128 (2)	−0.0465 (19)	0.0076 (17)	−0.0058 (18)
C6	0.105 (3)	0.098 (3)	0.102 (3)	−0.013 (2)	−0.001 (2)	0.031 (2)
C7	0.0639 (14)	0.0751 (17)	0.0694 (16)	0.0048 (14)	0.0011 (12)	−0.0009 (14)
C8	0.0748 (17)	0.0811 (19)	0.0709 (18)	0.0102 (15)	0.0028 (14)	−0.0022 (15)
C9	0.0814 (19)	0.110 (3)	0.0728 (19)	0.0128 (19)	0.0050 (16)	0.0055 (18)
C10	0.097 (2)	0.089 (2)	0.077 (2)	0.0184 (18)	0.0095 (17)	0.0056 (17)
C11	0.096 (2)	0.145 (4)	0.080 (2)	0.019 (3)	0.0107 (19)	0.011 (2)
C12	0.107 (3)	0.107 (3)	0.077 (2)	0.017 (2)	0.0085 (19)	0.0080 (19)
C13	0.098 (2)	0.133 (4)	0.085 (2)	0.013 (3)	0.0011 (19)	0.006 (2)
C14	0.102 (3)	0.187 (5)	0.087 (3)	0.020 (3)	0.005 (2)	0.028 (3)
C15	0.110 (3)	0.195 (6)	0.086 (3)	0.020 (3)	0.011 (2)	0.025 (3)
C16	0.0716 (17)	0.0676 (17)	0.0598 (14)	−0.0037 (13)	0.0035 (13)	0.0009 (12)
O16	0.0853 (13)	0.0801 (14)	0.0816 (14)	−0.0003 (11)	−0.0132 (11)	0.0085 (11)
O17	0.0826 (12)	0.0717 (12)	0.0705 (12)	−0.0099 (10)	−0.0115 (9)	0.0047 (10)
C18	0.0751 (17)	0.0737 (18)	0.0617 (15)	−0.0082 (14)	−0.0020 (13)	−0.0003 (13)
C19	0.0646 (15)	0.0734 (18)	0.0756 (18)	0.0027 (14)	0.0037 (13)	−0.0034 (14)
C20	0.0674 (16)	0.0637 (16)	0.087 (2)	0.0063 (14)	0.0036 (14)	−0.0016 (14)
C21	0.092 (2)	0.081 (2)	0.079 (2)	−0.0017 (18)	0.0104 (16)	−0.0073 (17)
C22	0.113 (3)	0.082 (2)	0.088 (2)	−0.001 (2)	0.000 (2)	−0.0141 (18)
C23	0.107 (3)	0.082 (2)	0.109 (3)	−0.011 (2)	−0.007 (2)	−0.017 (2)
C24	0.098 (2)	0.077 (2)	0.119 (3)	−0.0120 (19)	0.010 (2)	0.010 (2)
C25	0.0771 (18)	0.0569 (15)	0.088 (2)	0.0033 (13)	0.0042 (15)	0.0031 (14)
C26	0.0803 (19)	0.0676 (17)	0.086 (2)	0.0152 (15)	0.0103 (15)	0.0182 (15)
C27	0.103 (3)	0.103 (3)	0.098 (3)	0.007 (2)	0.020 (2)	0.022 (2)
C28	0.139 (4)	0.103 (3)	0.092 (3)	0.024 (3)	0.033 (3)	0.032 (2)
C29	0.152 (4)	0.101 (3)	0.066 (2)	0.035 (3)	0.004 (2)	0.0103 (19)
C30	0.105 (2)	0.083 (2)	0.078 (2)	0.0088 (19)	−0.0055 (18)	0.0055 (17)
C31	0.0758 (17)	0.0654 (16)	0.0739 (18)	0.0133 (15)	0.0020 (14)	0.0058 (14)

Geometric parameters (Å, º) top

O1—C5	1.333 (5)	C14—H14A	0.9700
O1—C2	1.429 (4)	C14—H14B	0.9700
C2—N3	1.458 (4)	C15—H15A	0.9600
C2—C7	1.500 (4)	C15—H15B	0.9600
C2—H2	0.9800	C15—H15C	0.9600
N3—C16	1.350 (4)	C16—O16	1.202 (3)
N3—C4	1.453 (4)	C16—O17	1.347 (4)
C4—C6	1.507 (5)	O17—C18	1.439 (4)
C4—C5	1.518 (5)	C18—C19	1.512 (5)
C4—H4	0.9800	C18—H18A	0.9700
C5—O5	1.195 (5)	C18—H18B	0.9700
C6—H6A	0.9600	C19—C31	1.508 (5)
C6—H6B	0.9600	C19—C20	1.516 (4)
C6—H6C	0.9600	C19—H19	0.9800
C7—C8	1.508 (4)	C20—C21	1.372 (5)
C7—H7A	0.9700	C20—C25	1.385 (5)
C7—H7B	0.9700	C21—C22	1.379 (5)
C8—C9	1.486 (5)	C21—H21	0.9300
C8—H8A	0.9700	C22—C23	1.343 (6)
C8—H8B	0.9700	C22—H22	0.9300
C9—C10	1.513 (5)	C23—C24	1.372 (6)
C9—H9A	0.9700	C23—H23	0.9300
C9—H9B	0.9700	C24—C25	1.389 (5)
C10—C11	1.482 (5)	C24—H24	0.9300
C10—H10A	0.9700	C25—C26	1.477 (5)
C10—H10B	0.9700	C26—C27	1.371 (5)
C11—C12	1.473 (5)	C26—C31	1.398 (5)
C11—H11A	0.9700	C27—C28	1.356 (6)
C11—H11B	0.9700	C27—H27	0.9300
C12—C13	1.482 (6)	C28—C29	1.394 (7)
C12—H12A	0.9700	C28—H28	0.9300
C12—H12B	0.9700	C29—C30	1.372 (6)
C13—C14	1.425 (6)	C29—H29	0.9300
C13—H13A	0.9700	C30—C31	1.376 (5)
C13—H13B	0.9700	C30—H30	0.9300
C14—C15	1.471 (7)

C5—O1—C2	110.9 (3)	H13A—C13—H13B	106.9
O1—C2—N3	103.0 (2)	C13—C14—C15	117.3 (4)
O1—C2—C7	109.5 (2)	C13—C14—H14A	108.0
N3—C2—C7	114.2 (2)	C15—C14—H14A	108.0
O1—C2—H2	109.9	C13—C14—H14B	108.0
N3—C2—H2	109.9	C15—C14—H14B	108.0
C7—C2—H2	109.9	H14A—C14—H14B	107.2
C16—N3—C4	124.3 (3)	C14—C15—H15A	109.5
C16—N3—C2	124.2 (3)	C14—C15—H15B	109.5
C4—N3—C2	110.9 (2)	H15A—C15—H15B	109.5
N3—C4—C6	115.2 (3)	C14—C15—H15C	109.5
N3—C4—C5	99.9 (3)	H15A—C15—H15C	109.5
C6—C4—C5	110.9 (3)	H15B—C15—H15C	109.5
N3—C4—H4	110.2	O16—C16—O17	124.4 (3)
C6—C4—H4	110.2	O16—C16—N3	125.6 (3)
C5—C4—H4	110.2	O17—C16—N3	110.0 (2)
O5—C5—O1	121.0 (4)	C16—O17—C18	115.0 (2)
O5—C5—C4	127.8 (4)	O17—C18—C19	108.6 (2)
O1—C5—C4	111.1 (3)	O17—C18—H18A	110.0
C4—C6—H6A	109.5	C19—C18—H18A	110.0
C4—C6—H6B	109.5	O17—C18—H18B	110.0
H6A—C6—H6B	109.5	C19—C18—H18B	110.0
C4—C6—H6C	109.5	H18A—C18—H18B	108.3
H6A—C6—H6C	109.5	C31—C19—C18	114.2 (3)
H6B—C6—H6C	109.5	C31—C19—C20	102.8 (3)
C2—C7—C8	113.6 (2)	C18—C19—C20	109.8 (2)
C2—C7—H7A	108.8	C31—C19—H19	109.9
C8—C7—H7A	108.8	C18—C19—H19	109.9
C2—C7—H7B	108.8	C20—C19—H19	109.9
C8—C7—H7B	108.8	C21—C20—C25	120.0 (3)
H7A—C7—H7B	107.7	C21—C20—C19	129.8 (3)
C9—C8—C7	113.4 (3)	C25—C20—C19	110.2 (3)
C9—C8—H8A	108.9	C20—C21—C22	119.4 (4)
C7—C8—H8A	108.9	C20—C21—H21	120.3
C9—C8—H8B	108.9	C22—C21—H21	120.3
C7—C8—H8B	108.9	C23—C22—C21	120.7 (4)
H8A—C8—H8B	107.7	C23—C22—H22	119.7
C8—C9—C10	115.0 (3)	C21—C22—H22	119.7
C8—C9—H9A	108.5	C22—C23—C24	121.4 (4)
C10—C9—H9A	108.5	C22—C23—H23	119.3
C8—C9—H9B	108.5	C24—C23—H23	119.3
C10—C9—H9B	108.5	C23—C24—C25	118.7 (4)
H9A—C9—H9B	107.5	C23—C24—H24	120.7
C11—C10—C9	114.8 (3)	C25—C24—H24	120.7
C11—C10—H10A	108.6	C20—C25—C24	119.9 (3)
C9—C10—H10A	108.6	C20—C25—C26	108.5 (3)
C11—C10—H10B	108.6	C24—C25—C26	131.6 (3)
C9—C10—H10B	108.6	C27—C26—C31	120.1 (4)
H10A—C10—H10B	107.5	C27—C26—C25	131.2 (4)
C12—C11—C10	117.7 (3)	C31—C26—C25	108.7 (3)
C12—C11—H11A	107.9	C28—C27—C26	119.9 (4)
C10—C11—H11A	107.9	C28—C27—H27	120.1
C12—C11—H11B	107.9	C26—C27—H27	120.1
C10—C11—H11B	107.9	C27—C28—C29	120.7 (4)
H11A—C11—H11B	107.2	C27—C28—H28	119.6
C11—C12—C13	115.4 (4)	C29—C28—H28	119.6
C11—C12—H12A	108.4	C30—C29—C28	119.7 (4)
C13—C12—H12A	108.4	C30—C29—H29	120.2
C11—C12—H12B	108.4	C28—C29—H29	120.2
C13—C12—H12B	108.4	C29—C30—C31	119.9 (4)
H12A—C12—H12B	107.5	C29—C30—H30	120.0
C14—C13—C12	119.8 (4)	C31—C30—H30	120.0
C14—C13—H13A	107.4	C30—C31—C26	119.6 (3)
C12—C13—H13A	107.4	C30—C31—C19	130.7 (3)
C14—C13—H13B	107.4	C26—C31—C19	109.7 (3)
C12—C13—H13B	107.4

Experimental details

Crystal data
Chemical formula	C₂₈H₃₅NO₄
M_r	449.59
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	292
a, b, c (Å)	5.140 (1), 15.575 (3), 16.050 (3)
β (°)	96.995 (3)
V (Å³)	1275.3 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.5 × 0.4 × 0.1

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Blessing, 1995; Sheldrick, 1996)
T_min, T_max	0.964, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	11309, 3001, 2268
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.151, 1.06
No. of reflections	3001
No. of parameters	300
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.10

Computer programs: SMART (Siemens, 1995), SAINT, SHELXS86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.

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