17a-Allyl-17a-aza-d-homoandrost-4-en-3-one

Vasuki, G.; Parthasarathi, V.; Ramamurthi, K.; Piplani, P.; Jindal, D.P.

doi:10.1107/S160053680201992X

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17a-Allyl-17a-aza-D-homoandrost-4-en-3-one

G. Vasuki, V. Parthasarathi, K. Ramamurthi, P. Piplani and D. P. Jindal

The title compound, C₂₂H₃₃NO, a homoandrost-4-ene, is composed of four six-membered rings. Ring A adopts a 1α-sofa conformation, while the other rings adopt chair conformations. The crystal structure is stabilized by weak intermolecular C—H

O interactions and van der Waals forces.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680201992X/ci6175sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680201992X/ci6175Isup2.hkl Contains datablock I

CCDC reference: 202326

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.046
wR factor = 0.119
Data-to-parameter ratio = 8.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           24.97
         From the CIF: _reflns_number_total               1910
         Count of symmetry unique reflns         1942
         Completeness (_total/calc)             98.35%
         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.

Comment top

The X-ray investigation of the title compound, (I), was undertaken as part of a study on the structure and conformation of new synthetic steroid derivatives (Hema et al., 2002; Vasuki et al., 2001; Vasuki, Parthasarathi, Ramamurthi, Dubey & Jindal, 2002a,b,c; Vasuki, Parthasarathi, Ramamurthi, Jindal & Dubey, 2002; Vasuki, Thamotharan et al., 2002a,b). Compound (I), consisting of four six-membered fused rings, is a steroid with the normal 8β, 9α, 10β, 13β and 14α configuration. We are particularly interested to study the conformational flexibility of the steroid due to the substitution of the allyl moiety at position 17a.

In (I), ring A adopts a sofa conformation, with atom C1 in the α-position, as is evident from the deviation of C1 by 0.571 (4) Å from the mean C2/C3/C4/C5/C10 plane. Rings B and C adopt slightly distorted chair conformations, with Cremer & Pople (1975) puckering parameters Q = 0.538 (5) Å, θ = 10.4 (5)° and ϕ =188.1 (7)° for ring B, and Q = 0.561 (5) Å, θ = 9.1 (5)° and ϕ = 241.7 (8)° for ring C. Ring D adopts a normal chair conformation, with Q = 0.564 (5) Å, θ = 1.8 (5)° and ϕ = 98.4 (6)°. The allyl group at N17A shows a β-orientation. The C13—N17A—C20—C21 torsion angle is −163.9 (3)°; thus, the allyl moiety is antiperiplanar with respect to the C13—N17A bond. The B/C and C/D ring junctions are all trans. The widening of the exocyclic angle C13—N17A—C20 [113.3 (2)°] may be due to the steric interactions between atoms H12A and H20B (H12A···H20B = 1.99 Å). The C2—C3 (Csp³—Csp²) bond distance of 1.490 (6) Å is comparable with the reported value of 1.489 (5) Å in a related structure (Vasuki, Parthasarathi, Ramamurthi, Jindal & Dubey, 2002), which also shows a 1α-sofa conformation for the ring A. The C4—C5 (Csp²—Csp²) distance of 1.340 (5) Å confirms the localization of a double bond at this position. The mean Csp³—Csp³ bond length in (I) is calculated as 1.528 (2) Å. However, the C10—C9 (Csp³—Csp³) distance of 1.559 (4) Å has the largest deviation from the mean value. A similar larger value for this bond has been observed in some related structures, e.g. 1.567 (2) (Duax & Norton, 1975), 1.559 (3) (Paixao et al., 1998), 1.564 (3) (Vasuki, Parthasarathi, Ramamurthi, Dubey & Jindal, 2002a), and 1.560 (3) and 1.556 (3) Å in two independent molecules (Vasuki, Thamotharan et al., 2002b). The C3···C16 distance of 8.98 Å, which is a measure of the length of the steroid nucleus, indicates that the molecule is in a completely extended form (Isabella, 1970). The pseudo-torsion angle C19—C10··· C13—C18 in (I) is 0.4 (3)°. A short intermolecular C—H···O contact is observed between atoms C6 and O3ⁱ, with an H6B···O3ⁱ distance of 2.59 Å [symmetry code: (i) −x, 1/2 + y, 1/2 − z]. The structure is stabilized by van der Walls interactions.

Experimental top

The title compound was prepared by refluxing 17a-aza-D-homoandrost-4-en-3-one (1 g, 3.48 mmol), allyl bromide (1 ml) and dry methylketone (50 ml) for 15 min, and then adding anhydrous potassium carbonate (1 g). The reaction mixture was refluxed for 4 h with continuous stirring. The slurry obtained was filtered and the solvent was removed under reduced pressure. The residue obtained was crystallized from n-hexane to afford crystals of (I) (0.85 g, 74.63%; m.p.: 403–408 K).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP97 (Zsolnai, 1997); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.

17a-Allyl-17a-aza-D-homoandrost-4-en-3-one top

Crystal data top

C₂₂H₃₃NO	F(000) = 720
M_r = 327.49	D_x = 1.136 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 7.358 (2) Å	θ = 10–15°
b = 12.635 (2) Å	µ = 0.07 mm⁻¹
c = 20.596 (10) Å	T = 293 K
V = 1914.8 (12) Å³	Plate, green
Z = 4	0.20 × 0.17 × 0.17 mm

Data collection top

Enraf-Nonius CAD-4 diffractometer	R_int = 0.027
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 2.6°
Graphite monochromator	h = 0→8
ω–2θ scans	k = −4→15
1992 measured reflections	l = −7→24
1910 independent reflections	2 standard reflections every 120 min
1228 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0623P)² + 0.1373P] where P = (F_o² + 2F_c²)/3
1910 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.12 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₂H₃₃NO	V = 1914.8 (12) Å³
M_r = 327.49	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.358 (2) Å	µ = 0.07 mm⁻¹
b = 12.635 (2) Å	T = 293 K
c = 20.596 (10) Å	0.20 × 0.17 × 0.17 mm

Data collection top

Enraf-Nonius CAD-4 diffractometer	R_int = 0.027
1992 measured reflections	2 standard reflections every 120 min
1910 independent reflections	intensity decay: none
1228 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.03	Δρ_max = 0.12 e Å⁻³
1910 reflections	Δρ_min = −0.15 e Å⁻³
217 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 of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.5975 (6)	0.4834 (3)	0.1364 (2)	0.0809 (13)
H1A	0.4784	0.5162	0.1356	0.097*
H1B	0.6358	0.4730	0.0918	0.097*
C2	0.5821 (7)	0.3755 (3)	0.1694 (3)	0.0981 (15)
H2A	0.5252	0.3842	0.2116	0.118*
H2B	0.5051	0.3298	0.1435	0.118*
C3	0.7632 (7)	0.3245 (3)	0.17794 (19)	0.0846 (13)
O3	0.7790 (6)	0.2289 (2)	0.18108 (16)	0.1244 (14)
C4	0.9188 (6)	0.3950 (3)	0.18548 (16)	0.0707 (11)
H4	1.0329	0.3649	0.1914	0.085*
C5	0.9067 (5)	0.5009 (3)	0.18438 (14)	0.0573 (9)
C6	1.0675 (5)	0.5680 (3)	0.20174 (17)	0.0695 (11)
H6A	1.1756	0.5241	0.2015	0.083*
H6B	1.0515	0.5946	0.2456	0.083*
C7	1.0974 (5)	0.6615 (3)	0.15624 (18)	0.0607 (9)
H7A	1.1365	0.6356	0.1142	0.073*
H7B	1.1930	0.7063	0.1735	0.073*
C8	0.9236 (4)	0.7269 (2)	0.14806 (14)	0.0458 (8)
H8	0.8879	0.7537	0.1908	0.055*
C9	0.7721 (4)	0.6536 (2)	0.12345 (15)	0.0466 (8)
H9	0.8183	0.6222	0.0832	0.056*
C10	0.7313 (5)	0.5589 (2)	0.16968 (15)	0.0544 (9)
C11	0.6011 (4)	0.7148 (3)	0.10433 (17)	0.0586 (9)
H11A	0.5187	0.6674	0.0819	0.070*
H11B	0.5405	0.7392	0.1434	0.070*
C12	0.6404 (4)	0.8091 (2)	0.06113 (16)	0.0525 (8)
H12A	0.5276	0.8462	0.0525	0.063*
H12B	0.6878	0.7839	0.0200	0.063*
C13	0.7764 (4)	0.8864 (2)	0.09090 (13)	0.0430 (7)
C14	0.9527 (4)	0.8221 (2)	0.10283 (14)	0.0425 (7)
H14	0.9867	0.7924	0.0606	0.051*
C15	1.1112 (4)	0.8932 (3)	0.12316 (17)	0.0586 (9)
H15A	1.0850	0.9252	0.1649	0.070*
H15B	1.2206	0.8510	0.1275	0.070*
C16	1.1409 (5)	0.9786 (3)	0.07313 (18)	0.0631 (10)
H16A	1.2349	1.0265	0.0882	0.076*
H16B	1.1821	0.9467	0.0329	0.076*
C17	0.9700 (5)	1.0397 (3)	0.06076 (18)	0.0609 (9)
H17A	0.9371	1.0783	0.0997	0.073*
H17B	0.9918	1.0908	0.0265	0.073*
N17A	0.8184 (3)	0.97047 (19)	0.04182 (12)	0.0486 (7)
C18	0.6990 (5)	0.9333 (3)	0.15371 (15)	0.0625 (9)
H18A	0.7861	0.9809	0.1724	0.094*
H18B	0.6735	0.8773	0.1838	0.094*
H18C	0.5890	0.9711	0.1442	0.094*
C19	0.6499 (6)	0.5968 (3)	0.23569 (16)	0.0778 (12)
H19A	0.5390	0.6347	0.2279	0.117*
H19B	0.7353	0.6425	0.2571	0.117*
H19C	0.6255	0.5366	0.2627	0.117*
C20	0.6608 (5)	1.0388 (3)	0.02664 (18)	0.0696 (11)
H20A	0.6408	1.0872	0.0625	0.084*
H20B	0.5532	0.9950	0.0223	0.084*
C21	0.6859 (6)	1.1007 (3)	−0.03375 (18)	0.0779 (11)
H21	0.7089	1.0627	−0.0715	0.093*
C22	0.6790 (8)	1.2030 (3)	−0.0389 (3)	0.124 (2)
H22A	0.6564	1.2443	−0.0024	0.148*
H22B	0.6966	1.2350	−0.0791	0.148*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.084 (3)	0.060 (2)	0.099 (3)	−0.019 (2)	−0.013 (2)	0.018 (2)
C2	0.111 (4)	0.062 (3)	0.121 (4)	−0.020 (3)	0.000 (3)	0.016 (3)
C3	0.128 (4)	0.054 (2)	0.071 (3)	0.001 (3)	0.009 (3)	0.0096 (19)
O3	0.189 (4)	0.0567 (16)	0.128 (3)	0.004 (2)	0.002 (3)	0.0110 (17)
C4	0.087 (3)	0.066 (2)	0.059 (2)	0.014 (2)	0.012 (2)	0.0157 (19)
C5	0.066 (2)	0.062 (2)	0.0442 (19)	0.004 (2)	0.0043 (18)	0.0170 (16)
C6	0.064 (2)	0.074 (2)	0.071 (2)	0.008 (2)	−0.009 (2)	0.0214 (19)
C7	0.0471 (19)	0.067 (2)	0.068 (2)	0.0012 (19)	−0.0033 (18)	0.0148 (19)
C8	0.0377 (17)	0.0566 (18)	0.0430 (17)	0.0025 (16)	−0.0006 (14)	0.0029 (15)
C9	0.0436 (19)	0.0506 (17)	0.0455 (16)	0.0000 (17)	0.0010 (15)	0.0017 (14)
C10	0.056 (2)	0.0554 (18)	0.0519 (19)	−0.0034 (19)	0.0068 (17)	0.0035 (16)
C11	0.0433 (19)	0.0593 (19)	0.073 (2)	−0.0074 (17)	−0.0085 (18)	0.0037 (18)
C12	0.0430 (18)	0.0524 (19)	0.062 (2)	0.0019 (16)	−0.0111 (16)	0.0036 (17)
C13	0.0372 (17)	0.0481 (16)	0.0435 (16)	0.0011 (16)	0.0022 (14)	−0.0004 (15)
C14	0.0368 (17)	0.0523 (18)	0.0384 (17)	−0.0015 (15)	−0.0013 (13)	−0.0022 (14)
C15	0.0419 (19)	0.066 (2)	0.068 (2)	−0.0050 (18)	−0.0075 (17)	0.0090 (19)
C16	0.047 (2)	0.061 (2)	0.081 (2)	−0.0127 (19)	0.0003 (17)	0.0054 (19)
C17	0.063 (2)	0.0502 (18)	0.070 (2)	−0.0067 (19)	0.0008 (19)	0.0056 (19)
N17A	0.0450 (15)	0.0427 (13)	0.0582 (15)	0.0050 (14)	−0.0005 (13)	0.0057 (13)
C18	0.060 (2)	0.069 (2)	0.0588 (19)	0.007 (2)	0.0125 (18)	−0.0108 (17)
C19	0.085 (3)	0.077 (2)	0.071 (2)	−0.003 (2)	0.033 (2)	0.015 (2)
C20	0.061 (2)	0.063 (2)	0.085 (3)	0.009 (2)	−0.004 (2)	0.006 (2)
C21	0.088 (3)	0.067 (2)	0.078 (2)	0.023 (2)	−0.013 (2)	0.004 (2)
C22	0.168 (5)	0.071 (3)	0.132 (4)	0.035 (3)	−0.005 (4)	0.031 (3)

Geometric parameters (Å, º) top

C1—C2	1.528 (5)	C12—H12A	0.97
C1—C10	1.532 (5)	C12—H12B	0.97
C1—H1A	0.97	C13—N17A	1.499 (4)
C1—H1B	0.97	C13—C18	1.532 (4)
C2—C3	1.490 (6)	C13—C14	1.550 (4)
C2—H2A	0.97	C14—C15	1.530 (4)
C2—H2B	0.97	C14—H14	0.98
C3—O3	1.215 (4)	C15—C16	1.508 (4)
C3—C4	1.460 (6)	C15—H15A	0.97
C4—C5	1.340 (5)	C15—H15B	0.97
C4—H4	0.93	C16—C17	1.497 (5)
C5—C6	1.500 (5)	C16—H16A	0.97
C5—C10	1.515 (5)	C16—H16B	0.97
C6—C7	1.523 (4)	C17—N17A	1.471 (4)
C6—H6A	0.97	C17—H17A	0.97
C6—H6B	0.97	C17—H17B	0.97
C7—C8	1.532 (4)	N17A—C20	1.479 (4)
C7—H7A	0.97	C18—H18A	0.96
C7—H7B	0.97	C18—H18B	0.96
C8—C9	1.535 (4)	C18—H18C	0.96
C8—C14	1.537 (4)	C19—H19A	0.96
C8—H8	0.98	C19—H19B	0.96
C9—C11	1.529 (4)	C19—H19C	0.96
C9—C10	1.559 (4)	C20—C21	1.481 (5)
C9—H9	0.98	C20—H20A	0.97
C10—C19	1.561 (5)	C20—H20B	0.97
C11—C12	1.515 (4)	C21—C22	1.298 (5)
C11—H11A	0.97	C21—H21	0.93
C11—H11B	0.97	C22—H22A	0.93
C12—C13	1.527 (4)	C22—H22B	0.93

C2—C1—C10	113.8 (4)	C11—C12—H12B	109.0
C2—C1—H1A	108.8	C13—C12—H12B	109.0
C10—C1—H1A	108.8	H12A—C12—H12B	107.8
C2—C1—H1B	108.8	N17A—C13—C12	108.5 (2)
C10—C1—H1B	108.8	N17A—C13—C18	111.8 (2)
H1A—C1—H1B	107.7	C12—C13—C18	110.1 (3)
C3—C2—C1	111.8 (4)	N17A—C13—C14	107.8 (2)
C3—C2—H2A	109.2	C12—C13—C14	106.1 (2)
C1—C2—H2A	109.2	C18—C13—C14	112.3 (2)
C3—C2—H2B	109.2	C15—C14—C8	113.6 (2)
C1—C2—H2B	109.2	C15—C14—C13	112.0 (2)
H2A—C2—H2B	107.9	C8—C14—C13	112.9 (2)
O3—C3—C4	121.8 (5)	C15—C14—H14	105.9
O3—C3—C2	121.5 (5)	C8—C14—H14	105.9
C4—C3—C2	116.7 (3)	C13—C14—H14	105.9
C5—C4—C3	123.8 (4)	C16—C15—C14	110.1 (3)
C5—C4—H4	118.1	C16—C15—H15A	109.6
C3—C4—H4	118.1	C14—C15—H15A	109.6
C4—C5—C6	120.6 (4)	C16—C15—H15B	109.6
C4—C5—C10	122.9 (4)	C14—C15—H15B	109.6
C6—C5—C10	116.5 (3)	H15A—C15—H15B	108.2
C5—C6—C7	114.0 (3)	C17—C16—C15	111.3 (3)
C5—C6—H6A	108.8	C17—C16—H16A	109.4
C7—C6—H6A	108.8	C15—C16—H16A	109.4
C5—C6—H6B	108.8	C17—C16—H16B	109.4
C7—C6—H6B	108.8	C15—C16—H16B	109.4
H6A—C6—H6B	107.7	H16A—C16—H16B	108.0
C6—C7—C8	111.4 (3)	N17A—C17—C16	112.1 (3)
C6—C7—H7A	109.3	N17A—C17—H17A	109.2
C8—C7—H7A	109.3	C16—C17—H17A	109.2
C6—C7—H7B	109.3	N17A—C17—H17B	109.2
C8—C7—H7B	109.3	C16—C17—H17B	109.2
H7A—C7—H7B	108.0	H17A—C17—H17B	107.9
C7—C8—C9	108.5 (2)	C17—N17A—C20	107.7 (2)
C7—C8—C14	111.9 (2)	C17—N17A—C13	113.5 (2)
C9—C8—C14	111.9 (2)	C20—N17A—C13	113.3 (2)
C7—C8—H8	108.1	C13—C18—H18A	109.5
C9—C8—H8	108.1	C13—C18—H18B	109.5
C14—C8—H8	108.1	H18A—C18—H18B	109.5
C11—C9—C8	112.2 (2)	C13—C18—H18C	109.5
C11—C9—C10	112.8 (3)	H18A—C18—H18C	109.5
C8—C9—C10	113.7 (3)	H18B—C18—H18C	109.5
C11—C9—H9	105.8	C10—C19—H19A	109.5
C8—C9—H9	105.8	C10—C19—H19B	109.5
C10—C9—H9	105.8	H19A—C19—H19B	109.5
C5—C10—C1	109.6 (3)	C10—C19—H19C	109.5
C5—C10—C9	109.2 (3)	H19A—C19—H19C	109.5
C1—C10—C9	109.2 (3)	H19B—C19—H19C	109.5
C5—C10—C19	107.5 (3)	N17A—C20—C21	112.8 (3)
C1—C10—C19	109.5 (3)	N17A—C20—H20A	109.0
C9—C10—C19	111.7 (2)	C21—C20—H20A	109.0
C12—C11—C9	113.0 (3)	N17A—C20—H20B	109.0
C12—C11—H11A	109.0	C21—C20—H20B	109.0
C9—C11—H11A	109.0	H20A—C20—H20B	107.8
C12—C11—H11B	109.0	C22—C21—C20	126.2 (4)
C9—C11—H11B	109.0	C22—C21—H21	116.9
H11A—C11—H11B	107.8	C20—C21—H21	116.9
C11—C12—C13	113.1 (3)	C21—C22—H22A	120.0
C11—C12—H12A	109.0	C21—C22—H22B	120.0
C13—C12—H12A	109.0	H22A—C22—H22B	120.0

C10—C1—C2—C3	−53.3 (5)	C9—C11—C12—C13	−56.0 (3)
C1—C2—C3—O3	−153.6 (4)	C11—C12—C13—N17A	174.7 (2)
C1—C2—C3—C4	29.3 (6)	C11—C12—C13—C18	−62.6 (3)
O3—C3—C4—C5	−177.8 (4)	C11—C12—C13—C14	59.1 (3)
C2—C3—C4—C5	−0.8 (6)	C7—C8—C14—C15	−54.1 (3)
C3—C4—C5—C6	171.3 (3)	C9—C8—C14—C15	−176.1 (3)
C3—C4—C5—C10	−5.1 (6)	C7—C8—C14—C13	177.1 (3)
C4—C5—C6—C7	136.2 (3)	C9—C8—C14—C13	55.0 (3)
C10—C5—C6—C7	−47.2 (4)	N17A—C13—C14—C15	55.3 (3)
C5—C6—C7—C8	51.6 (4)	C12—C13—C14—C15	171.4 (2)
C6—C7—C8—C9	−56.7 (3)	C18—C13—C14—C15	−68.3 (3)
C6—C7—C8—C14	179.4 (3)	N17A—C13—C14—C8	−175.0 (2)
C7—C8—C9—C11	−171.6 (3)	C12—C13—C14—C8	−58.9 (3)
C14—C8—C9—C11	−47.7 (3)	C18—C13—C14—C8	61.4 (3)
C7—C8—C9—C10	59.0 (3)	C8—C14—C15—C16	174.9 (3)
C14—C8—C9—C10	−177.1 (2)	C13—C14—C15—C16	−55.8 (3)
C4—C5—C10—C1	−17.9 (5)	C14—C15—C16—C17	54.4 (4)
C6—C5—C10—C1	165.5 (3)	C15—C16—C17—N17A	−55.3 (4)
C4—C5—C10—C9	−137.5 (3)	C16—C17—N17A—C20	−176.3 (3)
C6—C5—C10—C9	45.9 (4)	C16—C17—N17A—C13	57.4 (3)
C4—C5—C10—C19	101.1 (4)	C12—C13—N17A—C17	−170.5 (2)
C6—C5—C10—C19	−75.5 (3)	C18—C13—N17A—C17	67.9 (3)
C2—C1—C10—C5	46.5 (5)	C14—C13—N17A—C17	−56.0 (3)
C2—C1—C10—C9	166.1 (3)	C12—C13—N17A—C20	66.3 (3)
C2—C1—C10—C19	−71.2 (4)	C18—C13—N17A—C20	−55.3 (3)
C11—C9—C10—C5	178.2 (3)	C14—C13—N17A—C20	−179.2 (2)
C8—C9—C10—C5	−52.6 (3)	C17—N17A—C20—C21	69.7 (4)
C11—C9—C10—C1	58.4 (3)	C13—N17A—C20—C21	−163.9 (3)
C8—C9—C10—C1	−172.5 (3)	N17A—C20—C21—C22	−122.6 (5)
C11—C9—C10—C19	−62.9 (4)	H14—C14—C13—C18	176.8
C8—C9—C10—C19	66.2 (4)	H8—C8—C9—H9	−173.8
C8—C9—C11—C12	48.3 (4)	H9—C9—C10—C19	−178.1
C10—C9—C11—C12	178.2 (3)	C19—C10—C13—C18	0.4 (3)

Experimental details

Crystal data
Chemical formula	C₂₂H₃₃NO
M_r	327.49
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	7.358 (2), 12.635 (2), 20.596 (10)
V (Å³)	1914.8 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.20 × 0.17 × 0.17

Data collection
Diffractometer	Enraf-Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	1992, 1910, 1228
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.120, 1.03
No. of reflections	1910
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.15

Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1994), CAD-4 EXPRESS, MolEN (Fair, 1990), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP97 (Zsolnai, 1997), SHELXL97.

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