3-Isopropyl-2,6-bis­(4-meth­oxy­phen­yl)­piperidin-4-one

Ravichandran, K.; Sethuvasan, S.; Thirunavukarasu, K.; Ponnuswamy, S.; Ponnuswamy, M.N.

doi:10.1107/S1600536812030966

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2453

https://doi.org/10.1107/S1600536812030966

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3-Isopropyl-2,6-bis(4-methoxyphenyl)piperidin-4-one

K. Ravichandran,^a S. Sethuvasan,^b K. Thirunavukarasu,^b S. Ponnuswamy ^b ^* and M. N. Ponnuswamy ^a

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Chemistry, Government Arts College (Autonomous), Coimbatore 641 018, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

(Received 18 May 2012; accepted 6 July 2012; online 14 July 2012)

In the title compound, C₂₂H₂₇NO₃, the piperidine ring adopts a slightly distorted chair conformation. The dihedral angle between the two aromatic rings is 60.4 (1)°. In the crystal, the amino group forms a rather long N—H⋯O contact to a methoxy O atom. There are also C—H⋯O interactions present.

Related literature

For the biological activity of piperidine derivatives, see: Bochringer & Soehne (1961 ); El-Subbagh et al. (2000 ); Ganellin & Spickett (1965 ); Hagenbach & Gysin (1952 ); Jerom & Spencer (1988 ); Katritzky & Fan (1990 ); Perumal et al. (2001 ); Ravindran et al. (1991 ); Severs et al. (1965 ). For puckering parameters, see: Cremer & Pople (1975 ). For asymmetry parameters, see: Nardelli (1983 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₂H₂₇NO₃
M_r = 353.45
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.5547 (3) Å
b = 11.8792 (6) Å
c = 22.1103 (10) Å
V = 1984.26 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.983, T_max = 0.986
10956 measured reflections
2801 independent reflections
1835 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.121
S = 1.03
2801 reflections
241 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.90 (2)	2.66 (2)	3.538 (2)	167.4 (17)
C16—H16A⋯O1ⁱⁱ	0.96	2.57	3.474 (4)	156
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812030966/bt5928sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812030966/bt5928Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812030966/bt5928Isup3.cml

checkCIF report

Comment top

In the family of heterocyclic compounds, piperidin-4-ones possess varied biological properties such as antiviral, antitumour (El-Subbagh et al., 2000), analgesic (Jerom & Spencer, 1988), local anaesthetic (Perumal et al., 2001; Hagenbach & Gysin, 1952), anti-inflammatory and anticancer activities (Katritzky & Fan, 1990). Several 2,6-disubstituted piperidines are found to be useful as tranquillisers (Bochringer & Soehne, 1961) and possess hypotensive activity (Severs et al., 1965), a combination of stimulant and depressant effects on the central nervous system (Ganellin & Spickett, 1965). Also the substitution of methoxy phenyl groups at 2,6-positions is found to be active against CNS subpanels. In addition, the bulkiness of the subtituent in different positons of the piperidine ring leads to the decrease in carcinogenecity (Ravindran et al., 1991). In view of the importance, the crystallographic study of the title compound has been carried out to establish the molecular structure and conformation.

The ORTEP plot of the molecule is shown in Fig. 1. The piperidine ring adopts distorted chair conformation. The puckering (Cremer & Pople, 1975) and the asymmetry parameters (Nardelli, 1983) are: q₂=0.121 (3) Å, q₃ = 0.569 (3) Å, φ₂ = 7.6 (1)° and Δ_s(N1 & C4) = 1.3 (2)°. The sum of the bond angles around the atom N1 [333.5°] is in accordance with sp³ hybridization.

The best plane of the piperidine ring is oriented with respect to the phenyl rings (C9—C14) & (C18—C23) at angles of 82.8 (1)° & 86.2 (1)°, respectively. The two phenyl rings are set apart with an angle of 60.4 (1)°. The methoxy groups substituted at the phenyl rings are coplanar, which can be seen from the torsion angles of [C13—C12—O1—C7=] 4.4 (4)° for (C9—C14) ring and [C20—C21—O3—C8 =] 1.6 (5)° for (C18—C23) ring.

The packing of the molecules is stabilized by a rather long N-H···O contact and by C—H···O interactions in addition to van der Waals forces.

Related literature top

For the biological activity of piperidine derivatives, see: Bochringer & Soehne (1961); El-Subbagh et al. (2000); Ganellin & Spickett (1965); Hagenbach & Gysin (1952); Jerom & Spencer (1988); Katritzky & Fan (1990); Perumal et al. (2001); Ravindran et al. (1991); Severs et al.(1965). For puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Nardelli (1983). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

Ammonium acetate (100 mmol), anisaldehyde (200 mmol) and isobutylmethylketone (100 mmol) in ethanol (30 ml) were heated on a hot plate at 50–55° C and after the completion of reaction, water was added and extracted with ether, dried and recrystallized from ethanol.

Structure description top

The packing of the molecules is stabilized by a rather long N-H···O contact and by C—H···O interactions in addition to van der Waals forces.

For the biological activity of piperidine derivatives, see: Bochringer & Soehne (1961); El-Subbagh et al. (2000); Ganellin & Spickett (1965); Hagenbach & Gysin (1952); Jerom & Spencer (1988); Katritzky & Fan (1990); Perumal et al. (2001); Ravindran et al. (1991); Severs et al.(1965). For puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Nardelli (1983). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atomic numbering and displacement ellipsoids drawn at 30% probability level.
	Fig. 2. The crystal packing of the molecules viewed down b axis. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

3-Isopropyl-2,6-bis(4-methoxyphenyl)piperidin-4-one top

Crystal data top

C₂₂H₂₇NO₃	F(000) = 760
M_r = 353.45	D_x = 1.183 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2938 reflections
a = 7.5547 (3) Å	θ = 1.8–28.3°
b = 11.8792 (6) Å	µ = 0.08 mm⁻¹
c = 22.1103 (10) Å	T = 293 K
V = 1984.26 (16) Å³	Black, white crystalline
Z = 4	0.22 × 0.20 × 0.18 mm

Data collection top

Bruker SMART APEX CCD detector diffractometer	2801 independent reflections
Radiation source: fine-focus sealed tube	1835 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 28.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→9
T_min = 0.983, T_max = 0.986	k = −15→8
10956 measured reflections	l = −27→29

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0621P)² + 0.0599P] where P = (F_o² + 2F_c²)/3
2801 reflections	(Δ/σ)_max = 0.015
241 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₂₂H₂₇NO₃	V = 1984.26 (16) Å³
M_r = 353.45	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.5547 (3) Å	µ = 0.08 mm⁻¹
b = 11.8792 (6) Å	T = 293 K
c = 22.1103 (10) Å	0.22 × 0.20 × 0.18 mm

Data collection top

Bruker SMART APEX CCD detector diffractometer	2801 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	1835 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.986	R_int = 0.038
10956 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.17 e Å⁻³
2801 reflections	Δρ_min = −0.13 e Å⁻³
241 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
H1	0.161 (4)	0.568 (2)	0.1225 (11)	0.049 (7)*
O1	0.3703 (3)	0.80940 (17)	−0.10981 (8)	0.0655 (6)
O2	0.6143 (3)	0.2871 (2)	0.15552 (10)	0.0773 (7)
O3	−0.2117 (3)	0.5919 (2)	0.37078 (10)	0.0865 (8)
N1	0.2620 (3)	0.53392 (18)	0.13369 (9)	0.0446 (5)
C2	0.3533 (3)	0.4891 (2)	0.08036 (10)	0.0433 (6)
H2	0.2910	0.4212	0.0669	0.052*
C3	0.5444 (3)	0.4554 (2)	0.09959 (11)	0.0451 (6)
H3	0.5993	0.5241	0.1155	0.054*
C4	0.5323 (4)	0.3749 (3)	0.15235 (13)	0.0556 (7)
C5	0.4118 (4)	0.4096 (3)	0.20247 (12)	0.0676 (9)
H5A	0.4656	0.4711	0.2247	0.081*
H5B	0.3966	0.3470	0.2302	0.081*
C6	0.2300 (3)	0.4469 (2)	0.17908 (12)	0.0507 (6)
H6	0.1737	0.3825	0.1592	0.061*
C7	0.3092 (5)	0.7822 (3)	−0.16890 (12)	0.0731 (9)
H7A	0.3785	0.7215	−0.1850	0.110*
H7B	0.3206	0.8469	−0.1946	0.110*
H7C	0.1872	0.7599	−0.1670	0.110*
C8	−0.3714 (6)	0.5342 (4)	0.38404 (18)	0.1054 (14)
H8A	−0.4477	0.5363	0.3493	0.158*
H8B	−0.4292	0.5699	0.4176	0.158*
H8C	−0.3453	0.4574	0.3941	0.158*
C9	0.3520 (3)	0.5733 (2)	0.02940 (10)	0.0413 (5)
C10	0.4059 (3)	0.6843 (2)	0.03831 (12)	0.0508 (6)
H10	0.4390	0.7076	0.0768	0.061*
C11	0.4112 (4)	0.7599 (2)	−0.00879 (13)	0.0555 (7)
H11	0.4486	0.8333	−0.0019	0.067*
C12	0.3614 (3)	0.7275 (2)	−0.06612 (11)	0.0470 (6)
C13	0.3080 (4)	0.6181 (2)	−0.07623 (11)	0.0518 (7)
H13	0.2749	0.5950	−0.1148	0.062*
C14	0.3041 (3)	0.5433 (2)	−0.02846 (11)	0.0493 (6)
H14	0.2676	0.4697	−0.0357	0.059*
C15	0.6625 (3)	0.4165 (2)	0.04695 (12)	0.0470 (6)
H15	0.6556	0.4757	0.0162	0.056*
C16	0.8571 (3)	0.4099 (3)	0.06599 (13)	0.0578 (7)
H16A	0.8910	0.4792	0.0851	0.087*
H16B	0.9296	0.3976	0.0309	0.087*
H16C	0.8728	0.3488	0.0939	0.087*
C17	0.6047 (4)	0.3087 (3)	0.01612 (14)	0.0691 (8)
H17A	0.4828	0.3150	0.0043	0.104*
H17B	0.6181	0.2467	0.0436	0.104*
H17C	0.6765	0.2961	−0.0191	0.104*
C18	0.1107 (3)	0.4866 (2)	0.22900 (11)	0.0489 (6)
C19	−0.0469 (3)	0.4320 (2)	0.24044 (12)	0.0521 (6)
H19	−0.0796	0.3720	0.2159	0.063*
C20	−0.1579 (4)	0.4634 (3)	0.28710 (12)	0.0577 (7)
H20	−0.2627	0.4243	0.2939	0.069*
C21	−0.1124 (4)	0.5531 (3)	0.32367 (12)	0.0579 (7)
C22	0.0451 (4)	0.6089 (3)	0.31305 (13)	0.0625 (8)
H22	0.0774	0.6689	0.3377	0.075*
C23	0.1547 (4)	0.5767 (2)	0.26643 (13)	0.0577 (7)
H23	0.2597	0.6156	0.2598	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0953 (15)	0.0511 (11)	0.0502 (11)	−0.0043 (11)	0.0027 (10)	0.0050 (9)
O2	0.0696 (13)	0.0697 (14)	0.0927 (15)	0.0253 (12)	0.0052 (11)	0.0272 (12)
O3	0.0879 (16)	0.1049 (19)	0.0665 (14)	−0.0023 (15)	0.0205 (12)	−0.0176 (13)
N1	0.0394 (10)	0.0469 (13)	0.0475 (12)	0.0030 (10)	−0.0020 (9)	0.0051 (10)
C2	0.0364 (10)	0.0433 (14)	0.0503 (13)	−0.0006 (10)	−0.0025 (10)	0.0002 (11)
C3	0.0401 (11)	0.0420 (14)	0.0532 (14)	0.0022 (10)	−0.0056 (11)	0.0021 (13)
C4	0.0427 (13)	0.0603 (18)	0.0638 (17)	0.0085 (13)	−0.0080 (12)	0.0113 (15)
C5	0.0638 (17)	0.085 (2)	0.0543 (16)	0.0188 (17)	−0.0014 (14)	0.0201 (16)
C6	0.0504 (13)	0.0529 (16)	0.0487 (14)	0.0018 (12)	0.0016 (11)	0.0082 (13)
C7	0.108 (2)	0.068 (2)	0.0435 (16)	0.0003 (19)	0.0086 (17)	0.0070 (15)
C8	0.096 (3)	0.137 (4)	0.083 (2)	−0.012 (3)	0.038 (2)	−0.014 (2)
C9	0.0333 (10)	0.0407 (14)	0.0499 (14)	0.0004 (10)	−0.0019 (10)	−0.0008 (11)
C10	0.0588 (15)	0.0479 (16)	0.0457 (14)	−0.0043 (13)	−0.0080 (12)	−0.0018 (13)
C11	0.0693 (17)	0.0400 (15)	0.0572 (16)	−0.0103 (13)	−0.0047 (14)	−0.0029 (13)
C12	0.0519 (13)	0.0414 (16)	0.0478 (14)	0.0024 (12)	0.0057 (11)	0.0012 (12)
C13	0.0661 (16)	0.0472 (16)	0.0420 (14)	0.0008 (12)	−0.0071 (12)	−0.0036 (12)
C14	0.0567 (14)	0.0383 (14)	0.0529 (15)	−0.0021 (11)	−0.0056 (12)	−0.0028 (12)
C15	0.0413 (11)	0.0454 (14)	0.0543 (14)	0.0048 (11)	−0.0024 (11)	−0.0031 (12)
C16	0.0431 (13)	0.0596 (18)	0.0706 (18)	0.0027 (12)	−0.0004 (13)	−0.0089 (15)
C17	0.0547 (16)	0.0677 (19)	0.085 (2)	0.0008 (15)	−0.0062 (15)	−0.0205 (17)
C18	0.0478 (13)	0.0529 (16)	0.0461 (13)	0.0025 (12)	−0.0039 (11)	0.0104 (13)
C19	0.0509 (13)	0.0556 (16)	0.0498 (14)	−0.0027 (13)	−0.0045 (12)	0.0008 (13)
C20	0.0513 (13)	0.073 (2)	0.0485 (14)	−0.0068 (14)	0.0014 (12)	0.0042 (14)
C21	0.0625 (15)	0.0669 (19)	0.0443 (14)	0.0046 (14)	0.0016 (13)	0.0002 (14)
C22	0.0728 (18)	0.0581 (19)	0.0566 (17)	−0.0064 (15)	−0.0047 (15)	−0.0039 (15)
C23	0.0561 (15)	0.0556 (17)	0.0615 (17)	−0.0095 (14)	−0.0029 (13)	0.0068 (14)

Geometric parameters (Å, º) top

O1—C12	1.373 (3)	C10—C11	1.376 (4)
O1—C7	1.423 (3)	C10—H10	0.9300
O2—C4	1.215 (3)	C11—C12	1.377 (4)
O3—C21	1.364 (3)	C11—H11	0.9300
O3—C8	1.419 (5)	C12—C13	1.379 (4)
N1—C6	1.461 (3)	C13—C14	1.381 (4)
N1—C2	1.466 (3)	C13—H13	0.9300
N1—H1	0.90 (3)	C14—H14	0.9300
C2—C9	1.507 (3)	C15—C17	1.515 (4)
C2—C3	1.557 (3)	C15—C16	1.531 (3)
C2—H2	0.9800	C15—H15	0.9800
C3—C4	1.512 (4)	C16—H16A	0.9600
C3—C15	1.538 (3)	C16—H16B	0.9600
C3—H3	0.9800	C16—H16C	0.9600
C4—C5	1.493 (4)	C17—H17A	0.9600
C5—C6	1.533 (4)	C17—H17B	0.9600
C5—H5A	0.9700	C17—H17C	0.9600
C5—H5B	0.9700	C18—C19	1.380 (4)
C6—C18	1.501 (4)	C18—C23	1.392 (4)
C6—H6	0.9800	C19—C20	1.381 (4)
C7—H7A	0.9600	C19—H19	0.9300
C7—H7B	0.9600	C20—C21	1.382 (4)
C7—H7C	0.9600	C20—H20	0.9300
C8—H8A	0.9600	C21—C22	1.382 (4)
C8—H8B	0.9600	C22—C23	1.377 (4)
C8—H8C	0.9600	C22—H22	0.9300
C9—C14	1.377 (3)	C23—H23	0.9300
C9—C10	1.393 (4)

C12—O1—C7	118.0 (2)	C9—C10—H10	119.4
C21—O3—C8	117.5 (3)	C10—C11—C12	120.4 (3)
C6—N1—C2	111.9 (2)	C10—C11—H11	119.8
C6—N1—H1	111.7 (16)	C12—C11—H11	119.8
C2—N1—H1	109.9 (16)	O1—C12—C11	115.9 (2)
N1—C2—C9	110.95 (19)	O1—C12—C13	124.6 (2)
N1—C2—C3	108.06 (19)	C11—C12—C13	119.5 (2)
C9—C2—C3	112.40 (18)	C12—C13—C14	119.3 (2)
N1—C2—H2	108.4	C12—C13—H13	120.4
C9—C2—H2	108.4	C14—C13—H13	120.4
C3—C2—H2	108.4	C9—C14—C13	122.6 (2)
C4—C3—C15	115.4 (2)	C9—C14—H14	118.7
C4—C3—C2	108.5 (2)	C13—C14—H14	118.7
C15—C3—C2	114.1 (2)	C17—C15—C16	111.0 (2)
C4—C3—H3	106.0	C17—C15—C3	115.3 (2)
C15—C3—H3	106.0	C16—C15—C3	111.4 (2)
C2—C3—H3	106.0	C17—C15—H15	106.2
O2—C4—C5	120.4 (3)	C16—C15—H15	106.2
O2—C4—C3	123.9 (3)	C3—C15—H15	106.2
C5—C4—C3	115.8 (2)	C15—C16—H16A	109.5
C4—C5—C6	112.1 (2)	C15—C16—H16B	109.5
C4—C5—H5A	109.2	H16A—C16—H16B	109.5
C6—C5—H5A	109.2	C15—C16—H16C	109.5
C4—C5—H5B	109.2	H16A—C16—H16C	109.5
C6—C5—H5B	109.2	H16B—C16—H16C	109.5
H5A—C5—H5B	107.9	C15—C17—H17A	109.5
N1—C6—C18	112.5 (2)	C15—C17—H17B	109.5
N1—C6—C5	106.8 (2)	H17A—C17—H17B	109.5
C18—C6—C5	112.4 (2)	C15—C17—H17C	109.5
N1—C6—H6	108.4	H17A—C17—H17C	109.5
C18—C6—H6	108.4	H17B—C17—H17C	109.5
C5—C6—H6	108.4	C19—C18—C23	117.3 (2)
O1—C7—H7A	109.5	C19—C18—C6	120.4 (2)
O1—C7—H7B	109.5	C23—C18—C6	122.4 (2)
H7A—C7—H7B	109.5	C18—C19—C20	122.3 (3)
O1—C7—H7C	109.5	C18—C19—H19	118.9
H7A—C7—H7C	109.5	C20—C19—H19	118.9
H7B—C7—H7C	109.5	C19—C20—C21	119.6 (3)
O3—C8—H8A	109.5	C19—C20—H20	120.2
O3—C8—H8B	109.5	C21—C20—H20	120.2
H8A—C8—H8B	109.5	O3—C21—C22	116.2 (3)
O3—C8—H8C	109.5	O3—C21—C20	124.8 (3)
H8A—C8—H8C	109.5	C22—C21—C20	119.0 (3)
H8B—C8—H8C	109.5	C23—C22—C21	120.8 (3)
C14—C9—C10	117.0 (2)	C23—C22—H22	119.6
C14—C9—C2	121.6 (2)	C21—C22—H22	119.6
C10—C9—C2	121.3 (2)	C22—C23—C18	121.0 (3)
C11—C10—C9	121.3 (2)	C22—C23—H23	119.5
C11—C10—H10	119.4	C18—C23—H23	119.5

C6—N1—C2—C9	168.49 (19)	C10—C11—C12—C13	−0.7 (4)
C6—N1—C2—C3	−67.9 (2)	O1—C12—C13—C14	−179.8 (2)
N1—C2—C3—C4	54.9 (3)	C11—C12—C13—C14	0.5 (4)
C9—C2—C3—C4	177.7 (2)	C10—C9—C14—C13	−0.1 (4)
N1—C2—C3—C15	−174.9 (2)	C2—C9—C14—C13	−177.6 (2)
C9—C2—C3—C15	−52.1 (3)	C12—C13—C14—C9	−0.1 (4)
C15—C3—C4—O2	3.0 (4)	C4—C3—C15—C17	61.6 (3)
C2—C3—C4—O2	132.5 (3)	C2—C3—C15—C17	−65.1 (3)
C15—C3—C4—C5	−177.4 (2)	C4—C3—C15—C16	−66.0 (3)
C2—C3—C4—C5	−47.9 (3)	C2—C3—C15—C16	167.3 (2)
O2—C4—C5—C6	−131.9 (3)	N1—C6—C18—C19	120.8 (3)
C3—C4—C5—C6	48.5 (4)	C5—C6—C18—C19	−118.7 (3)
C2—N1—C6—C18	−170.4 (2)	N1—C6—C18—C23	−61.0 (3)
C2—N1—C6—C5	65.9 (3)	C5—C6—C18—C23	59.5 (3)
C4—C5—C6—N1	−53.8 (3)	C23—C18—C19—C20	−0.5 (4)
C4—C5—C6—C18	−177.6 (3)	C6—C18—C19—C20	177.9 (2)
N1—C2—C9—C14	−131.8 (2)	C18—C19—C20—C21	0.7 (4)
C3—C2—C9—C14	107.1 (3)	C8—O3—C21—C22	−178.0 (3)
N1—C2—C9—C10	50.7 (3)	C8—O3—C21—C20	1.6 (5)
C3—C2—C9—C10	−70.4 (3)	C19—C20—C21—O3	179.7 (3)
C14—C9—C10—C11	−0.2 (4)	C19—C20—C21—C22	−0.8 (4)
C2—C9—C10—C11	177.4 (2)	O3—C21—C22—C23	−179.7 (3)
C9—C10—C11—C12	0.6 (4)	C20—C21—C22—C23	0.7 (4)
C7—O1—C12—C11	−175.9 (3)	C21—C22—C23—C18	−0.5 (4)
C7—O1—C12—C13	4.4 (4)	C19—C18—C23—C22	0.4 (4)
C10—C11—C12—O1	179.6 (2)	C6—C18—C23—C22	−177.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.90 (2)	2.66 (2)	3.538 (2)	167.4 (17)
C16—H16A···O1ⁱⁱ	0.96	2.57	3.474 (4)	156

Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x+1/2, −y+3/2, −z.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₇NO₃
M_r	353.45
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	7.5547 (3), 11.8792 (6), 22.1103 (10)
V (Å³)	1984.26 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD detector
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.983, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	10956, 2801, 1835
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.121, 1.03
No. of reflections	2801
No. of parameters	241
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.13

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.90 (2)	2.66 (2)	3.538 (2)	167.4 (17)
C16—H16A···O1ⁱⁱ	0.96	2.57	3.474 (4)	156.0

Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x+1/2, −y+3/2, −z.

Acknowledgements

KR thanks the TBI Consultancy, University of Madras, India, for the data collection and the management of Kandaswami Kandar's College, Velur, Namakkal, Tamilnadu, India, for the encouragement. SP thanks UGC, New Delhi, for financial assistance in the form of a major research project.

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