2,4-Bis(2-methoxy­phenyl)-3-aza­bicyclo­[3.3.1]nonan-9-one

Parthiban, P.; Ramkumar, V.; Kim, M.S.; Son, S.M.; Jeong, Y.T.

doi:10.1107/S1600536809018686

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1383

doi:10.1107/S1600536809018686

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2,4-Bis(2-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one

P. Parthiban,^a V. Ramkumar,^b Min Sung Kim,^a Se Mo Son ^a and Yeon Tae Jeong ^a ^*

^aDivision of Image Science and Information Engineering, Pukyong National University, Busan 608 739, Republic of Korea, and ^bDepartment of Chemistry, IIT Madras, Chennai 36, Tamil Nadu, India
^*Correspondence e-mail: ytjeong@pknu.ac.kr

(Received 27 April 2009; accepted 18 May 2009; online 23 May 2009)

In the title compound, C₂₂H₂₅NO₃, the molecule has a pseudo-mirror plane. The structure is a positional isomer of 2,4-bis(4-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one [Cox, McCabe, Milne & Sim (1985 ). J. Chem. Soc. Chem. Commun. pp. 626–628]. The 3-azabicyclo[3.3.1]nonan-9-one moiety adopts a double chair conformation with equatorial orientations of both 2-methoxyphenyl substituents on either side of the secondary amino group. The benzene rings are oriented at an angle of 33.86 (4)° with respect to each other and the methoxy groups point towards the carbonyl group. The crystal structure is stabilized by intermolecular N—H⋯π interactions.

Related literature

For prevalence and biological activities of 3-azabicyclononan-9-ones, see: Hardick et al. (1996 ); Jeyaraman & Avila (1981 ); Barker et al. (2005 ). For similiar structures, see: Parthiban et al. (2008a ,b ); Cox et al. (1985). For ring-puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₂H₂₅NO₃
M_r = 351.43
Monoclinic, P 2₁ /n
a = 7.8616 (2) Å
b = 20.8443 (6) Å
c = 11.4984 (3) Å
β = 95.670(10)°
V = 1874.37 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.58 × 0.42 × 0.35 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.945, T_max = 0.972
14712 measured reflections
4527 independent reflections
3202 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.135
S = 1.03
4527 reflections
241 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
N—H⋯π geometry (Å, ° )

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cg1ⁱ	0.90 (4)	2.75 (4)	3.58 (5)	152.87 (3)
Symmetry code: (i) -x+1, -y+2, -z. Cg1 is the centroid of the C9–C14 ring.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker, 2004); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018686/bx2207sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809018686/bx2207Isup2.hkl

checkCIF report

Comment top

Widespread interest in the chemistry of 3-azabicyclononan-9-ones is due to their presence in numerous naturally occurring alkaloids and broad spectrum biological activities (Jeyaraman & Avila, 1981; Hardick et al., 1996; Barker et al., 2005). Since the stereochemistry plays a crucial role in eliciting the biological response, it is immense to establish the stereochemistry of the biologically important molecules. Even though similar compounds show double chair conformation (Parthiban et al., 2008a,b), we have carried out the single-crystal XRD study for the title compound to know the impact of comparatively bulkier methoxy substituent on ortho position of the phenyl group, attached on either side of the secondary amino group.The molecule has a pseudo mirror plane.The structure is a positional isomer of 2,4-Bis(p-methoxyphenyl)-3-azabicyclo(3.3.1)nonan-9-one (Cox et al., 1985). The title compound C₂₂H₂₅NO₃, exists in double chair conformation with an equatorial orientation of the ortho-methoxyphenyl group on both sides of the secondary amino group with the torsion angle of C8—C2—C1—C9 and C8—C6—C7—C15 are -179.66 (3) and -179.76 (4)°, respectively. In both aryl groups, the methoxy substituent point towards the carbonyl group at an angle of 33.86 (4)° to each other. A study of torsion angles, asymmetry parameters and least-squares plane calculation shows that the piperidine ring adopts near ideal chair conformation with the deviation of ring atoms N1 and C8 from the C1/C2/C6/C7 plane by -0.641 (3) and 0.718 (3) Å, respectively; Q_T = 0.6101 (15) Å, q(2)= 0.0490 (15) Å, q(3)= -0.6081 (15) Å, θ = 175.41 (14)° (Cremer & Pople, 1975) whereas the cyclohexane ring atoms C4 and C8 deviate from the C2/C3/C5/C6 plane by -0.537 (4) and 0.710 (3) Å, respectively; Q_T = 0.5528 (17) Å, q(2)= 0.1286 (17) Å, q(3)= -0.5376 (17) Å, θ = 166.55 (18)°.

Related literature top

For prevalence and biological activities of 3-azabicyclononan-9-ones, see: Hardick et al. (1996); Jeyaraman & Avila (1981); Barker et al. (2005). For similiar structures, see: Parthiban et al. (2008a,b); Cox et al. (1985). For ring-puckering parameters, see: Cremer & Pople (1975). [Please check amended text]

Experimental top

A mixture of cyclohexanone (4.90 g) and ortho-methoxybenzaldehyde (13.62 g) was added to a warm solution of ammonium acetate (5.78 g) in 50 ml of absolute ethanol. The mixture was gently warmed with stirring till the yellow color was formed during the mixing of the reactants and then allowed to stirring at room temperature up to the formation of product. At the end, the crude azabicyclic ketone was separated by filtration and washed with 1:5 ethanol–ether mixture till the solid became colorless. Recrystallization of the compound from ethanol gave X-ray diffraction quality crystals of 2,4-bis(2-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); 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).

Figures top

	Fig. 1. View of the title molecule with atoms represented as 30% probability ellipsoids.
	Fig. 2. The N—H···π interactions.

2,4-Bis(2-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one top

Crystal data top

C₂₂H₂₅NO₃	F(000) = 752
M_r = 351.43	D_x = 1.245 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4251 reflections
a = 7.8616 (2) Å	θ = 2.6–27.0°
b = 20.8443 (6) Å	µ = 0.08 mm⁻¹
c = 11.4984 (3) Å	T = 298 K
β = 95.867 (1)°	Block, colourless
V = 1874.37 (9) Å³	0.58 × 0.42 × 0.35 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	4527 independent reflections
Radiation source: fine-focus sealed tube	3202 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −9→10
T_min = 0.945, T_max = 0.972	k = −27→26
14712 measured reflections	l = −15→13

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.065P)² + 0.3026P] where P = (F_o² + 2F_c²)/3
4527 reflections	(Δ/σ)_max = 0.001
241 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₂H₂₅NO₃	V = 1874.37 (9) Å³
M_r = 351.43	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.8616 (2) Å	µ = 0.08 mm⁻¹
b = 20.8443 (6) Å	T = 298 K
c = 11.4984 (3) Å	0.58 × 0.42 × 0.35 mm
β = 95.867 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4527 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	3202 reflections with I > 2σ(I)
T_min = 0.945, T_max = 0.972	R_int = 0.023
14712 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.17 e Å⁻³
4527 reflections	Δρ_min = −0.25 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
C1	0.72892 (16)	0.98913 (6)	0.17176 (12)	0.0343 (3)
H1	0.7974	0.9851	0.1055	0.041*
C2	0.85201 (18)	1.00058 (7)	0.28460 (14)	0.0417 (3)
H2	0.9208	1.0389	0.2735	0.050*
C3	0.7636 (2)	1.00894 (8)	0.39684 (15)	0.0531 (4)
H3A	0.8479	1.0232	0.4589	0.064*
H3B	0.6781	1.0424	0.3840	0.064*
C4	0.6779 (2)	0.94870 (9)	0.43724 (15)	0.0582 (4)
H4A	0.5702	0.9424	0.3894	0.070*
H4B	0.6529	0.9545	0.5175	0.070*
C5	0.7881 (2)	0.88909 (8)	0.42979 (15)	0.0552 (4)
H5A	0.7179	0.8515	0.4390	0.066*
H5B	0.8775	0.8896	0.4945	0.066*
C6	0.87146 (18)	0.88257 (7)	0.31544 (14)	0.0435 (4)
H6	0.9521	0.8466	0.3229	0.052*
C7	0.74651 (17)	0.87292 (6)	0.20328 (13)	0.0366 (3)
H7	0.8145	0.8689	0.1368	0.044*
C8	0.96882 (18)	0.94334 (7)	0.29817 (14)	0.0431 (4)
C9	0.60420 (16)	1.04380 (6)	0.14722 (12)	0.0336 (3)
C10	0.43367 (18)	1.03906 (7)	0.16792 (13)	0.0415 (3)
H10	0.3947	1.0014	0.1994	0.050*
C11	0.32021 (19)	1.08937 (8)	0.14269 (15)	0.0478 (4)
H11	0.2061	1.0851	0.1560	0.057*
C12	0.37750 (19)	1.14550 (7)	0.09793 (14)	0.0467 (4)
H12	0.3019	1.1794	0.0818	0.056*
C13	0.54701 (18)	1.15209 (7)	0.07648 (13)	0.0422 (3)
H13	0.5850	1.1903	0.0462	0.051*
C14	0.65935 (17)	1.10152 (6)	0.10043 (12)	0.0352 (3)
C15	0.63790 (17)	0.81319 (6)	0.20774 (13)	0.0372 (3)
C16	0.69939 (18)	0.75399 (6)	0.17200 (13)	0.0402 (3)
C17	0.5962 (2)	0.69992 (7)	0.16825 (15)	0.0500 (4)
H17	0.6372	0.6609	0.1436	0.060*
C18	0.4323 (2)	0.70404 (8)	0.20125 (16)	0.0547 (4)
H18	0.3631	0.6677	0.1982	0.066*
C19	0.3707 (2)	0.76145 (8)	0.23863 (15)	0.0515 (4)
H19	0.2610	0.7639	0.2618	0.062*
C20	0.47349 (18)	0.81559 (7)	0.24150 (14)	0.0440 (4)
H20	0.4314	0.8543	0.2666	0.053*
C21	0.8836 (2)	1.15648 (10)	0.01693 (18)	0.0661 (5)
H21A	0.8196	1.1579	−0.0587	0.099*
H21B	1.0030	1.1519	0.0079	0.099*
H21C	0.8656	1.1955	0.0583	0.099*
C22	0.9277 (2)	0.69656 (8)	0.09613 (18)	0.0615 (5)
H22A	0.9330	0.6641	0.1556	0.092*
H22B	1.0402	0.7041	0.0736	0.092*
H22C	0.8538	0.6825	0.0293	0.092*
N1	0.63559 (14)	0.92907 (5)	0.18328 (11)	0.0358 (3)
O1	1.12212 (14)	0.94572 (6)	0.29471 (13)	0.0676 (4)
O2	0.82804 (12)	1.10343 (5)	0.08112 (10)	0.0470 (3)
O3	0.86248 (14)	0.75428 (5)	0.14027 (11)	0.0532 (3)
H1A	0.567 (2)	0.9222 (7)	0.1162 (15)	0.046 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0332 (6)	0.0317 (6)	0.0388 (8)	−0.0012 (5)	0.0068 (6)	−0.0005 (5)
C2	0.0361 (7)	0.0370 (7)	0.0508 (9)	−0.0062 (6)	−0.0013 (6)	−0.0005 (6)
C3	0.0589 (10)	0.0535 (9)	0.0449 (10)	0.0039 (8)	−0.0036 (7)	−0.0115 (7)
C4	0.0631 (11)	0.0733 (12)	0.0390 (9)	−0.0011 (9)	0.0097 (8)	−0.0040 (8)
C5	0.0598 (10)	0.0600 (10)	0.0444 (10)	−0.0077 (8)	−0.0023 (8)	0.0127 (8)
C6	0.0362 (7)	0.0377 (7)	0.0556 (10)	0.0035 (6)	−0.0008 (7)	0.0060 (7)
C7	0.0354 (7)	0.0309 (6)	0.0446 (8)	−0.0010 (5)	0.0093 (6)	0.0003 (6)
C8	0.0344 (7)	0.0488 (8)	0.0448 (9)	−0.0028 (6)	−0.0019 (6)	0.0000 (7)
C9	0.0345 (7)	0.0327 (6)	0.0336 (8)	−0.0008 (5)	0.0029 (5)	−0.0025 (5)
C10	0.0378 (7)	0.0399 (7)	0.0477 (9)	−0.0026 (6)	0.0091 (6)	0.0008 (6)
C11	0.0347 (7)	0.0532 (9)	0.0567 (10)	0.0050 (7)	0.0110 (7)	−0.0022 (8)
C12	0.0453 (8)	0.0438 (8)	0.0507 (10)	0.0126 (7)	0.0038 (7)	−0.0008 (7)
C13	0.0473 (8)	0.0356 (7)	0.0433 (9)	0.0015 (6)	0.0033 (7)	0.0029 (6)
C14	0.0339 (7)	0.0374 (7)	0.0346 (7)	−0.0021 (6)	0.0041 (5)	−0.0008 (6)
C15	0.0397 (7)	0.0348 (7)	0.0371 (8)	−0.0029 (6)	0.0031 (6)	0.0040 (6)
C16	0.0436 (8)	0.0344 (7)	0.0431 (9)	−0.0013 (6)	0.0060 (6)	0.0058 (6)
C17	0.0620 (10)	0.0343 (7)	0.0540 (10)	−0.0063 (7)	0.0073 (8)	0.0020 (7)
C18	0.0591 (10)	0.0470 (9)	0.0577 (11)	−0.0202 (8)	0.0045 (8)	0.0071 (8)
C19	0.0427 (8)	0.0565 (10)	0.0561 (10)	−0.0111 (7)	0.0089 (7)	0.0090 (8)
C20	0.0431 (8)	0.0427 (8)	0.0469 (9)	−0.0021 (6)	0.0086 (7)	0.0025 (7)
C21	0.0463 (9)	0.0827 (13)	0.0698 (13)	−0.0097 (9)	0.0081 (8)	0.0362 (10)
C22	0.0672 (11)	0.0458 (9)	0.0744 (13)	0.0096 (8)	0.0209 (9)	−0.0044 (8)
N1	0.0344 (6)	0.0299 (6)	0.0419 (7)	−0.0020 (5)	−0.0015 (5)	−0.0003 (5)
O1	0.0330 (6)	0.0683 (8)	0.1010 (11)	−0.0040 (5)	0.0034 (6)	0.0059 (7)
O2	0.0359 (5)	0.0468 (6)	0.0593 (7)	−0.0022 (4)	0.0104 (5)	0.0138 (5)
O3	0.0511 (6)	0.0345 (5)	0.0773 (8)	0.0022 (5)	0.0220 (6)	−0.0021 (5)

Geometric parameters (Å, º) top

C1—N1	1.4640 (16)	C11—C12	1.373 (2)
C1—C9	1.5110 (17)	C11—H11	0.9300
C1—C2	1.556 (2)	C12—C13	1.387 (2)
C1—H1	0.9800	C12—H12	0.9300
C2—C8	1.504 (2)	C13—C14	1.3846 (19)
C2—C3	1.537 (2)	C13—H13	0.9300
C2—H2	0.9800	C14—O2	1.3674 (16)
C3—C4	1.520 (2)	C15—C20	1.3879 (19)
C3—H3A	0.9700	C15—C16	1.4021 (19)
C3—H3B	0.9700	C16—O3	1.3684 (17)
C4—C5	1.522 (2)	C16—C17	1.3868 (19)
C4—H4A	0.9700	C17—C18	1.383 (2)
C4—H4B	0.9700	C17—H17	0.9300
C5—C6	1.534 (2)	C18—C19	1.376 (2)
C5—H5A	0.9700	C18—H18	0.9300
C5—H5B	0.9700	C19—C20	1.386 (2)
C6—C8	1.504 (2)	C19—H19	0.9300
C6—C7	1.552 (2)	C20—H20	0.9300
C6—H6	0.9800	C21—O2	1.4227 (18)
C7—N1	1.4636 (16)	C21—H21A	0.9600
C7—C15	1.5136 (17)	C21—H21B	0.9600
C7—H7	0.9800	C21—H21C	0.9600
C8—O1	1.2109 (17)	C22—O3	1.4216 (18)
C9—C10	1.3889 (18)	C22—H22A	0.9600
C9—C14	1.4044 (18)	C22—H22B	0.9600
C10—C11	1.388 (2)	C22—H22C	0.9600
C10—H10	0.9300	N1—H1A	0.907 (17)

N1—C1—C9	109.89 (10)	C11—C10—H10	119.3
N1—C1—C2	109.30 (11)	C9—C10—H10	119.3
C9—C1—C2	112.12 (11)	C12—C11—C10	119.60 (13)
N1—C1—H1	108.5	C12—C11—H11	120.2
C9—C1—H1	108.5	C10—C11—H11	120.2
C2—C1—H1	108.5	C11—C12—C13	120.61 (13)
C8—C2—C3	109.05 (13)	C11—C12—H12	119.7
C8—C2—C1	106.62 (11)	C13—C12—H12	119.7
C3—C2—C1	114.94 (12)	C14—C13—C12	119.63 (13)
C8—C2—H2	108.7	C14—C13—H13	120.2
C3—C2—H2	108.7	C12—C13—H13	120.2
C1—C2—H2	108.7	O2—C14—C13	123.71 (12)
C4—C3—C2	114.56 (13)	O2—C14—C9	115.45 (12)
C4—C3—H3A	108.6	C13—C14—C9	120.84 (12)
C2—C3—H3A	108.6	C20—C15—C16	118.20 (13)
C4—C3—H3B	108.6	C20—C15—C7	121.64 (12)
C2—C3—H3B	108.6	C16—C15—C7	120.09 (12)
H3A—C3—H3B	107.6	O3—C16—C17	123.81 (13)
C3—C4—C5	112.60 (14)	O3—C16—C15	115.77 (12)
C3—C4—H4A	109.1	C17—C16—C15	120.41 (13)
C5—C4—H4A	109.1	C18—C17—C16	119.98 (15)
C3—C4—H4B	109.1	C18—C17—H17	120.0
C5—C4—H4B	109.1	C16—C17—H17	120.0
H4A—C4—H4B	107.8	C19—C18—C17	120.47 (14)
C4—C5—C6	114.58 (13)	C19—C18—H18	119.8
C4—C5—H5A	108.6	C17—C18—H18	119.8
C6—C5—H5A	108.6	C18—C19—C20	119.51 (14)
C4—C5—H5B	108.6	C18—C19—H19	120.2
C6—C5—H5B	108.6	C20—C19—H19	120.2
H5A—C5—H5B	107.6	C19—C20—C15	121.41 (14)
C8—C6—C5	107.83 (13)	C19—C20—H20	119.3
C8—C6—C7	106.67 (12)	C15—C20—H20	119.3
C5—C6—C7	115.74 (12)	O2—C21—H21A	109.5
C8—C6—H6	108.8	O2—C21—H21B	109.5
C5—C6—H6	108.8	H21A—C21—H21B	109.5
C7—C6—H6	108.8	O2—C21—H21C	109.5
N1—C7—C15	109.52 (11)	H21A—C21—H21C	109.5
N1—C7—C6	110.07 (11)	H21B—C21—H21C	109.5
C15—C7—C6	112.93 (11)	O3—C22—H22A	109.5
N1—C7—H7	108.1	O3—C22—H22B	109.5
C15—C7—H7	108.1	H22A—C22—H22B	109.5
C6—C7—H7	108.1	O3—C22—H22C	109.5
O1—C8—C6	124.11 (14)	H22A—C22—H22C	109.5
O1—C8—C2	124.27 (14)	H22B—C22—H22C	109.5
C6—C8—C2	111.62 (12)	C7—N1—C1	113.70 (10)
C10—C9—C14	117.90 (12)	C7—N1—H1A	107.5 (10)
C10—C9—C1	122.25 (12)	C1—N1—H1A	108.7 (10)
C14—C9—C1	119.85 (11)	C14—O2—C21	117.45 (12)
C11—C10—C9	121.42 (13)	C16—O3—C22	118.24 (12)

N1—C1—C2—C8	58.24 (14)	C11—C12—C13—C14	0.0 (2)
C9—C1—C2—C8	−179.66 (11)	C12—C13—C14—O2	179.37 (14)
N1—C1—C2—C3	−62.72 (15)	C12—C13—C14—C9	−0.6 (2)
C9—C1—C2—C3	59.38 (15)	C10—C9—C14—O2	−179.60 (12)
C8—C2—C3—C4	−51.29 (18)	C1—C9—C14—O2	−0.42 (19)
C1—C2—C3—C4	68.33 (18)	C10—C9—C14—C13	0.4 (2)
C2—C3—C4—C5	43.6 (2)	C1—C9—C14—C13	179.54 (13)
C3—C4—C5—C6	−45.3 (2)	N1—C7—C15—C20	−26.68 (19)
C4—C5—C6—C8	54.13 (17)	C6—C7—C15—C20	96.37 (16)
C4—C5—C6—C7	−65.18 (18)	N1—C7—C15—C16	150.24 (13)
C8—C6—C7—N1	−57.03 (14)	C6—C7—C15—C16	−86.71 (16)
C5—C6—C7—N1	62.93 (15)	C20—C15—C16—O3	−179.66 (13)
C8—C6—C7—C15	−179.76 (11)	C7—C15—C16—O3	3.3 (2)
C5—C6—C7—C15	−59.81 (16)	C20—C15—C16—C17	1.4 (2)
C5—C6—C8—O1	117.71 (18)	C7—C15—C16—C17	−175.58 (13)
C7—C6—C8—O1	−117.36 (17)	O3—C16—C17—C18	−179.58 (15)
C5—C6—C8—C2	−62.84 (16)	C15—C16—C17—C18	−0.8 (2)
C7—C6—C8—C2	62.09 (16)	C16—C17—C18—C19	−0.4 (3)
C3—C2—C8—O1	−118.78 (18)	C17—C18—C19—C20	0.9 (3)
C1—C2—C8—O1	116.57 (17)	C18—C19—C20—C15	−0.2 (2)
C3—C2—C8—C6	61.77 (16)	C16—C15—C20—C19	−1.0 (2)
C1—C2—C8—C6	−62.88 (16)	C7—C15—C20—C19	176.01 (14)
N1—C1—C9—C10	17.27 (18)	C15—C7—N1—C1	−177.14 (11)
C2—C1—C9—C10	−104.49 (15)	C6—C7—N1—C1	58.14 (15)
N1—C1—C9—C14	−161.87 (12)	C9—C1—N1—C7	178.03 (11)
C2—C1—C9—C14	76.37 (16)	C2—C1—N1—C7	−58.54 (15)
C14—C9—C10—C11	0.4 (2)	C13—C14—O2—C21	−9.8 (2)
C1—C9—C10—C11	−178.73 (14)	C9—C14—O2—C21	170.19 (14)
C9—C10—C11—C12	−1.0 (2)	C17—C16—O3—C22	2.8 (2)
C10—C11—C12—C13	0.7 (2)	C15—C16—O3—C22	−176.03 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cg1ⁱ	0.90 (4)	2.75 (4)	3.58 (5)	152.87 (3)

Symmetry code: (i) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₅NO₃
M_r	351.43
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.8616 (2), 20.8443 (6), 11.4984 (3)
β (°)	95.867 (1)
V (Å³)	1874.37 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.58 × 0.42 × 0.35

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.945, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	14712, 4527, 3202
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.135, 1.03
No. of reflections	4527
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, −0.25

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cg1ⁱ	0.90 (4)	2.75 (4)	3.58 (5)	152.87 (3)

Symmetry code: (i) −x+1, −y+2, −z.

Acknowledgements

The authors acknowledge the Department of Chemistry, IIT Madras, for the X-ray data collection.

References

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