1-Methyl-2,4-bis­(2-methoxy­phen­yl)-3-aza­bicyclo­[3.3.1]nonan-9-one

Parthiban, P.; Ramkumar, V.; Jeong, Y.T.

doi:10.1107/S1600536809047928

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3103

doi:10.1107/S1600536809047928

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1-Methyl-2,4-bis(2-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one

P. Parthiban,^a V. Ramkumar ^b 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, TamilNadu, India
^*Correspondence e-mail: ytjeong@pknu.ac.kr

(Received 16 September 2009; accepted 12 November 2009; online 18 November 2009)

The crystal structure of the title compound, C₂₃H₂₇NO₃, shows that the compound exists in a chair–chair conformation with an equatorial disposition of 2-methoxyphenyl groups at an angle of 39.94 (3)° with respect to each other. An intermolecular N—H⋯π interaction is observed in the crystal packing.

Related literature

For the biological activity of 3-azabicyclononanes, see: Barker et al. (2005 ); Hardick et al. (1996 ); Jeyaraman & Avila (1981 ). For related structures with similar conformations, see: Parthiban et al. (2008 ); Parthiban, Ramkumar & Jeong (2009 ); Parthiban, Ramkumar, Kim et al. (2009 ). For a related structure with a chair–boat conformation, see: Smith-Verdier et al. (1983 ). For a related structure with a boat–boat conformation, see: Padegimas & Kovacic (1972 ). For ring puckering parameters, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₂₃H₂₇NO₃
M_r = 365.46
Monoclinic, P 2₁ /n
a = 7.9569 (3) Å
b = 20.8291 (9) Å
c = 11.6708 (6) Å
β = 96.297 (2)°
V = 1922.59 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.41 × 0.24 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.288, T_max = 0.980
14049 measured reflections
4608 independent reflections
3166 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.127
S = 1.02
4608 reflections
251 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cg1ⁱ	0.862 (15)	2.852 (3)	3.6276 (14)	150.6 (12)
Symmetry code: (i) -x+1, -y, -z+1. Cg1 is the centroid of the C16–C21 ring.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (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 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809047928/ez2190sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809047928/ez2190Isup2.hkl

checkCIF report

Comment top

3-Azabicyclononanes are an important class of heterocycles due to their broad spectrum biological activities (Jeyaraman & Avila, 1981; Hardick et al., 1996; Barker et al., 2005). Owing to the diverse possibilities in conformations, viz., chair-chair (Parthiban et al., 2008; Parthiban, Ramkumar & Jeong, 2009; Parthiban, Ramkumar, Kim et al., 2009), chair-boat (Smith-Verdier et al., 1983) and boat-boat (Padegimas & Kovacic, 1972) for the azabicycle, the present crystal study was undertaken to explore the conformation, stereochemistry and bonding of the title compound.

The analysis of torsion angles, asymmetry parameters and least-squares planes calculated for the title compound shows that the piperidine ring adopts a near ideal chair conformation with deviations of the ring atoms C8 and N1 from the C1/C2/C6/C7 plane by 0.655 (3) Å and -0.708 (3) Å, respectively. The smallest displacement asymmetry parameters are q2 = 0.0341 (15) Å and q3 =0.6123 (15) Å (Nardelli, 1983). The total puckering amplitude, Q_T = 0.6132 (15) Å and θ = 3.14 (14) ° (Cremer & Pople, 1975). The cyclohexane ring deviates from the ideal chair conformation by the deviation of ring atoms C4 and C8 from the C2/C3/C5/C6 plane by -0.697 (4) Å and 0.535 (3) Å, respectively. The smallest displacement asymmetry parameters are q2 = 0.1216 (17) Å and q3 = 0.5322 (17) Å (Nardelli, 1983); total puckering amplitude, Q_T = 0.5460 (16) Å, and θ =12.87 (18)° (Cremer & Pople, 1975). Hence, the title compound C₂₃H₂₇NO₃, exists in a chair-chair conformation with an equatorial orientation of the ortho-methoxyphenyl groups on the heterocycle, which are orientated at an angle of 39.94 (3)° with respect to each other. The crystal structure is stabilized by an intermolecular N-H···π interaction between N1-H1A and the C16/C17/C18/C19/C20/C21 ring in a neighbouring molecule [N···centroid distance of 2.852 (3)Å; symmetry operator: 1-x,-y,1-z].

Related literature top

For the biological activity of 3-azabicyclononanes, see: Barker et al. (2005); Hardick et al. (1996); Jeyaraman & Avila (1981). For related structures with similar conformations, see: Parthiban et al. (2008); Parthiban, Ramkumar & Jeong (2009); Parthiban, Ramkumar, Kim et al. (2009). For a related structure with a chair–boat conformation, see: Smith-Verdier et al. (1983). For a related structure with a boat–boat conformation, see: Padegimas & Kovacic (1972). For ring puckering parameters, see: Cremer & Pople (1975); Nardelli (1983). Cg1 is the centroid of the C16–C21 ring.

Experimental top

A mixture of 2-methylcyclohexanone (0.05 mol, 5.61 g) and ortho-methoxybenzaldehyde (0.1 mol, 13.62 g) was added to a warm solution of ammonium acetate (0.075 mol, 5.78 g) in 50 ml of absolute ethanol. The mixture was gently warmed with stirring until a yellow color was obtained during the mixing of the reactants and then allowed to stir at 303–308° K until formation of the product. At the end, the crude azabicyclic ketone was separated by filtration and washed with a 1:5 ethanol-ether mixture until the solid became colorless. Recrystallization of the compound from ethanol gave X-ray diffraction quality crystals of 1-methyl-2,4-bis(2-methoxyphenyl)-3- azabicyclo[3.3.1]nonan-9-one.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (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) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. ORTEP diagram of the molecule, showing the atom numbering scheme, with atoms represented as 30% probability ellipsoids.

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

Crystal data top

C₂₃H₂₇NO₃	F(000) = 784
M_r = 365.46	D_x = 1.263 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4178 reflections
a = 7.9569 (3) Å	θ = 2.6–28.0°
b = 20.8291 (9) Å	µ = 0.08 mm⁻¹
c = 11.6708 (6) Å	T = 298 K
β = 96.297 (2)°	Block, colourless
V = 1922.59 (15) Å³	0.41 × 0.24 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	4608 independent reflections
Radiation source: fine-focus sealed tube	3166 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −8→10
T_min = 0.288, T_max = 0.980	k = −27→27
14049 measured reflections	l = −15→15

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) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0542P)² + 0.4061P] where P = (F_o² + 2F_c²)/3
4608 reflections	(Δ/σ)_max < 0.001
251 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₃H₂₇NO₃	V = 1922.59 (15) Å³
M_r = 365.46	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.9569 (3) Å	µ = 0.08 mm⁻¹
b = 20.8291 (9) Å	T = 298 K
c = 11.6708 (6) Å	0.41 × 0.24 × 0.20 mm
β = 96.297 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4608 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	3166 reflections with I > 2σ(I)
T_min = 0.288, T_max = 0.980	R_int = 0.026
14049 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.22 e Å⁻³
4608 reflections	Δρ_min = −0.21 e Å⁻³
251 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	0.23693 (17)	0.12454 (6)	0.28186 (12)	0.0323 (3)
H1	0.1669	0.1269	0.3458	0.039*
C2	0.11755 (18)	0.10977 (7)	0.16904 (12)	0.0363 (3)
C3	0.2099 (2)	0.10169 (8)	0.06003 (13)	0.0431 (4)
H3A	0.1254	0.0972	−0.0060	0.052*
H3B	0.2725	0.1408	0.0492	0.052*
C4	0.3315 (2)	0.04531 (8)	0.06032 (14)	0.0473 (4)
H4A	0.4347	0.0557	0.1089	0.057*
H4B	0.3604	0.0385	−0.0174	0.057*
C5	0.2575 (2)	−0.01655 (8)	0.10382 (14)	0.0465 (4)
H5A	0.3483	−0.0473	0.1211	0.056*
H5B	0.1790	−0.0345	0.0427	0.056*
C6	0.16498 (18)	−0.00768 (7)	0.21184 (13)	0.0372 (3)
H6	0.1050	−0.0475	0.2256	0.045*
C7	0.27979 (17)	0.01007 (6)	0.32297 (12)	0.0321 (3)
H7	0.2089	0.0140	0.3862	0.039*
C8	0.03777 (19)	0.04528 (7)	0.19078 (12)	0.0383 (3)
C9	0.33357 (18)	0.18729 (6)	0.27865 (12)	0.0334 (3)
C10	0.49093 (19)	0.18943 (7)	0.23764 (14)	0.0407 (4)
H10	0.5344	0.1522	0.2082	0.049*
C11	0.5850 (2)	0.24549 (8)	0.23944 (15)	0.0479 (4)
H11	0.6903	0.2457	0.2119	0.058*
C12	0.5214 (2)	0.30076 (8)	0.28224 (16)	0.0505 (4)
H12	0.5839	0.3385	0.2836	0.061*
C13	0.3655 (2)	0.30062 (7)	0.32316 (14)	0.0452 (4)
H13	0.3230	0.3383	0.3516	0.054*
C14	0.27187 (19)	0.24449 (7)	0.32211 (12)	0.0370 (3)
C15	−0.0179 (2)	0.16144 (8)	0.14796 (16)	0.0530 (4)
H15A	−0.0981	0.1490	0.0843	0.079*
H15B	0.0340	0.2014	0.1305	0.079*
H15C	−0.0748	0.1665	0.2158	0.079*
C16	0.41183 (18)	−0.04090 (6)	0.35486 (12)	0.0325 (3)
C17	0.36550 (18)	−0.09743 (7)	0.40848 (12)	0.0355 (3)
C18	0.4828 (2)	−0.14549 (7)	0.43706 (13)	0.0432 (4)
H18	0.4506	−0.1831	0.4717	0.052*
C19	0.6482 (2)	−0.13728 (8)	0.41378 (14)	0.0487 (4)
H19	0.7271	−0.1695	0.4330	0.058*
C20	0.6970 (2)	−0.08216 (8)	0.36268 (15)	0.0497 (4)
H20	0.8087	−0.0767	0.3481	0.060*
C21	0.57849 (19)	−0.03438 (7)	0.33286 (14)	0.0421 (4)
H21	0.6118	0.0028	0.2974	0.050*
C22	0.0402 (2)	0.29848 (8)	0.39536 (17)	0.0566 (5)
H22A	0.1056	0.3174	0.4608	0.085*
H22B	−0.0717	0.2894	0.4143	0.085*
H22C	0.0339	0.3278	0.3316	0.085*
C23	0.1527 (3)	−0.15186 (11)	0.49954 (19)	0.0793 (7)
H23A	0.1658	−0.1920	0.4610	0.119*
H23B	0.0368	−0.1466	0.5134	0.119*
H23C	0.2235	−0.1515	0.5717	0.119*
N1	0.35903 (15)	0.07229 (5)	0.30669 (11)	0.0324 (3)
O1	−0.11245 (14)	0.03744 (6)	0.19326 (12)	0.0606 (4)
O2	0.11835 (14)	0.24067 (5)	0.36491 (10)	0.0498 (3)
O3	0.19994 (13)	−0.10095 (5)	0.42960 (10)	0.0484 (3)
H1A	0.4203 (18)	0.0824 (7)	0.3696 (13)	0.032 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0345 (7)	0.0274 (7)	0.0357 (7)	0.0025 (5)	0.0074 (6)	0.0021 (6)
C2	0.0341 (8)	0.0356 (8)	0.0387 (8)	0.0037 (6)	0.0025 (6)	0.0037 (6)
C3	0.0492 (9)	0.0446 (9)	0.0360 (8)	−0.0024 (7)	0.0065 (7)	0.0062 (7)
C4	0.0524 (10)	0.0531 (10)	0.0386 (8)	0.0012 (8)	0.0149 (7)	−0.0044 (7)
C5	0.0556 (10)	0.0417 (9)	0.0415 (9)	0.0027 (7)	0.0019 (7)	−0.0094 (7)
C6	0.0371 (8)	0.0303 (7)	0.0437 (8)	−0.0074 (6)	0.0027 (6)	−0.0005 (6)
C7	0.0336 (7)	0.0281 (7)	0.0356 (7)	−0.0004 (6)	0.0079 (6)	0.0008 (6)
C8	0.0346 (8)	0.0454 (9)	0.0344 (7)	−0.0040 (7)	0.0021 (6)	0.0012 (6)
C9	0.0375 (8)	0.0278 (7)	0.0352 (7)	0.0011 (6)	0.0047 (6)	0.0033 (6)
C10	0.0406 (8)	0.0338 (8)	0.0490 (9)	0.0025 (6)	0.0104 (7)	0.0025 (7)
C11	0.0397 (9)	0.0431 (9)	0.0625 (11)	−0.0038 (7)	0.0124 (8)	0.0071 (8)
C12	0.0538 (10)	0.0348 (9)	0.0637 (11)	−0.0107 (7)	0.0096 (8)	0.0045 (8)
C13	0.0571 (10)	0.0285 (8)	0.0511 (9)	0.0001 (7)	0.0099 (8)	−0.0009 (7)
C14	0.0426 (8)	0.0314 (7)	0.0379 (8)	0.0021 (6)	0.0085 (6)	0.0037 (6)
C15	0.0466 (10)	0.0492 (10)	0.0613 (11)	0.0119 (8)	−0.0018 (8)	0.0049 (8)
C16	0.0365 (8)	0.0272 (7)	0.0340 (7)	0.0002 (6)	0.0053 (6)	−0.0024 (6)
C17	0.0404 (8)	0.0320 (7)	0.0337 (7)	−0.0031 (6)	0.0025 (6)	−0.0014 (6)
C18	0.0578 (10)	0.0298 (7)	0.0408 (8)	0.0021 (7)	0.0006 (7)	0.0024 (6)
C19	0.0536 (10)	0.0414 (9)	0.0498 (9)	0.0186 (8)	−0.0003 (8)	−0.0031 (7)
C20	0.0395 (9)	0.0502 (10)	0.0608 (10)	0.0094 (7)	0.0116 (8)	−0.0031 (8)
C21	0.0401 (8)	0.0365 (8)	0.0510 (9)	0.0002 (7)	0.0117 (7)	0.0023 (7)
C22	0.0599 (11)	0.0430 (10)	0.0702 (12)	0.0106 (8)	0.0220 (9)	−0.0069 (8)
C23	0.0611 (13)	0.0974 (16)	0.0793 (14)	−0.0177 (11)	0.0073 (11)	0.0504 (13)
N1	0.0324 (6)	0.0256 (6)	0.0383 (7)	−0.0002 (5)	−0.0004 (5)	−0.0006 (5)
O1	0.0336 (6)	0.0681 (8)	0.0795 (9)	−0.0079 (6)	0.0039 (6)	0.0119 (7)
O2	0.0552 (7)	0.0316 (6)	0.0678 (8)	0.0036 (5)	0.0292 (6)	−0.0024 (5)
O3	0.0429 (6)	0.0469 (7)	0.0564 (7)	−0.0067 (5)	0.0093 (5)	0.0167 (5)

Geometric parameters (Å, º) top

C1—N1	1.4663 (17)	C12—C13	1.377 (2)
C1—C9	1.5191 (19)	C12—H12	0.9300
C1—C2	1.5672 (19)	C13—C14	1.386 (2)
C1—H1	0.9800	C13—H13	0.9300
C2—C8	1.519 (2)	C14—O2	1.3719 (17)
C2—C15	1.524 (2)	C15—H15A	0.9600
C2—C3	1.547 (2)	C15—H15B	0.9600
C3—C4	1.521 (2)	C15—H15C	0.9600
C3—H3A	0.9700	C16—C21	1.385 (2)
C3—H3B	0.9700	C16—C17	1.4016 (19)
C4—C5	1.526 (2)	C17—O3	1.3685 (17)
C4—H4A	0.9700	C17—C18	1.384 (2)
C4—H4B	0.9700	C18—C19	1.384 (2)
C5—C6	1.539 (2)	C18—H18	0.9300
C5—H5A	0.9700	C19—C20	1.369 (2)
C5—H5B	0.9700	C19—H19	0.9300
C6—C8	1.499 (2)	C20—C21	1.389 (2)
C6—C7	1.547 (2)	C20—H20	0.9300
C6—H6	0.9800	C21—H21	0.9300
C7—N1	1.4628 (17)	C22—O2	1.4181 (18)
C7—C16	1.5111 (19)	C22—H22A	0.9600
C7—H7	0.9800	C22—H22B	0.9600
C8—O1	1.2099 (18)	C22—H22C	0.9600
C9—C10	1.389 (2)	C23—O3	1.414 (2)
C9—C14	1.4044 (19)	C23—H23A	0.9600
C10—C11	1.386 (2)	C23—H23B	0.9600
C10—H10	0.9300	C23—H23C	0.9600
C11—C12	1.373 (2)	N1—H1A	0.862 (15)
C11—H11	0.9300

N1—C1—C9	108.50 (11)	C12—C11—H11	120.3
N1—C1—C2	110.35 (11)	C10—C11—H11	120.3
C9—C1—C2	114.20 (11)	C11—C12—C13	120.41 (15)
N1—C1—H1	107.9	C11—C12—H12	119.8
C9—C1—H1	107.9	C13—C12—H12	119.8
C2—C1—H1	107.9	C12—C13—C14	120.17 (15)
C8—C2—C15	110.51 (13)	C12—C13—H13	119.9
C8—C2—C3	106.63 (12)	C14—C13—H13	119.9
C15—C2—C3	109.61 (13)	O2—C14—C13	123.04 (13)
C8—C2—C1	105.02 (11)	O2—C14—C9	116.28 (12)
C15—C2—C1	110.47 (12)	C13—C14—C9	120.67 (14)
C3—C2—C1	114.42 (12)	C2—C15—H15A	109.5
C4—C3—C2	116.20 (12)	C2—C15—H15B	109.5
C4—C3—H3A	108.2	H15A—C15—H15B	109.5
C2—C3—H3A	108.2	C2—C15—H15C	109.5
C4—C3—H3B	108.2	H15A—C15—H15C	109.5
C2—C3—H3B	108.2	H15B—C15—H15C	109.5
H3A—C3—H3B	107.4	C21—C16—C17	117.99 (13)
C3—C4—C5	112.60 (14)	C21—C16—C7	122.65 (12)
C3—C4—H4A	109.1	C17—C16—C7	119.37 (13)
C5—C4—H4A	109.1	O3—C17—C18	123.70 (13)
C3—C4—H4B	109.1	O3—C17—C16	115.52 (12)
C5—C4—H4B	109.1	C18—C17—C16	120.78 (14)
H4A—C4—H4B	107.8	C19—C18—C17	119.62 (14)
C4—C5—C6	114.05 (12)	C19—C18—H18	120.2
C4—C5—H5A	108.7	C17—C18—H18	120.2
C6—C5—H5A	108.7	C20—C19—C18	120.67 (14)
C4—C5—H5B	108.7	C20—C19—H19	119.7
C6—C5—H5B	108.7	C18—C19—H19	119.7
H5A—C5—H5B	107.6	C19—C20—C21	119.53 (16)
C8—C6—C5	109.21 (12)	C19—C20—H20	120.2
C8—C6—C7	106.72 (11)	C21—C20—H20	120.2
C5—C6—C7	115.07 (12)	C16—C21—C20	121.40 (14)
C8—C6—H6	108.6	C16—C21—H21	119.3
C5—C6—H6	108.6	C20—C21—H21	119.3
C7—C6—H6	108.6	O2—C22—H22A	109.5
N1—C7—C16	110.89 (11)	O2—C22—H22B	109.5
N1—C7—C6	109.03 (11)	H22A—C22—H22B	109.5
C16—C7—C6	111.68 (11)	O2—C22—H22C	109.5
N1—C7—H7	108.4	H22A—C22—H22C	109.5
C16—C7—H7	108.4	H22B—C22—H22C	109.5
C6—C7—H7	108.4	O3—C23—H23A	109.5
O1—C8—C6	123.22 (14)	O3—C23—H23B	109.5
O1—C8—C2	123.74 (14)	H23A—C23—H23B	109.5
C6—C8—C2	113.02 (12)	O3—C23—H23C	109.5
C10—C9—C14	117.47 (13)	H23A—C23—H23C	109.5
C10—C9—C1	120.91 (12)	H23B—C23—H23C	109.5
C14—C9—C1	121.54 (13)	C7—N1—C1	113.43 (11)
C11—C10—C9	121.82 (14)	C7—N1—H1A	108.5 (10)
C11—C10—H10	119.1	C1—N1—H1A	106.7 (10)
C9—C10—H10	119.1	C14—O2—C22	118.30 (12)
C12—C11—C10	119.47 (15)	C17—O3—C23	117.79 (13)

N1—C1—C2—C8	56.53 (14)	C9—C10—C11—C12	−0.4 (3)
C9—C1—C2—C8	179.06 (12)	C10—C11—C12—C13	0.0 (3)
N1—C1—C2—C15	175.70 (12)	C11—C12—C13—C14	0.4 (3)
C9—C1—C2—C15	−61.77 (16)	C12—C13—C14—O2	177.88 (14)
N1—C1—C2—C3	−60.04 (15)	C12—C13—C14—C9	−0.5 (2)
C9—C1—C2—C3	62.49 (16)	C10—C9—C14—O2	−178.29 (13)
C8—C2—C3—C4	−51.75 (17)	C1—C9—C14—O2	−1.4 (2)
C15—C2—C3—C4	−171.39 (14)	C10—C9—C14—C13	0.2 (2)
C1—C2—C3—C4	63.89 (17)	C1—C9—C14—C13	177.06 (13)
C2—C3—C4—C5	44.90 (19)	N1—C7—C16—C21	−20.15 (19)
C3—C4—C5—C6	−43.79 (19)	C6—C7—C16—C21	101.66 (15)
C4—C5—C6—C8	51.92 (17)	N1—C7—C16—C17	160.12 (12)
C4—C5—C6—C7	−68.05 (17)	C6—C7—C16—C17	−78.06 (16)
C8—C6—C7—N1	−58.41 (14)	C21—C16—C17—O3	179.13 (12)
C5—C6—C7—N1	62.92 (15)	C7—C16—C17—O3	−1.14 (19)
C8—C6—C7—C16	178.70 (11)	C21—C16—C17—C18	−0.8 (2)
C5—C6—C7—C16	−59.97 (16)	C7—C16—C17—C18	178.93 (13)
C5—C6—C8—O1	119.23 (16)	O3—C17—C18—C19	−179.09 (14)
C7—C6—C8—O1	−115.79 (16)	C16—C17—C18—C19	0.8 (2)
C5—C6—C8—C2	−62.18 (15)	C17—C18—C19—C20	−0.1 (2)
C7—C6—C8—C2	62.80 (15)	C18—C19—C20—C21	−0.7 (3)
C15—C2—C8—O1	−1.6 (2)	C17—C16—C21—C20	0.0 (2)
C3—C2—C8—O1	−120.63 (16)	C7—C16—C21—C20	−179.71 (14)
C1—C2—C8—O1	117.57 (16)	C19—C20—C21—C16	0.7 (3)
C15—C2—C8—C6	179.84 (13)	C16—C7—N1—C1	−176.79 (11)
C3—C2—C8—C6	60.79 (15)	C6—C7—N1—C1	59.86 (15)
C1—C2—C8—C6	−61.01 (15)	C9—C1—N1—C7	174.42 (11)
N1—C1—C9—C10	34.09 (17)	C2—C1—N1—C7	−59.77 (15)
C2—C1—C9—C10	−89.44 (16)	C13—C14—O2—C22	9.9 (2)
N1—C1—C9—C14	−142.65 (13)	C9—C14—O2—C22	−171.66 (14)
C2—C1—C9—C14	93.82 (16)	C18—C17—O3—C23	9.8 (2)
C14—C9—C10—C11	0.2 (2)	C16—C17—O3—C23	−170.10 (16)
C1—C9—C10—C11	−176.64 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cg1ⁱ	0.862 (15)	2.852 (3)	3.6276 (14)	150.6 (12)

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₇NO₃
M_r	365.46
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.9569 (3), 20.8291 (9), 11.6708 (6)
β (°)	96.297 (2)
V (Å³)	1922.59 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.41 × 0.24 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.288, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	14049, 4608, 3166
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.127, 1.02
No. of reflections	4608
No. of parameters	251
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.21

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cg1ⁱ	0.862 (15)	2.852 (3)	3.6276 (14)	150.6 (12)

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

This research was supported by the Industrial Technology Devlopment Program, which was conducted by the Ministry of Knowledge Economy of the Korean Government. The authors acknowledge the Department of Chemistry, IIT Madras, for the X-ray data collection.

References

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