2,4-Bis(2-eth­oxy­phen­yl)-7-methyl-3-aza­bicyclo­[3.3.1]nonan-9-one

Parthiban, P.; Ramkumar, V.; Park, D.H.; Jeong, Y.T.

doi:10.1107/S1600536811018472

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1475-o1476

doi:10.1107/S1600536811018472

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2,4-Bis(2-ethoxyphenyl)-7-methyl-3-azabicyclo[3.3.1]nonan-9-one

P. Parthiban,^a V. Ramkumar,^b Dong Ho Park ^c and Yeon Tae Jeong ^a ^*

^aDepartment of Image Science and Engineering, Pukyong National University, Busan 608 737, Republic of Korea, ^bDepartment of Chemistry, Indian Institute of Technology Madras, Chennai, Tamilnadu, India, and ^cDepartment of Biomedicinal Chemistry, Inje University, Gimhae, Gyeongnam 621 749, Republic of Korea
^*Correspondence e-mail: ytjeong@pknu.ac.kr

(Received 12 May 2011; accepted 16 May 2011; online 20 May 2011)

The crystal structure of the title compound, C₂₅H₃₁NO₃, exists in a twin-chair conformation with an equatorial orientation of the ortho-ethoxyphenyl groups. According to Cremer and Pople [Cremer & Pople (1975 ), J. Am. Chem. Soc. 97, 1354–1358], both the piperidone and cyclohexanone rings are significantly puckered with total puckering amplitutdes Q_T of 0.5889 (18) and 0.554 (2) Å, respectively. The ortho-ethoxyphenyl groups are located on either side of the secondary amino group and make a dihedral angle of 12.41 (4)° with respect to each other. The methyl group on the cyclohexanone part occupies an exocyclic equatorial disposition. The crystal packing is stabilized by weak van der Waals interactions.

Related literature

For the synthesis and biological activity of 3-azabicyclo[3.3.1]nonan-9-ones, see: Jeyaraman & Avila (1981 ); Barker et al. (2005 ); Parthiban et al. (2009a , 2010b ,c , 2011 ). For related structures, see: Parthiban et al. (2009b ,c , 2010a ,c); Cox et al. (1985 ); Smith-Verdier et al. (1983 ); Padegimas & Kovacic (1972 ). For ring puckering parameters, see: Cremer & Pople (1975); Nardelli (1983 ).

Experimental

Crystal data

C₂₅H₃₁NO₃
M_r = 393.51
Monoclinic, P 2₁ /n
a = 10.3147 (6) Å
b = 11.8817 (6) Å
c = 18.7809 (10) Å
β = 100.866 (2)°
V = 2260.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.35 × 0.28 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.974, T_max = 0.989
12446 measured reflections
3876 independent reflections
2415 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.117
S = 1.03
3876 reflections
269 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.13 e Å⁻³

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 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811018472/lw2064sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018472/lw2064Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811018472/lw2064Isup3.cml

checkCIF report

Comment top

The 3-azabicycle nucleus is an important class of pharmacophore due to its broad spectrum of biological activities such as antibacterial, antimycobacterial, antifungal, anticancer, antitussive, antiinflammatory, sedative, antipyretic and calcium antagonistic activity (Jeyaraman & Avila, 1981; Barker et al., 2005; Parthiban et al., 2009a, 2010b, 2010c, 2011). Its biological significane prompted the medicinal chemists to synthesize some structural analogs. Since the stereochemistry plays an important role in biological actions, it is of immense help to establish the stereochemistry of the synthesized bio-potent molecules. Since several stereomers are possible for the synthesized title compound along with different conformations such as chair-chair (Parthiban et al., 2009b, 2009c, 2010a; Cox et al., 1985), chair-boat (Parthiban et al., 2010c; Smith-Verdier et al., 1983) and boat-boat (Padegimas & Kovacic, 1972), the title compound was undertaken for the present single-crystal XRD study to establish the stereochemistry.

The analysis of torsion angles, asymmetry parameters and puckering parameters calculated for the title compound shows that the piperidine ring slightly deviates the ideal chair conformation. According to Cremer & Pople, the total puckering amplitude, Q_T is 0.5889 (18) Å and the phase angle θ is 7.19 (18)° (Cremer & Pople, 1975) for the piperidine ring. Also according to Nardelli, the smallest displacement asymmetry parameters q₂ and q₃ are 0.0741 (18) and 0.5843 (18)°, respectively (Nardelli, 1983).

The cyclohexanone ring deviates more than the piperidone ring from the ideal chair conformation. According to Cremer and Pople the Q_T = 0.554 (2) and θ = 12.2 (2)° (Cremer & Pople, 1975) and by Nardelli, q₂ = 0.118 (2) and q₃ = 0.541 (2)° (Nardelli, 1983).

The torsion angles of C8—C6—C7—C15 and C8—C2—C1—C9 are -179.07 (14) and 176.83 (14)°, respectively.

The above detailed analysis of the title compound C₂₅H₃₁NO₃, clearly shows that the compound exists in a twin-chair conformation with an equatorial orientation of the ortho-ethoxyphenyl units on both sides of the secondary amino group. The ortho-ethoxyphenyl groups are orientated at a dihedral angle of 12.41 (4)° with respect to each other. The methyl group attached to the cyclohexanone part occupies an exocyclic equatorial disposition. The crystal packing is stabilized by weak van der Waals interactions.

Related literature top

For the synthesis and biological activity of 3-azabicyclo[3.3.1]nonan-9-ones, see: Jeyaraman & Avila (1981); Barker et al. (2005); Parthiban et al. (2009a, 2010b,c, 2011). For related structures, see: Parthiban et al. (2009b,c, 2010a); Cox et al. (1985); Smith-Verdier et al. (1983); Padegimas & Kovacic (1972). For ring puckering parameters, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

The 7-methyl-2,4-bis(2-ethoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one was synthesized by a modified and an optimized Mannich condensation in one-pot, using 2-ethoxybenzaldehyde (0.1 mol, 15.02 g/13.94 ml), 4-methylcyclohexanone (0.05 mol, 5.61 g/6.14 ml) and ammonium acetate (0.075 mol, 5.78 g) in a 50 ml of absolute ethanol. The mixture was gently warmed on a hot plate at 303–308 K (30–35° C) with moderate stirring till the complete consumption of the starting materials, which was monitored by TLC. At the end, the crude azabicyclic ketone was separated by filtration and gently washed with 1:5 cold ethanol-ether mixture. X-ray diffraction quality crystals of the title compound were obtained by slow evaporation from ethanol.

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); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Anistropic displacement representation of the molecule with atoms represented with 30% probability ellipsoids.

2,4-Bis(2-ethoxyphenyl)-7-methyl-3-azabicyclo[3.3.1]nonan-9-one top

Crystal data top

C₂₅H₃₁NO₃	F(000) = 848
M_r = 393.51	D_x = 1.156 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3407 reflections
a = 10.3147 (6) Å	θ = 2.6–21.8°
b = 11.8817 (6) Å	µ = 0.08 mm⁻¹
c = 18.7809 (10) Å	T = 298 K
β = 100.866 (2)°	Block, colourless
V = 2260.4 (2) Å³	0.35 × 0.28 × 0.15 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	3876 independent reflections
Radiation source: fine-focus sealed tube	2415 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 25.6°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→11
T_min = 0.974, T_max = 0.989	k = −14→14
12446 measured reflections	l = −22→16

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.047P)² + 0.3732P] where P = (F_o² + 2F_c²)/3
3876 reflections	(Δ/σ)_max < 0.001
269 parameters	Δρ_max = 0.12 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₂₅H₃₁NO₃	V = 2260.4 (2) Å³
M_r = 393.51	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.3147 (6) Å	µ = 0.08 mm⁻¹
b = 11.8817 (6) Å	T = 298 K
c = 18.7809 (10) Å	0.35 × 0.28 × 0.15 mm
β = 100.866 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3876 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2415 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.989	R_int = 0.025
12446 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.12 e Å⁻³
3876 reflections	Δρ_min = −0.13 e Å⁻³
269 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	1.07118 (17)	0.68920 (14)	0.12439 (9)	0.0475 (4)
H1	1.1292	0.6243	0.1379	0.057*
C2	0.99532 (18)	0.71301 (15)	0.18699 (9)	0.0553 (5)
H2	1.0598	0.7203	0.2323	0.066*
C3	0.9088 (2)	0.81806 (16)	0.17738 (11)	0.0676 (6)
H3A	0.8763	0.8312	0.2219	0.081*
H3B	0.9629	0.8821	0.1698	0.081*
C4	0.7921 (2)	0.81182 (16)	0.11504 (11)	0.0659 (6)
H4	0.8258	0.8178	0.0698	0.079*
C5	0.72060 (18)	0.70069 (16)	0.11430 (10)	0.0585 (5)
H5A	0.6605	0.6933	0.0681	0.070*
H5B	0.6678	0.7023	0.1519	0.070*
C6	0.80887 (17)	0.59660 (14)	0.12573 (8)	0.0489 (4)
H6	0.7547	0.5311	0.1324	0.059*
C7	0.88565 (16)	0.57076 (14)	0.06386 (8)	0.0454 (4)
H7	0.9362	0.5012	0.0759	0.054*
C8	0.90968 (17)	0.61391 (15)	0.19325 (9)	0.0522 (5)
C9	1.15495 (18)	0.78883 (15)	0.11170 (10)	0.0522 (5)
C10	1.1188 (2)	0.86086 (16)	0.05364 (11)	0.0643 (5)
H10	1.0419	0.8464	0.0202	0.077*
C11	1.1939 (3)	0.95391 (18)	0.04389 (15)	0.0868 (7)
H11	1.1680	1.0011	0.0042	0.104*
C12	1.3066 (3)	0.9759 (2)	0.09300 (18)	0.0975 (8)
H12	1.3576	1.0384	0.0866	0.117*
C13	1.3453 (2)	0.9065 (2)	0.15186 (15)	0.0861 (7)
H13	1.4219	0.9224	0.1852	0.103*
C14	1.27035 (19)	0.81263 (17)	0.16149 (11)	0.0629 (5)
C15	0.79067 (17)	0.55378 (15)	−0.00749 (9)	0.0495 (5)
C16	0.71335 (18)	0.45680 (16)	−0.01864 (10)	0.0569 (5)
C17	0.6211 (2)	0.4422 (2)	−0.08214 (12)	0.0741 (6)
H17	0.5700	0.3773	−0.0892	0.089*
C18	0.6060 (2)	0.5244 (3)	−0.13440 (12)	0.0885 (8)
H18	0.5439	0.5150	−0.1768	0.106*
C19	0.6809 (2)	0.6193 (2)	−0.12479 (11)	0.0871 (7)
H19	0.6707	0.6743	−0.1607	0.105*
C20	0.7721 (2)	0.63362 (18)	−0.06142 (10)	0.0671 (6)
H20	0.8223	0.6991	−0.0551	0.080*
C21	0.6966 (3)	0.9105 (2)	0.11769 (15)	0.1095 (9)
H21A	0.6663	0.9092	0.1630	0.164*
H21B	0.6225	0.9037	0.0785	0.164*
H21C	0.7414	0.9803	0.1133	0.164*
C22	1.4219 (2)	0.7531 (3)	0.26893 (13)	0.1002 (9)
H22A	1.4220	0.8246	0.2938	0.120*
H22B	1.4965	0.7517	0.2442	0.120*
C23	1.4315 (3)	0.6584 (3)	0.32186 (15)	0.1209 (11)
H23A	1.3550	0.6583	0.3441	0.181*
H23B	1.5093	0.6676	0.3585	0.181*
H23C	1.4365	0.5883	0.2970	0.181*
C24	0.6380 (2)	0.29441 (18)	0.03834 (13)	0.0819 (7)
H24A	0.6386	0.2398	0.0000	0.098*
H24B	0.5510	0.3284	0.0315	0.098*
C25	0.6690 (3)	0.2388 (2)	0.10965 (16)	0.1147 (10)
H25A	0.7545	0.2041	0.1155	0.172*
H25B	0.6037	0.1823	0.1127	0.172*
H25C	0.6691	0.2936	0.1472	0.172*
H1N	1.0230 (17)	0.6437 (14)	0.0263 (9)	0.054 (6)*
N1	0.97762 (14)	0.66179 (12)	0.05778 (8)	0.0461 (4)
O1	0.92001 (15)	0.55398 (12)	0.24612 (7)	0.0837 (5)
O2	1.30161 (13)	0.73934 (13)	0.21804 (7)	0.0743 (4)
O3	0.73609 (13)	0.37931 (11)	0.03597 (7)	0.0719 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0384 (11)	0.0552 (10)	0.0466 (10)	−0.0026 (8)	0.0018 (8)	−0.0035 (8)
C2	0.0484 (12)	0.0740 (12)	0.0406 (9)	−0.0126 (10)	0.0011 (8)	−0.0080 (9)
C3	0.0705 (15)	0.0652 (13)	0.0748 (13)	−0.0188 (11)	0.0337 (12)	−0.0210 (10)
C4	0.0688 (14)	0.0615 (12)	0.0749 (13)	0.0125 (11)	0.0328 (12)	0.0059 (10)
C5	0.0434 (12)	0.0802 (13)	0.0527 (11)	0.0004 (10)	0.0108 (9)	−0.0027 (9)
C6	0.0473 (11)	0.0536 (10)	0.0453 (10)	−0.0099 (9)	0.0079 (8)	0.0020 (8)
C7	0.0407 (11)	0.0469 (9)	0.0463 (9)	−0.0020 (8)	0.0023 (8)	−0.0020 (7)
C8	0.0509 (12)	0.0644 (11)	0.0411 (10)	0.0019 (9)	0.0079 (8)	0.0055 (9)
C9	0.0403 (11)	0.0596 (11)	0.0575 (11)	−0.0062 (9)	0.0114 (9)	−0.0097 (9)
C10	0.0566 (13)	0.0667 (12)	0.0722 (13)	−0.0074 (11)	0.0190 (10)	0.0011 (10)
C11	0.0885 (19)	0.0707 (15)	0.1100 (19)	−0.0106 (14)	0.0411 (16)	0.0105 (13)
C12	0.085 (2)	0.0778 (17)	0.141 (2)	−0.0335 (15)	0.0503 (18)	−0.0152 (17)
C13	0.0608 (15)	0.0964 (18)	0.1040 (19)	−0.0290 (14)	0.0232 (13)	−0.0319 (15)
C14	0.0456 (13)	0.0740 (13)	0.0710 (13)	−0.0138 (11)	0.0159 (11)	−0.0201 (11)
C15	0.0416 (11)	0.0620 (11)	0.0441 (10)	−0.0024 (9)	0.0057 (8)	−0.0078 (9)
C16	0.0497 (12)	0.0677 (12)	0.0534 (11)	−0.0044 (10)	0.0100 (9)	−0.0124 (10)
C17	0.0576 (14)	0.0973 (16)	0.0650 (13)	−0.0179 (12)	0.0051 (11)	−0.0303 (13)
C18	0.0680 (17)	0.140 (2)	0.0504 (13)	−0.0093 (16)	−0.0059 (11)	−0.0146 (15)
C19	0.0799 (17)	0.123 (2)	0.0516 (12)	−0.0099 (16)	−0.0059 (12)	0.0122 (13)
C20	0.0629 (14)	0.0857 (14)	0.0490 (11)	−0.0103 (11)	0.0014 (10)	0.0052 (10)
C21	0.119 (2)	0.0863 (17)	0.140 (2)	0.0412 (16)	0.0676 (19)	0.0127 (16)
C22	0.0462 (15)	0.170 (3)	0.0793 (16)	−0.0167 (16)	−0.0019 (13)	−0.0290 (18)
C23	0.088 (2)	0.179 (3)	0.0807 (18)	0.021 (2)	−0.0231 (15)	−0.0037 (19)
C24	0.0777 (16)	0.0658 (13)	0.1047 (18)	−0.0212 (12)	0.0236 (14)	−0.0183 (13)
C25	0.122 (2)	0.0769 (17)	0.147 (3)	−0.0075 (16)	0.029 (2)	0.0255 (17)
N1	0.0390 (9)	0.0585 (9)	0.0413 (8)	−0.0041 (7)	0.0088 (7)	−0.0067 (7)
O1	0.0861 (11)	0.1035 (11)	0.0580 (8)	−0.0004 (9)	0.0049 (7)	0.0331 (8)
O2	0.0478 (9)	0.0991 (11)	0.0686 (9)	−0.0109 (8)	−0.0083 (7)	−0.0111 (8)
O3	0.0709 (10)	0.0583 (8)	0.0812 (9)	−0.0193 (7)	0.0010 (8)	−0.0064 (7)

Geometric parameters (Å, º) top

C1—N1	1.465 (2)	C13—H13	0.9300
C1—C9	1.511 (2)	C14—O2	1.364 (2)
C1—C2	1.556 (2)	C15—C20	1.375 (2)
C1—H1	0.9800	C15—C16	1.395 (2)
C2—C8	1.490 (2)	C16—O3	1.365 (2)
C2—C3	1.525 (3)	C16—C17	1.389 (3)
C2—H2	0.9800	C17—C18	1.372 (3)
C3—C4	1.515 (3)	C17—H17	0.9300
C3—H3A	0.9700	C18—C19	1.360 (3)
C3—H3B	0.9700	C18—H18	0.9300
C4—C5	1.511 (3)	C19—C20	1.381 (3)
C4—C21	1.539 (3)	C19—H19	0.9300
C4—H4	0.9800	C20—H20	0.9300
C5—C6	1.527 (2)	C21—H21A	0.9600
C5—H5A	0.9700	C21—H21B	0.9600
C5—H5B	0.9700	C21—H21C	0.9600
C6—C8	1.495 (2)	C22—O2	1.426 (2)
C6—C7	1.555 (2)	C22—C23	1.493 (4)
C6—H6	0.9800	C22—H22A	0.9700
C7—N1	1.457 (2)	C22—H22B	0.9700
C7—C15	1.517 (2)	C23—H23A	0.9600
C7—H7	0.9800	C23—H23B	0.9600
C8—O1	1.2101 (19)	C23—H23C	0.9600
C9—C10	1.381 (3)	C24—O3	1.436 (2)
C9—C14	1.397 (3)	C24—C25	1.474 (3)
C10—C11	1.382 (3)	C24—H24A	0.9700
C10—H10	0.9300	C24—H24B	0.9700
C11—C12	1.366 (3)	C25—H25A	0.9600
C11—H11	0.9300	C25—H25B	0.9600
C12—C13	1.377 (3)	C25—H25C	0.9600
C12—H12	0.9300	N1—H1N	0.848 (18)
C13—C14	1.388 (3)

N1—C1—C9	110.10 (14)	C12—C13—H13	119.9
N1—C1—C2	109.96 (14)	C14—C13—H13	119.9
C9—C1—C2	111.15 (14)	O2—C14—C13	123.9 (2)
N1—C1—H1	108.5	O2—C14—C9	116.01 (17)
C9—C1—H1	108.5	C13—C14—C9	120.1 (2)
C2—C1—H1	108.5	C20—C15—C16	117.59 (16)
C8—C2—C3	108.30 (15)	C20—C15—C7	122.44 (16)
C8—C2—C1	107.82 (14)	C16—C15—C7	119.90 (15)
C3—C2—C1	115.19 (15)	O3—C16—C17	123.62 (18)
C8—C2—H2	108.5	O3—C16—C15	115.60 (15)
C3—C2—H2	108.5	C17—C16—C15	120.78 (19)
C1—C2—H2	108.5	C18—C17—C16	119.5 (2)
C4—C3—C2	114.42 (15)	C18—C17—H17	120.2
C4—C3—H3A	108.7	C16—C17—H17	120.2
C2—C3—H3A	108.7	C19—C18—C17	120.7 (2)
C4—C3—H3B	108.7	C19—C18—H18	119.7
C2—C3—H3B	108.7	C17—C18—H18	119.7
H3A—C3—H3B	107.6	C18—C19—C20	119.6 (2)
C5—C4—C3	111.43 (15)	C18—C19—H19	120.2
C5—C4—C21	110.60 (18)	C20—C19—H19	120.2
C3—C4—C21	110.98 (18)	C15—C20—C19	121.9 (2)
C5—C4—H4	107.9	C15—C20—H20	119.1
C3—C4—H4	107.9	C19—C20—H20	119.1
C21—C4—H4	107.9	C4—C21—H21A	109.5
C4—C5—C6	115.42 (15)	C4—C21—H21B	109.5
C4—C5—H5A	108.4	H21A—C21—H21B	109.5
C6—C5—H5A	108.4	C4—C21—H21C	109.5
C4—C5—H5B	108.4	H21A—C21—H21C	109.5
C6—C5—H5B	108.4	H21B—C21—H21C	109.5
H5A—C5—H5B	107.5	O2—C22—C23	107.5 (2)
C8—C6—C5	107.99 (14)	O2—C22—H22A	110.2
C8—C6—C7	106.87 (14)	C23—C22—H22A	110.2
C5—C6—C7	115.41 (14)	O2—C22—H22B	110.2
C8—C6—H6	108.8	C23—C22—H22B	110.2
C5—C6—H6	108.8	H22A—C22—H22B	108.5
C7—C6—H6	108.8	C22—C23—H23A	109.5
N1—C7—C15	110.55 (13)	C22—C23—H23B	109.5
N1—C7—C6	110.04 (13)	H23A—C23—H23B	109.5
C15—C7—C6	110.56 (13)	C22—C23—H23C	109.5
N1—C7—H7	108.5	H23A—C23—H23C	109.5
C15—C7—H7	108.5	H23B—C23—H23C	109.5
C6—C7—H7	108.5	O3—C24—C25	108.05 (19)
O1—C8—C2	124.61 (16)	O3—C24—H24A	110.1
O1—C8—C6	123.69 (17)	C25—C24—H24A	110.1
C2—C8—C6	111.70 (14)	O3—C24—H24B	110.1
C10—C9—C14	118.18 (18)	C25—C24—H24B	110.1
C10—C9—C1	122.21 (16)	H24A—C24—H24B	108.4
C14—C9—C1	119.57 (17)	C24—C25—H25A	109.5
C9—C10—C11	121.7 (2)	C24—C25—H25B	109.5
C9—C10—H10	119.1	H25A—C25—H25B	109.5
C11—C10—H10	119.1	C24—C25—H25C	109.5
C12—C11—C10	119.4 (2)	H25A—C25—H25C	109.5
C12—C11—H11	120.3	H25B—C25—H25C	109.5
C10—C11—H11	120.3	C7—N1—C1	115.58 (13)
C11—C12—C13	120.6 (2)	C7—N1—H1N	108.7 (12)
C11—C12—H12	119.7	C1—N1—H1N	106.8 (12)
C13—C12—H12	119.7	C14—O2—C22	119.78 (18)
C12—C13—C14	120.1 (2)	C16—O3—C24	118.36 (16)

N1—C1—C2—C8	54.66 (18)	C11—C12—C13—C14	0.5 (4)
C9—C1—C2—C8	176.83 (14)	C12—C13—C14—O2	179.8 (2)
N1—C1—C2—C3	−66.38 (19)	C12—C13—C14—C9	−0.4 (3)
C9—C1—C2—C3	55.80 (19)	C10—C9—C14—O2	179.74 (17)
C8—C2—C3—C4	−54.3 (2)	C1—C9—C14—O2	2.3 (2)
C1—C2—C3—C4	66.4 (2)	C10—C9—C14—C13	−0.1 (3)
C2—C3—C4—C5	45.8 (2)	C1—C9—C14—C13	−177.49 (17)
C2—C3—C4—C21	169.49 (17)	N1—C7—C15—C20	−17.0 (2)
C3—C4—C5—C6	−45.3 (2)	C6—C7—C15—C20	105.11 (19)
C21—C4—C5—C6	−169.20 (17)	N1—C7—C15—C16	166.35 (16)
C4—C5—C6—C8	52.7 (2)	C6—C7—C15—C16	−71.5 (2)
C4—C5—C6—C7	−66.8 (2)	C20—C15—C16—O3	179.34 (17)
C8—C6—C7—N1	−56.66 (17)	C7—C15—C16—O3	−3.9 (2)
C5—C6—C7—N1	63.43 (17)	C20—C15—C16—C17	0.0 (3)
C8—C6—C7—C15	−179.07 (14)	C7—C15—C16—C17	176.80 (16)
C5—C6—C7—C15	−58.98 (18)	O3—C16—C17—C18	−179.4 (2)
C3—C2—C8—O1	−117.4 (2)	C15—C16—C17—C18	−0.1 (3)
C1—C2—C8—O1	117.36 (19)	C16—C17—C18—C19	0.4 (4)
C3—C2—C8—C6	62.90 (18)	C17—C18—C19—C20	−0.7 (4)
C1—C2—C8—C6	−62.34 (18)	C16—C15—C20—C19	−0.2 (3)
C5—C6—C8—O1	118.6 (2)	C7—C15—C20—C19	−176.98 (18)
C7—C6—C8—O1	−116.67 (19)	C18—C19—C20—C15	0.6 (3)
C5—C6—C8—C2	−61.71 (19)	C15—C7—N1—C1	177.62 (14)
C7—C6—C8—C2	63.03 (18)	C6—C7—N1—C1	55.21 (18)
N1—C1—C9—C10	18.0 (2)	C9—C1—N1—C7	−176.73 (14)
C2—C1—C9—C10	−104.10 (19)	C2—C1—N1—C7	−53.93 (19)
N1—C1—C9—C14	−164.69 (16)	C13—C14—O2—C22	−4.1 (3)
C2—C1—C9—C14	73.2 (2)	C9—C14—O2—C22	176.08 (18)
C14—C9—C10—C11	0.4 (3)	C23—C22—O2—C14	−177.42 (19)
C1—C9—C10—C11	177.78 (18)	C17—C16—O3—C24	−18.1 (3)
C9—C10—C11—C12	−0.3 (3)	C15—C16—O3—C24	162.60 (17)
C10—C11—C12—C13	−0.1 (4)	C25—C24—O3—C16	−167.01 (19)

Experimental details

Crystal data
Chemical formula	C₂₅H₃₁NO₃
M_r	393.51
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	10.3147 (6), 11.8817 (6), 18.7809 (10)
β (°)	100.866 (2)
V (Å³)	2260.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.35 × 0.28 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.974, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	12446, 3876, 2415
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.117, 1.03
No. of reflections	3876
No. of parameters	269
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.13

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).

Acknowledgements

This research was supported by the Corporate-affiliated Research Institute for Academic–Industrial–Institutional Cooperation Improvement (Business No. S7080008110). The authors acknowledge the Department of Chemistry, IIT Madras, for the X-ray data collection.

References

Barker, D., Lin, D. H. S., Carland, J. E., Chu, C. P. Y., Chebib, M., Brimble, M. A., Savage, G. P. & McLeod, M. D. (2005). Bioorg. Med. Chem. 13, 4565–4575. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2004). APEX2, XPREP, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cox, P. J., McCabe, P. H., Milne, N. J. & Sim, G. A. (1985). J. Chem. Soc. Chem. Commun. pp. 626–628. CrossRef Web of Science Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Jeyaraman, R. & Avila, S. (1981). Chem. Rev. 81, 149–174. CrossRef CAS Web of Science Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Padegimas, S. J. & Kovacic, P. (1972). J. Org. Chem. 37, 2672–2676. CrossRef CAS Web of Science Google Scholar
Parthiban, P., Aridoss, G., Rathika, P., Ramkumar, V. & Kabilan, S. (2009a). Bioorg. Med. Chem. Lett. 19, 6981–6985. Web of Science CSD CrossRef PubMed CAS Google Scholar
Parthiban, P., Ramkumar, V., Amirthaganesan, S. & Jeong, Y. T. (2009b). Acta Cryst. E65, o1356. Web of Science CSD CrossRef IUCr Journals Google Scholar
Parthiban, P., Ramkumar, V. & Jeong, Y. T. (2010a). Acta Cryst. E66, o48–o49. Web of Science CSD CrossRef IUCr Journals Google Scholar
Parthiban, P., Ramkumar, V., Kim, M. S., Son, S. M. & Jeong, Y. T. (2009c). Acta Cryst. E65, o1383. Web of Science CSD CrossRef IUCr Journals Google Scholar
Parthiban, P., Rathika, P., Park, K. S. & Jeong, Y. T. (2010b). Monatsh. Chem. 141, 79–93. Web of Science CrossRef CAS Google Scholar
Parthiban, P., Rathika, P., Ramkumar, V., Son, S. M. & Jeong, Y. T. (2010c). Bioorg. Med. Chem. Lett. 20, 1642–1647. Web of Science CSD CrossRef CAS PubMed Google Scholar
Parthiban, P., Subalakshmi, V., Balasubramanian, K., Islam, Md. N., Choi, J. S. & Jeong, Y. T. (2011). Bioorg. Med. Chem. Lett. 21, 2287–2296. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Smith-Verdier, P., Florencio, F. & García-Blanco, S. (1983). Acta Cryst. C39, 101–103. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar