organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

aDepartment of Biomedicinal Chemistry, Inje University, Gimhae, Gyeongnam 621 749, Republic of Korea, and bDepartment of Chemistry, IIT Madras, Chennai 600 036, TamilNadu, India
*Correspondence e-mail: parthisivam@yahoo.co.in

(Received 19 September 2012; accepted 30 October 2012; online 3 November 2012)

The asymmetric unit of the title compound, C24H29NO3, contains two independent mol­ecules, which each exibit a twin-chair conformation with an equatorial orientation of the ortho-eth­oxy­phenyl groups but different dihedral angles [41.3 (1) and 24.1 (1)°] between the benzene rings. In the crystal, pairs of weak C—H⋯O hydrogen bonds link the two different independent mol­ecules into dimers.

Related literature

For the synthesis and stereochemistry of 3-aza­bicyclo­[3.3.1]nonan-9-ones, see: Park et al. (2011[Park, D. H., Jeong, Y. T. & Parthiban, P. (2011). J. Mol. Struct. 1005, 31-44.]) and for their biological properties, see: Jeyaraman & Avila (1981[Jeyaraman, R. & Avila, S. (1981). Chem. Rev. 81, 149-174.]); Park et al. (2012a[Park, D. H., Venkatesn, J., Kim, S. K. & Prthiban, P. (2012a). Bioorg. Med. Chem. Lett. 22, 6004-6009.]); Parthiban et al. (2010a[Parthiban, P., Rathika, P., Ramkumar, V., Son, S. M. & Jeong, Y. T. (2010a). Bioorg. Med. Chem. Lett. 20, 1642-1647.],b[Parthiban, P., Rathika, P., Park, K. S. & Jeong, Y. T. (2010b). Monatsh. Chem. 141, 79-93.]; 2011a[Parthiban, P., Subalakshmi, V., Balasubramanian, K., Islam, Md. N., Choi, J. S. & Jeong, Y. T. (2011a). Bioorg. Med. Chem. Lett. 21, 2287-2296.]). For similar structures, see: Park et al. (2012b[Park, D. H., Ramkumar, V. & Parthiban, P. (2012b). Acta Cryst. E68, o2841.]); Parthiban et al. (2009a[Parthiban, P., Ramkumar, V., Kim, M. S., Son, S. M. & Jeong, Y. T. (2009a). Acta Cryst. E65, o1383.],b[Parthiban, P., Ramkumar, V. & Jeong, Y. T. (2009b). Acta Cryst. E65, o3103.]; 2011b[Parthiban, P., Ramkumar, V., Park, D. H. & Jeong, Y. T. (2011b). Acta Cryst. E67, o1475-o1476.]). For conformational analysis, see: Kalsi (1997[Kalsi, P. S. (1997). In Stereochemistry: Conformation and Mechanism. New Delhi: New Age International (P) Ltd.]); Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C24H29NO3

  • Mr = 379.49

  • Triclinic, [P \overline 1]

  • a = 9.7981 (3) Å

  • b = 13.6139 (5) Å

  • c = 16.7098 (6) Å

  • α = 74.363 (2)°

  • β = 80.464 (2)°

  • γ = 83.563 (2)°

  • V = 2111.42 (13) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 298 K

  • 0.35 × 0.28 × 0.22 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.983

  • 27579 measured reflections

  • 9839 independent reflections

  • 6037 reflections with I > 2σ(I)

  • Rint = 0.022

Refinement
  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.150

  • S = 1.02

  • 9839 reflections

  • 509 parameters

  • H-atom parameters constrained

  • Δρmax = 0.53 e Å−3

  • Δρmin = −0.45 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C23—H23A⋯O1A 0.97 2.42 3.311 (3) 153
C23A—H23C⋯O1 0.97 2.43 3.297 (3) 149

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Nitrogen containing heterocycles are useful building-blocks of the construction of various pharmacologically important molecules. Since the 3-azabicyclononanes are displying diverse biological actions (Park et al., 2012a; Parthiban et al., 2010a, 2010b, 2011a; Jeyaraman & Avila, 1981), and the biological actions mainly depend on the stereochemistry of the molecules, the synthesis as well as stereochemical analysis of any biologically active molecules are of importance in the drug-design and drug-devlopement programs. Based on the above points, we synthesized the title compound, in order to examine the configurational and conformational status by single-crystal X-ray studies.

Careful examination of the asymmery parameters and torsion angles of the title compound reveal that the values are similar to its analogous compounds (Parthiban et al., 2009a, 2009b, 2011b; Park et al. 2012b). 2,4-Bis(4-ethoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one is the positional isomer of the title compound that exists in the twin-chair conformation. The impotant torsion angles of the title compound, viz., C2—C8—C6—C7 (-58.8 (2)°), C1—C2—C8—C6 (60.8 (2)°), C2—C8—C6—C5 (65.9 (2)°) and C3—C2—C8—C6 (-63.8 (2)°) insist that the bicycle exists in twin-chair conformation. However, the cyclohexanone torsion angles are more deviated than the piperidone ring as well as well the ideal chair cyclohexanone torsion angle of 56° (Kalsi, 1997). The comparision of above with the corresponding torsion angles of the para-isomer [-62.5 (2), 62.3 (2), 62.6 (2) and -62.6 (2)°, respectively] indicate that in the title compound, the cyclohexnone ring is more flattened than the cyclohexanone of its para-isomer. The above stereochemistry is further witnessed by the Cremer & Pople (1975) ring puckering parameters. For the piperidone ring of the title compound, the total puckering amplitude, QT is 0.5970 Å and the phase angle θ is 176.66°, for the cyclohexanone, QT = 0.5590 Å and θ = 163.39°. The same for the para-isomer are, QT = 0.5999 Å and θ = 173.84° (piperidone) and QT = 0.5643 Å and θ = 168.44°(cyclohexanone). Further, the orientation of the ethoxyphenyl groups on both sides of the secondary amino group are identified by their torsion angles. The torsion angle of C8—C2—C1—C9 and C8—C6—C7—C17 are 176.24 (15) and -179.42 (15)°, respectively.

The two benzene rings in two independent molecules are inclined to each other with angles of 41.3 (1) and 24.1 (1)°, respectively. In the crystal, weak intermolecular C—H···O interactions (Table 1) link independent molecules into dimer.

Related literature top

For the synthesis and stereochemistry of 3-azabicyclo[3.3.1]nonan-9-ones, see: Park et al. (2011) and for their biological properties, see: Jeyaraman & Avila (1981); Park et al. (2012a); Parthiban et al. (2010a,b; 2011a). For similar structures, see: Park et al. (2012b); Parthiban et al. (2009a,b; 2011b). For conformational analysis, see: Kalsi (1997); Cremer & Pople (1975).

Experimental top

The 2,4-bis(2-ethoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one was synthesized by a modified and an optimized double Mannich condensation in one-pot, using 2-ethoxybenzaldehyde (0.1 mol, 15.018 g/13.94 ml), cyclohexanone (0.05 mol, 4.90 g/5.18 ml) and ammonium acetate (0.075 mol, 5.78 g) in a 50 ml of absolute ethanol (Park et al., 2011). 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. After completion of the rection, the crude compound 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.

Refinement top

All hydrogen atoms were fixed geometrically and allowed to ride on the parent carbon atoms, with C—H = 0.93–0.98 Å and N—H = 0.86 Å, and with Uiso(H) = 1.2–1.5Ueq of the parent atom.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (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
[Figure 1] Fig. 1. Two independent molecules of the title compound with atomic labels and displacement ellipsoids represented with 30% probability level. H atoms omitted for clarity.
2,4-Bis(2-ethoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one top
Crystal data top
C24H29NO3Z = 4
Mr = 379.49F(000) = 816
Triclinic, P1Dx = 1.194 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.7981 (3) ÅCell parameters from 5334 reflections
b = 13.6139 (5) Åθ = 0.0–0.0°
c = 16.7098 (6) ŵ = 0.08 mm1
α = 74.363 (2)°T = 298 K
β = 80.464 (2)°Block, colourless
γ = 83.563 (2)°0.35 × 0.28 × 0.22 mm
V = 2111.42 (13) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer
9839 independent reflections
Radiation source: fine-focus sealed tube6037 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
phi and ω scansθmax = 28.6°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 1212
Tmin = 0.973, Tmax = 0.983k = 1718
27579 measured reflectionsl = 2122
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0546P)2 + 0.6801P]
where P = (Fo2 + 2Fc2)/3
9839 reflections(Δ/σ)max < 0.001
509 parametersΔρmax = 0.53 e Å3
0 restraintsΔρmin = 0.45 e Å3
Crystal data top
C24H29NO3γ = 83.563 (2)°
Mr = 379.49V = 2111.42 (13) Å3
Triclinic, P1Z = 4
a = 9.7981 (3) ÅMo Kα radiation
b = 13.6139 (5) ŵ = 0.08 mm1
c = 16.7098 (6) ÅT = 298 K
α = 74.363 (2)°0.35 × 0.28 × 0.22 mm
β = 80.464 (2)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
9839 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
6037 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.983Rint = 0.022
27579 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.150H-atom parameters constrained
S = 1.02Δρmax = 0.53 e Å3
9839 reflectionsΔρmin = 0.45 e Å3
509 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
xyzUiso*/Ueq
C10.36743 (18)0.85897 (14)0.06351 (11)0.0500 (4)
H10.41780.84880.01030.060*
C20.25640 (19)0.77992 (14)0.09612 (12)0.0533 (4)
H20.19370.79010.05410.064*
C30.1701 (2)0.78294 (16)0.18078 (13)0.0647 (5)
H3A0.13210.85260.17780.078*
H3B0.09270.74060.19020.078*
C40.2490 (2)0.74703 (17)0.25537 (13)0.0695 (6)
H4A0.30190.80220.25740.083*
H4B0.18280.73220.30630.083*
C50.3472 (2)0.65312 (15)0.25377 (13)0.0616 (5)
H5A0.29400.59310.27130.074*
H5B0.41070.64620.29410.074*
C60.4315 (2)0.65624 (14)0.16746 (12)0.0536 (5)
H60.48110.58920.16920.064*
C70.53772 (18)0.73929 (14)0.13630 (11)0.0488 (4)
H70.58810.73230.08210.059*
C80.3305 (2)0.67594 (15)0.10576 (13)0.0586 (5)
C90.29786 (19)0.96590 (14)0.04698 (13)0.0554 (5)
C100.2861 (2)1.02513 (16)0.10223 (16)0.0747 (6)
H100.32721.00120.15080.090*
C110.2138 (3)1.12062 (19)0.0872 (2)0.0993 (9)
H110.20601.16040.12530.119*
C120.1538 (3)1.15537 (18)0.0147 (2)0.0938 (9)
H120.10571.21940.00390.113*
C130.1635 (2)1.09799 (18)0.04144 (17)0.0791 (7)
H130.12151.12240.08970.095*
C140.2359 (2)1.00353 (16)0.02670 (14)0.0635 (5)
C150.1763 (3)0.9619 (2)0.14731 (16)0.0920 (8)
H15A0.20421.02450.18790.110*
H15B0.07770.97000.12820.110*
C160.2073 (4)0.8738 (3)0.1860 (2)0.1269 (12)
H16A0.30500.86700.20500.190*
H16B0.15710.88540.23270.190*
H16C0.17990.81230.14510.190*
C170.64188 (18)0.72424 (14)0.19648 (11)0.0486 (4)
C180.75334 (18)0.65048 (14)0.19377 (11)0.0505 (4)
C190.8500 (2)0.63614 (16)0.24840 (12)0.0581 (5)
H190.92450.58780.24600.070*
C200.8364 (2)0.69305 (18)0.30616 (13)0.0651 (6)
H200.90170.68280.34270.078*
C210.7274 (2)0.76473 (18)0.31044 (13)0.0671 (6)
H210.71790.80280.34990.081*
C220.6315 (2)0.77980 (16)0.25514 (12)0.0585 (5)
H220.55800.82890.25780.070*
C230.8671 (2)0.51955 (16)0.12899 (14)0.0691 (6)
H23A0.87440.47330.18380.083*
H23B0.95480.55040.10760.083*
C240.8344 (3)0.4629 (2)0.0709 (2)0.1067 (10)
H24A0.74820.43190.09300.160*
H24B0.90710.41080.06500.160*
H24C0.82670.50940.01700.160*
C1A0.64687 (16)0.15039 (12)0.44479 (10)0.0422 (4)
H1A0.65610.12040.39680.051*
C2A0.76566 (17)0.22198 (13)0.42932 (11)0.0473 (4)
H2A0.85450.18180.42310.057*
C3A0.7659 (2)0.27739 (14)0.49824 (12)0.0556 (5)
H3A10.76190.22700.55200.067*
H3A20.85290.30930.48830.067*
C4A0.6469 (2)0.35883 (15)0.50361 (12)0.0602 (5)
H4A10.66890.40240.53640.072*
H4A20.56360.32560.53290.072*
C5A0.6178 (2)0.42519 (14)0.41788 (13)0.0589 (5)
H5A10.68780.47450.39660.071*
H5A20.52850.46300.42470.071*
C6A0.61683 (18)0.36447 (13)0.35247 (11)0.0484 (4)
H6A0.61120.41280.29760.058*
C7A0.50066 (17)0.28949 (12)0.37073 (10)0.0426 (4)
H7A0.51360.25570.32480.051*
C8A0.75265 (18)0.30110 (14)0.34832 (12)0.0496 (4)
C9A0.65574 (18)0.06396 (12)0.52316 (11)0.0450 (4)
C10A0.5745 (2)0.06544 (14)0.59797 (12)0.0576 (5)
H10A0.50970.12030.60070.069*
C11A0.5869 (3)0.01343 (16)0.66985 (13)0.0712 (6)
H11A0.53040.01160.72000.085*
C12A0.6830 (3)0.09377 (15)0.66610 (15)0.0729 (6)
H12A0.69260.14610.71430.087*
C13A0.7656 (2)0.09789 (14)0.59183 (15)0.0638 (6)
H13A0.83010.15310.58980.077*
C14A0.75241 (19)0.01967 (12)0.52014 (12)0.0503 (4)
C15A0.9384 (2)0.09232 (16)0.43565 (16)0.0736 (7)
H15C0.90270.15940.44970.088*
H15D1.00420.09330.47340.088*
C16A1.0074 (3)0.0658 (2)0.34722 (17)0.0906 (8)
H16D0.94440.07230.31090.136*
H16E1.08850.11140.34130.136*
H16F1.03390.00330.33230.136*
C17A0.35634 (17)0.34232 (12)0.37438 (10)0.0419 (4)
C18A0.28975 (18)0.36874 (12)0.30268 (11)0.0451 (4)
C19A0.15377 (19)0.41012 (14)0.30671 (13)0.0563 (5)
H19A0.10860.42490.25960.068*
C20A0.0859 (2)0.42923 (15)0.37999 (14)0.0643 (6)
H20A0.00520.45740.38220.077*
C21A0.1504 (2)0.40738 (16)0.45031 (13)0.0637 (5)
H21A0.10460.42240.49950.076*
C22A0.28471 (19)0.36263 (14)0.44692 (12)0.0538 (5)
H22A0.32760.34590.49500.065*
C23A0.3037 (2)0.36747 (16)0.15767 (12)0.0666 (6)
H23C0.26750.43810.14080.080*
H23D0.22780.32370.16770.080*
C24A0.4124 (3)0.3436 (2)0.09121 (15)0.1005 (9)
H24D0.48360.39070.07900.151*
H24E0.37190.34960.04140.151*
H24F0.45200.27510.11020.151*
N10.46630 (15)0.84156 (11)0.12323 (9)0.0500 (4)
H1B0.48090.88640.14800.060*
N1A0.51362 (13)0.21006 (10)0.44872 (8)0.0422 (3)
H1A10.45020.19980.49170.051*
O10.3081 (2)0.61501 (12)0.06929 (11)0.0909 (5)
O20.25195 (18)0.94051 (14)0.07861 (10)0.0878 (5)
O30.75755 (14)0.59694 (11)0.13539 (9)0.0661 (4)
O1A0.84094 (15)0.31195 (12)0.28738 (9)0.0741 (4)
O2A0.82815 (14)0.01692 (10)0.44357 (9)0.0644 (4)
O3A0.36692 (14)0.35032 (10)0.23189 (8)0.0589 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0456 (10)0.0543 (10)0.0472 (10)0.0013 (8)0.0110 (8)0.0063 (8)
C20.0506 (10)0.0540 (11)0.0582 (11)0.0054 (8)0.0189 (9)0.0116 (9)
C30.0476 (11)0.0613 (12)0.0793 (15)0.0091 (9)0.0014 (10)0.0105 (11)
C40.0655 (13)0.0780 (14)0.0604 (13)0.0117 (11)0.0062 (10)0.0165 (11)
C50.0645 (12)0.0567 (11)0.0587 (12)0.0146 (10)0.0085 (10)0.0025 (9)
C60.0604 (11)0.0431 (9)0.0590 (11)0.0024 (8)0.0152 (9)0.0143 (8)
C70.0473 (10)0.0551 (10)0.0418 (9)0.0023 (8)0.0075 (8)0.0106 (8)
C80.0666 (13)0.0530 (11)0.0600 (12)0.0098 (9)0.0135 (10)0.0162 (9)
C90.0470 (10)0.0486 (10)0.0663 (12)0.0060 (8)0.0142 (9)0.0028 (9)
C100.0813 (15)0.0523 (12)0.0957 (17)0.0022 (11)0.0362 (13)0.0146 (12)
C110.116 (2)0.0553 (14)0.139 (3)0.0024 (14)0.049 (2)0.0305 (15)
C120.0855 (18)0.0458 (12)0.140 (3)0.0024 (12)0.0352 (17)0.0019 (15)
C130.0705 (15)0.0619 (14)0.0921 (18)0.0055 (11)0.0250 (13)0.0106 (13)
C140.0512 (11)0.0592 (12)0.0702 (14)0.0024 (9)0.0175 (10)0.0052 (11)
C150.0973 (19)0.0965 (19)0.0769 (16)0.0138 (15)0.0428 (14)0.0078 (14)
C160.162 (3)0.133 (3)0.100 (2)0.015 (2)0.057 (2)0.041 (2)
C170.0442 (10)0.0558 (10)0.0414 (9)0.0019 (8)0.0066 (7)0.0052 (8)
C180.0470 (10)0.0554 (10)0.0417 (10)0.0013 (8)0.0052 (8)0.0015 (8)
C190.0463 (10)0.0652 (12)0.0538 (11)0.0013 (9)0.0092 (9)0.0010 (10)
C200.0511 (12)0.0883 (15)0.0521 (12)0.0092 (11)0.0147 (9)0.0056 (11)
C210.0571 (12)0.0916 (16)0.0579 (12)0.0059 (11)0.0111 (10)0.0261 (11)
C220.0492 (11)0.0708 (13)0.0559 (11)0.0002 (9)0.0092 (9)0.0172 (10)
C230.0626 (13)0.0655 (13)0.0713 (14)0.0150 (10)0.0071 (11)0.0133 (11)
C240.108 (2)0.103 (2)0.124 (2)0.0248 (17)0.0270 (19)0.0614 (19)
C1A0.0416 (9)0.0383 (8)0.0458 (9)0.0075 (7)0.0142 (7)0.0083 (7)
C2A0.0358 (9)0.0492 (10)0.0518 (10)0.0056 (7)0.0110 (7)0.0050 (8)
C3A0.0541 (11)0.0552 (11)0.0580 (11)0.0090 (9)0.0212 (9)0.0052 (9)
C4A0.0675 (13)0.0555 (11)0.0641 (13)0.0064 (10)0.0174 (10)0.0208 (10)
C5A0.0560 (11)0.0425 (10)0.0771 (14)0.0019 (8)0.0147 (10)0.0108 (9)
C6A0.0466 (10)0.0443 (9)0.0452 (10)0.0034 (8)0.0100 (8)0.0037 (8)
C7A0.0428 (9)0.0427 (9)0.0412 (9)0.0071 (7)0.0144 (7)0.0079 (7)
C8A0.0421 (10)0.0531 (10)0.0502 (11)0.0038 (8)0.0078 (8)0.0064 (8)
C9A0.0457 (9)0.0381 (9)0.0504 (10)0.0002 (7)0.0169 (8)0.0054 (7)
C10A0.0653 (12)0.0477 (10)0.0550 (12)0.0000 (9)0.0130 (10)0.0038 (9)
C11A0.0909 (16)0.0619 (13)0.0550 (12)0.0117 (12)0.0132 (11)0.0008 (10)
C12A0.1019 (18)0.0451 (11)0.0682 (15)0.0135 (12)0.0378 (13)0.0100 (10)
C13A0.0768 (14)0.0348 (9)0.0820 (15)0.0025 (9)0.0395 (12)0.0045 (10)
C14A0.0511 (10)0.0382 (9)0.0642 (12)0.0023 (8)0.0258 (9)0.0091 (8)
C15A0.0755 (14)0.0576 (12)0.1014 (18)0.0314 (11)0.0464 (13)0.0378 (12)
C16A0.0789 (16)0.105 (2)0.100 (2)0.0374 (15)0.0292 (15)0.0553 (16)
C17A0.0396 (9)0.0363 (8)0.0480 (10)0.0039 (7)0.0129 (7)0.0064 (7)
C18A0.0473 (10)0.0348 (8)0.0513 (10)0.0008 (7)0.0163 (8)0.0036 (7)
C19A0.0483 (11)0.0501 (10)0.0670 (13)0.0043 (8)0.0256 (10)0.0016 (9)
C20A0.0410 (10)0.0598 (12)0.0801 (15)0.0105 (9)0.0118 (10)0.0011 (11)
C21A0.0517 (11)0.0672 (13)0.0613 (12)0.0137 (10)0.0016 (9)0.0089 (10)
C22A0.0496 (10)0.0565 (11)0.0526 (11)0.0085 (9)0.0146 (9)0.0100 (9)
C23A0.0905 (16)0.0575 (12)0.0560 (12)0.0004 (11)0.0338 (11)0.0100 (10)
C24A0.122 (2)0.126 (2)0.0593 (15)0.0061 (19)0.0238 (15)0.0328 (15)
N10.0488 (8)0.0465 (8)0.0555 (9)0.0023 (7)0.0180 (7)0.0085 (7)
N1A0.0365 (7)0.0422 (7)0.0420 (8)0.0067 (6)0.0079 (6)0.0033 (6)
O10.1271 (15)0.0672 (10)0.0981 (12)0.0053 (9)0.0477 (11)0.0361 (9)
O20.0957 (12)0.1031 (13)0.0630 (10)0.0266 (10)0.0349 (9)0.0180 (9)
O30.0636 (9)0.0718 (9)0.0633 (9)0.0197 (7)0.0188 (7)0.0218 (7)
O1A0.0576 (8)0.0869 (11)0.0582 (9)0.0040 (8)0.0064 (7)0.0023 (8)
O2A0.0614 (8)0.0535 (8)0.0740 (10)0.0239 (6)0.0188 (7)0.0146 (7)
O3A0.0659 (8)0.0636 (8)0.0467 (7)0.0129 (7)0.0236 (6)0.0106 (6)
Geometric parameters (Å, º) top
C1—N11.460 (2)C1A—C9A1.514 (2)
C1—C91.511 (3)C1A—C2A1.546 (2)
C1—C21.545 (3)C1A—H1A0.9800
C1—H10.9800C2A—C8A1.500 (2)
C2—C81.497 (3)C2A—C3A1.538 (3)
C2—C31.531 (3)C2A—H2A0.9800
C2—H20.9800C3A—C4A1.525 (3)
C3—C41.516 (3)C3A—H3A10.9700
C3—H3A0.9700C3A—H3A20.9700
C3—H3B0.9700C4A—C5A1.526 (3)
C4—C51.515 (3)C4A—H4A10.9700
C4—H4A0.9700C4A—H4A20.9700
C4—H4B0.9700C5A—C6A1.540 (3)
C5—C61.531 (3)C5A—H5A10.9700
C5—H5A0.9700C5A—H5A20.9700
C5—H5B0.9700C6A—C8A1.505 (2)
C6—C81.498 (3)C6A—C7A1.552 (2)
C6—C71.549 (3)C6A—H6A0.9800
C6—H60.9800C7A—N1A1.466 (2)
C7—N11.464 (2)C7A—C17A1.513 (2)
C7—C171.509 (2)C7A—H7A0.9800
C7—H70.9800C8A—O1A1.210 (2)
C8—O11.210 (2)C9A—C10A1.370 (3)
C9—C101.364 (3)C9A—C14A1.403 (2)
C9—C141.409 (3)C10A—C11A1.391 (3)
C10—C111.390 (3)C10A—H10A0.9300
C10—H100.9300C11A—C12A1.368 (3)
C11—C121.380 (4)C11A—H11A0.9300
C11—H110.9300C12A—C13A1.376 (3)
C12—C131.359 (4)C12A—H12A0.9300
C12—H120.9300C13A—C14A1.385 (3)
C13—C141.378 (3)C13A—H13A0.9300
C13—H130.9300C14A—O2A1.362 (2)
C14—O21.356 (3)C15A—O2A1.420 (2)
C15—O21.416 (3)C15A—C16A1.485 (3)
C15—C161.489 (4)C15A—H15C0.9700
C15—H15A0.9700C15A—H15D0.9700
C15—H15B0.9700C16A—H16D0.9600
C16—H16A0.9600C16A—H16E0.9600
C16—H16B0.9600C16A—H16F0.9600
C16—H16C0.9600C17A—C22A1.376 (2)
C17—C221.376 (3)C17A—C18A1.402 (2)
C17—C181.402 (2)C18A—O3A1.362 (2)
C18—O31.359 (2)C18A—C19A1.385 (2)
C18—C191.385 (3)C19A—C20A1.369 (3)
C19—C201.374 (3)C19A—H19A0.9300
C19—H190.9300C20A—C21A1.373 (3)
C20—C211.370 (3)C20A—H20A0.9300
C20—H200.9300C21A—C22A1.386 (3)
C21—C221.386 (3)C21A—H21A0.9300
C21—H210.9300C22A—H22A0.9300
C22—H220.9300C23A—O3A1.429 (2)
C23—O31.429 (2)C23A—C24A1.482 (3)
C23—C241.484 (3)C23A—H23C0.9700
C23—H23A0.9700C23A—H23D0.9700
C23—H23B0.9700C24A—H24D0.9600
C24—H24A0.9600C24A—H24E0.9600
C24—H24B0.9600C24A—H24F0.9600
C24—H24C0.9600N1—H1B0.8600
C1A—N1A1.460 (2)N1A—H1A10.8600
N1—C1—C9112.73 (15)C2A—C1A—H1A108.0
N1—C1—C2109.67 (14)C8A—C2A—C3A108.26 (15)
C9—C1—C2109.74 (14)C8A—C2A—C1A107.36 (13)
N1—C1—H1108.2C3A—C2A—C1A115.16 (15)
C9—C1—H1108.2C8A—C2A—H2A108.6
C2—C1—H1108.2C3A—C2A—H2A108.6
C8—C2—C3107.69 (16)C1A—C2A—H2A108.6
C8—C2—C1107.31 (15)C4A—C3A—C2A114.66 (15)
C3—C2—C1115.21 (16)C4A—C3A—H3A1108.6
C8—C2—H2108.8C2A—C3A—H3A1108.6
C3—C2—H2108.8C4A—C3A—H3A2108.6
C1—C2—H2108.8C2A—C3A—H3A2108.6
C4—C3—C2114.79 (16)H3A1—C3A—H3A2107.6
C4—C3—H3A108.6C3A—C4A—C5A113.24 (17)
C2—C3—H3A108.6C3A—C4A—H4A1108.9
C4—C3—H3B108.6C5A—C4A—H4A1108.9
C2—C3—H3B108.6C3A—C4A—H4A2108.9
H3A—C3—H3B107.5C5A—C4A—H4A2108.9
C5—C4—C3114.22 (18)H4A1—C4A—H4A2107.7
C5—C4—H4A108.7C4A—C5A—C6A113.95 (15)
C3—C4—H4A108.7C4A—C5A—H5A1108.8
C5—C4—H4B108.7C6A—C5A—H5A1108.8
C3—C4—H4B108.7C4A—C5A—H5A2108.8
H4A—C4—H4B107.6C6A—C5A—H5A2108.8
C4—C5—C6113.58 (16)H5A1—C5A—H5A2107.7
C4—C5—H5A108.8C8A—C6A—C5A107.13 (15)
C6—C5—H5A108.8C8A—C6A—C7A106.65 (14)
C4—C5—H5B108.8C5A—C6A—C7A116.51 (15)
C6—C5—H5B108.8C8A—C6A—H6A108.8
H5A—C5—H5B107.7C5A—C6A—H6A108.8
C8—C6—C5107.26 (16)C7A—C6A—H6A108.8
C8—C6—C7108.30 (15)N1A—C7A—C17A110.19 (13)
C5—C6—C7115.01 (15)N1A—C7A—C6A110.42 (13)
C8—C6—H6108.7C17A—C7A—C6A113.17 (13)
C5—C6—H6108.7N1A—C7A—H7A107.6
C7—C6—H6108.7C17A—C7A—H7A107.6
N1—C7—C17111.45 (14)C6A—C7A—H7A107.6
N1—C7—C6110.49 (14)O1A—C8A—C2A123.74 (16)
C17—C7—C6110.87 (14)O1A—C8A—C6A124.56 (16)
N1—C7—H7108.0C2A—C8A—C6A111.70 (15)
C17—C7—H7108.0C10A—C9A—C14A118.50 (16)
C6—C7—H7108.0C10A—C9A—C1A122.21 (15)
O1—C8—C2123.55 (19)C14A—C9A—C1A119.28 (16)
O1—C8—C6124.69 (19)C9A—C10A—C11A121.32 (19)
C2—C8—C6111.73 (15)C9A—C10A—H10A119.3
C10—C9—C14118.76 (19)C11A—C10A—H10A119.3
C10—C9—C1122.92 (18)C12A—C11A—C10A119.4 (2)
C14—C9—C1118.23 (18)C12A—C11A—H11A120.3
C9—C10—C11121.2 (2)C10A—C11A—H11A120.3
C9—C10—H10119.4C11A—C12A—C13A120.68 (19)
C11—C10—H10119.4C11A—C12A—H12A119.7
C12—C11—C10118.8 (3)C13A—C12A—H12A119.7
C12—C11—H11120.6C12A—C13A—C14A119.83 (19)
C10—C11—H11120.6C12A—C13A—H13A120.1
C13—C12—C11121.3 (2)C14A—C13A—H13A120.1
C13—C12—H12119.3O2A—C14A—C13A124.40 (17)
C11—C12—H12119.3O2A—C14A—C9A115.37 (15)
C12—C13—C14119.9 (2)C13A—C14A—C9A120.23 (19)
C12—C13—H13120.1O2A—C15A—C16A107.61 (18)
C14—C13—H13120.1O2A—C15A—H15C110.2
O2—C14—C13124.5 (2)C16A—C15A—H15C110.2
O2—C14—C9115.44 (18)O2A—C15A—H15D110.2
C13—C14—C9120.1 (2)C16A—C15A—H15D110.2
O2—C15—C16107.1 (2)H15C—C15A—H15D108.5
O2—C15—H15A110.3C15A—C16A—H16D109.5
C16—C15—H15A110.3C15A—C16A—H16E109.5
O2—C15—H15B110.3H16D—C16A—H16E109.5
C16—C15—H15B110.3C15A—C16A—H16F109.5
H15A—C15—H15B108.6H16D—C16A—H16F109.5
C15—C16—H16A109.5H16E—C16A—H16F109.5
C15—C16—H16B109.5C22A—C17A—C18A118.05 (15)
H16A—C16—H16B109.5C22A—C17A—C7A122.34 (15)
C15—C16—H16C109.5C18A—C17A—C7A119.57 (15)
H16A—C16—H16C109.5O3A—C18A—C19A124.10 (16)
H16B—C16—H16C109.5O3A—C18A—C17A115.66 (14)
C22—C17—C18118.06 (17)C19A—C18A—C17A120.25 (17)
C22—C17—C7122.51 (16)C20A—C19A—C18A119.99 (18)
C18—C17—C7119.43 (16)C20A—C19A—H19A120.0
O3—C18—C19124.35 (17)C18A—C19A—H19A120.0
O3—C18—C17115.60 (16)C19A—C20A—C21A120.89 (18)
C19—C18—C17120.05 (18)C19A—C20A—H20A119.6
C20—C19—C18120.28 (19)C21A—C20A—H20A119.6
C20—C19—H19119.9C20A—C21A—C22A118.97 (19)
C18—C19—H19119.9C20A—C21A—H21A120.5
C21—C20—C19120.57 (19)C22A—C21A—H21A120.5
C21—C20—H20119.7C17A—C22A—C21A121.78 (17)
C19—C20—H20119.7C17A—C22A—H22A119.1
C20—C21—C22119.1 (2)C21A—C22A—H22A119.1
C20—C21—H21120.4O3A—C23A—C24A107.22 (18)
C22—C21—H21120.4O3A—C23A—H23C110.3
C17—C22—C21121.93 (19)C24A—C23A—H23C110.3
C17—C22—H22119.0O3A—C23A—H23D110.3
C21—C22—H22119.0C24A—C23A—H23D110.3
O3—C23—C24107.78 (19)H23C—C23A—H23D108.5
O3—C23—H23A110.2C23A—C24A—H24D109.5
C24—C23—H23A110.2C23A—C24A—H24E109.5
O3—C23—H23B110.2H24D—C24A—H24E109.5
C24—C23—H23B110.2C23A—C24A—H24F109.5
H23A—C23—H23B108.5H24D—C24A—H24F109.5
C23—C24—H24A109.5H24E—C24A—H24F109.5
C23—C24—H24B109.5C1—N1—C7112.51 (14)
H24A—C24—H24B109.5C1—N1—H1B123.7
C23—C24—H24C109.5C7—N1—H1B123.7
H24A—C24—H24C109.5C1A—N1A—C7A112.04 (13)
H24B—C24—H24C109.5C1A—N1A—H1A1124.0
N1A—C1A—C9A111.76 (14)C7A—N1A—H1A1124.0
N1A—C1A—C2A109.47 (13)C14—O2—C15120.69 (19)
C9A—C1A—C2A111.38 (13)C18—O3—C23119.19 (15)
N1A—C1A—H1A108.0C14A—O2A—C15A119.74 (16)
C9A—C1A—H1A108.0C18A—O3A—C23A119.32 (15)
N1—C1—C2—C859.41 (19)C8A—C6A—C7A—N1A57.59 (17)
C9—C1—C2—C8176.24 (15)C5A—C6A—C7A—N1A61.93 (18)
N1—C1—C2—C360.5 (2)C8A—C6A—C7A—C17A178.36 (14)
C9—C1—C2—C363.9 (2)C5A—C6A—C7A—C17A62.12 (19)
C8—C2—C3—C450.3 (2)C3A—C2A—C8A—O1A116.7 (2)
C1—C2—C3—C469.4 (2)C1A—C2A—C8A—O1A118.4 (2)
C2—C3—C4—C541.6 (2)C3A—C2A—C8A—C6A63.49 (19)
C3—C4—C5—C643.3 (2)C1A—C2A—C8A—C6A61.42 (19)
C4—C5—C6—C853.8 (2)C5A—C6A—C8A—O1A115.0 (2)
C4—C5—C6—C766.7 (2)C7A—C6A—C8A—O1A119.6 (2)
C8—C6—C7—N155.34 (19)C5A—C6A—C8A—C2A65.14 (19)
C5—C6—C7—N164.60 (19)C7A—C6A—C8A—C2A60.28 (18)
C8—C6—C7—C17179.42 (15)N1A—C1A—C9A—C10A22.4 (2)
C5—C6—C7—C1759.5 (2)C2A—C1A—C9A—C10A100.38 (19)
C3—C2—C8—O1114.5 (2)N1A—C1A—C9A—C14A159.10 (15)
C1—C2—C8—O1120.9 (2)C2A—C1A—C9A—C14A78.10 (19)
C3—C2—C8—C663.8 (2)C14A—C9A—C10A—C11A0.3 (3)
C1—C2—C8—C660.8 (2)C1A—C9A—C10A—C11A178.19 (18)
C5—C6—C8—O1112.5 (2)C9A—C10A—C11A—C12A0.6 (3)
C7—C6—C8—O1122.8 (2)C10A—C11A—C12A—C13A1.0 (3)
C5—C6—C8—C265.9 (2)C11A—C12A—C13A—C14A0.5 (3)
C7—C6—C8—C258.8 (2)C12A—C13A—C14A—O2A179.41 (18)
N1—C1—C9—C1023.5 (3)C12A—C13A—C14A—C9A0.4 (3)
C2—C1—C9—C1099.1 (2)C10A—C9A—C14A—O2A179.03 (16)
N1—C1—C9—C14160.12 (16)C1A—C9A—C14A—O2A2.4 (2)
C2—C1—C9—C1477.3 (2)C10A—C9A—C14A—C13A0.8 (3)
C14—C9—C10—C110.5 (3)C1A—C9A—C14A—C13A177.77 (16)
C1—C9—C10—C11175.9 (2)N1A—C7A—C17A—C22A37.4 (2)
C9—C10—C11—C120.3 (4)C6A—C7A—C17A—C22A86.8 (2)
C10—C11—C12—C130.4 (4)N1A—C7A—C17A—C18A140.27 (15)
C11—C12—C13—C140.7 (4)C6A—C7A—C17A—C18A95.57 (18)
C12—C13—C14—O2179.9 (2)C22A—C17A—C18A—O3A177.77 (15)
C12—C13—C14—C91.0 (3)C7A—C17A—C18A—O3A4.5 (2)
C10—C9—C14—O2180.0 (2)C22A—C17A—C18A—C19A2.6 (2)
C1—C9—C14—O23.5 (3)C7A—C17A—C18A—C19A175.13 (15)
C10—C9—C14—C130.8 (3)O3A—C18A—C19A—C20A177.73 (17)
C1—C9—C14—C13175.74 (18)C17A—C18A—C19A—C20A2.7 (3)
N1—C7—C17—C2224.0 (2)C18A—C19A—C20A—C21A0.4 (3)
C6—C7—C17—C2299.5 (2)C19A—C20A—C21A—C22A1.9 (3)
N1—C7—C17—C18156.54 (16)C18A—C17A—C22A—C21A0.3 (3)
C6—C7—C17—C1879.9 (2)C7A—C17A—C22A—C21A177.36 (18)
C22—C17—C18—O3179.19 (17)C20A—C21A—C22A—C17A1.9 (3)
C7—C17—C18—O30.3 (2)C9—C1—N1—C7177.56 (15)
C22—C17—C18—C190.8 (3)C2—C1—N1—C759.85 (19)
C7—C17—C18—C19179.73 (17)C17—C7—N1—C1178.51 (14)
O3—C18—C19—C20179.18 (18)C6—C7—N1—C157.74 (19)
C17—C18—C19—C200.8 (3)C9A—C1A—N1A—C7A176.10 (13)
C18—C19—C20—C210.1 (3)C2A—C1A—N1A—C7A60.01 (17)
C19—C20—C21—C220.6 (3)C17A—C7A—N1A—C1A174.44 (13)
C18—C17—C22—C210.1 (3)C6A—C7A—N1A—C1A59.81 (17)
C7—C17—C22—C21179.55 (18)C13—C14—O2—C159.5 (3)
C20—C21—C22—C170.6 (3)C9—C14—O2—C15169.7 (2)
N1A—C1A—C2A—C8A58.99 (18)C16—C15—O2—C14174.7 (2)
C9A—C1A—C2A—C8A176.90 (14)C19—C18—O3—C230.6 (3)
N1A—C1A—C2A—C3A61.64 (18)C17—C18—O3—C23179.40 (17)
C9A—C1A—C2A—C3A62.47 (18)C24—C23—O3—C18171.1 (2)
C8A—C2A—C3A—C4A50.9 (2)C13A—C14A—O2A—C15A6.7 (3)
C1A—C2A—C3A—C4A69.3 (2)C9A—C14A—O2A—C15A173.51 (16)
C2A—C3A—C4A—C5A42.5 (2)C16A—C15A—O2A—C14A176.14 (18)
C3A—C4A—C5A—C6A44.4 (2)C19A—C18A—O3A—C23A4.5 (3)
C4A—C5A—C6A—C8A54.4 (2)C17A—C18A—O3A—C23A175.13 (16)
C4A—C5A—C6A—C7A64.9 (2)C24A—C23A—O3A—C18A178.68 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23A···O1A0.972.423.311 (3)153
C23A—H23C···O10.972.433.297 (3)149

Experimental details

Crystal data
Chemical formulaC24H29NO3
Mr379.49
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)9.7981 (3), 13.6139 (5), 16.7098 (6)
α, β, γ (°)74.363 (2), 80.464 (2), 83.563 (2)
V3)2111.42 (13)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.35 × 0.28 × 0.22
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.973, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
27579, 9839, 6037
Rint0.022
(sin θ/λ)max1)0.673
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.150, 1.02
No. of reflections9839
No. of parameters509
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.53, 0.45

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23A···O1A0.972.423.311 (3)153
C23A—H23C···O10.972.433.297 (3)149
 

Acknowledgements

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

References

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