Crystal structure of 1-[2,4-bis(4-methoxy­phenyl)-3-azabicyclo[3.3.1]nonan-3-yl]ethanone

Shreevidhyaa Suressh, V.; Sathya, S.; Akila, A.; Ponnuswamy, S.; Usha, G.

doi:10.1107/S1600536814022545

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages o1171-o1172

doi:10.1107/S1600536814022545

Open

access

Crystal structure of 1-[2,4-bis(4-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-3-yl]ethanone

V. Shreevidhyaa Suressh,^a S. Sathya,^b A. Akila,^c S. Ponnuswamy ^c and G. Usha ^b ^*

^aDepartment of Physics, Anna Adarsh College for Women, Chennai-40, Tamilnadu, India, ^bPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, and ^cPG and Research Department of Chemistry, Government Arts College, Coimbatore-18, Tamilnadu, India
^*Correspondence e-mail: guqmc@yahoo.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 13 October 2014; accepted 14 October 2014; online 24 October 2014)

In the title compound, C₂₄H₂₉NO₃, the azabicycle contains two six-membered rings, viz. a cyclohexane ring and a piperidine ring. The first adopts a chair conformation and the second a half-chair conformation. The dihedral angle between their mean planes is 86.21 (13)°, indicating that they are almost perpendicular to one another. The dihedral angle between the planes of the 4-methoxyphenyl rings is 17.51 (13)°, and they make dihedral angles of 81.9 (3) and 81.3 (3)° with the ethan-1-one group. In the crystal, molecules are linked by C—H⋯π interactions forming chains along [10-1].

Keywords: crystal structure; azabicyclo[3.3.1]nonane; cyclohexane ring; piperidine ring.

CCDC reference: 1029084

1. Related literature

For the biological activity of piperidine derivatives, see: Barker et al. (2005 ); Hardick et al. (1996 ); Jeyaraman & Avila (1981 ); Parthiban, Aridoss et al. (2009 ); Parthiban, Rathika et al. (2010 ). For the crystal structures of similar compounds, see: Parthiban et al. (2008 ); Parthiban, Ramkumar et al. (2009 , 2010 ).

2. Experimental

2.1. Crystal data

C₂₄H₂₉NO₃
M_r = 379.48
Monoclinic, P 2₁ /n
a = 7.6309 (13) Å
b = 17.102 (3) Å
c = 15.395 (2) Å
β = 93.886 (5)°
V = 2004.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.35 × 0.30 × 0.25 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.972, T_max = 0.980
17249 measured reflections
4597 independent reflections
2524 reflections with I > 2σ(I)
R_int = 0.070

2.3. Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.267
S = 0.86
4597 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C18–C23 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cgⁱ	0.93	2.97	3.843 (3)	158
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1029084

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814022545/su2798sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814022545/su2798Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814022545/su2798Isup3.cml

checkCIF report

Comment top

Azabicyclononanes are present in many alkaloids and they have immense biological activities (Jeyaraman & Avila, 1981; Hardick et al., 1996; Barker et al., 2005). This class of compounds has been observed to exhibit a wide range of biological activities, like antifungal, antibacterial, antimycobacterial, analgesic, antagonistic, anticancer, anti-inflammatory, local anesthetic and hypotensive activity (Parthiban, Aridoss et al., 2009; Parthiban, Rathika et al., 2010).

The molecular structure of the title compound is illustrated in Fig. 1. The cyclohexane ring (C4–C6/C8–C10) adopts a chair conformation [puckering parameters of q2 = 1.3151 (6) Å, T2 = -21.70 (4)°, q3 = 0.0436 (7) Å, QT = 1.3158 (6) Å and ϕ2 = 88.10 (3)° with the smallest asymmetry parameter D2(C5) = 0.0757 (1)°]. The piperidine ring (C3–C7/N1) adopts a half-chair conformation [puckering parameters of q2 = 0.4230 (5) Å, T2 = 133.78 (5)°, q3 = -0.4053 (5) Å, QT = 0.5858 (5) Å and ϕ2 = 0.60 (7)° with the smallest asymmetry parameters DS(N1) = 0.0027 (3)° and D2(N1) = 0.2432 (2)°]. Their mean planes are almost normal to one another with a dihedral angle of 86.21 (13)°. The two benzene rings (C11–C16 and C18–C23) are inclined to one another by 17.51 (13)°.

In the crystal, molecules are linked by C—H···π interactions, forming chains along [101] (Table 1 and Fig. 2).

Related literature top

For the biological activity of piperidine derivatives, see: Barker et al. (2005); Hardick et al. (1996); Jeyaraman & Avila (1981); Parthiban, Aridoss et al. (2009); Parthiban, Rathika et al. (2010). For the crystal structures of similar compounds, see: Parthiban et al. (2008); Parthiban, Ramkumar et al. (2009, 2010).

Experimental top

2,4-Bis(4-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one (5 mmol) was dissolved in benzene (80 ml). To this solution, triethylamine (20 mmol) and acetyl chloride (20 mmol) were added and the reaction mixture was stirred using a magnetic stirrer. The precipitated ammonium salt was dried, purified and evaporated. The oily mass was crystallized from petroleum ether (333–353 K).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

A view of the crystal packing of the title compound, with C—H···π interactions indicted by dashed lines (see Table 1 for details).

1-[2,4-Bis(4-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-3-yl]ethanone top

Crystal data top

C₂₄H₂₉NO₃	F(000) = 816
M_r = 379.48	D_x = 1.258 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4597 reflections
a = 7.6309 (13) Å	θ = 1.8–27.5°
b = 17.102 (3) Å	µ = 0.08 mm⁻¹
c = 15.395 (2) Å	T = 293 K
β = 93.886 (5)°	Block, colourless
V = 2004.5 (6) Å³	0.35 × 0.30 × 0.25 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	4597 independent reflections
Radiation source: fine-focus sealed tube	2524 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
ω and ϕ scan	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
T_min = 0.972, T_max = 0.980	k = −17→22
17249 measured reflections	l = −11→19

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.267	H-atom parameters constrained
S = 0.86	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
4597 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₄H₂₉NO₃	V = 2004.5 (6) Å³
M_r = 379.48	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.6309 (13) Å	µ = 0.08 mm⁻¹
b = 17.102 (3) Å	T = 293 K
c = 15.395 (2) Å	0.35 × 0.30 × 0.25 mm
β = 93.886 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4597 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2524 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.980	R_int = 0.070
17249 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.267	H-atom parameters constrained
S = 0.86	Δρ_max = 0.36 e Å⁻³
4597 reflections	Δρ_min = −0.31 e Å⁻³
253 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
C17	0.8638 (4)	0.0399 (2)	−0.3303 (2)	0.0653 (9)
H17A	0.9081	0.0196	−0.3826	0.098*
H17B	0.8454	−0.0023	−0.2909	0.098*
H17C	0.9472	0.0760	−0.3034	0.098*
O2	0.7019 (3)	0.07911 (13)	−0.35081 (12)	0.0573 (6)
C1	0.5412 (3)	0.29402 (17)	0.00731 (18)	0.0436 (7)
C2	0.6109 (4)	0.32952 (18)	−0.0732 (2)	0.0568 (8)
H2A	0.5557	0.3049	−0.1240	0.085*
H2B	0.7356	0.3217	−0.0721	0.085*
H2C	0.5857	0.3845	−0.0748	0.085*
C3	0.3379 (3)	0.21999 (15)	0.08463 (15)	0.0374 (6)
H3	0.3145	0.2716	0.1091	0.045*
C4	0.1578 (3)	0.17762 (16)	0.07593 (18)	0.0433 (7)
H4	0.0932	0.1932	0.1261	0.052*
C5	0.0536 (3)	0.20673 (18)	−0.00516 (18)	0.0484 (7)
H5A	0.0475	0.2634	−0.0046	0.058*
H5B	−0.0652	0.1863	−0.0071	0.058*
C6	0.1460 (3)	0.17879 (15)	−0.08472 (18)	0.0427 (7)
H6	0.0733	0.1948	−0.1366	0.051*
C7	0.3238 (3)	0.22232 (15)	−0.08655 (16)	0.0367 (6)
H7	0.2947	0.2745	−0.1095	0.044*
C8	0.1669 (4)	0.08798 (17)	0.07604 (19)	0.0515 (8)
H8A	0.2353	0.0706	0.1279	0.062*
H8B	0.0492	0.0670	0.0781	0.062*
C9	0.2488 (4)	0.05627 (17)	−0.00362 (18)	0.0504 (8)
H9A	0.2391	−0.0003	−0.0046	0.061*
H9B	0.3725	0.0697	−0.0009	0.061*
C10	0.1580 (4)	0.08982 (16)	−0.0861 (2)	0.0514 (7)
H10A	0.2217	0.0739	−0.1356	0.062*
H10B	0.0404	0.0683	−0.0939	0.062*
C11	0.4351 (3)	0.18444 (14)	−0.15337 (16)	0.0369 (6)
C12	0.3798 (4)	0.19133 (16)	−0.24134 (17)	0.0445 (7)
H12	0.2807	0.2210	−0.2573	0.053*
C13	0.4695 (4)	0.15478 (18)	−0.30543 (17)	0.0485 (7)
H13	0.4288	0.1591	−0.3636	0.058*
C14	0.6198 (4)	0.11180 (16)	−0.28286 (17)	0.0418 (6)
C15	0.6765 (4)	0.10439 (16)	−0.19611 (17)	0.0453 (7)
H15	0.7769	0.0756	−0.1802	0.054*
C16	0.5828 (3)	0.14024 (16)	−0.13281 (17)	0.0433 (7)
H16	0.6212	0.1341	−0.0746	0.052*
C18	0.4612 (3)	0.17922 (15)	0.15212 (16)	0.0374 (6)
C19	0.4146 (4)	0.17657 (17)	0.23760 (17)	0.0468 (7)
H19	0.3166	0.2046	0.2526	0.056*
C20	0.5081 (4)	0.13399 (18)	0.30143 (17)	0.0490 (7)
H20	0.4711	0.1326	0.3577	0.059*
C21	0.6567 (4)	0.09341 (16)	0.28126 (17)	0.0453 (7)
C22	0.7103 (4)	0.09808 (17)	0.19684 (18)	0.0469 (7)
H22	0.8128	0.0730	0.1828	0.056*
C23	0.6124 (3)	0.13963 (16)	0.13384 (17)	0.0428 (7)
H23	0.6492	0.1410	0.0775	0.051*
C24	0.6961 (5)	0.0322 (2)	0.4205 (2)	0.0767 (11)
H24A	0.7826	0.0026	0.4546	0.115*
H24B	0.5899	0.0022	0.4123	0.115*
H24C	0.6724	0.0800	0.4502	0.115*
N1	0.4169 (3)	0.23550 (12)	−0.00014 (12)	0.0360 (5)
O1	0.5968 (3)	0.31891 (13)	0.07875 (14)	0.0597 (6)
O3	0.7598 (3)	0.04949 (14)	0.33867 (13)	0.0630 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C17	0.070 (2)	0.064 (2)	0.064 (2)	0.0193 (17)	0.0146 (17)	−0.0021 (16)
O2	0.0631 (13)	0.0652 (14)	0.0442 (11)	0.0102 (11)	0.0079 (10)	−0.0055 (10)
C1	0.0374 (15)	0.0421 (15)	0.0515 (17)	−0.0049 (12)	0.0034 (12)	−0.0017 (13)
C2	0.0556 (18)	0.0518 (18)	0.064 (2)	−0.0179 (14)	0.0117 (15)	0.0049 (14)
C3	0.0374 (14)	0.0358 (14)	0.0397 (14)	−0.0005 (11)	0.0086 (11)	−0.0041 (11)
C4	0.0357 (14)	0.0470 (16)	0.0483 (16)	−0.0040 (12)	0.0115 (12)	0.0034 (12)
C5	0.0313 (14)	0.0492 (17)	0.0648 (19)	0.0001 (12)	0.0032 (13)	0.0075 (14)
C6	0.0338 (14)	0.0456 (16)	0.0477 (15)	−0.0032 (12)	−0.0055 (11)	0.0053 (12)
C7	0.0355 (13)	0.0336 (14)	0.0407 (14)	0.0011 (11)	0.0011 (11)	0.0041 (10)
C8	0.0488 (16)	0.0467 (17)	0.0588 (18)	−0.0121 (13)	0.0016 (14)	0.0132 (14)
C9	0.0506 (17)	0.0371 (16)	0.063 (2)	−0.0080 (13)	−0.0009 (14)	0.0040 (13)
C10	0.0493 (17)	0.0435 (17)	0.0601 (18)	−0.0119 (13)	−0.0054 (14)	−0.0028 (14)
C11	0.0377 (14)	0.0348 (14)	0.0378 (13)	−0.0012 (11)	−0.0009 (11)	0.0025 (11)
C12	0.0440 (15)	0.0485 (17)	0.0401 (14)	0.0068 (13)	−0.0048 (12)	0.0055 (12)
C13	0.0553 (17)	0.0549 (18)	0.0345 (14)	0.0035 (14)	−0.0017 (12)	0.0024 (12)
C14	0.0448 (15)	0.0432 (15)	0.0376 (13)	−0.0006 (12)	0.0041 (11)	−0.0011 (11)
C15	0.0422 (15)	0.0488 (17)	0.0445 (15)	0.0091 (13)	−0.0001 (12)	0.0004 (12)
C16	0.0428 (15)	0.0502 (16)	0.0363 (13)	0.0056 (13)	−0.0023 (11)	0.0026 (12)
C18	0.0382 (14)	0.0371 (14)	0.0374 (13)	−0.0039 (11)	0.0063 (11)	−0.0023 (10)
C19	0.0407 (15)	0.0607 (19)	0.0400 (15)	0.0036 (13)	0.0100 (12)	−0.0045 (13)
C20	0.0486 (16)	0.0635 (19)	0.0361 (14)	0.0015 (14)	0.0112 (12)	0.0015 (13)
C21	0.0458 (15)	0.0460 (16)	0.0437 (15)	−0.0018 (13)	−0.0002 (12)	0.0041 (12)
C22	0.0440 (15)	0.0549 (18)	0.0426 (15)	0.0072 (13)	0.0085 (12)	−0.0051 (13)
C23	0.0441 (15)	0.0490 (16)	0.0359 (13)	0.0041 (13)	0.0080 (11)	−0.0029 (12)
C24	0.084 (2)	0.090 (3)	0.056 (2)	0.001 (2)	−0.0027 (18)	0.0272 (19)
N1	0.0338 (11)	0.0365 (12)	0.0376 (11)	−0.0050 (9)	0.0028 (9)	0.0016 (9)
O1	0.0614 (14)	0.0608 (14)	0.0563 (13)	−0.0233 (11)	0.0008 (10)	−0.0103 (10)
O3	0.0631 (14)	0.0753 (16)	0.0499 (12)	0.0115 (12)	−0.0012 (10)	0.0149 (11)

Geometric parameters (Å, º) top

C17—O2	1.423 (4)	C9—C10	1.518 (4)
C17—H17A	0.9600	C9—H9A	0.9700
C17—H17B	0.9600	C9—H9B	0.9700
C17—H17C	0.9600	C10—H10A	0.9700
O2—C14	1.374 (3)	C10—H10B	0.9700
C1—O1	1.228 (3)	C11—C16	1.376 (4)
C1—N1	1.378 (3)	C11—C12	1.396 (3)
C1—C2	1.509 (4)	C12—C13	1.387 (4)
C2—H2A	0.9600	C12—H12	0.9300
C2—H2B	0.9600	C13—C14	1.387 (4)
C2—H2C	0.9600	C13—H13	0.9300
C3—N1	1.498 (3)	C14—C15	1.381 (4)
C3—C18	1.522 (4)	C15—C16	1.390 (4)
C3—C4	1.552 (3)	C15—H15	0.9300
C3—H3	0.9800	C16—H16	0.9300
C4—C5	1.518 (4)	C18—C23	1.383 (4)
C4—C8	1.535 (4)	C18—C19	1.387 (3)
C4—H4	0.9800	C19—C20	1.382 (4)
C5—C6	1.531 (4)	C19—H19	0.9300
C5—H5A	0.9700	C20—C21	1.383 (4)
C5—H5B	0.9700	C20—H20	0.9300
C6—C10	1.524 (4)	C21—O3	1.367 (3)
C6—C7	1.549 (4)	C21—C22	1.391 (4)
C6—H6	0.9800	C22—C23	1.380 (4)
C7—N1	1.482 (3)	C22—H22	0.9300
C7—C11	1.522 (3)	C23—H23	0.9300
C7—H7	0.9800	C24—O3	1.412 (4)
C8—C9	1.514 (4)	C24—H24A	0.9600
C8—H8A	0.9700	C24—H24B	0.9600
C8—H8B	0.9700	C24—H24C	0.9600

O2—C17—H17A	109.5	C8—C9—H9B	109.5
O2—C17—H17B	109.5	C10—C9—H9B	109.5
H17A—C17—H17B	109.5	H9A—C9—H9B	108.1
O2—C17—H17C	109.5	C6—C10—C9	113.0 (2)
H17A—C17—H17C	109.5	C6—C10—H10A	109.0
H17B—C17—H17C	109.5	C9—C10—H10A	109.0
C14—O2—C17	117.2 (2)	C6—C10—H10B	109.0
O1—C1—N1	121.4 (2)	C9—C10—H10B	109.0
O1—C1—C2	118.5 (3)	H10A—C10—H10B	107.8
N1—C1—C2	120.2 (2)	C16—C11—C12	117.3 (2)
C1—C2—H2A	109.5	C16—C11—C7	124.3 (2)
C1—C2—H2B	109.5	C12—C11—C7	118.3 (2)
H2A—C2—H2B	109.5	C13—C12—C11	121.4 (2)
C1—C2—H2C	109.5	C13—C12—H12	119.3
H2A—C2—H2C	109.5	C11—C12—H12	119.3
H2B—C2—H2C	109.5	C12—C13—C14	120.0 (2)
N1—C3—C18	114.16 (19)	C12—C13—H13	120.0
N1—C3—C4	114.5 (2)	C14—C13—H13	120.0
C18—C3—C4	110.3 (2)	O2—C14—C15	124.7 (2)
N1—C3—H3	105.7	O2—C14—C13	115.9 (2)
C18—C3—H3	105.7	C15—C14—C13	119.4 (2)
C4—C3—H3	105.7	C14—C15—C16	119.7 (2)
C5—C4—C8	110.5 (2)	C14—C15—H15	120.2
C5—C4—C3	109.2 (2)	C16—C15—H15	120.2
C8—C4—C3	115.2 (2)	C11—C16—C15	122.2 (2)
C5—C4—H4	107.2	C11—C16—H16	118.9
C8—C4—H4	107.2	C15—C16—H16	118.9
C3—C4—H4	107.2	C23—C18—C19	116.6 (2)
C4—C5—C6	108.2 (2)	C23—C18—C3	124.8 (2)
C4—C5—H5A	110.1	C19—C18—C3	118.5 (2)
C6—C5—H5A	110.1	C20—C19—C18	122.6 (3)
C4—C5—H5B	110.1	C20—C19—H19	118.7
C6—C5—H5B	110.1	C18—C19—H19	118.7
H5A—C5—H5B	108.4	C19—C20—C21	119.8 (2)
C10—C6—C5	110.7 (2)	C19—C20—H20	120.1
C10—C6—C7	115.2 (2)	C21—C20—H20	120.1
C5—C6—C7	108.4 (2)	O3—C21—C22	116.3 (2)
C10—C6—H6	107.4	O3—C21—C20	125.1 (3)
C5—C6—H6	107.4	C22—C21—C20	118.6 (3)
C7—C6—H6	107.4	C23—C22—C21	120.4 (3)
N1—C7—C11	114.6 (2)	C23—C22—H22	119.8
N1—C7—C6	115.1 (2)	C21—C22—H22	119.8
C11—C7—C6	109.7 (2)	C18—C23—C22	121.9 (2)
N1—C7—H7	105.5	C18—C23—H23	119.1
C11—C7—H7	105.5	C22—C23—H23	119.1
C6—C7—H7	105.5	O3—C24—H24A	109.5
C9—C8—C4	112.2 (2)	O3—C24—H24B	109.5
C9—C8—H8A	109.2	H24A—C24—H24B	109.5
C4—C8—H8A	109.2	O3—C24—H24C	109.5
C9—C8—H8B	109.2	H24A—C24—H24C	109.5
C4—C8—H8B	109.2	H24B—C24—H24C	109.5
H8A—C8—H8B	107.9	C1—N1—C7	118.1 (2)
C8—C9—C10	110.6 (3)	C1—N1—C3	111.8 (2)
C8—C9—H9A	109.5	C7—N1—C3	123.93 (19)
C10—C9—H9A	109.5	C21—O3—C24	118.3 (2)

N1—C3—C4—C5	−36.4 (3)	C12—C11—C16—C15	0.9 (4)
C18—C3—C4—C5	−166.8 (2)	C7—C11—C16—C15	177.6 (2)
N1—C3—C4—C8	88.6 (3)	C14—C15—C16—C11	−1.0 (4)
C18—C3—C4—C8	−41.8 (3)	N1—C3—C18—C23	−17.5 (4)
C8—C4—C5—C6	−60.1 (3)	C4—C3—C18—C23	113.1 (3)
C3—C4—C5—C6	67.6 (3)	N1—C3—C18—C19	167.0 (2)
C4—C5—C6—C10	59.2 (3)	C4—C3—C18—C19	−62.4 (3)
C4—C5—C6—C7	−68.1 (3)	C23—C18—C19—C20	−2.9 (4)
C10—C6—C7—N1	−87.1 (3)	C3—C18—C19—C20	173.0 (3)
C5—C6—C7—N1	37.6 (3)	C18—C19—C20—C21	1.6 (5)
C10—C6—C7—C11	43.8 (3)	C19—C20—C21—O3	179.9 (3)
C5—C6—C7—C11	168.5 (2)	C19—C20—C21—C22	1.3 (4)
C5—C4—C8—C9	58.0 (3)	O3—C21—C22—C23	178.5 (2)
C3—C4—C8—C9	−66.3 (3)	C20—C21—C22—C23	−2.8 (4)
C4—C8—C9—C10	−52.3 (3)	C19—C18—C23—C22	1.4 (4)
C5—C6—C10—C9	−56.1 (3)	C3—C18—C23—C22	−174.2 (2)
C7—C6—C10—C9	67.4 (3)	C21—C22—C23—C18	1.4 (4)
C8—C9—C10—C6	51.7 (3)	O1—C1—N1—C7	164.8 (2)
N1—C7—C11—C16	22.7 (3)	C2—C1—N1—C7	−14.6 (4)
C6—C7—C11—C16	−108.5 (3)	O1—C1—N1—C3	11.4 (4)
N1—C7—C11—C12	−160.7 (2)	C2—C1—N1—C3	−168.1 (2)
C6—C7—C11—C12	68.1 (3)	C11—C7—N1—C1	72.4 (3)
C16—C11—C12—C13	0.3 (4)	C6—C7—N1—C1	−159.1 (2)
C7—C11—C12—C13	−176.5 (2)	C11—C7—N1—C3	−137.6 (2)
C11—C12—C13—C14	−1.5 (4)	C6—C7—N1—C3	−9.1 (3)
C17—O2—C14—C15	−5.0 (4)	C18—C3—N1—C1	−71.7 (3)
C17—O2—C14—C13	175.2 (3)	C4—C3—N1—C1	159.8 (2)
C12—C13—C14—O2	−178.7 (2)	C18—C3—N1—C7	136.7 (2)
C12—C13—C14—C15	1.5 (4)	C4—C3—N1—C7	8.2 (3)
O2—C14—C15—C16	179.9 (3)	C22—C21—O3—C24	−169.6 (3)
C13—C14—C15—C16	−0.2 (4)	C20—C21—O3—C24	11.8 (4)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C18–C23 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cgⁱ	0.93	2.97	3.843 (3)	158

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C18–C23 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cgⁱ	0.93	2.97	3.843 (3)	158

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.

Acknowledgements

The authors thank Professor D. Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data-collection facilities.

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 (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Hardick, D. J., Blagbrough, I. S., Cooper, G., Potter, B. V. L., Critchley, T. & Wonnacott, S. (1996). J. Med. Chem. 39, 4860–4866. CrossRef CAS PubMed Web of Science Google Scholar
Jeyaraman, R. & Avila, S. (1981). Chem. Rev. 81, 149–174. CrossRef CAS Web of Science Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Parthiban, P., Aridoss, G., Rathika, P., Ramkumar, V. & Kabilan, S. (2009). 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. (2009). Acta Cryst. E65, o1356. Web of Science CSD CrossRef IUCr Journals Google Scholar
Parthiban, P., Ramkumar, V. & Jeong, Y. T. (2010). Acta Cryst. E66, o48–o49. Web of Science CSD CrossRef IUCr Journals Google Scholar
Parthiban, P., Ramkumar, V., Kim, M. S., Lim, K. T. & Jeong, Y. T. (2008). Acta Cryst. E64, o1586. Web of Science CSD CrossRef IUCr Journals Google Scholar
Parthiban, P., Rathika, P., Park, K. S. & Jeong, Y. T. (2010). Monatsh. Chem. 141, 79–93. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages o1171-o1172

doi:10.1107/S1600536814022545

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Crystal structure of 1-[2,4-bis­(4-meth­oxy­phenyl)-3-azabi­cyclo[3.3.1]nonan-3-yl]ethanone

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 1-[2,4-bis(4-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-3-yl]ethanone