2,4-Bis(furan-2-yl)-1,5-dimethyl-3-aza­bicyclo­[3.3.1]nonan-9-one

Venkateswaramoorthi, R.; Rizwana Begum, S.; Hema, R.; Krishnasamy, K.; Anitha, A.G.

doi:10.1107/S1600536813010180

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o768

https://doi.org/10.1107/S1600536813010180

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2,4-Bis(furan-2-yl)-1,5-dimethyl-3-azabicyclo[3.3.1]nonan-9-one

R. Venkateswaramoorthi,^a S. Rizwana Begum,^b R. Hema,^b ^* K. Krishnasamy ^a and A.G. Anitha ^b

^aDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, India, and ^bDepartment of Physics, Seethalakshmi Ramaswami College (Autonomous), Tiruchirappalli 620 002, India
^*Correspondence e-mail: raghema2000@yahoo.co.in

(Received 12 January 2013; accepted 14 April 2013; online 20 April 2013)

In the title compound, C₁₈H₂₁NO₃, the bicyclic ring system adopts a twin-chair conformation. The two methyl groups attached to the bicycle are in an equatorial orientation for both rings. One of the furan rings is disordered over two orientations with an occupancy ratio of 0.686 (6):0.314 (6). In the crystal, very long N—H⋯O hydrogen bonds connect the molecules into a chain perpendicular to the ac plane.

Related literature

For the synthesis and biological activity of 3-azabicyclo[3.3.1] nonan-9-ones, see: Parthiban et al. (2009 ); Hardick et al. (1996 ); Jeyaraman & Avila (1981 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₈H₂₁NO₃
M_r = 299.36
Monoclinic, C 2/c
a = 21.268 (2) Å
b = 6.7031 (9) Å
c = 22.303 (2) Å
β = 92.776 (6)°
V = 3175.7 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
11487 measured reflections
2784 independent reflections
2127 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.130
S = 1.05
2784 reflections
252 parameters
220 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.89 (2)	2.84 (2)	3.647 (2)	152.0 (13)
Symmetry code: (i) x, y+1, z.

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 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813010180/aa2083sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813010180/aa2083Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813010180/aa2083Isup3.cml

checkCIF report

Comment top

Molecules with the 3-azabicyclo[3.3.1]nonane nucleus are of great interest due to their presence in a wide variety of naturally occurring diterpenoid/norditerpenoid alkaloids and their broad-spectrum biological activities such as antimicrobial, analgesic, antogonistic, anti-inflammatory, local anesthetic hypotensive activity and so on (Parthiban et al., 2009; Hardick et al., 1996; Jeyaraman & Avila, 1981). Hence, the synthesis of new molecules with the 3-azabicyclo[3.3.1] nonane nucleus and their stereochemical investigations are of interest in the field of medicinal chemistry. Also, the stereochemistry of the synthesized molecules is a major criterium for their biological response. Hence, it is important to establish the stereochemistry of the bio-active molecules. As a consequence, the present study was undertaken to examine the configuration and conformation of the synthesized title compound.

In the crystal structure of the title compound, the bicycle system adopts twin-chair conformation with puckering parameters Q = 0.571 (2) Å, θ = 178.3 (2)° and φ = 360 (5)° for the piperidine ring N1/C2/C3/C8/C7/C9 and Q = 0.568 (2) Å, θ = 168.0 (2)° and φ = 121.4 (10)° for the cyclohexanone ring C3/C4/C5/C6/C7/C8 (Cremer & Pople, 1975).

The dihedral angle between the furyl ring C21/C22/C23/C24/O2 and the piperidine ring N1/C2/C3/C8/C7/C9 is 70.09 (8)° and the disordered furyl ring makes with the same piperidine ring two dihedral angles of 70.83 (23)° for major part C91/C92/C93/C94/O3 and 67.40 (36)° for minor part C91/C92'/C93'/C94'/O3'. The methyl groups attached at C7 and C3 are in equitorial orientation with torsion angles of 175.31 (19)° (N1–C9–C7–C11) and -174.72 (17)° (N1–C2–C3–C10).

Related literature top

For the synthesis and biological activity of 3-azabicyclo[3.3.1] nonan-9-ones, see: Parthiban et al. (2009); Hardick et al. (1996); Jeyaraman & Avila (1981). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

The title compound was obtained by condensation of 2,6-dimethylcyclohexanone, furfuraldehyde and ammonium acetate in 1:2:1 ratio in ethanol. The reaction mixture was warmed and stirred until the completion of reaction. The crude product was washed with an ethanol - ethyl ether (1:5) mixture and recrystallized from ethanol - chloroform (1:1) to obtain the pure compound.

Structure description top

For the synthesis and biological activity of 3-azabicyclo[3.3.1] nonan-9-ones, see: Parthiban et al. (2009); Hardick et al. (1996); Jeyaraman & Avila (1981). For puckering parameters, see: Cremer & Pople (1975).

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); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. View of the molecule of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by circles of arbitrary radii.

2,4-Bis(furan-2-yl)-1,5-dimethyl-3-azabicyclo[3.3.1]nonan-9-one top

Crystal data top

C₁₈H₂₁NO₃	F(000) = 1280
M_r = 299.36	D_x = 1.252 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 11487 reflections
a = 21.268 (2) Å	θ = 1.8–28.4°
b = 6.7031 (9) Å	µ = 0.09 mm⁻¹
c = 22.303 (2) Å	T = 293 K
β = 92.776 (6)°	Block, brown
V = 3175.7 (6) Å³	0.30 × 0.25 × 0.20 mm
Z = 8

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2127 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 25.0°, θ_min = 1.9°
ω scan	h = −23→25
11487 measured reflections	k = −5→7
2784 independent reflections	l = −22→26

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.130	w = 1/[σ²(F_o²) + (0.0637P)² + 1.7182P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2784 reflections	Δρ_max = 0.19 e Å⁻³
252 parameters	Δρ_min = −0.20 e Å⁻³
220 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0024 (5)

Crystal data top

C₁₈H₂₁NO₃	V = 3175.7 (6) Å³
M_r = 299.36	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 21.268 (2) Å	µ = 0.09 mm⁻¹
b = 6.7031 (9) Å	T = 293 K
c = 22.303 (2) Å	0.30 × 0.25 × 0.20 mm
β = 92.776 (6)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2127 reflections with I > 2σ(I)
11487 measured reflections	R_int = 0.031
2784 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	220 restraints
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.19 e Å⁻³
2784 reflections	Δρ_min = −0.20 e Å⁻³
252 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	Occ. (<1)
N1	0.17290 (7)	0.0845 (3)	0.13064 (7)	0.0446 (4)
H1	0.1765 (10)	0.215 (4)	0.1368 (9)	0.058 (6)*
C2	0.23315 (8)	−0.0076 (3)	0.15048 (8)	0.0391 (4)
H2	0.2398	0.0198	0.1935	0.047*
C3	0.23109 (8)	−0.2391 (3)	0.14260 (8)	0.0403 (4)
C4	0.21984 (10)	−0.3083 (3)	0.07672 (8)	0.0506 (5)
H4A	0.2530	−0.2539	0.0532	0.061*
H4B	0.2233	−0.4526	0.0755	0.061*
C5	0.15671 (10)	−0.2485 (3)	0.04728 (9)	0.0562 (6)
H5A	0.1501	−0.3209	0.0098	0.067*
H5B	0.1573	−0.1072	0.0380	0.067*
C6	0.10205 (10)	−0.2917 (3)	0.08770 (9)	0.0544 (5)
H6A	0.0942	−0.4342	0.0873	0.065*
H6B	0.0646	−0.2267	0.0706	0.065*
C7	0.11233 (9)	−0.2234 (3)	0.15358 (8)	0.0455 (5)
C8	0.17479 (9)	−0.3139 (3)	0.17506 (8)	0.0444 (5)
C9	0.11855 (8)	0.0068 (3)	0.16110 (9)	0.0461 (5)
H9	0.1259	0.0337	0.2041	0.055*
C10	0.29224 (10)	−0.3283 (3)	0.16918 (10)	0.0595 (6)
H10A	0.3007	−0.2761	0.2088	0.089*
H10B	0.3262	−0.2941	0.1443	0.089*
H10C	0.2883	−0.4708	0.1711	0.089*
C11	0.05852 (10)	−0.2986 (4)	0.19039 (11)	0.0701 (7)
H11A	0.0591	−0.4417	0.1914	0.105*
H11B	0.0191	−0.2537	0.1724	0.105*
H11C	0.0635	−0.2476	0.2306	0.105*
C21	0.28552 (8)	0.0899 (3)	0.11924 (8)	0.0418 (4)
C22	0.34330 (9)	0.1509 (3)	0.13830 (10)	0.0559 (5)
H22	0.3611	0.1405	0.1771	0.067*
C23	0.37202 (10)	0.2347 (3)	0.08755 (11)	0.0627 (6)
H23	0.4122	0.2893	0.0869	0.075*
C24	0.33033 (10)	0.2198 (3)	0.04147 (11)	0.0616 (6)
H24	0.3368	0.2637	0.0027	0.074*
O1	0.17859 (7)	−0.4444 (3)	0.21255 (7)	0.0744 (5)
O2	0.27645 (6)	0.1308 (2)	0.05925 (6)	0.0564 (4)
C91	0.0595 (4)	0.114 (2)	0.1410 (2)	0.0532 (11)	0.686 (6)
C92	0.0368 (2)	0.1727 (7)	0.0867 (2)	0.0656 (11)	0.686 (6)
H92	0.0561	0.1616	0.0503	0.079*	0.686 (6)
C93	−0.0247 (4)	0.2576 (19)	0.0973 (3)	0.0883 (17)	0.686 (6)
H93	−0.0535	0.3089	0.0686	0.106*	0.686 (6)
C94	−0.03169 (18)	0.2467 (7)	0.1581 (3)	0.0947 (15)	0.686 (6)
H94	−0.0667	0.2934	0.1772	0.114*	0.686 (6)
O3	0.02057 (15)	0.1562 (6)	0.18791 (19)	0.0811 (11)	0.686 (6)
C91'	0.0638 (9)	0.116 (5)	0.1303 (6)	0.064 (2)	0.314 (6)
C92'	0.0621 (4)	0.1568 (14)	0.0708 (4)	0.0480 (18)	0.314 (6)
H92'	0.0929	0.1318	0.0436	0.058*	0.314 (6)
C93'	0.0022 (4)	0.2467 (14)	0.0597 (5)	0.082 (2)	0.314 (6)
H93'	−0.0137	0.2875	0.0221	0.098*	0.314 (6)
C94'	−0.0289 (9)	0.265 (4)	0.1116 (7)	0.082 (2)	0.314 (6)
H94'	−0.0680	0.3245	0.1158	0.099*	0.314 (6)
O3'	0.0093 (4)	0.1787 (15)	0.1571 (5)	0.094 (2)	0.314 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0369 (8)	0.0346 (9)	0.0622 (10)	0.0025 (7)	0.0027 (7)	0.0001 (7)
C2	0.0388 (9)	0.0386 (10)	0.0398 (9)	0.0028 (8)	0.0001 (7)	−0.0037 (8)
C3	0.0432 (10)	0.0366 (10)	0.0414 (10)	0.0047 (8)	0.0041 (8)	0.0007 (8)
C4	0.0621 (12)	0.0438 (11)	0.0471 (11)	−0.0023 (9)	0.0137 (9)	−0.0073 (9)
C5	0.0743 (14)	0.0538 (13)	0.0401 (10)	−0.0032 (11)	−0.0026 (10)	−0.0072 (9)
C6	0.0555 (12)	0.0462 (12)	0.0607 (13)	−0.0067 (9)	−0.0071 (10)	−0.0054 (9)
C7	0.0431 (10)	0.0451 (11)	0.0486 (11)	−0.0034 (8)	0.0069 (8)	0.0035 (8)
C8	0.0551 (11)	0.0418 (11)	0.0365 (9)	0.0000 (8)	0.0039 (8)	0.0026 (8)
C9	0.0386 (10)	0.0501 (12)	0.0499 (11)	−0.0001 (9)	0.0054 (8)	−0.0064 (9)
C10	0.0556 (12)	0.0497 (12)	0.0733 (14)	0.0126 (10)	0.0026 (10)	0.0093 (11)
C11	0.0558 (13)	0.0720 (16)	0.0838 (16)	−0.0081 (11)	0.0176 (12)	0.0169 (13)
C21	0.0400 (10)	0.0379 (10)	0.0473 (10)	0.0038 (8)	0.0005 (8)	−0.0019 (8)
C22	0.0410 (11)	0.0607 (14)	0.0654 (13)	−0.0006 (9)	−0.0031 (9)	−0.0045 (11)
C23	0.0416 (11)	0.0576 (14)	0.0899 (17)	−0.0072 (10)	0.0141 (11)	0.0002 (12)
C24	0.0550 (13)	0.0567 (14)	0.0746 (15)	−0.0069 (10)	0.0171 (11)	0.0122 (11)
O1	0.0700 (10)	0.0808 (12)	0.0729 (10)	0.0022 (8)	0.0074 (8)	0.0381 (9)
O2	0.0516 (8)	0.0614 (10)	0.0559 (9)	−0.0083 (7)	0.0004 (6)	0.0124 (7)
C91	0.029 (2)	0.045 (2)	0.086 (3)	0.0037 (18)	0.0108 (19)	−0.010 (3)
C92	0.038 (2)	0.058 (2)	0.098 (3)	0.010 (2)	−0.018 (2)	0.007 (2)
C93	0.049 (3)	0.076 (3)	0.138 (4)	0.009 (2)	−0.016 (3)	−0.005 (4)
C94	0.0333 (18)	0.089 (3)	0.162 (4)	0.0174 (18)	0.000 (2)	−0.018 (3)
O3	0.0495 (16)	0.090 (2)	0.105 (3)	0.0131 (13)	0.0101 (16)	−0.013 (2)
C91'	0.042 (4)	0.058 (4)	0.092 (4)	−0.003 (4)	0.017 (4)	−0.014 (4)
C92'	0.025 (3)	0.054 (3)	0.064 (4)	0.016 (3)	−0.003 (3)	0.004 (3)
C93'	0.057 (4)	0.073 (4)	0.114 (5)	0.004 (4)	−0.021 (4)	0.000 (4)
C94'	0.043 (4)	0.072 (4)	0.130 (5)	0.014 (4)	−0.009 (4)	−0.002 (5)
O3'	0.066 (4)	0.084 (3)	0.133 (4)	0.008 (3)	0.009 (4)	−0.007 (4)

Geometric parameters (Å, º) top

N1—C9	1.464 (2)	C11—H11A	0.9600
N1—C2	1.471 (2)	C11—H11B	0.9600
N1—H1	0.89 (2)	C11—H11C	0.9600
C2—C21	1.493 (2)	C21—C22	1.344 (3)
C2—C3	1.562 (3)	C21—O2	1.370 (2)
C2—H2	0.9800	C22—C23	1.427 (3)
C3—C8	1.514 (3)	C22—H22	0.9300
C3—C10	1.525 (3)	C23—C24	1.328 (3)
C3—C4	1.548 (3)	C23—H23	0.9300
C4—C5	1.520 (3)	C24—O2	1.368 (2)
C4—H4A	0.9700	C24—H24	0.9300
C4—H4B	0.9700	C91—C92	1.342 (5)
C5—C6	1.533 (3)	C91—O3	1.393 (4)
C5—H5A	0.9700	C92—C93	1.455 (7)
C5—H5B	0.9700	C92—H92	0.9300
C6—C7	1.544 (3)	C93—C94	1.373 (7)
C6—H6A	0.9700	C93—H93	0.9300
C6—H6B	0.9700	C94—O3	1.405 (5)
C7—C8	1.517 (3)	C94—H94	0.9300
C7—C11	1.526 (3)	C91'—C92'	1.353 (8)
C7—C9	1.557 (3)	C91'—O3'	1.395 (8)
C8—O1	1.210 (2)	C92'—C93'	1.421 (7)
C9—C91	1.497 (4)	C92'—H92'	0.9300
C9—C91'	1.512 (8)	C93'—C94'	1.366 (10)
C9—H9	0.9800	C93'—H93'	0.9300
C10—H10A	0.9600	C94'—O3'	1.396 (9)
C10—H10B	0.9600	C94'—H94'	0.9300
C10—H10C	0.9600

C9—N1—C2	114.00 (15)	C3—C10—H10A	109.5
C9—N1—H1	110.0 (13)	C3—C10—H10B	109.5
C2—N1—H1	107.4 (14)	H10A—C10—H10B	109.5
N1—C2—C21	109.54 (15)	C3—C10—H10C	109.5
N1—C2—C3	111.35 (14)	H10A—C10—H10C	109.5
C21—C2—C3	113.59 (14)	H10B—C10—H10C	109.5
N1—C2—H2	107.4	C7—C11—H11A	109.5
C21—C2—H2	107.4	C7—C11—H11B	109.5
C3—C2—H2	107.4	H11A—C11—H11B	109.5
C8—C3—C10	111.32 (16)	C7—C11—H11C	109.5
C8—C3—C4	105.37 (15)	H11A—C11—H11C	109.5
C10—C3—C4	109.95 (16)	H11B—C11—H11C	109.5
C8—C3—C2	107.08 (14)	C22—C21—O2	109.35 (17)
C10—C3—C2	109.08 (15)	C22—C21—C2	132.61 (18)
C4—C3—C2	113.99 (15)	O2—C21—C2	118.04 (15)
C5—C4—C3	115.06 (16)	C21—C22—C23	106.79 (19)
C5—C4—H4A	108.5	C21—C22—H22	126.6
C3—C4—H4A	108.5	C23—C22—H22	126.6
C5—C4—H4B	108.5	C24—C23—C22	106.79 (18)
C3—C4—H4B	108.5	C24—C23—H23	126.6
H4A—C4—H4B	107.5	C22—C23—H23	126.6
C4—C5—C6	112.07 (17)	C23—C24—O2	110.22 (19)
C4—C5—H5A	109.2	C23—C24—H24	124.9
C6—C5—H5A	109.2	O2—C24—H24	124.9
C4—C5—H5B	109.2	C24—O2—C21	106.86 (16)
C6—C5—H5B	109.2	C92—C91—O3	114.7 (3)
H5A—C5—H5B	107.9	C92—C91—C9	132.1 (4)
C5—C6—C7	115.29 (16)	O3—C91—C9	113.2 (3)
C5—C6—H6A	108.5	C91—C92—C93	104.8 (4)
C7—C6—H6A	108.5	C91—C92—H92	127.6
C5—C6—H6B	108.5	C93—C92—H92	127.6
C7—C6—H6B	108.5	C94—C93—C92	106.3 (5)
H6A—C6—H6B	107.5	C94—C93—H93	126.9
C8—C7—C11	111.48 (16)	C92—C93—H93	126.9
C8—C7—C6	105.26 (15)	C93—C94—O3	111.7 (5)
C11—C7—C6	109.79 (17)	C93—C94—H94	124.2
C8—C7—C9	107.09 (15)	O3—C94—H94	124.2
C11—C7—C9	109.36 (17)	C91—O3—C94	102.6 (4)
C6—C7—C9	113.80 (16)	C92'—C91'—O3'	112.1 (7)
O1—C8—C3	122.80 (18)	C92'—C91'—C9	121.8 (8)
O1—C8—C7	122.38 (17)	O3'—C91'—C9	126.1 (8)
C3—C8—C7	114.66 (15)	C91'—C92'—C93'	103.8 (7)
N1—C9—C91	111.1 (4)	C91'—C92'—H92'	128.1
N1—C9—C91'	103.0 (10)	C93'—C92'—H92'	128.1
N1—C9—C7	111.54 (15)	C94'—C93'—C92'	111.0 (10)
C91—C9—C7	112.2 (6)	C94'—C93'—H93'	124.5
C91'—C9—C7	111.8 (15)	C92'—C93'—H93'	124.5
N1—C9—H9	107.2	C93'—C94'—O3'	106.8 (11)
C91—C9—H9	107.2	C93'—C94'—H94'	126.6
C91'—C9—H9	116.0	O3'—C94'—H94'	126.6
C7—C9—H9	107.2	C91'—O3'—C94'	106.3 (9)

C9—N1—C2—C21	−176.84 (14)	C6—C7—C9—C91'	53.2 (5)
C9—N1—C2—C3	56.7 (2)	N1—C2—C21—C22	137.4 (2)
N1—C2—C3—C8	−54.15 (19)	C3—C2—C21—C22	−97.4 (2)
C21—C2—C3—C8	−178.38 (14)	N1—C2—C21—O2	−42.4 (2)
N1—C2—C3—C10	−174.73 (15)	C3—C2—C21—O2	82.80 (19)
C21—C2—C3—C10	61.0 (2)	O2—C21—C22—C23	0.1 (2)
N1—C2—C3—C4	62.0 (2)	C2—C21—C22—C23	−179.75 (19)
C21—C2—C3—C4	−62.3 (2)	C21—C22—C23—C24	0.1 (3)
C8—C3—C4—C5	53.4 (2)	C22—C23—C24—O2	−0.2 (3)
C10—C3—C4—C5	173.44 (17)	C23—C24—O2—C21	0.3 (2)
C2—C3—C4—C5	−63.7 (2)	C22—C21—O2—C24	−0.2 (2)
C3—C4—C5—C6	−46.9 (2)	C2—C21—O2—C24	179.64 (16)
C4—C5—C6—C7	46.7 (2)	N1—C9—C91—C92	42.8 (16)
C5—C6—C7—C8	−52.7 (2)	C91'—C9—C91—C92	7 (11)
C5—C6—C7—C11	−172.77 (18)	C7—C9—C91—C92	−82.9 (14)
C5—C6—C7—C9	64.3 (2)	N1—C9—C91—O3	−138.8 (8)
C10—C3—C8—O1	−7.6 (3)	C91'—C9—C91—O3	−175 (13)
C4—C3—C8—O1	111.5 (2)	C7—C9—C91—O3	95.6 (10)
C2—C3—C8—O1	−126.8 (2)	O3—C91—C92—C93	−2.0 (13)
C10—C3—C8—C7	176.76 (16)	C9—C91—C92—C93	176.5 (14)
C4—C3—C8—C7	−64.1 (2)	C91—C92—C93—C94	1.9 (11)
C2—C3—C8—C7	57.6 (2)	C92—C93—C94—O3	−1.3 (10)
C11—C7—C8—O1	7.1 (3)	C92—C91—O3—C94	1.2 (12)
C6—C7—C8—O1	−111.9 (2)	C9—C91—O3—C94	−177.5 (8)
C9—C7—C8—O1	126.7 (2)	C93—C94—O3—C91	0.2 (10)
C11—C7—C8—C3	−177.27 (17)	N1—C9—C91'—C92'	37 (3)
C6—C7—C8—C3	63.8 (2)	C91—C9—C91'—C92'	−177 (15)
C9—C7—C8—C3	−57.7 (2)	C7—C9—C91'—C92'	−83 (3)
C2—N1—C9—C91	177.1 (5)	N1—C9—C91'—O3'	−146 (3)
C2—N1—C9—C91'	−176.8 (13)	C91—C9—C91'—O3'	0 (9)
C2—N1—C9—C7	−56.8 (2)	C7—C9—C91'—O3'	95 (3)
C8—C7—C9—N1	54.4 (2)	O3'—C91'—C92'—C93'	−1 (3)
C11—C7—C9—N1	175.29 (16)	C9—C91'—C92'—C93'	176 (3)
C6—C7—C9—N1	−61.5 (2)	C91'—C92'—C93'—C94'	3 (2)
C8—C7—C9—C91	179.8 (2)	C92'—C93'—C94'—O3'	−3 (3)
C11—C7—C9—C91	−59.3 (3)	C92'—C91'—O3'—C94'	0 (3)
C6—C7—C9—C91	63.9 (3)	C9—C91'—O3'—C94'	−178 (3)
C8—C7—C9—C91'	169.1 (5)	C93'—C94'—O3'—C91'	2 (3)
C11—C7—C9—C91'	−70.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.89 (2)	2.84 (2)	3.647 (2)	152.0 (13)

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₁NO₃
M_r	299.36
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	21.268 (2), 6.7031 (9), 22.303 (2)
β (°)	92.776 (6)
V (Å³)	3175.7 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11487, 2784, 2127
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.130, 1.05
No. of reflections	2784
No. of parameters	252
No. of restraints	220
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.89 (2)	2.84 (2)	3.647 (2)	152.0 (13)

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

References

Bruker (2008). APEX2 and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA. 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. (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
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
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

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Volume 69| Part 5| May 2013| Page o768

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