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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o48–o49.
Published online 2009 December 4. doi:  10.1107/S1600536809050697
PMCID: PMC2980113

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

Abstract

In the crystal structure, the title compound, C22H25NO3, exists in a twin-chair conformation with equatorial orientations of the meta-methoxy­phenyl groups on both sides of the secondary amino group. The title compound is a positional isomer of 2,4-bis­(2-methoxy­phen­yl)-3-aza­bicyclo­[3.3.1]nonan-9-one and 2,4-bis­(4-methoxy­phen­yl)-3-aza­bicyclo­[3.3.1]nonan-9-one, which both also exhibit twin-chair conformations with equatorial dispositions of the anisyl rings on both sides of the secondary amino group. In the title compound, the meta-methoxy­phenyl rings are orientated at an angle of 25.02 (3)° with respect to each other, whereas in the ortho and para isomers, the anisyl rings are orientated at dihedral angles of 33.86 (3) and 37.43 (4)°, respectively. The crystal packing is dominated by van der Waals inter­actions and by an inter­molecular N—H(...)O hydrogen bond, whereas in the ortho isomer, an inter­molecular N—H(...)π inter­action (H(...)Cg = 2.75 Å) is found.

Related literature

For the synthesis and biological activity of 3-aza­bicyclo­[3.3.1]nonan-9-ones, see: Jeyaraman & Avila (1981 [triangle]). For the nicotinic acetyl­choline receptor antogonistic activity of diter­penoid/norditerpenoid alkaloids, see: Hardick et al. (1996 [triangle]); Barker et al. (2005 [triangle]). For the structures of the ortho and para OMe-substitued isomers, see: Parthiban et al. (2009a [triangle]); Cox et al. (1985 [triangle]). For related structures, see: Parthiban et al. (2008a [triangle],b [triangle],c [triangle], 2009b [triangle],c [triangle]), Smith-Verdier et al. (1983 [triangle]); Padegimas & Kovacic (1972 [triangle]). For ring puckering analysis, see: Cremer & Pople (1975 [triangle]); Nardelli (1983 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-00o48-scheme1.jpg

Experimental

Crystal data

  • C22H25NO3
  • M r = 351.43
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-00o48-efi1.jpg
  • a = 22.3843 (9) Å
  • b = 6.5666 (3) Å
  • c = 13.0745 (4) Å
  • β = 106.382 (2)°
  • V = 1843.78 (13) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 298 K
  • 0.40 × 0.28 × 0.15 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1999 [triangle]) T min = 0.967, T max = 0.988
  • 12835 measured reflections
  • 3971 independent reflections
  • 2326 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.136
  • S = 1.06
  • 3971 reflections
  • 241 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004 [triangle]); data reduction: SAINT-Plus and XPREP (Bruker, 2004 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050697/zl2238sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050697/zl2238Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

3-Azabicyclo[3.3.1]nonanes are an important class of heterocyclic compounds due to their broad-spectrum of biological activities such as analgesic, antogonistic, anti-inflammatory, local anesthetic and hypotensive activity (Jeyaraman & Avila, 1981). The 3-azabicyclo[3.3.1]nonane pharmacophore is present in numerous naturally occuring diterpenoid/norditerpenoid alkaloids such as methyllycaconitine, elatine, nudicauline, delsoline, delcorine and so on, they act as potential nicotinic acetylcholine receptor antagonists (Hardick et al. 1996; Barker et al. 2005). However, the biological activity mainly depends on the stereochemistry of the molecule; hence, it is of immense help to establish the structures of the synthesized molecules. For the synthesized title compound, several stereoisomers are possible with conformations such as chair-chair (Parthiban et al., 2008a, 2008b, 2008c, 2009a, 2009b, 2009c), chair-boat (Smith-Verdier et al., 1983) and boat-boat (Padegimas & Kovacic, 1972). Hence, the present crystal study was undertaken to explore the configuration and conformation of the synthesized title compound.

The crystallographic analysis of the title compound shows that the piperidine ring adopts a near ideal chair conformation. The total puckering amplitude, QT, is 0.600 (2) Å and the phase angle, θ, is 174.96 (19)° (Cremer & Pople, 1975). The smallest displacement asymmetry parameters being q2 and q3 are 0.053 (2) and -0.598 (2) Å (Nardelli, 1983). The deviation of ring atoms C8 and N1 from the C1/C2/C6/C7 plane are 0.712 (3) and -0.629 (3) Å, respectively.

According to the crystallographic analysis, the cyclohexane ring slightly deviates from the ideal chair conformation. The total puckering amplitude, QT = 0.559 (2) Å and phase angle θ = 166.6 (2)° (Cremer & Pople, 1975). The smallest displacement asymmetry parameters being q2 = 0.130 (2) and q3 = -0.544 (2)Å (Nardelli, 1983). The deviation of ring atoms C4 and C8 from the C2/C3/C5/C6 plane are -0.537 (4) and 0.718 (3) Å, respectively.

Hence the title compound, C22H25NO3, exists in a chair-chair conformation with equatorial orientation of the meta-methoxyphenyl groups on both sides of the secondary amino group on the heterocycle. The title compound is a positional isomer of 2,4-bis(2-methoxyphenyl)-3- azabicyclo[3.3.1]nonan-9-one (Parthiban et al., 2009a) and 2,4-bis (4-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one (Cox et al., 1985). Similar to the title compound the ortho as well as the para isomers also exhibit twin-chair conformations with equatorial disposition of the anisyl rings on both sides of the secondary amino group. In the title compound, the meta-methoxyphenyl rings are orientated at an angle of 25.02 (3)° with respect to one another whereas in the ortho and para isomer, the phenyl rings are orientated at an angle of 33.86 (3)° and 37.43 (4)° respectively.

The torsion angles of C8-C2-C1-C9 and C8-C6-C7-C15 are 179.64 (4) and 178.66 (3)°, respectively, for the title compound, which is very similar to those of its ortho isomer (-179.66 (3) and -179.76 (4)°, respectively) and those for the para isomer (178.2 (2) and 177.9 (4)°, respectively).

The crystal packing is dominated by shape recognition, by van der Waals interactions and is stabilized by an intermolecular N-H···O hydrogen bond (Table 1). In the ortho isomer, on the other hand, the crystal structure exhibits an intermolecular N-H···π interaction (N1-H1A···Cg1 = 2.75 Å).

Experimental

The title compound was synthesized by a modified Mannich reaction using 0.1 mol (13.61 g/12.18 ml) meta-methoxybenzaldehyde, 0.05 mol (4.90 g/5.18 ml) cyclohexanone and 0.075 mol (5.78 g) ammonium acetate in 50 ml of absolute ethanol. The mixture was gently warmed on a hot plate with medium stirring and stirring was continued for about 15 h at a temperature of 303–308 K (30–35° C). After 12 h, the product formed was a spongy solid which was stirred for an additional 3 h until the reaction was complete as confirmed by the absence of aldehyde and cyclohexanone in the reaction mixture by TLC. After this, the crude compound was separated by filtration and washed with a 1:5 ethanol-ether mixture. X-ray diffraction quality crystals of 2,4-bis(3-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one were obtained by slow evaporation from ethanol.

Refinement

The nitrogen H atom was located in a difference Fourier map and refined isotropically. Other hydrogen atoms were fixed geometrically and allowed to ride on the parent carbon atoms with aromatic C-H = 0.93 Å, aliphatic C-H = 0.98 Å, methylene C-H = 0.97 Å and methyl C-H = 0.96 Å. The displacement parameters were set for phenyl, methylene and aliphatic H atoms at Uiso(H) = 1.2Ueq(C) and for methyl H atoms at Uiso(H) = 1.5Ueq(C)

Figures

Fig. 1.
Anistropic displacement representation of the molecule with atoms represented with 30% probability ellipsoids.
Fig. 2.
Packing diagram showing the N-H···O hydrogen bonding (green dashed lines) parallel to the b-axis.

Crystal data

C22H25NO3F(000) = 752
Mr = 351.43Dx = 1.266 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2453 reflections
a = 22.3843 (9) Åθ = 2.9–22.7°
b = 6.5666 (3) ŵ = 0.08 mm1
c = 13.0745 (4) ÅT = 298 K
β = 106.382 (2)°Block, colourless
V = 1843.78 (13) Å30.40 × 0.28 × 0.15 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer3971 independent reflections
Radiation source: fine-focus sealed tube2326 reflections with I > 2σ(I)
graphiteRint = 0.037
phi and ω scansθmax = 28.3°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 1999)h = −27→28
Tmin = 0.967, Tmax = 0.988k = −7→8
12835 measured reflectionsl = −12→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0643P)2] where P = (Fo2 + 2Fc2)/3
3971 reflections(Δ/σ)max < 0.001
241 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = −0.23 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)

xyzUiso*/Ueq
C10.32467 (7)0.5186 (3)0.49436 (13)0.0356 (4)
H10.34710.64830.50980.043*
C20.30802 (8)0.4800 (3)0.37207 (13)0.0388 (5)
H20.34640.48570.35020.047*
C30.27531 (9)0.2775 (3)0.33443 (15)0.0479 (5)
H3A0.27240.25890.25960.057*
H3B0.30050.16740.37370.057*
C40.21054 (10)0.2635 (3)0.34870 (16)0.0573 (6)
H4A0.18920.14780.30850.069*
H4B0.21410.23930.42340.069*
C50.17173 (9)0.4527 (3)0.31292 (15)0.0484 (5)
H5A0.13560.44690.33980.058*
H5B0.15690.45290.23570.058*
C60.20648 (8)0.6525 (3)0.34984 (13)0.0398 (4)
H60.18070.76600.31330.048*
C70.22453 (7)0.6922 (3)0.47199 (13)0.0376 (4)
H70.24600.82370.48600.045*
C80.26600 (8)0.6491 (3)0.31776 (13)0.0382 (4)
C90.36693 (7)0.3516 (3)0.55456 (12)0.0351 (4)
C100.34445 (8)0.1866 (3)0.59844 (13)0.0430 (5)
H100.30240.17960.59470.052*
C110.38393 (9)0.0330 (3)0.64743 (15)0.0495 (5)
H110.3682−0.07610.67710.059*
C120.44674 (9)0.0379 (3)0.65342 (14)0.0489 (5)
H120.4732−0.06640.68690.059*
C130.46919 (8)0.2005 (3)0.60884 (14)0.0419 (5)
C140.42955 (8)0.3570 (3)0.56051 (13)0.0386 (4)
H140.44530.46710.53170.046*
C150.16734 (8)0.7034 (3)0.51186 (13)0.0371 (4)
C160.13403 (8)0.8838 (3)0.50128 (15)0.0473 (5)
H160.14710.99580.46970.057*
C170.08192 (9)0.8993 (3)0.53688 (16)0.0532 (5)
H170.06041.02200.52960.064*
C180.06116 (8)0.7346 (3)0.58332 (15)0.0478 (5)
H180.02580.74510.60700.057*
C190.09401 (8)0.5548 (3)0.59381 (14)0.0409 (5)
C200.14652 (8)0.5399 (3)0.55826 (14)0.0403 (5)
H200.16810.41730.56580.048*
C210.57145 (9)0.0580 (3)0.65086 (19)0.0692 (7)
H21A0.57470.04310.72530.104*
H21B0.61180.08680.64230.104*
H21C0.5557−0.06590.61410.104*
C220.03130 (10)0.3935 (4)0.69181 (18)0.0737 (7)
H22A0.04290.49370.74740.111*
H22B0.02680.26330.72230.111*
H22C−0.00750.43170.64210.111*
N10.26760 (6)0.5346 (2)0.52819 (12)0.0370 (4)
O10.27803 (6)0.7680 (2)0.25553 (10)0.0548 (4)
O20.53008 (6)0.2212 (2)0.60764 (11)0.0612 (4)
O30.07815 (6)0.3815 (2)0.63810 (11)0.0613 (4)
H1N0.2775 (8)0.558 (3)0.5980 (15)0.048 (6)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0318 (9)0.0366 (11)0.0398 (10)0.0004 (8)0.0123 (8)−0.0011 (8)
C20.0399 (10)0.0469 (12)0.0347 (10)0.0054 (9)0.0190 (8)0.0037 (8)
C30.0630 (13)0.0441 (12)0.0381 (10)0.0039 (10)0.0168 (9)−0.0040 (9)
C40.0650 (14)0.0463 (13)0.0560 (13)−0.0119 (11)0.0097 (11)−0.0059 (10)
C50.0440 (11)0.0584 (14)0.0405 (11)−0.0084 (10)0.0083 (9)−0.0056 (10)
C60.0372 (10)0.0426 (11)0.0390 (10)0.0050 (8)0.0096 (8)0.0064 (9)
C70.0341 (9)0.0372 (11)0.0428 (10)0.0001 (8)0.0128 (8)−0.0016 (8)
C80.0431 (10)0.0402 (11)0.0314 (9)−0.0028 (9)0.0107 (8)0.0010 (9)
C90.0369 (10)0.0408 (11)0.0293 (9)0.0022 (8)0.0120 (7)−0.0016 (8)
C100.0375 (10)0.0547 (13)0.0401 (10)0.0012 (9)0.0165 (8)0.0066 (9)
C110.0554 (12)0.0529 (13)0.0456 (12)0.0049 (10)0.0229 (10)0.0154 (10)
C120.0512 (12)0.0535 (13)0.0420 (11)0.0125 (10)0.0133 (9)0.0123 (10)
C130.0333 (10)0.0524 (13)0.0400 (10)0.0034 (9)0.0101 (8)−0.0009 (9)
C140.0362 (10)0.0417 (11)0.0392 (10)0.0000 (8)0.0128 (8)0.0021 (9)
C150.0339 (9)0.0407 (11)0.0357 (9)0.0034 (8)0.0081 (8)−0.0037 (8)
C160.0430 (11)0.0400 (12)0.0612 (13)0.0041 (9)0.0184 (9)0.0037 (10)
C170.0451 (12)0.0464 (13)0.0692 (14)0.0152 (10)0.0177 (10)0.0001 (11)
C180.0355 (10)0.0562 (14)0.0537 (12)0.0086 (10)0.0162 (9)−0.0021 (10)
C190.0383 (10)0.0435 (12)0.0414 (11)0.0041 (9)0.0121 (8)0.0005 (9)
C200.0382 (10)0.0389 (11)0.0452 (11)0.0104 (8)0.0140 (8)0.0008 (9)
C210.0418 (12)0.0740 (17)0.0868 (17)0.0182 (11)0.0098 (11)0.0064 (13)
C220.0694 (15)0.0840 (19)0.0840 (17)0.0043 (13)0.0481 (14)0.0144 (14)
N10.0325 (8)0.0488 (10)0.0313 (9)0.0070 (7)0.0114 (7)−0.0019 (7)
O10.0582 (9)0.0581 (10)0.0507 (8)−0.0021 (7)0.0194 (7)0.0200 (7)
O20.0350 (8)0.0656 (10)0.0832 (11)0.0114 (7)0.0167 (7)0.0151 (8)
O30.0600 (9)0.0554 (10)0.0812 (10)0.0095 (7)0.0406 (8)0.0162 (8)

Geometric parameters (Å, °)

C1—N11.469 (2)C11—C121.386 (3)
C1—C91.516 (2)C11—H110.9300
C1—C21.557 (2)C12—C131.378 (3)
C1—H10.9800C12—H120.9300
C2—C81.498 (2)C13—O21.374 (2)
C2—C31.531 (2)C13—C141.388 (2)
C2—H20.9800C14—H140.9300
C3—C41.516 (3)C15—C201.378 (2)
C3—H3A0.9700C15—C161.385 (2)
C3—H3B0.9700C16—C171.376 (2)
C4—C51.512 (3)C16—H160.9300
C4—H4A0.9700C17—C181.383 (3)
C4—H4B0.9700C17—H170.9300
C5—C61.532 (2)C18—C191.378 (2)
C5—H5A0.9700C18—H180.9300
C5—H5B0.9700C19—O31.368 (2)
C6—C81.506 (2)C19—C201.384 (2)
C6—C71.555 (2)C20—H200.9300
C6—H60.9800C21—O21.425 (2)
C7—N11.463 (2)C21—H21A0.9600
C7—C151.514 (2)C21—H21B0.9600
C7—H70.9800C21—H21C0.9600
C8—O11.2119 (19)C22—O31.419 (2)
C9—C141.382 (2)C22—H22A0.9600
C9—C101.386 (2)C22—H22B0.9600
C10—C111.374 (2)C22—H22C0.9600
C10—H100.9300N1—H1N0.890 (18)
N1—C1—C9111.34 (13)C11—C10—H10119.8
N1—C1—C2110.15 (13)C9—C10—H10119.8
C9—C1—C2110.43 (13)C10—C11—C12121.21 (18)
N1—C1—H1108.3C10—C11—H11119.4
C9—C1—H1108.3C12—C11—H11119.4
C2—C1—H1108.3C13—C12—C11118.63 (18)
C8—C2—C3108.17 (15)C13—C12—H12120.7
C8—C2—C1107.60 (13)C11—C12—H12120.7
C3—C2—C1115.21 (14)O2—C13—C12124.24 (17)
C8—C2—H2108.6O2—C13—C14115.51 (16)
C3—C2—H2108.6C12—C13—C14120.25 (16)
C1—C2—H2108.6C9—C14—C13120.99 (17)
C4—C3—C2113.59 (15)C9—C14—H14119.5
C4—C3—H3A108.8C13—C14—H14119.5
C2—C3—H3A108.8C20—C15—C16118.10 (16)
C4—C3—H3B108.8C20—C15—C7122.51 (16)
C2—C3—H3B108.8C16—C15—C7119.40 (16)
H3A—C3—H3B107.7C17—C16—C15120.87 (18)
C5—C4—C3113.46 (16)C17—C16—H16119.6
C5—C4—H4A108.9C15—C16—H16119.6
C3—C4—H4A108.9C16—C17—C18120.83 (18)
C5—C4—H4B108.9C16—C17—H17119.6
C3—C4—H4B108.9C18—C17—H17119.6
H4A—C4—H4B107.7C19—C18—C17118.55 (17)
C4—C5—C6114.18 (15)C19—C18—H18120.7
C4—C5—H5A108.7C17—C18—H18120.7
C6—C5—H5A108.7O3—C19—C18124.06 (16)
C4—C5—H5B108.7O3—C19—C20115.45 (16)
C6—C5—H5B108.7C18—C19—C20120.48 (17)
H5A—C5—H5B107.6C15—C20—C19121.17 (16)
C8—C6—C5108.04 (15)C15—C20—H20119.4
C8—C6—C7107.14 (13)C19—C20—H20119.4
C5—C6—C7115.39 (14)O2—C21—H21A109.5
C8—C6—H6108.7O2—C21—H21B109.5
C5—C6—H6108.7H21A—C21—H21B109.5
C7—C6—H6108.7O2—C21—H21C109.5
N1—C7—C15111.28 (14)H21A—C21—H21C109.5
N1—C7—C6109.93 (14)H21B—C21—H21C109.5
C15—C7—C6111.21 (13)O3—C22—H22A109.5
N1—C7—H7108.1O3—C22—H22B109.5
C15—C7—H7108.1H22A—C22—H22B109.5
C6—C7—H7108.1O3—C22—H22C109.5
O1—C8—C2124.55 (16)H22A—C22—H22C109.5
O1—C8—C6123.99 (16)H22B—C22—H22C109.5
C2—C8—C6111.46 (14)C7—N1—C1113.91 (13)
C14—C9—C10118.53 (17)C7—N1—H1N109.3 (12)
C14—C9—C1119.04 (16)C1—N1—H1N109.6 (11)
C10—C9—C1122.31 (15)C13—O2—C21117.20 (16)
C11—C10—C9120.39 (17)C19—O3—C22118.64 (15)
N1—C1—C2—C856.22 (18)C10—C11—C12—C13−0.1 (3)
C9—C1—C2—C8179.60 (13)C11—C12—C13—O2−178.66 (17)
N1—C1—C2—C3−64.51 (19)C11—C12—C13—C141.0 (3)
C9—C1—C2—C358.88 (19)C10—C9—C14—C130.3 (3)
C8—C2—C3—C4−53.64 (19)C1—C9—C14—C13−175.81 (15)
C1—C2—C3—C466.8 (2)O2—C13—C14—C9178.61 (16)
C2—C3—C4—C545.2 (2)C12—C13—C14—C9−1.0 (3)
C3—C4—C5—C6−44.8 (2)N1—C7—C15—C20−25.2 (2)
C4—C5—C6—C852.4 (2)C6—C7—C15—C2097.7 (2)
C4—C5—C6—C7−67.4 (2)N1—C7—C15—C16155.10 (16)
C8—C6—C7—N1−57.64 (18)C6—C7—C15—C16−82.0 (2)
C5—C6—C7—N162.69 (18)C20—C15—C16—C170.5 (3)
C8—C6—C7—C15178.66 (15)C7—C15—C16—C17−179.85 (16)
C5—C6—C7—C15−61.0 (2)C15—C16—C17—C18−0.6 (3)
C3—C2—C8—O1−116.08 (19)C16—C17—C18—C190.4 (3)
C1—C2—C8—O1118.86 (18)C17—C18—C19—O3−179.87 (18)
C3—C2—C8—C663.68 (17)C17—C18—C19—C20−0.2 (3)
C1—C2—C8—C6−61.37 (18)C16—C15—C20—C19−0.3 (3)
C5—C6—C8—O1116.90 (19)C7—C15—C20—C19−179.91 (15)
C7—C6—C8—O1−118.19 (18)O3—C19—C20—C15179.84 (16)
C5—C6—C8—C2−62.87 (18)C18—C19—C20—C150.1 (3)
C7—C6—C8—C262.04 (19)C15—C7—N1—C1−178.96 (13)
N1—C1—C9—C14−158.74 (15)C6—C7—N1—C157.38 (18)
C2—C1—C9—C1478.57 (19)C9—C1—N1—C7−179.40 (14)
N1—C1—C9—C1025.3 (2)C2—C1—N1—C7−56.55 (19)
C2—C1—C9—C10−97.36 (18)C12—C13—O2—C213.2 (3)
C14—C9—C10—C110.5 (3)C14—C13—O2—C21−176.39 (17)
C1—C9—C10—C11176.49 (16)C18—C19—O3—C22−10.4 (3)
C9—C10—C11—C12−0.6 (3)C20—C19—O3—C22169.87 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.890 (18)2.352 (18)3.1901 (19)157.0 (16)

Symmetry codes: (i) x, −y+3/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2238).

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