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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3188.
Published online 2009 November 25. doi:  10.1107/S1600536809049447
PMCID: PMC2972086

Methyl 9-p-tolyl-8a,9,9a,10,11,12,13,14a-octa­hydro-8H-benzo[f]chromeno[3,4-b]indolizine-8a-carboxyl­ate

Abstract

In the title compound, C28H29NO3, the fused pyrrolidine and piperidine rings of the octa­hydro­indolizine unit exhibit envelope and chair conformations, respectively. The dihedral angle between the naphthalene ring system and the benzene ring is 40.37 (5)°. The crystal packing is stabilized by weak inter­molecular C—H(...)O inter­actions.

Related literature

For the biological activity of indolizine derivatives, see: Campagna et al. (1990 [triangle]); Malonne et al. (1998 [triangle]); Medda et al. (2003 [triangle]); Pearson & Guo (2001 [triangle]); Sonnet et al. (2000 [triangle]). For related structures, see: Gunasekaran et al. (2009 [triangle]); Kamala et al. (2009 [triangle]). For details of ring conformations, see: Cremer & Pople (1975 [triangle]); Nardelli (1983 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o3188-scheme1.jpg

Experimental

Crystal data

  • C28H29NO3
  • M r = 427.52
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3188-efi1.jpg
  • a = 11.4842 (9) Å
  • b = 23.0129 (14) Å
  • c = 9.1642 (5) Å
  • β = 112.725 (2)°
  • V = 2233.9 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.30 × 0.20 × 0.20 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.976, T max = 0.984
  • 27595 measured reflections
  • 5875 independent reflections
  • 3629 reflections with I > 2σ(I)
  • R int = 0.044

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.141
  • S = 1.01
  • 5875 reflections
  • 291 parameters
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [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/S1600536809049447/is2492sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049447/is2492Isup2.hkl

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

Acknowledgments

BG thanks AMET University management, India, for their kind support. BG also acknowledge SAIF, IITMadras, India, for the data collection.

supplementary crystallographic information

Comment

The synthesis of biologically active indolizine derivatives continues to attract the attention of organic chemists, because of their wide spectrum of biological activity. Indolizine derivatives have been found to possess a variety of biological activities such as antiinflammatory (Malonne et al., 1998), antiviral (Medda et al., 2003), aromatase inhibitory (Sonnet et al., 2000), analgestic (Campagna et al., 1990) and antitumor (Pearson & Guo, 2001) activities.

The geometric parameters of the title compound (Fig. 1) agree well with reported similar structures (Gunasekaran et al., 2009; Kamala et al., 2009). The mean plane of the naphthalene ring system makes a dihedral angle of 40.37 (5)° with the methyl benzene ring. In the molecule the pyrrolidine ring N1/C13/C12/C19/C18 exhibits an envelope conformation with envelope on C13 with an asymmetry parameter (Nardelli, 1983) ΔCs (C13) = 14.17 (3) and with the puckering parameters (Cremer & Pople, 1975) q2 = 0.4960 (2) Å and [var phi]2 = 205.68 (9)°. The six membered ring N1/C14—C18 exhibits chair conformation with asymmetry parameters ΔCs (N1) = 1.78 (1)/(C16) = 1.78 (1) and with the puckering parameters Q = 0.5855 (2) Å, Θ = 3.86 (3)° and [var phi] = 335.84 (8)°. The sum of bond angles around N1 [333.20 (12)°] indicates sp3 hybridization. The crystal packing is stabilized by weak intermolecular C—H···O interactions.

Experimental

A mixture of (Z)-methyl 2-[(1-formylnaphthalen-2-yloxy)methyl]-3-tolylacrylate (20 mmol) and pipecolinic acid (30 mmol) were refluxed in benzene for 20 h and the solvent was removed under reduced pressure. The crude product was subjected to column chromatography to get the pure product. Chloroform and methanol (1:1) solvent mixture was used for the crystallization under slow evaporation method.

Refinement

H atoms were positioned geometrically and refined using riding model, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.98 Å and Uiso(H) = 1.2Ueq(C) for C—H, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2, and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for CH3.

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
Fig. 2.
The packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C28H29NO3F(000) = 912
Mr = 427.52Dx = 1.271 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4649 reflections
a = 11.4842 (9) Åθ = 2.6–26.3°
b = 23.0129 (14) ŵ = 0.08 mm1
c = 9.1642 (5) ÅT = 293 K
β = 112.725 (2)°Block, colourless
V = 2233.9 (3) Å30.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker Kappa APEXII CCD diffractometer5875 independent reflections
Radiation source: fine-focus sealed tube3629 reflections with I > 2σ(I)
graphiteRint = 0.044
ω and [var phi] scansθmax = 28.9°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −15→15
Tmin = 0.976, Tmax = 0.984k = −31→31
27595 measured reflectionsl = −12→12

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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0608P)2 + 0.3616P] where P = (Fo2 + 2Fc2)/3
5875 reflections(Δ/σ)max = 0.001
291 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = −0.17 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C10.61198 (18)−0.14947 (8)0.0295 (2)0.0504 (4)
H10.5640−0.12760.07110.061*
C20.5662 (2)−0.20144 (9)−0.0413 (2)0.0670 (6)
H20.4879−0.2144−0.04690.080*
C30.6357 (3)−0.23540 (9)−0.1053 (3)0.0771 (7)
H30.6043−0.2710−0.15190.093*
C40.7483 (2)−0.21626 (9)−0.0990 (2)0.0676 (6)
H40.7938−0.2389−0.14240.081*
C50.79886 (19)−0.16256 (8)−0.02817 (19)0.0497 (5)
C60.91374 (19)−0.14077 (9)−0.0278 (2)0.0545 (5)
H60.9598−0.1630−0.07140.065*
C70.95803 (17)−0.08848 (8)0.0344 (2)0.0490 (4)
H71.0328−0.07440.03070.059*
C80.89125 (15)−0.05504 (7)0.10510 (17)0.0383 (4)
C90.78070 (15)−0.07379 (7)0.11318 (16)0.0354 (3)
C100.73006 (16)−0.12828 (7)0.04091 (17)0.0399 (4)
C110.89693 (14)0.02897 (7)0.25903 (17)0.0391 (4)
H11A0.92690.06880.27020.047*
H11B0.92950.01120.36310.047*
C120.75363 (14)0.02882 (7)0.19453 (16)0.0339 (3)
C130.71155 (14)−0.03487 (6)0.18493 (16)0.0331 (3)
H130.6204−0.03760.12360.040*
C140.70537 (18)−0.10215 (7)0.39732 (18)0.0460 (4)
H14A0.7485−0.13260.36450.055*
H14B0.6151−0.10840.34470.055*
C150.74380 (19)−0.10420 (8)0.57578 (19)0.0541 (5)
H15A0.7177−0.14100.60510.065*
H15B0.8350−0.10160.62740.065*
C160.6842 (2)−0.05474 (8)0.6322 (2)0.0574 (5)
H16A0.7163−0.05490.74680.069*
H16B0.5935−0.06030.59240.069*
C170.71307 (19)0.00345 (8)0.57545 (18)0.0509 (5)
H17A0.80280.01160.62540.061*
H17B0.66790.03420.60390.061*
C180.67275 (16)0.00141 (7)0.39653 (17)0.0387 (4)
H180.5824−0.00760.35060.046*
C190.69420 (15)0.05562 (7)0.30745 (17)0.0388 (4)
H190.60960.06860.23800.047*
C200.75513 (17)0.10776 (7)0.41025 (17)0.0418 (4)
C210.88099 (18)0.11218 (8)0.51269 (19)0.0511 (5)
H210.93630.08220.51620.061*
C220.92615 (19)0.15999 (8)0.60945 (19)0.0512 (5)
H221.01150.16180.67420.061*
C230.8483 (2)0.20499 (7)0.6126 (2)0.0521 (5)
C240.7237 (2)0.20078 (8)0.5124 (2)0.0610 (5)
H240.66860.23060.51130.073*
C250.67736 (19)0.15346 (8)0.4128 (2)0.0527 (5)
H250.59240.15240.34640.063*
C260.8973 (3)0.25562 (9)0.7251 (2)0.0732 (7)
H26A0.86260.29120.67090.110*
H26B0.98770.25690.76260.110*
H26C0.87250.25090.81320.110*
C270.69921 (15)0.05766 (7)0.03259 (17)0.0369 (4)
C280.7123 (2)0.13788 (8)−0.1198 (2)0.0593 (5)
H28A0.72750.1141−0.19670.089*
H28B0.75710.1739−0.10820.089*
H28C0.62350.1455−0.15440.089*
N10.73871 (12)−0.04567 (6)0.35365 (13)0.0366 (3)
O10.94386 (11)−0.00186 (5)0.15779 (13)0.0454 (3)
O20.61520 (12)0.03875 (6)−0.07961 (14)0.0632 (4)
O30.75561 (12)0.10804 (5)0.02989 (13)0.0535 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0596 (12)0.0466 (10)0.0456 (9)−0.0086 (9)0.0208 (8)−0.0026 (8)
C20.0793 (15)0.0566 (12)0.0630 (12)−0.0200 (11)0.0252 (11)−0.0058 (10)
C30.115 (2)0.0444 (12)0.0684 (13)−0.0130 (13)0.0313 (14)−0.0120 (10)
C40.1003 (18)0.0460 (12)0.0592 (11)0.0105 (12)0.0339 (12)−0.0069 (9)
C50.0691 (13)0.0446 (10)0.0366 (8)0.0111 (9)0.0217 (8)0.0039 (7)
C60.0656 (13)0.0611 (12)0.0451 (9)0.0219 (10)0.0304 (9)0.0034 (8)
C70.0449 (10)0.0642 (12)0.0454 (9)0.0113 (9)0.0258 (8)0.0085 (8)
C80.0389 (9)0.0435 (9)0.0336 (7)0.0040 (8)0.0152 (6)0.0039 (6)
C90.0386 (9)0.0391 (8)0.0296 (7)0.0032 (7)0.0144 (6)0.0041 (6)
C100.0508 (10)0.0377 (9)0.0304 (7)0.0023 (8)0.0150 (7)0.0036 (6)
C110.0351 (9)0.0422 (9)0.0374 (7)−0.0008 (7)0.0113 (6)−0.0001 (7)
C120.0320 (8)0.0387 (8)0.0292 (6)0.0017 (7)0.0099 (6)0.0004 (6)
C130.0324 (8)0.0383 (8)0.0292 (6)0.0000 (7)0.0125 (6)0.0015 (6)
C140.0553 (11)0.0462 (10)0.0397 (8)−0.0017 (8)0.0220 (8)0.0044 (7)
C150.0643 (12)0.0605 (12)0.0383 (8)−0.0025 (10)0.0208 (8)0.0105 (8)
C160.0710 (13)0.0708 (13)0.0368 (8)−0.0016 (11)0.0278 (9)0.0028 (8)
C170.0609 (12)0.0597 (12)0.0347 (8)0.0025 (9)0.0212 (8)−0.0021 (8)
C180.0367 (9)0.0477 (10)0.0331 (7)0.0026 (7)0.0150 (6)−0.0014 (6)
C190.0368 (9)0.0442 (9)0.0326 (7)0.0081 (7)0.0104 (6)0.0010 (6)
C200.0523 (11)0.0394 (9)0.0342 (7)0.0095 (8)0.0173 (7)0.0039 (6)
C210.0572 (11)0.0440 (10)0.0420 (8)0.0136 (9)0.0080 (8)−0.0043 (8)
C220.0644 (12)0.0451 (10)0.0382 (8)0.0018 (9)0.0134 (8)−0.0016 (7)
C230.0826 (15)0.0382 (10)0.0439 (9)0.0005 (10)0.0338 (10)0.0023 (7)
C240.0805 (16)0.0423 (10)0.0721 (13)0.0186 (10)0.0425 (12)0.0021 (9)
C250.0571 (12)0.0490 (11)0.0547 (10)0.0142 (9)0.0245 (9)0.0023 (8)
C260.121 (2)0.0436 (11)0.0669 (12)−0.0086 (12)0.0488 (13)−0.0079 (9)
C270.0357 (9)0.0408 (9)0.0342 (7)0.0030 (7)0.0134 (7)0.0018 (6)
C280.0722 (14)0.0531 (11)0.0492 (10)0.0007 (10)0.0197 (9)0.0172 (9)
N10.0424 (8)0.0394 (7)0.0310 (6)0.0016 (6)0.0173 (5)0.0024 (5)
O10.0378 (7)0.0524 (7)0.0517 (6)−0.0038 (6)0.0234 (5)−0.0031 (5)
O20.0601 (8)0.0701 (9)0.0386 (6)−0.0181 (7)−0.0037 (6)0.0108 (6)
O30.0660 (9)0.0462 (7)0.0395 (6)−0.0111 (6)0.0108 (6)0.0080 (5)

Geometric parameters (Å, °)

C1—C21.365 (3)C15—H15A0.9700
C1—C101.406 (2)C15—H15B0.9700
C1—H10.9300C16—C171.519 (2)
C2—C31.397 (3)C16—H16A0.9700
C2—H20.9300C16—H16B0.9700
C3—C41.346 (3)C17—C181.523 (2)
C3—H30.9300C17—H17A0.9700
C4—C51.412 (3)C17—H17B0.9700
C4—H40.9300C18—N11.460 (2)
C5—C61.410 (3)C18—C191.562 (2)
C5—C101.426 (2)C18—H180.9800
C6—C71.344 (3)C19—C201.519 (2)
C6—H60.9300C19—H190.9800
C7—C81.409 (2)C20—C251.386 (2)
C7—H70.9300C20—C211.390 (2)
C8—O11.3678 (19)C21—C221.382 (2)
C8—C91.370 (2)C21—H210.9300
C9—C101.432 (2)C22—C231.375 (3)
C9—C131.506 (2)C22—H220.9300
C11—O11.4286 (18)C23—C241.373 (3)
C11—C121.519 (2)C23—C261.513 (3)
C11—H11A0.9700C24—C251.388 (3)
C11—H11B0.9700C24—H240.9300
C12—C271.522 (2)C25—H250.9300
C12—C131.535 (2)C26—H26A0.9600
C12—C191.569 (2)C26—H26B0.9600
C13—N11.4755 (17)C26—H26C0.9600
C13—H130.9800C27—O21.1878 (19)
C14—N11.454 (2)C27—O31.3329 (19)
C14—C151.521 (2)C28—O31.4404 (19)
C14—H14A0.9700C28—H28A0.9600
C14—H14B0.9700C28—H28B0.9600
C15—C161.518 (3)C28—H28C0.9600
C2—C1—C10121.47 (19)C15—C16—H16A109.4
C2—C1—H1119.3C17—C16—H16A109.4
C10—C1—H1119.3C15—C16—H16B109.4
C1—C2—C3120.8 (2)C17—C16—H16B109.4
C1—C2—H2119.6H16A—C16—H16B108.0
C3—C2—H2119.6C16—C17—C18109.00 (14)
C4—C3—C2119.6 (2)C16—C17—H17A109.9
C4—C3—H3120.2C18—C17—H17A109.9
C2—C3—H3120.2C16—C17—H17B109.9
C3—C4—C5121.6 (2)C18—C17—H17B109.9
C3—C4—H4119.2H17A—C17—H17B108.3
C5—C4—H4119.2N1—C18—C17109.83 (13)
C6—C5—C4122.05 (18)N1—C18—C19104.42 (11)
C6—C5—C10118.72 (16)C17—C18—C19119.63 (14)
C4—C5—C10119.20 (19)N1—C18—H18107.5
C7—C6—C5121.31 (16)C17—C18—H18107.5
C7—C6—H6119.3C19—C18—H18107.5
C5—C6—H6119.3C20—C19—C18115.77 (12)
C6—C7—C8119.99 (17)C20—C19—C12120.39 (14)
C6—C7—H7120.0C18—C19—C12103.14 (12)
C8—C7—H7120.0C20—C19—H19105.4
O1—C8—C9123.71 (14)C18—C19—H19105.4
O1—C8—C7113.99 (14)C12—C19—H19105.4
C9—C8—C7122.24 (16)C25—C20—C21116.22 (16)
C8—C9—C10118.03 (14)C25—C20—C19117.67 (16)
C8—C9—C13119.49 (14)C21—C20—C19125.90 (15)
C10—C9—C13122.28 (14)C22—C21—C20121.74 (17)
C1—C10—C5117.31 (16)C22—C21—H21119.1
C1—C10—C9123.05 (15)C20—C21—H21119.1
C5—C10—C9119.60 (16)C23—C22—C21121.79 (18)
O1—C11—C12111.72 (12)C23—C22—H22119.1
O1—C11—H11A109.3C21—C22—H22119.1
C12—C11—H11A109.3C24—C23—C22116.82 (17)
O1—C11—H11B109.3C24—C23—C26121.77 (19)
C12—C11—H11B109.3C22—C23—C26121.4 (2)
H11A—C11—H11B107.9C23—C24—C25122.03 (18)
C11—C12—C27110.70 (12)C23—C24—H24119.0
C11—C12—C13107.11 (13)C25—C24—H24119.0
C27—C12—C13111.03 (12)C20—C25—C24121.38 (19)
C11—C12—C19115.12 (12)C20—C25—H25119.3
C27—C12—C19110.62 (12)C24—C25—H25119.3
C13—C12—C19101.87 (12)C23—C26—H26A109.5
N1—C13—C9115.07 (12)C23—C26—H26B109.5
N1—C13—C1299.57 (11)H26A—C26—H26B109.5
C9—C13—C12112.67 (12)C23—C26—H26C109.5
N1—C13—H13109.7H26A—C26—H26C109.5
C9—C13—H13109.7H26B—C26—H26C109.5
C12—C13—H13109.7O2—C27—O3122.72 (14)
N1—C14—C15109.00 (14)O2—C27—C12125.07 (15)
N1—C14—H14A109.9O3—C27—C12112.20 (13)
C15—C14—H14A109.9O3—C28—H28A109.5
N1—C14—H14B109.9O3—C28—H28B109.5
C15—C14—H14B109.9H28A—C28—H28B109.5
H14A—C14—H14B108.3O3—C28—H28C109.5
C16—C15—C14111.17 (15)H28A—C28—H28C109.5
C16—C15—H15A109.4H28B—C28—H28C109.5
C14—C15—H15A109.4C14—N1—C18111.72 (12)
C16—C15—H15B109.4C14—N1—C13117.86 (12)
C14—C15—H15B109.4C18—N1—C13103.62 (11)
H15A—C15—H15B108.0C8—O1—C11116.59 (12)
C15—C16—C17110.99 (14)C27—O3—C28116.17 (13)
C10—C1—C2—C3−0.1 (3)N1—C18—C19—C1210.03 (14)
C1—C2—C3—C4−0.9 (3)C17—C18—C19—C12133.35 (15)
C2—C3—C4—C50.4 (3)C11—C12—C19—C2036.45 (19)
C3—C4—C5—C6−176.85 (19)C27—C12—C19—C20−89.96 (16)
C3—C4—C5—C101.1 (3)C13—C12—C19—C20151.96 (13)
C4—C5—C6—C7177.23 (17)C11—C12—C19—C18−94.42 (15)
C10—C5—C6—C7−0.8 (3)C27—C12—C19—C18139.17 (13)
C5—C6—C7—C81.9 (3)C13—C12—C19—C1821.08 (14)
C6—C7—C8—O1−177.48 (15)C18—C19—C20—C25−101.78 (17)
C6—C7—C8—C9−0.1 (2)C12—C19—C20—C25133.08 (16)
O1—C8—C9—C10174.48 (13)C18—C19—C20—C2172.7 (2)
C7—C8—C9—C10−2.6 (2)C12—C19—C20—C21−52.4 (2)
O1—C8—C9—C13−0.6 (2)C25—C20—C21—C22−1.1 (3)
C7—C8—C9—C13−177.70 (13)C19—C20—C21—C22−175.66 (16)
C2—C1—C10—C51.6 (2)C20—C21—C22—C231.8 (3)
C2—C1—C10—C9179.52 (16)C21—C22—C23—C24−1.3 (3)
C6—C5—C10—C1175.96 (15)C21—C22—C23—C26176.75 (17)
C4—C5—C10—C1−2.1 (2)C22—C23—C24—C250.2 (3)
C6—C5—C10—C9−2.0 (2)C26—C23—C24—C25−177.77 (17)
C4—C5—C10—C9179.92 (15)C21—C20—C25—C240.1 (3)
C8—C9—C10—C1−174.23 (15)C19—C20—C25—C24175.10 (16)
C13—C9—C10—C10.7 (2)C23—C24—C25—C200.4 (3)
C8—C9—C10—C53.6 (2)C11—C12—C27—O2133.84 (18)
C13—C9—C10—C5178.58 (13)C13—C12—C27—O215.0 (2)
O1—C11—C12—C27−60.21 (17)C19—C12—C27—O2−97.33 (19)
O1—C11—C12—C1360.97 (15)C11—C12—C27—O3−47.10 (18)
O1—C11—C12—C19173.42 (12)C13—C12—C27—O3−165.93 (12)
C8—C9—C13—N1−95.53 (16)C19—C12—C27—O381.74 (16)
C10—C9—C13—N189.59 (17)C15—C14—N1—C18−61.31 (18)
C8—C9—C13—C1217.69 (18)C15—C14—N1—C13178.87 (14)
C10—C9—C13—C12−157.18 (13)C17—C18—N1—C1463.40 (17)
C11—C12—C13—N176.82 (13)C19—C18—N1—C14−167.15 (12)
C27—C12—C13—N1−162.21 (12)C17—C18—N1—C13−168.72 (13)
C19—C12—C13—N1−44.41 (13)C19—C18—N1—C13−39.26 (14)
C11—C12—C13—C9−45.60 (15)C9—C13—N1—C14−62.47 (18)
C27—C12—C13—C975.37 (16)C12—C13—N1—C14176.84 (13)
C19—C12—C13—C9−166.83 (11)C9—C13—N1—C18173.56 (13)
N1—C14—C15—C1656.0 (2)C12—C13—N1—C1852.87 (14)
C14—C15—C16—C17−53.9 (2)C9—C8—O1—C1115.4 (2)
C15—C16—C17—C1854.2 (2)C7—C8—O1—C11−167.33 (13)
C16—C17—C18—N1−58.24 (18)C12—C11—O1—C8−46.71 (18)
C16—C17—C18—C19−178.89 (15)O2—C27—O3—C28−2.3 (2)
N1—C18—C19—C20−123.56 (14)C12—C27—O3—C28178.56 (14)
C17—C18—C19—C20−0.2 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C13—H13···O2i0.982.583.496 (2)156
C7—H7···O1ii0.932.553.198 (2)127

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2492).

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