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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2550.
Published online 2009 September 26. doi:  10.1107/S1600536809037994
PMCID: PMC2970191

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

Abstract

In the title compound, C27H26BrNO3, the mean plane of the naphthalene ring system makes a dihedral angle of 22.0 (1)° with the bromo-substituted benzene ring. The pyrrolidine and piperidine rings exhibit envelope and chair conformations, respectively. An inter­molecular C—H(...)Br inter­action is observed.

Related literature

For the biological activity of indolizine derivatives, see: Gundersen et al. (2003 [triangle]); Teklu et al. (2005 [triangle]); Foster et al. (1995 [triangle]); Malonne et al. (1998 [triangle]); Medda et al. (2003 [triangle]). For related structures, see: Gunasekaran et al. (2009 [triangle]); Kamala et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2550-scheme1.jpg

Experimental

Crystal data

  • C27H26BrNO3
  • M r = 492.40
  • Trigonal, An external file that holds a picture, illustration, etc.
Object name is e-65-o2550-efi1.jpg
  • a = 18.4405 (8) Å
  • c = 11.4828 (8) Å
  • V = 3381.6 (3) Å3
  • Z = 6
  • Mo Kα radiation
  • μ = 1.85 mm−1
  • T = 293 K
  • 0.25 × 0.20 × 0.20 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.654, T max = 0.708
  • 23085 measured reflections
  • 5338 independent reflections
  • 2509 reflections with I > 2σ(I)
  • R int = 0.113

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.108
  • S = 0.85
  • 5338 reflections
  • 290 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.85 e Å−3
  • Δρmin = −0.33 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/S1600536809037994/is2463sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037994/is2463Isup2.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, IIT Madras, India, for the data collection.

supplementary crystallographic information

Comment

Indolizine derivatives exhibit antioxidative (Teklu et al., 2005), antiherpes (Foster et al., 1995), anti-inflammatory (Malonne et al., 1998) and antiviral (Medda et al., 2003) activities. In addition, indolizines are used as antimycobacterial agents against mycobacterial tuberculosis (Gundersen et al., 2003).

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 naphthalene ring makes the dihedral angle of 22.0 (1)° with the benzene ring. The pyrrolidine ring exhibits an envelope conformation and the piperidine (N1/C14–C18) ring exhibits a chair conformation [C16—C15—C14—N1 = 56.3 (3)° and C16—C17—C18—N1 = -53.9 (3)°]. The sum of bond angles around N1 [338.3 (2)°] indicates sp3 hybridization.

Experimental

A mixture of (Z)-methyl 2-((1-formylnaphthalen-2-yloxy)methyl) -3-(4-bromophenyl)acrylate (20 mmol) and piperidine-2-carboxylic 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 CH, 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. The components of the anisotropic displacement parameters in direction of the bond of C1, C2, C26 and O2 were restrained to be equal within an effective standard deviation of 0.001 using the DELU command in SHELXL (Sheldrick, 2008).

Figures

Fig. 1.
The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.

Crystal data

C27H26BrNO3Dx = 1.451 Mg m3
Mr = 492.40Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3Cell parameters from 4759 reflections
Hall symbol: -P 3θ = 2.2–25.7°
a = 18.4405 (8) ŵ = 1.85 mm1
c = 11.4828 (8) ÅT = 293 K
V = 3381.6 (3) Å3Block, colourless
Z = 60.25 × 0.20 × 0.20 mm
F(000) = 1524

Data collection

Bruker Kappa APEXII CCD diffractometer5338 independent reflections
Radiation source: fine-focus sealed tube2509 reflections with I > 2σ(I)
graphiteRint = 0.113
Detector resolution: 0 pixels mm-1θmax = 27.8°, θmin = 2.2°
ω and [var phi] scansh = −22→24
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)k = −24→24
Tmin = 0.654, Tmax = 0.708l = −8→15
23085 measured reflections

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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 0.85w = 1/[σ2(Fo2) + (0.0452P)2] where P = (Fo2 + 2Fc2)/3
5338 reflections(Δ/σ)max < 0.001
290 parametersΔρmax = 0.85 e Å3
2 restraintsΔρmin = −0.33 e Å3

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

xyzUiso*/Ueq
C10.32587 (18)0.03952 (17)−0.2836 (3)0.0450 (7)
C20.2679 (2)0.0537 (2)−0.3441 (3)0.0616 (9)
H20.24010.0769−0.30500.074*
C30.2515 (3)0.0339 (2)−0.4604 (3)0.0850 (13)
H30.21230.0432−0.49820.102*
C40.2927 (3)0.0004 (2)−0.5221 (3)0.0859 (13)
H40.2821−0.0115−0.60110.103*
C50.3479 (3)−0.0149 (2)−0.4667 (3)0.0786 (12)
H50.3752−0.0375−0.50820.094*
C60.3654 (2)0.00269 (18)−0.3465 (3)0.0564 (9)
C70.4228 (2)−0.01415 (18)−0.2873 (3)0.0627 (10)
H70.4519−0.0349−0.32860.075*
C80.43567 (19)−0.00053 (17)−0.1725 (3)0.0513 (8)
H80.4704−0.0156−0.13360.062*
C90.39688 (17)0.03636 (16)−0.1111 (2)0.0384 (7)
C100.34630 (16)0.06057 (15)−0.1639 (2)0.0356 (7)
C110.32309 (16)0.11839 (16)−0.1002 (2)0.0341 (6)
H110.26690.1056−0.12420.041*
C120.32533 (15)0.11112 (16)0.0348 (2)0.0333 (6)
C130.34153 (18)0.04079 (17)0.0692 (2)0.0431 (7)
H13A0.35260.04380.15220.052*
H13B0.2920−0.01270.05310.052*
C140.41242 (18)0.23382 (17)−0.2399 (2)0.0434 (7)
H14A0.36500.2180−0.29120.052*
H14B0.44160.2053−0.26630.052*
C150.47016 (18)0.32660 (18)−0.2460 (2)0.0477 (8)
H15A0.43950.3550−0.22680.057*
H15B0.49140.3422−0.32470.057*
C160.54293 (18)0.35396 (18)−0.1621 (3)0.0492 (8)
H16A0.57650.3293−0.18500.059*
H16B0.57820.4144−0.16440.059*
C170.50984 (18)0.32634 (16)−0.0398 (2)0.0425 (7)
H17A0.55620.34040.01280.051*
H17B0.48150.3558−0.01400.051*
C180.44950 (16)0.23290 (15)−0.0361 (2)0.0329 (6)
H180.47990.2029−0.05080.039*
C190.39796 (15)0.19968 (16)0.0742 (2)0.0323 (6)
H190.37220.23420.08820.039*
C200.44263 (16)0.20142 (16)0.1853 (2)0.0326 (6)
C210.40965 (17)0.20588 (17)0.2912 (2)0.0395 (7)
H210.36120.20960.29250.047*
C220.44673 (19)0.20491 (18)0.3956 (2)0.0454 (8)
H220.42320.20720.46620.054*
C230.51857 (18)0.20047 (17)0.3933 (2)0.0414 (7)
C240.55532 (18)0.19869 (17)0.2895 (3)0.0461 (8)
H240.60530.19790.28880.055*
C250.51612 (17)0.19814 (17)0.1866 (2)0.0426 (7)
H250.53970.19550.11620.051*
C260.24417 (18)0.09807 (19)0.0883 (3)0.0456 (7)
C270.1435 (2)0.0356 (3)0.2332 (4)0.0985 (14)
H27A0.15330.08600.27140.148*
H27B0.1240−0.00910.28910.148*
H27C0.10210.02110.17350.148*
N10.38286 (13)0.20806 (12)−0.12185 (17)0.0301 (5)
O10.41141 (11)0.04609 (11)0.00670 (17)0.0446 (5)
O20.20524 (13)0.12926 (15)0.0531 (2)0.0685 (7)
O30.22148 (12)0.04877 (13)0.18093 (17)0.0569 (6)
Br10.56763 (2)0.19502 (2)0.53512 (3)0.06620 (16)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0421 (18)0.0299 (16)0.0472 (19)0.0063 (14)0.0072 (13)−0.0069 (14)
C20.056 (2)0.060 (2)0.052 (2)0.0171 (17)−0.0091 (16)−0.0117 (17)
C30.091 (3)0.073 (3)0.059 (3)0.016 (2)−0.019 (2)−0.012 (2)
C40.116 (4)0.060 (3)0.052 (3)0.021 (3)0.002 (3)−0.016 (2)
C50.110 (3)0.042 (2)0.061 (3)0.022 (2)0.020 (2)−0.0113 (19)
C60.070 (2)0.0282 (18)0.053 (2)0.0107 (17)0.0124 (18)−0.0059 (15)
C70.074 (3)0.0336 (19)0.077 (3)0.0245 (19)0.036 (2)0.0021 (18)
C80.056 (2)0.0335 (18)0.068 (2)0.0251 (16)0.0165 (18)0.0085 (16)
C90.0382 (17)0.0246 (15)0.0459 (19)0.0109 (14)0.0076 (14)0.0020 (13)
C100.0324 (16)0.0240 (15)0.0413 (17)0.0071 (13)0.0047 (13)−0.0016 (12)
C110.0281 (15)0.0342 (16)0.0382 (16)0.0142 (13)−0.0002 (12)−0.0010 (13)
C120.0313 (16)0.0295 (15)0.0368 (16)0.0134 (13)0.0027 (12)0.0023 (12)
C130.0474 (19)0.0340 (17)0.0440 (17)0.0175 (15)0.0040 (14)0.0025 (13)
C140.0450 (18)0.0462 (19)0.0402 (17)0.0236 (16)0.0022 (14)0.0055 (14)
C150.051 (2)0.046 (2)0.0464 (18)0.0243 (16)0.0104 (15)0.0115 (15)
C160.0425 (18)0.0320 (17)0.069 (2)0.0157 (15)0.0108 (16)0.0068 (15)
C170.0395 (18)0.0322 (16)0.0538 (19)0.0165 (14)−0.0031 (14)−0.0018 (14)
C180.0354 (16)0.0291 (15)0.0369 (15)0.0182 (13)−0.0024 (13)−0.0020 (12)
C190.0321 (16)0.0315 (15)0.0383 (16)0.0197 (13)−0.0019 (12)−0.0035 (12)
C200.0346 (16)0.0288 (15)0.0370 (16)0.0178 (13)−0.0026 (12)−0.0039 (12)
C210.0344 (16)0.0452 (18)0.0452 (18)0.0246 (15)−0.0037 (14)−0.0045 (14)
C220.050 (2)0.055 (2)0.0356 (17)0.0298 (17)−0.0023 (14)−0.0059 (14)
C230.0450 (19)0.0389 (18)0.0412 (18)0.0217 (15)−0.0112 (14)0.0008 (13)
C240.0398 (18)0.0508 (19)0.056 (2)0.0286 (16)−0.0092 (15)−0.0005 (15)
C250.0427 (18)0.0492 (19)0.0432 (18)0.0285 (15)−0.0001 (14)−0.0020 (14)
C260.0377 (18)0.0465 (19)0.0462 (19)0.0162 (14)0.0011 (14)−0.0031 (15)
C270.079 (3)0.108 (3)0.103 (3)0.043 (3)0.044 (2)0.021 (3)
N10.0292 (12)0.0280 (12)0.0332 (12)0.0143 (10)0.0022 (10)0.0007 (10)
O10.0462 (13)0.0353 (12)0.0571 (14)0.0238 (10)−0.0026 (10)−0.0004 (10)
O20.0512 (15)0.0940 (19)0.0727 (16)0.0455 (13)0.0179 (12)0.0238 (13)
O30.0493 (14)0.0684 (15)0.0484 (13)0.0260 (12)0.0151 (10)0.0127 (11)
Br10.0694 (3)0.0800 (3)0.0538 (2)0.0408 (2)−0.01750 (18)0.00658 (18)

Geometric parameters (Å, °)

C1—C21.406 (4)C15—C161.518 (4)
C1—C61.417 (4)C15—H15A0.9700
C1—C101.427 (4)C15—H15B0.9700
C2—C31.377 (4)C16—C171.515 (4)
C2—H20.9300C16—H16A0.9700
C3—C41.390 (6)C16—H16B0.9700
C3—H30.9300C17—C181.514 (4)
C4—C51.344 (5)C17—H17A0.9700
C4—H40.9300C17—H17B0.9700
C5—C61.418 (5)C18—N11.459 (3)
C5—H50.9300C18—C191.516 (3)
C6—C71.416 (5)C18—H180.9800
C7—C81.341 (4)C19—C201.511 (3)
C7—H70.9300C19—H190.9800
C8—C91.399 (4)C20—C211.380 (3)
C8—H80.9300C20—C251.387 (4)
C9—C101.361 (4)C21—C221.385 (4)
C9—O11.374 (3)C21—H210.9300
C10—C111.521 (4)C22—C231.368 (4)
C11—N11.479 (3)C22—H220.9300
C11—C121.558 (3)C23—C241.379 (4)
C11—H110.9800C23—Br11.890 (3)
C12—C261.521 (4)C24—C251.383 (4)
C12—C131.521 (4)C24—H240.9300
C12—C191.574 (3)C25—H250.9300
C13—O11.435 (3)C26—O21.193 (3)
C13—H13A0.9700C26—O31.324 (3)
C13—H13B0.9700C27—O31.461 (4)
C14—N11.450 (3)C27—H27A0.9600
C14—C151.498 (4)C27—H27B0.9600
C14—H14A0.9700C27—H27C0.9600
C14—H14B0.9700
C2—C1—C6117.4 (3)C16—C15—H15B109.5
C2—C1—C10123.2 (3)H15A—C15—H15B108.1
C6—C1—C10119.4 (3)C17—C16—C15109.6 (2)
C3—C2—C1121.0 (3)C17—C16—H16A109.7
C3—C2—H2119.5C15—C16—H16A109.7
C1—C2—H2119.5C17—C16—H16B109.7
C2—C3—C4121.1 (4)C15—C16—H16B109.7
C2—C3—H3119.4H16A—C16—H16B108.2
C4—C3—H3119.4C18—C17—C16110.6 (2)
C5—C4—C3119.4 (4)C18—C17—H17A109.5
C5—C4—H4120.3C16—C17—H17A109.5
C3—C4—H4120.3C18—C17—H17B109.5
C4—C5—C6121.5 (4)C16—C17—H17B109.5
C4—C5—H5119.2H17A—C17—H17B108.1
C6—C5—H5119.2N1—C18—C17111.3 (2)
C7—C6—C1118.7 (3)N1—C18—C19100.2 (2)
C7—C6—C5121.8 (3)C17—C18—C19116.0 (2)
C1—C6—C5119.5 (4)N1—C18—H18109.6
C8—C7—C6120.8 (3)C17—C18—H18109.6
C8—C7—H7119.6C19—C18—H18109.6
C6—C7—H7119.6C20—C19—C18118.2 (2)
C7—C8—C9120.0 (3)C20—C19—C12115.9 (2)
C7—C8—H8120.0C18—C19—C12102.47 (19)
C9—C8—H8120.0C20—C19—H19106.5
C10—C9—O1121.1 (2)C18—C19—H19106.5
C10—C9—C8122.4 (3)C12—C19—H19106.5
O1—C9—C8116.5 (3)C21—C20—C25117.6 (2)
C9—C10—C1118.1 (3)C21—C20—C19119.6 (2)
C9—C10—C11119.7 (2)C25—C20—C19122.8 (2)
C1—C10—C11121.7 (3)C20—C21—C22121.8 (3)
N1—C11—C10112.9 (2)C20—C21—H21119.1
N1—C11—C12103.10 (19)C22—C21—H21119.1
C10—C11—C12112.9 (2)C23—C22—C21118.9 (3)
N1—C11—H11109.2C23—C22—H22120.6
C10—C11—H11109.2C21—C22—H22120.6
C12—C11—H11109.2C22—C23—C24121.4 (2)
C26—C12—C13111.0 (2)C22—C23—Br1119.3 (2)
C26—C12—C11110.4 (2)C24—C23—Br1119.3 (2)
C13—C12—C11110.9 (2)C23—C24—C25118.5 (3)
C26—C12—C19107.9 (2)C23—C24—H24120.7
C13—C12—C19112.5 (2)C25—C24—H24120.7
C11—C12—C19103.98 (19)C24—C25—C20121.8 (3)
O1—C13—C12111.4 (2)C24—C25—H25119.1
O1—C13—H13A109.3C20—C25—H25119.1
C12—C13—H13A109.3O2—C26—O3122.9 (3)
O1—C13—H13B109.3O2—C26—C12124.7 (3)
C12—C13—H13B109.3O3—C26—C12112.4 (3)
H13A—C13—H13B108.0O3—C27—H27A109.5
N1—C14—C15110.7 (2)O3—C27—H27B109.5
N1—C14—H14A109.5H27A—C27—H27B109.5
C15—C14—H14A109.5O3—C27—H27C109.5
N1—C14—H14B109.5H27A—C27—H27C109.5
C15—C14—H14B109.5H27B—C27—H27C109.5
H14A—C14—H14B108.1C14—N1—C18114.1 (2)
C14—C15—C16110.8 (2)C14—N1—C11118.1 (2)
C14—C15—H15A109.5C18—N1—C11106.10 (18)
C16—C15—H15A109.5C9—O1—C13112.0 (2)
C14—C15—H15B109.5C26—O3—C27113.0 (3)
C6—C1—C2—C3−1.2 (5)N1—C18—C19—C1242.9 (2)
C10—C1—C2—C3178.6 (3)C17—C18—C19—C12162.8 (2)
C1—C2—C3—C4−0.9 (6)C26—C12—C19—C2090.7 (3)
C2—C3—C4—C51.6 (6)C13—C12—C19—C20−32.0 (3)
C3—C4—C5—C6−0.1 (6)C11—C12—C19—C20−152.0 (2)
C2—C1—C6—C7−178.6 (3)C26—C12—C19—C18−139.1 (2)
C10—C1—C6—C71.6 (4)C13—C12—C19—C1898.1 (2)
C2—C1—C6—C52.5 (4)C11—C12—C19—C18−21.9 (2)
C10—C1—C6—C5−177.3 (3)C18—C19—C20—C21153.2 (2)
C4—C5—C6—C7179.2 (3)C12—C19—C20—C21−84.7 (3)
C4—C5—C6—C1−1.9 (5)C18—C19—C20—C25−27.3 (4)
C1—C6—C7—C84.1 (5)C12—C19—C20—C2594.9 (3)
C5—C6—C7—C8−177.0 (3)C25—C20—C21—C22−1.7 (4)
C6—C7—C8—C9−4.6 (5)C19—C20—C21—C22177.9 (3)
C7—C8—C9—C10−0.8 (4)C20—C21—C22—C230.8 (4)
C7—C8—C9—O1178.3 (3)C21—C22—C23—C241.3 (4)
O1—C9—C10—C1−172.6 (2)C21—C22—C23—Br1−177.7 (2)
C8—C9—C10—C16.5 (4)C22—C23—C24—C25−2.5 (4)
O1—C9—C10—C1115.6 (4)Br1—C23—C24—C25176.5 (2)
C8—C9—C10—C11−165.3 (2)C23—C24—C25—C201.6 (4)
C2—C1—C10—C9173.5 (3)C21—C20—C25—C240.4 (4)
C6—C1—C10—C9−6.7 (4)C19—C20—C25—C24−179.1 (2)
C2—C1—C10—C11−14.9 (4)C13—C12—C26—O2−159.1 (3)
C6—C1—C10—C11164.9 (3)C11—C12—C26—O2−35.8 (4)
C9—C10—C11—N189.9 (3)C19—C12—C26—O277.2 (3)
C1—C10—C11—N1−81.6 (3)C13—C12—C26—O322.0 (3)
C9—C10—C11—C12−26.5 (3)C11—C12—C26—O3145.3 (2)
C1—C10—C11—C12162.0 (2)C19—C12—C26—O3−101.6 (3)
N1—C11—C12—C26108.5 (2)C15—C14—N1—C18−55.9 (3)
C10—C11—C12—C26−129.3 (2)C15—C14—N1—C11178.3 (2)
N1—C11—C12—C13−128.1 (2)C17—C18—N1—C1454.8 (3)
C10—C11—C12—C13−6.0 (3)C19—C18—N1—C14178.1 (2)
N1—C11—C12—C19−7.0 (2)C17—C18—N1—C11−173.3 (2)
C10—C11—C12—C19115.1 (2)C19—C18—N1—C11−50.0 (2)
C26—C12—C13—O1172.0 (2)C10—C11—N1—C1442.9 (3)
C11—C12—C13—O148.9 (3)C12—C11—N1—C14165.0 (2)
C19—C12—C13—O1−67.0 (3)C10—C11—N1—C18−86.7 (2)
N1—C14—C15—C1656.3 (3)C12—C11—N1—C1835.5 (2)
C14—C15—C16—C17−56.7 (3)C10—C9—O1—C1330.1 (3)
C15—C16—C17—C1855.2 (3)C8—C9—O1—C13−149.1 (2)
C16—C17—C18—N1−53.9 (3)C12—C13—O1—C9−63.2 (3)
C16—C17—C18—C19−167.6 (2)O2—C26—O3—C271.2 (4)
N1—C18—C19—C20171.6 (2)C12—C26—O3—C27−180.0 (3)
C17—C18—C19—C20−68.5 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C15—H15B···Br1i0.972.733.588 (3)147

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2463).

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