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

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ISSN: 2056-9890

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

aDepartment of Physics, AMET University, Kanathur, Chennai 603 112, India, bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
*Correspondence e-mail: manivan_1999@yahoo.com

(Received 18 September 2009; accepted 19 September 2009; online 26 September 2009)

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[Gundersen, L. L., Negussie, A. H., Rise, F. & Ostby, O. B. (2003). Arch. Pharm. (Weinheim), 336, 191-195.]); Teklu et al. (2005[Teklu, S., Gundersen, L. L., Larsen, T., Malterud, K. E. & Rise, F. (2005). Bioorg. Med. Chem. 13, 3127-3139.]); Foster et al. (1995[Foster, C., Ritchie, M., Selwood, D. I. & Snowden, W. (1995). Antivir. Chem. Chemother. 6, 289-297.]); Malonne et al. (1998[Malonne, H., Hanuise, J. & Fontaine, J. (1998). Pharm. Pharmacol. Commun. 4, 241-242.]); Medda et al. (2003[Medda, S., Jaisankar, P., Manna, R. K., Pal, B., Giri, V. S. & Basu, M. K. (2003). J. Drug Target, 11, 123-128.]). For related structures, see: Gunasekaran et al. (2009[Gunasekaran, B., Kathiravan, S., Raghunathan, R., Renuga, V. & Manivannan, V. (2009). Acta Cryst. E65, o1033.]); Kamala et al. (2009[Kamala, E. T. S., Nirmala, S., Sudha, L., Kathiravan, S. & Raghunathan, R. (2009). Acta Cryst. E65, o1923-o1924.]).

[Scheme 1]

Experimental

Crystal data
  • C27H26BrNO3

  • Mr = 492.40

  • Trigonal, [P \overline 3]

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.654, Tmax = 0.708

  • 23085 measured reflections

  • 5338 independent reflections

  • 2509 reflections with I > 2σ(I)

  • Rint = 0.113

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C15—H15B⋯Br1i 0.97 2.73 3.588 (3) 147
Symmetry code: (i) -x+y+1, -x+1, z-1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
Methyl 9-(4-bromophenyl)-8a,9,9a,10,11,12,13,14a-octahydro-8H- benzo[f]chromeno[3,4-b]indolizine-8a-carboxylate top
Crystal data top
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 top
Bruker Kappa APEXII CCD
diffractometer
5338 independent reflections
Radiation source: fine-focus sealed tube2509 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.113
Detector resolution: 0 pixels mm-1θmax = 27.8°, θmin = 2.2°
ω and ϕ scansh = 2224
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 2424
Tmin = 0.654, Tmax = 0.708l = 815
23085 measured reflections
Refinement top
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 = 0.85 w = 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
Crystal data top
C27H26BrNO3Z = 6
Mr = 492.40Mo Kα radiation
Trigonal, P3µ = 1.85 mm1
a = 18.4405 (8) ÅT = 293 K
c = 11.4828 (8) Å0.25 × 0.20 × 0.20 mm
V = 3381.6 (3) Å3
Data collection top
Bruker Kappa APEXII CCD
diffractometer
5338 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2509 reflections with I > 2σ(I)
Tmin = 0.654, Tmax = 0.708Rint = 0.113
23085 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0422 restraints
wR(F2) = 0.108H-atom parameters constrained
S = 0.85Δρmax = 0.85 e Å3
5338 reflectionsΔρmin = 0.33 e Å3
290 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
H20.24010.07690.30500.074*
C30.2515 (3)0.0339 (2)0.4604 (3)0.0850 (13)
H30.21230.04320.49820.102*
C40.2927 (3)0.0004 (2)0.5221 (3)0.0859 (13)
H40.28210.01150.60110.103*
C50.3479 (3)0.0149 (2)0.4667 (3)0.0786 (12)
H50.37520.03750.50820.094*
C60.3654 (2)0.00269 (18)0.3465 (3)0.0564 (9)
C70.4228 (2)0.01415 (18)0.2873 (3)0.0627 (10)
H70.45190.03490.32860.075*
C80.43567 (19)0.00053 (17)0.1725 (3)0.0513 (8)
H80.47040.01560.13360.062*
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)
H110.26690.10560.12420.041*
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*
H13B0.29200.01270.05310.052*
C140.41242 (18)0.23382 (17)0.2399 (2)0.0434 (7)
H14A0.36500.21800.29120.052*
H14B0.44160.20530.26630.052*
C150.47016 (18)0.32660 (18)0.2460 (2)0.0477 (8)
H15A0.43950.35500.22680.057*
H15B0.49140.34220.32470.057*
C160.54293 (18)0.35396 (18)0.1621 (3)0.0492 (8)
H16A0.57650.32930.18500.059*
H16B0.57820.41440.16440.059*
C170.50984 (18)0.32634 (16)0.0398 (2)0.0425 (7)
H17A0.55620.34040.01280.051*
H17B0.48150.35580.01400.051*
C180.44950 (16)0.23290 (15)0.0361 (2)0.0329 (6)
H180.47990.20290.05080.039*
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*
H27B0.12400.00910.28910.148*
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) top
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, º) top
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—C31.2 (5)N1—C18—C19—C1242.9 (2)
C10—C1—C2—C3178.6 (3)C17—C18—C19—C12162.8 (2)
C1—C2—C3—C40.9 (6)C26—C12—C19—C2090.7 (3)
C2—C3—C4—C51.6 (6)C13—C12—C19—C2032.0 (3)
C3—C4—C5—C60.1 (6)C11—C12—C19—C20152.0 (2)
C2—C1—C6—C7178.6 (3)C26—C12—C19—C18139.1 (2)
C10—C1—C6—C71.6 (4)C13—C12—C19—C1898.1 (2)
C2—C1—C6—C52.5 (4)C11—C12—C19—C1821.9 (2)
C10—C1—C6—C5177.3 (3)C18—C19—C20—C21153.2 (2)
C4—C5—C6—C7179.2 (3)C12—C19—C20—C2184.7 (3)
C4—C5—C6—C11.9 (5)C18—C19—C20—C2527.3 (4)
C1—C6—C7—C84.1 (5)C12—C19—C20—C2594.9 (3)
C5—C6—C7—C8177.0 (3)C25—C20—C21—C221.7 (4)
C6—C7—C8—C94.6 (5)C19—C20—C21—C22177.9 (3)
C7—C8—C9—C100.8 (4)C20—C21—C22—C230.8 (4)
C7—C8—C9—O1178.3 (3)C21—C22—C23—C241.3 (4)
O1—C9—C10—C1172.6 (2)C21—C22—C23—Br1177.7 (2)
C8—C9—C10—C16.5 (4)C22—C23—C24—C252.5 (4)
O1—C9—C10—C1115.6 (4)Br1—C23—C24—C25176.5 (2)
C8—C9—C10—C11165.3 (2)C23—C24—C25—C201.6 (4)
C2—C1—C10—C9173.5 (3)C21—C20—C25—C240.4 (4)
C6—C1—C10—C96.7 (4)C19—C20—C25—C24179.1 (2)
C2—C1—C10—C1114.9 (4)C13—C12—C26—O2159.1 (3)
C6—C1—C10—C11164.9 (3)C11—C12—C26—O235.8 (4)
C9—C10—C11—N189.9 (3)C19—C12—C26—O277.2 (3)
C1—C10—C11—N181.6 (3)C13—C12—C26—O322.0 (3)
C9—C10—C11—C1226.5 (3)C11—C12—C26—O3145.3 (2)
C1—C10—C11—C12162.0 (2)C19—C12—C26—O3101.6 (3)
N1—C11—C12—C26108.5 (2)C15—C14—N1—C1855.9 (3)
C10—C11—C12—C26129.3 (2)C15—C14—N1—C11178.3 (2)
N1—C11—C12—C13128.1 (2)C17—C18—N1—C1454.8 (3)
C10—C11—C12—C136.0 (3)C19—C18—N1—C14178.1 (2)
N1—C11—C12—C197.0 (2)C17—C18—N1—C11173.3 (2)
C10—C11—C12—C19115.1 (2)C19—C18—N1—C1150.0 (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—O167.0 (3)C10—C11—N1—C1886.7 (2)
N1—C14—C15—C1656.3 (3)C12—C11—N1—C1835.5 (2)
C14—C15—C16—C1756.7 (3)C10—C9—O1—C1330.1 (3)
C15—C16—C17—C1855.2 (3)C8—C9—O1—C13149.1 (2)
C16—C17—C18—N153.9 (3)C12—C13—O1—C963.2 (3)
C16—C17—C18—C19167.6 (2)O2—C26—O3—C271.2 (4)
N1—C18—C19—C20171.6 (2)C12—C26—O3—C27180.0 (3)
C17—C18—C19—C2068.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15B···Br1i0.972.733.588 (3)147
Symmetry code: (i) x+y+1, x+1, z1.

Experimental details

Crystal data
Chemical formulaC27H26BrNO3
Mr492.40
Crystal system, space groupTrigonal, P3
Temperature (K)293
a, c (Å)18.4405 (8), 11.4828 (8)
V3)3381.6 (3)
Z6
Radiation typeMo Kα
µ (mm1)1.85
Crystal size (mm)0.25 × 0.20 × 0.20
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.654, 0.708
No. of measured, independent and
observed [I > 2σ(I)] reflections
23085, 5338, 2509
Rint0.113
(sin θ/λ)max1)0.656
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.108, 0.85
No. of reflections5338
No. of parameters290
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.85, 0.33

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15B···Br1i0.972.733.588 (3)147
Symmetry code: (i) x+y+1, x+1, z1.
 

Acknowledgements

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

References

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