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

Gunasekaran, B.; Kathiravan, S.; Raghunathan, R.; Chakkaravarthi, G.; Manivannan, V.

doi:10.1107/S1600536809037994

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2550

doi:10.1107/S1600536809037994

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

B. Gunasekaran,^a S. Kathiravan,^b R. Raghunathan,^b G. Chakkaravarthi ^c and V. Manivannan ^d ^*

^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 ); 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

Crystal data

C₂₇H₂₆BrNO₃
M_r = 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 ) 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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.108
S = 0.85
5338 reflections
290 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037994/is2463sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037994/is2463Isup2.hkl

checkCIF report

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.

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

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

C₂₇H₂₆BrNO₃	D_x = 1.451 Mg m⁻³
M_r = 492.40	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3	Cell parameters from 4759 reflections
Hall symbol: -P 3	θ = 2.2–25.7°
a = 18.4405 (8) Å	µ = 1.85 mm⁻¹
c = 11.4828 (8) Å	T = 293 K
V = 3381.6 (3) Å³	Block, colourless
Z = 6	0.25 × 0.20 × 0.20 mm
F(000) = 1524

Data collection top

Bruker Kappa APEXII CCD diffractometer	5338 independent reflections
Radiation source: fine-focus sealed tube	2509 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.113
Detector resolution: 0 pixels mm^-1	θ_max = 27.8°, θ_min = 2.2°
ω and ϕ scans	h = −22→24
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −24→24
T_min = 0.654, T_max = 0.708	l = −8→15
23085 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 0.85	w = 1/[σ²(F_o²) + (0.0452P)²] where P = (F_o² + 2F_c²)/3
5338 reflections	(Δ/σ)_max < 0.001
290 parameters	Δρ_max = 0.85 e Å⁻³
2 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₇H₂₆BrNO₃	Z = 6
M_r = 492.40	Mo Kα radiation
Trigonal, P3	µ = 1.85 mm⁻¹
a = 18.4405 (8) Å	T = 293 K
c = 11.4828 (8) Å	0.25 × 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)
T_min = 0.654, T_max = 0.708	R_int = 0.113
23085 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	2 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 0.85	Δρ_max = 0.85 e Å⁻³
5338 reflections	Δρ_min = −0.33 e Å⁻³
290 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.32587 (18)	0.03952 (17)	−0.2836 (3)	0.0450 (7)
C2	0.2679 (2)	0.0537 (2)	−0.3441 (3)	0.0616 (9)
H2	0.2401	0.0769	−0.3050	0.074*
C3	0.2515 (3)	0.0339 (2)	−0.4604 (3)	0.0850 (13)
H3	0.2123	0.0432	−0.4982	0.102*
C4	0.2927 (3)	0.0004 (2)	−0.5221 (3)	0.0859 (13)
H4	0.2821	−0.0115	−0.6011	0.103*
C5	0.3479 (3)	−0.0149 (2)	−0.4667 (3)	0.0786 (12)
H5	0.3752	−0.0375	−0.5082	0.094*
C6	0.3654 (2)	0.00269 (18)	−0.3465 (3)	0.0564 (9)
C7	0.4228 (2)	−0.01415 (18)	−0.2873 (3)	0.0627 (10)
H7	0.4519	−0.0349	−0.3286	0.075*
C8	0.43567 (19)	−0.00053 (17)	−0.1725 (3)	0.0513 (8)
H8	0.4704	−0.0156	−0.1336	0.062*
C9	0.39688 (17)	0.03636 (16)	−0.1111 (2)	0.0384 (7)
C10	0.34630 (16)	0.06057 (15)	−0.1639 (2)	0.0356 (7)
C11	0.32309 (16)	0.11839 (16)	−0.1002 (2)	0.0341 (6)
H11	0.2669	0.1056	−0.1242	0.041*
C12	0.32533 (15)	0.11112 (16)	0.0348 (2)	0.0333 (6)
C13	0.34153 (18)	0.04079 (17)	0.0692 (2)	0.0431 (7)
H13A	0.3526	0.0438	0.1522	0.052*
H13B	0.2920	−0.0127	0.0531	0.052*
C14	0.41242 (18)	0.23382 (17)	−0.2399 (2)	0.0434 (7)
H14A	0.3650	0.2180	−0.2912	0.052*
H14B	0.4416	0.2053	−0.2663	0.052*
C15	0.47016 (18)	0.32660 (18)	−0.2460 (2)	0.0477 (8)
H15A	0.4395	0.3550	−0.2268	0.057*
H15B	0.4914	0.3422	−0.3247	0.057*
C16	0.54293 (18)	0.35396 (18)	−0.1621 (3)	0.0492 (8)
H16A	0.5765	0.3293	−0.1850	0.059*
H16B	0.5782	0.4144	−0.1644	0.059*
C17	0.50984 (18)	0.32634 (16)	−0.0398 (2)	0.0425 (7)
H17A	0.5562	0.3404	0.0128	0.051*
H17B	0.4815	0.3558	−0.0140	0.051*
C18	0.44950 (16)	0.23290 (15)	−0.0361 (2)	0.0329 (6)
H18	0.4799	0.2029	−0.0508	0.039*
C19	0.39796 (15)	0.19968 (16)	0.0742 (2)	0.0323 (6)
H19	0.3722	0.2342	0.0882	0.039*
C20	0.44263 (16)	0.20142 (16)	0.1853 (2)	0.0326 (6)
C21	0.40965 (17)	0.20588 (17)	0.2912 (2)	0.0395 (7)
H21	0.3612	0.2096	0.2925	0.047*
C22	0.44673 (19)	0.20491 (18)	0.3956 (2)	0.0454 (8)
H22	0.4232	0.2072	0.4662	0.054*
C23	0.51857 (18)	0.20047 (17)	0.3933 (2)	0.0414 (7)
C24	0.55532 (18)	0.19869 (17)	0.2895 (3)	0.0461 (8)
H24	0.6053	0.1979	0.2888	0.055*
C25	0.51612 (17)	0.19814 (17)	0.1866 (2)	0.0426 (7)
H25	0.5397	0.1955	0.1162	0.051*
C26	0.24417 (18)	0.09807 (19)	0.0883 (3)	0.0456 (7)
C27	0.1435 (2)	0.0356 (3)	0.2332 (4)	0.0985 (14)
H27A	0.1533	0.0860	0.2714	0.148*
H27B	0.1240	−0.0091	0.2891	0.148*
H27C	0.1021	0.0211	0.1735	0.148*
N1	0.38286 (13)	0.20806 (12)	−0.12185 (17)	0.0301 (5)
O1	0.41141 (11)	0.04609 (11)	0.00670 (17)	0.0446 (5)
O2	0.20524 (13)	0.12926 (15)	0.0531 (2)	0.0685 (7)
O3	0.22148 (12)	0.04877 (13)	0.18093 (17)	0.0569 (6)
Br1	0.56763 (2)	0.19502 (2)	0.53512 (3)	0.06620 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0421 (18)	0.0299 (16)	0.0472 (19)	0.0063 (14)	0.0072 (13)	−0.0069 (14)
C2	0.056 (2)	0.060 (2)	0.052 (2)	0.0171 (17)	−0.0091 (16)	−0.0117 (17)
C3	0.091 (3)	0.073 (3)	0.059 (3)	0.016 (2)	−0.019 (2)	−0.012 (2)
C4	0.116 (4)	0.060 (3)	0.052 (3)	0.021 (3)	0.002 (3)	−0.016 (2)
C5	0.110 (3)	0.042 (2)	0.061 (3)	0.022 (2)	0.020 (2)	−0.0113 (19)
C6	0.070 (2)	0.0282 (18)	0.053 (2)	0.0107 (17)	0.0124 (18)	−0.0059 (15)
C7	0.074 (3)	0.0336 (19)	0.077 (3)	0.0245 (19)	0.036 (2)	0.0021 (18)
C8	0.056 (2)	0.0335 (18)	0.068 (2)	0.0251 (16)	0.0165 (18)	0.0085 (16)
C9	0.0382 (17)	0.0246 (15)	0.0459 (19)	0.0109 (14)	0.0076 (14)	0.0020 (13)
C10	0.0324 (16)	0.0240 (15)	0.0413 (17)	0.0071 (13)	0.0047 (13)	−0.0016 (12)
C11	0.0281 (15)	0.0342 (16)	0.0382 (16)	0.0142 (13)	−0.0002 (12)	−0.0010 (13)
C12	0.0313 (16)	0.0295 (15)	0.0368 (16)	0.0134 (13)	0.0027 (12)	0.0023 (12)
C13	0.0474 (19)	0.0340 (17)	0.0440 (17)	0.0175 (15)	0.0040 (14)	0.0025 (13)
C14	0.0450 (18)	0.0462 (19)	0.0402 (17)	0.0236 (16)	0.0022 (14)	0.0055 (14)
C15	0.051 (2)	0.046 (2)	0.0464 (18)	0.0243 (16)	0.0104 (15)	0.0115 (15)
C16	0.0425 (18)	0.0320 (17)	0.069 (2)	0.0157 (15)	0.0108 (16)	0.0068 (15)
C17	0.0395 (18)	0.0322 (16)	0.0538 (19)	0.0165 (14)	−0.0031 (14)	−0.0018 (14)
C18	0.0354 (16)	0.0291 (15)	0.0369 (15)	0.0182 (13)	−0.0024 (13)	−0.0020 (12)
C19	0.0321 (16)	0.0315 (15)	0.0383 (16)	0.0197 (13)	−0.0019 (12)	−0.0035 (12)
C20	0.0346 (16)	0.0288 (15)	0.0370 (16)	0.0178 (13)	−0.0026 (12)	−0.0039 (12)
C21	0.0344 (16)	0.0452 (18)	0.0452 (18)	0.0246 (15)	−0.0037 (14)	−0.0045 (14)
C22	0.050 (2)	0.055 (2)	0.0356 (17)	0.0298 (17)	−0.0023 (14)	−0.0059 (14)
C23	0.0450 (19)	0.0389 (18)	0.0412 (18)	0.0217 (15)	−0.0112 (14)	0.0008 (13)
C24	0.0398 (18)	0.0508 (19)	0.056 (2)	0.0286 (16)	−0.0092 (15)	−0.0005 (15)
C25	0.0427 (18)	0.0492 (19)	0.0432 (18)	0.0285 (15)	−0.0001 (14)	−0.0020 (14)
C26	0.0377 (18)	0.0465 (19)	0.0462 (19)	0.0162 (14)	0.0011 (14)	−0.0031 (15)
C27	0.079 (3)	0.108 (3)	0.103 (3)	0.043 (3)	0.044 (2)	0.021 (3)
N1	0.0292 (12)	0.0280 (12)	0.0332 (12)	0.0143 (10)	0.0022 (10)	0.0007 (10)
O1	0.0462 (13)	0.0353 (12)	0.0571 (14)	0.0238 (10)	−0.0026 (10)	−0.0004 (10)
O2	0.0512 (15)	0.0940 (19)	0.0727 (16)	0.0455 (13)	0.0179 (12)	0.0238 (13)
O3	0.0493 (14)	0.0684 (15)	0.0484 (13)	0.0260 (12)	0.0151 (10)	0.0127 (11)
Br1	0.0694 (3)	0.0800 (3)	0.0538 (2)	0.0408 (2)	−0.01750 (18)	0.00658 (18)

Geometric parameters (Å, º) top

C1—C2	1.406 (4)	C15—C16	1.518 (4)
C1—C6	1.417 (4)	C15—H15A	0.9700
C1—C10	1.427 (4)	C15—H15B	0.9700
C2—C3	1.377 (4)	C16—C17	1.515 (4)
C2—H2	0.9300	C16—H16A	0.9700
C3—C4	1.390 (6)	C16—H16B	0.9700
C3—H3	0.9300	C17—C18	1.514 (4)
C4—C5	1.344 (5)	C17—H17A	0.9700
C4—H4	0.9300	C17—H17B	0.9700
C5—C6	1.418 (5)	C18—N1	1.459 (3)
C5—H5	0.9300	C18—C19	1.516 (3)
C6—C7	1.416 (5)	C18—H18	0.9800
C7—C8	1.341 (4)	C19—C20	1.511 (3)
C7—H7	0.9300	C19—H19	0.9800
C8—C9	1.399 (4)	C20—C21	1.380 (3)
C8—H8	0.9300	C20—C25	1.387 (4)
C9—C10	1.361 (4)	C21—C22	1.385 (4)
C9—O1	1.374 (3)	C21—H21	0.9300
C10—C11	1.521 (4)	C22—C23	1.368 (4)
C11—N1	1.479 (3)	C22—H22	0.9300
C11—C12	1.558 (3)	C23—C24	1.379 (4)
C11—H11	0.9800	C23—Br1	1.890 (3)
C12—C26	1.521 (4)	C24—C25	1.383 (4)
C12—C13	1.521 (4)	C24—H24	0.9300
C12—C19	1.574 (3)	C25—H25	0.9300
C13—O1	1.435 (3)	C26—O2	1.193 (3)
C13—H13A	0.9700	C26—O3	1.324 (3)
C13—H13B	0.9700	C27—O3	1.461 (4)
C14—N1	1.450 (3)	C27—H27A	0.9600
C14—C15	1.498 (4)	C27—H27B	0.9600
C14—H14A	0.9700	C27—H27C	0.9600
C14—H14B	0.9700

C2—C1—C6	117.4 (3)	C16—C15—H15B	109.5
C2—C1—C10	123.2 (3)	H15A—C15—H15B	108.1
C6—C1—C10	119.4 (3)	C17—C16—C15	109.6 (2)
C3—C2—C1	121.0 (3)	C17—C16—H16A	109.7
C3—C2—H2	119.5	C15—C16—H16A	109.7
C1—C2—H2	119.5	C17—C16—H16B	109.7
C2—C3—C4	121.1 (4)	C15—C16—H16B	109.7
C2—C3—H3	119.4	H16A—C16—H16B	108.2
C4—C3—H3	119.4	C18—C17—C16	110.6 (2)
C5—C4—C3	119.4 (4)	C18—C17—H17A	109.5
C5—C4—H4	120.3	C16—C17—H17A	109.5
C3—C4—H4	120.3	C18—C17—H17B	109.5
C4—C5—C6	121.5 (4)	C16—C17—H17B	109.5
C4—C5—H5	119.2	H17A—C17—H17B	108.1
C6—C5—H5	119.2	N1—C18—C17	111.3 (2)
C7—C6—C1	118.7 (3)	N1—C18—C19	100.2 (2)
C7—C6—C5	121.8 (3)	C17—C18—C19	116.0 (2)
C1—C6—C5	119.5 (4)	N1—C18—H18	109.6
C8—C7—C6	120.8 (3)	C17—C18—H18	109.6
C8—C7—H7	119.6	C19—C18—H18	109.6
C6—C7—H7	119.6	C20—C19—C18	118.2 (2)
C7—C8—C9	120.0 (3)	C20—C19—C12	115.9 (2)
C7—C8—H8	120.0	C18—C19—C12	102.47 (19)
C9—C8—H8	120.0	C20—C19—H19	106.5
C10—C9—O1	121.1 (2)	C18—C19—H19	106.5
C10—C9—C8	122.4 (3)	C12—C19—H19	106.5
O1—C9—C8	116.5 (3)	C21—C20—C25	117.6 (2)
C9—C10—C1	118.1 (3)	C21—C20—C19	119.6 (2)
C9—C10—C11	119.7 (2)	C25—C20—C19	122.8 (2)
C1—C10—C11	121.7 (3)	C20—C21—C22	121.8 (3)
N1—C11—C10	112.9 (2)	C20—C21—H21	119.1
N1—C11—C12	103.10 (19)	C22—C21—H21	119.1
C10—C11—C12	112.9 (2)	C23—C22—C21	118.9 (3)
N1—C11—H11	109.2	C23—C22—H22	120.6
C10—C11—H11	109.2	C21—C22—H22	120.6
C12—C11—H11	109.2	C22—C23—C24	121.4 (2)
C26—C12—C13	111.0 (2)	C22—C23—Br1	119.3 (2)
C26—C12—C11	110.4 (2)	C24—C23—Br1	119.3 (2)
C13—C12—C11	110.9 (2)	C23—C24—C25	118.5 (3)
C26—C12—C19	107.9 (2)	C23—C24—H24	120.7
C13—C12—C19	112.5 (2)	C25—C24—H24	120.7
C11—C12—C19	103.98 (19)	C24—C25—C20	121.8 (3)
O1—C13—C12	111.4 (2)	C24—C25—H25	119.1
O1—C13—H13A	109.3	C20—C25—H25	119.1
C12—C13—H13A	109.3	O2—C26—O3	122.9 (3)
O1—C13—H13B	109.3	O2—C26—C12	124.7 (3)
C12—C13—H13B	109.3	O3—C26—C12	112.4 (3)
H13A—C13—H13B	108.0	O3—C27—H27A	109.5
N1—C14—C15	110.7 (2)	O3—C27—H27B	109.5
N1—C14—H14A	109.5	H27A—C27—H27B	109.5
C15—C14—H14A	109.5	O3—C27—H27C	109.5
N1—C14—H14B	109.5	H27A—C27—H27C	109.5
C15—C14—H14B	109.5	H27B—C27—H27C	109.5
H14A—C14—H14B	108.1	C14—N1—C18	114.1 (2)
C14—C15—C16	110.8 (2)	C14—N1—C11	118.1 (2)
C14—C15—H15A	109.5	C18—N1—C11	106.10 (18)
C16—C15—H15A	109.5	C9—O1—C13	112.0 (2)
C14—C15—H15B	109.5	C26—O3—C27	113.0 (3)

C6—C1—C2—C3	−1.2 (5)	N1—C18—C19—C12	42.9 (2)
C10—C1—C2—C3	178.6 (3)	C17—C18—C19—C12	162.8 (2)
C1—C2—C3—C4	−0.9 (6)	C26—C12—C19—C20	90.7 (3)
C2—C3—C4—C5	1.6 (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—C7	1.6 (4)	C13—C12—C19—C18	98.1 (2)
C2—C1—C6—C5	2.5 (4)	C11—C12—C19—C18	−21.9 (2)
C10—C1—C6—C5	−177.3 (3)	C18—C19—C20—C21	153.2 (2)
C4—C5—C6—C7	179.2 (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—C8	4.1 (5)	C12—C19—C20—C25	94.9 (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—C22	177.9 (3)
C7—C8—C9—C10	−0.8 (4)	C20—C21—C22—C23	0.8 (4)
C7—C8—C9—O1	178.3 (3)	C21—C22—C23—C24	1.3 (4)
O1—C9—C10—C1	−172.6 (2)	C21—C22—C23—Br1	−177.7 (2)
C8—C9—C10—C1	6.5 (4)	C22—C23—C24—C25	−2.5 (4)
O1—C9—C10—C11	15.6 (4)	Br1—C23—C24—C25	176.5 (2)
C8—C9—C10—C11	−165.3 (2)	C23—C24—C25—C20	1.6 (4)
C2—C1—C10—C9	173.5 (3)	C21—C20—C25—C24	0.4 (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—C11	164.9 (3)	C11—C12—C26—O2	−35.8 (4)
C9—C10—C11—N1	89.9 (3)	C19—C12—C26—O2	77.2 (3)
C1—C10—C11—N1	−81.6 (3)	C13—C12—C26—O3	22.0 (3)
C9—C10—C11—C12	−26.5 (3)	C11—C12—C26—O3	145.3 (2)
C1—C10—C11—C12	162.0 (2)	C19—C12—C26—O3	−101.6 (3)
N1—C11—C12—C26	108.5 (2)	C15—C14—N1—C18	−55.9 (3)
C10—C11—C12—C26	−129.3 (2)	C15—C14—N1—C11	178.3 (2)
N1—C11—C12—C13	−128.1 (2)	C17—C18—N1—C14	54.8 (3)
C10—C11—C12—C13	−6.0 (3)	C19—C18—N1—C14	178.1 (2)
N1—C11—C12—C19	−7.0 (2)	C17—C18—N1—C11	−173.3 (2)
C10—C11—C12—C19	115.1 (2)	C19—C18—N1—C11	−50.0 (2)
C26—C12—C13—O1	172.0 (2)	C10—C11—N1—C14	42.9 (3)
C11—C12—C13—O1	48.9 (3)	C12—C11—N1—C14	165.0 (2)
C19—C12—C13—O1	−67.0 (3)	C10—C11—N1—C18	−86.7 (2)
N1—C14—C15—C16	56.3 (3)	C12—C11—N1—C18	35.5 (2)
C14—C15—C16—C17	−56.7 (3)	C10—C9—O1—C13	30.1 (3)
C15—C16—C17—C18	55.2 (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—C27	1.2 (4)
N1—C18—C19—C20	171.6 (2)	C12—C26—O3—C27	−180.0 (3)
C17—C18—C19—C20	−68.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···Br1ⁱ	0.97	2.73	3.588 (3)	147

Symmetry code: (i) −x+y+1, −x+1, z−1.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₆BrNO₃
M_r	492.40
Crystal system, space group	Trigonal, P3
Temperature (K)	293
a, c (Å)	18.4405 (8), 11.4828 (8)
V (Å³)	3381.6 (3)
Z	6
Radiation type	Mo Kα
µ (mm⁻¹)	1.85
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.654, 0.708
No. of measured, independent and observed [I > 2σ(I)] reflections	23085, 5338, 2509
R_int	0.113
(sin θ/λ)_max (Å⁻¹)	0.656

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.108, 0.85
No. of reflections	5338
No. of parameters	290
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
C15—H15B···Br1ⁱ	0.97	2.73	3.588 (3)	147

Symmetry code: (i) −x+y+1, −x+1, z−1.

Acknowledgements

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

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Foster, C., Ritchie, M., Selwood, D. I. & Snowden, W. (1995). Antivir. Chem. Chemother. 6, 289–297. CAS Google Scholar
Gunasekaran, B., Kathiravan, S., Raghunathan, R., Renuga, V. & Manivannan, V. (2009). Acta Cryst. E65, o1033. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gundersen, L. L., Negussie, A. H., Rise, F. & Ostby, O. B. (2003). Arch. Pharm. (Weinheim), 336, 191–195. Web of Science CrossRef PubMed CAS Google Scholar
Kamala, E. T. S., Nirmala, S., Sudha, L., Kathiravan, S. & Raghunathan, R. (2009). Acta Cryst. E65, o1923–o1924. Web of Science CSD CrossRef IUCr Journals Google Scholar
Malonne, H., Hanuise, J. & Fontaine, J. (1998). Pharm. Pharmacol. Commun. 4, 241–242. CAS Google Scholar
Medda, S., Jaisankar, P., Manna, R. K., Pal, B., Giri, V. S. & Basu, M. K. (2003). J. Drug Target, 11, 123–128. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. 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
Teklu, S., Gundersen, L. L., Larsen, T., Malterud, K. E. & Rise, F. (2005). Bioorg. Med. Chem. 13, 3127–3139. Web of Science CrossRef PubMed CAS Google Scholar

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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