Methyl 9-(4-bromo-phen-yl)-8a,9,9a,10,11,12,13,14a-octa-hydro-8H-benzo[f]chromeno[3,4-b]indolizine-8a-car-box-ylate.

In the title compound, C(27)H(26)BrNO(3), 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 inter-molecular C-H⋯Br inter-action 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 = 492.40

Trigonal,

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 (; 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[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 ▶); 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.

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

C27H26BrNO3	Dx = 1.451 Mg m−3
Mr = 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

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

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(Fo2) + (0.0452P)2] where P = (Fo2 + 2Fc2)/3
5338 reflections	(Δ/σ)max < 0.001
290 parameters	Δρmax = 0.85 e Å−3
2 restraints	Δρmin = −0.33 e Å−3

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .