4-(4-Bromo-phen-yl)-2,3,3a,4,5,11c-hexa-hydro-benzo[f]furo[3,2-c]quinoline.

In the title compound, C(21)H(18)BrNO, both heterocyclic rings, viz. the hydro-pyridine ring and the adjacent hydro-furan ring, adopt envelope conformations. These two heterocycles make a dihedral angle of 37.3 (1)°. The dihedral angle between the hydro-pyridine and benzene rings is 69.6 (1)°. In the crystal, adjacent mol-ecules are linked by pairs of inter-molecular C-H⋯O hydrogen bonds, forming centrosymmetric dimers.

Related literature

For the biological properties of quinoline derivatives, see: Nesterova et al. (1995 ▶); Yamada et al. (1992 ▶); Faber et al. (1984 ▶); Johnson et al. (1989 ▶). For related structures, see: Ramesh et al. (2008 ▶); Zhao & Teng (2008 ▶); Bai et al. (2009 ▶); Du et al. (2010 ▶); Wang et al. (2010 ▶).

Experimental

Crystal data

C21H18BrNO

M = 380.27

Triclinic,

a = 9.4019 (2) Å

b = 9.6025 (2) Å

c = 10.4660 (2) Å

α = 103.888 (1)°

β = 114.075 (1)°

γ = 92.469 (1)°

V = 826.81 (3) Å3

Z = 2

Mo Kα radiation

μ = 2.49 mm−1

T = 296 K

0.20 × 0.09 × 0.04 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.793, T max = 0.899

10901 measured reflections

2921 independent reflections

2301 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.076

S = 1.04

2921 reflections

221 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031084/zb2015sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031084/zb2015Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811031084/zb2015Isup3.cml

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

C21H18BrNO	Z = 2
Mr = 380.27	F(000) = 388
Triclinic, P1	Dx = 1.527 Mg m−3
Hall symbol: -P 1	Melting point = 523–525 K
a = 9.4019 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.6025 (2) Å	Cell parameters from 2885 reflections
c = 10.4660 (2) Å	θ = 2.2–22.9°
α = 103.888 (1)°	µ = 2.49 mm−1
β = 114.075 (1)°	T = 296 K
γ = 92.469 (1)°	Block, colourless
V = 826.81 (3) Å3	0.20 × 0.09 × 0.04 mm

Bruker APEXII area-detector diffractometer	2921 independent reflections
Radiation source: fine-focus sealed tube	2301 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
Tmin = 0.793, Tmax = 0.899	k = −11→11
10901 measured reflections	l = −12→12

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0327P)2 + 0.242P] where P = (Fo2 + 2Fc2)/3
2921 reflections	(Δ/σ)max = 0.001
221 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	1.51042 (4)	0.37481 (4)	0.64000 (4)	0.05334 (14)
O1	0.7657 (2)	0.0345 (2)	0.8561 (2)	0.0463 (5)
C16	1.1935 (3)	0.2498 (3)	0.8548 (3)	0.0360 (6)
C19	1.3806 (3)	0.3222 (3)	0.7264 (3)	0.0364 (6)
N1	1.1406 (3)	0.3070 (3)	1.0684 (3)	0.0457 (7)
C6	0.8940 (3)	0.2371 (3)	1.0725 (3)	0.0335 (6)
C1	1.0888 (3)	0.2098 (3)	0.9222 (3)	0.0387 (7)
H1B	1.0959	0.1099	0.9283	0.046*
C21	1.2412 (3)	0.1435 (3)	0.7724 (3)	0.0430 (7)
H21	1.2100	0.0462	0.7605	0.052*
C12	0.8804 (3)	0.2858 (3)	1.3089 (3)	0.0387 (7)
C20	1.3343 (3)	0.1788 (3)	0.7073 (3)	0.0446 (7)
H20	1.3647	0.1063	0.6515	0.054*
C15	1.0518 (3)	0.2965 (3)	1.1442 (3)	0.0377 (7)
C7	0.8052 (3)	0.2325 (3)	1.1546 (3)	0.0330 (6)
C5	0.8148 (3)	0.1891 (3)	0.9095 (3)	0.0350 (6)
H5	0.7211	0.2361	0.8765	0.042*
C2	0.9162 (3)	0.2214 (3)	0.8341 (3)	0.0400 (7)
H2	0.9075	0.3181	0.8190	0.048*
C17	1.2421 (3)	0.3929 (3)	0.8702 (3)	0.0480 (8)
H17	1.2106	0.4661	0.9242	0.058*
C8	0.6415 (3)	0.1764 (3)	1.0879 (3)	0.0383 (7)
H8	0.5893	0.1401	0.9869	0.046*
C9	0.5593 (3)	0.1746 (3)	1.1694 (3)	0.0434 (7)
H9	0.4519	0.1385	1.1231	0.052*
C11	0.7913 (4)	0.2808 (3)	1.3891 (3)	0.0478 (8)
H11	0.8407	0.3153	1.4903	0.057*
C10	0.6344 (4)	0.2263 (3)	1.3208 (3)	0.0491 (8)
H10	0.5776	0.2237	1.3753	0.059*
C14	1.1242 (3)	0.3524 (3)	1.2979 (3)	0.0473 (8)
H14	1.2300	0.3943	1.3452	0.057*
C18	1.3365 (3)	0.4302 (3)	0.8073 (3)	0.0453 (7)
H18	1.3695	0.5273	0.8199	0.054*
C13	1.0424 (4)	0.3462 (3)	1.3777 (3)	0.0471 (8)
H13	1.0932	0.3820	1.4788	0.057*
C3	0.8387 (4)	0.1035 (4)	0.6873 (3)	0.0576 (9)
H3A	0.7779	0.1450	0.6097	0.069*
H3B	0.9180	0.0569	0.6639	0.069*
C4	0.7334 (4)	−0.0034 (4)	0.7062 (3)	0.0610 (9)
H4A	0.6236	0.0002	0.6472	0.073*
H4B	0.7538	−0.1011	0.6758	0.073*
H1A	1.234 (4)	0.323 (3)	1.114 (3)	0.052 (10)*

	U11	U22	U33	U12	U13	U23
Br1	0.0485 (2)	0.0682 (2)	0.0570 (2)	0.00705 (16)	0.03258 (16)	0.02427 (18)
O1	0.0560 (12)	0.0410 (12)	0.0405 (12)	−0.0063 (10)	0.0247 (10)	0.0045 (10)
N1	0.0306 (14)	0.0645 (18)	0.0388 (15)	−0.0024 (13)	0.0144 (12)	0.0120 (14)
C1	0.0387 (16)	0.0397 (16)	0.0401 (17)	0.0031 (13)	0.0190 (14)	0.0126 (14)
C2	0.0389 (16)	0.0452 (17)	0.0399 (17)	0.0026 (13)	0.0179 (13)	0.0182 (15)
C3	0.0471 (18)	0.083 (3)	0.0358 (18)	−0.0093 (17)	0.0177 (15)	0.0092 (18)
C4	0.082 (2)	0.053 (2)	0.046 (2)	−0.0024 (18)	0.0342 (18)	0.0023 (17)
C5	0.0334 (15)	0.0381 (16)	0.0351 (16)	0.0025 (12)	0.0156 (12)	0.0122 (14)
C6	0.0351 (15)	0.0335 (15)	0.0318 (15)	0.0037 (12)	0.0141 (12)	0.0099 (13)
C7	0.0399 (15)	0.0264 (14)	0.0353 (15)	0.0054 (12)	0.0186 (13)	0.0089 (13)
C8	0.0417 (16)	0.0342 (16)	0.0405 (17)	0.0027 (13)	0.0202 (13)	0.0093 (14)
C9	0.0457 (17)	0.0352 (16)	0.057 (2)	0.0028 (13)	0.0314 (16)	0.0097 (15)
C10	0.066 (2)	0.0423 (18)	0.055 (2)	0.0022 (16)	0.0432 (18)	0.0111 (16)
C11	0.068 (2)	0.0406 (18)	0.0398 (18)	0.0021 (16)	0.0305 (17)	0.0085 (15)
C12	0.0494 (17)	0.0340 (16)	0.0348 (16)	0.0040 (13)	0.0200 (14)	0.0105 (14)
C13	0.0525 (19)	0.0485 (19)	0.0331 (16)	0.0013 (15)	0.0138 (15)	0.0084 (15)
C14	0.0383 (17)	0.0534 (19)	0.0400 (18)	−0.0042 (14)	0.0112 (14)	0.0074 (16)
C15	0.0348 (15)	0.0414 (17)	0.0380 (16)	0.0038 (13)	0.0162 (13)	0.0126 (14)
C16	0.0328 (15)	0.0365 (16)	0.0410 (17)	0.0043 (12)	0.0169 (13)	0.0134 (14)
C17	0.059 (2)	0.0356 (17)	0.063 (2)	0.0094 (15)	0.0400 (17)	0.0116 (16)
C18	0.0505 (18)	0.0342 (16)	0.059 (2)	0.0015 (14)	0.0324 (16)	0.0116 (16)
C19	0.0318 (14)	0.0437 (17)	0.0367 (16)	0.0046 (13)	0.0162 (13)	0.0141 (14)
C20	0.0472 (17)	0.0413 (18)	0.0517 (19)	0.0104 (14)	0.0297 (15)	0.0087 (15)
C21	0.0442 (17)	0.0337 (16)	0.0562 (19)	0.0061 (13)	0.0255 (15)	0.0146 (15)

Br1—C19	1.905 (3)	C7—C8	1.420 (4)
O1—C4	1.420 (3)	C5—C2	1.527 (3)
O1—C5	1.436 (3)	C5—H5	0.9800
C16—C17	1.379 (4)	C2—C3	1.534 (4)
C16—C21	1.386 (4)	C2—H2	0.9800
C16—C1	1.510 (3)	C17—C18	1.383 (4)
C19—C18	1.366 (4)	C17—H17	0.9300
C19—C20	1.368 (4)	C8—C9	1.367 (4)
N1—C15	1.381 (3)	C8—H8	0.9300
N1—C1	1.454 (4)	C9—C10	1.391 (4)
N1—H1A	0.80 (3)	C9—H9	0.9300
C6—C15	1.379 (4)	C11—C10	1.362 (4)
C6—C7	1.428 (3)	C11—H11	0.9300
C6—C5	1.494 (4)	C10—H10	0.9300
C1—C2	1.529 (4)	C14—C13	1.355 (4)
C1—H1B	0.9800	C14—H14	0.9300
C21—C20	1.384 (4)	C18—H18	0.9300
C21—H21	0.9300	C13—H13	0.9300
C12—C11	1.414 (4)	C3—C4	1.497 (4)
C12—C13	1.415 (4)	C3—H3A	0.9700
C12—C7	1.417 (4)	C3—H3B	0.9700
C20—H20	0.9300	C4—H4A	0.9700
C15—C14	1.415 (4)	C4—H4B	0.9700
C4—O1—C5	105.9 (2)	C5—C2—C3	102.0 (2)
C17—C16—C21	117.7 (2)	C1—C2—C3	112.5 (2)
C17—C16—C1	121.3 (2)	C5—C2—H2	110.3
C21—C16—C1	121.0 (2)	C1—C2—H2	110.3
C18—C19—C20	121.5 (2)	C3—C2—H2	110.3
C18—C19—Br1	118.6 (2)	C16—C17—C18	121.6 (3)
C20—C19—Br1	119.9 (2)	C16—C17—H17	119.2
C15—N1—C1	118.9 (2)	C18—C17—H17	119.2
C15—N1—H1A	117 (2)	C9—C8—C7	121.3 (3)
C1—N1—H1A	113 (2)	C9—C8—H8	119.4
C15—C6—C7	119.5 (2)	C7—C8—H8	119.4
C15—C6—C5	119.7 (2)	C8—C9—C10	120.7 (3)
C7—C6—C5	120.6 (2)	C8—C9—H9	119.6
N1—C1—C16	109.9 (2)	C10—C9—H9	119.6
N1—C1—C2	107.6 (2)	C10—C11—C12	121.2 (3)
C16—C1—C2	112.3 (2)	C10—C11—H11	119.4
N1—C1—H1B	109.0	C12—C11—H11	119.4
C16—C1—H1B	109.0	C11—C10—C9	119.9 (3)
C2—C1—H1B	109.0	C11—C10—H10	120.1
C20—C21—C16	121.5 (3)	C9—C10—H10	120.1
C20—C21—H21	119.3	C13—C14—C15	121.3 (3)
C16—C21—H21	119.3	C13—C14—H14	119.3
C11—C12—C13	122.0 (3)	C15—C14—H14	119.3
C11—C12—C7	119.4 (3)	C19—C18—C17	118.9 (3)
C13—C12—C7	118.6 (3)	C19—C18—H18	120.5
C19—C20—C21	118.8 (3)	C17—C18—H18	120.5
C19—C20—H20	120.6	C14—C13—C12	120.7 (3)
C21—C20—H20	120.6	C14—C13—H13	119.6
C6—C15—N1	121.3 (3)	C12—C13—H13	119.6
C6—C15—C14	119.9 (3)	C4—C3—C2	105.5 (2)
N1—C15—C14	118.8 (2)	C4—C3—H3A	110.6
C12—C7—C8	117.5 (2)	C2—C3—H3A	110.6
C12—C7—C6	119.9 (2)	C4—C3—H3B	110.6
C8—C7—C6	122.6 (2)	C2—C3—H3B	110.6
O1—C5—C6	110.8 (2)	H3A—C3—H3B	108.8
O1—C5—C2	104.9 (2)	O1—C4—C3	107.6 (3)
C6—C5—C2	115.6 (2)	O1—C4—H4A	110.2
O1—C5—H5	108.4	C3—C4—H4A	110.2
C6—C5—H5	108.4	O1—C4—H4B	110.2
C2—C5—H5	108.4	C3—C4—H4B	110.2
C5—C2—C1	111.1 (2)	H4A—C4—H4B	108.5
C15—N1—C1—C16	174.5 (2)	C7—C6—C5—C2	170.7 (2)
C15—N1—C1—C2	52.0 (3)	O1—C5—C2—C1	−88.2 (3)
C17—C16—C1—N1	−41.8 (3)	C6—C5—C2—C1	34.2 (3)
C21—C16—C1—N1	139.6 (3)	O1—C5—C2—C3	31.8 (3)
C17—C16—C1—C2	77.9 (3)	C6—C5—C2—C3	154.2 (2)
C21—C16—C1—C2	−100.6 (3)	N1—C1—C2—C5	−55.6 (3)
C17—C16—C21—C20	−0.1 (4)	C16—C1—C2—C5	−176.6 (2)
C1—C16—C21—C20	178.5 (3)	N1—C1—C2—C3	−169.2 (2)
C18—C19—C20—C21	−0.3 (4)	C16—C1—C2—C3	69.7 (3)
Br1—C19—C20—C21	179.4 (2)	C21—C16—C17—C18	−0.6 (4)
C16—C21—C20—C19	0.6 (4)	C1—C16—C17—C18	−179.2 (3)
C7—C6—C15—N1	−178.0 (2)	C12—C7—C8—C9	0.4 (4)
C5—C6—C15—N1	−2.8 (4)	C6—C7—C8—C9	−179.4 (2)
C7—C6—C15—C14	−0.1 (4)	C7—C8—C9—C10	−0.9 (4)
C5—C6—C15—C14	175.1 (2)	C13—C12—C11—C10	178.0 (3)
C1—N1—C15—C6	−23.0 (4)	C7—C12—C11—C10	−0.3 (4)
C1—N1—C15—C14	159.1 (3)	C12—C11—C10—C9	−0.1 (4)
C11—C12—C7—C8	0.2 (4)	C8—C9—C10—C11	0.7 (4)
C13—C12—C7—C8	−178.2 (2)	C6—C15—C14—C13	1.5 (4)
C11—C12—C7—C6	−180.0 (2)	N1—C15—C14—C13	179.4 (3)
C13—C12—C7—C6	1.6 (4)	C20—C19—C18—C17	−0.4 (4)
C15—C6—C7—C12	−1.4 (4)	Br1—C19—C18—C17	179.9 (2)
C5—C6—C7—C12	−176.5 (2)	C16—C17—C18—C19	0.9 (4)
C15—C6—C7—C8	178.4 (2)	C15—C14—C13—C12	−1.3 (4)
C5—C6—C7—C8	3.3 (4)	C11—C12—C13—C14	−178.6 (3)
C4—O1—C5—C6	−164.3 (2)	C7—C12—C13—C14	−0.3 (4)
C4—O1—C5—C2	−38.9 (3)	C5—C2—C3—C4	−13.9 (3)
C15—C6—C5—O1	114.7 (3)	C1—C2—C3—C4	105.2 (3)
C7—C6—C5—O1	−70.2 (3)	C5—O1—C4—C3	29.8 (3)
C15—C6—C5—C2	−4.4 (4)	C2—C3—C4—O1	−8.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1i	0.93	2.69	3.462 (3)	141.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1i	0.93	2.69	3.462 (3)	141

Symmetry code: (i) .