4-(4-Bromo­phen­yl)-2,3,3a,4,5,11c-hexa­hydro­benzo[f]furo[3,2-c]quinoline

Wu, N.; Zhang, R.; Li, X.; Xu, X.; Xu, Z.

doi:10.1107/S1600536811031084

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2285

doi:10.1107/S1600536811031084

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4-(4-Bromophenyl)-2,3,3a,4,5,11c-hexahydrobenzo[f]furo[3,2-c]quinoline

Nan Wu,^a Rongli Zhang,^b Xinnian Li,^a Xin Xu ^a and Zhou Xu ^b ^*

^aDepartment of Aviation Oil and Materials, Xuzhou Airforce College, Xuzhou Jiangsu 221110, People's Republic of China, and ^bDepartment of Chemistry, Xuzhou Medical College, Xuzhou Jiangsu 221004, People's Republic of China
^*Correspondence e-mail: xuzhou@xzmc.edu.cn

(Received 14 April 2011; accepted 2 August 2011; online 11 August 2011)

In the title compound, C₂₁H₁₈BrNO, both heterocyclic rings, viz. the hydropyridine ring and the adjacent hydrofuran ring, adopt envelope conformations. These two heterocycles make a dihedral angle of 37.3 (1)°. The dihedral angle between the hydropyridine and benzene rings is 69.6 (1)°. In the crystal, adjacent molecules are linked by pairs of intermolecular 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_r = 380.27
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.033
wR(F²) = 0.076
S = 1.04
2921 reflections
221 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.32 e Å⁻³

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) -x+1, -y, -z+2.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811031084/zb2015sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811031084/zb2015Isup3.cml

checkCIF report

Comment top

Quinoline derivatives has been extensively studied due to its varies of biological properties, such as psychotropic activity (Nesterova, et al., 1995), anti-allergic (Yamada et al., 1992) and anti-inflammatory activity (Faber et al., 1984 and Johnson et al., 1989). The title compound (Fig. 1), may be used as a new precursor for obtaining bioactive molecules. Herein, we report the crystal structure of the title compound, (I).

In the crystal structure of (I), the hydropyridine ring of the furoquinoline moiety adopts an envelope conformation (Fig. 1). The atom C1 deviates from the plane defined by the atoms C2/C5/C6/C15/N1 by 0.646 (3) Å. This conformation is different from those reported in other hydropyridine derivatives (For related structrues, see Ramesh, et al., 2008; Zhao & Teng, 2008; Bai et al., 2009; Du, et al., 2010). In the adjacent hydrofuran ring, the atoms C2—C4 and O1 are coplanar, while the atom C5 deviates from the plane by 0.522 (3) Å. This data indicates that the above hydrofuran ring also adopts an envelope conformation. These two heterocycles make a dihedral angle of 37.3 (1)°. The basal plane of the hydropyridine ring is nearly coplanar to the naphthalene ring C6—C15, forming a dihedral angle of 6.0 (1)°. The dihedral angle between the phenyl and the hydropyridine ring is 69.6 (1)°. The hydrogen bond of C9—H9···O1 links the adjacent moleclues forming dimmers along a axis (Figure 2). This hydrogen bonding pattern is same with the one reported in literature (Wang et al., 2010).

Related literature top

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 top

The title compound, (I), was prepared by the reaction of 4-bromobenzaldehyde (0.361 g, 2.0 mmol), naphthalen-2-amine (0.286 g, 2.0 mmol), 2,3-dihydrofuran (0.252 g, 3.0 mmol), I₂ (0.026 g, 0.1 mmol) and THF (10 ml) for 18 h (yield 87%, mp. 523–525 K). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a DMF solution.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINTT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure drawing shows 30% probability of displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The molecular packing diagram of (I). Dashed lines indicate hydrogen bonds of type C9—H9···O1 which links the adjacent molecules forming dimmers along a.

4-(4-Bromophenyl)-2,3,3a,4,5,11c-hexahydrobenzo[f]furo[3,2- c]quinoline top

Crystal data top

C₂₁H₁₈BrNO	Z = 2
M_r = 380.27	F(000) = 388
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.033	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(F_o²) + (0.0327P)² + 0.242P] where P = (F_o² + 2F_c²)/3
2921 reflections	(Δ/σ)_max = 0.001
221 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₁H₁₈BrNO	γ = 92.469 (1)°
M_r = 380.27	V = 826.81 (3) Å³
Triclinic, P1	Z = 2
a = 9.4019 (2) Å	Mo Kα radiation
b = 9.6025 (2) Å	µ = 2.49 mm⁻¹
c = 10.4660 (2) Å	T = 296 K
α = 103.888 (1)°	0.20 × 0.09 × 0.04 mm
β = 114.075 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	2921 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2301 reflections with I > 2σ(I)
T_min = 0.793, T_max = 0.899	R_int = 0.037
10901 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.22 e Å⁻³
2921 reflections	Δρ_min = −0.32 e Å⁻³
221 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈BrNO
M_r	380.27
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.4019 (2), 9.6025 (2), 10.4660 (2)
α, β, γ (°)	103.888 (1), 114.075 (1), 92.469 (1)
V (Å³)	826.81 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.49
Crystal size (mm)	0.20 × 0.09 × 0.04

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.793, 0.899
No. of measured, independent and observed [I > 2σ(I)] reflections	10901, 2921, 2301
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.076, 1.04
No. of reflections	2921
No. of parameters	221
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.32

Computer programs: SMART (Bruker, 2001), SAINTT (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1ⁱ	0.93	2.69	3.462 (3)	141.0

Symmetry code: (i) −x+1, −y, −z+2.

Acknowledgements

We are grateful to the Special Presidential Foundation of Xuzhou Medical College (2010KJZ24) for financial support.

References

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