2-(4-Bromo-phen-yl)-4-(4-meth-oxy-phen-yl)-6,7,8,9-tetra-hydro-5H-cyclo-hepta-[b]pyridine.

In the title compound, C23H22BrNO, the cyclo-heptane ring adopts a chair conformation. The pyridine ring makes dihedral angles of 58.63 (15) and 8.27 (16)° with the benzene rings. The dihedral angle between the benzene rings is 56.68 (17)°. The crystal packing features C-Br⋯π inter-actions [Br⋯centroid distances= 3.813 (2) and 3.839 (2) Å; C-Br⋯centroid = 126.25 (10) and 138.31 (10)°, respectively, forming a three dimensional supramolecular architecture.

Related literature

For the biological and pharmacological properties of pyridine-based heterocycles, see: Aida et al. (2009 ▶); Ceylan & Gezegen (2008 ▶); Cundy et al. (1997 ▶); El-borai et al. (2012 ▶); Gezegen et al. (2010 ▶); Girgis et al. (2007 ▶); Hatanaka et al. (2005 ▶); Khidre et al. (2011 ▶); Laine-Cessac et al. (1997 ▶); Menegatti et al. (2006 ▶); Musiol et al. (2007 ▶); Rajanarendar et al. (2012 ▶). For ring conformation analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C23H22BrNO

M = 408.32

Monoclinic,

a = 10.409 (5) Å

b = 10.054 (5) Å

c = 18.428 (5) Å

β = 94.850 (5)°

V = 1921.6 (14) Å3

Z = 4

Mo Kα radiation

μ = 2.15 mm−1

T = 296 K

0.58 × 0.42 × 0.26 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.355, T max = 0.572

28207 measured reflections

3986 independent reflections

3083 reflections with I > 2σ(I)

R int = 0.178

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.119

S = 1.12

3986 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.42 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813013913/rz5059sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013913/rz5059Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013913/rz5059Isup3.cml

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

C23H22BrNO	F(000) = 840
Mr = 408.32	Dx = 1.411 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3507 reflections
a = 10.409 (5) Å	θ = 2.0–29.7°
b = 10.054 (5) Å	µ = 2.15 mm−1
c = 18.428 (5) Å	T = 296 K
β = 94.850 (5)°	Prism, yellow
V = 1921.6 (14) Å3	0.58 × 0.42 × 0.26 mm
Z = 4

Stoe IPDS 2 diffractometer	3986 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3083 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.178
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.0°
ω scans	h = −13→13
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
Tmin = 0.355, Tmax = 0.572	l = −23→23
28207 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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0476P)2 + 0.6943P] where P = (Fo2 + 2Fc2)/3
3986 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.67 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.22100 (4)	0.14765 (5)	0.68332 (2)	0.0767 (1)
O1	−0.3941 (2)	0.0596 (2)	0.06337 (14)	0.0741 (9)
N1	0.3068 (2)	0.0105 (3)	0.32719 (14)	0.0564 (9)
C1	0.1937 (3)	0.0478 (3)	0.35239 (16)	0.0532 (10)
C2	0.0825 (3)	0.0575 (3)	0.30651 (17)	0.0562 (10)
C3	0.0829 (3)	0.0282 (3)	0.23272 (17)	0.0544 (10)
C4	0.2004 (3)	−0.0098 (3)	0.20640 (17)	0.0553 (10)
C5	0.3082 (3)	−0.0176 (3)	0.25619 (17)	0.0568 (10)
C6	0.4390 (3)	−0.0579 (4)	0.2335 (2)	0.0700 (12)
C7	0.4441 (4)	−0.1991 (4)	0.2031 (2)	0.0798 (16)
C8	0.3898 (4)	−0.2128 (5)	0.1245 (2)	0.0865 (17)
C9	0.2484 (4)	−0.1809 (4)	0.1093 (2)	0.0839 (16)
C10	0.2126 (4)	−0.0375 (4)	0.12674 (19)	0.0721 (14)
C11	−0.0402 (3)	0.0400 (3)	0.18588 (16)	0.0551 (10)
C12	−0.1082 (3)	0.1580 (3)	0.18180 (18)	0.0595 (11)
C13	−0.2265 (3)	0.1698 (3)	0.14134 (18)	0.0601 (11)
C14	−0.2783 (3)	0.0606 (3)	0.10434 (17)	0.0586 (11)
C15	−0.2119 (4)	−0.0577 (4)	0.1079 (2)	0.0728 (12)
C16	−0.0948 (4)	−0.0675 (4)	0.1480 (2)	0.0691 (11)
C17	−0.4694 (4)	0.1773 (4)	0.0621 (2)	0.0760 (14)
C18	0.1993 (3)	0.0751 (3)	0.43212 (16)	0.0505 (9)
C19	0.3097 (3)	0.0476 (4)	0.47628 (18)	0.0647 (11)
C20	0.3172 (3)	0.0689 (4)	0.55055 (19)	0.0641 (11)
C21	0.2123 (3)	0.1207 (3)	0.58153 (17)	0.0562 (10)
C22	0.1016 (3)	0.1529 (4)	0.53894 (18)	0.0658 (11)
C23	0.0957 (3)	0.1291 (3)	0.46491 (18)	0.0624 (11)
H2	0.00620	0.08400	0.32510	0.0670*
H6A	0.50170	−0.05060	0.27530	0.0830*
H6B	0.46390	0.00400	0.19690	0.0830*
H7A	0.53320	−0.22860	0.20700	0.0960*
H7B	0.39660	−0.25760	0.23300	0.0960*
H8A	0.43830	−0.15480	0.09480	0.1040*
H8B	0.40390	−0.30340	0.10890	0.1040*
H9A	0.19910	−0.24060	0.13770	0.1000*
H9B	0.22330	−0.19800	0.05820	0.1000*
H10A	0.27760	0.02140	0.10980	0.0870*
H10B	0.13120	−0.01610	0.09960	0.0870*
H12	−0.07370	0.23180	0.20690	0.0710*
H13	−0.27030	0.25050	0.13930	0.0720*
H15	−0.24640	−0.13170	0.08300	0.0870*
H16	−0.05130	−0.14840	0.14970	0.0830*
H17A	−0.54790	0.16370	0.03180	0.1140*
H17B	−0.42180	0.24920	0.04290	0.1140*
H17C	−0.48930	0.19860	0.11060	0.1140*
H19	0.38120	0.01360	0.45550	0.0780*
H20	0.39230	0.04840	0.57930	0.0770*
H22	0.03170	0.19020	0.55980	0.0790*
H23	0.02040	0.14980	0.43630	0.0750*

	U11	U22	U33	U12	U13	U23
Br1	0.0721 (2)	0.1010 (3)	0.0569 (2)	0.0059 (2)	0.0055 (2)	−0.0121 (2)
O1	0.0727 (15)	0.0659 (15)	0.0804 (16)	0.0092 (12)	−0.0131 (12)	−0.0115 (12)
N1	0.0601 (16)	0.0502 (14)	0.0594 (15)	0.0013 (12)	0.0077 (12)	−0.0005 (12)
C1	0.0608 (18)	0.0430 (16)	0.0564 (16)	0.0004 (14)	0.0080 (14)	0.0016 (13)
C2	0.0578 (17)	0.0502 (18)	0.0613 (17)	0.0005 (14)	0.0096 (14)	−0.0026 (14)
C3	0.0634 (18)	0.0427 (16)	0.0570 (17)	−0.0029 (14)	0.0039 (14)	0.0017 (13)
C4	0.0655 (19)	0.0487 (17)	0.0528 (16)	−0.0003 (14)	0.0115 (14)	0.0005 (13)
C5	0.0653 (18)	0.0504 (18)	0.0557 (17)	0.0000 (15)	0.0119 (14)	−0.0012 (14)
C6	0.065 (2)	0.081 (2)	0.065 (2)	0.0042 (19)	0.0118 (16)	−0.0063 (18)
C7	0.083 (3)	0.082 (3)	0.076 (2)	0.019 (2)	0.017 (2)	−0.005 (2)
C8	0.094 (3)	0.085 (3)	0.083 (3)	0.008 (2)	0.022 (2)	−0.024 (2)
C9	0.089 (3)	0.090 (3)	0.074 (2)	−0.008 (2)	0.015 (2)	−0.023 (2)
C10	0.073 (2)	0.085 (3)	0.0592 (19)	−0.001 (2)	0.0102 (16)	−0.0013 (18)
C11	0.0635 (18)	0.0493 (18)	0.0532 (16)	−0.0004 (15)	0.0089 (14)	−0.0016 (13)
C12	0.0670 (19)	0.0494 (18)	0.0622 (18)	−0.0037 (15)	0.0066 (15)	−0.0081 (14)
C13	0.0662 (19)	0.0509 (19)	0.0631 (18)	0.0062 (15)	0.0049 (15)	−0.0036 (14)
C14	0.0626 (19)	0.0565 (19)	0.0565 (17)	0.0017 (16)	0.0031 (14)	−0.0044 (14)
C15	0.081 (2)	0.052 (2)	0.082 (2)	0.0008 (18)	−0.0129 (19)	−0.0192 (17)
C16	0.081 (2)	0.0498 (19)	0.075 (2)	0.0078 (17)	−0.0021 (18)	−0.0101 (16)
C17	0.075 (2)	0.080 (3)	0.072 (2)	0.013 (2)	0.0000 (18)	−0.0022 (19)
C18	0.0569 (17)	0.0397 (15)	0.0550 (16)	−0.0012 (13)	0.0060 (13)	−0.0014 (13)
C19	0.0603 (19)	0.071 (2)	0.0634 (19)	0.0084 (17)	0.0082 (15)	−0.0124 (16)
C20	0.0579 (18)	0.070 (2)	0.0637 (19)	0.0051 (17)	0.0006 (15)	−0.0079 (17)
C21	0.0610 (18)	0.0501 (18)	0.0580 (17)	−0.0058 (14)	0.0075 (14)	−0.0049 (13)
C22	0.0625 (19)	0.077 (2)	0.0589 (18)	0.0100 (18)	0.0112 (15)	−0.0016 (17)
C23	0.0607 (18)	0.069 (2)	0.0574 (17)	0.0082 (16)	0.0049 (14)	0.0040 (15)

Br1—C21	1.890 (3)	C20—C21	1.377 (5)
O1—C14	1.367 (4)	C21—C22	1.377 (5)
O1—C17	1.419 (5)	C22—C23	1.381 (5)
N1—C1	1.355 (4)	C2—H2	0.9300
N1—C5	1.340 (4)	C6—H6A	0.9700
C1—C2	1.378 (4)	C6—H6B	0.9700
C1—C18	1.491 (4)	C7—H7A	0.9700
C2—C3	1.392 (4)	C7—H7B	0.9700
C3—C4	1.406 (4)	C8—H8A	0.9700
C3—C11	1.488 (4)	C8—H8B	0.9700
C4—C5	1.390 (4)	C9—H9A	0.9700
C4—C10	1.510 (5)	C9—H9B	0.9700
C5—C6	1.513 (5)	C10—H10A	0.9700
C6—C7	1.529 (6)	C10—H10B	0.9700
C7—C8	1.516 (5)	C12—H12	0.9300
C8—C9	1.509 (6)	C13—H13	0.9300
C9—C10	1.530 (6)	C15—H15	0.9300
C11—C12	1.380 (4)	C16—H16	0.9300
C11—C16	1.383 (5)	C17—H17A	0.9600
C12—C13	1.390 (5)	C17—H17B	0.9600
C13—C14	1.378 (4)	C17—H17C	0.9600
C14—C15	1.374 (5)	C19—H19	0.9300
C15—C16	1.375 (6)	C20—H20	0.9300
C18—C19	1.379 (5)	C22—H22	0.9300
C18—C23	1.390 (4)	C23—H23	0.9300
C19—C20	1.381 (5)
C14—O1—C17	117.6 (3)	C7—C6—H6B	109.00
C1—N1—C5	118.3 (2)	H6A—C6—H6B	108.00
N1—C1—C2	121.2 (3)	C6—C7—H7A	109.00
N1—C1—C18	115.2 (3)	C6—C7—H7B	109.00
C2—C1—C18	123.5 (3)	C8—C7—H7A	109.00
C1—C2—C3	120.9 (3)	C8—C7—H7B	109.00
C2—C3—C4	118.0 (3)	H7A—C7—H7B	108.00
C2—C3—C11	118.5 (3)	C7—C8—H8A	108.00
C4—C3—C11	123.6 (3)	C7—C8—H8B	108.00
C3—C4—C5	117.7 (3)	C9—C8—H8A	108.00
C3—C4—C10	122.2 (3)	C9—C8—H8B	108.00
C5—C4—C10	120.1 (3)	H8A—C8—H8B	107.00
N1—C5—C4	123.9 (3)	C8—C9—H9A	109.00
N1—C5—C6	114.3 (3)	C8—C9—H9B	109.00
C4—C5—C6	121.9 (3)	C10—C9—H9A	109.00
C5—C6—C7	114.2 (3)	C10—C9—H9B	109.00
C6—C7—C8	114.4 (3)	H9A—C9—H9B	108.00
C7—C8—C9	115.9 (3)	C4—C10—H10A	109.00
C8—C9—C10	114.4 (4)	C4—C10—H10B	109.00
C4—C10—C9	114.8 (3)	C9—C10—H10A	109.00
C3—C11—C12	120.8 (3)	C9—C10—H10B	109.00
C3—C11—C16	121.9 (3)	H10A—C10—H10B	108.00
C12—C11—C16	117.2 (3)	C11—C12—H12	119.00
C11—C12—C13	122.0 (3)	C13—C12—H12	119.00
C12—C13—C14	119.3 (3)	C12—C13—H13	120.00
O1—C14—C13	124.7 (3)	C14—C13—H13	120.00
O1—C14—C15	115.9 (3)	C14—C15—H15	120.00
C13—C14—C15	119.5 (3)	C16—C15—H15	120.00
C14—C15—C16	120.5 (4)	C11—C16—H16	119.00
C11—C16—C15	121.6 (4)	C15—C16—H16	119.00
C1—C18—C19	120.4 (3)	O1—C17—H17A	109.00
C1—C18—C23	122.2 (3)	O1—C17—H17B	109.00
C19—C18—C23	117.4 (3)	O1—C17—H17C	109.00
C18—C19—C20	121.9 (3)	H17A—C17—H17B	109.00
C19—C20—C21	119.3 (3)	H17A—C17—H17C	110.00
Br1—C21—C20	119.5 (2)	H17B—C17—H17C	110.00
Br1—C21—C22	120.0 (2)	C18—C19—H19	119.00
C20—C21—C22	120.5 (3)	C20—C19—H19	119.00
C21—C22—C23	119.2 (3)	C19—C20—H20	120.00
C18—C23—C22	121.7 (3)	C21—C20—H20	120.00
C1—C2—H2	120.00	C21—C22—H22	120.00
C3—C2—H2	120.00	C23—C22—H22	120.00
C5—C6—H6A	109.00	C18—C23—H23	119.00
C5—C6—H6B	109.00	C22—C23—H23	119.00
C7—C6—H6A	109.00
C17—O1—C14—C13	−3.6 (5)	C3—C4—C5—N1	−0.9 (5)
C17—O1—C14—C15	176.1 (3)	C4—C5—C6—C7	−62.8 (4)
C5—N1—C1—C2	−0.3 (5)	N1—C5—C6—C7	117.9 (3)
C1—N1—C5—C6	179.9 (3)	C5—C6—C7—C8	79.4 (4)
C1—N1—C5—C4	0.5 (5)	C6—C7—C8—C9	−62.9 (5)
C5—N1—C1—C18	179.0 (3)	C7—C8—C9—C10	61.7 (5)
C2—C1—C18—C19	171.9 (3)	C8—C9—C10—C4	−79.3 (4)
N1—C1—C18—C19	−7.4 (4)	C3—C11—C16—C15	176.5 (3)
N1—C1—C18—C23	172.3 (3)	C12—C11—C16—C15	0.0 (5)
N1—C1—C2—C3	0.5 (5)	C3—C11—C12—C13	−176.8 (3)
C2—C1—C18—C23	−8.4 (5)	C16—C11—C12—C13	−0.2 (5)
C18—C1—C2—C3	−178.7 (3)	C11—C12—C13—C14	0.3 (5)
C1—C2—C3—C4	−0.8 (4)	C12—C13—C14—C15	−0.2 (5)
C1—C2—C3—C11	179.8 (3)	C12—C13—C14—O1	179.4 (3)
C11—C3—C4—C10	2.3 (5)	O1—C14—C15—C16	−179.6 (3)
C11—C3—C4—C5	−179.7 (3)	C13—C14—C15—C16	0.0 (5)
C4—C3—C11—C12	−122.9 (3)	C14—C15—C16—C11	0.1 (6)
C2—C3—C11—C12	56.5 (4)	C1—C18—C19—C20	−178.5 (3)
C2—C3—C11—C16	−119.9 (4)	C23—C18—C19—C20	1.8 (5)
C2—C3—C4—C5	1.0 (4)	C1—C18—C23—C22	179.4 (3)
C4—C3—C11—C16	60.7 (4)	C19—C18—C23—C22	−0.9 (5)
C2—C3—C4—C10	−177.1 (3)	C18—C19—C20—C21	−0.9 (6)
C10—C4—C5—N1	177.3 (3)	C19—C20—C21—Br1	179.1 (3)
C5—C4—C10—C9	65.7 (4)	C19—C20—C21—C22	−1.0 (5)
C10—C4—C5—C6	−2.0 (5)	Br1—C21—C22—C23	−178.2 (3)
C3—C4—C10—C9	−116.2 (4)	C20—C21—C22—C23	1.8 (5)
C3—C4—C5—C6	179.8 (3)	C21—C22—C23—C18	−0.9 (5)