2-(4-Bromo­phen­yl)-4-(4-meth­oxy­phen­yl)-6,7,8,9-tetra­hydro-5H-cyclo­hepta­[b]pyridine

Çelik, Í.; Akkurt, M.; Gezegen, H.; Kazak, C.

doi:10.1107/S1600536813013913

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o956

doi:10.1107/S1600536813013913

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2-(4-Bromophenyl)-4-(4-methoxyphenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine

Ísmail Çelik,^a ^* Mehmet Akkurt,^b Hayreddin Gezegen ^c and Canan Kazak ^d

^aDepartment of Physics, Faculty of Sciences, Cumhuriyet University, 58140 Sivas, Turkey, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^cDepartment of Physics, Faculty of Arts and Sciences, Gaziosmanpaşa University, 60240 Tokat, Turkey, and ^dDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: icelik@cumhuriyet.edu.tr

(Received 18 April 2013; accepted 20 May 2013; online 25 May 2013)

In the title compound, C₂₃H₂₂BrNO, the cycloheptane 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 interactions [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_r = 408.32
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.060
wR(F²) = 0.119
S = 1.12
3986 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813013913/rz5059sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813013913/rz5059Isup3.cml

checkCIF report

Comment top

Pyridine based heterocycles are found in structure of many natural and biologically important compounds (Aida et al., 2009; Laine-Cessac et al., 1997; Musiol et al., 2007). Also they are known to exhibit numerous biological and pharmacological properties such as antimicrobial (El-borai et al., 2012), antifungal (Khidre et al., 2011), antiviral (Cundy et al., 1997), anticancer (Rajanarendar et al., 2012), antioxidant (Hatanaka et al., 2005), anti-inflammatory (Girgis et al., 2007) and analgesic (Menegatti et al., 2006) activities. In this paper we report synthesis of 2-(4-bromophenyl)-4-(4-methoxyphenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine with high yield and its crystal structure.

The molecular structure of the title compound (I) is shown in Fig. 1. The cycloheptane ring (C4–C10) of (I) adopts a chair conformation [the puckering parameters (Cremer & Pople, 1975) are Q(2) = 0.422 (4) Å and ϕ(2) = 311.3 (5)°]. The pyridine ring (N1/C1–C5) makes dihedral angles of 58.63 (15) and 8.27 (16)° with the two benzene rings (C11–C16 and C18–C23), respectively, which have a dihedral angle of 56.68 (17)° between them.

The crystal packing is stabilized by C—Br···π interactions (C21—Br1···Cg1ⁱ: Br···A = 3.813 (2) Å, D—H···A = 126.25 (10)°; C21—Br1···Cg2ⁱⁱ: Br···A = 3.839 (2) Å, D—H···A = 138.31 (10)°; Cg1 and Cg2 are the centroids of the N1/C1–C5 and C11–C16 rings, respectively; symmetry codes: (i) x, 1/2-y, 1/2 + z; (ii) -x, -y, 1-z). Fig. 2 represents the molecular packing viewed down the b axis.

Related literature top

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 top

2-(4-Bromophenyl)-4-(4-methoxyphenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine was synthesized from the 1,5-diketone derivative (Ceylan & Gezegen, 2008) according to the literature method (Gezegen et al., 2010). To a solution of 2-[3-(4-bromophenyl)-1-(4-methoxyphenyl)-3-oxopropyl]cycloheptanone (1 mmol) in EtOH-AcOH (20 ml 1:1 v/v) was added NH₄Ac (4 mmol) and the mixture refluxed for 6 h. After completion of the reaction, the solvent was removed under vacuum and the residue was extracted with CH₂Cl₂ (2 × 25 ml). The organic layer was dried over Na₂SO₄ and evaporated. The crude product was purified by column chromatography (on a silica gel) eluting with hexane/CHCl₃ (3:1 v/v). The obtained brown product was crystallized from EtOH to give pure 2-(4-bromophenyl)-4-(4-methoxyphenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine in 95% yield; m. p. = 396–398 K.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); 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).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Packing diagram of the title compound viewed down the b axis.

2-(4-Bromophenyl)-4-(4-methoxyphenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine top

Crystal data top

C₂₃H₂₂BrNO	F(000) = 840
M_r = 408.32	D_x = 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

Data collection top

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	R_int = 0.178
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 2.0°
ω scans	h = −13→13
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
T_min = 0.355, T_max = 0.572	l = −23→23
28207 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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0476P)² + 0.6943P] where P = (F_o² + 2F_c²)/3
3986 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₂₃H₂₂BrNO	V = 1921.6 (14) Å³
M_r = 408.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.409 (5) Å	µ = 2.15 mm⁻¹
b = 10.054 (5) Å	T = 296 K
c = 18.428 (5) Å	0.58 × 0.42 × 0.26 mm
β = 94.850 (5)°

Data collection top

Stoe IPDS 2 diffractometer	3986 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	3083 reflections with I > 2σ(I)
T_min = 0.355, T_max = 0.572	R_int = 0.178
28207 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.12	Δρ_max = 0.67 e Å⁻³
3986 reflections	Δρ_min = −0.42 e Å⁻³
235 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₃H₂₂BrNO
M_r	408.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.409 (5), 10.054 (5), 18.428 (5)
β (°)	94.850 (5)
V (Å³)	1921.6 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.15
Crystal size (mm)	0.58 × 0.42 × 0.26

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.355, 0.572
No. of measured, independent and observed [I > 2σ(I)] reflections	28207, 3986, 3083
R_int	0.178
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.119, 1.12
No. of reflections	3986
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.42

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

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