8-Bromo-1,3-diphenyl-2,3-dihydro-1H-naphtho­[1,2-e][1,3]oxazine

Jasinski, J.P.; Pek, A.E.; Mayekar, A.N.; Yathirajan, H.S.; Narayana, B.

doi:10.1107/S1600536810026553

organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Pages o2053-o2054

https://doi.org/10.1107/S1600536810026553

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8-Bromo-1,3-diphenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine

Jerry P. Jasinski,^a ^* Albert E. Pek,^a A. N. Mayekar,^b H. S. Yathirajan ^c and B. Narayana ^d

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and SeQuent Scientific Ltd, Baikampady, New Mangalore 575 011 India, ^cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^dDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 1 July 2010; accepted 5 July 2010; online 17 July 2010)

The title compound, C₂₄H₁₈BrNO, consists of an envelope-configured oxazine ring with a fused 8-bromo-1,3-diphenyl group and two bonded phenyl rings. The dihedral angles between the mean planes of the 8-bromo-1,3-diphenyl and the phenyl rings are 54.5 (6) and 87.4 (8)°, respectively. The oxazine is essentially coplanar with the 8-bromo-1,3-diphenyl [dihedral angle = 9.4 (1)°]. Weak C—H⋯π interactions contribute to the crystal packing.

Related literature

For the antitumor activity of heterocycles containing oxazine, see: Benameur et al. (1996 ). For the treatment of Parkinson's disease with naphthoxazines, see: Millan et al. (2004 ); Joyce et al. (2003 ). For the psychostimulating and antidepressant activity of oxazines, see: Nozulak & Giger (1987 ). For their analgesic, anticonvulsant, antitubercular, antibacterial and anticancer activity, see: Kurz (2005 ); Turgut et al. (2007 ). For the range of their biological applications, see: Ohnacker & Scheffler (1960 ). For synthetic possibilities, see: Szatmari et al. (2003 , 2004 ). For anticancer derivatives, see: Zhang & Li (2003 ). For related structures, see: Li et al. (2008 ); Sarojini et al. (2007 ); Şen et al. (2008 ); Yang et al. (2008 ); Zhang et al. (2009 ).

Experimental

Crystal data

C₂₄H₁₈BrNO
M_r = 416.30
Monoclinic, P 2₁ /c
a = 7.7617 (11) Å
b = 20.092 (3) Å
c = 11.5094 (16) Å
β = 91.893 (2)°
V = 1793.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.31 mm⁻¹
T = 100 K
0.55 × 0.50 × 0.35 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.364, T_max = 0.499
14693 measured reflections
5341 independent reflections
4426 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.105
S = 1.03
5341 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 1.64 e Å⁻³
Δρ_min = −0.84 e Å⁻³

Table 1
C—H⋯π interactions (Å)

Cg3, Cg4 and Cg5 are the centroids of the C4/C5/C7–C16, C13–C18 and C19–C24 rings, respectively.

X—H⋯Cg	X⋯Cg	H⋯Cg	H⋯Perp
C1–H1⋯Cg5ⁱ	3.357 (8)	2.80	2.67
C24–H18⋯Cg3ⁱⁱ	3.692 (9)	2.93	2.90
C22–H21⋯Cg4ⁱⁱⁱ	3.547 (3)	2.68	2.61
C17–H24⋯Cg3^iv	3.587 (8)	2.70	2.67
Symmetry codes: (i) −x, $[{1\over 2}]$ + y, $[{1\over 2}]$ − z; (ii) −x, −y, 1 − z; (iii) −x, − $[{1\over 2}]$ + y, $[{1\over 2}]$ − z; (iv) −1 + x, y, z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810026553/tk2687sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810026553/tk2687Isup2.hkl

checkCIF report

Comment top

Heterocycles containing the oxazine nucleus are found to possess a wide range of biological applications (Ohnacker & Scheffler et al., 1960). 1,3-Oxazine heterocycles are of interest because they constitute an important class of natural and non-natural products. Many of them exhibit biological activity such as analgesic, anticonvulsant, antitubercular, antibacterial and anticancer (Kurz et al., 2005; Turgut et al., 2007). 1,3-Oxazine derivatives that display anticancer activity are also known as progesterone receptor agonists (Zhang et al., 2003). Oxazine derivatives with a naphthalene ring, termed naphthoxazines, are used in the treatment of Parkinson's disease (Millan et al., 2004; Joyce et al., 2003). Naphthoxazines are also known for their psychostimulating and antidepressant activity (Nozulak & Giger et al., 1987). Dihydrofuronaphth[1,3]oxazines have shown anti-tumor activity (Benameur et al., 1996). In addition, naphthoxazines can be used as intermediates in the synthesis of N-substituted amino alcohols or in enantioselective synthesis of chiral amines. The tautomeric character of the 1,3-O,N-heterocycles offers a great number of synthetic possibilities (Szatmari et al., 2003; Szatmari et al., 2004). The crystal structures of a few naphthoxazines viz., 6-bromo-2,4-bis(3-methoxyphenyl)-3,4-dihydro-2H-1,3-naphthoxazine (Sarojini et al., 2007), 3-(1,3 -benzodioxol-5-yl)-1-phenyl-2, 3-dihydro-1H-naphtho[1,2-e][1,3]oxazine (Yang et al., 2008), 2-butyl-1,3-diphenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine (Li et al., 2008), 1,3-di-3-pyridyl-2, 3-dihydro-1H-naphth-[1,2-e][1,3]oxazine (Şen et al., 2008) and 2-benzyl-1,3-diphenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine (Zhang et al., 2009) have been reported. In view of the importance of naphthoxazines, this paper reports the synthesis and crystal structure of the title compound, (I).

Compound (I) consists of an envelope configured oxazine (C8/C7/C11/N2/C12/O1) ring with a fused 8-bromo-1,3-diphenyl group and two bonded benzene rings (at C11 and C12) [puckering parameters Q, θ and φ = 0.460 (6) Å, 54.2 (7) °, and 259.144 (8) °, respectively] (Fig 1.); for an ideal envelope θ has a value of 54.7°. The dihedral angles between the mean planes of the 8-bromo-1,3-diphenyl (C1—C10) and the benzene rings (C13—C18 and C19—C24) are 54.5 (6) and 87.4 (8) °, respectively. The oxazine ring (C7/C8/O1/C12/N1) is essentially co-planar (dihedral angle = 9.4 (1)°) to the 8-bromo-1,3-diphenyl ring. Weak C–H···π interactions (Table 1) (Spek, 2003) are observed which contribute to crystal stability (Fig. 2).

Related literature top

For the antitumor activity of heterocycles containing oxazine, see: Benameur et al. (1996). For the treatment of Parkinson's disease with naphthoxazines, see: Millan et al. (2004); Joyce et al. (2003). For their psychostimulating and antidepressant activity, see: Nozulak & Giger et al. (1987). For their analgesic, anticonvulsant, antitubercular, antibacterial and anticancer activity, see: Kurz et al. (2005); Turgut et al. (2007). For the range of their biological applications, see: Ohnacker & Scheffler et al. (1960). For synthetic possibilities, see: Szatmari et al. (2003, 2004). For anticancer derivatives, see: Zhang et al. (2003). For related structures, see: Li et al. (2008); Sarojini et al. (2007); Şen et al. (2008); Yang et al. (2008); Zhang et al. (2009).

Experimental top

Benzaldehyde (2.12 g, 0.02 mol) and 25–30% methanolic ammonia (10 ml) were added to 6-bromo-2-naphthol (2.23 g, 0.01 mol) in methanol (10 ml). The mixture was left to stand at ambient temperature for 3 days, during which the crystalline product separated out. The crude product was filtered off and washed with cold methanol. Crystals suitable for X-ray diffraction studies were grown by the slow evaporation of the acetonitrile solution (m.pt. 423–425 K).

Structure description top

For the antitumor activity of heterocycles containing oxazine, see: Benameur et al. (1996). For the treatment of Parkinson's disease with naphthoxazines, see: Millan et al. (2004); Joyce et al. (2003). For their psychostimulating and antidepressant activity, see: Nozulak & Giger et al. (1987). For their analgesic, anticonvulsant, antitubercular, antibacterial and anticancer activity, see: Kurz et al. (2005); Turgut et al. (2007). For the range of their biological applications, see: Ohnacker & Scheffler et al. (1960). For synthetic possibilities, see: Szatmari et al. (2003, 2004). For anticancer derivatives, see: Zhang et al. (2003). For related structures, see: Li et al. (2008); Sarojini et al. (2007); Şen et al. (2008); Yang et al. (2008); Zhang et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of (I) showing the atom labeling scheme and 40% probability displacement ellipsoids.
	Fig. 2. Packing diagram of (I) viewed down the c axis.

8-Bromo-1,3-diphenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine top

Crystal data top

C₂₄H₁₈BrNO	F(000) = 848
M_r = 416.30	D_x = 1.541 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5049 reflections
a = 7.7617 (11) Å	θ = 2.6–31.2°
b = 20.092 (3) Å	µ = 2.31 mm⁻¹
c = 11.5094 (16) Å	T = 100 K
β = 91.893 (2)°	Block, colourless
V = 1793.9 (4) Å³	0.55 × 0.50 × 0.35 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	5341 independent reflections
Radiation source: fine-focus sealed tube	4426 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 31.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→10
T_min = 0.364, T_max = 0.499	k = −22→28
14693 measured reflections	l = −16→16

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0531P)² + 1.779P] where P = (F_o² + 2F_c²)/3
5341 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 1.64 e Å⁻³
0 restraints	Δρ_min = −0.84 e Å⁻³

Crystal data top

C₂₄H₁₈BrNO	V = 1793.9 (4) Å³
M_r = 416.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7617 (11) Å	µ = 2.31 mm⁻¹
b = 20.092 (3) Å	T = 100 K
c = 11.5094 (16) Å	0.55 × 0.50 × 0.35 mm
β = 91.893 (2)°

Data collection top

Bruker APEXII CCD diffractometer	5341 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4426 reflections with I > 2σ(I)
T_min = 0.364, T_max = 0.499	R_int = 0.025
14693 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.03	Δρ_max = 1.64 e Å⁻³
5341 reflections	Δρ_min = −0.84 e Å⁻³
244 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	0.26837 (3)	0.385264 (10)	0.377762 (19)	0.02407 (8)
C11	0.1161 (2)	0.04955 (10)	0.22310 (16)	0.0149 (4)
H16	0.1739	0.0708	0.1584	0.018*
C7	0.1858 (2)	0.08276 (10)	0.33364 (16)	0.0137 (3)
C5	0.2088 (2)	0.15294 (10)	0.34152 (16)	0.0144 (3)
C8	0.2413 (3)	0.04374 (10)	0.42586 (16)	0.0149 (4)
C4	0.2910 (2)	0.18121 (10)	0.44282 (16)	0.0153 (4)
C9	0.3260 (3)	0.07139 (10)	0.52570 (17)	0.0172 (4)
H9	0.3645	0.0437	0.5860	0.021*
C10	0.3511 (3)	0.13830 (11)	0.53356 (17)	0.0177 (4)
H10	0.4081	0.1561	0.5988	0.021*
C3	0.3107 (3)	0.25095 (10)	0.45246 (17)	0.0169 (4)
H3	0.3651	0.2693	0.5181	0.020*
C2	0.2494 (3)	0.29135 (11)	0.36489 (18)	0.0185 (4)
C1	0.1708 (3)	0.26470 (11)	0.26294 (18)	0.0193 (4)
H1	0.1321	0.2928	0.2034	0.023*
C6	0.1517 (3)	0.19715 (10)	0.25210 (17)	0.0170 (4)
H6	0.1000	0.1799	0.1846	0.020*
N1	0.1653 (3)	−0.02094 (9)	0.22166 (16)	0.0231 (4)
H2	0.2104	−0.0405	0.1636	0.028*
C12	0.1297 (3)	−0.05220 (11)	0.32674 (19)	0.0220 (4)
H13	0.0061	−0.0483	0.3402	0.026*
O1	0.2269 (2)	−0.02379 (7)	0.42750 (12)	0.0207 (3)
C13	−0.0762 (2)	0.05797 (9)	0.19911 (16)	0.0131 (3)
C14	−0.1404 (3)	0.05611 (10)	0.08416 (17)	0.0154 (4)
H27	−0.0651	0.0515	0.0235	0.018*
C19	0.1801 (3)	−0.12560 (11)	0.33218 (19)	0.0232 (4)
C24	0.1387 (3)	−0.16039 (11)	0.43087 (18)	0.0215 (4)
H18	0.0831	−0.1385	0.4901	0.026*
C22	0.2638 (3)	−0.26054 (12)	0.3568 (2)	0.0261 (5)
H21	0.2919	−0.3053	0.3654	0.031*
C23	0.1781 (3)	−0.22716 (11)	0.44351 (19)	0.0233 (4)
H22	0.1473	−0.2498	0.5102	0.028*
C20	0.2633 (3)	−0.15863 (12)	0.2441 (2)	0.0279 (5)
H19	0.2902	−0.1361	0.1765	0.033*
C21	0.3069 (3)	−0.22641 (13)	0.2574 (2)	0.0284 (5)
H20	0.3648	−0.2483	0.1991	0.034*
C15	−0.3168 (3)	0.06123 (11)	0.06044 (18)	0.0196 (4)
H26	−0.3592	0.0590	−0.0160	0.023*
C18	−0.1906 (3)	0.06585 (10)	0.28794 (17)	0.0167 (4)
H23	−0.1490	0.0669	0.3646	0.020*
C17	−0.3669 (3)	0.07221 (11)	0.26411 (19)	0.0213 (4)
H24	−0.4421	0.0781	0.3245	0.026*
C16	−0.4300 (3)	0.06968 (11)	0.1503 (2)	0.0222 (4)
H25	−0.5477	0.0736	0.1340	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03207 (13)	0.01420 (11)	0.02574 (12)	0.00133 (8)	−0.00214 (8)	0.00038 (8)
C11	0.0146 (8)	0.0182 (9)	0.0117 (8)	0.0015 (7)	0.0003 (6)	−0.0008 (7)
C7	0.0106 (8)	0.0179 (9)	0.0127 (8)	−0.0001 (7)	0.0007 (6)	0.0006 (7)
C5	0.0114 (8)	0.0183 (9)	0.0136 (8)	0.0001 (7)	−0.0003 (6)	0.0010 (7)
C8	0.0179 (9)	0.0130 (9)	0.0138 (8)	−0.0031 (7)	0.0021 (7)	0.0006 (7)
C4	0.0147 (8)	0.0167 (9)	0.0144 (8)	0.0003 (7)	0.0011 (6)	−0.0002 (7)
C9	0.0229 (10)	0.0164 (9)	0.0122 (8)	−0.0002 (7)	−0.0018 (7)	0.0020 (7)
C10	0.0228 (10)	0.0171 (9)	0.0130 (8)	−0.0006 (7)	−0.0030 (7)	−0.0005 (7)
C3	0.0181 (9)	0.0148 (9)	0.0177 (9)	0.0003 (7)	−0.0002 (7)	−0.0014 (7)
C2	0.0196 (9)	0.0150 (9)	0.0209 (9)	0.0007 (7)	0.0017 (7)	0.0014 (7)
C1	0.0184 (9)	0.0198 (10)	0.0194 (9)	0.0017 (7)	−0.0024 (7)	0.0034 (8)
C6	0.0161 (9)	0.0190 (9)	0.0158 (8)	0.0005 (7)	−0.0018 (7)	0.0016 (7)
N1	0.0328 (10)	0.0190 (9)	0.0171 (8)	0.0099 (7)	−0.0040 (7)	−0.0050 (7)
C12	0.0231 (10)	0.0217 (10)	0.0210 (10)	−0.0012 (8)	−0.0007 (8)	−0.0004 (8)
O1	0.0352 (8)	0.0141 (7)	0.0127 (6)	−0.0047 (6)	−0.0025 (6)	0.0015 (5)
C13	0.0133 (8)	0.0110 (8)	0.0151 (8)	−0.0006 (6)	0.0003 (6)	0.0008 (6)
C14	0.0172 (9)	0.0139 (9)	0.0150 (8)	0.0003 (7)	−0.0006 (7)	−0.0001 (7)
C19	0.0342 (12)	0.0167 (10)	0.0184 (9)	−0.0058 (8)	−0.0035 (8)	−0.0003 (7)
C24	0.0310 (11)	0.0160 (10)	0.0172 (9)	−0.0010 (8)	−0.0044 (8)	−0.0007 (7)
C22	0.0271 (11)	0.0185 (10)	0.0322 (12)	0.0030 (8)	−0.0083 (9)	−0.0003 (9)
C23	0.0323 (11)	0.0170 (10)	0.0202 (9)	−0.0038 (8)	−0.0049 (8)	0.0040 (8)
C20	0.0375 (13)	0.0260 (12)	0.0202 (10)	−0.0105 (10)	0.0029 (9)	−0.0002 (9)
C21	0.0252 (11)	0.0316 (13)	0.0285 (11)	−0.0040 (9)	0.0024 (9)	−0.0091 (10)
C15	0.0167 (9)	0.0214 (10)	0.0202 (9)	−0.0025 (7)	−0.0060 (7)	0.0015 (8)
C18	0.0183 (9)	0.0178 (9)	0.0140 (8)	−0.0001 (7)	0.0015 (7)	0.0026 (7)
C17	0.0156 (9)	0.0228 (10)	0.0259 (10)	0.0000 (8)	0.0055 (8)	0.0060 (8)
C16	0.0125 (9)	0.0226 (10)	0.0313 (11)	−0.0033 (7)	−0.0018 (8)	0.0084 (9)

Geometric parameters (Å, º) top

Br1—C2	1.898 (2)	C12—C19	1.527 (3)
C11—N1	1.467 (3)	C12—H13	0.9800
C11—C13	1.518 (3)	C13—C18	1.385 (3)
C11—C7	1.520 (3)	C13—C14	1.399 (3)
C11—H16	0.9800	C14—C15	1.391 (3)
C7—C8	1.377 (3)	C14—H27	0.9300
C7—C5	1.424 (3)	C19—C24	1.381 (3)
C5—C6	1.420 (3)	C19—C20	1.388 (3)
C5—C4	1.428 (3)	C24—C23	1.383 (3)
C8—O1	1.361 (2)	C24—H18	0.9300
C8—C9	1.418 (3)	C22—C21	1.384 (4)
C4—C3	1.414 (3)	C22—C23	1.390 (3)
C4—C10	1.421 (3)	C22—H21	0.9300
C9—C10	1.361 (3)	C23—H22	0.9300
C9—H9	0.9300	C20—C21	1.410 (4)
C10—H10	0.9300	C20—H19	0.9300
C3—C2	1.367 (3)	C21—H20	0.9300
C3—H3	0.9300	C15—C16	1.389 (3)
C2—C1	1.410 (3)	C15—H26	0.9300
C1—C6	1.370 (3)	C18—C17	1.393 (3)
C1—H1	0.9300	C18—H23	0.9300
C6—H6	0.9300	C17—C16	1.384 (3)
N1—C12	1.399 (3)	C17—H24	0.9300
N1—H2	0.8600	C16—H25	0.9300
C12—O1	1.477 (3)

N1—C11—C13	111.12 (16)	O1—C12—C19	102.55 (16)
N1—C11—C7	110.33 (15)	N1—C12—H13	108.8
C13—C11—C7	115.09 (16)	O1—C12—H13	108.8
N1—C11—H16	106.6	C19—C12—H13	108.8
C13—C11—H16	106.6	C8—O1—C12	114.47 (15)
C7—C11—H16	106.6	C18—C13—C14	118.95 (17)
C8—C7—C5	118.64 (17)	C18—C13—C11	121.92 (17)
C8—C7—C11	119.26 (18)	C14—C13—C11	119.11 (17)
C5—C7—C11	121.90 (16)	C15—C14—C13	120.09 (19)
C6—C5—C7	122.55 (17)	C15—C14—H27	120.0
C6—C5—C4	117.61 (18)	C13—C14—H27	120.0
C7—C5—C4	119.84 (17)	C24—C19—C20	119.0 (2)
O1—C8—C7	123.66 (17)	C24—C19—C12	117.2 (2)
O1—C8—C9	114.54 (17)	C20—C19—C12	123.8 (2)
C7—C8—C9	121.75 (18)	C19—C24—C23	121.4 (2)
C3—C4—C10	120.77 (18)	C19—C24—H18	119.3
C3—C4—C5	120.17 (18)	C23—C24—H18	119.3
C10—C4—C5	119.06 (18)	C21—C22—C23	119.2 (2)
C10—C9—C8	120.16 (18)	C21—C22—H21	120.4
C10—C9—H9	119.9	C23—C22—H21	120.4
C8—C9—H9	119.9	C24—C23—C22	120.1 (2)
C9—C10—C4	120.50 (18)	C24—C23—H22	119.9
C9—C10—H10	119.8	C22—C23—H22	119.9
C4—C10—H10	119.8	C19—C20—C21	119.9 (2)
C2—C3—C4	119.77 (18)	C19—C20—H19	120.1
C2—C3—H3	120.1	C21—C20—H19	120.1
C4—C3—H3	120.1	C22—C21—C20	120.3 (2)
C3—C2—C1	121.2 (2)	C22—C21—H20	119.8
C3—C2—Br1	120.56 (16)	C20—C21—H20	119.8
C1—C2—Br1	118.21 (15)	C16—C15—C14	120.37 (19)
C6—C1—C2	119.62 (19)	C16—C15—H26	119.8
C6—C1—H1	120.2	C14—C15—H26	119.8
C2—C1—H1	120.2	C13—C18—C17	120.99 (18)
C1—C6—C5	121.57 (18)	C13—C18—H23	119.5
C1—C6—H6	119.2	C17—C18—H23	119.5
C5—C6—H6	119.2	C16—C17—C18	119.8 (2)
C12—N1—C11	111.40 (17)	C16—C17—H24	120.1
C12—N1—H2	124.3	C18—C17—H24	120.1
C11—N1—H2	124.3	C17—C16—C15	119.76 (19)
N1—C12—O1	113.24 (18)	C17—C16—H25	120.1
N1—C12—C19	114.31 (19)	C15—C16—H25	120.1

N1—C11—C7—C8	−16.2 (2)	C7—C11—N1—C12	48.5 (2)
C13—C11—C7—C8	110.5 (2)	C11—N1—C12—O1	−62.2 (2)
N1—C11—C7—C5	158.55 (18)	C11—N1—C12—C19	−179.14 (17)
C13—C11—C7—C5	−74.7 (2)	C7—C8—O1—C12	−6.1 (3)
C8—C7—C5—C6	−178.32 (19)	C9—C8—O1—C12	176.55 (18)
C11—C7—C5—C6	6.9 (3)	N1—C12—O1—C8	39.9 (2)
C8—C7—C5—C4	1.2 (3)	C19—C12—O1—C8	163.56 (18)
C11—C7—C5—C4	−173.63 (17)	N1—C11—C13—C18	97.4 (2)
C5—C7—C8—O1	−179.57 (18)	C7—C11—C13—C18	−28.9 (3)
C11—C7—C8—O1	−4.6 (3)	N1—C11—C13—C14	−81.0 (2)
C5—C7—C8—C9	−2.4 (3)	C7—C11—C13—C14	152.64 (18)
C11—C7—C8—C9	172.48 (18)	C18—C13—C14—C15	−0.9 (3)
C6—C5—C4—C3	1.0 (3)	C11—C13—C14—C15	177.60 (19)
C7—C5—C4—C3	−178.53 (18)	N1—C12—C19—C24	−176.1 (2)
C6—C5—C4—C10	−179.44 (18)	O1—C12—C19—C24	60.9 (2)
C7—C5—C4—C10	1.1 (3)	N1—C12—C19—C20	3.5 (3)
O1—C8—C9—C10	178.84 (19)	O1—C12—C19—C20	−119.5 (2)
C7—C8—C9—C10	1.5 (3)	C20—C19—C24—C23	0.0 (3)
C8—C9—C10—C4	0.8 (3)	C12—C19—C24—C23	179.6 (2)
C3—C4—C10—C9	177.5 (2)	C19—C24—C23—C22	1.1 (3)
C5—C4—C10—C9	−2.1 (3)	C21—C22—C23—C24	−0.8 (3)
C10—C4—C3—C2	−179.0 (2)	C24—C19—C20—C21	−1.2 (3)
C5—C4—C3—C2	0.6 (3)	C12—C19—C20—C21	179.2 (2)
C4—C3—C2—C1	−1.9 (3)	C23—C22—C21—C20	−0.4 (3)
C4—C3—C2—Br1	178.18 (15)	C19—C20—C21—C22	1.4 (4)
C3—C2—C1—C6	1.5 (3)	C13—C14—C15—C16	1.4 (3)
Br1—C2—C1—C6	−178.55 (16)	C14—C13—C18—C17	−0.3 (3)
C2—C1—C6—C5	0.2 (3)	C11—C13—C18—C17	−178.75 (19)
C7—C5—C6—C1	178.12 (19)	C13—C18—C17—C16	1.0 (3)
C4—C5—C6—C1	−1.4 (3)	C18—C17—C16—C15	−0.4 (3)
C13—C11—N1—C12	−80.4 (2)	C14—C15—C16—C17	−0.8 (3)

Experimental details

Crystal data
Chemical formula	C₂₄H₁₈BrNO
M_r	416.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.7617 (11), 20.092 (3), 11.5094 (16)
β (°)	91.893 (2)
V (Å³)	1793.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.31
Crystal size (mm)	0.55 × 0.50 × 0.35

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.364, 0.499
No. of measured, independent and observed [I > 2σ(I)] reflections	14693, 5341, 4426
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.731

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.105, 1.03
No. of reflections	5341
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.64, −0.84

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

C—H···π interactions (Å) top

Cg3, Cg4 and Cg5 are the centroids of the C4/C5/C7–C16, C13–C18 and C19–C24 rings, respectively.

X—H···Cg	X···Cg	H···Cg	H···Perp
C1–H1···Cg5ⁱ	3.357 (8)	2.80	2.67
C24–H18···Cg3ⁱⁱ	3.692 (9)	2.93	2.90
C22–H21···Cg4ⁱⁱⁱ	3.547 (3)	2.68	2.61
C17–H24···Cg3^iv	3.587 (8)	2.70	2.67

Symmetry codes: (i) -x, 1/2+y, 1/2-z ; (ii) -x, -y, 1-z ; (iii) -x, -1/2+y, 1/2-z ; (iv) -1+x, y, z.

Acknowledgements

JPJ thanks Dr Matthias Zeller and the YSU Department of Chemistry for their assistance with the data collection. The diffractometer was funded by NSF grant 0087210, by Ohio Board of Regents grant CAP-491, and by YSU. ANM thanks the University of Mysore and SeQuent Scientific Ltd for research facilities and HSY thanks the University of Mysore for sabbatical leave.

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