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

The title compound, C(24)H(18)BrNO, 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 inter-actions 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 = 416.30

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.105

S = 1.03

5341 reflections

244 parameters

H-atom parameters constrained

Δρmax = 1.64 e Å−3

Δρmin = −0.84 e Å−3

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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026553/tk2687Isup2.hkl

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

C24H18BrNO	F(000) = 848
Mr = 416.30	Dx = 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

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

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(Fo2) + (0.0531P)2 + 1.779P] where P = (Fo2 + 2Fc2)/3
5341 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 1.64 e Å−3
0 restraints	Δρmin = −0.83 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	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*

	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)

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)

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···Cg3iv	3.587 (8)	2.70	2.67

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⋯Cg3iv	3.587 (8)	2.70	2.67

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