(4-Bromo-phen-yl)(2,7-dimeth-oxy-1-naphth-yl)methanone.

In the title compound, C(19)H(15)BrO(3), the dihedral angle between the naphthalene ring system and the benzene ring is 72.02 (9)°. The bridging carbonyl C-C(=O)-C plane makes dihedral angles of 70.88 (10) and 1.87 (12)°, respectively, with the naphthalene ring system and the benzene ring. In the crystal, two types of weak inter-molecular C-H⋯O inter-actions and a short Br⋯C contact [3.345 (2) Å] are observed.

Related literature

For electrophilic aromatic substitution of naphthalene deriva­tives, see: Okamoto & Yonezawa (2009 ▶). For the structures of closely related compounds, see: Hijikata et al., 2010 ▶); Kato, Nagasawa, Hijikata et al. (2010 ▶); Kato, Nagasawa, Kataoka et al. (2010 ▶); Muto et al. (2010 ▶); Watanabe, Muto et al. (2010 ▶); Watanabe, Nakaema et al. (2010 ▶).

Experimental

Crystal data

C19H15BrO3

M = 371.22

Orthorhombic,

a = 6.58278 (12) Å

b = 16.1134 (3) Å

c = 30.2750 (6) Å

V = 3211.30 (10) Å3

Z = 8

Cu Kα radiation

μ = 3.60 mm−1

T = 193 K

0.60 × 0.60 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.161, T max = 0.533

52243 measured reflections

2922 independent reflections

2724 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.082

S = 1.06

2922 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.67 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810042662/is2618sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042662/is2618Isup2.hkl

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

C19H15BrO3	Dx = 1.536 Mg m−3
Mr = 371.22	Melting point = 405.2–408.7 K
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 50764 reflections
a = 6.58278 (12) Å	θ = 3.1–68.2°
b = 16.1134 (3) Å	µ = 3.60 mm−1
c = 30.2750 (6) Å	T = 193 K
V = 3211.30 (10) Å3	Platelet, colorless
Z = 8	0.60 × 0.60 × 0.20 mm
F(000) = 1504

Rigaku R-AXIS RAPID diffractometer	2922 independent reflections
Radiation source: rotating anode	2724 reflections with I > 2σ(I)
graphite	Rint = 0.033
Detector resolution: 10.00 pixels mm-1	θmax = 68.3°, θmin = 5.5°
ω scans	h = −7→7
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −19→19
Tmin = 0.161, Tmax = 0.533	l = −36→36
52243 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033	H-atom parameters constrained
wR(F2) = 0.082	w = 1/[σ2(Fo2) + (0.0352P)2 + 2.8492P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2922 reflections	Δρmax = 0.73 e Å−3
211 parameters	Δρmin = −0.67 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00189 (8)

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	0.81329 (5)	0.125182 (16)	0.029041 (9)	0.05922 (14)
O1	0.5963 (3)	0.05334 (10)	−0.18778 (5)	0.0474 (4)
O2	−0.2447 (3)	−0.17865 (10)	−0.10564 (6)	0.0520 (4)
O3	0.1223 (2)	0.08709 (10)	−0.13828 (6)	0.0487 (4)
C1	0.4972 (3)	−0.02136 (13)	−0.18754 (7)	0.0374 (5)
C2	0.5580 (4)	−0.08984 (15)	−0.21337 (7)	0.0435 (5)
H2	0.6741	−0.0861	−0.2319	0.052*
C3	0.4479 (4)	−0.16140 (14)	−0.21143 (7)	0.0431 (5)
H3	0.4914	−0.2078	−0.2283	0.052*
C4	0.2719 (4)	−0.16887 (13)	−0.18527 (6)	0.0366 (5)
C5	0.1554 (4)	−0.24241 (13)	−0.18287 (7)	0.0428 (5)
H5	0.1968	−0.2893	−0.1996	0.051*
C6	−0.0143 (4)	−0.24819 (13)	−0.15728 (7)	0.0438 (5)
H6	−0.0894	−0.2985	−0.1562	0.053*
C7	−0.0776 (3)	−0.17878 (13)	−0.13235 (7)	0.0388 (5)
C8	0.0304 (3)	−0.10607 (12)	−0.13367 (7)	0.0348 (4)
H8	−0.0151	−0.0598	−0.1170	0.042*
C9	0.2085 (3)	−0.09892 (12)	−0.15950 (6)	0.0322 (4)
C10	0.3289 (3)	−0.02594 (12)	−0.16062 (6)	0.0331 (4)
C11	0.2740 (3)	0.04610 (12)	−0.13110 (7)	0.0336 (4)
C12	0.4065 (3)	0.06341 (12)	−0.09228 (6)	0.0322 (4)
C13	0.3595 (4)	0.12986 (14)	−0.06479 (8)	0.0458 (6)
H13	0.2440	0.1632	−0.0710	0.055*
C14	0.4791 (4)	0.14768 (15)	−0.02861 (8)	0.0514 (6)
H14	0.4468	0.1931	−0.0099	0.062*
C15	0.6459 (4)	0.09888 (14)	−0.01995 (7)	0.0410 (5)
C16	0.6948 (4)	0.03213 (14)	−0.04623 (8)	0.0430 (5)
H16	0.8101	−0.0012	−0.0397	0.052*
C17	0.5735 (3)	0.01439 (13)	−0.08224 (7)	0.0385 (5)
H17	0.6048	−0.0320	−0.1004	0.046*
C18	0.7728 (4)	0.06171 (18)	−0.21481 (8)	0.0534 (6)
H18A	0.8301	0.1174	−0.2111	0.064*
H18B	0.7357	0.0533	−0.2458	0.064*
H18C	0.8738	0.0201	−0.2061	0.064*
C19	−0.3709 (4)	−0.25055 (15)	−0.10462 (10)	0.0570 (7)
H19A	−0.4878	−0.2403	−0.0853	0.068*
H19B	−0.2930	−0.2978	−0.0933	0.068*
H19C	−0.4188	−0.2630	−0.1345	0.068*

	U11	U22	U33	U12	U13	U23
Br1	0.0793 (2)	0.04578 (18)	0.05256 (19)	−0.00079 (13)	−0.02664 (14)	−0.00441 (11)
O1	0.0446 (9)	0.0476 (9)	0.0499 (9)	−0.0074 (8)	0.0127 (7)	−0.0077 (7)
O2	0.0498 (9)	0.0384 (8)	0.0678 (11)	−0.0113 (8)	0.0073 (9)	−0.0016 (8)
O3	0.0400 (9)	0.0376 (8)	0.0684 (11)	0.0100 (7)	−0.0141 (8)	−0.0134 (8)
C1	0.0381 (11)	0.0380 (11)	0.0361 (10)	0.0026 (9)	−0.0025 (9)	−0.0024 (8)
C2	0.0434 (13)	0.0516 (13)	0.0356 (11)	0.0099 (11)	0.0031 (9)	−0.0046 (10)
C3	0.0537 (14)	0.0394 (12)	0.0362 (11)	0.0153 (10)	−0.0024 (10)	−0.0089 (9)
C4	0.0465 (12)	0.0311 (10)	0.0323 (10)	0.0095 (9)	−0.0099 (9)	−0.0034 (8)
C5	0.0586 (15)	0.0302 (11)	0.0397 (11)	0.0087 (10)	−0.0109 (10)	−0.0055 (9)
C6	0.0570 (14)	0.0272 (10)	0.0474 (12)	−0.0015 (10)	−0.0151 (11)	0.0008 (9)
C7	0.0410 (12)	0.0347 (11)	0.0408 (11)	−0.0001 (9)	−0.0073 (9)	0.0025 (9)
C8	0.0383 (11)	0.0290 (10)	0.0370 (10)	0.0030 (9)	−0.0049 (9)	−0.0024 (8)
C9	0.0363 (11)	0.0288 (10)	0.0315 (10)	0.0064 (8)	−0.0082 (8)	−0.0010 (8)
C10	0.0341 (11)	0.0313 (10)	0.0337 (10)	0.0052 (8)	−0.0035 (8)	−0.0036 (8)
C11	0.0325 (11)	0.0273 (10)	0.0409 (11)	0.0001 (8)	0.0012 (9)	−0.0010 (8)
C12	0.0343 (10)	0.0264 (9)	0.0359 (10)	0.0003 (8)	0.0025 (8)	0.0003 (8)
C13	0.0521 (14)	0.0371 (12)	0.0482 (13)	0.0159 (10)	−0.0060 (11)	−0.0082 (9)
C14	0.0690 (17)	0.0387 (12)	0.0464 (13)	0.0149 (12)	−0.0109 (12)	−0.0121 (10)
C15	0.0539 (14)	0.0320 (10)	0.0372 (11)	−0.0042 (10)	−0.0090 (10)	0.0008 (9)
C16	0.0441 (13)	0.0392 (12)	0.0457 (12)	0.0076 (10)	−0.0060 (10)	−0.0015 (10)
C17	0.0401 (12)	0.0339 (11)	0.0416 (11)	0.0063 (9)	−0.0001 (9)	−0.0048 (9)
C18	0.0423 (13)	0.0665 (16)	0.0515 (13)	−0.0103 (12)	0.0106 (11)	−0.0061 (12)
C19	0.0532 (15)	0.0431 (13)	0.0747 (17)	−0.0137 (12)	−0.0049 (13)	0.0122 (12)

Br1—C15	1.896 (2)	C8—H8	0.9500
O1—C1	1.369 (3)	C9—C10	1.419 (3)
O1—C18	1.428 (3)	C10—C11	1.509 (3)
O2—C7	1.365 (3)	C11—C12	1.490 (3)
O2—C19	1.426 (3)	C12—C17	1.387 (3)
O3—C11	1.217 (3)	C12—C13	1.391 (3)
C1—C10	1.378 (3)	C13—C14	1.380 (3)
C1—C2	1.410 (3)	C13—H13	0.9500
C2—C3	1.363 (3)	C14—C15	1.375 (4)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.409 (3)	C15—C16	1.376 (3)
C3—H3	0.9500	C16—C17	1.381 (3)
C4—C5	1.413 (3)	C16—H16	0.9500
C4—C9	1.433 (3)	C17—H17	0.9500
C5—C6	1.363 (3)	C18—H18A	0.9800
C5—H5	0.9500	C18—H18B	0.9800
C6—C7	1.412 (3)	C18—H18C	0.9800
C6—H6	0.9500	C19—H19A	0.9800
C7—C8	1.371 (3)	C19—H19B	0.9800
C8—C9	1.414 (3)	C19—H19C	0.9800
C1—O1—C18	118.30 (18)	O3—C11—C10	120.55 (19)
C7—O2—C19	118.76 (19)	C12—C11—C10	118.10 (17)
O1—C1—C10	115.70 (18)	C17—C12—C13	118.9 (2)
O1—C1—C2	123.3 (2)	C17—C12—C11	122.02 (18)
C10—C1—C2	121.0 (2)	C13—C12—C11	119.05 (19)
C3—C2—C1	119.2 (2)	C14—C13—C12	120.5 (2)
C3—C2—H2	120.4	C14—C13—H13	119.7
C1—C2—H2	120.4	C12—C13—H13	119.7
C2—C3—C4	122.3 (2)	C15—C14—C13	119.2 (2)
C2—C3—H3	118.9	C15—C14—H14	120.4
C4—C3—H3	118.9	C13—C14—H14	120.4
C3—C4—C5	123.16 (19)	C14—C15—C16	121.6 (2)
C3—C4—C9	118.6 (2)	C14—C15—Br1	119.02 (17)
C5—C4—C9	118.2 (2)	C16—C15—Br1	119.40 (18)
C6—C5—C4	122.1 (2)	C15—C16—C17	118.9 (2)
C6—C5—H5	118.9	C15—C16—H16	120.6
C4—C5—H5	118.9	C17—C16—H16	120.6
C5—C6—C7	119.4 (2)	C16—C17—C12	120.88 (19)
C5—C6—H6	120.3	C16—C17—H17	119.6
C7—C6—H6	120.3	C12—C17—H17	119.6
O2—C7—C8	115.71 (19)	O1—C18—H18A	109.5
O2—C7—C6	123.7 (2)	O1—C18—H18B	109.5
C8—C7—C6	120.5 (2)	H18A—C18—H18B	109.5
C7—C8—C9	121.04 (19)	O1—C18—H18C	109.5
C7—C8—H8	119.5	H18A—C18—H18C	109.5
C9—C8—H8	119.5	H18B—C18—H18C	109.5
C8—C9—C10	122.95 (18)	O2—C19—H19A	109.5
C8—C9—C4	118.61 (19)	O2—C19—H19B	109.5
C10—C9—C4	118.44 (19)	H19A—C19—H19B	109.5
C1—C10—C9	120.52 (18)	O2—C19—H19C	109.5
C1—C10—C11	120.11 (19)	H19A—C19—H19C	109.5
C9—C10—C11	119.35 (18)	H19B—C19—H19C	109.5
O3—C11—C12	121.32 (18)
C18—O1—C1—C10	179.6 (2)	O1—C1—C10—C11	−4.8 (3)
C18—O1—C1—C2	−1.4 (3)	C2—C1—C10—C11	176.16 (19)
O1—C1—C2—C3	−179.1 (2)	C8—C9—C10—C1	−177.79 (19)
C10—C1—C2—C3	−0.1 (3)	C4—C9—C10—C1	3.1 (3)
C1—C2—C3—C4	1.6 (3)	C8—C9—C10—C11	3.8 (3)
C2—C3—C4—C5	179.9 (2)	C4—C9—C10—C11	−175.36 (18)
C2—C3—C4—C9	−0.7 (3)	C1—C10—C11—O3	111.3 (2)
C3—C4—C5—C6	179.9 (2)	C9—C10—C11—O3	−70.3 (3)
C9—C4—C5—C6	0.5 (3)	C1—C10—C11—C12	−70.8 (3)
C4—C5—C6—C7	0.2 (3)	C9—C10—C11—C12	107.6 (2)
C19—O2—C7—C8	176.4 (2)	O3—C11—C12—C17	176.3 (2)
C19—O2—C7—C6	−4.0 (3)	C10—C11—C12—C17	−1.6 (3)
C5—C6—C7—O2	−179.7 (2)	O3—C11—C12—C13	−2.5 (3)
C5—C6—C7—C8	−0.1 (3)	C10—C11—C12—C13	179.6 (2)
O2—C7—C8—C9	178.88 (18)	C17—C12—C13—C14	1.2 (4)
C6—C7—C8—C9	−0.7 (3)	C11—C12—C13—C14	−179.9 (2)
C7—C8—C9—C10	−177.67 (19)	C12—C13—C14—C15	−0.1 (4)
C7—C8—C9—C4	1.4 (3)	C13—C14—C15—C16	−0.7 (4)
C3—C4—C9—C8	179.24 (18)	C13—C14—C15—Br1	178.6 (2)
C5—C4—C9—C8	−1.3 (3)	C14—C15—C16—C17	0.3 (4)
C3—C4—C9—C10	−1.6 (3)	Br1—C15—C16—C17	−178.97 (17)
C5—C4—C9—C10	177.83 (18)	C15—C16—C17—C12	0.9 (3)
O1—C1—C10—C9	176.75 (18)	C13—C12—C17—C16	−1.6 (3)
C2—C1—C10—C9	−2.3 (3)	C11—C12—C17—C16	179.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.95	2.57	3.372 (3)	142
C17—H17···O2ii	0.95	2.57	3.407 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.95	2.57	3.372 (3)	142
C17—H17⋯O2ii	0.95	2.57	3.407 (3)	148

Symmetry codes: (i) ; (ii) .