(4-Bromo-phen-yl)(3,6-dimeth-oxy-2-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 62.51 (8)°. The bridging carbonyl C-C(=O)-C plane makes dihedral angles of 47.07 (6)° with the naphthalene ring system and 24.20 (10)° with the benzene ring. A weak inter-molecular C-H⋯O hydrogen bond exists between the H atom of one meth-oxy group and the O atom of the other meth-oxy group in an adjacent mol-ecule. The crystal packing is additionally stabilized by two types of weak inter-molecular inter-actions involving the Br atom, C-H⋯Br and Br⋯O [3.2802 (14) Å].

Related literature

For electrophilic aromatic substitution of naphthalene deriv­atives affording peri-aroylated compounds regioselectively, see: Okamoto & Yonezawa (2009 ▶). For the structures of closely related compounds, see: Kato et al. (2010 ▶); Muto et al. (2010 ▶); Nakaema et al. (2008 ▶); Watanabe et al. (2010a ▶,b ▶).

Experimental

Crystal data

C19H15BrO3

M = 371.22

Monoclinic,

a = 7.88917 (14) Å

b = 21.0182 (4) Å

c = 10.06272 (18) Å

β = 105.971 (1)°

V = 1604.16 (5) Å3

Z = 4

Cu Kα radiation

μ = 3.60 mm−1

T = 193 K

0.60 × 0.40 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

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

29541 measured reflections

2934 independent reflections

2767 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.086

S = 1.12

2934 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −1.03 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 I, global. DOI: 10.1107/S160053681004016X/vm2049sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004016X/vm2049Isup2.hkl

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

C19H15BrO3	F(000) = 752
Mr = 371.22	Dx = 1.537 Mg m−3
Monoclinic, P21/c	Melting point = 416.9–419.5 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54187 Å
a = 7.88917 (14) Å	Cell parameters from 26572 reflections
b = 21.0182 (4) Å	θ = 4.2–68.3°
c = 10.06272 (18) Å	µ = 3.60 mm−1
β = 105.971 (1)°	T = 193 K
V = 1604.16 (5) Å3	Platelet, colorless
Z = 4	0.60 × 0.40 × 0.20 mm

Rigaku R-AXIS RAPID diffractometer	2934 independent reflections
Radiation source: rotating anode	2767 reflections with I > 2σ(I)
graphite	Rint = 0.044
Detector resolution: 10.00 pixels mm-1	θmax = 68.3°, θmin = 4.2°
ω scans	h = −9→9
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −25→25
Tmin = 0.161, Tmax = 0.533	l = −12→12
29541 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0497P)2 + 0.6344P] where P = (Fo2 + 2Fc2)/3
2934 reflections	(Δ/σ)max < 0.001
210 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −1.02 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	0.24719 (3)	0.056869 (10)	0.494126 (19)	0.03961 (11)
O1	−0.46425 (17)	0.28009 (7)	−0.69867 (14)	0.0406 (3)
O2	0.20106 (17)	0.19970 (6)	−0.05734 (13)	0.0342 (3)
O3	0.24997 (19)	0.03129 (7)	−0.18371 (14)	0.0405 (3)
C1	−0.3611 (2)	0.24042 (10)	−0.6033 (2)	0.0324 (4)
C2	−0.3738 (3)	0.17558 (10)	−0.6441 (2)	0.0384 (4)
H2	−0.4485	0.1636	−0.7292	0.046*
C3	−0.2762 (3)	0.13090 (10)	−0.5582 (2)	0.0375 (4)
H3	−0.2853	0.0885	−0.5854	0.045*
C4	−0.1608 (2)	0.14784 (9)	−0.4282 (2)	0.0302 (4)
C5	−0.0537 (2)	0.10319 (9)	−0.33881 (19)	0.0303 (4)
H5	−0.0616	0.0605	−0.3643	0.036*
C6	0.0620 (2)	0.12056 (9)	−0.21526 (18)	0.0284 (4)
C7	0.0759 (2)	0.18618 (9)	−0.17702 (18)	0.0279 (4)
C8	−0.0283 (2)	0.23056 (9)	−0.26096 (19)	0.0284 (4)
H8	−0.0198	0.2730	−0.2340	0.034*
C9	−0.1488 (2)	0.21296 (9)	−0.38808 (19)	0.0278 (4)
C10	−0.2524 (2)	0.25890 (10)	−0.47798 (19)	0.0303 (4)
H10	−0.2466	0.3015	−0.4520	0.036*
C11	0.1740 (2)	0.06982 (9)	−0.1299 (2)	0.0308 (4)
C12	0.1884 (2)	0.06594 (8)	0.02077 (19)	0.0291 (4)
C13	0.0583 (2)	0.09052 (9)	0.0753 (2)	0.0349 (4)
H13	−0.0401	0.1100	0.0169	0.042*
C14	0.0731 (3)	0.08652 (9)	0.2154 (2)	0.0363 (4)
H14	−0.0155	0.1024	0.2509	0.044*
C15	0.2217 (3)	0.05857 (8)	0.3014 (2)	0.0312 (4)
C16	0.3515 (3)	0.03239 (10)	0.2499 (2)	0.0370 (4)
H16	0.4493	0.0127	0.3087	0.044*
C17	0.3339 (3)	0.03590 (10)	0.1099 (2)	0.0358 (4)
H17	0.4200	0.0180	0.0743	0.043*
C18	−0.4465 (3)	0.34656 (10)	−0.6723 (2)	0.0454 (5)
H18A	−0.5287	0.3692	−0.7451	0.055*
H18B	−0.3286	0.3596	−0.6683	0.055*
H18C	−0.4704	0.3558	−0.5857	0.055*
C19	0.2347 (2)	0.26549 (10)	−0.0224 (2)	0.0348 (4)
H19A	0.3294	0.2689	0.0609	0.042*
H19B	0.1305	0.2847	−0.0086	0.042*
H19C	0.2667	0.2869	−0.0962	0.042*

	U11	U22	U33	U12	U13	U23
Br1	0.05907 (18)	0.03269 (17)	0.02418 (16)	0.00179 (8)	0.00659 (11)	−0.00036 (7)
O1	0.0367 (7)	0.0454 (8)	0.0321 (7)	0.0022 (6)	−0.0032 (6)	0.0083 (6)
O2	0.0389 (7)	0.0309 (7)	0.0260 (7)	0.0006 (5)	−0.0024 (5)	−0.0014 (5)
O3	0.0488 (8)	0.0407 (8)	0.0321 (7)	0.0134 (6)	0.0113 (6)	−0.0007 (6)
C1	0.0269 (8)	0.0411 (11)	0.0274 (9)	0.0000 (7)	0.0044 (7)	0.0071 (8)
C2	0.0370 (9)	0.0451 (12)	0.0269 (10)	−0.0061 (8)	−0.0017 (8)	0.0000 (8)
C3	0.0399 (10)	0.0365 (11)	0.0309 (11)	−0.0069 (8)	0.0011 (8)	−0.0009 (9)
C4	0.0301 (8)	0.0321 (10)	0.0278 (9)	−0.0050 (7)	0.0071 (7)	0.0003 (7)
C5	0.0353 (9)	0.0280 (9)	0.0272 (9)	−0.0032 (7)	0.0077 (7)	−0.0001 (7)
C6	0.0310 (8)	0.0298 (9)	0.0248 (9)	0.0001 (7)	0.0083 (7)	0.0030 (7)
C7	0.0287 (8)	0.0325 (9)	0.0216 (8)	−0.0019 (7)	0.0055 (6)	−0.0005 (7)
C8	0.0308 (8)	0.0271 (9)	0.0263 (9)	−0.0003 (7)	0.0066 (7)	−0.0001 (7)
C9	0.0261 (8)	0.0320 (10)	0.0260 (9)	−0.0010 (7)	0.0083 (7)	0.0028 (7)
C10	0.0298 (9)	0.0326 (10)	0.0282 (9)	−0.0004 (7)	0.0074 (7)	0.0036 (7)
C11	0.0324 (9)	0.0292 (9)	0.0292 (10)	0.0004 (7)	0.0060 (7)	0.0010 (8)
C12	0.0331 (9)	0.0248 (9)	0.0282 (10)	0.0013 (7)	0.0063 (7)	0.0023 (7)
C13	0.0339 (9)	0.0383 (10)	0.0311 (10)	0.0102 (8)	0.0067 (8)	0.0084 (8)
C14	0.0404 (10)	0.0361 (10)	0.0337 (10)	0.0087 (8)	0.0123 (8)	0.0054 (8)
C15	0.0427 (10)	0.0243 (9)	0.0246 (9)	−0.0018 (7)	0.0059 (8)	0.0015 (7)
C16	0.0371 (9)	0.0375 (11)	0.0313 (10)	0.0092 (8)	0.0006 (8)	0.0032 (8)
C17	0.0358 (9)	0.0372 (11)	0.0335 (10)	0.0107 (8)	0.0081 (8)	0.0030 (9)
C18	0.0429 (11)	0.0452 (12)	0.0415 (12)	0.0071 (9)	0.0004 (9)	0.0127 (10)
C19	0.0362 (9)	0.0335 (11)	0.0304 (9)	−0.0010 (7)	0.0019 (8)	−0.0052 (8)

Br1—C15	1.8942 (19)	C8—H8	0.9300
O1—C1	1.359 (2)	C9—C10	1.418 (3)
O1—C18	1.422 (3)	C10—H10	0.9300
O2—C7	1.361 (2)	C11—C12	1.491 (3)
O2—C19	1.433 (2)	C12—C13	1.390 (3)
O3—C11	1.219 (2)	C12—C17	1.398 (3)
C1—C10	1.372 (3)	C13—C14	1.384 (3)
C1—C2	1.419 (3)	C13—H13	0.9300
C2—C3	1.362 (3)	C14—C15	1.383 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.419 (3)	C15—C16	1.383 (3)
C3—H3	0.9300	C16—C17	1.379 (3)
C4—C5	1.409 (3)	C16—H16	0.9300
C4—C9	1.423 (3)	C17—H17	0.9300
C5—C6	1.374 (3)	C18—H18A	0.9600
C5—H5	0.9300	C18—H18B	0.9600
C6—C7	1.428 (3)	C18—H18C	0.9600
C6—C11	1.496 (3)	C19—H19A	0.9600
C7—C8	1.370 (3)	C19—H19B	0.9600
C8—C9	1.417 (2)	C19—H19C	0.9600
C1—O1—C18	117.51 (15)	O3—C11—C6	120.23 (18)
C7—O2—C19	117.30 (14)	C12—C11—C6	119.37 (16)
O1—C1—C10	125.22 (19)	C13—C12—C17	118.65 (18)
O1—C1—C2	113.82 (17)	C13—C12—C11	121.55 (16)
C10—C1—C2	120.96 (17)	C17—C12—C11	119.78 (17)
C3—C2—C1	119.73 (18)	C14—C13—C12	121.02 (17)
C3—C2—H2	120.1	C14—C13—H13	119.5
C1—C2—H2	120.1	C12—C13—H13	119.5
C2—C3—C4	121.30 (19)	C15—C14—C13	118.84 (18)
C2—C3—H3	119.4	C15—C14—H14	120.6
C4—C3—H3	119.4	C13—C14—H14	120.6
C5—C4—C3	122.78 (18)	C14—C15—C16	121.49 (18)
C5—C4—C9	118.58 (16)	C14—C15—Br1	118.80 (15)
C3—C4—C9	118.61 (17)	C16—C15—Br1	119.71 (14)
C6—C5—C4	122.20 (17)	C17—C16—C15	119.00 (17)
C6—C5—H5	118.9	C17—C16—H16	120.5
C4—C5—H5	118.9	C15—C16—H16	120.5
C5—C6—C7	118.89 (16)	C16—C17—C12	120.94 (18)
C5—C6—C11	118.06 (17)	C16—C17—H17	119.5
C7—C6—C11	122.98 (16)	C12—C17—H17	119.5
O2—C7—C8	124.72 (16)	O1—C18—H18A	109.5
O2—C7—C6	115.05 (15)	O1—C18—H18B	109.5
C8—C7—C6	120.19 (16)	H18A—C18—H18B	109.5
C7—C8—C9	121.22 (17)	O1—C18—H18C	109.5
C7—C8—H8	119.4	H18A—C18—H18C	109.5
C9—C8—H8	119.4	H18B—C18—H18C	109.5
C8—C9—C10	121.58 (18)	O2—C19—H19A	109.5
C8—C9—C4	118.88 (16)	O2—C19—H19B	109.5
C10—C9—C4	119.50 (17)	H19A—C19—H19B	109.5
C1—C10—C9	119.90 (19)	O2—C19—H19C	109.5
C1—C10—H10	120.1	H19A—C19—H19C	109.5
C9—C10—H10	120.1	H19B—C19—H19C	109.5
O3—C11—C12	120.38 (17)
C18—O1—C1—C10	6.0 (3)	C3—C4—C9—C10	0.4 (3)
C18—O1—C1—C2	−173.88 (17)	O1—C1—C10—C9	−178.98 (17)
O1—C1—C2—C3	179.56 (18)	C2—C1—C10—C9	0.9 (3)
C10—C1—C2—C3	−0.3 (3)	C8—C9—C10—C1	176.76 (17)
C1—C2—C3—C4	−0.2 (3)	C4—C9—C10—C1	−0.9 (2)
C2—C3—C4—C5	−177.87 (19)	C5—C6—C11—O3	46.0 (3)
C2—C3—C4—C9	0.2 (3)	C7—C6—C11—O3	−131.1 (2)
C3—C4—C5—C6	177.68 (18)	C5—C6—C11—C12	−132.63 (18)
C9—C4—C5—C6	−0.3 (3)	C7—C6—C11—C12	50.3 (2)
C4—C5—C6—C7	−0.9 (3)	O3—C11—C12—C13	−154.64 (19)
C4—C5—C6—C11	−178.08 (17)	C6—C11—C12—C13	24.0 (3)
C19—O2—C7—C8	−4.8 (2)	O3—C11—C12—C17	24.1 (3)
C19—O2—C7—C6	172.93 (15)	C6—C11—C12—C17	−157.30 (19)
C5—C6—C7—O2	−176.14 (16)	C17—C12—C13—C14	1.1 (3)
C11—C6—C7—O2	0.9 (2)	C11—C12—C13—C14	179.87 (18)
C5—C6—C7—C8	1.7 (3)	C12—C13—C14—C15	1.2 (3)
C11—C6—C7—C8	178.79 (16)	C13—C14—C15—C16	−2.7 (3)
O2—C7—C8—C9	176.31 (16)	C13—C14—C15—Br1	176.93 (15)
C6—C7—C8—C9	−1.4 (3)	C14—C15—C16—C17	1.8 (3)
C7—C8—C9—C10	−177.62 (16)	Br1—C15—C16—C17	−177.86 (15)
C7—C8—C9—C4	0.1 (3)	C15—C16—C17—C12	0.7 (3)
C5—C4—C9—C8	0.8 (3)	C13—C12—C17—C16	−2.1 (3)
C3—C4—C9—C8	−177.36 (17)	C11—C12—C17—C16	179.15 (19)
C5—C4—C9—C10	178.52 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···O1i	0.96	2.53	3.477 (2)	170
C5—H5···Brii	0.93	2.98	3.8441 (18)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19A⋯O1i	0.96	2.53	3.477 (2)	170
C5—H5⋯Brii	0.93	2.98	3.8441 (18)	155

Symmetry codes: (i) ; (ii) .