(8-Bromo-2,7-dimeth-oxy-1-naphth-yl)(4-chloro-phenyl)methanone.

In the title compound, C(19)H(14)BrClO(3), the naphthalene ring system and the benzene ring make a dihedral angle of 77.36 (10)°. The conformation around the central C=O group is such that the C=O bond vector forms a larger angle to the plane of the naphthalene ring system than to the plane of the benzene ring, viz. 75.73 (15)° versus 2.33 (17)°. In the crystal structure, a π-π inter-action is formed between naphthalene ring systems, with a centroid-centroid distance of 3.8363 (14) Å and a lateral offset of 1.606 Å. Inter-molecular C-H⋯Br and C-H⋯O hydrogen bonds and a C-H⋯π contact are present in the crystal structure.

Related literature

For the structures of closely related compounds, see: Mitsui et al. (2009 ▶, 2010 ▶); Mitsui, Nakaema, Noguchi, Okamoto & Yonezawa (2008 ▶); Mitsui, Nakaema, Noguchi & Yonezawa (2008 ▶).

Experimental

Crystal data

C19H14BrClO3

M = 405.66

Monoclinic,

a = 15.0867 (3) Å

b = 8.72313 (16) Å

c = 13.5894 (3) Å

β = 108.536 (1)°

V = 1695.64 (6) Å3

Z = 4

Cu Kα radiation

μ = 4.88 mm−1

T = 193 K

0.50 × 0.40 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.160, T max = 0.614

26838 measured reflections

3092 independent reflections

2845 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.086

S = 1.07

3092 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.43 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/S1600536810009463/is2530sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009463/is2530Isup2.hkl

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

C19H14BrClO3	F(000) = 816
Mr = 405.66	Dx = 1.589 Mg m−3
Monoclinic, P21/c	Melting point = 447.0–447.5 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54187 Å
a = 15.0867 (3) Å	Cell parameters from 25305 reflections
b = 8.72313 (16) Å	θ = 3.1–68.2°
c = 13.5894 (3) Å	µ = 4.88 mm−1
β = 108.536 (1)°	T = 193 K
V = 1695.64 (6) Å3	Platelet, colorless
Z = 4	0.50 × 0.40 × 0.20 mm

Rigaku R-AXIS RAPID diffractometer	3092 independent reflections
Radiation source: rotating anode	2845 reflections with I > 2σ(I)
graphite	Rint = 0.071
Detector resolution: 10.00 pixels mm-1	θmax = 68.2°, θmin = 3.1°
ω scans	h = −18→18
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −10→10
Tmin = 0.160, Tmax = 0.614	l = −16→15
26838 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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.036P)2 + 0.9139P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
3092 reflections	Δρmax = 0.45 e Å−3
220 parameters	Δρmin = −0.43 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: 0.0034 (2)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.147755 (18)	0.22446 (3)	0.41929 (2)	0.03662 (13)
Cl1	0.50868 (6)	0.13053 (10)	0.23975 (8)	0.0709 (3)
O1	0.14525 (10)	0.53370 (19)	0.27564 (12)	0.0318 (4)
O2	0.32367 (14)	0.7494 (2)	0.39704 (16)	0.0411 (5)
O3	0.03824 (12)	0.2074 (2)	0.55691 (15)	0.0372 (4)
C1	0.23238 (14)	0.5731 (2)	0.44962 (17)	0.0248 (5)
C2	0.27916 (16)	0.7120 (3)	0.4674 (2)	0.0307 (5)
C3	0.27780 (19)	0.8080 (3)	0.5498 (2)	0.0401 (6)
H3	0.3116	0.9017	0.5619	0.048*
C4	0.2273 (2)	0.7647 (3)	0.6119 (2)	0.0417 (6)
H4	0.2251	0.8309	0.6666	0.050*
C5	0.17794 (16)	0.6246 (3)	0.59797 (19)	0.0313 (5)
C6	0.12237 (18)	0.5854 (3)	0.66060 (19)	0.0375 (6)
H6	0.1192	0.6544	0.7135	0.045*
C7	0.07338 (16)	0.4519 (3)	0.64755 (19)	0.0339 (6)
H7	0.0346	0.4304	0.6889	0.041*
C8	0.08055 (15)	0.3461 (3)	0.57235 (18)	0.0294 (5)
C9	0.13469 (15)	0.3817 (3)	0.51018 (17)	0.0253 (5)
C10	0.18258 (14)	0.5234 (2)	0.51737 (16)	0.0243 (5)
C11	0.21803 (15)	0.5047 (2)	0.34374 (17)	0.0251 (5)
C12	0.29276 (15)	0.4137 (2)	0.32081 (18)	0.0264 (5)
C13	0.37831 (16)	0.3841 (3)	0.39620 (19)	0.0325 (5)
H13	0.3907	0.4235	0.4644	0.039*
C14	0.44561 (17)	0.2970 (3)	0.3718 (2)	0.0406 (6)
H14	0.5043	0.2775	0.4228	0.049*
C15	0.42620 (18)	0.2396 (3)	0.2732 (2)	0.0402 (7)
C16	0.34149 (19)	0.2680 (3)	0.1967 (2)	0.0397 (6)
H16	0.3294	0.2279	0.1287	0.048*
C17	0.27547 (16)	0.3553 (3)	0.22136 (19)	0.0321 (5)
H17	0.2174	0.3758	0.1697	0.039*
C18	0.3499 (2)	0.9051 (3)	0.3903 (3)	0.0476 (7)
H18A	0.3716	0.9176	0.3300	0.057*
H18B	0.4004	0.9329	0.4535	0.057*
H18C	0.2959	0.9718	0.3827	0.057*
C19	−0.01877 (17)	0.1655 (3)	0.6194 (2)	0.0425 (7)
H19A	−0.0466	0.0645	0.5978	0.051*
H19B	−0.0685	0.2416	0.6104	0.051*
H19C	0.0199	0.1618	0.6925	0.051*

	U11	U22	U33	U12	U13	U23
Br1	0.05100 (19)	0.02421 (18)	0.0425 (2)	−0.00965 (10)	0.02598 (14)	−0.00643 (10)
Cl1	0.0531 (4)	0.0667 (5)	0.1010 (7)	0.0177 (4)	0.0360 (4)	−0.0234 (5)
O1	0.0301 (8)	0.0363 (9)	0.0288 (9)	0.0025 (7)	0.0094 (7)	0.0005 (7)
O2	0.0518 (11)	0.0298 (9)	0.0537 (13)	−0.0136 (8)	0.0336 (10)	−0.0043 (8)
O3	0.0405 (9)	0.0338 (10)	0.0443 (11)	−0.0086 (7)	0.0236 (8)	0.0042 (8)
C1	0.0244 (10)	0.0233 (11)	0.0284 (12)	0.0000 (8)	0.0108 (9)	−0.0009 (9)
C2	0.0310 (11)	0.0301 (13)	0.0351 (14)	−0.0043 (9)	0.0163 (10)	−0.0003 (10)
C3	0.0476 (14)	0.0312 (13)	0.0453 (16)	−0.0136 (11)	0.0201 (12)	−0.0121 (12)
C4	0.0554 (16)	0.0370 (14)	0.0369 (15)	−0.0104 (12)	0.0207 (13)	−0.0157 (12)
C5	0.0358 (12)	0.0307 (12)	0.0296 (13)	−0.0025 (10)	0.0136 (10)	−0.0030 (10)
C6	0.0471 (14)	0.0396 (14)	0.0305 (14)	0.0011 (11)	0.0191 (11)	−0.0049 (11)
C7	0.0357 (12)	0.0410 (14)	0.0314 (13)	0.0029 (10)	0.0194 (10)	0.0055 (11)
C8	0.0280 (10)	0.0283 (12)	0.0322 (13)	0.0015 (9)	0.0099 (9)	0.0075 (10)
C9	0.0287 (10)	0.0252 (11)	0.0233 (11)	0.0003 (9)	0.0100 (9)	0.0009 (9)
C10	0.0248 (10)	0.0241 (11)	0.0236 (11)	0.0006 (8)	0.0069 (8)	0.0017 (9)
C11	0.0297 (11)	0.0209 (11)	0.0276 (12)	−0.0044 (8)	0.0131 (9)	0.0029 (9)
C12	0.0293 (11)	0.0219 (11)	0.0324 (13)	−0.0019 (8)	0.0160 (9)	0.0009 (9)
C13	0.0356 (12)	0.0310 (12)	0.0316 (13)	−0.0006 (10)	0.0116 (10)	0.0012 (10)
C14	0.0308 (12)	0.0351 (14)	0.0541 (17)	0.0055 (10)	0.0110 (12)	0.0050 (13)
C15	0.0366 (13)	0.0287 (13)	0.062 (2)	0.0007 (10)	0.0258 (13)	−0.0069 (12)
C16	0.0423 (14)	0.0349 (14)	0.0468 (17)	−0.0038 (11)	0.0212 (13)	−0.0119 (12)
C17	0.0338 (11)	0.0291 (12)	0.0357 (14)	−0.0050 (9)	0.0142 (10)	−0.0047 (10)
C18	0.0543 (16)	0.0321 (14)	0.0622 (19)	−0.0114 (12)	0.0269 (14)	0.0052 (13)
C19	0.0357 (13)	0.0438 (16)	0.0538 (17)	−0.0021 (11)	0.0223 (12)	0.0171 (14)

Br1—C9	1.898 (2)	C7—H7	0.9500
Cl1—C15	1.738 (3)	C8—C9	1.384 (3)
O1—C11	1.217 (3)	C9—C10	1.419 (3)
O2—C2	1.371 (3)	C11—C12	1.490 (3)
O2—C18	1.426 (3)	C12—C17	1.389 (3)
O3—C8	1.353 (3)	C12—C13	1.393 (3)
O3—C19	1.435 (3)	C13—C14	1.390 (4)
C1—C2	1.385 (3)	C13—H13	0.9500
C1—C10	1.428 (3)	C14—C15	1.372 (4)
C1—C11	1.508 (3)	C14—H14	0.9500
C2—C3	1.403 (4)	C15—C16	1.389 (4)
C3—C4	1.359 (4)	C16—C17	1.377 (3)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.412 (3)	C17—H17	0.9500
C4—H4	0.9500	C18—H18A	0.9800
C5—C6	1.414 (3)	C18—H18B	0.9800
C5—C10	1.426 (3)	C18—H18C	0.9800
C6—C7	1.360 (4)	C19—H19A	0.9800
C6—H6	0.9500	C19—H19B	0.9800
C7—C8	1.406 (4)	C19—H19C	0.9800
C2—O2—C18	118.6 (2)	O1—C11—C1	117.7 (2)
C8—O3—C19	118.6 (2)	C12—C11—C1	121.43 (18)
C2—C1—C10	119.8 (2)	C17—C12—C13	119.4 (2)
C2—C1—C11	115.1 (2)	C17—C12—C11	118.6 (2)
C10—C1—C11	123.34 (18)	C13—C12—C11	122.0 (2)
O2—C2—C1	114.9 (2)	C14—C13—C12	120.2 (2)
O2—C2—C3	123.3 (2)	C14—C13—H13	119.9
C1—C2—C3	121.7 (2)	C12—C13—H13	119.9
C4—C3—C2	118.9 (2)	C15—C14—C13	119.1 (2)
C4—C3—H3	120.5	C15—C14—H14	120.4
C2—C3—H3	120.5	C13—C14—H14	120.4
C3—C4—C5	122.2 (3)	C14—C15—C16	121.7 (2)
C3—C4—H4	118.9	C14—C15—Cl1	120.5 (2)
C5—C4—H4	118.9	C16—C15—Cl1	117.8 (2)
C4—C5—C6	121.1 (2)	C17—C16—C15	118.8 (3)
C4—C5—C10	119.1 (2)	C17—C16—H16	120.6
C6—C5—C10	119.7 (2)	C15—C16—H16	120.6
C7—C6—C5	122.0 (2)	C16—C17—C12	120.8 (2)
C7—C6—H6	119.0	C16—C17—H17	119.6
C5—C6—H6	119.0	C12—C17—H17	119.6
C6—C7—C8	119.5 (2)	O2—C18—H18A	109.5
C6—C7—H7	120.3	O2—C18—H18B	109.5
C8—C7—H7	120.3	H18A—C18—H18B	109.5
O3—C8—C9	116.5 (2)	O2—C18—H18C	109.5
O3—C8—C7	123.9 (2)	H18A—C18—H18C	109.5
C9—C8—C7	119.5 (2)	H18B—C18—H18C	109.5
C8—C9—C10	122.6 (2)	O3—C19—H19A	109.5
C8—C9—Br1	116.03 (17)	O3—C19—H19B	109.5
C10—C9—Br1	121.22 (17)	H19A—C19—H19B	109.5
C9—C10—C5	116.3 (2)	O3—C19—H19C	109.5
C9—C10—C1	125.5 (2)	H19A—C19—H19C	109.5
C5—C10—C1	118.2 (2)	H19B—C19—H19C	109.5
O1—C11—C12	120.8 (2)
C18—O2—C2—C1	162.1 (2)	C4—C5—C10—C9	177.4 (2)
C18—O2—C2—C3	−16.0 (4)	C6—C5—C10—C9	−4.2 (3)
C10—C1—C2—O2	−179.2 (2)	C4—C5—C10—C1	−4.0 (3)
C11—C1—C2—O2	−14.2 (3)	C6—C5—C10—C1	174.3 (2)
C10—C1—C2—C3	−1.2 (3)	C2—C1—C10—C9	−177.6 (2)
C11—C1—C2—C3	163.9 (2)	C11—C1—C10—C9	18.6 (3)
O2—C2—C3—C4	176.3 (3)	C2—C1—C10—C5	4.0 (3)
C1—C2—C3—C4	−1.6 (4)	C11—C1—C10—C5	−159.8 (2)
C2—C3—C4—C5	1.6 (4)	C2—C1—C11—O1	−92.9 (3)
C3—C4—C5—C6	−177.0 (3)	C10—C1—C11—O1	71.6 (3)
C3—C4—C5—C10	1.3 (4)	C2—C1—C11—C12	82.9 (3)
C4—C5—C6—C7	179.2 (3)	C10—C1—C11—C12	−112.7 (2)
C10—C5—C6—C7	0.9 (4)	O1—C11—C12—C17	−3.6 (3)
C5—C6—C7—C8	2.5 (4)	C1—C11—C12—C17	−179.3 (2)
C19—O3—C8—C9	−179.9 (2)	O1—C11—C12—C13	177.3 (2)
C19—O3—C8—C7	1.1 (3)	C1—C11—C12—C13	1.6 (3)
C6—C7—C8—O3	176.7 (2)	C17—C12—C13—C14	0.1 (4)
C6—C7—C8—C9	−2.3 (3)	C11—C12—C13—C14	179.2 (2)
O3—C8—C9—C10	179.58 (19)	C12—C13—C14—C15	−0.7 (4)
C7—C8—C9—C10	−1.3 (3)	C13—C14—C15—C16	0.9 (4)
O3—C8—C9—Br1	−4.0 (3)	C13—C14—C15—Cl1	179.9 (2)
C7—C8—C9—Br1	175.04 (16)	C14—C15—C16—C17	−0.4 (4)
C8—C9—C10—C5	4.5 (3)	Cl1—C15—C16—C17	−179.43 (19)
Br1—C9—C10—C5	−171.66 (16)	C15—C16—C17—C12	−0.2 (4)
C8—C9—C10—C1	−173.9 (2)	C13—C12—C17—C16	0.4 (4)
Br1—C9—C10—C1	9.9 (3)	C11—C12—C17—C16	−178.7 (2)

Cg1 is the centroid of the C1–C5/C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1i	0.95	2.49	3.366 (3)	154
C19—H19A···Br1ii	0.98	2.92	3.871 (3)	165
C19—H19C···O1iii	0.98	2.53	3.211 (3)	126
C19—H19B···Cg1iv	0.98	2.70	3.509 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C5/C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1i	0.95	2.49	3.366 (3)	154
C19—H19A⋯Br1ii	0.98	2.92	3.871 (3)	165
C19—H19C⋯O1iii	0.98	2.53	3.211 (3)	126
C19—H19B⋯Cg1iv	0.98	2.70	3.509 (3)	140

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .