(4-Chloro-phen-yl)(3,8-dibromo-2-hydr-oxy-7-meth-oxy-1-naphth-yl)methanone.

In the title compound, C(18)H(11)Br(2)ClO(3), an intra-molecular O-H⋯O=C hydrogen bond occurs, forming a six-membered ring. The naphthalene ring system and the benzene ring make a dihedral angle of 57.36 (9)°. The central carbonyl C-(C=O)-C group is twisted away from the naphthalene ring system and the benzene ring by 18.61 (15) and 26.25 (16)°, respectively. In the crystal structure, two inter-molecular Br⋯Cl close contacts [3.4927 (7) and 3.4325 (7) Å] are observed.

Related literature

For related structures, see: Mitsui et al. (2009 ▶); Mitsui, Nakaema, Nagasawa et al. (2010 ▶); Mitsui, Nakaema, Noguchi, Okamoto & Yonezawa (2008 ▶); Mitsui, Nakaema, Noguchi & Yonezawa (2008 ▶); Mitsui, Nagasawa, Watanabe et al. (2010 ▶). For information on halogen⋯halogen contacts, see: Moorthy et al. (2002 ▶); Pedireddi et al. (1994 ▶); Saruma & Desiraju (1986 ▶).

Experimental

Crystal data

C18H11Br2ClO3

M = 470.54

Monoclinic,

a = 12.1513 (2) Å

b = 10.06343 (18) Å

c = 13.8936 (3) Å

β = 103.675 (1)°

V = 1650.79 (5) Å3

Z = 4

Cu Kα radiation

μ = 7.85 mm−1

T = 193 K

0.30 × 0.25 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.189, T max = 0.308

29373 measured reflections

3022 independent reflections

2940 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.076

S = 1.11

3022 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.64 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/S1600536810015527/is2542sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015527/is2542Isup2.hkl

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

C18H11Br2ClO3	F(000) = 920
Mr = 470.54	Dx = 1.893 Mg m−3
Monoclinic, P21/c	Melting point = 455.0–455.5 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54187 Å
a = 12.1513 (2) Å	Cell parameters from 28732 reflections
b = 10.06343 (18) Å	θ = 3.3–68.2°
c = 13.8936 (3) Å	µ = 7.85 mm−1
β = 103.675 (1)°	T = 193 K
V = 1650.79 (5) Å3	Block, yellow
Z = 4	0.30 × 0.25 × 0.20 mm

Rigaku R-AXIS RAPID diffractometer	3022 independent reflections
Radiation source: rotating anode	2940 reflections with I > 2σ(I)
graphite	Rint = 0.068
Detector resolution: 10.00 pixels mm-1	θmax = 68.3°, θmin = 3.7°
ω scans	h = −14→14
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −12→12
Tmin = 0.189, Tmax = 0.308	l = −16→16
29373 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)] = 0.028	H-atom parameters constrained
wR(F2) = 0.076	w = 1/[σ2(Fo2) + (0.0457P)2 + 0.9314P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
3022 reflections	Δρmax = 0.60 e Å−3
219 parameters	Δρmin = −0.64 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: 0.0162 (4)

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	0.348845 (18)	0.93221 (2)	0.140206 (18)	0.02724 (13)
Br2	−0.250748 (19)	0.77531 (3)	0.077383 (18)	0.03487 (13)
Cl1	0.49341 (5)	0.85290 (6)	0.59621 (4)	0.03239 (17)
O1	0.18770 (16)	0.61119 (18)	0.17108 (14)	0.0377 (4)
O2	−0.02937 (15)	0.63660 (18)	0.11024 (13)	0.0357 (4)
H2O	0.0329	0.5982	0.1198	0.043*
O3	0.33774 (13)	1.21262 (15)	0.17994 (12)	0.0256 (3)
C1	0.09899 (18)	0.8215 (2)	0.14949 (15)	0.0222 (4)
C2	−0.0097 (2)	0.7676 (2)	0.11910 (17)	0.0264 (5)
C3	−0.10526 (18)	0.8529 (3)	0.10204 (16)	0.0268 (5)
C4	−0.09270 (18)	0.9868 (3)	0.10944 (16)	0.0268 (5)
H4	−0.1579	1.0417	0.1004	0.032*
C5	0.01632 (18)	1.0458 (2)	0.13047 (16)	0.0232 (5)
C6	0.02945 (19)	1.1856 (2)	0.13389 (17)	0.0266 (5)
H6	−0.0361	1.2402	0.1217	0.032*
C7	0.1339 (2)	1.2440 (2)	0.15434 (17)	0.0259 (5)
H7	0.1408	1.3377	0.1617	0.031*
C8	0.23139 (18)	1.1645 (2)	0.16441 (15)	0.0216 (4)
C9	0.21941 (17)	1.0276 (2)	0.15487 (15)	0.0198 (4)
C10	0.11426 (18)	0.9635 (2)	0.14633 (15)	0.0203 (4)
C11	0.18698 (19)	0.7270 (2)	0.20076 (17)	0.0249 (5)
C12	0.26347 (18)	0.7639 (2)	0.29783 (17)	0.0229 (5)
C13	0.23528 (18)	0.8631 (2)	0.35778 (16)	0.0238 (5)
H13	0.1678	0.9131	0.3351	0.029*
C14	0.30470 (19)	0.8895 (2)	0.45010 (17)	0.0261 (5)
H14	0.2846	0.9559	0.4914	0.031*
C15	0.40403 (18)	0.8174 (2)	0.48129 (16)	0.0242 (5)
C16	0.43420 (19)	0.7176 (2)	0.42328 (18)	0.0278 (5)
H16	0.5024	0.6689	0.4458	0.033*
C17	0.36288 (19)	0.6908 (2)	0.33217 (18)	0.0268 (5)
H17	0.3816	0.6217	0.2922	0.032*
C18	0.3525 (2)	1.3542 (2)	0.18675 (19)	0.0318 (5)
H18A	0.4326	1.3760	0.1936	0.038*
H18B	0.3279	1.3873	0.2446	0.038*
H18C	0.3071	1.3960	0.1267	0.038*

	U11	U22	U33	U12	U13	U23
Br1	0.01855 (17)	0.02555 (19)	0.04042 (19)	0.00433 (8)	0.01259 (11)	0.00170 (9)
Br2	0.01849 (17)	0.0547 (2)	0.02984 (18)	−0.01184 (10)	0.00254 (11)	0.00019 (10)
Cl1	0.0229 (3)	0.0404 (4)	0.0307 (3)	−0.0019 (2)	0.0000 (2)	−0.0010 (2)
O1	0.0354 (10)	0.0239 (9)	0.0482 (11)	0.0019 (7)	−0.0014 (8)	−0.0083 (8)
O2	0.0278 (9)	0.0311 (10)	0.0447 (10)	−0.0081 (7)	0.0016 (7)	−0.0024 (8)
O3	0.0196 (8)	0.0220 (8)	0.0346 (9)	−0.0022 (6)	0.0050 (6)	−0.0014 (6)
C1	0.0185 (10)	0.0247 (12)	0.0229 (10)	−0.0011 (9)	0.0038 (8)	−0.0019 (8)
C2	0.0249 (12)	0.0304 (13)	0.0228 (11)	−0.0053 (9)	0.0034 (9)	−0.0009 (9)
C3	0.0150 (10)	0.0423 (14)	0.0219 (10)	−0.0054 (9)	0.0021 (8)	0.0000 (9)
C4	0.0175 (10)	0.0387 (14)	0.0246 (11)	0.0029 (9)	0.0056 (8)	0.0001 (9)
C5	0.0175 (10)	0.0325 (12)	0.0198 (10)	0.0035 (9)	0.0050 (8)	0.0004 (9)
C6	0.0202 (11)	0.0305 (12)	0.0291 (11)	0.0085 (9)	0.0059 (9)	0.0008 (9)
C7	0.0259 (12)	0.0236 (12)	0.0277 (11)	0.0041 (9)	0.0054 (9)	−0.0021 (9)
C8	0.0194 (10)	0.0262 (12)	0.0193 (9)	−0.0001 (8)	0.0046 (8)	−0.0011 (8)
C9	0.0156 (10)	0.0228 (11)	0.0213 (10)	0.0045 (8)	0.0049 (8)	0.0003 (8)
C10	0.0180 (10)	0.0242 (11)	0.0181 (9)	0.0016 (8)	0.0033 (8)	−0.0017 (8)
C11	0.0216 (11)	0.0221 (12)	0.0309 (12)	−0.0018 (9)	0.0063 (9)	−0.0011 (9)
C12	0.0195 (10)	0.0206 (11)	0.0292 (11)	−0.0014 (8)	0.0072 (9)	0.0036 (8)
C13	0.0176 (10)	0.0246 (12)	0.0301 (11)	0.0014 (8)	0.0075 (9)	0.0034 (9)
C14	0.0224 (11)	0.0285 (12)	0.0282 (11)	0.0011 (9)	0.0077 (9)	0.0002 (9)
C15	0.0188 (10)	0.0283 (12)	0.0243 (10)	−0.0046 (9)	0.0031 (8)	0.0024 (9)
C16	0.0191 (11)	0.0291 (13)	0.0352 (12)	0.0035 (9)	0.0063 (9)	0.0051 (9)
C17	0.0235 (11)	0.0243 (12)	0.0333 (12)	0.0019 (9)	0.0079 (9)	−0.0004 (9)
C18	0.0331 (13)	0.0233 (12)	0.0387 (13)	−0.0066 (10)	0.0075 (10)	−0.0012 (10)

Br1—C9	1.894 (2)	C7—C8	1.408 (3)
Br2—C3	1.888 (2)	C7—H7	0.9500
Cl1—C15	1.743 (2)	C8—C9	1.388 (3)
O1—C11	1.237 (3)	C9—C10	1.411 (3)
O2—C2	1.340 (3)	C11—C12	1.492 (3)
O2—H2O	0.8326	C12—C13	1.394 (3)
O3—C8	1.349 (3)	C12—C17	1.398 (3)
O3—C18	1.437 (3)	C13—C14	1.384 (3)
C1—C2	1.398 (3)	C13—H13	0.9500
C1—C10	1.443 (3)	C14—C15	1.387 (3)
C1—C11	1.481 (3)	C14—H14	0.9500
C2—C3	1.418 (3)	C15—C16	1.390 (3)
C3—C4	1.357 (4)	C16—C17	1.381 (3)
C4—C5	1.418 (3)	C16—H16	0.9500
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.415 (3)	C18—H18A	0.9800
C5—C10	1.424 (3)	C18—H18B	0.9800
C6—C7	1.366 (3)	C18—H18C	0.9800
C6—H6	0.9500
C2—O2—H2O	107.9	C9—C10—C1	124.8 (2)
C8—O3—C18	117.81 (18)	C5—C10—C1	118.17 (19)
C2—C1—C10	119.6 (2)	O1—C11—C1	120.4 (2)
C2—C1—C11	114.8 (2)	O1—C11—C12	118.9 (2)
C10—C1—C11	124.52 (19)	C1—C11—C12	119.97 (19)
O2—C2—C1	123.0 (2)	C13—C12—C17	119.2 (2)
O2—C2—C3	117.3 (2)	C13—C12—C11	122.0 (2)
C1—C2—C3	119.6 (2)	C17—C12—C11	118.7 (2)
C4—C3—C2	121.0 (2)	C14—C13—C12	120.6 (2)
C4—C3—Br2	120.53 (18)	C14—C13—H13	119.7
C2—C3—Br2	118.32 (18)	C12—C13—H13	119.7
C3—C4—C5	121.0 (2)	C13—C14—C15	118.9 (2)
C3—C4—H4	119.5	C13—C14—H14	120.5
C5—C4—H4	119.5	C15—C14—H14	120.5
C6—C5—C4	121.0 (2)	C14—C15—C16	121.7 (2)
C6—C5—C10	119.3 (2)	C14—C15—Cl1	119.13 (18)
C4—C5—C10	119.6 (2)	C16—C15—Cl1	119.13 (18)
C7—C6—C5	121.8 (2)	C17—C16—C15	118.6 (2)
C7—C6—H6	119.1	C17—C16—H16	120.7
C5—C6—H6	119.1	C15—C16—H16	120.7
C6—C7—C8	119.6 (2)	C16—C17—C12	120.9 (2)
C6—C7—H7	120.2	C16—C17—H17	119.5
C8—C7—H7	120.2	C12—C17—H17	119.5
O3—C8—C9	116.51 (19)	O3—C18—H18A	109.5
O3—C8—C7	124.3 (2)	O3—C18—H18B	109.5
C9—C8—C7	119.2 (2)	H18A—C18—H18B	109.5
C8—C9—C10	122.30 (19)	O3—C18—H18C	109.5
C8—C9—Br1	116.24 (16)	H18A—C18—H18C	109.5
C10—C9—Br1	121.15 (17)	H18B—C18—H18C	109.5
C9—C10—C5	117.0 (2)
C10—C1—C2—O2	172.9 (2)	C6—C5—C10—C9	−6.2 (3)
C11—C1—C2—O2	−18.3 (3)	C4—C5—C10—C9	172.45 (18)
C10—C1—C2—C3	−10.9 (3)	C6—C5—C10—C1	175.64 (19)
C11—C1—C2—C3	157.8 (2)	C4—C5—C10—C1	−5.7 (3)
O2—C2—C3—C4	−180.0 (2)	C2—C1—C10—C9	−166.1 (2)
C1—C2—C3—C4	3.7 (3)	C11—C1—C10—C9	26.3 (3)
O2—C2—C3—Br2	4.2 (3)	C2—C1—C10—C5	11.9 (3)
C1—C2—C3—Br2	−172.17 (16)	C11—C1—C10—C5	−155.7 (2)
C2—C3—C4—C5	2.6 (3)	C2—C1—C11—O1	40.3 (3)
Br2—C3—C4—C5	178.36 (16)	C10—C1—C11—O1	−151.6 (2)
C3—C4—C5—C6	177.2 (2)	C2—C1—C11—C12	−129.7 (2)
C3—C4—C5—C10	−1.5 (3)	C10—C1—C11—C12	38.5 (3)
C4—C5—C6—C7	179.8 (2)	O1—C11—C12—C13	−149.6 (2)
C10—C5—C6—C7	−1.6 (3)	C1—C11—C12—C13	20.5 (3)
C5—C6—C7—C8	5.3 (3)	O1—C11—C12—C17	26.3 (3)
C18—O3—C8—C9	177.92 (19)	C1—C11—C12—C17	−163.6 (2)
C18—O3—C8—C7	0.1 (3)	C17—C12—C13—C14	0.1 (3)
C6—C7—C8—O3	176.8 (2)	C11—C12—C13—C14	176.0 (2)
C6—C7—C8—C9	−1.0 (3)	C12—C13—C14—C15	1.3 (3)
O3—C8—C9—C10	174.84 (18)	C13—C14—C15—C16	−1.5 (3)
C7—C8—C9—C10	−7.2 (3)	C13—C14—C15—Cl1	178.49 (17)
O3—C8—C9—Br1	−11.4 (2)	C14—C15—C16—C17	0.2 (3)
C7—C8—C9—Br1	166.54 (16)	Cl1—C15—C16—C17	−179.73 (18)
C8—C9—C10—C5	10.7 (3)	C15—C16—C17—C12	1.2 (3)
Br1—C9—C10—C5	−162.76 (15)	C13—C12—C17—C16	−1.4 (3)
C8—C9—C10—C1	−171.3 (2)	C11—C12—C17—C16	−177.4 (2)
Br1—C9—C10—C1	15.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1	0.83	1.85	2.585 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O1	0.83	1.85	2.585 (3)	146