(4-Chloro­phen­yl)(3,8-dibromo-2-hydr­oxy-7-meth­oxy-1-naphth­yl)methanone

Mitsui, R.; Watanabe, S.; Nagasawa, A.; Okamoto, A.; Yonezawa, N.

doi:10.1107/S1600536810015527

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1304

https://doi.org/10.1107/S1600536810015527

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(4-Chlorophenyl)(3,8-dibromo-2-hydroxy-7-methoxy-1-naphthyl)methanone

Ryosuke Mitsui,^a Shoji Watanabe,^a Atsushi Nagasawa,^a Akiko Okamoto ^a and Noriyuki Yonezawa ^a ^*

^aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-machi, Koganei, Tokyo 184-8588, Japan
^*Correspondence e-mail: yonezawa@cc.tuat.ac.jp

(Received 22 April 2010; accepted 27 April 2010; online 8 May 2010)

In the title compound, C₁₈H₁₁Br₂ClO₃, an intramolecular 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 intermolecular 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_r = 470.54
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.028
wR(F²) = 0.076
S = 1.11
3022 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.64 e Å⁻³

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

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810015527/is2542sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015527/is2542Isup2.hkl

checkCIF report

Comment top

Recently, we reported the crystal structures of 1-aroylated 2,7-dimethoxynaphthalenes, 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Mitsui, Nakaema, Noguchi, Okamoto & Yonezawa, 2008), (4-chlorophenyl)(2-hydroxy-7-methoxynaphthalen-1-yl)methanone (Mitsui, Nakaema, Noguchi & Yonezawa, 2008), (4-chlorophenyl)(2-ethoxy-7-methoxynaphthalen-1-yl)methanone (Mitsui et al., 2009), 1-bromo-8-(4-chlorobenzoyl)-7-hydroxy-2-methoxynaphthalene (Mitsui, Nakaema, Nagasawa et al., 2010) and (8-bromo-2,7-dimethoxy-1-naphthyl)(4-chlorophenyl)methanone (Mitsui, Nagasawa, Watanabe et al., 2010). As a part of our ongoing studies on the synthesis and crystal structure analysis of aroylated naphthalene derivatives, we prepared and analysed the structure of crystal of 2,5-dibromo-4-(4-chlorobenzoyl)-3-hydroxy-6-methoxynaphthalene, (I). The title compound was prepared by electrophilic aromatic bromination reaction of (4-chlorophenyl)(2-hydroxy-7-methoxynaphthalen-1-yl)methanone with bromine.

An ORTEPIII (Burnett & Johnson, 1996) plot of (I) is shown in Fig. 1. In the molecule of (I), the intramolecular O—H···O═C hydrogen bond, which forms a six-membered ring including the C═O group and an edge of the naphthalene ring, is present (Table 1). The conformation of these groups resembles to that of (4-chlorophenyl)(2-hydroxy-7-methoxynaphthalen-1-yl)methanone (Mitsui, Nakaema, Noguchi & Yonezawa, 2008). Intriguingly, the central C═O group is twisted away from the naphthalene ring and the benzene ring, and the bromo group at 8-position of naphthalene is out of the least-squares plane of the naphthalene ring. The angles of the C═O bond vector against the least-squares plane of the naphthalene ring and the benzene ring are 18.61 (15) and 26.25 (16)°, respectively. The angle of the C9—Br1 bond vector against the least-squares plane of the naphthalene ring is 14.93 (7)°. This is presumably caused by release of the large steric repulsion brought about by the benzene ring and the bromo group on the naphthalene ring of (I).

In the crystal structure, the contact distances Br1···Cl1 and Br2···Cl1 are 3.4927 (7) and 3.4325 (7) Å, respectively (Fig. 2). These contacts are shorter than the sum of their van der Waals radii (3.60 Å), and the five atoms are arranged nearly linear [C9—Br1···Cl1 = 154.14 (6)°, C3—Br2···Cl1 = 165.35 (7)°], suggesting that there is a possibility for halogen interaction (Saruma & Desiraju, 1986; Pedireddi et al., 1994; Moorthy et al., 2002).

Related literature top

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 top

To a solution of (4-chlorophenyl)(2-hydroxy-7-methoxynaphthalen-1-yl)methanone (313 mg, 1.00 mmol) in chloroform (5 ml) was added Br₂ (483 mg, 3.03 mmol) drop-wise. The reaction mixture was heated at reflux for 2 h, then poured into aqueous 2 M Na₂S₂O₃ (10 ml), and the aqueous layer was extracted with CHCl₃ (3 × 10 ml). The combined organic layers were washed with 2 M Na₂S₂O₃ (3 × 30 ml) and brine (3 × 30 ml), and dried over MgSO₄ overnight. The solvent was removed in vacuo and the crude material was purified by column chromatography (silica gel, CHCl₃) to give the title compound (yield 306 mg, 65%). Single crystals suitable for X-ray diffraction analysis were obtained from CHCl₃ as yellow blocks (m.p. 455.0–455.5 K).

Spectroscopic Data: ¹H NMR (300 MHz, CDCl₃) δ 8.10 (s, 1H), 8.04 (s, 1H), 7.75 (d, 1H), 7.58 (d, 2H), 7.31 (d, 2H), 7.17 (d, 1H), 3.95 (s, 3H); ¹³C NMR (75 MHz, CDCl₃) δ 195.6, 156.3, 152.6, 139.3, 138.3, 134.9, 132.4, 130.3, 129.1, 128.8, 125.8, 118.1, 112.2, 110.5, 105.9, 56.9; IR (KBr): 1670, 1607, 1587, 1495, 1276, 1215, 1096, 782; HRMS (m/z): [M + H]⁺ calcd for C₁₈H₁₂Br₂ClO₃, 468.8842 found, 468.8839. Anal. Calcd for C₁₈H₁₁Br₂ClO₃: C 45.95, H 2.36. Found: C 46.23, H 2.39.

Structure description top

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).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of compound (I), showing 50% probability displacement ellipsoids. The intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. Partial crystal packing diagram of compound (I), viewed down the b axis. Halogen-halogen interactions are shown as dashed lines.

(4-Chlorophenyl)(3,8-dibromo-2-hydroxy-7-methoxy-1-naphthyl)methanone top

Crystal data top

C₁₈H₁₁Br₂ClO₃	F(000) = 920
M_r = 470.54	D_x = 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

Data collection top

Rigaku R-AXIS RAPID diffractometer	3022 independent reflections
Radiation source: rotating anode	2940 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
Detector resolution: 10.00 pixels mm^-1	θ_max = 68.3°, θ_min = 3.7°
ω scans	h = −14→14
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −12→12
T_min = 0.189, T_max = 0.308	l = −16→16
29373 measured reflections

Refinement top

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(F_o²) + (0.0457P)² + 0.9314P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max = 0.001
3022 reflections	Δρ_max = 0.60 e Å⁻³
219 parameters	Δρ_min = −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)

Crystal data top

C₁₈H₁₁Br₂ClO₃	V = 1650.79 (5) Å³
M_r = 470.54	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 12.1513 (2) Å	µ = 7.85 mm⁻¹
b = 10.06343 (18) Å	T = 193 K
c = 13.8936 (3) Å	0.30 × 0.25 × 0.20 mm
β = 103.675 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3022 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	2940 reflections with I > 2σ(I)
T_min = 0.189, T_max = 0.308	R_int = 0.068
29373 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 1.11	Δρ_max = 0.60 e Å⁻³
3022 reflections	Δρ_min = −0.64 e Å⁻³
219 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₁Br₂ClO₃
M_r	470.54
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	12.1513 (2), 10.06343 (18), 13.8936 (3)
β (°)	103.675 (1)
V (Å³)	1650.79 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	7.85
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.189, 0.308
No. of measured, independent and observed [I > 2σ(I)] reflections	29373, 3022, 2940
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.076, 1.11
No. of reflections	3022
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.64

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top

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

Acknowledgements

The authors would like to express their gratitude to Professor Keiichi Noguchi for technical advice. This work was partially supported by the Ogasawara Foundation for the Promotion of Science & Engineering, Tokyo, Japan.

References

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