(8-Bromo-2-hydroxy-7-methoxy-1-naph­thyl)(4-chlorobenzoyl)methanone

Mitsui, R.; Nakaema, K.; Nagasawa, A.; Noguchi, K.; Yonezawa, N.

doi:10.1107/S1600536810006185

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o676

doi:10.1107/S1600536810006185

Open

access

(8-Bromo-2-hydroxy-7-methoxy-1-naphthyl)(4-chlorobenzoyl)methanone

Ryosuke Mitsui,^a Kosuke Nakaema,^a Atsushi Nagasawa,^a Keiichi Noguchi ^b 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, and ^bInstrumentation Analysis Center, Tokyo University of Agriculture & Technology, 2-24-16 Naka-machi, Koganei, Tokyo 184-8588, Japan
^*Correspondence e-mail: yonezawa@cc.tuat.ac.jp

(Received 9 February 2010; accepted 16 February 2010; online 20 February 2010)

In the title compound, C₁₈H₁₂BrClO₃, the naphthalene ring system and the benzene ring make a dihedral angle of 82.18 (9)°. 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. 60.91 (16)° versus 13.94 (16)°. In the crystal structure, two π–π interactions formed between the naphthalene ring systems [centroid–centroid distances of 3.8014 (13) and 3.9823 (13) Å] and intermolecular O—H⋯O and C—H⋯O hydrogen bonds are present.

Related literature

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

Experimental

Crystal data

C₁₈H₁₂BrClO₃
M_r = 391.64
Monoclinic, C 2/c
a = 23.1440 (4) Å
b = 7.61524 (14) Å
c = 20.2652 (4) Å
β = 112.733 (1)°
V = 3294.22 (10) Å³
Z = 8
Cu Kα radiation
μ = 5.00 mm⁻¹
T = 193 K
0.35 × 0.10 × 0.05 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ) T_min = 0.353, T_max = 0.779
12588 measured reflections
3004 independent reflections
2777 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.067
S = 1.30
3004 reflections
213 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.88 e Å⁻³
Δρ_min = −0.74 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O1ⁱ	0.81 (2)	1.93 (2)	2.728 (2)	172 (2)
C3—H3⋯O1ⁱ	0.95	2.58	3.205 (3)	124
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); 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 fb2182o, New_Global_Publ_Block, I. DOI: 10.1107/S1600536810006185/is2524sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810006185/is2524Isup2.hkl

checkCIF report

Comment top

Recently, we have reported the crystal structures of 1-aroylated 2,7-dimethoxynaphthalene, 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) and (4-chlorobenzoyl)(2-ethoxy-7-methoxynaphthalen-1-yl)methanone (Mitsui et al., 2009). 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 1-bromo-8-(4-chlorobenzoyl)-7-hydroxy-2-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 interplanar angle between the benzene ring (C12–C17) and the naphthalene ring (C1–C10) is 82.18 (9)°. The C═O bond vector and the least-squares plane of the benzene ring are relatively coplanar [13.94 (16)°]. By contrast, the C═O bond vector and the least-squares plane of the naphthalene ring are twisted [60.91 (15)°]. The conformation of these groups are similar to that of 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene. Intriguingly, in the compound (I), there is no intramolecular hydrogen bond in contrast with (4-chlorophenyl)(2-hydroxy-7-methoxynaphthalen-1-yl)methanone. This is presumably caused by release of the large steric repulsion brought about by the benzene ring and the bromo group in the naphthalene ring of (I).

In the crystal structure, the molecular packing of (I) is stabilized by van der Waals interactions. The 4-chlorophenyl groups interact with the carbonyl groups [H16···O1 = 2.63 Å] and the bromo groups [H16···Br1 = 3.04 Å] along the b axis, and interact with the naphthalene rings [Cl1···H4 = 2.93 Å, H17···H7 = 2.37 Å] along the a axis (Figs. 2 and 3). The carbonyl groups interact with the hydroxy groups [C11···H2O = 2.80 Å] and the naphthalene rings [O1···C3 = 3.205 (3) Å] along the b axis (Fig. 4). Additionally, the naphthalene rings of neighbouring molecules are nearly parallel, and the π systems of the C5–C10 ring (with centroid Cg) in the naphthalene group are exactly parallel. The perpendicular distance between these aromatic rings is 3.4653 (9) and 3.6483 (9) Å. The centroid–centroid distance between the parallel aromatic rings is 3.8014 (13) and 3.9823 (13) Å, and the lateral offsets are 1.563 and 1.596 Å, indicating the presence of a π–π interaction (Fig. 3). Moreover, the crystal packing is stabilized by intermolecular hydrogen bonding between the carbonyl oxygen and hydrogen atom of the hydroxy group and naphthalene ring of the adjacent molecule viz. O2—H2O···O1 and C3—H3···O1 (Fig. 4 and Table 1).

Related literature top

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

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 (161 mg, 1.01 mmol) drop-wise at 0 °C. The reaction mixture was stirred for 2 h at 0 °C, then poured into aqueous 2 M Na₂S₂O₃ (10 ml). The precipitate was collected by vacuum filtration, and washed with several times with water. The crude material was purified by recrystallization from ethanol to give the title compound as a colorless blocks (m.p. 481.5–483.0 K, yield 333 mg, 85%).

Spectroscopic Data: ¹H NMR (300 MHz, DMSO-d₆) δ 10.26 (s, 1H), 7.98 (d, 1H), 7.92 (d, 1H), 7.74 (d, 2H), 7.53 (d, 2H), 7.33 (d, 1H), 7.11 (d, 1H), 3.90 (s, 3H); ¹³C NMR (75 MHz, DMSO-d₆) δ 195.6, 155.1, 155.0, 138.3, 137.1, 131.8, 131.5, 130.2, 130.2, 128.5, 124.7, 118.4, 116.1, 110.1, 103.1, 56.7; IR (KBr): 3222, 1648, 1617, 1508, 1273, 1090; HRMS (m/z): [M + H]⁺ calcd for C₁₈H₁₃BrClO₃, 390.9737; found, 390.9705.

Anal. Calcd for C₁₈H₁₂BrClO₃: C 55.20, H 3.09. Found: C 55.04, H 2.97.

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: SHELXS97 (Sheldrick, 2008); 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.
	Fig. 2. Partial crystal packing diagram of compound (I), viewed down the c axis. van der Waals interactions are shown as dashed lines.
	Fig. 3. The arrangement of the molecules in the crystal structure, viewed in an oblique direction. van der Waals interactions and π– π interactions are shown as dashed lines.
	Fig. 4. Partial crystal packing diagram of compound (I), viewed down the b axis. van der Waals interactions and intermolecular hydrogen bonds are shown as dashed lines.

(8-Bromo-2-hydroxy-7-methoxy-1-naphthyl)(4-chlorobenzoyl)methanone top

Crystal data top

C₁₈H₁₂BrClO₃	F(000) = 1568
M_r = 391.64	D_x = 1.579 Mg m⁻³ D_m = 1.57 Mg m⁻³ D_m measured by picnomatar method
Monoclinic, C2/c	Melting point = 481.5–483.0 K
Hall symbol: -C 2yc	Cu Kα radiation, λ = 1.54187 Å
a = 23.1440 (4) Å	Cell parameters from 11710 reflections
b = 7.61524 (14) Å	θ = 3.9–68.1°
c = 20.2652 (4) Å	µ = 5.00 mm⁻¹
β = 112.733 (1)°	T = 193 K
V = 3294.22 (10) Å³	Block, colorless
Z = 8	0.35 × 0.10 × 0.05 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	3004 independent reflections
Radiation source: rotating anode	2777 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
Detector resolution: 10.00 pixels mm^-1	θ_max = 68.2°, θ_min = 4.1°
ω scans	h = −27→22
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −9→7
T_min = 0.353, T_max = 0.779	l = −24→24
12588 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 atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.067	w = 1/[σ²(F_o²) + (0.0094P)² + 5.4643P] where P = (F_o² + 2F_c²)/3
S = 1.30	(Δ/σ)_max < 0.001
3004 reflections	Δρ_max = 0.88 e Å⁻³
213 parameters	Δρ_min = −0.74 e Å⁻³
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00022 (2)

Crystal data top

C₁₈H₁₂BrClO₃	V = 3294.22 (10) Å³
M_r = 391.64	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 23.1440 (4) Å	µ = 5.00 mm⁻¹
b = 7.61524 (14) Å	T = 193 K
c = 20.2652 (4) Å	0.35 × 0.10 × 0.05 mm
β = 112.733 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3004 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	2777 reflections with I > 2σ(I)
T_min = 0.353, T_max = 0.779	R_int = 0.032
12588 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	1 restraint
wR(F²) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 1.30	Δρ_max = 0.88 e Å⁻³
3004 reflections	Δρ_min = −0.74 e Å⁻³
213 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	0.093885 (11)	0.43969 (4)	0.001360 (12)	0.03654 (11)
Cl1	−0.01318 (3)	1.17778 (10)	0.09112 (5)	0.0656 (3)
O1	0.14955 (7)	0.4263 (2)	0.17786 (8)	0.0301 (4)
O2	0.25985 (7)	0.6846 (2)	0.25441 (8)	0.0332 (4)
H2O	0.2875 (10)	0.750 (3)	0.2780 (13)	0.040*
O3	0.13753 (9)	0.3672 (3)	−0.10993 (8)	0.0441 (5)
C1	0.21864 (10)	0.5799 (3)	0.13670 (11)	0.0245 (5)
C2	0.26939 (10)	0.6442 (3)	0.19367 (11)	0.0274 (5)
C3	0.32829 (11)	0.6678 (3)	0.18978 (13)	0.0333 (5)
H3	0.3626	0.7123	0.2297	0.040*
C4	0.33562 (11)	0.6261 (3)	0.12813 (13)	0.0362 (6)
H4	0.3754	0.6421	0.1255	0.043*
C5	0.28538 (11)	0.5595 (3)	0.06792 (13)	0.0313 (5)
C6	0.29448 (13)	0.5147 (4)	0.00503 (14)	0.0388 (6)
H6	0.3348	0.5300	0.0039	0.047*
C7	0.24741 (13)	0.4504 (3)	−0.05395 (14)	0.0413 (6)
H7	0.2551	0.4197	−0.0953	0.050*
C8	0.18770 (12)	0.4300 (3)	−0.05318 (12)	0.0336 (5)
C9	0.17682 (11)	0.4728 (3)	0.00745 (12)	0.0277 (5)
C10	0.22513 (10)	0.5362 (3)	0.07094 (11)	0.0257 (5)
C11	0.15967 (10)	0.5612 (3)	0.15115 (10)	0.0241 (5)
C12	0.11712 (10)	0.7145 (3)	0.13796 (11)	0.0245 (5)
C13	0.05714 (10)	0.6943 (3)	0.13793 (12)	0.0296 (5)
H13	0.0438	0.5822	0.1471	0.036*
C14	0.01708 (11)	0.8358 (3)	0.12465 (13)	0.0358 (6)
H14	−0.0238	0.8222	0.1246	0.043*
C15	0.03738 (11)	0.9985 (3)	0.11142 (14)	0.0374 (6)
C16	0.09668 (12)	1.0226 (3)	0.11234 (14)	0.0382 (6)
H16	0.1101	1.1355	0.1042	0.046*
C17	0.13615 (11)	0.8797 (3)	0.12532 (13)	0.0319 (5)
H17	0.1770	0.8946	0.1256	0.038*
C18	0.14644 (16)	0.3312 (4)	−0.17507 (13)	0.0541 (8)
H18A	0.1071	0.2885	−0.2115	0.065*
H18B	0.1790	0.2416	−0.1660	0.065*
H18C	0.1593	0.4390	−0.1921	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03018 (15)	0.04598 (19)	0.02791 (14)	−0.00231 (11)	0.00512 (10)	−0.00651 (11)
Cl1	0.0416 (4)	0.0394 (4)	0.1165 (7)	0.0139 (3)	0.0313 (4)	0.0080 (4)
O1	0.0297 (8)	0.0266 (9)	0.0315 (8)	−0.0011 (7)	0.0090 (7)	0.0068 (7)
O2	0.0294 (9)	0.0405 (11)	0.0283 (8)	−0.0067 (7)	0.0094 (7)	−0.0108 (7)
O3	0.0567 (11)	0.0509 (12)	0.0239 (8)	−0.0086 (9)	0.0146 (8)	−0.0072 (8)
C1	0.0263 (11)	0.0210 (11)	0.0259 (10)	0.0015 (9)	0.0097 (9)	0.0016 (9)
C2	0.0283 (11)	0.0240 (12)	0.0300 (11)	0.0010 (9)	0.0113 (9)	−0.0020 (9)
C3	0.0281 (12)	0.0324 (13)	0.0367 (12)	−0.0027 (10)	0.0096 (10)	−0.0058 (11)
C4	0.0294 (12)	0.0360 (14)	0.0475 (14)	−0.0031 (11)	0.0196 (11)	−0.0036 (12)
C5	0.0351 (13)	0.0263 (13)	0.0370 (13)	−0.0013 (10)	0.0187 (10)	−0.0008 (10)
C6	0.0443 (14)	0.0386 (15)	0.0445 (14)	−0.0044 (12)	0.0291 (12)	−0.0027 (12)
C7	0.0609 (17)	0.0378 (15)	0.0360 (13)	−0.0052 (13)	0.0303 (13)	−0.0030 (11)
C8	0.0474 (15)	0.0271 (13)	0.0270 (11)	−0.0038 (11)	0.0153 (10)	−0.0006 (10)
C9	0.0326 (12)	0.0237 (12)	0.0271 (11)	0.0002 (10)	0.0117 (9)	0.0028 (9)
C10	0.0306 (11)	0.0199 (11)	0.0271 (11)	0.0001 (9)	0.0118 (9)	0.0020 (9)
C11	0.0259 (11)	0.0255 (12)	0.0171 (9)	−0.0026 (9)	0.0040 (8)	−0.0026 (8)
C12	0.0266 (11)	0.0256 (12)	0.0209 (10)	−0.0006 (9)	0.0088 (8)	−0.0003 (9)
C13	0.0281 (11)	0.0289 (13)	0.0312 (11)	−0.0046 (10)	0.0108 (9)	−0.0002 (10)
C14	0.0252 (12)	0.0376 (15)	0.0439 (14)	−0.0024 (11)	0.0126 (10)	−0.0035 (11)
C15	0.0301 (12)	0.0312 (14)	0.0483 (14)	0.0049 (11)	0.0121 (11)	−0.0020 (11)
C16	0.0357 (13)	0.0256 (13)	0.0533 (15)	−0.0002 (11)	0.0172 (12)	0.0037 (11)
C17	0.0282 (12)	0.0302 (13)	0.0399 (13)	−0.0004 (10)	0.0160 (10)	0.0036 (10)
C18	0.087 (2)	0.0512 (19)	0.0263 (13)	−0.0088 (17)	0.0243 (14)	−0.0067 (12)

Geometric parameters (Å, º) top

Br1—C9	1.892 (2)	C7—C8	1.397 (4)
Cl1—C15	1.741 (3)	C7—H7	0.9500
O1—C11	1.225 (3)	C8—C9	1.385 (3)
O2—C2	1.367 (3)	C9—C10	1.424 (3)
O2—H2O	0.808 (17)	C11—C12	1.484 (3)
O3—C8	1.366 (3)	C12—C17	1.389 (3)
O3—C18	1.439 (3)	C12—C13	1.396 (3)
C1—C2	1.380 (3)	C13—C14	1.379 (3)
C1—C10	1.437 (3)	C13—H13	0.9500
C1—C11	1.509 (3)	C14—C15	1.387 (4)
C2—C3	1.407 (3)	C14—H14	0.9500
C3—C4	1.362 (3)	C15—C16	1.378 (3)
C3—H3	0.9500	C16—C17	1.379 (3)
C4—C5	1.415 (3)	C16—H16	0.9500
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.411 (3)	C18—H18A	0.9800
C5—C10	1.430 (3)	C18—H18B	0.9800
C6—C7	1.360 (4)	C18—H18C	0.9800
C6—H6	0.9500

C2—O2—H2O	108 (2)	C9—C10—C1	126.1 (2)
C8—O3—C18	117.5 (2)	C5—C10—C1	117.7 (2)
C2—C1—C10	119.9 (2)	O1—C11—C12	120.8 (2)
C2—C1—C11	114.35 (19)	O1—C11—C1	120.4 (2)
C10—C1—C11	125.79 (19)	C12—C11—C1	118.53 (19)
O2—C2—C1	116.9 (2)	C17—C12—C13	119.0 (2)
O2—C2—C3	121.3 (2)	C17—C12—C11	120.7 (2)
C1—C2—C3	121.9 (2)	C13—C12—C11	120.3 (2)
C4—C3—C2	119.2 (2)	C14—C13—C12	120.5 (2)
C4—C3—H3	120.4	C14—C13—H13	119.7
C2—C3—H3	120.4	C12—C13—H13	119.7
C3—C4—C5	121.5 (2)	C13—C14—C15	118.9 (2)
C3—C4—H4	119.2	C13—C14—H14	120.6
C5—C4—H4	119.2	C15—C14—H14	120.6
C6—C5—C4	120.4 (2)	C16—C15—C14	121.8 (2)
C6—C5—C10	119.8 (2)	C16—C15—Cl1	118.3 (2)
C4—C5—C10	119.8 (2)	C14—C15—Cl1	119.93 (19)
C7—C6—C5	122.2 (2)	C15—C16—C17	118.7 (2)
C7—C6—H6	118.9	C15—C16—H16	120.7
C5—C6—H6	118.9	C17—C16—H16	120.7
C6—C7—C8	119.4 (2)	C16—C17—C12	121.1 (2)
C6—C7—H7	120.3	C16—C17—H17	119.5
C8—C7—H7	120.3	C12—C17—H17	119.5
O3—C8—C9	116.2 (2)	O3—C18—H18A	109.5
O3—C8—C7	123.5 (2)	O3—C18—H18B	109.5
C9—C8—C7	120.2 (2)	H18A—C18—H18B	109.5
C8—C9—C10	122.2 (2)	O3—C18—H18C	109.5
C8—C9—Br1	116.00 (17)	H18A—C18—H18C	109.5
C10—C9—Br1	121.80 (17)	H18B—C18—H18C	109.5
C9—C10—C5	116.2 (2)

C10—C1—C2—O2	179.4 (2)	C4—C5—C10—C9	178.4 (2)
C11—C1—C2—O2	−1.0 (3)	C6—C5—C10—C1	178.6 (2)
C10—C1—C2—C3	−0.5 (3)	C4—C5—C10—C1	−1.0 (3)
C11—C1—C2—C3	179.2 (2)	C2—C1—C10—C9	−178.4 (2)
O2—C2—C3—C4	−179.9 (2)	C11—C1—C10—C9	2.0 (4)
C1—C2—C3—C4	0.0 (4)	C2—C1—C10—C5	1.0 (3)
C2—C3—C4—C5	−0.1 (4)	C11—C1—C10—C5	−178.6 (2)
C3—C4—C5—C6	−179.0 (2)	C2—C1—C11—O1	−87.5 (3)
C3—C4—C5—C10	0.6 (4)	C10—C1—C11—O1	92.1 (3)
C4—C5—C6—C7	−180.0 (3)	C2—C1—C11—C12	87.5 (2)
C10—C5—C6—C7	0.4 (4)	C10—C1—C11—C12	−92.9 (3)
C5—C6—C7—C8	1.0 (4)	O1—C11—C12—C17	163.4 (2)
C18—O3—C8—C9	176.5 (2)	C1—C11—C12—C17	−11.6 (3)
C18—O3—C8—C7	−4.0 (4)	O1—C11—C12—C13	−16.8 (3)
C6—C7—C8—O3	179.7 (2)	C1—C11—C12—C13	168.26 (19)
C6—C7—C8—C9	−0.8 (4)	C17—C12—C13—C14	0.8 (3)
O3—C8—C9—C10	178.7 (2)	C11—C12—C13—C14	−179.0 (2)
C7—C8—C9—C10	−0.9 (4)	C12—C13—C14—C15	−0.1 (4)
O3—C8—C9—Br1	−0.6 (3)	C13—C14—C15—C16	−1.1 (4)
C7—C8—C9—Br1	179.81 (19)	C13—C14—C15—Cl1	177.56 (19)
C8—C9—C10—C5	2.2 (3)	C14—C15—C16—C17	1.4 (4)
Br1—C9—C10—C5	−178.52 (16)	Cl1—C15—C16—C17	−177.2 (2)
C8—C9—C10—C1	−178.4 (2)	C15—C16—C17—C12	−0.6 (4)
Br1—C9—C10—C1	0.9 (3)	C13—C12—C17—C16	−0.5 (3)
C6—C5—C10—C9	−2.0 (3)	C11—C12—C17—C16	179.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1ⁱ	0.81 (2)	1.93 (2)	2.728 (2)	172 (2)
C3—H3···O1ⁱ	0.95	2.58	3.205 (3)	124

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₂BrClO₃
M_r	391.64
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	193
a, b, c (Å)	23.1440 (4), 7.61524 (14), 20.2652 (4)
β (°)	112.733 (1)
V (Å³)	3294.22 (10)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	5.00
Crystal size (mm)	0.35 × 0.10 × 0.05

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.353, 0.779
No. of measured, independent and observed [I > 2σ(I)] reflections	12588, 3004, 2777
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.067, 1.30
No. of reflections	3004
No. of parameters	213
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.88, −0.74

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), 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···O1ⁱ	0.81 (2)	1.93 (2)	2.728 (2)	172 (2)
C3—H3···O1ⁱ	0.95	2.58	3.205 (3)	124

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

This work was partially supported by the Ogasawara Foundation for the Promotion of Science & Engineering, Tokyo, Japan.

References

Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory. Tennessee, USA. Google Scholar
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan. Google Scholar
Mitsui, R., Nakaema, K., Noguchi, K., Okamoto, A. & Yonezawa, N. (2008). Acta Cryst. E64, o1278. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mitsui, R., Nakaema, K., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o2497. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mitsui, R., Noguchi, K. & Yonezawa, N. (2009). Acta Cryst. E65, o543. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar