(8-Bromo-2,7-dimeth­oxy-1-naphth­yl)(4-chloro­phenyl)methanone

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

doi:10.1107/S1600536810009463

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o873

doi:10.1107/S1600536810009463

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(8-Bromo-2,7-dimethoxy-1-naphthyl)(4-chlorophenyl)methanone

Ryosuke Mitsui,^a Atsushi Nagasawa,^a Shoji Watanabe,^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 10 March 2010; accepted 12 March 2010; online 20 March 2010)

In the title compound, C₁₉H₁₄BrClO₃, 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 interaction is formed between naphthalene ring systems, with a centroid–centroid distance of 3.8363 (14) Å and a lateral offset of 1.606 Å. Intermolecular 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_r = 405.66
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.086
S = 1.07
3092 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.43 e Å⁻³

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⋯Cg1^iv	0.98	2.70	3.509 (3)	140
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x, -y, -z+1; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) -x, -y+1, -z+1.

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: 10.1107/S1600536810009463/is2530sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810009463/is2530Isup2.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) and 1-bromo-8-(4-chlorobenzoyl)-7-hydroxy-2-methoxynaphthalene (Mitsui 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 1-bromo-8-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene, (I). The title compound was prepared by methylation of 1-bromo-8-(4-chlorobenzoyl)-7-hydroxy-2-methoxynaphthalene with dimethyl sulfonate.

An ORTEPIII (Burnett & Johnson, 1996) plot of (I) is shown in Fig. 1. In the molecule of (I), the dihedral angle between the benzene ring (C12–C17) and the naphthalene ring (C1–C10) is 77.36 (10)°. The C═O bond vector and the least-squares plane of the benzene ring are almost coplanar [2.33 (17)°]. By contrast, the C═O bond vector and the least-squares plane of the naphthalene ring are largely twisted [75.73 (15)°]. The conformation of these groups resembles to that of 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene.

In the crystal structure, all H atoms belonging the methoxy group in the 7-position of naphthalene ring, interact with adjacent molecule constructing intermolecular C—H···Br, C—H···O hydrogen bonds and C—H···π contact, respectively (Table 1). H19A and Br1 interact with each other [H19A···Br1 = 2.92 Å] along the b axis (Fig. 2). H19C interacts with the carbonyl oxygen [H19C···O1 = 2.53 Å] along the b axis (Fig. 3). The carbonyl oxygen also interacts with naphthalene ring hydrogen [O1···H4 = 2.49 Å] along the c axis (Figs. 2 and 3). The methoxy group acts as a hydrogen-bond donor and the π system of the naphthalene ring [C1/C2/C3/C4/C5/C10 ring (with centroid Cg1)] of an adjacent molecule acts as an acceptor, viz. C19—H19B···π (Fig. 4 and Table 1). Additionally, the π systems of the C5–C10 ring (with centroid Cg2) in the naphthalene group are exactly parallel. The perpendicular distance between these aromatic rings is 3.4840 (10) Å. The centroid–centroid distance between the parallel aromatic rings is 3.8363 (14) Å, and the lateral offsets are 1.606 Å, indicating the presence of a π–π interaction (Fig. 4).

Related literature top

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 top

1-Bromo-8-(4-chlorobenzoyl)-7-hydroxy-2-methoxynaphthalene (1.56 g, 4.0 mmol) was dissolved in acetone (5.0 ml) and aqueous 0.4 M NaOH (5.0 ml). Then, dimethyl sulfate (0.78 ml, 8.0 mmol) was added and the reaction mixture was stirred for 6 h at room temperature. The mixture was concentrated by evaporation and poured into a mixture of H₂O (10 ml) and CHCl₃ (10 ml), and the aqueous layer was extracted with CHCl₃ (3 × 10 ml). The combined organic layers were washed with brine (3 × 30 ml), and dried over MgSO₄ overnight. The solvent was removed in vacuo and the crude material was purified by recrystallization from CHCl₃/hexane to give the title compound as colorless platelets (m.p. 447.0–447.5 K, yield 1.43 g, 88%).

Spectroscopic Data: ¹H NMR (300 MHz, CDCl₃) δ 7.88–7.79 (m, 4H), 7.37 (d, 2H), 7.21–7.15 (m, 2H), 3.95 (s, 3H), 3.75 (s, 3H); ¹³C NMR (75 MHz, CDCl₃) δ 196.5, 157.2, 155.7, 138.7, 138.6, 132.2, 131.9, 130.4, 130.1, 128.7, 126.3, 122.5, 111.8, 111.6, 104.9, 57.0, 56.8; IR (KBr): 1665, 1613, 1506, 1273, 1043, 827; HRMS (m/z): [M + H]⁺ calcd for C₁₉H₁₅BrClO₃, 404.9893 found, 404.9862. Anal. Calcd for C₁₉H₁₄BrClO₃: C 56.25, H 3.48. Found: C 56.48, H 3.42.

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.
	Fig. 2. Partial packing diagram of compound (I), viewed down the a axis. Intermolecular C—H···Br and C—H···O hydrogen bonds are shown as dashed lines.
	Fig. 3. Partial packing diagram of compound (I), viewed down the a axis. Intermolecular C—H···O hydrogen bonds are shown as dashed lines.
	Fig. 4. The arrangement of the molecules, viewed in an oblique direction. Intermolecular C—H···π and π–π interactions are shown as dashed lines.

(8-Bromo-2,7-dimethoxy-1-naphthyl)(4-chlorophenyl)methanone top

Crystal data top

C₁₉H₁₄BrClO₃	F(000) = 816
M_r = 405.66	D_x = 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

Data collection top

Rigaku R-AXIS RAPID diffractometer	3092 independent reflections
Radiation source: rotating anode	2845 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
Detector resolution: 10.00 pixels mm^-1	θ_max = 68.2°, θ_min = 3.1°
ω scans	h = −18→18
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −10→10
T_min = 0.160, T_max = 0.614	l = −16→15
26838 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)] = 0.034	H-atom parameters constrained
wR(F²) = 0.086	w = 1/[σ²(F_o²) + (0.036P)² + 0.9139P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
3092 reflections	Δρ_max = 0.45 e Å⁻³
220 parameters	Δρ_min = −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)

Crystal data top

C₁₉H₁₄BrClO₃	V = 1695.64 (6) Å³
M_r = 405.66	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 15.0867 (3) Å	µ = 4.88 mm⁻¹
b = 8.72313 (16) Å	T = 193 K
c = 13.5894 (3) Å	0.50 × 0.40 × 0.20 mm
β = 108.536 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3092 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	2845 reflections with I > 2σ(I)
T_min = 0.160, T_max = 0.614	R_int = 0.071
26838 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.07	Δρ_max = 0.45 e Å⁻³
3092 reflections	Δρ_min = −0.43 e Å⁻³
220 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	0.147755 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···Cg1^iv	0.98	2.70	3.509 (3)	140

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x, −y, −z+1; (iii) x, −y+1/2, z+1/2; (iv) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₄BrClO₃
M_r	405.66
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	15.0867 (3), 8.72313 (16), 13.5894 (3)
β (°)	108.536 (1)
V (Å³)	1695.64 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	4.88
Crystal size (mm)	0.50 × 0.40 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.160, 0.614
No. of measured, independent and observed [I > 2σ(I)] reflections	26838, 3092, 2845
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.086, 1.07
No. of reflections	3092
No. of parameters	220
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.43

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

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···Cg1^iv	0.98	2.70	3.509 (3)	140

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) −x, −y, −z+1; (iii) x, −y+1/2, z+1/2; (iv) −x, −y+1, −z+1.

Acknowledgements

The authors would 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

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 66| Part 4| April 2010| Page o873

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