(8-Bromo-2-hydroxy-7-methoxy-1-naph-thyl)(4-chlorobenzoyl)methanone.

In the title compound, C(18)H(12)BrClO(3), 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 inter-actions formed between the naphthalene ring systems [centroid-centroid distances of 3.8014 (13) and 3.9823 (13) Å] and inter-molecular 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 = 391.64

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.067

S = 1.30

3004 reflections

213 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.88 e Å−3

Δρmin = −0.74 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: 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.

Crystal structure: contains datablocks fb2182o, New_Global_Publ_Block, I. DOI: 10.1107/S1600536810006185/is2524sup1.cif

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

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

C18H12BrClO3	F(000) = 1568
Mr = 391.64	Dx = 1.579 Mg m−3Dm = 1.57 Mg m−3Dm 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

Rigaku R-AXIS RAPID diffractometer	3004 independent reflections
Radiation source: rotating anode	2777 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 10.00 pixels mm-1	θmax = 68.2°, θmin = 4.1°
ω scans	h = −27→22
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −9→7
Tmin = 0.353, Tmax = 0.779	l = −24→24
12588 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 atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.067	w = 1/[σ2(Fo2) + (0.0094P)2 + 5.4643P] where P = (Fo2 + 2Fc2)/3
S = 1.30	(Δ/σ)max < 0.001
3004 reflections	Δρmax = 0.88 e Å−3
213 parameters	Δρmin = −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)

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	0.093885 (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*

	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)

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)

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

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) .