(4-Chlorophenyl)(2-hydroxy-7-methoxynaphthalen-1-yl)methanone.

The title compound, C(18)H(13)ClO(3), has an intra-molecular O-H⋯O=C hydrogen bond between the carbonyl group and the hydr-oxy substituent on the naphthalene ring system. The angle between the C=O bond plane and the naphthalene ring system is relatively small [20.96 (8)°]. The angle between the benzene ring and the carbonyl group is rather large [35.65 (9)°] compared to that in an analogous compound [3.43 (11)°] having a meth-oxy group instead of a hydroxy substituent.

Related literature

For the structures of closely related compounds, see: Nakaema et al. (2007 ▶, 2008 ▶); Mitsui et al. (2008 ▶).

Experimental

Crystal data

C18H13ClO3

M = 312.73

Orthorhombic,

a = 17.8030 (3) Å

b = 8.68121 (10) Å

c = 18.8683 (3) Å

V = 2916.14 (8) Å3

Z = 8

Cu Kα radiation

μ = 2.41 mm−1

T = 123 K

0.60 × 0.15 × 0.05 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.485, T max = 0.886

49864 measured reflections

2669 independent reflections

2347 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.096

S = 1.08

2669 reflections

205 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.25 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 global, I. DOI: 10.1107/S1600536808039603/su2069sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039603/su2069Isup2.hkl

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

C18H13ClO3	Dx = 1.425 Mg m−3
Mr = 312.73	Melting point = 391.0–391.5 K
Orthorhombic, Pbca	Cu Kα radiation λ = 1.54187 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 42602 reflections
a = 17.8030 (3) Å	θ = 3.4–68.2º
b = 8.68121 (10) Å	µ = 2.41 mm−1
c = 18.8683 (3) Å	T = 123 K
V = 2916.14 (8) Å3	Plate, yellow
Z = 8	0.60 × 0.15 × 0.05 mm
F000 = 1296

Rigaku R-AXIS RAPID diffractometer	2669 independent reflections
Radiation source: rotating anode	2347 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
Detector resolution: 10.00 pixels mm-1	θmax = 68.2º
T = 123 K	θmin = 4.7º
ω scans	h = −21→21
Absorption correction: numerical(NUMABS; Higashi, 1999)	k = −10→10
Tmin = 0.485, Tmax = 0.886	l = −22→22
49864 measured reflections

Refinement on F2	Hydrogen site location: dfimap
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.033	w = 1/[σ2(Fo2) + (0.0544P)2 + 0.6658P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096	(Δ/σ)max = 0.001
S = 1.08	Δρmax = 0.17 e Å−3
2669 reflections	Δρmin = −0.25 e Å−3
205 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00062 (11)
Secondary atom site location: difference Fourier map

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
Cl1	−0.05110 (2)	0.23154 (6)	0.500766 (19)	0.05295 (17)
O1	0.04658 (5)	0.08073 (14)	0.17181 (6)	0.0439 (3)
O2	0.12423 (7)	0.21814 (15)	0.07692 (6)	0.0485 (3)
H2	0.0840 (13)	0.163 (3)	0.0974 (11)	0.070 (7)*
O3	0.29872 (6)	0.03670 (13)	0.41875 (6)	0.0474 (3)
C1	0.16824 (8)	0.17285 (16)	0.19660 (7)	0.0299 (3)
C2	0.17846 (9)	0.22425 (17)	0.12659 (8)	0.0373 (3)
C3	0.24694 (10)	0.28979 (18)	0.10428 (8)	0.0432 (4)
H3	0.2518	0.3289	0.0575	0.052*
C4	0.30589 (9)	0.29694 (18)	0.14974 (9)	0.0415 (4)
H4	0.3514	0.3439	0.1347	0.050*
C5	0.36473 (8)	0.23357 (18)	0.26380 (10)	0.0419 (4)
H5	0.4104	0.2779	0.2476	0.050*
C6	0.36219 (8)	0.16956 (18)	0.32922 (9)	0.0433 (4)
H6	0.4052	0.1714	0.3590	0.052*
C7	0.29510 (8)	0.10024 (17)	0.35260 (8)	0.0368 (3)
C8	0.23210 (7)	0.09796 (16)	0.31021 (7)	0.0312 (3)
H8	0.1880	0.0473	0.3262	0.037*
C9	0.23251 (7)	0.17038 (15)	0.24311 (7)	0.0293 (3)
C10	0.30113 (7)	0.23607 (16)	0.21894 (9)	0.0341 (3)
C11	0.09175 (7)	0.12732 (16)	0.21759 (8)	0.0325 (3)
C12	0.06218 (7)	0.14707 (16)	0.29105 (8)	0.0304 (3)
C13	0.00695 (8)	0.04620 (17)	0.31572 (8)	0.0354 (3)
H13	−0.0079	−0.0389	0.2873	0.042*
C14	−0.02637 (8)	0.06910 (18)	0.38113 (8)	0.0389 (4)
H14	−0.0630	−0.0011	0.3984	0.047*
C15	−0.00543 (8)	0.19623 (18)	0.42098 (8)	0.0364 (3)
C16	0.04883 (8)	0.29823 (17)	0.39772 (8)	0.0346 (3)
H16	0.0626	0.3846	0.4258	0.041*
C17	0.08296 (8)	0.27253 (16)	0.33264 (8)	0.0320 (3)
H17	0.1208	0.3411	0.3163	0.038*
C18	0.23232 (12)	−0.0353 (2)	0.44536 (9)	0.0560 (5)
H18A	0.2422	−0.0770	0.4927	0.067*
H18B	0.2174	−0.1192	0.4135	0.067*
H18C	0.1918	0.0407	0.4481	0.067*

	U11	U22	U33	U12	U13	U23
Cl1	0.0399 (3)	0.0813 (4)	0.0376 (2)	−0.0016 (2)	0.00670 (15)	0.00181 (19)
O1	0.0292 (6)	0.0561 (7)	0.0463 (6)	−0.0002 (5)	−0.0077 (4)	−0.0137 (5)
O2	0.0513 (7)	0.0577 (8)	0.0364 (6)	0.0083 (6)	−0.0084 (5)	−0.0005 (5)
O3	0.0542 (7)	0.0414 (6)	0.0466 (6)	0.0105 (5)	−0.0200 (5)	−0.0052 (5)
C1	0.0286 (7)	0.0260 (7)	0.0351 (7)	0.0025 (5)	−0.0004 (5)	−0.0043 (5)
C2	0.0416 (8)	0.0317 (8)	0.0385 (8)	0.0069 (6)	−0.0016 (6)	−0.0048 (6)
C3	0.0554 (9)	0.0328 (9)	0.0413 (8)	0.0008 (7)	0.0116 (8)	0.0006 (7)
C4	0.0395 (8)	0.0313 (8)	0.0536 (10)	−0.0038 (6)	0.0153 (7)	−0.0075 (7)
C5	0.0245 (7)	0.0363 (8)	0.0649 (10)	−0.0006 (6)	0.0027 (7)	−0.0195 (7)
C6	0.0268 (7)	0.0396 (9)	0.0635 (11)	0.0073 (6)	−0.0130 (7)	−0.0200 (8)
C7	0.0368 (8)	0.0295 (8)	0.0441 (8)	0.0104 (6)	−0.0112 (6)	−0.0111 (6)
C8	0.0274 (7)	0.0263 (7)	0.0398 (7)	0.0028 (5)	−0.0033 (5)	−0.0053 (6)
C9	0.0253 (7)	0.0237 (7)	0.0388 (7)	0.0025 (5)	0.0001 (5)	−0.0074 (5)
C10	0.0276 (7)	0.0267 (7)	0.0482 (9)	0.0006 (5)	0.0051 (6)	−0.0102 (6)
C11	0.0264 (7)	0.0290 (7)	0.0422 (8)	0.0029 (6)	−0.0056 (6)	−0.0043 (6)
C12	0.0213 (6)	0.0298 (7)	0.0402 (7)	0.0025 (5)	−0.0033 (5)	−0.0007 (6)
C13	0.0263 (7)	0.0305 (8)	0.0493 (8)	0.0003 (6)	−0.0043 (6)	−0.0018 (6)
C14	0.0274 (7)	0.0392 (9)	0.0502 (9)	−0.0027 (6)	−0.0010 (6)	0.0097 (7)
C15	0.0281 (7)	0.0448 (9)	0.0363 (7)	0.0057 (6)	0.0007 (6)	0.0059 (6)
C16	0.0312 (7)	0.0342 (8)	0.0383 (8)	0.0026 (6)	−0.0017 (6)	−0.0028 (6)
C17	0.0258 (7)	0.0298 (7)	0.0405 (8)	0.0001 (5)	−0.0008 (6)	0.0000 (6)
C18	0.0896 (14)	0.0381 (9)	0.0402 (9)	−0.0063 (9)	−0.0156 (9)	0.0008 (7)

Cl1—C15	1.7381 (15)	C7—C8	1.3778 (19)
O1—C11	1.2476 (17)	C8—C9	1.414 (2)
O2—C2	1.3466 (19)	C8—H8	0.9500
O2—H2	0.94 (2)	C9—C10	1.4233 (19)
O3—C7	1.3661 (19)	C11—C12	1.493 (2)
O3—C18	1.429 (2)	C12—C17	1.392 (2)
C1—C2	1.406 (2)	C12—C13	1.397 (2)
C1—C9	1.4422 (19)	C13—C14	1.384 (2)
C1—C11	1.4722 (19)	C13—H13	0.9500
C2—C3	1.410 (2)	C14—C15	1.387 (2)
C3—C4	1.357 (2)	C14—H14	0.9500
C3—H3	0.9500	C15—C16	1.382 (2)
C4—C10	1.411 (2)	C16—C17	1.388 (2)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.354 (3)	C17—H17	0.9500
C5—C10	1.414 (2)	C18—H18A	0.9800
C5—H5	0.9500	C18—H18B	0.9800
C6—C7	1.408 (2)	C18—H18C	0.9800
C6—H6	0.9500
C2—O2—H2	106.3 (13)	C4—C10—C9	119.88 (14)
C7—O3—C18	117.31 (12)	C5—C10—C9	119.30 (15)
C2—C1—C9	118.28 (13)	O1—C11—C1	119.80 (13)
C2—C1—C11	117.23 (13)	O1—C11—C12	116.93 (12)
C9—C1—C11	124.48 (12)	C1—C11—C12	123.04 (12)
O2—C2—C1	123.27 (15)	C17—C12—C13	119.32 (13)
O2—C2—C3	115.35 (14)	C17—C12—C11	121.30 (13)
C1—C2—C3	121.36 (14)	C13—C12—C11	119.07 (13)
C4—C3—C2	119.91 (15)	C14—C13—C12	120.60 (14)
C4—C3—H3	120.0	C14—C13—H13	119.7
C2—C3—H3	120.0	C12—C13—H13	119.7
C3—C4—C10	121.42 (14)	C13—C14—C15	118.87 (14)
C3—C4—H4	119.3	C13—C14—H14	120.6
C10—C4—H4	119.3	C15—C14—H14	120.6
C6—C5—C10	121.68 (15)	C16—C15—C14	121.71 (14)
C6—C5—H5	119.2	C16—C15—Cl1	119.28 (12)
C10—C5—H5	119.2	C14—C15—Cl1	118.97 (12)
C5—C6—C7	119.28 (14)	C15—C16—C17	118.95 (14)
C5—C6—H6	120.4	C15—C16—H16	120.5
C7—C6—H6	120.4	C17—C16—H16	120.5
O3—C7—C8	124.26 (14)	C16—C17—C12	120.53 (13)
O3—C7—C6	114.75 (13)	C16—C17—H17	119.7
C8—C7—C6	120.98 (15)	C12—C17—H17	119.7
C7—C8—C9	120.61 (13)	O3—C18—H18A	109.5
C7—C8—H8	119.7	O3—C18—H18B	109.5
C9—C8—H8	119.7	H18A—C18—H18B	109.5
C8—C9—C10	118.02 (13)	O3—C18—H18C	109.5
C8—C9—C1	123.19 (12)	H18A—C18—H18C	109.5
C10—C9—C1	118.68 (13)	H18B—C18—H18C	109.5
C4—C10—C5	120.77 (14)
C9—C1—C2—O2	173.72 (13)	C6—C5—C10—C9	0.3 (2)
C11—C1—C2—O2	−7.2 (2)	C8—C9—C10—C4	174.23 (12)
C9—C1—C2—C3	−7.8 (2)	C1—C9—C10—C4	−2.23 (19)
C11—C1—C2—C3	171.28 (13)	C8—C9—C10—C5	−3.14 (19)
O2—C2—C3—C4	−177.98 (14)	C1—C9—C10—C5	−179.59 (12)
C1—C2—C3—C4	3.4 (2)	C2—C1—C11—O1	26.3 (2)
C2—C3—C4—C10	1.8 (2)	C9—C1—C11—O1	−154.68 (14)
C10—C5—C6—C7	1.6 (2)	C2—C1—C11—C12	−148.00 (14)
C18—O3—C7—C8	−0.5 (2)	C9—C1—C11—C12	31.0 (2)
C18—O3—C7—C6	179.99 (13)	O1—C11—C12—C17	−139.55 (14)
C5—C6—C7—O3	178.89 (13)	C1—C11—C12—C17	34.9 (2)
C5—C6—C7—C8	−0.6 (2)	O1—C11—C12—C13	33.95 (19)
O3—C7—C8—C9	178.21 (12)	C1—C11—C12—C13	−151.57 (13)
C6—C7—C8—C9	−2.4 (2)	C17—C12—C13—C14	−0.7 (2)
C7—C8—C9—C10	4.17 (19)	C11—C12—C13—C14	−174.37 (13)
C7—C8—C9—C1	−179.55 (13)	C12—C13—C14—C15	1.7 (2)
C2—C1—C9—C8	−169.18 (13)	C13—C14—C15—C16	−1.4 (2)
C11—C1—C9—C8	11.8 (2)	C13—C14—C15—Cl1	176.26 (11)
C2—C1—C9—C10	7.07 (19)	C14—C15—C16—C17	0.2 (2)
C11—C1—C9—C10	−171.92 (13)	Cl1—C15—C16—C17	−177.50 (11)
C3—C4—C10—C5	175.05 (14)	C15—C16—C17—C12	0.8 (2)
C3—C4—C10—C9	−2.3 (2)	C13—C12—C17—C16	−0.5 (2)
C6—C5—C10—C4	−177.05 (14)	C11—C12—C17—C16	172.96 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.94 (2)	1.71 (2)	2.5573 (16)	148 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.94 (2)	1.71 (2)	2.5573 (16)	148 (2)