(2-Hy-droxy-7-meth-oxy-naphthalen-1-yl)(phen-yl)methanone.

In the mol-ecule of the title compound, C(18)H(14)O(3), there is an intra-molecular O-H⋯O=C hydrogen bond between the carbonyl and hy-droxy groups on the naphthalene ring system. The angles between the C=O bond vector and the least-squares planes of the naphthalene ring system and the phenyl ring are 30.58 (6) and 42.82 (7)°, respectively, while the dihedral angle between the naphthalene ring system and the phenyl ring is 58.65 (5)°. In the crystal, mol-ecules are connected by pairs of inter-molecular O-H⋯O=C hydrogen bonds, forming centrosymmetric dimers.

Related literature

For closely related structures, see: Hijikata et al. (2010 ▶); Kato et al. (2010 ▶); Mitsui et al. (2009 ▶); Mitsui, Nakaema, Noguchi, Okamoto & Yonezawa (2008 ▶); Mitsui, Nakaema, Noguchi & Yonezawa (2008 ▶).

Experimental

Crystal data

C18H14O3

M = 278.29

Monoclinic,

a = 9.81012 (18) Å

b = 6.27891 (11) Å

c = 22.0737 (4) Å

β = 93.167 (1)°

V = 1357.59 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.75 mm−1

T = 193 K

0.60 × 0.40 × 0.40 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.586, T max = 0.754

20565 measured reflections

2496 independent reflections

2244 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.103

S = 1.08

2496 reflections

196 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.16 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/S1600536810038547/is2606sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038547/is2606Isup2.hkl

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

C18H14O3	F(000) = 584
Mr = 278.29	Dx = 1.362 Mg m−3
Monoclinic, P21/c	Melting point = 371.8–372.3 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54187 Å
a = 9.81012 (18) Å	Cell parameters from 19252 reflections
b = 6.27891 (11) Å	θ = 4.0–68.2°
c = 22.0737 (4) Å	µ = 0.75 mm−1
β = 93.167 (1)°	T = 193 K
V = 1357.59 (4) Å3	Block, yellow
Z = 4	0.60 × 0.40 × 0.40 mm

Rigaku R-AXIS RAPID diffractometer	2496 independent reflections
Radiation source: rotating anode	2244 reflections with I > 2σ(I)
graphite	Rint = 0.038
Detector resolution: 10.00 pixels mm-1	θmax = 68.2°, θmin = 4.0°
ω scans	h = −11→11
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −7→7
Tmin = 0.586, Tmax = 0.754	l = −26→26
20565 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)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103	w = 1/[σ2(Fo2) + (0.0535P)2 + 0.3346P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2496 reflections	Δρmax = 0.23 e Å−3
196 parameters	Δρmin = −0.16 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: 0.0146 (8)

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
O1	0.37752 (10)	0.17334 (19)	0.46905 (5)	0.0478 (3)
O2	0.84529 (10)	−0.02213 (17)	0.22739 (4)	0.0442 (3)
O3	0.57091 (10)	0.44133 (17)	0.45195 (5)	0.0482 (3)
C1	0.55482 (12)	0.1185 (2)	0.39823 (5)	0.0336 (3)
C2	0.43388 (13)	0.0609 (2)	0.42511 (6)	0.0387 (3)
C3	0.36518 (14)	−0.1302 (3)	0.40877 (7)	0.0451 (4)
H3	0.2846	−0.1684	0.4281	0.054*
C4	0.41359 (14)	−0.2593 (2)	0.36562 (7)	0.0431 (3)
H4	0.3685	−0.3902	0.3564	0.052*
C5	0.53019 (13)	−0.2030 (2)	0.33398 (6)	0.0363 (3)
C6	0.57599 (14)	−0.3323 (2)	0.28681 (6)	0.0407 (3)
H6	0.5321	−0.4647	0.2784	0.049*
C7	0.68125 (14)	−0.2718 (2)	0.25323 (6)	0.0401 (3)
H7	0.7113	−0.3612	0.2219	0.048*
C8	0.74557 (13)	−0.0737 (2)	0.26554 (6)	0.0356 (3)
C9	0.70639 (13)	0.0537 (2)	0.31195 (6)	0.0335 (3)
H9	0.7512	0.1860	0.3194	0.040*
C10	0.59982 (12)	−0.0095 (2)	0.34895 (5)	0.0322 (3)
C11	0.63086 (13)	0.3022 (2)	0.42425 (5)	0.0341 (3)
C12	0.78243 (13)	0.3247 (2)	0.42242 (5)	0.0327 (3)
C13	0.87010 (14)	0.1539 (2)	0.43450 (6)	0.0383 (3)
H13	0.8342	0.0163	0.4417	0.046*
C14	1.01009 (14)	0.1857 (2)	0.43590 (7)	0.0443 (4)
H14	1.0701	0.0698	0.4448	0.053*
C15	1.06297 (14)	0.3852 (3)	0.42446 (7)	0.0469 (4)
H15	1.1590	0.4054	0.4246	0.056*
C16	0.97576 (15)	0.5548 (2)	0.41281 (7)	0.0456 (4)
H16	1.0119	0.6917	0.4049	0.055*
C17	0.83608 (14)	0.5257 (2)	0.41259 (6)	0.0392 (3)
H17	0.7766	0.6437	0.4057	0.047*
C18	0.92146 (16)	0.1669 (3)	0.24071 (8)	0.0527 (4)
H18A	0.9894	0.1867	0.2103	0.063*
H18B	0.9679	0.1545	0.2810	0.063*
H18C	0.8595	0.2894	0.2400	0.063*
H1	0.428 (2)	0.296 (4)	0.4744 (11)	0.092 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0369 (5)	0.0601 (7)	0.0471 (6)	0.0032 (5)	0.0080 (4)	−0.0043 (5)
O2	0.0435 (5)	0.0478 (6)	0.0420 (5)	0.0003 (4)	0.0081 (4)	−0.0093 (4)
O3	0.0490 (6)	0.0453 (6)	0.0514 (6)	0.0042 (5)	0.0132 (5)	−0.0117 (5)
C1	0.0324 (6)	0.0356 (7)	0.0322 (6)	0.0041 (5)	−0.0032 (5)	0.0025 (5)
C2	0.0322 (6)	0.0468 (8)	0.0367 (7)	0.0046 (6)	−0.0011 (5)	0.0032 (6)
C3	0.0328 (7)	0.0543 (9)	0.0480 (8)	−0.0039 (6)	0.0004 (6)	0.0071 (7)
C4	0.0377 (7)	0.0415 (8)	0.0489 (8)	−0.0063 (6)	−0.0083 (6)	0.0064 (6)
C5	0.0349 (6)	0.0344 (7)	0.0384 (7)	0.0014 (5)	−0.0089 (5)	0.0028 (5)
C6	0.0409 (7)	0.0329 (7)	0.0466 (8)	−0.0003 (6)	−0.0116 (6)	−0.0035 (6)
C7	0.0422 (7)	0.0368 (7)	0.0402 (7)	0.0069 (6)	−0.0075 (6)	−0.0092 (6)
C8	0.0334 (6)	0.0389 (7)	0.0340 (6)	0.0055 (5)	−0.0030 (5)	−0.0017 (5)
C9	0.0340 (6)	0.0319 (7)	0.0340 (6)	0.0009 (5)	−0.0038 (5)	−0.0022 (5)
C10	0.0309 (6)	0.0327 (7)	0.0322 (6)	0.0041 (5)	−0.0061 (5)	0.0021 (5)
C11	0.0396 (7)	0.0343 (7)	0.0286 (6)	0.0055 (5)	0.0023 (5)	0.0011 (5)
C12	0.0376 (7)	0.0337 (7)	0.0265 (6)	0.0011 (5)	−0.0024 (5)	−0.0046 (5)
C13	0.0421 (7)	0.0337 (7)	0.0385 (7)	0.0010 (6)	−0.0040 (5)	−0.0017 (6)
C14	0.0406 (7)	0.0465 (8)	0.0449 (8)	0.0083 (6)	−0.0063 (6)	−0.0019 (6)
C15	0.0367 (7)	0.0582 (9)	0.0454 (8)	−0.0040 (7)	−0.0014 (6)	−0.0033 (7)
C16	0.0480 (8)	0.0428 (8)	0.0457 (8)	−0.0097 (6)	0.0001 (6)	0.0011 (6)
C17	0.0458 (8)	0.0333 (7)	0.0381 (7)	0.0025 (6)	−0.0031 (6)	−0.0023 (6)
C18	0.0512 (9)	0.0552 (10)	0.0531 (9)	−0.0099 (7)	0.0163 (7)	−0.0085 (7)

O1—C2	1.3434 (17)	C8—C9	1.3716 (18)
O1—H1	0.92 (2)	C9—C10	1.4184 (18)
O2—C8	1.3646 (16)	C9—H9	0.9500
O2—C18	1.4244 (18)	C11—C12	1.4964 (18)
O3—C11	1.2340 (16)	C12—C17	1.3895 (19)
C1—C2	1.4029 (18)	C12—C13	1.3908 (18)
C1—C10	1.4414 (18)	C13—C14	1.386 (2)
C1—C11	1.4728 (18)	C13—H13	0.9500
C2—C3	1.413 (2)	C14—C15	1.384 (2)
C3—C4	1.357 (2)	C14—H14	0.9500
C3—H3	0.9500	C15—C16	1.381 (2)
C4—C5	1.418 (2)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.382 (2)
C5—C6	1.413 (2)	C16—H16	0.9500
C5—C10	1.4233 (18)	C17—H17	0.9500
C6—C7	1.358 (2)	C18—H18A	0.9800
C6—H6	0.9500	C18—H18B	0.9800
C7—C8	1.4138 (19)	C18—H18C	0.9800
C7—H7	0.9500
C2—O1—H1	107.2 (15)	C9—C10—C1	123.00 (12)
C8—O2—C18	117.15 (11)	C5—C10—C1	119.21 (11)
C2—C1—C10	118.47 (12)	O3—C11—C1	120.18 (12)
C2—C1—C11	117.33 (12)	O3—C11—C12	116.62 (12)
C10—C1—C11	124.15 (11)	C1—C11—C12	123.10 (11)
O1—C2—C1	124.13 (13)	C17—C12—C13	119.65 (12)
O1—C2—C3	114.90 (12)	C17—C12—C11	118.39 (11)
C1—C2—C3	120.91 (13)	C13—C12—C11	121.80 (12)
C4—C3—C2	120.41 (13)	C14—C13—C12	119.65 (13)
C4—C3—H3	119.8	C14—C13—H13	120.2
C2—C3—H3	119.8	C12—C13—H13	120.2
C3—C4—C5	121.32 (13)	C15—C14—C13	120.45 (13)
C3—C4—H4	119.3	C15—C14—H14	119.8
C5—C4—H4	119.3	C13—C14—H14	119.8
C6—C5—C4	121.16 (13)	C16—C15—C14	119.80 (13)
C6—C5—C10	119.56 (12)	C16—C15—H15	120.1
C4—C5—C10	119.26 (13)	C14—C15—H15	120.1
C7—C6—C5	121.57 (13)	C15—C16—C17	120.20 (14)
C7—C6—H6	119.2	C15—C16—H16	119.9
C5—C6—H6	119.2	C17—C16—H16	119.9
C6—C7—C8	119.07 (13)	C16—C17—C12	120.21 (13)
C6—C7—H7	120.5	C16—C17—H17	119.9
C8—C7—H7	120.5	C12—C17—H17	119.9
O2—C8—C9	124.22 (12)	O2—C18—H18A	109.5
O2—C8—C7	114.70 (12)	O2—C18—H18B	109.5
C9—C8—C7	121.07 (12)	H18A—C18—H18B	109.5
C8—C9—C10	120.84 (12)	O2—C18—H18C	109.5
C8—C9—H9	119.6	H18A—C18—H18C	109.5
C10—C9—H9	119.6	H18B—C18—H18C	109.5
C9—C10—C5	117.70 (12)
C10—C1—C2—O1	−176.30 (12)	C6—C5—C10—C1	−178.29 (11)
C11—C1—C2—O1	6.22 (19)	C4—C5—C10—C1	3.48 (18)
C10—C1—C2—C3	6.53 (19)	C2—C1—C10—C9	168.90 (12)
C11—C1—C2—C3	−170.95 (12)	C11—C1—C10—C9	−13.80 (19)
O1—C2—C3—C4	−178.91 (13)	C2—C1—C10—C5	−7.45 (17)
C1—C2—C3—C4	−1.5 (2)	C11—C1—C10—C5	169.85 (11)
C2—C3—C4—C5	−2.7 (2)	C2—C1—C11—O3	−25.19 (18)
C3—C4—C5—C6	−176.55 (13)	C10—C1—C11—O3	157.48 (12)
C3—C4—C5—C10	1.7 (2)	C2—C1—C11—C12	150.82 (12)
C4—C5—C6—C7	175.00 (13)	C10—C1—C11—C12	−26.50 (18)
C10—C5—C6—C7	−3.20 (19)	O3—C11—C12—C17	−42.07 (17)
C5—C6—C7—C8	−0.6 (2)	C1—C11—C12—C17	141.79 (12)
C18—O2—C8—C9	6.22 (19)	O3—C11—C12—C13	133.31 (13)
C18—O2—C8—C7	−174.85 (12)	C1—C11—C12—C13	−42.84 (18)
C6—C7—C8—O2	−176.72 (12)	C17—C12—C13—C14	−0.74 (19)
C6—C7—C8—C9	2.25 (19)	C11—C12—C13—C14	−176.06 (12)
O2—C8—C9—C10	178.76 (11)	C12—C13—C14—C15	−1.0 (2)
C7—C8—C9—C10	−0.11 (19)	C13—C14—C15—C16	1.4 (2)
C8—C9—C10—C5	−3.58 (18)	C14—C15—C16—C17	0.0 (2)
C8—C9—C10—C1	−179.98 (11)	C15—C16—C17—C12	−1.8 (2)
C6—C5—C10—C9	5.17 (17)	C13—C12—C17—C16	2.1 (2)
C4—C5—C10—C9	−173.06 (12)	C11—C12—C17—C16	177.61 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.92 (2)	1.77 (2)	2.5792 (14)	145 (2)
O1—H1···O3i	0.92 (2)	2.32 (2)	3.0088 (16)	132.4 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3	0.92 (2)	1.77 (2)	2.5792 (14)	145 (2)
O1—H1⋯O3i	0.92 (2)	2.32 (2)	3.0088 (16)	132.4 (18)

Symmetry code: (i) .