(2-Hy-droxy-7-meth-oxy-naphthalen-1-yl)(4-methyl-phen-yl)methanone.

In the title compound, C(19)H(16)O(3), an intra-molecular O-H⋯O=C hydrogen bond is formed between the hy-droxy and carbonyl groups on the naphthalene ring system, resulting in an S(6) ring. The angles between the C=O bond vector and the least-squares planes of the naphthalene ring system and the benzene ring are 27.63 (6) and 47.99 (7)°, respectively. The dihedral angle between the latter planes is 61.39 (5)°. In the crystal, two mol-ecules are connected by pairs of inter-molecular O-H⋯O=C hydrogen bonds, forming centrosymmetric dimers with an R(2) (2)(4) graph-set motif. The mol-ecular packing features C-H⋯π interactions.

Related literature

For electrophilic aromatic substitution of naphthalene deriva­­tives, see: Okamoto & Yonezawa (2009 ▶). For the structures of closely related compounds, see: Mitsui et al. (2008 ▶); Nagasawa et al. (2010a ▶,b ▶,c ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶); Etter et al. (1990 ▶).

Experimental

Crystal data

C19H16O3

M = 292.32

Monoclinic,

a = 11.1599 (2) Å

b = 6.05387 (11) Å

c = 22.0153 (4) Å

β = 90.317 (1)°

V = 1487.35 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.71 mm−1

T = 193 K

0.60 × 0.50 × 0.30 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.676, T max = 0.816

25155 measured reflections

2729 independent reflections

2493 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.106

S = 1.04

2729 reflections

204 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.15 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 ▶), ORTEP -3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810040614/dn2608sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040614/dn2608Isup2.hkl

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

C19H16O3	F(000) = 616
Mr = 292.32	Dx = 1.305 Mg m−3
Monoclinic, P21/c	Melting point = 385.5–386.0 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54187 Å
a = 11.1599 (2) Å	Cell parameters from 21159 reflections
b = 6.05387 (11) Å	θ = 4.0–68.2°
c = 22.0153 (4) Å	µ = 0.71 mm−1
β = 90.317 (1)°	T = 193 K
V = 1487.35 (5) Å3	Block, colorless
Z = 4	0.60 × 0.50 × 0.30 mm

Rigaku R-AXIS RAPID diffractometer	2729 independent reflections
Radiation source: rotating anode	2493 reflections with I > 2σ(I)
graphite	Rint = 0.029
Detector resolution: 10.00 pixels mm-1	θmax = 68.2°, θmin = 4.0°
ω scans	h = −13→13
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −7→7
Tmin = 0.676, Tmax = 0.816	l = −26→26
25155 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0563P)2 + 0.4274P] where P = (Fo2 + 2Fc2)/3
2729 reflections	(Δ/σ)max < 0.001
204 parameters	Δρmax = 0.28 e Å−3
1 restraint	Δρmin = −0.15 e Å−3

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
O1	0.39263 (8)	0.16739 (19)	0.46840 (5)	0.0479 (3)
H1	0.4401 (16)	0.298 (3)	0.4719 (9)	0.072*
O2	0.83634 (10)	−0.07553 (19)	0.23277 (5)	0.0539 (3)
O3	0.56764 (8)	0.43447 (17)	0.45225 (4)	0.0464 (3)
C1	0.55371 (10)	0.1035 (2)	0.39700 (5)	0.0324 (3)
C2	0.44354 (11)	0.0500 (2)	0.42366 (6)	0.0391 (3)
C3	0.38007 (12)	−0.1414 (3)	0.40634 (7)	0.0476 (4)
H3	0.3062	−0.1761	0.4254	0.057*
C4	0.42384 (12)	−0.2755 (3)	0.36282 (7)	0.0473 (4)
H4	0.3814	−0.4065	0.3527	0.057*
C5	0.53176 (12)	−0.2259 (2)	0.33185 (6)	0.0390 (3)
C6	0.57478 (13)	−0.3633 (2)	0.28499 (6)	0.0456 (4)
H6	0.5324	−0.4947	0.2752	0.055*
C7	0.67500 (14)	−0.3123 (2)	0.25359 (6)	0.0473 (4)
H7	0.7032	−0.4082	0.2226	0.057*
C8	0.73726 (12)	−0.1148 (2)	0.26736 (6)	0.0401 (3)
C9	0.69806 (11)	0.0239 (2)	0.31228 (5)	0.0344 (3)
H9	0.7394	0.1584	0.3198	0.041*
C10	0.59639 (11)	−0.0312 (2)	0.34765 (5)	0.0325 (3)
C11	0.62050 (10)	0.2897 (2)	0.42351 (5)	0.0316 (3)
C12	0.75391 (10)	0.3095 (2)	0.42076 (5)	0.0297 (3)
C13	0.82996 (11)	0.1359 (2)	0.43596 (5)	0.0340 (3)
H13	0.7978	−0.0045	0.4462	0.041*
C14	0.95292 (11)	0.1683 (2)	0.43615 (6)	0.0385 (3)
H14	1.0042	0.0491	0.4468	0.046*
C15	1.00296 (11)	0.3713 (2)	0.42111 (6)	0.0386 (3)
C16	0.92554 (12)	0.5426 (2)	0.40584 (6)	0.0399 (3)
H16	0.9577	0.6822	0.3949	0.048*
C17	0.80264 (11)	0.5137 (2)	0.40630 (6)	0.0349 (3)
H17	0.7513	0.6341	0.3967	0.042*
C18	0.90578 (16)	0.1156 (3)	0.24644 (8)	0.0635 (5)
H18A	0.8577	0.2483	0.2389	0.095*
H18B	0.9770	0.1183	0.2206	0.095*
H18C	0.9304	0.1118	0.2892	0.095*
C19	1.13644 (12)	0.4059 (3)	0.42216 (7)	0.0555 (4)
H19A	1.1608	0.4843	0.3853	0.083*
H19B	1.1769	0.2623	0.4240	0.083*
H19C	1.1586	0.4935	0.4579	0.083*

	U11	U22	U33	U12	U13	U23
O1	0.0303 (5)	0.0623 (7)	0.0510 (6)	0.0003 (4)	0.0060 (4)	0.0009 (5)
O2	0.0604 (6)	0.0584 (7)	0.0431 (5)	0.0026 (5)	0.0108 (5)	−0.0121 (5)
O3	0.0406 (5)	0.0471 (6)	0.0514 (6)	0.0026 (4)	0.0110 (4)	−0.0114 (5)
C1	0.0291 (6)	0.0354 (7)	0.0327 (6)	0.0000 (5)	−0.0054 (5)	0.0051 (5)
C2	0.0296 (6)	0.0481 (8)	0.0396 (7)	−0.0002 (6)	−0.0050 (5)	0.0082 (6)
C3	0.0324 (7)	0.0561 (9)	0.0541 (8)	−0.0112 (6)	−0.0057 (6)	0.0105 (7)
C4	0.0416 (7)	0.0441 (8)	0.0560 (8)	−0.0145 (6)	−0.0166 (6)	0.0096 (7)
C5	0.0435 (7)	0.0334 (7)	0.0398 (7)	−0.0028 (6)	−0.0157 (5)	0.0046 (5)
C6	0.0557 (9)	0.0342 (7)	0.0466 (8)	−0.0024 (6)	−0.0201 (6)	−0.0019 (6)
C7	0.0633 (9)	0.0395 (8)	0.0389 (7)	0.0102 (7)	−0.0136 (6)	−0.0106 (6)
C8	0.0470 (7)	0.0423 (8)	0.0309 (6)	0.0055 (6)	−0.0032 (5)	−0.0022 (5)
C9	0.0398 (7)	0.0318 (6)	0.0314 (6)	−0.0002 (5)	−0.0057 (5)	−0.0008 (5)
C10	0.0333 (6)	0.0318 (6)	0.0322 (6)	0.0004 (5)	−0.0096 (5)	0.0043 (5)
C11	0.0321 (6)	0.0348 (6)	0.0281 (6)	0.0017 (5)	0.0015 (4)	0.0013 (5)
C12	0.0318 (6)	0.0309 (6)	0.0263 (5)	−0.0006 (5)	−0.0018 (4)	−0.0041 (5)
C13	0.0373 (6)	0.0297 (6)	0.0350 (6)	−0.0010 (5)	−0.0019 (5)	0.0011 (5)
C14	0.0364 (7)	0.0419 (7)	0.0371 (6)	0.0080 (6)	−0.0061 (5)	0.0001 (5)
C15	0.0331 (6)	0.0498 (8)	0.0330 (6)	−0.0039 (6)	−0.0020 (5)	−0.0047 (6)
C16	0.0407 (7)	0.0354 (7)	0.0436 (7)	−0.0088 (6)	−0.0003 (5)	−0.0008 (6)
C17	0.0377 (7)	0.0293 (6)	0.0377 (6)	0.0008 (5)	−0.0033 (5)	−0.0015 (5)
C18	0.0617 (10)	0.0691 (11)	0.0600 (10)	−0.0069 (9)	0.0244 (8)	−0.0082 (8)
C19	0.0334 (7)	0.0789 (12)	0.0542 (9)	−0.0074 (7)	−0.0031 (6)	−0.0031 (8)

O1—C2	1.3433 (17)	C9—C10	1.4195 (18)
O1—H1	0.953 (15)	C9—H9	0.9500
O2—C8	1.3670 (17)	C11—C12	1.4953 (16)
O2—C18	1.424 (2)	C12—C17	1.3885 (18)
O3—C11	1.2332 (15)	C12—C13	1.3907 (17)
C1—C2	1.4031 (17)	C13—C14	1.3862 (18)
C1—C10	1.4414 (18)	C13—H13	0.9500
C1—C11	1.4704 (17)	C14—C15	1.390 (2)
C2—C3	1.410 (2)	C14—H14	0.9500
C3—C4	1.349 (2)	C15—C16	1.390 (2)
C3—H3	0.9500	C15—C19	1.5043 (18)
C4—C5	1.420 (2)	C16—C17	1.3827 (18)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.411 (2)	C17—H17	0.9500
C5—C10	1.4237 (18)	C18—H18A	0.9800
C6—C7	1.354 (2)	C18—H18B	0.9800
C6—H6	0.9500	C18—H18C	0.9800
C7—C8	1.415 (2)	C19—H19A	0.9800
C7—H7	0.9500	C19—H19B	0.9800
C8—C9	1.3708 (18)	C19—H19C	0.9800
C2—O1—H1	105.1 (11)	O3—C11—C12	116.30 (11)
C8—O2—C18	117.68 (11)	C1—C11—C12	123.23 (11)
C2—C1—C10	118.60 (12)	C17—C12—C13	119.27 (11)
C2—C1—C11	117.02 (11)	C17—C12—C11	118.17 (11)
C10—C1—C11	124.33 (11)	C13—C12—C11	122.42 (11)
O1—C2—C1	124.04 (12)	C14—C13—C12	119.75 (12)
O1—C2—C3	114.79 (12)	C14—C13—H13	120.1
C1—C2—C3	121.11 (13)	C12—C13—H13	120.1
C4—C3—C2	120.21 (13)	C13—C14—C15	121.57 (12)
C4—C3—H3	119.9	C13—C14—H14	119.2
C2—C3—H3	119.9	C15—C14—H14	119.2
C3—C4—C5	121.68 (13)	C16—C15—C14	117.84 (12)
C3—C4—H4	119.2	C16—C15—C19	120.94 (13)
C5—C4—H4	119.2	C14—C15—C19	121.22 (13)
C6—C5—C4	121.28 (13)	C17—C16—C15	121.28 (12)
C6—C5—C10	119.50 (13)	C17—C16—H16	119.4
C4—C5—C10	119.21 (13)	C15—C16—H16	119.4
C7—C6—C5	121.63 (13)	C16—C17—C12	120.26 (12)
C7—C6—H6	119.2	C16—C17—H17	119.9
C5—C6—H6	119.2	C12—C17—H17	119.9
C6—C7—C8	119.29 (13)	O2—C18—H18A	109.5
C6—C7—H7	120.4	O2—C18—H18B	109.5
C8—C7—H7	120.4	H18A—C18—H18B	109.5
O2—C8—C9	123.90 (13)	O2—C18—H18C	109.5
O2—C8—C7	115.18 (12)	H18A—C18—H18C	109.5
C9—C8—C7	120.92 (13)	H18B—C18—H18C	109.5
C8—C9—C10	120.74 (12)	C15—C19—H19A	109.5
C8—C9—H9	119.6	C15—C19—H19B	109.5
C10—C9—H9	119.6	H19A—C19—H19B	109.5
C9—C10—C5	117.76 (12)	C15—C19—H19C	109.5
C9—C10—C1	123.31 (11)	H19A—C19—H19C	109.5
C5—C10—C1	118.90 (12)	H19B—C19—H19C	109.5
O3—C11—C1	120.38 (11)

CT1 and CT2 are the centroids of the C5–C10 and C12-C17 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.95 (2)	1.70 (2)	2.5618 (14)	148 (2)
O1—H1···O3i	0.95 (2)	2.33 (2)	3.0083 (16)	128 (1)
C6—H6···CT1ii	0.95	2.71	3.5203 (13)	144
C17—H17···CT1iii	0.95	2.76	3.5492 (12)	141
C19—H19C···CT2iv	0.98	2.88	3.7834 (16)	154

Table 1

Hydrogen-bond geometry (Å, °)

CT1 and CT2 are the centroids of the C5–C10 and C12–C17 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3	0.95 (2)	1.70 (2)	2.5618 (14)	148 (2)
O1—H1⋯O3i	0.95 (2)	2.33 (2)	3.0083 (16)	128 (1)
C6—H6⋯CT1ii	0.95	2.71	3.5203 (13)	144
C17—H17⋯CT1iii	0.95	2.76	3.5492 (12)	141
C19—H19C⋯CT2iv	0.98	2.88	3.7834 (16)	154

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .