(3,6-Dimeth-oxy-naphthalen-2-yl)(phen-yl)methanone.

In the title compound, C(19)H(16)O(3), the dihedral angle between the naphthalene ring system and the phenyl ring is 68.32 (5)°. The bridging carbonyl C-C(=O)-C plane makes a dihedral angle of 54.32 (5)° with the naphthalene ring system and 21.45 (6)° with the phenyl ring. An inter-molecular C-H⋯O hydrogen bond exists between the H atom of one meth-oxy group and the O atom of the second meth-oxy group in an adjacent mol-ecule. The crystal packing is additionally stabilized by a weak C-H⋯O inter-molecular inter-action between an H atom of the naphthalene ring and the O atom of the carbonyl group.

Related literature

For electrophilic aromatic substitution of naphthalene deriv­atives affording peri-aroylated compounds regioselectively, see: Okamoto & Yonezawa (2009 ▶). For the structures of closely related compounds, see: Kataoka et al. (2010 ▶); Kato et al. (2010 ▶); Muto et al. (2010 ▶); Nakaema, Okamoto et al. (2008 ▶); Nakaema, Watanabe et al. (2008 ▶); Nishijima et al. (2010 ▶); Watanabe et al. (2010 ▶).

Experimental

Crystal data

C19H16O3

M = 292.32

Monoclinic,

a = 8.7186 (2) Å

b = 20.4650 (4) Å

c = 8.5675 (2) Å

β = 102.475 (1)°

V = 1492.57 (6) Å3

Z = 4

Cu Kα radiation

μ = 0.71 mm−1

T = 193 K

0.60 × 0.50 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.677, T max = 0.872

26682 measured reflections

2735 independent reflections

2509 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.098

S = 1.06

2735 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.17 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2010 ▶); program(s) used to solve structure: Il Milione (Burla et al., 2007 ▶); 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 I, global. DOI: 10.1107/S1600536811005630/fk2037sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005630/fk2037Isup2.hkl

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

C19H16O3	F(000) = 616
Mr = 292.32	Dx = 1.301 Mg m−3
Monoclinic, P21/c	Melting point = 438.7–441.5 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54187 Å
a = 8.7186 (2) Å	Cell parameters from 16018 reflections
b = 20.4650 (4) Å	θ = 4.3–68.2°
c = 8.5675 (2) Å	µ = 0.71 mm−1
β = 102.475 (1)°	T = 193 K
V = 1492.57 (6) Å3	Platelet, colorless
Z = 4	0.60 × 0.50 × 0.20 mm

Rigaku R-AXIS RAPID diffractometer	2735 independent reflections
Radiation source: rotating anode	2509 reflections with I > 2σ(I)
graphite	Rint = 0.044
Detector resolution: 10.000 pixels mm-1	θmax = 68.2°, θmin = 4.3°
ω scans	h = −10→10
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −24→24
Tmin = 0.677, Tmax = 0.872	l = −10→10
26682 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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0584P)2 + 0.2227P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2735 reflections	Δρmax = 0.23 e Å−3
202 parameters	Δρmin = −0.17 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: 0.0131 (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	0.78878 (10)	0.03272 (4)	0.31564 (10)	0.0421 (2)
O2	0.82137 (9)	0.20198 (4)	0.16422 (9)	0.0365 (2)
O3	1.49637 (9)	0.28351 (4)	0.80270 (10)	0.0420 (2)
C1	1.04784 (12)	0.23386 (5)	0.36717 (13)	0.0299 (2)
H1	1.0346	0.2786	0.3379	0.036*
C2	0.94725 (12)	0.18810 (5)	0.28459 (13)	0.0297 (2)
C3	0.96544 (12)	0.12068 (5)	0.32677 (12)	0.0301 (2)
C4	1.08301 (13)	0.10241 (5)	0.45329 (12)	0.0314 (3)
H4	1.0931	0.0577	0.4834	0.038*
C5	1.18928 (12)	0.14824 (5)	0.53981 (12)	0.0307 (3)
C6	1.31320 (13)	0.13009 (5)	0.66941 (13)	0.0361 (3)
H6	1.3272	0.0854	0.6992	0.043*
C7	1.41212 (13)	0.17582 (6)	0.75144 (14)	0.0378 (3)
H7	1.4948	0.1629	0.8374	0.045*
C8	1.39183 (12)	0.24263 (6)	0.70863 (13)	0.0335 (3)
C9	1.27567 (12)	0.26199 (5)	0.58315 (13)	0.0314 (3)
H9	1.2648	0.3069	0.5544	0.038*
C10	1.17134 (12)	0.21514 (5)	0.49575 (12)	0.0288 (2)
C11	0.85594 (12)	0.06982 (5)	0.24066 (13)	0.0312 (2)
C12	0.83398 (13)	0.06328 (5)	0.06375 (13)	0.0320 (3)
C13	0.94512 (15)	0.08664 (5)	−0.01647 (14)	0.0386 (3)
H13	1.0356	0.1089	0.0408	0.046*
C14	0.92417 (18)	0.07753 (6)	−0.18018 (15)	0.0495 (3)
H14	1.0017	0.0925	−0.2343	0.059*
C15	0.7911 (2)	0.04677 (6)	−0.26460 (16)	0.0550 (4)
H15	0.7757	0.0418	−0.3772	0.066*
C16	0.67992 (18)	0.02314 (7)	−0.18521 (16)	0.0546 (4)
H16	0.5884	0.0018	−0.2432	0.066*
C17	0.70235 (15)	0.03068 (6)	−0.02102 (15)	0.0436 (3)
H17	0.6274	0.0135	0.0337	0.052*
C18	0.78092 (13)	0.26937 (5)	0.13734 (15)	0.0371 (3)
H18A	0.7644	0.2890	0.2367	0.044*
H18B	0.6843	0.2730	0.0545	0.044*
H18C	0.8663	0.2923	0.1024	0.044*
C19	1.47866 (16)	0.35166 (6)	0.77225 (16)	0.0468 (3)
H19A	1.4949	0.3611	0.6648	0.056*
H19B	1.5563	0.3757	0.8514	0.056*
H19C	1.3727	0.3652	0.7795	0.056*

	U11	U22	U33	U12	U13	U23
O1	0.0504 (5)	0.0376 (4)	0.0393 (5)	−0.0111 (4)	0.0122 (4)	0.0032 (3)
O2	0.0385 (4)	0.0293 (4)	0.0366 (4)	0.0020 (3)	−0.0034 (3)	−0.0004 (3)
O3	0.0390 (5)	0.0418 (5)	0.0411 (5)	−0.0081 (3)	−0.0008 (4)	−0.0024 (4)
C1	0.0344 (5)	0.0250 (5)	0.0309 (6)	0.0011 (4)	0.0086 (4)	0.0016 (4)
C2	0.0317 (5)	0.0303 (5)	0.0273 (5)	0.0022 (4)	0.0067 (4)	0.0012 (4)
C3	0.0344 (5)	0.0282 (5)	0.0291 (5)	−0.0002 (4)	0.0095 (4)	−0.0009 (4)
C4	0.0376 (6)	0.0267 (5)	0.0308 (6)	0.0017 (4)	0.0096 (5)	0.0024 (4)
C5	0.0327 (5)	0.0311 (5)	0.0293 (5)	0.0015 (4)	0.0091 (4)	0.0016 (4)
C6	0.0387 (6)	0.0333 (6)	0.0353 (6)	0.0025 (4)	0.0053 (5)	0.0056 (4)
C7	0.0348 (6)	0.0421 (6)	0.0341 (6)	0.0019 (5)	0.0022 (5)	0.0048 (5)
C8	0.0305 (5)	0.0392 (6)	0.0314 (6)	−0.0038 (4)	0.0079 (4)	−0.0028 (4)
C9	0.0329 (5)	0.0298 (5)	0.0324 (6)	−0.0009 (4)	0.0093 (4)	0.0000 (4)
C10	0.0298 (5)	0.0305 (5)	0.0278 (5)	0.0005 (4)	0.0099 (4)	0.0000 (4)
C11	0.0330 (5)	0.0262 (5)	0.0345 (6)	0.0018 (4)	0.0076 (4)	0.0019 (4)
C12	0.0375 (6)	0.0243 (5)	0.0330 (6)	0.0023 (4)	0.0053 (4)	−0.0010 (4)
C13	0.0491 (7)	0.0298 (5)	0.0386 (6)	−0.0008 (5)	0.0135 (5)	−0.0006 (5)
C14	0.0766 (9)	0.0365 (6)	0.0407 (7)	0.0071 (6)	0.0247 (7)	0.0016 (5)
C15	0.0892 (11)	0.0407 (7)	0.0322 (7)	0.0188 (7)	0.0062 (7)	−0.0044 (5)
C16	0.0614 (8)	0.0492 (8)	0.0447 (8)	0.0046 (6)	−0.0076 (6)	−0.0125 (6)
C17	0.0428 (6)	0.0416 (6)	0.0438 (7)	−0.0027 (5)	0.0034 (5)	−0.0060 (5)
C18	0.0373 (6)	0.0318 (6)	0.0390 (6)	0.0040 (4)	0.0014 (5)	0.0045 (4)
C19	0.0488 (7)	0.0413 (7)	0.0480 (7)	−0.0118 (5)	0.0053 (6)	−0.0059 (5)

O1—C11	1.2224 (13)	C9—C10	1.4188 (15)
O2—C2	1.3637 (13)	C9—H9	0.9500
O2—C18	1.4299 (13)	C11—C12	1.4921 (15)
O3—C8	1.3649 (13)	C12—C13	1.3884 (16)
O3—C19	1.4211 (15)	C12—C17	1.3891 (16)
C1—C2	1.3706 (15)	C13—C14	1.3873 (17)
C1—C10	1.4168 (15)	C13—H13	0.9500
C1—H1	0.9500	C14—C15	1.379 (2)
C2—C3	1.4265 (14)	C14—H14	0.9500
C3—C4	1.3731 (15)	C15—C16	1.386 (2)
C3—C11	1.4948 (15)	C15—H15	0.9500
C4—C5	1.4110 (15)	C16—C17	1.3864 (18)
C4—H4	0.9500	C16—H16	0.9500
C5—C10	1.4198 (14)	C17—H17	0.9500
C5—C6	1.4212 (15)	C18—H18A	0.9800
C6—C7	1.3607 (17)	C18—H18B	0.9800
C6—H6	0.9500	C18—H18C	0.9800
C7—C8	1.4166 (16)	C19—H19A	0.9800
C7—H7	0.9500	C19—H19B	0.9800
C8—C9	1.3668 (16)	C19—H19C	0.9800
C2—O2—C18	116.93 (8)	O1—C11—C3	120.03 (10)
C8—O3—C19	117.45 (9)	C12—C11—C3	119.46 (9)
C2—C1—C10	120.71 (9)	C13—C12—C17	119.52 (11)
C2—C1—H1	119.6	C13—C12—C11	121.46 (10)
C10—C1—H1	119.6	C17—C12—C11	118.97 (10)
O2—C2—C1	124.67 (9)	C14—C13—C12	120.04 (12)
O2—C2—C3	114.85 (9)	C14—C13—H13	120.0
C1—C2—C3	120.42 (10)	C12—C13—H13	120.0
C4—C3—C2	119.11 (10)	C15—C14—C13	120.24 (13)
C4—C3—C11	119.23 (9)	C15—C14—H14	119.9
C2—C3—C11	121.62 (9)	C13—C14—H14	119.9
C3—C4—C5	121.82 (10)	C14—C15—C16	120.00 (12)
C3—C4—H4	119.1	C14—C15—H15	120.0
C5—C4—H4	119.1	C16—C15—H15	120.0
C4—C5—C10	118.63 (10)	C15—C16—C17	119.92 (13)
C4—C5—C6	122.61 (10)	C15—C16—H16	120.0
C10—C5—C6	118.76 (10)	C17—C16—H16	120.0
C7—C6—C5	120.92 (10)	C16—C17—C12	120.23 (12)
C7—C6—H6	119.5	C16—C17—H17	119.9
C5—C6—H6	119.5	C12—C17—H17	119.9
C6—C7—C8	120.02 (10)	O2—C18—H18A	109.5
C6—C7—H7	120.0	O2—C18—H18B	109.5
C8—C7—H7	120.0	H18A—C18—H18B	109.5
O3—C8—C9	125.00 (10)	O2—C18—H18C	109.5
O3—C8—C7	114.12 (10)	H18A—C18—H18C	109.5
C9—C8—C7	120.88 (10)	H18B—C18—H18C	109.5
C8—C9—C10	120.06 (10)	O3—C19—H19A	109.5
C8—C9—H9	120.0	O3—C19—H19B	109.5
C10—C9—H9	120.0	H19A—C19—H19B	109.5
C1—C10—C9	121.37 (10)	O3—C19—H19C	109.5
C1—C10—C5	119.28 (10)	H19A—C19—H19C	109.5
C9—C10—C5	119.34 (10)	H19B—C19—H19C	109.5
O1—C11—C12	120.47 (10)
C18—O2—C2—C1	−8.42 (15)	C8—C9—C10—C1	178.71 (10)
C18—O2—C2—C3	168.77 (9)	C8—C9—C10—C5	−0.15 (15)
C10—C1—C2—O2	176.97 (9)	C4—C5—C10—C1	0.12 (15)
C10—C1—C2—C3	−0.07 (16)	C6—C5—C10—C1	−179.74 (9)
O2—C2—C3—C4	−175.98 (9)	C4—C5—C10—C9	179.01 (9)
C1—C2—C3—C4	1.34 (16)	C6—C5—C10—C9	−0.85 (15)
O2—C2—C3—C11	1.64 (14)	C4—C3—C11—O1	51.76 (14)
C1—C2—C3—C11	178.96 (9)	C2—C3—C11—O1	−125.86 (11)
C2—C3—C4—C5	−1.91 (16)	C4—C3—C11—C12	−126.07 (10)
C11—C3—C4—C5	−179.58 (9)	C2—C3—C11—C12	56.32 (14)
C3—C4—C5—C10	1.18 (16)	O1—C11—C12—C13	−156.48 (11)
C3—C4—C5—C6	−178.96 (10)	C3—C11—C12—C13	21.34 (15)
C4—C5—C6—C7	−179.10 (10)	O1—C11—C12—C17	20.86 (15)
C10—C5—C6—C7	0.75 (16)	C3—C11—C12—C17	−161.33 (10)
C5—C6—C7—C8	0.35 (17)	C17—C12—C13—C14	0.16 (17)
C19—O3—C8—C9	2.94 (16)	C11—C12—C13—C14	177.48 (10)
C19—O3—C8—C7	−176.95 (10)	C12—C13—C14—C15	1.68 (18)
C6—C7—C8—O3	178.50 (10)	C13—C14—C15—C16	−1.88 (19)
C6—C7—C8—C9	−1.40 (17)	C14—C15—C16—C17	0.2 (2)
O3—C8—C9—C10	−178.60 (9)	C15—C16—C17—C12	1.61 (19)
C7—C8—C9—C10	1.28 (16)	C13—C12—C17—C16	−1.80 (17)
C2—C1—C10—C9	−179.52 (9)	C11—C12—C17—C16	−179.19 (11)
C2—C1—C10—C5	−0.65 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1i	0.95	2.58	3.4439 (13)	151
C18—H18B···O3ii	0.98	2.42	3.3742 (15)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1i	0.95	2.58	3.4439 (13)	151
C18—H18B⋯O3ii	0.98	2.42	3.3742 (15)	164

Symmetry codes: (i) ; (ii) .