(2,7-Dimeth-oxy-naphthalen-1-yl)(4-phen-oxy-phen-yl)methanone.

In the title mol-ecule, C25H20O4, the naphthalene and phen-oxy groups are oriented nearly perpendicular with respect to the benzene ring of the benzoyl group, with dihedral angles of 89.61 (5) and 86.13 (6)°, respectively. The crystal structure features C-H⋯O and C-H⋯π inter-actions.

Related literature

For the formation reactions of aroylated naphthalene compounds via electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009 ▶); Okamoto et al. (2011 ▶). For the structures of closely related compounds, see: Hijikata et al. (2010 ▶); Nakaema et al. (2008 ▶); Sasagawa et al. (2013 ▶); Tsumuki et al. (2011 ▶, 2012 ▶).

Experimental

Crystal data

C25H20O4

M = 384.41

Monoclinic,

a = 10.9512 (2) Å

b = 15.8830 (3) Å

c = 11.2184 (2) Å

β = 92.460 (1)°

V = 1949.51 (6) Å3

Z = 4

Cu Kα radiation

μ = 0.71 mm−1

T = 193 K

0.60 × 0.40 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.674, T max = 0.871

35423 measured reflections

3551 independent reflections

3228 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.097

S = 1.05

3551 reflections

265 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.16 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813004820/gk2553sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004820/gk2553Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813004820/gk2553Isup3.cml

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

C25H20O4	F(000) = 808
Mr = 384.41	Dx = 1.310 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2yn	Cell parameters from 30559 reflections
a = 10.9512 (2) Å	θ = 3.9–68.2°
b = 15.8830 (3) Å	µ = 0.71 mm−1
c = 11.2184 (2) Å	T = 193 K
β = 92.460 (1)°	Block, colourless
V = 1949.51 (6) Å3	0.60 × 0.40 × 0.20 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	3551 independent reflections
Radiation source: fine-focus sealed tube	3228 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
Detector resolution: 10.000 pixels mm-1	θmax = 68.2°, θmin = 4.8°
ω scans	h = −13→13
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −18→17
Tmin = 0.674, Tmax = 0.871	l = −13→13
35423 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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0483P)2 + 0.525P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3551 reflections	Δρmax = 0.21 e Å−3
265 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: 0.0082 (4)

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	−0.00193 (9)	0.35588 (7)	0.60358 (8)	0.0457 (3)
O2	0.50090 (9)	0.46871 (7)	0.23813 (9)	0.0510 (3)
O3	0.05797 (8)	0.31431 (6)	0.32341 (8)	0.0414 (2)
O4	0.36378 (8)	0.01835 (6)	0.57454 (9)	0.0410 (2)
C1	0.15314 (11)	0.39480 (8)	0.47929 (11)	0.0327 (3)
C2	0.08369 (12)	0.41451 (9)	0.57557 (11)	0.0367 (3)
C3	0.10230 (13)	0.49068 (9)	0.63775 (12)	0.0420 (3)
H3	0.0522	0.5049	0.7018	0.050*
C4	0.19275 (13)	0.54391 (9)	0.60541 (12)	0.0424 (3)
H4	0.2050	0.5951	0.6481	0.051*
C5	0.36492 (13)	0.57900 (8)	0.47775 (12)	0.0420 (3)
H5	0.3788	0.6301	0.5202	0.050*
C6	0.43770 (13)	0.55914 (9)	0.38729 (12)	0.0423 (3)
H6	0.5013	0.5963	0.3663	0.051*
C7	0.41872 (12)	0.48276 (9)	0.32399 (11)	0.0390 (3)
C8	0.32550 (11)	0.42964 (8)	0.35051 (11)	0.0349 (3)
H8	0.3124	0.3795	0.3056	0.042*
C9	0.24795 (11)	0.44941 (8)	0.44540 (11)	0.0328 (3)
C10	0.26844 (12)	0.52532 (8)	0.51068 (11)	0.0370 (3)
C11	0.12728 (10)	0.31434 (8)	0.41154 (10)	0.0316 (3)
C12	0.18985 (10)	0.23641 (8)	0.45420 (10)	0.0310 (3)
C13	0.16678 (11)	0.16053 (8)	0.39508 (11)	0.0334 (3)
H13	0.1120	0.1596	0.3271	0.040*
C14	0.22189 (11)	0.08668 (8)	0.43339 (11)	0.0347 (3)
H14	0.2046	0.0352	0.3929	0.042*
C15	0.30315 (11)	0.08859 (8)	0.53203 (11)	0.0325 (3)
C16	0.32949 (11)	0.16352 (8)	0.59129 (11)	0.0362 (3)
H16	0.3861	0.1644	0.6578	0.043*
C17	0.27248 (11)	0.23676 (8)	0.55257 (11)	0.0348 (3)
H17	0.2897	0.2881	0.5934	0.042*
C18	−0.06764 (14)	0.36858 (11)	0.70934 (13)	0.0530 (4)
H18A	−0.0098	0.3730	0.7782	0.064*
H18B	−0.1227	0.3209	0.7207	0.064*
H18C	−0.1155	0.4206	0.7017	0.064*
C19	0.49557 (15)	0.38973 (12)	0.17944 (16)	0.0648 (5)
H19A	0.4162	0.3837	0.1365	0.078*
H19B	0.5058	0.3445	0.2385	0.078*
H19C	0.5610	0.3864	0.1227	0.078*
C20	0.31156 (11)	−0.06082 (8)	0.55142 (12)	0.0349 (3)
C21	0.22069 (12)	−0.08914 (9)	0.62315 (12)	0.0403 (3)
H21	0.1893	−0.0538	0.6829	0.048*
C22	0.17631 (12)	−0.17021 (9)	0.60612 (13)	0.0439 (3)
H22	0.1143	−0.1909	0.6550	0.053*
C23	0.22158 (13)	−0.22106 (9)	0.51863 (13)	0.0450 (3)
H23	0.1908	−0.2765	0.5075	0.054*
C24	0.31210 (13)	−0.19118 (9)	0.44695 (13)	0.0446 (3)
H24	0.3430	−0.2262	0.3865	0.054*
C25	0.35762 (12)	−0.11038 (9)	0.46320 (12)	0.0401 (3)
H25	0.4196	−0.0895	0.4143	0.048*

	U11	U22	U33	U12	U13	U23
O1	0.0440 (5)	0.0554 (6)	0.0386 (5)	−0.0030 (4)	0.0117 (4)	−0.0039 (4)
O2	0.0424 (5)	0.0667 (7)	0.0443 (6)	−0.0153 (5)	0.0065 (4)	−0.0021 (5)
O3	0.0440 (5)	0.0426 (5)	0.0365 (5)	0.0021 (4)	−0.0089 (4)	−0.0001 (4)
O4	0.0368 (5)	0.0320 (5)	0.0531 (6)	−0.0008 (4)	−0.0097 (4)	0.0021 (4)
C1	0.0341 (6)	0.0335 (7)	0.0302 (6)	0.0057 (5)	−0.0018 (5)	0.0010 (5)
C2	0.0363 (7)	0.0410 (7)	0.0325 (6)	0.0064 (5)	−0.0005 (5)	0.0016 (5)
C3	0.0489 (8)	0.0453 (8)	0.0316 (6)	0.0131 (6)	−0.0001 (6)	−0.0042 (6)
C4	0.0566 (8)	0.0342 (7)	0.0358 (7)	0.0092 (6)	−0.0061 (6)	−0.0048 (5)
C5	0.0509 (8)	0.0297 (7)	0.0441 (7)	0.0006 (6)	−0.0138 (6)	0.0030 (5)
C6	0.0433 (7)	0.0391 (8)	0.0437 (7)	−0.0077 (6)	−0.0100 (6)	0.0103 (6)
C7	0.0361 (7)	0.0468 (8)	0.0336 (6)	−0.0027 (6)	−0.0042 (5)	0.0061 (6)
C8	0.0359 (7)	0.0361 (7)	0.0325 (6)	−0.0006 (5)	−0.0030 (5)	−0.0005 (5)
C9	0.0358 (6)	0.0312 (7)	0.0310 (6)	0.0038 (5)	−0.0049 (5)	0.0026 (5)
C10	0.0445 (7)	0.0307 (7)	0.0349 (6)	0.0066 (5)	−0.0088 (5)	0.0022 (5)
C11	0.0284 (6)	0.0376 (7)	0.0289 (6)	−0.0008 (5)	0.0037 (5)	0.0011 (5)
C12	0.0292 (6)	0.0343 (7)	0.0297 (6)	−0.0016 (5)	0.0030 (5)	−0.0003 (5)
C13	0.0329 (6)	0.0375 (7)	0.0297 (6)	−0.0020 (5)	−0.0013 (5)	−0.0011 (5)
C14	0.0364 (6)	0.0319 (7)	0.0358 (6)	−0.0030 (5)	−0.0002 (5)	−0.0039 (5)
C15	0.0286 (6)	0.0323 (7)	0.0368 (6)	−0.0007 (5)	0.0031 (5)	0.0028 (5)
C16	0.0335 (6)	0.0385 (7)	0.0362 (7)	−0.0009 (5)	−0.0053 (5)	−0.0007 (5)
C17	0.0351 (6)	0.0335 (7)	0.0356 (6)	−0.0022 (5)	−0.0021 (5)	−0.0037 (5)
C18	0.0490 (8)	0.0731 (11)	0.0377 (7)	0.0016 (8)	0.0115 (6)	0.0004 (7)
C19	0.0486 (9)	0.0861 (13)	0.0613 (10)	−0.0172 (9)	0.0207 (8)	−0.0246 (9)
C20	0.0301 (6)	0.0314 (7)	0.0426 (7)	0.0011 (5)	−0.0044 (5)	0.0034 (5)
C21	0.0354 (7)	0.0437 (8)	0.0420 (7)	0.0032 (6)	0.0022 (5)	−0.0008 (6)
C22	0.0355 (7)	0.0472 (8)	0.0492 (8)	−0.0043 (6)	0.0027 (6)	0.0101 (6)
C23	0.0440 (8)	0.0323 (7)	0.0581 (9)	−0.0008 (6)	−0.0056 (6)	0.0057 (6)
C24	0.0469 (8)	0.0363 (8)	0.0508 (8)	0.0072 (6)	0.0035 (6)	−0.0032 (6)
C25	0.0355 (7)	0.0395 (8)	0.0458 (7)	0.0028 (6)	0.0060 (6)	0.0047 (6)

O1—C2	1.3677 (16)	C12—C17	1.3969 (17)
O1—C18	1.4282 (16)	C13—C14	1.3794 (18)
O2—C7	1.3645 (16)	C13—H13	0.9500
O2—C19	1.417 (2)	C14—C15	1.3903 (17)
O3—C11	1.2203 (15)	C14—H14	0.9500
O4—C15	1.3732 (15)	C15—C16	1.3875 (18)
O4—C20	1.4011 (15)	C16—C17	1.3814 (18)
C1—C2	1.3833 (17)	C16—H16	0.9500
C1—C9	1.4174 (18)	C17—H17	0.9500
C1—C11	1.5074 (17)	C18—H18A	0.9800
C2—C3	1.4070 (19)	C18—H18B	0.9800
C3—C4	1.363 (2)	C18—H18C	0.9800
C3—H3	0.9500	C19—H19A	0.9800
C4—C10	1.4068 (19)	C19—H19B	0.9800
C4—H4	0.9500	C19—H19C	0.9800
C5—C6	1.354 (2)	C20—C25	1.3771 (19)
C5—C10	1.419 (2)	C20—C21	1.3816 (18)
C5—H5	0.9500	C21—C22	1.387 (2)
C6—C7	1.416 (2)	C21—H21	0.9500
C6—H6	0.9500	C22—C23	1.380 (2)
C7—C8	1.3670 (18)	C22—H22	0.9500
C8—C9	1.4250 (18)	C23—C24	1.387 (2)
C8—H8	0.9500	C23—H23	0.9500
C9—C10	1.4234 (18)	C24—C25	1.386 (2)
C11—C12	1.4841 (17)	C24—H24	0.9500
C12—C13	1.3935 (17)	C25—H25	0.9500
C2—O1—C18	118.00 (11)	C13—C14—C15	119.08 (11)
C7—O2—C19	117.23 (11)	C13—C14—H14	120.5
C15—O4—C20	118.52 (9)	C15—C14—H14	120.5
C2—C1—C9	120.30 (12)	O4—C15—C16	116.29 (11)
C2—C1—C11	119.20 (11)	O4—C15—C14	122.83 (11)
C9—C1—C11	120.50 (11)	C16—C15—C14	120.86 (11)
O1—C2—C1	115.50 (12)	C17—C16—C15	119.33 (11)
O1—C2—C3	123.90 (12)	C17—C16—H16	120.3
C1—C2—C3	120.60 (13)	C15—C16—H16	120.3
C4—C3—C2	119.52 (12)	C16—C17—C12	120.91 (12)
C4—C3—H3	120.2	C16—C17—H17	119.5
C2—C3—H3	120.2	C12—C17—H17	119.5
C3—C4—C10	121.96 (13)	O1—C18—H18A	109.5
C3—C4—H4	119.0	O1—C18—H18B	109.5
C10—C4—H4	119.0	H18A—C18—H18B	109.5
C6—C5—C10	121.60 (13)	O1—C18—H18C	109.5
C6—C5—H5	119.2	H18A—C18—H18C	109.5
C10—C5—H5	119.2	H18B—C18—H18C	109.5
C5—C6—C7	119.78 (13)	O2—C19—H19A	109.5
C5—C6—H6	120.1	O2—C19—H19B	109.5
C7—C6—H6	120.1	H19A—C19—H19B	109.5
O2—C7—C8	125.03 (13)	O2—C19—H19C	109.5
O2—C7—C6	114.01 (12)	H19A—C19—H19C	109.5
C8—C7—C6	120.96 (13)	H19B—C19—H19C	109.5
C7—C8—C9	120.07 (12)	C25—C20—C21	121.85 (13)
C7—C8—H8	120.0	C25—C20—O4	119.14 (12)
C9—C8—H8	120.0	C21—C20—O4	118.87 (12)
C1—C9—C10	118.78 (12)	C20—C21—C22	118.62 (13)
C1—C9—C8	122.17 (11)	C20—C21—H21	120.7
C10—C9—C8	119.02 (12)	C22—C21—H21	120.7
C4—C10—C5	122.68 (13)	C23—C22—C21	120.48 (13)
C4—C10—C9	118.78 (13)	C23—C22—H22	119.8
C5—C10—C9	118.53 (12)	C21—C22—H22	119.8
O3—C11—C12	121.56 (11)	C22—C23—C24	119.99 (13)
O3—C11—C1	120.38 (11)	C22—C23—H23	120.0
C12—C11—C1	118.05 (10)	C24—C23—H23	120.0
C13—C12—C17	118.53 (11)	C25—C24—C23	120.17 (13)
C13—C12—C11	119.74 (11)	C25—C24—H24	119.9
C17—C12—C11	121.73 (11)	C23—C24—H24	119.9
C14—C13—C12	121.28 (11)	C20—C25—C24	118.88 (13)
C14—C13—H13	119.4	C20—C25—H25	120.6
C12—C13—H13	119.4	C24—C25—H25	120.6
C18—O1—C2—C1	173.66 (12)	C2—C1—C11—O3	93.21 (15)
C18—O1—C2—C3	−6.68 (19)	C9—C1—C11—O3	−87.20 (15)
C9—C1—C2—O1	−177.41 (10)	C2—C1—C11—C12	−87.71 (14)
C11—C1—C2—O1	2.18 (17)	C9—C1—C11—C12	91.87 (13)
C9—C1—C2—C3	2.93 (18)	O3—C11—C12—C13	−1.97 (18)
C11—C1—C2—C3	−177.49 (11)	C1—C11—C12—C13	178.96 (11)
O1—C2—C3—C4	177.88 (12)	O3—C11—C12—C17	177.75 (11)
C1—C2—C3—C4	−2.48 (19)	C1—C11—C12—C17	−1.31 (17)
C2—C3—C4—C10	0.3 (2)	C17—C12—C13—C14	1.26 (18)
C10—C5—C6—C7	−0.58 (19)	C11—C12—C13—C14	−179.00 (11)
C19—O2—C7—C8	−5.8 (2)	C12—C13—C14—C15	−0.83 (18)
C19—O2—C7—C6	173.69 (13)	C20—O4—C15—C16	156.41 (11)
C5—C6—C7—O2	−177.64 (12)	C20—O4—C15—C14	−25.21 (17)
C5—C6—C7—C8	1.92 (19)	C13—C14—C15—O4	−178.65 (11)
O2—C7—C8—C9	177.58 (11)	C13—C14—C15—C16	−0.34 (18)
C6—C7—C8—C9	−1.93 (19)	O4—C15—C16—C17	179.47 (11)
C2—C1—C9—C10	−1.23 (17)	C14—C15—C16—C17	1.05 (19)
C11—C1—C9—C10	179.19 (10)	C15—C16—C17—C12	−0.60 (19)
C2—C1—C9—C8	176.92 (11)	C13—C12—C17—C16	−0.53 (18)
C11—C1—C9—C8	−2.66 (17)	C11—C12—C17—C16	179.74 (11)
C7—C8—C9—C1	−177.51 (11)	C15—O4—C20—C25	102.71 (14)
C7—C8—C9—C10	0.64 (18)	C15—O4—C20—C21	−81.52 (15)
C3—C4—C10—C5	−178.39 (12)	C25—C20—C21—C22	0.82 (19)
C3—C4—C10—C9	1.32 (19)	O4—C20—C21—C22	−174.82 (11)
C6—C5—C10—C4	179.03 (12)	C20—C21—C22—C23	−0.5 (2)
C6—C5—C10—C9	−0.67 (18)	C21—C22—C23—C24	0.0 (2)
C1—C9—C10—C4	−0.86 (17)	C22—C23—C24—C25	0.2 (2)
C8—C9—C10—C4	−179.07 (11)	C21—C20—C25—C24	−0.6 (2)
C1—C9—C10—C5	178.86 (11)	O4—C20—C25—C24	175.01 (11)
C8—C9—C10—C5	0.65 (17)	C23—C24—C25—C20	0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O2i	0.95	2.56	3.3738 (17)	143
C19—H19A···Cg1ii	0.98	2.74	3.6967 (18)	164
C19—H19C···Cg2iii	0.98	2.67	3.6249 (18)	165

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C20–C25 and C12–C17 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯O2i	0.95	2.56	3.3738 (17)	143
C19—H19A⋯Cg1ii	0.98	2.74	3.6967 (18)	164
C19—H19C⋯Cg2iii	0.98	2.67	3.6249 (18)	165

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