(2,7-Dimeth-oxy-naphthalen-1-yl)(2,4,6-trimethyl-phen-yl)methanone.

In the title compound, C(22)H(22)O(3), the dihedral angle between the naphthalene ring system and the benzene ring is 82.93 (5)°. The bridging carbonyl C-C(=O)-C plane makes dihedral angles of 50.11 (6) and 46.87 (7)°, respectively, with the naphthalene ring system and the benzene ring. In the crystal, three types of weak inter-molecular C-H⋯O inter-actions are observed.

Related literature

For electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009 ▶); Okamoto et al. (2011 ▶). For the structures of closely related compounds, see: Muto et al. (2010 ▶); Watanabe et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C22H22O3

M = 334.40

Monoclinic,

a = 10.5238 (4) Å

b = 12.2289 (4) Å

c = 15.0504 (5) Å

β = 111.340 (2)°

V = 1804.11 (11) Å3

Z = 4

Cu Kα radiation

μ = 0.64 mm−1

T = 193 K

0.50 × 0.40 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.739, T max = 0.882

32585 measured reflections

3295 independent reflections

2945 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.112

S = 1.08

3295 reflections

232 parameters

H-atom parameters constrained

Δρmax = 0.26 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 datablock(s) I, global. DOI: 10.1107/S1600536811039225/zk2031sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039225/zk2031Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039225/zk2031Isup3.cml

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

C22H22O3	F(000) = 712
Mr = 334.40	Dx = 1.231 Mg m−3
Monoclinic, P21/c	Melting point = 408.0–410.0 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54187 Å
a = 10.5238 (4) Å	Cell parameters from 15327 reflections
b = 12.2289 (4) Å	θ = 3.2–68.1°
c = 15.0504 (5) Å	µ = 0.64 mm−1
β = 111.340 (2)°	T = 193 K
V = 1804.11 (11) Å3	Block, colorless
Z = 4	0.50 × 0.40 × 0.20 mm

Rigaku R-AXIS RAPID diffractometer	3295 independent reflections
Radiation source: rotating anode	2945 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 10.000 pixels mm-1	θmax = 68.2°, θmin = 4.5°
ω scans	h = −12→12
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −14→14
Tmin = 0.739, Tmax = 0.882	l = −18→18
32585 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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0568P)2 + 0.4166P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
3295 reflections	Δρmax = 0.26 e Å−3
232 parameters	Δρmin = −0.25 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: 0.0080 (5)

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	0.37023 (10)	0.11774 (8)	0.92101 (7)	0.0486 (3)
O2	0.12893 (10)	0.13899 (8)	0.66767 (6)	0.0484 (3)
O3	0.68551 (11)	0.43082 (10)	1.02164 (8)	0.0629 (3)
C1	0.30975 (12)	0.22890 (10)	0.78444 (9)	0.0358 (3)
C2	0.23219 (13)	0.21417 (11)	0.68881 (9)	0.0400 (3)
C3	0.26304 (15)	0.27038 (12)	0.61732 (10)	0.0481 (4)
H3	0.2094	0.2590	0.5519	0.058*
C4	0.37039 (16)	0.34113 (12)	0.64283 (10)	0.0497 (4)
H4	0.3916	0.3780	0.5944	0.060*
C5	0.45068 (14)	0.36101 (11)	0.73909 (10)	0.0438 (3)
C6	0.55965 (15)	0.43751 (12)	0.76592 (12)	0.0539 (4)
H6	0.5804	0.4755	0.7178	0.065*
C7	0.63442 (15)	0.45735 (13)	0.85870 (13)	0.0565 (4)
H7	0.7077	0.5081	0.8752	0.068*
C8	0.60373 (14)	0.40273 (12)	0.93107 (11)	0.0487 (3)
C9	0.50014 (13)	0.32777 (11)	0.90886 (9)	0.0415 (3)
H9	0.4809	0.2915	0.9584	0.050*
C10	0.42134 (12)	0.30417 (10)	0.81193 (9)	0.0379 (3)
C11	0.27808 (13)	0.16488 (10)	0.85879 (8)	0.0358 (3)
C12	0.13503 (13)	0.15946 (10)	0.85716 (8)	0.0353 (3)
C13	0.05612 (13)	0.25478 (10)	0.84617 (9)	0.0385 (3)
C14	−0.07551 (14)	0.24589 (11)	0.84654 (9)	0.0437 (3)
H14	−0.1292	0.3102	0.8389	0.052*
C15	−0.13086 (14)	0.14637 (12)	0.85775 (10)	0.0458 (3)
C16	−0.05042 (14)	0.05397 (11)	0.87003 (10)	0.0462 (3)
H16	−0.0867	−0.0146	0.8788	0.055*
C17	0.08180 (14)	0.05783 (10)	0.86999 (9)	0.0406 (3)
C18	0.02367 (17)	0.14400 (14)	0.57628 (12)	0.0638 (4)
H18A	−0.0067	0.2199	0.5618	0.077*
H18B	−0.0533	0.0986	0.5759	0.077*
H18C	0.0583	0.1170	0.5281	0.077*
C19	0.66243 (19)	0.37810 (16)	1.09841 (13)	0.0703 (5)
H19A	0.6729	0.2989	1.0937	0.084*
H19B	0.5698	0.3944	1.0955	0.084*
H19C	0.7287	0.4046	1.1590	0.084*
C20	0.11031 (16)	0.36753 (11)	0.83889 (12)	0.0504 (4)
H20A	0.1250	0.3741	0.7784	0.061*
H20B	0.1969	0.3789	0.8921	0.061*
H20C	0.0441	0.4227	0.8414	0.061*
C21	−0.27449 (16)	0.14021 (15)	0.85686 (14)	0.0639 (5)
H21A	−0.2992	0.0636	0.8606	0.077*
H21B	−0.3376	0.1726	0.7977	0.077*
H21C	−0.2800	0.1805	0.9117	0.077*
C22	0.16095 (16)	−0.04745 (12)	0.87986 (13)	0.0569 (4)
H22A	0.2396	−0.0467	0.9401	0.068*
H22B	0.1927	−0.0544	0.8265	0.068*
H22C	0.1018	−0.1095	0.8795	0.068*

	U11	U22	U33	U12	U13	U23
O1	0.0445 (5)	0.0555 (6)	0.0429 (5)	0.0012 (4)	0.0126 (4)	0.0122 (4)
O2	0.0554 (6)	0.0534 (6)	0.0327 (5)	−0.0105 (4)	0.0115 (4)	−0.0034 (4)
O3	0.0491 (6)	0.0660 (7)	0.0622 (7)	−0.0138 (5)	0.0066 (5)	−0.0090 (5)
C1	0.0394 (6)	0.0382 (6)	0.0329 (6)	0.0018 (5)	0.0168 (5)	0.0003 (5)
C2	0.0472 (7)	0.0402 (7)	0.0346 (7)	0.0016 (5)	0.0175 (6)	−0.0010 (5)
C3	0.0649 (9)	0.0500 (8)	0.0325 (7)	0.0041 (7)	0.0213 (6)	0.0012 (6)
C4	0.0663 (9)	0.0480 (8)	0.0462 (8)	0.0050 (7)	0.0341 (7)	0.0081 (6)
C5	0.0460 (7)	0.0439 (7)	0.0491 (8)	0.0041 (6)	0.0262 (6)	0.0052 (6)
C6	0.0526 (8)	0.0497 (8)	0.0706 (10)	−0.0007 (6)	0.0359 (8)	0.0089 (7)
C7	0.0431 (8)	0.0493 (8)	0.0803 (11)	−0.0071 (6)	0.0261 (8)	0.0016 (8)
C8	0.0373 (7)	0.0473 (8)	0.0586 (9)	0.0000 (6)	0.0139 (6)	−0.0044 (6)
C9	0.0379 (7)	0.0440 (7)	0.0437 (7)	0.0003 (5)	0.0162 (6)	−0.0008 (6)
C10	0.0378 (6)	0.0386 (7)	0.0414 (7)	0.0038 (5)	0.0192 (5)	0.0010 (5)
C11	0.0418 (7)	0.0358 (6)	0.0290 (6)	−0.0019 (5)	0.0121 (5)	−0.0027 (5)
C12	0.0415 (7)	0.0390 (6)	0.0263 (6)	−0.0027 (5)	0.0135 (5)	−0.0024 (5)
C13	0.0460 (7)	0.0379 (6)	0.0329 (6)	−0.0023 (5)	0.0158 (5)	−0.0040 (5)
C14	0.0467 (7)	0.0437 (7)	0.0431 (7)	0.0019 (6)	0.0192 (6)	−0.0054 (6)
C15	0.0452 (7)	0.0524 (8)	0.0439 (7)	−0.0053 (6)	0.0209 (6)	−0.0090 (6)
C16	0.0525 (8)	0.0431 (7)	0.0477 (8)	−0.0099 (6)	0.0237 (6)	−0.0031 (6)
C17	0.0471 (7)	0.0386 (7)	0.0374 (7)	−0.0031 (5)	0.0170 (6)	−0.0002 (5)
C18	0.0582 (9)	0.0627 (10)	0.0544 (10)	−0.0011 (8)	0.0014 (8)	0.0022 (7)
C19	0.0629 (10)	0.0782 (12)	0.0547 (10)	−0.0117 (9)	0.0035 (8)	−0.0099 (9)
C20	0.0562 (8)	0.0371 (7)	0.0630 (9)	0.0008 (6)	0.0276 (7)	−0.0007 (6)
C21	0.0526 (9)	0.0698 (10)	0.0793 (12)	−0.0065 (8)	0.0358 (9)	−0.0094 (9)
C22	0.0570 (9)	0.0386 (7)	0.0753 (11)	−0.0005 (6)	0.0243 (8)	0.0049 (7)

O1—C11	1.2201 (15)	C13—C14	1.3916 (19)
O2—C2	1.3696 (16)	C13—C20	1.5112 (18)
O2—C18	1.4190 (18)	C14—C15	1.3858 (19)
O3—C8	1.3650 (18)	C14—H14	0.9500
O3—C19	1.419 (2)	C15—C16	1.383 (2)
C1—C2	1.3840 (18)	C15—C21	1.5087 (19)
C1—C10	1.4296 (18)	C16—C17	1.3924 (19)
C1—C11	1.4991 (16)	C16—H16	0.9500
C2—C3	1.4105 (18)	C17—C22	1.5111 (19)
C3—C4	1.363 (2)	C18—H18A	0.9800
C3—H3	0.9500	C18—H18B	0.9800
C4—C5	1.407 (2)	C18—H18C	0.9800
C4—H4	0.9500	C19—H19A	0.9800
C5—C6	1.420 (2)	C19—H19B	0.9800
C5—C10	1.4236 (18)	C19—H19C	0.9800
C6—C7	1.352 (2)	C20—H20A	0.9800
C6—H6	0.9500	C20—H20B	0.9800
C7—C8	1.412 (2)	C20—H20C	0.9800
C7—H7	0.9500	C21—H21A	0.9800
C8—C9	1.3694 (19)	C21—H21B	0.9800
C9—C10	1.4208 (18)	C21—H21C	0.9800
C9—H9	0.9500	C22—H22A	0.9800
C11—C12	1.4982 (17)	C22—H22B	0.9800
C12—C17	1.4051 (17)	C22—H22C	0.9800
C12—C13	1.4056 (18)
C2—O2—C18	118.01 (11)	C15—C14—H14	118.9
C8—O3—C19	117.79 (12)	C13—C14—H14	118.9
C2—C1—C10	119.75 (11)	C16—C15—C14	118.02 (12)
C2—C1—C11	120.07 (11)	C16—C15—C21	121.52 (13)
C10—C1—C11	120.17 (11)	C14—C15—C21	120.46 (13)
O2—C2—C1	116.54 (11)	C15—C16—C17	122.36 (12)
O2—C2—C3	122.23 (12)	C15—C16—H16	118.8
C1—C2—C3	121.16 (12)	C17—C16—H16	118.8
C4—C3—C2	119.46 (13)	C16—C17—C12	118.59 (12)
C4—C3—H3	120.3	C16—C17—C22	119.09 (12)
C2—C3—H3	120.3	C12—C17—C22	122.28 (12)
C3—C4—C5	121.69 (12)	O2—C18—H18A	109.5
C3—C4—H4	119.2	O2—C18—H18B	109.5
C5—C4—H4	119.2	H18A—C18—H18B	109.5
C4—C5—C6	121.78 (13)	O2—C18—H18C	109.5
C4—C5—C10	119.41 (13)	H18A—C18—H18C	109.5
C6—C5—C10	118.80 (13)	H18B—C18—H18C	109.5
C7—C6—C5	121.20 (13)	O3—C19—H19A	109.5
C7—C6—H6	119.4	O3—C19—H19B	109.5
C5—C6—H6	119.4	H19A—C19—H19B	109.5
C6—C7—C8	120.10 (14)	O3—C19—H19C	109.5
C6—C7—H7	120.0	H19A—C19—H19C	109.5
C8—C7—H7	120.0	H19B—C19—H19C	109.5
O3—C8—C9	124.67 (14)	C13—C20—H20A	109.5
O3—C8—C7	114.41 (13)	C13—C20—H20B	109.5
C9—C8—C7	120.91 (14)	H20A—C20—H20B	109.5
C8—C9—C10	120.13 (13)	C13—C20—H20C	109.5
C8—C9—H9	119.9	H20A—C20—H20C	109.5
C10—C9—H9	119.9	H20B—C20—H20C	109.5
C9—C10—C5	118.84 (12)	C15—C21—H21A	109.5
C9—C10—C1	122.61 (11)	C15—C21—H21B	109.5
C5—C10—C1	118.49 (12)	H21A—C21—H21B	109.5
O1—C11—C12	120.33 (11)	C15—C21—H21C	109.5
O1—C11—C1	119.28 (11)	H21A—C21—H21C	109.5
C12—C11—C1	120.39 (10)	H21B—C21—H21C	109.5
C17—C12—C13	120.11 (12)	C17—C22—H22A	109.5
C17—C12—C11	119.04 (11)	C17—C22—H22B	109.5
C13—C12—C11	120.82 (11)	H22A—C22—H22B	109.5
C14—C13—C12	118.76 (12)	C17—C22—H22C	109.5
C14—C13—C20	118.30 (12)	H22A—C22—H22C	109.5
C12—C13—C20	122.87 (12)	H22B—C22—H22C	109.5
C15—C14—C13	122.15 (12)
C18—O2—C2—C1	161.62 (13)	C11—C1—C10—C9	−4.59 (18)
C18—O2—C2—C3	−21.32 (19)	C2—C1—C10—C5	−0.93 (18)
C10—C1—C2—O2	178.56 (11)	C11—C1—C10—C5	178.15 (11)
C11—C1—C2—O2	−0.52 (17)	C2—C1—C11—O1	130.97 (13)
C10—C1—C2—C3	1.46 (19)	C10—C1—C11—O1	−48.11 (17)
C11—C1—C2—C3	−177.62 (12)	C2—C1—C11—C12	−49.47 (16)
O2—C2—C3—C4	−177.48 (12)	C10—C1—C11—C12	131.46 (12)
C1—C2—C3—C4	−0.5 (2)	O1—C11—C12—C17	−46.12 (17)
C2—C3—C4—C5	−0.9 (2)	C1—C11—C12—C17	134.33 (12)
C3—C4—C5—C6	−177.78 (14)	O1—C11—C12—C13	131.78 (13)
C3—C4—C5—C10	1.4 (2)	C1—C11—C12—C13	−47.77 (16)
C4—C5—C6—C7	178.76 (14)	C17—C12—C13—C14	−1.15 (18)
C10—C5—C6—C7	−0.4 (2)	C11—C12—C13—C14	−179.03 (11)
C5—C6—C7—C8	−0.8 (2)	C17—C12—C13—C20	175.68 (12)
C19—O3—C8—C9	0.5 (2)	C11—C12—C13—C20	−2.20 (18)
C19—O3—C8—C7	−179.03 (14)	C12—C13—C14—C15	0.25 (19)
C6—C7—C8—O3	−179.25 (14)	C20—C13—C14—C15	−176.73 (13)
C6—C7—C8—C9	1.2 (2)	C13—C14—C15—C16	0.8 (2)
O3—C8—C9—C10	−179.74 (12)	C13—C14—C15—C21	−179.45 (13)
C7—C8—C9—C10	−0.2 (2)	C14—C15—C16—C17	−1.0 (2)
C8—C9—C10—C5	−1.05 (19)	C21—C15—C16—C17	179.27 (13)
C8—C9—C10—C1	−178.31 (12)	C15—C16—C17—C12	0.1 (2)
C4—C5—C10—C9	−177.84 (12)	C15—C16—C17—C22	−177.54 (13)
C6—C5—C10—C9	1.38 (19)	C13—C12—C17—C16	0.97 (18)
C4—C5—C10—C1	−0.47 (18)	C11—C12—C17—C16	178.89 (11)
C6—C5—C10—C1	178.75 (12)	C13—C12—C17—C22	178.55 (12)
C2—C1—C10—C9	176.34 (11)	C11—C12—C17—C22	−3.53 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1i	0.95	2.54	3.3756 (18)	147
C7—H7···O2ii	0.95	2.60	3.466 (2)	152
C9—H9···O1	0.95	2.39	2.9464 (17)	117
C18—H18B···O3iii	0.98	2.59	3.471 (2)	149
C22—H22A···O1	0.98	2.51	2.885 (2)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1i	0.95	2.54	3.3756 (18)	147
C7—H7⋯O2ii	0.95	2.60	3.466 (2)	152
C18—H18B⋯O3iii	0.98	2.59	3.471 (2)	149

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