(3,6-Dimeth-oxy-naphthalen-2-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 79.95 (5)°. The bridging carbonyl C-C(=O)-C group makes dihedral angles of 24.21 (7) and 82.43 (8)°, respectively, with the naphthalene ring system and the benzene ring. In the crystal, weak inter-molecular C-H⋯O inter-actions link mol-ecules into chains parallel to the c axis.

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 ▶, 2011 ▶); Kato et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C22H22O3

M = 334.40

Monoclinic,

a = 15.4205 (2) Å

b = 8.23702 (10) Å

c = 15.3832 (2) Å

β = 111.30 (1)°

V = 1820.49 (13) Å3

Z = 4

Cu Kα radiation

μ = 0.64 mm−1

T = 193 K

0.60 × 0.20 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi 1999 ▶) T min = 0.701, T max = 0.939

32532 measured reflections

3310 independent reflections

3047 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.130

S = 1.04

3310 reflections

232 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.21 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/S1600536811042401/rz2647sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042401/rz2647Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042401/rz2647Isup3.cml

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

C22H22O3	F(000) = 712
Mr = 334.40	Dx = 1.220 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ybc	Cell parameters from 29183 reflections
a = 15.4205 (2) Å	θ = 3.1–68.3°
b = 8.23702 (10) Å	µ = 0.64 mm−1
c = 15.3832 (2) Å	T = 193 K
β = 111.30 (1)°	Platelet, colourless
V = 1820.49 (13) Å3	0.60 × 0.20 × 0.10 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	3310 independent reflections
Radiation source: rotating anode	3047 reflections with I > 2σ(I)
graphite	Rint = 0.035
Detector resolution: 10.000 pixels mm-1	θmax = 68.2°, θmin = 3.1°
ω scans	h = −18→18
Absorption correction: numerical (NUMABS; Higashi 1999)	k = −9→9
Tmin = 0.701, Tmax = 0.939	l = −18→18
32532 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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.0753P)2 + 0.4568P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3310 reflections	Δρmax = 0.24 e Å−3
232 parameters	Δρmin = −0.21 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: 0.0049 (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	0.17897 (7)	0.11520 (14)	0.30253 (7)	0.0547 (3)
O2	0.31350 (9)	−0.09944 (15)	0.39268 (8)	0.0644 (4)
O3	0.51070 (7)	0.05027 (14)	0.89570 (7)	0.0524 (3)
C1	0.38282 (10)	−0.06216 (18)	0.55932 (10)	0.0469 (4)
H1	0.4328	−0.1328	0.5633	0.056*
C2	0.31489 (10)	−0.03276 (18)	0.47401 (10)	0.0463 (3)
C3	0.23765 (9)	0.07077 (17)	0.46641 (9)	0.0407 (3)
C4	0.23345 (9)	0.13606 (16)	0.54713 (9)	0.0399 (3)
H4	0.1812	0.2009	0.5431	0.048*
C5	0.30303 (9)	0.11102 (16)	0.63517 (10)	0.0397 (3)
C6	0.29974 (9)	0.18543 (18)	0.71684 (10)	0.0443 (3)
H6	0.2481	0.2519	0.7130	0.053*
C7	0.36953 (9)	0.16311 (18)	0.80084 (10)	0.0456 (3)
H7	0.3667	0.2145	0.8550	0.055*
C8	0.44640 (9)	0.06316 (17)	0.80730 (10)	0.0424 (3)
C9	0.45182 (9)	−0.01199 (17)	0.73013 (10)	0.0433 (3)
H9	0.5036	−0.0793	0.7357	0.052*
C10	0.38003 (9)	0.01067 (16)	0.64181 (10)	0.0406 (3)
C11	0.16556 (9)	0.11889 (16)	0.37545 (9)	0.0407 (3)
C12	0.07397 (9)	0.18112 (16)	0.37644 (8)	0.0380 (3)
C13	0.00479 (9)	0.07062 (17)	0.37435 (9)	0.0420 (3)
C14	−0.08108 (10)	0.1316 (2)	0.37005 (10)	0.0475 (4)
H14	−0.1293	0.0576	0.3672	0.057*
C15	−0.09821 (10)	0.2967 (2)	0.36976 (10)	0.0500 (4)
C16	−0.02745 (11)	0.40317 (18)	0.37347 (10)	0.0503 (4)
H16	−0.0381	0.5166	0.3743	0.060*
C17	0.05866 (10)	0.34880 (17)	0.37602 (9)	0.0435 (3)
C18	0.38758 (15)	−0.2040 (3)	0.39608 (14)	0.0781 (6)
H18A	0.3878	−0.2989	0.4346	0.094*
H18B	0.4468	−0.1460	0.4232	0.094*
H18C	0.3793	−0.2396	0.3328	0.094*
C19	0.58995 (11)	−0.0495 (2)	0.90841 (12)	0.0635 (5)
H19A	0.6244	−0.0067	0.8710	0.076*
H19B	0.5696	−0.1606	0.8885	0.076*
H19C	0.6304	−0.0496	0.9744	0.076*
C20	0.02088 (11)	−0.10973 (18)	0.37508 (11)	0.0529 (4)
H20A	0.0609	−0.1438	0.4379	0.063*
H20B	0.0511	−0.1362	0.3308	0.063*
H20C	−0.0389	−0.1665	0.3571	0.063*
C21	−0.19204 (12)	0.3592 (3)	0.36448 (14)	0.0696 (5)
H21A	−0.2273	0.2709	0.3788	0.084*
H21B	−0.2263	0.4003	0.3015	0.084*
H21C	−0.1834	0.4472	0.4098	0.084*
C22	0.13333 (12)	0.46853 (19)	0.37718 (12)	0.0572 (4)
H22A	0.1914	0.4422	0.4287	0.069*
H22B	0.1136	0.5786	0.3857	0.069*
H22C	0.1435	0.4624	0.3180	0.069*

	U11	U22	U33	U12	U13	U23
O1	0.0597 (6)	0.0639 (7)	0.0500 (6)	0.0070 (5)	0.0312 (5)	0.0096 (5)
O2	0.0725 (7)	0.0710 (8)	0.0509 (6)	0.0287 (6)	0.0238 (5)	−0.0071 (5)
O3	0.0453 (6)	0.0567 (7)	0.0503 (6)	0.0041 (4)	0.0116 (4)	−0.0015 (5)
C1	0.0439 (7)	0.0456 (8)	0.0553 (8)	0.0112 (6)	0.0228 (6)	−0.0012 (6)
C2	0.0508 (8)	0.0445 (8)	0.0490 (8)	0.0064 (6)	0.0247 (6)	−0.0028 (6)
C3	0.0409 (7)	0.0388 (7)	0.0467 (7)	0.0020 (5)	0.0209 (6)	0.0024 (5)
C4	0.0377 (6)	0.0392 (7)	0.0484 (7)	0.0044 (5)	0.0222 (6)	0.0031 (5)
C5	0.0378 (7)	0.0380 (7)	0.0485 (7)	0.0014 (5)	0.0221 (6)	0.0019 (5)
C6	0.0426 (7)	0.0456 (8)	0.0503 (8)	0.0071 (6)	0.0236 (6)	0.0013 (6)
C7	0.0475 (7)	0.0465 (8)	0.0475 (7)	0.0013 (6)	0.0228 (6)	−0.0019 (6)
C8	0.0385 (7)	0.0409 (7)	0.0475 (7)	−0.0038 (5)	0.0154 (6)	0.0022 (6)
C9	0.0366 (7)	0.0402 (7)	0.0554 (8)	0.0038 (5)	0.0195 (6)	0.0019 (6)
C10	0.0386 (7)	0.0374 (7)	0.0503 (7)	0.0012 (5)	0.0215 (6)	0.0019 (6)
C11	0.0457 (7)	0.0356 (7)	0.0455 (7)	−0.0027 (5)	0.0220 (6)	0.0023 (5)
C12	0.0405 (6)	0.0388 (7)	0.0353 (6)	0.0013 (5)	0.0145 (5)	0.0024 (5)
C13	0.0472 (7)	0.0414 (7)	0.0396 (7)	−0.0021 (6)	0.0185 (6)	0.0016 (5)
C14	0.0426 (7)	0.0572 (9)	0.0459 (7)	−0.0040 (6)	0.0199 (6)	0.0028 (6)
C15	0.0478 (8)	0.0611 (9)	0.0431 (7)	0.0109 (7)	0.0188 (6)	0.0053 (6)
C16	0.0560 (9)	0.0426 (8)	0.0511 (8)	0.0118 (6)	0.0181 (7)	0.0028 (6)
C17	0.0483 (8)	0.0382 (7)	0.0417 (7)	0.0012 (6)	0.0138 (6)	0.0021 (5)
C18	0.0894 (13)	0.0862 (14)	0.0635 (11)	0.0390 (11)	0.0334 (10)	−0.0077 (10)
C19	0.0438 (8)	0.0745 (12)	0.0640 (10)	0.0091 (8)	0.0098 (7)	0.0015 (8)
C20	0.0618 (9)	0.0403 (8)	0.0610 (9)	−0.0061 (7)	0.0276 (8)	0.0017 (7)
C21	0.0572 (10)	0.0882 (13)	0.0698 (11)	0.0210 (9)	0.0307 (8)	0.0101 (10)
C22	0.0605 (9)	0.0403 (8)	0.0660 (10)	−0.0050 (7)	0.0172 (8)	0.0037 (7)

O1—C11	1.2126 (16)	C13—C14	1.395 (2)
O2—C2	1.3595 (17)	C13—C20	1.505 (2)
O2—C18	1.4166 (19)	C14—C15	1.385 (2)
O3—C8	1.3653 (17)	C14—H14	0.9500
O3—C19	1.4258 (19)	C15—C16	1.385 (2)
C1—C2	1.371 (2)	C15—C21	1.510 (2)
C1—C10	1.418 (2)	C16—C17	1.388 (2)
C1—H1	0.9500	C16—H16	0.9500
C2—C3	1.4347 (19)	C17—C22	1.511 (2)
C3—C4	1.3761 (19)	C18—H18A	0.9800
C3—C11	1.4903 (19)	C18—H18B	0.9800
C4—C5	1.404 (2)	C18—H18C	0.9800
C4—H4	0.9500	C19—H19A	0.9800
C5—C6	1.4153 (19)	C19—H19B	0.9800
C5—C10	1.4196 (18)	C19—H19C	0.9800
C6—C7	1.361 (2)	C20—H20A	0.9800
C6—H6	0.9500	C20—H20B	0.9800
C7—C8	1.4167 (19)	C20—H20C	0.9800
C7—H7	0.9500	C21—H21A	0.9800
C8—C9	1.368 (2)	C21—H21B	0.9800
C9—C10	1.419 (2)	C21—H21C	0.9800
C9—H9	0.9500	C22—H22A	0.9800
C11—C12	1.5077 (18)	C22—H22B	0.9800
C12—C13	1.3938 (19)	C22—H22C	0.9800
C12—C17	1.401 (2)
C2—O2—C18	117.96 (13)	C15—C14—H14	119.0
C8—O3—C19	117.24 (12)	C13—C14—H14	119.0
C2—C1—C10	121.38 (12)	C16—C15—C14	118.37 (13)
C2—C1—H1	119.3	C16—C15—C21	120.77 (15)
C10—C1—H1	119.3	C14—C15—C21	120.86 (15)
O2—C2—C1	124.10 (13)	C15—C16—C17	121.88 (14)
O2—C2—C3	115.47 (12)	C15—C16—H16	119.1
C1—C2—C3	120.41 (12)	C17—C16—H16	119.1
C4—C3—C2	117.94 (12)	C16—C17—C12	118.43 (13)
C4—C3—C11	118.67 (12)	C16—C17—C22	120.44 (14)
C2—C3—C11	123.27 (12)	C12—C17—C22	121.13 (13)
C3—C4—C5	122.88 (12)	O2—C18—H18A	109.5
C3—C4—H4	118.6	O2—C18—H18B	109.5
C5—C4—H4	118.6	H18A—C18—H18B	109.5
C4—C5—C6	122.09 (12)	O2—C18—H18C	109.5
C4—C5—C10	118.74 (12)	H18A—C18—H18C	109.5
C6—C5—C10	119.15 (12)	H18B—C18—H18C	109.5
C7—C6—C5	120.89 (12)	O3—C19—H19A	109.5
C7—C6—H6	119.6	O3—C19—H19B	109.5
C5—C6—H6	119.6	H19A—C19—H19B	109.5
C6—C7—C8	119.88 (13)	O3—C19—H19C	109.5
C6—C7—H7	120.1	H19A—C19—H19C	109.5
C8—C7—H7	120.1	H19B—C19—H19C	109.5
O3—C8—C9	125.30 (12)	C13—C20—H20A	109.5
O3—C8—C7	113.68 (12)	C13—C20—H20B	109.5
C9—C8—C7	121.02 (13)	H20A—C20—H20B	109.5
C8—C9—C10	119.93 (12)	C13—C20—H20C	109.5
C8—C9—H9	120.0	H20A—C20—H20C	109.5
C10—C9—H9	120.0	H20B—C20—H20C	109.5
C1—C10—C9	122.29 (12)	C15—C21—H21A	109.5
C1—C10—C5	118.58 (13)	C15—C21—H21B	109.5
C9—C10—C5	119.12 (12)	H21A—C21—H21B	109.5
O1—C11—C3	122.83 (12)	C15—C21—H21C	109.5
O1—C11—C12	119.54 (12)	H21A—C21—H21C	109.5
C3—C11—C12	117.58 (11)	H21B—C21—H21C	109.5
C13—C12—C17	121.16 (13)	C17—C22—H22A	109.5
C13—C12—C11	119.32 (12)	C17—C22—H22B	109.5
C17—C12—C11	119.48 (12)	H22A—C22—H22B	109.5
C12—C13—C14	118.13 (13)	C17—C22—H22C	109.5
C12—C13—C20	121.43 (13)	H22A—C22—H22C	109.5
C14—C13—C20	120.43 (13)	H22B—C22—H22C	109.5
C15—C14—C13	122.01 (14)
C18—O2—C2—C1	−0.9 (3)	C4—C5—C10—C9	178.42 (12)
C18—O2—C2—C3	−179.40 (16)	C6—C5—C10—C9	−0.18 (19)
C10—C1—C2—O2	−179.68 (14)	C4—C3—C11—O1	154.26 (14)
C10—C1—C2—C3	−1.3 (2)	C2—C3—C11—O1	−21.7 (2)
O2—C2—C3—C4	177.30 (13)	C4—C3—C11—C12	−23.10 (18)
C1—C2—C3—C4	−1.2 (2)	C2—C3—C11—C12	160.89 (13)
O2—C2—C3—C11	−6.7 (2)	O1—C11—C12—C13	98.12 (16)
C1—C2—C3—C11	174.82 (13)	C3—C11—C12—C13	−84.42 (15)
C2—C3—C4—C5	2.7 (2)	O1—C11—C12—C17	−79.58 (17)
C11—C3—C4—C5	−173.52 (12)	C3—C11—C12—C17	97.88 (15)
C3—C4—C5—C6	176.92 (13)	C17—C12—C13—C14	1.18 (19)
C3—C4—C5—C10	−1.6 (2)	C11—C12—C13—C14	−176.48 (12)
C4—C5—C6—C7	−177.94 (13)	C17—C12—C13—C20	−179.81 (13)
C10—C5—C6—C7	0.6 (2)	C11—C12—C13—C20	2.53 (19)
C5—C6—C7—C8	−0.5 (2)	C12—C13—C14—C15	−1.3 (2)
C19—O3—C8—C9	0.1 (2)	C20—C13—C14—C15	179.64 (14)
C19—O3—C8—C7	179.45 (13)	C13—C14—C15—C16	0.3 (2)
C6—C7—C8—O3	−179.41 (13)	C13—C14—C15—C21	179.64 (13)
C6—C7—C8—C9	0.0 (2)	C14—C15—C16—C17	1.0 (2)
O3—C8—C9—C10	179.76 (12)	C21—C15—C16—C17	−178.38 (14)
C7—C8—C9—C10	0.5 (2)	C15—C16—C17—C12	−1.1 (2)
C2—C1—C10—C9	−176.96 (14)	C15—C16—C17—C22	178.19 (13)
C2—C1—C10—C5	2.4 (2)	C13—C12—C17—C16	0.0 (2)
C8—C9—C10—C1	178.97 (13)	C11—C12—C17—C16	177.66 (12)
C8—C9—C10—C5	−0.3 (2)	C13—C12—C17—C22	−179.30 (12)
C4—C5—C10—C1	−0.91 (19)	C11—C12—C17—C22	−1.64 (19)
C6—C5—C10—C1	−179.52 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.95	2.30	3.1123 (19)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.95	2.30	3.1123 (19)	143

Symmetry code: (i) .