(3,6-Dimeth­oxy­naphthalen-2-yl)(2,4,6-trimethyl­phen­yl)methanone

Muto, T.; Sasagawa, K.; Okamoto, A.; Oike, H.; Yonezawa, N.

doi:10.1107/S1600536811042401

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3062

doi:10.1107/S1600536811042401

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(3,6-Dimethoxynaphthalen-2-yl)(2,4,6-trimethylphenyl)methanone

Toyokazu Muto,^a Kosuke Sasagawa,^a Akiko Okamoto,^a ^* Hideaki Oike ^a and Noriyuki Yonezawa ^a

^aDepartment of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-machi, Koganei, Tokyo 184-8588, Japan
^*Correspondence e-mail: aokamoto@cc.tuat.ac.jp

(Received 1 October 2011; accepted 13 October 2011; online 29 October 2011)

In the title compound, C₂₂H₂₂O₃, 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 intermolecular C—H⋯O interactions link molecules 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_r = 334.40
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.043
wR(F²) = 0.130
S = 1.04
3310 reflections
232 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811042401/rz2647sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811042401/rz2647Isup3.cml

checkCIF report

Comment top

In the course of our study on electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, peri-aroylnaphthalene compounds have proven to be formed regioselectively with the aid of suitable acidic mediators (Okamoto & Yonezawa, 2009; Okamoto et al., 2011). Recently, we have reported the crystal structures of several 1,8-diaroylated naphthalene analogues exemplified by 1,8-bis(4-methylbenzoyl)-2,7-dimethoxynaphthalene (Muto et al., 2010). The aroyl groups at the 1,8-positions of the naphthalene rings in these compounds are connected in an almost perpendicular fashion. Besides, the crystal structures of 1-monoaroylated naphthalene derivatives and the β-isomers of 3-monoaroylated naphthalene derivatives have been also clarified such as (2,7-dimethoxynaphthalen-1-yl)(2,4,6-trimethylphenyl)methanone (Muto et al., 2011), (3,6-dimethoxynaphthalen-2-yl)(phenyl)methanone (Kato et al., 2011) and (4-bromophenyl)(3,6-dimethoxy-2-naphthyl)methanone (Kato et al., 2010). As a part of our continuing study on the molecular structures of these homologous molecules, the crystal structure of title compound, 3-monoaroylnaphthalene bearing three methyl groups, is discussed in this report.

The molecular structure of the title compound is displayed in Fig. 1. The 2,4,6-trimethylphenyl group is situated out of the plane of the naphthalene ring. The dihedral angle between the best planes of the 2,4,6-trimethylphenyl ring (C12—C17) and the naphthalene ring (C1—C10) is 79.95 (5)°. The carbonyl moiety attaches almost coplanarly to the naphthalene ring rather than the benzene ring. The bridging carbonyl C—C(═O)—C plane makes dihedral angles of 24.21 (7) and 82.43 (8)°, respectively, with the naphthalene ring system and the benzene ring. The dihedral angle of the title compound between the bridging carbonyl plane and the naphthalene ring is smaller than those in 3-monoaroylated naphthalene analogues, (3,6-dimethoxynaphthalen-2-yl)(phenyl)methanone (Kato et al., 2011) and (4-bromophenyl)(3,6-dimethoxy-2-naphthyl)methanone [54.32 (5) and 47.07 (9)°, respectively]. The carbonyl group makes torsion angles of 21.8 (2) and -98.12 (16)°, respectively, with the naphthalene ring and the benzene ring [C2—C3—C11—O1 torsion angle = 21.8 (2)°; O1—C11—C12—C13 torsion angle = -98.12 (16)°].

In the crystal structure, the molecular packing of the title compound is stabilized mainly by van der Waals interactions. The crystal packing is additionally stabilized by intermolecular C—H···O hydrogen bonding between the oxygen atom (O1) of the carbonyl group and one hydrogen atom (H6) of the naphthalene ring of the adjacent molecule along the c axis (Fig. 2; Table 1).

Related literature top

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 top

To a 100 ml flask, 2,4,6-trimethylbenzoyl chloride (30.0 mmol, 5.48 g), titanium chloride (90.0 mmol, 17.1 g) and methylene chloride (25 ml) were placed and stirred at rt. To the reaction mixture thus obtained, 2,7-dimethoxynaphthalene (10.0 mmol, 1.88 g) was added. After the reaction mixture was stirred at rt for 24 h, it was poured into ice-cold water (50 ml). The aqueous layer was extracted with CHCl₃ (20 ml × 3). The combined extracts were washed with 2 M aqueous NaOH followed by washing with brine. The organic layers thus obtained were dried over anhydrous MgSO₄. The solvent was removed under reduced pressure to give cake. The crude product was purified by recrystallization from hexane and CHCl₃ (yield 56%). Colourless platelet single crystals suitable for X-ray diffraction were obtained by repeated crystallization from hexane/CHCl₃ mixtures (3:1 v/v).

¹H NMR δ (300 MHz, CDCl₃); 2.14 (6H, s), 2.33 (3H, s), 3.92 (6H, s), 6.87 (2H, s), 6.98 (1H, dd, J = 2.4, 8.7 Hz), 7.04 (1H, d, J = 2.4 Hz), 7.12 (1H, s), 7.61 (1H, d, J = 9.0 Hz), 7.90 (1H, s) ppm.

¹³C NMR δ (75 MHz, CDCl₃); 19.50, 21.12, 55.31, 55.82, 104.68, 106.17, 117.21, 122.93, 126.94, 128.31, 130.81, 134.06, 134.23, 138.10, 138.51, 139.18, 157.13, 160.25, 199.32 ppm.

IR (KBr); 1673 (C=O), 1626, 1499, 1470 (Ar, naphthalene), 1212 (=C—O—C) cm^-1

HRMS (m/z); [M + H]⁺ Calcd for C₂₂H₂₃O₃, 335.1647; found, 335.1640.

m.p. = 423.0–424.5 K

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Intermolecular C6—H6···O1ⁱ interactions, viewed along the b axis [symmetry code: (i) x, -y + 1/2, z + 1/2].

(3,6-Dimethoxynaphthalen-2-yl)(2,4,6-trimethylphenyl)methanone top

Crystal data top

C₂₂H₂₂O₃	F(000) = 712
M_r = 334.40	D_x = 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

Data collection top

Rigaku R-AXIS RAPID diffractometer	3310 independent reflections
Radiation source: rotating anode	3047 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 10.000 pixels mm^-1	θ_max = 68.2°, θ_min = 3.1°
ω scans	h = −18→18
Absorption correction: numerical (NUMABS; Higashi 1999)	k = −9→9
T_min = 0.701, T_max = 0.939	l = −18→18
32532 measured reflections

Refinement top

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(F_o²) + (0.0753P)² + 0.4568P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3310 reflections	Δρ_max = 0.24 e Å⁻³
232 parameters	Δρ_min = −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)

Crystal data top

C₂₂H₂₂O₃	V = 1820.49 (13) Å³
M_r = 334.40	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 15.4205 (2) Å	µ = 0.64 mm⁻¹
b = 8.23702 (10) Å	T = 193 K
c = 15.3832 (2) Å	0.60 × 0.20 × 0.10 mm
β = 111.30 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3310 independent reflections
Absorption correction: numerical (NUMABS; Higashi 1999)	3047 reflections with I > 2σ(I)
T_min = 0.701, T_max = 0.939	R_int = 0.035
32532 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.04	Δρ_max = 0.24 e Å⁻³
3310 reflections	Δρ_min = −0.21 e Å⁻³
232 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₂O₃
M_r	334.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	15.4205 (2), 8.23702 (10), 15.3832 (2)
β (°)	111.30 (1)
V (Å³)	1820.49 (13)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.64
Crystal size (mm)	0.60 × 0.20 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi 1999)
T_min, T_max	0.701, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	32532, 3310, 3047
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.130, 1.04
No. of reflections	3310
No. of parameters	232
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.21

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z+1/2.

Acknowledgements

The authors express their gratitude to Master Daichi Hijikata, Department of Organic and Polymer Materials Chemistry, Graduate School, Tokyo University of Agriculture and Technology, and Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture and Technology, for their technical advice.

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Higashi, T. (1999). NUMABS. Rigaku Corporation, Tokyo, Japan. Google Scholar
Kato, Y., Nagasawa, A., Kataoka, K., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2795. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kato, Y., Takeuchi, R., Muto, T., Okamoto, A. & Yonezawa, N. (2011). Acta Cryst. E67, o668. Web of Science CSD CrossRef IUCr Journals Google Scholar
Muto, T., Kato, Y., Nagasawa, A., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2752. Web of Science CSD CrossRef IUCr Journals Google Scholar
Muto, T., Sasagawa, K., Okamoto, A., Oike, H. & Yonezawa, N. (2011). Acta Cryst. E67, o2813. Web of Science CSD CrossRef IUCr Journals Google Scholar
Okamoto, A., Mitsui, R., Oike, H. & Yonezawa, N. (2011). Chem. Lett. 40, 1283–1284. Web of Science CrossRef CAS Google Scholar
Okamoto, A. & Yonezawa, N. (2009). Chem. Lett. 38, 914–915. Web of Science CrossRef CAS Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar