(3,6-Dimeth­oxy­naphthalen-2-yl)(phen­yl)methanone

Kato, Y.; Takeuchi, R.; Muto, T.; Okamoto, A.; Yonezawa, N.

doi:10.1107/S1600536811005630

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o668

doi:10.1107/S1600536811005630

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(3,6-Dimethoxynaphthalen-2-yl)(phenyl)methanone

Yuichi Kato,^a Ryo Takeuchi,^a Toyokazu Muto,^a Akiko Okamoto ^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 12 February 2011; accepted 15 February 2011; online 19 February 2011)

In the title compound, C₁₉H₁₆O₃, 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 intermolecular C—H⋯O hydrogen bond exists between the H atom of one methoxy group and the O atom of the second methoxy group in an adjacent molecule. The crystal packing is additionally stabilized by a weak C—H⋯O intermolecular interaction 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_r = 292.32
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.098
S = 1.06
2735 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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) -x+2, -y, -z+1; (ii) x-1, y, z-1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811005630/fk2037sup1.cif

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

checkCIF report

Comment top

In the course of our study on selective electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene, peri-aroylnaphthalene compounds have proved to be formed regioselectively with the aid of suitable acidic mediator (Okamoto & Yonezawa, 2009). Recently, we have reported the structures of 1,8-diaroyl-2,7-dimethoxynaphthalenes such as 1,8-bis(4-methylbenzoyl)-2,7-dimethoxynaphthalene (Muto et al., 2010) and 1,8-bis(4-aminobenzoyl)-2,7-dimethoxynaphthalene (Nishijima et al., 2010). The aroyl groups at the 1,8-positions of the naphthalene rings in these compounds are bonded in a nearly perpendicular manner but the benzene rings of the aroyl groups tilt slightly toward the exo sides of the naphthalene rings. Such 1-aroylnaphthalene homologues as (2,7-dimethoxynaphthalen-1-yl)(3-nitrophenyl)methanone (Kataoka et al., 2010) are also revealed to have essentially the same non-coplanar structure as observed for 1,8-diaroylated naphthalenes. Furthermore, we reported the crystal structure analysis of the corresponding β-isomers of 3-aroyl-2,7-dimethoxynaphthalenes such as 2-(4-chlorobenzoyl)-3,6-dimethoxynaphthalene (Nakaema, Okamoto et al., 2008) and (4-fluorophenyl) (3,6-dimethoxy-2-naphthyl)methanone (Watanabe et al., 2010). In the 3-aroylated naphthalenes, which are generally regarded to be thermodynamically more stable than the corresponding 1-positioned isomeric molecules, the aroyl groups are connected to the naphthalene rings in a moderately twisted fashion. On the other hand, there are several unique structural features in the benzoylated naphthalene homologues, 1-benzoyl-2,7-dimethoxynaphthalene (Kato et al., 2010) and 1,8-dibenzoyl-2,7-dimethoxynaphthalene (Nakaema, Watanabe et al., 2008). 1-Benzoyl-2,7-dimethoxynaphthalene contains three independent conformers and each of them forms a columnar structure, respectively. As a part of our ongoing study on the synthesis and structure of these homologous molecules, the crystal structure analysis of the title compound, a 3-monoaroylnaphthalene, is discussed in this article.

The molecular structure of the title molecule is displayed in Fig. 1. The benzene group is bonded to the naphthalene ring with a non-coplanar configuration. The dihedral angle between the best planes of the benzene ring (C12—C17) and the naphthalene ring (C1—C10) is 68.32 (5)°. The bridging carbonyl plane (O1—C3—C11—C12) makes a relatively large dihedral angle of 54.32 (5)° with the naphthalene ring (C1—C10) [C2—C3—C11—O1 torsion angle = -125.86 (12)°], whereas it makes a rather small dihedral angle of 21.45 (6)° with benzene ring (C12—C17) [O1—C11—C12—C13 torsion angle = -156.47 (11)°].

The crystal packing exhibits a weak C—H···O intermolecular interaction between the oxygen atom of the carbonyl group and the hydrogen atom of the naphthalene ring (Table 1, Fig. 2). The packing is additionally stabilized by a C—H···O hydrogen bond between the hydrogen of the 2-methoxy group, which is situated adjacent to the benzoyl group, and the ethereal oxygen atom of the 7-methoxy group in the neighboring molecule (Table 1, Fig. 3).

Related literature top

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 top

A mixture of 2,7-dimethoxynaphthalene (3.74 g, 19.9 mmol), FeCl₃ (4.95 g, 37.1 mmol), trichloromethylbenzene (2.9 ml, 20 mmol) and dichloromethane (50 ml) was stirred at 293 K for 6 h, and the reaction mixture was poured into ice-cooled water followed by extraction with CHCl₃ (30 ml × 3). The combined extracts were washed with 2 M aqueous NaOH followed by washing with brine. The organic layer thus obtained was dried over anhydrous MgSO₄. The solvent was removed under reduced pressure to give cakes (yield 72%). The crude product was purified by flush silica gel chromatography (CHCl₃). Colorless platelet single crystals suitable for X-ray diffraction were obtained by crystallization from hexane and chloroform (yield 21%).

Spectroscopic Data:

¹H NMR δ (400 MHz, CDCl₃); 3.83 (3H, s), 3.95 (3H, s), 7.05 (1H, dd, J = 2.4, 9.2 Hz), 7.11 (1H, d, J = 2.4 Hz), 7.14 (1H, s), 7.44 (2H, t, J = 8.0 Hz), 7.56 (1H, t, J = 7.6 Hz), 7.69 (1H, d, J = 9.2 Hz), 7.78 (1H, s), 7.83–7.85 (2H, m) p.p.m..

¹³C NMR δ (75 MHz, CDCl₃); 55.34, 55.54, 105.00, 105.38, 117.02, 123.15, 127.89, 128.18, 129.93, 130.01, 130.07, 132.87, 137.11, 138.06, 155.83, 159.30, 196.02 p.p.m..

IR (KBr): 1627 (C═O), 1580, 1502 (Ar, naphthalene), 1213 cm^-1.

HRMS (m/z): [M + H]⁺ Calcd for C₁₉H₁₇O₃, 293.1178; found, 293.1203.

m.p. = 438.7–441.5 K.

Computing details top

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

Figures top

	Fig. 1. Molecular structure with displacement ellipsoids at 50% probability level for non-H atoms.
	Fig. 2. The C4—H4···O1 intermolecular interaction [symmetry code: (i) – x + 2, – y, – z + 1].
	Fig. 3. The C18—H18B···O3 intermolecular interaction [symmetry code: (ii) x – 1, y, z – 1].

(3,6-Dimethoxynaphthalen-2-yl)(phenyl)methanone top

Crystal data top

C₁₉H₁₆O₃	F(000) = 616
M_r = 292.32	D_x = 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

Data collection top

Rigaku R-AXIS RAPID diffractometer	2735 independent reflections
Radiation source: rotating anode	2509 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
Detector resolution: 10.000 pixels mm^-1	θ_max = 68.2°, θ_min = 4.3°
ω scans	h = −10→10
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −24→24
T_min = 0.677, T_max = 0.872	l = −10→10
26682 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)] = 0.034	H-atom parameters constrained
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0584P)² + 0.2227P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
2735 reflections	Δρ_max = 0.23 e Å⁻³
202 parameters	Δρ_min = −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)

Crystal data top

C₁₉H₁₆O₃	V = 1492.57 (6) Å³
M_r = 292.32	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 8.7186 (2) Å	µ = 0.71 mm⁻¹
b = 20.4650 (4) Å	T = 193 K
c = 8.5675 (2) Å	0.60 × 0.50 × 0.20 mm
β = 102.475 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2735 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	2509 reflections with I > 2σ(I)
T_min = 0.677, T_max = 0.872	R_int = 0.044
26682 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.06	Δρ_max = 0.23 e Å⁻³
2735 reflections	Δρ_min = −0.17 e Å⁻³
202 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	0.78878 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y, −z+1; (ii) x−1, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆O₃
M_r	292.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	8.7186 (2), 20.4650 (4), 8.5675 (2)
β (°)	102.475 (1)
V (Å³)	1492.57 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.71
Crystal size (mm)	0.60 × 0.50 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.677, 0.872
No. of measured, independent and observed [I > 2σ(I)] reflections	26682, 2735, 2509
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.098, 1.06
No. of reflections	2735
No. of parameters	202
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.17

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku, 2010), Il Milione (Burla et al., 2007), 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
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) −x+2, −y, −z+1; (ii) x−1, y, z−1.

Acknowledgements

The authors would express their gratitude to Professor Keiichi Noguchi, Instrumentation Analysis Center, Tokyo University of Agriculture & Technology, for technical advice. This work was partially supported by the Mukai Science and Technology Foundation, Tokyo, Japan.

References

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