(2-Hy­droxy-7-meth­oxy­naphthalen-1-yl)(phen­yl)methanone

Nagasawa, A.; Mitsui, R.; Kato, Y.; Okamoto, A.; Yonezawa, N.

doi:10.1107/S1600536810038547

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2677

doi:10.1107/S1600536810038547

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(2-Hydroxy-7-methoxynaphthalen-1-yl)(phenyl)methanone

Atsushi Nagasawa,^a Ryosuke Mitsui,^a Yuichi Kato,^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: yonezawa@cc.tuat.ac.jp

(Received 25 September 2010; accepted 27 September 2010; online 30 September 2010)

In the molecule of the title compound, C₁₈H₁₄O₃, there is an intramolecular O—H⋯O=C hydrogen bond between the carbonyl and hydroxy groups on the naphthalene ring system. The angles between the C=O bond vector and the least-squares planes of the naphthalene ring system and the phenyl ring are 30.58 (6) and 42.82 (7)°, respectively, while the dihedral angle between the naphthalene ring system and the phenyl ring is 58.65 (5)°. In the crystal, molecules are connected by pairs of intermolecular O—H⋯O=C hydrogen bonds, forming centrosymmetric dimers.

Related literature

For closely related structures, see: Hijikata et al. (2010 ); Kato et al. (2010 ); Mitsui et al. (2009 ); Mitsui, Nakaema, Noguchi, Okamoto & Yonezawa (2008 ); Mitsui, Nakaema, Noguchi & Yonezawa (2008 ).

Experimental

Crystal data

C₁₈H₁₄O₃
M_r = 278.29
Monoclinic, P 2₁ /c
a = 9.81012 (18) Å
b = 6.27891 (11) Å
c = 22.0737 (4) Å
β = 93.167 (1)°
V = 1357.59 (4) Å³
Z = 4
Cu Kα radiation
μ = 0.75 mm⁻¹
T = 193 K
0.60 × 0.40 × 0.40 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ) T_min = 0.586, T_max = 0.754
20565 measured reflections
2496 independent reflections
2244 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.103
S = 1.08
2496 reflections
196 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3	0.92 (2)	1.77 (2)	2.5792 (14)	145 (2)
O1—H1⋯O3ⁱ	0.92 (2)	2.32 (2)	3.0088 (16)	132.4 (18)
Symmetry code: (i) -x+1, -y+1, -z+1.

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 global, I. DOI: 10.1107/S1600536810038547/is2606sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810038547/is2606Isup2.hkl

checkCIF report

Comment top

Recently, we reported the crystal structures of several 1-aroylated 2,7-dimethoxynaphthalene homologues exemplified by 1-benzoyl-2,7-dimethoxynaphthalene (Kato et al., 2010) and 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Mitsui, Nakaema, Noguchi, Okamoto & Yonezawa, 2008). Methyl 4-(2,7-dimethoxy-1-naphthoyl)benzoate (Hijikata et al., 2010). Furthermore, we also reported the crystal structure of 1-monoaroylnaphthalene derivatives having 2-oxy group exemplified by (4-chlorobenzoyl)(2-hydroxy-7-methoxynaphthalene-1-yl)metanone (Mitsui, Nakaema, Noguchi & Yonezawa, 2008) and (4-chlorophenyl)(2-ethoxy-7-methoxynaphthalen-1-yl)methanone (Mitsui et al., 2009). As a part of our ongoing studies on the synthesis and crystal structure analysis of aroylated naphthalene derivatives, we prepared and analysed the crystal structure of 1-benzoyl-2-hydroxy-7-methoxynaphthalene (I). The title compound was prepared by chemoselective demethylation of 1-benzoyl-2,7-dimethoxynaphthalene with aluminium trichloride.

An ORTEPIII (Burnett & Johnson, 1996) plot of (I) is shown in Fig. 1. In the molecule of (I), the intramolecular O—H···O═C hydrogen bond that forms a six-membered ring including carbonyl and hydroxy groups on the naphthalene ring is observed [O3···H1 = 1.77 (2) Å]. The conformation of these groups resembles to that of (4-chlorobenzoyl)(2-hydroxy-7-methoxynaphthalen-1-yl)metanone (Mitsui, Nakaema, Noguchi & Yonezawa, 2008). The angles of C═O bond vector against the least-squares plane of the naphthalene ring (C1–C10) and benzene ring (C12–C17) are 30.58 (6) and 42.82 (7)°, respectively. The dihedral angle between the naphthalene ring (C1–C10) and benzene ring (C12–C17) is 58.65 (5)°.

In the crystal structure, the molecular packing of (I) is mainly stabilized by intermolecular hydrogen bond and van der Waals interaction. Two adjacent naphthalene rings are exactly parallel and the intermolecular O—H···O═C hydrogen bond between the hydroxy group and the carbonyl oxygen on the naphthalene ring (Fig. 2) along the c axis, is observed [O3···H1 = 2.32 (2) Å]. The oxygen atom in the methoxy group interacts with carbon atom in the methoxy group of the next molecule, i.e. two methoxy groups in the adjacent molecules interact with each other [O2···C18 = 3.060 (2) Å] along the a axis. The naphthalene rings interact with the carbonyl groups [C4···O3 = 3.036 (18) Å] along the b axis. The benzoyl groups interact with the methyl groups (C16···H18A = 2.88 Å) along the a axis.

Related literature top

For closely related structures, see: Hijikata et al. (2010); Kato et al. (2010); Mitsui et al. (2009); Mitsui, Nakaema, Noguchi, Okamoto & Yonezawa (2008); Mitsui, Nakaema, Noguchi & Yonezawa (2008).

Experimental top

To a solution of 1-benzoyl-2,7-dimethoxynaphthalene (2.92 g, 10 mmol) in CH₂Cl₂ (100 ml) was added AlCl₃ (6.65 g, 50 mmol). The reaction mixture was refluxed for 30 min giving a dark red solution, which was then poured into H₂O (30 ml). The aqueous layer was extracted with CHCl₃(30 ml × 3). The combined organic layers were washed with brine (30 ml × 3), and dried over MgSO₄ overnight. The solvent was removed in vacuo and the crude material was purified by recrystallization from hexane to give compound (I) as yellow platelets (m.p. 371.8–372.3 K, yield 1.45 g, 52%).

Spectroscopic Data: ¹H NMR (300 MHz, CDCl₃) δ 11.64 (s, 1H), 7.85 (d, 1H), 7.64–7.60 (m, 3H), 7.55 (tt, 1H), 7.43 (t, 2H) 7.08 (d, 1H), 6.89 (dd, 1H), 6.59 (d, 1H), 3.27 (s, 3H); ¹³C NMR (75 MHz, CDCl₃) δ 200.8, 162.8, 158.2, 140.8, 136.5, 134.1, 132.3, 130.1, 129.14, 128.8, 123.7, 116.5, 115.9, 113.7, 106.5, 54.5; IR (KBr): 3446, 1617, 1572, 1511, 1200; HRMS (m/z): [M + H]⁺ calcd for C₁₈H₁₅O₃, 279.1021; found, 279.0999.

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 asymmetric unit of compound (I), showing 50% probability displacement ellipsoids. The dashed line indicates an intramolecular O—H···O hydrogen bond.
	Fig. 2. A partial crystal packing diagram of compound (I), viewed down the b axis. The dashed lines indicate intra- and intermolecular O—H···O hydrogen bonds.

(2-Hydroxy-7-methoxynaphthalen-1-yl)(phenyl)methanone top

Crystal data top

C₁₈H₁₄O₃	F(000) = 584
M_r = 278.29	D_x = 1.362 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 371.8–372.3 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54187 Å
a = 9.81012 (18) Å	Cell parameters from 19252 reflections
b = 6.27891 (11) Å	θ = 4.0–68.2°
c = 22.0737 (4) Å	µ = 0.75 mm⁻¹
β = 93.167 (1)°	T = 193 K
V = 1357.59 (4) Å³	Block, yellow
Z = 4	0.60 × 0.40 × 0.40 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2496 independent reflections
Radiation source: rotating anode	2244 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 10.00 pixels mm^-1	θ_max = 68.2°, θ_min = 4.0°
ω scans	h = −11→11
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −7→7
T_min = 0.586, T_max = 0.754	l = −26→26
20565 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)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.103	w = 1/[σ²(F_o²) + (0.0535P)² + 0.3346P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
2496 reflections	Δρ_max = 0.23 e Å⁻³
196 parameters	Δρ_min = −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: 0.0146 (8)

Crystal data top

C₁₈H₁₄O₃	V = 1357.59 (4) Å³
M_r = 278.29	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 9.81012 (18) Å	µ = 0.75 mm⁻¹
b = 6.27891 (11) Å	T = 193 K
c = 22.0737 (4) Å	0.60 × 0.40 × 0.40 mm
β = 93.167 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2496 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	2244 reflections with I > 2σ(I)
T_min = 0.586, T_max = 0.754	R_int = 0.038
20565 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.23 e Å⁻³
2496 reflections	Δρ_min = −0.16 e Å⁻³
196 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	0.37752 (10)	0.17334 (19)	0.46905 (5)	0.0478 (3)
O2	0.84529 (10)	−0.02213 (17)	0.22739 (4)	0.0442 (3)
O3	0.57091 (10)	0.44133 (17)	0.45195 (5)	0.0482 (3)
C1	0.55482 (12)	0.1185 (2)	0.39823 (5)	0.0336 (3)
C2	0.43388 (13)	0.0609 (2)	0.42511 (6)	0.0387 (3)
C3	0.36518 (14)	−0.1302 (3)	0.40877 (7)	0.0451 (4)
H3	0.2846	−0.1684	0.4281	0.054*
C4	0.41359 (14)	−0.2593 (2)	0.36562 (7)	0.0431 (3)
H4	0.3685	−0.3902	0.3564	0.052*
C5	0.53019 (13)	−0.2030 (2)	0.33398 (6)	0.0363 (3)
C6	0.57599 (14)	−0.3323 (2)	0.28681 (6)	0.0407 (3)
H6	0.5321	−0.4647	0.2784	0.049*
C7	0.68125 (14)	−0.2718 (2)	0.25323 (6)	0.0401 (3)
H7	0.7113	−0.3612	0.2219	0.048*
C8	0.74557 (13)	−0.0737 (2)	0.26554 (6)	0.0356 (3)
C9	0.70639 (13)	0.0537 (2)	0.31195 (6)	0.0335 (3)
H9	0.7512	0.1860	0.3194	0.040*
C10	0.59982 (12)	−0.0095 (2)	0.34895 (5)	0.0322 (3)
C11	0.63086 (13)	0.3022 (2)	0.42425 (5)	0.0341 (3)
C12	0.78243 (13)	0.3247 (2)	0.42242 (5)	0.0327 (3)
C13	0.87010 (14)	0.1539 (2)	0.43450 (6)	0.0383 (3)
H13	0.8342	0.0163	0.4417	0.046*
C14	1.01009 (14)	0.1857 (2)	0.43590 (7)	0.0443 (4)
H14	1.0701	0.0698	0.4448	0.053*
C15	1.06297 (14)	0.3852 (3)	0.42446 (7)	0.0469 (4)
H15	1.1590	0.4054	0.4246	0.056*
C16	0.97576 (15)	0.5548 (2)	0.41281 (7)	0.0456 (4)
H16	1.0119	0.6917	0.4049	0.055*
C17	0.83608 (14)	0.5257 (2)	0.41259 (6)	0.0392 (3)
H17	0.7766	0.6437	0.4057	0.047*
C18	0.92146 (16)	0.1669 (3)	0.24071 (8)	0.0527 (4)
H18A	0.9894	0.1867	0.2103	0.063*
H18B	0.9679	0.1545	0.2810	0.063*
H18C	0.8595	0.2894	0.2400	0.063*
H1	0.428 (2)	0.296 (4)	0.4744 (11)	0.092 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0369 (5)	0.0601 (7)	0.0471 (6)	0.0032 (5)	0.0080 (4)	−0.0043 (5)
O2	0.0435 (5)	0.0478 (6)	0.0420 (5)	0.0003 (4)	0.0081 (4)	−0.0093 (4)
O3	0.0490 (6)	0.0453 (6)	0.0514 (6)	0.0042 (5)	0.0132 (5)	−0.0117 (5)
C1	0.0324 (6)	0.0356 (7)	0.0322 (6)	0.0041 (5)	−0.0032 (5)	0.0025 (5)
C2	0.0322 (6)	0.0468 (8)	0.0367 (7)	0.0046 (6)	−0.0011 (5)	0.0032 (6)
C3	0.0328 (7)	0.0543 (9)	0.0480 (8)	−0.0039 (6)	0.0004 (6)	0.0071 (7)
C4	0.0377 (7)	0.0415 (8)	0.0489 (8)	−0.0063 (6)	−0.0083 (6)	0.0064 (6)
C5	0.0349 (6)	0.0344 (7)	0.0384 (7)	0.0014 (5)	−0.0089 (5)	0.0028 (5)
C6	0.0409 (7)	0.0329 (7)	0.0466 (8)	−0.0003 (6)	−0.0116 (6)	−0.0035 (6)
C7	0.0422 (7)	0.0368 (7)	0.0402 (7)	0.0069 (6)	−0.0075 (6)	−0.0092 (6)
C8	0.0334 (6)	0.0389 (7)	0.0340 (6)	0.0055 (5)	−0.0030 (5)	−0.0017 (5)
C9	0.0340 (6)	0.0319 (7)	0.0340 (6)	0.0009 (5)	−0.0038 (5)	−0.0022 (5)
C10	0.0309 (6)	0.0327 (7)	0.0322 (6)	0.0041 (5)	−0.0061 (5)	0.0021 (5)
C11	0.0396 (7)	0.0343 (7)	0.0286 (6)	0.0055 (5)	0.0023 (5)	0.0011 (5)
C12	0.0376 (7)	0.0337 (7)	0.0265 (6)	0.0011 (5)	−0.0024 (5)	−0.0046 (5)
C13	0.0421 (7)	0.0337 (7)	0.0385 (7)	0.0010 (6)	−0.0040 (5)	−0.0017 (6)
C14	0.0406 (7)	0.0465 (8)	0.0449 (8)	0.0083 (6)	−0.0063 (6)	−0.0019 (6)
C15	0.0367 (7)	0.0582 (9)	0.0454 (8)	−0.0040 (7)	−0.0014 (6)	−0.0033 (7)
C16	0.0480 (8)	0.0428 (8)	0.0457 (8)	−0.0097 (6)	0.0001 (6)	0.0011 (6)
C17	0.0458 (8)	0.0333 (7)	0.0381 (7)	0.0025 (6)	−0.0031 (6)	−0.0023 (6)
C18	0.0512 (9)	0.0552 (10)	0.0531 (9)	−0.0099 (7)	0.0163 (7)	−0.0085 (7)

Geometric parameters (Å, º) top

O1—C2	1.3434 (17)	C8—C9	1.3716 (18)
O1—H1	0.92 (2)	C9—C10	1.4184 (18)
O2—C8	1.3646 (16)	C9—H9	0.9500
O2—C18	1.4244 (18)	C11—C12	1.4964 (18)
O3—C11	1.2340 (16)	C12—C17	1.3895 (19)
C1—C2	1.4029 (18)	C12—C13	1.3908 (18)
C1—C10	1.4414 (18)	C13—C14	1.386 (2)
C1—C11	1.4728 (18)	C13—H13	0.9500
C2—C3	1.413 (2)	C14—C15	1.384 (2)
C3—C4	1.357 (2)	C14—H14	0.9500
C3—H3	0.9500	C15—C16	1.381 (2)
C4—C5	1.418 (2)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.382 (2)
C5—C6	1.413 (2)	C16—H16	0.9500
C5—C10	1.4233 (18)	C17—H17	0.9500
C6—C7	1.358 (2)	C18—H18A	0.9800
C6—H6	0.9500	C18—H18B	0.9800
C7—C8	1.4138 (19)	C18—H18C	0.9800
C7—H7	0.9500

C2—O1—H1	107.2 (15)	C9—C10—C1	123.00 (12)
C8—O2—C18	117.15 (11)	C5—C10—C1	119.21 (11)
C2—C1—C10	118.47 (12)	O3—C11—C1	120.18 (12)
C2—C1—C11	117.33 (12)	O3—C11—C12	116.62 (12)
C10—C1—C11	124.15 (11)	C1—C11—C12	123.10 (11)
O1—C2—C1	124.13 (13)	C17—C12—C13	119.65 (12)
O1—C2—C3	114.90 (12)	C17—C12—C11	118.39 (11)
C1—C2—C3	120.91 (13)	C13—C12—C11	121.80 (12)
C4—C3—C2	120.41 (13)	C14—C13—C12	119.65 (13)
C4—C3—H3	119.8	C14—C13—H13	120.2
C2—C3—H3	119.8	C12—C13—H13	120.2
C3—C4—C5	121.32 (13)	C15—C14—C13	120.45 (13)
C3—C4—H4	119.3	C15—C14—H14	119.8
C5—C4—H4	119.3	C13—C14—H14	119.8
C6—C5—C4	121.16 (13)	C16—C15—C14	119.80 (13)
C6—C5—C10	119.56 (12)	C16—C15—H15	120.1
C4—C5—C10	119.26 (13)	C14—C15—H15	120.1
C7—C6—C5	121.57 (13)	C15—C16—C17	120.20 (14)
C7—C6—H6	119.2	C15—C16—H16	119.9
C5—C6—H6	119.2	C17—C16—H16	119.9
C6—C7—C8	119.07 (13)	C16—C17—C12	120.21 (13)
C6—C7—H7	120.5	C16—C17—H17	119.9
C8—C7—H7	120.5	C12—C17—H17	119.9
O2—C8—C9	124.22 (12)	O2—C18—H18A	109.5
O2—C8—C7	114.70 (12)	O2—C18—H18B	109.5
C9—C8—C7	121.07 (12)	H18A—C18—H18B	109.5
C8—C9—C10	120.84 (12)	O2—C18—H18C	109.5
C8—C9—H9	119.6	H18A—C18—H18C	109.5
C10—C9—H9	119.6	H18B—C18—H18C	109.5
C9—C10—C5	117.70 (12)

C10—C1—C2—O1	−176.30 (12)	C6—C5—C10—C1	−178.29 (11)
C11—C1—C2—O1	6.22 (19)	C4—C5—C10—C1	3.48 (18)
C10—C1—C2—C3	6.53 (19)	C2—C1—C10—C9	168.90 (12)
C11—C1—C2—C3	−170.95 (12)	C11—C1—C10—C9	−13.80 (19)
O1—C2—C3—C4	−178.91 (13)	C2—C1—C10—C5	−7.45 (17)
C1—C2—C3—C4	−1.5 (2)	C11—C1—C10—C5	169.85 (11)
C2—C3—C4—C5	−2.7 (2)	C2—C1—C11—O3	−25.19 (18)
C3—C4—C5—C6	−176.55 (13)	C10—C1—C11—O3	157.48 (12)
C3—C4—C5—C10	1.7 (2)	C2—C1—C11—C12	150.82 (12)
C4—C5—C6—C7	175.00 (13)	C10—C1—C11—C12	−26.50 (18)
C10—C5—C6—C7	−3.20 (19)	O3—C11—C12—C17	−42.07 (17)
C5—C6—C7—C8	−0.6 (2)	C1—C11—C12—C17	141.79 (12)
C18—O2—C8—C9	6.22 (19)	O3—C11—C12—C13	133.31 (13)
C18—O2—C8—C7	−174.85 (12)	C1—C11—C12—C13	−42.84 (18)
C6—C7—C8—O2	−176.72 (12)	C17—C12—C13—C14	−0.74 (19)
C6—C7—C8—C9	2.25 (19)	C11—C12—C13—C14	−176.06 (12)
O2—C8—C9—C10	178.76 (11)	C12—C13—C14—C15	−1.0 (2)
C7—C8—C9—C10	−0.11 (19)	C13—C14—C15—C16	1.4 (2)
C8—C9—C10—C5	−3.58 (18)	C14—C15—C16—C17	0.0 (2)
C8—C9—C10—C1	−179.98 (11)	C15—C16—C17—C12	−1.8 (2)
C6—C5—C10—C9	5.17 (17)	C13—C12—C17—C16	2.1 (2)
C4—C5—C10—C9	−173.06 (12)	C11—C12—C17—C16	177.61 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.92 (2)	1.77 (2)	2.5792 (14)	145 (2)
O1—H1···O3ⁱ	0.92 (2)	2.32 (2)	3.0088 (16)	132.4 (18)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄O₃
M_r	278.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	9.81012 (18), 6.27891 (11), 22.0737 (4)
β (°)	93.167 (1)
V (Å³)	1357.59 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.75
Crystal size (mm)	0.60 × 0.40 × 0.40

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Numerical (NUMABS; Higashi, 1999)
T_min, T_max	0.586, 0.754
No. of measured, independent and observed [I > 2σ(I)] reflections	20565, 2496, 2244
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.103, 1.08
No. of reflections	2496
No. of parameters	196
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.16

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
O1—H1···O3	0.92 (2)	1.77 (2)	2.5792 (14)	145 (2)
O1—H1···O3ⁱ	0.92 (2)	2.32 (2)	3.0088 (16)	132.4 (18)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors would express their gratitude to Professor Keiichi Noguchi for technical advice. This work was partially supported by a Sasagawa Scientific research grant from the Japan Science Society.

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
Hijikata, D., Nakaema, K., Watanabe, S., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o554. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kato, Y., Nagasawa, A., Hijikata, D., Okamoto, A. & Yonezawa, N. (2010). Acta Cryst. E66, o2659. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mitsui, R., Nakaema, K., Noguchi, K., Okamoto, A. & Yonezawa, N. (2008). Acta Cryst. E64, o1278. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mitsui, R., Nakaema, K., Noguchi, K. & Yonezawa, N. (2008). Acta Cryst. E64, o2497. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mitsui, R., Noguchi, K. & Yonezawa, N. (2009). Acta Cryst. E65, o543. Web of Science CSD CrossRef IUCr Journals 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