2-(2,7-Dimeth­oxy-1-naphtho­yl)benzoic acid

Hijikata, D.; Nakaema, K.; Watanabe, S.; Okamoto, A.; Yonezawa, N.

doi:10.1107/S1600536810006847

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o713

doi:10.1107/S1600536810006847

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2-(2,7-Dimethoxy-1-naphthoyl)benzoic acid

Daichi Hijikata,^a Kosuke Nakaema,^a Shoji Watanabe,^a Akiko Okamoto ^a and Noriyuki Yonezawa ^a ^*

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

(Received 20 February 2010; accepted 23 February 2010; online 27 February 2010)

In the title compound, C₂₀H₁₆O₅, the dihedral angle between the naphthalene ring system and the benzene ring is 67.43 (5)°. The bridging carbonyl C—C(=O)—C plane makes dihedral angles of 82.64 (6) and 41.79 (7)°, respectively, with the naphthalene ring system and the benzene ring. The dihedral angle between the carboxy O—C(=O)—C plane and the benzene ring is 36.38 (7)° and that between the bridging carbonyl C—C(=O)—C plane and the carboxy O—C(=O)—C plane is 51.88 (8)°. The crystal structure is stabilized by intermolecular O—H⋯O and C—H⋯O hydrogen-bonding interactions. An intramolecular C—H⋯O hydrogen bond occurs between a naphthalene H atom and the carbonyl O atom of the carboxy group.

Related literature

For electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009 ). For related structures, see: Mitsui, Nakaema et al. (2008 ); Mitsui, Noguchi et al. (2009 ); Watanabe, Nakaema, Muto et al. (2010 ); Watanabe, Nakaema, Nishijima et al. (2010 ); Hijikata et al. (2010 ).

Experimental

Crystal data

C₂₀H₁₆O₅
M_r = 336.33
Monoclinic, P 2₁ /c
a = 10.8311 (2) Å
b = 10.61451 (19) Å
c = 15.4492 (3) Å
β = 111.728 (1)°
V = 1649.95 (5) Å³
Z = 4
Cu Kα radiation
μ = 0.81 mm⁻¹
T = 296 K
0.60 × 0.60 × 0.30 mm

Data collection

Rigaku R-AXIS- APID diffractometer
Absorption correction: multi-scan (NUMABS; Higashi, 1999 ) T_min = 0.711, T_max = 0.785
29727 measured reflections
3023 independent reflections
2710 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.095
S = 1.04
3023 reflections
233 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1⋯O1ⁱ	0.91 (2)	1.83 (2)	2.7320 (15)	173.4 (19)
C7—H7⋯O3ⁱⁱ	0.93	2.49	3.3215 (19)	150
C15—H15⋯O2ⁱⁱⁱ	0.93	2.48	3.3152 (16)	149
C17—H17⋯O5^iv	0.93	2.55	3.2821 (18)	136
C9—H9⋯O2	0.93	2.47	3.3850 (16)	169
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 global, I. DOI: 10.1107/S1600536810006847/om2323sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810006847/om2323Isup2.hkl

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). Recently, we reported the crystal structures of several 1,8-diaroylated naphthalene homologues exemplified by bis(4-bromobenzoyl)(2,7-dimethoxynaphthalene-1,8-diyl)dimethanone (Watanabe, Nakaema, Muto et al., 2010). The aroyl groups at the 1,8-positions of the naphthalene rings in these compounds are twisted almost perpendicularly but the benzene ring moieties of the aroyl groups tilt slightly toward the exo sides of the naphthalene rings. Moreover, the X-ray crystal structural analysis of 1-(4-substituted benzoylated)naphthalenes, i.e., 1-(4-chlorobenzoyl)-2,7-dimethoxynaphthalene (Mitsui et al., 2008), (4-chlorobenzoyl)(2-ethoxy-7-methoxynaphthalen-1-yl)methanone (Mitsui et al., 2009), 1-(4-nitrobenzoyl)-2,7-dimethoxynaphthalene (Watanabe, Nakaema, Nishijima et al., 2010) and methyl 4-(2,7-dimethoxy-1-naphthoyl)benzoate (Hijikata et al., 2010), has also revealed essentially the same non-coplanar structure as the 1,8-diaroylated naphthalenes.

As a part of our continuing study on the molecular structures of these homologous molecules, the crystal structure of title compound, 1-monoaroylnaphthalene bearing carboxy group, is discussed in this report.

In the molecule of the title compound, shown in Fig. 1, the dihedral angle between the naphthalene ring (C1—C10) and the benzene ring (C12—C17) is 67.43 (5)°. The bridging carbonyl C1—C11(=O1)—C12 plane makes dihedral angles of 82.64 (6)° [C2—C1—C11—O1 torsion angle = -77.60 (16)°] and 41.79 (7)° [O1—C11—C12—C13 torsion angle = -37.07 (17)°], respectively, with the naphthalene ring system and the benzene ring. The dihedral angle between the carboxy O3—C18(=O2)—C13 plane and the benzene ring is 36.38 (7)° [C12—C13—C18—O2 torsion angle = -35.33 (19)°]. The dihedral angle between the bridging carbonyl C1—C11(=O1)—C12 plane and the carboxy O3—C18(=O2)—C13 plane is 51.88 (8)°. The torsion angle between one methoxy group and the naphthalene ring plane is relatively large [C29—O4—C2—C3 = -15.3 (2)°] and that between the other methoxy group and the naphthalene ring plane is rather small [C20—O5—C8—C7 = 3.8 (2)°]. The crystal structure is stabilized by intermolecular O3—H1···O1ⁱ [symmetry code: (i) -x+1, y-1/2,-z+1/2] and C—H···O hydrogen-bonding interactions with one intramolecular C9—H9···O2 hydrogen bonding (Table 1, Fig 1, 2).

Related literature top

For electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009). For related structures, see: Mitsui, Nakaema et al. (2008); Mitsui, Noguchi et al. (2009); Watanabe, Nakaema, Muto et al. (2010); Watanabe, Nakaema, Nishijima et al. (2010); Hijikata et al. (2010).

Experimental top

The title compound was prepared by AlCl₃-mediated regioselective electrophilic aromatic aroylation of 2,7-dimethoxynaphthalene with acetic anhydride. Single crystals suitable for X-ray diffraction were obtained by recrystallization from diethyl ether.

Spectroscopic Data: ¹H NMR (300 MHz, CDCl₃) δ 3.65 (3H, s), 3.78 (3H, s), 7.00 (1H, dd, J = 2.4, 9.0 Hz), 7.43-7.58 (4H, m), 7.66 (1H, d, J = 9.0 Hz), 7.84-7.88 (2H, m); ¹³C NMR (75.0 MHz, CDCl₃) δ 55.3, 56.5, 102.7, 110.5, 117.4, 124.4, 129.4, 129.5, 129.9, 130.9, 131.4, 133.8, 142.1, 157.1, 159.6, 198.0; IR (KBr): 1698, 1627, 1512; HRMS (m/z): [M+H]⁺ Calcd for C₂₀H₁₇O_5, 337.1076; Found, 337.1057.

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, showing the atom-labeling scheme and 50% probability displacement ellipsoids. The intramolecular C—H···O interaction is shown as a dashed line.
	Fig. 2. A partial crystal packing diagram viewed down b. The intermolecular O—H···O and C—H···O interactions are shown as dashed lines.

2-(2,7-Dimethoxy-1-naphthoyl)benzoic acid top

Crystal data top

C₂₀H₁₆O₅	F(000) = 704
M_r = 336.33	D_x = 1.354 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ybc	Cell parameters from 26822 reflections
a = 10.8311 (2) Å	θ = 3.1–68.2°
b = 10.61451 (19) Å	µ = 0.81 mm⁻¹
c = 15.4492 (3) Å	T = 296 K
β = 111.728 (1)°	Block, colorless
V = 1649.95 (5) Å³	0.60 × 0.60 × 0.30 mm
Z = 4

Data collection top

Rigaku R-AXIS- APID diffractometer	3023 independent reflections
Radiation source: rotating anode	2710 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 10.00 pixels mm^-1	θ_max = 68.2°, θ_min = 4.4°
ω scans	h = −13→13
Absorption correction: multi-scan (NUMABS; Higashi, 1999)	k = −12→12
T_min = 0.711, T_max = 0.785	l = −18→18
29727 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0481P)² + 0.2862P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3023 reflections	Δρ_max = 0.16 e Å⁻³
233 parameters	Δρ_min = −0.12 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: 0.0021 (3)

Crystal data top

C₂₀H₁₆O₅	V = 1649.95 (5) Å³
M_r = 336.33	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 10.8311 (2) Å	µ = 0.81 mm⁻¹
b = 10.61451 (19) Å	T = 296 K
c = 15.4492 (3) Å	0.60 × 0.60 × 0.30 mm
β = 111.728 (1)°

Data collection top

Rigaku R-AXIS- APID diffractometer	3023 independent reflections
Absorption correction: multi-scan (NUMABS; Higashi, 1999)	2710 reflections with I > 2σ(I)
T_min = 0.711, T_max = 0.785	R_int = 0.028
29727 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.16 e Å⁻³
3023 reflections	Δρ_min = −0.12 e Å⁻³
233 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.40529 (9)	0.47494 (10)	0.24166 (7)	0.0630 (3)
O2	0.36166 (9)	0.19907 (10)	0.24736 (6)	0.0647 (3)
O3	0.54599 (9)	0.15634 (11)	0.36707 (7)	0.0709 (3)
H1	0.5589 (19)	0.100 (2)	0.3272 (14)	0.104 (6)*
O4	0.30544 (10)	0.73160 (9)	0.28563 (8)	0.0726 (3)
O5	−0.05580 (10)	0.17144 (10)	0.06622 (8)	0.0725 (3)
C1	0.18889 (11)	0.54939 (12)	0.21895 (8)	0.0487 (3)
C2	0.18877 (13)	0.67861 (13)	0.22803 (10)	0.0580 (3)
C3	0.07232 (16)	0.74830 (15)	0.18184 (12)	0.0706 (4)
H3	0.0716	0.8349	0.1906	0.085*
C4	−0.03897 (15)	0.68890 (15)	0.12452 (11)	0.0707 (4)
H4	−0.1149	0.7362	0.0937	0.085*
C5	−0.04262 (13)	0.55796 (14)	0.11051 (9)	0.0590 (3)
C6	−0.15566 (13)	0.49476 (17)	0.04818 (11)	0.0711 (4)
H6	−0.2311	0.5412	0.0148	0.085*
C7	−0.15665 (14)	0.36879 (17)	0.03601 (11)	0.0710 (4)
H7	−0.2324	0.3292	−0.0048	0.085*
C8	−0.04226 (12)	0.29720 (14)	0.08549 (9)	0.0576 (3)
C9	0.06985 (11)	0.35343 (12)	0.14630 (9)	0.0505 (3)
H9	0.1442	0.3050	0.1787	0.061*
C10	0.07285 (11)	0.48552 (12)	0.16004 (8)	0.0495 (3)
C11	0.31457 (11)	0.47747 (11)	0.27012 (8)	0.0447 (3)
C12	0.33101 (10)	0.41688 (11)	0.36061 (7)	0.0409 (3)
C13	0.40131 (10)	0.30406 (11)	0.39141 (7)	0.0402 (3)
C14	0.43259 (12)	0.26655 (13)	0.48298 (8)	0.0511 (3)
H14	0.4795	0.1921	0.5037	0.061*
C15	0.39508 (14)	0.33816 (15)	0.54409 (9)	0.0605 (4)
H15	0.4171	0.3121	0.6055	0.073*
C16	0.32540 (13)	0.44760 (14)	0.51365 (9)	0.0607 (4)
H16	0.3004	0.4960	0.5546	0.073*
C17	0.29207 (12)	0.48650 (12)	0.42223 (9)	0.0523 (3)
H17	0.2431	0.5600	0.4019	0.063*
C18	0.43300 (11)	0.21726 (11)	0.32640 (7)	0.0424 (3)
C19	0.32145 (18)	0.86387 (15)	0.28282 (13)	0.0792 (5)
H19A	0.4114	0.8861	0.3201	0.095*
H19B	0.2620	0.9052	0.3069	0.095*
H19C	0.3017	0.8900	0.2196	0.095*
C20	0.05113 (17)	0.09279 (16)	0.11674 (13)	0.0798 (5)
H20A	0.0300	0.0072	0.0966	0.096*
H20B	0.0671	0.0990	0.1820	0.096*
H20C	0.1293	0.1185	0.1061	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0532 (5)	0.0731 (6)	0.0744 (6)	0.0134 (4)	0.0372 (5)	0.0261 (5)
O2	0.0577 (5)	0.0842 (7)	0.0423 (5)	0.0184 (5)	0.0068 (4)	−0.0127 (4)
O3	0.0549 (5)	0.0910 (8)	0.0539 (5)	0.0303 (5)	0.0051 (4)	−0.0173 (5)
O4	0.0693 (6)	0.0470 (5)	0.0925 (8)	−0.0002 (5)	0.0194 (6)	0.0074 (5)
O5	0.0589 (6)	0.0676 (6)	0.0757 (7)	−0.0136 (5)	0.0073 (5)	0.0077 (5)
C1	0.0445 (6)	0.0497 (7)	0.0544 (7)	0.0074 (5)	0.0212 (5)	0.0128 (5)
C2	0.0566 (8)	0.0524 (7)	0.0659 (8)	0.0054 (6)	0.0238 (6)	0.0107 (6)
C3	0.0750 (10)	0.0527 (8)	0.0863 (10)	0.0201 (7)	0.0326 (8)	0.0185 (7)
C4	0.0591 (8)	0.0723 (10)	0.0796 (10)	0.0264 (7)	0.0245 (8)	0.0246 (8)
C5	0.0472 (7)	0.0696 (9)	0.0616 (8)	0.0142 (6)	0.0216 (6)	0.0198 (6)
C6	0.0434 (7)	0.0907 (12)	0.0713 (9)	0.0153 (7)	0.0121 (6)	0.0229 (8)
C7	0.0430 (7)	0.0918 (12)	0.0670 (9)	−0.0025 (7)	0.0073 (6)	0.0146 (8)
C8	0.0459 (7)	0.0673 (8)	0.0574 (7)	−0.0049 (6)	0.0165 (6)	0.0115 (6)
C9	0.0398 (6)	0.0567 (7)	0.0531 (7)	0.0037 (5)	0.0151 (5)	0.0141 (5)
C10	0.0411 (6)	0.0580 (7)	0.0518 (6)	0.0067 (5)	0.0200 (5)	0.0138 (5)
C11	0.0402 (6)	0.0435 (6)	0.0520 (6)	−0.0009 (5)	0.0190 (5)	0.0036 (5)
C12	0.0340 (5)	0.0447 (6)	0.0449 (6)	−0.0026 (4)	0.0154 (4)	−0.0013 (5)
C13	0.0345 (5)	0.0464 (6)	0.0388 (5)	−0.0007 (4)	0.0125 (4)	−0.0013 (4)
C14	0.0502 (7)	0.0599 (7)	0.0410 (6)	0.0052 (6)	0.0143 (5)	0.0036 (5)
C15	0.0610 (8)	0.0820 (10)	0.0397 (6)	0.0000 (7)	0.0200 (6)	−0.0030 (6)
C16	0.0622 (8)	0.0724 (9)	0.0560 (7)	−0.0029 (7)	0.0319 (6)	−0.0168 (6)
C17	0.0493 (7)	0.0511 (7)	0.0623 (7)	0.0009 (5)	0.0274 (6)	−0.0056 (6)
C18	0.0383 (5)	0.0476 (6)	0.0398 (6)	0.0030 (5)	0.0128 (5)	0.0003 (5)
C19	0.0928 (12)	0.0515 (8)	0.0992 (12)	−0.0041 (8)	0.0423 (10)	0.0056 (8)
C20	0.0753 (10)	0.0634 (9)	0.0870 (11)	−0.0022 (8)	0.0142 (8)	−0.0008 (8)

Geometric parameters (Å, º) top

O1—C11	1.2163 (13)	C8—C9	1.3670 (18)
O2—C18	1.1945 (13)	C9—C10	1.4166 (18)
O3—C18	1.3195 (14)	C9—H9	0.9300
O3—H1	0.91 (2)	C11—C12	1.4885 (16)
O4—C2	1.3684 (17)	C12—C17	1.3884 (16)
O4—C19	1.4173 (18)	C12—C13	1.4042 (16)
O5—C8	1.3637 (18)	C13—C14	1.3856 (16)
O5—C20	1.4065 (19)	C13—C18	1.4935 (15)
C1—C2	1.3788 (19)	C14—C15	1.3849 (18)
C1—C10	1.4215 (17)	C14—H14	0.9300
C1—C11	1.5046 (15)	C15—C16	1.370 (2)
C2—C3	1.4074 (19)	C15—H15	0.9300
C3—C4	1.358 (2)	C16—C17	1.3850 (19)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.405 (2)	C17—H17	0.9300
C4—H4	0.9300	C19—H19A	0.9600
C5—C6	1.415 (2)	C19—H19B	0.9600
C5—C10	1.4256 (16)	C19—H19C	0.9600
C6—C7	1.350 (2)	C20—H20A	0.9600
C6—H6	0.9300	C20—H20B	0.9600
C7—C8	1.4126 (19)	C20—H20C	0.9600
C7—H7	0.9300

C18—O3—H1	110.5 (12)	C12—C11—C1	118.89 (9)
C2—O4—C19	118.76 (12)	C17—C12—C13	119.07 (10)
C8—O5—C20	117.39 (11)	C17—C12—C11	116.93 (11)
C2—C1—C10	120.37 (11)	C13—C12—C11	123.23 (10)
C2—C1—C11	119.08 (11)	C14—C13—C12	119.21 (10)
C10—C1—C11	120.53 (11)	C14—C13—C18	118.63 (10)
O4—C2—C1	116.08 (12)	C12—C13—C18	121.94 (9)
O4—C2—C3	123.52 (13)	C15—C14—C13	121.04 (12)
C1—C2—C3	120.37 (14)	C15—C14—H14	119.5
C4—C3—C2	119.94 (14)	C13—C14—H14	119.5
C4—C3—H3	120.0	C16—C15—C14	119.65 (12)
C2—C3—H3	120.0	C16—C15—H15	120.2
C3—C4—C5	121.82 (13)	C14—C15—H15	120.2
C3—C4—H4	119.1	C15—C16—C17	120.35 (12)
C5—C4—H4	119.1	C15—C16—H16	119.8
C4—C5—C6	122.79 (13)	C17—C16—H16	119.8
C4—C5—C10	118.80 (13)	C16—C17—C12	120.65 (12)
C6—C5—C10	118.40 (13)	C16—C17—H17	119.7
C7—C6—C5	121.64 (13)	C12—C17—H17	119.7
C7—C6—H6	119.2	O2—C18—O3	122.85 (11)
C5—C6—H6	119.2	O2—C18—C13	124.36 (10)
C6—C7—C8	119.83 (14)	O3—C18—C13	112.69 (9)
C6—C7—H7	120.1	O4—C19—H19A	109.5
C8—C7—H7	120.1	O4—C19—H19B	109.5
O5—C8—C9	125.01 (12)	H19A—C19—H19B	109.5
O5—C8—C7	113.99 (13)	O4—C19—H19C	109.5
C9—C8—C7	121.00 (14)	H19A—C19—H19C	109.5
C8—C9—C10	120.03 (11)	H19B—C19—H19C	109.5
C8—C9—H9	120.0	O5—C20—H20A	109.5
C10—C9—H9	120.0	O5—C20—H20B	109.5
C9—C10—C1	122.26 (10)	H20A—C20—H20B	109.5
C9—C10—C5	119.11 (12)	O5—C20—H20C	109.5
C1—C10—C5	118.59 (12)	H20A—C20—H20C	109.5
O1—C11—C12	119.88 (10)	H20B—C20—H20C	109.5
O1—C11—C1	121.07 (10)

C19—O4—C2—C1	166.64 (13)	C6—C5—C10—C9	−0.91 (18)
C19—O4—C2—C3	−15.3 (2)	C4—C5—C10—C1	−2.41 (18)
C10—C1—C2—O4	−179.44 (11)	C6—C5—C10—C1	176.71 (12)
C11—C1—C2—O4	−1.13 (18)	C2—C1—C11—O1	−77.60 (16)
C10—C1—C2—C3	2.4 (2)	C10—C1—C11—O1	100.70 (14)
C11—C1—C2—C3	−179.30 (12)	C2—C1—C11—C12	97.80 (14)
O4—C2—C3—C4	178.89 (14)	C10—C1—C11—C12	−83.90 (14)
C1—C2—C3—C4	−3.1 (2)	O1—C11—C12—C17	132.79 (12)
C2—C3—C4—C5	1.0 (2)	C1—C11—C12—C17	−42.67 (15)
C3—C4—C5—C6	−177.30 (14)	O1—C11—C12—C13	−37.07 (17)
C3—C4—C5—C10	1.8 (2)	C1—C11—C12—C13	147.48 (11)
C4—C5—C6—C7	−179.97 (15)	C17—C12—C13—C14	−1.43 (16)
C10—C5—C6—C7	0.9 (2)	C11—C12—C13—C14	168.22 (11)
C5—C6—C7—C8	−0.7 (2)	C17—C12—C13—C18	173.01 (10)
C20—O5—C8—C9	3.8 (2)	C11—C12—C13—C18	−17.34 (16)
C20—O5—C8—C7	−176.41 (14)	C12—C13—C14—C15	0.31 (18)
C6—C7—C8—O5	−179.36 (14)	C18—C13—C14—C15	−174.32 (11)
C6—C7—C8—C9	0.4 (2)	C13—C14—C15—C16	0.3 (2)
O5—C8—C9—C10	179.34 (12)	C14—C15—C16—C17	0.2 (2)
C7—C8—C9—C10	−0.4 (2)	C15—C16—C17—C12	−1.4 (2)
C8—C9—C10—C1	−176.87 (11)	C13—C12—C17—C16	1.96 (17)
C8—C9—C10—C5	0.67 (18)	C11—C12—C17—C16	−168.33 (11)
C2—C1—C10—C9	177.90 (12)	C14—C13—C18—O2	139.14 (13)
C11—C1—C10—C9	−0.38 (17)	C12—C13—C18—O2	−35.33 (18)
C2—C1—C10—C5	0.35 (17)	C14—C13—C18—O3	−37.23 (15)
C11—C1—C10—C5	−177.93 (11)	C12—C13—C18—O3	148.30 (11)
C4—C5—C10—C9	179.96 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O1ⁱ	0.91 (2)	1.83 (2)	2.7320 (15)	173.4 (19)
C7—H7···O3ⁱⁱ	0.93	2.49	3.3215 (19)	150
C15—H15···O2ⁱⁱⁱ	0.93	2.48	3.3152 (16)	149
C17—H17···O5^iv	0.93	2.55	3.2821 (18)	136
C9—H9···O2	0.93	2.47	3.3850 (16)	169

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1, −y+1/2, z−1/2; (iii) x, −y+1/2, z+1/2; (iv) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆O₅
M_r	336.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.8311 (2), 10.61451 (19), 15.4492 (3)
β (°)	111.728 (1)
V (Å³)	1649.95 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.81
Crystal size (mm)	0.60 × 0.60 × 0.30

Data collection
Diffractometer	Rigaku R-AXIS- APID diffractometer
Absorption correction	Multi-scan (NUMABS; Higashi, 1999)
T_min, T_max	0.711, 0.785
No. of measured, independent and observed [I > 2σ(I)] reflections	29727, 3023, 2710
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.095, 1.04
No. of reflections	3023
No. of parameters	233
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.12

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
O3—H1···O1ⁱ	0.91 (2)	1.83 (2)	2.7320 (15)	173.4 (19)
C7—H7···O3ⁱⁱ	0.93	2.49	3.3215 (19)	150
C15—H15···O2ⁱⁱⁱ	0.93	2.48	3.3152 (16)	149
C17—H17···O5^iv	0.93	2.55	3.2821 (18)	136
C9—H9···O2	0.93	2.47	3.3850 (16)	169

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1, −y+1/2, z−1/2; (iii) x, −y+1/2, z+1/2; (iv) −x, y+1/2, −z+1/2.

Acknowledgements

The authors would express their gratitude to Professor Keiichi Noguchi for his technical advice. This work was partially supported by the Ogasawara Foundation for the Promotion of Science & Engineering, Tokyo, Japan.

References

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