Dimethyl 3,3-dimeth­oxy-4,4′-methyl­ene­di-2-naphthoate

He, R.; Gao, E.; Gu, S.-J.; Qin, D.-B.

doi:10.1107/S1600536807033909

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Dimethyl 3,3-dimethoxy-4,4′-methylenedi-2-naphthoate

R. He, E. Gao, S.-J. Gu and D.-B. Qin

In the title compound, C₂₇H₂₄O₆, the two naphthalene ring systems are nearly perpendicular to one another with a dihedral angle of 87.77 (2)°. The molecular structure is stabilized by several C—H

O intramolecular hydrogen bonds. In the crystal structure, inversion-related molecules are linked through π–π interactions [centroid–centroid distance = 3.6311 (6) Å and perpendicular distance between unsubstituted aromatic rings = 3.476 Å] between the naphthalene ring systems and also by C—H

π interactions. In addition, C—H

O intermolecular interactions are observed.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033909/ci2414sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033909/ci2414Isup2.hkl Contains datablock I

CCDC reference: 657774

checkCIF report

Key indicators

Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.002 Å
R factor = 0.036
wR factor = 0.099
Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.62 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Pamoic acid or its derivatives or analogs are used in the pharmaceutical industry for the preparation of medicaments for the treatment of diseases characterized by deposits of amyloid aggregates. We report here the crystal structure of the title compound.

Bond lengths and angles in the title molecule (Fig. 1) are within normal ranges. Both naphthalene ring systems are slightly non-planar, with the dihedral angle between the two benzene rings being 5.06 (4)° for the C1—C10 ring system and 3.92 (3)° for the C15—C24 ring system. The two naphthalene ring systems are almost perpendicular, with a dihedral angle of 87.77 (2)°.

The molecular structure is stabilized by C—H···O hydrogen bonds (Table 1). The crystal structure is stabilized by π-π interactions between the naphthalene ring systems of the inversion related molecules, with a Cg1···Cg1ⁱ distance of 3.6311 (6) Å [symmetry code: (i) 1 - x, 1 - y, 1 - z] where Cg1 is the C4—C9 ring centroid. In addition, weak C—H···O intermolecular hydrogen bonds and C—H···π interactions involving the C15/C16/C21—C24 ring (centroid Cg2) are observed (Table 1).

Related literature top

For synthesis, see: Georghiou et al. (1996). For related structures, see: Haynes et al. (2006) and Liu et al. (2006).

Experimental top

The title compound was prepared according to the reported procedure of Georghiou et al. (1996). Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from dichloromethane.

Structure description top

For synthesis, see: Georghiou et al. (1996). For related structures, see: Haynes et al. (2006) and Liu et al. (2006).

Computing details top

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.

Dimethyl 3,3-dimethoxy-4,4'-methylenedi-2-naphthoate top

Crystal data top

C₂₇H₂₄O₆	F(000) = 936
M_r = 444.46	D_x = 1.351 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 19190 reflections
a = 12.9871 (4) Å	θ = 3.0–27.5°
b = 20.0999 (5) Å	µ = 0.10 mm⁻¹
c = 8.7466 (3) Å	T = 153 K
β = 106.798 (1)°	Block, colourless
V = 2185.78 (11) Å³	0.59 × 0.58 × 0.58 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	4617 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.021
Graphite monochromator	θ_max = 27.5°, θ_min = 3.2°
ω scans	h = −14→16
21180 measured reflections	k = −25→26
5007 independent reflections	l = −11→11

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-atom parameters constrained
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.056P)² + 0.7416P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
5007 reflections	Δρ_max = 0.33 e Å⁻³
303 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0128 (11)

Crystal data top

C₂₇H₂₄O₆	V = 2185.78 (11) Å³
M_r = 444.46	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.9871 (4) Å	µ = 0.10 mm⁻¹
b = 20.0999 (5) Å	T = 153 K
c = 8.7466 (3) Å	0.59 × 0.58 × 0.58 mm
β = 106.798 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4617 reflections with I > 2σ(I)
21180 measured reflections	R_int = 0.021
5007 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.01	Δρ_max = 0.33 e Å⁻³
5007 reflections	Δρ_min = −0.20 e Å⁻³
303 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	0.08724 (6)	0.39859 (4)	0.27018 (9)	0.02037 (17)
O2	0.25890 (7)	0.35292 (4)	−0.02411 (9)	0.02536 (18)
O3	0.14283 (7)	0.29602 (4)	0.07285 (9)	0.02582 (18)
O4	0.27501 (6)	0.52935 (4)	0.87194 (8)	0.01955 (16)
O5	0.42601 (7)	0.69099 (5)	0.89705 (11)	0.0326 (2)
O6	0.30271 (7)	0.66608 (4)	1.02247 (10)	0.0298 (2)
C1	0.19780 (8)	0.39958 (5)	0.33629 (12)	0.0168 (2)
C2	0.26229 (8)	0.37440 (5)	0.24159 (12)	0.0180 (2)
C3	0.37214 (8)	0.38001 (5)	0.29508 (12)	0.0197 (2)
H3	0.4143	0.3669	0.2278	0.024*
C4	0.42325 (8)	0.40517 (5)	0.44938 (12)	0.0184 (2)
C5	0.53713 (8)	0.40633 (5)	0.50967 (13)	0.0226 (2)
H5	0.5795	0.3926	0.4431	0.027*
C6	0.58662 (9)	0.42690 (6)	0.66216 (14)	0.0251 (2)
H6	0.6629	0.4274	0.7014	0.030*
C7	0.52378 (9)	0.44744 (5)	0.76095 (13)	0.0235 (2)
H7	0.5582	0.4608	0.8677	0.028*
C8	0.41346 (8)	0.44845 (5)	0.70490 (12)	0.0197 (2)
H8	0.3728	0.4629	0.7732	0.024*
C9	0.35920 (8)	0.42820 (5)	0.54631 (12)	0.0165 (2)
C10	0.24400 (8)	0.42940 (5)	0.48266 (11)	0.01613 (19)
C11	0.03374 (9)	0.34490 (6)	0.32574 (15)	0.0265 (2)
H11A	0.0530	0.3025	0.2859	0.032*
H11B	−0.0443	0.3513	0.2863	0.032*
H11C	0.0561	0.3444	0.4428	0.032*
C12	0.21234 (8)	0.33737 (5)	0.09015 (12)	0.0188 (2)
C13	0.22256 (10)	0.31315 (6)	−0.16796 (13)	0.0273 (2)
H13A	0.2351	0.2660	−0.1407	0.033*
H13B	0.2625	0.3259	−0.2429	0.033*
H13C	0.1456	0.3207	−0.2175	0.033*
C14	0.17457 (8)	0.46359 (5)	0.57397 (12)	0.01689 (19)
H14A	0.0979	0.4546	0.5187	0.020*
H14B	0.1911	0.4441	0.6823	0.020*
C15	0.19164 (8)	0.53865 (5)	0.58891 (11)	0.01617 (19)
C16	0.15427 (8)	0.58152 (5)	0.45237 (12)	0.0166 (2)
C17	0.08944 (8)	0.55826 (5)	0.30175 (12)	0.0196 (2)
H17	0.0715	0.5124	0.2881	0.024*
C18	0.05245 (9)	0.60128 (6)	0.17562 (13)	0.0226 (2)
H18	0.0080	0.5849	0.0767	0.027*
C19	0.07947 (9)	0.66946 (6)	0.19073 (13)	0.0247 (2)
H19	0.0548	0.6984	0.1018	0.030*
C20	0.14131 (9)	0.69356 (5)	0.33394 (13)	0.0229 (2)
H20	0.1590	0.7395	0.3442	0.028*
C21	0.17943 (8)	0.65081 (5)	0.46755 (12)	0.0179 (2)
C22	0.24206 (8)	0.67646 (5)	0.61591 (12)	0.0192 (2)
H22	0.2636	0.7218	0.6244	0.023*
C23	0.27166 (8)	0.63584 (5)	0.74749 (12)	0.0178 (2)
C24	0.24304 (8)	0.56738 (5)	0.73454 (11)	0.01641 (19)
C25	0.19433 (9)	0.52489 (6)	0.95462 (13)	0.0262 (2)
H25A	0.1782	0.5695	0.9866	0.031*
H25B	0.2210	0.4970	1.0498	0.031*
H25C	0.1288	0.5051	0.8839	0.031*
C26	0.33310 (9)	0.66448 (5)	0.90516 (13)	0.0205 (2)
C27	0.48928 (11)	0.72350 (7)	1.04184 (18)	0.0421 (3)
H27A	0.4460	0.7583	1.0722	0.051*
H27B	0.5534	0.7435	1.0231	0.051*
H27C	0.5112	0.6907	1.1280	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0163 (4)	0.0186 (4)	0.0240 (4)	−0.0002 (3)	0.0023 (3)	−0.0011 (3)
O2	0.0339 (4)	0.0249 (4)	0.0193 (4)	−0.0056 (3)	0.0107 (3)	−0.0059 (3)
O3	0.0295 (4)	0.0255 (4)	0.0205 (4)	−0.0067 (3)	0.0042 (3)	−0.0030 (3)
O4	0.0234 (4)	0.0196 (4)	0.0162 (3)	0.0032 (3)	0.0066 (3)	0.0020 (3)
O5	0.0227 (4)	0.0363 (5)	0.0373 (5)	−0.0077 (3)	0.0063 (3)	−0.0119 (4)
O6	0.0398 (5)	0.0280 (4)	0.0219 (4)	−0.0035 (3)	0.0092 (3)	−0.0062 (3)
C1	0.0170 (5)	0.0138 (4)	0.0187 (5)	0.0009 (3)	0.0038 (4)	0.0012 (3)
C2	0.0222 (5)	0.0144 (4)	0.0169 (4)	0.0007 (4)	0.0050 (4)	−0.0004 (3)
C3	0.0220 (5)	0.0181 (5)	0.0209 (5)	0.0014 (4)	0.0090 (4)	−0.0018 (4)
C4	0.0187 (5)	0.0163 (4)	0.0206 (5)	0.0009 (4)	0.0062 (4)	0.0001 (4)
C5	0.0191 (5)	0.0242 (5)	0.0256 (5)	0.0014 (4)	0.0082 (4)	−0.0023 (4)
C6	0.0164 (5)	0.0291 (6)	0.0278 (5)	0.0004 (4)	0.0035 (4)	−0.0014 (4)
C7	0.0228 (5)	0.0246 (5)	0.0201 (5)	0.0008 (4)	0.0015 (4)	−0.0023 (4)
C8	0.0216 (5)	0.0185 (5)	0.0186 (5)	0.0029 (4)	0.0051 (4)	−0.0010 (4)
C9	0.0180 (5)	0.0130 (4)	0.0183 (5)	0.0010 (3)	0.0050 (4)	0.0007 (3)
C10	0.0185 (5)	0.0127 (4)	0.0176 (4)	0.0010 (3)	0.0059 (4)	0.0010 (3)
C11	0.0212 (5)	0.0240 (5)	0.0354 (6)	−0.0051 (4)	0.0101 (4)	−0.0036 (4)
C12	0.0216 (5)	0.0162 (5)	0.0173 (5)	0.0034 (4)	0.0037 (4)	0.0006 (3)
C13	0.0348 (6)	0.0291 (6)	0.0182 (5)	−0.0013 (5)	0.0077 (4)	−0.0067 (4)
C14	0.0176 (5)	0.0156 (4)	0.0185 (4)	0.0002 (3)	0.0067 (4)	−0.0009 (3)
C15	0.0155 (4)	0.0156 (4)	0.0189 (5)	0.0019 (3)	0.0075 (4)	0.0000 (3)
C16	0.0149 (4)	0.0184 (5)	0.0183 (5)	0.0031 (3)	0.0075 (4)	0.0005 (4)
C17	0.0185 (5)	0.0200 (5)	0.0209 (5)	0.0022 (4)	0.0066 (4)	−0.0014 (4)
C18	0.0196 (5)	0.0288 (6)	0.0187 (5)	0.0030 (4)	0.0042 (4)	−0.0001 (4)
C19	0.0238 (5)	0.0269 (5)	0.0231 (5)	0.0041 (4)	0.0061 (4)	0.0084 (4)
C20	0.0225 (5)	0.0204 (5)	0.0268 (5)	0.0015 (4)	0.0084 (4)	0.0061 (4)
C21	0.0164 (4)	0.0188 (5)	0.0204 (5)	0.0024 (4)	0.0082 (4)	0.0020 (4)
C22	0.0194 (5)	0.0163 (4)	0.0237 (5)	0.0003 (4)	0.0090 (4)	−0.0003 (4)
C23	0.0167 (4)	0.0179 (5)	0.0197 (5)	0.0012 (3)	0.0068 (4)	−0.0023 (4)
C24	0.0162 (4)	0.0166 (4)	0.0176 (4)	0.0029 (3)	0.0067 (4)	0.0007 (3)
C25	0.0307 (6)	0.0294 (6)	0.0218 (5)	−0.0025 (4)	0.0126 (4)	0.0014 (4)
C26	0.0214 (5)	0.0146 (4)	0.0238 (5)	0.0028 (4)	0.0037 (4)	−0.0018 (4)
C27	0.0305 (6)	0.0385 (7)	0.0486 (8)	−0.0085 (5)	−0.0023 (6)	−0.0164 (6)

Geometric parameters (Å, º) top

O1—C1	1.3843 (12)	C11—H11C	0.98
O1—C11	1.4419 (13)	C13—H13A	0.98
O2—C12	1.3459 (13)	C13—H13B	0.98
O2—C13	1.4497 (12)	C13—H13C	0.98
O3—C12	1.2040 (13)	C14—C15	1.5250 (13)
O4—C24	1.3829 (11)	C14—H14A	0.99
O4—C25	1.4377 (13)	C14—H14B	0.99
O5—C26	1.3396 (14)	C15—C24	1.3821 (13)
O5—C27	1.4507 (15)	C15—C16	1.4385 (13)
O6—C26	1.2015 (13)	C16—C17	1.4219 (14)
C1—C10	1.3836 (13)	C16—C21	1.4280 (14)
C1—C2	1.4299 (14)	C17—C18	1.3745 (14)
C2—C3	1.3715 (14)	C17—H17	0.95
C2—C12	1.4943 (13)	C18—C19	1.4114 (16)
C3—C4	1.4142 (14)	C18—H18	0.95
C3—H3	0.95	C19—C20	1.3665 (16)
C4—C5	1.4196 (14)	C19—H19	0.95
C4—C9	1.4257 (14)	C20—C21	1.4194 (14)
C5—C6	1.3665 (15)	C20—H20	0.95
C5—H5	0.95	C21—C22	1.4146 (14)
C6—C7	1.4108 (16)	C22—C23	1.3724 (14)
C6—H6	0.95	C22—H22	0.95
C7—C8	1.3738 (15)	C23—C24	1.4213 (14)
C7—H7	0.95	C23—C26	1.4946 (14)
C8—C9	1.4217 (14)	C25—H25A	0.98
C8—H8	0.95	C25—H25B	0.98
C9—C10	1.4379 (13)	C25—H25C	0.98
C10—C14	1.5295 (13)	C27—H27A	0.98
C11—H11A	0.98	C27—H27B	0.98
C11—H11B	0.98	C27—H27C	0.98

C1—O1—C11	114.37 (8)	C15—C14—H14A	108.9
C12—O2—C13	114.39 (8)	C10—C14—H14A	108.9
C24—O4—C25	113.09 (8)	C15—C14—H14B	108.9
C26—O5—C27	115.13 (10)	C10—C14—H14B	108.9
C10—C1—O1	120.85 (9)	H14A—C14—H14B	107.7
C10—C1—C2	121.29 (9)	C24—C15—C16	118.17 (9)
O1—C1—C2	117.60 (9)	C24—C15—C14	120.79 (9)
C3—C2—C1	119.93 (9)	C16—C15—C14	121.04 (9)
C3—C2—C12	119.05 (9)	C17—C16—C21	117.72 (9)
C1—C2—C12	120.86 (9)	C17—C16—C15	122.66 (9)
C2—C3—C4	120.66 (9)	C21—C16—C15	119.59 (9)
C2—C3—H3	119.7	C18—C17—C16	120.86 (10)
C4—C3—H3	119.7	C18—C17—H17	119.6
C3—C4—C5	120.78 (9)	C16—C17—H17	119.6
C3—C4—C9	119.34 (9)	C17—C18—C19	121.06 (10)
C5—C4—C9	119.86 (9)	C17—C18—H18	119.5
C6—C5—C4	120.88 (10)	C19—C18—H18	119.5
C6—C5—H5	119.6	C20—C19—C18	119.62 (10)
C4—C5—H5	119.6	C20—C19—H19	120.2
C5—C6—C7	119.61 (10)	C18—C19—H19	120.2
C5—C6—H6	120.2	C19—C20—C21	120.86 (10)
C7—C6—H6	120.2	C19—C20—H20	119.6
C8—C7—C6	120.93 (10)	C21—C20—H20	119.6
C8—C7—H7	119.5	C22—C21—C20	120.39 (9)
C6—C7—H7	119.5	C22—C21—C16	119.75 (9)
C7—C8—C9	121.04 (9)	C20—C21—C16	119.86 (9)
C7—C8—H8	119.5	C23—C22—C21	119.99 (9)
C9—C8—H8	119.5	C23—C22—H22	120.0
C8—C9—C4	117.60 (9)	C21—C22—H22	120.0
C8—C9—C10	122.67 (9)	C22—C23—C24	120.38 (9)
C4—C9—C10	119.72 (9)	C22—C23—C26	119.35 (9)
C1—C10—C9	118.39 (9)	C24—C23—C26	120.26 (9)
C1—C10—C14	120.95 (9)	C15—C24—O4	120.91 (9)
C9—C10—C14	120.66 (8)	C15—C24—C23	121.57 (9)
O1—C11—H11A	109.5	O4—C24—C23	117.38 (9)
O1—C11—H11B	109.5	O4—C25—H25A	109.5
H11A—C11—H11B	109.5	O4—C25—H25B	109.5
O1—C11—H11C	109.5	H25A—C25—H25B	109.5
H11A—C11—H11C	109.5	O4—C25—H25C	109.5
H11B—C11—H11C	109.5	H25A—C25—H25C	109.5
O3—C12—O2	123.26 (9)	H25B—C25—H25C	109.5
O3—C12—C2	124.95 (9)	O6—C26—O5	123.90 (10)
O2—C12—C2	111.68 (9)	O6—C26—C23	125.36 (10)
O2—C13—H13A	109.5	O5—C26—C23	110.69 (9)
O2—C13—H13B	109.5	O5—C27—H27A	109.5
H13A—C13—H13B	109.5	O5—C27—H27B	109.5
O2—C13—H13C	109.5	H27A—C27—H27B	109.5
H13A—C13—H13C	109.5	O5—C27—H27C	109.5
H13B—C13—H13C	109.5	H27A—C27—H27C	109.5
C15—C14—C10	113.34 (8)	H27B—C27—H27C	109.5

C11—O1—C1—C10	−84.36 (11)	C10—C14—C15—C24	−109.68 (10)
C11—O1—C1—C2	101.37 (10)	C10—C14—C15—C16	70.68 (11)
C10—C1—C2—C3	−0.43 (15)	C24—C15—C16—C17	−172.29 (9)
O1—C1—C2—C3	173.81 (9)	C14—C15—C16—C17	7.37 (14)
C10—C1—C2—C12	174.96 (9)	C24—C15—C16—C21	5.58 (13)
O1—C1—C2—C12	−10.80 (13)	C14—C15—C16—C21	−174.77 (9)
C1—C2—C3—C4	5.60 (15)	C21—C16—C17—C18	−0.05 (14)
C12—C2—C3—C4	−169.88 (9)	C15—C16—C17—C18	177.86 (9)
C2—C3—C4—C5	175.19 (10)	C16—C17—C18—C19	1.32 (16)
C2—C3—C4—C9	−3.41 (15)	C17—C18—C19—C20	−1.53 (17)
C3—C4—C5—C6	−176.06 (10)	C18—C19—C20—C21	0.45 (16)
C9—C4—C5—C6	2.54 (16)	C19—C20—C21—C22	−179.06 (10)
C4—C5—C6—C7	−0.18 (17)	C19—C20—C21—C16	0.81 (15)
C5—C6—C7—C8	−1.44 (17)	C17—C16—C21—C22	178.87 (9)
C6—C7—C8—C9	0.66 (16)	C15—C16—C21—C22	0.89 (14)
C7—C8—C9—C4	1.67 (15)	C17—C16—C21—C20	−1.01 (14)
C7—C8—C9—C10	−179.14 (10)	C15—C16—C21—C20	−178.98 (9)
C3—C4—C9—C8	175.39 (9)	C20—C21—C22—C23	175.03 (9)
C5—C4—C9—C8	−3.22 (14)	C16—C21—C22—C23	−4.84 (14)
C3—C4—C9—C10	−3.82 (14)	C21—C22—C23—C24	2.27 (15)
C5—C4—C9—C10	177.56 (9)	C21—C22—C23—C26	−176.94 (9)
O1—C1—C10—C9	179.26 (8)	C16—C15—C24—O4	176.06 (8)
C2—C1—C10—C9	−6.68 (14)	C14—C15—C24—O4	−3.59 (14)
O1—C1—C10—C14	−1.45 (14)	C16—C15—C24—C23	−8.33 (14)
C2—C1—C10—C14	172.60 (9)	C14—C15—C24—C23	172.02 (9)
C8—C9—C10—C1	−170.44 (9)	C25—O4—C24—C15	−90.58 (11)
C4—C9—C10—C1	8.74 (14)	C25—O4—C24—C23	93.63 (10)
C8—C9—C10—C14	10.28 (14)	C22—C23—C24—C15	4.53 (15)
C4—C9—C10—C14	−170.55 (9)	C26—C23—C24—C15	−176.27 (9)
C13—O2—C12—O3	−3.15 (15)	C22—C23—C24—O4	−179.71 (9)
C13—O2—C12—C2	173.30 (9)	C26—C23—C24—O4	−0.51 (13)
C3—C2—C12—O3	133.10 (11)	C27—O5—C26—O6	−0.75 (16)
C1—C2—C12—O3	−42.33 (15)	C27—O5—C26—C23	176.75 (10)
C3—C2—C12—O2	−43.28 (13)	C22—C23—C26—O6	118.12 (12)
C1—C2—C12—O2	141.29 (9)	C24—C23—C26—O6	−61.09 (14)
C1—C10—C14—C15	−113.78 (10)	C22—C23—C26—O5	−59.33 (12)
C9—C10—C14—C15	65.48 (12)	C24—C23—C26—O5	121.46 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O4	0.95	2.19	3.0871 (13)	158
C11—H11A···O3	0.98	2.47	3.1107 (15)	123
C14—H14A···O1	0.99	2.42	2.8830 (13)	108
C14—H14B···O4	0.99	2.41	2.8768 (12)	108
C17—H17···O1	0.95	2.31	3.2206 (13)	161
C19—H19···O3ⁱ	0.95	2.58	3.2069 (14)	124
C22—H22···O6ⁱⁱ	0.95	2.53	3.4172 (13)	156
C25—H25A···O6	0.98	2.49	3.1471 (15)	124
C5—H5···Cg2ⁱⁱⁱ	0.95	2.82	3.6488 (12)	146
C11—H11B···Cg2^iv	0.98	2.78	3.5780 (13)	139

Symmetry codes: (i) −x, −y+1, −z; (ii) x, −y+3/2, z−1/2; (iii) −x+1, −y+1, −z+1; (iv) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₄O₆
M_r	444.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	153
a, b, c (Å)	12.9871 (4), 20.0999 (5), 8.7466 (3)
β (°)	106.798 (1)
V (Å³)	2185.78 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.59 × 0.58 × 0.58

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	21180, 5007, 4617
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.099, 1.01
No. of reflections	5007
No. of parameters	303
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.20

Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), RAPID-AUTO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Bruker, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O4	0.95	2.19	3.0871 (13)	158
C11—H11A···O3	0.98	2.47	3.1107 (15)	123
C14—H14A···O1	0.99	2.42	2.8830 (13)	108
C14—H14B···O4	0.99	2.41	2.8768 (12)	108
C17—H17···O1	0.95	2.31	3.2206 (13)	161
C19—H19···O3ⁱ	0.95	2.58	3.2069 (14)	124
C22—H22···O6ⁱⁱ	0.95	2.53	3.4172 (13)	156
C25—H25A···O6	0.98	2.49	3.1471 (15)	124
C5—H5···Cg2ⁱⁱⁱ	0.95	2.82	3.6488 (12)	146
C11—H11B···Cg2^iv	0.98	2.78	3.5780 (13)	139

Symmetry codes: (i) −x, −y+1, −z; (ii) x, −y+3/2, z−1/2; (iii) −x+1, −y+1, −z+1; (iv) −x, −y+1, −z+1.

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