(R)-2-Benzyl-4-methyl­pentyl (R)-2-meth­oxy-2-(1-naphth­yl)propionate

Inoue, Y.; Matsumoto, T.; Watanabe, M.; Katagiri, H.; Kumagai, T.

doi:10.1107/S160053681002101X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1665

doi:10.1107/S160053681002101X

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(R)-2-Benzyl-4-methylpentyl (R)-2-methoxy-2-(1-naphthyl)propionate

Yoshinori Inoue,^a ^* Takatoshi Matsumoto,^b Masataka Watanabe,^a Hiroshi Katagiri ^c and Tsutomu Kumagai ^a

^aDepartment of Material Science, School of Engineering, The University of Shiga Prefecture, 2500 Hassaka-cho, Hikone, Shiga 522-8533, Japan, ^bInstitute of Multidisciplinary Research for Advanced Materials, Tohoku University, 2-2-1 Katahira, Aoba, Sendai 980-8577, Japan, and ^cDepartment of Chemistry and Chemical Engineering, Graduate School of Science and Engineering, Yamagata University, 4-3-16 Jonan, Yonezawa, Yamagata 992-8510, Japan
^*Correspondence e-mail: inoue@mat.usp.ac.jp

(Received 21 May 2010; accepted 2 June 2010; online 16 June 2010)

The relative configuration of the alcohol component in the title ester, C₂₇H₃₂O₃, has been assigned as (R) from the known configuration of (R)-(−)-2-methoxy-2-(1-naphthyl)propionic acid [(R)-MαNP acid]. In the crystal structure, the C atom of the methyl group of the MαNP acid lies in the extended plane of the naphthyl ring system [methyl C atom deviates from plane by 0.211 (2) Å; r.m.s. deviation of fitted atoms = 0.0187 Å] and a weak intramolecular C—H⋯O hydrogen bond links the naphthyl ring system and the methoxy group. These structural properties are similar to those of most MαNP acid esters.

Related literature

For general background to the crystalline-state analysis of 2-methoxy-2-(1-naphthyl)propionic acid esters, see: Kuwahara et al. (2007 ); Sekiguchi et al. (2008 ).

Experimental

Crystal data

C₂₇H₃₂O₃
M_r = 404.53
Monoclinic, P 2₁
a = 9.3380 (1) Å
b = 12.4142 (1) Å
c = 10.0317 (5) Å
β = 102.8144 (8)°
V = 1133.95 (6) Å³
Z = 2
Cu Kα radiation
μ = 0.59 mm⁻¹
T = 105 K
0.60 × 0.60 × 0.60 mm

Data collection

Rigaku R-AXIS RAPID CCD diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.896, T_max = 1.000
21388 measured reflections
4133 independent reflections
4042 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.068
S = 1.06
4133 reflections
276 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.11 e Å⁻³
Absolute structure: Flack (1983 ), 1592 Friedel pairs
Flack parameter: 0.03 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1	0.95	2.40	2.9887 (15)	120

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2003 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: Yadokari-XG 2009 (Wakita, 2001 ; Kabuto et al. (2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681002101X/zs2041sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681002101X/zs2041Isup2.hkl

checkCIF report

Comment top

In a previous paper, we reported that (S)-2-methoxy-2-(1-naphthyl)propionic acid [(S)-MαNP acid] is an efficient auxiliary for enantioresolution of racemic secondary alcohols and the simultaneous determination of the absolute configuration of the resolved alcohols by the Advanced Mosher Method (Kuwahara et al., 2007). We also reported the determination of the absolute configuration of esters condensed with (S)-MαNP acid using X-ray crystallography, by comparison with the known configuration of the asymmetric quaternary carbon of the acid as an internal standard (Sekiguchi et al., 2008). We will report herein that that (R)-MαNP acid is also a useful auxiliary for the identification of remote asymmetric centers in primary alcohols.

2-Isobutyl-3-phenyl-1-propanol was enantioresolved using (R)-(-)-2-methoxy-2-(1-naphthyl)propionic acid and the absolute configuration of the alcohol component of the second fraction from the HPLC separation, the ester C₂₇H₃₂O₃ (I) has (Fig. 1) been assigned as R from the known configuration of (R)-MαNP acid. In the structure of (I) there is a weak intramolecular hydrogen bond linking the naphthyl ring and the methoxy group (C13—H···O1) (Table 1, Fig. 1) which results in the carbon atom of the methyl group lying in the extended plane of the naphthyl ring of the MαNP acid moiety. These structural properties are similar to those of most MαNP acid esters (Kuwahara et al., 2007).

Related literature top

For general background to the crystalline-state analysis of 2-methoxy-2-(1-naphthyl)propionic acid esters, see: Kuwahara et al. (2007); Sekiguchi et al. (2008).

Experimental top

Two diastereomers were obtained from the reaction of (R)-(-)-2-methoxy-2-(1-naphthyl)propionic acid with 2-isobutyl-3-phenyl-1-propanol (Kuwahara et al., 2007) and were separated by HPLC, eluting with a mixture of ethyl acetate and hexane (50:1). After removal of most of the solvent, the residual oil was allowed to stand for 6 months, giving single crystals suitable for X-ray diffraction analysis.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: Yadokari-XG 2009 (Wakita, 2001; Kabuto et al., 2009).

Figures top

Fig. 1. Molecular configuration and atom numbering scheme for the title compound, with displacement ellipsoids drawn at the 50% probability level.

(R)-2-Benzyl-4-methylpentyl (R)-2-methoxy-2-(1-naphthyl)propionate top

Crystal data top

C₂₇H₃₂O₃	F(000) = 436
M_r = 404.53	D_x = 1.185 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: P 2yb	Cell parameters from 21196 reflections
a = 9.3380 (1) Å	θ = 3.6–68.3°
b = 12.4142 (1) Å	µ = 0.59 mm⁻¹
c = 10.0317 (5) Å	T = 105 K
β = 102.8144 (8)°	Prism, colourless
V = 1133.95 (6) Å³	0.60 × 0.60 × 0.60 mm
Z = 2

Data collection top

Rigaku R-AXIS RAPID CCD diffractometer	4133 independent reflections
Radiation source: rotating anode	4042 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 68.2°, θ_min = 4.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→11
T_min = 0.896, T_max = 1.000	k = −14→14
21388 measured reflections	l = −12→11

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.025	w = 1/[σ²(F_o²) + (0.0376P)² + 0.1169P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.068	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.16 e Å⁻³
4133 reflections	Δρ_min = −0.11 e Å⁻³
276 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0049 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1592 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.03 (13)

Crystal data top

C₂₇H₃₂O₃	V = 1133.95 (6) Å³
M_r = 404.53	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 9.3380 (1) Å	µ = 0.59 mm⁻¹
b = 12.4142 (1) Å	T = 105 K
c = 10.0317 (5) Å	0.60 × 0.60 × 0.60 mm
β = 102.8144 (8)°

Data collection top

Rigaku R-AXIS RAPID CCD diffractometer	4133 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4042 reflections with I > 2σ(I)
T_min = 0.896, T_max = 1.000	R_int = 0.026
21388 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	H-atom parameters constrained
wR(F²) = 0.068	Δρ_max = 0.16 e Å⁻³
S = 1.06	Δρ_min = −0.11 e Å⁻³
4133 reflections	Absolute structure: Flack (1983), 1592 Friedel pairs
276 parameters	Absolute structure parameter: 0.03 (13)
1 restraint

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
C1	0.01084 (12)	0.76296 (10)	0.04854 (12)	0.0259 (2)
O1	−0.00374 (10)	0.66650 (7)	−0.03129 (9)	0.0328 (2)
C2	0.01437 (17)	0.67911 (13)	−0.16720 (14)	0.0422 (3)
H2	−0.0560	0.7325	−0.2148	0.063*
H2A	−0.0030	0.6100	−0.2152	0.063*
H2B	0.1146	0.7035	−0.1654	0.063*
C3	−0.12601 (13)	0.83375 (11)	0.00029 (13)	0.0316 (3)
H3	−0.1275	0.8614	−0.0915	0.047*
H3A	−0.1232	0.8943	0.0636	0.047*
H3B	−0.2145	0.7907	−0.0019	0.047*
C4	0.00305 (11)	0.72333 (10)	0.19225 (12)	0.0246 (2)
O2	−0.05044 (9)	0.63985 (7)	0.21644 (9)	0.0328 (2)
O3	0.05702 (9)	0.79770 (7)	0.28601 (8)	0.02774 (18)
C5	0.15589 (12)	0.82122 (9)	0.05218 (11)	0.0239 (2)
C6	0.15720 (13)	0.92718 (10)	0.01434 (12)	0.0278 (3)
H6	0.0666	0.9633	−0.0185	0.033*
C7	0.28968 (14)	0.98387 (10)	0.02292 (12)	0.0311 (3)
H7	0.2874	1.0570	−0.0053	0.037*
C8	0.42086 (13)	0.93434 (10)	0.07136 (12)	0.0311 (3)
H8	0.5097	0.9734	0.0782	0.037*
C9	0.42564 (12)	0.82428 (10)	0.11183 (11)	0.0267 (3)
C10	0.56161 (13)	0.77226 (11)	0.16393 (12)	0.0319 (3)
H10	0.6503	0.8121	0.1744	0.038*
C11	0.56744 (14)	0.66583 (12)	0.19930 (13)	0.0360 (3)
H11	0.6595	0.6318	0.2330	0.043*
C12	0.43639 (14)	0.60689 (11)	0.18546 (13)	0.0358 (3)
H12	0.4404	0.5327	0.2093	0.043*
C13	0.30273 (13)	0.65541 (10)	0.13778 (12)	0.0295 (3)
H13	0.2154	0.6144	0.1301	0.035*
C14	0.29272 (12)	0.76583 (10)	0.09975 (11)	0.0246 (2)
C15	0.05451 (13)	0.77178 (9)	0.42690 (12)	0.0255 (2)
H15	0.1298	0.7168	0.4632	0.031*
H15A	−0.0429	0.7430	0.4323	0.031*
C16	0.08635 (12)	0.87537 (10)	0.50914 (12)	0.0266 (2)
H16	0.0802	0.8585	0.6052	0.032*
C17	−0.02740 (14)	0.96247 (10)	0.45622 (12)	0.0310 (3)
H17	−0.0271	0.9766	0.3591	0.037*
H17A	0.0037	1.0297	0.5077	0.037*
C18	−0.18533 (14)	0.93703 (11)	0.46642 (14)	0.0355 (3)
H18	−0.2086	0.8617	0.4333	0.043*
C19	−0.29213 (18)	1.01300 (13)	0.37436 (19)	0.0569 (5)
H19	−0.3930	0.9941	0.3782	0.085*
H19A	−0.2803	1.0063	0.2801	0.085*
H19B	−0.2717	1.0873	0.4057	0.085*
C20	−0.20296 (16)	0.94390 (14)	0.61282 (16)	0.0480 (4)
H20	−0.1823	1.0176	0.6467	0.072*
H20A	−0.1342	0.8941	0.6700	0.072*
H20B	−0.3038	0.9245	0.6164	0.072*
C21	0.24294 (14)	0.91710 (10)	0.51362 (13)	0.0313 (3)
H21	0.2519	0.9334	0.4192	0.038*
H21A	0.2576	0.9853	0.5661	0.038*
C22	0.36296 (13)	0.83929 (10)	0.57695 (12)	0.0292 (3)
C23	0.44401 (13)	0.78389 (11)	0.49766 (13)	0.0330 (3)
H23	0.4243	0.7959	0.4018	0.040*
C24	0.55244 (14)	0.71188 (12)	0.55646 (13)	0.0369 (3)
H24	0.6070	0.6754	0.5008	0.044*
C25	0.58239 (14)	0.69240 (11)	0.69620 (14)	0.0360 (3)
H25	0.6571	0.6429	0.7365	0.043*
C26	0.50175 (13)	0.74623 (12)	0.77605 (13)	0.0366 (3)
H26	0.5208	0.7333	0.8717	0.044*
C27	0.39359 (13)	0.81877 (11)	0.71708 (13)	0.0331 (3)
H27	0.3393	0.8552	0.7730	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0258 (5)	0.0274 (6)	0.0248 (6)	−0.0014 (5)	0.0062 (4)	−0.0059 (5)
O1	0.0376 (5)	0.0321 (5)	0.0302 (4)	−0.0074 (4)	0.0108 (4)	−0.0110 (4)
C2	0.0490 (8)	0.0486 (8)	0.0309 (7)	−0.0055 (6)	0.0133 (6)	−0.0142 (6)
C3	0.0240 (5)	0.0424 (7)	0.0278 (6)	0.0023 (5)	0.0042 (5)	−0.0010 (5)
C4	0.0183 (5)	0.0259 (6)	0.0297 (6)	−0.0001 (4)	0.0056 (4)	−0.0041 (5)
O2	0.0344 (4)	0.0293 (5)	0.0350 (5)	−0.0086 (4)	0.0086 (4)	−0.0035 (4)
O3	0.0350 (4)	0.0253 (4)	0.0245 (4)	−0.0067 (3)	0.0099 (3)	−0.0035 (3)
C5	0.0259 (6)	0.0273 (6)	0.0190 (5)	−0.0003 (4)	0.0065 (4)	−0.0029 (4)
C6	0.0309 (6)	0.0279 (6)	0.0246 (6)	0.0035 (5)	0.0062 (5)	0.0003 (5)
C7	0.0405 (7)	0.0279 (6)	0.0250 (6)	−0.0039 (5)	0.0077 (5)	0.0026 (5)
C8	0.0337 (6)	0.0373 (7)	0.0237 (6)	−0.0115 (5)	0.0090 (5)	−0.0016 (5)
C9	0.0283 (6)	0.0364 (7)	0.0168 (5)	−0.0007 (5)	0.0080 (4)	−0.0012 (5)
C10	0.0244 (5)	0.0497 (8)	0.0228 (6)	−0.0002 (5)	0.0080 (4)	−0.0022 (5)
C11	0.0302 (6)	0.0520 (9)	0.0270 (6)	0.0153 (6)	0.0092 (5)	0.0027 (6)
C12	0.0407 (7)	0.0352 (7)	0.0346 (7)	0.0129 (6)	0.0149 (5)	0.0034 (6)
C13	0.0317 (6)	0.0283 (7)	0.0311 (6)	0.0030 (5)	0.0125 (5)	−0.0002 (5)
C14	0.0268 (6)	0.0284 (6)	0.0201 (5)	0.0017 (4)	0.0082 (4)	−0.0013 (4)
C15	0.0281 (5)	0.0250 (6)	0.0244 (5)	−0.0007 (5)	0.0082 (4)	0.0026 (4)
C16	0.0303 (6)	0.0271 (6)	0.0234 (6)	−0.0007 (5)	0.0079 (4)	0.0003 (5)
C17	0.0425 (7)	0.0249 (6)	0.0249 (6)	0.0024 (5)	0.0061 (5)	−0.0003 (5)
C18	0.0333 (6)	0.0297 (7)	0.0388 (7)	0.0038 (5)	−0.0023 (5)	−0.0079 (6)
C19	0.0455 (9)	0.0390 (9)	0.0714 (11)	0.0092 (7)	−0.0189 (8)	−0.0095 (8)
C20	0.0368 (7)	0.0573 (10)	0.0536 (9)	−0.0032 (7)	0.0178 (6)	−0.0117 (7)
C21	0.0355 (6)	0.0289 (6)	0.0302 (6)	−0.0072 (5)	0.0090 (5)	−0.0029 (5)
C22	0.0274 (6)	0.0320 (6)	0.0276 (6)	−0.0092 (5)	0.0051 (5)	−0.0030 (5)
C23	0.0317 (6)	0.0418 (7)	0.0261 (6)	−0.0055 (6)	0.0077 (5)	−0.0012 (5)
C24	0.0309 (6)	0.0457 (8)	0.0355 (7)	−0.0030 (6)	0.0102 (5)	−0.0037 (6)
C25	0.0267 (6)	0.0427 (8)	0.0361 (7)	−0.0025 (5)	0.0016 (5)	0.0012 (6)
C26	0.0314 (6)	0.0501 (9)	0.0252 (6)	−0.0082 (6)	−0.0001 (5)	−0.0026 (6)
C27	0.0304 (6)	0.0421 (8)	0.0269 (6)	−0.0096 (5)	0.0065 (5)	−0.0104 (5)

Geometric parameters (Å, º) top

C1—O1	1.4303 (14)	C15—C16	1.5211 (16)
C1—C5	1.5288 (15)	C15—H15	0.9900
C1—C3	1.5379 (16)	C15—H15A	0.9900
C1—C4	1.5402 (16)	C16—C17	1.5262 (16)
O1—C2	1.4192 (16)	C16—C21	1.5426 (16)
C2—H2	0.9800	C16—H16	1.0000
C2—H2A	0.9800	C17—C18	1.5337 (18)
C2—H2B	0.9800	C17—H17	0.9900
C3—H3	0.9800	C17—H17A	0.9900
C3—H3A	0.9800	C18—C20	1.516 (2)
C3—H3B	0.9800	C18—C19	1.5258 (19)
C4—O2	1.1984 (14)	C18—H18	1.0000
C4—O3	1.3344 (14)	C19—H19	0.9800
O3—C15	1.4548 (13)	C19—H19A	0.9800
C5—C6	1.3700 (17)	C19—H19B	0.9800
C5—C14	1.4361 (15)	C20—H20	0.9800
C6—C7	1.4092 (17)	C20—H20A	0.9800
C6—H6	0.9500	C20—H20B	0.9800
C7—C8	1.3604 (18)	C21—C22	1.5089 (18)
C7—H7	0.9500	C21—H21	0.9900
C8—C9	1.4233 (18)	C21—H21A	0.9900
C8—H8	0.9500	C22—C27	1.3944 (17)
C9—C10	1.4169 (17)	C22—C23	1.3949 (18)
C9—C14	1.4196 (16)	C23—C24	1.3811 (19)
C10—C11	1.3660 (19)	C23—H23	0.9500
C10—H10	0.9500	C24—C25	1.3885 (19)
C11—C12	1.406 (2)	C24—H24	0.9500
C11—H11	0.9500	C25—C26	1.387 (2)
C12—C13	1.3728 (17)	C25—H25	0.9500
C12—H12	0.9500	C26—C27	1.384 (2)
C13—C14	1.4204 (17)	C26—H26	0.9500
C13—H13	0.9500	C27—H27	0.9500

O1—C1—C5	112.53 (9)	C16—C15—H15A	110.3
O1—C1—C3	109.45 (9)	H15—C15—H15A	108.5
C5—C1—C3	114.03 (10)	C15—C16—C17	111.91 (9)
O1—C1—C4	103.79 (9)	C15—C16—C21	111.70 (9)
C5—C1—C4	110.75 (9)	C17—C16—C21	110.75 (10)
C3—C1—C4	105.59 (9)	C15—C16—H16	107.4
C2—O1—C1	115.39 (10)	C17—C16—H16	107.4
O1—C2—H2	109.5	C21—C16—H16	107.4
O1—C2—H2A	109.5	C16—C17—C18	115.86 (10)
H2—C2—H2A	109.5	C16—C17—H17	108.3
O1—C2—H2B	109.5	C18—C17—H17	108.3
H2—C2—H2B	109.5	C16—C17—H17A	108.3
H2A—C2—H2B	109.5	C18—C17—H17A	108.3
C1—C3—H3	109.5	H17—C17—H17A	107.4
C1—C3—H3A	109.5	C20—C18—C19	110.78 (13)
H3—C3—H3A	109.5	C20—C18—C17	111.45 (11)
C1—C3—H3B	109.5	C19—C18—C17	109.96 (12)
H3—C3—H3B	109.5	C20—C18—H18	108.2
H3A—C3—H3B	109.5	C19—C18—H18	108.2
O2—C4—O3	124.39 (11)	C17—C18—H18	108.2
O2—C4—C1	125.03 (10)	C18—C19—H19	109.5
O3—C4—C1	110.48 (9)	C18—C19—H19A	109.5
C4—O3—C15	116.54 (9)	H19—C19—H19A	109.5
C6—C5—C14	119.33 (10)	C18—C19—H19B	109.5
C6—C5—C1	120.66 (10)	H19—C19—H19B	109.5
C14—C5—C1	119.98 (10)	H19A—C19—H19B	109.5
C5—C6—C7	121.62 (11)	C18—C20—H20	109.5
C5—C6—H6	119.2	C18—C20—H20A	109.5
C7—C6—H6	119.2	H20—C20—H20A	109.5
C8—C7—C6	120.32 (11)	C18—C20—H20B	109.5
C8—C7—H7	119.8	H20—C20—H20B	109.5
C6—C7—H7	119.8	H20A—C20—H20B	109.5
C7—C8—C9	120.31 (11)	C22—C21—C16	114.08 (10)
C7—C8—H8	119.8	C22—C21—H21	108.7
C9—C8—H8	119.8	C16—C21—H21	108.7
C10—C9—C14	119.58 (11)	C22—C21—H21A	108.7
C10—C9—C8	120.77 (11)	C16—C21—H21A	108.7
C14—C9—C8	119.65 (11)	H21—C21—H21A	107.6
C11—C10—C9	121.16 (12)	C27—C22—C23	117.96 (12)
C11—C10—H10	119.4	C27—C22—C21	120.57 (11)
C9—C10—H10	119.4	C23—C22—C21	121.45 (11)
C10—C11—C12	119.61 (12)	C24—C23—C22	120.98 (12)
C10—C11—H11	120.2	C24—C23—H23	119.5
C12—C11—H11	120.2	C22—C23—H23	119.5
C13—C12—C11	120.68 (13)	C23—C24—C25	120.55 (12)
C13—C12—H12	119.7	C23—C24—H24	119.7
C11—C12—H12	119.7	C25—C24—H24	119.7
C12—C13—C14	121.17 (12)	C26—C25—C24	119.06 (13)
C12—C13—H13	119.4	C26—C25—H25	120.5
C14—C13—H13	119.4	C24—C25—H25	120.5
C9—C14—C13	117.78 (10)	C27—C26—C25	120.33 (12)
C9—C14—C5	118.70 (10)	C27—C26—H26	119.8
C13—C14—C5	123.50 (10)	C25—C26—H26	119.8
O3—C15—C16	107.26 (9)	C26—C27—C22	121.11 (12)
O3—C15—H15	110.3	C26—C27—H27	119.4
C16—C15—H15	110.3	C22—C27—H27	119.4
O3—C15—H15A	110.3

C5—C1—O1—C2	−54.27 (13)	C8—C9—C14—C13	178.30 (10)
C3—C1—O1—C2	73.61 (13)	C10—C9—C14—C5	177.39 (10)
C4—C1—O1—C2	−174.05 (10)	C8—C9—C14—C5	−2.68 (16)
O1—C1—C4—O2	−21.54 (14)	C12—C13—C14—C9	0.39 (16)
C5—C1—C4—O2	−142.53 (11)	C12—C13—C14—C5	−178.57 (11)
C3—C1—C4—O2	93.57 (13)	C6—C5—C14—C9	2.77 (16)
O1—C1—C4—O3	161.89 (8)	C1—C5—C14—C9	−175.26 (9)
C5—C1—C4—O3	40.90 (12)	C6—C5—C14—C13	−178.28 (11)
C3—C1—C4—O3	−83.00 (11)	C1—C5—C14—C13	3.69 (17)
O2—C4—O3—C15	2.47 (16)	C4—O3—C15—C16	−166.99 (9)
C1—C4—O3—C15	179.06 (9)	O3—C15—C16—C17	59.82 (12)
O1—C1—C5—C6	125.29 (11)	O3—C15—C16—C21	−64.99 (12)
C3—C1—C5—C6	−0.14 (15)	C15—C16—C17—C18	63.25 (13)
C4—C1—C5—C6	−119.05 (11)	C21—C16—C17—C18	−171.41 (10)
O1—C1—C5—C14	−56.71 (13)	C16—C17—C18—C20	73.35 (14)
C3—C1—C5—C14	177.87 (10)	C16—C17—C18—C19	−163.40 (11)
C4—C1—C5—C14	58.95 (13)	C15—C16—C21—C22	−59.85 (13)
C14—C5—C6—C7	−1.01 (17)	C17—C16—C21—C22	174.69 (10)
C1—C5—C6—C7	177.01 (10)	C16—C21—C22—C27	−70.82 (14)
C5—C6—C7—C8	−0.91 (18)	C16—C21—C22—C23	107.61 (13)
C6—C7—C8—C9	0.99 (17)	C27—C22—C23—C24	−0.76 (18)
C7—C8—C9—C10	−179.25 (11)	C21—C22—C23—C24	−179.22 (12)
C7—C8—C9—C14	0.82 (16)	C22—C23—C24—C25	0.5 (2)
C14—C9—C10—C11	1.84 (17)	C23—C24—C25—C26	0.1 (2)
C8—C9—C10—C11	−178.08 (11)	C24—C25—C26—C27	−0.4 (2)
C9—C10—C11—C12	−0.77 (18)	C25—C26—C27—C22	0.12 (19)
C10—C11—C12—C13	−0.50 (19)	C23—C22—C27—C26	0.44 (18)
C11—C12—C13—C14	0.68 (18)	C21—C22—C27—C26	178.92 (11)
C10—C9—C14—C13	−1.62 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.95	2.40	2.9887 (15)	120

Experimental details

Crystal data
Chemical formula	C₂₇H₃₂O₃
M_r	404.53
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	105
a, b, c (Å)	9.3380 (1), 12.4142 (1), 10.0317 (5)
β (°)	102.8144 (8)
V (Å³)	1133.95 (6)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.60 × 0.60 × 0.60

Data collection
Diffractometer	Rigaku R-AXIS RAPID CCD diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.896, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	21388, 4133, 4042
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.068, 1.06
No. of reflections	4133
No. of parameters	276
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.11
Absolute structure	Flack (1983), 1592 Friedel pairs
Absolute structure parameter	0.03 (13)

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), Yadokari-XG 2009 (Wakita, 2001; Kabuto et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.95	2.40	2.9887 (15)	120

References

Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Kabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009). J. Cryst. Soc. Jpn, 51, 218–224. CrossRef Google Scholar
Kuwahara, S., Naito, J., Yamamoto, Y., Kasai, Y., Fujita, T., Noro, K., Shimanuki, K., Akagi, M., Watanabe, M., Matsumoto, T., Watanabe, M., Ichikawa, A. & Harada, N. (2007). Eur. J. Org. Chem. 11, 1827–1840. CSD CrossRef Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2003). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sekiguchi, S., Akagi, M., Naito, J., Yamamoto, Y., Taji, H., Kuwahara, S., Watanabe, M., Ozawa, Y., Toriumi, K. & Harada, N. (2008). Eur. J. Org. Chem. 13, 2313–2324. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wakita, K. (2001). Yadokari-XG. Department of Chemistry, Graduate School of Science, The University of Tokyo, Japan. Google Scholar

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Volume 66| Part 7| July 2010| Page o1665

doi:10.1107/S160053681002101X

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