(1R,2S)-[(R)-1-(2-Hy­droxy­naphthalen-1-yl)naphthalen-2-yl] 2-ethynyl­cyclo­propane-1-carboxyl­ate

Fan, J.L.; Qin, Z.H.

doi:10.1107/S1600536811011627

organic compounds

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Volume 67| Part 6| June 2011| Page o1342

doi:10.1107/S1600536811011627

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(1R,2S)-[(R)-1-(2-Hydroxynaphthalen-1-yl)naphthalen-2-yl] 2-ethynylcyclopropane-1-carboxylate

Jinlong Fan ^a and Zhaohai Qin ^a ^*

^aCollege of Science, China Agricultural University, 100094 Beijing, People's Republic of China
^*Correspondence e-mail: qinzhaohai@263.net

(Received 1 November 2010; accepted 29 March 2011; online 7 May 2011)

In the crystal structure of the title compound, C₂₆H₁₈O₃, molecules with stereochemistry (1R,2S,R), are connected by O—H⋯O hydrogen bonds, forming chains.

Related literature

The title structure is a stable cyclopropane formate ester intermediate in the synthesis of abscisic acid analogues. (1S)-(+)-Abscisic acid is an important phytohormone with many functions in higher plants including roles in seed germination, development and dormancy, regulating the stomatal movements and improving stress tolerance, see: Frey et al. (1999 ); Jiang & Zhang (2004 ). For the synthesis of cyclopropane formate ester, see: Reichelt & Martin (2006 ); Boche & Lohrenz (2001 ); Lebel et al. (2003 ); Molander & Etter (1987 ).

Experimental

Crystal data

C₂₆H₁₈O₃
M_r = 378.40
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.0376 (11) Å
b = 12.0600 (17) Å
c = 20.324 (3) Å
V = 1970.1 (5) Å³
Z = 4
Cu Kα radiation
μ = 0.66 mm⁻¹
T = 173 K
0.65 × 0.48 × 0.35 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 2001 ) T_min = 0.673, T_max = 0.801
13939 measured reflections
3554 independent reflections
3391 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.074
S = 1.07
3554 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.13 e Å⁻³
Absolute structure: Flack (1983 ), 1471 Friedel pairs
Flack parameter: −0.06 (19)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O3ⁱ	0.84	2.01	2.8520 (16)	177
Symmetry code: (i) x+1, y, z.

Data collection: RAPID-AUTO (Rigaku 1998 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011627/gw2095sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811011627/gw2095Isup2.hkl

checkCIF report

Comment top

(1S)-(+)-Abscisic acid (ABA) is an important phytohormone with many functions in higher plants including roles in seed germination, development and dormancy, regulating the stomatal movements and improving stress tolerance (Frey et al., 1999; Jiang et al., 2004). The title structure, C₂₆H₁₈O₃, is a stable cyclopropane formate ester intermediate in the synthesis of Abscisic acid analoge. During the course of our study, we remove the protected group, trimethanesilicon, from the compound of (1R,2S)-((R)-2'-hydroxy-1,1'-binaphthyl-2-yl) 2-((trimethylsilyl)ethynyl)cyclopropanecarboxylate, to obtain the title compoud. In this paper, we reported crystal structure of the title compound.

The crystal structure is shown in Figure1. The crystal structure consists of one three-membered rings(A) and two naphthalene nucleus(B/C). The C22 is R configuration with the dihedral angles C22—C23—C24—C25 = 109.07 (51)°. The C24 is S configuration with the dihedral angles C21—C22—C24—C23 = 108.01 (53)°. The two naphthalene nucleus(B/C) is R configuration with the dihedral angles C(1)—C(10)—C(11)—C(20) = 92.85 (07)°. the compounds are connected by O1—H1A···O3i,hydrogen bonds (2.852, Symmetry code: (i) x + 1, y, z.).

Related literature top

The title structure is a stable cyclopropane formate ester intermediate in the synthesis of abscisic acid analogues. (1S)-(+)-Abscisic acid is an important phytohormone with many functions in higher plants including roles in seed germination, development and dormancy, regulating the stomatal movements and improving stress tolerance, see: Frey et al. (1999); Jiang & Zhang (2004). For the synthesis of cyclopropane formate ester, see: Reichelt & Martin (2006); Boche & Lohrenz (2001); Lebel et al. (2003); Molander & Etter (1987).

Experimental top

A solution of (1R,2S)-((R)-2'-hydroxy-1,1'-binaphthyl-2-yl) 2-((trimethylsilyl)ethynyl)cyclopropanecarboxylate (360 mg, 0.775 mmol) was cooled to 0 ^°C, and TBAF (1.0 M THF solution, 1.16 ml, 1.16 mmol) was added. The resulting solution was stirred for 3 h at 0^°C. Saturated NH4Cl solution was added, and the aqueous phase was extracted with Et₂O. The organic phase was washed with brine, dried over Na₂SO₄, filtered, and concentrated. The residue was purified by column chromatography on silica gel (1:1 hexane/benzene) to provide 23a (229.4 mg, 78.3%). 1H NMR (500 MHz, CDCl₃,TMS): δ 0.9566–1.1.0282 (m,1H), 1.0925 - 1.1524(m, 1H), 1.6355–1.7887 (m, 2 H), 1.9454–1.9527 (d, 1 H), 5.3893 (s, 1 H), 7.0617–7.0659(q,1 H), 7.2167–7.3231 (m, 6H), 7.4202–7.4686(q, 2 H), 7.8104–7.9397 (ddd,3H), 8.0015–8.0309(d, 1 H); 13 C NMR (75 MHz, CDCl₃): δ10.027, 14.828, 20.324, 29.639, 68.373, 80.191, 114.146, 118.643, 121.931, 123.372, 124.595, 125.744, 126.186, 126.542, 127.313, 127.910, 128.984, 130.116, 130.545, 132.182, 133.450, 133.577. The compound was redissolved in n-hexane (20 ml) and dichloromethane (5 ml), and crystals suitable for X-ray analysis were grown from slow evaporation of the solvent at room temperature.

Computing details top

Data collection: RAPID-AUTO (Rigaku 1998); cell refinement: RAPID-AUTO (Rigaku 1998); data reduction: RAPID-AUTO (Rigaku 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Ellipsoid plot.
	Fig. 2. Packing diagram.

(1R,2S)-[(R)-1-(2-hydroxynaphthalen-1-yl)naphthalen-2-yl] 2-ethynylcyclopropane-1-carboxylate top

Crystal data top

C₂₆H₁₈O₃	F(000) = 792
M_r = 378.40	D_x = 1.276 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54186 Å
Hall symbol: P 2ac 2ab	Cell parameters from 14013 reflections
a = 8.0376 (11) Å	θ = 3.1–68.2°
b = 12.0600 (17) Å	µ = 0.66 mm⁻¹
c = 20.324 (3) Å	T = 173 K
V = 1970.1 (5) Å³	Block, colorless
Z = 4	0.65 × 0.48 × 0.35 mm

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	3554 independent reflections
Radiation source: rotating anode	3391 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 68.2°, θ_min = 4.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 2001)	h = −9→9
T_min = 0.673, T_max = 0.801	k = −12→14
13939 measured reflections	l = −24→24

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)] = 0.032	H-atom parameters constrained
wR(F²) = 0.074	w = 1/[σ²(F_o²) + (0.0274P)² + 0.3717P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
3554 reflections	Δρ_max = 0.11 e Å⁻³
262 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1471 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.06 (19)

Crystal data top

C₂₆H₁₈O₃	V = 1970.1 (5) Å³
M_r = 378.40	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 8.0376 (11) Å	µ = 0.66 mm⁻¹
b = 12.0600 (17) Å	T = 173 K
c = 20.324 (3) Å	0.65 × 0.48 × 0.35 mm

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	3554 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 2001)	3391 reflections with I > 2σ(I)
T_min = 0.673, T_max = 0.801	R_int = 0.032
13939 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.074	Δρ_max = 0.11 e Å⁻³
S = 1.07	Δρ_min = −0.13 e Å⁻³
3554 reflections	Absolute structure: Flack (1983), 1471 Friedel pairs
262 parameters	Absolute structure parameter: −0.06 (19)
0 restraints

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	0.82773 (14)	0.36744 (9)	0.81560 (6)	0.0412 (3)
H1A	0.9241	0.3840	0.8030	0.062*
O2	0.41585 (13)	0.38707 (9)	0.74612 (5)	0.0360 (3)
O3	0.15312 (14)	0.43096 (11)	0.77423 (6)	0.0443 (3)
C1	0.75354 (19)	0.45851 (13)	0.84229 (7)	0.0294 (3)
C2	0.84313 (19)	0.55862 (13)	0.85081 (8)	0.0326 (3)
H2A	0.9556	0.5632	0.8367	0.039*
C3	0.7695 (2)	0.64824 (13)	0.87909 (7)	0.0329 (4)
H3A	0.8313	0.7147	0.8847	0.039*
C4	0.6014 (2)	0.64350 (13)	0.90027 (7)	0.0306 (3)
C5	0.5215 (2)	0.73583 (14)	0.92935 (8)	0.0374 (4)
H5A	0.5808	0.8035	0.9340	0.045*
C6	0.3614 (2)	0.72960 (14)	0.95074 (8)	0.0415 (4)
H6A	0.3103	0.7920	0.9709	0.050*
C7	0.2721 (2)	0.63017 (15)	0.94282 (8)	0.0402 (4)
H7A	0.1599	0.6260	0.9573	0.048*
C8	0.3447 (2)	0.53947 (14)	0.91456 (8)	0.0350 (4)
H8A	0.2821	0.4732	0.9097	0.042*
C9	0.51197 (19)	0.54257 (12)	0.89239 (7)	0.0280 (3)
C10	0.59105 (18)	0.44935 (12)	0.86295 (7)	0.0270 (3)
C11	0.50195 (18)	0.34074 (12)	0.85607 (7)	0.0279 (3)
C12	0.4190 (2)	0.31262 (13)	0.79970 (7)	0.0319 (3)
C13	0.3400 (2)	0.21003 (15)	0.79066 (8)	0.0419 (4)
H13A	0.2861	0.1937	0.7502	0.050*
C14	0.3408 (2)	0.13429 (14)	0.83998 (9)	0.0406 (4)
H14A	0.2880	0.0646	0.8338	0.049*
C15	0.4194 (2)	0.15809 (13)	0.90047 (8)	0.0341 (4)
C16	0.4193 (2)	0.08122 (14)	0.95328 (9)	0.0411 (4)
H16A	0.3670	0.0112	0.9477	0.049*
C17	0.4927 (2)	0.10604 (15)	1.01160 (10)	0.0460 (4)
H17A	0.4917	0.0534	1.0463	0.055*
C18	0.5704 (2)	0.20966 (16)	1.02082 (9)	0.0460 (4)
H18A	0.6197	0.2271	1.0620	0.055*
C19	0.5753 (2)	0.28568 (15)	0.97044 (8)	0.0363 (4)
H19A	0.6297	0.3548	0.9770	0.044*
C20	0.50037 (19)	0.26228 (13)	0.90897 (7)	0.0296 (3)
C21	0.2672 (2)	0.43827 (14)	0.73624 (8)	0.0355 (4)
C22	0.2674 (2)	0.49921 (16)	0.67393 (9)	0.0469 (4)
H22A	0.3780	0.5094	0.6522	0.056*
C23	0.1432 (3)	0.59106 (16)	0.66459 (12)	0.0627 (6)
H23A	0.0669	0.6075	0.7016	0.075*
H23B	0.1790	0.6568	0.6391	0.075*
C24	0.1168 (2)	0.48554 (16)	0.62786 (9)	0.0482 (5)
H24A	0.1427	0.4888	0.5798	0.058*
C25	−0.0173 (2)	0.41205 (15)	0.64584 (9)	0.0424 (4)
C26	−0.1269 (3)	0.35242 (17)	0.66089 (10)	0.0527 (5)
H26	−0.2153	0.3043	0.6730	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0302 (6)	0.0372 (6)	0.0561 (7)	−0.0033 (5)	0.0157 (5)	−0.0033 (6)
O2	0.0278 (6)	0.0474 (7)	0.0327 (5)	−0.0075 (5)	0.0028 (5)	0.0014 (5)
O3	0.0312 (6)	0.0593 (8)	0.0424 (6)	−0.0025 (6)	0.0080 (5)	0.0005 (6)
C1	0.0271 (8)	0.0314 (8)	0.0295 (7)	−0.0030 (6)	0.0028 (6)	0.0018 (6)
C2	0.0255 (8)	0.0375 (9)	0.0348 (8)	−0.0076 (7)	−0.0016 (6)	0.0075 (7)
C3	0.0351 (9)	0.0309 (8)	0.0326 (8)	−0.0127 (7)	−0.0058 (7)	0.0051 (7)
C4	0.0351 (9)	0.0284 (8)	0.0283 (7)	−0.0050 (7)	−0.0044 (6)	0.0023 (6)
C5	0.0478 (11)	0.0284 (8)	0.0360 (8)	−0.0054 (7)	−0.0053 (7)	−0.0035 (7)
C6	0.0493 (11)	0.0341 (9)	0.0410 (9)	0.0048 (8)	0.0017 (8)	−0.0082 (8)
C7	0.0348 (9)	0.0434 (10)	0.0426 (9)	0.0005 (8)	0.0057 (7)	−0.0074 (8)
C8	0.0319 (8)	0.0348 (9)	0.0384 (8)	−0.0041 (7)	0.0026 (7)	−0.0075 (7)
C9	0.0282 (7)	0.0293 (8)	0.0265 (7)	−0.0046 (6)	−0.0021 (6)	0.0001 (6)
C10	0.0246 (7)	0.0278 (8)	0.0284 (7)	−0.0051 (6)	−0.0003 (6)	0.0008 (6)
C11	0.0212 (7)	0.0294 (8)	0.0330 (8)	−0.0031 (6)	0.0055 (6)	−0.0057 (6)
C12	0.0268 (8)	0.0353 (8)	0.0336 (8)	−0.0046 (7)	0.0062 (6)	−0.0031 (7)
C13	0.0388 (10)	0.0458 (10)	0.0411 (9)	−0.0132 (8)	0.0013 (7)	−0.0116 (8)
C14	0.0368 (9)	0.0315 (9)	0.0536 (10)	−0.0108 (7)	0.0050 (8)	−0.0121 (8)
C15	0.0264 (8)	0.0299 (8)	0.0458 (9)	0.0004 (7)	0.0098 (7)	−0.0029 (7)
C16	0.0326 (9)	0.0274 (8)	0.0633 (11)	0.0020 (7)	0.0120 (8)	0.0060 (8)
C17	0.0343 (9)	0.0432 (10)	0.0604 (11)	0.0055 (8)	0.0063 (9)	0.0200 (9)
C18	0.0352 (9)	0.0567 (11)	0.0461 (10)	−0.0030 (9)	−0.0038 (8)	0.0114 (9)
C19	0.0289 (8)	0.0394 (9)	0.0405 (9)	−0.0038 (7)	−0.0004 (7)	0.0037 (7)
C20	0.0219 (8)	0.0285 (8)	0.0385 (8)	−0.0010 (6)	0.0056 (6)	−0.0024 (6)
C21	0.0280 (8)	0.0412 (10)	0.0374 (8)	−0.0076 (7)	0.0006 (7)	−0.0033 (7)
C22	0.0373 (10)	0.0528 (11)	0.0505 (10)	−0.0067 (8)	0.0051 (8)	0.0117 (9)
C23	0.0663 (14)	0.0381 (10)	0.0838 (15)	−0.0042 (10)	0.0040 (12)	0.0158 (11)
C24	0.0474 (11)	0.0546 (12)	0.0426 (9)	0.0085 (9)	0.0007 (8)	0.0120 (9)
C25	0.0414 (10)	0.0404 (10)	0.0452 (10)	0.0136 (8)	−0.0111 (8)	−0.0059 (8)
C26	0.0463 (12)	0.0469 (11)	0.0649 (12)	−0.0016 (9)	−0.0109 (9)	−0.0083 (10)

Geometric parameters (Å, º) top

O1—C1	1.3623 (18)	C13—C14	1.356 (2)
O1—H1A	0.8400	C13—H13A	0.9500
O2—C21	1.3596 (19)	C14—C15	1.412 (2)
O2—C12	1.4116 (18)	C14—H14A	0.9500
O3—C21	1.2021 (19)	C15—C16	1.418 (2)
C1—C10	1.376 (2)	C15—C20	1.426 (2)
C1—C2	1.416 (2)	C16—C17	1.357 (3)
C2—C3	1.360 (2)	C16—H16A	0.9500
C2—H2A	0.9500	C17—C18	1.410 (3)
C3—C4	1.419 (2)	C17—H17A	0.9500
C3—H3A	0.9500	C18—C19	1.375 (2)
C4—C5	1.415 (2)	C18—H18A	0.9500
C4—C9	1.423 (2)	C19—C20	1.415 (2)
C5—C6	1.360 (3)	C19—H19A	0.9500
C5—H5A	0.9500	C21—C22	1.464 (2)
C6—C7	1.407 (2)	C22—C23	1.503 (3)
C6—H6A	0.9500	C22—C24	1.539 (3)
C7—C8	1.366 (2)	C22—H22A	1.0000
C7—H7A	0.9500	C23—C24	1.491 (3)
C8—C9	1.418 (2)	C23—H23A	0.9900
C8—H8A	0.9500	C23—H23B	0.9900
C9—C10	1.423 (2)	C24—C25	1.442 (3)
C10—C11	1.4994 (19)	C24—H24A	1.0000
C11—C12	1.368 (2)	C25—C26	1.178 (3)
C11—C20	1.432 (2)	C26—H26	0.9500
C12—C13	1.403 (2)

C1—O1—H1A	109.5	C15—C14—H14A	119.7
C21—O2—C12	114.75 (12)	C14—C15—C16	121.74 (15)
O1—C1—C10	118.17 (13)	C14—C15—C20	119.28 (15)
O1—C1—C2	120.89 (13)	C16—C15—C20	118.98 (15)
C10—C1—C2	120.90 (14)	C17—C16—C15	121.09 (16)
C3—C2—C1	120.53 (14)	C17—C16—H16A	119.5
C3—C2—H2A	119.7	C15—C16—H16A	119.5
C1—C2—H2A	119.7	C16—C17—C18	120.29 (17)
C2—C3—C4	120.70 (14)	C16—C17—H17A	119.9
C2—C3—H3A	119.6	C18—C17—H17A	119.9
C4—C3—H3A	119.6	C19—C18—C17	120.31 (17)
C5—C4—C3	121.82 (15)	C19—C18—H18A	119.8
C5—C4—C9	119.42 (14)	C17—C18—H18A	119.8
C3—C4—C9	118.77 (14)	C18—C19—C20	120.81 (15)
C6—C5—C4	121.29 (15)	C18—C19—H19A	119.6
C6—C5—H5A	119.4	C20—C19—H19A	119.6
C4—C5—H5A	119.4	C19—C20—C15	118.50 (14)
C5—C6—C7	119.55 (16)	C19—C20—C11	121.81 (13)
C5—C6—H6A	120.2	C15—C20—C11	119.69 (14)
C7—C6—H6A	120.2	O3—C21—O2	122.84 (15)
C8—C7—C6	120.84 (16)	O3—C21—C22	126.36 (16)
C8—C7—H7A	119.6	O2—C21—C22	110.79 (14)
C6—C7—H7A	119.6	C21—C22—C23	118.58 (17)
C7—C8—C9	121.15 (15)	C21—C22—C24	118.15 (15)
C7—C8—H8A	119.4	C23—C22—C24	58.66 (13)
C9—C8—H8A	119.4	C21—C22—H22A	116.4
C8—C9—C4	117.75 (14)	C23—C22—H22A	116.4
C8—C9—C10	122.41 (14)	C24—C22—H22A	116.4
C4—C9—C10	119.84 (13)	C24—C23—C22	61.87 (13)
C1—C10—C9	119.25 (13)	C24—C23—H23A	117.6
C1—C10—C11	119.66 (13)	C22—C23—H23A	117.6
C9—C10—C11	121.06 (12)	C24—C23—H23B	117.6
C12—C11—C20	117.42 (13)	C22—C23—H23B	117.6
C12—C11—C10	121.83 (13)	H23A—C23—H23B	114.7
C20—C11—C10	120.75 (13)	C25—C24—C23	120.26 (17)
C11—C12—C13	123.30 (15)	C25—C24—C22	119.94 (15)
C11—C12—O2	119.81 (13)	C23—C24—C22	59.47 (13)
C13—C12—O2	116.85 (14)	C25—C24—H24A	115.3
C14—C13—C12	119.67 (15)	C23—C24—H24A	115.3
C14—C13—H13A	120.2	C22—C24—H24A	115.3
C12—C13—H13A	120.2	C26—C25—C24	179.6 (2)
C13—C14—C15	120.59 (15)	C25—C26—H26	180.0
C13—C14—H14A	119.7

O1—C1—C2—C3	−178.23 (13)	C11—C12—C13—C14	1.5 (3)
C10—C1—C2—C3	−0.6 (2)	O2—C12—C13—C14	179.06 (15)
C1—C2—C3—C4	−0.4 (2)	C12—C13—C14—C15	0.5 (3)
C2—C3—C4—C5	−179.49 (15)	C13—C14—C15—C16	178.77 (16)
C2—C3—C4—C9	1.1 (2)	C13—C14—C15—C20	−0.9 (2)
C3—C4—C5—C6	−178.58 (15)	C14—C15—C16—C17	−178.77 (16)
C9—C4—C5—C6	0.9 (2)	C20—C15—C16—C17	0.9 (2)
C4—C5—C6—C7	−1.1 (2)	C15—C16—C17—C18	0.2 (3)
C5—C6—C7—C8	0.7 (3)	C16—C17—C18—C19	−1.2 (3)
C6—C7—C8—C9	0.0 (3)	C17—C18—C19—C20	1.1 (2)
C7—C8—C9—C4	−0.3 (2)	C18—C19—C20—C15	0.1 (2)
C7—C8—C9—C10	179.83 (15)	C18—C19—C20—C11	179.15 (15)
C5—C4—C9—C8	−0.1 (2)	C14—C15—C20—C19	178.64 (15)
C3—C4—C9—C8	179.33 (14)	C16—C15—C20—C19	−1.1 (2)
C5—C4—C9—C10	179.75 (13)	C14—C15—C20—C11	−0.4 (2)
C3—C4—C9—C10	−0.8 (2)	C16—C15—C20—C11	179.84 (14)
O1—C1—C10—C9	178.55 (13)	C12—C11—C20—C19	−176.82 (15)
C2—C1—C10—C9	0.9 (2)	C10—C11—C20—C19	3.0 (2)
O1—C1—C10—C11	0.4 (2)	C12—C11—C20—C15	2.2 (2)
C2—C1—C10—C11	−177.20 (14)	C10—C11—C20—C15	−177.97 (13)
C8—C9—C10—C1	179.69 (14)	C12—O2—C21—O3	8.2 (2)
C4—C9—C10—C1	−0.2 (2)	C12—O2—C21—C22	−170.69 (13)
C8—C9—C10—C11	−2.2 (2)	O3—C21—C22—C23	22.1 (3)
C4—C9—C10—C11	177.90 (13)	O2—C21—C22—C23	−159.11 (16)
C1—C10—C11—C12	−87.34 (18)	O3—C21—C22—C24	−45.6 (3)
C9—C10—C11—C12	94.59 (18)	O2—C21—C22—C24	133.24 (16)
C1—C10—C11—C20	92.87 (17)	C21—C22—C23—C24	−107.30 (19)
C9—C10—C11—C20	−85.20 (17)	C22—C23—C24—C25	109.08 (18)
C20—C11—C12—C13	−2.8 (2)	C21—C22—C24—C25	−1.6 (3)
C10—C11—C12—C13	177.41 (15)	C23—C22—C24—C25	−109.6 (2)
C20—C11—C12—O2	179.69 (12)	C21—C22—C24—C23	108.0 (2)
C10—C11—C12—O2	−0.1 (2)	C23—C24—C25—C26	−13 (38)
C21—O2—C12—C11	−107.04 (16)	C22—C24—C25—C26	57 (38)
C21—O2—C12—C13	75.28 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3ⁱ	0.84	2.01	2.8520 (16)	177

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₆H₁₈O₃
M_r	378.40
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	8.0376 (11), 12.0600 (17), 20.324 (3)
V (Å³)	1970.1 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.66
Crystal size (mm)	0.65 × 0.48 × 0.35

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 2001)
T_min, T_max	0.673, 0.801
No. of measured, independent and observed [I > 2σ(I)] reflections	13939, 3554, 3391
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.074, 1.07
No. of reflections	3554
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.13
Absolute structure	Flack (1983), 1471 Friedel pairs
Absolute structure parameter	−0.06 (19)

Computer programs: RAPID-AUTO (Rigaku 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3ⁱ	0.84	2.01	2.8520 (16)	177.3

Symmetry code: (i) x+1, y, z.

Acknowledgements

This work was supported by the Natural Science Foundation of China (No. 20972184)

References

Boche, G. & Lohrenz, J. C. W. (2001). Chem. Rev. 101, 697–756. Web of Science CrossRef PubMed CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Frey, A., Audran, C., Marin, E., Sotta, B. & Marion-Poll, A. (1999). Plant Mol. Biol. 39, 1267–1274. Web of Science CrossRef PubMed CAS Google Scholar
Higashi, T. (2001). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Jiang, M. Y. & Zhang, J. H. (2004). Acta Bot. Sin. 46, 1–9. CAS Google Scholar
Lebel, H., Marcoux, J. F., Molinaro, C. & Charette, A. B. (2003). Chem. Rev. 103, 977–1050. Web of Science CrossRef PubMed CAS Google Scholar
Molander, G. A. & Etter, J. B. (1987). J. Org. Chem. 52, 3942–3944. CrossRef CAS Google Scholar
Reichelt, A. & Martin, S. F. (2006). Acc. Chem. Res. 39, 433–442. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 6| June 2011| Page o1342

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(1R,2S)-[(R)-1-(2-Hy­dr­oxy­naphthalen-1-yl)naphthalen-2-yl] 2-ethynyl­cyclo­propane-1-carboxyl­ate

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Experimental

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Refinement

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organic compounds

(1R,2S)-[(R)-1-(2-Hydroxynaphthalen-1-yl)naphthalen-2-yl] 2-ethynylcyclopropane-1-carboxylate