Crystal structure of (1R,4R)-tert-butyl 3-oxo-2-oxa-5-aza­bicyclo­[2.2.2]octane-5-carboxyl­ate

Krishnamurthy, S.; Jalli, V.; Vagvala, T.C.; Moriguchi, T.; Tsuge, A.

doi:10.1107/S2056989015010476

organic compounds

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ISSN: 2056-9890

Volume 71| Part 7| July 2015| Pages o449-o450

doi:10.1107/S2056989015010476

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Crystal structure of (1R,4R)-tert-butyl 3-oxo-2-oxa-5-azabicyclo[2.2.2]octane-5-carboxylate

Suvratha Krishnamurthy,^a ^* Venkataprasad Jalli,^a Tarun Chand Vagvala,^b Tetsuji Moriguchi ^a and Akihiko Tsuge ^a

^aDepartment of Applied Chemistry, Kyushu Institute of Technology, Kitakyushu 804-8550, Japan, and ^bGraduate School of Life Sciences and Systems Engineering, Kyushu Institute of Technology, Kitakyushu 804-8550, Japan
^*Correspondence e-mail: suvrathak@gmail.com

Edited by G. Smith, Queensland University of Technology, Australia (Received 1 May 2015; accepted 1 June 2015; online 6 June 2015)

In the title compound, C₁₁H₁₇NO₄, commonly known as N-tert-butoxycarbonyl-5-hydroxy-D-pipecolic acid lactone, the absolute configuration is (1R,4R) due to the enantiomeric purity of the starting material which remains unchanged during the course of the reaction. In the crystal there no intermolecular hydrogen bonds.

Keywords: crystal structure; (1R,4R)- aza-oxa bicyclic chiral lactone.

CCDC reference: 1062075

1. Related literature

For background information on 5-hydroxypipecolic acid and related compounds, see: Witkop & Foltz (1957 ); Hoarau et al. (1996 ); Sun et al. (2008 ). For the synthesis of a related compound, see: Krishnamurthy et al. (2014 ). For crystal structures of related lactones, see: (1S,4S) conformer, racemic mixture, Moriguchi, Krishnamurthy, Arai & Tsuge (2014 ); Moriguchi, Krishnamurthy, Arai, Matsumoto et al. (2014 ).

2. Experimental

2.1. Crystal data

C₁₁H₁₇NO₄
M_r = 227.26
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.6472 (4) Å
b = 9.7084 (4) Å
c = 12.2323 (5) Å
V = 1145.66 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 90 K
0.45 × 0.40 × 0.40 mm

2.2. Data collection

Bruker APEX2 KY CCD diffractometer
Absorption correction: multi-scan SADABS (Bruker, 2009 ) T_min = 0.870, T_max = 0.961
13518 measured reflections
2791 independent reflections
2728 reflections with I > 2σ(I)
R_int = 0.021

2.3. Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.081
S = 1.03
2791 reflections
148 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.27 e Å⁻³
Absolute structure: Flack (1983 ), 2933 Friedel pairs
Absolute structure parameter: 0.1 (7)

Data collection: APEX2 (Bruker,2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1062075

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015010476/zs2333sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015010476/zs2333Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015010476/zs2333Isup3.cml

checkCIF report

Comment top

5-Hydroxypipecolic acid is a higher homologue of 4-hydroxyproline, which is found in dates (Witkop & Foltz, 1957). 4-Hydroxyproline is formed by post-translational modification of proline in collagen and is responsible for enhancing its stability. Literature reports the synthesis of 5-hydroxypipecolic acid derivatives (Hoarau et al., 1996; Sun et al., 2008), generally forming diastereomeric mixtures of cis- and trans-5-hydroxypipecolic acids. Therefore such syntheses suffer from disadvantages of separation of the diasteromers making the procedure very tedious. A facile procedure to isolate this amino acid was desirable.

Our previous communication reported the synthesis of a 4-hydroxyproline derivative from an amino acid bearing epoxide (Krishnamurthy et al. 2014). It is reported in this study that the cis-isomer undergoes intramolecular lactonization to tert-butyl- 3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate, making the isolation from the trans ester highly feasible. Based on this observation it can be expected that cis-5-hydroxypipecolic acids would also undergo in situ intramolecular lactonization. In fact, when a mixture of a cis- and trans-5-hydroxypipecolic acid derivatives was reacted under acidic conditions, the cis-isomer successfully converted to the lactone (I), subsequently readily separated from the remaining trans--isomer. We had previously reported the crystal structure of racemic tert-butyl- 3-oxo-2-oxa-5-azabicyclo[2.2.2]octane-5-carboxylate (Moriguchi, Krishnamurthy, Arai, Tsuge et al., 2014) and (1S,4S)-tert-butyl 3-oxo-2-oxa-5-azabicyclo[2.2.2]octane-5-carboxylate (Moriguchi, Krishnamurthy, Arai, & Tsuge, 2014). Herein we would like to report the crystal structure of enantiomerically pure (1R,4R)-tert-butyl- 3-oxo-2-oxa-5-azabicyclo[2.2.2]octane-5-carboxylate, C₁₁H₁₇N O₄, (I).

The title compound (I), commonly known as N-tert- butoxycarbonyl-5-hydroxy-D-pipecolic acid lactone, was derived from a starting product having a cis configuration for both hydroxyl and carboxyl groups, leading to lactone formation (Fig. 1). The nitrogen atom N1 appears next to the bridge-head atom within the bicyclic ring system. The absolute configuration of the compound was found to be (1R,4R) due to the configuration of the starting material (Fig. 3). The Flack structure parameter (Flack, 1983) determined for (I) [0.1 (7)], although not definitive because of the uncertainty factor, is considered to provide adequate supporting evidence for this configuration. The desired hydrophobic conformer (1R,4R), (I) was easily isolated from hydrophylic (1R,4S)–(4) (Fig. 3). The intramolecular lactonization is possible only in (1R,4R)–(3) isomer due to its configuration. The hydroxyl and the carboxyl groups are in close proximity due to the cis- configuration of (1R,4R)–(3), which leads to the intamolecular lactonization with loss of EtOH. With the (1R,4S)–(4) isomer the hydroxyl and the carboxyl groups are far apart due to the trans- configuration, thus preventing the lactonization. In the crystal there no formal intramolecular hydrogen bonds (Fig. 2).

This work represents the first structural characterization of this (1R,4R)- aza and oxa bicyclic chiral lactone characterized by X-ray analysis.

Related literature top

For background information on 5-hydroxypipecolic acid and related compounds, see: Witkop & Foltz (1957); Hoarau et al. (1996); Sun et al. (2008). For the synthesis of a related compound, see: Krishnamurthy et al. (2014). For crystal structures of related lactones, including the (1S,4S) conformer, see: Moriguchi, Krishnamurthy, Arai & Tsuge (2014); Moriguchi, Krishnamurthy, Arai, Matsumoto et al. (2014).

Experimental top

The basic reaction scheme for preparation of the title compound (I) is shown in Fig. 3. To a ice cooled solution of 4 mol/L HCl in 1,4-dioxane (16 mL), a solution of diastereomeric (1) ( 0.97 g, 3.56 mmol) in 0.5 mL of 1,4-dioxane was added. This reaction mixture was then warmed to room temperature and stirred. After 3 h most of the volatile materials were removed under vacuum resulting in a crude oily mixture. Trituration with diethyl ether followed by decantation resulted in (2) as a foam (0.71 g, 95 %). DIEA (0.89 mL, 5.07 mmol) was added to a solution of (2) ( 0.71 g, 3.38 mmol) in DMF (13 mL) and stirred at 50 °C. After 6 h the solution was warmed to room temperature, followed by addition of Boc₂O (3.96 g, 18.1 mmol), additional DIEA (0.3 mL, 1.69 mmol) and stirred at room temperature for 18 h. The DMF was evaporated and the crude mixture was subsequently washed with 10% aqueous citric acid, 4% aqueous NaHCO₃, brine, dried (MgSO₄), filtered and evaporated to obtain an oil. The crude product was purified by silica gel column chromatography with (CHCl₃/MeOH, 100:0 to 98:2, v/v) to yield (1R,4R), (I) (0.18 g, 23%) as a white solid. Single crystals were obtained by vapour diffusion method at room temperature, i.e., hexane vapour was allowed to diffuse into an EtOAc (0.5 ml) solution of (1R,4R), (I) at room temperature. Single crystals suitable for analysis were obtained after a week.

¹H NMR 4.61-4.82 (2H, m), 3.63 (1H, m), 3.45 (1H, m), 2.22 (1H, br s), 2.11 (1H, m), 2.00 (1H, m), 1.80 (1H, m), 1.47 (9H, s); MS (FAB m/z): 228 (74), 190 (44), 172 (100), 137 (50), 128 (68), 55 (47). HRMS(FAB) calcd for C₁₁H₁₈N₁O₄ [M + H]⁺ 228.12358, found 228.1243

Computing details top

Data collection: APEX2 (Bruker,2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular configuration and atom numbering scheme for the title compound with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.
	Fig. 2. Crystal packing diagram of the title compound.
	Fig. 3. Synthetic scheme for the title compound (I).

(1R,4R)-tert-butyl 3-oxo-2-oxa-5-azabicyclo[2.2.2]octane-5-carboxylate top

Crystal data top

C₁₁H₁₇NO₄	D_x = 1.318 Mg m⁻³
M_r = 227.26	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 9630 reflections
a = 9.6472 (4) Å	θ = 2.7–28.7°
b = 9.7084 (4) Å	µ = 0.10 mm⁻¹
c = 12.2323 (5) Å	T = 90 K
V = 1145.66 (8) Å³	Prism, colorless
Z = 4	0.45 × 0.40 × 0.40 mm
F(000) = 488

Data collection top

Bruker APEX2 KY CCD diffractometer	2791 independent reflections
Radiation source: fine-focus sealed tube	2728 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 16.6666 pixels mm^-1	θ_max = 28.7°, θ_min = 2.7°
ϕ and ω–scans	h = −12→12
Absorption correction: multi-scan SADABS (Bruker, 2009)	k = −12→12
T_min = 0.870, T_max = 0.961	l = −16→16
13518 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.030	w = 1/[σ²(F_o²) + (0.0583P)² + 0.1302P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.081	(Δ/σ)_max < 0.001
S = 1.02	Δρ_max = 0.24 e Å⁻³
2791 reflections	Δρ_min = −0.27 e Å⁻³
148 parameters	Extinction correction: SHELXL97
0 restraints	Extinction coefficient: 0.0015
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2933 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.1 (7)

Crystal data top

C₁₁H₁₇NO₄	V = 1145.66 (8) Å³
M_r = 227.26	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.6472 (4) Å	µ = 0.10 mm⁻¹
b = 9.7084 (4) Å	T = 90 K
c = 12.2323 (5) Å	0.45 × 0.40 × 0.40 mm

Data collection top

Bruker APEX2 KY CCD diffractometer	2791 independent reflections
Absorption correction: multi-scan SADABS (Bruker, 2009)	2728 reflections with I > 2σ(I)
T_min = 0.870, T_max = 0.961	R_int = 0.021
13518 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.081	Δρ_max = 0.24 e Å⁻³
S = 1.02	Δρ_min = −0.27 e Å⁻³
2791 reflections	Absolute structure: Flack (1983), 2933 Friedel pairs
148 parameters	Absolute structure parameter: 0.1 (7)
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
C1	0.65404 (10)	0.31574 (9)	0.06026 (7)	0.01427 (18)
H1	0.71	0.2937	−0.0063	0.017*
C2	0.49996 (10)	0.33409 (10)	0.03171 (8)	0.0176 (2)
H2A	0.4628	0.2485	−0.0011	0.021*
H2B	0.4883	0.41	−0.0215	0.021*
C3	0.42204 (10)	0.36786 (11)	0.13907 (9)	0.0206 (2)
H3B	0.378	0.4597	0.1335	0.025*
H3A	0.3485	0.2987	0.1521	0.025*
C4	0.52501 (11)	0.36654 (10)	0.23335 (8)	0.01785 (19)
H4	0.475	0.3836	0.3037	0.021*
C5	0.63878 (10)	0.47291 (11)	0.21909 (8)	0.0178 (2)
H5B	0.5993	0.567	0.2175	0.021*
H5A	0.7064	0.4671	0.2798	0.021*
C6	0.66134 (10)	0.19956 (10)	0.14366 (8)	0.01762 (19)
C7	0.81399 (10)	0.51222 (9)	0.07261 (8)	0.01444 (19)
C8	0.96933 (10)	0.70326 (10)	0.12123 (8)	0.01618 (19)
C9	1.10001 (11)	0.61760 (12)	0.11084 (11)	0.0276 (2)
H9A	1.0964	0.5638	0.0431	0.041*
H9B	1.1072	0.5551	0.1735	0.041*
H9C	1.181	0.6785	0.1092	0.041*
C10	0.94288 (14)	0.79172 (11)	0.02135 (10)	0.0272 (3)
H10A	0.8622	0.8507	0.0345	0.041*
H10B	0.925	0.7324	−0.0419	0.041*
H10C	1.0243	0.8492	0.0069	0.041*
C11	0.97332 (14)	0.79157 (13)	0.22359 (10)	0.0311 (3)
H11A	0.9866	0.7325	0.2877	0.047*
H11B	0.8858	0.842	0.2307	0.047*
H11C	1.0502	0.8572	0.2184	0.047*
N1	0.70560 (9)	0.44009 (8)	0.11448 (7)	0.01612 (17)
O1	0.71703 (8)	0.08995 (8)	0.13238 (7)	0.02526 (18)
O2	0.59161 (8)	0.23044 (8)	0.23684 (6)	0.01975 (16)
O3	0.86922 (8)	0.48744 (7)	−0.01469 (6)	0.01893 (16)
O4	0.84801 (7)	0.61426 (7)	0.14236 (6)	0.01846 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0141 (4)	0.0119 (4)	0.0168 (4)	−0.0019 (3)	0.0008 (3)	−0.0028 (3)
C2	0.0155 (5)	0.0172 (4)	0.0201 (4)	−0.0010 (4)	−0.0030 (3)	−0.0007 (3)
C3	0.0129 (4)	0.0230 (5)	0.0259 (5)	0.0005 (4)	0.0000 (4)	−0.0014 (4)
C4	0.0160 (4)	0.0179 (4)	0.0196 (4)	−0.0001 (4)	0.0032 (4)	−0.0012 (4)
C5	0.0166 (4)	0.0198 (4)	0.0172 (4)	−0.0019 (4)	0.0050 (3)	−0.0052 (3)
C6	0.0143 (4)	0.0171 (4)	0.0215 (5)	−0.0016 (3)	−0.0017 (4)	−0.0002 (4)
C7	0.0145 (4)	0.0126 (4)	0.0162 (4)	0.0002 (3)	−0.0017 (3)	0.0000 (3)
C8	0.0151 (4)	0.0155 (4)	0.0179 (4)	−0.0058 (4)	−0.0001 (3)	−0.0001 (3)
C9	0.0166 (5)	0.0241 (5)	0.0421 (6)	−0.0010 (4)	−0.0024 (4)	0.0012 (5)
C10	0.0361 (6)	0.0179 (5)	0.0275 (5)	−0.0039 (4)	−0.0051 (4)	0.0051 (4)
C11	0.0330 (6)	0.0349 (6)	0.0255 (6)	−0.0171 (5)	0.0039 (5)	−0.0126 (5)
N1	0.0161 (4)	0.0161 (4)	0.0162 (4)	−0.0040 (3)	0.0032 (3)	−0.0056 (3)
O1	0.0252 (4)	0.0171 (3)	0.0334 (4)	0.0050 (3)	−0.0025 (4)	0.0002 (3)
O2	0.0211 (4)	0.0186 (3)	0.0195 (3)	0.0009 (3)	0.0015 (3)	0.0029 (3)
O3	0.0219 (4)	0.0184 (3)	0.0165 (3)	−0.0038 (3)	0.0041 (3)	−0.0022 (3)
O4	0.0175 (3)	0.0185 (3)	0.0194 (3)	−0.0073 (3)	0.0040 (3)	−0.0059 (3)

Geometric parameters (Å, º) top

C1—N1	1.4645 (11)	C6—O2	1.3570 (12)
C1—C6	1.5225 (13)	C7—O3	1.2175 (12)
C1—C2	1.5373 (14)	C7—O4	1.3481 (11)
C1—H1	1.0	C7—N1	1.3587 (12)
C2—C3	1.5482 (14)	C8—O4	1.4776 (11)
C2—H2A	0.99	C8—C9	1.5156 (15)
C2—H2B	0.99	C8—C10	1.5150 (14)
C3—C4	1.5222 (15)	C8—C11	1.5180 (14)
C3—H3B	0.99	C9—H9A	0.98
C3—H3A	0.99	C9—H9B	0.98
C4—O2	1.4699 (13)	C9—H9C	0.98
C4—C5	1.5171 (13)	C10—H10A	0.98
C4—H4	1.0	C10—H10B	0.98
C5—N1	1.4677 (12)	C10—H10C	0.98
C5—H5B	0.99	C11—H11A	0.98
C5—H5A	0.99	C11—H11B	0.98
C6—O1	1.2000 (12)	C11—H11C	0.98

N1—C1—C6	106.95 (7)	O3—C7—O4	126.43 (9)
N1—C1—C2	109.62 (8)	O3—C7—N1	124.45 (9)
C6—C1—C2	106.43 (8)	O4—C7—N1	109.12 (8)
N1—C1—H1	111.2	O4—C8—C9	110.65 (8)
C6—C1—H1	111.2	O4—C8—C10	109.82 (8)
C2—C1—H1	111.2	C9—C8—C10	112.55 (9)
C1—C2—C3	107.54 (8)	O4—C8—C11	101.89 (8)
C1—C2—H2A	110.2	C9—C8—C11	110.98 (10)
C3—C2—H2A	110.2	C10—C8—C11	110.44 (9)
C1—C2—H2B	110.2	C8—C9—H9A	109.5
C3—C2—H2B	110.2	C8—C9—H9B	109.5
H2A—C2—H2B	108.5	H9A—C9—H9B	109.5
C4—C3—C2	108.91 (8)	C8—C9—H9C	109.5
C4—C3—H3B	109.9	H9A—C9—H9C	109.5
C2—C3—H3B	109.9	H9B—C9—H9C	109.5
C4—C3—H3A	109.9	C8—C10—H10A	109.5
C2—C3—H3A	109.9	C8—C10—H10B	109.5
H3B—C3—H3A	108.3	H10A—C10—H10B	109.5
O2—C4—C5	107.40 (8)	C8—C10—H10C	109.5
O2—C4—C3	108.35 (8)	H10A—C10—H10C	109.5
C5—C4—C3	112.29 (9)	H10B—C10—H10C	109.5
O2—C4—H4	109.6	C8—C11—H11A	109.5
C5—C4—H4	109.6	C8—C11—H11B	109.5
C3—C4—H4	109.6	H11A—C11—H11B	109.5
N1—C5—C4	105.68 (8)	C8—C11—H11C	109.5
N1—C5—H5B	110.6	H11A—C11—H11C	109.5
C4—C5—H5B	110.6	H11B—C11—H11C	109.5
N1—C5—H5A	110.6	C7—N1—C1	121.03 (8)
C4—C5—H5A	110.6	C7—N1—C5	123.69 (8)
H5B—C5—H5A	108.7	C1—N1—C5	115.13 (8)
O1—C6—O2	120.96 (9)	C6—O2—C4	113.01 (7)
O1—C6—C1	126.91 (9)	C7—O4—C8	120.79 (7)
O2—C6—C1	112.10 (8)

N1—C1—C2—C3	−56.55 (10)	C6—C1—N1—C7	123.18 (10)
C6—C1—C2—C3	58.77 (10)	C2—C1—N1—C7	−121.84 (9)
C1—C2—C3—C4	−1.58 (11)	C6—C1—N1—C5	−52.53 (11)
C2—C3—C4—O2	−57.69 (10)	C2—C1—N1—C5	62.46 (10)
C2—C3—C4—C5	60.76 (11)	C4—C5—N1—C7	−179.64 (9)
O2—C4—C5—N1	61.20 (10)	C4—C5—N1—C1	−4.06 (11)
C3—C4—C5—N1	−57.81 (10)	O1—C6—O2—C4	−177.27 (9)
N1—C1—C6—O1	−126.60 (11)	C1—C6—O2—C4	0.91 (11)
C2—C1—C6—O1	116.29 (11)	C5—C4—O2—C6	−61.30 (10)
N1—C1—C6—O2	55.36 (10)	C3—C4—O2—C6	60.21 (10)
C2—C1—C6—O2	−61.75 (10)	O3—C7—O4—C8	−4.98 (15)
O3—C7—N1—C1	5.74 (15)	N1—C7—O4—C8	175.60 (8)
O4—C7—N1—C1	−174.83 (8)	C10—C8—O4—C7	67.57 (11)
O3—C7—N1—C5	−178.93 (9)	C9—C8—O4—C7	−57.30 (12)
O4—C7—N1—C5	0.50 (13)	C11—C8—O4—C7	−175.35 (9)

Experimental details

Crystal data
Chemical formula	C₁₁H₁₇NO₄
M_r	227.26
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	90
a, b, c (Å)	9.6472 (4), 9.7084 (4), 12.2323 (5)
V (Å³)	1145.66 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.45 × 0.40 × 0.40

Data collection
Diffractometer	Bruker APEX2 KY CCD diffractometer
Absorption correction	Multi-scan SADABS (Bruker, 2009)
T_min, T_max	0.870, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	13518, 2791, 2728
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.081, 1.02
No. of reflections	2791
No. of parameters	148
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.27
Absolute structure	Flack (1983), 2933 Friedel pairs
Absolute structure parameter	0.1 (7)

Computer programs: APEX2 (Bruker,2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

We are grateful to the Center for Instrumental Analysis, Kyushu Institute of Technology (KITCIA), for high-resolution mass and ¹H NMR spectra and X-ray analysis.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Hoarau, S., Fauchère, J. L., Pappalardo, L., Roumestant, M. L. & Viallefont, P. (1996). Tetrahedron Asymmetry, 7, 2585–2593. CrossRef CAS Web of Science Google Scholar
Krishnamurthy, S., Arai, T., Nakanishi, K. & Nishino, N. (2014). RSC Adv. 4, 2482–2490. Web of Science CrossRef CAS Google Scholar
Moriguchi, T., Krishnamurthy, S., Arai, T., Matsumoto, T., Araki, K., Tsuge, A. & Nishino, N. (2014). J. Crystallogr.: doi 10.1155/2014/645079 Google Scholar
Moriguchi, T., Krishnamurthy, S., Arai, T. & Tsuge, A. (2014). J. Crystallogr.: doi 10.1155/2014/150796. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, C. S., Lin, Y. S. & Hou, D. R. (2008). J. Org. Chem. 73, 6877–6880. Web of Science CrossRef PubMed CAS Google Scholar
Witkop, B. & Foltz, C. M. (1957). J. Am. Chem. Soc. 79, 192–197. CrossRef CAS Web of Science Google Scholar

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