1,2-Diphenyl­ethane-1,2-diyl diiso­nico­tinate monohydrate

Yan, J.; Qi, M.; Haitao, X.; Xiaoqiang, S.; Xin, W.

doi:10.1107/S1600536808022484

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1992

doi:10.1107/S1600536808022484

Open

access

1,2-Diphenylethane-1,2-diyl diisonicotinate monohydrate †

Jiang Yan,^a ‡ Meng Qi,^b Xi Haitao,^b Sun Xiaoqiang ^b ^* and Wang Xin ^a

^aMaterials Chemistry Laboratory, Nanjing University of Science and Technology, Nanjing 210094, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, Jiangsu Polytechnic University, Changzhou 213164, People's Republic of China
^*Correspondence e-mail: xieyima@hotmail.com

(Received 14 June 2008; accepted 17 July 2008; online 24 September 2008)

In the novel title compound, C₂₆H₂₀N₂O₄·H₂O, the two phenyl rings make a dihedral angle of 45.3 (1)° with each other, and the dihedral angle between the two pyridyl planes is 69.8 (1)°.

Related literature

For general background, see: Aspinall et al. (2003 ); Takenaka et al. (2006 ); MacMahon et al. (2001 ); Schuster et al. (2005 ). For related structures, see: Shi et al. (2006 ).

Experimental

Crystal data

C₂₆H₂₀N₂O₄·H₂O
M_r = 442.46
Monoclinic, P 2₁
a = 11.925 (10) Å
b = 5.826 (5) Å
c = 17.787 (15) Å
β = 105.629 (10)°
V = 1190.1 (17) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 291 (2) K
0.32 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker,2000 ) T_min = 0.979, T_max = 0.981
6535 measured reflections
2566 independent reflections
1816 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.086
S = 1.10
2566 reflections
304 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5B⋯N2ⁱ	0.84 (4)	2.48 (5)	2.921 (4)	113 (4)
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks z0612, I. DOI: 10.1107/S1600536808022484/sg2251sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022484/sg2251Isup2.hkl

checkCIF report

Comment top

Synthesis of chiral molecules containing pyridine rings has attracted considerable attention in recent years (Aspinall, et al., 2003; Takenaka, et al., 2006; MacMahon, et al., 2001; Schuster, et al., 2005). In the title compound, (I), C₂₆H₂₀NO₂, all bond lengths and angles show normal values (Shi, et al., 2006). The chiral molecule (Figure 1) consists of two benzene rings and two pyridine rings. The dihedral angle between the two benzene ring is 45.28°. The torsion angle C2—C1—C7—O2 is -44.2 (2)°; the torsional angle The packing arrangement in a unit cell of the title molecule is shown in Figure 2.

Related literature top

For related literature, see: Aspinall et al. (2003); Takenaka et al. (2006); MacMahon et al. (2001); Schuster et al. (2005); Shi et al. (2006).It would be much more useful to readers if the "Related literature" section had some kind of simple sub-division, so that, instead of just "For related literature, see···" it said, for example, "For general background, see···. For related structures, see···.? etc. Please revise this section as indicated.

Experimental top

The title compound, was synthesized by the reaction of trans-1,2-stilbene with nicotinic acid in dichloromethane. The single crystals of (I) suitable for X-ray diffraction were obtained from an ethanol solution by slow evaporation.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing 20% probability displacement ellipsoids.
	Fig. 2. The molecular packing diagram in the crystal for (I).

(1R,2R)-1,2-Diphenylethane-1,2-diyl diisonicotinate monohydrate top

Crystal data top

C₂₆H₂₀N₂O₄·H₂O	F(000) = 464
M_r = 442.46	D_x = 1.235 Mg m⁻³
Monoclinic, P2₁	Melting point: 327 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 11.925 (10) Å	Cell parameters from 1142 reflections
b = 5.826 (5) Å	θ = 2.4–21.6°
c = 17.787 (15) Å	µ = 0.09 mm⁻¹
β = 105.629 (10)°	T = 291 K
V = 1190.1 (17) Å³	Acicular, colorless
Z = 2	0.32 × 0.24 × 0.22 mm

Data collection top

Bruker SMART APEX CCD diffractometer	2566 independent reflections
Radiation source: sealed tube	1816 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
phi and ω scans	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker,2000)	h = −14→14
T_min = 0.979, T_max = 0.981	k = −7→7
6535 measured reflections	l = −21→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.030P)²] where P = (F_o² + 2F_c²)/3
2566 reflections	(Δ/σ)_max < 0.001
304 parameters	Δρ_max = 0.13 e Å⁻³
1 restraint	Δρ_min = −0.11 e Å⁻³

Crystal data top

C₂₆H₂₀N₂O₄·H₂O	V = 1190.1 (17) Å³
M_r = 442.46	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 11.925 (10) Å	µ = 0.09 mm⁻¹
b = 5.826 (5) Å	T = 291 K
c = 17.787 (15) Å	0.32 × 0.24 × 0.22 mm
β = 105.629 (10)°

Data collection top

Bruker SMART APEX CCD diffractometer	2566 independent reflections
Absorption correction: multi-scan (SADABS; Bruker,2000)	1816 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.981	R_int = 0.024
6535 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	1 restraint
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.13 e Å⁻³
2566 reflections	Δρ_min = −0.11 e Å⁻³
304 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
C1	0.1366 (3)	0.0950 (8)	0.1997 (2)	0.0617 (9)
H1	0.1843	0.0198	0.2426	0.074*
C2	0.0250 (3)	0.0040 (7)	0.1606 (2)	0.0610 (10)
H2	0.0002	−0.1319	0.1784	0.073*
C3	−0.0446 (3)	0.1107 (7)	0.0988 (2)	0.0658 (10)
H3	−0.1171	0.0486	0.0744	0.079*
C4	−0.0107 (3)	0.3060 (7)	0.0718 (2)	0.0644 (10)
H4	−0.0598	0.3783	0.0287	0.077*
C5	0.1006 (3)	0.4042 (7)	0.1088 (2)	0.0604 (9)
H5	0.1237	0.5395	0.0895	0.072*
C6	0.1729 (3)	0.2994 (6)	0.17230 (19)	0.0526 (8)
C7	0.2931 (2)	0.3938 (6)	0.20841 (16)	0.0479 (8)
H7	0.2980	0.5524	0.1912	0.058*
C8	0.3874 (3)	0.2465 (7)	0.18741 (17)	0.0520 (8)
H8	0.3854	0.0892	0.2065	0.062*
C9	0.3699 (2)	0.2474 (6)	0.10007 (17)	0.0454 (7)
C10	0.3172 (3)	0.0645 (7)	0.05519 (19)	0.0575 (9)
H10	0.2938	−0.0621	0.0790	0.069*
C11	0.2988 (3)	0.0677 (7)	−0.0256 (2)	0.0592 (9)
H11	0.2647	−0.0576	−0.0555	0.071*
C12	0.3315 (3)	0.2587 (7)	−0.06095 (19)	0.0545 (8)
H12	0.3165	0.2639	−0.1150	0.065*
C13	0.3855 (3)	0.4387 (7)	−0.01715 (19)	0.0560 (9)
H13	0.4093	0.5640	−0.0414	0.067*
C14	0.4059 (2)	0.4372 (6)	0.06493 (19)	0.0511 (8)
H14	0.4427	0.5604	0.0949	0.061*
C15	0.3427 (3)	0.5843 (7)	0.3341 (2)	0.0534 (8)
C16	0.3422 (3)	0.5479 (7)	0.4175 (2)	0.0586 (9)
C17	0.2955 (3)	0.3621 (7)	0.4423 (2)	0.0629 (10)
H17	0.2644	0.2469	0.4066	0.076*
C18	0.2919 (3)	0.3359 (7)	0.5200 (2)	0.0611 (10)
H18	0.2595	0.2051	0.5356	0.073*
C19	0.3806 (3)	0.6880 (6)	0.5480 (2)	0.0611 (10)
H19	0.4073	0.8048	0.5840	0.073*
C20	0.3910 (3)	0.7229 (7)	0.4693 (2)	0.0639 (10)
H20	0.4270	0.8507	0.4548	0.077*
C21	0.5955 (3)	0.2419 (6)	0.22411 (18)	0.0478 (8)
C22	0.7001 (3)	0.3845 (6)	0.25533 (17)	0.0504 (8)
C23	0.7001 (3)	0.5913 (7)	0.29022 (18)	0.0551 (9)
H23	0.6312	0.6513	0.2971	0.066*
C24	0.8028 (3)	0.7121 (7)	0.3155 (2)	0.0608 (10)
H24	0.8009	0.8528	0.3398	0.073*
C25	0.9004 (3)	0.4385 (8)	0.2745 (2)	0.0661 (10)
H25	0.9706	0.3818	0.2690	0.079*
C26	0.8048 (3)	0.2999 (7)	0.2472 (2)	0.0590 (9)
H26	0.8101	0.1579	0.2245	0.071*
N1	0.3370 (3)	0.5066 (6)	0.57225 (18)	0.0654 (8)
N2	0.9046 (3)	0.6389 (6)	0.30715 (18)	0.0660 (9)
O1	0.31042 (17)	0.3875 (4)	0.29344 (11)	0.0516 (6)
O2	0.36767 (19)	0.7536 (5)	0.30737 (14)	0.0629 (7)
O3	0.49642 (18)	0.3587 (4)	0.22757 (12)	0.0531 (6)
O4	0.59297 (19)	0.0481 (5)	0.19752 (13)	0.0587 (6)
O5	0.0848 (2)	0.9233 (6)	0.40864 (18)	0.0779 (9)
H5A	0.059 (4)	0.815 (9)	0.424 (3)	0.093*
H5B	0.047 (3)	0.947 (8)	0.362 (3)	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.061 (2)	0.065 (3)	0.058 (2)	0.0020 (18)	0.0136 (18)	0.0043 (19)
C2	0.063 (2)	0.059 (3)	0.061 (2)	−0.0087 (17)	0.0178 (19)	−0.0038 (18)
C3	0.062 (2)	0.069 (3)	0.064 (2)	−0.010 (2)	0.0140 (19)	−0.015 (2)
C4	0.060 (2)	0.067 (3)	0.062 (2)	0.0080 (19)	0.0089 (18)	−0.005 (2)
C5	0.0522 (18)	0.063 (2)	0.064 (2)	0.0058 (18)	0.0123 (16)	−0.001 (2)
C6	0.0556 (19)	0.057 (2)	0.0475 (18)	−0.0030 (16)	0.0178 (15)	−0.0043 (17)
C7	0.0533 (17)	0.057 (2)	0.0308 (15)	0.0098 (16)	0.0067 (13)	0.0048 (15)
C8	0.0542 (18)	0.062 (2)	0.0420 (17)	−0.0031 (16)	0.0175 (15)	0.0039 (16)
C9	0.0432 (15)	0.053 (2)	0.0411 (18)	0.0037 (15)	0.0136 (14)	−0.0001 (16)
C10	0.0568 (19)	0.065 (2)	0.050 (2)	−0.0001 (18)	0.0130 (16)	−0.0030 (19)
C11	0.061 (2)	0.061 (2)	0.054 (2)	−0.0055 (19)	0.0127 (17)	−0.0121 (19)
C12	0.0562 (18)	0.067 (2)	0.0429 (19)	0.0085 (18)	0.0180 (16)	0.0023 (18)
C13	0.0502 (17)	0.064 (2)	0.0525 (19)	0.0065 (17)	0.0121 (15)	0.0081 (18)
C14	0.0488 (17)	0.059 (2)	0.0481 (18)	−0.0065 (17)	0.0179 (14)	−0.0004 (17)
C15	0.0568 (19)	0.052 (2)	0.053 (2)	0.0120 (17)	0.0188 (16)	0.0071 (19)
C16	0.064 (2)	0.062 (2)	0.0490 (18)	−0.0077 (18)	0.0140 (16)	−0.0006 (18)
C17	0.066 (2)	0.066 (3)	0.055 (2)	−0.0181 (18)	0.0140 (18)	−0.0070 (19)
C18	0.067 (2)	0.059 (2)	0.055 (2)	−0.0162 (18)	0.0121 (17)	0.0051 (18)
C19	0.065 (2)	0.060 (2)	0.057 (2)	−0.0133 (19)	0.0159 (17)	−0.0154 (19)
C20	0.0620 (19)	0.063 (2)	0.065 (2)	−0.0051 (18)	0.0138 (18)	−0.0064 (19)
C21	0.0522 (17)	0.058 (2)	0.0351 (16)	0.0071 (16)	0.0142 (14)	0.0124 (16)
C22	0.0616 (19)	0.060 (2)	0.0320 (15)	0.0033 (17)	0.0170 (14)	0.0072 (16)
C23	0.060 (2)	0.065 (3)	0.0394 (17)	0.0064 (17)	0.0124 (15)	0.0017 (17)
C24	0.060 (2)	0.063 (3)	0.058 (2)	0.0028 (18)	0.0136 (18)	−0.0088 (18)
C25	0.063 (2)	0.064 (3)	0.072 (2)	−0.001 (2)	0.0174 (19)	−0.011 (2)
C26	0.0579 (19)	0.061 (2)	0.058 (2)	−0.0075 (17)	0.0152 (17)	−0.0077 (18)
N1	0.0718 (19)	0.066 (2)	0.0574 (17)	−0.0158 (16)	0.0152 (15)	−0.0097 (16)
N2	0.0662 (18)	0.066 (2)	0.065 (2)	0.0032 (15)	0.0164 (15)	−0.0170 (17)
O1	0.0563 (13)	0.0607 (16)	0.0372 (12)	−0.0064 (12)	0.0117 (10)	0.0014 (11)
O2	0.0610 (14)	0.0649 (17)	0.0592 (15)	−0.0069 (13)	0.0100 (12)	0.0042 (14)
O3	0.0570 (12)	0.0594 (15)	0.0429 (11)	0.0088 (11)	0.0134 (10)	−0.0027 (11)
O4	0.0579 (13)	0.0690 (17)	0.0498 (13)	0.0184 (13)	0.0153 (10)	−0.0072 (13)
O5	0.0623 (17)	0.073 (2)	0.079 (2)	−0.0134 (15)	−0.0127 (14)	0.0160 (17)

Geometric parameters (Å, º) top

C1—C6	1.399 (5)	C15—O2	1.168 (4)
C1—C2	1.427 (5)	C15—O1	1.354 (4)
C1—H1	0.9300	C15—C16	1.502 (5)
C2—C3	1.339 (5)	C16—C17	1.344 (5)
C2—H2	0.9300	C16—C20	1.392 (5)
C3—C4	1.339 (6)	C17—C18	1.402 (5)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.433 (5)	C18—N1	1.369 (5)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.367 (5)	C19—N1	1.302 (5)
C5—H5	0.9300	C19—C20	1.452 (5)
C6—C7	1.507 (4)	C19—H19	0.9300
C7—O1	1.471 (3)	C20—H20	0.9300
C7—C8	1.538 (4)	C21—O4	1.221 (5)
C7—H7	0.9800	C21—O3	1.379 (4)
C8—O3	1.459 (4)	C21—C22	1.477 (5)
C8—C9	1.511 (4)	C22—C23	1.355 (5)
C8—H8	0.9800	C22—C26	1.386 (4)
C9—C10	1.377 (5)	C23—C24	1.379 (5)
C9—C14	1.394 (5)	C23—H23	0.9300
C10—C11	1.394 (5)	C24—N2	1.333 (4)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.385 (5)	C25—N2	1.298 (5)
C11—H11	0.9300	C25—C26	1.374 (5)
C12—C13	1.361 (5)	C25—H25	0.9300
C12—H12	0.9300	C26—H26	0.9300
C13—C14	1.414 (5)	O5—H5A	0.78 (5)
C13—H13	0.9300	O5—H5B	0.84 (4)
C14—H14	0.9300

C6—C1—C2	118.9 (3)	C9—C14—C13	118.7 (3)
C6—C1—H1	120.6	C9—C14—H14	120.7
C2—C1—H1	120.6	C13—C14—H14	120.7
C3—C2—C1	121.2 (4)	O2—C15—O1	124.4 (3)
C3—C2—H2	119.4	O2—C15—C16	126.2 (4)
C1—C2—H2	119.4	O1—C15—C16	109.4 (3)
C4—C3—C2	120.6 (4)	C17—C16—C20	120.7 (3)
C4—C3—H3	119.7	C17—C16—C15	123.3 (3)
C2—C3—H3	119.7	C20—C16—C15	116.0 (4)
C3—C4—C5	120.4 (4)	C16—C17—C18	122.4 (3)
C3—C4—H4	119.8	C16—C17—H17	118.8
C5—C4—H4	119.8	C18—C17—H17	118.8
C6—C5—C4	120.1 (4)	N1—C18—C17	118.6 (3)
C6—C5—H5	119.9	N1—C18—H18	120.7
C4—C5—H5	119.9	C17—C18—H18	120.7
C5—C6—C1	118.8 (3)	N1—C19—C20	125.3 (3)
C5—C6—C7	120.3 (3)	N1—C19—H19	117.3
C1—C6—C7	120.7 (3)	C20—C19—H19	117.3
O1—C7—C6	106.5 (2)	C16—C20—C19	113.9 (4)
O1—C7—C8	109.0 (2)	C16—C20—H20	123.0
C6—C7—C8	111.5 (3)	C19—C20—H20	123.0
O1—C7—H7	109.9	O4—C21—O3	122.8 (3)
C6—C7—H7	109.9	O4—C21—C22	126.6 (3)
C8—C7—H7	109.9	O3—C21—C22	110.6 (3)
O3—C8—C9	111.1 (2)	C23—C22—C26	118.4 (3)
O3—C8—C7	104.2 (3)	C23—C22—C21	124.6 (3)
C9—C8—C7	109.9 (3)	C26—C22—C21	117.0 (3)
O3—C8—H8	110.5	C22—C23—C24	119.6 (3)
C9—C8—H8	110.5	C22—C23—H23	120.2
C7—C8—H8	110.5	C24—C23—H23	120.2
C10—C9—C14	120.1 (3)	N2—C24—C23	123.8 (4)
C10—C9—C8	120.6 (3)	N2—C24—H24	118.1
C14—C9—C8	119.3 (3)	C23—C24—H24	118.1
C9—C10—C11	120.5 (4)	N2—C25—C26	128.0 (4)
C9—C10—H10	119.7	N2—C25—H25	116.0
C11—C10—H10	119.7	C26—C25—H25	116.0
C12—C11—C10	119.6 (3)	C25—C26—C22	116.0 (3)
C12—C11—H11	120.2	C25—C26—H26	122.0
C10—C11—H11	120.2	C22—C26—H26	122.0
C13—C12—C11	120.5 (3)	C19—N1—C18	118.9 (3)
C13—C12—H12	119.8	C25—N2—C24	114.2 (4)
C11—C12—H12	119.8	C15—O1—C7	117.9 (3)
C12—C13—C14	120.6 (3)	C21—O3—C8	114.7 (3)
C12—C13—H13	119.7	H5A—O5—H5B	108 (4)
C14—C13—H13	119.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···N2ⁱ	0.84 (4)	2.48 (5)	2.921 (4)	113 (4)

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₀N₂O₄·H₂O
M_r	442.46
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	291
a, b, c (Å)	11.925 (10), 5.826 (5), 17.787 (15)
β (°)	105.629 (10)
V (Å³)	1190.1 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.24 × 0.22

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker,2000)
T_min, T_max	0.979, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	6535, 2566, 1816
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.086, 1.10
No. of reflections	2566
No. of parameters	304
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.11

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···N2ⁱ	0.84 (4)	2.48 (5)	2.921 (4)	113 (4)

Symmetry code: (i) x−1, y, z.

Footnotes

†Contribution No 20272019.

‡Current address: Department of Chemistry and Chemical Engineering, Jiangsu Polytechnic University, People's Republic of China.

Acknowledgements

We thank the Natural Science Foundation of China (No. 20272019) and the Key Laboratory of Fine Petrochemical Engineering of Jiangsu Province (KF0503) for financial support.

References

Aspinall, H. C., Greeves, N. & McIver, E. G. (2003). Tetrahedron, 59, 10453–10463. Web of Science CSD CrossRef CAS Google Scholar
Bruker, (2000). SMART, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
MacMahon, S. R., Fong, P. S., Baran, S. I., Wilson, S. R. & Schuster, D. I. (2001). J. Org. Chem. 66, 5449–5455. Web of Science CrossRef PubMed CAS Google Scholar
Schuster, C., Knollmueller, M. & Gaertner, P. (2005). Tetrahedron Asymmetry, 16, 2631–2647. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, S.-M., Jia, B., Wu, Y., Liu, X.-D. & Hu, Z.-Q. (2006). Acta Cryst. E62, o2278–o2280. Web of Science CSD CrossRef IUCr Journals Google Scholar
Takenaka, Y., Ito, H., Hasegawa, M. & Iguchi, K. (2006). Tetrahedron, 62, 3380–3388. Web of Science CrossRef CAS Google Scholar