8-Methyl-5-methyl­ene-2-oxotricyclo[5.3.1.13,9]dodecan-endo-8-ol

Chan, I.Y.H.; Bishop, R.; Craig, D.C.; Scudder, M.L.; Yue, W.

doi:10.1107/S1600536808009677

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o841

doi:10.1107/S1600536808009677

Open

access

8-Methyl-5-methylene-2-oxotricyclo[5.3.1.1^3,9]dodecan-endo-8-ol

Isa Y. H. Chan,^a Roger Bishop,^a Donald C. Craig,^a Marcia L. Scudder ^a ^* and Weimin Yue ^b

^aSchool of Chemistry, University of New South Wales, Sydney 2052, Australia, and ^bSchool of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, People's Republic of China
^*Correspondence e-mail: m.scudder@unsw.edu.au

(Received 7 April 2008; accepted 8 April 2008; online 16 April 2008)

The title compound, C₁₄H₂₀O₂, crystallizes with homochiral chains of molecules hydrogen bonded together along the b axis. Adjacent chains in the ab plane contain molecules of the same chirality, leading to a chiral segregation of the molecules into layers.

Related literature

For related literature, see: Yue et al. (2002 , 2006 , 2007 , 1997 , 2000 ).

Experimental

Crystal data

C₁₄H₂₀O₂
M_r = 220.3
Monoclinic, P 2₁ /c
a = 7.554 (3) Å
b = 13.196 (3) Å
c = 12.597 (5) Å
β = 108.16 (2)°
V = 1193.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 294 K
0.25 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
2247 measured reflections
2079 independent reflections
1296 reflections with I > 2σ(I)
R_int = 0.016
1 standard reflection frequency: 30 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.052
S = 1.27
2079 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2ⁱ	1.00	1.87	2.867 (4)	180
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: local program; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: RAELS (Rae, 2000 ); molecular graphics: ORTEPII (Johnson, 1976 ) and CrystalMaker (Palmer, 2005 ); software used to prepare material for publication: local programs.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808009677/hg2391sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009677/hg2391Isup2.hkl

checkCIF report

Comment top

The preparation of this compound is part of a project involving alicyclic diols (Yue et al. 2002, 2006, 2007). The title compound (Fig. 1) crystallizes in space group P2₁/c with homochiral chains of molecules along b which are held together by O—H···O═C hydrogen bonding. Adjacent chains along a are of the same chirality, leading to chirally pure layers within the crystal which are shaded light and dark in Fig. 2. It is unusual to observe chirally pure layers within a centrosymmetric lattice. In this case the layer is generated by a combination of the 2₁ screw axis along b and translation along the short a axis, neither of which generates a change in chirality.

Related literature top

For related literature, see: Yue et al. (2002, 2006, 2007, 1997, 2000)).

Experimental top

5-Methylidenetricyclo[5.3.1.1^3,9]dodecane-2,8-dione (Yue et al., 1997, 2000) was reacted with ca 1 equivalent of methyllithium in tetrahydrofuran solution. After standard work up of the reaction, the crude solid product was recrystallized to afford the title compound of m.p. 105–107°C. ¹³C NMR (75.5 MHz, CDCl₃) δ: 28.1 (CH₂), 30.9 (CH₂), 31.9 (CH₃), 34.7 (CH₂), 38.6 (CH₂), 38.8 (CH), 40.6 (CH), 42.7 (CH), 43.3 (CH), 45.3 (CH₂), 74.8 (C), 119.3 (CH₂), 148.2 (C), 219.9 (C). ¹H NMR (300 MHz, CDCl₃) δ: 1.44 (s, 3H), 1.83–1.98 (m, 4H), 2.01–2.21 (m, 4H), 2.29–2.47 (m, 4H), 2.66–2.76 (m, 2H), 2.99 (dd, J = 14.3, 7.1 Hz, 1H), 4.94 (d, J = 15.1 Hz, 2H). X-ray quality crystals were obtained from diethyl ether solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: local program; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: RAELS (Rae, 2000); molecular graphics: ORTEPII (Johnson, 1976) and CrystalMaker (Palmer, 2005); software used to prepare material for publication: local programs.

Figures top

	Fig. 1. Molecular structure of the compound, with ellipsoids drawn at 30% probability level.
	Fig. 2. Unit cell diagram showing the O—H···O═C hydrogen bonded chain along b. Adjacent layers along c are chirally pure with alternating chirality. This is indicated by light and dark shading of C atoms.

8-Methyl-5-methylene-2-oxotricyclo[5.3.1.1^3,9]dodecan-endo-8-ol top

Crystal data top

C₁₄H₂₀O₂	F(000) = 480.0
M_r = 220.3	D_x = 1.23 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.554 (3) Å	Cell parameters from 11 reflections
b = 13.196 (3) Å	θ = 10–11°
c = 12.597 (5) Å	µ = 0.08 mm⁻¹
β = 108.16 (2)°	T = 294 K
V = 1193.2 (7) Å³	Block, colourless
Z = 4	0.25 × 0.20 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	θ_max = 25°
ω/2θ scans	h = 0→8
2247 measured reflections	k = 0→15
2079 independent reflections	l = −15→15
1296 reflections with I > 2σ(I)	1 standard reflections every 30 min
R_int = 0.016	intensity decay: none

Refinement top

Refinement on F	0 restraints
R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.052	w = 1/[σ²(F) + 0.0004F²]
S = 1.27	(Δ/σ)_max = 0.003
2079 reflections	Δρ_max = 0.28 e Å⁻³
145 parameters	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₄H₂₀O₂	V = 1193.2 (7) Å³
M_r = 220.3	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.554 (3) Å	µ = 0.08 mm⁻¹
b = 13.196 (3) Å	T = 294 K
c = 12.597 (5) Å	0.25 × 0.20 × 0.20 mm
β = 108.16 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.016
2247 measured reflections	1 standard reflections every 30 min
2079 independent reflections	intensity decay: none
1296 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.052	H-atom parameters constrained
S = 1.27	Δρ_max = 0.28 e Å⁻³
2079 reflections	Δρ_min = −0.28 e Å⁻³
145 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.5397 (2)	0.2837 (1)	0.1016 (1)	0.0557 (5)
O2	0.6667 (2)	−0.0303 (1)	0.4412 (1)	0.0595 (5)
C1	0.4341 (3)	0.2236 (2)	0.2535 (2)	0.0417 (6)
C2	0.4327 (3)	0.2060 (2)	0.1324 (2)	0.0416 (6)
C3	0.5169 (3)	0.1035 (2)	0.1158 (2)	0.0429 (6)
C4	0.4404 (3)	0.0172 (2)	0.1708 (2)	0.0447 (6)
C5	0.4266 (3)	0.0387 (2)	0.2886 (2)	0.0438 (6)
C6	0.6110 (3)	0.0420 (2)	0.3790 (2)	0.0426 (6)
C7	0.7296 (3)	0.1362 (2)	0.3922 (2)	0.0430 (6)
C8	0.6271 (3)	0.2343 (2)	0.3406 (2)	0.0452 (6)
C9	0.3273 (3)	0.1393 (2)	0.2908 (2)	0.0477 (6)
C10	0.7322 (3)	0.1007 (2)	0.1397 (2)	0.0522 (6)
C11	0.8518 (3)	0.0511 (2)	0.2448 (2)	0.0498 (6)
C12	0.8989 (3)	0.1092 (2)	0.3527 (2)	0.0535 (6)
C13	0.9221 (4)	−0.0409 (2)	0.2436 (2)	0.0705 (8)
C14	0.2323 (4)	0.2130 (2)	0.0531 (2)	0.0609 (7)
H1O1	0.4677	0.3486	0.0866	0.056
HC1	0.3655	0.2883	0.2542	0.042
HC3	0.4643	0.0900	0.0338	0.043
H1C4	0.5236	−0.0429	0.1766	0.045
H2C4	0.3124	0.0005	0.1208	0.045
HC5	0.3507	−0.0165	0.3074	0.044
HC7	0.7811	0.1489	0.4744	0.043
H1C8	0.7085	0.2710	0.3041	0.045
H2C8	0.6119	0.2764	0.4033	0.045
H1C9	0.1969	0.1358	0.2387	0.048
H2C9	0.3247	0.1534	0.3682	0.048
H1C10	0.7751	0.1726	0.1414	0.052
H2C10	0.7558	0.0645	0.0757	0.052
H1C12	0.9612	0.1738	0.3428	0.054
H2C12	0.9872	0.0673	0.4122	0.054
H1C13	0.8958	−0.0787	0.1715	0.071
H2C13	1.0014	−0.0724	0.3147	0.071
H1C14	0.1544	0.1594	0.0728	0.061
H2C14	0.1798	0.2812	0.0604	0.061
H3C14	0.2321	0.2029	−0.0256	0.061

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.080 (1)	0.0411 (9)	0.0500 (9)	−0.0072 (8)	0.0264 (9)	0.0068 (7)
O2	0.071 (1)	0.050 (1)	0.051 (1)	0.0052 (9)	0.0098 (9)	0.0139 (8)
C1	0.047 (1)	0.037 (1)	0.041 (1)	0.005 (1)	0.014 (1)	0.000 (1)
C2	0.052 (2)	0.034 (1)	0.038 (1)	−0.003 (1)	0.013 (1)	0.001 (1)
C3	0.054 (1)	0.040 (1)	0.033 (1)	−0.004 (1)	0.010 (1)	−0.006 (1)
C4	0.049 (2)	0.038 (1)	0.041 (1)	−0.005 (1)	0.005 (1)	−0.003 (1)
C5	0.044 (1)	0.042 (1)	0.045 (1)	−0.005 (1)	0.014 (1)	0.007 (1)
C6	0.052 (2)	0.044 (1)	0.034 (1)	0.002 (1)	0.018 (1)	0.002 (1)
C7	0.048 (1)	0.046 (1)	0.031 (1)	−0.002 (1)	0.008 (1)	−0.005 (1)
C8	0.059 (2)	0.038 (1)	0.038 (1)	−0.003 (1)	0.014 (1)	−0.006 (1)
C9	0.048 (1)	0.052 (1)	0.045 (1)	0.001 (1)	0.018 (1)	0.004 (1)
C10	0.062 (2)	0.055 (2)	0.045 (1)	−0.002 (1)	0.024 (1)	−0.007 (1)
C11	0.041 (1)	0.051 (1)	0.059 (2)	−0.003 (1)	0.019 (1)	−0.006 (1)
C12	0.045 (1)	0.059 (2)	0.052 (1)	−0.002 (1)	0.008 (1)	−0.008 (1)
C13	0.059 (2)	0.060 (2)	0.090 (2)	0.005 (1)	0.019 (2)	−0.008 (2)
C14	0.064 (2)	0.058 (2)	0.050 (1)	0.004 (1)	0.002 (1)	0.008 (1)

Geometric parameters (Å, º) top

O1—C2	1.432 (2)	C7—C8	1.544 (3)
O1—H1O1	1.000	C7—C12	1.551 (3)
O2—C6	1.223 (2)	C7—HC7	1.000
C1—C2	1.540 (3)	C8—H1C8	1.000
C1—C8	1.534 (3)	C8—H2C8	1.000
C1—C9	1.531 (3)	C9—H1C9	1.000
C1—HC1	1.000	C9—H2C9	1.000
C2—C3	1.536 (3)	C10—C11	1.501 (3)
C2—C14	1.535 (3)	C10—H1C10	1.000
C3—C4	1.536 (3)	C10—H2C10	1.000
C3—C10	1.560 (3)	C11—C12	1.503 (3)
C3—HC3	1.000	C11—C13	1.327 (3)
C4—C5	1.546 (3)	C12—H1C12	1.000
C4—H1C4	1.000	C12—H2C12	1.000
C4—H2C4	1.000	C13—H1C13	1.000
C5—C6	1.500 (3)	C13—H2C13	1.000
C5—C9	1.529 (3)	C14—H1C14	1.000
C5—HC5	1.000	C14—H2C14	1.000
C6—C7	1.511 (3)	C14—H3C14	1.000

C2—O1—H1O1	110.1	C8—C7—HC7	106.1
C2—C1—C8	115.7 (2)	C12—C7—HC7	106.1
C2—C1—C9	110.7 (2)	C1—C8—C7	117.6 (2)
C2—C1—HC1	107.1	C1—C8—H1C8	107.4
C8—C1—C9	108.7 (2)	C1—C8—H2C8	107.4
C8—C1—HC1	107.1	C7—C8—H1C8	107.4
C9—C1—HC1	107.1	C7—C8—H2C8	107.4
O1—C2—C1	109.3 (2)	H1C8—C8—H2C8	109.5
O1—C2—C3	107.5 (2)	C1—C9—C5	108.5 (2)
O1—C2—C14	107.8 (2)	C1—C9—H1C9	109.7
C1—C2—C3	113.1 (2)	C1—C9—H2C9	109.7
C1—C2—C14	109.6 (2)	C5—C9—H1C9	109.7
C3—C2—C14	109.3 (2)	C5—C9—H2C9	109.7
C2—C3—C4	111.2 (2)	H1C9—C9—H2C9	109.5
C2—C3—C10	116.5 (2)	C3—C10—C11	119.0 (2)
C2—C3—HC3	104.4	C3—C10—H1C10	107.0
C4—C3—C10	114.3 (2)	C3—C10—H2C10	107.0
C4—C3—HC3	104.4	C11—C10—H1C10	107.0
C10—C3—HC3	104.4	C11—C10—H2C10	107.0
C3—C4—C5	116.3 (2)	H1C10—C10—H2C10	109.5
C3—C4—H1C4	107.7	C10—C11—C12	118.8 (2)
C3—C4—H2C4	107.7	C10—C11—C13	121.5 (2)
C5—C4—H1C4	107.7	C12—C11—C13	119.6 (2)
C5—C4—H2C4	107.7	C7—C12—C11	114.9 (2)
H1C4—C4—H2C4	109.5	C7—C12—H1C12	108.1
C4—C5—C6	114.2 (2)	C7—C12—H2C12	108.1
C4—C5—C9	110.9 (2)	C11—C12—H1C12	108.1
C4—C5—HC5	107.9	C11—C12—H2C12	108.1
C6—C5—C9	107.8 (2)	H1C12—C12—H2C12	109.5
C6—C5—HC5	107.9	C11—C13—H1C13	120.0
C9—C5—HC5	107.9	C11—C13—H2C13	120.0
O2—C6—C5	121.1 (2)	H1C13—C13—H2C13	120.0
O2—C6—C7	119.9 (2)	C2—C14—H1C14	109.5
C5—C6—C7	119.1 (2)	C2—C14—H2C14	109.5
C6—C7—C8	116.2 (2)	C2—C14—H3C14	109.5
C6—C7—C12	107.2 (2)	H1C14—C14—H2C14	109.5
C6—C7—HC7	106.1	H1C14—C14—H3C14	109.5
C8—C7—C12	114.4 (2)	H2C14—C14—H3C14	109.5

H1O1—O1—C2—C1	−75.5	HC3—C3—C10—H2C10	−18.6
H1O1—O1—C2—C3	161.4	C3—C4—C5—C6	−72.0 (2)
H1O1—O1—C2—C14	43.6	C3—C4—C5—C9	50.0 (2)
C8—C1—C2—O1	−53.4 (2)	C3—C4—C5—HC5	168.0
C8—C1—C2—C3	66.3 (2)	H1C4—C4—C5—C6	49.0
C8—C1—C2—C14	−171.4 (2)	H1C4—C4—C5—C9	171.0
C9—C1—C2—O1	−177.7 (2)	H1C4—C4—C5—HC5	−71.0
C9—C1—C2—C3	−58.0 (2)	H2C4—C4—C5—C6	167.0
C9—C1—C2—C14	64.3 (2)	H2C4—C4—C5—C9	−71.0
HC1—C1—C2—O1	65.9	H2C4—C4—C5—HC5	47.0
HC1—C1—C2—C3	−174.4	C4—C5—C6—O2	−100.9 (2)
HC1—C1—C2—C14	−52.1	C4—C5—C6—C7	78.6 (2)
C2—C1—C8—C7	−85.4 (2)	C9—C5—C6—O2	135.4 (2)
C2—C1—C8—H1C8	35.7	C9—C5—C6—C7	−45.1 (2)
C2—C1—C8—H2C8	153.4	HC5—C5—C6—O2	19.1
C9—C1—C8—C7	39.9 (2)	HC5—C5—C6—C7	−161.4
C9—C1—C8—H1C8	161.0	C4—C5—C9—C1	−57.7 (2)
C9—C1—C8—H2C8	−81.3	C4—C5—C9—H1C9	62.2
HC1—C1—C8—C7	155.3	C4—C5—C9—H2C9	−177.5
HC1—C1—C8—H1C8	−83.6	C6—C5—C9—C1	68.0 (2)
HC1—C1—C8—H2C8	34.1	C6—C5—C9—H1C9	−172.2
C2—C1—C9—C5	62.6 (2)	C6—C5—C9—H2C9	−51.9
C2—C1—C9—H1C9	−57.2	HC5—C5—C9—C1	−175.7
C2—C1—C9—H2C9	−177.5	HC5—C5—C9—H1C9	−55.8
C8—C1—C9—C5	−65.6 (2)	HC5—C5—C9—H2C9	64.5
C8—C1—C9—H1C9	174.6	O2—C6—C7—C8	−160.0 (2)
C8—C1—C9—H2C9	54.3	O2—C6—C7—C12	70.7 (2)
HC1—C1—C9—C5	179.0	O2—C6—C7—HC7	−42.4
HC1—C1—C9—H1C9	59.2	C5—C6—C7—C8	20.5 (3)
HC1—C1—C9—H2C9	−61.1	C5—C6—C7—C12	−108.8 (2)
O1—C2—C3—C4	167.3 (2)	C5—C6—C7—HC7	138.1
O1—C2—C3—C10	34.0 (2)	C6—C7—C8—C1	−17.6 (3)
O1—C2—C3—HC3	−80.6	C6—C7—C8—H1C8	−138.8
C1—C2—C3—C4	46.6 (2)	C6—C7—C8—H2C8	103.6
C1—C2—C3—C10	−86.8 (2)	C12—C7—C8—C1	108.2 (2)
C1—C2—C3—HC3	158.7	C12—C7—C8—H1C8	−13.0
C14—C2—C3—C4	−75.8 (2)	C12—C7—C8—H2C8	−130.7
C14—C2—C3—C10	150.8 (2)	HC7—C7—C8—C1	−135.2
C14—C2—C3—HC3	36.2	HC7—C7—C8—H1C8	103.6
O1—C2—C14—H1C14	180.0	HC7—C7—C8—H2C8	−14.0
O1—C2—C14—H2C14	−60.0	C6—C7—C12—C11	45.4 (2)
O1—C2—C14—H3C14	60.0	C6—C7—C12—H1C12	166.2
C1—C2—C14—H1C14	−61.1	C6—C7—C12—H2C12	−75.4
C1—C2—C14—H2C14	58.9	C8—C7—C12—C11	−84.9 (2)
C1—C2—C14—H3C14	178.9	C8—C7—C12—H1C12	35.9
C3—C2—C14—H1C14	63.4	C8—C7—C12—H2C12	154.3
C3—C2—C14—H2C14	−176.6	HC7—C7—C12—C11	158.4
C3—C2—C14—H3C14	−56.6	HC7—C7—C12—H1C12	−80.8
C2—C3—C4—C5	−43.4 (2)	HC7—C7—C12—H2C12	37.6
C2—C3—C4—H1C4	−164.4	C3—C10—C11—C12	−80.0 (3)
C2—C3—C4—H2C4	77.6	C3—C10—C11—C13	102.6 (3)
C10—C3—C4—C5	91.0 (2)	H1C10—C10—C11—C12	41.4
C10—C3—C4—H1C4	−30.0	H1C10—C10—C11—C13	−136.0
C10—C3—C4—H2C4	−148.0	H2C10—C10—C11—C12	158.7
HC3—C3—C4—C5	−155.5	H2C10—C10—C11—C13	−18.7
HC3—C3—C4—H1C4	83.5	C10—C11—C12—C7	63.8 (3)
HC3—C3—C4—H2C4	−34.5	C10—C11—C12—H1C12	−57.0
C2—C3—C10—C11	105.5 (2)	C10—C11—C12—H2C12	−175.4
C2—C3—C10—H1C10	−15.8	C13—C11—C12—C7	−118.7 (2)
C2—C3—C10—H2C10	−133.1	C13—C11—C12—H1C12	120.5
C4—C3—C10—C11	−26.4 (3)	C13—C11—C12—H2C12	2.1
C4—C3—C10—H1C10	−147.8	C10—C11—C13—H1C13	0.0
C4—C3—C10—H2C10	94.9	C10—C11—C13—H2C13	−180.0
HC3—C3—C10—C11	−139.9	C12—C11—C13—H1C13	−177.4
HC3—C3—C10—H1C10	98.7	C12—C11—C13—H2C13	2.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2ⁱ	1.00	1.87	2.867 (4)	180

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₂₀O₂
M_r	220.3
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	7.554 (3), 13.196 (3), 12.597 (5)
β (°)	108.16 (2)
V (Å³)	1193.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2247, 2079, 1296
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.052, 1.27
No. of reflections	2079
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.28

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), SIR92 (Altomare et al., 1994), RAELS (Rae, 2000), ORTEPII (Johnson, 1976) and CrystalMaker (Palmer, 2005), local programs.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2ⁱ	1.00	1.87	2.867 (4)	180

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Acknowledgements

This research was supported by the Australian Research Council and the Shanghai Pujiang Program (WY).

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Palmer, D. (2005). CrystalMaker. CrystalMaker Software Ltd, Yarnton, Oxfordshire, England. http://www.CrystalMaker.co.uk. Google Scholar
Rae, A. D. (2000). RAELS. Australian National University, Canberra, Australia. Google Scholar
Yue, W., Bishop, R., Craig, D. C. & Scudder, M. L. (2000). Tetrahedron, 56, 6667–6673. Web of Science CSD CrossRef CAS Google Scholar
Yue, W., Bishop, R., Craig, D. C. & Scudder, M. L. (2002). CrystEngComm, 4, 591–595. Web of Science CSD CrossRef CAS Google Scholar
Yue, W., Bishop, R., Craig, D. C. & Scudder, M. L. (2007). Acta Cryst. E63, o4689. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yue, W., Bishop, R., Scudder, M. L. & Craig, D. C. (1997). J. Chem. Soc. Perkin Trans. 1, pp. 2937–2946. CSD CrossRef Web of Science Google Scholar
Yue, W., Nakano, K., Bishop, R., Craig, D. C., Harris, K. D. M. & Scudder, M. L. (2006). CrystEngComm, 8, 250–256. Web of Science CSD CrossRef CAS Google Scholar