(1R*,3S*,8S*)-2,2-Difluoro-3,8-dihydr­oxy-5,5-dimethyl­cyclo­oct-4(Z)-en-1-yl N,N-diethyl­carbamate

Fawcett, J.; Percy, J.M.; Pintat, S.; Smith, C.A.; Uneyama, E.

doi:10.1107/S1600536805024840

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 61| Part 10| October 2005| Pages o3322-o3323

doi:10.1107/S1600536805024840

(1R,3S,8S*)-2,2-Difluoro-3,8-dihydroxy-5,5-dimethylcyclooct-4(Z)-en-1-yl N,N-diethylcarbamate

John Fawcett,^a Jonathan M Percy,^a Stéphane Pintat,^b Clive A. Smith ^c and Emi Uneyama ^a ^*

^aDepartment of Chemistry, University of Leicester, Leicester LE1 7RH, England, ^bGlaxoSmithKline Pharmaceuticals, New Frontiers Science Park, Third Avenue, Harlow CM19 5AW, England, and ^cChroma Therapeutics Ltd, 93 Milton Park, Abingdon, Oxon OX14 4RY, England
^*Correspondence e-mail: jmp29@leicester.ac.uk

(Received 11 July 2005; accepted 3 August 2005; online 21 September 2005)

The structure of the title compound, C₁₅H₂₅F₂NO₄, is presented. Comparison of this minor product with the isomeric major product of the synthesis is made in the previous paper.

Comment

The pseudorotational relationship between the ring conformations of the title compound, (2), and diol (1), which was presented in the previous paper (Fawcett et al., 2005 ), are discussed in the Comment of that paper.

Hydrogen bonding (Table 1) links molecules of (2) into sheets perpendicular to the c axis.

Figure 1
The molecular structure of (2), showing the atom-numbering scheme and 50% displacement ellipsoids. H atoms have been omitted.

Experimental

Compound (2) was obtained as the minor product during the preparation of diol (1), as described in the previous paper (Fawcett et al., 2005). A sample was recrystallized by vapour diffusion (ethyl acetate/light petroleum) to afford colourless crystals.

Crystal data

C₁₅H₂₅F₂NO₄
M_r = 321.36
Monoclinic, P 2₁ /c
a = 20.062 (14) Å
b = 6.433 (4) Å
c = 12.424 (9) Å
β = 97.346 (12)°
V = 1590.4 (19) Å³
Z = 4
D_x = 1.342 Mg m⁻³
Mo Kα radiation
Cell parameters from 3558 reflections
θ = 3.1–28.1°
μ = 0.11 mm⁻¹
T = 150 (2) K
Block, colourless
0.28 × 0.22 × 0.15 mm

Data collection

Bruker APEX CCD area-detector diffractometer
φ and ω scans
Absorption correction: none
10968 measured reflections
2805 independent reflections
2413 reflections with I > 2σ(I)
R_int = 0.068
θ_max = 25.0°
h = −23 → 23
k = −7 → 7
l = −14 → 14

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.095
S = 1.05
2805 reflections
205 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.045P)² + 0.1172P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.003
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4ⁱ	0.84	1.92	2.7598 (19)	173
O2—H2⋯O1ⁱⁱ	0.84	2.01	2.827 (2)	163
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

H atoms were positioned geometrically, with C—H = 0.95–1.00 Å and O—H = 0.84 Å, and treated as riding, with U_iso(H) = 1.2 or 1.5 (methyl and OH) times U_eq of the parent atom.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks 2, global. DOI: 10.1107/S1600536805024840/cf6443sup1.cif

Structure factors: contains datablock 2. DOI: 10.1107/S1600536805024840/cf64432sup2.hkl

Comment top

Hydrogen bonding (Table 1) links molecules of (2) into sheets perpendicular to the c axis.

Experimental top

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. The molecular structure of (2), showing the atom-numbering scheme and 50% displacement ellipsoids.

(1R*,3S*,8S*)-2,2-Difluoro-3,8-dihydroxy-5,5-dimethylcyclooct-4(Z)-en-1-yl N,N-diethylcarbamate top

Crystal data top

C₁₅H₂₅F₂NO₄	F(000) = 688
M_r = 321.36	D_x = 1.342 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3558 reflections
a = 20.062 (14) Å	θ = 3.1–28.1°
b = 6.433 (4) Å	µ = 0.11 mm⁻¹
c = 12.424 (9) Å	T = 150 K
β = 97.346 (12)°	Block, colourless
V = 1590.4 (19) Å³	0.28 × 0.22 × 0.15 mm
Z = 4

Data collection top

Bruker APEX CCD area-detector diffractometer	2413 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.068
Graphite monochromator	θ_max = 25.0°, θ_min = 2.1°
ϕ and ω scans	h = −23→23
10968 measured reflections	k = −7→7
2805 independent reflections	l = −14→14

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.045P)² + 0.1172P] where P = (F_o² + 2F_c²)/3
2805 reflections	(Δ/σ)_max = 0.003
205 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₅H₂₅F₂NO₄	V = 1590.4 (19) Å³
M_r = 321.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 20.062 (14) Å	µ = 0.11 mm⁻¹
b = 6.433 (4) Å	T = 150 K
c = 12.424 (9) Å	0.28 × 0.22 × 0.15 mm
β = 97.346 (12)°

Data collection top

Bruker APEX CCD area-detector diffractometer	2413 reflections with I > 2σ(I)
10968 measured reflections	R_int = 0.068
2805 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.05	Δρ_max = 0.22 e Å⁻³
2805 reflections	Δρ_min = −0.21 e Å⁻³
205 parameters

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
F1	0.17709 (4)	0.50429 (15)	0.94617 (7)	0.0317 (3)
F2	0.23221 (4)	0.25700 (13)	0.87715 (7)	0.0289 (2)
N1	0.11443 (6)	0.73451 (19)	0.64634 (10)	0.0253 (3)
O1	0.25363 (6)	0.30397 (16)	1.10013 (8)	0.0279 (3)
H1	0.2329	0.3768	1.1410	0.042*
O2	0.30629 (6)	0.58984 (17)	0.66659 (8)	0.0274 (3)
H2	0.2857	0.4869	0.6370	0.041*
O3	0.19811 (5)	0.58723 (15)	0.75457 (8)	0.0234 (3)
O4	0.19503 (5)	0.93651 (16)	0.73795 (8)	0.0269 (3)
C1	0.28505 (8)	0.4356 (2)	1.02965 (12)	0.0228 (4)
H1A	0.2908	0.5774	1.0625	0.027*
C2	0.23950 (7)	0.4496 (2)	0.92154 (12)	0.0220 (3)
C3	0.25589 (7)	0.6030 (2)	0.83486 (11)	0.0205 (3)
H3	0.2589	0.7468	0.8657	0.025*
C4	0.31992 (8)	0.5554 (2)	0.78015 (12)	0.0226 (3)
H4	0.3315	0.4054	0.7923	0.027*
C5	0.38220 (7)	0.6860 (2)	0.82212 (12)	0.0247 (4)
C6	0.39729 (8)	0.6690 (3)	0.94646 (12)	0.0272 (4)
H6A	0.4400	0.7420	0.9708	0.033*
H6B	0.3612	0.7399	0.9797	0.033*
C7	0.40263 (8)	0.4506 (3)	0.98573 (13)	0.0295 (4)
H7	0.4447	0.3823	0.9870	0.035*
C8	0.35268 (8)	0.3461 (3)	1.01882 (12)	0.0269 (4)
H8	0.3601	0.2038	1.0371	0.032*
C9	0.17114 (8)	0.7665 (2)	0.71366 (12)	0.0213 (3)
C10	0.09080 (8)	0.5314 (2)	0.60752 (13)	0.0302 (4)
H10C	0.0413	0.5259	0.6044	0.036*
H10D	0.1101	0.4239	0.6594	0.036*
C11	0.10994 (10)	0.4840 (3)	0.49671 (15)	0.0404 (5)
H11D	0.0923	0.5928	0.4457	0.061*
H11E	0.0910	0.3494	0.4718	0.061*
H11F	0.1590	0.4789	0.5006	0.061*
C5"	0.37228 (8)	0.9155 (2)	0.79324 (13)	0.0313 (4)
H5"1	0.4109	0.9954	0.8274	0.047*
H5"2	0.3312	0.9661	0.8194	0.047*
H5"3	0.3684	0.9323	0.7143	0.047*
C5'	0.44161 (8)	0.6016 (3)	0.77064 (14)	0.0362 (4)
H5'1	0.4334	0.6213	0.6918	0.054*
H5'2	0.4471	0.4531	0.7870	0.054*
H5'3	0.4826	0.6760	0.8000	0.054*
C10'	0.07636 (8)	0.9164 (3)	0.60459 (13)	0.0293 (4)
H10A	0.0514	0.8827	0.5328	0.035*
H10B	0.1080	1.0308	0.5945	0.035*
C11'	0.02753 (9)	0.9882 (3)	0.67924 (15)	0.0388 (4)
H11A	−0.0045	0.8765	0.6883	0.058*
H11B	0.0032	1.1105	0.6480	0.058*
H11C	0.0521	1.0243	0.7501	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0218 (5)	0.0425 (6)	0.0322 (5)	0.0031 (4)	0.0085 (4)	0.0033 (4)
F2	0.0379 (6)	0.0228 (5)	0.0260 (5)	−0.0057 (4)	0.0036 (4)	−0.0032 (4)
N1	0.0254 (7)	0.0247 (7)	0.0240 (7)	0.0031 (5)	−0.0035 (6)	0.0010 (5)
O1	0.0360 (7)	0.0256 (6)	0.0239 (6)	0.0017 (5)	0.0103 (5)	0.0029 (5)
O2	0.0351 (7)	0.0288 (6)	0.0183 (6)	−0.0051 (5)	0.0033 (5)	−0.0025 (5)
O3	0.0223 (6)	0.0212 (6)	0.0245 (6)	−0.0004 (4)	−0.0047 (4)	−0.0001 (4)
O4	0.0336 (6)	0.0208 (6)	0.0256 (6)	−0.0015 (5)	0.0014 (5)	−0.0010 (5)
C1	0.0275 (9)	0.0207 (8)	0.0206 (8)	−0.0006 (6)	0.0048 (6)	0.0007 (6)
C2	0.0207 (8)	0.0200 (8)	0.0261 (8)	−0.0004 (6)	0.0059 (6)	−0.0043 (6)
C3	0.0194 (8)	0.0209 (8)	0.0198 (8)	0.0015 (6)	−0.0026 (6)	−0.0022 (6)
C4	0.0272 (9)	0.0217 (8)	0.0187 (8)	−0.0001 (6)	0.0030 (6)	0.0000 (6)
C5	0.0229 (8)	0.0267 (9)	0.0246 (8)	−0.0010 (7)	0.0029 (6)	−0.0002 (7)
C6	0.0201 (8)	0.0337 (9)	0.0267 (9)	−0.0033 (7)	−0.0011 (7)	0.0005 (7)
C7	0.0231 (9)	0.0373 (10)	0.0268 (9)	0.0054 (7)	−0.0010 (7)	0.0035 (7)
C8	0.0301 (9)	0.0272 (9)	0.0224 (8)	0.0062 (7)	0.0000 (7)	0.0036 (7)
C9	0.0249 (8)	0.0229 (9)	0.0170 (7)	0.0022 (6)	0.0058 (6)	0.0006 (6)
C10	0.0259 (9)	0.0295 (9)	0.0329 (9)	−0.0039 (7)	−0.0049 (7)	0.0017 (7)
C11	0.0435 (11)	0.0362 (10)	0.0392 (11)	0.0071 (9)	−0.0028 (9)	−0.0101 (8)
C5"	0.0304 (9)	0.0305 (9)	0.0316 (9)	−0.0067 (7)	−0.0004 (7)	0.0028 (7)
C5'	0.0285 (9)	0.0458 (11)	0.0357 (10)	−0.0012 (8)	0.0098 (8)	0.0024 (8)
C10'	0.0305 (9)	0.0324 (9)	0.0242 (9)	0.0080 (7)	0.0008 (7)	0.0038 (7)
C11'	0.0407 (11)	0.0425 (11)	0.0342 (10)	0.0126 (9)	0.0087 (8)	0.0031 (8)

Geometric parameters (Å, º) top

F1—C2	1.3722 (18)	C6—H6A	0.990
F2—C2	1.3564 (18)	C6—H6B	0.990
N1—C9	1.339 (2)	C7—C8	1.316 (2)
N1—C10	1.451 (2)	C7—H7	0.950
N1—C10'	1.456 (2)	C8—H8	0.950
O1—C1	1.4220 (18)	C10—C11	1.507 (3)
O1—H1	0.840	C10—H10C	0.990
O2—C4	1.420 (2)	C10—H10D	0.990
O2—H2	0.840	C11—H11D	0.980
O3—C9	1.3458 (19)	C11—H11E	0.980
O3—C3	1.4329 (18)	C11—H11F	0.980
O4—C9	1.2167 (19)	C5"—H5"1	0.980
C1—C8	1.496 (2)	C5"—H5"2	0.980
C1—C2	1.528 (2)	C5"—H5"3	0.980
C1—H1A	1.000	C5'—H5'1	0.980
C2—C3	1.527 (2)	C5'—H5'2	0.980
C3—C4	1.559 (2)	C5'—H5'3	0.980
C3—H3	1.000	C10'—C11'	1.505 (2)
C4—C5	1.540 (2)	C10'—H10A	0.990
C4—H4	1.000	C10'—H10B	0.990
C5—C5'	1.523 (2)	C11'—H11A	0.980
C5—C5"	1.526 (2)	C11'—H11B	0.980
C5—C6	1.540 (2)	C11'—H11C	0.980
C6—C7	1.487 (2)

C9—N1—C10	124.15 (13)	C6—C7—H7	118.0
C9—N1—C10'	117.66 (13)	C7—C8—C1	124.56 (15)
C10—N1—C10'	118.09 (13)	C7—C8—H8	117.7
C1—O1—H1	109.5	C1—C8—H8	117.7
C4—O2—H2	109.5	O4—C9—N1	124.71 (14)
C9—O3—C3	116.91 (12)	O4—C9—O3	123.38 (14)
O1—C1—C8	107.74 (13)	N1—C9—O3	111.89 (13)
O1—C1—C2	108.30 (13)	N1—C10—C11	112.04 (14)
C8—C1—C2	113.03 (13)	N1—C10—H10C	109.2
O1—C1—H1A	109.2	C11—C10—H10C	109.2
C8—C1—H1A	109.2	N1—C10—H10D	109.2
C2—C1—H1A	109.2	C11—C10—H10D	109.2
F2—C2—F1	105.72 (12)	H10C—C10—H10D	107.9
F2—C2—C3	108.99 (12)	C10—C11—H11D	109.5
F1—C2—C3	106.05 (12)	C10—C11—H11E	109.5
F2—C2—C1	108.96 (12)	H11D—C11—H11E	109.5
F1—C2—C1	106.22 (12)	C10—C11—H11F	109.5
C3—C2—C1	119.96 (13)	H11D—C11—H11F	109.5
O3—C3—C2	102.53 (12)	H11E—C11—H11F	109.5
O3—C3—C4	108.72 (12)	C5—C5"—H5"1	109.5
C2—C3—C4	116.38 (12)	C5—C5"—H5"2	109.5
O3—C3—H3	109.6	H5"1—C5"—H5"2	109.5
C2—C3—H3	109.6	C5—C5"—H5"3	109.5
C4—C3—H3	109.6	H5"1—C5"—H5"3	109.5
O2—C4—C5	107.23 (12)	H5"2—C5"—H5"3	109.5
O2—C4—C3	109.75 (12)	C5—C5'—H5'1	109.5
C5—C4—C3	115.04 (12)	C5—C5'—H5'2	109.5
O2—C4—H4	108.2	H5'1—C5'—H5'2	109.5
C5—C4—H4	108.2	C5—C5'—H5'3	109.5
C3—C4—H4	108.2	H5'1—C5'—H5'3	109.5
C5'—C5—C5"	109.39 (13)	H5'2—C5'—H5'3	109.5
C5'—C5—C6	109.39 (13)	N1—C10'—C11'	112.35 (14)
C5"—C5—C6	107.91 (13)	N1—C10'—H10A	109.1
C5'—C5—C4	107.92 (14)	C11'—C10'—H10A	109.1
C5"—C5—C4	111.86 (13)	N1—C10'—H10B	109.1
C6—C5—C4	110.35 (12)	C11'—C10'—H10B	109.1
C7—C6—C5	113.14 (13)	H10A—C10'—H10B	107.9
C7—C6—H6A	109.0	C10'—C11'—H11A	109.5
C5—C6—H6A	109.0	C10'—C11'—H11B	109.5
C7—C6—H6B	109.0	H11A—C11'—H11B	109.5
C5—C6—H6B	109.0	C10'—C11'—H11C	109.5
H6A—C6—H6B	107.8	H11A—C11'—H11C	109.5
C8—C7—C6	124.04 (15)	H11B—C11'—H11C	109.5
C8—C7—H7	118.0

O1—C1—C2—F2	−61.47 (15)	C3—C4—C5—C5"	−66.51 (17)
C8—C1—C2—F2	57.83 (16)	O2—C4—C5—C6	176.01 (12)
O1—C1—C2—F1	52.00 (15)	C3—C4—C5—C6	53.64 (17)
C8—C1—C2—F1	171.30 (12)	C5'—C5—C6—C7	−65.68 (17)
O1—C1—C2—C3	172.00 (12)	C5"—C5—C6—C7	175.41 (13)
C8—C1—C2—C3	−68.70 (18)	C4—C5—C6—C7	52.91 (17)
C9—O3—C3—C2	134.44 (12)	C5—C6—C7—C8	−95.27 (19)
C9—O3—C3—C4	−101.78 (14)	C6—C7—C8—C1	−4.8 (3)
F2—C2—C3—O3	60.55 (14)	O1—C1—C8—C7	−160.47 (15)
F1—C2—C3—O3	−52.85 (14)	C2—C1—C8—C7	79.9 (2)
C1—C2—C3—O3	−172.94 (12)	C10—N1—C9—O4	172.08 (14)
F2—C2—C3—C4	−57.97 (16)	C10'—N1—C9—O4	−4.1 (2)
F1—C2—C3—C4	−171.36 (11)	C10—N1—C9—O3	−9.8 (2)
C1—C2—C3—C4	68.55 (18)	C10'—N1—C9—O3	174.05 (12)
O3—C3—C4—O2	22.24 (16)	C3—O3—C9—O4	3.3 (2)
C2—C3—C4—O2	137.32 (13)	C3—O3—C9—N1	−174.85 (12)
O3—C3—C4—C5	143.24 (12)	C9—N1—C10—C11	−97.16 (18)
C2—C3—C4—C5	−101.68 (16)	C10'—N1—C10—C11	78.99 (18)
O2—C4—C5—C5'	−64.51 (16)	C9—N1—C10'—C11'	−87.16 (18)
C3—C4—C5—C5'	173.12 (13)	C10—N1—C10'—C11'	96.43 (18)
O2—C4—C5—C5"	55.86 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.84	1.92	2.7598 (19)	173
O2—H2···O1ⁱⁱ	0.84	2.01	2.827 (2)	163

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₂₅F₂NO₄
M_r	321.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	20.062 (14), 6.433 (4), 12.424 (9)
β (°)	97.346 (12)
V (Å³)	1590.4 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.28 × 0.22 × 0.15

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10968, 2805, 2413
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.095, 1.05
No. of reflections	2805
No. of parameters	205
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.21

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 2000), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.84	1.92	2.7598 (19)	173
O2—H2···O1ⁱⁱ	0.84	2.01	2.827 (2)	163

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+1/2, z−1/2.

Acknowledgements

The authors thank the Universities of Birmingham and Leicester, the EPSRC (project prant GR/K84882 for SP), GlaxoSmithKline (CASE studentship for SP) and Universities UK (ORS Award for EU).

References

Bruker (1997). SMART. Version 5.622. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Version 6.02. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fawcett, J., Percy, J. M., Pintat, S., Smith, C. A. & Uneyama, E. (2005). Acta Cryst. E61, o3319–o3321. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2000). SHELXTL. Version 6.10. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar

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ISSN: 2056-9890

Volume 61| Part 10| October 2005| Pages o3322-o3323

doi:10.1107/S1600536805024840

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

(1R*,3S*,8S*)-2,2-Di­fluoro-3,8-dihydr­­oxy-5,5-di­methyl­cyclo­oct-4(Z)-en-1-yl N,N-di­ethyl­carbamate

Comment

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(1R,3S,8S*)-2,2-Difluoro-3,8-dihydroxy-5,5-dimethylcyclooct-4(Z)-en-1-yl N,N-diethylcarbamate