# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2003

(1Z)-3,4-anti-1-Chloro-4-hydroxy-5-methyl-3-phenylsulfonylhex-1-ene

1
Contact Name
Dr David H. Grayson,
University Chemical Laboratory,
Trinity College,
Dublin 2,
Ireland
2
Contact e-mail address
dgrayson@tcd.ie

3
Authors' names
Sylvia M. Draper, Eva. T. Gallagher, David H. Grayson
4
Journal
Journal of Organic and Biological Chemistry
5
Compound name
(1Z)-3,4-anti-1-Chloro-4-hydroxy-5-methyl-3-
phenylsulfonylhex-1-ene
6
Compound synonym
n/a
7
Formula
C13H17 Cl1O3S

8
Formula weight
288.78

9
Colour
Colourless

10
Melting point K
379 K
11
Crystal habit
Triclinic

12
Crystallisation solvent
Diethyl ether/n-pentane

13
Unit Cell parameters
a = 8.4685(9), b = 8.7296(9), c = 11.4820(13) Å
? = 86.140(9)o, ? = 73.644(9)o, ? = 61.328(8)o 

14
Unit Cell volume
V = 712.29(13) Å3

15
Space Group
P-1

16
Z value
2

17
Calculated density
1.346 g cm3

18
Temperature of study
293(2) K

19
R factor
0.0549

20
Atomic coordinates
Table 1
21
Atomic displacement 
parameters
Table 2
22
Bond lengths
Table 3
23
Bond angles
Table 3
24
Torsion angles
n/a




Table 1

Atomic coordinates (x 104) and equivalent isotropic displacement parameters (Å2 x 103) for 
(1Z)-3,4-anti-1-Chloro-4-hydroxy-5-methyl-3-phenylsulfonylhex-1-ene.
U(eq) is defined as one third of the trace of the orthogonalized Uij tensor.
                                                            
                                                            
  Atom
  x
  y
  z
 U(eq)
                             




S(1)
3112(1)
2188(1)
8132(1)
40(1)
Cl(1)
8153(1)
2542(1)
6551(1)
86(1)
O(1)
1857(2)
2664(2)
7393(2)
57(1)
O(2)
2423(2)
2014(2)
9401(1)
53(1)
O(3)
1593(3)
5789(2)
9627(2)
63(1)
C(1)
5132(3)
 171(3)
7502(2)
40(1)
C(2)
5935(4)
–109(3)
6257(2)
55(1)
C(3)
7467(4)
–1719(4)
5775(3)
69(1)
C(4)
8152(4)
–3018(4)
6531(3)
66(1)
C(5)
7349(4)
–2728(3)
7765(3)
60(1)
C(6)
5829(3)
–1129(3)
8260(2)
49(1)
C(7)
7127(4)
2984(3)
8095(3)
58(1)
C(8)
5353(3)
3379(3)
8606(2)
44(1)
C(9)
3921(3)
3787(3)
7952(2)
38(1)
C(10)
2216(3)
5622(3)
8335(2)
42(1)
C(11)
2683(3)
7063(3)
7829(2)
53(1)
C(12)
990(5)
8840(4)
8314(5)
86(1)
C(13)
3324(9)
6927(6)
6464(4)
99(1)
                                   
 



  
Table 2

Anisotropic displacement parameters (Å2 x 103) for (1Z)-3,4-anti-1-Chloro-4-hydroxy-5-methyl-
3-phenylsulfonylhex-1-ene. 
The anistropic displacement factor exponent takes the form:  
–2?2[h2 a*2 U11 + …… +  2 h k a* b* U12]
                                                            
                                                            
  Atom
U11
U22
U33
U23
U13
U12
                             






S(1)
37(1)
42(1)
42(1)
3(1)
–9(1)
–20(1)
Cl(1)
46(1)
121(1)
83(1)
–3(1)
–2(1)
–41(1)
O(1)
51(1)
57(1)
72(1)
6(1)
–30(1)
–27(1)
O(2)
51(1)
51(1)
46(1)
4(1)
2(1)
–24(1)
O(3)
52(1)
58(1)
50(1)
—3(1)
1(1)
–12(1)
C(1)
39(1)
42(1)
43(1)
—2(1)
–9(1)
–22(1)
C(2)
58(1)
61(2)
44(2)
1(1)
–10(1)
–29(1)
C(3)
59(2)
83(2)
53(2)
—21(1)
4(1)
–34(2)
C(4)
47(1)
55(2)
86(2)
—19(1)
–13(1)
–17(1)
C(5)
53(1)
48(1)
78(2)
2(1)
–24(1)
–20(1)
C(6)
50(1)
47(1)
49(1)
2(1)
–14(1)
–23(1)
C(7)
48(1)
55(1)
77(2)
2(1)
–29(1)
–22(1)
C(8)
44(1)
43(1)
48(1)
3(1)
–19(1)
–19(1)
C(9)
36(1)
41(1)
36(1)
3(1)
–8(1)
–20(1)
C(10)
37(1)
44(1)
45(1)
4(1)
–12(1)
–19(1)
C(11)
48(1)
45(1)
71(2)
9(1)
–19(1)
–25(1)
C(12)
80(2)
41(2)
124(3)
4(2)
12(2)
–27(2)
C(13)
134(4)
70(2)
77(2)
25(2)
–5(3)
–52(3)
























Table 3

Bond lengths [Å] and angles [o] for (1Z)-3,4-anti-1-Chloro-4-hydroxy-5-methyl-3-
phenylsulfonylhex-1-ene.
 
S(1)-O(1)
1.435(2)
C(5)-C(6)
1.378(3)
S(1)-O(2)
1.436(2)
C(7)-C(8)
1.307(3)
S(1)-C(1)
1.771(2)
C(8)-C(9)
1.490(3)
S(1)-C(9)
1.806(2)
C(9)-C(10)
1.536(3)
Cl(1)-C(7)
1.715(3)
C(10)-C(11)
1.525(3)
O(3)-C(10)
1.420(3)
C(11)-C(13)
1.500(5)
C(1)-C(2)
1.380(3)
C(11)-C(12)
1.518(4)
C(1)-C(6)
1.381(3)


C(2)-C(3)
1.384(4)


C(3)-C(4)
1.377(4)


C(4)-C(5)
1.369(4)


                                         



O(1)-S(1)-0(2)
117.96(10)
C(8)-C(7)-Cl(1)
123.8(2)
O(1)-S(1)-C(1)
108.57(10)
C(7)-C(8)-C(9)
125.8(2)
O(2)-S(1)-C(1)
107.40(10)
C(8)-C(9)-C(10)
113.1(2)
O(1)-S(1)-C(9)
106.52(9)
C(8)-C(9)-S(1)
112.33(14)
O(2)-S(1)-C(9)
110.26(10)
C(10)-C(9)-S(1)
108.99(14)
C(1)-S(1)-C(9)
105.45(9)
O(3)-C(10)-C(11)
111.8(2)
C(2)-C(1)-C(6)
121.0(2)
O(3)-C(10)-C(9)
106.9(2)
C(2)-C(1)-S(1)
119.6(2)
C(11)-C(10)-C(9)
112.1(2)
C(6)-C(1)-S(1)
119.4(2)
C(13)-C(11)-C(12)
110.6(3)
C(1)-C(2)-C(3)
118.9(2)
C(13)-C(11)-C(10)
112.9(3)
C(4)-C(3)-C(2)
120.1(3)
C(12)-C(11)-C(10)
109.5(2)
C(5)-C(4)-C(3)
120.7(2)


C(4)-C(5)-C(6)
119.9(3)


C(5)-C(6)-C(1)
119.5(2)