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

data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Steven V. Ley'
'Christopher J. Hollowood'

_publ_contact_author_name        'Prof Steven V Ley'
_publ_contact_author_address     
;
Department of Chemistry
University of Cambridge
Lensfield Road
Cambridge
CB2 1EW
UNITED KINGDOM
;

_publ_contact_author_email       SVL1000@CAM.AC.UK

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
Reductive decomplexation of p-allyltricarbonyliron
lactone complexes using sodium naphthalenide as a route to stereodefined
1,7-diols and 2,3-diene-1,7-diols
;

data_CRYSTALS_cif
_database_code_CSD               213234
#=============================================================
# Diffractometer details
#=============================================================
_diffrn_measurement_device_type  
;
Nonius KappaCCD
;
_diffrn_radiation_monochromator  graphite
_computing_data_collection       
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction        
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_cell_refinement       
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
#=============================================================
# General computing
#=============================================================
_computing_structure_refinement  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_publication_material  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'

_chemical_name_systematic        # IUPAC name, in full
;
?
;
_chemical_melting_point          'not measured'
_refine_ls_matrix_type           full
_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_chemical_absolute_configuration rmad
#=============================================================
_cell_length_a                   10.7470(3)
_cell_angle_alpha                90
_cell_length_b                   8.3113(2)
_cell_angle_beta                 100.4321(12)
_cell_length_c                   13.5613(4)
_cell_angle_gamma                90
_cell_volume                     1191.3
_symmetry_cell_setting           'Monoclinic '
_symmetry_space_group_name_H-M   'P 1 21 1 '

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C   ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'H   ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997
0.0030 International_Tables_Vol_IV_Table_2.2B
'O   ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 International_Tables_Vol_IV_Table_2.2B
'S   ' 0.1100 0.1240 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 International_Tables_Vol_IV_Table_2.2B
_chemical_formula_sum            ' C20 H24 O11 S2 '
_chemical_formula_moiety         ' C20 H24 O11 S2 '
_chemical_compound_source        
;
synthesis as described
;
_chemical_formula_weight         504.52
_cell_measurement_reflns_used    10203
_cell_measurement_theta_min      5
_cell_measurement_theta_max      28
_cell_measurement_temperature    200
_cell_formula_units_Z            2
_exptl_crystal_description       ' fragment '
_exptl_crystal_colour            ' colourless '
_exptl_crystal_size_min          0.28
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_max          0.40
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_F_000             528.648
_exptl_absorpt_coefficient_mu    0.280
_diffrn_measurement_method       \w
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.92
_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0.00
_diffrn_ambient_temperature      200
_diffrn_reflns_number            10203
_reflns_number_total             4755
#4759 unique reflections including systematic absences
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_gt                3881
_diffrn_reflns_theta_min         5.10
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -13
_reflns_limit_h_max              13
_reflns_limit_k_min              -9
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              17
_refine_diff_density_min         -0.40
_refine_diff_density_max         0.36
_reflns_threshold_expression     >3.00\s(I)
_refine_ls_number_reflns         3881
_refine_ls_number_parameters     298
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.0465
_refine_ls_goodness_of_fit_ref   1.0631
_refine_ls_shift/su_max          0.000224
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_abs_structure_details 'Flack, 1862 Friedel-pairs'
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Chebychev polynomial with 4 parameters (Carruthers & Watkin , 1979)
2.88    -.203     1.44    0.175
;
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073

# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
O1 0.22336(17) 0.1065(2) 0.21698(13) 0.0467 1.0000 Uani
C1 0.3348(2) 0.2003(4) 0.2232(2) 0.0442 1.0000 Uani
C2 0.3256(2) 0.3445(3) 0.2911(2) 0.0402 1.0000 Uani
C3 0.3080(2) 0.2892(3) 0.39476(19) 0.0395 1.0000 Uani
C4 0.1986(2) 0.1711(3) 0.3861(2) 0.0424 1.0000 Uani
C5 0.2133(2) 0.0366(4) 0.3121(2) 0.0450 1.0000 Uani
S1 0.34526(8) 0.27211(12) 0.09878(6) 0.0558 1.0000 Uani
S2 0.39905(7) 0.05903(12) 0.03654(6) 0.0543 1.0000 Uani
O2 0.4797(2) -0.0269(3) 0.11365(19) 0.0710 1.0000 Uani
O3 0.4435(3) 0.1116(4) -0.0514(2) 0.0835 1.0000 Uani
C6 0.2598(3) -0.0526(4) -0.0006(2) 0.0493 1.0000 Uani
C7 0.2400(4) -0.1853(5) 0.0535(3) 0.0814 1.0000 Uani
C8 0.1295(5) -0.2721(7) 0.0255(4) 0.1145 1.0000 Uani
C9 0.0427(4) -0.2275(9) -0.0554(4) 0.1037 1.0000 Uani
C10 0.0640(4) -0.0956(7) -0.1100(4) 0.0911 1.0000 Uani
C11 0.1740(3) -0.0031(5) -0.0837(2) 0.0679 1.0000 Uani
O4 0.44155(15) 0.4336(2) 0.29907(14) 0.0435 1.0000 Uani
C12 0.4338(3) 0.5963(3) 0.28954(19) 0.0437 1.0000 Uani
O5 0.3351(2) 0.6669(3) 0.2788(2) 0.0657 1.0000 Uani
C13 0.5613(3) 0.6698(4) 0.2952(2) 0.0595 1.0000 Uani
O6 0.27377(15) 0.4272(2) 0.44855(14) 0.0436 1.0000 Uani
C14 0.3662(2) 0.5080(4) 0.5112(2) 0.0449 1.0000 Uani
O7 0.47348(18) 0.4613(3) 0.53123(17) 0.0585 1.0000 Uani
C15 0.3169(3) 0.6575(4) 0.5477(3) 0.0616 1.0000 Uani
O8 0.19953(17) 0.0973(3) 0.48230(14) 0.0476 1.0000 Uani
C16 0.0938(3) 0.1131(5) 0.5247(3) 0.0737 1.0000 Uani
O9 0.0049(3) 0.1897(6) 0.4872(4) 0.1434 1.0000 Uani
C17 0.1038(4) 0.0176(5) 0.6183(3) 0.0805 1.0000 Uani
C18 0.1025(3) -0.0780(4) 0.2928(2) 0.0534 1.0000 Uani
O10 -0.00972(18) 0.0183(3) 0.2596(2) 0.0743 1.0000 Uani
C19 -0.1157(3) -0.0546(5) 0.2315(3) 0.0686 1.0000 Uani
O11 -0.1203(4) -0.1949(5) 0.2331(5) 0.1885 1.0000 Uani
C20 -0.2249(3) 0.0525(7) 0.2000(3) 0.0911 1.0000 Uani
H11 0.4111 0.1345 0.2508 0.0519 1.0000 Uiso
H21 0.2512 0.4127 0.2623 0.0467 1.0000 Uiso
H31 0.3881 0.2375 0.4295 0.0464 1.0000 Uiso
H41 0.1181 0.2312 0.3625 0.0498 1.0000 Uiso
H51 0.2904 -0.0251 0.3431 0.0528 1.0000 Uiso
H71 0.3044 -0.2193 0.1126 0.0953 1.0000 Uiso
H81 0.1134 -0.3688 0.0652 0.1378 1.0000 Uiso
H91 -0.0368 -0.2913 -0.0750 0.1266 1.0000 Uiso
H101 -0.0002 -0.0644 -0.1700 0.1051 1.0000 Uiso
H111 0.1897 0.0941 -0.1231 0.0793 1.0000 Uiso
H131 0.5526 0.7892 0.2880 0.0713 1.0000 Uiso
H132 0.6150 0.6435 0.3614 0.0713 1.0000 Uiso
H133 0.6018 0.6260 0.2400 0.0713 1.0000 Uiso
H151 0.3865 0.7143 0.5935 0.0738 1.0000 Uiso
H152 0.2474 0.6311 0.5850 0.0738 1.0000 Uiso
H153 0.2834 0.7285 0.4895 0.0738 1.0000 Uiso
H171 0.0251 0.0321 0.6470 0.1002 1.0000 Uiso
H172 0.1786 0.0552 0.6679 0.1002 1.0000 Uiso
H173 0.1144 -0.0987 0.6030 0.1002 1.0000 Uiso
H181 0.0950 -0.1369 0.3558 0.0629 1.0000 Uiso
H182 0.1140 -0.1572 0.2397 0.0629 1.0000 Uiso
H201 -0.3031 -0.0137 0.1795 0.1065 1.0000 Uiso
H202 -0.2358 0.1241 0.2571 0.1065 1.0000 Uiso
H203 -0.2101 0.1197 0.1421 0.1065 1.0000 Uiso
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0440(9) 0.0447(11) 0.046(1) 0.0066(9) -0.0050(8) -0.0142(8)
C1 0.0377(12) 0.0458(16) 0.0462(14) 0.0103(12) 0.000(1) -0.0088(11)
C2 0.0292(11) 0.0402(15) 0.0474(14) 0.0063(11) -0.003(1) -0.007(1)
C3 0.0282(11) 0.0405(14) 0.0473(13) 0.0058(12) 0.0004(9) -0.002(1)
C4 0.0304(11) 0.0418(15) 0.0524(14) 0.0136(12) 0.000(1) -0.003(1)
C5 0.0378(12) 0.0415(16) 0.0528(14) 0.0144(12) 0.000(1) -0.0073(11)
S1 0.0702(5) 0.0478(4) 0.0481(4) 0.0082(3) 0.0071(3) -0.0134(4)
S2 0.0462(3) 0.0610(5) 0.0574(4) -0.0009(4) 0.0137(3) -0.0120(3)
O2 0.0482(11) 0.0721(17) 0.0843(16) -0.0057(13) -0.0100(11) 0.0039(11)
O3 0.0901(18) 0.091(2) 0.0816(17) -0.0023(15) 0.0470(14) -0.0252(16)
C6 0.0455(14) 0.0590(19) 0.0426(13) -0.0083(13) 0.0059(11) -0.0061(13)
C7 0.095(3) 0.086(3) 0.0580(19) 0.0037(19) -0.0022(18) -0.048(2)
C8 0.121(4) 0.145(5) 0.078(3) -0.025(3) 0.021(3) -0.091(4)
C9 0.065(2) 0.151(5) 0.101(3) -0.063(4) 0.030(2) -0.046(3)
C10 0.0507(19) 0.123(4) 0.089(3) -0.056(3) -0.0154(19) 0.019(2)
C11 0.0655(19) 0.075(3) 0.0572(18) -0.0176(17) -0.0037(15) 0.0179(17)
O4 0.0306(8) 0.0440(11) 0.053(1) 0.0066(9) -0.0003(7) -0.0099(7)
C12 0.0548(15) 0.0383(16) 0.0381(12) 0.0029(11) 0.0084(11) -0.0103(12)
O5 0.0635(14) 0.0457(13) 0.0880(17) 0.0102(12) 0.0141(12) 0.0000(11)
C13 0.0647(19) 0.063(2) 0.0503(16) 0.0006(15) 0.0099(14) -0.0293(16)
O6 0.0311(8) 0.0460(11) 0.052(1) -0.0011(9) 0.0033(7) -0.0034(8)
C14 0.0337(12) 0.0537(17) 0.0453(13) 0.0031(12) 0.002(1) -0.0113(11)
O7 0.038(1) 0.0632(15) 0.0672(13) -0.0030(11) -0.0089(9) -0.003(1)
C15 0.0500(16) 0.064(2) 0.070(2) -0.0129(17) 0.0103(14) -0.0089(15)
O8 0.0406(9) 0.0487(12) 0.054(1) 0.0116(9) 0.0095(8) -0.0009(8)
C16 0.0509(17) 0.085(3) 0.091(3) 0.026(2) 0.0271(17) -0.0070(18)
O9 0.0580(15) 0.218(5) 0.168(3) 0.109(3) 0.0563(19) 0.043(2)
C17 0.097(3) 0.079(3) 0.075(2) 0.015(2) 0.039(2) -0.025(2)
C18 0.0478(15) 0.0428(17) 0.0666(18) 0.0102(14) 0.0021(13) -0.0096(13)
O10 0.038(1) 0.0559(15) 0.119(2) 0.0138(14) -0.0115(11) -0.019(1)
C19 0.0589(19) 0.073(3) 0.068(2) 0.0110(18) -0.0029(15) -0.0366(18)
O11 0.109(3) 0.083(3) 0.329(7) 0.025(4) -0.078(4) -0.051(2)
C20 0.0402(15) 0.129(4) 0.097(3) 0.013(3) -0.0059(16) -0.023(2)
_refine_ls_extinction_method     None
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C1 . 1.419(3) yes
O1 . C5 . 1.437(3) yes
C1 . C2 . 1.525(4) yes
C1 . S1 . 1.812(3) yes
C1 . H11 . 1.000 no
C2 . C3 . 1.523(4) yes
C2 . O4 . 1.437(3) yes
C2 . H21 . 1.000 no
C3 . C4 . 1.520(3) yes
C3 . O6 . 1.442(3) yes
C3 . H31 . 1.000 no
C4 . C5 . 1.529(4) yes
C4 . O8 . 1.440(3) yes
C4 . H41 . 1.000 no
C5 . C18 . 1.510(4) yes
C5 . H51 . 1.000 no
S1 . S2 . 2.0880(12) yes
S2 . O2 . 1.423(3) yes
S2 . O3 . 1.431(3) yes
S2 . C6 . 1.755(3) yes
C6 . C7 . 1.362(5) yes
C6 . C11 . 1.383(4) yes
C7 . C8 . 1.383(5) yes
C7 . H71 . 1.000 no
C8 . C9 . 1.356(8) yes
C8 . H81 . 1.000 no
C9 . C10 . 1.366(8) yes
C9 . H91 . 1.000 no
C10 . C11 . 1.401(6) yes
C10 . H101 . 1.000 no
C11 . H111 . 1.000 no
O4 . C12 . 1.359(4) yes
C12 . O5 . 1.197(4) yes
C12 . C13 . 1.489(4) yes
C13 . H131 . 1.000 no
C13 . H132 . 1.000 no
C13 . H133 . 1.000 no
O6 . C14 . 1.362(3) yes
C14 . O7 . 1.200(3) yes
C14 . C15 . 1.471(5) yes
C15 . H151 . 1.000 no
C15 . H152 . 1.000 no
C15 . H153 . 1.000 no
O8 . C16 . 1.370(4) yes
C16 . O9 . 1.183(5) yes
C16 . C17 . 1.484(5) yes
C17 . H171 . 1.000 no
C17 . H172 . 1.000 no
C17 . H173 . 1.000 no
C18 . O10 . 1.450(4) yes
C18 . H181 . 1.000 no
C18 . H182 . 1.000 no
O10 . C19 . 1.285(4) yes
C19 . O11 . 1.168(5) yes
C19 . C20 . 1.473(6) yes
C20 . H201 . 1.000 no
C20 . H202 . 1.000 no
C20 . H203 . 1.000 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . O1 . C5 . 111.65(19) yes
O1 . C1 . C2 . 108.7(2) yes
O1 . C1 . S1 . 108.62(17) yes
C2 . C1 . S1 . 108.97(19) yes
O1 . C1 . H11 . 110.3 no
C2 . C1 . H11 . 110.0 no
S1 . C1 . H11 . 110.1 no
C1 . C2 . C3 . 110.6(2) yes
C1 . C2 . O4 . 107.5(2) yes
C3 . C2 . O4 . 109.71(19) yes
C1 . C2 . H21 . 110.1 no
C3 . C2 . H21 . 107.9 no
O4 . C2 . H21 . 111.0 no
C2 . C3 . C4 . 110.3(2) yes
C2 . C3 . O6 . 108.2(2) yes
C4 . C3 . O6 . 106.8(2) yes
C2 . C3 . H31 . 108.9 no
C4 . C3 . H31 . 110.3 no
O6 . C3 . H31 . 112.3 no
C3 . C4 . C5 . 110.6(2) yes
C3 . C4 . O8 . 109.1(2) yes
C5 . C4 . O8 . 107.4(2) yes
C3 . C4 . H41 . 108.3 no
C5 . C4 . H41 . 110.0 no
O8 . C4 . H41 . 111.5 no
O1 . C5 . C4 . 109.1(2) yes
O1 . C5 . C18 . 106.6(2) yes
C4 . C5 . C18 . 113.8(2) yes
O1 . C5 . H51 . 113.2 no
C4 . C5 . H51 . 105.9 no
C18 . C5 . H51 . 108.5 no
C1 . S1 . S2 . 99.53(11) yes
S1 . S2 . O2 . 107.75(12) yes
S1 . S2 . O3 . 103.69(14) yes
O2 . S2 . O3 . 120.98(17) yes
S1 . S2 . C6 . 106.29(11) yes
O2 . S2 . C6 . 108.63(15) yes
O3 . S2 . C6 . 108.55(16) yes
S2 . C6 . C7 . 118.8(2) yes
S2 . C6 . C11 . 119.0(3) yes
C7 . C6 . C11 . 122.3(3) yes
C6 . C7 . C8 . 119.0(4) yes
C6 . C7 . H71 . 120.5 no
C8 . C7 . H71 . 120.5 no
C7 . C8 . C9 . 120.7(5) yes
C7 . C8 . H81 . 119.7 no
C9 . C8 . H81 . 119.7 no
C8 . C9 . C10 . 120.0(4) yes
C8 . C9 . H91 . 120.0 no
C10 . C9 . H91 . 120.0 no
C9 . C10 . C11 . 121.2(4) yes
C9 . C10 . H101 . 119.4 no
C11 . C10 . H101 . 119.4 no
C6 . C11 . C10 . 116.9(4) yes
C6 . C11 . H111 . 121.6 no
C10 . C11 . H111 . 121.6 no
C2 . O4 . C12 . 117.9(2) yes
O4 . C12 . O5 . 122.5(3) yes
O4 . C12 . C13 . 111.3(3) yes
O5 . C12 . C13 . 126.2(3) yes
C12 . C13 . H131 . 109.5 no
C12 . C13 . H132 . 109.5 no
H131 . C13 . H132 . 109.5 no
C12 . C13 . H133 . 109.5 no
H131 . C13 . H133 . 109.5 no
H132 . C13 . H133 . 109.5 no
C3 . O6 . C14 . 118.93(19) yes
O6 . C14 . O7 . 123.0(3) yes
O6 . C14 . C15 . 111.1(2) yes
O7 . C14 . C15 . 125.9(3) yes
C14 . C15 . H151 . 109.5 no
C14 . C15 . H152 . 109.5 no
H151 . C15 . H152 . 109.5 no
C14 . C15 . H153 . 109.5 no
H151 . C15 . H153 . 109.5 no
H152 . C15 . H153 . 109.5 no
C4 . O8 . C16 . 118.0(2) yes
O8 . C16 . O9 . 122.5(3) yes
O8 . C16 . C17 . 111.7(3) yes
O9 . C16 . C17 . 125.7(3) yes
C16 . C17 . H171 . 109.5 no
C16 . C17 . H172 . 109.5 no
H171 . C17 . H172 . 109.5 no
C16 . C17 . H173 . 109.5 no
H171 . C17 . H173 . 109.5 no
H172 . C17 . H173 . 109.5 no
C5 . C18 . O10 . 106.9(2) yes
C5 . C18 . H181 . 110.1 no
O10 . C18 . H181 . 110.1 no
C5 . C18 . H182 . 110.1 no
O10 . C18 . H182 . 110.1 no
H181 . C18 . H182 . 109.5 no
C18 . O10 . C19 . 118.3(3) yes
O10 . C19 . O11 . 120.2(4) yes
O10 . C19 . C20 . 114.7(4) yes
O11 . C19 . C20 . 125.0(4) yes
C19 . C20 . H201 . 109.5 no
C19 . C20 . H202 . 109.5 no
H201 . C20 . H202 . 109.5 no
C19 . C20 . H203 . 109.5 no
H201 . C20 . H203 . 109.5 no
H202 . C20 . H203 . 109.5 no