#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:06:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180374 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/43/7204381.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7204381
loop_
_publ_author_name
'Cai, Yudong'
'Roberts, Brian P.'
'Tocher, Derek A.'
_publ_section_title
;
 Carbohydrate-derived thiols as protic polarity-reversal catalysts for
 enantioselective radical-chain reactions
;
_journal_issue                   11
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              1376
_journal_paper_doi               10.1039/b202022j
_journal_year                    2002
_chemical_formula_sum            'C34 H24 Cl4 O9 S'
_chemical_formula_weight         750.39
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 117.43(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.412(3)
_cell_length_b                   9.096(2)
_cell_length_c                   14.908(3)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      7
_cell_volume                     1734.6(8)
_computing_cell_refinement       NicoletP3
_computing_data_collection       'Nicolet P3'
_computing_data_reduction        XDISK
_computing_molecular_graphics    XP
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       P3
_diffrn_measurement_method       2-theta
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3399
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.72
_diffrn_standards_decay_%        <1%
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.455
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.65
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.015
_refine_ls_goodness_of_fit_obs   1.020
_refine_ls_hydrogen_treatment    fixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         3264
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_restrained_S_obs      1.020
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_obs          0.0490
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0882P)²+0.5645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1410
_refine_ls_wR_factor_obs         0.1232
_reflns_number_observed          2737
_reflns_number_total             3265
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b202022j.txt
_cod_data_source_block           str663
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0882P)^2^+0.5645P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0882P)^2^+0.5645P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1734.6(6)
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7204381
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
S1 S 0.52989(10) 0.1500(2) 0.68791(10) 0.0636(4) Uani 1 d . .
Cl1A Cl 0.6556(5) -0.2395(7) 1.1639(2) 0.240(4) Uani 0.770(6) d P .
Cl1B Cl 0.6838(8) -0.6493(11) 0.9040(7) 0.111(4) Uani 0.230(6) d P .
Cl2 Cl 0.15495(13) -0.9542(2) 0.5597(2) 0.0763(5) Uani 1 d . .
Cl3 Cl 0.22417(15) -0.6517(2) 0.09821(15) 0.0927(6) Uani 1 d . .
Cl4 Cl -0.27269(15) 0.1347(4) 0.0884(3) 0.1605(13) Uani 1 d . .
O1 O 0.4083(2) 0.0854(3) 0.4974(2) 0.0445(7) Uani 1 d . .
O2 O 0.4761(2) -0.1870(4) 0.6997(2) 0.0514(8) Uani 1 d . .
O3 O 0.3972(4) -0.0841(7) 0.7838(3) 0.093(2) Uani 1 d . .
O4 O 0.2941(2) -0.3053(4) 0.5443(3) 0.0478(8) Uani 1 d . .
O5 O 0.3701(4) -0.5040(5) 0.5203(5) 0.096(2) Uani 1 d . .
O6 O 0.2527(2) -0.2233(4) 0.3437(2) 0.0476(8) Uani 1 d . .
O7 O 0.0934(3) -0.1866(6) 0.3321(3) 0.0733(12) Uani 1 d . .
O8 O 0.2188(2) 0.1441(5) 0.3109(2) 0.0538(8) Uani 1 d . .
O9 O 0.1213(3) 0.0147(6) 0.1695(3) 0.0737(12) Uani 1 d . .
C1 C 0.4749(3) 0.0134(5) 0.5895(3) 0.0428(10) Uani 1 d . .
H1A H 0.5302(3) -0.0346(5) 0.5820(3) 0.080 Uiso 1 d R .
C2 C 0.4109(3) -0.1028(5) 0.6114(3) 0.0434(10) Uani 1 d . .
H2A H 0.3569(3) -0.0550(5) 0.6211(3) 0.080 Uiso 1 d R .
C3 C 0.3618(3) -0.2081(6) 0.5231(4) 0.0445(10) Uani 1 d . .
H3A H 0.4150(3) -0.2633(6) 0.5163(4) 0.080 Uiso 1 d R .
C4 C 0.2969(3) -0.1232(6) 0.4277(3) 0.0430(10) Uani 1 d . .
H4A H 0.2420(3) -0.0723(6) 0.4342(3) 0.080 Uiso 1 d R .
C5 C 0.3683(3) -0.0120(5) 0.4122(3) 0.0427(10) Uani 1 d . .
H5A H 0.4256(3) -0.0638(5) 0.4107(3) 0.080 Uiso 1 d R .
C6 C 0.4608(4) -0.1689(8) 0.7820(4) 0.0611(14) Uani 1 d . .
C7 C 0.5276(4) -0.2686(8) 0.8651(4) 0.067(2) Uani 1 d . .
C8 C 0.5613(6) -0.4015(9) 0.8504(6) 0.089(2) Uani 1 d . .
H8A H 0.5427(6) -0.4333(9) 0.7828(6) 0.080 Uiso 1 d R .
C9 C 0.6228(8) -0.4926(14) 0.9287(8) 0.126(4) Uani 1 d . .
C10 C 0.6506(9) -0.4476(18) 1.0236(9) 0.143(5) Uani 1 d . .
H10A H 0.6947(9) -0.5089(18) 1.0795(9) 0.080 Uiso 1 d R .
C11 C 0.6187(8) -0.3126(17) 1.0427(6) 0.130(4) Uani 1 d . .
C12 C 0.5553(6) -0.2196(11) 0.9630(5) 0.095(2) Uani 1 d . .
H12A H 0.5308(6) -0.1272(11) 0.9750(5) 0.080 Uiso 1 d R .
C13 C 0.3070(4) -0.4499(6) 0.5418(4) 0.0500(11) Uani 1 d . .
C14 C 0.2337(4) -0.5345(6) 0.5665(3) 0.0449(10) Uani 1 d . .
C15 C 0.2314(3) -0.6838(6) 0.5562(3) 0.0455(11) Uani 1 d . .
H15A H 0.2763(3) -0.7324(6) 0.5341(3) 0.080 Uiso 1 d R .
C16 C 0.1621(4) -0.7645(6) 0.5774(4) 0.0516(12) Uani 1 d . .
C17 C 0.0958(4) -0.6976(7) 0.6083(4) 0.0558(13) Uani 1 d . .
H17A H 0.0472(4) -0.7545(7) 0.6214(4) 0.080 Uiso 1 d R .
C18 C 0.1000(4) -0.5488(7) 0.6192(5) 0.066(2) Uani 1 d . .
H18A H 0.0549(4) -0.5015(7) 0.6418(5) 0.080 Uiso 1 d R .
C19 C 0.1670(4) -0.4637(7) 0.5979(4) 0.0588(13) Uani 1 d . .
H19A H 0.1683(4) -0.3587(7) 0.6050(4) 0.080 Uiso 1 d R .
C20 C 0.1486(3) -0.2462(6) 0.3024(3) 0.0493(11) Uani 1 d . .
C21 C 0.1113(4) -0.3545(6) 0.2174(3) 0.0500(11) Uani 1 d . .
C22 C 0.1785(4) -0.4408(7) 0.1983(4) 0.0548(12) Uani 1 d . .
H22A H 0.2527(4) -0.4312(7) 0.2390(4) 0.080 Uiso 1 d R .
C23 C 0.1387(4) -0.5403(7) 0.1206(4) 0.0595(13) Uani 1 d . .
C24 C 0.0329(5) -0.5527(7) 0.0596(4) 0.068(2) Uani 1 d . .
H24A H 0.0068(5) -0.6222(7) 0.0051(4) 0.080 Uiso 1 d R .
C25 C -0.0347(4) -0.4653(8) 0.0766(4) 0.072(2) Uani 1 d . .
H25A H -0.1086(4) -0.4744(8) 0.0337(4) 0.080 Uiso 1 d R .
C26 C 0.0028(4) -0.3644(8) 0.1558(4) 0.0622(13) Uani 1 d . .
H26A H -0.0443(4) -0.3024(8) 0.1678(4) 0.080 Uiso 1 d R .
C27 C 0.3131(4) 0.0791(7) 0.3171(4) 0.0543(12) Uani 1 d . .
H27A H 0.3589(4) 0.1556(7) 0.3170(4) 0.080 Uiso 1 d R .
H27B H 0.2959(4) 0.0178(7) 0.2591(4) 0.080 Uiso 1 d R .
C28 C 0.1265(4) 0.1026(6) 0.2316(4) 0.0525(12) Uani 1 d . .
C29 C 0.0364(4) 0.1768(6) 0.2345(3) 0.0529(12) Uani 1 d . .
C30 C -0.0620(4) 0.1312(8) 0.1678(5) 0.0711(15) Uani 1 d . .
H30A H -0.0713(4) 0.0541(8) 0.1205(5) 0.080 Uiso 1 d R .
C31 C -0.1497(5) 0.1955(9) 0.1687(6) 0.084(2) Uani 1 d . .
C32 C -0.1365(5) 0.3056(9) 0.2366(5) 0.078(2) Uani 1 d . .
H32A H -0.1967(5) 0.3485(9) 0.2379(5) 0.080 Uiso 1 d R .
C33 C -0.0383(5) 0.3529(8) 0.3012(5) 0.079(2) Uani 1 d . .
H33A H -0.0300(5) 0.4316(8) 0.3472(5) 0.080 Uiso 1 d R .
C34 C 0.0488(5) 0.2906(8) 0.3018(4) 0.0655(14) Uani 1 d . .
H34A H 0.1176(5) 0.3240(8) 0.3480(4) 0.080 Uiso 1 d R .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C5 112.8(3) . . ?
C6 O2 C2 117.1(4) . . ?
C13 O4 C3 118.6(4) . . ?
C20 O6 C4 116.6(3) . . ?
C28 O8 C27 117.1(4) . . ?
O1 C1 C2 108.6(3) . . ?
O1 C1 S1 108.4(3) . . ?
C2 C1 S1 112.6(3) . . ?
O2 C2 C3 107.9(4) . . ?
O2 C2 C1 111.0(3) . . ?
C3 C2 C1 109.7(3) . . ?
O4 C3 C4 109.3(3) . . ?
O4 C3 C2 106.7(3) . . ?
C4 C3 C2 109.6(4) . . ?
O6 C4 C3 109.3(4) . . ?
O6 C4 C5 110.2(3) . . ?
C3 C4 C5 108.2(3) . . ?
O1 C5 C27 108.4(4) . . ?
O1 C5 C4 107.3(3) . . ?
C27 C5 C4 113.7(4) . . ?
O3 C6 O2 122.7(5) . . ?
O3 C6 C7 125.6(5) . . ?
O2 C6 C7 111.7(5) . . ?
C8 C7 C12 120.1(7) . . ?
C8 C7 C6 123.7(6) . . ?
C12 C7 C6 116.2(7) . . ?
C9 C8 C7 122.7(8) . . ?
C10 C9 C8 118.3(11) . . ?
C10 C9 Cl1B 121.3(9) . . ?
C8 C9 Cl1B 119.3(8) . . ?
C9 C10 C11 121.3(9) . . ?
C10 C11 C12 120.6(9) . . ?
C10 C11 Cl1A 124.9(9) . . ?
C12 C11 Cl1A 114.4(11) . . ?
C7 C12 C11 117.0(10) . . ?
O5 C13 O4 123.1(5) . . ?
O5 C13 C14 124.6(5) . . ?
O4 C13 C14 112.4(4) . . ?
C15 C14 C19 120.5(5) . . ?
C15 C14 C13 118.1(4) . . ?
C19 C14 C13 121.3(5) . . ?
C14 C15 C16 119.0(5) . . ?
C17 C16 C15 121.6(5) . . ?
C17 C16 Cl2 119.1(4) . . ?
C15 C16 Cl2 119.2(4) . . ?
C18 C17 C16 118.6(5) . . ?
C17 C18 C19 121.8(5) . . ?
C18 C19 C14 118.5(5) . . ?
O7 C20 O6 123.2(5) . . ?
O7 C20 C21 124.6(4) . . ?
O6 C20 C21 112.2(4) . . ?
C22 C21 C26 120.5(5) . . ?
C22 C21 C20 122.6(4) . . ?
C26 C21 C20 116.9(5) . . ?
C21 C22 C23 119.5(5) . . ?
C22 C23 C24 121.2(5) . . ?
C22 C23 Cl3 119.2(4) . . ?
C24 C23 Cl3 119.6(4) . . ?
C25 C24 C23 119.9(5) . . ?
C24 C25 C26 120.5(5) . . ?
C25 C26 C21 118.4(6) . . ?
O8 C27 C5 110.9(4) . . ?
O9 C28 O8 122.9(5) . . ?
O9 C28 C29 125.7(5) . . ?
O8 C28 C29 111.5(4) . . ?
C30 C29 C34 119.6(5) . . ?
C30 C29 C28 118.0(5) . . ?
C34 C29 C28 122.4(5) . . ?
C29 C30 C31 120.4(6) . . ?
C32 C31 C30 119.5(6) . . ?
C32 C31 Cl4 120.0(5) . . ?
C30 C31 Cl4 120.5(6) . . ?
C33 C32 C31 119.9(6) . . ?
C32 C33 C34 121.4(7) . . ?
C33 C34 C29 119.2(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.804(5) . ?
Cl1A C11 1.762(12) . ?
Cl1B C9 1.80(2) . ?
Cl2 C16 1.741(6) . ?
Cl3 C23 1.742(6) . ?
Cl4 C31 1.710(7) . ?
O1 C1 1.422(5) . ?
O1 C5 1.433(5) . ?
O2 C6 1.353(6) . ?
O2 C2 1.436(5) . ?
O3 C6 1.208(7) . ?
O4 C13 1.331(7) . ?
O4 C3 1.455(5) . ?
O5 C13 1.200(6) . ?
O6 C20 1.350(5) . ?
O6 C4 1.438(5) . ?
O7 C20 1.202(6) . ?
O8 C28 1.364(6) . ?
O8 C27 1.446(6) . ?
O9 C28 1.199(7) . ?
C1 C2 1.533(6) . ?
C2 C3 1.514(7) . ?
C3 C4 1.506(7) . ?
C4 C5 1.535(6) . ?
C5 C27 1.514(7) . ?
C6 C7 1.477(8) . ?
C7 C8 1.357(11) . ?
C7 C12 1.398(10) . ?
C8 C9 1.372(11) . ?
C9 C10 1.35(2) . ?
C10 C11 1.39(2) . ?
C11 C12 1.401(14) . ?
C13 C14 1.484(7) . ?
C14 C15 1.365(7) . ?
C14 C19 1.405(7) . ?
C15 C16 1.388(7) . ?
C16 C17 1.379(7) . ?
C17 C18 1.361(9) . ?
C18 C19 1.384(8) . ?
C20 C21 1.497(7) . ?
C21 C22 1.374(7) . ?
C21 C26 1.404(7) . ?
C22 C23 1.370(8) . ?
C23 C24 1.373(8) . ?
C24 C25 1.368(9) . ?
C25 C26 1.394(9) . ?
C28 C29 1.482(7) . ?
C29 C30 1.369(8) . ?
C29 C34 1.394(8) . ?
C30 C31 1.398(9) . ?
C31 C32 1.372(11) . ?
C32 C33 1.363(10) . ?
C33 C34 1.374(8) . ?
