Chemoenzymatic Total Syntheses of the Enantiomers of the Protoilludanes 8-Deoxydihydrotsugicoline and Radudiol.
Chang, Ee Ling; Bolte, Benoit; Lan, Ping; Willis, Anthony C.; Banwell, Martin G.; The Journal of organic chemistry 81 (2016) 2078–2086; doi:10.1021/acs.joc.6b00043

data_4036620
_publ_section_title
;
 Chemoenzymatic Total Syntheses of the Enantiomers of the Protoilludanes
 8-Deoxydihydrotsugicoline and Radudiol.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2078
_journal_page_last               2086
_journal_paper_doi               10.1021/acs.joc.6b00043
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_compound_source        local
_chemical_formula_moiety         'C19 H28 O3 S2'
_chemical_formula_sum            'C19 H28 O3 S2'
_chemical_formula_weight         368.56
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             15-04-10
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2015-04-13 - Report on C12 H22 O4
            by Anthony C. Willis
            for  Ee Ling Chang and Martin Banwell

2015-04-13 - passes checkcif tests with warnings

2015-12-11 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2794(1)
_cell_length_b                   13.2695(1)
_cell_length_c                   23.5284(2)
_cell_measurement_reflns_used    15335
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      4
_cell_volume                     1960.49(4)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2015)'
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
;
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2015)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Supernova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            23376
_diffrn_reflns_theta_full        72.245
_diffrn_reflns_theta_max         72.245
_diffrn_reflns_theta_min         3.757
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.566
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.28
_refine_ls_abs_structure_details 'Flack (1983), 1629 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.005(10)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3887
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0220
_refine_ls_shift/su_max          0.0012515
_refine_ls_shift/su_mean         0.0000928
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.31P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0582
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0582
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              29
_reflns_limit_l_min              0
_reflns_number_gt                3815
_reflns_number_total             3887
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.29
_oxford_diffrn_Wilson_scale      0.07
_oxford_refine_ls_r_factor_ref   0.0226
_oxford_refine_ls_scale          4.02(3)
_oxford_reflns_number_all        3887
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Z:\ban1515SN\Tony_ban1515SN_data At 11:24 on'
_cod_data_source_file            jo6b00043_si_001.cif
_cod_data_source_block           radudiol_7
_cod_original_sg_symbol_Hall     'P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4036620
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   1,X'S) H   (  11,X'S) H   (  12,X'S) H   (  13,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) H   (  22,X'S) H   (  23,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) H   (  42,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) H   ( 123,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) H   ( 163,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) H   ( 173,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) H   ( 193,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;