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_4036616
_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         'C14 H20 O2'
_chemical_formula_sum            'C14 H20 O2'
_chemical_formula_weight         220.31
_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             15-09-08
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2015-09-08 - Report on C14 H20 O2
            by Anthony C. Willis
            for   Benoit Bolte and Martin Banwell

2015-09-08 - tweak restraints
2015-09-09 - passes checkcif tests with minor 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                   5.8991(1)
_cell_length_b                   12.6249(1)
_cell_length_c                   16.8455(2)
_cell_measurement_reflns_used    10657
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      4
_cell_volume                     1254.58(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.032
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19745
_diffrn_reflns_theta_full        72.340
_diffrn_reflns_theta_max         72.340
_diffrn_reflns_theta_min         4.376
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.599
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.81
_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    1.166
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.297
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.09
_refine_ls_abs_structure_details 'Flack (1983), 1015 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       38(5)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2476
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.0023837
_refine_ls_shift/su_mean         0.0003308
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.19P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0749
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0749
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                2409
_reflns_number_total             2476
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.87
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0296
_oxford_refine_ls_scale          10.2(4)
_oxford_reflns_number_all        2476
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title
'Z:\ban1538BSN\Tony_ban1538BSN_da At 15: 3 on'
_cod_data_source_file            jo6b00043_si_002.cif
_cod_data_source_block           Radudiol_14
_cod_original_sg_symbol_Hall     'P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4036616
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, 
CONT O(1,U'S) O(2,U'S,OCC) UNTIL O(21) 
CONT C(1,U'S) UNTIL C(4) C(5,U'S,OCC) UNTIL C(6) 
CONT C(7,U'S) UNTIL C(14) 
CONT C(51,U'S,OCC) UNTIL C(61) 
CONT ENANTIO EXTPARAM 
EQUIV O(2,OCC) C(5,OCC) UNTIL C(6) O(21,OCC) C(51,OCC) UNTIL C(61) 
WEIGHT -1 O(21,OCC) C(51,OCC) UNTIL C(61) 
RIDE C   (   1,X'S) H   (  11,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) H(42,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) H   (  62,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,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) H   ( 132,X'S) H   ( 133,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) H   ( 143,X'S) 
RIDE C   (   61,X'S) H   (  611,X'S) H   (  612,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
DIST 0.0, .01 = MEAN C(4) TO C(5), C(4) TO C(51) 
DIST 0.0, .01 = MEAN C(5) TO C(6), C(51) TO C(61) 
DIST 0.0, .01 = MEAN C(6) TO C(7), C(61) TO C(7) 
ANGLE 0.0, 1 = MEAN C(4) TO C(5) TO C(6), C(4) TO C(51) TO C(61) 
ANGLE 0.0, 1 = MEAN C(5) TO C(6) TO C(7), C(51) TO C(61) TO C(7) 
ANGLE 0.0, 2 = MEAN C(4) TO C(5) TO O(2), C(6) TO C(5) TO O(2) 
ANGLE 0.0, 2 = MEAN C(4) TO C(51) TO O(21), C(61) TO C(51) TO O(21) 
REM 
U(IJ) 0.0, .01 = O(2) TO O(21) 
U(IJ) 0.0, .01 = C(5) TO C(51) 
U(IJ) 0.0, .01 = C(6) TO C(61) 
REM 
DIST 0.0, .01 = MEAN C(5) TO O(2), C(51) TO O(21) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;