Chemoenzymatic Synthesis of the Enantiomer of 4,12-Dihydroxysterpurene, the Structure Assigned to a Metabolite Isolated from the Culture Broth of Stereum purpureum.
Lan, Ping; Banwell, Martin G.; Willis, Anthony C.; Organic letters 17 (2015) 166–169; doi:10.1021/ol5034817

data_1518456
_publ_section_title
;
 Chemoenzymatic Synthesis of the Enantiomer of 4,12-Dihydroxysterpurene,
 the Structure Assigned to a Metabolite Isolated from the Culture Broth of
 Stereum purpureum.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              166
_journal_page_last               169
_journal_paper_doi               10.1021/ol5034817
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_compound_source        local
_chemical_formula_moiety         'C21 H28 O4 S'
_chemical_formula_sum            'C21 H28 O4 S'
_chemical_formula_weight         376.52
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             14-08-27
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2014-08-27 - Report on C21 H28 O4 S
            by Anthony C. Willis
            for  Ping Lan and Martin Banwell

2014-08-27 - passes checkcif tests
;
_cell_angle_alpha                90
_cell_angle_beta                 107.635(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.3925(7)
_cell_length_b                   6.0017(1)
_cell_length_c                   17.9993(6)
_cell_measurement_reflns_used    9777
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      5
_cell_volume                     1996.45(11)
_computing_cell_refinement
;
CrysAlisPro

;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33d (release 23-04-2014 CrysAlis171 .NET)
(compiled Apr 23 2014,17:37:27)
;
_computing_data_reduction
;
CrysAlisPro

;
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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     1.54180
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14696
_diffrn_reflns_theta_full        71.944
_diffrn_reflns_theta_max         71.944
_diffrn_reflns_theta_min         4.698
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.621
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33d (release 23-04-2014 CrysAlis171 .NET)
(compiled Apr 23 2014,17:37:27)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.64
_refine_diff_density_min         -0.46
_refine_ls_abs_structure_details 'Flack (1983), 976 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0367
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3130
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.0020182
_refine_ls_shift/su_mean         0.0001296
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.02P)^2^ +11.21P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1216
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1216
_reflns_limit_h_max              22
_reflns_limit_h_min              -23
_reflns_limit_k_max              7
_reflns_limit_k_min              -5
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                3057
_reflns_number_total             3130
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.03
_oxford_diffrn_Wilson_scale      0.06
_oxford_refine_ls_r_factor_ref   0.0443
_oxford_refine_ls_scale          4.07(6)
_oxford_reflns_number_all        3130
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Z:\ban1439SN\Tony_ban1439SN\ban1 At 12:52 on'
_cod_data_source_file            ol5034817_si_002.cif
_cod_data_source_block           ban1439SN
_cod_depositor_comments
'Adding full bibliography for 1518456--1518457.cif.'
_cod_original_sg_symbol_Hall     'C 2y '
_cod_original_sg_symbol_H-M      'C 1 2 1 '
_cod_database_code               1518456
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, C(1,U'S) UNTIL C(26) 
CONT H(171,X'S) 
CONT ENANTIO 
RIDE C   (   1,X'S) H   (  11,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) H   ( 153,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) H   ( 193,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) H   ( 242,X'S) H   ( 243,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) H   ( 252,X'S) H   ( 253,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) H   ( 262,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                                                                             
;