Chemoenzymatic total synthesis and reassignment of the absolute configuration of ribisin C.
Lan, Ping; Banwell, Martin G.; Ward, Jas S.; Willis, Anthony C.; Organic letters 16 (2014) 228–231; doi:10.1021/ol403220t

data_1513516
_publ_section_title
;
 Chemoenzymatic total synthesis and reassignment of the absolute
 configuration of ribisin C.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              228
_journal_page_last               231
_journal_paper_doi               10.1021/ol403220t
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_compound_source        local
_chemical_formula_moiety         'C14 H14 O5'
_chemical_formula_sum            'C14 H14 O5'
_chemical_formula_weight         262.26
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             13-10-30
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2013-10-30 - Report on C14 H14 O5
            by Anthony C. Willis
            for  Ping Lan and Martin Banwell

2013-10-30 - passes checkcif tests

;
_cell_angle_alpha                90
_cell_angle_beta                 107.933(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.2195(5)
_cell_length_b                   4.7644(3)
_cell_length_c                   13.9604(8)
_cell_measurement_reflns_used    36982
_cell_measurement_temperature    222
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     646.71(6)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_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      222
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.066
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8553
_diffrn_reflns_theta_full        25.046
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_min         2.953
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.11
_refine_diff_density_min         -0.12
_refine_ls_abs_structure_details
;
The enantiomer has been assigned by reference to an unchanging chiral
centre in the synthetic procedure.
;
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1286
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.0013948
_refine_ls_shift/su_mean         0.0003549
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.10P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0967
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0967
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              5
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                1206
_reflns_number_total             1286
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.34
_oxford_diffrn_Wilson_scale      0.11
_oxford_refine_ls_r_factor_ref   0.0407
_oxford_refine_ls_scale          3.33(7)
_oxford_reflns_number_all        1286
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'ban1370 At 11:25 on 30/10'
_cod_data_source_file            ol403220t_si_003.cif
_cod_data_source_block           ban1370
_cod_original_sg_symbol_Hall     'P 2yb '
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               1513516
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  52,X'S) H   (  51,X'S) H   (  53,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) H   (  83,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE O   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
END                                                                             
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_iucr_refine_instruction_details_restraints
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NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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