Chemoenzymatic Synthesis of (+)-Asperpentyn and the Enantiomer of the Structure Assigned to Aspergillusol A.
Lan, Ping; White, Lauren E.; Taher, Ehab S.; Guest, Prudence E.; Banwell, Martin G.; Willis, Anthony C.; Journal of natural products 78 (2015) 1963–1968; doi:10.1021/acs.jnatprod.5b00304

data_1529395
_publ_section_title
;
 Chemoenzymatic Synthesis of (+)-Asperpentyn and the Enantiomer of the
 Structure Assigned to Aspergillusol A.
;
_journal_issue                   8
_journal_name_full               'Journal of natural products'
_journal_page_first              1963
_journal_page_last               1968
_journal_paper_doi               10.1021/acs.jnatprod.5b00304
_journal_volume                  78
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_compound_source        local
_chemical_formula_moiety         'C9 H13 I O4'
_chemical_formula_sum            'C9 H13 I O4'
_chemical_formula_weight         312.10
_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   geom
_atom_sites_solution_primary     heavy
_audit_creation_date             13-11-20
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2013-11-21 - Report on C9 H13 I O4
            by Anthony C. Willis
            for  Ehab Taher and Martin Banwell

2013-11-21 - passes checkcif tests

;
_cell_angle_alpha                90
_cell_angle_beta                 92.9213(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.7416(4)
_cell_length_b                   5.1188(1)
_cell_length_c                   12.1148(3)
_cell_measurement_reflns_used    13178
_cell_measurement_temperature    200
_cell_measurement_theta_max      30
_cell_measurement_theta_min      3
_cell_volume                     1098.78(4)
_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    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.059
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16018
_diffrn_reflns_theta_full        30.027
_diffrn_reflns_theta_max         30.027
_diffrn_reflns_theta_min         2.918
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.902
_exptl_absorpt_correction_T_max  0.866
_exptl_absorpt_correction_T_min  0.457
_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    1.887
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.62
_refine_diff_density_min         -0.99
_refine_ls_abs_structure_details 'Flack (1983), 1325 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         3090
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0237
_refine_ls_shift/su_max          0.0003951
_refine_ls_shift/su_mean         0.0000763
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 2.11P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0578
_refine_ls_wR_factor_gt          0.0566
_refine_ls_wR_factor_ref         0.0578
_reflns_limit_h_max              24
_reflns_limit_h_min              -24
_reflns_limit_k_max              7
_reflns_limit_k_min              -6
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                2918
_reflns_number_total             3091
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.27
_oxford_diffrn_Wilson_scale      10.16
_oxford_refine_ls_r_factor_ref   0.0259
_oxford_refine_ls_scale          0.3618(3)
_oxford_reflns_number_all        3090
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'ban1371 At 14:51 on 1/11'
_cod_data_source_file            np5b00304_si_003.cif
_cod_data_source_block           ban1371
_cod_depositor_comments
'Adding full bibliography for 1529395--1529397.cif.'
_cod_original_sg_symbol_Hall     'C 2y '
_cod_original_sg_symbol_H-M      'C 1 2 1 '
_cod_database_code               1529395
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE O   (   3,X'S) H   (   3,X'S) 
RIDE O   (   4,X'S) H   (   4,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) 
RIDE C   (   5,X'S) H   (  51,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) H   (  92,X'S) H   (  93,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                                                                             
;