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_1529397
_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_formula_moiety         'C11 H14 Cl I O4'
_chemical_formula_sum            'C11 H14 Cl I O4'
_chemical_formula_weight         372.59
_space_group_IT_number           19
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             14-06-23
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2014-06-20 - Report on C11 H14 Cl I O4
            by Anthony C. Willis
            for  Ehab Taher and Martin Banwell

2014-06-23 - fix H atoms
2014-06-23 - passes checkcif tests

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5023(1)
_cell_length_b                   8.0050(2)
_cell_length_c                   31.0282(8)
_cell_measurement_reflns_used    6337
_cell_measurement_temperature    150
_cell_measurement_theta_max      24
_cell_measurement_theta_min      3
_cell_volume                     1366.67(5)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.21t (release 24-10-2013 CrysAlis171 .NET)
(compiled Oct 24 2013,16:12:21)
;
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2013)'
_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 0.958
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'New Xcalibur, Atlas'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.075
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            29982
_diffrn_reflns_theta_full        27.838
_diffrn_reflns_theta_max         29.782
_diffrn_reflns_theta_min         2.626
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.539
_exptl_absorpt_correction_T_max  0.881
_exptl_absorpt_correction_T_min  0.659
_exptl_absorpt_correction_type   analytical
_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)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.811
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.053
_refine_diff_density_max         1.94
_refine_diff_density_min         -1.95
_refine_ls_abs_structure_details 'Flack (1983), 1411 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3608
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.0014878
_refine_ls_shift/su_mean         0.0000441
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.01P)^2^ + 1.84P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0600
_refine_ls_wR_factor_gt          0.0521
_refine_ls_wR_factor_ref         0.0600
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              43
_reflns_limit_l_min              0
_reflns_number_gt                2925
_reflns_number_total             3608
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.22
_oxford_diffrn_Wilson_scale      0.59
_oxford_refine_ls_r_factor_ref   0.0736
_oxford_refine_ls_scale          1.418(3)
_oxford_reflns_number_all        3608
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Z:\ban1425X\Tony_ban1425X_data\b At 12: 8 on'
_cod_data_source_file            np5b00304_si_002.cif
_cod_data_source_block           ban1425X
_cod_depositor_comments
'Adding full bibliography for 1529395--1529397.cif.'
_cod_original_cell_volume        1366.67(6)
_cod_original_sg_symbol_Hall     'P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               1529397
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
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) 
RIDE C   (   5,X'S) H   (  51,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) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) H   ( 113,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                                                                             
;