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_1529396
_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 syn
_chemical_compound_source        local
_chemical_formula_moiety         'C26 H18 N2 O11'
_chemical_formula_sum            'C26 H18 N2 O11'
_chemical_formula_weight         534.44
_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             15-03-25
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2015-03-25 - Report on C26 H18 N2 O11
            by Anthony C. Willis
            for  Ping Lan and Martin Banwell

2015-03-25 - passes checkcif tests
;
_cell_angle_alpha                90
_cell_angle_beta                 116.016(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.6418(13)
_cell_length_b                   6.1229(2)
_cell_length_c                   21.6668(12)
_cell_measurement_reflns_used    7050
_cell_measurement_temperature    150
_cell_measurement_theta_max      68
_cell_measurement_theta_min      4
_cell_volume                     2580.2(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)
PLATON (Spek, 2008)
;
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_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  0.095
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            48546
_diffrn_reflns_theta_full        69.541
_diffrn_reflns_theta_max         72.290
_diffrn_reflns_theta_min         3.853
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.936
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.87
_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    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.026
_platon_squeeze_details
;
Sluis, P. van der and Spek, A.L. (1990) 
Acta Crystallogr., Sect. A, 46, 194-201.
;
_refine_diff_density_max         0.49
_refine_diff_density_min         -0.43
_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   1.0402
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     703
_refine_ls_number_reflns         5554
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0924
_refine_ls_shift/su_max          0.0066338
_refine_ls_shift/su_mean         0.0011016
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.11P)^2^ + 8.69P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2447
_refine_ls_wR_factor_gt          0.2405
_refine_ls_wR_factor_ref         0.2447
_reflns_limit_h_max              23
_reflns_limit_h_min              -26
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                5122
_reflns_number_total             5556
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.82
_oxford_diffrn_Wilson_scale      0.07
_oxford_refine_ls_r_factor_ref   0.0981
_oxford_refine_ls_scale          4.08(12)
_oxford_reflns_number_all        5554
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title
'Z:\ban1513SN\Tony_ban1513SN_data At 13:58 on'
_cod_data_source_file            np5b00304_si_004.cif
_cod_data_source_block           ban1513SN
_cod_depositor_comments
'Adding full bibliography for 1529395--1529397.cif.'
_cod_original_sg_symbol_Hall     'P 2yb '
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               1529396
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, O(1,U'S) UNTIL O(22) 
CONT N(1,U'S) UNTIL C(52) 
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 ( 7,X'S) H( 71,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 ( 15,X'S) H( 151,X'S) 
RIDE C ( 16,X'S) H( 161,X'S) 
RIDE C ( 18,X'S) H( 181,X'S) 
RIDE C ( 19,X'S) H( 191,X'S) 
RIDE C ( 22,X'S) H( 221,X'S) 
RIDE C ( 23,X'S) H( 231,X'S) 
RIDE C ( 25,X'S) H( 251,X'S) 
RIDE C ( 26,X'S) H( 261,X'S) 
RIDE C ( 28,X'S) H( 281,X'S) 
RIDE C ( 29,X'S) H( 291,X'S) 
RIDE C ( 30,X'S) H( 301,X'S) 
RIDE C ( 31,X'S) H( 311,X'S) 
RIDE C ( 33,X'S) H( 331,X'S) 
RIDE C ( 37,X'S) H( 371,X'S) H( 372,X'S) 
RIDE C ( 38,X'S) H( 381,X'S) H( 382,X'S) H( 383,X'S) 
RIDE C ( 41,X'S) H( 411,X'S) 
RIDE C ( 42,X'S) H( 421,X'S) 
RIDE C ( 44,X'S) H( 441,X'S) 
RIDE C ( 45,X'S) H( 451,X'S) 
RIDE C ( 48,X'S) H( 481,X'S) 
RIDE C ( 49,X'S) H( 491,X'S) 
RIDE C ( 51,X'S) H( 511,X'S) 
RIDE C ( 52,X'S) H( 521,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                                                                             
;