Stereodivergent, Chemoenzymatic Synthesis of Azaphilone Natural Products.
Pyser, Joshua B.; Baker Dockrey, Summer A.; Benítez, Attabey Rodríguez; Joyce, Leo A.; Wiscons, Ren A.; Smith, Janet L.; Narayan, Alison R. H.; Journal of the American Chemical Society 141 (2019) 18551–18559; doi:10.1021/jacs.9b09385

data_4129083
_publ_section_title
;
 Stereodivergent, Chemoenzymatic Synthesis of Azaphilone Natural Products.
;
_journal_issue                   46
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18551
_journal_page_last               18559
_journal_paper_doi               10.1021/jacs.9b09385
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C17 H14 O5'
_chemical_formula_sum            'C17 H14 O5'
_chemical_formula_weight         298.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-09-24
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.39440(6)
_cell_length_b                   18.0328(2)
_cell_length_c                   29.9372(4)
_cell_measurement_reflns_used    10445
_cell_measurement_temperature    298.43(11)
_cell_measurement_theta_max      76.5860
_cell_measurement_theta_min      3.8300
_cell_volume                     2912.18(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.5a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.5a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.5a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.43(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -72.00 -47.00   0.50    3.00    --  -50.49 117.00 -96.00   50
  2  \w    -76.00 -43.00   0.50   11.80    -- -105.75  19.00  60.00   66
  3  \w    -69.00 -33.00   0.50   11.80    -- -105.75  37.00  90.00   72
  4  \w    -76.00 -32.00   0.50   11.80    -- -105.75  19.00  90.00   88
  5  \w    -76.00 -32.00   0.50   11.80    -- -105.75  19.00 150.00   88
  6  \w    -75.00 -32.00   0.50   11.80    -- -105.75  19.00 -30.00   86
  7  \w    -76.00 -33.00   0.50   11.80    -- -105.75  19.00-120.00   86
  8  \w   -120.00 -70.00   0.50    3.00    --  -50.49-125.00-120.00  100
  9  \w   -120.00 -70.00   0.50   11.80    -- -105.75-161.00  24.00  100
 10  \w   -121.00 -96.00   0.50    3.00    --  -50.49-117.00 175.00   50
 11  \w     60.00  85.00   0.50    3.00    --   50.49 161.00  54.00   50
 12  \w    119.00 145.00   0.50   11.80    --  105.75 117.00 -96.00   52
 13  \w     35.00  69.00   0.50   11.80    --  105.75 -37.00-150.00   68
 14  \w     60.00 119.00   0.50    3.00    --   50.49-161.00  24.00  118
 15  \w     35.00  89.00   0.50   11.80    --  105.75-117.00 175.00  108
 16  \w     33.00  69.00   0.50   11.80    --  105.75 -37.00 120.00   72
 17  \w      5.00  87.00   0.50    3.00    --   50.49-117.00 175.00  164
 18  \w     35.00 141.00   0.50   11.80    --  105.75-161.00  24.00  212
 19  \w   -150.00-125.00   0.50   11.80    -- -105.75-117.00 175.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1127105000
_diffrn_orient_matrix_UB_12      0.0435556000
_diffrn_orient_matrix_UB_13      -0.0393336000
_diffrn_orient_matrix_UB_21      0.1801003000
_diffrn_orient_matrix_UB_22      -0.0388141000
_diffrn_orient_matrix_UB_23      -0.0323810000
_diffrn_orient_matrix_UB_31      -0.1908393000
_diffrn_orient_matrix_UB_32      -0.0623835000
_diffrn_orient_matrix_UB_33      -0.0073197000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            17517
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.601
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         2.861
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.840
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.5a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       plate
_exptl_crystal_F_000             1248
_exptl_crystal_recrystallization_method 'Crystallized from acetonitrile'
_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1850 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         5122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0508P)^2^+0.2019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0846
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4741
_reflns_number_total             5122
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b09385_si_002.cif
_cod_data_source_block           exp_589
_cod_depositor_comments          'Adding full bibliography for 4129083.cif.'
_cod_original_cell_volume        2912.17(6)
_cod_database_code               4129083
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C136 H112 O40 '
_diffrn_oxdiff_ac3_digest_frames
;
010b9ee41e612e20169aa97c5256053c54016805fed
;
_diffrn_oxdiff_ac3_digest_hkl
;
010a49aa1a5f8595ceab7ca0f6bbc26739d869
;
_reflns_odcompleteness_completeness 99.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C29(H29), C33(H33), C15(H15), C25(H25), C8(H8), C10(H10), C27(H27), C12(H12),
 C16(H16), C32(H32)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C6(H6A,H6B,H6C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C),
 C34(H34A,H34B,H34C), C23(H23A,H23B,H23C)
;
_olex2_exptl_crystal_mounting_method 'MiTeGen MicroMount in mineral oil'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.353
_oxdiff_exptl_absorpt_empirical_full_min 0.779