Stereocontrolled construction of six vicinal stereogenic centers on hexahydroxanthone framework through a formal [2+1+3] annulation
Chang, Shun-qin; Zuo, Xiong; Gong, Ying; He, Xue-Wen; Liu, Xiong-Li; Zhou, Ying; Chemical Communications  (2019) –; doi:10.1039/C9CC08101A

data_7124371
_publ_section_title
;
 Stereocontrolled construction of six vicinal stereogenic centers on
 hexahydroxanthone framework through a formal [2+1+3] annulation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC08101A
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H28 N2 O9'
_chemical_formula_sum            'C28 H28 N2 O9'
_chemical_formula_weight         536.52
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-24 deposited with the CCDC.    2019-10-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.46150(10)
_cell_length_b                   10.51450(10)
_cell_length_c                   23.7246(3)
_cell_measurement_reflns_used    11320
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4330
_cell_measurement_theta_min      4.5770
_cell_volume                     2609.65(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_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   -115.00 -17.00   1.00    1.00    --  -40.98 -37.00 -90.00   98
  2  \w   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00  90.00  100
  3  \w     17.00 115.00   1.00    1.00    --   40.98  37.00 -90.00   98
  4  \w     17.00 115.00   1.00    1.00    --   40.98  37.00  90.00   98
  5  \w     31.00 135.00   1.00    1.57    --  106.95 -30.00 -90.00  104
  6  \w     79.00 178.00   1.00    1.57    --  106.95  30.00   0.00   99
  7  \w     34.00 121.00   1.00    1.57    --  106.95-125.00 -60.00   87
  8  \w     31.00 116.00   1.00    1.57    --  106.95-113.00  84.00   85
  9  \w     31.00 140.00   1.00    1.57    --  106.95 -77.00 -90.00  109
 10  \w   -113.00 -65.00   1.00    1.00    --  -40.98-138.00-170.00   48
 11  \w      1.00  82.00   1.00    1.00    --   40.98 -99.00 150.00   81
 12  \w     78.00 162.00   1.00    1.57    --  106.95  61.00 -90.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0146342000
_diffrn_orient_matrix_UB_12      -0.0934302000
_diffrn_orient_matrix_UB_13      0.0495732000
_diffrn_orient_matrix_UB_21      -0.0233456000
_diffrn_orient_matrix_UB_22      0.1095777000
_diffrn_orient_matrix_UB_23      0.0419059000
_diffrn_orient_matrix_UB_31      -0.1446430000
_diffrn_orient_matrix_UB_32      -0.0271334000
_diffrn_orient_matrix_UB_33      -0.0017162000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            15996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.579
_diffrn_reflns_theta_min         3.726
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.861
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 2046 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5148
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0799P)^2^+0.6285P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1239
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                5007
_reflns_number_total             5148
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08101a2.cif
_cod_data_source_block           l_3
_cod_database_code               7124371
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.96
_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 Ternary CH refined with riding coordinates:
 C12(H12), C8(H8), C7(H7), C10(H10), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C4(H4), C17(H17), C19(H19), C20(H20), C18(H18)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C25(H25A,H25B,H25C), C28(H28A,H28B,H28C), C26(H26A,H26B,
 H26C), C22(H22A,H22B,H22C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.641
_oxdiff_exptl_absorpt_empirical_full_min 0.593