Asymmetric construction of six vicinal stereogenic centers on hexahydroxanthones <i>via</i> organocatalytic one-pot reactions.
Zhang, Min; He, Xue-Wen; Xiong, Ya; Zuo, Xiong; Zhou, Wei; Liu, Xiong-Li; Chemical communications (Cambridge, England) 57 (2021) 6764–6767; doi:10.1039/d1cc02570h

data_7128411
_publ_section_title
;
 Asymmetric construction of six vicinal stereogenic centers on
 hexahydroxanthones <i>via</i> organocatalytic one-pot reactions.
;
_journal_issue                   55
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6764
_journal_page_last               6767
_journal_paper_doi               10.1039/d1cc02570h
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         '0.5(C36 H20 Br4 O8)'
_chemical_formula_sum            'C18 H10 Br2 O4'
_chemical_formula_weight         450.08
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-04
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2021-05-16 deposited with the CCDC.	2021-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5529(7)
_cell_length_b                   6.6080(5)
_cell_length_c                   19.3655(12)
_cell_measurement_reflns_used    1689
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      72.0060
_cell_measurement_theta_min      4.1760
_cell_volume                     1606.36(18)
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_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    -86.00 -46.00   1.00    1.00    --  -40.73 125.00 -60.00   40
  2  \w   -113.00 -19.00   1.00    1.00    --  -40.73 -38.00  60.00   94
  3  \w   -113.00 -80.00   1.00    1.00    --  -40.73 -38.00 -30.00   33
  4  \w     35.00  88.00   1.00    1.06    --  107.58 -94.00 -30.00   53
  5  \w     35.00 133.00   1.00    1.06    --  107.58 -45.00   0.00   98
  6  \w     97.00 132.00   1.00    1.06    --  107.58 -30.00  90.00   35
  7  \w     88.00 122.00   1.00    1.06    --  107.58-125.00 120.00   34
  8  \w     34.00  61.00   1.00    1.06    --  107.58 -30.00  90.00   27
  9  \w    115.00 142.00   1.00    1.06    --  107.58 125.00-150.00   27
;
_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      -0.0182566000
_diffrn_orient_matrix_UB_12      0.0546606000
_diffrn_orient_matrix_UB_13      -0.0884494000
_diffrn_orient_matrix_UB_21      -0.0539433000
_diffrn_orient_matrix_UB_22      0.0550355000
_diffrn_orient_matrix_UB_23      0.0839939000
_diffrn_orient_matrix_UB_31      0.2263486000
_diffrn_orient_matrix_UB_32      0.0174468000
_diffrn_orient_matrix_UB_33      0.0128964000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3861
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.537
_diffrn_reflns_theta_min         4.197
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.584
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51563
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.330
_refine_diff_density_min         -1.170
_refine_diff_density_rms         0.242
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0995
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1597P)^2^+12.8020P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2587
_refine_ls_wR_factor_ref         0.2644
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1540
_reflns_number_total             1716
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02570h2.cif
_cod_data_source_block           17-15
_cod_depositor_comments
'Adding full bibliography for 7128410--7128412.cif.'
_cod_database_code               7128411
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.589
_shelx_estimated_absorpt_t_min   0.459
_reflns_odcompleteness_completeness 99.82
_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 O(H) groups
2. Others
 Fixed Sof: H1(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C2(H2), C13(H13), C15(H15), C9(H9), C17(H17), C14(H14), C4(H4)
3.b Tetrahedral OH refined with riding coordinates:
 O1(H1)
;
_shelx_res_checksum              50486
_olex2_date_sample_data_collection 2021-02-04
_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 1.699
_oxdiff_exptl_absorpt_empirical_full_min 0.714