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_7128410
_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_absolute_configuration ad
_chemical_formula_moiety         'C21 H21 N O5'
_chemical_formula_sum            'C21 H21 N O5'
_chemical_formula_weight         367.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-13
_audit_creation_method
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-05-08 deposited with the CCDC.	2021-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.023(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.9574(10)
_cell_length_b                   5.9872(3)
_cell_length_c                   14.5153(8)
_cell_measurement_reflns_used    3054
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.2450
_cell_measurement_theta_min      3.5520
_cell_volume                     1907.04(17)
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_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 0.979
_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    -15.00  11.00   1.00    1.00    --  -40.98 107.00  26.00   26
  2  \w    -79.00 -35.00   1.00    1.00    --  -40.98 107.00  26.00   44
  3  \w   -111.00 -27.00   1.00    1.00    --  -40.98 -38.00-120.00   84
  4  \w   -113.00 -17.00   1.00    1.00    --  -40.98 -57.00 150.00   96
  5  \w     33.00 102.00   1.00    2.00    --  106.95 -95.00 -90.00   69
  6  \w     33.00  89.00   1.00    1.60    --  106.95 -95.00-150.00   56
  7  \w     74.00 178.00   1.00    1.60    --  106.95  15.00 -60.00  104
  8  \w    111.00 178.00   1.00    1.60    --  106.95 125.00  90.00   67
  9  \w     89.00 177.00   1.00    1.60    --  106.95  45.00-180.00   88
 10  \w     52.00  88.00   1.00    1.60    --  106.95 -95.00  90.00   36
 11  \w    -89.00 -28.00   1.00    1.60    --  -42.52 -77.00   0.00   61
 12  \w     69.00 107.00   1.00    1.60    --   42.68 178.00-180.00   38
 13  \w     81.00 121.00   1.00    1.60    --   42.68 178.00 -30.00   40
 14  \w   -116.00 -91.00   1.00    1.26    --  -41.23 -77.00 -60.00   25
 15  \w    -49.00 -23.00   1.00    1.26    --  -41.23 -77.00 -60.00   26
 16  \w     20.00  46.00   1.00    1.26    --   41.23  57.00   0.00   26
 17  \w     30.00  56.00   1.00    1.26    --   41.23  38.00 -30.00   26
 18  \w      6.00  48.00   1.00    1.26    --   41.23 -99.00-150.00   42
 19  \w     15.00  40.00   1.00    1.26    --   41.23  57.00  30.00   25
 20  \w     79.00 105.00   1.00    1.67    --  106.95  61.00 -30.00   26
 21  \w    149.00 175.00   1.00    1.67    --  106.95  77.00 -90.00   26
 22  \w     83.00 124.00   1.00    1.67    --  106.95  45.00  30.00   41
 23  \w     74.00 100.00   1.00    1.67    --  106.95  77.00 -60.00   26
 24  \w     78.00 103.00   1.00    1.67    --  106.95  61.00  30.00   25
 25  \w     80.00 106.00   1.00    1.67    --  106.95  61.00-120.00   26
;
_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      -0.0568181000
_diffrn_orient_matrix_UB_12      -0.0504642000
_diffrn_orient_matrix_UB_13      0.0556543000
_diffrn_orient_matrix_UB_21      -0.0408738000
_diffrn_orient_matrix_UB_22      0.0369300000
_diffrn_orient_matrix_UB_23      -0.0871767000
_diffrn_orient_matrix_UB_31      0.0054418000
_diffrn_orient_matrix_UB_32      -0.2495692000
_diffrn_orient_matrix_UB_33      -0.0241643000
_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  0.0181
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6212
_diffrn_reflns_point_group_measured_fraction_full 0.875
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.445
_diffrn_reflns_theta_min         3.593
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52559
_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    1.280
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 870 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(15)
_refine_ls_extinction_coef       0.0023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3225
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0636
_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^)+(0.0908P)^2^+0.9578P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1766
_refine_ls_wR_factor_ref         0.1874
_reflns_Friedel_coverage         0.556
_reflns_Friedel_fraction_full    0.721
_reflns_Friedel_fraction_max     0.666
_reflns_number_gt                2747
_reflns_number_total             3225
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02570h2.cif
_cod_data_source_block           cxy-d-15
_cod_depositor_comments
'Adding full bibliography for 7128410--7128412.cif.'
_cod_original_cell_volume        1907.05(16)
_cod_database_code               7128410
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 100.00
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C13(H13), C9(H9), C11(H11), C8(H8), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C19(H19), C15(H15), C16(H16), C18(H18), C17(H17), C1(H1), C2(H2)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              66472
_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 2.000
_oxdiff_exptl_absorpt_empirical_full_min 0.515