Organocatalytic atroposelective synthesis of naphthoquinone thioglycosides from aryl-naphthoquinones and thiosugars.
Wu, Yuling; Zhou, Wu-Jingyun; Yao, Laiping; Niu, Yadi; Zhao, Hongli; Peng, Cheng; Han, Bo; Huang, Wei; Zhan, Gu; Chemical communications (Cambridge, England) 59 (2023) 7279–7282; doi:10.1039/d3cc01705b

data_7131689
_publ_section_title
;
 Organocatalytic atroposelective synthesis of naphthoquinone
 thioglycosides from aryl-naphthoquinones and thiosugars.
;
_journal_issue                   47
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7279
_journal_page_last               7282
_journal_paper_doi               10.1039/d3cc01705b
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_sum            'C41 H34 O12 S'
_chemical_formula_weight         750.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2023-03-20 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.251(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.2300(4)
_cell_length_b                   7.3747(2)
_cell_length_c                   23.9590(7)
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.86
_cell_measurement_theta_min      3.74
_cell_volume                     1958.43(11)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            30569
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.673
_diffrn_reflns_theta_min         3.738
_exptl_absorpt_coefficient_mu    1.259
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1967 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.058(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     579
_refine_ls_number_reflns         6931
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0630
_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^)+(0.1534P)^2^+0.0106P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1785
_refine_ls_wR_factor_ref         0.1986
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_full    0.930
_reflns_Friedel_fraction_max     0.922
_reflns_number_gt                5494
_reflns_number_total             6931
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01705b5.cif
_cod_data_source_block           20220111_0m_a
_cod_depositor_comments          'Adding full bibliography for 7131689.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7131689
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              69488
_shelx_hkl_checksum              95001