Synthetic Study on Carthamin. 2. Stereoselective Approach to C-Glycosyl Quinochalcone via Desymmetrization.
Hayashi, Taiki; Ohmori, Ken; Suzuki, Keisuke; Organic letters 19 (2017) 866–869; doi:10.1021/acs.orglett.6b03899

data_1545471
_publ_section_title
;
 Synthetic Study on Carthamin. 2. Stereoselective Approach to C-Glycosyl
 Quinochalcone via Desymmetrization.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              866
_journal_page_last               869
_journal_paper_doi               10.1021/acs.orglett.6b03899
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H45 Br1 O18, 0.5(C5 H12)'
_chemical_formula_sum            'C34.5 H51 Br O18'
_chemical_formula_weight         833.66
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.3778(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1264(5)
_cell_length_b                   23.9534(11)
_cell_length_c                   15.5703(7)
_cell_measurement_reflns_used    26654
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      3.39
_cell_volume                     4146.1(3)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2014/07 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2014 (Burla et al., 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID-II IP Area Detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_unetI/netI     0.0856
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            48604
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         68.252
_diffrn_reflns_theta_min         3.388
_diffrn_source                   'rotating anode X-ray tube'
_exptl_absorpt_coefficient_mu    1.969
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1748
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.797
_refine_diff_density_min         -1.005
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details
; 
 Flack x determined using 2480 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.037(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     982
_refine_ls_number_reflns         14920
_refine_ls_number_restraints     123
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.1388
_refine_ls_R_factor_gt           0.0948
_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^)+(0.1807P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2461
_refine_ls_wR_factor_ref         0.2955
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                7682
_reflns_number_total             14920
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03899_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;

2019-02-27
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C32 H45 Br1 O18) (C5 H12)'
_cod_original_formula_sum        'C69 H102 Br2 O36'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     1667.32
_cod_database_code               1545471
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.679
_shelx_estimated_absorpt_t_max   0.883
_shelx_res_checksum              54530
_shelx_hkl_checksum              10040