Diversified Synthesis of Chiral Chromane-Containing Polyheterocyclic Compounds via Asymmetric Organocatalytic Cascade Reactions.
Chen, Ying-Han; Li, De-Hai; Liu, Yan-Kai; ACS omega 3 (2018) 16615–16625; doi:10.1021/acsomega.8b02891

data_4516170
_publ_section_title
;
 Diversified Synthesis of Chiral Chromane-Containing Polyheterocyclic
 Compounds via Asymmetric Organocatalytic Cascade Reactions.
;
_journal_issue                   12
_journal_name_full               'ACS omega'
_journal_page_first              16615
_journal_page_last               16625
_journal_paper_doi               10.1021/acsomega.8b02891
_journal_volume                  3
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C24 H19 N O3 S)'
_chemical_formula_sum            'C48 H38 N2 O6 S2'
_chemical_formula_weight         802.92
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-11-30
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   11.9770(15)
_cell_length_b                   11.9770(15)
_cell_length_c                   47.127(12)
_cell_measurement_reflns_used    7051
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.715
_cell_measurement_theta_min      2.353
_cell_volume                     5854.6(18)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       61
_diffrn_reflns_limit_l_min       -61
_diffrn_reflns_number            34828
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         2.593
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             2520
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 2457 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         8789
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0364P)^2^+0.7767P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.944
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                6527
_reflns_number_total             8789
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b02891_si_001.cif
_cod_data_source_block           lyk_0m
_cod_original_cell_volume        5855(2)
_cod_database_code               4516170
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C5(H5), C6(H6), C25(H25), C29(H29), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C31(H31), C35(H35),
  C36(H36), C37(H37), C38(H38), C40(H40), C41(H41), C42(H42), C43(H43),
 C44(H44), C45(H45), C46(H46), C47(H47), C48(H48)
;
_shelx_res_checksum              94089
_shelx_hkl_checksum              7470
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'