Diastereo- and Enantioselective Construction of Biologically Important Chiral 1,3-Dioxolochroman Frameworks via Catalytic Asymmetric [4+2] Cycloadditions.
Tu, Man-Su; Liu, Si-Jia; Zhong, Chen; Zhang, Shu; Zhang, Huiwen; Zheng, Yuan-Lin; Shi, Feng; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00119

data_4038241
_publ_section_title
;
 Diastereo- and Enantioselective Construction of Biologically Important
 Chiral 1,3-Dioxolochroman Frameworks via Catalytic Asymmetric [4+2]
 Cycloadditions.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00119
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C33 H26 Cl N O3'
_chemical_formula_sum            'C33 H26 Cl N O3'
_chemical_formula_weight         520.00
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.1430(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7682(2)
_cell_length_b                   8.63480(10)
_cell_length_c                   22.2785(3)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      54.63
_cell_measurement_theta_min      4.228
_cell_volume                     2633.39(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      199.97
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            38114
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.894
_diffrn_reflns_theta_min         4.227
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.018
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1128 before and 0.0627 after correction. The Ratio of minimum to maximum transmission is 0.7870. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.624
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 3586 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     687
_refine_ls_number_reflns         9956
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1089P)^2^+1.0128P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1614
_refine_ls_wR_factor_ref         0.1710
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                8796
_reflns_number_total             9956
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00119_si_002.cif
_cod_data_source_block           190701sf_0m
_cod_database_code               4038241
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.905
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C1A(H1AB), C2A(H2A), C3A(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10A(H10C,H10D)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17), C21(H21),
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C30(H30), C31(H31),
  C32(H32), C33(H33), N1A(H1AA), C5A(H5A), C8A(H8A), C14A(H14A), C15A(H15A),
 C16A(H16A), C17A(H17A), C21A(H21A), C22A(H22A), C23A(H23A), C24A(H24A),
 C25A(H25A), C26A(H26A), C27A(H27A), C30A(H30A), C31A(H31A), C32A(H32A),
 C33A(H33A)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C19A(H19D,H19E,H19F)
;
_shelx_res_checksum              75028
_shelx_hkl_checksum              85216
_olex2_submission_special_instructions 'No special instructions were received'