Construction of chiral chroman scaffolds via catalytic asymmetric (4 + 2) cyclizations of para-quinone methide derivatives with 3-vinylindoles.
Wu, Shu-Fang; Tu, Man-Su; Hang, Qing-Qing; Zhang, Shu; Ding, Haixia; Zhang, Yu-Chen; Shi, Feng; Organic & biomolecular chemistry 18 (2020) 5388–5399; doi:10.1039/d0ob01049a

data_7157555
_publ_section_title
;
 Construction of chiral chroman scaffolds via catalytic asymmetric (4 + 2)
 cyclizations of para-quinone methide derivatives with 3-vinylindoles.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5388
_journal_page_last               5399
_journal_paper_doi               10.1039/d0ob01049a
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C38 H40 Br N O2'
_chemical_formula_sum            'C38 H40 Br N O2'
_chemical_formula_weight         622.62
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-23
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-20 deposited with the CCDC.	2020-06-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.382(3)
_cell_length_b                   15.766(4)
_cell_length_c                   20.036(6)
_cell_measurement_reflns_used    4778
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.63
_cell_measurement_theta_min      2.21
_cell_volume                     3279.5(16)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0733
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19417
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         2.777
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.286
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1480 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         7385
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0726P)^2^+0.5432P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1594
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                4683
_reflns_number_total             7385
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01049a2.cif
_cod_data_source_block           sf20190423a_0m
_cod_depositor_comments          'Adding full bibliography for 7157555.cif.'
_cod_original_cell_volume        3279.6(16)
_cod_database_code               7157555
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H36A-H2
 2 with sigma of 0.02
 H37C-H2
 2 with sigma of 0.02
3. Rigid bond restraints
 O1, C1
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2A), C3(H3)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C7(H7), C8(H8), C11(H11), C14(H14), C15(H15), C16(H16),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C30(H30)
4.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,
 H34C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C)
4.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              42048
_olex2_submission_special_instructions 'No special instructions were received'