Diastereoselective construction of 4-indole substituted chromans bearing a ketal motif through a three-component Friedel–Crafts alkylation/ketalization sequence
Guo, Jiao-Mei; Wang, Wen-Bo; Guo, Jia; Zhu, Yan-Shuo; Bai, Xu-Guan; Jin, Shao-Jing; Wang, Qi-Lin; Bu, Zhan-Wei; RSC Advances 8 (2018) 15641–; doi:10.1039/C8RA02481B

data_7230562
_publ_section_title
;
 Diastereoselective construction of 4-indole substituted chromans bearing
 a ketal motif through a three-component Friedel--Crafts
 alkylation/ketalization sequence
;
_journal_issue                   28
_journal_name_full               'RSC Advances'
_journal_page_first              15641
_journal_paper_doi               10.1039/C8RA02481B
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C31 H25 Cl2 N O2'
_chemical_formula_sum            'C31 H25 Cl2 N O2'
_chemical_formula_weight         514.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-06-21 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                95.0880(10)
_cell_angle_beta                 91.1550(10)
_cell_angle_gamma                104.0260(10)
_cell_formula_units_Z            2
_cell_length_a                   9.3851(6)
_cell_length_b                   11.5543(8)
_cell_length_c                   12.0921(8)
_cell_measurement_reflns_used    6098
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.69
_cell_measurement_theta_min      2.37
_cell_volume                     1265.96(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19072
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.044
_diffrn_reflns_theta_min         1.692
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.210
_exptl_transmission_factor_max   0.7462
_exptl_transmission_factor_min   0.7000
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         7379
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0559P)^2^+0.2504P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1070
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5878
_reflns_number_total             7379
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra02481b2.cif
_cod_data_source_block           mo_hd_wql2_0m
_cod_database_code               7230562
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.924
_shelx_estimated_absorpt_t_max   0.942
_shelx_res_checksum              46533