FeCl3-Promoted Annulation of 2-haloindoles: Switchable Synthesis of Spirooxindole-chromeno[2,3-b]indoles and Spirooxindole-chromeno[3,2-b]indoles.
Luo, Mupeng; Zhu, Xinlei; Liu, Rufeng; Yu, Shunming; Wei, Wanguo; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03300

data_4037955
_publ_section_title
;
 FeCl3-Promoted Annulation of 2-haloindoles: Switchable Synthesis of
 Spirooxindole-chromeno[2,3-b]indoles and
 Spirooxindole-chromeno[3,2-b]indoles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03300
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C24 H17 Br N2 O4 S'
_chemical_formula_sum            'C24 H17 Br N2 O4 S'
_chemical_formula_weight         509.36
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_Hall           'P 4cw'
_space_group_name_H-M_alt        'P 43'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.7367(4)
_cell_length_b                   8.7367(4)
_cell_length_c                   56.083(4)
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.84
_cell_measurement_theta_min      4.40
_cell_volume                     4280.8(4)
_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      170.0
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.950
_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  0.0698
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       63
_diffrn_reflns_limit_l_min       -68
_diffrn_reflns_number            26943
_diffrn_reflns_point_group_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.688
_diffrn_reflns_theta_min         2.742
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.584
_exptl_absorpt_correction_T_max  0.7329
_exptl_absorpt_correction_T_min  0.5561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1449 before and 0.1062 after correction.
The Ratio of minimum to maximum transmission is 0.7588.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_description       block
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         2.363
_refine_diff_density_min         -0.796
_refine_diff_density_rms         0.176
_refine_ls_abs_structure_details
;
 Flack x determined using 2953 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.110(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     581
_refine_ls_number_reflns         7623
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0839
_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^)+(0.1281P)^2^+31.6075P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2309
_refine_ls_wR_factor_ref         0.2347
_reflns_Friedel_coverage         0.901
_reflns_Friedel_fraction_full    0.901
_reflns_Friedel_fraction_max     0.874
_reflns_number_gt                7063
_reflns_number_total             7623
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03300_si_003.cif
_cod_data_source_block           mj19498_0m
_cod_original_cell_volume        4280.8(5)
_cod_database_code               4037955
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.927
_shelx_estimated_absorpt_t_min   0.820
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C13(H13), C14(H14), C19(H19),
 C20(H20), C21(H21), C22(H22), C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A),
 C11A(H11A), C13A(H13A), C14A(H14A), C19A(H19A), C20A(H20A), C21A(H21A),
 C22A(H22A)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C24(H24A,H24B,H24C), C9A(H9AA,H9AB,H9AC), C24A(H24D,H24E,H24F)
;
_shelx_res_checksum              84961
_shelx_hkl_checksum              30259
_olex2_submission_special_instructions 'No special instructions were received'