One-Pot Multicatalytic Approaches for the Synthesis of Cyclohepta[b]indoles, Indolotropones, and Tetrahydrocarbazoles.
Mishra, Uttam K.; Yadav, Sonu; Ramasastry, S. S. V.; The Journal of organic chemistry 82 (2017) 6729–6737; doi:10.1021/acs.joc.7b00865

data_4032678
_publ_section_title
;
 One-Pot Multicatalytic Approaches for the Synthesis of
 Cyclohepta[b]indoles, Indolotropones, and Tetrahydrocarbazoles.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6729
_journal_page_last               6737
_journal_paper_doi               10.1021/acs.joc.7b00865
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C26 H24 Cl N O2 S'
_chemical_formula_sum            'C26 H24 Cl N O2 S'
_chemical_formula_weight         449.97
_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     iterative
_audit_creation_date             2016-12-31
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_cell_angle_alpha                94.950(4)
_cell_angle_beta                 111.217(7)
_cell_angle_gamma                106.268(10)
_cell_formula_units_Z            2
_cell_length_a                   10.333(3)
_cell_length_b                   10.854(3)
_cell_length_c                   11.479(3)
_cell_measurement_reflns_used    2506
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1126.5(5)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
scan:
    Number of images: 472
               Slice: -69.0000 - 119.8000
         Image width: 0.4000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 120.0000
                 XTD: 49.8600
              2theta: 29.8900
scan:
    Number of images: 472
               Slice: -69.0000 - 119.8000
         Image width: 0.4000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 240.0000
                 XTD: 49.8600
              2theta: 29.8900
scan:
    Number of images: 472
               Slice: -69.0000 - 119.8000
         Image width: 0.4000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 0.0000
                 XTD: 49.8600
              2theta: 29.8900
;
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.010974
_diffrn_orient_matrix_UB_12      0.063134
_diffrn_orient_matrix_UB_13      -0.089642
_diffrn_orient_matrix_UB_21      0.028458
_diffrn_orient_matrix_UB_22      -0.055317
_diffrn_orient_matrix_UB_23      -0.075923
_diffrn_orient_matrix_UB_31      -0.077475
_diffrn_orient_matrix_UB_32      0.001368
_diffrn_orient_matrix_UB_33      -0.055945
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9854
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         3.069
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing 1995'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.773
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0706
_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^)+(0.1497P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1964
_refine_ls_wR_factor_ref         0.2174
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2864
_reflns_number_total             3956
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00865_si_003.cif
_cod_data_source_block           gr
_cod_database_code               4032678
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.924
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H4(0.066) H8(0.071) H10(0.079) H11(0.086) H12(0.069) H13(0.096)
 H15(0.087) H17(0.091) H18(0.082) H19(0.088) H20A(0.093) H20B(0.093) H22(0.073)
 H23A(0.154) H23B(0.154) H23C(0.154) H24(0.079) H26(0.101) H27(0.092)
 H29A(0.159) H29B(0.159) H29C(0.159) H30(0.085) H31(0.109)
 Fixed X: H4(-0.0014) H8(-0.2922) H10(0.3458) H11(-0.4148) H12(0.0703) H13(-
 0.0627) H15(-0.2011) H17(-0.0948) H18(0.0015) H19(0.5228) H20A(-0.1557) H20B(-
 0.2914) H22(-0.2091) H23A(-0.4206) H23B(-0.4421) H23C(-0.4192) H24(0.2583)
 H26(-0.3748) H27(0.4317) H29A(0.5637) H29B(0.6361) H29C(0.6909) H30(-0.1419)
 H31(-0.2178)
 Fixed Y: H4(0.1347) H8(0.2313) H10(0.6485) H11(0.1651) H12(0.6676)
 H13(0.1358) H15(0.255) H17(-0.0365) H18(0.8053) H19(0.6932) H20A(-0.0318)
 H20B(0.0149) H22(0.5051) H23A(0.1376) H23B(0.1195) H23C(0.2568) H24(0.2643)
 H26(0.0005) H27(0.3125) H29A(0.561) H29B(0.4641) H29C(0.612) H30(0.7236) H31(-
 0.0996)
 Fixed Z: H4(0.7611) H8(0.783) H10(0.9144) H11(0.9118) H12(0.8853) H13(0.5052)
 H15(0.3997) H17(0.8666) H18(0.7489) H19(0.8315) H20A(0.5974) H20B(0.5771)
 H22(0.4461) H23A(0.4858) H23B(0.3422) H23C(0.4176) H24(0.8009) H26(1.0188)
 H27(0.7144) H29A(0.6233) H29B(0.693) H29C(0.7605) H30(0.5343) H31(0.9946)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'