Direct synthesis of 2-sulfonated 9H-pyrrolo[1,2-a]indoles via NaI-catalyzed cascade radical addition/cyclization/isomerization
Zhang, Pengbo; Gao, Yuzhen; Chen, Su; Tang, Guo; Zhao, Yufen; Organic Chemistry Frontiers 4 (2017) 1350–; doi:10.1039/C7QO00167C

data_1553762
_publ_section_title
;
 Direct synthesis of 2-sulfonated 9H-pyrrolo[1,2-a]indoles via
 NaI-catalyzed cascade radical addition/cyclization/isomerization
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1350
_journal_paper_doi               10.1039/C7QO00167C
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C24 H19 N O2 S'
_chemical_formula_sum            'C24 H19 N O2 S'
_chemical_formula_weight         385.50
_chemical_name_systematic        1-phenyl-2-tosyl-9H-pyrrolo[1,2-a]indole
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_Int_Tables_number      15
_audit_creation_date             2016-01-06
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-09-28 deposited with the CCDC.
2017-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 120.472(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.382(4)
_cell_length_b                   18.322(4)
_cell_length_c                   14.538(3)
_cell_measurement_reflns_used    4351
_cell_measurement_theta_max      25.77
_cell_measurement_theta_min      2.49
_cell_volume                     3760.9(15)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9293
_diffrn_measured_fraction_theta_max 0.9293
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16691
_diffrn_reflns_theta_full        28.8708
_diffrn_reflns_theta_max         28.87
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_min  0.889113
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.0619 before and 0.0346 after correction.
The Ratio of minimum to maximum transmission is 0.8891.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.3616
_exptl_crystal_F_000             1617.6825
_refine_diff_density_max         0.4814
_refine_diff_density_min         -0.3235
_refine_diff_density_rms         0.0698
_refine_ls_d_res_high            0.7360
_refine_ls_d_res_low             11.1837
_refine_ls_goodness_of_fit_ref   1.1214
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4601
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1214
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0546
_refine_ls_shift/su_max          4.5794
_refine_ls_shift/su_mean         0.1934
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1568
_refine_ls_wR_factor_ref         0.1710
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              -21
_reflns_limit_k_max              24
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                3305
_reflns_number_total             4601
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c7qo00167c2.cif
_cod_data_source_block           t0104m
_cod_depositor_comments
;

2025-06-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C4 H3.167 N0.167 O0.333 S0.167'
_cod_original_formula_weight         64.25
_cod_original_formula_moiety         '0.17(C24 H19 N O2 S)'
_cod_original_formula_units_Z            48
_cod_original_cell_volume        3760.7(14)
_cod_database_code               1553762
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'