Metal-free Sulfonyl Radical-initiated Cascade Cyclization to Access Sulfonated Indolo[1,2-a]quinolines
Sun, Kai; Chen, Xiaolan; Zhang, Yinli; Li, Kai; Huang, Xian-Qiang; Peng, Yu-Yu; Qu, Lingbo; Yu, Bing; Chemical Communications  (2019) –; doi:10.1039/C9CC06924K

data_7124220
_publ_section_title
;
 Metal-free Sulfonyl Radical-initiated Cascade Cyclization to Access
 Sulfonated Indolo[1,2-a]quinolines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC06924K
_journal_year                    2019
_chemical_formula_moiety         'C31 H25 N O2 S'
_chemical_formula_sum            'C31 H25 N O2 S'
_chemical_formula_weight         475.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-10-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-17 deposited with the CCDC.    2019-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.017(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3570(6)
_cell_length_b                   8.1337(4)
_cell_length_c                   14.8816(8)
_cell_measurement_reflns_used    7787
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.547
_cell_measurement_theta_min      2.862
_cell_volume                     1192.16(11)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_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  0.0487
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23659
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.578
_diffrn_reflns_theta_min         2.068
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       plate
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.036
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.192
_refine_ls_abs_structure_details
;
 Flack x determined using 1472 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.19(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5521
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.1416
_refine_ls_R_factor_gt           0.1072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.2000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2598
_refine_ls_wR_factor_ref         0.2842
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3931
_reflns_number_total             5521
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc06924k2.cif
_cod_data_source_block           a_a
_cod_database_code               7124220
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.968
_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. Uiso/Uaniso restraints and constraints
Uanis(C13) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C23)
\\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms
of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C12(H12), C9(H9), C23(H23), C38(H38), C28(H28), C14(H14), C19(H19),
 C24(H24), C27(H27), C37(H37), C1AA(H1AA), C2AA(H2AA), C0AA(H0AA), C5(H5),
 C3AA(H3AA)
3.b Fitted hexagon refined as free rotating group:
 C13(C4,C9,C23,C38,C28)
3.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C34(H34A,H34B,H34C), C4AA(H4AA,H4AB,H4AC)
;
_shelx_res_checksum              62494
_olex2_submission_special_instructions 'No special instructions were received'