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_7124219
_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         'C30 H23 N O2 S'
_chemical_formula_sum            'C30 H23 N O2 S'
_chemical_formula_weight         461.55
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-06-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-06-21 deposited with the CCDC.    2019-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                67.849(5)
_cell_angle_beta                 83.386(4)
_cell_angle_gamma                89.464(4)
_cell_formula_units_Z            4
_cell_length_a                   11.3349(6)
_cell_length_b                   13.9186(7)
_cell_length_c                   16.1835(8)
_cell_measurement_reflns_used    4956
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9150
_cell_measurement_theta_min      3.5820
_cell_volume                     2347.4(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega -101.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -150.0000 69

  2 omega  -27.00   -1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   19.0000  -90.0000 26

  3 omega   13.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   19.0000  -90.0000 26

  4 omega  -35.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000    0.0000 71

  5 omega   10.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  120.0000 45

  6 omega   19.00   48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  -60.0000 29

  7 omega    5.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  150.0000 46

  8 omega  -28.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000  150.0000 26

  9 omega   32.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 70

 10 omega    7.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -60.0000 64

 11 omega   57.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000  120.0000 47

 12 omega   58.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 50

 13 omega   66.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   90.0000 27

 14 omega   56.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  -60.0000 26

 15 omega   44.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   30.0000 33

 16 omega   67.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -150.0000 35

 17 omega    1.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000   30.0000 25

 18 omega   40.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  150.0000 35

 19 omega   19.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000 -150.0000 54

 20 omega   21.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000  120.0000 80

 21 omega  115.00  160.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 45

 22 omega   88.00  115.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 27

 23 omega   39.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 59

 24 omega   43.00   86.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 43

 25 omega   82.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 27

 26 omega   43.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 48

 27 omega   73.00  101.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 28

 28 omega   37.00  115.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 78

 29 omega   40.00   87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 47

 30 omega   51.00  133.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   30.0000 82

 31 omega   60.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 30

 32 omega   73.00  114.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -150.0000 41

 33 omega   41.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 52

 34 omega   45.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 48

 35 omega   44.00   88.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 44

 36 omega   44.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 65

 37 omega   37.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000   60.0000 140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0959404000
_diffrn_orient_matrix_UB_12      -0.0447681000
_diffrn_orient_matrix_UB_13      -0.0369955000
_diffrn_orient_matrix_UB_21      -0.0066963000
_diffrn_orient_matrix_UB_22      0.1066057000
_diffrn_orient_matrix_UB_23      -0.0764518000
_diffrn_orient_matrix_UB_31      0.0974524000
_diffrn_orient_matrix_UB_32      -0.0305263000
_diffrn_orient_matrix_UB_33      -0.0592105000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17329
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         3.431
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.442
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       prism
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     624
_refine_ls_number_reflns         8385
_refine_ls_number_restraints     52
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0517
_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^)+(0.0806P)^2^+0.0240P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1566
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6064
_reflns_number_total             8385
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc06924k2.cif
_cod_data_source_block           201806285
_cod_database_code               7124219
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N1P2Cu1
_shelx_estimated_absorpt_t_max   0.824
_shelx_estimated_absorpt_t_min   0.761
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 C5A-C4A
 1.39 with sigma of 0.02
 C5-C4
 1.39 with sigma of 0.02
 C6-C5
 1.39 with sigma of 0.02
 C1-C2
 1.39 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C3A) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C2A) \\sim Ueq, Uanis(C2)
\\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C6A) \\sim Ueq, Uanis(C6) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C4) = Uanis(C4A)
Uanis(C3) = Uanis(C3A)
Uanis(C2) = Uanis(C2A)
Uanis(C1) = Uanis(C1A)
Uanis(C5) = Uanis(C5A)
Uanis(C6) = Uanis(C6A)
4. Others
 Sof(C5A)=Sof(C4A)=Sof(H4A)=Sof(C3A)=Sof(H3A)=Sof(C2A)=Sof(H2A)=Sof(C1A)=
 Sof(H1A)=Sof(C6A)=1-FVAR(1)
 Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(C5)=
 Sof(C6)=FVAR(1)
5.a Riding coordinates:
 C13(H13), C4A(H4A)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C16(H16), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26), C28(H28), C29(H29),
  C1'(H1'), C2'(H2'), C3'(H3'), C4'(H4'), C13'(H13'), C14'(H14'), C15'(H15'),
 C16'(H16'), C19'(H19'), C20'(H20'), C21'(H21'), C22'(H22'), C23'(H23'),
 C25'(H25'), C26'(H26'), C28'(H28'), C29'(H29'), C3A(H3A), C2A(H2A), C1A(H1A)
5.c Fitted hexagon refined as free rotating group:
 C5A(C4A,C3A,C2A,C1A,C6A)
5.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C30(H30A,H30B,H30C), C17'(H17D,H17E,H17F), C30'(H30D,
 H30E,H30F)
;
_olex2_submission_special_instructions 'No special instructions were received'