Silver-Catalyzed Stereoselective Cyclization to Polysubstituted ( Z)-1,2-Dihydrobenzo[ cd]indoles.
Wang, Qiqi; Zhang, Lianpeng; Yao, Jinzhong; Qiu, Guanyinsheng; Li, Xiaofang; Zhou, Hongwei; The Journal of organic chemistry 83 (2018) 4092–4098; doi:10.1021/acs.joc.7b03257

data_4033542
_publ_section_title
;
 Silver-Catalyzed Stereoselective Cyclization to Polysubstituted (
 Z)-1,2-Dihydrobenzo[ cd]indoles.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4092
_journal_page_last               4098
_journal_paper_doi               10.1021/acs.joc.7b03257
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C26 H21 N O2 S'
_chemical_formula_sum            'C26 H21 N O2 S'
_chemical_formula_weight         411.52
_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
_audit_creation_date             2017-12-20
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                82.019(4)
_cell_angle_beta                 77.797(4)
_cell_angle_gamma                70.070(5)
_cell_formula_units_Z            4
_cell_length_a                   9.9548(5)
_cell_length_b                   11.4972(6)
_cell_length_c                   20.4597(9)
_cell_measurement_reflns_used    5145
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.2030
_cell_measurement_theta_min      4.1020
_cell_volume                     2146.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -24.00  24.00   1.00    1.00    --   36.96 -57.00-150.00   48
  2  \w    -23.00  28.00   1.00    1.00    --   36.96 -57.00 -60.00   51
  3  \w     60.00 104.00   1.00    1.00    --   36.96  57.00-180.00   44
  4  \w    -19.00  31.00   1.00    1.00    --   36.96 -57.00   0.00   50
  5  \w     33.00  72.00   1.00    1.00    --   36.96 -99.00 -90.00   39
  6  \w     -3.00  23.00   1.00    1.00    --   36.96 -99.00 -90.00   26
  7  \w     38.00  63.00   1.00    1.00    --   36.96 -77.00 -60.00   25
  8  \w    -31.00  -5.00   1.00    1.00    --   36.96 -77.00 -60.00   26
  9  \w     -3.00  75.00   1.00    1.00    --   36.96 -99.00 150.00   78
 10  \w     10.00  99.00   1.00    1.00    --   36.96  77.00  60.00   89
 11  \w     41.00 103.00   1.00    1.00    --   36.96  57.00-120.00   62
 12  \w     48.00 125.00   1.00    3.87    --  108.00 -45.00  90.00   77
 13  \w     97.00 129.00   1.00    3.87    --  108.00 -30.00-180.00   32
 14  \w     39.00  74.00   1.00    3.87    --  108.00 -30.00-180.00   35
 15  \w     93.00 168.00   1.00    3.87    --  108.00  61.00 -90.00   75
 16  \w     47.00 109.00   1.00    3.87    --  108.00-111.00-120.00   62
 17  \w    126.00 176.00   1.00    3.87    --  108.00  15.00 150.00   50
 18  \w     62.00 113.00   1.00    3.87    --  108.00-111.00  60.00   51
 19  \w     53.00 124.00   1.00    3.87    --  108.00 -61.00-150.00   71
 20  \w     86.00 112.00   1.00    3.87    --  108.00  15.00 150.00   26
 21  \w     40.00 109.00   1.00    3.87    --  108.00 -95.00 120.00   69
 22  \w     40.00 121.00   1.00    3.87    --  108.00 -45.00 -60.00   81
 23  \w    101.00 167.00   1.00    3.87    --  108.00 111.00-150.00   66
 24  \w    112.00 175.00   1.00    3.87    --  108.00  15.00  30.00   63
 25  \w     71.00 106.00   1.00    3.87    --  108.00 -95.00 -60.00   35
 26  \w     75.00 100.00   1.00    3.87    --  108.00  15.00  30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1193686000
_diffrn_orient_matrix_UB_12      0.0402947000
_diffrn_orient_matrix_UB_13      -0.0489613000
_diffrn_orient_matrix_UB_21      -0.0825737000
_diffrn_orient_matrix_UB_22      0.1362848000
_diffrn_orient_matrix_UB_23      0.0149650000
_diffrn_orient_matrix_UB_31      0.0830617000
_diffrn_orient_matrix_UB_32      -0.0150267000
_diffrn_orient_matrix_UB_33      0.0578379000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14011
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.192
_diffrn_reflns_theta_min         4.434
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_F_000             1140
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         8238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0729P)^2^+0.2291P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1323
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6764
_reflns_number_total             8238
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03257_si_002.cif
_cod_data_source_block           20171013-1
_cod_depositor_comments
;
       Adding full bibliography for 4033542.cif.

2020-06-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        2145.97(19)
_cod_original_formula_moiety     '2(C26 H21 N O2 S)'
_cod_original_formula_sum        'C15 H15 N15 O15 S15'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     1126.32
_cod_database_code               4033542
_chemical_oxdiff_formula         'C H O N S'
_reflns_odcompleteness_completeness 99.87
_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.a Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00J(H00J), C00L(H00L), C00N(H00N), C00O(H00O), C00R(H00R),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C012(H012), C013(H013), C014(H014), C015(H015), C016(H016),
 C017(H017), C018(H018), C019(H019), C01B(H01B), C01C(H01I), C01D(H01D),
 C01E(H01J), C01F(H01K), C01G(H01L), C01H(H01M), C01I(H01N), C01K(H01O)
2.b Idealised Me refined as rotating group:
 C01L(H01A,H01C,H01E), C01M(H01P,H01Q,H01R), C01N(H01S,H01T,H01U), C01O(H01F,
 H01G,H01H)
;
_shelx_res_checksum              59863
_shelx_hkl_checksum              54783
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.383
_oxdiff_exptl_absorpt_empirical_full_min 0.772