Copper-Catalyzed Construction of (Z)-Benzo[cd]indoles: Stereoselective Intramolecular trans-Addition and SN-Ar Reaction
Wang, Xinyue; Zeng, Heyang; Zhang, Wenli; Guo, Haiyang; Jin, Tao; Shi, Senlei; Jin, Xiaoyuan; Qu, Na; Liu, Li; Zhang, Lianpeng; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01488B

data_7158898
_publ_section_title
;
 Copper-Catalyzed Construction of (Z)-Benzo[cd]indoles: Stereoselective
 Intramolecular trans-Addition and SN-Ar Reaction
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01488B
_journal_year                    2022
_chemical_formula_moiety         'C25 H18 Cl N O3 S'
_chemical_formula_sum            'C25 H18 Cl N O3 S'
_chemical_formula_weight         447.945
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_audit_creation_date             2022-07-10
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-08-03 deposited with the CCDC.	2022-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.121(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3420(6)
_cell_length_b                   20.8081(13)
_cell_length_c                   10.0336(6)
_cell_measurement_reflns_used    2225
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.9040
_cell_measurement_theta_min      3.0720
_cell_volume                     2156.0(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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.8420
_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    -25.00  22.00   1.00   11.37    --  -15.89 -99.00 150.00   47
  2  \w     36.00  78.00   1.00   11.37    --   16.05 178.00 120.00   42
  3  \w     19.00  71.00   1.00   11.37    --   16.05  19.00  30.00   52
  4  \w      1.00  85.00   1.00   11.37    --   16.05  38.00 -60.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.9990
_diffrn_reflns_Laue_measured_fraction_max 0.8420
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10737
_diffrn_reflns_point_group_measured_fraction_full 0.9990
_diffrn_reflns_point_group_measured_fraction_max 0.8420
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         29.46
_diffrn_reflns_theta_min         2.78
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73050
_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_colour            yellow
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       block
_exptl_crystal_F_000             929.607
_refine_diff_density_max         0.7081
_refine_diff_density_min         -0.7943
_refine_diff_density_rms         0.0787
_refine_ls_d_res_high            0.7226
_refine_ls_d_res_low             7.3293
_refine_ls_goodness_of_fit_ref   1.0375
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5032
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0375
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          -0.0007
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0548P)^2^+1.1294P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1573
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              28
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                3099
_reflns_number_total             5032
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2ob01488b2.cif
_cod_data_source_block           20180329-1
_cod_database_code               7158898
_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:
 C13(H13), C10(H10), C28(H28), C12(H12), C15(H15), C25(H25), C3(H3), C29(H29),
 C19(H19), C26(H26), C16(H16), C18(H18), C4(H4), C5(H5), C11(H11)
2.b Idealised Me refined as rotating group:
 C31(H31a,H31b,H31c)
;
_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
;