Copper-catalyzed synthesis of benzo[4,5]thiazolo[3,2-a]indoles from elemental sulfur and 1-(2-iodophenyl)-1H-indoles
Wang, Zongkang; Yuan, Yang; Jin, Shuxin; Wang, Ye; Gu, Yingge; Wang, Chengyu; Li, Yanzhong; New Journal of Chemistry 47 (2023) 1055–1058; doi:10.1039/D2NJ05660G

data_7062214
_publ_section_title
;
 Copper-catalyzed synthesis of benzo[4,5]thiazolo[3,2-a]indoles from
 elemental sulfur and 1-(2-iodophenyl)-1H-indoles
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1055
_journal_page_last               1058
_journal_paper_doi               10.1039/D2NJ05660G
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C14.051 H10.102 N S0.949'
_chemical_formula_sum            'C14.05 H10.1 N S0.95'
_chemical_formula_weight         223.39
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-23
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_audit_update_record
;
2022-04-10 deposited with the CCDC.	2022-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.775(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6100(7)
_cell_length_b                   8.4073(5)
_cell_length_c                   12.0322(7)
_cell_measurement_reflns_used    9110
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      72.31
_cell_measurement_theta_min      5.00
_cell_volume                     1042.42(11)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_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       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25614
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.456
_diffrn_reflns_theta_min         4.290
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.365
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0908 before and 0.0470 after correction.
The Ratio of minimum to maximum transmission is 0.8169.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       block
_exptl_crystal_F_000             466
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0062(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2049
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.407
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0537P)^2^+0.3912P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.0974
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1977
_reflns_number_total             2049
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj05660g2.cif
_cod_data_source_block           wzk
_cod_depositor_comments          'Adding full bibliography for 7062214.cif.'
_cod_original_formula_sum        'C14.05 H10.10 N S0.95'
_cod_database_code               7062214
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.718
_shelx_estimated_absorpt_t_min   0.518
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C15-C7 \\sim C7-C14 \\sim C15-C4 \\sim C13-C14 \\sim S1-C7 \\sim S2-C7 \\sim
S1-C4 \\sim S2-C13
 with sigma of 0.02
3. Rigid bond restraints
 C14
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
 C15, S1, C14, S2
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C14: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01 within
2A
C15 \\sim S1 \\sim C14 \\sim S2: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01 within 2A
Uanis(C14) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C15) \\sim Ueq, Uanis(S1) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(S2)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
5. Others
 Sof(S2)=1-FVAR(1)
 Sof(C14)=Sof(H14a)=Sof(H14b)=FVAR(1)
 Sof(C15)=Sof(H15a)=Sof(H15b)=1-FVAR(2)
 Sof(S1)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b), C15(H15a,H15b)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C12(H12), C6(H6), C9(H9), C10(H10), C1(H1), C2(H2), C11(H11)
;
_shelx_res_checksum              92518
_olex2_submission_special_instructions 'No special instructions were received'