CuI nanoparticle-catalyzed synthesis of tetracyclic benzo[e]benzo[4,5]imidazo[1,2-c][1,3]thiazin-6-imine heterocycles by SNAr-type C–S, C–N bond formation from isothiocyanatobenzenes and benzimidazoles
Guo, Xiaolong; Wang, Luyao; Hu, Jing; Zhang, Mengmeng; RSC Advances 8 (2018) 22259–; doi:10.1039/C8RA02552E

data_7230947
_publ_section_title
;
 CuI nanoparticle-catalyzed synthesis of tetracyclic
 benzo[e]benzo[4,5]imidazo[1,2-c][1,3]thiazin-6-imine heterocycles by
 SNAr-type C--S, C--N bond formation from isothiocyanatobenzenes and
 benzimidazoles
;
_journal_issue                   39
_journal_name_full               'RSC Advances'
_journal_page_first              22259
_journal_paper_doi               10.1039/C8RA02552E
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C21 H15 N3 S'
_chemical_formula_sum            'C21 H15 N3 S'
_chemical_formula_weight         341.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2018-01-23 deposited with the CCDC.
2018-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.6530(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.3793(3)
_cell_length_b                   7.23290(10)
_cell_length_c                   19.5343(3)
_cell_measurement_reflns_used    6063
_cell_measurement_temperature    298.87(12)
_cell_measurement_theta_max      73.3960
_cell_measurement_theta_min      6.3480
_cell_volume                     3299.71(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.22a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.22a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.22a (Rigaku OD, 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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.87(12)
_diffrn_detector                 'Image Plate'
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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    -89.00  17.00   0.50    3.00    --    0.00 -37.00-150.00  212
  2  \w    -22.00  89.00   0.50    3.00    --    0.00  57.00  90.00  222
  3  \w    -89.00  18.00   0.50    3.00    --    0.00 -19.00 -60.00  214
  4  \w     24.00 114.00   0.50   14.00    --   94.60 -45.00 150.00  180
  5  \w     75.00 147.00   0.50   14.00    --   94.60  45.00 -90.00  144
  6  \w     19.00 120.00   0.50   14.00    --   94.60 -82.00   0.00  202
  7  \w     13.00 117.00   0.50   14.00    --   94.60 -15.00  90.00  208
  8  \w     36.00  67.50   0.50   14.00    --   94.60 -15.00-150.00   63
  9  \w    111.00 137.00   0.50   14.00    --   94.60  30.00 -60.00   52
 10  \w     12.00 118.00   0.50   14.00    --   94.60 -61.00   0.00  212
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IP'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0260631000
_diffrn_orient_matrix_UB_12      0.0681017000
_diffrn_orient_matrix_UB_13      0.0693749000
_diffrn_orient_matrix_UB_21      0.0597665000
_diffrn_orient_matrix_UB_22      0.0029506000
_diffrn_orient_matrix_UB_23      -0.0299907000
_diffrn_orient_matrix_UB_31      -0.0097406000
_diffrn_orient_matrix_UB_32      0.2018439000
_diffrn_orient_matrix_UB_33      -0.0229106000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8549
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.565
_diffrn_reflns_theta_max         66.565
_diffrn_reflns_theta_min         3.785
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.791
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.22a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.375
_exptl_crystal_description       needle
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2882
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0820P)^2^+1.2330P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1321
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2614
_reflns_number_total             2882
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ra02552e2.cif
_cod_data_source_block           20170912-1
_cod_database_code               7230947
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 98.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_shelx_res_checksum              90616
_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 3.351
_oxdiff_exptl_absorpt_empirical_full_min 0.262