A facile one pot synthesis of thiazolo[3,2-a]benzimidazole and pyran fused polyheterocyclic scaffolds.
Mariappan, Arumugam; Rajaguru, Kandasamy; Muthusubramanian, Shanmugam; Bhuvanesh, Nattamai; Organic & biomolecular chemistry 17 (2019) 4196–4199; doi:10.1039/c9ob00300b

data_7156742
_publ_section_title
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 A facile one pot synthesis of thiazolo[3,2-a]benzimidazole and pyran
 fused polyheterocyclic scaffolds.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4196
_journal_page_last               4199
_journal_paper_doi               10.1039/c9ob00300b
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C27 H21 Cl N4 O S, C H4 O'
_chemical_formula_sum            'C28 H25 Cl N4 O2 S'
_chemical_formula_weight         517.03
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-02-04
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_audit_update_record
;
2019-02-05 deposited with the CCDC.    2019-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.472(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.3244(7)
_cell_length_b                   9.7484(3)
_cell_length_c                   23.6714(7)
_cell_measurement_reflns_used    9864
_cell_measurement_temperature    99.99
_cell_measurement_theta_max      70.129
_cell_measurement_theta_min      3.974
_cell_volume                     5134.0(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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_temperature      99.99
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1062
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            81633
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.123
_diffrn_reflns_theta_min         2.332
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.344
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5020
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1316 before and 0.0768 after correction.
The Ratio of minimum to maximum transmission is 0.6664.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       block
_exptl_crystal_F_000             2160
_exptl_crystal_size_max          0.657
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.058
_refine_diff_density_max         1.052
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     655
_refine_ls_number_reflns         9721
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0549
_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^)+(0.0355P)^2^+8.6478P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7595
_reflns_number_total             9721
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00300b2.cif
_cod_data_source_block           bimth
_cod_depositor_comments          'Adding full bibliography for 7156742.cif.'
_cod_database_code               7156742
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.876
_shelx_estimated_absorpt_t_min   0.308
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 N1(H1A,H1B), O1S(H1S)
2.b Rotating group:
 N1B(H1BA,H1BB)
2.c Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C3B(H3B), C4B(H4B)
2.d Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C20B(H20C,H20D)
2.e Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C18(H18), C19(H19),
 C23(H23), C24(H24), C26(H26), C27(H27), C9B(H9B), C10B(H10B), C11B(H11B),
 C12B(H12B), C15B(H15B), C16B(H16B), C18B(H18B), C19B(H19B), C23B(H23B),
 C24B(H24B), C26B(H26B), C27B(H27B)
2.f Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C21B(H21D,H21E,H21F), C2S(H2SA,H2SB,H2SC), C6S(H6SA,H6SB,
 H6SC)
2.g Idealised tetrahedral OH refined as rotating group:
 O5S(H5S)
;
_shelx_res_checksum              51213
_olex2_submission_special_instructions 'No special instructions were received'