An Efficient Desulfitative C-C Cross Coupling of Fused Thiazolidine-2-thione with Boronic Acids and Boronic Acid Pinacol esters: Formation of Fused Thiazoles
Rajaguru, Kandasamy; Mariappan, Arumugam; Manjusri, Ramachandran; Muthusubramanian, Shanmugam; Bhuvanesh, Nattamai; RSC Adv.  (2015) –; doi:10.1039/C5RA17827D

data_7222404
_publ_section_title
;
 An Efficient Desulfitative C-C Cross Coupling of Fused
 Thiazolidine-2-thione with Boronic Acids and Boronic Acid Pinacol esters:
 Formation of Fused Thiazoles
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA17827D
_journal_year                    2015
_chemical_formula_moiety         'C15 H9 N S2'
_chemical_formula_sum            'C15 H9 N S2'
_chemical_formula_weight         267.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2015-04-11 deposited with the CCDC.
2015-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.831(3)
_cell_length_b                   11.8166(11)
_cell_length_c                   3.9035(4)
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      37.796
_cell_measurement_theta_min      2.927
_cell_volume                     1191.5(2)
_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  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            55390
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         38.720
_diffrn_reflns_theta_min         1.577
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.424
_exptl_absorpt_correction_T_max  0.7476
_exptl_absorpt_correction_T_min  0.6180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1352 before and 0.0614 after correction.
The Ratio of minimum to maximum transmission is 0.8266.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 2436 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         6578
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0436P)^2^+0.2544P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                6004
_reflns_number_total             6578
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra17827d2.cif
_cod_data_source_block           1
_cod_database_code               7222404
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.813
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15)
;
_shelx_res_checksum              65835
_olex2_submission_special_instructions 'No special instructions were received'