Development of a One-Pot Synthetic Method for Multifunctional Oxazole Derivatives Using Isocyanide Dichloride.
Soeta, Takahiro; Matsumoto, Akihiro; Sakata, Yoko; Ukaji, Yutaka; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b00296

data_4032443
_publ_section_title
;
 Development of a One-Pot Synthetic Method for Multifunctional Oxazole
 Derivatives Using Isocyanide Dichloride.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b00296
_journal_year                    2017
_chemical_formula_moiety         'C23 H20 Br N O3 S2'
_chemical_formula_sum            'C23 H20 Br N O3 S2'
_chemical_formula_weight         502.43
_chemical_name_common            AM-161206
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 93.678(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1665(15)
_cell_length_b                   20.999(2)
_cell_length_c                   6.8761(7)
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      72.855
_cell_measurement_theta_min      3.600
_cell_volume                     2185.4(4)
_computing_cell_refinement       'SAINT V8.37A/APEX3 (Bruker AXS Inc., 2015)'
_computing_data_collection       'Bruker Instrument Service V4.2.9 '
_computing_data_reduction        'SAINT V8.37A/APEX3 (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    ORTEP-3
_computing_publication_material  ORTEP-3
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9926
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.855
_diffrn_reflns_theta_min         3.600
_diffrn_source                   'fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    4.559
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 1996 / Bruker AXS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.960
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.160
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.25(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3102
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0606
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1151P)^2^+0.9571P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1490
_refine_ls_wR_factor_ref         0.1491
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                3093
_reflns_number_total             3102
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00296_si_002.cif
_cod_data_source_block           soeta-AM-161206
_cod_database_code               4032443
_shelx_estimated_absorpt_t_min   0.342
_shelx_estimated_absorpt_t_max   0.804
_shelxl_version_number           2014-3
_shelx_res_checksum              92052
_shelx_hkl_checksum              81055