Synthesis of 2-Arylbenzothiazole and 2-Arylthiazole Derivatives via a Ru-Catalyzed <i>meta</i>-Selective C-H Nitration Reaction.
Liu, Deming; Luo, Puying; Ge, Junying; Jiang, Zilin; Peng, Yiyuan; Ding, Qiuping; The Journal of organic chemistry 84 (2019) 12784–12791; doi:10.1021/acs.joc.9b01194

data_4034071
_publ_section_title
;
 Synthesis of 2-Arylbenzothiazole and 2-Arylthiazole Derivatives via a
 Ru-Catalyzed <i>meta</i>-Selective C-H Nitration Reaction.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12784
_journal_page_last               12791
_journal_paper_doi               10.1021/acs.joc.9b01194
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C14 H9 Cl N2 O2 S'
_chemical_formula_sum            'C14 H9 Cl N2 O2 S'
_chemical_formula_weight         304.74
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                102.731(7)
_cell_angle_beta                 90.884(6)
_cell_angle_gamma                112.838(8)
_cell_formula_units_Z            2
_cell_length_a                   7.4014(5)
_cell_length_b                   7.4304(7)
_cell_length_c                   13.2449(9)
_cell_measurement_reflns_used    2624
_cell_measurement_temperature    271.94(10)
_cell_measurement_theta_max      27.6610
_cell_measurement_theta_min      3.7780
_cell_volume                     650.66(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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      N~2~
_diffrn_ambient_temperature      271.94(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.874
_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    -83.00  11.00   1.00   17.58    --  -15.84 -77.00-150.00   94
  2  \w    -83.00   1.00   1.00   17.58    --  -15.84 -57.00  60.00   84
  3  \w    -83.00   1.00   1.00   17.58    --  -15.84 -57.00 150.00   84
  4  \w    -88.00 -35.00   1.00   17.58    --  -15.84-178.00 -60.00   53
  5  \w      0.00  68.00   1.00   17.58    --   16.70  57.00  90.00   68
  6  \w     31.00  56.00   1.00   17.58    --   16.70 -99.00 -30.00   25
  7  \w    -47.00  30.00   1.00   17.58    --   16.70 -57.00 -60.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0586690000
_diffrn_orient_matrix_UB_12      0.0004081000
_diffrn_orient_matrix_UB_13      -0.0418597000
_diffrn_orient_matrix_UB_21      0.0842628000
_diffrn_orient_matrix_UB_22      0.0719382000
_diffrn_orient_matrix_UB_23      0.0339021000
_diffrn_orient_matrix_UB_31      0.0202123000
_diffrn_orient_matrix_UB_32      -0.0790076000
_diffrn_orient_matrix_UB_33      0.0122962000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7196
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.107
_diffrn_reflns_theta_min         3.237
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.455
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0548
_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^)+(0.0420P)^2^+0.5300P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1320
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2346
_reflns_number_total             3049
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01194_si_002.cif
_cod_data_source_block           ldm20170320-1
_cod_database_code               4034071
_shelxl_version_number           2014-1
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.956
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C14(H14), C9(H9), C3(H3), C10(H10), C4(H4)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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 1.366
_oxdiff_exptl_absorpt_empirical_full_min 0.544