Three-component synthesis of 1,4-benzothiazines via iodide-catalyzed aerobic C-H sulfuration with elemental sulfur.
Jiang, Jingjing; Tuo, Xiaolong; Fu, Zhuquan; Huang, Huawen; Deng, Guo-Jun; Organic & biomolecular chemistry 18 (2020) 3234–3238; doi:10.1039/d0ob00074d

data_7157440
_publ_section_title
;
 Three-component synthesis of 1,4-benzothiazines via iodide-catalyzed
 aerobic C-H sulfuration with elemental sulfur.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3234
_journal_page_last               3238
_journal_paper_doi               10.1039/d0ob00074d
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C22 H18 N2 S'
_chemical_formula_sum            'C22 H18 N2 S'
_chemical_formula_weight         342.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-12-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2019-08-08 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.43(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.768(2)
_cell_length_b                   5.0226(10)
_cell_length_c                   17.193(3)
_cell_measurement_reflns_used    2397
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4855
_cell_measurement_theta_min      2.5051
_cell_volume                     839.7(3)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.1186
	          2theta: -20.0407
scan:
	Number of images: 300
	           Slice: -110.0000 - 40.0000
	     Image width: 0.5000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 45.1186
	          2theta: -20.0407
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0787
_diffrn_orient_matrix_UB_12      -0.0618
_diffrn_orient_matrix_UB_13      0.0239
_diffrn_orient_matrix_UB_21      0.0112
_diffrn_orient_matrix_UB_22      -0.0839
_diffrn_orient_matrix_UB_23      -0.1802
_diffrn_orient_matrix_UB_31      0.0331
_diffrn_orient_matrix_UB_32      -0.0428
_diffrn_orient_matrix_UB_33      0.0220
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6116
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.515
_diffrn_reflns_theta_min         3.018
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       rod
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1022 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3658
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0696
_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^)+(0.0301P)^2^+0.7126P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1363
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.921
_reflns_Friedel_fraction_max     0.884
_reflns_number_gt                3175
_reflns_number_total             3658
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00074d2.cif
_cod_data_source_block           sa4493
_cod_depositor_comments          'Adding full bibliography for 7157440.cif.'
_cod_database_code               7157440
_shelxl_version_number           2013-4
_diffrn_number_total             2143
_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:
 C3(H3), C4(H4), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C17(H17), C18(H18), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              96562
_olex2_submission_special_instructions 'No special instructions were received'