Construction of Benzo-1,2,3-thiazaphosphole Heterocycles by Annulations of ortho-Phosphinoarenesulfonyl Fluorides with Trimethylsilyl Azide
Luo, Wenjun; Wang, Zhenguo; Cao, Xiaohui; Liang, Dacheng; Wei, Mingjie; Yin, Keshu; Li, Le; The Journal of Organic Chemistry  (2020) –; doi:10.1021/acs.joc.0c01309

data_4038731
_publ_section_title
;
 Construction of Benzo-1,2,3-thiazaphosphole Heterocycles by Annulations
 of ortho-Phosphinoarenesulfonyl Fluorides with Trimethylsilyl Azide
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01309
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H20 N O4 P S'
_chemical_formula_sum            'C21 H20 N O4 P S'
_chemical_formula_weight         413.41
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.493(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6904(2)
_cell_length_b                   14.6998(4)
_cell_length_c                   11.3235(2)
_cell_measurement_reflns_used    12192
_cell_measurement_temperature    230.00(10)
_cell_measurement_theta_max      30.3170
_cell_measurement_theta_min      3.9220
_cell_volume                     1945.24(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      230.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.941
_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    -98.00 -69.00   1.00   15.00    --  -13.71 178.00  90.00   29
  2  \w     45.00  99.00   1.00   15.00    --   14.80 178.00  30.00   54
  3  \w     42.00  80.00   1.00   15.00    --   14.80-178.00 -60.00   38
  4  \w     -1.00  77.00   1.00   15.00    --   14.80  38.00-180.00   78
  5  \w     40.00  98.00   1.00   15.00    --   14.80-178.00 120.00   58
  6  \w    -10.00  25.00   1.00   15.00    --  -13.71 -99.00 120.00   35
  7  \w    -20.00   6.00   1.00   15.00    --   14.80 -38.00 -90.00   26
  8  \w     44.00  71.00   1.00   15.00    --   14.80-178.00-180.00   27
  9  \w     34.00  93.00   1.00   15.00    --   14.80  19.00-120.00   59
 10  \w      8.00  88.00   1.00   15.00    --   14.80  38.00 -60.00   80
 11  \w    -84.00 -59.00   1.00   10.00    --  -13.71 147.00-119.93   25
 12  \w    -72.00 -47.00   1.00   10.00    --  -13.71 128.00 161.74   25
 13  \w    -86.00 -61.00   1.00   10.00    --  -13.71 150.00  13.98   25
 14  \w     22.00  67.00   1.00   10.00    --   14.80  38.00 120.00   45
 15  \w     -6.00  43.00   1.00   10.00    --   14.80 -57.00 120.00   49
 16  \w    -43.00  -9.00   1.00   10.00    --   14.80 -57.00 120.00   34
 17  \w     -8.00  87.00   1.00   10.00    --   14.80  38.00  60.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Mo at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0303304000
_diffrn_orient_matrix_UB_12      0.0138541000
_diffrn_orient_matrix_UB_13      0.0519981000
_diffrn_orient_matrix_UB_21      0.0453481000
_diffrn_orient_matrix_UB_22      -0.0298979000
_diffrn_orient_matrix_UB_23      -0.0138096000
_diffrn_orient_matrix_UB_31      0.0265520000
_diffrn_orient_matrix_UB_32      0.0352645000
_diffrn_orient_matrix_UB_33      -0.0321329000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20033
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.866
_diffrn_reflns_theta_min         3.305
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.412
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 2340 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         5525
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0324
_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^)+(0.0499P)^2^+0.3918P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0865
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.858
_reflns_number_gt                5176
_reflns_number_total             5525
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01309_si_002.cif
_cod_data_source_block           a19101002a0053
_cod_database_code               4038731
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N P S'
_chemical_oxdiff_usercomment     MeOPh-PN
_shelx_estimated_absorpt_t_max   0.922
_shelx_estimated_absorpt_t_min   0.809
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_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:
 C12(H12), C3(H3), C13(H13), C4(H4), C11(H11), C19(H19), C5(H5), C18(H18),
 C6(H6), C17(H17), C10(H10)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C1(H1A,H1B,H1C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              4523
_shelx_hkl_checksum              26638
_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 4.269
_oxdiff_exptl_absorpt_empirical_full_min 0.602