Base-promoted Cyclization Reaction of o-Isothiocyanato Arylacetylenes and Aroylacetonitriles: Easy Access to Benzo[d][1,3]thiazines
Shen, Jian; Li, Shumin; Yao, Zhenyu; Lin, Shenghui; Cui, Xiuling; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01424F

data_7158851
_publ_section_title
;
 Base-promoted Cyclization Reaction of o-Isothiocyanato Arylacetylenes and
 Aroylacetonitriles: Easy Access to Benzo[d][1,3]thiazines
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01424F
_journal_year                    2022
_chemical_formula_moiety         'C25 H18 N2 O S'
_chemical_formula_sum            'C25 H18 N2 O S'
_chemical_formula_weight         394.47
_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     iterative
_audit_creation_date             2021-05-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-24 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                75.759(7)
_cell_angle_beta                 74.144(7)
_cell_angle_gamma                73.026(7)
_cell_formula_units_Z            2
_cell_length_a                   9.3178(7)
_cell_length_b                   9.5087(6)
_cell_length_c                   12.5697(10)
_cell_measurement_reflns_used    2268
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7920
_cell_measurement_theta_min      4.9310
_cell_volume                     1007.77(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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   -101.00 -55.00   1.00    1.00    --  -33.50-153.00 -67.00   46
  2  \w   -105.00  38.00   1.00    1.00    --  -33.50   0.00 -60.00  143
  3  \w   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00 -90.00   93
  4  \w     -1.00 109.00   1.00    1.00    --   36.47  19.00 150.00  110
  5  \w     -4.00  77.00   1.00    1.00    --   36.47 -99.00 -90.00   81
  6  \w     57.00 110.00   1.00    1.00    --   36.47 178.00 -30.00   53
  7  \w     18.00 105.00   1.00    1.00    --   36.47  57.00 150.00   87
  8  \w      6.00  63.00   1.00    1.00    --   36.47 -99.00  60.00   57
  9  \w     28.00  75.00   1.00    1.00    --   36.47 -99.00-180.00   47
 10  \w     57.00 109.00   1.00    1.00    --   36.47 178.00  60.00   52
 11  \w     64.00 106.00   1.00    1.00    --   36.47 178.00-120.00   42
 12  \w     61.00  87.00   1.00    1.00    --   36.47 178.00 -60.00   26
 13  \w     69.00 104.00   1.00    1.00    --   36.47  57.00 -90.00   35
 14  \w     85.00 111.00   1.00    2.50    --  108.00-111.00 -30.00   26
 15  \w    139.00 174.00   1.00    2.50    --  108.00 111.00  90.00   35
 16  \w     39.00  68.00   1.00    2.50    --  108.00-111.00 120.00   29
 17  \w     80.00 107.00   1.00    2.50    --  108.00 -94.00 150.00   27
 18  \w    131.00 176.00   1.00    2.50    --  108.00  77.00 120.00   45
 19  \w     64.00 115.00   1.00    2.50    --  108.00 -77.00-150.00   51
 20  \w    125.00 157.00   1.00    2.50    --  108.00  61.00-180.00   32
 21  \w     39.00 121.00   1.00    2.50    --  108.00 -45.00 -30.00   82
 22  \w     37.00 109.00   1.00    2.50    --  108.00 -30.00  60.00   72
 23  \w     82.00 141.00   1.00    2.50    --  108.00  30.00 -30.00   59
 24  \w     85.00 110.00   1.00    2.50    --  108.00-111.00 120.00   25
 25  \w     38.00 128.00   1.00    2.50    --  108.00 -45.00 150.00   90
 26  \w     55.00 128.00   1.00    2.50    --  108.00 -61.00  60.00   73
 27  \w     37.00 178.00   1.00    2.50    --  108.00   0.00 -90.00  141
 28  \w     52.00 107.00   1.00    2.50    --  108.00 -94.00  30.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0940618000
_diffrn_orient_matrix_UB_12      0.0912373000
_diffrn_orient_matrix_UB_13      -0.0885367000
_diffrn_orient_matrix_UB_21      -0.1306616000
_diffrn_orient_matrix_UB_22      0.0645639000
_diffrn_orient_matrix_UB_23      0.0933451000
_diffrn_orient_matrix_UB_31      0.0737780000
_diffrn_orient_matrix_UB_32      0.1310369000
_diffrn_orient_matrix_UB_33      -0.0151172000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7131
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         3.717
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.564
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0746P)^2^+0.0782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1389
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2777
_reflns_number_total             3586
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01424f2.cif
_cod_data_source_block           202105132
_cod_database_code               7158851
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O5N2S1
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.859
_shelx_estimated_absorpt_t_min   0.766
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5), C13(H13), C15(H15), C16(H16),
  C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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 1.190
_oxdiff_exptl_absorpt_empirical_full_min 0.908