Copper-Catalyzed Tandem Radical Cyclization of 8-Ethynyl-1-naphthyl-amines for the Synthesis of 2<i>H</i>-Benzo[<i>e</i>][1,2]thiazine 1,1-Dioxides and its Fluorescence Properties.
Chen, Xia; Zhang, Lianpeng; Wang, Yuzhe; Qiu, Guanyinsheng; Liang, Qinghui; Zhou, Hongwei; The Journal of organic chemistry 85 (2020) 12526–12534; doi:10.1021/acs.joc.0c01725

data_4038762
_publ_section_title
;
 Copper-Catalyzed Tandem Radical Cyclization of
 8-Ethynyl-1-naphthyl-amines for the Synthesis of
 2<i>H</i>-Benzo[<i>e</i>][1,2]thiazine 1,1-Dioxides and its Fluorescence
 Properties.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12526
_journal_page_last               12534
_journal_paper_doi               10.1021/acs.joc.0c01725
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C23 H15 N O2 S2'
_chemical_formula_sum            'C23 H15 N O2 S2'
_chemical_formula_weight         401.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-11
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.617(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7554(19)
_cell_length_b                   7.8485(7)
_cell_length_c                   18.500(3)
_cell_measurement_reflns_used    2650
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9760
_cell_measurement_theta_min      3.9440
_cell_volume                     1869.3(5)
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.856
_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    -19.00  19.00   1.00    1.00    --  -16.05 -99.00  60.00   38
  2  \w     28.00  55.00   1.00    1.00    --   16.36 -99.00-120.00   27
  3  \w    -51.00  30.00   1.00    1.00    --   16.36 -57.00-150.00   81
  4  \w     36.00  84.00   1.00    1.00    --   16.36  57.00   0.00   48
  5  \w     42.00  82.00   1.00    1.00    --   16.36 178.00-150.00   40
;
_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      -0.0009240000
_diffrn_orient_matrix_UB_12      -0.0891630000
_diffrn_orient_matrix_UB_13      0.0060211000
_diffrn_orient_matrix_UB_21      0.0032344000
_diffrn_orient_matrix_UB_22      0.0147023000
_diffrn_orient_matrix_UB_23      0.0386048000
_diffrn_orient_matrix_UB_31      -0.0549939000
_diffrn_orient_matrix_UB_32      0.0022233000
_diffrn_orient_matrix_UB_33      -0.0123206000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9124
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.422
_diffrn_reflns_theta_min         3.040
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93924
_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            yellow
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.050
_refine_diff_density_min         -0.904
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0772
_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^)+(0.1453P)^2^+2.1354P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2327
_refine_ls_wR_factor_ref         0.2639
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3003
_reflns_number_total             4423
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01725_si_003.cif
_cod_data_source_block           20180925-1
_cod_depositor_comments          'Adding full bibliography for 4038762.cif.'
_cod_database_code               4038762
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N S'
_reflns_odcompleteness_completeness 99.68
_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:
 C005(H005), C00A(H00A), C00G(H00G), C00H(H00H), C00I(H00I), C00M(H00M),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S)
2.b Idealised Me refined as rotating group:
 C00L(H00B,H00C,H00D)
;
_shelx_res_checksum              73283
_shelx_hkl_checksum              41180
_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 1.096
_oxdiff_exptl_absorpt_empirical_full_min 0.873