External Oxidant-Dependent Reactivity Switch in Copper-Mediated Intramolecular Carboamination of Alkynes: Access to a Different Class of Fluorescent Ionic Nitrogen-Doped Polycyclic Aromatic Hydrocarbons.
Shaikh, Aslam C.; Banerjee, Somsuvra; Mule, Ravindra D.; Bera, Saibal; Patil, Nitin T.; The Journal of organic chemistry 84 (2019) 4120–4130; doi:10.1021/acs.joc.9b00120

data_4034214
_publ_section_title
;
 External Oxidant-Dependent Reactivity Switch in Copper-Mediated
 Intramolecular Carboamination of Alkynes: Access to a Different Class of
 Fluorescent Ionic Nitrogen-Doped Polycyclic Aromatic Hydrocarbons.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4120
_journal_page_last               4130
_journal_paper_doi               10.1021/acs.joc.9b00120
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C25 H14 Cl N O, C F3 O3 S'
_chemical_formula_sum            'C26 H14 Cl F3 N O4 S'
_chemical_formula_weight         528.89
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-05-12
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                75.688(7)
_cell_angle_beta                 85.720(7)
_cell_angle_gamma                69.640(8)
_cell_formula_units_Z            2
_cell_length_a                   8.4075(7)
_cell_length_b                   8.9280(8)
_cell_length_c                   16.9361(14)
_cell_measurement_reflns_used    1740
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.5530
_cell_measurement_theta_min      3.3770
_cell_volume                     1154.76(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1640
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.6800
_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      3.00  70.00   1.00   26.04    --   19.75  57.00 -60.00   67
  2  \w     11.00  46.00   1.00   26.04    --  -20.06  77.00  90.00   35
  3  \w    -10.00  90.00   1.00   26.04    --   19.75  77.00   0.00  100
  4  \w     -4.00  32.00   1.00   26.04    --   19.75 -57.00-180.00   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0390108000
_diffrn_orient_matrix_UB_12      -0.0536316000
_diffrn_orient_matrix_UB_13      -0.0259444000
_diffrn_orient_matrix_UB_21      0.0389626000
_diffrn_orient_matrix_UB_22      -0.0634584000
_diffrn_orient_matrix_UB_23      0.0343550000
_diffrn_orient_matrix_UB_31      -0.0711317000
_diffrn_orient_matrix_UB_32      -0.0265353000
_diffrn_orient_matrix_UB_33      0.0039034000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5304
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         2.95
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             538
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.784
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4175
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.784
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1552P)^2^+1.7246P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1901
_refine_ls_wR_factor_ref         0.2187
_reflns_number_gt                3053
_reflns_number_total             4175
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b00120_si_001.cif
_cod_data_source_block           aslambhsi
_cod_original_cell_volume        1154.75(17)
_cod_database_code               4034214
_chemical_oxdiff_formula         'C10 H10 N01 O10 S10 Cl1'
_reflns_odcompleteness_completeness 81.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.365
_oxdiff_exptl_absorpt_empirical_full_min 0.752