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_4034213
_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 H16 N O, C F3 O3 S'
_chemical_formula_sum            'C26 H16 F3 N O4 S'
_chemical_formula_weight         495.46
_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_primary     direct
_audit_creation_date             2017-03-21
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                94.273(5)
_cell_angle_beta                 97.317(5)
_cell_angle_gamma                110.250(5)
_cell_formula_units_Z            2
_cell_length_a                   8.0811(5)
_cell_length_b                   8.9936(5)
_cell_length_c                   16.6202(11)
_cell_measurement_reflns_used    2732
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.7350
_cell_measurement_theta_min      3.7340
_cell_volume                     1114.87(13)
_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
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_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 0.9980
_diffrn_measured_fraction_theta_max 0.8403
_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     20.00  49.00   1.00   13.88    --  -20.06  57.00 -90.00   29
  2  \w     -5.00  90.00   1.00   13.88    --   19.75  77.00   0.00   95
  3  \w    -42.00  51.00   1.00   13.88    --   19.75 -77.00-120.00   93
  4  \w      5.00  58.00   1.00   13.88    --   19.75  57.00 120.00   53
  5  \w    -77.00   4.00   1.00   13.88    --  -20.06 -37.00  90.00   81
  6  \w    -83.00 -52.00   1.00   13.88    --  -20.06 135.00  53.00   31
;
_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      -0.0162982000
_diffrn_orient_matrix_UB_12      0.0169087000
_diffrn_orient_matrix_UB_13      -0.0406354000
_diffrn_orient_matrix_UB_21      -0.0047998000
_diffrn_orient_matrix_UB_22      -0.0774657000
_diffrn_orient_matrix_UB_23      -0.0151738000
_diffrn_orient_matrix_UB_31      -0.0932999000
_diffrn_orient_matrix_UB_32      -0.0299407000
_diffrn_orient_matrix_UB_33      0.0006612000
_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  0.0216
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8185
_diffrn_reflns_theta_full        29.131244
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         2.93
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.929
_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    1.4759
_exptl_crystal_description       niddle
_exptl_crystal_F_000             508.0
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.437091
_refine_diff_density_min         -0.436495
_refine_diff_density_rms         0.079264
_refine_ls_d_res_high            0.729984
_refine_ls_d_res_low             6.956122
_refine_ls_goodness_of_fit_ref   1.304370
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     315
_refine_ls_number_reflns         6011
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.304370
_refine_ls_R_factor_all          0.086422
_refine_ls_R_factor_gt           0.062539
_refine_ls_shift/su_max          0.0403
_refine_ls_shift/su_mean         0.0075
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.220207
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                3650
_reflns_number_total             6011
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b00120_si_002.cif
_cod_data_source_block           ASLAMRB
_cod_database_code               4034213
_chemical_oxdiff_formula         'C10 H10 N10 S10 F10'
_reflns_odcompleteness_completeness 99.80
_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 1.622
_oxdiff_exptl_absorpt_empirical_full_min 0.471