Electrophile promoted cyclization of <i>ortho</i>-aryl substituted ynamides: construction of 3-amino-4-halo- or 4 seleno-isocoumarin derivatives.
Habert, Loïc; Diachenko, Iryna; Retailleau, Pascal; Gillaizeau, Isabelle; Organic & biomolecular chemistry 19 (2021) 6623–6627; doi:10.1039/d1ob01075a

data_7158172
_publ_section_title
;
 Electrophile promoted cyclization of <i>ortho</i>-aryl substituted
 ynamides: construction of 3-amino-4-halo- or 4 seleno-isocoumarin
 derivatives.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6623
_journal_page_last               6627
_journal_paper_doi               10.1039/d1ob01075a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C19 H15 F I N O4 S'
_chemical_formula_sum            'C19 H15 F I N O4 S'
_chemical_formula_weight         499.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2021-05-06 deposited with the CCDC.	2021-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.829(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4116(4)
_cell_length_b                   18.7873(10)
_cell_length_c                   12.5260(6)
_cell_measurement_reflns_used    6642
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0510
_cell_measurement_theta_min      3.9540
_cell_volume                     1956.04(17)
_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_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Dectris HPAD Pilatus3R 200K'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_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  0.0543
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24947
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.056
_diffrn_reflns_theta_min         3.646
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) mm003 X-ray Source'
_exptl_absorpt_coefficient_mu    1.777
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24081
_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_density_diffrn    1.695
_exptl_crystal_description       cube
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.057
_refine_diff_density_min         -0.714
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.0031(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         5262
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0321P)^2^+1.0040P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0910
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3919
_reflns_number_total             5266
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01075a2.cif
_cod_data_source_block           LOH-948
_cod_depositor_comments          'Adding full bibliography for 7158172.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158172
_shelx_res_checksum              63125