Ag(I)-catalyzed aminofluorination of alkynes: efficient synthesis of 4-fluoroisoquinolines and 4-fluoropyrrolo[α]isoquinolines.
Xu, Tao; Liu, Guosheng; Organic letters 14 (2012) 5416–5419; doi:10.1021/ol3026507

data_1508742
_publ_section_title
;
 Ag(I)-catalyzed aminofluorination of alkynes: efficient synthesis of
 4-fluoroisoquinolines and 4-fluoropyrrolo[\a]isoquinolines.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5416
_journal_page_last               5419
_journal_paper_doi               10.1021/ol3026507
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C24 H17 F4 N O4'
_chemical_formula_weight         459.39
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.358(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.468(2)
_cell_length_b                   11.7213(13)
_cell_length_c                   16.4807(18)
_cell_measurement_reflns_used    2026
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      43.859
_cell_measurement_theta_min      4.336
_cell_volume                     4129.9(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12291
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60089
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.036
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0583P)^2^+0.6820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1227
_reflns_number_gt                2808
_reflns_number_total             4058
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3026507_si_001.cif
_cod_data_source_block           cd212208
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        4129.9(8)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1508742