Copper(i)-catalysed oxidative C-N coupling of 2-aminopyridine with terminal alkynes featuring a C[triple bond, length as m-dash]C bond cleavage promoted by visible light.
Ragupathi, Ayyakkannu; Sagadevan, Arunachalam; Lin, Chun-Cheng; Hwu, Jih-Ru; Hwang, Kuo Chu; Chemical communications (Cambridge, England) 52 (2016) 11756–11759; doi:10.1039/c6cc05506k

data_7124919
_publ_section_title
;
 Copper(i)-catalysed oxidative C-N coupling of 2-aminopyridine with
 terminal alkynes featuring a C[triple bond, length as m-dash]C bond
 cleavage promoted by visible light.
;
_journal_issue                   79
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11756
_journal_page_last               11759
_journal_paper_doi               10.1039/c6cc05506k
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C13 H9 F3 N2 O'
_chemical_formula_weight         266.22
_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
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-04-27 deposited with the CCDC.
2016-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                75.267(13)
_cell_angle_beta                 80.383(12)
_cell_angle_gamma                88.880(13)
_cell_formula_units_Z            2
_cell_length_a                   5.6170(11)
_cell_length_b                   7.3899(16)
_cell_length_c                   14.156(3)
_cell_measurement_reflns_used    4050
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.1752
_cell_measurement_theta_min      3.5497
_cell_volume                     560.1(2)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_av_unetI/netI     0.0910
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6889
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.984
_diffrn_reflns_theta_min         1.509
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.9484
_exptl_absorpt_correction_T_min  0.6356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            'white crystal'
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Tabullar
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.832
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.149
_refine_ls_extinction_coef       0.02(2)
_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   1.378
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2216
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.378
_refine_ls_R_factor_all          0.1601
_refine_ls_R_factor_gt           0.1230
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3629
_refine_ls_wR_factor_ref         0.4026
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1277
_reflns_number_total             2216
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc05506k2.cif
_cod_data_source_block           131023lt_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               7124919
_shelxl_version_number           2013-4
_shelx_res_checksum              60251