Copper-Promoted Regioselective Intermolecular Diamination of Ynamides: Synthesis of Imidazo[1,2-<i>a</i>]pyridines.
Dwivedi, Vikas; Kumar, Ravi; Sharma, Kavita; Sridhar, Balasubramanian; Reddy, Maddi Sridhar; ACS omega 2 (2017) 2770–2777; doi:10.1021/acsomega.7b00426

data_4516879
_publ_section_title
;
 Copper-Promoted Regioselective Intermolecular Diamination of Ynamides:
 Synthesis of Imidazo[1,2-<i>a</i>]pyridines.
;
_journal_issue                   6
_journal_name_full               'ACS omega'
_journal_page_first              2770
_journal_page_last               2777
_journal_paper_doi               10.1021/acsomega.7b00426
_journal_volume                  2
_journal_year                    2017
_chemical_formula_moiety         '2(C17 H14 F N3 O2), H2 O'
_chemical_formula_sum            'C34 H30 F2 N6 O5'
_chemical_formula_weight         640.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.345(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.975(2)
_cell_length_b                   6.8162(11)
_cell_length_c                   18.711(3)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.71
_cell_volume                     1511.1(4)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  '<i>SHELXL2014</i> (Sheldrick, 2015)'
_computing_structure_solution    '<i>SHELXT</i> (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23789
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.389
_diffrn_reflns_theta_min         2.588
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker,2016'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       block
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3739
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0649
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0376P)^2^+1.6087P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1483
_refine_ls_wR_factor_ref         0.1637
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2632
_reflns_number_total             3739
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            3u_0M_Af.cif
_cod_data_source_block           BS9_0M_A
_cod_original_cell_volume        1511.2(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4516879
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.958
_shelx_estimated_absorpt_t_max   0.977
_shelx_res_checksum              82807
_shelx_hkl_checksum              61926