Visible light-mediated copper catalyzed regioselective diamination of terminal alkynes at room temperature: a facile synthesis of substituted imidazo[1,2-α]pyridines
Charpe, Vaibhav Pramod; Gupta, Mahima; Hwang, Kuo Chu; Green Chemistry 26 (2024) 1329–1337; doi:10.1039/D3GC04062C

data_7247899
_publ_section_title
;
 Visible light-mediated copper catalyzed regioselective diamination of
 terminal alkynes at room temperature: a facile synthesis of substituted
 imidazo[1,2-\a]pyridines
;
_journal_issue                   3
_journal_name_full               'Green Chemistry'
_journal_page_first              1329
_journal_page_last               1337
_journal_paper_doi               10.1039/D3GC04062C
_journal_volume                  26
_journal_year                    2024
_chemical_formula_sum            'C21 H12 F2 N2'
_chemical_formula_weight         330.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2023-08-07 deposited with the CCDC.	2023-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.180(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.4478(6)
_cell_length_b                   17.5319(7)
_cell_length_c                   12.9774(4)
_cell_measurement_reflns_used    3181
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.6191
_cell_measurement_theta_min      2.8155
_cell_volume                     3245.0(2)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0305
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12325
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.387
_diffrn_reflns_theta_min         1.841
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.9055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3321
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0605P)^2^+1.2434P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1316
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2370
_reflns_number_total             3321
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc04062c2.cif
_cod_data_source_block           170613LT_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 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7247899--7247903.cif.
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7247899
_shelxl_version_number           2014/6
_shelx_res_checksum              95938