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_7247901
_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_absolute_configuration rm
_chemical_formula_sum            'C21 H12 Br2 N2'
_chemical_formula_weight         452.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 92.968(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.8778(5)
_cell_length_b                   12.9392(17)
_cell_length_c                   16.735(2)
_cell_measurement_reflns_used    3000
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3010
_cell_measurement_theta_min      2.4373
_cell_volume                     838.56(18)
_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  0.0295
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6578
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.303
_diffrn_reflns_theta_min         1.218
_exptl_absorpt_coefficient_mu    4.839
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.7232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            'Pale Yellow'
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lamellar
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Flack x determined using 1322 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.025(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3304
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0255
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0540
_refine_ls_wR_factor_ref         0.0549
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                3059
_reflns_number_total             3304
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc04062c2.cif
_cod_data_source_block           mo_170754LT_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'RM' was changed
to 'rm' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

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_cell_volume        838.57(19)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7247901
_shelxl_version_number           2014/6
_shelx_res_checksum              52492