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_7247902
_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_moiety         'C23 H18 N2'
_chemical_formula_sum            'C23 H18 N2'
_chemical_formula_weight         322.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-31
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-09-19 deposited with the CCDC.	2023-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.92700(10)
_cell_length_b                   11.98670(10)
_cell_length_c                   36.2753(4)
_cell_measurement_reflns_used    11504
_cell_measurement_temperature    99.8(5)
_cell_measurement_theta_max      73.9730
_cell_measurement_theta_min      2.4140
_cell_volume                     3446.83(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.8(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     26.00  77.00   0.50    0.05    --   56.25-125.00 150.00  102
  2  \w     23.00  63.00   0.50    0.05    --   56.25-125.00 -90.00   80
  3  \w    -72.00 -33.00   0.50    0.05    --  -59.44 -15.00-150.00   78
  4  \w    -65.00 -38.00   0.50    0.05    --  -75.32 111.00  60.00   54
  5  \w    -96.00 -42.00   0.50    0.05    --  -75.32 -15.00  90.00  108
  6  \w     38.00  82.00   0.50    0.05    --   75.94 -95.00  30.00   88
  7  \w     39.00  82.00   0.50    0.05    --   83.87-111.00 -60.00   86
  8  \w     37.00  90.00   0.50    0.05    --   75.94-111.00-180.00  106
  9  \w     53.00  82.00   0.50    0.05    --   75.94 -95.00-120.00   58
 10  \w     35.00  70.00   0.50    0.05    --   75.94 -95.00 -60.00   70
 11  \w     53.00  91.00   0.50    0.05    --   83.87 -95.00 -30.00   76
 12  \w     35.00  62.00   0.50    0.05    --   75.94 -95.00   0.00   54
 13  \w     42.00  86.00   0.50    0.05    --   83.87 -95.00  90.00   88
 14  \w     51.00 130.00   0.50    0.05    --   83.87  15.00  60.00  158
 15  \w     92.00 126.00   0.50    0.05    --   75.94  15.00 150.00   68
 16  \w     40.00  85.00   0.50    0.05    --   75.94  15.00 150.00   90
 17  \w     95.00 120.00   0.50    0.05    --   83.87  15.00 -60.00   50
 18  \w     58.00  84.00   0.50    0.05    --   83.87  15.00 -60.00   52
 19  \w     48.00  82.00   0.50    0.05    --   83.87  15.00-120.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0664419000
_diffrn_orient_matrix_UB_12      -0.1140030000
_diffrn_orient_matrix_UB_13      -0.0131546000
_diffrn_orient_matrix_UB_21      -0.1285551000
_diffrn_orient_matrix_UB_22      -0.0008706000
_diffrn_orient_matrix_UB_23      0.0318627000
_diffrn_orient_matrix_UB_31      -0.1296497000
_diffrn_orient_matrix_UB_32      0.0593099000
_diffrn_orient_matrix_UB_33      -0.0248308000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            21562
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.769
_diffrn_reflns_theta_min         2.436
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_coef       0.00080(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         6582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0416P)^2^+0.3139P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0830
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.879
_reflns_number_gt                6048
_reflns_number_total             6582
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc04062c2.cif
_cod_data_source_block           230885lt_auto
_cod_depositor_comments
;
Adding full bibliography for 7247899--7247903.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C46 H36 N4'
_cod_original_formula_weight         644.79
_cod_original_formula_moiety         '2(C23 H18 N2)'
_cod_original_formula_units_Z            4
_cod_database_code               7247902
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.967
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.0(5)
 -0.0(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C19(H19A,H19B), C35(H35A,H35B), C44(H44A,H44B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C28(H28), C29(H29),
  C30(H30), C31(H31), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41),
 C46(H46), C47(H47), C48(H48), C49(H49), C50(H50)
;
_shelx_res_checksum              26290
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.125
_oxdiff_exptl_absorpt_empirical_full_min 0.929