Temperature-Controlled Chalcogenation and Chalcogenocyanation of Imidazopyridines in Water under Transition Metal-Free Conditions.
Zhu, Yu-Shen; Xue, Yuting; Liu, Wannian; Zhu, Xinju; Hao, Xin-Qi; Song, Mao-Ping; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01035

data_4038538
_publ_section_title
;
 Temperature-Controlled Chalcogenation and Chalcogenocyanation of
 Imidazopyridines in Water under Transition Metal-Free Conditions.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01035
_journal_year                    2020
_chemical_formula_moiety         'C26 H18 N4 Se'
_chemical_formula_sum            'C26 H18 N4 Se'
_chemical_formula_weight         465.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-04-29
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3346(4)
_cell_length_b                   13.8650(5)
_cell_length_c                   12.6601(4)
_cell_measurement_reflns_used    2627
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5720
_cell_measurement_theta_min      4.5240
_cell_volume                     2113.37(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -94.00  -33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -120.0000 61

  2 omega  -90.00  -63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -120.0000 27

  3 omega   19.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 32

  4 omega   13.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -120.0000 26

  5 omega   58.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -90.0000 35

  6 omega   57.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   30.0000 41

  7 omega   28.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  150.0000 77

  8 omega   62.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 26

  9 omega   64.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 46

 10 omega  -24.00    8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -120.0000 32

 11 omega  -23.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000   90.0000 50

 12 omega   90.00  167.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 77

 13 omega  102.00  176.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 74

 14 omega   52.00   91.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 39

 15 omega   45.00   84.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 39

 16 omega   48.00   97.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 49

 17 omega   55.00   94.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 39

 18 omega   40.00  100.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 60

 19 omega   94.00  166.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 72

 20 omega  103.00  165.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0320556000
_diffrn_orient_matrix_UB_12      -0.0556877000
_diffrn_orient_matrix_UB_13      -0.0940254000
_diffrn_orient_matrix_UB_21      0.0945529000
_diffrn_orient_matrix_UB_22      0.0724237000
_diffrn_orient_matrix_UB_23      -0.0007389000
_diffrn_orient_matrix_UB_31      0.0800025000
_diffrn_orient_matrix_UB_32      -0.0632181000
_diffrn_orient_matrix_UB_33      0.0819098000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8248
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         4.536
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.563
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.463
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0434P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.1009
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2936
_reflns_number_total             3779
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01035_si_002.cif
_cod_data_source_block           201904107
_cod_original_cell_volume        2113.36(11)
_cod_database_code               4038538
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O4
_shelx_estimated_absorpt_t_max   0.766
_shelx_estimated_absorpt_t_min   0.685
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C22(H22), C23(H23), C24(H24),
  C25(H25), C26(H26)
;
_olex2_date_sample_data_collection 1556273592.03
_olex2_submission_special_instructions 'No special instructions were received'