Sequential Regioselective Di-organochalcogenations of Imidazo[1,2-<i>a</i>]pyrimidines using I<sub>2</sub>/H<sub>3</sub>PO<sub>4</sub> in DMSO.
Obah Kosso, Anne Roly; Kabri, Youssef; Broggi, Julie; Redon, Sébastien; Vanelle, Patrice; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b02963

data_4037890
_publ_section_title
;
 Sequential Regioselective Di-organochalcogenations of
 Imidazo[1,2-<i>a</i>]pyrimidines using
 I<sub>2</sub>/H<sub>3</sub>PO<sub>4</sub> in DMSO.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02963
_journal_year                    2020
_chemical_formula_moiety         'C27 H23 N3 O3 S Se'
_chemical_formula_sum            'C27 H23 N3 O3 S Se'
_chemical_formula_weight         548.50
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-11-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                72.6850(10)
_cell_angle_beta                 72.1330(10)
_cell_angle_gamma                85.1920(10)
_cell_formula_units_Z            2
_cell_length_a                   9.50100(10)
_cell_length_b                   10.47140(10)
_cell_length_c                   13.6454(3)
_cell_measurement_reflns_used    24221
_cell_measurement_temperature    298
_cell_measurement_theta_max      70.7980
_cell_measurement_theta_min      4.4020
_cell_volume                     1233.49(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_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      0.00  29.00   1.00    1.00    --   38.00  91.00 -10.44   29
  2  \w   -113.00 -13.00   1.00    1.00    --  -41.07 -57.00 -30.00  100
  3  \w    -69.00  32.00   1.00    1.00    --  -41.07  57.00 150.00  101
  4  \w   -115.00 -17.00   1.00    1.00    --  -41.07 -38.00-180.00   98
  5  \w   -115.00 -17.00   1.00    1.00    --  -41.07 -38.00  60.00   98
  6  \w      8.00 117.00   1.00    1.00    --   41.07  77.00 150.00  109
  7  \w     23.00  97.00   1.00    1.00    --   41.07-125.00   0.00   74
  8  \w     11.00  38.00   1.00    1.00    --   46.00  84.00 -22.95   27
  9  \w     11.00  38.00   1.00    1.00    --   46.00  84.00  43.01   27
 10  \w     12.00  45.00   1.00    1.00    --   46.00  81.00-142.57   33
 11  \w     16.00  45.00   1.00    1.00    --   50.00  82.00-110.06   29
 12  \w     16.00  45.00   1.00    1.00    --   50.00  81.00 139.98   29
 13  \w     30.00 137.00   1.00    1.00    --   62.00  75.00  66.15  107
 14  \w     30.00 137.00   1.00    1.00    --   62.00  75.00 -31.41  107
 15  \w     34.00 142.00   1.00    1.00    --   66.00  76.00  96.63  108
 16  \w     34.00 142.00   1.00    1.00    --   66.00  76.00 -76.09  108
 17  \w     37.00 146.00   1.00    1.00    --   70.00  77.00-166.47  109
 18  \w     38.00 146.00   1.00    1.00    --   70.00  76.00 131.25  108
 19  \w     37.00 146.00   1.00    1.00    --   70.00  77.00  16.01  109
 20  \w     37.00 146.00   1.00    1.00    --   70.00  77.00-120.73  109
 21  \w     41.00 150.00   1.00    4.00    --   74.00  77.00 -27.74  109
 22  \w     42.00 150.00   1.00    4.00    --   74.00  76.00 148.48  108
 23  \w     41.00 150.00   1.00    4.00    --   74.00  77.00 -45.65  109
 24  \w     69.00 178.00   1.00    4.00    --  101.41  77.00 150.00  109
 25  \w     69.00 178.00   1.00    4.00    --  101.41  77.00 -90.00  109
 26  \w     69.00 178.00   1.00    4.00    --  101.41  77.00-150.00  109
 27  \w     69.00 178.00   1.00    4.00    --  101.41  77.00   0.00  109
 28  \w     28.00 117.00   1.00    4.00    --  101.41-125.00-150.00   89
 29  \w     69.00 178.00   1.00    4.00    --  101.41  77.00-120.00  109
 30  \w     69.00 178.00   1.00    4.00    --  101.41  77.00  90.00  109
 31  \w     28.00 117.00   1.00    4.00    --  101.41-125.00  30.00   89
 32  \w     69.00 178.00   1.00    4.00    --  101.41  77.00 -60.00  109
 33  \w     69.00 178.00   1.00    4.00    --  101.41  77.00 -30.00  109
 34  \w     69.00 178.00   1.00    4.00    --  101.41  77.00-180.00  109
 35  \w     69.00 178.00   1.00    4.00    --  101.41  77.00 120.00  109
 36  \w     69.00 178.00   1.00    4.00    --  101.41  77.00  30.00  109
 37  \w     94.00 175.00   1.00    4.00    --  101.41 125.00   0.00   81
 38  \w     25.00 134.00   1.00    4.00    --  101.41 -77.00  30.00  109
 39  \w     69.00 178.00   1.00    4.00    --  101.41  77.00  60.00  109
 40  \w     28.00 117.00   1.00    4.00    --  101.41-125.00 -30.00   89
 41  \w     17.00  45.00   1.00    1.00    --   50.00  80.00 103.76   28
 42  \w     17.00  45.00   1.00    1.00    --   50.00  80.00 -85.94   28
 43  \w     17.00  45.00   1.00    1.00    --   50.00  80.00   8.73   28
 44  \w     26.00 134.00   1.00    1.00    --   58.00  76.00  -4.69  108
 45  \w     26.00 133.00   1.00    1.00    --   58.00  75.00-131.23  107
 46  \w     30.00 138.00   1.00    1.00    --   62.00  76.00 173.91  108
 47  \w     34.00 142.00   1.00    1.00    --   66.00  76.00 117.99  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0932085000
_diffrn_orient_matrix_UB_12      0.1284919000
_diffrn_orient_matrix_UB_13      -0.0363999000
_diffrn_orient_matrix_UB_21      -0.1416264000
_diffrn_orient_matrix_UB_22      0.0843534000
_diffrn_orient_matrix_UB_23      0.0062106000
_diffrn_orient_matrix_UB_31      -0.0167338000
_diffrn_orient_matrix_UB_32      -0.0111458000
_diffrn_orient_matrix_UB_33      0.1181839000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            33371
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.919
_diffrn_reflns_theta_min         3.552
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.136
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.477
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4716
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0532P)^2^+0.5698P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4422
_reflns_number_total             4716
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02963_si_002.cif
_cod_data_source_block           rok76
_cod_original_cell_volume        1233.50(3)
_cod_database_code               4037890
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c27 h23 n3 o3 s1 Se1'
_shelx_estimated_absorpt_t_max   0.705
_shelx_estimated_absorpt_t_min   0.303
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C22-O3 \\sim C22-O4
 with sigma of 0.01
 O3-C27 \\sim O4-C28
 with sigma of 0.01
3. Others
 Fixed Sof: O3(0.75) O4(0.25) C27(0.75) H27A(0.75) H27B(0.75) H27C(0.75)
 C28(0.25) H28A(0.25) H28B(0.25) H28C(0.25)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C24(H24)
4.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C)
;
_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 1.691
_oxdiff_exptl_absorpt_empirical_full_min 0.601