Copper-catalyzed direct C–H arylselenation of 4-nitro-pyrazoles and other heterocycles with selenium powder and aryl iodides. Access to unsymmetrical heteroaryl selenides
Jakubczyk, Michał; Mkrtchyan, Satenik; Madura, Izabela D.; Marek, Paulina H.; Iaroshenko, Viktor O.; RSC Advances 9 (2019) 25368–; doi:10.1039/C9RA05004C

data_7233383
_publ_section_title
;
 Copper-catalyzed direct C--H arylselenation of 4-nitro-pyrazoles and
 other heterocycles with selenium powder and aryl iodides. Access to
 unsymmetrical heteroaryl selenides
;
_journal_issue                   44
_journal_name_full               'RSC Advances'
_journal_page_first              25368
_journal_paper_doi               10.1039/C9RA05004C
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C16 H13 Br N4 O2 Se'
_chemical_formula_sum            'C16 H13 Br N4 O2 Se'
_chemical_formula_weight         452.17
_chemical_name_systematic
;
3-bromo-2-(1-phenetyl)-4-nitro-1H-pyrazol-3-yl)selanyl)pyridine
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-13
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-13 deposited with the CCDC.    2019-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                83.404(5)
_cell_angle_beta                 89.627(5)
_cell_angle_gamma                60.612(7)
_cell_formula_units_Z            4
_cell_length_a                   7.8948(5)
_cell_length_b                   7.9369(6)
_cell_length_c                   31.3002(16)
_cell_measurement_reflns_used    3359
_cell_measurement_temperature    298(3)
_cell_measurement_theta_max      27.5510
_cell_measurement_theta_min      3.8390
_cell_volume                     1694.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.885
_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    -60.00  43.00   1.00   10.00    --   16.20 -38.00-150.00  103
  2  \w    -60.00  43.00   1.00   10.00    --   16.20 -38.00 -60.00  103
  3  \w     -4.00  58.00   1.00   10.00    --   16.20 -99.00 -90.00   62
  4  \w    -60.00  43.00   1.00   10.00    --   16.20 -38.00  90.00  103
  5  \w     56.00 106.00   1.00   10.00    --   16.20 179.00 -90.00   50
  6  \w    -92.00 -48.00   1.00   10.00    --  -15.89 -38.00-180.00   44
  7  \w    -22.00  31.00   1.00   10.00    --   16.20  93.00  57.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0454220000
_diffrn_orient_matrix_UB_12      0.0402090000
_diffrn_orient_matrix_UB_13      -0.0209495000
_diffrn_orient_matrix_UB_21      -0.0185224000
_diffrn_orient_matrix_UB_22      -0.0785830000
_diffrn_orient_matrix_UB_23      -0.0006253000
_diffrn_orient_matrix_UB_31      -0.0908916000
_diffrn_orient_matrix_UB_32      0.0538868000
_diffrn_orient_matrix_UB_33      0.0091016000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_av_unetI/netI     0.1281
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            24857
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         31.318
_diffrn_reflns_theta_min         3.281
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.590
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            greenish
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         9838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1642
_refine_ls_R_factor_gt           0.0604
_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          0.0631
_refine_ls_wR_factor_ref         0.0860
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4552
_reflns_number_total             9838
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra05004c2.cif
_cod_data_source_block           2f
_cod_database_code               7233383
_shelx_estimated_absorpt_t_max   0.340
_shelx_estimated_absorpt_t_min   0.207
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C23(H23C,H23D), C24(H24C,H24D), C23A(H23A,H23B), C24A(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C16A(H16A), C11A(H11A), C16(H16), C8A(H8A), C7A(H7A), C3(H3), C9A(H9A),
 C15A(H15A), C9(H9), C14(H14), C15(H15), C3A(H3A), C10A(H10A), C14A(H14A),
 C10(H10), C8(H8), C11(H11), C7(H7)
;
_shelx_res_checksum              9334
_olex2_date_sample_data_collection 2018-04-06
_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 1.807
_oxdiff_exptl_absorpt_empirical_full_min 0.760