Iodine-Catalyzed Selenylation of 2<i>H</i>-Indazole.
Dey, Amrita; Hajra, Alakananda; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02199

data_4033627
_publ_section_title
;
 Iodine-Catalyzed Selenylation of 2<i>H</i>-Indazole.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02199
_journal_year                    2019
_chemical_formula_moiety         'C19 H13 Cl N2 Se'
_chemical_formula_sum            'C19 H13 Cl N2 Se'
_chemical_formula_weight         383.72
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                117.878(2)
_cell_angle_beta                 91.349(2)
_cell_angle_gamma                98.247(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3670(4)
_cell_length_b                   9.7630(5)
_cell_length_c                   10.3133(5)
_cell_measurement_reflns_used    13295
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.299
_cell_measurement_theta_min      2.380
_cell_volume                     820.63(7)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13295
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.299
_diffrn_reflns_theta_min         2.380
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.450
_exptl_absorpt_correction_T_max  0.610
_exptl_absorpt_correction_T_min  0.481
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tetragonal
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.856
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.856
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0309
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1104
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3470
_reflns_number_total             4075
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02199_si_002.cif
_cod_data_source_block           1350RKM_A_0m_a
_cod_original_cell_volume        820.64(7)
_cod_database_code               4033627
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              52045
_shelx_hkl_checksum              18033