Bromination of bis(pyridin-2-yl) diselenide in methylene chloride: the reaction mechanism and crystal structures of 1<i>H</i>-pyridine-2-selenenyl dibromide and its cycloadduct with cyclopentene (3a<i>SR</i>,9a<i>RS</i>)-2,3,3a,9a-tetrahydro-1<i>H</i>-cyclopenta[4,5][1,3]selenazolo[3,2-<i>a</i>]pyridinium bromide
Matsulevich, Zhanna V.; Lukiyanova, Julia M.; Naumov, Vladimir I.; Borisova, Galina N.; Osmanov, Vladimir K.; Borisov, Alexander V.; Grishina, Maria M.; Khrustalev, Victor N.; Acta Crystallographica Section E 75 (2019) 675–679; doi:10.1107/S2056989019004997

data_2242913
_publ_section_title
;
 Bromination of bis(pyridin-2-yl) diselenide in methylene chloride: the
 reaction mechanism and crystal structures of
 1<i>H</i>-pyridine-2-selenenyl dibromide and its cycloadduct with
 cyclopentene
 (3a<i>SR</i>,9a<i>RS</i>)-2,3,3a,9a-tetrahydro-1<i>H</i>-cyclopenta[4,5][1,3]selenazolo[3,2-<i>a</i>]pyridinium
 bromide
;
_journal_coeditor_code           YK2121
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              675
_journal_page_last               679
_journal_paper_doi               10.1107/S2056989019004997
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C5 H5 Br2 N Se'
_chemical_formula_moiety         'C5 H5 Br2 N Se'
_chemical_formula_sum            'C5 H5 Br2 N Se'
_chemical_formula_weight         317.86
_chemical_name_common
;
1<i>H</i>-Pyridine-2-selenenyl dibromide
;
_chemical_name_systematic
;
Dibromo(pyridin-1-ium-2-yl)selanide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2015
_cell_angle_alpha                90
_cell_angle_beta                 114.9750(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0971(6)
_cell_length_b                   12.6116(10)
_cell_length_c                   8.7325(7)
_cell_measurement_reflns_used    4271
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.61
_cell_measurement_theta_min      2.78
_cell_volume                     808.36(11)
_computing_cell_refinement
;
SAINT (Bruker, 2002)
;
_computing_data_collection
;
APEX2 (Bruker, 2005)
;
_computing_data_reduction
;
SAINT (Bruker, 2002)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXTL (Sheldrick, 2008)
;
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12425
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.624
_diffrn_reflns_theta_min         2.775
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    14.444
_exptl_absorpt_correction_T_max  0.104
_exptl_absorpt_correction_T_min  0.063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.612
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.365
_refine_diff_density_min         -1.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         2959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0302P)^2^+0.5977P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0740
_reflns_number_gt                2426
_reflns_number_total             2959
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yk2121sup1.cif
_cod_data_source_block           1
_cod_database_code               2242913
_shelx_estimated_absorpt_t_min   0.160
_shelx_estimated_absorpt_t_max   0.221
_shelx_hkl_checksum              28136
_shelx_res_checksum              97935
_shelxl_version_number           .2013
_cod_database_fobs_code 2242913