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_2242914
_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          'C10 H12 N Se +, Br -'
_chemical_formula_moiety         'C10 H12 N Se +, Br -'
_chemical_formula_sum            'C10 H12 Br N Se'
_chemical_formula_weight         305.07
_chemical_name_common
;
(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
;
_chemical_name_systematic
;
7-Selena-1\l^5^-azatricyclo[6.4.0.0^2,6^]dodeca-1(12),8,10-trien-1-ylium
bromide
;
_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     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2015
_cell_angle_alpha                111.3500(10)
_cell_angle_beta                 93.657(2)
_cell_angle_gamma                93.5430(10)
_cell_formula_units_Z            2
_cell_length_a                   6.3333(5)
_cell_length_b                   9.0515(7)
_cell_length_c                   9.5807(7)
_cell_measurement_reflns_used    4390
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.65
_cell_measurement_theta_min      2.29
_cell_volume                     508.35(7)
_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 0.994
_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  0.0291
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.671
_diffrn_reflns_theta_min         2.292
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    7.574
_exptl_absorpt_correction_T_max  0.154
_exptl_absorpt_correction_T_min  0.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.993
_exptl_crystal_description       prism
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.644
_refine_diff_density_min         -1.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         3711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0431P)^2^+0.1817P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0803
_reflns_number_gt                3156
_reflns_number_total             3711
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yk2121sup1.cif
_cod_data_source_block           2
_cod_database_code               2242914
_cod_database_fobs_code          2242914
_shelx_estimated_absorpt_t_min   0.210
_shelx_estimated_absorpt_t_max   0.313
_shelx_hkl_checksum              92254
_shelx_res_checksum              93060
_shelxl_version_number           .2013