The synthesis and crystal structure of 2-(chloroselanyl)pyridine 1-oxide: the first monomeric organoselenenyl chloride stabilized by an intramolecular secondary Se···O interaction
Askerov, Rizvan K.; Matsulevich, Zhanna V.; Borisova, Galina N.; Zalepkina, Svetlana A.; Smirnov, Vasiliy F.; Grishina, Maria M.; Dorovatovskii, Pavel V.; Borisov, Alexander V.; Khrustalev, Victor N.; Acta Crystallographica Section E 72 (2016) 1864–1866; doi:10.1107/S2056989016018946

data_2241971
_publ_section_title
;
 The synthesis and crystal structure of 2-(chloroselanyl)pyridine 1-oxide:
 the first monomeric organoselenenyl chloride stabilized by an
 intramolecular secondary Se&#x00B7;&#x00B7;&#x00B7;O interaction
;
_journal_coeditor_code           SU5337
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1864
_journal_page_last               1866
_journal_paper_doi               10.1107/S2056989016018946
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C5 H4 Cl N O Se'
_chemical_formula_moiety         'C5 H4 Cl N O Se'
_chemical_formula_sum            'C5 H4 Cl N O Se'
_chemical_formula_weight         208.50
_chemical_name_systematic
;
2-(Chloroselanyl)pyridine 1-oxide
;
_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   geom
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 94.32(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9601(8)
_cell_length_b                   7.5102(15)
_cell_length_c                   22.350(5)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.0
_cell_measurement_theta_min      5.0
_cell_volume                     662.8(2)
_computing_cell_refinement
;
<i>iMosflm</i> (Battye <i>et al.</i>, 2011)
;
_computing_data_collection
;
<i>Automar</i> (MarXperts, 2015)
;
_computing_data_reduction
;
<i>iMosflm</i> (Battye <i>et al.</i>, 2011)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL-2014/6 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'Rayonix SX-165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.96990
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5526
_diffrn_reflns_theta_full        35.587
_diffrn_reflns_theta_max         38.083
_diffrn_reflns_theta_min         4.993
_exptl_absorpt_coefficient_mu    13.675
_exptl_absorpt_correction_T_max  0.660
_exptl_absorpt_correction_T_min  0.550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SCALA</i>; Evans, 2006)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.089
_exptl_crystal_description       prism
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.263
_refine_diff_density_min         -1.579
_refine_ls_extinction_coef       0.054(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1310
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0741
_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^)+(0.06P)^2^+1.6P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1633
_refine_ls_wR_factor_ref         0.1753
_reflns_number_gt                1121
_reflns_number_total             1310
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            su5337sup1.cif
_cod_data_source_block           I
_cod_database_code               2241971
_cod_database_fobs_code          2241971
_shelx_estimated_absorpt_t_min   0.549
_shelx_estimated_absorpt_t_max   0.685
_shelx_hkl_checksum              66329
_shelx_res_checksum              71765
_shelxl_version_number           2014/6