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#$Date: 2025-08-19 21:17:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301807 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/19/2241971.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2241971
loop_
_publ_author_name
'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.'
_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···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
;
iMosflm (Battye et al., 2011)
;
_computing_data_collection
;
Automar (MarXperts, 2015)
;
_computing_data_reduction
;
iMosflm (Battye et al., 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
;
(SCALA; 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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.06P)²+1.6P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            su5337sup1.cif
_cod_data_source_block           I
_cod_database_code               2241971
_cod_database_fobs_code          2241971
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.549
_shelx_estimated_absorpt_t_max   0.685
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Se Se1 0.51523(13) 0.26936(7) 0.34782(2) 0.02716(17) Uani d 1
Cl Cl1 0.4514(3) 0.18592(14) 0.44303(4) 0.0331(3) Uani d 1
O O1 0.6571(9) 0.4577(4) 0.26942(12) 0.0347(8) Uani d 1
N N1 0.7603(10) 0.5643(5) 0.31523(14) 0.0290(8) Uani d 1
C C2 0.7093(11) 0.4927(5) 0.36941(16) 0.0266(9) Uani d 1
C C3 0.7969(12) 0.5838(6) 0.42160(17) 0.0301(10) Uani d 1
H H3 0.7578 0.5342 0.4596 0.036 Uiso calc 1
C C4 0.9449(14) 0.7515(6) 0.4172(2) 0.0334(13) Uani d 1
H H4 1.0115 0.8173 0.4524 0.040 Uiso calc 1
C C5 0.9941(12) 0.8213(7) 0.36099(19) 0.0343(12) Uani d 1
H H5 1.0906 0.9365 0.3579 0.041 Uiso calc 1
C C6 0.9047(14) 0.7257(5) 0.3095(2) 0.0317(12) Uani d 1
H H6 0.9436 0.7720 0.2710 0.038 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0130 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0210 0.0120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.2300 0.2930 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -3.9380 3.7680 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 Se1 Cl1 94.48(11)
O1 N1 C6 124.8(3)
O1 N1 C2 112.9(3)
C6 N1 C2 122.3(4)
N1 C2 C3 121.0(4)
N1 C2 Se1 102.1(3)
C3 C2 Se1 136.9(3)
C2 C3 C4 118.0(4)
C2 C3 H3 121.0
C4 C3 H3 121.0
C5 C4 C3 119.6(4)
C5 C4 H4 120.2
C3 C4 H4 120.2
C6 C5 C4 120.9(4)
C6 C5 H5 119.6
C4 C5 H5 119.6
N1 C6 C5 118.1(4)
N1 C6 H6 120.9
C5 C6 H6 120.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Se1 C2 1.892(4)
Se1 Cl1 2.2506(11)
O1 N1 1.339(4)
N1 C6 1.350(6)
N1 C2 1.354(5)
C2 C3 1.374(6)
C3 C4 1.395(6)
C3 H3 0.9500
C4 C5 1.389(7)
C4 H4 0.9500
C5 C6 1.381(6)
C5 H5 0.9500
C6 H6 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C6 H6 O1 2_755 0.95 2.34 3.101(6) 137
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 N1 C2 C3 -179.4(4)
C6 N1 C2 C3 1.4(7)
O1 N1 C2 Se1 0.7(4)
C6 N1 C2 Se1 -178.5(4)
Cl1 Se1 C2 N1 -179.0(3)
Cl1 Se1 C2 C3 1.0(5)
N1 C2 C3 C4 -1.0(7)
Se1 C2 C3 C4 178.9(4)
C2 C3 C4 C5 0.9(7)
C3 C4 C5 C6 -1.3(8)
O1 N1 C6 C5 179.2(4)
C2 N1 C6 C5 -1.7(7)
C4 C5 C6 N1 1.6(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139088242
