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#$Date: 2023-07-05 13:07:27 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284917 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/68/7246868.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7246868
loop_
_publ_author_name
'Artemjev, Alexey A.'
'Kubasov, Alexey S.'
'Kuznetsov, Maxim L.'
'Grudova, Mariya V.'
'Khrustalev, Victor N.'
'Kritchenkov, Andreii S.'
'Tskhovrebov, Alexander G.'
_publ_section_title
;
 Mechanistic investigation of 1,3-dipolar cycloaddition between
 bifunctional 2-pyridylselenyl reagents and nitriles including reactions
 with cyanamides
;
_journal_issue                   25
_journal_name_full               CrystEngComm
_journal_page_first              3691
_journal_page_last               3701
_journal_paper_doi               10.1039/D3CE00385J
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C8 H10 N3 Se, Cl'
_chemical_formula_sum            'C8 H10 Cl N3 Se'
_chemical_formula_weight         262.60
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-04-05
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-04-05 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.442(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3227(9)
_cell_length_b                   8.9950(14)
_cell_length_c                   15.321(2)
_cell_measurement_reflns_used    4806
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      30.07
_cell_measurement_theta_min      2.86
_cell_volume                     981.5(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120.00
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5237
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_min         2.264
_exptl_absorpt_coefficient_mu    4.053
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0599 before and 0.0410 after correction.
The Ratio of minimum to maximum transmission is 0.7869.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.241
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.241
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0265
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+2.3209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0648
_refine_ls_wR_factor_ref         0.0689
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1849
_reflns_number_total             1935
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00385j2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7246868--7246875.cif.'
_cod_database_code               7246868
_shelx_shelxl_version_number     2018/3
_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_max   0.961
_shelx_estimated_absorpt_t_min   0.294
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8558(10)
 0.1442(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.71372(6) 0.46833(4) 0.45071(2) 0.01656(11) Uani 1 1 d . . . . .
N1 N 0.6188(5) 0.6210(4) 0.3733(2) 0.0204(7) Uani 1 1 d . . . . .
N2 N 0.7263(4) 0.7479(3) 0.5067(2) 0.0152(6) Uani 1 1 d . . . . .
N3 N 0.5787(5) 0.8812(4) 0.3723(2) 0.0202(7) Uani 1 1 d . . . . .
C1 C 0.7810(5) 0.6109(4) 0.5403(2) 0.0152(7) Uani 1 1 d . . . . .
C2 C 0.8672(5) 0.5946(4) 0.6312(2) 0.0183(8) Uani 1 1 d . . . . .
H2 H 0.905097 0.499135 0.655235 0.022 Uiso 1 1 calc R U . . .
C3 C 0.8966(6) 0.7179(5) 0.6854(3) 0.0217(9) Uani 1 1 d . . . . .
H3 H 0.957192 0.708791 0.747106 0.026 Uiso 1 1 calc R U . . .
C4 C 0.8369(6) 0.8570(4) 0.6491(3) 0.0222(8) Uani 1 1 d . . . . .
H4 H 0.857080 0.942449 0.686563 0.027 Uiso 1 1 calc R U . . .
C5 C 0.7501(6) 0.8717(4) 0.5608(3) 0.0198(8) Uani 1 1 d . . . . .
H5 H 0.706705 0.966110 0.536844 0.024 Uiso 1 1 calc R U . . .
C6 C 0.6414(6) 0.7479(4) 0.4124(2) 0.0185(8) Uani 1 1 d . . . . .
C7 C 0.7179(6) 0.9983(4) 0.3689(3) 0.0258(9) Uani 1 1 d . . . . .
H7A H 0.828691 0.983927 0.418137 0.039 Uiso 1 1 calc R U . . .
H7B H 0.662621 1.095961 0.374695 0.039 Uiso 1 1 calc R U . . .
H7C H 0.754780 0.992766 0.311417 0.039 Uiso 1 1 calc R U . . .
C8 C 0.4465(6) 0.8601(5) 0.2852(3) 0.0251(9) Uani 1 1 d . . . . .
H8A H 0.512504 0.815827 0.242758 0.038 Uiso 1 1 calc R U . . .
H8B H 0.393962 0.956410 0.262171 0.038 Uiso 1 1 calc R U . . .
H8C H 0.344829 0.793826 0.292455 0.038 Uiso 1 1 calc R U . . .
Cl1 Cl 0.88262(15) 0.24025(10) 0.57557(6) 0.0218(2) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Se1 C1 87.53(15) . . ?
C6 N1 Se1 112.0(3) . . ?
C1 N2 C5 121.4(3) . . ?
C1 N2 C6 113.7(3) . . ?
C5 N2 C6 124.9(3) . . ?
C6 N3 C7 118.5(3) . . ?
C6 N3 C8 111.9(3) . . ?
C8 N3 C7 112.0(3) . . ?
N2 C1 Se1 109.9(3) . . ?
N2 C1 C2 119.9(3) . . ?
C2 C1 Se1 130.1(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.3(4) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.5(4) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.9(4) . . ?
C5 C4 H4 119.6 . . ?
N2 C5 H5 120.5 . . ?
C4 C5 N2 119.0(4) . . ?
C4 C5 H5 120.5 . . ?
N1 C6 N2 116.7(3) . . ?
N1 C6 N3 125.1(3) . . ?
N3 C6 N2 118.1(3) . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 N1 1.842(3) . ?
Se1 C1 1.860(4) . ?
N1 C6 1.282(5) . ?
N2 C1 1.360(5) . ?
N2 C5 1.374(5) . ?
N2 C6 1.434(5) . ?
N3 C6 1.376(5) . ?
N3 C7 1.475(5) . ?
N3 C8 1.468(5) . ?
C1 C2 1.396(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.372(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.361(6) . ?
C5 H5 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se1 N1 C6 N2 -2.4(5) . . . . ?
Se1 N1 C6 N3 -177.6(3) . . . . ?
Se1 C1 C2 C3 -177.6(3) . . . . ?
N1 Se1 C1 N2 1.3(3) . . . . ?
N1 Se1 C1 C2 178.7(4) . . . . ?
N2 C1 C2 C3 -0.4(6) . . . . ?
C1 Se1 N1 C6 0.6(3) . . . . ?
C1 N2 C5 C4 2.5(6) . . . . ?
C1 N2 C6 N1 3.5(5) . . . . ?
C1 N2 C6 N3 179.0(3) . . . . ?
C1 C2 C3 C4 1.1(6) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C3 C4 C5 N2 -1.8(6) . . . . ?
C5 N2 C1 Se1 176.2(3) . . . . ?
C5 N2 C1 C2 -1.5(5) . . . . ?
C5 N2 C6 N1 -175.5(4) . . . . ?
C5 N2 C6 N3 0.1(6) . . . . ?
C6 N2 C1 Se1 -2.8(4) . . . . ?
C6 N2 C1 C2 179.5(3) . . . . ?
C6 N2 C5 C4 -178.5(4) . . . . ?
C7 N3 C6 N1 -120.0(4) . . . . ?
C7 N3 C6 N2 64.9(5) . . . . ?
C8 N3 C6 N1 12.7(6) . . . . ?
C8 N3 C6 N2 -162.5(3) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8558(10)
2 0.1442(10)
