Mechanistic investigation of 1,3-dipolar cycloaddition between bifunctional 2-pyridylselenyl reagents and nitriles including reactions with cyanamides
Artemjev, Alexey A.; Kubasov, Alexey S.; Kuznetsov, Maxim L.; Grudova, Mariya V.; Khrustalev, Victor N.; Kritchenkov, Andreii S.; Tskhovrebov, Alexander G.; CrystEngComm 25 (2023) 3691–3701; doi:10.1039/D3CE00385J

data_7246872
_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         'C9 H11 N4 Se, Cl'
_chemical_formula_sum            'C9 H11 Cl N4 Se'
_chemical_formula_weight         289.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/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                 108.226(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.922(4)
_cell_length_b                   6.546(3)
_cell_length_c                   14.620(5)
_cell_measurement_reflns_used    3470
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.973
_cell_measurement_theta_min      2.939
_cell_volume                     1083.7(7)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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      100.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6556
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.023
_diffrn_reflns_theta_min         2.934
_exptl_absorpt_coefficient_mu    3.682
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.4174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1273 before and 0.0486 after correction.
The Ratio of minimum to maximum transmission is 0.5595.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.775
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.739
_refine_diff_density_min         -1.074
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         3107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0338
_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^)+(0.0315P)^2^+1.3213P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0888
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2532
_reflns_number_total             3107
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00385j2.cif
_cod_data_source_block           7
_cod_depositor_comments
'Adding full bibliography for 7246868--7246875.cif.'
_cod_database_code               7246872
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.710
_shelx_estimated_absorpt_t_min   0.216
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              56064
_olex2_submission_special_instructions 'No special instructions were received'