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_7246869
_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         'C7 H8 N5 Se, Cl, H2 O'
_chemical_formula_sum            'C7 H10 Cl N5 O Se'
_chemical_formula_weight         294.61
_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   mixed
_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                 111.161(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8986(15)
_cell_length_b                   14.662(4)
_cell_length_c                   9.851(4)
_cell_measurement_reflns_used    7990
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      33.092
_cell_measurement_theta_min      2.615
_cell_volume                     1063.9(6)
_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      100.00
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7772
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.152
_diffrn_reflns_theta_min         2.616
_exptl_absorpt_coefficient_mu    3.762
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.3370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1109 before and 0.0463 after correction.
The Ratio of minimum to maximum transmission is 0.4514.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.839
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         1.549
_refine_diff_density_min         -1.657
_refine_diff_density_rms         0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         3987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0387
_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^)+(0.0513P)^2^+0.9974P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1063
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3434
_reflns_number_total             3987
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00385j2.cif
_cod_data_source_block           mo_21kub116_0m_a
_cod_depositor_comments
'Adding full bibliography for 7246868--7246875.cif.'
_cod_database_code               7246869
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.315
_shelx_estimated_absorpt_t_min   0.211
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.c X=CH2 refined with riding coordinates:
 N4(H4A,H4B), N5(H5A,H5B)
;
_shelx_res_checksum              76998
_olex2_submission_special_instructions 'No special instructions were received'