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_7246874
_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         'C16 H12 N3 Se, Cl'
_chemical_formula_sum            'C16 H12 Cl N3 Se'
_chemical_formula_weight         360.70
_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_Hall           'P 4w'
_space_group_name_H-M_alt        'P 41'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.811(4)
_cell_length_b                   7.811
_cell_length_c                   23.699(8)
_cell_measurement_reflns_used    8786
_cell_measurement_temperature    300.0
_cell_measurement_theta_max      30.580
_cell_measurement_theta_min      2.611
_cell_volume                     1445.9(9)
_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      300(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12885
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_min         2.608
_exptl_absorpt_coefficient_mu    2.777
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.5204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0907 before and 0.0709 after correction.
The Ratio of minimum to maximum transmission is 0.6973.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.682
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 1420 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.040(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3287
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0331
_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/[\s^2^(Fo^2^)+(0.0363P)^2^+0.8187P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0866
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3136
_reflns_number_total             3287
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00385j2.cif
_cod_data_source_block           mo_21kub178_0m_a
_cod_depositor_comments
'Adding full bibliography for 7246868--7246875.cif.'
_cod_original_cell_volume        1445.9(14)
_cod_database_code               7246874
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.403
_shelx_estimated_absorpt_t_min   0.287
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C3(H3A), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C12(H12),
 C13(H13), C14(H14), C15(H15)
;
_shelx_res_checksum              29698
_olex2_submission_special_instructions 'No special instructions were received'