Construction of 2H-1,4-selenazin-3(4H)-one framework via cyclization of pyrazole derivatives bearing chloroacetamide and selenocyanate fragments
Kudryavtseva, Tatiana A.; Kudryavtseva, Ekaterina; Lichitsky, Boris V.; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D6OB00263C

data_7161113
_publ_section_title
;
 Construction of a 2<i>H</i>-1,4-selenazin-3(4<i>H</i>)-one framework
 <i>via</i> cyclization of pyrazole derivatives bearing chloroacetamide
 and selenocyanate fragments.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3748
_journal_page_last               3758
_journal_paper_doi               10.1039/d6ob00263c
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C14 H15 N3 O Se'
_chemical_formula_sum            'C14 H15 N3 O Se'
_chemical_formula_weight         320.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2025-05-01
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2025-11-27 deposited with the CCDC.	2026-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.193(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8853(3)
_cell_length_b                   7.8504(3)
_cell_length_c                   21.1466(9)
_cell_measurement_reflns_used    9752
_cell_measurement_temperature    291.0
_cell_measurement_theta_max      31.50
_cell_measurement_theta_min      2.71
_cell_volume                     1307.00(9)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      291.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            50591
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.547
_diffrn_reflns_theta_min         2.768
_exptl_absorpt_coefficient_mu    2.868
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.5646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0821 before and 0.0573 after correction.
The Ratio of minimum to maximum transmission is 0.7566.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.319
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         4373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0225
_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^)+(0.0227P)^2^+0.8340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0528
_refine_ls_wR_factor_ref         0.0556
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3854
_reflns_number_total             4373
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00263c2.cif
_cod_data_source_block           TK-401
_cod_depositor_comments          'Adding full bibliography for 7161113.cif.'
_cod_database_code               7161113
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.904
_shelx_estimated_absorpt_t_min   0.461
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C15(H15)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              75863
_olex2_submission_special_instructions 'No special instructions were received'