A convenient stereoselective access to novel 1,2,4-triazepan-3-ones/thiones via reduction or reductive alkylation of 7-membered cyclic semicarbazones and thiosemicarbazones.
Fesenko, Anastasia A.; Grigoriev, Mikhail S.; Shutalev, Anatoly D.; Organic & biomolecular chemistry 16 (2018) 8072–8089; doi:10.1039/c8ob01766b

data_7156500
_publ_section_title
;
 A convenient stereoselective access to novel
 1,2,4-triazepan-3-ones/thiones via reduction or reductive alkylation of
 7-membered cyclic semicarbazones and thiosemicarbazones.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8072
_journal_page_last               8089
_journal_paper_doi               10.1039/c8ob01766b
_journal_volume                  16
_journal_year                    2018
_chemical_formula_sum            'C7 H15 N3 S'
_chemical_formula_weight         173.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2018-01-24 deposited with the CCDC.
2018-10-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.245(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6889(7)
_cell_length_b                   20.404(2)
_cell_length_c                   6.7943(7)
_cell_measurement_reflns_used    3208
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.06
_cell_measurement_theta_min      3.12
_cell_volume                     906.19(16)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6245
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         4.290
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       fragment
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.160
_refine_diff_density_max         1.387
_refine_diff_density_min         -1.721
_refine_diff_density_rms         0.134
_refine_ls_abs_structure_details
;
 Flack x determined using 1376 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.62(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3940
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0707
_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^)+(0.0003P)^2^+5.7898P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1534
_refine_ls_wR_factor_ref         0.1693
_reflns_Friedel_coverage         0.886
_reflns_Friedel_fraction_full    0.918
_reflns_Friedel_fraction_max     0.915
_reflns_number_gt                3277
_reflns_number_total             3940
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01766b2.cif
_cod_data_source_block           No_13_LT
_cod_depositor_comments
'Adding full bibliography for 7156500--7156504.cif.'
_cod_database_code               7156500
_shelx_estimated_absorpt_t_min   0.889
_shelx_estimated_absorpt_t_max   0.954
_shelxl_version_number           2014-3
_shelx_res_checksum              46793