Electrochemical synthesis of versatile ammonium oxides under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions.
Yuan, Yong; Li, Liang-Sen; Zhang, Lin; Wang, Feng; Jiang, Lin; Zuo, Lin; Wang, Qi; Hu, Jian-Guo; Lei, Aiwen; Chemical communications (Cambridge, England) 57 (2021) 2768–2771; doi:10.1039/d1cc00486g

data_7127977
_publ_section_title
;
 Electrochemical synthesis of versatile ammonium oxides under metal
 catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions.
;
_journal_issue                   22
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2768
_journal_page_last               2771
_journal_paper_doi               10.1039/d1cc00486g
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H14 N2 O S'
_chemical_formula_sum            'C16 H14 N2 O S'
_chemical_formula_weight         282.37
_chemical_name_systematic
5-methyl-2-phenyl-4-(phenylthio)-1,2-dihydro-3H-pyrazol-3-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_Int_Tables_number      7
_atom_sites_solution_primary     dual
_audit_creation_date             2020-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-29 deposited with the CCDC.	2021-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.244(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6728(6)
_cell_length_b                   6.3539(3)
_cell_length_c                   11.8458(6)
_cell_measurement_reflns_used    4567
_cell_measurement_temperature    295
_cell_measurement_theta_max      27.1790
_cell_measurement_theta_min      4.0640
_cell_volume                     714.07(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9932
_diffrn_measured_fraction_theta_max 0.9932
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -85.00   3.00   1.00    5.05    --  -15.92 -37.00 -90.00   88
  2  \w    -87.00  13.00   1.00    5.05    --  -15.92 -19.00 -60.00  100
  3  \w    -35.00  53.00   1.00    5.05    --  -15.92  37.00  90.00   88
  4  \w     34.00  89.00   1.00    5.05    --   16.70-178.00   0.00   55
  5  \w    -20.00  56.00   1.00    5.05    --   16.70 -99.00   0.00   76
  6  \w    -20.00  56.00   1.00    5.05    --   16.70 -99.00-150.00   76
  7  \w      0.00  25.00   1.00    5.05    --   16.70  57.00-120.00   25
  8  \w      0.00  84.00   1.00    5.05    --   16.70  57.00 150.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0563231000
_diffrn_orient_matrix_UB_12      0.0723016000
_diffrn_orient_matrix_UB_13      0.0022566000
_diffrn_orient_matrix_UB_21      0.0478562000
_diffrn_orient_matrix_UB_22      -0.0761687000
_diffrn_orient_matrix_UB_23      0.0287544000
_diffrn_orient_matrix_UB_31      0.0113553000
_diffrn_orient_matrix_UB_32      -0.0376448000
_diffrn_orient_matrix_UB_33      -0.0538418000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9070
_diffrn_reflns_theta_full        24.9970
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.51
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ??
_exptl_crystal_density_diffrn    1.3132
_exptl_crystal_description       block
_exptl_crystal_F_000             296.3588
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ????'
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.1180
_refine_diff_density_min         -0.1489
_refine_diff_density_rms         0.0314
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.07(7)
_refine_ls_d_res_high            0.8410
_refine_ls_d_res_low             5.8092
_refine_ls_goodness_of_fit_ref   1.0660
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2496
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.0660
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0413P)^2^+0.0214P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0761
_reflns_Friedel_coverage         0.988
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              7
_reflns_limit_k_min              -7
_reflns_limit_l_max              13
_reflns_limit_l_min              -14
_reflns_number_gt                2393
_reflns_number_total             2496
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1cc00486g2.cif
_cod_data_source_block           LS2020072701
_cod_depositor_comments          'Adding full bibliography for 7127977.cif.'
_cod_original_sg_symbol_Hall     ' P -2yc'
_cod_database_code               7127977
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C20(H20), C16(H16), C19(H19), C1(H1), C3(H3), C2(H2), C5(H5), C4(H4)
2.b Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.288
_oxdiff_exptl_absorpt_empirical_full_min 0.593