Convenient synthesis of thiolated 2,7-disubstituted tropones <i>via</i> double C-N bond cleavage of tropinone derivatives.
Huang, Lei; Wang, Yan; Liu, Xin; Tian, Shi-Kai; Organic & biomolecular chemistry 21 (2023) 9321–9325; doi:10.1039/d3ob01835k

data_7159684
_publ_section_title
;
 Convenient synthesis of thiolated 2,7-disubstituted tropones <i>via</i>
 double C-N bond cleavage of tropinone derivatives.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9321
_journal_page_last               9325
_journal_paper_doi               10.1039/d3ob01835k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C F3 O3 S, C24 H26 N O'
_chemical_formula_sum            'C25 H26 F3 N O4 S'
_chemical_formula_weight         493.53
_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   geom
_audit_creation_date             2023-04-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-05-02 deposited with the CCDC.	2023-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.2304(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2016(2)
_cell_length_b                   16.5260(2)
_cell_length_c                   11.22516(19)
_cell_measurement_reflns_used    5373
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.8960
_cell_measurement_theta_min      3.9880
_cell_volume                     2745.15(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_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   -115.00 -22.00   1.00    3.00    --  -41.76 -57.00-150.00   93
  2  \w    -62.00  31.00   1.00    3.00    --  -41.76  38.00-180.00   93
  3  \w     39.00  71.00   1.00    3.00    --   41.76 -99.00-180.00   32
  4  \w    152.00 178.00   1.00    6.00    --  106.05  77.00   0.00   26
  5  \w     42.00 112.00   1.00    6.00    --  106.05-125.00 120.00   70
  6  \w     87.00 175.00   1.00    6.00    --  106.05  30.00  30.00   88
  7  \w     59.00  85.00   1.00    6.00    --  106.05-125.00-180.00   26
  8  \w     32.00 133.00   1.00    6.00    --  106.05 -30.00-150.00  101
  9  \w     41.00 138.00   1.00    6.00    --  106.05 -77.00  90.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0772890000
_diffrn_orient_matrix_UB_12      0.0020908000
_diffrn_orient_matrix_UB_13      -0.1158262000
_diffrn_orient_matrix_UB_21      -0.0689590000
_diffrn_orient_matrix_UB_22      0.0114991000
_diffrn_orient_matrix_UB_23      0.0800447000
_diffrn_orient_matrix_UB_31      0.0103061000
_diffrn_orient_matrix_UB_32      0.0924904000
_diffrn_orient_matrix_UB_33      -0.0073906000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10398
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.989
_diffrn_reflns_theta_min         4.010
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.474
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5335
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0793P)^2^+0.6118P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1484
_refine_ls_wR_factor_ref         0.1555
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4538
_reflns_number_total             5335
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01835k2.cif
_cod_data_source_block           hl-1_autored
_cod_depositor_comments
'Adding full bibliography for 7159683--7159684.cif.'
_cod_database_code               7159684
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         c20h20o2s1f3
_shelx_estimated_absorpt_t_max   0.820
_shelx_estimated_absorpt_t_min   0.737
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C6(H6)
1.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
1.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C15(H15), C8(H8), C14(H14), C11(H11), C17(H17), C12(H12),
 C13(H13), C21(H21), C18(H18), C19(H19), C20(H20), C10(H10)
1.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              61312
_shelx_fab_checksum              6168
_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 1.238
_oxdiff_exptl_absorpt_empirical_full_min 0.789