Highly active mesoionic chalcogenone zinc(ii) derivatives for C–S cross-coupling reactions
Vaddamanu, Moulali; Velappan, Kavitha; Prabusankar, Ganesan; New Journal of Chemistry 44 (2020) 129–140; doi:10.1039/C9NJ04440J

data_7059070
_publ_section_title
;
 Highly active mesoionic chalcogenone zinc(ii) derivatives for C--S
 cross-coupling reactions
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              129
_journal_page_last               140
_journal_paper_doi               10.1039/C9NJ04440J
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C20 H13 Cl S'
_chemical_formula_sum            'C20 H13 Cl S'
_chemical_formula_weight         320.84
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-02-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-07 deposited with the CCDC.	2019-11-19 downloaded from the CCDC.
;
_cell_angle_alpha                107.316(7)
_cell_angle_beta                 94.243(6)
_cell_angle_gamma                99.600(6)
_cell_formula_units_Z            2
_cell_length_a                   5.5355(3)
_cell_length_b                   11.3824(10)
_cell_length_c                   13.4351(10)
_cell_measurement_reflns_used    2307
_cell_measurement_temperature    293
_cell_measurement_theta_max      69.1210
_cell_measurement_theta_min      3.4740
_cell_volume                     789.92(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9930
_diffrn_measured_fraction_theta_max 0.9930
_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     32.00  64.00   1.00    1.00    --    0.00  57.00 120.00   32
  2  \w    -20.00   7.00   1.00    1.00    --    0.00  57.00-120.00   27
  3  \w    -22.00  11.00   1.00    1.00    --    0.00  57.00 120.00   33
  4  \w     36.00  63.00   1.00    1.00    --    0.00  57.00-120.00   27
  5  \w     -9.00  60.00   1.00    3.87    --   54.00 -19.00-180.00   69
  6  \w     47.00  80.00   1.00    3.87    --   54.00-125.00  90.00   33
  7  \w     30.00 127.00   1.00    3.87    --   54.00  38.00-180.00   97
  8  \w     -1.00  71.00   1.00    3.87    --   54.00 -57.00 -90.00   72
  9  \w     32.00  95.00   1.00    3.87    --   54.00 -99.00-180.00   63
 10  \w     71.00 103.00   1.00    3.87    --   54.00 -19.00-180.00   32
 11  \w    -11.00  80.00   1.00    3.87    --   54.00 -38.00   0.00   91
 12  \w     54.00 131.00   1.00    3.87    --  108.00 -50.00-150.00   77
 13  \w     67.00  94.00   1.00    3.87    --  108.00-111.00 120.00   27
 14  \w     38.00  75.00   1.00    3.87    --  108.00 -50.00 120.00   37
 15  \w     92.00 128.00   1.00    3.87    --  108.00 -63.00-120.00   36
 16  \w     85.00 170.00   1.00    3.87    --  108.00  50.00  30.00   85
 17  \w     43.00  88.00   1.00    3.87    --  108.00 -91.00 -60.00   45
 18  \w     69.00 141.00   1.00    3.87    --  108.00 178.00 -60.00   72
 19  \w     41.00  73.00   1.00    3.87    --  108.00 -63.00-150.00   32
 20  \w     84.00 124.00   1.00    3.87    --  108.00  63.00  60.00   40
 21  \w     74.00 100.00   1.00    3.87    --  108.00-111.00-120.00   26
 22  \w    129.00 174.00   1.00    3.87    --  108.00  63.00 -30.00   45
 23  \w     42.00  67.00   1.00    3.87    --  108.00-111.00  30.00   25
 24  \w     87.00 112.00   1.00    3.87    --  108.00-111.00  30.00   25
 25  \w    113.00 138.00   1.00    3.87    --  108.00 -77.00  60.00   25
 26  \w    100.00 126.00   1.00    3.87    --  108.00 -12.00  30.00   26
 27  \w     87.00 123.00   1.00    3.87    --  108.00 -50.00   0.00   36
 28  \w    138.00 169.00   1.00    3.87    --  108.00  50.00  90.00   31
 29  \w     37.00 115.00   1.00    3.87    --  108.00  12.00  60.00   78
 30  \w    153.00 178.00   1.00    3.87    --  108.00  12.00  60.00   25
 31  \w     84.00 127.00   1.00    3.87    --  108.00 -63.00 -60.00   43
 32  \w     55.00 103.00   1.00    3.87    --  108.00-111.00  90.00   48
 33  \w    143.00 174.00   1.00    3.87    --  108.00  63.00 -90.00   31
 34  \w     91.00 116.00   1.00    3.87    --  108.00  63.00 -90.00   25
 35  \w    107.00 132.00   1.00    3.87    --  108.00 178.00 -30.00   25
 36  \w     35.00  74.00   1.00    3.87    --  108.00 -12.00  30.00   39
 37  \w     81.00 112.00   1.00    3.87    --  108.00 -50.00 120.00   31
 38  \w     84.00 111.00   1.00    3.87    --  108.00-111.00 -90.00   27
 39  \w     76.00 105.00   1.00    3.87    --  108.00-111.00   0.00   29
 40  \w     80.00 110.00   1.00    3.87    --  108.00-111.00 150.00   30
 41  \w     88.00 113.00   1.00    3.87    --  108.00  50.00  90.00   25
 42  \w     65.00 129.00   1.00    3.87    --  108.00 -63.00  30.00   64
 43  \w    114.00 139.00   1.00    3.87    --  108.00 -91.00 -60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0650454000
_diffrn_orient_matrix_UB_12      0.1417389000
_diffrn_orient_matrix_UB_13      0.0602364000
_diffrn_orient_matrix_UB_21      0.1623172000
_diffrn_orient_matrix_UB_22      0.0209525000
_diffrn_orient_matrix_UB_23      -0.0839040000
_diffrn_orient_matrix_UB_31      -0.2247030000
_diffrn_orient_matrix_UB_32      0.0198197000
_diffrn_orient_matrix_UB_33      -0.0633349000
_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  0.0142
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6327
_diffrn_reflns_theta_full        69.9672
_diffrn_reflns_theta_max         69.97
_diffrn_reflns_theta_min         3.48
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.3488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             334.1556
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.2080
_refine_diff_density_min         -0.2583
_refine_diff_density_rms         0.0364
_refine_ls_d_res_high            0.8206
_refine_ls_d_res_low             12.7152
_refine_ls_goodness_of_fit_ref   1.0425
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0425
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0591P)^2^+0.0967P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1133
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              12
_reflns_limit_k_min              -13
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2458
_reflns_number_total             2976
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9nj04440j2.cif
_cod_data_source_block           E14
_cod_depositor_comments
;Adding full bibliography for 7059065--7059073.cif.

 Adding full bibliography for 7059065--7059073.cif.
;
_cod_database_code               7059070
_chemical_oxdiff_formula         C10H10SF
_reflns_odcompleteness_completeness 92.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C8(H8), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C1A(H1A), C20(H20), C21(H21)
;
_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 1.442
_oxdiff_exptl_absorpt_empirical_full_min 0.690