PdII- and PtII-mediated coupling of aryl isocyanides with N-heterocyclic thiones
Popov, Roman A.; Mikherdov, Alexander S.; Novikov, Alexander S.; Myznikov, Leonid V.; Boyarskiy, Vadim P.; New Journal of Chemistry 45 (2021) 1785–1789; doi:10.1039/D0NJ05386D

data_7060163
_publ_section_title
;
 PdII- and PtII-mediated coupling of aryl isocyanides with N-heterocyclic
 thiones
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1785
_journal_page_last               1789
_journal_paper_doi               10.1039/D0NJ05386D
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C22 H23 Cl N4 Pd S'
_chemical_formula_sum            'C22 H23 Cl N4 Pd S'
_chemical_formula_weight         517.35
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-10-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-15 deposited with the CCDC.	2020-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.298(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9266(2)
_cell_length_b                   12.2058(3)
_cell_length_c                   18.2152(5)
_cell_measurement_reflns_used    11312
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      32.1180
_cell_measurement_theta_min      3.3430
_cell_volume                     2206.96(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_details
;
  1 omega -100.00  -39.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -      -25.4311 -178.0000  -90.0000 61

  2 omega   48.00   95.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       26.5248   57.0000   60.0000 47

  3 omega    3.00   57.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       26.5248  -77.0000  150.0000 54

  4 omega  -51.00   -7.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -      -25.4311  -38.0000 -150.0000 44

  5 omega  -19.00   38.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       26.5248  -99.0000  -90.0000 57

  6 omega   -9.00   17.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -      -25.4311   77.0000   90.0000 26

  7 omega   19.00   44.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       26.5248   77.0000  -30.0000 25

  8 omega  -72.00  -45.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -      -25.4311 -178.0000 -120.0000 27

  9 omega    2.00   99.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       26.5248   38.0000 -180.0000 97

 10 omega   29.00   76.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       26.5248   57.0000    0.0000 47

 11 omega    0.00   33.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       26.5248   85.0000   65.0000 33

 12 omega  -17.00   11.00   1.0000    1.0600
omega____ theta____ kappa____ phi______ frames
    -       26.5248   19.0000  -60.0000 28
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0330335000
_diffrn_orient_matrix_UB_12      -0.0513346000
_diffrn_orient_matrix_UB_13      -0.0028092000
_diffrn_orient_matrix_UB_21      -0.0228750000
_diffrn_orient_matrix_UB_22      -0.0050798000
_diffrn_orient_matrix_UB_23      -0.0367860000
_diffrn_orient_matrix_UB_31      0.0591487000
_diffrn_orient_matrix_UB_32      0.0267547000
_diffrn_orient_matrix_UB_33      -0.0123756000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            29416
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.416
_diffrn_reflns_theta_min         2.790
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_description       prism
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details
;
 Flack x determined using 5695 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     533
_refine_ls_number_reflns         13971
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0197P)^2^+0.1706P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0599
_refine_ls_wR_factor_ref         0.0619
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.848
_reflns_number_gt                13185
_reflns_number_total             13971
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj05386d3.cif
_cod_data_source_block           5a
_cod_depositor_comments
'Adding full bibliography for 7060163--7060166.cif.'
_cod_original_cell_volume        2206.97(10)
_cod_database_code               7060163
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 Cl N4 Pd S'
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H21B(0.021) H15B(0.025) H22A(0.026) H22B(0.026) H22C(0.026)
 H8BA(0.033) H8BB(0.033) H8BC(0.033) H20A(0.021) H20B(0.022) H17D(0.036)
 H17E(0.036) H17F(0.036) H21A(0.02) H22D(0.034) H22E(0.034) H22F(0.034)
 H13A(0.025) H6B(0.024) H18A(0.037) H18B(0.037) H18C(0.037) H8AA(0.051)
 H8AB(0.051) H8AC(0.051) H4B(0.026) H9BA(0.036) H9BB(0.036) H9BC(0.036)
 H5A(0.037) H5B(0.029) H9AA(0.046) H9AB(0.046) H9AC(0.046) H6A(0.035)
 H14B(0.031) H13B(0.027) H17A(0.039) H17B(0.039) H17C(0.039) H14A(0.031)
 H4A(0.038) H18D(0.04) H18E(0.04) H18F(0.04) H15A(0.03)
 Fixed X: H21B(0.096523) H15B(1.094413) H22A(0.104379) H22B(-0.023529)
 H22C(0.107436) H8BA(0.377851) H8BB(0.524003) H8BC(0.486813) H20A(0.700415)
 H20B(-0.051724) H17D(-0.136706) H17E(-0.282171) H17F(-0.234702) H21A(0.553127)
 H22D(0.512501) H22E(0.661894) H22F(0.582168) H13A(-0.43244) H6B(0.613704)
 H18A(1.016715) H18B(0.85894) H18C(0.94375) H8AA(0.318555) H8AB(0.193315)
 H8AC(0.191781) H4B(0.64797) H9BA(0.456726) H9BB(0.439891) H9BC(0.326779) H5A(-
 0.049908) H5B(0.712305) H9AA(0.181464) H9AB(0.151665) H9AC(0.294177)
 H6A(0.023257) H14B(1.103763) H13B(0.951565) H17A(0.739993) H17B(0.771781)
 H17C(0.658492) H14A(-0.510649) H4A(0.042138) H18D(-0.206281) H18E(-0.251925)
 H18F(-0.112216) H15A(-0.411595)
 Fixed Y: H21B(0.280899) H15B(0.503846) H22A(-0.056486) H22B(0.014729)
 H22C(0.030313) H8BA(0.50546) H8BB(0.536137) H8BC(0.413571) H20A(0.695013)
 H20B(0.153594) H17D(0.477004) H17E(0.483684) H17F(0.570891) H21A(0.565)
 H22D(0.841672) H22E(0.813695) H22F(0.90154) H13A(0.350743) H6B(0.544237)
 H18A(0.45643) H18B(0.461853) H18C(0.557383) H8AA(0.484513) H8AB(0.468555)
 H8AC(0.559867) H4B(0.623857) H9BA(0.318087) H9BB(0.424941) H9BC(0.389982)
 H5A(0.206214) H5B(0.646922) H9AA(0.407272) H9AB(0.281524) H9AC(0.321823)
 H6A(0.207587) H14B(0.406527) H13B(0.268865) H17A(0.141884) H17B(0.151483)
 H17C(0.224079) H14A(0.243558) H4A(0.324439) H18D(0.447819) H18E(0.328036)
 H18F(0.348659) H15A(0.252007)
 Fixed Z: H21B(0.580875) H15B(0.490017) H22A(0.735332) H22B(0.751434)
 H22C(0.798755) H8BA(0.720927) H8BB(0.746656) H8BC(0.730711) H20A(0.872334)
 H20B(0.645467) H17D(1.063537) H17E(1.096335) H17F(1.038824) H21A(0.935352)
 H22D(0.727155) H22E(0.748256) H22F(0.793355) H13A(1.046482) H6B(0.442855)
 H18A(0.635989) H18B(0.634443) H18C(0.60043) H8AA(1.072599) H8AB(1.123572)
 H8AC(1.06305) H4B(0.654746) H9BA(0.448549) H9BB(0.401639) H9BC(0.456624)
 H5A(1.005552) H5B(0.534158) H9AA(0.796473) H9AB(0.789824) H9AC(0.815652)
 H6A(0.885724) H14B(0.382082) H13B(0.357811) H17A(0.477317) H17B(0.39335)
 H17C(0.428088) H14A(0.95151) H4A(1.090526) H18D(0.772995) H18E(0.754273)
 H18F(0.792345) H15A(0.837794)
;
_shelx_res_checksum              70978
_olex2_submission_special_instructions 'No special instructions were received'