Regio- and Stereoselective 1,3-Dipolar Cycloaddition of Cyclic Azomethine Imines to Platinum(IV)-Bound Nitriles Giving Δ(2)-1,2,4-Triazoline Species.
Smirnov, Andrey S.; Kritchenkov, Andreii S.; Bokach, Nadezhda A.; Kuznetsov, Maxim L.; Selivanov, Stanislav I.; Gurzhiy, Vladislav V.; Roodt, Andreas; Kukushkin, Vadim Yu; Inorganic chemistry 54 (2015) 11018–11030; doi:10.1021/acs.inorgchem.5b02246

data_4346856
_publ_section_title
;
 Regio- and Stereoselective 1,3-Dipolar Cycloaddition of Cyclic Azomethine
 Imines to Platinum(IV)-Bound Nitriles Giving \D(2)-1,2,4-Triazoline
 Species.
;
_journal_issue                   22
_journal_name_full               'Inorganic chemistry'
_journal_page_first              11018
_journal_page_last               11030
_journal_paper_doi               10.1021/acs.inorgchem.5b02246
_journal_volume                  54
_journal_year                    2015
_chemical_formula_moiety         'C31 H33 Cl2 N5 O3 Pt, C H4 O'
_chemical_formula_sum            'C32 H37 Cl2 N5 O4 Pt'
_chemical_formula_weight         821.65
_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   mixed
_audit_creation_date             2015-05-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.1755(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.73181(15)
_cell_length_b                   25.6039(2)
_cell_length_c                   11.70321(11)
_cell_measurement_reflns_used    26220
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1650
_cell_measurement_theta_min      3.4300
_cell_volume                     3358.64(6)
_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, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -77.00  -51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000  120.0000 26

  2 omega  -73.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   77.0000 -180.0000 99

  3 omega  -50.00   18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000    0.0000 68

  4 omega  -90.00  -24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000  -30.0000 66

  5 omega  -26.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -90.0000 62

  6 omega  -36.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000   90.0000 25

  7 omega  -61.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000    0.0000 49

  8 omega  -96.00  -55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000   90.0000 41

  9 omega  -70.00  -20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000   60.0000 50

 10 omega   59.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000 -180.0000 47

 11 omega   83.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000  -30.0000 28

 12 omega   81.00  106.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   71.0000   17.0064 25

 13 omega   81.00  107.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   68.0000    2.0823 26

 14 omega  134.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   71.0000   17.0064 44

 15 omega   85.00  110.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   55.0000   57.6344 25

 16 omega  126.00  176.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   69.0000    6.2369 50

 17 omega   78.00  135.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   22.0000   82.6574 57

 18 omega  139.00  165.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   46.0000  101.2887 26

 19 omega   81.00  106.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   75.0000  146.9811 25

 20 omega   81.00  107.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   69.0000    6.2369 26

 21 omega   82.00  124.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   65.0000  122.3920 42

 22 omega   52.00  103.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -73.0000  -73.7539 51

 23 omega   29.00   61.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -60.0000 32

 24 omega   85.00  116.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 31

 25 omega  102.00  147.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -150.0000 45

 26 omega  110.00  136.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -90.0000 26

 27 omega  137.00  177.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 40

 28 omega   70.00  106.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -150.0000 36

 29 omega   83.00  108.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 25

 30 omega   37.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 51

 31 omega   81.00  106.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   68.0000   91.0009 25

 32 omega  145.00  176.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   58.0000   92.3312 31

 33 omega  127.00  177.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   47.0000  110.7239 50

 34 omega   79.00  104.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 25

 35 omega   80.00  106.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   75.0000   56.3285 26

 36 omega   41.00   99.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000    0.0000 58

 37 omega  132.00  164.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 32

 38 omega  138.00  167.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 29

 39 omega   48.00   73.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -180.0000 25

 40 omega   86.00  115.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -180.0000 29

 41 omega   83.00  121.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 38

 42 omega  138.00  164.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 26

 43 omega  116.00  146.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   30.0000 30

 44 omega   62.00  102.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 40

 45 omega   79.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 26

 46 omega  130.00  170.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 40

 47 omega   82.00  107.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 25

 48 omega   49.00   82.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 33

 49 omega   87.00  113.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   50.0000  140.0680 26

 50 omega   38.00   94.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 56

 51 omega   85.00  110.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   60.0000 25

 52 omega   35.00   95.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -90.0000 60

 53 omega  115.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   48.0000   72.8552 63

 54 omega   83.00  109.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 26

 55 omega   83.00  109.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   58.0000   92.3312 26

 56 omega   30.00   55.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -150.0000 25

 57 omega   79.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 26

 58 omega   97.00  134.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -90.0000 37

 59 omega   79.00  110.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 31

 60 omega   83.00  118.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  150.0000 35

 61 omega   67.00   94.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 27

 62 omega  116.00  141.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   30.0000 25

 63 omega   86.00  112.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   48.0000   72.8552 26

 64 omega  115.00  159.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -180.0000 44

 65 omega  137.00  163.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   90.0000 26

 66 omega   29.00   71.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  120.0000 42

 67 omega   84.00  109.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 25

 68 omega   80.00  107.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 27

 69 omega   36.00   85.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -120.0000 49

 70 omega   35.00   66.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 31

 71 omega   80.00  109.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 29

 72 omega   44.00   69.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   90.0000 25

 73 omega   86.00  112.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 26

 74 omega  134.00  163.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 29

 75 omega   85.00  111.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   90.0000 26

 76 omega   37.00   91.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 54

 77 omega   87.00  112.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 25

 78 omega   85.00  111.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  150.0000 26

 79 omega  150.00  176.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  150.0000 26

 80 omega   85.00  111.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 26

 81 omega   83.00  109.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 26

 82 omega   84.00  109.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   60.0000 25

 83 omega  139.00  164.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   60.0000 25

 84 omega   44.00   70.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   90.0000 26

 85 omega  117.00  142.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   90.0000 25

 86 omega   40.00   80.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   30.0000 40

 87 omega  153.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   30.0000 25

 88 omega   35.00   60.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 25

 89 omega  121.00  146.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   30.0000 25

 90 omega   84.00  116.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  120.0000 32

 91 omega   74.00   99.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 25

 92 omega   36.00   63.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -60.0000 27

 93 omega  114.00  146.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -60.0000 32
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0515839000
_diffrn_orient_matrix_UB_12      -0.0510159000
_diffrn_orient_matrix_UB_13      0.0647169000
_diffrn_orient_matrix_UB_21      0.0548084000
_diffrn_orient_matrix_UB_22      0.0308514000
_diffrn_orient_matrix_UB_23      0.1162554000
_diffrn_orient_matrix_UB_31      -0.1149870000
_diffrn_orient_matrix_UB_32      -0.0080940000
_diffrn_orient_matrix_UB_33      0.0358350000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            62195
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.985
_diffrn_reflns_theta_min         3.452
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44751
_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            'light yellow'
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_description       prism
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.364
_refine_diff_density_min         -1.370
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         6337
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0304
_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^)+(0.0467P)^2^+0.7394P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0760
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5668
_reflns_number_total             6337
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic5b02246_si_003.cif
_cod_data_source_block           Compound_p25
_cod_original_cell_volume        3358.64(7)
_cod_database_code               4346856
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 94.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O43-H43
 1 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1), C6(H6), C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C41(H41A,H41B)
3.c Aromatic/amide H refined with riding coordinates:
 N12(H12), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C23(H23),
 C24(H24), C27(H27), C28(H28), C30(H30), C31(H31), C35(H35), C36(H36)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C26(H26A,H26B,H26C), C34(H34A,H34B,H34C), C42(H42A,H42B,
 H42C), C44(H44A,H44B,H44C)
;