Bifunctional reactivity of amidoximes observed upon nucleophilic addition to metal-activated nitriles.
Bolotin, Dmitrii S.; Demakova, Marina Ya; Novikov, Alexander S.; Avdontceva, Margarita S.; Kuznetsov, Maxim L.; Bokach, Nadezhda A.; Kukushkin, Vadim Yu; Inorganic chemistry 54 (2015) 4039–4046; doi:10.1021/acs.inorgchem.5b00253

data_4346084
_publ_section_title
;
 Bifunctional reactivity of amidoximes observed upon nucleophilic addition
 to metal-activated nitriles.
;
_journal_issue                   8
_journal_name_full               'Inorganic chemistry'
_journal_page_first              4039
_journal_page_last               4046
_journal_paper_doi               10.1021/acs.inorgchem.5b00253
_journal_volume                  54
_journal_year                    2015
_chemical_formula_moiety         'C21 H17 Br Cl2 N4 O Pt, C H Cl3'
_chemical_formula_sum            'C22 H18 Br Cl5 N4 O Pt'
_chemical_formula_weight         806.65
_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   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.9538(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.99961(17)
_cell_length_b                   11.26583(16)
_cell_length_c                   23.3589(4)
_cell_measurement_reflns_used    26822
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7410
_cell_measurement_theta_min      3.7670
_cell_volume                     2627.98(7)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9969
_diffrn_measurement_details
;
  1 omega    3.00   28.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0000   88.0000 -121.5745 25

  2 omega -129.00  -44.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  178.0000  -60.0000 85

  3 omega -110.00  -16.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000 -180.0000 94

  4 omega  -63.00   30.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   57.0000  150.0000 93

  5 omega -113.00  -11.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000   90.0000 102

  6 omega -110.00  -11.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000    0.0000 99

  7 omega    1.00   81.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000 -150.0000 80

  8 omega   80.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   77.0000  150.0000 30

  9 omega   57.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000   30.0000 47

 10 omega    8.00   33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   77.0000  150.0000 25

 11 omega    6.00   33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   89.0000  -29.4603 27

 12 omega   17.00   42.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   82.0000  -73.1236 25

 13 omega   17.00   42.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   81.0000  164.0316 25

 14 omega   18.00   43.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   80.0000   73.7575 25

 15 omega   22.00   47.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000   13.8773 25

 16 omega   22.00   47.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000 -139.1088 25

 17 omega   22.00   47.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000 -176.2941 25

 18 omega   23.00   48.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000 -109.0135 25

 19 omega   26.00   52.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   77.0000 -130.0468 26

 20 omega   31.00   63.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   74.0000  -62.9027 32

 21 omega   31.00   58.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   76.0000  102.1767 27

 22 omega   31.00   58.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   75.0000   64.1885 27

 23 omega   36.00   67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   71.0000 -137.3696 31

 24 omega   34.00   60.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000  131.0308 26

 25 omega   38.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000  152.5176 27

 26 omega   38.00   64.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000    8.0195 26

 27 omega   39.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   75.0000   80.9111 26

 28 omega   39.00   66.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   72.0000  -43.9556 27

 29 omega  107.00  134.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   75.0000   80.9111 27

 30 omega   38.00   64.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000  -22.5721 26

 31 omega   47.00   72.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   65.0000 -170.0748 25

 32 omega   48.00   75.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   69.0000  157.4782 27

 33 omega   47.00   76.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   72.0000 -145.8001 29

 34 omega   51.00   76.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   77.0000   18.7050 25

 35 omega   58.00  123.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   69.0000   44.0856 65

 36 omega   52.00  106.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   70.0000 -109.1011 54

 37 omega   55.00   82.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   59.0000  -49.4888 27

 38 omega   56.00   84.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   70.0000   76.1703 28

 39 omega   56.00   82.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   68.0000   -3.2558 26

 40 omega   55.00   81.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   72.0000  -49.0477 26

 41 omega   58.00   85.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       92.0000   77.0000 -172.5509 27

 42 omega   69.00  145.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   71.0000  122.2016 76

 43 omega   76.00  101.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   72.0000 -178.0876 25

 44 omega   81.00  120.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   68.0000 -152.8305 39

 45 omega   84.00  164.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -120.0000 80

 46 omega  141.00  168.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -110.4383 27

 47 omega   80.00  134.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -110.4383 54

 48 omega   43.00  101.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -120.0000 58

 49 omega  120.00  169.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -60.0000 49

 50 omega   79.00  118.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -60.0000 39

 51 omega   83.00  147.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 64

 52 omega   36.00  115.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 79

 53 omega   96.00  124.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  150.0000 28

 54 omega   39.00   80.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  150.0000 41

 55 omega   97.00  177.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -180.0000 80

 56 omega   32.00   96.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  150.0000 64

 57 omega   79.00  105.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 26

 58 omega  117.00  169.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 52

 59 omega  119.00  144.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -90.0000 25

 60 omega   79.00  128.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 49

 61 omega  150.00  178.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 28

 62 omega   59.00   99.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -90.0000 40

 63 omega   86.00  141.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 55

 64 omega   79.00  177.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 98

 65 omega   40.00   74.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   30.0000 34

 66 omega   87.00  115.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 28

 67 omega   35.00   70.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 35

 68 omega   35.00   72.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 37

 69 omega   50.00  109.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 59

 70 omega   79.00  171.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -90.0000 92

 71 omega  127.00  152.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 25

 72 omega   49.00   80.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -150.0000 31

 73 omega   83.00  109.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 26

 74 omega  150.00  177.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 27

 75 omega   80.00  172.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 92

 76 omega   80.00  132.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 52

 77 omega   36.00  114.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 78

 78 omega   85.00  125.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 40

 79 omega   84.00  143.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 59

 80 omega   97.00  144.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -69.0000   96.8334 47

 81 omega  143.00  170.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 27

 82 omega   39.00   71.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -69.0000   96.8334 32

 83 omega   85.00  118.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 33

 84 omega  115.00  140.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -150.0000 25

 85 omega  134.00  170.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 36

 86 omega   79.00  149.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -19.0000  104.7928 70

 87 omega   80.00  118.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 38

 88 omega  118.00  176.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 58

 89 omega   86.00  111.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 25

 90 omega   78.00  105.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 27

 91 omega   92.00  117.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -115.0000   36.1575 25

 92 omega  109.00  136.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   30.0000 27

 93 omega   79.00  105.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 26

 94 omega   36.00   85.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -115.0000   36.1575 49
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0297399000
_diffrn_orient_matrix_UB_12      0.1329350000
_diffrn_orient_matrix_UB_13      0.0094835000
_diffrn_orient_matrix_UB_21      -0.1508476000
_diffrn_orient_matrix_UB_22      0.0276487000
_diffrn_orient_matrix_UB_23      -0.0073571000
_diffrn_orient_matrix_UB_31      -0.0133032000
_diffrn_orient_matrix_UB_32      -0.0163787000
_diffrn_orient_matrix_UB_33      0.0649065000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0865
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            58136
_diffrn_reflns_theta_full        69.97
_diffrn_reflns_theta_max         69.97
_diffrn_reflns_theta_min         3.79
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    16.649
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47544
_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            colorless
_exptl_crystal_density_diffrn    2.039
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.2304
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.0299
_refine_diff_density_max         5.654
_refine_diff_density_min         -1.114
_refine_diff_density_rms         0.247
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4967
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0682
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0899P)^2^+33.8474P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1693
_refine_ls_wR_factor_ref         0.1716
_reflns_number_gt                4701
_reflns_number_total             4967
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic5b00253_si_002.cif
_cod_data_source_block           16
_cod_database_code               4346084
_chemical_oxdiff_formula         'Pt Cl2 C21 H17 n2 Br'
_reflns_odcompleteness_completeness 94.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_olex2_submission_special_instructions 'No special instructions were received'