Nucleophilicity of Oximes Based upon Addition to a Nitriliumcloso-Decaborate Cluster
Bolotin, Dmitrii S.; Burianova, Valeria K.; Novikov, Alexander S.; Demakova, Marina Ya.; Pretorius, Carla; Mokolokolo, Pennie Petrus; Roodt, Andreas; Bokach, Nadezhda A.; Suslonov, Vitaliy V.; Zhdanov, Andrey P.; Zhizhin, Konstantin Yu.; Kuznetsov, Nikolay T.; Kukushkin, Vadim Yu.; Organometallics 35 (2016) 3612–; doi:10.1021/acs.organomet.6b00678

data_4089062
_publ_section_title
;
 Nucleophilicity of Oximes Based upon Addition to a
 Nitriliumcloso-Decaborate Cluster
;
_journal_issue                   20
_journal_name_full               Organometallics
_journal_page_first              3612
_journal_paper_doi               10.1021/acs.organomet.6b00678
_journal_volume                  35
_journal_year                    2016
_chemical_formula_moiety         'C25 H22 P, C11 H24 B10 N3 O, 0.5(C2 H3 N)'
_chemical_formula_sum            'C37 H47.5 B10 N3.5 O P'
_chemical_formula_weight         696.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-10
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                76.584(3)
_cell_angle_beta                 89.932(3)
_cell_angle_gamma                78.878(3)
_cell_formula_units_Z            4
_cell_length_a                   11.3716(2)
_cell_length_b                   17.9770(7)
_cell_length_c                   19.6497(8)
_cell_measurement_reflns_used    21394
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0470
_cell_measurement_theta_min      3.0030
_cell_volume                     3829.9(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -46.00   30.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000    0.0000 76

  2 omega  -32.00   29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000  150.0000 61

  3 omega   61.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4354  178.0000  150.0000 66

  4 omega  114.00  151.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   99.0000  139.0000 37

  5 omega  152.00  177.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000   60.0000 25

  6 omega  106.00  132.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000   60.0000 26

  7 omega   90.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4354  178.0000  -30.0000 39

  8 omega   81.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4354  178.0000 -120.0000 26

  9 omega   93.00  173.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -120.0000 80

 10 omega  128.00  167.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000   30.0000 39

 11 omega   88.00  164.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000    0.0000 76

 12 omega   86.00  112.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  -30.0000 26

 13 omega   92.00  121.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  -90.0000 29

 14 omega   62.00   92.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   30.0000 30

 15 omega   80.00  112.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  120.0000 32

 16 omega   64.00  130.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  150.0000 66

 17 omega   67.00   92.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000   30.0000 25

 18 omega   47.00   88.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -30.0000 41

 19 omega   66.00   97.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -120.0000 31

 20 omega   60.00   97.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000 -180.0000 37

 21 omega   40.00   68.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 28

 22 omega   40.00   77.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  -30.0000 37

 23 omega   43.00  121.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   30.0000 78

 24 omega   36.00   90.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 54

 25 omega   41.00   90.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   90.0000 49

 26 omega   40.00   96.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000    0.0000 56

 27 omega   33.00  109.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  120.0000 76

 28 omega   35.00   62.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000    0.0000 27

 29 omega -121.00   -8.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -19.0000 -180.0000 113

 30 omega  115.00  140.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   99.0000  139.0000 25

 31 omega    1.00   26.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   89.0000 -169.5698 25

 32 omega    3.00   28.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   85.0000   32.8427 25

 33 omega -105.00  -61.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -38.0000   90.0000 44

 34 omega -115.00  -58.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -57.0000    0.0000 57

 35 omega  -50.00  -13.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -57.0000    0.0000 37

 36 omega  -57.00  -18.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -38.0000   90.0000 39

 37 omega  -48.00   32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000  -90.0000 80

 38 omega   11.00   36.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   84.0000  -95.4873 25

 39 omega   21.00   46.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000 -124.3338 25

 40 omega   22.00   49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000  -58.6373 27

 41 omega   21.00   46.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000  -13.6322 25

 42 omega   20.00   45.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000  173.7965 25

 43 omega   20.00   45.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000   48.4046 25

 44 omega   29.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000   77.5915 26

 45 omega   29.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000  103.3287 26

 46 omega   29.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000  136.5802 26

 47 omega   34.00   60.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000 -145.5116 26

 48 omega   33.00   59.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  -22.0181 26

 49 omega   37.00   62.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000   34.7142 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0410171000
_diffrn_orient_matrix_UB_12      0.0877949000
_diffrn_orient_matrix_UB_13      -0.0039931000
_diffrn_orient_matrix_UB_21      -0.0462178000
_diffrn_orient_matrix_UB_22      0.0130817000
_diffrn_orient_matrix_UB_23      -0.0763599000
_diffrn_orient_matrix_UB_31      -0.1236285000
_diffrn_orient_matrix_UB_32      -0.0141211000
_diffrn_orient_matrix_UB_33      0.0257544000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            45434
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.491
_diffrn_reflns_theta_min         3.031
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.894
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       prism
_exptl_crystal_F_000             1468
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.022
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     949
_refine_ls_number_reflns         15156
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0775P)^2^+2.4581P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1406
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13196
_reflns_number_total             15156
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om6b00678_si_003.cif
_cod_data_source_block           Ph3PCH2Ph_5_05MeCN
_cod_depositor_comments
;

2020-05-25
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C74 H95 B20 N7 O2 P2'
_cod_original_formula_weight         1392.70
_cod_original_formula_moiety     '2(C25 H22 P), 2(C11 H24 B10 N3 O), C2 H3 N'
_cod_original_formula_units_Z            2
_cod_database_code               4089062
_chemical_oxdiff_formula         'P B10 C36 N4 O'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups, All N(H) groups, All
  N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5A(H5AA,H5AB), C12(H12A,H12B), C5(H5A,H5B), C3(H3C,H3D), C3A(H3AC,H3AD),
 C12A(H12C,H12D)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C29(H29), C27(H27), C30(H30), C7A(H7AA), C8A(H8AB), C20(H20),
 C28(H28), N1A(H1AA), C26(H26), C7(H7), C10(H10), C11A(H11A), C10A(H10B),
 C16(H16), C22(H22), C17(H17), C8(H8), C24(H24), C11(H11), C18(H18), C21(H21),
 C33(H33), C9(H9), C36(H36), C35(H35), C14(H14), C9A(H9AA), C36A(H36A),
 C34A(H34A), C33A(H33A), C32A(H32A), C14A(H14A), C30A(H30A), C35A(H35A),
 C28A(H28A), C18A(H18A), C15A(H15A), C23A(H23A), C16A(H16A), C26A(H26A),
 C24A(H24A), C27A(H27A), C17A(H17A), C23(H23), C29A(H29A), C20A(H20A),
 C21A(H21A), C32(H32), C22A(H22A), C15(H15), C34(H34)
2.c X=CH2 refined with riding coordinates:
 N3A(H3AA,H3AB), N3(H3A,H3B)
2.d Idealised Me refined as rotating group:
 C4A(H4AB,H4AD,H4AC), C4(H4A,H4B,H4C), C2S(H2SA,H2SC,H2SB)
2.e Boron cage BH refined with riding coordinates:
 B8A(H8AA), B4(H4), B4A(H4AA), B7A(H7AB), B10A(H10C), B7(H7A), B5(H5),
 B5A(H5AC), B10(H10A), B8(H8A), B1A(H1AB), B6(H6), B6A(H6A), B3(H3), B9A(H9AB),
 B3A(H3AE), B9(H9A), B1(H1A)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'