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_4089064
_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, C12 H26 B10 N3 O'
_chemical_formula_sum            'C37 H48 B10 N3 O P'
_chemical_formula_weight         689.85
_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                70.5087(18)
_cell_angle_beta                 88.8007(16)
_cell_angle_gamma                79.0086(19)
_cell_formula_units_Z            4
_cell_length_a                   11.3975(3)
_cell_length_b                   18.5885(5)
_cell_length_c                   19.6960(3)
_cell_measurement_reflns_used    20252
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0900
_cell_measurement_theta_min      3.9330
_cell_volume                     3857.43(17)
_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  -70.00   33.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   77.0000 -150.0000 103

  2 omega -113.00  -15.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -77.0000    0.0000 98

  3 omega  -43.00   29.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000  -30.0000 72

  4 omega  -99.00  -13.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -77.0000   90.0000 86

  5 omega   92.00  121.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4354  178.0000    0.0000 29

  6 omega   40.00   68.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   90.0000 28

  7 omega  142.00  174.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  -90.0000 32

  8 omega   62.00   92.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -60.0000 30

  9 omega   65.00   90.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000    0.0000 25

 10 omega   39.00   69.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  120.0000 30

 11 omega   44.00   70.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000   90.0000 26

 12 omega   44.00   97.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -120.0000 53

 13 omega   63.00   91.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 28

 14 omega   86.00  120.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000 -120.0000 34

 15 omega   38.00   99.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000 -120.0000 61

 16 omega   43.00  111.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000 -180.0000 68

 17 omega  104.00  130.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000    0.0000 26

 18 omega   97.00  176.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  -60.0000 79

 19 omega   40.00  117.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000    0.0000 77

 20 omega  107.00  132.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000  150.0000 25

 21 omega  144.00  173.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000  150.0000 29

 22 omega   85.00  127.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  -90.0000 42

 23 omega  123.00  174.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000 -150.0000 51

 24 omega  133.00  158.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -30.0000 25

 25 omega   84.00  140.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000   90.0000 56

 26 omega   86.00  127.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -30.0000 41

 27 omega   60.00   87.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000    0.0000 27

 28 omega   84.00  109.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000    0.0000 25

 29 omega   55.00   80.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  -30.0000 25

 30 omega   96.00  121.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  -30.0000 25

 31 omega   95.00  121.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   90.0000 26

 32 omega   38.00   68.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   60.0000 30

 33 omega   63.00   99.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   60.0000 36

 34 omega  153.00  178.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000 -120.0000 25

 35 omega   70.00   95.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000 -150.0000 25

 36 omega   40.00   65.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -120.0000 25

 37 omega   85.00  125.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -120.0000 40

 38 omega   50.00   76.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  -90.0000 26

 39 omega   98.00  130.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  -90.0000 32

 40 omega   46.00  121.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  150.0000 75

 41 omega   90.00  171.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -150.0000 81

 42 omega   91.00  142.00   1.0000   13.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000    0.0000 51
;
_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      0.1372980000
_diffrn_orient_matrix_UB_12      -0.0251545000
_diffrn_orient_matrix_UB_13      0.0056689000
_diffrn_orient_matrix_UB_21      -0.0121669000
_diffrn_orient_matrix_UB_22      -0.0860270000
_diffrn_orient_matrix_UB_23      0.0265773000
_diffrn_orient_matrix_UB_31      -0.0009320000
_diffrn_orient_matrix_UB_32      0.0009158000
_diffrn_orient_matrix_UB_33      -0.0784890000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            43371
_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         72.496
_diffrn_reflns_theta_min         3.955
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.879
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77272
_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    1.188
_exptl_crystal_description       prism
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_platon_squeeze_details
;
;
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     939
_refine_ls_number_reflns         15267
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0681P)^2^+0.4438P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1123
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13377
_reflns_number_total             15267
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om6b00678_si_003.cif
_cod_data_source_block           Ph3PCH2Ph_10
_cod_original_cell_volume        3857.45(15)
_cod_database_code               4089064
_chemical_oxdiff_formula         'P B10 C36 N4 O'
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     75.12
_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:
 C13(H13A,H13B), C13A(H13C,H13D), C3A(H3AC,H3AD), C4A(H4AA,H4AB), C6A(H6AA,
 H6AB), C3(H3D,H3E), C4(H4B,H4C), C6(H6B,H6C)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31),
  C33(H33), C34(H34), C35(H35), C36(H36), C37(H37), C15A(H15A), C16A(H16A),
 C17A(H17A), C18A(H18A), C19A(H19A), C21A(H21A), C22A(H22A), C23A(H23A),
 C24A(H24A), C25A(H25A), C27A(H27A), C28A(H28A), C29A(H29A), C30A(H30A),
 C31A(H31A), C33A(H33A), C34A(H34A), C35A(H35A), C36A(H36A), C37A(H37A),
 N1A(H1A), C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A), C12A(H12A), N1(H1),
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
2.c X=CH2 refined with riding coordinates:
 N3A(H3AA,H3AB), N3(H3B,H3C)
2.d Idealised Me refined as rotating group:
 C5A(H5AA,H5AB,H5AC), C5(H5B,H5C,H5D)
2.e Boron cage BH refined with riding coordinates:
 B1A(H1AA), B3A(H3A), B4A(H4A), B5A(H5A), B6A(H6A), B7A(H7A), B8A(H8AA),
 B9A(H9AA), B10A(H10B), B1(H1B), B3(H3), B4(H4), B5(H5), B6(H6), B7(H7),
 B8(H8B), B9(H9B), B10(H10C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'