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_4089060
_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, C10 H22 B10 N3 O, C2 H3 N'
_chemical_formula_sum            'C37 H47 B10 N4 O P'
_chemical_formula_weight         702.85
_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             2016-08-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                64.937(5)
_cell_angle_beta                 77.248(4)
_cell_angle_gamma                72.437(4)
_cell_formula_units_Z            2
_cell_length_a                   9.4705(4)
_cell_length_b                   14.2282(7)
_cell_length_c                   16.6636(8)
_cell_measurement_reflns_used    9256
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1090
_cell_measurement_theta_min      3.5830
_cell_volume                     1927.90(18)
_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 1.000
_diffrn_measurement_details
;
  1 omega  -34.00   29.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000  -90.0000 63

  2 omega  -42.00   30.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000   90.0000 72

  3 omega   79.00  130.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.4354  178.0000  -90.0000 51

  4 omega   95.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000 -150.0000 26

  5 omega  140.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000 -150.0000 37

  6 omega  149.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000  -30.0000 29

  7 omega  113.00  139.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000  -30.0000 26

  8 omega   95.00  145.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -90.0000 50

  9 omega  148.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000 -180.0000 30

 10 omega  119.00  144.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -150.0000 25

 11 omega   75.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000 -180.0000 33

 12 omega   75.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -49.0000 -148.1913 25

 13 omega   70.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -150.0000 38

 14 omega   59.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -113.0000 -169.0000 27

 15 omega   51.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -150.0000 51

 16 omega   54.00  101.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  -60.0000 47

 17 omega   84.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000    0.0000 25

 18 omega   81.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   30.0000 29

 19 omega   87.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   60.0000 34

 20 omega   84.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   60.0000 25

 21 omega   67.00  118.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  150.0000 51

 22 omega   61.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  120.0000 32

 23 omega   46.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   30.0000 31

 24 omega   43.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   60.0000 26

 25 omega   31.00   61.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   60.0000 30

 26 omega   31.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  150.0000 54

 27 omega   39.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  150.0000 47

 28 omega   44.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  150.0000 43

 29 omega   99.00  131.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000  150.0000 32

 30 omega  152.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000  150.0000 25

 31 omega  123.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000   90.0000 52

 32 omega  123.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000  120.0000 26

 33 omega   95.00  174.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   30.0000 79

 34 omega   87.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -60.0000 91

 35 omega   97.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000 -180.0000 79

 36 omega   90.00  143.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -180.0000 53

 37 omega   56.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  -30.0000 37

 38 omega   46.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  -30.0000 39

 39 omega   40.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   30.0000 50

 40 omega   37.00   62.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -90.0000 25

 41 omega   51.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -180.0000 36

 42 omega   44.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000 -180.0000 73

 43 omega   56.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.4354 -178.0000   30.0000 46

 44 omega  -82.00   38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   19.0000 -150.0000 120

 45 omega   76.00  119.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.4354  178.0000  120.0000 43

 46 omega -116.00  -17.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -38.0000  120.0000 99

 47 omega  -64.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -57.0000  -90.0000 49

 48 omega  -55.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -57.0000   30.0000 40
;
_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      -0.0556016000
_diffrn_orient_matrix_UB_12      0.0692104000
_diffrn_orient_matrix_UB_13      0.0561665000
_diffrn_orient_matrix_UB_21      -0.0216035000
_diffrn_orient_matrix_UB_22      -0.0996125000
_diffrn_orient_matrix_UB_23      0.0838277000
_diffrn_orient_matrix_UB_31      0.1609178000
_diffrn_orient_matrix_UB_32      -0.0203777000
_diffrn_orient_matrix_UB_33      0.0188843000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25279
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.499
_diffrn_reflns_theta_min         3.529
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.897
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88443
_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    1.211
_exptl_crystal_description       prism
_exptl_crystal_F_000             740
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     480
_refine_ls_number_reflns         7659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0421
_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^)+(0.0627P)^2^+0.6907P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6452
_reflns_number_total             7659
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om6b00678_si_003.cif
_cod_data_source_block           Ph3PCH2Ph_6_MeCN
_cod_original_cell_volume        1927.90(17)
_cod_database_code               4089060
_chemical_oxdiff_formula         'B12 N3 C10 H36'
_reflns_odcompleteness_completeness 97.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.49
_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:
 C11(H11A,H11B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C31(H31), C34(H34), N1(H1), C6(H6), C23(H23), C16(H16), C19(H19), C20(H20),
 C17(H17), C13(H13), C25(H25), C35(H35), C28(H28), C33(H33), C15(H15), C9(H9A),
 C29(H29), C32(H32), C14(H14), C21(H21), C27(H27), C22(H22), C10(H10), C26(H26),
  C8(H8A), C7(H7)
2.c X=CH2 refined with riding coordinates:
 N3(H3C,H3D)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C2S(H2SA,H2SB,H2SC)
2.e Boron cage BH refined with riding coordinates:
 B1(H1A), B9(H9), B4(H4), B5(H5), B8(H8), B3(H3), B6(H6A), B10(H10A), B7(H7A)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'