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_4089061
_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, C8 H25 B10 N4 O2'
_chemical_formula_sum            'C33 H47 B10 N4 O2 P'
_chemical_formula_weight         670.81
_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                75.084(3)
_cell_angle_beta                 85.019(3)
_cell_angle_gamma                84.536(3)
_cell_formula_units_Z            2
_cell_length_a                   9.9583(3)
_cell_length_b                   12.4732(4)
_cell_length_c                   15.1134(5)
_cell_measurement_reflns_used    11868
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1190
_cell_measurement_theta_min      3.6570
_cell_volume                     1801.97(10)
_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 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega  -50.00   27.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000  -60.0000 77

  2 omega  -69.00   29.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   57.0000 -180.0000 98

  3 omega -110.00  -24.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -57.0000   30.0000 86

  4 omega -129.00  -35.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354 -178.0000 -150.0000 94

  5 omega   83.00  129.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4354 -178.0000  -30.0000 46

  6 omega   78.00  104.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000 -120.0000 26

  7 omega  108.00  143.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -120.0000 35

  8 omega  110.00  141.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -180.0000 31

  9 omega  109.00  159.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   17.0000 -113.3844 50

 10 omega  123.00  176.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000 -180.0000 53

 11 omega  115.00  168.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000  -30.0000 53

 12 omega  115.00  144.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000    0.0000 29

 13 omega   91.00  117.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   30.0000 26

 14 omega   84.00  109.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   90.0000 25

 15 omega   83.00  109.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  120.0000 26

 16 omega   94.00  140.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -64.0000  147.8955 46

 17 omega  132.00  162.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000  120.0000 30

 18 omega  116.00  143.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  120.0000 27

 19 omega   87.00  151.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   60.0000 64

 20 omega  101.00  127.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000  -60.0000 26

 21 omega  144.00  170.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000  -90.0000 26

 22 omega  151.00  177.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000  -60.0000 26

 23 omega  147.00  175.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000 -180.0000 28

 24 omega  122.00  165.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000 -150.0000 43

 25 omega   66.00   97.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   17.0000 -113.3844 31

 26 omega   58.00   86.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -180.0000 28

 27 omega   61.00  102.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000 -180.0000 41

 28 omega   53.00   81.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -90.0000 28

 29 omega   83.00  109.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -67.0000 -121.0000 26

 30 omega   71.00   97.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  -60.0000 26

 31 omega   81.00  121.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  -60.0000 40

 32 omega   88.00  145.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -89.0000   11.2387 57

 33 omega   86.00  121.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  120.0000 35

 34 omega   60.00   86.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 26

 35 omega   46.00   72.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000    0.0000 26

 36 omega   47.00   88.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -31.0000  -48.5465 41

 37 omega   63.00  103.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000  -30.0000 40

 38 omega   43.00   83.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   90.0000 40

 39 omega   48.00   87.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  150.0000 39

 40 omega   41.00  102.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -52.0000   88.6044 61

 41 omega   45.00  117.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   60.0000 72

 42 omega   44.00   95.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  150.0000 51

 43 omega   39.00   75.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   30.0000 36

 44 omega   39.00   87.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   90.0000 48

 45 omega   31.00   66.00   1.0000   14.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   90.0000 35
;
_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      0.0432469000
_diffrn_orient_matrix_UB_12      0.0855523000
_diffrn_orient_matrix_UB_13      0.0474411000
_diffrn_orient_matrix_UB_21      0.1274031000
_diffrn_orient_matrix_UB_22      0.0169317000
_diffrn_orient_matrix_UB_23      -0.0660528000
_diffrn_orient_matrix_UB_31      -0.0784326000
_diffrn_orient_matrix_UB_32      0.0939435000
_diffrn_orient_matrix_UB_33      -0.0675361000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20514
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.499
_diffrn_reflns_theta_min         3.678
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.954
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86324
_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    1.236
_exptl_crystal_description       prism
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.283
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         7134
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.291
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0795
_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^)+(0.0071P)^2^+3.6350P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1638
_refine_ls_wR_factor_ref         0.1642
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6957
_reflns_number_total             7134
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om6b00678_si_003.cif
_cod_data_source_block           Ph3PCH2Ph_4
_cod_original_cell_volume        1801.96(11)
_cod_database_code               4089061
_chemical_oxdiff_formula         'P B10 C36 N4 O'
_reflns_odcompleteness_completeness 93.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_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. Restrained distances
 B10_$1-H10_$1
 1.1 with sigma of 0.002
3. Uiso/Uaniso restraints and constraints
Uanis(P1) = Uanis(P1A)
Uanis(C14A) = Uanis(C26)
Uanis(C24) = Uanis(C12A)
Uanis(C33) = Uanis(C28A)
Uanis(C29A) = Uanis(C32)
4. Others
 Sof(P1A)=Sof(C9A)=Sof(H9AB)=Sof(H9AA)=Sof(C10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=
 Sof(H12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=
 Sof(C16A)=Sof(H17A)=Sof(H20A)=Sof(C26A)=Sof(H26A)=Sof(C21A)=Sof(C22A)=
 Sof(H22A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=Sof(H24A)=Sof(C25A)=Sof(H25A)=
 Sof(C27A)=Sof(C28A)=Sof(H28A)=Sof(C29A)=Sof(H29A)=Sof(C30A)=Sof(H30A)=
 Sof(C31A)=Sof(H31A)=Sof(C32A)=Sof(H32A)=Sof(C1V)=Sof(H1V)=1-FVAR(1)
 Sof(P1)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C14)=Sof(H14)=Sof(C13)=Sof(H13)=
 Sof(C12)=Sof(H12)=Sof(C11)=Sof(H11)=Sof(C10)=Sof(C15)=Sof(H15)=Sof(C22)=
 Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26)=
 Sof(C27)=Sof(H27)=Sof(C28)=Sof(C29)=Sof(H29)=Sof(C30)=Sof(H30)=Sof(C31)=
 Sof(H31)=Sof(C32)=Sof(H32)=Sof(C33)=Sof(H33)=Sof(C34)=Sof(C39)=Sof(H39)=
 Sof(H17B)=Sof(H20B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C9A(H9AB,H9AA), C3(H3C,H3D), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,
 H7B), C8(H8A,H8B)
5.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C12(H12), C11(H11), C15(H15), C23(H23), C24(H24),
 C25(H25), C26(H26), C27(H27), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33),
  C39(H39), C11A(H11A), C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A),
 C17A(H17A), C17A(H17B), C18A(H18A), C19A(H19A), C20A(H20A), C20A(H20B),
 C26A(H26A), C22A(H22A), C23A(H23A), C24A(H24A), C25A(H25A), C28A(H28A),
 C29A(H29A), C30A(H30A), C31A(H31A), C32A(H32A), C1V(H1V), N1(H1)
5.c Fitted hexagon refined as free rotating group:
 C14(C13,C12,C11,C10,C15), C26A(C21A,C22A,C23A,C24A,C25A)
5.d X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
5.e Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
5.f Boron cage BH refined with riding coordinates:
 B1(H1A), B3(H3), B4(H4), B5(H5), B6(H6), B7(H7), B8(H8), B9(H9), B10(H10)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'