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_4089065
_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                101.119(4)
_cell_angle_beta                 104.098(5)
_cell_angle_gamma                95.257(4)
_cell_formula_units_Z            2
_cell_length_a                   10.0492(6)
_cell_length_b                   11.5413(5)
_cell_length_c                   18.0725(9)
_cell_measurement_reflns_used    5079
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.7770
_cell_measurement_theta_min      3.1430
_cell_volume                     1973.50(19)
_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    '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_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega  -94.00   42.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803    0.0000 -180.0000 136

  2 omega  -93.00   -5.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  -77.0000 -180.0000 88

  3 omega   12.00   68.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178 -107.0000  -59.0000 56

  4 omega    6.00   62.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  -99.0000  120.0000 56

  5 omega  -22.00   28.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  -99.0000   30.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0027617000
_diffrn_orient_matrix_UB_12      -0.0001876000
_diffrn_orient_matrix_UB_13      0.0395692000
_diffrn_orient_matrix_UB_21      -0.0718625000
_diffrn_orient_matrix_UB_22      0.0041483000
_diffrn_orient_matrix_UB_23      -0.0077117000
_diffrn_orient_matrix_UB_31      -0.0154629000
_diffrn_orient_matrix_UB_32      -0.0631719000
_diffrn_orient_matrix_UB_33      -0.0098911000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15472
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.689
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99027
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_platon_squeeze_details
;
;
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         8939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0539P)^2^+0.6312P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1174
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7397
_reflns_number_total             8939
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om6b00678_si_003.cif
_cod_data_source_block           Ph3PCH2Ph_13
_cod_original_cell_volume        1973.50(17)
_cod_database_code               4089065
_chemical_oxdiff_formula         'C44 H41 N6 B10 P'
_reflns_odcompleteness_completeness 98.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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 Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C6(H6A,H6B)
2.c 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), N1(H1), C8(H8), C9(H9),
 C10(H10), C11(H11), C12(H12)
2.d X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
2.e Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
2.f Boron cage BH refined with riding coordinates:
 B1(H1A), B3(H3C), B4(H4), B5(H5), B6(H6), B7(H7), B8(H8A), B9(H9A), B10(H10A)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'