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_4089063
_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, C9 H20 B10 N3 O, C2 H3 N'
_chemical_formula_sum            'C36 H45 B10 N4 O P'
_chemical_formula_weight         688.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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                90
_cell_angle_beta                 104.362(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1998(6)
_cell_length_b                   12.8001(4)
_cell_length_c                   18.7831(7)
_cell_measurement_reflns_used    8125
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.8270
_cell_measurement_theta_min      3.2480
_cell_volume                     3773.1(2)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -91.00  -42.00   1.0000   73.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241 -178.0000    0.0000 49

  2 omega  -90.00  -36.00   1.0000   73.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241 -178.0000 -120.0000 54

  3 omega  -34.00   47.00   1.0000   73.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   19.0000  -30.0000 81

  4 omega   -2.00   88.00   1.0000   73.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178   38.0000 -120.0000 90

  5 omega   21.00   46.00   1.0000   73.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   57.0000   60.0000 25

  6 omega   61.00   96.00   1.0000   73.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  178.0000  -60.0000 35

  7 omega   49.00   75.00   1.0000   73.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178   57.0000    0.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0076501000
_diffrn_orient_matrix_UB_12      0.0458617000
_diffrn_orient_matrix_UB_13      0.0185417000
_diffrn_orient_matrix_UB_21      0.0444768000
_diffrn_orient_matrix_UB_22      0.0054086000
_diffrn_orient_matrix_UB_23      0.0155452000
_diffrn_orient_matrix_UB_31      0.0035799000
_diffrn_orient_matrix_UB_32      0.0305725000
_diffrn_orient_matrix_UB_33      -0.0305297000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26745
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.747
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97052
_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    1.213
_exptl_crystal_description       prism
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         8660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0516P)^2^+2.0624P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1115
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7196
_reflns_number_total             8660
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om6b00678_si_003.cif
_cod_data_source_block           Ph3PCH2Ph_3_MeCN
_cod_database_code               4089063
_chemical_oxdiff_formula         'B10 N3 P O C33'
_reflns_odcompleteness_completeness 99.87
_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 Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C28(H28), C24(H24), C32(H32),
 C26(H26), C12(H12), C30(H30), C13(H13), C14(H14), C15(H15), C25(H25), C16(H16),
  C27(H27), C18(H18), C31(H31), C19(H19), C33(H33), C20(H20), C21(H21),
 C22(H22), C34(H34)
2.c X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
2.d Idealised Me refined as rotating group:
 C3(H3C,H3D,H3E), C2S(H2SA,H2SB,H2SC)
2.e Boron cage BH refined with riding coordinates:
 B1(H1A), B3(H3), B4(H4), B5(H5A), B6(H6A), B7(H7A), B8(H8A), B9(H9A), B10(H10)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'