Mechanism of generation of closo-decaborato amidrazones. Intramolecular non-covalent B‒H⋯π(Ph) interaction determines stabilization of the configuration around the amidrazone CN bond
Burianova, Valeria K.; Bolotin, Dmitrii S.; Mikherdov, Alexander S.; Novikov, Alexander S.; Mokolokolo, Pennie Petrus; Roodt, Andreas; Boyarskiy, Vadim P.; Dar’in, Dmitry; Krasavin, Mikhail; Suslonov, Vitalii V.; Zhdanov, Andrey P.; Zhizhin, Konstantin Yu.; Kuznetsov, Nikolay T.; New Journal of Chemistry 42 (2018) 8693–; doi:10.1039/C8NJ01018H

data_7057271
_publ_section_title
;
 Mechanism of generation of closo-decaborato amidrazones. Intramolecular
 non-covalent B--H&#x22EF;\p(Ph) interaction determines stabilization of
 the configuration around the amidrazone C&#xE001;N bond
;
_journal_issue                   11
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8693
_journal_paper_doi               10.1039/C8NJ01018H
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C16 H26 B10 N3, C25 H22 P, C2 H3 N'
_chemical_formula_sum            'C43 H51 B10 N4 P'
_chemical_formula_weight         762.94
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-03-03
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-07-21 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                83.712(4)
_cell_angle_beta                 80.129(5)
_cell_angle_gamma                71.574(4)
_cell_formula_units_Z            2
_cell_length_a                   12.8766(7)
_cell_length_b                   12.9464(4)
_cell_length_c                   13.7638(7)
_cell_measurement_reflns_used    12337
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.6930
_cell_measurement_theta_min      3.2150
_cell_volume                     2140.88(18)
_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  -85.00   -3.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  -57.0000  120.0000 82

  2 omega  -78.00  -52.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  178.0000   30.0000 26

  3 omega  -34.00   46.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803   57.0000    0.0000 80

  4 omega  -89.00   21.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  -19.0000 -180.0000 110

  5 omega  -83.00  -10.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  130.0000   14.0000 73

  6 omega   39.00   84.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178 -130.0000  -57.0000 45

  7 omega   10.00   36.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178 -130.0000  -57.0000 26

  8 omega  -93.00    7.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  -77.0000   30.0000 100

  9 omega  -30.00    7.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  -77.0000 -180.0000 37

 10 omega  -42.00   45.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  -57.0000  150.0000 87

 11 omega  -49.00   35.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  -38.0000 -120.0000 84

 12 omega    3.00   74.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178   57.0000  -30.0000 71
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0144573000
_diffrn_orient_matrix_UB_12      0.0087819000
_diffrn_orient_matrix_UB_13      -0.0483575000
_diffrn_orient_matrix_UB_21      -0.0560675000
_diffrn_orient_matrix_UB_22      0.0064511000
_diffrn_orient_matrix_UB_23      0.0200794000
_diffrn_orient_matrix_UB_31      -0.0095396000
_diffrn_orient_matrix_UB_32      0.0568142000
_diffrn_orient_matrix_UB_33      0.0020357000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35574
_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         27.499
_diffrn_reflns_theta_min         2.682
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87164
_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    1.184
_exptl_crystal_description       prism
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         9820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0453P)^2^+0.8956P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1008
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8461
_reflns_number_total             9820
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj01018h2.cif
_cod_data_source_block           phch3pph3_3g
_cod_depositor_comments
'Adding full bibliography for 7057270--7057276.cif.'
_cod_original_cell_volume        2140.87(19)
_cod_database_code               7057271
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'P B10 N3 C16'
_reflns_odcompleteness_completeness 99.91
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1A(H1AA,H1AB)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C3A(H3AA), C4A(H4A), C5A(H5A), C6A(H6AA),
 C7A(H7AA), C9A(H9AA), C10A(H10B), C11A(H11A), C12A(H12A), C13A(H13A),
 C15A(H15A), C16A(H16A), C17A(H17A), C18A(H18A), C19A(H19A), C21A(H21A),
 C22A(H22A), C23A(H23A), C24A(H24A), C25A(H25A)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C2S(H2SA,H2SB,H2SC)
2.d Boron cage BH refined with riding coordinates:
 B1(H1A), B3(H3), B4(H4), B5(H5), B6(H6A), B7(H7A), B8(H8A), B9(H9A), B10(H10A)
;
_shelx_res_checksum              99860
_olex2_submission_special_instructions 'No special instructions were received'