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_7057273
_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         'C25 H22 P, C5 H20 B10 N3 O, C2 H3 N'
_chemical_formula_sum            'C32 H45 B10 N4 O P'
_chemical_formula_weight         640.79
_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
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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                73.017(6)
_cell_angle_beta                 85.201(4)
_cell_angle_gamma                69.039(5)
_cell_formula_units_Z            2
_cell_length_a                   9.9313(4)
_cell_length_b                   13.3634(11)
_cell_length_c                   15.4752(10)
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.5250
_cell_measurement_theta_min      3.2070
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_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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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   18.00   44.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   38.0000   90.0000 26

  2 omega  -89.00   51.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241    0.0000   90.0000 140

  3 omega  -23.00   53.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000  -60.0000 76

  4 omega   18.00   77.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616 -119.0000 -126.0000 59

  5 omega    4.00   65.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000   30.0000 61

  6 omega   39.00   65.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000   90.0000 26

  7 omega   23.00   82.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   57.0000  120.0000 59

  8 omega  -28.00   47.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   77.0000 -180.0000 75

  9 omega   35.00   63.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  178.0000 -150.0000 28

 10 omega   69.00   95.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  178.0000 -150.0000 26

 11 omega   -7.00   92.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000   60.0000 99

 12 omega   -7.00   93.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000  -60.0000 100

 13 omega   -7.00   57.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000 -150.0000 64
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
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_diffrn_orient_matrix_UB_11      0.0170526000
_diffrn_orient_matrix_UB_12      -0.0538359000
_diffrn_orient_matrix_UB_13      -0.0058881000
_diffrn_orient_matrix_UB_21      0.0133727000
_diffrn_orient_matrix_UB_22      -0.0242725000
_diffrn_orient_matrix_UB_23      0.0471865000
_diffrn_orient_matrix_UB_31      -0.0733695000
_diffrn_orient_matrix_UB_32      0.0046654000
_diffrn_orient_matrix_UB_33      0.0060658000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_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            31230
_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         27.498
_diffrn_reflns_theta_min         2.753
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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             676
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.485
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_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         8408
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0532P)^2^+0.8423P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1125
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7169
_reflns_number_total             8408
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj01018h2.cif
_cod_data_source_block           phch2pph3_3b
_cod_depositor_comments
'Adding full bibliography for 7057270--7057276.cif.'
_cod_original_cell_volume        1833.7(2)
_cod_database_code               7057273
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'B10 N3 C25 P'
_reflns_odcompleteness_completeness 99.90
_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:
 C1A(H1AA,H1AB), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A), C9A(H9A), C10A(H10A),
 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), N1(H1), N2(H2), N3(H3)
2.c Idealised Me refined as rotating group:
 C3(H3B,H3C,H3D), C5(H5B,H5C,H5D), C2S(H2SA,H2SB,H2SC)
2.d Boron cage BH refined with riding coordinates:
 B1(H1A), B3(H3E), B4(H4), B5(H5), B6(H6), B7(H7), B8(H8), B9(H9), B10(H10)
;
_shelx_res_checksum              91671
_olex2_submission_special_instructions 'No special instructions were received'