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_7057275
_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, C11 H25 B10 N4 O'
_chemical_formula_sum            'C36 H47 B10 N4 O P'
_chemical_formula_weight         690.84
_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 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_audit_update_record
;
2017-07-21 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                74.598(3)
_cell_angle_beta                 68.135(4)
_cell_angle_gamma                85.169(3)
_cell_formula_units_Z            2
_cell_length_a                   12.0810(5)
_cell_length_b                   13.0655(4)
_cell_length_c                   13.4841(7)
_cell_measurement_reflns_used    8567
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0370
_cell_measurement_theta_min      3.4730
_cell_volume                     1904.08(15)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -50.00   33.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000    0.0000 83

  2 omega  -44.00   29.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000  150.0000 73

  3 omega   56.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.4354  -99.0000   90.0000 26

  4 omega   55.00  106.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   30.0000 51

  5 omega  111.00  144.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   30.0000 33

  6 omega   91.00  121.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega   83.00  120.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   88.00  121.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   30.0000 33

  9 omega   73.00   99.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  -60.0000 26

 10 omega   69.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -90.0000 26

 11 omega  140.00  165.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000  -90.0000 25

 12 omega  127.00  164.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000  -90.0000 37

 13 omega  152.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 14 omega  111.00  137.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 15 omega   86.00  169.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -60.0000 83

 16 omega  104.00  153.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000 -120.0000 49

 17 omega  101.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       41.4354  178.0000  -30.0000 26

 18 omega   94.00  120.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000  120.0000 26

 19 omega  132.00  162.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000  120.0000 30

 20 omega   65.00  116.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 21 omega   84.00  128.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -120.0000 44

 22 omega   73.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 25

 23 omega   59.00   96.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   30.0000 37

 24 omega   51.00  106.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   90.0000 55

 25 omega   42.00   73.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000    0.0000 31

 26 omega   37.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000    0.0000 54

 27 omega   41.00  133.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000  -90.0000 92

 28 omega   67.00  109.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000 -180.0000 42

 29 omega   88.00  121.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000 -180.0000 33

 30 omega   61.00  140.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -180.0000 79

 31 omega   59.00  100.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -180.0000 41

 32 omega   49.00   79.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000 -180.0000 30

 33 omega   40.00   65.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000 -150.0000 25

 34 omega   45.00   72.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  -60.0000 27

 35 omega   37.00   82.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  -30.0000 45

 36 omega   39.00  111.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   60.0000 72

 37 omega   43.00   97.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  120.0000 54

 38 omega -115.00  -14.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -57.0000 -150.0000 101

 39 omega -115.00  -38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  178.0000  -60.0000 77

 40 omega  -58.00  -13.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -57.0000   90.0000 45

 41 omega  -91.00  -64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -57.0000   90.0000 27

 42 omega -111.00  -18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -38.0000  -30.0000 93

 43 omega  -69.00   33.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   77.0000 -120.0000 102

 44 omega    5.00   32.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   90.0000  -23.8483 27

 45 omega    5.00   30.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   89.0000  163.5919 25

 46 omega   11.00   36.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   84.0000   60.2839 25

 47 omega   13.00   38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   79.0000 -114.1881 25

 48 omega   20.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000   69.7880 25

 49 omega   21.00   46.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000  -37.4739 25

 50 omega   20.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000  -97.1398 25

 51 omega   31.00   57.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   74.0000 -179.2064 26

 52 omega   34.00   60.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000   36.4626 26

 53 omega   34.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000   83.4484 32

 54 omega   33.00   58.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  -84.2765 25
;
_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      0.0004195000
_diffrn_orient_matrix_UB_12      0.0255628000
_diffrn_orient_matrix_UB_13      -0.1184460000
_diffrn_orient_matrix_UB_21      -0.1363629000
_diffrn_orient_matrix_UB_22      -0.0167330000
_diffrn_orient_matrix_UB_23      0.0465090000
_diffrn_orient_matrix_UB_31      -0.0170252000
_diffrn_orient_matrix_UB_32      0.1184425000
_diffrn_orient_matrix_UB_33      -0.0011522000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25940
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.497
_diffrn_reflns_theta_min         3.509
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.899
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72643
_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    1.205
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.205
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         7538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0700P)^2^+0.7151P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1309
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6061
_reflns_number_total             7538
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj01018h2.cif
_cod_data_source_block           phch2pph3_3c
_cod_depositor_comments
'Adding full bibliography for 7057270--7057276.cif.'
_cod_database_code               7057275
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'B10 P C36 N3 O H40'
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     75.12
_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:
 C1A(H1AA,H1AB), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C19A(H19A), C7A(H7AA), C9A(H9AA), C15A(H15A), C3A(H3AA), C17A(H17A),
 C25A(H25A), C23A(H23A), C13A(H13A), C16A(H16A), C24A(H24A), C18A(H18A),
 C6A(H6AA), C22A(H22A), C4A(H4AA), C12A(H12A), C21A(H21A), C5A(H5A), C10A(H10B),
  C11A(H11D), N1(H1), N2(H2), C7(H7), C6(H6), C10(H10), C9(H9)
2.c X=CH2 refined with riding coordinates:
 N4(H4A,H4B)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C11(H11A,H11B,H11C)
2.e Boron cage BH refined with riding coordinates:
 B5(H5), B7(H7A), B9(H9A), B6(H6A), B3(H3), B1(H1A), B10(H10A), B8(H8), B4(H4)
;
_shelx_res_checksum              89151
_olex2_submission_special_instructions 'No special instructions were received'