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_7057274
_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         '1(C25 H22 P), C10 H22 B10 Br N4'
_chemical_formula_sum            'C35 H44 B10 Br N4 P'
_chemical_formula_weight         739.72
_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   mixed
_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                73.394(3)
_cell_angle_beta                 83.153(2)
_cell_angle_gamma                86.422(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4455(3)
_cell_length_b                   12.6195(4)
_cell_length_c                   16.4179(4)
_cell_measurement_reflns_used    11145
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7640
_cell_measurement_theta_min      3.6310
_cell_volume                     1861.15(10)
_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 0.998
_diffrn_measurement_details
;
  1 omega -128.00  -51.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  178.0000  -60.0000 77

  2 omega -113.00  -11.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000 -150.0000 102

  3 omega  -50.00   36.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000    0.0000 86

  4 omega -118.00  -89.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  178.0000   30.0000 29

  5 omega  105.00  130.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000    0.0000 25

  6 omega  -33.00   67.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -57.0000   90.0000 100

  7 omega   22.00   52.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   38.0000   60.0000 30

  8 omega   87.00  116.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   38.0000   60.0000 29

  9 omega   36.00   91.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 55

 10 omega   35.00   99.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 64

 11 omega   50.00   82.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 32

 12 omega   62.00   96.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 34

 13 omega   52.00   90.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000    0.0000 38

 14 omega   62.00  114.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 52

 15 omega   49.00  142.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  150.0000 93

 16 omega   89.00  115.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 26

 17 omega  110.00  177.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -180.0000 67

 18 omega   41.00   97.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   60.0000 56

 19 omega  117.00  174.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  120.0000 57

 20 omega   98.00  133.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -150.0000 35

 21 omega   51.00  115.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   30.0000 64

 22 omega   31.00  164.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  120.0000 133

 23 omega  -82.00  -15.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000   30.0000 67

 24 omega  -52.00  -12.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000  -30.0000 40

 25 omega -110.00  -77.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000  -30.0000 33

 26 omega -118.00  -42.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787 -178.0000 -180.0000 76

 27 omega    1.00   26.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   92.0000   45.0525 25

 28 omega    6.00   32.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   90.0000  179.6005 26

 29 omega   14.00   39.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   80.0000  -76.9306 25

 30 omega   17.00   42.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   81.0000   78.1782 25

 31 omega   17.00   44.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   81.0000   -8.4173 27

 32 omega   22.00   47.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000 -159.1109 25

 33 omega   23.00   48.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000  -62.4562 25

 34 omega   31.00   58.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   76.0000   27.4102 27

 35 omega   31.00   58.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   74.0000  119.0483 27

 36 omega   36.00   61.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000   51.7117 25

 37 omega   35.00   64.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000   84.4684 29

 38 omega   35.00   74.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000  -88.4743 39

 39 omega   36.00   64.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000  -28.3018 28

 40 omega  113.00  140.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000  129.6704 27

 41 omega   38.00   78.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000  129.6704 40

 42 omega   99.00  126.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   72.0000 -144.1834 27

 43 omega   44.00   73.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   76.0000 -124.9394 29

 44 omega   43.00   69.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   73.0000 -173.7698 26

 45 omega   43.00   69.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   72.0000 -144.1834 26

 46 omega   46.00   73.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   67.0000  -51.9231 27

 47 omega   50.00   80.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   51.0000   44.9995 30

 48 omega   47.00   73.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   76.0000  -54.0474 26

 49 omega   55.00   84.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   77.0000  -32.5213 29

 50 omega   58.00   86.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   69.0000   51.7550 28

 51 omega   57.00   84.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   68.0000   80.4121 27

 52 omega  102.00  127.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   77.0000  -32.5213 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      -0.1343878000
_diffrn_orient_matrix_UB_12      0.0629140000
_diffrn_orient_matrix_UB_13      0.0266470000
_diffrn_orient_matrix_UB_21      -0.0880190000
_diffrn_orient_matrix_UB_22      -0.1040296000
_diffrn_orient_matrix_UB_23      0.0156291000
_diffrn_orient_matrix_UB_31      0.0346652000
_diffrn_orient_matrix_UB_32      -0.0382429000
_diffrn_orient_matrix_UB_33      0.0935015000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22442
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.994
_diffrn_reflns_theta_min         2.825
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.145
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56169
_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    1.320
_exptl_crystal_description       plate
_exptl_crystal_F_000             764
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.837
_refine_diff_density_min         -0.872
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     534
_refine_ls_number_reflns         7061
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0389P)^2^+2.2864P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1197
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6232
_reflns_number_total             7061
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj01018h2.cif
_cod_data_source_block           phch2pph3_3e
_cod_depositor_comments
'Adding full bibliography for 7057270--7057276.cif.'
_cod_original_cell_volume        1861.16(10)
_cod_database_code               7057274
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'B10 Br C48 N4'
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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. Uiso/Uaniso restraints and constraints
Uanis(C8B) = Uanis(C8A)
Uanis(C9B) = Uanis(C9A)
Uanis(C10A) = Uanis(C10B)
Uanis(C11A) = Uanis(C11B)
Uanis(C12A) = Uanis(C12B)
Uanis(C13A) = Uanis(C13B)
Uanis(C4A) = Uanis(C18B)
Uanis(C6A) = Uanis(C16B)
Uanis(C7A) = Uanis(C15B)
Uanis(C2A) = Uanis(C14B)
Uanis(C7B) = Uanis(C19A)
Uanis(C14A) = Uanis(C2B)
Uanis(C15A) = Uanis(C3B)
Uanis(C16A) = Uanis(C4B)
Uanis(C17A) = Uanis(C5B)
Uanis(C18A) = Uanis(C6B)
Uanis(C25B) = Uanis(C25A)
Uanis(C22B) = Uanis(C22A)
Uanis(C23A) = Uanis(C23B)
Uanis(C24A) = Uanis(C24B)
Uanis(C5A) = Uanis(C17B)
Uanis(C20B) = Uanis(C20A)
3. Others
 Sof(P1B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(C2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=
 Sof(H4B)=Sof(C5B)=Sof(H5B)=Sof(C6B)=Sof(H6B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=
 Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12B)=
 Sof(C13B)=Sof(H13B)=Sof(C14B)=Sof(C19B)=Sof(H19B)=Sof(C18B)=Sof(H18B)=
 Sof(C17B)=Sof(H17B)=Sof(C16B)=Sof(H16B)=Sof(C15B)=Sof(H15B)=Sof(C20B)=
 Sof(C25B)=Sof(H25B)=Sof(C24B)=Sof(H24B)=Sof(C23B)=Sof(H23B)=Sof(C22B)=
 Sof(H22B)=Sof(C21B)=Sof(H21B)=1-FVAR(1)
 Sof(C21A)=Sof(H21A)=Sof(C13A)=Sof(H13A)=Sof(C17A)=Sof(H17A)=Sof(C25A)=
 Sof(H25A)=Sof(C11A)=Sof(H11A)=Sof(C15A)=Sof(H15A)=Sof(C19A)=Sof(H19A)=
 Sof(C23A)=Sof(H23A)=Sof(C12A)=Sof(H12A)=Sof(C14A)=Sof(C16A)=Sof(H16A)=
 Sof(C18A)=Sof(H18A)=Sof(C20A)=Sof(C22A)=Sof(H22A)=Sof(C24A)=Sof(H24A)=Sof(P1A)=
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4A)=
 Sof(C5A)=Sof(H5AA)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(C9A)=
 Sof(H9A)=Sof(C10A)=Sof(H10A)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C1B(H1BA,H1BB), C2(H2A,H2B), C1A(H1AA,H1AB)
4.b Aromatic/amide H refined with riding coordinates:
 C3B(H3B), C4B(H4B), C5B(H5B), C6B(H6B), C7B(H7B), C9B(H9B), C10B(H10B),
 C11B(H11B), C12B(H12B), C13B(H13B), C19B(H19B), C18B(H18B), C17B(H17B),
 C16B(H16B), C15B(H15B), C25B(H25B), C24B(H24B), C23B(H23B), C22B(H22B),
 C21B(H21B), C6(H6), C7(H7), C9(H9C), C10(H10), C21A(H21A), C13A(H13A),
 C17A(H17A), C25A(H25A), C11A(H11A), C15A(H15A), C19A(H19A), C23A(H23A),
 C12A(H12A), C16A(H16A), C18A(H18A), C22A(H22A), C24A(H24A), C3A(H3A), C4A(H4A),
  C5A(H5AA), C6A(H6A), C7A(H7A), C9A(H9A), C10A(H10A)
4.c Fitted hexagon refined as free rotating group:
 C8B(C9B,C10B,C11B,C12B,C13B), C14B(C19B,C18B,C17B,C16B,C15B), C20B(C25B,C24B,
 C23B,C22B,C21B)
4.d X=CH2 refined with riding coordinates:
 N4(H4C,H4D)
4.e Idealised Me refined as rotating group:
 C3(H3C,H3D,H3E)
4.f Boron cage BH refined with riding coordinates:
 B1(H1A), B3(H3), B4(H4), B5(H5), B6(H6C), B7(H7C), B8(H8), B9(H9), B10(H10C)
;
_shelx_res_checksum              65852
_olex2_submission_special_instructions 'No special instructions were received'