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_7057270
_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         'C11 H22 B10 F3 N4, C25 H22 P'
_chemical_formula_sum            'C36 H44 B10 F3 N4 P'
_chemical_formula_weight         728.82
_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                73.363(5)
_cell_angle_beta                 83.321(4)
_cell_angle_gamma                86.262(4)
_cell_formula_units_Z            2
_cell_length_a                   9.4224(4)
_cell_length_b                   12.6542(7)
_cell_length_c                   16.5596(10)
_cell_measurement_reflns_used    5701
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.6250
_cell_measurement_theta_min      3.6390
_cell_volume                     1877.90(18)
_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 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -50.00   35.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -180.0000 85

  2 omega -113.00  -12.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000   30.0000 101

  3 omega  -56.00   25.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   77.0000  -90.0000 81

  4 omega -102.00  -64.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000 -150.0000 38

  5 omega   42.00   82.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000  150.0000 40

  6 omega   64.00  128.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000   90.0000 64

  7 omega   38.00   97.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -90.0000 59

  8 omega   48.00   91.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 43

  9 omega   46.00   83.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 37

 10 omega   68.00  102.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 34

 11 omega  102.00  171.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -120.0000 69

 12 omega   60.00   85.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 25

 13 omega   37.00   82.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 45

 14 omega   35.00  115.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 80

 15 omega   47.00   96.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -60.0000 49

 16 omega   41.00  105.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  120.0000 64

 17 omega   57.00  110.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 53

 18 omega   40.00   66.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 26

 19 omega   67.00   96.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 29

 20 omega   45.00   70.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 25

 21 omega   38.00   86.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000    0.0000 48

 22 omega   86.00  112.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 26

 23 omega  138.00  164.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -120.0000 26

 24 omega   45.00  104.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   30.0000 59

 25 omega   29.00  171.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000 -120.0000 142
;
_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      -0.0040974000
_diffrn_orient_matrix_UB_12      0.0971755000
_diffrn_orient_matrix_UB_13      -0.0809756000
_diffrn_orient_matrix_UB_21      0.0148645000
_diffrn_orient_matrix_UB_22      -0.0817863000
_diffrn_orient_matrix_UB_23      -0.0540280000
_diffrn_orient_matrix_UB_31      -0.1639871000
_diffrn_orient_matrix_UB_32      -0.0055626000
_diffrn_orient_matrix_UB_33      0.0071385000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_unetI/netI     0.0894
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14212
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.493
_diffrn_reflns_theta_min         2.800
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.038
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52510
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         7420
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0690
_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^)+(0.1056P)^2^+0.4928P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1795
_refine_ls_wR_factor_ref         0.1959
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5741
_reflns_number_total             7420
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj01018h2.cif
_cod_data_source_block           phch2pph3_3f
_cod_depositor_comments
'Adding full bibliography for 7057270--7057276.cif.'
_cod_original_cell_volume        1877.89(18)
_cod_database_code               7057270
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'B10 C10 F3'
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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. Restrained distances
 H2-H7A_$1
 2 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C1B) = Uanis(C1A)
Uanis(C9B) = Uanis(C25A)
Uanis(C10B) = Uanis(C24A)
Uanis(C11B) = Uanis(C23A)
Uanis(C13B) = Uanis(C21A)
Uanis(C12B) = Uanis(C22A)
Uanis(C20A) = Uanis(C8B)
Uanis(P1A) = Uanis(P1B)
Uanis(F1) = Uanis(F4)
Uanis(F5) = Uanis(F2)
Uanis(F6) = Uanis(F3)
Uanis(C6A) = Uanis(C22B)
Uanis(C5A) = Uanis(C23B)
Uanis(C20B) = Uanis(C2A)
Uanis(C7A) = Uanis(C21B)
Uanis(C3A) = Uanis(C25B)
Uanis(C24B) = Uanis(C4A)
Uanis(C5B) = Uanis(C18A)
Uanis(C17A) = Uanis(C4B)
Uanis(C16A) = Uanis(C6B)
Uanis(C7B) = Uanis(C15A)
Uanis(C14A) = Uanis(C2B)
Uanis(C3B) = Uanis(C19A)
Uanis(C13A) = Uanis(C15B)
Uanis(C17B) = Uanis(C11A)
Uanis(C16B) = Uanis(C12A)
Uanis(C18B) = Uanis(C10A)
Uanis(C19B) = Uanis(C9A)
Uanis(C14B) = Uanis(C8A)
4. Others
 Sof(P1B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(C2B)=Sof(C7B)=Sof(H7B)=Sof(C6B)=
 Sof(H6B)=Sof(C5B)=Sof(H5B)=Sof(C4B)=Sof(H4BA)=Sof(C3B)=Sof(H3BA)=Sof(C8B)=
 Sof(C13B)=Sof(H13B)=Sof(C12B)=Sof(H12B)=Sof(C11B)=Sof(H11A)=Sof(C10B)=
 Sof(H10C)=Sof(C9B)=Sof(H9B)=Sof(C15B)=Sof(H15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=
 Sof(H17B)=Sof(C18B)=Sof(H18B)=Sof(C19B)=Sof(H19B)=Sof(C14B)=Sof(C20B)=
 Sof(C21B)=Sof(H21B)=Sof(C22B)=Sof(H22B)=Sof(C23B)=Sof(H23B)=Sof(C24B)=
 Sof(H24B)=Sof(C25B)=Sof(H25B)=1-FVAR(1)
 Sof(P1A)=Sof(C24A)=Sof(H24A)=Sof(C1A)=Sof(H1AB)=Sof(H1AC)=Sof(C22A)=Sof(H22A)=
 Sof(C2A)=Sof(C3A)=Sof(H3AB)=Sof(C4A)=Sof(H4AB)=Sof(C5A)=Sof(H5A)=Sof(C6A)=
 Sof(H6AA)=Sof(C7A)=Sof(H7AA)=Sof(C8A)=Sof(C23A)=Sof(H23A)=Sof(C9A)=Sof(H9AA)=
 Sof(C25A)=Sof(H25A)=Sof(C10A)=Sof(H10B)=Sof(C11A)=Sof(H11B)=Sof(C12A)=
 Sof(H12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=
 Sof(H16A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=
 Sof(C20A)=Sof(C21A)=Sof(H21A)=FVAR(1)
 Sof(F4)=Sof(F5)=Sof(F6)=1-FVAR(2)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1B(H1BA,H1BB), C1A(H1AB,H1AC)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C6(H6), C7(H7), C9(H9), C10(H10), C7B(H7B), C6B(H6B),
 C5B(H5B), C4B(H4BA), C3B(H3BA), C13B(H13B), C12B(H12B), C11B(H11A), C10B(H10C),
  C9B(H9B), C15B(H15B), C16B(H16B), C17B(H17B), C18B(H18B), C19B(H19B),
 C21B(H21B), C22B(H22B), C23B(H23B), C24B(H24B), C25B(H25B), C24A(H24A),
 C22A(H22A), C3A(H3AB), C4A(H4AB), C5A(H5A), C6A(H6AA), C7A(H7AA), C23A(H23A),
 C9A(H9AA), C25A(H25A), C10A(H10B), C11A(H11B), C12A(H12A), C13A(H13A),
 C15A(H15A), C16A(H16A), C17A(H17A), C18A(H18A), C19A(H19A), C21A(H21A)
5.c Fitted hexagon refined as free rotating group:
 C2B(C7B,C6B,C5B,C4B,C3B), C8B(C13B,C12B,C11B,C10B,C9B), C15B(C16B,C17B,C18B,
 C19B,C14B), C20B(C21B,C22B,C23B,C24B,C25B)
5.d X=CH2 refined with riding coordinates:
 N4(H4A,H4B)
5.e Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
5.f Boron cage BH refined with riding coordinates:
 B1(H1A), B3(H3), B4(H4), B5(H5), B6(H6A), B7(H7A), B8(H8), B9(H9A), B10(H10A)
;
_shelx_res_checksum              14689
_olex2_submission_special_instructions 'No special instructions were received'