A highly efficient antioxidant based on boron and a Schiff base bridged phenolic diphenylamine: synthesis, crystal structure and thermal and antioxidant properties
Wang, Shengpei; Yu, Shasha; Feng, Jianxiang; Liu, Shenggao; Acta Crystallographica Section C 75 (2019) –; doi:10.1107/S2053229619011331

data_2021746
_publ_section_title
;
 A highly efficient antioxidant based on boron and a Schiff base bridged
 phenolic diphenylamine: synthesis, crystal structure and thermal and
 antioxidant properties
;
_journal_coeditor_code           JX3038
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229619011331
_journal_volume                  75
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C39 H41 B N2 O'
_chemical_formula_moiety         'C39 H41 B N2 O'
_chemical_formula_sum            'C39 H41 B N2 O'
_chemical_formula_weight         564.55
_chemical_name_common
;
(<i>E</i>)-4-({3,5-Di-<i>tert</i>-butyl-2-[(diphenylboranyl)oxy]\
benzylidene}amino)-<i>N</i>-phenylaniline
;
_chemical_name_systematic
;
{2-[(4-Anilinophenyl)iminomethyl-\k<i>N</i>]-4,6-di-<i>tert</i>-\
butylphenolato-\k<i>O</i>}diphenylboron
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 96.0950(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.6730(5)
_cell_length_b                   10.0539(4)
_cell_length_c                   15.0271(7)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.2
_cell_volume                     1603.37(12)
_computing_cell_refinement
;
SAINT (Bruker, 2010)
;
_computing_data_collection
;
APEX2 (Bruker, 2010)
;
_computing_data_reduction
;
SAINT (Bruker, 2010)
;
_computing_molecular_graphics
;
SHELXTL (Bruker, 2010)
;
_computing_publication_material
;
SHELXTL (Bruker, 2010)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23747
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.442
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.153
_refine_ls_abs_structure_details
;
Flack (1983), 3116 Friedel pairs
The experimental value of the Flack parameter is unreliable, as
it has a large s.u.
The following item in the CIF and the Table is the refined Flack
parameter, 0.1(4).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_coef       0.080(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2016 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         6249
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0513P)^2^+0.1760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1095
_reflns_number_gt                5477
_reflns_number_total             6249
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jx3038sup1.cif
_cod_data_source_block           I
_cod_database_code               2021746
_cod_database_fobs_code          2021746
_shelx_estimated_absorpt_t_min   0.986
_shelx_estimated_absorpt_t_max   0.991
_shelx_hkl_checksum              35201
_shelx_res_checksum              5239