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#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/84/4128413.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4128413
loop_
_publ_author_name
'von Grotthuss, Esther'
'Prey, Sven E.'
'Bolte, Michael'
'Lerner, Hans-Wolfram'
'Wagner, Matthias'
_publ_section_title
;
 Dual Role of Doubly Reduced Arylboranes as Dihydrogen- and
 Hydride-Transfer Catalysts.
;
_journal_issue                   14
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6082
_journal_page_last               6091
_journal_paper_doi               10.1021/jacs.9b01998
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C16 H18 B2'
_chemical_formula_sum            'C16 H18 B2'
_chemical_formula_weight         231.92
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                76.716(9)
_cell_angle_beta                 74.826(9)
_cell_angle_gamma                84.882(9)
_cell_formula_units_Z            1
_cell_length_a                   5.1697(6)
_cell_length_b                   7.5135(9)
_cell_length_c                   9.1628(11)
_cell_measurement_reflns_used    5472
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.68
_cell_measurement_theta_min      4.02
_cell_volume                     334.15(7)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5472
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.337
_diffrn_reflns_theta_min         4.021
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_description       plate
_exptl_crystal_F_000             124
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1364
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0473
_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/[σ²(Fo²)+(0.0663P)²+0.1135P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1397
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1197
_reflns_number_total             1364
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b01998_si_002.cif
_cod_data_source_block           wa2362
_cod_database_code               4128413
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.997
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
B1 B 0.3666(3) 0.4107(2) 0.90736(18) 0.0264(4) Uani 1 1 d . .
C1 C 0.5949(3) 0.55230(19) 0.82388(15) 0.0265(3) Uani 1 1 d . .
C2 C 0.7256(3) 0.63256(18) 0.91079(15) 0.0257(3) Uani 1 1 d . .
C3 C 0.9348(3) 0.7525(2) 0.83030(17) 0.0313(4) Uani 1 1 d . .
H3 H 1.0239 0.8059 0.8874 0.038 Uiso 1 1 calc R U
C4 C 1.0153(3) 0.7952(2) 0.66921(18) 0.0355(4) Uani 1 1 d . .
H4 H 1.1577 0.8764 0.6176 0.043 Uiso 1 1 calc R U
C5 C 0.8864(3) 0.7187(2) 0.58510(17) 0.0360(4) Uani 1 1 d . .
H5 H 0.9391 0.7476 0.4752 0.043 Uiso 1 1 calc R U
C6 C 0.6795(3) 0.5993(2) 0.66186(17) 0.0326(4) Uani 1 1 d . .
H6 H 0.5925 0.5478 0.6026 0.039 Uiso 1 1 calc R U
C7 C 0.2577(3) 0.3006(2) 0.80951(17) 0.0312(4) Uani 1 1 d . .
H7A H 0.0784 0.2538 0.8678 0.037 Uiso 1 1 calc R U
H7B H 0.2401 0.3823 0.7109 0.037 Uiso 1 1 calc R U
C8 C 0.4536(4) 0.1398(2) 0.7761(2) 0.0462(5) Uani 1 1 d . .
H8A H 0.3864 0.0712 0.7154 0.069 Uiso 1 1 calc R U
H8B H 0.6301 0.1869 0.7176 0.069 Uiso 1 1 calc R U
H8C H 0.4689 0.0588 0.8741 0.069 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 B1 C1 118.62(12) 2_667 .
C2 B1 C7 121.26(13) 2_667 .
C1 B1 C7 119.79(12) . .
C6 C1 C2 118.12(13) . .
C6 C1 B1 120.87(12) . .
C2 C1 B1 120.99(12) . .
C3 C2 C1 118.54(12) . .
C3 C2 B1 121.14(12) . 2_667
C1 C2 B1 120.31(12) . 2_667
C4 C3 C2 121.89(13) . .
C4 C3 H3 119.1 . .
C2 C3 H3 119.1 . .
C5 C4 C3 119.47(14) . .
C5 C4 H4 120.3 . .
C3 C4 H4 120.3 . .
C4 C5 C6 119.78(14) . .
C4 C5 H5 120.1 . .
C6 C5 H5 120.1 . .
C5 C6 C1 122.19(13) . .
C5 C6 H6 118.9 . .
C1 C6 H6 118.9 . .
C8 C7 B1 109.32(12) . .
C8 C7 H7A 109.8 . .
B1 C7 H7A 109.8 . .
C8 C7 H7B 109.8 . .
B1 C7 H7B 109.8 . .
H7A C7 H7B 108.3 . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 C2 1.572(2) 2_667
B1 C1 1.577(2) .
B1 C7 1.5790(19) .
C1 C6 1.4024(19) .
C1 C2 1.4246(19) .
C2 C3 1.4059(19) .
C2 B1 1.572(2) 2_667
C3 C4 1.393(2) .
C3 H3 0.9500 .
C4 C5 1.382(2) .
C4 H4 0.9500 .
C5 C6 1.389(2) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C8 1.539(2) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C2 B1 C1 C6 -178.32(12) 2_667 .
C7 B1 C1 C6 8.1(2) . .
C2 B1 C1 C2 3.3(2) 2_667 .
C7 B1 C1 C2 -170.28(12) . .
C6 C1 C2 C3 -0.9(2) . .
B1 C1 C2 C3 177.57(12) . .
C6 C1 C2 B1 178.22(12) . 2_667
B1 C1 C2 B1 -3.3(2) . 2_667
C1 C2 C3 C4 0.4(2) . .
B1 C2 C3 C4 -178.67(13) 2_667 .
C2 C3 C4 C5 0.2(2) . .
C3 C4 C5 C6 -0.4(2) . .
C4 C5 C6 C1 -0.1(2) . .
C2 C1 C6 C5 0.7(2) . .
B1 C1 C6 C5 -177.74(13) . .
C2 B1 C7 C8 -93.56(16) 2_667 .
C1 B1 C7 C8 79.79(17) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 159652086
