#------------------------------------------------------------------------------
#$Date: 2019-11-03 13:33:15 +0200 (Sun, 03 Nov 2019) $
#$Revision: 221533 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/84/4128414.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_4128414
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         'C28 H26 B2'
_chemical_formula_sum            'C28 H26 B2'
_chemical_formula_weight         384.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 98.997(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3844(7)
_cell_length_b                   8.6036(4)
_cell_length_c                   12.5024(8)
_cell_measurement_reflns_used    20370
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.94
_cell_measurement_theta_min      3.3
_cell_volume                     1103.26(12)
_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_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_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  0.0287
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19516
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.619
_diffrn_reflns_theta_min         3.300
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0477
_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)+(0.0653P)²+0.3536P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1282
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2469
_reflns_number_total             2812
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b01998_si_002.cif
_cod_data_source_block           wa2395
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4128414
_shelx_shelxl_version_number     2016/6
_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   0.982
_shelx_estimated_absorpt_t_max   0.984
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
_atom_site_refinement_flags_occupancy
B1 B 0.02203(13) 0.11535(14) 0.59144(10) 0.0217(2) Uani 1 1 d . . .
C1 C 0.09883(11) 0.13102(13) 0.49353(9) 0.0212(2) Uani 1 1 d . . .
C2 C 0.08142(11) 0.01754(13) 0.40938(9) 0.0210(2) Uani 1 1 d . . .
C3 C 0.16326(12) 0.02345(14) 0.32962(9) 0.0252(3) Uani 1 1 d . . .
H3 H 0.154026 -0.053387 0.274377 0.030 Uiso 1 1 calc R U .
C4 C 0.25755(12) 0.13906(15) 0.32949(10) 0.0282(3) Uani 1 1 d . . .
H4 H 0.311626 0.140556 0.274838 0.034 Uiso 1 1 calc R U .
C5 C 0.27160(12) 0.25156(15) 0.40971(10) 0.0281(3) Uani 1 1 d . . .
H5 H 0.334155 0.332052 0.409334 0.034 Uiso 1 1 calc R U .
C6 C 0.19376(11) 0.24656(14) 0.49111(9) 0.0247(2) Uani 1 1 d . . .
H6 H 0.205343 0.323409 0.546343 0.030 Uiso 1 1 calc R U .
C11 C 0.05315(11) 0.22572(14) 0.69240(9) 0.0239(2) Uani 1 1 d . . .
C12 C 0.09041(12) 0.16145(14) 0.79612(10) 0.0269(3) Uani 1 1 d . . .
H12 H 0.092960 0.051619 0.804005 0.032 Uiso 1 1 calc R U .
C13 C 0.12380(13) 0.25469(15) 0.88797(10) 0.0289(3) Uani 1 1 d . . .
C14 C 0.11554(12) 0.41576(15) 0.87568(10) 0.0288(3) Uani 1 1 d . . .
H14 H 0.136225 0.480186 0.937703 0.035 Uiso 1 1 calc R U .
C15 C 0.07773(11) 0.48450(14) 0.77473(10) 0.0260(3) Uani 1 1 d . . .
C16 C 0.04847(11) 0.38840(14) 0.68423(9) 0.0248(2) Uani 1 1 d . . .
H16 H 0.024633 0.434553 0.614934 0.030 Uiso 1 1 calc R U .
C17 C 0.16551(19) 0.18221(19) 0.99791(12) 0.0456(4) Uani 1 1 d . . .
H17A H 0.112281 0.089884 1.005164 0.068 Uiso 1 1 calc R U .
H17B H 0.153775 0.257471 1.054437 0.068 Uiso 1 1 calc R U .
H17C H 0.257535 0.152245 1.005501 0.068 Uiso 1 1 calc R U .
C18 C 0.06746(14) 0.65884(15) 0.76340(12) 0.0349(3) Uani 1 1 d . . .
H18A H 0.031110 0.702000 0.824806 0.052 Uiso 0.60(2) 1 calc R U P
H18B H 0.010306 0.684961 0.695788 0.052 Uiso 0.60(2) 1 calc R U P
H18C H 0.154294 0.702796 0.762247 0.052 Uiso 0.60(2) 1 calc R U P
H18D H 0.099364 0.691172 0.697088 0.052 Uiso 0.40(2) 1 calc R U P
H18E H 0.120167 0.708211 0.826106 0.052 Uiso 0.40(2) 1 calc R U P
H18F H -0.023821 0.690375 0.759647 0.052 Uiso 0.40(2) 1 calc R U P
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 119.29(9) 3_556 .
C2 B1 C11 120.02(10) 3_556 .
C1 B1 C11 120.61(10) . .
C6 C1 C2 118.52(10) . .
C6 C1 B1 121.50(10) . .
C2 C1 B1 119.73(10) . .
C3 C2 C1 118.47(10) . .
C3 C2 B1 120.68(10) . 3_556
C1 C2 B1 120.79(9) . 3_556
C4 C3 C2 121.83(11) . .
C4 C3 H3 119.1 . .
C2 C3 H3 119.1 . .
C5 C4 C3 119.45(11) . .
C5 C4 H4 120.3 . .
C3 C4 H4 120.3 . .
C4 C5 C6 119.93(11) . .
C4 C5 H5 120.0 . .
C6 C5 H5 120.0 . .
C5 C6 C1 121.76(11) . .
C5 C6 H6 119.1 . .
C1 C6 H6 119.1 . .
C16 C11 C12 117.41(11) . .
C16 C11 B1 122.92(10) . .
C12 C11 B1 119.66(11) . .
C13 C12 C11 121.88(12) . .
C13 C12 H12 119.1 . .
C11 C12 H12 119.1 . .
C14 C13 C12 118.42(11) . .
C14 C13 C17 120.95(12) . .
C12 C13 C17 120.62(12) . .
C15 C14 C13 121.66(11) . .
C15 C14 H14 119.2 . .
C13 C14 H14 119.2 . .
C14 C15 C16 118.53(11) . .
C14 C15 C18 120.84(11) . .
C16 C15 C18 120.63(12) . .
C15 C16 C11 122.07(11) . .
C15 C16 H16 119.0 . .
C11 C16 H16 119.0 . .
C13 C17 H17A 109.5 . .
C13 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C13 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C15 C18 H18A 109.5 . .
C15 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C15 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C15 C18 H18D 109.5 . .
H18A C18 H18D 141.1 . .
H18B C18 H18D 56.3 . .
H18C C18 H18D 56.3 . .
C15 C18 H18E 109.5 . .
H18A C18 H18E 56.3 . .
H18B C18 H18E 141.1 . .
H18C C18 H18E 56.3 . .
H18D C18 H18E 109.5 . .
C15 C18 H18F 109.5 . .
H18A C18 H18F 56.3 . .
H18B C18 H18F 56.3 . .
H18C C18 H18F 141.1 . .
H18D C18 H18F 109.5 . .
H18E C18 H18F 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 1.5678(17) 3_556
B1 C1 1.5678(16) .
B1 C11 1.5722(16) .
C1 C6 1.4037(16) .
C1 C2 1.4259(15) .
C2 C3 1.4087(15) .
C3 C4 1.3959(17) .
C3 H3 0.9500 .
C4 C5 1.3851(18) .
C4 H4 0.9500 .
C5 C6 1.3957(16) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C11 C16 1.4036(17) .
C11 C12 1.4071(16) .
C12 C13 1.3993(16) .
C12 H12 0.9500 .
C13 C14 1.3955(18) .
C13 C17 1.5098(18) .
C14 C15 1.3935(18) .
C14 H14 0.9500 .
C15 C16 1.3959(16) .
C15 C18 1.5089(18) .
C16 H16 0.9500 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C18 H18D 0.9800 .
C18 H18E 0.9800 .
C18 H18F 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 -179.06(10) 3_556 .
C11 B1 C1 C6 -2.28(17) . .
C2 B1 C1 C2 -4.94(17) 3_556 .
C11 B1 C1 C2 171.84(10) . .
C6 C1 C2 C3 2.09(16) . .
B1 C1 C2 C3 -172.21(10) . .
C6 C1 C2 B1 179.31(10) . 3_556
B1 C1 C2 B1 5.02(18) . 3_556
C1 C2 C3 C4 -1.74(18) . .
B1 C2 C3 C4 -178.96(11) 3_556 .
C2 C3 C4 C5 -0.03(19) . .
C3 C4 C5 C6 1.43(19) . .
C4 C5 C6 C1 -1.04(19) . .
C2 C1 C6 C5 -0.75(17) . .
B1 C1 C6 C5 173.43(11) . .
C2 B1 C11 C16 -127.15(12) 3_556 .
C1 B1 C11 C16 56.09(16) . .
C2 B1 C11 C12 54.32(15) 3_556 .
C1 B1 C11 C12 -122.44(12) . .
C16 C11 C12 C13 -1.03(18) . .
B1 C11 C12 C13 177.59(11) . .
C11 C12 C13 C14 2.04(19) . .
C11 C12 C13 C17 -178.99(13) . .
C12 C13 C14 C15 -1.30(19) . .
C17 C13 C14 C15 179.74(13) . .
C13 C14 C15 C16 -0.42(18) . .
C13 C14 C15 C18 179.07(12) . .
C14 C15 C16 C11 1.48(18) . .
C18 C15 C16 C11 -178.01(11) . .
C12 C11 C16 C15 -0.77(17) . .
B1 C11 C16 C15 -179.34(11) . .
