#------------------------------------------------------------------------------
#$Date: 2019-09-19 03:06:53 +0300 (Thu, 19 Sep 2019) $
#$Revision: 218505 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/41/7124198.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_7124198
loop_
_publ_author_name
'Feng, Rui'
'Yang, Wenbang'
'Wang, Wenqing'
'Zhao, Yue'
'Tan, Gengwen'
'Zhang, Li'
'Wang, Xinping'
_publ_section_title
;
 Isolable diboryl radicals acting as highly efficient reaction
 intermediates under mild conditions
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC06514H
_journal_year                    2019
_chemical_formula_sum            'C10 H16 B O3'
_chemical_formula_weight         195.04
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-05-01 deposited with the CCDC.    2019-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.144(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0306(5)
_cell_length_b                   11.4395(9)
_cell_length_c                   15.2784(14)
_cell_measurement_reflns_used    3558
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.24
_cell_volume                     1040.62(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9178
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.694
_diffrn_reflns_theta_min         2.234
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6560
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2421
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0495
_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)+(0.0511P)²+0.4504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1219
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1905
_reflns_number_total             2421
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc06514h2.cif
_cod_data_source_block           5
_cod_database_code               7124198
_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   0.990
_shelx_estimated_absorpt_t_max   0.992
_exptl_absorpt_special_details   'SADABS (Bruker, 2014)'
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
O3 O 0.34068(17) 0.53772(8) 0.64160(7) 0.0217(3) Uani 1 1 d . .
O1 O 0.58511(18) 0.64665(9) 0.74045(7) 0.0233(3) Uani 1 1 d . .
O2 O 0.33260(18) 0.74350(8) 0.62514(7) 0.0229(3) Uani 1 1 d . .
C9 C 0.1697(2) 0.52182(12) 0.57025(10) 0.0177(3) Uani 1 1 d . .
C8 C 0.2115(2) 0.45128(12) 0.50084(10) 0.0194(3) Uani 1 1 d . .
H8 H 0.3528 0.4184 0.5016 0.023 Uiso 1 1 calc R U
C10 C -0.0406(2) 0.56986(12) 0.56985(10) 0.0195(3) Uani 1 1 d . .
H10 H -0.0680 0.6164 0.6169 0.023 Uiso 1 1 calc R U
C3 C 0.4408(2) 0.85588(12) 0.64759(10) 0.0205(3) Uani 1 1 d . .
C1 C 0.6603(3) 0.75386(12) 0.78797(10) 0.0216(4) Uani 1 1 d . .
C2 C 0.5211(3) 0.85876(12) 0.74775(10) 0.0215(3) Uani 1 1 d . .
H2A H 0.3902 0.8655 0.7770 0.026 Uiso 1 1 calc R U
H2B H 0.6101 0.9289 0.7615 0.026 Uiso 1 1 calc R U
C5 C 0.9102(3) 0.76627(14) 0.78538(12) 0.0292(4) Uani 1 1 d . .
H5A H 0.9872 0.6973 0.8097 0.044 Uiso 1 1 calc R U
H5B H 0.9677 0.8331 0.8197 0.044 Uiso 1 1 calc R U
H5C H 0.9336 0.7763 0.7251 0.044 Uiso 1 1 calc R U
C7 C 0.2593(3) 0.94795(13) 0.62255(12) 0.0281(4) Uani 1 1 d . .
H7A H 0.1918 0.9374 0.5618 0.042 Uiso 1 1 calc R U
H7B H 0.3252 1.0244 0.6300 0.042 Uiso 1 1 calc R U
H7C H 0.1467 0.9401 0.6601 0.042 Uiso 1 1 calc R U
C4 C 0.6228(3) 0.73492(15) 0.88273(11) 0.0318(4) Uani 1 1 d . .
H4A H 0.4656 0.7229 0.8837 0.048 Uiso 1 1 calc R U
H4B H 0.6733 0.8024 0.9176 0.048 Uiso 1 1 calc R U
H4C H 0.7056 0.6675 0.9068 0.048 Uiso 1 1 calc R U
C6 C 0.6246(3) 0.87076(15) 0.59122(11) 0.0289(4) Uani 1 1 d . .
H6A H 0.7263 0.8058 0.6008 0.043 Uiso 1 1 calc R U
H6B H 0.7051 0.9419 0.6075 0.043 Uiso 1 1 calc R U
H6C H 0.5588 0.8740 0.5298 0.043 Uiso 1 1 calc R U
B1 B 0.4192(3) 0.64699(14) 0.66926(11) 0.0184(4) Uani 1 1 d . .
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'
O O 0.0106 0.0060 '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
B1 O3 C9 122.37(11) . .
B1 O1 C1 121.86(11) . .
B1 O2 C3 118.63(11) . .
C10 C9 O3 121.22(13) . .
C10 C9 C8 120.43(13) . .
O3 C9 C8 118.27(13) . .
C10 C8 C9 119.50(14) 3_566 .
C10 C8 H8 120.2 3_566 .
C9 C8 H8 120.2 . .
C9 C10 C8 120.06(14) . 3_566
C9 C10 H10 120.0 . .
C8 C10 H10 120.0 3_566 .
O2 C3 C6 107.78(13) . .
O2 C3 C7 105.91(11) . .
C6 C3 C7 109.90(13) . .
O2 C3 C2 108.24(12) . .
C6 C3 C2 114.92(12) . .
C7 C3 C2 109.68(13) . .
O1 C1 C4 105.85(13) . .
O1 C1 C5 107.23(13) . .
C4 C1 C5 109.71(13) . .
O1 C1 C2 110.51(11) . .
C4 C1 C2 109.79(14) . .
C5 C1 C2 113.44(13) . .
C3 C2 C1 116.70(12) . .
C3 C2 H2A 108.1 . .
C1 C2 H2A 108.1 . .
C3 C2 H2B 108.1 . .
C1 C2 H2B 108.1 . .
H2A C2 H2B 107.3 . .
C1 C5 H5A 109.5 . .
C1 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C1 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C3 C7 H7A 109.5 . .
C3 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C3 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C1 C4 H4A 109.5 . .
C1 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C1 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C3 C6 H6A 109.5 . .
C3 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C3 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
O1 B1 O2 125.35(13) . .
O1 B1 O3 114.64(13) . .
O2 B1 O3 120.00(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 B1 1.3790(18) .
O3 C9 1.3884(15) .
O1 B1 1.3558(18) .
O1 C1 1.4602(16) .
O2 B1 1.3542(19) .
O2 C3 1.4577(16) .
C9 C10 1.381(2) .
C9 C8 1.387(2) .
C8 C10 1.3905(18) 3_566
C8 H8 0.9300 .
C10 C8 1.3905(18) 3_566
C10 H10 0.9300 .
C3 C6 1.518(2) .
C3 C7 1.523(2) .
C3 C2 1.530(2) .
C1 C4 1.516(2) .
C1 C5 1.521(2) .
C1 C2 1.536(2) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
