#------------------------------------------------------------------------------
#$Date: 2016-03-22 13:50:58 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178980 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/03/4120323.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_4120323
loop_
_publ_author_name
'Zaozao Qiu'
'Yangjian Quan'
'Zuowei Xie'
_publ_section_title
;
 Palladium-Catalyzed Selective Fluorination of o-Carboranes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12192
_journal_page_last               12195
_journal_paper_doi               10.1021/ja405808t
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C4 H12 B10 F4'
_chemical_formula_weight         244.24
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.945(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.735(3)
_cell_length_b                   7.9285(18)
_cell_length_c                   12.782(3)
_cell_measurement_reflns_used    561
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     1187.7(5)
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_sigmaI/netI    0.0621
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10884
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.6949
_exptl_absorpt_correction_T_min  0.5592
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0965
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1657P)²+1.6528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2955
_refine_ls_wR_factor_ref         0.3221
_reflns_number_gt                1483
_reflns_number_total             2107
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja405808t_si_001_1.cif
_cod_data_source_block           2b
_cod_database_code               4120323
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F 0.6442(3) 0.2137(4) 0.5175(2) 0.0686(10) Uani 1 1 d .
F2 F 0.8772(3) 0.1567(4) 0.6604(3) 0.0750(11) Uani 1 1 d .
F3 F 0.8673(3) 0.3978(4) 0.8640(2) 0.0707(11) Uani 1 1 d .
F4 F 0.6374(3) 0.2116(4) 0.7683(2) 0.0685(10) Uani 1 1 d .
C1 C 0.8134(4) 0.6409(5) 0.5919(3) 0.0364(10) Uani 1 1 d .
C2 C 0.6888(4) 0.6695(5) 0.6486(3) 0.0394(10) Uani 1 1 d .
C11 C 0.8661(5) 0.7860(6) 0.5342(4) 0.0569(14) Uani 1 1 d .
H11A H 0.8615 0.7634 0.4603 0.085 Uiso 1 1 calc R
H11B H 0.9446 0.7983 0.5579 0.085 Uiso 1 1 calc R
H11C H 0.8255 0.8881 0.5479 0.085 Uiso 1 1 calc R
C12 C 0.6317(5) 0.8406(7) 0.6404(6) 0.0703(17) Uani 1 1 d .
H12A H 0.5640 0.8327 0.5952 0.105 Uiso 1 1 calc R
H12B H 0.6832 0.9206 0.6121 0.105 Uiso 1 1 calc R
H12C H 0.6116 0.8768 0.7087 0.105 Uiso 1 1 calc R
B3 B 0.6924(4) 0.5528(6) 0.5361(4) 0.0431(12) Uani 1 1 d .
H3 H 0.6533 0.5935 0.4602 0.052 Uiso 1 1 calc R
B4 B 0.8217(5) 0.4403(7) 0.5448(4) 0.0435(12) Uani 1 1 d .
H4 H 0.8666 0.4047 0.4746 0.052 Uiso 1 1 calc R
B5 B 0.8972(4) 0.5033(7) 0.6615(4) 0.0413(12) Uani 1 1 d .
H5 H 0.9910 0.5094 0.6672 0.050 Uiso 1 1 calc R
B6 B 0.8122(4) 0.6527(6) 0.7247(4) 0.0395(12) Uani 1 1 d .
H6 H 0.8499 0.7578 0.7708 0.047 Uiso 1 1 calc R
B7 B 0.6101(4) 0.4908(7) 0.6414(4) 0.0452(13) Uani 1 1 d .
H7 H 0.5163 0.4889 0.6344 0.054 Uiso 1 1 calc R
B8 B 0.6929(5) 0.3399(6) 0.5763(4) 0.0441(12) Uani 1 1 d .
B9 B 0.8219(5) 0.3075(6) 0.6563(4) 0.0442(12) Uani 1 1 d .
B10 B 0.8174(5) 0.4409(7) 0.7698(4) 0.0432(12) Uani 1 1 d .
B11 B 0.6854(4) 0.5524(6) 0.7598(4) 0.0415(12) Uani 1 1 d .
H11 H 0.6410 0.5900 0.8298 0.050 Uiso 1 1 calc R
B12 B 0.6893(5) 0.3386(6) 0.7170(4) 0.0421(12) 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'
F F 0.0171 0.0103 '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
C11 C1 C2 119.6(4)
C11 C1 B5 120.4(4)
C2 C1 B5 110.8(3)
C11 C1 B6 117.9(3)
C2 C1 B6 60.6(3)
B5 C1 B6 62.9(3)
C11 C1 B4 120.3(4)
C2 C1 B4 110.2(3)
B5 C1 B4 62.7(3)
B6 C1 B4 114.0(3)
C11 C1 B3 117.3(4)
C2 C1 B3 60.8(3)
B5 C1 B3 113.9(3)
B6 C1 B3 113.0(3)
B4 C1 B3 62.1(3)
C12 C2 C1 118.9(4)
C12 C2 B7 120.5(4)
C1 C2 B7 110.4(3)
C12 C2 B11 121.2(4)
C1 C2 B11 110.2(3)
B7 C2 B11 63.4(3)
C12 C2 B6 117.9(4)
C1 C2 B6 60.3(3)
B7 C2 B6 114.3(3)
B11 C2 B6 62.4(3)
C12 C2 B3 117.1(4)
C1 C2 B3 60.3(3)
B7 C2 B3 62.5(3)
B11 C2 B3 114.2(3)
B6 C2 B3 112.3(3)
C1 B3 C2 58.9(3)
C1 B3 B4 59.0(3)
C2 B3 B4 106.2(3)
C1 B3 B8 106.3(3)
C2 B3 B8 105.7(4)
B4 B3 B8 60.4(3)
C1 B3 B7 105.7(3)
C2 B3 B7 58.1(3)
B4 B3 B7 108.3(4)
B8 B3 B7 60.3(3)
C1 B4 B3 59.0(3)
C1 B4 B5 58.2(3)
B3 B4 B5 107.7(3)
C1 B4 B9 105.5(3)
B3 B4 B9 108.5(4)
B5 B4 B9 60.6(3)
C1 B4 B8 105.9(4)
B3 B4 B8 59.9(3)
B5 B4 B8 109.4(4)
B9 B4 B8 61.1(3)
C1 B5 B4 59.0(3)
C1 B5 B6 58.8(3)
B4 B5 B6 107.7(3)
C1 B5 B10 105.9(3)
B4 B5 B10 108.4(4)
B6 B5 B10 60.0(3)
C1 B5 B9 105.5(3)
B4 B5 B9 59.8(3)
B6 B5 B9 108.0(3)
B10 B5 B9 60.5(3)
C1 B6 C2 59.1(3)
C1 B6 B11 106.2(3)
C2 B6 B11 58.6(3)
C1 B6 B5 58.2(3)
C2 B6 B5 105.9(3)
B11 B6 B5 108.4(3)
C1 B6 B10 105.7(3)
C2 B6 B10 105.8(3)
B11 B6 B10 60.4(3)
B5 B6 B10 60.3(3)
C2 B7 B3 59.4(3)
C2 B7 B8 106.3(3)
B3 B7 B8 59.8(3)
C2 B7 B12 105.7(3)
B3 B7 B12 108.2(4)
B8 B7 B12 60.9(3)
C2 B7 B11 58.5(3)
B3 B7 B11 107.7(4)
B8 B7 B11 108.9(4)
B12 B7 B11 60.1(3)
F1 B8 B3 123.2(4)
F1 B8 B4 122.9(4)
B3 B8 B4 59.6(3)
F1 B8 B7 122.1(4)
B3 B8 B7 59.9(3)
B4 B8 B7 107.3(3)
F1 B8 B12 121.2(4)
B3 B8 B12 107.3(3)
B4 B8 B12 107.0(3)
B7 B8 B12 59.6(3)
F1 B8 B9 121.7(4)
B3 B8 B9 107.0(3)
B4 B8 B9 59.4(3)
B7 B8 B9 107.1(3)
B12 B8 B9 59.6(3)
F2 B9 B4 122.2(4)
F2 B9 B5 121.9(4)
B4 B9 B5 59.6(3)
F2 B9 B12 121.9(4)
B4 B9 B12 107.5(4)
B5 B9 B12 107.7(3)
F2 B9 B10 121.4(4)
B4 B9 B10 107.5(3)
B5 B9 B10 59.6(3)
B12 B9 B10 60.5(3)
F2 B9 B8 122.2(4)
B4 B9 B8 59.5(3)
B5 B9 B8 107.3(3)
B12 B9 B8 60.2(3)
B10 B9 B8 108.4(4)
F3 B10 B6 122.2(4)
F3 B10 B5 122.7(4)
B6 B10 B5 59.7(3)
F3 B10 B11 121.6(4)
B6 B10 B11 59.5(3)
B5 B10 B11 107.2(3)
F3 B10 B9 122.6(4)
B6 B10 B9 107.2(3)
B5 B10 B9 59.9(3)
B11 B10 B9 107.2(3)
F3 B10 B12 122.1(4)
B6 B10 B12 106.8(3)
B5 B10 B12 107.1(3)
B11 B10 B12 59.5(3)
B9 B10 B12 59.6(3)
C2 B11 B6 59.0(3)
C2 B11 B7 58.1(3)
B6 B11 B7 107.2(3)
C2 B11 B12 105.1(3)
B6 B11 B12 108.4(4)
B7 B11 B12 59.9(3)
C2 B11 B10 105.9(3)
B6 B11 B10 60.1(3)
B7 B11 B10 108.5(3)
B12 B11 B10 61.0(3)
F4 B12 B7 122.0(4)
F4 B12 B11 122.4(4)
B7 B12 B11 60.0(3)
F4 B12 B9 121.8(4)
B7 B12 B9 107.4(4)
B11 B12 B9 107.5(3)
F4 B12 B8 121.2(4)
B7 B12 B8 59.4(3)
B11 B12 B8 107.6(3)
B9 B12 B8 60.2(3)
F4 B12 B10 122.4(4)
B7 B12 B10 107.4(3)
B11 B12 B10 59.5(3)
B9 B12 B10 60.0(3)
B8 B12 B10 108.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 B8 1.359(5)
F2 B9 1.360(6)
F3 B10 1.355(5)
F4 B12 1.362(6)
C1 C11 1.515(6)
C1 C2 1.681(6)
C1 B5 1.690(6)
C1 B6 1.701(6)
C1 B4 1.705(6)
C1 B3 1.706(6)
C2 C12 1.514(6)
C2 B7 1.691(6)
C2 B11 1.699(7)
C2 B6 1.707(6)
C2 B3 1.713(6)
B3 B4 1.758(8)
B3 B8 1.764(7)
B3 B7 1.767(8)
B4 B5 1.768(7)
B4 B9 1.772(7)
B4 B8 1.773(7)
B5 B6 1.770(7)
B5 B10 1.781(7)
B5 B9 1.786(7)
B6 B11 1.766(7)
B6 B10 1.776(7)
B7 B8 1.775(7)
B7 B12 1.778(7)
B7 B11 1.780(7)
B8 B12 1.801(8)
B8 B9 1.801(8)
B9 B12 1.791(8)
B9 B10 1.799(7)
B10 B11 1.782(7)
B10 B12 1.808(7)
B11 B12 1.782(7)
