#------------------------------------------------------------------------------
#$Date: 2016-03-22 13:50:58 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178980 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/03/4120324.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_4120324
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            'C5 H12 B10 F4'
_chemical_formula_weight         256.25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.454(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4217(17)
_cell_length_b                   14.077(3)
_cell_length_c                   12.067(3)
_cell_measurement_reflns_used    81
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     1235.6(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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1025
_diffrn_reflns_av_sigmaI/netI    0.0928
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10596
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7056
_exptl_absorpt_correction_T_min  0.5041
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_platon_squeeze_details
;
;
_refine_diff_density_max         0.839
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0829
_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)+(0.1584P)²+0.2763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2389
_refine_ls_wR_factor_ref         0.2573
_reflns_number_gt                1588
_reflns_number_total             2229
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja405808t_si_001_2.cif
_cod_data_source_block           2g
_cod_database_code               4120324
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F 0.4908(3) 0.59195(14) 0.6744(2) 0.0653(7) Uani 1 1 d .
F2 F 0.0618(3) 0.53764(15) 0.65574(19) 0.0609(7) Uani 1 1 d .
F3 F 0.0371(3) 0.37123(18) 0.8357(2) 0.0704(8) Uani 1 1 d .
F4 F 0.3341(3) 0.53977(15) 0.89806(18) 0.0648(8) Uani 1 1 d .
C1 C 0.3838(4) 0.3148(2) 0.6280(3) 0.0350(8) Uani 1 1 d .
C2 C 0.5218(4) 0.3152(2) 0.7520(2) 0.0337(7) Uani 1 1 d .
C11 C 0.4393(5) 0.2316(2) 0.5602(3) 0.0530(10) Uani 1 1 d .
H11A H 0.3377 0.1876 0.5391 0.064 Uiso 1 1 calc R
H11B H 0.4757 0.2544 0.4920 0.064 Uiso 1 1 calc R
C12 C 0.6009(6) 0.1833(3) 0.6381(4) 0.0688(13) Uani 1 1 d .
H12A H 0.5691 0.1176 0.6488 0.083 Uiso 1 1 calc R
H12B H 0.7064 0.1837 0.6018 0.083 Uiso 1 1 calc R
C13 C 0.6536(5) 0.2309(2) 0.7529(3) 0.0493(9) Uani 1 1 d .
H13A H 0.7799 0.2528 0.7654 0.059 Uiso 1 1 calc R
H13B H 0.6414 0.1866 0.8125 0.059 Uiso 1 1 calc R
B3 B 0.5492(5) 0.3999(2) 0.6558(3) 0.0390(9) Uani 1 1 d .
H3 H 0.6681 0.4046 0.6142 0.047 Uiso 1 1 calc R
B4 B 0.3236(6) 0.4264(3) 0.5832(3) 0.0404(9) Uani 1 1 d .
H4 H 0.2953 0.4493 0.4943 0.048 Uiso 1 1 calc R
B5 B 0.1675(5) 0.3516(3) 0.6366(3) 0.0413(9) Uani 1 1 d .
H5 H 0.0394 0.3262 0.5826 0.050 Uiso 1 1 calc R
B6 B 0.3002(5) 0.2795(3) 0.7435(3) 0.0395(9) Uani 1 1 d .
H6 H 0.2582 0.2064 0.7585 0.047 Uiso 1 1 calc R
B7 B 0.5688(5) 0.4271(3) 0.8012(3) 0.0382(9) Uani 1 1 d .
H7 H 0.6995 0.4504 0.8542 0.046 Uiso 1 1 calc R
B8 B 0.4373(5) 0.5021(3) 0.6937(3) 0.0395(9) Uani 1 1 d .
B9 B 0.1977(5) 0.4714(3) 0.6827(3) 0.0384(9) Uani 1 1 d .
B10 B 0.1851(5) 0.3788(3) 0.7835(3) 0.0436(10) Uani 1 1 d .
B11 B 0.4142(5) 0.3517(3) 0.8553(3) 0.0403(9) Uani 1 1 d .
H11 H 0.4458 0.3262 0.9432 0.048 Uiso 1 1 calc R
B12 B 0.3508(5) 0.4720(3) 0.8196(3) 0.0388(9) 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 107.8(3)
C11 C1 B4 128.4(3)
C2 C1 B4 111.5(2)
C11 C1 B3 112.6(3)
C2 C1 B3 61.39(19)
B4 C1 B3 62.8(2)
C11 C1 B6 113.1(3)
C2 C1 B6 61.15(19)
B4 C1 B6 114.5(2)
B3 C1 B6 114.1(2)
C11 C1 B5 128.3(3)
C2 C1 B5 111.6(2)
B4 C1 B5 63.0(2)
B3 C1 B5 115.1(2)
B6 C1 B5 62.7(2)
C13 C2 C1 106.6(2)
C13 C2 B11 128.6(3)
C1 C2 B11 112.0(2)
C13 C2 B7 129.0(3)
C1 C2 B7 111.8(2)
B11 C2 B7 63.5(2)
C13 C2 B6 112.2(3)
C1 C2 B6 61.49(19)
B11 C2 B6 62.7(2)
B7 C2 B6 115.1(2)
C13 C2 B3 112.5(3)
C1 C2 B3 61.13(19)
B11 C2 B3 115.3(2)
B7 C2 B3 62.9(2)
B6 C2 B3 114.2(2)
C12 C11 C1 105.9(3)
C13 C12 C11 113.2(3)
C12 C13 C2 106.6(3)
C1 B3 C2 57.49(18)
C1 B3 B8 105.5(3)
C2 B3 B8 105.5(2)
C1 B3 B4 58.4(2)
C2 B3 B4 104.8(2)
B8 B3 B4 60.6(2)
C1 B3 B7 105.2(2)
C2 B3 B7 58.29(19)
B8 B3 B7 61.2(2)
B4 B3 B7 109.1(3)
C1 B4 B3 58.80(19)
C1 B4 B9 104.8(2)
B3 B4 B9 108.3(2)
C1 B4 B5 58.9(2)
B3 B4 B5 108.4(3)
B9 B4 B5 59.9(2)
C1 B4 B8 105.1(2)
B3 B4 B8 59.7(2)
B9 B4 B8 61.1(2)
B5 B4 B8 109.2(3)
C1 B5 B9 104.2(3)
C1 B5 B4 58.0(2)
B9 B5 B4 60.0(2)
C1 B5 B6 58.63(19)
B9 B5 B6 107.3(3)
B4 B5 B6 107.1(3)
C1 B5 B10 103.9(3)
B9 B5 B10 60.5(2)
B4 B5 B10 107.8(3)
B6 B5 B10 58.9(2)
C2 B6 C1 57.37(18)
C2 B6 B10 105.4(2)
C1 B6 B10 105.5(2)
C2 B6 B11 58.2(2)
C1 B6 B11 105.0(2)
B10 B6 B11 61.1(2)
C2 B6 B5 105.3(2)
C1 B6 B5 58.7(2)
B10 B6 B5 61.0(2)
B11 B6 B5 109.8(3)
C2 B7 B3 58.82(18)
C2 B7 B11 58.06(19)
B3 B7 B11 107.6(2)
C2 B7 B12 104.0(2)
B3 B7 B12 107.4(3)
B11 B7 B12 60.0(2)
C2 B7 B8 104.4(2)
B3 B7 B8 59.2(2)
B11 B7 B8 108.5(3)
B12 B7 B8 60.6(2)
F1 B8 B3 123.0(3)
F1 B8 B4 122.6(3)
B3 B8 B4 59.8(2)
F1 B8 B7 122.2(3)
B3 B8 B7 59.6(2)
B4 B8 B7 107.2(2)
F1 B8 B9 121.8(3)
B3 B8 B9 107.0(2)
B4 B8 B9 59.3(2)
B7 B8 B9 107.2(2)
F1 B8 B12 121.7(3)
B3 B8 B12 106.8(2)
B4 B8 B12 107.0(2)
B7 B8 B12 59.4(2)
B9 B8 B12 59.9(2)
F2 B9 B5 122.2(3)
F2 B9 B4 123.0(3)
B5 B9 B4 60.1(2)
F2 B9 B10 121.4(3)
B5 B9 B10 60.3(2)
B4 B9 B10 107.7(2)
F2 B9 B12 121.0(3)
B5 B9 B12 107.9(2)
B4 B9 B12 107.4(2)
B10 B9 B12 59.5(2)
F2 B9 B8 121.5(3)
B5 B9 B8 108.1(3)
B4 B9 B8 59.6(2)
B10 B9 B8 107.8(3)
B12 B9 B8 60.1(2)
F3 B10 B6 122.7(3)
F3 B10 B11 122.0(3)
B6 B10 B11 59.7(2)
F3 B10 B12 121.2(3)
B6 B10 B12 107.6(3)
B11 B10 B12 59.9(2)
F3 B10 B5 121.9(3)
B6 B10 B5 60.1(2)
B11 B10 B5 108.0(3)
B12 B10 B5 108.0(3)
F3 B10 B9 121.3(3)
B6 B10 B9 107.3(3)
B11 B10 B9 108.1(3)
B12 B10 B9 60.6(2)
B5 B10 B9 59.3(2)
C2 B11 B6 59.1(2)
C2 B11 B7 58.44(19)
B6 B11 B7 108.0(2)
C2 B11 B12 104.5(2)
B6 B11 B12 107.4(3)
B7 B11 B12 60.3(2)
C2 B11 B10 104.5(2)
B6 B11 B10 59.2(2)
B7 B11 B10 108.4(3)
B12 B11 B10 60.1(2)
F4 B12 B11 123.4(3)
F4 B12 B10 121.8(3)
B11 B12 B10 60.0(2)
F4 B12 B7 122.7(3)
B11 B12 B7 59.7(2)
B10 B12 B7 107.8(3)
F4 B12 B9 120.6(3)
B11 B12 B9 107.7(2)
B10 B12 B9 59.9(2)
B7 B12 B9 107.7(2)
F4 B12 B8 120.8(3)
B11 B12 B8 107.7(2)
B10 B12 B8 108.0(2)
B7 B12 B8 60.0(2)
B9 B12 B8 59.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 B8 1.359(4)
F2 B9 1.365(4)
F3 B10 1.375(4)
F4 B12 1.368(4)
C1 C11 1.531(4)
C1 C2 1.637(4)
C1 B4 1.693(5)
C1 B3 1.700(5)
C1 B6 1.709(5)
C1 B5 1.709(5)
C2 C13 1.537(4)
C2 B11 1.688(5)
C2 B7 1.695(5)
C2 B6 1.703(5)
C2 B3 1.705(4)
C11 C12 1.528(5)
C12 C13 1.518(5)
B3 B8 1.766(5)
B3 B4 1.769(5)
B3 B7 1.773(5)
B4 B9 1.777(5)
B4 B5 1.778(6)
B4 B8 1.782(5)
B5 B9 1.776(5)
B5 B6 1.779(5)
B5 B10 1.794(6)
B6 B10 1.756(5)
B6 B11 1.765(5)
B7 B11 1.780(5)
B7 B12 1.792(5)
B7 B8 1.803(6)
B8 B9 1.810(5)
B8 B12 1.813(5)
B9 B10 1.798(5)
B9 B12 1.809(5)
B10 B11 1.789(6)
B10 B12 1.791(5)
B11 B12 1.787(5)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 0.500 0.000 8.5 0.2
2 0.500 0.000 0.500 8.4 0.2
