#------------------------------------------------------------------------------
#$Date: 2019-11-25 11:50:14 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/03/4130330.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_4130330
loop_
_publ_author_name
'Zhou, Jing'
'Kuntze-Fechner, Maximilian W'
'Bertermann, Rüdiger'
'Paul, Ursula S. D.'
'Berthel, Johannes H. J.'
'Friedrich, Alexandra'
'Du, Zhenting'
'Marder, Todd B.'
'Radius, Udo'
_publ_section_title
;
 Preparing (Multi)Fluoroarenes as Building Blocks for Synthesis:
 Nickel-Catalyzed Borylation of Polyfluoroarenes via C-F Bond Cleavage.
;
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5250
_journal_page_last               5253
_journal_paper_doi               10.1021/jacs.6b02337
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C18 H26 B2 F2 O4'
_chemical_formula_sum            'C18 H26 B2 F2 O4'
_chemical_formula_weight         366.01
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 98.521(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.448(2)
_cell_length_b                   7.1660(7)
_cell_length_c                   12.5448(13)
_cell_measurement_reflns_used    7634
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.12
_cell_measurement_theta_min      3.00
_cell_volume                     1906.8(3)
_computing_cell_refinement       'Saint-NT v. 7.23'
_computing_data_collection       'APEX2 ver. 2014.1 (Bruker AXS)'
_computing_data_reduction        'Saint-NT v. 7.23'
_computing_molecular_graphics    'XP ver. 5.1 (Bruker AXS, 1998)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  helios
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10521
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.128
_diffrn_reflns_theta_min         1.920
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.7120
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'Sadabs 2014/3 (Bruker 2014)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.411
_exptl_crystal_size_mid          0.364
_exptl_crystal_size_min          0.243
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0335
_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)+(0.0391P)²+1.9043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0846
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1795
_reflns_number_total             1893
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b02337_si_002.cif
_cod_data_source_block           compound_2e'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4130330
_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   0.961
_shelx_estimated_absorpt_t_max   0.976
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1 C 0.54458(5) 0.87987(15) 0.46093(8) 0.0140(2) Uani 1 1 d . .
F1 F 0.38097(3) 1.02098(10) 0.39180(5) 0.02209(19) Uani 1 1 d . .
B1 B 0.59044(6) 0.74332(17) 0.41383(10) 0.0143(2) Uani 1 1 d . .
O1 O 0.56887(3) 0.64446(11) 0.32294(6) 0.0174(2) Uani 1 1 d . .
C2 C 0.48267(5) 0.89599(15) 0.40697(8) 0.0150(2) Uani 1 1 d . .
H2 H 0.4698 0.8263 0.3431 0.018 Uiso 1 1 calc R U
O2 O 0.65159(3) 0.70859(11) 0.45478(6) 0.01626(19) Uani 1 1 d . .
C3 C 0.44058(5) 1.01287(15) 0.44666(9) 0.0151(2) Uani 1 1 d . .
C7 C 0.59539(6) 0.32492(17) 0.35892(11) 0.0276(3) Uani 1 1 d . .
H7A H 0.5534 0.2904 0.3223 0.041 Uiso 1 1 calc R U
H7B H 0.5938 0.3442 0.4358 0.041 Uiso 1 1 calc R U
H7C H 0.6253 0.2247 0.3501 0.041 Uiso 1 1 calc R U
C6 C 0.61831(6) 0.47861(18) 0.19056(9) 0.0241(3) Uani 1 1 d . .
H6A H 0.5771 0.4348 0.1552 0.036 Uiso 1 1 calc R U
H6B H 0.6507 0.3866 0.1802 0.036 Uiso 1 1 calc R U
H6C H 0.6283 0.5982 0.1591 0.036 Uiso 1 1 calc R U
C5 C 0.67728(5) 0.59080(16) 0.37593(8) 0.0157(2) Uani 1 1 d . .
C4 C 0.61656(5) 0.50383(15) 0.31023(9) 0.0166(2) Uani 1 1 d . .
C9 C 0.72225(6) 0.45108(18) 0.43677(10) 0.0236(3) Uani 1 1 d . .
H9A H 0.7351 0.3599 0.3861 0.035 Uiso 1 1 calc R U
H9B H 0.7012 0.3865 0.4903 0.035 Uiso 1 1 calc R U
H9C H 0.7595 0.5165 0.4733 0.035 Uiso 1 1 calc R U
C8 C 0.71276(6) 0.71993(18) 0.30977(10) 0.0241(3) Uani 1 1 d . .
H8A H 0.7322 0.6463 0.2577 0.036 Uiso 1 1 calc R U
H8B H 0.7456 0.7866 0.3578 0.036 Uiso 1 1 calc R U
H8C H 0.6833 0.8102 0.2712 0.036 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'
F F 0.0171 0.0103 '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
C3 C1 C2 116.15(10) 5_676 .
C3 C1 B1 125.65(10) 5_676 .
C2 C1 B1 118.19(10) . .
O2 B1 O1 114.19(10) . .
O2 B1 C1 126.70(10) . .
O1 B1 C1 119.11(10) . .
B1 O1 C4 107.05(8) . .
C3 C2 C1 119.98(10) . .
C3 C2 H2 120.0 . .
C1 C2 H2 120.0 . .
B1 O2 C5 106.74(8) . .
F1 C3 C2 117.40(9) . .
F1 C3 C1 118.74(9) . 5_676
C2 C3 C1 123.86(10) . 5_676
C4 C7 H7A 109.5 . .
C4 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C4 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C4 C6 H6A 109.5 . .
C4 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C4 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
O2 C5 C9 108.35(8) . .
O2 C5 C8 106.62(9) . .
C9 C5 C8 110.14(9) . .
O2 C5 C4 102.58(8) . .
C9 C5 C4 114.85(10) . .
C8 C5 C4 113.57(9) . .
O1 C4 C6 108.07(9) . .
O1 C4 C7 106.41(9) . .
C6 C4 C7 110.49(10) . .
O1 C4 C5 102.08(8) . .
C6 C4 C5 115.34(9) . .
C7 C4 C5 113.57(10) . .
C5 C9 H9A 109.5 . .
C5 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C5 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C5 C8 H8A 109.5 . .
C5 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C5 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
C1 C3 1.3880(15) 5_676
C1 C2 1.4030(15) .
C1 B1 1.5640(16) .
F1 C3 1.3605(12) .
B1 O2 1.3588(14) .
B1 O1 1.3638(14) .
O1 C4 1.4613(13) .
C2 C3 1.3776(15) .
C2 H2 0.9500 .
O2 C5 1.4683(12) .
C3 C1 1.3880(15) 5_676
C7 C4 1.5182(16) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C6 C4 1.5181(15) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C5 C9 1.5156(15) .
C5 C8 1.5203(15) .
C5 C4 1.5638(15) .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
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
C3 C1 B1 O2 -0.40(18) 5_676 .
C2 C1 B1 O2 -179.68(10) . .
C3 C1 B1 O1 178.96(10) 5_676 .
C2 C1 B1 O1 -0.33(15) . .
O2 B1 O1 C4 10.58(12) . .
C1 B1 O1 C4 -168.85(9) . .
C3 C1 C2 C3 -0.23(17) 5_676 .
B1 C1 C2 C3 179.13(10) . .
O1 B1 O2 C5 7.85(12) . .
C1 B1 O2 C5 -172.77(10) . .
C1 C2 C3 F1 -179.14(9) . .
C1 C2 C3 C1 0.25(18) . 5_676
B1 O2 C5 C9 -143.14(10) . .
B1 O2 C5 C8 98.33(10) . .
B1 O2 C5 C4 -21.29(10) . .
B1 O1 C4 C6 -144.80(10) . .
B1 O1 C4 C7 96.51(11) . .
B1 O1 C4 C5 -22.78(10) . .
O2 C5 C4 O1 26.50(10) . .
C9 C5 C4 O1 143.81(9) . .
C8 C5 C4 O1 -88.16(10) . .
O2 C5 C4 C6 143.40(9) . .
C9 C5 C4 C6 -99.28(11) . .
C8 C5 C4 C6 28.74(13) . .
O2 C5 C4 C7 -87.62(10) . .
C9 C5 C4 C7 29.70(13) . .
C8 C5 C4 C7 157.72(10) . .
