#------------------------------------------------------------------------------
#$Date: 2019-11-25 09:29:43 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240612 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/00/4130018.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_4130018
loop_
_publ_author_name
'Longobardi, Lauren E.'
'Liu, Lei'
'Grimme, Stefan'
'Stephan, Douglas W.'
_publ_section_title
;
 Stable Borocyclic Radicals via Frustrated Lewis Pair Hydrogenations.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2500
_journal_page_last               2503
_journal_paper_doi               10.1021/jacs.5b12823
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C20 H8 B F5 O2'
_chemical_formula_sum            'C20 H8 B F5 O2'
_chemical_formula_weight         386.10
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_audit_creation_date             2015-12-07
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.455(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.047(2)
_cell_length_b                   14.854(5)
_cell_length_c                   15.221(6)
_cell_measurement_reflns_used    1856
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.47
_cell_measurement_theta_min      2.70
_cell_volume                     1579.8(9)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.03
_diffrn_measured_fraction_theta_full 0.9881
_diffrn_measured_fraction_theta_max 0.9881
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0967
_diffrn_reflns_av_unetI/netI     0.1042
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13656
_diffrn_reflns_theta_full        24.9981
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1045 before and 0.0821 after correction.
The Ratio of minimum to maximum transmission is 0.7634.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.6232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             776.6446
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.7486
_refine_diff_density_min         -0.5896
_refine_diff_density_rms         0.1596
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             10.5867
_refine_ls_goodness_of_fit_ref   1.0968
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    8
_refine_ls_number_parameters     252
_refine_ls_number_reflns         2748
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0968
_refine_ls_R_factor_all          0.1157
_refine_ls_R_factor_gt           0.0772
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0990P)²+3.0659P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1990
_refine_ls_wR_factor_ref         0.2236
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                1811
_reflns_number_total             2748
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            4-LEL059_0m.cif
_cod_data_source_block           LEL059_0m
_cod_original_cell_volume        1579.7(9)
_cod_database_code               4130018
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.03451) H1(0.02827) H3(0.03344) H4(0.02914) H5(0.03047)
 H8(0.02901) H6(0.03645) H7(0.0384)
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C1(H1), C3(H3), C4(H4), C5(H5), C8(H8), C6(H6), C7(H7)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 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_refinement_flags_posn
F3 F 0.7795(4) 0.78716(19) 1.28211(19) 0.0350(8) Uani 1.000000 .
F2 F 0.9160(4) 0.6197(2) 1.32490(18) 0.0332(8) Uani 1.000000 .
F1 F 0.9041(4) 0.49161(18) 1.19992(18) 0.0270(7) Uani 1.000000 .
O1 O 0.8178(4) 0.4286(2) 1.0304(2) 0.0201(8) Uani 1.000000 .
F5 F 0.6114(4) 0.69824(18) 0.98715(18) 0.0288(7) Uani 1.000000 .
F4 F 0.6270(4) 0.82521(18) 1.1122(2) 0.0336(8) Uani 1.000000 .
C2 C 0.5262(7) 0.4653(4) 0.6454(3) 0.0282(12) Uani 1.000000 .
H2 H 0.4731(7) 0.5083(4) 0.6030(3) 0.034510 Uiso 1.000000 R
C18 C 0.7717(7) 0.7237(3) 1.2194(3) 0.0253(12) Uani 1.000000 .
C17 C 0.8409(6) 0.6383(3) 1.2415(3) 0.0219(11) Uani 1.000000 .
C16 C 0.8319(6) 0.5736(3) 1.1755(3) 0.0194(11) Uani 1.000000 .
C15 C 0.7567(6) 0.5894(3) 1.0879(3) 0.0207(11) Uani 1.000000 .
B1 B 0.7513(7) 0.5161(3) 1.0150(4) 0.0180(12) Uani 1.000000 .
C9 C 0.7843(6) 0.3876(3) 0.9474(3) 0.0198(10) Uani 1.000000 .
C14 C 0.8226(6) 0.2968(3) 0.9266(3) 0.0199(11) Uani 1.000000 .
C13 C 0.7736(6) 0.2708(3) 0.8372(3) 0.0176(10) Uani 1.000000 .
C12 C 0.6870(6) 0.3355(3) 0.7710(3) 0.0196(10) Uani 1.000000 .
C11 C 0.6542(6) 0.4263(3) 0.7956(3) 0.0201(11) Uani 1.000000 .
C1 C 0.5752(7) 0.4898(3) 0.7326(3) 0.0233(11) Uani 1.000000 .
H1 H 0.5555(7) 0.5501(3) 0.7504(3) 0.028270 Uiso 1.000000 R
C3 C 0.5555(7) 0.3761(3) 0.6198(3) 0.0279(12) Uani 1.000000 .
H3 H 0.5213(7) 0.3587(3) 0.5598(3) 0.033440 Uiso 1.000000 R
C4 C 0.6334(7) 0.3137(3) 0.6810(3) 0.0240(11) Uani 1.000000 .
H4 H 0.6518(7) 0.2537(3) 0.6620(3) 0.029140 Uiso 1.000000 R
C10 C 0.7038(6) 0.4475(3) 0.8870(3) 0.0192(10) Uani 1.000000 .
O2 O 0.6802(4) 0.5299(2) 0.9271(2) 0.0200(8) Uani 1.000000 .
C5 C 0.8136(7) 0.1814(3) 0.8154(3) 0.0255(12) Uani 1.000000 .
H5 H 0.7820(7) 0.1615(3) 0.7560(3) 0.030470 Uiso 1.000000 R
C20 C 0.6883(6) 0.6765(3) 1.0698(3) 0.0199(11) Uani 1.000000 .
C19 C 0.6946(7) 0.7425(3) 1.1339(3) 0.0224(11) Uani 1.000000 .
C8 C 0.9082(7) 0.2353(3) 0.9912(3) 0.0245(11) Uani 1.000000 .
H8 H 0.9408(7) 0.2538(3) 1.0511(3) 0.029010 Uiso 1.000000 R
C6 C 0.8973(7) 0.1223(3) 0.8782(3) 0.0296(12) Uani 1.000000 .
H6 H 0.9240(7) 0.0625(3) 0.8614(3) 0.036450 Uiso 1.000000 R
C7 C 0.9435(8) 0.1487(4) 0.9663(4) 0.0317(13) Uani 1.000000 .
H7 H 0.9996(8) 0.1067(4) 1.0091(4) 0.038400 Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 O1 B1 104.0(4)
C1 C2 H2 120.3(3)
C3 C2 H2 120.3(3)
C3 C2 C1 119.4(5)
C17 C18 F3 119.4(4)
C19 C18 F3 120.5(4)
C19 C18 C17 120.1(4)
C18 C17 F2 120.2(4)
C16 C17 F2 121.3(4)
C16 C17 C18 118.5(4)
C17 C16 F1 116.4(4)
C15 C16 F1 120.0(4)
C15 C16 C17 123.6(4)
B1 C15 C16 122.5(4)
C20 C15 C16 115.2(4)
C20 C15 B1 122.2(4)
C15 B1 O1 124.0(4)
O2 B1 O1 111.9(4)
O2 B1 C15 124.0(4)
C14 C9 O1 127.0(4)
C10 C9 O1 109.7(4)
C10 C9 C14 123.3(4)
C13 C14 C9 116.4(4)
C8 C14 C9 122.2(4)
C8 C14 C13 121.4(4)
C12 C13 C14 120.6(4)
C5 C13 C14 117.0(4)
C5 C13 C12 122.4(4)
C11 C12 C13 120.4(4)
C4 C12 C13 123.4(4)
C4 C12 C11 116.2(4)
C1 C11 C12 121.2(4)
C10 C11 C12 115.9(4)
C10 C11 C1 122.9(4)
C11 C1 C2 120.5(5)
H1 C1 C2 119.8(3)
H1 C1 C11 119.8(3)
H3 C3 C2 119.7(3)
C4 C3 C2 120.5(5)
C4 C3 H3 119.7(3)
C3 C4 C12 122.3(5)
H4 C4 C12 118.8(3)
H4 C4 C3 118.8(3)
C11 C10 C9 123.2(4)
O2 C10 C9 110.1(4)
O2 C10 C11 126.6(4)
C10 O2 B1 104.2(4)
H5 C5 C13 119.3(3)
C6 C5 C13 121.4(5)
C6 C5 H5 119.3(3)
C15 C20 F5 119.7(4)
C19 C20 F5 117.6(4)
C19 C20 C15 122.7(4)
C18 C19 F4 120.2(4)
C20 C19 F4 119.9(4)
C20 C19 C18 119.9(4)
H8 C8 C14 120.4(3)
C7 C8 C14 119.1(5)
C7 C8 H8 120.4(3)
H6 C6 C5 119.5(3)
C7 C6 C5 121.0(5)
C7 C6 H6 119.5(3)
C6 C7 C8 120.1(5)
H7 C7 C8 119.9(3)
H7 C7 C6 119.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F3 C18 1.338(5)
F2 C17 1.340(5)
F1 C16 1.353(5)
O1 B1 1.390(6)
O1 C9 1.394(5)
F5 C20 1.343(5)
F4 C19 1.343(5)
C2 H2 0.9500
C2 C1 1.376(7)
C2 C3 1.404(7)
C18 C17 1.385(7)
C18 C19 1.372(7)
C17 C16 1.386(7)
C16 C15 1.389(7)
C15 B1 1.553(7)
C15 C20 1.396(7)
B1 O2 1.381(6)
C9 C14 1.420(6)
C9 C10 1.350(7)
C14 C13 1.414(7)
C14 C8 1.419(7)
C13 C12 1.467(6)
C13 C5 1.405(6)
C12 C11 1.427(7)
C12 C4 1.411(7)
C11 C1 1.407(7)
C11 C10 1.424(7)
C1 H1 0.9500
C3 H3 0.9500
C3 C4 1.377(7)
C4 H4 0.9500
C10 O2 1.388(5)
C5 H5 0.9500
C5 C6 1.374(7)
C20 C19 1.380(7)
C8 H8 0.9500
C8 C7 1.373(7)
C6 H6 0.9500
C6 C7 1.394(7)
C7 H7 0.9500
