#------------------------------------------------------------------------------
#$Date: 2019-11-25 15:54:59 +0200 (Mon, 25 Nov 2019) $
#$Revision: 241259 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/09/4130905.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_4130905
loop_
_publ_author_name
'Yang, Deng-Tao'
'Mellerup, Soren K.'
'Peng, Jin-Bao'
'Wang, Xiang'
'Li, Quan-Song'
'Wang, Suning'
_publ_section_title
;
 Substituent Directed Phototransformations of BN-Heterocycles: Elimination
 vs Isomerization via Selective B-C Bond Cleavage.
;
_journal_issue                   36
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11513
_journal_page_last               11516
_journal_paper_doi               10.1021/jacs.6b07899
_journal_volume                  138
_journal_year                    2016
_chemical_formula_sum            'C24 H15 B F5 N'
_chemical_formula_weight         423.18
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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                 111.064(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8288(5)
_cell_length_b                   8.7441(3)
_cell_length_c                   17.1220(6)
_cell_measurement_reflns_used    3972
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.56
_cell_measurement_theta_min      2.47
_cell_volume                     1932.05(12)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16541
_diffrn_reflns_theta_full        27.30
_diffrn_reflns_theta_max         27.30
_diffrn_reflns_theta_min         1.58
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_correction_T_min  0.9883
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0554P)²+0.3153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1274
_reflns_number_gt                2815
_reflns_number_total             4317
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja6b07899_si_007.cif
_cod_data_source_block           dy42
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4130905
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
B1 B 0.28045(14) 0.2512(2) 0.93177(12) 0.0340(4) Uani 1 1 d .
N1 N 0.27149(11) 0.43707(16) 0.92133(9) 0.0360(3) Uani 1 1 d .
F1 F 0.33385(8) 0.01050(12) 1.06604(7) 0.0532(3) Uani 1 1 d .
F2 F 0.21987(10) -0.07530(16) 1.15295(8) 0.0798(4) Uani 1 1 d .
F3 F 0.03753(10) 0.06380(18) 1.13291(8) 0.0795(4) Uani 1 1 d .
F4 F -0.03265(9) 0.28864(16) 1.01700(8) 0.0738(4) Uani 1 1 d .
F5 F 0.07762(8) 0.37746(14) 0.92751(8) 0.0634(4) Uani 1 1 d .
C1 C 0.40378(13) 0.2274(2) 0.97614(11) 0.0405(4) Uani 1 1 d .
H1A H 0.4187 0.1194 0.9868 0.049 Uiso 1 1 calc R
H1B H 0.4379 0.2623 0.9388 0.049 Uiso 1 1 calc R
C2 C 0.44542(13) 0.3132(2) 1.05646(11) 0.0416(5) Uani 1 1 d .
C3 C 0.52096(14) 0.2537(3) 1.12780(12) 0.0535(5) Uani 1 1 d .
H3A H 0.5462 0.1556 1.1262 0.064 Uiso 1 1 calc R
C4 C 0.55911(18) 0.3372(3) 1.20075(14) 0.0659(7) Uani 1 1 d .
H4A H 0.6097 0.2953 1.2477 0.079 Uiso 1 1 calc R
C5 C 0.52264(18) 0.4820(3) 1.20432(14) 0.0668(7) Uani 1 1 d .
H5A H 0.5490 0.5384 1.2535 0.080 Uiso 1 1 calc R
C6 C 0.44682(16) 0.5440(3) 1.13497(13) 0.0580(6) Uani 1 1 d .
H6A H 0.4217 0.6416 1.1379 0.070 Uiso 1 1 calc R
C7 C 0.40764(13) 0.4607(2) 1.06038(12) 0.0426(5) Uani 1 1 d .
C8 C 0.32996(13) 0.5295(2) 0.98486(12) 0.0400(4) Uani 1 1 d .
C9 C 0.31690(17) 0.6862(2) 0.97596(15) 0.0559(6) Uani 1 1 d .
H9A H 0.3561 0.7501 1.0192 0.067 Uiso 1 1 calc R
C10 C 0.24697(18) 0.7492(2) 0.90427(17) 0.0638(6) Uani 1 1 d .
H10A H 0.2379 0.8546 0.8994 0.077 Uiso 1 1 calc R
C11 C 0.19075(17) 0.6548(2) 0.83999(15) 0.0550(5) Uani 1 1 d .
H11A H 0.1440 0.6949 0.7905 0.066 Uiso 1 1 calc R
C12 C 0.20526(14) 0.5000(2) 0.85056(12) 0.0427(4) Uani 1 1 d .
H12A H 0.1677 0.4357 0.8069 0.051 Uiso 1 1 calc R
C13 C 0.21424(13) 0.20264(19) 0.99193(10) 0.0335(4) Uani 1 1 d .
C14 C 0.24332(13) 0.0871(2) 1.05050(11) 0.0384(4) Uani 1 1 d .
C15 C 0.18577(16) 0.0389(2) 1.09698(12) 0.0495(5) Uani 1 1 d .
C16 C 0.09333(16) 0.1077(3) 1.08688(12) 0.0509(5) Uani 1 1 d .
C17 C 0.05896(14) 0.2212(2) 1.02936(12) 0.0478(5) Uani 1 1 d .
C18 C 0.11904(14) 0.2654(2) 0.98394(11) 0.0407(4) Uani 1 1 d .
C19 C 0.23296(12) 0.17054(18) 0.84107(11) 0.0326(4) Uani 1 1 d .
C20 C 0.28980(14) 0.1608(2) 0.78872(12) 0.0491(5) Uani 1 1 d .
H20A H 0.3553 0.2050 0.8060 0.059 Uiso 1 1 calc R
C21 C 0.25289(16) 0.0881(3) 0.71209(13) 0.0592(6) Uani 1 1 d .
H21A H 0.2930 0.0856 0.6786 0.071 Uiso 1 1 calc R
C22 C 0.15707(15) 0.0193(2) 0.68500(12) 0.0497(5) Uani 1 1 d .
H22A H 0.1329 -0.0328 0.6343 0.060 Uiso 1 1 calc R
C23 C 0.09816(15) 0.0288(2) 0.73379(12) 0.0530(5) Uani 1 1 d .
H23A H 0.0324 -0.0147 0.7156 0.064 Uiso 1 1 calc R
C24 C 0.13574(14) 0.1027(2) 0.81020(12) 0.0455(5) Uani 1 1 d .
H24A H 0.0941 0.1072 0.8424 0.055 Uiso 1 1 calc R
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'
N N 0.0061 0.0033 '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
C1 B1 C19 113.11(14)
C1 B1 N1 101.89(14)
C19 B1 N1 109.91(14)
C1 B1 C13 113.61(15)
C19 B1 C13 111.12(14)
N1 B1 C13 106.56(13)
C12 N1 C8 119.49(16)
C12 N1 B1 120.35(15)
C8 N1 B1 120.16(14)
C2 C1 B1 111.26(15)
C3 C2 C7 118.48(19)
C3 C2 C1 122.78(18)
C7 C2 C1 118.73(17)
C4 C3 C2 121.3(2)
C5 C4 C3 120.1(2)
C4 C5 C6 120.1(2)
C5 C6 C7 120.4(2)
C6 C7 C2 119.58(19)
C6 C7 C8 120.49(19)
C2 C7 C8 119.88(17)
N1 C8 C9 118.88(18)
N1 C8 C7 119.48(16)
C9 C8 C7 121.61(18)
C10 C9 C8 121.1(2)
C11 C10 C9 119.3(2)
C12 C11 C10 118.3(2)
N1 C12 C11 122.8(2)
C14 C13 C18 112.36(16)
C14 C13 B1 123.86(15)
C18 C13 B1 123.58(15)
F1 C14 C13 120.75(16)
F1 C14 C15 114.75(16)
C13 C14 C15 124.50(17)
F2 C15 C16 119.28(18)
F2 C15 C14 120.69(19)
C16 C15 C14 120.03(18)
F3 C16 C17 120.64(19)
F3 C16 C15 120.60(19)
C17 C16 C15 118.76(17)
F4 C17 C16 119.97(17)
F4 C17 C18 120.83(19)
C16 C17 C18 119.21(18)
F5 C18 C17 114.79(16)
F5 C18 C13 120.07(15)
C17 C18 C13 125.13(17)
C24 C19 C20 115.00(16)
C24 C19 B1 123.79(15)
C20 C19 B1 121.19(15)
C21 C20 C19 122.64(18)
C22 C21 C20 120.30(19)
C23 C22 C21 118.84(18)
C22 C23 C24 120.29(18)
C23 C24 C19 122.90(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B1 C1 1.612(3)
B1 C19 1.615(3)
B1 N1 1.635(2)
B1 C13 1.661(2)
N1 C12 1.346(2)
N1 C8 1.363(2)
F1 C14 1.359(2)
F2 C15 1.347(2)
F3 C16 1.342(2)
F4 C17 1.343(2)
F5 C18 1.3507(19)
C1 C2 1.489(2)
C2 C3 1.392(3)
C2 C7 1.402(3)
C3 C4 1.377(3)
C4 C5 1.372(4)
C5 C6 1.381(3)
C6 C7 1.399(3)
C7 C8 1.480(3)
C8 C9 1.383(3)
C9 C10 1.376(3)
C10 C11 1.372(3)
C11 C12 1.371(3)
C13 C14 1.378(2)
C13 C18 1.387(2)
C14 C15 1.378(3)
C15 C16 1.366(3)
C16 C17 1.358(3)
C17 C18 1.382(3)
C19 C24 1.388(2)
C19 C20 1.391(2)
C20 C21 1.380(3)
C21 C22 1.375(3)
C22 C23 1.363(3)
C23 C24 1.382(3)
