#------------------------------------------------------------------------------
#$Date: 2022-01-19 01:54:07 +0200 (Wed, 19 Jan 2022) $
#$Revision: 272115 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/93/7709310.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_7709310
loop_
_publ_author_name
'Wang, Sisi'
'Wang, Zhaoli'
'Song, Wenting'
'Gao, Hu'
'Wu, Fan'
'Zhao, Yue'
'Chan, Kin Shing'
'Shen, Zhen'
_publ_section_title
;
 B-O-B Bridged BOPPY Derivatives: Synthesis, Structures, and
 Acid-Catalyzed Cis-Trans Isomeric Interconversion
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT04203C
_journal_year                    2022
_chemical_formula_sum            'C22 H21 B3 F6 N8'
_chemical_formula_weight         543.90
_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-2018/3
_audit_update_record
;
2021-06-21 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.98(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.593(13)
_cell_length_b                   17.946(12)
_cell_length_c                   15.446(10)
_cell_measurement_reflns_used    1816
_cell_measurement_temperature    199(2)
_cell_measurement_theta_max      43.11
_cell_measurement_theta_min      2.89
_cell_volume                     5510(6)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      199(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'BRUKER D8 VENTURE PHOTON II'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_av_unetI/netI     0.0745
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20895
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.184
_diffrn_reflns_theta_max         53.184
_diffrn_reflns_theta_min         2.886
_exptl_absorpt_coefficient_mu    0.600
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             2224
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.00092(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         4889
_refine_ls_number_restraints     324
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.1521
_refine_ls_R_factor_gt           0.0617
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0800P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1908
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1972
_reflns_number_total             4889
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt04203c2.cif
_cod_data_source_block           shenzhen_wss_3b_0m_a_sq
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7709310
_shelx_shelxl_version_number     2018/3
_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   0.942
_shelx_estimated_absorpt_t_max   0.942
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.38608(13) 0.66976(14) 0.85650(16) 0.1106(8) Uani 1 1 d . U . . .
B1 B 0.4229(3) 0.6556(3) 0.8037(3) 0.0833(13) Uani 1 1 d . U . . .
N1 N 0.39658(15) 0.69596(18) 0.7080(2) 0.0769(9) Uani 1 1 d . U . . .
C1 C 0.39481(19) 0.7725(2) 0.6935(3) 0.0806(11) Uani 1 1 d . U . . .
F2 F 0.49018(11) 0.66846(13) 0.85705(15) 0.1015(8) Uani 1 1 d . U . . .
B2 B 0.3168(3) 0.7641(3) 0.4223(4) 0.0831(13) Uani 1 1 d . U . . .
N2 N 0.34632(15) 0.74856(19) 0.5281(2) 0.0787(9) Uani 1 1 d . U . . .
C2 C 0.36891(19) 0.7990(2) 0.6020(3) 0.0802(11) Uani 1 1 d . U . . .
F3 F 0.26028(11) 0.80821(12) 0.39132(16) 0.0999(8) Uani 1 1 d . U . . .
N3 N 0.38131(14) 0.57542(18) 0.6631(2) 0.0741(8) Uani 1 1 d . U . . .
C3 C 0.3663(2) 0.8753(3) 0.5862(3) 0.0976(13) Uani 1 1 d . U . . .
H3 H 0.348814 0.893860 0.523626 0.117 Uiso 1 1 calc R U . . .
C4 C 0.3889(2) 0.9238(3) 0.6603(4) 0.1054(14) Uani 1 1 d . U . . .
H4 H 0.385922 0.975952 0.649138 0.126 Uiso 1 1 calc R U . . .
F4 F 0.36324(11) 0.79484(12) 0.39053(16) 0.0986(7) Uani 1 1 d . U . . .
N4 N 0.41156(16) 0.57568(19) 0.7624(2) 0.0847(9) Uani 1 1 d . U . . .
N5 N 0.32042(15) 0.63246(17) 0.4663(2) 0.0752(8) Uani 1 1 d . U . . .
C5 C 0.4158(2) 0.8973(3) 0.7507(4) 0.1039(14) Uani 1 1 d . U . . .
H5 H 0.432590 0.931440 0.801585 0.125 Uiso 1 1 calc R U . . .
N6 N 0.30069(15) 0.68234(17) 0.3905(2) 0.0783(9) Uani 1 1 d . U . . .
C6 C 0.4190(2) 0.8221(3) 0.7689(3) 0.0943(12) Uani 1 1 d . U . . .
H6 H 0.437331 0.804174 0.831787 0.113 Uiso 1 1 calc R U . . .
C7 C 0.37459(17) 0.6468(2) 0.6378(3) 0.0706(10) Uani 1 1 d . U . . .
N7 N 0.38833(17) 0.4329(2) 0.6742(3) 0.0913(10) Uani 1 1 d . U . . .
H7A H 0.374323 0.468129 0.631239 0.110 Uiso 0.299(5) 1 calc R U P A 2
C8 C 0.34678(18) 0.6743(2) 0.5428(3) 0.0723(10) Uani 1 1 d . U . . .
N8 N 0.26220(16) 0.5260(2) 0.3366(2) 0.0871(9) Uani 1 1 d . U . . .
H8A H 0.282998 0.528189 0.398175 0.105 Uiso 0.701(5) 1 calc R U P A 1
C9 C 0.4276(2) 0.5127(3) 0.8086(3) 0.0876(12) Uani 1 1 d . U . . .
H9 H 0.447845 0.515854 0.875196 0.105 Uiso 1 1 calc R U . . .
C10 C 0.4181(2) 0.4433(3) 0.7704(3) 0.0846(11) Uani 1 1 d . U . . .
C11 C 0.4333(2) 0.3737(3) 0.8156(3) 0.0893(12) Uani 1 1 d . U . . .
C12 C 0.4114(2) 0.3221(3) 0.7443(4) 0.1061(14) Uani 1 1 d . U . . .
H12 H 0.414004 0.269546 0.752083 0.127 Uiso 1 1 calc R U . . .
C13 C 0.3848(2) 0.3596(3) 0.6586(4) 0.1031(13) Uani 1 1 d . U . . .
C14 C 0.4668(2) 0.3621(3) 0.9191(3) 0.1030(14) Uani 1 1 d . U . . .
H14A H 0.469489 0.308642 0.932880 0.155 Uiso 1 1 calc R U . . .
H14B H 0.440662 0.386852 0.950334 0.155 Uiso 1 1 calc R U . . .
H14C H 0.512215 0.383241 0.942099 0.155 Uiso 1 1 calc R U . . .
C15 C 0.3559(3) 0.3254(3) 0.5618(4) 0.1365(19) Uani 1 1 d . U . . .
H15A H 0.364236 0.271571 0.566625 0.205 Uiso 1 1 calc R U . . .
H15B H 0.377456 0.347732 0.522705 0.205 Uiso 1 1 calc R U . . .
H15C H 0.307387 0.334676 0.533162 0.205 Uiso 1 1 calc R U . . .
C16 C 0.2698(2) 0.6579(3) 0.3042(3) 0.0854(11) Uani 1 1 d . U . . .
H16 H 0.258424 0.694457 0.255970 0.102 Uiso 1 1 calc R U . . .
C17 C 0.2519(2) 0.5852(3) 0.2748(3) 0.0852(11) Uani 1 1 d . U . . .
C18 C 0.2168(2) 0.5586(3) 0.1830(3) 0.1017(13) Uani 1 1 d . U . . .
C19 C 0.1946(3) 0.6043(3) 0.0957(3) 0.1340(19) Uani 1 1 d . U . . .
H19A H 0.161684 0.576139 0.043599 0.201 Uiso 1 1 calc R U . . .
H19B H 0.233528 0.616331 0.080635 0.201 Uiso 1 1 calc R U . . .
H19C H 0.173889 0.650507 0.105236 0.201 Uiso 1 1 calc R U . . .
C20 C 0.2073(3) 0.4840(3) 0.1920(4) 0.1148(16) Uani 1 1 d . U . . .
H20 H 0.185132 0.450913 0.141269 0.138 Uiso 1 1 calc R U . . .
C21 C 0.2345(2) 0.4640(3) 0.2853(4) 0.0991(13) Uani 1 1 d . U . . .
C22 C 0.2340(3) 0.3911(3) 0.3308(4) 0.1253(17) Uani 1 1 d . U . . .
H22A H 0.199945 0.358577 0.286149 0.188 Uiso 1 1 calc R U . . .
H22B H 0.223394 0.398945 0.386264 0.188 Uiso 1 1 calc R U . . .
H22C H 0.278363 0.367622 0.349895 0.188 Uiso 1 1 calc R U . . .
B3 B 0.3684(3) 0.5035(4) 0.6045(5) 0.0786(18) Uani 0.701(5) 1 d D U P A 1
F5 F 0.3016(2) 0.4978(2) 0.5437(3) 0.0914(13) Uani 0.701(5) 1 d D U P A 1
F6 F 0.4081(2) 0.50344(17) 0.5521(3) 0.0933(13) Uani 0.701(5) 1 d D U P A 1
B3A B 0.3057(6) 0.5413(9) 0.4492(11) 0.079(3) Uani 0.299(5) 1 d D U P A 2
F5A F 0.2671(6) 0.5178(6) 0.4975(8) 0.098(3) Uani 0.299(5) 1 d D U P A 2
F6A F 0.3662(5) 0.5037(4) 0.4790(7) 0.094(3) Uani 0.299(5) 1 d D U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0070 0.0029 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0583 0.0400 '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
_geom_angle_publ_flag
F1 B1 F2 109.6(4) . . ?
F1 B1 N1 113.8(4) . . ?
F2 B1 N1 113.7(4) . . ?
F1 B1 N4 112.5(4) . . ?
F2 B1 N4 111.1(4) . . ?
N1 B1 N4 95.7(3) . . ?
C7 N1 C1 122.9(3) . . ?
C7 N1 B1 110.5(3) . . ?
C1 N1 B1 126.6(3) . . ?
C2 C1 N1 118.6(4) . . ?
C2 C1 C6 120.2(4) . . ?
N1 C1 C6 121.2(4) . . ?
F3 B2 F4 108.2(4) . . ?
F3 B2 N2 114.8(4) . . ?
F4 B2 N2 113.1(4) . . ?
F3 B2 N6 112.2(4) . . ?
F4 B2 N6 111.6(4) . . ?
N2 B2 N6 96.6(3) . . ?
C8 N2 C2 121.9(3) . . ?
C8 N2 B2 109.4(3) . . ?
C2 N2 B2 128.8(4) . . ?
C1 C2 N2 119.2(4) . . ?
C1 C2 C3 119.4(4) . . ?
N2 C2 C3 121.4(4) . . ?
C7 N3 N4 105.5(3) . . ?
C7 N3 B3 131.3(4) . . ?
N4 N3 B3 122.9(4) . . ?
C4 C3 C2 120.2(5) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.2(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C9 N4 N3 120.0(4) . . ?
C9 N4 B1 127.5(4) . . ?
N3 N4 B1 112.4(3) . . ?
C8 N5 N6 105.5(3) . . ?
C8 N5 B3A 133.2(6) . . ?
N6 N5 B3A 121.2(6) . . ?
C4 C5 C6 121.1(5) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C16 N6 N5 120.2(3) . . ?
C16 N6 B2 127.1(4) . . ?
N5 N6 B2 112.6(3) . . ?
C5 C6 C1 118.9(5) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N3 C7 N1 115.7(3) . . ?
N3 C7 C8 125.7(4) . . ?
N1 C7 C8 118.6(4) . . ?
C13 N7 C10 107.2(4) . . ?
C13 N7 B3 132.4(4) . . ?
C10 N7 B3 120.3(4) . . ?
C13 N7 H7A 126.4 . . ?
C10 N7 H7A 126.4 . . ?
N5 C8 N2 115.9(3) . . ?
N5 C8 C7 125.3(4) . . ?
N2 C8 C7 118.8(4) . . ?
C21 N8 C17 108.1(4) . . ?
C21 N8 B3A 133.6(7) . . ?
C17 N8 B3A 118.2(6) . . ?
C21 N8 H8A 126.0 . . ?
C17 N8 H8A 126.0 . . ?
N4 C9 C10 126.4(4) . . ?
N4 C9 H9 116.8 . . ?
C10 C9 H9 116.8 . . ?
C9 C10 N7 121.1(4) . . ?
C9 C10 C11 129.3(4) . . ?
N7 C10 C11 109.6(4) . . ?
C12 C11 C10 105.1(4) . . ?
C12 C11 C14 129.6(4) . . ?
C10 C11 C14 125.4(4) . . ?
C11 C12 C13 108.7(5) . . ?
C11 C12 H12 125.6 . . ?
C13 C12 H12 125.6 . . ?
N7 C13 C12 109.4(5) . . ?
N7 C13 C15 123.5(5) . . ?
C12 C13 C15 127.1(5) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N6 C16 C17 127.8(4) . . ?
N6 C16 H16 116.1 . . ?
C17 C16 H16 116.1 . . ?
C16 C17 N8 123.2(4) . . ?
C16 C17 C18 128.4(4) . . ?
N8 C17 C18 108.2(4) . . ?
C20 C18 C17 105.8(4) . . ?
C20 C18 C19 128.5(5) . . ?
C17 C18 C19 125.7(5) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 C21 110.0(5) . . ?
C18 C20 H20 125.0 . . ?
C21 C20 H20 125.0 . . ?
N8 C21 C20 107.9(5) . . ?
N8 C21 C22 121.9(5) . . ?
C20 C21 C22 130.2(5) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F5 B3 F6 108.8(5) . . ?
F5 B3 N3 111.2(5) . . ?
F6 B3 N3 109.4(5) . . ?
F5 B3 N7 109.4(5) . . ?
F6 B3 N7 109.0(5) . . ?
N3 B3 N7 109.0(4) . . ?
F6A B3A F5A 111.3(12) . . ?
F6A B3A N8 110.2(10) . . ?
F5A B3A N8 107.7(10) . . ?
F6A B3A N5 109.2(9) . . ?
F5A B3A N5 109.4(10) . . ?
N8 B3A N5 109.0(9) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.366(5) . ?
B1 F2 1.381(5) . ?
B1 N1 1.541(6) . ?
B1 N4 1.551(6) . ?
N1 C7 1.333(4) . ?
N1 C1 1.390(5) . ?
C1 C2 1.385(5) . ?
C1 C6 1.395(5) . ?
B2 F3 1.375(5) . ?
B2 F4 1.392(5) . ?
B2 N2 1.530(6) . ?
B2 N6 1.543(6) . ?
N2 C8 1.351(5) . ?
N2 C2 1.387(5) . ?
C2 C3 1.388(5) . ?
N3 C7 1.331(5) . ?
N3 N4 1.413(4) . ?
N3 B3 1.539(7) . ?
C3 C4 1.368(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(6) . ?
C4 H4 0.9500 . ?
N4 C9 1.308(5) . ?
N5 C8 1.327(4) . ?
N5 N6 1.401(4) . ?
N5 B3A 1.668(16) . ?
C5 C6 1.375(6) . ?
C5 H5 0.9500 . ?
N6 C16 1.311(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.438(5) . ?
N7 C13 1.335(6) . ?
N7 C10 1.382(5) . ?
N7 B3 1.609(7) . ?
N7 H7A 0.8800 . ?
N8 C21 1.362(5) . ?
N8 C17 1.386(5) . ?
N8 B3A 1.646(16) . ?
N8 H8A 0.8800 . ?
C9 C10 1.359(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.404(6) . ?
C11 C12 1.375(6) . ?
C11 C14 1.489(6) . ?
C12 C13 1.392(6) . ?
C12 H12 0.9500 . ?
C13 C15 1.508(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.386(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.405(6) . ?
C18 C20 1.371(6) . ?
C18 C19 1.489(6) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.375(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.487(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
B3 F5 1.384(7) . ?
B3 F6 1.389(7) . ?
B3A F6A 1.381(12) . ?
B3A F5A 1.382(12) . ?
