#------------------------------------------------------------------------------
#$Date: 2022-01-19 01:54:07 +0200 (Wed, 19 Jan 2022) $
#$Revision: 272115 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/93/7709312.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_7709312
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_moiety         'C22 H18 B4 Br2 F6 N8 O'
_chemical_formula_sum            'C22 H18 B4 Br2 F6 N8 O'
_chemical_formula_weight         727.50
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-06-21 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.285(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6730(10)
_cell_length_b                   24.2903(19)
_cell_length_c                   8.7967(8)
_cell_measurement_reflns_used    4818
_cell_measurement_temperature    193.0
_cell_measurement_theta_max      60.221
_cell_measurement_theta_min      3.166
_cell_volume                     2585.6(4)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      193.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9672
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.605
_diffrn_reflns_theta_min         3.166
_diffrn_source_current           2.86
_diffrn_source_power             0.1993134
_diffrn_source_voltage           69.69
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.099
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0871 before and 0.0590 after correction.
The Ratio of minimum to maximum transmission is 0.8576.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.869
_exptl_crystal_description       block
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2873
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0338P)²+3.9192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0902
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2301
_reflns_number_total             2873
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt04203c2.cif
_cod_data_source_block           a
_cod_database_code               7709312
_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_max   0.747
_shelx_estimated_absorpt_t_min   0.727
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C1(H1)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C8(H8A,H8B,H8C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Br1 Br 0.67897(3) 0.96762(2) 0.78099(4) 0.03723(12) Uani 1 1 d . . . . .
F1 F 0.75030(13) 0.63013(7) 0.61055(19) 0.0359(4) Uani 1 1 d . . . . .
F2 F 0.59304(14) 0.62848(7) 0.67936(18) 0.0354(4) Uani 1 1 d . . . . .
F3 F 0.40658(13) 0.78260(7) 0.4253(2) 0.0420(4) Uani 1 1 d . . . . .
O1 O 0.500000 0.81333(11) 0.250000 0.0420(8) Uani 1 2 d S T P . .
N2 N 0.63835(17) 0.71383(9) 0.5686(2) 0.0251(5) Uani 1 1 d . . . . .
N1 N 0.57483(17) 0.63995(8) 0.3992(2) 0.0230(4) Uani 1 1 d . . . . .
N3 N 0.56892(17) 0.73249(8) 0.4221(2) 0.0241(5) Uani 1 1 d . . . . .
N4 N 0.58028(17) 0.82724(9) 0.5367(2) 0.0233(4) Uani 1 1 d . . . . .
C4 C 0.5369(2) 0.68810(10) 0.3314(3) 0.0217(5) Uani 1 1 d . . . . .
C3 C 0.5400(2) 0.58963(10) 0.3243(3) 0.0239(5) Uani 1 1 d . . . . .
C6 C 0.6603(2) 0.80557(11) 0.6690(3) 0.0242(5) Uani 1 1 d . . . . .
C7 C 0.7057(2) 0.84892(11) 0.7762(3) 0.0259(6) Uani 1 1 d . . . . .
C2 C 0.5812(2) 0.54002(11) 0.3968(3) 0.0297(6) Uani 1 1 d . . . . .
H2 H 0.636816 0.539827 0.496895 0.036 Uiso 1 1 calc R U . . .
C5 C 0.6822(2) 0.75014(11) 0.6815(3) 0.0255(6) Uani 1 1 d . . . . .
H5 H 0.732162 0.736998 0.777809 0.031 Uiso 1 1 calc R U . . .
C9 C 0.6520(2) 0.89527(11) 0.7043(3) 0.0267(6) Uani 1 1 d . . . . .
C11 C 0.4931(2) 0.91901(11) 0.4477(3) 0.0312(6) Uani 1 1 d . . . . .
H11A H 0.533089 0.943895 0.396498 0.047 Uiso 1 1 calc R U . . .
H11B H 0.453442 0.940621 0.507355 0.047 Uiso 1 1 calc R U . . .
H11C H 0.440198 0.897127 0.366259 0.047 Uiso 1 1 calc R U . . .
C1 C 0.5411(2) 0.49129(11) 0.3227(3) 0.0334(6) Uani 1 1 d . . . . .
H1 H 0.569681 0.457338 0.371379 0.040 Uiso 1 1 calc R U . . .
C8 C 0.7915(2) 0.84501(12) 0.9341(3) 0.0315(6) Uani 1 1 d . . . . .
H8A H 0.758763 0.854697 1.018356 0.047 Uiso 1 1 calc R U . . .
H8B H 0.852090 0.870466 0.936983 0.047 Uiso 1 1 calc R U . . .
H8C H 0.820150 0.807303 0.950618 0.047 Uiso 1 1 calc R U . . .
C10 C 0.5731(2) 0.88165(11) 0.5586(3) 0.0252(5) Uani 1 1 d . . . . .
B2 B 0.5087(3) 0.79158(12) 0.3978(4) 0.0266(6) Uani 1 1 d . . . . .
B1 B 0.6453(2) 0.64921(12) 0.5772(3) 0.0249(6) 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 0.0137 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'
Br Br -0.9338 1.0006 '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'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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
B2 O1 B2 134.9(3) 2_655 . ?
N3 N2 B1 112.15(19) . . ?
C5 N2 N3 118.9(2) . . ?
C5 N2 B1 128.7(2) . . ?
C4 N1 C3 122.3(2) . . ?
C4 N1 B1 110.0(2) . . ?
C3 N1 B1 127.0(2) . . ?
N2 N3 B2 123.6(2) . . ?
C4 N3 N2 106.57(19) . . ?
C4 N3 B2 126.5(2) . . ?
C6 N4 B2 123.7(2) . . ?
C10 N4 C6 108.3(2) . . ?
C10 N4 B2 127.9(2) . . ?
N1 C4 C4 118.60(13) . 2_655 ?
N3 C4 N1 115.9(2) . . ?
N3 C4 C4 125.47(14) . 2_655 ?
C3 C3 N1 118.79(13) 2_655 . ?
C2 C3 N1 121.3(2) . . ?
C2 C3 C3 119.93(16) . 2_655 ?
N4 C6 C7 108.9(2) . . ?
C5 C6 N4 121.0(2) . . ?
C5 C6 C7 130.1(2) . . ?
C6 C7 C8 127.8(2) . . ?
C9 C7 C6 104.8(2) . . ?
C9 C7 C8 127.4(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 H2 120.2 . . ?
N2 C5 C6 124.4(2) . . ?
N2 C5 H5 117.8 . . ?
C6 C5 H5 117.8 . . ?
C7 C9 Br1 126.3(2) . . ?
C7 C9 C10 110.3(2) . . ?
C10 C9 Br1 123.4(2) . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
C2 C1 C1 120.51(16) . 2_655 ?
C2 C1 H1 119.7 . . ?
C1 C1 H1 119.7 2_655 . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N4 C10 C9 107.5(2) . . ?
N4 C10 C11 124.6(2) . . ?
C9 C10 C11 127.8(2) . . ?
F3 B2 N3 105.3(2) . . ?
F3 B2 N4 107.7(2) . . ?
O1 B2 F3 113.8(2) . . ?
O1 B2 N3 111.6(2) . . ?
O1 B2 N4 113.1(2) . . ?
N4 B2 N3 104.48(19) . . ?
F1 B1 F2 111.7(2) . . ?
F1 B1 N2 112.9(2) . . ?
F1 B1 N1 113.4(2) . . ?
F2 B1 N2 111.7(2) . . ?
F2 B1 N1 111.2(2) . . ?
N1 B1 N2 95.07(19) . . ?
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
Br1 C9 1.877(3) . ?
F1 B1 1.357(3) . ?
F2 B1 1.361(3) . ?
F3 B2 1.402(4) . ?
O1 B2 1.377(3) . ?
O1 B2 1.377(3) 2_655 ?
N2 N3 1.403(3) . ?
N2 C5 1.320(3) . ?
N2 B1 1.573(4) . ?
N1 C4 1.336(3) . ?
N1 C3 1.397(3) . ?
N1 B1 1.571(3) . ?
N3 C4 1.331(3) . ?
N3 B2 1.610(4) . ?
N4 C6 1.400(3) . ?
N4 C10 1.343(3) . ?
N4 B2 1.551(3) . ?
C4 C4 1.460(5) 2_655 ?
C3 C3 1.396(5) 2_655 ?
C3 C2 1.391(3) . ?
C6 C7 1.417(3) . ?
C6 C5 1.372(4) . ?
C7 C9 1.369(4) . ?
C7 C8 1.491(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.374(4) . ?
C5 H5 0.9500 . ?
C9 C10 1.411(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C10 1.488(4) . ?
C1 C1 1.389(6) 2_655 ?
C1 H1 0.9500 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C9 C10 N4 176.34(19) . . . . ?
Br1 C9 C10 C11 -4.9(4) . . . . ?
N2 N3 C4 N1 1.1(3) . . . . ?
N2 N3 C4 C4 179.6(3) . . . 2_655 ?
N2 N3 B2 F3 -90.3(3) . . . . ?
N2 N3 B2 O1 145.7(2) . . . . ?
N2 N3 B2 N4 23.1(3) . . . . ?
N1 C3 C2 C1 176.9(2) . . . . ?
N3 N2 C5 C6 3.4(4) . . . . ?
N3 N2 B1 F1 123.4(2) . . . . ?
N3 N2 B1 F2 -109.8(2) . . . . ?
N3 N2 B1 N1 5.4(3) . . . . ?
N4 C6 C7 C9 -0.5(3) . . . . ?
N4 C6 C7 C8 178.6(2) . . . . ?
N4 C6 C5 N2 5.7(4) . . . . ?
C4 N1 C3 C3 -2.2(4) . . . 2_655 ?
C4 N1 C3 C2 179.6(2) . . . . ?
C4 N1 B1 F1 -122.2(2) . . . . ?
C4 N1 B1 F2 111.0(2) . . . . ?
C4 N1 B1 N2 -4.6(3) . . . . ?
C4 N3 B2 F3 66.2(3) . . . . ?
C4 N3 B2 O1 -57.8(3) . . . . ?
C4 N3 B2 N4 179.6(2) . . . . ?
C3 N1 C4 N3 173.8(2) . . . . ?
C3 N1 C4 C4 -4.9(4) . . . 2_655 ?
C3 N1 B1 F1 67.2(3) . . . . ?
C3 N1 B1 F2 -59.6(3) . . . . ?
C3 N1 B1 N2 -175.2(2) . . . . ?
C3 C3 C2 C1 -1.3(5) 2_655 . . . ?
C3 C2 C1 C1 -0.7(5) . . . 2_655 ?
C6 N4 C10 C9 1.9(3) . . . . ?
C6 N4 C10 C11 -176.8(2) . . . . ?
C6 N4 B2 F3 97.7(3) . . . . ?
C6 N4 B2 O1 -135.5(2) . . . . ?
C6 N4 B2 N3 -13.9(3) . . . . ?
C6 C7 C9 Br1 -176.94(19) . . . . ?
C6 C7 C9 C10 1.7(3) . . . . ?
C7 C6 C5 N2 -176.2(3) . . . . ?
C7 C9 C10 N4 -2.3(3) . . . . ?
C7 C9 C10 C11 176.4(3) . . . . ?
C5 N2 N3 C4 179.9(2) . . . . ?
C5 N2 N3 B2 -19.7(3) . . . . ?
C5 N2 B1 F1 -61.4(4) . . . . ?
C5 N2 B1 F2 65.4(3) . . . . ?
C5 N2 B1 N1 -179.5(2) . . . . ?
C5 C6 C7 C9 -178.7(3) . . . . ?
C5 C6 C7 C8 0.3(5) . . . . ?
C8 C7 C9 Br1 4.0(4) . . . . ?
C8 C7 C9 C10 -177.4(3) . . . . ?
C10 N4 C6 C7 -0.9(3) . . . . ?
C10 N4 C6 C5 177.5(2) . . . . ?
C10 N4 B2 F3 -77.4(3) . . . . ?
C10 N4 B2 O1 49.4(4) . . . . ?
C10 N4 B2 N3 171.0(2) . . . . ?
B2 O1 B2 F3 -90.0(2) 2_655 . . . ?
B2 O1 B2 N3 29.09(15) 2_655 . . . ?
B2 O1 B2 N4 146.6(2) 2_655 . . . ?
B2 N3 C4 N1 -158.7(2) . . . . ?
B2 N3 C4 C4 19.9(5) . . . 2_655 ?
B2 N4 C6 C7 -176.9(2) . . . . ?
B2 N4 C6 C5 1.6(4) . . . . ?
B2 N4 C10 C9 177.6(2) . . . . ?
B2 N4 C10 C11 -1.1(4) . . . . ?
B1 N2 N3 C4 -4.4(3) . . . . ?
B1 N2 N3 B2 156.0(2) . . . . ?
B1 N2 C5 C6 -171.5(3) . . . . ?
B1 N1 C4 N3 2.7(3) . . . . ?
B1 N1 C4 C4 -176.0(3) . . . 2_655 ?
B1 N1 C3 C3 167.3(3) . . . 2_655 ?
B1 N1 C3 C2 -10.9(4) . . . . ?
