#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/47/7234772.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_7234772
loop_
_publ_author_name
'Yanping Wu'
'Sisi Wang'
'Zhifang Li'
'Zhen Shen'
'Hua Lu'
_publ_section_title
;
 Chiral binaphthyl-linked BODIPY analogues: synthesis and spectroscopic
 properties
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              4668
_journal_page_last               4674
_journal_paper_doi               10.1039/C6TC00975A
_journal_volume                  4
_journal_year                    2016
_chemical_formula_sum            'C33 H18 B F2 N3 O3'
_chemical_formula_weight         553.31
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4915(12)
_cell_length_b                   14.5392(16)
_cell_length_c                   15.7532(17)
_cell_measurement_reflns_used    2295
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.19
_cell_volume                     2632.0(5)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8376
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         4687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0415P)²+0.1455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0918
_reflns_number_gt                3513
_reflns_number_total             4687
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-4668.cif
_cod_data_source_block           mo_20151111a_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7234772
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C 0.4709(2) 0.61501(17) 0.37412(15) 0.0452(6) Uani 1 1 d . . .
C7 C 0.4745(3) 0.83480(18) 0.56489(18) 0.0654(7) Uani 1 1 d . . .
H7 H 0.4200 0.8353 0.6085 0.078 Uiso 1 1 calc R . .
C12 C 0.4643(2) 0.54483(15) 0.43791(15) 0.0454(6) Uani 1 1 d . . .
C3 C 0.7198(2) 0.8345(2) 0.36584(18) 0.0641(8) Uani 1 1 d . . .
H3 H 0.7760 0.8804 0.3632 0.077 Uiso 1 1 calc R . .
C9 C 0.5561(2) 0.76266(16) 0.43935(15) 0.0462(6) Uani 1 1 d . . .
C8 C 0.4747(2) 0.76509(18) 0.50614(15) 0.0533(6) Uani 1 1 d . . .
H8 H 0.4198 0.7183 0.5105 0.064 Uiso 1 1 calc R . .
C10 C 0.5566(2) 0.69190(16) 0.37610(14) 0.0442(6) Uani 1 1 d . . .
C17 C 0.3835(2) 0.47137(15) 0.42612(16) 0.0475(6) Uani 1 1 d . . .
C2 C 0.7180(2) 0.7685(2) 0.30441(17) 0.0570(7) Uani 1 1 d . . .
H2 H 0.7703 0.7703 0.2594 0.068 Uiso 1 1 calc R . .
C4 C 0.6390(2) 0.83521(17) 0.43331(16) 0.0556(7) Uani 1 1 d . . .
C19 C 0.3215(2) 0.53576(19) 0.29241(16) 0.0556(7) Uani 1 1 d . . .
H19 H 0.2749 0.5336 0.2442 0.067 Uiso 1 1 calc R . .
C16 C 0.3757(3) 0.40326(18) 0.4897(2) 0.0613(8) Uani 1 1 d . . .
H16 H 0.3251 0.3539 0.4825 0.074 Uiso 1 1 calc R . .
C1 C 0.6355(2) 0.69796(17) 0.31073(15) 0.0462(6) Uani 1 1 d . . .
C5 C 0.6362(3) 0.9064(2) 0.4949(2) 0.0753(9) Uani 1 1 d . . .
H5 H 0.6893 0.9546 0.4916 0.090 Uiso 1 1 calc R . .
C14 C 0.5235(3) 0.47888(17) 0.57143(18) 0.0629(7) Uani 1 1 d . . .
H14 H 0.5699 0.4806 0.6198 0.075 Uiso 1 1 calc R . .
C18 C 0.3145(2) 0.46837(19) 0.35168(17) 0.0591(7) Uani 1 1 d . . .
H18 H 0.2637 0.4194 0.3433 0.071 Uiso 1 1 calc R . .
C15 C 0.4413(3) 0.40892(18) 0.5614(2) 0.0649(8) Uani 1 1 d . . .
H15 H 0.4314 0.3656 0.6042 0.078 Uiso 1 1 calc R . .
C20 C 0.3993(2) 0.60857(17) 0.30447(15) 0.0450(6) Uani 1 1 d . . .
C6 C 0.5568(3) 0.9050(2) 0.5586(2) 0.0819(10) Uani 1 1 d . . .
H6 H 0.5573 0.9517 0.5988 0.098 Uiso 1 1 calc R . .
C13 C 0.5358(2) 0.54473(17) 0.51031(16) 0.0543(7) Uani 1 1 d . . .
H13 H 0.5921 0.5901 0.5167 0.065 Uiso 1 1 calc R . .
C21 C 0.4638(2) 0.66710(15) 0.17173(14) 0.0433(5) Uani 1 1 d . . .
C25 C 0.6446(2) 0.63044(15) 0.09956(14) 0.0442(6) Uani 1 1 d . . .
H25 H 0.7221 0.6120 0.1008 0.053 Uiso 1 1 calc R . .
C22 C 0.40871(19) 0.68480(15) 0.09581(14) 0.0440(5) Uani 1 1 d . . .
H22 H 0.3312 0.7031 0.0944 0.053 Uiso 1 1 calc R . .
C23 C 0.4719(2) 0.67469(15) 0.02174(14) 0.0409(5) Uani 1 1 d . . .
C24 C 0.5869(2) 0.64601(15) 0.02311(14) 0.0407(5) Uani 1 1 d . . .
C26 C 0.5821(2) 0.64360(15) 0.17345(14) 0.0432(6) Uani 1 1 d . . .
O1 O 0.63961(13) 0.62738(11) 0.24995(10) 0.0499(4) Uani 1 1 d . . .
O2 O 0.39918(13) 0.68044(11) 0.24500(10) 0.0487(4) Uani 1 1 d . . .
B1 B 0.5434(3) 0.6748(2) -0.21258(19) 0.0584(8) Uani 1 1 d . . .
F2 F 0.47170(14) 0.61278(16) -0.25117(12) 0.1016(7) Uani 1 1 d . . .
F1 F 0.52356(17) 0.76170(13) -0.24151(11) 0.0938(6) Uani 1 1 d . . .
N2 N 0.53672(16) 0.66909(13) -0.11669(11) 0.0425(5) Uani 1 1 d . . .
N1 N 0.67431(17) 0.64702(13) -0.23469(12) 0.0486(5) Uani 1 1 d . . .
O3 O 0.34682(14) 0.71861(12) -0.09554(10) 0.0547(4) Uani 1 1 d . . .
C28 C 0.6270(2) 0.64211(15) -0.06506(15) 0.0427(5) Uani 1 1 d . . .
C27 C 0.4383(2) 0.69120(15) -0.06711(15) 0.0433(6) Uani 1 1 d . . .
N3 N 0.72958(17) 0.61738(14) -0.09016(12) 0.0492(5) Uani 1 1 d . . .
C31 C 0.8940(3) 0.5992(2) -0.2872(2) 0.0661(8) Uani 1 1 d . . .
H31 H 0.9688 0.5839 -0.3048 0.079 Uiso 1 1 calc R . .
C29 C 0.7544(2) 0.62027(16) -0.17652(16) 0.0476(6) Uani 1 1 d . . .
C30 C 0.8652(2) 0.59551(18) -0.20312(18) 0.0599(7) Uani 1 1 d . . .
H30 H 0.9201 0.5763 -0.1635 0.072 Uiso 1 1 calc R . .
C32 C 0.8120(3) 0.6256(2) -0.34539(18) 0.0686(8) Uani 1 1 d . . .
H32 H 0.8296 0.6265 -0.4030 0.082 Uiso 1 1 calc R . .
C33 C 0.7043(2) 0.6506(2) -0.31760(16) 0.0608(7) Uani 1 1 d . . .
H33 H 0.6496 0.6707 -0.3569 0.073 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'
B B 0.0013 0.0007 '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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C20 C11 C12 118.7(2) . .
C20 C11 C10 117.6(2) . .
C12 C11 C10 123.6(2) . .
C8 C7 C6 119.4(3) . .
C13 C12 C17 119.0(2) . .
C13 C12 C11 122.6(2) . .
C17 C12 C11 118.4(2) . .
C2 C3 C4 122.0(2) . .
C8 C9 C4 118.4(2) . .
C8 C9 C10 122.7(2) . .
C4 C9 C10 118.9(2) . .
C7 C8 C9 121.6(3) . .
C1 C10 C9 118.5(2) . .
C1 C10 C11 117.9(2) . .
C9 C10 C11 123.4(2) . .
C16 C17 C18 122.0(2) . .
C16 C17 C12 118.3(2) . .
C18 C17 C12 119.7(2) . .
C3 C2 C1 118.4(2) . .
C3 C4 C5 122.4(3) . .
C3 C4 C9 119.0(2) . .
C5 C4 C9 118.6(3) . .
C18 C19 C20 119.4(3) . .
C15 C16 C17 120.7(3) . .
C10 C1 C2 123.1(2) . .
C10 C1 O1 119.1(2) . .
C2 C1 O1 117.6(2) . .
C6 C5 C4 120.6(3) . .
C13 C14 C15 120.0(3) . .
C19 C18 C17 121.0(2) . .
C16 C15 C14 120.9(3) . .
C11 C20 C19 122.9(2) . .
C11 C20 O2 118.9(2) . .
C19 C20 O2 118.2(2) . .
C5 C6 C7 121.4(3) . .
C14 C13 C12 120.9(3) . .
C22 C21 O2 116.75(19) . .
C22 C21 C26 120.6(2) . .
O2 C21 C26 122.5(2) . .
C26 C25 C24 117.3(2) . .
C21 C22 C23 118.1(2) . .
C22 C23 C24 121.3(2) . .
C22 C23 C27 130.4(2) . .
C24 C23 C27 108.3(2) . .
C23 C24 C25 121.1(2) . .
C23 C24 C28 107.25(19) . .
C25 C24 C28 131.6(2) . .
C25 C26 O1 117.25(19) . .
C25 C26 C21 121.5(2) . .
O1 C26 C21 121.2(2) . .
C26 O1 C1 116.70(17) . .
C21 O2 C20 116.80(17) . .
F1 B1 F2 111.3(3) . .
F1 B1 N2 112.1(2) . .
F2 B1 N2 112.2(3) . .
F1 B1 N1 108.6(3) . .
F2 B1 N1 107.8(2) . .
N2 B1 N1 104.6(2) . .
C28 N2 C27 109.98(18) . .
C28 N2 B1 124.6(2) . .
C27 N2 B1 125.4(2) . .
C33 N1 C29 119.4(2) . .
C33 N1 B1 116.2(2) . .
C29 N1 B1 124.4(2) . .
N3 C28 N2 125.8(2) . .
N3 C28 C24 125.9(2) . .
N2 C28 C24 108.25(19) . .
O3 C27 N2 124.5(2) . .
O3 C27 C23 129.3(2) . .
N2 C27 C23 106.24(19) . .
C28 N3 C29 118.5(2) . .
C30 C31 C32 119.6(3) . .
N1 C29 C30 119.6(2) . .
N1 C29 N3 122.0(2) . .
C30 C29 N3 118.4(2) . .
C31 C30 C29 120.3(3) . .
C33 C32 C31 119.0(3) . .
N1 C33 C32 122.1(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C11 C20 1.374(3) .
C11 C12 1.434(3) .
C11 C10 1.490(3) .
C7 C8 1.373(4) .
C7 C6 1.395(4) .
C12 C13 1.405(4) .
C12 C17 1.427(3) .
C3 C2 1.363(4) .
C3 C4 1.411(4) .
C9 C8 1.408(4) .
C9 C4 1.425(3) .
C9 C10 1.432(3) .
C10 C1 1.375(3) .
C17 C16 1.411(4) .
C17 C18 1.416(4) .
C2 C1 1.401(3) .
C4 C5 1.420(4) .
C19 C18 1.356(4) .
C19 C20 1.399(3) .
C16 C15 1.361(4) .
C1 O1 1.404(3) .
C5 C6 1.355(5) .
C14 C13 1.365(4) .
C14 C15 1.397(4) .
C20 O2 1.403(3) .
C21 C22 1.378(3) .
C21 O2 1.386(3) .
C21 C26 1.401(3) .
C25 C26 1.381(3) .
C25 C24 1.393(3) .
C22 C23 1.382(3) .
C23 C24 1.387(3) .
C23 C27 1.471(3) .
C24 C28 1.464(3) .
C26 O1 1.395(3) .
B1 F1 1.363(4) .
B1 F2 1.364(4) .
B1 N2 1.515(3) .
B1 N1 1.597(4) .
N2 C28 1.375(3) .
N2 C27 1.411(3) .
N1 C33 1.352(3) .
N1 C29 1.356(3) .
O3 C27 1.211(3) .
C28 N3 1.295(3) .
N3 C29 1.391(3) .
C31 C30 1.366(4) .
C31 C32 1.369(4) .
C29 C30 1.388(3) .
C32 C33 1.362(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339071
