#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/47/7234773.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_7234773
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                   11.4844(15)
_cell_length_b                   14.5457(16)
_cell_length_c                   15.7575(19)
_cell_measurement_reflns_used    2294
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.19
_cell_volume                     2632.3(6)
_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 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8309
_diffrn_reflns_theta_full        25.19
_diffrn_reflns_theta_max         25.19
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.980
_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          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.2(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         4545
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0407
_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)+(0.0369P)²+0.5201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.1049
_reflns_number_gt                3285
_reflns_number_total             4545
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-4668.cif
_cod_data_source_block           mo_20151112a_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               7234773
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
C21 C -0.0359(2) 0.16750(19) 0.32801(15) 0.0414(6) Uani 1 1 d . . .
C25 C 0.1453(3) 0.13069(19) 0.40041(16) 0.0448(7) Uani 1 1 d . . .
H25 H 0.2230 0.1127 0.3992 0.054 Uiso 1 1 calc R . .
C26 C 0.0821(3) 0.14363(19) 0.32628(16) 0.0447(7) Uani 1 1 d . . .
C10 C 0.0565(3) 0.19157(19) 0.12403(16) 0.0440(7) Uani 1 1 d . . .
C9 C 0.0565(3) 0.2627(2) 0.06102(17) 0.0490(8) Uani 1 1 d . . .
C12 C -0.0355(3) 0.04512(19) 0.06235(17) 0.0451(7) Uani 1 1 d . . .
C11 C -0.0289(3) 0.1152(2) 0.12599(16) 0.0443(7) Uani 1 1 d . . .
C24 C 0.0870(3) 0.14589(18) 0.47669(16) 0.0404(7) Uani 1 1 d . . .
C23 C -0.0275(3) 0.17482(19) 0.47782(16) 0.0427(7) Uani 1 1 d . . .
C17 C -0.1158(3) -0.02846(19) 0.07371(18) 0.0483(8) Uani 1 1 d . . .
C22 C -0.0916(3) 0.18466(19) 0.40428(16) 0.0461(7) Uani 1 1 d . . .
H22 H -0.1695 0.2022 0.4059 0.055 Uiso 1 1 calc R . .
C7 C -0.0259(3) 0.3342(2) -0.0644(2) 0.0660(9) Uani 1 1 d . . .
H7 H -0.0801 0.3345 -0.1082 0.079 Uiso 1 1 calc R . .
C3 C 0.2197(3) 0.3352(2) 0.1345(2) 0.0638(9) Uani 1 1 d . . .
H3 H 0.2746 0.3820 0.1377 0.077 Uiso 1 1 calc R . .
C1 C 0.1346(3) 0.1982(2) 0.18912(17) 0.0464(7) Uani 1 1 d . . .
C19 C -0.1784(3) 0.0359(2) 0.20779(19) 0.0555(8) Uani 1 1 d . . .
H19 H -0.2250 0.0339 0.2560 0.067 Uiso 1 1 calc R . .
C4 C 0.1389(3) 0.3348(2) 0.06657(19) 0.0566(8) Uani 1 1 d . . .
C20 C -0.1005(3) 0.1085(2) 0.19526(17) 0.0444(7) Uani 1 1 d . . .
C15 C -0.0582(4) -0.0913(2) -0.0608(2) 0.0654(10) Uani 1 1 d . . .
H15 H -0.0673 -0.1353 -0.1031 0.078 Uiso 1 1 calc R . .
C8 C -0.0267(3) 0.2653(2) -0.00667(17) 0.0530(8) Uani 1 1 d . . .
H8 H -0.0822 0.2189 -0.0110 0.064 Uiso 1 1 calc R . .
C14 C 0.0238(3) -0.0209(2) -0.0715(2) 0.0625(9) Uani 1 1 d . . .
H14 H 0.0698 -0.0189 -0.1200 0.075 Uiso 1 1 calc R . .
C6 C 0.0559(4) 0.4049(3) -0.0584(2) 0.0795(12) Uani 1 1 d . . .
H6 H 0.0549 0.4523 -0.0980 0.095 Uiso 1 1 calc R . .
C16 C -0.1243(3) -0.0964(2) 0.0098(2) 0.0608(9) Uani 1 1 d . . .
H16 H -0.1759 -0.1451 0.0166 0.073 Uiso 1 1 calc R . .
C2 C 0.2188(3) 0.2687(2) 0.19507(19) 0.0605(9) Uani 1 1 d . . .
H2 H 0.2722 0.2697 0.2394 0.073 Uiso 1 1 calc R . .
C18 C -0.1850(3) -0.0316(2) 0.14843(19) 0.0564(9) Uani 1 1 d . . .
H18 H -0.2356 -0.0807 0.1568 0.068 Uiso 1 1 calc R . .
C13 C 0.0357(3) 0.0445(2) -0.01034(18) 0.0540(8) Uani 1 1 d . . .
H13 H 0.0921 0.0899 -0.0167 0.065 Uiso 1 1 calc R . .
C5 C 0.1379(4) 0.4054(3) 0.0051(2) 0.0759(12) Uani 1 1 d . . .
H5 H 0.1928 0.4523 0.0076 0.091 Uiso 1 1 calc R . .
C28 C 0.1272(3) 0.14162(18) 0.56541(16) 0.0418(7) Uani 1 1 d . . .
C27 C -0.0621(3) 0.19088(19) 0.56769(17) 0.0450(7) Uani 1 1 d . . .
O2 O -0.10047(17) 0.18031(13) 0.25528(11) 0.0496(5) Uani 1 1 d . . .
O1 O 0.13996(17) 0.12760(13) 0.25042(11) 0.0507(5) Uani 1 1 d . . .
O3 O -0.15322(18) 0.21831(15) 0.59585(12) 0.0563(5) Uani 1 1 d . . .
F2 F -0.02898(19) 0.1129(2) 0.75107(13) 0.1059(9) Uani 1 1 d . . .
F1 F 0.0239(2) 0.26172(16) 0.74179(12) 0.0958(8) Uani 1 1 d . . .
B1 B 0.0441(4) 0.1743(3) 0.7129(2) 0.0595(10) Uani 1 1 d . . .
N2 N 0.0370(2) 0.16917(16) 0.61622(13) 0.0426(6) Uani 1 1 d . . .
N1 N 0.1743(2) 0.14733(16) 0.73416(14) 0.0492(6) Uani 1 1 d . . .
N3 N 0.2298(2) 0.11768(17) 0.59024(14) 0.0502(6) Uani 1 1 d . . .
C29 C 0.2539(3) 0.12024(19) 0.67659(18) 0.0477(7) Uani 1 1 d . . .
C31 C 0.3928(4) 0.0989(2) 0.7874(2) 0.0695(10) Uani 1 1 d . . .
H31 H 0.4672 0.0826 0.8052 0.083 Uiso 1 1 calc R . .
C30 C 0.3658(3) 0.0958(2) 0.7030(2) 0.0610(9) Uani 1 1 d . . .
H30 H 0.4214 0.0777 0.6635 0.073 Uiso 1 1 calc R . .
C32 C 0.3120(3) 0.1254(3) 0.8457(2) 0.0650(10) Uani 1 1 d . . .
H32 H 0.3298 0.1260 0.9033 0.078 Uiso 1 1 calc R . .
C33 C 0.2046(3) 0.1508(2) 0.81787(18) 0.0634(9) Uani 1 1 d . . .
H33 H 0.1501 0.1712 0.8572 0.076 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
O2 C21 C22 116.7(2) . .
O2 C21 C26 122.6(2) . .
C22 C21 C26 120.6(2) . .
C26 C25 C24 117.0(3) . .
O1 C26 C25 116.9(2) . .
O1 C26 C21 121.5(2) . .
C25 C26 C21 121.6(2) . .
C1 C10 C9 118.0(3) . .
C1 C10 C11 118.1(2) . .
C9 C10 C11 123.7(3) . .
C4 C9 C8 118.2(3) . .
C4 C9 C10 119.4(3) . .
C8 C9 C10 122.4(3) . .
C13 C12 C17 118.3(3) . .
C13 C12 C11 122.9(3) . .
C17 C12 C11 118.8(3) . .
C20 C11 C12 118.4(3) . .
C20 C11 C10 117.8(2) . .
C12 C11 C10 123.7(2) . .
C23 C24 C25 121.1(3) . .
C23 C24 C28 107.4(2) . .
C25 C24 C28 131.4(3) . .
C22 C23 C24 121.9(3) . .
C22 C23 C27 129.8(3) . .
C24 C23 C27 108.3(2) . .
C16 C17 C18 122.0(3) . .
C16 C17 C12 118.7(3) . .
C18 C17 C12 119.4(3) . .
C23 C22 C21 117.6(3) . .
C8 C7 C6 120.4(3) . .
C2 C3 C4 121.6(3) . .
C10 C1 O1 119.4(3) . .
C10 C1 C2 123.4(3) . .
O1 C1 C2 117.0(3) . .
C18 C19 C20 119.0(3) . .
C5 C4 C3 121.5(3) . .
C5 C4 C9 119.4(3) . .
C3 C4 C9 119.1(3) . .
C11 C20 C19 123.4(3) . .
C11 C20 O2 118.8(3) . .
C19 C20 O2 117.7(3) . .
C16 C15 C14 121.1(3) . .
C7 C8 C9 121.0(3) . .
C13 C14 C15 119.6(3) . .
C5 C6 C7 120.9(3) . .
C15 C16 C17 120.7(3) . .
C3 C2 C1 118.4(3) . .
C19 C18 C17 121.1(3) . .
C14 C13 C12 121.5(3) . .
C6 C5 C4 120.2(3) . .
N3 C28 N2 126.4(2) . .
N3 C28 C24 125.9(2) . .
N2 C28 C24 107.8(2) . .
O3 C27 N2 125.2(3) . .
O3 C27 C23 129.4(3) . .
N2 C27 C23 105.4(2) . .
C21 O2 C20 117.3(2) . .
C26 O1 C1 116.5(2) . .
F2 B1 F1 110.9(3) . .
F2 B1 N2 112.0(3) . .
F1 B1 N2 111.6(3) . .
F2 B1 N1 109.0(3) . .
F1 B1 N1 108.6(3) . .
N2 B1 N1 104.4(3) . .
C28 N2 C27 111.1(2) . .
C28 N2 B1 123.9(3) . .
C27 N2 B1 125.0(3) . .
C29 N1 C33 119.3(3) . .
C29 N1 B1 124.8(2) . .
C33 N1 B1 115.9(3) . .
C28 N3 C29 118.2(3) . .
N1 C29 N3 122.2(3) . .
N1 C29 C30 119.9(3) . .
N3 C29 C30 118.0(3) . .
C32 C31 C30 120.8(3) . .
C31 C30 C29 119.4(3) . .
C33 C32 C31 118.5(3) . .
C32 C33 N1 122.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C21 O2 1.377(3) .
C21 C22 1.384(4) .
C21 C26 1.400(4) .
C25 C26 1.388(4) .
C25 C24 1.394(4) .
C26 O1 1.387(3) .
C10 C1 1.366(4) .
C10 C9 1.434(4) .
C10 C11 1.482(4) .
C9 C4 1.417(4) .
C9 C8 1.433(4) .
C12 C13 1.407(4) .
C12 C17 1.424(4) .
C12 C11 1.432(4) .
C11 C20 1.370(4) .
C24 C23 1.381(4) .
C24 C28 1.474(4) .
C23 C22 1.381(4) .
C23 C27 1.489(4) .
C17 C16 1.414(4) .
C17 C18 1.421(4) .
C7 C8 1.354(4) .
C7 C6 1.395(5) .
C3 C2 1.358(5) .
C3 C4 1.416(5) .
C1 O1 1.411(3) .
C1 C2 1.412(4) .
C19 C18 1.358(4) .
C19 C20 1.399(4) .
C4 C5 1.411(5) .
C20 O2 1.409(3) .
C15 C16 1.349(5) .
C15 C14 1.402(5) .
C14 C13 1.361(4) .
C6 C5 1.374(6) .
C28 N3 1.289(4) .
C28 N2 1.369(4) .
C27 O3 1.205(3) .
C27 N2 1.407(4) .
F2 B1 1.365(5) .
F1 B1 1.370(5) .
B1 N2 1.527(4) .
B1 N1 1.583(5) .
N1 C29 1.347(4) .
N1 C33 1.365(4) .
N3 C29 1.389(3) .
C29 C30 1.396(4) .
C31 C32 1.362(5) .
C31 C30 1.366(4) .
C32 C33 1.360(5) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339071
