#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/01/7120193.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_7120193
loop_
_publ_author_name
'Zhou, Zhikuan'
'Zhou, Jianping'
'Gai, Lizhi'
'Yuan, Aihua'
'Shen, Zhen'
_publ_section_title
;
 Naphtho[b]-fused BODIPYs: one pot Suzuki-Miyaura-Knoevenagel synthesis
 and photophysical properties
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC02918G
_journal_year                    2017
_chemical_formula_sum            'C33 H23 B F2 N2'
_chemical_formula_weight         496.34
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-03-08 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.057(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.140(5)
_cell_length_b                   14.391(4)
_cell_length_c                   21.159(6)
_cell_measurement_reflns_used    6538
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.58
_cell_volume                     4788(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            22503
_diffrn_reflns_theta_full        27.69
_diffrn_reflns_theta_max         27.69
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_correction_T_min  0.9821
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5564
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.1345
_refine_ls_R_factor_gt           0.0878
_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)+(0.1200P)²+6.4916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2144
_refine_ls_wR_factor_ref         0.2539
_reflns_number_gt                3792
_reflns_number_total             5564
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc02918g2.cif
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        4787(2)
_cod_original_sg_symbol_H-M      'C2/c '
_cod_database_code               7120193
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F 0.15894(15) 0.38438(14) 0.37353(9) 0.0546(6) Uani 1 1 d .
F2 F 0.27899(13) 0.40426(15) 0.33936(12) 0.0612(7) Uani 1 1 d .
N1 N 0.20227(16) 0.26142(18) 0.31172(12) 0.0325(6) Uani 1 1 d .
N2 N 0.14658(16) 0.40804(18) 0.25998(12) 0.0332(6) Uani 1 1 d .
C1 C 0.11296(18) 0.2624(2) 0.20292(14) 0.0296(6) Uani 1 1 d .
C15 C 0.23443(19) 0.1979(2) 0.35806(15) 0.0335(7) Uani 1 1 d .
C5 C 0.08168(18) 0.5128(2) 0.18444(15) 0.0315(7) Uani 1 1 d .
C2 C 0.10997(18) 0.3598(2) 0.20333(14) 0.0306(7) Uani 1 1 d .
C27 C 0.15504(18) 0.2129(2) 0.25844(14) 0.0306(7) Uani 1 1 d .
C6 C 0.0550(2) 0.6057(2) 0.16280(16) 0.0346(7) Uani 1 1 d .
C14 C 0.12956(19) 0.4991(2) 0.24848(15) 0.0326(7) Uani 1 1 d .
C3 C 0.07140(18) 0.4253(2) 0.15458(15) 0.0315(7) Uani 1 1 d .
C12 C 0.1335(2) 0.6598(2) 0.27042(17) 0.0450(8) Uani 1 1 d .
H12 H 0.1514 0.7097 0.2981 0.054 Uiso 1 1 calc R
C24 C 0.20832(19) 0.1072(2) 0.33645(15) 0.0330(7) Uani 1 1 d .
C17 C 0.3016(2) 0.1443(2) 0.46285(17) 0.0422(8) Uani 1 1 d .
H17 H 0.3325 0.1557 0.5048 0.051 Uiso 1 1 calc R
C23 C 0.23124(19) 0.0301(2) 0.38066(16) 0.0346(7) Uani 1 1 d .
C28 C 0.07023(19) 0.2106(2) 0.14378(14) 0.0305(7) Uani 1 1 d .
C16 C 0.28327(19) 0.2166(2) 0.42123(16) 0.0383(8) Uani 1 1 d .
H16 H 0.3021 0.2763 0.4336 0.046 Uiso 1 1 calc R
C25 C 0.15725(19) 0.1165(2) 0.27342(15) 0.0325(7) Uani 1 1 d .
C13 C 0.1559(2) 0.5737(2) 0.29222(16) 0.0406(8) Uani 1 1 d .
H13 H 0.1874 0.5635 0.3342 0.049 Uiso 1 1 calc R
C33 C 0.1183(2) 0.1638(2) 0.10721(16) 0.0395(8) Uani 1 1 d .
H33 H 0.1773 0.1648 0.1198 0.047 Uiso 1 1 calc R
C22 C 0.2118(2) -0.0637(2) 0.36499(19) 0.0460(9) Uani 1 1 d .
H22 H 0.1856 -0.0798 0.3226 0.055 Uiso 1 1 calc R
C19 C 0.2928(2) -0.0206(3) 0.49138(18) 0.0463(9) Uani 1 1 d .
H19 H 0.3200 -0.0066 0.5339 0.056 Uiso 1 1 calc R
C18 C 0.27533(19) 0.0509(2) 0.44510(16) 0.0373(7) Uani 1 1 d .
C11 C 0.0835(2) 0.6789(2) 0.20677(17) 0.0398(8) Uani 1 1 d .
C7 C 0.0017(2) 0.6281(3) 0.10269(17) 0.0453(8) Uani 1 1 d .
H7 H -0.0188 0.5807 0.0735 0.054 Uiso 1 1 calc R
B1 B 0.1993(2) 0.3669(2) 0.32305(17) 0.0348(8) Uani 1 1 d .
C29 C -0.0175(2) 0.2077(2) 0.12435(16) 0.0381(7) Uani 1 1 d .
H29 H -0.0504 0.2388 0.1485 0.046 Uiso 1 1 calc R
C32 C 0.0787(3) 0.1158(3) 0.05221(18) 0.0498(9) Uani 1 1 d .
H32 H 0.1112 0.0846 0.0278 0.060 Uiso 1 1 calc R
C4 C 0.0337(2) 0.4074(2) 0.08445(15) 0.0420(8) Uani 1 1 d .
H4A H -0.0271 0.4053 0.0774 0.063 Uiso 1 1 calc R
H4B H 0.0543 0.3492 0.0721 0.063 Uiso 1 1 calc R
H4C H 0.0498 0.4564 0.0588 0.063 Uiso 1 1 calc R
C21 C 0.2310(3) -0.1317(3) 0.4115(2) 0.0553(10) Uani 1 1 d .
H21 H 0.2172 -0.1931 0.4002 0.066 Uiso 1 1 calc R
C26 C 0.1085(2) 0.0396(2) 0.23404(17) 0.0438(8) Uani 1 1 d .
H26A H 0.0626 0.0655 0.2018 0.066 Uiso 1 1 calc R
H26B H 0.0859 -0.0010 0.2619 0.066 Uiso 1 1 calc R
H26C H 0.1456 0.0052 0.2131 0.066 Uiso 1 1 calc R
C10 C 0.0600(3) 0.7707(2) 0.1880(2) 0.0527(10) Uani 1 1 d .
H10 H 0.0796 0.8191 0.2165 0.063 Uiso 1 1 calc R
C30 C -0.0566(2) 0.1593(2) 0.06960(17) 0.0436(8) Uani 1 1 d .
H30 H -0.1156 0.1573 0.0571 0.052 Uiso 1 1 calc R
C31 C -0.0083(2) 0.1137(2) 0.03334(17) 0.0476(9) Uani 1 1 d .
H31 H -0.0347 0.0816 -0.0039 0.057 Uiso 1 1 calc R
C8 C -0.0208(3) 0.7180(3) 0.0860(2) 0.0565(10) Uani 1 1 d .
H8 H -0.0561 0.7309 0.0458 0.068 Uiso 1 1 calc R
C20 C 0.2705(2) -0.1104(3) 0.4749(2) 0.0541(10) Uani 1 1 d .
H20 H 0.2819 -0.1570 0.5061 0.065 Uiso 1 1 calc R
C9 C 0.0089(3) 0.7901(3) 0.1288(2) 0.0598(11) Uani 1 1 d .
H9 H -0.0059 0.8512 0.1171 0.072 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'
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
C15 N1 C27 107.3(2)
C15 N1 B1 124.9(3)
C27 N1 B1 126.0(2)
C14 N2 C2 107.4(2)
C14 N2 B1 125.7(3)
C2 N2 B1 126.9(3)
C2 C1 C27 120.7(3)
C2 C1 C28 119.8(3)
C27 C1 C28 119.5(3)
N1 C15 C24 110.5(3)
N1 C15 C16 126.6(3)
C24 C15 C16 122.8(3)
C3 C5 C14 106.8(3)
C3 C5 C6 133.7(3)
C14 C5 C6 119.4(3)
N2 C2 C1 119.6(3)
N2 C2 C3 108.8(3)
C1 C2 C3 131.5(3)
N1 C27 C1 119.5(3)
N1 C27 C25 109.0(3)
C1 C27 C25 131.4(3)
C7 C6 C11 117.9(3)
C7 C6 C5 125.2(3)
C11 C6 C5 116.9(3)
N2 C14 C5 110.7(3)
N2 C14 C13 126.8(3)
C5 C14 C13 122.5(3)
C5 C3 C2 106.2(3)
C5 C3 C4 125.6(3)
C2 C3 C4 128.0(3)
C13 C12 C11 123.4(3)
C25 C24 C15 106.7(3)
C25 C24 C23 134.1(3)
C15 C24 C23 119.0(3)
C16 C17 C18 122.9(3)
C22 C23 C18 117.7(3)
C22 C23 C24 125.0(3)
C18 C23 C24 117.3(3)
C29 C28 C33 118.9(3)
C29 C28 C1 121.0(3)
C33 C28 C1 120.1(3)
C17 C16 C15 117.6(3)
C24 C25 C27 106.5(3)
C24 C25 C26 125.4(3)
C27 C25 C26 127.8(3)
C12 C13 C14 117.2(3)
C32 C33 C28 120.2(3)
C21 C22 C23 120.8(3)
C20 C19 C18 121.0(4)
C19 C18 C23 119.6(3)
C19 C18 C17 120.2(3)
C23 C18 C17 120.2(3)
C10 C11 C6 119.1(3)
C10 C11 C12 120.4(3)
C6 C11 C12 120.5(3)
C8 C7 C6 121.6(3)
F2 B1 F1 108.2(3)
F2 B1 N2 112.0(3)
F1 B1 N2 109.6(3)
F2 B1 N1 111.5(3)
F1 B1 N1 109.5(3)
N2 B1 N1 106.1(2)
C30 C29 C28 120.6(3)
C31 C32 C33 120.3(3)
C22 C21 C20 121.2(4)
C9 C10 C11 121.4(4)
C31 C30 C29 120.0(3)
C32 C31 C30 120.0(3)
C7 C8 C9 120.4(4)
C19 C20 C21 119.7(4)
C10 C9 C8 119.5(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 B1 1.393(4)
F2 B1 1.365(4)
N1 C15 1.355(4)
N1 C27 1.397(4)
N1 B1 1.539(4)
N2 C14 1.350(4)
N2 C2 1.395(4)
N2 B1 1.530(4)
C1 C2 1.404(4)
C1 C27 1.410(4)
C1 C28 1.486(4)
C15 C24 1.415(4)
C15 C16 1.415(4)
C5 C3 1.403(4)
C5 C14 1.414(4)
C5 C6 1.446(4)
C2 C3 1.431(4)
C27 C25 1.422(4)
C6 C7 1.402(5)
C6 C11 1.412(5)
C14 C13 1.419(4)
C3 C4 1.493(4)
C12 C13 1.343(5)
C12 C11 1.432(5)
C24 C25 1.407(4)
C24 C23 1.445(4)
C17 C16 1.351(5)
C17 C18 1.434(5)
C23 C22 1.408(5)
C23 C18 1.420(5)
C28 C29 1.384(4)
C28 C33 1.387(4)
C25 C26 1.497(4)
C33 C32 1.380(5)
C22 C21 1.373(5)
C19 C20 1.365(5)
C19 C18 1.404(5)
C11 C10 1.406(5)
C7 C8 1.368(5)
C29 C30 1.377(5)
C32 C31 1.370(5)
C21 C20 1.383(6)
C10 C9 1.363(6)
C30 C31 1.377(5)
C8 C9 1.389(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139187757
