#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:02:58 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/04/1520445.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_1520445
loop_
_publ_author_name
'Maeda, Chihiro'
'Todaka, Takumi'
'Ema, Tadashi'
_publ_section_title
;
 Carbazole-Based Boron Dipyrromethenes (BODIPYs): Facile Synthesis,
 Structures, and Fine-Tunable Optical Properties.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3090
_journal_page_last               3093
_journal_paper_doi               10.1021/acs.orglett.5b01363
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C23 H18 B F2 N3'
_chemical_formula_sum            'C23 H18 B F2 N3'
_chemical_formula_weight         385.21
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.795(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.594(2)
_cell_length_b                   8.7428(17)
_cell_length_c                   21.526(6)
_cell_measurement_reflns_used    1805
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      25.3
_cell_volume                     1773.6(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17445
_diffrn_reflns_theta_full        66.00
_diffrn_reflns_theta_max         66.00
_diffrn_reflns_theta_min         6.57
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_T_max  0.9298
_exptl_absorpt_correction_T_min  0.7910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3076
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0554P)²+0.5569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0876
_reflns_number_gt                2916
_reflns_number_total             3076
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01363_si_002.cif
_cod_data_source_block           40705c2
_cod_depositor_comments
'Adding full bibliography for 1520439--1520445.cif.'
_cod_original_cell_volume        1773.5(7)
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_database_code               1520445
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.93383(7) 0.20584(7) 0.10466(3) 0.02186(18) Uani 1 1 d .
F2 F 0.87201(6) 0.42399(8) 0.05006(3) 0.02192(18) Uani 1 1 d .
C10 C 1.40584(12) 0.55779(13) 0.15362(6) 0.0209(3) Uani 1 1 d .
H1 H 1.4813 0.5514 0.1308 0.025 Uiso 1 1 calc R
N1 N 1.03556(10) 0.44117(11) 0.14999(4) 0.0178(2) Uani 1 1 d .
N2 N 1.11367(10) 0.32854(10) 0.05592(4) 0.0174(2) Uani 1 1 d .
N3 N 0.93543(10) 0.12914(11) -0.08628(4) 0.0187(2) Uani 1 1 d .
C11 C 1.27746(12) 0.48224(13) 0.13050(5) 0.0186(2) Uani 1 1 d .
C21 C 0.97809(12) 0.18009(12) -0.02823(5) 0.0181(2) Uani 1 1 d .
H2 H 0.9086 0.1755 -0.0021 0.022 Uiso 1 1 calc R
C16 C 1.10901(12) 0.23977(12) 0.00112(5) 0.0179(2) Uani 1 1 d .
C14 C 1.33678(12) 0.32451(13) 0.03516(5) 0.0188(2) Uani 1 1 d .
C12 C 1.17008(12) 0.50094(12) 0.16594(5) 0.0177(2) Uani 1 1 d .
C8 C 1.31854(12) 0.65228(13) 0.24572(6) 0.0215(3) Uani 1 1 d .
H3 H 1.3342 0.7074 0.2844 0.026 Uiso 1 1 calc R
C7 C 1.18881(12) 0.57980(12) 0.22388(5) 0.0191(2) Uani 1 1 d .
C17 C 1.48428(12) 0.33475(13) 0.03746(6) 0.0220(3) Uani 1 1 d .
H4 H 1.5417 0.3972 0.0682 0.026 Uiso 1 1 calc R
C19 C 1.45951(13) 0.15721(15) -0.04979(6) 0.0277(3) Uani 1 1 d .
H5 H 1.5030 0.1002 -0.0785 0.033 Uiso 1 1 calc R
C9 C 1.42439(12) 0.64215(13) 0.20966(6) 0.0226(3) Uani 1 1 d .
H6 H 1.5117 0.6941 0.2235 0.027 Uiso 1 1 calc R
C1 C 0.96455(12) 0.47980(13) 0.19871(5) 0.0186(2) Uani 1 1 d .
C2 C 0.82567(12) 0.44412(14) 0.20445(6) 0.0219(3) Uani 1 1 d .
H7 H 0.7650 0.3878 0.1726 0.026 Uiso 1 1 calc R
C18 C 1.54378(13) 0.25306(15) -0.00547(6) 0.0264(3) Uani 1 1 d .
H8 H 1.6426 0.2614 -0.0052 0.032 Uiso 1 1 calc R
C4 C 0.86729(13) 0.57967(14) 0.30483(6) 0.0247(3) Uani 1 1 d .
H9 H 0.8323 0.6130 0.3410 0.030 Uiso 1 1 calc R
C13 C 1.24624(11) 0.38455(13) 0.07517(5) 0.0176(2) Uani 1 1 d .
C15 C 1.25075(12) 0.23238(13) -0.01109(5) 0.0192(2) Uani 1 1 d .
C22 C 0.79664(12) 0.05654(14) -0.10414(6) 0.0225(3) Uani 1 1 d .
H10 H 0.7523 0.0476 -0.0668 0.034 Uiso 1 1 calc R
H11 H 0.8082 -0.0455 -0.1213 0.034 Uiso 1 1 calc R
H12 H 0.7363 0.1188 -0.1363 0.034 Uiso 1 1 calc R
C20 C 1.31593(13) 0.14403(14) -0.05253(6) 0.0240(3) Uani 1 1 d .
H13 H 1.2611 0.0763 -0.0819 0.029 Uiso 1 1 calc R
C5 C 1.00463(13) 0.61663(13) 0.29881(6) 0.0226(3) Uani 1 1 d .
H14 H 1.0635 0.6760 0.3302 0.027 Uiso 1 1 calc R
C6 C 1.05508(12) 0.56498(13) 0.24559(5) 0.0195(3) Uani 1 1 d .
C3 C 0.77936(12) 0.49376(14) 0.25824(6) 0.0244(3) Uani 1 1 d .
H15 H 0.6860 0.4690 0.2637 0.029 Uiso 1 1 calc R
C23 C 1.01252(12) 0.14689(14) -0.13817(5) 0.0220(3) Uani 1 1 d .
H16 H 1.0814 0.2303 -0.1284 0.033 Uiso 1 1 calc R
H17 H 0.9455 0.1707 -0.1772 0.033 Uiso 1 1 calc R
H18 H 1.0625 0.0516 -0.1438 0.033 Uiso 1 1 calc R
B1 B 0.98200(13) 0.35132(14) 0.09000(6) 0.0174(3) 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 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
C9 C10 C11 121.07(11)
C12 N1 C1 106.73(9)
C12 N1 B1 124.19(9)
C1 N1 B1 129.07(9)
C13 N2 C16 109.69(9)
C13 N2 B1 126.62(10)
C16 N2 B1 123.64(9)
C21 N3 C23 125.33(10)
C21 N3 C22 120.18(9)
C23 N3 C22 114.37(9)
C12 C11 C10 115.94(11)
C12 C11 C13 117.12(10)
C10 C11 C13 126.91(10)
N3 C21 C16 130.42(11)
C21 C16 N2 118.05(10)
C21 C16 C15 134.70(11)
N2 C16 C15 107.25(9)
C17 C14 C15 120.58(11)
C17 C14 C13 132.34(11)
C15 C14 C13 106.94(10)
N1 C12 C11 124.81(11)
N1 C12 C7 111.46(10)
C11 C12 C7 123.70(11)
C9 C8 C7 118.71(11)
C8 C7 C12 118.58(11)
C8 C7 C6 135.86(11)
C12 C7 C6 105.53(10)
C18 C17 C14 118.97(11)
C20 C19 C18 121.61(12)
C8 C9 C10 121.81(11)
N1 C1 C2 128.39(11)
N1 C1 C6 110.05(10)
C2 C1 C6 121.55(11)
C3 C2 C1 117.70(11)
C17 C18 C19 120.51(11)
C5 C4 C3 120.88(11)
N2 C13 C14 108.92(10)
N2 C13 C11 120.14(10)
C14 C13 C11 130.86(10)
C20 C15 C14 119.07(11)
C20 C15 C16 133.48(11)
C14 C15 C16 107.02(10)
C19 C20 C15 119.13(11)
C4 C5 C6 118.81(11)
C5 C6 C1 119.59(11)
C5 C6 C7 134.19(11)
C1 C6 C7 106.22(10)
C2 C3 C4 121.45(11)
F2 B1 F1 108.03(9)
F2 B1 N1 112.85(9)
F1 B1 N1 110.47(10)
F2 B1 N2 110.52(10)
F1 B1 N2 108.24(9)
N1 B1 N2 106.64(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 B1 1.4091(14)
F2 B1 1.3843(14)
C10 C9 1.3966(17)
C10 C11 1.4041(16)
N1 C12 1.3749(15)
N1 C1 1.3948(15)
N1 B1 1.5166(16)
N2 C13 1.3534(14)
N2 C16 1.4058(15)
N2 B1 1.5876(16)
N3 C21 1.3174(15)
N3 C23 1.4588(15)
N3 C22 1.4601(15)
C11 C12 1.4017(16)
C11 C13 1.4505(16)
C21 C16 1.3970(16)
C16 C15 1.4339(16)
C14 C17 1.4096(16)
C14 C15 1.4190(16)
C14 C13 1.4323(16)
C12 C7 1.4068(17)
C8 C9 1.3917(18)
C8 C7 1.3973(17)
C7 C6 1.4510(17)
C17 C18 1.3737(18)
C19 C20 1.3725(18)
C19 C18 1.4061(18)
C1 C2 1.3962(16)
C1 C6 1.4139(17)
C2 C3 1.3852(18)
C4 C5 1.3861(18)
C4 C3 1.4016(18)
C15 C20 1.4114(17)
C5 C6 1.3995(17)
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
C9 C10 C11 C12 1.79(16)
C9 C10 C11 C13 -176.45(11)
C23 N3 C21 C16 -10.72(19)
C22 N3 C21 C16 173.44(11)
N3 C21 C16 N2 160.43(11)
N3 C21 C16 C15 -20.0(2)
C13 N2 C16 C21 -175.97(10)
B1 N2 C16 C21 6.16(15)
C13 N2 C16 C15 4.37(12)
B1 N2 C16 C15 -173.50(9)
C1 N1 C12 C11 177.32(10)
B1 N1 C12 C11 -2.62(17)
C1 N1 C12 C7 -0.68(12)
B1 N1 C12 C7 179.38(10)
C10 C11 C12 N1 177.49(10)
C13 C11 C12 N1 -4.09(16)
C10 C11 C12 C7 -4.74(16)
C13 C11 C12 C7 173.69(10)
C9 C8 C7 C12 -0.69(16)
C9 C8 C7 C6 -178.74(12)
N1 C12 C7 C8 -177.70(9)
C11 C12 C7 C8 4.27(16)
N1 C12 C7 C6 0.89(12)
C11 C12 C7 C6 -177.14(10)
C15 C14 C17 C18 -0.55(17)
C13 C14 C17 C18 174.60(12)
C7 C8 C9 C10 -2.10(17)
C11 C10 C9 C8 1.53(18)
C12 N1 C1 C2 -179.51(11)
B1 N1 C1 C2 0.42(19)
C12 N1 C1 C6 0.18(12)
B1 N1 C1 C6 -179.88(10)
N1 C1 C2 C3 179.00(11)
C6 C1 C2 C3 -0.66(17)
C14 C17 C18 C19 -1.87(18)
C20 C19 C18 C17 1.2(2)
C16 N2 C13 C14 -3.93(12)
B1 N2 C13 C14 173.87(10)
C16 N2 C13 C11 179.01(9)
B1 N2 C13 C11 -3.19(16)
C17 C14 C13 N2 -173.72(12)
C15 C14 C13 N2 1.91(12)
C17 C14 C13 C11 2.9(2)
C15 C14 C13 C11 178.55(11)
C12 C11 C13 N2 6.75(15)
C10 C11 C13 N2 -175.02(10)
C12 C11 C13 C14 -169.58(11)
C10 C11 C13 C14 8.7(2)
C17 C14 C15 C20 3.63(17)
C13 C14 C15 C20 -172.62(10)
C17 C14 C15 C16 177.03(10)
C13 C14 C15 C16 0.77(12)
C21 C16 C15 C20 -10.6(2)
N2 C16 C15 C20 168.96(12)
C21 C16 C15 C14 177.35(12)
N2 C16 C15 C14 -3.07(12)
C18 C19 C20 C15 1.9(2)
C14 C15 C20 C19 -4.27(17)
C16 C15 C20 C19 -175.56(12)
C3 C4 C5 C6 -0.79(17)
C4 C5 C6 C1 1.43(16)
C4 C5 C6 C7 -179.63(12)
N1 C1 C6 C5 179.56(10)
C2 C1 C6 C5 -0.72(17)
N1 C1 C6 C7 0.35(12)
C2 C1 C6 C7 -179.93(10)
C8 C7 C6 C5 -1.6(2)
C12 C7 C6 C5 -179.77(12)
C8 C7 C6 C1 177.49(12)
C12 C7 C6 C1 -0.73(12)
C1 C2 C3 C4 1.33(17)
C5 C4 C3 C2 -0.63(18)
C12 N1 B1 F2 -115.91(11)
C1 N1 B1 F2 64.16(15)
C12 N1 B1 F1 123.03(10)
C1 N1 B1 F1 -56.90(15)
C12 N1 B1 N2 5.62(14)
C1 N1 B1 N2 -174.30(10)
C13 N2 B1 F2 120.21(11)
C16 N2 B1 F2 -62.28(13)
C13 N2 B1 F1 -121.66(11)
C16 N2 B1 F1 55.85(13)
C13 N2 B1 N1 -2.79(15)
C16 N2 B1 N1 174.72(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139045559
