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#$Date: 2021-11-29 11:00:52 +0200 (Mon, 29 Nov 2021) $
#$Revision: 270903 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/54/1565411.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_1565411
loop_
_publ_author_name
'Şenkuytu, Elif'
'Okutan, Elif'
'Tanrıverdi Eçik, Esra'
_publ_section_title
;
 Cyclotriphosphazene-BODIPY Dyads: Synthesis, halogen atom effect on the
 photophysical and singlet oxygen generation properties
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119342
_journal_paper_doi               10.1016/j.ica.2019.119342
_journal_volume                  502
_journal_year                    2020
_chemical_formula_moiety         'C23 H24 B Br2 F2 N5 O'
_chemical_formula_sum            'C23 H24 B Br2 F2 N5 O'
_chemical_formula_weight         595.10
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_cell_angle_alpha                93.077(10)
_cell_angle_beta                 97.624(10)
_cell_angle_gamma                105.547(9)
_cell_formula_units_Z            2
_cell_length_a                   9.2039(13)
_cell_length_b                   11.6656(15)
_cell_length_c                   11.9723(16)
_cell_measurement_reflns_used    1812
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.86
_cell_measurement_theta_min      2.32
_cell_volume                     1222.1(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0796
_diffrn_reflns_av_unetI/netI     0.1117
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10580
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.022
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_min         1.724
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.358
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_description       rod
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.619
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       0.0067(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4301
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0556
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0313P)²+0.2700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1406
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2609
_reflns_number_total             4301
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ICA-2020-502-119342.cif
_cod_data_source_block           18gtu332_es_et_br_0m
_cod_database_code               1565411
_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   0.834
_shelx_estimated_absorpt_t_min   0.230
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C2(H2A,H2B), C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C8(H8), C7(H7)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C17(H17A,H17B,
 H17C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_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 0.66953(7) 1.23156(6) 0.64197(5) 0.0649(3) Uani 1 1 d . . . . .
Br2 Br 0.93106(8) 0.51382(6) 0.24124(5) 0.0702(3) Uani 1 1 d . . . . .
F1 F 0.6948(3) 0.9307(3) 0.2429(2) 0.0556(8) Uani 1 1 d . . . . .
F2 F 0.9430(3) 1.0149(3) 0.3076(3) 0.0597(9) Uani 1 1 d . . . . .
O1 O 0.6343(4) 0.4951(3) 0.8775(3) 0.0521(10) Uani 1 1 d . . . . .
N5 N 0.8338(4) 0.8137(4) 0.3475(3) 0.0367(10) Uani 1 1 d . . . . .
N4 N 0.7691(4) 0.9839(4) 0.4428(3) 0.0370(10) Uani 1 1 d . . . . .
C18 C 0.7999(5) 0.7496(4) 0.4397(4) 0.0363(12) Uani 1 1 d . . . . .
C11 C 0.7494(5) 0.8004(4) 0.5308(4) 0.0373(12) Uani 1 1 d . . . . .
C13 C 0.6894(5) 0.9864(5) 0.6154(4) 0.0384(12) Uani 1 1 d . . . . .
C12 C 0.7329(5) 0.9151(5) 0.5329(4) 0.0381(12) Uani 1 1 d . . . . .
C9 C 0.7130(5) 0.7259(4) 0.6263(4) 0.0365(12) Uani 1 1 d . . . . .
C5 C 0.6519(5) 0.5701(4) 0.7929(4) 0.0393(12) Uani 1 1 d . . . . .
C14 C 0.7035(5) 1.0948(5) 0.5723(4) 0.0430(13) Uani 1 1 d . . . . .
C19 C 0.8297(5) 0.6368(5) 0.4217(4) 0.0404(13) Uani 1 1 d . . . . .
C6 C 0.7898(6) 0.6569(5) 0.8037(4) 0.0441(13) Uani 1 1 d . . . . .
H6 H 0.863153 0.662881 0.866777 0.053 Uiso 1 1 calc R . . . .
C10 C 0.8192(5) 0.7341(5) 0.7222(4) 0.0445(13) Uani 1 1 d . . . . .
H10 H 0.911845 0.793025 0.731217 0.053 Uiso 1 1 calc R . . . .
C15 C 0.7520(5) 1.0924(5) 0.4669(4) 0.0416(13) Uani 1 1 d . . . . .
C8 C 0.5750(6) 0.6426(5) 0.6187(4) 0.0495(15) Uani 1 1 d . . . . .
H8 H 0.500813 0.638165 0.556598 0.059 Uiso 1 1 calc R . . . .
C20 C 0.8790(6) 0.6382(5) 0.3174(5) 0.0455(13) Uani 1 1 d . . . . .
C21 C 0.8825(6) 0.7477(5) 0.2733(4) 0.0456(13) Uani 1 1 d . . . . .
C22 C 0.8169(6) 0.5374(5) 0.4963(5) 0.0517(15) Uani 1 1 d . . . . .
H22A H 0.891734 0.563017 0.563130 0.077 Uiso 1 1 calc GR . . . .
H22B H 0.834000 0.469714 0.456499 0.077 Uiso 1 1 calc GR . . . .
H22C H 0.716689 0.515461 0.517370 0.077 Uiso 1 1 calc GR . . . .
C7 C 0.5426(6) 0.5647(5) 0.7009(5) 0.0519(15) Uani 1 1 d . . . . .
H7 H 0.447576 0.508965 0.694081 0.062 Uiso 1 1 calc R . . . .
C16 C 0.7827(6) 1.1907(5) 0.3920(5) 0.0536(15) Uani 1 1 d . . . . .
H16A H 0.884768 1.241164 0.414788 0.080 Uiso 1 1 calc GR . . . .
H16B H 0.711484 1.236884 0.397515 0.080 Uiso 1 1 calc GR . . . .
H16C H 0.771746 1.157595 0.315157 0.080 Uiso 1 1 calc GR . . . .
C3 C 0.5189(6) 0.3220(5) 0.9627(5) 0.0588(16) Uani 1 1 d . . . . .
H3A H 0.526299 0.371854 1.031880 0.071 Uiso 1 1 calc R . . . .
H3B H 0.427605 0.255699 0.957433 0.071 Uiso 1 1 calc R . . . .
C4 C 0.5019(6) 0.3940(5) 0.8639(5) 0.0548(15) Uani 1 1 d . . . . .
H4A H 0.494427 0.345981 0.793499 0.066 Uiso 1 1 calc R . . . .
H4B H 0.410315 0.420324 0.862153 0.066 Uiso 1 1 calc R . . . .
C23 C 0.9301(6) 0.7870(5) 0.1652(5) 0.0603(16) Uani 1 1 d . . . . .
H23A H 0.860826 0.827353 0.129433 0.090 Uiso 1 1 calc GR . . . .
H23B H 0.929003 0.718650 0.116356 0.090 Uiso 1 1 calc GR . . . .
H23C H 1.031325 0.840487 0.179565 0.090 Uiso 1 1 calc GR . . . .
C17 C 0.6417(7) 0.9565(5) 0.7270(4) 0.0590(16) Uani 1 1 d . . . . .
H17A H 0.564723 0.881135 0.717568 0.089 Uiso 1 1 calc GR . . . .
H17B H 0.601430 1.017631 0.756576 0.089 Uiso 1 1 calc GR . . . .
H17C H 0.728375 0.951345 0.778748 0.089 Uiso 1 1 calc GR . . . .
N2 N 0.8096(10) 0.0834(9) 1.0439(6) 0.107(3) Uani 1 1 d . . . . .
B1 B 0.8108(6) 0.9389(5) 0.3313(5) 0.0382(14) Uani 1 1 d . . . . .
C2 C 0.6531(7) 0.2744(6) 0.9703(5) 0.0679(18) Uani 1 1 d . . . . .
H2A H 0.744371 0.339737 0.970986 0.081 Uiso 1 1 calc R . . . .
H2B H 0.642699 0.219602 0.903971 0.081 Uiso 1 1 calc R . . . .
N3 N 0.8157(8) 0.1774(7) 1.0927(6) 0.106(3) Uani 1 1 d . . . . .
C1 C 0.6706(9) 0.2099(7) 1.0757(6) 0.087(2) Uani 1 1 d . . . . .
H1A H 0.665839 0.260732 1.141120 0.104 Uiso 1 1 calc R . . . .
H1B H 0.586354 0.137912 1.069740 0.104 Uiso 1 1 calc R . . . .
N1 N 0.8176(12) -0.0024(10) 1.0028(7) 0.148(4) 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 0.0033 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'
Br Br -0.2901 2.4595 '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'
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'
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
C5 O1 C4 118.7(4) . .
C18 N5 B1 124.9(4) . .
C21 N5 C18 109.1(4) . .
C21 N5 B1 125.9(4) . .
C12 N4 B1 125.4(4) . .
C15 N4 C12 108.6(4) . .
C15 N4 B1 125.8(4) . .
N5 C18 C11 120.3(4) . .
N5 C18 C19 108.4(4) . .
C11 C18 C19 131.3(5) . .
C18 C11 C9 117.5(4) . .
C12 C11 C18 121.9(4) . .
C12 C11 C9 120.6(5) . .
C12 C13 C17 129.6(5) . .
C14 C13 C12 105.1(4) . .
C14 C13 C17 125.3(5) . .
N4 C12 C13 108.0(4) . .
C11 C12 N4 119.7(5) . .
C11 C12 C13 132.3(5) . .
C10 C9 C11 121.8(4) . .
C8 C9 C11 120.3(4) . .
C8 C9 C10 117.9(4) . .
O1 C5 C6 116.2(4) . .
O1 C5 C7 124.7(5) . .
C7 C5 C6 119.1(5) . .
C13 C14 Br1 126.9(4) . .
C13 C14 C15 110.2(5) . .
C15 C14 Br1 122.8(4) . .
C18 C19 C22 129.7(5) . .
C20 C19 C18 104.7(4) . .
C20 C19 C22 125.5(5) . .
C10 C6 C5 120.4(4) . .
C6 C10 C9 121.0(5) . .
N4 C15 C14 108.1(4) . .
N4 C15 C16 124.1(5) . .
C14 C15 C16 127.8(5) . .
C9 C8 C7 121.8(5) . .
C19 C20 Br2 126.5(4) . .
C19 C20 C21 110.0(5) . .
C21 C20 Br2 123.5(4) . .
N5 C21 C20 107.7(5) . .
N5 C21 C23 124.5(5) . .
C20 C21 C23 127.7(5) . .
C5 C7 C8 119.6(5) . .
C2 C3 C4 114.2(5) . .
O1 C4 C3 107.4(4) . .
N1 N2 N3 173.5(11) . .
F1 B1 N5 110.0(4) . .
F1 B1 N4 110.4(4) . .
F2 B1 F1 109.1(4) . .
F2 B1 N5 109.8(4) . .
F2 B1 N4 110.6(4) . .
N4 B1 N5 107.0(4) . .
C3 C2 C1 112.0(5) . .
N2 N3 C1 113.8(7) . .
N3 C1 C2 112.3(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C14 1.880(5) .
Br2 C20 1.874(5) .
F1 B1 1.379(6) .
F2 B1 1.374(6) .
O1 C5 1.371(5) .
O1 C4 1.435(6) .
N5 C18 1.390(6) .
N5 C21 1.342(6) .
N5 B1 1.549(7) .
N4 C12 1.402(6) .
N4 C15 1.338(6) .
N4 B1 1.542(7) .
C18 C11 1.403(7) .
C18 C19 1.426(7) .
C11 C12 1.386(7) .
C11 C9 1.492(6) .
C13 C12 1.422(7) .
C13 C14 1.371(7) .
C13 C17 1.491(7) .
C9 C10 1.386(6) .
C9 C8 1.365(7) .
C5 C6 1.380(7) .
C5 C7 1.376(7) .
C14 C15 1.395(7) .
C19 C20 1.383(7) .
C19 C22 1.491(7) .
C6 C10 1.368(7) .
C15 C16 1.484(7) .
C8 C7 1.383(7) .
C20 C21 1.402(7) .
C21 C23 1.478(7) .
C3 C4 1.502(7) .
C3 C2 1.479(8) .
N2 N3 1.198(9) .
N2 N1 1.116(10) .
C2 C1 1.516(8) .
N3 C1 1.475(9) .
