#------------------------------------------------------------------------------
#$Date: 2025-09-23 04:19:12 +0300 (Tue, 23 Sep 2025) $
#$Revision: 302220 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/08/7250891.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_7250891
loop_
_publ_author_name
'Schwarze, Thomas'
'Al Akrami, Mazen'
'Heinrich, Julian'
'Hergl, Vinja'
'Sperlich, Eric'
'Kelling, Alexandra'
'Sprenger, Tobias'
'Jahn, Nicolas'
'Klamroth, Tillmann'
'Kulak, Nora'
_publ_section_title
;
 A sodium ion-selective photosensitizer: Dibrominated F-BODIPY as a
 fluorescence imaging and therapeutic agent
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D5CP03172A
_journal_year                    2025
_chemical_formula_moiety         'C27 H31 B Br2 Cl F2 N2 Na O9'
_chemical_formula_sum            'C27 H31 B Br2 Cl F2 N2 Na O9'
_chemical_formula_weight         794.61
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-07-30 deposited with the CCDC.	2025-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                106.347(4)
_cell_angle_beta                 96.538(4)
_cell_angle_gamma                98.274(4)
_cell_formula_units_Z            2
_cell_length_a                   8.3777(4)
_cell_length_b                   10.8636(5)
_cell_length_c                   18.1118(8)
_cell_measurement_reflns_used    23148
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      31.22
_cell_measurement_theta_min      2.89
_cell_volume                     1544.47(13)
_computing_cell_refinement
;
X-Area Recipe 1.37.0.0 (STOE, 2021)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.186.0 (STOE, 2022)
;
_computing_data_reduction
;
X-Area Integrate 2.5.3.0 (STOE, 2021)
X-Area LANA 2.7.5.0 (STOE, 2022)
;
_computing_molecular_graphics    'Diamond (Blankenburg, 2022)'
_computing_publication_material
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 2.1, Darmstadt 2022
;
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2022)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      210
_diffrn_detector                 'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      ' 2985 frames, detector distance = 60 mm'
_diffrn_measurement_device       '4-circle goniometer'
_diffrn_measurement_device_type  'STOE StadiVari'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.3 mm diameter'
_diffrn_radiation_monochromator  'graded multilayer mirror'
_diffrn_radiation_source         'Genix Microfocus'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25754
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.490
_diffrn_source_current           1.000
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.795
_exptl_absorpt_correction_T_max  0.6207
_exptl_absorpt_correction_T_min  0.4648
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.025
_exptl_crystal_size_rad          0.058
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         5404
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0583
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0579P)²+3.1249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1429
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3255
_reflns_number_total             5404
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cp03172a2.cif
_cod_data_source_block           15erBr2_NaClO4_w3
_cod_database_code               7250891
_shelx_shelxl_version_number     2019/3
_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.
;
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 0.01236(9) -0.30676(7) 0.22923(4) 0.0611(3) Uani 1 1 d . . . . .
Br2 Br -0.40282(10) 0.27737(7) -0.09064(4) 0.0655(3) Uani 1 1 d . . . . .
Cl1 Cl 0.5759(2) 0.69568(16) 0.58627(10) 0.0541(4) Uani 1 1 d . . . . .
Na1 Na 0.3374(3) 0.6333(2) 0.40943(12) 0.0444(6) Uani 1 1 d . . . . .
F1 F -0.0903(4) -0.1420(3) -0.04886(18) 0.0485(9) Uani 1 1 d . . . . .
F2 F -0.3486(4) -0.2346(3) -0.04725(18) 0.0493(9) Uani 1 1 d . . . . .
O1 O 0.0453(4) 0.5395(4) 0.3960(2) 0.0382(9) Uani 1 1 d . . . . .
O2 O 0.1227(5) 0.7963(4) 0.4406(2) 0.0546(12) Uani 1 1 d . . . . .
O3 O 0.4260(5) 0.8578(4) 0.4023(2) 0.0481(11) Uani 1 1 d . . . . .
O5 O 0.2166(4) 0.4787(3) 0.28498(19) 0.0354(9) Uani 1 1 d . . . . .
O9 O 0.5997(7) 0.7882(5) 0.6622(3) 0.0850(16) Uani 1 1 d . . . . .
N1 N -0.1677(5) -0.1359(4) 0.0755(2) 0.0356(11) Uani 1 1 d . . . . .
N2 N -0.2733(5) 0.0008(4) -0.0009(2) 0.0339(11) Uani 1 1 d . . . . .
C1 C -0.0643(7) 0.6112(6) 0.4381(3) 0.0394(14) Uani 1 1 d . . . . .
H1A H -0.115458 0.562931 0.470233 0.047 Uiso 1 1 calc R U . . .
H1B H -0.150514 0.625760 0.401899 0.047 Uiso 1 1 calc R U . . .
C2 C 0.0369(8) 0.7391(6) 0.4887(3) 0.0455(16) Uani 1 1 d . . . . .
H2A H -0.033707 0.796620 0.514190 0.055 Uiso 1 1 calc R U . . .
H2B H 0.113822 0.724813 0.529086 0.055 Uiso 1 1 calc R U . . .
C3 C 0.2264(8) 0.9181(6) 0.4796(4) 0.0525(17) Uani 1 1 d . . . . .
H3A H 0.297315 0.911743 0.524800 0.063 Uiso 1 1 calc R U . . .
H3B H 0.161123 0.985211 0.497921 0.063 Uiso 1 1 calc R U . . .
C4 C 0.3252(8) 0.9521(6) 0.4238(4) 0.0581(18) Uani 1 1 d . . . . .
H4A H 0.253638 0.953645 0.377477 0.070 Uiso 1 1 calc R U . . .
H4B H 0.393069 1.038969 0.447593 0.070 Uiso 1 1 calc R U . . .
C5 C 0.4980(9) 0.8642(7) 0.3349(4) 0.061(2) Uani 1 1 d . . . . .
H5A H 0.561036 0.951640 0.343155 0.073 Uiso 1 1 calc R U . A 3
H5B H 0.413575 0.842791 0.288763 0.073 Uiso 1 1 calc R U . A 3
C8 C 0.3273(7) 0.4446(5) 0.2313(3) 0.0403(15) Uani 1 1 d . . . . .
H8A H 0.267087 0.404320 0.178230 0.048 Uiso 1 1 calc R U . B 3
H8B H 0.390069 0.382527 0.245108 0.048 Uiso 1 1 calc R U . B 3
C9 C 0.0737(6) 0.3929(5) 0.2769(3) 0.0276(12) Uani 1 1 d . . . . .
C10 C 0.0186(7) 0.2818(5) 0.2164(3) 0.0311(13) Uani 1 1 d . . . . .
H10 H 0.085100 0.255171 0.178591 0.037 Uiso 1 1 calc R U . . .
C11 C -0.1357(7) 0.2066(5) 0.2096(3) 0.0331(13) Uani 1 1 d . . . . .
C12 C -0.2335(7) 0.2457(5) 0.2648(3) 0.0360(14) Uani 1 1 d . . . . .
H12 H -0.338492 0.197129 0.260064 0.043 Uiso 1 1 calc R U . . .
C13 C -0.1757(7) 0.3574(6) 0.3275(3) 0.0387(14) Uani 1 1 d . . . . .
H13 H -0.241971 0.383585 0.365461 0.046 Uiso 1 1 calc R U . . .
C14 C -0.0236(7) 0.4302(5) 0.3349(3) 0.0313(13) Uani 1 1 d . . . . .
C15 C -0.1859(6) 0.0889(5) 0.1397(3) 0.0315(13) Uani 1 1 d . . . . .
C16 C -0.1500(7) -0.0322(5) 0.1436(3) 0.0342(13) Uani 1 1 d . . . . .
C17 C -0.0849(7) -0.0712(6) 0.2077(3) 0.0380(14) Uani 1 1 d . . . . .
C18 C -0.0680(7) -0.1991(6) 0.1749(3) 0.0418(15) Uani 1 1 d . . . . .
C19 C -0.1153(7) -0.2368(6) 0.0949(3) 0.0431(15) Uani 1 1 d . . . . .
C20 C -0.3214(7) 0.0443(6) -0.0605(3) 0.0393(15) Uani 1 1 d . . . . .
C21 C -0.3335(7) 0.1738(6) -0.0299(3) 0.0395(14) Uani 1 1 d . . . . .
C22 C -0.2924(6) 0.2156(5) 0.0504(3) 0.0339(13) Uani 1 1 d . . . . .
C23 C -0.2511(6) 0.1041(5) 0.0692(3) 0.0307(13) Uani 1 1 d . . . . .
C24 C -0.0449(8) 0.0058(6) 0.2931(3) 0.0457(16) Uani 1 1 d . . . . .
H24A H -0.024208 -0.052240 0.323652 0.069 Uiso 1 1 calc R U . . .
H24B H -0.136304 0.046786 0.308720 0.069 Uiso 1 1 calc R U . . .
H24C H 0.051554 0.072537 0.301783 0.069 Uiso 1 1 calc R U . . .
C25 C -0.1096(9) -0.3610(6) 0.0350(4) 0.0573(18) Uani 1 1 d . . . . .
H25A H -0.045962 -0.412326 0.058427 0.086 Uiso 1 1 calc R U . . .
H25B H -0.059254 -0.342147 -0.007164 0.086 Uiso 1 1 calc R U . . .
H25C H -0.219825 -0.409817 0.014761 0.086 Uiso 1 1 calc R U . . .
C26 C -0.3483(8) -0.0346(6) -0.1445(3) 0.0528(17) Uani 1 1 d . . . . .
H26A H -0.429188 -0.003427 -0.173785 0.079 Uiso 1 1 calc R U . . .
H26B H -0.387008 -0.125634 -0.149505 0.079 Uiso 1 1 calc R U . . .
H26C H -0.246305 -0.026086 -0.164692 0.079 Uiso 1 1 calc R U . . .
C27 C -0.2930(8) 0.3488(6) 0.1039(3) 0.0467(16) Uani 1 1 d . . . . .
H27A H -0.349515 0.340668 0.146629 0.070 Uiso 1 1 calc R U . . .
H27B H -0.348427 0.397831 0.075268 0.070 Uiso 1 1 calc R U . . .
H27C H -0.181279 0.394044 0.124445 0.070 Uiso 1 1 calc R U . . .
B1 B -0.2209(8) -0.1323(7) -0.0084(4) 0.0376(16) Uani 1 1 d . . . . .
O6A O 0.7153(17) 0.7194(12) 0.5557(10) 0.098(5) Uani 0.68(3) 1 d . U P C 1
O7A O 0.535(2) 0.5674(11) 0.5957(6) 0.068(4) Uani 0.68(3) 1 d . U P C 1
O8A O 0.440(2) 0.7183(15) 0.5459(8) 0.062(4) Uani 0.68(3) 1 d . U P C 1
O6B O 0.642(5) 0.722(3) 0.516(2) 0.109(10) Uani 0.32(3) 1 d . U P C 2
O7B O 0.625(5) 0.575(2) 0.5817(17) 0.082(10) Uani 0.32(3) 1 d . U P C 2
O8B O 0.397(4) 0.671(4) 0.5392(18) 0.074(9) Uani 0.32(3) 1 d . U P C 2
O4A O 0.5234(7) 0.6321(5) 0.3140(3) 0.045(2) Uani 0.820(16) 1 d . U P C 3
C6A C 0.6121(16) 0.7608(12) 0.3247(8) 0.053(3) Uani 0.820(16) 1 d . U P C 3
H6A H 0.666404 0.760400 0.279497 0.063 Uiso 0.820(16) 1 calc R U P C 3
H6B H 0.696894 0.785494 0.370930 0.063 Uiso 0.820(16) 1 calc R U P C 3
C7A C 0.4397(15) 0.5687(10) 0.2364(7) 0.047(3) Uani 0.820(16) 1 d . U P C 3
H7A H 0.519733 0.548776 0.201360 0.056 Uiso 0.820(16) 1 calc R U P C 3
H7B H 0.376106 0.627534 0.219286 0.056 Uiso 0.820(16) 1 calc R U P C 3
O4B O 0.431(3) 0.670(2) 0.2838(13) 0.036(10) Uani 0.180(16) 1 d . U P C 4
C6B C 0.566(5) 0.774(4) 0.308(2) 0.017(10) Uani 0.180(16) 1 d . U P C 4
H6C H 0.647497 0.762039 0.347082 0.021 Uiso 0.180(16) 1 calc R U P C 4
H6D H 0.617238 0.784934 0.263500 0.021 Uiso 0.180(16) 1 calc R U P C 4
C7B C 0.468(5) 0.539(4) 0.252(2) 0.019(11) Uani 0.180(16) 1 d . U P C 4
H7C H 0.520967 0.535617 0.206522 0.023 Uiso 0.180(16) 1 calc R U P C 4
H7D H 0.543531 0.520896 0.291539 0.023 Uiso 0.180(16) 1 calc R U P C 4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0014 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2713 2.4705 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1507 0.1611 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0180 0.0106 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0371 0.0257 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 '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
_geom_angle_publ_flag
O6A Cl1 O8A 113.4(9) . . ?
O6A Cl1 O9 106.6(6) . . ?
O8A Cl1 O9 105.4(7) . . ?
O7B Cl1 O9 116.6(11) . . ?
O6A Cl1 O7A 116.3(7) . . ?
O8A Cl1 O7A 107.6(7) . . ?
O9 Cl1 O7A 107.0(5) . . ?
O7B Cl1 O6B 99.3(18) . . ?
O9 Cl1 O6B 125.0(15) . . ?
O7B Cl1 O8B 109.9(15) . . ?
O9 Cl1 O8B 113.8(12) . . ?
O6B Cl1 O8B 88.4(19) . . ?
O8B Na1 O7B 77.8(14) . 2_666 ?
O8B Na1 O5 147.1(10) . . ?
O7B Na1 O5 73.7(6) 2_666 . ?
O8A Na1 O5 159.8(4) . . ?
O5 Na1 O4A 69.24(16) . . ?
O8B Na1 O1 96.5(8) . . ?
O7B Na1 O1 83.2(11) 2_666 . ?
O8A Na1 O1 106.8(4) . . ?
O5 Na1 O1 64.25(13) . . ?
O4A Na1 O1 132.45(18) . . ?
O8B Na1 O3 99.5(10) . . ?
O7B Na1 O3 155.4(11) 2_666 . ?
O8A Na1 O3 87.0(4) . . ?
O5 Na1 O3 113.23(15) . . ?
O4A Na1 O3 69.33(16) . . ?
O1 Na1 O3 121.24(16) . . ?
O8A Na1 O7A 89.5(4) . 2_666 ?
O5 Na1 O7A 75.2(3) . 2_666 ?
O1 Na1 O7A 100.6(4) . 2_666 ?
O3 Na1 O7A 137.2(4) . 2_666 ?
O5 Na1 O4B 61.1(5) . . ?
O1 Na1 O4B 115.4(6) . . ?
O3 Na1 O4B 59.4(5) . . ?
O8B Na1 O2 86.7(9) . . ?
O7B Na1 O2 139.3(12) 2_666 . ?
O8A Na1 O2 84.8(3) . . ?
O5 Na1 O2 104.36(14) . . ?
O4A Na1 O2 124.94(19) . . ?
O1 Na1 O2 61.16(13) . . ?
O3 Na1 O2 63.86(14) . . ?
O7A Na1 O2 158.0(4) 2_666 . ?
O4B Na1 O2 102.7(6) . . ?
O8B Na1 O6B 47.9(10) . . ?
O7B Na1 O6B 83.3(9) 2_666 . ?
O5 Na1 O6B 141.2(5) . . ?
O1 Na1 O6B 143.9(5) . . ?
O3 Na1 O6B 77.4(5) . . ?
O2 Na1 O6B 113.4(5) . . ?
O5 Na1 C7B 47.1(8) . . ?
O1 Na1 C7B 111.2(8) . . ?
O3 Na1 C7B 85.7(8) . . ?
O4B Na1 C7B 27.8(10) . . ?
O2 Na1 C7B 126.4(7) . . ?
C14 O1 C1 117.1(4) . . ?
C14 O1 Na1 119.5(3) . . ?
C1 O1 Na1 121.8(3) . . ?
C2 O2 C3 115.1(5) . . ?
C2 O2 Na1 99.0(3) . . ?
C3 O2 Na1 102.5(3) . . ?
C4 O3 C5 112.9(5) . . ?
C4 O3 Na1 119.4(4) . . ?
C5 O3 Na1 114.9(4) . . ?
C9 O5 C8 118.9(4) . . ?
C9 O5 Na1 120.9(3) . . ?
C8 O5 Na1 115.4(3) . . ?
C19 N1 C16 108.0(5) . . ?
C19 N1 B1 125.7(5) . . ?
C16 N1 B1 126.0(5) . . ?
C20 N2 C23 108.8(4) . . ?
C20 N2 B1 125.5(4) . . ?
C23 N2 B1 124.9(4) . . ?
O1 C1 C2 106.5(4) . . ?
O1 C1 H1A 110.4 . . ?
C2 C1 H1A 110.4 . . ?
O1 C1 H1B 110.4 . . ?
C2 C1 H1B 110.4 . . ?
H1A C1 H1B 108.6 . . ?
O2 C2 C1 107.8(4) . . ?
O2 C2 H2A 110.1 . . ?
C1 C2 H2A 110.1 . . ?
O2 C2 H2B 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.5 . . ?
O2 C3 C4 107.5(5) . . ?
O2 C3 H3A 110.2 . . ?
C4 C3 H3A 110.2 . . ?
O2 C3 H3B 110.2 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
O3 C4 C3 108.9(5) . . ?
O3 C4 H4A 109.9 . . ?
C3 C4 H4A 109.9 . . ?
O3 C4 H4B 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C6B C5 O3 115(2) . . ?
O3 C5 C6A 104.8(7) . . ?
O3 C5 H5A 110.8 . . ?
C6A C5 H5A 110.8 . . ?
O3 C5 H5B 110.8 . . ?
C6A C5 H5B 110.8 . . ?
H5A C5 H5B 108.9 . . ?
C7B C8 O5 110.1(18) . . ?
O5 C8 C7A 107.0(6) . . ?
O5 C8 H8A 110.3 . . ?
C7A C8 H8A 110.3 . . ?
O5 C8 H8B 110.3 . . ?
C7A C8 H8B 110.3 . . ?
H8A C8 H8B 108.6 . . ?
C10 C9 O5 125.1(5) . . ?
C10 C9 C14 119.5(5) . . ?
O5 C9 C14 115.3(4) . . ?
C9 C10 C11 120.9(5) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 119.6(5) . . ?
C12 C11 C15 124.0(5) . . ?
C10 C11 C15 116.4(5) . . ?
C11 C12 C13 119.5(5) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 121.0(5) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 O1 125.0(5) . . ?
C13 C14 C9 119.4(5) . . ?
O1 C14 C9 115.6(5) . . ?
C23 C15 C16 121.0(5) . . ?
C23 C15 C11 118.9(5) . . ?
C16 C15 C11 119.7(5) . . ?
N1 C16 C15 119.9(5) . . ?
N1 C16 C17 108.8(5) . . ?
C15 C16 C17 131.1(5) . . ?
C18 C17 C16 104.5(5) . . ?
C18 C17 C24 126.5(5) . . ?
C16 C17 C24 128.9(5) . . ?
C19 C18 C17 110.4(5) . . ?
C19 C18 Br1 124.0(4) . . ?
C17 C18 Br1 125.6(4) . . ?
N1 C19 C18 108.3(5) . . ?
N1 C19 C25 122.0(5) . . ?
C18 C19 C25 129.8(6) . . ?
N2 C20 C21 107.7(5) . . ?
N2 C20 C26 124.7(5) . . ?
C21 C20 C26 127.6(5) . . ?
C22 C21 C20 111.3(5) . . ?
C22 C21 Br2 124.9(5) . . ?
C20 C21 Br2 123.8(4) . . ?
C21 C22 C23 104.3(5) . . ?
C21 C22 C27 126.7(5) . . ?
C23 C22 C27 129.0(5) . . ?
C15 C23 N2 120.7(5) . . ?
C15 C23 C22 131.2(5) . . ?
N2 C23 C22 107.9(4) . . ?
C17 C24 H24A 109.5 . . ?
C17 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C17 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C19 C25 H25A 109.5 . . ?
C19 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C19 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C20 C26 H26A 109.5 . . ?
C20 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C20 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
F1 B1 F2 109.1(5) . . ?
F1 B1 N2 109.6(5) . . ?
F2 B1 N2 111.1(5) . . ?
F1 B1 N1 109.7(5) . . ?
F2 B1 N1 110.4(5) . . ?
N2 B1 N1 106.7(4) . . ?
Cl1 O7A Na1 139.7(11) . 2_666 ?
Cl1 O8A Na1 128.2(9) . . ?
Cl1 O6B Na1 96.7(19) . . ?
Cl1 O7B Na1 168(3) . 2_666 ?
Cl1 O8B Na1 124.7(16) . . ?
C7A O4A C6A 113.5(7) . . ?
C7A O4A Na1 111.3(5) . . ?
C6A O4A Na1 111.4(6) . . ?
O4A C6A C5 112.0(9) . . ?
O4A C6A H6A 109.2 . . ?
C5 C6A H6A 109.2 . . ?
O4A C6A H6B 109.2 . . ?
C5 C6A H6B 109.2 . . ?
H6A C6A H6B 107.9 . . ?
O4A C7A C8 111.3(8) . . ?
O4A C7A H7A 109.4 . . ?
C8 C7A H7A 109.4 . . ?
O4A C7A H7B 109.4 . . ?
C8 C7A H7B 109.4 . . ?
H7A C7A H7B 108.0 . . ?
C6B O4B C7B 117(3) . . ?
C6B O4B Na1 107(2) . . ?
C7B O4B Na1 96(2) . . ?
C5 C6B O4B 100(3) . . ?
C5 C6B H6C 111.7 . . ?
O4B C6B H6C 111.7 . . ?
C5 C6B H6D 111.7 . . ?
O4B C6B H6D 111.7 . . ?
H6C C6B H6D 109.5 . . ?
C8 C7B O4B 112(3) . . ?
C8 C7B Na1 84.3(19) . . ?
O4B C7B Na1 56.1(16) . . ?
C8 C7B H7C 109.3 . . ?
O4B C7B H7C 109.3 . . ?
Na1 C7B H7C 163.9 . . ?
C8 C7B H7D 109.3 . . ?
O4B C7B H7D 109.3 . . ?
Na1 C7B H7D 74.1 . . ?
H7C C7B H7D 108.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C18 1.875(6) . ?
Br2 C21 1.885(6) . ?
Cl1 O6A 1.370(9) . ?
Cl1 O8A 1.374(12) . ?
Cl1 O7B 1.42(2) . ?
Cl1 O9 1.429(5) . ?
Cl1 O7A 1.448(12) . ?
Cl1 O6B 1.52(3) . ?
Cl1 O8B 1.58(3) . ?
Na1 O8B 2.25(3) . ?
Na1 O7B 2.37(2) 2_666 ?
Na1 O8A 2.388(14) . ?
Na1 O5 2.405(4) . ?
Na1 O4A 2.454(5) . ?
Na1 O1 2.468(4) . ?
Na1 O3 2.489(5) . ?
Na1 O7A 2.545(14) 2_666 ?
Na1 O4B 2.60(2) . ?
Na1 O2 2.698(5) . ?
Na1 O6B 2.88(5) . ?
Na1 C7B 3.12(4) . ?
F1 B1 1.385(7) . ?
F2 B1 1.386(7) . ?
O1 C14 1.373(6) . ?
O1 C1 1.437(6) . ?
O2 C2 1.407(7) . ?
O2 C3 1.417(7) . ?
O3 C4 1.419(7) . ?
O3 C5 1.437(7) . ?
O5 C9 1.373(6) . ?
O5 C8 1.429(6) . ?
N1 C19 1.356(7) . ?
N1 C16 1.392(6) . ?
N1 B1 1.548(8) . ?
N2 C20 1.339(7) . ?
N2 C23 1.411(6) . ?
N2 B1 1.545(8) . ?
C1 C2 1.502(8) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 C4 1.469(9) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 C6B 1.22(4) . ?
C5 C6A 1.563(14) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C8 C7B 1.38(4) . ?
C8 C7A 1.503(12) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C10 1.360(7) . ?
C9 C14 1.409(7) . ?
C10 C11 1.399(7) . ?
C10 H10 0.9400 . ?
C11 C12 1.378(7) . ?
C11 C15 1.493(7) . ?
C12 C13 1.388(7) . ?
C12 H12 0.9400 . ?
C13 C14 1.371(8) . ?
C13 H13 0.9400 . ?
C15 C23 1.392(7) . ?
C15 C16 1.410(7) . ?
C16 C17 1.423(7) . ?
C17 C18 1.384(8) . ?
C17 C24 1.509(8) . ?
C18 C19 1.383(8) . ?
C19 C25 1.485(8) . ?
C20 C21 1.383(8) . ?
C20 C26 1.494(7) . ?
C21 C22 1.382(7) . ?
C22 C23 1.424(7) . ?
C22 C27 1.499(8) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 H26C 0.9700 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 H27C 0.9700 . ?
O4A C7A 1.425(13) . ?
O4A C6A 1.436(12) . ?
C6A H6A 0.9800 . ?
C6A H6B 0.9800 . ?
C7A H7A 0.9800 . ?
C7A H7B 0.9800 . ?
O4B C6B 1.41(5) . ?
O4B C7B 1.46(5) . ?
C6B H6C 0.9800 . ?
C6B H6D 0.9800 . ?
C7B H7C 0.9800 . ?
C7B H7D 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2A O6A^a 0.98 2.43 3.083(11) 123.8 1_455 yes
C2 H2B O8B^b 0.98 2.52 3.30(3) 136.0 . yes
C3 H3A O8A^a 0.98 2.66 3.383(13) 131.1 . yes
C4 H4B O6B^b 0.98 2.57 3.36(3) 138.3 2_676 yes
C10 H10 F1 0.94 2.33 3.155(6) 145.7 2 yes
C13 H13 O8B^b 0.94 2.43 3.26(3) 147.9 2_566 yes
C25 H25A Br1 0.97 2.94 3.406(7) 111.0 . yes
C25 H25B F1 0.97 2.53 3.158(7) 122.4 . yes
C26 H26B F2 0.97 2.48 3.159(8) 126.9 . yes
C7A^c H7B^c Br2 0.98 2.82 3.508(12) 127.9 2_565 yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 O1 C1 C2 -167.7(4) . . . . ?
Na1 O1 C1 C2 -2.4(6) . . . . ?
C3 O2 C2 C1 -179.3(5) . . . . ?
Na1 O2 C2 C1 -70.9(5) . . . . ?
O1 C1 C2 O2 53.0(6) . . . . ?
C2 O2 C3 C4 170.7(5) . . . . ?
Na1 O2 C3 C4 64.4(5) . . . . ?
C5 O3 C4 C3 166.1(5) . . . . ?
Na1 O3 C4 C3 26.3(6) . . . . ?
O2 C3 C4 O3 -63.7(7) . . . . ?
C4 O3 C5 C6B -170(2) . . . . ?
Na1 O3 C5 C6B -28(2) . . . . ?
C4 O3 C5 C6A 176.2(6) . . . . ?
Na1 O3 C5 C6A -42.2(7) . . . . ?
C9 O5 C8 C7B -176.1(18) . . . . ?
Na1 O5 C8 C7B -20.1(18) . . . . ?
C9 O5 C8 C7A 161.6(6) . . . . ?
Na1 O5 C8 C7A -42.5(7) . . . . ?
C8 O5 C9 C10 -7.2(7) . . . . ?
Na1 O5 C9 C10 -161.8(4) . . . . ?
C8 O5 C9 C14 176.3(5) . . . . ?
Na1 O5 C9 C14 21.7(6) . . . . ?
O5 C9 C10 C11 -174.2(5) . . . . ?
C14 C9 C10 C11 2.2(8) . . . . ?
C9 C10 C11 C12 0.2(8) . . . . ?
C9 C10 C11 C15 178.2(5) . . . . ?
C10 C11 C12 C13 -1.7(8) . . . . ?
C15 C11 C12 C13 -179.5(5) . . . . ?
C11 C12 C13 C14 0.7(8) . . . . ?
C12 C13 C14 O1 -177.9(5) . . . . ?
C12 C13 C14 C9 1.7(8) . . . . ?
C1 O1 C14 C13 -25.0(7) . . . . ?
Na1 O1 C14 C13 169.4(4) . . . . ?
C1 O1 C14 C9 155.4(5) . . . . ?
Na1 O1 C14 C9 -10.2(6) . . . . ?
C10 C9 C14 C13 -3.1(8) . . . . ?
O5 C9 C14 C13 173.6(5) . . . . ?
C10 C9 C14 O1 176.5(4) . . . . ?
O5 C9 C14 O1 -6.8(7) . . . . ?
C12 C11 C15 C23 95.7(7) . . . . ?
C10 C11 C15 C23 -82.2(6) . . . . ?
C12 C11 C15 C16 -91.4(7) . . . . ?
C10 C11 C15 C16 90.7(6) . . . . ?
C19 N1 C16 C15 175.9(5) . . . . ?
B1 N1 C16 C15 1.7(8) . . . . ?
C19 N1 C16 C17 -0.4(6) . . . . ?
B1 N1 C16 C17 -174.7(5) . . . . ?
C23 C15 C16 N1 5.0(8) . . . . ?
C11 C15 C16 N1 -167.7(5) . . . . ?
C23 C15 C16 C17 -179.6(5) . . . . ?
C11 C15 C16 C17 7.7(9) . . . . ?
N1 C16 C17 C18 -0.7(6) . . . . ?
C15 C16 C17 C18 -176.5(6) . . . . ?
N1 C16 C17 C24 -179.6(5) . . . . ?
C15 C16 C17 C24 4.6(10) . . . . ?
C16 C17 C18 C19 1.6(7) . . . . ?
C24 C17 C18 C19 -179.5(5) . . . . ?
C16 C17 C18 Br1 -180.0(4) . . . . ?
C24 C17 C18 Br1 -1.0(9) . . . . ?
C16 N1 C19 C18 1.4(6) . . . . ?
B1 N1 C19 C18 175.7(5) . . . . ?
C16 N1 C19 C25 -176.8(5) . . . . ?
B1 N1 C19 C25 -2.5(9) . . . . ?
C17 C18 C19 N1 -1.9(7) . . . . ?
Br1 C18 C19 N1 179.6(4) . . . . ?
C17 C18 C19 C25 176.1(6) . . . . ?
Br1 C18 C19 C25 -2.4(10) . . . . ?
C23 N2 C20 C21 -1.0(6) . . . . ?
B1 N2 C20 C21 -171.0(5) . . . . ?
C23 N2 C20 C26 176.4(5) . . . . ?
B1 N2 C20 C26 6.5(9) . . . . ?
N2 C20 C21 C22 0.2(7) . . . . ?
C26 C20 C21 C22 -177.1(5) . . . . ?
N2 C20 C21 Br2 -178.3(4) . . . . ?
C26 C20 C21 Br2 4.4(9) . . . . ?
C20 C21 C22 C23 0.7(6) . . . . ?
Br2 C21 C22 C23 179.1(4) . . . . ?
C20 C21 C22 C27 -179.2(5) . . . . ?
Br2 C21 C22 C27 -0.7(8) . . . . ?
C16 C15 C23 N2 -4.0(8) . . . . ?
C11 C15 C23 N2 168.8(5) . . . . ?
C16 C15 C23 C22 -178.0(5) . . . . ?
C11 C15 C23 C22 -5.2(9) . . . . ?
C20 N2 C23 C15 -173.8(5) . . . . ?
B1 N2 C23 C15 -3.8(8) . . . . ?
C20 N2 C23 C22 1.5(6) . . . . ?
B1 N2 C23 C22 171.5(5) . . . . ?
C21 C22 C23 C15 173.3(5) . . . . ?
C27 C22 C23 C15 -6.9(10) . . . . ?
C21 C22 C23 N2 -1.3(6) . . . . ?
C27 C22 C23 N2 178.6(5) . . . . ?
C20 N2 B1 F1 58.3(7) . . . . ?
C23 N2 B1 F1 -110.0(5) . . . . ?
C20 N2 B1 F2 -62.4(7) . . . . ?
C23 N2 B1 F2 129.2(5) . . . . ?
C20 N2 B1 N1 177.1(5) . . . . ?
C23 N2 B1 N1 8.8(7) . . . . ?
C19 N1 B1 F1 -62.3(7) . . . . ?
C16 N1 B1 F1 111.0(6) . . . . ?
C19 N1 B1 F2 58.0(7) . . . . ?
C16 N1 B1 F2 -128.7(5) . . . . ?
C19 N1 B1 N2 178.9(5) . . . . ?
C16 N1 B1 N2 -7.8(7) . . . . ?
O6A Cl1 O7A Na1 11.2(13) . . . 2_666 ?
O8A Cl1 O7A Na1 139.5(10) . . . 2_666 ?
O9 Cl1 O7A Na1 -107.7(9) . . . 2_666 ?
O6A Cl1 O8A Na1 52.9(14) . . . . ?
O9 Cl1 O8A Na1 169.0(9) . . . . ?
O7A Cl1 O8A Na1 -77.1(11) . . . . ?
O7B Cl1 O6B Na1 99.4(13) . . . . ?
O9 Cl1 O6B Na1 -128.8(11) . . . . ?
O8B Cl1 O6B Na1 -10.6(15) . . . . ?
O9 Cl1 O7B Na1 64(8) . . . 2_666 ?
O6B Cl1 O7B Na1 -159(8) . . . 2_666 ?
O8B Cl1 O7B Na1 -67(7) . . . 2_666 ?
O7B Cl1 O8B Na1 -83(2) . . . . ?
O9 Cl1 O8B Na1 144.3(18) . . . . ?
O6B Cl1 O8B Na1 16(3) . . . . ?
C7A O4A C6A C5 79.9(11) . . . . ?
Na1 O4A C6A C5 -46.7(10) . . . . ?
O3 C5 C6A O4A 59.3(10) . . . . ?
C6A O4A C7A C8 -170.6(8) . . . . ?
Na1 O4A C7A C8 -44.0(10) . . . . ?
O5 C8 C7A O4A 57.4(10) . . . . ?
O3 C5 C6B O4B 64(3) . . . . ?
C7B O4B C6B C5 -176(3) . . . . ?
Na1 O4B C6B C5 -69(3) . . . . ?
O5 C8 C7B O4B -36(3) . . . . ?
O5 C8 C7B Na1 13.9(12) . . . . ?
C6B O4B C7B C8 180(3) . . . . ?
Na1 O4B C7B C8 67(3) . . . . ?
C6B O4B C7B Na1 113(3) . . . . ?
