#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:31:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180303 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/17/7151768.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_7151768
loop_
_publ_author_name
'Guo, Huimin'
'Jing, Yingying'
'Yuan, Xiaolin'
'Ji, Shaomin'
'Zhao, Jianzhang'
'Li, Xiaohuan'
'Kan, Yanyan'
_publ_section_title
;
 Highly selective fluorescent OFF-ON thiol probes based on dyads of
 BODIPY and potent intramolecular electron sink
 2,4-dinitrobenzenesulfonyl subunits.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3844
_journal_page_last               3853
_journal_paper_doi               10.1039/c0ob00910e
_journal_volume                  9
_journal_year                    2011
_chemical_formula_sum            'C25 H21 B F2 N4 O7 S'
_chemical_formula_weight         570.33
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.666(4)
_cell_angle_beta                 95.646(4)
_cell_angle_gamma                94.209(4)
_cell_formula_units_Z            4
_cell_length_a                   8.9837(5)
_cell_length_b                   16.6227(10)
_cell_length_c                   17.0722(9)
_cell_measurement_temperature    273(2)
_cell_volume                     2515.8(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0643
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19436
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.21
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    'riding mode'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     721
_refine_ls_number_reflns         8744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0613
_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)+(0.1060P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1637
_refine_ls_wR_factor_ref         0.1913
_reflns_number_gt                5138
_reflns_number_total             8744
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00910e.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      'P-1 '
_cod_database_code               7151768
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.92826(11) 0.16536(6) 0.30780(5) 0.0550(3) Uani 1 1 d . . .
S2 S 0.92069(13) 0.39193(6) -0.18994(6) 0.0628(3) Uani 1 1 d . . .
O1 O 0.9162(3) 0.17137(14) 0.21634(13) 0.0526(6) Uani 1 1 d . . .
O2 O 1.0363(3) 0.22899(19) 0.34109(15) 0.0755(9) Uani 1 1 d . . .
O3 O 0.9468(3) 0.08385(17) 0.32193(15) 0.0720(8) Uani 1 1 d . . .
O4 O 0.7640(4) 0.40167(17) 0.35627(18) 0.0876(10) Uani 1 1 d . . .
O5 O 0.8428(4) 0.32812(17) 0.26139(16) 0.0744(8) Uani 1 1 d . . .
O6 O 0.2805(3) 0.17060(19) 0.46460(19) 0.0826(9) Uani 1 1 d . . .
O7 O 0.3283(3) 0.29888(19) 0.46155(18) 0.0774(9) Uani 1 1 d . . .
O8 O 0.9156(3) 0.37512(14) -0.28273(13) 0.0523(6) Uani 1 1 d . . .
O9 O 0.9032(4) 0.47464(17) -0.16809(16) 0.0835(9) Uani 1 1 d . . .
O10 O 1.0497(3) 0.35576(19) -0.15952(16) 0.0826(9) Uani 1 1 d . . .
O11 O 0.8732(4) 0.1378(2) -0.1568(2) 0.1010(12) Uani 1 1 d . . .
O12 O 0.9212(4) 0.21358(18) -0.24876(17) 0.0749(8) Uani 1 1 d . . .
O13 O 0.2679(6) 0.2514(4) -0.0884(3) 0.187(3) Uani 1 1 d . . .
O14 O 0.3917(7) 0.1550(5) -0.0647(5) 0.234(4) Uani 1 1 d . . .
N1 N 0.4701(3) 0.27930(18) 0.15246(16) 0.0504(8) Uani 1 1 d . . .
N2 N 0.6770(3) 0.34488(17) 0.08932(16) 0.0496(8) Uani 1 1 d . . .
N3 N 0.7733(4) 0.33673(19) 0.31855(18) 0.0535(8) Uani 1 1 d . . .
N4 N 0.3555(4) 0.2281(2) 0.44725(18) 0.0551(8) Uani 1 1 d . . .
N5 N 0.4770(3) 0.19760(16) -0.35061(15) 0.0431(7) Uani 1 1 d . . .
N6 N 0.7090(3) 0.15699(16) -0.40446(15) 0.0412(7) Uani 1 1 d . . .
N7 N 0.8574(4) 0.1978(2) -0.1926(2) 0.0643(9) Uani 1 1 d . . .
N8 N 0.3787(6) 0.2178(4) -0.0872(3) 0.1181(18) Uani 1 1 d . . .
F1 F 0.5509(4) 0.41967(16) 0.18558(19) 0.1143(11) Uani 1 1 d . . .
F2 F 0.4246(3) 0.38171(19) 0.06563(19) 0.1117(11) Uani 1 1 d . . .
F3 F 0.4865(2) 0.06487(12) -0.42004(13) 0.0647(6) Uani 1 1 d . . .
F4 F 0.6117(3) 0.09204(13) -0.29793(12) 0.0662(6) Uani 1 1 d . . .
B1 B 0.5275(6) 0.3596(3) 0.1241(3) 0.0613(12) Uani 1 1 d . . .
B2 B 0.5693(5) 0.1244(2) -0.3680(2) 0.0466(10) Uani 1 1 d . . .
C1 C 0.2433(5) 0.3326(3) 0.2062(3) 0.0850(14) Uani 1 1 d . . .
H1A H 0.2819 0.3816 0.1872 0.128 Uiso 1 1 calc R . .
H1B H 0.2402 0.3416 0.2625 0.128 Uiso 1 1 calc R . .
H1C H 0.1439 0.3170 0.1808 0.128 Uiso 1 1 calc R . .
C2 C 0.3431(5) 0.2665(3) 0.1879(2) 0.0603(10) Uani 1 1 d . . .
C3 C 0.3280(5) 0.1859(3) 0.2033(2) 0.0637(11) Uani 1 1 d . . .
H3B H 0.2504 0.1621 0.2277 0.076 Uiso 1 1 calc R . .
C4 C 0.4467(4) 0.1467(2) 0.1765(2) 0.0535(10) Uani 1 1 d . . .
C5 C 0.4648(5) 0.0579(2) 0.1813(2) 0.0713(12) Uani 1 1 d . . .
H5A H 0.5533 0.0435 0.1578 0.107 Uiso 1 1 calc R . .
H5B H 0.3786 0.0263 0.1534 0.107 Uiso 1 1 calc R . .
H5C H 0.4742 0.0473 0.2357 0.107 Uiso 1 1 calc R . .
C6 C 0.5373(4) 0.2062(2) 0.14452(19) 0.0454(9) Uani 1 1 d . . .
C7 C 0.6741(4) 0.2028(2) 0.11077(18) 0.0431(8) Uani 1 1 d . . .
C8 C 0.7434(4) 0.2703(2) 0.08404(19) 0.0480(9) Uani 1 1 d . . .
C9 C 0.8813(5) 0.2833(2) 0.0497(2) 0.0563(10) Uani 1 1 d . . .
C10 C 0.9941(5) 0.2227(3) 0.0319(3) 0.0798(13) Uani 1 1 d . . .
H10A H 1.0759 0.2488 0.0092 0.120 Uiso 1 1 calc R . .
H10B H 0.9465 0.1787 -0.0047 0.120 Uiso 1 1 calc R . .
H10C H 1.0314 0.2022 0.0801 0.120 Uiso 1 1 calc R . .
C11 C 0.8933(5) 0.3644(3) 0.0361(2) 0.0597(10) Uani 1 1 d . . .
H11A H 0.9720 0.3905 0.0143 0.072 Uiso 1 1 calc R . .
C12 C 0.7670(5) 0.4005(2) 0.0608(2) 0.0597(10) Uani 1 1 d . . .
C13 C 0.7327(6) 0.4867(2) 0.0546(3) 0.0829(14) Uani 1 1 d . . .
H13A H 0.6399 0.4958 0.0761 0.124 Uiso 1 1 calc R . .
H13B H 0.7240 0.4968 0.0000 0.124 Uiso 1 1 calc R . .
H13C H 0.8121 0.5226 0.0836 0.124 Uiso 1 1 calc R . .
C14 C 0.7442(4) 0.1252(2) 0.1030(2) 0.0477(9) Uani 1 1 d . . .
C15 C 0.8595(4) 0.1076(2) 0.1574(2) 0.0496(9) Uani 1 1 d . . .
C16 C 0.9292(5) 0.0364(2) 0.1492(2) 0.0636(11) Uani 1 1 d . . .
H16A H 1.0065 0.0263 0.1864 0.076 Uiso 1 1 calc R . .
C17? C 0.8819(6) -0.0190(3) 0.0851(3) 0.0795(14) Uani 1 1 d . . .
H17A H 0.9266 -0.0676 0.0791 0.095 Uiso 1 1 calc R . .
C18 C 0.7688(6) -0.0034(3) 0.0295(3) 0.0772(14) Uani 1 1 d . . .
H18A H 0.7388 -0.0409 -0.0143 0.093 Uiso 1 1 calc R . .
C19 C 0.7005(5) 0.0674(2) 0.0388(2) 0.0632(11) Uani 1 1 d . . .
H19A H 0.6233 0.0769 0.0013 0.076 Uiso 1 1 calc R . .
C20 C 0.7495(4) 0.1876(2) 0.33799(18) 0.0436(8) Uani 1 1 d . . .
C21 C 0.6962(4) 0.2645(2) 0.34448(18) 0.0423(8) Uani 1 1 d . . .
C22 C 0.5661(4) 0.2774(2) 0.37878(19) 0.0461(9) Uani 1 1 d . . .
H22A H 0.5297 0.3284 0.3825 0.055 Uiso 1 1 calc R . .
C23 C 0.4915(4) 0.2135(2) 0.40717(19) 0.0447(8) Uani 1 1 d . . .
C24 C 0.5394(4) 0.1369(2) 0.4023(2) 0.0510(9) Uani 1 1 d . . .
H24A H 0.4862 0.0944 0.4217 0.061 Uiso 1 1 calc R . .
C25 C 0.6694(4) 0.1254(2) 0.3677(2) 0.0503(9) Uani 1 1 d . . .
H25A H 0.7045 0.0740 0.3641 0.060 Uiso 1 1 calc R . .
C26 C 0.2558(5) 0.1173(3) -0.3102(3) 0.0797(13) Uani 1 1 d . . .
H26A H 0.3109 0.0723 -0.3266 0.120 Uiso 1 1 calc R . .
H26B H 0.1595 0.1125 -0.3408 0.120 Uiso 1 1 calc R . .
H26C H 0.2425 0.1171 -0.2551 0.120 Uiso 1 1 calc R . .
C27 C 0.3402(4) 0.1942(2) -0.3227(2) 0.0557(10) Uani 1 1 d . . .
C28 C 0.3008(4) 0.2732(2) -0.3067(2) 0.0602(10) Uani 1 1 d . . .
H28A H 0.2125 0.2873 -0.2867 0.072 Uiso 1 1 calc R . .
C29 C 0.4123(4) 0.3274(2) -0.3250(2) 0.0491(9) Uani 1 1 d . . .
C30 C 0.4086(5) 0.4178(2) -0.3159(2) 0.0704(12) Uani 1 1 d . . .
H30A H 0.3175 0.4318 -0.2949 0.106 Uiso 1 1 calc R . .
H30B H 0.4126 0.4378 -0.3666 0.106 Uiso 1 1 calc R . .
H30C H 0.4933 0.4418 -0.2805 0.106 Uiso 1 1 calc R . .
C31 C 0.5252(4) 0.27920(19) -0.35334(18) 0.0412(8) Uani 1 1 d . . .
C32 C 0.6629(4) 0.29885(19) -0.38252(18) 0.0401(8) Uani 1 1 d . . .
C33 C 0.7504(4) 0.23861(19) -0.41033(18) 0.0403(8) Uani 1 1 d . . .
C34 C 0.8884(4) 0.2426(2) -0.44590(19) 0.0460(9) Uani 1 1 d . . .
C35 C 0.9791(5) 0.3151(2) -0.4675(2) 0.0607(10) Uani 1 1 d . . .
H35A H 1.0660 0.2978 -0.4908 0.091 Uiso 1 1 calc R . .
H35B H 1.0101 0.3518 -0.4208 0.091 Uiso 1 1 calc R . .
H35C H 0.9191 0.3421 -0.5049 0.091 Uiso 1 1 calc R . .
C36 C 0.9246(4) 0.1643(2) -0.4593(2) 0.0521(9) Uani 1 1 d . . .
H36A H 1.0085 0.1482 -0.4825 0.063 Uiso 1 1 calc R . .
C37 C 0.8159(4) 0.1123(2) -0.4328(2) 0.0482(9) Uani 1 1 d . . .
C38 C 0.8120(5) 0.0227(2) -0.4345(3) 0.0673(11) Uani 1 1 d . . .
H38A H 0.7245 0.0029 -0.4119 0.101 Uiso 1 1 calc R . .
H38B H 0.9004 0.0084 -0.4045 0.101 Uiso 1 1 calc R . .
H38C H 0.8085 -0.0011 -0.4883 0.101 Uiso 1 1 calc R . .
C39 C 0.7178(4) 0.3851(2) -0.38509(19) 0.0433(8) Uani 1 1 d . . .
C40 C 0.8372(4) 0.4236(2) -0.3346(2) 0.0472(9) Uani 1 1 d . . .
C41 C 0.8928(5) 0.5019(2) -0.3387(2) 0.0630(11) Uani 1 1 d . . .
H41A H 0.9733 0.5257 -0.3035 0.076 Uiso 1 1 calc R . .
C42 C 0.8262(5) 0.5451(3) -0.3964(3) 0.0715(12) Uani 1 1 d . . .
H42A H 0.8605 0.5988 -0.3995 0.086 Uiso 1 1 calc R . .
C43 C 0.7104(5) 0.5086(2) -0.4486(2) 0.0706(12) Uani 1 1 d . . .
H43A H 0.6683 0.5370 -0.4883 0.085 Uiso 1 1 calc R . .
C44 C 0.6546(4) 0.4294(2) -0.4430(2) 0.0559(10) Uani 1 1 d . . .
H44A H 0.5742 0.4057 -0.4783 0.067 Uiso 1 1 calc R . .
C45 C 0.7581(4) 0.3353(2) -0.16779(19) 0.0542(10) Uani 1 1 d . . .
C46 C 0.7444(5) 0.2507(2) -0.1658(2) 0.0542(10) Uani 1 1 d . . .
C47 C 0.6223(5) 0.2131(3) -0.1395(2) 0.0696(12) Uani 1 1 d . . .
H47A H 0.6147 0.1574 -0.1369 0.083 Uiso 1 1 calc R . .
C48 C 0.5105(6) 0.2593(4) -0.1169(2) 0.0786(14) Uani 1 1 d . . .
C49 C 0.5163(6) 0.3412(4) -0.1189(3) 0.0838(15) Uani 1 1 d . . .
H49A H 0.4376 0.3706 -0.1040 0.101 Uiso 1 1 calc R . .
C50 C 0.6421(6) 0.3795(3) -0.1438(2) 0.0728(13) Uani 1 1 d . . .
H50A H 0.6493 0.4355 -0.1445 0.087 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'
S S 0.1246 0.1234 '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
O2 S1 O3 120.93(18) . . ?
O2 S1 O1 104.95(16) . . ?
O3 S1 O1 109.03(15) . . ?
O2 S1 C20 108.69(16) . . ?
O3 S1 C20 106.45(17) . . ?
O1 S1 C20 105.92(14) . . ?
O9 S2 O10 120.59(19) . . ?
O9 S2 O8 110.06(16) . . ?
O10 S2 O8 105.07(17) . . ?
O9 S2 C45 107.3(2) . . ?
O10 S2 C45 108.82(19) . . ?
O8 S2 C45 103.76(15) . . ?
C15 O1 S1 125.0(2) . . ?
C40 O8 S2 121.8(2) . . ?
C2 N1 C6 108.0(3) . . ?
C2 N1 B1 125.9(3) . . ?
C6 N1 B1 126.1(3) . . ?
C12 N2 C8 108.5(3) . . ?
C12 N2 B1 126.2(3) . . ?
C8 N2 B1 125.3(3) . . ?
O5 N3 O4 123.9(3) . . ?
O5 N3 C21 118.4(3) . . ?
O4 N3 C21 117.7(3) . . ?
O6 N4 O7 124.4(3) . . ?
O6 N4 C23 118.6(3) . . ?
O7 N4 C23 117.0(3) . . ?
C27 N5 C31 108.3(3) . . ?
C27 N5 B2 125.4(3) . . ?
C31 N5 B2 126.1(3) . . ?
C37 N6 C33 108.3(3) . . ?
C37 N6 B2 126.2(3) . . ?
C33 N6 B2 125.4(3) . . ?
O12 N7 O11 125.4(4) . . ?
O12 N7 C46 118.9(3) . . ?
O11 N7 C46 115.6(4) . . ?
O14 N8 O13 124.7(7) . . ?
O14 N8 C48 118.1(6) . . ?
O13 N8 C48 117.2(6) . . ?
F1 B1 F2 109.7(4) . . ?
F1 B1 N1 110.7(4) . . ?
F2 B1 N1 110.0(4) . . ?
F1 B1 N2 110.0(4) . . ?
F2 B1 N2 109.5(4) . . ?
N1 B1 N2 106.9(3) . . ?
F3 B2 F4 109.0(3) . . ?
F3 B2 N6 110.5(3) . . ?
F4 B2 N6 110.3(3) . . ?
F3 B2 N5 110.9(3) . . ?
F4 B2 N5 109.7(3) . . ?
N6 B2 N5 106.4(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 108.8(3) . . ?
N1 C2 C1 122.3(4) . . ?
C3 C2 C1 128.9(4) . . ?
C4 C3 C2 109.1(4) . . ?
C4 C3 H3B 125.4 . . ?
C2 C3 H3B 125.4 . . ?
C3 C4 C6 106.0(3) . . ?
C3 C4 C5 123.8(4) . . ?
C6 C4 C5 130.3(4) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 C7 119.9(3) . . ?
N1 C6 C4 108.1(3) . . ?
C7 C6 C4 132.0(3) . . ?
C8 C7 C6 121.5(3) . . ?
C8 C7 C14 119.2(3) . . ?
C6 C7 C14 119.3(3) . . ?
C7 C8 N2 120.3(3) . . ?
C7 C8 C9 132.4(3) . . ?
N2 C8 C9 107.3(3) . . ?
C11 C9 C8 106.2(4) . . ?
C11 C9 C10 125.8(4) . . ?
C8 C9 C10 128.0(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 C12 108.6(4) . . ?
C9 C11 H11A 125.7 . . ?
C12 C11 H11A 125.7 . . ?
N2 C12 C11 109.4(3) . . ?
N2 C12 C13 124.3(4) . . ?
C11 C12 C13 126.3(4) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 116.9(3) . . ?
C15 C14 C7 122.1(3) . . ?
C19 C14 C7 121.0(3) . . ?
C16 C15 C14 122.6(3) . . ?
C16 C15 O1 120.8(3) . . ?
C14 C15 O1 116.1(3) . . ?
C17? C16 C15 118.5(4) . . ?
C17? C16 H16A 120.8 . . ?
C15 C16 H16A 120.8 . . ?
C16 C17? C18 120.7(4) . . ?
C16 C17? H17A 119.7 . . ?
C18 C17? H17A 119.7 . . ?
C19 C18 C17? 120.0(4) . . ?
C19 C18 H18A 120.0 . . ?
C17? C18 H18A 120.0 . . ?
C18 C19 C14 121.4(4) . . ?
C18 C19 H19A 119.3 . . ?
C14 C19 H19A 119.3 . . ?
C25 C20 C21 118.2(3) . . ?
C25 C20 S1 116.0(3) . . ?
C21 C20 S1 125.1(3) . . ?
C22 C21 C20 120.6(3) . . ?
C22 C21 N3 115.4(3) . . ?
C20 C21 N3 124.0(3) . . ?
C23 C22 C21 118.6(3) . . ?
C23 C22 H22A 120.7 . . ?
C21 C22 H22A 120.7 . . ?
C22 C23 C24 123.0(3) . . ?
C22 C23 N4 118.6(3) . . ?
C24 C23 N4 118.4(3) . . ?
C23 C24 C25 117.5(3) . . ?
C23 C24 H24A 121.3 . . ?
C25 C24 H24A 121.3 . . ?
C24 C25 C20 122.1(3) . . ?
C24 C25 H25A 118.9 . . ?
C20 C25 H25A 118.9 . . ?
C27 C26 H26A 109.5 . . ?
C27 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C27 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N5 C27 C28 108.3(3) . . ?
N5 C27 C26 123.4(3) . . ?
C28 C27 C26 128.2(4) . . ?
C29 C28 C27 109.8(3) . . ?
C29 C28 H28A 125.1 . . ?
C27 C28 H28A 125.1 . . ?
C28 C29 C31 105.7(3) . . ?
C28 C29 C30 124.9(3) . . ?
C31 C29 C30 129.4(4) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N5 C31 C32 119.3(3) . . ?
N5 C31 C29 107.9(3) . . ?
C32 C31 C29 132.8(3) . . ?
C33 C32 C31 121.2(3) . . ?
C33 C32 C39 118.3(3) . . ?
C31 C32 C39 120.4(3) . . ?
C32 C33 N6 120.6(3) . . ?
C32 C33 C34 131.8(3) . . ?
N6 C33 C34 107.5(3) . . ?
C36 C34 C33 106.1(3) . . ?
C36 C34 C35 124.4(3) . . ?
C33 C34 C35 129.5(3) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 C37 109.4(3) . . ?
C34 C36 H36A 125.3 . . ?
C37 C36 H36A 125.3 . . ?
N6 C37 C36 108.7(3) . . ?
N6 C37 C38 123.8(3) . . ?
C36 C37 C38 127.5(3) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 C44 116.9(3) . . ?
C40 C39 C32 122.9(3) . . ?
C44 C39 C32 120.1(3) . . ?
C41 C40 C39 123.3(3) . . ?
C41 C40 O8 119.3(3) . . ?
C39 C40 O8 116.9(3) . . ?
C40 C41 C42 118.6(4) . . ?
C40 C41 H41A 120.7 . . ?
C42 C41 H41A 120.7 . . ?
C43 C42 C41 119.8(4) . . ?
C43 C42 H42A 120.1 . . ?
C41 C42 H42A 120.1 . . ?
C42 C43 C44 120.7(4) . . ?
C42 C43 H43A 119.6 . . ?
C44 C43 H43A 119.6 . . ?
C43 C44 C39 120.6(4) . . ?
C43 C44 H44A 119.7 . . ?
C39 C44 H44A 119.7 . . ?
C50 C45 C46 118.4(4) . . ?
C50 C45 S2 116.5(3) . . ?
C46 C45 S2 124.8(3) . . ?
C47 C46 C45 121.0(4) . . ?
C47 C46 N7 116.0(4) . . ?
C45 C46 N7 123.0(4) . . ?
C46 C47 C48 118.4(4) . . ?
C46 C47 H47A 120.8 . . ?
C48 C47 H47A 120.8 . . ?
C49 C48 C47 123.2(5) . . ?
C49 C48 N8 118.8(5) . . ?
C47 C48 N8 117.9(5) . . ?
C48 C49 C50 118.3(4) . . ?
C48 C49 H49A 120.9 . . ?
C50 C49 H49A 120.9 . . ?
C49 C50 C45 120.7(4) . . ?
C49 C50 H50A 119.6 . . ?
C45 C50 H50A 119.6 . . ?
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
S1 O2 1.416(3) . ?
S1 O3 1.418(3) . ?
S1 O1 1.568(2) . ?
S1 C20 1.787(4) . ?
S2 O9 1.413(3) . ?
S2 O10 1.421(3) . ?
S2 O8 1.577(2) . ?
S2 C45 1.772(4) . ?
O1 C15 1.416(4) . ?
O4 N3 1.214(4) . ?
O5 N3 1.211(4) . ?
O6 N4 1.207(4) . ?
O7 N4 1.224(4) . ?
O8 C40 1.425(4) . ?
O11 N7 1.229(4) . ?
O12 N7 1.206(4) . ?
O13 N8 1.175(6) . ?
O14 N8 1.157(7) . ?
N1 C2 1.356(5) . ?
N1 C6 1.397(4) . ?
N1 B1 1.536(6) . ?
N2 C12 1.343(5) . ?
N2 C8 1.413(4) . ?
N2 B1 1.547(6) . ?
N3 C21 1.471(4) . ?
N4 C23 1.482(5) . ?
N5 C27 1.361(4) . ?
N5 C31 1.400(4) . ?
N5 B2 1.543(5) . ?
N6 C37 1.353(4) . ?
N6 C33 1.396(4) . ?
N6 B2 1.542(5) . ?
N7 C46 1.469(5) . ?
N8 C48 1.485(7) . ?
F1 B1 1.364(5) . ?
F2 B1 1.388(5) . ?
F3 B2 1.382(4) . ?
F4 B2 1.390(4) . ?
C1 C2 1.497(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.390(6) . ?
C3 C4 1.382(5) . ?
C3 H3B 0.9300 . ?
C4 C6 1.419(5) . ?
C4 C5 1.507(5) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.410(5) . ?
C7 C8 1.382(5) . ?
C7 C14 1.476(5) . ?
C8 C9 1.433(5) . ?
C9 C11 1.389(5) . ?
C9 C10 1.511(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.403(6) . ?
C11 H11A 0.9300 . ?
C12 C13 1.500(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.389(5) . ?
C14 C19 1.391(5) . ?
C15 C16 1.380(5) . ?
C16 C17? 1.372(5) . ?
C16 H16A 0.9300 . ?
C17? C18 1.378(6) . ?
C17? H17A 0.9300 . ?
C18 C19 1.369(5) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 C25 1.382(5) . ?
C20 C21 1.395(5) . ?
C21 C22 1.379(5) . ?
C22 C23 1.368(5) . ?
C22 H22A 0.9300 . ?
C23 C24 1.370(5) . ?
C24 C25 1.377(5) . ?
C24 H24A 0.9300 . ?
C25 H25A 0.9300 . ?
C26 C27 1.482(5) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.394(5) . ?
C28 C29 1.378(5) . ?
C28 H28A 0.9300 . ?
C29 C31 1.430(5) . ?
C29 C30 1.498(5) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C32 1.407(5) . ?
C32 C33 1.393(4) . ?
C32 C39 1.488(5) . ?
C33 C34 1.433(5) . ?
C34 C36 1.369(5) . ?
C34 C35 1.502(5) . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 C37 1.395(5) . ?
C36 H36A 0.9300 . ?
C37 C38 1.484(5) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.383(5) . ?
C39 C44 1.391(5) . ?
C40 C41 1.371(5) . ?
C41 C42 1.390(5) . ?
C41 H41A 0.9300 . ?
C42 C43 1.365(6) . ?
C42 H42A 0.9300 . ?
C43 C44 1.390(5) . ?
C43 H43A 0.9300 . ?
C44 H44A 0.9300 . ?
C45 C50 1.390(6) . ?
C45 C46 1.406(5) . ?
C46 C47 1.360(6) . ?
C47 C48 1.370(6) . ?
C47 H47A 0.9300 . ?
C48 C49 1.362(7) . ?
C49 C50 1.380(7) . ?
C49 H49A 0.9300 . ?
C50 H50A 0.9300 . ?
