#------------------------------------------------------------------------------
#$Date: 2024-10-06 10:09:48 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295193 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/22/1572286.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_1572286
loop_
_publ_author_name
'Hollister, Kimberly K.'
'Molino, Andrew'
'Le, VuongVy V'
'Jones, Nula'
'Smith, Wyatt J.'
'Müller, Peter'
'Dickie, Diane A.'
'Wilson, David J. D.'
'Gilliard, Jr, Robert J'
_publ_section_title
;
 Pentacyclic fused diborepinium ions with carbene- and carbone-mediated
 deep-blue to red emission.
;
_journal_issue                   35
_journal_name_full               'Chemical science'
_journal_page_first              14358
_journal_page_last               14370
_journal_paper_doi               10.1039/d4sc03835e
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C44 H54 B2 N4, 2(C2 F6 N2 O4 S2), 2(C H2 Cl2)'
_chemical_formula_sum            'C50 H58 B2 Cl4 F12 N8 O8 S4'
_chemical_formula_weight         1418.70
_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     dual
_audit_creation_date             2024-03-27
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-03-28 deposited with the CCDC.	2024-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                96.7530(10)
_cell_angle_beta                 92.3660(10)
_cell_angle_gamma                95.8310(10)
_cell_formula_units_Z            1
_cell_length_a                   8.9168(4)
_cell_length_b                   9.3168(4)
_cell_length_c                   18.6398(7)
_cell_measurement_reflns_used    9814
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      27.096
_cell_measurement_theta_min      2.603
_cell_volume                     1527.60(11)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing.cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service V6.2.14'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing.data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing.structure_refinement  'SHELXL--2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing.structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'Photon III'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa four--circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    'one pinhole collimator 0.8 mm'
_diffrn_radiation_monochromator  'HELIOS double bounce multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            40018
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns.reduction_process narrow-frame
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.109
_diffrn_reflns_theta_min         2.214
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.425
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1070 before and 0.0450 after correction.
The Ratio of minimum to maximum transmission is 0.9332.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.504
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.619
_refine_diff_density_min         -1.228
_refine_diff_density_rms         0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.583
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         6729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.583
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0809
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2826
_refine_ls_wR_factor_ref         0.2909
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6064
_reflns_number_total             6729
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc03835e2.cif
_cod_data_source_block           S7
_cod_depositor_comments
'Adding full bibliography for 1572276--1572287.cif.'
_cod_database_code               1572286
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.927
_shelx_estimated_absorpt_t_min   0.814
_computing.bruker_data_scaling
'SADABS--2016/2 -- Bruker AXS area detector scaling and absorption correction'
_olex2_refinement_description
;
1. Others
 Sof(O4A)=1-FVAR(1)
 Sof(O4)=FVAR(1)
 Sof(O3A)=1-FVAR(2)
 Sof(O3)=FVAR(2)
 Sof(F5A)=Sof(F4A)=Sof(F6A)=1-FVAR(3)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(3)
 Sof(F3A)=Sof(F1A)=Sof(F2A)=1-FVAR(4)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(4)
 Sof(O1A)=1-FVAR(5)
 Sof(O1)=FVAR(5)
2.a Ternary CH refined with riding coordinates:
 C13(H13), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C19(H19A,H19B,
 H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
N1 N 0.0661(2) 0.1880(2) 0.29680(11) 0.0183(5) Uani 1 1 d . . . . .
N2 N 0.2290(2) 0.3662(2) 0.27926(11) 0.0196(5) Uani 1 1 d . . . . .
C1 C -0.0154(3) 0.4773(2) 0.42197(13) 0.0164(5) Uani 1 1 d . . . . .
C2 C 0.0819(3) 0.4049(2) 0.46225(13) 0.0171(5) Uani 1 1 d . . . . .
H2 H 0.140169 0.338537 0.436270 0.021 Uiso 1 1 calc R U . . .
C3 C 0.1003(3) 0.4225(2) 0.53793(13) 0.0160(5) Uani 1 1 d . . . . .
C4 C 0.2044(3) 0.3328(3) 0.56732(14) 0.0192(5) Uani 1 1 d . . . . .
H4 H 0.242605 0.265974 0.531990 0.023 Uiso 1 1 calc R U . . .
C5 C 0.2584(3) 0.3259(3) 0.63636(14) 0.0188(5) Uani 1 1 d . . . . .
H5 H 0.326403 0.254475 0.639586 0.023 Uiso 1 1 calc R U . . .
C6 C 0.2331(3) 0.4050(3) 0.70548(13) 0.0185(5) Uani 1 1 d . . . . .
C7 C 0.3195(3) 0.3684(3) 0.76437(14) 0.0216(5) Uani 1 1 d . . . . .
H7 H 0.384024 0.293740 0.756295 0.026 Uiso 1 1 calc R U . . .
C8 C 0.3127(3) 0.4381(3) 0.83325(15) 0.0256(6) Uani 1 1 d . . . . .
H8 H 0.373626 0.412877 0.871883 0.031 Uiso 1 1 calc R U . . .
C9 C 0.2162(3) 0.5460(3) 0.84620(14) 0.0267(6) Uani 1 1 d . . . . .
H9 H 0.212481 0.596095 0.893412 0.032 Uiso 1 1 calc R U . . .
C10 C 0.1264(3) 0.5792(3) 0.78993(14) 0.0228(5) Uani 1 1 d . . . . .
H10 H 0.058919 0.650694 0.799828 0.027 Uiso 1 1 calc R U . . .
C11 C 0.1300(3) 0.5115(3) 0.71778(13) 0.0178(5) Uani 1 1 d . . . . .
C12 C 0.0945(3) 0.3333(3) 0.30608(13) 0.0172(5) Uani 1 1 d . . . . .
C13 C -0.0759(3) 0.1144(3) 0.32091(15) 0.0222(6) Uani 1 1 d . . . . .
H13 H -0.135842 0.193181 0.341319 0.027 Uiso 1 1 calc R U . . .
C14 C -0.0466(3) 0.0250(3) 0.38114(18) 0.0323(7) Uani 1 1 d . . . . .
H14A H -0.002770 -0.062847 0.361758 0.048 Uiso 1 1 calc R U . . .
H14B H -0.141832 -0.002530 0.402930 0.048 Uiso 1 1 calc R U . . .
H14C H 0.023870 0.082145 0.417988 0.048 Uiso 1 1 calc R U . . .
C15 C -0.1716(4) 0.0291(4) 0.25727(18) 0.0367(7) Uani 1 1 d . . . . .
H15A H -0.175480 0.088427 0.217315 0.055 Uiso 1 1 calc R U . . .
H15B H -0.274083 0.004140 0.272242 0.055 Uiso 1 1 calc R U . . .
H15C H -0.126681 -0.060264 0.241329 0.055 Uiso 1 1 calc R U . . .
C16 C 0.1847(3) 0.1273(3) 0.26297(15) 0.0243(6) Uani 1 1 d . . . . .
C17 C 0.1901(4) -0.0319(3) 0.24291(18) 0.0330(7) Uani 1 1 d . . . . .
H17A H 0.162909 -0.083551 0.284171 0.049 Uiso 1 1 calc R U . . .
H17B H 0.292380 -0.049969 0.229666 0.049 Uiso 1 1 calc R U . . .
H17C H 0.118630 -0.066838 0.201715 0.049 Uiso 1 1 calc R U . . .
C18 C 0.2873(3) 0.2387(3) 0.25241(15) 0.0260(6) Uani 1 1 d . . . . .
C19 C 0.4358(4) 0.2369(4) 0.2188(2) 0.0395(8) Uani 1 1 d . . . . .
H19A H 0.435241 0.291134 0.176785 0.059 Uiso 1 1 calc R U . . .
H19B H 0.453766 0.136249 0.203208 0.059 Uiso 1 1 calc R U . . .
H19C H 0.516069 0.282285 0.254170 0.059 Uiso 1 1 calc R U . . .
C20 C 0.3059(3) 0.5122(3) 0.27217(15) 0.0239(6) Uani 1 1 d . . . . .
H20 H 0.416777 0.503413 0.273091 0.029 Uiso 1 1 calc R U . . .
C21 C 0.2630(4) 0.5588(3) 0.19976(17) 0.0333(7) Uani 1 1 d . . . . .
H21A H 0.278306 0.481609 0.161109 0.050 Uiso 1 1 calc R U . . .
H21B H 0.326315 0.647866 0.192823 0.050 Uiso 1 1 calc R U . . .
H21C H 0.156682 0.576966 0.198389 0.050 Uiso 1 1 calc R U . . .
C22 C 0.2794(4) 0.6238(3) 0.33533(17) 0.0307(7) Uani 1 1 d . . . . .
H22A H 0.175815 0.649608 0.330962 0.046 Uiso 1 1 calc R U . . .
H22B H 0.350593 0.711042 0.334965 0.046 Uiso 1 1 calc R U . . .
H22C H 0.294590 0.582824 0.380819 0.046 Uiso 1 1 calc R U . . .
B1 B -0.0217(3) 0.4415(3) 0.33874(15) 0.0165(5) Uani 1 1 d . . . . .
S2 S 0.46584(9) 0.05423(11) 0.43501(5) 0.0430(3) Uani 1 1 d . . . . .
F4 F 0.5270(5) 0.3546(5) 0.4864(2) 0.0378(11) Uani 0.497(6) 1 d . . P A 1
F5 F 0.6156(5) 0.2833(4) 0.3848(2) 0.0390(12) Uani 0.497(6) 1 d . . P A 1
F6 F 0.7213(4) 0.2356(4) 0.4840(3) 0.0334(10) Uani 0.497(6) 1 d . . P A 1
O3 O 0.3129(4) 0.0432(5) 0.4461(3) 0.0341(17) Uani 0.535(10) 1 d . . P B 1
O4 O 0.5515(5) -0.0302(4) 0.4025(2) 0.0309(15) Uani 0.524(9) 1 d . . P B 1
N4 N 0.5633(5) -0.0505(5) 0.4766(2) 0.0712(11) Uani 1 1 d . . . . .
C24 C 0.5706(5) 0.2343(4) 0.44837(18) 0.0434(9) Uani 1 1 d . . . . .
S1 S 0.07083(12) 0.12084(8) 0.04345(5) 0.0429(3) Uani 1 1 d . . . . .
F1 F -0.0387(8) 0.3300(9) -0.0232(5) 0.065(2) Uani 0.480(9) 1 d . . P C 1
F2 F 0.0975(7) 0.2003(5) -0.0893(2) 0.0500(17) Uani 0.480(9) 1 d . . P C 1
F3 F 0.1969(8) 0.3564(7) -0.0022(3) 0.061(2) Uani 0.480(9) 1 d . . P C 1
O1 O 0.2041(6) 0.0582(6) 0.0365(4) 0.049(2) Uani 0.498(13) 1 d . . P D 1
O2 O 0.0013(10) 0.1659(8) 0.1001(3) 0.179(4) Uani 1 1 d . . . . .
N3 N 0.0801(6) -0.0178(5) -0.0072(3) 0.0923(16) Uani 1 1 d . . . . .
C23 C 0.0752(4) 0.2626(4) -0.0153(2) 0.0473(9) Uani 1 1 d . . . . .
Cl1 Cl 0.53833(12) 0.90253(10) 0.11262(5) 0.0493(3) Uani 1 1 d . . . . .
Cl2 Cl 0.40512(13) 0.64527(11) 0.02043(5) 0.0574(3) Uani 1 1 d . . . . .
C25 C 0.4540(5) 0.8329(5) 0.0267(2) 0.0504(9) Uani 1 1 d . . . . .
H25A H 0.362354 0.881415 0.017916 0.060 Uiso 1 1 calc R U . . .
H25B H 0.525126 0.854454 -0.010950 0.060 Uiso 1 1 calc R U . . .
O4A O 0.4976(5) -0.0063(5) 0.3541(2) 0.0291(15) Uani 0.476(9) 1 d . . P B 2
O3A O 0.3303(5) 0.1122(6) 0.4095(3) 0.0289(16) Uani 0.465(10) 1 d . . P B 2
F5A F 0.4800(6) 0.3064(4) 0.4070(2) 0.0551(16) Uani 0.503(6) 1 d . . P A 2
F4A F 0.5413(4) 0.2769(5) 0.5149(2) 0.0345(12) Uani 0.503(6) 1 d . . P A 2
F6A F 0.6966(6) 0.2350(5) 0.4331(4) 0.058(2) Uani 0.503(6) 1 d . . P A 2
F3A F 0.0741(8) 0.3944(5) 0.0342(4) 0.082(3) Uani 0.520(9) 1 d . . P C 2
F1A F -0.0476(8) 0.2497(10) -0.0502(5) 0.081(2) Uani 0.520(9) 1 d . . P C 2
F2A F 0.1862(8) 0.2768(9) -0.0469(5) 0.091(4) Uani 0.520(9) 1 d . . P C 2
O1A O 0.2409(10) 0.1480(9) 0.0771(4) 0.082(3) Uani 0.502(13) 1 d . . P D 2
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'
Cl Cl 0.1484 0.1585 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 1.00 0.00 0.2530
-1.00 1.00 -1.00 0.2560
-1.00 1.00 1.00 0.2250
-1.00 0.00 -1.00 0.1550
-1.00 0.00 0.00 0.1500
-1.00 -1.00 -1.00 0.1350
-1.00 0.00 1.00 0.1380
-1.00 -1.00 0.00 0.1260
-1.00 -1.00 1.00 0.1060
0.00 1.00 0.00 0.2140
0.00 -1.00 0.00 0.0820
0.00 1.00 -1.00 0.2070
0.00 -1.00 1.00 0.0790
0.00 0.00 -1.00 0.0900
0.00 0.00 1.00 0.0350
0.00 1.00 1.00 0.1830
1.00 -1.00 1.00 0.1780
1.00 0.00 0.00 0.1640
1.00 1.00 1.00 0.0870
1.00 0.00 -1.00 0.1630
1.00 1.00 0.00 0.0890
1.00 1.00 -1.00 0.0930
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
C12 N1 C13 121.1(2) . . ?
C12 N1 C16 109.7(2) . . ?
C16 N1 C13 129.2(2) . . ?
C12 N2 C18 109.4(2) . . ?
C12 N2 C20 128.1(2) . . ?
C18 N2 C20 122.3(2) . . ?
C2 C1 C3 116.4(2) . 2_566 ?
C2 C1 B1 117.6(2) . . ?
C3 C1 B1 126.0(2) 2_566 . ?
C1 C2 H2 117.4 . . ?
C1 C2 C3 125.2(2) . . ?
C3 C2 H2 117.4 . . ?
C1 C3 C4 126.5(2) 2_566 . ?
C2 C3 C1 118.4(2) . 2_566 ?
C2 C3 C4 115.0(2) . . ?
C3 C4 H4 113.9 . . ?
C5 C4 C3 132.1(2) . . ?
C5 C4 H4 113.9 . . ?
C4 C5 H5 113.4 . . ?
C4 C5 C6 133.1(2) . . ?
C6 C5 H5 113.4 . . ?
C7 C6 C5 114.7(2) . . ?
C7 C6 C11 119.5(2) . . ?
C11 C6 C5 125.8(2) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.7(2) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.4(2) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 118.5 . . ?
C9 C10 C11 123.1(2) . . ?
C11 C10 H10 118.5 . . ?
C6 C11 B1 126.5(2) . 2_566 ?
C10 C11 C6 116.5(2) . . ?
C10 C11 B1 117.0(2) . 2_566 ?
N1 C12 B1 124.1(2) . . ?
N2 C12 N1 107.2(2) . . ?
N2 C12 B1 128.6(2) . . ?
N1 C13 H13 106.5 . . ?
N1 C13 C14 112.1(2) . . ?
N1 C13 C15 111.5(2) . . ?
C14 C13 H13 106.5 . . ?
C14 C13 C15 113.2(2) . . ?
C15 C13 H13 106.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C17 124.4(2) . . ?
C18 C16 N1 106.8(2) . . ?
C18 C16 C17 128.8(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 C19 123.2(2) . . ?
C16 C18 N2 106.9(2) . . ?
C16 C18 C19 129.9(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 H20 107.0 . . ?
N2 C20 C21 110.6(2) . . ?
N2 C20 C22 112.2(2) . . ?
C21 C20 H20 107.0 . . ?
C21 C20 C22 112.7(2) . . ?
C22 C20 H20 107.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1 B1 C12 116.5(2) . . ?
C11 B1 C1 128.9(2) 2_566 . ?
C11 B1 C12 114.5(2) 2_566 . ?
O3 S2 N4 69.7(3) . 2_656 ?
O3 S2 N4 116.1(3) . . ?
O3 S2 C24 118.1(2) . . ?
O4 S2 O3 133.7(3) . . ?
O4 S2 N4 57.4(3) . . ?
O4 S2 N4 120.8(3) . 2_656 ?
O4 S2 C24 106.5(2) . . ?
N4 S2 N4 63.7(2) . 2_656 ?
N4 S2 C24 106.8(2) . . ?
N4 S2 C24 94.28(19) 2_656 . ?
O4A S2 N4 98.3(2) . . ?
O4A S2 C24 103.6(2) . . ?
O3A S2 N4 156.8(3) . . ?
O3A S2 C24 91.7(2) . . ?
O3A S2 O4A 90.5(3) . . ?
S2 O3 N4 63.1(2) . 2_656 ?
S2 N4 S2 116.3(2) . 2_656 ?
S2 N4 O3 140.0(3) . 2_656 ?
S2 N4 O3 47.2(2) 2_656 2_656 ?
S2 N4 N4 56.3(2) 2_656 2_656 ?
S2 N4 N4 60.1(3) . 2_656 ?
O4 N4 S2 49.1(2) . . ?
O4 N4 S2 164.8(4) . 2_656 ?
O4 N4 O3 145.5(4) . 2_656 ?
O4 N4 N4 109.0(5) . 2_656 ?
N4 N4 O3 93.1(4) 2_656 2_656 ?
F4 C24 S2 126.2(3) . . ?
F4 C24 F5 103.2(4) . . ?
F4 C24 F6 98.9(3) . . ?
F5 C24 S2 113.4(3) . . ?
F5 C24 F6 98.0(4) . . ?
F6 C24 S2 112.8(2) . . ?
F5A C24 S2 99.8(3) . . ?
F4A C24 S2 100.6(3) . . ?
F4A C24 F5A 104.9(4) . . ?
F6A C24 S2 113.6(3) . . ?
F6A C24 F5A 116.3(5) . . ?
F6A C24 F4A 118.9(5) . . ?
O1 S1 N3 58.5(4) . . ?
O1 S1 N3 114.8(3) . 2 ?
O1 S1 C23 107.2(3) . . ?
O2 S1 O1 131.4(4) . . ?
O2 S1 N3 92.5(5) . 2 ?
O2 S1 N3 139.5(5) . . ?
O2 S1 C23 107.0(3) . . ?
O2 S1 O1A 99.2(5) . . ?
N3 S1 N3 57.5(3) . 2 ?
N3 S1 C23 104.5(3) . . ?
N3 S1 C23 99.2(2) 2 . ?
N3 S1 O1A 99.9(4) . . ?
O1A S1 N3 153.7(4) . 2 ?
O1A S1 C23 99.8(3) . . ?
S1 N3 S1 122.5(3) . 2 ?
S1 N3 N3 65.3(4) . 2 ?
O1 N3 S1 168.7(5) . 2 ?
O1 N3 S1 55.9(3) . . ?
O1 N3 N3 119.8(6) . 2 ?
N3 N3 S1 57.2(3) 2 2 ?
F1 C23 S1 120.0(4) . . ?
F1 C23 F2 102.7(5) . . ?
F1 C23 F3 109.5(6) . . ?
F2 C23 S1 109.3(3) . . ?
F3 C23 S1 112.2(4) . . ?
F3 C23 F2 100.9(5) . . ?
F3A C23 S1 103.6(3) . . ?
F1A C23 S1 108.1(4) . . ?
F1A C23 F3A 104.6(6) . . ?
F2A C23 S1 114.4(4) . . ?
F2A C23 F3A 106.4(6) . . ?
F2A C23 F1A 118.2(8) . . ?
Cl1 C25 H25A 109.4 . . ?
Cl1 C25 H25B 109.4 . . ?
Cl2 C25 Cl1 111.3(2) . . ?
Cl2 C25 H25A 109.4 . . ?
Cl2 C25 H25B 109.4 . . ?
H25A C25 H25B 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
N1 C12 1.341(3) . ?
N1 C13 1.490(3) . ?
N1 C16 1.389(3) . ?
N2 C12 1.339(3) . ?
N2 C18 1.392(3) . ?
N2 C20 1.483(3) . ?
C1 C2 1.398(3) . ?
C1 C3 1.424(3) 2_566 ?
C1 B1 1.545(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.402(3) . ?
C3 C4 1.444(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.366(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.445(3) . ?
C6 C7 1.409(3) . ?
C6 C11 1.426(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.375(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.394(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.376(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.420(3) . ?
C11 B1 1.531(4) 2_566 ?
C12 B1 1.607(3) . ?
C13 H13 1.0000 . ?
C13 C14 1.504(4) . ?
C13 C15 1.525(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.493(4) . ?
C16 C18 1.350(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.489(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20 1.0000 . ?
C20 C21 1.511(4) . ?
C20 C22 1.519(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
S2 O3 1.383(4) . ?
S2 O4 1.272(4) . ?
S2 N4 1.682(5) 2_656 ?
S2 N4 1.613(5) . ?
S2 C24 1.820(4) . ?
S2 O4A 1.594(4) . ?
S2 O3A 1.458(5) . ?
F4 C24 1.354(5) . ?
F5 C24 1.379(5) . ?
F6 C24 1.472(6) . ?
O3 N4 1.769(7) 2_656 ?
N4 N4 1.739(8) 2_656 ?
C24 F5A 1.371(6) . ?
C24 F4A 1.302(5) . ?
C24 F6A 1.170(6) . ?
S1 O1 1.381(5) . ?
S1 O2 1.296(4) . ?
S1 N3 1.520(6) . ?
S1 N3 1.642(6) 2 ?
S1 C23 1.811(4) . ?
S1 O1A 1.601(8) . ?
F1 C23 1.259(7) . ?
F2 C23 1.462(6) . ?
F3 C23 1.318(6) . ?
N3 N3 1.526(10) 2 ?
C23 F3A 1.448(6) . ?
C23 F1A 1.237(7) . ?
C23 F2A 1.176(6) . ?
Cl1 C25 1.762(4) . ?
Cl2 C25 1.747(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
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
N1 C12 B1 C1 87.3(3) . . . . ?
N1 C12 B1 C11 -89.5(3) . . . 2_566 ?
N1 C16 C18 N2 -0.7(3) . . . . ?
N1 C16 C18 C19 179.8(3) . . . . ?
N2 C12 B1 C1 -97.3(3) . . . . ?
N2 C12 B1 C11 85.9(3) . . . 2_566 ?
C1 C2 C3 C1 -0.7(4) . . . 2_566 ?
C1 C2 C3 C4 178.4(2) . . . . ?
C1 C3 C4 C5 -5.9(4) 2_566 . . . ?
C2 C1 B1 C11 171.6(2) . . . 2_566 ?
C2 C1 B1 C12 -4.7(3) . . . . ?
C2 C3 C4 C5 175.1(3) . . . . ?
C3 C1 C2 C3 0.7(4) 2_566 . . . ?
C3 C1 B1 C11 -8.2(4) 2_566 . . 2_566 ?
C3 C1 B1 C12 175.5(2) 2_566 . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 C7 -176.6(3) . . . . ?
C4 C5 C6 C11 4.2(4) . . . . ?
C5 C6 C7 C8 177.4(2) . . . . ?
C5 C6 C11 C10 -178.2(2) . . . . ?
C5 C6 C11 B1 2.7(4) . . . 2_566 ?
C6 C7 C8 C9 1.3(4) . . . . ?
C7 C6 C11 C10 2.6(3) . . . . ?
C7 C6 C11 B1 -176.5(2) . . . 2_566 ?
C7 C8 C9 C10 1.3(4) . . . . ?
C8 C9 C10 C11 -2.0(4) . . . . ?
C9 C10 C11 C6 0.0(4) . . . . ?
C9 C10 C11 B1 179.2(2) . . . 2_566 ?
C11 C6 C7 C8 -3.3(4) . . . . ?
C12 N1 C13 C14 -114.5(3) . . . . ?
C12 N1 C13 C15 117.4(3) . . . . ?
C12 N1 C16 C17 -178.9(3) . . . . ?
C12 N1 C16 C18 0.6(3) . . . . ?
C12 N2 C18 C16 0.5(3) . . . . ?
C12 N2 C18 C19 -179.9(3) . . . . ?
C12 N2 C20 C21 -90.1(3) . . . . ?
C12 N2 C20 C22 36.6(4) . . . . ?
C13 N1 C12 N2 -180.0(2) . . . . ?
C13 N1 C12 B1 -3.8(4) . . . . ?
C13 N1 C16 C17 0.7(4) . . . . ?
C13 N1 C16 C18 -179.8(3) . . . . ?
C16 N1 C12 N2 -0.4(3) . . . . ?
C16 N1 C12 B1 175.9(2) . . . . ?
C16 N1 C13 C14 65.9(3) . . . . ?
C16 N1 C13 C15 -62.1(4) . . . . ?
C17 C16 C18 N2 178.8(3) . . . . ?
C17 C16 C18 C19 -0.7(6) . . . . ?
C18 N2 C12 N1 -0.1(3) . . . . ?
C18 N2 C12 B1 -176.1(2) . . . . ?
C18 N2 C20 C21 84.9(3) . . . . ?
C18 N2 C20 C22 -148.3(3) . . . . ?
C20 N2 C12 N1 175.5(2) . . . . ?
C20 N2 C12 B1 -0.5(4) . . . . ?
C20 N2 C18 C16 -175.4(2) . . . . ?
C20 N2 C18 C19 4.2(4) . . . . ?
B1 C1 C2 C3 -179.1(2) . . . . ?
S2 O4 N4 S2 19.0(14) . . . 2_656 ?
S2 O4 N4 O3 -121.9(6) . . . 2_656 ?
S2 O4 N4 N4 5.0(4) . . . 2_656 ?
O3 S2 N4 S2 -47.7(4) . . . 2_656 ?
O3 S2 N4 O3 -101.5(5) . . . 2_656 ?
O3 S2 N4 O4 126.9(3) . . . . ?
O3 S2 N4 N4 -47.7(4) . . . 2_656 ?
O3 S2 C24 F4 19.3(5) . . . . ?
O3 S2 C24 F5 -109.3(4) . . . . ?
O3 S2 C24 F6 140.4(4) . . . . ?
O4 S2 O3 N4 113.7(4) . . . 2_656 ?
O4 S2 N4 S2 -174.5(4) . . . 2_656 ?
O4 S2 N4 O3 131.6(6) . . . 2_656 ?
O4 S2 N4 N4 -174.5(4) . . . 2_656 ?
O4 S2 C24 F4 -173.9(4) . . . . ?
O4 S2 C24 F5 57.5(4) . . . . ?
O4 S2 C24 F6 -52.8(4) . . . . ?
N4 S2 O3 N4 44.9(3) . . . 2_656 ?
N4 S2 N4 S2 -0.001(1) 2_656 . . 2_656 ?
N4 S2 N4 O3 -53.9(4) 2_656 . . 2_656 ?
N4 S2 N4 O4 174.5(4) 2_656 . . . ?
N4 S2 C24 F4 -50.0(4) 2_656 . . . ?
N4 S2 C24 F4 -113.7(4) . . . . ?
N4 S2 C24 F5 -178.6(3) 2_656 . . . ?
N4 S2 C24 F5 117.7(3) . . . . ?
N4 S2 C24 F6 7.3(3) . . . . ?
N4 S2 C24 F6 71.1(3) 2_656 . . . ?
N4 S2 C24 F5A 176.4(3) . . . . ?
N4 S2 C24 F5A -119.8(3) 2_656 . . . ?
N4 S2 C24 F4A -76.3(3) . . . . ?
N4 S2 C24 F4A -12.5(3) 2_656 . . . ?
N4 S2 C24 F6A 115.7(5) 2_656 . . . ?
N4 S2 C24 F6A 52.0(5) . . . . ?
C24 S2 O3 N4 -83.9(3) . . . 2_656 ?
C24 S2 N4 S2 86.4(3) . . . 2_656 ?
C24 S2 N4 O3 32.6(5) . . . 2_656 ?
C24 S2 N4 O4 -99.1(3) . . . . ?
C24 S2 N4 N4 86.4(3) . . . 2_656 ?
S1 O1 N3 S1 -85(2) . . . 2 ?
S1 O1 N3 N3 -14.0(6) . . . 2 ?
O1 S1 N3 S1 166.6(6) . . . 2 ?
O1 S1 N3 N3 166.6(6) . . . 2 ?
O1 S1 C23 F1 174.8(7) . . . . ?
O1 S1 C23 F2 56.7(5) . . . . ?
O1 S1 C23 F3 -54.4(6) . . . . ?
O2 S1 N3 S1 48.3(8) . . . 2 ?
O2 S1 N3 O1 -118.4(6) . . . . ?
O2 S1 N3 N3 48.3(8) . . . 2 ?
O2 S1 C23 F1 -40.3(8) . . . . ?
O2 S1 C23 F2 -158.4(6) . . . . ?
O2 S1 C23 F3 90.5(6) . . . . ?
O2 S1 C23 F3A 28.7(6) . . . . ?
O2 S1 C23 F1A -81.9(7) . . . . ?
O2 S1 C23 F2A 144.1(8) . . . . ?
N3 S1 N3 S1 0.000(0) 2 . . 2 ?
N3 S1 N3 O1 -166.6(6) 2 . . . ?
N3 S1 C23 F1 113.8(7) . . . . ?
N3 S1 C23 F1 55.1(6) 2 . . . ?
N3 S1 C23 F2 -4.3(4) . . . . ?
N3 S1 C23 F2 -63.0(4) 2 . . . ?
N3 S1 C23 F3 -174.1(5) 2 . . . ?
N3 S1 C23 F3 -115.4(5) . . . . ?
N3 S1 C23 F3A -177.2(4) . . . . ?
N3 S1 C23 F3A 124.1(4) 2 . . . ?
N3 S1 C23 F1A 72.2(6) . . . . ?
N3 S1 C23 F1A 13.5(6) 2 . . . ?
N3 S1 C23 F2A -120.4(7) 2 . . . ?
N3 S1 C23 F2A -61.8(7) . . . . ?
C23 S1 N3 S1 -91.8(4) . . . 2 ?
C23 S1 N3 O1 101.6(3) . . . . ?
C23 S1 N3 N3 -91.8(4) . . . 2 ?
O4A S2 N4 S2 -166.6(3) . . . 2_656 ?
O4A S2 N4 N4 -166.6(3) . . . 2_656 ?
O4A S2 C24 F5A 73.2(3) . . . . ?
O4A S2 C24 F4A -179.5(3) . . . . ?
O4A S2 C24 F6A -51.2(5) . . . . ?
O3A S2 N4 S2 -55.3(7) . . . 2_656 ?
O3A S2 N4 N4 -55.3(7) . . . 2_656 ?
O3A S2 C24 F5A -17.7(3) . . . . ?
O3A S2 C24 F4A 89.6(3) . . . . ?
O3A S2 C24 F6A -142.2(5) . . . . ?
O1A S1 N3 S1 165.3(5) . . . 2 ?
O1A S1 N3 N3 165.3(5) . . . 2 ?
O1A S1 C23 F3A -74.2(5) . . . . ?
O1A S1 C23 F1A 175.2(7) . . . . ?
O1A S1 C23 F2A 41.2(8) . . . . ?
