# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_BODIPY-C10
_database_code_depnum_ccdc_archive 'CCDC 1995025'
loop_
_audit_author_name
_audit_author_address
'Andrew White'
;Imperial College London
United Kingdom
;
_audit_update_record             
;
2020-04-06 deposited with the CCDC.	2020-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H31 B F2 N2 O'
_chemical_formula_sum            'C25 H31 B F2 N2 O'
_chemical_formula_weight         424.33

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.9871(4)
_cell_length_b                   15.6608(8)
_cell_length_c                   19.3410(11)
_cell_angle_alpha                74.494(5)
_cell_angle_beta                 87.660(4)
_cell_angle_gamma                76.490(4)
_cell_volume                     2266.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5594
_cell_measurement_theta_min      2.3694
_cell_measurement_theta_max      72.4168

_exptl_crystal_description       'platy needles'
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.698
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) 
(compiled Jan 20 2011,15:58:25) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'OD Xcalibur PX Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 8.2556
_diffrn_reflns_number            15553
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.371
_diffrn_reflns_theta_max         72.567
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             8578
_reflns_number_gt                6241
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0702P)²+0.0529P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8578
_refine_ls_number_parameters     559
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1369
_refine_ls_wR_factor_gt          0.1230
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
B1A B -0.1961(3) 1.08566(14) 0.06726(12) 0.0385(5) Uani 1 1 d . . . . .
F1A F -0.32059(14) 1.13493(7) 0.10333(7) 0.0479(3) Uani 1 1 d . . . . .
F2A F -0.22738(17) 1.12112(9) -0.00541(7) 0.0548(3) Uani 1 1 d . . . . .
N1A N -0.0144(2) 1.08915(10) 0.08844(9) 0.0378(4) Uani 1 1 d . . . . .
C2A C 0.0555(3) 1.16205(13) 0.07086(13) 0.0473(5) Uani 1 1 d . . . . .
H2AA H -0.000470 1.220813 0.042758 0.057 Uiso 1 1 calc R U . . .
C3A C 0.2229(3) 1.13888(13) 0.09998(14) 0.0498(5) Uani 1 1 d . . . . .
H3AA H 0.299001 1.178363 0.095558 0.060 Uiso 1 1 calc R U . . .
C4A C 0.2561(2) 1.04770(13) 0.13631(12) 0.0409(4) Uani 1 1 d . . . . .
H4AA H 0.359930 1.012639 0.161404 0.049 Uiso 1 1 calc R U . . .
C5A C 0.1076(2) 1.01605(12) 0.12939(10) 0.0346(4) Uani 1 1 d . . . . .
C6A C 0.0784(2) 0.92804(11) 0.15018(9) 0.0310(4) Uani 1 1 d . . . . .
C7A C -0.0761(2) 0.91264(11) 0.13040(10) 0.0333(4) Uani 1 1 d . . . . .
C8A C -0.1415(2) 0.83308(13) 0.14582(11) 0.0404(4) Uani 1 1 d . . . . .
H8AA H -0.083301 0.773845 0.172279 0.048 Uiso 1 1 calc R U . . .
C9A C -0.3047(3) 0.85711(14) 0.11551(13) 0.0475(5) Uani 1 1 d . . . . .
H9AA H -0.379954 0.817814 0.117109 0.057 Uiso 1 1 calc R U . . .
C10A C -0.3381(3) 0.95041(14) 0.08197(12) 0.0444(5) Uani 1 1 d . . . . .
H10A H -0.441832 0.985171 0.056680 0.053 Uiso 1 1 calc R U . . .
N11A N -0.20257(19) 0.98389(10) 0.09060(8) 0.0353(3) Uani 1 1 d . . . . .
C12A C 0.2117(2) 0.85117(11) 0.19185(10) 0.0315(4) Uani 1 1 d . . . . .
C13A C 0.2848(2) 0.85508(12) 0.25460(11) 0.0365(4) Uani 1 1 d . . . . .
H13A H 0.251013 0.909080 0.270223 0.044 Uiso 1 1 calc R U . . .
C14A C 0.4064(2) 0.78163(12) 0.29508(11) 0.0382(4) Uani 1 1 d . . . . .
H14A H 0.453321 0.784605 0.338493 0.046 Uiso 1 1 calc R U . . .
C15A C 0.4579(2) 0.70382(11) 0.27071(10) 0.0350(4) Uani 1 1 d . . . . .
C16A C 0.3888(2) 0.69926(12) 0.20758(10) 0.0356(4) Uani 1 1 d . . . . .
H16A H 0.426140 0.646105 0.191057 0.043 Uiso 1 1 calc R U . . .
C17A C 0.2659(2) 0.77185(11) 0.16871(10) 0.0336(4) Uani 1 1 d . . . . .
H17A H 0.217619 0.767992 0.125870 0.040 Uiso 1 1 calc R U . . .
O18A O 0.57918(18) 0.62763(9) 0.30469(8) 0.0461(3) Uani 1 1 d . . . . .
C19A C 0.6181(2) 0.61099(12) 0.37887(11) 0.0391(4) Uani 1 1 d . . . . .
H19A H 0.511660 0.614662 0.407097 0.047 Uiso 1 1 calc R U . . .
H19B H 0.679899 0.655587 0.386836 0.047 Uiso 1 1 calc R U . . .
C20A C 0.7313(3) 0.51565(12) 0.39956(11) 0.0410(4) Uani 1 1 d . . . . .
H20A H 0.839099 0.516061 0.372477 0.049 Uiso 1 1 calc R U . . .
H20B H 0.672007 0.475058 0.383635 0.049 Uiso 1 1 calc R U . . .
C21A C 0.7791(2) 0.47438(13) 0.47852(11) 0.0407(4) Uani 1 1 d . . . . .
H21A H 0.673235 0.470777 0.506550 0.049 Uiso 1 1 calc R U . . .
H21B H 0.839103 0.513730 0.495672 0.049 Uiso 1 1 calc R U . . .
C22A C 0.8959(3) 0.37916(13) 0.49022(12) 0.0427(4) Uani 1 1 d . . . . .
H22A H 0.836657 0.342493 0.469504 0.051 Uiso 1 1 calc R U . . .
H22B H 1.001845 0.384726 0.462654 0.051 Uiso 1 1 calc R U . . .
C23A C 0.9492(3) 0.32647(13) 0.56731(12) 0.0429(4) Uani 1 1 d . . . . .
H23A H 0.845637 0.315015 0.594729 0.051 Uiso 1 1 calc R U . . .
H23B H 1.003058 0.363516 0.589899 0.051 Uiso 1 1 calc R U . . .
C24A C 1.0763(3) 0.23562(13) 0.57079(12) 0.0439(5) Uani 1 1 d . . . . .
H24A H 1.023861 0.201093 0.545122 0.053 Uiso 1 1 calc R U . . .
H24B H 1.180995 0.248196 0.544860 0.053 Uiso 1 1 calc R U . . .
C25A C 1.1297(3) 0.17593(13) 0.64586(11) 0.0430(4) Uani 1 1 d . . . . .
H25A H 1.025719 0.162021 0.671773 0.052 Uiso 1 1 calc R U . . .
H25B H 1.181396 0.210238 0.671973 0.052 Uiso 1 1 calc R U . . .
C26A C 1.2578(3) 0.08700(13) 0.64672(11) 0.0417(4) Uani 1 1 d . . . . .
H26A H 1.208501 0.055007 0.617768 0.050 Uiso 1 1 calc R U . . .
H26B H 1.363841 0.101408 0.623042 0.050 Uiso 1 1 calc R U . . .
C27A C 1.3069(3) 0.02287(13) 0.72026(12) 0.0466(5) Uani 1 1 d . . . . .
H27A H 1.202243 0.005547 0.743133 0.056 Uiso 1 1 calc R U . . .
H27B H 1.351518 0.055422 0.750150 0.056 Uiso 1 1 calc R U . . .
C28A C 1.4410(3) -0.06287(14) 0.71934(13) 0.0489(5) Uani 1 1 d . . . . .
H28A H 1.466609 -0.101100 0.768557 0.073 Uiso 1 1 calc R U . . .
H28B H 1.396969 -0.096488 0.690915 0.073 Uiso 1 1 calc R U . . .
H28C H 1.546420 -0.046554 0.697939 0.073 Uiso 1 1 calc R U . . .
B1B B 0.2568(3) 0.58577(13) 0.04687(11) 0.0344(4) Uani 1 1 d . . . . .
F1B F 0.21631(15) 0.60853(7) -0.02548(6) 0.0442(3) Uani 1 1 d . . . . .
F2B F 0.13568(14) 0.64172(7) 0.07899(7) 0.0434(3) Uani 1 1 d . . . . .
N1B N 0.25672(18) 0.48436(10) 0.08302(8) 0.0322(3) Uani 1 1 d . . . . .
C2B C 0.1229(2) 0.44564(13) 0.08498(11) 0.0381(4) Uani 1 1 d . . . . .
H2BA H 0.017628 0.473935 0.058669 0.046 Uiso 1 1 calc R U . . .
C3B C 0.1601(2) 0.35800(13) 0.13110(12) 0.0417(4) Uani 1 1 d . . . . .
H3BA H 0.086658 0.316633 0.141304 0.050 Uiso 1 1 calc R U . . .
C4B C 0.3239(2) 0.34277(12) 0.15909(11) 0.0371(4) Uani 1 1 d . . . . .
H4BA H 0.384034 0.288969 0.192444 0.044 Uiso 1 1 calc R U . . .
C5B C 0.3857(2) 0.42218(11) 0.12889(10) 0.0313(4) Uani 1 1 d . . . . .
C6B C 0.5387(2) 0.44520(11) 0.14183(9) 0.0299(3) Uani 1 1 d . . . . .
C7B C 0.5642(2) 0.53187(11) 0.10724(10) 0.0311(4) Uani 1 1 d . . . . .
C8B C 0.7096(2) 0.56907(12) 0.10595(11) 0.0357(4) Uani 1 1 d . . . . .
H8BA H 0.813275 0.540968 0.133432 0.043 Uiso 1 1 calc R U . . .
C9B C 0.6731(3) 0.65393(12) 0.05728(12) 0.0410(4) Uani 1 1 d . . . . .
H9BA H 0.747079 0.694936 0.044761 0.049 Uiso 1 1 calc R U . . .
C10B C 0.5074(3) 0.66787(12) 0.03011(11) 0.0393(4) Uani 1 1 d . . . . .
H10B H 0.449700 0.721074 -0.004527 0.047 Uiso 1 1 calc R U . . .
N11B N 0.44006(19) 0.59556(9) 0.05968(8) 0.0327(3) Uani 1 1 d . . . . .
C12B C 0.6699(2) 0.37882(11) 0.19263(10) 0.0321(4) Uani 1 1 d . . . . .
C13B C 0.7274(2) 0.28906(11) 0.18823(10) 0.0333(4) Uani 1 1 d . . . . .
H13B H 0.685155 0.271121 0.150403 0.040 Uiso 1 1 calc R U . . .
C14B C 0.8448(2) 0.22577(12) 0.23805(10) 0.0352(4) Uani 1 1 d . . . . .
H14B H 0.883474 0.165186 0.234012 0.042 Uiso 1 1 calc R U . . .
C15B C 0.9057(2) 0.25120(12) 0.29377(11) 0.0378(4) Uani 1 1 d . . . . .
C16B C 0.8518(2) 0.34111(12) 0.29790(11) 0.0399(4) Uani 1 1 d . . . . .
H16B H 0.895110 0.359063 0.335486 0.048 Uiso 1 1 calc R U . . .
C17B C 0.7364(2) 0.40384(12) 0.24796(11) 0.0369(4) Uani 1 1 d . . . . .
H17B H 0.701579 0.464943 0.251136 0.044 Uiso 1 1 calc R U . . .
O18B O 1.01701(19) 0.19486(9) 0.34703(8) 0.0481(4) Uani 1 1 d . . . . .
C19B C 1.0647(3) 0.09983(12) 0.35116(12) 0.0415(4) Uani 1 1 d . . . . .
H19C H 1.132626 0.089435 0.308965 0.050 Uiso 1 1 calc R U . . .
H19D H 0.960753 0.075347 0.352292 0.050 Uiso 1 1 calc R U . . .
C20B C 1.1709(3) 0.05370(13) 0.41909(12) 0.0445(5) Uani 1 1 d . . . . .
H20C H 1.101754 0.066573 0.460331 0.053 Uiso 1 1 calc R U . . .
H20D H 1.272815 0.080064 0.417144 0.053 Uiso 1 1 calc R U . . .
C21B C 1.2316(3) -0.04885(13) 0.43166(12) 0.0425(4) Uani 1 1 d . . . . .
H21C H 1.129773 -0.075288 0.433656 0.051 Uiso 1 1 calc R U . . .
H21D H 1.300891 -0.061795 0.390471 0.051 Uiso 1 1 calc R U . . .
C22B C 1.3381(3) -0.09470(13) 0.49994(12) 0.0464(5) Uani 1 1 d . . . . .
H22C H 1.267284 -0.082428 0.540966 0.056 Uiso 1 1 calc R U . . .
H22D H 1.437587 -0.066609 0.498263 0.056 Uiso 1 1 calc R U . . .
C23B C 1.4048(3) -0.19660(13) 0.51373(12) 0.0459(5) Uani 1 1 d . . . . .
H23C H 1.305118 -0.224772 0.516273 0.055 Uiso 1 1 calc R U . . .
H23D H 1.473745 -0.208900 0.472278 0.055 Uiso 1 1 calc R U . . .
C24B C 1.5138(3) -0.24236(13) 0.58125(12) 0.0450(5) Uani 1 1 d . . . . .
H24C H 1.443197 -0.232731 0.622968 0.054 Uiso 1 1 calc R U . . .
H24D H 1.610590 -0.212350 0.579829 0.054 Uiso 1 1 calc R U . . .
C25B C 1.5867(3) -0.34352(13) 0.59273(12) 0.0431(4) Uani 1 1 d . . . . .
H25C H 1.489904 -0.373474 0.593867 0.052 Uiso 1 1 calc R U . . .
H25D H 1.657791 -0.353117 0.551135 0.052 Uiso 1 1 calc R U . . .
C26B C 1.6950(3) -0.38948(13) 0.66046(11) 0.0416(4) Uani 1 1 d . . . . .
H26C H 1.623611 -0.380041 0.702042 0.050 Uiso 1 1 calc R U . . .
H26D H 1.791334 -0.359287 0.659401 0.050 Uiso 1 1 calc R U . . .
C27B C 1.7686(3) -0.49039(13) 0.67203(13) 0.0506(5) Uani 1 1 d . . . . .
H27C H 1.837401 -0.500180 0.629912 0.061 Uiso 1 1 calc R U . . .
H27E H 1.672333 -0.521055 0.674756 0.061 Uiso 1 1 calc R U . . .
C28B C 1.8813(3) -0.53474(14) 0.73928(12) 0.0500(5) Uani 1 1 d . . . . .
H28G H 1.924189 -0.599834 0.743142 0.075 Uiso 1 1 calc R U . . .
H28D H 1.978963 -0.506044 0.736591 0.075 Uiso 1 1 calc R U . . .
H28E H 1.813660 -0.526949 0.781499 0.075 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
B1A F2A 1.376(3) . ?
B1A F1A 1.394(2) . ?
B1A N1A 1.541(3) . ?
B1A N11A 1.549(3) . ?
N1A C2A 1.344(3) . ?
N1A C5A 1.394(2) . ?
C2A C3A 1.400(3) . ?
C3A C4A 1.380(3) . ?
C4A C5A 1.412(3) . ?
C5A C6A 1.401(2) . ?
C6A C7A 1.398(3) . ?
C6A C12A 1.478(2) . ?
C7A N11A 1.391(2) . ?
C7A C8A 1.416(3) . ?
C8A C9A 1.378(3) . ?
C9A C10A 1.397(3) . ?
C10A N11A 1.342(3) . ?
C12A C13A 1.390(3) . ?
C12A C17A 1.400(2) . ?
C13A C14A 1.392(3) . ?
C14A C15A 1.390(3) . ?
C15A O18A 1.374(2) . ?
C15A C16A 1.386(3) . ?
C16A C17A 1.380(2) . ?
O18A C19A 1.422(2) . ?
C19A C20A 1.512(3) . ?
C20A C21A 1.517(3) . ?
C21A C22A 1.527(3) . ?
C22A C23A 1.522(3) . ?
C23A C24A 1.529(3) . ?
C24A C25A 1.517(3) . ?
C25A C26A 1.520(3) . ?
C26A C27A 1.511(3) . ?
C27A C28A 1.513(3) . ?
B1B F1B 1.381(2) . ?
B1B F2B 1.391(2) . ?
B1B N11B 1.543(3) . ?
B1B N1B 1.555(2) . ?
N1B C2B 1.341(2) . ?
N1B C5B 1.393(2) . ?
C2B C3B 1.394(3) . ?
C3B C4B 1.380(3) . ?
C4B C5B 1.417(3) . ?
C5B C6B 1.402(2) . ?
C6B C7B 1.401(2) . ?
C6B C12B 1.474(2) . ?
C7B N11B 1.395(2) . ?
C7B C8B 1.413(3) . ?
C8B C9B 1.382(3) . ?
C9B C10B 1.392(3) . ?
C10B N11B 1.346(2) . ?
C12B C17B 1.396(3) . ?
C12B C13B 1.398(2) . ?
C13B C14B 1.385(3) . ?
C14B C15B 1.385(3) . ?
C15B O18B 1.361(2) . ?
C15B C16B 1.396(3) . ?
C16B C17B 1.374(3) . ?
O18B C19B 1.429(2) . ?
C19B C20B 1.505(3) . ?
C20B C21B 1.520(3) . ?
C21B C22B 1.511(3) . ?
C22B C23B 1.513(3) . ?
C23B C24B 1.509(3) . ?
C24B C25B 1.513(3) . ?
C25B C26B 1.510(3) . ?
C26B C27B 1.510(3) . ?
C27B C28B 1.518(3) . ?

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
F2A B1A F1A 108.67(16) . . ?
F2A B1A N1A 111.30(17) . . ?
F1A B1A N1A 110.35(17) . . ?
F2A B1A N11A 110.78(18) . . ?
F1A B1A N11A 109.66(16) . . ?
N1A B1A N11A 106.07(14) . . ?
C2A N1A C5A 107.77(16) . . ?
C2A N1A B1A 126.68(16) . . ?
C5A N1A B1A 125.56(15) . . ?
N1A C2A C3A 110.17(17) . . ?
C4A C3A C2A 106.89(18) . . ?
C3A C4A C5A 107.52(18) . . ?
N1A C5A C6A 121.19(17) . . ?
N1A C5A C4A 107.66(16) . . ?
C6A C5A C4A 130.82(17) . . ?
C7A C6A C5A 119.87(16) . . ?
C7A C6A C12A 119.94(15) . . ?
C5A C6A C12A 120.18(16) . . ?
N11A C7A C6A 120.84(15) . . ?
N11A C7A C8A 107.28(16) . . ?
C6A C7A C8A 131.82(17) . . ?
C9A C8A C7A 107.65(17) . . ?
C8A C9A C10A 106.78(18) . . ?
N11A C10A C9A 110.28(18) . . ?
C10A N11A C7A 108.01(16) . . ?
C10A N11A B1A 125.74(16) . . ?
C7A N11A B1A 125.96(16) . . ?
C13A C12A C17A 118.53(16) . . ?
C13A C12A C6A 121.44(16) . . ?
C17A C12A C6A 120.03(16) . . ?
C12A C13A C14A 121.46(17) . . ?
C15A C14A C13A 118.70(18) . . ?
O18A C15A C16A 114.86(16) . . ?
O18A C15A C14A 124.45(17) . . ?
C16A C15A C14A 120.68(16) . . ?
C17A C16A C15A 120.05(16) . . ?
C16A C17A C12A 120.56(17) . . ?
C15A O18A C19A 119.82(15) . . ?
O18A C19A C20A 104.50(16) . . ?
C19A C20A C21A 116.84(17) . . ?
C20A C21A C22A 110.35(17) . . ?
C23A C22A C21A 116.95(18) . . ?
C22A C23A C24A 111.43(18) . . ?
C25A C24A C23A 115.24(18) . . ?
C24A C25A C26A 113.41(18) . . ?
C27A C26A C25A 115.31(18) . . ?
C26A C27A C28A 113.86(19) . . ?
F1B B1B F2B 108.59(15) . . ?
F1B B1B N11B 111.35(16) . . ?
F2B B1B N11B 110.50(16) . . ?
F1B B1B N1B 111.10(16) . . ?
F2B B1B N1B 109.60(15) . . ?
N11B B1B N1B 105.69(14) . . ?
C2B N1B C5B 107.78(15) . . ?
C2B N1B B1B 126.03(15) . . ?
C5B N1B B1B 125.41(15) . . ?
N1B C2B C3B 110.40(16) . . ?
C4B C3B C2B 106.98(17) . . ?
C3B C4B C5B 107.34(17) . . ?
N1B C5B C6B 121.27(15) . . ?
N1B C5B C4B 107.50(15) . . ?
C6B C5B C4B 131.09(16) . . ?
C7B C6B C5B 119.59(16) . . ?
C7B C6B C12B 120.55(16) . . ?
C5B C6B C12B 119.84(15) . . ?
N11B C7B C6B 121.05(16) . . ?
N11B C7B C8B 107.85(15) . . ?
C6B C7B C8B 130.84(16) . . ?
C9B C8B C7B 107.30(17) . . ?
C8B C9B C10B 106.94(17) . . ?
N11B C10B C9B 110.62(16) . . ?
C10B N11B C7B 107.29(15) . . ?
C10B N11B B1B 126.92(15) . . ?
C7B N11B B1B 125.72(14) . . ?
C17B C12B C13B 118.24(16) . . ?
C17B C12B C6B 120.37(15) . . ?
C13B C12B C6B 121.36(16) . . ?
C14B C13B C12B 121.19(18) . . ?
C15B C14B C13B 119.73(16) . . ?
O18B C15B C14B 125.27(16) . . ?
O18B C15B C16B 115.16(18) . . ?
C14B C15B C16B 119.57(17) . . ?
C17B C16B C15B 120.45(19) . . ?
C16B C17B C12B 120.78(17) . . ?
C15B O18B C19B 118.81(16) . . ?
O18B C19B C20B 107.02(17) . . ?
C19B C20B C21B 113.54(18) . . ?
C22B C21B C20B 113.25(18) . . ?
C21B C22B C23B 115.06(19) . . ?
C24B C23B C22B 115.19(19) . . ?
C23B C24B C25B 114.73(18) . . ?
C26B C25B C24B 114.78(18) . . ?
C25B C26B C27B 115.00(18) . . ?
C26B C27B C28B 114.16(19) . . ?

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.044

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Cy3_CHTf2
_database_code_depnum_ccdc_archive 'CCDC 1995227'
loop_
_audit_author_name
_audit_author_address
'David Pugh'
;Kings College London
United Kingdom
;
_audit_update_record             
;
2020-04-06 deposited with the CCDC.	2020-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N2 S2, C3 H F6 O4 S2'
_chemical_formula_sum            'C24 H22 F6 N2 O4 S4'
_chemical_formula_weight         644.67

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   13.7964(7)
_cell_length_b                   14.4462(6)
_cell_length_c                   14.8908(7)
_cell_angle_alpha                103.965(4)
_cell_angle_beta                 99.568(4)
_cell_angle_gamma                104.025(4)
_cell_volume                     2713.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    172(4)
_cell_measurement_reflns_used    6083
_cell_measurement_theta_min      3.8100
_cell_measurement_theta_max      72.9070

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_F_000             1320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.921
_shelx_estimated_absorpt_T_min   0.508
_shelx_estimated_absorpt_T_max   0.695
_exptl_absorpt_correction_T_min  0.91927
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.772
_oxdiff_exptl_absorpt_empirical_full_max 1.215
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      172(4)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.4115
_diffrn_reflns_number            16043
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.299
_diffrn_reflns_theta_max         73.365
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             10314
_reflns_number_gt                7939
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'Olex-2, WinGX'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3, Mercury'
_computing_publication_material  ?
_refine_special_details          
;
Two of the CF3 groups were disordered over two sites and this was 
successfully modelled with the aid of DFIX and ISOR restraints. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0893P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10314
_refine_ls_number_parameters     790
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1511
_refine_ls_wR_factor_gt          0.1364
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001

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
C1 C 0.6737(2) 0.0573(2) 0.5963(2) 0.0292(6) Uani 1 1 d . . . . .
C2 C 0.7611(2) 0.0272(3) 0.5874(2) 0.0381(7) Uani 1 1 d . . . . .
H2 H 0.808570 0.057014 0.555610 0.046 Uiso 1 1 calc R U . . .
C3 C 0.7768(3) -0.0481(3) 0.6265(3) 0.0416(7) Uani 1 1 d . . . . .
H3 H 0.835957 -0.069892 0.621605 0.050 Uiso 1 1 calc R U . . .
C4 C 0.7068(3) -0.0914(2) 0.6724(2) 0.0350(6) Uani 1 1 d . . . . .
H4 H 0.719613 -0.141936 0.699205 0.042 Uiso 1 1 calc R U . . .
C5 C 0.6188(2) -0.0633(2) 0.6804(2) 0.0309(6) Uani 1 1 d . . . . .
H5 H 0.570905 -0.094116 0.711218 0.037 Uiso 1 1 calc R U . . .
C6 C 0.6032(2) 0.0123(2) 0.64150(19) 0.0274(6) Uani 1 1 d . . . . .
C7 C 0.5252(2) 0.1271(2) 0.6024(2) 0.0273(5) Uani 1 1 d . . . . .
C8 C 0.4341(2) 0.0121(2) 0.6826(2) 0.0305(6) Uani 1 1 d . . . . .
H8A H 0.419768 -0.061210 0.667995 0.037 Uiso 1 1 calc R U . . .
H8B H 0.371720 0.025556 0.651937 0.037 Uiso 1 1 calc R U . . .
C9 C 0.4567(3) 0.0578(3) 0.7889(2) 0.0449(8) Uani 1 1 d . . . . .
H9A H 0.517084 0.042702 0.819649 0.067 Uiso 1 1 calc R U . . .
H9B H 0.397320 0.030126 0.812484 0.067 Uiso 1 1 calc R U . . .
H9C H 0.470523 0.130317 0.803580 0.067 Uiso 1 1 calc R U . . .
C10 C 0.4535(2) 0.1806(2) 0.5967(2) 0.0312(6) Uani 1 1 d . . . . .
H10 H 0.402276 0.172040 0.631941 0.037 Uiso 1 1 calc R U . . .
C11 C 0.4544(2) 0.2457(2) 0.5418(2) 0.0300(6) Uani 1 1 d . . . . .
H11 H 0.503734 0.250679 0.504293 0.036 Uiso 1 1 calc R U . . .
C12 C 0.3886(2) 0.3037(2) 0.5376(2) 0.0314(6) Uani 1 1 d . . . . .
H12 H 0.342627 0.303497 0.578541 0.038 Uiso 1 1 calc R U . . .
C13 C 0.3867(2) 0.3627(2) 0.4762(2) 0.0295(6) Uani 1 1 d . . . . .
C14 C 0.4093(2) 0.4504(2) 0.3521(2) 0.0320(6) Uani 1 1 d . . . . .
C15 C 0.4311(3) 0.4928(3) 0.2804(3) 0.0425(8) Uani 1 1 d . . . . .
H15 H 0.479320 0.475968 0.245521 0.051 Uiso 1 1 calc R U . . .
C16 C 0.3803(3) 0.5602(3) 0.2615(3) 0.0466(8) Uani 1 1 d . . . . .
H16 H 0.393303 0.589509 0.212370 0.056 Uiso 1 1 calc R U . . .
C17 C 0.3110(3) 0.5856(3) 0.3128(3) 0.0454(8) Uani 1 1 d . . . . .
H17 H 0.276742 0.631453 0.297632 0.055 Uiso 1 1 calc R U . . .
C18 C 0.2903(3) 0.5456(2) 0.3860(2) 0.0385(7) Uani 1 1 d . . . . .
H18 H 0.243872 0.564552 0.422092 0.046 Uiso 1 1 calc R U . . .
C19 C 0.3405(2) 0.4765(2) 0.4043(2) 0.0326(6) Uani 1 1 d . . . . .
C20 C 0.2615(3) 0.4441(3) 0.5375(2) 0.0424(8) Uani 1 1 d . . . . .
H20A H 0.265742 0.515796 0.557173 0.051 Uiso 1 1 calc R U . . .
H20B H 0.283532 0.425254 0.595546 0.051 Uiso 1 1 calc R U . . .
C21 C 0.1515(3) 0.3829(4) 0.4882(3) 0.0621(11) Uani 1 1 d . . . . .
H21A H 0.129521 0.401833 0.430959 0.093 Uiso 1 1 calc R U . . .
H21B H 0.106774 0.395515 0.531597 0.093 Uiso 1 1 calc R U . . .
H21C H 0.146913 0.311861 0.470261 0.093 Uiso 1 1 calc R U . . .
C22 C -0.1765(2) 0.4336(2) 0.92172(19) 0.0281(6) Uani 1 1 d . . . . .
C23 C -0.2596(2) 0.3732(2) 0.9426(2) 0.0341(6) Uani 1 1 d . . . . .
H23 H -0.298309 0.401172 0.982914 0.041 Uiso 1 1 calc R U . . .
C24 C -0.2841(3) 0.2711(2) 0.9027(2) 0.0388(7) Uani 1 1 d . . . . .
H24 H -0.340243 0.228032 0.915923 0.047 Uiso 1 1 calc R U . . .
C25 C -0.2269(3) 0.2306(2) 0.8432(2) 0.0386(7) Uani 1 1 d . . . . .
H25 H -0.245227 0.160234 0.816224 0.046 Uiso 1 1 calc R U . . .
C26 C -0.1443(3) 0.2906(2) 0.8228(2) 0.0341(6) Uani 1 1 d . . . . .
H26 H -0.105808 0.262547 0.782365 0.041 Uiso 1 1 calc R U . . .
C27 C -0.1189(2) 0.3938(2) 0.86323(19) 0.0280(6) Uani 1 1 d . . . . .
C28 C -0.0343(2) 0.5623(2) 0.89735(19) 0.0266(5) Uani 1 1 d . . . . .
C29 C 0.0329(3) 0.4416(2) 0.7950(2) 0.0369(7) Uani 1 1 d . . . . .
H29A H 0.043143 0.377386 0.800180 0.044 Uiso 1 1 calc R U . . .
H29B H 0.100178 0.493670 0.820822 0.044 Uiso 1 1 calc R U . . .
C30 C -0.0062(4) 0.4329(4) 0.6911(3) 0.0631(12) Uani 1 1 d . . . . .
H30A H -0.069973 0.377676 0.663985 0.095 Uiso 1 1 calc R U . . .
H30B H 0.045739 0.420091 0.656074 0.095 Uiso 1 1 calc R U . . .
H30C H -0.019455 0.495288 0.686029 0.095 Uiso 1 1 calc R U . . .
C31 C 0.0384(2) 0.6478(2) 0.8967(2) 0.0281(6) Uani 1 1 d . . . . .
H31 H 0.084607 0.641480 0.856397 0.034 Uiso 1 1 calc R U . . .
C32 C 0.0454(2) 0.7420(2) 0.95308(19) 0.0270(5) Uani 1 1 d . . . . .
H32 H -0.001689 0.746059 0.992695 0.032 Uiso 1 1 calc R U . . .
C33 C 0.1154(2) 0.8311(2) 0.9567(2) 0.0283(6) Uani 1 1 d . . . . .
H33 H 0.162298 0.829945 0.916714 0.034 Uiso 1 1 calc R U . . .
C34 C 0.1180(2) 0.9222(2) 1.0180(2) 0.0269(5) Uani 1 1 d . . . . .
C35 C 0.0907(2) 1.0604(2) 1.1387(2) 0.0315(6) Uani 1 1 d . . . . .
C36 C 0.0634(3) 1.1273(3) 1.2066(2) 0.0381(7) Uani 1 1 d . . . . .
H36 H 0.011301 1.104834 1.237431 0.046 Uiso 1 1 calc R U . . .
C37 C 0.1148(3) 1.2282(3) 1.2279(2) 0.0421(8) Uani 1 1 d . . . . .
H37 H 0.097611 1.275687 1.273987 0.051 Uiso 1 1 calc R U . . .
C38 C 0.1912(3) 1.2605(2) 1.1824(2) 0.0433(8) Uani 1 1 d . . . . .
H38 H 0.225497 1.329824 1.198309 0.052 Uiso 1 1 calc R U . . .
C39 C 0.2186(3) 1.1933(2) 1.1139(2) 0.0394(7) Uani 1 1 d . . . . .
H39 H 0.271109 1.215704 1.083397 0.047 Uiso 1 1 calc R U . . .
C40 C 0.1659(2) 1.0920(2) 1.0920(2) 0.0308(6) Uani 1 1 d . . . . .
C41 C 0.2567(3) 1.0280(2) 0.9683(2) 0.0364(7) Uani 1 1 d . . . . .
H41A H 0.264779 1.093008 0.955053 0.044 Uiso 1 1 calc R U . . .
H41B H 0.233246 0.974774 0.906590 0.044 Uiso 1 1 calc R U . . .
C42 C 0.3595(3) 1.0257(4) 1.0214(3) 0.0522(10) Uani 1 1 d . . . . .
H42A H 0.381010 1.075971 1.083986 0.078 Uiso 1 1 calc R U . . .
H42B H 0.411149 1.040223 0.984800 0.078 Uiso 1 1 calc R U . . .
H42C H 0.352908 0.959390 1.029829 0.078 Uiso 1 1 calc R U . . .
C43 C 0.3521(3) 0.6641(3) 0.8224(3) 0.0447(8) Uani 1 1 d . . . . .
C44 C 0.2886(3) 0.7266(2) 0.6646(2) 0.0344(6) Uani 1 1 d . . . . .
H44 H 0.325537 0.713762 0.616845 0.041 Uiso 1 1 calc R U . . .
C45 C 0.1401(3) 0.8180(3) 0.6140(3) 0.0546(11) Uani 1 1 d D . . . .
C46A C 0.4057(5) 0.3413(6) 0.9339(7) 0.0437(18) Uani 0.756(12) 1 d . . P A 1
C46B C 0.4170(18) 0.3596(16) 0.897(2) 0.048(5) Uani 0.244(12) 1 d . . P A 2
C47 C 0.2009(3) 0.2532(2) 0.8314(2) 0.0364(7) Uani 1 1 d . . . . .
H47 H 0.159086 0.258571 0.875919 0.044 Uiso 1 1 calc R U . . .
C48 C 0.0855(4) 0.1547(4) 0.6456(4) 0.0739(15) Uani 1 1 d . . . . .
N1 N 0.52004(19) 0.05165(18) 0.64249(17) 0.0277(5) Uani 1 1 d . . . . .
N2 N 0.3304(2) 0.4279(2) 0.47427(18) 0.0328(5) Uani 1 1 d . . . . .
N3 N -0.03939(19) 0.46698(18) 0.85137(17) 0.0280(5) Uani 1 1 d . . . . .
N4 N 0.1796(2) 1.01330(19) 1.02433(17) 0.0297(5) Uani 1 1 d . . . . .
O1 O 0.46231(19) 0.8090(2) 0.7789(2) 0.0497(6) Uani 1 1 d . . . . .
O2 O 0.3086(2) 0.8292(2) 0.83869(18) 0.0502(6) Uani 1 1 d . . . . .
O3 O 0.1078(2) 0.6860(2) 0.70060(19) 0.0501(6) Uani 1 1 d . . . . .
O4 O 0.1266(3) 0.6343(3) 0.5352(2) 0.0703(10) Uani 1 1 d . . . . .
O5 O 0.3355(3) 0.3503(2) 0.7601(2) 0.0777(11) Uani 1 1 d . . . . .
O6 O 0.2785(2) 0.44108(18) 0.8956(2) 0.0459(6) Uani 1 1 d . . . . .
O7 O 0.2570(2) 0.1276(2) 0.7098(2) 0.0512(7) Uani 1 1 d . . . . .
O8 O 0.1085(3) 0.0680(2) 0.7752(2) 0.0601(8) Uani 1 1 d . . . . .
F1 F 0.4123(2) 0.6942(3) 0.9107(2) 0.0782(9) Uani 1 1 d . . . . .
F2 F 0.3874(3) 0.5998(2) 0.7688(2) 0.0742(8) Uani 1 1 d . . . . .
F3 F 0.25908(19) 0.6195(2) 0.8261(2) 0.0702(8) Uani 1 1 d . . . . .
F4A F 0.1979(7) 0.8659(10) 0.5673(10) 0.054(3) Uani 0.44(3) 1 d D . P B 1
F5A F 0.1690(13) 0.8832(8) 0.7043(7) 0.059(3) Uani 0.44(3) 1 d D . P B 1
F6A F 0.0390(8) 0.7923(18) 0.578(2) 0.070(6) Uani 0.44(3) 1 d D . P B 1
F7A F 0.4929(3) 0.4069(5) 0.9394(4) 0.0692(15) Uani 0.756(12) 1 d . . P A 1
F8A F 0.3854(4) 0.3613(3) 1.0199(4) 0.0602(12) Uani 0.756(12) 1 d . . P A 1
F9A F 0.4163(4) 0.2524(3) 0.9130(4) 0.081(2) Uani 0.756(12) 1 d . . P A 1
F4B F 0.1718(11) 0.8231(13) 0.5314(11) 0.081(3) Uani 0.56(3) 1 d D U P B 2
F5B F 0.1851(11) 0.8981(7) 0.6838(10) 0.089(4) Uani 0.56(3) 1 d D U P B 2
F6B F 0.0425(6) 0.8179(13) 0.5916(13) 0.051(2) Uani 0.56(3) 1 d D . P B 2
F7B F 0.4841(10) 0.4421(10) 0.9025(13) 0.059(4) Uani 0.244(12) 1 d . . P A 2
F8B F 0.4101(18) 0.3515(17) 0.982(2) 0.086(8) Uani 0.244(12) 1 d . U P A 2
F9B F 0.4437(10) 0.2823(11) 0.8497(15) 0.085(5) Uani 0.244(12) 1 d . U P A 2
F10 F 0.1323(4) 0.2240(4) 0.6096(2) 0.1106(14) Uani 1 1 d . . . . .
F11 F 0.0044(2) 0.1772(3) 0.6695(3) 0.1093(15) Uani 1 1 d . . . . .
F12 F 0.0508(4) 0.0682(3) 0.5783(3) 0.1284(18) Uani 1 1 d . . . . .
S1 S 0.63544(6) 0.15089(5) 0.55850(5) 0.03118(16) Uani 1 1 d . . . . .
S2 S 0.45768(6) 0.36139(6) 0.38964(5) 0.03357(17) Uani 1 1 d . . . . .
S3 S -0.13041(5) 0.56420(5) 0.95965(5) 0.02861(16) Uani 1 1 d . . . . .
S4 S 0.03950(6) 0.93068(5) 1.09835(5) 0.03174(17) Uani 1 1 d . . . . .
S5 S 0.35534(6) 0.77219(6) 0.77708(5) 0.03182(17) Uani 1 1 d . . . . .
S6 S 0.16174(6) 0.70172(6) 0.62931(5) 0.03400(17) Uani 1 1 d . . . . .
S7 S 0.29721(6) 0.35277(6) 0.84237(6) 0.03667(18) Uani 1 1 d . . . . .
S8 S 0.17275(6) 0.14472(6) 0.74787(5) 0.03452(18) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C2 1.393(5) . ?
C1 C6 1.394(4) . ?
C1 S1 1.743(3) . ?
C2 C3 1.395(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(4) . ?
C5 H5 0.9500 . ?
C6 N1 1.400(4) . ?
C7 N1 1.357(4) . ?
C7 C10 1.398(4) . ?
C7 S1 1.745(3) . ?
C8 N1 1.470(4) . ?
C8 C9 1.507(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.387(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(4) . ?
C12 H12 0.9500 . ?
C13 N2 1.361(4) . ?
C13 S2 1.743(3) . ?
C14 C19 1.389(5) . ?
C14 C15 1.393(5) . ?
C14 S2 1.746(3) . ?
C15 C16 1.384(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.398(5) . ?
C18 H18 0.9500 . ?
C19 N2 1.396(4) . ?
C20 N2 1.465(4) . ?
C20 C21 1.513(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C27 1.389(4) . ?
C22 C23 1.392(4) . ?
C22 S3 1.751(3) . ?
C23 C24 1.382(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.399(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.380(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.397(4) . ?
C26 H26 0.9500 . ?
C27 N3 1.395(4) . ?
C28 N3 1.361(4) . ?
C28 C31 1.394(4) . ?
C28 S3 1.742(3) . ?
C29 N3 1.463(4) . ?
C29 C30 1.515(5) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.387(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.392(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.397(4) . ?
C33 H33 0.9500 . ?
C34 N4 1.355(4) . ?
C34 S4 1.744(3) . ?
C35 C36 1.389(5) . ?
C35 C40 1.390(5) . ?
C35 S4 1.745(3) . ?
C36 C37 1.388(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.393(6) . ?
C37 H37 0.9500 . ?
C38 C39 1.398(5) . ?
C38 H38 0.9500 . ?
C39 C40 1.397(4) . ?
C39 H39 0.9500 . ?
C40 N4 1.399(4) . ?
C41 N4 1.465(4) . ?
C41 C42 1.517(5) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 F3 1.305(4) . ?
C43 F2 1.315(5) . ?
C43 F1 1.339(5) . ?
C43 S5 1.839(4) . ?
C44 S5 1.657(3) . ?
C44 S6 1.664(3) . ?
C44 H44 0.9500 . ?
C45 F5B 1.290(8) . ?
C45 F4A 1.321(7) . ?
C45 F6B 1.333(8) . ?
C45 F6A 1.333(9) . ?
C45 F5A 1.373(8) . ?
C45 F4B 1.384(8) . ?
C45 S6 1.835(4) . ?
C46A F9A 1.297(9) . ?
C46A F7A 1.315(9) . ?
C46A F8A 1.335(10) . ?
C46A S7 1.917(9) . ?
C46B F7B 1.29(3) . ?
C46B F8B 1.31(3) . ?
C46B F9B 1.34(3) . ?
C46B S7 1.68(2) . ?
C47 S7 1.658(3) . ?
C47 S8 1.661(3) . ?
C47 H47 0.9500 . ?
C48 F11 1.317(7) . ?
C48 F12 1.320(6) . ?
C48 F10 1.329(8) . ?
C48 S8 1.836(5) . ?
O1 S5 1.435(3) . ?
O2 S5 1.423(3) . ?
O3 S6 1.425(3) . ?
O4 S6 1.426(3) . ?
O5 S7 1.408(3) . ?
O6 S7 1.436(3) . ?
O7 S8 1.423(3) . ?
O8 S8 1.429(3) . ?

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
C2 C1 C6 120.9(3) . . ?
C2 C1 S1 128.6(2) . . ?
C6 C1 S1 110.5(2) . . ?
C1 C2 C3 118.0(3) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 122.0(3) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 117.4(3) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 121.3 . . ?
C1 C6 C5 121.1(3) . . ?
C1 C6 N1 112.6(2) . . ?
C5 C6 N1 126.3(3) . . ?
N1 C7 C10 125.7(3) . . ?
N1 C7 S1 110.9(2) . . ?
C10 C7 S1 123.4(2) . . ?
N1 C8 C9 112.1(3) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C7 122.6(3) . . ?
C11 C10 H10 118.7 . . ?
C7 C10 H10 118.7 . . ?
C12 C11 C10 124.7(3) . . ?
C12 C11 H11 117.7 . . ?
C10 C11 H11 117.7 . . ?
C11 C12 C13 123.0(3) . . ?
C11 C12 H12 118.5 . . ?
C13 C12 H12 118.5 . . ?
N2 C13 C12 125.9(3) . . ?
N2 C13 S2 110.7(2) . . ?
C12 C13 S2 123.5(2) . . ?
C19 C14 C15 121.0(3) . . ?
C19 C14 S2 110.5(2) . . ?
C15 C14 S2 128.5(3) . . ?
C16 C15 C14 117.9(4) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
C17 C16 C15 121.2(3) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 121.6(3) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C17 C18 C19 117.3(3) . . ?
C17 C18 H18 121.3 . . ?
C19 C18 H18 121.3 . . ?
C14 C19 N2 112.6(3) . . ?
C14 C19 C18 121.0(3) . . ?
N2 C19 C18 126.4(3) . . ?
N2 C20 C21 110.9(3) . . ?
N2 C20 H20A 109.5 . . ?
C21 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 108.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 121.8(3) . . ?
C27 C22 S3 110.5(2) . . ?
C23 C22 S3 127.7(3) . . ?
C24 C23 C22 117.8(3) . . ?
C24 C23 H23 121.1 . . ?
C22 C23 H23 121.1 . . ?
C23 C24 C25 120.7(3) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C26 C25 C24 121.4(3) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C25 C26 C27 118.2(3) . . ?
C25 C26 H26 120.9 . . ?
C27 C26 H26 120.9 . . ?
C22 C27 N3 112.7(3) . . ?
C22 C27 C26 120.1(3) . . ?
N3 C27 C26 127.2(3) . . ?
N3 C28 C31 125.3(3) . . ?
N3 C28 S3 111.0(2) . . ?
C31 C28 S3 123.8(2) . . ?
N3 C29 C30 111.4(3) . . ?
N3 C29 H29A 109.3 . . ?
C30 C29 H29A 109.3 . . ?
N3 C29 H29B 109.3 . . ?
C30 C29 H29B 109.3 . . ?
H29A C29 H29B 108.0 . . ?
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 . . ?
C32 C31 C28 121.9(3) . . ?
C32 C31 H31 119.0 . . ?
C28 C31 H31 119.0 . . ?
C31 C32 C33 125.7(3) . . ?
C31 C32 H32 117.2 . . ?
C33 C32 H32 117.2 . . ?
C32 C33 C34 121.3(3) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
N4 C34 C33 126.2(3) . . ?
N4 C34 S4 111.3(2) . . ?
C33 C34 S4 122.5(2) . . ?
C36 C35 C40 121.9(3) . . ?
C36 C35 S4 127.7(3) . . ?
C40 C35 S4 110.4(2) . . ?
C37 C36 C35 117.9(3) . . ?
C37 C36 H36 121.0 . . ?
C35 C36 H36 121.0 . . ?
C36 C37 C38 120.6(3) . . ?
C36 C37 H37 119.7 . . ?
C38 C37 H37 119.7 . . ?
C37 C38 C39 121.6(3) . . ?
C37 C38 H38 119.2 . . ?
C39 C38 H38 119.2 . . ?
C40 C39 C38 117.5(3) . . ?
C40 C39 H39 121.3 . . ?
C38 C39 H39 121.3 . . ?
C35 C40 C39 120.5(3) . . ?
C35 C40 N4 112.9(3) . . ?
C39 C40 N4 126.6(3) . . ?
N4 C41 C42 110.8(3) . . ?
N4 C41 H41A 109.5 . . ?
C42 C41 H41A 109.5 . . ?
N4 C41 H41B 109.5 . . ?
C42 C41 H41B 109.5 . . ?
H41A C41 H41B 108.1 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
F3 C43 F2 109.4(4) . . ?
F3 C43 F1 107.9(3) . . ?
F2 C43 F1 107.5(3) . . ?
F3 C43 S5 111.5(2) . . ?
F2 C43 S5 110.7(3) . . ?
F1 C43 S5 109.7(3) . . ?
S5 C44 S6 124.77(19) . . ?
S5 C44 H44 117.6 . . ?
S6 C44 H44 117.6 . . ?
F5B C45 F6B 105.0(10) . . ?
F4A C45 F6A 115.5(14) . . ?
F4A C45 F5A 103.2(7) . . ?
F6A C45 F5A 111.7(14) . . ?
F5B C45 F4B 112.4(7) . . ?
F6B C45 F4B 102.5(10) . . ?
F5B C45 S6 116.9(7) . . ?
F4A C45 S6 117.7(6) . . ?
F6B C45 S6 116.5(8) . . ?
F6A C45 S6 103.5(11) . . ?
F5A C45 S6 105.0(6) . . ?
F4B C45 S6 102.8(5) . . ?
F9A C46A F7A 109.5(6) . . ?
F9A C46A F8A 107.9(9) . . ?
F7A C46A F8A 107.6(6) . . ?
F9A C46A S7 112.1(5) . . ?
F7A C46A S7 109.9(7) . . ?
F8A C46A S7 109.7(5) . . ?
F7B C46B F8B 112(2) . . ?
F7B C46B F9B 109(2) . . ?
F8B C46B F9B 109(2) . . ?
F7B C46B S7 112.4(17) . . ?
F8B C46B S7 105(2) . . ?
F9B C46B S7 109.3(16) . . ?
S7 C47 S8 124.4(2) . . ?
S7 C47 H47 117.8 . . ?
S8 C47 H47 117.8 . . ?
F11 C48 F12 106.8(5) . . ?
F11 C48 F10 108.3(6) . . ?
F12 C48 F10 108.8(5) . . ?
F11 C48 S8 111.4(4) . . ?
F12 C48 S8 110.0(4) . . ?
F10 C48 S8 111.5(4) . . ?
C7 N1 C6 114.5(2) . . ?
C7 N1 C8 123.6(3) . . ?
C6 N1 C8 121.8(2) . . ?
C13 N2 C19 114.7(3) . . ?
C13 N2 C20 123.4(3) . . ?
C19 N2 C20 121.9(3) . . ?
C28 N3 C27 114.6(2) . . ?
C28 N3 C29 123.6(3) . . ?
C27 N3 C29 121.9(3) . . ?
C34 N4 C40 114.0(3) . . ?
C34 N4 C41 123.1(3) . . ?
C40 N4 C41 122.8(2) . . ?
C1 S1 C7 91.51(14) . . ?
C13 S2 C14 91.52(15) . . ?
C28 S3 C22 91.24(14) . . ?
C34 S4 C35 91.23(15) . . ?
O2 S5 O1 120.79(18) . . ?
O2 S5 C44 114.16(17) . . ?
O1 S5 C44 108.78(16) . . ?
O2 S5 C43 102.84(18) . . ?
O1 S5 C43 102.15(17) . . ?
C44 S5 C43 106.17(18) . . ?
O3 S6 O4 120.3(2) . . ?
O3 S6 C44 114.21(16) . . ?
O4 S6 C44 109.31(19) . . ?
O3 S6 C45 101.81(18) . . ?
O4 S6 C45 103.6(2) . . ?
C44 S6 C45 105.69(17) . . ?
O5 S7 O6 121.5(2) . . ?
O5 S7 C47 114.31(18) . . ?
O6 S7 C47 109.81(17) . . ?
O5 S7 C46B 85.7(11) . . ?
O6 S7 C46B 104.7(8) . . ?
C47 S7 C46B 119.0(9) . . ?
O5 S7 C46A 104.8(3) . . ?
O6 S7 C46A 100.8(2) . . ?
C47 S7 C46A 102.6(3) . . ?
O7 S8 O8 120.01(18) . . ?
O7 S8 C47 114.34(17) . . ?
O8 S8 C47 109.68(17) . . ?
O7 S8 C48 102.7(2) . . ?
O8 S8 C48 102.5(3) . . ?
C47 S8 C48 105.5(2) . . ?

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
C6 C1 C2 C3 -1.1(5) . . . . ?
S1 C1 C2 C3 177.9(3) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
S1 C1 C6 C5 -178.2(2) . . . . ?
C2 C1 C6 N1 -179.3(3) . . . . ?
S1 C1 C6 N1 1.5(3) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C4 C5 C6 N1 -179.6(3) . . . . ?
N1 C7 C10 C11 -169.4(3) . . . . ?
S1 C7 C10 C11 11.2(4) . . . . ?
C7 C10 C11 C12 -176.6(3) . . . . ?
C10 C11 C12 C13 -175.1(3) . . . . ?
C11 C12 C13 N2 -174.0(3) . . . . ?
C11 C12 C13 S2 6.3(4) . . . . ?
C19 C14 C15 C16 -1.3(5) . . . . ?
S2 C14 C15 C16 178.0(3) . . . . ?
C14 C15 C16 C17 0.7(5) . . . . ?
C15 C16 C17 C18 0.8(6) . . . . ?
C16 C17 C18 C19 -1.6(5) . . . . ?
C15 C14 C19 N2 -178.7(3) . . . . ?
S2 C14 C19 N2 1.9(3) . . . . ?
C15 C14 C19 C18 0.5(5) . . . . ?
S2 C14 C19 C18 -178.9(2) . . . . ?
C17 C18 C19 C14 1.0(5) . . . . ?
C17 C18 C19 N2 180.0(3) . . . . ?
C27 C22 C23 C24 -0.3(4) . . . . ?
S3 C22 C23 C24 178.4(2) . . . . ?
C22 C23 C24 C25 -0.2(5) . . . . ?
C23 C24 C25 C26 0.4(5) . . . . ?
C24 C25 C26 C27 -0.1(5) . . . . ?
C23 C22 C27 N3 179.9(3) . . . . ?
S3 C22 C27 N3 1.0(3) . . . . ?
C23 C22 C27 C26 0.6(4) . . . . ?
S3 C22 C27 C26 -178.3(2) . . . . ?
C25 C26 C27 C22 -0.4(4) . . . . ?
C25 C26 C27 N3 -179.6(3) . . . . ?
N3 C28 C31 C32 -173.3(3) . . . . ?
S3 C28 C31 C32 5.8(4) . . . . ?
C28 C31 C32 C33 -179.9(3) . . . . ?
C31 C32 C33 C34 -178.3(3) . . . . ?
C32 C33 C34 N4 -177.0(3) . . . . ?
C32 C33 C34 S4 3.5(4) . . . . ?
C40 C35 C36 C37 -0.8(4) . . . . ?
S4 C35 C36 C37 -180.0(2) . . . . ?
C35 C36 C37 C38 -0.1(5) . . . . ?
C36 C37 C38 C39 0.3(5) . . . . ?
C37 C38 C39 C40 0.4(5) . . . . ?
C36 C35 C40 C39 1.5(4) . . . . ?
S4 C35 C40 C39 -179.2(2) . . . . ?
C36 C35 C40 N4 -178.1(3) . . . . ?
S4 C35 C40 N4 1.2(3) . . . . ?
C38 C39 C40 C35 -1.3(5) . . . . ?
C38 C39 C40 N4 178.3(3) . . . . ?
C10 C7 N1 C6 -178.2(3) . . . . ?
S1 C7 N1 C6 1.2(3) . . . . ?
C10 C7 N1 C8 2.9(4) . . . . ?
S1 C7 N1 C8 -177.7(2) . . . . ?
C1 C6 N1 C7 -1.8(3) . . . . ?
C5 C6 N1 C7 177.9(3) . . . . ?
C1 C6 N1 C8 177.1(3) . . . . ?
C5 C6 N1 C8 -3.2(4) . . . . ?
C9 C8 N1 C7 -96.5(3) . . . . ?
C9 C8 N1 C6 84.6(3) . . . . ?
C12 C13 N2 C19 -178.7(3) . . . . ?
S2 C13 N2 C19 1.0(3) . . . . ?
C12 C13 N2 C20 -0.9(5) . . . . ?
S2 C13 N2 C20 178.8(2) . . . . ?
C14 C19 N2 C13 -1.9(4) . . . . ?
C18 C19 N2 C13 179.0(3) . . . . ?
C14 C19 N2 C20 -179.8(3) . . . . ?
C18 C19 N2 C20 1.1(5) . . . . ?
C21 C20 N2 C13 -97.2(4) . . . . ?
C21 C20 N2 C19 80.5(4) . . . . ?
C31 C28 N3 C27 179.7(3) . . . . ?
S3 C28 N3 C27 0.5(3) . . . . ?
C31 C28 N3 C29 0.6(4) . . . . ?
S3 C28 N3 C29 -178.5(2) . . . . ?
C22 C27 N3 C28 -1.0(3) . . . . ?
C26 C27 N3 C28 178.2(3) . . . . ?
C22 C27 N3 C29 178.0(3) . . . . ?
C26 C27 N3 C29 -2.7(4) . . . . ?
C30 C29 N3 C28 -92.1(4) . . . . ?
C30 C29 N3 C27 89.0(4) . . . . ?
C33 C34 N4 C40 180.0(3) . . . . ?
S4 C34 N4 C40 -0.5(3) . . . . ?
C33 C34 N4 C41 -2.5(4) . . . . ?
S4 C34 N4 C41 177.1(2) . . . . ?
C35 C40 N4 C34 -0.5(4) . . . . ?
C39 C40 N4 C34 179.9(3) . . . . ?
C35 C40 N4 C41 -178.0(3) . . . . ?
C39 C40 N4 C41 2.4(5) . . . . ?
C42 C41 N4 C34 -90.3(4) . . . . ?
C42 C41 N4 C40 87.0(4) . . . . ?
C2 C1 S1 C7 -179.8(3) . . . . ?
C6 C1 S1 C7 -0.7(2) . . . . ?
N1 C7 S1 C1 -0.3(2) . . . . ?
C10 C7 S1 C1 179.1(3) . . . . ?
N2 C13 S2 C14 0.1(2) . . . . ?
C12 C13 S2 C14 179.8(3) . . . . ?
C19 C14 S2 C13 -1.1(2) . . . . ?
C15 C14 S2 C13 179.5(3) . . . . ?
N3 C28 S3 C22 0.0(2) . . . . ?
C31 C28 S3 C22 -179.1(3) . . . . ?
C27 C22 S3 C28 -0.6(2) . . . . ?
C23 C22 S3 C28 -179.4(3) . . . . ?
N4 C34 S4 C35 1.0(2) . . . . ?
C33 C34 S4 C35 -179.4(2) . . . . ?
C36 C35 S4 C34 178.0(3) . . . . ?
C40 C35 S4 C34 -1.2(2) . . . . ?
S6 C44 S5 O2 -26.3(3) . . . . ?
S6 C44 S5 O1 -164.5(2) . . . . ?
S6 C44 S5 C43 86.2(3) . . . . ?
F3 C43 S5 O2 54.1(3) . . . . ?
F2 C43 S5 O2 176.2(3) . . . . ?
F1 C43 S5 O2 -65.3(3) . . . . ?
F3 C43 S5 O1 -180.0(3) . . . . ?
F2 C43 S5 O1 -58.0(3) . . . . ?
F1 C43 S5 O1 60.6(3) . . . . ?
F3 C43 S5 C44 -66.1(3) . . . . ?
F2 C43 S5 C44 56.0(3) . . . . ?
F1 C43 S5 C44 174.5(3) . . . . ?
S5 C44 S6 O3 -22.6(3) . . . . ?
S5 C44 S6 O4 -160.6(3) . . . . ?
S5 C44 S6 C45 88.4(3) . . . . ?
F5B C45 S6 O3 69.1(9) . . . . ?
F4A C45 S6 O3 165.8(7) . . . . ?
F6B C45 S6 O3 -56.1(10) . . . . ?
F6A C45 S6 O3 -65.4(15) . . . . ?
F5A C45 S6 O3 51.9(8) . . . . ?
F4B C45 S6 O3 -167.3(8) . . . . ?
F5B C45 S6 O4 -165.4(9) . . . . ?
F4A C45 S6 O4 -68.7(7) . . . . ?
F6B C45 S6 O4 69.3(10) . . . . ?
F6A C45 S6 O4 60.0(15) . . . . ?
F5A C45 S6 O4 177.3(8) . . . . ?
F4B C45 S6 O4 -41.9(8) . . . . ?
F5B C45 S6 C44 -50.5(9) . . . . ?
F4A C45 S6 C44 46.2(7) . . . . ?
F6B C45 S6 C44 -175.7(10) . . . . ?
F6A C45 S6 C44 175.0(15) . . . . ?
F5A C45 S6 C44 -67.7(8) . . . . ?
F4B C45 S6 C44 73.1(8) . . . . ?
S8 C47 S7 O5 18.2(4) . . . . ?
S8 C47 S7 O6 158.8(2) . . . . ?
S8 C47 S7 C46B -80.8(12) . . . . ?
S8 C47 S7 C46A -94.7(3) . . . . ?
F7B C46B S7 O5 66.0(19) . . . . ?
F8B C46B S7 O5 -172.6(17) . . . . ?
F9B C46B S7 O5 -55.8(18) . . . . ?
F7B C46B S7 O6 -55(2) . . . . ?
F8B C46B S7 O6 65.9(18) . . . . ?
F9B C46B S7 O6 -177.2(16) . . . . ?
F7B C46B S7 C47 -178.5(14) . . . . ?
F8B C46B S7 C47 -57.1(19) . . . . ?
F9B C46B S7 C47 60(2) . . . . ?
S7 C47 S8 O7 24.1(3) . . . . ?
S7 C47 S8 O8 162.2(3) . . . . ?
S7 C47 S8 C48 -88.0(3) . . . . ?
F11 C48 S8 O7 -176.0(4) . . . . ?
F12 C48 S8 O7 65.8(5) . . . . ?
F10 C48 S8 O7 -54.9(5) . . . . ?
F11 C48 S8 O8 58.8(4) . . . . ?
F12 C48 S8 O8 -59.3(5) . . . . ?
F10 C48 S8 O8 179.9(4) . . . . ?
F11 C48 S8 C47 -55.9(5) . . . . ?
F12 C48 S8 C47 -174.1(4) . . . . ?
F10 C48 S8 C47 65.1(5) . . . . ?

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 H2 F4A^a 0.95 2.36 3.121(8) 136.6 2_666 yes
C2 H2 F4B^b 0.95 2.39 3.175(8) 139.5 2_666 yes
C5 H5 O1 0.95 2.32 3.263(4) 171.2 1_545 yes
C8 H8B O7 0.99 2.53 3.301(4) 134.8 . yes
C9 H9C F9A^a 0.98 2.45 3.198(5) 133.2 . yes
C9 H9C F9B^b 0.98 2.28 3.208(14) 158.5 . yes
C10 H10 O7 0.95 2.51 3.450(4) 172.7 . yes
C12 H12 O5 0.95 2.65 3.455(4) 143.0 . yes
C15 H15 F2 0.95 2.37 3.217(5) 148.3 2_666 yes
C23 H23 O6 0.95 2.47 3.240(4) 138.5 2_567 yes
C29 H29B F3 0.99 2.46 3.408(4) 160.1 . yes
C31 H31 O3 0.95 2.60 3.346(4) 135.5 . yes
C31 H31 F3 0.95 2.60 3.464(4) 151.3 . yes
C33 H33 O2 0.95 2.49 3.430(4) 169.4 . yes
C36 H36 O8 0.95 2.58 3.316(5) 134.3 2_567 yes
C41 H41B O2 0.99 2.63 3.357(4) 130.4 . yes
C42 H42A O1 0.98 2.60 3.447(4) 144.8 2_677 yes
C2 H2 F4A^a 0.95 2.36 3.121(8) 136.6 2_666 yes
C2 H2 F4B^b 0.95 2.39 3.175(8) 139.5 2_666 yes
C5 H5 O1 0.95 2.32 3.263(4) 171.2 1_545 yes
C8 H8B O7 0.99 2.53 3.301(4) 134.8 . yes
C9 H9C F9A^a 0.98 2.45 3.198(5) 133.2 . yes
C9 H9C F9B^b 0.98 2.28 3.208(14) 158.5 . yes
C10 H10 O7 0.95 2.51 3.450(4) 172.7 . yes
C12 H12 O5 0.95 2.65 3.455(4) 143.0 . yes
C15 H15 F2 0.95 2.37 3.217(5) 148.3 2_666 yes
C23 H23 O6 0.95 2.47 3.240(4) 138.5 2_567 yes
C29 H29B F3 0.99 2.46 3.408(4) 160.1 . yes
C31 H31 O3 0.95 2.60 3.346(4) 135.5 . yes
C31 H31 F3 0.95 2.60 3.464(4) 151.3 . yes
C33 H33 O2 0.95 2.49 3.430(4) 169.4 . yes
C36 H36 O8 0.95 2.58 3.316(5) 134.3 2_567 yes
C41 H41B O2 0.99 2.63 3.357(4) 130.4 . yes
C42 H42A O1 0.98 2.60 3.447(4) 144.8 2_677 yes

_refine_diff_density_max         0.724
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.099

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Cy3_I
_database_code_depnum_ccdc_archive 'CCDC 1995228'
loop_
_audit_author_name
_audit_author_address
'David Pugh'
;Kings College London
United Kingdom
;
_audit_update_record             
;
2020-04-06 deposited with the CCDC.	2020-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N2 S2, I, C H2 Cl2'
_chemical_formula_sum            'C22 H23 Cl2 I N2 S2'
_chemical_formula_weight         577.34

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'
N N 0.0061 0.0033 '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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.9187(4)
_cell_length_b                   12.1261(7)
_cell_length_c                   13.0689(6)
_cell_angle_alpha                82.670(4)
_cell_angle_beta                 78.619(4)
_cell_angle_gamma                79.315(5)
_cell_volume                     1203.50(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    173.05(10)
_cell_measurement_reflns_used    3809
_cell_measurement_theta_min      2.5130
_cell_measurement_theta_max      29.9800

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    1.738
_shelx_estimated_absorpt_T_min   0.543
_shelx_estimated_absorpt_T_max   0.581
_exptl_absorpt_correction_T_min  0.84159
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.765
_oxdiff_exptl_absorpt_empirical_full_max 1.204
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      173.05(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            8396
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.919
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5456
_reflns_number_gt                4780
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'Olex-2, WinGX'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3, Mercury'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0299P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5456
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0785
_refine_ls_wR_factor_gt          0.0738
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.002

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
C1 C 0.0836(3) 0.6640(2) -0.0600(2) 0.0256(6) Uani 1 1 d . . . . .
C2 C -0.0258(3) 0.7681(2) -0.0520(3) 0.0307(6) Uani 1 1 d . . . . .
H2 H -0.061977 0.799578 0.013277 0.037 Uiso 1 1 calc R U . . .
C3 C -0.0798(4) 0.8239(3) -0.1417(3) 0.0366(7) Uani 1 1 d . . . . .
H3 H -0.154055 0.894954 -0.138157 0.044 Uiso 1 1 calc R U . . .
C4 C -0.0269(4) 0.7775(3) -0.2375(3) 0.0379(7) Uani 1 1 d . . . . .
H4 H -0.067387 0.816796 -0.298015 0.046 Uiso 1 1 calc R U . . .
C5 C 0.0837(4) 0.6749(3) -0.2457(2) 0.0337(7) Uani 1 1 d . . . . .
H5 H 0.120079 0.643562 -0.311126 0.040 Uiso 1 1 calc R U . . .
C6 C 0.1400(3) 0.6192(2) -0.1562(2) 0.0259(6) Uani 1 1 d . . . . .
C7 C 0.2801(3) 0.4802(2) -0.0491(2) 0.0234(5) Uani 1 1 d . . . . .
C8 C 0.3352(4) 0.4545(3) -0.2389(2) 0.0348(7) Uani 1 1 d . . . . .
H8A H 0.452966 0.415092 -0.229239 0.042 Uiso 1 1 calc R U . . .
H8B H 0.348797 0.508046 -0.302623 0.042 Uiso 1 1 calc R U . . .
C9 C 0.2274(5) 0.3689(3) -0.2543(3) 0.0512(9) Uani 1 1 d . . . . .
H9A H 0.219147 0.313152 -0.193015 0.077 Uiso 1 1 calc R U . . .
H9B H 0.283408 0.330850 -0.317107 0.077 Uiso 1 1 calc R U . . .
H9C H 0.110038 0.407355 -0.262749 0.077 Uiso 1 1 calc R U . . .
C10 C 0.3840(3) 0.3800(2) -0.0215(2) 0.0264(6) Uani 1 1 d . . . . .
H10 H 0.441527 0.333649 -0.075665 0.032 Uiso 1 1 calc R U . . .
C11 C 0.4095(3) 0.3430(2) 0.0797(2) 0.0265(6) Uani 1 1 d . . . . .
H11 H 0.350116 0.387734 0.134621 0.032 Uiso 1 1 calc R U . . .
C12 C 0.5174(3) 0.2439(2) 0.1045(2) 0.0278(6) Uani 1 1 d . . . . .
H12 H 0.573090 0.199066 0.049005 0.033 Uiso 1 1 calc R U . . .
C13 C 0.5745(4) 0.1735(3) 0.3938(2) 0.0342(7) Uani 1 1 d . . . . .
C14 C 0.5755(4) 0.1679(3) 0.5004(3) 0.0462(8) Uani 1 1 d . . . . .
H14 H 0.504513 0.224131 0.541523 0.055 Uiso 1 1 calc R U . . .
C15 C 0.6801(5) 0.0802(3) 0.5452(3) 0.0524(9) Uani 1 1 d . . . . .
H15 H 0.683023 0.076131 0.617936 0.063 Uiso 1 1 calc R U . . .
C16 C 0.7820(5) -0.0030(3) 0.4858(3) 0.0488(9) Uani 1 1 d . . . . .
H16 H 0.853604 -0.063167 0.518802 0.059 Uiso 1 1 calc R U . . .
C17 C 0.7819(4) -0.0005(3) 0.3800(3) 0.0391(7) Uani 1 1 d . . . . .
H17 H 0.851048 -0.058358 0.340055 0.047 Uiso 1 1 calc R U . . .
C18 C 0.6773(3) 0.0893(2) 0.3337(2) 0.0302(6) Uani 1 1 d . . . . .
C19 C 0.5510(3) 0.2047(2) 0.2043(2) 0.0258(6) Uani 1 1 d . . . . .
C20 C 0.7436(3) 0.0292(2) 0.1505(2) 0.0300(6) Uani 1 1 d . . . . .
H20A H 0.849914 -0.016592 0.172333 0.036 Uiso 1 1 calc R U . . .
H20B H 0.778724 0.070895 0.081617 0.036 Uiso 1 1 calc R U . . .
C21 C 0.6182(4) -0.0476(3) 0.1404(3) 0.0482(9) Uani 1 1 d . . . . .
H21A H 0.593331 -0.094650 0.206543 0.072 Uiso 1 1 calc R U . . .
H21B H 0.670895 -0.095858 0.083888 0.072 Uiso 1 1 calc R U . . .
H21C H 0.509260 -0.001890 0.124258 0.072 Uiso 1 1 calc R U . . .
C22 C 0.1289(6) 0.6162(4) 0.4136(3) 0.0858(15) Uani 1 1 d . . . . .
H22A H 0.089728 0.557323 0.382267 0.103 Uiso 1 1 calc R U . . .
H22B H 0.168523 0.672066 0.355944 0.103 Uiso 1 1 calc R U . . .
N1 N 0.2545(3) 0.51752(19) -0.14769(18) 0.0250(5) Uani 1 1 d . . . . .
N2 N 0.6603(3) 0.10996(19) 0.22852(18) 0.0262(5) Uani 1 1 d . . . . .
S1 S 0.17005(8) 0.57588(6) 0.03938(5) 0.02591(15) Uani 1 1 d . . . . .
S2 S 0.45808(9) 0.27467(7) 0.31602(6) 0.03595(18) Uani 1 1 d . . . . .
I1 I 0.19657(2) 0.82438(2) 0.17921(2) 0.03290(7) Uani 1 1 d . . . . .
Cl1 Cl 0.30381(13) 0.55461(10) 0.47499(9) 0.0676(3) Uani 1 1 d . . . . .
Cl2 Cl -0.04787(13) 0.68315(10) 0.49894(9) 0.0700(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C6 1.392(4) . ?
C1 C2 1.394(4) . ?
C1 S1 1.739(3) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C6 N1 1.394(3) . ?
C7 N1 1.352(3) . ?
C7 C10 1.385(4) . ?
C7 S1 1.735(3) . ?
C8 N1 1.471(3) . ?
C8 C9 1.514(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.383(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(4) . ?
C11 H11 0.9500 . ?
C12 C19 1.388(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(4) . ?
C13 C18 1.402(4) . ?
C13 S2 1.738(3) . ?
C14 C15 1.366(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(4) . ?
C17 H17 0.9500 . ?
C18 N2 1.395(4) . ?
C19 N2 1.348(3) . ?
C19 S2 1.747(3) . ?
C20 N2 1.478(3) . ?
C20 C21 1.515(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 Cl1 1.739(4) . ?
C22 Cl2 1.748(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?

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
C6 C1 C2 120.9(3) . . ?
C6 C1 S1 111.2(2) . . ?
C2 C1 S1 127.8(2) . . ?
C3 C2 C1 118.1(3) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 118.3(3) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C5 C6 C1 120.8(3) . . ?
C5 C6 N1 127.5(3) . . ?
C1 C6 N1 111.7(2) . . ?
N1 C7 C10 124.8(2) . . ?
N1 C7 S1 111.36(19) . . ?
C10 C7 S1 123.8(2) . . ?
N1 C8 C9 112.1(2) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C7 124.2(3) . . ?
C11 C10 H10 117.9 . . ?
C7 C10 H10 117.9 . . ?
C12 C11 C10 123.0(3) . . ?
C12 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
C11 C12 C19 125.2(3) . . ?
C11 C12 H12 117.4 . . ?
C19 C12 H12 117.4 . . ?
C14 C13 C18 120.3(3) . . ?
C14 C13 S2 129.1(3) . . ?
C18 C13 S2 110.6(2) . . ?
C15 C14 C13 119.0(3) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 120.8(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 121.6(3) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 117.9(3) . . ?
C16 C17 H17 121.1 . . ?
C18 C17 H17 121.1 . . ?
C17 C18 N2 127.5(3) . . ?
C17 C18 C13 120.5(3) . . ?
N2 C18 C13 112.0(3) . . ?
N2 C19 C12 125.4(2) . . ?
N2 C19 S2 110.7(2) . . ?
C12 C19 S2 123.9(2) . . ?
N2 C20 C21 110.3(2) . . ?
N2 C20 H20A 109.6 . . ?
C21 C20 H20A 109.6 . . ?
N2 C20 H20B 109.6 . . ?
C21 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Cl1 C22 Cl2 113.0(3) . . ?
Cl1 C22 H22A 109.0 . . ?
Cl2 C22 H22A 109.0 . . ?
Cl1 C22 H22B 109.0 . . ?
Cl2 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C7 N1 C6 114.7(2) . . ?
C7 N1 C8 123.1(2) . . ?
C6 N1 C8 122.2(2) . . ?
C19 N2 C18 115.3(2) . . ?
C19 N2 C20 121.9(2) . . ?
C18 N2 C20 122.6(2) . . ?
C7 S1 C1 90.91(13) . . ?
C13 S2 C19 91.47(14) . . ?

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
C6 C1 C2 C3 1.6(4) . . . . ?
S1 C1 C2 C3 -179.7(2) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C1 1.4(4) . . . . ?
C4 C5 C6 N1 -178.0(2) . . . . ?
C2 C1 C6 C5 -2.4(4) . . . . ?
S1 C1 C6 C5 178.7(2) . . . . ?
C2 C1 C6 N1 177.1(2) . . . . ?
S1 C1 C6 N1 -1.8(3) . . . . ?
N1 C7 C10 C11 179.8(2) . . . . ?
S1 C7 C10 C11 1.5(4) . . . . ?
C7 C10 C11 C12 -178.3(2) . . . . ?
C10 C11 C12 C19 178.2(2) . . . . ?
C18 C13 C14 C15 1.1(4) . . . . ?
S2 C13 C14 C15 -179.2(2) . . . . ?
C13 C14 C15 C16 -0.9(5) . . . . ?
C14 C15 C16 C17 0.0(5) . . . . ?
C15 C16 C17 C18 0.8(5) . . . . ?
C16 C17 C18 N2 178.4(3) . . . . ?
C16 C17 C18 C13 -0.6(4) . . . . ?
C14 C13 C18 C17 -0.3(4) . . . . ?
S2 C13 C18 C17 180.0(2) . . . . ?
C14 C13 C18 N2 -179.5(2) . . . . ?
S2 C13 C18 N2 0.8(3) . . . . ?
C11 C12 C19 N2 -177.8(2) . . . . ?
C11 C12 C19 S2 1.0(4) . . . . ?
C10 C7 N1 C6 178.1(2) . . . . ?
S1 C7 N1 C6 -3.5(3) . . . . ?
C10 C7 N1 C8 0.3(4) . . . . ?
S1 C7 N1 C8 178.75(18) . . . . ?
C5 C6 N1 C7 -177.1(2) . . . . ?
C1 C6 N1 C7 3.4(3) . . . . ?
C5 C6 N1 C8 0.7(4) . . . . ?
C1 C6 N1 C8 -178.8(2) . . . . ?
C9 C8 N1 C7 86.2(3) . . . . ?
C9 C8 N1 C6 -91.5(3) . . . . ?
C12 C19 N2 C18 178.1(2) . . . . ?
S2 C19 N2 C18 -0.8(3) . . . . ?
C12 C19 N2 C20 -7.0(4) . . . . ?
S2 C19 N2 C20 174.09(17) . . . . ?
C17 C18 N2 C19 -179.1(3) . . . . ?
C13 C18 N2 C19 0.0(3) . . . . ?
C17 C18 N2 C20 6.0(4) . . . . ?
C13 C18 N2 C20 -174.8(2) . . . . ?
C21 C20 N2 C19 -81.3(3) . . . . ?
C21 C20 N2 C18 93.3(3) . . . . ?
N1 C7 S1 C1 1.99(18) . . . . ?
C10 C7 S1 C1 -179.5(2) . . . . ?
C6 C1 S1 C7 -0.09(19) . . . . ?
C2 C1 S1 C7 -178.9(2) . . . . ?
C14 C13 S2 C19 179.2(3) . . . . ?
C18 C13 S2 C19 -1.0(2) . . . . ?
N2 C19 S2 C13 1.04(19) . . . . ?
C12 C19 S2 C13 -177.9(2) . . . . ?

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
C5 H5 Cl2 0.95 2.99 3.671(3) 130.1 1_554 yes
C8 H8B Cl1 0.99 2.97 3.823(3) 145.2 1_554 yes
C10 H10 I1 0.95 3.29 4.119(3) 147.2 2_665 yes
C12 H12 I1 0.95 3.19 4.042(3) 150.1 2_665 yes
C17 H17 I1 0.95 3.31 4.197(3) 155.6 1_645 yes
C20 H20A I1 0.99 3.06 4.021(3) 164.5 1_645 yes
C22 H22B I1 0.99 2.77 3.731(5) 164.7 . yes

_refine_diff_density_max         0.579
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.085

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Cy3_BF4_I
_database_code_depnum_ccdc_archive 'CCDC 1995229'
loop_
_audit_author_name
_audit_author_address
'David Pugh'
;Kings College London
United Kingdom
;
_audit_update_record             
;
2020-04-06 deposited with the CCDC.	2020-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N2 S2, 0.43(B F4), I0.57'
_chemical_formula_sum            'C21 H21 B0.43 F1.72 I0.57 N2 S2'
_chemical_formula_weight         475.22

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'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.7575(9)
_cell_length_b                   19.0198(8)
_cell_length_c                   15.2682(7)
_cell_angle_alpha                90
_cell_angle_beta                 114.649(6)
_cell_angle_gamma                90
_cell_volume                     4686.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173.00(14)
_cell_measurement_reflns_used    3153
_cell_measurement_theta_min      2.5350
_cell_measurement_theta_max      28.1380

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             1927
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.001
_shelx_estimated_absorpt_T_min   0.788
_shelx_estimated_absorpt_T_max   0.825
_exptl_absorpt_correction_T_min  0.89571
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.920
_oxdiff_exptl_absorpt_empirical_full_max 1.056
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      173.00(14)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            9207
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.524
_diffrn_reflns_theta_max         29.374
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5366
_reflns_number_gt                3830
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The anion is a mixture of BF4 and I, resulting from an incomplete salt
metathesis of the starting material (Cy3 iodide). Both anions occupied the
same site within the unit cell, which was modelled using standard PART 
instructions and the occupancy was left free to refine. This approach 
necessitated the use of DFIX and ISOR restraints to keep the BF4 anion in 
a sensible geometry with sensible ellipsoids.

There was also some highly disordered and partially occupied solvent 
molecules within the unit cell. One molecule of CH2Cl2 and one molecule of 
methanol were identified but could not be satisfactorily modelled, hence
these were removed using SQUEEZE.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0325P)²+0.8974P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5366
_refine_ls_number_parameters     283
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0832
_refine_ls_wR_factor_gt          0.0743
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002

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
C1 C 0.43708(12) 0.75287(12) 0.93756(16) 0.0457(6) Uani 1 1 d . . . . .
C2 C 0.45533(15) 0.79802(15) 1.0157(2) 0.0641(8) Uani 1 1 d . . . . .
H2 H 0.462729 0.846997 1.009918 0.077 Uiso 1 1 calc R U . . .
C3 C 0.46230(16) 0.7691(2) 1.1018(2) 0.0773(10) Uani 1 1 d . . . . .
H3 H 0.475371 0.798541 1.156492 0.093 Uiso 1 1 calc R U . . .
C4 C 0.45064(15) 0.69876(19) 1.10933(19) 0.0688(8) Uani 1 1 d . . . . .
H4 H 0.455298 0.680501 1.169294 0.083 Uiso 1 1 calc R U . . .
C5 C 0.43234(12) 0.65338(14) 1.03272(16) 0.0498(6) Uani 1 1 d . . . . .
H5 H 0.424232 0.604579 1.038919 0.060 Uiso 1 1 calc R U . . .
C6 C 0.42621(11) 0.68168(12) 0.94629(15) 0.0385(5) Uani 1 1 d . . . . .
C7 C 0.40248(11) 0.68643(11) 0.78530(15) 0.0364(5) Uani 1 1 d . . . . .
C8 C 0.38350(12) 0.66249(12) 0.69258(14) 0.0391(5) Uani 1 1 d . . . . .
H8 H 0.376092 0.613346 0.681066 0.047 Uiso 1 1 calc R U . . .
C9 C 0.37466(11) 0.70558(12) 0.61578(15) 0.0416(5) Uani 1 1 d . . . . .
H9 H 0.382892 0.754702 0.626902 0.050 Uiso 1 1 calc R U . . .
C10 C 0.35444(12) 0.68054(13) 0.52370(15) 0.0444(5) Uani 1 1 d . . . . .
H10 H 0.349311 0.631132 0.513822 0.053 Uiso 1 1 calc R U . . .
C11 C 0.34111(12) 0.72329(12) 0.44450(15) 0.0416(5) Uani 1 1 d . . . . .
C12 C 0.32028(12) 0.81887(13) 0.32584(15) 0.0425(5) Uani 1 1 d . . . . .
C13 C 0.31179(13) 0.87865(14) 0.27084(17) 0.0522(6) Uani 1 1 d . . . . .
H13 H 0.317875 0.924265 0.298319 0.063 Uiso 1 1 calc R U . . .
C14 C 0.29405(14) 0.86948(16) 0.17407(18) 0.0584(7) Uani 1 1 d . . . . .
H14 H 0.288202 0.909511 0.134542 0.070 Uiso 1 1 calc R U . . .
C15 C 0.28479(14) 0.80337(16) 0.13445(17) 0.0570(7) Uani 1 1 d . . . . .
H15 H 0.271942 0.798923 0.067746 0.068 Uiso 1 1 calc R U . . .
C16 C 0.29361(13) 0.74303(14) 0.18872(16) 0.0507(6) Uani 1 1 d . . . . .
H16 H 0.287014 0.697572 0.160696 0.061 Uiso 1 1 calc R U . . .
C17 C 0.31259(12) 0.75202(13) 0.28623(15) 0.0436(5) Uani 1 1 d . . . . .
C18 C 0.39630(12) 0.56890(11) 0.85247(14) 0.0383(5) Uani 1 1 d . . . . .
H18A H 0.355512 0.556363 0.786838 0.046 Uiso 1 1 calc R U . . .
H18B H 0.374422 0.552517 0.898890 0.046 Uiso 1 1 calc R U . . .
C19 C 0.47756(13) 0.53233(11) 0.87307(16) 0.0440(5) Uani 1 1 d . . . . .
H19A H 0.500659 0.550184 0.829238 0.066 Uiso 1 1 calc R U . . .
H19B H 0.468147 0.481584 0.863490 0.066 Uiso 1 1 calc R U . . .
H19C H 0.516554 0.541509 0.939841 0.066 Uiso 1 1 calc R U . . .
C20 C 0.32494(15) 0.62425(13) 0.33248(17) 0.0548(6) Uani 1 1 d . . . . .
H20A H 0.367205 0.599768 0.388729 0.066 Uiso 1 1 calc R U . . .
H20B H 0.340360 0.618622 0.277594 0.066 Uiso 1 1 calc R U . . .
C21 C 0.24166(16) 0.59030(14) 0.3074(2) 0.0698(8) Uani 1 1 d . . . . .
H21A H 0.225414 0.596693 0.360870 0.105 Uiso 1 1 calc R U . . .
H21B H 0.245256 0.539962 0.295983 0.105 Uiso 1 1 calc R U . . .
H21C H 0.200237 0.612191 0.249133 0.105 Uiso 1 1 calc R U . . .
N1 N 0.40662(9) 0.64561(9) 0.85980(11) 0.0346(4) Uani 1 1 d . . . . .
N2 N 0.32533(10) 0.69923(10) 0.35491(12) 0.0434(4) Uani 1 1 d . . . . .
S1 S 0.42442(3) 0.77357(3) 0.82086(5) 0.04884(17) Uani 1 1 d . . . . .
S2 S 0.34026(3) 0.81453(3) 0.44758(4) 0.04586(17) Uani 1 1 d . . . . .
B1 B 0.7080(5) 0.5267(5) 0.4197(6) 0.069(7) Uani 0.4296(10) 1 d D U P A 1
F1 F 0.7548(2) 0.58762(19) 0.4438(3) 0.0816(12) Uani 0.4296(10) 1 d D . P A 1
F2 F 0.6392(3) 0.5382(2) 0.3383(3) 0.0912(13) Uani 0.4296(10) 1 d D . P A 1
F3 F 0.7545(3) 0.4749(2) 0.3988(3) 0.1000(15) Uani 0.4296(10) 1 d D . P A 1
F4 F 0.6887(2) 0.50488(18) 0.4924(2) 0.0682(10) Uani 0.4296(10) 1 d D . P A 1
I1 I 0.71844(4) 0.52048(3) 0.42076(3) 0.0553(2) Uani 0.5704(10) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C6 1.382(3) . ?
C1 C2 1.394(3) . ?
C1 S1 1.745(2) . ?
C2 C3 1.383(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.366(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 N1 1.397(2) . ?
C7 N1 1.354(2) . ?
C7 C8 1.388(3) . ?
C7 S1 1.737(2) . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(3) . ?
C10 H10 0.9500 . ?
C11 N2 1.356(3) . ?
C11 S2 1.736(2) . ?
C12 C13 1.384(3) . ?
C12 C17 1.390(3) . ?
C12 S2 1.743(2) . ?
C13 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.375(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.393(3) . ?
C16 H16 0.9500 . ?
C17 N2 1.400(3) . ?
C18 N1 1.469(2) . ?
C18 C19 1.512(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 N2 1.466(3) . ?
C20 C21 1.509(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
B1 F2 1.349(8) . ?
B1 F4 1.356(8) . ?
B1 F1 1.384(8) . ?
B1 F3 1.405(9) . ?

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
C6 C1 C2 120.9(2) . . ?
C6 C1 S1 110.84(16) . . ?
C2 C1 S1 128.3(2) . . ?
C3 C2 C1 117.8(3) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 122.2(3) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C4 C5 C6 117.5(3) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 121.3 . . ?
C1 C6 C5 120.9(2) . . ?
C1 C6 N1 112.31(19) . . ?
C5 C6 N1 126.8(2) . . ?
N1 C7 C8 125.02(19) . . ?
N1 C7 S1 110.98(15) . . ?
C8 C7 S1 124.00(16) . . ?
C9 C8 C7 124.3(2) . . ?
C9 C8 H8 117.9 . . ?
C7 C8 H8 117.9 . . ?
C10 C9 C8 123.2(2) . . ?
C10 C9 H9 118.4 . . ?
C8 C9 H9 118.4 . . ?
C9 C10 C11 124.0(2) . . ?
C9 C10 H10 118.0 . . ?
C11 C10 H10 118.0 . . ?
N2 C11 C10 124.6(2) . . ?
N2 C11 S2 111.35(15) . . ?
C10 C11 S2 124.06(18) . . ?
C13 C12 C17 121.4(2) . . ?
C13 C12 S2 127.5(2) . . ?
C17 C12 S2 111.11(16) . . ?
C12 C13 C14 117.5(2) . . ?
C12 C13 H13 121.2 . . ?
C14 C13 H13 121.2 . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 122.1(2) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C15 C16 C17 117.0(2) . . ?
C15 C16 H16 121.5 . . ?
C17 C16 H16 121.5 . . ?
C12 C17 C16 120.9(2) . . ?
C12 C17 N2 111.97(19) . . ?
C16 C17 N2 127.1(2) . . ?
N1 C18 C19 111.29(16) . . ?
N1 C18 H18A 109.4 . . ?
C19 C18 H18A 109.4 . . ?
N1 C18 H18B 109.4 . . ?
C19 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C21 112.59(18) . . ?
N2 C20 H20A 109.1 . . ?
C21 C20 H20A 109.1 . . ?
N2 C20 H20B 109.1 . . ?
C21 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C7 N1 C6 114.68(18) . . ?
C7 N1 C18 122.97(17) . . ?
C6 N1 C18 122.26(17) . . ?
C11 N2 C17 114.47(19) . . ?
C11 N2 C20 122.87(18) . . ?
C17 N2 C20 122.62(19) . . ?
C7 S1 C1 91.17(10) . . ?
C11 S2 C12 91.07(11) . . ?
F2 B1 F4 111.3(6) . . ?
F2 B1 F1 108.8(7) . . ?
F4 B1 F1 111.5(7) . . ?
F2 B1 F3 107.3(7) . . ?
F4 B1 F3 110.2(7) . . ?
F1 B1 F3 107.6(6) . . ?

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
C6 C1 C2 C3 0.1(3) . . . . ?
S1 C1 C2 C3 179.91(18) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
S1 C1 C6 C5 -179.15(15) . . . . ?
C2 C1 C6 N1 178.70(19) . . . . ?
S1 C1 C6 N1 -1.1(2) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C4 C5 C6 N1 -178.54(19) . . . . ?
N1 C7 C8 C9 175.95(18) . . . . ?
S1 C7 C8 C9 -4.2(3) . . . . ?
C7 C8 C9 C10 -178.95(19) . . . . ?
C8 C9 C10 C11 176.58(19) . . . . ?
C9 C10 C11 N2 176.54(19) . . . . ?
C9 C10 C11 S2 -5.0(3) . . . . ?
C17 C12 C13 C14 0.9(3) . . . . ?
S2 C12 C13 C14 -178.60(17) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C13 C12 C17 C16 -1.9(3) . . . . ?
S2 C12 C17 C16 177.72(15) . . . . ?
C13 C12 C17 N2 178.62(18) . . . . ?
S2 C12 C17 N2 -1.8(2) . . . . ?
C15 C16 C17 C12 1.4(3) . . . . ?
C15 C16 C17 N2 -179.16(19) . . . . ?
C8 C7 N1 C6 -179.50(18) . . . . ?
S1 C7 N1 C6 0.6(2) . . . . ?
C8 C7 N1 C18 4.0(3) . . . . ?
S1 C7 N1 C18 -175.89(13) . . . . ?
C1 C6 N1 C7 0.3(2) . . . . ?
C5 C6 N1 C7 178.21(19) . . . . ?
C1 C6 N1 C18 176.87(16) . . . . ?
C5 C6 N1 C18 -5.2(3) . . . . ?
C19 C18 N1 C7 86.6(2) . . . . ?
C19 C18 N1 C6 -89.7(2) . . . . ?
C10 C11 N2 C17 178.96(18) . . . . ?
S2 C11 N2 C17 0.4(2) . . . . ?
C10 C11 N2 C20 -3.4(3) . . . . ?
S2 C11 N2 C20 177.99(15) . . . . ?
C12 C17 N2 C11 0.9(2) . . . . ?
C16 C17 N2 C11 -178.52(19) . . . . ?
C12 C17 N2 C20 -176.70(18) . . . . ?
C16 C17 N2 C20 3.8(3) . . . . ?
C21 C20 N2 C11 87.0(2) . . . . ?
C21 C20 N2 C17 -95.5(2) . . . . ?
N1 C7 S1 C1 -1.06(15) . . . . ?
C8 C7 S1 C1 179.07(18) . . . . ?
C6 C1 S1 C7 1.24(15) . . . . ?
C2 C1 S1 C7 -178.6(2) . . . . ?
N2 C11 S2 C12 -1.15(15) . . . . ?
C10 C11 S2 C12 -179.77(18) . . . . ?
C13 C12 S2 C11 -178.75(19) . . . . ?
C17 C12 S2 C11 1.67(15) . . . . ?

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
C5 H5 I1_$1 0.95 3.26 3.956(3) 131.2 2_656
C8 H8 I1_$2 0.95 3.09 3.971(2) 155.3 5_666
C13 H13 F3_$3 0.95 2.45 3.140(5) 129.7 3_455
C16 H16 F1_$4 0.95 2.55 3.481(5) 168.2 2_655
C18 H18B F4_$1 0.99 2.53 3.515(4) 175.7 2_656
C20 H20B F2_$4 0.99 2.48 3.357(4) 147.8 2_655
C21 H21C S1_$5 0.98 2.96 3.797(3) 143.5 7_566

_refine_diff_density_max         0.426
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.048



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# Please retain this information to preserve the provenance of 
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data_Cy3_OTf
_database_code_depnum_ccdc_archive 'CCDC 1995225'
loop_
_audit_author_name
_audit_author_address
'David Pugh'
;Kings College London
United Kingdom
;
_audit_update_record             
;
2020-04-06 deposited with the CCDC.	2020-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N2 S2, C F3 O3 S'
_chemical_formula_sum            'C22 H21 F3 N2 O3 S3'
_chemical_formula_weight         514.59

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.3057(4)
_cell_length_b                   12.0660(4)
_cell_length_c                   14.7108(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.185(4)
_cell_angle_gamma                90
_cell_volume                     2243.81(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173.00(14)
_cell_measurement_reflns_used    3136
_cell_measurement_theta_min      3.3030
_cell_measurement_theta_max      27.9360

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.384
_shelx_estimated_absorpt_T_min   0.894
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_T_min  0.94199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.966
_oxdiff_exptl_absorpt_empirical_full_max 1.038
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      173.00(14)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            7912
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.471
_diffrn_reflns_theta_max         28.277
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.819
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4549
_reflns_number_gt                3648
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'Olex-2, WinGX'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-III, Mercury'
_computing_publication_material  'enCIFer, WinGX'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²+1.0329P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4549
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0845
_refine_ls_wR_factor_gt          0.0772
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002

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
C1 C 0.02620(15) 0.95342(16) 0.37594(13) 0.0208(4) Uani 1 1 d . . . . .
C2 C -0.05831(15) 0.88434(16) 0.37392(13) 0.0200(4) Uani 1 1 d . . . . .
C3 C -0.15474(15) 0.92809(16) 0.37373(14) 0.0234(4) Uani 1 1 d . . . . .
H3 H -0.212312 0.881209 0.373108 0.028 Uiso 1 1 calc R U . . .
C4 C -0.16442(16) 1.04230(17) 0.37448(14) 0.0270(5) Uani 1 1 d . . . . .
H4 H -0.229952 1.074150 0.373778 0.032 Uiso 1 1 calc R U . . .
C5 C -0.08019(17) 1.11128(17) 0.37624(15) 0.0292(5) Uani 1 1 d . . . . .
H5 H -0.089117 1.189370 0.376807 0.035 Uiso 1 1 calc R U . . .
C6 C 0.01629(16) 1.06818(17) 0.37718(14) 0.0254(5) Uani 1 1 d . . . . .
H6 H 0.073959 1.115309 0.378622 0.031 Uiso 1 1 calc R U . . .
C7 C 0.06816(14) 0.75162(16) 0.37330(13) 0.0202(4) Uani 1 1 d . . . . .
C8 C 0.11043(15) 0.64645(16) 0.37412(14) 0.0220(4) Uani 1 1 d . . . . .
H8 H 0.065586 0.584904 0.373168 0.026 Uiso 1 1 calc R U . . .
C9 C 0.21384(15) 0.62459(16) 0.37626(13) 0.0211(4) Uani 1 1 d . . . . .
H9 H 0.258803 0.685419 0.375230 0.025 Uiso 1 1 calc R U . . .
C10 C 0.25404(15) 0.51908(16) 0.37978(14) 0.0215(4) Uani 1 1 d . . . . .
H10 H 0.209352 0.458675 0.382690 0.026 Uiso 1 1 calc R U . . .
C11 C 0.35687(15) 0.49542(16) 0.37932(13) 0.0195(4) Uani 1 1 d . . . . .
C12 C 0.53877(14) 0.49229(15) 0.36666(13) 0.0184(4) Uani 1 1 d . . . . .
C13 C 0.63806(15) 0.50559(17) 0.35529(14) 0.0230(4) Uani 1 1 d . . . . .
H13 H 0.660922 0.575860 0.340245 0.028 Uiso 1 1 calc R U . . .
C14 C 0.70238(16) 0.41329(17) 0.36659(14) 0.0259(5) Uani 1 1 d . . . . .
H14 H 0.770329 0.419886 0.358720 0.031 Uiso 1 1 calc R U . . .
C15 C 0.66866(16) 0.31092(18) 0.38934(15) 0.0289(5) Uani 1 1 d . . . . .
H15 H 0.714094 0.248582 0.396550 0.035 Uiso 1 1 calc R U . . .
C16 C 0.57023(16) 0.29769(17) 0.40177(15) 0.0276(5) Uani 1 1 d . . . . .
H16 H 0.548043 0.227661 0.418028 0.033 Uiso 1 1 calc R U . . .
C17 C 0.50528(15) 0.38992(16) 0.38971(14) 0.0210(4) Uani 1 1 d . . . . .
C18 C -0.10880(15) 0.68382(16) 0.37107(15) 0.0233(4) Uani 1 1 d . . . . .
H18A H -0.097134 0.620382 0.332870 0.028 Uiso 1 1 calc R U . . .
H18B H -0.181690 0.711365 0.340762 0.028 Uiso 1 1 calc R U . . .
C19 C -0.09695(18) 0.64529(19) 0.47195(16) 0.0354(5) Uani 1 1 d . . . . .
H19A H -0.146920 0.584915 0.469738 0.053 Uiso 1 1 calc R U . . .
H19B H -0.111703 0.707189 0.509011 0.053 Uiso 1 1 calc R U . . .
H19C H -0.024561 0.618864 0.502323 0.053 Uiso 1 1 calc R U . . .
C20 C 0.35562(17) 0.29887(17) 0.43232(16) 0.0288(5) Uani 1 1 d . . . . .
H20A H 0.306045 0.325786 0.465515 0.035 Uiso 1 1 calc R U . . .
H20B H 0.411912 0.255726 0.478818 0.035 Uiso 1 1 calc R U . . .
C21 C 0.29755(18) 0.2254(2) 0.35112(19) 0.0419(6) Uani 1 1 d . . . . .
H21A H 0.237472 0.265807 0.308233 0.063 Uiso 1 1 calc R U . . .
H21B H 0.271736 0.159720 0.376181 0.063 Uiso 1 1 calc R U . . .
H21C H 0.345385 0.202378 0.315700 0.063 Uiso 1 1 calc R U . . .
C22 C 0.4921(2) 0.06377(19) 0.63312(17) 0.0396(6) Uani 1 1 d . . . . .
N1 N -0.03313(12) 0.77215(13) 0.37093(11) 0.0191(4) Uani 1 1 d . . . . .
N2 N 0.40346(12) 0.39481(13) 0.39867(12) 0.0216(4) Uani 1 1 d . . . . .
O1 O 0.38824(11) 0.22518(12) 0.67105(11) 0.0332(4) Uani 1 1 d . . . . .
O2 O 0.55675(11) 0.17771(13) 0.78726(11) 0.0383(4) Uani 1 1 d . . . . .
O3 O 0.40592(12) 0.05814(13) 0.76622(12) 0.0430(4) Uani 1 1 d . . . . .
F1 F 0.40629(15) 0.02963(15) 0.56463(12) 0.0797(6) Uani 1 1 d . . . . .
F2 F 0.54974(14) -0.02506(12) 0.66757(11) 0.0637(5) Uani 1 1 d . . . . .
F3 F 0.54737(14) 0.12578(14) 0.59125(12) 0.0664(5) Uani 1 1 d . . . . .
S1 S 0.13670(4) 0.87545(4) 0.37554(4) 0.02479(13) Uani 1 1 d . . . . .
S2 S 0.43967(4) 0.59169(4) 0.35171(4) 0.02187(13) Uani 1 1 d . . . . .
S3 S 0.45677(4) 0.13984(4) 0.72519(4) 0.02378(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C6 1.392(3) . ?
C1 C2 1.393(3) . ?
C1 S1 1.7471(19) . ?
C2 C3 1.387(3) . ?
C2 N1 1.398(2) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.360(2) . ?
C7 C8 1.387(3) . ?
C7 S1 1.745(2) . ?
C8 C9 1.392(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.376(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.400(3) . ?
C10 H10 0.9500 . ?
C11 N2 1.352(2) . ?
C11 S2 1.7342(19) . ?
C12 C17 1.390(3) . ?
C12 C13 1.392(3) . ?
C12 S2 1.7449(19) . ?
C13 C14 1.383(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 N2 1.403(2) . ?
C18 N1 1.467(2) . ?
C18 C19 1.516(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 N2 1.479(3) . ?
C20 C21 1.495(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 F2 1.323(3) . ?
C22 F3 1.328(3) . ?
C22 F1 1.331(3) . ?
C22 S3 1.815(2) . ?
O1 S3 1.4397(15) . ?
O2 S3 1.4333(15) . ?
O3 S3 1.4313(16) . ?

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
C6 C1 C2 121.11(18) . . ?
C6 C1 S1 128.26(16) . . ?
C2 C1 S1 110.64(14) . . ?
C3 C2 C1 120.84(18) . . ?
C3 C2 N1 126.80(18) . . ?
C1 C2 N1 112.35(16) . . ?
C4 C3 C2 117.86(19) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 C5 121.32(19) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 121.08(19) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 117.79(19) . . ?
C5 C6 H6 121.1 . . ?
C1 C6 H6 121.1 . . ?
N1 C7 C8 124.26(18) . . ?
N1 C7 S1 110.63(14) . . ?
C8 C7 S1 125.11(15) . . ?
C7 C8 C9 124.69(19) . . ?
C7 C8 H8 117.7 . . ?
C9 C8 H8 117.7 . . ?
C10 C9 C8 123.12(19) . . ?
C10 C9 H9 118.4 . . ?
C8 C9 H9 118.4 . . ?
C9 C10 C11 123.90(18) . . ?
C9 C10 H10 118.0 . . ?
C11 C10 H10 118.0 . . ?
N2 C11 C10 124.51(18) . . ?
N2 C11 S2 111.57(14) . . ?
C10 C11 S2 123.91(15) . . ?
C17 C12 C13 121.34(18) . . ?
C17 C12 S2 110.75(14) . . ?
C13 C12 S2 127.88(15) . . ?
C14 C13 C12 117.90(19) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
C13 C14 C15 120.69(19) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 121.53(19) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C17 C16 C15 117.87(19) . . ?
C17 C16 H16 121.1 . . ?
C15 C16 H16 121.1 . . ?
C16 C17 C12 120.66(18) . . ?
C16 C17 N2 127.13(18) . . ?
C12 C17 N2 112.21(16) . . ?
N1 C18 C19 111.26(16) . . ?
N1 C18 H18A 109.4 . . ?
C19 C18 H18A 109.4 . . ?
N1 C18 H18B 109.4 . . ?
C19 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C21 111.47(19) . . ?
N2 C20 H20A 109.3 . . ?
C21 C20 H20A 109.3 . . ?
N2 C20 H20B 109.3 . . ?
C21 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
F2 C22 F3 107.2(2) . . ?
F2 C22 F1 107.3(2) . . ?
F3 C22 F1 107.0(2) . . ?
F2 C22 S3 112.21(17) . . ?
F3 C22 S3 111.78(17) . . ?
F1 C22 S3 111.12(18) . . ?
C7 N1 C2 114.88(16) . . ?
C7 N1 C18 122.87(16) . . ?
C2 N1 C18 122.15(15) . . ?
C11 N2 C17 114.24(16) . . ?
C11 N2 C20 123.79(16) . . ?
C17 N2 C20 121.86(16) . . ?
C7 S1 C1 91.47(9) . . ?
C11 S2 C12 91.17(9) . . ?
O3 S3 O2 114.70(10) . . ?
O3 S3 O1 115.14(9) . . ?
O2 S3 O1 115.22(9) . . ?
O3 S3 C22 103.47(11) . . ?
O2 S3 C22 103.38(11) . . ?
O1 S3 C22 102.46(10) . . ?

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
C6 C1 C2 C3 -0.4(3) . . . . ?
S1 C1 C2 C3 -179.93(15) . . . . ?
C6 C1 C2 N1 178.76(17) . . . . ?
S1 C1 C2 N1 -0.7(2) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
N1 C2 C3 C4 -178.33(18) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
S1 C1 C6 C5 179.34(16) . . . . ?
N1 C7 C8 C9 179.80(18) . . . . ?
S1 C7 C8 C9 -0.4(3) . . . . ?
C7 C8 C9 C10 178.08(19) . . . . ?
C8 C9 C10 C11 178.18(19) . . . . ?
C9 C10 C11 N2 168.42(19) . . . . ?
C9 C10 C11 S2 -12.7(3) . . . . ?
C17 C12 C13 C14 0.7(3) . . . . ?
S2 C12 C13 C14 -176.99(15) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C14 C15 C16 C17 0.7(3) . . . . ?
C15 C16 C17 C12 -0.5(3) . . . . ?
C15 C16 C17 N2 179.89(19) . . . . ?
C13 C12 C17 C16 -0.2(3) . . . . ?
S2 C12 C17 C16 177.87(16) . . . . ?
C13 C12 C17 N2 179.45(17) . . . . ?
S2 C12 C17 N2 -2.5(2) . . . . ?
C8 C7 N1 C2 177.84(18) . . . . ?
S1 C7 N1 C2 -2.0(2) . . . . ?
C8 C7 N1 C18 1.4(3) . . . . ?
S1 C7 N1 C18 -178.44(14) . . . . ?
C3 C2 N1 C7 -179.09(18) . . . . ?
C1 C2 N1 C7 1.8(2) . . . . ?
C3 C2 N1 C18 -2.6(3) . . . . ?
C1 C2 N1 C18 178.28(16) . . . . ?
C19 C18 N1 C7 84.3(2) . . . . ?
C19 C18 N1 C2 -91.9(2) . . . . ?
C10 C11 N2 C17 177.33(18) . . . . ?
S2 C11 N2 C17 -1.6(2) . . . . ?
C10 C11 N2 C20 -6.3(3) . . . . ?
S2 C11 N2 C20 174.70(15) . . . . ?
C16 C17 N2 C11 -177.67(19) . . . . ?
C12 C17 N2 C11 2.7(2) . . . . ?
C16 C17 N2 C20 5.9(3) . . . . ?
C12 C17 N2 C20 -173.71(17) . . . . ?
C21 C20 N2 C11 95.4(2) . . . . ?
C21 C20 N2 C17 -88.6(2) . . . . ?
N1 C7 S1 C1 1.26(14) . . . . ?
C8 C7 S1 C1 -178.54(18) . . . . ?
C6 C1 S1 C7 -179.74(19) . . . . ?
C2 C1 S1 C7 -0.28(15) . . . . ?
N2 C11 S2 C12 0.16(15) . . . . ?
C10 C11 S2 C12 -178.83(17) . . . . ?
C17 C12 S2 C11 1.34(15) . . . . ?
C13 C12 S2 C11 179.24(18) . . . . ?
F2 C22 S3 O3 -55.2(2) . . . . ?
F3 C22 S3 O3 -175.67(17) . . . . ?
F1 C22 S3 O3 64.90(19) . . . . ?
F2 C22 S3 O2 64.7(2) . . . . ?
F3 C22 S3 O2 -55.76(19) . . . . ?
F1 C22 S3 O2 -175.19(17) . . . . ?
F2 C22 S3 O1 -175.23(18) . . . . ?
F3 C22 S3 O1 64.31(19) . . . . ?
F1 C22 S3 O1 -55.12(19) . . . . ?

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
C3 H3 O1_$1 0.95 2.57 3.497(3) 165.5 3_566
C10 H10 O2_$2 0.95 2.65 3.486(2) 147.1 4_565
C13 H13 O1_$3 0.95 2.48 3.277(3) 141.5 3_666
C18 H18A O3_$2 0.99 2.37 3.336(2) 164.3 4_565
C20 H20B F3 0.99 2.57 3.552(3) 174.1 .
C21 H21C F2_$4 0.98 2.52 3.224(3) 128.2 3_656

_refine_diff_density_max         0.358
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.057

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Cy3_NTf2
_database_code_depnum_ccdc_archive 'CCDC 1995224'
loop_
_audit_author_name
_audit_author_address
'David Pugh'
;Kings College London
United Kingdom
;
_audit_update_record             
;
2020-04-06 deposited with the CCDC.	2020-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N2 S2, C2 F6 N O4 S2'
_chemical_formula_sum            'C23 H21 F6 N3 O4 S4'
_chemical_formula_weight         645.67

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   14.7979(2)
_cell_length_b                   21.9313(3)
_cell_length_c                   18.0080(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.854(2)
_cell_angle_gamma                90
_cell_volume                     5385.47(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    173.00(14)
_cell_measurement_reflns_used    4482
_cell_measurement_theta_min      3.8020
_cell_measurement_theta_max      73.2580

_exptl_crystal_description       blade
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_F_000             2640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    3.964
_shelx_estimated_absorpt_T_min   0.383
_shelx_estimated_absorpt_T_max   0.858
_exptl_absorpt_correction_T_min  0.80748
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.802
_oxdiff_exptl_absorpt_empirical_full_max 1.291
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      173.00(14)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.4115
_diffrn_reflns_number            8357
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         6.377
_diffrn_reflns_theta_max         66.585
_diffrn_reflns_theta_full        66.585
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4679
_reflns_number_gt                3865
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    Olex-2
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-III, Mercury'
_computing_publication_material  'enCIFer, WinGX'

_refine_special_details          
;
The anisotropic parameters of O3 and O4 indicated the likely presence of
positional disorder. However, all attempts at modelling this did not
result in a satisfactory solution hence isotropic restraints were used
in order to retain sensible thermal parameters. This explains the level B
CheckCIF alerts PLAT230_ALERT_2_B.
 
One residual electron density peak of 1.72 eΑ⁻³ was located close to S3.
Attempts at modelling this as an atom were unsuccessful and it was not
possible to remove this using solvent masking.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1015P)²+23.1011P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4679
_refine_ls_number_parameters     365
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.1933
_refine_ls_wR_factor_gt          0.1802
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

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
C1 C 0.4347(3) 0.53202(18) 0.3715(2) 0.0261(8) Uani 1 1 d . . . . .
C2 C 0.4030(3) 0.47307(18) 0.3782(2) 0.0253(8) Uani 1 1 d . . . . .
C3 C 0.3036(3) 0.45920(19) 0.3492(2) 0.0301(8) Uani 1 1 d . . . . .
H3 H 0.281706 0.419190 0.353741 0.036 Uiso 1 1 calc R U . . .
C4 C 0.2373(3) 0.5057(2) 0.3133(2) 0.0327(9) Uani 1 1 d . . . . .
H4 H 0.169031 0.497178 0.291986 0.039 Uiso 1 1 calc R U . . .
C5 C 0.2690(3) 0.5644(2) 0.3079(2) 0.0350(9) Uani 1 1 d . . . . .
H5 H 0.221893 0.595480 0.283668 0.042 Uiso 1 1 calc R U . . .
C6 C 0.3682(3) 0.57879(19) 0.3371(2) 0.0303(8) Uani 1 1 d . . . . .
H6 H 0.389722 0.619107 0.333733 0.036 Uiso 1 1 calc R U . . .
C7 C 0.5715(3) 0.45815(17) 0.4357(2) 0.0248(8) Uani 1 1 d . . . . .
C8 C 0.6602(3) 0.42757(18) 0.4708(2) 0.0285(8) Uani 1 1 d . . . . .
H8 H 0.659093 0.384418 0.474914 0.034 Uiso 1 1 calc R U . . .
C9 C 0.750000 0.4566(2) 0.500000 0.0257(11) Uani 1 2 d S T P . .
H9 H 0.749999 0.499959 0.499999 0.031 Uiso 1 2 calc R U P . .
C10 C 0.4674(3) 0.36960(18) 0.4361(2) 0.0318(9) Uani 1 1 d . . . . .
H10A H 0.405637 0.366933 0.445090 0.038 Uiso 1 1 calc R U . . .
H10B H 0.521938 0.358181 0.487088 0.038 Uiso 1 1 calc R U . . .
C11 C 0.4634(4) 0.3251(2) 0.3715(3) 0.0464(11) Uani 1 1 d . . . . .
H11A H 0.403887 0.332246 0.323293 0.070 Uiso 1 1 calc R U . . .
H11B H 0.462518 0.283377 0.390834 0.070 Uiso 1 1 calc R U . . .
H11C H 0.521167 0.330503 0.358258 0.070 Uiso 1 1 calc R U . . .
C12 C 0.4440(3) 0.54507(19) 0.8788(2) 0.0331(9) Uani 1 1 d . . . . .
C13 C 0.4741(3) 0.48524(19) 0.8730(2) 0.0319(9) Uani 1 1 d . . . . .
C14 C 0.5437(3) 0.4740(2) 0.8405(2) 0.0380(10) Uani 1 1 d . . . . .
H14 H 0.564531 0.433591 0.836498 0.046 Uiso 1 1 calc R U . . .
C15 C 0.5818(4) 0.5232(3) 0.8140(3) 0.0456(12) Uani 1 1 d . . . . .
H15 H 0.629562 0.516324 0.791764 0.055 Uiso 1 1 calc R U . . .
C16 C 0.5516(4) 0.5824(3) 0.8194(3) 0.0500(13) Uani 1 1 d . . . . .
H16 H 0.578768 0.615307 0.800659 0.060 Uiso 1 1 calc R U . . .
C17 C 0.4823(4) 0.5940(2) 0.8518(3) 0.0425(11) Uani 1 1 d . . . . .
H17 H 0.461524 0.634534 0.855316 0.051 Uiso 1 1 calc R U . . .
C18 C 0.3634(3) 0.46685(18) 0.9324(2) 0.0279(8) Uani 1 1 d . . . . .
C19 C 0.3081(3) 0.43461(18) 0.9665(2) 0.0291(8) Uani 1 1 d . . . . .
H19 H 0.310239 0.391318 0.966717 0.035 Uiso 1 1 calc R U . . .
C20 C 0.250000 0.4639(2) 1.000000 0.0281(11) Uani 1 2 d S T P . .
H20 H 0.250001 0.507239 0.999999 0.034 Uiso 1 2 calc R U P . .
C21 C 0.4443(3) 0.37657(18) 0.9009(2) 0.0337(9) Uani 1 1 d . . . . .
H21A H 0.429298 0.355689 0.943484 0.040 Uiso 1 1 calc R U . . .
H21B H 0.514043 0.369046 0.911024 0.040 Uiso 1 1 calc R U . . .
C22 C 0.3798(4) 0.3509(2) 0.8191(3) 0.0468(11) Uani 1 1 d . . . . .
H22A H 0.394941 0.371423 0.776961 0.070 Uiso 1 1 calc R U . . .
H22B H 0.310690 0.357566 0.809592 0.070 Uiso 1 1 calc R U . . .
H22C H 0.392088 0.307053 0.817850 0.070 Uiso 1 1 calc R U . . .
C23 C 0.4135(3) 0.2676(2) 0.6187(3) 0.0461(12) Uani 1 1 d . . . . .
C24 C 0.8028(5) 0.2282(3) 0.6518(4) 0.0644(16) Uani 1 1 d . . . . .
N1 N 0.4816(2) 0.43303(15) 0.41574(18) 0.0261(7) Uani 1 1 d . . . . .
N2 N 0.4275(2) 0.44279(15) 0.90386(19) 0.0296(7) Uani 1 1 d . . . . .
N3 N 0.250000 0.3052(2) 0.500000 0.0457(14) Uani 1 2 d S T P . .
N4 N 0.750000 0.2689(3) 0.500000 0.0517(15) Uani 1 2 d S T P . .
O1 O 0.2645(3) 0.3117(2) 0.6391(3) 0.0737(14) Uani 1 1 d . . . . .
O2 O 0.2513(3) 0.20981(17) 0.5816(2) 0.0562(10) Uani 1 1 d . . . . .
O3 O 0.6421(3) 0.2836(3) 0.5734(3) 0.0907(17) Uani 1 1 d . U . . .
O4 O 0.6655(5) 0.1810(3) 0.5323(4) 0.116(2) Uani 1 1 d . U . . .
F1 F 0.4507(2) 0.24049(15) 0.68969(19) 0.0618(8) Uani 1 1 d . . . . .
F2 F 0.4528(2) 0.32267(17) 0.6269(3) 0.0892(14) Uani 1 1 d . . . . .
F3 F 0.4400(2) 0.2362(2) 0.5675(2) 0.0788(12) Uani 1 1 d . . . . .
F4 F 0.7710(3) 0.1987(2) 0.7011(3) 0.0981(14) Uani 1 1 d . . . . .
F5 F 0.8372(3) 0.2814(2) 0.6839(3) 0.0832(11) Uani 1 1 d . . . . .
F6 F 0.8773(3) 0.1986(2) 0.6469(2) 0.0994(16) Uani 1 1 d . . . . .
S1 S 0.56257(7) 0.53513(4) 0.40929(6) 0.0273(3) Uani 1 1 d . . . . .
S2 S 0.35713(8) 0.54600(4) 0.92172(6) 0.0333(3) Uani 1 1 d . . . . .
S3 S 0.28025(7) 0.27165(5) 0.58369(7) 0.0377(3) Uani 1 1 d . . . . .
S4 S 0.70105(10) 0.23859(7) 0.55542(10) 0.0658(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C6 1.390(6) . ?
C1 C2 1.396(5) . ?
C1 S1 1.746(4) . ?
C2 C3 1.390(5) . ?
C2 N1 1.404(5) . ?
C3 C4 1.389(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.353(5) . ?
C7 C8 1.389(5) . ?
C7 S1 1.745(4) . ?
C8 C9 1.380(5) . ?
C8 H8 0.9500 . ?
C9 C8 1.380(5) 2_656 ?
C9 H9 0.9500 . ?
C10 N1 1.474(5) . ?
C10 C11 1.503(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.388(6) . ?
C12 C13 1.403(6) . ?
C12 S2 1.738(5) . ?
C13 C14 1.390(6) . ?
C13 N2 1.395(5) . ?
C14 C15 1.386(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(8) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 N2 1.349(5) . ?
C18 C19 1.391(6) . ?
C18 S2 1.745(4) . ?
C19 C20 1.386(5) . ?
C19 H19 0.9500 . ?
C20 C19 1.386(5) 2_557 ?
C20 H20 0.9500 . ?
C21 N2 1.478(5) . ?
C21 C22 1.519(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 F1 1.322(6) . ?
C23 F2 1.323(6) . ?
C23 F3 1.324(7) . ?
C23 S3 1.825(5) . ?
C24 F6 1.311(7) . ?
C24 F5 1.314(8) . ?
C24 F4 1.325(8) . ?
C24 S4 1.816(6) . ?
N3 S3 1.578(3) . ?
N3 S3 1.578(3) 2_556 ?
N4 S4 1.588(3) 2_656 ?
N4 S4 1.589(3) . ?
O1 S3 1.415(4) . ?
O2 S3 1.419(4) . ?
O3 S4 1.434(5) . ?
O4 S4 1.370(7) . ?

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
C6 C1 C2 121.2(4) . . ?
C6 C1 S1 128.2(3) . . ?
C2 C1 S1 110.6(3) . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 N1 127.0(4) . . ?
C1 C2 N1 112.2(3) . . ?
C4 C3 C2 117.8(4) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C5 C4 C3 121.2(4) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 117.6(4) . . ?
C5 C6 H6 121.2 . . ?
C1 C6 H6 121.2 . . ?
N1 C7 C8 125.6(3) . . ?
N1 C7 S1 111.0(3) . . ?
C8 C7 S1 123.3(3) . . ?
C9 C8 C7 123.4(4) . . ?
C9 C8 H8 118.3 . . ?
C7 C8 H8 118.3 . . ?
C8 C9 C8 125.0(5) 2_656 . ?
C8 C9 H9 117.5 2_656 . ?
C8 C9 H9 117.5 . . ?
N1 C10 C11 112.8(3) . . ?
N1 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
N1 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 120.8(4) . . ?
C17 C12 S2 128.3(4) . . ?
C13 C12 S2 110.8(3) . . ?
C14 C13 N2 127.6(4) . . ?
C14 C13 C12 120.4(4) . . ?
N2 C13 C12 112.0(4) . . ?
C15 C14 C13 118.3(5) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
C14 C15 C16 121.3(5) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 120.9(4) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C12 118.3(5) . . ?
C16 C17 H17 120.8 . . ?
C12 C17 H17 120.8 . . ?
N2 C18 C19 126.2(4) . . ?
N2 C18 S2 111.2(3) . . ?
C19 C18 S2 122.6(3) . . ?
C20 C19 C18 121.8(4) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C19 C20 C19 124.7(5) . 2_557 ?
C19 C20 H20 117.6 . . ?
C19 C20 H20 117.6 2_557 . ?
N2 C21 C22 110.4(3) . . ?
N2 C21 H21A 109.6 . . ?
C22 C21 H21A 109.6 . . ?
N2 C21 H21B 109.6 . . ?
C22 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F1 C23 F2 107.6(4) . . ?
F1 C23 F3 108.3(4) . . ?
F2 C23 F3 108.5(5) . . ?
F1 C23 S3 110.1(4) . . ?
F2 C23 S3 111.3(3) . . ?
F3 C23 S3 110.9(4) . . ?
F6 C24 F5 106.1(6) . . ?
F6 C24 F4 109.2(5) . . ?
F5 C24 F4 108.4(6) . . ?
F6 C24 S4 113.9(5) . . ?
F5 C24 S4 110.2(4) . . ?
F4 C24 S4 108.9(5) . . ?
C7 N1 C2 114.7(3) . . ?
C7 N1 C10 122.6(3) . . ?
C2 N1 C10 122.6(3) . . ?
C18 N2 C13 114.8(3) . . ?
C18 N2 C21 123.4(3) . . ?
C13 N2 C21 121.7(3) . . ?
S3 N3 S3 124.4(3) . 2_556 ?
S4 N4 S4 130.6(4) 2_656 . ?
C7 S1 C1 91.39(18) . . ?
C12 S2 C18 91.2(2) . . ?
O1 S3 O2 118.7(3) . . ?
O1 S3 N3 108.7(3) . . ?
O2 S3 N3 116.8(2) . . ?
O1 S3 C23 103.8(3) . . ?
O2 S3 C23 103.8(2) . . ?
N3 S3 C23 102.70(17) . . ?
O4 S4 O3 120.5(4) . . ?
O4 S4 N4 114.2(4) . . ?
O3 S4 N4 108.6(3) . . ?
O4 S4 C24 104.6(4) . . ?
O3 S4 C24 102.8(3) . . ?
N4 S4 C24 104.0(2) . . ?

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
C6 C1 C2 C3 1.3(6) . . . . ?
S1 C1 C2 C3 -177.6(3) . . . . ?
C6 C1 C2 N1 -179.1(3) . . . . ?
S1 C1 C2 N1 2.0(4) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
N1 C2 C3 C4 -179.5(4) . . . . ?
C2 C3 C4 C5 -1.2(6) . . . . ?
C3 C4 C5 C6 0.9(6) . . . . ?
C4 C5 C6 C1 0.5(6) . . . . ?
C2 C1 C6 C5 -1.6(6) . . . . ?
S1 C1 C6 C5 177.1(3) . . . . ?
N1 C7 C8 C9 -170.9(3) . . . . ?
S1 C7 C8 C9 10.7(5) . . . . ?
C7 C8 C9 C8 -174.5(4) . . . 2_656 ?
C17 C12 C13 C14 0.5(6) . . . . ?
S2 C12 C13 C14 -179.9(3) . . . . ?
C17 C12 C13 N2 179.7(4) . . . . ?
S2 C12 C13 N2 -0.7(4) . . . . ?
N2 C13 C14 C15 -179.2(4) . . . . ?
C12 C13 C14 C15 -0.2(6) . . . . ?
C13 C14 C15 C16 -0.2(6) . . . . ?
C14 C15 C16 C17 0.2(7) . . . . ?
C15 C16 C17 C12 0.1(7) . . . . ?
C13 C12 C17 C16 -0.5(6) . . . . ?
S2 C12 C17 C16 180.0(3) . . . . ?
N2 C18 C19 C20 174.7(3) . . . . ?
S2 C18 C19 C20 -5.2(5) . . . . ?
C18 C19 C20 C19 178.8(4) . . . 2_557 ?
C8 C7 N1 C2 -177.8(4) . . . . ?
S1 C7 N1 C2 0.8(4) . . . . ?
C8 C7 N1 C10 5.7(6) . . . . ?
S1 C7 N1 C10 -175.7(3) . . . . ?
C3 C2 N1 C7 177.8(4) . . . . ?
C1 C2 N1 C7 -1.9(5) . . . . ?
C3 C2 N1 C10 -5.7(6) . . . . ?
C1 C2 N1 C10 174.7(3) . . . . ?
C11 C10 N1 C7 -90.1(5) . . . . ?
C11 C10 N1 C2 93.6(4) . . . . ?
C19 C18 N2 C13 -179.7(4) . . . . ?
S2 C18 N2 C13 0.3(4) . . . . ?
C19 C18 N2 C21 3.4(6) . . . . ?
S2 C18 N2 C21 -176.6(3) . . . . ?
C14 C13 N2 C18 179.4(4) . . . . ?
C12 C13 N2 C18 0.3(5) . . . . ?
C14 C13 N2 C21 -3.7(6) . . . . ?
C12 C13 N2 C21 177.2(3) . . . . ?
C22 C21 N2 C18 93.9(5) . . . . ?
C22 C21 N2 C13 -82.8(5) . . . . ?
N1 C7 S1 C1 0.3(3) . . . . ?
C8 C7 S1 C1 179.0(3) . . . . ?
C6 C1 S1 C7 179.8(4) . . . . ?
C2 C1 S1 C7 -1.4(3) . . . . ?
C17 C12 S2 C18 -179.7(4) . . . . ?
C13 C12 S2 C18 0.7(3) . . . . ?
N2 C18 S2 C12 -0.6(3) . . . . ?
C19 C18 S2 C12 179.4(3) . . . . ?
S3 N3 S3 O1 -156.8(2) 2_556 . . . ?
S3 N3 S3 O2 -19.2(2) 2_556 . . . ?
S3 N3 S3 C23 93.60(19) 2_556 . . . ?
F1 C23 S3 O1 66.4(4) . . . . ?
F2 C23 S3 O1 -52.8(5) . . . . ?
F3 C23 S3 O1 -173.7(4) . . . . ?
F1 C23 S3 O2 -58.3(4) . . . . ?
F2 C23 S3 O2 -177.6(4) . . . . ?
F3 C23 S3 O2 61.5(4) . . . . ?
F1 C23 S3 N3 179.6(4) . . . . ?
F2 C23 S3 N3 60.4(5) . . . . ?
F3 C23 S3 N3 -60.5(4) . . . . ?
S4 N4 S4 O4 -25.0(3) 2_656 . . . ?
S4 N4 S4 O3 -162.6(3) 2_656 . . . ?
S4 N4 S4 C24 88.4(2) 2_656 . . . ?
F6 C24 S4 O4 67.0(6) . . . . ?
F5 C24 S4 O4 -173.9(5) . . . . ?
F4 C24 S4 O4 -55.1(6) . . . . ?
F6 C24 S4 O3 -166.3(5) . . . . ?
F5 C24 S4 O3 -47.2(5) . . . . ?
F4 C24 S4 O3 71.6(5) . . . . ?
F6 C24 S4 N4 -53.1(6) . . . . ?
F5 C24 S4 N4 66.0(5) . . . . ?
F4 C24 S4 N4 -175.2(5) . . . . ?

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
C3 H3 O1_$1 0.95 2.47 3.420(6) 174.9 2_556
C6 H6 F2_$2 0.95 2.51 3.283(5) 139.0 5_666
C10 H10B O3 0.99 2.47 3.375(6) 151.5 .
C19 H19 O2_$3 0.95 2.43 3.311(5) 154.8 7_556

_refine_diff_density_max         1.715
_refine_diff_density_min         -1.421
_refine_diff_density_rms         0.098

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Cy3_PF6
_database_code_depnum_ccdc_archive 'CCDC 1995226'
loop_
_audit_author_name
_audit_author_address
'David Pugh'
;Kings College London
United Kingdom
;
_audit_update_record             
;
2020-04-06 deposited with the CCDC.	2020-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N2 S2, F6 P'
_chemical_formula_sum            'C21 H21 F6 N2 P S2'
_chemical_formula_weight         510.49

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'
N N 0.0061 0.0033 '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'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.6864(8)
_cell_length_b                   18.6880(8)
_cell_length_c                   15.7950(8)
_cell_angle_alpha                90
_cell_angle_beta                 114.792(6)
_cell_angle_gamma                90
_cell_volume                     4739.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    172.95(10)
_cell_measurement_reflns_used    4138
_cell_measurement_theta_min      2.5750
_cell_measurement_theta_max      27.1360

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             2096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.351
_shelx_estimated_absorpt_T_min   0.887
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_T_min  0.93008
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.929
_oxdiff_exptl_absorpt_empirical_full_max 1.061
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      172.95(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            12437
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.192
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4180
_reflns_number_gt                3390
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 Structure factors included contributions from the .fab file.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'Olex-2, WinGX, PLATON'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3, Mercury'
_computing_publication_material  ?
_refine_special_details          
;
The PF6 anion was disordered over two positions. Although this was
successfully modelled, many restraints (DFIX, DANG, EADP) were required
to retain a sensible geometry and thermal displacement ellipsoids.

A small amount of disordered solvent was also present and this could
not be modelled, hence it was removed using SQUEEZE. 203 electrons were
removed which corresponds to 0.5 molecules of CH2Cl2 per asymmetric
unit (this was the solvent used to recrystallise the sample).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1175P)²+14.4064P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4180
_refine_ls_number_parameters     313
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0660
_refine_ls_wR_factor_ref         0.2032
_refine_ls_wR_factor_gt          0.1906
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.121
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

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
C1 C 0.3289(2) 0.8228(2) 0.3459(3) 0.0361(8) Uani 1 1 d . . . . .
C2 C 0.3232(2) 0.8823(2) 0.2903(3) 0.0429(9) Uani 1 1 d . . . . .
H2 H 0.331042 0.929441 0.315064 0.051 Uiso 1 1 calc R U . . .
C3 C 0.3056(3) 0.8699(2) 0.1978(3) 0.0472(10) Uani 1 1 d . . . . .
H3 H 0.301770 0.909265 0.158145 0.057 Uiso 1 1 calc R U . . .
C4 C 0.2935(2) 0.8008(2) 0.1613(3) 0.0467(10) Uani 1 1 d . . . . .
H4 H 0.279677 0.794011 0.096910 0.056 Uiso 1 1 calc R U . . .
C5 C 0.3011(2) 0.7422(2) 0.2170(3) 0.0421(9) Uani 1 1 d . . . . .
H5 H 0.294108 0.695032 0.192387 0.051 Uiso 1 1 calc R U . . .
C6 C 0.3194(2) 0.7541(2) 0.3107(2) 0.0348(8) Uani 1 1 d . . . . .
C7 C 0.3468(2) 0.7293(2) 0.4645(2) 0.0338(8) Uani 1 1 d . . . . .
C8 C 0.3590(2) 0.6873(2) 0.5426(3) 0.0386(8) Uani 1 1 d . . . . .
H8 H 0.354326 0.636806 0.534785 0.046 Uiso 1 1 calc R U . . .
C9 C 0.3775(2) 0.7146(2) 0.6308(3) 0.0387(8) Uani 1 1 d . . . . .
H9 H 0.384474 0.764848 0.640206 0.046 Uiso 1 1 calc R U . . .
C10 C 0.3863(2) 0.6715(2) 0.7055(3) 0.0380(8) Uani 1 1 d . . . . .
H10 H 0.379773 0.621379 0.694845 0.046 Uiso 1 1 calc R U . . .
C11 C 0.4039(2) 0.6959(2) 0.7949(3) 0.0350(8) Uani 1 1 d . . . . .
C12 C 0.4349(2) 0.7636(2) 0.9415(3) 0.0449(10) Uani 1 1 d . . . . .
C13 C 0.4512(3) 0.8099(3) 1.0162(4) 0.0590(12) Uani 1 1 d . . . . .
H13 H 0.456103 0.859988 1.009867 0.071 Uiso 1 1 calc R U . . .
C14 C 0.4600(3) 0.7802(4) 1.1000(3) 0.0694(16) Uani 1 1 d . . . . .
H14 H 0.471562 0.810326 1.152400 0.083 Uiso 1 1 calc R U . . .
C15 C 0.4522(3) 0.7072(3) 1.1083(3) 0.0617(13) Uani 1 1 d . . . . .
H15 H 0.458722 0.688087 1.166726 0.074 Uiso 1 1 calc R U . . .
C16 C 0.4353(2) 0.6615(3) 1.0344(3) 0.0496(10) Uani 1 1 d . . . . .
H16 H 0.429625 0.611524 1.040722 0.060 Uiso 1 1 calc R U . . .
C17 C 0.4268(2) 0.6908(2) 0.9502(3) 0.0399(9) Uani 1 1 d . . . . .
C18 C 0.3282(3) 0.6251(2) 0.3605(3) 0.0443(9) Uani 1 1 d . . . . .
H18A H 0.371152 0.600643 0.415107 0.053 Uiso 1 1 calc R U . . .
H18B H 0.341464 0.616770 0.306304 0.053 Uiso 1 1 calc R U . . .
C19 C 0.2435(3) 0.5932(2) 0.3405(3) 0.0561(11) Uani 1 1 d . . . . .
H19A H 0.231568 0.598864 0.395392 0.084 Uiso 1 1 calc R U . . .
H19B H 0.243559 0.542177 0.326065 0.084 Uiso 1 1 calc R U . . .
H19C H 0.200688 0.617848 0.287215 0.084 Uiso 1 1 calc R U . . .
C20 C 0.3961(2) 0.5761(2) 0.8580(3) 0.0391(8) Uani 1 1 d . . . . .
H20A H 0.353282 0.564482 0.794909 0.047 Uiso 1 1 calc R U . . .
H20B H 0.375396 0.559465 0.903958 0.047 Uiso 1 1 calc R U . . .
C21 C 0.4760(2) 0.5368(2) 0.8742(3) 0.0440(9) Uani 1 1 d . . . . .
H21A H 0.498555 0.555266 0.831432 0.066 Uiso 1 1 calc R U . . .
H21B H 0.464452 0.485559 0.862976 0.066 Uiso 1 1 calc R U . . .
H21C H 0.516703 0.544248 0.938721 0.066 Uiso 1 1 calc R U . . .
N1 N 0.33091(18) 0.70224(16) 0.3793(2) 0.0358(7) Uani 1 1 d . . . . .
N2 N 0.40834(17) 0.65373(17) 0.8664(2) 0.0361(7) Uani 1 1 d . . . . .
F1A F 0.7670(11) 0.4068(9) 0.9804(11) 0.0873(14) Uani 0.207(6) 1 d D . P A 1
F2A F 0.7673(14) 0.4436(12) 0.8470(15) 0.1107(17) Uani 0.207(6) 1 d D . P A 1
F3A F 0.6469(10) 0.4158(9) 0.8525(11) 0.0982(18) Uani 0.207(6) 1 d D . P A 1
F4A F 0.7937(11) 0.5221(10) 0.9622(15) 0.139(2) Uani 0.207(6) 1 d D U P A 1
F5A F 0.6751(13) 0.4920(12) 0.9710(13) 0.0687(11) Uani 0.207(6) 1 d D . P A 1
F6A F 0.6750(12) 0.5276(8) 0.8362(13) 0.118(2) Uani 0.207(6) 1 d D U P A 1
P1A P 0.7212(8) 0.4670(7) 0.9094(9) 0.0485(5) Uani 0.207(6) 1 d D . P A 1
F1B F 0.7381(3) 0.3821(2) 0.9559(4) 0.0873(14) Uani 0.793(6) 1 d D . P A 2
F2B F 0.7816(4) 0.4398(4) 0.8652(4) 0.1107(17) Uani 0.793(6) 1 d D . P A 2
F3B F 0.6463(3) 0.4524(3) 0.8346(3) 0.0982(18) Uani 0.793(6) 1 d D . P A 2
F4B F 0.8171(3) 0.4764(4) 1.0128(4) 0.139(2) Uani 0.793(6) 1 d D U P A 2
F5B F 0.6816(4) 0.4826(3) 0.9858(4) 0.0687(11) Uani 0.793(6) 1 d D . P A 2
F6B F 0.7379(4) 0.5406(2) 0.9015(5) 0.118(2) Uani 0.793(6) 1 d D U P A 2
P1B P 0.7314(2) 0.46080(16) 0.92571(19) 0.0485(5) Uani 0.793(6) 1 d D . P A 2
S1 S 0.34814(6) 0.82200(5) 0.46393(6) 0.0380(3) Uani 1 1 d . . . . .
S2 S 0.42304(6) 0.78495(6) 0.82905(7) 0.0456(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C6 1.380(5) . ?
C1 C2 1.395(5) . ?
C1 S1 1.749(4) . ?
C2 C3 1.380(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(5) . ?
C5 H5 0.9500 . ?
C6 N1 1.404(4) . ?
C7 N1 1.352(5) . ?
C7 C8 1.401(5) . ?
C7 S1 1.733(4) . ?
C8 C9 1.388(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(5) . ?
C10 H10 0.9500 . ?
C11 N2 1.352(5) . ?
C11 S2 1.738(4) . ?
C12 C17 1.381(6) . ?
C12 C13 1.392(6) . ?
C12 S2 1.745(4) . ?
C13 C14 1.381(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.374(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(6) . ?
C16 H16 0.9500 . ?
C17 N2 1.405(5) . ?
C18 N1 1.469(5) . ?
C18 C19 1.518(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 N2 1.465(5) . ?
C20 C21 1.516(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
F1A P1A 1.554(8) . ?
F2A P1A 1.580(8) . ?
F3A P1A 1.569(8) . ?
F4A P1A 1.582(8) . ?
F5A P1A 1.580(8) . ?
F6A P1A 1.581(8) . ?
F1B P1B 1.535(4) . ?
F2B P1B 1.601(4) . ?
F3B P1B 1.595(4) . ?
F4B P1B 1.589(4) . ?
F5B P1B 1.593(3) . ?
F6B P1B 1.556(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
C6 C1 C2 121.6(4) . . ?
C6 C1 S1 111.0(3) . . ?
C2 C1 S1 127.4(3) . . ?
C3 C2 C1 117.2(4) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 121.4(4) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 121.1(4) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 117.9(4) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C1 C6 C5 120.8(3) . . ?
C1 C6 N1 112.2(3) . . ?
C5 C6 N1 127.1(4) . . ?
N1 C7 C8 124.0(3) . . ?
N1 C7 S1 111.5(2) . . ?
C8 C7 S1 124.6(3) . . ?
C9 C8 C7 124.2(4) . . ?
C9 C8 H8 117.9 . . ?
C7 C8 H8 117.9 . . ?
C10 C9 C8 122.4(4) . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C9 C10 C11 125.0(4) . . ?
C9 C10 H10 117.5 . . ?
C11 C10 H10 117.5 . . ?
N2 C11 C10 124.6(4) . . ?
N2 C11 S2 111.3(3) . . ?
C10 C11 S2 124.1(3) . . ?
C17 C12 C13 121.4(4) . . ?
C17 C12 S2 110.6(3) . . ?
C13 C12 S2 128.0(4) . . ?
C14 C13 C12 117.6(5) . . ?
C14 C13 H13 121.2 . . ?
C12 C13 H13 121.2 . . ?
C13 C14 C15 120.8(4) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 121.7(5) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C17 117.9(5) . . ?
C15 C16 H16 121.1 . . ?
C17 C16 H16 121.1 . . ?
C12 C17 C16 120.6(4) . . ?
C12 C17 N2 112.7(3) . . ?
C16 C17 N2 126.6(4) . . ?
N1 C18 C19 111.9(3) . . ?
N1 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
N1 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C21 111.8(3) . . ?
N2 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
N2 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C7 N1 C6 114.4(3) . . ?
C7 N1 C18 122.9(3) . . ?
C6 N1 C18 122.7(3) . . ?
C11 N2 C17 114.0(3) . . ?
C11 N2 C20 123.2(3) . . ?
C17 N2 C20 122.8(3) . . ?
F1A P1A F3A 91.7(6) . . ?
F1A P1A F5A 90.9(6) . . ?
F3A P1A F5A 90.5(6) . . ?
F1A P1A F2A 90.1(6) . . ?
F3A P1A F2A 90.0(6) . . ?
F5A P1A F2A 178.8(7) . . ?
F1A P1A F6A 179.3(7) . . ?
F3A P1A F6A 88.1(6) . . ?
F5A P1A F6A 89.8(6) . . ?
F2A P1A F6A 89.2(6) . . ?
F1A P1A F4A 91.7(6) . . ?
F3A P1A F4A 176.6(7) . . ?
F5A P1A F4A 89.7(6) . . ?
F2A P1A F4A 89.7(6) . . ?
F6A P1A F4A 88.5(6) . . ?
F1B P1B F6B 172.1(4) . . ?
F1B P1B F4B 89.1(3) . . ?
F6B P1B F4B 84.0(3) . . ?
F1B P1B F5B 92.8(2) . . ?
F6B P1B F5B 91.0(3) . . ?
F4B P1B F5B 90.1(3) . . ?
F1B P1B F3B 96.1(3) . . ?
F6B P1B F3B 90.7(3) . . ?
F4B P1B F3B 174.6(4) . . ?
F5B P1B F3B 90.9(2) . . ?
F1B P1B F2B 87.8(3) . . ?
F6B P1B F2B 88.4(3) . . ?
F4B P1B F2B 89.7(3) . . ?
F5B P1B F2B 179.4(3) . . ?
F3B P1B F2B 89.2(3) . . ?
C7 S1 C1 90.95(17) . . ?
C11 S2 C12 91.23(19) . . ?

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
C6 C1 C2 C3 1.5(5) . . . . ?
S1 C1 C2 C3 -178.6(3) . . . . ?
C1 C2 C3 C4 0.5(6) . . . . ?
C2 C3 C4 C5 -2.1(6) . . . . ?
C3 C4 C5 C6 1.5(6) . . . . ?
C2 C1 C6 C5 -2.1(5) . . . . ?
S1 C1 C6 C5 178.1(3) . . . . ?
C2 C1 C6 N1 177.5(3) . . . . ?
S1 C1 C6 N1 -2.3(4) . . . . ?
C4 C5 C6 C1 0.5(5) . . . . ?
C4 C5 C6 N1 -179.1(3) . . . . ?
N1 C7 C8 C9 178.2(3) . . . . ?
S1 C7 C8 C9 -3.0(5) . . . . ?
C7 C8 C9 C10 177.7(3) . . . . ?
C8 C9 C10 C11 -179.3(3) . . . . ?
C9 C10 C11 N2 176.7(3) . . . . ?
C9 C10 C11 S2 -3.4(5) . . . . ?
C17 C12 C13 C14 0.8(6) . . . . ?
S2 C12 C13 C14 -178.5(3) . . . . ?
C12 C13 C14 C15 -0.5(7) . . . . ?
C13 C14 C15 C16 -0.2(7) . . . . ?
C14 C15 C16 C17 0.5(6) . . . . ?
C13 C12 C17 C16 -0.5(5) . . . . ?
S2 C12 C17 C16 178.9(3) . . . . ?
C13 C12 C17 N2 178.4(3) . . . . ?
S2 C12 C17 N2 -2.1(4) . . . . ?
C15 C16 C17 C12 -0.2(5) . . . . ?
C15 C16 C17 N2 -178.9(3) . . . . ?
C8 C7 N1 C6 179.0(3) . . . . ?
S1 C7 N1 C6 0.1(4) . . . . ?
C8 C7 N1 C18 -2.6(5) . . . . ?
S1 C7 N1 C18 178.5(3) . . . . ?
C1 C6 N1 C7 1.4(4) . . . . ?
C5 C6 N1 C7 -178.9(3) . . . . ?
C1 C6 N1 C18 -176.9(3) . . . . ?
C5 C6 N1 C18 2.7(5) . . . . ?
C19 C18 N1 C7 84.5(4) . . . . ?
C19 C18 N1 C6 -97.3(4) . . . . ?
C10 C11 N2 C17 -179.8(3) . . . . ?
S2 C11 N2 C17 0.2(4) . . . . ?
C10 C11 N2 C20 0.9(5) . . . . ?
S2 C11 N2 C20 -179.1(2) . . . . ?
C12 C17 N2 C11 1.3(4) . . . . ?
C16 C17 N2 C11 -179.9(3) . . . . ?
C12 C17 N2 C20 -179.4(3) . . . . ?
C16 C17 N2 C20 -0.6(5) . . . . ?
C21 C20 N2 C11 85.9(4) . . . . ?
C21 C20 N2 C17 -93.4(4) . . . . ?
N1 C7 S1 C1 -1.2(3) . . . . ?
C8 C7 S1 C1 179.9(3) . . . . ?
C6 C1 S1 C7 2.0(3) . . . . ?
C2 C1 S1 C7 -177.8(3) . . . . ?
N2 C11 S2 C12 -1.2(3) . . . . ?
C10 C11 S2 C12 178.9(3) . . . . ?
C17 C12 S2 C11 1.9(3) . . . . ?
C13 C12 S2 C11 -178.7(4) . . . . ?

_refine_diff_density_max         1.073
_refine_diff_density_min         -0.892
_refine_diff_density_rms         0.084



