# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_shelx
_audit_block_doi                 10.5517/cc141prm
_database_code_depnum_ccdc_archive 'CCDC 1044320'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acscatal.5b00243 2015
_audit_update_record             
;
2015-09-18 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H28 Cl3 F3 N2 O3 S'
_chemical_formula_weight         780.05

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'
Cl Cl 0.1484 0.1585 '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                   15.961(7)
_cell_length_b                   9.628(4)
_cell_length_c                   24.030(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.677(9)
_cell_angle_gamma                90
_cell_volume                     3588(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    6323
_cell_measurement_theta_min      1.394
_cell_measurement_theta_max      25.000

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             1600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.372
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            82361
_diffrn_reflns_av_unetI/netI     0.2263
_diffrn_reflns_av_R_equivalents  0.3718
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.394
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             6323
_reflns_number_gt                2103
_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       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-3
_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)+(0.2000P)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     SHELXL
_refine_ls_extinction_coef       0.021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6323
_refine_ls_number_parameters     470
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.3457
_refine_ls_R_factor_gt           0.1452
_refine_ls_wR_factor_ref         0.4242
_refine_ls_wR_factor_gt          0.3339
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.175
_refine_ls_shift/su_mean         0.016

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 1.0131(6) 0.3117(8) 0.3030(4) 0.053(2) Uani 1 1 d . . . . .
C2 C 1.1067(7) 0.4179(11) 0.3932(4) 0.098(3) Uani 1 1 d . . . . .
H2A H 1.1678 0.4202 0.4090 0.147 Uiso 1 1 calc R U . . .
H2B H 1.0853 0.5111 0.3863 0.147 Uiso 1 1 calc R U . . .
H2C H 1.0789 0.3732 0.4197 0.147 Uiso 1 1 calc R U . . .
C3 C 1.1557(6) 0.2795(10) 0.3193(4) 0.071(3) Uani 1 1 d . . . . .
H3 H 1.2139 0.2811 0.3377 0.085 Uiso 1 1 calc R U . . .
C4 C 1.1207(6) 0.2191(8) 0.2693(4) 0.060(2) Uani 1 1 d . . . . .
C5 C 0.9720(6) 0.1939(8) 0.2119(3) 0.049(2) Uani 1 1 d . . . . .
C6 C 0.8851(6) 0.2278(9) 0.2096(3) 0.065(2) Uani 1 1 d . . . . .
C7 C 0.8616(6) 0.3061(8) 0.2540(4) 0.063(2) Uani 1 1 d . . . . .
C8 C 0.9244(6) 0.3470(8) 0.3018(4) 0.065(2) Uani 1 1 d . . . . .
C9 C 0.9071(5) 0.4210(10) 0.3515(3) 0.057(2) Uani 1 1 d . . . . .
C10 C 0.8974(6) 0.3554(10) 0.3996(4) 0.080(3) Uani 1 1 d . . . . .
H10 H 0.8980 0.2589 0.4014 0.096 Uiso 1 1 calc R U . . .
C11 C 0.8865(6) 0.4340(15) 0.4466(4) 0.096(3) Uani 1 1 d . . . . .
H11 H 0.8784 0.3882 0.4790 0.115 Uiso 1 1 calc R U . . .
C12 C 0.8874(7) 0.5724(14) 0.4460(5) 0.096(3) Uani 1 1 d . . . . .
H12 H 0.8814 0.6217 0.4782 0.115 Uiso 1 1 calc R U . . .
C13 C 0.8971(7) 0.6432(12) 0.3977(5) 0.097(3) Uani 1 1 d . . . . .
H13 H 0.8979 0.7397 0.3967 0.116 Uiso 1 1 calc R U . . .
C14 C 0.9057(6) 0.5640(13) 0.3505(4) 0.082(3) Uani 1 1 d . . . . .
H14 H 0.9106 0.6096 0.3173 0.098 Uiso 1 1 calc R U . . .
C15 C 0.7713(6) 0.3428(9) 0.2483(4) 0.058(2) Uani 1 1 d . . . . .
C16 C 0.7250(6) 0.2935(10) 0.2858(4) 0.075(3) Uani 1 1 d . . . . .
H16 H 0.7514 0.2411 0.3176 0.089 Uiso 1 1 calc R U . . .
C17 C 0.6366(8) 0.3246(12) 0.2744(5) 0.100(4) Uani 1 1 d . . . . .
H17 H 0.6046 0.2897 0.2990 0.120 Uiso 1 1 calc R U . . .
C18 C 0.5946(7) 0.4053(13) 0.2281(5) 0.093(3) Uani 1 1 d . . . . .
H18 H 0.5359 0.4236 0.2211 0.111 Uiso 1 1 calc R U . . .
C19 C 0.6439(8) 0.4564(10) 0.1933(5) 0.089(3) Uani 1 1 d . . . . .
H19 H 0.6186 0.5145 0.1631 0.107 Uiso 1 1 calc R U . . .
C20 C 0.7304(7) 0.4237(9) 0.2021(4) 0.076(3) Uani 1 1 d . . . . .
H20 H 0.7615 0.4565 0.1766 0.091 Uiso 1 1 calc R U . . .
C21 C 0.8252(6) 0.1728(8) 0.1623(4) 0.065(2) Uani 1 1 d . . . . .
H21 H 0.7665 0.1862 0.1586 0.077 Uiso 1 1 calc R U . . .
C22 C 0.8547(7) 0.0971(9) 0.1205(3) 0.075(3) Uani 1 1 d . . . . .
H22 H 0.8145 0.0609 0.0894 0.089 Uiso 1 1 calc R U . . .
C23 C 0.9405(6) 0.0753(9) 0.1242(4) 0.069(3) Uani 1 1 d . . . . .
H23 H 0.9573 0.0290 0.0946 0.082 Uiso 1 1 calc R U . . .
C24 C 1.0032(6) 0.1207(9) 0.1710(4) 0.062(2) Uani 1 1 d . . . . .
C25 C 1.0952(6) 0.0973(9) 0.1781(4) 0.062(2) Uani 1 1 d . . . . .
C26 C 1.1516(6) 0.1427(9) 0.2269(4) 0.065(2) Uani 1 1 d . . . . .
C27 C 1.2463(6) 0.1174(9) 0.2418(4) 0.064(2) Uani 1 1 d . . . . .
C28 C 1.2813(7) 0.0372(9) 0.2900(4) 0.079(3) Uani 1 1 d . . . . .
H28 H 1.2463 -0.0028 0.3115 0.094 Uiso 1 1 calc R U . . .
C29 C 1.3711(7) 0.0188(10) 0.3049(4) 0.078(3) Uani 1 1 d . . . . .
H29 H 1.3960 -0.0317 0.3377 0.094 Uiso 1 1 calc R U . . .
C30 C 1.4199(7) 0.0707(12) 0.2740(6) 0.090(3) Uani 1 1 d . . . . .
H30 H 1.4789 0.0535 0.2845 0.108 Uiso 1 1 calc R U . . .
C31 C 1.3870(7) 0.1514(12) 0.2257(5) 0.093(3) Uani 1 1 d . . . . .
H31 H 1.4231 0.1906 0.2047 0.111 Uiso 1 1 calc R U . . .
C32 C 1.3022(7) 0.1703(9) 0.2106(4) 0.078(3) Uani 1 1 d . . . . .
H32 H 1.2791 0.2212 0.1776 0.094 Uiso 1 1 calc R U . . .
C33 C 1.1212(6) 0.0170(10) 0.1328(4) 0.066(2) Uani 1 1 d . . . . .
C34 C 1.1192(6) -0.1256(12) 0.1334(4) 0.077(3) Uani 1 1 d . . . . .
H34 H 1.1062 -0.1724 0.1641 0.092 Uiso 1 1 calc R U . . .
C35 C 1.1373(6) -0.2018(11) 0.0865(5) 0.091(3) Uani 1 1 d . . . . .
H35 H 1.1355 -0.2983 0.0860 0.110 Uiso 1 1 calc R U . . .
C36 C 1.1572(7) -0.1287(16) 0.0426(4) 0.098(4) Uani 1 1 d . . . . .
H36 H 1.1682 -0.1763 0.0114 0.117 Uiso 1 1 calc R U . . .
C37 C 1.1610(7) 0.0099(14) 0.0437(4) 0.092(3) Uani 1 1 d . . . . .
H37 H 1.1750 0.0570 0.0134 0.110 Uiso 1 1 calc R U . . .
C38 C 1.1452(6) 0.0824(11) 0.0878(4) 0.084(3) Uani 1 1 d . . . . .
H38 H 1.1504 0.1787 0.0881 0.101 Uiso 1 1 calc R U . . .
C39 C 0.8574(8) 0.5820(14) 0.0392(5) 0.124(4) Uani 1 1 d . . . . .
H39 H 0.8141 0.5620 0.0038 0.148 Uiso 1 1 calc R U . . .
C40 C 0.599(2) 0.537(4) -0.0468(10) 0.30(2) Uani 1 1 d . U . . .
N1 N 1.0882(5) 0.3401(8) 0.3388(3) 0.076(2) Uani 1 1 d . . . . .
N2 N 1.0319(5) 0.2369(7) 0.2591(3) 0.0584(19) Uani 1 1 d . . . . .
O1 O 0.7293(8) 0.520(3) -0.0766(4) 0.383(16) Uani 1 1 d . . . . .
O2 O 0.6359(19) 0.7207(19) -0.0758(7) 0.414(16) Uani 1 1 d . . . . .
O3 O 0.6052(6) 0.5333(10) -0.1453(4) 0.156(4) Uani 1 1 d . . . . .
F1 F 0.603(3) 0.3855(19) -0.0499(9) 0.50(2) Uani 1 1 d . . . . .
F2 F 0.6283(6) 0.5390(15) 0.0086(4) 0.239(6) Uani 1 1 d . . . . .
F3 F 0.5248(9) 0.533(3) -0.0522(6) 0.424(18) Uani 1 1 d . . . . .
S1 S 0.6491(3) 0.5638(6) -0.09129(17) 0.163(2) Uani 1 1 d . U . . .
Cl1 Cl 0.9421(4) 0.6518(8) 0.0218(5) 0.355(6) Uani 1 1 d . . . . .
Cl2 Cl 0.8787(4) 0.4344(4) 0.0768(2) 0.233(3) Uani 1 1 d . . . . .
Cl3 Cl 0.8158(5) 0.7066(6) 0.0771(2) 0.262(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 N1 1.328(10) . ?
C1 N2 1.367(9) . ?
C1 C8 1.449(11) . ?
C2 N1 1.474(10) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.333(10) . ?
C3 N1 1.400(10) . ?
C3 H3 0.9300 . ?
C4 N2 1.391(10) . ?
C4 C26 1.434(11) . ?
C5 N2 1.363(9) . ?
C5 C24 1.394(11) . ?
C5 C6 1.414(11) . ?
C6 C21 1.405(11) . ?
C6 C7 1.426(12) . ?
C7 C8 1.392(11) . ?
C7 C15 1.458(11) . ?
C8 C9 1.471(11) . ?
C9 C10 1.357(11) . ?
C9 C14 1.377(12) . ?
C10 C11 1.405(13) . ?
C10 H10 0.9300 . ?
C11 C12 1.333(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(14) . ?
C12 H12 0.9300 . ?
C13 C14 1.401(13) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.378(12) . ?
C15 C20 1.387(11) . ?
C16 C17 1.404(13) . ?
C16 H16 0.9300 . ?
C17 C18 1.393(14) . ?
C17 H17 0.9300 . ?
C18 C19 1.367(14) . ?
C18 H18 0.9300 . ?
C19 C20 1.383(13) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.408(11) . ?
C21 H21 0.9300 . ?
C22 C23 1.368(11) . ?
C22 H22 0.9300 . ?
C23 C24 1.387(11) . ?
C23 H23 0.9300 . ?
C24 C25 1.455(12) . ?
C25 C26 1.369(11) . ?
C25 C33 1.473(11) . ?
C26 C27 1.490(12) . ?
C27 C32 1.391(12) . ?
C27 C28 1.393(11) . ?
C28 C29 1.403(12) . ?
C28 H28 0.9300 . ?
C29 C30 1.297(13) . ?
C29 H29 0.9300 . ?
C30 C31 1.393(14) . ?
C30 H30 0.9300 . ?
C31 C32 1.329(12) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 C34 1.374(12) . ?
C33 C38 1.381(11) . ?
C34 C35 1.428(12) . ?
C34 H34 0.9300 . ?
C35 C36 1.368(14) . ?
C35 H35 0.9300 . ?
C36 C37 1.335(14) . ?
C36 H36 0.9300 . ?
C37 C38 1.342(13) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 Cl1 1.650(12) . ?
C39 Cl2 1.676(13) . ?
C39 Cl3 1.731(13) . ?
C39 H39 0.9800 . ?
C40 F3 1.16(3) . ?
C40 F2 1.30(2) . ?
C40 F1 1.46(4) . ?
C40 S1 1.50(2) . ?
O1 S1 1.316(12) . ?
O2 S1 1.582(18) . ?
O3 S1 1.355(8) . ?

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
N1 C1 N2 106.2(7) . . ?
N1 C1 C8 133.8(8) . . ?
N2 C1 C8 119.9(8) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 N1 107.0(8) . . ?
C4 C3 H3 126.5 . . ?
N1 C3 H3 126.5 . . ?
C3 C4 N2 107.2(8) . . ?
C3 C4 C26 136.3(9) . . ?
N2 C4 C26 116.5(8) . . ?
N2 C5 C24 116.3(8) . . ?
N2 C5 C6 116.8(8) . . ?
C24 C5 C6 126.9(8) . . ?
C21 C6 C5 114.7(8) . . ?
C21 C6 C7 123.7(9) . . ?
C5 C6 C7 121.5(8) . . ?
C8 C7 C6 120.1(9) . . ?
C8 C7 C15 120.8(8) . . ?
C6 C7 C15 119.2(8) . . ?
C7 C8 C1 117.4(8) . . ?
C7 C8 C9 124.8(8) . . ?
C1 C8 C9 117.9(8) . . ?
C10 C9 C14 118.3(9) . . ?
C10 C9 C8 123.1(9) . . ?
C14 C9 C8 118.4(8) . . ?
C9 C10 C11 119.7(9) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 121.7(11) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 120.3(11) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 117.6(10) . . ?
C12 C13 H13 121.2 . . ?
C14 C13 H13 121.2 . . ?
C9 C14 C13 122.3(10) . . ?
C9 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
C16 C15 C20 119.5(9) . . ?
C16 C15 C7 121.8(8) . . ?
C20 C15 C7 118.6(9) . . ?
C15 C16 C17 118.0(10) . . ?
C15 C16 H16 121.0 . . ?
C17 C16 H16 121.0 . . ?
C18 C17 C16 123.0(11) . . ?
C18 C17 H17 118.5 . . ?
C16 C17 H17 118.5 . . ?
C19 C18 C17 116.9(10) . . ?
C19 C18 H18 121.6 . . ?
C17 C18 H18 121.5 . . ?
C18 C19 C20 121.5(10) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C15 121.0(10) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
C6 C21 C22 119.6(9) . . ?
C6 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C23 C22 C21 122.1(8) . . ?
C23 C22 H22 119.0 . . ?
C21 C22 H22 119.0 . . ?
C22 C23 C24 121.6(8) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C5 C24 C23 114.9(9) . . ?
C5 C24 C25 120.9(8) . . ?
C23 C24 C25 124.1(9) . . ?
C26 C25 C24 119.5(8) . . ?
C26 C25 C33 123.9(9) . . ?
C24 C25 C33 116.5(8) . . ?
C25 C26 C4 120.3(9) . . ?
C25 C26 C27 125.3(8) . . ?
C4 C26 C27 114.4(8) . . ?
C32 C27 C28 118.0(9) . . ?
C32 C27 C26 123.7(9) . . ?
C28 C27 C26 118.4(8) . . ?
C27 C28 C29 117.9(9) . . ?
C27 C28 H28 121.1 . . ?
C29 C28 H28 121.1 . . ?
C30 C29 C28 121.3(10) . . ?
C30 C29 H29 119.3 . . ?
C28 C29 H29 119.3 . . ?
C29 C30 C31 122.2(11) . . ?
C29 C30 H30 118.9 . . ?
C31 C30 H30 118.9 . . ?
C32 C31 C30 117.6(10) . . ?
C32 C31 H31 121.2 . . ?
C30 C31 H31 121.2 . . ?
C31 C32 C27 123.0(10) . . ?
C31 C32 H32 118.5 . . ?
C27 C32 H32 118.5 . . ?
C34 C33 C38 118.3(9) . . ?
C34 C33 C25 120.4(9) . . ?
C38 C33 C25 121.2(9) . . ?
C33 C34 C35 119.8(9) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C36 C35 C34 118.1(10) . . ?
C36 C35 H35 120.9 . . ?
C34 C35 H35 120.9 . . ?
C37 C36 C35 121.1(10) . . ?
C37 C36 H36 119.5 . . ?
C35 C36 H36 119.5 . . ?
C36 C37 C38 121.3(10) . . ?
C36 C37 H37 119.3 . . ?
C38 C37 H37 119.3 . . ?
C37 C38 C33 121.3(10) . . ?
C37 C38 H38 119.3 . . ?
C33 C38 H38 119.3 . . ?
Cl1 C39 Cl2 114.1(8) . . ?
Cl1 C39 Cl3 107.0(8) . . ?
Cl2 C39 Cl3 110.9(7) . . ?
Cl1 C39 H39 108.2 . . ?
Cl2 C39 H39 108.2 . . ?
Cl3 C39 H39 108.2 . . ?
F3 C40 F2 103(2) . . ?
F3 C40 F1 91(2) . . ?
F2 C40 F1 93(3) . . ?
F3 C40 S1 129(2) . . ?
F2 C40 S1 127(2) . . ?
F1 C40 S1 96(3) . . ?
C1 N1 C3 110.2(7) . . ?
C1 N1 C2 129.8(8) . . ?
C3 N1 C2 120.0(8) . . ?
C5 N2 C1 124.3(8) . . ?
C5 N2 C4 126.4(7) . . ?
C1 N2 C4 109.3(7) . . ?
O1 S1 O3 115.9(8) . . ?
O1 S1 C40 113.8(18) . . ?
O3 S1 C40 113.7(10) . . ?
O1 S1 O2 114.9(15) . . ?
O3 S1 O2 111.4(10) . . ?
C40 S1 O2 82.7(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C3 C4 N2 -2.5(9) . . . . ?
N1 C3 C4 C26 178.9(9) . . . . ?
N2 C5 C6 C21 -175.6(7) . . . . ?
C24 C5 C6 C21 4.2(12) . . . . ?
N2 C5 C6 C7 1.4(11) . . . . ?
C24 C5 C6 C7 -178.7(8) . . . . ?
C21 C6 C7 C8 174.6(7) . . . . ?
C5 C6 C7 C8 -2.1(12) . . . . ?
C21 C6 C7 C15 -5.7(12) . . . . ?
C5 C6 C7 C15 177.6(7) . . . . ?
C6 C7 C8 C1 2.4(11) . . . . ?
C15 C7 C8 C1 -177.3(7) . . . . ?
C6 C7 C8 C9 -176.4(8) . . . . ?
C15 C7 C8 C9 3.9(12) . . . . ?
N1 C1 C8 C7 175.3(8) . . . . ?
N2 C1 C8 C7 -2.2(11) . . . . ?
N1 C1 C8 C9 -5.8(14) . . . . ?
N2 C1 C8 C9 176.7(7) . . . . ?
C7 C8 C9 C10 94.6(11) . . . . ?
C1 C8 C9 C10 -84.3(10) . . . . ?
C7 C8 C9 C14 -89.4(10) . . . . ?
C1 C8 C9 C14 91.8(10) . . . . ?
C14 C9 C10 C11 -0.2(13) . . . . ?
C8 C9 C10 C11 175.9(8) . . . . ?
C9 C10 C11 C12 -1.6(15) . . . . ?
C10 C11 C12 C13 1.6(17) . . . . ?
C11 C12 C13 C14 0.1(16) . . . . ?
C10 C9 C14 C13 1.9(13) . . . . ?
C8 C9 C14 C13 -174.4(8) . . . . ?
C12 C13 C14 C9 -1.8(14) . . . . ?
C8 C7 C15 C16 -64.2(11) . . . . ?
C6 C7 C15 C16 116.1(9) . . . . ?
C8 C7 C15 C20 119.2(9) . . . . ?
C6 C7 C15 C20 -60.5(10) . . . . ?
C20 C15 C16 C17 1.7(12) . . . . ?
C7 C15 C16 C17 -174.8(8) . . . . ?
C15 C16 C17 C18 -1.5(14) . . . . ?
C16 C17 C18 C19 -0.9(15) . . . . ?
C17 C18 C19 C20 3.2(15) . . . . ?
C18 C19 C20 C15 -3.1(14) . . . . ?
C16 C15 C20 C19 0.5(12) . . . . ?
C7 C15 C20 C19 177.1(8) . . . . ?
C5 C6 C21 C22 -3.3(11) . . . . ?
C7 C6 C21 C22 179.8(8) . . . . ?
C6 C21 C22 C23 -0.2(13) . . . . ?
C21 C22 C23 C24 3.4(13) . . . . ?
N2 C5 C24 C23 178.4(7) . . . . ?
C6 C5 C24 C23 -1.4(12) . . . . ?
N2 C5 C24 C25 -2.3(11) . . . . ?
C6 C5 C24 C25 177.9(7) . . . . ?
C22 C23 C24 C5 -2.5(12) . . . . ?
C22 C23 C24 C25 178.3(8) . . . . ?
C5 C24 C25 C26 2.9(12) . . . . ?
C23 C24 C25 C26 -177.9(8) . . . . ?
C5 C24 C25 C33 179.2(8) . . . . ?
C23 C24 C25 C33 -1.7(12) . . . . ?
C24 C25 C26 C4 -3.3(12) . . . . ?
C33 C25 C26 C4 -179.3(8) . . . . ?
C24 C25 C26 C27 175.4(8) . . . . ?
C33 C25 C26 C27 -0.5(13) . . . . ?
C3 C4 C26 C25 -178.3(9) . . . . ?
N2 C4 C26 C25 3.2(11) . . . . ?
C3 C4 C26 C27 2.9(14) . . . . ?
N2 C4 C26 C27 -175.7(7) . . . . ?
C25 C26 C27 C32 64.7(12) . . . . ?
C4 C26 C27 C32 -116.5(9) . . . . ?
C25 C26 C27 C28 -115.9(10) . . . . ?
C4 C26 C27 C28 62.9(10) . . . . ?
C32 C27 C28 C29 2.0(12) . . . . ?
C26 C27 C28 C29 -177.4(8) . . . . ?
C27 C28 C29 C30 -2.2(14) . . . . ?
C28 C29 C30 C31 2.3(15) . . . . ?
C29 C30 C31 C32 -2.3(15) . . . . ?
C30 C31 C32 C27 2.2(14) . . . . ?
C28 C27 C32 C31 -2.2(13) . . . . ?
C26 C27 C32 C31 177.2(9) . . . . ?
C26 C25 C33 C34 93.2(11) . . . . ?
C24 C25 C33 C34 -82.9(10) . . . . ?
C26 C25 C33 C38 -89.1(11) . . . . ?
C24 C25 C33 C38 94.8(10) . . . . ?
C38 C33 C34 C35 -3.3(13) . . . . ?
C25 C33 C34 C35 174.5(8) . . . . ?
C33 C34 C35 C36 0.8(14) . . . . ?
C34 C35 C36 C37 1.0(16) . . . . ?
C35 C36 C37 C38 -0.3(17) . . . . ?
C36 C37 C38 C33 -2.3(16) . . . . ?
C34 C33 C38 C37 4.1(14) . . . . ?
C25 C33 C38 C37 -173.7(9) . . . . ?
N2 C1 N1 C3 -2.1(9) . . . . ?
C8 C1 N1 C3 -179.8(9) . . . . ?
N2 C1 N1 C2 179.9(8) . . . . ?
C8 C1 N1 C2 2.2(15) . . . . ?
C4 C3 N1 C1 2.9(10) . . . . ?
C4 C3 N1 C2 -178.8(8) . . . . ?
C24 C5 N2 C1 178.9(7) . . . . ?
C6 C5 N2 C1 -1.2(10) . . . . ?
C24 C5 N2 C4 2.4(11) . . . . ?
C6 C5 N2 C4 -177.7(7) . . . . ?
N1 C1 N2 C5 -176.5(6) . . . . ?
C8 C1 N2 C5 1.6(11) . . . . ?
N1 C1 N2 C4 0.5(8) . . . . ?
C8 C1 N2 C4 178.7(7) . . . . ?
C3 C4 N2 C5 178.2(7) . . . . ?
C26 C4 N2 C5 -2.8(11) . . . . ?
C3 C4 N2 C1 1.3(9) . . . . ?
C26 C4 N2 C1 -179.8(7) . . . . ?
F3 C40 S1 O1 -160(5) . . . . ?
F2 C40 S1 O1 35(4) . . . . ?
F1 C40 S1 O1 -64(2) . . . . ?
F3 C40 S1 O3 -24(6) . . . . ?
F2 C40 S1 O3 170(3) . . . . ?
F1 C40 S1 O3 72(3) . . . . ?
F3 C40 S1 O2 86(5) . . . . ?
F2 C40 S1 O2 -80(4) . . . . ?
F1 C40 S1 O2 -178(3) . . . . ?

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
C2 H2C F1 0.96 2.60 3.23(2) 123.7 4_666
C39 H39 O1 0.98 2.12 3.097(17) 174.9 .
C39 H39 O1 0.98 2.12 3.097(17) 174.9 .

_refine_diff_density_max         0.719
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.167

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_shelx_CCDC1
_audit_block_doi                 10.5517/cc141ptp
_database_code_depnum_ccdc_archive 'CCDC 1044322'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acscatal.5b00243 2015
_audit_update_record             
;
2015-09-18 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45 H31 F3 N2 O3 S'
_chemical_formula_weight         736.78

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      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                   10.6172(5)
_cell_length_b                   12.7911(7)
_cell_length_c                   14.6372(7)
_cell_angle_alpha                102.793(4)
_cell_angle_beta                 106.868(3)
_cell_angle_gamma                96.170(4)
_cell_volume                     1823.39(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5978
_cell_measurement_theta_min      2.039
_cell_measurement_theta_max      24.404

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             764
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.149
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25491
_diffrn_reflns_av_unetI/netI     0.0909
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.039
_diffrn_reflns_theta_max         24.404
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.904
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.904
_reflns_number_total             5978
_reflns_number_gt                3184
_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       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_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)+(0.2000P)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     SHELXL
_refine_ls_extinction_coef       0.008(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5978
_refine_ls_number_parameters     488
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1744
_refine_ls_R_factor_gt           0.1189
_refine_ls_wR_factor_ref         0.4055
_refine_ls_wR_factor_gt          0.3443
_refine_ls_goodness_of_fit_ref   1.337
_refine_ls_restrained_S_all      1.387
_refine_ls_shift/su_max          5.152
_refine_ls_shift/su_mean         0.037

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 0.6060(5) 0.2305(4) -0.0242(4) 0.0536(13) Uani 1 1 d . . . . .
C2 C 0.6559(6) 0.2531(4) 0.1397(4) 0.0569(14) Uani 1 1 d . . . . .
C3 C 0.5535(6) 0.3047(4) 0.1109(4) 0.0571(14) Uani 1 1 d . . . . .
H3 H 0.5097 0.3415 0.1510 0.068 Uiso 1 1 calc R U . . .
C4 C 0.5939(5) 0.2015(4) -0.1261(4) 0.0562(14) Uani 1 1 d . . . . .
C5 C 0.5109(6) 0.2497(4) -0.1873(4) 0.0590(15) Uani 1 1 d . . . . .
C6 C 0.4328(5) 0.3236(4) -0.1499(4) 0.0586(14) Uani 1 1 d . . . . .
C7 C 0.3425(6) 0.3728(5) -0.2102(5) 0.0745(17) Uani 1 1 d . . . . .
H7 H 0.3375 0.3634 -0.2761 0.089 Uiso 1 1 calc R U . . .
C8 C 0.2619(7) 0.4346(5) -0.1730(5) 0.0775(18) Uani 1 1 d . . . . .
H8 H 0.2040 0.4678 -0.2135 0.093 Uiso 1 1 calc R U . . .
C9 C 0.2659(6) 0.4481(5) -0.0746(5) 0.0728(17) Uani 1 1 d . . . . .
H9 H 0.2091 0.4886 -0.0507 0.087 Uiso 1 1 calc R U . . .
C10 C 0.3516(6) 0.4028(5) -0.0143(4) 0.0679(16) Uani 1 1 d . . . . .
H10 H 0.3549 0.4129 0.0513 0.081 Uiso 1 1 calc R U . . .
C11 C 0.4354(6) 0.3407(4) -0.0508(4) 0.0568(14) Uani 1 1 d . . . . .
C12 C 0.8170(5) 0.1669(5) 0.0671(4) 0.0593(15) Uani 1 1 d . . . . .
H12A H 0.8895 0.2229 0.1147 0.071 Uiso 1 1 calc R U . . .
H12B H 0.8333 0.1531 0.0040 0.071 Uiso 1 1 calc R U . . .
C13 C 0.8146(5) 0.0654(5) 0.1003(4) 0.0615(15) Uani 1 1 d . . . . .
C14 C 0.8041(5) 0.0676(5) 0.1948(4) 0.0569(14) Uani 1 1 d . . . . .
C15 C 0.7926(5) 0.1672(4) 0.2644(4) 0.0553(14) Uani 1 1 d . . . . .
C16 C 0.7288(5) 0.2479(4) 0.2407(4) 0.0565(14) Uani 1 1 d . . . . .
C17 C 0.8317(6) -0.0312(5) 0.0422(4) 0.0734(18) Uani 1 1 d . . . . .
H17 H 0.8400 -0.0322 -0.0195 0.088 Uiso 1 1 calc R U . . .
C18 C 0.8366(7) -0.1236(6) 0.0733(5) 0.087(2) Uani 1 1 d . . . . .
H18 H 0.8497 -0.1865 0.0338 0.105 Uiso 1 1 calc R U . . .
C19 C 0.8221(7) -0.1236(5) 0.1632(5) 0.0817(19) Uani 1 1 d . . . . .
H19 H 0.8213 -0.1877 0.1833 0.098 Uiso 1 1 calc R U . . .
C20 C 0.8087(6) -0.0289(5) 0.2246(4) 0.0664(16) Uani 1 1 d . . . . .
H20 H 0.8026 -0.0296 0.2866 0.080 Uiso 1 1 calc R U . . .
C21 C 0.6590(6) 0.1119(5) -0.1654(4) 0.0622(15) Uani 1 1 d . . . . .
C22 C 0.6083(7) 0.0050(5) -0.1672(5) 0.0755(18) Uani 1 1 d . . . . .
H22 H 0.5387 -0.0078 -0.1422 0.091 Uiso 1 1 calc R U . . .
C23 C 0.6630(9) -0.0823(7) -0.2068(5) 0.093(2) Uani 1 1 d . . . . .
H23 H 0.6297 -0.1530 -0.2079 0.112 Uiso 1 1 calc R U . . .
C24 C 0.7619(11) -0.0641(9) -0.2427(6) 0.111(3) Uani 1 1 d . . . . .
H24 H 0.7972 -0.1228 -0.2686 0.133 Uiso 1 1 calc R U . . .
C25 C 0.8144(8) 0.0401(9) -0.2428(5) 0.100(3) Uani 1 1 d . . . . .
H25 H 0.8849 0.0509 -0.2673 0.120 Uiso 1 1 calc R U . . .
C26 C 0.7594(7) 0.1298(7) -0.2051(5) 0.084(2) Uani 1 1 d . . . . .
H26 H 0.7908 0.1996 -0.2073 0.100 Uiso 1 1 calc R U . . .
C27 C 0.4983(6) 0.2263(5) -0.2944(4) 0.0616(15) Uani 1 1 d . . . . .
C28 C 0.4294(7) 0.1251(6) -0.3597(4) 0.0777(18) Uani 1 1 d . . . . .
H28 H 0.3952 0.0711 -0.3353 0.093 Uiso 1 1 calc R U . . .
C29 C 0.4120(7) 0.1047(7) -0.4587(5) 0.086(2) Uani 1 1 d . . . . .
H29 H 0.3625 0.0385 -0.5016 0.103 Uiso 1 1 calc R U . . .
C30 C 0.4672(8) 0.1817(8) -0.4948(5) 0.097(2) Uani 1 1 d . . . . .
H30 H 0.4587 0.1667 -0.5617 0.117 Uiso 1 1 calc R U . . .
C31 C 0.5356(9) 0.2819(8) -0.4311(6) 0.101(2) Uani 1 1 d . . . . .
H31 H 0.5723 0.3346 -0.4555 0.121 Uiso 1 1 calc R U . . .
C32 C 0.5496(7) 0.3042(6) -0.3318(5) 0.0800(19) Uani 1 1 d . . . . .
H32 H 0.5940 0.3723 -0.2899 0.096 Uiso 1 1 calc R U . . .
C33 C 0.8591(6) 0.1729(4) 0.3714(4) 0.0581(14) Uani 1 1 d . . . . .
C34 C 0.9960(6) 0.1765(5) 0.4073(4) 0.0725(17) Uani 1 1 d . . . . .
H34 H 1.0470 0.1771 0.3653 0.087 Uiso 1 1 calc R U . . .
C35 C 1.0567(8) 0.1791(6) 0.5044(6) 0.095(2) Uani 1 1 d . . . . .
H35 H 1.1483 0.1804 0.5280 0.114 Uiso 1 1 calc R U . . .
C36 C 0.9804(11) 0.1796(7) 0.5678(6) 0.107(3) Uani 1 1 d . . . . .
H36 H 1.0214 0.1807 0.6335 0.128 Uiso 1 1 calc R U . . .
C37 C 0.8495(9) 0.1787(7) 0.5346(5) 0.098(2) Uani 1 1 d . . . . .
H37 H 0.7997 0.1816 0.5777 0.118 Uiso 1 1 calc R U . . .
C38 C 0.7875(7) 0.1734(5) 0.4361(4) 0.0749(17) Uani 1 1 d . . . . .
H38 H 0.6955 0.1701 0.4131 0.090 Uiso 1 1 calc R U . . .
C39 C 0.7298(6) 0.3474(5) 0.3181(4) 0.0593(15) Uani 1 1 d . . . . .
C40 C 0.6154(7) 0.3665(5) 0.3400(4) 0.0723(17) Uani 1 1 d . . . . .
H40 H 0.5365 0.3155 0.3086 0.087 Uiso 1 1 calc R U . . .
C41 C 0.6170(9) 0.4613(6) 0.4084(5) 0.083(2) Uani 1 1 d . . . . .
H41 H 0.5397 0.4727 0.4239 0.100 Uiso 1 1 calc R U . . .
C42 C 0.7320(10) 0.5387(6) 0.4535(5) 0.092(2) Uani 1 1 d . . . . .
H42 H 0.7326 0.6034 0.4977 0.110 Uiso 1 1 calc R U . . .
C43 C 0.8471(9) 0.5183(6) 0.4319(5) 0.098(2) Uani 1 1 d . . . . .
H43 H 0.9265 0.5685 0.4643 0.117 Uiso 1 1 calc R U . . .
C44 C 0.8456(7) 0.4253(5) 0.3634(4) 0.0722(17) Uani 1 1 d . . . . .
H44 H 0.9227 0.4146 0.3473 0.087 Uiso 1 1 calc R U . . .
C45 C 1.1162(10) 0.4790(16) 0.1974(13) 0.51(3) Uani 1 1 d D . . . .
N1 N 0.6875(4) 0.2063(4) 0.0564(3) 0.0540(12) Uani 1 1 d . . . . .
N2 N 0.5253(4) 0.2929(4) 0.0098(3) 0.0566(12) Uani 1 1 d . . . . .
O1 O 1.1144(14) 0.3049(12) 0.1012(9) 0.421(16) Uani 1 1 d D . . . .
O2 O 1.1299(10) 0.3134(9) 0.2628(8) 0.218(5) Uani 1 1 d D . . . .
O3 O 1.3175(8) 0.3833(10) 0.2101(8) 0.237(6) Uani 1 1 d D . . . .
F1 F 0.9858(9) 0.4518(10) 0.1692(9) 0.272(5) Uani 1 1 d D . . . .
F2 F 1.183(2) 0.514(2) 0.2964(11) 0.74(4) Uani 1 1 d D . . . .
F3 F 1.1617(10) 0.5319(7) 0.1421(7) 0.228(4) Uani 1 1 d D . . . .
S1 S 1.1920(2) 0.36689(19) 0.21059(19) 0.1089(9) Uani 1 1 d 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 N2 1.356(7) . ?
C1 N1 1.366(6) . ?
C1 C4 1.418(7) . ?
C2 C3 1.344(8) . ?
C2 N1 1.384(6) . ?
C2 C16 1.477(7) . ?
C3 N2 1.391(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(8) . ?
C4 C21 1.493(8) . ?
C5 C6 1.444(8) . ?
C5 C27 1.492(7) . ?
C6 C7 1.407(8) . ?
C6 C11 1.410(7) . ?
C7 C8 1.371(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.399(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.347(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.396(8) . ?
C10 H10 0.9300 . ?
C11 N2 1.395(7) . ?
C12 N1 1.492(7) . ?
C12 C13 1.485(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C17 1.399(8) . ?
C13 C14 1.414(8) . ?
C14 C20 1.398(8) . ?
C14 C15 1.486(8) . ?
C15 C16 1.348(8) . ?
C15 C33 1.501(7) . ?
C16 C39 1.502(8) . ?
C17 C18 1.358(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.368(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.388(9) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.376(8) . ?
C21 C22 1.407(8) . ?
C22 C23 1.403(9) . ?
C22 H22 0.9300 . ?
C23 C24 1.325(12) . ?
C23 H23 0.9300 . ?
C24 C25 1.388(12) . ?
C24 H24 0.9300 . ?
C25 C26 1.418(11) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C32 1.374(8) . ?
C27 C28 1.403(8) . ?
C28 C29 1.367(9) . ?
C28 H28 0.9300 . ?
C29 C30 1.371(11) . ?
C29 H29 0.9300 . ?
C30 C31 1.385(11) . ?
C30 H30 0.9300 . ?
C31 C32 1.378(9) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 C38 1.375(8) . ?
C33 C34 1.387(8) . ?
C34 C35 1.372(9) . ?
C34 H34 0.9300 . ?
C35 C36 1.396(11) . ?
C35 H35 0.9300 . ?
C36 C37 1.330(11) . ?
C36 H36 0.9300 . ?
C37 C38 1.384(9) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 C44 1.384(8) . ?
C39 C40 1.375(8) . ?
C40 C41 1.387(9) . ?
C40 H40 0.9300 . ?
C41 C42 1.375(11) . ?
C41 H41 0.9300 . ?
C42 C43 1.384(11) . ?
C42 H42 0.9300 . ?
C43 C44 1.371(9) . ?
C43 H43 0.9300 . ?
C44 H44 0.9300 . ?
C45 F1 1.307(11) . ?
C45 F3 1.321(11) . ?
C45 F2 1.361(15) . ?
C45 S1 1.739(17) . ?
O1 S1 1.550(10) . ?
O2 S1 1.384(6) . ?
O3 S1 1.329(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
N2 C1 N1 106.0(4) . . ?
N2 C1 C4 121.3(5) . . ?
N1 C1 C4 132.7(5) . . ?
C3 C2 N1 107.6(5) . . ?
C3 C2 C16 128.4(5) . . ?
N1 C2 C16 124.0(5) . . ?
C2 C3 N2 107.2(5) . . ?
C2 C3 H3 126.4 . . ?
N2 C3 H3 126.4 . . ?
C5 C4 C1 118.0(5) . . ?
C5 C4 C21 121.6(5) . . ?
C1 C4 C21 120.0(5) . . ?
C4 C5 C6 120.7(5) . . ?
C4 C5 C27 120.6(5) . . ?
C6 C5 C27 118.7(5) . . ?
C7 C6 C11 116.9(5) . . ?
C7 C6 C5 123.1(5) . . ?
C11 C6 C5 119.7(5) . . ?
C8 C7 C6 120.8(6) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.5(6) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 120.5(6) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.7(5) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 N2 121.0(5) . . ?
C10 C11 C6 121.6(5) . . ?
N2 C11 C6 117.4(5) . . ?
N1 C12 C13 110.9(4) . . ?
N1 C12 H12A 109.4 . . ?
C13 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.0 . . ?
C17 C13 C14 119.2(6) . . ?
C17 C13 C12 120.8(5) . . ?
C14 C13 C12 119.9(5) . . ?
C20 C14 C13 117.7(5) . . ?
C20 C14 C15 118.8(5) . . ?
C13 C14 C15 123.4(5) . . ?
C16 C15 C14 127.0(5) . . ?
C16 C15 C33 119.4(5) . . ?
C14 C15 C33 113.6(5) . . ?
C15 C16 C2 126.0(5) . . ?
C15 C16 C39 121.9(5) . . ?
C2 C16 C39 112.1(5) . . ?
C18 C17 C13 121.9(6) . . ?
C18 C17 H17 119.1 . . ?
C13 C17 H17 119.1 . . ?
C17 C18 C19 119.5(6) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C18 120.6(7) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C14 121.0(6) . . ?
C19 C20 H20 119.5 . . ?
C14 C20 H20 119.5 . . ?
C26 C21 C22 119.7(6) . . ?
C26 C21 C4 122.4(6) . . ?
C22 C21 C4 117.8(5) . . ?
C23 C22 C21 119.9(7) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C24 C23 C22 120.1(8) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 121.9(8) . . ?
C23 C24 H24 119.0 . . ?
C25 C24 H24 119.0 . . ?
C26 C25 C24 119.4(7) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C21 C26 C25 119.0(8) . . ?
C21 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
C32 C27 C28 118.6(5) . . ?
C32 C27 C5 121.0(5) . . ?
C28 C27 C5 120.4(5) . . ?
C29 C28 C27 120.8(7) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C28 C29 C30 120.2(7) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C31 C30 C29 119.5(7) . . ?
C31 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C30 C31 C32 120.5(7) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.7 . . ?
C27 C32 C31 120.3(7) . . ?
C27 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C38 C33 C34 118.1(5) . . ?
C38 C33 C15 121.8(5) . . ?
C34 C33 C15 120.1(5) . . ?
C35 C34 C33 120.3(6) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C34 C35 C36 119.8(7) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
C37 C36 C35 120.4(7) . . ?
C37 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
C36 C37 C38 119.9(7) . . ?
C36 C37 H37 120.0 . . ?
C38 C37 H37 120.0 . . ?
C33 C38 C37 121.4(7) . . ?
C33 C38 H38 119.3 . . ?
C37 C38 H38 119.3 . . ?
C44 C39 C40 119.2(6) . . ?
C44 C39 C16 119.4(5) . . ?
C40 C39 C16 121.3(5) . . ?
C39 C40 C41 120.4(7) . . ?
C39 C40 H40 119.8 . . ?
C41 C40 H40 119.8 . . ?
C42 C41 C40 120.4(7) . . ?
C42 C41 H41 119.8 . . ?
C40 C41 H41 119.8 . . ?
C43 C42 C41 118.8(7) . . ?
C43 C42 H42 120.6 . . ?
C41 C42 H42 120.6 . . ?
C42 C43 C44 121.0(7) . . ?
C42 C43 H43 119.5 . . ?
C44 C43 H43 119.5 . . ?
C39 C44 C43 120.1(7) . . ?
C39 C44 H44 119.9 . . ?
C43 C44 H44 119.9 . . ?
F1 C45 F3 114.6(10) . . ?
F1 C45 F2 117.8(14) . . ?
F3 C45 F2 115.3(14) . . ?
F1 C45 S1 111.2(12) . . ?
F3 C45 S1 111.6(11) . . ?
F2 C45 S1 81.8(16) . . ?
C1 N1 C2 109.6(4) . . ?
C1 N1 C12 128.0(4) . . ?
C2 N1 C12 120.1(4) . . ?
C1 N2 C3 109.7(4) . . ?
C1 N2 C11 122.2(4) . . ?
C3 N2 C11 128.0(5) . . ?
O3 S1 O2 132.7(6) . . ?
O3 S1 O1 102.1(6) . . ?
O2 S1 O1 103.1(6) . . ?
O3 S1 C45 112.2(6) . . ?
O2 S1 C45 106.6(6) . . ?
O1 S1 C45 91.1(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 -2.1(6) . . . . ?
C16 C2 C3 N2 175.6(5) . . . . ?
N2 C1 C4 C5 8.6(8) . . . . ?
N1 C1 C4 C5 -172.9(5) . . . . ?
N2 C1 C4 C21 -164.9(5) . . . . ?
N1 C1 C4 C21 13.6(9) . . . . ?
C1 C4 C5 C6 -3.2(8) . . . . ?
C21 C4 C5 C6 170.2(5) . . . . ?
C1 C4 C5 C27 177.3(5) . . . . ?
C21 C4 C5 C27 -9.3(8) . . . . ?
C4 C5 C6 C7 -177.9(6) . . . . ?
C27 C5 C6 C7 1.6(8) . . . . ?
C4 C5 C6 C11 -4.2(8) . . . . ?
C27 C5 C6 C11 175.3(5) . . . . ?
C11 C6 C7 C8 0.2(9) . . . . ?
C5 C6 C7 C8 174.0(6) . . . . ?
C6 C7 C8 C9 -1.3(10) . . . . ?
C7 C8 C9 C10 1.7(10) . . . . ?
C8 C9 C10 C11 -1.0(10) . . . . ?
C9 C10 C11 N2 179.9(5) . . . . ?
C9 C10 C11 C6 -0.1(9) . . . . ?
C7 C6 C11 C10 0.5(8) . . . . ?
C5 C6 C11 C10 -173.6(5) . . . . ?
C7 C6 C11 N2 -179.5(5) . . . . ?
C5 C6 C11 N2 6.4(8) . . . . ?
N1 C12 C13 C17 119.7(5) . . . . ?
N1 C12 C13 C14 -64.7(6) . . . . ?
C17 C13 C14 C20 -1.3(8) . . . . ?
C12 C13 C14 C20 -177.0(5) . . . . ?
C17 C13 C14 C15 176.8(5) . . . . ?
C12 C13 C14 C15 1.1(8) . . . . ?
C20 C14 C15 C16 -147.3(6) . . . . ?
C13 C14 C15 C16 34.5(8) . . . . ?
C20 C14 C15 C33 31.5(7) . . . . ?
C13 C14 C15 C33 -146.6(5) . . . . ?
C14 C15 C16 C2 0.5(9) . . . . ?
C33 C15 C16 C2 -178.3(5) . . . . ?
C14 C15 C16 C39 -177.1(5) . . . . ?
C33 C15 C16 C39 4.1(8) . . . . ?
C3 C2 C16 C15 153.3(6) . . . . ?
N1 C2 C16 C15 -29.4(9) . . . . ?
C3 C2 C16 C39 -28.9(8) . . . . ?
N1 C2 C16 C39 148.5(5) . . . . ?
C14 C13 C17 C18 1.0(9) . . . . ?
C12 C13 C17 C18 176.7(6) . . . . ?
C13 C17 C18 C19 1.2(10) . . . . ?
C17 C18 C19 C20 -3.0(10) . . . . ?
C18 C19 C20 C14 2.6(10) . . . . ?
C13 C14 C20 C19 -0.4(8) . . . . ?
C15 C14 C20 C19 -178.7(5) . . . . ?
C5 C4 C21 C26 70.3(8) . . . . ?
C1 C4 C21 C26 -116.4(6) . . . . ?
C5 C4 C21 C22 -105.4(6) . . . . ?
C1 C4 C21 C22 67.9(7) . . . . ?
C26 C21 C22 C23 1.8(9) . . . . ?
C4 C21 C22 C23 177.7(5) . . . . ?
C21 C22 C23 C24 -0.2(11) . . . . ?
C22 C23 C24 C25 -0.1(12) . . . . ?
C23 C24 C25 C26 -1.2(12) . . . . ?
C22 C21 C26 C25 -3.1(9) . . . . ?
C4 C21 C26 C25 -178.8(6) . . . . ?
C24 C25 C26 C21 2.8(11) . . . . ?
C4 C5 C27 C32 -109.7(7) . . . . ?
C6 C5 C27 C32 70.8(8) . . . . ?
C4 C5 C27 C28 72.6(8) . . . . ?
C6 C5 C27 C28 -106.9(7) . . . . ?
C32 C27 C28 C29 -0.9(10) . . . . ?
C5 C27 C28 C29 176.9(6) . . . . ?
C27 C28 C29 C30 3.0(11) . . . . ?
C28 C29 C30 C31 -2.9(11) . . . . ?
C29 C30 C31 C32 0.7(11) . . . . ?
C28 C27 C32 C31 -1.3(10) . . . . ?
C5 C27 C32 C31 -179.1(6) . . . . ?
C30 C31 C32 C27 1.4(11) . . . . ?
C16 C15 C33 C38 61.7(8) . . . . ?
C14 C15 C33 C38 -117.2(6) . . . . ?
C16 C15 C33 C34 -119.0(6) . . . . ?
C14 C15 C33 C34 62.0(7) . . . . ?
C38 C33 C34 C35 0.8(9) . . . . ?
C15 C33 C34 C35 -178.5(6) . . . . ?
C33 C34 C35 C36 -0.9(11) . . . . ?
C34 C35 C36 C37 -0.6(12) . . . . ?
C35 C36 C37 C38 2.2(13) . . . . ?
C34 C33 C38 C37 0.8(10) . . . . ?
C15 C33 C38 C37 -180.0(6) . . . . ?
C36 C37 C38 C33 -2.3(12) . . . . ?
C15 C16 C39 C44 73.1(7) . . . . ?
C2 C16 C39 C44 -104.8(6) . . . . ?
C15 C16 C39 C40 -111.6(6) . . . . ?
C2 C16 C39 C40 70.5(7) . . . . ?
C44 C39 C40 C41 -1.7(9) . . . . ?
C16 C39 C40 C41 -177.0(5) . . . . ?
C39 C40 C41 C42 1.6(10) . . . . ?
C40 C41 C42 C43 -2.2(10) . . . . ?
C41 C42 C43 C44 3.0(11) . . . . ?
C40 C39 C44 C43 2.5(9) . . . . ?
C16 C39 C44 C43 177.9(6) . . . . ?
C42 C43 C44 C39 -3.2(10) . . . . ?
N2 C1 N1 C2 0.5(5) . . . . ?
C4 C1 N1 C2 -178.2(6) . . . . ?
N2 C1 N1 C12 -161.8(5) . . . . ?
C4 C1 N1 C12 19.5(9) . . . . ?
C3 C2 N1 C1 1.0(6) . . . . ?
C16 C2 N1 C1 -176.8(5) . . . . ?
C3 C2 N1 C12 165.0(5) . . . . ?
C16 C2 N1 C12 -12.9(7) . . . . ?
C13 C12 N1 C1 -126.5(5) . . . . ?
C13 C12 N1 C2 72.8(6) . . . . ?
N1 C1 N2 C3 -1.8(5) . . . . ?
C4 C1 N2 C3 177.1(5) . . . . ?
N1 C1 N2 C11 174.7(5) . . . . ?
C4 C1 N2 C11 -6.4(8) . . . . ?
C2 C3 N2 C1 2.5(6) . . . . ?
C2 C3 N2 C11 -173.7(5) . . . . ?
C10 C11 N2 C1 178.8(5) . . . . ?
C6 C11 N2 C1 -1.2(8) . . . . ?
C10 C11 N2 C3 -5.4(8) . . . . ?
C6 C11 N2 C3 174.6(5) . . . . ?
F1 C45 S1 O3 161.4(10) . . . . ?
F3 C45 S1 O3 32.1(14) . . . . ?
F2 C45 S1 O3 -82.0(11) . . . . ?
F1 C45 S1 O2 -46.2(13) . . . . ?
F3 C45 S1 O2 -175.5(10) . . . . ?
F2 C45 S1 O2 70.5(9) . . . . ?
F1 C45 S1 O1 57.8(11) . . . . ?
F3 C45 S1 O1 -71.5(11) . . . . ?
F2 C45 S1 O1 174.5(9) . . . . ?

_refine_diff_density_max         1.204
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.083

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_shelx_CCDC2
_audit_block_doi                 10.5517/cc141psn
_database_code_depnum_ccdc_archive 'CCDC 1044321'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acscatal.5b00243 2015
_audit_update_record             
;
2015-09-18 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H27 F3 N2 O4 S'
_chemical_formula_weight         580.60

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      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                   9.4555(15)
_cell_length_b                   12.671(2)
_cell_length_c                   13.141(2)
_cell_angle_alpha                89.372(7)
_cell_angle_beta                 83.024(8)
_cell_angle_gamma                70.301(7)
_cell_volume                     1470.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4778
_cell_measurement_theta_min      2.306
_cell_measurement_theta_max      24.406

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             604
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.167
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37491
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_av_R_equivalents  0.1210
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.306
_diffrn_reflns_theta_max         24.406
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.898
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.898
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.898
_reflns_number_total             4778
_reflns_number_gt                2254
_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       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-3
_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)+(0.2000P)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         4778
_refine_ls_number_parameters     370
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.2602
_refine_ls_R_factor_gt           0.1690
_refine_ls_wR_factor_ref         0.4905
_refine_ls_wR_factor_gt          0.4462
_refine_ls_goodness_of_fit_ref   1.644
_refine_ls_restrained_S_all      1.699
_refine_ls_shift/su_max          1.535
_refine_ls_shift/su_mean         0.008

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 0.3120(8) 0.2029(6) 0.3731(6) 0.0581(19) Uani 1 1 d . . . . .
C2 C 0.2543(13) 0.4127(7) 0.3568(8) 0.107(3) Uani 1 1 d . . . . .
H2A H 0.3142 0.3919 0.2911 0.160 Uiso 1 1 calc R U . . .
H2B H 0.1553 0.4634 0.3478 0.160 Uiso 1 1 calc R U . . .
H2C H 0.3022 0.4487 0.3986 0.160 Uiso 1 1 calc R U . . .
C3 C 0.1634(9) 0.3147(6) 0.5000(6) 0.067(2) Uani 1 1 d . . . . .
H3 H 0.1061 0.3793 0.5387 0.080 Uiso 1 1 calc R U . . .
C4 C 0.1814(8) 0.2091(6) 0.5290(6) 0.0599(19) Uani 1 1 d . . . . .
C5 C 0.1239(8) 0.1582(6) 0.6151(5) 0.0593(19) Uani 1 1 d . . . . .
C6 C 0.1719(8) 0.0415(6) 0.6183(5) 0.0595(19) Uani 1 1 d . . . . .
C7 C 0.2798(8) -0.0253(5) 0.5363(5) 0.0539(18) Uani 1 1 d . . . . .
C8 C 0.3288(8) 0.0252(5) 0.4490(5) 0.0525(18) Uani 1 1 d . . . . .
C9 C 0.4251(8) -0.0299(6) 0.3648(6) 0.0583(19) Uani 1 1 d . . . . .
C10 C 0.4549(8) 0.0346(6) 0.2773(6) 0.064(2) Uani 1 1 d . . . . .
C11 C 0.3964(8) 0.1504(6) 0.2818(6) 0.062(2) Uani 1 1 d . . . . .
C12 C 0.4067(10) 0.2206(6) 0.1879(6) 0.073(2) Uani 1 1 d . . . . .
C13 C 0.2858(11) 0.2590(8) 0.1338(7) 0.090(3) Uani 1 1 d . . . . .
H13 H 0.2002 0.2395 0.1535 0.107 Uiso 1 1 calc R U . . .
C14 C 0.2878(13) 0.3256(8) 0.0511(8) 0.105(3) Uani 1 1 d . . . . .
H14 H 0.2022 0.3554 0.0178 0.126 Uiso 1 1 calc R U . . .
C15 C 0.4197(16) 0.3479(8) 0.0177(7) 0.105(3) Uani 1 1 d . . . . .
H15 H 0.4250 0.3895 -0.0405 0.126 Uiso 1 1 calc R U . . .
C16 C 0.5403(14) 0.3084(9) 0.0705(8) 0.105(3) Uani 1 1 d . . . . .
H16 H 0.6277 0.3253 0.0498 0.126 Uiso 1 1 calc R U . . .
C17 C 0.5347(11) 0.2428(7) 0.1557(7) 0.088(3) Uani 1 1 d . . . . .
H17 H 0.6191 0.2142 0.1903 0.106 Uiso 1 1 calc R U . . .
C18 C 0.5402(10) -0.0262(7) 0.1807(7) 0.092(3) Uani 1 1 d . . . . .
H18A H 0.6243 -0.0907 0.1964 0.110 Uiso 1 1 calc R U . . .
H18B H 0.5809 0.0228 0.1386 0.110 Uiso 1 1 calc R U . . .
C19 C 0.4318(14) -0.0660(9) 0.1199(8) 0.122(4) Uani 1 1 d . . . . .
H19A H 0.4874 -0.1052 0.0576 0.183 Uiso 1 1 calc R U . . .
H19B H 0.3927 -0.1152 0.1615 0.183 Uiso 1 1 calc R U . . .
H19C H 0.3494 -0.0019 0.1037 0.183 Uiso 1 1 calc R U . . .
C20 C 0.4807(8) -0.1483(6) 0.3678(6) 0.067(2) Uani 1 1 d . . . . .
H20 H 0.5456 -0.1900 0.3125 0.081 Uiso 1 1 calc R U . . .
C21 C 0.4407(9) -0.2013(6) 0.4500(7) 0.068(2) Uani 1 1 d . . . . .
H21 H 0.4811 -0.2791 0.4512 0.082 Uiso 1 1 calc R U . . .
C22 C 0.3392(9) -0.1417(6) 0.5339(6) 0.069(2) Uani 1 1 d . . . . .
H22 H 0.3115 -0.1808 0.5886 0.083 Uiso 1 1 calc R U . . .
C23 C 0.1075(9) -0.0148(6) 0.7032(6) 0.071(2) Uani 1 1 d . . . . .
H23A H 0.0688 0.0361 0.7626 0.086 Uiso 1 1 calc R U . . .
H23B H 0.1869 -0.0804 0.7227 0.086 Uiso 1 1 calc R U . . .
C24 C -0.0196(11) -0.0499(8) 0.6702(8) 0.102(3) Uani 1 1 d . . . . .
H24A H -0.0592 -0.0858 0.7258 0.152 Uiso 1 1 calc R U . . .
H24B H -0.0988 0.0152 0.6520 0.152 Uiso 1 1 calc R U . . .
H24C H 0.0190 -0.1012 0.6121 0.152 Uiso 1 1 calc R U . . .
C25 C 0.0038(8) 0.2331(6) 0.6905(6) 0.0601(19) Uani 1 1 d . . . . .
C26 C 0.0340(12) 0.2759(9) 0.7752(9) 0.119(4) Uani 1 1 d . . . . .
H26 H 0.1340 0.2608 0.7864 0.143 Uiso 1 1 calc R U . . .
C27 C -0.0841(17) 0.3434(10) 0.8473(9) 0.134(5) Uani 1 1 d . . . . .
H27 H -0.0610 0.3658 0.9085 0.160 Uiso 1 1 calc R U . . .
C28 C -0.2248(16) 0.3749(8) 0.8298(10) 0.107(4) Uani 1 1 d . . . . .
H28 H -0.3012 0.4217 0.8769 0.129 Uiso 1 1 calc R U . . .
C29 C -0.2592(12) 0.3381(9) 0.7406(13) 0.130(4) Uani 1 1 d . . . . .
H29 H -0.3590 0.3611 0.7266 0.156 Uiso 1 1 calc R U . . .
C30 C -0.1454(11) 0.2669(9) 0.6719(9) 0.112(3) Uani 1 1 d . . . . .
H30 H -0.1696 0.2415 0.6125 0.134 Uiso 1 1 calc R U . . .
C31 C 0.2516(17) 0.4966(13) 0.7702(10) 0.37(2) Uani 1 1 d D U . . .
N1 N 0.2407(8) 0.3125(5) 0.4068(5) 0.0728(19) Uani 1 1 d . . . . .
N2 N 0.2729(6) 0.1418(5) 0.4499(4) 0.0575(16) Uani 1 1 d . . . . .
O1 O 0.138(2) 0.5638(13) 0.6022(13) 0.347(13) Uani 1 1 d D . . . .
O2 O 0.353(2) 0.6025(17) 0.6251(14) 0.343(11) Uani 1 1 d D . . . .
O3 O 0.139(3) 0.6940(11) 0.710(2) 0.78(5) Uani 1 1 d D . . . .
O4 O 0.0530(16) 0.0830(10) 0.0126(7) 0.216(5) Uani 1 1 d . . . . .
F1 F 0.337(3) 0.5262(14) 0.8147(17) 0.477(19) Uani 1 1 d D . . . .
F2 F 0.303(2) 0.4068(11) 0.727(2) 0.81(5) Uani 1 1 d D . . . .
F3 F 0.119(2) 0.5273(19) 0.8112(18) 0.424(13) Uani 1 1 d D U . . .
S1 S 0.2273(9) 0.5808(5) 0.6621(5) 0.233(3) Uani 1 1 d D 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
C1 N2 1.356(9) . ?
C1 N1 1.376(9) . ?
C1 C11 1.394(10) . ?
C2 N1 1.459(10) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 N1 1.344(9) . ?
C3 C4 1.347(9) . ?
C3 H3 0.9300 . ?
C4 N2 1.363(9) . ?
C4 C5 1.437(10) . ?
C5 C6 1.394(9) . ?
C5 C25 1.481(10) . ?
C6 C7 1.446(10) . ?
C6 C23 1.495(10) . ?
C7 C22 1.388(9) . ?
C7 C8 1.413(10) . ?
C8 C9 1.373(10) . ?
C8 N2 1.391(8) . ?
C9 C20 1.414(10) . ?
C9 C10 1.458(10) . ?
C10 C11 1.382(9) . ?
C10 C18 1.486(10) . ?
C11 C12 1.526(10) . ?
C12 C17 1.351(11) . ?
C12 C13 1.365(11) . ?
C13 C14 1.371(13) . ?
C13 H13 0.9300 . ?
C14 C15 1.388(13) . ?
C14 H14 0.9300 . ?
C15 C16 1.354(14) . ?
C15 H15 0.9300 . ?
C16 C17 1.393(12) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.581(13) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.348(10) . ?
C20 H20 0.9300 . ?
C21 C22 1.408(11) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.524(10) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.345(11) . ?
C25 C30 1.381(12) . ?
C26 C27 1.412(15) . ?
C26 H26 0.9300 . ?
C27 C28 1.302(15) . ?
C27 H27 0.9300 . ?
C28 C29 1.380(16) . ?
C28 H28 0.9300 . ?
C29 C30 1.383(15) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 F2 1.198(16) . ?
C31 F1 1.210(15) . ?
C31 F3 1.232(16) . ?
C31 S1 1.758(10) . ?
O1 S1 1.292(10) . ?
O2 S1 1.341(11) . ?
O3 S1 1.495(15) . ?

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
N2 C1 N1 104.5(6) . . ?
N2 C1 C11 120.6(6) . . ?
N1 C1 C11 134.7(7) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 109.7(7) . . ?
N1 C3 H3 125.2 . . ?
C4 C3 H3 125.2 . . ?
C3 C4 N2 105.3(6) . . ?
C3 C4 C5 135.8(7) . . ?
N2 C4 C5 118.8(6) . . ?
C6 C5 C4 118.9(7) . . ?
C6 C5 C25 123.3(6) . . ?
C4 C5 C25 117.5(6) . . ?
C5 C6 C7 119.6(7) . . ?
C5 C6 C23 120.5(7) . . ?
C7 C6 C23 119.8(6) . . ?
C22 C7 C8 114.7(7) . . ?
C22 C7 C6 124.2(7) . . ?
C8 C7 C6 121.1(6) . . ?
C9 C8 N2 118.0(6) . . ?
C9 C8 C7 126.1(6) . . ?
N2 C8 C7 116.0(6) . . ?
C8 C9 C20 116.0(7) . . ?
C8 C9 C10 119.2(6) . . ?
C20 C9 C10 124.7(7) . . ?
C11 C10 C9 120.5(6) . . ?
C11 C10 C18 120.4(7) . . ?
C9 C10 C18 119.0(7) . . ?
C10 C11 C1 118.0(7) . . ?
C10 C11 C12 122.3(7) . . ?
C1 C11 C12 119.4(7) . . ?
C17 C12 C13 119.4(8) . . ?
C17 C12 C11 121.2(7) . . ?
C13 C12 C11 119.3(8) . . ?
C12 C13 C14 121.4(9) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C15 119.0(9) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C16 C15 C14 119.4(9) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.5(10) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C12 C17 C16 120.0(9) . . ?
C12 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C10 C18 C19 109.8(7) . . ?
C10 C18 H18A 109.7 . . ?
C19 C18 H18A 109.7 . . ?
C10 C18 H18B 109.7 . . ?
C19 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
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 . . ?
C21 C20 C9 120.7(7) . . ?
C21 C20 H20 119.7 . . ?
C9 C20 H20 119.7 . . ?
C20 C21 C22 121.5(7) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C7 C22 C21 121.0(7) . . ?
C7 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C6 C23 C24 110.9(6) . . ?
C6 C23 H23A 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C6 C23 H23B 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 108.1 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C30 117.3(8) . . ?
C26 C25 C5 122.7(7) . . ?
C30 C25 C5 119.9(8) . . ?
C25 C26 C27 120.9(10) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
C28 C27 C26 121.4(11) . . ?
C28 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
C27 C28 C29 119.1(10) . . ?
C27 C28 H28 120.5 . . ?
C29 C28 H28 120.5 . . ?
C28 C29 C30 120.1(11) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C25 C30 C29 120.9(11) . . ?
C25 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
F2 C31 F1 116.7(14) . . ?
F2 C31 F3 118.5(14) . . ?
F1 C31 F3 115.3(14) . . ?
F2 C31 S1 98.3(14) . . ?
F1 C31 S1 103.8(11) . . ?
F3 C31 S1 99.1(12) . . ?
C3 N1 C1 109.1(6) . . ?
C3 N1 C2 123.4(7) . . ?
C1 N1 C2 127.2(7) . . ?
C1 N2 C4 111.5(6) . . ?
C1 N2 C8 123.1(6) . . ?
C4 N2 C8 125.3(6) . . ?
O1 S1 O2 121.7(13) . . ?
O1 S1 O3 103.5(11) . . ?
O2 S1 O3 97.6(9) . . ?
O1 S1 C31 114.9(8) . . ?
O2 S1 C31 112.9(9) . . ?
O3 S1 C31 101.5(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C3 C4 N2 0.0(8) . . . . ?
N1 C3 C4 C5 -176.6(8) . . . . ?
C3 C4 C5 C6 -179.4(8) . . . . ?
N2 C4 C5 C6 4.3(10) . . . . ?
C3 C4 C5 C25 7.1(13) . . . . ?
N2 C4 C5 C25 -169.2(6) . . . . ?
C4 C5 C6 C7 1.1(10) . . . . ?
C25 C5 C6 C7 174.3(7) . . . . ?
C4 C5 C6 C23 -176.2(6) . . . . ?
C25 C5 C6 C23 -3.0(10) . . . . ?
C5 C6 C7 C22 177.4(6) . . . . ?
C23 C6 C7 C22 -5.3(10) . . . . ?
C5 C6 C7 C8 -4.9(10) . . . . ?
C23 C6 C7 C8 172.4(6) . . . . ?
C22 C7 C8 C9 1.0(10) . . . . ?
C6 C7 C8 C9 -176.9(6) . . . . ?
C22 C7 C8 N2 -179.0(5) . . . . ?
C6 C7 C8 N2 3.1(9) . . . . ?
N2 C8 C9 C20 179.1(5) . . . . ?
C7 C8 C9 C20 -0.9(10) . . . . ?
N2 C8 C9 C10 -4.9(9) . . . . ?
C7 C8 C9 C10 175.1(6) . . . . ?
C8 C9 C10 C11 4.9(10) . . . . ?
C20 C9 C10 C11 -179.5(6) . . . . ?
C8 C9 C10 C18 -170.9(7) . . . . ?
C20 C9 C10 C18 4.7(11) . . . . ?
C9 C10 C11 C1 1.7(10) . . . . ?
C18 C10 C11 C1 177.4(7) . . . . ?
C9 C10 C11 C12 -171.7(7) . . . . ?
C18 C10 C11 C12 4.0(11) . . . . ?
N2 C1 C11 C10 -8.2(10) . . . . ?
N1 C1 C11 C10 178.3(7) . . . . ?
N2 C1 C11 C12 165.3(7) . . . . ?
N1 C1 C11 C12 -8.1(12) . . . . ?
C10 C11 C12 C17 -80.4(10) . . . . ?
C1 C11 C12 C17 106.3(9) . . . . ?
C10 C11 C12 C13 97.6(9) . . . . ?
C1 C11 C12 C13 -75.7(10) . . . . ?
C17 C12 C13 C14 -4.2(13) . . . . ?
C11 C12 C13 C14 177.8(8) . . . . ?
C12 C13 C14 C15 4.5(14) . . . . ?
C13 C14 C15 C16 -3.4(15) . . . . ?
C14 C15 C16 C17 2.2(15) . . . . ?
C13 C12 C17 C16 2.8(13) . . . . ?
C11 C12 C17 C16 -179.2(8) . . . . ?
C15 C16 C17 C12 -1.9(15) . . . . ?
C11 C10 C18 C19 -97.3(9) . . . . ?
C9 C10 C18 C19 78.5(9) . . . . ?
C8 C9 C20 C21 -0.6(10) . . . . ?
C10 C9 C20 C21 -176.4(7) . . . . ?
C9 C20 C21 C22 2.0(11) . . . . ?
C8 C7 C22 C21 0.4(10) . . . . ?
C6 C7 C22 C21 178.2(7) . . . . ?
C20 C21 C22 C7 -1.8(11) . . . . ?
C5 C6 C23 C24 97.3(8) . . . . ?
C7 C6 C23 C24 -80.0(9) . . . . ?
C6 C5 C25 C26 93.7(10) . . . . ?
C4 C5 C25 C26 -93.0(10) . . . . ?
C6 C5 C25 C30 -90.2(10) . . . . ?
C4 C5 C25 C30 83.0(9) . . . . ?
C30 C25 C26 C27 6.4(16) . . . . ?
C5 C25 C26 C27 -177.5(10) . . . . ?
C25 C26 C27 C28 -6(2) . . . . ?
C26 C27 C28 C29 2(2) . . . . ?
C27 C28 C29 C30 1.2(18) . . . . ?
C26 C25 C30 C29 -2.9(15) . . . . ?
C5 C25 C30 C29 -179.1(9) . . . . ?
C28 C29 C30 C25 -1.0(17) . . . . ?
C4 C3 N1 C1 -0.1(9) . . . . ?
C4 C3 N1 C2 -175.1(8) . . . . ?
N2 C1 N1 C3 0.1(8) . . . . ?
C11 C1 N1 C3 174.3(8) . . . . ?
N2 C1 N1 C2 174.9(8) . . . . ?
C11 C1 N1 C2 -10.9(14) . . . . ?
N1 C1 N2 C4 -0.1(8) . . . . ?
C11 C1 N2 C4 -175.3(6) . . . . ?
N1 C1 N2 C8 -176.3(5) . . . . ?
C11 C1 N2 C8 8.5(10) . . . . ?
C3 C4 N2 C1 0.1(8) . . . . ?
C5 C4 N2 C1 177.4(6) . . . . ?
C3 C4 N2 C8 176.1(6) . . . . ?
C5 C4 N2 C8 -6.6(10) . . . . ?
C9 C8 N2 C1 -1.6(9) . . . . ?
C7 C8 N2 C1 178.3(6) . . . . ?
C9 C8 N2 C4 -177.2(6) . . . . ?
C7 C8 N2 C4 2.8(9) . . . . ?
F2 C31 S1 O1 60.0(16) . . . . ?
F1 C31 S1 O1 -179.7(16) . . . . ?
F3 C31 S1 O1 -60.8(16) . . . . ?
F2 C31 S1 O2 -85.6(16) . . . . ?
F1 C31 S1 O2 34.7(17) . . . . ?
F3 C31 S1 O2 153.6(16) . . . . ?
F2 C31 S1 O3 170.9(15) . . . . ?
F1 C31 S1 O3 -68.8(16) . . . . ?
F3 C31 S1 O3 50.2(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
C3 H3 O1 0.93 2.61 3.365(17) 138.3 .
C3 H3 O1 0.93 2.61 3.365(17) 138.3 .

_refine_diff_density_max         1.380
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.132

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1914692'
loop_
_audit_author_name
_audit_author_address
'Pirudhan Karak'
;Indian Institute of Science Education and Research Bhopal
India
;
_audit_update_record             
;
2019-05-08 deposited with the CCDC.	2019-05-20 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         ?
_chemical_formula_sum            'C50 H34 Cl3 N5'
_chemical_formula_weight         811.17

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'
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                   12.0477(13)
_cell_length_b                   13.2688(15)
_cell_length_c                   13.3384(13)
_cell_angle_alpha                73.550(4)
_cell_angle_beta                 79.747(4)
_cell_angle_gamma                77.163(4)
_cell_volume                     1978.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    5958
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      26.00

_exptl_crystal_description       'needle shape'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.276
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42672
_diffrn_reflns_av_unetI/netI     0.2009
_diffrn_reflns_av_R_equivalents  0.1740
_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       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.222
_diffrn_reflns_theta_max         28.809
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10232
_reflns_number_gt                4564
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0906P)²+7.7500P] 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         10232
_refine_ls_number_parameters     525
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2775
_refine_ls_R_factor_gt           0.1369
_refine_ls_wR_factor_ref         0.3156
_refine_ls_wR_factor_gt          0.2593
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
Cl01 Cl 0.17164(19) 0.36552(19) -0.10817(18) 0.0781(7) Uani 1 1 d . . . . .
Cl02 Cl 0.19928(19) 0.1883(2) 0.0735(2) 0.1003(10) Uani 1 1 d . . . . .
Cl03 Cl 0.0371(2) 0.3782(3) 0.0881(2) 0.1026(10) Uani 1 1 d . . . . .
N3 N 0.4234(4) 0.6132(3) 0.2258(3) 0.0242(10) Uani 1 1 d . . . . .
N1 N 0.7020(4) 0.3684(3) 0.0837(3) 0.0242(10) Uani 1 1 d . . . . .
N4 N 0.2838(4) 0.7412(4) 0.2759(4) 0.0293(11) Uani 1 1 d . . . . .
N2 N 0.8504(4) 0.2671(4) 0.0061(4) 0.0304(11) Uani 1 1 d . . . . .
N5 N 0.5634(4) 0.4916(4) 0.1552(3) 0.0245(10) Uani 1 1 d . . . . .
C4 C 0.3335(4) 0.6402(4) 0.3023(4) 0.0247(12) Uani 1 1 d . . . . .
C9 C 0.5318(5) 0.3335(4) 0.3403(4) 0.0260(13) Uani 1 1 d . . . . .
H00A H 0.518912 0.278384 0.402173 0.031 Uiso 1 1 calc R U . . .
C00B C 0.2156(5) 0.5994(4) 0.4786(4) 0.0287(13) Uani 1 1 d . . . . .
C10 C 0.6168(4) 0.3103(4) 0.2616(4) 0.0224(12) Uani 1 1 d . . . . .
C00D C 0.3079(4) 0.5614(4) 0.3995(4) 0.0246(12) Uani 1 1 d . . . . .
C2 C 0.8197(5) 0.3638(4) -0.0640(4) 0.0273(13) Uani 1 1 d . . . . .
C8 C 0.4641(4) 0.4348(4) 0.3325(4) 0.0235(12) Uani 1 1 d . . . . .
C00G C 0.6855(4) 0.1268(4) 0.3772(4) 0.0266(13) Uani 1 1 d . . . . .
C00H C 0.3737(4) 0.4617(4) 0.4144(4) 0.0232(12) Uani 1 1 d . . . . .
C00I C 0.7768(5) 0.1895(4) 0.1920(4) 0.0269(13) Uani 1 1 d . . . . .
C00J C 0.6961(4) 0.2081(4) 0.2728(4) 0.0243(12) Uani 1 1 d . . . . .
C11 C 0.6252(4) 0.3928(4) 0.1677(4) 0.0245(12) Uani 1 1 d . . . . .
C3 C 0.7271(5) 0.4285(4) -0.0198(4) 0.0262(13) Uani 1 1 d . . . . .
C1 C 0.7796(5) 0.2713(4) 0.0929(4) 0.0266(12) Uani 1 1 d . . . . .
C5 C 0.4285(4) 0.7073(4) 0.1450(4) 0.0262(13) Uani 1 1 d . . . . .
C00O C 0.3570(5) 0.3765(4) 0.5128(4) 0.0269(12) Uani 1 1 d . . . . .
C00P C 0.7063(5) 0.1463(5) 0.4684(4) 0.0319(14) Uani 1 1 d . . . . .
H00P H 0.728047 0.211747 0.465322 0.038 Uiso 1 1 calc R U . . .
C7 C 0.4880(4) 0.5111(4) 0.2361(4) 0.0229(12) Uani 1 1 d . . . . .
C00R C 0.1111(5) 0.6595(5) 0.4481(5) 0.0313(13) Uani 1 1 d . . . . .
H00R H 0.097442 0.673802 0.377014 0.038 Uiso 1 1 calc R U . . .
C6 C 0.3403(5) 0.7840(4) 0.1789(4) 0.0290(13) Uani 1 1 d . . . . .
C00T C 0.2317(5) 0.5786(4) 0.5841(4) 0.0310(13) Uani 1 1 d . . . . .
H00T H 0.301881 0.536956 0.607155 0.037 Uiso 1 1 calc R U . . .
C00U C 0.8645(5) 0.0896(5) 0.1989(5) 0.0317(14) Uani 1 1 d . . . . .
C00V C 0.7291(6) 0.5634(5) -0.1793(4) 0.0376(16) Uani 1 1 d . . . . .
H00V H 0.698901 0.631826 -0.220694 0.045 Uiso 1 1 calc R U . . .
C00W C 0.8688(5) 0.4015(5) -0.1674(5) 0.0359(15) Uani 1 1 d . . . . .
H00W H 0.932508 0.359002 -0.198230 0.043 Uiso 1 1 calc R U . . .
C00X C 0.6954(5) 0.0702(5) 0.5646(5) 0.0368(15) Uani 1 1 d . . . . .
H00X H 0.709169 0.084632 0.626696 0.044 Uiso 1 1 calc R U . . .
C00Y C 0.2511(5) 0.3434(5) 0.5469(4) 0.0328(14) Uani 1 1 d . . . . .
H00Y H 0.188600 0.374158 0.506787 0.039 Uiso 1 1 calc R U . . .
C00Z C 0.9318(5) 0.0531(5) 0.2804(5) 0.0417(16) Uani 1 1 d . . . . .
H00Z H 0.923349 0.092105 0.331919 0.050 Uiso 1 1 calc R U . . .
C010 C 0.0273(5) 0.6988(5) 0.5194(6) 0.0429(17) Uani 1 1 d . . . . .
H010 H -0.043300 0.739899 0.496860 0.051 Uiso 1 1 calc R U . . .
C011 C 0.5030(5) 0.7338(5) 0.0533(4) 0.0323(14) Uani 1 1 d . . . . .
H011 H 0.564720 0.682649 0.032216 0.039 Uiso 1 1 calc R U . . .
C012 C 0.4459(6) 0.3299(5) 0.5737(5) 0.0377(15) Uani 1 1 d . . . . .
H012 H 0.517840 0.352532 0.551461 0.045 Uiso 1 1 calc R U . . .
C013 C 0.8230(6) 0.5013(5) -0.2232(5) 0.0398(16) Uani 1 1 d . . . . .
H013 H 0.856015 0.528508 -0.293299 0.048 Uiso 1 1 calc R U . . .
C014 C 0.6651(5) -0.0253(5) 0.5705(5) 0.0420(16) Uani 1 1 d . . . . .
C015 C 0.6776(5) 0.5288(5) -0.0764(4) 0.0327(14) Uani 1 1 d . . . . .
H015 H 0.612655 0.571089 -0.046799 0.039 Uiso 1 1 calc R U . . .
C016 C 0.8817(5) 0.0307(5) 0.1225(5) 0.0393(15) Uani 1 1 d . . . . .
H016 H 0.838897 0.055938 0.064193 0.047 Uiso 1 1 calc R U . . .
C017 C 0.2385(7) 0.2642(5) 0.6413(5) 0.0473(18) Uani 1 1 d . . . . .
H017 H 0.166829 0.241425 0.665453 0.057 Uiso 1 1 calc R U . . .
C018 C 0.4823(6) 0.8383(5) -0.0055(5) 0.0440(17) Uani 1 1 d . . . . .
H018 H 0.530874 0.859029 -0.069280 0.053 Uiso 1 1 calc R U . . .
C019 C 0.0450(6) 0.6788(6) 0.6234(5) 0.0474(18) Uani 1 1 d . . . . .
H019 H -0.012476 0.706713 0.672232 0.057 Uiso 1 1 calc R U . . .
C01A C 0.6543(5) 0.0304(5) 0.3834(5) 0.0378(15) Uani 1 1 d . . . . .
H01A H 0.639718 0.015630 0.321786 0.045 Uiso 1 1 calc R U . . .
C01B C 0.3213(5) 0.8892(5) 0.1176(5) 0.0372(15) Uani 1 1 d . . . . .
H01B H 0.261095 0.941411 0.138964 0.045 Uiso 1 1 calc R U . . .
C01C C 1.0252(6) -0.0997(6) 0.2126(6) 0.0516(19) Uani 1 1 d . . . . .
H01C H 1.079084 -0.164640 0.217916 0.062 Uiso 1 1 calc R U . . .
C01D C 0.3933(5) 0.9148(5) 0.0247(5) 0.0438(17) Uani 1 1 d . . . . .
H01D H 0.381729 0.985530 -0.019128 0.053 Uiso 1 1 calc R U . . .
C01E C 0.6443(6) -0.0444(5) 0.4797(5) 0.0477(17) Uani 1 1 d . . . . .
H01E H 0.622699 -0.110105 0.483214 0.057 Uiso 1 1 calc R U . . .
C01F C 1.0131(5) -0.0425(6) 0.2864(6) 0.054(2) Uani 1 1 d . . . . .
H01F H 1.059776 -0.067597 0.342032 0.065 Uiso 1 1 calc R U . . .
C01G C 0.4327(7) 0.2528(5) 0.6642(5) 0.0504(19) Uani 1 1 d . . . . .
H01G H 0.495695 0.221927 0.703680 0.060 Uiso 1 1 calc R U . . .
C01H C 0.1479(6) 0.6175(5) 0.6555(5) 0.0424(17) Uani 1 1 d . . . . .
H01H H 0.160568 0.602222 0.726954 0.051 Uiso 1 1 calc R U . . .
C01I C 0.9604(6) -0.0632(5) 0.1325(6) 0.0487(18) Uani 1 1 d . . . . .
H01I H 0.969261 -0.103199 0.081825 0.058 Uiso 1 1 calc R U . . .
C01J C 0.1028(6) 0.2929(6) 0.0060(5) 0.0518(19) Uani 1 1 d . . . . .
H01J H 0.042502 0.262900 -0.012943 0.062 Uiso 1 1 calc R U . . .
C01K C 0.3299(8) 0.2186(5) 0.7000(5) 0.056(2) Uani 1 1 d . . . . .
C01L C 0.6538(8) -0.1088(7) 0.6768(6) 0.081(3) Uani 1 1 d . . . . .
H01K H 0.572584 -0.105176 0.705239 0.121 Uiso 1 1 calc R U . . .
H01L H 0.695481 -0.093994 0.726210 0.121 Uiso 1 1 calc R U . . .
H01M H 0.686019 -0.180299 0.666648 0.121 Uiso 1 1 calc R U . . .
C01M C 0.3292(11) 0.1337(8) 0.8020(7) 0.102(4) Uani 1 1 d . . . . .
H01N H 0.397047 0.077569 0.798396 0.153 Uiso 1 1 calc R U . . .
H01O H 0.259785 0.102754 0.814301 0.153 Uiso 1 1 calc R U . . .
H01P H 0.330333 0.165263 0.859817 0.153 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
Cl01 C01J 1.735(7) . ?
Cl02 C01J 1.742(7) . ?
Cl03 C01J 1.762(7) . ?
N3 C7 1.387(7) . ?
N3 C5 1.405(6) . ?
N3 C4 1.408(7) . ?
N1 C11 1.385(7) . ?
N1 C1 1.401(7) . ?
N1 C3 1.403(7) . ?
N4 C4 1.316(7) . ?
N4 C6 1.379(7) . ?
N2 C1 1.318(7) . ?
N2 C2 1.375(7) . ?
N5 C7 1.328(7) . ?
N5 C11 1.337(7) . ?
C4 C00D 1.450(7) . ?
C9 C10 1.381(8) . ?
C9 C8 1.395(7) . ?
C9 H00A 0.9500 . ?
C00B C00R 1.392(8) . ?
C00B C00T 1.397(8) . ?
C00B C00D 1.496(8) . ?
C10 C11 1.416(7) . ?
C10 C00J 1.461(7) . ?
C00D C00H 1.364(7) . ?
C2 C00W 1.397(8) . ?
C2 C3 1.399(8) . ?
C8 C7 1.421(7) . ?
C8 C00H 1.460(8) . ?
C00G C00P 1.387(8) . ?
C00G C01A 1.388(8) . ?
C00G C00J 1.505(7) . ?
C00H C00O 1.485(7) . ?
C00I C00J 1.357(8) . ?
C00I C1 1.455(8) . ?
C00I C00U 1.491(8) . ?
C3 C015 1.391(8) . ?
C5 C011 1.389(8) . ?
C5 C6 1.407(8) . ?
C00O C012 1.386(8) . ?
C00O C00Y 1.400(8) . ?
C00P C00X 1.396(8) . ?
C00P H00P 0.9500 . ?
C00R C010 1.379(9) . ?
C00R H00R 0.9500 . ?
C6 C01B 1.395(8) . ?
C00T C01H 1.377(9) . ?
C00T H00T 0.9500 . ?
C00U C00Z 1.384(8) . ?
C00U C016 1.412(9) . ?
C00V C013 1.387(9) . ?
C00V C015 1.395(8) . ?
C00V H00V 0.9500 . ?
C00W C013 1.370(9) . ?
C00W H00W 0.9500 . ?
C00X C014 1.372(9) . ?
C00X H00X 0.9500 . ?
C00Y C017 1.403(8) . ?
C00Y H00Y 0.9500 . ?
C00Z C01F 1.412(9) . ?
C00Z H00Z 0.9500 . ?
C010 C019 1.383(9) . ?
C010 H010 0.9500 . ?
C011 C018 1.379(8) . ?
C011 H011 0.9500 . ?
C012 C01G 1.354(9) . ?
C012 H012 0.9500 . ?
C013 H013 0.9500 . ?
C014 C01E 1.380(9) . ?
C014 C01L 1.538(9) . ?
C015 H015 0.9500 . ?
C016 C01I 1.376(9) . ?
C016 H016 0.9500 . ?
C017 C01K 1.391(10) . ?
C017 H017 0.9500 . ?
C018 C01D 1.391(9) . ?
C018 H018 0.9500 . ?
C019 C01H 1.388(10) . ?
C019 H019 0.9500 . ?
C01A C01E 1.388(9) . ?
C01A H01A 0.9500 . ?
C01B C01D 1.383(9) . ?
C01B H01B 0.9500 . ?
C01C C01I 1.350(10) . ?
C01C C01F 1.374(11) . ?
C01C H01C 0.9500 . ?
C01D H01D 0.9500 . ?
C01E H01E 0.9500 . ?
C01F H01F 0.9500 . ?
C01G C01K 1.373(11) . ?
C01G H01G 0.9500 . ?
C01H H01H 0.9500 . ?
C01I H01I 0.9500 . ?
C01J H01J 1.0000 . ?
C01K C01M 1.500(10) . ?
C01L H01K 0.9800 . ?
C01L H01L 0.9800 . ?
C01L H01M 0.9800 . ?
C01M H01N 0.9800 . ?
C01M H01O 0.9800 . ?
C01M H01P 0.9800 . ?

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
C7 N3 C5 131.0(5) . . ?
C7 N3 C4 122.9(4) . . ?
C5 N3 C4 106.0(4) . . ?
C11 N1 C1 122.5(4) . . ?
C11 N1 C3 131.9(5) . . ?
C1 N1 C3 105.6(4) . . ?
C4 N4 C6 105.5(5) . . ?
C1 N2 C2 105.1(5) . . ?
C7 N5 C11 116.8(4) . . ?
N4 C4 N3 112.5(5) . . ?
N4 C4 C00D 127.0(5) . . ?
N3 C4 C00D 120.4(5) . . ?
C10 C9 C8 122.5(5) . . ?
C10 C9 H00A 118.8 . . ?
C8 C9 H00A 118.8 . . ?
C00R C00B C00T 117.8(5) . . ?
C00R C00B C00D 120.6(5) . . ?
C00T C00B C00D 121.6(5) . . ?
C9 C10 C11 116.1(5) . . ?
C9 C10 C00J 123.1(5) . . ?
C11 C10 C00J 120.7(5) . . ?
C00H C00D C4 118.1(5) . . ?
C00H C00D C00B 125.4(5) . . ?
C4 C00D C00B 116.5(5) . . ?
N2 C2 C00W 128.6(5) . . ?
N2 C2 C3 111.6(5) . . ?
C00W C2 C3 119.7(5) . . ?
C9 C8 C7 114.6(5) . . ?
C9 C8 C00H 123.7(5) . . ?
C7 C8 C00H 121.7(5) . . ?
C00P C00G C01A 118.8(5) . . ?
C00P C00G C00J 121.1(5) . . ?
C01A C00G C00J 120.0(5) . . ?
C00D C00H C8 120.4(5) . . ?
C00D C00H C00O 122.2(5) . . ?
C8 C00H C00O 117.4(5) . . ?
C00J C00I C1 118.7(5) . . ?
C00J C00I C00U 123.7(5) . . ?
C1 C00I C00U 117.6(5) . . ?
C00I C00J C10 120.4(5) . . ?
C00I C00J C00G 122.2(5) . . ?
C10 C00J C00G 117.4(5) . . ?
N5 C11 N1 118.5(5) . . ?
N5 C11 C10 124.1(5) . . ?
N1 C11 C10 117.4(5) . . ?
C015 C3 C2 122.5(5) . . ?
C015 C3 N1 132.6(5) . . ?
C2 C3 N1 104.8(5) . . ?
N2 C1 N1 112.9(5) . . ?
N2 C1 C00I 127.2(5) . . ?
N1 C1 C00I 119.9(5) . . ?
C011 C5 N3 133.4(5) . . ?
C011 C5 C6 121.9(5) . . ?
N3 C5 C6 104.5(5) . . ?
C012 C00O C00Y 118.7(5) . . ?
C012 C00O C00H 120.4(5) . . ?
C00Y C00O C00H 120.9(5) . . ?
C00G C00P C00X 120.4(5) . . ?
C00G C00P H00P 119.8 . . ?
C00X C00P H00P 119.8 . . ?
N5 C7 N3 118.1(5) . . ?
N5 C7 C8 125.5(5) . . ?
N3 C7 C8 116.3(5) . . ?
C010 C00R C00B 121.1(6) . . ?
C010 C00R H00R 119.5 . . ?
C00B C00R H00R 119.5 . . ?
N4 C6 C01B 128.1(6) . . ?
N4 C6 C5 111.5(5) . . ?
C01B C6 C5 120.3(5) . . ?
C01H C00T C00B 121.2(6) . . ?
C01H C00T H00T 119.4 . . ?
C00B C00T H00T 119.4 . . ?
C00Z C00U C016 118.5(6) . . ?
C00Z C00U C00I 120.3(6) . . ?
C016 C00U C00I 121.2(5) . . ?
C013 C00V C015 122.3(6) . . ?
C013 C00V H00V 118.9 . . ?
C015 C00V H00V 118.9 . . ?
C013 C00W C2 118.4(6) . . ?
C013 C00W H00W 120.8 . . ?
C2 C00W H00W 120.8 . . ?
C014 C00X C00P 120.7(6) . . ?
C014 C00X H00X 119.7 . . ?
C00P C00X H00X 119.7 . . ?
C00O C00Y C017 119.0(6) . . ?
C00O C00Y H00Y 120.5 . . ?
C017 C00Y H00Y 120.5 . . ?
C00U C00Z C01F 119.4(7) . . ?
C00U C00Z H00Z 120.3 . . ?
C01F C00Z H00Z 120.3 . . ?
C00R C010 C019 120.5(6) . . ?
C00R C010 H010 119.7 . . ?
C019 C010 H010 119.7 . . ?
C018 C011 C5 116.4(6) . . ?
C018 C011 H011 121.8 . . ?
C5 C011 H011 121.8 . . ?
C01G C012 C00O 121.6(7) . . ?
C01G C012 H012 119.2 . . ?
C00O C012 H012 119.2 . . ?
C00W C013 C00V 121.2(6) . . ?
C00W C013 H013 119.4 . . ?
C00V C013 H013 119.4 . . ?
C00X C014 C01E 118.9(6) . . ?
C00X C014 C01L 120.3(6) . . ?
C01E C014 C01L 120.8(7) . . ?
C3 C015 C00V 115.8(6) . . ?
C3 C015 H015 122.1 . . ?
C00V C015 H015 122.1 . . ?
C01I C016 C00U 120.1(6) . . ?
C01I C016 H016 119.9 . . ?
C00U C016 H016 119.9 . . ?
C01K C017 C00Y 120.7(7) . . ?
C01K C017 H017 119.7 . . ?
C00Y C017 H017 119.7 . . ?
C011 C018 C01D 122.7(6) . . ?
C011 C018 H018 118.7 . . ?
C01D C018 H018 118.7 . . ?
C010 C019 C01H 119.1(6) . . ?
C010 C019 H019 120.5 . . ?
C01H C019 H019 120.5 . . ?
C01E C01A C00G 120.0(6) . . ?
C01E C01A H01A 120.0 . . ?
C00G C01A H01A 120.0 . . ?
C01D C01B C6 117.7(6) . . ?
C01D C01B H01B 121.2 . . ?
C6 C01B H01B 121.2 . . ?
C01I C01C C01F 119.8(6) . . ?
C01I C01C H01C 120.1 . . ?
C01F C01C H01C 120.1 . . ?
C01B C01D C018 120.9(5) . . ?
C01B C01D H01D 119.5 . . ?
C018 C01D H01D 119.5 . . ?
C014 C01E C01A 121.3(6) . . ?
C014 C01E H01E 119.4 . . ?
C01A C01E H01E 119.4 . . ?
C01C C01F C00Z 120.6(6) . . ?
C01C C01F H01F 119.7 . . ?
C00Z C01F H01F 119.7 . . ?
C012 C01G C01K 121.2(6) . . ?
C012 C01G H01G 119.4 . . ?
C01K C01G H01G 119.4 . . ?
C00T C01H C019 120.3(6) . . ?
C00T C01H H01H 119.8 . . ?
C019 C01H H01H 119.8 . . ?
C01C C01I C016 121.5(7) . . ?
C01C C01I H01I 119.3 . . ?
C016 C01I H01I 119.3 . . ?
Cl01 C01J Cl02 111.1(4) . . ?
Cl01 C01J Cl03 109.2(4) . . ?
Cl02 C01J Cl03 109.2(4) . . ?
Cl01 C01J H01J 109.1 . . ?
Cl02 C01J H01J 109.1 . . ?
Cl03 C01J H01J 109.1 . . ?
C01G C01K C017 118.8(6) . . ?
C01G C01K C01M 114.5(8) . . ?
C017 C01K C01M 126.6(9) . . ?
C014 C01L H01K 109.5 . . ?
C014 C01L H01L 109.5 . . ?
H01K C01L H01L 109.5 . . ?
C014 C01L H01M 109.5 . . ?
H01K C01L H01M 109.5 . . ?
H01L C01L H01M 109.5 . . ?
C01K C01M H01N 109.5 . . ?
C01K C01M H01O 109.5 . . ?
H01N C01M H01O 109.5 . . ?
C01K C01M H01P 109.5 . . ?
H01N C01M H01P 109.5 . . ?
H01O C01M H01P 109.5 . . ?

_refine_diff_density_max         1.190
_refine_diff_density_min         -0.988
_refine_diff_density_rms         0.104



####################################################################### 
# 
# 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_shelx_CCDC4
_audit_block_doi                 10.5517/cc141pvq
_database_code_depnum_ccdc_archive 'CCDC 1044323'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acscatal.5b00243 2015
_audit_update_record             
;
2015-09-18 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C60 H46 Cl2 F3 N4 O3 Rh S'
_chemical_formula_weight         1133.88

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'
Rh Rh -1.1178 0.9187 '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                   13.2046(2)
_cell_length_b                   13.3746(2)
_cell_length_c                   16.1248(3)
_cell_angle_alpha                77.0700(10)
_cell_angle_beta                 72.2960(10)
_cell_angle_gamma                71.9590(10)
_cell_volume                     2552.96(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.543
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35119
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.339
_diffrn_reflns_theta_max         24.407
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.910
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.910
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.910
_reflns_number_total             8392
_reflns_number_gt                7144
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_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)+(0.0600P)²+4.1399P] 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         8392
_refine_ls_number_parameters     667
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1139
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
C1 C 0.3987(3) 0.0485(3) 0.6695(2) 0.0198(8) Uani 1 1 d . . . . .
C2 C 0.5735(3) -0.0021(3) 0.7227(3) 0.0374(10) Uani 1 1 d . . . . .
C3 C 0.4294(3) 0.1742(3) 0.7217(2) 0.0253(8) Uani 1 1 d . . . . .
H3 H 0.4641 0.2076 0.7454 0.030 Uiso 1 1 calc R U . . .
C4 C 0.3316(3) 0.2201(3) 0.6997(2) 0.0227(8) Uani 1 1 d . . . . .
C5 C 0.2209(3) 0.1500(3) 0.6456(2) 0.0193(7) Uani 1 1 d . . . . .
C6 C 0.1457(3) 0.2489(3) 0.6557(2) 0.0202(8) Uani 1 1 d . . . . .
C7 C 0.0498(3) 0.2607(3) 0.6320(2) 0.0230(8) Uani 1 1 d . . . . .
H7 H -0.0053 0.3238 0.6378 0.028 Uiso 1 1 calc R U . . .
C8 C 0.0341(3) 0.1793(3) 0.5993(2) 0.0256(8) Uani 1 1 d . . . . .
H8 H -0.0306 0.1911 0.5826 0.031 Uiso 1 1 calc R U . . .
C9 C 0.1108(3) 0.0827(3) 0.5909(2) 0.0233(8) Uani 1 1 d . . . . .
H9 H 0.0976 0.0302 0.5694 0.028 Uiso 1 1 calc R U . . .
C10 C 0.2103(3) 0.0644(3) 0.6157(2) 0.0207(8) Uani 1 1 d . . . . .
C11 C 0.2991(3) -0.0324(3) 0.6118(2) 0.0217(8) Uani 1 1 d . . . . .
C12 C 0.3924(3) -0.0415(3) 0.6383(2) 0.0229(8) Uani 1 1 d . . . . .
C13 C 0.4835(3) -0.1405(3) 0.6394(2) 0.0222(8) Uani 1 1 d . . . . .
C14 C 0.5878(3) -0.1444(3) 0.5833(3) 0.0288(9) Uani 1 1 d . . . . .
H14 H 0.5993 -0.0869 0.5403 0.035 Uiso 1 1 calc R U . . .
C15 C 0.6746(3) -0.2332(3) 0.5910(3) 0.0317(9) Uani 1 1 d . . . . .
H15 H 0.7444 -0.2351 0.5540 0.038 Uiso 1 1 calc R U . . .
C16 C 0.6567(3) -0.3193(3) 0.6542(3) 0.0311(9) Uani 1 1 d . . . . .
H16 H 0.7152 -0.3783 0.6607 0.037 Uiso 1 1 calc R U . . .
C17 C 0.5526(3) -0.3180(3) 0.7075(3) 0.0314(9) Uani 1 1 d . . . . .
H17 H 0.5402 -0.3771 0.7482 0.038 Uiso 1 1 calc R U . . .
C18 C 0.4670(3) -0.2290(3) 0.7002(2) 0.0275(9) Uani 1 1 d . . . . .
H18 H 0.3971 -0.2282 0.7367 0.033 Uiso 1 1 calc R U . . .
C19 C 0.2896(3) -0.1215(3) 0.5760(2) 0.0230(8) Uani 1 1 d . . . . .
C20 C 0.3615(3) -0.1534(3) 0.4975(2) 0.0253(8) Uani 1 1 d . . . . .
H20 H 0.4201 -0.1231 0.4701 0.030 Uiso 1 1 calc R U . . .
C21 C 0.3468(3) -0.2296(3) 0.4598(3) 0.0281(9) Uani 1 1 d . . . . .
H21 H 0.3947 -0.2491 0.4069 0.034 Uiso 1 1 calc R U . . .
C22 C 0.2615(3) -0.2767(3) 0.5004(3) 0.0298(9) Uani 1 1 d . . . . .
H22 H 0.2512 -0.3272 0.4747 0.036 Uiso 1 1 calc R U . . .
C23 C 0.1916(3) -0.2486(3) 0.5793(3) 0.0345(10) Uani 1 1 d . . . . .
H23 H 0.1353 -0.2817 0.6076 0.041 Uiso 1 1 calc R U . . .
C24 C 0.2049(3) -0.1713(3) 0.6169(3) 0.0311(9) Uani 1 1 d . . . . .
H24 H 0.1567 -0.1524 0.6698 0.037 Uiso 1 1 calc R U . . .
C25 C 0.2703(3) 0.4894(3) 0.6847(3) 0.0274(9) Uani 1 1 d . . . . .
C26 C 0.2762(3) 0.4668(3) 0.6003(2) 0.0240(8) Uani 1 1 d . . . . .
C27 C 0.1674(3) 0.4839(3) 0.5939(2) 0.0226(8) Uani 1 1 d . . . . .
C28 C 0.0923(3) 0.5114(3) 0.6761(2) 0.0248(8) Uani 1 1 d . . . . .
C29 C 0.1571(3) 0.5170(3) 0.7312(3) 0.0274(9) Uani 1 1 d . . . . .
C30 C 0.1113(4) 0.5525(4) 0.8199(3) 0.0403(10) Uani 1 1 d . . . . .
H30A H 0.0326 0.5659 0.8358 0.060 Uiso 1 1 calc R U . . .
H30B H 0.1410 0.4979 0.8626 0.060 Uiso 1 1 calc R U . . .
H30C H 0.1310 0.6164 0.8183 0.060 Uiso 1 1 calc R U . . .
C31 C -0.0312(3) 0.5451(3) 0.6948(3) 0.0329(9) Uani 1 1 d . . . . .
H31A H -0.0535 0.5330 0.6473 0.049 Uiso 1 1 calc R U . . .
H31B H -0.0620 0.5046 0.7485 0.049 Uiso 1 1 calc R U . . .
H31C H -0.0569 0.6193 0.7005 0.049 Uiso 1 1 calc R U . . .
C32 C 0.1358(3) 0.4833(3) 0.5131(3) 0.0304(9) Uani 1 1 d . . . . .
H32A H 0.0573 0.4969 0.5258 0.046 Uiso 1 1 calc R U . . .
H32B H 0.1598 0.5375 0.4679 0.046 Uiso 1 1 calc R U . . .
H32C H 0.1700 0.4152 0.4935 0.046 Uiso 1 1 calc R U . . .
C33 C 0.3797(3) 0.4386(3) 0.5294(3) 0.0318(9) Uani 1 1 d . . . . .
H33A H 0.4420 0.4316 0.5510 0.048 Uiso 1 1 calc R U . . .
H33B H 0.3852 0.3726 0.5120 0.048 Uiso 1 1 calc R U . . .
H33C H 0.3781 0.4936 0.4796 0.048 Uiso 1 1 calc R U . . .
C34 C 0.3671(4) 0.4975(4) 0.7107(3) 0.0403(11) Uani 1 1 d . . . . .
H34A H 0.4335 0.4733 0.6669 0.060 Uiso 1 1 calc R U . . .
H34B H 0.3585 0.5701 0.7154 0.060 Uiso 1 1 calc R U . . .
H34C H 0.3713 0.4542 0.7663 0.060 Uiso 1 1 calc R U . . .
C35 C 0.1326(3) 0.2143(3) 0.9690(2) 0.0233(8) Uani 1 1 d . . . . .
C36 C 0.2846(3) 0.3044(4) 0.8888(3) 0.0348(10) Uani 1 1 d . . . . .
C37 C 0.1389(3) 0.2823(3) 0.8253(2) 0.0233(8) Uani 1 1 d . . . . .
C38 C 0.0505(3) 0.2406(3) 0.8610(2) 0.0219(8) Uani 1 1 d . . . . .
H38 H 0.0005 0.2401 0.8311 0.026 Uiso 1 1 calc R U . . .
C39 C -0.0280(3) 0.1468(3) 1.0098(2) 0.0244(8) Uani 1 1 d . . . . .
C40 C -0.1178(3) 0.1356(3) 0.9885(2) 0.0268(8) Uani 1 1 d . . . . .
H40 H -0.1299 0.1640 0.9331 0.032 Uiso 1 1 calc R U . . .
C41 C -0.1890(3) 0.0823(3) 1.0497(3) 0.0293(9) Uani 1 1 d . . . . .
H41 H -0.2494 0.0746 1.0359 0.035 Uiso 1 1 calc R U . . .
C42 C -0.1696(3) 0.0399(3) 1.1327(3) 0.0317(9) Uani 1 1 d . . . . .
H42 H -0.2166 0.0026 1.1737 0.038 Uiso 1 1 calc R U . . .
C43 C -0.0838(3) 0.0524(3) 1.1541(3) 0.0303(9) Uani 1 1 d . . . . .
H43 H -0.0732 0.0240 1.2099 0.036 Uiso 1 1 calc R U . . .
C44 C -0.0095(3) 0.1073(3) 1.0943(2) 0.0249(8) Uani 1 1 d . . . . .
C45 C 0.0831(3) 0.1229(3) 1.1151(2) 0.0251(8) Uani 1 1 d . . . . .
C46 C 0.1533(3) 0.1757(3) 1.0541(2) 0.0249(8) Uani 1 1 d . . . . .
C47 C 0.2521(3) 0.1897(3) 1.0722(2) 0.0279(9) Uani 1 1 d . . . . .
C48 C 0.3530(4) 0.1192(4) 1.0484(4) 0.0509(13) Uani 1 1 d . . . . .
H48 H 0.3586 0.0588 1.0260 0.061 Uiso 1 1 calc R U . . .
C49 C 0.4467(4) 0.1376(5) 1.0575(4) 0.0616(15) Uani 1 1 d . . . . .
H49 H 0.5149 0.0901 1.0400 0.074 Uiso 1 1 calc R U . . .
C50 C 0.4398(4) 0.2249(4) 1.0918(3) 0.0536(13) Uani 1 1 d . . . . .
H50 H 0.5029 0.2376 1.0967 0.064 Uiso 1 1 calc R U . . .
C51 C 0.3388(4) 0.2933(4) 1.1190(3) 0.0447(11) Uani 1 1 d . . . . .
H51 H 0.3331 0.3514 1.1444 0.054 Uiso 1 1 calc R U . . .
C52 C 0.2456(4) 0.2764(3) 1.1090(3) 0.0358(10) Uani 1 1 d . . . . .
H52 H 0.1776 0.3238 1.1271 0.043 Uiso 1 1 calc R U . . .
C53 C 0.1045(3) 0.0791(3) 1.2035(2) 0.0248(8) Uani 1 1 d . . . . .
C54 C 0.1606(3) -0.0256(3) 1.2225(3) 0.0328(9) Uani 1 1 d . . . . .
H54 H 0.1837 -0.0704 1.1800 0.039 Uiso 1 1 calc R U . . .
C55 C 0.1831(3) -0.0649(3) 1.3037(3) 0.0358(10) Uani 1 1 d . . . . .
H55 H 0.2221 -0.1353 1.3152 0.043 Uiso 1 1 calc R U . . .
C56 C 0.1476(3) 0.0002(3) 1.3675(3) 0.0299(9) Uani 1 1 d . . . . .
H56 H 0.1611 -0.0266 1.4226 0.036 Uiso 1 1 calc R U . . .
C57 C 0.0931(3) 0.1032(4) 1.3501(3) 0.0360(10) Uani 1 1 d . . . . .
H57 H 0.0704 0.1472 1.3932 0.043 Uiso 1 1 calc R U . . .
C58 C 0.0706(3) 0.1440(3) 1.2684(3) 0.0333(9) Uani 1 1 d . . . . .
H58 H 0.0329 0.2149 1.2572 0.040 Uiso 1 1 calc R U . . .
C59 C 0.7012(4) 0.3672(3) 0.7632(3) 0.0381(11) Uani 1 1 d . . . . .
C60 C 0.6891(4) 0.4366(4) 1.0100(3) 0.0529(13) Uani 1 1 d . . . . .
H60A H 0.6455 0.5070 1.0231 0.063 Uiso 1 1 calc R U . . .
H60B H 0.6594 0.4164 0.9700 0.063 Uiso 1 1 calc R U . . .
N1 N 0.4700(2) 0.0696(2) 0.7035(2) 0.0247(7) Uani 1 1 d . . . . .
N2 N 0.3164(2) 0.1382(2) 0.66873(18) 0.0199(6) Uani 1 1 d . . . . .
N3 N 0.1885(2) 0.2659(2) 0.89529(19) 0.0242(7) Uani 1 1 d . . . . .
N4 N 0.0464(2) 0.1992(2) 0.94848(19) 0.0221(7) Uani 1 1 d . . . . .
O1 O 0.5153(3) 0.3856(3) 0.8793(2) 0.0637(10) Uani 1 1 d . . . . .
O2 O 0.5868(3) 0.2308(3) 0.8061(2) 0.0593(10) Uani 1 1 d . . . . .
O3 O 0.6740(3) 0.2507(3) 0.9092(2) 0.0599(10) Uani 1 1 d . . . . .
F1 F 0.7909(2) 0.3052(3) 0.7292(3) 0.0930(13) Uani 1 1 d . . . . .
F2 F 0.7166(3) 0.4479(2) 0.7877(2) 0.0620(8) Uani 1 1 d . . . . .
F3 F 0.6508(3) 0.4155(3) 0.69381(19) 0.0755(10) Uani 1 1 d . . . . .
S1 S 0.60737(9) 0.30178(9) 0.84913(8) 0.0396(3) Uani 1 1 d . . . . .
Rh1 Rh 0.19950(2) 0.34993(2) 0.70149(2) 0.01983(11) Uani 1 1 d . . . . .
Cl1 Cl 0.68041(14) 0.34727(11) 1.10621(9) 0.0697(4) Uani 1 1 d . . . . .
Cl2 Cl 0.82738(11) 0.43953(10) 0.95921(8) 0.0567(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 N1 1.347(5) . ?
C1 N2 1.347(5) . ?
C1 C12 1.438(5) . ?
C2 N1 1.482(5) . ?
C3 C4 1.365(5) . ?
C3 N1 1.398(5) . ?
C3 H3 0.9300 . ?
C4 N2 1.391(4) . ?
C4 Rh1 2.043(4) . ?
C5 N2 1.375(4) . ?
C5 C10 1.395(5) . ?
C5 C6 1.396(5) . ?
C6 C7 1.385(5) . ?
C6 Rh1 2.058(4) . ?
C7 C8 1.403(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.422(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.451(5) . ?
C11 C12 1.386(5) . ?
C11 C19 1.487(5) . ?
C12 C13 1.489(5) . ?
C13 C18 1.386(5) . ?
C13 C14 1.391(5) . ?
C14 C15 1.384(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.394(5) . ?
C19 C24 1.395(5) . ?
C20 C21 1.385(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.379(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.377(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.387(6) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C29 1.426(5) . ?
C25 C26 1.433(5) . ?
C25 C34 1.501(5) . ?
C25 Rh1 2.264(3) . ?
C26 C27 1.416(5) . ?
C26 C33 1.496(5) . ?
C26 Rh1 2.228(3) . ?
C27 C28 1.438(5) . ?
C27 C32 1.486(5) . ?
C27 Rh1 2.233(3) . ?
C28 C29 1.435(5) . ?
C28 C31 1.503(5) . ?
C28 Rh1 2.213(4) . ?
C29 C30 1.495(6) . ?
C29 Rh1 2.253(4) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 N4 1.360(5) . ?
C35 N3 1.360(5) . ?
C35 C46 1.430(5) . ?
C36 N3 1.478(5) . ?
C37 C38 1.362(5) . ?
C37 N3 1.414(5) . ?
C37 Rh1 2.028(4) . ?
C38 N4 1.387(5) . ?
C38 H38 0.9300 . ?
C39 C40 1.389(5) . ?
C39 N4 1.399(4) . ?
C39 C44 1.412(5) . ?
C40 C41 1.379(5) . ?
C40 H40 0.9300 . ?
C41 C42 1.400(6) . ?
C41 H41 0.9300 . ?
C42 C43 1.346(6) . ?
C42 H42 0.9300 . ?
C43 C44 1.409(5) . ?
C43 H43 0.9300 . ?
C44 C45 1.446(5) . ?
C45 C46 1.365(5) . ?
C45 C53 1.492(5) . ?
C46 C47 1.494(5) . ?
C47 C48 1.372(6) . ?
C47 C52 1.386(6) . ?
C48 C49 1.389(7) . ?
C48 H48 0.9300 . ?
C49 C50 1.367(7) . ?
C49 H49 0.9300 . ?
C50 C51 1.369(7) . ?
C50 H50 0.9300 . ?
C51 C52 1.379(6) . ?
C51 H51 0.9300 . ?
C52 H52 0.9300 . ?
C53 C54 1.382(6) . ?
C53 C58 1.388(5) . ?
C54 C55 1.381(6) . ?
C54 H54 0.9300 . ?
C55 C56 1.375(6) . ?
C55 H55 0.9300 . ?
C56 C57 1.353(6) . ?
C56 H56 0.9300 . ?
C57 C58 1.392(6) . ?
C57 H57 0.9300 . ?
C58 H58 0.9300 . ?
C59 F1 1.261(5) . ?
C59 F2 1.319(5) . ?
C59 F3 1.405(6) . ?
C59 S1 1.818(4) . ?
C60 Cl1 1.731(5) . ?
C60 Cl2 1.768(5) . ?
C60 H60A 0.9700 . ?
C60 H60B 0.9700 . ?
O1 S1 1.418(3) . ?
O2 S1 1.423(3) . ?
O3 S1 1.425(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
N1 C1 N2 105.2(3) . . ?
N1 C1 C12 135.9(3) . . ?
N2 C1 C12 118.9(3) . . ?
C4 C3 N1 110.2(3) . . ?
C4 C3 H3 124.9 . . ?
N1 C3 H3 124.9 . . ?
C3 C4 N2 102.1(3) . . ?
C3 C4 Rh1 146.6(3) . . ?
N2 C4 Rh1 111.1(2) . . ?
N2 C5 C10 117.8(3) . . ?
N2 C5 C6 114.0(3) . . ?
C10 C5 C6 128.2(3) . . ?
C7 C6 C5 113.8(3) . . ?
C7 C6 Rh1 132.4(3) . . ?
C5 C6 Rh1 113.8(2) . . ?
C6 C7 C8 121.4(3) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 122.6(3) . . ?
C9 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
C8 C9 C10 119.1(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C5 C10 C9 114.9(3) . . ?
C5 C10 C11 118.8(3) . . ?
C9 C10 C11 126.3(3) . . ?
C12 C11 C10 121.3(3) . . ?
C12 C11 C19 120.2(3) . . ?
C10 C11 C19 118.5(3) . . ?
C11 C12 C1 117.8(3) . . ?
C11 C12 C13 123.4(3) . . ?
C1 C12 C13 118.8(3) . . ?
C18 C13 C14 118.7(3) . . ?
C18 C13 C12 120.1(3) . . ?
C14 C13 C12 121.1(3) . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.6(4) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 120.3(4) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 119.8(4) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C13 121.0(3) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
C20 C19 C24 117.9(3) . . ?
C20 C19 C11 120.8(3) . . ?
C24 C19 C11 121.2(3) . . ?
C21 C20 C19 121.0(3) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C20 120.2(4) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 119.7(4) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 120.4(4) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C19 120.8(4) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
C29 C25 C26 107.9(3) . . ?
C29 C25 C34 127.6(4) . . ?
C26 C25 C34 123.9(4) . . ?
C29 C25 Rh1 71.2(2) . . ?
C26 C25 Rh1 70.06(19) . . ?
C34 C25 Rh1 131.1(3) . . ?
C27 C26 C25 108.0(3) . . ?
C27 C26 C33 126.5(3) . . ?
C25 C26 C33 125.3(3) . . ?
C27 C26 Rh1 71.66(19) . . ?
C25 C26 Rh1 72.7(2) . . ?
C33 C26 Rh1 125.0(3) . . ?
C26 C27 C28 108.6(3) . . ?
C26 C27 C32 125.5(3) . . ?
C28 C27 C32 125.7(3) . . ?
C26 C27 Rh1 71.3(2) . . ?
C28 C27 Rh1 70.4(2) . . ?
C32 C27 Rh1 128.4(3) . . ?
C29 C28 C27 107.0(3) . . ?
C29 C28 C31 126.4(3) . . ?
C27 C28 C31 125.9(3) . . ?
C29 C28 Rh1 72.8(2) . . ?
C27 C28 Rh1 71.9(2) . . ?
C31 C28 Rh1 128.0(3) . . ?
C25 C29 C28 108.3(3) . . ?
C25 C29 C30 126.7(4) . . ?
C28 C29 C30 124.9(4) . . ?
C25 C29 Rh1 72.0(2) . . ?
C28 C29 Rh1 69.8(2) . . ?
C30 C29 Rh1 126.8(3) . . ?
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 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C27 C32 H32A 109.5 . . ?
C27 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C27 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C26 C33 H33A 109.5 . . ?
C26 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C26 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C25 C34 H34A 109.5 . . ?
C25 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C25 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N4 C35 N3 106.8(3) . . ?
N4 C35 C46 121.7(3) . . ?
N3 C35 C46 131.4(3) . . ?
C38 C37 N3 104.5(3) . . ?
C38 C37 Rh1 131.7(3) . . ?
N3 C37 Rh1 123.8(2) . . ?
C37 C38 N4 109.7(3) . . ?
C37 C38 H38 125.2 . . ?
N4 C38 H38 125.2 . . ?
C40 C39 N4 120.9(3) . . ?
C40 C39 C44 121.2(3) . . ?
N4 C39 C44 117.9(3) . . ?
C41 C40 C39 119.8(4) . . ?
C41 C40 H40 120.1 . . ?
C39 C40 H40 120.1 . . ?
C40 C41 C42 119.4(4) . . ?
C40 C41 H41 120.3 . . ?
C42 C41 H41 120.3 . . ?
C43 C42 C41 120.8(4) . . ?
C43 C42 H42 119.6 . . ?
C41 C42 H42 119.6 . . ?
C42 C43 C44 121.9(4) . . ?
C42 C43 H43 119.0 . . ?
C44 C43 H43 119.0 . . ?
C43 C44 C39 116.7(3) . . ?
C43 C44 C45 123.5(3) . . ?
C39 C44 C45 119.8(3) . . ?
C46 C45 C44 120.9(3) . . ?
C46 C45 C53 119.1(3) . . ?
C44 C45 C53 120.0(3) . . ?
C45 C46 C35 117.9(3) . . ?
C45 C46 C47 122.3(3) . . ?
C35 C46 C47 119.8(3) . . ?
C48 C47 C52 118.4(4) . . ?
C48 C47 C46 120.3(4) . . ?
C52 C47 C46 121.2(4) . . ?
C47 C48 C49 120.4(5) . . ?
C47 C48 H48 119.8 . . ?
C49 C48 H48 119.8 . . ?
C50 C49 C48 120.7(5) . . ?
C50 C49 H49 119.7 . . ?
C48 C49 H49 119.7 . . ?
C49 C50 C51 119.3(4) . . ?
C49 C50 H50 120.3 . . ?
C51 C50 H50 120.3 . . ?
C50 C51 C52 120.4(5) . . ?
C50 C51 H51 119.8 . . ?
C52 C51 H51 119.8 . . ?
C51 C52 C47 120.8(4) . . ?
C51 C52 H52 119.6 . . ?
C47 C52 H52 119.6 . . ?
C54 C53 C58 118.2(4) . . ?
C54 C53 C45 121.3(3) . . ?
C58 C53 C45 120.5(3) . . ?
C55 C54 C53 121.1(4) . . ?
C55 C54 H54 119.5 . . ?
C53 C54 H54 119.5 . . ?
C56 C55 C54 119.9(4) . . ?
C56 C55 H55 120.1 . . ?
C54 C55 H55 120.1 . . ?
C57 C56 C55 120.1(4) . . ?
C57 C56 H56 120.0 . . ?
C55 C56 H56 120.0 . . ?
C56 C57 C58 120.6(4) . . ?
C56 C57 H57 119.7 . . ?
C58 C57 H57 119.7 . . ?
C53 C58 C57 120.2(4) . . ?
C53 C58 H58 119.9 . . ?
C57 C58 H58 119.9 . . ?
F1 C59 F2 112.0(4) . . ?
F1 C59 F3 105.3(4) . . ?
F2 C59 F3 103.3(4) . . ?
F1 C59 S1 114.4(3) . . ?
F2 C59 S1 112.6(3) . . ?
F3 C59 S1 108.2(3) . . ?
Cl1 C60 Cl2 110.7(3) . . ?
Cl1 C60 H60A 109.5 . . ?
Cl2 C60 H60A 109.5 . . ?
Cl1 C60 H60B 109.5 . . ?
Cl2 C60 H60B 109.5 . . ?
H60A C60 H60B 108.1 . . ?
C1 N1 C3 108.5(3) . . ?
C1 N1 C2 128.5(3) . . ?
C3 N1 C2 122.9(3) . . ?
C1 N2 C5 125.3(3) . . ?
C1 N2 C4 114.0(3) . . ?
C5 N2 C4 120.6(3) . . ?
C35 N3 C37 110.4(3) . . ?
C35 N3 C36 125.6(3) . . ?
C37 N3 C36 124.0(3) . . ?
C35 N4 C38 108.6(3) . . ?
C35 N4 C39 121.8(3) . . ?
C38 N4 C39 129.6(3) . . ?
O1 S1 O2 115.5(2) . . ?
O1 S1 O3 115.2(2) . . ?
O2 S1 O3 114.2(2) . . ?
O1 S1 C59 104.8(2) . . ?
O2 S1 C59 104.1(2) . . ?
O3 S1 C59 100.7(2) . . ?
C37 Rh1 C4 85.09(14) . . ?
C37 Rh1 C6 88.04(14) . . ?
C4 Rh1 C6 80.57(14) . . ?
C37 Rh1 C28 109.35(14) . . ?
C4 Rh1 C28 163.66(13) . . ?
C6 Rh1 C28 106.83(14) . . ?
C37 Rh1 C26 155.49(14) . . ?
C4 Rh1 C26 100.78(13) . . ?
C6 Rh1 C26 116.32(13) . . ?
C28 Rh1 C26 62.91(13) . . ?
C37 Rh1 C27 145.97(14) . . ?
C4 Rh1 C27 128.83(13) . . ?
C6 Rh1 C27 94.45(13) . . ?
C28 Rh1 C27 37.74(13) . . ?
C26 Rh1 C27 37.00(13) . . ?
C37 Rh1 C29 97.12(14) . . ?
C4 Rh1 C29 135.85(14) . . ?
C6 Rh1 C29 143.42(14) . . ?
C28 Rh1 C29 37.47(14) . . ?
C26 Rh1 C29 62.09(14) . . ?
C27 Rh1 C29 61.97(14) . . ?
C37 Rh1 C25 118.31(14) . . ?
C4 Rh1 C25 104.44(14) . . ?
C6 Rh1 C25 153.31(14) . . ?
C28 Rh1 C25 62.41(13) . . ?
C26 Rh1 C25 37.20(14) . . ?
C27 Rh1 C25 61.67(13) . . ?
C29 Rh1 C25 36.81(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
N1 C3 C4 N2 0.4(4) . . . . ?
N1 C3 C4 Rh1 174.0(4) . . . . ?
N2 C5 C6 C7 179.8(3) . . . . ?
C10 C5 C6 C7 -0.3(5) . . . . ?
N2 C5 C6 Rh1 0.5(4) . . . . ?
C10 C5 C6 Rh1 -179.6(3) . . . . ?
C5 C6 C7 C8 -1.3(5) . . . . ?
Rh1 C6 C7 C8 177.8(3) . . . . ?
C6 C7 C8 C9 1.7(6) . . . . ?
C7 C8 C9 C10 -0.5(5) . . . . ?
N2 C5 C10 C9 -178.6(3) . . . . ?
C6 C5 C10 C9 1.5(5) . . . . ?
N2 C5 C10 C11 0.9(5) . . . . ?
C6 C5 C10 C11 -179.1(3) . . . . ?
C8 C9 C10 C5 -1.0(5) . . . . ?
C8 C9 C10 C11 179.6(3) . . . . ?
C5 C10 C11 C12 1.0(5) . . . . ?
C9 C10 C11 C12 -179.6(3) . . . . ?
C5 C10 C11 C19 -177.2(3) . . . . ?
C9 C10 C11 C19 2.2(5) . . . . ?
C10 C11 C12 C1 -0.3(5) . . . . ?
C19 C11 C12 C1 177.9(3) . . . . ?
C10 C11 C12 C13 177.2(3) . . . . ?
C19 C11 C12 C13 -4.6(5) . . . . ?
N1 C1 C12 C11 176.5(4) . . . . ?
N2 C1 C12 C11 -2.3(5) . . . . ?
N1 C1 C12 C13 -1.1(6) . . . . ?
N2 C1 C12 C13 -179.9(3) . . . . ?
C11 C12 C13 C18 -69.8(5) . . . . ?
C1 C12 C13 C18 107.6(4) . . . . ?
C11 C12 C13 C14 113.8(4) . . . . ?
C1 C12 C13 C14 -68.8(5) . . . . ?
C18 C13 C14 C15 -3.0(6) . . . . ?
C12 C13 C14 C15 173.4(4) . . . . ?
C13 C14 C15 C16 1.0(6) . . . . ?
C14 C15 C16 C17 1.9(6) . . . . ?
C15 C16 C17 C18 -2.7(6) . . . . ?
C16 C17 C18 C13 0.6(6) . . . . ?
C14 C13 C18 C17 2.2(6) . . . . ?
C12 C13 C18 C17 -174.3(4) . . . . ?
C12 C11 C19 C20 -64.4(5) . . . . ?
C10 C11 C19 C20 113.9(4) . . . . ?
C12 C11 C19 C24 119.6(4) . . . . ?
C10 C11 C19 C24 -62.1(5) . . . . ?
C24 C19 C20 C21 2.1(6) . . . . ?
C11 C19 C20 C21 -174.0(3) . . . . ?
C19 C20 C21 C22 -1.2(6) . . . . ?
C20 C21 C22 C23 -0.8(6) . . . . ?
C21 C22 C23 C24 1.7(6) . . . . ?
C22 C23 C24 C19 -0.7(6) . . . . ?
C20 C19 C24 C23 -1.2(6) . . . . ?
C11 C19 C24 C23 174.9(4) . . . . ?
C29 C25 C26 C27 1.9(4) . . . . ?
C34 C25 C26 C27 -169.8(3) . . . . ?
Rh1 C25 C26 C27 63.4(2) . . . . ?
C29 C25 C26 C33 177.5(3) . . . . ?
C34 C25 C26 C33 5.8(6) . . . . ?
Rh1 C25 C26 C33 -121.0(4) . . . . ?
C29 C25 C26 Rh1 -61.5(3) . . . . ?
C34 C25 C26 Rh1 126.8(4) . . . . ?
C25 C26 C27 C28 -3.3(4) . . . . ?
C33 C26 C27 C28 -178.8(3) . . . . ?
Rh1 C26 C27 C28 60.8(2) . . . . ?
C25 C26 C27 C32 171.5(3) . . . . ?
C33 C26 C27 C32 -3.9(6) . . . . ?
Rh1 C26 C27 C32 -124.3(4) . . . . ?
C25 C26 C27 Rh1 -64.1(2) . . . . ?
C33 C26 C27 Rh1 120.4(4) . . . . ?
C26 C27 C28 C29 3.4(4) . . . . ?
C32 C27 C28 C29 -171.4(3) . . . . ?
Rh1 C27 C28 C29 64.8(2) . . . . ?
C26 C27 C28 C31 174.3(3) . . . . ?
C32 C27 C28 C31 -0.5(6) . . . . ?
Rh1 C27 C28 C31 -124.3(4) . . . . ?
C26 C27 C28 Rh1 -61.4(2) . . . . ?
C32 C27 C28 Rh1 123.8(4) . . . . ?
C26 C25 C29 C28 0.2(4) . . . . ?
C34 C25 C29 C28 171.5(4) . . . . ?
Rh1 C25 C29 C28 -60.6(2) . . . . ?
C26 C25 C29 C30 -176.3(4) . . . . ?
C34 C25 C29 C30 -5.0(6) . . . . ?
Rh1 C25 C29 C30 122.9(4) . . . . ?
C26 C25 C29 Rh1 60.8(2) . . . . ?
C34 C25 C29 Rh1 -127.9(4) . . . . ?
C27 C28 C29 C25 -2.2(4) . . . . ?
C31 C28 C29 C25 -173.1(3) . . . . ?
Rh1 C28 C29 C25 62.0(3) . . . . ?
C27 C28 C29 C30 174.4(4) . . . . ?
C31 C28 C29 C30 3.5(6) . . . . ?
Rh1 C28 C29 C30 -121.4(4) . . . . ?
C27 C28 C29 Rh1 -64.2(2) . . . . ?
C31 C28 C29 Rh1 124.9(4) . . . . ?
N3 C37 C38 N4 -0.7(4) . . . . ?
Rh1 C37 C38 N4 177.2(3) . . . . ?
N4 C39 C40 C41 179.0(3) . . . . ?
C44 C39 C40 C41 -1.9(6) . . . . ?
C39 C40 C41 C42 -0.2(6) . . . . ?
C40 C41 C42 C43 1.4(6) . . . . ?
C41 C42 C43 C44 -0.6(6) . . . . ?
C42 C43 C44 C39 -1.3(6) . . . . ?
C42 C43 C44 C45 179.6(4) . . . . ?
C40 C39 C44 C43 2.5(5) . . . . ?
N4 C39 C44 C43 -178.3(3) . . . . ?
C40 C39 C44 C45 -178.3(3) . . . . ?
N4 C39 C44 C45 0.9(5) . . . . ?
C43 C44 C45 C46 179.2(4) . . . . ?
C39 C44 C45 C46 0.1(5) . . . . ?
C43 C44 C45 C53 0.5(6) . . . . ?
C39 C44 C45 C53 -178.6(3) . . . . ?
C44 C45 C46 C35 -0.4(5) . . . . ?
C53 C45 C46 C35 178.3(3) . . . . ?
C44 C45 C46 C47 -177.7(3) . . . . ?
C53 C45 C46 C47 1.0(5) . . . . ?
N4 C35 C46 C45 -0.3(5) . . . . ?
N3 C35 C46 C45 -177.8(4) . . . . ?
N4 C35 C46 C47 177.1(3) . . . . ?
N3 C35 C46 C47 -0.4(6) . . . . ?
C45 C46 C47 C48 94.3(5) . . . . ?
C35 C46 C47 C48 -82.9(5) . . . . ?
C45 C46 C47 C52 -89.1(5) . . . . ?
C35 C46 C47 C52 93.7(5) . . . . ?
C52 C47 C48 C49 -2.8(7) . . . . ?
C46 C47 C48 C49 173.8(5) . . . . ?
C47 C48 C49 C50 1.3(9) . . . . ?
C48 C49 C50 C51 1.3(8) . . . . ?
C49 C50 C51 C52 -2.3(7) . . . . ?
C50 C51 C52 C47 0.7(7) . . . . ?
C48 C47 C52 C51 1.9(6) . . . . ?
C46 C47 C52 C51 -174.7(4) . . . . ?
C46 C45 C53 C54 -95.9(5) . . . . ?
C44 C45 C53 C54 82.8(5) . . . . ?
C46 C45 C53 C58 82.3(5) . . . . ?
C44 C45 C53 C58 -99.0(4) . . . . ?
C58 C53 C54 C55 -0.3(6) . . . . ?
C45 C53 C54 C55 178.0(4) . . . . ?
C53 C54 C55 C56 1.1(6) . . . . ?
C54 C55 C56 C57 -1.5(6) . . . . ?
C55 C56 C57 C58 1.1(6) . . . . ?
C54 C53 C58 C57 -0.2(6) . . . . ?
C45 C53 C58 C57 -178.5(4) . . . . ?
C56 C57 C58 C53 -0.2(6) . . . . ?
N2 C1 N1 C3 -0.9(4) . . . . ?
C12 C1 N1 C3 -179.9(4) . . . . ?
N2 C1 N1 C2 177.4(3) . . . . ?
C12 C1 N1 C2 -1.5(7) . . . . ?
C4 C3 N1 C1 0.3(4) . . . . ?
C4 C3 N1 C2 -178.2(3) . . . . ?
N1 C1 N2 C5 -174.6(3) . . . . ?
C12 C1 N2 C5 4.5(5) . . . . ?
N1 C1 N2 C4 1.3(4) . . . . ?
C12 C1 N2 C4 -179.6(3) . . . . ?
C10 C5 N2 C1 -3.8(5) . . . . ?
C6 C5 N2 C1 176.2(3) . . . . ?
C10 C5 N2 C4 -179.4(3) . . . . ?
C6 C5 N2 C4 0.5(4) . . . . ?
C3 C4 N2 C1 -1.1(4) . . . . ?
Rh1 C4 N2 C1 -177.3(2) . . . . ?
C3 C4 N2 C5 175.0(3) . . . . ?
Rh1 C4 N2 C5 -1.2(4) . . . . ?
N4 C35 N3 C37 -1.3(4) . . . . ?
C46 C35 N3 C37 176.5(4) . . . . ?
N4 C35 N3 C36 176.1(3) . . . . ?
C46 C35 N3 C36 -6.1(6) . . . . ?
C38 C37 N3 C35 1.2(4) . . . . ?
Rh1 C37 N3 C35 -176.9(3) . . . . ?
C38 C37 N3 C36 -176.2(3) . . . . ?
Rh1 C37 N3 C36 5.7(5) . . . . ?
N3 C35 N4 C38 0.8(4) . . . . ?
C46 C35 N4 C38 -177.2(3) . . . . ?
N3 C35 N4 C39 179.3(3) . . . . ?
C46 C35 N4 C39 1.3(5) . . . . ?
C37 C38 N4 C35 0.0(4) . . . . ?
C37 C38 N4 C39 -178.4(3) . . . . ?
C40 C39 N4 C35 177.6(3) . . . . ?
C44 C39 N4 C35 -1.5(5) . . . . ?
C40 C39 N4 C38 -4.2(6) . . . . ?
C44 C39 N4 C38 176.6(3) . . . . ?
F1 C59 S1 O1 178.1(4) . . . . ?
F2 C59 S1 O1 48.7(4) . . . . ?
F3 C59 S1 O1 -64.8(3) . . . . ?
F1 C59 S1 O2 -60.2(4) . . . . ?
F2 C59 S1 O2 170.3(3) . . . . ?
F3 C59 S1 O2 56.8(3) . . . . ?
F1 C59 S1 O3 58.3(4) . . . . ?
F2 C59 S1 O3 -71.2(4) . . . . ?
F3 C59 S1 O3 175.3(3) . . . . ?

_refine_diff_density_max         0.832
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.086

_shelxl_version_number           2014-3



