# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_asme3
_database_code_depnum_ccdc_archive 'CCDC 1813579'

_audit_update_record             
;
2017-12-27 deposited with the CCDC.
2018-04-09 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C58 H52 F4 I2 N4 O8 S2'
_chemical_formula_weight         1326.99
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'
I I -0.4742 1.8119 '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                   8.1917(4)
_cell_length_b                   9.5688(5)
_cell_length_c                   18.0523(10)
_cell_angle_alpha                100.6726(9)
_cell_angle_beta                 91.6388(9)
_cell_angle_gamma                104.9351(9)
_cell_volume                     1339.22(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9912
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.69

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_F_000             666
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.026
_exptl_crystal_size_min          0.023
_exptl_absorpt_coefficient_mu    1.327
_shelx_estimated_absorpt_T_min   0.730
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.8410
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_process_details   analytical
_exptl_absorpt_special_details   
'based on measured indexed crystal faces, Bruker SHELXTL2014 (Sheldrick, 2014)'


_diffrn_ambient_temperature      100(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            31002
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.152
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6157
_reflns_number_gt                5049
_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 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker Apex2 SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_structure_refinement  'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_molecular_graphics    'XP in SHELXTL-plus, Bruker 2014'
_computing_publication_material  'SHELXL2014/7, Sheldrick, G. M. 2014'


_refine_special_details          
;
All H atoms were positioned geometrically ( C---H = 0.93/1.00 Å) and   
allowed to ride with Uiso(H)= 1.2/1.5Ueq(C).
Methyl ones were allowed to rotate around the corresponding C---C.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0254P)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         6157
_refine_ls_number_parameters     352
_refine_ls_number_restraints     303
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0525
_refine_ls_wR_factor_gt          0.0499
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.946
_refine_ls_shift/su_max          0.004
_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
I1 I -0.13889(2) 0.61487(2) 0.62939(2) 0.02124(5) Uani 1 1 d . U . . .
F2 F -0.21165(16) 0.67891(15) 0.46343(7) 0.0287(3) Uani 1 1 d . U . . .
F3 F -0.48745(16) 0.59726(15) 0.36797(7) 0.0256(3) Uani 1 1 d . U . . .
O1 O 1.43906(19) 0.27187(18) 0.88396(9) 0.0264(4) Uani 1 1 d . U . . .
O2 O 1.1205(2) 0.11894(18) 0.82473(10) 0.0364(5) Uani 1 1 d . U . . .
O3 O 0.97696(17) 0.27931(16) 0.80038(8) 0.0183(3) Uani 1 1 d . U . . .
O31 O 0.4547(2) -0.0244(2) 0.61509(13) 0.0604(7) Uani 1 1 d . U . . .
S1 S 0.73364(6) 0.64590(6) 0.85011(3) 0.01517(11) Uani 1 1 d . U . . .
N1 N 1.2040(2) 0.36128(18) 0.88485(9) 0.0136(4) Uani 1 1 d . U . . .
N2 N 0.1418(2) 0.6824(2) 0.73318(10) 0.0208(4) Uani 1 1 d . U . . .
C1 C 1.3662(3) 0.3596(2) 0.91230(11) 0.0155(4) Uani 1 1 d . U . . .
C2 C 1.4260(2) 0.4893(2) 0.97766(11) 0.0123(4) Uani 1 1 d . U . . .
C3 C 1.2972(2) 0.5716(2) 0.97792(11) 0.0119(4) Uani 1 1 d . U . . .
C4 C 1.2794(2) 0.7057(2) 1.01917(12) 0.0141(4) Uani 1 1 d . U . . .
H4A H 1.3636 0.7624 1.0581 0.017 Uiso 1 1 calc R U . . .
C5 C 1.1406(2) 0.7562(2) 1.00373(12) 0.0141(4) Uani 1 1 d . U . . .
H5A H 1.1313 0.8472 1.0324 0.017 Uiso 1 1 calc R U . . .
C6 C 1.0140(2) 0.6764(2) 0.94694(11) 0.0123(4) Uani 1 1 d . U . . .
C7 C 1.0292(2) 0.5426(2) 0.90496(11) 0.0132(4) Uani 1 1 d . U . . .
H7A H 0.9451 0.4864 0.8658 0.016 Uiso 1 1 calc R U . . .
C8 C 1.1672(2) 0.4932(2) 0.92100(11) 0.0123(4) Uani 1 1 d . U . . .
C9 C 0.8654(2) 0.7297(2) 0.93121(11) 0.0128(4) Uani 1 1 d . U . . .
C10 C 0.8066(2) 0.8367(2) 0.97388(12) 0.0152(4) Uani 1 1 d . U . . .
H10A H 0.8624 0.8956 1.0204 0.018 Uiso 1 1 calc R U . . .
C11 C 0.6537(3) 0.8508(2) 0.94161(11) 0.0153(4) Uani 1 1 d . U . . .
H11A H 0.5964 0.9204 0.9642 0.018 Uiso 1 1 calc R U . . .
C12 C 0.5964(2) 0.7535(2) 0.87417(12) 0.0141(4) Uani 1 1 d . U . . .
C13 C 0.4410(2) 0.7308(2) 0.82588(11) 0.0143(4) Uani 1 1 d . U . . .
C14 C 0.3807(3) 0.6033(2) 0.77037(12) 0.0185(5) Uani 1 1 d . U . . .
H14A H 0.4407 0.5297 0.7631 0.022 Uiso 1 1 calc R U . . .
C15 C 0.2336(3) 0.5843(3) 0.72612(12) 0.0207(5) Uani 1 1 d . U . . .
H15A H 0.1954 0.4967 0.6885 0.025 Uiso 1 1 calc R U . . .
C16 C 0.1990(3) 0.8047(2) 0.78642(12) 0.0197(5) Uani 1 1 d . U . . .
H16A H 0.1355 0.8758 0.7925 0.024 Uiso 1 1 calc R U . . .
C17 C 0.3460(3) 0.8336(2) 0.83329(12) 0.0171(5) Uani 1 1 d . U . . .
H17A H 0.3816 0.9226 0.8701 0.021 Uiso 1 1 calc R U . . .
C18 C 1.0984(3) 0.2394(2) 0.83357(12) 0.0190(5) Uani 1 1 d . U . . .
C19 C 0.8414(3) 0.1693(2) 0.74594(12) 0.0197(5) Uani 1 1 d . U . . .
C20 C 0.7524(3) 0.0430(3) 0.78194(14) 0.0288(6) Uani 1 1 d . U . . .
H20A H 0.6647 -0.0273 0.7455 0.043 Uiso 1 1 calc R U . . .
H20B H 0.8347 -0.0069 0.7970 0.043 Uiso 1 1 calc R U . . .
H20C H 0.6999 0.0811 0.8266 0.043 Uiso 1 1 calc R U . . .
C21 C 0.9207(3) 0.1195(3) 0.67510(13) 0.0347(6) Uani 1 1 d . U . . .
H21A H 0.8338 0.0476 0.6390 0.052 Uiso 1 1 calc R U . . .
H21B H 0.9708 0.2049 0.6526 0.052 Uiso 1 1 calc R U . . .
H21C H 1.0092 0.0737 0.6876 0.052 Uiso 1 1 calc R U . . .
C22 C 0.7230(3) 0.2608(3) 0.73258(14) 0.0304(6) Uani 1 1 d . U . . .
H22A H 0.6272 0.2000 0.6972 0.046 Uiso 1 1 calc R U . . .
H22B H 0.6810 0.2973 0.7807 0.046 Uiso 1 1 calc R U . . .
H22C H 0.7838 0.3446 0.7112 0.046 Uiso 1 1 calc R U . . .
C32 C 0.4238(4) -0.1662(3) 0.57141(19) 0.0541(9) Uani 1 1 d . U . . .
H32A H 0.3937 -0.2407 0.6037 0.065 Uiso 1 1 calc R U . . .
H32B H 0.5260 -0.1784 0.5458 0.065 Uiso 1 1 calc R U . . .
C33 C 0.2784(4) -0.1854(3) 0.51362(17) 0.0465(8) Uani 1 1 d . U . . .
H33A H 0.1930 -0.2810 0.5109 0.056 Uiso 1 1 calc R U . . .
H33B H 0.3192 -0.1803 0.4628 0.056 Uiso 1 1 calc R U . . .
C34 C 0.2049(4) -0.0570(3) 0.54281(16) 0.0420(7) Uani 1 1 d . U . . .
H34A H 0.2266 0.0158 0.5093 0.050 Uiso 1 1 calc R U . . .
H34B H 0.0813 -0.0918 0.5465 0.050 Uiso 1 1 calc R U . . .
C35 C 0.2965(3) 0.0087(3) 0.61948(16) 0.0385(7) Uani 1 1 d . U . . .
H35A H 0.3121 0.1168 0.6315 0.046 Uiso 1 1 calc R U . . .
H35B H 0.2326 -0.0355 0.6589 0.046 Uiso 1 1 calc R U . . .
C41 C -0.3532(3) 0.5451(2) 0.55135(12) 0.0194(5) Uani 1 1 d . U . . .
C42 C -0.3533(3) 0.5896(2) 0.48287(12) 0.0198(5) Uani 1 1 d . U . . .
C43 C -0.4962(3) 0.5465(2) 0.43310(12) 0.0196(5) Uani 1 1 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
I1 C41 2.102(2) . ?
I1 N2 2.7845(17) . ?
F2 C42 1.350(3) . ?
F3 C43 1.350(2) . ?
O1 C1 1.199(2) . ?
O2 C18 1.195(3) . ?
O3 C18 1.319(2) . ?
O3 C19 1.503(2) . ?
O31 C32 1.394(3) . ?
O31 C35 1.412(3) . ?
S1 C12 1.723(2) . ?
S1 C9 1.726(2) . ?
N1 C1 1.410(2) . ?
N1 C18 1.414(3) . ?
N1 C8 1.418(3) . ?
N2 C16 1.337(3) . ?
N2 C15 1.337(3) . ?
C1 C2 1.511(3) . ?
C2 C2 1.384(4) 2_867 ?
C2 C3 1.470(3) . ?
C3 C4 1.404(3) . ?
C3 C8 1.412(3) . ?
C4 C5 1.385(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.397(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.399(3) . ?
C6 C9 1.476(3) . ?
C7 C8 1.376(3) . ?
C7 H7A 0.9500 . ?
C9 C10 1.363(3) . ?
C10 C11 1.414(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.375(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.467(3) . ?
C13 C17 1.394(3) . ?
C13 C14 1.395(3) . ?
C14 C15 1.379(3) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 C17 1.388(3) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C19 C21 1.505(3) . ?
C19 C22 1.506(3) . ?
C19 C20 1.510(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C32 C33 1.512(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.519(4) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.500(4) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C41 C42 1.380(3) . ?
C41 C43 1.386(3) 2_466 ?
C42 C43 1.379(3) . ?
C43 C41 1.386(3) 2_466 ?

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
C41 I1 N2 175.19(7) . . ?
C18 O3 C19 121.51(16) . . ?
C32 O31 C35 106.5(2) . . ?
C12 S1 C9 92.24(10) . . ?
C1 N1 C18 121.49(17) . . ?
C1 N1 C8 109.42(15) . . ?
C18 N1 C8 128.91(16) . . ?
C16 N2 C15 116.80(18) . . ?
C16 N2 I1 127.25(13) . . ?
C15 N2 I1 115.86(14) . . ?
O1 C1 N1 123.34(18) . . ?
O1 C1 C2 129.38(18) . . ?
N1 C1 C2 107.20(16) . . ?
C2 C2 C3 133.4(2) 2_867 . ?
C2 C2 C1 121.9(2) 2_867 . ?
C3 C2 C1 104.78(15) . . ?
C4 C3 C8 116.47(17) . . ?
C4 C3 C2 134.99(18) . . ?
C8 C3 C2 108.51(17) . . ?
C5 C4 C3 120.77(18) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 121.53(19) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C5 C6 C7 118.73(18) . . ?
C5 C6 C9 121.39(18) . . ?
C7 C6 C9 119.88(17) . . ?
C8 C7 C6 119.23(18) . . ?
C8 C7 H7A 120.4 . . ?
C6 C7 H7A 120.4 . . ?
C7 C8 C3 123.26(18) . . ?
C7 C8 N1 127.25(17) . . ?
C3 C8 N1 109.48(16) . . ?
C10 C9 C6 129.50(18) . . ?
C10 C9 S1 111.11(14) . . ?
C6 C9 S1 119.33(15) . . ?
C9 C10 C11 112.93(18) . . ?
C9 C10 H10A 123.5 . . ?
C11 C10 H10A 123.5 . . ?
C12 C11 C10 113.18(19) . . ?
C12 C11 H11A 123.4 . . ?
C10 C11 H11A 123.4 . . ?
C11 C12 C13 129.14(19) . . ?
C11 C12 S1 110.53(14) . . ?
C13 C12 S1 120.30(15) . . ?
C17 C13 C14 116.83(18) . . ?
C17 C13 C12 122.20(18) . . ?
C14 C13 C12 120.96(18) . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
N2 C15 C14 123.6(2) . . ?
N2 C15 H15A 118.2 . . ?
C14 C15 H15A 118.2 . . ?
N2 C16 C17 123.6(2) . . ?
N2 C16 H16A 118.2 . . ?
C17 C16 H16A 118.2 . . ?
C16 C17 C13 119.3(2) . . ?
C16 C17 H17A 120.3 . . ?
C13 C17 H17A 120.3 . . ?
O2 C18 O3 127.3(2) . . ?
O2 C18 N1 122.25(19) . . ?
O3 C18 N1 110.40(17) . . ?
O3 C19 C21 108.50(17) . . ?
O3 C19 C22 101.65(16) . . ?
C21 C19 C22 112.0(2) . . ?
O3 C19 C20 110.83(17) . . ?
C21 C19 C20 112.9(2) . . ?
C22 C19 C20 110.4(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O31 C32 C33 107.1(2) . . ?
O31 C32 H32A 110.3 . . ?
C33 C32 H32A 110.3 . . ?
O31 C32 H32B 110.3 . . ?
C33 C32 H32B 110.3 . . ?
H32A C32 H32B 108.5 . . ?
C32 C33 C34 103.7(2) . . ?
C32 C33 H33A 111.0 . . ?
C34 C33 H33A 111.0 . . ?
C32 C33 H33B 111.0 . . ?
C34 C33 H33B 111.0 . . ?
H33A C33 H33B 109.0 . . ?
C35 C34 C33 103.9(2) . . ?
C35 C34 H34A 111.0 . . ?
C33 C34 H34A 111.0 . . ?
C35 C34 H34B 111.0 . . ?
C33 C34 H34B 111.0 . . ?
H34A C34 H34B 109.0 . . ?
O31 C35 C34 105.2(2) . . ?
O31 C35 H35A 110.7 . . ?
C34 C35 H35A 110.7 . . ?
O31 C35 H35B 110.7 . . ?
C34 C35 H35B 110.7 . . ?
H35A C35 H35B 108.8 . . ?
C42 C41 C43 116.40(19) . 2_466 ?
C42 C41 I1 122.22(17) . . ?
C43 C41 I1 121.37(16) 2_466 . ?
F2 C42 C43 118.22(19) . . ?
F2 C42 C41 120.11(19) . . ?
C43 C42 C41 121.7(2) . . ?
F3 C43 C42 118.2(2) . . ?
F3 C43 C41 119.86(18) . 2_466 ?
C42 C43 C41 121.9(2) . 2_466 ?

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
C7 H7A O3 0.95 2.19 2.780(2) 119.0 .
C14 H14A F3 0.95 2.54 3.146(3) 121.9 2_566
C16 H16A O2 0.95 2.33 3.192(3) 150.9 1_465
C20 H20B O2 0.98 2.33 2.958(3) 121.0 .
C21 H21C O2 0.98 2.53 3.120(3) 118.3 .
C22 H22A O31 0.98 2.44 3.358(3) 156.2 .
C22 H22C I1 0.98 3.15 4.088(3) 161.9 1_655

_refine_diff_density_max         0.532
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.076


####################################################################### 
# 
# 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_asme1
_database_code_depnum_ccdc_archive 'CCDC 1813580'

_audit_update_record             
;
2017-12-27 deposited with the CCDC.
2018-04-09 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H36 N4 O6 S2, 2(CH Cl3)'
_chemical_formula_sum            'C46 H38 Cl6 N4 O6 S2'
_chemical_formula_weight         1019.62

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'
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      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                   8.2494(3)
_cell_length_b                   9.3069(4)
_cell_length_c                   15.1499(7)
_cell_angle_alpha                87.1718(10)
_cell_angle_beta                 78.7559(10)
_cell_angle_gamma                77.6043(9)
_cell_volume                     1114.20(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5146
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      27.69

_exptl_crystal_description       needles
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.381
_exptl_crystal_size_mid          0.027
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    0.535
_shelx_estimated_absorpt_T_min   0.822
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9073
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_process_details   
'based on measured indexed crystal faces, Bruker SHELXTL2014 (Sheldrick, 2014)'


_diffrn_ambient_temperature      100(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            16994
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.370
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5126
_reflns_number_gt                3812
_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-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
All H atoms were positioned geometrically ( C---H = 0.93/1.00 Å) and   
allowed to ride with Uiso(H)= 1.2/1.5Ueq(C).
Methyl ones were allowed to rotate around the corresponding C---C.

 The asymmetric unit consists of a half molecule and a chloroform solvent
 molecule.  There exist a Hydrogen bond between the chloroform proton and the N2
 of the pyridyl group.  
;



_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0590P)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         5126
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.1010
_refine_ls_wR_factor_gt          0.0862
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_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
S1 S 0.18594(6) 0.30756(6) 0.18449(3) 0.01476(12) Uani 1 1 d . . . . .
O1 O 0.92014(18) 0.69520(17) 0.13286(10) 0.0244(4) Uani 1 1 d . . . . .
O2 O 0.5924(2) 0.83245(17) 0.19739(11) 0.0288(4) Uani 1 1 d . . . . .
O3 O 0.44194(17) 0.65495(15) 0.23659(10) 0.0174(3) Uani 1 1 d . . . . .
N1 N 0.68144(19) 0.60373(18) 0.13425(11) 0.0134(3) Uani 1 1 d . . . . .
N2 N -0.4437(2) 0.2408(2) 0.32658(12) 0.0210(4) Uani 1 1 d . . . . .
C1 C 0.8506(2) 0.6147(2) 0.10123(13) 0.0145(4) Uani 1 1 d . . . . .
C2 C 0.9210(2) 0.5037(2) 0.02633(13) 0.0122(4) Uani 1 1 d . . . . .
C3 C 0.7872(2) 0.4201(2) 0.02836(13) 0.0114(4) Uani 1 1 d . . . . .
C4 C 0.7724(2) 0.2979(2) -0.01797(13) 0.0130(4) Uani 1 1 d . . . . .
H4A H 0.8634 0.2530 -0.0633 0.016 Uiso 1 1 calc R U . . .
C5 C 0.6266(2) 0.2421(2) 0.00172(14) 0.0140(4) Uani 1 1 d . . . . .
H5A H 0.6194 0.1593 -0.0304 0.017 Uiso 1 1 calc R U . . .
C6 C 0.4897(2) 0.3053(2) 0.06808(13) 0.0126(4) Uani 1 1 d . . . . .
C7 C 0.5016(2) 0.4273(2) 0.11497(13) 0.0126(4) Uani 1 1 d . . . . .
H7A H 0.4104 0.4720 0.1602 0.015 Uiso 1 1 calc R U . . .
C8 C 0.6474(2) 0.4816(2) 0.09461(13) 0.0123(4) Uani 1 1 d . . . . .
C9 C 0.3318(2) 0.2460(2) 0.08891(13) 0.0123(4) Uani 1 1 d . . . . .
C10 C 0.2778(2) 0.1543(2) 0.04097(14) 0.0151(4) Uani 1 1 d . . . . .
H10A H 0.3415 0.1098 -0.0136 0.018 Uiso 1 1 calc R U . . .
C11 C 0.1147(2) 0.1314(2) 0.08096(14) 0.0147(4) Uani 1 1 d . . . . .
H11A H 0.0583 0.0689 0.0561 0.018 Uiso 1 1 calc R U . . .
C12 C 0.0466(2) 0.2084(2) 0.15916(14) 0.0136(4) Uani 1 1 d . . . . .
C13 C -0.1196(2) 0.2177(2) 0.21710(13) 0.0137(4) Uani 1 1 d . . . . .
C14 C -0.1882(2) 0.3309(2) 0.27987(14) 0.0182(4) Uani 1 1 d . . . . .
H14A H -0.1259 0.4034 0.2863 0.022 Uiso 1 1 calc R U . . .
C15 C -0.3464(3) 0.3368(2) 0.33218(15) 0.0203(5) Uani 1 1 d . . . . .
H15A H -0.3889 0.4137 0.3748 0.024 Uiso 1 1 calc R U . . .
C16 C -0.3776(2) 0.1328(2) 0.26566(14) 0.0179(4) Uani 1 1 d . . . . .
H16A H -0.4443 0.0637 0.2597 0.021 Uiso 1 1 calc R U . . .
C17 C -0.2197(2) 0.1158(2) 0.21145(14) 0.0173(4) Uani 1 1 d . . . . .
H17A H -0.1794 0.0359 0.1708 0.021 Uiso 1 1 calc R U . . .
C18 C 0.5694(3) 0.7107(2) 0.19259(14) 0.0175(4) Uani 1 1 d . . . . .
C19 C 0.2976(3) 0.7463(2) 0.29938(14) 0.0183(4) Uani 1 1 d . . . . .
C20 C 0.2195(3) 0.8833(2) 0.25180(16) 0.0246(5) Uani 1 1 d . . . . .
H20A H 0.1256 0.9416 0.2938 0.037 Uiso 1 1 calc R U . . .
H20B H 0.3050 0.9421 0.2304 0.037 Uiso 1 1 calc R U . . .
H20C H 0.1774 0.8549 0.2005 0.037 Uiso 1 1 calc R U . . .
C21 C 0.3615(3) 0.7803(3) 0.38169(15) 0.0268(5) Uani 1 1 d . . . . .
H21A H 0.2686 0.8400 0.4235 0.040 Uiso 1 1 calc R U . . .
H21B H 0.4050 0.6881 0.4114 0.040 Uiso 1 1 calc R U . . .
H21C H 0.4522 0.8347 0.3633 0.040 Uiso 1 1 calc R U . . .
C22 C 0.1757(3) 0.6421(3) 0.32111(16) 0.0260(5) Uani 1 1 d . . . . .
H22A H 0.0738 0.6901 0.3626 0.039 Uiso 1 1 calc R U . . .
H22B H 0.1446 0.6169 0.2655 0.039 Uiso 1 1 calc R U . . .
H22C H 0.2301 0.5523 0.3493 0.039 Uiso 1 1 calc R U . . .
Cl1 Cl -0.73974(8) 0.08097(7) 0.56622(4) 0.03275(16) Uani 1 1 d . . . . .
Cl2 Cl -0.77138(7) 0.39258(7) 0.52657(4) 0.03181(16) Uani 1 1 d . . . . .
Cl3 Cl -0.93218(7) 0.21552(7) 0.43222(4) 0.03379(16) Uani 1 1 d . . . . .
C23 C -0.7549(3) 0.2171(3) 0.48159(16) 0.0243(5) Uani 1 1 d . . . . .
H23A H -0.6505 0.1949 0.4340 0.029 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
S1 C9 1.726(2) . ?
S1 C12 1.7267(19) . ?
O1 C1 1.203(2) . ?
O2 C18 1.196(2) . ?
O3 C18 1.322(2) . ?
O3 C19 1.500(2) . ?
N1 C1 1.411(2) . ?
N1 C18 1.414(3) . ?
N1 C8 1.415(2) . ?
N2 C15 1.338(3) . ?
N2 C16 1.349(3) . ?
C1 C2 1.514(3) . ?
C2 C2 1.380(4) 2_765 ?
C2 C3 1.475(3) . ?
C3 C4 1.404(3) . ?
C3 C8 1.410(3) . ?
C4 C5 1.385(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.401(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.400(3) . ?
C6 C9 1.493(3) . ?
C7 C8 1.378(3) . ?
C7 H7A 0.9500 . ?
C9 C10 1.344(3) . ?
C10 C11 1.419(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.373(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.465(3) . ?
C13 C17 1.401(3) . ?
C13 C14 1.403(3) . ?
C14 C15 1.380(3) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 C17 1.379(3) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C19 C20 1.516(3) . ?
C19 C21 1.516(3) . ?
C19 C22 1.523(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
Cl1 C23 1.760(2) . ?
Cl2 C23 1.769(2) . ?
Cl3 C23 1.770(2) . ?
C23 H23A 1.0000 . ?

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
C9 S1 C12 91.62(10) . . ?
C18 O3 C19 121.62(16) . . ?
C1 N1 C18 121.45(16) . . ?
C1 N1 C8 109.45(16) . . ?
C18 N1 C8 128.93(16) . . ?
C15 N2 C16 115.84(18) . . ?
O1 C1 N1 123.31(18) . . ?
O1 C1 C2 129.47(18) . . ?
N1 C1 C2 107.13(16) . . ?
C2 C2 C3 133.5(2) 2_765 . ?
C2 C2 C1 121.8(2) 2_765 . ?
C3 C2 C1 104.68(16) . . ?
C4 C3 C8 116.74(16) . . ?
C4 C3 C2 134.92(18) . . ?
C8 C3 C2 108.33(16) . . ?
C5 C4 C3 120.73(18) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 121.32(18) . . ?
C4 C5 H5A 119.3 . . ?
C6 C5 H5A 119.3 . . ?
C7 C6 C5 118.88(17) . . ?
C7 C6 C9 119.70(18) . . ?
C5 C6 C9 121.41(17) . . ?
C8 C7 C6 119.14(18) . . ?
C8 C7 H7A 120.4 . . ?
C6 C7 H7A 120.4 . . ?
C7 C8 C3 123.19(18) . . ?
C7 C8 N1 126.99(18) . . ?
C3 C8 N1 109.82(16) . . ?
C10 C9 C6 129.51(18) . . ?
C10 C9 S1 112.18(14) . . ?
C6 C9 S1 118.20(15) . . ?
C9 C10 C11 112.46(19) . . ?
C9 C10 H10A 123.8 . . ?
C11 C10 H10A 123.8 . . ?
C12 C11 C10 113.31(18) . . ?
C12 C11 H11A 123.3 . . ?
C10 C11 H11A 123.3 . . ?
C11 C12 C13 129.31(18) . . ?
C11 C12 S1 110.42(14) . . ?
C13 C12 S1 120.24(15) . . ?
C17 C13 C14 116.56(18) . . ?
C17 C13 C12 121.75(18) . . ?
C14 C13 C12 121.68(18) . . ?
C15 C14 C13 119.77(19) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
N2 C15 C14 124.1(2) . . ?
N2 C15 H15A 118.0 . . ?
C14 C15 H15A 118.0 . . ?
N2 C16 C17 124.53(19) . . ?
N2 C16 H16A 117.7 . . ?
C17 C16 H16A 117.7 . . ?
C16 C17 C13 119.19(19) . . ?
C16 C17 H17A 120.4 . . ?
C13 C17 H17A 120.4 . . ?
O2 C18 O3 127.9(2) . . ?
O2 C18 N1 122.38(18) . . ?
O3 C18 N1 109.72(17) . . ?
O3 C19 C20 110.59(17) . . ?
O3 C19 C21 108.43(16) . . ?
C20 C19 C21 112.99(19) . . ?
O3 C19 C22 101.52(16) . . ?
C20 C19 C22 110.57(18) . . ?
C21 C19 C22 112.13(19) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Cl1 C23 Cl2 110.44(13) . . ?
Cl1 C23 Cl3 109.99(12) . . ?
Cl2 C23 Cl3 110.22(13) . . ?
Cl1 C23 H23A 108.7 . . ?
Cl2 C23 H23A 108.7 . . ?
Cl3 C23 H23A 108.7 . . ?

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
C23 H23A N2 1.00 2.21 3.162(3) 157.5 .

_refine_diff_density_max         0.581
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.075

_shelxl_version_number           2014/6



