# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_d19031
_database_code_depnum_ccdc_archive 'CCDC 1815763'
_audit_update_record             
;
2018-02-10 deposited with the CCDC.
2018-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 F2 N2 S1'
_chemical_formula_sum            'C60 H42 Cl4 F2 N2 S'
_chemical_formula_weight         1002.82

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1294(12)
_cell_length_b                   9.2735(13)
_cell_length_c                   16.422(2)
_cell_angle_alpha                93.116(4)
_cell_angle_beta                 97.317(4)
_cell_angle_gamma                115.044(4)
_cell_volume                     1240.2(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             518
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.8039
_exptl_absorpt_correction_T_max  0.9645
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32746
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         25.04
_reflns_number_total             4314
_reflns_number_gt                3948
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0440P)²+0.9596P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4314
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1147
_refine_ls_wR_factor_gt          0.1107
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0310(2) 0.3754(2) 0.47248(11) 0.0243(4) Uani 1 1 d . . .
C2 C 0.1356(2) 0.4718(2) 0.54367(10) 0.0239(4) Uani 1 1 d . . .
C3 C -0.1006(2) 0.4019(2) 0.43059(10) 0.0244(4) Uani 1 1 d . . .
C4 C 0.2718(2) 0.4423(2) 0.58649(10) 0.0250(4) Uani 1 1 d . . .
C5 C 0.2473(2) 0.2884(2) 0.60289(11) 0.0262(4) Uani 1 1 d . B .
H5 H 0.1420 0.2011 0.5870 0.031 Uiso 1 1 calc R . .
C6 C 0.3756(2) 0.2620(2) 0.64219(11) 0.0259(4) Uani 1 1 d . . .
H6 H 0.3568 0.1563 0.6525 0.031 Uiso 1 1 calc R B .
C7 C 0.5321(2) 0.3872(2) 0.66698(10) 0.0236(4) Uani 1 1 d . B .
C8 C 0.5559(2) 0.5398(2) 0.64916(12) 0.0298(4) Uani 1 1 d . . .
H8 H 0.6618 0.6266 0.6640 0.036 Uiso 1 1 calc R B .
C9 C 0.4279(2) 0.5674(2) 0.61019(12) 0.0304(4) Uani 1 1 d . B .
H9 H 0.4470 0.6730 0.5995 0.037 Uiso 1 1 calc R . .
C10 C 0.6686(2) 0.3543(2) 0.70811(10) 0.0239(4) Uani 1 1 d . . .
C11 C 0.6846(2) 0.2154(2) 0.66728(11) 0.0242(4) Uani 1 1 d . B .
C12 C 0.6799(2) 0.1992(2) 0.58210(11) 0.0307(4) Uani 1 1 d . . .
H12 H 0.6603 0.2736 0.5502 0.037 Uiso 1 1 calc R B .
C13 C 0.7036(3) 0.0762(2) 0.54312(13) 0.0394(5) Uani 1 1 d . B .
H13 H 0.7012 0.0674 0.4850 0.047 Uiso 1 1 calc R . .
C14 C 0.7306(3) -0.0336(2) 0.58873(15) 0.0437(5) Uani 1 1 d . . .
H14 H 0.7491 -0.1168 0.5624 0.052 Uiso 1 1 calc R B .
C15 C 0.7305(3) -0.0213(2) 0.67278(15) 0.0452(5) Uani 1 1 d . B .
H15 H 0.7470 -0.0978 0.7042 0.054 Uiso 1 1 calc R . .
C16 C 0.7067(2) 0.1007(2) 0.71183(12) 0.0342(4) Uani 1 1 d . . .
H16 H 0.7053 0.1065 0.7696 0.041 Uiso 1 1 calc R B .
C17 C 0.7730(2) 0.4451(2) 0.77683(10) 0.0236(4) Uani 1 1 d . B .
C18 C 0.9157(2) 0.4175(2) 0.81418(10) 0.0236(4) Uani 1 1 d . . .
C19 C 1.0364(2) 0.4209(2) 0.76969(11) 0.0308(4) Uani 1 1 d . B .
H19 H 1.0311 0.4448 0.7142 0.037 Uiso 1 1 calc R . .
C20 C 1.1642(2) 0.3901(3) 0.80510(12) 0.0388(5) Uani 1 1 d . . .
H20 H 1.2472 0.3948 0.7743 0.047 Uiso 1 1 calc R B .
C21 C 1.1714(2) 0.3523(3) 0.88547(12) 0.0378(5) Uani 1 1 d . B .
H21 H 1.2575 0.3279 0.9093 0.045 Uiso 1 1 calc R . .
C22 C 1.0538(2) 0.3500(2) 0.93074(11) 0.0349(4) Uani 1 1 d . . .
H22 H 1.0588 0.3244 0.9860 0.042 Uiso 1 1 calc R B .
C23 C 0.9281(2) 0.3850(2) 0.89582(11) 0.0294(4) Uani 1 1 d . B .
H23 H 0.8493 0.3867 0.9280 0.035 Uiso 1 1 calc R . .
C24 C 0.7538(2) 0.5764(2) 0.82433(11) 0.0271(4) Uani 1 1 d . . .
C25 C 0.8773(3) 0.7314(2) 0.83516(12) 0.0361(4) Uani 1 1 d . B .
H25 H 0.9714 0.7548 0.8098 0.043 Uiso 1 1 calc R . .
C26 C 0.8649(3) 0.8534(3) 0.88278(14) 0.0480(6) Uani 1 1 d . . .
H26 H 0.9495 0.9597 0.8891 0.058 Uiso 1 1 calc R B .
C27 C 0.7300(3) 0.8198(3) 0.92078(14) 0.0529(7) Uani 1 1 d . B .
H27 H 0.7215 0.9027 0.9536 0.064 Uiso 1 1 calc R . .
C28 C 0.6074(3) 0.6659(3) 0.91105(14) 0.0492(6) Uani 1 1 d . . .
H28 H 0.5148 0.6426 0.9377 0.059 Uiso 1 1 calc R B .
C29 C 0.6180(2) 0.5445(3) 0.86272(13) 0.0372(5) Uani 1 1 d . B .
H29 H 0.5319 0.4389 0.8558 0.045 Uiso 1 1 calc R . .
C30 C 0.6326(4) 0.1193(4) 0.14538(19) 0.0757(9) Uani 1 1 d . . .
H30A H 0.5140 0.0909 0.1398 0.091 Uiso 1 1 calc R . .
H30B H 0.6910 0.2079 0.1909 0.091 Uiso 1 1 calc R . .
F1 F -0.1767(19) 0.297(2) 0.3672(10) 0.0265(19) Uani 0.50 1 d P A 2
F1' F 0.0487(12) 0.2529(12) 0.4379(6) 0.038(3) Uani 0.50 1 d P B 3
N1 N 0.0483(17) 0.2506(15) 0.4353(8) 0.028(4) Uani 0.50 1 d P B 1
N1' N -0.202(3) 0.298(3) 0.3558(15) 0.026(2) Uani 0.50 1 d P B 1
S1 S -0.09386(12) 0.17654(11) 0.35575(6) 0.0313(2) Uani 0.50 1 d P B 1
Cl1 Cl 0.70003(9) 0.18373(8) 0.05429(4) 0.0619(2) Uani 1 1 d . . .
Cl2 Cl 0.66510(12) -0.04645(10) 0.17032(6) 0.0881(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 F1' 1.322(9) . ?
C1 N1 1.357(10) . ?
C1 C2 1.399(3) . ?
C1 C3 1.426(2) . ?
C2 C3 1.397(2) 2_566 ?
C2 C4 1.483(2) . ?
C3 F1 1.285(16) . ?
C3 C2 1.397(2) 2_566 ?
C3 N1' 1.46(2) . ?
C4 C9 1.392(3) . ?
C4 C5 1.396(2) . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.396(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(2) . ?
C7 C10 1.494(2) . ?
C8 C9 1.386(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C17 1.354(2) . ?
C10 C11 1.490(2) . ?
C11 C16 1.391(3) . ?
C11 C12 1.392(3) . ?
C12 C13 1.387(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.494(2) . ?
C17 C24 1.495(2) . ?
C18 C19 1.389(2) . ?
C18 C23 1.391(2) . ?
C19 C20 1.382(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.375(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.385(3) . ?
C24 C29 1.390(3) . ?
C25 C26 1.392(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.377(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.376(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.386(3) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 Cl1 1.730(3) . ?
C30 Cl2 1.744(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
N1 S1 1.606(14) . ?
N1' S1 1.79(2) . ?

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
F1' C1 N1 1.3(10) . . ?
F1' C1 C2 122.1(4) . . ?
N1 C1 C2 123.1(6) . . ?
F1' C1 C3 114.6(4) . . ?
N1 C1 C3 113.6(6) . . ?
C2 C1 C3 123.35(17) . . ?
C3 C2 C1 113.66(16) 2_566 . ?
C3 C2 C4 123.73(15) 2_566 . ?
C1 C2 C4 122.60(16) . . ?
F1 C3 C2 126.4(6) . 2_566 ?
F1 C3 C1 110.6(6) . . ?
C2 C3 C1 122.99(16) 2_566 . ?
F1 C3 N1' 9.4(15) . . ?
C2 C3 N1' 117.0(9) 2_566 . ?
C1 C3 N1' 120.0(9) . . ?
C9 C4 C5 118.33(16) . . ?
C9 C4 C2 120.76(16) . . ?
C5 C4 C2 120.91(15) . . ?
C6 C5 C4 120.42(16) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 121.55(16) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 117.59(15) . . ?
C8 C7 C10 122.14(15) . . ?
C6 C7 C10 120.23(15) . . ?
C9 C8 C7 121.22(17) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C4 120.86(17) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
C17 C10 C11 121.80(15) . . ?
C17 C10 C7 122.92(15) . . ?
C11 C10 C7 115.27(14) . . ?
C16 C11 C12 118.18(17) . . ?
C16 C11 C10 122.07(16) . . ?
C12 C11 C10 119.75(15) . . ?
C13 C12 C11 120.96(18) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 120.03(19) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 119.39(18) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.79(19) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C11 120.59(19) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C10 C17 C18 122.38(15) . . ?
C10 C17 C24 123.91(15) . . ?
C18 C17 C24 113.66(14) . . ?
C19 C18 C23 118.33(16) . . ?
C19 C18 C17 122.19(15) . . ?
C23 C18 C17 119.47(15) . . ?
C20 C19 C18 120.88(17) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 119.98(18) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 119.91(17) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.01(17) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C18 120.82(17) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?
C25 C24 C29 118.69(18) . . ?
C25 C24 C17 120.06(17) . . ?
C29 C24 C17 121.13(17) . . ?
C24 C25 C26 120.7(2) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C27 C26 C25 119.9(2) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C28 C27 C26 119.8(2) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C27 C28 C29 120.5(2) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C28 C29 C24 120.3(2) . . ?
C28 C29 H29 119.8 . . ?
C24 C29 H29 119.8 . . ?
Cl1 C30 Cl2 112.14(17) . . ?
Cl1 C30 H30A 109.2 . . ?
Cl2 C30 H30A 109.2 . . ?
Cl1 C30 H30B 109.2 . . ?
Cl2 C30 H30B 109.2 . . ?
H30A C30 H30B 107.9 . . ?
C1 N1 S1 106.5(8) . . ?
C3 N1' S1 94.6(10) . . ?
N1 S1 N1' 105.3(8) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.041
