# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_55
_database_code_depnum_ccdc_archive 'CCDC 1518182'
_audit_update_record             
;
2016-11-19 deposited with the CCDC.
2017-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7.75 H7.75 F7.75 N7.75 O7.75 S7.75'
_chemical_formula_weight         729.18

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.086(5)
_cell_length_b                   14.196(5)
_cell_length_c                   23.304(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2675(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.811
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1457
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_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            15683
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_av_sigmaI/netI    0.0917
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4725
_reflns_number_gt                3493
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0753P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.92(14)
_refine_ls_number_reflns         4725
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1534
_refine_ls_wR_factor_gt          0.1363
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.005

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
S1 S 0.27194(14) 0.21888(9) 0.22602(5) 0.0265(3) Uani 1 1 d . . .
S2 S 0.22438(15) 0.27626(9) 0.10522(5) 0.0261(3) Uani 1 1 d . . .
O2 O 0.4126(4) 0.2260(3) 0.26314(13) 0.0354(9) Uani 1 1 d . . .
O3 O 0.2008(4) 0.1290(2) 0.21461(15) 0.0341(9) Uani 1 1 d . . .
O5 O 0.0591(4) 0.2816(3) 0.12675(14) 0.0323(8) Uani 1 1 d . . .
O4 O 0.2935(5) 0.3522(2) 0.07362(15) 0.0356(9) Uani 1 1 d . . .
O1 O 0.4294(5) 0.4402(2) 0.19042(17) 0.0410(10) Uani 1 1 d . . .
N1 N 0.3463(5) 0.2610(3) 0.16295(16) 0.0224(9) Uani 1 1 d . . .
C12 C 0.6381(6) 0.2355(4) 0.1393(2) 0.0283(12) Uani 1 1 d . . .
C25 C 0.1146(6) 0.2934(4) 0.2520(2) 0.0267(12) Uani 1 1 d . . .
C5 C 0.8746(7) 0.5792(4) 0.1397(2) 0.0272(12) Uani 1 1 d . . .
C19 C 0.2430(6) 0.1733(4) 0.0640(2) 0.0296(12) Uani 1 1 d . . .
C10 C 0.5449(7) 0.3941(4) 0.1710(2) 0.0281(12) Uani 1 1 d . . .
C11 C 0.5183(6) 0.2924(4) 0.1577(2) 0.0241(11) Uani 1 1 d . . .
C13 C 0.6338(6) 0.1338(4) 0.1224(2) 0.0307(12) Uani 1 1 d . . .
C3 C 1.1684(7) 0.5809(4) 0.1208(2) 0.0401(15) Uani 1 1 d . . .
H3 H 1.2711 0.5518 0.1237 0.048 Uiso 1 1 calc R . .
C8 C 0.7196(7) 0.5305(3) 0.1568(2) 0.0306(12) Uani 1 1 d . . .
C2 C 1.1549(7) 0.6672(4) 0.0950(2) 0.0352(14) Uani 1 1 d . . .
C6 C 0.8656(7) 0.6698(3) 0.1167(2) 0.0314(13) Uani 1 1 d . . .
H6 H 0.7649 0.7015 0.1171 0.038 Uiso 1 1 calc R . .
C26 C -0.0467(6) 0.2590(4) 0.2543(2) 0.0342(14) Uani 1 1 d . . .
H26 H -0.0717 0.1999 0.2395 0.041 Uiso 1 1 calc R . .
C7 C 1.0030(7) 0.7136(4) 0.0934(2) 0.0395(14) Uani 1 1 d . . .
H7 H 0.9941 0.7731 0.0769 0.047 Uiso 1 1 calc R . .
C4 C 1.0297(7) 0.5372(4) 0.1424(2) 0.0343(14) Uani 1 1 d . . .
H4 H 1.0401 0.4781 0.1592 0.041 Uiso 1 1 calc R . .
F3 F 1.3937(7) 0.6575(3) 0.0388(3) 0.125(2) Uani 1 1 d . . .
C30 C 0.1537(7) 0.3805(4) 0.2733(3) 0.0406(14) Uani 1 1 d . . .
H30 H 0.2619 0.4026 0.2719 0.049 Uiso 1 1 calc R . .
C1 C 1.3051(9) 0.7119(5) 0.0704(3) 0.0562(18) Uani 1 1 d . . .
C9 C 0.7073(6) 0.4362(3) 0.1590(2) 0.0298(12) Uani 1 1 d . . .
F1 F 1.4148(6) 0.7388(5) 0.1090(2) 0.132(2) Uani 1 1 d . . .
C22 C 0.2674(9) 0.0116(4) 0.0000(3) 0.0524(17) Uani 1 1 d . . .
H22 H 0.2750 -0.0431 -0.0218 0.063 Uiso 1 1 calc R . .
C24 C 0.3507(8) 0.1700(4) 0.0185(2) 0.0400(14) Uani 1 1 d . . .
H24 H 0.4147 0.2224 0.0095 0.048 Uiso 1 1 calc R . .
C18 C 0.7221(8) 0.1090(4) 0.0741(3) 0.0470(15) Uani 1 1 d . . .
H18 H 0.7812 0.1550 0.0544 0.056 Uiso 1 1 calc R . .
C14 C 0.5509(7) 0.0637(4) 0.1524(3) 0.0458(16) Uani 1 1 d . . .
H14 H 0.4926 0.0779 0.1857 0.055 Uiso 1 1 calc R . .
C23 C 0.3642(9) 0.0887(5) -0.0139(3) 0.0509(17) Uani 1 1 d . . .
H23 H 0.4373 0.0859 -0.0447 0.061 Uiso 1 1 calc R . .
C27 C -0.1691(7) 0.3138(4) 0.2788(2) 0.0438(16) Uani 1 1 d . . .
H27 H -0.2769 0.2914 0.2814 0.053 Uiso 1 1 calc R . .
C16 C 0.6390(8) -0.0504(4) 0.0829(3) 0.0564(19) Uani 1 1 d . . .
H16 H 0.6368 -0.1118 0.0690 0.068 Uiso 1 1 calc R . .
C20 C 0.1455(8) 0.0957(4) 0.0776(3) 0.0433(15) Uani 1 1 d . . .
H20 H 0.0709 0.0982 0.1079 0.052 Uiso 1 1 calc R . .
C28 C -0.1292(8) 0.4026(5) 0.2994(3) 0.0466(16) Uani 1 1 d . . .
H28 H -0.2113 0.4405 0.3152 0.056 Uiso 1 1 calc R . .
C21 C 0.1613(9) 0.0151(4) 0.0452(3) 0.0490(17) Uani 1 1 d . . .
H21 H 0.0986 -0.0377 0.0545 0.059 Uiso 1 1 calc R . .
C29 C 0.0298(8) 0.4348(4) 0.2967(3) 0.0492(17) Uani 1 1 d . . .
H29 H 0.0548 0.4943 0.3110 0.059 Uiso 1 1 calc R . .
C15 C 0.5565(8) -0.0286(4) 0.1317(3) 0.0547(19) Uani 1 1 d . . .
H15 H 0.5025 -0.0761 0.1518 0.066 Uiso 1 1 calc R . .
C17 C 0.7247(9) 0.0166(4) 0.0542(3) 0.0505(16) Uani 1 1 d . . .
H17 H 0.7848 0.0010 0.0215 0.061 Uiso 1 1 calc R . .
F2 F 1.2781(6) 0.7860(4) 0.0413(4) 0.183(4) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O3 1.425(3) . ?
S1 O2 1.433(3) . ?
S1 N1 1.697(4) . ?
S1 C25 1.762(5) . ?
S2 O4 1.420(4) . ?
S2 O5 1.429(3) . ?
S2 N1 1.682(4) . ?
S2 C19 1.756(5) . ?
O1 C10 1.227(6) . ?
N1 C11 1.465(6) . ?
C12 C11 1.333(7) . ?
C12 C13 1.496(7) . ?
C25 C30 1.370(7) . ?
C25 C26 1.393(7) . ?
C5 C6 1.395(7) . ?
C5 C4 1.390(7) . ?
C5 C8 1.485(7) . ?
C19 C24 1.372(7) . ?
C19 C20 1.392(7) . ?
C10 C9 1.470(7) . ?
C10 C11 1.492(7) . ?
C13 C18 1.378(8) . ?
C13 C14 1.389(7) . ?
C3 C2 1.370(8) . ?
C3 C4 1.377(7) . ?
C8 C9 1.343(7) . ?
C2 C7 1.394(8) . ?
C2 C1 1.485(8) . ?
C6 C7 1.385(7) . ?
C26 C27 1.382(7) . ?
F3 C1 1.286(8) . ?
C30 C29 1.377(8) . ?
C1 F2 1.270(8) . ?
C1 F1 1.319(8) . ?
C22 C21 1.361(9) . ?
C22 C23 1.383(9) . ?
C24 C23 1.385(8) . ?
C18 C17 1.392(8) . ?
C14 C15 1.397(8) . ?
C27 C28 1.387(8) . ?
C16 C17 1.353(9) . ?
C16 C15 1.354(9) . ?
C20 C21 1.375(8) . ?
C28 C29 1.366(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O2 119.8(2) . . ?
O3 S1 N1 107.3(2) . . ?
O2 S1 N1 102.5(2) . . ?
O3 S1 C25 108.1(2) . . ?
O2 S1 C25 108.9(2) . . ?
N1 S1 C25 110.0(2) . . ?
O4 S2 O5 120.7(2) . . ?
O4 S2 N1 106.4(2) . . ?
O5 S2 N1 105.9(2) . . ?
O4 S2 C19 108.3(2) . . ?
O5 S2 C19 108.5(2) . . ?
N1 S2 C19 106.3(2) . . ?
C11 N1 S2 116.8(3) . . ?
C11 N1 S1 121.0(3) . . ?
S2 N1 S1 122.0(2) . . ?
C11 C12 C13 130.7(5) . . ?
C30 C25 C26 121.2(5) . . ?
C30 C25 S1 120.0(4) . . ?
C26 C25 S1 118.6(4) . . ?
C6 C5 C4 117.4(5) . . ?
C6 C5 C8 119.2(5) . . ?
C4 C5 C8 123.3(5) . . ?
C24 C19 C20 120.6(5) . . ?
C24 C19 S2 120.3(4) . . ?
C20 C19 S2 119.1(4) . . ?
O1 C10 C9 122.2(5) . . ?
O1 C10 C11 118.8(5) . . ?
C9 C10 C11 118.9(5) . . ?
C12 C11 N1 122.2(5) . . ?
C12 C11 C10 123.3(5) . . ?
N1 C11 C10 114.4(4) . . ?
C18 C13 C14 118.5(5) . . ?
C18 C13 C12 116.7(5) . . ?
C14 C13 C12 124.8(5) . . ?
C2 C3 C4 119.9(5) . . ?
C9 C8 C5 122.4(5) . . ?
C3 C2 C7 120.3(5) . . ?
C3 C2 C1 119.1(6) . . ?
C7 C2 C1 120.6(5) . . ?
C5 C6 C7 121.5(5) . . ?
C27 C26 C25 119.3(5) . . ?
C6 C7 C2 119.0(5) . . ?
C3 C4 C5 121.7(5) . . ?
C25 C30 C29 118.7(6) . . ?
F2 C1 F3 106.7(6) . . ?
F2 C1 F1 103.9(7) . . ?
F3 C1 F1 100.9(7) . . ?
F2 C1 C2 114.8(6) . . ?
F3 C1 C2 114.9(5) . . ?
F1 C1 C2 114.3(5) . . ?
C8 C9 C10 118.6(5) . . ?
C21 C22 C23 120.6(6) . . ?
C19 C24 C23 119.9(6) . . ?
C13 C18 C17 121.4(6) . . ?
C13 C14 C15 118.9(6) . . ?
C22 C23 C24 119.2(6) . . ?
C26 C27 C28 119.2(5) . . ?
C17 C16 C15 120.5(6) . . ?
C21 C20 C19 118.7(6) . . ?
C29 C28 C27 120.5(5) . . ?
C22 C21 C20 120.9(6) . . ?
C28 C29 C30 121.0(6) . . ?
C16 C15 C14 121.3(6) . . ?
C16 C17 C18 119.3(6) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.068
