# 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_20160510a2_0m
_database_code_depnum_ccdc_archive 'CCDC 1500701'
_audit_update_record             
;
2016-08-23 deposited with the CCDC.
2017-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H21 N O2 S2'
_chemical_formula_sum            'C27 H21 N O2 S2'
_chemical_formula_weight         455.57

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   5.9608(4)
_cell_length_b                   18.7773(9)
_cell_length_c                   20.3817(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2281.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9958
_cell_measurement_theta_min      3.1886
_cell_measurement_theta_max      26.9840

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9746
_exptl_absorpt_correction_T_max  0.9796
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24626
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4001
_reflns_number_gt                3574
_reflns_threshold_expression     >2sigma(I)

__computing_data_collection      'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0529P)²+0.2657P] 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   -0.02(7)
_refine_ls_number_reflns         4001
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3602(3) 0.88030(10) 0.70328(9) 0.0348(4) Uani 1 1 d . . .
C2 C 0.5042(4) 0.86304(11) 0.65403(9) 0.0398(5) Uani 1 1 d . . .
C3 C 0.4378(4) 0.79516(10) 0.62671(9) 0.0405(4) Uani 1 1 d . . .
C4 C 0.5247(5) 0.75508(13) 0.57487(10) 0.0551(6) Uani 1 1 d . . .
H4 H 0.6538 0.7692 0.5528 0.066 Uiso 1 1 calc R . .
C5 C 0.4118(6) 0.69389(13) 0.55766(12) 0.0643(7) Uani 1 1 d . . .
H5 H 0.4672 0.6657 0.5238 0.077 Uiso 1 1 calc R . .
C6 C 0.2186(6) 0.67357(12) 0.58962(12) 0.0628(8) Uani 1 1 d . . .
H6 H 0.1452 0.6324 0.5761 0.075 Uiso 1 1 calc R . .
C7 C 0.1302(5) 0.71229(10) 0.64105(11) 0.0537(6) Uani 1 1 d . . .
H7 H -0.0003 0.6982 0.6624 0.064 Uiso 1 1 calc R . .
C8 C 0.2467(4) 0.77374(10) 0.65940(9) 0.0402(5) Uani 1 1 d . . .
C9 C 0.3562(3) 0.94677(10) 0.74126(10) 0.0362(5) Uani 1 1 d . . .
C10 C 0.1763(4) 0.99420(11) 0.73642(12) 0.0522(6) Uani 1 1 d . . .
H10 H 0.0499 0.9819 0.7122 0.063 Uiso 1 1 calc R . .
C11 C 0.1863(5) 1.05930(12) 0.76761(14) 0.0637(7) Uani 1 1 d . . .
H11 H 0.0658 1.0905 0.7645 0.076 Uiso 1 1 calc R . .
C12 C 0.3721(5) 1.07859(12) 0.80325(13) 0.0574(6) Uani 1 1 d . . .
H12 H 0.3788 1.1231 0.8231 0.069 Uiso 1 1 calc R . .
C13 C 0.5468(4) 1.03214(12) 0.80933(12) 0.0518(6) Uani 1 1 d . . .
H13 H 0.6709 1.0446 0.8345 0.062 Uiso 1 1 calc R . .
C14 C 0.5409(4) 0.96650(11) 0.77831(10) 0.0436(5) Uani 1 1 d . . .
H14 H 0.6617 0.9355 0.7824 0.052 Uiso 1 1 calc R . .
C15 C 0.2738(4) 0.75925(11) 0.82401(10) 0.0445(5) Uani 1 1 d . . .
C16 C 0.3036(6) 0.68632(13) 0.81748(13) 0.0683(8) Uani 1 1 d . . .
H16 H 0.2141 0.6606 0.7886 0.082 Uiso 1 1 calc R . .
C17 C 0.4649(6) 0.65217(15) 0.85361(15) 0.0775(9) Uani 1 1 d . . .
H17 H 0.4826 0.6032 0.8491 0.093 Uiso 1 1 calc R . .
C18 C 0.5995(6) 0.68829(17) 0.89587(14) 0.0727(8) Uani 1 1 d . . .
C19 C 0.5717(6) 0.76181(17) 0.90165(14) 0.0802(9) Uani 1 1 d . . .
H19 H 0.6638 0.7875 0.9299 0.096 Uiso 1 1 calc R . .
C20 C 0.4091(5) 0.79687(13) 0.86591(13) 0.0638(7) Uani 1 1 d . . .
H20 H 0.3914 0.8459 0.8702 0.077 Uiso 1 1 calc R . .
C21 C 0.7846(7) 0.6510(2) 0.9343(2) 0.1196(15) Uani 1 1 d . . .
H21A H 0.7215 0.6125 0.9592 0.179 Uiso 1 1 calc R . .
H21B H 0.8544 0.6844 0.9636 0.179 Uiso 1 1 calc R . .
H21C H 0.8947 0.6327 0.9044 0.179 Uiso 1 1 calc R . .
C22 C 0.6043(4) 0.95635(11) 0.55404(11) 0.0459(5) Uani 1 1 d . . .
C23 C 0.7388(6) 1.00418(15) 0.52051(14) 0.0717(8) Uani 1 1 d . . .
H23 H 0.8803 1.0155 0.5366 0.086 Uiso 1 1 calc R . .
C24 C 0.6624(8) 1.03547(15) 0.46249(16) 0.0872(11) Uani 1 1 d . . .
H24 H 0.7526 1.0681 0.4405 0.105 Uiso 1 1 calc R . .
C25 C 0.4581(7) 1.01862(16) 0.43797(16) 0.0814(10) Uani 1 1 d . . .
H25 H 0.4103 1.0384 0.3985 0.098 Uiso 1 1 calc R . .
C26 C 0.3224(5) 0.97261(14) 0.47123(12) 0.0651(7) Uani 1 1 d . . .
H26 H 0.1807 0.9620 0.4549 0.078 Uiso 1 1 calc R . .
C27 C 0.3945(4) 0.94144(12) 0.52942(11) 0.0504(6) Uani 1 1 d . . .
H27 H 0.3003 0.9103 0.5518 0.060 Uiso 1 1 calc R . .
N1 N 0.1943(3) 0.82616(8) 0.70777(7) 0.0373(4) Uani 1 1 d . . .
O1 O -0.1019(3) 0.75316(10) 0.75997(9) 0.0678(5) Uani 1 1 d . . .
O2 O 0.0107(3) 0.86726(9) 0.81092(8) 0.0577(4) Uani 1 1 d . . .
S1 S 0.06704(9) 0.80275(3) 0.77845(3) 0.04412(15) Uani 1 1 d . . .
S2 S 0.72212(10) 0.91657(4) 0.62515(3) 0.05779(19) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.360(3) . ?
C1 N1 1.421(2) . ?
C1 C9 1.469(3) . ?
C2 C3 1.446(3) . ?
C2 S2 1.745(2) . ?
C3 C8 1.380(3) . ?
C3 C4 1.397(3) . ?
C4 C5 1.377(4) . ?
C5 C6 1.377(4) . ?
C6 C7 1.380(4) . ?
C7 C8 1.397(3) . ?
C8 N1 1.428(3) . ?
C9 C14 1.385(3) . ?
C9 C10 1.398(3) . ?
C10 C11 1.379(3) . ?
C11 C12 1.373(4) . ?
C12 C13 1.364(4) . ?
C13 C14 1.386(3) . ?
C15 C20 1.371(3) . ?
C15 C16 1.387(3) . ?
C15 S1 1.746(2) . ?
C16 C17 1.370(4) . ?
C17 C18 1.359(4) . ?
C18 C19 1.396(4) . ?
C18 C21 1.523(4) . ?
C19 C20 1.380(4) . ?
C22 C27 1.376(4) . ?
C22 C23 1.384(3) . ?
C22 S2 1.775(2) . ?
C23 C24 1.397(5) . ?
C24 C25 1.354(5) . ?
C25 C26 1.364(4) . ?
C26 C27 1.391(3) . ?
N1 S1 1.6865(17) . ?
O1 S1 1.4223(18) . ?
O2 S1 1.4207(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 108.44(17) . . ?
C2 C1 C9 126.99(18) . . ?
N1 C1 C9 124.24(18) . . ?
C1 C2 C3 108.76(19) . . ?
C1 C2 S2 125.57(16) . . ?
C3 C2 S2 125.56(16) . . ?
C8 C3 C4 120.9(2) . . ?
C8 C3 C2 107.27(18) . . ?
C4 C3 C2 131.7(2) . . ?
C5 C4 C3 117.5(3) . . ?
C6 C5 C4 121.3(2) . . ?
C5 C6 C7 122.2(2) . . ?
C6 C7 C8 116.7(3) . . ?
C3 C8 C7 121.4(2) . . ?
C3 C8 N1 108.24(17) . . ?
C7 C8 N1 130.2(2) . . ?
C14 C9 C10 118.54(18) . . ?
C14 C9 C1 120.11(18) . . ?
C10 C9 C1 121.11(18) . . ?
C11 C10 C9 119.9(2) . . ?
C12 C11 C10 120.8(2) . . ?
C13 C12 C11 119.7(2) . . ?
C12 C13 C14 120.5(2) . . ?
C9 C14 C13 120.4(2) . . ?
C20 C15 C16 119.5(2) . . ?
C20 C15 S1 120.38(17) . . ?
C16 C15 S1 120.1(2) . . ?
C17 C16 C15 120.0(3) . . ?
C18 C17 C16 121.4(3) . . ?
C17 C18 C19 118.5(3) . . ?
C17 C18 C21 121.6(3) . . ?
C19 C18 C21 119.8(3) . . ?
C20 C19 C18 120.7(3) . . ?
C15 C20 C19 119.8(2) . . ?
C27 C22 C23 118.6(3) . . ?
C27 C22 S2 124.85(18) . . ?
C23 C22 S2 116.5(2) . . ?
C22 C23 C24 120.1(3) . . ?
C25 C24 C23 120.5(3) . . ?
C24 C25 C26 119.9(3) . . ?
C25 C26 C27 120.5(3) . . ?
C22 C27 C26 120.4(2) . . ?
C1 N1 C8 107.25(17) . . ?
C1 N1 S1 123.68(13) . . ?
C8 N1 S1 120.57(13) . . ?
O2 S1 O1 120.93(12) . . ?
O2 S1 N1 106.39(9) . . ?
O1 S1 N1 105.25(10) . . ?
O2 S1 C15 108.55(10) . . ?
O1 S1 C15 109.53(11) . . ?
N1 S1 C15 104.99(10) . . ?
C2 S2 C22 102.90(10) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.039
