# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_AG_HC_364
_audit_block_doi                 10.5517/ccdc.csd.cc1mwyp4
_database_code_depnum_ccdc_archive 'CCDC 1516417'
_audit_update_record             
;
2016-11-10 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT026_AG_HC_364           
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..         36 %
RESPONSE: The crystal diffracted weakly so low sigma values were selected.
;
# Added during the CSD deposition process: Thursday 10 November 2016 06:37 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014
_chemical_name_systematic        'Indole-C3-thio pyridine derivative1'
_chemical_name_common            'Indole-C3-thio pyridine derivative1'
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 N2 S'
_chemical_formula_sum            'C23 H20 N2 S'
_chemical_formula_weight         356.47

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'
S S 0.1246 0.1234 '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                   14.207(5)
_cell_length_b                   5.497(5)
_cell_length_c                   24.708(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 106.065(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1854.2(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4793
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      28.8

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      1.28
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.183
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6356
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean 10.233
_diffrn_reflns_number            35666
_diffrn_reflns_av_unetI/netI     0.1609
_diffrn_reflns_av_R_equivalents  0.1728
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.593
_diffrn_reflns_theta_max         28.801
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4793
_reflns_number_gt                1736
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'APEX2 (Bruker, 2014); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014);XPREP(Sheldrick,2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep, Pluton'
_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)+(0.0471P)²+0.5508P] 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         4793
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2434
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.1534
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_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 0.54268(6) 0.09488(15) 0.56862(3) 0.0674(3) Uani 1 1 d . . . . .
N1 N 0.7323(2) 0.4067(4) 0.50121(9) 0.0611(7) Uani 1 1 d . . . . .
N2 N 0.46266(18) 0.2410(5) 0.64491(11) 0.0658(7) Uani 1 1 d . . . . .
C14 C 0.8582(3) 0.4272(11) 0.3386(2) 0.1189(17) Uani 1 1 d . . . . .
H14 H 0.9042 0.4886 0.3218 0.143 Uiso 1 1 calc R U . . .
C10 C 0.7758(2) 0.4484(6) 0.41135(12) 0.0575(8) Uani 1 1 d . . . . .
C17 C 0.6117(2) 0.4544(5) 0.64954(11) 0.0532(8) Uani 1 1 d . . . . .
H17 H 0.6653 0.4763 0.6354 0.064 Uiso 1 1 calc R U . . .
C4 C 0.7401(2) 0.1002(5) 0.56238(11) 0.0520(7) Uani 1 1 d . . . . .
C16 C 0.5408(2) 0.2834(5) 0.62672(11) 0.0520(7) Uani 1 1 d . . . . .
C11 C 0.7248(2) 0.2450(6) 0.38818(13) 0.0704(9) Uani 1 1 d . . . . .
H11 H 0.6787 0.1798 0.4044 0.084 Uiso 1 1 calc R U . . .
C3 C 0.7938(2) 0.2342(5) 0.53246(11) 0.0537(8) Uani 1 1 d . . . . .
C1 C 0.6433(2) 0.1993(5) 0.54753(11) 0.0561(8) Uani 1 1 d . . . . .
C19 C 0.5203(2) 0.5530(6) 0.71391(12) 0.0605(8) Uani 1 1 d . . . . .
C20 C 0.6005(2) 0.5924(5) 0.69421(11) 0.0526(7) Uani 1 1 d . . . . .
C21 C 0.6620(2) 0.7960(6) 0.72592(12) 0.0703(9) Uani 1 1 d . . . . .
H21A H 0.6563 0.9402 0.7026 0.084 Uiso 1 1 calc R U . . .
H21B H 0.7304 0.7488 0.7388 0.084 Uiso 1 1 calc R U . . .
C15 C 0.8055(4) 0.2284(11) 0.31706(18) 0.1150(15) Uani 1 1 d . . . . .
H15 H 0.8145 0.1552 0.2849 0.138 Uiso 1 1 calc R U . . .
C8 C 0.8911(3) 0.1833(6) 0.53642(13) 0.0669(9) Uani 1 1 d . . . . .
H8 H 0.9255 0.2742 0.5165 0.080 Uiso 1 1 calc R U . . .
C5 C 0.7873(3) -0.0910(6) 0.59664(12) 0.0643(8) Uani 1 1 d . . . . .
H5 H 0.7535 -0.1833 0.6167 0.077 Uiso 1 1 calc R U . . .
C9 C 0.7568(2) 0.5771(6) 0.46150(12) 0.0710(9) Uani 1 1 d . . . . .
H9A H 0.8146 0.6690 0.4809 0.085 Uiso 1 1 calc R U . . .
H9B H 0.7033 0.6913 0.4483 0.085 Uiso 1 1 calc R U . . .
C2 C 0.6421(2) 0.3829(6) 0.51021(12) 0.0633(8) Uani 1 1 d . . . . .
H2 H 0.5878 0.4781 0.4934 0.076 Uiso 1 1 calc R U . . .
C6 C 0.8832(3) -0.1420(6) 0.60053(13) 0.0748(9) Uani 1 1 d . . . . .
H6 H 0.9144 -0.2693 0.6233 0.090 Uiso 1 1 calc R U . . .
C18 C 0.4547(3) 0.3792(7) 0.68847(15) 0.0783(10) Uani 1 1 d . . . . .
H18 H 0.4007 0.3541 0.7021 0.094 Uiso 1 1 calc R U . . .
C7 C 0.9351(2) -0.0045(6) 0.57051(14) 0.0737(9) Uani 1 1 d . . . . .
H7 H 1.0004 -0.0413 0.5738 0.088 Uiso 1 1 calc R U . . .
C13 C 0.7403(3) 0.1353(7) 0.34148(15) 0.0904(11) Uani 1 1 d . . . . .
H13 H 0.7055 -0.0041 0.3268 0.108 Uiso 1 1 calc R U . . .
C12 C 0.8436(3) 0.5415(7) 0.38654(17) 0.0917(12) Uani 1 1 d . . . . .
H12 H 0.8795 0.6792 0.4014 0.110 Uiso 1 1 calc R U . . .
C22 C 0.6200(3) 0.8409(7) 0.77560(14) 0.0970(12) Uani 1 1 d . . . . .
H22A H 0.6617 0.7679 0.8096 0.116 Uiso 1 1 calc R U . . .
H22B H 0.6154 1.0141 0.7819 0.116 Uiso 1 1 calc R U . . .
C23 C 0.5194(3) 0.7266(7) 0.76096(14) 0.0889(11) Uani 1 1 d . . . . .
H23A H 0.5088 0.6405 0.7930 0.107 Uiso 1 1 calc R U . . .
H23B H 0.4687 0.8486 0.7485 0.107 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 C1 1.748(3) . ?
S1 C16 1.776(3) . ?
N1 C2 1.365(3) . ?
N1 C3 1.374(3) . ?
N1 C9 1.467(3) . ?
N2 C16 1.329(3) . ?
N2 C18 1.347(4) . ?
C14 C15 1.348(6) . ?
C14 C12 1.405(6) . ?
C10 C11 1.369(4) . ?
C10 C12 1.374(4) . ?
C10 C9 1.515(4) . ?
C17 C16 1.378(4) . ?
C17 C20 1.385(3) . ?
C4 C5 1.399(4) . ?
C4 C3 1.409(4) . ?
C4 C1 1.429(4) . ?
C11 C13 1.373(4) . ?
C3 C8 1.387(4) . ?
C1 C2 1.364(4) . ?
C19 C18 1.361(4) . ?
C19 C20 1.373(4) . ?
C19 C23 1.507(4) . ?
C20 C21 1.501(4) . ?
C21 C22 1.527(4) . ?
C15 C13 1.338(5) . ?
C8 C7 1.369(4) . ?
C5 C6 1.369(4) . ?
C6 C7 1.403(4) . ?
C22 C23 1.510(5) . ?

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
C1 S1 C16 104.21(14) . . ?
C2 N1 C3 108.8(2) . . ?
C2 N1 C9 125.3(3) . . ?
C3 N1 C9 125.8(3) . . ?
C16 N2 C18 115.7(3) . . ?
C15 C14 C12 120.0(4) . . ?
C11 C10 C12 118.2(3) . . ?
C11 C10 C9 122.0(3) . . ?
C12 C10 C9 119.8(3) . . ?
C16 C17 C20 117.9(3) . . ?
C5 C4 C3 118.1(3) . . ?
C5 C4 C1 135.1(3) . . ?
C3 C4 C1 106.8(3) . . ?
N2 C16 C17 124.4(3) . . ?
N2 C16 S1 111.8(2) . . ?
C17 C16 S1 123.8(2) . . ?
C10 C11 C13 121.4(3) . . ?
N1 C3 C8 130.3(3) . . ?
N1 C3 C4 107.6(3) . . ?
C8 C3 C4 122.1(3) . . ?
C2 C1 C4 106.7(3) . . ?
C2 C1 S1 125.9(3) . . ?
C4 C1 S1 127.3(2) . . ?
C18 C19 C20 118.4(3) . . ?
C18 C19 C23 130.5(3) . . ?
C20 C19 C23 111.0(3) . . ?
C19 C20 C17 119.1(3) . . ?
C19 C20 C21 110.7(3) . . ?
C17 C20 C21 130.2(3) . . ?
C20 C21 C22 103.8(3) . . ?
C13 C15 C14 120.6(4) . . ?
C7 C8 C3 118.2(3) . . ?
C6 C5 C4 119.9(3) . . ?
N1 C9 C10 112.2(2) . . ?
C1 C2 N1 110.1(3) . . ?
C5 C6 C7 120.8(3) . . ?
N2 C18 C19 124.5(3) . . ?
C8 C7 C6 120.9(3) . . ?
C15 C13 C11 120.2(4) . . ?
C10 C12 C14 119.6(4) . . ?
C23 C22 C21 107.1(3) . . ?
C19 C23 C22 103.8(3) . . ?

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.041

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate - hexane'
####################################################################### 
# 
# 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_AG_HC_352
_audit_block_doi                 10.5517/ccdc.csd.cc1mwyr6
_database_code_depnum_ccdc_archive 'CCDC 1516419'
_audit_update_record             
;
2016-11-10 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        'Indole-C3-thio cyanide'
_chemical_name_common            'Indole-C3-thio cyanide'
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 N2 O S'
_chemical_formula_sum            'C17 H14 N2 O S'
_chemical_formula_weight         294.36

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.825(5)
_cell_length_b                   8.969(5)
_cell_length_c                   15.960(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 101.245(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1519.8(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3778
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      28.4

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      1.29
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.213
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6939
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean 10.233
_diffrn_reflns_number            63161
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.602
_diffrn_reflns_theta_max         28.351
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3778
_reflns_number_gt                2808
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'APEX2 (Bruker, 2014); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014);XPREP(Sheldrick,2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep, Pluton'
_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)+(0.0478P)²+0.4789P] 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       0.0086(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3778
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.95515(5) 0.09329(5) 0.35578(4) 0.0702(2) Uani 1 1 d . . . . .
O1 O 0.72412(13) 0.64496(17) 0.20597(9) 0.0741(4) Uani 1 1 d . . . . .
N1 N 1.12758(13) 0.45919(16) 0.44559(9) 0.0537(3) Uani 1 1 d . . . . .
C7 C 0.84476(15) 0.44486(18) 0.28648(11) 0.0497(4) Uani 1 1 d . . . . .
H7 H 0.7913 0.3705 0.2598 0.060 Uiso 1 1 calc R U . . .
C9 C 0.90288(18) 0.70503(18) 0.30668(11) 0.0565(4) Uani 1 1 d . . . . .
H9 H 0.8846 0.8040 0.2920 0.068 Uiso 1 1 calc R U . . .
C5 C 1.03038(15) 0.52371(16) 0.38796(10) 0.0464(4) Uani 1 1 d . . . . .
C8 C 0.82231(16) 0.59297(19) 0.26603(11) 0.0531(4) Uani 1 1 d . . . . .
C3 C 0.95055(14) 0.41032(15) 0.34861(10) 0.0455(4) Uani 1 1 d . . . . .
C11 C 1.33094(16) 0.58396(19) 0.44081(11) 0.0546(4) Uani 1 1 d . . . . .
C2 C 1.00375(17) 0.27417(17) 0.38604(12) 0.0528(4) Uani 1 1 d . . . . .
C6 C 1.00692(17) 0.67339(17) 0.36694(11) 0.0531(4) Uani 1 1 d . . . . .
H6 H 1.0602 0.7484 0.3930 0.064 Uiso 1 1 calc R U . . .
C10 C 1.23539(18) 0.5392(2) 0.49351(11) 0.0620(5) Uani 1 1 d . . . . .
H10A H 1.2765 0.4768 0.5404 0.074 Uiso 1 1 calc R U . . .
H10B H 1.2057 0.6281 0.5179 0.074 Uiso 1 1 calc R U . . .
C1 C 0.8396(2) 0.06439(19) 0.41131(14) 0.0676(5) Uani 1 1 d . . . . .
C4 C 1.11077(17) 0.30942(19) 0.44335(12) 0.0576(4) Uani 1 1 d . . . . .
H4 H 1.1641 0.2409 0.4760 0.069 Uiso 1 1 calc R U . . .
C13 C 1.41954(17) 0.6894(2) 0.47242(14) 0.0694(5) Uani 1 1 d . . . . .
H13 H 1.4187 0.7335 0.5251 0.083 Uiso 1 1 calc R U . . .
N2 N 0.7602(2) 0.0363(2) 0.44577(17) 0.1107(8) Uani 1 1 d . . . . .
C12 C 1.3333(2) 0.5206(3) 0.36244(14) 0.0800(6) Uani 1 1 d . . . . .
H12 H 1.2743 0.4483 0.3402 0.096 Uiso 1 1 calc R U . . .
C15 C 1.51017(19) 0.7307(3) 0.42656(19) 0.0870(7) Uani 1 1 d . . . . .
H15 H 1.5707 0.8012 0.4490 0.104 Uiso 1 1 calc R U . . .
C17 C 0.6484(2) 0.5380(3) 0.15440(16) 0.0922(7) Uani 1 1 d . . . . .
H17A H 0.5831 0.5879 0.1150 0.138 Uiso 1 1 calc R U . . .
H17B H 0.6995 0.4812 0.1232 0.138 Uiso 1 1 calc R U . . .
H17C H 0.6111 0.4723 0.1900 0.138 Uiso 1 1 calc R U . . .
C16 C 1.5112(2) 0.6690(3) 0.34902(18) 0.0920(8) Uani 1 1 d . . . . .
H16 H 1.5715 0.6980 0.3180 0.110 Uiso 1 1 calc R U . . .
C14 C 1.4234(2) 0.5644(3) 0.31680(17) 0.0986(8) Uani 1 1 d . . . . .
H14 H 1.4241 0.5221 0.2637 0.118 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 C1 1.688(2) . ?
S1 C2 1.7443(18) . ?
O1 C8 1.367(2) . ?
O1 C17 1.417(3) . ?
N1 C4 1.355(2) . ?
N1 C5 1.382(2) . ?
N1 C10 1.454(2) . ?
C7 C8 1.378(2) . ?
C7 C3 1.396(2) . ?
C9 C6 1.361(3) . ?
C9 C8 1.404(2) . ?
C5 C6 1.395(2) . ?
C5 C3 1.401(2) . ?
C3 C2 1.430(2) . ?
C11 C13 1.371(3) . ?
C11 C12 1.379(3) . ?
C11 C10 1.509(2) . ?
C2 C4 1.366(3) . ?
C1 N2 1.135(3) . ?
C13 C15 1.384(3) . ?
C12 C14 1.383(3) . ?
C15 C16 1.358(4) . ?
C16 C14 1.363(4) . ?

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
C1 S1 C2 102.22(8) . . ?
C8 O1 C17 117.33(17) . . ?
C4 N1 C5 108.46(15) . . ?
C4 N1 C10 126.36(16) . . ?
C5 N1 C10 124.92(15) . . ?
C8 C7 C3 117.68(15) . . ?
C6 C9 C8 122.10(15) . . ?
N1 C5 C6 129.95(15) . . ?
N1 C5 C3 108.50(14) . . ?
C6 C5 C3 121.55(16) . . ?
O1 C8 C7 124.88(16) . . ?
O1 C8 C9 114.07(16) . . ?
C7 C8 C9 121.05(17) . . ?
C7 C3 C5 120.41(14) . . ?
C7 C3 C2 133.95(15) . . ?
C5 C3 C2 105.64(15) . . ?
C13 C11 C12 118.87(18) . . ?
C13 C11 C10 118.99(17) . . ?
C12 C11 C10 122.12(17) . . ?
C4 C2 C3 107.57(14) . . ?
C4 C2 S1 124.85(14) . . ?
C3 C2 S1 127.11(15) . . ?
C9 C6 C5 117.22(15) . . ?
N1 C10 C11 113.90(14) . . ?
N2 C1 S1 175.5(2) . . ?
N1 C4 C2 109.82(16) . . ?
C11 C13 C15 120.5(2) . . ?
C11 C12 C14 120.0(2) . . ?
C16 C15 C13 120.3(2) . . ?
C15 C16 C14 119.7(2) . . ?
C16 C14 C12 120.5(2) . . ?

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.033

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate - Hexane'
####################################################################### 
# 
# 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_AG_HC_365
_audit_block_doi                 10.5517/ccdc.csd.cc1mwyq5
_database_code_depnum_ccdc_archive 'CCDC 1516418'
_audit_update_record             
;
2016-11-10 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        'Indole-C3-thio pyridine derivative2'
_chemical_name_common            'Indole-C3-thio pyridine derivative2'
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H30 N2 O2 S'
_chemical_formula_sum            'C31 H30 N2 O2 S'
_chemical_formula_weight         494.63

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.5208(9)
_cell_length_b                   12.0966(7)
_cell_length_c                   12.4375(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.984(2)
_cell_angle_gamma                90
_cell_volume                     2626.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6565
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      28.4

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      1.25
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6853
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean 10.233
_diffrn_reflns_number            56690
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.334
_diffrn_reflns_theta_max         28.363
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6565
_reflns_number_gt                4893
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'APEX2 (Bruker, 2014); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014);XPREP(Sheldrick,2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep, Pluton'
_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)+(0.0547P)²+1.1266P] 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         6565
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1400
_refine_ls_wR_factor_gt          0.1257
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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_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 0.38808(3) 0.60804(5) 0.34765(4) 0.05696(17) Uani 1 1 d . . . . .
O1 O -0.05502(11) 0.53444(17) 0.34532(18) 0.0922(6) Uani 1 1 d . . . . .
O2 O 0.06345(9) 0.83717(18) 0.47872(13) 0.0840(5) Uani 1 1 d . . . . .
N1 N 0.42807(8) 0.49528(13) 0.64198(11) 0.0417(3) Uani 1 1 d . . . . .
N2 N 0.27282(8) 0.68139(14) 0.22539(11) 0.0468(4) Uani 1 1 d . . . . .
C1 C -0.19183(15) 0.8788(3) 0.3160(2) 0.0926(9) Uani 1 1 d . . . . .
H27 H -0.2389 0.8385 0.3176 0.139 Uiso 1 1 calc R U . . .
H28 H -0.1834 0.8962 0.2427 0.139 Uiso 1 1 calc R U . . .
H1 H -0.1949 0.9460 0.3565 0.139 Uiso 1 1 calc R U . . .
C2 C -0.12510(11) 0.8081(2) 0.36613(16) 0.0618(6) Uani 1 1 d . . . . .
C3 C -0.11793(11) 0.7042(2) 0.29857(18) 0.0653(6) Uani 1 1 d . . . . .
H7 H -0.1643 0.6607 0.3009 0.078 Uiso 1 1 calc R U . . .
H6 H -0.1139 0.7257 0.2241 0.078 Uiso 1 1 calc R U . . .
C4 C -0.05013(11) 0.6334(2) 0.33544(17) 0.0580(5) Uani 1 1 d . . . . .
C5 C 0.02675(9) 0.69233(18) 0.35569(13) 0.0490(5) Uani 1 1 d . . . . .
C6 C 0.08848(10) 0.6218(2) 0.41911(15) 0.0592(6) Uani 1 1 d . . . . .
H25 H 0.0962 0.6460 0.4936 0.071 Uiso 1 1 calc R U . . .
H26 H 0.0741 0.5443 0.4176 0.071 Uiso 1 1 calc R U . . .
C7 C 0.15964(9) 0.64001(16) 0.36173(13) 0.0433(4) Uani 1 1 d . . . . .
C8 C 0.23455(9) 0.61243(16) 0.39408(13) 0.0431(4) Uani 1 1 d . . . . .
H24 H 0.2481 0.5802 0.4609 0.052 Uiso 1 1 calc R U . . .
C9 C 0.28888(9) 0.63511(15) 0.32192(13) 0.0404(4) Uani 1 1 d . . . . .
C10 C 0.39565(9) 0.53626(15) 0.46958(13) 0.0407(4) Uani 1 1 d . . . . .
C11 C 0.42137(9) 0.57969(15) 0.56773(14) 0.0402(4) Uani 1 1 d . . . . .
C12 C 0.44374(10) 0.50914(19) 0.75793(14) 0.0522(5) Uani 1 1 d . . . . .
H11 H 0.4799 0.5693 0.7715 0.063 Uiso 1 1 calc R U . . .
H12 H 0.4676 0.4423 0.7880 0.063 Uiso 1 1 calc R U . . .
C13 C 0.37287(10) 0.53327(15) 0.81524(14) 0.0430(4) Uani 1 1 d . . . . .
C14 C 0.38207(13) 0.56192(17) 0.92264(16) 0.0560(5) Uani 1 1 d . . . . .
H15 H 0.4311 0.5680 0.9573 0.067 Uiso 1 1 calc R U . . .
C15 C 0.31906(16) 0.5818(2) 0.97962(19) 0.0723(7) Uani 1 1 d . . . . .
H14 H 0.3259 0.6012 1.0522 0.087 Uiso 1 1 calc R U . . .
C16 C 0.24690(15) 0.57307(19) 0.9295(2) 0.0720(7) Uani 1 1 d . . . . .
H2 H 0.2046 0.5860 0.9681 0.086 Uiso 1 1 calc R U . . .
C17 C -0.13946(16) 0.7767(3) 0.4816(2) 0.0954(10) Uani 1 1 d . . . . .
H29 H -0.1854 0.7334 0.4809 0.143 Uiso 1 1 calc R U . . .
H3 H -0.1450 0.8425 0.5233 0.143 Uiso 1 1 calc R U . . .
H30 H -0.0969 0.7343 0.5133 0.143 Uiso 1 1 calc R U . . .
C18 C -0.05043(13) 0.8735(2) 0.36636(19) 0.0655(6) Uani 1 1 d . . . . .
H4 H -0.0437 0.8982 0.2936 0.079 Uiso 1 1 calc R U . . .
H5 H -0.0535 0.9385 0.4115 0.079 Uiso 1 1 calc R U . . .
C19 C 0.01772(10) 0.8051(2) 0.40757(15) 0.0557(5) Uani 1 1 d . . . . .
C20 C 0.05799(10) 0.7127(2) 0.24151(14) 0.0563(5) Uani 1 1 d . . . . .
H8 H 0.0340 0.6630 0.1875 0.068 Uiso 1 1 calc R U . . .
H9 H 0.0492 0.7884 0.2178 0.068 Uiso 1 1 calc R U . . .
C21 C 0.14212(9) 0.68894(16) 0.26233(13) 0.0435(4) Uani 1 1 d . . . . .
C22 C 0.20007(10) 0.70782(17) 0.19670(13) 0.0477(4) Uani 1 1 d . . . . .
H10 H 0.1880 0.7403 0.1296 0.057 Uiso 1 1 calc R U . . .
C23 C 0.29970(11) 0.52483(18) 0.76574(16) 0.0548(5) Uani 1 1 d . . . . .
H16 H 0.2925 0.5052 0.6933 0.066 Uiso 1 1 calc R U . . .
C24 C 0.23671(13) 0.54535(19) 0.8229(2) 0.0656(6) Uani 1 1 d . . . . .
H13 H 0.1875 0.5402 0.7886 0.079 Uiso 1 1 calc R U . . .
C25 C 0.40532(9) 0.39719(15) 0.59261(14) 0.0416(4) Uani 1 1 d . . . . .
C26 C 0.38442(9) 0.42021(15) 0.48360(14) 0.0412(4) Uani 1 1 d . . . . .
C27 C 0.35771(11) 0.3342(2) 0.41587(17) 0.0585(5) Uani 1 1 d . . . . .
H17 H 0.3429 0.3474 0.3434 0.070 Uiso 1 1 calc R U . . .
C28 C 0.35359(13) 0.2295(2) 0.4581(2) 0.0730(7) Uani 1 1 d . . . . .
H18 H 0.3352 0.1718 0.4137 0.088 Uiso 1 1 calc R U . . .
C29 C 0.37630(13) 0.2087(2) 0.5656(2) 0.0735(7) Uani 1 1 d . . . . .
H20 H 0.3742 0.1366 0.5913 0.088 Uiso 1 1 calc R U . . .
C30 C 0.40171(12) 0.29117(18) 0.63512(18) 0.0587(5) Uani 1 1 d . . . . .
H19 H 0.4159 0.2769 0.7076 0.070 Uiso 1 1 calc R U . . .
C31 C 0.43975(12) 0.69565(17) 0.59805(19) 0.0608(5) Uani 1 1 d . . . . .
H23 H 0.4382 0.7404 0.5341 0.091 Uiso 1 1 calc R U . . .
H22 H 0.4900 0.6990 0.6353 0.091 Uiso 1 1 calc R U . . .
H21 H 0.4029 0.7227 0.6444 0.091 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 C10 1.7424(17) . ?
S1 C9 1.7703(16) . ?
O1 C4 1.207(3) . ?
O2 C19 1.205(2) . ?
N1 C11 1.375(2) . ?
N1 C25 1.379(2) . ?
N1 C12 1.454(2) . ?
N2 C22 1.332(2) . ?
N2 C9 1.332(2) . ?
C1 C2 1.537(3) . ?
C1 H27 0.9600 . ?
C1 H28 0.9600 . ?
C1 H1 0.9600 . ?
C2 C3 1.523(3) . ?
C2 C17 1.528(3) . ?
C2 C18 1.529(3) . ?
C3 C4 1.504(3) . ?
C3 H7 0.9700 . ?
C3 H6 0.9700 . ?
C4 C5 1.526(3) . ?
C5 C19 1.523(3) . ?
C5 C6 1.540(3) . ?
C5 C20 1.585(2) . ?
C6 C7 1.506(2) . ?
C6 H25 0.9700 . ?
C6 H26 0.9700 . ?
C7 C8 1.380(2) . ?
C7 C21 1.381(2) . ?
C8 C9 1.391(2) . ?
C8 H24 0.9300 . ?
C10 C11 1.369(2) . ?
C10 C26 1.430(3) . ?
C11 C31 1.481(3) . ?
C12 C13 1.513(2) . ?
C12 H11 0.9700 . ?
C12 H12 0.9700 . ?
C13 C14 1.376(2) . ?
C13 C23 1.377(3) . ?
C14 C15 1.384(3) . ?
C14 H15 0.9300 . ?
C15 C16 1.364(4) . ?
C15 H14 0.9300 . ?
C16 C24 1.364(3) . ?
C16 H2 0.9300 . ?
C17 H29 0.9600 . ?
C17 H3 0.9600 . ?
C17 H30 0.9600 . ?
C18 C19 1.506(3) . ?
C18 H4 0.9700 . ?
C18 H5 0.9700 . ?
C20 C21 1.502(2) . ?
C20 H8 0.9700 . ?
C20 H9 0.9700 . ?
C21 C22 1.376(2) . ?
C22 H10 0.9300 . ?
C23 C24 1.386(3) . ?
C23 H16 0.9300 . ?
C24 H13 0.9300 . ?
C25 C30 1.391(3) . ?
C25 C26 1.401(2) . ?
C26 C27 1.394(3) . ?
C27 C28 1.376(4) . ?
C27 H17 0.9300 . ?
C28 C29 1.385(4) . ?
C28 H18 0.9300 . ?
C29 C30 1.369(3) . ?
C29 H20 0.9300 . ?
C30 H19 0.9300 . ?
C31 H23 0.9600 . ?
C31 H22 0.9600 . ?
C31 H21 0.9600 . ?

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
C10 S1 C9 104.41(8) . . ?
C11 N1 C25 109.60(14) . . ?
C11 N1 C12 125.33(16) . . ?
C25 N1 C12 124.28(16) . . ?
C22 N2 C9 117.66(14) . . ?
C2 C1 H27 109.5 . . ?
C2 C1 H28 109.5 . . ?
H27 C1 H28 109.5 . . ?
C2 C1 H1 109.5 . . ?
H27 C1 H1 109.5 . . ?
H28 C1 H1 109.5 . . ?
C3 C2 C17 110.0(2) . . ?
C3 C2 C18 108.45(17) . . ?
C17 C2 C18 109.7(2) . . ?
C3 C2 C1 109.39(19) . . ?
C17 C2 C1 109.8(2) . . ?
C18 C2 C1 109.5(2) . . ?
C4 C3 C2 113.76(17) . . ?
C4 C3 H7 108.8 . . ?
C2 C3 H7 108.8 . . ?
C4 C3 H6 108.8 . . ?
C2 C3 H6 108.8 . . ?
H7 C3 H6 107.7 . . ?
O1 C4 C3 122.4(2) . . ?
O1 C4 C5 121.1(2) . . ?
C3 C4 C5 116.5(2) . . ?
C19 C5 C4 111.47(16) . . ?
C19 C5 C6 111.92(16) . . ?
C4 C5 C6 113.35(18) . . ?
C19 C5 C20 107.27(17) . . ?
C4 C5 C20 107.07(15) . . ?
C6 C5 C20 105.26(14) . . ?
C7 C6 C5 104.47(15) . . ?
C7 C6 H25 110.9 . . ?
C5 C6 H25 110.9 . . ?
C7 C6 H26 110.9 . . ?
C5 C6 H26 110.9 . . ?
H25 C6 H26 108.9 . . ?
C8 C7 C21 119.77(15) . . ?
C8 C7 C6 129.22(15) . . ?
C21 C7 C6 110.99(15) . . ?
C7 C8 C9 116.81(15) . . ?
C7 C8 H24 121.6 . . ?
C9 C8 H24 121.6 . . ?
N2 C9 C8 124.16(15) . . ?
N2 C9 S1 111.58(12) . . ?
C8 C9 S1 124.26(13) . . ?
C11 C10 C26 107.82(15) . . ?
C11 C10 S1 125.39(15) . . ?
C26 C10 S1 126.46(13) . . ?
C10 C11 N1 108.44(16) . . ?
C10 C11 C31 129.66(18) . . ?
N1 C11 C31 121.90(16) . . ?
N1 C12 C13 113.42(15) . . ?
N1 C12 H11 108.9 . . ?
C13 C12 H11 108.9 . . ?
N1 C12 H12 108.9 . . ?
C13 C12 H12 108.9 . . ?
H11 C12 H12 107.7 . . ?
C14 C13 C23 118.60(17) . . ?
C14 C13 C12 118.31(17) . . ?
C23 C13 C12 123.06(16) . . ?
C13 C14 C15 120.6(2) . . ?
C13 C14 H15 119.7 . . ?
C15 C14 H15 119.7 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H14 119.9 . . ?
C14 C15 H14 119.9 . . ?
C15 C16 C24 120.0(2) . . ?
C15 C16 H2 120.0 . . ?
C24 C16 H2 120.0 . . ?
C2 C17 H29 109.5 . . ?
C2 C17 H3 109.5 . . ?
H29 C17 H3 109.5 . . ?
C2 C17 H30 109.5 . . ?
H29 C17 H30 109.5 . . ?
H3 C17 H30 109.5 . . ?
C19 C18 C2 111.7(2) . . ?
C19 C18 H4 109.3 . . ?
C2 C18 H4 109.3 . . ?
C19 C18 H5 109.3 . . ?
C2 C18 H5 109.3 . . ?
H4 C18 H5 107.9 . . ?
O2 C19 C18 122.0(2) . . ?
O2 C19 C5 120.8(2) . . ?
C18 C19 C5 117.16(16) . . ?
C21 C20 C5 103.06(13) . . ?
C21 C20 H8 111.2 . . ?
C5 C20 H8 111.2 . . ?
C21 C20 H9 111.2 . . ?
C5 C20 H9 111.2 . . ?
H8 C20 H9 109.1 . . ?
C22 C21 C7 118.96(15) . . ?
C22 C21 C20 129.02(15) . . ?
C7 C21 C20 112.01(15) . . ?
N2 C22 C21 122.64(15) . . ?
N2 C22 H10 118.7 . . ?
C21 C22 H10 118.7 . . ?
C13 C23 C24 120.6(2) . . ?
C13 C23 H16 119.7 . . ?
C24 C23 H16 119.7 . . ?
C16 C24 C23 120.0(2) . . ?
C16 C24 H13 120.0 . . ?
C23 C24 H13 120.0 . . ?
N1 C25 C30 130.18(17) . . ?
N1 C25 C26 107.52(15) . . ?
C30 C25 C26 122.30(18) . . ?
C27 C26 C25 118.84(18) . . ?
C27 C26 C10 134.54(18) . . ?
C25 C26 C10 106.61(15) . . ?
C28 C27 C26 118.8(2) . . ?
C28 C27 H17 120.6 . . ?
C26 C27 H17 120.6 . . ?
C27 C28 C29 121.1(2) . . ?
C27 C28 H18 119.5 . . ?
C29 C28 H18 119.5 . . ?
C30 C29 C28 121.8(2) . . ?
C30 C29 H20 119.1 . . ?
C28 C29 H20 119.1 . . ?
C29 C30 C25 117.1(2) . . ?
C29 C30 H19 121.5 . . ?
C25 C30 H19 121.5 . . ?
C11 C31 H23 109.5 . . ?
C11 C31 H22 109.5 . . ?
H23 C31 H22 109.5 . . ?
C11 C31 H21 109.5 . . ?
H23 C31 H21 109.5 . . ?
H22 C31 H21 109.5 . . ?

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
C17 C2 C3 C4 -64.1(2) . . . . ?
C18 C2 C3 C4 55.9(2) . . . . ?
C1 C2 C3 C4 175.3(2) . . . . ?
C2 C3 C4 O1 133.9(2) . . . . ?
C2 C3 C4 C5 -48.5(3) . . . . ?
O1 C4 C5 C19 -144.0(2) . . . . ?
C3 C4 C5 C19 38.3(2) . . . . ?
O1 C4 C5 C6 -16.7(3) . . . . ?
C3 C4 C5 C6 165.69(18) . . . . ?
O1 C4 C5 C20 98.9(2) . . . . ?
C3 C4 C5 C20 -78.7(2) . . . . ?
C19 C5 C6 C7 -96.21(18) . . . . ?
C4 C5 C6 C7 136.68(17) . . . . ?
C20 C5 C6 C7 20.0(2) . . . . ?
C5 C6 C7 C8 167.8(2) . . . . ?
C5 C6 C7 C21 -14.0(2) . . . . ?
C21 C7 C8 C9 -0.8(3) . . . . ?
C6 C7 C8 C9 177.3(2) . . . . ?
C22 N2 C9 C8 0.2(3) . . . . ?
C22 N2 C9 S1 -178.87(14) . . . . ?
C7 C8 C9 N2 0.2(3) . . . . ?
C7 C8 C9 S1 179.22(14) . . . . ?
C10 S1 C9 N2 -174.30(14) . . . . ?
C10 S1 C9 C8 6.59(19) . . . . ?
C9 S1 C10 C11 -103.79(15) . . . . ?
C9 S1 C10 C26 83.55(15) . . . . ?
C26 C10 C11 N1 1.14(17) . . . . ?
S1 C10 C11 N1 -172.67(11) . . . . ?
C26 C10 C11 C31 -178.23(16) . . . . ?
S1 C10 C11 C31 8.0(3) . . . . ?
C25 N1 C11 C10 -1.13(17) . . . . ?
C12 N1 C11 C10 -171.27(15) . . . . ?
C25 N1 C11 C31 178.31(15) . . . . ?
C12 N1 C11 C31 8.2(2) . . . . ?
C11 N1 C12 C13 83.7(2) . . . . ?
C25 N1 C12 C13 -85.1(2) . . . . ?
N1 C12 C13 C14 -171.76(18) . . . . ?
N1 C12 C13 C23 10.1(3) . . . . ?
C23 C13 C14 C15 0.0(3) . . . . ?
C12 C13 C14 C15 -178.2(2) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C14 C15 C16 C24 -0.4(4) . . . . ?
C3 C2 C18 C19 -56.7(2) . . . . ?
C17 C2 C18 C19 63.4(3) . . . . ?
C1 C2 C18 C19 -176.02(19) . . . . ?
C2 C18 C19 O2 -128.1(2) . . . . ?
C2 C18 C19 C5 51.7(2) . . . . ?
C4 C5 C19 O2 139.2(2) . . . . ?
C6 C5 C19 O2 11.1(3) . . . . ?
C20 C5 C19 O2 -103.9(2) . . . . ?
C4 C5 C19 C18 -40.6(2) . . . . ?
C6 C5 C19 C18 -168.68(17) . . . . ?
C20 C5 C19 C18 76.3(2) . . . . ?
C19 C5 C20 C21 100.39(18) . . . . ?
C4 C5 C20 C21 -139.85(18) . . . . ?
C6 C5 C20 C21 -19.0(2) . . . . ?
C8 C7 C21 C22 0.9(3) . . . . ?
C6 C7 C21 C22 -177.48(19) . . . . ?
C8 C7 C21 C20 179.98(18) . . . . ?
C6 C7 C21 C20 1.6(2) . . . . ?
C5 C20 C21 C22 -169.9(2) . . . . ?
C5 C20 C21 C7 11.1(2) . . . . ?
C9 N2 C22 C21 -0.1(3) . . . . ?
C7 C21 C22 N2 -0.4(3) . . . . ?
C20 C21 C22 N2 -179.3(2) . . . . ?
C14 C13 C23 C24 0.3(3) . . . . ?
C12 C13 C23 C24 178.4(2) . . . . ?
C15 C16 C24 C23 0.7(4) . . . . ?
C13 C23 C24 C16 -0.7(3) . . . . ?
C11 N1 C25 C30 -179.45(17) . . . . ?
C12 N1 C25 C30 -9.2(3) . . . . ?
C11 N1 C25 C26 0.65(17) . . . . ?
C12 N1 C25 C26 170.91(14) . . . . ?
N1 C25 C26 C27 -178.86(14) . . . . ?
C30 C25 C26 C27 1.2(2) . . . . ?
N1 C25 C26 C10 0.06(17) . . . . ?
C30 C25 C26 C10 -179.85(16) . . . . ?
C11 C10 C26 C27 177.93(18) . . . . ?
S1 C10 C26 C27 -8.3(3) . . . . ?
C11 C10 C26 C25 -0.74(17) . . . . ?
S1 C10 C26 C25 172.99(12) . . . . ?
C25 C26 C27 C28 -0.7(3) . . . . ?
C10 C26 C27 C28 -179.24(19) . . . . ?
C26 C27 C28 C29 -0.8(3) . . . . ?
C27 C28 C29 C30 1.9(4) . . . . ?
C28 C29 C30 C25 -1.3(3) . . . . ?
N1 C25 C30 C29 179.88(18) . . . . ?
C26 C25 C30 C29 -0.2(3) . . . . ?

_refine_diff_density_max         0.335
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.039

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate - hexane'
####################################################################### 
# 
# 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_AG-HC-382F
_audit_block_doi                 10.5517/ccdc.csd.cc1n5jzb
_database_code_depnum_ccdc_archive 'CCDC 1524672'
_audit_update_record             
;
2016-12-27 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        '3-thio Indole-derivative'
_chemical_name_common            '3-thio Indole-derivative'
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H22 N2 O S'
_chemical_formula_sum            'C28 H22 N2 O S'
_chemical_formula_weight         434.53

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'

_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                   10.1014(7)
_cell_length_b                   11.8755(8)
_cell_length_c                   19.3441(14)
_cell_angle_alpha                80.723(3)
_cell_angle_beta                 80.515(4)
_cell_angle_gamma                89.777(4)
_cell_volume                     2258.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    11246
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      28.4

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      1.28
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.166
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.5761
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean 10.233
_diffrn_reflns_number            56592
_diffrn_reflns_av_unetI/netI     0.1446
_diffrn_reflns_av_R_equivalents  0.1449
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.192
_diffrn_reflns_theta_max         28.447
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             11246
_reflns_number_gt                5322
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'APEX2 (Bruker, 2014); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014);XPREP(Sheldrick,2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep, Pluton'
_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)+(0.0858P)²+2.6848P] 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         11246
_refine_ls_number_parameters     577
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2438
_refine_ls_R_factor_gt           0.1196
_refine_ls_wR_factor_ref         0.2630
_refine_ls_wR_factor_gt          0.2170
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.018
_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_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 0.54167(14) 0.73390(10) 0.19588(7) 0.0534(4) Uani 1 1 d . . . . .
S2 S 0.04799(13) 0.66086(9) 0.19427(6) 0.0494(3) Uani 1 1 d . . . . .
O1 O 0.8541(4) 0.4824(4) 0.4316(2) 0.0851(12) Uani 1 1 d . . . . .
O2 O 0.3430(4) 0.7856(4) 0.4363(2) 0.0856(13) Uani 1 1 d . . . . .
N1 N 0.4680(3) 0.4588(3) 0.11921(18) 0.0382(8) Uani 1 1 d . . . . .
N2 N 0.6659(4) 0.7765(3) 0.29594(19) 0.0458(9) Uani 1 1 d . . . . .
C11 C 0.5931(4) 0.4865(3) 0.0793(2) 0.0342(9) Uani 1 1 d . . . . .
C10 C 0.6416(4) 0.5849(3) 0.0992(2) 0.0346(9) Uani 1 1 d . . . . .
N4 N -0.0349(3) 0.9754(3) 0.12035(19) 0.0383(8) Uani 1 1 d . . . . .
N3 N 0.1752(4) 0.5658(3) 0.29347(18) 0.0418(9) Uani 1 1 d . . . . .
C1 C 0.5253(6) 0.0465(5) 0.2249(3) 0.0723(17) Uani 1 1 d . . . . .
H1 H 0.5543 -0.0219 0.2476 0.087 Uiso 1 1 calc R U . . .
C2 C 0.4427(6) 0.0463(4) 0.1763(3) 0.0718(16) Uani 1 1 d . . . . .
H2 H 0.4152 -0.0226 0.1657 0.086 Uiso 1 1 calc R U . . .
C4 C 0.3997(6) 0.1464(4) 0.1428(3) 0.0636(14) Uani 1 1 d . . . . .
H4 H 0.3428 0.1448 0.1097 0.076 Uiso 1 1 calc R U . . .
C6 C 0.4395(4) 0.2501(3) 0.1573(2) 0.0423(11) Uani 1 1 d . . . . .
C7 C 0.3882(5) 0.3576(4) 0.1185(3) 0.0511(12) Uani 1 1 d . . . . .
H7A H 0.3877 0.3485 0.0696 0.061 Uiso 1 1 calc R U . . .
H7B H 0.2964 0.3684 0.1401 0.061 Uiso 1 1 calc R U . . .
C8 C 0.4382(4) 0.5361(3) 0.1636(2) 0.0399(10) Uani 1 1 d . . . . .
H8 H 0.3594 0.5355 0.1963 0.048 Uiso 1 1 calc R U . . .
C9 C 0.5398(4) 0.6148(3) 0.1537(2) 0.0403(10) Uani 1 1 d . . . . .
C16 C 0.6377(5) 0.6903(4) 0.2640(2) 0.0437(11) Uani 1 1 d . . . . .
C20 C 0.7408(5) 0.7587(4) 0.3480(2) 0.0470(11) Uani 1 1 d . . . . .
C23 C 0.7705(5) 0.8605(4) 0.3793(3) 0.0544(13) Uani 1 1 d . . . . .
C24 C 0.6740(7) 0.9397(5) 0.3912(3) 0.0787(18) Uani 1 1 d . . . . .
H24 H 0.5891 0.9288 0.3805 0.094 Uiso 1 1 calc R U . . .
C26 C 0.7013(8) 1.0356(5) 0.4191(4) 0.095(2) Uani 1 1 d . . . . .
H26 H 0.6344 1.0882 0.4273 0.114 Uiso 1 1 calc R U . . .
C25 C 0.8946(6) 0.8777(6) 0.3965(3) 0.0832(19) Uani 1 1 d . . . . .
H25 H 0.9611 0.8241 0.3901 0.100 Uiso 1 1 calc R U . . .
C19 C 0.7860(5) 0.6504(4) 0.3696(2) 0.0495(12) Uani 1 1 d . . . . .
C22 C 0.8670(5) 0.6020(5) 0.4255(3) 0.0642(15) Uani 1 1 d . . . . .
H22A H 0.9603 0.6266 0.4114 0.077 Uiso 1 1 calc R U . . .
H22B H 0.8324 0.6265 0.4704 0.077 Uiso 1 1 calc R U . . .
C21 C 0.8086(6) 0.4535(5) 0.3701(3) 0.0769(18) Uani 1 1 d . . . . .
H21A H 0.7402 0.3933 0.3836 0.092 Uiso 1 1 calc R U . . .
H21B H 0.8825 0.4284 0.3378 0.092 Uiso 1 1 calc R U . . .
C18 C 0.7523(5) 0.5613(4) 0.3366(2) 0.0496(12) Uani 1 1 d . . . . .
C17 C 0.6787(5) 0.5797(4) 0.2826(3) 0.0498(12) Uani 1 1 d . . . . .
H17 H 0.6572 0.5209 0.2596 0.060 Uiso 1 1 calc R U . . .
C12 C 0.6670(5) 0.4339(4) 0.0267(2) 0.0475(12) Uani 1 1 d . . . . .
H12 H 0.6345 0.3684 0.0138 0.057 Uiso 1 1 calc R U . . .
C13 C 0.7881(5) 0.4813(5) -0.0052(3) 0.0607(15) Uani 1 1 d . . . . .
H13 H 0.8385 0.4481 -0.0410 0.073 Uiso 1 1 calc R U . . .
C14 C 0.8393(5) 0.5781(5) 0.0141(3) 0.0632(15) Uani 1 1 d . . . . .
H14 H 0.9234 0.6075 -0.0084 0.076 Uiso 1 1 calc R U . . .
C15 C 0.7671(4) 0.6311(4) 0.0662(2) 0.0476(11) Uani 1 1 d . . . . .
H15 H 0.8013 0.6960 0.0789 0.057 Uiso 1 1 calc R U . . .
C3 C 0.5655(7) 0.1482(5) 0.2404(3) 0.086(2) Uani 1 1 d . . . . .
H3 H 0.6195 0.1488 0.2750 0.104 Uiso 1 1 calc R U . . .
C5 C 0.5255(5) 0.2513(4) 0.2043(3) 0.0590(14) Uani 1 1 d . . . . .
H5 H 0.5578 0.3203 0.2125 0.071 Uiso 1 1 calc R U . . .
C29 C 0.0253(6) 1.3394(5) 0.2180(3) 0.0701(16) Uani 1 1 d . . . . .
H29 H 0.0561 1.3973 0.2389 0.084 Uiso 1 1 calc R U . . .
C31 C 0.0680(7) 1.2287(5) 0.2337(3) 0.0839(19) Uani 1 1 d . . . . .
H31 H 0.1268 1.2112 0.2660 0.101 Uiso 1 1 calc R U . . .
C33 C 0.0237(6) 1.1467(4) 0.2021(3) 0.0629(15) Uani 1 1 d . . . . .
H33 H 0.0562 1.0735 0.2119 0.075 Uiso 1 1 calc R U . . .
C34 C -0.0663(4) 1.1653(3) 0.1565(2) 0.0425(11) Uani 1 1 d . . . . .
C35 C -0.1190(5) 1.0756(4) 0.1202(3) 0.0513(12) Uani 1 1 d . . . . .
H35A H -0.2091 1.0522 0.1441 0.062 Uiso 1 1 calc R U . . .
H35B H -0.1243 1.1085 0.0715 0.062 Uiso 1 1 calc R U . . .
C36 C -0.0623(4) 0.8741(3) 0.1638(2) 0.0405(10) Uani 1 1 d . . . . .
H36 H -0.1411 0.8561 0.1962 0.049 Uiso 1 1 calc R U . . .
C37 C 0.0419(4) 0.8023(3) 0.1533(2) 0.0391(10) Uani 1 1 d . . . . .
C45 C 0.1433(4) 0.6692(4) 0.2624(2) 0.0395(10) Uani 1 1 d . . . . .
C47 C 0.2473(4) 0.5564(4) 0.3468(2) 0.0433(11) Uani 1 1 d . . . . .
C52 C 0.2818(5) 0.4383(4) 0.3757(2) 0.0457(11) Uani 1 1 d . . . . .
C53 C 0.1943(7) 0.3497(5) 0.3771(3) 0.0795(18) Uani 1 1 d . . . . .
H53 H 0.1136 0.3649 0.3606 0.095 Uiso 1 1 calc R U . . .
C56 C 0.2232(8) 0.2379(5) 0.4026(4) 0.099(2) Uani 1 1 d . . . . .
H56 H 0.1635 0.1787 0.4022 0.119 Uiso 1 1 calc R U . . .
C57 C 0.3397(7) 0.2158(5) 0.4281(3) 0.0826(19) Uani 1 1 d . . . . .
H57 H 0.3608 0.1410 0.4445 0.099 Uiso 1 1 calc R U . . .
C30 C -0.0618(6) 1.3622(4) 0.1716(3) 0.0666(15) Uani 1 1 d . . . . .
H30 H -0.0912 1.4362 0.1605 0.080 Uiso 1 1 calc R U . . .
C32 C -0.1074(5) 1.2759(4) 0.1407(3) 0.0587(13) Uani 1 1 d . . . . .
H32 H -0.1668 1.2929 0.1087 0.070 Uiso 1 1 calc R U . . .
C38 C 0.0892(4) 0.9714(3) 0.0805(2) 0.0359(10) Uani 1 1 d . . . . .
C39 C 0.1413(4) 0.8636(3) 0.0994(2) 0.0342(9) Uani 1 1 d . . . . .
C41 C 0.2675(5) 0.8379(4) 0.0656(2) 0.0489(12) Uani 1 1 d . . . . .
H41 H 0.3037 0.7666 0.0773 0.059 Uiso 1 1 calc R U . . .
C42 C 0.3374(5) 0.9190(5) 0.0148(3) 0.0623(15) Uani 1 1 d . . . . .
H42 H 0.4218 0.9024 -0.0080 0.075 Uiso 1 1 calc R U . . .
C44 C 0.2847(5) 1.0265(5) -0.0035(3) 0.0611(15) Uani 1 1 d . . . . .
H44 H 0.3348 1.0801 -0.0382 0.073 Uiso 1 1 calc R U . . .
C40 C 0.1618(5) 1.0541(4) 0.0283(2) 0.0499(12) Uani 1 1 d . . . . .
H40 H 0.1268 1.1257 0.0160 0.060 Uiso 1 1 calc R U . . .
C46 C 0.1789(5) 0.7703(4) 0.2834(2) 0.0472(11) Uani 1 1 d . . . . .
H46 H 0.1557 0.8413 0.2613 0.057 Uiso 1 1 calc R U . . .
C49 C 0.2498(5) 0.7590(4) 0.3383(2) 0.0473(12) Uani 1 1 d . . . . .
C48 C 0.2860(4) 0.6532(4) 0.3704(2) 0.0461(11) Uani 1 1 d . . . . .
C55 C 0.4242(7) 0.3018(6) 0.4296(3) 0.0797(18) Uani 1 1 d . . . . .
H55 H 0.5023 0.2863 0.4486 0.096 Uiso 1 1 calc R U . . .
C54 C 0.3971(6) 0.4122(5) 0.4036(3) 0.0744(16) Uani 1 1 d . . . . .
H54 H 0.4575 0.4705 0.4049 0.089 Uiso 1 1 calc R U . . .
C51 C 0.3630(6) 0.6702(5) 0.4284(3) 0.0666(15) Uani 1 1 d . . . . .
H51A H 0.3284 0.6196 0.4723 0.080 Uiso 1 1 calc R U . . .
H51B H 0.4576 0.6559 0.4150 0.080 Uiso 1 1 calc R U . . .
C50 C 0.3001(6) 0.8483(5) 0.3759(3) 0.0747(17) Uani 1 1 d . . . . .
H50A H 0.3741 0.8929 0.3456 0.090 Uiso 1 1 calc R U . . .
H50B H 0.2289 0.8993 0.3897 0.090 Uiso 1 1 calc R U . . .
C28 C 0.8247(8) 1.0535(6) 0.4344(4) 0.087(2) Uani 1 1 d . . . . .
H28 H 0.8431 1.1188 0.4523 0.104 Uiso 1 1 calc R U . . .
C27 C 0.9207(7) 0.9763(7) 0.4238(4) 0.107(3) Uani 1 1 d . . . . .
H27 H 1.0053 0.9885 0.4346 0.129 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 1.745(4) . ?
S1 C16 1.772(5) . ?
S2 C37 1.744(4) . ?
S2 C45 1.770(5) . ?
O1 C22 1.412(6) . ?
O1 C21 1.433(7) . ?
O2 C50 1.411(7) . ?
O2 C51 1.413(6) . ?
N1 C8 1.357(5) . ?
N1 C11 1.379(5) . ?
N1 C7 1.452(5) . ?
N2 C16 1.333(5) . ?
N2 C20 1.346(6) . ?
C11 C12 1.391(6) . ?
C11 C10 1.402(5) . ?
C10 C15 1.394(6) . ?
C10 C9 1.434(6) . ?
N4 C36 1.353(5) . ?
N4 C38 1.365(5) . ?
N4 C35 1.459(5) . ?
N3 C45 1.340(5) . ?
N3 C47 1.349(5) . ?
C1 C2 1.357(8) . ?
C1 C3 1.368(8) . ?
C2 C4 1.364(7) . ?
C4 C6 1.382(6) . ?
C6 C5 1.359(6) . ?
C6 C7 1.508(6) . ?
C8 C9 1.360(6) . ?
C16 C17 1.385(6) . ?
C20 C19 1.386(6) . ?
C20 C23 1.489(6) . ?
C23 C24 1.369(7) . ?
C23 C25 1.373(8) . ?
C24 C26 1.383(8) . ?
C26 C28 1.353(9) . ?
C25 C27 1.402(8) . ?
C19 C18 1.391(7) . ?
C19 C22 1.502(7) . ?
C21 C18 1.494(7) . ?
C18 C17 1.369(7) . ?
C12 C13 1.356(7) . ?
C13 C14 1.390(7) . ?
C14 C15 1.379(7) . ?
C3 C5 1.401(7) . ?
C29 C30 1.354(8) . ?
C29 C31 1.384(8) . ?
C31 C33 1.345(7) . ?
C33 C34 1.362(6) . ?
C34 C32 1.378(6) . ?
C34 C35 1.510(6) . ?
C36 C37 1.362(6) . ?
C37 C39 1.428(6) . ?
C45 C46 1.395(6) . ?
C47 C48 1.383(6) . ?
C47 C52 1.485(6) . ?
C52 C53 1.370(7) . ?
C52 C54 1.377(7) . ?
C53 C56 1.388(8) . ?
C56 C57 1.357(8) . ?
C57 C55 1.341(8) . ?
C30 C32 1.382(7) . ?
C38 C39 1.399(5) . ?
C38 C40 1.400(6) . ?
C39 C41 1.391(6) . ?
C41 C42 1.365(7) . ?
C42 C44 1.396(7) . ?
C44 C40 1.356(7) . ?
C46 C49 1.364(6) . ?
C49 C48 1.385(6) . ?
C49 C50 1.512(7) . ?
C48 C51 1.506(7) . ?
C55 C54 1.370(8) . ?
C28 C27 1.346(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
C9 S1 C16 103.7(2) . . ?
C37 S2 C45 103.6(2) . . ?
C22 O1 C21 110.1(4) . . ?
C50 O2 C51 111.0(4) . . ?
C8 N1 C11 108.3(3) . . ?
C8 N1 C7 126.0(4) . . ?
C11 N1 C7 125.5(4) . . ?
C16 N2 C20 119.9(4) . . ?
N1 C11 C12 130.2(4) . . ?
N1 C11 C10 108.3(3) . . ?
C12 C11 C10 121.5(4) . . ?
C15 C10 C11 119.7(4) . . ?
C15 C10 C9 134.4(4) . . ?
C11 C10 C9 106.0(4) . . ?
C36 N4 C38 108.7(3) . . ?
C36 N4 C35 125.7(4) . . ?
C38 N4 C35 125.4(4) . . ?
C45 N3 C47 119.9(4) . . ?
C2 C1 C3 119.5(5) . . ?
C1 C2 C4 120.6(5) . . ?
C2 C4 C6 120.9(5) . . ?
C5 C6 C4 118.9(4) . . ?
C5 C6 C7 122.8(4) . . ?
C4 C6 C7 118.3(4) . . ?
N1 C7 C6 113.3(4) . . ?
N1 C8 C9 110.4(4) . . ?
C8 C9 C10 107.0(4) . . ?
C8 C9 S1 126.3(3) . . ?
C10 C9 S1 126.6(3) . . ?
N2 C16 C17 123.4(4) . . ?
N2 C16 S1 112.1(3) . . ?
C17 C16 S1 124.4(4) . . ?
N2 C20 C19 120.2(4) . . ?
N2 C20 C23 116.2(4) . . ?
C19 C20 C23 123.6(5) . . ?
C24 C23 C25 118.5(5) . . ?
C24 C23 C20 120.4(5) . . ?
C25 C23 C20 121.1(5) . . ?
C23 C24 C26 120.9(6) . . ?
C28 C26 C24 120.4(6) . . ?
C23 C25 C27 119.7(6) . . ?
C20 C19 C18 118.7(5) . . ?
C20 C19 C22 133.5(5) . . ?
C18 C19 C22 107.7(4) . . ?
O1 C22 C19 105.5(4) . . ?
O1 C21 C18 104.7(4) . . ?
C17 C18 C19 121.2(4) . . ?
C17 C18 C21 130.0(5) . . ?
C19 C18 C21 108.8(5) . . ?
C18 C17 C16 116.5(4) . . ?
C13 C12 C11 117.6(5) . . ?
C12 C13 C14 122.0(5) . . ?
C15 C14 C13 121.0(5) . . ?
C14 C15 C10 118.2(5) . . ?
C1 C3 C5 120.1(6) . . ?
C6 C5 C3 119.9(5) . . ?
C30 C29 C31 118.9(5) . . ?
C33 C31 C29 119.6(6) . . ?
C31 C33 C34 123.4(5) . . ?
C33 C34 C32 116.6(4) . . ?
C33 C34 C35 125.0(4) . . ?
C32 C34 C35 118.3(4) . . ?
N4 C35 C34 112.7(4) . . ?
N4 C36 C37 110.2(4) . . ?
C36 C37 C39 106.6(4) . . ?
C36 C37 S2 126.4(3) . . ?
C39 C37 S2 126.9(3) . . ?
N3 C45 C46 123.1(4) . . ?
N3 C45 S2 112.0(3) . . ?
C46 C45 S2 124.9(4) . . ?
N3 C47 C48 120.0(4) . . ?
N3 C47 C52 115.6(4) . . ?
C48 C47 C52 124.4(4) . . ?
C53 C52 C54 117.1(5) . . ?
C53 C52 C47 119.6(5) . . ?
C54 C52 C47 123.3(5) . . ?
C52 C53 C56 121.6(6) . . ?
C57 C56 C53 119.3(6) . . ?
C55 C57 C56 120.0(6) . . ?
C29 C30 C32 120.3(5) . . ?
C34 C32 C30 121.1(5) . . ?
N4 C38 C39 108.2(3) . . ?
N4 C38 C40 130.4(4) . . ?
C39 C38 C40 121.4(4) . . ?
C41 C39 C38 119.3(4) . . ?
C41 C39 C37 134.4(4) . . ?
C38 C39 C37 106.3(4) . . ?
C42 C41 C39 118.9(5) . . ?
C41 C42 C44 121.4(5) . . ?
C40 C44 C42 121.2(5) . . ?
C44 C40 C38 117.9(4) . . ?
C49 C46 C45 116.2(4) . . ?
C46 C49 C48 121.7(4) . . ?
C46 C49 C50 130.4(5) . . ?
C48 C49 C50 107.9(5) . . ?
C47 C48 C49 119.0(4) . . ?
C47 C48 C51 132.4(5) . . ?
C49 C48 C51 108.6(4) . . ?
C57 C55 C54 121.0(6) . . ?
C55 C54 C52 121.0(6) . . ?
O2 C51 C48 104.4(4) . . ?
O2 C50 C49 104.7(4) . . ?
C27 C28 C26 119.8(6) . . ?
C28 C27 C25 120.7(6) . . ?

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
C8 N1 C11 C12 -179.8(4) . . . . ?
C7 N1 C11 C12 5.8(6) . . . . ?
C8 N1 C11 C10 -0.6(4) . . . . ?
C7 N1 C11 C10 -175.0(4) . . . . ?
N1 C11 C10 C15 -179.7(3) . . . . ?
C12 C11 C10 C15 -0.4(6) . . . . ?
N1 C11 C10 C9 0.4(4) . . . . ?
C12 C11 C10 C9 179.7(4) . . . . ?
C3 C1 C2 C4 0.0(9) . . . . ?
C1 C2 C4 C6 0.3(9) . . . . ?
C2 C4 C6 C5 1.8(8) . . . . ?
C2 C4 C6 C7 -179.9(5) . . . . ?
C8 N1 C7 C6 -98.9(5) . . . . ?
C11 N1 C7 C6 74.6(5) . . . . ?
C5 C6 C7 N1 17.5(7) . . . . ?
C4 C6 C7 N1 -160.7(4) . . . . ?
C11 N1 C8 C9 0.5(5) . . . . ?
C7 N1 C8 C9 174.9(4) . . . . ?
N1 C8 C9 C10 -0.2(5) . . . . ?
N1 C8 C9 S1 176.6(3) . . . . ?
C15 C10 C9 C8 -179.9(4) . . . . ?
C11 C10 C9 C8 -0.2(4) . . . . ?
C15 C10 C9 S1 3.3(7) . . . . ?
C11 C10 C9 S1 -176.9(3) . . . . ?
C16 S1 C9 C8 100.1(4) . . . . ?
C16 S1 C9 C10 -83.8(4) . . . . ?
C20 N2 C16 C17 1.8(6) . . . . ?
C20 N2 C16 S1 -178.6(3) . . . . ?
C9 S1 C16 N2 171.2(3) . . . . ?
C9 S1 C16 C17 -9.2(4) . . . . ?
C16 N2 C20 C19 -1.6(6) . . . . ?
C16 N2 C20 C23 178.4(4) . . . . ?
N2 C20 C23 C24 39.5(7) . . . . ?
C19 C20 C23 C24 -140.6(5) . . . . ?
N2 C20 C23 C25 -140.1(5) . . . . ?
C19 C20 C23 C25 39.8(7) . . . . ?
C25 C23 C24 C26 0.8(9) . . . . ?
C20 C23 C24 C26 -178.8(6) . . . . ?
C23 C24 C26 C28 0.6(10) . . . . ?
C24 C23 C25 C27 -1.7(9) . . . . ?
C20 C23 C25 C27 178.0(6) . . . . ?
N2 C20 C19 C18 0.0(6) . . . . ?
C23 C20 C19 C18 -180.0(4) . . . . ?
N2 C20 C19 C22 -178.6(5) . . . . ?
C23 C20 C19 C22 1.5(8) . . . . ?
C21 O1 C22 C19 18.1(5) . . . . ?
C20 C19 C22 O1 167.5(5) . . . . ?
C18 C19 C22 O1 -11.2(5) . . . . ?
C22 O1 C21 C18 -17.6(6) . . . . ?
C20 C19 C18 C17 1.5(7) . . . . ?
C22 C19 C18 C17 -179.6(4) . . . . ?
C20 C19 C18 C21 -178.4(4) . . . . ?
C22 C19 C18 C21 0.5(5) . . . . ?
O1 C21 C18 C17 -169.7(5) . . . . ?
O1 C21 C18 C19 10.1(6) . . . . ?
C19 C18 C17 C16 -1.3(7) . . . . ?
C21 C18 C17 C16 178.6(5) . . . . ?
N2 C16 C17 C18 -0.4(7) . . . . ?
S1 C16 C17 C18 -180.0(3) . . . . ?
N1 C11 C12 C13 178.9(4) . . . . ?
C10 C11 C12 C13 -0.3(6) . . . . ?
C11 C12 C13 C14 1.0(7) . . . . ?
C12 C13 C14 C15 -1.0(8) . . . . ?
C13 C14 C15 C10 0.2(7) . . . . ?
C11 C10 C15 C14 0.5(6) . . . . ?
C9 C10 C15 C14 -179.8(4) . . . . ?
C2 C1 C3 C5 -2.3(10) . . . . ?
C4 C6 C5 C3 -4.0(8) . . . . ?
C7 C6 C5 C3 177.7(5) . . . . ?
C1 C3 C5 C6 4.4(9) . . . . ?
C30 C29 C31 C33 0.9(10) . . . . ?
C29 C31 C33 C34 -2.5(10) . . . . ?
C31 C33 C34 C32 2.9(9) . . . . ?
C31 C33 C34 C35 -179.7(6) . . . . ?
C36 N4 C35 C34 102.6(5) . . . . ?
C38 N4 C35 C34 -71.9(5) . . . . ?
C33 C34 C35 N4 -18.2(7) . . . . ?
C32 C34 C35 N4 159.1(4) . . . . ?
C38 N4 C36 C37 -0.2(5) . . . . ?
C35 N4 C36 C37 -175.5(4) . . . . ?
N4 C36 C37 C39 0.0(5) . . . . ?
N4 C36 C37 S2 -176.7(3) . . . . ?
C45 S2 C37 C36 -100.2(4) . . . . ?
C45 S2 C37 C39 83.7(4) . . . . ?
C47 N3 C45 C46 -1.3(6) . . . . ?
C47 N3 C45 S2 -179.7(3) . . . . ?
C37 S2 C45 N3 -171.0(3) . . . . ?
C37 S2 C45 C46 10.7(4) . . . . ?
C45 N3 C47 C48 1.3(6) . . . . ?
C45 N3 C47 C52 -177.7(4) . . . . ?
N3 C47 C52 C53 -32.9(6) . . . . ?
C48 C47 C52 C53 148.2(5) . . . . ?
N3 C47 C52 C54 149.1(5) . . . . ?
C48 C47 C52 C54 -29.8(7) . . . . ?
C54 C52 C53 C56 -2.9(9) . . . . ?
C47 C52 C53 C56 179.0(6) . . . . ?
C52 C53 C56 C57 1.4(11) . . . . ?
C53 C56 C57 C55 1.2(11) . . . . ?
C31 C29 C30 C32 0.1(9) . . . . ?
C33 C34 C32 C30 -1.9(8) . . . . ?
C35 C34 C32 C30 -179.4(5) . . . . ?
C29 C30 C32 C34 0.4(9) . . . . ?
C36 N4 C38 C39 0.2(4) . . . . ?
C35 N4 C38 C39 175.6(4) . . . . ?
C36 N4 C38 C40 -180.0(4) . . . . ?
C35 N4 C38 C40 -4.6(7) . . . . ?
N4 C38 C39 C41 179.6(4) . . . . ?
C40 C38 C39 C41 -0.2(6) . . . . ?
N4 C38 C39 C37 -0.2(4) . . . . ?
C40 C38 C39 C37 180.0(4) . . . . ?
C36 C37 C39 C41 -179.6(5) . . . . ?
S2 C37 C39 C41 -2.9(7) . . . . ?
C36 C37 C39 C38 0.1(5) . . . . ?
S2 C37 C39 C38 176.8(3) . . . . ?
C38 C39 C41 C42 0.2(6) . . . . ?
C37 C39 C41 C42 179.9(5) . . . . ?
C39 C41 C42 C44 0.0(7) . . . . ?
C41 C42 C44 C40 -0.2(8) . . . . ?
C42 C44 C40 C38 0.2(7) . . . . ?
N4 C38 C40 C44 -179.7(4) . . . . ?
C39 C38 C40 C44 0.1(6) . . . . ?
N3 C45 C46 C49 0.2(6) . . . . ?
S2 C45 C46 C49 178.4(3) . . . . ?
C45 C46 C49 C48 1.0(6) . . . . ?
C45 C46 C49 C50 -177.7(5) . . . . ?
N3 C47 C48 C49 -0.2(6) . . . . ?
C52 C47 C48 C49 178.8(4) . . . . ?
N3 C47 C48 C51 178.7(5) . . . . ?
C52 C47 C48 C51 -2.4(8) . . . . ?
C46 C49 C48 C47 -1.0(7) . . . . ?
C50 C49 C48 C47 177.9(4) . . . . ?
C46 C49 C48 C51 179.9(4) . . . . ?
C50 C49 C48 C51 -1.2(5) . . . . ?
C56 C57 C55 C54 -2.1(11) . . . . ?
C57 C55 C54 C52 0.5(10) . . . . ?
C53 C52 C54 C55 1.9(8) . . . . ?
C47 C52 C54 C55 180.0(5) . . . . ?
C50 O2 C51 C48 -18.8(6) . . . . ?
C47 C48 C51 O2 -167.1(5) . . . . ?
C49 C48 C51 O2 11.8(5) . . . . ?
C51 O2 C50 C49 18.1(6) . . . . ?
C46 C49 C50 O2 168.9(5) . . . . ?
C48 C49 C50 O2 -9.9(6) . . . . ?
C24 C26 C28 C27 -1.2(11) . . . . ?
C26 C28 C27 C25 0.4(12) . . . . ?
C23 C25 C27 C28 1.1(11) . . . . ?

_refine_diff_density_max         0.430
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.069

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Eyhyl acetate - hexane'
