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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_mo_d8v17287_0m
_database_code_depnum_ccdc_archive 'CCDC 1878309'
_audit_update_record             
;
2018-11-11 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 N2 O S'
_chemical_formula_weight         386.49

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.4030(5)
_cell_length_b                   7.0095(3)
_cell_length_c                   12.9123(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.0273(13)
_cell_angle_gamma                90
_cell_volume                     1031.91(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      4.704
_cell_measurement_theta_max      54.309

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.173
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6543
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19690
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.156
_diffrn_reflns_theta_max         25.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3804
_reflns_number_gt                3504
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.826
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.981

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0652P)²+0.0367P] 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       0.022(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1464 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.00(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3804
_refine_ls_number_parameters     256
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.002
_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 0.62280(5) 0.34529(10) 0.96863(4) 0.0514(2) Uani 1 1 d . . . . .
N1 N 0.77106(16) 0.1953(3) 0.74649(15) 0.0435(5) Uani 1 1 d . . . . .
N2 N 0.66728(16) 0.0857(3) 0.73788(15) 0.0438(5) Uani 1 1 d . . . . .
O1 O 0.82720(16) 0.4896(3) 0.81026(15) 0.0571(5) Uani 1 1 d . . . . .
C1 C 0.75469(19) 0.3654(4) 0.79472(17) 0.0436(5) Uani 1 1 d . . . . .
C2 C 0.62617(19) 0.3645(4) 0.82606(16) 0.0417(5) Uani 1 1 d . . . . .
C3 C 0.5843(2) 0.1813(4) 0.77914(18) 0.0414(5) Uani 1 1 d . . . . .
C4 C 0.4627(2) 0.1036(4) 0.7824(2) 0.0557(7) Uani 1 1 d . . . . .
H4A H 0.4132 0.1730 0.7347 0.083 Uiso 1 1 calc R U . . .
H4B H 0.4332 0.1167 0.8511 0.083 Uiso 1 1 calc R U . . .
H4C H 0.4635 -0.0288 0.7634 0.083 Uiso 1 1 calc R U . . .
C5 C 0.5612(2) 0.5545(4) 0.8008(2) 0.0486(6) Uani 1 1 d . . . . .
H5A H 0.5137 0.5879 0.8597 0.058 Uiso 1 1 calc R U . . .
H5B H 0.6195 0.6541 0.7932 0.058 Uiso 1 1 calc R U . . .
C6 C 0.4825(2) 0.5542(4) 0.70431(19) 0.0482(6) Uani 1 1 d . . . . .
C7 C 0.3614(3) 0.5527(5) 0.7198(2) 0.0616(7) Uani 1 1 d . . . . .
H7 H 0.3331 0.5528 0.7869 0.074 Uiso 1 1 calc R U . . .
C8 C 0.2828(3) 0.5509(6) 0.6365(3) 0.0739(9) Uani 1 1 d . . . . .
H8 H 0.2025 0.5502 0.6475 0.089 Uiso 1 1 calc R U . . .
C9 C 0.3246(3) 0.5501(6) 0.5387(3) 0.0814(10) Uani 1 1 d . . . . .
H9 H 0.2726 0.5466 0.4825 0.098 Uiso 1 1 calc R U . . .
C10 C 0.4418(3) 0.5543(6) 0.5225(2) 0.0781(9) Uani 1 1 d . . . . .
H10 H 0.4683 0.5553 0.4549 0.094 Uiso 1 1 calc R U . . .
C11 C 0.5242(3) 0.5572(4) 0.6042(2) 0.0584(7) Uani 1 1 d . . . . .
C12 C 0.6524(3) 0.5641(7) 0.5817(3) 0.0821(10) Uani 1 1 d . . . . .
H12A H 0.6631 0.6070 0.5119 0.123 Uiso 1 1 calc R U . . .
H12B H 0.6855 0.4390 0.5899 0.123 Uiso 1 1 calc R U . . .
H12C H 0.6908 0.6506 0.6289 0.123 Uiso 1 1 calc R U . . .
C13 C 0.8764(2) 0.1189(4) 0.7059(2) 0.0487(6) Uani 1 1 d . . . . .
C14 C 0.9513(3) 0.2342(5) 0.6524(3) 0.0819(10) Uani 1 1 d . . . . .
H14 H 0.9345 0.3629 0.6430 0.098 Uiso 1 1 calc R U . . .
C15 C 1.0524(4) 0.1558(7) 0.6128(4) 0.1035(15) Uani 1 1 d . . . . .
H15 H 1.1038 0.2328 0.5765 0.124 Uiso 1 1 calc R U . . .
C16 C 1.0776(4) -0.0329(7) 0.6263(4) 0.1061(16) Uani 1 1 d . . . . .
H16 H 1.1466 -0.0839 0.6007 0.127 Uiso 1 1 calc R U . . .
C17 C 1.0003(3) -0.1465(7) 0.6777(4) 0.0998(13) Uani 1 1 d . . . . .
H17 H 1.0163 -0.2758 0.6856 0.120 Uiso 1 1 calc R U . . .
C18 C 0.8998(3) -0.0723(5) 0.7177(3) 0.0729(9) Uani 1 1 d . . . . .
H18 H 0.8478 -0.1506 0.7525 0.087 Uiso 1 1 calc R U . . .
C19 C 0.7286(2) 0.1679(4) 1.00039(18) 0.0454(6) Uani 1 1 d . . . . .
C20 C 0.7043(3) -0.0237(4) 0.9887(2) 0.0537(6) Uani 1 1 d . . . . .
H20 H 0.6334 -0.0619 0.9587 0.064 Uiso 1 1 calc R U . . .
C21 C 0.7847(3) -0.1590(5) 1.0211(2) 0.0729(8) Uani 1 1 d . . . . .
H21 H 0.7685 -0.2881 1.0123 0.087 Uiso 1 1 calc R U . . .
C22 C 0.8895(3) -0.1020(6) 1.0668(3) 0.0739(9) Uani 1 1 d . . . . .
H22 H 0.9436 -0.1929 1.0894 0.089 Uiso 1 1 calc R U . . .
C23 C 0.9137(3) 0.0881(6) 1.0790(3) 0.0761(10) Uani 1 1 d . . . . .
H23 H 0.9839 0.1258 1.1105 0.091 Uiso 1 1 calc R U . . .
C24 C 0.8348(3) 0.2235(5) 1.0448(2) 0.0614(7) Uani 1 1 d . . . . .
H24 H 0.8527 0.3524 1.0516 0.074 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 C19 1.776(3) . ?
S1 C2 1.847(2) . ?
N1 C1 1.360(3) . ?
N1 N2 1.414(3) . ?
N1 C13 1.423(3) . ?
N2 C3 1.283(3) . ?
O1 C1 1.215(3) . ?
C1 C2 1.527(3) . ?
C2 C3 1.494(4) . ?
C2 C5 1.556(4) . ?
C3 C4 1.491(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.522(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C11 1.385(4) . ?
C6 C7 1.399(4) . ?
C7 C8 1.388(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.357(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.356(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.400(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.496(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C18 1.374(4) . ?
C13 C14 1.372(4) . ?
C14 C15 1.383(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.364(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.368(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.368(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.379(4) . ?
C19 C24 1.386(4) . ?
C20 C21 1.379(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.382(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.370(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.375(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

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
C19 S1 C2 104.78(11) . . ?
C1 N1 N2 113.03(19) . . ?
C1 N1 C13 128.5(2) . . ?
N2 N1 C13 118.5(2) . . ?
C3 N2 N1 107.8(2) . . ?
O1 C1 N1 127.3(2) . . ?
O1 C1 C2 127.8(2) . . ?
N1 C1 C2 105.0(2) . . ?
C3 C2 C1 101.38(19) . . ?
C3 C2 C5 120.19(17) . . ?
C1 C2 C5 113.4(2) . . ?
C3 C2 S1 109.22(17) . . ?
C1 C2 S1 107.55(14) . . ?
C5 C2 S1 104.67(15) . . ?
N2 C3 C4 120.9(2) . . ?
N2 C3 C2 112.6(2) . . ?
C4 C3 C2 126.4(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C2 116.3(2) . . ?
C6 C5 H5A 108.2 . . ?
C2 C5 H5A 108.2 . . ?
C6 C5 H5B 108.2 . . ?
C2 C5 H5B 108.2 . . ?
H5A C5 H5B 107.4 . . ?
C11 C6 C7 119.3(2) . . ?
C11 C6 C5 123.8(2) . . ?
C7 C6 C5 116.9(2) . . ?
C8 C7 C6 121.0(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C9 C8 C7 119.2(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 120.4(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C11 122.3(3) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C6 C11 C10 117.8(3) . . ?
C6 C11 C12 122.3(3) . . ?
C10 C11 C12 119.9(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 120.6(3) . . ?
C18 C13 N1 119.3(3) . . ?
C14 C13 N1 120.0(3) . . ?
C13 C14 C15 118.8(4) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 120.9(4) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 119.3(4) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 120.9(4) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C13 119.4(3) . . ?
C17 C18 H18 120.3 . . ?
C13 C18 H18 120.3 . . ?
C20 C19 C24 119.4(3) . . ?
C20 C19 S1 121.5(2) . . ?
C24 C19 S1 118.9(2) . . ?
C19 C20 C21 120.3(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C22 119.7(3) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C23 C22 C21 120.1(3) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C22 120.4(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C19 120.0(3) . . ?
C23 C24 H24 120.0 . . ?
C19 C24 H24 120.0 . . ?

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
C1 N1 N2 C3 0.2(3) . . . . ?
C13 N1 N2 C3 -180.0(2) . . . . ?
N2 N1 C1 O1 -177.9(2) . . . . ?
C13 N1 C1 O1 2.3(4) . . . . ?
N2 N1 C1 C2 2.8(2) . . . . ?
C13 N1 C1 C2 -177.0(2) . . . . ?
O1 C1 C2 C3 176.5(2) . . . . ?
N1 C1 C2 C3 -4.2(2) . . . . ?
O1 C1 C2 C5 46.3(3) . . . . ?
N1 C1 C2 C5 -134.4(2) . . . . ?
O1 C1 C2 S1 -68.9(3) . . . . ?
N1 C1 C2 S1 110.35(18) . . . . ?
C19 S1 C2 C3 65.32(18) . . . . ?
C19 S1 C2 C1 -43.9(2) . . . . ?
C19 S1 C2 C5 -164.74(16) . . . . ?
N1 N2 C3 C4 180.0(2) . . . . ?
N1 N2 C3 C2 -3.3(3) . . . . ?
C1 C2 C3 N2 4.7(2) . . . . ?
C5 C2 C3 N2 130.5(2) . . . . ?
S1 C2 C3 N2 -108.6(2) . . . . ?
C1 C2 C3 C4 -178.7(2) . . . . ?
C5 C2 C3 C4 -52.9(3) . . . . ?
S1 C2 C3 C4 67.9(3) . . . . ?
C3 C2 C5 C6 -18.6(3) . . . . ?
C1 C2 C5 C6 101.4(3) . . . . ?
S1 C2 C5 C6 -141.7(2) . . . . ?
C2 C5 C6 C11 -73.8(3) . . . . ?
C2 C5 C6 C7 106.8(3) . . . . ?
C11 C6 C7 C8 1.1(5) . . . . ?
C5 C6 C7 C8 -179.5(3) . . . . ?
C6 C7 C8 C9 0.2(5) . . . . ?
C7 C8 C9 C10 -1.1(6) . . . . ?
C8 C9 C10 C11 0.8(6) . . . . ?
C7 C6 C11 C10 -1.4(4) . . . . ?
C5 C6 C11 C10 179.3(3) . . . . ?
C7 C6 C11 C12 178.4(3) . . . . ?
C5 C6 C11 C12 -1.0(5) . . . . ?
C9 C10 C11 C6 0.5(5) . . . . ?
C9 C10 C11 C12 -179.3(4) . . . . ?
C1 N1 C13 C18 140.6(3) . . . . ?
N2 N1 C13 C18 -39.1(4) . . . . ?
C1 N1 C13 C14 -41.7(4) . . . . ?
N2 N1 C13 C14 138.5(3) . . . . ?
C18 C13 C14 C15 -1.6(6) . . . . ?
N1 C13 C14 C15 -179.3(4) . . . . ?
C13 C14 C15 C16 0.1(8) . . . . ?
C14 C15 C16 C17 1.5(9) . . . . ?
C15 C16 C17 C18 -1.5(8) . . . . ?
C16 C17 C18 C13 0.0(7) . . . . ?
C14 C13 C18 C17 1.6(6) . . . . ?
N1 C13 C18 C17 179.2(3) . . . . ?
C2 S1 C19 C20 -78.5(2) . . . . ?
C2 S1 C19 C24 106.1(2) . . . . ?
C24 C19 C20 C21 0.2(4) . . . . ?
S1 C19 C20 C21 -175.1(2) . . . . ?
C19 C20 C21 C22 0.8(5) . . . . ?
C20 C21 C22 C23 -0.6(5) . . . . ?
C21 C22 C23 C24 -0.7(6) . . . . ?
C22 C23 C24 C19 1.8(5) . . . . ?
C20 C19 C24 C23 -1.5(4) . . . . ?
S1 C19 C24 C23 173.9(3) . . . . ?

_refine_diff_density_max         0.128
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.025

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_d8v17770_0m
_database_code_depnum_ccdc_archive 'CCDC 1878310'
_audit_update_record             
;
2018-11-11 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H24 N2 O2 S'
_chemical_formula_weight         464.56

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.2478(2)
_cell_length_b                   8.1523(2)
_cell_length_c                   28.2987(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.4810(10)
_cell_angle_gamma                90
_cell_volume                     2359.80(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9874
_cell_measurement_theta_min      5.201
_cell_measurement_theta_max      54.950

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.167
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5383
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38624
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.991
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             9155
_reflns_number_gt                8410
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.848
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    0.980

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0495P)²+0.3805P] 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_abs_structure_details 
; 
 Flack x determined using 3546 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.05(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         9155
_refine_ls_number_parameters     615
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0986
_refine_ls_wR_factor_gt          0.0945
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.003
_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
N1 N 0.24781(19) 0.6269(4) 0.36933(7) 0.0273(5) Uani 1 1 d . . . . .
N2 N 0.1429(2) 0.5205(3) 0.35587(8) 0.0294(5) Uani 1 1 d . . . . .
N3 N 0.2471(2) 0.3726(3) 0.13041(7) 0.0249(5) Uani 1 1 d . . . . .
N4 N 0.3535(2) 0.4729(3) 0.14528(8) 0.0259(5) Uani 1 1 d . . . . .
O1 O 0.29353(18) 0.8249(3) 0.42674(7) 0.0363(5) Uani 1 1 d . . . . .
O2 O -0.4166(2) 0.1869(3) 0.35238(8) 0.0454(6) Uani 1 1 d . . . . .
O3 O 0.19714(17) 0.1877(2) 0.06924(7) 0.0308(5) Uani 1 1 d . . . . .
O4 O 0.9060(2) 0.8258(3) 0.14343(8) 0.0434(5) Uani 1 1 d . . . . .
S1 S 0.07291(7) 0.63251(13) 0.47952(2) 0.03837(19) Uani 1 1 d . . . . .
S2 S 0.51081(6) 0.13975(10) 0.08727(2) 0.02821(16) Uani 1 1 d . . . . .
C1 C 0.2215(2) 0.7248(4) 0.40669(9) 0.0271(6) Uani 1 1 d . . . . .
C2 C 0.0801(2) 0.6870(4) 0.41734(9) 0.0274(6) Uani 1 1 d . . . . .
C3 C 0.0480(3) 0.5508(4) 0.38272(9) 0.0264(6) Uani 1 1 d . . . . .
C4 C -0.0754(3) 0.4597(4) 0.37637(9) 0.0285(6) Uani 1 1 d . . . . .
C5 C -0.1773(3) 0.4786(4) 0.40651(10) 0.0357(7) Uani 1 1 d . . . . .
H5 H -0.1672 0.5533 0.4323 0.043 Uiso 1 1 calc R U . . .
C6 C -0.2927(3) 0.3909(4) 0.39966(10) 0.0356(7) Uani 1 1 d . . . . .
H6 H -0.3608 0.4057 0.4206 0.043 Uiso 1 1 calc R U . . .
C7 C -0.3086(3) 0.2813(4) 0.36226(10) 0.0332(7) Uani 1 1 d . . . . .
C8 C -0.2085(3) 0.2634(4) 0.33135(10) 0.0363(7) Uani 1 1 d . . . . .
H8 H -0.2191 0.1900 0.3053 0.044 Uiso 1 1 calc R U . . .
C9 C -0.0950(3) 0.3512(4) 0.33842(9) 0.0310(6) Uani 1 1 d . . . . .
H9 H -0.0279 0.3379 0.3170 0.037 Uiso 1 1 calc R U . . .
C10 C -0.5254(3) 0.2071(5) 0.38093(12) 0.0455(8) Uani 1 1 d . . . . .
H10A H -0.4995 0.1781 0.4138 0.068 Uiso 1 1 calc R U . . .
H10B H -0.5970 0.1355 0.3691 0.068 Uiso 1 1 calc R U . . .
H10C H -0.5545 0.3216 0.3795 0.068 Uiso 1 1 calc R U . . .
C11 C -0.0070(2) 0.8498(4) 0.40819(8) 0.0226(5) Uani 1 1 d . . . . .
H11A H -0.1004 0.8254 0.4120 0.027 Uiso 1 1 calc R U . . .
H11B H 0.0212 0.9367 0.4310 0.027 Uiso 1 1 calc R U . . .
C12 C 0.0130(3) 0.9062(4) 0.35717(10) 0.0328(7) Uani 1 1 d . . . . .
C13 C -0.0623(3) 0.8426(5) 0.31878(11) 0.0423(8) Uani 1 1 d . . . . .
H13 H -0.1279 0.7632 0.3238 0.051 Uiso 1 1 calc R U . . .
C14 C -0.0411(4) 0.8959(6) 0.27284(13) 0.0609(11) Uani 1 1 d . . . . .
H14 H -0.0927 0.8530 0.2467 0.073 Uiso 1 1 calc R U . . .
C15 C 0.0546(4) 1.0107(6) 0.26546(14) 0.0629(12) Uani 1 1 d . . . . .
H15 H 0.0693 1.0459 0.2342 0.076 Uiso 1 1 calc R U . . .
C16 C 0.1282(4) 1.0739(5) 0.30314(14) 0.0581(10) Uani 1 1 d . . . . .
H16 H 0.1936 1.1533 0.2980 0.070 Uiso 1 1 calc R U . . .
C17 C 0.1080(3) 1.0230(4) 0.34831(13) 0.0430(8) Uani 1 1 d . . . . .
H17 H 0.1597 1.0683 0.3741 0.052 Uiso 1 1 calc R U . . .
C18 C 0.3586(2) 0.6279(4) 0.34146(9) 0.0278(5) Uani 1 1 d . . . . .
C19 C 0.3592(3) 0.5316(4) 0.30130(10) 0.0338(7) Uani 1 1 d . . . . .
H19 H 0.2856 0.4653 0.2922 0.041 Uiso 1 1 calc R U . . .
C20 C 0.4681(3) 0.5321(5) 0.27426(11) 0.0416(8) Uani 1 1 d . . . . .
H20 H 0.4689 0.4648 0.2469 0.050 Uiso 1 1 calc R U . . .
C21 C 0.5742(3) 0.6287(6) 0.28675(10) 0.0441(8) Uani 1 1 d . . . . .
H21 H 0.6488 0.6271 0.2684 0.053 Uiso 1 1 calc R U . . .
C22 C 0.5723(3) 0.7286(5) 0.32623(12) 0.0481(9) Uani 1 1 d . . . . .
H22 H 0.6444 0.7985 0.3343 0.058 Uiso 1 1 calc R U . . .
C23 C 0.4653(3) 0.7271(5) 0.35421(11) 0.0416(8) Uani 1 1 d . . . . .
H23 H 0.4651 0.7934 0.3818 0.050 Uiso 1 1 calc R U . . .
C24 C 0.1943(3) 0.4796(4) 0.48687(10) 0.0305(6) Uani 1 1 d . . . . .
C25 C 0.1755(3) 0.3230(4) 0.46895(10) 0.0336(7) Uani 1 1 d . . . . .
H25 H 0.0992 0.2981 0.4495 0.040 Uiso 1 1 calc R U . . .
C26 C 0.2684(3) 0.2021(4) 0.47947(11) 0.0395(7) Uani 1 1 d . . . . .
H26 H 0.2557 0.0945 0.4672 0.047 Uiso 1 1 calc R U . . .
C27 C 0.3795(3) 0.2386(4) 0.50791(12) 0.0420(8) Uani 1 1 d . . . . .
H27 H 0.4423 0.1556 0.5156 0.050 Uiso 1 1 calc R U . . .
C28 C 0.3985(3) 0.3948(5) 0.52487(13) 0.0493(9) Uani 1 1 d . . . . .
H28 H 0.4754 0.4204 0.5438 0.059 Uiso 1 1 calc R U . . .
C29 C 0.3066(3) 0.5146(4) 0.51456(11) 0.0437(8) Uani 1 1 d . . . . .
H29 H 0.3205 0.6224 0.5266 0.052 Uiso 1 1 calc R U . . .
C30 C 0.2707(2) 0.2822(3) 0.09089(9) 0.0236(6) Uani 1 1 d . . . . .
C31 C 0.4092(2) 0.3265(3) 0.07907(9) 0.0230(5) Uani 1 1 d . . . . .
C32 C 0.4457(2) 0.4509(4) 0.11690(9) 0.0239(6) Uani 1 1 d . . . . .
C33 C 0.5699(2) 0.5409(3) 0.12319(9) 0.0247(6) Uani 1 1 d . . . . .
C34 C 0.6742(3) 0.5155(4) 0.09484(10) 0.0312(6) Uani 1 1 d . . . . .
H34 H 0.6672 0.4333 0.0710 0.037 Uiso 1 1 calc R U . . .
C35 C 0.7883(3) 0.6070(4) 0.10037(10) 0.0325(7) Uani 1 1 d . . . . .
H35 H 0.8583 0.5871 0.0806 0.039 Uiso 1 1 calc R U . . .
C36 C 0.7995(3) 0.7275(4) 0.13491(10) 0.0314(6) Uani 1 1 d . . . . .
C37 C 0.6972(3) 0.7534(4) 0.16379(10) 0.0339(7) Uani 1 1 d . . . . .
H37 H 0.7052 0.8352 0.1877 0.041 Uiso 1 1 calc R U . . .
C38 C 0.5842(2) 0.6627(4) 0.15839(9) 0.0294(6) Uani 1 1 d . . . . .
H38 H 0.5152 0.6823 0.1786 0.035 Uiso 1 1 calc R U . . .
C39 C 1.0148(3) 0.8019(5) 0.11520(12) 0.0429(8) Uani 1 1 d . . . . .
H39A H 1.0504 0.6916 0.1207 0.064 Uiso 1 1 calc R U . . .
H39B H 1.0823 0.8836 0.1238 0.064 Uiso 1 1 calc R U . . .
H39C H 0.9864 0.8142 0.0817 0.064 Uiso 1 1 calc R U . . .
C40 C 0.4109(2) 0.3831(4) 0.02701(9) 0.0267(6) Uani 1 1 d . . . . .
H40A H 0.5001 0.4200 0.0206 0.032 Uiso 1 1 calc R U . . .
H40B H 0.3882 0.2894 0.0058 0.032 Uiso 1 1 calc R U . . .
C41 C 0.3147(2) 0.5225(4) 0.01641(9) 0.0253(6) Uani 1 1 d . . . . .
C42 C 0.3405(3) 0.6821(4) 0.03147(9) 0.0290(6) Uani 1 1 d . . . . .
H42 H 0.4197 0.7058 0.0493 0.035 Uiso 1 1 calc R U . . .
C43 C 0.2520(3) 0.8070(4) 0.02077(10) 0.0354(7) Uani 1 1 d . . . . .
H43 H 0.2708 0.9156 0.0313 0.043 Uiso 1 1 calc R U . . .
C44 C 0.1367(3) 0.7742(4) -0.00514(11) 0.0375(7) Uani 1 1 d . . . . .
H44 H 0.0766 0.8603 -0.0127 0.045 Uiso 1 1 calc R U . . .
C45 C 0.1086(3) 0.6158(5) -0.02010(11) 0.0399(8) Uani 1 1 d . . . . .
H45 H 0.0288 0.5926 -0.0376 0.048 Uiso 1 1 calc R U . . .
C46 C 0.1975(3) 0.4909(4) -0.00938(11) 0.0341(7) Uani 1 1 d . . . . .
H46 H 0.1781 0.3824 -0.0198 0.041 Uiso 1 1 calc R U . . .
C47 C 0.1340(2) 0.3732(4) 0.15720(9) 0.0261(6) Uani 1 1 d . . . . .
C48 C 0.1324(3) 0.4723(4) 0.19726(10) 0.0329(7) Uani 1 1 d . . . . .
H48 H 0.2061 0.5373 0.2069 0.040 Uiso 1 1 calc R U . . .
C49 C 0.0210(3) 0.4742(4) 0.22285(11) 0.0413(8) Uani 1 1 d . . . . .
H49 H 0.0191 0.5411 0.2503 0.050 Uiso 1 1 calc R U . . .
C50 C -0.0867(3) 0.3811(5) 0.20924(11) 0.0431(8) Uani 1 1 d . . . . .
H50 H -0.1625 0.3845 0.2269 0.052 Uiso 1 1 calc R U . . .
C51 C -0.0837(3) 0.2831(5) 0.16977(11) 0.0433(8) Uani 1 1 d . . . . .
H51 H -0.1577 0.2181 0.1604 0.052 Uiso 1 1 calc R U . . .
C52 C 0.0261(3) 0.2778(4) 0.14344(11) 0.0359(7) Uani 1 1 d . . . . .
H52 H 0.0274 0.2096 0.1163 0.043 Uiso 1 1 calc R U . . .
C53 C 0.4695(3) 0.0832(4) 0.14533(10) 0.0291(6) Uani 1 1 d . . . . .
C54 C 0.5395(3) 0.1455(5) 0.18491(10) 0.0386(7) Uani 1 1 d . . . . .
H54 H 0.6088 0.2211 0.1814 0.046 Uiso 1 1 calc R U . . .
C55 C 0.5073(3) 0.0960(5) 0.22993(11) 0.0499(10) Uani 1 1 d . . . . .
H55 H 0.5553 0.1375 0.2571 0.060 Uiso 1 1 calc R U . . .
C56 C 0.4057(4) -0.0131(5) 0.23514(13) 0.0527(9) Uani 1 1 d . . . . .
H56 H 0.3845 -0.0469 0.2659 0.063 Uiso 1 1 calc R U . . .
C57 C 0.3356(3) -0.0725(5) 0.19602(12) 0.0470(8) Uani 1 1 d . . . . .
H57 H 0.2650 -0.1459 0.1997 0.056 Uiso 1 1 calc R U . . .
C58 C 0.3676(3) -0.0256(4) 0.15096(11) 0.0365(7) Uani 1 1 d . . . . .
H58 H 0.3196 -0.0682 0.1239 0.044 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
N1 C1 1.364(4) . ?
N1 N2 1.415(3) . ?
N1 C18 1.421(3) . ?
N2 C3 1.294(3) . ?
N3 C30 1.373(3) . ?
N3 N4 1.407(3) . ?
N3 C47 1.423(3) . ?
N4 C32 1.289(3) . ?
O1 C1 1.218(3) . ?
O2 C7 1.363(3) . ?
O2 C10 1.426(4) . ?
O3 C30 1.217(3) . ?
O4 C36 1.364(3) . ?
O4 C39 1.423(4) . ?
S1 C24 1.765(3) . ?
S1 C2 1.821(3) . ?
S2 C53 1.782(3) . ?
S2 C31 1.851(3) . ?
C1 C2 1.529(4) . ?
C2 C3 1.504(4) . ?
C2 C11 1.611(4) . ?
C3 C4 1.468(4) . ?
C4 C5 1.396(4) . ?
C4 C9 1.396(4) . ?
C5 C6 1.386(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(4) . ?
C8 C9 1.370(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.541(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.394(4) . ?
C12 C17 1.395(5) . ?
C13 C14 1.400(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.369(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.371(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.382(4) . ?
C18 C23 1.390(4) . ?
C19 C20 1.390(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.372(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.383(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.391(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C29 1.382(4) . ?
C24 C25 1.383(4) . ?
C25 C26 1.390(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.386(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.370(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.376(5) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 C31 1.521(3) . ?
C31 C32 1.506(4) . ?
C31 C40 1.545(3) . ?
C32 C33 1.470(4) . ?
C33 C34 1.390(4) . ?
C33 C38 1.408(4) . ?
C34 C35 1.387(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.386(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.384(4) . ?
C37 C38 1.375(4) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 C41 1.522(4) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C42 1.389(4) . ?
C41 C46 1.391(4) . ?
C42 C43 1.385(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.378(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.384(5) . ?
C44 H44 0.9500 . ?
C45 C46 1.387(4) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 C52 1.388(4) . ?
C47 C48 1.393(4) . ?
C48 C49 1.389(4) . ?
C48 H48 0.9500 . ?
C49 C50 1.374(5) . ?
C49 H49 0.9500 . ?
C50 C51 1.375(5) . ?
C50 H50 0.9500 . ?
C51 C52 1.387(4) . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
C53 C58 1.386(4) . ?
C53 C54 1.389(4) . ?
C54 C55 1.395(4) . ?
C54 H54 0.9500 . ?
C55 C56 1.384(5) . ?
C55 H55 0.9500 . ?
C56 C57 1.371(5) . ?
C56 H56 0.9500 . ?
C57 C58 1.390(4) . ?
C57 H57 0.9500 . ?
C58 H58 0.9500 . ?

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 N1 N2 112.6(2) . . ?
C1 N1 C18 129.0(2) . . ?
N2 N1 C18 118.2(2) . . ?
C3 N2 N1 108.1(2) . . ?
C30 N3 N4 112.6(2) . . ?
C30 N3 C47 128.7(2) . . ?
N4 N3 C47 118.7(2) . . ?
C32 N4 N3 108.5(2) . . ?
C7 O2 C10 118.2(3) . . ?
C36 O4 C39 117.8(3) . . ?
C24 S1 C2 102.51(13) . . ?
C53 S2 C31 99.48(12) . . ?
O1 C1 N1 127.6(2) . . ?
O1 C1 C2 126.7(3) . . ?
N1 C1 C2 105.6(2) . . ?
C3 C2 C1 101.1(2) . . ?
C3 C2 C11 114.0(2) . . ?
C1 C2 C11 109.0(2) . . ?
C3 C2 S1 115.4(2) . . ?
C1 C2 S1 109.52(18) . . ?
C11 C2 S1 107.55(17) . . ?
N2 C3 C4 120.3(3) . . ?
N2 C3 C2 112.4(2) . . ?
C4 C3 C2 127.3(2) . . ?
C5 C4 C9 117.5(3) . . ?
C5 C4 C3 122.6(3) . . ?
C9 C4 C3 119.8(2) . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 119.9(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
O2 C7 C6 125.2(3) . . ?
O2 C7 C8 115.5(3) . . ?
C6 C7 C8 119.3(3) . . ?
C9 C8 C7 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C4 121.6(3) . . ?
C8 C9 H9 119.2 . . ?
C4 C9 H9 119.2 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C2 107.0(2) . . ?
C12 C11 H11A 110.3 . . ?
C2 C11 H11A 110.3 . . ?
C12 C11 H11B 110.3 . . ?
C2 C11 H11B 110.3 . . ?
H11A C11 H11B 108.6 . . ?
C13 C12 C17 118.2(3) . . ?
C13 C12 C11 121.3(3) . . ?
C17 C12 C11 120.4(3) . . ?
C12 C13 C14 119.9(4) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 120.2(4) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.0(4) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.3(4) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 121.4(4) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
C19 C18 C23 120.1(2) . . ?
C19 C18 N1 119.8(3) . . ?
C23 C18 N1 120.1(3) . . ?
C18 C19 C20 119.6(3) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 120.7(3) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 119.7(3) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C23 120.3(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C18 C23 C22 119.5(3) . . ?
C18 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C29 C24 C25 119.4(3) . . ?
C29 C24 S1 118.5(3) . . ?
C25 C24 S1 121.8(2) . . ?
C24 C25 C26 119.8(3) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C27 C26 C25 120.0(3) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C28 C27 C26 119.8(3) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C27 C28 C29 120.3(3) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C28 C29 C24 120.6(3) . . ?
C28 C29 H29 119.7 . . ?
C24 C29 H29 119.7 . . ?
O3 C30 N3 128.0(2) . . ?
O3 C30 C31 126.7(2) . . ?
N3 C30 C31 105.4(2) . . ?
C32 C31 C30 101.4(2) . . ?
C32 C31 C40 117.4(2) . . ?
C30 C31 C40 110.2(2) . . ?
C32 C31 S2 110.58(17) . . ?
C30 C31 S2 107.63(19) . . ?
C40 C31 S2 109.04(18) . . ?
N4 C32 C33 121.2(2) . . ?
N4 C32 C31 112.1(2) . . ?
C33 C32 C31 126.7(2) . . ?
C34 C33 C38 117.5(2) . . ?
C34 C33 C32 123.1(2) . . ?
C38 C33 C32 119.3(2) . . ?
C35 C34 C33 121.8(3) . . ?
C35 C34 H34 119.1 . . ?
C33 C34 H34 119.1 . . ?
C36 C35 C34 119.6(3) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
O4 C36 C37 115.6(3) . . ?
O4 C36 C35 124.9(3) . . ?
C37 C36 C35 119.4(3) . . ?
C38 C37 C36 121.0(3) . . ?
C38 C37 H37 119.5 . . ?
C36 C37 H37 119.5 . . ?
C37 C38 C33 120.6(2) . . ?
C37 C38 H38 119.7 . . ?
C33 C38 H38 119.7 . . ?
O4 C39 H39A 109.5 . . ?
O4 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
O4 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C41 C40 C31 111.5(2) . . ?
C41 C40 H40A 109.3 . . ?
C31 C40 H40A 109.3 . . ?
C41 C40 H40B 109.3 . . ?
C31 C40 H40B 109.3 . . ?
H40A C40 H40B 108.0 . . ?
C42 C41 C46 118.4(3) . . ?
C42 C41 C40 122.0(2) . . ?
C46 C41 C40 119.6(3) . . ?
C43 C42 C41 120.8(3) . . ?
C43 C42 H42 119.6 . . ?
C41 C42 H42 119.6 . . ?
C44 C43 C42 120.1(3) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
C43 C44 C45 120.0(3) . . ?
C43 C44 H44 120.0 . . ?
C45 C44 H44 120.0 . . ?
C44 C45 C46 119.7(3) . . ?
C44 C45 H45 120.1 . . ?
C46 C45 H45 120.1 . . ?
C45 C46 C41 120.9(3) . . ?
C45 C46 H46 119.5 . . ?
C41 C46 H46 119.5 . . ?
C52 C47 C48 120.3(2) . . ?
C52 C47 N3 120.6(2) . . ?
C48 C47 N3 119.1(2) . . ?
C49 C48 C47 118.8(3) . . ?
C49 C48 H48 120.6 . . ?
C47 C48 H48 120.6 . . ?
C50 C49 C48 121.2(3) . . ?
C50 C49 H49 119.4 . . ?
C48 C49 H49 119.4 . . ?
C49 C50 C51 119.4(3) . . ?
C49 C50 H50 120.3 . . ?
C51 C50 H50 120.3 . . ?
C50 C51 C52 120.9(3) . . ?
C50 C51 H51 119.6 . . ?
C52 C51 H51 119.6 . . ?
C47 C52 C51 119.3(3) . . ?
C47 C52 H52 120.3 . . ?
C51 C52 H52 120.3 . . ?
C58 C53 C54 119.8(3) . . ?
C58 C53 S2 119.6(2) . . ?
C54 C53 S2 120.6(2) . . ?
C53 C54 C55 119.4(3) . . ?
C53 C54 H54 120.3 . . ?
C55 C54 H54 120.3 . . ?
C56 C55 C54 120.3(3) . . ?
C56 C55 H55 119.9 . . ?
C54 C55 H55 119.9 . . ?
C57 C56 C55 120.1(3) . . ?
C57 C56 H56 120.0 . . ?
C55 C56 H56 119.9 . . ?
C56 C57 C58 120.2(3) . . ?
C56 C57 H57 119.9 . . ?
C58 C57 H57 119.9 . . ?
C53 C58 C57 120.2(3) . . ?
C53 C58 H58 119.9 . . ?
C57 C58 H58 119.9 . . ?

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
C1 N1 N2 C3 1.9(3) . . . . ?
C18 N1 N2 C3 -173.6(3) . . . . ?
C30 N3 N4 C32 -0.1(3) . . . . ?
C47 N3 N4 C32 178.6(2) . . . . ?
N2 N1 C1 O1 178.0(3) . . . . ?
C18 N1 C1 O1 -7.1(5) . . . . ?
N2 N1 C1 C2 -3.9(3) . . . . ?
C18 N1 C1 C2 171.0(3) . . . . ?
O1 C1 C2 C3 -177.8(3) . . . . ?
N1 C1 C2 C3 4.1(3) . . . . ?
O1 C1 C2 C11 61.9(3) . . . . ?
N1 C1 C2 C11 -116.3(2) . . . . ?
O1 C1 C2 S1 -55.5(4) . . . . ?
N1 C1 C2 S1 126.3(2) . . . . ?
C24 S1 C2 C3 62.1(2) . . . . ?
C24 S1 C2 C1 -51.2(2) . . . . ?
C24 S1 C2 C11 -169.48(18) . . . . ?
N1 N2 C3 C4 179.2(2) . . . . ?
N1 N2 C3 C2 1.1(3) . . . . ?
C1 C2 C3 N2 -3.2(3) . . . . ?
C11 C2 C3 N2 113.5(3) . . . . ?
S1 C2 C3 N2 -121.3(2) . . . . ?
C1 C2 C3 C4 178.8(3) . . . . ?
C11 C2 C3 C4 -64.4(4) . . . . ?
S1 C2 C3 C4 60.8(3) . . . . ?
N2 C3 C4 C5 175.1(3) . . . . ?
C2 C3 C4 C5 -7.1(5) . . . . ?
N2 C3 C4 C9 -6.1(4) . . . . ?
C2 C3 C4 C9 171.7(3) . . . . ?
C9 C4 C5 C6 1.2(5) . . . . ?
C3 C4 C5 C6 -180.0(3) . . . . ?
C4 C5 C6 C7 0.1(5) . . . . ?
C10 O2 C7 C6 3.5(4) . . . . ?
C10 O2 C7 C8 -176.2(3) . . . . ?
C5 C6 C7 O2 179.1(3) . . . . ?
C5 C6 C7 C8 -1.3(5) . . . . ?
O2 C7 C8 C9 -179.2(3) . . . . ?
C6 C7 C8 C9 1.1(5) . . . . ?
C7 C8 C9 C4 0.3(5) . . . . ?
C5 C4 C9 C8 -1.4(4) . . . . ?
C3 C4 C9 C8 179.8(3) . . . . ?
C3 C2 C11 C12 -57.3(3) . . . . ?
C1 C2 C11 C12 54.8(3) . . . . ?
S1 C2 C11 C12 173.42(18) . . . . ?
C2 C11 C12 C13 85.9(3) . . . . ?
C2 C11 C12 C17 -94.0(3) . . . . ?
C17 C12 C13 C14 0.2(5) . . . . ?
C11 C12 C13 C14 -179.7(3) . . . . ?
C12 C13 C14 C15 0.3(5) . . . . ?
C13 C14 C15 C16 -0.6(6) . . . . ?
C14 C15 C16 C17 0.4(6) . . . . ?
C15 C16 C17 C12 0.2(5) . . . . ?
C13 C12 C17 C16 -0.5(5) . . . . ?
C11 C12 C17 C16 179.4(3) . . . . ?
C1 N1 C18 C19 -172.0(3) . . . . ?
N2 N1 C18 C19 2.7(4) . . . . ?
C1 N1 C18 C23 7.2(5) . . . . ?
N2 N1 C18 C23 -178.2(3) . . . . ?
C23 C18 C19 C20 1.2(5) . . . . ?
N1 C18 C19 C20 -179.6(3) . . . . ?
C18 C19 C20 C21 -0.8(5) . . . . ?
C19 C20 C21 C22 -1.0(6) . . . . ?
C20 C21 C22 C23 2.2(6) . . . . ?
C19 C18 C23 C22 0.0(5) . . . . ?
N1 C18 C23 C22 -179.1(3) . . . . ?
C21 C22 C23 C18 -1.8(6) . . . . ?
C2 S1 C24 C29 111.4(3) . . . . ?
C2 S1 C24 C25 -73.9(3) . . . . ?
C29 C24 C25 C26 0.9(4) . . . . ?
S1 C24 C25 C26 -173.8(2) . . . . ?
C24 C25 C26 C27 0.1(4) . . . . ?
C25 C26 C27 C28 -1.2(5) . . . . ?
C26 C27 C28 C29 1.3(5) . . . . ?
C27 C28 C29 C24 -0.2(5) . . . . ?
C25 C24 C29 C28 -0.9(5) . . . . ?
S1 C24 C29 C28 174.0(3) . . . . ?
N4 N3 C30 O3 -178.3(3) . . . . ?
C47 N3 C30 O3 3.2(5) . . . . ?
N4 N3 C30 C31 1.0(3) . . . . ?
C47 N3 C30 C31 -177.5(2) . . . . ?
O3 C30 C31 C32 177.9(3) . . . . ?
N3 C30 C31 C32 -1.4(3) . . . . ?
O3 C30 C31 C40 52.9(4) . . . . ?
N3 C30 C31 C40 -126.5(2) . . . . ?
O3 C30 C31 S2 -65.9(3) . . . . ?
N3 C30 C31 S2 114.7(2) . . . . ?
C53 S2 C31 C32 58.9(2) . . . . ?
C53 S2 C31 C30 -51.02(19) . . . . ?
C53 S2 C31 C40 -170.57(18) . . . . ?
N3 N4 C32 C33 179.4(2) . . . . ?
N3 N4 C32 C31 -0.9(3) . . . . ?
C30 C31 C32 N4 1.5(3) . . . . ?
C40 C31 C32 N4 121.6(3) . . . . ?
S2 C31 C32 N4 -112.5(2) . . . . ?
C30 C31 C32 C33 -178.9(3) . . . . ?
C40 C31 C32 C33 -58.8(3) . . . . ?
S2 C31 C32 C33 67.1(3) . . . . ?
N4 C32 C33 C34 176.9(3) . . . . ?
C31 C32 C33 C34 -2.7(4) . . . . ?
N4 C32 C33 C38 -5.3(4) . . . . ?
C31 C32 C33 C38 175.1(2) . . . . ?
C38 C33 C34 C35 -0.6(4) . . . . ?
C32 C33 C34 C35 177.3(3) . . . . ?
C33 C34 C35 C36 -0.2(4) . . . . ?
C39 O4 C36 C37 178.9(3) . . . . ?
C39 O4 C36 C35 -0.7(4) . . . . ?
C34 C35 C36 O4 -179.5(3) . . . . ?
C34 C35 C36 C37 0.8(4) . . . . ?
O4 C36 C37 C38 179.6(3) . . . . ?
C35 C36 C37 C38 -0.7(5) . . . . ?
C36 C37 C38 C33 0.0(5) . . . . ?
C34 C33 C38 C37 0.7(4) . . . . ?
C32 C33 C38 C37 -177.3(3) . . . . ?
C32 C31 C40 C41 -60.9(3) . . . . ?
C30 C31 C40 C41 54.4(3) . . . . ?
S2 C31 C40 C41 172.37(18) . . . . ?
C31 C40 C41 C42 75.8(3) . . . . ?
C31 C40 C41 C46 -104.7(3) . . . . ?
C46 C41 C42 C43 -0.5(4) . . . . ?
C40 C41 C42 C43 179.1(2) . . . . ?
C41 C42 C43 C44 0.0(4) . . . . ?
C42 C43 C44 C45 0.6(5) . . . . ?
C43 C44 C45 C46 -0.7(5) . . . . ?
C44 C45 C46 C41 0.2(5) . . . . ?
C42 C41 C46 C45 0.4(4) . . . . ?
C40 C41 C46 C45 -179.2(3) . . . . ?
C30 N3 C47 C52 -2.5(4) . . . . ?
N4 N3 C47 C52 179.1(3) . . . . ?
C30 N3 C47 C48 178.2(3) . . . . ?
N4 N3 C47 C48 -0.2(4) . . . . ?
C52 C47 C48 C49 -0.3(4) . . . . ?
N3 C47 C48 C49 179.0(3) . . . . ?
C47 C48 C49 C50 -0.2(5) . . . . ?
C48 C49 C50 C51 0.6(5) . . . . ?
C49 C50 C51 C52 -0.4(5) . . . . ?
C48 C47 C52 C51 0.5(5) . . . . ?
N3 C47 C52 C51 -178.9(3) . . . . ?
C50 C51 C52 C47 -0.1(5) . . . . ?
C31 S2 C53 C58 92.5(2) . . . . ?
C31 S2 C53 C54 -88.4(3) . . . . ?
C58 C53 C54 C55 0.7(5) . . . . ?
S2 C53 C54 C55 -178.4(2) . . . . ?
C53 C54 C55 C56 -0.5(5) . . . . ?
C54 C55 C56 C57 -0.4(5) . . . . ?
C55 C56 C57 C58 1.1(6) . . . . ?
C54 C53 C58 C57 0.0(5) . . . . ?
S2 C53 C58 C57 179.1(2) . . . . ?
C56 C57 C58 C53 -0.9(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C52 H52 O3 0.95 2.26 2.910(3) 124.9 .
C23 H23 O1 0.95 2.25 2.896(4) 124.8 .

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-4

