# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

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

data_cd17102
_database_code_depnum_ccdc_archive 'CCDC 1535807'
_audit_update_record             
;
2017-03-03 deposited with the CCDC.
2018-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 Br N O2 S'
_chemical_formula_weight         454.37

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'
Br Br -0.2901 2.4595 '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                   10.0726(19)
_cell_length_b                   10.735(2)
_cell_length_c                   19.604(4)
_cell_angle_alpha                82.045(4)
_cell_angle_beta                 86.428(5)
_cell_angle_gamma                81.212(5)
_cell_volume                     2073.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1106
_cell_measurement_theta_min      4.523
_cell_measurement_theta_max      37.303

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    2.102
_shelx_estimated_absorpt_T_min   0.743
_shelx_estimated_absorpt_T_max   0.833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6218
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11488
_diffrn_reflns_av_unetI/netI     0.1029
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.050
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             7263
_reflns_number_gt                3721
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0592P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7263
_refine_ls_number_parameters     515
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1556
_refine_ls_wR_factor_gt          0.1248
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_refine_ls_shift/su_max          0.013
_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
Br1 Br 0.53952(7) 1.14516(7) 0.33445(4) 0.0936(3) Uani 1 1 d . . . . .
Br2 Br 0.98324(8) 0.58013(10) 1.15638(5) 0.1221(4) Uani 1 1 d . . . . .
S1 S 0.95331(13) 0.04744(14) 0.88545(7) 0.0533(4) Uani 1 1 d . . . . .
S2 S 0.42893(12) 0.50238(13) 0.61269(7) 0.0476(4) Uani 1 1 d . . . . .
N1 N 0.8498(4) 0.1348(5) 0.9319(2) 0.0558(13) Uani 1 1 d . . . . .
N2 N 0.3393(4) 0.6112(4) 0.5619(2) 0.0515(12) Uani 1 1 d . . . . .
O1 O 0.9808(3) 0.1197(4) 0.82109(17) 0.0602(10) Uani 1 1 d . . . . .
O2 O 1.0619(3) -0.0041(4) 0.92924(18) 0.0680(11) Uani 1 1 d . . . . .
O3 O 0.5499(3) 0.4700(3) 0.57316(17) 0.0563(10) Uani 1 1 d . . . . .
O4 O 0.4364(3) 0.5469(3) 0.67718(16) 0.0555(9) Uani 1 1 d . . . . .
C1 C 0.7235(5) 0.2053(5) 0.9123(2) 0.0460(13) Uani 1 1 d . . . . .
C2 C 0.6899(6) 0.2372(6) 0.8437(3) 0.0604(15) Uani 1 1 d . . . . .
H2 H 0.7504 0.2102 0.8091 0.072 Uiso 1 1 calc R U . . .
C3 C 0.5695(6) 0.3072(6) 0.8265(3) 0.0658(16) Uani 1 1 d . . . . .
H3 H 0.5476 0.3261 0.7805 0.079 Uiso 1 1 calc R U . . .
C4 C 0.4811(6) 0.3499(6) 0.8764(3) 0.0760(18) Uani 1 1 d . . . . .
H4 H 0.3990 0.3982 0.8649 0.091 Uiso 1 1 calc R U . . .
C5 C 0.5150(5) 0.3203(6) 0.9443(3) 0.0609(15) Uani 1 1 d . . . . .
H5 H 0.4547 0.3507 0.9781 0.073 Uiso 1 1 calc R U . . .
C6 C 0.6343(5) 0.2478(5) 0.9643(2) 0.0435(12) Uani 1 1 d . . . . .
C7 C 0.6671(4) 0.2187(5) 1.0383(2) 0.0457(13) Uani 1 1 d . . . . .
C8 C 0.6263(5) 0.1189(6) 1.0763(3) 0.0556(14) Uani 1 1 d . . . . .
C9 C 0.5610(7) 0.0053(6) 1.0796(3) 0.085(2) Uani 1 1 d . . . . .
H9A H 0.6078 -0.0657 1.0578 0.103 Uiso 1 1 calc R U . . .
H9B H 0.4638 0.0168 1.0780 0.103 Uiso 1 1 calc R U . . .
C10 C 0.6212(6) 0.0387(6) 1.1419(3) 0.0796(19) Uani 1 1 d . . . . .
H10A H 0.5601 0.0700 1.1780 0.096 Uiso 1 1 calc R U . . .
H10B H 0.7040 -0.0124 1.1578 0.096 Uiso 1 1 calc R U . . .
C11 C 0.7434(5) 0.3048(5) 1.0669(2) 0.0489(13) Uani 1 1 d . . . . .
C12 C 0.7772(6) 0.2871(7) 1.1355(3) 0.0793(19) Uani 1 1 d . . . . .
H12 H 0.7509 0.2182 1.1645 0.095 Uiso 1 1 calc R U . . .
C13 C 0.8480(7) 0.3671(8) 1.1620(3) 0.091(2) Uani 1 1 d . . . . .
H13 H 0.8687 0.3528 1.2083 0.109 Uiso 1 1 calc R U . . .
C14 C 0.8878(6) 0.4676(7) 1.1202(4) 0.0710(18) Uani 1 1 d . . . . .
C15 C 0.8570(6) 0.4884(6) 1.0533(3) 0.0769(18) Uani 1 1 d . . . . .
H15 H 0.8829 0.5583 1.0250 0.092 Uiso 1 1 calc R U . . .
C16 C 0.7871(5) 0.4062(6) 1.0267(3) 0.0617(15) Uani 1 1 d . . . . .
H16 H 0.7693 0.4204 0.9801 0.074 Uiso 1 1 calc R U . . .
C17 C 0.8677(5) -0.0747(5) 0.8676(3) 0.0530(14) Uani 1 1 d . . . . .
C18 C 0.8320(5) -0.0813(6) 0.8030(3) 0.0598(15) Uani 1 1 d . . . . .
H18 H 0.8541 -0.0214 0.7668 0.072 Uiso 1 1 calc R U . . .
C19 C 0.7626(6) -0.1772(6) 0.7908(3) 0.0723(17) Uani 1 1 d . . . . .
H19 H 0.7395 -0.1815 0.7461 0.087 Uiso 1 1 calc R U . . .
C20 C 0.7270(6) -0.2661(6) 0.8434(4) 0.0762(18) Uani 1 1 d . . . . .
C21 C 0.7664(7) -0.2576(7) 0.9084(4) 0.092(2) Uani 1 1 d . . . . .
H21 H 0.7453 -0.3177 0.9447 0.111 Uiso 1 1 calc R U . . .
C22 C 0.8361(6) -0.1631(6) 0.9213(3) 0.0797(19) Uani 1 1 d . . . . .
H22 H 0.8613 -0.1592 0.9658 0.096 Uiso 1 1 calc R U . . .
C23 C 0.6502(7) -0.3687(6) 0.8314(4) 0.113(3) Uani 1 1 d . . . . .
H23A H 0.5802 -0.3341 0.8001 0.170 Uiso 1 1 calc R U . . .
H23B H 0.6111 -0.4036 0.8744 0.170 Uiso 1 1 calc R U . . .
H23C H 0.7098 -0.4345 0.8119 0.170 Uiso 1 1 calc R U . . .
C24 C 0.2069(5) 0.6723(5) 0.5764(2) 0.0448(12) Uani 1 1 d . . . . .
C25 C 0.1533(5) 0.6702(5) 0.6435(3) 0.0630(16) Uani 1 1 d . . . . .
H25 H 0.2033 0.6273 0.6802 0.076 Uiso 1 1 calc R U . . .
C26 C 0.0264(6) 0.7318(6) 0.6550(3) 0.0707(18) Uani 1 1 d . . . . .
H26 H -0.0111 0.7277 0.6997 0.085 Uiso 1 1 calc R U . . .
C27 C -0.0457(6) 0.7989(6) 0.6021(3) 0.0752(18) Uani 1 1 d . . . . .
H27 H -0.1311 0.8420 0.6107 0.090 Uiso 1 1 calc R U . . .
C28 C 0.0077(5) 0.8027(6) 0.5366(3) 0.0671(17) Uani 1 1 d . . . . .
H28 H -0.0420 0.8500 0.5009 0.081 Uiso 1 1 calc R U . . .
C29 C 0.1338(5) 0.7383(5) 0.5211(2) 0.0470(13) Uani 1 1 d . . . . .
C30 C 0.1860(4) 0.7383(5) 0.4486(2) 0.0437(12) Uani 1 1 d . . . . .
C31 C 0.1490(5) 0.6570(5) 0.4116(3) 0.0495(13) Uani 1 1 d . . . . .
C32 C 0.1537(6) 0.6037(6) 0.3476(3) 0.0714(17) Uani 1 1 d . . . . .
H32A H 0.2372 0.5538 0.3338 0.086 Uiso 1 1 calc R U . . .
H32B H 0.1028 0.6526 0.3099 0.086 Uiso 1 1 calc R U . . .
C33 C 0.0765(6) 0.5509(6) 0.4106(3) 0.0774(18) Uani 1 1 d . . . . .
H33A H -0.0209 0.5680 0.4109 0.093 Uiso 1 1 calc R U . . .
H33B H 0.1134 0.4691 0.4348 0.093 Uiso 1 1 calc R U . . .
C34 C 0.2745(5) 0.8338(5) 0.4211(2) 0.0439(12) Uani 1 1 d . . . . .
C35 C 0.3065(5) 0.9204(5) 0.4608(3) 0.0498(13) Uani 1 1 d . . . . .
H35 H 0.2738 0.9175 0.5063 0.060 Uiso 1 1 calc R U . . .
C36 C 0.3858(5) 1.0112(5) 0.4349(3) 0.0552(14) Uani 1 1 d . . . . .
H36 H 0.4054 1.0690 0.4626 0.066 Uiso 1 1 calc R U . . .
C37 C 0.4351(5) 1.0161(5) 0.3689(3) 0.0570(14) Uani 1 1 d . . . . .
C38 C 0.4088(6) 0.9299(6) 0.3278(3) 0.0651(16) Uani 1 1 d . . . . .
H38 H 0.4442 0.9325 0.2827 0.078 Uiso 1 1 calc R U . . .
C39 C 0.3298(5) 0.8402(5) 0.3541(3) 0.0574(15) Uani 1 1 d . . . . .
H39 H 0.3125 0.7815 0.3262 0.069 Uiso 1 1 calc R U . . .
C40 C 0.3424(4) 0.3701(5) 0.6278(2) 0.0452(13) Uani 1 1 d . . . . .
C41 C 0.3336(5) 0.3008(6) 0.5742(3) 0.0597(15) Uani 1 1 d . . . . .
H41 H 0.3747 0.3222 0.5312 0.072 Uiso 1 1 calc R U . . .
C42 C 0.2630(5) 0.1998(6) 0.5858(3) 0.0634(16) Uani 1 1 d . . . . .
H42 H 0.2569 0.1529 0.5499 0.076 Uiso 1 1 calc R U . . .
C43 C 0.2001(5) 0.1652(6) 0.6492(3) 0.0592(15) Uani 1 1 d . . . . .
C44 C 0.2110(5) 0.2372(6) 0.7011(3) 0.0630(16) Uani 1 1 d . . . . .
H44 H 0.1699 0.2164 0.7441 0.076 Uiso 1 1 calc R U . . .
C45 C 0.2815(5) 0.3392(5) 0.6906(3) 0.0551(14) Uani 1 1 d . . . . .
H45 H 0.2874 0.3866 0.7263 0.066 Uiso 1 1 calc R U . . .
C46 C 0.1194(6) 0.0578(6) 0.6604(3) 0.085(2) Uani 1 1 d . . . . .
H46A H 0.1492 0.0008 0.7004 0.127 Uiso 1 1 calc R U . . .
H46B H 0.1312 0.0129 0.6208 0.127 Uiso 1 1 calc R U . . .
H46C H 0.0261 0.0906 0.6670 0.127 Uiso 1 1 calc R U . . .
H1 H 0.860(5) 0.113(5) 0.972(2) 0.051(17) Uiso 1 1 d . . . . .
H2A H 0.353(4) 0.596(4) 0.520(2) 0.040(14) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C37 1.892(5) . ?
Br2 C14 1.888(6) . ?
S1 O1 1.422(3) . ?
S1 O2 1.429(4) . ?
S1 N1 1.618(5) . ?
S1 C17 1.759(5) . ?
S2 O4 1.422(3) . ?
S2 O3 1.426(3) . ?
S2 N2 1.625(4) . ?
S2 C40 1.758(5) . ?
N1 C1 1.423(6) . ?
N1 H1 0.79(5) . ?
N2 C24 1.423(6) . ?
N2 H2A 0.86(4) . ?
C1 C2 1.391(7) . ?
C1 C6 1.393(6) . ?
C2 C3 1.360(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.360(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.489(6) . ?
C7 C8 1.322(7) . ?
C7 C11 1.474(7) . ?
C8 C10 1.448(8) . ?
C8 C9 1.463(8) . ?
C9 C10 1.506(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.366(7) . ?
C11 C12 1.388(7) . ?
C12 C13 1.369(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.356(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.347(8) . ?
C15 C16 1.383(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.352(7) . ?
C17 C22 1.374(7) . ?
C18 C19 1.384(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.375(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.376(9) . ?
C20 C23 1.491(8) . ?
C21 C22 1.378(9) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.388(6) . ?
C24 C29 1.396(7) . ?
C25 C26 1.367(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.360(8) . ?
C26 H26 0.9300 . ?
C27 C28 1.360(7) . ?
C27 H27 0.9300 . ?
C28 C29 1.387(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.486(6) . ?
C30 C31 1.317(6) . ?
C30 C34 1.484(7) . ?
C31 C32 1.445(7) . ?
C31 C33 1.447(7) . ?
C32 C33 1.509(8) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.378(6) . ?
C34 C39 1.392(6) . ?
C35 C36 1.377(7) . ?
C35 H35 0.9300 . ?
C36 C37 1.353(7) . ?
C36 H36 0.9300 . ?
C37 C38 1.373(7) . ?
C38 C39 1.369(7) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C40 C45 1.363(6) . ?
C40 C41 1.384(7) . ?
C41 C42 1.371(7) . ?
C41 H41 0.9300 . ?
C42 C43 1.389(7) . ?
C42 H42 0.9300 . ?
C43 C44 1.380(7) . ?
C43 C46 1.494(7) . ?
C44 C45 1.380(7) . ?
C44 H44 0.9300 . ?
C45 H45 0.9300 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 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
O1 S1 O2 119.0(2) . . ?
O1 S1 N1 109.4(2) . . ?
O2 S1 N1 104.7(2) . . ?
O1 S1 C17 106.7(2) . . ?
O2 S1 C17 110.1(3) . . ?
N1 S1 C17 106.4(2) . . ?
O4 S2 O3 119.2(2) . . ?
O4 S2 N2 109.2(2) . . ?
O3 S2 N2 104.5(2) . . ?
O4 S2 C40 107.3(2) . . ?
O3 S2 C40 108.9(2) . . ?
N2 S2 C40 107.2(2) . . ?
C1 N1 S1 126.9(4) . . ?
C1 N1 H1 117(4) . . ?
S1 N1 H1 111(4) . . ?
C24 N2 S2 126.6(3) . . ?
C24 N2 H2A 114(3) . . ?
S2 N2 H2A 110(3) . . ?
C2 C1 C6 119.8(5) . . ?
C2 C1 N1 122.3(5) . . ?
C6 C1 N1 117.9(4) . . ?
C3 C2 C1 120.9(5) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 120.3(5) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.0(6) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 122.8(5) . . ?
C6 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C5 C6 C1 117.2(5) . . ?
C5 C6 C7 121.0(4) . . ?
C1 C6 C7 121.8(4) . . ?
C8 C7 C11 122.3(5) . . ?
C8 C7 C6 119.7(5) . . ?
C11 C7 C6 118.0(4) . . ?
C7 C8 C10 149.5(6) . . ?
C7 C8 C9 148.1(5) . . ?
C10 C8 C9 62.3(4) . . ?
C8 C9 C10 58.3(4) . . ?
C8 C9 H9A 117.9 . . ?
C10 C9 H9A 117.9 . . ?
C8 C9 H9B 117.9 . . ?
C10 C9 H9B 117.9 . . ?
H9A C9 H9B 115.1 . . ?
C8 C10 C9 59.3(4) . . ?
C8 C10 H10A 117.8 . . ?
C9 C10 H10A 117.8 . . ?
C8 C10 H10B 117.8 . . ?
C9 C10 H10B 117.8 . . ?
H10A C10 H10B 115.0 . . ?
C16 C11 C12 116.0(5) . . ?
C16 C11 C7 121.6(5) . . ?
C12 C11 C7 122.5(5) . . ?
C13 C12 C11 122.4(6) . . ?
C13 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C14 C13 C12 119.5(6) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C15 C14 C13 120.1(6) . . ?
C15 C14 Br2 120.0(6) . . ?
C13 C14 Br2 119.9(5) . . ?
C14 C15 C16 120.1(6) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 121.9(6) . . ?
C11 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C18 C17 C22 120.4(5) . . ?
C18 C17 S1 121.4(4) . . ?
C22 C17 S1 118.2(5) . . ?
C17 C18 C19 120.0(6) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 121.3(6) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 117.1(6) . . ?
C19 C20 C23 122.0(7) . . ?
C21 C20 C23 120.8(7) . . ?
C20 C21 C22 122.2(6) . . ?
C20 C21 H21 118.9 . . ?
C22 C21 H21 118.9 . . ?
C17 C22 C21 118.9(6) . . ?
C17 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C29 120.8(5) . . ?
C25 C24 N2 121.4(5) . . ?
C29 C24 N2 117.8(4) . . ?
C26 C25 C24 119.3(5) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C27 C26 C25 121.0(5) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C28 C27 C26 119.7(6) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C27 C28 C29 122.1(5) . . ?
C27 C28 H28 118.9 . . ?
C29 C28 H28 118.9 . . ?
C28 C29 C24 117.0(5) . . ?
C28 C29 C30 120.8(5) . . ?
C24 C29 C30 122.2(4) . . ?
C31 C30 C34 123.5(4) . . ?
C31 C30 C29 119.0(4) . . ?
C34 C30 C29 117.5(4) . . ?
C30 C31 C32 150.3(5) . . ?
C30 C31 C33 146.7(5) . . ?
C32 C31 C33 62.9(4) . . ?
C31 C32 C33 58.6(3) . . ?
C31 C32 H32A 117.9 . . ?
C33 C32 H32A 117.9 . . ?
C31 C32 H32B 117.9 . . ?
C33 C32 H32B 117.9 . . ?
H32A C32 H32B 115.1 . . ?
C31 C33 C32 58.5(3) . . ?
C31 C33 H33A 117.9 . . ?
C32 C33 H33A 117.9 . . ?
C31 C33 H33B 117.9 . . ?
C32 C33 H33B 117.9 . . ?
H33A C33 H33B 115.1 . . ?
C35 C34 C39 116.5(5) . . ?
C35 C34 C30 121.7(4) . . ?
C39 C34 C30 121.8(4) . . ?
C36 C35 C34 121.7(5) . . ?
C36 C35 H35 119.1 . . ?
C34 C35 H35 119.1 . . ?
C37 C36 C35 119.9(5) . . ?
C37 C36 H36 120.1 . . ?
C35 C36 H36 120.1 . . ?
C36 C37 C38 120.6(5) . . ?
C36 C37 Br1 118.6(4) . . ?
C38 C37 Br1 120.8(4) . . ?
C39 C38 C37 119.0(5) . . ?
C39 C38 H38 120.5 . . ?
C37 C38 H38 120.5 . . ?
C38 C39 C34 122.2(5) . . ?
C38 C39 H39 118.9 . . ?
C34 C39 H39 118.9 . . ?
C45 C40 C41 120.7(5) . . ?
C45 C40 S2 120.5(4) . . ?
C41 C40 S2 118.8(4) . . ?
C42 C41 C40 118.5(5) . . ?
C42 C41 H41 120.7 . . ?
C40 C41 H41 120.7 . . ?
C41 C42 C43 122.3(5) . . ?
C41 C42 H42 118.8 . . ?
C43 C42 H42 118.8 . . ?
C44 C43 C42 117.2(5) . . ?
C44 C43 C46 121.0(5) . . ?
C42 C43 C46 121.8(5) . . ?
C45 C44 C43 121.5(5) . . ?
C45 C44 H44 119.3 . . ?
C43 C44 H44 119.3 . . ?
C40 C45 C44 119.7(5) . . ?
C40 C45 H45 120.1 . . ?
C44 C45 H45 120.1 . . ?
C43 C46 H46A 109.5 . . ?
C43 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C43 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 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
O1 S1 N1 C1 52.8(5) . . . . ?
O2 S1 N1 C1 -178.7(4) . . . . ?
C17 S1 N1 C1 -62.1(5) . . . . ?
O4 S2 N2 C24 -53.6(5) . . . . ?
O3 S2 N2 C24 177.9(4) . . . . ?
C40 S2 N2 C24 62.4(5) . . . . ?
S1 N1 C1 C2 -19.0(8) . . . . ?
S1 N1 C1 C6 163.9(4) . . . . ?
C6 C1 C2 C3 -1.4(8) . . . . ?
N1 C1 C2 C3 -178.4(5) . . . . ?
C1 C2 C3 C4 1.5(9) . . . . ?
C2 C3 C4 C5 -0.4(9) . . . . ?
C3 C4 C5 C6 -0.9(9) . . . . ?
C4 C5 C6 C1 1.0(8) . . . . ?
C4 C5 C6 C7 179.7(5) . . . . ?
C2 C1 C6 C5 0.1(7) . . . . ?
N1 C1 C6 C5 177.3(5) . . . . ?
C2 C1 C6 C7 -178.6(5) . . . . ?
N1 C1 C6 C7 -1.4(7) . . . . ?
C5 C6 C7 C8 86.9(6) . . . . ?
C1 C6 C7 C8 -94.4(6) . . . . ?
C5 C6 C7 C11 -92.3(6) . . . . ?
C1 C6 C7 C11 86.4(6) . . . . ?
C11 C7 C8 C10 -2.4(13) . . . . ?
C6 C7 C8 C10 178.4(9) . . . . ?
C11 C7 C8 C9 -175.5(8) . . . . ?
C6 C7 C8 C9 5.3(12) . . . . ?
C7 C8 C9 C10 176.0(10) . . . . ?
C7 C8 C10 C9 -175.9(11) . . . . ?
C8 C7 C11 C16 178.7(5) . . . . ?
C6 C7 C11 C16 -2.0(7) . . . . ?
C8 C7 C11 C12 -0.2(8) . . . . ?
C6 C7 C11 C12 179.1(5) . . . . ?
C16 C11 C12 C13 1.1(9) . . . . ?
C7 C11 C12 C13 -179.9(6) . . . . ?
C11 C12 C13 C14 -0.3(10) . . . . ?
C12 C13 C14 C15 0.3(10) . . . . ?
C12 C13 C14 Br2 179.1(5) . . . . ?
C13 C14 C15 C16 -1.2(10) . . . . ?
Br2 C14 C15 C16 -180.0(4) . . . . ?
C12 C11 C16 C15 -2.0(8) . . . . ?
C7 C11 C16 C15 179.0(5) . . . . ?
C14 C15 C16 C11 2.1(9) . . . . ?
O1 S1 C17 C18 -4.5(5) . . . . ?
O2 S1 C17 C18 -135.0(4) . . . . ?
N1 S1 C17 C18 112.2(5) . . . . ?
O1 S1 C17 C22 176.3(4) . . . . ?
O2 S1 C17 C22 45.9(5) . . . . ?
N1 S1 C17 C22 -67.0(5) . . . . ?
C22 C17 C18 C19 0.3(8) . . . . ?
S1 C17 C18 C19 -178.8(4) . . . . ?
C17 C18 C19 C20 0.8(9) . . . . ?
C18 C19 C20 C21 -1.6(9) . . . . ?
C18 C19 C20 C23 178.9(6) . . . . ?
C19 C20 C21 C22 1.3(10) . . . . ?
C23 C20 C21 C22 -179.2(6) . . . . ?
C18 C17 C22 C21 -0.6(9) . . . . ?
S1 C17 C22 C21 178.6(5) . . . . ?
C20 C21 C22 C17 -0.3(10) . . . . ?
S2 N2 C24 C25 18.1(7) . . . . ?
S2 N2 C24 C29 -163.9(4) . . . . ?
C29 C24 C25 C26 1.2(8) . . . . ?
N2 C24 C25 C26 179.1(5) . . . . ?
C24 C25 C26 C27 -2.6(9) . . . . ?
C25 C26 C27 C28 1.5(10) . . . . ?
C26 C27 C28 C29 1.0(10) . . . . ?
C27 C28 C29 C24 -2.2(8) . . . . ?
C27 C28 C29 C30 176.4(5) . . . . ?
C25 C24 C29 C28 1.1(7) . . . . ?
N2 C24 C29 C28 -176.8(5) . . . . ?
C25 C24 C29 C30 -177.5(5) . . . . ?
N2 C24 C29 C30 4.5(7) . . . . ?
C28 C29 C30 C31 -82.6(7) . . . . ?
C24 C29 C30 C31 96.0(6) . . . . ?
C28 C29 C30 C34 95.7(6) . . . . ?
C24 C29 C30 C34 -85.7(6) . . . . ?
C34 C30 C31 C32 2.0(13) . . . . ?
C29 C30 C31 C32 -179.8(9) . . . . ?
C34 C30 C31 C33 177.0(8) . . . . ?
C29 C30 C31 C33 -4.9(12) . . . . ?
C30 C31 C32 C33 176.9(11) . . . . ?
C30 C31 C33 C32 -177.2(10) . . . . ?
C31 C30 C34 C35 177.5(5) . . . . ?
C29 C30 C34 C35 -0.7(7) . . . . ?
C31 C30 C34 C39 -2.8(8) . . . . ?
C29 C30 C34 C39 179.1(5) . . . . ?
C39 C34 C35 C36 2.0(7) . . . . ?
C30 C34 C35 C36 -178.3(5) . . . . ?
C34 C35 C36 C37 -0.5(8) . . . . ?
C35 C36 C37 C38 -1.1(8) . . . . ?
C35 C36 C37 Br1 178.3(4) . . . . ?
C36 C37 C38 C39 1.2(9) . . . . ?
Br1 C37 C38 C39 -178.2(4) . . . . ?
C37 C38 C39 C34 0.4(9) . . . . ?
C35 C34 C39 C38 -1.9(8) . . . . ?
C30 C34 C39 C38 178.3(5) . . . . ?
O4 S2 C40 C45 8.7(5) . . . . ?
O3 S2 C40 C45 139.0(4) . . . . ?
N2 S2 C40 C45 -108.5(4) . . . . ?
O4 S2 C40 C41 -173.4(4) . . . . ?
O3 S2 C40 C41 -43.1(5) . . . . ?
N2 S2 C40 C41 69.4(5) . . . . ?
C45 C40 C41 C42 -0.4(8) . . . . ?
S2 C40 C41 C42 -178.3(4) . . . . ?
C40 C41 C42 C43 0.1(9) . . . . ?
C41 C42 C43 C44 0.1(9) . . . . ?
C41 C42 C43 C46 177.8(6) . . . . ?
C42 C43 C44 C45 -0.1(8) . . . . ?
C46 C43 C44 C45 -177.8(5) . . . . ?
C41 C40 C45 C44 0.4(8) . . . . ?
S2 C40 C45 C44 178.3(4) . . . . ?
C43 C44 C45 C40 -0.2(8) . . . . ?

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
N2 H2A O3 0.86(4) 2.17(4) 2.998(6) 161(4) 2_666
N1 H1 O2 0.79(5) 2.25(5) 3.006(6) 161(5) 2_757
C25 H25 O4 0.93 2.38 3.026(6) 126.9 .
C2 H2 O1 0.93 2.39 3.040(7) 127.1 .
N2 H2A O3 0.86(4) 2.17(4) 2.998(6) 161(4) 2_666
N1 H1 O2 0.79(5) 2.25(5) 3.006(6) 161(5) 2_757
C25 H25 O4 0.93 2.38 3.026(6) 126.9 .
C2 H2 O1 0.93 2.39 3.040(7) 127.1 .
C2 H2 O1 0.93 2.39 3.040(7) 127.1 .
C25 H25 O4 0.93 2.38 3.026(6) 126.9 .
N1 H1 O2 0.79(5) 2.25(5) 3.006(6) 161(5) 2_757
N2 H2A O3 0.86(4) 2.17(4) 2.998(6) 161(4) 2_666
C2 H2 O1 0.93 2.39 3.040(7) 127.1 .
C25 H25 O4 0.93 2.38 3.026(6) 126.9 .
N1 H1 O2 0.79(5) 2.25(5) 3.006(6) 161(5) 2_757
N2 H2A O3 0.86(4) 2.17(4) 2.998(6) 161(4) 2_666

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.066

_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_dm17429_0m
_database_code_depnum_ccdc_archive 'CCDC 1580620'
_audit_update_record             
;
2017-10-18 deposited with the CCDC.
2018-05-21 downloaded from the CCDC.
;
_audit_creation_date             2017-10-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H23 N O2 S'
_chemical_formula_sum            'C26 H23 N O2 S'
_chemical_formula_weight         413.51
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.447(4)
_cell_length_b                   10.559(5)
_cell_length_c                   12.512(6)
_cell_angle_alpha                76.431(8)
_cell_angle_beta                 77.755(9)
_cell_angle_gamma                64.585(7)
_cell_volume                     1087.1(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    786
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.72
_cell_measurement_theta_min      2.406
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0760 before and 0.0574 after correction. The Ratio of minimum to maximum transmission is 0.7293. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_av_unetI/netI     0.1041
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7474
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_min         1.688
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1675
_reflns_number_total             3975
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3975
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1889
_refine_ls_R_factor_gt           0.0964
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1541P)²+0.0686P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2442
_refine_ls_wR_factor_ref         0.3157
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.7712(2) 0.44278(18) 0.77885(16) 0.1046(7) Uani 1 1 d . . . . .
O1 O 0.6797(6) 0.5517(5) 0.8404(5) 0.147(2) Uani 1 1 d . . . . .
O2 O 0.9308(6) 0.4214(5) 0.7389(5) 0.1402(19) Uani 1 1 d . . . . .
N1 N 0.6925(8) 0.4737(6) 0.6611(6) 0.123(2) Uani 1 1 d . . . . .
C1 C 0.7772(10) 0.3701(9) 0.5838(6) 0.120(2) Uani 1 1 d . . . . .
C2 C 0.9295(10) 0.3603(11) 0.5198(10) 0.151(3) Uani 1 1 d . . . . .
H2 H 0.979485 0.413851 0.531832 0.182 Uiso 1 1 calc R . . . .
C3 C 0.9963(10) 0.2738(12) 0.4441(8) 0.141(3) Uani 1 1 d . . . . .
H3 H 1.087022 0.273935 0.397446 0.170 Uiso 1 1 calc R . . . .
C4 C 0.9314(13) 0.1882(10) 0.4367(8) 0.149(3) Uani 1 1 d . . . . .
H4 H 0.983547 0.122854 0.388202 0.179 Uiso 1 1 calc R . . . .
C5 C 0.7822(9) 0.1905(9) 0.5005(6) 0.113(2) Uani 1 1 d . . . . .
H5 H 0.739950 0.129370 0.491347 0.135 Uiso 1 1 calc R . . . .
C6 C 0.7056(8) 0.2832(7) 0.5735(6) 0.0944(19) Uani 1 1 d . . . . .
C7 C 0.5507(7) 0.2938(6) 0.6443(4) 0.0748(14) Uani 1 1 d . . . . .
C8 C 0.4648(9) 0.4041(7) 0.6904(6) 0.0949(18) Uani 1 1 d . . . . .
C9 C 0.5264(10) 0.5227(6) 0.6732(8) 0.132(3) Uani 1 1 d . . . . .
H9A H 0.488222 0.590160 0.607620 0.159 Uiso 1 1 calc R . . . .
H9B H 0.482141 0.572996 0.736031 0.159 Uiso 1 1 calc R . . . .
C10 C 0.3147(9) 0.4257(6) 0.7583(6) 0.0987(19) Uani 1 1 d . . . . .
H10 H 0.276561 0.356289 0.763764 0.118 Uiso 1 1 calc R . . . .
C11 C 0.2259(10) 0.5299(8) 0.8129(7) 0.113(2) Uani 1 1 d . . . . .
C12 C 0.2050(10) 0.6607(9) 0.8427(8) 0.148(3) Uani 1 1 d . . . . .
H12A H 0.180738 0.745014 0.786342 0.178 Uiso 1 1 calc R . . . .
H12B H 0.265764 0.656216 0.898070 0.178 Uiso 1 1 calc R . . . .
C13 C 0.0923(13) 0.5933(11) 0.8756(9) 0.159(3) Uani 1 1 d . . . . .
H13A H 0.080349 0.549666 0.952422 0.190 Uiso 1 1 calc R . . . .
H13B H -0.004267 0.638037 0.841233 0.190 Uiso 1 1 calc R . . . .
C14 C 0.5063(6) 0.1698(5) 0.6563(4) 0.0725(13) Uani 1 1 d . . . . .
C15 C 0.5987(7) 0.0381(6) 0.7074(5) 0.0837(15) Uani 1 1 d . . . . .
H15 H 0.687372 0.026249 0.736259 0.100 Uiso 1 1 calc R . . . .
C16 C 0.5607(8) -0.0777(6) 0.7164(5) 0.0940(18) Uani 1 1 d . . . . .
H16 H 0.624496 -0.166366 0.751216 0.113 Uiso 1 1 calc R . . . .
C17 C 0.4321(9) -0.0634(7) 0.6753(6) 0.0997(19) Uani 1 1 d . . . . .
H17 H 0.407550 -0.141437 0.681586 0.120 Uiso 1 1 calc R . . . .
C18 C 0.3384(8) 0.0680(8) 0.6242(6) 0.109(2) Uani 1 1 d . . . . .
H18 H 0.250061 0.078802 0.595464 0.131 Uiso 1 1 calc R . . . .
C19 C 0.3739(7) 0.1837(6) 0.6152(5) 0.0897(16) Uani 1 1 d . . . . .
H19 H 0.308640 0.272250 0.581279 0.108 Uiso 1 1 calc R . . . .
C20 C 0.7673(7) 0.2806(6) 0.8552(5) 0.0771(15) Uani 1 1 d . . . . .
C21 C 0.8923(7) 0.1543(6) 0.8355(5) 0.0869(15) Uani 1 1 d . . . . .
H21 H 0.978454 0.155073 0.783510 0.104 Uiso 1 1 calc R . . . .
C22 C 0.8884(7) 0.0276(6) 0.8933(5) 0.0907(16) Uani 1 1 d . . . . .
H22 H 0.972405 -0.057095 0.879445 0.109 Uiso 1 1 calc R . . . .
C23 C 0.7623(7) 0.0237(6) 0.9715(5) 0.0854(16) Uani 1 1 d . . . . .
C24 C 0.6398(7) 0.1526(8) 0.9877(5) 0.0940(17) Uani 1 1 d . . . . .
H24 H 0.552776 0.153008 1.039250 0.113 Uiso 1 1 calc R . . . .
C25 C 0.6417(7) 0.2791(7) 0.9311(5) 0.0892(16) Uani 1 1 d . . . . .
H25 H 0.557347 0.363842 0.944378 0.107 Uiso 1 1 calc R . . . .
C26 C 0.7592(8) -0.1136(7) 1.0350(6) 0.122(2) Uani 1 1 d . . . . .
H26A H 0.686234 -0.096542 1.101551 0.182 Uiso 1 1 calc GR . . . .
H26B H 0.862917 -0.176193 1.053865 0.182 Uiso 1 1 calc GR . . . .
H26C H 0.726540 -0.156425 0.990476 0.182 Uiso 1 1 calc GR . . . .


_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 O1 1.394(5) . ?
S1 O2 1.420(5) . ?
S1 N1 1.691(7) . ?
S1 C20 1.766(6) . ?
N1 C1 1.481(10) . ?
N1 C9 1.411(8) . ?
C1 C2 1.464(11) . ?
C1 C6 1.393(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.337(12) . ?
C3 H3 0.9300 . ?
C3 C4 1.319(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.458(11) . ?
C5 H5 0.9300 . ?
C5 C6 1.359(9) . ?
C6 C7 1.515(8) . ?
C7 C8 1.285(8) . ?
C7 C14 1.506(7) . ?
C8 C9 1.549(8) . ?
C8 C10 1.445(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10 0.9300 . ?
C10 C11 1.303(9) . ?
C11 C12 1.436(10) . ?
C11 C13 1.326(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.462(10) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.372(7) . ?
C14 C19 1.389(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.390(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.354(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(9) . ?
C18 H18 0.9300 . ?
C18 C19 1.375(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.383(7) . ?
C20 C25 1.357(8) . ?
C21 H21 0.9300 . ?
C21 C22 1.375(8) . ?
C22 H22 0.9300 . ?
C22 C23 1.381(8) . ?
C23 C24 1.382(8) . ?
C23 C26 1.490(8) . ?
C24 H24 0.9300 . ?
C24 C25 1.363(8) . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
O1 S1 O2 118.9(3) . . ?
O1 S1 N1 109.7(4) . . ?
O1 S1 C20 109.4(3) . . ?
O2 S1 N1 102.7(4) . . ?
O2 S1 C20 108.4(3) . . ?
N1 S1 C20 107.0(2) . . ?
C1 N1 S1 117.1(5) . . ?
C9 N1 S1 115.5(6) . . ?
C9 N1 C1 114.4(6) . . ?
C2 C1 N1 121.3(7) . . ?
C6 C1 N1 117.4(7) . . ?
C6 C1 C2 121.4(9) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(9) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.0(9) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 118.3 . . ?
C3 C4 C5 123.5(10) . . ?
C5 C4 H4 118.3 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.2(8) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C7 119.4(7) . . ?
C5 C6 C1 117.1(7) . . ?
C5 C6 C7 123.5(6) . . ?
C8 C7 C6 120.4(5) . . ?
C8 C7 C14 123.4(5) . . ?
C14 C7 C6 116.2(5) . . ?
C7 C8 C9 118.0(7) . . ?
C7 C8 C10 124.9(5) . . ?
C10 C8 C9 117.1(7) . . ?
N1 C9 C8 114.4(5) . . ?
N1 C9 H9A 108.7 . . ?
N1 C9 H9B 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C8 C10 H10 115.8 . . ?
C11 C10 C8 128.4(7) . . ?
C11 C10 H10 115.8 . . ?
C10 C11 C12 147.1(8) . . ?
C10 C11 C13 149.0(9) . . ?
C13 C11 C12 63.8(6) . . ?
C11 C12 H12A 118.3 . . ?
C11 C12 H12B 118.3 . . ?
C11 C12 C13 54.4(5) . . ?
H12A C12 H12B 115.6 . . ?
C13 C12 H12A 118.3 . . ?
C13 C12 H12B 118.3 . . ?
C11 C13 C12 61.8(6) . . ?
C11 C13 H13A 117.6 . . ?
C11 C13 H13B 117.6 . . ?
C12 C13 H13A 117.6 . . ?
C12 C13 H13B 117.6 . . ?
H13A C13 H13B 114.7 . . ?
C15 C14 C7 120.1(5) . . ?
C15 C14 C19 118.1(4) . . ?
C19 C14 C7 121.8(5) . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.5(5) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.0(6) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 119.1(5) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.6(6) . . ?
C19 C18 H18 119.7 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.7(6) . . ?
C18 C19 H19 119.6 . . ?
C21 C20 S1 119.4(5) . . ?
C25 C20 S1 120.5(5) . . ?
C25 C20 C21 120.0(5) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.6(5) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 H22 119.4 . . ?
C21 C22 C23 121.3(5) . . ?
C23 C22 H22 119.4 . . ?
C22 C23 C24 116.9(5) . . ?
C22 C23 C26 121.2(6) . . ?
C24 C23 C26 121.9(6) . . ?
C23 C24 H24 118.7 . . ?
C25 C24 C23 122.5(6) . . ?
C25 C24 H24 118.7 . . ?
C20 C25 C24 119.6(6) . . ?
C20 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_d8v17381_0m
_database_code_depnum_ccdc_archive 'CCDC 1575471'
_audit_update_record             
;
2017-09-20 deposited with the CCDC.
2018-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H23 N O2 S'
_chemical_formula_weight         413.51

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/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                   11.7526(16)
_cell_length_b                   13.4984(19)
_cell_length_c                   13.5265(19)
_cell_angle_alpha                90
_cell_angle_beta                 92.440(4)
_cell_angle_gamma                90
_cell_volume                     2143.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3914
_cell_measurement_theta_min      4.598
_cell_measurement_theta_max      52.037

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.174
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6181
_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            27670
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_av_R_equivalents  0.1055
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_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         2.132
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             3758
_reflns_number_gt                1875
_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       '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)+(0.1064P)²+0.9552P] 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       0.0015(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3758
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1633
_refine_ls_R_factor_gt           0.0757
_refine_ls_wR_factor_ref         0.2426
_refine_ls_wR_factor_gt          0.1824
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.18845(11) 0.76307(11) 0.33500(11) 0.0821(6) Uani 1 1 d . . . . .
N1 N 0.2474(3) 0.8600(3) 0.3914(3) 0.0771(12) Uani 1 1 d . . . . .
O1 O 0.1545(3) 0.7962(3) 0.2379(3) 0.1122(14) Uani 1 1 d . . . . .
O2 O 0.1067(3) 0.7256(3) 0.3993(3) 0.1019(13) Uani 1 1 d . . . . .
C1 C 0.2929(4) 0.8453(3) 0.4906(4) 0.0665(13) Uani 1 1 d . . . . .
C2 C 0.2219(5) 0.8345(4) 0.5694(4) 0.0811(15) Uani 1 1 d . . . . .
H2 H 0.1433 0.8338 0.5580 0.097 Uiso 1 1 calc R U . . .
C3 C 0.2675(5) 0.8249(4) 0.6644(4) 0.0871(17) Uani 1 1 d . . . . .
H3 H 0.2195 0.8187 0.7169 0.105 Uiso 1 1 calc R U . . .
C4 C 0.3836(5) 0.8245(4) 0.6822(4) 0.0823(15) Uani 1 1 d . . . . .
H4 H 0.4138 0.8182 0.7466 0.099 Uiso 1 1 calc R U . . .
C5 C 0.4552(4) 0.8334(4) 0.6042(4) 0.0733(14) Uani 1 1 d . . . . .
H5 H 0.5336 0.8321 0.6165 0.088 Uiso 1 1 calc R U . . .
C6 C 0.4113(4) 0.8443(3) 0.5069(3) 0.0644(12) Uani 1 1 d . . . . .
C7 C 0.4852(4) 0.8586(3) 0.4225(3) 0.0618(12) Uani 1 1 d . . . . .
C8 C 0.4408(4) 0.8976(4) 0.3376(4) 0.0689(13) Uani 1 1 d . . . . .
C9 C 0.3185(4) 0.9259(4) 0.3332(4) 0.0764(14) Uani 1 1 d . . . . .
H9A H 0.3113 0.9932 0.3575 0.092 Uiso 1 1 calc R U . . .
H9B H 0.2904 0.9250 0.2647 0.092 Uiso 1 1 calc R U . . .
C10 C 0.4991(5) 0.9147(4) 0.2469(4) 0.0830(15) Uani 1 1 d . . . . .
C11 C 0.6130(6) 0.9082(6) 0.2142(5) 0.129(3) Uani 1 1 d . . . . .
H11A H 0.6428 0.8412 0.2138 0.154 Uiso 1 1 calc R U . . .
H11B H 0.6659 0.9528 0.2487 0.154 Uiso 1 1 calc R U . . .
C12 C 0.5698(5) 0.9470(5) 0.1078(5) 0.113(2) Uani 1 1 d . . . . .
H12A H 0.6003 1.0108 0.0891 0.135 Uiso 1 1 calc R U . . .
H12B H 0.5739 0.8988 0.0549 0.135 Uiso 1 1 calc R U . . .
C13 C 0.4609(6) 0.9512(6) 0.1550(5) 0.118(2) Uani 1 1 d . . . . .
H13 H 0.3891 0.9716 0.1315 0.142 Uiso 1 1 calc R U . . .
C14 C 0.6060(4) 0.8271(4) 0.4372(3) 0.0660(13) Uani 1 1 d . . . . .
C15 C 0.6942(5) 0.8937(5) 0.4422(4) 0.0874(16) Uani 1 1 d . . . . .
H15 H 0.6785 0.9611 0.4373 0.105 Uiso 1 1 calc R U . . .
C16 C 0.8053(6) 0.8628(7) 0.4543(4) 0.107(2) Uani 1 1 d . . . . .
H16 H 0.8638 0.9092 0.4578 0.128 Uiso 1 1 calc R U . . .
C17 C 0.8300(5) 0.7658(7) 0.4611(4) 0.109(2) Uani 1 1 d . . . . .
H17 H 0.9054 0.7452 0.4673 0.131 Uiso 1 1 calc R U . . .
C18 C 0.7437(6) 0.6969(6) 0.4589(5) 0.114(2) Uani 1 1 d . . . . .
H18 H 0.7602 0.6298 0.4656 0.137 Uiso 1 1 calc R U . . .
C19 C 0.6329(5) 0.7284(4) 0.4465(4) 0.0886(17) Uani 1 1 d . . . . .
H19 H 0.5746 0.6817 0.4444 0.106 Uiso 1 1 calc R U . . .
C20 C 0.2941(4) 0.6718(4) 0.3223(4) 0.0693(13) Uani 1 1 d . . . . .
C21 C 0.3160(4) 0.6060(4) 0.3985(4) 0.0780(15) Uani 1 1 d . . . . .
H21 H 0.2752 0.6093 0.4558 0.094 Uiso 1 1 calc R U . . .
C22 C 0.3995(5) 0.5347(4) 0.3886(4) 0.0875(16) Uani 1 1 d . . . . .
H22 H 0.4122 0.4889 0.4393 0.105 Uiso 1 1 calc R U . . .
C23 C 0.4635(5) 0.5295(5) 0.3074(5) 0.0904(17) Uani 1 1 d . . . . .
C24 C 0.4398(5) 0.5965(5) 0.2325(5) 0.0980(19) Uani 1 1 d . . . . .
H24 H 0.4817 0.5937 0.1757 0.118 Uiso 1 1 calc R U . . .
C25 C 0.3561(5) 0.6675(5) 0.2387(4) 0.0853(16) Uani 1 1 d . . . . .
H25 H 0.3418 0.7118 0.1870 0.102 Uiso 1 1 calc R U . . .
C26 C 0.5577(5) 0.4546(5) 0.2982(6) 0.131(3) Uani 1 1 d . . . . .
H26A H 0.5694 0.4421 0.2296 0.197 Uiso 1 1 calc R U . . .
H26B H 0.5370 0.3941 0.3301 0.197 Uiso 1 1 calc R U . . .
H26C H 0.6266 0.4800 0.3293 0.197 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 O2 1.417(4) . ?
S1 O1 1.429(4) . ?
S1 N1 1.652(5) . ?
S1 C20 1.763(5) . ?
N1 C1 1.438(6) . ?
N1 C9 1.471(6) . ?
C1 C2 1.389(6) . ?
C1 C6 1.400(6) . ?
C2 C3 1.377(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.476(6) . ?
C7 C8 1.348(6) . ?
C7 C14 1.486(6) . ?
C8 C10 1.450(7) . ?
C8 C9 1.486(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C13 1.394(8) . ?
C10 C11 1.430(8) . ?
C11 C12 1.595(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.456(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13 0.9300 . ?
C14 C15 1.371(7) . ?
C14 C19 1.375(7) . ?
C15 C16 1.374(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.343(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(8) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C25 1.372(7) . ?
C20 C21 1.377(7) . ?
C21 C22 1.384(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.360(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.378(8) . ?
C23 C26 1.508(8) . ?
C24 C25 1.379(8) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
O2 S1 O1 120.4(2) . . ?
O2 S1 N1 106.3(2) . . ?
O1 S1 N1 105.8(2) . . ?
O2 S1 C20 108.0(3) . . ?
O1 S1 C20 107.4(3) . . ?
N1 S1 C20 108.4(2) . . ?
C1 N1 C9 112.7(4) . . ?
C1 N1 S1 116.9(3) . . ?
C9 N1 S1 117.9(3) . . ?
C2 C1 C6 120.2(5) . . ?
C2 C1 N1 121.3(4) . . ?
C6 C1 N1 118.4(4) . . ?
C3 C2 C1 120.2(5) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.5(5) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.8(5) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 121.0(5) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.2(4) . . ?
C5 C6 C7 122.4(4) . . ?
C1 C6 C7 119.4(4) . . ?
C8 C7 C6 119.4(4) . . ?
C8 C7 C14 123.9(4) . . ?
C6 C7 C14 116.7(4) . . ?
C7 C8 C10 127.1(5) . . ?
C7 C8 C9 118.3(4) . . ?
C10 C8 C9 114.6(5) . . ?
N1 C9 C8 113.1(4) . . ?
N1 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
N1 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C13 C10 C11 91.0(5) . . ?
C13 C10 C8 131.7(6) . . ?
C11 C10 C8 137.3(6) . . ?
C10 C11 C12 89.6(5) . . ?
C10 C11 H11A 113.7 . . ?
C12 C11 H11A 113.7 . . ?
C10 C11 H11B 113.7 . . ?
C12 C11 H11B 113.7 . . ?
H11A C11 H11B 111.0 . . ?
C13 C12 C11 82.4(5) . . ?
C13 C12 H12A 114.9 . . ?
C11 C12 H12A 114.9 . . ?
C13 C12 H12B 114.9 . . ?
C11 C12 H12B 114.9 . . ?
H12A C12 H12B 112.0 . . ?
C10 C13 C12 97.0(6) . . ?
C10 C13 H13 131.5 . . ?
C12 C13 H13 131.5 . . ?
C15 C14 C19 117.4(5) . . ?
C15 C14 C7 122.3(5) . . ?
C19 C14 C7 120.3(4) . . ?
C14 C15 C16 121.3(6) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C17 C16 C15 120.3(6) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.1(6) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 119.2(7) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C14 121.7(6) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?
C25 C20 C21 120.1(5) . . ?
C25 C20 S1 120.7(4) . . ?
C21 C20 S1 119.2(4) . . ?
C20 C21 C22 119.1(5) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C23 C22 C21 122.2(6) . . ?
C23 C22 H22 118.9 . . ?
C21 C22 H22 118.9 . . ?
C22 C23 C24 117.3(6) . . ?
C22 C23 C26 122.3(7) . . ?
C24 C23 C26 120.4(7) . . ?
C23 C24 C25 122.2(5) . . ?
C23 C24 H24 118.9 . . ?
C25 C24 H24 118.9 . . ?
C20 C25 C24 119.0(6) . . ?
C20 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
O2 S1 N1 C1 52.9(4) . . . . ?
O1 S1 N1 C1 -177.9(3) . . . . ?
C20 S1 N1 C1 -63.0(4) . . . . ?
O2 S1 N1 C9 -167.6(3) . . . . ?
O1 S1 N1 C9 -38.5(4) . . . . ?
C20 S1 N1 C9 76.5(4) . . . . ?
C9 N1 C1 C2 145.1(5) . . . . ?
S1 N1 C1 C2 -73.4(5) . . . . ?
C9 N1 C1 C6 -33.4(6) . . . . ?
S1 N1 C1 C6 108.2(4) . . . . ?
C6 C1 C2 C3 1.3(8) . . . . ?
N1 C1 C2 C3 -177.1(5) . . . . ?
C1 C2 C3 C4 -0.9(8) . . . . ?
C2 C3 C4 C5 -0.2(8) . . . . ?
C3 C4 C5 C6 0.9(8) . . . . ?
C4 C5 C6 C1 -0.5(7) . . . . ?
C4 C5 C6 C7 177.2(4) . . . . ?
C2 C1 C6 C5 -0.6(7) . . . . ?
N1 C1 C6 C5 177.8(4) . . . . ?
C2 C1 C6 C7 -178.4(4) . . . . ?
N1 C1 C6 C7 0.1(7) . . . . ?
C5 C6 C7 C8 -160.2(5) . . . . ?
C1 C6 C7 C8 17.4(7) . . . . ?
C5 C6 C7 C14 20.4(7) . . . . ?
C1 C6 C7 C14 -162.0(4) . . . . ?
C6 C7 C8 C10 -178.4(5) . . . . ?
C14 C7 C8 C10 0.9(8) . . . . ?
C6 C7 C8 C9 0.8(7) . . . . ?
C14 C7 C8 C9 -179.9(4) . . . . ?
C1 N1 C9 C8 49.9(6) . . . . ?
S1 N1 C9 C8 -91.1(5) . . . . ?
C7 C8 C9 N1 -34.2(6) . . . . ?
C10 C8 C9 N1 145.1(4) . . . . ?
C7 C8 C10 C13 177.7(6) . . . . ?
C9 C8 C10 C13 -1.5(9) . . . . ?
C7 C8 C10 C11 -6.5(10) . . . . ?
C9 C8 C10 C11 174.3(7) . . . . ?
C13 C10 C11 C12 -1.5(5) . . . . ?
C8 C10 C11 C12 -178.4(6) . . . . ?
C10 C11 C12 C13 1.4(5) . . . . ?
C11 C10 C13 C12 1.6(6) . . . . ?
C8 C10 C13 C12 178.8(6) . . . . ?
C11 C12 C13 C10 -1.5(5) . . . . ?
C8 C7 C14 C15 69.3(7) . . . . ?
C6 C7 C14 C15 -111.4(5) . . . . ?
C8 C7 C14 C19 -110.9(6) . . . . ?
C6 C7 C14 C19 68.5(6) . . . . ?
C19 C14 C15 C16 1.1(8) . . . . ?
C7 C14 C15 C16 -179.0(5) . . . . ?
C14 C15 C16 C17 0.3(9) . . . . ?
C15 C16 C17 C18 -1.9(10) . . . . ?
C16 C17 C18 C19 2.0(10) . . . . ?
C17 C18 C19 C14 -0.6(9) . . . . ?
C15 C14 C19 C18 -1.0(8) . . . . ?
C7 C14 C19 C18 179.2(5) . . . . ?
O2 S1 C20 C25 153.3(4) . . . . ?
O1 S1 C20 C25 22.0(5) . . . . ?
N1 S1 C20 C25 -91.9(4) . . . . ?
O2 S1 C20 C21 -28.2(5) . . . . ?
O1 S1 C20 C21 -159.5(4) . . . . ?
N1 S1 C20 C21 86.6(4) . . . . ?
C25 C20 C21 C22 -1.2(7) . . . . ?
S1 C20 C21 C22 -179.6(4) . . . . ?
C20 C21 C22 C23 2.2(8) . . . . ?
C21 C22 C23 C24 -2.1(8) . . . . ?
C21 C22 C23 C26 177.5(5) . . . . ?
C22 C23 C24 C25 0.9(9) . . . . ?
C26 C23 C24 C25 -178.6(5) . . . . ?
C21 C20 C25 C24 0.1(8) . . . . ?
S1 C20 C25 C24 178.5(4) . . . . ?
C23 C24 C25 C20 0.1(9) . . . . ?

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
C9 H9B O1 0.97 2.38 2.869(7) 110.8 .

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-4



