# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

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

data_10b
_database_code_depnum_ccdc_archive 'CCDC 1525176'
_audit_update_record             
;
2017-01-02 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H30 N2 O2 S'
_chemical_formula_weight         506.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.0697(3)
_cell_length_b                   32.4621(12)
_cell_length_c                   9.8721(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.5490(17)
_cell_angle_gamma                90
_cell_volume                     2585.97(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      68.49

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.364
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27147
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.722
_diffrn_reflns_theta_max         68.384
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4726
_reflns_number_gt                4143
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4726
_refine_ls_number_parameters     335
_refine_ls_number_restraints     99
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1365
_refine_ls_wR_factor_gt          0.1306
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.44479(5) 0.35542(2) 0.73368(4) 0.02383(15) Uani 1 1 d . U . . .
O2 O 0.39741(17) 0.31530(4) 0.78368(12) 0.0312(3) Uani 1 1 d . U . . .
O1 O 0.55336(16) 0.37941(4) 0.81818(12) 0.0320(3) Uani 1 1 d . U . . .
N2 N 0.53609(17) 0.33885(4) 0.36207(14) 0.0218(3) Uani 1 1 d . U . . .
N1 N 0.53270(18) 0.35399(4) 0.58776(14) 0.0236(3) Uani 1 1 d . U . . .
C2 C -0.0269(2) 0.43043(5) 0.66960(16) 0.0249(4) Uani 1 1 d . U . . .
C20 C 0.2174(2) 0.36451(5) 0.21016(16) 0.0207(3) Uani 1 1 d . U . . .
C8 C 0.4633(2) 0.33519(5) 0.48234(16) 0.0220(3) Uani 1 1 d . U . . .
C5 C 0.2608(2) 0.38433(5) 0.70865(15) 0.0205(3) Uani 1 1 d . U . . .
C27 C 0.0428(2) 0.28323(5) 0.09643(16) 0.0237(4) Uani 1 1 d . U . . .
C6 C 0.2720(2) 0.42597(5) 0.67837(16) 0.0243(4) Uani 1 1 d . U . . .
H6 H 0.3751 0.4385 0.6708 0.029 Uiso 1 1 calc R U . . .
C21 C 0.2585(2) 0.38357(5) 0.08803(16) 0.0267(4) Uani 1 1 d . U . . .
H21 H 0.3206 0.3692 0.0247 0.032 Uiso 1 1 calc R U . . .
C3 C -0.0359(2) 0.38870(5) 0.70067(18) 0.0273(4) Uani 1 1 d . U . . .
H3 H -0.1389 0.3761 0.7085 0.033 Uiso 1 1 calc R U . . .
C4 C 0.1071(2) 0.36566(5) 0.72006(17) 0.0251(4) Uani 1 1 d . U . . .
H4 H 0.0998 0.3378 0.7407 0.030 Uiso 1 1 calc R U . . .
C14 C 0.6531(2) 0.40323(5) 0.27365(17) 0.0246(4) Uani 1 1 d . U . . .
C19 C 0.5627(2) 0.43298(5) 0.34266(18) 0.0276(4) Uani 1 1 d . U . . .
H19 H 0.5235 0.4273 0.4289 0.033 Uiso 1 1 calc R U . . .
C25 C 0.1285(2) 0.38722(5) 0.30413(16) 0.0227(4) Uani 1 1 d . U . . .
H25 H 0.1018 0.3754 0.3869 0.027 Uiso 1 1 calc R U . . .
C11 C 0.4665(2) 0.31838(5) 0.24264(16) 0.0233(4) Uani 1 1 d . U . . .
H11A H 0.5015 0.2898 0.2425 0.028 Uiso 1 1 calc R U . . .
H11B H 0.5101 0.3313 0.1619 0.028 Uiso 1 1 calc R U . . .
C10 C 0.2187(2) 0.30491(5) 0.37294(17) 0.0229(4) Uani 1 1 d . U . . .
H10 H 0.1182 0.2910 0.3786 0.028 Uiso 1 1 calc R U . . .
C9 C 0.3088(2) 0.31090(5) 0.48443(16) 0.0232(4) Uani 1 1 d . U . . .
H9 H 0.2737 0.2995 0.5657 0.028 Uiso 1 1 calc R U . . .
C12 C 0.2766(2) 0.32019(5) 0.23763(16) 0.0213(4) Uani 1 1 d . U . . .
C26 C 0.2249(2) 0.28985(5) 0.12288(17) 0.0253(4) Uani 1 1 d . U . . .
H26A H 0.2741 0.2995 0.0394 0.030 Uiso 1 1 calc R U . . .
H26B H 0.2740 0.2633 0.1434 0.030 Uiso 1 1 calc R U . . .
C7 C 0.1288(2) 0.44869(5) 0.65946(17) 0.0260(4) Uani 1 1 d . U . . .
H7 H 0.1364 0.4766 0.6396 0.031 Uiso 1 1 calc R U . . .
C32 C -0.0467(2) 0.30930(6) 0.01091(17) 0.0297(4) Uani 1 1 d . U . . .
H32 H 0.0031 0.3331 -0.0220 0.036 Uiso 1 1 calc R U . . .
C22 C 0.2083(2) 0.42339(6) 0.05988(17) 0.0301(4) Uani 1 1 d . U . . .
H22 H 0.2358 0.4355 -0.0223 0.036 Uiso 1 1 calc R U . . .
C13 C 0.6891(2) 0.36243(5) 0.34148(18) 0.0251(4) Uani 1 1 d . U . . .
H13A H 0.7642 0.3466 0.2858 0.030 Uiso 1 1 calc R U . . .
H13B H 0.7430 0.3673 0.4283 0.030 Uiso 1 1 calc R U . . .
C23 C 0.1173(2) 0.44537(5) 0.15323(19) 0.0294(4) Uani 1 1 d . U . . .
H23 H 0.0822 0.4720 0.1337 0.035 Uiso 1 1 calc R U . . .
C24 C 0.0789(2) 0.42739(5) 0.27604(18) 0.0267(4) Uani 1 1 d . U . . .
H24 H 0.0197 0.4422 0.3401 0.032 Uiso 1 1 calc R U . . .
C28 C -0.0383(2) 0.24899(5) 0.1483(2) 0.0316(4) Uani 1 1 d . U . . .
H28 H 0.0172 0.2319 0.2093 0.038 Uiso 1 1 calc R U . . .
C31 C -0.2093(3) 0.30032(6) -0.02587(19) 0.0348(4) Uani 1 1 d . U . . .
H31 H -0.2673 0.3180 -0.0833 0.042 Uiso 1 1 calc R U . . .
C30 C -0.2853(2) 0.26525(6) 0.0223(2) 0.0345(4) Uani 1 1 d . U . . .
H30 H -0.3929 0.2588 -0.0047 0.041 Uiso 1 1 calc R U . . .
C29 C -0.2001(3) 0.23981(6) 0.1112(2) 0.0375(5) Uani 1 1 d . U . . .
H29 H -0.2515 0.2165 0.1460 0.045 Uiso 1 1 calc R U . . .
C1 C -0.1834(2) 0.45490(6) 0.6482(2) 0.0349(4) Uani 1 1 d . U . . .
H1A H -0.1688 0.4821 0.6843 0.052 Uiso 1 1 calc R U . . .
H1B H -0.2734 0.4416 0.6935 0.052 Uiso 1 1 calc R U . . .
H1C H -0.2079 0.4566 0.5530 0.052 Uiso 1 1 calc R U . . .
C18 C 0.5308(2) 0.47082(6) 0.2848(2) 0.0341(4) Uani 1 1 d . U . . .
H18 H 0.4715 0.4906 0.3323 0.041 Uiso 1 1 calc R U . . .
C15 C 0.7065(2) 0.41172(6) 0.14352(18) 0.0330(4) Uani 1 1 d . U . . .
H15 H 0.7646 0.3919 0.0953 0.040 Uiso 1 1 calc R U . . .
C16 C 0.6734(3) 0.44982(7) 0.0850(2) 0.0409(5) Uani 1 1 d . U . . .
H16 H 0.7094 0.4554 -0.0023 0.049 Uiso 1 1 calc R U . . .
C17 C 0.5874(3) 0.47933(6) 0.1557(2) 0.0379(5) Uani 1 1 d . U . . .
H17 H 0.5672 0.5050 0.1168 0.045 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 O1 1.4337(14) . ?
S1 O2 1.4457(13) . ?
S1 N1 1.6125(14) . ?
S1 C5 1.7717(17) . ?
N2 C8 1.335(2) . ?
N2 C11 1.461(2) . ?
N2 C13 1.469(2) . ?
N1 C8 1.326(2) . ?
C2 C3 1.391(3) . ?
C2 C7 1.394(2) . ?
C2 C1 1.505(2) . ?
C20 C25 1.390(2) . ?
C20 C21 1.398(2) . ?
C20 C12 1.539(2) . ?
C8 C9 1.475(2) . ?
C5 C4 1.386(2) . ?
C5 C6 1.388(2) . ?
C27 C28 1.390(2) . ?
C27 C32 1.392(3) . ?
C27 C26 1.505(3) . ?
C6 C7 1.382(2) . ?
C21 C22 1.382(3) . ?
C3 C4 1.387(3) . ?
C14 C15 1.387(2) . ?
C14 C19 1.392(3) . ?
C14 C13 1.511(2) . ?
C19 C18 1.378(3) . ?
C25 C24 1.391(2) . ?
C11 C12 1.534(2) . ?
C10 C9 1.328(2) . ?
C10 C12 1.504(2) . ?
C12 C26 1.555(2) . ?
C32 C31 1.389(3) . ?
C22 C23 1.382(3) . ?
C23 C24 1.383(3) . ?
C28 C29 1.385(3) . ?
C31 C30 1.380(3) . ?
C30 C29 1.383(3) . ?
C18 C17 1.386(3) . ?
C15 C16 1.390(3) . ?
C16 C17 1.377(3) . ?

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 116.93(8) . . ?
O1 S1 N1 105.29(8) . . ?
O2 S1 N1 113.52(7) . . ?
O1 S1 C5 107.46(8) . . ?
O2 S1 C5 107.51(8) . . ?
N1 S1 C5 105.42(7) . . ?
C8 N2 C11 120.55(14) . . ?
C8 N2 C13 123.18(14) . . ?
C11 N2 C13 116.26(13) . . ?
C8 N1 S1 121.88(13) . . ?
C3 C2 C7 118.60(16) . . ?
C3 C2 C1 119.98(17) . . ?
C7 C2 C1 121.41(17) . . ?
C25 C20 C21 117.98(15) . . ?
C25 C20 C12 122.66(14) . . ?
C21 C20 C12 119.32(15) . . ?
N1 C8 N2 118.08(15) . . ?
N1 C8 C9 125.85(15) . . ?
N2 C8 C9 116.05(15) . . ?
C4 C5 C6 120.24(16) . . ?
C4 C5 S1 120.42(13) . . ?
C6 C5 S1 119.33(13) . . ?
C28 C27 C32 117.77(17) . . ?
C28 C27 C26 120.83(16) . . ?
C32 C27 C26 121.22(15) . . ?
C7 C6 C5 119.52(16) . . ?
C22 C21 C20 121.05(16) . . ?
C4 C3 C2 120.73(16) . . ?
C5 C4 C3 119.79(16) . . ?
C15 C14 C19 118.96(17) . . ?
C15 C14 C13 121.65(16) . . ?
C19 C14 C13 119.38(15) . . ?
C18 C19 C14 120.82(17) . . ?
C20 C25 C24 120.91(15) . . ?
N2 C11 C12 112.62(13) . . ?
C9 C10 C12 121.05(15) . . ?
C10 C9 C8 121.52(15) . . ?
C10 C12 C11 106.12(14) . . ?
C10 C12 C20 111.48(13) . . ?
C11 C12 C20 110.48(13) . . ?
C10 C12 C26 110.78(13) . . ?
C11 C12 C26 105.08(13) . . ?
C20 C12 C26 112.52(14) . . ?
C27 C26 C12 118.12(14) . . ?
C6 C7 C2 121.11(16) . . ?
C31 C32 C27 120.94(17) . . ?
C23 C22 C21 120.35(16) . . ?
N2 C13 C14 111.09(14) . . ?
C22 C23 C24 119.45(16) . . ?
C23 C24 C25 120.24(16) . . ?
C29 C28 C27 121.34(18) . . ?
C30 C31 C32 120.32(19) . . ?
C31 C30 C29 119.45(18) . . ?
C30 C29 C28 120.07(18) . . ?
C19 C18 C17 119.81(19) . . ?
C14 C15 C16 120.13(19) . . ?
C17 C16 C15 120.27(18) . . ?
C16 C17 C18 119.97(18) . . ?

_refine_diff_density_max         0.509
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.053

_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_30
_database_code_depnum_ccdc_archive 'CCDC 1525179'
_audit_update_record             
;
2017-01-02 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H34 N2 O2 S'
_chemical_formula_weight         582.73

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.375(4)
_cell_length_b                   17.958(7)
_cell_length_c                   14.179(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.594(10)
_cell_angle_gamma                90
_cell_volume                     3150(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    449
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      21.08

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             1398
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.316
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_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       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10213
_diffrn_reflns_av_unetI/netI     0.1902
_diffrn_reflns_av_R_equivalents  0.1130
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.646
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.733
_diffrn_measured_fraction_theta_full 0.764
_diffrn_reflns_Laue_measured_fraction_max 0.733
_diffrn_reflns_Laue_measured_fraction_full 0.764
_diffrn_reflns_point_group_measured_fraction_max 0.733
_diffrn_reflns_point_group_measured_fraction_full 0.764
_reflns_number_total             5734
_reflns_number_gt                2133
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.8470P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5734
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2279
_refine_ls_R_factor_gt           0.0805
_refine_ls_wR_factor_ref         0.2471
_refine_ls_wR_factor_gt          0.1721
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_restrained_S_all      0.912
_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 0.84703(11) 0.42124(7) 0.16028(12) 0.0365(4) Uani 1 1 d . . . . .
O1 O 0.9173(3) 0.4181(2) 0.2422(3) 0.0534(12) Uani 1 1 d . . . . .
O2 O 0.8314(3) 0.49383(19) 0.1181(4) 0.0520(13) Uani 1 1 d . . . . .
N2 N 0.5677(3) 0.3729(2) 0.2454(4) 0.0333(12) Uani 1 1 d . . . . .
N1 N 0.7344(3) 0.3789(2) 0.1795(4) 0.0339(12) Uani 1 1 d . . . . .
C16 C 0.6691(4) 0.4875(3) 0.2698(5) 0.0347(15) Uani 1 1 d . . . . .
H16 H 0.6414 0.5270 0.2344 0.042 Uiso 1 1 calc R U . . .
C15 C 0.6582(4) 0.4110(3) 0.2289(4) 0.0306(13) Uani 1 1 d . . . . .
C9 C 0.3798(4) 0.4168(3) 0.2257(5) 0.0395(16) Uani 1 1 d . . . . .
C2 C 0.5486(4) 0.2435(3) 0.2979(5) 0.0369(16) Uani 1 1 d . . . . .
C32 C 0.8994(4) 0.3614(3) 0.0747(5) 0.0380(15) Uani 1 1 d . . . . .
C26 C 0.7228(4) 0.5821(3) 0.3829(5) 0.0377(14) Uani 1 1 d . . . . .
C1 C 0.5527(4) 0.2952(3) 0.2128(5) 0.0388(15) Uani 1 1 d . . . . .
H1A H 0.6121 0.2810 0.1734 0.047 Uiso 1 1 calc R U . . .
H1B H 0.4861 0.2911 0.1755 0.047 Uiso 1 1 calc R U . . .
C17 C 0.7145(5) 0.5027(3) 0.3513(5) 0.0381(15) Uani 1 1 d . . . . .
C14 C 0.3899(5) 0.4541(3) 0.1411(5) 0.0453(17) Uani 1 1 d . . . . .
H14 H 0.4568 0.4733 0.1253 0.054 Uiso 1 1 calc R U . . .
C7 C 0.4565(5) 0.2026(3) 0.3144(5) 0.0469(17) Uani 1 1 d . . . . .
H7 H 0.3968 0.2069 0.2733 0.056 Uiso 1 1 calc R U . . .
C8 C 0.4746(4) 0.4052(3) 0.2917(4) 0.0386(15) Uani 1 1 d . . . . .
H8A H 0.4954 0.4526 0.3193 0.046 Uiso 1 1 calc R U . . .
H8B H 0.4535 0.3725 0.3425 0.046 Uiso 1 1 calc R U . . .
C20 C 0.8366(7) 0.4510(3) 0.5536(6) 0.060(2) Uani 1 1 d . . . . .
C37 C 0.9071(5) 0.2856(3) 0.0922(5) 0.0513(18) Uani 1 1 d . . . . .
H37 H 0.8809 0.2652 0.1474 0.062 Uiso 1 1 calc R U . . .
C10 C 0.2787(4) 0.3906(3) 0.2503(5) 0.0469(18) Uani 1 1 d . . . . .
H10 H 0.2695 0.3667 0.3077 0.056 Uiso 1 1 calc R U . . .
C27 C 0.7853(5) 0.6315(3) 0.3338(5) 0.0522(19) Uani 1 1 d . . . . .
H27 H 0.8244 0.6148 0.2828 0.063 Uiso 1 1 calc R U . . .
C11 C 0.1914(5) 0.4007(3) 0.1878(6) 0.058(2) Uani 1 1 d . . . . .
H11 H 0.1237 0.3831 0.2036 0.070 Uiso 1 1 calc R U . . .
C21 C 0.7355(6) 0.4342(3) 0.5140(5) 0.0531(18) Uani 1 1 d . . . . .
C35 C 0.9958(5) 0.2694(4) -0.0562(6) 0.056(2) Uani 1 1 d . . . . .
C3 C 0.6369(6) 0.2360(3) 0.3582(6) 0.0548(19) Uani 1 1 d . . . . .
H3 H 0.7002 0.2619 0.3466 0.066 Uiso 1 1 calc R U . . .
C30 C 0.6668(5) 0.6079(3) 0.4585(5) 0.0529(19) Uani 1 1 d . . . . .
H30 H 0.6270 0.5747 0.4939 0.063 Uiso 1 1 calc R U . . .
C13 C 0.3024(5) 0.4634(3) 0.0799(6) 0.0557(19) Uani 1 1 d . . . . .
H13 H 0.3108 0.4882 0.0229 0.067 Uiso 1 1 calc R U . . .
C23 C 0.6749(7) 0.4048(3) 0.6641(7) 0.074(3) Uani 1 1 d . . . . .
H23 H 0.6206 0.3886 0.7033 0.089 Uiso 1 1 calc R U . . .
C33 C 0.9379(4) 0.3918(3) -0.0080(5) 0.0464(16) Uani 1 1 d . . . . .
H33 H 0.9320 0.4426 -0.0202 0.056 Uiso 1 1 calc R U . . .
C28 C 0.7903(5) 0.7060(3) 0.3598(6) 0.059(2) Uani 1 1 d . . . . .
H28 H 0.8347 0.7386 0.3278 0.070 Uiso 1 1 calc R U . . .
C29 C 0.7296(5) 0.7313(3) 0.4328(6) 0.058(2) Uani 1 1 d . . . . .
H29 H 0.7302 0.7817 0.4479 0.070 Uiso 1 1 calc R U . . .
C6 C 0.4519(7) 0.1554(3) 0.3915(6) 0.062(2) Uani 1 1 d . . . . .
H6 H 0.3898 0.1279 0.4021 0.074 Uiso 1 1 calc R U . . .
C34 C 0.9857(5) 0.3437(4) -0.0724(6) 0.062(2) Uani 1 1 d . . . . .
H34 H 1.0115 0.3633 -0.1282 0.074 Uiso 1 1 calc R U . . .
C12 C 0.2035(5) 0.4364(3) 0.1027(6) 0.061(2) Uani 1 1 d . . . . .
H12 H 0.1446 0.4419 0.0611 0.073 Uiso 1 1 calc R U . . .
C22 C 0.6505(6) 0.4107(3) 0.5626(6) 0.072(2) Uani 1 1 d . . . . .
H22 H 0.5835 0.3993 0.5349 0.087 Uiso 1 1 calc R U . . .
C31 C 0.6686(6) 0.6835(3) 0.4833(5) 0.062(2) Uani 1 1 d . . . . .
H31 H 0.6287 0.7007 0.5335 0.074 Uiso 1 1 calc R U . . .
C18 C 0.7653(6) 0.4440(3) 0.4137(5) 0.057(2) Uani 1 1 d . . . . .
H18 H 0.7682 0.3959 0.3811 0.069 Uiso 1 1 calc R U . . .
C36 C 0.9554(5) 0.2403(3) 0.0244(6) 0.060(2) Uani 1 1 d . . . . .
H36 H 0.9599 0.1892 0.0347 0.072 Uiso 1 1 calc R U . . .
C5 C 0.5401(8) 0.1497(4) 0.4520(6) 0.075(2) Uani 1 1 d . . . . .
H5 H 0.5370 0.1183 0.5040 0.091 Uiso 1 1 calc R U . . .
C25 C 0.8606(6) 0.4451(4) 0.6507(6) 0.068(2) Uani 1 1 d . . . . .
H25 H 0.9286 0.4559 0.6768 0.082 Uiso 1 1 calc R U . . .
C24 C 0.7755(8) 0.4222(4) 0.7043(6) 0.076(2) Uani 1 1 d . . . . .
H24 H 0.7856 0.4182 0.7694 0.091 Uiso 1 1 calc R U . . .
C19 C 0.8839(5) 0.4661(4) 0.4608(6) 0.065(2) Uani 1 1 d . . . . .
H19A H 0.9418 0.4324 0.4446 0.078 Uiso 1 1 calc R U . . .
H19B H 0.9046 0.5176 0.4513 0.078 Uiso 1 1 calc R U . . .
C4 C 0.6315(7) 0.1890(4) 0.4375(7) 0.079(3) Uani 1 1 d . . . . .
H4 H 0.6903 0.1849 0.4796 0.095 Uiso 1 1 calc R U . . .
C38 C 1.0498(6) 0.2191(4) -0.1266(7) 0.088(3) Uani 1 1 d . . . . .
H38A H 1.1117 0.1958 -0.0970 0.133 Uiso 1 1 calc R U . . .
H38B H 1.0723 0.2481 -0.1794 0.133 Uiso 1 1 calc R U . . .
H38C H 0.9996 0.1815 -0.1480 0.133 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 O1 1.433(5) . ?
S1 O2 1.445(4) . ?
S1 N1 1.618(4) . ?
S1 C32 1.759(6) . ?
N2 C15 1.339(6) . ?
N2 C8 1.462(6) . ?
N2 C1 1.480(6) . ?
N1 C15 1.322(6) . ?
C16 C17 1.299(9) . ?
C16 C15 1.495(7) . ?
C16 H16 0.9300 . ?
C9 C14 1.383(9) . ?
C9 C10 1.391(7) . ?
C9 C8 1.495(8) . ?
C2 C3 1.376(9) . ?
C2 C7 1.381(7) . ?
C2 C1 1.525(9) . ?
C32 C33 1.389(9) . ?
C32 C37 1.387(7) . ?
C26 C30 1.374(8) . ?
C26 C27 1.378(8) . ?
C26 C17 1.497(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C17 C18 1.504(9) . ?
C14 C13 1.380(9) . ?
C14 H14 0.9300 . ?
C7 C6 1.386(10) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C20 C21 1.389(10) . ?
C20 C25 1.405(10) . ?
C20 C19 1.481(10) . ?
C37 C36 1.406(9) . ?
C37 H37 0.9300 . ?
C10 C11 1.390(9) . ?
C10 H10 0.9300 . ?
C27 C28 1.389(8) . ?
C27 H27 0.9300 . ?
C11 C12 1.377(11) . ?
C11 H11 0.9300 . ?
C21 C22 1.342(9) . ?
C21 C18 1.489(10) . ?
C35 C36 1.364(10) . ?
C35 C34 1.359(8) . ?
C35 C38 1.515(9) . ?
C3 C4 1.409(11) . ?
C3 H3 0.9300 . ?
C30 C31 1.402(7) . ?
C30 H30 0.9300 . ?
C13 C12 1.365(9) . ?
C13 H13 0.9300 . ?
C23 C24 1.390(11) . ?
C23 C22 1.467(11) . ?
C23 H23 0.9300 . ?
C33 C34 1.401(9) . ?
C33 H33 0.9300 . ?
C28 C29 1.374(9) . ?
C28 H28 0.9300 . ?
C29 C31 1.360(8) . ?
C29 H29 0.9300 . ?
C6 C5 1.374(11) . ?
C6 H6 0.9300 . ?
C34 H34 0.9300 . ?
C12 H12 0.9300 . ?
C22 H22 0.9300 . ?
C31 H31 0.9300 . ?
C18 C19 1.644(10) . ?
C18 H18 0.9800 . ?
C36 H36 0.9300 . ?
C5 C4 1.353(10) . ?
C5 H5 0.9300 . ?
C25 C24 1.380(10) . ?
C25 H25 0.9300 . ?
C24 H24 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C4 H4 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 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 116.2(3) . . ?
O1 S1 N1 110.6(3) . . ?
O2 S1 N1 112.8(2) . . ?
O1 S1 C32 108.0(3) . . ?
O2 S1 C32 108.3(3) . . ?
N1 S1 C32 99.5(2) . . ?
C15 N2 C8 123.3(4) . . ?
C15 N2 C1 121.7(4) . . ?
C8 N2 C1 114.9(4) . . ?
C15 N1 S1 120.9(3) . . ?
C17 C16 C15 124.8(5) . . ?
C17 C16 H16 117.6 . . ?
C15 C16 H16 117.6 . . ?
N1 C15 N2 118.8(4) . . ?
N1 C15 C16 123.3(4) . . ?
N2 C15 C16 117.9(4) . . ?
C14 C9 C10 119.0(6) . . ?
C14 C9 C8 121.5(5) . . ?
C10 C9 C8 119.5(6) . . ?
C3 C2 C7 119.2(6) . . ?
C3 C2 C1 120.5(5) . . ?
C7 C2 C1 120.2(6) . . ?
C33 C32 C37 121.0(6) . . ?
C33 C32 S1 118.9(4) . . ?
C37 C32 S1 120.1(5) . . ?
C30 C26 C27 118.7(5) . . ?
C30 C26 C17 121.5(5) . . ?
C27 C26 C17 119.7(5) . . ?
N2 C1 C2 109.5(5) . . ?
N2 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
N2 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
C16 C17 C26 119.5(5) . . ?
C16 C17 C18 122.6(5) . . ?
C26 C17 C18 117.9(6) . . ?
C9 C14 C13 121.1(6) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C6 C7 C2 120.7(7) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
N2 C8 C9 112.8(5) . . ?
N2 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N2 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C21 C20 C25 123.0(7) . . ?
C21 C20 C19 93.1(7) . . ?
C25 C20 C19 143.8(8) . . ?
C32 C37 C36 118.3(7) . . ?
C32 C37 H37 120.8 . . ?
C36 C37 H37 120.8 . . ?
C9 C10 C11 119.0(6) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C26 C27 C28 120.5(6) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C12 C11 C10 121.2(6) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C22 C21 C20 124.7(8) . . ?
C22 C21 C18 138.2(8) . . ?
C20 C21 C18 96.7(6) . . ?
C36 C35 C34 118.9(6) . . ?
C36 C35 C38 120.2(7) . . ?
C34 C35 C38 120.9(7) . . ?
C2 C3 C4 120.0(7) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C26 C30 C31 121.1(6) . . ?
C26 C30 H30 119.4 . . ?
C31 C30 H30 119.4 . . ?
C14 C13 C12 120.0(7) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C24 C23 C22 122.9(7) . . ?
C24 C23 H23 118.5 . . ?
C22 C23 H23 118.5 . . ?
C32 C33 C34 117.9(6) . . ?
C32 C33 H33 121.0 . . ?
C34 C33 H33 121.0 . . ?
C29 C28 C27 119.9(6) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C28 C29 C31 120.7(6) . . ?
C28 C29 H29 119.6 . . ?
C31 C29 H29 119.6 . . ?
C5 C6 C7 119.3(7) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C35 C34 C33 122.3(7) . . ?
C35 C34 H34 118.9 . . ?
C33 C34 H34 118.9 . . ?
C13 C12 C11 119.6(7) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C21 C22 C23 112.6(8) . . ?
C21 C22 H22 123.7 . . ?
C23 C22 H22 123.7 . . ?
C29 C31 C30 119.0(6) . . ?
C29 C31 H31 120.5 . . ?
C30 C31 H31 120.5 . . ?
C21 C18 C17 122.3(6) . . ?
C21 C18 C19 83.3(5) . . ?
C17 C18 C19 115.1(5) . . ?
C21 C18 H18 111.1 . . ?
C17 C18 H18 111.1 . . ?
C19 C18 H18 111.1 . . ?
C35 C36 C37 121.6(6) . . ?
C35 C36 H36 119.2 . . ?
C37 C36 H36 119.2 . . ?
C4 C5 C6 121.3(8) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C24 C25 C20 114.7(8) . . ?
C24 C25 H25 122.6 . . ?
C20 C25 H25 122.6 . . ?
C23 C24 C25 122.0(9) . . ?
C23 C24 H24 119.0 . . ?
C25 C24 H24 119.0 . . ?
C20 C19 C18 86.9(5) . . ?
C20 C19 H19A 114.2 . . ?
C18 C19 H19A 114.2 . . ?
C20 C19 H19B 114.2 . . ?
C18 C19 H19B 114.2 . . ?
H19A C19 H19B 111.3 . . ?
C5 C4 C3 119.4(8) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

_refine_diff_density_max         0.463
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.054

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_22b
_database_code_depnum_ccdc_archive 'CCDC 1525178'
_audit_update_record             
;
2017-01-02 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H29 N3 O2 S'
_chemical_formula_weight         531.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   8.7353(11)
_cell_length_b                   10.2521(13)
_cell_length_c                   15.765(2)
_cell_angle_alpha                101.925(6)
_cell_angle_beta                 98.258(6)
_cell_angle_gamma                93.270(5)
_cell_volume                     1361.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      77.26

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.334
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16897
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.902
_diffrn_reflns_theta_max         77.283
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5550
_reflns_number_gt                4453
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5550
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1123
_refine_ls_R_factor_gt           0.0948
_refine_ls_wR_factor_ref         0.2636
_refine_ls_wR_factor_gt          0.2521
_refine_ls_goodness_of_fit_ref   1.782
_refine_ls_restrained_S_all      1.782
_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
S001 S 0.23013(8) 0.29694(8) 0.08385(5) 0.0224(3) Uani 1 1 d . . . . .
O002 O 0.3206(2) 0.2891(2) 0.01356(16) 0.0275(5) Uani 1 1 d . . . . .
O003 O 0.1292(2) 0.1809(2) 0.08184(17) 0.0290(6) Uani 1 1 d . . . . .
N004 N 0.1229(3) 0.4203(3) 0.09263(18) 0.0221(6) Uani 1 1 d . . . . .
N005 N 0.0867(3) 0.6438(3) 0.11412(18) 0.0206(6) Uani 1 1 d . . . . .
C006 C 0.3622(3) 0.3306(3) 0.1836(2) 0.0215(7) Uani 1 1 d . . . . .
C007 C -0.0681(3) 0.6541(3) 0.2335(2) 0.0195(7) Uani 1 1 d . . . . .
C008 C 0.1781(3) 0.5450(3) 0.0932(2) 0.0196(7) Uani 1 1 d . . . . .
C009 C 0.3323(3) 0.5862(3) 0.0751(2) 0.0208(7) Uani 1 1 d . . . . .
H009 H 0.3849 0.5248 0.0407 0.025 Uiso 1 1 calc R U . . .
C00A C 0.3078(4) 0.3222(3) 0.2608(2) 0.0259(7) Uani 1 1 d . . . . .
H00A H 0.2038 0.2956 0.2597 0.031 Uiso 1 1 calc R U . . .
C00B C -0.1597(3) 0.7514(3) 0.2690(2) 0.0230(7) Uani 1 1 d . . . . .
H00B H -0.2206 0.7952 0.2324 0.028 Uiso 1 1 calc R U . . .
C00C C -0.0698(3) 0.7161(4) 0.4132(2) 0.0259(8) Uani 1 1 d . . . . .
C00D C 0.3295(3) 0.8209(3) 0.2554(2) 0.0209(7) Uani 1 1 d . . . . .
C00E C 0.4242(3) 0.7393(3) 0.2942(2) 0.0226(7) Uani 1 1 d . . . . .
H00E H 0.4736 0.6756 0.2594 0.027 Uiso 1 1 calc R U . . .
C00F C 0.5657(4) 0.3928(3) 0.3420(2) 0.0294(8) Uani 1 1 d . . . . .
C00G C -0.0693(3) 0.6174(4) 0.1351(2) 0.0244(7) Uani 1 1 d . . . . .
H00C H -0.1043 0.5234 0.1132 0.029 Uiso 1 1 calc R U . . .
H00D H -0.1415 0.6692 0.1064 0.029 Uiso 1 1 calc R U . . .
C00H C 0.3972(3) 0.7106(3) 0.1077(2) 0.0216(7) Uani 1 1 d . . . . .
H00H H 0.4984 0.7325 0.1002 0.026 Uiso 1 1 calc R U . . .
C00I C -0.1605(3) 0.7838(3) 0.3600(2) 0.0271(8) Uani 1 1 d . . . . .
H00I H -0.2206 0.8494 0.3841 0.032 Uiso 1 1 calc R U . . .
C00J C 0.5183(4) 0.3707(3) 0.1848(2) 0.0274(8) Uani 1 1 d . . . . .
H00J H 0.5549 0.3773 0.1332 0.033 Uiso 1 1 calc R U . . .
C00K C 0.0243(3) 0.5900(3) 0.2887(2) 0.0256(7) Uani 1 1 d . . . . .
H00K H 0.0871 0.5264 0.2651 0.031 Uiso 1 1 calc R U . . .
C00L C 0.4468(4) 0.7510(4) 0.3850(2) 0.0274(8) Uani 1 1 d . . . . .
H00L H 0.5115 0.6956 0.4102 0.033 Uiso 1 1 calc R U . . .
C00M C 0.4097(4) 0.3537(3) 0.3399(2) 0.0278(7) Uani 1 1 d . . . . .
H00M H 0.3733 0.3486 0.3918 0.033 Uiso 1 1 calc R U . . .
C00N C 0.1387(3) 0.7824(3) 0.1140(2) 0.0237(7) Uani 1 1 d . . . . .
H00F H 0.0747 0.8428 0.1459 0.028 Uiso 1 1 calc R U . . .
H00G H 0.1263 0.7944 0.0540 0.028 Uiso 1 1 calc R U . . .
C00O C 0.6179(4) 0.4004(3) 0.2647(3) 0.0295(8) Uani 1 1 d . . . . .
H00O H 0.7222 0.4260 0.2659 0.035 Uiso 1 1 calc R U . . .
C00P C 0.5349(4) 1.0005(3) 0.1715(2) 0.0275(8) Uani 1 1 d . . . . .
C00Q C 0.0238(3) 0.6198(4) 0.3784(2) 0.0267(7) Uani 1 1 d . . . . .
H00Q H 0.0851 0.5761 0.4149 0.032 Uiso 1 1 calc R U . . .
C00R C 0.3095(3) 0.8168(3) 0.1565(2) 0.0220(7) Uani 1 1 d . . . . .
C00S C 0.2735(4) 0.9247(4) 0.3994(3) 0.0314(8) Uani 1 1 d . . . . .
H00S H 0.2209 0.9857 0.4341 0.038 Uiso 1 1 calc R U . . .
C00T C 0.3735(4) 0.8445(4) 0.4377(2) 0.0301(8) Uani 1 1 d . . . . .
H00T H 0.3909 0.8538 0.4983 0.036 Uiso 1 1 calc R U . . .
C00U C 0.3640(4) 0.9557(3) 0.1410(2) 0.0268(7) Uani 1 1 d . . . . .
H00N H 0.3403 0.9535 0.0786 0.032 Uiso 1 1 calc R U . . .
H00P H 0.3040 1.0222 0.1709 0.032 Uiso 1 1 calc R U . . .
C00V C 0.2530(4) 0.9130(4) 0.3097(2) 0.0271(7) Uani 1 1 d . . . . .
H00V H 0.1868 0.9673 0.2846 0.033 Uiso 1 1 calc R U . . .
C00W C 0.6381(4) 0.9924(4) 0.1119(3) 0.0338(9) Uani 1 1 d . . . . .
H00W H 0.6014 0.9558 0.0529 0.041 Uiso 1 1 calc R U . . .
N00X N -0.0874(4) 0.7601(4) 0.5813(3) 0.0570(11) Uani 1 1 d . . . . .
C00Y C 0.5956(5) 1.0537(4) 0.2606(3) 0.0391(9) Uani 1 1 d . . . . .
H00Y H 0.5316 1.0605 0.3034 0.047 Uiso 1 1 calc R U . . .
C00Z C 0.6757(4) 0.4242(4) 0.4280(3) 0.0393(10) Uani 1 1 d . . . . .
H00R H 0.7743 0.3919 0.4189 0.059 Uiso 1 1 calc R U . . .
H00U H 0.6337 0.3814 0.4694 0.059 Uiso 1 1 calc R U . . .
H00$ H 0.6890 0.5193 0.4505 0.059 Uiso 1 1 calc R U . . .
C010 C 0.7562(5) 1.0968(4) 0.2838(3) 0.0517(13) Uani 1 1 d . . . . .
H010 H 0.7971 1.1316 0.3425 0.062 Uiso 1 1 calc R U . . .
C011 C 0.7931(4) 1.0365(4) 0.1369(3) 0.0445(11) Uani 1 1 d . . . . .
H011 H 0.8578 1.0304 0.0945 0.053 Uiso 1 1 calc R U . . .
C012 C 0.8528(5) 1.0883(4) 0.2217(4) 0.0481(12) Uani 1 1 d . . . . .
H012 H 0.9577 1.1178 0.2379 0.058 Uiso 1 1 calc R U . . .
C013 C -0.0766(4) 0.7412(4) 0.5047(3) 0.0415(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 O003 1.432(2) . ?
S001 O002 1.442(3) . ?
S001 N004 1.611(3) . ?
S001 C006 1.770(3) . ?
N004 C008 1.338(4) . ?
N005 C008 1.342(4) . ?
N005 C00N 1.467(4) . ?
N005 C00G 1.471(4) . ?
C006 C00A 1.384(5) . ?
C006 C00J 1.398(4) . ?
C007 C00K 1.391(4) . ?
C007 C00B 1.392(4) . ?
C007 C00G 1.517(4) . ?
C008 C009 1.473(4) . ?
C009 C00H 1.332(5) . ?
C009 H009 0.9300 . ?
C00A C00M 1.391(5) . ?
C00A H00A 0.9300 . ?
C00B C00I 1.405(5) . ?
C00B H00B 0.9300 . ?
C00C C00I 1.387(5) . ?
C00C C00Q 1.393(5) . ?
C00C C013 1.424(5) . ?
C00D C00E 1.380(4) . ?
C00D C00V 1.405(4) . ?
C00D C00R 1.536(4) . ?
C00E C00L 1.396(5) . ?
C00E H00E 0.9300 . ?
C00F C00O 1.376(5) . ?
C00F C00M 1.392(5) . ?
C00F C00Z 1.509(5) . ?
C00G H00C 0.9700 . ?
C00G H00D 0.9700 . ?
C00H C00R 1.511(4) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00J C00O 1.389(5) . ?
C00J H00J 0.9300 . ?
C00K C00Q 1.383(5) . ?
C00K H00K 0.9300 . ?
C00L C00T 1.383(5) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00N C00R 1.535(4) . ?
C00N H00F 0.9700 . ?
C00N H00G 0.9700 . ?
C00O H00O 0.9300 . ?
C00P C00W 1.387(5) . ?
C00P C00Y 1.410(5) . ?
C00P C00U 1.515(4) . ?
C00Q H00Q 0.9300 . ?
C00R C00U 1.554(4) . ?
C00S C00V 1.378(5) . ?
C00S C00T 1.393(5) . ?
C00S H00S 0.9300 . ?
C00T H00T 0.9300 . ?
C00U H00N 0.9700 . ?
C00U H00P 0.9700 . ?
C00V H00V 0.9300 . ?
C00W C011 1.377(5) . ?
C00W H00W 0.9300 . ?
N00X C013 1.201(5) . ?
C00Y C010 1.418(6) . ?
C00Y H00Y 0.9300 . ?
C00Z H00R 0.9600 . ?
C00Z H00U 0.9600 . ?
C00Z H00$ 0.9600 . ?
C010 C012 1.375(6) . ?
C010 H010 0.9300 . ?
C011 C012 1.347(7) . ?
C011 H011 0.9300 . ?
C012 H012 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
O003 S001 O002 116.62(15) . . ?
O003 S001 N004 105.77(14) . . ?
O002 S001 N004 113.58(14) . . ?
O003 S001 C006 108.13(15) . . ?
O002 S001 C006 107.31(14) . . ?
N004 S001 C006 104.70(14) . . ?
C008 N004 S001 122.3(2) . . ?
C008 N005 C00N 120.4(3) . . ?
C008 N005 C00G 121.8(3) . . ?
C00N N005 C00G 117.8(3) . . ?
C00A C006 C00J 120.5(3) . . ?
C00A C006 S001 119.2(2) . . ?
C00J C006 S001 120.2(3) . . ?
C00K C007 C00B 119.7(3) . . ?
C00K C007 C00G 120.1(3) . . ?
C00B C007 C00G 120.3(3) . . ?
N004 C008 N005 117.6(3) . . ?
N004 C008 C009 126.4(3) . . ?
N005 C008 C009 116.0(3) . . ?
C00H C009 C008 120.6(3) . . ?
C00H C009 H009 119.7 . . ?
C008 C009 H009 119.7 . . ?
C006 C00A C00M 119.5(3) . . ?
C006 C00A H00A 120.2 . . ?
C00M C00A H00A 120.2 . . ?
C007 C00B C00I 120.3(3) . . ?
C007 C00B H00B 119.9 . . ?
C00I C00B H00B 119.9 . . ?
C00I C00C C00Q 121.4(3) . . ?
C00I C00C C013 119.6(3) . . ?
C00Q C00C C013 118.9(3) . . ?
C00E C00D C00V 118.0(3) . . ?
C00E C00D C00R 122.3(3) . . ?
C00V C00D C00R 119.7(3) . . ?
C00D C00E C00L 120.8(3) . . ?
C00D C00E H00E 119.6 . . ?
C00L C00E H00E 119.6 . . ?
C00O C00F C00M 119.1(3) . . ?
C00O C00F C00Z 120.8(3) . . ?
C00M C00F C00Z 120.0(3) . . ?
N005 C00G C007 110.8(2) . . ?
N005 C00G H00C 109.5 . . ?
C007 C00G H00C 109.5 . . ?
N005 C00G H00D 109.5 . . ?
C007 C00G H00D 109.5 . . ?
H00C C00G H00D 108.1 . . ?
C009 C00H C00R 121.3(3) . . ?
C009 C00H H00H 119.4 . . ?
C00R C00H H00H 119.4 . . ?
C00C C00I C00B 118.7(3) . . ?
C00C C00I H00I 120.6 . . ?
C00B C00I H00I 120.6 . . ?
C00O C00J C006 118.7(3) . . ?
C00O C00J H00J 120.6 . . ?
C006 C00J H00J 120.6 . . ?
C00Q C00K C007 120.8(3) . . ?
C00Q C00K H00K 119.6 . . ?
C007 C00K H00K 119.6 . . ?
C00T C00L C00E 120.3(3) . . ?
C00T C00L H00L 119.8 . . ?
C00E C00L H00L 119.8 . . ?
C00A C00M C00F 120.6(3) . . ?
C00A C00M H00M 119.7 . . ?
C00F C00M H00M 119.7 . . ?
N005 C00N C00R 111.0(3) . . ?
N005 C00N H00F 109.4 . . ?
C00R C00N H00F 109.4 . . ?
N005 C00N H00G 109.4 . . ?
C00R C00N H00G 109.4 . . ?
H00F C00N H00G 108.0 . . ?
C00F C00O C00J 121.5(3) . . ?
C00F C00O H00O 119.2 . . ?
C00J C00O H00O 119.2 . . ?
C00W C00P C00Y 117.2(3) . . ?
C00W C00P C00U 120.8(3) . . ?
C00Y C00P C00U 122.0(3) . . ?
C00K C00Q C00C 119.1(3) . . ?
C00K C00Q H00Q 120.4 . . ?
C00C C00Q H00Q 120.4 . . ?
C00H C00R C00N 105.5(3) . . ?
C00H C00R C00D 112.8(3) . . ?
C00N C00R C00D 111.0(2) . . ?
C00H C00R C00U 109.4(3) . . ?
C00N C00R C00U 108.2(3) . . ?
C00D C00R C00U 109.9(3) . . ?
C00V C00S C00T 119.5(3) . . ?
C00V C00S H00S 120.2 . . ?
C00T C00S H00S 120.2 . . ?
C00L C00T C00S 119.6(3) . . ?
C00L C00T H00T 120.2 . . ?
C00S C00T H00T 120.2 . . ?
C00P C00U C00R 115.5(3) . . ?
C00P C00U H00N 108.4 . . ?
C00R C00U H00N 108.4 . . ?
C00P C00U H00P 108.4 . . ?
C00R C00U H00P 108.4 . . ?
H00N C00U H00P 107.5 . . ?
C00S C00V C00D 121.6(3) . . ?
C00S C00V H00V 119.2 . . ?
C00D C00V H00V 119.2 . . ?
C011 C00W C00P 122.3(4) . . ?
C011 C00W H00W 118.9 . . ?
C00P C00W H00W 118.9 . . ?
C00P C00Y C010 118.7(4) . . ?
C00P C00Y H00Y 120.7 . . ?
C010 C00Y H00Y 120.7 . . ?
C00F C00Z H00R 109.5 . . ?
C00F C00Z H00U 109.5 . . ?
H00R C00Z H00U 109.5 . . ?
C00F C00Z H00$ 109.5 . . ?
H00R C00Z H00$ 109.5 . . ?
H00U C00Z H00$ 109.5 . . ?
C012 C010 C00Y 121.7(4) . . ?
C012 C010 H010 119.2 . . ?
C00Y C010 H010 119.2 . . ?
C012 C011 C00W 121.3(4) . . ?
C012 C011 H011 119.4 . . ?
C00W C011 H011 119.4 . . ?
C011 C012 C010 118.9(4) . . ?
C011 C012 H012 120.6 . . ?
C010 C012 H012 120.6 . . ?
N00X C013 C00C 177.7(4) . . ?

_refine_diff_density_max         1.444
_refine_diff_density_min         -1.201
_refine_diff_density_rms         0.122

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_11a
_database_code_depnum_ccdc_archive 'CCDC 1525177'
_audit_update_record             
;
2017-01-02 deposited with the CCDC.
2017-05-09 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 H26 N2 O2 S'
_chemical_formula_weight         430.55

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   27.148(6)
_cell_length_b                   6.2305(14)
_cell_length_c                   27.401(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.154(5)
_cell_angle_gamma                90
_cell_volume                     4631.5(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2433
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      20.55

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_F_000             1824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.164
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36973
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_av_R_equivalents  0.1147
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.487
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4739
_reflns_number_gt                2576
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4739
_refine_ls_number_parameters     281
_refine_ls_number_restraints     77
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1764
_refine_ls_wR_factor_gt          0.1315
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_restrained_S_all      0.934
_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
S001 S 0.33332(3) 0.57669(12) 0.04892(3) 0.0580(3) Uani 1 1 d . U . . .
N2 N 0.33845(7) 0.9760(3) 0.15306(7) 0.0418(5) Uani 1 1 d . U . . .
O1 O 0.34291(9) 0.7099(4) 0.00834(7) 0.0768(7) Uani 1 1 d . U . . .
N3 N 0.32093(8) 0.7142(3) 0.09738(7) 0.0481(6) Uani 1 1 d . U . . .
C25 C 0.40029(9) 0.9045(4) 0.09329(9) 0.0401(6) Uani 1 1 d . U . . .
H25 H 0.4025 1.0103 0.0695 0.048 Uiso 1 1 calc R U . . .
C16 C 0.44129(9) 0.7973(4) 0.10727(9) 0.0403(6) Uani 1 1 d . U . . .
C007 C 0.35152(9) 0.8617(4) 0.11406(8) 0.0386(6) Uani 1 1 d . U . . .
C17 C 0.48807(9) 0.8368(4) 0.08227(9) 0.0406(6) Uani 1 1 d . U . . .
O2 O 0.36880(11) 0.4118(4) 0.05974(9) 0.0948(9) Uani 1 1 d . U . . .
C7 C 0.29182(9) 0.9314(4) 0.17706(9) 0.0461(6) Uani 1 1 d . U . . .
H7A H 0.2968 0.9533 0.2119 0.055 Uiso 1 1 calc R U . . .
H7B H 0.2832 0.7818 0.1719 0.055 Uiso 1 1 calc R U . . .
C9 C 0.37840(10) 1.1970(4) 0.21966(9) 0.0460(6) Uani 1 1 d . U . . .
C6 C 0.24947(9) 1.0698(4) 0.15878(9) 0.0467(7) Uani 1 1 d . U . . .
C8 C 0.36312(10) 1.1787(4) 0.16647(9) 0.0474(7) Uani 1 1 d . U . . .
H8A H 0.3411 1.2966 0.1580 0.057 Uiso 1 1 calc R U . . .
H8B H 0.3922 1.1939 0.1472 0.057 Uiso 1 1 calc R U . . .
C15 C 0.44067(11) 0.6396(4) 0.14689(10) 0.0507(7) Uani 1 1 d . U . . .
H15 H 0.4099 0.5966 0.1572 0.061 Uiso 1 1 calc R U . . .
C18 C 0.50775(10) 1.0399(4) 0.07895(10) 0.0523(7) Uani 1 1 d . U . . .
H18 H 0.4920 1.1550 0.0933 0.063 Uiso 1 1 calc R U . . .
C5 C 0.22044(10) 1.0125(5) 0.11811(10) 0.0564(7) Uani 1 1 d . U . . .
H5 H 0.2266 0.8846 0.1019 0.068 Uiso 1 1 calc R U . . .
C19 C 0.55053(11) 1.0744(5) 0.05458(11) 0.0591(8) Uani 1 1 d . U . . .
H19 H 0.5633 1.2126 0.0527 0.071 Uiso 1 1 calc R U . . .
C22 C 0.51247(11) 0.6698(4) 0.05962(11) 0.0558(7) Uani 1 1 d . U . . .
H22 H 0.4997 0.5315 0.0609 0.067 Uiso 1 1 calc R U . . .
C20 C 0.57447(11) 0.9080(5) 0.03311(10) 0.0572(8) Uani 1 1 d . U . . .
H20 H 0.6036 0.9320 0.0171 0.069 Uiso 1 1 calc R U . . .
C14 C 0.36494(11) 1.3764(5) 0.24563(10) 0.0568(8) Uani 1 1 d . U . . .
H14 H 0.3451 1.4801 0.2304 0.068 Uiso 1 1 calc R U . . .
C1 C 0.23868(11) 1.2598(5) 0.18245(11) 0.0624(8) Uani 1 1 d . U . . .
H1 H 0.2572 1.2992 0.2102 0.075 Uiso 1 1 calc R U . . .
C21 C 0.55504(11) 0.7061(5) 0.03549(11) 0.0634(8) Uani 1 1 d . U . . .
H21 H 0.5708 0.5923 0.0206 0.076 Uiso 1 1 calc R U . . .
C4 C 0.18242(12) 1.1447(6) 0.10150(11) 0.0687(9) Uani 1 1 d . U . . .
H4 H 0.1632 1.1050 0.0742 0.082 Uiso 1 1 calc R U . . .
C26 C 0.47934(12) 0.5537(5) 0.16917(12) 0.0710(9) Uani 1 1 d . U . . .
H26A H 0.5108 0.5918 0.1601 0.085 Uiso 1 1 calc R U . . .
H26B H 0.4753 0.4544 0.1941 0.085 Uiso 1 1 calc R U . . .
C10 C 0.40737(12) 1.0455(5) 0.24317(12) 0.0708(9) Uani 1 1 d . U . . .
H10 H 0.4169 0.9234 0.2264 0.085 Uiso 1 1 calc R U . . .
C3 C 0.17289(12) 1.3334(6) 0.12497(13) 0.0750(9) Uani 1 1 d . U . . .
H3 H 0.1475 1.4219 0.1134 0.090 Uiso 1 1 calc R U . . .
C13 C 0.38043(14) 1.4040(6) 0.29353(12) 0.0773(10) Uani 1 1 d . U . . .
H13 H 0.3715 1.5266 0.3104 0.093 Uiso 1 1 calc R U . . .
C12 C 0.40899(15) 1.2508(7) 0.31624(13) 0.0835(11) Uani 1 1 d . U . . .
H12 H 0.4192 1.2686 0.3488 0.100 Uiso 1 1 calc R U . . .
C2 C 0.20071(13) 1.3920(5) 0.16540(13) 0.0743(10) Uani 1 1 d . U . . .
H2 H 0.1942 1.5199 0.1814 0.089 Uiso 1 1 calc R U . . .
C11 C 0.42256(15) 1.0728(6) 0.29163(14) 0.0878(12) Uani 1 1 d . U . . .
H11 H 0.4421 0.9691 0.3073 0.105 Uiso 1 1 calc R U . . .
C23 C 0.27552(17) 0.4598(7) 0.03823(14) 0.1179(17) Uani 1 1 d . U . . .
H23A H 0.2512 0.5703 0.0330 0.177 Uiso 1 1 calc R U . . .
H23B H 0.2672 0.3747 0.0660 0.177 Uiso 1 1 calc R U . . .
H23C H 0.2763 0.3699 0.0098 0.177 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
S001 O1 1.419(2) . ?
S001 O2 1.432(3) . ?
S001 N3 1.626(2) . ?
S001 C23 1.745(4) . ?
N2 C007 1.343(3) . ?
N2 C7 1.475(3) . ?
N2 C8 1.470(3) . ?
N3 C007 1.309(3) . ?
C25 C16 1.342(3) . ?
C25 C007 1.485(4) . ?
C16 C15 1.465(3) . ?
C16 C17 1.486(3) . ?
C17 C18 1.378(4) . ?
C17 C22 1.392(4) . ?
C7 C6 1.508(4) . ?
C9 C10 1.373(4) . ?
C9 C14 1.382(4) . ?
C9 C8 1.505(3) . ?
C6 C1 1.386(4) . ?
C6 C5 1.387(4) . ?
C15 C26 1.309(4) . ?
C18 C19 1.378(4) . ?
C5 C4 1.384(4) . ?
C19 C20 1.368(4) . ?
C22 C21 1.371(4) . ?
C20 C21 1.367(4) . ?
C14 C13 1.374(4) . ?
C1 C2 1.387(4) . ?
C4 C3 1.370(5) . ?
C10 C11 1.386(5) . ?
C3 C2 1.367(5) . ?
C13 C12 1.365(5) . ?
C12 C11 1.356(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S001 O2 116.11(16) . . ?
O1 S001 N3 112.42(13) . . ?
O2 S001 N3 111.55(13) . . ?
O1 S001 C23 107.63(19) . . ?
O2 S001 C23 109.2(2) . . ?
N3 S001 C23 98.32(16) . . ?
C007 N2 C7 120.8(2) . . ?
C007 N2 C8 121.6(2) . . ?
C7 N2 C8 116.2(2) . . ?
C007 N3 S001 120.46(19) . . ?
C16 C25 C007 122.9(2) . . ?
C25 C16 C15 120.9(2) . . ?
C25 C16 C17 120.0(2) . . ?
C15 C16 C17 119.1(2) . . ?
N3 C007 N2 117.8(2) . . ?
N3 C007 C25 123.7(2) . . ?
N2 C007 C25 118.4(2) . . ?
C18 C17 C22 117.7(3) . . ?
C18 C17 C16 121.5(2) . . ?
C22 C17 C16 120.7(2) . . ?
N2 C7 C6 113.6(2) . . ?
C10 C9 C14 118.2(3) . . ?
C10 C9 C8 122.3(3) . . ?
C14 C9 C8 119.4(2) . . ?
C1 C6 C5 118.2(3) . . ?
C1 C6 C7 120.3(2) . . ?
C5 C6 C7 121.5(2) . . ?
N2 C8 C9 114.4(2) . . ?
C26 C15 C16 126.1(3) . . ?
C17 C18 C19 120.7(3) . . ?
C4 C5 C6 120.4(3) . . ?
C20 C19 C18 120.9(3) . . ?
C21 C22 C17 121.0(3) . . ?
C21 C20 C19 119.1(3) . . ?
C9 C14 C13 121.1(3) . . ?
C6 C1 C2 121.1(3) . . ?
C20 C21 C22 120.6(3) . . ?
C5 C4 C3 120.5(3) . . ?
C9 C10 C11 120.6(3) . . ?
C2 C3 C4 120.1(3) . . ?
C12 C13 C14 119.7(3) . . ?
C13 C12 C11 120.4(3) . . ?
C3 C2 C1 119.7(3) . . ?
C12 C11 C10 120.0(4) . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.054

_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_28
_database_code_depnum_ccdc_archive 'CCDC 1525520'
_audit_update_record             
;
2017-01-04 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 N O S'
_chemical_formula_weight         192.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   9.0423(4)
_cell_length_b                   10.9846(5)
_cell_length_c                   11.4374(5)
_cell_angle_alpha                91.995(2)
_cell_angle_beta                 100.164(2)
_cell_angle_gamma                103.818(2)
_cell_volume                     1082.32(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    0(2)
_cell_measurement_reflns_used    5346
_cell_measurement_theta_min      3.94
_cell_measurement_theta_max      66.64

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.348
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      0(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8009
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.939
_diffrn_reflns_theta_max         66.670
_diffrn_reflns_theta_full        66.670
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             3743
_reflns_number_gt                3367
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3743
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.2017
_refine_ls_wR_factor_gt          0.1948
_refine_ls_goodness_of_fit_ref   1.689
_refine_ls_restrained_S_all      1.689
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.12064(6) 0.40306(5) 0.30855(5) 0.0296(2) Uani 1 1 d . . . . .
O002 O 0.0628(2) 0.39399(18) 0.41841(15) 0.0391(5) Uani 1 1 d . . . . .
O003 O 0.0488(2) 0.30087(16) 0.21819(15) 0.0396(5) Uani 1 1 d . . . . .
N004 N 0.5428(2) 0.39493(18) 0.38342(18) 0.0308(5) Uani 1 1 d . . . . .
N005 N 0.3067(2) 0.43424(19) 0.33025(17) 0.0312(5) Uani 1 1 d . . . . .
C006 C 0.0319(3) 0.6257(2) 0.3069(2) 0.0343(5) Uani 1 1 d . . . . .
H006 H 0.0075 0.6098 0.3832 0.041 Uiso 1 1 calc R U . . .
C007 C 0.0925(2) 0.5427(2) 0.2471(2) 0.0291(5) Uani 1 1 d . . . . .
C008 C 0.3891(3) 0.3567(2) 0.37322(19) 0.0291(5) Uani 1 1 d . . . . .
C009 C 0.3230(3) 0.2245(2) 0.4049(2) 0.0354(6) Uani 1 1 d . . . . .
H009 H 0.2205 0.2223 0.4274 0.043 Uiso 1 1 calc R U . . .
C00A C 0.4268(3) 0.1916(2) 0.5122(2) 0.0340(6) Uani 1 1 d . . . . .
C00B C 0.0431(3) 0.7586(2) 0.1420(2) 0.0386(6) Uani 1 1 d . . . . .
C00C C 0.3535(3) 0.1115(2) 0.5980(2) 0.0362(6) Uani 1 1 d . . . . .
C00D C 0.0076(3) 0.7323(3) 0.2533(2) 0.0395(6) Uani 1 1 d . . . . .
H00D H -0.0345 0.7891 0.2937 0.047 Uiso 1 1 calc R U . . .
C00E C 0.6502(3) 0.3257(2) 0.4437(2) 0.0379(6) Uani 1 1 d . . . . .
H00A H 0.7432 0.3866 0.4895 0.046 Uiso 1 1 calc R U . . .
H00B H 0.6842 0.2779 0.3830 0.046 Uiso 1 1 calc R U . . .
C00F C 0.5797(3) 0.2370(2) 0.5259(2) 0.0372(6) Uani 1 1 d . . . . .
H00F H 0.6456 0.2121 0.5898 0.045 Uiso 1 1 calc R U . . .
C00G C 0.1289(3) 0.5663(3) 0.1359(2) 0.0381(6) Uani 1 1 d . . . . .
H00G H 0.1708 0.5094 0.0955 0.046 Uiso 1 1 calc R U . . .
C00H C 0.1038(3) 0.6731(3) 0.0844(2) 0.0427(6) Uani 1 1 d . . . . .
H00H H 0.1284 0.6888 0.0080 0.051 Uiso 1 1 calc R U . . .
C00I C 0.6121(3) 0.5127(2) 0.3342(2) 0.0369(6) Uani 1 1 d . . . . .
H00C H 0.7245 0.5373 0.3684 0.044 Uiso 1 1 calc R U . . .
H00E H 0.5663 0.5794 0.3613 0.044 Uiso 1 1 calc R U . . .
C00J C 0.4165(4) 0.1320(3) 0.7205(3) 0.0498(7) Uani 1 1 d . . . . .
H00J H 0.5063 0.1983 0.7484 0.060 Uiso 1 1 calc R U . . .
C00K C 0.2213(3) 0.0130(3) 0.5619(3) 0.0460(7) Uani 1 1 d . . . . .
H00K H 0.1744 -0.0021 0.4798 0.055 Uiso 1 1 calc R U . . .
C00L C 0.2204(4) -0.0417(3) 0.7620(3) 0.0548(8) Uani 1 1 d . . . . .
H00L H 0.1755 -0.0943 0.8172 0.066 Uiso 1 1 calc R U . . .
C00M C 0.1576(3) -0.0627(3) 0.6429(3) 0.0523(8) Uani 1 1 d . . . . .
H00M H 0.0690 -0.1304 0.6159 0.063 Uiso 1 1 calc R U . . .
C00N C 0.5921(4) 0.5084(3) 0.2000(3) 0.0566(8) Uani 1 1 d . . . . .
H00I H 0.6407 0.5929 0.1779 0.068 Uiso 1 1 calc R U . . .
H00N H 0.4798 0.4902 0.1661 0.068 Uiso 1 1 calc R U . . .
C00O C 0.0172(4) 0.8733(3) 0.0822(3) 0.0575(8) Uani 1 1 d . . . . .
H00O H -0.0458 0.9134 0.1250 0.086 Uiso 1 1 calc R U . . .
H00P H -0.0369 0.8489 -0.0004 0.086 Uiso 1 1 calc R U . . .
H00Q H 0.1174 0.9326 0.0831 0.086 Uiso 1 1 calc R U . . .
C00P C 0.3490(4) 0.0563(3) 0.8011(3) 0.0573(8) Uani 1 1 d . . . . .
H00R H 0.3918 0.0721 0.8839 0.069 Uiso 1 1 calc R U . . .
C00Q C 0.2928(4) 0.1313(3) 0.2926(3) 0.0561(8) Uani 1 1 d . . . . .
H00S H 0.3081 0.0496 0.3190 0.067 Uiso 1 1 calc R U . . .
H00T H 0.1828 0.1174 0.2531 0.067 Uiso 1 1 calc R U . . .
C00R C 0.6593(4) 0.4129(5) 0.1418(4) 0.0830(14) Uani 1 1 d . . . . .
H00U H 0.7311 0.3846 0.2046 0.100 Uiso 1 1 calc R U . . .
H00V H 0.7218 0.4561 0.0856 0.100 Uiso 1 1 calc R U . . .
C00S C 0.5421(5) 0.2953(4) 0.0739(4) 0.0781(12) Uani 1 1 d . . . . .
H00W H 0.4888 0.3208 -0.0010 0.094 Uiso 1 1 calc R U . . .
H00$ H 0.6005 0.2353 0.0517 0.094 Uiso 1 1 calc R U . . .
C00T C 0.4262(8) 0.2308(4) 0.1369(4) 0.109(2) Uani 1 1 d . . . . .
H00$ H 0.3342 0.2511 0.0983 0.131 Uiso 1 1 calc R U . . .
C00U C 0.3860(8) 0.1688(5) 0.2077(6) 0.153(3) Uani 1 1 d . . . . .
H00$ H 0.4493 0.1108 0.2124 0.183 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 O003 1.4436(18) . ?
S1 O002 1.4418(17) . ?
S1 N005 1.6063(19) . ?
S1 C007 1.763(2) . ?
N004 C008 1.335(3) . ?
N004 C00E 1.466(3) . ?
N004 C00I 1.473(3) . ?
N005 C008 1.314(3) . ?
C006 C00D 1.386(4) . ?
C006 C007 1.387(3) . ?
C006 H006 0.9500 . ?
C007 C00G 1.387(3) . ?
C008 C009 1.515(3) . ?
C009 C00A 1.518(3) . ?
C009 C00Q 1.558(4) . ?
C009 H009 1.0000 . ?
C00A C00F 1.332(4) . ?
C00A C00C 1.479(3) . ?
C00B C00D 1.390(4) . ?
C00B C00H 1.396(4) . ?
C00B C00O 1.502(4) . ?
C00C C00J 1.404(4) . ?
C00C C00K 1.396(4) . ?
C00D H00D 0.9500 . ?
C00E C00F 1.490(4) . ?
C00E H00A 0.9900 . ?
C00E H00B 0.9900 . ?
C00F H00F 0.9500 . ?
C00G C00H 1.379(4) . ?
C00G H00G 0.9500 . ?
C00H H00H 0.9500 . ?
C00I C00N 1.512(4) . ?
C00I H00C 0.9900 . ?
C00I H00E 0.9900 . ?
C00J C00P 1.387(4) . ?
C00J H00J 0.9500 . ?
C00K C00M 1.377(4) . ?
C00K H00K 0.9500 . ?
C00L C00M 1.368(5) . ?
C00L C00P 1.377(5) . ?
C00L H00L 0.9500 . ?
C00M H00M 0.9500 . ?
C00N C00R 1.520(6) . ?
C00N H00I 0.9900 . ?
C00N H00N 0.9900 . ?
C00O H00O 0.9800 . ?
C00O H00P 0.9800 . ?
C00O H00Q 0.9800 . ?
C00P H00R 0.9500 . ?
C00Q C00U 1.404(6) . ?
C00Q H00S 0.9900 . ?
C00Q H00T 0.9900 . ?
C00R C00S 1.543(5) . ?
C00R H00U 0.9900 . ?
C00R H00V 0.9900 . ?
C00S C00T 1.438(7) . ?
C00S H00W 0.9900 . ?
C00S H00$ 0.9900 . ?
C00T C00U 1.129(7) . ?
C00T H00$ 0.9500 . ?
C00U H00$ 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
O003 S1 O002 115.87(11) . . ?
O003 S1 N005 112.11(11) . . ?
O002 S1 N005 112.44(10) . . ?
O003 S1 C007 107.37(11) . . ?
O002 S1 C007 108.20(11) . . ?
N005 S1 C007 99.31(10) . . ?
C008 N004 C00E 123.1(2) . . ?
C008 N004 C00I 120.0(2) . . ?
C00E N004 C00I 116.83(19) . . ?
C008 N005 S1 124.27(17) . . ?
C00D C006 C007 118.9(2) . . ?
C00D C006 H006 120.5 . . ?
C007 C006 H006 120.5 . . ?
C006 C007 C00G 120.6(2) . . ?
C006 C007 S1 121.10(18) . . ?
C00G C007 S1 118.31(18) . . ?
N005 C008 N004 117.3(2) . . ?
N005 C008 C009 125.1(2) . . ?
N004 C008 C009 117.5(2) . . ?
C008 C009 C00A 110.86(19) . . ?
C008 C009 C00Q 109.1(2) . . ?
C00A C009 C00Q 113.9(2) . . ?
C008 C009 H009 107.6 . . ?
C00A C009 H009 107.6 . . ?
C00Q C009 H009 107.6 . . ?
C00F C00A C00C 122.7(2) . . ?
C00F C00A C009 118.7(2) . . ?
C00C C00A C009 118.5(2) . . ?
C00D C00B C00H 117.8(2) . . ?
C00D C00B C00O 122.7(3) . . ?
C00H C00B C00O 119.6(3) . . ?
C00J C00C C00K 117.3(3) . . ?
C00J C00C C00A 120.5(2) . . ?
C00K C00C C00A 122.2(2) . . ?
C006 C00D C00B 121.8(2) . . ?
C006 C00D H00D 119.1 . . ?
C00B C00D H00D 119.1 . . ?
N004 C00E C00F 112.77(19) . . ?
N004 C00E H00A 109.0 . . ?
C00F C00E H00A 109.0 . . ?
N004 C00E H00B 109.0 . . ?
C00F C00E H00B 109.0 . . ?
H00A C00E H00B 107.8 . . ?
C00A C00F C00E 121.8(2) . . ?
C00A C00F H00F 119.1 . . ?
C00E C00F H00F 119.1 . . ?
C00H C00G C007 119.5(2) . . ?
C00H C00G H00G 120.3 . . ?
C007 C00G H00G 120.3 . . ?
C00G C00H C00B 121.4(2) . . ?
C00G C00H H00H 119.3 . . ?
C00B C00H H00H 119.3 . . ?
N004 C00I C00N 115.9(2) . . ?
N004 C00I H00C 108.3 . . ?
C00N C00I H00C 108.3 . . ?
N004 C00I H00E 108.3 . . ?
C00N C00I H00E 108.3 . . ?
H00C C00I H00E 107.4 . . ?
C00P C00J C00C 120.7(3) . . ?
C00P C00J H00J 119.6 . . ?
C00C C00J H00J 119.6 . . ?
C00M C00K C00C 121.2(3) . . ?
C00M C00K H00K 119.4 . . ?
C00C C00K H00K 119.4 . . ?
C00M C00L C00P 119.6(3) . . ?
C00M C00L H00L 120.2 . . ?
C00P C00L H00L 120.2 . . ?
C00L C00M C00K 120.8(3) . . ?
C00L C00M H00M 119.6 . . ?
C00K C00M H00M 119.6 . . ?
C00I C00N C00R 116.0(3) . . ?
C00I C00N H00I 108.3 . . ?
C00R C00N H00I 108.3 . . ?
C00I C00N H00N 108.3 . . ?
C00R C00N H00N 108.3 . . ?
H00I C00N H00N 107.4 . . ?
C00B C00O H00O 109.5 . . ?
C00B C00O H00P 109.5 . . ?
H00O C00O H00P 109.5 . . ?
C00B C00O H00Q 109.5 . . ?
H00O C00O H00Q 109.5 . . ?
H00P C00O H00Q 109.5 . . ?
C00J C00P C00L 120.4(3) . . ?
C00J C00P H00R 119.8 . . ?
C00L C00P H00R 119.8 . . ?
C00U C00Q C009 115.9(3) . . ?
C00U C00Q H00S 108.3 . . ?
C009 C00Q H00S 108.3 . . ?
C00U C00Q H00T 108.3 . . ?
C009 C00Q H00T 108.3 . . ?
H00S C00Q H00T 107.4 . . ?
C00N C00R C00S 116.6(3) . . ?
C00N C00R H00U 108.1 . . ?
C00S C00R H00U 108.1 . . ?
C00N C00R H00V 108.1 . . ?
C00S C00R H00V 108.1 . . ?
H00U C00R H00V 107.3 . . ?
C00T C00S C00R 115.8(3) . . ?
C00T C00S H00W 108.3 . . ?
C00R C00S H00W 108.3 . . ?
C00T C00S H00$ 108.3 . . ?
C00R C00S H00$ 108.3 . . ?
H00W C00S H00$ 107.4 . . ?
C00U C00T C00S 153.2(9) . . ?
C00U C00T H00$ 103.4 . . ?
C00S C00T H00$ 103.4 . . ?
C00T C00U C00Q 153.4(9) . . ?
C00T C00U H00$ 103.3 . . ?
C00Q C00U H00$ 103.3 . . ?

_refine_diff_density_max         0.879
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.062

