# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_cd214695
_database_code_depnum_ccdc_archive 'CCDC 1037619'
_audit_update_record             
;
2014-12-04 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 Br2 N2 S2'
_chemical_formula_weight         536.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   21.883(3)
_cell_length_b                   5.8646(8)
_cell_length_c                   17.600(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.120(3)
_cell_angle_gamma                90
_cell_volume                     2134.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1491
_cell_measurement_theta_min      4.899
_cell_measurement_theta_max      49.730

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.045
_exptl_absorpt_coefficient_mu    4.005
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5998
_exptl_absorpt_correction_T_max  0.7457
_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            5836
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.970
_diffrn_reflns_theta_max         25.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1987
_reflns_number_gt                1558
_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)+(0.0612P)²+4.1731P] 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         1987
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1252
_refine_ls_wR_factor_gt          0.1158
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
Br1 Br 0.08782(3) 0.83107(11) 0.15187(3) 0.0696(3) Uani 1 1 d . . . . .
S1 S 0.41624(5) 0.7830(2) 0.52820(7) 0.0431(3) Uani 1 1 d . . . . .
N1 N 0.30344(15) 1.0011(5) 0.48866(19) 0.0311(7) Uani 1 1 d . . . . .
C1 C 0.21124(19) 0.8321(6) 0.3858(2) 0.0303(8) Uani 1 1 d . . . . .
C2 C 0.16441(19) 0.8903(7) 0.3143(2) 0.0351(9) Uani 1 1 d . . . . .
H2 H 0.1420 1.0272 0.3095 0.042 Uiso 1 1 calc R U . . .
C3 C 0.1514(2) 0.7422(8) 0.2500(2) 0.0396(10) Uani 1 1 d . . . . .
C4 C 0.1835(2) 0.5391(8) 0.2549(2) 0.0429(10) Uani 1 1 d . . . . .
H4 H 0.1740 0.4417 0.2108 0.051 Uiso 1 1 calc R U . . .
C5 C 0.2305(2) 0.4820(7) 0.3266(2) 0.0372(9) Uani 1 1 d . . . . .
H5 H 0.2529 0.3452 0.3309 0.045 Uiso 1 1 calc R U . . .
C6 C 0.24433(19) 0.6273(6) 0.3921(2) 0.0311(8) Uani 1 1 d . . . . .
C7 C 0.29588(18) 0.5868(6) 0.4724(2) 0.0314(8) Uani 1 1 d . . . . .
H7 H 0.3257 0.4689 0.4664 0.038 Uiso 1 1 calc R U . . .
C8 C 0.33181(18) 0.8109(7) 0.4938(2) 0.0309(8) Uani 1 1 d . . . . .
C9 C 0.23197(18) 0.9860(6) 0.4584(2) 0.0294(8) Uani 1 1 d . . . . .
H9 H 0.2154 1.1389 0.4404 0.035 Uiso 1 1 calc R U . . .
C10 C 0.4429(2) 1.0699(8) 0.5601(3) 0.0455(11) Uani 1 1 d . . . . .
H10A H 0.4868 1.0890 0.5599 0.055 Uiso 1 1 calc R U . . .
H10B H 0.4157 1.1771 0.5218 0.055 Uiso 1 1 calc R U . . .
C11 C 0.4408(3) 1.1246(10) 0.6412(3) 0.0698(16) Uani 1 1 d . . . . .
H11A H 0.3975 1.1041 0.6422 0.105 Uiso 1 1 calc R U . . .
H11B H 0.4538 1.2800 0.6541 0.105 Uiso 1 1 calc R U . . .
H11C H 0.4696 1.0252 0.6800 0.105 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
Br1 C3 1.901(4) . ?
S1 C8 1.753(4) . ?
S1 C10 1.809(5) . ?
N1 C8 1.265(5) . ?
N1 C9 1.480(5) . ?
C1 C2 1.381(6) . ?
C1 C6 1.388(5) . ?
C1 C9 1.507(5) . ?
C2 C3 1.380(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(6) . ?
C4 C5 1.382(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.510(5) . ?
C7 C8 1.514(5) . ?
C7 C9 1.589(5) 7_566 ?
C7 H7 0.9800 . ?
C9 C7 1.589(5) 7_566 ?
C9 H9 0.9800 . ?
C10 C11 1.477(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
C8 S1 C10 102.5(2) . . ?
C8 N1 C9 114.1(3) . . ?
C2 C1 C6 119.9(3) . . ?
C2 C1 C9 123.5(3) . . ?
C6 C1 C9 116.5(3) . . ?
C3 C2 C1 119.0(4) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 122.1(4) . . ?
C4 C3 Br1 120.2(3) . . ?
C2 C3 Br1 117.7(3) . . ?
C3 C4 C5 118.7(4) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 120.4(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.0(4) . . ?
C5 C6 C7 125.1(4) . . ?
C1 C6 C7 114.9(3) . . ?
C6 C7 C8 105.3(3) . . ?
C6 C7 C9 113.8(3) . 7_566 ?
C8 C7 C9 109.9(3) . 7_566 ?
C6 C7 H7 109.2 . . ?
C8 C7 H7 109.2 . . ?
C9 C7 H7 109.2 7_566 . ?
N1 C8 C7 123.0(3) . . ?
N1 C8 S1 122.9(3) . . ?
C7 C8 S1 114.0(3) . . ?
N1 C9 C1 109.3(3) . . ?
N1 C9 C7 111.4(3) . 7_566 ?
C1 C9 C7 113.8(3) . 7_566 ?
N1 C9 H9 107.3 . . ?
C1 C9 H9 107.3 . . ?
C7 C9 H9 107.3 7_566 . ?
C11 C10 S1 113.2(4) . . ?
C11 C10 H10A 108.9 . . ?
S1 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
S1 C10 H10B 108.9 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
C6 C1 C2 C3 0.0(6) . . . . ?
C9 C1 C2 C3 176.6(4) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C1 C2 C3 Br1 -178.7(3) . . . . ?
C2 C3 C4 C5 0.0(6) . . . . ?
Br1 C3 C4 C5 178.6(3) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C4 C5 C6 C1 -0.4(6) . . . . ?
C4 C5 C6 C7 -177.9(4) . . . . ?
C2 C1 C6 C5 0.2(6) . . . . ?
C9 C1 C6 C5 -176.6(3) . . . . ?
C2 C1 C6 C7 178.0(3) . . . . ?
C9 C1 C6 C7 1.2(5) . . . . ?
C5 C6 C7 C8 133.5(4) . . . . ?
C1 C6 C7 C8 -44.1(4) . . . . ?
C5 C6 C7 C9 -106.1(4) . . . 7_566 ?
C1 C6 C7 C9 76.3(4) . . . 7_566 ?
C9 N1 C8 C7 -1.1(5) . . . . ?
C9 N1 C8 S1 -179.9(3) . . . . ?
C6 C7 C8 N1 47.3(5) . . . . ?
C9 C7 C8 N1 -75.6(5) 7_566 . . . ?
C6 C7 C8 S1 -133.8(3) . . . . ?
C9 C7 C8 S1 103.3(3) 7_566 . . . ?
C10 S1 C8 N1 6.0(4) . . . . ?
C10 S1 C8 C7 -172.8(3) . . . . ?
C8 N1 C9 C1 -46.1(4) . . . . ?
C8 N1 C9 C7 80.6(4) . . . 7_566 ?
C2 C1 C9 N1 -130.6(4) . . . . ?
C6 C1 C9 N1 46.1(4) . . . . ?
C2 C1 C9 C7 104.1(4) . . . 7_566 ?
C6 C1 C9 C7 -79.2(4) . . . 7_566 ?
C8 S1 C10 C11 81.4(4) . . . . ?

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 H9 N1 0.98 2.55 3.315(5) 134.5 7_576
C9 H9 N1 0.98 2.55 3.315(5) 134.5 7_576

_refine_diff_density_max         1.057
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.093

_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_dm15240_0m
_database_code_depnum_ccdc_archive 'CCDC 1057819'
_audit_update_record             
;
2015-04-03 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;
_audit_creation_date             2015-04-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H13 N S'
_chemical_formula_sum            'C12 H13 N S'
_chemical_formula_weight         203.29
_chemical_absolute_configuration rmad
_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'
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.9732(9)
_cell_length_b                   7.2898(11)
_cell_length_c                   11.9181(19)
_cell_angle_alpha                90
_cell_angle_beta                 100.646(3)
_cell_angle_gamma                90
_cell_volume                     510.02(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2309
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.48
_cell_measurement_theta_min      2.79
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.935
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0660 before and 0.0436 after correction.
The Ratio of minimum to maximum transmission is 0.8964.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5103
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.610
_diffrn_reflns_theta_min         1.739
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_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         0.829
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                2788
_reflns_number_total             3056
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 1159 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         3056
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.075
_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)+(0.0445P)²+0.0364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0913
_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:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C6(H6), C8(H8)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.93111(8) 0.40707(11) 0.90515(4) 0.02478(15) Uani 1 1 d . . . . .
N1 N 0.6133(3) 0.5053(2) 0.73704(17) 0.0210(4) Uani 1 1 d . . . . .
C1 C 0.5225(4) 0.5404(3) 0.6302(2) 0.0197(4) Uani 1 1 d . . . . .
H1 H 0.3731 0.5904 0.6150 0.024 Uiso 1 1 calc R . . . .
C2 C 0.6316(3) 0.5091(3) 0.53604(18) 0.0161(4) Uani 1 1 d . . . . .
C3 C 0.5282(4) 0.5499(3) 0.42180(19) 0.0190(4) Uani 1 1 d . . . . .
H3 H 0.3804 0.6028 0.4060 0.023 Uiso 1 1 calc R . . . .
C4 C 0.6407(4) 0.5133(3) 0.33454(19) 0.0202(4) Uani 1 1 d . . . . .
H4 H 0.5702 0.5419 0.2584 0.024 Uiso 1 1 calc R . . . .
C5 C 0.8610(3) 0.4334(3) 0.35536(18) 0.0184(4) Uani 1 1 d . . . . .
C6 C 0.9639(3) 0.3944(3) 0.46578(16) 0.0164(4) Uani 1 1 d . . . . .
H6 H 1.1117 0.3413 0.4801 0.020 Uiso 1 1 calc R . . . .
C7 C 0.8526(3) 0.4322(3) 0.55861(17) 0.0156(4) Uani 1 1 d . . . . .
C8 C 0.9516(3) 0.3957(4) 0.67361(16) 0.0173(4) Uani 1 1 d . . . . .
H8 H 1.1002 0.3446 0.6924 0.021 Uiso 1 1 calc R . . . .
C9 C 0.8296(3) 0.4352(3) 0.75803(18) 0.0183(4) Uani 1 1 d . . . . .
C10 C 1.2319(4) 0.3642(3) 0.91323(19) 0.0249(5) Uani 1 1 d . . . . .
H10A H 1.2552 0.2379 0.8870 0.030 Uiso 1 1 calc R . . . .
H10B H 1.2947 0.4511 0.8632 0.030 Uiso 1 1 calc R . . . .
C11 C 1.3534(4) 0.3880(5) 1.03597(19) 0.0301(5) Uani 1 1 d . . . . .
H11A H 1.3282 0.5127 1.0617 0.045 Uiso 1 1 calc GR . . . .
H11B H 1.5171 0.3674 1.0408 0.045 Uiso 1 1 calc GR . . . .
H11C H 1.2935 0.2992 1.0847 0.045 Uiso 1 1 calc GR . . . .
C12 C 0.9775(4) 0.3926(4) 0.25646(17) 0.0229(4) Uani 1 1 d . . . . .
H12A H 1.1241 0.3328 0.2846 0.034 Uiso 1 1 calc GR . . . .
H12B H 1.0030 0.5074 0.2179 0.034 Uiso 1 1 calc GR . . . .
H12C H 0.8812 0.3111 0.2025 0.034 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 C9 1.758(2) . ?
S1 C10 1.809(2) . ?
N1 C1 1.314(3) . ?
N1 C9 1.369(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.416(3) . ?
C2 C3 1.419(3) . ?
C2 C7 1.414(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.365(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.418(3) . ?
C5 C6 1.376(3) . ?
C5 C12 1.505(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.419(3) . ?
C7 C8 1.414(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.377(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.518(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 S1 C10 103.26(10) . . ?
C1 N1 C9 117.19(19) . . ?
N1 C1 H1 117.7 . . ?
N1 C1 C2 124.6(2) . . ?
C2 C1 H1 117.7 . . ?
C1 C2 C3 122.99(19) . . ?
C7 C2 C1 117.60(19) . . ?
C7 C2 C3 119.41(18) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.15(19) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.2(2) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C12 119.49(19) . . ?
C6 C5 C4 119.25(19) . . ?
C6 C5 C12 121.26(19) . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 120.98(19) . . ?
C7 C6 H6 119.5 . . ?
C2 C7 C6 118.97(18) . . ?
C8 C7 C2 117.89(18) . . ?
C8 C7 C6 123.14(18) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 119.05(18) . . ?
C9 C8 H8 120.5 . . ?
N1 C9 S1 111.45(15) . . ?
N1 C9 C8 123.60(19) . . ?
C8 C9 S1 124.94(15) . . ?
S1 C10 H10A 109.9 . . ?
S1 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C11 C10 S1 108.96(16) . . ?
C11 C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
N1 C1 C2 C3 -179.6(2) . . . . ?
N1 C1 C2 C7 0.9(3) . . . . ?
C1 N1 C9 S1 176.98(16) . . . . ?
C1 N1 C9 C8 -1.9(3) . . . . ?
C1 C2 C3 C4 -178.8(2) . . . . ?
C1 C2 C7 C6 178.3(2) . . . . ?
C1 C2 C7 C8 -1.4(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C2 C7 C8 C9 0.3(3) . . . . ?
C3 C2 C7 C6 -1.2(3) . . . . ?
C3 C2 C7 C8 179.1(2) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C3 C4 C5 C12 179.0(2) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C2 0.8(3) . . . . ?
C5 C6 C7 C8 -179.6(2) . . . . ?
C6 C7 C8 C9 -179.3(2) . . . . ?
C7 C2 C3 C4 0.6(3) . . . . ?
C7 C8 C9 S1 -177.33(18) . . . . ?
C7 C8 C9 N1 1.4(3) . . . . ?
C9 S1 C10 C11 164.85(19) . . . . ?
C9 N1 C1 C2 0.7(3) . . . . ?
C10 S1 C9 N1 -167.73(15) . . . . ?
C10 S1 C9 C8 11.1(2) . . . . ?
C12 C5 C6 C7 -179.6(2) . . . . ?

_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_dm15371_0m
_database_code_depnum_ccdc_archive 'CCDC 1400768'
_audit_update_record             
;
2015-05-14 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;
_audit_creation_date             2015-05-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H21 N O2 S2'
_chemical_formula_sum            'C23 H21 N O2 S2'
_chemical_formula_weight         407.53
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   32.732(2)
_cell_length_b                   9.3213(7)
_cell_length_c                   12.9047(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.3470(10)
_cell_angle_gamma                90
_cell_volume                     3934.0(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7320
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.577
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.931
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0599 before and 0.0370 after correction.
The Ratio of minimum to maximum transmission is 0.8866.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19513
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.602
_diffrn_reflns_theta_min         1.245
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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                5022
_reflns_number_total             6047
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         6047
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0609P)²+2.1976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1104
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C18(H18), C19(H19), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.18153(2) 0.12793(4) 0.49452(2) 0.02153(9) Uani 1 1 d . . . . .
S2 S 0.11023(2) -0.00778(3) 0.65022(2) 0.01729(8) Uani 1 1 d . . . . .
O1 O 0.12637(3) -0.10912(10) 0.57922(8) 0.0237(2) Uani 1 1 d . . . . .
O2 O 0.09639(3) -0.05755(11) 0.74777(7) 0.0246(2) Uani 1 1 d . . . . .
N1 N 0.14642(3) 0.11219(11) 0.67809(8) 0.0162(2) Uani 1 1 d . . . . .
C1 C 0.15755(4) 0.20977(14) 0.59802(9) 0.0167(2) Uani 1 1 d . . . . .
C2 C 0.15085(4) 0.35077(14) 0.61156(10) 0.0184(2) Uani 1 1 d . . . . .
H2 H 0.1591 0.4156 0.5618 0.022 Uiso 1 1 calc R . . . .
C3 C 0.13086(4) 0.40378(14) 0.70270(10) 0.0176(2) Uani 1 1 d . . . . .
C4 C 0.11425(4) 0.54192(15) 0.70728(11) 0.0220(3) Uani 1 1 d . . . . .
H4 H 0.1159 0.6032 0.6507 0.026 Uiso 1 1 calc R . . . .
C5 C 0.09539(4) 0.58786(15) 0.79569(12) 0.0254(3) Uani 1 1 d . . . . .
H5 H 0.0846 0.6800 0.7983 0.030 Uiso 1 1 calc R . . . .
C6 C 0.09262(4) 0.49709(15) 0.88023(12) 0.0249(3) Uani 1 1 d . . . . .
H6 H 0.0796 0.5279 0.9389 0.030 Uiso 1 1 calc R . . . .
C7 C 0.10936(4) 0.35969(15) 0.87728(11) 0.0213(3) Uani 1 1 d . . . . .
H7 H 0.1075 0.2988 0.9340 0.026 Uiso 1 1 calc R . . . .
C8 C 0.12879(4) 0.31406(13) 0.78956(10) 0.0168(2) Uani 1 1 d . . . . .
C9 C 0.15086(4) 0.17286(13) 0.78466(9) 0.0156(2) Uani 1 1 d . . . . .
H9 H 0.1385 0.1060 0.8329 0.019 Uiso 1 1 calc R . . . .
C10 C 0.19649(4) 0.18449(13) 0.81293(9) 0.0161(2) Uani 1 1 d . . . . .
C11 C 0.21333(4) 0.30560(15) 0.86097(10) 0.0217(3) Uani 1 1 d . . . . .
H11 H 0.1966 0.3830 0.8760 0.026 Uiso 1 1 calc R . . . .
C12 C 0.25506(4) 0.31179(17) 0.88674(11) 0.0255(3) Uani 1 1 d . . . . .
H12 H 0.2661 0.3936 0.9183 0.031 Uiso 1 1 calc R . . . .
C13 C 0.28006(4) 0.19776(18) 0.86577(11) 0.0266(3) Uani 1 1 d . . . . .
H13 H 0.3079 0.2024 0.8828 0.032 Uiso 1 1 calc R . . . .
C14 C 0.26346(4) 0.07578(18) 0.81914(11) 0.0276(3) Uani 1 1 d . . . . .
H14 H 0.2802 -0.0021 0.8056 0.033 Uiso 1 1 calc R . . . .
C15 C 0.22202(4) 0.06957(15) 0.79271(10) 0.0222(3) Uani 1 1 d . . . . .
H15 H 0.2112 -0.0124 0.7611 0.027 Uiso 1 1 calc R . . . .
C16 C 0.19704(5) 0.28158(18) 0.42191(12) 0.0309(3) Uani 1 1 d . . . . .
H16A H 0.1733 0.3335 0.3972 0.046 Uiso 1 1 calc GR . . . .
H16B H 0.2123 0.2506 0.3640 0.046 Uiso 1 1 calc GR . . . .
H16C H 0.2138 0.3427 0.4657 0.046 Uiso 1 1 calc GR . . . .
C17 C 0.07018(4) 0.08450(14) 0.58422(10) 0.0181(2) Uani 1 1 d . . . . .
C18 C 0.06469(4) 0.06749(15) 0.47786(10) 0.0221(3) Uani 1 1 d . . . . .
H18 H 0.0818 0.0073 0.4419 0.026 Uiso 1 1 calc R . . . .
C19 C 0.03333(4) 0.14152(16) 0.42588(11) 0.0241(3) Uani 1 1 d . . . . .
H19 H 0.0294 0.1300 0.3546 0.029 Uiso 1 1 calc R . . . .
C20 C 0.00767(4) 0.23238(16) 0.47810(11) 0.0242(3) Uani 1 1 d . . . . .
C21 C 0.01377(4) 0.24708(17) 0.58541(12) 0.0282(3) Uani 1 1 d . . . . .
H21 H -0.0033 0.3074 0.6215 0.034 Uiso 1 1 calc R . . . .
C22 C 0.04461(4) 0.17369(17) 0.63884(11) 0.0251(3) Uani 1 1 d . . . . .
H22 H 0.0482 0.1837 0.7103 0.030 Uiso 1 1 calc R . . . .
C23 C -0.02570(5) 0.3135(2) 0.41981(14) 0.0351(4) Uani 1 1 d . . . . .
H23A H -0.0213 0.3088 0.3468 0.053 Uiso 1 1 calc GR . . . .
H23B H -0.0254 0.4119 0.4418 0.053 Uiso 1 1 calc GR . . . .
H23C H -0.0517 0.2715 0.4336 0.053 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 C1 1.7515(13) . ?
S1 C16 1.7960(15) . ?
S2 O1 1.4320(10) . ?
S2 O2 1.4324(10) . ?
S2 N1 1.6579(11) . ?
S2 C17 1.7585(13) . ?
N1 C1 1.4347(15) . ?
N1 C9 1.4885(16) . ?
C1 C2 1.3450(18) . ?
C2 H2 0.9300 . ?
C2 C3 1.4554(18) . ?
C3 C4 1.4000(18) . ?
C3 C8 1.4024(17) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.3941(19) . ?
C7 H7 0.9300 . ?
C7 C8 1.3878(18) . ?
C8 C9 1.5039(17) . ?
C9 H9 0.9800 . ?
C9 C10 1.5265(17) . ?
C10 C11 1.3910(18) . ?
C10 C15 1.3898(18) . ?
C11 H11 0.9300 . ?
C11 C12 1.3936(19) . ?
C12 H12 0.9300 . ?
C12 C13 1.375(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.3865(19) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.3860(18) . ?
C17 C22 1.3918(18) . ?
C18 H18 0.9300 . ?
C18 C19 1.3868(19) . ?
C19 H19 0.9300 . ?
C19 C20 1.387(2) . ?
C20 C21 1.398(2) . ?
C20 C23 1.504(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.380(2) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C1 S1 C16 101.28(7) . . ?
O1 S2 O2 119.14(6) . . ?
O1 S2 N1 107.74(6) . . ?
O1 S2 C17 107.45(6) . . ?
O2 S2 N1 106.06(6) . . ?
O2 S2 C17 109.14(6) . . ?
N1 S2 C17 106.68(6) . . ?
C1 N1 S2 118.14(8) . . ?
C1 N1 C9 113.98(10) . . ?
C9 N1 S2 119.90(8) . . ?
N1 C1 S1 114.07(9) . . ?
C2 C1 S1 127.24(10) . . ?
C2 C1 N1 118.58(11) . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.18(12) . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 122.31(12) . . ?
C4 C3 C8 118.90(12) . . ?
C8 C3 C2 118.78(11) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.36(13) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.30(13) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.04(13) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.85(13) . . ?
C8 C7 H7 120.1 . . ?
C3 C8 C9 116.69(11) . . ?
C7 C8 C3 120.52(12) . . ?
C7 C8 C9 122.66(11) . . ?
N1 C9 C8 110.03(10) . . ?
N1 C9 H9 108.6 . . ?
N1 C9 C10 107.78(10) . . ?
C8 C9 H9 108.6 . . ?
C8 C9 C10 113.24(10) . . ?
C10 C9 H9 108.6 . . ?
C11 C10 C9 122.02(11) . . ?
C15 C10 C9 119.35(11) . . ?
C15 C10 C11 118.60(12) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.44(13) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.42(13) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.58(13) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.19(14) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 119.6 . . ?
C14 C15 C10 120.76(13) . . ?
C14 C15 H15 119.6 . . ?
S1 C16 H16A 109.5 . . ?
S1 C16 H16B 109.5 . . ?
S1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 S2 119.18(10) . . ?
C18 C17 C22 120.91(12) . . ?
C22 C17 S2 119.91(10) . . ?
C17 C18 H18 120.5 . . ?
C17 C18 C19 119.04(13) . . ?
C19 C18 H18 120.5 . . ?
C18 C19 H19 119.3 . . ?
C20 C19 C18 121.32(13) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C21 118.46(13) . . ?
C19 C20 C23 120.38(14) . . ?
C21 C20 C23 121.17(14) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 C20 121.21(13) . . ?
C22 C21 H21 119.4 . . ?
C17 C22 H22 120.5 . . ?
C21 C22 C17 119.06(13) . . ?
C21 C22 H22 120.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
S1 C1 C2 C3 -179.20(9) . . . . ?
S2 N1 C1 S1 -67.13(11) . . . . ?
S2 N1 C1 C2 116.28(12) . . . . ?
S2 N1 C9 C8 -96.24(11) . . . . ?
S2 N1 C9 C10 139.85(9) . . . . ?
S2 C17 C18 C19 -179.37(11) . . . . ?
S2 C17 C22 C21 178.92(12) . . . . ?
O1 S2 N1 C1 69.26(11) . . . . ?
O1 S2 N1 C9 -143.68(9) . . . . ?
O1 S2 C17 C18 -10.46(13) . . . . ?
O1 S2 C17 C22 169.81(11) . . . . ?
O2 S2 N1 C1 -162.13(9) . . . . ?
O2 S2 N1 C9 -15.07(11) . . . . ?
O2 S2 C17 C18 -140.95(11) . . . . ?
O2 S2 C17 C22 39.32(13) . . . . ?
N1 S2 C17 C18 104.86(11) . . . . ?
N1 S2 C17 C22 -74.87(12) . . . . ?
N1 C1 C2 C3 -3.10(18) . . . . ?
N1 C9 C10 C11 135.93(12) . . . . ?
N1 C9 C10 C15 -45.75(15) . . . . ?
C1 N1 C9 C8 52.11(13) . . . . ?
C1 N1 C9 C10 -71.81(12) . . . . ?
C1 C2 C3 C4 -163.47(13) . . . . ?
C1 C2 C3 C8 17.61(19) . . . . ?
C2 C3 C4 C5 179.86(13) . . . . ?
C2 C3 C8 C7 -178.85(12) . . . . ?
C2 C3 C8 C9 5.10(17) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C3 C8 C9 N1 -38.20(15) . . . . ?
C3 C8 C9 C10 82.48(13) . . . . ?
C4 C3 C8 C7 2.20(19) . . . . ?
C4 C3 C8 C9 -173.86(11) . . . . ?
C4 C5 C6 C7 1.0(2) . . . . ?
C5 C6 C7 C8 0.0(2) . . . . ?
C6 C7 C8 C3 -1.6(2) . . . . ?
C6 C7 C8 C9 174.22(12) . . . . ?
C7 C8 C9 N1 145.84(12) . . . . ?
C7 C8 C9 C10 -93.48(14) . . . . ?
C8 C3 C4 C5 -1.2(2) . . . . ?
C8 C9 C10 C11 13.98(16) . . . . ?
C8 C9 C10 C15 -167.69(11) . . . . ?
C9 N1 C1 S1 143.93(9) . . . . ?
C9 N1 C1 C2 -32.67(16) . . . . ?
C9 C10 C11 C12 179.25(12) . . . . ?
C9 C10 C15 C14 -178.85(12) . . . . ?
C10 C11 C12 C13 -0.5(2) . . . . ?
C11 C10 C15 C14 -0.5(2) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
C12 C13 C14 C15 0.8(2) . . . . ?
C13 C14 C15 C10 -0.4(2) . . . . ?
C15 C10 C11 C12 0.91(19) . . . . ?
C16 S1 C1 N1 -172.14(10) . . . . ?
C16 S1 C1 C2 4.10(14) . . . . ?
C17 S2 N1 C1 -45.87(11) . . . . ?
C17 S2 N1 C9 101.20(10) . . . . ?
C17 C18 C19 C20 0.4(2) . . . . ?
C18 C17 C22 C21 -0.8(2) . . . . ?
C18 C19 C20 C21 -0.7(2) . . . . ?
C18 C19 C20 C23 178.97(14) . . . . ?
C19 C20 C21 C22 0.2(2) . . . . ?
C20 C21 C22 C17 0.5(2) . . . . ?
C22 C17 C18 C19 0.4(2) . . . . ?
C23 C20 C21 C22 -179.42(15) . . . . ?

_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_cd15102
_database_code_depnum_ccdc_archive 'CCDC 1421028'
_audit_update_record             
;
2015-08-28 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H26 N2 O2 S'
_chemical_formula_weight         466.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   13.134(2)
_cell_length_b                   15.776(3)
_cell_length_c                   12.1965(19)
_cell_angle_alpha                90
_cell_angle_beta                 106.946(4)
_cell_angle_gamma                90
_cell_volume                     2417.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2011
_cell_measurement_theta_min      4.772
_cell_measurement_theta_max      42.790

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.163
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6532
_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            13728
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.072
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4499
_reflns_number_gt                3363
_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)+(0.0695P)²+0.6184P] 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         4499
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0659
_refine_ls_wR_factor_ref         0.1582
_refine_ls_wR_factor_gt          0.1457
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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 0.27885(5) 1.01119(4) 0.46219(6) 0.0428(2) Uani 1 1 d . . . . .
N1 N 0.24516(16) 0.94047(13) 0.35499(18) 0.0419(5) Uani 1 1 d . . . . .
N2 N 0.05587(17) 0.93288(14) 0.3164(2) 0.0513(6) Uani 1 1 d . . . . .
O1 O 0.19081(17) 1.01802(13) 0.50693(17) 0.0577(5) Uani 1 1 d . . . . .
O2 O 0.37929(16) 0.98459(12) 0.53524(16) 0.0552(5) Uani 1 1 d . . . . .
C1 C 0.1412(2) 0.95140(16) 0.2741(2) 0.0441(6) Uani 1 1 d . . . . .
C2 C 0.1337(2) 0.98120(19) 0.1704(3) 0.0527(7) Uani 1 1 d . . . . .
H2 H 0.0665 0.9866 0.1181 0.063 Uiso 1 1 calc R U . . .
C3 C 0.2251(3) 1.00559(19) 0.1354(3) 0.0555(8) Uani 1 1 d . . . . .
C4 C 0.2181(3) 1.0566(2) 0.0399(3) 0.0801(11) Uani 1 1 d . . . . .
H4 H 0.1519 1.0764 -0.0035 0.096 Uiso 1 1 calc R U . . .
C5 C 0.3066(4) 1.0777(3) 0.0093(4) 0.0999(14) Uani 1 1 d . . . . .
H5 H 0.3006 1.1119 -0.0544 0.120 Uiso 1 1 calc R U . . .
C6 C 0.4041(4) 1.0487(3) 0.0719(4) 0.0966(14) Uani 1 1 d . . . . .
H6 H 0.4641 1.0626 0.0498 0.116 Uiso 1 1 calc R U . . .
C7 C 0.4146(3) 0.9989(2) 0.1681(3) 0.0764(10) Uani 1 1 d . . . . .
H7 H 0.4815 0.9808 0.2118 0.092 Uiso 1 1 calc R U . . .
C8 C 0.3248(2) 0.97595(19) 0.1991(3) 0.0534(7) Uani 1 1 d . . . . .
C9 C 0.3319(2) 0.92022(18) 0.3010(2) 0.0482(7) Uani 1 1 d . . . . .
H9 H 0.4000 0.9326 0.3581 0.058 Uiso 1 1 calc R U . . .
C10 C 0.3291(2) 0.82561(19) 0.2776(3) 0.0510(7) Uani 1 1 d . . . . .
C11 C 0.2924(2) 0.7920(2) 0.1681(3) 0.0576(8) Uani 1 1 d . . . . .
H11 H 0.2726 0.8279 0.1049 0.069 Uiso 1 1 calc R U . . .
C12 C 0.2852(3) 0.7051(2) 0.1529(3) 0.0721(10) Uani 1 1 d . . . . .
H12 H 0.2601 0.6829 0.0792 0.087 Uiso 1 1 calc R U . . .
C13 C 0.3146(3) 0.6514(2) 0.2444(4) 0.0807(11) Uani 1 1 d . . . . .
H13 H 0.3090 0.5930 0.2331 0.097 Uiso 1 1 calc R U . . .
C14 C 0.3522(3) 0.6837(2) 0.3531(4) 0.0808(11) Uani 1 1 d . . . . .
H14 H 0.3725 0.6474 0.4158 0.097 Uiso 1 1 calc R U . . .
C15 C 0.3599(2) 0.7707(2) 0.3693(3) 0.0659(9) Uani 1 1 d . . . . .
H15 H 0.3862 0.7924 0.4431 0.079 Uiso 1 1 calc R U . . .
C16 C 0.05007(19) 0.85401(16) 0.3670(2) 0.0430(6) Uani 1 1 d . . . . .
C17 C 0.0922(2) 0.78224(18) 0.3320(3) 0.0539(7) Uani 1 1 d . . . . .
H17 H 0.1253 0.7862 0.2744 0.065 Uiso 1 1 calc R U . . .
C18 C 0.0854(3) 0.7051(2) 0.3816(3) 0.0703(10) Uani 1 1 d . . . . .
H18 H 0.1153 0.6574 0.3584 0.084 Uiso 1 1 calc R U . . .
C19 C 0.0357(3) 0.6978(2) 0.4639(4) 0.0816(11) Uani 1 1 d . . . . .
H19 H 0.0313 0.6454 0.4972 0.098 Uiso 1 1 calc R U . . .
C20 C -0.0079(3) 0.7679(3) 0.4977(3) 0.0799(11) Uani 1 1 d . . . . .
H20 H -0.0433 0.7626 0.5532 0.096 Uiso 1 1 calc R U . . .
C21 C -0.0006(2) 0.8454(2) 0.4519(3) 0.0623(8) Uani 1 1 d . . . . .
H21 H -0.0295 0.8927 0.4773 0.075 Uiso 1 1 calc R U . . .
C22 C -0.0372(2) 0.9857(2) 0.2845(3) 0.0701(9) Uani 1 1 d . . . . .
H22A H -0.0190 1.0401 0.2603 0.105 Uiso 1 1 calc R U . . .
H22B H -0.0641 0.9928 0.3492 0.105 Uiso 1 1 calc R U . . .
H22C H -0.0907 0.9596 0.2229 0.105 Uiso 1 1 calc R U . . .
C23 C 0.2958(2) 1.10781(16) 0.3975(2) 0.0410(6) Uani 1 1 d . . . . .
C24 C 0.3950(2) 1.13025(19) 0.3903(3) 0.0533(7) Uani 1 1 d . . . . .
H24 H 0.4545 1.0980 0.4267 0.064 Uiso 1 1 calc R U . . .
C25 C 0.4047(2) 1.2008(2) 0.3287(3) 0.0612(8) Uani 1 1 d . . . . .
H25 H 0.4716 1.2163 0.3241 0.073 Uiso 1 1 calc R U . . .
C26 C 0.3173(3) 1.2497(2) 0.2732(3) 0.0616(8) Uani 1 1 d . . . . .
C27 C 0.2191(3) 1.22651(19) 0.2844(3) 0.0612(8) Uani 1 1 d . . . . .
H27 H 0.1597 1.2594 0.2496 0.073 Uiso 1 1 calc R U . . .
C28 C 0.2075(2) 1.15631(17) 0.3456(3) 0.0515(7) Uani 1 1 d . . . . .
H28 H 0.1410 1.1415 0.3521 0.062 Uiso 1 1 calc R U . . .
C29 C 0.3286(4) 1.3248(3) 0.2012(4) 0.1039(14) Uani 1 1 d . . . . .
H29A H 0.3907 1.3177 0.1758 0.156 Uiso 1 1 calc R U . . .
H29B H 0.3355 1.3756 0.2461 0.156 Uiso 1 1 calc R U . . .
H29C H 0.2667 1.3289 0.1359 0.156 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 1.419(2) . ?
S1 O2 1.423(2) . ?
S1 N1 1.677(2) . ?
S1 C23 1.760(3) . ?
N1 C1 1.443(3) . ?
N1 C9 1.507(3) . ?
N2 C1 1.395(3) . ?
N2 C16 1.401(3) . ?
N2 C22 1.436(4) . ?
C1 C2 1.326(4) . ?
C2 C3 1.438(4) . ?
C2 H2 0.9300 . ?
C3 C8 1.395(4) . ?
C3 C4 1.397(4) . ?
C4 C5 1.362(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.365(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.387(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.503(4) . ?
C9 C10 1.518(4) . ?
C9 H9 0.9800 . ?
C10 C15 1.379(4) . ?
C10 C11 1.387(4) . ?
C11 C12 1.383(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.365(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.381(4) . ?
C16 C21 1.391(4) . ?
C17 C18 1.374(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.353(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.363(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.360(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.377(4) . ?
C23 C28 1.380(4) . ?
C24 C25 1.370(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.384(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.385(4) . ?
C26 C29 1.508(5) . ?
C27 C28 1.368(4) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 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 119.48(13) . . ?
O1 S1 N1 106.91(11) . . ?
O2 S1 N1 106.13(11) . . ?
O1 S1 C23 109.29(12) . . ?
O2 S1 C23 108.70(12) . . ?
N1 S1 C23 105.42(12) . . ?
C1 N1 C9 114.3(2) . . ?
C1 N1 S1 115.83(16) . . ?
C9 N1 S1 114.88(16) . . ?
C1 N2 C16 120.1(2) . . ?
C1 N2 C22 119.4(2) . . ?
C16 N2 C22 118.9(2) . . ?
C2 C1 N2 125.6(3) . . ?
C2 C1 N1 119.2(2) . . ?
N2 C1 N1 115.1(2) . . ?
C1 C2 C3 122.7(3) . . ?
C1 C2 H2 118.6 . . ?
C3 C2 H2 118.6 . . ?
C8 C3 C4 118.7(3) . . ?
C8 C3 C2 118.4(3) . . ?
C4 C3 C2 122.9(3) . . ?
C5 C4 C3 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.1(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C7 120.6(4) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C8 119.8(4) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C8 C3 119.8(3) . . ?
C7 C8 C9 121.7(3) . . ?
C3 C8 C9 118.6(3) . . ?
C8 C9 N1 111.4(2) . . ?
C8 C9 C10 115.3(2) . . ?
N1 C9 C10 108.1(2) . . ?
C8 C9 H9 107.2 . . ?
N1 C9 H9 107.2 . . ?
C10 C9 H9 107.2 . . ?
C15 C10 C11 118.6(3) . . ?
C15 C10 C9 118.7(3) . . ?
C11 C10 C9 122.6(3) . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 119.8(4) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 120.9(3) . . ?
C10 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C21 118.1(3) . . ?
C17 C16 N2 120.9(3) . . ?
C21 C16 N2 120.9(3) . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 120.7(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 119.4(3) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 121.3(3) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C16 120.0(3) . . ?
C20 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C28 120.8(3) . . ?
C24 C23 S1 119.8(2) . . ?
C28 C23 S1 119.1(2) . . ?
C25 C24 C23 119.0(3) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C24 C25 C26 121.7(3) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C25 C26 C27 117.9(3) . . ?
C25 C26 C29 121.0(3) . . ?
C27 C26 C29 121.1(3) . . ?
C28 C27 C26 121.5(3) . . ?
C28 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
C27 C28 C23 119.1(3) . . ?
C27 C28 H28 120.4 . . ?
C23 C28 H28 120.4 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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 47.0(2) . . . . ?
O2 S1 N1 C1 175.57(18) . . . . ?
C23 S1 N1 C1 -69.2(2) . . . . ?
O1 S1 N1 C9 -176.28(18) . . . . ?
O2 S1 N1 C9 -47.7(2) . . . . ?
C23 S1 N1 C9 67.5(2) . . . . ?
C16 N2 C1 C2 129.2(3) . . . . ?
C22 N2 C1 C2 -36.3(4) . . . . ?
C16 N2 C1 N1 -54.2(3) . . . . ?
C22 N2 C1 N1 140.3(3) . . . . ?
C9 N1 C1 C2 -30.4(3) . . . . ?
S1 N1 C1 C2 106.6(3) . . . . ?
C9 N1 C1 N2 152.8(2) . . . . ?
S1 N1 C1 N2 -70.2(3) . . . . ?
N2 C1 C2 C3 174.7(3) . . . . ?
N1 C1 C2 C3 -1.8(4) . . . . ?
C1 C2 C3 C8 18.0(4) . . . . ?
C1 C2 C3 C4 -162.9(3) . . . . ?
C8 C3 C4 C5 -0.4(5) . . . . ?
C2 C3 C4 C5 -179.5(3) . . . . ?
C3 C4 C5 C6 0.3(7) . . . . ?
C4 C5 C6 C7 -1.1(7) . . . . ?
C5 C6 C7 C8 2.0(6) . . . . ?
C6 C7 C8 C3 -2.1(5) . . . . ?
C6 C7 C8 C9 178.5(3) . . . . ?
C4 C3 C8 C7 1.3(5) . . . . ?
C2 C3 C8 C7 -179.5(3) . . . . ?
C4 C3 C8 C9 -179.2(3) . . . . ?
C2 C3 C8 C9 -0.1(4) . . . . ?
C7 C8 C9 N1 149.6(3) . . . . ?
C3 C8 C9 N1 -29.8(3) . . . . ?
C7 C8 C9 C10 -86.7(3) . . . . ?
C3 C8 C9 C10 93.9(3) . . . . ?
C1 N1 C9 C8 44.7(3) . . . . ?
S1 N1 C9 C8 -92.7(2) . . . . ?
C1 N1 C9 C10 -83.1(3) . . . . ?
S1 N1 C9 C10 139.5(2) . . . . ?
C8 C9 C10 C15 164.9(3) . . . . ?
N1 C9 C10 C15 -69.6(3) . . . . ?
C8 C9 C10 C11 -18.0(4) . . . . ?
N1 C9 C10 C11 107.4(3) . . . . ?
C15 C10 C11 C12 1.3(4) . . . . ?
C9 C10 C11 C12 -175.7(3) . . . . ?
C10 C11 C12 C13 -0.4(5) . . . . ?
C11 C12 C13 C14 -0.3(5) . . . . ?
C12 C13 C14 C15 0.2(6) . . . . ?
C11 C10 C15 C14 -1.5(5) . . . . ?
C9 C10 C15 C14 175.7(3) . . . . ?
C13 C14 C15 C10 0.7(5) . . . . ?
C1 N2 C16 C17 -30.7(4) . . . . ?
C22 N2 C16 C17 134.8(3) . . . . ?
C1 N2 C16 C21 150.9(3) . . . . ?
C22 N2 C16 C21 -43.5(4) . . . . ?
C21 C16 C17 C18 -1.1(4) . . . . ?
N2 C16 C17 C18 -179.6(3) . . . . ?
C16 C17 C18 C19 1.3(5) . . . . ?
C17 C18 C19 C20 -0.1(6) . . . . ?
C18 C19 C20 C21 -1.3(6) . . . . ?
C19 C20 C21 C16 1.4(6) . . . . ?
C17 C16 C21 C20 -0.2(5) . . . . ?
N2 C16 C21 C20 178.2(3) . . . . ?
O1 S1 C23 C24 153.4(2) . . . . ?
O2 S1 C23 C24 21.5(3) . . . . ?
N1 S1 C23 C24 -92.0(2) . . . . ?
O1 S1 C23 C28 -32.4(3) . . . . ?
O2 S1 C23 C28 -164.3(2) . . . . ?
N1 S1 C23 C28 82.2(2) . . . . ?
C28 C23 C24 C25 -1.3(4) . . . . ?
S1 C23 C24 C25 172.8(2) . . . . ?
C23 C24 C25 C26 -0.4(5) . . . . ?
C24 C25 C26 C27 1.9(5) . . . . ?
C24 C25 C26 C29 -177.1(3) . . . . ?
C25 C26 C27 C28 -1.8(5) . . . . ?
C29 C26 C27 C28 177.2(3) . . . . ?
C26 C27 C28 C23 0.3(5) . . . . ?
C24 C23 C28 C27 1.3(4) . . . . ?
S1 C23 C28 C27 -172.8(2) . . . . ?

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
C24 H24 O2 0.93 2.47 3.365(3) 162.4 3_676
C21 H21 O1 0.93 2.60 3.445(4) 151.7 3_576
C9 H9 O2 0.98 2.40 2.924(3) 112.9 .

_refine_diff_density_max         0.398
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-4



