# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_DP_547
_database_code_depnum_ccdc_archive 'CCDC 1409828'
_audit_update_record             
;
2015-07-01 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_date             2015-03-08T14:55:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20  H17  N1  O1  S1'
_chemical_formula_sum            'C20 H17 N O S'
_chemical_formula_weight         319.4

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.3601(8)
_cell_length_b                   6.1956(3)
_cell_length_c                   16.4686(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.141(2)
_cell_angle_gamma                90
_cell_volume                     1586.29(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       char
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14231
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.31
_diffrn_reflns_theta_max         25.717
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_reflns_number_total             2997
_reflns_number_gt                2587
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0473P)²+0.4068P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2997
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0972
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.19
_refine_diff_density_rms         0.028

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.70812(3) -0.03366(7) 0.44582(3) 0.05512(15) Uani 1 d . .
N1 N 0.85711(8) 0.0541(2) 0.61187(8) 0.0454(3) Uani 1 d . .
O1 O 0.93282(9) -0.1585(3) 0.71890(9) 0.0886(5) Uani 1 d . .
C1 C 0.84944(8) 0.2038(2) 0.54470(9) 0.0400(3) Uani 1 d . .
C6 C 0.78336(9) 0.1776(2) 0.46736(9) 0.0418(3) Uani 1 d . .
C9 C 0.72457(9) 0.1736(2) 0.63991(9) 0.0443(3) Uani 1 d . .
C2 C 0.90254(9) 0.3838(3) 0.55646(10) 0.0487(4) Uani 1 d . .
H2 H 0.9437 0.4075 0.6092 0.058 Uiso 1 calc . .
C5 C 0.77546(11) 0.3276(3) 0.40234(10) 0.0524(4) Uani 1 d . .
H5 H 0.7316 0.3124 0.3508 0.063 Uiso 1 calc . .
C18 C 0.76884(10) 0.3369(3) 0.69635(9) 0.0498(4) Uani 1 d . .
H18 H 0.8285 0.3315 0.7183 0.06 Uiso 1 calc . .
C8 C 0.77538(9) -0.0164(2) 0.62311(10) 0.0471(4) Uani 1 d . .
H8 H 0.7904 -0.106 0.6747 0.057 Uiso 1 calc . .
C10 C 0.63729(10) 0.1875(3) 0.60744(10) 0.0532(4) Uani 1 d . .
H10 H 0.6075 0.0816 0.5697 0.064 Uiso 1 calc . .
C17 C 0.72591(11) 0.5016(3) 0.71915(10) 0.0538(4) Uani 1 d . .
H17 H 0.7567 0.6054 0.7573 0.065 Uiso 1 calc . .
C19 C 0.93182(10) -0.0443(3) 0.65860(10) 0.0535(4) Uani 1 d . .
C11 C 0.59069(10) 0.3580(3) 0.62935(10) 0.0519(4) Uani 1 d . .
C7 C 0.72984(11) -0.1634(3) 0.54883(11) 0.0532(4) Uani 1 d . .
H7A H 0.6759 -0.2114 0.5557 0.064 Uiso 1 calc . .
H7B H 0.7652 -0.2901 0.5503 0.064 Uiso 1 calc . .
C16 C 0.63567(11) 0.5191(3) 0.68641(10) 0.0502(4) Uani 1 d . .
C20 C 1.01157(10) -0.0149(3) 0.63297(12) 0.0617(5) Uani 1 d . .
H20A H 1.0463 0.0974 0.6669 0.093 Uiso 1 calc . .
H20B H 0.9957 0.0241 0.5737 0.093 Uiso 1 calc . .
H20C H 1.0436 -0.1473 0.642 0.093 Uiso 1 calc . .
C3 C 0.89462(11) 0.5276(3) 0.49064(12) 0.0573(4) Uani 1 d . .
H3 H 0.9317 0.6448 0.4983 0.069 Uiso 1 calc . .
C4 C 0.83172(12) 0.4975(3) 0.41345(12) 0.0606(5) Uani 1 d . .
H4 H 0.8273 0.5927 0.3686 0.073 Uiso 1 calc . .
C15 C 0.58843(14) 0.6892(3) 0.70760(12) 0.0666(5) Uani 1 d . .
H15 H 0.6171 0.7951 0.7459 0.08 Uiso 1 calc . .
C12 C 0.50053(12) 0.3748(4) 0.59509(14) 0.0774(6) Uani 1 d . .
H12 H 0.4701 0.2696 0.5574 0.093 Uiso 1 calc . .
C14 C 0.50159(15) 0.6997(4) 0.67259(14) 0.0793(6) Uani 1 d . .
H14 H 0.4714 0.8137 0.6865 0.095 Uiso 1 calc . .
C13 C 0.45753(14) 0.5414(4) 0.61611(15) 0.0844(6) Uani 1 d . .
H13 H 0.3981 0.55 0.5926 0.101 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C6 1.7555(15) . ?
S1 C7 1.8098(17) . ?
N1 C19 1.368(2) . ?
N1 C1 1.4185(18) . ?
N1 C8 1.4722(18) . ?
O1 C19 1.215(2) . ?
C1 C2 1.390(2) . ?
C1 C6 1.400(2) . ?
C6 C5 1.393(2) . ?
C9 C10 1.363(2) . ?
C9 C18 1.412(2) . ?
C9 C8 1.515(2) . ?
C2 C3 1.377(2) . ?
C2 H2 0.93 . ?
C5 C4 1.372(2) . ?
C5 H5 0.93 . ?
C18 C17 1.356(2) . ?
C18 H18 0.93 . ?
C8 C7 1.521(2) . ?
C8 H8 0.98 . ?
C10 C11 1.414(2) . ?
C10 H10 0.93 . ?
C17 C16 1.409(2) . ?
C17 H17 0.93 . ?
C19 C20 1.502(2) . ?
C11 C12 1.409(2) . ?
C11 C16 1.411(2) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C16 C15 1.413(2) . ?
C20 H20A 0.96 . ?
C20 H20B 0.96 . ?
C20 H20C 0.96 . ?
C3 C4 1.377(3) . ?
C3 H3 0.93 . ?
C4 H4 0.93 . ?
C15 C14 1.358(3) . ?
C15 H15 0.93 . ?
C12 C13 1.354(3) . ?
C12 H12 0.93 . ?
C14 C13 1.389(3) . ?
C14 H14 0.93 . ?
C13 H13 0.93 . ?

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
C6 S1 C7 102.78(7) . . ?
C19 N1 C1 125.21(13) . . ?
C19 N1 C8 118.97(13) . . ?
C1 N1 C8 115.38(11) . . ?
C2 C1 C6 119.46(13) . . ?
C2 C1 N1 121.07(13) . . ?
C6 C1 N1 119.31(13) . . ?
C5 C6 C1 118.85(14) . . ?
C5 C6 S1 116.78(12) . . ?
C1 C6 S1 124.37(11) . . ?
C10 C9 C18 118.24(14) . . ?
C10 C9 C8 123.02(14) . . ?
C18 C9 C8 118.60(13) . . ?
C3 C2 C1 120.51(15) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C5 C6 120.75(16) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C17 C18 C9 121.18(15) . . ?
C17 C18 H18 119.4 . . ?
C9 C18 H18 119.4 . . ?
N1 C8 C9 111.35(12) . . ?
N1 C8 C7 108.25(12) . . ?
C9 C8 C7 116.93(13) . . ?
N1 C8 H8 106.6 . . ?
C9 C8 H8 106.6 . . ?
C7 C8 H8 106.6 . . ?
C9 C10 C11 121.97(15) . . ?
C9 C10 H10 119 . . ?
C11 C10 H10 119 . . ?
C18 C17 C16 121.53(15) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
O1 C19 N1 120.10(16) . . ?
O1 C19 C20 120.55(15) . . ?
N1 C19 C20 119.33(15) . . ?
C12 C11 C16 118.58(16) . . ?
C12 C11 C10 122.22(16) . . ?
C16 C11 C10 119.19(15) . . ?
C8 C7 S1 113.06(11) . . ?
C8 C7 H7A 109 . . ?
S1 C7 H7A 109 . . ?
C8 C7 H7B 109 . . ?
S1 C7 H7B 109 . . ?
H7A C7 H7B 107.8 . . ?
C17 C16 C11 117.87(15) . . ?
C17 C16 C15 123.44(16) . . ?
C11 C16 C15 118.69(16) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C4 C3 C2 119.95(16) . . ?
C4 C3 H3 120 . . ?
C2 C3 H3 120 . . ?
C5 C4 C3 120.30(15) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C14 C15 C16 120.74(19) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C15 C14 C13 120.42(19) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?



# END of CIF
####################################################################### 
# 
# 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_DP_548
_database_code_depnum_ccdc_archive 'CCDC 1409829'
_audit_update_record             
;
2015-07-01 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_date             2014-12-19T18:21:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17  H17  N1  O1  S1'
_chemical_formula_sum            'C17 H17 N O S'
_chemical_formula_weight         283.37
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_Int_Tables_number      33
loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   6.2101(4)
_cell_length_b                   21.6012(15)
_cell_length_c                   10.6587(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1429.82(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       char
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      301(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_number            16452
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.131
_diffrn_reflns_theta_max         25.053
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.98
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_number_total             2542
_reflns_number_gt                2113
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0433P)²+0.1081P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2542
_refine_ls_number_parameters     183
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0847
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 867 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.13
_refine_diff_density_rms         0.03

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.49186(17) 0.49167(4) 0.54363(12) 0.0619(3) Uani 1 d . .
N1 N 0.4454(4) 0.35840(12) 0.6541(2) 0.0377(6) Uani 1 d . .
O1 O 0.6832(4) 0.28209(11) 0.6955(2) 0.0590(7) Uani 1 d . .
C16 C 0.5484(6) 0.31811(15) 0.7338(3) 0.0411(8) Uani 1 d . .
C6 C 0.2876(5) 0.40284(13) 0.6934(3) 0.0364(7) Uani 1 d . .
C13 C 0.0294(5) 0.30831(15) 0.3547(3) 0.0418(8) Uani 1 d . .
H13 H -0.094 0.2856 0.3729 0.05 Uiso 1 calc . .
C10 C 0.3916(5) 0.37545(15) 0.3054(3) 0.0438(8) Uani 1 d . .
H10 H 0.5132 0.399 0.2873 0.053 Uiso 1 calc . .
C9 C 0.3595(5) 0.35525(13) 0.4262(3) 0.0346(7) Uani 1 d . .
C12 C 0.0647(5) 0.32776(14) 0.2331(3) 0.0398(8) Uani 1 d . .
C8 C 0.5296(5) 0.36443(14) 0.5263(3) 0.0398(7) Uani 1 d . .
H8 H 0.634 0.3308 0.5154 0.048 Uiso 1 calc . .
C5 C 0.1165(5) 0.38539(16) 0.7684(3) 0.0448(9) Uani 1 d . .
H5 H 0.0989 0.3439 0.7891 0.054 Uiso 1 calc . .
C11 C 0.2488(6) 0.36182(15) 0.2098(3) 0.0472(8) Uani 1 d . .
H11 H 0.2769 0.3757 0.1288 0.057 Uiso 1 calc . .
C14 C 0.1724(5) 0.32165(15) 0.4499(3) 0.0410(8) Uani 1 d . .
H14 H 0.1436 0.308 0.531 0.049 Uiso 1 calc . .
C1 C 0.3015(5) 0.46406(14) 0.6516(3) 0.0430(8) Uani 1 d . .
C4 C -0.0279(6) 0.42812(19) 0.8129(4) 0.0576(10) Uani 1 d . .
H4 H -0.137 0.4159 0.8673 0.069 Uiso 1 calc . .
C3 C -0.0111(6) 0.4889(2) 0.7772(4) 0.0605(12) Uani 1 d . .
H3 H -0.1065 0.5182 0.8087 0.073 Uiso 1 calc . .
C7 C 0.6568(5) 0.42451(17) 0.5179(3) 0.0531(10) Uani 1 d . .
H7A H 0.7228 0.4274 0.4356 0.064 Uiso 1 calc . .
H7B H 0.7713 0.4238 0.5798 0.064 Uiso 1 calc . .
C2 C 0.1472(6) 0.50597(16) 0.6948(4) 0.0577(11) Uani 1 d . .
H2 H 0.1521 0.5467 0.6667 0.069 Uiso 1 calc . .
C17 C 0.4964(6) 0.31977(19) 0.8716(3) 0.0540(10) Uani 1 d . .
H17A H 0.374 0.2939 0.8879 0.081 Uiso 1 calc . .
H17B H 0.4643 0.3615 0.8961 0.081 Uiso 1 calc . .
H17C H 0.6178 0.305 0.9186 0.081 Uiso 1 calc . .
C15 C -0.0904(7) 0.31187(18) 0.1287(4) 0.0585(10) Uani 1 d . .
H15A H -0.2334 0.3239 0.1525 0.088 Uiso 1 calc . .
H15B H -0.0869 0.2681 0.1135 0.088 Uiso 1 calc . .
H15C H -0.0493 0.3335 0.0537 0.088 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.754(4) . ?
S1 C7 1.797(4) . ?
N1 C16 1.375(4) . ?
N1 C6 1.434(4) . ?
N1 C8 1.465(5) . ?
O1 C16 1.214(4) . ?
C16 C17 1.504(5) . ?
C6 C5 1.382(4) . ?
C6 C1 1.398(4) . ?
C13 C14 1.379(5) . ?
C13 C12 1.380(5) . ?
C13 H13 0.93 . ?
C10 C9 1.375(5) . ?
C10 C11 1.383(5) . ?
C10 H10 0.93 . ?
C9 C14 1.393(4) . ?
C9 C8 1.515(4) . ?
C12 C11 1.382(5) . ?
C12 C15 1.512(5) . ?
C8 C7 1.522(4) . ?
C8 H8 0.98 . ?
C5 C4 1.371(5) . ?
C5 H5 0.93 . ?
C11 H11 0.93 . ?
C14 H14 0.93 . ?
C1 C2 1.396(5) . ?
C4 C3 1.370(6) . ?
C4 H4 0.93 . ?
C3 C2 1.370(6) . ?
C3 H3 0.93 . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C2 H2 0.93 . ?
C17 H17A 0.96 . ?
C17 H17B 0.96 . ?
C17 H17C 0.96 . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?

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 C7 102.12(15) . . ?
C16 N1 C6 124.1(3) . . ?
C16 N1 C8 117.7(3) . . ?
C6 N1 C8 117.1(2) . . ?
O1 C16 N1 121.3(3) . . ?
O1 C16 C17 119.4(3) . . ?
N1 C16 C17 119.3(3) . . ?
C5 C6 C1 119.3(3) . . ?
C5 C6 N1 120.8(3) . . ?
C1 C6 N1 119.9(3) . . ?
C14 C13 C12 121.7(3) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C9 C10 C11 122.0(3) . . ?
C9 C10 H10 119 . . ?
C11 C10 H10 119 . . ?
C10 C9 C14 117.2(3) . . ?
C10 C9 C8 121.1(3) . . ?
C14 C9 C8 121.5(3) . . ?
C13 C12 C11 117.5(3) . . ?
C13 C12 C15 121.4(3) . . ?
C11 C12 C15 121.0(3) . . ?
N1 C8 C9 113.2(2) . . ?
N1 C8 C7 108.4(3) . . ?
C9 C8 C7 115.6(3) . . ?
N1 C8 H8 106.3 . . ?
C9 C8 H8 106.3 . . ?
C7 C8 H8 106.3 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C14 C9 120.8(3) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C2 C1 C6 117.8(3) . . ?
C2 C1 S1 117.3(3) . . ?
C6 C1 S1 124.9(3) . . ?
C3 C4 C5 119.9(4) . . ?
C3 C4 H4 120 . . ?
C5 C4 H4 120 . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C8 C7 S1 112.5(2) . . ?
C8 C7 H7A 109.1 . . ?
S1 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
S1 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C3 C2 C1 121.9(3) . . ?
C3 C2 H2 119 . . ?
C1 C2 H2 119 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?



# END of CIF
####################################################################### 
# 
# 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_DP_521
_database_code_depnum_ccdc_archive 'CCDC 1409837'
_audit_update_record             
;
2015-07-01 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_date             2015-01-05T15:34:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16  H21  N1  O3  S1'
_chemical_formula_sum            'C16 H21 N O3 S'
_chemical_formula_weight         307.4
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_Int_Tables_number      33
loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   9.3777(6)
_cell_length_b                   9.5320(6)
_cell_length_c                   34.929(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3122.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       char
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_number            22493
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         1.166
_diffrn_reflns_theta_max         26.055
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_number_total             6161
_reflns_number_gt                5096
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0480P)²+0.6028P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6161
_refine_ls_number_parameters     383
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1055
_refine_ls_wR_factor_gt          0.0849
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 2113 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_diff_density_max         0.2
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.047

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.85152(10) 0.58430(11) 0.36286(3) 0.0238(3) Uani 1 d . .
S2 S 0.57389(10) 0.58746(12) 0.63790(3) 0.0249(3) Uani 1 d . .
O5 O 0.6379(3) 0.5355(3) 0.43193(9) 0.0228(7) Uani 1 d . .
O2 O 0.3703(3) 0.5480(3) 0.56701(9) 0.0268(7) Uani 1 d . .
O4 O 0.3962(3) 0.6745(3) 0.28577(9) 0.0284(7) Uani 1 d . .
O1 O 0.1202(3) 0.6809(3) 0.71603(9) 0.0273(7) Uani 1 d . .
O6 O 0.8034(4) 0.4128(3) 0.46412(11) 0.0432(9) Uani 1 d . .
N1 N 0.3536(3) 0.6561(3) 0.69947(11) 0.0205(8) Uani 1 d . .
H1 H 0.4338 0.6996 0.6982 0.025 Uiso 1 calc . .
N2 N 0.6304(4) 0.6504(3) 0.30151(10) 0.0200(8) Uani 1 d . .
H2 H 0.7098 0.695 0.3032 0.024 Uiso 1 calc . .
C24 C 0.4578(4) 0.6736(4) 0.56897(12) 0.0226(10) Uani 1 d . .
H24 H 0.5531 0.6522 0.5591 0.027 Uiso 1 calc . .
C15 C 0.6880(5) 0.4192(4) 0.44975(13) 0.0260(10) Uani 1 d . .
C31 C 0.2414(4) 0.7290(4) 0.71318(13) 0.0207(9) Uani 1 d . .
C2 C 0.6313(4) 0.5091(4) 0.31339(12) 0.0198(9) Uani 1 d . .
C7 C 0.5171(4) 0.7237(5) 0.28764(13) 0.0209(9) Uani 1 d . .
C23 C 0.4697(4) 0.7168(4) 0.61061(12) 0.0208(9) Uani 1 d . .
H23 H 0.3737 0.7225 0.6216 0.025 Uiso 1 calc . .
C25 C 0.3911(5) 0.7852(5) 0.54452(14) 0.0257(10) Uani 1 d . .
H25A H 0.2927 0.7984 0.5522 0.031 Uiso 1 calc . .
H25B H 0.3915 0.7549 0.518 0.031 Uiso 1 calc . .
C1 C 0.7266(4) 0.4665(4) 0.34209(12) 0.0205(9) Uani 1 d . .
O3 O 0.5270(5) 0.4449(4) 0.52843(14) 0.0792(16) Uani 1 d . .
C18 C 0.3521(4) 0.5155(4) 0.68696(12) 0.0194(9) Uani 1 d . .
C28 C 0.5420(5) 0.8590(4) 0.61468(13) 0.0240(10) Uani 1 d . .
H28A H 0.6417 0.8502 0.6077 0.029 Uiso 1 calc . .
H28B H 0.5373 0.8887 0.6412 0.029 Uiso 1 calc . .
C17 C 0.4459(4) 0.4718(5) 0.65780(12) 0.0222(10) Uani 1 d . .
C22 C 0.4472(5) 0.3320(4) 0.64682(14) 0.0288(11) Uani 1 d . .
H22 H 0.5098 0.3031 0.6278 0.035 Uiso 1 calc . .
C20 C 0.2646(5) 0.2781(5) 0.69196(15) 0.0327(12) Uani 1 d . .
H20 H 0.2038 0.2133 0.7034 0.039 Uiso 1 calc . .
C32 C 0.2755(5) 0.8762(4) 0.72582(14) 0.0270(10) Uani 1 d . .
H32A H 0.2051 0.9395 0.7159 0.04 Uiso 1 calc . .
H32B H 0.3679 0.9023 0.7164 0.04 Uiso 1 calc . .
H32C H 0.2753 0.8806 0.7533 0.04 Uiso 1 calc . .
C9 C 0.7417(4) 0.7083(4) 0.39011(12) 0.0189(9) Uani 1 d . .
H9 H 0.6471 0.7138 0.3783 0.023 Uiso 1 calc . .
C19 C 0.2609(5) 0.4176(4) 0.70369(14) 0.0253(10) Uani 1 d . .
H19 H 0.1976 0.4455 0.7227 0.03 Uiso 1 calc . .
C10 C 0.7252(4) 0.6604(4) 0.43171(12) 0.0203(9) Uani 1 d . .
H10 H 0.8193 0.6385 0.4423 0.024 Uiso 1 calc . .
C14 C 0.8126(5) 0.8527(4) 0.38797(13) 0.0235(10) Uani 1 d . .
H14A H 0.9113 0.8445 0.396 0.028 Uiso 1 calc . .
H14B H 0.8119 0.8849 0.3616 0.028 Uiso 1 calc . .
C13 C 0.7378(5) 0.9611(4) 0.41306(13) 0.0264(10) Uani 1 d . .
H13A H 0.7896 1.0492 0.412 0.032 Uiso 1 calc . .
H13B H 0.6423 0.9774 0.4034 0.032 Uiso 1 calc . .
C3 C 0.5418(5) 0.4104(4) 0.29666(14) 0.0249(10) Uani 1 d . .
H3 H 0.4772 0.4382 0.2779 0.03 Uiso 1 calc . .
C5 C 0.6436(5) 0.2281(5) 0.33550(15) 0.0313(11) Uani 1 d . .
H5 H 0.6478 0.1343 0.3428 0.038 Uiso 1 calc . .
C26 C 0.4700(5) 0.9237(4) 0.54783(14) 0.0293(11) Uani 1 d . .
H26A H 0.423 0.9941 0.5323 0.035 Uiso 1 calc . .
H26B H 0.5668 0.9129 0.5386 0.035 Uiso 1 calc . .
C27 C 0.4721(5) 0.9708(5) 0.58941(13) 0.0265(10) Uani 1 d . .
H27A H 0.3753 0.9875 0.5981 0.032 Uiso 1 calc . .
H27B H 0.5247 1.0581 0.5916 0.032 Uiso 1 calc . .
C8 C 0.5502(5) 0.8695(4) 0.27467(14) 0.0277(11) Uani 1 d . .
H8A H 0.5551 0.8717 0.2472 0.041 Uiso 1 calc . .
H8B H 0.6402 0.8984 0.2852 0.041 Uiso 1 calc . .
H8C H 0.4767 0.9321 0.2833 0.041 Uiso 1 calc . .
C6 C 0.7324(5) 0.3257(4) 0.35241(13) 0.0270(11) Uani 1 d . .
H6 H 0.7971 0.2967 0.371 0.032 Uiso 1 calc . .
C12 C 0.7298(5) 0.9108(4) 0.45442(13) 0.0274(11) Uani 1 d . .
H12A H 0.8254 0.9012 0.4647 0.033 Uiso 1 calc . .
H12B H 0.6792 0.9795 0.4698 0.033 Uiso 1 calc . .
C4 C 0.5481(5) 0.2712(5) 0.30767(15) 0.0304(11) Uani 1 d . .
H4 H 0.4877 0.2061 0.2963 0.037 Uiso 1 calc . .
C11 C 0.6531(5) 0.7705(5) 0.45650(15) 0.0251(10) Uani 1 d . .
H11A H 0.6515 0.7384 0.4829 0.03 Uiso 1 calc . .
H11B H 0.5552 0.7824 0.4481 0.03 Uiso 1 calc . .
C29 C 0.4169(6) 0.4418(5) 0.54532(16) 0.0365(12) Uani 1 d . .
C21 C 0.3574(5) 0.2345(5) 0.66358(15) 0.0337(12) Uani 1 d . .
H21 H 0.3595 0.1411 0.6559 0.04 Uiso 1 calc . .
C16 C 0.5812(5) 0.3036(5) 0.44763(16) 0.0369(12) Uani 1 d . .
H16A H 0.6212 0.2198 0.4585 0.055 Uiso 1 calc . .
H16B H 0.5564 0.2868 0.4214 0.055 Uiso 1 calc . .
H16C H 0.4973 0.3297 0.4617 0.055 Uiso 1 calc . .
C30 C 0.3124(6) 0.3213(5) 0.54531(17) 0.0420(13) Uani 1 d . .
H30A H 0.336 0.2574 0.525 0.063 Uiso 1 calc . .
H30B H 0.2177 0.3568 0.5414 0.063 Uiso 1 calc . .
H30C H 0.317 0.2733 0.5694 0.063 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.778(4) . ?
S1 C9 1.834(4) . ?
S2 C17 1.772(4) . ?
S2 C23 1.839(4) . ?
O5 C15 1.355(5) . ?
O5 C10 1.445(5) . ?
O2 C29 1.338(5) . ?
O2 C24 1.453(5) . ?
O4 C7 1.229(5) . ?
O1 C31 1.229(5) . ?
O6 C15 1.195(5) . ?
N1 C31 1.349(5) . ?
N1 C18 1.409(5) . ?
N1 H1 0.86 . ?
N2 C7 1.360(5) . ?
N2 C2 1.409(5) . ?
N2 H2 0.86 . ?
C24 C25 1.501(6) . ?
C24 C23 1.516(6) . ?
C24 H24 0.98 . ?
C15 C16 1.491(6) . ?
C31 C32 1.505(6) . ?
C2 C3 1.390(6) . ?
C2 C1 1.403(6) . ?
C7 C8 1.494(6) . ?
C23 C28 1.523(6) . ?
C23 H23 0.98 . ?
C25 C26 1.518(6) . ?
C25 H25A 0.97 . ?
C25 H25B 0.97 . ?
C1 C6 1.391(6) . ?
O3 C29 1.189(6) . ?
C18 C19 1.394(6) . ?
C18 C17 1.409(6) . ?
C28 C27 1.531(6) . ?
C28 H28A 0.97 . ?
C28 H28B 0.97 . ?
C17 C22 1.387(6) . ?
C22 C21 1.384(6) . ?
C22 H22 0.93 . ?
C20 C21 1.384(7) . ?
C20 C19 1.392(6) . ?
C20 H20 0.93 . ?
C32 H32A 0.96 . ?
C32 H32B 0.96 . ?
C32 H32C 0.96 . ?
C9 C14 1.531(6) . ?
C9 C10 1.531(6) . ?
C9 H9 0.98 . ?
C19 H19 0.93 . ?
C10 C11 1.519(6) . ?
C10 H10 0.98 . ?
C14 C13 1.526(6) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C13 C12 1.524(6) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C3 C4 1.382(6) . ?
C3 H3 0.93 . ?
C5 C6 1.381(7) . ?
C5 C4 1.384(7) . ?
C5 H5 0.93 . ?
C26 C27 1.520(6) . ?
C26 H26A 0.97 . ?
C26 H26B 0.97 . ?
C27 H27A 0.97 . ?
C27 H27B 0.97 . ?
C8 H8A 0.96 . ?
C8 H8B 0.96 . ?
C8 H8C 0.96 . ?
C6 H6 0.93 . ?
C12 C11 1.521(6) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C4 H4 0.93 . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C29 C30 1.510(7) . ?
C21 H21 0.93 . ?
C16 H16A 0.96 . ?
C16 H16B 0.96 . ?
C16 H16C 0.96 . ?
C30 H30A 0.96 . ?
C30 H30B 0.96 . ?
C30 H30C 0.96 . ?

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 C9 104.41(19) . . ?
C17 S2 C23 105.10(19) . . ?
C15 O5 C10 118.7(3) . . ?
C29 O2 C24 117.7(4) . . ?
C31 N1 C18 126.3(3) . . ?
C31 N1 H1 116.9 . . ?
C18 N1 H1 116.9 . . ?
C7 N2 C2 126.9(3) . . ?
C7 N2 H2 116.5 . . ?
C2 N2 H2 116.5 . . ?
O2 C24 C25 108.8(3) . . ?
O2 C24 C23 108.1(3) . . ?
C25 C24 C23 112.6(4) . . ?
O2 C24 H24 109.1 . . ?
C25 C24 H24 109.1 . . ?
C23 C24 H24 109.1 . . ?
O6 C15 O5 123.3(4) . . ?
O6 C15 C16 126.3(4) . . ?
O5 C15 C16 110.4(4) . . ?
O1 C31 N1 123.9(4) . . ?
O1 C31 C32 121.3(4) . . ?
N1 C31 C32 114.7(4) . . ?
C3 C2 C1 119.3(4) . . ?
C3 C2 N2 121.3(4) . . ?
C1 C2 N2 119.4(4) . . ?
O4 C7 N2 122.9(4) . . ?
O4 C7 C8 122.1(4) . . ?
N2 C7 C8 115.1(4) . . ?
C24 C23 C28 111.4(4) . . ?
C24 C23 S2 110.8(3) . . ?
C28 C23 S2 108.2(3) . . ?
C24 C23 H23 108.8 . . ?
C28 C23 H23 108.8 . . ?
S2 C23 H23 108.8 . . ?
C24 C25 C26 111.8(4) . . ?
C24 C25 H25A 109.3 . . ?
C26 C25 H25A 109.3 . . ?
C24 C25 H25B 109.3 . . ?
C26 C25 H25B 109.3 . . ?
H25A C25 H25B 107.9 . . ?
C6 C1 C2 119.3(4) . . ?
C6 C1 S1 118.6(3) . . ?
C2 C1 S1 121.9(3) . . ?
C19 C18 C17 119.2(4) . . ?
C19 C18 N1 120.8(4) . . ?
C17 C18 N1 119.9(4) . . ?
C23 C28 C27 112.1(4) . . ?
C23 C28 H28A 109.2 . . ?
C27 C28 H28A 109.2 . . ?
C23 C28 H28B 109.2 . . ?
C27 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C22 C17 C18 119.3(4) . . ?
C22 C17 S2 118.9(3) . . ?
C18 C17 S2 121.5(3) . . ?
C21 C22 C17 121.5(4) . . ?
C21 C22 H22 119.2 . . ?
C17 C22 H22 119.2 . . ?
C21 C20 C19 120.9(4) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C14 C9 C10 111.0(4) . . ?
C14 C9 S1 108.1(3) . . ?
C10 C9 S1 110.9(3) . . ?
C14 C9 H9 108.9 . . ?
C10 C9 H9 108.9 . . ?
S1 C9 H9 108.9 . . ?
C20 C19 C18 120.1(4) . . ?
C20 C19 H19 120 . . ?
C18 C19 H19 120 . . ?
O5 C10 C11 108.3(3) . . ?
O5 C10 C9 107.9(3) . . ?
C11 C10 C9 112.4(4) . . ?
O5 C10 H10 109.4 . . ?
C11 C10 H10 109.4 . . ?
C9 C10 H10 109.4 . . ?
C13 C14 C9 112.4(4) . . ?
C13 C14 H14A 109.1 . . ?
C9 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C9 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C12 C13 C14 110.7(4) . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C4 C3 C2 120.5(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C6 C5 C4 119.4(4) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C25 C26 C27 109.6(4) . . ?
C25 C26 H26A 109.7 . . ?
C27 C26 H26A 109.7 . . ?
C25 C26 H26B 109.7 . . ?
C27 C26 H26B 109.7 . . ?
H26A C26 H26B 108.2 . . ?
C26 C27 C28 110.5(4) . . ?
C26 C27 H27A 109.5 . . ?
C28 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C28 C27 H27B 109.5 . . ?
H27A C27 H27B 108.1 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C6 C1 121.0(4) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C11 C12 C13 110.2(4) . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C3 C4 C5 120.5(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C10 C11 C12 111.7(4) . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
O3 C29 O2 123.1(5) . . ?
O3 C29 C30 125.6(5) . . ?
O2 C29 C30 111.3(4) . . ?
C20 C21 C22 118.9(4) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?



# END of CIF
