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

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

data_160228e
_database_code_depnum_ccdc_archive 'CCDC 1482415'
_audit_update_record             
;
2017-07-26 deposited with the CCDC.
2017-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H15 N O S'
_chemical_formula_weight         341.41

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   8.0270(8)
_cell_length_b                   5.9177(5)
_cell_length_c                   35.133(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.1860(10)
_cell_angle_gamma                90.00
_cell_volume                     1668.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2676
_cell_measurement_theta_min      2.319
_cell_measurement_theta_max      26.987

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9232
_exptl_absorpt_correction_T_max  0.9416
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7857
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_sigmaI/netI    0.0518
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2925
_reflns_number_gt                2140
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0504P)²+1.4235P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0122(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2925
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1411
_refine_ls_wR_factor_gt          0.1308
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2072(3) 0.5975(4) 0.49009(7) 0.0413(6) Uani 1 1 d . . .
O1 O 0.0537(3) 0.8605(3) 0.53900(6) 0.0508(6) Uani 1 1 d . . .
H1 H 0.0857 0.8176 0.5181 0.076 Uiso 1 1 calc R . .
S1 S 0.34277(10) 0.21340(14) 0.50594(2) 0.0456(3) Uani 1 1 d . . .
C1 C 0.2310(3) 0.4554(5) 0.51792(8) 0.0358(7) Uani 1 1 d . . .
C2 C 0.2807(4) 0.5211(5) 0.45652(9) 0.0417(8) Uani 1 1 d . . .
C3 C 0.3601(4) 0.3131(5) 0.45962(9) 0.0426(8) Uani 1 1 d . . .
C4 C 0.4392(4) 0.2115(6) 0.42890(9) 0.0551(9) Uani 1 1 d . . .
H4 H 0.4905 0.0713 0.4313 0.066 Uiso 1 1 calc R . .
C5 C 0.4386(5) 0.3269(8) 0.39485(10) 0.0653(11) Uani 1 1 d . . .
H5 H 0.4917 0.2642 0.3739 0.078 Uiso 1 1 calc R . .
C6 C 0.3605(5) 0.5342(8) 0.39131(10) 0.0696(12) Uani 1 1 d . . .
H6 H 0.3620 0.6083 0.3680 0.084 Uiso 1 1 calc R . .
C7 C 0.2802(4) 0.6334(6) 0.42181(10) 0.0591(10) Uani 1 1 d . . .
H7 H 0.2270 0.7722 0.4191 0.071 Uiso 1 1 calc R . .
C8 C 0.1736(3) 0.4989(5) 0.55675(8) 0.0349(7) Uani 1 1 d . . .
C9 C 0.0903(3) 0.7025(5) 0.56539(9) 0.0393(7) Uani 1 1 d . . .
C10 C 0.0446(4) 0.7488(5) 0.60253(9) 0.0467(8) Uani 1 1 d . . .
H10 H -0.0087 0.8842 0.6082 0.056 Uiso 1 1 calc R . .
C11 C 0.0772(4) 0.5974(5) 0.63108(9) 0.0460(8) Uani 1 1 d . . .
H11 H 0.0460 0.6316 0.6559 0.055 Uiso 1 1 calc R . .
C12 C 0.1571(4) 0.3911(5) 0.62342(8) 0.0403(7) Uani 1 1 d . . .
C13 C 0.2028(4) 0.3463(5) 0.58613(8) 0.0393(7) Uani 1 1 d . . .
H13 H 0.2548 0.2098 0.5806 0.047 Uiso 1 1 calc R . .
C14 C 0.1906(4) 0.2357(5) 0.65386(9) 0.0459(8) Uani 1 1 d . . .
C15 C 0.2139(4) 0.1112(6) 0.67999(9) 0.0472(8) Uani 1 1 d . . .
C16 C 0.2343(4) -0.0352(5) 0.71230(8) 0.0418(8) Uani 1 1 d . . .
C17 C 0.3154(4) -0.2421(6) 0.70956(9) 0.0478(8) Uani 1 1 d . . .
H17 H 0.3590 -0.2874 0.6863 0.057 Uiso 1 1 calc R . .
C18 C 0.3323(4) -0.3813(6) 0.74084(9) 0.0481(8) Uani 1 1 d . . .
H18 H 0.3873 -0.5188 0.7384 0.058 Uiso 1 1 calc R . .
C19 C 0.2683(4) -0.3191(5) 0.77592(9) 0.0428(8) Uani 1 1 d . . .
C20 C 0.1893(4) -0.1126(6) 0.77861(9) 0.0487(8) Uani 1 1 d . . .
H20 H 0.1468 -0.0674 0.8020 0.058 Uiso 1 1 calc R . .
C21 C 0.1718(4) 0.0281(6) 0.74776(9) 0.0468(8) Uani 1 1 d . . .
H21 H 0.1179 0.1663 0.7505 0.056 Uiso 1 1 calc R . .
C22 C 0.2831(5) -0.4722(6) 0.80978(10) 0.0661(11) Uani 1 1 d . . .
H22A H 0.3773 -0.4276 0.8249 0.099 Uiso 1 1 calc R . .
H22B H 0.2978 -0.6252 0.8013 0.099 Uiso 1 1 calc R . .
H22C H 0.1837 -0.4620 0.8248 0.099 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.303(4) . ?
N1 C2 1.396(4) . ?
O1 C9 1.348(3) . ?
O1 H1 0.8200 . ?
S1 C3 1.737(3) . ?
S1 C1 1.742(3) . ?
C1 C8 1.464(4) . ?
C2 C7 1.389(4) . ?
C2 C3 1.390(4) . ?
C3 C4 1.391(5) . ?
C4 C5 1.377(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.383(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.391(4) . ?
C8 C9 1.412(4) . ?
C9 C10 1.384(4) . ?
C10 C11 1.369(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.406(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(4) . ?
C12 C14 1.435(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.191(4) . ?
C15 C16 1.437(4) . ?
C16 C17 1.390(4) . ?
C16 C21 1.396(4) . ?
C17 C18 1.380(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.387(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.380(4) . ?
C19 C22 1.500(4) . ?
C20 C21 1.374(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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 N1 C2 111.3(3) . . ?
C9 O1 H1 109.5 . . ?
C3 S1 C1 89.42(15) . . ?
N1 C1 C8 122.7(3) . . ?
N1 C1 S1 115.1(2) . . ?
C8 C1 S1 122.3(2) . . ?
C7 C2 C3 119.5(3) . . ?
C7 C2 N1 125.9(3) . . ?
C3 C2 N1 114.5(3) . . ?
C2 C3 C4 122.2(3) . . ?
C2 C3 S1 109.7(2) . . ?
C4 C3 S1 128.2(3) . . ?
C5 C4 C3 117.4(4) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
C4 C5 C6 121.2(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C7 121.3(4) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C2 118.5(4) . . ?
C6 C7 H7 120.8 . . ?
C2 C7 H7 120.8 . . ?
C13 C8 C9 118.2(3) . . ?
C13 C8 C1 121.6(3) . . ?
C9 C8 C1 120.1(3) . . ?
O1 C9 C10 117.0(3) . . ?
O1 C9 C8 123.1(3) . . ?
C10 C9 C8 119.9(3) . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 118.0(3) . . ?
C13 C12 C14 122.1(3) . . ?
C11 C12 C14 119.9(3) . . ?
C12 C13 C8 122.2(3) . . ?
C12 C13 H13 118.9 . . ?
C8 C13 H13 118.9 . . ?
C15 C14 C12 177.4(4) . . ?
C14 C15 C16 177.1(4) . . ?
C17 C16 C21 117.9(3) . . ?
C17 C16 C15 121.9(3) . . ?
C21 C16 C15 120.2(3) . . ?
C18 C17 C16 121.0(3) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 120.9(3) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 117.9(3) . . ?
C20 C19 C22 121.1(3) . . ?
C18 C19 C22 121.0(3) . . ?
C21 C20 C19 121.9(3) . . ?
C21 C20 H20 119.0 . . ?
C19 C20 H20 119.0 . . ?
C20 C21 C16 120.3(3) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C2 N1 C1 C8 177.1(2) . . . . ?
C2 N1 C1 S1 -0.8(3) . . . . ?
C3 S1 C1 N1 0.4(2) . . . . ?
C3 S1 C1 C8 -177.5(2) . . . . ?
C1 N1 C2 C7 -179.2(3) . . . . ?
C1 N1 C2 C3 0.8(3) . . . . ?
C7 C2 C3 C4 -0.3(4) . . . . ?
N1 C2 C3 C4 179.7(3) . . . . ?
C7 C2 C3 S1 179.5(2) . . . . ?
N1 C2 C3 S1 -0.5(3) . . . . ?
C1 S1 C3 C2 0.0(2) . . . . ?
C1 S1 C3 C4 179.8(3) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?
S1 C3 C4 C5 -178.8(2) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
C4 C5 C6 C7 0.0(6) . . . . ?
C5 C6 C7 C2 0.6(5) . . . . ?
C3 C2 C7 C6 -0.5(5) . . . . ?
N1 C2 C7 C6 179.5(3) . . . . ?
N1 C1 C8 C13 -178.9(3) . . . . ?
S1 C1 C8 C13 -1.2(4) . . . . ?
N1 C1 C8 C9 -0.7(4) . . . . ?
S1 C1 C8 C9 177.0(2) . . . . ?
C13 C8 C9 O1 -179.1(2) . . . . ?
C1 C8 C9 O1 2.6(4) . . . . ?
C13 C8 C9 C10 2.0(4) . . . . ?
C1 C8 C9 C10 -176.3(3) . . . . ?
O1 C9 C10 C11 -180.0(3) . . . . ?
C8 C9 C10 C11 -1.0(4) . . . . ?
C9 C10 C11 C12 -0.2(5) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C10 C11 C12 C14 179.6(3) . . . . ?
C11 C12 C13 C8 0.6(4) . . . . ?
C14 C12 C13 C8 -178.6(3) . . . . ?
C9 C8 C13 C12 -1.8(4) . . . . ?
C1 C8 C13 C12 176.4(3) . . . . ?
C13 C12 C14 C15 -163(8) . . . . ?
C11 C12 C14 C15 18(8) . . . . ?
C12 C14 C15 C16 17(13) . . . . ?
C14 C15 C16 C17 148(7) . . . . ?
C14 C15 C16 C21 -32(7) . . . . ?
C21 C16 C17 C18 0.5(5) . . . . ?
C15 C16 C17 C18 -179.4(3) . . . . ?
C16 C17 C18 C19 0.2(5) . . . . ?
C17 C18 C19 C20 -0.8(5) . . . . ?
C17 C18 C19 C22 178.7(3) . . . . ?
C18 C19 C20 C21 0.7(5) . . . . ?
C22 C19 C20 C21 -178.8(3) . . . . ?
C19 C20 C21 C16 0.0(5) . . . . ?
C17 C16 C21 C20 -0.7(5) . . . . ?
C15 C16 C21 C20 179.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_160507b
_database_code_depnum_ccdc_archive 'CCDC 1482414'
_audit_update_record             
;
2017-07-26 deposited with the CCDC.
2017-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H13 N O S'
_chemical_formula_weight         327.38

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   4.5363(4)
_cell_length_b                   10.1250(8)
_cell_length_c                   34.375(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1578.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1677
_cell_measurement_theta_min      2.336
_cell_measurement_theta_max      21.307

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9147
_exptl_absorpt_correction_T_max  0.9690
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8041
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0621
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2782
_reflns_number_gt                2007
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0131P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.10(10)
_refine_ls_number_reflns         2782
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.0684
_refine_ls_wR_factor_gt          0.0649
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6274(5) 0.4016(2) 0.05772(5) 0.0430(6) Uani 1 1 d . . .
O1 O 0.2692(5) 0.54461(17) 0.01592(4) 0.0613(6) Uani 1 1 d . . .
H1 H 0.3864 0.4851 0.0207 0.092 Uiso 1 1 calc R . .
S1 S 0.67885(18) 0.41454(7) 0.132004(17) 0.0533(2) Uani 1 1 d . . .
C1 C 0.5353(6) 0.4679(2) 0.08764(7) 0.0417(7) Uani 1 1 d . . .
C2 C 0.8209(7) 0.3037(3) 0.06813(7) 0.0450(7) Uani 1 1 d . . .
C3 C 0.8773(7) 0.2945(3) 0.10778(7) 0.0451(8) Uani 1 1 d . . .
C4 C 1.0651(7) 0.2000(3) 0.12248(8) 0.0590(9) Uani 1 1 d . . .
H4 H 1.0997 0.1939 0.1491 0.071 Uiso 1 1 calc R . .
C5 C 1.1995(7) 0.1152(3) 0.09707(8) 0.0615(8) Uani 1 1 d . . .
H5 H 1.3267 0.0507 0.1065 0.074 Uiso 1 1 calc R . .
C6 C 1.1485(7) 0.1239(3) 0.05737(8) 0.0611(8) Uani 1 1 d . . .
H6 H 1.2428 0.0658 0.0405 0.073 Uiso 1 1 calc R . .
C7 C 0.9609(7) 0.2173(3) 0.04273(8) 0.0526(8) Uani 1 1 d . . .
H7 H 0.9275 0.2229 0.0161 0.063 Uiso 1 1 calc R . .
C8 C 0.3295(6) 0.5765(2) 0.08481(6) 0.0396(6) Uani 1 1 d . . .
C9 C 0.2048(7) 0.6096(2) 0.04879(7) 0.0447(7) Uani 1 1 d . . .
C10 C 0.0070(7) 0.7127(3) 0.04616(8) 0.0536(8) Uani 1 1 d . . .
H10 H -0.0756 0.7344 0.0222 0.064 Uiso 1 1 calc R . .
C11 C -0.0678(7) 0.7829(3) 0.07860(8) 0.0522(8) Uani 1 1 d . . .
H11 H -0.2013 0.8523 0.0764 0.063 Uiso 1 1 calc R . .
C12 C 0.0506(7) 0.7532(3) 0.11468(8) 0.0471(8) Uani 1 1 d . . .
C13 C 0.2513(7) 0.6510(3) 0.11703(7) 0.0479(8) Uani 1 1 d . . .
H13 H 0.3366 0.6315 0.1410 0.058 Uiso 1 1 calc R . .
C14 C -0.0312(7) 0.8269(3) 0.14833(8) 0.0564(9) Uani 1 1 d . . .
C15 C -0.1052(7) 0.8903(3) 0.17573(8) 0.0575(9) Uani 1 1 d . . .
C16 C -0.1957(8) 0.9732(3) 0.20701(7) 0.0502(8) Uani 1 1 d . . .
C17 C -0.0874(8) 0.9577(3) 0.24402(8) 0.0724(12) Uani 1 1 d . . .
H17 H 0.0471 0.8908 0.2493 0.087 Uiso 1 1 calc R . .
C18 C -0.1775(9) 1.0411(3) 0.27320(8) 0.0805(11) Uani 1 1 d . . .
H18 H -0.1049 1.0289 0.2982 0.097 Uiso 1 1 calc R . .
C19 C -0.3675(8) 1.1394(3) 0.26638(9) 0.0708(10) Uani 1 1 d . . .
H19 H -0.4275 1.1948 0.2865 0.085 Uiso 1 1 calc R . .
C20 C -0.4712(8) 1.1573(3) 0.22994(10) 0.0874(12) Uani 1 1 d . . .
H20 H -0.5993 1.2268 0.2248 0.105 Uiso 1 1 calc R . .
C21 C -0.3887(8) 1.0735(3) 0.20040(8) 0.0751(11) Uani 1 1 d . . .
H21 H -0.4659 1.0856 0.1756 0.090 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.297(3) . ?
N1 C2 1.372(3) . ?
O1 C9 1.340(2) . ?
O1 H1 0.8200 . ?
S1 C3 1.726(3) . ?
S1 C1 1.744(3) . ?
C1 C8 1.446(3) . ?
C2 C7 1.389(3) . ?
C2 C3 1.390(3) . ?
C3 C4 1.377(3) . ?
C4 C5 1.368(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.368(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.386(3) . ?
C8 C9 1.402(3) . ?
C9 C10 1.379(4) . ?
C10 C11 1.365(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(3) . ?
C12 C14 1.426(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.188(3) . ?
C15 C16 1.424(3) . ?
C16 C21 1.361(4) . ?
C16 C17 1.373(3) . ?
C17 C18 1.373(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.338(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.350(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.375(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 111.9(2) . . ?
C9 O1 H1 109.5 . . ?
C3 S1 C1 89.48(13) . . ?
N1 C1 C8 123.3(2) . . ?
N1 C1 S1 114.4(2) . . ?
C8 C1 S1 122.37(19) . . ?
N1 C2 C7 125.7(2) . . ?
N1 C2 C3 114.9(2) . . ?
C7 C2 C3 119.4(3) . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 S1 129.4(2) . . ?
C2 C3 S1 109.3(2) . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C2 119.2(3) . . ?
C6 C7 H7 120.4 . . ?
C2 C7 H7 120.4 . . ?
C13 C8 C9 118.2(3) . . ?
C13 C8 C1 121.7(2) . . ?
C9 C8 C1 120.1(2) . . ?
O1 C9 C10 117.3(2) . . ?
O1 C9 C8 122.7(3) . . ?
C10 C9 C8 120.1(2) . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 121.5(3) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C13 C12 C11 118.1(2) . . ?
C13 C12 C14 121.1(3) . . ?
C11 C12 C14 120.8(3) . . ?
C12 C13 C8 122.0(2) . . ?
C12 C13 H13 119.0 . . ?
C8 C13 H13 119.0 . . ?
C15 C14 C12 178.0(3) . . ?
C14 C15 C16 176.5(3) . . ?
C21 C16 C17 118.0(3) . . ?
C21 C16 C15 119.9(3) . . ?
C17 C16 C15 122.0(3) . . ?
C16 C17 C18 120.0(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 121.4(3) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C20 119.1(3) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C19 C20 C21 120.5(3) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C16 C21 C20 120.8(3) . . ?
C16 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?

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
C2 N1 C1 C8 -180.0(2) . . . . ?
C2 N1 C1 S1 -0.3(3) . . . . ?
C3 S1 C1 N1 0.1(2) . . . . ?
C3 S1 C1 C8 179.8(2) . . . . ?
C1 N1 C2 C7 -179.0(3) . . . . ?
C1 N1 C2 C3 0.4(3) . . . . ?
N1 C2 C3 C4 179.4(2) . . . . ?
C7 C2 C3 C4 -1.2(4) . . . . ?
N1 C2 C3 S1 -0.3(3) . . . . ?
C7 C2 C3 S1 179.1(2) . . . . ?
C1 S1 C3 C4 -179.5(3) . . . . ?
C1 S1 C3 C2 0.1(2) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
S1 C3 C4 C5 -179.7(2) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C7 -0.4(5) . . . . ?
C5 C6 C7 C2 -0.1(4) . . . . ?
N1 C2 C7 C6 -179.8(3) . . . . ?
C3 C2 C7 C6 0.8(4) . . . . ?
N1 C1 C8 C13 -175.5(3) . . . . ?
S1 C1 C8 C13 4.9(4) . . . . ?
N1 C1 C8 C9 4.1(4) . . . . ?
S1 C1 C8 C9 -175.6(2) . . . . ?
C13 C8 C9 O1 179.2(2) . . . . ?
C1 C8 C9 O1 -0.4(4) . . . . ?
C13 C8 C9 C10 -0.9(4) . . . . ?
C1 C8 C9 C10 179.5(3) . . . . ?
O1 C9 C10 C11 -180.0(2) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C10 C11 C12 C13 0.9(4) . . . . ?
C10 C11 C12 C14 -179.6(3) . . . . ?
C11 C12 C13 C8 -1.7(4) . . . . ?
C14 C12 C13 C8 178.7(3) . . . . ?
C9 C8 C13 C12 1.7(4) . . . . ?
C1 C8 C13 C12 -178.7(2) . . . . ?
C13 C12 C14 C15 -176(100) . . . . ?
C11 C12 C14 C15 4(10) . . . . ?
C12 C14 C15 C16 -37(14) . . . . ?
C14 C15 C16 C21 32(6) . . . . ?
C14 C15 C16 C17 -146(6) . . . . ?
C21 C16 C17 C18 0.9(5) . . . . ?
C15 C16 C17 C18 179.1(3) . . . . ?
C16 C17 C18 C19 -0.9(6) . . . . ?
C17 C18 C19 C20 -0.4(6) . . . . ?
C18 C19 C20 C21 1.7(6) . . . . ?
C17 C16 C21 C20 0.4(5) . . . . ?
C15 C16 C21 C20 -177.8(3) . . . . ?
C19 C20 C21 C16 -1.7(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.036
