# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_POLY1
_database_code_depnum_ccdc_archive 'CCDC 1453057'
_audit_update_record             
;
2016-02-12 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 N3 S2'
_chemical_formula_weight         299.40

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   P21/n

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

_cell_length_a                   10.5847(6)
_cell_length_b                   8.8751(5)
_cell_length_c                   16.2063(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.210(6)
_cell_angle_gamma                90.00
_cell_volume                     1461.91(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1714
_cell_measurement_theta_min      3.0414
_cell_measurement_theta_max      28.5733

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5533
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2645
_reflns_number_gt                1928
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0000P)²+1.6600P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2645
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.0956
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.005
_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
S2 S 0.56510(9) 0.36005(13) 0.41147(6) 0.0777(3) Uani 1 1 d . . .
S1 S 0.75587(9) 0.57811(12) 0.72629(6) 0.0735(3) Uani 1 1 d . . .
N2 N 0.6902(3) 0.4525(3) 0.56760(16) 0.0577(7) Uani 1 1 d . . .
N3 N 0.8119(3) 0.3068(3) 0.50039(18) 0.0616(8) Uani 1 1 d . . .
N1 N 0.9003(3) 0.4049(3) 0.66460(17) 0.0673(8) Uani 1 1 d . . .
C4 C 0.7861(3) 0.4674(3) 0.64601(19) 0.0531(8) Uani 1 1 d . . .
C15 C 0.8337(3) 0.0567(4) 0.4447(2) 0.0541(8) Uani 1 1 d . . .
C10 C 0.8558(3) -0.0375(4) 0.3792(2) 0.0606(9) Uani 1 1 d . . .
C5 C 0.6972(3) 0.3716(4) 0.49685(19) 0.0547(8) Uani 1 1 d . . .
C6 C 0.8329(3) 0.2129(4) 0.4325(2) 0.0560(8) Uani 1 1 d . . .
C2 C 0.9123(3) 0.5361(4) 0.7907(2) 0.0626(9) Uani 1 1 d . . .
C1 C 0.9651(3) 0.5995(5) 0.8790(2) 0.0906(13) Uani 1 1 d . . .
H1A H 0.9089 0.5706 0.9137 0.136 Uiso 1 1 calc R . .
H1B H 0.9681 0.7074 0.8758 0.136 Uiso 1 1 calc R . .
H1C H 1.0521 0.5612 0.9043 0.136 Uiso 1 1 calc R . .
C3 C 0.9697(3) 0.4449(4) 0.7473(2) 0.0701(10) Uani 1 1 d . . .
H3 H 1.0543 0.4088 0.7718 0.084 Uiso 1 1 calc R . .
C14 C 0.8141(3) -0.0140(4) 0.5197(2) 0.0624(9) Uani 1 1 d . . .
H14 H 0.8002 0.0451 0.5637 0.075 Uiso 1 1 calc R . .
C7 C 0.8550(3) 0.2729(4) 0.3621(2) 0.0703(10) Uani 1 1 d . . .
H7 H 0.8548 0.3771 0.3560 0.084 Uiso 1 1 calc R . .
C13 C 0.8156(4) -0.1654(5) 0.5271(3) 0.0870(12) Uani 1 1 d . . .
H13 H 0.8027 -0.2094 0.5761 0.104 Uiso 1 1 calc R . .
C9 C 0.8786(3) 0.0269(6) 0.3059(2) 0.0835(13) Uani 1 1 d . . .
H9 H 0.8938 -0.0345 0.2631 0.100 Uiso 1 1 calc R . .
C11 C 0.8558(3) -0.1952(5) 0.3924(3) 0.0853(13) Uani 1 1 d . . .
H11 H 0.8700 -0.2592 0.3504 0.102 Uiso 1 1 calc R . .
C8 C 0.8787(4) 0.1815(6) 0.2970(2) 0.0884(13) Uani 1 1 d . . .
H8 H 0.8942 0.2249 0.2485 0.106 Uiso 1 1 calc R . .
C12 C 0.8359(4) -0.2547(5) 0.4635(4) 0.1038(16) Uani 1 1 d . . .
H12 H 0.8359 -0.3589 0.4697 0.125 Uiso 1 1 calc R . .
H2 H 0.610(3) 0.495(4) 0.563(2) 0.084(12) Uiso 1 1 d . . .
H3A H 0.868(4) 0.303(4) 0.555(2) 0.097(13) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 C5 1.673(3) . ?
S1 C4 1.730(3) . ?
S1 C2 1.734(3) . ?
N2 C5 1.373(4) . ?
N2 C4 1.394(4) . ?
N3 C5 1.330(4) . ?
N3 C6 1.445(4) . ?
N1 C4 1.288(4) . ?
N1 C3 1.382(4) . ?
C15 C6 1.401(4) . ?
C15 C10 1.421(4) . ?
C15 C14 1.433(4) . ?
C10 C9 1.399(5) . ?
C10 C11 1.416(5) . ?
C6 C7 1.338(4) . ?
C2 C3 1.326(4) . ?
C2 C1 1.493(4) . ?
C14 C13 1.349(5) . ?
C7 C8 1.407(5) . ?
C13 C12 1.364(6) . ?
C9 C8 1.379(6) . ?
C11 C12 1.336(6) . ?

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
C4 S1 C2 89.12(15) . . ?
C5 N2 C4 128.0(3) . . ?
C5 N3 C6 123.3(3) . . ?
C4 N1 C3 109.0(3) . . ?
N1 C4 N2 124.7(3) . . ?
N1 C4 S1 115.3(2) . . ?
N2 C4 S1 120.0(2) . . ?
C6 C15 C10 118.2(3) . . ?
C6 C15 C14 123.8(3) . . ?
C10 C15 C14 118.0(3) . . ?
C9 C10 C11 122.7(4) . . ?
C9 C10 C15 119.8(3) . . ?
C11 C10 C15 117.5(4) . . ?
N3 C5 N2 116.9(3) . . ?
N3 C5 S2 123.5(2) . . ?
N2 C5 S2 119.7(2) . . ?
C7 C6 C15 121.2(3) . . ?
C7 C6 N3 121.4(3) . . ?
C15 C6 N3 117.4(3) . . ?
C3 C2 C1 129.4(3) . . ?
C3 C2 S1 108.3(2) . . ?
C1 C2 S1 122.3(3) . . ?
C2 C3 N1 118.3(3) . . ?
C13 C14 C15 120.7(4) . . ?
C6 C7 C8 121.4(4) . . ?
C14 C13 C12 120.9(4) . . ?
C8 C9 C10 120.0(4) . . ?
C12 C11 C10 121.8(4) . . ?
C9 C8 C7 119.3(4) . . ?
C11 C12 C13 121.2(5) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.044





####################################################################### 
# 
# 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_poly2
_database_code_depnum_ccdc_archive 'CCDC 1453058'
_audit_update_record             
;
2016-02-12 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 N3 S2'
_chemical_formula_weight         299.40

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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'
'-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                   22.884(3)
_cell_length_b                   8.3045(6)
_cell_length_c                   15.2009(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.047(8)
_cell_angle_gamma                90.00
_cell_volume                     2835.3(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1824
_cell_measurement_theta_min      3.5495
_cell_measurement_theta_max      28.7109

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    0.368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4309
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.56
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2511
_reflns_number_gt                1696
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0775P)²+0.0001P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2511
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.1222
_refine_ls_wR_factor_gt          0.1107
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
S2 S 0.43253(4) -0.04799(8) 0.38035(4) 0.0671(3) Uani 1 1 d . . .
S1 S 0.59682(3) 0.37902(8) 0.50260(3) 0.0506(3) Uani 1 1 d . . .
N1 N 0.51542(10) 0.4582(2) 0.36901(13) 0.0500(6) Uani 1 1 d . . .
N2 N 0.50943(9) 0.1877(2) 0.41732(12) 0.0454(5) Uani 1 1 d . . .
N3 N 0.43593(9) 0.2340(2) 0.29473(11) 0.0417(5) Uani 1 1 d . . .
C8 C 0.31212(14) 0.0624(3) 0.12661(14) 0.0563(7) Uani 1 1 d . . .
H8 H 0.3017 -0.0346 0.0971 0.068 Uiso 1 1 calc R . .
C5 C 0.45933(11) 0.1336(3) 0.36094(13) 0.0424(6) Uani 1 1 d . . .
C7 C 0.36666(13) 0.0744(3) 0.18704(14) 0.0505(7) Uani 1 1 d . . .
H7 H 0.3924 -0.0131 0.1968 0.061 Uiso 1 1 calc R . .
C14 C 0.35806(12) 0.5048(3) 0.25691(13) 0.0429(6) Uani 1 1 d . . .
H14 H 0.3939 0.5183 0.2970 0.052 Uiso 1 1 calc R . .
C15 C 0.34413(10) 0.3528(2) 0.21486(12) 0.0367(5) Uani 1 1 d . . .
C6 C 0.38148(10) 0.2164(3) 0.23149(12) 0.0383(6) Uani 1 1 d . . .
C10 C 0.28909(11) 0.3378(3) 0.15320(12) 0.0424(6) Uani 1 1 d . . .
C12 C 0.26496(13) 0.6137(3) 0.17944(16) 0.0593(8) Uani 1 1 d . . .
H12 H 0.2387 0.7001 0.1685 0.071 Uiso 1 1 calc R . .
C13 C 0.31952(13) 0.6306(3) 0.23917(15) 0.0537(7) Uani 1 1 d . . .
H13 H 0.3295 0.7292 0.2670 0.064 Uiso 1 1 calc R . .
C9 C 0.27460(11) 0.1883(3) 0.11059(13) 0.0516(7) Uani 1 1 d . . .
H9 H 0.2385 0.1766 0.0708 0.062 Uiso 1 1 calc R . .
C3 C 0.55067(13) 0.5919(3) 0.39448(16) 0.0549(7) Uani 1 1 d . . .
H3 H 0.5431 0.6897 0.3647 0.066 Uiso 1 1 calc R . .
C2 C 0.59604(13) 0.5746(3) 0.46380(15) 0.0497(7) Uani 1 1 d . . .
C11 C 0.25070(13) 0.4713(3) 0.13779(15) 0.0558(7) Uani 1 1 d . . .
H11 H 0.2146 0.4614 0.0979 0.067 Uiso 1 1 calc R . .
C1 C 0.64161(14) 0.6941(4) 0.50575(17) 0.0727(9) Uani 1 1 d . . .
H1A H 0.6304 0.7994 0.4825 0.109 Uiso 1 1 calc R . .
H1B H 0.6796 0.6657 0.4923 0.109 Uiso 1 1 calc R . .
H1C H 0.6442 0.6939 0.5695 0.109 Uiso 1 1 calc R . .
C4 C 0.53456(11) 0.3390(3) 0.42186(13) 0.0394(5) Uani 1 1 d . . .
H2 H 0.5219(15) 0.122(3) 0.458(2) 0.081(10) Uiso 1 1 d . . .
H3A H 0.4525(14) 0.329(3) 0.2966(18) 0.076(9) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 C5 1.676(2) . ?
S1 C4 1.725(2) . ?
S1 C2 1.727(3) . ?
N1 C4 1.297(3) . ?
N1 C3 1.383(3) . ?
N2 C5 1.369(3) . ?
N2 C4 1.378(3) . ?
N3 C5 1.337(3) . ?
N3 C6 1.428(3) . ?
C8 C9 1.346(4) . ?
C8 C7 1.404(4) . ?
C7 C6 1.369(3) . ?
C14 C13 1.361(3) . ?
C14 C15 1.423(3) . ?
C15 C6 1.413(3) . ?
C15 C10 1.424(3) . ?
C10 C11 1.406(3) . ?
C10 C9 1.410(3) . ?
C12 C11 1.352(4) . ?
C12 C13 1.403(4) . ?
C3 C2 1.338(4) . ?
C2 C1 1.491(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 S1 C2 89.16(12) . . ?
C4 N1 C3 109.25(19) . . ?
C5 N2 C4 128.46(19) . . ?
C5 N3 C6 127.9(2) . . ?
C9 C8 C7 121.3(2) . . ?
N3 C5 N2 115.7(2) . . ?
N3 C5 S2 125.90(18) . . ?
N2 C5 S2 118.42(16) . . ?
C6 C7 C8 119.3(2) . . ?
C13 C14 C15 120.7(2) . . ?
C6 C15 C14 123.7(2) . . ?
C6 C15 C10 118.40(19) . . ?
C14 C15 C10 117.9(2) . . ?
C7 C6 C15 121.2(2) . . ?
C7 C6 N3 121.5(2) . . ?
C15 C6 N3 117.25(18) . . ?
C11 C10 C9 122.2(2) . . ?
C11 C10 C15 119.1(2) . . ?
C9 C10 C15 118.7(2) . . ?
C11 C12 C13 119.7(2) . . ?
C14 C13 C12 120.9(2) . . ?
C8 C9 C10 121.0(2) . . ?
C2 C3 N1 117.2(2) . . ?
C3 C2 C1 129.8(3) . . ?
C3 C2 S1 109.0(2) . . ?
C1 C2 S1 121.3(2) . . ?
C12 C11 C10 121.7(2) . . ?
N1 C4 N2 125.2(2) . . ?
N1 C4 S1 115.34(17) . . ?
N2 C4 S1 119.42(16) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1453059'
_audit_update_record             
;
2016-02-12 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 N3 S2'
_chemical_formula_weight         299.40

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6645(6)
_cell_length_b                   7.8706(7)
_cell_length_c                   12.6909(12)
_cell_angle_alpha                107.745(6)
_cell_angle_beta                 99.244(7)
_cell_angle_gamma                97.038(6)
_cell_volume                     707.60(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2376
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      24.76

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            10509
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2531
_reflns_number_gt                1890
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0700P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2531
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.1170
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
S2 S 1.47151(8) 0.46441(9) 0.32017(5) 0.0611(2) Uani 1 1 d . . .
S1 S 1.06906(8) 0.32471(9) 0.59308(5) 0.0617(2) Uani 1 1 d . . .
C15 C 0.9934(2) 0.2656(2) 0.05933(16) 0.0396(5) Uani 1 1 d . . .
C6 C 1.1477(3) 0.2251(3) 0.12026(16) 0.0418(5) Uani 1 1 d . . .
C5 C 1.2802(3) 0.3412(3) 0.32538(16) 0.0445(5) Uani 1 1 d . . .
C4 C 1.0898(3) 0.2737(3) 0.45374(16) 0.0429(5) Uani 1 1 d . . .
C7 C 1.2801(3) 0.1623(3) 0.06812(18) 0.0476(5) Uani 1 1 d . . .
H7 H 1.3786 0.1350 0.1088 0.057 Uiso 1 1 calc R . .
C10 C 0.9841(3) 0.2404(3) -0.05694(17) 0.0441(5) Uani 1 1 d . . .
C9 C 1.1254(3) 0.1773(3) -0.10817(18) 0.0502(5) Uani 1 1 d . . .
H9 H 1.1203 0.1621 -0.1843 0.060 Uiso 1 1 calc R . .
C14 C 0.8499(3) 0.3277(3) 0.10944(18) 0.0477(5) Uani 1 1 d . . .
H14 H 0.8537 0.3434 0.1855 0.057 Uiso 1 1 calc R . .
C8 C 1.2679(3) 0.1388(3) -0.04719(19) 0.0522(6) Uani 1 1 d . . .
H8 H 1.3591 0.0962 -0.0822 0.063 Uiso 1 1 calc R . .
C11 C 0.8318(3) 0.2812(3) -0.1179(2) 0.0579(6) Uani 1 1 d . . .
H11 H 0.8240 0.2671 -0.1941 0.069 Uiso 1 1 calc R . .
C12 C 0.6977(3) 0.3401(3) -0.0672(2) 0.0626(7) Uani 1 1 d . . .
H12 H 0.5984 0.3647 -0.1088 0.075 Uiso 1 1 calc R . .
C1 C 0.6328(3) 0.0287(4) 0.3605(2) 0.0685(7) Uani 1 1 d . . .
H1A H 0.6486 -0.0913 0.3202 0.103 Uiso 1 1 calc R . .
H1B H 0.5878 0.0857 0.3074 0.103 Uiso 1 1 calc R . .
H1C H 0.5486 0.0216 0.4081 0.103 Uiso 1 1 calc R . .
C2 C 0.8084(3) 0.1374(3) 0.43133(18) 0.0502(5) Uani 1 1 d . . .
C13 C 0.7079(3) 0.3641(3) 0.0472(2) 0.0561(6) Uani 1 1 d . . .
H13 H 0.6156 0.4058 0.0812 0.067 Uiso 1 1 calc R . .
C3 C 0.8525(3) 0.2048(4) 0.5446(2) 0.0668(7) Uani 1 1 d . . .
H3 H 0.7750 0.1885 0.5915 0.080 Uiso 1 1 calc R . .
N1 N 0.9468(2) 0.1759(2) 0.37878(14) 0.0466(4) Uani 1 1 d . . .
N3 N 1.1508(2) 0.2422(2) 0.23607(13) 0.0474(4) Uani 1 1 d . . .
H3A H 1.0601 0.1827 0.2496 0.057 Uiso 1 1 calc R . .
N2 N 1.2475(2) 0.3409(2) 0.42910(14) 0.0515(5) Uani 1 1 d . . .
H2 H 1.3368 0.3887 0.4856 0.062 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
S2 C5 1.678(2) . ?
S1 C3 1.720(3) . ?
S1 C4 1.728(2) . ?
C15 C10 1.416(3) . ?
C15 C14 1.421(3) . ?
C15 C6 1.431(3) . ?
C6 C7 1.360(3) . ?
C6 N3 1.430(2) . ?
C5 N3 1.337(2) . ?
C5 N2 1.380(3) . ?
C4 N1 1.308(2) . ?
C4 N2 1.379(3) . ?
C7 C8 1.404(3) . ?
C10 C9 1.415(3) . ?
C10 C11 1.421(3) . ?
C9 C8 1.355(3) . ?
C14 C13 1.353(3) . ?
C11 C12 1.354(3) . ?
C12 C13 1.393(3) . ?
C1 C2 1.487(3) . ?
C2 C3 1.341(3) . ?
C2 N1 1.391(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 S1 C4 88.09(11) . . ?
C10 C15 C14 118.94(19) . . ?
C10 C15 C6 117.77(18) . . ?
C14 C15 C6 123.29(18) . . ?
C7 C6 C15 121.21(19) . . ?
C7 C6 N3 121.59(19) . . ?
C15 C6 N3 117.07(17) . . ?
N3 C5 N2 115.35(18) . . ?
N3 C5 S2 125.47(16) . . ?
N2 C5 S2 119.17(14) . . ?
N1 C4 N2 125.18(18) . . ?
N1 C4 S1 115.12(16) . . ?
N2 C4 S1 119.66(14) . . ?
C6 C7 C8 119.9(2) . . ?
C9 C10 C15 119.56(19) . . ?
C9 C10 C11 122.3(2) . . ?
C15 C10 C11 118.1(2) . . ?
C8 C9 C10 120.5(2) . . ?
C13 C14 C15 120.4(2) . . ?
C9 C8 C7 121.0(2) . . ?
C12 C11 C10 121.2(2) . . ?
C11 C12 C13 120.2(2) . . ?
C3 C2 N1 113.9(2) . . ?
C3 C2 C1 126.9(2) . . ?
N1 C2 C1 119.18(19) . . ?
C14 C13 C12 121.1(2) . . ?
C2 C3 S1 112.13(18) . . ?
C4 N1 C2 110.76(18) . . ?
C5 N3 C6 126.64(17) . . ?
C4 N2 C5 128.30(17) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.039



####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1453060'
_audit_update_record             
;
2016-02-12 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 N3 S2'
_chemical_formula_weight         299.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6357(5)
_cell_length_b                   8.2456(8)
_cell_length_c                   11.8464(6)
_cell_angle_alpha                97.352(6)
_cell_angle_beta                 104.485(5)
_cell_angle_gamma                96.981(7)
_cell_volume                     707.00(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2016
_cell_measurement_theta_min      3.7170
_cell_measurement_theta_max      28.0720

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4719
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.33
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2553
_reflns_number_gt                2052
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0000P)²+0.3563P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2553
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0709
_refine_ls_wR_factor_gt          0.0648
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
S2 S 0.05467(9) 0.53717(7) 0.68908(5) 0.05739(18) Uani 1 1 d . . .
S1 S 0.12489(10) 0.87805(9) 0.35421(5) 0.0661(2) Uani 1 1 d . . .
N3 N 0.2506(3) 0.8380(2) 0.74525(15) 0.0504(5) Uani 1 1 d . . .
N2 N 0.1315(3) 0.7390(2) 0.54702(15) 0.0508(5) Uani 1 1 d . . .
N1 N 0.2797(3) 1.0166(2) 0.56933(15) 0.0499(5) Uani 1 1 d . . .
C4 C 0.1869(3) 0.8797(3) 0.50518(18) 0.0460(5) Uani 1 1 d . . .
C5 C 0.1528(3) 0.7152(3) 0.66128(17) 0.0452(5) Uani 1 1 d . . .
C6 C 0.2968(3) 0.8236(2) 0.86846(17) 0.0431(5) Uani 1 1 d . . .
C15 C 0.4582(3) 0.7601(2) 0.91628(17) 0.0424(5) Uani 1 1 d . . .
C2 C 0.3055(3) 1.1328(3) 0.4972(2) 0.0556(6) Uani 1 1 d . . .
C10 C 0.5053(3) 0.7525(3) 1.03913(18) 0.0469(5) Uani 1 1 d . . .
C9 C 0.3876(3) 0.8054(3) 1.10642(19) 0.0565(6) Uani 1 1 d . . .
H9 H 0.4168 0.8002 1.1868 0.068 Uiso 1 1 calc R . .
C14 C 0.5737(3) 0.7033(3) 0.8488(2) 0.0549(6) Uani 1 1 d . . .
H14 H 0.5446 0.7065 0.7682 0.066 Uiso 1 1 calc R . .
C7 C 0.1885(3) 0.8734(3) 0.93573(19) 0.0533(6) Uani 1 1 d . . .
H7 H 0.0831 0.9148 0.9020 0.064 Uiso 1 1 calc R . .
C8 C 0.2346(3) 0.8629(3) 1.05655(19) 0.0588(6) Uani 1 1 d . . .
H8 H 0.1586 0.8960 1.1024 0.071 Uiso 1 1 calc R . .
C12 C 0.7724(4) 0.6378(3) 1.0227(2) 0.0702(7) Uani 1 1 d . . .
H12 H 0.8777 0.5972 1.0578 0.084 Uiso 1 1 calc R . .
C3 C 0.2331(4) 1.0785(3) 0.3820(2) 0.0668(7) Uani 1 1 d . . .
H3 H 0.2407 1.1423 0.3236 0.080 Uiso 1 1 calc R . .
C13 C 0.7278(3) 0.6437(3) 0.9011(2) 0.0664(7) Uani 1 1 d . . .
H13 H 0.8034 0.6069 0.8560 0.080 Uiso 1 1 calc R . .
C11 C 0.6649(3) 0.6901(3) 1.0886(2) 0.0633(7) Uani 1 1 d . . .
H11 H 0.6968 0.6849 1.1690 0.076 Uiso 1 1 calc R . .
C1 C 0.4053(4) 1.3016(3) 0.5538(2) 0.0782(8) Uani 1 1 d . . .
H1A H 0.4101 1.3690 0.4939 0.117 Uiso 1 1 calc R . .
H1B H 0.5276 1.2942 0.5971 0.117 Uiso 1 1 calc R . .
H1C H 0.3424 1.3507 0.6068 0.117 Uiso 1 1 calc R . .
H2 H 0.071(3) 0.658(3) 0.4966(18) 0.047(7) Uiso 1 1 d . . .
H3A H 0.297(3) 0.923(3) 0.723(2) 0.066(8) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 C5 1.674(2) . ?
S1 C3 1.708(3) . ?
S1 C4 1.730(2) . ?
N3 C5 1.327(3) . ?
N3 C6 1.437(2) . ?
N2 C5 1.365(2) . ?
N2 C4 1.379(3) . ?
N1 C4 1.293(3) . ?
N1 C2 1.390(3) . ?
C6 C7 1.347(3) . ?
C6 C15 1.414(3) . ?
C15 C14 1.412(3) . ?
C15 C10 1.421(3) . ?
C2 C3 1.332(3) . ?
C2 C1 1.489(3) . ?
C10 C11 1.402(3) . ?
C10 C9 1.413(3) . ?
C9 C8 1.342(3) . ?
C14 C13 1.365(3) . ?
C7 C8 1.403(3) . ?
C12 C11 1.337(3) . ?
C12 C13 1.405(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 S1 C4 87.71(11) . . ?
C5 N3 C6 122.61(19) . . ?
C5 N2 C4 128.8(2) . . ?
C4 N1 C2 109.73(19) . . ?
N1 C4 N2 125.72(19) . . ?
N1 C4 S1 115.90(16) . . ?
N2 C4 S1 118.36(17) . . ?
N3 C5 N2 117.03(19) . . ?
N3 C5 S2 123.44(16) . . ?
N2 C5 S2 119.53(16) . . ?
C7 C6 C15 121.73(19) . . ?
C7 C6 N3 119.7(2) . . ?
C15 C6 N3 118.53(19) . . ?
C14 C15 C6 123.73(19) . . ?
C14 C15 C10 118.5(2) . . ?
C6 C15 C10 117.75(19) . . ?
C3 C2 N1 114.6(2) . . ?
C3 C2 C1 126.8(2) . . ?
N1 C2 C1 118.5(2) . . ?
C11 C10 C9 122.5(2) . . ?
C11 C10 C15 118.8(2) . . ?
C9 C10 C15 118.7(2) . . ?
C8 C9 C10 121.3(2) . . ?
C13 C14 C15 120.5(2) . . ?
C6 C7 C8 120.1(2) . . ?
C9 C8 C7 120.5(2) . . ?
C11 C12 C13 120.6(2) . . ?
C2 C3 S1 112.06(18) . . ?
C14 C13 C12 120.1(2) . . ?
C12 C11 C10 121.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1453061'
_audit_update_record             
;
2016-02-12 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 N3 S2'
_chemical_formula_weight         297.39

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   12.4078(12)
_cell_length_b                   15.0565(12)
_cell_length_c                   15.0342(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.887(8)
_cell_angle_gamma                90.00
_cell_volume                     2782.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1996
_cell_measurement_theta_min      2.9915
_cell_measurement_theta_max      28.7227

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11096
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0824
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         25.25
_reflns_number_total             5028
_reflns_number_gt                3055
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0000P)²+12.9900P] 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_number_reflns         5028
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1438
_refine_ls_R_factor_gt           0.0954
_refine_ls_wR_factor_ref         0.1939
_refine_ls_wR_factor_gt          0.1797
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.47516(16) 0.11998(13) 0.69818(12) 0.0563(5) Uani 1 1 d . . .
S3 S 0.27140(15) 1.02758(13) 0.20143(12) 0.0577(5) Uani 1 1 d . . .
S4 S 0.11873(16) 0.93052(14) 0.46811(12) 0.0625(6) Uani 1 1 d . . .
S2 S 0.61027(17) 0.24663(15) 0.43430(13) 0.0693(6) Uani 1 1 d . . .
C18 C 0.4420(6) 1.1168(5) 0.2520(5) 0.0552(18) Uani 1 1 d . . .
H18 H 0.5051 1.1501 0.2511 0.066 Uiso 1 1 calc R . .
C19 C 0.3162(5) 1.0428(4) 0.3150(4) 0.0443(16) Uani 1 1 d . . .
C6 C 0.7092(5) 0.2707(4) 0.5938(5) 0.0477(17) Uani 1 1 d . . .
C30 C -0.0494(5) 0.8557(4) 0.2404(5) 0.0467(16) Uani 1 1 d . . .
C20 C 0.1729(5) 0.9631(4) 0.3712(4) 0.0461(16) Uani 1 1 d . . .
C4 C 0.4367(5) 0.1005(5) 0.5843(5) 0.0511(17) Uani 1 1 d . . .
C15 C 0.7878(5) 0.3030(4) 0.6651(4) 0.0474(16) Uani 1 1 d . . .
C10 C 0.8718(6) 0.3618(5) 0.6420(5) 0.0561(19) Uani 1 1 d . . .
C25 C -0.1368(6) 0.8048(4) 0.2668(5) 0.0517(17) Uani 1 1 d . . .
C14 C 0.7875(6) 0.2783(4) 0.7539(4) 0.0528(18) Uani 1 1 d . . .
H14 H 0.7344 0.2399 0.7692 0.063 Uiso 1 1 calc R . .
C26 C -0.2122(6) 0.7654(5) 0.1982(6) 0.066(2) Uani 1 1 d . . .
H26 H -0.2694 0.7316 0.2139 0.080 Uiso 1 1 calc R . .
C13 C 0.8656(6) 0.3107(5) 0.8190(5) 0.065(2) Uani 1 1 d . . .
H13 H 0.8654 0.2934 0.8784 0.078 Uiso 1 1 calc R . .
C21 C 0.0282(5) 0.8910(4) 0.3095(5) 0.0458(16) Uani 1 1 d . . .
C5 C 0.5708(6) 0.1939(5) 0.5286(5) 0.0557(18) Uani 1 1 d . . .
C9 C 0.8721(7) 0.3875(5) 0.5510(5) 0.069(2) Uani 1 1 d . . .
H9 H 0.9247 0.4273 0.5372 0.083 Uiso 1 1 calc R . .
C28 C -0.1178(6) 0.8293(5) 0.0852(5) 0.064(2) Uani 1 1 d . . .
H28 H -0.1140 0.8393 0.0247 0.077 Uiso 1 1 calc R . .
C29 C -0.0409(6) 0.8668(5) 0.1489(5) 0.0559(19) Uani 1 1 d . . .
H29 H 0.0164 0.8993 0.1314 0.067 Uiso 1 1 calc R . .
C24 C -0.1483(6) 0.7964(5) 0.3581(6) 0.067(2) Uani 1 1 d . . .
H24 H -0.2071 0.7648 0.3741 0.080 Uiso 1 1 calc R . .
C3 C 0.3211(6) 0.0169(5) 0.6454(5) 0.062(2) Uani 1 1 d . . .
H3 H 0.2635 -0.0227 0.6450 0.075 Uiso 1 1 calc R . .
C8 C 0.7957(6) 0.3546(5) 0.4816(5) 0.067(2) Uani 1 1 d . . .
H8 H 0.7984 0.3698 0.4220 0.080 Uiso 1 1 calc R . .
C11 C 0.9500(6) 0.3925(5) 0.7115(6) 0.063(2) Uani 1 1 d . . .
H11 H 1.0055 0.4293 0.6977 0.075 Uiso 1 1 calc R . .
C22 C 0.0136(6) 0.8793(4) 0.3982(5) 0.0514(17) Uani 1 1 d . . .
C2 C 0.3716(6) 0.0486(5) 0.7214(5) 0.0556(18) Uani 1 1 d . . .
C23 C -0.0747(6) 0.8336(5) 0.4243(5) 0.067(2) Uani 1 1 d . . .
H23 H -0.0835 0.8285 0.4845 0.080 Uiso 1 1 calc R . .
C7 C 0.7142(6) 0.2973(5) 0.5058(5) 0.059(2) Uani 1 1 d . . .
C12 C 0.9464(7) 0.3698(5) 0.7974(6) 0.067(2) Uani 1 1 d . . .
H12 H 0.9972 0.3931 0.8427 0.081 Uiso 1 1 calc R . .
C17 C 0.3808(6) 1.0904(5) 0.1764(5) 0.0584(19) Uani 1 1 d . . .
C1 C 0.3534(7) 0.0303(5) 0.8170(5) 0.074(2) Uani 1 1 d . . .
H1A H 0.2767 0.0287 0.8204 0.111 Uiso 1 1 calc R . .
H1B H 0.3867 0.0764 0.8555 0.111 Uiso 1 1 calc R . .
H1C H 0.3853 -0.0259 0.8358 0.111 Uiso 1 1 calc R . .
C27 C -0.2017(7) 0.7762(5) 0.1099(6) 0.076(2) Uani 1 1 d . . .
H27 H -0.2502 0.7484 0.0659 0.091 Uiso 1 1 calc R . .
C16 C 0.3991(7) 1.1050(6) 0.0803(5) 0.083(3) Uani 1 1 d . . .
H16A H 0.3560 1.1544 0.0557 0.125 Uiso 1 1 calc R . .
H16B H 0.3782 1.0527 0.0458 0.125 Uiso 1 1 calc R . .
H16C H 0.4746 1.1173 0.0784 0.125 Uiso 1 1 calc R . .
N6 N 0.1197(4) 0.9389(3) 0.2939(4) 0.0460(13) Uani 1 1 d . . .
N5 N 0.2673(4) 1.0123(4) 0.3831(4) 0.0489(14) Uani 1 1 d . . .
H5 H 0.2965 1.0241 0.4371 0.059 Uiso 1 1 calc R . .
N3 N 0.6268(4) 0.2143(4) 0.6059(3) 0.0484(14) Uani 1 1 d . . .
N2 N 0.4824(4) 0.1373(4) 0.5150(4) 0.0576(16) Uani 1 1 d . . .
H2 H 0.4549 0.1247 0.4608 0.069 Uiso 1 1 calc R . .
N4 N 0.4065(4) 1.0920(4) 0.3313(4) 0.0482(14) Uani 1 1 d . . .
N1 N 0.3556(5) 0.0437(4) 0.5663(4) 0.0594(16) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.737(7) . ?
S1 C2 1.747(7) . ?
S3 C19 1.736(6) . ?
S3 C17 1.737(8) . ?
S4 C22 1.739(7) . ?
S4 C20 1.756(7) . ?
S2 C7 1.738(7) . ?
S2 C5 1.752(7) . ?
C18 C17 1.339(9) . ?
C18 N4 1.378(8) . ?
C19 N4 1.338(8) . ?
C19 N5 1.341(8) . ?
C6 N3 1.361(8) . ?
C6 C7 1.392(9) . ?
C6 C15 1.432(9) . ?
C30 C29 1.404(9) . ?
C30 C21 1.419(9) . ?
C30 C25 1.428(9) . ?
C20 N6 1.307(8) . ?
C20 N5 1.377(8) . ?
C4 N1 1.321(8) . ?
C4 N2 1.370(8) . ?
C15 C14 1.387(9) . ?
C15 C10 1.444(9) . ?
C10 C11 1.403(9) . ?
C10 C9 1.423(10) . ?
C25 C24 1.406(10) . ?
C25 C26 1.423(9) . ?
C14 C13 1.369(9) . ?
C26 C27 1.361(11) . ?
C13 C12 1.411(10) . ?
C21 C22 1.381(9) . ?
C21 N6 1.391(8) . ?
C5 N3 1.306(8) . ?
C5 N2 1.382(8) . ?
C9 C8 1.401(10) . ?
C28 C29 1.377(9) . ?
C28 C27 1.403(11) . ?
C24 C23 1.374(10) . ?
C3 C2 1.315(9) . ?
C3 N1 1.377(9) . ?
C8 C7 1.414(10) . ?
C11 C12 1.342(10) . ?
C22 C23 1.396(9) . ?
C2 C1 1.510(10) . ?
C17 C16 1.509(10) . ?

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
C4 S1 C2 89.0(3) . . ?
C19 S3 C17 89.3(3) . . ?
C22 S4 C20 87.9(3) . . ?
C7 S2 C5 88.0(3) . . ?
C17 C18 N4 116.2(7) . . ?
N4 C19 N5 120.3(6) . . ?
N4 C19 S3 113.6(5) . . ?
N5 C19 S3 126.1(5) . . ?
N3 C6 C7 116.1(6) . . ?
N3 C6 C15 124.0(6) . . ?
C7 C6 C15 120.0(6) . . ?
C29 C30 C21 122.6(6) . . ?
C29 C30 C25 119.8(6) . . ?
C21 C30 C25 117.6(6) . . ?
N6 C20 N5 125.7(6) . . ?
N6 C20 S4 117.1(5) . . ?
N5 C20 S4 117.2(5) . . ?
N1 C4 N2 119.3(6) . . ?
N1 C4 S1 114.2(5) . . ?
N2 C4 S1 126.5(5) . . ?
C14 C15 C6 122.6(6) . . ?
C14 C15 C10 119.5(6) . . ?
C6 C15 C10 117.9(6) . . ?
C11 C10 C9 122.2(7) . . ?
C11 C10 C15 118.1(7) . . ?
C9 C10 C15 119.7(7) . . ?
C24 C25 C26 121.7(7) . . ?
C24 C25 C30 120.1(6) . . ?
C26 C25 C30 118.1(7) . . ?
C13 C14 C15 119.9(7) . . ?
C27 C26 C25 121.0(8) . . ?
C14 C13 C12 121.0(7) . . ?
C22 C21 N6 116.5(6) . . ?
C22 C21 C30 119.6(6) . . ?
N6 C21 C30 123.9(6) . . ?
N3 C5 N2 126.2(7) . . ?
N3 C5 S2 116.1(5) . . ?
N2 C5 S2 117.7(5) . . ?
C8 C9 C10 122.0(7) . . ?
C29 C28 C27 121.2(8) . . ?
C28 C29 C30 119.7(7) . . ?
C23 C24 C25 121.6(7) . . ?
C2 C3 N1 118.4(7) . . ?
C9 C8 C7 117.3(7) . . ?
C12 C11 C10 121.4(7) . . ?
C21 C22 C23 123.1(7) . . ?
C21 C22 S4 109.9(5) . . ?
C23 C22 S4 127.0(6) . . ?
C3 C2 C1 130.1(7) . . ?
C3 C2 S1 109.0(6) . . ?
C1 C2 S1 120.8(6) . . ?
C24 C23 C22 117.8(7) . . ?
C6 C7 C8 123.1(7) . . ?
C6 C7 S2 109.6(5) . . ?
C8 C7 S2 127.2(6) . . ?
C11 C12 C13 120.0(7) . . ?
C18 C17 C16 128.8(7) . . ?
C18 C17 S3 110.3(6) . . ?
C16 C17 S3 120.8(6) . . ?
C26 C27 C28 120.0(7) . . ?
C20 N6 C21 108.6(6) . . ?
C19 N5 C20 123.4(6) . . ?
C5 N3 C6 110.2(6) . . ?
C4 N2 C5 122.7(6) . . ?
C19 N4 C18 110.5(6) . . ?
C4 N1 C3 109.3(6) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.085






####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1453062'
_audit_update_record             
;
2016-02-12 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 N3 O S'
_chemical_formula_weight         283.34

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'
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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.079(5)
_cell_length_b                   9.344(6)
_cell_length_c                   9.702(6)
_cell_angle_alpha                100.825(13)
_cell_angle_beta                 94.448(13)
_cell_angle_gamma                105.221(12)
_cell_volume                     687.9(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1527
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      25.48

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            5716
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_sigmaI/netI    0.0598
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2461
_reflns_number_gt                1552
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0000P)²+0.1002P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2461
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.0793
_refine_ls_wR_factor_gt          0.0751
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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
S1 S 0.51971(8) 0.65862(8) 0.40212(6) 0.0613(2) Uani 1 1 d . . .
O1 O 0.3503(2) 0.54776(19) -0.11089(16) 0.0627(5) Uani 1 1 d . . .
N1 N 0.2942(3) 0.7699(2) 0.2948(2) 0.0590(6) Uani 1 1 d . . .
N2 N 0.3988(3) 0.6074(2) 0.1272(2) 0.0542(6) Uani 1 1 d . . .
N3 N 0.2047(3) 0.6999(2) 0.0061(2) 0.0525(5) Uani 1 1 d . . .
C1 C 0.4904(3) 0.8162(3) 0.6728(2) 0.0805(9) Uani 1 1 d . . .
H1A H 0.4400 0.8928 0.7163 0.121 Uiso 1 1 calc R . .
H1B H 0.6143 0.8541 0.6915 0.121 Uiso 1 1 calc R . .
H1C H 0.4526 0.7272 0.7109 0.121 Uiso 1 1 calc R . .
C2 C 0.4348(3) 0.7766(3) 0.5161(2) 0.0578(7) Uani 1 1 d . . .
C3 C 0.3213(3) 0.8224(3) 0.4397(3) 0.0661(8) Uani 1 1 d . . .
H3 H 0.2624 0.8878 0.4832 0.079 Uiso 1 1 calc R . .
C4 C 0.3921(3) 0.6826(3) 0.2619(2) 0.0487(6) Uani 1 1 d . . .
C5 C 0.3178(3) 0.6147(3) -0.0005(2) 0.0489(6) Uani 1 1 d . . .
C6 C 0.1168(3) 0.7223(3) -0.1172(2) 0.0469(6) Uani 1 1 d . . .
C7 C 0.0226(3) 0.6038(3) -0.2192(3) 0.0589(7) Uani 1 1 d . . .
H7 H 0.0143 0.5055 -0.2085 0.071 Uiso 1 1 calc R . .
C8 C -0.0634(3) 0.6261(3) -0.3416(3) 0.0692(8) Uani 1 1 d . . .
H8 H -0.1261 0.5431 -0.4120 0.083 Uiso 1 1 calc R . .
C9 C -0.0543(3) 0.7696(4) -0.3563(3) 0.0656(8) Uani 1 1 d . . .
H9 H -0.1122 0.7840 -0.4369 0.079 Uiso 1 1 calc R . .
C10 C 0.0406(3) 0.8959(3) -0.2524(2) 0.0518(6) Uani 1 1 d . . .
C15 C 0.1301(3) 0.8737(3) -0.1294(2) 0.0446(6) Uani 1 1 d . . .
C14 C 0.2288(3) 1.0011(3) -0.0281(3) 0.0553(7) Uani 1 1 d . . .
H14 H 0.2904 0.9881 0.0514 0.066 Uiso 1 1 calc R . .
C13 C 0.2358(4) 1.1447(3) -0.0448(3) 0.0725(8) Uani 1 1 d . . .
H13 H 0.3000 1.2285 0.0240 0.087 Uiso 1 1 calc R . .
C12 C 0.1467(4) 1.1652(4) -0.1650(4) 0.0784(9) Uani 1 1 d . . .
H12 H 0.1528 1.2632 -0.1758 0.094 Uiso 1 1 calc R . .
C11 C 0.0526(3) 1.0465(4) -0.2649(3) 0.0698(8) Uani 1 1 d . . .
H11 H -0.0060 1.0633 -0.3440 0.084 Uiso 1 1 calc R . .
H3A H 0.197(3) 0.750(2) 0.089(2) 0.044(7) Uiso 1 1 d . . .
H2 H 0.466(3) 0.561(3) 0.115(2) 0.057(8) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.722(3) . ?
S1 C4 1.727(2) . ?
O1 C5 1.219(3) . ?
N1 C4 1.294(3) . ?
N1 C3 1.380(3) . ?
N2 C4 1.374(3) . ?
N2 C5 1.378(3) . ?
N2 H2 0.78(2) . ?
N3 C5 1.358(3) . ?
N3 C6 1.421(3) . ?
N3 H3A 0.865(19) . ?
C1 C2 1.499(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.338(3) . ?
C3 H3 0.9300 . ?
C6 C7 1.346(3) . ?
C6 C15 1.419(3) . ?
C7 C8 1.406(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.358(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.398(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.414(3) . ?
C10 C15 1.425(3) . ?
C15 C14 1.399(3) . ?
C14 C13 1.368(3) . ?
C14 H14 0.9300 . ?
C13 C12 1.393(4) . ?
C13 H13 0.9300 . ?
C12 C11 1.337(4) . ?
C12 H12 0.9300 . ?
C11 H11 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
C2 S1 C4 89.23(12) . . ?
C4 N1 C3 108.51(19) . . ?
C4 N2 C5 129.6(2) . . ?
C4 N2 H2 119.2(17) . . ?
C5 N2 H2 110.6(17) . . ?
C5 N3 C6 122.3(2) . . ?
C5 N3 H3A 117.1(14) . . ?
C6 N3 H3A 120.2(14) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 129.6(2) . . ?
C3 C2 S1 108.43(19) . . ?
C1 C2 S1 122.01(19) . . ?
C2 C3 N1 118.1(2) . . ?
C2 C3 H3 120.9 . . ?
N1 C3 H3 120.9 . . ?
N1 C4 N2 125.4(2) . . ?
N1 C4 S1 115.68(18) . . ?
N2 C4 S1 118.93(18) . . ?
O1 C5 N3 123.8(2) . . ?
O1 C5 N2 120.0(2) . . ?
N3 C5 N2 116.2(2) . . ?
C7 C6 C15 120.8(2) . . ?
C7 C6 N3 121.3(2) . . ?
C15 C6 N3 117.9(2) . . ?
C6 C7 C8 121.3(3) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 119.5(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 121.2(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C9 C10 C11 122.5(2) . . ?
C9 C10 C15 119.4(2) . . ?
C11 C10 C15 118.2(2) . . ?
C14 C15 C6 123.3(2) . . ?
C14 C15 C10 118.9(2) . . ?
C6 C15 C10 117.9(2) . . ?
C13 C14 C15 120.7(2) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C11 C12 C13 121.1(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?

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
C4 S1 C2 C3 -0.2(2) . . . . ?
C4 S1 C2 C1 -179.2(2) . . . . ?
C1 C2 C3 N1 179.3(3) . . . . ?
S1 C2 C3 N1 0.4(3) . . . . ?
C4 N1 C3 C2 -0.4(3) . . . . ?
C3 N1 C4 N2 179.0(2) . . . . ?
C3 N1 C4 S1 0.3(3) . . . . ?
C5 N2 C4 N1 5.3(4) . . . . ?
C5 N2 C4 S1 -176.0(2) . . . . ?
C2 S1 C4 N1 -0.1(2) . . . . ?
C2 S1 C4 N2 -178.9(2) . . . . ?
C6 N3 C5 O1 -1.9(4) . . . . ?
C6 N3 C5 N2 177.6(2) . . . . ?
C4 N2 C5 O1 174.3(2) . . . . ?
C4 N2 C5 N3 -5.2(4) . . . . ?
C5 N3 C6 C7 54.4(3) . . . . ?
C5 N3 C6 C15 -126.0(2) . . . . ?
C15 C6 C7 C8 0.9(4) . . . . ?
N3 C6 C7 C8 -179.6(2) . . . . ?
C6 C7 C8 C9 -1.3(4) . . . . ?
C7 C8 C9 C10 0.6(4) . . . . ?
C8 C9 C10 C11 179.9(2) . . . . ?
C8 C9 C10 C15 0.4(4) . . . . ?
C7 C6 C15 C14 -178.7(2) . . . . ?
N3 C6 C15 C14 1.7(3) . . . . ?
C7 C6 C15 C10 0.1(3) . . . . ?
N3 C6 C15 C10 -179.4(2) . . . . ?
C9 C10 C15 C14 178.1(2) . . . . ?
C11 C10 C15 C14 -1.4(3) . . . . ?
C9 C10 C15 C6 -0.8(3) . . . . ?
C11 C10 C15 C6 179.7(2) . . . . ?
C6 C15 C14 C13 -179.4(2) . . . . ?
C10 C15 C14 C13 1.7(3) . . . . ?
C15 C14 C13 C12 -1.2(4) . . . . ?
C14 C13 C12 C11 0.5(4) . . . . ?
C13 C12 C11 C10 -0.2(4) . . . . ?
C9 C10 C11 C12 -178.8(3) . . . . ?
C15 C10 C11 C12 0.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 1453063'
_audit_update_record             
;
2016-02-12 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 Cl N3 O2 S'
_chemical_formula_weight         337.82

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'
Cl Cl 0.1484 0.1585 '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   Pbca

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

_cell_length_a                   15.4084(8)
_cell_length_b                   7.7845(4)
_cell_length_c                   27.4631(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3294.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5994
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      19.16

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408
_exptl_absorpt_coefficient_mu    0.368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            27785
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2999
_reflns_number_gt                1639
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0000P)²+1.4000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2999
_refine_ls_number_parameters     216
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0654
_refine_ls_wR_factor_gt          0.0578
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.280
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.50364(5) 0.03051(12) 0.87444(3) 0.0665(3) Uani 1 1 d . . .
O1 O 0.65110(12) 0.0880(3) 0.82780(7) 0.0700(6) Uani 1 1 d . . .
N2 N 0.66606(15) -0.0937(3) 0.89204(8) 0.0520(7) Uani 1 1 d . . .
N1 N 0.55103(15) -0.1511(3) 0.94533(8) 0.0628(7) Uani 1 1 d . . .
H1 H 0.5824 -0.2099 0.9652 0.075 Uiso 1 1 calc R . .
N3 N 0.78533(15) -0.0219(3) 0.84650(8) 0.0556(7) Uani 1 1 d D . .
C7 C 0.80189(19) 0.1134(4) 0.76756(10) 0.0684(9) Uani 1 1 d . . .
H7 H 0.7431 0.0972 0.7615 0.082 Uiso 1 1 calc R . .
C8 C 0.8542(2) 0.1958(5) 0.73275(11) 0.0804(11) Uani 1 1 d . . .
H8 H 0.8293 0.2358 0.7040 0.096 Uiso 1 1 calc R . .
C9 C 0.9400(2) 0.2179(4) 0.74039(11) 0.0746(10) Uani 1 1 d . . .
H9 H 0.9734 0.2733 0.7169 0.089 Uiso 1 1 calc R . .
C10 C 0.97966(18) 0.1583(4) 0.78325(11) 0.0599(9) Uani 1 1 d . . .
C15 C 0.92769(17) 0.0760(4) 0.81948(10) 0.0518(8) Uani 1 1 d . . .
C6 C 0.83695(17) 0.0571(4) 0.81006(10) 0.0524(8) Uani 1 1 d . . .
C14 C 0.96904(18) 0.0170(4) 0.86244(10) 0.0629(9) Uani 1 1 d . . .
H14 H 0.9363 -0.0367 0.8865 0.076 Uiso 1 1 calc R . .
C13 C 1.05681(19) 0.0380(4) 0.86900(12) 0.0768(10) Uani 1 1 d . . .
H13 H 1.0831 -0.0018 0.8973 0.092 Uiso 1 1 calc R . .
C12 C 1.1069(2) 0.1197(5) 0.83304(14) 0.0851(12) Uani 1 1 d . . .
H12 H 1.1662 0.1336 0.8377 0.102 Uiso 1 1 calc R . .
C11 C 1.0695(2) 0.1783(5) 0.79169(13) 0.0790(10) Uani 1 1 d . . .
H11 H 1.1035 0.2328 0.7684 0.095 Uiso 1 1 calc R . .
C5 C 0.69860(18) 0.0002(4) 0.85241(10) 0.0533(8) Uani 1 1 d . . .
C4 C 0.58198(17) -0.0782(4) 0.90541(9) 0.0512(8) Uani 1 1 d . . .
C3 C 0.4626(2) -0.1229(4) 0.95199(12) 0.0722(10) Uani 1 1 d . . .
H3 H 0.4318 -0.1664 0.9783 0.087 Uiso 1 1 calc R . .
C2 C 0.42642(19) -0.0287(5) 0.91746(11) 0.0696(10) Uani 1 1 d . . .
C1 C 0.33310(18) 0.0238(5) 0.91207(12) 0.1032(13) Uani 1 1 d . . .
H1A H 0.3000 -0.0214 0.9388 0.155 Uiso 1 1 calc R . .
H1B H 0.3106 -0.0206 0.8820 0.155 Uiso 1 1 calc R . .
H1C H 0.3291 0.1468 0.9120 0.155 Uiso 1 1 calc R . .
Cl1 Cl 0.17625(5) 0.21778(11) 0.04458(3) 0.0770(3) Uani 1 1 d . . .
O2 O 0.6528(2) 0.6444(5) 0.00325(10) 0.0946(9) Uani 1 1 d . . .
H2 H 0.7036(13) -0.141(3) 0.9123(8) 0.045(8) Uiso 1 1 d . . .
H3A H 0.8115(14) -0.088(3) 0.8691(7) 0.065(9) Uiso 1 1 d D . .
H2P H 0.647(3) 0.545(6) -0.0075(16) 0.16(3) Uiso 1 1 d . . .
H2Q H 0.708(3) 0.684(7) -0.0058(17) 0.21(3) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.702(3) . ?
S1 C2 1.739(3) . ?
O1 C5 1.208(3) . ?
N2 C4 1.352(3) . ?
N2 C5 1.403(3) . ?
N2 H2 0.88(2) . ?
N1 C4 1.323(3) . ?
N1 C3 1.392(3) . ?
N1 H1 0.8600 . ?
N3 C5 1.357(3) . ?
N3 C6 1.419(3) . ?
N3 H3A 0.903(7) . ?
C7 C6 1.359(3) . ?
C7 C8 1.405(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.350(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.405(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.412(4) . ?
C10 C15 1.429(3) . ?
C15 C14 1.417(3) . ?
C15 C6 1.429(3) . ?
C14 C13 1.374(4) . ?
C14 H14 0.9300 . ?
C13 C12 1.405(4) . ?
C13 H13 0.9300 . ?
C12 C11 1.353(4) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C3 C2 1.322(4) . ?
C3 H3 0.9300 . ?
C2 C1 1.502(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
O2 H2P 0.83(5) . ?
O2 H2Q 0.94(4) . ?

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
C4 S1 C2 90.80(15) . . ?
C4 N2 C5 120.4(3) . . ?
C4 N2 H2 119.6(14) . . ?
C5 N2 H2 118.1(15) . . ?
C4 N1 C3 113.2(3) . . ?
C4 N1 H1 123.4 . . ?
C3 N1 H1 123.4 . . ?
C5 N3 C6 125.6(3) . . ?
C5 N3 H3A 115.5(16) . . ?
C6 N3 H3A 118.9(16) . . ?
C6 C7 C8 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 120.9(3) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 120.9(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C11 121.8(3) . . ?
C9 C10 C15 119.2(3) . . ?
C11 C10 C15 119.0(3) . . ?
C14 C15 C10 118.2(3) . . ?
C14 C15 C6 123.8(3) . . ?
C10 C15 C6 117.9(3) . . ?
C7 C6 N3 121.5(3) . . ?
C7 C6 C15 120.8(3) . . ?
N3 C6 C15 117.7(2) . . ?
C13 C14 C15 120.9(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
O1 C5 N3 127.0(3) . . ?
O1 C5 N2 120.8(3) . . ?
N3 C5 N2 112.2(3) . . ?
N1 C4 N2 122.2(3) . . ?
N1 C4 S1 111.8(2) . . ?
N2 C4 S1 126.0(2) . . ?
C2 C3 N1 114.0(3) . . ?
C2 C3 H3 123.0 . . ?
N1 C3 H3 123.0 . . ?
C3 C2 C1 128.7(3) . . ?
C3 C2 S1 110.2(2) . . ?
C1 C2 S1 121.1(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
H2P O2 H2Q 108(4) . . ?

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 C7 C8 C9 1.2(5) . . . . ?
C7 C8 C9 C10 0.3(5) . . . . ?
C8 C9 C10 C11 179.3(3) . . . . ?
C8 C9 C10 C15 -1.1(5) . . . . ?
C9 C10 C15 C14 -180.0(3) . . . . ?
C11 C10 C15 C14 -0.3(4) . . . . ?
C9 C10 C15 C6 0.4(4) . . . . ?
C11 C10 C15 C6 -179.9(3) . . . . ?
C8 C7 C6 N3 178.1(3) . . . . ?
C8 C7 C6 C15 -1.9(5) . . . . ?
C5 N3 C6 C7 -24.0(5) . . . . ?
C5 N3 C6 C15 156.0(3) . . . . ?
C14 C15 C6 C7 -178.5(3) . . . . ?
C10 C15 C6 C7 1.1(4) . . . . ?
C14 C15 C6 N3 1.5(4) . . . . ?
C10 C15 C6 N3 -178.9(2) . . . . ?
C10 C15 C14 C13 -0.1(4) . . . . ?
C6 C15 C14 C13 179.5(3) . . . . ?
C15 C14 C13 C12 0.3(5) . . . . ?
C14 C13 C12 C11 0.0(5) . . . . ?
C13 C12 C11 C10 -0.5(5) . . . . ?
C9 C10 C11 C12 -179.7(3) . . . . ?
C15 C10 C11 C12 0.6(5) . . . . ?
C6 N3 C5 O1 0.8(5) . . . . ?
C6 N3 C5 N2 -179.3(2) . . . . ?
C4 N2 C5 O1 -4.5(4) . . . . ?
C4 N2 C5 N3 175.6(2) . . . . ?
C3 N1 C4 N2 -178.7(3) . . . . ?
C3 N1 C4 S1 0.6(3) . . . . ?
C5 N2 C4 N1 -173.2(3) . . . . ?
C5 N2 C4 S1 7.7(4) . . . . ?
C2 S1 C4 N1 -0.6(2) . . . . ?
C2 S1 C4 N2 178.6(3) . . . . ?
C4 N1 C3 C2 -0.2(4) . . . . ?
N1 C3 C2 C1 178.5(3) . . . . ?
N1 C3 C2 S1 -0.3(4) . . . . ?
C4 S1 C2 C3 0.5(3) . . . . ?
C4 S1 C2 C1 -178.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1453064'
_audit_update_record             
;
2016-02-12 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 Cl N3 O6 S'
_chemical_formula_weight         401.82

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'
Cl Cl 0.1484 0.1585 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21'

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

_cell_length_a                   8.3350(16)
_cell_length_b                   7.3210(18)
_cell_length_c                   14.859(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.577(13)
_cell_angle_gamma                90.00
_cell_volume                     906.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    741
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      20.05

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_process_details   multi-scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            5144
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_sigmaI/netI    0.1197
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2731
_reflns_number_gt                1889
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0000P)²+0.9001P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_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   0.48(17)
_refine_ls_number_reflns         2731
_refine_ls_number_parameters     249
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1797
_refine_ls_wR_factor_gt          0.1456
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.0506(2) 1.4129(3) 0.32712(12) 0.0607(5) Uani 1 1 d . . .
O1 O 0.0791(6) 1.0974(8) 0.3734(4) 0.0734(15) Uani 1 1 d . . .
N1 N 0.0206(6) 1.4438(9) 0.1644(4) 0.0614(16) Uani 1 1 d . . .
H1 H 0.0591 1.4221 0.1124 0.074 Uiso 1 1 calc R . .
N2 N 0.1253(7) 1.1737(8) 0.2289(4) 0.0539(14) Uani 1 1 d . . .
N3 N 0.2345(6) 0.9089(9) 0.2862(4) 0.0583(14) Uani 1 1 d . . .
H3A H 0.2767 0.9026 0.2341 0.070 Uiso 1 1 calc R . .
C6 C 0.2670(8) 0.7644(11) 0.3459(5) 0.0564(18) Uani 1 1 d . . .
C7 C 0.2203(9) 0.7618(11) 0.4341(5) 0.0626(19) Uani 1 1 d . . .
H7 H 0.1647 0.8611 0.4567 0.075 Uiso 1 1 calc R . .
C8 C 0.2546(9) 0.6148(12) 0.4898(5) 0.067(2) Uani 1 1 d . . .
H8 H 0.2195 0.6161 0.5487 0.080 Uiso 1 1 calc R . .
C9 C 0.3390(8) 0.4677(12) 0.4600(5) 0.068(2) Uani 1 1 d . . .
H9 H 0.3618 0.3711 0.4989 0.081 Uiso 1 1 calc R . .
C10 C 0.3925(8) 0.4613(10) 0.3693(5) 0.0561(18) Uani 1 1 d . . .
C15 C 0.3560(7) 0.6094(10) 0.3120(4) 0.0531(18) Uani 1 1 d . . .
C14 C 0.4070(8) 0.5978(13) 0.2219(5) 0.065(2) Uani 1 1 d . . .
H14 H 0.3844 0.6935 0.1824 0.078 Uiso 1 1 calc R . .
C13 C 0.4893(8) 0.4476(12) 0.1918(5) 0.067(2) Uani 1 1 d . . .
H13 H 0.5199 0.4413 0.1322 0.081 Uiso 1 1 calc R . .
C12 C 0.5261(9) 0.3071(14) 0.2502(6) 0.074(2) Uani 1 1 d . . .
H12 H 0.5851 0.2080 0.2302 0.089 Uiso 1 1 calc R . .
C11 C 0.4776(8) 0.3110(12) 0.3368(6) 0.068(2) Uani 1 1 d . . .
H11 H 0.5011 0.2130 0.3748 0.081 Uiso 1 1 calc R . .
C5 C 0.1415(8) 1.0604(12) 0.3030(5) 0.0591(18) Uani 1 1 d . . .
C4 C 0.0406(8) 1.3314(11) 0.2336(5) 0.0559(18) Uani 1 1 d . . .
C2 C -0.1130(8) 1.6065(11) 0.2676(5) 0.062(2) Uani 1 1 d . . .
C3 C -0.0684(8) 1.6009(11) 0.1831(5) 0.0633(19) Uani 1 1 d . . .
H3 H -0.0931 1.6910 0.1408 0.076 Uiso 1 1 calc R . .
C1 C -0.2059(9) 1.7539(13) 0.3154(6) 0.079(2) Uani 1 1 d . . .
H1A H -0.2126 1.8610 0.2782 0.118 Uiso 1 1 calc R . .
H1B H -0.1518 1.7835 0.3714 0.118 Uiso 1 1 calc R . .
H1C H -0.3121 1.7105 0.3269 0.118 Uiso 1 1 calc R . .
Cl1 Cl 0.7677(2) 0.0613(3) 0.04222(12) 0.0679(6) Uani 1 1 d . . .
O3 O 0.8004(7) 0.0434(10) 0.1345(3) 0.099(2) Uani 1 1 d . . .
O4 O 0.7838(8) -0.1027(10) -0.0059(4) 0.0999(19) Uani 1 1 d . . .
O2 O 0.6057(7) 0.1257(11) 0.0273(5) 0.113(3) Uani 1 1 d . . .
O5 O 0.8756(9) 0.1891(11) 0.0045(5) 0.122(3) Uani 1 1 d . . .
O6 O 0.2954(9) -0.0008(9) 0.0940(4) 0.0896(19) Uani 1 1 d D . .
H2 H 0.169(5) 1.155(7) 0.176(4) 0.016(13) Uiso 1 1 d . . .
H6P H 0.355(13) 0.103(10) 0.080(8) 0.14(5) Uiso 1 1 d D . .
H6Q H 0.251(10) -0.081(11) 0.052(5) 0.11(3) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.710(7) . ?
S1 C2 1.743(8) . ?
O1 C5 1.211(8) . ?
N1 C4 1.323(9) . ?
N1 C3 1.401(9) . ?
N1 H1 0.8600 . ?
N2 C4 1.357(9) . ?
N2 C5 1.382(9) . ?
N2 H2 0.88(5) . ?
N3 C5 1.379(10) . ?
N3 C6 1.402(9) . ?
N3 H3A 0.8600 . ?
C6 C7 1.378(9) . ?
C6 C15 1.454(10) . ?
C7 C8 1.383(11) . ?
C7 H7 0.9300 . ?
C8 C9 1.367(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.432(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.402(10) . ?
C10 C15 1.407(10) . ?
C15 C14 1.417(9) . ?
C14 C13 1.377(11) . ?
C14 H14 0.9300 . ?
C13 C12 1.375(11) . ?
C13 H13 0.9300 . ?
C12 C11 1.359(11) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C2 C3 1.319(10) . ?
C2 C1 1.516(11) . ?
C3 H3 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
Cl1 O3 1.397(5) . ?
Cl1 O4 1.406(7) . ?
Cl1 O5 1.424(7) . ?
Cl1 O2 1.441(6) . ?
O6 H6P 0.93(2) . ?
O6 H6Q 0.93(2) . ?

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
C4 S1 C2 90.2(4) . . ?
C4 N1 C3 114.4(6) . . ?
C4 N1 H1 122.8 . . ?
C3 N1 H1 122.8 . . ?
C4 N2 C5 120.7(7) . . ?
C4 N2 H2 114(3) . . ?
C5 N2 H2 125(3) . . ?
C5 N3 C6 126.3(6) . . ?
C5 N3 H3A 116.8 . . ?
C6 N3 H3A 116.8 . . ?
C7 C6 N3 123.9(7) . . ?
C7 C6 C15 118.6(7) . . ?
N3 C6 C15 117.5(6) . . ?
C6 C7 C8 121.4(8) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 121.2(7) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 120.5(7) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C15 119.9(7) . . ?
C11 C10 C9 121.6(7) . . ?
C15 C10 C9 118.5(7) . . ?
C10 C15 C14 117.4(7) . . ?
C10 C15 C6 119.7(6) . . ?
C14 C15 C6 122.9(7) . . ?
C13 C14 C15 121.3(8) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C12 C13 C14 119.8(7) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C11 C12 C13 121.0(8) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C11 C10 120.6(8) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
O1 C5 N3 126.3(7) . . ?
O1 C5 N2 121.3(8) . . ?
N3 C5 N2 112.4(6) . . ?
N1 C4 N2 123.0(6) . . ?
N1 C4 S1 111.4(6) . . ?
N2 C4 S1 125.6(6) . . ?
C3 C2 C1 129.0(8) . . ?
C3 C2 S1 111.7(6) . . ?
C1 C2 S1 119.3(6) . . ?
C2 C3 N1 112.3(7) . . ?
C2 C3 H3 123.9 . . ?
N1 C3 H3 123.9 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O3 Cl1 O4 113.6(4) . . ?
O3 Cl1 O5 109.9(4) . . ?
O4 Cl1 O5 106.9(4) . . ?
O3 Cl1 O2 109.8(4) . . ?
O4 Cl1 O2 107.7(4) . . ?
O5 Cl1 O2 108.9(5) . . ?
H6P O6 H6Q 125(10) . . ?

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
C5 N3 C6 C7 -5.9(10) . . . . ?
C5 N3 C6 C15 174.5(6) . . . . ?
N3 C6 C7 C8 179.5(6) . . . . ?
C15 C6 C7 C8 -0.9(10) . . . . ?
C6 C7 C8 C9 1.4(11) . . . . ?
C7 C8 C9 C10 -0.9(11) . . . . ?
C8 C9 C10 C11 -179.2(7) . . . . ?
C8 C9 C10 C15 0.0(10) . . . . ?
C11 C10 C15 C14 0.6(9) . . . . ?
C9 C10 C15 C14 -178.6(6) . . . . ?
C11 C10 C15 C6 179.6(6) . . . . ?
C9 C10 C15 C6 0.4(9) . . . . ?
C7 C6 C15 C10 0.0(9) . . . . ?
N3 C6 C15 C10 179.6(6) . . . . ?
C7 C6 C15 C14 179.0(6) . . . . ?
N3 C6 C15 C14 -1.4(9) . . . . ?
C10 C15 C14 C13 -0.1(10) . . . . ?
C6 C15 C14 C13 -179.1(6) . . . . ?
C15 C14 C13 C12 -1.3(11) . . . . ?
C14 C13 C12 C11 2.3(12) . . . . ?
C13 C12 C11 C10 -1.8(11) . . . . ?
C15 C10 C11 C12 0.3(10) . . . . ?
C9 C10 C11 C12 179.5(7) . . . . ?
C6 N3 C5 O1 3.8(11) . . . . ?
C6 N3 C5 N2 -176.7(5) . . . . ?
C4 N2 C5 O1 0.9(9) . . . . ?
C4 N2 C5 N3 -178.6(5) . . . . ?
C3 N1 C4 N2 -179.0(6) . . . . ?
C3 N1 C4 S1 0.2(7) . . . . ?
C5 N2 C4 N1 -179.5(6) . . . . ?
C5 N2 C4 S1 1.5(9) . . . . ?
C2 S1 C4 N1 -0.9(5) . . . . ?
C2 S1 C4 N2 178.3(6) . . . . ?
C4 S1 C2 C3 1.4(6) . . . . ?
C4 S1 C2 C1 -178.3(6) . . . . ?
C1 C2 C3 N1 178.1(7) . . . . ?
S1 C2 C3 N1 -1.6(8) . . . . ?
C4 N1 C3 C2 0.9(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.054



####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 1453065'
_audit_update_record             
;
2016-02-12 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H49 Cl N4 O S'
_chemical_formula_weight         561.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   8.3706(12)
_cell_length_b                   18.536(2)
_cell_length_c                   21.658(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.199(10)
_cell_angle_gamma                90.00
_cell_volume                     3317.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2873
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      18.57

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_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            34811
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         25.25
_reflns_number_total             5996
_reflns_number_gt                3181
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0500P)²+0.7731P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5996
_refine_ls_number_parameters     356
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1531
_refine_ls_wR_factor_gt          0.1330
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.200
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.81159(16) 0.44340(6) 0.38140(5) 0.1011(4) Uani 1 1 d . . .
O1 O 0.8593(3) 0.35913(13) 0.28261(12) 0.0919(8) Uani 1 1 d . . .
N1 N 0.7595(4) 0.56706(17) 0.32757(18) 0.0914(10) Uani 1 1 d . . .
N2 N 0.8084(4) 0.47685(18) 0.25811(19) 0.0776(10) Uani 1 1 d . . .
N3 N 0.8333(4) 0.39554(18) 0.18035(17) 0.0738(9) Uani 1 1 d . . .
C9 C 0.8667(6) 0.1913(2) 0.0995(2) 0.0960(13) Uani 1 1 d . . .
H9 H 0.8733 0.1455 0.0826 0.115 Uiso 1 1 calc R . .
C8 C 0.9625(5) 0.2080(2) 0.1536(2) 0.0904(12) Uani 1 1 d . . .
H8 H 1.0354 0.1741 0.1732 0.108 Uiso 1 1 calc R . .
C7 C 0.9531(4) 0.2767(2) 0.18061(18) 0.0780(11) Uani 1 1 d . . .
H7 H 1.0200 0.2878 0.2179 0.094 Uiso 1 1 calc R . .
C6 C 0.8457(4) 0.32766(19) 0.15233(18) 0.0672(9) Uani 1 1 d . . .
C15 C 0.7459(4) 0.3118(2) 0.09347(18) 0.0682(9) Uani 1 1 d . . .
C10 C 0.7564(5) 0.2417(2) 0.0681(2) 0.0803(11) Uani 1 1 d . . .
C11 C 0.6552(6) 0.2259(3) 0.0115(2) 0.1035(14) Uani 1 1 d . . .
H11 H 0.6599 0.1800 -0.0055 0.124 Uiso 1 1 calc R . .
C12 C 0.5507(6) 0.2747(3) -0.0197(2) 0.1046(14) Uani 1 1 d . . .
H12 H 0.4859 0.2621 -0.0571 0.126 Uiso 1 1 calc R . .
C13 C 0.5417(5) 0.3437(3) 0.0049(2) 0.0912(12) Uani 1 1 d . . .
H13 H 0.4707 0.3774 -0.0161 0.109 Uiso 1 1 calc R . .
C14 C 0.6372(4) 0.3621(2) 0.06023(18) 0.0779(10) Uani 1 1 d . . .
H14 H 0.6305 0.4084 0.0761 0.093 Uiso 1 1 calc R . .
C5 C 0.8351(4) 0.4058(2) 0.2427(2) 0.0720(10) Uani 1 1 d . . .
C4 C 0.7932(4) 0.5000(2) 0.31710(19) 0.0729(10) Uani 1 1 d . . .
C3 C 0.7465(5) 0.5745(2) 0.3905(3) 0.1033(14) Uani 1 1 d . . .
H3 H 0.7226 0.6188 0.4068 0.124 Uiso 1 1 calc R . .
C2 C 0.7696(6) 0.5158(2) 0.4267(2) 0.1008(13) Uani 1 1 d . . .
C1 C 0.7577(7) 0.5078(3) 0.4954(2) 0.145(2) Uani 1 1 d . . .
H1A H 0.7478 0.5546 0.5134 0.218 Uiso 1 1 calc R . .
H1B H 0.8534 0.4844 0.5166 0.218 Uiso 1 1 calc R . .
H1C H 0.6645 0.4792 0.4998 0.218 Uiso 1 1 calc R . .
N4 N 0.7472(3) 0.11269(14) 0.31484(12) 0.0623(7) Uani 1 1 d . . .
C19 C 0.7769(4) 0.06727(19) 0.25900(17) 0.0767(10) Uani 1 1 d . . .
H19A H 0.7920 0.0998 0.2253 0.092 Uiso 1 1 calc R . .
H19B H 0.8776 0.0412 0.2709 0.092 Uiso 1 1 calc R . .
C18 C 0.6474(5) 0.0135(2) 0.2336(2) 0.1091(15) Uani 1 1 d . . .
H18A H 0.5461 0.0377 0.2183 0.131 Uiso 1 1 calc R . .
H18B H 0.6298 -0.0209 0.2656 0.131 Uiso 1 1 calc R . .
C17 C 0.7180(9) -0.0267(4) 0.1766(4) 0.207(4) Uani 1 1 d D . .
H17A H 0.7222 0.0081 0.1434 0.248 Uiso 1 1 calc R . .
H17B H 0.8280 -0.0421 0.1918 0.248 Uiso 1 1 calc R . .
C16 C 0.6272(12) -0.0878(4) 0.1507(4) 0.290(5) Uani 1 1 d D . .
H16A H 0.5672 -0.1073 0.1811 0.435 Uiso 1 1 calc R . .
H16B H 0.6996 -0.1238 0.1395 0.435 Uiso 1 1 calc R . .
H16C H 0.5536 -0.0733 0.1142 0.435 Uiso 1 1 calc RD . .
C28 C 0.5950(4) 0.15827(18) 0.29903(17) 0.0723(10) Uani 1 1 d . . .
H28A H 0.5032 0.1258 0.2905 0.087 Uiso 1 1 calc R . .
H28B H 0.5822 0.1860 0.3359 0.087 Uiso 1 1 calc R . .
C29 C 0.5865(4) 0.20979(19) 0.24488(18) 0.0790(11) Uani 1 1 d . . .
H29A H 0.5969 0.1833 0.2071 0.095 Uiso 1 1 calc R . .
H29B H 0.6751 0.2440 0.2528 0.095 Uiso 1 1 calc R . .
C30 C 0.4263(4) 0.2498(2) 0.2361(2) 0.0905(12) Uani 1 1 d . . .
H30A H 0.3391 0.2149 0.2286 0.109 Uiso 1 1 calc R . .
H30B H 0.4168 0.2752 0.2744 0.109 Uiso 1 1 calc R . .
C31 C 0.4063(5) 0.3030(2) 0.1831(2) 0.1174(16) Uani 1 1 d . . .
H31A H 0.4888 0.3393 0.1910 0.176 Uiso 1 1 calc R . .
H31B H 0.3017 0.3253 0.1795 0.176 Uiso 1 1 calc R . .
H31C H 0.4155 0.2784 0.1448 0.176 Uiso 1 1 calc R . .
C20 C 0.8981(4) 0.15890(18) 0.33232(16) 0.0670(9) Uani 1 1 d . . .
H20A H 0.9905 0.1268 0.3407 0.080 Uiso 1 1 calc R . .
H20B H 0.9116 0.1876 0.2961 0.080 Uiso 1 1 calc R . .
C21 C 0.9038(4) 0.20954(18) 0.38768(17) 0.0757(10) Uani 1 1 d . . .
H21A H 0.8192 0.2455 0.3788 0.091 Uiso 1 1 calc R . .
H21B H 0.8858 0.1826 0.4243 0.091 Uiso 1 1 calc R . .
C22 C 1.0678(5) 0.2462(2) 0.40029(19) 0.0882(12) Uani 1 1 d . . .
H22A H 1.0795 0.2770 0.3650 0.106 Uiso 1 1 calc R . .
H22B H 1.1517 0.2097 0.4036 0.106 Uiso 1 1 calc R . .
C23 C 1.0920(5) 0.2917(2) 0.4598(2) 0.1129(15) Uani 1 1 d . . .
H23A H 1.0141 0.3300 0.4557 0.169 Uiso 1 1 calc R . .
H23B H 1.1992 0.3116 0.4664 0.169 Uiso 1 1 calc R . .
H23C H 1.0781 0.2618 0.4948 0.169 Uiso 1 1 calc R . .
C27 C 0.7177(4) 0.06465(18) 0.36918(17) 0.0706(10) Uani 1 1 d . . .
H27A H 0.7116 0.0954 0.4050 0.085 Uiso 1 1 calc R . .
H27B H 0.6127 0.0419 0.3578 0.085 Uiso 1 1 calc R . .
C26 C 0.8415(4) 0.00582(18) 0.38950(16) 0.0697(9) Uani 1 1 d . . .
H26A H 0.8496 -0.0261 0.3546 0.084 Uiso 1 1 calc R . .
H26B H 0.9469 0.0272 0.4033 0.084 Uiso 1 1 calc R . .
C25 C 0.7884(4) -0.03657(19) 0.44267(18) 0.0828(11) Uani 1 1 d . . .
H25A H 0.7880 -0.0045 0.4780 0.099 Uiso 1 1 calc R . .
H25B H 0.6783 -0.0531 0.4295 0.099 Uiso 1 1 calc R . .
C24 C 0.8937(5) -0.10092(19) 0.46378(18) 0.0924(12) Uani 1 1 d . . .
H24A H 0.8866 -0.1353 0.4303 0.139 Uiso 1 1 calc R . .
H24B H 0.8574 -0.1229 0.4992 0.139 Uiso 1 1 calc R . .
H24C H 1.0039 -0.0855 0.4752 0.139 Uiso 1 1 calc R . .
Cl1 Cl 0.28067(10) 0.05405(5) 0.37152(4) 0.0781(3) Uani 1 1 d . . .
H2 H 0.791(4) 0.5051(19) 0.2301(17) 0.079(14) Uiso 1 1 d . . .
H3A H 0.801(4) 0.4292(17) 0.1581(15) 0.060(11) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.730(4) . ?
S1 C2 1.732(4) . ?
O1 C5 1.216(4) . ?
N1 C4 1.303(4) . ?
N1 C3 1.391(5) . ?
N2 C4 1.373(5) . ?
N2 C5 1.386(5) . ?
N2 H2 0.80(3) . ?
N3 C5 1.362(5) . ?
N3 C6 1.408(4) . ?
N3 H3A 0.81(3) . ?
C9 C8 1.345(5) . ?
C9 C10 1.410(5) . ?
C9 H9 0.9300 . ?
C8 C7 1.409(5) . ?
C8 H8 0.9300 . ?
C7 C6 1.378(4) . ?
C7 H7 0.9300 . ?
C6 C15 1.438(5) . ?
C15 C14 1.417(5) . ?
C15 C10 1.419(5) . ?
C10 C11 1.405(5) . ?
C11 C12 1.361(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.392(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C3 C2 1.336(5) . ?
C3 H3 0.9300 . ?
C2 C1 1.515(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N4 C28 1.521(4) . ?
N4 C20 1.523(4) . ?
N4 C19 1.526(4) . ?
N4 C27 1.527(4) . ?
C19 C18 1.510(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C18 C17 1.632(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C17 C16 1.427(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C28 C29 1.505(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.517(4) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.502(5) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C20 C21 1.517(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.517(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.526(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C27 C26 1.520(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C26 C25 1.518(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C25 C24 1.510(5) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C4 S1 C2 89.2(2) . . ?
C4 N1 C3 108.5(4) . . ?
C4 N2 C5 124.3(4) . . ?
C4 N2 H2 118(3) . . ?
C5 N2 H2 117(3) . . ?
C5 N3 C6 124.2(3) . . ?
C5 N3 H3A 116(2) . . ?
C6 N3 H3A 118(2) . . ?
C8 C9 C10 121.4(4) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C8 C7 120.3(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C6 C7 C8 120.7(4) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C6 N3 120.6(4) . . ?
C7 C6 C15 119.9(4) . . ?
N3 C6 C15 119.5(3) . . ?
C14 C15 C10 118.7(4) . . ?
C14 C15 C6 123.4(4) . . ?
C10 C15 C6 117.9(3) . . ?
C11 C10 C9 122.7(4) . . ?
C11 C10 C15 117.6(4) . . ?
C9 C10 C15 119.7(4) . . ?
C12 C11 C10 123.0(4) . . ?
C12 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
C11 C12 C13 119.4(4) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 121.1(4) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
O1 C5 N3 125.4(4) . . ?
O1 C5 N2 121.3(4) . . ?
N3 C5 N2 113.2(4) . . ?
N1 C4 N2 121.0(4) . . ?
N1 C4 S1 115.6(3) . . ?
N2 C4 S1 123.4(3) . . ?
C2 C3 N1 117.9(4) . . ?
C2 C3 H3 121.1 . . ?
N1 C3 H3 121.1 . . ?
C3 C2 C1 129.1(5) . . ?
C3 C2 S1 108.8(4) . . ?
C1 C2 S1 122.1(4) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C28 N4 C20 112.0(2) . . ?
C28 N4 C19 111.4(2) . . ?
C20 N4 C19 105.9(2) . . ?
C28 N4 C27 105.3(2) . . ?
C20 N4 C27 111.5(2) . . ?
C19 N4 C27 110.9(2) . . ?
C18 C19 N4 117.0(3) . . ?
C18 C19 H19A 108.0 . . ?
N4 C19 H19A 108.0 . . ?
C18 C19 H19B 108.0 . . ?
N4 C19 H19B 108.0 . . ?
H19A C19 H19B 107.3 . . ?
C19 C18 C17 104.5(4) . . ?
C19 C18 H18A 110.8 . . ?
C17 C18 H18A 110.8 . . ?
C19 C18 H18B 110.8 . . ?
C17 C18 H18B 110.8 . . ?
H18A C18 H18B 108.9 . . ?
C16 C17 C18 115.1(7) . . ?
C16 C17 H17A 108.5 . . ?
C18 C17 H17A 108.5 . . ?
C16 C17 H17B 108.5 . . ?
C18 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C29 C28 N4 117.5(3) . . ?
C29 C28 H28A 107.9 . . ?
N4 C28 H28A 107.9 . . ?
C29 C28 H28B 107.9 . . ?
N4 C28 H28B 107.9 . . ?
H28A C28 H28B 107.2 . . ?
C28 C29 C30 109.8(3) . . ?
C28 C29 H29A 109.7 . . ?
C30 C29 H29A 109.7 . . ?
C28 C29 H29B 109.7 . . ?
C30 C29 H29B 109.7 . . ?
H29A C29 H29B 108.2 . . ?
C31 C30 C29 113.9(3) . . ?
C31 C30 H30A 108.8 . . ?
C29 C30 H30A 108.8 . . ?
C31 C30 H30B 108.8 . . ?
C29 C30 H30B 108.8 . . ?
H30A C30 H30B 107.7 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C21 C20 N4 117.7(3) . . ?
C21 C20 H20A 107.9 . . ?
N4 C20 H20A 107.9 . . ?
C21 C20 H20B 107.9 . . ?
N4 C20 H20B 107.9 . . ?
H20A C20 H20B 107.2 . . ?
C22 C21 C20 109.5(3) . . ?
C22 C21 H21A 109.8 . . ?
C20 C21 H21A 109.8 . . ?
C22 C21 H21B 109.8 . . ?
C20 C21 H21B 109.8 . . ?
H21A C21 H21B 108.2 . . ?
C21 C22 C23 113.2(3) . . ?
C21 C22 H22A 108.9 . . ?
C23 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
C23 C22 H22B 108.9 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C26 C27 N4 117.0(3) . . ?
C26 C27 H27A 108.0 . . ?
N4 C27 H27A 108.0 . . ?
C26 C27 H27B 108.0 . . ?
N4 C27 H27B 108.0 . . ?
H27A C27 H27B 107.3 . . ?
C25 C26 C27 108.8(3) . . ?
C25 C26 H26A 109.9 . . ?
C27 C26 H26A 109.9 . . ?
C25 C26 H26B 109.9 . . ?
C27 C26 H26B 109.9 . . ?
H26A C26 H26B 108.3 . . ?
C24 C25 C26 114.3(3) . . ?
C24 C25 H25A 108.7 . . ?
C26 C25 H25A 108.7 . . ?
C24 C25 H25B 108.7 . . ?
C26 C25 H25B 108.7 . . ?
H25A C25 H25B 107.6 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C10 C9 C8 C7 0.8(6) . . . . ?
C9 C8 C7 C6 0.1(6) . . . . ?
C8 C7 C6 N3 178.2(3) . . . . ?
C8 C7 C6 C15 -2.2(5) . . . . ?
C5 N3 C6 C7 -41.4(5) . . . . ?
C5 N3 C6 C15 139.0(3) . . . . ?
C7 C6 C15 C14 -177.5(3) . . . . ?
N3 C6 C15 C14 2.1(5) . . . . ?
C7 C6 C15 C10 3.2(5) . . . . ?
N3 C6 C15 C10 -177.1(3) . . . . ?
C8 C9 C10 C11 179.7(4) . . . . ?
C8 C9 C10 C15 0.3(6) . . . . ?
C14 C15 C10 C11 -1.0(5) . . . . ?
C6 C15 C10 C11 178.3(3) . . . . ?
C14 C15 C10 C9 178.4(3) . . . . ?
C6 C15 C10 C9 -2.3(5) . . . . ?
C9 C10 C11 C12 -178.7(4) . . . . ?
C15 C10 C11 C12 0.7(6) . . . . ?
C10 C11 C12 C13 -0.1(7) . . . . ?
C11 C12 C13 C14 -0.1(6) . . . . ?
C12 C13 C14 C15 -0.3(6) . . . . ?
C10 C15 C14 C13 0.9(5) . . . . ?
C6 C15 C14 C13 -178.4(3) . . . . ?
C6 N3 C5 O1 5.7(6) . . . . ?
C6 N3 C5 N2 -175.2(3) . . . . ?
C4 N2 C5 O1 -5.7(5) . . . . ?
C4 N2 C5 N3 175.2(3) . . . . ?
C3 N1 C4 N2 178.2(3) . . . . ?
C3 N1 C4 S1 -0.3(4) . . . . ?
C5 N2 C4 N1 -176.3(3) . . . . ?
C5 N2 C4 S1 2.1(5) . . . . ?
C2 S1 C4 N1 0.3(3) . . . . ?
C2 S1 C4 N2 -178.2(3) . . . . ?
C4 N1 C3 C2 0.2(5) . . . . ?
N1 C3 C2 C1 -177.8(4) . . . . ?
N1 C3 C2 S1 0.0(5) . . . . ?
C4 S1 C2 C3 -0.2(3) . . . . ?
C4 S1 C2 C1 177.9(4) . . . . ?
C28 N4 C19 C18 -60.6(4) . . . . ?
C20 N4 C19 C18 177.4(3) . . . . ?
C27 N4 C19 C18 56.3(4) . . . . ?
N4 C19 C18 C17 -178.5(4) . . . . ?
C19 C18 C17 C16 171.3(7) . . . . ?
C20 N4 C28 C29 60.7(4) . . . . ?
C19 N4 C28 C29 -57.6(4) . . . . ?
C27 N4 C28 C29 -177.9(3) . . . . ?
N4 C28 C29 C30 179.6(3) . . . . ?
C28 C29 C30 C31 179.8(3) . . . . ?
C28 N4 C20 C21 59.2(4) . . . . ?
C19 N4 C20 C21 -179.2(3) . . . . ?
C27 N4 C20 C21 -58.6(3) . . . . ?
N4 C20 C21 C22 175.8(3) . . . . ?
C20 C21 C22 C23 -173.3(3) . . . . ?
C28 N4 C27 C26 172.1(3) . . . . ?
C20 N4 C27 C26 -66.2(4) . . . . ?
C19 N4 C27 C26 51.5(4) . . . . ?
N4 C27 C26 C25 -178.7(3) . . . . ?
C27 C26 C25 C24 175.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_1d
_database_code_depnum_ccdc_archive 'CCDC 1453066'
_audit_update_record             
;
2016-02-12 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H51 Cl N4 O2 S'
_chemical_formula_weight         579.27

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'
Cl Cl 0.1484 0.1585 '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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4037(12)
_cell_length_b                   10.2399(15)
_cell_length_c                   19.874(3)
_cell_angle_alpha                97.051(7)
_cell_angle_beta                 95.211(7)
_cell_angle_gamma                94.056(7)
_cell_volume                     1684.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3094
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      19.28

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             628
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_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            11791
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.04
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5710
_reflns_number_gt                2871
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0101P)²+1.6000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5710
_refine_ls_number_parameters     373
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1024
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.262
_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
S1 S 0.65536(16) 0.42604(12) 0.05740(6) 0.0753(4) Uani 1 1 d . . .
O1 O 0.6426(4) 0.5812(3) 0.17909(15) 0.0800(10) Uani 1 1 d . . .
N1 N 0.6075(5) 0.1953(4) 0.09269(19) 0.0736(11) Uani 1 1 d . . .
N2 N 0.5905(5) 0.3618(4) 0.1822(2) 0.0665(11) Uani 1 1 d . . .
N3 N 0.5688(5) 0.5071(4) 0.2769(2) 0.0624(10) Uani 1 1 d . . .
C6 C 0.5589(5) 0.6290(4) 0.3177(2) 0.0573(11) Uani 1 1 d . . .
C7 C 0.5125(5) 0.7372(4) 0.2898(3) 0.0693(13) Uani 1 1 d . . .
H7 H 0.4908 0.7330 0.2429 0.083 Uiso 1 1 calc R . .
C8 C 0.4976(6) 0.8553(5) 0.3323(4) 0.0839(16) Uani 1 1 d . . .
H8 H 0.4683 0.9295 0.3131 0.101 Uiso 1 1 calc R . .
C9 C 0.5255(6) 0.8621(5) 0.4010(4) 0.0886(17) Uani 1 1 d . . .
H9 H 0.5110 0.9402 0.4282 0.106 Uiso 1 1 calc R . .
C10 C 0.5755(5) 0.7543(5) 0.4318(3) 0.0717(14) Uani 1 1 d . . .
C15 C 0.5956(5) 0.6345(4) 0.3897(2) 0.0580(11) Uani 1 1 d . . .
C14 C 0.6531(5) 0.5291(5) 0.4215(2) 0.0688(13) Uani 1 1 d . . .
H14 H 0.6675 0.4504 0.3949 0.083 Uiso 1 1 calc R . .
C13 C 0.6880(6) 0.5398(5) 0.4905(3) 0.0832(15) Uani 1 1 d . . .
H13 H 0.7277 0.4693 0.5102 0.100 Uiso 1 1 calc R . .
C12 C 0.6644(7) 0.6563(6) 0.5317(3) 0.0945(17) Uani 1 1 d . . .
H12 H 0.6866 0.6626 0.5788 0.113 Uiso 1 1 calc R . .
C11 C 0.6098(6) 0.7589(6) 0.5034(3) 0.0908(17) Uani 1 1 d . . .
H11 H 0.5939 0.8355 0.5315 0.109 Uiso 1 1 calc R . .
C5 C 0.6031(5) 0.4921(5) 0.2109(2) 0.0615(12) Uani 1 1 d . . .
C4 C 0.6153(5) 0.3197(4) 0.1156(2) 0.0615(12) Uani 1 1 d . . .
C3 C 0.6353(6) 0.1812(5) 0.0245(2) 0.0781(14) Uani 1 1 d . . .
H3 H 0.6349 0.0982 -0.0006 0.094 Uiso 1 1 calc R . .
C2 C 0.6626(6) 0.2910(5) -0.0036(2) 0.0703(13) Uani 1 1 d . . .
C1 C 0.6963(6) 0.3074(5) -0.0753(2) 0.0943(17) Uani 1 1 d . . .
H1A H 0.6893 0.2222 -0.1021 0.142 Uiso 1 1 calc R . .
H1B H 0.8020 0.3498 -0.0747 0.142 Uiso 1 1 calc R . .
H1C H 0.6190 0.3605 -0.0946 0.142 Uiso 1 1 calc R . .
N4 N 0.9654(4) 0.9787(4) 0.25535(17) 0.0649(10) Uani 1 1 d . . .
C20 C 1.0773(5) 1.0850(5) 0.2336(2) 0.0734(13) Uani 1 1 d . . .
H20A H 1.1525 1.1208 0.2725 0.088 Uiso 1 1 calc R . .
H20B H 1.1387 1.0439 0.1990 0.088 Uiso 1 1 calc R . .
C21 C 0.9988(6) 1.1983(5) 0.2060(3) 0.0903(16) Uani 1 1 d . . .
H21A H 0.9365 1.2412 0.2397 0.108 Uiso 1 1 calc R . .
H21B H 0.9269 1.1656 0.1655 0.108 Uiso 1 1 calc R . .
C22 C 1.1287(7) 1.2971(6) 0.1885(3) 0.1077(19) Uani 1 1 d . . .
H22A H 1.1938 1.3349 0.2301 0.129 Uiso 1 1 calc R . .
H22B H 1.1979 1.2507 0.1590 0.129 Uiso 1 1 calc R . .
C23 C 1.0628(8) 1.4051(6) 0.1544(3) 0.137(2) Uani 1 1 d . . .
H23A H 1.0054 1.3690 0.1114 0.205 Uiso 1 1 calc R . .
H23B H 1.1490 1.4667 0.1470 0.205 Uiso 1 1 calc R . .
H23C H 0.9913 1.4496 0.1827 0.205 Uiso 1 1 calc R . .
C27 C 0.8742(5) 1.0343(5) 0.3137(2) 0.0784(14) Uani 1 1 d . . .
H27A H 0.8036 1.0966 0.2970 0.094 Uiso 1 1 calc R . .
H27B H 0.8071 0.9624 0.3268 0.094 Uiso 1 1 calc R . .
C26 C 0.9747(7) 1.1025(6) 0.3768(3) 0.1072(19) Uani 1 1 d . . .
H26A H 1.0342 1.1813 0.3668 0.129 Uiso 1 1 calc R . .
H26B H 1.0499 1.0441 0.3941 0.129 Uiso 1 1 calc R . .
C25 C 0.8534(8) 1.1389(8) 0.4296(3) 0.159(3) Uani 1 1 d D . .
H25A H 0.7769 1.1937 0.4098 0.191 Uiso 1 1 calc R . .
H25B H 0.7943 1.0583 0.4376 0.191 Uiso 1 1 calc R . .
C24 C 0.9269(10) 1.2102(9) 0.4969(4) 0.211(4) Uani 1 1 d D . .
H24A H 1.0107 1.1614 0.5149 0.317 Uiso 1 1 calc RD . .
H24B H 0.8462 1.2181 0.5281 0.317 Uiso 1 1 calc R . .
H24C H 0.9707 1.2965 0.4908 0.317 Uiso 1 1 calc R . .
C19 C 1.0701(5) 0.8733(5) 0.2768(2) 0.0726(13) Uani 1 1 d . . .
H19A H 1.1503 0.9144 0.3128 0.087 Uiso 1 1 calc R . .
H19B H 1.1263 0.8412 0.2384 0.087 Uiso 1 1 calc R . .
C18 C 0.9854(6) 0.7550(5) 0.3019(3) 0.0823(15) Uani 1 1 d . . .
H18A H 0.9340 0.7841 0.3422 0.099 Uiso 1 1 calc R . .
H18B H 0.9031 0.7131 0.2670 0.099 Uiso 1 1 calc R . .
C17 C 1.1043(6) 0.6565(5) 0.3185(3) 0.0917(16) Uani 1 1 d . . .
H17A H 1.1878 0.6999 0.3525 0.110 Uiso 1 1 calc R . .
H17B H 1.1543 0.6273 0.2778 0.110 Uiso 1 1 calc R . .
C16 C 1.0277(7) 0.5373(5) 0.3451(3) 0.1121(19) Uani 1 1 d . . .
H16A H 0.9872 0.5645 0.3878 0.168 Uiso 1 1 calc R . .
H16B H 1.1063 0.4751 0.3515 0.168 Uiso 1 1 calc R . .
H16C H 0.9411 0.4966 0.3128 0.168 Uiso 1 1 calc R . .
C28 C 0.8392(5) 0.9217(5) 0.1974(2) 0.0713(13) Uani 1 1 d . . .
H28A H 0.7703 0.8548 0.2136 0.086 Uiso 1 1 calc R . .
H28B H 0.7733 0.9915 0.1862 0.086 Uiso 1 1 calc R . .
C29 C 0.9025(6) 0.8611(5) 0.1330(2) 0.0924(17) Uani 1 1 d . . .
H29A H 0.9808 0.9236 0.1188 0.111 Uiso 1 1 calc R . .
H29B H 0.9556 0.7830 0.1418 0.111 Uiso 1 1 calc R . .
C30 C 0.7683(6) 0.8240(5) 0.0767(2) 0.0971(17) Uani 1 1 d . . .
H30A H 0.6941 0.7578 0.0904 0.117 Uiso 1 1 calc R . .
H30B H 0.7106 0.9013 0.0708 0.117 Uiso 1 1 calc R . .
C31 C 0.8222(8) 0.7718(7) 0.0098(3) 0.148(3) Uani 1 1 d . . .
H31A H 0.8909 0.8385 -0.0057 0.222 Uiso 1 1 calc R . .
H31B H 0.7305 0.7478 -0.0230 0.222 Uiso 1 1 calc R . .
H31C H 0.8799 0.6954 0.0150 0.222 Uiso 1 1 calc R . .
Cl1 Cl 0.49359(15) 0.20581(10) 0.30341(6) 0.0710(4) Uani 1 1 d . . .
O2 O 0.4220(5) 0.0045(4) 0.1638(2) 0.1077(13) Uani 1 1 d D . .
H3A H 0.548(4) 0.436(4) 0.2948(19) 0.059(14) Uiso 1 1 d . . .
H2 H 0.566(4) 0.303(4) 0.2059(19) 0.051(13) Uiso 1 1 d . . .
H2P H 0.444(7) 0.051(5) 0.2068(14) 0.14(2) Uiso 1 1 d D . .
H2Q H 0.477(8) 0.059(6) 0.138(3) 0.19(4) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.722(4) . ?
S1 C2 1.732(4) . ?
O1 C5 1.216(5) . ?
N1 C4 1.294(5) . ?
N1 C3 1.388(5) . ?
N2 C5 1.378(5) . ?
N2 C4 1.380(5) . ?
N2 H2 0.84(4) . ?
N3 C5 1.361(5) . ?
N3 C6 1.415(5) . ?
N3 H3A 0.86(4) . ?
C6 C7 1.363(5) . ?
C6 C15 1.429(6) . ?
C7 C8 1.407(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.356(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.398(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.421(7) . ?
C10 C15 1.427(6) . ?
C15 C14 1.408(6) . ?
C14 C13 1.366(6) . ?
C14 H14 0.9300 . ?
C13 C12 1.398(6) . ?
C13 H13 0.9300 . ?
C12 C11 1.341(7) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C3 C2 1.331(6) . ?
C3 H3 0.9300 . ?
C2 C1 1.503(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N4 C20 1.516(5) . ?
N4 C19 1.517(5) . ?
N4 C28 1.522(5) . ?
N4 C27 1.523(5) . ?
C20 C21 1.511(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.528(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.480(7) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C27 C26 1.510(6) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C26 C25 1.559(7) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C25 C24 1.500(6) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C19 C18 1.521(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C18 C17 1.513(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C17 C16 1.514(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C28 C29 1.511(6) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.508(6) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.492(7) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
O2 H2P 0.922(17) . ?
O2 H2Q 0.924(17) . ?

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
C4 S1 C2 89.1(2) . . ?
C4 N1 C3 109.1(4) . . ?
C5 N2 C4 124.4(4) . . ?
C5 N2 H2 119(3) . . ?
C4 N2 H2 116(3) . . ?
C5 N3 C6 125.6(4) . . ?
C5 N3 H3A 117(3) . . ?
C6 N3 H3A 117(3) . . ?
C7 C6 N3 121.4(4) . . ?
C7 C6 C15 120.8(4) . . ?
N3 C6 C15 117.7(4) . . ?
C6 C7 C8 119.8(5) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 120.8(5) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 121.4(5) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C11 122.9(5) . . ?
C9 C10 C15 118.9(5) . . ?
C11 C10 C15 118.2(5) . . ?
C14 C15 C10 118.0(5) . . ?
C14 C15 C6 123.8(4) . . ?
C10 C15 C6 118.2(5) . . ?
C13 C14 C15 121.5(4) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C13 C12 120.3(5) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C11 C12 C13 120.0(5) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C11 C10 122.0(5) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
O1 C5 N3 125.5(4) . . ?
O1 C5 N2 121.8(4) . . ?
N3 C5 N2 112.7(4) . . ?
N1 C4 N2 121.2(4) . . ?
N1 C4 S1 115.5(3) . . ?
N2 C4 S1 123.3(4) . . ?
C2 C3 N1 117.4(4) . . ?
C2 C3 H3 121.3 . . ?
N1 C3 H3 121.3 . . ?
C3 C2 C1 129.6(4) . . ?
C3 C2 S1 108.9(4) . . ?
C1 C2 S1 121.5(4) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C20 N4 C19 106.3(3) . . ?
C20 N4 C28 111.2(3) . . ?
C19 N4 C28 111.0(3) . . ?
C20 N4 C27 111.2(3) . . ?
C19 N4 C27 111.0(3) . . ?
C28 N4 C27 106.2(3) . . ?
C21 C20 N4 116.2(4) . . ?
C21 C20 H20A 108.2 . . ?
N4 C20 H20A 108.2 . . ?
C21 C20 H20B 108.2 . . ?
N4 C20 H20B 108.2 . . ?
H20A C20 H20B 107.4 . . ?
C20 C21 C22 109.0(4) . . ?
C20 C21 H21A 109.9 . . ?
C22 C21 H21A 109.9 . . ?
C20 C21 H21B 109.9 . . ?
C22 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?
C23 C22 C21 113.0(5) . . ?
C23 C22 H22A 109.0 . . ?
C21 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
C21 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C26 C27 N4 116.3(4) . . ?
C26 C27 H27A 108.2 . . ?
N4 C27 H27A 108.2 . . ?
C26 C27 H27B 108.2 . . ?
N4 C27 H27B 108.2 . . ?
H27A C27 H27B 107.4 . . ?
C27 C26 C25 105.5(4) . . ?
C27 C26 H26A 110.6 . . ?
C25 C26 H26A 110.6 . . ?
C27 C26 H26B 110.6 . . ?
C25 C26 H26B 110.6 . . ?
H26A C26 H26B 108.8 . . ?
C24 C25 C26 115.1(6) . . ?
C24 C25 H25A 108.5 . . ?
C26 C25 H25A 108.5 . . ?
C24 C25 H25B 108.5 . . ?
C26 C25 H25B 108.5 . . ?
H25A C25 H25B 107.5 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N4 C19 C18 116.6(4) . . ?
N4 C19 H19A 108.1 . . ?
C18 C19 H19A 108.1 . . ?
N4 C19 H19B 108.1 . . ?
C18 C19 H19B 108.1 . . ?
H19A C19 H19B 107.3 . . ?
C17 C18 C19 110.2(4) . . ?
C17 C18 H18A 109.6 . . ?
C19 C18 H18A 109.6 . . ?
C17 C18 H18B 109.6 . . ?
C19 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
C18 C17 C16 112.8(4) . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C29 C28 N4 115.8(4) . . ?
C29 C28 H28A 108.3 . . ?
N4 C28 H28A 108.3 . . ?
C29 C28 H28B 108.3 . . ?
N4 C28 H28B 108.3 . . ?
H28A C28 H28B 107.4 . . ?
C30 C29 C28 110.9(4) . . ?
C30 C29 H29A 109.5 . . ?
C28 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 108.0 . . ?
C31 C30 C29 114.3(5) . . ?
C31 C30 H30A 108.7 . . ?
C29 C30 H30A 108.7 . . ?
C31 C30 H30B 108.7 . . ?
C29 C30 H30B 108.7 . . ?
H30A C30 H30B 107.6 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
H2P O2 H2Q 101(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
C5 N3 C6 C7 29.8(6) . . . . ?
C5 N3 C6 C15 -151.6(4) . . . . ?
N3 C6 C7 C8 177.4(4) . . . . ?
C15 C6 C7 C8 -1.2(6) . . . . ?
C6 C7 C8 C9 -1.4(7) . . . . ?
C7 C8 C9 C10 2.4(8) . . . . ?
C8 C9 C10 C11 178.3(5) . . . . ?
C8 C9 C10 C15 -0.7(7) . . . . ?
C9 C10 C15 C14 177.2(4) . . . . ?
C11 C10 C15 C14 -1.9(6) . . . . ?
C9 C10 C15 C6 -1.8(6) . . . . ?
C11 C10 C15 C6 179.1(4) . . . . ?
C7 C6 C15 C14 -176.2(4) . . . . ?
N3 C6 C15 C14 5.2(6) . . . . ?
C7 C6 C15 C10 2.8(6) . . . . ?
N3 C6 C15 C10 -175.8(4) . . . . ?
C10 C15 C14 C13 0.4(6) . . . . ?
C6 C15 C14 C13 179.3(4) . . . . ?
C15 C14 C13 C12 1.2(7) . . . . ?
C14 C13 C12 C11 -1.1(8) . . . . ?
C13 C12 C11 C10 -0.5(8) . . . . ?
C9 C10 C11 C12 -177.0(5) . . . . ?
C15 C10 C11 C12 2.0(7) . . . . ?
C6 N3 C5 O1 6.2(7) . . . . ?
C6 N3 C5 N2 -174.5(4) . . . . ?
C4 N2 C5 O1 -2.2(7) . . . . ?
C4 N2 C5 N3 178.5(4) . . . . ?
C3 N1 C4 N2 179.3(4) . . . . ?
C3 N1 C4 S1 0.2(5) . . . . ?
C5 N2 C4 N1 177.3(4) . . . . ?
C5 N2 C4 S1 -3.7(6) . . . . ?
C2 S1 C4 N1 -0.1(4) . . . . ?
C2 S1 C4 N2 -179.1(4) . . . . ?
C4 N1 C3 C2 -0.3(6) . . . . ?
N1 C3 C2 C1 179.9(5) . . . . ?
N1 C3 C2 S1 0.3(6) . . . . ?
C4 S1 C2 C3 -0.1(4) . . . . ?
C4 S1 C2 C1 -179.8(4) . . . . ?
C19 N4 C20 C21 176.6(4) . . . . ?
C28 N4 C20 C21 55.7(5) . . . . ?
C27 N4 C20 C21 -62.5(5) . . . . ?
N4 C20 C21 C22 178.5(4) . . . . ?
C20 C21 C22 C23 174.1(5) . . . . ?
C20 N4 C27 C26 -56.2(6) . . . . ?
C19 N4 C27 C26 61.9(5) . . . . ?
C28 N4 C27 C26 -177.3(4) . . . . ?
N4 C27 C26 C25 -175.6(5) . . . . ?
C27 C26 C25 C24 -179.3(7) . . . . ?
C20 N4 C19 C18 179.4(4) . . . . ?
C28 N4 C19 C18 -59.6(5) . . . . ?
C27 N4 C19 C18 58.3(5) . . . . ?
N4 C19 C18 C17 177.7(4) . . . . ?
C19 C18 C17 C16 178.9(4) . . . . ?
C20 N4 C28 C29 58.4(5) . . . . ?
C19 N4 C28 C29 -59.7(5) . . . . ?
C27 N4 C28 C29 179.6(4) . . . . ?
N4 C28 C29 C30 -172.8(4) . . . . ?
C28 C29 C30 C31 176.1(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.036


####################################################################### 
# 
# 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_1e
_database_code_depnum_ccdc_archive 'CCDC 1453067'
_audit_update_record             
;
2016-02-12 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H51 Cl N4 O2 S'
_chemical_formula_weight         579.27

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/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                   11.5868(16)
_cell_length_b                   15.626(2)
_cell_length_c                   19.065(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.020(9)
_cell_angle_gamma                90.00
_cell_volume                     3418.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2179
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      17.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1256
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_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            26384
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_sigmaI/netI    0.0979
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         25.25
_reflns_number_total             6171
_reflns_number_gt                2605
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0000P)²+3.3000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6171
_refine_ls_number_parameters     365
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.1919
_refine_ls_R_factor_gt           0.0902
_refine_ls_wR_factor_ref         0.2324
_refine_ls_wR_factor_gt          0.1919
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.143
_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
Cl1 Cl 0.84844(13) 1.00069(10) 0.18343(8) 0.1066(5) Uani 1 1 d . . .
S2 S 0.61991(16) 0.90626(11) 0.43046(9) 0.1206(7) Uani 1 1 d . . .
C6 C 0.4783(5) 0.9471(3) 0.1452(3) 0.0835(15) Uani 1 1 d . . .
C10 C 0.3869(6) 0.9183(3) 0.0239(4) 0.0904(16) Uani 1 1 d . . .
C15 C 0.4857(5) 0.9124(3) 0.0778(3) 0.0806(14) Uani 1 1 d . . .
C14 C 0.5858(5) 0.8717(3) 0.0601(3) 0.0926(16) Uani 1 1 d . . .
H14 H 0.6511 0.8663 0.0943 0.111 Uiso 1 1 calc R . .
C4 C 0.7191(6) 0.9374(3) 0.3763(3) 0.0985(17) Uani 1 1 d . . .
C7 C 0.3756(6) 0.9822(3) 0.1600(3) 0.0998(17) Uani 1 1 d . . .
H7 H 0.3708 1.0036 0.2050 0.120 Uiso 1 1 calc R . .
C3 C 0.8290(7) 0.9325(4) 0.4793(4) 0.122(2) Uani 1 1 d . . .
H3 H 0.8978 0.9382 0.5105 0.147 Uiso 1 1 calc R . .
C8 C 0.2765(6) 0.9860(4) 0.1067(5) 0.115(2) Uani 1 1 d . . .
H8 H 0.2068 1.0089 0.1172 0.138 Uiso 1 1 calc R . .
C9 C 0.2841(7) 0.9558(4) 0.0405(4) 0.113(2) Uani 1 1 d . . .
H9 H 0.2198 0.9601 0.0055 0.136 Uiso 1 1 calc R . .
C11 C 0.3948(7) 0.8850(4) -0.0439(4) 0.112(2) Uani 1 1 d . . .
H11 H 0.3312 0.8897 -0.0792 0.134 Uiso 1 1 calc R . .
C13 C 0.5891(6) 0.8400(4) -0.0060(4) 0.1108(19) Uani 1 1 d . . .
H13 H 0.6566 0.8135 -0.0164 0.133 Uiso 1 1 calc R . .
C2 C 0.7312(7) 0.9084(4) 0.5015(4) 0.120(2) Uani 1 1 d . . .
C12 C 0.4925(8) 0.8466(4) -0.0584(4) 0.121(2) Uani 1 1 d . . .
H12 H 0.4957 0.8244 -0.1034 0.145 Uiso 1 1 calc R . .
C1 C 0.7090(7) 0.8872(5) 0.5753(4) 0.158(3) Uani 1 1 d . . .
H1A H 0.7775 0.8997 0.6082 0.237 Uiso 1 1 calc R . .
H1B H 0.6904 0.8276 0.5781 0.237 Uiso 1 1 calc R . .
H1C H 0.6450 0.9209 0.5869 0.237 Uiso 1 1 calc R . .
N3 N 0.5795(4) 0.9476(3) 0.1963(3) 0.0956(13) Uani 1 1 d . . .
H3A H 0.6452 0.9558 0.1812 0.115 Uiso 1 1 calc R . .
N2 N 0.6918(4) 0.9491(3) 0.3043(3) 0.0989(14) Uani 1 1 d . . .
H2 H 0.7463 0.9653 0.2810 0.119 Uiso 1 1 calc R . .
N1 N 0.8254(5) 0.9491(3) 0.4074(3) 0.1087(15) Uani 1 1 d . . .
N4 N 0.1160(4) 0.7713(3) 0.2262(3) 0.0932(13) Uani 1 1 d . . .
C27 C 0.0210(5) 0.7181(4) 0.2522(3) 0.1089(19) Uani 1 1 d . . .
H27A H -0.0075 0.6773 0.2155 0.131 Uiso 1 1 calc R . .
H27B H 0.0556 0.6857 0.2932 0.131 Uiso 1 1 calc R . .
C25 C -0.1711(9) 0.6919(7) 0.2861(6) 0.222(5) Uani 1 1 d D . .
H25A H -0.2163 0.6745 0.2417 0.266 Uiso 1 1 calc R . .
H25B H -0.1286 0.6424 0.3068 0.266 Uiso 1 1 calc R . .
C24 C -0.2484(11) 0.7237(7) 0.3341(7) 0.271(6) Uani 1 1 d D . .
H24A H -0.2032 0.7513 0.3738 0.407 Uiso 1 1 calc R . .
H24B H -0.2909 0.6768 0.3506 0.407 Uiso 1 1 calc R . .
H24C H -0.3022 0.7640 0.3097 0.407 Uiso 1 1 calc R . .
C26 C -0.0808(6) 0.7667(5) 0.2720(4) 0.157(3) Uani 1 1 d . . .
H26A H -0.1141 0.8039 0.2337 0.189 Uiso 1 1 calc R . .
H26B H -0.0585 0.8007 0.3142 0.189 Uiso 1 1 calc R . .
C19 C 0.1639(5) 0.8380(4) 0.2804(4) 0.1080(19) Uani 1 1 d . . .
H19A H 0.2238 0.8704 0.2613 0.130 Uiso 1 1 calc R . .
H19B H 0.1016 0.8775 0.2868 0.130 Uiso 1 1 calc R . .
C17 C 0.2549(8) 0.8762(5) 0.4006(5) 0.161(3) Uani 1 1 d D . .
H17A H 0.1917 0.9170 0.3997 0.193 Uiso 1 1 calc R . .
H17B H 0.3188 0.9049 0.3824 0.193 Uiso 1 1 calc R . .
C18 C 0.2148(7) 0.8038(5) 0.3522(4) 0.142(3) Uani 1 1 d . . .
H18A H 0.1563 0.7708 0.3721 0.170 Uiso 1 1 calc R . .
H18B H 0.2799 0.7664 0.3473 0.170 Uiso 1 1 calc R . .
C16 C 0.2946(10) 0.8512(6) 0.4763(5) 0.220(5) Uani 1 1 d D . .
H16A H 0.2319 0.8233 0.4952 0.331 Uiso 1 1 calc R . .
H16B H 0.3175 0.9015 0.5037 0.331 Uiso 1 1 calc R . .
H16C H 0.3597 0.8129 0.4783 0.331 Uiso 1 1 calc R . .
C28 C 0.2106(5) 0.7085(3) 0.2116(3) 0.1092(19) Uani 1 1 d . . .
H28A H 0.2393 0.6788 0.2553 0.131 Uiso 1 1 calc R . .
H28B H 0.1761 0.6661 0.1779 0.131 Uiso 1 1 calc R . .
C29 C 0.3131(6) 0.7497(5) 0.1828(5) 0.162(3) Uani 1 1 d . . .
H29A H 0.3543 0.7864 0.2190 0.194 Uiso 1 1 calc R . .
H29B H 0.2839 0.7854 0.1426 0.194 Uiso 1 1 calc R . .
C31 C 0.4766(12) 0.6666(8) 0.2266(7) 0.308(8) Uani 1 1 d D . .
H31A H 0.4382 0.6277 0.2547 0.462 Uiso 1 1 calc R . .
H31B H 0.4898 0.7201 0.2512 0.462 Uiso 1 1 calc R . .
H31C H 0.5499 0.6427 0.2184 0.462 Uiso 1 1 calc R . .
C30 C 0.4032(9) 0.6809(7) 0.1585(7) 0.214(5) Uani 1 1 d D . .
H30A H 0.3642 0.6289 0.1404 0.256 Uiso 1 1 calc R . .
H30B H 0.4474 0.7043 0.1234 0.256 Uiso 1 1 calc R . .
C20 C 0.0682(5) 0.8205(4) 0.1598(4) 0.112(2) Uani 1 1 d . . .
H20A H 0.1312 0.8530 0.1441 0.134 Uiso 1 1 calc R . .
H20B H 0.0106 0.8611 0.1716 0.134 Uiso 1 1 calc R . .
C21 C 0.0125(8) 0.7647(6) 0.0986(5) 0.165(3) Uani 1 1 d . . .
H21A H -0.0662 0.7527 0.1077 0.198 Uiso 1 1 calc R . .
H21B H 0.0539 0.7105 0.1030 0.198 Uiso 1 1 calc R . .
C22 C 0.0021(17) 0.7912(9) 0.0168(9) 0.347(10) Uani 1 1 d D . .
H22A H 0.0770 0.7889 -0.0003 0.417 Uiso 1 1 calc R . .
H22B H -0.0531 0.7552 -0.0127 0.417 Uiso 1 1 calc R . .
C23 C -0.0401(10) 0.8787(10) 0.0192(7) 0.255(6) Uani 1 1 d D . .
H23A H -0.1111 0.8793 0.0398 0.382 Uiso 1 1 calc R . .
H23B H -0.0544 0.9015 -0.0279 0.382 Uiso 1 1 calc R . .
H23C H 0.0174 0.9131 0.0475 0.382 Uiso 1 1 calc R . .
O1 O 1.0059(5) 0.0264(3) 0.3357(4) 0.1404(17) Uani 1 1 d D . .
C5 C 0.5819(6) 0.9362(4) 0.2674(4) 0.0939(17) Uani 1 1 d . . .
O2 O 0.4981(4) 0.9166(3) 0.2962(2) 0.1193(14) Uani 1 1 d . . .
H1P H 0.954(9) 0.009(8) 0.366(5) 0.32(7) Uiso 1 1 d D . .
H2Q H 0.968(6) 0.015(5) 0.2902(19) 0.18(3) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 C4 1.719(6) . ?
S2 C2 1.735(7) . ?
C6 C7 1.374(7) . ?
C6 C15 1.407(7) . ?
C6 N3 1.417(6) . ?
C10 C9 1.402(8) . ?
C10 C11 1.407(8) . ?
C10 C15 1.431(7) . ?
C15 C14 1.405(7) . ?
C14 C13 1.360(7) . ?
C4 N1 1.303(7) . ?
C4 N2 1.377(7) . ?
C7 C8 1.424(8) . ?
C3 C2 1.319(8) . ?
C3 N1 1.388(8) . ?
C8 C9 1.363(9) . ?
C11 C12 1.344(9) . ?
C13 C12 1.397(9) . ?
C2 C1 1.503(9) . ?
N3 C5 1.364(7) . ?
N2 C5 1.381(7) . ?
N4 C27 1.517(6) . ?
N4 C20 1.518(7) . ?
N4 C19 1.518(7) . ?
N4 C28 1.525(6) . ?
C27 C26 1.494(8) . ?
C25 C24 1.455(7) . ?
C25 C26 1.617(10) . ?
C19 C18 1.510(8) . ?
C17 C18 1.492(9) . ?
C17 C16 1.503(9) . ?
C28 C29 1.520(8) . ?
C29 C30 1.611(10) . ?
C31 C30 1.465(7) . ?
C20 C21 1.527(9) . ?
C21 C22 1.601(16) . ?
C22 C23 1.454(8) . ?
C5 O2 1.219(6) . ?

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
C4 S2 C2 88.6(4) . . ?
C7 C6 C15 120.4(6) . . ?
C7 C6 N3 120.9(6) . . ?
C15 C6 N3 118.7(5) . . ?
C9 C10 C11 121.9(7) . . ?
C9 C10 C15 119.0(6) . . ?
C11 C10 C15 119.2(7) . . ?
C14 C15 C6 123.4(5) . . ?
C14 C15 C10 117.5(6) . . ?
C6 C15 C10 119.1(6) . . ?
C13 C14 C15 121.2(6) . . ?
N1 C4 N2 120.4(6) . . ?
N1 C4 S2 115.8(5) . . ?
N2 C4 S2 123.8(5) . . ?
C6 C7 C8 120.4(6) . . ?
C2 C3 N1 117.4(7) . . ?
C9 C8 C7 119.7(7) . . ?
C8 C9 C10 121.4(7) . . ?
C12 C11 C10 121.3(7) . . ?
C14 C13 C12 120.9(7) . . ?
C3 C2 C1 129.1(7) . . ?
C3 C2 S2 109.5(5) . . ?
C1 C2 S2 121.4(6) . . ?
C11 C12 C13 119.9(7) . . ?
C5 N3 C6 125.7(5) . . ?
C4 N2 C5 123.8(5) . . ?
C4 N1 C3 108.6(6) . . ?
C27 N4 C20 110.7(4) . . ?
C27 N4 C19 111.5(4) . . ?
C20 N4 C19 106.1(4) . . ?
C27 N4 C28 106.2(4) . . ?
C20 N4 C28 111.2(4) . . ?
C19 N4 C28 111.3(4) . . ?
C26 C27 N4 116.0(5) . . ?
C24 C25 C26 109.1(9) . . ?
C27 C26 C25 103.1(7) . . ?
C18 C19 N4 115.7(5) . . ?
C18 C17 C16 115.1(7) . . ?
C17 C18 C19 109.9(6) . . ?
C29 C28 N4 114.2(5) . . ?
C28 C29 C30 113.1(6) . . ?
C31 C30 C29 99.6(9) . . ?
N4 C20 C21 114.5(5) . . ?
C20 C21 C22 124.2(9) . . ?
C23 C22 C21 101.1(14) . . ?
O2 C5 N3 125.0(6) . . ?
O2 C5 N2 122.9(6) . . ?
N3 C5 N2 112.1(6) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.049



####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 1479504'
_audit_update_record             
;
2016-05-14 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N3 O S'
_chemical_formula_sum            'C15 H13 N3 O S'
_chemical_formula_weight         283.34

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   8.4428(8)
_cell_length_b                   22.3348(19)
_cell_length_c                   7.7119(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.990(6)
_cell_angle_gamma                90.00
_cell_volume                     1390.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1331
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      24.51

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592.0
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_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            7348
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.35
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2490
_reflns_number_gt                1604
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0000P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2490
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0725
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
S1 S 0.38290(9) 0.39308(3) 0.04275(10) 0.0630(2) Uani 1 1 d . . .
C15 C 0.4903(3) 0.65402(9) 0.4636(3) 0.0398(5) Uani 1 1 d . . .
C6 C 0.3294(3) 0.63042(9) 0.3743(3) 0.0397(6) Uani 1 1 d . . .
C9 C 0.3536(4) 0.73876(12) 0.5623(4) 0.0572(7) Uani 1 1 d . . .
C4 C 0.3750(3) 0.46133(9) 0.1442(3) 0.0442(6) Uani 1 1 d . . .
C7 C 0.1895(3) 0.66122(11) 0.3776(4) 0.0490(6) Uani 1 1 d . . .
C14 C 0.6393(3) 0.62589(11) 0.4614(4) 0.0479(6) Uani 1 1 d . . .
C10 C 0.5003(3) 0.70955(10) 0.5580(3) 0.0471(6) Uani 1 1 d . . .
C5 C 0.1929(3) 0.54552(10) 0.1795(3) 0.0465(6) Uani 1 1 d . . .
C2 C 0.6450(3) 0.44580(11) 0.2270(4) 0.0511(6) Uani 1 1 d . . .
C11 C 0.6590(4) 0.73352(13) 0.6465(4) 0.0616(8) Uani 1 1 d . . .
C3 C 0.5965(4) 0.39576(12) 0.1311(4) 0.0603(8) Uani 1 1 d . . .
C13 C 0.7896(3) 0.65126(13) 0.5474(4) 0.0631(8) Uani 1 1 d . . .
C1 C 0.8189(4) 0.46390(17) 0.3229(6) 0.0668(8) Uani 1 1 d . . .
C12 C 0.7987(4) 0.70526(14) 0.6410(4) 0.0699(9) Uani 1 1 d . . .
C8 C 0.2037(4) 0.71557(11) 0.4733(4) 0.0574(7) Uani 1 1 d . . .
N1 N 0.5173(2) 0.48340(8) 0.2367(3) 0.0452(5) Uani 1 1 d . . .
N3 N 0.3246(2) 0.57412(8) 0.2899(3) 0.0440(5) Uani 1 1 d . . .
N2 N 0.2233(3) 0.48883(9) 0.1223(3) 0.0509(6) Uani 1 1 d . . .
O1 O 0.05104(19) 0.56566(7) 0.1294(3) 0.0642(5) Uani 1 1 d . . .
H1A H 0.893(4) 0.4395(14) 0.285(5) 0.111(12) Uiso 1 1 d . . .
H1B H 0.838(4) 0.4644(13) 0.450(5) 0.101(13) Uiso 1 1 d . . .
H1C H 0.839(3) 0.5040(13) 0.294(4) 0.080(9) Uiso 1 1 d . . .
H3 H 0.658(3) 0.3682(11) 0.114(4) 0.065(8) Uiso 1 1 d . . .
H2 H 0.136(3) 0.4696(10) 0.050(4) 0.064(8) Uiso 1 1 d . . .
H3A H 0.420(3) 0.5531(10) 0.310(3) 0.062(8) Uiso 1 1 d . . .
H7 H 0.086(3) 0.6446(9) 0.312(3) 0.050(7) Uiso 1 1 d . . .
H8 H 0.105(3) 0.7345(10) 0.480(3) 0.067(8) Uiso 1 1 d . . .
H9 H 0.364(3) 0.7766(11) 0.628(4) 0.073(8) Uiso 1 1 d . . .
H11 H 0.662(3) 0.7698(11) 0.717(4) 0.072(8) Uiso 1 1 d . . .
H12 H 0.907(3) 0.7218(11) 0.703(4) 0.084(9) Uiso 1 1 d . . .
H13 H 0.883(3) 0.6304(11) 0.536(4) 0.071(8) Uiso 1 1 d . . .
H14 H 0.640(2) 0.5881(9) 0.404(3) 0.037(6) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.724(2) . ?
S1 C3 1.733(3) . ?
C15 C14 1.411(3) . ?
C15 C10 1.428(3) . ?
C15 C6 1.432(3) . ?
C6 C7 1.374(3) . ?
C6 N3 1.411(3) . ?
C9 C8 1.354(4) . ?
C9 C10 1.409(3) . ?
C4 N1 1.301(3) . ?
C4 N2 1.385(3) . ?
C7 C8 1.408(3) . ?
C14 C13 1.371(3) . ?
C10 C11 1.419(3) . ?
C5 O1 1.231(3) . ?
C5 N3 1.348(3) . ?
C5 N2 1.389(3) . ?
C2 C3 1.337(3) . ?
C2 N1 1.386(3) . ?
C2 C1 1.494(4) . ?
C11 C12 1.349(4) . ?
C13 C12 1.396(4) . ?

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
C4 S1 C3 87.99(13) . . ?
C14 C15 C10 118.2(2) . . ?
C14 C15 C6 123.7(2) . . ?
C10 C15 C6 118.1(2) . . ?
C7 C6 N3 123.1(2) . . ?
C7 C6 C15 120.5(2) . . ?
N3 C6 C15 116.41(19) . . ?
C8 C9 C10 120.6(2) . . ?
N1 C4 N2 124.8(2) . . ?
N1 C4 S1 115.57(17) . . ?
N2 C4 S1 119.59(17) . . ?
C6 C7 C8 120.0(2) . . ?
C13 C14 C15 120.9(2) . . ?
C9 C10 C11 121.8(2) . . ?
C9 C10 C15 119.5(2) . . ?
C11 C10 C15 118.7(2) . . ?
O1 C5 N3 124.9(2) . . ?
O1 C5 N2 119.1(2) . . ?
N3 C5 N2 116.0(2) . . ?
C3 C2 N1 114.8(2) . . ?
C3 C2 C1 126.7(3) . . ?
N1 C2 C1 118.5(2) . . ?
C12 C11 C10 121.3(3) . . ?
C2 C3 S1 111.2(2) . . ?
C14 C13 C12 120.7(3) . . ?
C11 C12 C13 120.2(3) . . ?
C9 C8 C7 121.3(3) . . ?
C4 N1 C2 110.43(19) . . ?
C5 N3 C6 128.4(2) . . ?
C4 N2 C5 128.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.036


