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

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

data_ardpm_psp_0m
_database_code_depnum_ccdc_archive 'CCDC 1557692'
_audit_update_record             
;
2017-06-21 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 Cl N4 O S'
_chemical_formula_weight         320.79

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   ' 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                   9.676(5)
_cell_length_b                   12.483(6)
_cell_length_c                   11.857(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.414(16)
_cell_angle_gamma                90.00
_cell_volume                     1416.7(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2067
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      21.10

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16684
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.92
_reflns_number_total             2740
_reflns_number_gt                1750
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0810P)²+0.0308P] 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         2740
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1393
_refine_ls_wR_factor_gt          0.1182
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_restrained_S_all      0.970
_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 0.59677(10) 0.61305(6) 0.15370(7) 0.0689(3) Uani 1 1 d . . .
S1 S 0.82963(8) 0.47179(6) 0.07644(6) 0.0499(3) Uani 1 1 d . . .
O1 O 1.0591(2) 0.28594(16) 0.18569(15) 0.0541(6) Uani 1 1 d . . .
N1 N 0.4519(3) 0.4392(2) 0.1680(2) 0.0559(7) Uani 1 1 d . . .
N4 N 1.0602(2) 0.23203(18) -0.00118(17) 0.0430(6) Uani 1 1 d . . .
N3 N 0.9946(2) 0.26354(18) -0.10706(17) 0.0429(6) Uani 1 1 d . . .
H1 H 1.0072 0.2354 -0.1710 0.051 Uiso 1 1 calc R . .
N2 N 0.6540(3) 0.30660(19) 0.0985(2) 0.0531(6) Uani 1 1 d . . .
C4 C 0.4320(3) 0.3335(3) 0.1572(3) 0.0619(9) Uani 1 1 d . . .
H6 H 0.3490 0.3035 0.1730 0.074 Uiso 1 1 calc R . .
C1 C 0.5703(3) 0.4755(2) 0.1425(2) 0.0461(7) Uani 1 1 d . . .
C2 C 0.6742(3) 0.4115(2) 0.1065(2) 0.0421(7) Uani 1 1 d . . .
C6 C 0.9159(3) 0.3668(2) 0.0200(2) 0.0412(7) Uani 1 1 d . . .
C5 C 1.0131(3) 0.2960(2) 0.0819(2) 0.0417(7) Uani 1 1 d . . .
C9 C 1.1432(3) 0.1380(2) 0.0104(2) 0.0398(6) Uani 1 1 d . . .
C10 C 1.2348(3) 0.1176(2) -0.0657(2) 0.0491(7) Uani 1 1 d . . .
H7 H 1.2456 0.1668 -0.1227 0.059 Uiso 1 1 calc R . .
C11 C 1.3107(4) 0.0231(3) -0.0566(3) 0.0617(9) Uani 1 1 d . . .
H8 H 1.3725 0.0087 -0.1078 0.074 Uiso 1 1 calc R . .
C12 C 1.2953(4) -0.0493(3) 0.0278(3) 0.0676(10) Uani 1 1 d . . .
H9 H 1.3467 -0.1125 0.0338 0.081 Uiso 1 1 calc R . .
C13 C 1.2038(4) -0.0282(2) 0.1032(3) 0.0596(9) Uani 1 1 d . . .
H10 H 1.1934 -0.0779 0.1598 0.072 Uiso 1 1 calc R . .
C14 C 1.1271(3) 0.0654(2) 0.0965(2) 0.0513(8) Uani 1 1 d . . .
H11 H 1.0660 0.0796 0.1484 0.062 Uiso 1 1 calc R . .
C7 C 0.9083(3) 0.3447(2) -0.0946(2) 0.0404(6) Uani 1 1 d . . .
C8 C 0.8272(3) 0.3976(3) -0.1964(2) 0.0567(8) Uani 1 1 d . . .
H3 H 0.8636 0.4683 -0.2049 0.085 Uiso 1 1 calc R . .
H4 H 0.7307 0.4024 -0.1865 0.085 Uiso 1 1 calc R . .
H2 H 0.8353 0.3562 -0.2634 0.085 Uiso 1 1 calc R . .
C3 C 0.5318(3) 0.2696(3) 0.1234(3) 0.0595(8) Uani 1 1 d . . .
H5 H 0.5146 0.1964 0.1171 0.071 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
Cl1 C1 1.738(3) . ?
S1 C6 1.739(3) . ?
S1 C2 1.764(3) . ?
O1 C5 1.252(3) . ?
N1 C1 1.308(4) . ?
N1 C4 1.337(4) . ?
N4 N3 1.379(3) . ?
N4 C5 1.396(3) . ?
N4 C9 1.418(3) . ?
N3 C7 1.335(3) . ?
N3 H1 0.8600 . ?
N2 C2 1.325(3) . ?
N2 C3 1.342(4) . ?
C4 C3 1.358(4) . ?
C4 H6 0.9300 . ?
C1 C2 1.399(4) . ?
C6 C7 1.378(4) . ?
C6 C5 1.415(4) . ?
C9 C10 1.378(4) . ?
C9 C14 1.391(4) . ?
C10 C11 1.385(4) . ?
C10 H7 0.9300 . ?
C11 C12 1.372(5) . ?
C11 H8 0.9300 . ?
C12 C13 1.372(5) . ?
C12 H9 0.9300 . ?
C13 C14 1.381(4) . ?
C13 H10 0.9300 . ?
C14 H11 0.9300 . ?
C7 C8 1.494(4) . ?
C8 H3 0.9600 . ?
C8 H4 0.9600 . ?
C8 H2 0.9600 . ?
C3 H5 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
C6 S1 C2 103.18(13) . . ?
C1 N1 C4 116.0(3) . . ?
N3 N4 C5 109.0(2) . . ?
N3 N4 C9 120.2(2) . . ?
C5 N4 C9 130.1(2) . . ?
C7 N3 N4 109.2(2) . . ?
C7 N3 H1 125.4 . . ?
N4 N3 H1 125.4 . . ?
C2 N2 C3 116.7(3) . . ?
N1 C4 C3 120.7(3) . . ?
N1 C4 H6 119.7 . . ?
C3 C4 H6 119.7 . . ?
N1 C1 C2 124.5(3) . . ?
N1 C1 Cl1 116.7(2) . . ?
C2 C1 Cl1 118.9(2) . . ?
N2 C2 C1 118.8(3) . . ?
N2 C2 S1 121.9(2) . . ?
C1 C2 S1 119.3(2) . . ?
C7 C6 C5 108.8(2) . . ?
C7 C6 S1 124.8(2) . . ?
C5 C6 S1 126.2(2) . . ?
O1 C5 N4 122.0(2) . . ?
O1 C5 C6 133.4(2) . . ?
N4 C5 C6 104.6(2) . . ?
C10 C9 C14 120.8(3) . . ?
C10 C9 N4 119.9(2) . . ?
C14 C9 N4 119.2(3) . . ?
C9 C10 C11 119.4(3) . . ?
C9 C10 H7 120.3 . . ?
C11 C10 H7 120.3 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H8 119.8 . . ?
C10 C11 H8 119.8 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H9 120.1 . . ?
C11 C12 H9 120.1 . . ?
C12 C13 C14 121.2(3) . . ?
C12 C13 H10 119.4 . . ?
C14 C13 H10 119.4 . . ?
C13 C14 C9 118.4(3) . . ?
C13 C14 H11 120.8 . . ?
C9 C14 H11 120.8 . . ?
N3 C7 C6 108.5(2) . . ?
N3 C7 C8 120.6(2) . . ?
C6 C7 C8 130.9(3) . . ?
C7 C8 H3 109.5 . . ?
C7 C8 H4 109.5 . . ?
H3 C8 H4 109.5 . . ?
C7 C8 H2 109.5 . . ?
H3 C8 H2 109.5 . . ?
H4 C8 H2 109.5 . . ?
N2 C3 C4 123.3(3) . . ?
N2 C3 H5 118.3 . . ?
C4 C3 H5 118.3 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.92
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.097
####################################################################### 
# 
# 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_ard_pm_3cl_0m
_database_code_depnum_ccdc_archive 'CCDC 1557690'
_audit_update_record             
;
2017-06-21 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 Cl N2 O S'
_chemical_formula_weight         316.79

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   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
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                   42.263(6)
_cell_length_b                   5.9743(8)
_cell_length_c                   11.7282(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.856(5)
_cell_angle_gamma                90.00
_cell_volume                     2959.7(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3295
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      21.24

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    0.398
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16616
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         0.96
_diffrn_reflns_theta_max         25.91
_reflns_number_total             2843
_reflns_number_gt                1972
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0852P)²+1.2247P] 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         2843
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1479
_refine_ls_wR_factor_gt          0.1303
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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 0.03835(2) 0.43758(18) 0.14920(9) 0.0985(4) Uani 1 1 d . . .
S1 S 0.114744(17) -0.26632(12) 0.05076(5) 0.0609(3) Uani 1 1 d . . .
O1 O 0.16751(4) 0.1289(3) 0.05181(13) 0.0638(5) Uani 1 1 d . . .
N1 N 0.16909(5) 0.1027(4) 0.24954(15) 0.0505(5) Uani 1 1 d . . .
N2 N 0.15456(5) -0.0334(4) 0.32757(16) 0.0522(5) Uani 1 1 d . . .
H8 H 0.1578 -0.0289 0.4003 0.063 Uiso 1 1 calc R . .
C1 C 0.03133(8) 0.1806(8) -0.0403(3) 0.0988(12) Uani 1 1 d . . .
H1 H 0.0143 0.2717 -0.0613 0.119 Uiso 1 1 calc R . .
C2 C 0.04877(7) 0.2209(6) 0.0592(3) 0.0727(8) Uani 1 1 d . . .
C3 C 0.07431(6) 0.0898(5) 0.0896(2) 0.0606(7) Uani 1 1 d . . .
H4 H 0.0860 0.1194 0.1564 0.073 Uiso 1 1 calc R . .
C4 C 0.08249(6) -0.0856(5) 0.0207(2) 0.0592(7) Uani 1 1 d . . .
C7 C 0.13568(6) -0.1288(4) 0.15830(19) 0.0471(6) Uani 1 1 d . . .
C8 C 0.15806(6) 0.0425(4) 0.14095(19) 0.0486(6) Uani 1 1 d . . .
C11 C 0.18965(5) 0.2768(4) 0.2848(2) 0.0487(6) Uani 1 1 d . . .
C12 C 0.20393(7) 0.2741(5) 0.3918(2) 0.0644(8) Uani 1 1 d . . .
H9 H 0.2002 0.1568 0.4418 0.077 Uiso 1 1 calc R . .
C13 C 0.22376(7) 0.4471(6) 0.4239(3) 0.0795(9) Uani 1 1 d . . .
H10 H 0.2334 0.4459 0.4962 0.095 Uiso 1 1 calc R . .
C14 C 0.22951(7) 0.6205(6) 0.3519(3) 0.0762(9) Uani 1 1 d . . .
H11 H 0.2431 0.7358 0.3746 0.091 Uiso 1 1 calc R . .
C5 C 0.06476(8) -0.1293(7) -0.0786(3) 0.0833(10) Uani 1 1 d . . .
H3 H 0.0700 -0.2489 -0.1251 0.100 Uiso 1 1 calc R . .
C6 C 0.03958(9) 0.0052(8) -0.1071(3) 0.1055(13) Uani 1 1 d . . .
H2 H 0.0278 -0.0239 -0.1738 0.127 Uiso 1 1 calc R . .
C16 C 0.19502(6) 0.4509(5) 0.2114(2) 0.0580(7) Uani 1 1 d . . .
H13 H 0.1852 0.4532 0.1392 0.070 Uiso 1 1 calc R . .
C15 C 0.21506(7) 0.6229(5) 0.2457(3) 0.0713(8) Uani 1 1 d . . .
H12 H 0.2187 0.7410 0.1962 0.086 Uiso 1 1 calc R . .
C9 C 0.13493(6) -0.1711(4) 0.2732(2) 0.0489(6) Uani 1 1 d . . .
C10 C 0.11700(8) -0.3417(5) 0.3351(2) 0.0710(8) Uani 1 1 d . . .
H6 H 0.1259 -0.4867 0.3219 0.106 Uiso 1 1 calc R . .
H5 H 0.0953 -0.3400 0.3084 0.106 Uiso 1 1 calc R . .
H7 H 0.1181 -0.3093 0.4153 0.106 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
Cl1 C2 1.736(4) . ?
S1 C7 1.725(2) . ?
S1 C4 1.766(3) . ?
O1 C8 1.243(3) . ?
N1 N2 1.383(3) . ?
N1 C8 1.389(3) . ?
N1 C11 1.409(3) . ?
N2 C9 1.318(3) . ?
N2 H8 0.8600 . ?
C1 C6 1.361(6) . ?
C1 C2 1.382(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(4) . ?
C3 C4 1.374(4) . ?
C3 H4 0.9300 . ?
C4 C5 1.389(4) . ?
C7 C9 1.373(3) . ?
C7 C8 1.413(4) . ?
C11 C16 1.373(4) . ?
C11 C12 1.375(3) . ?
C12 C13 1.375(4) . ?
C12 H9 0.9300 . ?
C13 C14 1.363(4) . ?
C13 H10 0.9300 . ?
C14 C15 1.369(4) . ?
C14 H11 0.9300 . ?
C5 C6 1.366(5) . ?
C5 H3 0.9300 . ?
C6 H2 0.9300 . ?
C16 C15 1.383(4) . ?
C16 H13 0.9300 . ?
C15 H12 0.9300 . ?
C9 C10 1.475(4) . ?
C10 H6 0.9600 . ?
C10 H5 0.9600 . ?
C10 H7 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
C7 S1 C4 103.24(12) . . ?
N2 N1 C8 108.15(19) . . ?
N2 N1 C11 121.53(18) . . ?
C8 N1 C11 130.2(2) . . ?
C9 N2 N1 109.45(18) . . ?
C9 N2 H8 125.3 . . ?
N1 N2 H8 125.3 . . ?
C6 C1 C2 118.8(3) . . ?
C6 C1 H1 120.6 . . ?
C2 C1 H1 120.6 . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 Cl1 118.8(2) . . ?
C1 C2 Cl1 120.3(3) . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H4 120.2 . . ?
C4 C3 H4 120.2 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 S1 123.82(19) . . ?
C5 C4 S1 116.4(2) . . ?
C9 C7 C8 108.2(2) . . ?
C9 C7 S1 127.0(2) . . ?
C8 C7 S1 124.72(18) . . ?
O1 C8 N1 123.8(2) . . ?
O1 C8 C7 131.0(2) . . ?
N1 C8 C7 105.2(2) . . ?
C16 C11 C12 120.3(2) . . ?
C16 C11 N1 119.2(2) . . ?
C12 C11 N1 120.5(2) . . ?
C11 C12 C13 119.1(3) . . ?
C11 C12 H9 120.5 . . ?
C13 C12 H9 120.5 . . ?
C14 C13 C12 121.4(3) . . ?
C14 C13 H10 119.3 . . ?
C12 C13 H10 119.3 . . ?
C13 C14 C15 119.2(3) . . ?
C13 C14 H11 120.4 . . ?
C15 C14 H11 120.4 . . ?
C6 C5 C4 119.3(3) . . ?
C6 C5 H3 120.3 . . ?
C4 C5 H3 120.3 . . ?
C1 C6 C5 121.6(3) . . ?
C1 C6 H2 119.2 . . ?
C5 C6 H2 119.2 . . ?
C11 C16 C15 119.5(3) . . ?
C11 C16 H13 120.2 . . ?
C15 C16 H13 120.2 . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H12 119.7 . . ?
C16 C15 H12 119.7 . . ?
N2 C9 C7 109.0(2) . . ?
N2 C9 C10 121.2(2) . . ?
C7 C9 C10 129.7(2) . . ?
C9 C10 H6 109.5 . . ?
C9 C10 H5 109.5 . . ?
H6 C10 H5 109.5 . . ?
C9 C10 H7 109.5 . . ?
H6 C10 H7 109.5 . . ?
H5 C10 H7 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.91
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.045
