# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1858431'
_audit_update_record             
;
2018-07-26 deposited with the CCDC.
2018-10-19 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Hamada_BT4_24_07_11
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H11 N5 O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         369.40

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.43370(10)
_cell_length_b                   11.1793(3)
_cell_length_c                   12.2318(3)
_cell_angle_alpha                93.9110(10)
_cell_angle_beta                 94.6660(10)
_cell_angle_gamma                94.2320(10)
_cell_volume                     872.02(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9007
_cell_measurement_theta_min      3.6357
_cell_measurement_theta_max      66.1336
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380

_exptl_absorpt_coefficient_mu    1.822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.95

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            14792
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_theta_min         3.64
_diffrn_reflns_theta_max         66.44
_diffrn_reflns_theta_full        66.44
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14

_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.
;

_reflns_number_total             3014
_reflns_number_gt                2793
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1125
_refine_ls_goodness_of_fit_ref   1.684
_refine_ls_restrained_S_all      1.684
_refine_ls_number_reflns         3014
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0509P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2011.2.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.19450(5) 0.42184(3) -0.06969(3) 0.05443(17) Uani d . 1 . .
C C7 0.4116(2) 0.33738(11) -0.05424(11) 0.0438(3) Uani d . 1 . .
C C8 0.59892(19) 0.18084(11) 0.03618(10) 0.0423(3) Uani d . 1 . .
C C10 0.46137(19) 0.09273(11) 0.19867(10) 0.0431(3) Uani d . 1 . .
C C11 0.3098(2) 0.17495(12) 0.19631(10) 0.0445(3) Uani d . 1 . .
C C12 0.2866(2) 0.25599(12) 0.11137(11) 0.0456(3) Uani d . 1 . .
C C9 0.60358(19) 0.09713(11) 0.11764(10) 0.0436(3) Uani d . 1 . .
C C20 0.1717(2) 0.18886(12) 0.28100(12) 0.0488(3) Uani d . 1 . .
C C19 0.7555(2) 0.01115(12) 0.10792(10) 0.0462(3) Uani d . 1 . .
C C13 0.4713(2) 0.00248(11) 0.28165(10) 0.0455(3) Uani d . 1 . .
C C6 0.4873(2) 0.43069(12) -0.20118(11) 0.0490(3) Uani d . 1 . .
C C5 0.6015(3) 0.46647(13) -0.28743(13) 0.0579(4) Uani d . 1 . .
H H5 0.7285 0.4352 -0.2993 0.069 Uiso calc R 1 . .
C C18 0.2925(2) -0.06776(12) 0.30139(12) 0.0532(3) Uani d . 1 . .
H H18 0.1648 -0.0569 0.2634 0.064 Uiso calc R 1 . .
C C1 0.2976(2) 0.47824(12) -0.18382(12) 0.0518(3) Uani d . 1 . .
C C3 0.3317(3) 0.59646(15) -0.33607(14) 0.0670(4) Uani d . 1 . .
H H3 0.2809 0.6521 -0.3826 0.08 Uiso calc R 1 . .
C C14 0.6605(2) -0.01387(14) 0.34048(11) 0.0554(4) Uani d . 1 . .
H H14 0.781 0.033 0.3285 0.066 Uiso calc R 1 . .
C C2 0.2190(3) 0.56331(15) -0.25183(14) 0.0649(4) Uani d . 1 . .
H H2 0.0935 0.5962 -0.2398 0.078 Uiso calc R 1 . .
C C4 0.5217(3) 0.54875(14) -0.35416(13) 0.0625(4) Uani d . 1 . .
H H4 0.5951 0.5731 -0.4123 0.075 Uiso calc R 1 . .
C C16 0.4935(3) -0.16939(16) 0.43456(14) 0.0729(5) Uani d . 1 . .
H H16 0.5011 -0.2275 0.4853 0.087 Uiso calc R 1 . .
C C17 0.3042(3) -0.15373(14) 0.37741(14) 0.0667(4) Uani d . 1 . .
H H17 0.1847 -0.201 0.3901 0.08 Uiso calc R 1 . .
C C15 0.6695(3) -0.09979(16) 0.41682(13) 0.0674(4) Uani d . 1 . .
H H15 0.796 -0.1101 0.4562 0.081 Uiso calc R 1 . .
O O1 0.14494(17) 0.32314(10) 0.10379(9) 0.0602(3) Uani d . 1 . .
N N2 0.43788(16) 0.25856(9) 0.03183(9) 0.0430(3) Uani d . 1 . .
N N1 0.54706(19) 0.35016(11) -0.12603(10) 0.0510(3) Uani d . 1 . .
N N3 0.73808(18) 0.18499(11) -0.03662(10) 0.0535(3) Uani d . 1 . .
H H3A 0.73 0.2353 -0.0867 0.064 Uiso calc R 1 . .
H H3B 0.8372 0.1374 -0.0342 0.064 Uiso calc R 1 . .
N N4 0.8784(2) -0.05554(12) 0.09285(10) 0.0579(3) Uani d . 1 . .
N N5 0.0639(2) 0.20485(12) 0.34958(11) 0.0637(4) Uani d . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 . 1.7307(14) ?
S1 C7 . 1.7478(13) ?
C7 N1 . 1.2938(18) ?
C7 N2 . 1.4257(17) ?
C8 N3 . 1.3137(17) ?
C8 N2 . 1.4006(16) ?
C8 C9 . 1.4128(18) ?
C10 C11 . 1.3883(18) ?
C10 C9 . 1.4034(19) ?
C10 C13 . 1.4801(18) ?
C11 C20 . 1.4266(19) ?
C11 C12 . 1.4303(18) ?
C12 O1 . 1.2245(16) ?
C12 N2 . 1.4314(17) ?
C9 C19 . 1.4263(18) ?
C20 N5 . 1.1445(18) ?
C19 N4 . 1.1435(18) ?
C13 C18 . 1.392(2) ?
C13 C14 . 1.393(2) ?
C6 N1 . 1.3819(17) ?
C6 C1 . 1.393(2) ?
C6 C5 . 1.397(2) ?
C5 C4 . 1.371(2) ?
C18 C17 . 1.384(2) ?
C1 C2 . 1.401(2) ?
C3 C2 . 1.363(2) ?
C3 C4 . 1.397(2) ?
C14 C15 . 1.385(2) ?
C16 C15 . 1.367(3) ?
C16 C17 . 1.383(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 S1 C7 . . 88.12(6) ?
N1 C7 N2 . . 121.87(11) ?
N1 C7 S1 . . 115.97(10) ?
N2 C7 S1 . . 122.16(9) ?
N3 C8 N2 . . 119.71(12) ?
N3 C8 C9 . . 121.60(11) ?
N2 C8 C9 . . 118.66(11) ?
C11 C10 C9 . . 117.20(12) ?
C11 C10 C13 . . 121.74(12) ?
C9 C10 C13 . . 121.04(11) ?
C10 C11 C20 . . 122.57(12) ?
C10 C11 C12 . . 122.55(12) ?
C20 C11 C12 . . 114.83(11) ?
O1 C12 N2 . . 118.71(12) ?
O1 C12 C11 . . 123.36(12) ?
N2 C12 C11 . . 117.93(11) ?
C10 C9 C8 . . 123.06(11) ?
C10 C9 C19 . . 121.60(12) ?
C8 C9 C19 . . 115.22(11) ?
N5 C20 C11 . . 177.20(15) ?
N4 C19 C9 . . 175.25(14) ?
C18 C13 C14 . . 119.12(12) ?
C18 C13 C10 . . 120.53(12) ?
C14 C13 C10 . . 120.36(12) ?
N1 C6 C1 . . 114.04(12) ?
N1 C6 C5 . . 125.52(13) ?
C1 C6 C5 . . 120.43(12) ?
C4 C5 C6 . . 118.36(14) ?
C17 C18 C13 . . 120.11(14) ?
C6 C1 C2 . . 120.62(13) ?
C6 C1 S1 . . 110.62(10) ?
C2 C1 S1 . . 128.72(12) ?
C2 C3 C4 . . 121.49(14) ?
C15 C14 C13 . . 120.09(14) ?
C3 C2 C1 . . 118.15(15) ?
C5 C4 C3 . . 120.94(14) ?
C15 C16 C17 . . 120.29(14) ?
C16 C17 C18 . . 120.04(15) ?
C16 C15 C14 . . 120.33(15) ?
C8 N2 C7 . . 121.76(11) ?
C8 N2 C12 . . 120.32(11) ?
C7 N2 C12 . . 117.83(10) ?
C7 N1 C6 . . 111.24(11) ?

####################################################################### 
# 
# 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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1858432'
_audit_update_record             
;
2018-07-26 deposited with the CCDC.
2018-10-19 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Hamada_BTg_11_07_11
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 N6 O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         456.52

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3107(2)
_cell_length_b                   10.8553(2)
_cell_length_c                   12.3036(3)
_cell_angle_alpha                71.3360(10)
_cell_angle_beta                 71.5960(10)
_cell_angle_gamma                84.7560(10)
_cell_volume                     1117.81(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476

_exptl_absorpt_coefficient_mu    1.572
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   
;
;
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_T_max  0.91

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            13761
_diffrn_reflns_av_R_equivalents  0.1224
_diffrn_reflns_av_sigmaI/netI    0.0696
_diffrn_reflns_theta_min         3.98
_diffrn_reflns_theta_max         66.61
_diffrn_reflns_theta_full        66.61
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_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.
;

_reflns_number_total             3833
_reflns_number_gt                3579
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0725
_refine_ls_wR_factor_gt          0.2130
_refine_ls_wR_factor_ref         0.2166
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_number_reflns         3833
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1277P)²+0.4975P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.032
_refine_diff_density_min         -0.434
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0026(12)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 1.15440(9) -0.00710(7) 0.11558(6) 0.0611(3) Uani d . 1 . .
C C8 0.9345(3) 0.3251(2) -0.0107(2) 0.0428(5) Uani d . 1 . .
C C10 0.7437(3) 0.3651(2) 0.1653(2) 0.0448(6) Uani d . 1 . .
C C12 0.8943(3) 0.1659(3) 0.1915(2) 0.0504(6) Uani d . 1 . .
C C9 0.8241(3) 0.4034(2) 0.0427(2) 0.0420(5) Uani d . 1 . .
C C11 0.7771(3) 0.2471(3) 0.2372(2) 0.0493(6) Uani d . 1 . .
C C13 0.8011(3) 0.5300(2) -0.0327(2) 0.0435(5) Uani d . 1 . .
C C7 1.0922(3) 0.1287(2) 0.0198(2) 0.0461(6) Uani d . 1 . .
C C6 1.2784(3) 0.0659(3) -0.1147(3) 0.0531(6) Uani d . 1 . .
C C15 0.6238(3) 0.4493(3) 0.2147(2) 0.0461(6) Uani d . 1 . .
C C16 0.4984(3) 0.4787(3) 0.1740(2) 0.0524(6) Uani d . 1 . .
H H16 0.4893 0.4441 0.1165 0.063 Uiso calc R 1 . .
C C20 0.6344(3) 0.5026(3) 0.3017(2) 0.0530(6) Uani d . 1 . .
H H20 0.7168 0.4834 0.3315 0.064 Uiso calc R 1 . .
C C1 1.2895(3) -0.0290(3) -0.0095(3) 0.0562(7) Uani d . 1 . .
C C18 0.3979(3) 0.6142(3) 0.3030(2) 0.0546(7) Uani d . 1 . .
C C19 0.5231(3) 0.5833(3) 0.3431(2) 0.0572(7) Uani d . 1 . .
H H19 0.5325 0.6184 0.4004 0.069 Uiso calc R 1 . .
C C17 0.3870(3) 0.5586(3) 0.2175(3) 0.0568(7) Uani d . 1 . .
H H17 0.303 0.5759 0.1897 0.068 Uiso calc R 1 . .
C C5 1.3760(4) 0.0654(3) -0.2266(3) 0.0698(8) Uani d . 1 . .
H H5 1.3678 0.1278 -0.2966 0.084 Uiso calc R 1 . .
C C14 0.6934(4) 0.1977(3) 0.3619(3) 0.0607(7) Uani d . 1 . .
C C3 1.4975(4) -0.1219(3) -0.1282(4) 0.0744(9) Uani d . 1 . .
H H3 1.5726 -0.1842 -0.1346 0.089 Uiso calc R 1 . .
C C2 1.4015(4) -0.1244(3) -0.0160(4) 0.0731(9) Uani d . 1 . .
H H2 1.4109 -0.1874 0.0533 0.088 Uiso calc R 1 . .
C C4 1.4834(4) -0.0276(3) -0.2318(4) 0.0741(9) Uani d . 1 . .
H H4 1.5492 -0.0284 -0.3063 0.089 Uiso calc R 1 . .
C C21 0.2760(4) 0.7012(4) 0.3487(3) 0.0758(9) Uani d . 1 . .
H H21A 0.2427 0.6714 0.4351 0.114 Uiso calc R 1 . .
H H21B 0.1923 0.6995 0.3194 0.114 Uiso calc R 1 . .
H H21C 0.3147 0.7885 0.3209 0.114 Uiso calc R 1 . .
C C22 0.9462(5) 0.6658(5) 0.6350(3) 0.0891(12) Uani d . 1 . .
H H22 0.9634 0.7143 0.6799 0.107 Uiso calc R 1 . .
C C23 0.8339(7) 0.6759(7) 0.4809(5) 0.129(2) Uani d . 1 . .
H H23A 0.9116 0.6194 0.452 0.193 Uiso calc R 1 . .
H H23B 0.8186 0.7448 0.4138 0.193 Uiso calc R 1 . .
H H23C 0.7414 0.6273 0.5257 0.193 Uiso calc R 1 . .
C C24 0.8343(11) 0.8624(6) 0.5458(6) 0.166(3) Uani d . 1 . .
H H24A 0.8771 0.893 0.594 0.248 Uiso calc R 1 . .
H H24B 0.7259 0.8674 0.5737 0.248 Uiso calc R 1 . .
H H24C 0.8709 0.9153 0.4632 0.248 Uiso calc R 1 . .
N N2 0.9713(2) 0.20712(19) 0.06434(18) 0.0433(5) Uani d . 1 . .
N N1 1.1644(3) 0.1543(2) -0.0946(2) 0.0562(6) Uani d . 1 . .
N N3 1.0040(3) 0.3596(2) -0.12669(19) 0.0514(5) Uani d . 1 . .
H H3A 1.0718 0.3101 -0.1565 0.062 Uiso calc R 1 . .
H H3B 0.9819 0.4317 -0.173 0.062 Uiso calc R 1 . .
N N4 0.7859(3) 0.6322(2) -0.0926(2) 0.0565(6) Uani d . 1 . .
N N6 0.8779(3) 0.7285(2) 0.5554(2) 0.0623(6) Uani d . 1 . .
N N5 0.6240(4) 0.1571(3) 0.4609(2) 0.0887(10) Uani d . 1 . .
O O1 0.9321(3) 0.0643(2) 0.25406(19) 0.0704(6) Uani d . 1 . .
O O2 0.9896(3) 0.5574(3) 0.6592(2) 0.0853(8) Uani d . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 . 1.721(3) ?
S1 C7 . 1.750(2) ?
C8 N3 . 1.309(3) ?
C8 N2 . 1.405(3) ?
C8 C9 . 1.408(4) ?
C10 C11 . 1.377(4) ?
C10 C9 . 1.397(3) ?
C10 C15 . 1.480(4) ?
C12 O1 . 1.220(3) ?
C12 C11 . 1.428(4) ?
C12 N2 . 1.437(3) ?
C9 C13 . 1.433(3) ?
C11 C14 . 1.429(4) ?
C13 N4 . 1.143(3) ?
C7 N1 . 1.303(4) ?
C7 N2 . 1.423(3) ?
C6 N1 . 1.382(4) ?
C6 C5 . 1.391(4) ?
C6 C1 . 1.399(4) ?
C15 C16 . 1.384(4) ?
C15 C20 . 1.402(4) ?
C16 C17 . 1.377(4) ?
C20 C19 . 1.374(4) ?
C1 C2 . 1.404(4) ?
C18 C19 . 1.378(4) ?
C18 C17 . 1.403(4) ?
C18 C21 . 1.496(4) ?
C5 C4 . 1.357(5) ?
C14 N5 . 1.143(4) ?
C3 C2 . 1.380(5) ?
C3 C4 . 1.391(6) ?
C22 O2 . 1.183(5) ?
C22 N6 . 1.309(5) ?
C23 N6 . 1.396(6) ?
C24 N6 . 1.451(6) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 S1 C7 . . 88.21(13) ?
N3 C8 N2 . . 119.6(2) ?
N3 C8 C9 . . 122.2(2) ?
N2 C8 C9 . . 118.1(2) ?
C11 C10 C9 . . 118.3(2) ?
C11 C10 C15 . . 121.5(2) ?
C9 C10 C15 . . 120.1(2) ?
O1 C12 C11 . . 123.8(2) ?
O1 C12 N2 . . 118.6(3) ?
C11 C12 N2 . . 117.6(2) ?
C10 C9 C8 . . 122.9(2) ?
C10 C9 C13 . . 119.7(2) ?
C8 C9 C13 . . 117.3(2) ?
C10 C11 C12 . . 122.2(2) ?
C10 C11 C14 . . 121.6(3) ?
C12 C11 C14 . . 116.2(2) ?
N4 C13 C9 . . 178.2(3) ?
N1 C7 N2 . . 122.1(2) ?
N1 C7 S1 . . 115.8(2) ?
N2 C7 S1 . . 122.02(18) ?
N1 C6 C5 . . 125.6(3) ?
N1 C6 C1 . . 113.8(3) ?
C5 C6 C1 . . 120.6(3) ?
C16 C15 C20 . . 118.3(2) ?
C16 C15 C10 . . 120.1(2) ?
C20 C15 C10 . . 121.6(2) ?
C17 C16 C15 . . 121.0(2) ?
C19 C20 C15 . . 120.0(3) ?
C6 C1 C2 . . 120.0(3) ?
C6 C1 S1 . . 111.1(2) ?
C2 C1 S1 . . 128.9(3) ?
C19 C18 C17 . . 117.1(3) ?
C19 C18 C21 . . 122.5(3) ?
C17 C18 C21 . . 120.3(3) ?
C20 C19 C18 . . 122.4(2) ?
C16 C17 C18 . . 121.2(3) ?
C4 C5 C6 . . 118.8(3) ?
N5 C14 C11 . . 178.4(4) ?
C2 C3 C4 . . 121.0(3) ?
C3 C2 C1 . . 118.1(3) ?
C5 C4 C3 . . 121.5(3) ?
O2 C22 N6 . . 130.5(5) ?
C8 N2 C7 . . 121.8(2) ?
C8 N2 C12 . . 120.7(2) ?
C7 N2 C12 . . 117.4(2) ?
C7 N1 C6 . . 111.1(2) ?
C22 N6 C23 . . 125.7(4) ?
C22 N6 C24 . . 119.0(5) ?
C23 N6 C24 . . 115.1(5) ?

####################################################################### 
# 
# 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_User-defined
_database_code_depnum_ccdc_archive 'CCDC 1858433'
_audit_update_record             
;
2018-07-26 deposited with the CCDC.
2018-10-19 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C20 H10 Cl N5 O S'
_chemical_formula_moiety         'C20 H10 Cl N5 O S'
_chemical_formula_weight         403.84
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.4441(8)
_cell_length_b                   12.3108(13)
_cell_length_c                   12.7473(12)
_cell_angle_alpha                61.344(5)
_cell_angle_beta                 80.031(6)
_cell_angle_gamma                83.005(6)
_cell_volume                     873.13(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4717
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      27.46
_cell_measurement_temperature    150
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412.00
_exptl_absorpt_coefficient_mu    0.361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_T_max  0.930

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      150
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            8558
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3935
_reflns_number_gt                3027
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0968
_refine_ls_number_restraints     7
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3935
_refine_ls_number_parameters     247
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0686P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.26181(7) 1.53902(3) 0.60828(4) 0.03243(13) Uani 1.0 2 d . . .
S1 S 0.25283(6) 0.52271(3) 0.90163(3) 0.02405(11) Uani 1.0 2 d . . .
O1 O 0.07178(17) 0.72970(10) 0.84946(10) 0.0297(3) Uani 1.0 2 d . . .
N1 N 0.6345(2) 0.57714(12) 0.79036(11) 0.0242(3) Uani 1.0 2 d . . .
N2 N 0.4168(2) 0.75718(11) 0.76149(11) 0.0208(3) Uani 1.0 2 d . . .
N3 N 0.7535(2) 0.79729(12) 0.64936(12) 0.0281(3) Uani 1.0 2 d . . .
N4 N 0.8251(3) 1.10783(13) 0.49781(13) 0.0310(4) Uani 1.0 2 d . . .
N5 N -0.1553(3) 0.99013(12) 0.86424(14) 0.0367(4) Uani 1.0 2 d . . .
C1 C 0.4357(3) 0.40258(14) 0.91518(13) 0.0240(4) Uani 1.0 2 d . . .
C2 C 0.4068(3) 0.27496(14) 0.97872(14) 0.0287(4) Uani 1.0 2 d . . .
C3 C 0.5776(3) 0.19671(15) 0.97578(14) 0.0298(4) Uani 1.0 2 d . . .
C4 C 0.7744(3) 0.24270(15) 0.91381(15) 0.0297(4) Uani 1.0 2 d . . .
C5 C 0.8041(3) 0.36811(14) 0.85131(14) 0.0267(4) Uani 1.0 2 d . . .
C6 C 0.6312(3) 0.44889(14) 0.85056(13) 0.0234(4) Uani 1.0 2 d . . .
C7 C 0.4510(3) 0.62609(13) 0.81013(13) 0.0214(3) Uani 1.0 2 d . . .
C8 C 0.5743(3) 0.83959(14) 0.68700(13) 0.0211(3) Uani 1.0 2 d . . .
C9 C 0.5350(3) 0.96680(14) 0.65272(13) 0.0222(4) Uani 1.0 2 d . . .
C10 C 0.3476(3) 1.01307(13) 0.69533(13) 0.0211(3) Uani 1.0 2 d . . .
C11 C 0.1908(3) 0.93106(14) 0.76437(13) 0.0242(3) Uani 1.0 2 d . . .
C12 C 0.2131(3) 0.80215(14) 0.79433(13) 0.0228(4) Uani 1.0 2 d . . .
C13 C 0.6934(3) 1.04791(14) 0.56811(14) 0.0234(4) Uani 1.0 2 d . . .
C14 C -0.0010(3) 0.96591(14) 0.81823(14) 0.0242(3) Uani 1.0 2 d . . .
C15 C 0.3250(3) 1.14404(13) 0.67093(13) 0.0221(4) Uani 1.0 2 d . . .
C16 C 0.4800(3) 1.19253(14) 0.69896(14) 0.0256(4) Uani 1.0 2 d . . .
C17 C 0.4597(3) 1.31354(14) 0.68011(14) 0.0264(4) Uani 1.0 2 d . . .
C18 C 0.2856(3) 1.38650(14) 0.63215(13) 0.0246(4) Uani 1.0 2 d . . .
C19 C 0.1285(3) 1.34046(14) 0.60464(14) 0.0269(4) Uani 1.0 2 d . . .
C20 C 0.1495(3) 1.21920(14) 0.62391(14) 0.0252(4) Uani 1.0 2 d . . .
H2 H 0.2740 0.2433 1.0224 0.0344 Uiso 1.0 2 calc R . .
H3A H 0.7733 0.7177 0.6711 0.0337 Uiso 1.0 2 calc R . .
H3B H 0.8533 0.8486 0.6025 0.0337 Uiso 1.0 2 calc R . .
H3 H 0.5610 0.1098 1.0167 0.0358 Uiso 1.0 2 calc R . .
H4 H 0.8898 0.1864 0.9148 0.0357 Uiso 1.0 2 calc R . .
H5 H 0.9384 0.3990 0.8098 0.0320 Uiso 1.0 2 calc R . .
H16 H 0.6001 1.1420 0.7312 0.0307 Uiso 1.0 2 calc R . .
H17 H 0.5644 1.3461 0.7000 0.0317 Uiso 1.0 2 calc R . .
H19 H 0.0082 1.3913 0.5730 0.0323 Uiso 1.0 2 calc R . .
H20 H 0.0432 1.1869 0.6049 0.0303 Uiso 1.0 2 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Cl1 C18 1.7435(19) yes . .
S1 C1 1.7338(17) yes . .
S1 C7 1.7516(15) yes . .
O1 C12 1.2222(19) yes . .
N1 C6 1.387(2) yes . .
N1 C7 1.301(2) yes . .
N2 C7 1.428(2) yes . .
N2 C8 1.3980(18) yes . .
N2 C12 1.435(2) yes . .
N3 C8 1.317(2) yes . .
N4 C13 1.1501(19) yes . .
N5 C14 1.147(3) yes . .
C1 C2 1.399(3) yes . .
C1 C6 1.399(2) yes . .
C2 C3 1.379(3) yes . .
C3 C4 1.397(3) yes . .
C4 C5 1.376(3) yes . .
C5 C6 1.398(3) yes . .
C8 C9 1.412(3) yes . .
C9 C10 1.407(3) yes . .
C9 C13 1.427(2) yes . .
C10 C11 1.380(2) yes . .
C10 C15 1.482(3) yes . .
C11 C12 1.438(3) yes . .
C11 C14 1.429(3) yes . .
C15 C16 1.398(3) yes . .
C15 C20 1.394(2) yes . .
C16 C17 1.384(3) yes . .
C17 C18 1.380(3) yes . .
C18 C19 1.387(3) yes . .
C19 C20 1.385(3) yes . .
N3 H3A 0.880 no . .
N3 H3B 0.880 no . .
C2 H2 0.950 no . .
C3 H3 0.950 no . .
C4 H4 0.950 no . .
C5 H5 0.950 no . .
C16 H16 0.950 no . .
C17 H17 0.950 no . .
C19 H19 0.950 no . .
C20 H20 0.950 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 S1 C7 87.99(8) yes . . .
C6 N1 C7 110.59(12) yes . . .
C7 N2 C8 122.24(13) yes . . .
C7 N2 C12 117.15(12) yes . . .
C8 N2 C12 120.59(13) yes . . .
S1 C1 C2 128.42(13) yes . . .
S1 C1 C6 110.65(12) yes . . .
C2 C1 C6 120.93(15) yes . . .
C1 C2 C3 117.77(15) yes . . .
C2 C3 C4 121.37(16) yes . . .
C3 C4 C5 121.17(16) yes . . .
C4 C5 C6 118.23(15) yes . . .
N1 C6 C1 114.31(14) yes . . .
N1 C6 C5 125.19(14) yes . . .
C1 C6 C5 120.49(14) yes . . .
S1 C7 N1 116.45(11) yes . . .
S1 C7 N2 122.35(11) yes . . .
N1 C7 N2 121.18(13) yes . . .
N2 C8 N3 119.50(15) yes . . .
N2 C8 C9 118.70(14) yes . . .
N3 C8 C9 121.79(13) yes . . .
C8 C9 C10 122.56(13) yes . . .
C8 C9 C13 116.24(14) yes . . .
C10 C9 C13 121.15(15) yes . . .
C9 C10 C11 117.62(15) yes . . .
C9 C10 C15 120.71(13) yes . . .
C11 C10 C15 121.62(15) yes . . .
C10 C11 C12 122.68(15) yes . . .
C10 C11 C14 122.50(16) yes . . .
C12 C11 C14 114.70(13) yes . . .
O1 C12 N2 119.31(15) yes . . .
O1 C12 C11 123.60(15) yes . . .
N2 C12 C11 117.03(13) yes . . .
N4 C13 C9 175.8(3) yes . . .
N5 C14 C11 177.87(14) yes . . .
C10 C15 C16 119.37(14) yes . . .
C10 C15 C20 121.49(17) yes . . .
C16 C15 C20 119.11(16) yes . . .
C15 C16 C17 120.48(15) yes . . .
C16 C17 C18 119.31(19) yes . . .
Cl1 C18 C17 118.97(16) yes . . .
Cl1 C18 C19 119.57(12) yes . . .
C17 C18 C19 121.45(17) yes . . .
C18 C19 C20 118.98(15) yes . . .
C15 C20 C19 120.67(18) yes . . .
C8 N3 H3A 120.000 no . . .
C8 N3 H3B 119.998 no . . .
H3A N3 H3B 120.001 no . . .
C1 C2 H2 121.116 no . . .
C3 C2 H2 121.114 no . . .
C2 C3 H3 119.316 no . . .
C4 C3 H3 119.317 no . . .
C3 C4 H4 119.412 no . . .
C5 C4 H4 119.421 no . . .
C4 C5 H5 120.888 no . . .
C6 C5 H5 120.886 no . . .
C15 C16 H16 119.754 no . . .
C17 C16 H16 119.767 no . . .
C16 C17 H17 120.346 no . . .
C18 C17 H17 120.348 no . . .
C18 C19 H19 120.515 no . . .
C20 C19 H19 120.505 no . . .
C15 C20 H20 119.667 no . . .
C19 C20 H20 119.662 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 S1 C7 N1 0.50(14) no . . . .
C1 S1 C7 N2 -178.10(15) no . . . .
C7 S1 C1 C2 -179.39(17) no . . . .
C7 S1 C1 C6 0.18(13) no . . . .
C6 N1 C7 S1 -1.0(3) no . . . .
C6 N1 C7 N2 177.59(15) no . . . .
C7 N1 C6 C1 1.2(3) no . . . .
C7 N1 C6 C5 -177.96(16) no . . . .
C7 N2 C8 N3 7.4(3) no . . . .
C7 N2 C8 C9 -173.57(15) no . . . .
C8 N2 C7 S1 -179.02(14) no . . . .
C8 N2 C7 N1 2.4(3) no . . . .
C7 N2 C12 O1 -8.5(3) no . . . .
C7 N2 C12 C11 168.71(14) no . . . .
C12 N2 C7 S1 2.3(3) no . . . .
C12 N2 C7 N1 -176.21(15) no . . . .
C8 N2 C12 O1 172.79(15) no . . . .
C8 N2 C12 C11 -10.0(3) no . . . .
C12 N2 C8 N3 -174.02(15) no . . . .
C12 N2 C8 C9 5.0(3) no . . . .
S1 C1 C2 C3 179.78(13) no . . . .
S1 C1 C6 N1 -0.8(2) no . . . .
S1 C1 C6 C5 178.37(12) no . . . .
C2 C1 C6 N1 178.81(16) no . . . .
C2 C1 C6 C5 -2.0(3) no . . . .
C6 C1 C2 C3 0.2(3) no . . . .
C1 C2 C3 C4 1.4(3) no . . . .
C2 C3 C4 C5 -1.3(3) no . . . .
C3 C4 C5 C6 -0.5(3) no . . . .
C4 C5 C6 N1 -178.83(17) no . . . .
C4 C5 C6 C1 2.1(3) no . . . .
N2 C8 C9 C10 3.2(3) no . . . .
N2 C8 C9 C13 -174.57(14) no . . . .
N3 C8 C9 C10 -177.75(16) no . . . .
N3 C8 C9 C13 4.5(3) no . . . .
C8 C9 C10 C11 -6.0(3) no . . . .
C8 C9 C10 C15 171.40(15) no . . . .
C13 C9 C10 C11 171.70(16) no . . . .
C13 C9 C10 C15 -10.9(3) no . . . .
C9 C10 C11 C12 0.5(3) no . . . .
C9 C10 C11 C14 176.30(14) no . . . .
C9 C10 C15 C16 -51.9(2) no . . . .
C9 C10 C15 C20 130.09(16) no . . . .
C11 C10 C15 C16 125.40(16) no . . . .
C11 C10 C15 C20 -52.7(3) no . . . .
C15 C10 C11 C12 -176.82(14) no . . . .
C15 C10 C11 C14 -1.0(3) no . . . .
C10 C11 C12 O1 -175.67(16) no . . . .
C10 C11 C12 N2 7.2(3) no . . . .
C14 C11 C12 O1 8.2(3) no . . . .
C14 C11 C12 N2 -168.86(14) no . . . .
C10 C15 C16 C17 -178.22(12) no . . . .
C10 C15 C20 C19 178.30(12) no . . . .
C16 C15 C20 C19 0.2(3) no . . . .
C20 C15 C16 C17 -0.1(3) no . . . .
C15 C16 C17 C18 -0.6(3) no . . . .
C16 C17 C18 Cl1 -179.80(12) no . . . .
C16 C17 C18 C19 1.3(3) no . . . .
Cl1 C18 C19 C20 179.93(10) no . . . .
C17 C18 C19 C20 -1.2(3) no . . . .
C18 C19 C20 C15 0.4(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
S1 O1 2.4932(13) no . .
S1 C12 3.0273(17) no . .
O1 N5 3.435(2) no . .
O1 C7 2.6984(19) no . .
O1 C8 3.5586(18) no . .
O1 C10 3.5940(19) no . .
O1 C14 2.731(3) no . .
N1 N3 2.5536(18) no . .
N1 C8 2.849(2) no . .
N2 C6 3.569(2) no . .
N2 C10 2.841(2) no . .
N3 N4 3.406(2) no . .
N3 C7 2.8133(19) no . .
N3 C13 2.743(3) no . .
N4 C8 3.413(2) no . .
N4 C10 3.542(2) no . .
N4 C16 3.554(3) no . .
N5 C10 3.528(2) no . .
N5 C12 3.420(3) no . .
N5 C20 3.4894(19) no . .
C1 C4 2.759(3) no . .
C2 C5 2.828(3) no . .
C3 C6 2.761(3) no . .
C5 C7 3.549(3) no . .
C8 C11 2.809(3) no . .
C9 C12 2.808(2) no . .
C9 C16 3.075(3) no . .
C11 C16 3.589(3) no . .
C11 C20 3.115(3) no . .
C13 C15 2.912(3) no . .
C13 C16 3.050(3) no . .
C14 C15 2.925(2) no . .
C14 C20 3.049(2) no . .
C15 C18 2.768(3) no . .
C16 C19 2.781(3) no . .
C17 C20 2.778(3) no . .
Cl1 C17 3.4842(16) no . 2_686
S1 C6 3.550(2) no . 2_667
O1 N3 3.281(2) no . 1_455
O1 C2 3.449(2) no . 2_567
O1 C4 3.508(3) no . 2_667
N2 N4 3.464(2) no . 2_676
N2 C2 3.515(3) no . 2_667
N3 O1 3.281(2) no . 1_655
N3 N4 3.0276(19) no . 2_776
N3 C20 3.530(3) no . 2_676
N4 N2 3.464(2) no . 2_676
N4 N3 3.0276(19) no . 2_776
N4 N4 3.252(3) no . 2_776
N4 C8 3.581(3) no . 2_676
N4 C12 3.384(3) no . 2_676
N4 C20 3.579(3) no . 1_655
N5 C2 3.344(2) no . 2_567
N5 C3 3.458(3) no . 2_567
N5 C4 3.423(3) no . 1_465
N5 C16 3.380(2) no . 1_455
C1 C7 3.543(3) no . 2_667
C2 O1 3.449(2) no . 2_567
C2 N2 3.515(3) no . 2_667
C2 N5 3.344(2) no . 2_567
C2 C17 3.562(3) no . 1_545
C3 N5 3.458(3) no . 2_567
C3 C11 3.438(3) no . 2_667
C3 C12 3.438(3) no . 2_667
C3 C17 3.518(3) no . 1_545
C4 O1 3.508(3) no . 2_667
C4 N5 3.423(3) no . 1_645
C4 C12 3.504(3) no . 2_667
C4 C14 3.577(3) no . 2_667
C4 C17 3.594(3) no . 1_545
C5 C19 3.599(3) no . 1_645
C6 S1 3.550(2) no . 2_667
C7 C1 3.543(3) no . 2_667
C8 N4 3.581(3) no . 2_676
C8 C13 3.537(3) no . 2_676
C9 C13 3.480(3) no . 2_676
C11 C3 3.438(3) no . 2_667
C12 N4 3.384(3) no . 2_676
C12 C3 3.438(3) no . 2_667
C12 C4 3.504(3) no . 2_667
C13 C8 3.537(3) no . 2_676
C13 C9 3.480(3) no . 2_676
C14 C4 3.577(3) no . 2_667
C16 N5 3.380(2) no . 1_655
C17 Cl1 3.4842(16) no . 2_686
C17 C2 3.562(3) no . 1_565
C17 C3 3.518(3) no . 1_565
C17 C4 3.594(3) no . 1_565
C19 C5 3.599(3) no . 1_465
C20 N3 3.530(3) no . 2_676
C20 N4 3.579(3) no . 1_455
Cl1 H17 2.7948 no . .
Cl1 H19 2.8176 no . .
S1 H2 3.0171 no . .
N1 H3A 1.8677 no . .
N1 H3B 3.3462 no . .
N1 H5 2.7037 no . .
N2 H3A 2.4879 no . .
N2 H3B 3.1462 no . .
N4 H3B 2.8026 no . .
N4 H16 3.2691 no . .
N5 H20 3.1692 no . .
C1 H3 3.2405 no . .
C1 H5 3.2892 no . .
C2 H4 3.2691 no . .
C3 H5 3.2768 no . .
C4 H2 3.2822 no . .
C5 H3 3.2639 no . .
C6 H2 3.2955 no . .
C6 H3A 3.1264 no . .
C6 H4 3.2422 no . .
C7 H3A 2.4705 no . .
C9 H3A 3.1789 no . .
C9 H3B 2.5392 no . .
C9 H16 2.8748 no . .
C10 H16 2.6380 no . .
C10 H20 2.6745 no . .
C11 H20 2.9592 no . .
C13 H3B 2.4047 no . .
C13 H16 2.7806 no . .
C14 H20 2.7754 no . .
C15 H17 3.2738 no . .
C15 H19 3.2738 no . .
C16 H20 3.2655 no . .
C17 H19 3.2689 no . .
C18 H16 3.2428 no . .
C18 H20 3.2469 no . .
C19 H17 3.2689 no . .
C20 H16 3.2655 no . .
H2 H3 2.3355 no . .
H3A H5 3.5547 no . .
H3 H4 2.3292 no . .
H4 H5 2.3308 no . .
H16 H17 2.3352 no . .
H19 H20 2.3372 no . .
Cl1 H5 2.9475 no . 1_465
Cl1 H17 3.4968 no . 2_686
Cl1 H19 2.8695 no . 2_586
S1 H5 3.3288 no . 1_455
O1 H2 2.6124 no . 2_567
O1 H3A 3.2855 no . 1_455
O1 H3B 3.2636 no . 1_455
N3 H20 3.2010 no . 2_676
N4 H3A 3.3071 no . 2_776
N4 H3B 2.2163 no . 2_776
N4 H20 2.6565 no . 1_655
N5 H2 2.6644 no . 2_567
N5 H3 3.1856 no . 1_465
N5 H3 2.8755 no . 2_567
N5 H4 2.8407 no . 1_465
N5 H4 3.2364 no . 2_667
N5 H16 2.4540 no . 1_455
C1 H17 3.0983 no . 1_545
C2 H17 3.2259 no . 1_545
C3 H16 3.4684 no . 1_545
C3 H17 3.1004 no . 1_545
C4 H16 3.4971 no . 1_545
C4 H17 2.9000 no . 1_545
C5 H17 2.7955 no . 1_545
C5 H19 3.4493 no . 1_645
C6 H17 2.8673 no . 1_545
C10 H3 3.3636 no . 2_667
C11 H3 3.2560 no . 2_667
C11 H4 3.5859 no . 2_667
C12 H2 3.5013 no . 2_567
C12 H3B 3.4617 no . 1_455
C13 H3B 3.3066 no . 2_776
C13 H20 3.2098 no . 1_655
C14 H2 2.9498 no . 2_567
C14 H3 3.5883 no . 2_667
C14 H4 3.4381 no . 1_465
C14 H4 3.1631 no . 2_667
C14 H16 3.1401 no . 1_455
C18 H5 2.9416 no . 1_465
C18 H19 3.3912 no . 2_586
C19 H5 3.0560 no . 1_465
C19 H19 3.1013 no . 2_586
C20 H3A 3.4117 no . 2_676
C20 H3B 3.3699 no . 2_676
H2 O1 2.6124 no . 2_567
H2 N5 2.6644 no . 2_567
H2 C12 3.5013 no . 2_567
H2 C14 2.9498 no . 2_567
H2 H4 3.3196 no . 1_455
H2 H5 3.4257 no . 1_455
H3A O1 3.2855 no . 1_655
H3A N4 3.3071 no . 2_776
H3A C20 3.4117 no . 2_676
H3A H20 3.1769 no . 2_676
H3B O1 3.2636 no . 1_655
H3B N4 2.2163 no . 2_776
H3B C12 3.4617 no . 1_655
H3B C13 3.3066 no . 2_776
H3B C20 3.3699 no . 2_676
H3B H20 2.8372 no . 2_676
H3 N5 3.1856 no . 1_645
H3 N5 2.8755 no . 2_567
H3 C10 3.3636 no . 2_667
H3 C11 3.2560 no . 2_667
H3 C14 3.5883 no . 2_667
H3 H3 3.1371 no . 2_657
H3 H16 3.4339 no . 1_545
H3 H16 3.3299 no . 2_667
H4 N5 2.8407 no . 1_645
H4 N5 3.2364 no . 2_667
H4 C11 3.5859 no . 2_667
H4 C14 3.4381 no . 1_645
H4 C14 3.1631 no . 2_667
H4 H2 3.3196 no . 1_655
H4 H16 3.5004 no . 1_545
H4 H17 3.4031 no . 1_545
H5 Cl1 2.9475 no . 1_645
H5 S1 3.3288 no . 1_655
H5 C18 2.9416 no . 1_645
H5 C19 3.0560 no . 1_645
H5 H2 3.4257 no . 1_655
H5 H17 3.2581 no . 1_545
H5 H19 3.0181 no . 1_645
H16 N5 2.4540 no . 1_655
H16 C3 3.4684 no . 1_565
H16 C4 3.4971 no . 1_565
H16 C14 3.1401 no . 1_655
H16 H3 3.4339 no . 1_565
H16 H3 3.3299 no . 2_667
H16 H4 3.5004 no . 1_565
H16 H20 2.9978 no . 1_655
H17 Cl1 3.4968 no . 2_686
H17 C1 3.0983 no . 1_565
H17 C2 3.2259 no . 1_565
H17 C3 3.1004 no . 1_565
H17 C4 2.9000 no . 1_565
H17 C5 2.7955 no . 1_565
H17 C6 2.8673 no . 1_565
H17 H4 3.4031 no . 1_565
H17 H5 3.2581 no . 1_565
H17 H19 3.0047 no . 1_655
H19 Cl1 2.8695 no . 2_586
H19 C5 3.4493 no . 1_465
H19 C18 3.3912 no . 2_586
H19 C19 3.1013 no . 2_586
H19 H5 3.0181 no . 1_465
H19 H17 3.0047 no . 1_455
H19 H19 2.4205 no . 2_586
H20 N3 3.2010 no . 2_676
H20 N4 2.6565 no . 1_455
H20 C13 3.2098 no . 1_455
H20 H3A 3.1769 no . 2_676
H20 H3B 2.8372 no . 2_676
H20 H16 2.9978 no . 1_455

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3A N1 . . . 2.5536(18) 0.880 1.868 133.4 no
N3 H3B N4 . . 2_776 3.0276(19) 0.880 2.216 153.1 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

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

data_I_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1858434'
_audit_update_record             
;
2018-07-26 deposited with the CCDC.
2018-10-19 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            F4
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H9 Cl F N5 O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         421.83

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6752(3)
_cell_length_b                   11.0006(6)
_cell_length_c                   13.2731(8)
_cell_angle_alpha                67.007(3)
_cell_angle_beta                 80.203(3)
_cell_angle_gamma                85.509(3)
_cell_volume                     884.07(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7961
_cell_measurement_theta_min      3.6601
_cell_measurement_theta_max      66.1484
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428

_exptl_absorpt_coefficient_mu    3.321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.48
_exptl_absorpt_correction_T_max  0.80

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              'Incoatec Cu-ImS'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'

_diffrn_measurement_device_type  'Bruker X8 Prospector'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            12731
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_theta_min         4.49
_diffrn_reflns_theta_max         66.14
_diffrn_reflns_theta_full        66.14
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12

_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.
;

_reflns_number_total             2991
_reflns_number_gt                2612
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1405
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_number_reflns         2991
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0847P)²+0.6371P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.429
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2012.4.0.0'
_computing_cell_refinement       'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.24915(13) -0.07270(7) 0.40045(6) 0.0580(3) Uani d . 1 . .
S S1 0.16724(9) 1.02772(6) 0.09140(5) 0.0387(2) Uani d . 1 . .
F F1 -0.1769(3) 1.48745(15) -0.05691(14) 0.0581(5) Uani d . 1 . .
O O1 0.3663(3) 0.81679(18) 0.15792(18) 0.0505(5) Uani d . 1 . .
N N5 0.6340(3) 0.5263(2) 0.1830(2) 0.0508(6) Uani d . 1 . .
N N2 0.0328(3) 0.77717(19) 0.23729(16) 0.0319(4) Uani d . 1 . .
N N4 -0.3243(3) 0.3962(2) 0.49995(19) 0.0453(5) Uani d . 1 . .
N N1 -0.1968(3) 0.9605(2) 0.20003(17) 0.0373(5) Uani d . 1 . .
C C17 0.2117(4) 0.0942(2) 0.3772(2) 0.0407(6) Uani d . 1 . .
C C16 0.0464(4) 0.1604(3) 0.3301(2) 0.0401(6) Uani d . 1 . .
H H16 -0.046 0.1164 0.3118 0.048 Uiso calc R 1 . .
C C15 0.0188(4) 0.2936(3) 0.3104(2) 0.0382(6) Uani d . 1 . .
H H15 -0.0925 0.3389 0.2784 0.046 Uiso calc R 1 . .
C C14 0.1561(3) 0.3598(2) 0.33791(19) 0.0318(5) Uani d . 1 . .
C C10 0.1256(3) 0.5034(2) 0.31185(19) 0.0309(5) Uani d . 1 . .
C C11 0.2739(3) 0.5947(2) 0.24804(19) 0.0331(5) Uani d . 1 . .
C C12 0.2381(3) 0.7340(2) 0.2118(2) 0.0349(5) Uani d . 1 . .
C C7 -0.0140(4) 0.9133(2) 0.1848(2) 0.0338(5) Uani d . 1 . .
C C1 -0.0225(4) 1.1477(3) 0.0718(2) 0.0367(5) Uani d . 1 . .
C C2 -0.0088(4) 1.2826(3) 0.0051(2) 0.0420(6) Uani d . 1 . .
H H2 0.1128 1.3203 -0.0377 0.05 Uiso calc R 1 . .
C C3 -0.1843(5) 1.3560(3) 0.0062(2) 0.0439(6) Uani d . 1 . .
C C19 0.3213(4) 0.2909(3) 0.3853(2) 0.0428(6) Uani d . 1 . .
H H19 0.4143 0.3343 0.4039 0.051 Uiso calc R 1 . .
C C18 0.3493(4) 0.1579(3) 0.4052(2) 0.0474(7) Uani d . 1 . .
H H18 0.4601 0.1119 0.4373 0.057 Uiso calc R 1 . .
C C9 -0.0621(3) 0.5508(2) 0.34880(18) 0.0314(5) Uani d . 1 . .
C C13 -0.2078(4) 0.4625(2) 0.4312(2) 0.0339(5) Uani d . 1 . .
C C8 -0.1135(3) 0.6867(2) 0.31046(19) 0.0317(5) Uani d . 1 . .
C C4 -0.3693(5) 1.3053(3) 0.0679(2) 0.0473(6) Uani d . 1 . .
H H4 -0.4836 1.36 0.0651 0.057 Uiso calc R 1 . .
C C5 -0.3817(4) 1.1730(3) 0.1335(2) 0.0447(6) Uani d . 1 . .
H H5 -0.5045 1.1365 0.1753 0.054 Uiso calc R 1 . .
C C6 -0.2063(4) 1.0943(2) 0.1361(2) 0.0350(5) Uani d . 1 . .
C C20 0.4729(4) 0.5561(2) 0.2110(2) 0.0377(6) Uani d . 1 . .
N N3 -0.2939(3) 0.7290(2) 0.34077(18) 0.0419(5) Uani d . 1 . .
H H3A -0.3221 0.8121 0.3157 0.05 Uiso calc R 1 . .
H H3B -0.3838 0.6735 0.3857 0.05 Uiso calc R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C17 . 1.743(3) ?
S1 C1 . 1.731(3) ?
S1 C7 . 1.759(2) ?
F1 C3 . 1.358(3) ?
O1 C12 . 1.216(3) ?
N5 C20 . 1.142(3) ?
N2 C8 . 1.401(3) ?
N2 C7 . 1.418(3) ?
N2 C12 . 1.444(3) ?
N4 C13 . 1.139(3) ?
N1 C7 . 1.303(3) ?
N1 C6 . 1.385(3) ?
C17 C16 . 1.376(4) ?
C17 C18 . 1.376(4) ?
C16 C15 . 1.386(4) ?
C16 H16 . 0.93 ?
C15 C14 . 1.390(3) ?
C15 H15 . 0.93 ?
C14 C19 . 1.385(4) ?
C14 C10 . 1.484(3) ?
C10 C11 . 1.383(3) ?
C10 C9 . 1.404(3) ?
C11 C12 . 1.429(3) ?
C11 C20 . 1.428(3) ?
C1 C6 . 1.394(3) ?
C1 C2 . 1.401(4) ?
C2 C3 . 1.372(4) ?
C2 H2 . 0.93 ?
C3 C4 . 1.383(4) ?
C19 C18 . 1.385(4) ?
C19 H19 . 0.93 ?
C18 H18 . 0.93 ?
C9 C8 . 1.413(3) ?
C9 C13 . 1.429(3) ?
C8 N3 . 1.312(3) ?
C4 C5 . 1.374(4) ?
C4 H4 . 0.93 ?
C5 C6 . 1.397(4) ?
C5 H5 . 0.93 ?
N3 H3A . 0.86 ?
N3 H3B . 0.86 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 S1 C7 . . 88.07(11) ?
C8 N2 C7 . . 121.9(2) ?
C8 N2 C12 . . 120.6(2) ?
C7 N2 C12 . . 117.46(19) ?
C7 N1 C6 . . 111.0(2) ?
C16 C17 C18 . . 121.0(2) ?
C16 C17 Cl1 . . 119.5(2) ?
C18 C17 Cl1 . . 119.4(2) ?
C17 C16 C15 . . 119.3(2) ?
C17 C16 H16 . . 120.3 ?
C15 C16 H16 . . 120.3 ?
C16 C15 C14 . . 120.6(2) ?
C16 C15 H15 . . 119.7 ?
C14 C15 H15 . . 119.7 ?
C19 C14 C15 . . 119.0(2) ?
C19 C14 C10 . . 121.9(2) ?
C15 C14 C10 . . 119.0(2) ?
C11 C10 C9 . . 117.8(2) ?
C11 C10 C14 . . 122.3(2) ?
C9 C10 C14 . . 119.8(2) ?
C10 C11 C12 . . 122.7(2) ?
C10 C11 C20 . . 122.1(2) ?
C12 C11 C20 . . 115.2(2) ?
O1 C12 C11 . . 124.4(2) ?
O1 C12 N2 . . 118.7(2) ?
C11 C12 N2 . . 116.8(2) ?
N1 C7 N2 . . 121.8(2) ?
N1 C7 S1 . . 115.79(18) ?
N2 C7 S1 . . 122.39(17) ?
C6 C1 C2 . . 120.5(2) ?
C6 C1 S1 . . 110.85(19) ?
C2 C1 S1 . . 128.7(2) ?
C3 C2 C1 . . 116.4(2) ?
C3 C2 H2 . . 121.8 ?
C1 C2 H2 . . 121.8 ?
F1 C3 C2 . . 118.1(2) ?
F1 C3 C4 . . 117.5(3) ?
C2 C3 C4 . . 124.3(3) ?
C18 C19 C14 . . 120.6(2) ?
C18 C19 H19 . . 119.7 ?
C14 C19 H19 . . 119.7 ?
C17 C18 C19 . . 119.5(2) ?
C17 C18 H18 . . 120.3 ?
C19 C18 H18 . . 120.3 ?
C10 C9 C8 . . 122.4(2) ?
C10 C9 C13 . . 120.8(2) ?
C8 C9 C13 . . 116.8(2) ?
N4 C13 C9 . . 176.5(3) ?
N3 C8 N2 . . 119.9(2) ?
N3 C8 C9 . . 121.7(2) ?
N2 C8 C9 . . 118.4(2) ?
C5 C4 C3 . . 119.0(3) ?
C5 C4 H4 . . 120.5 ?
C3 C4 H4 . . 120.5 ?
C4 C5 C6 . . 118.8(3) ?
C4 C5 H5 . . 120.6 ?
C6 C5 H5 . . 120.6 ?
N1 C6 C5 . . 124.7(2) ?
N1 C6 C1 . . 114.3(2) ?
C5 C6 C1 . . 121.0(2) ?
N5 C20 C11 . . 178.3(3) ?
C8 N3 H3A . . 120.0 ?
C8 N3 H3B . . 120.0 ?
H3A N3 H3B . . 120.0 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C18 C17 C16 C15 . . . . 0.3(4) ?
Cl1 C17 C16 C15 . . . . -179.10(19) ?
C17 C16 C15 C14 . . . . -0.2(4) ?
C16 C15 C14 C19 . . . . 0.1(4) ?
C16 C15 C14 C10 . . . . 177.8(2) ?
C19 C14 C10 C11 . . . . 53.8(3) ?
C15 C14 C10 C11 . . . . -123.9(3) ?
C19 C14 C10 C9 . . . . -128.8(3) ?
C15 C14 C10 C9 . . . . 53.5(3) ?
C9 C10 C11 C12 . . . . -4.9(3) ?
C14 C10 C11 C12 . . . . 172.5(2) ?
C9 C10 C11 C20 . . . . 176.9(2) ?
C14 C10 C11 C20 . . . . -5.6(4) ?
C10 C11 C12 O1 . . . . 178.2(2) ?
C20 C11 C12 O1 . . . . -3.6(4) ?
C10 C11 C12 N2 . . . . -4.8(3) ?
C20 C11 C12 N2 . . . . 173.5(2) ?
C8 N2 C12 O1 . . . . -171.9(2) ?
C7 N2 C12 O1 . . . . 8.6(3) ?
C8 N2 C12 C11 . . . . 10.9(3) ?
C7 N2 C12 C11 . . . . -168.6(2) ?
C6 N1 C7 N2 . . . . -177.1(2) ?
C6 N1 C7 S1 . . . . 0.5(3) ?
C8 N2 C7 N1 . . . . -1.7(4) ?
C12 N2 C7 N1 . . . . 177.7(2) ?
C8 N2 C7 S1 . . . . -179.17(17) ?
C12 N2 C7 S1 . . . . 0.3(3) ?
C1 S1 C7 N1 . . . . -0.4(2) ?
C1 S1 C7 N2 . . . . 177.3(2) ?
C7 S1 C1 C6 . . . . 0.11(18) ?
C7 S1 C1 C2 . . . . 178.6(3) ?
C6 C1 C2 C3 . . . . -0.8(4) ?
S1 C1 C2 C3 . . . . -179.18(19) ?
C1 C2 C3 F1 . . . . 179.6(2) ?
C1 C2 C3 C4 . . . . -0.1(4) ?
C15 C14 C19 C18 . . . . -0.1(4) ?
C10 C14 C19 C18 . . . . -177.8(2) ?
C16 C17 C18 C19 . . . . -0.3(4) ?
Cl1 C17 C18 C19 . . . . 179.1(2) ?
C14 C19 C18 C17 . . . . 0.2(4) ?
C11 C10 C9 C8 . . . . 9.2(3) ?
C14 C10 C9 C8 . . . . -168.3(2) ?
C11 C10 C9 C13 . . . . -168.2(2) ?
C14 C10 C9 C13 . . . . 14.3(3) ?
C10 C9 C13 N4 . . . . 127.(4) ?
C8 C9 C13 N4 . . . . -51.(4) ?
C7 N2 C8 N3 . . . . -6.9(3) ?
C12 N2 C8 N3 . . . . 173.7(2) ?
C7 N2 C8 C9 . . . . 172.4(2) ?
C12 N2 C8 C9 . . . . -7.0(3) ?
C10 C9 C8 N3 . . . . 176.0(2) ?
C13 C9 C8 N3 . . . . -6.5(3) ?
C10 C9 C8 N2 . . . . -3.3(3) ?
C13 C9 C8 N2 . . . . 174.3(2) ?
F1 C3 C4 C5 . . . . -179.4(2) ?
C2 C3 C4 C5 . . . . 0.3(4) ?
C3 C4 C5 C6 . . . . 0.5(4) ?
C7 N1 C6 C5 . . . . 179.5(2) ?
C7 N1 C6 C1 . . . . -0.4(3) ?
C4 C5 C6 N1 . . . . 178.7(2) ?
C4 C5 C6 C1 . . . . -1.4(4) ?
C2 C1 C6 N1 . . . . -178.5(2) ?
S1 C1 C6 N1 . . . . 0.1(3) ?
C2 C1 C6 C5 . . . . 1.6(4) ?
S1 C1 C6 C5 . . . . -179.8(2) ?
C10 C11 C20 N5 . . . . -112.(10) ?
C12 C11 C20 N5 . . . . 70.(11) ?

