# Supplementary Information (SI) for RSC Pharmaceutics.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_L3
_database_code_depnum_ccdc_archive 'CCDC 2350919'
loop_
_audit_author_name
_audit_author_address
'Simon Hernandez-Ortega'
;UNAM
Mexico
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2024-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H12 F N3 S'
_chemical_formula_sum            'C17 H12 F N3 S'
_chemical_formula_weight         309.36

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_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                   13.1322(4)
_cell_length_b                   6.0454(2)
_cell_length_c                   19.1953(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.2870(10)
_cell_angle_gamma                90
_cell_volume                     1455.07(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2655
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      23.43

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.462
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.232
_shelx_estimated_absorpt_T_min   0.900
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 0.83
_diffrn_reflns_number            12341
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.673
_diffrn_reflns_theta_max         25.390
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2674
_reflns_number_gt                1910
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 V2012 (Bruker, 2012)'
_computing_cell_refinement       'APEX2 V2012 (Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B  (Bruker, 2012)'
_computing_structure_solution    'SHELXTL  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'SHELXTL  (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL  (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²] 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         2674
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0885
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_restrained_S_all      0.967
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.41998(10) 0.4026(2) 0.09606(7) 0.0358(3) Uani 1 1 d . . . . .
C2 C 0.46700(13) 0.5931(3) 0.08129(9) 0.0370(4) Uani 1 1 d . . . . .
N3 N 0.39917(11) 0.7264(2) 0.03555(8) 0.0417(4) Uani 1 1 d . . . . .
C4 C 0.20197(15) 0.6765(3) -0.02711(10) 0.0490(5) Uani 1 1 d . . . . .
H4 H 0.192348 0.810622 -0.051956 0.059 Uiso 1 1 calc R U . . .
C5 C 0.11823(14) 0.5329(3) -0.03499(10) 0.0508(5) Uani 1 1 d . . . . .
H5 H 0.051260 0.570091 -0.065815 0.061 Uiso 1 1 calc R U . . .
C6 C 0.13195(14) 0.3326(3) 0.00240(10) 0.0479(5) Uani 1 1 d . . . . .
H6 H 0.073800 0.238575 -0.004255 0.057 Uiso 1 1 calc R U . . .
C7 C 0.22891(14) 0.2700(3) 0.04882(9) 0.0420(4) Uani 1 1 d . . . . .
H7 H 0.237674 0.136744 0.074136 0.050 Uiso 1 1 calc R U . . .
C8 C 0.31330(13) 0.4156(3) 0.05610(9) 0.0350(4) Uani 1 1 d . . . . .
C9 C 0.30160(13) 0.6164(3) 0.01899(9) 0.0378(4) Uani 1 1 d . . . . .
S10 S 0.75727(4) 0.84050(9) 0.13823(3) 0.05724(19) Uani 1 1 d . . . . .
C11 C 0.73954(17) 0.6262(4) 0.18965(12) 0.0752(7) Uani 1 1 d . . . . .
H11 H 0.794536 0.572789 0.228641 0.090 Uiso 1 1 calc R U . . .
N12 N 0.64440(13) 0.5398(3) 0.17164(9) 0.0660(5) Uani 1 1 d . . . . .
C13 C 0.57954(13) 0.6504(3) 0.11238(9) 0.0390(4) Uani 1 1 d . . . . .
C14 C 0.62819(13) 0.8181(3) 0.08766(9) 0.0434(5) Uani 1 1 d . . . . .
H14 H 0.594999 0.908429 0.048239 0.052 Uiso 1 1 calc R U . . .
C15 C 0.46574(14) 0.2104(3) 0.14109(9) 0.0416(4) Uani 1 1 d . . . . .
H15A H 0.542872 0.216881 0.153481 0.050 Uiso 1 1 calc R U . . .
H15B H 0.442268 0.076461 0.113076 0.050 Uiso 1 1 calc R U . . .
C16 C 0.43399(13) 0.1997(3) 0.21043(9) 0.0381(4) Uani 1 1 d . . . . .
C17 C 0.45808(14) 0.3716(3) 0.26024(10) 0.0450(5) Uani 1 1 d . . . . .
H17 H 0.494281 0.495952 0.251660 0.054 Uiso 1 1 calc R U . . .
C18 C 0.42759(16) 0.3553(3) 0.32252(10) 0.0522(5) Uani 1 1 d . . . . .
C19 C 0.37359(16) 0.1779(4) 0.33761(11) 0.0605(6) Uani 1 1 d . . . . .
H19 H 0.353292 0.172978 0.380060 0.073 Uiso 1 1 calc R U . . .
C20 C 0.35012(16) 0.0074(4) 0.28860(12) 0.0635(6) Uani 1 1 d . . . . .
H20 H 0.313806 -0.115895 0.297844 0.076 Uiso 1 1 calc R U . . .
C21 C 0.38001(15) 0.0171(3) 0.22532(11) 0.0532(5) Uani 1 1 d . . . . .
H21 H 0.363732 -0.100039 0.192464 0.064 Uiso 1 1 calc R U . . .
F1 F 0.45306(12) 0.5241(2) 0.37130(6) 0.0875(4) 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
N1 C2 1.376(2) . ?
N1 C8 1.385(2) . ?
N1 C15 1.466(2) . ?
C2 N3 1.323(2) . ?
C2 C13 1.462(2) . ?
N3 C9 1.394(2) . ?
C4 C5 1.374(2) . ?
C4 C9 1.392(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.373(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.389(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(2) . ?
S10 C11 1.686(2) . ?
S10 C14 1.6900(18) . ?
C11 N12 1.303(2) . ?
C11 H11 0.9300 . ?
N12 C13 1.375(2) . ?
C13 C14 1.357(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.510(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.384(2) . ?
C16 C21 1.387(2) . ?
C17 C18 1.373(3) . ?
C17 H17 0.9300 . ?
C18 F1 1.358(2) . ?
C18 C19 1.364(3) . ?
C19 C20 1.367(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C8 106.29(13) . . ?
C2 N1 C15 130.89(14) . . ?
C8 N1 C15 122.77(13) . . ?
N3 C2 N1 113.08(14) . . ?
N3 C2 C13 121.76(15) . . ?
N1 C2 C13 125.16(15) . . ?
C2 N3 C9 104.65(14) . . ?
C5 C4 C9 118.38(18) . . ?
C5 C4 H4 120.8 . . ?
C9 C4 H4 120.8 . . ?
C4 C5 C6 121.09(18) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 121.86(17) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C8 116.67(17) . . ?
C6 C7 H7 121.7 . . ?
C8 C7 H7 121.7 . . ?
N1 C8 C7 131.69(16) . . ?
N1 C8 C9 105.80(13) . . ?
C7 C8 C9 122.50(16) . . ?
C4 C9 C8 119.50(16) . . ?
C4 C9 N3 130.32(16) . . ?
C8 C9 N3 110.18(15) . . ?
C11 S10 C14 89.15(10) . . ?
N12 C11 S10 116.17(16) . . ?
N12 C11 H11 121.9 . . ?
S10 C11 H11 121.9 . . ?
C11 N12 C13 109.52(16) . . ?
C14 C13 N12 114.35(16) . . ?
C14 C13 C2 123.95(16) . . ?
N12 C13 C2 121.67(15) . . ?
C13 C14 S10 110.80(14) . . ?
C13 C14 H14 124.6 . . ?
S10 C14 H14 124.6 . . ?
N1 C15 C16 112.42(13) . . ?
N1 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
N1 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C21 118.77(17) . . ?
C17 C16 C15 120.70(15) . . ?
C21 C16 C15 120.52(16) . . ?
C18 C17 C16 118.82(17) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
F1 C18 C19 118.79(19) . . ?
F1 C18 C17 118.10(18) . . ?
C19 C18 C17 123.11(19) . . ?
C18 C19 C20 118.15(19) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 H19 120.9 . . ?
C19 C20 C21 120.47(19) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 120.68(19) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?

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
C8 N1 C2 N3 0.24(18) . . . . ?
C15 N1 C2 N3 177.73(15) . . . . ?
C8 N1 C2 C13 179.47(14) . . . . ?
C15 N1 C2 C13 -3.0(3) . . . . ?
N1 C2 N3 C9 -0.24(18) . . . . ?
C13 C2 N3 C9 -179.50(14) . . . . ?
C9 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C2 N1 C8 C7 178.72(17) . . . . ?
C15 N1 C8 C7 1.0(3) . . . . ?
C2 N1 C8 C9 -0.13(16) . . . . ?
C15 N1 C8 C9 -177.87(14) . . . . ?
C6 C7 C8 N1 -178.30(16) . . . . ?
C6 C7 C8 C9 0.4(2) . . . . ?
C5 C4 C9 C8 -0.7(3) . . . . ?
C5 C4 C9 N3 178.43(16) . . . . ?
N1 C8 C9 C4 179.29(15) . . . . ?
C7 C8 C9 C4 0.3(2) . . . . ?
N1 C8 C9 N3 -0.01(17) . . . . ?
C7 C8 C9 N3 -178.99(15) . . . . ?
C2 N3 C9 C4 -179.05(18) . . . . ?
C2 N3 C9 C8 0.15(18) . . . . ?
C14 S10 C11 N12 0.0(2) . . . . ?
S10 C11 N12 C13 0.1(3) . . . . ?
C11 N12 C13 C14 -0.2(2) . . . . ?
C11 N12 C13 C2 -178.31(17) . . . . ?
N3 C2 C13 C14 -13.0(3) . . . . ?
N1 C2 C13 C14 167.79(16) . . . . ?
N3 C2 C13 N12 164.89(16) . . . . ?
N1 C2 C13 N12 -14.3(3) . . . . ?
N12 C13 C14 S10 0.2(2) . . . . ?
C2 C13 C14 S10 178.29(13) . . . . ?
C11 S10 C14 C13 -0.14(15) . . . . ?
C2 N1 C15 C16 108.91(19) . . . . ?
C8 N1 C15 C16 -73.97(19) . . . . ?
N1 C15 C16 C17 -58.7(2) . . . . ?
N1 C15 C16 C21 121.29(17) . . . . ?
C21 C16 C17 C18 -0.1(2) . . . . ?
C15 C16 C17 C18 179.89(16) . . . . ?
C16 C17 C18 F1 179.15(15) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
F1 C18 C19 C20 -178.88(17) . . . . ?
C17 C18 C19 C20 0.8(3) . . . . ?
C18 C19 C20 C21 -0.5(3) . . . . ?
C19 C20 C21 C16 -0.1(3) . . . . ?
C17 C16 C21 C20 0.4(3) . . . . ?
C15 C16 C21 C20 -179.54(17) . . . . ?

_refine_diff_density_max         0.122
_refine_diff_density_min         -0.277
_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_L1
_database_code_depnum_ccdc_archive 'CCDC 2350920'
loop_
_audit_author_name
_audit_author_address
'Simon Hernandez-Ortega'
;UNAM
Mexico
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2024-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H8 F5 N3 S'
_chemical_formula_weight         381.32

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   17.173(4)
_cell_length_b                   8.1616(18)
_cell_length_c                   10.976(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.871(5)
_cell_angle_gamma                90
_cell_volume                     1534.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1268
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      20.32

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.273
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 0.83
_diffrn_reflns_number            13161
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_av_R_equivalents  0.0851
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.377
_diffrn_reflns_theta_max         25.472
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2837
_reflns_number_gt                1400
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 V2012 (Bruker, 2012)'
_computing_cell_refinement       'APEX2 V2012 (Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B  (Bruker, 2012)'
_computing_structure_solution    'SHELXTL  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'SHELXTL  (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL  (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0544P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0045(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2837
_refine_ls_number_parameters     357
_refine_ls_number_restraints     608
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1392
_refine_ls_wR_factor_gt          0.1121
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.910
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C15 C 0.76469(19) 0.1834(4) 0.6279(3) 0.0527(9) Uani 1 1 d D U . . .
H15A H 0.810245 0.251471 0.618905 0.063 Uiso 1 1 calc R U . A 1
H15B H 0.719650 0.255047 0.628688 0.063 Uiso 1 1 calc R U . A 1
N1 N 0.7740(2) 0.0974(5) 0.7439(3) 0.0495(9) Uani 0.793(3) 1 d D U P B 1
C2 C 0.7241(2) 0.0845(5) 0.8372(4) 0.0511(9) Uani 0.793(3) 1 d D U P B 1
N3 N 0.7531(3) 0.0011(8) 0.9306(4) 0.0531(12) Uani 0.793(3) 1 d D U P B 1
C4 C 0.8818(3) -0.1443(6) 0.9631(5) 0.0620(13) Uani 0.793(3) 1 d D U P B 1
H4 H 0.871767 -0.182989 1.040207 0.074 Uiso 0.793(3) 1 calc R U P B 1
C5 C 0.9497(4) -0.1808(10) 0.9156(7) 0.0716(17) Uani 0.793(3) 1 d D U P B 1
H5 H 0.986574 -0.245376 0.959023 0.086 Uiso 0.793(3) 1 calc R U P B 1
C6 C 0.9647(3) -0.1184(8) 0.7961(6) 0.0745(13) Uani 0.793(3) 1 d D U P B 1
H6 H 1.011441 -0.143916 0.762269 0.089 Uiso 0.793(3) 1 calc R U P B 1
C7 C 0.9095(3) -0.0197(12) 0.7306(5) 0.0655(16) Uani 0.793(3) 1 d D U P B 1
H7 H 0.919179 0.024133 0.654917 0.079 Uiso 0.793(3) 1 calc R U P B 1
C8 C 0.8415(3) 0.0087(6) 0.7824(4) 0.0511(11) Uani 0.793(3) 1 d D U P B 1
C9 C 0.8265(3) -0.0491(5) 0.8978(4) 0.0527(10) Uani 0.793(3) 1 d D U P B 1
S10 S 0.51382(10) 0.2256(3) 0.90469(19) 0.0886(6) Uani 0.793(3) 1 d D U P B 1
C11 C 0.5490(4) 0.3166(10) 0.7815(6) 0.0699(13) Uani 0.793(3) 1 d D U P B 1
H11 H 0.520027 0.392817 0.734659 0.084 Uiso 0.793(3) 1 calc R U P B 1
N12 N 0.6186(3) 0.2739(9) 0.7564(4) 0.0622(14) Uani 0.793(3) 1 d D U P B 1
C13 C 0.6466(3) 0.1552(6) 0.8373(4) 0.0544(9) Uani 0.793(3) 1 d . U P B 1
C14 C 0.5968(3) 0.1144(8) 0.9240(5) 0.0687(14) Uani 0.793(3) 1 d D U P B 1
H14 H 0.607041 0.036703 0.985018 0.082 Uiso 0.793(3) 1 calc R U P B 1
N1A N 0.7372(6) 0.1265(19) 0.7429(9) 0.0512(18) Uani 0.207(3) 1 d D U P B 2
C2A C 0.7728(5) 0.0276(17) 0.8322(9) 0.0524(17) Uani 0.207(3) 1 d D U P B 2
N3A N 0.7298(9) -0.002(3) 0.9228(15) 0.053(2) Uani 0.207(3) 1 d D U P B 2
C4A C 0.6006(10) 0.119(3) 0.9697(14) 0.068(2) Uani 0.207(3) 1 d D U P B 2
H4A H 0.603539 0.084482 1.050574 0.082 Uiso 0.207(3) 1 calc R U P B 2
C5A C 0.5358(10) 0.195(4) 0.922(2) 0.074(2) Uani 0.207(3) 1 d D U P B 2
H5A H 0.488425 0.184486 0.957381 0.089 Uiso 0.207(3) 1 calc R U P B 2
C6A C 0.5427(12) 0.293(4) 0.812(2) 0.071(2) Uani 0.207(3) 1 d D U P B 2
H6A H 0.506157 0.373926 0.790832 0.085 Uiso 0.207(3) 1 calc R U P B 2
C7A C 0.6049(12) 0.264(4) 0.7373(19) 0.063(2) Uani 0.207(3) 1 d D U P B 2
H7A H 0.605136 0.306837 0.658934 0.075 Uiso 0.207(3) 1 calc R U P B 2
C8A C 0.6643(6) 0.170(2) 0.7849(10) 0.0541(19) Uani 0.207(3) 1 d D U P B 2
C9A C 0.6629(6) 0.0936(19) 0.8981(10) 0.0571(19) Uani 0.207(3) 1 d D U P B 2
S10A S 0.9788(4) -0.1666(12) 0.8856(9) 0.0806(19) Uani 0.207(3) 1 d D U P B 2
C11A C 0.9607(9) -0.091(3) 0.7434(12) 0.072(3) Uani 0.207(3) 1 d D U P B 2
H11A H 0.998166 -0.090420 0.685941 0.086 Uiso 0.207(3) 1 calc R U P B 2
N12A N 0.8910(8) -0.033(4) 0.7199(11) 0.064(2) Uani 0.207(3) 1 d D U P B 2
C13A C 0.8482(14) -0.030(3) 0.829(2) 0.0544(9) Uani 0.207(3) 1 d . U P B 2
C14A C 0.8926(8) -0.096(3) 0.9253(10) 0.065(2) Uani 0.207(3) 1 d D U P B 2
H14A H 0.876592 -0.100718 1.004451 0.079 Uiso 0.207(3) 1 calc R U P B 2
C16 C 0.75429(19) 0.0704(4) 0.5198(3) 0.0430(8) Uani 1 1 d . . . . .
C17 C 0.80711(19) 0.0650(4) 0.4321(3) 0.0497(9) Uani 1 1 d . . . . .
C18 C 0.7953(2) -0.0278(4) 0.3273(3) 0.0551(9) Uani 1 1 d . . . . .
C19 C 0.7296(2) -0.1190(4) 0.3102(3) 0.0558(9) Uani 1 1 d . . . . .
C20 C 0.6766(2) -0.1192(4) 0.3965(3) 0.0530(9) Uani 1 1 d . . . . .
C21 C 0.68878(19) -0.0249(4) 0.4982(3) 0.0485(8) Uani 1 1 d . . . . .
F1 F 0.87323(12) 0.1544(2) 0.44438(17) 0.0694(6) Uani 1 1 d . . . . .
F2 F 0.84927(13) -0.0258(3) 0.24390(17) 0.0792(7) Uani 1 1 d . . . . .
F3 F 0.71762(14) -0.2080(3) 0.20775(19) 0.0867(7) Uani 1 1 d . . . . .
F4 F 0.61150(13) -0.2073(3) 0.37755(19) 0.0805(7) Uani 1 1 d . . . . .
F5 F 0.63312(11) -0.0238(2) 0.57867(17) 0.0653(6) 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
C15 N1 1.453(4) . ?
C15 N1A 1.453(6) . ?
C15 C16 1.504(4) . ?
N1 C2 1.383(4) . ?
N1 C8 1.407(6) . ?
C2 N3 1.301(5) . ?
C2 C13 1.450(6) . ?
N3 C9 1.397(6) . ?
C4 C5 1.342(7) . ?
C4 C9 1.388(6) . ?
C5 C6 1.447(8) . ?
C6 C7 1.405(8) . ?
C7 C8 1.353(7) . ?
C8 C9 1.391(6) . ?
S10 C11 1.689(5) . ?
S10 C14 1.691(5) . ?
C11 N12 1.293(6) . ?
N12 C13 1.379(7) . ?
C13 C14 1.363(7) . ?
N1A C2A 1.380(7) . ?
N1A C8A 1.409(8) . ?
C2A N3A 1.300(8) . ?
C2A C13A 1.38(3) . ?
N3A C9A 1.399(9) . ?
C4A C5A 1.348(11) . ?
C4A C9A 1.385(8) . ?
C5A C6A 1.461(12) . ?
C6A C7A 1.408(12) . ?
C7A C8A 1.350(9) . ?
C8A C9A 1.392(8) . ?
S10A C14A 1.673(10) . ?
S10A C11A 1.689(9) . ?
C11A N12A 1.296(11) . ?
N12A C13A 1.45(3) . ?
C13A C14A 1.37(2) . ?
C16 C17 1.367(4) . ?
C16 C21 1.375(4) . ?
C17 F1 1.349(4) . ?
C17 C18 1.381(4) . ?
C18 F2 1.345(3) . ?
C18 C19 1.354(5) . ?
C19 F3 1.343(4) . ?
C19 C20 1.357(5) . ?
C20 F4 1.334(4) . ?
C20 C21 1.360(4) . ?
C21 F5 1.345(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
N1 C15 C16 113.3(3) . . ?
N1A C15 C16 117.5(7) . . ?
C2 N1 C8 106.1(3) . . ?
C2 N1 C15 130.4(3) . . ?
C8 N1 C15 123.5(3) . . ?
N3 C2 N1 113.6(4) . . ?
N3 C2 C13 120.6(4) . . ?
N1 C2 C13 125.8(4) . . ?
C2 N3 C9 104.8(3) . . ?
C5 C4 C9 120.4(5) . . ?
C4 C5 C6 119.1(6) . . ?
C7 C6 C5 120.7(5) . . ?
C8 C7 C6 117.1(5) . . ?
C7 C8 C9 122.8(5) . . ?
C7 C8 N1 132.7(5) . . ?
C9 C8 N1 104.5(4) . . ?
C4 C9 C8 119.9(5) . . ?
C4 C9 N3 129.0(4) . . ?
C8 C9 N3 111.1(4) . . ?
C11 S10 C14 89.6(3) . . ?
N12 C11 S10 116.0(4) . . ?
C11 N12 C13 109.8(5) . . ?
C14 C13 N12 114.4(4) . . ?
C14 C13 C2 121.5(4) . . ?
N12 C13 C2 124.0(4) . . ?
C13 C14 S10 110.2(4) . . ?
C2A N1A C8A 106.0(4) . . ?
C2A N1A C15 130.5(5) . . ?
C8A N1A C15 123.4(5) . . ?
N3A C2A C13A 122.5(11) . . ?
N3A C2A N1A 113.8(5) . . ?
C13A C2A N1A 123.6(11) . . ?
C2A N3A C9A 104.5(5) . . ?
C5A C4A C9A 119.8(8) . . ?
C4A C5A C6A 117.6(9) . . ?
C7A C6A C5A 119.6(9) . . ?
C8A C7A C6A 117.0(8) . . ?
C7A C8A C9A 122.8(7) . . ?
C7A C8A N1A 132.9(6) . . ?
C9A C8A N1A 104.3(5) . . ?
C4A C9A C8A 119.9(6) . . ?
C4A C9A N3A 129.0(6) . . ?
C8A C9A N3A 111.1(5) . . ?
C14A S10A C11A 90.2(4) . . ?
N12A C11A S10A 115.3(7) . . ?
C11A N12A C13A 110.8(11) . . ?
C14A C13A C2A 126.1(19) . . ?
C14A C13A N12A 110.1(17) . . ?
C2A C13A N12A 123.7(17) . . ?
C13A C14A S10A 113.1(12) . . ?
C17 C16 C21 115.7(3) . . ?
C17 C16 C15 121.8(3) . . ?
C21 C16 C15 122.4(3) . . ?
F1 C17 C16 120.4(3) . . ?
F1 C17 C18 117.1(3) . . ?
C16 C17 C18 122.5(3) . . ?
F2 C18 C19 121.2(3) . . ?
F2 C18 C17 119.5(3) . . ?
C19 C18 C17 119.4(3) . . ?
F3 C19 C18 119.5(3) . . ?
F3 C19 C20 120.7(3) . . ?
C18 C19 C20 119.7(3) . . ?
F4 C20 C19 119.1(3) . . ?
F4 C20 C21 120.9(3) . . ?
C19 C20 C21 119.9(3) . . ?
F5 C21 C20 117.8(3) . . ?
F5 C21 C16 119.5(3) . . ?
C20 C21 C16 122.7(3) . . ?

_refine_diff_density_max         0.164
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.045


# start Validation Reply Form
_vrf_PLAT088_L1                  
;
PROBLEM: Poor Data / Parameter Ratio .................... 7.95 Note
RESPONSE: ...parameters refined are a lot because the structure is 
disordered are was modeled in two position and refined anisotropically.
;
# end Validation Reply Form

####################################################################### 
# 
# 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_L2
_database_code_depnum_ccdc_archive 'CCDC 2350921'
loop_
_audit_author_name
_audit_author_address
'Simon Hernandez-Ortega'
;UNAM
Mexico
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2024-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H13 N3 S'
_chemical_formula_sum            'C17 H13 N3 S'
_chemical_formula_weight         291.36

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_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                   17.3372(8)
_cell_length_b                   9.2800(4)
_cell_length_c                   19.3163(8)
_cell_angle_alpha                90
_cell_angle_beta                 113.263(2)
_cell_angle_gamma                90
_cell_volume                     2855.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1942
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      19.42

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.387
_exptl_crystal_size_mid          0.243
_exptl_crystal_size_min          0.066
_exptl_absorpt_coefficient_mu    0.223
_shelx_estimated_absorpt_T_min   0.919
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 0.83
_diffrn_reflns_number            25355
_diffrn_reflns_av_unetI/netI     0.0984
_diffrn_reflns_av_R_equivalents  0.0919
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.028
_diffrn_reflns_theta_max         25.328
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5207
_reflns_number_gt                2249
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'APEX2 V2012 (Bruker, 2012)'
_computing_cell_refinement       'APEX2 V2012 (Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B  (Bruker, 2012)'
_computing_structure_solution    'SHELXTL  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'SHELXTL  (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL  (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0742P)²] 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         5207
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1475
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1725
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_restrained_S_all      0.903
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.33599(17) 0.7249(3) 0.18822(15) 0.0405(7) Uani 1 1 d . . . . .
C2 C 0.4089(2) 0.8050(4) 0.21188(19) 0.0417(9) Uani 1 1 d . . . . .
N3 N 0.43013(18) 0.8583(3) 0.28079(15) 0.0484(8) Uani 1 1 d . . . . .
C4 C 0.3591(3) 0.8274(4) 0.3722(2) 0.0604(11) Uani 1 1 d . . . . .
H4 H 0.398089 0.880221 0.411333 0.072 Uiso 1 1 calc R U . . .
C5 C 0.2914(3) 0.7661(5) 0.3798(2) 0.0678(13) Uani 1 1 d . . . . .
H5 H 0.284333 0.777404 0.424752 0.081 Uiso 1 1 calc R U . . .
C6 C 0.2322(3) 0.6863(4) 0.3213(2) 0.0634(12) Uani 1 1 d . . . . .
H6 H 0.186410 0.646818 0.328165 0.076 Uiso 1 1 calc R U . . .
C7 C 0.2400(2) 0.6650(4) 0.2538(2) 0.0534(10) Uani 1 1 d . . . . .
H7 H 0.200973 0.611434 0.215068 0.064 Uiso 1 1 calc R U . . .
C8 C 0.3090(2) 0.7274(4) 0.24684(19) 0.0414(9) Uani 1 1 d . . . . .
C9 C 0.3685(2) 0.8089(4) 0.30359(19) 0.0465(9) Uani 1 1 d . . . . .
S10 S 0.58258(7) 0.88604(13) 0.13439(7) 0.0767(4) Uani 1 1 d . . . . .
C11 C 0.4899(3) 0.8272(4) 0.0689(2) 0.0650(12) Uani 1 1 d . . . . .
H11 H 0.481723 0.814625 0.018719 0.078 Uiso 1 1 calc R U . . .
N12 N 0.4312(2) 0.8009(3) 0.09272(17) 0.0553(9) Uani 1 1 d . . . . .
C13 C 0.4609(2) 0.8277(4) 0.16898(19) 0.0423(9) Uani 1 1 d . . . . .
C14 C 0.5412(2) 0.8756(4) 0.1999(2) 0.0613(11) Uani 1 1 d . . . . .
H14 H 0.569649 0.899532 0.250416 0.074 Uiso 1 1 calc R U . . .
C15 C 0.2961(2) 0.6397(3) 0.11989(16) 0.0445(10) Uani 1 1 d . . . . .
H15A H 0.277544 0.549175 0.133223 0.053 Uiso 1 1 calc R U . . .
H15B H 0.337690 0.617616 0.099573 0.053 Uiso 1 1 calc R U . . .
C16 C 0.2224(2) 0.7106(4) 0.05941(17) 0.0393(9) Uani 1 1 d . . . . .
C17 C 0.2057(2) 0.8562(4) 0.05905(19) 0.0506(10) Uani 1 1 d . . . . .
H17 H 0.239895 0.914137 0.098526 0.061 Uiso 1 1 calc R U . . .
C18 C 0.1386(3) 0.9163(4) 0.0006(2) 0.0659(12) Uani 1 1 d . . . . .
H18 H 0.128257 1.014494 0.001216 0.079 Uiso 1 1 calc R U . . .
C19 C 0.0871(3) 0.8339(5) -0.0582(2) 0.0677(13) Uani 1 1 d . . . . .
H19 H 0.042048 0.875775 -0.097278 0.081 Uiso 1 1 calc R U . . .
C20 C 0.1025(2) 0.6876(5) -0.0590(2) 0.0658(12) Uani 1 1 d . . . . .
H20 H 0.067988 0.630063 -0.098526 0.079 Uiso 1 1 calc R U . . .
C21 C 0.1700(2) 0.6282(4) -0.00017(18) 0.0513(10) Uani 1 1 d . . . . .
H21 H 0.180448 0.529984 -0.000740 0.062 Uiso 1 1 calc R U . . .
N21 N 0.9372(2) 0.8361(3) 0.28807(16) 0.0563(9) Uani 1 1 d . . . . .
C22 C 0.8736(3) 0.7409(4) 0.2606(3) 0.0697(13) Uani 1 1 d . . . . .
N23 N 0.8620(2) 0.6802(3) 0.19716(17) 0.0573(9) Uani 1 1 d . . . . .
C24 C 0.9505(3) 0.7195(4) 0.1174(2) 0.0655(12) Uani 1 1 d . . . . .
H24 H 0.917484 0.656148 0.080209 0.079 Uiso 1 1 calc R U . . .
C25 C 1.0201(2) 0.7861(4) 0.1081(2) 0.0504(10) Uani 1 1 d . . . . .
H25 H 1.036020 0.768033 0.068216 0.061 Uiso 1 1 calc R U . . .
C26 C 1.0619(2) 0.8845(4) 0.1684(2) 0.0620(11) Uani 1 1 d . . . . .
H26 H 1.106779 0.936468 0.166362 0.074 Uiso 1 1 calc R U . . .
C27 C 1.0412(2) 0.9081(4) 0.2287(2) 0.0578(11) Uani 1 1 d . . . . .
H27 H 1.071977 0.972476 0.266352 0.069 Uiso 1 1 calc R U . . .
C28 C 0.9751(3) 0.8362(4) 0.2327(2) 0.0601(11) Uani 1 1 d . . . . .
C29 C 0.9292(3) 0.7434(4) 0.1788(2) 0.0624(12) Uani 1 1 d . . . . .
S30 S 0.70161(8) 0.59571(16) 0.32750(7) 0.0951(5) Uani 1 1 d . . . . .
C31 C 0.7764(3) 0.6944(5) 0.3917(2) 0.0745(13) Uani 1 1 d . . . . .
H31 H 0.776412 0.709812 0.439245 0.089 Uiso 1 1 calc R U . . .
N32 N 0.8349(2) 0.7492(4) 0.3730(2) 0.0725(11) Uani 1 1 d . . . . .
C33 C 0.8189(3) 0.7055(5) 0.2985(2) 0.0654(12) Uani 1 1 d . . . . .
C34 C 0.7473(3) 0.6186(5) 0.2656(2) 0.0722(13) Uani 1 1 d . . . . .
H34 H 0.728087 0.579879 0.217287 0.087 Uiso 1 1 calc R U . . .
C35 C 0.9734(2) 0.9214(4) 0.35620(18) 0.0507(10) Uani 1 1 d . . . . .
H35A H 0.930928 0.936978 0.376351 0.061 Uiso 1 1 calc R U . . .
H35B H 0.988987 1.014883 0.343303 0.061 Uiso 1 1 calc R U . . .
C36 C 1.0498(2) 0.8543(4) 0.41701(18) 0.0413(9) Uani 1 1 d . . . . .
C37 C 1.0736(2) 0.7134(4) 0.41415(19) 0.0512(10) Uani 1 1 d . . . . .
H37 H 1.041631 0.655749 0.373550 0.061 Uiso 1 1 calc R U . . .
C38 C 1.1438(2) 0.6566(4) 0.4704(2) 0.0562(11) Uani 1 1 d . . . . .
H38 H 1.158840 0.561199 0.467782 0.067 Uiso 1 1 calc R U . . .
C39 C 1.1921(2) 0.7424(5) 0.5310(2) 0.0616(12) Uani 1 1 d . . . . .
H39 H 1.240358 0.705486 0.568510 0.074 Uiso 1 1 calc R U . . .
C40 C 1.1682(3) 0.8814(5) 0.5351(2) 0.0591(11) Uani 1 1 d . . . . .
H40 H 1.199570 0.938569 0.576112 0.071 Uiso 1 1 calc R U . . .
C41 C 1.0978(2) 0.9368(4) 0.47864(18) 0.0502(10) Uani 1 1 d . . . . .
H41 H 1.082103 1.031555 0.481972 0.060 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.379(4) . ?
N1 C8 1.386(4) . ?
N1 C15 1.457(4) . ?
C2 N3 1.328(4) . ?
C2 C13 1.462(5) . ?
N3 C9 1.385(4) . ?
C4 C5 1.364(5) . ?
C4 C9 1.408(5) . ?
C5 C6 1.401(5) . ?
C6 C7 1.376(5) . ?
C7 C8 1.383(5) . ?
C8 C9 1.394(5) . ?
S10 C14 1.686(4) . ?
S10 C11 1.695(4) . ?
C11 N12 1.295(5) . ?
N12 C13 1.378(4) . ?
C13 C14 1.355(5) . ?
C15 C16 1.500(4) . ?
C16 C17 1.382(4) . ?
C16 C21 1.382(4) . ?
C17 C18 1.378(5) . ?
C18 C19 1.368(5) . ?
C19 C20 1.385(5) . ?
C20 C21 1.384(5) . ?
N21 C22 1.347(5) . ?
N21 C35 1.449(4) . ?
N21 C28 1.460(5) . ?
C22 N23 1.291(5) . ?
C22 C33 1.446(6) . ?
N23 C29 1.467(5) . ?
C24 C29 1.393(5) . ?
C24 C25 1.428(5) . ?
C25 C26 1.432(5) . ?
C26 C27 1.364(5) . ?
C27 C28 1.355(5) . ?
C28 C29 1.342(5) . ?
S30 C31 1.669(4) . ?
S30 C34 1.689(4) . ?
C31 N32 1.306(5) . ?
N32 C33 1.413(5) . ?
C33 C34 1.405(5) . ?
C35 C36 1.514(4) . ?
C36 C37 1.378(5) . ?
C36 C41 1.383(4) . ?
C37 C38 1.376(5) . ?
C38 C39 1.390(5) . ?
C39 C40 1.366(5) . ?
C40 C41 1.376(5) . ?

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 N1 C8 106.3(3) . . ?
C2 N1 C15 129.6(3) . . ?
C8 N1 C15 123.8(3) . . ?
N3 C2 N1 112.9(3) . . ?
N3 C2 C13 121.7(3) . . ?
N1 C2 C13 125.4(3) . . ?
C2 N3 C9 104.6(3) . . ?
C5 C4 C9 118.3(4) . . ?
C4 C5 C6 121.4(4) . . ?
C7 C6 C5 121.7(4) . . ?
C6 C7 C8 116.4(4) . . ?
C7 C8 N1 131.1(3) . . ?
C7 C8 C9 123.4(4) . . ?
N1 C8 C9 105.6(3) . . ?
N3 C9 C8 110.7(3) . . ?
N3 C9 C4 130.5(4) . . ?
C8 C9 C4 118.8(4) . . ?
C14 S10 C11 89.0(2) . . ?
N12 C11 S10 116.2(3) . . ?
C11 N12 C13 109.4(3) . . ?
C14 C13 N12 114.5(3) . . ?
C14 C13 C2 123.7(3) . . ?
N12 C13 C2 121.8(3) . . ?
C13 C14 S10 110.8(3) . . ?
N1 C15 C16 114.9(3) . . ?
C17 C16 C21 118.0(3) . . ?
C17 C16 C15 123.1(3) . . ?
C21 C16 C15 118.9(3) . . ?
C18 C17 C16 120.5(4) . . ?
C19 C18 C17 121.1(4) . . ?
C18 C19 C20 119.4(4) . . ?
C19 C20 C21 119.0(4) . . ?
C16 C21 C20 121.9(4) . . ?
C22 N21 C35 135.2(4) . . ?
C22 N21 C28 104.3(3) . . ?
C35 N21 C28 120.4(3) . . ?
N23 C22 N21 117.1(4) . . ?
N23 C22 C33 119.6(4) . . ?
N21 C22 C33 123.2(4) . . ?
C22 N23 C29 102.4(4) . . ?
C29 C24 C25 124.1(4) . . ?
C24 C25 C26 110.7(4) . . ?
C27 C26 C25 125.3(4) . . ?
C28 C27 C26 118.9(4) . . ?
C29 C28 C27 121.8(4) . . ?
C29 C28 N21 105.5(4) . . ?
C27 C28 N21 132.7(4) . . ?
C28 C29 C24 119.1(4) . . ?
C28 C29 N23 110.7(4) . . ?
C24 C29 N23 130.2(4) . . ?
C31 S30 C34 90.7(2) . . ?
N32 C31 S30 118.0(3) . . ?
C31 N32 C33 107.9(4) . . ?
C34 C33 N32 114.1(4) . . ?
C34 C33 C22 122.7(4) . . ?
N32 C33 C22 123.1(4) . . ?
C33 C34 S30 109.2(3) . . ?
N21 C35 C36 114.3(3) . . ?
C37 C36 C41 118.2(3) . . ?
C37 C36 C35 122.9(3) . . ?
C41 C36 C35 118.9(3) . . ?
C36 C37 C38 121.1(3) . . ?
C37 C38 C39 119.7(4) . . ?
C40 C39 C38 119.6(4) . . ?
C39 C40 C41 120.1(4) . . ?
C40 C41 C36 121.3(4) . . ?

_refine_diff_density_max         0.354
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.049

# start Validation Reply Form
_vrf_PLAT230_L2                  
;
PROBLEM: Hirshfeld Test Diff for N23 --C22 . 12.0 s.u.
RESPONSE: ...the distances and st. dev. are in normal values
;
# end Validation Reply Form

