# Supplementary Information (SI) for Chemical Science.
# 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_2247aobp2ga
_database_code_depnum_ccdc_archive 'CCDC 2355274'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt'
;The University of Queensland
Australia
;
_audit_update_record             
;
2024-05-14 deposited with the CCDC.	2024-07-31 downloaded from the CCDC.
;

_audit_creation_date             2022-07-17T19:19:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C26 H19 N5 S'
_chemical_formula_weight         433.52

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.0272(12)
_cell_length_b                   12.4547(8)
_cell_length_c                   14.7177(13)
_cell_angle_alpha                90
_cell_angle_beta                 114.829(11)
_cell_angle_gamma                90
_cell_volume                     2167.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    2429
_cell_measurement_theta_min      4.15
_cell_measurement_theta_max      28.98
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.983

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_orient_matrix_ub_11      -0.053121
_diffrn_orient_matrix_ub_12      0.023303
_diffrn_orient_matrix_ub_13      -0.009262
_diffrn_orient_matrix_ub_21      -0.017742
_diffrn_orient_matrix_ub_22      -0.049055
_diffrn_orient_matrix_ub_23      0.01343
_diffrn_orient_matrix_ub_31      0.021503
_diffrn_orient_matrix_ub_32      0.01723
_diffrn_orient_matrix_ub_33      0.050534
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_number            9220
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.271
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             3812
_reflns_number_gt                2830
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0406P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3812
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_restrained_S_all      1.02
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.044

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
C1 C 0.67437(17) 0.52223(19) 0.07483(15) 0.0277(5) Uani 1 1 d . . . . .
C2 C 0.76494(18) 0.5683(2) 0.06191(16) 0.0351(6) Uani 1 1 d . . . . .
H2 H 0.789771 0.638953 0.085031 0.042 Uiso 1 1 calc R U . . .
C3 C 0.8177(2) 0.5085(2) 0.01451(17) 0.0419(6) Uani 1 1 d . . . . .
H3 H 0.880447 0.53717 0.005583 0.05 Uiso 1 1 calc R U . . .
C4 C 0.7786(2) 0.4072(2) -0.01945(17) 0.0453(7) Uani 1 1 d . . . . .
H4 H 0.813574 0.365065 -0.052334 0.054 Uiso 1 1 calc R U . . .
C5 C 0.6877(2) 0.3678(2) -0.00498(16) 0.0425(6) Uani 1 1 d . . . . .
H5 H 0.660369 0.298036 -0.029235 0.051 Uiso 1 1 calc R U . . .
C6 C 0.62240(16) 0.57986(19) 0.13345(14) 0.0267(5) Uani 1 1 d . . . . .
C7 C 0.62401(17) 0.69903(19) 0.13431(15) 0.0292(5) Uani 1 1 d . . . . .
C8 C 0.64842(17) 0.7552(2) 0.22266(16) 0.0344(6) Uani 1 1 d . . . . .
H8 H 0.66621 0.717366 0.283492 0.041 Uiso 1 1 calc R U . . .
C9 C 0.64671(19) 0.8659(2) 0.22167(19) 0.0436(6) Uani 1 1 d . . . . .
H9 H 0.662665 0.904002 0.282048 0.052 Uiso 1 1 calc R U . . .
C10 C 0.62224(19) 0.9221(2) 0.1345(2) 0.0463(7) Uani 1 1 d . . . . .
H10 H 0.622339 0.99834 0.134913 0.056 Uiso 1 1 calc R U . . .
C11 C 0.5976(2) 0.8671(2) 0.0466(2) 0.0433(6) Uani 1 1 d . . . . .
H11 H 0.579734 0.905493 -0.013981 0.052 Uiso 1 1 calc R U . . .
C12 C 0.59886(18) 0.7560(2) 0.04641(17) 0.0349(6) Uani 1 1 d . . . . .
H12 H 0.582393 0.718384 -0.01429 0.042 Uiso 1 1 calc R U . . .
C13 C 0.53102(16) 0.37871(19) 0.25130(14) 0.0277(5) Uani 1 1 d . . . . .
C14 C 0.45822(17) 0.41300(18) 0.37718(15) 0.0268(5) Uani 1 1 d . . . . .
C15 C 0.34441(17) 0.43808(18) 0.34969(15) 0.0279(5) Uani 1 1 d . . . . .
C16 C 0.27504(18) 0.4916(2) 0.25978(15) 0.0344(6) Uani 1 1 d . . . . .
H16 H 0.305997 0.511797 0.214235 0.041 Uiso 1 1 calc R U . . .
C17 C 0.16547(19) 0.5145(2) 0.23753(17) 0.0422(6) Uani 1 1 d . . . . .
H17 H 0.120748 0.551221 0.177225 0.051 Uiso 1 1 calc R U . . .
C18 C 0.1175(2) 0.4839(2) 0.30355(19) 0.0441(6) Uani 1 1 d . . . . .
H18 H 0.040479 0.500116 0.28728 0.053 Uiso 1 1 calc R U . . .
C19 C 0.17999(19) 0.4320(2) 0.38959(18) 0.0390(6) Uani 1 1 d . . . . .
H19 H 0.14572 0.411126 0.432499 0.047 Uiso 1 1 calc R U . . .
C20 C 0.29632(18) 0.40768(19) 0.41762(16) 0.0299(5) Uani 1 1 d . . . . .
C21 C 0.46424(19) 0.33433(18) 0.52896(15) 0.0307(5) Uani 1 1 d . . . . .
C22 C 0.5276(2) 0.2812(2) 0.62167(17) 0.0407(6) Uani 1 1 d . . . . .
H22 H 0.491363 0.261605 0.663352 0.049 Uiso 1 1 calc R U . . .
C23 C 0.6380(2) 0.2583(2) 0.65107(17) 0.0442(6) Uani 1 1 d . . . . .
H23 H 0.678571 0.223814 0.713605 0.053 Uiso 1 1 calc R U . . .
C24 C 0.6945(2) 0.2849(2) 0.59022(17) 0.0402(6) Uani 1 1 d . . . . .
H24 H 0.772216 0.267675 0.611892 0.048 Uiso 1 1 calc R U . . .
C25 C 0.63783(18) 0.3347(2) 0.50122(16) 0.0335(5) Uani 1 1 d . . . . .
H25 H 0.676498 0.35223 0.460981 0.04 Uiso 1 1 calc R U . . .
C26 C 0.52129(17) 0.36131(18) 0.46702(15) 0.0270(5) Uani 1 1 d . . . . .
N1 N 0.63623(15) 0.42352(17) 0.04173(13) 0.0347(5) Uani 1 1 d . . . . .
N2 N 0.57826(14) 0.53620(15) 0.18881(12) 0.0293(4) Uani 1 1 d . . . . .
N3 N 0.57017(14) 0.42704(15) 0.18967(12) 0.0305(5) Uani 1 1 d . . . . .
H3A H 0.590424 0.387964 0.150109 0.037 Uiso 1 1 calc R U . . .
N4 N 0.50972(14) 0.44538(15) 0.31304(12) 0.0302(4) Uani 1 1 d . . . . .
H4A H 0.52873 0.513309 0.314 0.036 Uiso 1 1 calc R U . . .
N5 N 0.35522(15) 0.35735(16) 0.50490(13) 0.0344(5) Uani 1 1 d . . . . .
S1 S 0.51211(5) 0.24601(5) 0.24651(4) 0.03548(18) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N1 1.339(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.486(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.373(4) . ?
C4 C5 1.379(3) . ?
C5 N1 1.338(3) . ?
C6 N2 1.298(2) . ?
C6 C7 1.484(3) . ?
C7 C12 1.388(3) . ?
C7 C8 1.390(3) . ?
C8 C9 1.380(3) . ?
C9 C10 1.376(3) . ?
C10 C11 1.377(3) . ?
C11 C12 1.384(3) . ?
C13 N4 1.343(3) . ?
C13 N3 1.354(2) . ?
C13 S1 1.668(2) . ?
C14 C26 1.388(3) . ?
C14 C15 1.398(3) . ?
C14 N4 1.427(2) . ?
C15 C16 1.417(3) . ?
C15 C20 1.436(3) . ?
C16 C17 1.354(3) . ?
C17 C18 1.411(3) . ?
C18 C19 1.349(3) . ?
C19 C20 1.426(3) . ?
C20 N5 1.343(3) . ?
C21 N5 1.342(3) . ?
C21 C22 1.427(3) . ?
C21 C26 1.437(3) . ?
C22 C23 1.346(3) . ?
C23 C24 1.417(3) . ?
C24 C25 1.354(3) . ?
C25 C26 1.423(3) . ?
N2 N3 1.364(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.27(19) . . ?
N1 C1 C6 117.70(18) . . ?
C2 C1 C6 119.9(2) . . ?
C3 C2 C1 118.3(2) . . ?
C4 C3 C2 119.4(2) . . ?
C3 C4 C5 118.8(2) . . ?
N1 C5 C4 122.9(2) . . ?
N2 C6 C7 114.96(18) . . ?
N2 C6 C1 126.3(2) . . ?
C7 C6 C1 118.67(18) . . ?
C12 C7 C8 119.1(2) . . ?
C12 C7 C6 120.4(2) . . ?
C8 C7 C6 120.5(2) . . ?
C9 C8 C7 119.8(2) . . ?
C10 C9 C8 120.9(2) . . ?
C9 C10 C11 119.7(2) . . ?
C10 C11 C12 120.0(2) . . ?
C11 C12 C7 120.5(2) . . ?
N4 C13 N3 114.9(2) . . ?
N4 C13 S1 124.91(16) . . ?
N3 C13 S1 120.17(16) . . ?
C26 C14 C15 120.73(17) . . ?
C26 C14 N4 120.45(17) . . ?
C15 C14 N4 118.77(19) . . ?
C14 C15 C16 123.94(18) . . ?
C14 C15 C20 117.34(19) . . ?
C16 C15 C20 118.72(19) . . ?
C17 C16 C15 121.3(2) . . ?
C16 C17 C18 120.3(2) . . ?
C19 C18 C17 120.6(2) . . ?
C18 C19 C20 121.5(2) . . ?
N5 C20 C19 119.13(18) . . ?
N5 C20 C15 123.22(19) . . ?
C19 C20 C15 117.6(2) . . ?
N5 C21 C22 118.34(18) . . ?
N5 C21 C26 123.7(2) . . ?
C22 C21 C26 118.0(2) . . ?
C23 C22 C21 121.1(2) . . ?
C22 C23 C24 121.0(2) . . ?
C25 C24 C23 120.1(2) . . ?
C24 C25 C26 121.0(2) . . ?
C14 C26 C25 124.18(18) . . ?
C14 C26 C21 117.12(18) . . ?
C25 C26 C21 118.70(19) . . ?
C5 N1 C1 118.28(19) . . ?
C6 N2 N3 118.67(17) . . ?
C13 N3 N2 120.10(17) . . ?
C13 N4 C14 124.13(19) . . ?
C21 N5 C20 117.92(17) . . ?



# 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_2248aoap2
_database_code_depnum_ccdc_archive 'CCDC 2355276'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt'
;The University of Queensland
Australia
;
_audit_update_record             
;
2024-05-14 deposited with the CCDC.	2024-07-31 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_2248aoap2           
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: theta limit of dual source diffractometer
;
# Added during the CSD deposition process: Tuesday 14 May 2024 07:33 AM
# end Validation Reply Form


_audit_creation_date             2022-07-20T14:11:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C20 H16 N6 S'
_chemical_formula_weight         372.45

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_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_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8060(5)
_cell_length_b                   9.4077(5)
_cell_length_c                   11.8916(6)
_cell_angle_alpha                109.261(5)
_cell_angle_beta                 101.174(4)
_cell_angle_gamma                101.954(4)
_cell_volume                     872.43(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    3929
_cell_measurement_theta_min      4.11
_cell_measurement_theta_max      61.42
_cell_measurement_wavelength     1.54184

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.858
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.534
_shelx_estimated_absorpt_T_max   0.775

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_orient_matrix_ub_11      0.049425
_diffrn_orient_matrix_ub_12      0.150071
_diffrn_orient_matrix_ub_13      -0.026463
_diffrn_orient_matrix_ub_21      -0.153574
_diffrn_orient_matrix_ub_22      0.040734
_diffrn_orient_matrix_ub_23      0.02632
_diffrn_orient_matrix_ub_31      0.093546
_diffrn_orient_matrix_ub_32      0.093427
_diffrn_orient_matrix_ub_33      0.138164
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_number            5869
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.107
_diffrn_reflns_theta_max         61.596
_diffrn_reflns_theta_full        61.596
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_Friedel_coverage         0
_reflns_number_total             2684
_reflns_number_gt                2490
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0775P)²+0.1919P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2684
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1244
_refine_ls_wR_factor_gt          0.1213
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.057

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'

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
C1 C -0.1597(2) -0.0363(2) 0.11528(16) 0.0273(4) Uani 1 1 d . . . . .
C2 C -0.0586(2) -0.0369(2) 0.22096(18) 0.0327(5) Uani 1 1 d . . . . .
H2 H 0.032686 0.052118 0.269228 0.039 Uiso 1 1 calc R U . . .
N6 N -0.0852(2) -0.1574(2) 0.25669(17) 0.0432(5) Uani 1 1 d . . . . .
C3 C -0.2152(3) -0.2786(3) 0.1855(2) 0.0447(5) Uani 1 1 d . . . . .
H3 H -0.23829 -0.368001 0.20681 0.054 Uiso 1 1 calc R U . . .
C4 C -0.3166(3) -0.2785(2) 0.0823(2) 0.0454(6) Uani 1 1 d . . . . .
H4 H -0.408483 -0.367449 0.035319 0.054 Uiso 1 1 calc R U . . .
C5 C -0.1301(2) 0.0957(2) 0.07272(16) 0.0264(4) Uani 1 1 d . . . . .
C6 C -0.2438(3) 0.0827(3) -0.0434(2) 0.0463(6) Uani 1 1 d . . . . .
H6A H -0.309222 0.154833 -0.022296 0.069 Uiso 1 1 calc R U . . .
H6B H -0.315029 -0.025526 -0.086986 0.069 Uiso 1 1 calc R U . . .
H6C H -0.181878 0.110397 -0.097188 0.069 Uiso 1 1 calc R U . . .
C7 C 0.1647(2) 0.4624(2) 0.17702(16) 0.0247(4) Uani 1 1 d . . . . .
C8 C 0.3912(2) 0.5638(2) 0.36535(15) 0.0220(4) Uani 1 1 d . . . . .
C9 C 0.5347(2) 0.5238(2) 0.36026(16) 0.0239(4) Uani 1 1 d . . . . .
C10 C 0.5424(2) 0.3846(2) 0.26851(17) 0.0288(4) Uani 1 1 d . . . . .
H10 H 0.446395 0.313081 0.207024 0.035 Uiso 1 1 calc R U . . .
C11 C 0.6865(3) 0.3535(3) 0.26855(19) 0.0362(5) Uani 1 1 d . . . . .
H11 H 0.690221 0.259985 0.207489 0.043 Uiso 1 1 calc R U . . .
C12 C 0.8309(3) 0.4593(3) 0.3587(2) 0.0380(5) Uani 1 1 d . . . . .
H12 H 0.930695 0.436141 0.357137 0.046 Uiso 1 1 calc R U . . .
C13 C 0.8291(2) 0.5934(2) 0.44734(18) 0.0327(4) Uani 1 1 d . . . . .
H13 H 0.927469 0.663273 0.506828 0.039 Uiso 1 1 calc R U . . .
C14 C 0.6806(2) 0.6303(2) 0.45195(16) 0.0257(4) Uani 1 1 d . . . . .
C15 C 0.5460(2) 0.8029(2) 0.54229(16) 0.0253(4) Uani 1 1 d . . . . .
C16 C 0.5519(2) 0.9495(2) 0.63330(17) 0.0334(5) Uani 1 1 d . . . . .
H16 H 0.651842 1.015204 0.692788 0.04 Uiso 1 1 calc R U . . .
C17 C 0.4165(3) 0.9957(2) 0.63566(18) 0.0374(5) Uani 1 1 d . . . . .
H17 H 0.422642 1.093256 0.697229 0.045 Uiso 1 1 calc R U . . .
C18 C 0.2656(3) 0.9007(2) 0.54767(19) 0.0363(5) Uani 1 1 d . . . . .
H18 H 0.17217 0.935903 0.550024 0.044 Uiso 1 1 calc R U . . .
C19 C 0.2538(2) 0.7595(2) 0.45992(18) 0.0292(4) Uani 1 1 d . . . . .
H19 H 0.151939 0.696249 0.40201 0.035 Uiso 1 1 calc R U . . .
C20 C 0.3930(2) 0.7058(2) 0.45413(16) 0.0243(4) Uani 1 1 d . . . . .
N1 N -0.2915(2) -0.15863(19) 0.04533(16) 0.0387(4) Uani 1 1 d . . . . .
N2 N -0.00479(17) 0.21362(17) 0.14064(13) 0.0253(4) Uani 1 1 d . . . . .
N3 N 0.03026(18) 0.33884(17) 0.10552(14) 0.0279(4) Uani 1 1 d . . . . .
H3A H -0.032417 0.339511 0.038485 0.034 Uiso 1 1 calc R U . . .
N4 N 0.24224(17) 0.45277(17) 0.28176(13) 0.0238(3) Uani 1 1 d . . . . .
H4A H 0.198865 0.373318 0.300151 0.029 Uiso 1 1 calc R U . . .
N5 N 0.68545(18) 0.76423(18) 0.54286(14) 0.0287(4) Uani 1 1 d . . . . .
S1 S 0.22485(6) 0.61118(5) 0.13373(4) 0.0352(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N1 1.344(2) . ?
C1 C2 1.395(3) . ?
C1 C5 1.482(2) . ?
C2 N6 1.329(3) . ?
N6 C3 1.332(3) . ?
C3 C4 1.371(3) . ?
C4 N1 1.333(3) . ?
C5 N2 1.287(2) . ?
C5 C6 1.492(3) . ?
C7 N4 1.340(2) . ?
C7 N3 1.365(2) . ?
C7 S1 1.6672(18) . ?
C8 C20 1.397(3) . ?
C8 C9 1.398(3) . ?
C8 N4 1.429(2) . ?
C9 C10 1.426(3) . ?
C9 C14 1.431(3) . ?
C10 C11 1.359(3) . ?
C11 C12 1.414(3) . ?
C12 C13 1.357(3) . ?
C13 C14 1.427(3) . ?
C14 N5 1.349(2) . ?
C15 N5 1.350(2) . ?
C15 C16 1.428(3) . ?
C15 C20 1.435(3) . ?
C16 C17 1.353(3) . ?
C17 C18 1.418(3) . ?
C18 C19 1.360(3) . ?
C19 C20 1.424(3) . ?
N2 N3 1.372(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 120.77(17) . . ?
N1 C1 C5 116.03(16) . . ?
C2 C1 C5 123.20(16) . . ?
N6 C2 C1 122.48(18) . . ?
C2 N6 C3 115.99(18) . . ?
N6 C3 C4 122.08(19) . . ?
N1 C4 C3 122.61(19) . . ?
N2 C5 C1 115.94(16) . . ?
N2 C5 C6 125.21(17) . . ?
C1 C5 C6 118.85(15) . . ?
N4 C7 N3 114.89(15) . . ?
N4 C7 S1 123.84(13) . . ?
N3 C7 S1 121.27(13) . . ?
C20 C8 C9 120.63(15) . . ?
C20 C8 N4 120.94(15) . . ?
C9 C8 N4 118.36(15) . . ?
C8 C9 C10 123.49(16) . . ?
C8 C9 C14 117.46(16) . . ?
C10 C9 C14 119.04(16) . . ?
C11 C10 C9 120.37(18) . . ?
C10 C11 C12 120.59(19) . . ?
C13 C12 C11 120.97(18) . . ?
C12 C13 C14 120.53(18) . . ?
N5 C14 C13 118.09(16) . . ?
N5 C14 C9 123.42(16) . . ?
C13 C14 C9 118.50(17) . . ?
N5 C15 C16 118.11(16) . . ?
N5 C15 C20 123.56(16) . . ?
C16 C15 C20 118.32(17) . . ?
C17 C16 C15 120.69(18) . . ?
C16 C17 C18 121.04(18) . . ?
C19 C18 C17 120.36(19) . . ?
C18 C19 C20 120.57(17) . . ?
C8 C20 C19 123.88(16) . . ?
C8 C20 C15 117.10(16) . . ?
C19 C20 C15 119.01(16) . . ?
C4 N1 C1 116.05(17) . . ?
C5 N2 N3 118.78(15) . . ?
C7 N3 N2 118.42(14) . . ?
C7 N4 C8 123.91(14) . . ?
C14 N5 C15 117.68(15) . . ?



# 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_2207aodp
_database_code_depnum_ccdc_archive 'CCDC 2355275'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt'
;The University of Queensland
Australia
;
_audit_update_record             
;
2024-05-14 deposited with the CCDC.	2024-07-31 downloaded from the CCDC.
;

_audit_creation_date             2022-08-02T08:40:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C27 H21 N7 S'
_chemical_formula_weight         475.57

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_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_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5694(5)
_cell_length_b                   8.9780(7)
_cell_length_c                   18.7562(13)
_cell_angle_alpha                83.796(6)
_cell_angle_beta                 89.902(6)
_cell_angle_gamma                65.641(7)
_cell_volume                     1153.07(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    3058
_cell_measurement_theta_min      3.78
_cell_measurement_theta_max      29.07
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.37
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_orient_matrix_ub_11      0.022728
_diffrn_orient_matrix_ub_12      -0.018053
_diffrn_orient_matrix_ub_13      0.03749
_diffrn_orient_matrix_ub_21      0.021375
_diffrn_orient_matrix_ub_22      0.06996
_diffrn_orient_matrix_ub_23      -0.000599
_diffrn_orient_matrix_ub_31      -0.098138
_diffrn_orient_matrix_ub_32      0.04906
_diffrn_orient_matrix_ub_33      0.006661
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_number            7863
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.517
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             4038
_reflns_number_gt                3291
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²+0.2296P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0136(17)
_refine_ls_number_reflns         4038
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1024
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
C1 C 0.4275(3) 0.3802(2) 0.82692(10) 0.0239(5) Uani 1 1 d . . . . .
C2 C 0.5566(3) 0.4069(2) 0.87936(10) 0.0234(5) Uani 1 1 d . . . . .
C3 C 0.7118(3) 0.2752(3) 0.91564(11) 0.0305(5) Uani 1 1 d . . . . .
H3 H 0.742343 0.165638 0.906165 0.037 Uiso 1 1 calc R U . . .
C4 C 0.8207(3) 0.3072(3) 0.96585(11) 0.0363(6) Uani 1 1 d . . . . .
H4 H 0.929388 0.219799 0.990902 0.044 Uiso 1 1 calc R U . . .
C5 C 0.7702(3) 0.4670(3) 0.97922(11) 0.0369(6) Uani 1 1 d . . . . .
H5 H 0.838836 0.491252 1.015331 0.044 Uiso 1 1 calc R U . . .
C6 C 0.6183(3) 0.5908(3) 0.93917(11) 0.0336(5) Uani 1 1 d . . . . .
H6 H 0.586712 0.70126 0.947401 0.04 Uiso 1 1 calc R U . . .
C7 C 0.3608(3) 0.2473(2) 0.84568(10) 0.0247(5) Uani 1 1 d . . . . .
C8 C 0.2873(4) 0.1880(3) 0.79381(12) 0.0415(6) Uani 1 1 d . . . . .
H8 H 0.281321 0.229821 0.74472 0.05 Uiso 1 1 calc R U . . .
C9 C 0.2226(4) 0.0676(3) 0.81360(14) 0.0488(7) Uani 1 1 d . . . . .
H9 H 0.170077 0.026502 0.778476 0.059 Uiso 1 1 calc R U . . .
C10 C 0.2350(3) 0.0078(3) 0.88470(14) 0.0419(6) Uani 1 1 d . . . . .
H10 H 0.193955 -0.076764 0.900013 0.05 Uiso 1 1 calc R U . . .
C11 C 0.3087(3) 0.0744(3) 0.93295(13) 0.0408(6) Uani 1 1 d . . . . .
H11 H 0.315711 0.034153 0.982306 0.049 Uiso 1 1 calc R U . . .
C12 C 0.3471(3) 0.6898(2) 0.68111(10) 0.0248(5) Uani 1 1 d . . . . .
C13 C 0.1005(3) 0.7397(2) 0.59135(10) 0.0222(4) Uani 1 1 d . . . . .
C14 C -0.0622(3) 0.8862(2) 0.60708(10) 0.0219(4) Uani 1 1 d . . . . .
C15 C -0.0853(3) 0.9416(3) 0.67592(11) 0.0284(5) Uani 1 1 d . . . . .
H15 H 0.009446 0.880998 0.713428 0.034 Uiso 1 1 calc R U . . .
C16 C -0.2407(3) 1.0799(3) 0.68917(12) 0.0338(5) Uani 1 1 d . . . . .
H16 H -0.254364 1.114131 0.735822 0.041 Uiso 1 1 calc R U . . .
C17 C -0.3804(3) 1.1721(3) 0.63441(12) 0.0340(5) Uani 1 1 d . . . . .
H17 H -0.486764 1.270194 0.643749 0.041 Uiso 1 1 calc R U . . .
C18 C -0.3650(3) 1.1218(3) 0.56754(11) 0.0302(5) Uani 1 1 d . . . . .
H18 H -0.460727 1.184478 0.530614 0.036 Uiso 1 1 calc R U . . .
C19 C -0.2075(3) 0.9775(2) 0.55360(10) 0.0227(4) Uani 1 1 d . . . . .
C20 C -0.0522(3) 0.7837(2) 0.47051(10) 0.0228(4) Uani 1 1 d . . . . .
C21 C -0.0525(3) 0.7356(3) 0.40138(11) 0.0304(5) Uani 1 1 d . . . . .
H21 H -0.151525 0.802829 0.366272 0.037 Uiso 1 1 calc R U . . .
C22 C 0.0901(3) 0.5925(3) 0.38547(12) 0.0374(6) Uani 1 1 d . . . . .
H22 H 0.089164 0.56001 0.338969 0.045 Uiso 1 1 calc R U . . .
C23 C 0.2381(3) 0.4919(3) 0.43597(12) 0.0353(5) Uani 1 1 d . . . . .
H23 H 0.336308 0.39188 0.423944 0.042 Uiso 1 1 calc R U . . .
C24 C 0.2403(3) 0.5386(2) 0.50273(11) 0.0288(5) Uani 1 1 d . . . . .
H24 H 0.341721 0.470615 0.536859 0.035 Uiso 1 1 calc R U . . .
C25 C 0.0959(3) 0.6849(2) 0.52195(10) 0.0228(4) Uani 1 1 d . . . . .
C26 C 0.8823(3) 0.6299(3) 0.79228(13) 0.0453(6) Uani 1 1 d . . . . .
H26A H 0.770811 0.682332 0.757817 0.068 Uiso 1 1 calc R U . . .
H26B H 0.873146 0.535607 0.820933 0.068 Uiso 1 1 calc R U . . .
H26C H 1.002623 0.592081 0.76632 0.068 Uiso 1 1 calc R U . . .
C27 C 0.8830(4) 0.7475(3) 0.83917(14) 0.0446(6) Uani 1 1 d . . . . .
N1 N 0.5128(2) 0.5636(2) 0.88925(9) 0.0287(4) Uani 1 1 d . . . . .
N2 N 0.3616(2) 0.4668(2) 0.76530(9) 0.0276(4) Uani 1 1 d . . . . .
N3 N 0.4166(2) 0.5910(2) 0.74478(9) 0.0298(4) Uani 1 1 d . . . . .
H3A H 0.497955 0.608094 0.772781 0.036 Uiso 1 1 calc R U . . .
N4 N 0.2447(3) 0.6471(2) 0.63744(9) 0.0305(4) Uani 1 1 d . . . . .
N5 N 0.3711(3) 0.1915(2) 0.91542(9) 0.0335(4) Uani 1 1 d . . . . .
N6 N -0.1958(2) 0.9264(2) 0.48690(8) 0.0254(4) Uani 1 1 d . . . . .
H6A H -0.284535 0.988163 0.453317 0.03 Uiso 1 1 calc R U . . .
N7 N 0.8806(4) 0.8414(3) 0.87600(13) 0.0686(7) Uani 1 1 d . . . . .
S1 S 0.42484(8) 0.84243(6) 0.66348(3) 0.02891(18) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N2 1.295(2) . ?
C1 C7 1.485(3) . ?
C1 C2 1.492(3) . ?
C2 N1 1.340(3) . ?
C2 C3 1.387(3) . ?
C3 C4 1.381(3) . ?
C4 C5 1.375(3) . ?
C5 C6 1.375(3) . ?
C6 N1 1.336(3) . ?
C7 N5 1.340(3) . ?
C7 C8 1.378(3) . ?
C8 C9 1.377(3) . ?
C9 C10 1.371(3) . ?
C10 C11 1.372(3) . ?
C11 N5 1.331(3) . ?
C12 N4 1.316(3) . ?
C12 N3 1.370(2) . ?
C12 S1 1.703(2) . ?
C13 N4 1.315(2) . ?
C13 C14 1.442(3) . ?
C13 C25 1.446(3) . ?
C14 C19 1.404(3) . ?
C14 C15 1.418(3) . ?
C15 C16 1.359(3) . ?
C16 C17 1.399(3) . ?
C17 C18 1.367(3) . ?
C18 C19 1.402(3) . ?
C19 N6 1.369(2) . ?
C20 N6 1.361(2) . ?
C20 C25 1.404(3) . ?
C20 C21 1.410(3) . ?
C21 C22 1.357(3) . ?
C22 C23 1.397(3) . ?
C23 C24 1.365(3) . ?
C24 C25 1.403(3) . ?
C26 C27 1.447(4) . ?
C27 N7 1.140(3) . ?
N2 N3 1.363(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C7 115.22(18) . . ?
N2 C1 C2 125.56(19) . . ?
C7 C1 C2 119.20(17) . . ?
N1 C2 C3 122.67(19) . . ?
N1 C2 C1 116.26(17) . . ?
C3 C2 C1 121.07(19) . . ?
C4 C3 C2 118.4(2) . . ?
C5 C4 C3 119.3(2) . . ?
C6 C5 C4 118.5(2) . . ?
N1 C6 C5 123.4(2) . . ?
N5 C7 C8 121.9(2) . . ?
N5 C7 C1 116.76(18) . . ?
C8 C7 C1 121.35(18) . . ?
C9 C8 C7 119.6(2) . . ?
C10 C9 C8 119.1(2) . . ?
C9 C10 C11 117.7(2) . . ?
N5 C11 C10 124.5(2) . . ?
N4 C12 N3 117.05(19) . . ?
N4 C12 S1 126.99(15) . . ?
N3 C12 S1 115.58(16) . . ?
N4 C13 C14 124.45(18) . . ?
N4 C13 C25 118.12(17) . . ?
C14 C13 C25 117.25(16) . . ?
C19 C14 C15 117.57(17) . . ?
C19 C14 C13 119.89(17) . . ?
C15 C14 C13 122.52(17) . . ?
C16 C15 C14 121.16(19) . . ?
C15 C16 C17 120.3(2) . . ?
C18 C17 C16 120.41(19) . . ?
C17 C18 C19 119.83(19) . . ?
N6 C19 C18 119.33(18) . . ?
N6 C19 C14 119.98(17) . . ?
C18 C19 C14 120.69(18) . . ?
N6 C20 C25 120.32(17) . . ?
N6 C20 C21 119.60(18) . . ?
C25 C20 C21 120.08(18) . . ?
C22 C21 C20 119.4(2) . . ?
C21 C22 C23 121.5(2) . . ?
C24 C23 C22 119.42(19) . . ?
C23 C24 C25 121.34(19) . . ?
C24 C25 C20 118.30(18) . . ?
C24 C25 C13 122.04(18) . . ?
C20 C25 C13 119.60(17) . . ?
N7 C27 C26 179.0(3) . . ?
C6 N1 C2 117.58(18) . . ?
C1 N2 N3 118.29(18) . . ?
N2 N3 C12 120.86(18) . . ?
C13 N4 C12 129.78(18) . . ?
C11 N5 C7 117.3(2) . . ?
C20 N6 C19 122.56(16) . . ?



# 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_2301feaobp_auto
_database_code_depnum_ccdc_archive 'CCDC 2355277'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt'
;The University of Queensland
Australia
;
_audit_update_record             
;
2024-05-14 deposited with the CCDC.	2024-07-31 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_2301feaobp_auto     
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: theta limit of dual source diffractometer
;
# Added during the CSD deposition process: Tuesday 14 May 2024 07:33 AM
# end Validation Reply Form


_audit_creation_date             2024-05-14T16:08:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C27 H20 Cl3 N5 O4'
_chemical_formula_weight         584.83

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_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_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6716(4)
_cell_length_b                   11.4509(7)
_cell_length_c                   15.5455(10)
_cell_angle_alpha                102.548(5)
_cell_angle_beta                 98.148(4)
_cell_angle_gamma                103.294(5)
_cell_volume                     1270.60(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    2423
_cell_measurement_theta_min      4.09
_cell_measurement_theta_max      61.26
_cell_measurement_wavelength     1.54184

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            gold
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.528
_shelx_estimated_absorpt_T_max   0.867

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_orient_matrix_ub_11      -0.014391
_diffrn_orient_matrix_ub_12      0.031993
_diffrn_orient_matrix_ub_13      -0.091568
_diffrn_orient_matrix_ub_21      -0.046958
_diffrn_orient_matrix_ub_22      -0.139153
_diffrn_orient_matrix_ub_23      -0.048418
_diffrn_orient_matrix_ub_31      -0.204872
_diffrn_orient_matrix_ub_32      -0.010071
_diffrn_orient_matrix_ub_33      -0.00398
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_number            9940
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.973
_diffrn_reflns_theta_max         61.76
_diffrn_reflns_theta_full        61.76
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_reflns_Friedel_coverage         0
_reflns_number_total             3925
_reflns_number_gt                2979
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0581P)²+0.5525P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3925
_refine_ls_number_parameters     375
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1444
_refine_ls_wR_factor_gt          0.1289
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.067

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
N N 0.0311 0.018 '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'

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
C1 C 0.4897(4) 0.7358(3) 0.1207(2) 0.0232(7) Uani 1 1 d . . . . .
C2 C 0.3415(4) 0.6919(3) 0.0471(2) 0.0278(7) Uani 1 1 d . . . . .
H2 H 0.363141 0.686967 -0.012107 0.033 Uiso 1 1 calc R U . . .
C3 C 0.1668(4) 0.6561(3) 0.0598(2) 0.0320(8) Uani 1 1 d . . . . .
H3 H 0.067692 0.625409 0.009515 0.038 Uiso 1 1 calc R U . . .
C4 C 0.1331(4) 0.6645(3) 0.1470(2) 0.0327(8) Uani 1 1 d . . . . .
H4 H 0.012165 0.636683 0.156035 0.039 Uiso 1 1 calc R U . . .
C5 C 0.2753(4) 0.7129(3) 0.2181(2) 0.0298(8) Uani 1 1 d . . . . .
H5 H 0.253172 0.721313 0.277413 0.036 Uiso 1 1 calc R U . . .
C6 C 0.6785(4) 0.7740(3) 0.1158(2) 0.0253(7) Uani 1 1 d . . . . .
C7 C 0.5943(4) 0.8112(3) 0.2833(2) 0.0249(7) Uani 1 1 d . . . . .
C8 C 0.7444(4) 0.7513(3) 0.0299(2) 0.0249(7) Uani 1 1 d . . . . .
C9 C 0.6708(5) 0.6433(3) -0.0394(2) 0.0330(8) Uani 1 1 d . . . . .
H9 H 0.57063 0.580955 -0.033726 0.04 Uiso 1 1 calc R U . . .
C10 C 0.7428(5) 0.6264(4) -0.1165(2) 0.0407(9) Uani 1 1 d . . . . .
H10 H 0.689156 0.553447 -0.164215 0.049 Uiso 1 1 calc R U . . .
C11 C 0.8910(5) 0.7139(4) -0.1249(3) 0.0441(10) Uani 1 1 d . . . . .
H11 H 0.941436 0.700755 -0.177433 0.053 Uiso 1 1 calc R U . . .
C12 C 0.9660(5) 0.8210(4) -0.0565(3) 0.0437(10) Uani 1 1 d . . . . .
H12 H 1.068478 0.881727 -0.06204 0.052 Uiso 1 1 calc R U . . .
C13 C 0.8930(5) 0.8407(4) 0.0200(2) 0.0352(8) Uani 1 1 d . . . . .
H13 H 0.944135 0.915559 0.066252 0.042 Uiso 1 1 calc R U . . .
C14 C 0.6628(4) 0.8789(3) 0.4401(2) 0.0279(8) Uani 1 1 d . . . . .
C15 C 0.7218(4) 0.8109(3) 0.4993(2) 0.0284(7) Uani 1 1 d . . . . .
C16 C 0.6685(5) 0.6800(3) 0.4774(3) 0.0376(9) Uani 1 1 d . . . . .
H16 H 0.586987 0.6345 0.422167 0.045 Uiso 1 1 calc R U . . .
C17 C 0.7332(5) 0.6184(4) 0.5350(3) 0.0440(9) Uani 1 1 d . . . . .
H17 H 0.695777 0.530134 0.519945 0.053 Uiso 1 1 calc R U . . .
C18 C 0.8552(5) 0.6845(4) 0.6169(3) 0.0466(10) Uani 1 1 d . . . . .
H18 H 0.899933 0.640243 0.6562 0.056 Uiso 1 1 calc R U . . .
C19 C 0.9098(5) 0.8111(4) 0.6405(2) 0.0381(9) Uani 1 1 d . . . . .
H19 H 0.991406 0.854873 0.696023 0.046 Uiso 1 1 calc R U . . .
C20 C 0.8442(4) 0.8765(3) 0.5818(2) 0.0292(8) Uani 1 1 d . . . . .
C21 C 0.8392(4) 1.0716(3) 0.5507(2) 0.0275(7) Uani 1 1 d . . . . .
C22 C 0.8997(4) 1.2025(3) 0.5780(2) 0.0325(8) Uani 1 1 d . . . . .
H22 H 0.985878 1.243024 0.632647 0.039 Uiso 1 1 calc R U . . .
C23 C 0.8346(5) 1.2704(4) 0.5260(3) 0.0383(9) Uani 1 1 d . . . . .
H23 H 0.875914 1.358499 0.544727 0.046 Uiso 1 1 calc R U . . .
C24 C 0.7057(5) 1.2116(4) 0.4442(3) 0.0398(9) Uani 1 1 d . . . . .
H24 H 0.659588 1.260217 0.40899 0.048 Uiso 1 1 calc R U . . .
C25 C 0.6484(5) 1.0855(4) 0.4163(2) 0.0349(8) Uani 1 1 d . . . . .
H25 H 0.562721 1.046745 0.361265 0.042 Uiso 1 1 calc R U . . .
C26 C 0.7142(4) 1.0102(3) 0.4680(2) 0.0296(8) Uani 1 1 d . . . . .
N1 N 0.4511(3) 0.7500(2) 0.20554(17) 0.0235(6) Uani 1 1 d . . . . .
N2 N 0.8051(3) 0.8345(3) 0.18880(18) 0.0284(6) Uani 1 1 d . . . . .
N3 N 0.7641(3) 0.8576(3) 0.27083(18) 0.0283(6) Uani 1 1 d . . . . .
N4 N 0.5462(4) 0.8146(3) 0.35983(18) 0.0333(7) Uani 1 1 d . . . . .
N5 N 0.9015(3) 1.0033(3) 0.60314(18) 0.0283(6) Uani 1 1 d . . . . .
H5A H 0.982507 1.04241 0.653124 0.034 Uiso 1 1 calc R U . . .
Cl1A Cl 0.75328(12) 0.47136(8) 0.24807(6) 0.0397(3) Uani 1 1 d . . . . .
O1 O 0.9393(4) 0.5163(3) 0.2931(2) 0.0765(10) Uani 1 1 d . . . . .
O2 O 0.6390(8) 0.4207(5) 0.3030(3) 0.0829(16) Uani 0.922(12) 1 d . . P A 1
O3 O 0.7381(5) 0.3763(5) 0.1696(2) 0.0680(17) Uani 0.922(12) 1 d . . P A 1
O4 O 0.6970(7) 0.5716(4) 0.2262(5) 0.0935(18) Uani 0.922(12) 1 d . . P A 1
O2' O 0.630(6) 0.544(5) 0.256(3) 0.049(13) Uiso 0.078(12) 1 d . . P A 2
O3' O 0.761(5) 0.457(5) 0.156(3) 0.046(13) Uiso 0.078(12) 1 d . . P A 2
O4' O 0.688(5) 0.374(4) 0.278(3) 0.043(12) Uiso 0.078(12) 1 d . . P A 2
C1B C 0.4568(6) 0.1230(4) 0.1699(4) 0.0574(12) Uani 1 1 d . . . . .
H1B1 H 0.556554 0.16593 0.223017 0.069 Uiso 0.581(6) 1 d R U P B .
H1B2 H 0.402248 0.185972 0.150775 0.069 Uiso 0.581(6) 1 d R U P . .
H1B3 H 0.409347 0.135382 0.110906 0.069 Uiso 0.419(6) 1 d R U P . .
H1B4 H 0.486837 0.203606 0.215622 0.069 Uiso 0.419(6) 1 d R U P . .
Cl1B Cl 0.28933(14) 0.01374(10) 0.19833(7) 0.0545(3) Uani 1 1 d . . . . .
Cl2B Cl 0.6472(3) 0.0741(2) 0.1653(2) 0.0683(11) Uani 0.581(6) 1 d . . P B 1
Cl2C Cl 0.5493(7) 0.0447(3) 0.0780(4) 0.106(2) Uani 0.419(6) 1 d . . P B 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N1 1.376(4) . ?
C1 C2 1.404(4) . ?
C1 C6 1.431(5) . ?
C2 C3 1.365(5) . ?
C3 C4 1.402(5) . ?
C4 C5 1.354(5) . ?
C5 N1 1.373(4) . ?
C6 N2 1.322(4) . ?
C6 C8 1.485(5) . ?
C7 N4 1.290(4) . ?
C7 N3 1.347(4) . ?
C7 N1 1.435(4) . ?
C8 C9 1.391(5) . ?
C8 C13 1.397(5) . ?
C9 C10 1.385(5) . ?
C10 C11 1.374(6) . ?
C11 C12 1.379(6) . ?
C12 C13 1.383(5) . ?
C14 N4 1.372(4) . ?
C14 C26 1.414(5) . ?
C14 C15 1.419(5) . ?
C15 C16 1.409(5) . ?
C15 C20 1.417(5) . ?
C16 C17 1.363(6) . ?
C17 C18 1.410(6) . ?
C18 C19 1.363(6) . ?
C19 C20 1.410(5) . ?
C20 N5 1.366(5) . ?
C21 N5 1.358(4) . ?
C21 C22 1.410(5) . ?
C21 C26 1.419(5) . ?
C22 C23 1.358(5) . ?
C23 C24 1.420(6) . ?
C24 C25 1.360(6) . ?
C25 C26 1.424(5) . ?
N2 N3 1.342(4) . ?
Cl1A O4' 1.32(4) . ?
Cl1A O2' 1.40(4) . ?
Cl1A O4 1.405(4) . ?
Cl1A O3 1.418(3) . ?
Cl1A O3' 1.42(4) . ?
Cl1A O1 1.419(3) . ?
Cl1A O2 1.424(4) . ?
C1B Cl2B 1.685(5) . ?
C1B Cl1B 1.753(4) . ?
C1B Cl2C 1.836(6) . ?
Cl2C Cl2C 2.356(12) 2_655 ?

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 C1 C2 117.6(3) . . ?
N1 C1 C6 116.5(3) . . ?
C2 C1 C6 125.8(3) . . ?
C3 C2 C1 120.6(3) . . ?
C2 C3 C4 120.2(3) . . ?
C5 C4 C3 119.1(3) . . ?
C4 C5 N1 120.9(3) . . ?
N2 C6 C1 121.0(3) . . ?
N2 C6 C8 115.9(3) . . ?
C1 C6 C8 123.0(3) . . ?
N4 C7 N3 126.0(3) . . ?
N4 C7 N1 115.5(3) . . ?
N3 C7 N1 118.5(3) . . ?
C9 C8 C13 118.5(3) . . ?
C9 C8 C6 123.3(3) . . ?
C13 C8 C6 118.2(3) . . ?
C10 C9 C8 120.3(3) . . ?
C11 C10 C9 120.7(4) . . ?
C10 C11 C12 119.6(3) . . ?
C11 C12 C13 120.4(4) . . ?
C12 C13 C8 120.5(4) . . ?
N4 C14 C26 121.8(3) . . ?
N4 C14 C15 118.6(3) . . ?
C26 C14 C15 119.5(3) . . ?
C16 C15 C20 118.8(3) . . ?
C16 C15 C14 122.3(3) . . ?
C20 C15 C14 118.9(3) . . ?
C17 C16 C15 120.3(3) . . ?
C16 C17 C18 120.5(4) . . ?
C19 C18 C17 120.9(4) . . ?
C18 C19 C20 119.4(3) . . ?
N5 C20 C19 120.2(3) . . ?
N5 C20 C15 119.7(3) . . ?
C19 C20 C15 120.1(3) . . ?
N5 C21 C22 120.1(3) . . ?
N5 C21 C26 119.5(3) . . ?
C22 C21 C26 120.4(3) . . ?
C23 C22 C21 119.9(3) . . ?
C22 C23 C24 120.9(4) . . ?
C25 C24 C23 119.8(4) . . ?
C24 C25 C26 121.3(3) . . ?
C14 C26 C21 119.2(3) . . ?
C14 C26 C25 123.2(3) . . ?
C21 C26 C25 117.6(3) . . ?
C5 N1 C1 121.4(3) . . ?
C5 N1 C7 118.4(3) . . ?
C1 N1 C7 120.1(3) . . ?
C6 N2 N3 121.8(3) . . ?
N2 N3 C7 121.2(3) . . ?
C7 N4 C14 122.5(3) . . ?
C21 N5 C20 123.0(3) . . ?
O4' Cl1A O2' 107(3) . . ?
O4 Cl1A O3 111.1(3) . . ?
O4' Cl1A O3' 120(3) . . ?
O2' Cl1A O3' 100(2) . . ?
O4' Cl1A O1 104.2(16) . . ?
O2' Cl1A O1 122.4(19) . . ?
O4 Cl1A O1 107.9(3) . . ?
O3 Cl1A O1 108.8(2) . . ?
O3' Cl1A O1 104.1(15) . . ?
O4 Cl1A O2 108.9(3) . . ?
O3 Cl1A O2 108.3(3) . . ?
O1 Cl1A O2 111.8(3) . . ?
Cl2B C1B Cl1B 110.3(3) . . ?
Cl1B C1B Cl2C 109.8(3) . . ?
C1B Cl2C Cl2C 136.9(4) . 2_655 ?

####################################################################### 
# 
# 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_2409ZnAOAPz
_database_code_depnum_ccdc_archive 'CCDC 2359500'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt'
;The University of Queensland
Australia
;
_audit_update_record             
;
2024-05-31 deposited with the CCDC.	2024-07-31 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT420_2409ZnAOAPz         
;
PROBLEM: D-H Bond Without Acceptor  O2       --H2       .     Please Check
RESPONSE: O2 part of disordered EtOH molecule
;
# Added during the CSD deposition process: Friday 31 May 2024 02:22 AM
# end Validation Reply Form


_audit_creation_date             2024-05-31T11:16:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C40 H30 N12 S2 Zn, C H4 O, C2 H6 O'
_chemical_formula_sum            'C43 H40 N12 O2 S2 Zn'
_chemical_formula_weight         886.36

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_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_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.7994(5)
_cell_length_b                   13.0450(5)
_cell_length_c                   13.6798(6)
_cell_angle_alpha                100.070(2)
_cell_angle_beta                 99.897(2)
_cell_angle_gamma                103.258(2)
_cell_volume                     2134.75(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9934
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      68.38
_cell_measurement_wavelength     1.54184

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2016/2 - Bruker AXS area detector scaling and absorption correcti
;
_exptl_absorpt_correction_T_min  0.635
_exptl_absorpt_correction_T_max  0.753
_shelx_estimated_absorpt_T_min   0.567
_shelx_estimated_absorpt_T_max   0.939

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source_type              'INCOATEC I\mS DIAMONDII'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'PHOTON III CPAD'
_diffrn_orient_matrix_ub_11      -0.014388
_diffrn_orient_matrix_ub_12      0.012779
_diffrn_orient_matrix_ub_13      -0.070459
_diffrn_orient_matrix_ub_21      0.021673
_diffrn_orient_matrix_ub_22      -0.066775
_diffrn_orient_matrix_ub_23      -0.026199
_diffrn_orient_matrix_ub_31      -0.078087
_diffrn_orient_matrix_ub_32      -0.043663
_diffrn_orient_matrix_ub_33      -0.012038
_diffrn_measurement_device       'KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_number            34059
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.365
_diffrn_reflns_theta_max         65
_diffrn_reflns_theta_full        65
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_coverage         0
_reflns_number_total             7221
_reflns_number_gt                6629
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.40B integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0629P)²+4.2011P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7221
_refine_ls_number_parameters     554
_refine_ls_number_restraints     4
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1319
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.282
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.079

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
Zn Zn -1.5491 0.6778 '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'

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
C1A C 0.6239(2) 0.8983(2) 0.4745(2) 0.0244(6) Uani 1 1 d . . . . .
C1B C 0.4346(3) 0.7535(3) 0.1783(2) 0.0314(7) Uani 1 1 d . . . . .
H1B H 0.484158 0.823024 0.189493 0.038 Uiso 1 1 calc R U . . .
C2A C 0.6097(3) 0.9698(3) 0.5569(2) 0.0333(7) Uani 1 1 d . . . . .
H2A H 0.642508 1.044893 0.566231 0.04 Uiso 1 1 calc R U . . .
C2B C 0.3368(3) 0.7262(3) 0.1052(3) 0.0365(8) Uani 1 1 d . . . . .
H2B H 0.321373 0.777747 0.067656 0.044 Uiso 1 1 calc R U . . .
C4A C 0.5090(3) 0.8298(3) 0.6078(2) 0.0384(8) Uani 1 1 d . . . . .
H4A H 0.467304 0.802607 0.653305 0.046 Uiso 1 1 calc R U . . .
C4B C 0.2903(3) 0.5612(3) 0.1416(2) 0.0332(7) Uani 1 1 d . . . . .
H4B H 0.240182 0.491995 0.130446 0.04 Uiso 1 1 calc R U . . .
C5A C 0.5237(2) 0.7574(3) 0.5275(2) 0.0311(7) Uani 1 1 d . . . . .
H5A H 0.493657 0.682133 0.520364 0.037 Uiso 1 1 calc R U . . .
C5B C 0.3878(2) 0.5868(2) 0.2152(2) 0.0229(6) Uani 1 1 d . . . . .
C6A C 0.6883(2) 0.9338(2) 0.4009(2) 0.0238(6) Uani 1 1 d . . . . .
C6B C 0.4191(2) 0.5086(2) 0.2730(2) 0.0230(6) Uani 1 1 d . . . . .
C7A C 0.7617(2) 0.8003(2) 0.1951(2) 0.0224(6) Uani 1 1 d . . . . .
C7B C 0.6577(2) 0.4976(2) 0.4244(2) 0.0240(6) Uani 1 1 d . . . . .
C8A C 0.7420(3) 1.0503(3) 0.4101(3) 0.0368(8) Uani 1 1 d . . . . .
H8A1 H 0.79564 1.05695 0.366761 0.055 Uiso 1 1 d R U . . .
H8A2 H 0.779626 1.083767 0.481062 0.055 Uiso 1 1 d R U . . .
H8A3 H 0.686034 1.08684 0.388404 0.055 Uiso 1 1 d R U . . .
C8B C 0.3385(3) 0.4041(3) 0.2695(3) 0.0375(8) Uani 1 1 d . . . . .
H8B1 H 0.374492 0.362467 0.310837 0.056 Uiso 1 1 d R U . . .
H8B2 H 0.312194 0.362619 0.198942 0.056 Uiso 1 1 d R U . . .
H8B3 H 0.275956 0.418854 0.296507 0.056 Uiso 1 1 d R U . . .
C9A C 0.8684(2) 0.9313(2) 0.1146(2) 0.0234(6) Uani 1 1 d . . . . .
C9B C 0.7853(2) 0.3933(2) 0.4612(2) 0.0234(6) Uani 1 1 d . . . . .
C10A C 0.9539(2) 1.0051(2) 0.1896(2) 0.0241(6) Uani 1 1 d . . . . .
C10B C 0.8260(2) 0.3367(2) 0.5369(2) 0.0241(6) Uani 1 1 d . . . . .
C11A C 0.9961(2) 0.9847(3) 0.2855(2) 0.0293(7) Uani 1 1 d . . . . .
H11A H 0.962768 0.919371 0.302733 0.035 Uiso 1 1 calc R U . . .
C11B C 0.7639(3) 0.3039(2) 0.6066(2) 0.0286(6) Uani 1 1 d . . . . .
H11B H 0.692414 0.3146 0.602101 0.034 Uiso 1 1 calc R U . . .
C12A C 1.0838(3) 1.0576(3) 0.3529(2) 0.0369(8) Uani 1 1 d . . . . .
H12A H 1.110641 1.042694 0.416607 0.044 Uiso 1 1 calc R U . . .
C12B C 0.8052(3) 0.2564(3) 0.6815(2) 0.0370(8) Uani 1 1 d . . . . .
H12B H 0.761684 0.232853 0.72718 0.044 Uiso 1 1 calc R U . . .
C13A C 1.1351(3) 1.1553(3) 0.3286(3) 0.0394(8) Uani 1 1 d . . . . .
H13A H 1.197118 1.204752 0.37538 0.047 Uiso 1 1 calc R U . . .
C13B C 0.9110(3) 0.2429(3) 0.6900(3) 0.0386(8) Uani 1 1 d . . . . .
H13B H 0.939872 0.211669 0.742639 0.046 Uiso 1 1 calc R U . . .
C14A C 1.0958(3) 1.1785(3) 0.2387(2) 0.0332(7) Uani 1 1 d . . . . .
H14A H 1.130045 1.244974 0.223911 0.04 Uiso 1 1 calc R U . . .
C14B C 0.9742(3) 0.2741(3) 0.6234(2) 0.0347(7) Uani 1 1 d . . . . .
H14B H 1.046366 0.264792 0.630021 0.042 Uiso 1 1 calc R U . . .
C15A C 1.0044(2) 1.1052(2) 0.1662(2) 0.0251(6) Uani 1 1 d . . . . .
C15B C 0.9310(2) 0.3203(2) 0.5449(2) 0.0263(6) Uani 1 1 d . . . . .
C16A C 0.8870(2) 1.0617(2) 0.0077(2) 0.0249(6) Uani 1 1 d . . . . .
C16B C 0.9541(2) 0.3902(2) 0.3965(2) 0.0258(6) Uani 1 1 d . . . . .
C17A C 0.8497(3) 1.0908(3) -0.0853(2) 0.0322(7) Uani 1 1 d . . . . .
H17A H 0.885609 1.158436 -0.096963 0.039 Uiso 1 1 calc R U . . .
C17B C 1.0204(3) 0.4121(3) 0.3271(3) 0.0343(7) Uani 1 1 d . . . . .
H17B H 1.092791 0.403191 0.338606 0.041 Uiso 1 1 calc R U . . .
C18A C 0.7635(3) 1.0232(3) -0.1574(3) 0.0378(8) Uani 1 1 d . . . . .
H18A H 0.739671 1.044084 -0.218769 0.045 Uiso 1 1 calc R U . . .
C18B C 0.9809(3) 0.4463(3) 0.2428(3) 0.0418(8) Uani 1 1 d . . . . .
H18B H 1.02632 0.461407 0.196176 0.05 Uiso 1 1 calc R U . . .
C19A C 0.7086(3) 0.9215(3) -0.1420(3) 0.0383(8) Uani 1 1 d . . . . .
H19A H 0.647965 0.875371 -0.192856 0.046 Uiso 1 1 calc R U . . .
C19B C 0.8748(3) 0.4593(3) 0.2245(3) 0.0415(8) Uani 1 1 d . . . . .
H19B H 0.846964 0.480268 0.164323 0.05 Uiso 1 1 calc R U . . .
C20A C 0.7422(3) 0.8895(3) -0.0552(2) 0.0309(7) Uani 1 1 d . . . . .
H20A H 0.705475 0.820907 -0.046221 0.037 Uiso 1 1 calc R U . . .
C20B C 0.8105(3) 0.4416(3) 0.2938(2) 0.0318(7) Uani 1 1 d . . . . .
H20B H 0.73869 0.451802 0.281208 0.038 Uiso 1 1 calc R U . . .
C21A C 0.8323(2) 0.9586(2) 0.0227(2) 0.0239(6) Uani 1 1 d . . . . .
C21B C 0.8486(2) 0.4086(2) 0.3833(2) 0.0249(6) Uani 1 1 d . . . . .
N1A N 0.57886(19) 0.7915(2) 0.46020(18) 0.0248(5) Uani 1 1 d . . . . .
N1B N 0.45996(19) 0.6840(2) 0.23317(18) 0.0251(5) Uani 1 1 d . . . . .
N2A N 0.69456(18) 0.85593(19) 0.33083(17) 0.0217(5) Uani 1 1 d . . . . .
N2B N 0.51995(18) 0.53667(19) 0.32363(17) 0.0213(5) Uani 1 1 d . . . . .
N3A N 0.7514(2) 0.88420(19) 0.25918(18) 0.0241(5) Uani 1 1 d . . . . .
N3B N 0.55636(19) 0.46078(19) 0.36880(19) 0.0250(5) Uani 1 1 d . . . . .
N4A N 0.8226(2) 0.82553(19) 0.12576(18) 0.0252(5) Uani 1 1 d . . . . .
H4A1 H 0.834346 0.771615 0.084524 0.03 Uiso 1 1 calc R U . . .
N4B N 0.6975(2) 0.4245(2) 0.4703(2) 0.0290(6) Uani 1 1 d . . . . .
N5A N 0.9715(2) 1.13236(19) 0.07751(19) 0.0260(5) Uani 1 1 d . . . . .
N5B N 0.9933(2) 0.3510(2) 0.47791(19) 0.0285(6) Uani 1 1 d . . . . .
H5B H 1.061316 0.345416 0.487473 0.034 Uiso 1 1 calc R U . . .
N6A N 0.5515(2) 0.9360(3) 0.6234(2) 0.0408(7) Uani 1 1 d . . . . .
N6B N 0.2645(2) 0.6303(2) 0.0861(2) 0.0384(7) Uani 1 1 d . . . . .
S1A S 0.71009(6) 0.66408(6) 0.18740(6) 0.02751(18) Uani 1 1 d . . . . .
S1B S 0.73843(6) 0.63043(6) 0.45672(5) 0.02580(18) Uani 1 1 d . . . . .
Zn1 Zn 0.62446(3) 0.69131(3) 0.33125(3) 0.02214(13) Uani 1 1 d . . . . .
C1 C 1.0449(3) 1.3704(3) -0.0209(3) 0.0387(8) Uani 1 1 d . . . . .
H1A H 0.972677 1.358682 -0.003319 0.058 Uiso 1 1 d R U . . .
H1Z H 1.035343 1.345096 -0.094464 0.058 Uiso 1 1 d R U . . .
H1C H 1.083137 1.447566 -0.000731 0.058 Uiso 1 1 d R U . . .
O1 O 1.10831(17) 1.31192(17) 0.03117(16) 0.0312(5) Uani 1 1 d . . . . .
H1 H 1.065949 1.259766 0.045175 0.047 Uiso 1 1 d R U . . .
C2 C 0.6054(6) 0.0679(6) 0.1313(6) 0.056(2) Uani 0.5 1 d D . P . .
H2C H 0.552771 0.070764 0.176217 0.067 Uiso 0.5 1 calc R U P . .
H2D H 0.629861 0.001499 0.134008 0.067 Uiso 0.5 1 calc R U P . .
C3 C 0.5426(6) 0.0577(6) 0.0193(6) 0.053(2) Uani 0.5 1 d D . P . .
H3A H 0.479581 -0.006437 -0.000223 0.079 Uiso 0.5 1 d R U P . .
H3B H 0.516696 0.12211 0.014651 0.079 Uiso 0.5 1 d R U P . .
H3C H 0.592725 0.050497 -0.026703 0.079 Uiso 0.5 1 d R U P . .
O2 O 0.7023(8) 0.1622(6) 0.1731(6) 0.103(3) Uani 0.5 1 d D . P . .
H2 H 0.684393 0.212181 0.20823 0.154 Uiso 0.5 1 d R U P . .
C4 C 0.5173(5) 0.3705(5) 0.0776(5) 0.0345(14) Uiso 0.5 1 d D . P . .
H4C H 0.569838 0.441397 0.111459 0.041 Uiso 0.5 1 calc R U P . .
H4D H 0.539195 0.340679 0.015004 0.041 Uiso 0.5 1 calc R U P . .
C5 C 0.5121(15) 0.2930(13) 0.1488(12) 0.133(6) Uiso 0.5 1 d D . P . .
H5Z H 0.584927 0.281197 0.168772 0.2 Uiso 0.5 1 calc R U P . .
H5C H 0.489242 0.323924 0.209555 0.2 Uiso 0.5 1 calc R U P . .
H5D H 0.458833 0.223975 0.113835 0.2 Uiso 0.5 1 calc R U P . .
O3 O 0.4068(4) 0.3799(5) 0.0551(4) 0.0528(13) Uiso 0.5 1 d D . P . .
H3 H 0.405678 0.440686 0.043074 0.079 Uiso 0.5 1 d R U P . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1A N1A 1.345(4) . ?
C1A C2A 1.398(4) . ?
C1A C6A 1.476(4) . ?
C1B N1B 1.335(4) . ?
C1B C2B 1.390(5) . ?
C2A N6A 1.340(4) . ?
C2B N6B 1.327(5) . ?
C4A N6A 1.332(5) . ?
C4A C5A 1.387(5) . ?
C4B N6B 1.337(4) . ?
C4B C5B 1.393(4) . ?
C5A N1A 1.329(4) . ?
C5B N1B 1.340(4) . ?
C5B C6B 1.480(4) . ?
C6A N2A 1.297(4) . ?
C6A C8A 1.491(4) . ?
C6B N2B 1.291(4) . ?
C6B C8B 1.497(4) . ?
C7A N3A 1.325(4) . ?
C7A N4A 1.364(4) . ?
C7A S1A 1.725(3) . ?
C7B N3B 1.319(4) . ?
C7B N4B 1.373(4) . ?
C7B S1B 1.737(3) . ?
C9A C21A 1.398(4) . ?
C9A C10A 1.401(4) . ?
C9A N4A 1.416(4) . ?
C9B N4B 1.299(4) . ?
C9B C21B 1.459(4) . ?
C9B C10B 1.465(4) . ?
C10A C11A 1.423(4) . ?
C10A C15A 1.434(4) . ?
C10B C15B 1.397(4) . ?
C10B C11B 1.405(4) . ?
C11A C12A 1.365(5) . ?
C11B C12B 1.378(4) . ?
C12A C13A 1.415(5) . ?
C12B C13B 1.393(5) . ?
C13A C14A 1.359(5) . ?
C13B C14B 1.371(5) . ?
C14A C15A 1.422(4) . ?
C14B C15B 1.414(4) . ?
C15A N5A 1.348(4) . ?
C15B N5B 1.367(4) . ?
C16A N5A 1.345(4) . ?
C16A C17A 1.428(4) . ?
C16A C21A 1.433(4) . ?
C16B N5B 1.370(4) . ?
C16B C17B 1.402(4) . ?
C16B C21B 1.412(4) . ?
C17A C18A 1.357(5) . ?
C17B C18B 1.366(5) . ?
C18A C19A 1.421(5) . ?
C18B C19B 1.393(5) . ?
C19A C20A 1.360(5) . ?
C19B C20B 1.373(5) . ?
C20A C21A 1.429(4) . ?
C20B C21B 1.413(4) . ?
N1A Zn1 2.249(3) . ?
N1B Zn1 2.266(2) . ?
N2A N3A 1.369(3) . ?
N2A Zn1 2.131(2) . ?
N2B N3B 1.380(3) . ?
N2B Zn1 2.124(2) . ?
S1A Zn1 2.4238(8) . ?
S1B Zn1 2.4191(8) . ?
C1 O1 1.421(4) . ?
C2 O2 1.480(8) . ?
C2 C3 1.571(8) . ?
C3 C3 1.583(14) 2_655 ?
C4 O3 1.432(7) . ?
C4 C5 1.519(9) . ?

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
N1A C1A C2A 119.9(3) . . ?
N1A C1A C6A 116.9(3) . . ?
C2A C1A C6A 123.1(3) . . ?
N1B C1B C2B 121.2(3) . . ?
N6A C2A C1A 122.3(3) . . ?
N6B C2B C1B 122.1(3) . . ?
N6A C4A C5A 122.2(3) . . ?
N6B C4B C5B 122.6(3) . . ?
N1A C5A C4A 121.2(3) . . ?
N1B C5B C4B 120.2(3) . . ?
N1B C5B C6B 117.1(2) . . ?
C4B C5B C6B 122.6(3) . . ?
N2A C6A C1A 114.5(3) . . ?
N2A C6A C8A 124.2(3) . . ?
C1A C6A C8A 121.3(3) . . ?
N2B C6B C5B 115.1(2) . . ?
N2B C6B C8B 123.7(3) . . ?
C5B C6B C8B 121.2(3) . . ?
N3A C7A N4A 115.1(2) . . ?
N3A C7A S1A 129.3(2) . . ?
N4A C7A S1A 115.6(2) . . ?
N3B C7B N4B 115.3(3) . . ?
N3B C7B S1B 127.0(2) . . ?
N4B C7B S1B 117.2(2) . . ?
C21A C9A C10A 119.9(3) . . ?
C21A C9A N4A 118.3(3) . . ?
C10A C9A N4A 121.7(3) . . ?
N4B C9B C21B 126.9(3) . . ?
N4B C9B C10B 117.1(3) . . ?
C21B C9B C10B 116.1(3) . . ?
C9A C10A C11A 123.9(3) . . ?
C9A C10A C15A 117.6(3) . . ?
C11A C10A C15A 118.4(3) . . ?
C15B C10B C11B 118.6(3) . . ?
C15B C10B C9B 120.1(3) . . ?
C11B C10B C9B 121.1(3) . . ?
C12A C11A C10A 121.0(3) . . ?
C12B C11B C10B 120.9(3) . . ?
C11A C12A C13A 120.5(3) . . ?
C11B C12B C13B 119.7(3) . . ?
C14A C13A C12A 120.2(3) . . ?
C14B C13B C12B 121.0(3) . . ?
C13A C14A C15A 121.3(3) . . ?
C13B C14B C15B 119.4(3) . . ?
N5A C15A C14A 118.1(3) . . ?
N5A C15A C10A 123.3(3) . . ?
C14A C15A C10A 118.6(3) . . ?
N5B C15B C10B 120.0(3) . . ?
N5B C15B C14B 119.7(3) . . ?
C10B C15B C14B 120.3(3) . . ?
N5A C16A C17A 118.5(3) . . ?
N5A C16A C21A 123.1(3) . . ?
C17A C16A C21A 118.4(3) . . ?
N5B C16B C17B 119.1(3) . . ?
N5B C16B C21B 120.3(3) . . ?
C17B C16B C21B 120.6(3) . . ?
C18A C17A C16A 120.8(3) . . ?
C18B C17B C16B 120.0(3) . . ?
C17A C18A C19A 120.7(3) . . ?
C17B C18B C19B 120.7(3) . . ?
C20A C19A C18A 120.6(3) . . ?
C20B C19B C18B 119.8(3) . . ?
C19A C20A C21A 120.4(3) . . ?
C19B C20B C21B 121.7(3) . . ?
C9A C21A C20A 122.9(3) . . ?
C9A C21A C16A 118.0(3) . . ?
C20A C21A C16A 119.1(3) . . ?
C16B C21B C20B 117.1(3) . . ?
C16B C21B C9B 119.2(3) . . ?
C20B C21B C9B 123.7(3) . . ?
C5A N1A C1A 118.0(3) . . ?
C5A N1A Zn1 128.0(2) . . ?
C1A N1A Zn1 113.66(18) . . ?
C1B N1B C5B 117.5(3) . . ?
C1B N1B Zn1 128.6(2) . . ?
C5B N1B Zn1 112.49(18) . . ?
C6A N2A N3A 117.1(2) . . ?
C6A N2A Zn1 121.12(19) . . ?
N3A N2A Zn1 121.78(17) . . ?
C6B N2B N3B 117.0(2) . . ?
C6B N2B Zn1 120.58(19) . . ?
N3B N2B Zn1 122.41(17) . . ?
C7A N3A N2A 113.5(2) . . ?
C7B N3B N2B 113.4(2) . . ?
C7A N4A C9A 125.4(2) . . ?
C9B N4B C7B 127.7(2) . . ?
C16A N5A C15A 118.1(2) . . ?
C15B N5B C16B 122.7(3) . . ?
C4A N6A C2A 116.3(3) . . ?
C2B N6B C4B 116.3(3) . . ?
C7A S1A Zn1 94.32(10) . . ?
C7B S1B Zn1 95.12(10) . . ?
N2B Zn1 N2A 166.84(9) . . ?
N2B Zn1 N1A 100.47(9) . . ?
N2A Zn1 N1A 73.53(9) . . ?
N2B Zn1 N1B 74.01(9) . . ?
N2A Zn1 N1B 93.83(9) . . ?
N1A Zn1 N1B 87.81(9) . . ?
N2B Zn1 S1B 79.74(6) . . ?
N2A Zn1 S1B 111.27(6) . . ?
N1A Zn1 S1B 88.13(6) . . ?
N1B Zn1 S1B 152.22(7) . . ?
N2B Zn1 S1A 104.39(7) . . ?
N2A Zn1 S1A 81.00(6) . . ?
N1A Zn1 S1A 154.53(7) . . ?
N1B Zn1 S1A 93.73(6) . . ?
S1B Zn1 S1A 101.56(3) . . ?
O2 C2 C3 116.1(6) . . ?
C2 C3 C3 108.7(8) . 2_655 ?
O3 C4 C5 103.2(8) . . ?


# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH and EtOH'
