# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2026

####################################################################### 
# 
# 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_mo_v4_24dam04_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2433551'
loop_
_audit_author_name
_audit_author_address
'Frikkie Malan'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2025-11-26 deposited with the CCDC.	2025-12-08 downloaded from the CCDC.
;
_audit_creation_date             2025-11-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C18 H13 Cl N3 O3 Re), H2 O'
_chemical_formula_sum            'C36 H28 Cl2 N6 O7 Re2'
_chemical_formula_weight         1099.94
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   7.4384(3)
_cell_length_b                   15.5722(6)
_cell_length_c                   29.4061(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3406.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9828
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.285
_cell_measurement_theta_min      2.961
_shelx_estimated_absorpt_T_max   0.528
_shelx_estimated_absorpt_T_min   0.322
_exptl_absorpt_coefficient_mu    7.320
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1121 before and 0.0651 after correction.
The Ratio of minimum to maximum transmission is 0.5993.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.145
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2104
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            45010
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.289
_diffrn_reflns_theta_min         2.616
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.939
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                8252
_reflns_number_total             8332
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.

The notable negative residual electron density are located in regions of weak diffuse solvent/background scattering, and do not correspond to chemically meaningful positions. These residual features are therefore attributed to termination effects and minor Fourier truncation associated with the weakly scattering lattice water.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'SAINT V8.40B (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.592
_refine_diff_density_min         -1.969
_refine_diff_density_rms         0.155
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.115(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     486
_refine_ls_number_reflns         8332
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0272
_refine_ls_restrained_S_all      1.210
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+16.9160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0613
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.885(11)
 0.115(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
3. Restrained distances
 O5-H5D
 0.87 with sigma of 0.02
 H5C-H5D
 1.55 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
Uanis(C8A) = Uanis(C7A)
Uanis(O5) = Uanis(O4)
5. Others
 Fixed Sof: O4(0.5) H4A(0.5) H4B(0.5) O5(0.5) H5C(0.5) H5D(0.5)
6.a Free rotating group:
 O4(H4A,H4B), O5(H5C,H5D)
6.b Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C5B(H5B), C16A(H16A), C15A(H15A), C14A(H14A), C13A(H13A),
 C10A(H10A), C8A(H8A), C16B(H16B), C15B(H15B), C14B(H14B), C13B(H13B),
 C10B(H10B), C8B(H8B)
6.c Idealised Me refined as rotating group:
 C6A1(H6AA,H6AB,H6AC), C7A1(H7AA,H7AB,H7AC), C6B1(H6BA,H6BB,H6BC), C7B1(H7BA,
 H7BB,H7BC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Re1A Re 0.20888(4) 0.82392(2) 0.39115(2) 0.01273(7) Uani 1 1 d . . . . .
Re1B Re 0.44894(4) 0.67067(2) 0.60901(2) 0.01203(7) Uani 1 1 d . . . . .
Cl1A Cl 0.4569(3) 0.81880(12) 0.33377(7) 0.0186(4) Uani 1 1 d . . . . .
Cl1B Cl 0.6849(3) 0.67217(12) 0.66962(7) 0.0183(4) Uani 1 1 d . . . . .
O1 O 0.2877(10) 1.0105(4) 0.4162(2) 0.0250(15) Uani 1 1 d . . . . .
O2 O 0.4558(9) 0.7834(4) 0.4719(2) 0.0247(14) Uani 1 1 d . . . . .
O3 O -0.1025(10) 0.8249(4) 0.4594(2) 0.0235(14) Uani 1 1 d . . . . .
O7 O 0.1659(9) 0.6805(4) 0.5335(2) 0.0194(12) Uani 1 1 d . . . . .
O8 O 0.5063(12) 0.4830(4) 0.5828(2) 0.0264(14) Uani 1 1 d . . . . .
O6 O 0.7416(8) 0.7047(4) 0.5385(2) 0.0215(13) Uani 1 1 d . . . . .
C5A C 0.2426(11) 0.6019(5) 0.4185(3) 0.0117(14) Uani 1 1 d . . . . .
H5A H 0.275128 0.649300 0.437088 0.014 Uiso 1 1 calc R U . . .
N1B N 0.2702(10) 0.6419(4) 0.6647(2) 0.0135(13) Uani 1 1 d . . . . .
C5B C 0.4948(12) 0.8919(5) 0.5797(3) 0.0146(15) Uani 1 1 d . . . . .
H5B H 0.528231 0.843772 0.561742 0.018 Uiso 1 1 calc R U . . .
N2B N 0.3760(10) 0.7974(4) 0.6386(2) 0.0119(12) Uani 1 1 d . . . . .
N1A N 0.0397(10) 0.8572(5) 0.3336(2) 0.0179(14) Uani 1 1 d . . . . .
C16A C -0.0080(11) 0.9375(5) 0.3229(3) 0.0168(15) Uani 1 1 d . . . . .
H16A H 0.031971 0.983202 0.341743 0.020 Uiso 1 1 calc R U . . .
C15A C -0.1129(12) 0.9569(5) 0.2855(3) 0.0200(16) Uani 1 1 d . . . . .
H15A H -0.146369 1.014508 0.279027 0.024 Uiso 1 1 calc R U . . .
C14A C -0.1677(12) 0.8902(5) 0.2577(3) 0.0214(17) Uani 1 1 d . . . . .
H14A H -0.238034 0.901576 0.231415 0.026 Uiso 1 1 calc R U . . .
C13A C -0.1193(13) 0.8065(5) 0.2686(3) 0.0213(17) Uani 1 1 d . . . . .
H13A H -0.158838 0.759552 0.250532 0.026 Uiso 1 1 calc R U . . .
C12A C -0.0116(10) 0.7935(5) 0.3065(3) 0.0140(15) Uani 1 1 d . . . . .
C11A C 0.0454(10) 0.7067(5) 0.3203(3) 0.0129(15) Uani 1 1 d . . . . .
C10A C 0.0094(11) 0.6332(5) 0.2928(3) 0.0158(15) Uani 1 1 d . . . . .
H10A H -0.047013 0.641595 0.264182 0.019 Uiso 1 1 calc R U . . .
N3A N 0.0498(9) 0.5549(4) 0.3050(2) 0.0137(13) Uani 1 1 d . . . . .
C9A C 0.1256(10) 0.5453(5) 0.3470(3) 0.0130(14) Uani 1 1 d . . . . .
C4A C 0.1681(10) 0.6166(5) 0.3750(3) 0.0105(14) Uani 1 1 d . . . . .
C6A C 0.2689(11) 0.5188(5) 0.4343(3) 0.0134(15) Uani 1 1 d . . . . .
C6A1 C 0.3424(12) 0.5047(5) 0.4808(3) 0.0159(16) Uani 1 1 d . . . . .
H6AA H 0.395351 0.558197 0.492088 0.024 Uiso 1 1 calc R U . . .
H6AB H 0.434943 0.459933 0.479693 0.024 Uiso 1 1 calc R U . . .
H6AC H 0.245277 0.486579 0.501161 0.024 Uiso 1 1 calc R U . . .
C7A C 0.2225(10) 0.4473(5) 0.4060(3) 0.0145(11) Uani 1 1 d . . . . .
C7A1 C 0.2429(13) 0.3583(5) 0.4237(3) 0.0185(16) Uani 1 1 d . . . . .
H7AA H 0.367846 0.348935 0.433066 0.028 Uiso 1 1 calc R U . . .
H7AB H 0.210870 0.317138 0.399877 0.028 Uiso 1 1 calc R U . . .
H7AC H 0.163367 0.350259 0.449974 0.028 Uiso 1 1 calc R U . . .
C8A C 0.1562(11) 0.4618(5) 0.3639(3) 0.0145(11) Uani 1 1 d . . . . .
H8A H 0.129442 0.414074 0.344926 0.017 Uiso 1 1 calc R U . . .
N2A N 0.1317(8) 0.6998(4) 0.3601(2) 0.0118(12) Uani 1 1 d . . . . .
C2A C 0.2594(12) 0.9407(5) 0.4073(3) 0.0176(15) Uani 1 1 d . . . . .
C1A C 0.3652(11) 0.7951(5) 0.4415(3) 0.0159(15) Uani 1 1 d . . . . .
C3A C 0.0101(14) 0.8245(5) 0.4336(3) 0.0157(16) Uani 1 1 d . . . . .
C3B C 0.2686(11) 0.6769(5) 0.5630(3) 0.0141(16) Uani 1 1 d . . . . .
C16B C 0.2139(11) 0.5619(5) 0.6757(3) 0.0166(15) Uani 1 1 d . . . . .
H16B H 0.245395 0.515431 0.656340 0.020 Uiso 1 1 calc R U . . .
C15B C 0.1127(12) 0.5456(6) 0.7138(3) 0.0211(17) Uani 1 1 d . . . . .
H15B H 0.078944 0.488371 0.721073 0.025 Uiso 1 1 calc R U . . .
C14B C 0.0602(12) 0.6126(6) 0.7415(3) 0.0216(17) Uani 1 1 d . . . . .
H14B H -0.014711 0.602519 0.767166 0.026 Uiso 1 1 calc R U . . .
C13B C 0.1188(11) 0.6951(5) 0.7313(3) 0.0168(15) Uani 1 1 d . . . . .
H13B H 0.088472 0.742319 0.750240 0.020 Uiso 1 1 calc R U . . .
C12B C 0.2247(11) 0.7067(5) 0.6920(3) 0.0154(15) Uani 1 1 d . . . . .
C11B C 0.2870(11) 0.7929(5) 0.6783(3) 0.0153(15) Uani 1 1 d . . . . .
C10B C 0.2529(11) 0.8668(5) 0.7043(3) 0.0167(15) Uani 1 1 d . . . . .
H10B H 0.193767 0.860056 0.732733 0.020 Uiso 1 1 calc R U . . .
N3B N 0.2983(10) 0.9444(4) 0.6916(3) 0.0179(15) Uani 1 1 d . . . . .
C9B C 0.3761(11) 0.9509(5) 0.6497(3) 0.0154(16) Uani 1 1 d . . . . .
C4B C 0.4184(11) 0.8782(5) 0.6232(3) 0.0125(14) Uani 1 1 d . . . . .
C6B C 0.5215(10) 0.9727(5) 0.5631(3) 0.0133(14) Uani 1 1 d . . . . .
C6B1 C 0.5948(12) 0.9850(5) 0.5152(3) 0.0165(16) Uani 1 1 d . . . . .
H6BA H 0.625001 0.929006 0.502096 0.025 Uiso 1 1 calc R U . . .
H6BB H 0.702918 1.020921 0.516382 0.025 Uiso 1 1 calc R U . . .
H6BC H 0.503622 1.013149 0.496299 0.025 Uiso 1 1 calc R U . . .
C7B C 0.4792(11) 1.0457(5) 0.5898(3) 0.0144(15) Uani 1 1 d . . . . .
C7B1 C 0.5007(13) 1.1345(5) 0.5707(3) 0.0207(17) Uani 1 1 d . . . . .
H7BA H 0.625246 1.142756 0.560831 0.031 Uiso 1 1 calc R U . . .
H7BB H 0.471040 1.176855 0.594209 0.031 Uiso 1 1 calc R U . . .
H7BC H 0.419734 1.141734 0.544738 0.031 Uiso 1 1 calc R U . . .
C8B C 0.4090(11) 1.0348(5) 0.6333(3) 0.0153(15) Uani 1 1 d . . . . .
H8B H 0.383429 1.083247 0.651766 0.018 Uiso 1 1 calc R U . . .
C2B C 0.4861(12) 0.5535(5) 0.5929(3) 0.0157(15) Uani 1 1 d . . . . .
C1B C 0.6315(11) 0.6958(5) 0.5642(3) 0.0147(15) Uani 1 1 d . . . . .
O4 O 0.435(2) 1.3311(9) 0.6059(11) 0.037(3) Uani 0.5 1 d G . P . .
H4A H 0.528825 1.312785 0.591224 0.055 Uiso 0.5 1 d G U P . .
H4B H 0.388662 1.370172 0.588290 0.055 Uiso 0.5 1 d G U P . .
O5 O 0.216(2) 0.1746(9) 0.3864(10) 0.037(3) Uani 0.5 1 d DG . P . .
H5C H 0.221689 0.119318 0.390352 0.055 Uiso 0.5 1 d DG U P . .
H5D H 0.302925 0.159939 0.352098 0.055 Uiso 0.5 1 d DG U P . .


_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
Re1A Cl1A 2.501(2) . ?
Re1A N1A 2.171(7) . ?
Re1A N2A 2.213(6) . ?
Re1A C2A 1.916(8) . ?
Re1A C1A 1.934(9) . ?
Re1A C3A 1.935(10) . ?
Re1B Cl1B 2.502(2) . ?
Re1B N1B 2.155(7) . ?
Re1B N2B 2.225(6) . ?
Re1B C3B 1.907(9) . ?
Re1B C2B 1.906(8) . ?
Re1B C1B 1.931(9) . ?
O1 C2A 1.139(10) . ?
O2 C1A 1.135(11) . ?
O3 C3A 1.130(12) . ?
O7 C3B 1.159(11) . ?
O8 C2B 1.146(10) . ?
O6 C1B 1.125(11) . ?
C5A H5A 0.9500 . ?
C5A C4A 1.413(10) . ?
C5A C6A 1.388(11) . ?
N1B C16B 1.353(10) . ?
N1B C12B 1.334(11) . ?
C5B H5B 0.9500 . ?
C5B C4B 1.416(12) . ?
C5B C6B 1.365(11) . ?
N2B C11B 1.343(11) . ?
N2B C4B 1.374(10) . ?
N1A C16A 1.339(10) . ?
N1A C12A 1.329(11) . ?
C16A H16A 0.9500 . ?
C16A C15A 1.381(12) . ?
C15A H15A 0.9500 . ?
C15A C14A 1.383(12) . ?
C14A H14A 0.9500 . ?
C14A C13A 1.389(11) . ?
C13A H13A 0.9500 . ?
C13A C12A 1.388(12) . ?
C12A C11A 1.474(10) . ?
C11A C10A 1.426(11) . ?
C11A N2A 1.340(10) . ?
C10A H10A 0.9500 . ?
C10A N3A 1.305(10) . ?
N3A C9A 1.367(10) . ?
C9A C4A 1.418(11) . ?
C9A C8A 1.409(10) . ?
C4A N2A 1.393(9) . ?
C6A C6A1 1.489(11) . ?
C6A C7A 1.433(11) . ?
C6A1 H6AA 0.9800 . ?
C6A1 H6AB 0.9800 . ?
C6A1 H6AC 0.9800 . ?
C7A C7A1 1.488(11) . ?
C7A C8A 1.353(13) . ?
C7A1 H7AA 0.9800 . ?
C7A1 H7AB 0.9800 . ?
C7A1 H7AC 0.9800 . ?
C8A H8A 0.9500 . ?
C16B H16B 0.9500 . ?
C16B C15B 1.375(12) . ?
C15B H15B 0.9500 . ?
C15B C14B 1.381(13) . ?
C14B H14B 0.9500 . ?
C14B C13B 1.390(11) . ?
C13B H13B 0.9500 . ?
C13B C12B 1.410(11) . ?
C12B C11B 1.475(11) . ?
C11B C10B 1.404(11) . ?
C10B H10B 0.9500 . ?
C10B N3B 1.310(11) . ?
N3B C9B 1.365(11) . ?
C9B C4B 1.409(10) . ?
C9B C8B 1.414(11) . ?
C6B C6B1 1.522(11) . ?
C6B C7B 1.418(11) . ?
C6B1 H6BA 0.9800 . ?
C6B1 H6BB 0.9800 . ?
C6B1 H6BC 0.9800 . ?
C7B C7B1 1.500(12) . ?
C7B C8B 1.390(11) . ?
C7B1 H7BA 0.9800 . ?
C7B1 H7BB 0.9800 . ?
C7B1 H7BC 0.9800 . ?
C8B H8B 0.9500 . ?
O4 H4A 0.8701 . ?
O4 H4B 0.8700 . ?
O5 H5C 0.8700 . ?
O5 H5D 1.2212 . ?

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 Re1A Cl1A 84.81(19) . . ?
N1A Re1A N2A 74.7(3) . . ?
N2A Re1A Cl1A 83.43(16) . . ?
C2A Re1A Cl1A 93.0(3) . . ?
C2A Re1A N1A 94.6(3) . . ?
C2A Re1A N2A 169.0(3) . . ?
C2A Re1A C1A 85.0(3) . . ?
C2A Re1A C3A 89.2(3) . . ?
C1A Re1A Cl1A 93.7(2) . . ?
C1A Re1A N1A 178.5(3) . . ?
C1A Re1A N2A 105.6(3) . . ?
C1A Re1A C3A 88.1(4) . . ?
C3A Re1A Cl1A 177.2(3) . . ?
C3A Re1A N1A 93.3(3) . . ?
C3A Re1A N2A 94.1(3) . . ?
N1B Re1B Cl1B 83.9(2) . . ?
N1B Re1B N2B 74.7(3) . . ?
N2B Re1B Cl1B 83.33(19) . . ?
C3B Re1B Cl1B 176.6(2) . . ?
C3B Re1B N1B 96.6(3) . . ?
C3B Re1B N2B 93.5(3) . . ?
C3B Re1B C1B 90.1(4) . . ?
C2B Re1B Cl1B 94.9(3) . . ?
C2B Re1B N1B 94.6(3) . . ?
C2B Re1B N2B 169.3(3) . . ?
C2B Re1B C3B 88.5(3) . . ?
C2B Re1B C1B 85.6(3) . . ?
C1B Re1B Cl1B 89.5(2) . . ?
C1B Re1B N1B 173.3(3) . . ?
C1B Re1B N2B 105.0(3) . . ?
C4A C5A H5A 119.7 . . ?
C6A C5A H5A 119.7 . . ?
C6A C5A C4A 120.6(7) . . ?
C16B N1B Re1B 124.3(5) . . ?
C12B N1B Re1B 117.2(5) . . ?
C12B N1B C16B 118.3(7) . . ?
C4B C5B H5B 119.3 . . ?
C6B C5B H5B 119.3 . . ?
C6B C5B C4B 121.4(8) . . ?
C11B N2B Re1B 114.4(5) . . ?
C11B N2B C4B 116.6(6) . . ?
C4B N2B Re1B 128.8(5) . . ?
C16A N1A Re1A 124.1(6) . . ?
C12A N1A Re1A 117.2(5) . . ?
C12A N1A C16A 118.6(7) . . ?
N1A C16A H16A 118.6 . . ?
N1A C16A C15A 122.8(7) . . ?
C15A C16A H16A 118.6 . . ?
C16A C15A H15A 120.9 . . ?
C16A C15A C14A 118.2(7) . . ?
C14A C15A H15A 120.9 . . ?
C15A C14A H14A 120.2 . . ?
C15A C14A C13A 119.5(8) . . ?
C13A C14A H14A 120.2 . . ?
C14A C13A H13A 120.9 . . ?
C12A C13A C14A 118.1(8) . . ?
C12A C13A H13A 120.9 . . ?
N1A C12A C13A 122.7(7) . . ?
N1A C12A C11A 115.9(7) . . ?
C13A C12A C11A 121.4(7) . . ?
C10A C11A C12A 121.8(7) . . ?
N2A C11A C12A 116.9(7) . . ?
N2A C11A C10A 121.4(7) . . ?
C11A C10A H10A 118.3 . . ?
N3A C10A C11A 123.4(8) . . ?
N3A C10A H10A 118.3 . . ?
C10A N3A C9A 116.4(7) . . ?
N3A C9A C4A 122.0(7) . . ?
N3A C9A C8A 119.0(8) . . ?
C8A C9A C4A 118.9(7) . . ?
C5A C4A C9A 119.0(7) . . ?
N2A C4A C5A 120.7(7) . . ?
N2A C4A C9A 120.2(7) . . ?
C5A C6A C6A1 119.8(7) . . ?
C5A C6A C7A 119.8(7) . . ?
C7A C6A C6A1 120.4(7) . . ?
C6A C6A1 H6AA 109.5 . . ?
C6A C6A1 H6AB 109.5 . . ?
C6A C6A1 H6AC 109.5 . . ?
H6AA C6A1 H6AB 109.5 . . ?
H6AA C6A1 H6AC 109.5 . . ?
H6AB C6A1 H6AC 109.5 . . ?
C6A C7A C7A1 119.8(8) . . ?
C8A C7A C6A 119.3(8) . . ?
C8A C7A C7A1 120.9(8) . . ?
C7A C7A1 H7AA 109.5 . . ?
C7A C7A1 H7AB 109.5 . . ?
C7A C7A1 H7AC 109.5 . . ?
H7AA C7A1 H7AB 109.5 . . ?
H7AA C7A1 H7AC 109.5 . . ?
H7AB C7A1 H7AC 109.5 . . ?
C9A C8A H8A 118.8 . . ?
C7A C8A C9A 122.4(8) . . ?
C7A C8A H8A 118.8 . . ?
C11A N2A Re1A 114.5(5) . . ?
C11A N2A C4A 116.2(6) . . ?
C4A N2A Re1A 129.2(5) . . ?
O1 C2A Re1A 178.9(8) . . ?
O2 C1A Re1A 175.7(7) . . ?
O3 C3A Re1A 177.9(8) . . ?
O7 C3B Re1B 176.5(8) . . ?
N1B C16B H16B 118.8 . . ?
N1B C16B C15B 122.3(8) . . ?
C15B C16B H16B 118.8 . . ?
C16B C15B H15B 120.1 . . ?
C16B C15B C14B 119.8(8) . . ?
C14B C15B H15B 120.1 . . ?
C15B C14B H14B 120.6 . . ?
C15B C14B C13B 118.8(8) . . ?
C13B C14B H14B 120.6 . . ?
C14B C13B H13B 120.9 . . ?
C14B C13B C12B 118.2(8) . . ?
C12B C13B H13B 120.9 . . ?
N1B C12B C13B 122.6(7) . . ?
N1B C12B C11B 116.3(7) . . ?
C13B C12B C11B 121.1(7) . . ?
N2B C11B C12B 116.1(7) . . ?
N2B C11B C10B 121.3(7) . . ?
C10B C11B C12B 122.6(8) . . ?
C11B C10B H10B 118.2 . . ?
N3B C10B C11B 123.6(8) . . ?
N3B C10B H10B 118.2 . . ?
C10B N3B C9B 115.9(7) . . ?
N3B C9B C4B 122.2(7) . . ?
N3B C9B C8B 116.8(7) . . ?
C4B C9B C8B 121.0(8) . . ?
N2B C4B C5B 121.9(7) . . ?
N2B C4B C9B 120.1(7) . . ?
C9B C4B C5B 117.9(7) . . ?
C5B C6B C6B1 120.0(7) . . ?
C5B C6B C7B 120.5(8) . . ?
C7B C6B C6B1 119.5(7) . . ?
C6B C6B1 H6BA 109.5 . . ?
C6B C6B1 H6BB 109.5 . . ?
C6B C6B1 H6BC 109.5 . . ?
H6BA C6B1 H6BB 109.5 . . ?
H6BA C6B1 H6BC 109.5 . . ?
H6BB C6B1 H6BC 109.5 . . ?
C6B C7B C7B1 120.5(8) . . ?
C8B C7B C6B 119.7(8) . . ?
C8B C7B C7B1 119.8(8) . . ?
C7B C7B1 H7BA 109.5 . . ?
C7B C7B1 H7BB 109.5 . . ?
C7B C7B1 H7BC 109.5 . . ?
H7BA C7B1 H7BB 109.5 . . ?
H7BA C7B1 H7BC 109.5 . . ?
H7BB C7B1 H7BC 109.5 . . ?
C9B C8B H8B 120.3 . . ?
C7B C8B C9B 119.5(8) . . ?
C7B C8B H8B 120.3 . . ?
O8 C2B Re1B 179.0(8) . . ?
O6 C1B Re1B 175.1(7) . . ?
H4A O4 H4B 104.5 . . ?
H5C O5 H5D 84.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4A O7 0.87 1.98 2.74(3) 145.2 4_575 yes
O4 H4B O8 0.87 1.97 2.518(17) 119.8 1_565 yes

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
Re1A N1A C16A C15A 178.6(6) . . . . ?
Re1A N1A C12A C13A -179.8(6) . . . . ?
Re1A N1A C12A C11A 3.1(9) . . . . ?
Re1B N1B C16B C15B 174.1(6) . . . . ?
Re1B N1B C12B C13B -175.6(6) . . . . ?
Re1B N1B C12B C11B 6.1(9) . . . . ?
Re1B N2B C11B C12B -10.0(9) . . . . ?
Re1B N2B C11B C10B 171.3(6) . . . . ?
Re1B N2B C4B C5B 10.9(11) . . . . ?
Re1B N2B C4B C9B -172.9(6) . . . . ?
C5A C4A N2A Re1A 9.9(10) . . . . ?
C5A C4A N2A C11A -173.8(7) . . . . ?
C5A C6A C7A C7A1 -177.3(8) . . . . ?
C5A C6A C7A C8A 1.1(11) . . . . ?
N1B C16B C15B C14B 2.2(13) . . . . ?
N1B C12B C11B N2B 2.9(11) . . . . ?
N1B C12B C11B C10B -178.4(8) . . . . ?
C5B C6B C7B C7B1 -177.2(8) . . . . ?
C5B C6B C7B C8B -0.4(11) . . . . ?
N2B C11B C10B N3B 2.5(13) . . . . ?
N1A C16A C15A C14A -1.2(13) . . . . ?
N1A C12A C11A C10A -176.0(7) . . . . ?
N1A C12A C11A N2A 4.5(10) . . . . ?
C16A N1A C12A C13A -3.0(12) . . . . ?
C16A N1A C12A C11A -180.0(7) . . . . ?
C16A C15A C14A C13A 1.2(13) . . . . ?
C15A C14A C13A C12A -2.1(13) . . . . ?
C14A C13A C12A N1A 3.0(13) . . . . ?
C14A C13A C12A C11A 179.9(8) . . . . ?
C13A C12A C11A C10A 6.9(12) . . . . ?
C13A C12A C11A N2A -172.6(7) . . . . ?
C12A N1A C16A C15A 2.0(12) . . . . ?
C12A C11A C10A N3A -176.5(8) . . . . ?
C12A C11A N2A Re1A -9.6(8) . . . . ?
C12A C11A N2A C4A 173.6(7) . . . . ?
C11A C10A N3A C9A 2.0(12) . . . . ?
C10A C11A N2A Re1A 170.9(6) . . . . ?
C10A C11A N2A C4A -5.9(10) . . . . ?
C10A N3A C9A C4A -3.6(11) . . . . ?
C10A N3A C9A C8A 173.9(7) . . . . ?
N3A C9A C4A C5A 178.6(7) . . . . ?
N3A C9A C4A N2A 0.5(11) . . . . ?
N3A C9A C8A C7A -176.7(7) . . . . ?
C9A C4A N2A Re1A -172.0(5) . . . . ?
C9A C4A N2A C11A 4.3(10) . . . . ?
C4A C5A C6A C6A1 -178.1(7) . . . . ?
C4A C5A C6A C7A 0.9(12) . . . . ?
C4A C9A C8A C7A 0.9(11) . . . . ?
C6A C5A C4A C9A -2.0(11) . . . . ?
C6A C5A C4A N2A 176.1(8) . . . . ?
C6A C7A C8A C9A -2.0(11) . . . . ?
C6A1 C6A C7A C7A1 1.8(12) . . . . ?
C6A1 C6A C7A C8A -179.9(7) . . . . ?
C7A1 C7A C8A C9A 176.3(8) . . . . ?
C8A C9A C4A C5A 1.1(11) . . . . ?
C8A C9A C4A N2A -177.0(7) . . . . ?
N2A C11A C10A N3A 3.0(12) . . . . ?
C16B N1B C12B C13B -0.9(12) . . . . ?
C16B N1B C12B C11B -179.2(7) . . . . ?
C16B C15B C14B C13B -3.1(13) . . . . ?
C15B C14B C13B C12B 2.1(13) . . . . ?
C14B C13B C12B N1B -0.1(13) . . . . ?
C14B C13B C12B C11B 178.1(8) . . . . ?
C13B C12B C11B N2B -175.4(8) . . . . ?
C13B C12B C11B C10B 3.2(13) . . . . ?
C12B N1B C16B C15B -0.2(12) . . . . ?
C12B C11B C10B N3B -176.1(8) . . . . ?
C11B N2B C4B C5B -173.2(7) . . . . ?
C11B N2B C4B C9B 2.9(11) . . . . ?
C11B C10B N3B C9B 2.6(12) . . . . ?
C10B N3B C9B C4B -4.9(12) . . . . ?
C10B N3B C9B C8B 173.7(8) . . . . ?
N3B C9B C4B C5B 178.5(7) . . . . ?
N3B C9B C4B N2B 2.2(12) . . . . ?
N3B C9B C8B C7B -176.6(7) . . . . ?
C4B C5B C6B C6B1 -176.8(7) . . . . ?
C4B C5B C6B C7B 2.4(12) . . . . ?
C4B N2B C11B C12B 173.5(7) . . . . ?
C4B N2B C11B C10B -5.2(12) . . . . ?
C4B C9B C8B C7B 1.9(12) . . . . ?
C6B C5B C4B N2B 174.0(8) . . . . ?
C6B C5B C4B C9B -2.2(12) . . . . ?
C6B C7B C8B C9B -1.7(10) . . . . ?
C6B1 C6B C7B C7B1 2.0(11) . . . . ?
C6B1 C6B C7B C8B 178.8(7) . . . . ?
C7B1 C7B C8B C9B 175.1(8) . . . . ?
C8B C9B C4B C5B 0.0(12) . . . . ?
C8B C9B C4B N2B -176.3(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.885(11)
2 0.115(11)

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

data_am108_lt_auto
_database_code_depnum_ccdc_archive 'CCDC 2433822'
loop_
_audit_author_name
_audit_author_address
'Federrick P Malan'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2025-10-11 deposited with the CCDC.	2025-12-08 downloaded from the CCDC.
;
_audit_creation_date             2025-03-25
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 N3'
_chemical_formula_sum            'C15 H13 N3'
_chemical_formula_weight         235.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H12 N2 O'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.9662(4)
_cell_length_b                   7.4448(3)
_cell_length_c                   26.0051(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2316.69(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12440
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      31.1200
_cell_measurement_theta_min      3.2750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51523
_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_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.175
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.834
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            22431
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.155
_diffrn_reflns_theta_min         3.133
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.834
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00   8.00   0.50    2.00    --   -6.23 -48.00 -66.00  174
  2  ω    -18.00  27.00   0.50    2.00    --   -6.23 -99.00 -60.00   90
  3  ω    -37.00  31.00   0.50    2.00    --    4.59 -85.00  84.00  136
  4  ω    -18.00  27.00   0.50    2.00    --   -6.23 -99.00 150.00   90
  5  ω    -19.00  28.00   0.50    2.00    --   -6.23  37.00 -90.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0423849000
_diffrn_orient_matrix_UB_12      -0.0557849000
_diffrn_orient_matrix_UB_13      -0.0104082000
_diffrn_orient_matrix_UB_21      -0.0307750000
_diffrn_orient_matrix_UB_22      -0.0075923000
_diffrn_orient_matrix_UB_23      -0.0232108000
_diffrn_orient_matrix_UB_31      0.0277417000
_diffrn_orient_matrix_UB_32      0.0768536000
_diffrn_orient_matrix_UB_33      -0.0098490000
_diffrn_oxdiff_digest_hkl        
;
01bdab8654b1cc1e6ef9e3deef26b717792387
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2578
_reflns_number_total             3121
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0653P)²+0.6124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1222
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C3(H3), C10(H10), C11(H11), C13(H13), C12(H12)
1.b Idealised Me refined as rotating group:
 C7A1(H7AA,H7AB,H7AC), C6A1(H6AA,H6AB,H6AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N2 N 0.72622(7) 0.38971(12) 0.36694(3) 0.01913(19) Uani 1 1 d . . . . .
N3 N 0.50690(7) 0.53569(12) 0.36539(3) 0.0210(2) Uani 1 1 d . . . . .
N1 N 0.65542(8) 0.35049(13) 0.49898(3) 0.0244(2) Uani 1 1 d . . . . .
C5 C 0.51219(8) 0.53317(13) 0.27276(4) 0.0192(2) Uani 1 1 d . . . . .
H5 H 0.439658 0.585000 0.271981 0.023 Uiso 1 1 calc R U . . .
C9 C 0.67320(8) 0.42643(13) 0.32164(4) 0.0175(2) Uani 1 1 d . . . . .
C4 C 0.56388(8) 0.50020(13) 0.32066(4) 0.0178(2) Uani 1 1 d . . . . .
C2 C 0.66979(8) 0.42345(13) 0.40943(4) 0.0187(2) Uani 1 1 d . . . . .
C1 C 0.72413(8) 0.38177(13) 0.45926(4) 0.0191(2) Uani 1 1 d . . . . .
C7 C 0.67449(8) 0.41493(13) 0.22831(4) 0.0183(2) Uani 1 1 d . . . . .
C6 C 0.56458(8) 0.49188(13) 0.22729(4) 0.0188(2) Uani 1 1 d . . . . .
C8 C 0.72644(8) 0.38470(14) 0.27459(4) 0.0188(2) Uani 1 1 d . . . . .
H8 H 0.799502 0.334816 0.275013 0.023 Uiso 1 1 calc R U . . .
C3 C 0.55927(8) 0.49595(14) 0.40830(4) 0.0206(2) Uani 1 1 d . . . . .
H3 H 0.521967 0.516344 0.440016 0.025 Uiso 1 1 calc R U . . .
C10 C 0.84013(9) 0.37248(15) 0.46327(4) 0.0236(2) Uani 1 1 d . . . . .
H10 H 0.886257 0.398796 0.434503 0.028 Uiso 1 1 calc R U . . .
C7A1 C 0.73035(9) 0.36106(15) 0.17883(4) 0.0231(2) Uani 1 1 d . . . . .
H7AA H 0.686108 0.267337 0.161930 0.035 Uiso 1 1 calc R U . . .
H7AB H 0.805381 0.314981 0.186197 0.035 Uiso 1 1 calc R U . . .
H7AC H 0.735966 0.465774 0.156143 0.035 Uiso 1 1 calc R U . . .
C11 C 0.88685(9) 0.32417(15) 0.50996(4) 0.0269(2) Uani 1 1 d . . . . .
H11 H 0.965645 0.316535 0.513844 0.032 Uiso 1 1 calc R U . . .
C6A1 C 0.50593(9) 0.52144(15) 0.17672(4) 0.0237(2) Uani 1 1 d . . . . .
H6AA H 0.497642 0.406325 0.158844 0.036 Uiso 1 1 calc R U . . .
H6AB H 0.550046 0.603736 0.155434 0.036 Uiso 1 1 calc R U . . .
H6AC H 0.431952 0.573498 0.182987 0.036 Uiso 1 1 calc R U . . .
C13 C 0.70230(9) 0.30388(16) 0.54372(4) 0.0272(3) Uani 1 1 d . . . . .
H13 H 0.654572 0.280929 0.572159 0.033 Uiso 1 1 calc R U . . .
C12 C 0.81651(10) 0.28718(15) 0.55092(4) 0.0267(2) Uani 1 1 d . . . . .
H12 H 0.845960 0.251145 0.583242 0.032 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
N2 C9 1.3658(12) . ?
N2 C2 1.3190(12) . ?
N3 C4 1.3738(12) . ?
N3 C3 1.3136(13) . ?
N1 C1 1.3406(13) . ?
N1 C13 1.3374(13) . ?
C5 H5 0.9500 . ?
C5 C4 1.4123(13) . ?
C5 C6 1.3734(13) . ?
C9 C4 1.4190(14) . ?
C9 C8 1.4139(13) . ?
C2 C1 1.4827(13) . ?
C2 C3 1.4288(14) . ?
C1 C10 1.3937(14) . ?
C7 C6 1.4347(14) . ?
C7 C8 1.3733(13) . ?
C7 C7A1 1.5043(13) . ?
C6 C6A1 1.5068(13) . ?
C8 H8 0.9500 . ?
C3 H3 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.3844(14) . ?
C7A1 H7AA 0.9800 . ?
C7A1 H7AB 0.9800 . ?
C7A1 H7AC 0.9800 . ?
C11 H11 0.9500 . ?
C11 C12 1.3852(15) . ?
C6A1 H6AA 0.9800 . ?
C6A1 H6AB 0.9800 . ?
C6A1 H6AC 0.9800 . ?
C13 H13 0.9500 . ?
C13 C12 1.3850(15) . ?
C12 H12 0.9500 . ?

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 N2 C9 116.53(8) . . ?
C3 N3 C4 116.05(9) . . ?
C13 N1 C1 117.26(9) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C6 C5 C4 121.37(9) . . ?
N2 C9 C4 121.41(8) . . ?
N2 C9 C8 119.54(9) . . ?
C8 C9 C4 119.01(8) . . ?
N3 C4 C5 119.73(9) . . ?
N3 C4 C9 121.12(8) . . ?
C5 C4 C9 119.13(8) . . ?
N2 C2 C1 117.89(8) . . ?
N2 C2 C3 121.91(9) . . ?
C3 C2 C1 120.20(8) . . ?
N1 C1 C2 116.15(8) . . ?
N1 C1 C10 123.01(9) . . ?
C10 C1 C2 120.83(9) . . ?
C6 C7 C7A1 119.87(8) . . ?
C8 C7 C6 119.77(8) . . ?
C8 C7 C7A1 120.32(9) . . ?
C5 C6 C7 119.47(9) . . ?
C5 C6 C6A1 120.41(9) . . ?
C7 C6 C6A1 120.10(9) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 C9 121.23(9) . . ?
C7 C8 H8 119.4 . . ?
N3 C3 C2 122.96(9) . . ?
N3 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
C1 C10 H10 120.6 . . ?
C11 C10 C1 118.72(9) . . ?
C11 C10 H10 120.6 . . ?
C7 C7A1 H7AA 109.5 . . ?
C7 C7A1 H7AB 109.5 . . ?
C7 C7A1 H7AC 109.5 . . ?
H7AA C7A1 H7AB 109.5 . . ?
H7AA C7A1 H7AC 109.5 . . ?
H7AB C7A1 H7AC 109.5 . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.74(10) . . ?
C12 C11 H11 120.6 . . ?
C6 C6A1 H6AA 109.5 . . ?
C6 C6A1 H6AB 109.5 . . ?
C6 C6A1 H6AC 109.5 . . ?
H6AA C6A1 H6AB 109.5 . . ?
H6AA C6A1 H6AC 109.5 . . ?
H6AB C6A1 H6AC 109.5 . . ?
N1 C13 H13 118.1 . . ?
N1 C13 C12 123.71(10) . . ?
C12 C13 H13 118.1 . . ?
C11 C12 H12 120.7 . . ?
C13 C12 C11 118.53(10) . . ?
C13 C12 H12 120.7 . . ?

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
N2 C9 C4 N3 -0.68(15) . . . . ?
N2 C9 C4 C5 -179.08(9) . . . . ?
N2 C9 C8 C7 178.14(9) . . . . ?
N2 C2 C1 N1 -155.19(9) . . . . ?
N2 C2 C1 C10 23.42(14) . . . . ?
N2 C2 C3 N3 -0.77(16) . . . . ?
N1 C1 C10 C11 1.76(16) . . . . ?
N1 C13 C12 C11 1.38(18) . . . . ?
C9 N2 C2 C1 178.83(8) . . . . ?
C9 N2 C2 C3 -0.48(14) . . . . ?
C4 N3 C3 C2 1.24(15) . . . . ?
C4 C5 C6 C7 -0.50(15) . . . . ?
C4 C5 C6 C6A1 177.55(9) . . . . ?
C4 C9 C8 C7 0.26(15) . . . . ?
C2 N2 C9 C4 1.15(14) . . . . ?
C2 N2 C9 C8 -176.68(9) . . . . ?
C2 C1 C10 C11 -176.75(10) . . . . ?
C1 N1 C13 C12 0.21(17) . . . . ?
C1 C2 C3 N3 179.93(9) . . . . ?
C1 C10 C11 C12 -0.09(16) . . . . ?
C6 C5 C4 N3 -177.05(9) . . . . ?
C6 C5 C4 C9 1.37(15) . . . . ?
C6 C7 C8 C9 0.62(15) . . . . ?
C8 C9 C4 N3 177.16(9) . . . . ?
C8 C9 C4 C5 -1.24(14) . . . . ?
C8 C7 C6 C5 -0.51(15) . . . . ?
C8 C7 C6 C6A1 -178.56(9) . . . . ?
C3 N3 C4 C5 177.85(9) . . . . ?
C3 N3 C4 C9 -0.54(14) . . . . ?
C3 C2 C1 N1 24.14(14) . . . . ?
C3 C2 C1 C10 -157.25(10) . . . . ?
C10 C11 C12 C13 -1.37(17) . . . . ?
C7A1 C7 C6 C5 177.08(9) . . . . ?
C7A1 C7 C6 C6A1 -0.98(14) . . . . ?
C7A1 C7 C8 C9 -176.96(9) . . . . ?
C13 N1 C1 C2 176.77(10) . . . . ?
C13 N1 C1 C10 -1.80(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.897
_oxdiff_exptl_absorpt_empirical_full_min 0.624
