# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_cps4615-1-08_0001_run0_hkl4_sg60
_database_code_depnum_ccdc_archive 'CCDC 2484683'
loop_
_audit_author_name
_audit_author_address
'Hamilton Napolitano'
;State University of Goias
Brazil
;
_audit_update_record             
;
2025-09-02 deposited with the CCDC.	2025-11-27 downloaded from the CCDC.
;
_audit_creation_date             2025-01-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            Azines
_chemical_name_systematic        
(1E,2E)-bis[1-(4-nitrophenyl)-ethylidene]-hydrazine
_chemical_formula_moiety         'C16 H14 N4 O4'
_chemical_formula_sum            'C16 H14 N4 O4'
_chemical_formula_weight         326.31
_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 0.0026 0.0014 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0056 0.0028 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0054 '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'

_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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   12.680(5)
_cell_length_b                   11.488(8)
_cell_length_c                   20.223(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2946(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    48866
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      60
_cell_measurement_theta_min      2
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.803
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            48828
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.803
_diffrn_reflns_theta_full        23.710
_diffrn_reflns_theta_max         30.032
_diffrn_reflns_theta_min         1.899
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.803
_diffrn_measurement_device_type  'Pilatus 2M detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.67019
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3926
_reflns_number_total             4136
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    ?
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       0.025(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         4136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.064
_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)+(0.0786P)²+0.4931P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1259
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C12(H12), C3(H3), C2(H2), C13(H13), C15(H15)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.13976(6) 0.70857(6) 0.09119(3) 0.02359(17) Uani 1 1 d . . . . .
O1 O 0.13598(6) 0.16153(6) -0.08223(4) 0.03425(18) Uani 1 1 d . . . . .
N1 N 0.13785(6) 0.26505(7) -0.09792(4) 0.02503(17) Uani 1 1 d . . . . .
O2 O 0.14385(6) 0.29966(6) -0.15537(3) 0.03137(17) Uani 1 1 d . . . . .
C7 C 0.11631(7) 0.60356(7) 0.10898(4) 0.02098(17) Uani 1 1 d . . . . .
N3 N 0.14266(6) 0.78926(6) 0.14263(3) 0.02377(17) Uani 1 1 d . . . . .
O3 O 0.12390(7) 1.33719(6) 0.31659(4) 0.0407(2) Uani 1 1 d . . . . .
C1 C 0.13267(7) 0.35203(7) -0.04486(4) 0.02247(17) Uani 1 1 d . . . . .
C14 C 0.13455(7) 1.14698(7) 0.27884(4) 0.02336(18) Uani 1 1 d . . . . .
N4 N 0.12675(7) 1.23364(7) 0.33195(4) 0.02797(18) Uani 1 1 d . . . . .
C11 C 0.13392(6) 0.98371(7) 0.17832(4) 0.01961(16) Uani 1 1 d . . . . .
O4 O 0.12184(6) 1.19878(7) 0.38949(3) 0.03560(18) Uani 1 1 d . . . . .
C4 C 0.12098(6) 0.51544(7) 0.05513(4) 0.02014(16) Uani 1 1 d . . . . .
C16 C 0.13635(7) 1.10272(7) 0.16379(4) 0.02249(17) Uani 1 1 d . . . . .
C9 C 0.12714(6) 0.89576(7) 0.12456(4) 0.02032(17) Uani 1 1 d . . . . .
C6 C 0.15597(7) 0.46715(7) -0.05957(4) 0.02376(18) Uani 1 1 d . . . . .
H6 H 0.175004 0.489179 -0.102185 0.029 Uiso 1 1 calc R U . . .
C5 C 0.15014(7) 0.54831(7) -0.00914(4) 0.02322(17) Uani 1 1 d . . . . .
H5 H 0.165792 0.625856 -0.017985 0.028 Uiso 1 1 calc R U . . .
C8 C 0.08604(7) 0.56632(7) 0.17759(4) 0.02560(18) Uani 1 1 d . . . . .
H8A H 0.090064 0.631907 0.206903 0.038 Uiso 1 1 calc R U . . .
H8B H 0.133425 0.506659 0.192488 0.038 Uiso 1 1 calc R U . . .
H8C H 0.015282 0.536606 0.177242 0.038 Uiso 1 1 calc R U . . .
C12 C 0.13571(7) 0.94854(7) 0.24477(4) 0.02266(18) Uani 1 1 d . . . . .
H12 H 0.137299 0.869625 0.254983 0.027 Uiso 1 1 calc R U . . .
C3 C 0.09619(7) 0.39866(7) 0.06752(4) 0.02489(18) Uani 1 1 d . . . . .
H3 H 0.075324 0.376142 0.109713 0.030 Uiso 1 1 calc R U . . .
C2 C 0.10241(8) 0.31619(7) 0.01755(4) 0.02633(19) Uani 1 1 d . . . . .
H2 H 0.086566 0.238519 0.025875 0.032 Uiso 1 1 calc R U . . .
C10 C 0.09979(7) 0.93508(7) 0.05580(4) 0.02562(18) Uani 1 1 d . . . . .
H10A H 0.098450 0.869044 0.026724 0.038 Uiso 1 1 calc R U . . .
H10B H 0.151752 0.989705 0.040657 0.038 Uiso 1 1 calc R U . . .
H10C H 0.031708 0.971622 0.056093 0.038 Uiso 1 1 calc R U . . .
C13 C 0.13513(7) 1.02999(7) 0.29539(4) 0.02408(18) Uani 1 1 d . . . . .
H13 H 0.135134 1.006596 0.339421 0.029 Uiso 1 1 calc R U . . .
C15 C 0.13764(7) 1.18517(7) 0.21402(4) 0.02474(18) Uani 1 1 d . . . . .
H15 H 0.140529 1.264220 0.204280 0.030 Uiso 1 1 calc R U . . .
H16 H 0.1400(11) 1.1278(12) 0.1186(6) 0.041(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C7 1.2935(13) . ?
N2 N3 1.3939(12) . ?
O1 N1 1.2311(13) . ?
N1 O2 1.2304(12) . ?
N1 C1 1.4676(12) . ?
C7 C4 1.4881(12) . ?
C7 C8 1.5018(13) . ?
N3 C9 1.2920(13) . ?
O3 N4 1.2300(13) . ?
C1 C6 1.3873(14) . ?
C1 C2 1.3821(13) . ?
C14 N4 1.4677(12) . ?
C14 C13 1.3851(14) . ?
C14 C15 1.3829(13) . ?
N4 O4 1.2322(12) . ?
C11 C16 1.3987(14) . ?
C11 C9 1.4867(12) . ?
C11 C12 1.4034(12) . ?
C4 C5 1.4031(12) . ?
C4 C3 1.4005(14) . ?
C16 C15 1.3889(12) . ?
C16 H16 0.960(13) . ?
C9 C10 1.5026(12) . ?
C6 H6 0.9300 . ?
C6 C5 1.3839(12) . ?
C5 H5 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C12 H12 0.9300 . ?
C12 C13 1.3870(12) . ?
C3 H3 0.9300 . ?
C3 C2 1.3874(12) . ?
C2 H2 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C13 H13 0.9300 . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N2 N3 114.75(8) . . ?
O1 N1 C1 117.93(8) . . ?
O2 N1 O1 123.83(8) . . ?
O2 N1 C1 118.24(8) . . ?
N2 C7 C4 114.95(8) . . ?
N2 C7 C8 125.55(7) . . ?
C4 C7 C8 119.51(8) . . ?
C9 N3 N2 114.50(8) . . ?
C6 C1 N1 118.87(8) . . ?
C2 C1 N1 118.51(8) . . ?
C2 C1 C6 122.61(7) . . ?
C13 C14 N4 118.79(8) . . ?
C15 C14 N4 118.71(8) . . ?
C15 C14 C13 122.46(8) . . ?
O3 N4 C14 118.25(8) . . ?
O3 N4 O4 123.45(8) . . ?
O4 N4 C14 118.29(9) . . ?
C16 C11 C9 120.79(8) . . ?
C16 C11 C12 118.83(7) . . ?
C12 C11 C9 120.36(8) . . ?
C5 C4 C7 120.35(8) . . ?
C3 C4 C7 120.78(7) . . ?
C3 C4 C5 118.87(7) . . ?
C11 C16 H16 119.6(8) . . ?
C15 C16 C11 120.88(8) . . ?
C15 C16 H16 119.4(8) . . ?
N3 C9 C11 115.33(8) . . ?
N3 C9 C10 125.57(7) . . ?
C11 C9 C10 119.06(8) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 C1 118.22(8) . . ?
C5 C6 H6 120.9 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.02(8) . . ?
C6 C5 H5 119.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.83(8) . . ?
C13 C12 H12 119.6 . . ?
C4 C3 H3 119.6 . . ?
C2 C3 C4 120.73(8) . . ?
C2 C3 H3 119.6 . . ?
C1 C2 C3 118.53(8) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C14 C13 C12 118.44(8) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C14 C15 C16 118.46(8) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?

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 C7 C4 C5 0.60(11) . . . . ?
N2 C7 C4 C3 -179.23(8) . . . . ?
N2 N3 C9 C11 -177.80(7) . . . . ?
N2 N3 C9 C10 4.48(12) . . . . ?
O1 N1 C1 C6 167.06(8) . . . . ?
O1 N1 C1 C2 -14.36(12) . . . . ?
N1 C1 C6 C5 179.61(7) . . . . ?
N1 C1 C2 C3 -179.18(8) . . . . ?
O2 N1 C1 C6 -12.91(11) . . . . ?
O2 N1 C1 C2 165.67(8) . . . . ?
C7 N2 N3 C9 -155.71(9) . . . . ?
C7 C4 C5 C6 179.28(8) . . . . ?
C7 C4 C3 C2 -178.83(8) . . . . ?
N3 N2 C7 C4 -175.62(7) . . . . ?
N3 N2 C7 C8 4.32(12) . . . . ?
C1 C6 C5 C4 -0.30(12) . . . . ?
N4 C14 C13 C12 175.94(8) . . . . ?
N4 C14 C15 C16 -174.83(8) . . . . ?
C11 C16 C15 C14 -1.16(12) . . . . ?
C11 C12 C13 C14 -1.07(12) . . . . ?
C4 C3 C2 C1 -0.59(13) . . . . ?
C16 C11 C9 N3 169.20(8) . . . . ?
C16 C11 C9 C10 -12.93(11) . . . . ?
C16 C11 C12 C13 2.85(12) . . . . ?
C9 C11 C16 C15 176.93(7) . . . . ?
C9 C11 C12 C13 -175.80(8) . . . . ?
C6 C1 C2 C3 -0.66(14) . . . . ?
C5 C4 C3 C2 1.34(13) . . . . ?
C8 C7 C4 C5 -179.34(8) . . . . ?
C8 C7 C4 C3 0.82(12) . . . . ?
C12 C11 C16 C15 -1.71(12) . . . . ?
C12 C11 C9 N3 -12.18(11) . . . . ?
C12 C11 C9 C10 165.70(8) . . . . ?
C3 C4 C5 C6 -0.89(12) . . . . ?
C2 C1 C6 C5 1.10(13) . . . . ?
C13 C14 N4 O3 -178.38(9) . . . . ?
C13 C14 N4 O4 0.56(12) . . . . ?
C13 C14 C15 C16 3.05(13) . . . . ?
C15 C14 N4 O3 -0.42(13) . . . . ?
C15 C14 N4 O4 178.52(8) . . . . ?
C15 C14 C13 C12 -1.94(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cps4614-1-14_merge_a
_database_code_depnum_ccdc_archive 'CCDC 2484685'
loop_
_audit_author_name
_audit_author_address
'Hamilton Napolitano'
;State University of Goias
Brazil
;
_audit_update_record             
;
2025-09-02 deposited with the CCDC.	2025-11-27 downloaded from the CCDC.
;
_audit_creation_date             2025-01-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            Azines
_chemical_name_systematic        
(1E,2E)-1-benzylidene-2-[1-(4-nitrophenyl)-ethylidene]-hydrazine
_chemical_formula_moiety         'C15 H13 N3 O2'
_chemical_formula_sum            'C15 H13 N3 O2'
_chemical_formula_weight         267.28
_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 0.0026 0.0014 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0052 0.0029 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0054 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3240(17)
_cell_length_b                   9.3840(11)
_cell_length_c                   9.5750(10)
_cell_angle_alpha                105.669(5)
_cell_angle_beta                 105.283(8)
_cell_angle_gamma                116.786(4)
_cell_volume                     643.68(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    32769
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      60
_cell_measurement_theta_min      2
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.841
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            32769
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        23.710
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         2.330
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.841
_diffrn_measurement_device_type  'Pilatus 2M detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.67019
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3707
_reflns_number_total             3767
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.395
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.156
_refine_ls_extinction_coef       0.76(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3767
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0501
_refine_ls_restrained_S_all      1.099
_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)+(0.0807P)²+0.1209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1290
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C2(H2), C15(H15), C12(H12), C11(H11), C14(H14), C13(H13)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
N3 N 0.22303(10) 0.76914(10) 0.31321(9) 0.02140(17) Uani 1 1 d . . . . .
O1 O 1.16580(9) 1.12616(10) 0.16764(9) 0.02776(18) Uani 1 1 d . . . . .
N2 N 0.35374(9) 0.84256(10) 0.26106(9) 0.01977(17) Uani 1 1 d . . . . .
N1 N 1.06927(9) 1.18240(10) 0.16841(8) 0.02045(17) Uani 1 1 d . . . . .
C3 C 0.77784(11) 0.89980(10) 0.31321(10) 0.01787(17) Uani 1 1 d . . . . .
H3 H 0.776007 0.825781 0.361615 0.021 Uiso 1 1 calc R U . . .
C9 C 0.06259(11) 0.67688(11) 0.19983(10) 0.01834(17) Uani 1 1 d . . . . .
H9 H 0.044144 0.664397 0.095745 0.022 Uiso 1 1 calc R U . . .
O2 O 1.09543(10) 1.31327(10) 0.14584(9) 0.02952(18) Uani 1 1 d . . . . .
C7 C 0.49638(11) 0.84754(10) 0.32967(9) 0.01698(17) Uani 1 1 d . . . . .
C5 C 0.64485(10) 1.04116(10) 0.20818(10) 0.01782(17) Uani 1 1 d . . . . .
C4 C 0.64181(10) 0.93073(10) 0.28322(9) 0.01573(16) Uani 1 1 d . . . . .
C2 C 0.91562(10) 0.97860(10) 0.27136(10) 0.01813(17) Uani 1 1 d . . . . .
H2 H 1.004852 0.956442 0.289397 0.022 Uiso 1 1 calc R U . . .
C6 C 0.78321(11) 1.12350(11) 0.16875(10) 0.01861(17) Uani 1 1 d . . . . .
C1 C 0.91690(10) 1.09084(10) 0.20220(9) 0.01704(17) Uani 1 1 d . . . . .
C15 C -0.26622(11) 0.49375(11) 0.10442(10) 0.01952(18) Uani 1 1 d . . . . .
H15 H -0.281551 0.485879 0.002009 0.023 Uiso 1 1 calc R U . . .
C10 C -0.09278(10) 0.59046(10) 0.23126(9) 0.01649(17) Uani 1 1 d . . . . .
C12 C -0.22065(11) 0.51693(11) 0.41110(10) 0.01921(18) Uani 1 1 d . . . . .
H12 H -0.205798 0.524328 0.513301 0.023 Uiso 1 1 calc R U . . .
C11 C -0.07117(10) 0.60184(10) 0.38541(10) 0.01762(17) Uani 1 1 d . . . . .
H11 H 0.043566 0.666417 0.470486 0.021 Uiso 1 1 calc R U . . .
C8 C 0.51905(12) 0.77092(12) 0.44634(11) 0.02224(18) Uani 1 1 d . . . . .
H8A H 0.443795 0.768908 0.498626 0.033 Uiso 1 1 calc R U . . .
H8B H 0.642331 0.843594 0.526592 0.033 Uiso 1 1 calc R U . . .
H8C H 0.485499 0.651285 0.388385 0.033 Uiso 1 1 calc R U . . .
C14 C -0.41609(11) 0.40916(11) 0.13107(10) 0.02050(18) Uani 1 1 d . . . . .
H14 H -0.531086 0.345320 0.046590 0.025 Uiso 1 1 calc R U . . .
C13 C -0.39353(11) 0.42029(10) 0.28400(10) 0.01971(18) Uani 1 1 d . . . . .
H13 H -0.493421 0.363460 0.301689 0.024 Uiso 1 1 calc R U . . .
H5 H 0.5474(18) 1.0620(17) 0.1847(16) 0.028(3) Uiso 1 1 d . . . . .
H6 H 0.7833(19) 1.2010(19) 0.1196(18) 0.034(3) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 N2 1.3997(10) . ?
N3 C9 1.2786(11) . ?
O1 N1 1.2321(10) . ?
N2 C7 1.2921(11) . ?
N1 O2 1.2312(10) . ?
N1 C1 1.4675(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.4001(11) . ?
C3 C2 1.3903(11) . ?
C9 H9 0.9300 . ?
C9 C10 1.4662(11) . ?
C7 C4 1.4823(11) . ?
C7 C8 1.5020(11) . ?
C5 C4 1.4062(11) . ?
C5 C6 1.3856(11) . ?
C5 H5 0.995(13) . ?
C2 H2 0.9300 . ?
C2 C1 1.3849(11) . ?
C6 C1 1.3918(11) . ?
C6 H6 0.967(14) . ?
C15 H15 0.9300 . ?
C15 C10 1.4000(11) . ?
C15 C14 1.3948(12) . ?
C10 C11 1.4034(11) . ?
C12 H12 0.9300 . ?
C12 C11 1.3868(11) . ?
C12 C13 1.3978(11) . ?
C11 H11 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C14 H14 0.9300 . ?
C14 C13 1.3909(12) . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N3 N2 113.04(7) . . ?
C7 N2 N3 113.96(7) . . ?
O1 N1 C1 118.12(7) . . ?
O2 N1 O1 123.80(8) . . ?
O2 N1 C1 118.06(7) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.67(7) . . ?
N3 C9 H9 119.5 . . ?
N3 C9 C10 121.06(7) . . ?
C10 C9 H9 119.5 . . ?
N2 C7 C4 115.99(7) . . ?
N2 C7 C8 124.28(8) . . ?
C4 C7 C8 119.70(7) . . ?
C4 C5 H5 119.6(8) . . ?
C6 C5 C4 120.84(7) . . ?
C6 C5 H5 119.6(8) . . ?
C3 C4 C7 120.31(7) . . ?
C3 C4 C5 119.13(7) . . ?
C5 C4 C7 120.56(7) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 C3 118.46(7) . . ?
C1 C2 H2 120.8 . . ?
C5 C6 C1 118.21(7) . . ?
C5 C6 H6 119.0(9) . . ?
C1 C6 H6 122.8(9) . . ?
C2 C1 N1 117.93(7) . . ?
C2 C1 C6 122.64(7) . . ?
C6 C1 N1 119.41(7) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C10 120.25(8) . . ?
C15 C10 C9 119.22(7) . . ?
C15 C10 C11 119.41(7) . . ?
C11 C10 C9 121.38(7) . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.27(8) . . ?
C13 C12 H12 119.9 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.10(7) . . ?
C12 C11 H11 119.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 119.99(7) . . ?
C13 C14 H14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 119.97(8) . . ?
C14 C13 H13 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 N2 C7 C4 -177.68(6) . . . . ?
N3 N2 C7 C8 4.16(12) . . . . ?
N3 C9 C10 C15 178.68(7) . . . . ?
N3 C9 C10 C11 -1.70(12) . . . . ?
O1 N1 C1 C2 16.26(11) . . . . ?
O1 N1 C1 C6 -165.68(8) . . . . ?
N2 N3 C9 C10 -179.50(6) . . . . ?
N2 C7 C4 C3 -162.21(8) . . . . ?
N2 C7 C4 C5 17.60(11) . . . . ?
C3 C2 C1 N1 176.07(7) . . . . ?
C3 C2 C1 C6 -1.93(12) . . . . ?
C9 N3 N2 C7 -143.96(8) . . . . ?
C9 C10 C11 C12 -179.23(7) . . . . ?
O2 N1 C1 C2 -162.25(8) . . . . ?
O2 N1 C1 C6 15.82(11) . . . . ?
C5 C6 C1 N1 -177.31(6) . . . . ?
C5 C6 C1 C2 0.66(12) . . . . ?
C4 C3 C2 C1 1.18(12) . . . . ?
C4 C5 C6 C1 1.37(12) . . . . ?
C2 C3 C4 C7 -179.42(7) . . . . ?
C2 C3 C4 C5 0.77(12) . . . . ?
C6 C5 C4 C3 -2.07(12) . . . . ?
C6 C5 C4 C7 178.11(7) . . . . ?
C15 C10 C11 C12 0.39(11) . . . . ?
C15 C14 C13 C12 0.29(12) . . . . ?
C10 C15 C14 C13 -0.18(12) . . . . ?
C11 C12 C13 C14 -0.05(12) . . . . ?
C8 C7 C4 C3 16.04(10) . . . . ?
C8 C7 C4 C5 -164.15(8) . . . . ?
C14 C15 C10 C9 179.47(7) . . . . ?
C14 C15 C10 C11 -0.15(12) . . . . ?
C13 C12 C11 C10 -0.28(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
