# Supplementary Information (SI) for Green Chemistry.
# 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_hmj_a
_audit_block_doi                 10.5517/ccdc.csd.cc2g0n27
_database_code_depnum_ccdc_archive 'CCDC 2264738'
loop_
_audit_author_name
_audit_author_address
HMJ-Oxadiazole
;Nanjing University
China
;
_audit_update_record             
;
2023-05-23 deposited with the CCDC.	2024-11-25 downloaded from the CCDC.
;
_audit_creation_date             2023-05-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C10 H8 F3 N3 O)'
_chemical_formula_sum            'C20 H16 F6 N6 O2'
_chemical_formula_weight         486.39
_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 0.0148 0.0070 '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'
F F 0.0599 0.0411 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.900(3)
_cell_length_b                   12.748(6)
_cell_length_c                   28.745(15)
_cell_angle_alpha                90
_cell_angle_beta                 95.113(19)
_cell_angle_gamma                90
_cell_volume                     2153.3(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4557
_cell_measurement_temperature    193.0
_cell_measurement_theta_max      48.09
_cell_measurement_theta_min      2.69
_shelx_estimated_absorpt_T_max   0.927
_shelx_estimated_absorpt_T_min   0.927
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_correction_T_min  0.5961
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1383 before and 0.0899 after correction.
The Ratio of minimum to maximum transmission is 0.7942.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0995
_diffrn_reflns_av_unetI/netI     0.0935
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            26562
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.972
_diffrn_reflns_theta_min         2.685
_diffrn_ambient_temperature      193.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2396
_reflns_number_total             3932
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3932
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0641
_refine_ls_restrained_S_all      1.024
_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)+(0.0901P)²+0.3134P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1601
_refine_ls_wR_factor_ref         0.1915
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N4(H4A), C6(H6), C12(H12), C2(H2), C3(H3), C16(H16), C5(H5), C4(H4),
 C13(H13), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O1 O 0.1984(3) 0.83701(16) 0.48277(6) 0.0562(5) Uani 1 1 d . . . . .
O2 O 0.5980(3) 0.51497(16) 0.60550(7) 0.0577(5) Uani 1 1 d . . . . .
F6 F 0.2708(4) 0.5193(2) 0.51930(7) 0.1003(8) Uani 1 1 d . . . . .
F1 F -0.0775(4) 0.8017(2) 0.39525(7) 0.1051(8) Uani 1 1 d . . . . .
F3 F -0.0085(4) 0.66390(18) 0.43515(8) 0.1032(8) Uani 1 1 d . . . . .
F2 F -0.3326(4) 0.7389(2) 0.43441(8) 0.1088(8) Uani 1 1 d . . . . .
N1 N 0.4205(4) 0.9225(2) 0.54087(8) 0.0585(7) Uani 1 1 d . . . . .
H1 H 0.5349 0.9177 0.5233 0.070 Uiso 1 1 calc R . . . .
N4 N 0.8254(4) 0.4398(2) 0.66585(8) 0.0603(7) Uani 1 1 d . . . . .
H4A H 0.9396 0.4439 0.6482 0.072 Uiso 1 1 calc R . . . .
N3 N -0.1410(4) 0.8574(2) 0.50801(9) 0.0594(7) Uani 1 1 d . . . . .
N2 N 0.0173(4) 0.9071(2) 0.54056(8) 0.0567(6) Uani 1 1 d . . . . .
N5 N 0.4240(4) 0.4553(2) 0.66625(9) 0.0616(7) Uani 1 1 d . . . . .
N6 N 0.2628(4) 0.4994(2) 0.63279(10) 0.0669(7) Uani 1 1 d . . . . .
F4 F 0.4029(6) 0.6625(2) 0.54414(10) 0.1431(12) Uani 1 1 d . . . . .
C8 C 0.2149(5) 0.8918(2) 0.52399(9) 0.0512(7) Uani 1 1 d . . . . .
C18 C 0.6187(5) 0.4673(2) 0.64842(10) 0.0541(7) Uani 1 1 d . . . . .
C11 C 0.8648(5) 0.4888(2) 0.74988(10) 0.0545(7) Uani 1 1 d . . . . .
C1 C 0.4792(5) 0.8782(2) 0.62475(10) 0.0528(7) Uani 1 1 d . . . . .
C6 C 0.6705(5) 0.8150(3) 0.63014(11) 0.0596(8) Uani 1 1 d . . . . .
H6 H 0.7901 0.8251 0.6106 0.072 Uiso 1 1 calc R . . . .
C9 C -0.0295(5) 0.8193(2) 0.47592(10) 0.0556(7) Uani 1 1 d . . . . .
C12 C 0.6873(5) 0.4981(2) 0.77809(11) 0.0597(8) Uani 1 1 d . . . . .
H12 H 0.5634 0.4504 0.7743 0.072 Uiso 1 1 calc R . . . .
C2 C 0.3054(5) 0.8610(2) 0.65341(10) 0.0578(8) Uani 1 1 d . . . . .
H2 H 0.1722 0.9031 0.6499 0.069 Uiso 1 1 calc R . . . .
F5 F 0.0692(5) 0.6145(3) 0.55809(9) 0.1570(14) Uani 1 1 d . . . . .
C17 C 0.8664(5) 0.4027(3) 0.71408(10) 0.0612(8) Uani 1 1 d . . . . .
H17A H 1.0157 0.3668 0.7178 0.073 Uiso 1 1 calc R . . . .
H17B H 0.7482 0.3505 0.7201 0.073 Uiso 1 1 calc R . . . .
C19 C 0.3697(5) 0.5325(3) 0.59924(11) 0.0615(8) Uani 1 1 d . . . . .
C7 C 0.4599(5) 0.9642(2) 0.58814(10) 0.0605(8) Uani 1 1 d . . . . .
H7A H 0.3329 1.0115 0.5943 0.073 Uiso 1 1 calc R . . . .
H7B H 0.6018 1.0060 0.5907 0.073 Uiso 1 1 calc R . . . .
C3 C 0.3241(5) 0.7833(3) 0.68694(11) 0.0645(8) Uani 1 1 d . . . . .
H3 H 0.2044 0.7725 0.7064 0.077 Uiso 1 1 calc R . . . .
C16 C 1.0423(5) 0.5601(3) 0.75616(11) 0.0639(8) Uani 1 1 d . . . . .
H16 H 1.1654 0.5554 0.7371 0.077 Uiso 1 1 calc R . . . .
C5 C 0.6891(5) 0.7370(3) 0.66383(11) 0.0641(8) Uani 1 1 d . . . . .
H5 H 0.8214 0.6942 0.6673 0.077 Uiso 1 1 calc R . . . .
C4 C 0.5163(6) 0.7214(3) 0.69222(11) 0.0667(9) Uani 1 1 d . . . . .
H4 H 0.5294 0.6681 0.7154 0.080 Uiso 1 1 calc R . . . .
C13 C 0.6876(6) 0.5753(3) 0.81145(11) 0.0689(9) Uani 1 1 d . . . . .
H13 H 0.5644 0.5804 0.8305 0.083 Uiso 1 1 calc R . . . .
C14 C 0.8654(6) 0.6452(3) 0.81744(11) 0.0712(9) Uani 1 1 d . . . . .
H14 H 0.8658 0.6983 0.8406 0.085 Uiso 1 1 calc R . . . .
C10 C -0.1133(6) 0.7558(3) 0.43522(12) 0.0717(9) Uani 1 1 d . . . . .
C15 C 1.0432(6) 0.6376(3) 0.78949(12) 0.0708(9) Uani 1 1 d . . . . .
H15 H 1.1661 0.6858 0.7933 0.085 Uiso 1 1 calc R . . . .
C20 C 0.2771(7) 0.5829(3) 0.55516(13) 0.0808(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.371(3) . ?
O1 C9 1.360(3) . ?
O2 C18 1.371(3) . ?
O2 C19 1.362(4) . ?
F6 C20 1.309(4) . ?
F1 C10 1.323(4) . ?
F3 C10 1.325(4) . ?
F2 C10 1.310(4) . ?
N1 C8 1.325(4) . ?
N1 C7 1.458(4) . ?
N4 C18 1.324(4) . ?
N4 C17 1.465(4) . ?
N3 N2 1.412(3) . ?
N3 C9 1.276(4) . ?
N2 C8 1.313(4) . ?
N5 N6 1.408(4) . ?
N5 C18 1.308(4) . ?
N6 C19 1.270(4) . ?
F4 C20 1.313(5) . ?
C11 C12 1.385(4) . ?
C11 C17 1.505(4) . ?
C11 C16 1.386(4) . ?
C1 C6 1.385(4) . ?
C1 C2 1.389(4) . ?
C1 C7 1.516(4) . ?
C6 C5 1.385(4) . ?
C9 C10 1.472(5) . ?
C12 C13 1.374(4) . ?
C2 C3 1.379(4) . ?
F5 C20 1.301(5) . ?
C19 C20 1.481(5) . ?
C3 C4 1.378(5) . ?
C16 C15 1.376(5) . ?
C5 C4 1.376(4) . ?
C13 C14 1.375(5) . ?
C14 C15 1.380(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C8 101.7(2) . . ?
C19 O2 C18 101.5(2) . . ?
C8 N1 C7 120.9(2) . . ?
C18 N4 C17 120.8(2) . . ?
C9 N3 N2 107.3(2) . . ?
C8 N2 N3 104.4(2) . . ?
C18 N5 N6 104.4(3) . . ?
C19 N6 N5 107.5(3) . . ?
N1 C8 O1 117.3(2) . . ?
N2 C8 O1 113.1(2) . . ?
N2 C8 N1 129.6(3) . . ?
N4 C18 O2 117.6(3) . . ?
N5 C18 O2 113.2(3) . . ?
N5 C18 N4 129.2(3) . . ?
C12 C11 C17 120.9(3) . . ?
C12 C11 C16 118.0(3) . . ?
C16 C11 C17 121.1(3) . . ?
C6 C1 C2 118.6(3) . . ?
C6 C1 C7 120.6(3) . . ?
C2 C1 C7 120.8(3) . . ?
C1 C6 C5 120.6(3) . . ?
O1 C9 C10 117.7(3) . . ?
N3 C9 O1 113.5(3) . . ?
N3 C9 C10 128.7(3) . . ?
C13 C12 C11 121.1(3) . . ?
C3 C2 C1 120.7(3) . . ?
N4 C17 C11 113.7(3) . . ?
O2 C19 C20 118.0(3) . . ?
N6 C19 O2 113.4(3) . . ?
N6 C19 C20 128.6(3) . . ?
N1 C7 C1 112.3(2) . . ?
C4 C3 C2 120.1(3) . . ?
C15 C16 C11 121.2(3) . . ?
C4 C5 C6 120.1(3) . . ?
C5 C4 C3 119.9(3) . . ?
C12 C13 C14 120.3(3) . . ?
C13 C14 C15 119.5(3) . . ?
F1 C10 F3 106.2(3) . . ?
F1 C10 C9 112.2(3) . . ?
F3 C10 C9 111.3(3) . . ?
F2 C10 F1 107.0(3) . . ?
F2 C10 F3 108.4(3) . . ?
F2 C10 C9 111.5(3) . . ?
C16 C15 C14 120.0(3) . . ?
F6 C20 F4 105.4(4) . . ?
F6 C20 C19 112.8(3) . . ?
F4 C20 C19 111.6(3) . . ?
F5 C20 F6 106.4(3) . . ?
F5 C20 F4 109.4(4) . . ?
F5 C20 C19 110.9(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
