# Supplementary Information (SI) for Dalton Transactions.
# 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_12mara_o_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2371545'
loop_
_audit_author_name
_audit_author_address
Srinivas
;IIT Kanpur
India
;
_audit_update_record             
;
2024-08-08 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;
_audit_creation_date             2024-08-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H2 F3 N5.969 O2, H2 O, H5 N2'
_chemical_formula_sum            'C6 H9 F3 N8 O3'
_chemical_formula_weight         298.21
_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'
F F 0.0171 0.0103 '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'

_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                   7.408(3)
_cell_length_b                   19.158(6)
_cell_length_c                   8.467(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.839(11)
_cell_angle_gamma                90
_cell_volume                     1115.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4939
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.80
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18295
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.385
_diffrn_reflns_theta_min         2.126
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2155
_reflns_number_total             2776
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2776
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.070
_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)+(0.0464P)²+0.9184P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1191
_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,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2)
;
_atom_sites_solution_hydrogens   mixed
_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
F1 F 0.53898(19) 0.44102(6) 0.76520(16) 0.0254(3) Uani 1 1 d . . . . .
F2 F 0.6277(2) 0.38257(7) 0.99997(15) 0.0260(3) Uani 1 1 d . . . . .
F3 F 0.83989(18) 0.41908(7) 0.90290(16) 0.0250(3) Uani 1 1 d . . . . .
O2 O 0.6896(2) 0.04264(7) 0.34686(19) 0.0226(3) Uani 1 1 d . . . . .
O1 O 0.7542(2) 0.42827(8) 0.42107(19) 0.0220(3) Uani 1 1 d G . . . .
H1A H 0.759988 0.469249 0.466834 0.033 Uiso 1 1 d G U . . .
H1B H 0.735370 0.396688 0.487325 0.033 Uiso 1 1 d G U . . .
O3 O 0.7674(2) 0.09588(8) 0.59021(18) 0.0209(3) Uani 1 1 d . . . . .
N2 N 0.6584(2) 0.16418(9) 0.1869(2) 0.0153(3) Uani 1 1 d . . . . .
N3 N 0.7109(2) 0.09579(9) 0.4336(2) 0.0142(5) Uani 0.969(7) 1 d . . . . .
N7 N 0.6194(2) 0.23123(9) 0.1427(2) 0.0150(3) Uani 1 1 d . . . . .
N1 N 0.6066(2) 0.26415(9) 0.8172(2) 0.0156(3) Uani 1 1 d . . . . .
N8 N 0.5992(2) 0.21683(9) 0.6920(2) 0.0145(3) Uani 1 1 d . . . . .
N5 N 0.5409(3) 0.08307(10) 0.7969(2) 0.0183(4) Uani 1 1 d . . . . .
N4 N 0.6564(2) 0.32275(8) 0.6064(2) 0.0139(3) Uani 1 1 d . . . . .
C5 C 0.6405(3) 0.32510(10) 0.7596(2) 0.0135(4) Uani 1 1 d . . . . .
C6 C 0.6606(3) 0.39167(11) 0.8565(2) 0.0160(4) Uani 1 1 d . . . . .
C2 C 0.6035(3) 0.27051(10) 0.2684(2) 0.0150(4) Uani 1 1 d . . . . .
H2 H 0.575673 0.319063 0.262207 0.018 Uiso 1 1 calc R U . . .
N6 N 0.7241(3) 0.06453(10) 0.9297(2) 0.0206(4) Uani 1 1 d . . . . .
H6A H 0.819(4) 0.0745(13) 0.899(3) 0.025 Uiso 1 1 d . U . . .
H6B H 0.729(4) 0.0929(13) 1.015(3) 0.025 Uiso 1 1 d . U . . .
C4 C 0.6306(3) 0.25378(10) 0.5706(2) 0.0125(4) Uani 1 1 d . . . . .
C1 C 0.6673(3) 0.16231(10) 0.3474(2) 0.0132(4) Uani 1 1 d . . . . .
C3 C 0.6349(3) 0.22792(10) 0.4089(2) 0.0130(4) Uani 1 1 d . . . . .
H5A H 0.506(3) 0.0474(12) 0.712(3) 0.016 Uiso 1 1 d . U . . .
H5B H 0.441(3) 0.0849(12) 0.839(3) 0.016 Uiso 1 1 d . U . . .
H7 H 0.615(4) 0.2447(15) 0.039(4) 0.037(8) Uiso 1 1 d . . . . .
H5C H 0.550(4) 0.1277(15) 0.748(3) 0.034(7) 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
F1 C6 1.336(2) . ?
F2 C6 1.336(2) . ?
F3 C6 1.344(2) . ?
O2 N3 1.231(2) . ?
O1 H1A 0.8695 . ?
O1 H1B 0.8708 . ?
O3 N3 1.233(2) . ?
N2 N7 1.339(2) . ?
N2 C1 1.336(2) . ?
N3 C1 1.444(2) . ?
N7 C2 1.344(2) . ?
N7 H7 0.90(3) . ?
N1 N8 1.380(2) . ?
N1 C5 1.325(3) . ?
N8 C4 1.338(2) . ?
N5 N6 1.448(3) . ?
N5 H5A 0.95(2) . ?
N5 H5B 0.93(2) . ?
N5 H5C 0.96(3) . ?
N4 C5 1.346(2) . ?
N4 C4 1.353(2) . ?
C5 C6 1.494(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(3) . ?
N6 H6A 0.85(3) . ?
N6 H6B 0.90(3) . ?
C4 C3 1.467(2) . ?
C1 C3 1.415(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A O1 H1B 109.5 . . ?
C1 N2 N7 103.54(15) . . ?
O2 N3 O3 124.04(17) . . ?
O2 N3 C1 118.26(16) . . ?
O3 N3 C1 117.70(16) . . ?
N2 N7 C2 112.89(16) . . ?
N2 N7 H7 118.1(18) . . ?
C2 N7 H7 128.8(18) . . ?
C5 N1 N8 104.76(15) . . ?
C4 N8 N1 105.91(15) . . ?
N6 N5 H5A 108.7(14) . . ?
N6 N5 H5B 111.2(14) . . ?
N6 N5 H5C 110.9(17) . . ?
H5A N5 H5B 106.4(19) . . ?
H5A N5 H5C 111(2) . . ?
H5B N5 H5C 109(2) . . ?
C5 N4 C4 101.12(15) . . ?
N1 C5 N4 114.96(17) . . ?
N1 C5 C6 122.94(17) . . ?
N4 C5 C6 122.11(17) . . ?
F1 C6 F3 105.84(16) . . ?
F1 C6 C5 112.22(16) . . ?
F2 C6 F1 107.86(16) . . ?
F2 C6 F3 106.26(16) . . ?
F2 C6 C5 111.94(16) . . ?
F3 C6 C5 112.32(16) . . ?
N7 C2 H2 125.9 . . ?
N7 C2 C3 108.26(17) . . ?
C3 C2 H2 125.9 . . ?
N5 N6 H6A 110.3(18) . . ?
N5 N6 H6B 103.0(16) . . ?
H6A N6 H6B 109(2) . . ?
N8 C4 N4 113.25(16) . . ?
N8 C4 C3 127.48(17) . . ?
N4 C4 C3 119.25(16) . . ?
N2 C1 N3 117.05(16) . . ?
N2 C1 C3 113.56(17) . . ?
C3 C1 N3 129.38(17) . . ?
C2 C3 C4 123.09(17) . . ?
C2 C3 C1 101.75(16) . . ?
C1 C3 C4 135.17(17) . . ?

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
O2 N3 C1 N2 -17.8(3) . . . . ?
O2 N3 C1 C3 163.42(19) . . . . ?
O3 N3 C1 N2 162.17(17) . . . . ?
O3 N3 C1 C3 -16.6(3) . . . . ?
N2 N7 C2 C3 0.4(2) . . . . ?
N2 C1 C3 C2 0.4(2) . . . . ?
N2 C1 C3 C4 -179.4(2) . . . . ?
N3 C1 C3 C2 179.20(19) . . . . ?
N3 C1 C3 C4 -0.6(4) . . . . ?
N7 N2 C1 N3 -179.14(16) . . . . ?
N7 N2 C1 C3 -0.2(2) . . . . ?
N7 C2 C3 C4 179.34(17) . . . . ?
N7 C2 C3 C1 -0.5(2) . . . . ?
N1 N8 C4 N4 -0.6(2) . . . . ?
N1 N8 C4 C3 -179.18(18) . . . . ?
N1 C5 C6 F1 -125.5(2) . . . . ?
N1 C5 C6 F2 -4.1(3) . . . . ?
N1 C5 C6 F3 115.4(2) . . . . ?
N8 N1 C5 N4 0.0(2) . . . . ?
N8 N1 C5 C6 -179.74(17) . . . . ?
N8 C4 C3 C2 157.7(2) . . . . ?
N8 C4 C3 C1 -22.6(4) . . . . ?
N4 C5 C6 F1 54.7(2) . . . . ?
N4 C5 C6 F2 176.17(17) . . . . ?
N4 C5 C6 F3 -64.4(2) . . . . ?
N4 C4 C3 C2 -20.8(3) . . . . ?
N4 C4 C3 C1 159.0(2) . . . . ?
C5 N1 N8 C4 0.4(2) . . . . ?
C5 N4 C4 N8 0.6(2) . . . . ?
C5 N4 C4 C3 179.29(17) . . . . ?
C4 N4 C5 N1 -0.4(2) . . . . ?
C4 N4 C5 C6 179.39(18) . . . . ?
C1 N2 N7 C2 -0.1(2) . . . . ?

_smtbx_masks_void_probe_radius   2.0
_smtbx_masks_void_truncation_radius 2.0
_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_17maya_b
_database_code_depnum_ccdc_archive 'CCDC 2371546'
loop_
_audit_author_name
_audit_author_address
Srinivas
;IIT Kanpur
India
;
_audit_update_record             
;
2024-07-17 deposited with the CCDC.	2024-08-19 downloaded from the CCDC.
;
_audit_creation_date             2024-07-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_formula_moiety         'C6 H2 F3 N5 O3'
_chemical_formula_sum            'C6 H2 F3 N5 O3'
_chemical_formula_weight         249.110
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   15.7760(15)
_cell_length_b                   7.3324(6)
_cell_length_c                   7.5674(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.769(3)
_cell_angle_gamma                90
_cell_volume                     870.93(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6544
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.346
_cell_measurement_theta_min      2.595
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6598
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_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    1.900
_exptl_crystal_description       needle
_exptl_crystal_F_000             496.425
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.9975
_diffrn_reflns_Laue_measured_fraction_max 0.9954
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13853
_diffrn_reflns_point_group_measured_fraction_full 0.9975
_diffrn_reflns_point_group_measured_fraction_max 0.9954
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         2.60
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.9954
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              21
_reflns_limit_h_min              -21
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                1887
_reflns_number_total             2177
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.3189
_refine_diff_density_min         -0.3028
_refine_diff_density_rms         0.0586
_refine_ls_d_res_high            0.7472
_refine_ls_d_res_low             7.8480
_refine_ls_goodness_of_fit_ref   1.1061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    2
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.1061
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0346P)²+0.4218P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0888
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2. Others
 Fixed Sof: F3(0.5) F2(0.5) F1(0.5) F5(0.5) F6(0.5) F4(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
O1 O 0.81110(6) 0.84067(13) 0.52480(11) 0.0205(2) Uani 1.000000 .
O2 O 0.92129(6) 0.89917(13) 0.38451(14) 0.0267(2) Uani 1.000000 .
O3 O 0.61040(7) 0.40794(18) 0.54709(14) 0.0361(3) Uani 1.000000 .
N3 N 0.86934(6) 0.79365(14) 0.44033(13) 0.0175(2) Uani 1.000000 .
F3 F 0.6329(4) 0.4960(7) 0.9904(7) 0.0468(13) Uani 0.500000 .
N1 N 0.93218(7) 0.36968(15) 0.30213(14) 0.0197(2) Uani 1.000000 .
H1 H 0.96763(7) 0.29770(15) 0.25255(14) 0.0236(3) Uiso 1.000000 R
N4 N 0.72854(7) 0.53312(16) 0.67408(14) 0.0206(2) Uani 1.000000 .
N2 N 0.94460(7) 0.54971(15) 0.32304(13) 0.0180(2) Uani 1.000000 .
N5 N 0.67292(8) 0.3831(2) 0.42840(17) 0.0344(3) Uani 1.000000 .
C3 C 0.87774(8) 0.60231(17) 0.40259(15) 0.0160(2) Uani 1.000000 .
C4 C 0.74030(8) 0.45959(18) 0.51016(16) 0.0190(3) Uani 1.000000 .
C2 C 0.82140(8) 0.45943(17) 0.43292(15) 0.0175(2) Uani 1.000000 .
F2 F 0.60421(15) 0.7440(4) 0.8554(4) 0.0356(6) Uani 0.500000 .
C1 C 0.86014(8) 0.30989(18) 0.36441(17) 0.0203(3) Uani 1.000000 .
F1 F 0.51950(17) 0.5220(4) 0.8071(4) 0.0477(8) Uani 0.500000 .
C5 C 0.64956(8) 0.4972(2) 0.68465(18) 0.0236(3) Uani 1.000000 .
C6 C 0.59765(10) 0.5535(2) 0.8331(2) 0.0323(3) Uani 1.000000 .
F5 F 0.5627(3) 0.7040(5) 0.7945(6) 0.0984(16) Uani 0.500000 .
F6 F 0.6387(3) 0.5383(9) 0.9825(6) 0.0681(18) Uani 0.500000 .
H1a H 0.8426(11) 0.187(3) 0.361(2) 0.030(4) Uiso 1.000000 .
F4 F 0.53155(17) 0.4262(4) 0.8357(4) 0.0383(6) Uani 0.500000 .


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 N3 1.2205(13) . ?
O2 N3 1.2322(14) . ?
O3 N5 1.4110(15) . ?
O3 C5 1.3282(17) . ?
N3 C3 1.4405(16) . ?
F3 C6 1.331(5) . ?
F3 F6 0.330(10) . ?
N1 N2 1.3416(16) . ?
N1 C1 1.3467(17) . ?
N4 C4 1.3820(16) . ?
N4 C5 1.2839(17) . ?
N2 C3 1.3234(15) . ?
N5 C4 1.3019(18) . ?
C3 C2 1.4076(17) . ?
C4 C2 1.4591(17) . ?
C2 C1 1.3814(18) . ?
F2 C6 1.409(3) . ?
F2 F5 0.816(5) . ?
F1 C6 1.250(3) . ?
F1 F5 1.506(5) . ?
F1 F4 0.754(3) . ?
C5 C6 1.5126(19) . ?
C6 F5 1.254(4) . ?
C6 F6 1.250(5) . ?
C6 F4 1.401(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O3 N5 105.23(10) . . ?
O2 N3 O1 124.32(11) . . ?
C3 N3 O1 117.91(10) . . ?
C3 N3 O2 117.77(10) . . ?
F6 F3 C6 68.8(15) . . ?
C1 N1 N2 113.42(11) . . ?
C5 N4 C4 101.22(11) . . ?
C3 N2 N1 103.10(10) . . ?
C4 N5 O3 103.38(11) . . ?
N2 C3 N3 117.87(11) . . ?
C2 C3 N3 128.35(11) . . ?
C2 C3 N2 113.73(11) . . ?
N5 C4 N4 114.69(12) . . ?
C2 C4 N4 124.20(11) . . ?
C2 C4 N5 121.08(11) . . ?
C4 C2 C3 131.16(12) . . ?
C1 C2 C3 102.66(11) . . ?
C1 C2 C4 126.15(12) . . ?
F5 F2 C6 62.0(4) . . ?
C2 C1 N1 107.08(12) . . ?
F5 F1 C6 53.2(2) . . ?
F4 F1 C6 84.9(4) . . ?
F4 F1 F5 137.8(5) . . ?
N4 C5 O3 115.48(12) . . ?
C6 C5 O3 118.20(12) . . ?
C6 C5 N4 126.27(13) . . ?
F2 C6 F3 100.8(3) . . ?
F1 C6 F3 113.6(3) . . ?
F1 C6 F2 105.1(2) . . ?
C5 C6 F3 111.6(3) . . ?
C5 C6 F2 108.71(16) . . ?
C5 C6 F1 115.57(18) . . ?
F5 C6 F3 128.4(4) . . ?
F5 C6 F2 35.1(2) . . ?
F5 C6 F1 73.9(3) . . ?
F5 C6 C5 109.0(2) . . ?
F6 C6 F3 14.2(5) . . ?
F6 C6 F2 87.4(3) . . ?
F6 C6 F1 122.6(3) . . ?
F6 C6 C5 112.2(3) . . ?
F6 C6 F5 117.7(4) . . ?
F4 C6 F3 91.2(3) . . ?
F4 C6 F2 134.77(19) . . ?
F4 C6 F1 32.41(15) . . ?
F4 C6 C5 106.74(16) . . ?
F4 C6 F5 106.2(3) . . ?
F4 C6 F6 104.2(3) . . ?
F1 F5 F2 128.7(6) . . ?
C6 F5 F2 82.9(5) . . ?
C6 F5 F1 52.9(2) . . ?
C6 F6 F3 96.9(16) . . ?
C6 F4 F1 62.7(3) . . ?

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
O1 N3 C3 N2 -174.91(10) . . . . ?
O1 N3 C3 C2 7.94(13) . . . . ?
O2 N3 C3 N2 5.37(12) . . . . ?
O2 N3 C3 C2 -171.78(11) . . . . ?
O3 N5 C4 N4 0.25(14) . . . . ?
O3 N5 C4 C2 178.32(10) . . . . ?
O3 C5 N4 C4 0.63(14) . . . . ?
O3 C5 C6 F3 126.8(3) . . . . ?
O3 C5 C6 F2 -122.90(17) . . . . ?
O3 C5 C6 F1 -5.0(2) . . . . ?
O3 C5 C6 F5 -85.8(3) . . . . ?
O3 C5 C6 F6 142.1(3) . . . . ?
O3 C5 C6 F4 28.53(18) . . . . ?
N3 C3 N2 N1 -177.99(11) . . . . ?
N3 C3 C2 C4 -0.49(16) . . . . ?
N3 C3 C2 C1 177.50(14) . . . . ?
F3 C6 F2 F5 -145.9(6) . . . . ?
F3 C6 F1 F5 125.4(5) . . . . ?
F3 C6 F1 F4 -50.0(5) . . . . ?
F3 C6 C5 N4 -56.0(3) . . . . ?
F3 C6 F5 F2 44.6(5) . . . . ?
F3 C6 F5 F1 -107.6(5) . . . . ?
F3 C6 F4 F1 135.4(6) . . . . ?
F3 F6 C6 F2 160(2) . . . . ?
F3 F6 C6 F1 54(2) . . . . ?
F3 F6 C6 C5 -91(2) . . . . ?
F3 F6 C6 F5 142(2) . . . . ?
F3 F6 C6 F4 24(2) . . . . ?
N1 N2 C3 C2 -0.42(10) . . . . ?
N1 C1 C2 C3 0.04(11) . . . . ?
N1 C1 C2 C4 178.17(9) . . . . ?
N4 C4 C2 C3 -53.54(16) . . . . ?
N4 C4 C2 C1 128.89(13) . . . . ?
N4 C5 C6 F2 54.30(18) . . . . ?
N4 C5 C6 F1 172.2(2) . . . . ?
N4 C5 C6 F5 91.4(3) . . . . ?
N4 C5 C6 F6 -40.7(3) . . . . ?
N4 C5 C6 F4 -154.3(2) . . . . ?
N2 C3 C2 C4 -177.74(10) . . . . ?
N2 C3 C2 C1 0.25(11) . . . . ?
N5 C4 C2 C3 128.58(14) . . . . ?
N5 C4 C2 C1 -48.99(16) . . . . ?
F2 C6 F1 F5 16.1(3) . . . . ?
F2 C6 F1 F4 -159.2(5) . . . . ?
F2 C6 F5 F1 -152.2(3) . . . . ?
F2 C6 F4 F1 28.8(4) . . . . ?
F2 F5 F1 C6 -36.4(5) . . . . ?
F2 F5 F1 F4 -29.5(8) . . . . ?
F2 F5 C6 F1 152.2(5) . . . . ?
F2 F5 C6 C5 -95.8(4) . . . . ?
F2 F5 C6 F6 33.4(5) . . . . ?
F2 F5 C6 F4 149.6(4) . . . . ?
F1 F5 C6 C5 112.07(17) . . . . ?
F1 F5 C6 F6 -118.8(3) . . . . ?
F1 F5 C6 F4 -2.6(2) . . . . ?
F1 F4 C6 C5 -111.5(4) . . . . ?
F1 F4 C6 F5 4.6(5) . . . . ?
F1 F4 C6 F6 129.6(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
