# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_C3N6H7CH3SO3H2O
_database_code_depnum_ccdc_archive 'CCDC 2344610'
loop_
_audit_author_name
_audit_author_address
'Hangwei Jia'
;Shihezi University
China
;
_audit_update_record             
;
2024-03-31 deposited with the CCDC.	2024-06-20 downloaded from the CCDC.
;
_audit_creation_date             2024-03-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'melaminium methanesulfonate monohydrate'
_chemical_name_systematic        
'2,4,6-triamino-1,3,5-triazin-1-ium methanesulfonate monohydrate'
_chemical_formula_moiety         'C H3 O3 S, C3 H7 N6, H2 O'
_chemical_formula_sum            'C4 H12 N6 O4 S'
_chemical_formula_weight         240.26
_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'
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'
S S 0.1246 0.1234 '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                   6.5998(9)
_cell_length_b                   6.7955(9)
_cell_length_c                   12.2611(15)
_cell_angle_alpha                76.662(5)
_cell_angle_beta                 85.122(4)
_cell_angle_gamma                71.706(4)
_cell_volume                     507.97(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1425
_cell_measurement_temperature    228.0
_cell_measurement_theta_max      22.79
_cell_measurement_theta_min      3.25
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.843
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6794
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0956 before and 0.0739 after correction.
The Ratio of minimum to maximum transmission is 0.9112.
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    1.571
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.042
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0870
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8526
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.367
_diffrn_reflns_theta_min         1.707
_diffrn_ambient_temperature      228.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_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           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1449
_reflns_number_total             1845
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.06(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1845
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.061
_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)+(0.0390P)²+0.5116P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1323
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1(0.039) H4A(0.048) H4B(0.048) H6A(0.047) H6B(0.047) H4F(0.11)
 H4G(0.11) H5A(0.052) H5B(0.052) H4C(0.078) H4D(0.078) H4E(0.078)
 Fixed X: H1(0.566394) H4A(0.954503) H4B(0.822385) H6A(0.835341) H6B(0.668632)
 H4F(0.483387) H4G(0.6707) H5A(0.255511) H5B(0.301215) H4C(0.7955)
 H4D(0.685598) H4E(0.817837)
 Fixed Y: H1(0.680284) H4A(0.660946) H4B(0.785386) H6A(0.030439) H6B(-
 0.040458) H4F(0.983009) H4G(0.841372) H5A(0.384517) H5B(0.588929)
 H4C(0.433456) H4D(0.262552) H4E(0.229342)
 Fixed Z: H1(0.259555) H4A(0.418424) H4B(0.316546) H6A(0.602099) H6B(0.559018)
 H4F(0.113474) H4G(0.079984) H5A(0.257635) H5B(0.202739) H4C(0.049883)
 H4D(0.11449) H4E(0.002637)
;
_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
S1 S 1.04024(12) 0.14705(12) 0.14833(6) 0.0381(3) Uani 1 1 d . . . . .
N3 N 0.7974(4) 0.3663(4) 0.47190(19) 0.0304(6) Uani 1 1 d . . . . .
N2 N 0.5309(4) 0.2507(4) 0.4045(2) 0.0330(6) Uani 1 1 d . . . . .
O3 O 1.2159(4) 0.1827(4) 0.0741(2) 0.0583(7) Uani 1 1 d . . . . .
N1 N 0.5951(4) 0.5683(4) 0.3139(2) 0.0326(6) Uani 1 1 d . . . . .
H1 H 0.566394 0.680284 0.259555 0.039 Uiso 1 1 calc R U . . .
O2 O 1.0542(4) -0.0742(4) 0.1789(2) 0.0653(8) Uani 1 1 d . . . . .
O1 O 1.0244(4) 0.2412(5) 0.2439(2) 0.0623(8) Uani 1 1 d . . . . .
N4 N 0.8545(4) 0.6762(4) 0.3725(2) 0.0404(7) Uani 1 1 d . . . . .
H4A H 0.954503 0.660946 0.418424 0.048 Uiso 1 1 calc R U . . .
H4B H 0.822385 0.785386 0.316546 0.048 Uiso 1 1 calc R U . . .
N6 N 0.7360(4) 0.0526(4) 0.5544(2) 0.0394(7) Uani 1 1 d . . . . .
H6A H 0.835341 0.030439 0.602099 0.047 Uiso 1 1 calc R U . . .
H6B H 0.668632 -0.040458 0.559018 0.047 Uiso 1 1 calc R U . . .
O4 O 0.5929(4) 0.8762(5) 0.1365(2) 0.0731(10) Uani 1 1 d G . . . .
H4F H 0.483387 0.983009 0.113474 0.110 Uiso 1 1 d G U . . .
H4G H 0.670700 0.841372 0.079984 0.110 Uiso 1 1 d G U . . .
N5 N 0.3293(4) 0.4719(4) 0.2539(2) 0.0431(7) Uani 1 1 d . . . . .
H5A H 0.255511 0.384517 0.257635 0.052 Uiso 1 1 calc R U . . .
H5B H 0.301215 0.588929 0.202739 0.052 Uiso 1 1 calc R U . . .
C1 C 0.7515(4) 0.5336(4) 0.3876(2) 0.0303(7) Uani 1 1 d . . . . .
C2 C 0.4840(4) 0.4269(4) 0.3258(2) 0.0313(7) Uani 1 1 d . . . . .
C3 C 0.6876(4) 0.2272(4) 0.4752(2) 0.0307(7) Uani 1 1 d . . . . .
C4 C 0.8091(6) 0.2833(6) 0.0701(3) 0.0523(9) Uani 1 1 d . . . . .
H4C H 0.795500 0.433456 0.049883 0.078 Uiso 1 1 calc R U . . .
H4D H 0.685598 0.262552 0.114490 0.078 Uiso 1 1 calc R U . . .
H4E H 0.817837 0.229342 0.002637 0.078 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
S1 O3 1.458(2) . ?
S1 O2 1.438(3) . ?
S1 O1 1.441(3) . ?
S1 C4 1.748(3) . ?
N3 C1 1.322(4) . ?
N3 C3 1.352(4) . ?
N2 C2 1.321(4) . ?
N2 C3 1.354(4) . ?
N1 H1 0.8700 . ?
N1 C1 1.358(4) . ?
N1 C2 1.357(4) . ?
N4 H4A 0.8700 . ?
N4 H4B 0.8700 . ?
N4 C1 1.321(4) . ?
N6 H6A 0.8700 . ?
N6 H6B 0.8700 . ?
N6 C3 1.318(4) . ?
O4 H4F 0.8599 . ?
O4 H4G 0.8598 . ?
N5 H5A 0.8700 . ?
N5 H5B 0.8700 . ?
N5 C2 1.322(4) . ?
C4 H4C 0.9700 . ?
C4 H4D 0.9700 . ?
C4 H4E 0.9700 . ?

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
O3 S1 C4 105.35(17) . . ?
O2 S1 O3 111.60(16) . . ?
O2 S1 O1 112.98(18) . . ?
O2 S1 C4 108.28(18) . . ?
O1 S1 O3 111.02(17) . . ?
O1 S1 C4 107.18(17) . . ?
C1 N3 C3 115.4(2) . . ?
C2 N2 C3 115.7(2) . . ?
C1 N1 H1 120.2 . . ?
C2 N1 H1 120.2 . . ?
C2 N1 C1 119.5(3) . . ?
H4A N4 H4B 120.0 . . ?
C1 N4 H4A 120.0 . . ?
C1 N4 H4B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C3 N6 H6A 120.0 . . ?
C3 N6 H6B 120.0 . . ?
H4F O4 H4G 109.5 . . ?
H5A N5 H5B 120.0 . . ?
C2 N5 H5A 120.0 . . ?
C2 N5 H5B 120.0 . . ?
N3 C1 N1 121.7(3) . . ?
N4 C1 N3 121.2(3) . . ?
N4 C1 N1 117.1(3) . . ?
N2 C2 N1 121.5(3) . . ?
N2 C2 N5 121.6(3) . . ?
N5 C2 N1 116.9(3) . . ?
N3 C3 N2 126.0(3) . . ?
N6 C3 N3 117.5(3) . . ?
N6 C3 N2 116.5(3) . . ?
S1 C4 H4C 109.5 . . ?
S1 C4 H4D 109.5 . . ?
S1 C4 H4E 109.5 . . ?
H4C C4 H4D 109.5 . . ?
H4C C4 H4E 109.5 . . ?
H4D C4 H4E 109.5 . . ?

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
C1 N3 C3 N2 -3.7(4) . . . . ?
C1 N3 C3 N6 176.6(2) . . . . ?
C1 N1 C2 N2 -3.2(4) . . . . ?
C1 N1 C2 N5 178.0(3) . . . . ?
C2 N2 C3 N3 0.1(4) . . . . ?
C2 N2 C3 N6 179.8(2) . . . . ?
C2 N1 C1 N3 -0.8(4) . . . . ?
C2 N1 C1 N4 -179.9(2) . . . . ?
C3 N3 C1 N1 4.0(4) . . . . ?
C3 N3 C1 N4 -177.0(3) . . . . ?
C3 N2 C2 N1 3.4(4) . . . . ?
C3 N2 C2 N5 -177.8(3) . . . . ?

_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_C3N6H7BF4H2O
_database_code_depnum_ccdc_archive 'CCDC 2344611'
loop_
_audit_author_name
_audit_author_address
'Hangwei Jia'
;Shihezi University
China
;
_audit_update_record             
;
2024-03-31 deposited with the CCDC.	2024-06-20 downloaded from the CCDC.
;
_audit_creation_date             2024-03-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'melaminium tetrafluoroborate monohydrate'
_chemical_name_systematic        
'2,4,6-triamino-1,3,5-triazin-1-ium tetrafluoroborate monohydrate'
_chemical_formula_moiety         'B F4, C3 H7 N6, H2 O'
_chemical_formula_sum            'C3 H9 B F4 N6 O'
_chemical_formula_weight         231.97
_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'
B B 0.0013 0.0007 '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      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                   5.7474(7)
_cell_length_b                   7.4778(9)
_cell_length_c                   11.7695(14)
_cell_angle_alpha                101.789(5)
_cell_angle_beta                 94.130(5)
_cell_angle_gamma                110.156(5)
_cell_volume                     459.22(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2016
_cell_measurement_temperature    244.00
_cell_measurement_theta_max      24.15
_cell_measurement_theta_min      3.09
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6775
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1158 before and 0.0515 after correction. The Ratio of minimum to maximum transmission is 0.9087. 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    1.678
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.076
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6159
_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         25.342
_diffrn_reflns_theta_min         1.789
_diffrn_ambient_temperature      244.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1226
_reflns_number_total             1644
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.11(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         1644
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0526
_refine_ls_restrained_S_all      1.037
_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)+(0.0651P)²+0.2849P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1480
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O1-H1D
 0.95 with sigma of 0.02
 H1D-O1
 0.95 with sigma of 0.02
 O1-H1C
 0.95 with sigma of 0.02
 H1D-H1D_$1
 2.1 with sigma of 0.02
3. Others
 Sof(F3A)=Sof(F2A)=Sof(F4A)=Sof(F1A)=Sof(B1A)=1-FVAR(1)
 Sof(F3)=Sof(F4)=Sof(F1)=Sof(F2)=Sof(B1)=FVAR(1)
4.a Free rotating group:
 O1(H1C,H1D)
4.b Aromatic/amide H refined with riding coordinates:
 N6(H6)
4.c X=CH2 refined with riding coordinates:
 N3(H3A,H3B), N1(H1A,H1B), N5(H5A,H5B)
;
_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
F3 F 1.1031(7) 0.6246(5) 0.7639(3) 0.0606(9) Uani 0.726(8) 1 d . . P A 1
N4 N 0.6649(4) 0.3286(3) 0.53731(17) 0.0440(6) Uani 1 1 d . . . . .
N6 N 0.5816(4) 0.2601(3) 0.71879(17) 0.0462(6) Uani 1 1 d . . . . .
H6 H 0.510366 0.277142 0.780767 0.055 Uiso 1 1 calc R U . . .
N2 N 0.8198(4) 0.1080(3) 0.61268(17) 0.0448(6) Uani 1 1 d . . . . .
N3 N 0.8925(5) 0.1744(3) 0.43519(18) 0.0549(7) Uani 1 1 d . . . . .
H3A H 0.876420 0.232632 0.379878 0.066 Uiso 1 1 calc R U . . .
H3B H 0.975361 0.095900 0.427431 0.066 Uiso 1 1 calc R U . . .
N1 N 0.7253(5) 0.0499(4) 0.7911(2) 0.0618(7) Uani 1 1 d . . . . .
H1A H 0.805097 -0.030701 0.785405 0.074 Uiso 1 1 calc R U . . .
H1B H 0.654063 0.071383 0.852609 0.074 Uiso 1 1 calc R U . . .
N5 N 0.4361(5) 0.4731(4) 0.6492(2) 0.0613(7) Uani 1 1 d . . . . .
H5A H 0.419663 0.534970 0.595893 0.074 Uiso 1 1 calc R U . . .
H5B H 0.369255 0.489320 0.712680 0.074 Uiso 1 1 calc R U . . .
C3 C 0.5619(5) 0.3548(4) 0.6338(2) 0.0439(6) Uani 1 1 d . . . . .
C2 C 0.7910(4) 0.2051(3) 0.5309(2) 0.0413(6) Uani 1 1 d . . . . .
F4 F 1.1700(7) 0.9382(4) 0.8408(3) 0.0840(13) Uani 0.726(8) 1 d . . P A 1
C1 C 0.7122(5) 0.1392(4) 0.7070(2) 0.0437(6) Uani 1 1 d . . . . .
F1 F 1.2795(13) 0.7628(8) 0.9530(4) 0.114(2) Uani 0.726(8) 1 d . . P A 1
F2 F 0.8685(9) 0.7119(8) 0.8954(4) 0.105(2) Uani 0.726(8) 1 d . . P A 1
B1 B 1.1066(13) 0.7569(10) 0.8690(4) 0.0371(15) Uani 0.726(8) 1 d . . P A 1
O1 O 0.3302(5) 0.3573(4) 0.8946(2) 0.0873(8) Uani 1 1 d DG . . . .
H1C H 0.290176 0.242526 0.923713 0.131 Uiso 1 1 d DG U . . .
H1D H 0.307015 0.430546 0.966449 0.131 Uiso 1 1 d DG U . . .
F3A F 1.138(6) 0.648(5) 0.798(2) 0.279(19) Uani 0.274(8) 1 d . . P A 2
F2A F 0.937(7) 0.795(5) 0.866(3) 0.33(2) Uani 0.274(8) 1 d . . P A 2
F4A F 1.277(4) 0.886(4) 0.9377(19) 0.215(14) Uani 0.274(8) 1 d . . P A 2
F1A F 1.017(5) 0.610(3) 0.9374(15) 0.181(8) Uani 0.274(8) 1 d . . P A 2
B1A B 1.072(10) 0.721(6) 0.871(6) 0.17(3) Uani 0.274(8) 1 d . . P A 2


_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
F3 B1 1.412(6) . ?
N4 C3 1.328(3) . ?
N4 C2 1.351(3) . ?
N6 H6 0.8700 . ?
N6 C3 1.358(3) . ?
N6 C1 1.353(3) . ?
N2 C2 1.352(3) . ?
N2 C1 1.327(3) . ?
N3 H3A 0.8700 . ?
N3 H3B 0.8700 . ?
N3 C2 1.320(3) . ?
N1 H1A 0.8700 . ?
N1 H1B 0.8700 . ?
N1 C1 1.315(3) . ?
N5 H5A 0.8700 . ?
N5 H5B 0.8700 . ?
N5 C3 1.316(3) . ?
F4 B1 1.393(7) . ?
F1 B1 1.333(8) . ?
F2 B1 1.367(8) . ?
O1 H1C 0.9495 . ?
O1 H1D 0.9539 . ?
F3A B1A 1.09(7) . ?
F2A B1A 1.10(5) . ?
F4A B1A 1.41(5) . ?
F1A B1A 1.23(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
C3 N4 C2 115.7(2) . . ?
C3 N6 H6 120.0 . . ?
C1 N6 H6 120.1 . . ?
C1 N6 C3 119.9(2) . . ?
C1 N2 C2 115.6(2) . . ?
H3A N3 H3B 120.0 . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C3 N5 H5A 120.0 . . ?
C3 N5 H5B 120.0 . . ?
N4 C3 N6 121.2(2) . . ?
N5 C3 N4 120.7(2) . . ?
N5 C3 N6 118.1(2) . . ?
N4 C2 N2 126.0(2) . . ?
N3 C2 N4 117.0(2) . . ?
N3 C2 N2 117.0(2) . . ?
N2 C1 N6 121.5(2) . . ?
N1 C1 N6 117.8(2) . . ?
N1 C1 N2 120.7(2) . . ?
F4 B1 F3 104.6(3) . . ?
F1 B1 F3 110.1(5) . . ?
F1 B1 F4 110.4(6) . . ?
F1 B1 F2 115.8(5) . . ?
F2 B1 F3 109.3(5) . . ?
F2 B1 F4 106.0(5) . . ?
H1C O1 H1D 91.2 . . ?
F3A B1A F2A 127(7) . . ?
F3A B1A F4A 108(5) . . ?
F3A B1A F1A 107(4) . . ?
F2A B1A F4A 97(4) . . ?
F2A B1A F1A 111(6) . . ?
F1A B1A F4A 104(5) . . ?

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
N6 H6 O1 0.87 1.88 2.727(3) 164.9 . yes
N5 H5B F3 0.87 2.16 2.830(4) 133.2 1_455 yes
O1 H1C F4 0.95 2.13 2.861(4) 133.2 1_445 yes
O1 H1D F2 0.95 2.24 2.864(4) 122.5 2_667 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
C3 N4 C2 N2 0.2(4) . . . . ?
C3 N4 C2 N3 179.1(2) . . . . ?
C3 N6 C1 N2 -1.0(4) . . . . ?
C3 N6 C1 N1 -179.7(2) . . . . ?
C2 N4 C3 N6 -0.8(4) . . . . ?
C2 N4 C3 N5 179.6(2) . . . . ?
C2 N2 C1 N6 0.3(4) . . . . ?
C2 N2 C1 N1 179.0(2) . . . . ?
C1 N6 C3 N4 1.3(4) . . . . ?
C1 N6 C3 N5 -179.2(2) . . . . ?
C1 N2 C2 N4 0.1(4) . . . . ?
C1 N2 C2 N3 -178.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
