# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2222290'
loop_
_audit_author_name
_audit_author_address
'Yaoguo Shen'
;Minjiang University
China
;
_audit_update_record             
;
2022-11-25 deposited with the CCDC.	2023-02-07 downloaded from the CCDC.
;
_audit_creation_date             2022-10-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Cl), H2 O, 2(C3 H7 N6)'
_chemical_formula_sum            'C6 H16 Cl2 N12 O'
_chemical_formula_weight         343.21
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   12.4484(12)
_cell_length_b                   17.6746(10)
_cell_length_c                   7.1271(6)
_cell_angle_alpha                90
_cell_angle_beta                 115.117(8)
_cell_angle_gamma                90
_cell_volume                     1419.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3778
_cell_measurement_theta_min      2.1320
_cell_measurement_theta_max      26.9650
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.480
_exptl_absorpt_correction_T_min  0.79671
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.606
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6197
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.358
_diffrn_reflns_theta_min         2.143
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1237
_reflns_number_total             1478
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.880
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.0054(10)
_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   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         1478
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.115
_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)+(0.0487P)²+2.4095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1200
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups, All O(H,H) groups
2. Restrained distances
 O1-H1B = O1-H1A
 0.85 with sigma of 0.02
3. Others
 Fixed Sof: H4A(0.5) H4B(0.5) H8A(0.5) H8B(0.5)
4.a Riding coordinates:
 O1(H1A,H1B), N1(H1), N2(H2A,H2B), N4(H4A,H4B), N5(H5), N6(H6A,H6B), N8(H8A,H8B)
;
_atom_sites_solution_hydrogens   difmap
_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
Cl Cl 0.70675(9) 0.500000 0.0772(2) 0.0566(4) Uani 1 2 d S T P . .
Cl2 Cl 0.94311(9) 0.500000 0.71408(14) 0.0445(3) Uani 1 2 d S T P . .
O1 O 0.6601(3) 0.500000 0.4871(6) 0.0708(10) Uani 1 2 d DS T P . .
H1A H 0.662899 0.500000 0.356786 0.085 Uiso 1 2 d DR U P . .
H1B H 0.737259 0.500000 0.598716 0.085 Uiso 1 2 d DR U P . .
N1 N 0.500000 0.15660(14) 0.500000 0.0323(6) Uani 1 2 d S T P . .
H1 H 0.500000 0.107938 0.500000 0.039 Uiso 1 2 d R U P . .
N2 N 0.31084(17) 0.15564(10) 0.4795(3) 0.0375(5) Uani 1 1 d . . . . .
H2A H 0.248303 0.178266 0.473554 0.045 Uiso 1 1 d R U . . .
H2B H 0.313233 0.107026 0.477764 0.045 Uiso 1 1 d R U . . .
N3 N 0.40130(15) 0.27025(9) 0.4938(3) 0.0247(4) Uani 1 1 d . . . . .
N4 N 0.500000 0.37982(14) 0.500000 0.0413(8) Uani 1 2 d S T P . .
H4A H 0.560720 0.404156 0.503800 0.050 Uiso 0.5 1 d R U P . .
H4B H 0.439280 0.404156 0.496200 0.050 Uiso 0.5 1 d R U P . .
C1 C 0.40287(18) 0.19547(11) 0.4909(3) 0.0247(5) Uani 1 1 d . . . . .
C2 C 0.500000 0.30525(16) 0.500000 0.0240(6) Uani 1 2 d S T P . .
N5 N 1.000000 0.65228(13) 0.000000 0.0308(6) Uani 1 2 d S T P . .
H5 H 1.000000 0.603618 0.000000 0.037 Uiso 1 2 d R U P . .
N6 N 0.81238(17) 0.65180(10) -0.0116(3) 0.0374(5) Uani 1 1 d . . . . .
H6A H 0.750530 0.674806 -0.015777 0.045 Uiso 1 1 d R U . . .
H6B H 0.814650 0.603166 -0.011107 0.045 Uiso 1 1 d R U . . .
N7 N 0.90112(15) 0.76594(9) -0.0068(3) 0.0243(4) Uani 1 1 d . . . . .
N8 N 1.000000 0.87553(14) 0.000000 0.0387(7) Uani 1 2 d S T P . .
H8A H 0.939190 0.899861 -0.004200 0.046 Uiso 0.5 1 d R U P . .
H8B H 1.060810 0.899861 0.004200 0.046 Uiso 0.5 1 d R U P . .
C3 C 0.90357(18) 0.69106(11) -0.0062(3) 0.0241(5) Uani 1 1 d . . . . .
C4 C 1.000000 0.80092(15) 0.000000 0.0234(6) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1A 0.9440 . ?
O1 H1B 0.9521 . ?
N1 H1 0.8600 . ?
N1 C1 1.368(2) 2_656 ?
N1 C1 1.368(2) . ?
N2 H2A 0.8603 . ?
N2 H2B 0.8599 . ?
N2 C1 1.317(3) . ?
N3 C1 1.322(3) . ?
N3 C2 1.359(2) . ?
N4 H4A 0.8601 . ?
N4 H4B 0.8601 . ?
N4 C2 1.318(4) . ?
N5 H5 0.8600 . ?
N5 C3 1.367(2) 2_755 ?
N5 C3 1.367(2) . ?
N6 H6A 0.8601 . ?
N6 H6B 0.8599 . ?
N6 C3 1.317(3) . ?
N7 C3 1.324(3) . ?
N7 C4 1.360(2) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N8 C4 1.319(4) . ?

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 112.1 . . ?
C1 N1 H1 120.1 2_656 . ?
C1 N1 H1 120.1 . . ?
C1 N1 C1 119.7(2) . 2_656 ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
C1 N3 C2 115.87(18) . . ?
H4A N4 H4B 120.0 . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
N2 C1 N1 117.55(19) . . ?
N2 C1 N3 121.13(19) . . ?
N3 C1 N1 121.32(19) . . ?
N3 C2 N3 125.9(2) . 2_656 ?
N4 C2 N3 117.07(12) . 2_656 ?
N4 C2 N3 117.07(12) . . ?
C3 N5 H5 120.1 . . ?
C3 N5 H5 120.1 2_755 . ?
C3 N5 C3 119.8(2) . 2_755 ?
H6A N6 H6B 120.0 . . ?
C3 N6 H6A 120.0 . . ?
C3 N6 H6B 120.0 . . ?
C3 N7 C4 115.80(18) . . ?
H8A N8 H8B 120.0 . . ?
C4 N8 H8A 120.0 . . ?
C4 N8 H8B 120.0 . . ?
N6 C3 N5 118.10(19) . . ?
N6 C3 N7 120.55(19) . . ?
N7 C3 N5 121.35(18) . . ?
N7 C4 N7 125.9(2) 2_755 . ?
N8 C4 N7 117.05(12) . . ?
N8 C4 N7 117.05(12) . 2_755 ?

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 N1 C1 N2 179.1(2) 2_656 . . . ?
C1 N1 C1 N3 -1.01(14) 2_656 . . . ?
C1 N3 C2 N3 -0.94(13) . . . 2_656 ?
C1 N3 C2 N4 179.06(13) . . . . ?
C2 N3 C1 N1 1.9(3) . . . . ?
C2 N3 C1 N2 -178.24(17) . . . . ?
C3 N5 C3 N6 -179.8(2) 2_755 . . . ?
C3 N5 C3 N7 0.15(14) 2_755 . . . ?
C3 N7 C4 N7 0.14(13) . . . 2_755 ?
C3 N7 C4 N8 -179.86(13) . . . . ?
C4 N7 C3 N5 -0.3(3) . . . . ?
C4 N7 C3 N6 179.71(17) . . . . ?

_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_kp_4_auto
_database_code_depnum_ccdc_archive 'CCDC 2222291'
loop_
_audit_author_name
_audit_author_address
'Yaoguo Shen'
;Minjiang University
China
;
_audit_update_record             
;
2022-11-25 deposited with the CCDC.	2023-02-07 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F, 0.5(H4 O2), C3 H7 N6'
_chemical_formula_sum            'C3 H9 F N6 O'
_chemical_formula_weight         164.16
_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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   10.6930(9)
_cell_length_b                   16.5835(16)
_cell_length_c                   3.7880(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.235(9)
_cell_angle_gamma                90
_cell_volume                     666.37(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1069
_cell_measurement_theta_min      2.2600
_cell_measurement_theta_max      25.8220
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.993
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_min  0.26660
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            2314
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.753
_diffrn_reflns_theta_min         2.279
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  
'XtaLAB Pro II AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                507
_reflns_number_total             717
_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    ?
_computing_publication_material  ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     55
_refine_ls_number_reflns         717
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0563
_refine_ls_restrained_S_all      1.131
_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)+(0.0822P)²+0.6711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1561
_refine_ls_wR_factor_ref         0.1737
_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. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H3A(0.5) H3B(0.5)
3.a Riding coordinates:
 O1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1)
3.c X=CH2 refined with riding coordinates:
 N3(H3A,H3B), N4(H4B,H4A)
;
_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
F1 F 0.6330(3) 0.500000 0.4930(7) 0.0552(8) Uani 1 2 d S T P . .
O1 O 0.3098(2) 1.000000 0.2131(7) 0.0336(7) Uani 1 2 d S T P . .
H1A H 0.263389 1.012860 0.370420 0.050 Uiso 0.5 1 d R U P . .
H1B H 0.285229 1.007150 -0.006870 0.050 Uiso 0.5 1 d R U P . .
N1 N 0.500000 0.64809(18) 0.500000 0.0319(8) Uani 1 2 d S T P . .
H1 H 0.499999 0.596234 0.499998 0.038 Uiso 1 2 calc R U P . .
N2 N 0.59994(18) 0.76911(12) 0.6870(6) 0.0307(6) Uani 1 1 d . . . . .
N3 N 0.500000 0.88590(19) 0.500000 0.0433(9) Uani 1 2 d S T P . .
H3A H 0.438250 0.911830 0.384479 0.052 Uiso 0.5 1 calc R U P . .
H3B H 0.561750 0.911830 0.615521 0.052 Uiso 0.5 1 calc R U P . .
N4 N 0.6905(2) 0.64739(14) 0.8532(6) 0.0382(7) Uani 1 1 d . . . . .
H4B H 0.753013 0.671777 0.972990 0.046 Uiso 1 1 calc R U . . .
H4A H 0.688480 0.595561 0.846893 0.046 Uiso 1 1 calc R U . . .
C1 C 0.5984(2) 0.68921(15) 0.6802(6) 0.0274(6) Uani 1 1 d . . . . .
C2 C 0.500000 0.8063(2) 0.500000 0.0298(8) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1A 0.8493 . ?
O1 H1A 0.8493 6_575 ?
O1 H1B 0.8501 . ?
O1 H1B 0.8501 6_575 ?
N1 H1 0.8600 . ?
N1 C1 1.363(3) 2_656 ?
N1 C1 1.363(3) . ?
N2 C1 1.325(3) . ?
N2 C2 1.354(3) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N3 C2 1.320(5) . ?
N4 H4B 0.8600 . ?
N4 H4A 0.8600 . ?
N4 C1 1.311(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 H1A 29.1 . 6_575 ?
H1A O1 H1B 125.9 . 6_575 ?
H1A O1 H1B 121.1 . . ?
H1A O1 H1B 121.1 6_575 6_575 ?
H1B O1 H1A 125.9 . 6_575 ?
H1B O1 H1B 16.0 . 6_575 ?
C1 N1 H1 120.0 . . ?
C1 N1 H1 120.0 2_656 . ?
C1 N1 C1 119.9(3) 2_656 . ?
C1 N2 C2 116.0(2) . . ?
H3A N3 H3B 120.0 . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
H4B N4 H4A 120.0 . . ?
C1 N4 H4B 120.0 . . ?
C1 N4 H4A 120.0 . . ?
N2 C1 N1 121.1(2) . . ?
N4 C1 N1 118.0(2) . . ?
N4 C1 N2 120.8(2) . . ?
N2 C2 N2 125.8(3) 2_656 . ?
N3 C2 N2 117.09(16) . 2_656 ?
N3 C2 N2 117.09(16) . . ?

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
O1 H1A F1 0.85 1.54 2.281(4) 144.0 3_455 yes
N1 H1 F1 0.86 2.14 2.840(3) 138.2 . yes
N1 H1 F1 0.86 2.14 2.840(3) 138.2 2_656 yes
N3 H3A O1 0.86 2.05 2.888(3) 163.0 . yes
N3 H3B O1 0.86 2.05 2.888(3) 163.0 2_656 yes
N4 H4A F1 0.86 2.11 2.829(3) 140.5 . 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
C1 N1 C1 N2 0.65(16) 2_656 . . . ?
C1 N1 C1 N4 179.3(2) 2_656 . . . ?
C1 N2 C2 N2 0.61(15) . . . 2_656 ?
C1 N2 C2 N3 -179.39(15) . . . . ?
C2 N2 C1 N1 -1.2(3) . . . . ?
C2 N2 C1 N4 -179.84(19) . . . . ?

