# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_L-Nb
_database_code_depnum_ccdc_archive 'CCDC 2084347'
loop_
_audit_author_name
_audit_author_address
'Kang Min Ok'
;Sogang University
South Korea
;
_audit_update_record             
;
2021-05-18 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C6 H11 N3 O2, F5 Nb O'
_chemical_formula_sum            'C6 H11 F5 N3 Nb O3'
_chemical_formula_weight         361.09
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.4379(3)
_cell_length_b                   8.6707(4)
_cell_length_c                   11.7924(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.2698(14)
_cell_angle_gamma                90
_cell_volume                     548.76(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9773
_cell_measurement_theta_min      3.8
_cell_measurement_theta_max      28.34
_cell_measurement_wavelength     0.71076

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.252
_exptl_crystal_size_min          0.168
_exptl_crystal_density_diffrn    2.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2016/2 - Bruker AXS area detector scaling and absorption correcti
;
_exptl_absorpt_correction_T_min  0.6538
_exptl_absorpt_correction_T_max  0.7457

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'PHOTON II CPAD detector'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_ub_11      -0.051208
_diffrn_orient_matrix_ub_12      -0.067964
_diffrn_orient_matrix_ub_13      0.06062
_diffrn_orient_matrix_ub_21      0.161015
_diffrn_orient_matrix_ub_22      -0.057429
_diffrn_orient_matrix_ub_23      0.005722
_diffrn_orient_matrix_ub_31      0.078549
_diffrn_orient_matrix_ub_32      0.073376
_diffrn_orient_matrix_ub_33      0.060623
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_number            26495
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.797
_diffrn_reflns_theta_max         28.353
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_coverage         0.877
_reflns_number_total             2739
_reflns_number_gt                2713
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 software'
_computing_cell_refinement       'SAINT V8.38A integration software'
_computing_data_reduction        'Bruker APEX3 software'
_computing_structure_solution    'SHELXS-2013/2 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0159P)²+0.3208P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.114(4)
_refine_ls_number_reflns         2739
_refine_ls_number_parameters     165
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0159
_refine_ls_R_factor_gt           0.0157
_refine_ls_wR_factor_ref         0.0399
_refine_ls_wR_factor_gt          0.0398
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1252 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(7)
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.053

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'
Nb Nb -2.0727 0.6215 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Nb1 Nb 0.17296(4) 0.73192(3) 0.74028(2) 0.02158(9) Uani 1 1 d . . . . .
C1 C 0.8488(5) 0.1985(3) 0.8983(2) 0.0191(6) Uani 1 1 d . . . . .
H1 H 1.0025 0.217391 0.952385 0.023 Uiso 1 1 calc R U . . .
C2 C 0.6571(5) 0.3181(3) 0.9181(2) 0.0210(5) Uani 1 1 d . . . . .
C3 C 0.9055(5) 0.2133(5) 0.7750(2) 0.0242(6) Uani 1 1 d . . . . .
H3A H 0.989594 0.310571 0.767736 0.029 Uiso 1 1 calc R U . . .
H3B H 1.018034 0.131085 0.761206 0.029 Uiso 1 1 calc R U . . .
C4 C 0.6761(5) 0.2058(3) 0.6850(2) 0.0239(7) Uani 1 1 d . . . . .
C5 C 0.5060(6) 0.3135(4) 0.6458(3) 0.0327(7) Uani 1 1 d . . . . .
H5 H 0.509231 0.416718 0.667353 0.039 Uiso 1 1 calc R U . . .
C6 C 0.3870(7) 0.0971(4) 0.5588(3) 0.0367(7) Uani 1 1 d . . . . .
H6 H 0.29684 0.024406 0.511146 0.044 Uiso 1 1 calc R U . . .
N1 N 0.7501(6) 0.0440(3) 0.9228(2) 0.0228(6) Uani 1 1 d . . . . .
H1A H 0.741056 0.036828 0.997279 0.034 Uiso 1 1 calc R U . . .
H1B H 0.851314 -0.028868 0.903793 0.034 Uiso 1 1 calc R U . . .
H1C H 0.598914 0.031715 0.881885 0.034 Uiso 1 1 calc R U . . .
N2 N 0.5971(5) 0.0717(3) 0.6288(2) 0.0318(6) Uani 1 1 d . . . . .
H2N H 0.673141 -0.015483 0.637889 0.038 Uiso 1 1 calc R U . . .
N3 N 0.3262(4) 0.2428(6) 0.5677(2) 0.0356(6) Uani 1 1 d . . . . .
H3N H 0.195532 0.286641 0.530752 0.043 Uiso 1 1 calc R U . . .
O1 O 0.7488(5) 0.4590(3) 0.9136(2) 0.0316(6) Uani 1 1 d . . . . .
H1O H 0.642869 0.52235 0.924122 0.047 Uiso 1 1 calc R U . . .
O2 O 0.4468(4) 0.2863(3) 0.9297(2) 0.0303(5) Uani 1 1 d . . . . .
O3 O 0.3427(4) 0.6164(3) 0.85183(19) 0.0321(5) Uani 1 1 d . . . . .
F1 F 0.4144(3) 0.7277(5) 0.64071(16) 0.0512(5) Uani 1 1 d . . . . .
F2 F -0.0040(5) 0.5630(2) 0.6613(2) 0.0439(6) Uani 1 1 d . . . . .
F3 F -0.0915(4) 0.7785(2) 0.82803(19) 0.0407(5) Uani 1 1 d . . . . .
F4 F 0.3126(4) 0.9288(2) 0.80227(19) 0.0379(5) Uani 1 1 d . . . . .
F5 F -0.0312(4) 0.8667(2) 0.61415(19) 0.0351(5) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Nb1 O3 1.787(2) . ?
Nb1 F1 1.8973(16) . ?
Nb1 F2 1.911(2) . ?
Nb1 F3 1.9447(19) . ?
Nb1 F4 1.9613(19) . ?
Nb1 F5 2.0687(19) . ?
C1 N1 1.488(4) . ?
C1 C2 1.516(4) . ?
C1 C3 1.540(3) . ?
C1 H1 0.98 . ?
C2 O2 1.205(3) . ?
C2 O1 1.324(4) . ?
C3 C4 1.503(4) . ?
C3 H3A 0.97 . ?
C3 H3B 0.97 . ?
C4 C5 1.343(4) . ?
C4 N2 1.373(4) . ?
C5 N3 1.374(5) . ?
C5 H5 0.93 . ?
C6 N3 1.314(6) . ?
C6 N2 1.316(4) . ?
C6 H6 0.93 . ?
N1 H1A 0.89 . ?
N1 H1B 0.89 . ?
N1 H1C 0.89 . ?
N2 H2N 0.86 . ?
N3 H3N 0.86 . ?
O1 H1O 0.82 . ?

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 Nb1 F1 96.78(12) . . ?
O3 Nb1 F2 95.10(11) . . ?
F1 Nb1 F2 91.60(14) . . ?
O3 Nb1 F3 93.63(11) . . ?
F1 Nb1 F3 167.95(14) . . ?
F2 Nb1 F3 93.51(10) . . ?
O3 Nb1 F4 95.20(11) . . ?
F1 Nb1 F4 89.00(14) . . ?
F2 Nb1 F4 169.53(10) . . ?
F3 Nb1 F4 84.02(10) . . ?
O3 Nb1 F5 178.35(11) . . ?
F1 Nb1 F5 84.87(11) . . ?
F2 Nb1 F5 84.99(10) . . ?
F3 Nb1 F5 84.71(9) . . ?
F4 Nb1 F5 84.65(8) . . ?
N1 C1 C2 107.9(2) . . ?
N1 C1 C3 113.0(2) . . ?
C2 C1 C3 109.6(2) . . ?
N1 C1 H1 108.7 . . ?
C2 C1 H1 108.7 . . ?
C3 C1 H1 108.7 . . ?
O2 C2 O1 125.9(3) . . ?
O2 C2 C1 123.3(2) . . ?
O1 C2 C1 110.6(2) . . ?
C4 C3 C1 113.2(2) . . ?
C4 C3 H3A 108.9 . . ?
C1 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C1 C3 H3B 108.9 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 N2 106.1(3) . . ?
C5 C4 C3 131.4(3) . . ?
N2 C4 C3 122.5(3) . . ?
C4 C5 N3 107.3(3) . . ?
C4 C5 H5 126.4 . . ?
N3 C5 H5 126.4 . . ?
N3 C6 N2 108.4(3) . . ?
N3 C6 H6 125.8 . . ?
N2 C6 H6 125.8 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C6 N2 C4 109.5(3) . . ?
C6 N2 H2N 125.3 . . ?
C4 N2 H2N 125.3 . . ?
C6 N3 C5 108.7(3) . . ?
C6 N3 H3N 125.6 . . ?
C5 N3 H3N 125.6 . . ?
C2 O1 H1O 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
N1 C1 C2 O2 -12.7(4) . . . . ?
C3 C1 C2 O2 110.8(3) . . . . ?
N1 C1 C2 O1 171.1(2) . . . . ?
C3 C1 C2 O1 -65.4(3) . . . . ?
N1 C1 C3 C4 66.3(3) . . . . ?
C2 C1 C3 C4 -54.1(3) . . . . ?
C1 C3 C4 C5 81.0(4) . . . . ?
C1 C3 C4 N2 -95.9(3) . . . . ?
N2 C4 C5 N3 0.6(3) . . . . ?
C3 C4 C5 N3 -176.6(3) . . . . ?
N3 C6 N2 C4 -0.1(4) . . . . ?
C5 C4 N2 C6 -0.3(4) . . . . ?
C3 C4 N2 C6 177.3(3) . . . . ?
N2 C6 N3 C5 0.6(4) . . . . ?
C4 C5 N3 C6 -0.8(4) . . . . ?

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
N1 H1A O3 0.89 2.03 2.854(4) 154 2_647 yes
N1 H1B F3 0.89 1.94 2.756(3) 151.3 1_645 yes
N1 H1C F4 0.89 1.91 2.755(3) 159 1_545 yes
N2 H2N F5 0.86 1.96 2.718(4) 145.9 1_645 yes
N3 H3N F5 0.86 1.93 2.687(3) 146.7 2_546 yes
O1 H1O O3 0.82 1.9 2.599(4) 142.5 . yes
####################################################################### 
# 
# 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_D-Nb
_database_code_depnum_ccdc_archive 'CCDC 2084348'
loop_
_audit_author_name
_audit_author_address
'Kang Min Ok'
;Sogang University
South Korea
;
_audit_update_record             
;
2021-05-18 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;

_audit_creation_date             2021-04-14T21:27:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C6 H11 N3 O2, F5 Nb O'
_chemical_formula_sum            'C6 H11 F5 N3 Nb O3'
_chemical_formula_weight         361.09
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.4387(3)
_cell_length_b                   8.6700(4)
_cell_length_c                   11.7930(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.276(2)
_cell_angle_gamma                90
_cell_volume                     548.81(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9037
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      28.3
_cell_measurement_wavelength     0.71076

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.119
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.079
_exptl_crystal_density_diffrn    2.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2016/2 - Bruker AXS area detector scaling and absorption correcti
;
_exptl_absorpt_correction_T_min  0.6538
_exptl_absorpt_correction_T_max  0.7457
_shelx_estimated_absorpt_T_min   0.873
_shelx_estimated_absorpt_T_max   0.913

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'PHOTON II CPAD detector'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_ub_11      -0.028866
_diffrn_orient_matrix_ub_12      -0.00548
_diffrn_orient_matrix_ub_13      0.081529
_diffrn_orient_matrix_ub_21      0.038081
_diffrn_orient_matrix_ub_22      -0.112892
_diffrn_orient_matrix_ub_23      0.001557
_diffrn_orient_matrix_ub_31      0.180073
_diffrn_orient_matrix_ub_32      0.022999
_diffrn_orient_matrix_ub_33      0.027069
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_number            30716
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         28.351
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_coverage         0.876
_reflns_number_total             2743
_reflns_number_gt                2625
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 software'
_computing_cell_refinement       'SAINT V8.38A integration software'
_computing_data_reduction        'Bruker APEX3 software'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0068P)²+0.5851P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0069(9)
_refine_ls_number_reflns         2743
_refine_ls_number_parameters     165
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.046
_refine_ls_wR_factor_gt          0.0449
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1161 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(9)
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.46
_refine_diff_density_rms         0.071

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'
Nb Nb -2.0727 0.6215 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Nb1 Nb 0.82723(6) 0.26804(5) 0.25985(3) 0.02124(10) Uani 1 1 d . . . . .
C1 C 0.1515(7) 0.8013(4) 0.1017(3) 0.0197(9) Uani 1 1 d . . . . .
H1 H -0.002265 0.78234 0.04763 0.024 Uiso 1 1 calc R U . . .
C2 C 0.3432(7) 0.6826(5) 0.0817(3) 0.0203(8) Uani 1 1 d . . . . .
C3 C 0.0949(7) 0.7877(7) 0.2250(3) 0.0227(10) Uani 1 1 d . . . . .
H3A H -0.015846 0.870997 0.238623 0.027 Uiso 1 1 calc R U . . .
H3B H 0.008642 0.691253 0.232396 0.027 Uiso 1 1 calc R U . . .
C4 C 0.3236(7) 0.7936(6) 0.3150(3) 0.0243(11) Uani 1 1 d . . . . .
C5 C 0.4938(9) 0.6866(6) 0.3541(4) 0.0318(10) Uani 1 1 d . . . . .
H5 H 0.491219 0.583477 0.332298 0.038 Uiso 1 1 calc R U . . .
C6 C 0.6140(9) 0.9030(6) 0.4412(4) 0.0359(11) Uani 1 1 d . . . . .
H6 H 0.704886 0.97569 0.488547 0.043 Uiso 1 1 calc R U . . .
N1 N 0.2505(9) 0.9559(5) 0.0774(4) 0.0226(10) Uani 1 1 d . . . . .
H1A H 0.260274 0.963053 0.003003 0.034 Uiso 1 1 calc R U . . .
H1B H 0.40132 0.968213 0.118619 0.034 Uiso 1 1 calc R U . . .
H1C H 0.148959 1.028754 0.096158 0.034 Uiso 1 1 calc R U . . .
N2 N 0.4029(8) 0.9284(5) 0.3710(3) 0.0316(9) Uani 1 1 d . . . . .
H2N H 0.326797 1.01551 0.361798 0.038 Uiso 1 1 calc R U . . .
N3 N 0.6730(6) 0.7574(8) 0.4323(3) 0.0352(9) Uani 1 1 d . . . . .
H3N H 0.80308 0.713198 0.46947 0.042 Uiso 1 1 calc R U . . .
O1 O 0.2507(8) 0.5409(4) 0.0865(3) 0.0307(9) Uani 1 1 d . . . . .
H1O H 0.356605 0.477482 0.075962 0.046 Uiso 1 1 calc R U . . .
O2 O 0.5532(5) 0.7138(3) 0.0703(3) 0.0293(7) Uani 1 1 d . . . . .
O3 O 0.6574(6) 0.3835(4) 0.1483(3) 0.0314(7) Uani 1 1 d . . . . .
F1 F 0.5862(4) 0.2720(7) 0.3591(2) 0.0508(7) Uani 1 1 d . . . . .
F2 F 1.0033(7) 0.4372(3) 0.3386(3) 0.0432(9) Uani 1 1 d . . . . .
F3 F 1.0914(5) 0.2216(3) 0.1723(3) 0.0399(8) Uani 1 1 d . . . . .
F4 F 0.6874(5) 0.0716(3) 0.1979(3) 0.0376(7) Uani 1 1 d . . . . .
F5 F 1.0310(6) 0.1336(3) 0.3859(3) 0.0346(7) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Nb1 O3 1.787(3) . ?
Nb1 F1 1.893(2) . ?
Nb1 F2 1.909(3) . ?
Nb1 F3 1.942(3) . ?
Nb1 F4 1.958(3) . ?
Nb1 F5 2.065(3) . ?
C1 N1 1.489(5) . ?
C1 C2 1.510(5) . ?
C1 C3 1.539(5) . ?
C1 H1 0.98 . ?
C2 O2 1.203(5) . ?
C2 O1 1.332(5) . ?
C3 C4 1.500(5) . ?
C3 H3A 0.97 . ?
C3 H3B 0.97 . ?
C4 C5 1.339(6) . ?
C4 N2 1.377(6) . ?
C5 N3 1.374(6) . ?
C5 H5 0.93 . ?
C6 N3 1.311(8) . ?
C6 N2 1.321(6) . ?
C6 H6 0.93 . ?
N1 H1A 0.89 . ?
N1 H1B 0.89 . ?
N1 H1C 0.89 . ?
N2 H2N 0.86 . ?
N3 H3N 0.86 . ?
O1 H1O 0.82 . ?

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 Nb1 F1 96.76(16) . . ?
O3 Nb1 F2 95.00(15) . . ?
F1 Nb1 F2 91.60(19) . . ?
O3 Nb1 F3 93.65(14) . . ?
F1 Nb1 F3 167.94(19) . . ?
F2 Nb1 F3 93.55(14) . . ?
O3 Nb1 F4 95.10(15) . . ?
F1 Nb1 F4 88.90(19) . . ?
F2 Nb1 F4 169.75(13) . . ?
F3 Nb1 F4 84.10(13) . . ?
O3 Nb1 F5 178.40(16) . . ?
F1 Nb1 F5 84.83(15) . . ?
F2 Nb1 F5 85.09(14) . . ?
F3 Nb1 F5 84.75(13) . . ?
F4 Nb1 F5 84.76(11) . . ?
N1 C1 C2 107.7(3) . . ?
N1 C1 C3 112.6(4) . . ?
C2 C1 C3 110.1(3) . . ?
N1 C1 H1 108.8 . . ?
C2 C1 H1 108.8 . . ?
C3 C1 H1 108.8 . . ?
O2 C2 O1 125.8(4) . . ?
O2 C2 C1 123.8(4) . . ?
O1 C2 C1 110.3(4) . . ?
C4 C3 C1 113.4(3) . . ?
C4 C3 H3A 108.9 . . ?
C1 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C1 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 N2 106.1(4) . . ?
C5 C4 C3 132.0(5) . . ?
N2 C4 C3 121.9(4) . . ?
C4 C5 N3 107.4(5) . . ?
C4 C5 H5 126.3 . . ?
N3 C5 H5 126.3 . . ?
N3 C6 N2 108.0(4) . . ?
N3 C6 H6 126 . . ?
N2 C6 H6 126 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C6 N2 C4 109.4(4) . . ?
C6 N2 H2N 125.3 . . ?
C4 N2 H2N 125.3 . . ?
C6 N3 C5 109.1(4) . . ?
C6 N3 H3N 125.4 . . ?
C5 N3 H3N 125.4 . . ?
C2 O1 H1O 109.5 . . ?

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
N1 H1A O3 0.89 2.03 2.857(5) 154.2 2_655 yes
N1 H1B F4 0.89 1.91 2.754(5) 158.8 1_565 yes
N1 H1C F3 0.89 1.95 2.760(5) 151.2 1_465 yes
N2 H2N F5 0.86 1.97 2.721(5) 145.9 1_465 yes
N3 H3N F5 0.86 1.92 2.689(5) 147.3 2_756 yes
O1 H1O O3 0.82 1.9 2.601(5) 142.5 . yes

####################################################################### 
# 
# 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_D-Ta
_database_code_depnum_ccdc_archive 'CCDC 2084350'
loop_
_audit_author_name
_audit_author_address
'Kang Min Ok'
;Sogang University
South Korea
;
_audit_update_record             
;
2021-05-18 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C6 H11 N3 O2, F7 Ta'
_chemical_formula_sum            'C6 H11 F7 N3 O2 Ta'
_chemical_formula_weight         471.13
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.8004(13)
_cell_length_b                   8.2153(13)
_cell_length_c                   9.2627(14)
_cell_angle_alpha                90
_cell_angle_beta                 109.890(4)
_cell_angle_gamma                90
_cell_volume                     558.17(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9994
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      28.3
_cell_measurement_wavelength     0.71076

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.065
_exptl_crystal_density_diffrn    2.803
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    9.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2016/2 - Bruker AXS area detector scaling and absorption correcti
;
_exptl_absorpt_correction_T_min  0.505
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.281
_shelx_estimated_absorpt_T_max   0.564

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector                 'PHOTON II CPAD detector'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_ub_11      0.016914
_diffrn_orient_matrix_ub_12      -0.043465
_diffrn_orient_matrix_ub_13      -0.095103
_diffrn_orient_matrix_ub_21      0.121398
_diffrn_orient_matrix_ub_22      -0.045232
_diffrn_orient_matrix_ub_23      0.063138
_diffrn_orient_matrix_ub_31      -0.059687
_diffrn_orient_matrix_ub_32      -0.104315
_diffrn_orient_matrix_ub_33      0.01225
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_number            9523
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.777
_diffrn_reflns_theta_max         28.294
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_coverage         0.868
_reflns_number_total             2763
_reflns_number_gt                2749
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 software'
_computing_cell_refinement       'SAINT V8.40A integration software'
_computing_data_reduction        'Bruker APEX3 software'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0099P)²+0.6097P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0091(5)
_refine_ls_number_reflns         2763
_refine_ls_number_parameters     174
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0134
_refine_ls_R_factor_gt           0.0133
_refine_ls_wR_factor_ref         0.0313
_refine_ls_wR_factor_gt          0.0312
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1256 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(6)
_refine_diff_density_max         0.5
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.096

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'
Ta Ta -0.7052 6.5227 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Ta1 Ta 0.68907(2) 0.48523(5) 0.94806(2) 0.00689(6) Uani 1 1 d . . . . .
C1 C 0.2240(5) 0.4593(5) 0.2777(5) 0.0082(11) Uani 1 1 d . . . . .
H1 H 0.125989 0.374691 0.250886 0.01 Uiso 1 1 calc R U . . .
C2 C 0.3837(6) 0.4047(5) 0.4159(5) 0.0092(8) Uani 1 1 d . . . . .
C3 C 0.1494(6) 0.6226(5) 0.3182(5) 0.0107(8) Uani 1 1 d . . . . .
H3A H 0.245609 0.706598 0.337418 0.013 Uiso 1 1 calc R U . . .
H3B H 0.044775 0.658227 0.228529 0.013 Uiso 1 1 calc R U . . .
C4 C 0.0901(6) 0.6129(5) 0.4538(5) 0.0100(8) Uani 1 1 d . . . . .
C5 C 0.1835(6) 0.6509(6) 0.6030(5) 0.0126(8) Uani 1 1 d . . . . .
H5 H 0.302578 0.695883 0.642292 0.015 Uiso 1 1 calc R U . . .
C6 C -0.0840(6) 0.5530(6) 0.5924(5) 0.0118(8) Uani 1 1 d . . . . .
H6 H -0.184193 0.518467 0.620952 0.014 Uiso 1 1 calc R U . . .
N1 N 0.2908(4) 0.4837(9) 0.1469(3) 0.0106(5) Uani 1 1 d . . . . .
H1A H 0.266194 0.587384 0.111144 0.016 Uiso 1 1 calc R U . . .
H1B H 0.23393 0.412361 0.070461 0.016 Uiso 1 1 calc R U . . .
H1C H 0.413311 0.466434 0.178948 0.016 Uiso 1 1 calc R U . . .
N2 N -0.0756(5) 0.5511(5) 0.4511(4) 0.0109(7) Uani 1 1 d . . . . .
H2N H -0.162468 0.515827 0.368635 0.013 Uiso 1 1 calc R U . . .
N3 N 0.0732(5) 0.6119(5) 0.6862(4) 0.0123(7) Uani 1 1 d . . . . .
H3N H 0.102077 0.624126 0.786003 0.015 Uiso 1 1 calc R U . . .
O1 O 0.3296(4) 0.3320(4) 0.5186(4) 0.0119(6) Uani 1 1 d . . . . .
H1O H 0.420898 0.302945 0.593053 0.018 Uiso 1 1 calc R U . . .
O2 O 0.5411(4) 0.4341(4) 0.4281(4) 0.0141(7) Uani 1 1 d . . . . .
F1 F 0.5811(5) 0.3223(4) 0.7843(4) 0.0150(7) Uani 1 1 d . . . . .
F2 F 0.4369(3) 0.5187(3) 0.9193(3) 0.0146(7) Uani 1 1 d . . . . .
F3 F 0.7558(6) 0.7037(5) 1.0311(5) 0.0172(8) Uani 1 1 d . . . . .
F4 F 0.9268(3) 0.5027(7) 0.9246(3) 0.0157(8) Uani 1 1 d . . . . .
F5 F 0.8071(5) 0.2766(6) 1.0285(4) 0.0146(8) Uani 1 1 d . . . . .
F6 F 0.6914(3) 0.4698(8) 1.1614(3) 0.0162(7) Uani 1 1 d . . . . .
F7 F 0.6274(5) 0.6160(4) 0.7606(4) 0.0165(7) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Ta1 F2 1.913(3) . ?
Ta1 F4 1.944(3) . ?
Ta1 F3 1.952(4) . ?
Ta1 F7 1.958(3) . ?
Ta1 F5 1.968(5) . ?
Ta1 F6 1.974(2) . ?
Ta1 F1 1.983(3) . ?
C1 N1 1.487(5) . ?
C1 C2 1.519(6) . ?
C1 C3 1.558(6) . ?
C1 H1 1 . ?
C2 O2 1.218(5) . ?
C2 O1 1.309(5) . ?
C3 C4 1.481(6) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.362(6) . ?
C4 N2 1.381(6) . ?
C5 N3 1.373(6) . ?
C5 H5 0.95 . ?
C6 N3 1.329(6) . ?
C6 N2 1.332(6) . ?
C6 H6 0.95 . ?
N1 H1A 0.91 . ?
N1 H1B 0.91 . ?
N1 H1C 0.91 . ?
N2 H2N 0.88 . ?
N3 H3N 0.88 . ?
O1 H1O 0.84 . ?

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
F2 Ta1 F4 161.53(15) . . ?
F2 Ta1 F3 92.68(15) . . ?
F4 Ta1 F3 80.7(2) . . ?
F2 Ta1 F7 82.36(12) . . ?
F4 Ta1 F7 79.41(15) . . ?
F3 Ta1 F7 78.29(16) . . ?
F2 Ta1 F5 120.27(13) . . ?
F4 Ta1 F5 76.45(19) . . ?
F3 Ta1 F5 128.60(13) . . ?
F7 Ta1 F5 139.09(15) . . ?
F2 Ta1 F6 78.90(11) . . ?
F4 Ta1 F6 115.60(11) . . ?
F3 Ta1 F6 75.8(2) . . ?
F7 Ta1 F6 147.0(2) . . ?
F5 Ta1 F6 73.8(2) . . ?
F2 Ta1 F1 80.87(12) . . ?
F4 Ta1 F1 97.91(17) . . ?
F3 Ta1 F1 155.34(15) . . ?
F7 Ta1 F1 77.27(13) . . ?
F5 Ta1 F1 73.97(15) . . ?
F6 Ta1 F1 125.41(19) . . ?
N1 C1 C2 108.2(3) . . ?
N1 C1 C3 110.1(4) . . ?
C2 C1 C3 108.5(3) . . ?
N1 C1 H1 110 . . ?
C2 C1 H1 110 . . ?
C3 C1 H1 110 . . ?
O2 C2 O1 125.9(4) . . ?
O2 C2 C1 122.1(4) . . ?
O1 C2 C1 111.9(4) . . ?
C4 C3 C1 114.1(4) . . ?
C4 C3 H3A 108.7 . . ?
C1 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C1 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C5 C4 N2 106.0(4) . . ?
C5 C4 C3 129.5(4) . . ?
N2 C4 C3 124.4(4) . . ?
C4 C5 N3 107.2(4) . . ?
C4 C5 H5 126.4 . . ?
N3 C5 H5 126.4 . . ?
N3 C6 N2 107.7(4) . . ?
N3 C6 H6 126.2 . . ?
N2 C6 H6 126.2 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C6 N2 C4 109.7(4) . . ?
C6 N2 H2N 125.2 . . ?
C4 N2 H2N 125.2 . . ?
C6 N3 C5 109.4(4) . . ?
C6 N3 H3N 125.3 . . ?
C5 N3 H3N 125.3 . . ?
C2 O1 H1O 109.5 . . ?

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
N1 H1A F1 0.91 2.3 2.951(8) 128.1 2_656 yes
N1 H1A F5 0.91 1.98 2.857(8) 162.1 2_656 yes
N1 H1B F3 0.91 1.97 2.781(7) 147.6 2_646 yes
N1 H1B F4 0.91 2.43 2.889(4) 111.3 1_454 yes
N1 H1C O2 0.91 2.2 2.703(4) 114.4 . yes
N1 H1C F6 0.91 2.23 3.084(4) 156 1_554 yes
N2 H2N F6 0.88 1.91 2.763(5) 163.5 1_454 yes
N3 H3N F4 0.88 2.39 2.950(5) 121.9 1_455 yes
N3 H3N F5 0.88 2.05 2.830(6) 147.5 2_657 yes
O1 H1O F1 0.84 1.79 2.574(5) 153.7 . yes

####################################################################### 
# 
# 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_L-Ta
_database_code_depnum_ccdc_archive 'CCDC 2084349'
loop_
_audit_author_name
_audit_author_address
'Kang Min Ok'
;Sogang University
South Korea
;
_audit_update_record             
;
2021-05-18 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;

_audit_creation_date             2021-05-17T21:34:18-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C6 H11 N3 O2, F7 Ta'
_chemical_formula_sum            'C6 H11 F7 N3 O2 Ta'
_chemical_formula_weight         471.13
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.8041(7)
_cell_length_b                   8.2249(8)
_cell_length_c                   9.2616(9)
_cell_angle_alpha                90
_cell_angle_beta                 109.939(2)
_cell_angle_gamma                90
_cell_volume                     558.85(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9904
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      28.44
_cell_measurement_wavelength     0.71076

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.105
_exptl_crystal_density_diffrn    2.8
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    9.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2016/2 - Bruker AXS area detector scaling and absorption correcti
;
_exptl_absorpt_correction_T_min  0.579
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.113
_shelx_estimated_absorpt_T_max   0.422

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'PHOTON II CPAD detector'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_ub_11      -0.049497
_diffrn_orient_matrix_ub_12      -0.112646
_diffrn_orient_matrix_ub_13      0.024788
_diffrn_orient_matrix_ub_21      0.122713
_diffrn_orient_matrix_ub_22      -0.03914
_diffrn_orient_matrix_ub_23      -0.003603
_diffrn_orient_matrix_ub_31      -0.032742
_diffrn_orient_matrix_ub_32      0.023685
_diffrn_orient_matrix_ub_33      0.112094
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_number            21177
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.407
_diffrn_reflns_theta_max         28.439
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.99
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.983
_reflns_Friedel_coverage         0.86
_reflns_number_total             2801
_reflns_number_gt                2798
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 software'
_computing_cell_refinement       'SAINT V8.38A integration software'
_computing_data_reduction        'Bruker APEX3 software'
_computing_structure_solution    'SHELXS-2013/2 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0039P)²+0.5112P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0296(9)
_refine_ls_number_reflns         2801
_refine_ls_number_parameters     175
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0129
_refine_ls_R_factor_gt           0.0129
_refine_ls_wR_factor_ref         0.0332
_refine_ls_wR_factor_gt          0.0332
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.048(11)
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.872
_refine_diff_density_rms         0.121

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'
Ta Ta -0.7052 6.5227 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Ta1 Ta 0.31089(2) 0.51475(7) 0.05172(2) 0.00638(7) Uani 1 1 d . . . . .
C1 C 0.7763(5) 0.5405(6) 0.7211(4) 0.0072(11) Uani 1 1 d . . . . .
H1 H 0.874073 0.625169 0.747302 0.009 Uiso 1 1 calc R U . . .
C2 C 0.6151(6) 0.5949(5) 0.5840(5) 0.0095(8) Uani 1 1 d . . . . .
C3 C 0.8505(6) 0.3770(6) 0.6814(5) 0.0108(8) Uani 1 1 d . . . . .
H3A H 0.955193 0.341679 0.771181 0.013 Uiso 1 1 calc R U . . .
H3B H 0.754277 0.293253 0.662335 0.013 Uiso 1 1 calc R U . . .
C4 C 0.9095(6) 0.3865(5) 0.5457(5) 0.0094(8) Uani 1 1 d . . . . .
C5 C 0.8173(6) 0.3479(6) 0.3971(5) 0.0126(9) Uani 1 1 d . . . . .
H5 H 0.698647 0.301938 0.357783 0.015 Uiso 1 1 calc R U . . .
C6 C 1.0838(6) 0.4463(6) 0.4072(5) 0.0111(8) Uani 1 1 d . . . . .
H6 H 1.183843 0.480685 0.378418 0.013 Uiso 1 1 calc R U . . .
N1 N 0.7101(4) 0.5157(10) 0.8532(3) 0.0110(6) Uani 1 1 d . . . . .
H1A H 0.734876 0.412103 0.888656 0.016 Uiso 1 1 calc R U . . .
H1B H 0.587688 0.533049 0.821573 0.016 Uiso 1 1 calc R U . . .
H1C H 0.767491 0.586837 0.92961 0.016 Uiso 1 1 calc R U . . .
N2 N 1.0756(5) 0.4485(5) 0.5486(4) 0.0102(7) Uani 1 1 d . . . . .
H2N H 1.162341 0.483961 0.631045 0.012 Uiso 1 1 calc R U . . .
N3 N 0.9267(5) 0.3874(5) 0.3141(4) 0.0127(8) Uani 1 1 d . . . . .
H3N H 0.897394 0.375507 0.21411 0.015 Uiso 1 1 calc R U . . .
O1 O 0.6695(5) 0.6678(4) 0.4805(4) 0.0118(6) Uani 1 1 d . . . . .
H1O H 0.578247 0.696837 0.406038 0.018 Uiso 1 1 calc R U . . .
O2 O 0.4596(4) 0.5647(4) 0.5724(4) 0.0143(7) Uani 1 1 d . . . . .
F1 F 0.4176(5) 0.6784(4) 0.2154(4) 0.0163(7) Uani 1 1 d . . . . .
F2 F 0.5622(4) 0.4827(4) 0.0801(3) 0.0152(9) Uani 1 1 d . . . . .
F3 F 0.2437(7) 0.2975(6) -0.0309(5) 0.0188(9) Uani 1 1 d . . . . .
F4 F 0.0738(3) 0.4985(9) 0.0745(3) 0.0176(9) Uani 1 1 d . . . . .
F5 F 0.1934(5) 0.7240(6) -0.0290(5) 0.0170(9) Uani 1 1 d . . . . .
F6 F 0.3080(4) 0.5298(9) -0.1615(3) 0.0179(8) Uani 1 1 d . . . . .
F7 F 0.3734(5) 0.3840(5) 0.2389(4) 0.0180(8) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Ta1 F2 1.907(3) . ?
Ta1 F4 1.937(3) . ?
Ta1 F3 1.944(5) . ?
Ta1 F7 1.955(4) . ?
Ta1 F6 1.971(2) . ?
Ta1 F5 1.973(5) . ?
Ta1 F1 1.985(3) . ?
C1 N1 1.495(5) . ?
C1 C2 1.518(6) . ?
C1 C3 1.557(6) . ?
C1 H1 1 . ?
C2 O2 1.207(6) . ?
C2 O1 1.318(6) . ?
C3 C4 1.480(6) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.356(6) . ?
C4 N2 1.384(6) . ?
C5 N3 1.369(6) . ?
C5 H5 0.95 . ?
C6 N3 1.327(6) . ?
C6 N2 1.332(6) . ?
C6 H6 0.95 . ?
N1 H1A 0.91 . ?
N1 H1B 0.91 . ?
N1 H1C 0.91 . ?
N2 H2N 0.88 . ?
N3 H3N 0.88 . ?
O1 H1O 0.84 . ?

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
F2 Ta1 F4 162.10(18) . . ?
F2 Ta1 F3 93.08(17) . . ?
F4 Ta1 F3 80.8(2) . . ?
F2 Ta1 F7 82.42(13) . . ?
F4 Ta1 F7 79.88(17) . . ?
F3 Ta1 F7 78.22(17) . . ?
F2 Ta1 F6 78.84(12) . . ?
F4 Ta1 F6 115.37(11) . . ?
F3 Ta1 F6 75.8(2) . . ?
F7 Ta1 F6 146.8(2) . . ?
F2 Ta1 F5 119.73(14) . . ?
F4 Ta1 F5 76.3(2) . . ?
F3 Ta1 F5 128.64(14) . . ?
F7 Ta1 F5 139.36(16) . . ?
F6 Ta1 F5 73.8(2) . . ?
F2 Ta1 F1 81.05(13) . . ?
F4 Ta1 F1 97.5(2) . . ?
F3 Ta1 F1 155.52(16) . . ?
F7 Ta1 F1 77.45(15) . . ?
F6 Ta1 F1 125.5(2) . . ?
F5 Ta1 F1 73.62(16) . . ?
N1 C1 C2 107.8(3) . . ?
N1 C1 C3 109.6(4) . . ?
C2 C1 C3 109.0(3) . . ?
N1 C1 H1 110.1 . . ?
C2 C1 H1 110.1 . . ?
C3 C1 H1 110.1 . . ?
O2 C2 O1 126.3(4) . . ?
O2 C2 C1 122.4(4) . . ?
O1 C2 C1 111.2(4) . . ?
C4 C3 C1 113.8(4) . . ?
C4 C3 H3A 108.8 . . ?
C1 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C1 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 N2 106.0(4) . . ?
C5 C4 C3 129.7(4) . . ?
N2 C4 C3 124.3(4) . . ?
C4 C5 N3 107.3(4) . . ?
C4 C5 H5 126.3 . . ?
N3 C5 H5 126.3 . . ?
N3 C6 N2 107.5(4) . . ?
N3 C6 H6 126.3 . . ?
N2 C6 H6 126.3 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C6 N2 C4 109.6(4) . . ?
C6 N2 H2N 125.2 . . ?
C4 N2 H2N 125.2 . . ?
C6 N3 C5 109.7(4) . . ?
C6 N3 H3N 125.2 . . ?
C5 N3 H3N 125.2 . . ?
C2 O1 H1O 109.5 . . ?

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
N2 H2N F6 0.88 1.91 2.761(5) 163.4 1_656 yes
N3 H3N F4 0.88 2.41 2.968(5) 121.8 1_655 yes
N3 H3N F5 0.88 2.04 2.822(6) 147.4 2_645 yes
N1 H1A F5 0.91 1.98 2.853(9) 161.6 2_646 yes
N1 H1A F1 0.91 2.29 2.943(8) 128.1 2_646 yes
N1 H1B F6 0.91 2.24 3.097(4) 156.4 1_556 yes
N1 H1B O2 0.91 2.2 2.698(4) 114.1 . yes
N1 H1C F3 0.91 1.99 2.794(8) 147 2_656 yes
N1 H1C F4 0.91 2.42 2.882(4) 111.7 1_656 yes
O1 H1O F1 0.84 1.79 2.571(5) 154 . yes

