# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_R-Nb
_database_code_depnum_ccdc_archive 'CCDC 2151251'
loop_
_audit_author_name
_audit_author_address
'Kang Min Ok'
;Sogang University
South Korea
;
_audit_update_record             
;
2022-02-10 deposited with the CCDC.	2022-04-08 downloaded from the CCDC.
;

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

_chemical_formula_moiety         '2(C8 H10 N O3), F5 Nb O'
_chemical_formula_sum            'C16 H20 F5 N2 Nb O7'
_chemical_formula_weight         540.25
_chemical_absolute_configuration rmad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_Int_Tables_number      18
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   13.4517(5)
_cell_length_b                   7.4357(3)
_cell_length_c                   10.2751(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1027.74(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9017
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      28.35
_cell_measurement_wavelength     0.71076

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

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.099
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544

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

_exptl_absorpt_coefficient_mu    0.672
_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  0.688
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.817
_shelx_estimated_absorpt_T_max   0.936

#----------------------------------------------------------------------------#
#                   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      0.06222
_diffrn_orient_matrix_ub_12      -0.080478
_diffrn_orient_matrix_ub_13      -0.023718
_diffrn_orient_matrix_ub_21      -0.004174
_diffrn_orient_matrix_ub_22      0.033575
_diffrn_orient_matrix_ub_23      -0.069749
_diffrn_orient_matrix_ub_31      0.119154
_diffrn_orient_matrix_ub_32      0.043218
_diffrn_orient_matrix_ub_33      0.009951
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_number            36919
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.494
_diffrn_reflns_theta_max         28.388
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_coverage         0.719
_reflns_number_total             2575
_reflns_number_gt                2544
_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 2013/2 (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)+(0.0206P)²+0.3727P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2575
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0169
_refine_ls_R_factor_gt           0.0166
_refine_ls_wR_factor_ref         0.0433
_refine_ls_wR_factor_gt          0.0431
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1055 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.039(10)
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.05

#----------------------------------------------------------------------------#
#                   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
C1 C 0.65062(14) 0.6763(3) 0.22245(18) 0.0094(3) Uani 1 1 d . . . . .
H1 H 0.58388 0.729986 0.204328 0.011 Uiso 1 1 calc R U . . .
C2 C 0.66520(14) 0.6704(3) 0.36836(19) 0.0099(3) Uani 1 1 d . . . . .
C3 C 0.75754(13) 0.6288(3) 0.4221(2) 0.0124(3) Uani 1 1 d . . . . .
H3 H 0.812453 0.604497 0.366719 0.015 Uiso 1 1 calc R U . . .
C4 C 0.76962(14) 0.6228(3) 0.5562(2) 0.0130(3) Uani 1 1 d . . . . .
H4 H 0.832961 0.596431 0.592392 0.016 Uiso 1 1 calc R U . . .
C5 C 0.68901(15) 0.6554(3) 0.63760(19) 0.0116(4) Uani 1 1 d . . . . .
C6 C 0.59612(14) 0.6965(3) 0.58591(19) 0.0142(4) Uani 1 1 d . . . . .
H6 H 0.541092 0.718914 0.641536 0.017 Uiso 1 1 calc R U . . .
C7 C 0.58518(14) 0.7041(3) 0.45080(19) 0.0133(4) Uani 1 1 d . . . . .
H7 H 0.522153 0.73277 0.414609 0.016 Uiso 1 1 calc R U . . .
C8 C 0.65526(12) 0.4919(4) 0.15683(16) 0.0108(3) Uani 1 1 d . . . . .
N1 N 0.72761(13) 0.7888(2) 0.15560(17) 0.0120(3) Uani 1 1 d . . . . .
H1A H 0.712083 0.799153 0.069728 0.018 Uiso 1 1 calc R U . . .
H1B H 0.788191 0.73554 0.163905 0.018 Uiso 1 1 calc R U . . .
H1C H 0.729318 0.899946 0.192555 0.018 Uiso 1 1 calc R U . . .
O1 O 0.70649(11) 0.6403(2) 0.76861(14) 0.0148(3) Uani 1 1 d . . . . .
H1O H 0.655284 0.670743 0.809902 0.034(9) Uiso 1 1 calc R . . . .
O2 O 0.70796(11) 0.46472(17) 0.06339(15) 0.0169(3) Uani 1 1 d . . . . .
O3 O 0.59618(11) 0.3738(2) 0.21133(15) 0.0155(3) Uani 1 1 d . . . . .
H3O H 0.599839 0.275912 0.170795 0.023 Uiso 1 1 calc R U . . .
O4 O 0.41467(9) -0.10770(18) -0.18141(13) 0.0164(3) Uani 0.5 1 d . . P . .
F1 F 0.58600(9) 0.08099(16) 0.08613(12) 0.0160(2) Uani 1 1 d . . . . .
F2 F 0.42220(9) 0.22107(15) -0.05386(12) 0.0154(2) Uani 1 1 d . . . . .
F3 F 0.41467(9) -0.10770(18) -0.18141(13) 0.0164(3) Uani 0.5 1 d . . P . .
Nb1 Nb 0.5 0 -0.06508(2) 0.01238(7) Uani 1 2 d S T P . .



#----------------------------------------------------------------------------#
#                   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
C1 N1 1.498(2) . ?
C1 C2 1.513(3) . ?
C1 C8 1.529(3) . ?
C1 H1 1 . ?
C2 C7 1.392(3) . ?
C2 C3 1.394(3) . ?
C3 C4 1.388(3) . ?
C3 H3 0.95 . ?
C4 C5 1.391(3) . ?
C4 H4 0.95 . ?
C5 O1 1.371(2) . ?
C5 C6 1.392(3) . ?
C6 C7 1.397(3) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
C8 O2 1.210(2) . ?
C8 O3 1.310(3) . ?
N1 H1A 0.91 . ?
N1 H1B 0.91 . ?
N1 H1C 0.91 . ?
O1 H1O 0.84 . ?
O3 H3O 0.84 . ?
F1 Nb1 2.0285(12) . ?
F2 Nb1 1.9521(11) . ?
F3 Nb1 1.8405(13) . ?

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
N1 C1 C2 112.40(16) . . ?
N1 C1 C8 105.67(15) . . ?
C2 C1 C8 113.94(16) . . ?
N1 C1 H1 108.2 . . ?
C2 C1 H1 108.2 . . ?
C8 C1 H1 108.2 . . ?
C7 C2 C3 119.18(18) . . ?
C7 C2 C1 119.83(17) . . ?
C3 C2 C1 120.97(17) . . ?
C4 C3 C2 120.32(18) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.00(18) . . ?
C3 C4 H4 120 . . ?
C5 C4 H4 120 . . ?
O1 C5 C4 116.26(18) . . ?
O1 C5 C6 123.13(18) . . ?
C4 C5 C6 120.59(18) . . ?
C5 C6 C7 118.86(18) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C2 C7 C6 121.04(18) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
O2 C8 O3 125.6(2) . . ?
O2 C8 C1 121.6(2) . . ?
O3 C8 C1 112.82(15) . . ?
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 . . ?
C5 O1 H1O 109.5 . . ?
C8 O3 H3O 109.5 . . ?
F3 Nb1 O4 99.01(9) . 2_655 ?
F3 Nb1 F2 90.36(5) . 2_655 ?
O4 Nb1 F2 94.04(6) 2_655 2_655 ?
F3 Nb1 F2 94.04(6) . . ?
O4 Nb1 F2 90.36(5) 2_655 . ?
F2 Nb1 F2 173.23(7) 2_655 . ?
F3 Nb1 F1 169.18(6) . . ?
O4 Nb1 F1 90.72(5) 2_655 . ?
F2 Nb1 F1 84.21(5) 2_655 . ?
F2 Nb1 F1 90.60(5) . . ?
F3 Nb1 F1 90.72(5) . 2_655 ?
O4 Nb1 F1 169.18(6) 2_655 2_655 ?
F2 Nb1 F1 90.60(5) 2_655 2_655 ?
F2 Nb1 F1 84.20(5) . 2_655 ?
F1 Nb1 F1 80.02(7) . 2_655 ?

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 O2 0.91 2.13 2.743(2) 123.7 3_655 yes
N1 H1A F2 0.91 2.21 2.949(2) 137.6 2_665 yes
N1 H1B O4 0.91 1.96 2.866(2) 176.7 4 yes
N1 H1C O1 0.91 2.02 2.868(2) 153.5 3_656 yes
O1 H1O F2 0.84 1.92 2.7178(19) 157.7 2_666 yes
O3 H3O F1 0.84 1.7 2.5326(19) 170.3 . 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_S-Nb
_database_code_depnum_ccdc_archive 'CCDC 2151252'
loop_
_audit_author_name
_audit_author_address
'Kang Min Ok'
;Sogang University
South Korea
;
_audit_update_record             
;
2022-02-10 deposited with the CCDC.	2022-04-08 downloaded from the CCDC.
;

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

_chemical_formula_moiety         '2(C8 H10 N O3), F5 Nb O'
_chemical_formula_sum            'C16 H20 F5 N2 Nb O7'
_chemical_formula_weight         540.25
_chemical_absolute_configuration rmad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_Int_Tables_number      18
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   13.4489(7)
_cell_length_b                   7.4392(4)
_cell_length_c                   10.2681(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1027.31(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9817
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      28.36
_cell_measurement_wavelength     0.71076

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

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.084
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544

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

_exptl_absorpt_coefficient_mu    0.672
_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  0.704
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.847
_shelx_estimated_absorpt_T_max   0.946

#----------------------------------------------------------------------------#
#                   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      0.082112
_diffrn_orient_matrix_ub_12      0.069835
_diffrn_orient_matrix_ub_13      -0.025013
_diffrn_orient_matrix_ub_21      0.065723
_diffrn_orient_matrix_ub_22      -0.065763
_diffrn_orient_matrix_ub_23      -0.04108
_diffrn_orient_matrix_ub_31      -0.083712
_diffrn_orient_matrix_ub_32      0.016821
_diffrn_orient_matrix_ub_33      -0.056705
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0086
_diffrn_reflns_number            36962
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.029
_diffrn_reflns_theta_max         28.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_coverage         0.72
_reflns_number_total             2561
_reflns_number_gt                2546
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   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 2013/2 (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)+(0.0253P)²+0.4427P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2561
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.013
_refine_ls_R_factor_gt           0.0129
_refine_ls_wR_factor_ref         0.0372
_refine_ls_wR_factor_gt          0.0371
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_restrained_S_all      0.915
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1064 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.023(6)
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.29
_refine_diff_density_rms         0.041

#----------------------------------------------------------------------------#
#                   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
C1 C 0.34932(11) 0.3232(2) 0.77752(14) 0.0098(3) Uani 1 1 d . . . . .
H1 H 0.416087 0.269569 0.795615 0.012 Uiso 1 1 calc R U . . .
C2 C 0.33474(11) 0.3291(2) 0.63158(15) 0.0101(3) Uani 1 1 d . . . . .
C3 C 0.24228(11) 0.3709(2) 0.57791(16) 0.0124(3) Uani 1 1 d . . . . .
H3 H 0.187374 0.395127 0.633397 0.015 Uiso 1 1 calc R U . . .
C4 C 0.23024(11) 0.3771(2) 0.44368(16) 0.0134(3) Uani 1 1 d . . . . .
H4 H 0.16691 0.403571 0.407463 0.016 Uiso 1 1 calc R U . . .
C5 C 0.31083(12) 0.3446(2) 0.36233(16) 0.0117(3) Uani 1 1 d . . . . .
C6 C 0.40374(12) 0.3033(2) 0.41412(15) 0.0144(3) Uani 1 1 d . . . . .
H6 H 0.458751 0.280808 0.358426 0.017 Uiso 1 1 calc R U . . .
C7 C 0.41479(11) 0.2956(2) 0.54908(16) 0.0138(3) Uani 1 1 d . . . . .
H7 H 0.477861 0.26706 0.585242 0.017 Uiso 1 1 calc R U . . .
C8 C 0.34470(10) 0.5074(3) 0.84312(13) 0.0109(2) Uani 1 1 d . . . . .
N1 N 0.27250(10) 0.21086(19) 0.84438(13) 0.0122(3) Uani 1 1 d . . . . .
H1A H 0.288115 0.200386 0.930272 0.018 Uiso 1 1 calc R U . . .
H1B H 0.270753 0.09978 0.807331 0.018 Uiso 1 1 calc R U . . .
H1C H 0.211895 0.264074 0.836202 0.018 Uiso 1 1 calc R U . . .
O1 O 0.29335(9) 0.35954(17) 0.23108(11) 0.0150(2) Uani 1 1 d . . . . .
H1O H 0.344312 0.327762 0.18976 0.036(7) Uiso 1 1 calc R . . . .
O2 O 0.29211(9) 0.53475(15) 0.93667(12) 0.0173(2) Uani 1 1 d . . . . .
O3 O 0.40388(9) 0.62576(17) 0.78864(12) 0.0154(2) Uani 1 1 d . . . . .
H3O H 0.399717 0.723846 0.828794 0.023 Uiso 1 1 calc R U . . .
O4 O 0.58530(8) 1.10789(16) 1.18146(11) 0.0168(2) Uani 0.5 1 d . . P . .
F1 F 0.41410(7) 0.91845(13) 0.91363(10) 0.0162(2) Uani 1 1 d . . . . .
F2 F 0.57810(7) 0.77955(13) 1.05397(10) 0.01545(19) Uani 1 1 d . . . . .
F3 F 0.58530(8) 1.10789(16) 1.18146(11) 0.0168(2) Uani 0.5 1 d . . P . .
Nb1 Nb 0.5 1 1.06470(2) 0.01264(6) Uani 1 2 d S T P . .



#----------------------------------------------------------------------------#
#                   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
C1 N1 1.496(2) . ?
C1 C2 1.512(2) . ?
C1 C8 1.528(3) . ?
C1 H1 1 . ?
C2 C7 1.392(2) . ?
C2 C3 1.395(2) . ?
C3 C4 1.389(2) . ?
C3 H3 0.95 . ?
C4 C5 1.390(2) . ?
C4 H4 0.95 . ?
C5 O1 1.3726(19) . ?
C5 C6 1.392(2) . ?
C6 C7 1.395(2) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
C8 O2 1.2101(18) . ?
C8 O3 1.312(2) . ?
N1 H1A 0.91 . ?
N1 H1B 0.91 . ?
N1 H1C 0.91 . ?
O1 H1O 0.84 . ?
O3 H3O 0.84 . ?
F1 Nb1 2.0271(10) . ?
F2 Nb1 1.9506(9) . ?
F3 Nb1 1.8433(11) . ?

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
N1 C1 C2 112.43(13) . . ?
N1 C1 C8 105.70(12) . . ?
C2 C1 C8 113.93(13) . . ?
N1 C1 H1 108.2 . . ?
C2 C1 H1 108.2 . . ?
C8 C1 H1 108.2 . . ?
C7 C2 C3 119.25(14) . . ?
C7 C2 C1 119.84(14) . . ?
C3 C2 C1 120.90(14) . . ?
C4 C3 C2 120.23(14) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.99(14) . . ?
C3 C4 H4 120 . . ?
C5 C4 H4 120 . . ?
O1 C5 C4 116.26(14) . . ?
O1 C5 C6 123.14(15) . . ?
C4 C5 C6 120.58(15) . . ?
C5 C6 C7 118.96(15) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C2 C7 C6 120.97(14) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
O2 C8 O3 125.44(18) . . ?
O2 C8 C1 121.64(16) . . ?
O3 C8 C1 112.91(12) . . ?
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 . . ?
C5 O1 H1O 109.5 . . ?
C8 O3 H3O 109.5 . . ?
F3 Nb1 O4 98.85(7) . 2_675 ?
F3 Nb1 F2 90.33(5) . 2_675 ?
O4 Nb1 F2 93.88(5) 2_675 2_675 ?
F3 Nb1 F2 93.88(5) . . ?
O4 Nb1 F2 90.33(5) 2_675 . ?
F2 Nb1 F2 173.53(6) 2_675 . ?
F3 Nb1 F1 169.35(5) . . ?
O4 Nb1 F1 90.73(5) 2_675 . ?
F2 Nb1 F1 84.35(4) 2_675 . ?
F2 Nb1 F1 90.69(4) . . ?
F3 Nb1 F1 90.73(5) . 2_675 ?
O4 Nb1 F1 169.35(5) 2_675 2_675 ?
F2 Nb1 F1 90.69(4) 2_675 2_675 ?
F2 Nb1 F1 84.35(4) . 2_675 ?
F1 Nb1 F1 80.14(6) . 2_675 ?

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
C1 H1 O3 1 2.54 3.343(2) 136.7 2_665 yes
N1 H1A O2 0.91 2.13 2.7434(18) 123.6 3_547 yes
N1 H1A F2 0.91 2.21 2.9452(17) 137.7 2_665 yes
N1 H1B O1 0.91 2.02 2.8662(19) 153.5 3_546 yes
N1 H1C O4 0.91 1.96 2.8682(18) 176.7 4_467 yes
O1 H1O F2 0.84 1.92 2.7142(16) 158.3 2_664 yes
O3 H3O F1 0.84 1.7 2.5312(16) 169.5 . yes

