# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_H2Do2py2BF3
_database_code_depnum_ccdc_archive 'CCDC 2314190'
loop_
_audit_author_name
_audit_author_address
'Nathalie Saffon'
;Institut de Chimie de Toulouse
France
;
_audit_update_record             
;
2023-12-13 deposited with the CCDC.	2024-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H34 B2 F6 N6'
_chemical_formula_weight         518.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.5578(8)
_cell_length_b                   15.0808(10)
_cell_length_c                   15.1865(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.789(2)
_cell_angle_gamma                90
_cell_volume                     2490.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9690
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      28.66

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6753
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8-Venture CMOS detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            108499
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.029
_diffrn_reflns_theta_max         28.754
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6459
_reflns_number_gt                4806
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0499P)²+1.6926P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6459
_refine_ls_number_parameters     387
_refine_ls_number_restraints     126
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1321
_refine_ls_wR_factor_gt          0.1152
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
N1 N 0.24138(11) 0.69989(8) 0.25103(8) 0.0239(3) Uani 1 1 d . . . . .
N2 N 0.36971(13) 0.84241(8) 0.39117(9) 0.0276(3) Uani 1 1 d . . . . .
H2 H 0.3375(18) 0.8528(13) 0.3287(15) 0.039(5) Uiso 1 1 d . . . . .
N3 N 0.16417(14) 0.95240(9) 0.28853(9) 0.0337(3) Uani 1 1 d . . . . .
N4 N 0.03292(12) 0.81552(9) 0.14795(9) 0.0267(3) Uani 1 1 d . . . . .
H4 H 0.1160(18) 0.8310(12) 0.1663(13) 0.030(5) Uiso 1 1 d . . . . .
N5 N 0.16419(14) 0.53169(10) 0.09796(9) 0.0347(3) Uani 1 1 d . . . . .
N6 N 0.33447(15) 0.91806(9) 0.20054(10) 0.0362(3) Uani 1 1 d . . . . .
C1 C 0.31979(15) 0.68303(10) 0.34863(11) 0.0315(3) Uani 1 1 d . . . . .
H1A H 0.406015 0.674999 0.351528 0.038 Uiso 1 1 calc R U . . .
H1B H 0.292906 0.627680 0.370985 0.038 Uiso 1 1 calc R U . . .
C2 C 0.31282(15) 0.75912(10) 0.41157(11) 0.0296(3) Uani 1 1 d . . . . .
H2A H 0.225540 0.770737 0.403585 0.036 Uiso 1 1 calc R U . . .
H2B H 0.355333 0.741933 0.477579 0.036 Uiso 1 1 calc R U . . .
C3 C 0.33259(17) 0.92112(11) 0.43632(12) 0.0360(4) Uani 1 1 d . . . . .
H3A H 0.383882 0.972681 0.432817 0.043 Uiso 1 1 calc R U . . .
H3B H 0.348517 0.907944 0.503255 0.043 Uiso 1 1 calc R U . . .
C4 C 0.19830(18) 0.94503(11) 0.39029(11) 0.0362(4) Uani 1 1 d . . . . .
H4A H 0.146771 0.899080 0.405389 0.043 Uiso 1 1 calc R U . . .
H4B H 0.181828 1.002178 0.415878 0.043 Uiso 1 1 calc R U . . .
C5 C 0.03064(18) 0.95093(12) 0.24085(12) 0.0398(4) Uani 1 1 d . . . . .
H5A H 0.009842 0.986240 0.182589 0.048 Uiso 1 1 calc R U . . .
H5B H -0.010202 0.978765 0.281609 0.048 Uiso 1 1 calc R U . . .
C6 C -0.01729(16) 0.85770(11) 0.21717(11) 0.0324(4) Uani 1 1 d . . . . .
H6A H 0.006424 0.821621 0.275027 0.039 Uiso 1 1 calc R U . . .
H6B H -0.108197 0.859020 0.190643 0.039 Uiso 1 1 calc R U . . .
C7 C 0.02382(14) 0.71627(11) 0.14979(11) 0.0292(3) Uani 1 1 d . . . . .
H7A H 0.040704 0.691234 0.095105 0.035 Uiso 1 1 calc R U . . .
H7B H -0.060936 0.699323 0.144764 0.035 Uiso 1 1 calc R U . . .
C8 C 0.11341(13) 0.67736(10) 0.23853(10) 0.0249(3) Uani 1 1 d . . . . .
H8A H 0.093079 0.699584 0.292882 0.030 Uiso 1 1 calc R U . . .
H8B H 0.104308 0.612045 0.236759 0.030 Uiso 1 1 calc R U . . .
C9 C 0.28606(14) 0.65568(10) 0.18155(11) 0.0280(3) Uani 1 1 d . . . . .
H9A H 0.375759 0.665708 0.199705 0.034 Uiso 1 1 calc R U . . .
H9B H 0.246571 0.684200 0.119915 0.034 Uiso 1 1 calc R U . . .
C10 C 0.26193(14) 0.55687(10) 0.17096(11) 0.0275(3) Uani 1 1 d . . . . .
C11 C 0.33355(17) 0.49649(12) 0.23494(14) 0.0409(4) Uani 1 1 d . . . . .
H11 H 0.402748 0.516063 0.285632 0.049 Uiso 1 1 calc R U . . .
C12 C 0.30342(18) 0.40689(12) 0.22446(16) 0.0452(5) Uani 1 1 d . . . . .
H12 H 0.350275 0.364679 0.268640 0.054 Uiso 1 1 calc R U . . .
C13 C 0.20487(17) 0.38062(12) 0.14920(14) 0.0396(4) Uani 1 1 d . . . . .
H13 H 0.182933 0.319794 0.139292 0.048 Uiso 1 1 calc R U . . .
C14 C 0.13836(18) 0.44482(12) 0.08819(12) 0.0393(4) Uani 1 1 d . . . . .
H14 H 0.070134 0.426345 0.036125 0.047 Uiso 1 1 calc R U . . .
C15 C 0.50816(16) 0.83663(12) 0.41859(12) 0.0349(4) Uani 1 1 d . . . . .
H15A H 0.538932 0.895754 0.408724 0.042 Uiso 1 1 calc R U . . .
H15B H 0.527274 0.795090 0.374928 0.042 Uiso 1 1 calc R U . . .
C16 C 0.2251(2) 1.02748(11) 0.26008(13) 0.0426(4) Uani 1 1 d . . . . .
H16A H 0.287573 1.053093 0.316215 0.051 Uiso 1 1 calc R U . . .
H16B H 0.163476 1.074045 0.231500 0.051 Uiso 1 1 calc R U . . .
C17 C 0.28637(16) 0.99989(11) 0.19117(11) 0.0311(3) Uani 1 1 d . . . . .
C18 C 0.29564(16) 1.05888(12) 0.12356(12) 0.0365(4) Uani 1 1 d . . . . .
H18 H 0.261950 1.116834 0.119237 0.044 Uiso 1 1 calc R U . . .
C19 C 0.35466(16) 1.03191(14) 0.06264(12) 0.0409(4) Uani 1 1 d . . . . .
H19 H 0.362154 1.071038 0.015844 0.049 Uiso 1 1 calc R U . . .
C20 C 0.40237(16) 0.94743(13) 0.07096(12) 0.0381(4) Uani 1 1 d . . . . .
H20 H 0.442571 0.926935 0.029644 0.046 Uiso 1 1 calc R U . . .
C21 C 0.39053(17) 0.89317(12) 0.14058(12) 0.0376(4) Uani 1 1 d . . . . .
H21 H 0.423977 0.835053 0.146229 0.045 Uiso 1 1 calc R U . . .
C22 C -0.03246(17) 0.84915(14) 0.04952(11) 0.0404(4) Uani 1 1 d . . . . .
H22A H -0.045124 0.913873 0.052241 0.049 Uiso 1 1 calc R U . . .
H22B H -0.114548 0.820964 0.025122 0.049 Uiso 1 1 calc R U . . .
B1 B 0.58584(19) 0.80510(14) 0.52516(14) 0.0372(4) Uani 1 1 d . . . . .
F1 F 0.54353(12) 0.84630(9) 0.59152(8) 0.0579(3) Uani 1 1 d . . . . .
F2 F 0.57728(12) 0.71349(8) 0.53643(9) 0.0611(4) Uani 1 1 d . . . . .
F3 F 0.70893(11) 0.82824(10) 0.54481(10) 0.0655(4) Uani 1 1 d . . . . .
B2 B 0.04030(18) 0.83012(14) -0.02353(13) 0.0358(4) Uani 1 1 d D . . . .
F4 F 0.0295(7) 0.9001(4) -0.0832(4) 0.0778(15) Uani 0.48 1 d D U P A 1
F5 F 0.0064(4) 0.7521(4) -0.0697(3) 0.0598(13) Uani 0.48 1 d D U P A 1
F6 F 0.1687(3) 0.8208(3) 0.0296(3) 0.0401(10) Uani 0.48 1 d D U P A 1
F14 F -0.0439(8) 0.8492(8) -0.1159(5) 0.061(2) Uani 0.25 1 d D U P A 2
F15 F 0.1429(8) 0.8633(7) -0.0042(7) 0.072(2) Uani 0.25 1 d D U P A 2
F16 F 0.0553(9) 0.7319(5) -0.0380(6) 0.051(2) Uani 0.25 1 d D U P A 2
F24 F 0.1452(8) 0.7837(6) 0.0132(7) 0.069(2) Uani 0.27 1 d D U P A 3
F25 F -0.0373(8) 0.8011(7) -0.1061(6) 0.061(2) Uani 0.27 1 d D U P A 3
F26 F 0.0851(7) 0.9153(5) -0.0485(6) 0.0542(18) Uani 0.27 1 d D U P A 3


_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
N1 C8 1.4659(18) . ?
N1 C1 1.4742(19) . ?
N1 C9 1.4811(19) . ?
N2 C2 1.4979(19) . ?
N2 C3 1.504(2) . ?
N2 C15 1.513(2) . ?
N2 H2 0.91(2) . ?
N3 C4 1.464(2) . ?
N3 C5 1.466(2) . ?
N3 C16 1.473(2) . ?
N4 C7 1.501(2) . ?
N4 C6 1.5032(18) . ?
N4 C22 1.5158(19) . ?
N4 H4 0.934(19) . ?
N5 C14 1.341(2) . ?
N5 C10 1.342(2) . ?
N6 C21 1.338(2) . ?
N6 C17 1.341(2) . ?
C1 C2 1.513(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.514(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.509(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.513(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.515(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.383(2) . ?
C11 C12 1.391(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.371(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 B1 1.633(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.507(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.390(2) . ?
C18 C19 1.383(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.377(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.380(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 B2 1.628(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
B1 F3 1.395(2) . ?
B1 F2 1.400(2) . ?
B1 F1 1.405(2) . ?
B2 F15 1.227(6) . ?
B2 F25 1.344(7) . ?
B2 F24 1.346(7) . ?
B2 F5 1.358(4) . ?
B2 F4 1.369(4) . ?
B2 F6 1.436(4) . ?
B2 F14 1.440(7) . ?
B2 F26 1.481(7) . ?
B2 F16 1.516(7) . ?

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
C8 N1 C1 109.88(12) . . ?
C8 N1 C9 112.54(11) . . ?
C1 N1 C9 113.25(12) . . ?
C2 N2 C3 110.77(12) . . ?
C2 N2 C15 113.09(13) . . ?
C3 N2 C15 110.99(13) . . ?
C2 N2 H2 107.9(13) . . ?
C3 N2 H2 105.1(13) . . ?
C15 N2 H2 108.6(12) . . ?
C4 N3 C5 112.50(13) . . ?
C4 N3 C16 112.52(14) . . ?
C5 N3 C16 113.25(14) . . ?
C7 N4 C6 111.27(12) . . ?
C7 N4 C22 109.71(13) . . ?
C6 N4 C22 111.51(12) . . ?
C7 N4 H4 108.3(11) . . ?
C6 N4 H4 106.7(11) . . ?
C22 N4 H4 109.2(11) . . ?
C14 N5 C10 117.48(15) . . ?
C21 N6 C17 117.71(15) . . ?
N1 C1 C2 110.99(12) . . ?
N1 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
N1 C1 H1B 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
N2 C2 C1 112.60(13) . . ?
N2 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
N2 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
N2 C3 C4 112.55(13) . . ?
N2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
N2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
N3 C4 C3 111.91(14) . . ?
N3 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
N3 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
N3 C5 C6 111.83(13) . . ?
N3 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
N3 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
N4 C6 C5 111.31(13) . . ?
N4 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
N4 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N4 C7 C8 111.85(12) . . ?
N4 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N4 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N1 C8 C7 112.44(12) . . ?
N1 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N1 C9 C10 114.99(12) . . ?
N1 C9 H9A 108.5 . . ?
C10 C9 H9A 108.5 . . ?
N1 C9 H9B 108.5 . . ?
C10 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
N5 C10 C11 122.01(15) . . ?
N5 C10 C9 116.06(14) . . ?
C11 C10 C9 121.88(15) . . ?
C10 C11 C12 119.47(17) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 118.77(18) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C14 118.28(16) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?
N5 C14 C13 123.97(17) . . ?
N5 C14 H14 118.0 . . ?
C13 C14 H14 118.0 . . ?
N2 C15 B1 117.69(13) . . ?
N2 C15 H15A 107.9 . . ?
B1 C15 H15A 107.9 . . ?
N2 C15 H15B 107.9 . . ?
B1 C15 H15B 107.9 . . ?
H15A C15 H15B 107.2 . . ?
N3 C16 C17 112.04(13) . . ?
N3 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
N3 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N6 C17 C18 122.31(16) . . ?
N6 C17 C16 117.11(14) . . ?
C18 C17 C16 120.55(16) . . ?
C19 C18 C17 118.99(17) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C20 C19 C18 118.91(16) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C21 118.58(16) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
N6 C21 C20 123.48(18) . . ?
N6 C21 H21 118.3 . . ?
C20 C21 H21 118.3 . . ?
N4 C22 B2 114.39(13) . . ?
N4 C22 H22A 108.7 . . ?
B2 C22 H22A 108.7 . . ?
N4 C22 H22B 108.7 . . ?
B2 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
F3 B1 F2 109.26(17) . . ?
F3 B1 F1 108.25(15) . . ?
F2 B1 F1 107.01(16) . . ?
F3 B1 C15 108.53(15) . . ?
F2 B1 C15 111.75(15) . . ?
F1 B1 C15 111.96(16) . . ?
F25 B2 F24 116.1(6) . . ?
F5 B2 F4 112.4(3) . . ?
F5 B2 F6 105.5(3) . . ?
F4 B2 F6 107.0(4) . . ?
F15 B2 F14 115.5(6) . . ?
F25 B2 F26 102.9(4) . . ?
F24 B2 F26 102.3(5) . . ?
F15 B2 F16 106.5(6) . . ?
F14 B2 F16 97.3(5) . . ?
F15 B2 C22 116.4(4) . . ?
F25 B2 C22 111.0(3) . . ?
F24 B2 C22 114.2(4) . . ?
F5 B2 C22 112.3(2) . . ?
F4 B2 C22 111.3(2) . . ?
F6 B2 C22 107.9(2) . . ?
F14 B2 C22 107.1(3) . . ?
F26 B2 C22 109.1(4) . . ?
F16 B2 C22 112.4(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
N2 H2 N3 0.91(2) 2.41(2) 2.884(2) 112.6(15) . yes
N2 H2 N6 0.91(2) 2.17(2) 3.0084(19) 153.1(17) . yes
N4 H4 N3 0.934(19) 2.532(18) 2.988(2) 110.3(13) . yes

_refine_diff_density_max         0.399
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.049


####################################################################### 
# 
# 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_H4Do2py2BF3+
_database_code_depnum_ccdc_archive 'CCDC 2314191'
loop_
_audit_author_name
_audit_author_address
'Nathalie Saffon'
;Institut de Chimie de Toulouse
France
;
_audit_update_record             
;
2023-12-13 deposited with the CCDC.	2024-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H36 B2 F6 I6 N6'
_chemical_formula_weight         1281.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.8808(5)
_cell_length_b                   12.9692(5)
_cell_length_c                   13.6306(5)
_cell_angle_alpha                75.784(3)
_cell_angle_beta                 67.305(3)
_cell_angle_gamma                60.961(3)
_cell_volume                     1831.86(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    6292
_cell_measurement_theta_min      3.52
_cell_measurement_theta_max      66.53

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.323
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    40.430
_shelx_estimated_absorpt_T_min   0.195
_shelx_estimated_absorpt_T_max   0.499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3939
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_special_details   
;
SADABS-2016/2 Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'incoatec microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8-Venture Photon III detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 768x1024
_diffrn_reflns_number            6486
_diffrn_reflns_av_unetI/netI     0.1010
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.524
_diffrn_reflns_theta_max         66.770
_diffrn_reflns_theta_full        66.770
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6486
_reflns_number_gt                4270
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component 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)+(0.0524P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6486
_refine_ls_number_parameters     392
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1381
_refine_ls_wR_factor_gt          0.1187
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
I1 I -0.18105(8) 0.62398(7) 0.34656(7) 0.0424(2) Uani 1 1 d . . . . .
I2 I 0.01765(8) 0.36022(8) 0.35342(7) 0.0435(2) Uani 1 1 d . . . . .
I3 I 0.18900(9) 0.11896(8) 0.35804(7) 0.0485(3) Uani 1 1 d . . . . .
I4 I 0.04886(9) 0.69767(8) 0.32429(7) 0.0488(3) Uani 1 1 d . . . . .
I5 I 0.22413(8) 0.76009(8) 0.33269(7) 0.0454(2) Uani 1 1 d . . . . .
I6 I 0.44411(7) 0.82259(7) 0.34455(6) 0.0348(2) Uani 1 1 d . . . . .
B1 B 0.5400(14) 0.6474(13) 0.8958(12) 0.037(4) Uani 1 1 d . . . . .
F1 F 0.5947(7) 0.5234(6) 0.8946(5) 0.0468(19) Uani 1 1 d . . . . .
F2 F 0.5519(7) 0.6783(6) 0.9799(6) 0.0467(19) Uani 1 1 d . . . . .
F3 F 0.4088(6) 0.6874(6) 0.9117(5) 0.0397(17) Uani 1 1 d . . . . .
B2 B 0.0354(15) 0.8613(17) 0.9061(12) 0.046(4) Uani 1 1 d . . . . .
F4 F 0.1556(6) 0.8168(6) 0.9209(5) 0.0390(17) Uani 1 1 d . . . . .
F5 F -0.0343(7) 0.8139(8) 0.9897(6) 0.057(2) Uani 1 1 d . . . . .
F6 F -0.0191(7) 0.9840(7) 0.9070(6) 0.050(2) Uani 1 1 d . . . . .
N1 N 0.3193(9) 0.9483(8) 0.7112(7) 0.028(2) Uani 1 1 d . . . . .
N2 N 0.5392(9) 0.7180(8) 0.7016(7) 0.028(2) Uani 1 1 d . . . . .
H2 H 0.442(11) 0.748(10) 0.741(10) 0.042 Uiso 1 1 d . U . . .
N3 N 0.3937(8) 0.5977(8) 0.7046(7) 0.026(2) Uani 1 1 d . . . . .
N4 N 0.1731(10) 0.8269(9) 0.7103(7) 0.032(2) Uani 1 1 d . . . . .
H4 H 0.229(12) 0.800(11) 0.746(11) 0.049 Uiso 1 1 d . U . . .
N5 N 0.2738(10) 0.9331(9) 0.9482(9) 0.036(3) Uani 1 1 d . . . . .
H5 H 0.228(13) 0.896(12) 0.954(11) 0.054 Uiso 1 1 d . U . . .
N6 N 0.2725(10) 0.5640(9) 0.9444(9) 0.039(3) Uani 1 1 d D . . . .
H6 H 0.310(11) 0.606(10) 0.938(11) 0.058 Uiso 1 1 d D U . . .
C1 C 0.4474(11) 0.9367(10) 0.6615(9) 0.033(3) Uani 1 1 d . . . . .
H1A H 0.474393 0.948082 0.715270 0.040 Uiso 1 1 calc R U . . .
H1B H 0.448160 0.999990 0.603573 0.040 Uiso 1 1 calc R U . . .
C2 C 0.5392(12) 0.8189(11) 0.6164(9) 0.036(3) Uani 1 1 d . . . . .
H2A H 0.624152 0.815282 0.586311 0.043 Uiso 1 1 calc R U . . .
H2B H 0.517243 0.810115 0.557832 0.043 Uiso 1 1 calc R U . . .
C3 C 0.5999(10) 0.6015(10) 0.6533(9) 0.033(3) Uani 1 1 d . . . . .
H3A H 0.674713 0.596349 0.591633 0.039 Uiso 1 1 calc R U . . .
H3B H 0.627281 0.535877 0.706644 0.039 Uiso 1 1 calc R U . . .
C4 C 0.5104(11) 0.5892(11) 0.6174(8) 0.034(3) Uani 1 1 d . . . . .
H4A H 0.488157 0.651803 0.560478 0.041 Uiso 1 1 calc R U . . .
H4B H 0.552494 0.511878 0.586589 0.041 Uiso 1 1 calc R U . . .
C5 C 0.2965(11) 0.6193(10) 0.6596(9) 0.032(3) Uani 1 1 d . . . . .
H5A H 0.233286 0.595419 0.714601 0.038 Uiso 1 1 calc R U . . .
H5B H 0.335498 0.569459 0.598951 0.038 Uiso 1 1 calc R U . . .
C6 C 0.2314(11) 0.7486(9) 0.6215(9) 0.028(3) Uani 1 1 d . . . . .
H6A H 0.293109 0.771255 0.562633 0.034 Uiso 1 1 calc R U . . .
H6B H 0.166154 0.758797 0.593715 0.034 Uiso 1 1 calc R U . . .
C7 C 0.1456(12) 0.9529(11) 0.6674(9) 0.037(3) Uani 1 1 d . . . . .
H7A H 0.110647 0.971915 0.608566 0.044 Uiso 1 1 calc R U . . .
H7B H 0.081371 1.006210 0.724494 0.044 Uiso 1 1 calc R U . . .
C8 C 0.2594(11) 0.9756(11) 0.6271(8) 0.033(3) Uani 1 1 d . . . . .
H8A H 0.235351 1.059626 0.600467 0.039 Uiso 1 1 calc R U . . .
H8B H 0.321140 0.926596 0.566427 0.039 Uiso 1 1 calc R U . . .
C9 C 0.2430(12) 1.0454(11) 0.7836(10) 0.041(3) Uani 1 1 d . . . . .
H9A H 0.154618 1.058990 0.807692 0.049 Uiso 1 1 calc R U . . .
H9B H 0.247465 1.118709 0.743372 0.049 Uiso 1 1 calc R U . . .
C10 C 0.2830(10) 1.0222(10) 0.8791(9) 0.031(3) Uani 1 1 d . . . . .
C11 C 0.3258(12) 1.0925(12) 0.9019(11) 0.042(3) Uani 1 1 d . . . . .
H11 H 0.339061 1.154264 0.852612 0.051 Uiso 1 1 calc R U . . .
C12 C 0.3476(12) 1.0682(14) 0.9987(12) 0.051(4) Uani 1 1 d . . . . .
H12 H 0.374150 1.115770 1.016894 0.061 Uiso 1 1 calc R U . . .
C13 C 0.3318(13) 0.9769(13) 1.0692(11) 0.048(4) Uani 1 1 d . . . . .
H13 H 0.346138 0.961938 1.135736 0.057 Uiso 1 1 calc R U . . .
C14 C 0.2956(12) 0.9088(12) 1.0420(10) 0.045(4) Uani 1 1 d . . . . .
H14 H 0.285572 0.844318 1.088818 0.054 Uiso 1 1 calc R U . . .
C15 C 0.5950(12) 0.7107(11) 0.7838(10) 0.040(3) Uani 1 1 d . . . . .
H15A H 0.575771 0.791406 0.795392 0.048 Uiso 1 1 calc R U . . .
H15B H 0.687073 0.665369 0.757053 0.048 Uiso 1 1 calc R U . . .
C16 C 0.4227(13) 0.4851(11) 0.7739(10) 0.046(3) Uani 1 1 d . . . . .
H16A H 0.492335 0.469350 0.798599 0.055 Uiso 1 1 calc R U . . .
H16B H 0.450611 0.419075 0.731537 0.055 Uiso 1 1 calc R U . . .
C17 C 0.3111(12) 0.4892(10) 0.8698(10) 0.033(3) Uani 1 1 d . . . . .
C18 C 0.2559(12) 0.4171(11) 0.8884(11) 0.040(3) Uani 1 1 d . . . . .
H18 H 0.282512 0.364723 0.836466 0.048 Uiso 1 1 calc R U . . .
C19 C 0.1608(13) 0.4191(12) 0.9825(12) 0.050(4) Uani 1 1 d . . . . .
H19 H 0.121320 0.369281 0.995253 0.060 Uiso 1 1 calc R U . . .
C20 C 0.1234(12) 0.4977(11) 1.0601(11) 0.045(3) Uani 1 1 d . . . . .
H20 H 0.059722 0.500408 1.126191 0.054 Uiso 1 1 calc R U . . .
C21 C 0.1826(11) 0.5691(12) 1.0357(10) 0.038(3) Uani 1 1 d . . . . .
H21 H 0.158511 0.623072 1.085275 0.046 Uiso 1 1 calc R U . . .
C22 C 0.0601(12) 0.8172(12) 0.7964(9) 0.039(3) Uani 1 1 d . . . . .
H22A H 0.073487 0.733869 0.807816 0.046 Uiso 1 1 calc R U . . .
H22B H -0.014594 0.865256 0.772530 0.046 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I2 3.1287(12) . ?
I2 I3 2.8235(13) . ?
I4 I5 2.7901(14) . ?
B1 F2 1.386(16) . ?
B1 F1 1.409(16) . ?
B1 F3 1.446(16) . ?
B1 C15 1.619(19) . ?
B2 F5 1.373(18) . ?
B2 F6 1.394(19) . ?
B2 F4 1.443(16) . ?
B2 C22 1.594(19) . ?
N1 C1 1.466(15) . ?
N1 C9 1.478(14) . ?
N1 C8 1.501(13) . ?
N2 C3 1.508(14) . ?
N2 C15 1.511(14) . ?
N2 C2 1.521(14) . ?
N2 H2 1.06(12) . ?
N3 C5 1.481(14) . ?
N3 C4 1.486(14) . ?
N3 C16 1.493(14) . ?
N4 C6 1.492(13) . ?
N4 C7 1.505(15) . ?
N4 C22 1.517(15) . ?
N4 H4 0.90(12) . ?
N5 C10 1.323(16) . ?
N5 C14 1.343(16) . ?
N5 H5 0.91(14) . ?
N6 C21 1.321(16) . ?
N6 C17 1.361(15) . ?
N6 H6 0.852(10) . ?
C1 C2 1.502(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.498(16) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.526(15) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.501(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.492(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.411(17) . ?
C11 C12 1.385(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.37(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.354(19) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.512(17) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.355(17) . ?
C18 C19 1.385(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.432(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.375(18) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?

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
I3 I2 I1 177.20(4) . . ?
F2 B1 F1 110.4(10) . . ?
F2 B1 F3 109.2(11) . . ?
F1 B1 F3 105.7(11) . . ?
F2 B1 C15 111.1(12) . . ?
F1 B1 C15 112.9(12) . . ?
F3 B1 C15 107.3(10) . . ?
F5 B2 F6 111.0(12) . . ?
F5 B2 F4 107.6(12) . . ?
F6 B2 F4 106.8(12) . . ?
F5 B2 C22 110.3(13) . . ?
F6 B2 C22 113.6(12) . . ?
F4 B2 C22 107.2(11) . . ?
C1 N1 C9 110.6(9) . . ?
C1 N1 C8 110.1(9) . . ?
C9 N1 C8 108.3(9) . . ?
C3 N2 C15 111.7(9) . . ?
C3 N2 C2 111.7(9) . . ?
C15 N2 C2 113.1(9) . . ?
C3 N2 H2 113(7) . . ?
C15 N2 H2 106(6) . . ?
C2 N2 H2 100(6) . . ?
C5 N3 C4 110.2(9) . . ?
C5 N3 C16 110.6(9) . . ?
C4 N3 C16 108.7(9) . . ?
C6 N4 C7 110.7(9) . . ?
C6 N4 C22 114.8(10) . . ?
C7 N4 C22 111.9(9) . . ?
C6 N4 H4 107(8) . . ?
C7 N4 H4 110(9) . . ?
C22 N4 H4 103(9) . . ?
C10 N5 C14 124.4(12) . . ?
C10 N5 H5 127(9) . . ?
C14 N5 H5 106(9) . . ?
C21 N6 C17 122.4(12) . . ?
C21 N6 H6 116(10) . . ?
C17 N6 H6 121(10) . . ?
N1 C1 C2 113.1(10) . . ?
N1 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C1 C2 N2 111.2(9) . . ?
C1 C2 H2A 109.4 . . ?
N2 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
N2 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 N2 110.7(9) . . ?
C4 C3 H3A 109.5 . . ?
N2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
N3 C4 C3 113.4(9) . . ?
N3 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
N3 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
N3 C5 C6 112.5(10) . . ?
N3 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N3 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
N4 C6 C5 110.8(9) . . ?
N4 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 N4 112.8(10) . . ?
C8 C7 H7A 109.0 . . ?
N4 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
N4 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 N1 112.7(9) . . ?
C7 C8 H8A 109.0 . . ?
N1 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
N1 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
N1 C9 C10 113.8(9) . . ?
N1 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
N5 C10 C11 118.1(11) . . ?
N5 C10 C9 118.1(12) . . ?
C11 C10 C9 123.7(12) . . ?
C12 C11 C10 117.6(13) . . ?
C12 C11 H11 121.2 . . ?
C10 C11 H11 121.2 . . ?
C13 C12 C11 121.5(13) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 118.8(12) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
N5 C14 C13 119.5(14) . . ?
N5 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
N2 C15 B1 111.1(10) . . ?
N2 C15 H15A 109.4 . . ?
B1 C15 H15A 109.4 . . ?
N2 C15 H15B 109.4 . . ?
B1 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
N3 C16 C17 112.3(10) . . ?
N3 C16 H16A 109.1 . . ?
C17 C16 H16A 109.1 . . ?
N3 C16 H16B 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
C18 C17 N6 119.4(12) . . ?
C18 C17 C16 123.9(12) . . ?
N6 C17 C16 116.4(11) . . ?
C17 C18 C19 120.6(13) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C20 118.7(13) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 H19 120.7 . . ?
C21 C20 C19 117.7(13) . . ?
C21 C20 H20 121.1 . . ?
C19 C20 H20 121.1 . . ?
N6 C21 C20 121.2(13) . . ?
N6 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
N4 C22 B2 111.8(10) . . ?
N4 C22 H22A 109.3 . . ?
B2 C22 H22A 109.3 . . ?
N4 C22 H22B 109.3 . . ?
B2 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?

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 H2 N1 1.06(12) 2.33(11) 2.942(13) 115(8) . yes
N4 H4 F4 0.90(12) 2.23(13) 2.766(11) 118(10) . yes
N4 H4 N3 0.90(12) 2.47(12) 2.943(13) 113(10) . yes
N5 H5 F4 0.91(14) 1.89(14) 2.770(13) 162(13) . yes
N6 H6 F3 0.852(10) 1.91(2) 2.759(13) 174(14) . yes
C2 H2A I3 0.99 3.29 4.104(13) 140.8 2_666 yes
C3 H3A I1 0.99 3.16 4.077(12) 154.1 1_655 yes
C3 H3B F1 0.99 2.41 3.180(14) 134.3 . yes
C4 H4A I6 0.99 3.28 4.259(12) 170.3 . yes
C6 H6A I6 0.99 2.98 3.933(11) 161.6 . yes
C6 H6B I2 0.99 3.19 3.964(12) 135.9 2_566 yes
C7 H7B F6 0.99 2.34 3.130(14) 136.3 . yes
C8 H8B I6 0.99 3.12 4.066(11) 161.2 . yes
C9 H9A F6 0.99 2.63 3.526(17) 150.6 . yes
C9 H9B I1 0.99 3.07 4.025(13) 163.6 2_576 yes
C11 H11 I6 0.95 3.12 3.867(13) 136.6 2_676 yes
C13 H13 I6 0.95 3.32 4.228(13) 161.8 1_556 yes
C14 H14 I5 0.95 3.15 3.928(13) 140.7 1_556 yes
C16 H16A F1 0.99 2.57 3.484(17) 153.0 . yes
C16 H16B I6 0.99 3.02 3.982(13) 164.1 2_666 yes
C18 H18 I1 0.95 3.18 3.897(13) 133.8 2_566 yes
C20 H20 I2 0.95 3.18 3.959(13) 140.9 1_556 yes
C21 H21 I4 0.95 3.20 4.053(13) 150.9 1_556 yes
C22 H22B I3 0.99 3.27 4.146(12) 148.0 2_566 yes

_refine_diff_density_max         1.491
_refine_diff_density_min         -1.315
_refine_diff_density_rms         0.212


####################################################################### 
# 
# 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_Zn(Do2py2BF3)
_database_code_depnum_ccdc_archive 'CCDC 2314192'
loop_
_audit_author_name
_audit_author_address
'Nathalie Saffon'
;Institut de Chimie de Toulouse
France
;
_audit_update_record             
;
2023-12-13 deposited with the CCDC.	2024-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H36 B2 F6 N6 O2 Zn'
_chemical_formula_weight         617.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   17.1147(8)
_cell_length_b                   9.0627(5)
_cell_length_c                   16.9949(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2636.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.008
_shelx_estimated_absorpt_T_min   0.787
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6317
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_special_details   
;
SADABS-2016/2 - Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8-Venture Photon III-C14 detector'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            64889
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.274
_diffrn_reflns_theta_max         28.310
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             6090
_reflns_number_gt                5529
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_max     0.851
_reflns_Friedel_fraction_full    0.912

_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. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 20158)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0205P)²+0.6837P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2260 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.006(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6090
_refine_ls_number_parameters     376
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0521
_refine_ls_wR_factor_gt          0.0499
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Zn1 Zn 0.70854(2) 0.52406(2) 0.47123(2) 0.01847(6) Uani 1 1 d . . . . .
F1 F 0.91101(10) 0.17422(18) 0.41181(14) 0.0522(5) Uani 1 1 d . . . . .
F2 F 0.89935(10) 0.2796(2) 0.29111(12) 0.0471(4) Uani 1 1 d . . . . .
F3 F 0.88561(9) 0.41978(17) 0.40165(10) 0.0317(3) Uani 1 1 d . . . . .
F4 F 0.66080(9) 0.60997(16) 0.66130(10) 0.0318(3) Uani 1 1 d . . . . .
F5 F 0.68242(11) 0.84984(18) 0.69572(10) 0.0410(4) Uani 1 1 d . . . . .
F6 F 0.55810(10) 0.76061(19) 0.69035(10) 0.0430(4) Uani 1 1 d . . . . .
N1 N 0.72396(11) 0.6824(2) 0.37271(12) 0.0204(4) Uani 1 1 d . . . . .
N2 N 0.72004(11) 0.3666(2) 0.36404(12) 0.0222(4) Uani 1 1 d . . . . .
N3 N 0.60447(11) 0.3784(2) 0.49174(11) 0.0221(5) Uani 1 1 d . . . . .
N4 N 0.61067(11) 0.6938(2) 0.50124(12) 0.0202(4) Uani 1 1 d . . . . .
N5 N 0.80346(11) 0.6667(2) 0.51078(12) 0.0199(4) Uani 1 1 d . . . . .
N6 N 0.74978(12) 0.3619(2) 0.55547(13) 0.0214(4) Uani 1 1 d . . . . .
C1 C 0.70247(14) 0.6089(3) 0.29824(14) 0.0248(5) Uani 1 1 d . . . . .
H1A H 0.720872 0.669119 0.253322 0.030 Uiso 1 1 calc R U . . .
H1B H 0.644884 0.600978 0.294693 0.030 Uiso 1 1 calc R U . . .
C2 C 0.73841(15) 0.4554(3) 0.29331(15) 0.0252(5) Uani 1 1 d . . . . .
H2A H 0.718237 0.404288 0.246002 0.030 Uiso 1 1 calc R U . . .
H2B H 0.795809 0.464344 0.287873 0.030 Uiso 1 1 calc R U . . .
C3 C 0.63938(14) 0.3078(3) 0.35651(16) 0.0259(5) Uani 1 1 d . . . . .
H3A H 0.639327 0.224740 0.318686 0.031 Uiso 1 1 calc R U . . .
H3B H 0.604834 0.385958 0.335365 0.031 Uiso 1 1 calc R U . . .
C4 C 0.60770(15) 0.2553(3) 0.43440(15) 0.0258(5) Uani 1 1 d . . . . .
H4A H 0.554615 0.214318 0.426803 0.031 Uiso 1 1 calc R U . . .
H4B H 0.641527 0.175807 0.455269 0.031 Uiso 1 1 calc R U . . .
C5 C 0.53239(12) 0.4668(3) 0.4811(2) 0.0248(6) Uani 1 1 d . . . . .
H5A H 0.487045 0.410938 0.501626 0.030 Uiso 1 1 calc R U . . .
H5B H 0.523687 0.484713 0.424291 0.030 Uiso 1 1 calc R U . . .
C6 C 0.53861(13) 0.6133(3) 0.52381(16) 0.0247(5) Uani 1 1 d . . . . .
H6A H 0.492423 0.674578 0.511140 0.030 Uiso 1 1 calc R U . . .
H6B H 0.538851 0.595592 0.581294 0.030 Uiso 1 1 calc R U . . .
C7 C 0.59736(14) 0.7667(3) 0.42414(15) 0.0240(5) Uani 1 1 d . . . . .
H7A H 0.563908 0.854665 0.431811 0.029 Uiso 1 1 calc R U . . .
H7B H 0.569461 0.697892 0.388687 0.029 Uiso 1 1 calc R U . . .
C8 C 0.67327(15) 0.8129(3) 0.38632(15) 0.0235(5) Uani 1 1 d . . . . .
H8A H 0.662395 0.862389 0.335562 0.028 Uiso 1 1 calc R U . . .
H8B H 0.700624 0.884038 0.420893 0.028 Uiso 1 1 calc R U . . .
C9 C 0.80661(14) 0.7291(3) 0.37274(15) 0.0240(5) Uani 1 1 d . . . . .
H9A H 0.812314 0.821113 0.341847 0.029 Uiso 1 1 calc R U . . .
H9B H 0.839140 0.651963 0.347712 0.029 Uiso 1 1 calc R U . . .
C10 C 0.83411(13) 0.7548(2) 0.45567(13) 0.0204(5) Uani 1 1 d . . . . .
C11 C 0.88944(12) 0.8619(2) 0.4733(2) 0.0264(5) Uani 1 1 d . . . . .
H11 H 0.909575 0.924243 0.433234 0.032 Uiso 1 1 calc R U . . .
C12 C 0.91470(15) 0.8761(3) 0.55003(18) 0.0304(6) Uani 1 1 d . . . . .
H12 H 0.952478 0.948678 0.563419 0.037 Uiso 1 1 calc R U . . .
C13 C 0.88452(14) 0.7838(3) 0.60727(16) 0.0286(5) Uani 1 1 d . . . . .
H13 H 0.901803 0.790098 0.660281 0.034 Uiso 1 1 calc R U . . .
C14 C 0.82849(15) 0.6820(3) 0.58514(15) 0.0240(5) Uani 1 1 d . . . . .
H14 H 0.806688 0.619895 0.624466 0.029 Uiso 1 1 calc R U . . .
C15 C 0.77640(14) 0.2410(3) 0.37148(16) 0.0264(5) Uani 1 1 d . . . . .
H15A H 0.765550 0.170372 0.328422 0.032 Uiso 1 1 calc R U . . .
H15B H 0.765393 0.189557 0.421653 0.032 Uiso 1 1 calc R U . . .
C16 C 0.61119(14) 0.3205(3) 0.57250(15) 0.0239(5) Uani 1 1 d . . . . .
H16A H 0.577278 0.232733 0.578482 0.029 Uiso 1 1 calc R U . . .
H16B H 0.593470 0.396346 0.610450 0.029 Uiso 1 1 calc R U . . .
C17 C 0.69475(14) 0.2791(3) 0.58987(15) 0.0213(5) Uani 1 1 d . . . . .
C18 C 0.71313(15) 0.1622(3) 0.63904(15) 0.0259(5) Uani 1 1 d . . . . .
H18 H 0.672911 0.104338 0.662107 0.031 Uiso 1 1 calc R U . . .
C19 C 0.79059(16) 0.1309(3) 0.65408(16) 0.0306(6) Uani 1 1 d . . . . .
H19 H 0.804495 0.051006 0.687446 0.037 Uiso 1 1 calc R U . . .
C20 C 0.84773(16) 0.2178(3) 0.61976(15) 0.0291(6) Uani 1 1 d . . . . .
H20 H 0.901495 0.200110 0.629959 0.035 Uiso 1 1 calc R U . . .
C21 C 0.82502(15) 0.3301(3) 0.57072(14) 0.0248(5) Uani 1 1 d . . . . .
H21 H 0.864350 0.388274 0.546337 0.030 Uiso 1 1 calc R U . . .
C22 C 0.62915(15) 0.8079(3) 0.56214(14) 0.0228(5) Uani 1 1 d . . . . .
H22A H 0.589164 0.886544 0.558411 0.027 Uiso 1 1 calc R U . . .
H22B H 0.680012 0.853028 0.548309 0.027 Uiso 1 1 calc R U . . .
B1 B 0.86864(17) 0.2802(3) 0.3693(2) 0.0303(6) Uani 1 1 d . . . . .
B2 B 0.63362(18) 0.7553(3) 0.65257(18) 0.0274(6) Uani 1 1 d . . . . .
O1 O 1.01289(15) 0.4849(3) 0.24200(19) 0.0570(8) Uani 1 1 d . . . . .
H1C H 0.991(3) 0.554(5) 0.229(3) 0.079(17) Uiso 1 1 d . . . . .
H1D H 0.975(3) 0.425(5) 0.256(3) 0.079(14) Uiso 1 1 d . . . . .
O2 O 0.4932(12) 0.0379(19) 0.7383(16) 0.081(5) Uani 0.47(4) 1 d . U P A 1
H2C H 0.519(3) 0.073(6) 0.765(4) 0.098 Uiso 0.47(4) 1 d . U P A 1
H2D H 0.516(3) -0.054(6) 0.749(4) 0.098 Uiso 0.47(4) 1 d . U P A 1
O2' O 0.4831(8) 0.011(2) 0.7715(14) 0.083(4) Uani 0.53(4) 1 d . U P A 2
H2E H 0.519(3) 0.073(6) 0.765(4) 0.099 Uiso 0.53(4) 1 d . U P A 2
H2F H 0.516(3) -0.054(6) 0.749(4) 0.099 Uiso 0.53(4) 1 d . U P A 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N6 2.170(2) . ?
Zn1 N5 2.1824(19) . ?
Zn1 N1 2.221(2) . ?
Zn1 N3 2.2442(19) . ?
Zn1 N2 2.322(2) . ?
Zn1 N4 2.331(2) . ?
F1 B1 1.403(4) . ?
F2 B1 1.430(4) . ?
F3 B1 1.409(3) . ?
F4 B2 1.404(3) . ?
F5 B2 1.404(3) . ?
F6 B2 1.444(3) . ?
N1 C9 1.477(3) . ?
N1 C1 1.477(3) . ?
N1 C8 1.485(3) . ?
N2 C2 1.480(3) . ?
N2 C3 1.485(3) . ?
N2 C15 1.497(3) . ?
N3 C16 1.474(3) . ?
N3 C5 1.482(3) . ?
N3 C4 1.482(3) . ?
N4 C6 1.484(3) . ?
N4 C7 1.485(3) . ?
N4 C22 1.497(3) . ?
N5 C10 1.338(3) . ?
N5 C14 1.342(3) . ?
N6 C17 1.339(3) . ?
N6 C21 1.345(3) . ?
C1 C2 1.523(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.508(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.517(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.509(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.504(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.389(3) . ?
C11 C12 1.379(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 B1 1.619(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.508(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.385(3) . ?
C18 C19 1.379(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.372(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 B2 1.611(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
O1 H1C 0.76(5) . ?
O1 H1D 0.87(5) . ?
O2 H2C 0.70(6) . ?
O2 H2D 0.93(5) . ?
O2' H2E 0.84(6) . ?
O2' H2F 0.89(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N6 Zn1 N5 87.48(7) . . ?
N6 Zn1 N1 153.69(7) . . ?
N5 Zn1 N1 76.17(7) . . ?
N6 Zn1 N3 75.95(7) . . ?
N5 Zn1 N3 153.06(7) . . ?
N1 Zn1 N3 126.26(7) . . ?
N6 Zn1 N2 94.24(8) . . ?
N5 Zn1 N2 122.85(7) . . ?
N1 Zn1 N2 78.19(8) . . ?
N3 Zn1 N2 80.08(7) . . ?
N6 Zn1 N4 122.45(7) . . ?
N5 Zn1 N4 94.38(7) . . ?
N1 Zn1 N4 79.86(7) . . ?
N3 Zn1 N4 77.53(7) . . ?
N2 Zn1 N4 129.65(7) . . ?
C9 N1 C1 111.62(19) . . ?
C9 N1 C8 109.33(19) . . ?
C1 N1 C8 110.33(18) . . ?
C9 N1 Zn1 107.39(14) . . ?
C1 N1 Zn1 108.97(14) . . ?
C8 N1 Zn1 109.13(14) . . ?
C2 N2 C3 108.8(2) . . ?
C2 N2 C15 110.18(19) . . ?
C3 N2 C15 109.47(19) . . ?
C2 N2 Zn1 108.73(15) . . ?
C3 N2 Zn1 102.08(15) . . ?
C15 N2 Zn1 117.09(16) . . ?
C16 N3 C5 111.8(2) . . ?
C16 N3 C4 110.0(2) . . ?
C5 N3 C4 110.9(2) . . ?
C16 N3 Zn1 106.98(14) . . ?
C5 N3 Zn1 108.89(13) . . ?
C4 N3 Zn1 108.12(14) . . ?
C6 N4 C7 108.63(18) . . ?
C6 N4 C22 109.69(19) . . ?
C7 N4 C22 109.58(18) . . ?
C6 N4 Zn1 109.21(14) . . ?
C7 N4 Zn1 102.17(13) . . ?
C22 N4 Zn1 117.09(14) . . ?
C10 N5 C14 118.2(2) . . ?
C10 N5 Zn1 115.45(15) . . ?
C14 N5 Zn1 126.08(17) . . ?
C17 N6 C21 118.0(2) . . ?
C17 N6 Zn1 116.03(16) . . ?
C21 N6 Zn1 125.71(17) . . ?
N1 C1 C2 111.01(19) . . ?
N1 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
N1 C1 H1B 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
N2 C2 C1 111.5(2) . . ?
N2 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N2 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
N2 C3 C4 111.8(2) . . ?
N2 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
N2 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
N3 C4 C3 110.7(2) . . ?
N3 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N3 C5 C6 110.9(2) . . ?
N3 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N4 C6 C5 111.4(2) . . ?
N4 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
N4 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
N4 C7 C8 111.54(19) . . ?
N4 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
N4 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
N1 C8 C7 110.40(19) . . ?
N1 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
N1 C9 C10 110.16(19) . . ?
N1 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N1 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N5 C10 C11 122.2(2) . . ?
N5 C10 C9 116.2(2) . . ?
C11 C10 C9 121.6(2) . . ?
C12 C11 C10 118.9(3) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 119.4(2) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 118.1(3) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
N5 C14 C13 123.1(2) . . ?
N5 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?
N2 C15 B1 117.4(2) . . ?
N2 C15 H15A 108.0 . . ?
B1 C15 H15A 108.0 . . ?
N2 C15 H15B 108.0 . . ?
B1 C15 H15B 108.0 . . ?
H15A C15 H15B 107.2 . . ?
N3 C16 C17 110.2(2) . . ?
N3 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
N3 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
N6 C17 C18 122.2(2) . . ?
N6 C17 C16 116.3(2) . . ?
C18 C17 C16 121.6(2) . . ?
C19 C18 C17 119.2(2) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 118.9(2) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C21 C20 C19 118.5(2) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
N6 C21 C20 123.2(2) . . ?
N6 C21 H21 118.4 . . ?
C20 C21 H21 118.4 . . ?
N4 C22 B2 117.7(2) . . ?
N4 C22 H22A 107.9 . . ?
B2 C22 H22A 107.9 . . ?
N4 C22 H22B 107.9 . . ?
B2 C22 H22B 107.9 . . ?
H22A C22 H22B 107.2 . . ?
F1 B1 F3 107.9(2) . . ?
F1 B1 F2 106.6(2) . . ?
F3 B1 F2 106.9(2) . . ?
F1 B1 C15 110.0(2) . . ?
F3 B1 C15 112.9(2) . . ?
F2 B1 C15 112.2(2) . . ?
F5 B2 F4 108.7(2) . . ?
F5 B2 F6 106.2(2) . . ?
F4 B2 F6 106.3(2) . . ?
F5 B2 C22 110.2(2) . . ?
F4 B2 C22 113.2(2) . . ?
F6 B2 C22 111.8(2) . . ?
H1C O1 H1D 103(5) . . ?
H2C O2 H2D 91(6) . . ?
H2E O2' H2F 86(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
C9 N1 C1 C2 72.8(2) . . . . ?
C8 N1 C1 C2 -165.45(19) . . . . ?
Zn1 N1 C1 C2 -45.7(2) . . . . ?
C3 N2 C2 C1 79.5(2) . . . . ?
C15 N2 C2 C1 -160.5(2) . . . . ?
Zn1 N2 C2 C1 -30.9(2) . . . . ?
N1 C1 C2 N2 52.5(3) . . . . ?
C2 N2 C3 C4 -163.2(2) . . . . ?
C15 N2 C3 C4 76.4(3) . . . . ?
Zn1 N2 C3 C4 -48.4(2) . . . . ?
C16 N3 C4 C3 -152.7(2) . . . . ?
C5 N3 C4 C3 83.1(2) . . . . ?
Zn1 N3 C4 C3 -36.2(2) . . . . ?
N2 C3 C4 N3 60.8(3) . . . . ?
C16 N3 C5 C6 71.7(3) . . . . ?
C4 N3 C5 C6 -165.1(2) . . . . ?
Zn1 N3 C5 C6 -46.2(3) . . . . ?
C7 N4 C6 C5 79.5(2) . . . . ?
C22 N4 C6 C5 -160.7(2) . . . . ?
Zn1 N4 C6 C5 -31.2(2) . . . . ?
N3 C5 C6 N4 52.9(3) . . . . ?
C6 N4 C7 C8 -163.5(2) . . . . ?
C22 N4 C7 C8 76.7(2) . . . . ?
Zn1 N4 C7 C8 -48.2(2) . . . . ?
C9 N1 C8 C7 -153.1(2) . . . . ?
C1 N1 C8 C7 83.8(2) . . . . ?
Zn1 N1 C8 C7 -35.9(2) . . . . ?
N4 C7 C8 N1 60.1(3) . . . . ?
C1 N1 C9 C10 -160.73(19) . . . . ?
C8 N1 C9 C10 76.9(2) . . . . ?
Zn1 N1 C9 C10 -41.4(2) . . . . ?
C14 N5 C10 C11 -1.1(3) . . . . ?
Zn1 N5 C10 C11 173.53(16) . . . . ?
C14 N5 C10 C9 177.5(2) . . . . ?
Zn1 N5 C10 C9 -7.8(3) . . . . ?
N1 C9 C10 N5 34.0(3) . . . . ?
N1 C9 C10 C11 -147.4(2) . . . . ?
N5 C10 C11 C12 1.2(3) . . . . ?
C9 C10 C11 C12 -177.4(2) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C14 -1.3(4) . . . . ?
C10 N5 C14 C13 -0.3(4) . . . . ?
Zn1 N5 C14 C13 -174.26(18) . . . . ?
C12 C13 C14 N5 1.5(4) . . . . ?
C2 N2 C15 B1 52.9(3) . . . . ?
C3 N2 C15 B1 172.5(2) . . . . ?
Zn1 N2 C15 B1 -72.0(3) . . . . ?
C5 N3 C16 C17 -160.2(2) . . . . ?
C4 N3 C16 C17 76.1(2) . . . . ?
Zn1 N3 C16 C17 -41.1(2) . . . . ?
C21 N6 C17 C18 -0.9(4) . . . . ?
Zn1 N6 C17 C18 173.74(19) . . . . ?
C21 N6 C17 C16 178.8(2) . . . . ?
Zn1 N6 C17 C16 -6.6(3) . . . . ?
N3 C16 C17 N6 33.3(3) . . . . ?
N3 C16 C17 C18 -147.0(2) . . . . ?
N6 C17 C18 C19 0.9(4) . . . . ?
C16 C17 C18 C19 -178.8(2) . . . . ?
C17 C18 C19 C20 0.3(4) . . . . ?
C18 C19 C20 C21 -1.3(4) . . . . ?
C17 N6 C21 C20 -0.2(4) . . . . ?
Zn1 N6 C21 C20 -174.31(19) . . . . ?
C19 C20 C21 N6 1.3(4) . . . . ?
C6 N4 C22 B2 52.3(3) . . . . ?
C7 N4 C22 B2 171.5(2) . . . . ?
Zn1 N4 C22 B2 -72.8(2) . . . . ?
N2 C15 B1 F1 152.4(2) . . . . ?
N2 C15 B1 F3 31.8(4) . . . . ?
N2 C15 B1 F2 -89.1(3) . . . . ?
N4 C22 B2 F5 154.2(2) . . . . ?
N4 C22 B2 F4 32.3(3) . . . . ?
N4 C22 B2 F6 -87.8(3) . . . . ?

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.045





#===END
