# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2192088'
loop_
_audit_author_name
_audit_author_address
'Yaoguo Shen'
;Minjiang University
China
;
_audit_update_record             
;
2022-07-22 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_audit_creation_date             2022-07-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F6 Si, H2 O, 2(C3 H7 N6)'
_chemical_formula_sum            'C6 H16 F6 N12 O Si'
_chemical_formula_weight         414.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.7315(3)
_cell_length_b                   10.8592(3)
_cell_length_c                   17.9424(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.245(3)
_cell_angle_gamma                90
_cell_volume                     1506.05(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6650
_cell_measurement_temperature    297.14(10)
_cell_measurement_theta_max      29.4300
_cell_measurement_theta_min      2.1850
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?EID
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.828
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.793
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10674
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.793
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.331
_diffrn_reflns_theta_min         2.192
_diffrn_ambient_temperature      297.14(10)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.793
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2676
_reflns_number_total             3275
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3275
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0627P)²+0.6477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1205
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
2. Restrained distances
 H1C-O1 = O1-H1D
 0.9 with sigma of 0.02
 N6-F6_$1
 2.75 with sigma of 0.001
 N6-H6
 0.8 with sigma of 0.01
 H1C-H1D
 1.47 with sigma of 0.04
3.a X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N3(H3A,H3B), N5(H5A,H5B), N7(H7A,H7B), N9(H9A,H9B), N11(H11A,H11B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.53421(6) 0.49758(4) 0.75814(3) 0.02715(16) Uani 1 1 d . . . . .
F1 F 0.43064(19) 0.37252(11) 0.78907(9) 0.0580(4) Uani 1 1 d . . . . .
F2 F 0.5378(2) 0.43508(14) 0.67323(8) 0.0624(4) Uani 1 1 d . . . . .
F3 F 0.34259(16) 0.56316(11) 0.73848(8) 0.0502(4) Uani 1 1 d . . . . .
F4 F 0.63406(19) 0.62379(13) 0.72837(8) 0.0599(4) Uani 1 1 d . . . . .
F5 F 0.5317(2) 0.55632(12) 0.84452(7) 0.0539(4) Uani 1 1 d . . . . .
F6 F 0.72371(16) 0.43117(14) 0.77742(9) 0.0649(5) Uani 1 1 d . . . . .
O1 O 0.1204(2) 0.32129(15) 0.71950(10) 0.0523(5) Uani 1 1 d D . . . .
H1C H 0.216(3) 0.345(3) 0.7410(16) 0.075(10) Uiso 1 1 d D . . . .
H1D H 0.117(4) 0.2425(16) 0.7263(18) 0.093(11) Uiso 1 1 d D . . . .
N1 N 0.4333(2) -0.23865(14) 0.59754(9) 0.0363(4) Uani 1 1 d . . . . .
H1A H 0.382392 -0.291305 0.568756 0.044 Uiso 1 1 calc R U . . .
H1B H 0.503442 -0.263413 0.632241 0.044 Uiso 1 1 calc R U . . .
N2 N 0.2959(2) -0.08014(13) 0.53530(9) 0.0279(3) Uani 1 1 d . . . . .
N3 N 0.1744(2) 0.08660(14) 0.47605(9) 0.0323(4) Uani 1 1 d . . . . .
H3A H 0.160345 0.164674 0.470634 0.039 Uiso 1 1 calc R U . . .
H3B H 0.121950 0.036228 0.446292 0.039 Uiso 1 1 calc R U . . .
N4 N 0.3546(2) 0.12823(13) 0.57454(8) 0.0266(3) Uani 1 1 d . . . . .
N5 N 0.5483(2) 0.15899(14) 0.67162(9) 0.0331(4) Uani 1 1 d . . . . .
H5A H 0.534805 0.237363 0.667848 0.040 Uiso 1 1 calc R U . . .
H5B H 0.618029 0.129225 0.705004 0.040 Uiso 1 1 calc R U . . .
N6 N 0.48677(17) -0.03888(14) 0.63347(8) 0.0303(4) Uani 1 1 d D . . . .
H6 H 0.558(2) -0.0602(18) 0.6629(9) 0.026(5) Uiso 1 1 d D . . . .
C1 C 0.4036(2) -0.11957(16) 0.58845(10) 0.0273(4) Uani 1 1 d . . . . .
C2 C 0.2767(2) 0.04405(15) 0.53010(10) 0.0250(4) Uani 1 1 d . . . . .
C3 C 0.4625(2) 0.08469(16) 0.62634(10) 0.0252(4) Uani 1 1 d . . . . .
N7 N 0.8716(2) 0.25637(13) 0.56925(9) 0.0362(4) Uani 1 1 d . . . . .
H7A H 0.818150 0.208401 0.538341 0.043 Uiso 1 1 calc R U . . .
H7B H 0.935378 0.225789 0.604485 0.043 Uiso 1 1 calc R U . . .
N8 N 0.9457(2) 0.44791(13) 0.61222(9) 0.0273(3) Uani 1 1 d . . . . .
H8 H 1.007(3) 0.410(2) 0.6483(14) 0.045(6) Uiso 1 1 d . . . . .
N9 N 1.0303(2) 0.63692(15) 0.65493(9) 0.0346(4) Uani 1 1 d . . . . .
H9A H 1.029154 0.716057 0.653062 0.041 Uiso 1 1 calc R U . . .
H9B H 1.093756 0.599838 0.687874 0.041 Uiso 1 1 calc R U . . .
N10 N 0.83605(19) 0.62684(13) 0.55599(8) 0.0259(3) Uani 1 1 d . . . . .
N11 N 0.6574(2) 0.60196(14) 0.45520(9) 0.0340(4) Uani 1 1 d . . . . .
H11A H 0.651534 0.680886 0.452132 0.041 Uiso 1 1 calc R U . . .
H11B H 0.601364 0.556880 0.423516 0.041 Uiso 1 1 calc R U . . .
N12 N 0.75836(19) 0.42523(13) 0.50883(8) 0.0256(3) Uani 1 1 d . . . . .
C4 C 0.8558(2) 0.37651(15) 0.56262(10) 0.0252(4) Uani 1 1 d . . . . .
C5 C 0.9350(2) 0.57253(15) 0.60731(9) 0.0250(4) Uani 1 1 d . . . . .
C6 C 0.7518(2) 0.55027(15) 0.50827(10) 0.0248(4) Uani 1 1 d . . . . .


_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
Si1 F1 1.6771(13) . ?
Si1 F2 1.6686(14) . ?
Si1 F3 1.6745(12) . ?
Si1 F4 1.6666(13) . ?
Si1 F5 1.6766(13) . ?
Si1 F6 1.6626(12) . ?
O1 H1C 0.870(17) . ?
O1 H1D 0.865(17) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.323(2) . ?
N2 C1 1.323(2) . ?
N2 C2 1.360(2) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N3 C2 1.321(2) . ?
N4 C2 1.346(2) . ?
N4 C3 1.323(2) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N5 C3 1.314(2) . ?
N6 H6 0.791(9) . ?
N6 C1 1.346(2) . ?
N6 C3 1.360(2) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N7 C4 1.316(2) . ?
N8 H8 0.90(3) . ?
N8 C4 1.360(2) . ?
N8 C5 1.359(2) . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
N9 C5 1.317(2) . ?
N10 C5 1.323(2) . ?
N10 C6 1.351(2) . ?
N11 H11A 0.8600 . ?
N11 H11B 0.8600 . ?
N11 C6 1.313(2) . ?
N12 C4 1.322(2) . ?
N12 C6 1.359(2) . ?

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 Si1 F1 89.44(8) . . ?
F2 Si1 F3 90.74(8) . . ?
F2 Si1 F5 178.33(8) . . ?
F3 Si1 F1 89.28(7) . . ?
F3 Si1 F5 90.29(8) . . ?
F4 Si1 F1 178.75(8) . . ?
F4 Si1 F2 91.43(9) . . ?
F4 Si1 F3 89.81(7) . . ?
F4 Si1 F5 89.89(8) . . ?
F5 Si1 F1 89.25(8) . . ?
F6 Si1 F1 90.28(8) . . ?
F6 Si1 F2 88.94(8) . . ?
F6 Si1 F3 179.45(7) . . ?
F6 Si1 F4 90.64(8) . . ?
F6 Si1 F5 90.03(7) . . ?
H1C O1 H1D 105(3) . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
C1 N2 C2 115.87(15) . . ?
H3A N3 H3B 120.0 . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
C3 N4 C2 116.14(15) . . ?
H5A N5 H5B 120.0 . . ?
C3 N5 H5A 120.0 . . ?
C3 N5 H5B 120.0 . . ?
C1 N6 H6 121.9(15) . . ?
C1 N6 C3 121.51(14) . . ?
C3 N6 H6 116.4(15) . . ?
N1 C1 N2 120.66(17) . . ?
N1 C1 N6 118.88(17) . . ?
N2 C1 N6 120.45(16) . . ?
N3 C2 N2 117.38(16) . . ?
N3 C2 N4 116.74(16) . . ?
N4 C2 N2 125.87(16) . . ?
N4 C3 N6 120.14(15) . . ?
N5 C3 N4 121.13(16) . . ?
N5 C3 N6 118.73(16) . . ?
H7A N7 H7B 120.0 . . ?
C4 N7 H7A 120.0 . . ?
C4 N7 H7B 120.0 . . ?
C4 N8 H8 117.5(15) . . ?
C5 N8 H8 122.7(15) . . ?
C5 N8 C4 119.74(15) . . ?
H9A N9 H9B 120.0 . . ?
C5 N9 H9A 120.0 . . ?
C5 N9 H9B 120.0 . . ?
C5 N10 C6 115.50(15) . . ?
H11A N11 H11B 120.0 . . ?
C6 N11 H11A 120.0 . . ?
C6 N11 H11B 120.0 . . ?
C4 N12 C6 115.22(15) . . ?
N7 C4 N8 117.47(16) . . ?
N7 C4 N12 120.88(16) . . ?
N12 C4 N8 121.64(15) . . ?
N9 C5 N8 117.03(16) . . ?
N9 C5 N10 121.45(16) . . ?
N10 C5 N8 121.50(16) . . ?
N10 C6 N12 126.35(16) . . ?
N11 C6 N10 116.71(16) . . ?
N11 C6 N12 116.92(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1C F1 0.870(17) 1.874(18) 2.737(2) 171(3) . yes
N6 H6 F6 0.791(9) 1.979(11) 2.7418(9) 162(2) 2_646 yes
N7 H7B F5 0.86 2.07 2.761(2) 137.0 2_646 yes
N8 H8 O1 0.90(3) 1.81(3) 2.703(2) 176(2) 1_655 yes
N9 H9A F1 0.86 2.01 2.763(2) 145.3 2_656 yes
N11 H11B F2 0.86 2.02 2.756(2) 142.5 3_666 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N2 C2 N3 177.86(16) . . . . ?
C1 N2 C2 N4 -1.1(3) . . . . ?
C1 N6 C3 N4 0.3(3) . . . . ?
C1 N6 C3 N5 -179.53(17) . . . . ?
C2 N2 C1 N1 -179.06(17) . . . . ?
C2 N2 C1 N6 -0.1(3) . . . . ?
C2 N4 C3 N5 178.47(16) . . . . ?
C2 N4 C3 N6 -1.4(3) . . . . ?
C3 N4 C2 N2 1.9(3) . . . . ?
C3 N4 C2 N3 -177.12(16) . . . . ?
C3 N6 C1 N1 179.45(17) . . . . ?
C3 N6 C1 N2 0.5(3) . . . . ?
C4 N8 C5 N9 -177.29(16) . . . . ?
C4 N8 C5 N10 1.3(3) . . . . ?
C4 N12 C6 N10 1.1(3) . . . . ?
C4 N12 C6 N11 179.43(16) . . . . ?
C5 N8 C4 N7 179.39(17) . . . . ?
C5 N8 C4 N12 0.5(3) . . . . ?
C5 N10 C6 N11 -177.74(16) . . . . ?
C5 N10 C6 N12 0.6(3) . . . . ?
C6 N10 C5 N8 -1.8(2) . . . . ?
C6 N10 C5 N9 176.73(16) . . . . ?
C6 N12 C4 N7 179.59(17) . . . . ?
C6 N12 C4 N8 -1.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
