#------------------------------------------------------------------------------
#$Date: 2024-07-16 03:10:43 +0200 (Tue 16 de Jul de 2024) $
#$Revision: 293421 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/90/7249051.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7249051
loop_
_publ_author_name
'Trojan, Michal'
'Hroch, Adam'
'Gruden, Evelin'
'Cvačka, Josef'
'Čejka, Jan'
'Tavčar, Gašper'
'Rybáčková, Markéta'
'Kvíčala, Jaroslav'
_publ_section_title
;
 Modified aryldifluorophenylsilicates with improved activity and
 selectivity in nucleophilic fluorination of secondary substrates
;
_journal_issue                   31
_journal_name_full               'RSC Advances'
_journal_page_first              22326
_journal_page_last               22334
_journal_paper_doi               10.1039/D4RA04332D
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C36 H55 F2 N1 O2 Si1'
_chemical_formula_sum            'C36 H55 F2 N O2 Si'
_chemical_formula_weight         599.92
_chemical_name_common
'Butan-1-aminium, N,N,N-tributyl, (TB-5-11)-difluorobis(4-methoxyphenyl)phenylsilicate(1-)'
_chemical_name_systematic
'Tetrabutylammonium difluorobis(4-methoxyphenyl)phenylsilicate'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2023-12-07 deposited with the CCDC.	2024-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.3146(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4251(3)
_cell_length_b                   20.4233(7)
_cell_length_c                   18.7305(6)
_cell_measurement_reflns_used    9072
_cell_measurement_temperature    180
_cell_measurement_theta_max      74.51
_cell_measurement_theta_min      4.33
_cell_volume                     3508.6(2)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Apex4 (Bruker AXS, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex4'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.078
_diffrn_reflns_av_unetI/netI     0.142
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            55289
_diffrn_reflns_theta_full        68.243
_diffrn_reflns_theta_max         68.243
_diffrn_reflns_theta_min         3.250
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.914
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.544
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.074
_refine_diff_density_max         1.02
_refine_diff_density_min         -0.71
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0800
_refine_ls_shift/su_max          0.0003488
_refine_ls_shift/su_mean         0.0000212
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.11P)² + 4.31P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2311
_refine_ls_wR_factor_gt          0.2223
_refine_ls_wR_factor_ref         0.2311
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              24
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                5119
_reflns_number_total             6424
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   3.91
_oxford_diffrn_Wilson_scale      72.82
_oxford_refine_ls_scale          0.12648(10)
_cod_data_source_file            d4ra04332d2.cif
_cod_data_source_block           I_CCDC2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_original_formula_sum        'C36 H55 F2 N1 O2 Si1'
_cod_database_code               7249051
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_r_factor_ref          0.0915
_reflns_number_all               6424
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Si1 Si 0.36132(10) 0.69226(5) 0.37205(4) 0.0496 1.0000 Uani . . . . . .
F2 F 0.2704(2) 0.68661(10) 0.44259(9) 0.0546 1.0000 Uani . . . . . .
F3 F 0.4472(2) 0.69656(11) 0.30003(9) 0.0609 1.0000 Uani . . . . . .
C4 C 0.5259(3) 0.64808(16) 0.42918(15) 0.0445 1.0000 Uani . . . . . .
C5 C 0.6665(4) 0.65634(16) 0.41658(16) 0.0476 1.0000 Uani . . . . . .
C6 C 0.7859(3) 0.62310(16) 0.45479(17) 0.0459 1.0000 Uani . . . . . .
C7 C 0.7702(3) 0.57806(14) 0.50808(16) 0.0410 1.0000 Uani . . . . . .
C8 C 0.6352(3) 0.56851(15) 0.52307(15) 0.0420 1.0000 Uani . . . . . .
C9 C 0.5162(3) 0.60411(15) 0.48465(15) 0.0424 1.0000 Uani . . . . . .
C11 C 0.8806(4) 0.49016(18) 0.5852(2) 0.0614 1.0000 Uani . . . . . .
C12 C 0.3620(4) 0.78563(19) 0.37898(18) 0.0544 1.0000 Uani . . . . . .
C13 C 0.4767(4) 0.8224(2) 0.3651(2) 0.0635 1.0000 Uani . . . . . .
C14 C 0.4855(5) 0.8890(2) 0.3743(2) 0.0729 1.0000 Uani . . . . . .
C15 C 0.3762(6) 0.9226(2) 0.3949(2) 0.0801 1.0000 Uani . . . . . .
C16 C 0.2552(6) 0.8889(2) 0.4055(3) 0.0910 1.0000 Uani . . . . . .
C17 C 0.2522(5) 0.8211(2) 0.3985(2) 0.0740 1.0000 Uani . . . . . .
C19 C 0.5087(9) 1.0227(3) 0.4094(4) 0.1228 1.0000 Uani . . . . . .
C20 C 0.2020(4) 0.64595(18) 0.31022(17) 0.0552 1.0000 Uani . . . . . .
C21 C 0.0578(4) 0.65339(19) 0.3163(2) 0.0603 1.0000 Uani . . . . . .
C22 C -0.0579(5) 0.6206(2) 0.2707(2) 0.0755 1.0000 Uani . . . . . .
C23 C -0.0343(6) 0.5762(3) 0.2187(3) 0.0840 1.0000 Uani . . . . . .
C24 C 0.1068(6) 0.5672(2) 0.2122(2) 0.0812 1.0000 Uani . . . . . .
C25 C 0.2220(5) 0.60188(19) 0.25594(19) 0.0633 1.0000 Uani . . . . . .
C27 C 0.0814(3) 0.78891(17) 0.18677(16) 0.0450 1.0000 Uani . . . . . .
C28 C -0.0515(3) 0.83304(18) 0.17662(18) 0.0522 1.0000 Uani . . . . . .
C29 C -0.1272(4) 0.8242(2) 0.2391(2) 0.0615 1.0000 Uani . . . . . .
C30 C -0.2573(5) 0.8691(2) 0.2328(3) 0.0787 1.0000 Uani . . . . . .
C31 C 0.0689(3) 0.76010(19) 0.05526(16) 0.0520 1.0000 Uani . . . . . .
C32 C 0.0352(4) 0.6879(2) 0.0573(2) 0.0589 1.0000 Uani . . . . . .
C33 C -0.0743(4) 0.6664(2) -0.0124(2) 0.0723 1.0000 Uani . . . . . .
C34 C -0.1055(6) 0.5934(3) -0.0129(3) 0.1005 1.0000 Uani . . . . . .
C35 C 0.3002(3) 0.75028(16) 0.15288(16) 0.0441 1.0000 Uani . . . . . .
C36 C 0.4012(3) 0.74541(19) 0.10065(18) 0.0536 1.0000 Uani . . . . . .
C37 C 0.5355(4) 0.7069(2) 0.1367(2) 0.0574 1.0000 Uani . . . . . .
C38 C 0.6407(4) 0.7011(2) 0.0869(2) 0.0753 1.0000 Uani . . . . . .
C39 C 0.1985(3) 0.85940(17) 0.10668(17) 0.0486 1.0000 Uani . . . . . .
C40 C 0.2902(4) 0.89770(18) 0.16864(19) 0.0558 1.0000 Uani . . . . . .
C41 C 0.3160(4) 0.96666(19) 0.1435(2) 0.0646 1.0000 Uani . . . . . .
C42 C 0.4049(5) 1.0078(2) 0.2035(3) 0.0818 1.0000 Uani . . . . . .
O10 O 0.8950(2) 0.54555(11) 0.54126(13) 0.0524 1.0000 Uani . . . . . .
O18 O 0.3738(5) 0.98822(18) 0.4052(2) 0.1167 1.0000 Uani . . . . . .
N26 N 0.1623(2) 0.78981(13) 0.12518(13) 0.0426 1.0000 Uani . . . . . .
H61 H 0.3509 0.7709 0.1981 0.0514 1.0000 Uiso R . . . . .
H62 H 0.2702 0.7071 0.1650 0.0529 1.0000 Uiso R . . . . .
H71 H 0.6801 0.6850 0.3796 0.0551 1.0000 Uiso R . . . . .
H91 H 0.4263 0.5963 0.4958 0.0481 1.0000 Uiso R . . . . .
H111 H 0.6214 0.5367 0.5582 0.0490 1.0000 Uiso R . . . . .
H121 H 0.8782 0.6308 0.4450 0.0522 1.0000 Uiso R . . . . .
H131 H 0.4281 0.7882 0.0886 0.0641 1.0000 Uiso R . . . . .
H132 H 0.3554 0.7226 0.0553 0.0648 1.0000 Uiso R . . . . .
H141 H 0.2524 0.8550 0.0685 0.0567 1.0000 Uiso R . . . . .
H142 H 0.1082 0.8814 0.0860 0.0570 1.0000 Uiso R . . . . .
H151 H -0.0238 0.7837 0.0453 0.0614 1.0000 Uiso R . . . . .
H152 H 0.1182 0.7684 0.0162 0.0617 1.0000 Uiso R . . . . .
H161 H 0.1503 0.8002 0.2316 0.0545 1.0000 Uiso R . . . . .
H162 H 0.0541 0.7445 0.1921 0.0540 1.0000 Uiso R . . . . .
H171 H 0.5846 0.7274 0.1832 0.0682 1.0000 Uiso R . . . . .
H172 H 0.5053 0.6623 0.1448 0.0680 1.0000 Uiso R . . . . .
H181 H 0.2419 0.9016 0.2094 0.0642 1.0000 Uiso R . . . . .
H182 H 0.3826 0.8759 0.1859 0.0648 1.0000 Uiso R . . . . .
H191 H -0.1196 0.8220 0.1320 0.0620 1.0000 Uiso R . . . . .
H192 H -0.0257 0.8790 0.1758 0.0631 1.0000 Uiso R . . . . .
H211 H -0.0588 0.8349 0.2840 0.0711 1.0000 Uiso R . . . . .
H212 H -0.1550 0.7792 0.2429 0.0713 1.0000 Uiso R . . . . .
H231 H -0.0034 0.6785 0.0993 0.0688 1.0000 Uiso R . . . . .
H232 H 0.1209 0.6621 0.0620 0.0691 1.0000 Uiso R . . . . .
H241 H 0.0421 0.6820 0.3530 0.0699 1.0000 Uiso R . . . . .
H251 H 0.9775 0.4709 0.6023 0.0916 1.0000 Uiso R . . . . .
H252 H 0.8447 0.5036 0.6277 0.0916 1.0000 Uiso R . . . . .
H253 H 0.8152 0.4577 0.5551 0.0920 1.0000 Uiso R . . . . .
H271 H 0.7281 0.6801 0.1129 0.1143 1.0000 Uiso R . . . . .
H272 H 0.5930 0.6760 0.0438 0.1152 1.0000 Uiso R . . . . .
H273 H 0.6623 0.7446 0.0725 0.1152 1.0000 Uiso R . . . . .
H281 H 0.5518 0.8002 0.3491 0.0730 1.0000 Uiso R . . . . .
H291 H 0.3651 0.9632 0.1029 0.0775 1.0000 Uiso R . . . . .
H292 H 0.2215 0.9880 0.1279 0.0775 1.0000 Uiso R . . . . .
H301 H 0.3165 0.5961 0.2495 0.0722 1.0000 Uiso R . . . . .
H311 H -0.1535 0.6294 0.2746 0.0884 1.0000 Uiso R . . . . .
H321 H -0.1110 0.5522 0.1867 0.0981 1.0000 Uiso R . . . . .
H331 H -0.1606 0.6913 -0.0168 0.0844 1.0000 Uiso R . . . . .
H332 H -0.0381 0.6779 -0.0545 0.0855 1.0000 Uiso R . . . . .
H341 H 0.1727 0.7972 0.4073 0.0875 1.0000 Uiso R . . . . .
H351 H 0.1265 0.5381 0.1767 0.0953 1.0000 Uiso R . . . . .
H361 H 0.5668 0.9111 0.3663 0.0823 1.0000 Uiso R . . . . .
H371 H 0.3624 1.0100 0.2454 0.1225 1.0000 Uiso R . . . . .
H372 H 0.4162 1.0512 0.1877 0.1220 1.0000 Uiso R . . . . .
H373 H 0.5006 0.9897 0.2185 0.1222 1.0000 Uiso R . . . . .
H381 H -0.2230 0.9129 0.2346 0.1181 1.0000 Uiso R . . . . .
H382 H -0.3011 0.8614 0.2736 0.1178 1.0000 Uiso R . . . . .
H383 H -0.3257 0.8619 0.1869 0.1180 1.0000 Uiso R . . . . .
H401 H -0.1514 0.5819 0.0272 0.1528 1.0000 Uiso R . . . . .
H402 H -0.1691 0.5816 -0.0595 0.1529 1.0000 Uiso R . . . . .
H403 H -0.0142 0.5701 -0.0067 0.1528 1.0000 Uiso R . . . . .
H411 H 0.1782 0.9114 0.4188 0.1012 1.0000 Uiso R . . . . .
H421 H 0.4959 1.0693 0.4215 0.1839 1.0000 Uiso R . . . . .
H422 H 0.5869 1.0022 0.4471 0.1847 1.0000 Uiso R . . . . .
H423 H 0.5390 1.0214 0.3622 0.1838 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Si 0.2541 0.3302 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937
1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F2 . Si1 . F3 . 178.14(11) yes
F2 . Si1 . C4 . 91.27(11) yes
F3 . Si1 . C4 . 89.73(11) yes
F2 . Si1 . C12 . 90.54(12) yes
F3 . Si1 . C12 . 90.42(13) yes
C4 . Si1 . C12 . 116.51(15) yes
F2 . Si1 . C20 . 88.38(12) yes
F3 . Si1 . C20 . 89.77(13) yes
C4 . Si1 . C20 . 122.00(15) yes
C12 . Si1 . C20 . 121.49(15) yes
Si1 . C4 . C5 . 121.8(2) yes
Si1 . C4 . C9 . 122.8(2) yes
C5 . C4 . C9 . 115.4(3) yes
C4 . C5 . C6 . 123.1(3) yes
C4 . C5 . H71 . 119.5 no
C6 . C5 . H71 . 117.4 no
C5 . C6 . C7 . 119.6(3) yes
C5 . C6 . H121 . 120.1 no
C7 . C6 . H121 . 120.3 no
C6 . C7 . C8 . 119.7(3) yes
C6 . C7 . O10 . 115.1(3) yes
C8 . C7 . O10 . 125.2(3) yes
C7 . C8 . C9 . 119.5(3) yes
C7 . C8 . H111 . 121.0 no
C9 . C8 . H111 . 119.4 no
C4 . C9 . C8 . 122.7(3) yes
C4 . C9 . H91 . 119.8 no
C8 . C9 . H91 . 117.5 no
O10 . C11 . H251 . 107.6 no
O10 . C11 . H252 . 110.2 no
H251 . C11 . H252 . 108.6 no
O10 . C11 . H253 . 109.5 no
H251 . C11 . H253 . 109.2 no
H252 . C11 . H253 . 111.5 no
Si1 . C12 . C13 . 121.2(3) yes
Si1 . C12 . C17 . 123.4(3) yes
C13 . C12 . C17 . 115.4(4) yes
C12 . C13 . C14 . 122.7(4) yes
C12 . C13 . H281 . 118.2 no
C14 . C13 . H281 . 119.1 no
C13 . C14 . C15 . 120.5(4) yes
C13 . C14 . H361 . 119.3 no
C15 . C14 . H361 . 120.3 no
C14 . C15 . C16 . 119.4(4) yes
C14 . C15 . O18 . 125.2(5) yes
C16 . C15 . O18 . 115.5(5) yes
C15 . C16 . C17 . 118.8(4) yes
C15 . C16 . H411 . 120.4 no
C17 . C16 . H411 . 120.8 no
C16 . C17 . C12 . 123.2(4) yes
C16 . C17 . H341 . 120.1 no
C12 . C17 . H341 . 116.7 no
O18 . C19 . H421 . 109.3 no
O18 . C19 . H422 . 109.6 no
H421 . C19 . H422 . 110.8 no
O18 . C19 . H423 . 111.7 no
H421 . C19 . H423 . 107.6 no
H422 . C19 . H423 . 107.8 no
Si1 . C20 . C21 . 122.5(3) yes
Si1 . C20 . C25 . 122.4(3) yes
C21 . C20 . C25 . 115.1(4) yes
C20 . C21 . C22 . 122.5(4) yes
C20 . C21 . H241 . 116.5 no
C22 . C21 . H241 . 121.0 no
C21 . C22 . C23 . 121.0(4) yes
C21 . C22 . H311 . 119.5 no
C23 . C22 . H311 . 119.5 no
C22 . C23 . C24 . 117.7(5) yes
C22 . C23 . H321 . 123.5 no
C24 . C23 . H321 . 118.8 no
C23 . C24 . C25 . 121.2(4) yes
C23 . C24 . H351 . 120.0 no
C25 . C24 . H351 . 118.8 no
C20 . C25 . C24 . 122.4(4) yes
C20 . C25 . H301 . 117.7 no
C24 . C25 . H301 . 119.9 no
C28 . C27 . N26 . 116.1(2) yes
C28 . C27 . H161 . 109.8 no
N26 . C27 . H161 . 107.6 no
C28 . C27 . H162 . 110.0 no
N26 . C27 . H162 . 106.6 no
H161 . C27 . H162 . 106.3 no
C27 . C28 . C29 . 110.7(3) yes
C27 . C28 . H191 . 109.7 no
C29 . C28 . H191 . 107.9 no
C27 . C28 . H192 . 111.9 no
C29 . C28 . H192 . 107.0 no
H191 . C28 . H192 . 109.5 no
C28 . C29 . C30 . 112.6(3) yes
C28 . C29 . H211 . 108.0 no
C30 . C29 . H211 . 107.3 no
C28 . C29 . H212 . 110.9 no
C30 . C29 . H212 . 110.8 no
H211 . C29 . H212 . 107.0 no
C29 . C30 . H381 . 107.8 no
C29 . C30 . H382 . 109.1 no
H381 . C30 . H382 . 109.4 no
C29 . C30 . H383 . 109.9 no
H381 . C30 . H383 . 109.2 no
H382 . C30 . H383 . 111.4 no
C32 . C31 . N26 . 116.7(3) yes
C32 . C31 . H151 . 107.6 no
N26 . C31 . H151 . 106.3 no
C32 . C31 . H152 . 109.3 no
N26 . C31 . H152 . 107.3 no
H151 . C31 . H152 . 109.4 no
C31 . C32 . C33 . 111.3(3) yes
C31 . C32 . H231 . 109.7 no
C33 . C32 . H231 . 109.4 no
C31 . C32 . H232 . 111.3 no
C33 . C32 . H232 . 108.2 no
H231 . C32 . H232 . 106.8 no
C32 . C33 . C34 . 112.2(4) yes
C32 . C33 . H331 . 108.5 no
C34 . C33 . H331 . 111.5 no
C32 . C33 . H332 . 109.5 no
C34 . C33 . H332 . 109.9 no
H331 . C33 . H332 . 104.9 no
C33 . C34 . H401 . 110.4 no
C33 . C34 . H402 . 109.1 no
H401 . C34 . H402 . 110.0 no
C33 . C34 . H403 . 108.5 no
H401 . C34 . H403 . 109.2 no
H402 . C34 . H403 . 109.6 no
C36 . C35 . N26 . 115.5(2) yes
C36 . C35 . H61 . 109.6 no
N26 . C35 . H61 . 106.2 no
C36 . C35 . H62 . 110.6 no
N26 . C35 . H62 . 107.0 no
H61 . C35 . H62 . 107.7 no
C35 . C36 . C37 . 109.4(3) yes
C35 . C36 . H131 . 109.5 no
C37 . C36 . H131 . 110.0 no
C35 . C36 . H132 . 112.0 no
C37 . C36 . H132 . 107.3 no
H131 . C36 . H132 . 108.7 no
C36 . C37 . C38 . 111.5(3) yes
C36 . C37 . H171 . 110.5 no
C38 . C37 . H171 . 109.8 no
C36 . C37 . H172 . 108.1 no
C38 . C37 . H172 . 106.1 no
H171 . C37 . H172 . 110.8 no
C37 . C38 . H271 . 109.4 no
C37 . C38 . H272 . 108.0 no
H271 . C38 . H272 . 111.4 no
C37 . C38 . H273 . 108.1 no
H271 . C38 . H273 . 110.1 no
H272 . C38 . H273 . 109.8 no
C40 . C39 . N26 . 115.6(2) yes
C40 . C39 . H141 . 108.2 no
N26 . C39 . H141 . 105.3 no
C40 . C39 . H142 . 111.5 no
N26 . C39 . H142 . 107.8 no
H141 . C39 . H142 . 108.1 no
C39 . C40 . C41 . 110.4(3) yes
C39 . C40 . H181 . 110.9 no
C41 . C40 . H181 . 107.6 no
C39 . C40 . H182 . 109.5 no
C41 . C40 . H182 . 109.5 no
H181 . C40 . H182 . 108.8 no
C40 . C41 . C42 . 112.9(3) yes
C40 . C41 . H291 . 108.1 no
C42 . C41 . H291 . 110.0 no
C40 . C41 . H292 . 107.8 no
C42 . C41 . H292 . 106.9 no
H291 . C41 . H292 . 111.2 no
C41 . C42 . H371 . 111.9 no
C41 . C42 . H372 . 112.0 no
H371 . C42 . H372 . 108.0 no
C41 . C42 . H373 . 109.4 no
H371 . C42 . H373 . 108.7 no
H372 . C42 . H373 . 106.6 no
C11 . O10 . C7 . 117.5(2) yes
C19 . O18 . C15 . 116.6(5) yes
C31 . N26 . C27 . 110.8(2) yes
C31 . N26 . C39 . 106.9(2) yes
C27 . N26 . C39 . 111.2(2) yes
C31 . N26 . C35 . 111.2(2) yes
C27 . N26 . C35 . 105.9(2) yes
C39 . N26 . C35 . 110.9(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Si1 . F2 . 1.7365(18) yes
Si1 . F3 . 1.7277(19) yes
Si1 . C4 . 1.898(3) yes
Si1 . C12 . 1.911(4) yes
Si1 . C20 . 1.921(4) yes
C4 . C5 . 1.409(4) yes
C4 . C9 . 1.392(4) yes
C5 . C6 . 1.367(4) yes
C5 . H71 . 0.937 no
C6 . C7 . 1.390(4) yes
C6 . H121 . 0.941 no
C7 . C8 . 1.379(4) yes
C7 . O10 . 1.369(4) yes
C8 . C9 . 1.390(4) yes
C8 . H111 . 0.954 no
C9 . H91 . 0.932 no
C11 . O10 . 1.424(4) yes
C11 . H251 . 0.978 no
C11 . H252 . 0.973 no
C11 . H253 . 0.989 no
C12 . C13 . 1.389(5) yes
C12 . C17 . 1.381(5) yes
C13 . C14 . 1.371(6) yes
C13 . H281 . 0.945 no
C14 . C15 . 1.364(6) yes
C14 . H361 . 0.932 no
C15 . C16 . 1.385(7) yes
C15 . O18 . 1.356(6) yes
C16 . C17 . 1.389(7) yes
C16 . H411 . 0.940 no
C17 . H341 . 0.940 no
C19 . O18 . 1.439(8) yes
C19 . H421 . 0.992 no
C19 . H422 . 0.988 no
C19 . H423 . 0.990 no
C20 . C21 . 1.398(5) yes
C20 . C25 . 1.403(5) yes
C21 . C22 . 1.391(6) yes
C21 . H241 . 0.939 no
C22 . C23 . 1.388(7) yes
C22 . H311 . 0.937 no
C23 . C24 . 1.375(7) yes
C23 . H321 . 0.960 no
C24 . C25 . 1.395(6) yes
C24 . H351 . 0.941 no
C25 . H301 . 0.933 no
C27 . C28 . 1.519(4) yes
C27 . N26 . 1.522(3) yes
C27 . H161 . 0.963 no
C27 . H162 . 0.954 no
C28 . C29 . 1.515(4) yes
C28 . H191 . 0.957 no
C28 . H192 . 0.970 no
C29 . C30 . 1.515(5) yes
C29 . H211 . 0.959 no
C29 . H212 . 0.963 no
C30 . H381 . 0.948 no
C30 . H382 . 0.961 no
C30 . H383 . 0.960 no
C31 . C32 . 1.511(5) yes
C31 . N26 . 1.525(4) yes
C31 . H151 . 0.978 no
C31 . H152 . 0.968 no
C32 . C33 . 1.530(5) yes
C32 . H231 . 0.959 no
C32 . H232 . 0.950 no
C33 . C34 . 1.520(7) yes
C33 . H331 . 0.947 no
C33 . H332 . 0.958 no
C34 . H401 . 0.979 no
C34 . H402 . 0.969 no
C34 . H403 . 0.966 no
C35 . C36 . 1.517(4) yes
C35 . N26 . 1.516(3) yes
C35 . H61 . 0.969 no
C35 . H62 . 0.969 no
C36 . C37 . 1.511(4) yes
C36 . H131 . 0.951 no
C36 . H132 . 0.978 no
C37 . C38 . 1.514(5) yes
C37 . H171 . 0.981 no
C37 . H172 . 0.978 no
C38 . H271 . 0.956 no
C38 . H272 . 0.975 no
C38 . H273 . 0.964 no
C39 . C40 . 1.498(5) yes
C39 . N26 . 1.520(4) yes
C39 . H141 . 0.971 no
C39 . H142 . 0.962 no
C40 . C41 . 1.522(5) yes
C40 . H181 . 0.978 no
C40 . H182 . 0.965 no
C41 . C42 . 1.495(6) yes
C41 . H291 . 0.980 no
C41 . H292 . 0.974 no
C42 . H371 . 0.962 no
C42 . H372 . 0.949 no
C42 . H373 . 0.955 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C39 . H142 . O10 4_464 171 0.96 2.49 3.440(6) yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_site_symmetry_1
_geom_torsion_atom_site_label_2
_geom_torsion_site_symmetry_2
_geom_torsion_atom_site_label_3
_geom_torsion_site_symmetry_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
F2 . Si1 . C4 . C5 . -155.3(6) yes
F2 . Si1 . C4 . C9 . 26.6(7) yes
F3 . Si1 . C4 . C5 . 26.2(7) yes
F3 . Si1 . C4 . C9 . -151.9(6) yes
C12 . Si1 . C4 . C5 . -64.1(7) yes
C12 . Si1 . C4 . C9 . 117.8(7) yes
C20 . Si1 . C4 . C5 . 115.8(7) yes
C20 . Si1 . C4 . C9 . -62.3(7) yes
F2 . Si1 . C12 . C13 . 146.7(8) yes
F2 . Si1 . C12 . C17 . -32.6(9) yes
F3 . Si1 . C12 . C13 . -34.9(8) yes
F3 . Si1 . C12 . C17 . 145.8(9) yes
C4 . Si1 . C12 . C13 . 55.0(9) yes
C4 . Si1 . C12 . C17 . -124.3(8) yes
C20 . Si1 . C12 . C13 . -124.9(8) yes
C20 . Si1 . C12 . C17 . 55.9(10) yes
F2 . Si1 . C20 . C21 . 34.0(7) yes
F2 . Si1 . C20 . C25 . -145.6(7) yes
F3 . Si1 . C20 . C21 . -146.0(7) yes
F3 . Si1 . C20 . C25 . 34.4(7) yes
C4 . Si1 . C20 . C21 . 124.5(6) yes
C4 . Si1 . C20 . C25 . -55.1(8) yes
C12 . Si1 . C20 . C21 . -55.6(8) yes
C12 . Si1 . C20 . C25 . 124.8(7) yes
Si1 . C4 . C5 . C6 . -177.2(5) yes
Si1 . C4 . C5 . H71 . 1.1 no
C9 . C4 . C5 . C6 . 1.0(8) yes
C9 . C4 . C5 . H71 . 179.4 no
Si1 . C4 . C9 . C8 . 175.5(4) yes
Si1 . C4 . C9 . H91 . -1.7 no
C5 . C4 . C9 . C8 . -2.7(8) yes
C5 . C4 . C9 . H91 . -179.9 no
C4 . C5 . C6 . C7 . 1.0(8) yes
C4 . C5 . C6 . H121 . -178.9 no
H71 . C5 . C6 . C7 . -177.3 no
H71 . C5 . C6 . H121 . 2.7 no
C5 . C6 . C7 . C8 . -1.5(8) yes
C5 . C6 . C7 . O10 . 177.6(5) yes
H121 . C6 . C7 . C8 . 178.4 no
H121 . C6 . C7 . O10 . -2.4 no
C6 . C7 . C8 . C9 . -0.0(8) yes
C6 . C7 . C8 . H111 . 177.8 no
O10 . C7 . C8 . C9 . -179.1(4) yes
O10 . C7 . C8 . H111 . -1.3 no
C6 . C7 . O10 . C11 . -167.8(5) yes
C8 . C7 . O10 . C11 . 11.3(7) yes
C7 . C8 . C9 . C4 . 2.2(8) yes
C7 . C8 . C9 . H91 . 179.5 no
H111 . C8 . C9 . C4 . -175.6 no
H111 . C8 . C9 . H91 . 1.7 no
H251 . C11 . O10 . C7 . 176.5 no
H252 . C11 . O10 . C7 . -65.2 no
H253 . C11 . O10 . C7 . 57.9 no
Si1 . C12 . C13 . C14 . -175.5(6) yes
Si1 . C12 . C13 . H281 . 3.9 no
C17 . C12 . C13 . C14 . 3.8(11) yes
C17 . C12 . C13 . H281 . -176.7 no
Si1 . C12 . C17 . C16 . 178.1(7) yes
Si1 . C12 . C17 . H341 . -1.7 no
C13 . C12 . C17 . C16 . -1.2(12) yes
C13 . C12 . C17 . H341 . 179.0 no
C12 . C13 . C14 . C15 . -2.9(12) yes
C12 . C13 . C14 . H361 . 177.2 no
H281 . C13 . C14 . C15 . 177.6 no
H281 . C13 . C14 . H361 . -2.2 no
C13 . C14 . C15 . C16 . -0.8(13) yes
C13 . C14 . C15 . O18 . -179.7(8) yes
H361 . C14 . C15 . C16 . 179.0 no
H361 . C14 . C15 . O18 . 0.1 no
C14 . C15 . C16 . C17 . 3.3(15) yes
C14 . C15 . C16 . H411 . -178.9 no
O18 . C15 . C16 . C17 . -177.7(9) yes
O18 . C15 . C16 . H411 . 0.1 no
C14 . C15 . O18 . C19 . -13.4(14) yes
C16 . C15 . O18 . C19 . 167.7(10) yes
C15 . C16 . C17 . C12 . -2.2(15) yes
C15 . C16 . C17 . H341 . 177.5 no
H411 . C16 . C17 . C12 . 179.9 no
H411 . C16 . C17 . H341 . -0.3 no
H421 . C19 . O18 . C15 . -174.9 no
H422 . C19 . O18 . C15 . -53.3 no
H423 . C19 . O18 . C15 . 66.1 no
Si1 . C20 . C21 . C22 . 179.0(5) yes
Si1 . C20 . C21 . H241 . -1.0 no
C25 . C20 . C21 . C22 . -1.4(9) yes
C25 . C20 . C21 . H241 . 178.7 no
Si1 . C20 . C25 . C24 . 178.5(5) yes
Si1 . C20 . C25 . H301 . -1.5 no
C21 . C20 . C25 . C24 . -1.1(9) yes
C21 . C20 . C25 . H301 . 178.9 no
C20 . C21 . C22 . C23 . 3.0(10) yes
C20 . C21 . C22 . H311 . -175.7 no
H241 . C21 . C22 . C23 . -177.1 no
H241 . C21 . C22 . H311 . 4.2 no
C21 . C22 . C23 . C24 . -1.9(11) yes
C21 . C22 . C23 . H321 . 179.1 no
H311 . C22 . C23 . C24 . 176.7 no
H311 . C22 . C23 . H321 . -2.2 no
C22 . C23 . C24 . C25 . -0.5(11) yes
C22 . C23 . C24 . H351 . -178.7 no
H321 . C23 . C24 . C25 . 178.5 no
H321 . C23 . C24 . H351 . 0.3 no
C23 . C24 . C25 . C20 . 2.1(10) yes
C23 . C24 . C25 . H301 . -177.9 no
H351 . C24 . C25 . C20 . -179.7 no
H351 . C24 . C25 . H301 . 0.3 no
N26 . C27 . C28 . C29 . 176.3(7) yes
N26 . C27 . C28 . H191 . 57.3 no
N26 . C27 . C28 . H192 . -64.5 no
H161 . C27 . C28 . C29 . -61.4 no
H161 . C27 . C28 . H191 . 179.6 no
H161 . C27 . C28 . H192 . 57.8 no
H162 . C27 . C28 . C29 . 55.2 no
H162 . C27 . C28 . H191 . -63.8 no
H162 . C27 . C28 . H192 . 174.4 no
C28 . C27 . N26 . C31 . -67.3(8) yes
C28 . C27 . N26 . C39 . 51.5(8) yes
C28 . C27 . N26 . C35 . 172.0(6) yes
H161 . C27 . N26 . C31 . 169.3 no
H161 . C27 . N26 . C39 . -71.9 no
H161 . C27 . N26 . C35 . 48.6 no
H162 . C27 . N26 . C31 . 55.6 no
H162 . C27 . N26 . C39 . 174.5 no
H162 . C27 . N26 . C35 . -65.0 no
C27 . C28 . C29 . C30 . 177.8(8) yes
C27 . C28 . C29 . H211 . 59.5 no
C27 . C28 . C29 . H212 . -57.4 no
H191 . C28 . C29 . C30 . -62.1 no
H191 . C28 . C29 . H211 . 179.6 no
H191 . C28 . C29 . H212 . 62.7 no
H192 . C28 . C29 . C30 . 55.6 no
H192 . C28 . C29 . H211 . -62.6 no
H192 . C28 . C29 . H212 . -179.6 no
C28 . C29 . C30 . H381 . -61.4 no
C28 . C29 . C30 . H382 . 179.9 no
C28 . C29 . C30 . H383 . 57.5 no
H211 . C29 . C30 . H381 . 57.3 no
H211 . C29 . C30 . H382 . -61.5 no
H211 . C29 . C30 . H383 . 176.1 no
H212 . C29 . C30 . H381 . 173.8 no
H212 . C29 . C30 . H382 . 55.1 no
H212 . C29 . C30 . H383 . -67.3 no
N26 . C31 . C32 . C33 . 172.8(5) yes
N26 . C31 . C32 . H231 . 51.5 no
N26 . C31 . C32 . H232 . -66.5 no
H151 . C31 . C32 . C33 . 53.4 no
H151 . C31 . C32 . H231 . -67.9 no
H151 . C31 . C32 . H232 . 174.1 no
H152 . C31 . C32 . C33 . -65.3 no
H152 . C31 . C32 . H231 . 173.5 no
H152 . C31 . C32 . H232 . 55.5 no
C32 . C31 . N26 . C27 . -66.3(7) yes
C32 . C31 . N26 . C39 . 172.3(5) yes
C32 . C31 . N26 . C35 . 51.2(6) yes
H151 . C31 . N26 . C27 . 53.7 no
H151 . C31 . N26 . C39 . -67.6 no
H151 . C31 . N26 . C35 . 171.2 no
H152 . C31 . N26 . C27 . 170.7 no
H152 . C31 . N26 . C39 . 49.4 no
H152 . C31 . N26 . C35 . -71.8 no
C31 . C32 . C33 . C34 . 177.8(6) yes
C31 . C32 . C33 . H331 . -58.5 no
C31 . C32 . C33 . H332 . 55.4 no
H231 . C32 . C33 . C34 . -60.8 no
H231 . C32 . C33 . H331 . 62.9 no
H231 . C32 . C33 . H332 . 176.9 no
H232 . C32 . C33 . C34 . 55.2 no
H232 . C32 . C33 . H331 . 178.9 no
H232 . C32 . C33 . H332 . -67.1 no
C32 . C33 . C34 . H401 . 63.5 no
C32 . C33 . C34 . H402 . -175.6 no
C32 . C33 . C34 . H403 . -56.2 no
H331 . C33 . C34 . H401 . -58.5 no
H331 . C33 . C34 . H402 . 62.5 no
H331 . C33 . C34 . H403 . -178.1 no
H332 . C33 . C34 . H401 . -174.4 no
H332 . C33 . C34 . H402 . -53.5 no
H332 . C33 . C34 . H403 . 65.9 no
N26 . C35 . C36 . C37 . 177.9(6) yes
N26 . C35 . C36 . H131 . 57.4 no
N26 . C35 . C36 . H132 . -63.3 no
H61 . C35 . C36 . C37 . 58.0 no
H61 . C35 . C36 . H131 . -62.5 no
H61 . C35 . C36 . H132 . 176.8 no
H62 . C35 . C36 . C37 . -60.5 no
H62 . C35 . C36 . H131 . 178.9 no
H62 . C35 . C36 . H132 . 58.3 no
C36 . C35 . N26 . C31 . 60.7(7) yes
C36 . C35 . N26 . C27 . -178.8(6) yes
C36 . C35 . N26 . C39 . -58.1(8) yes
H61 . C35 . N26 . C31 . -177.5 no
H61 . C35 . N26 . C27 . -57.1 no
H61 . C35 . N26 . C39 . 63.6 no
H62 . C35 . N26 . C31 . -62.7 no
H62 . C35 . N26 . C27 . 57.7 no
H62 . C35 . N26 . C39 . 178.4 no
C35 . C36 . C37 . C38 . -179.5(7) yes
C35 . C36 . C37 . H171 . -57.2 no
C35 . C36 . C37 . H172 . 64.2 no
H131 . C36 . C37 . C38 . -59.3 no
H131 . C36 . C37 . H171 . 63.1 no
H131 . C36 . C37 . H172 . -175.5 no
H132 . C36 . C37 . C38 . 58.8 no
H132 . C36 . C37 . H171 . -178.8 no
H132 . C36 . C37 . H172 . -57.5 no
C36 . C37 . C38 . H271 . 174.7 no
C36 . C37 . C38 . H272 . -63.9 no
C36 . C37 . C38 . H273 . 54.9 no
H171 . C37 . C38 . H271 . 51.9 no
H171 . C37 . C38 . H272 . 173.3 no
H171 . C37 . C38 . H273 . -68.0 no
H172 . C37 . C38 . H271 . -67.9 no
H172 . C37 . C38 . H272 . 53.5 no
H172 . C37 . C38 . H273 . 172.3 no
N26 . C39 . C40 . C41 . -178.9(5) yes
N26 . C39 . C40 . H181 . -59.7 no
N26 . C39 . C40 . H182 . 60.4 no
H141 . C39 . C40 . C41 . 63.4 no
H141 . C39 . C40 . H181 . -177.4 no
H141 . C39 . C40 . H182 . -57.3 no
H142 . C39 . C40 . C41 . -55.3 no
H142 . C39 . C40 . H181 . 63.9 no
H142 . C39 . C40 . H182 . -176.0 no
C40 . C39 . N26 . C31 . 179.9(5) yes
C40 . C39 . N26 . C27 . 58.7(7) yes
C40 . C39 . N26 . C35 . -58.8(7) yes
H141 . C39 . N26 . C31 . -60.9 no
H141 . C39 . N26 . C27 . 178.0 no
H141 . C39 . N26 . C35 . 60.5 no
H142 . C39 . N26 . C31 . 54.3 no
H142 . C39 . N26 . C27 . -66.8 no
H142 . C39 . N26 . C35 . 175.7 no
C39 . C40 . C41 . C42 . 178.9(6) yes
C39 . C40 . C41 . H291 . -59.2 no
C39 . C40 . C41 . H292 . 61.1 no
H181 . C40 . C41 . C42 . 57.7 no
H181 . C40 . C41 . H291 . 179.6 no
H181 . C40 . C41 . H292 . -60.1 no
H182 . C40 . C41 . C42 . -60.4 no
H182 . C40 . C41 . H291 . 61.5 no
H182 . C40 . C41 . H292 . -178.2 no
C40 . C41 . C42 . H371 . -55.7 no
C40 . C41 . C42 . H372 . -177.2 no
C40 . C41 . C42 . H373 . 64.8 no
H291 . C41 . C42 . H371 . -176.5 no
H291 . C41 . C42 . H372 . 62.0 no
H291 . C41 . C42 . H373 . -56.0 no
H292 . C41 . C42 . H371 . 62.7 no
H292 . C41 . C42 . H372 . -58.8 no
H292 . C41 . C42 . H373 . -176.8 no
