#------------------------------------------------------------------------------
#$Date: 2024-07-16 03:10:43 +0200 (Tue 16 de Jul de 2024) $
#$Revision: 293421 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/90/7249049.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_7249049
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         'C35 H53.00 F2 N1 O1 Si1'
_chemical_formula_sum            'C35 H53 F2 N O Si'
_chemical_formula_weight         569.89
_chemical_name_common
'Butan-1-aminium, N,N,N-tributyl, (TB-5-11)-difluoro(4-methoxyphenyl)diphenylsilicate(1-)'
_chemical_name_systematic
'Tetrabutylammonium difluoro(4-methoxyphenyl)diphenylsilicate'
_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                 102.4507(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6320(2)
_cell_length_b                   18.7983(4)
_cell_length_c                   19.1207(4)
_cell_measurement_reflns_used    9121
_cell_measurement_temperature    180
_cell_measurement_theta_max      74.53
_cell_measurement_theta_min      2.37
_cell_volume                     3380.67(12)
_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  0.041
_diffrn_reflns_av_unetI/netI     0.068
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            67833
_diffrn_reflns_theta_full        68.241
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_min         3.336
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.902
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1239.987
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         6188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.0007401
_refine_ls_shift/su_mean         0.0000609
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 1.02P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1119
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1119
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                5558
_reflns_number_total             6188
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   3.28
_oxford_diffrn_Wilson_scale      53.12
_oxford_refine_ls_scale          0.14223(6)
_cod_data_source_file            d4ra04332d2.cif
_cod_data_source_block           I
_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        'C35 H53.00 F2 N1 O1 Si1'
_cod_database_code               7249049
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_r_factor_ref          0.0425
_reflns_number_all               6188
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 0.15575(4) 0.70064(2) 0.624071(18) 0.0368 1.0000 Uani . . . . . .
F2 F 0.24070(8) 0.69014(4) 0.55346(4) 0.0407 1.0000 Uani . . . . . .
F3 F 0.07773(9) 0.71120(5) 0.69666(4) 0.0488 1.0000 Uani . . . . . .
C4 C -0.01096(14) 0.65533(7) 0.57225(6) 0.0347 1.0000 Uani . . . . . .
C5 C -0.14362(14) 0.66570(7) 0.59029(7) 0.0375 1.0000 Uani . . . . . .
C6 C -0.26558(14) 0.63206(7) 0.55466(7) 0.0382 1.0000 Uani . . . . . .
C7 C -0.25957(13) 0.58466(7) 0.49978(7) 0.0358 1.0000 Uani . . . . . .
C8 C -0.13208(14) 0.57303(7) 0.47941(7) 0.0371 1.0000 Uani . . . . . .
C9 C -0.01112(14) 0.60901(7) 0.51526(7) 0.0362 1.0000 Uani . . . . . .
C11 C -0.37995(16) 0.49139(8) 0.42555(9) 0.0499 1.0000 Uani . . . . . .
C12 C 0.16417(15) 0.80140(8) 0.61538(8) 0.0452 1.0000 Uani . . . . . .
C13 C 0.04990(19) 0.84468(10) 0.62218(12) 0.0659 1.0000 Uani . . . . . .
C14 C 0.0494(2) 0.91733(11) 0.61099(13) 0.0792 1.0000 Uani . . . . . .
C15 C 0.1650(3) 0.94999(11) 0.59509(13) 0.0843 1.0000 Uani . . . . . .
C16 C 0.2812(3) 0.90983(12) 0.59076(16) 0.0982 1.0000 Uani . . . . . .
C17 C 0.2789(2) 0.83662(11) 0.59978(13) 0.0723 1.0000 Uani . . . . . .
C18 C 0.30661(14) 0.64750(7) 0.68293(7) 0.0384 1.0000 Uani . . . . . .
C19 C 0.44795(15) 0.65384(8) 0.67646(8) 0.0434 1.0000 Uani . . . . . .
C20 C 0.55818(17) 0.61648(9) 0.72006(9) 0.0531 1.0000 Uani . . . . . .
C21 C 0.52946(19) 0.56957(10) 0.77057(9) 0.0593 1.0000 Uani . . . . . .
C22 C 0.3905(2) 0.56106(9) 0.77789(9) 0.0576 1.0000 Uani . . . . . .
C23 C 0.28163(17) 0.60014(8) 0.73530(8) 0.0456 1.0000 Uani . . . . . .
C25 C 0.22668(14) 0.76421(9) 0.35207(8) 0.0440 1.0000 Uani . . . . . .
C26 C 0.12253(15) 0.76737(10) 0.40097(8) 0.0506 1.0000 Uani . . . . . .
C27 C 0.00208(18) 0.81812(11) 0.36853(10) 0.0627 1.0000 Uani . . . . . .
C28 C -0.1115(2) 0.82087(13) 0.41168(12) 0.0767 1.0000 Uani . . . . . .
C29 C 0.30922(15) 0.64034(8) 0.38800(8) 0.0436 1.0000 Uani . . . . . .
C30 C 0.21761(16) 0.60397(9) 0.32389(9) 0.0511 1.0000 Uani . . . . . .
C31 C 0.17860(18) 0.52951(10) 0.34428(10) 0.0600 1.0000 Uani . . . . . .
C32 C 0.0897(2) 0.48839(11) 0.28300(12) 0.0705 1.0000 Uani . . . . . .
C33 C 0.43689(15) 0.71859(9) 0.31645(8) 0.0440 1.0000 Uani . . . . . .
C34 C 0.56786(16) 0.67181(9) 0.32619(9) 0.0507 1.0000 Uani . . . . . .
C35 C 0.64426(19) 0.68251(11) 0.26567(10) 0.0645 1.0000 Uani . . . . . .
C36 C 0.7770(2) 0.63726(12) 0.27349(12) 0.0739 1.0000 Uani . . . . . .
C37 C 0.44645(15) 0.74064(8) 0.44687(7) 0.0438 1.0000 Uani . . . . . .
C38 C 0.49489(17) 0.81737(9) 0.45044(9) 0.0541 1.0000 Uani . . . . . .
C39 C 0.60592(18) 0.83118(11) 0.51895(10) 0.0619 1.0000 Uani . . . . . .
C40 C 0.6490(2) 0.90891(13) 0.52791(16) 0.0918 1.0000 Uani . . . . . .
O10 O -0.38580(10) 0.55207(5) 0.46963(6) 0.0453 1.0000 Uani . . . . . .
N24 N 0.35478(11) 0.71568(7) 0.37601(6) 0.0405 1.0000 Uani . . . . . .
H51 H -0.1481 0.6966 0.6296 0.0451 1.0000 Uiso R . . . . .
H61 H -0.3589 0.6407 0.5675 0.0431 1.0000 Uiso R . . . . .
H81 H -0.1248 0.5405 0.4417 0.0424 1.0000 Uiso R . . . . .
H91 H 0.0741 0.6010 0.5008 0.0439 1.0000 Uiso R . . . . .
H111 H -0.3503 0.5065 0.3809 0.0703 1.0000 Uiso R . . . . .
H112 H -0.3177 0.4554 0.4508 0.0730 1.0000 Uiso R . . . . .
H113 H -0.4788 0.4734 0.4124 0.0729 1.0000 Uiso R . . . . .
H131 H -0.0327 0.8236 0.6321 0.0765 1.0000 Uiso R . . . . .
H141 H -0.0338 0.9457 0.6120 0.0974 1.0000 Uiso R . . . . .
H151 H 0.1622 1.0002 0.5863 0.0991 1.0000 Uiso R . . . . .
H161 H 0.3617 0.9324 0.5789 0.1141 1.0000 Uiso R . . . . .
H171 H 0.3592 0.8117 0.5927 0.0878 1.0000 Uiso R . . . . .
H191 H 0.4728 0.6836 0.6411 0.0493 1.0000 Uiso R . . . . .
H201 H 0.6552 0.6234 0.7176 0.0642 1.0000 Uiso R . . . . .
H211 H 0.6017 0.5443 0.7993 0.0705 1.0000 Uiso R . . . . .
H221 H 0.3658 0.5308 0.8120 0.0692 1.0000 Uiso R . . . . .
H231 H 0.1861 0.5925 0.7407 0.0547 1.0000 Uiso R . . . . .
H251 H 0.1778 0.7439 0.3042 0.0526 1.0000 Uiso R . . . . .
H252 H 0.2633 0.8105 0.3463 0.0514 1.0000 Uiso R . . . . .
H261 H 0.0823 0.7209 0.4046 0.0604 1.0000 Uiso R . . . . .
H262 H 0.1648 0.7867 0.4468 0.0592 1.0000 Uiso R . . . . .
H271 H -0.0430 0.8031 0.3203 0.0727 1.0000 Uiso R . . . . .
H272 H 0.0447 0.8650 0.3700 0.0764 1.0000 Uiso R . . . . .
H281 H -0.0726 0.8385 0.4604 0.1088 1.0000 Uiso R . . . . .
H282 H -0.1916 0.8523 0.3873 0.1106 1.0000 Uiso R . . . . .
H283 H -0.1490 0.7716 0.4129 0.1088 1.0000 Uiso R . . . . .
H291 H 0.2550 0.6428 0.4248 0.0501 1.0000 Uiso R . . . . .
H292 H 0.3987 0.6137 0.4038 0.0496 1.0000 Uiso R . . . . .
H301 H 0.1283 0.6294 0.3051 0.0618 1.0000 Uiso R . . . . .
H302 H 0.2688 0.6002 0.2833 0.0591 1.0000 Uiso R . . . . .
H311 H 0.2643 0.5027 0.3612 0.0704 1.0000 Uiso R . . . . .
H312 H 0.1221 0.5331 0.3813 0.0722 1.0000 Uiso R . . . . .
H321 H 0.0042 0.5109 0.2662 0.1019 1.0000 Uiso R . . . . .
H322 H 0.1349 0.4858 0.2442 0.1025 1.0000 Uiso R . . . . .
H323 H 0.0736 0.4414 0.2979 0.1033 1.0000 Uiso R . . . . .
H331 H 0.4583 0.7665 0.3119 0.0530 1.0000 Uiso R . . . . .
H332 H 0.3733 0.7039 0.2719 0.0546 1.0000 Uiso R . . . . .
H341 H 0.6361 0.6831 0.3708 0.0600 1.0000 Uiso R . . . . .
H342 H 0.5426 0.6235 0.3276 0.0614 1.0000 Uiso R . . . . .
H351 H 0.6666 0.7336 0.2645 0.0768 1.0000 Uiso R . . . . .
H352 H 0.5835 0.6738 0.2213 0.0754 1.0000 Uiso R . . . . .
H361 H 0.8174 0.6445 0.2324 0.1103 1.0000 Uiso R . . . . .
H362 H 0.8464 0.6507 0.3181 0.1124 1.0000 Uiso R . . . . .
H363 H 0.7561 0.5882 0.2772 0.1116 1.0000 Uiso R . . . . .
H371 H 0.3940 0.7318 0.4835 0.0509 1.0000 Uiso R . . . . .
H372 H 0.5284 0.7108 0.4556 0.0487 1.0000 Uiso R . . . . .
H381 H 0.4150 0.8487 0.4491 0.0649 1.0000 Uiso R . . . . .
H382 H 0.5356 0.8274 0.4095 0.0635 1.0000 Uiso R . . . . .
H391 H 0.6886 0.8028 0.5171 0.0727 1.0000 Uiso R . . . . .
H392 H 0.5686 0.8143 0.5606 0.0727 1.0000 Uiso R . . . . .
H401 H 0.6857 0.9254 0.4864 0.1280 1.0000 Uiso R . . . . .
H402 H 0.5717 0.9384 0.5316 0.1292 1.0000 Uiso R . . . . .
H403 H 0.7282 0.9148 0.5725 0.1304 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 . 177.72(4) yes
F2 . Si1 . C4 . 91.75(5) yes
F3 . Si1 . C4 . 90.31(5) yes
F2 . Si1 . C12 . 90.53(5) yes
F3 . Si1 . C12 . 89.42(6) yes
C4 . Si1 . C12 . 116.62(6) yes
F2 . Si1 . C18 . 88.43(5) yes
F3 . Si1 . C18 . 89.67(5) yes
C4 . Si1 . C18 . 121.47(6) yes
C12 . Si1 . C18 . 121.91(6) yes
Si1 . C4 . C5 . 121.39(10) yes
Si1 . C4 . C9 . 123.13(10) yes
C5 . C4 . C9 . 115.47(12) yes
C4 . C5 . C6 . 122.52(12) yes
C4 . C5 . H51 . 118.2 no
C6 . C5 . H51 . 119.3 no
C5 . C6 . C7 . 119.91(12) yes
C5 . C6 . H61 . 121.5 no
C7 . C6 . H61 . 118.6 no
C6 . C7 . C8 . 119.92(12) yes
C6 . C7 . O10 . 115.26(12) yes
C8 . C7 . O10 . 124.82(12) yes
C7 . C8 . C9 . 118.93(12) yes
C7 . C8 . H81 . 121.7 no
C9 . C8 . H81 . 119.4 no
C4 . C9 . C8 . 123.20(12) yes
C4 . C9 . H91 . 118.6 no
C8 . C9 . H91 . 118.2 no
O10 . C11 . H111 . 109.5 no
O10 . C11 . H112 . 111.4 no
H111 . C11 . H112 . 111.5 no
O10 . C11 . H113 . 105.3 no
H111 . C11 . H113 . 108.5 no
H112 . C11 . H113 . 110.4 no
Si1 . C12 . C13 . 121.45(13) yes
Si1 . C12 . C17 . 123.32(13) yes
C13 . C12 . C17 . 115.19(17) yes
C12 . C13 . C14 . 122.50(19) yes
C12 . C13 . H131 . 119.3 no
C14 . C13 . H131 . 118.1 no
C13 . C14 . C15 . 120.3(2) yes
C13 . C14 . H141 . 121.1 no
C15 . C14 . H141 . 118.5 no
C14 . C15 . C16 . 118.9(2) yes
C14 . C15 . H151 . 119.3 no
C16 . C15 . H151 . 121.7 no
C15 . C16 . C17 . 120.3(2) yes
C15 . C16 . H161 . 119.1 no
C17 . C16 . H161 . 120.5 no
C16 . C17 . C12 . 122.67(19) yes
C16 . C17 . H171 . 116.2 no
C12 . C17 . H171 . 121.1 no
Si1 . C18 . C19 . 122.21(11) yes
Si1 . C18 . C23 . 121.77(11) yes
C19 . C18 . C23 . 116.01(13) yes
C18 . C19 . C20 . 122.40(15) yes
C18 . C19 . H191 . 120.9 no
C20 . C19 . H191 . 116.7 no
C19 . C20 . C21 . 120.02(16) yes
C19 . C20 . H201 . 122.1 no
C21 . C20 . H201 . 117.9 no
C20 . C21 . C22 . 119.26(15) yes
C20 . C21 . H211 . 120.6 no
C22 . C21 . H211 . 120.1 no
C21 . C22 . C23 . 120.20(16) yes
C21 . C22 . H221 . 122.5 no
C23 . C22 . H221 . 117.2 no
C18 . C23 . C22 . 122.07(15) yes
C18 . C23 . H231 . 119.3 no
C22 . C23 . H231 . 118.5 no
C26 . C25 . N24 . 116.09(11) yes
C26 . C25 . H251 . 109.5 no
N24 . C25 . H251 . 103.6 no
C26 . C25 . H252 . 110.3 no
N24 . C25 . H252 . 106.5 no
H251 . C25 . H252 . 110.6 no
C25 . C26 . C27 . 108.70(12) yes
C25 . C26 . H261 . 109.8 no
C27 . C26 . H261 . 108.3 no
C25 . C26 . H262 . 111.9 no
C27 . C26 . H262 . 105.7 no
H261 . C26 . H262 . 112.2 no
C26 . C27 . C28 . 112.15(15) yes
C26 . C27 . H271 . 110.4 no
C28 . C27 . H271 . 107.5 no
C26 . C27 . H272 . 106.0 no
C28 . C27 . H272 . 107.8 no
H271 . C27 . H272 . 113.1 no
C27 . C28 . H281 . 110.9 no
C27 . C28 . H282 . 110.1 no
H281 . C28 . H282 . 109.9 no
C27 . C28 . H283 . 106.9 no
H281 . C28 . H283 . 110.9 no
H282 . C28 . H283 . 108.2 no
C30 . C29 . N24 . 115.97(11) yes
C30 . C29 . H291 . 107.4 no
N24 . C29 . H291 . 106.7 no
C30 . C29 . H292 . 109.8 no
N24 . C29 . H292 . 105.0 no
H291 . C29 . H292 . 112.0 no
C29 . C30 . C31 . 109.98(13) yes
C29 . C30 . H301 . 112.9 no
C31 . C30 . H301 . 107.2 no
C29 . C30 . H302 . 111.0 no
C31 . C30 . H302 . 108.8 no
H301 . C30 . H302 . 106.7 no
C30 . C31 . C32 . 113.76(15) yes
C30 . C31 . H311 . 109.1 no
C32 . C31 . H311 . 107.1 no
C30 . C31 . H312 . 109.0 no
C32 . C31 . H312 . 106.6 no
H311 . C31 . H312 . 111.2 no
C31 . C32 . H321 . 110.6 no
C31 . C32 . H322 . 111.0 no
H321 . C32 . H322 . 106.3 no
C31 . C32 . H323 . 110.2 no
H321 . C32 . H323 . 110.0 no
H322 . C32 . H323 . 108.8 no
C34 . C33 . N24 . 116.13(11) yes
C34 . C33 . H331 . 112.1 no
N24 . C33 . H331 . 105.4 no
C34 . C33 . H332 . 107.0 no
N24 . C33 . H332 . 108.3 no
H331 . C33 . H332 . 107.7 no
C33 . C34 . C35 . 110.98(13) yes
C33 . C34 . H341 . 111.4 no
C35 . C34 . H341 . 106.9 no
C33 . C34 . H342 . 110.5 no
C35 . C34 . H342 . 108.7 no
H341 . C34 . H342 . 108.2 no
C34 . C35 . C36 . 112.89(15) yes
C34 . C35 . H351 . 107.0 no
C36 . C35 . H351 . 111.4 no
C34 . C35 . H352 . 111.0 no
C36 . C35 . H352 . 109.9 no
H351 . C35 . H352 . 104.3 no
C35 . C36 . H361 . 108.8 no
C35 . C36 . H362 . 109.7 no
H361 . C36 . H362 . 110.6 no
C35 . C36 . H363 . 111.4 no
H361 . C36 . H363 . 109.2 no
H362 . C36 . H363 . 107.2 no
C38 . C37 . N24 . 116.60(12) yes
C38 . C37 . H371 . 109.6 no
N24 . C37 . H371 . 107.5 no
C38 . C37 . H372 . 108.5 no
N24 . C37 . H372 . 105.9 no
H371 . C37 . H372 . 108.4 no
C37 . C38 . C39 . 110.71(14) yes
C37 . C38 . H381 . 110.1 no
C39 . C38 . H381 . 109.1 no
C37 . C38 . H382 . 108.9 no
C39 . C38 . H382 . 109.3 no
H381 . C38 . H382 . 108.6 no
C38 . C39 . C40 . 112.63(18) yes
C38 . C39 . H391 . 107.8 no
C40 . C39 . H391 . 109.2 no
C38 . C39 . H392 . 109.0 no
C40 . C39 . H392 . 110.7 no
H391 . C39 . H392 . 107.3 no
C39 . C40 . H401 . 110.4 no
C39 . C40 . H402 . 111.9 no
H401 . C40 . H402 . 107.5 no
C39 . C40 . H403 . 109.6 no
H401 . C40 . H403 . 107.7 no
H402 . C40 . H403 . 109.6 no
C11 . O10 . C7 . 117.44(11) yes
C25 . N24 . C37 . 111.06(12) yes
C25 . N24 . C33 . 105.76(10) yes
C37 . N24 . C33 . 111.08(10) yes
C25 . N24 . C29 . 111.29(10) yes
C37 . N24 . C29 . 106.54(10) yes
C33 . N24 . C29 . 111.19(12) 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 . 1.7343(8) yes
Si1 . F3 . 1.7264(8) yes
Si1 . C4 . 1.8972(14) yes
Si1 . C12 . 1.9045(17) yes
Si1 . C18 . 1.9160(14) yes
C4 . C5 . 1.4071(18) yes
C4 . C9 . 1.3947(18) yes
C5 . C6 . 1.3780(19) yes
C5 . H51 . 0.958 no
C6 . C7 . 1.3873(19) yes
C6 . H61 . 0.994 no
C7 . C8 . 1.3833(19) yes
C7 . O10 . 1.3725(16) yes
C8 . C9 . 1.3929(19) yes
C8 . H81 . 0.960 no
C9 . H91 . 0.934 no
C11 . O10 . 1.4267(18) yes
C11 . H111 . 0.998 no
C11 . H112 . 0.961 no
C11 . H113 . 0.991 no
C12 . C13 . 1.397(2) yes
C12 . C17 . 1.375(2) yes
C13 . C14 . 1.382(3) yes
C13 . H131 . 0.944 no
C14 . C15 . 1.362(3) yes
C14 . H141 . 0.966 no
C15 . C16 . 1.367(3) yes
C15 . H151 . 0.957 no
C16 . C17 . 1.388(3) yes
C16 . H161 . 0.953 no
C17 . H171 . 0.939 no
C18 . C19 . 1.398(2) yes
C18 . C23 . 1.399(2) yes
C19 . C20 . 1.391(2) yes
C19 . H191 . 0.947 no
C20 . C21 . 1.379(3) yes
C20 . H201 . 0.955 no
C21 . C22 . 1.385(3) yes
C21 . H211 . 0.921 no
C22 . C23 . 1.391(2) yes
C22 . H221 . 0.934 no
C23 . H231 . 0.959 no
C25 . C26 . 1.513(2) yes
C25 . N24 . 1.5235(16) yes
C25 . H251 . 1.010 no
C25 . H252 . 0.954 no
C26 . C27 . 1.527(2) yes
C26 . H261 . 0.965 no
C26 . H262 . 0.954 no
C27 . C28 . 1.507(2) yes
C27 . H271 . 0.973 no
C27 . H272 . 0.971 no
C28 . H281 . 0.984 no
C28 . H282 . 1.002 no
C28 . H283 . 0.996 no
C29 . C30 . 1.511(2) yes
C29 . N24 . 1.5146(19) yes
C29 . H291 . 0.964 no
C29 . H292 . 0.986 no
C30 . C31 . 1.522(2) yes
C30 . H301 . 0.981 no
C30 . H302 . 1.007 no
C31 . C32 . 1.507(3) yes
C31 . H311 . 0.962 no
C31 . H312 . 0.984 no
C32 . H321 . 0.920 no
C32 . H322 . 0.938 no
C32 . H323 . 0.950 no
C33 . C34 . 1.516(2) yes
C33 . N24 . 1.5211(17) yes
C33 . H331 . 0.932 no
C33 . H332 . 0.976 no
C34 . C35 . 1.513(2) yes
C34 . H341 . 0.981 no
C34 . H342 . 0.942 no
C35 . C36 . 1.516(2) yes
C35 . H351 . 0.985 no
C35 . H352 . 0.936 no
C36 . H361 . 0.959 no
C36 . H362 . 0.996 no
C36 . H363 . 0.950 no
C37 . C38 . 1.513(2) yes
C37 . N24 . 1.5231(19) yes
C37 . H371 . 0.962 no
C37 . H372 . 0.953 no
C38 . C39 . 1.524(2) yes
C38 . H381 . 0.965 no
C38 . H382 . 0.966 no
C39 . C40 . 1.519(3) yes
C39 . H391 . 0.966 no
C39 . H392 . 0.993 no
C40 . H401 . 0.986 no
C40 . H402 . 0.942 no
C40 . H403 . 1.020 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
C29 . H292 . O10 1_655 168 0.99 2.47 3.441(2) 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 . -159.0(3) yes
F2 . Si1 . C4 . C9 . 22.2(3) yes
F3 . Si1 . C4 . C5 . 22.0(3) yes
F3 . Si1 . C4 . C9 . -156.8(3) yes
C12 . Si1 . C4 . C5 . -67.5(3) yes
C12 . Si1 . C4 . C9 . 113.7(3) yes
C18 . Si1 . C4 . C5 . 111.8(3) yes
C18 . Si1 . C4 . C9 . -67.0(3) yes
F2 . Si1 . C12 . C13 . 139.4(3) yes
F2 . Si1 . C12 . C17 . -38.4(4) yes
F3 . Si1 . C12 . C13 . -42.9(3) yes
F3 . Si1 . C12 . C17 . 139.4(4) yes
C4 . Si1 . C12 . C13 . 47.1(4) yes
C4 . Si1 . C12 . C17 . -130.6(4) yes
C18 . Si1 . C12 . C13 . -132.2(3) yes
C18 . Si1 . C12 . C17 . 50.1(4) yes
F2 . Si1 . C18 . C19 . 36.9(3) yes
F2 . Si1 . C18 . C23 . -143.4(3) yes
F3 . Si1 . C18 . C19 . -141.8(3) yes
F3 . Si1 . C18 . C23 . 37.9(3) yes
C4 . Si1 . C18 . C19 . 128.0(3) yes
C4 . Si1 . C18 . C23 . -52.3(3) yes
C12 . Si1 . C18 . C19 . -52.7(3) yes
C12 . Si1 . C18 . C23 . 127.0(3) yes
Si1 . C4 . C5 . C6 . -178.35(19) yes
Si1 . C4 . C5 . H51 . 0.2 no
C9 . C4 . C5 . C6 . 0.5(3) yes
C9 . C4 . C5 . H51 . 179.1 no
Si1 . C4 . C9 . C8 . 176.78(19) yes
Si1 . C4 . C9 . H91 . -2.2 no
C5 . C4 . C9 . C8 . -2.1(3) yes
C5 . C4 . C9 . H91 . 178.9 no
C4 . C5 . C6 . C7 . 1.5(3) yes
C4 . C5 . C6 . H61 . -178.8 no
H51 . C5 . C6 . C7 . -177.1 no
H51 . C5 . C6 . H61 . 2.6 no
C5 . C6 . C7 . C8 . -2.1(3) yes
C5 . C6 . C7 . O10 . 177.7(2) yes
H61 . C6 . C7 . C8 . 178.2 no
H61 . C6 . C7 . O10 . -2.1 no
C6 . C7 . C8 . C9 . 0.6(3) yes
C6 . C7 . C8 . H81 . 179.9 no
O10 . C7 . C8 . C9 . -179.1(2) yes
O10 . C7 . C8 . H81 . 0.1 no
C6 . C7 . O10 . C11 . -165.5(2) yes
C8 . C7 . O10 . C11 . 14.2(3) yes
C7 . C8 . C9 . C4 . 1.6(3) yes
C7 . C8 . C9 . H91 . -179.5 no
H81 . C8 . C9 . C4 . -177.7 no
H81 . C8 . C9 . H91 . 1.3 no
H111 . C11 . O10 . C7 . -68.1 no
H112 . C11 . O10 . C7 . 55.7 no
H113 . C11 . O10 . C7 . 175.4 no
Si1 . C12 . C13 . C14 . -175.2(3) yes
Si1 . C12 . C13 . H131 . 1.1 no
C17 . C12 . C13 . C14 . 2.7(5) yes
C17 . C12 . C13 . H131 . 179.0 no
Si1 . C12 . C17 . C16 . 177.3(4) yes
Si1 . C12 . C17 . H171 . -0.1 no
C13 . C12 . C17 . C16 . -0.5(6) yes
C13 . C12 . C17 . H171 . -177.9 no
C12 . C13 . C14 . C15 . -2.4(6) yes
C12 . C13 . C14 . H141 . 174.7 no
H131 . C13 . C14 . C15 . -178.7 no
H131 . C13 . C14 . H141 . -1.6 no
C13 . C14 . C15 . C16 . -0.3(7) yes
C13 . C14 . C15 . H151 . 178.5 no
H141 . C14 . C15 . C16 . -177.4 no
H141 . C14 . C15 . H151 . 1.3 no
C14 . C15 . C16 . C17 . 2.4(8) yes
C14 . C15 . C16 . H161 . 179.1 no
H151 . C15 . C16 . C17 . -176.3 no
H151 . C15 . C16 . H161 . 0.3 no
C15 . C16 . C17 . C12 . -2.0(8) yes
C15 . C16 . C17 . H171 . 175.5 no
H161 . C16 . C17 . C12 . -178.6 no
H161 . C16 . C17 . H171 . -1.1 no
Si1 . C18 . C19 . C20 . 178.6(2) yes
Si1 . C18 . C19 . H191 . -2.4 no
C23 . C18 . C19 . C20 . -1.1(4) yes
C23 . C18 . C19 . H191 . 177.8 no
Si1 . C18 . C23 . C22 . 179.6(2) yes
Si1 . C18 . C23 . H231 . 2.5 no
C19 . C18 . C23 . C22 . -0.7(4) yes
C19 . C18 . C23 . H231 . -177.7 no
C18 . C19 . C20 . C21 . 1.9(4) yes
C18 . C19 . C20 . H201 . -175.7 no
H191 . C19 . C20 . C21 . -177.0 no
H191 . C19 . C20 . H201 . 5.4 no
C19 . C20 . C21 . C22 . -0.9(4) yes
C19 . C20 . C21 . H211 . 179.4 no
H201 . C20 . C21 . C22 . 176.8 no
H201 . C20 . C21 . H211 . -2.9 no
C20 . C21 . C22 . C23 . -0.8(4) yes
C20 . C21 . C22 . H221 . -178.5 no
H211 . C21 . C22 . C23 . 178.9 no
H211 . C21 . C22 . H221 . 1.2 no
C21 . C22 . C23 . C18 . 1.6(4) yes
C21 . C22 . C23 . H231 . 178.7 no
H221 . C22 . C23 . C18 . 179.5 no
H221 . C22 . C23 . H231 . -3.5 no
N24 . C25 . C26 . C27 . -179.9(3) yes
N24 . C25 . C26 . H261 . -61.6 no
N24 . C25 . C26 . H262 . 63.7 no
H251 . C25 . C26 . C27 . -63.1 no
H251 . C25 . C26 . H261 . 55.2 no
H251 . C25 . C26 . H262 . -179.6 no
H252 . C25 . C26 . C27 . 58.8 no
H252 . C25 . C26 . H261 . 177.1 no
H252 . C25 . C26 . H262 . -57.6 no
C26 . C25 . N24 . C37 . -62.6(4) yes
C26 . C25 . N24 . C33 . 176.8(3) yes
C26 . C25 . N24 . C29 . 55.9(4) yes
H251 . C25 . N24 . C37 . 177.4 no
H251 . C25 . N24 . C33 . 56.8 no
H251 . C25 . N24 . C29 . -64.1 no
H252 . C25 . N24 . C37 . 60.7 no
H252 . C25 . N24 . C33 . -59.9 no
H252 . C25 . N24 . C29 . 179.2 no
C25 . C26 . C27 . C28 . 176.4(4) yes
C25 . C26 . C27 . H271 . 56.6 no
C25 . C26 . C27 . H272 . -66.2 no
H261 . C26 . C27 . C28 . 57.2 no
H261 . C26 . C27 . H271 . -62.7 no
H261 . C26 . C27 . H272 . 174.6 no
H262 . C26 . C27 . C28 . -63.2 no
H262 . C26 . C27 . H271 . 176.9 no
H262 . C26 . C27 . H272 . 54.2 no
C26 . C27 . C28 . H281 . 61.7 no
C26 . C27 . C28 . H282 . -176.5 no
C26 . C27 . C28 . H283 . -59.3 no
H271 . C27 . C28 . H281 . -176.8 no
H271 . C27 . C28 . H282 . -55.0 no
H271 . C27 . C28 . H283 . 62.2 no
H272 . C27 . C28 . H281 . -54.6 no
H272 . C27 . C28 . H282 . 67.1 no
H272 . C27 . C28 . H283 . -175.6 no
N24 . C29 . C30 . C31 . -179.1(3) yes
N24 . C29 . C30 . H301 . -59.4 no
N24 . C29 . C30 . H302 . 60.4 no
H291 . C29 . C30 . C31 . -60.0 no
H291 . C29 . C30 . H301 . 59.8 no
H291 . C29 . C30 . H302 . 179.6 no
H292 . C29 . C30 . C31 . 62.1 no
H292 . C29 . C30 . H301 . -178.2 no
H292 . C29 . C30 . H302 . -58.4 no
C30 . C29 . N24 . C25 . 59.5(3) yes
C30 . C29 . N24 . C37 . -179.3(2) yes
C30 . C29 . N24 . C33 . -58.1(3) yes
H291 . C29 . N24 . C25 . -60.1 no
H291 . C29 . N24 . C37 . 61.1 no
H291 . C29 . N24 . C33 . -177.7 no
H292 . C29 . N24 . C25 . -179.2 no
H292 . C29 . N24 . C37 . -58.0 no
H292 . C29 . N24 . C33 . 63.2 no
C29 . C30 . C31 . C32 . -178.7(3) yes
C29 . C30 . C31 . H311 . -59.1 no
C29 . C30 . C31 . H312 . 62.5 no
H301 . C30 . C31 . C32 . 58.2 no
H301 . C30 . C31 . H311 . 177.8 no
H301 . C30 . C31 . H312 . -60.6 no
H302 . C30 . C31 . C32 . -56.9 no
H302 . C30 . C31 . H311 . 62.7 no
H302 . C30 . C31 . H312 . -175.6 no
C30 . C31 . C32 . H321 . -61.9 no
C30 . C31 . C32 . H322 . 55.8 no
C30 . C31 . C32 . H323 . 176.3 no
H311 . C31 . C32 . H321 . 177.4 no
H311 . C31 . C32 . H322 . -64.9 no
H311 . C31 . C32 . H323 . 55.6 no
H312 . C31 . C32 . H321 . 58.2 no
H312 . C31 . C32 . H322 . 175.9 no
H312 . C31 . C32 . H323 . -63.6 no
N24 . C33 . C34 . C35 . -176.9(3) yes
N24 . C33 . C34 . H341 . -57.9 no
N24 . C33 . C34 . H342 . 62.5 no
H331 . C33 . C34 . C35 . -55.6 no
H331 . C33 . C34 . H341 . 63.4 no
H331 . C33 . C34 . H342 . -176.3 no
H332 . C33 . C34 . C35 . 62.1 no
H332 . C33 . C34 . H341 . -178.9 no
H332 . C33 . C34 . H342 . -58.5 no
C34 . C33 . N24 . C25 . -177.6(3) yes
C34 . C33 . N24 . C37 . 61.8(4) yes
C34 . C33 . N24 . C29 . -56.7(4) yes
H331 . C33 . N24 . C25 . 57.6 no
H331 . C33 . N24 . C37 . -63.0 no
H331 . C33 . N24 . C29 . 178.5 no
H332 . C33 . N24 . C25 . -57.4 no
H332 . C33 . N24 . C37 . -178.0 no
H332 . C33 . N24 . C29 . 63.6 no
C33 . C34 . C35 . C36 . 179.4(4) yes
C33 . C34 . C35 . H351 . 56.6 no
C33 . C34 . C35 . H352 . -56.6 no
H341 . C34 . C35 . C36 . 57.8 no
H341 . C34 . C35 . H351 . -65.1 no
H341 . C34 . C35 . H352 . -178.3 no
H342 . C34 . C35 . C36 . -58.9 no
H342 . C34 . C35 . H351 . 178.3 no
H342 . C34 . C35 . H352 . 65.1 no
C34 . C35 . C36 . H361 . 176.9 no
C34 . C35 . C36 . H362 . -62.1 no
C34 . C35 . C36 . H363 . 56.5 no
H351 . C35 . C36 . H361 . -62.8 no
H351 . C35 . C36 . H362 . 58.3 no
H351 . C35 . C36 . H363 . 176.9 no
H352 . C35 . C36 . H361 . 52.3 no
H352 . C35 . C36 . H362 . 173.4 no
H352 . C35 . C36 . H363 . -68.1 no
N24 . C37 . C38 . C39 . -169.9(2) yes
N24 . C37 . C38 . H381 . 69.3 no
N24 . C37 . C38 . H382 . -49.7 no
H371 . C37 . C38 . C39 . 67.7 no
H371 . C37 . C38 . H381 . -53.0 no
H371 . C37 . C38 . H382 . -172.1 no
H372 . C37 . C38 . C39 . -50.5 no
H372 . C37 . C38 . H381 . -171.3 no
H372 . C37 . C38 . H382 . 69.7 no
C38 . C37 . N24 . C25 . -53.5(3) yes
C38 . C37 . N24 . C33 . 63.9(3) yes
C38 . C37 . N24 . C29 . -174.8(2) yes
H371 . C37 . N24 . C25 . 70.0 no
H371 . C37 . N24 . C33 . -172.6 no
H371 . C37 . N24 . C29 . -51.4 no
H372 . C37 . N24 . C25 . -174.3 no
H372 . C37 . N24 . C33 . -56.9 no
H372 . C37 . N24 . C29 . 64.4 no
C37 . C38 . C39 . C40 . -175.3(3) yes
C37 . C38 . C39 . H391 . 64.2 no
C37 . C38 . C39 . H392 . -51.9 no
H381 . C38 . C39 . C40 . -53.9 no
H381 . C38 . C39 . H391 . -174.5 no
H381 . C38 . C39 . H392 . 69.4 no
H382 . C38 . C39 . C40 . 64.7 no
H382 . C38 . C39 . H391 . -55.8 no
H382 . C38 . C39 . H392 . -172.0 no
C38 . C39 . C40 . H401 . -57.5 no
C38 . C39 . C40 . H402 . 62.2 no
C38 . C39 . C40 . H403 . -176.0 no
H391 . C39 . C40 . H401 . 62.2 no
H391 . C39 . C40 . H402 . -178.1 no
H391 . C39 . C40 . H403 . -56.3 no
H392 . C39 . C40 . H401 . -179.9 no
H392 . C39 . C40 . H402 . -60.2 no
H392 . C39 . C40 . H403 . 61.6 no
