# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_8a
_database_code_depnum_ccdc_archive 'CCDC 2171958'
loop_
_audit_author_name
_audit_author_address
'Steven Kelley'
;University of Missouri
United States of America
;
_audit_update_record             
;
2022-05-10 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_8a                  
;
PROBLEM: Hirshfeld Test Diff for    Si1      --C14      .       11.6 s.u.
RESPONSE: This is physically realistic thermal motion for a trimethylsilyl group.
;
_vrf_PLAT029_8a                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.977 Why?
RESPONSE: This is the physical limit for triclinic data collected on a 3-circle goniometer.
;
# Added during the CSD deposition process: Tuesday 10 May 2022 11:56 PM
# end Validation Reply Form

_audit_creation_date             2020-11-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H39 F6 N O4 Si'
_chemical_formula_sum            'C26 H39 F6 N O4 Si'
_chemical_formula_weight         571.67
_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 0.0181 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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
Si Si 0.2541 0.3302 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2552(2)
_cell_length_b                   13.8552(4)
_cell_length_c                   15.7314(5)
_cell_angle_alpha                105.3326(16)
_cell_angle_beta                 99.3403(19)
_cell_angle_gamma                101.6075(17)
_cell_volume                     1454.49(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9791
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      73.55
_cell_measurement_theta_min      2.99
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.598
_exptl_absorpt_coefficient_mu    1.335
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1257 before and 0.0423 after correction.
The Ratio of minimum to maximum transmission is 0.8764.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            51591
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.291
_diffrn_reflns_theta_min         2.992
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker X8 Prospector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multi-layer optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Incoatec IMuS microfocus Cu tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5225
_reflns_number_total             5717
_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       'Bruker Apex3 V.2018.1-0/SAINT V8.38A'
_computing_data_collection       'Bruker Apex3 V.2018.1-0'
_computing_data_reduction        'Bruker Apex3 V.2018.1-0/SAINT V8.38A'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.694
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5717
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+0.6809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0899
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C10(H10), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B),
 C21(H21A,H21B), C22(H22A,H22B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C14(H14A,H14B,H14C), C25(H25A,H25B,H25C), C15(H15A,H15B,
 H15C), C13(H13A,H13B,H13C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.20219(6) 0.99409(3) 0.34658(2) 0.02330(10) Uani 1 1 d . . . . .
O1 O 0.37910(13) 0.71888(7) 0.04418(6) 0.0242(2) Uani 1 1 d . . . . .
F2 F 0.30032(13) 0.93516(7) -0.12688(7) 0.0398(2) Uani 1 1 d . . . . .
O2 O 0.17625(13) 0.85638(6) 0.00894(6) 0.01980(19) Uani 1 1 d . . . . .
F4 F -0.08279(13) 0.88474(7) -0.12308(7) 0.0405(2) Uani 1 1 d . . . . .
F6 F -0.19352(13) 0.73148(7) -0.11868(6) 0.0419(2) Uani 1 1 d . . . . .
F1 F 0.48257(13) 0.85878(9) -0.06392(7) 0.0453(3) Uani 1 1 d . . . . .
F5 F -0.05920(15) 0.75400(9) -0.22627(6) 0.0495(3) Uani 1 1 d . . . . .
O4 O -0.34817(14) 0.51497(7) 0.10658(7) 0.0287(2) Uani 1 1 d . . . . .
O3 O -0.07994(15) 0.45917(7) 0.13460(7) 0.0316(2) Uani 1 1 d . . . . .
N1 N -0.06355(15) 0.77895(8) 0.07267(7) 0.0196(2) Uani 1 1 d . . . . .
F3 F 0.31647(18) 0.78390(9) -0.19869(7) 0.0554(3) Uani 1 1 d . . . . .
C3 C 0.22047(18) 0.87776(10) 0.25471(8) 0.0200(3) Uani 1 1 d . . . . .
C6 C 0.16296(18) 0.64427(9) 0.12238(8) 0.0193(3) Uani 1 1 d . . . . .
H6 H 0.200825 0.578794 0.097361 0.023 Uiso 1 1 calc R . . . .
C7 C -0.05394(18) 0.61955(9) 0.10487(8) 0.0196(3) Uani 1 1 d . . . . .
C9 C 0.23777(18) 0.71976(9) 0.07560(8) 0.0184(2) Uani 1 1 d . . . . .
C26 C -0.1676(2) 0.85989(10) 0.08058(10) 0.0257(3) Uani 1 1 d . . . . .
H26A H -0.306262 0.828015 0.056105 0.039 Uiso 1 1 calc GR . . . .
H26B H -0.121029 0.905850 0.046485 0.039 Uiso 1 1 calc GR . . . .
H26C H -0.145351 0.900018 0.144449 0.039 Uiso 1 1 calc GR . . . .
C4 C 0.22105(18) 0.78996(10) 0.27554(9) 0.0204(3) Uani 1 1 d . . . . .
H4 H 0.192301 0.791591 0.332625 0.024 Uiso 1 1 calc R . . . .
C2 C 0.25207(19) 0.89689(9) 0.16645(8) 0.0204(3) Uani 1 1 d . . . . .
H2A H 0.392058 0.909587 0.168140 0.024 Uiso 1 1 calc R . . . .
H2B H 0.214201 0.961012 0.163878 0.024 Uiso 1 1 calc R . . . .
C11 C 0.3134(2) 0.84376(11) -0.11783(9) 0.0272(3) Uani 1 1 d . . . . .
C8 C -0.14802(19) 0.68883(10) 0.08565(8) 0.0199(3) Uani 1 1 d . . . . .
H8 H -0.283657 0.673243 0.080864 0.024 Uiso 1 1 calc R . . . .
C10 C 0.1469(2) 0.79432(10) -0.08162(9) 0.0222(3) Uani 1 1 d . . . . .
H10 H 0.153024 0.722420 -0.083168 0.027 Uiso 1 1 calc R . . . .
C16 C 0.47745(19) 0.69720(11) 0.24489(9) 0.0233(3) Uani 1 1 d . . . . .
H16A H 0.501511 0.636528 0.202651 0.028 Uiso 1 1 calc R . . . .
H16B H 0.544778 0.760003 0.232701 0.028 Uiso 1 1 calc R . . . .
C24 C -0.1567(2) 0.52392(10) 0.11651(9) 0.0221(3) Uani 1 1 d . . . . .
C1 C 0.14231(18) 0.80961(9) 0.07815(8) 0.0184(2) Uani 1 1 d . . . . .
C5 C 0.25857(19) 0.68871(10) 0.22587(8) 0.0199(3) Uani 1 1 d . . . . .
H5 H 0.200756 0.636440 0.253825 0.024 Uiso 1 1 calc R . . . .
C12 C -0.0482(2) 0.79127(11) -0.13792(10) 0.0295(3) Uani 1 1 d . . . . .
C17 C 0.5632(2) 0.70257(12) 0.34193(9) 0.0273(3) Uani 1 1 d . . . . .
H17A H 0.563157 0.770081 0.383584 0.033 Uiso 1 1 calc R . . . .
H17B H 0.480685 0.647402 0.358380 0.033 Uiso 1 1 calc R . . . .
C18 C 0.7685(2) 0.68997(12) 0.35404(10) 0.0287(3) Uani 1 1 d . . . . .
H18A H 0.851603 0.747835 0.341058 0.034 Uiso 1 1 calc R . . . .
H18B H 0.768899 0.624887 0.308933 0.034 Uiso 1 1 calc R . . . .
C14 C 0.2232(2) 0.96469(12) 0.45664(10) 0.0340(3) Uani 1 1 d . . . . .
H14A H 0.107811 0.911990 0.453761 0.051 Uiso 1 1 calc GR . . . .
H14B H 0.234854 1.027875 0.505662 0.051 Uiso 1 1 calc GR . . . .
H14C H 0.337978 0.938798 0.468141 0.051 Uiso 1 1 calc GR . . . .
C19 C 0.8568(2) 0.68752(12) 0.44840(10) 0.0289(3) Uani 1 1 d . . . . .
H19A H 0.879480 0.756967 0.492474 0.035 Uiso 1 1 calc R . . . .
H19B H 0.763838 0.638040 0.466210 0.035 Uiso 1 1 calc R . . . .
C21 C 1.1398(2) 0.64823(12) 0.54381(10) 0.0297(3) Uani 1 1 d . . . . .
H21A H 1.174464 0.717409 0.589621 0.036 Uiso 1 1 calc R . . . .
H21B H 1.044907 0.601077 0.562871 0.036 Uiso 1 1 calc R . . . .
C22 C 1.3198(2) 0.60843(12) 0.54050(10) 0.0330(3) Uani 1 1 d . . . . .
H22A H 1.413441 0.655285 0.520598 0.040 Uiso 1 1 calc R . . . .
H22B H 1.284271 0.539157 0.494788 0.040 Uiso 1 1 calc R . . . .
C25 C -0.4594(2) 0.43017(11) 0.12820(11) 0.0327(3) Uani 1 1 d . . . . .
H25A H -0.461764 0.364691 0.084194 0.049 Uiso 1 1 calc GR . . . .
H25B H -0.591813 0.437034 0.126014 0.049 Uiso 1 1 calc GR . . . .
H25C H -0.400592 0.430969 0.189111 0.049 Uiso 1 1 calc GR . . . .
C20 C 1.0468(2) 0.65606(12) 0.45248(10) 0.0312(3) Uani 1 1 d . . . . .
H20A H 1.139703 0.707042 0.436127 0.037 Uiso 1 1 calc R . . . .
H20B H 1.023786 0.588083 0.406163 0.037 Uiso 1 1 calc R . . . .
C15 C -0.0329(3) 1.02653(14) 0.32094(11) 0.0418(4) Uani 1 1 d . . . . .
H15A H -0.042765 1.048443 0.266386 0.063 Uiso 1 1 calc GR . . . .
H15B H -0.041111 1.082838 0.372018 0.063 Uiso 1 1 calc GR . . . .
H15C H -0.138835 0.965422 0.310899 0.063 Uiso 1 1 calc GR . . . .
C13 C 0.4035(3) 1.10471(13) 0.35475(12) 0.0472(4) Uani 1 1 d . . . . .
H13A H 0.526610 1.086434 0.367152 0.071 Uiso 1 1 calc GR . . . .
H13B H 0.402754 1.165150 0.403926 0.071 Uiso 1 1 calc GR . . . .
H13C H 0.387640 1.121043 0.297496 0.071 Uiso 1 1 calc GR . . . .
C23 C 1.4172(3) 0.60056(14) 0.63086(11) 0.0420(4) Uani 1 1 d . . . . .
H23A H 1.527007 0.570517 0.623224 0.063 Uiso 1 1 calc GR . . . .
H23B H 1.324195 0.556326 0.652234 0.063 Uiso 1 1 calc GR . . . .
H23C H 1.463117 0.669787 0.675263 0.063 Uiso 1 1 calc GR . . . .


_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 C3 1.9028(13) . ?
Si1 C14 1.8705(15) . ?
Si1 C15 1.8589(17) . ?
Si1 C13 1.8528(18) . ?
O1 C9 1.2092(16) . ?
F2 C11 1.3312(16) . ?
O2 C10 1.4123(15) . ?
O2 C1 1.4359(14) . ?
F4 C12 1.3357(18) . ?
F6 C12 1.3319(17) . ?
F1 C11 1.3173(18) . ?
F5 C12 1.3314(17) . ?
O4 C24 1.3488(17) . ?
O4 C25 1.4375(16) . ?
O3 C24 1.2169(16) . ?
N1 C26 1.4633(16) . ?
N1 C8 1.3579(16) . ?
N1 C1 1.4499(16) . ?
F3 C11 1.3286(17) . ?
C3 C4 1.3415(18) . ?
C3 C2 1.5245(17) . ?
C6 C7 1.5040(18) . ?
C6 C9 1.4961(17) . ?
C6 C5 1.5627(17) . ?
C7 C8 1.3522(18) . ?
C7 C24 1.4561(18) . ?
C9 C1 1.5364(17) . ?
C4 C5 1.5151(17) . ?
C2 C1 1.5463(17) . ?
C11 C10 1.5326(19) . ?
C10 C12 1.530(2) . ?
C16 C5 1.5418(18) . ?
C16 C17 1.5283(18) . ?
C17 C18 1.522(2) . ?
C18 C19 1.5303(19) . ?
C19 C20 1.524(2) . ?
C21 C22 1.520(2) . ?
C21 C20 1.5259(19) . ?
C22 C23 1.523(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
C14 Si1 C3 109.43(6) . . ?
C15 Si1 C3 111.99(7) . . ?
C15 Si1 C14 107.67(8) . . ?
C13 Si1 C3 107.31(7) . . ?
C13 Si1 C14 110.40(8) . . ?
C13 Si1 C15 110.06(9) . . ?
C10 O2 C1 120.45(9) . . ?
C24 O4 C25 117.13(11) . . ?
C8 N1 C26 118.42(11) . . ?
C8 N1 C1 121.75(10) . . ?
C1 N1 C26 117.28(10) . . ?
C4 C3 Si1 117.80(10) . . ?
C4 C3 C2 125.97(11) . . ?
C2 C3 Si1 115.97(9) . . ?
C7 C6 C5 111.70(10) . . ?
C9 C6 C7 110.69(10) . . ?
C9 C6 C5 109.53(10) . . ?
C8 C7 C6 120.12(11) . . ?
C8 C7 C24 121.36(12) . . ?
C24 C7 C6 118.33(11) . . ?
O1 C9 C6 123.30(11) . . ?
O1 C9 C1 119.08(11) . . ?
C6 C9 C1 117.22(10) . . ?
C3 C4 C5 132.60(12) . . ?
C3 C2 C1 116.44(10) . . ?
F2 C11 C10 112.33(11) . . ?
F1 C11 F2 107.15(12) . . ?
F1 C11 F3 107.07(12) . . ?
F1 C11 C10 111.72(11) . . ?
F3 C11 F2 107.00(12) . . ?
F3 C11 C10 111.27(12) . . ?
C7 C8 N1 125.03(12) . . ?
O2 C10 C11 105.87(10) . . ?
O2 C10 C12 111.08(11) . . ?
C12 C10 C11 110.78(11) . . ?
C17 C16 C5 113.45(11) . . ?
O4 C24 C7 112.65(11) . . ?
O3 C24 O4 122.97(12) . . ?
O3 C24 C7 124.37(13) . . ?
O2 C1 N1 109.69(10) . . ?
O2 C1 C9 112.63(10) . . ?
O2 C1 C2 103.04(9) . . ?
N1 C1 C9 112.42(10) . . ?
N1 C1 C2 112.55(10) . . ?
C9 C1 C2 106.12(10) . . ?
C4 C5 C6 115.99(10) . . ?
C4 C5 C16 109.99(10) . . ?
C16 C5 C6 111.82(10) . . ?
F4 C12 C10 112.57(11) . . ?
F6 C12 F4 106.49(13) . . ?
F6 C12 C10 111.36(11) . . ?
F5 C12 F4 107.14(12) . . ?
F5 C12 F6 107.34(12) . . ?
F5 C12 C10 111.62(13) . . ?
C18 C17 C16 112.29(11) . . ?
C17 C18 C19 114.54(12) . . ?
C20 C19 C18 112.48(12) . . ?
C22 C21 C20 112.26(12) . . ?
C21 C22 C23 113.61(13) . . ?
C19 C20 C21 115.40(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol/water'
