# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_ljq021
_database_code_depnum_ccdc_archive 'CCDC 1940358'
loop_
_audit_author_name
_audit_author_address
'Bin Li'
;Wuyi University
China
;
_audit_update_record             
;
2019-07-14 deposited with the CCDC.	2020-10-05 downloaded from the CCDC.
;
_audit_creation_date             2018-07-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H25 F3 N O Si'
_chemical_formula_sum            'C17 H25 F3 N O Si'
_chemical_formula_weight         344.47
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.2994(4)
_cell_length_b                   11.9792(9)
_cell_length_c                   18.8409(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1873.17(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4348
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      24.2430
_cell_measurement_theta_min      2.6710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11626
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.015
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  37.00   1.00    3.50    --   11.74 -57.00 150.00   97
  2  ω    -18.00  79.00   1.00    3.50    --   11.74  77.00  60.00   97
  3  ω    -14.00  61.00   1.00    3.50    --   11.74  57.00 -60.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0170158000
_diffrn_orient_matrix_UB_12      -0.0104860000
_diffrn_orient_matrix_UB_13      0.0363069000
_diffrn_orient_matrix_UB_21      -0.0394495000
_diffrn_orient_matrix_UB_22      0.0523473000
_diffrn_orient_matrix_UB_23      0.0025209000
_diffrn_orient_matrix_UB_31      -0.0738890000
_diffrn_orient_matrix_UB_32      -0.0255430000
_diffrn_orient_matrix_UB_33      -0.0096915000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2832
_reflns_number_total             3298
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 992 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0535
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0561P)²+1.2494P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1303
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H11,H11B,H11A} of C11, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  {H14A,H14B,H14C} of C14, {H10A,H10B,H10C} of C10, {H16A,H16B,H16C} of C16,
  {H12A,H12B,H12C} of C12
2. Others
 Sof(H11B)=Sof(H11A)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=1-FVAR(1)
 Sof(H11)=Sof(C0AA)=Sof(H0AA)=Sof(H0AB)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C15(H15A,H15B), C9(H9A,H9B), C13(H13A,H13B), C11(H11B,H11A)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C6(H6), C2(H2), C11(H11)
3.c X=CH2 refined with riding coordinates:
 C0AA(H0AA,H0AB)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C16(H16A,H16B,H16C), C14(H14A,H14B,H14C), C12(H12A,H12B,
 H12C)
;
_atom_sites_solution_hydrogens   geom
_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 0.52400(16) 0.52850(12) 0.64209(6) 0.0402(3) Uani 1 1 d . . . . .
O1 O 0.6560(3) 0.7354(3) 0.56453(15) 0.0365(8) Uani 1 1 d . . . . .
F2 F 0.2832(4) 0.2378(3) 0.44363(18) 0.0625(9) Uani 1 1 d . . . . .
F3 F 0.5300(4) 0.2284(3) 0.4167(2) 0.0810(11) Uani 1 1 d . . . . .
N1 N 0.4608(4) 0.8168(3) 0.49944(18) 0.0323(8) Uani 1 1 d . . . . .
H1 H 0.381067 0.806643 0.471000 0.039 Uiso 1 1 calc R . . . .
F1 F 0.3571(6) 0.2931(3) 0.34200(18) 0.0866(12) Uani 1 1 d . . . . .
C4 C 0.4898(4) 0.6158(4) 0.4961(2) 0.0274(9) Uani 1 1 d . . . . .
C5 C 0.4875(5) 0.5231(4) 0.54247(19) 0.0291(9) Uani 1 1 d . . . . .
C7 C 0.5405(5) 0.7281(4) 0.52347(19) 0.0281(9) Uani 1 1 d . . . . .
C3 C 0.4586(5) 0.6035(4) 0.4239(2) 0.0311(10) Uani 1 1 d . . . . .
H3 H 0.457355 0.666071 0.394682 0.037 Uiso 1 1 calc R . . . .
C6 C 0.4541(5) 0.4198(4) 0.5117(2) 0.0342(10) Uani 1 1 d . . . . .
H6 H 0.448326 0.357039 0.540614 0.041 Uiso 1 1 calc R . . . .
C2 C 0.4293(5) 0.4990(4) 0.3951(2) 0.0343(11) Uani 1 1 d . . . . .
H2 H 0.410041 0.490952 0.346775 0.041 Uiso 1 1 calc R . . . .
C8 C 0.5036(5) 0.9304(4) 0.5196(2) 0.0378(11) Uani 1 1 d . . . . .
H8A H 0.502149 0.977079 0.477504 0.045 Uiso 1 1 calc R . . . .
H8B H 0.612703 0.930545 0.538056 0.045 Uiso 1 1 calc R . . . .
C1 C 0.4291(5) 0.4075(4) 0.4391(2) 0.0367(11) Uani 1 1 d . . . . .
C15 C 0.4196(6) 0.6509(4) 0.6840(2) 0.0438(12) Uani 1 1 d . . . . .
H15A H 0.418134 0.639861 0.735016 0.053 Uiso 1 1 calc R . . . .
H15B H 0.482734 0.717458 0.674626 0.053 Uiso 1 1 calc R . . . .
C10 C 0.4430(6) 1.0957(4) 0.5964(3) 0.0477(12) Uani 1 1 d . . . . .
H10A H 0.453397 1.142950 0.555508 0.072 Uiso 1 1 calc GR . . . .
H10B H 0.543979 1.092668 0.621151 0.072 Uiso 1 1 calc GR . . . .
H10C H 0.361582 1.125258 0.627347 0.072 Uiso 1 1 calc GR . . . .
C17 C 0.4009(7) 0.2931(5) 0.4098(3) 0.0522(13) Uani 1 1 d . . . . .
C9 C 0.3954(6) 0.9790(5) 0.5730(3) 0.0565(15) Uani 1 1 d . . . . .
H9A H 0.393574 0.930586 0.614256 0.068 Uiso 1 1 calc R . . . .
H9B H 0.287107 0.981439 0.553721 0.068 Uiso 1 1 calc R . . . .
C16 C 0.2467(7) 0.6719(5) 0.6590(3) 0.0533(14) Uani 1 1 d . . . . .
H16A H 0.246927 0.688910 0.609244 0.080 Uiso 1 1 calc GR . . . .
H16B H 0.201933 0.733663 0.684880 0.080 Uiso 1 1 calc GR . . . .
H16C H 0.182799 0.606427 0.667339 0.080 Uiso 1 1 calc GR . . . .
C13 C 0.7477(7) 0.5259(5) 0.6594(3) 0.0586(15) Uani 1 1 d . . . . .
H13A H 0.795885 0.473798 0.626230 0.070 Uiso 1 1 calc R . . . .
H13B H 0.790099 0.599294 0.648353 0.070 Uiso 1 1 calc R . . . .
C11 C 0.4304(12) 0.3978(5) 0.6789(3) 0.094(3) Uani 1 1 d . . . . .
H11 H 0.501004 0.338784 0.686669 0.112 Uiso 0.413(15) 1 calc R . P A 1
H11B H 0.350952 0.372039 0.644904 0.112 Uiso 0.587(15) 1 calc R . P A 2
H11A H 0.513929 0.341308 0.681199 0.112 Uiso 0.587(15) 1 calc R . P A 2
C14 C 0.8034(11) 0.4957(10) 0.7314(4) 0.131(4) Uani 1 1 d . . . . .
H14A H 0.919006 0.492316 0.732007 0.196 Uiso 1 1 calc GR . . . .
H14B H 0.760146 0.424233 0.744357 0.196 Uiso 1 1 calc GR . . . .
H14C H 0.767413 0.551014 0.764737 0.196 Uiso 1 1 calc GR . . . .
C0AA C 0.2941(15) 0.3802(11) 0.6936(8) 0.043(5) Uani 0.413(15) 1 d . . P A 1
H0AA H 0.216981 0.435662 0.687235 0.052 Uiso 0.413(15) 1 calc R . P A 1
H0AB H 0.264064 0.310980 0.711626 0.052 Uiso 0.413(15) 1 calc R . P A 1
C12 C 0.3496(16) 0.4022(10) 0.7509(6) 0.071(4) Uani 0.587(15) 1 d . . P A 2
H12A H 0.429019 0.416150 0.786798 0.107 Uiso 0.587(15) 1 calc GR . P A 2
H12B H 0.297356 0.332191 0.760154 0.107 Uiso 0.587(15) 1 calc GR . P A 2
H12C H 0.271004 0.461016 0.751237 0.107 Uiso 0.587(15) 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 C5 1.902(4) . ?
Si1 C15 1.878(5) . ?
Si1 C13 1.885(6) . ?
Si1 C11 1.881(7) . ?
O1 C7 1.235(5) . ?
F2 C17 1.341(6) . ?
F3 C17 1.329(6) . ?
N1 C7 1.331(5) . ?
N1 C8 1.457(6) . ?
F1 C17 1.329(6) . ?
C4 C5 1.413(6) . ?
C4 C7 1.501(6) . ?
C4 C3 1.393(6) . ?
C5 C6 1.394(6) . ?
C3 C2 1.385(6) . ?
C6 C1 1.391(6) . ?
C2 C1 1.374(6) . ?
C8 C9 1.470(6) . ?
C1 C17 1.495(7) . ?
C15 C16 1.531(7) . ?
C10 C9 1.518(7) . ?
C13 C14 1.479(8) . ?
C11 C0AA 1.184(13) . ?
C11 C12 1.513(11) . ?

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
C15 Si1 C5 111.6(2) . . ?
C15 Si1 C13 113.2(3) . . ?
C15 Si1 C11 107.7(3) . . ?
C13 Si1 C5 109.1(2) . . ?
C11 Si1 C5 105.7(3) . . ?
C11 Si1 C13 109.2(4) . . ?
C7 N1 C8 122.4(4) . . ?
C5 C4 C7 119.7(3) . . ?
C3 C4 C5 121.2(4) . . ?
C3 C4 C7 118.9(4) . . ?
C4 C5 Si1 125.5(3) . . ?
C6 C5 Si1 118.2(3) . . ?
C6 C5 C4 116.3(3) . . ?
O1 C7 N1 122.8(4) . . ?
O1 C7 C4 119.8(4) . . ?
N1 C7 C4 117.3(3) . . ?
C2 C3 C4 120.7(4) . . ?
C1 C6 C5 122.2(4) . . ?
C1 C2 C3 119.0(4) . . ?
N1 C8 C9 113.5(4) . . ?
C6 C1 C17 118.9(4) . . ?
C2 C1 C6 120.5(4) . . ?
C2 C1 C17 120.6(4) . . ?
C16 C15 Si1 115.6(3) . . ?
F2 C17 C1 113.1(4) . . ?
F3 C17 F2 104.6(5) . . ?
F3 C17 C1 111.9(4) . . ?
F1 C17 F2 104.9(4) . . ?
F1 C17 F3 108.3(5) . . ?
F1 C17 C1 113.4(5) . . ?
C8 C9 C10 113.9(4) . . ?
C14 C13 Si1 118.1(5) . . ?
C0AA C11 Si1 129.0(9) . . ?
C12 C11 Si1 119.0(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.783
_oxdiff_exptl_absorpt_empirical_full_min 0.571
