# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1987499'
loop_
_audit_author_name
_audit_author_address
'Kohei Sekine'
;Kyushu University
Japan
;
_audit_update_record             
;
2020-03-02 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;
_audit_creation_date             2020-02-03
_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         'C H2 Cl2, C22 H16 F2 N2 Si'
_chemical_formula_sum            'C23 H18 Cl2 F2 N2 Si'
_chemical_formula_weight         459.38
_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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.0006(3)
_cell_length_b                   16.2355(4)
_cell_length_c                   14.0783(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.804(3)
_cell_angle_gamma                90
_cell_volume                     2042.76(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7661
_cell_measurement_temperature    123
_cell_measurement_theta_max      29.2720
_cell_measurement_theta_min      2.4720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.408
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.494
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12122
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.391
_diffrn_reflns_theta_min         2.509
_diffrn_ambient_temperature      123
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00 -31.00   0.50    0.54    --  -17.60  45.00 120.00  148
  2  ω      4.00  68.00   0.50    0.54    --  -17.60  45.00 120.00  128
  3  ω    -79.00  65.00   0.50    0.54    --  -17.60  45.00   0.00  288
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC HyPix-6000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              FR-E+
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4291
_reflns_number_total             4808
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4808
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²+0.8272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0843
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C11(H11), C22(H22), C16(H16), C2(H2), C14(H14), C5(H5), C4(H4),
 C21(H21), C19(H19), C20(H20), C10(H10), C8(H8), C15(H15), C3(H3), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cl2 Cl 0.20843(4) 0.34791(2) 0.81148(3) 0.02642(9) Uani 1 1 d . . . . .
Si1 Si 0.38029(4) 0.62729(2) 0.65869(2) 0.01452(9) Uani 1 1 d . . . . .
Cl1 Cl 0.06275(4) 0.49727(2) 0.86633(3) 0.03464(11) Uani 1 1 d . . . . .
F1 F 0.39114(8) 0.52573(4) 0.64709(5) 0.01987(17) Uani 1 1 d . . . . .
F2 F 0.23098(8) 0.62712(5) 0.71735(6) 0.01966(17) Uani 1 1 d . . . . .
N2 N 0.57974(12) 0.63979(6) 0.59395(8) 0.0158(2) Uani 1 1 d . . . . .
N1 N 0.37388(11) 0.75628(6) 0.65777(8) 0.0157(2) Uani 1 1 d . . . . .
C12 C 0.52275(14) 0.63197(7) 0.77058(9) 0.0159(2) Uani 1 1 d . . . . .
C7 C 0.29264(14) 0.78767(8) 0.57890(9) 0.0169(2) Uani 1 1 d . . . . .
C18 C 0.70460(14) 0.64212(7) 0.65781(10) 0.0164(2) Uani 1 1 d . . . . .
C13 C 0.48844(15) 0.62969(8) 0.86464(10) 0.0195(3) Uani 1 1 d . . . . .
H13 H 0.389240 0.623551 0.875774 0.023 Uiso 1 1 calc R . . . .
C1 C 0.27143(13) 0.64408(8) 0.53562(9) 0.0160(2) Uani 1 1 d . . . . .
C17 C 0.67323(14) 0.64025(7) 0.75753(9) 0.0164(2) Uani 1 1 d . . . . .
C6 C 0.24008(13) 0.72538(8) 0.50766(9) 0.0167(2) Uani 1 1 d . . . . .
C11 C 0.42998(15) 0.80748(8) 0.72732(10) 0.0198(3) Uani 1 1 d . . . . .
H11 H 0.484834 0.785412 0.781512 0.024 Uiso 1 1 calc R . . . .
C22 C 0.59425(15) 0.64110(8) 0.50029(10) 0.0195(3) Uani 1 1 d . . . . .
H22 H 0.508312 0.638888 0.456619 0.023 Uiso 1 1 calc R . . . .
C16 C 0.78499(15) 0.64788(8) 0.83489(10) 0.0207(3) Uani 1 1 d . . . . .
H16 H 0.884387 0.654207 0.824279 0.025 Uiso 1 1 calc R . . . .
C2 C 0.22471(14) 0.58191(8) 0.47037(10) 0.0201(3) Uani 1 1 d . . . . .
H2 H 0.242818 0.527162 0.487430 0.024 Uiso 1 1 calc R . . . .
C14 C 0.59894(17) 0.63639(8) 0.94216(10) 0.0232(3) Uani 1 1 d . . . . .
H14 H 0.573264 0.634416 1.004195 0.028 Uiso 1 1 calc R . . . .
C5 C 0.16756(14) 0.74444(9) 0.41703(10) 0.0220(3) Uani 1 1 d . . . . .
H5 H 0.148360 0.799011 0.399619 0.026 Uiso 1 1 calc R . . . .
C4 C 0.12461(15) 0.68165(10) 0.35351(10) 0.0260(3) Uani 1 1 d . . . . .
H4 H 0.077568 0.693872 0.292731 0.031 Uiso 1 1 calc R . . . .
C21 C 0.73103(16) 0.64558(8) 0.46610(11) 0.0227(3) Uani 1 1 d . . . . .
H21 H 0.737382 0.647063 0.400670 0.027 Uiso 1 1 calc R . . . .
C19 C 0.84596(15) 0.64546(8) 0.62755(11) 0.0213(3) Uani 1 1 d . . . . .
H19 H 0.931047 0.646085 0.672019 0.026 Uiso 1 1 calc R . . . .
C20 C 0.85882(16) 0.64783(8) 0.53106(11) 0.0239(3) Uani 1 1 d . . . . .
H20 H 0.952630 0.650924 0.509796 0.029 Uiso 1 1 calc R . . . .
C10 C 0.40985(15) 0.89190(8) 0.72207(11) 0.0230(3) Uani 1 1 d . . . . .
H10 H 0.452224 0.926077 0.770956 0.028 Uiso 1 1 calc R . . . .
C8 C 0.26579(16) 0.87188(8) 0.57073(11) 0.0227(3) Uani 1 1 d . . . . .
H8 H 0.207890 0.892877 0.517080 0.027 Uiso 1 1 calc R . . . .
C15 C 0.74736(16) 0.64599(8) 0.92696(10) 0.0234(3) Uani 1 1 d . . . . .
H15 H 0.821251 0.651141 0.978687 0.028 Uiso 1 1 calc R . . . .
C3 C 0.15165(15) 0.60037(9) 0.38040(10) 0.0244(3) Uani 1 1 d . . . . .
H3 H 0.120769 0.558074 0.338058 0.029 Uiso 1 1 calc R . . . .
C9 C 0.32551(16) 0.92414(8) 0.64266(11) 0.0253(3) Uani 1 1 d . . . . .
H9 H 0.308991 0.980600 0.637572 0.030 Uiso 1 1 calc R . . . .
C23 C 0.21137(19) 0.45589(10) 0.81184(15) 0.0399(4) Uani 1 1 d . . . . .
H23A H 0.305313 0.474781 0.845722 0.048 Uiso 1 1 calc R . . . .
H23B H 0.205529 0.475692 0.746498 0.048 Uiso 1 1 calc R . . . .


_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
Cl2 C23 1.7533(16) . ?
Si1 F1 1.6610(8) . ?
Si1 F2 1.6586(8) . ?
Si1 N2 2.1172(11) . ?
Si1 N1 2.0949(11) . ?
Si1 C12 1.9111(13) . ?
Si1 C1 1.9064(13) . ?
Cl1 C23 1.7528(17) . ?
N2 C18 1.3541(16) . ?
N2 C22 1.3404(17) . ?
N1 C7 1.3547(16) . ?
N1 C11 1.3370(17) . ?
C12 C13 1.3955(18) . ?
C12 C17 1.3947(18) . ?
C7 C6 1.4629(18) . ?
C7 C8 1.3908(17) . ?
C18 C17 1.4647(19) . ?
C18 C19 1.3898(18) . ?
C13 C14 1.3910(19) . ?
C1 C6 1.3966(17) . ?
C1 C2 1.3958(18) . ?
C17 C16 1.3978(18) . ?
C6 C5 1.3973(18) . ?
C11 C10 1.3834(18) . ?
C22 C21 1.3758(19) . ?
C16 C15 1.378(2) . ?
C2 C3 1.3890(19) . ?
C14 C15 1.387(2) . ?
C5 C4 1.381(2) . ?
C4 C3 1.386(2) . ?
C21 C20 1.383(2) . ?
C19 C20 1.378(2) . ?
C10 C9 1.378(2) . ?
C8 C9 1.380(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
F1 Si1 N2 89.43(4) . . ?
F1 Si1 N1 173.53(5) . . ?
F1 Si1 C12 94.53(5) . . ?
F1 Si1 C1 94.73(5) . . ?
F2 Si1 F1 96.19(4) . . ?
F2 Si1 N2 173.17(4) . . ?
F2 Si1 N1 88.94(4) . . ?
F2 Si1 C12 95.38(5) . . ?
F2 Si1 C1 95.35(5) . . ?
N1 Si1 N2 85.74(4) . . ?
C12 Si1 N2 80.25(5) . . ?
C12 Si1 N1 88.89(5) . . ?
C1 Si1 N2 88.03(5) . . ?
C1 Si1 N1 80.83(5) . . ?
C1 Si1 C12 164.98(6) . . ?
C18 N2 Si1 113.34(9) . . ?
C22 N2 Si1 127.69(9) . . ?
C22 N2 C18 118.87(11) . . ?
C7 N1 Si1 113.14(8) . . ?
C11 N1 Si1 127.53(9) . . ?
C11 N1 C7 119.12(11) . . ?
C13 C12 Si1 125.37(10) . . ?
C17 C12 Si1 117.55(10) . . ?
C17 C12 C13 117.07(12) . . ?
N1 C7 C6 113.65(11) . . ?
N1 C7 C8 120.62(12) . . ?
C8 C7 C6 125.73(12) . . ?
N2 C18 C17 113.38(11) . . ?
N2 C18 C19 121.03(12) . . ?
C19 C18 C17 125.59(12) . . ?
C14 C13 C12 121.63(13) . . ?
C6 C1 Si1 117.14(9) . . ?
C2 C1 Si1 125.25(10) . . ?
C2 C1 C6 117.58(12) . . ?
C12 C17 C18 115.39(11) . . ?
C12 C17 C16 121.76(12) . . ?
C16 C17 C18 122.84(12) . . ?
C1 C6 C7 114.96(11) . . ?
C1 C6 C5 121.57(12) . . ?
C5 C6 C7 123.44(12) . . ?
N1 C11 C10 122.76(13) . . ?
N2 C22 C21 122.71(13) . . ?
C15 C16 C17 119.77(13) . . ?
C3 C2 C1 121.15(13) . . ?
C15 C14 C13 120.00(13) . . ?
C4 C5 C6 119.51(13) . . ?
C5 C4 C3 119.95(13) . . ?
C22 C21 C20 118.61(13) . . ?
C20 C19 C18 119.36(13) . . ?
C19 C20 C21 119.41(13) . . ?
C9 C10 C11 118.41(13) . . ?
C9 C8 C7 119.66(13) . . ?
C16 C15 C14 119.76(13) . . ?
C4 C3 C2 120.22(13) . . ?
C10 C9 C8 119.40(12) . . ?
Cl1 C23 Cl2 111.87(9) . . ?

_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
;
####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1987501'
loop_
_audit_author_name
_audit_author_address
'Kohei Sekine'
;Kyushu University
Japan
;
_audit_update_record             
;
2020-03-02 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;
_audit_creation_date             2020-01-29
_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         'C26 H26 F2 N4 Si, C H2 Cl2'
_chemical_formula_sum            'C27 H28 Cl2 F2 N4 Si'
_chemical_formula_weight         545.52
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
Cl Cl 0.1484 0.1585 '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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.1097(4)
_cell_length_b                   10.9238(3)
_cell_length_c                   17.0344(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.326(3)
_cell_angle_gamma                90
_cell_volume                     2618.06(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21607
_cell_measurement_temperature    123
_cell_measurement_theta_max      30.9210
_cell_measurement_theta_min      1.8630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1704
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30027
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.217
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn70 area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50   16.00    --  -20.00  45.00   0.00  360
  2  ω   -110.00  70.00   0.50   16.00    --  -20.00  45.00  90.00  360
  3  ω   -110.00  70.00   0.50   16.00    --  -20.00  45.00 270.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0458862000
_diffrn_orient_matrix_UB_12      -0.0266073000
_diffrn_orient_matrix_UB_13      -0.0054607000
_diffrn_orient_matrix_UB_21      -0.0208702000
_diffrn_orient_matrix_UB_22      0.0577327000
_diffrn_orient_matrix_UB_23      0.0066810000
_diffrn_orient_matrix_UB_31      -0.0011590000
_diffrn_orient_matrix_UB_32      0.0130271000
_diffrn_orient_matrix_UB_33      -0.0408764000
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           16.0000
_diffrn_source_power             0.8000
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           50.0000
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5148
_reflns_number_total             5995
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.067
_refine_diff_density_min         -1.094
_refine_diff_density_rms         0.169
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5995
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0818
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1427P)²+2.0241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2105
_refine_ls_wR_factor_ref         0.2219
_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 Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C2(H2), C14(H14), C19(H19), C8(H8), C22(H22), C16(H16), C5(H5),
 C3(H3), C10(H10), C21(H21), C11(H11), C20(H20), C9(H9)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C24(H24A,H24B,
 H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.24979(4) 0.23053(5) 0.73684(4) 0.01413(19) Uani 1 1 d . . . . .
Cl2 Cl 0.29763(6) 0.71700(8) 0.72661(5) 0.0466(3) Uani 1 1 d . . . . .
Cl1 Cl 0.24966(11) 0.59978(12) 0.87328(6) 0.0814(5) Uani 1 1 d . . . . .
F1 F 0.31842(9) 0.34225(12) 0.70372(8) 0.0205(3) Uani 1 1 d . . . . .
F2 F 0.17560(9) 0.32211(13) 0.78232(8) 0.0208(3) Uani 1 1 d . . . . .
N2 N 0.34165(12) 0.09959(17) 0.69252(11) 0.0146(4) Uani 1 1 d . . . . .
N1 N 0.16507(12) 0.07922(17) 0.76336(11) 0.0153(4) Uani 1 1 d . . . . .
N4 N 0.54228(16) 0.1534(2) 1.01918(13) 0.0291(5) Uani 1 1 d . . . . .
N3 N -0.03879(16) 0.2058(2) 0.44494(14) 0.0298(5) Uani 1 1 d . . . . .
C1 C 0.16824(15) 0.2227(2) 0.64190(14) 0.0152(4) Uani 1 1 d . . . . .
C12 C 0.33113(14) 0.2015(2) 0.82967(13) 0.0154(4) Uani 1 1 d . . . . .
C6 C 0.09197(14) 0.1392(2) 0.63899(13) 0.0151(4) Uani 1 1 d . . . . .
C13 C 0.32077(16) 0.2509(2) 0.90464(14) 0.0183(5) Uani 1 1 d . . . . .
H13 H 0.266861 0.296806 0.912682 0.022 Uiso 1 1 calc R . . . .
C18 C 0.41683(15) 0.0709(2) 0.74400(13) 0.0155(4) Uani 1 1 d . . . . .
C17 C 0.41280(15) 0.13035(19) 0.82193(13) 0.0142(4) Uani 1 1 d . . . . .
C7 C 0.09067(15) 0.0590(2) 0.70888(13) 0.0158(4) Uani 1 1 d . . . . .
C2 C 0.17118(16) 0.3020(2) 0.57713(14) 0.0200(5) Uani 1 1 d . . . . .
H2 H 0.220091 0.359014 0.576774 0.024 Uiso 1 1 calc R . . . .
C14 C 0.38878(17) 0.2333(2) 0.96751(14) 0.0200(5) Uani 1 1 d . . . . .
H14 H 0.378392 0.265721 1.016600 0.024 Uiso 1 1 calc R . . . .
C19 C 0.48688(16) -0.0108(2) 0.72283(15) 0.0205(5) Uani 1 1 d . . . . .
H19 H 0.538465 -0.029089 0.758099 0.025 Uiso 1 1 calc R . . . .
C8 C 0.02188(16) -0.0290(2) 0.72226(15) 0.0225(5) Uani 1 1 d . . . . .
H8 H -0.029178 -0.041609 0.685360 0.027 Uiso 1 1 calc R . . . .
C22 C 0.33407(16) 0.0470(2) 0.62019(14) 0.0192(5) Uani 1 1 d . . . . .
H22 H 0.282307 0.066871 0.585489 0.023 Uiso 1 1 calc R . . . .
C16 C 0.48380(15) 0.1137(2) 0.88316(14) 0.0174(4) Uani 1 1 d . . . . .
H16 H 0.537723 0.067975 0.874863 0.021 Uiso 1 1 calc R . . . .
C5 C 0.02241(16) 0.1334(2) 0.57595(14) 0.0201(5) Uani 1 1 d . . . . .
H5 H -0.027024 0.077186 0.576920 0.024 Uiso 1 1 calc R . . . .
C3 C 0.10317(18) 0.2980(2) 0.51341(15) 0.0237(5) Uani 1 1 d . . . . .
H3 H 0.107724 0.352283 0.471809 0.028 Uiso 1 1 calc R . . . .
C10 C 0.10828(18) -0.0791(2) 0.84568(16) 0.0273(5) Uani 1 1 d . . . . .
H10 H 0.116425 -0.125675 0.891402 0.033 Uiso 1 1 calc R . . . .
C21 C 0.40126(17) -0.0358(2) 0.59609(15) 0.0229(5) Uani 1 1 d . . . . .
H21 H 0.394604 -0.071124 0.546303 0.028 Uiso 1 1 calc R . . . .
C15 C 0.47285(17) 0.1672(2) 0.95786(13) 0.0191(5) Uani 1 1 d . . . . .
C11 C 0.17334(16) 0.0113(2) 0.82933(14) 0.0207(5) Uani 1 1 d . . . . .
H11 H 0.224796 0.025398 0.865605 0.025 Uiso 1 1 calc R . . . .
C20 C 0.47870(18) -0.0642(2) 0.64865(16) 0.0249(5) Uani 1 1 d . . . . .
H20 H 0.524774 -0.118870 0.634072 0.030 Uiso 1 1 calc R . . . .
C9 C 0.03039(18) -0.0980(2) 0.79149(16) 0.0269(5) Uani 1 1 d . . . . .
H9 H -0.015458 -0.155974 0.801397 0.032 Uiso 1 1 calc R . . . .
C4 C 0.02727(17) 0.2128(2) 0.51078(14) 0.0206(5) Uani 1 1 d . . . . .
C23 C -0.13266(18) 0.1564(3) 0.45510(16) 0.0304(6) Uani 1 1 d . . . . .
H23A H -0.126628 0.075306 0.476691 0.046 Uiso 1 1 calc GR . . . .
H23B H -0.168657 0.153226 0.405017 0.046 Uiso 1 1 calc GR . . . .
H23C H -0.164731 0.207837 0.490307 0.046 Uiso 1 1 calc GR . . . .
C25 C 0.63757(19) 0.1132(3) 1.00288(17) 0.0307(6) Uani 1 1 d . . . . .
H25A H 0.636210 0.027724 0.989850 0.046 Uiso 1 1 calc GR . . . .
H25B H 0.680419 0.126363 1.048604 0.046 Uiso 1 1 calc GR . . . .
H25C H 0.658726 0.159247 0.959477 0.046 Uiso 1 1 calc GR . . . .
C26 C 0.5293(2) 0.2086(3) 1.09532(16) 0.0333(6) Uani 1 1 d . . . . .
H26A H 0.534431 0.296010 1.091276 0.050 Uiso 1 1 calc GR . . . .
H26B H 0.577241 0.178758 1.133517 0.050 Uiso 1 1 calc GR . . . .
H26C H 0.467577 0.187638 1.111403 0.050 Uiso 1 1 calc GR . . . .
C24 C -0.0366(2) 0.3014(3) 0.38545(19) 0.0407(7) Uani 1 1 d . . . . .
H24A H -0.056350 0.377633 0.407030 0.061 Uiso 1 1 calc GR . . . .
H24B H -0.078949 0.280066 0.340761 0.061 Uiso 1 1 calc GR . . . .
H24C H 0.026819 0.309453 0.369341 0.061 Uiso 1 1 calc GR . . . .
C27 C 0.2423(3) 0.5929(3) 0.7713(2) 0.0517(9) Uani 1 1 d . . . . .
H27A H 0.175796 0.590666 0.752130 0.062 Uiso 1 1 calc R . . . .
H27B H 0.271404 0.517347 0.755392 0.062 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 F1 1.6816(14) . ?
Si1 F2 1.6790(14) . ?
Si1 N2 2.1080(19) . ?
Si1 N1 2.1087(19) . ?
Si1 C1 1.915(2) . ?
Si1 C12 1.909(2) . ?
Cl2 C27 1.765(4) . ?
Cl1 C27 1.734(4) . ?
N2 C18 1.361(3) . ?
N2 C22 1.356(3) . ?
N1 C7 1.366(3) . ?
N1 C11 1.344(3) . ?
N4 C15 1.385(3) . ?
N4 C25 1.461(4) . ?
N4 C26 1.455(3) . ?
N3 C4 1.405(3) . ?
N3 C23 1.453(3) . ?
N3 C24 1.457(4) . ?
C1 C6 1.409(3) . ?
C1 C2 1.406(3) . ?
C12 C13 1.404(3) . ?
C12 C17 1.404(3) . ?
C6 C7 1.479(3) . ?
C6 C5 1.401(3) . ?
C13 C14 1.396(3) . ?
C18 C17 1.483(3) . ?
C18 C19 1.399(3) . ?
C17 C16 1.403(3) . ?
C7 C8 1.397(3) . ?
C2 C3 1.394(3) . ?
C14 C15 1.409(3) . ?
C19 C20 1.389(3) . ?
C8 C9 1.397(4) . ?
C22 C21 1.394(3) . ?
C16 C15 1.419(3) . ?
C5 C4 1.415(3) . ?
C3 C4 1.417(3) . ?
C10 C11 1.391(3) . ?
C10 C9 1.396(4) . ?
C21 C20 1.394(4) . ?

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
F1 Si1 N2 89.26(7) . . ?
F1 Si1 N1 172.23(8) . . ?
F1 Si1 C1 94.23(8) . . ?
F1 Si1 C12 94.19(8) . . ?
F2 Si1 F1 96.73(8) . . ?
F2 Si1 N2 172.37(8) . . ?
F2 Si1 N1 89.14(7) . . ?
F2 Si1 C1 93.47(8) . . ?
F2 Si1 C12 94.23(9) . . ?
N2 Si1 N1 85.33(7) . . ?
C1 Si1 N2 90.78(8) . . ?
C1 Si1 N1 80.30(8) . . ?
C12 Si1 N2 80.58(9) . . ?
C12 Si1 N1 90.42(8) . . ?
C12 Si1 C1 167.84(10) . . ?
C18 N2 Si1 113.32(14) . . ?
C22 N2 Si1 127.18(15) . . ?
C22 N2 C18 119.47(19) . . ?
C7 N1 Si1 113.59(14) . . ?
C11 N1 Si1 126.64(15) . . ?
C11 N1 C7 119.52(19) . . ?
C15 N4 C25 119.9(2) . . ?
C15 N4 C26 119.8(2) . . ?
C26 N4 C25 118.3(2) . . ?
C4 N3 C23 118.8(2) . . ?
C4 N3 C24 118.0(2) . . ?
C23 N3 C24 114.6(2) . . ?
C6 C1 Si1 117.87(16) . . ?
C2 C1 Si1 125.73(17) . . ?
C2 C1 C6 116.0(2) . . ?
C13 C12 Si1 126.30(17) . . ?
C17 C12 Si1 117.43(16) . . ?
C17 C12 C13 116.1(2) . . ?
C1 C6 C7 114.26(19) . . ?
C5 C6 C1 123.1(2) . . ?
C5 C6 C7 122.7(2) . . ?
C14 C13 C12 122.1(2) . . ?
N2 C18 C17 113.29(18) . . ?
N2 C18 C19 120.8(2) . . ?
C19 C18 C17 125.9(2) . . ?
C12 C17 C18 114.43(19) . . ?
C16 C17 C12 123.2(2) . . ?
C16 C17 C18 122.39(19) . . ?
N1 C7 C6 113.31(18) . . ?
N1 C7 C8 120.5(2) . . ?
C8 C7 C6 126.1(2) . . ?
C3 C2 C1 122.2(2) . . ?
C13 C14 C15 121.1(2) . . ?
C20 C19 C18 119.4(2) . . ?
C9 C8 C7 119.5(2) . . ?
N2 C22 C21 122.2(2) . . ?
C17 C16 C15 119.6(2) . . ?
C6 C5 C4 120.1(2) . . ?
C2 C3 C4 121.3(2) . . ?
C11 C10 C9 118.1(2) . . ?
C22 C21 C20 118.2(2) . . ?
N4 C15 C14 121.4(2) . . ?
N4 C15 C16 120.8(2) . . ?
C14 C15 C16 117.7(2) . . ?
N1 C11 C10 122.8(2) . . ?
C19 C20 C21 119.9(2) . . ?
C10 C9 C8 119.5(2) . . ?
N3 C4 C5 121.6(2) . . ?
N3 C4 C3 121.0(2) . . ?
C5 C4 C3 117.3(2) . . ?
Cl1 C27 Cl2 113.8(2) . . ?

_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 1.333
_oxdiff_exptl_absorpt_empirical_full_min 0.731
####################################################################### 
# 
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 1987500'
loop_
_audit_author_name
_audit_author_address
'Kohei Sekine'
;Kyushu University
Japan
;
_audit_update_record             
;
2020-03-02 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;
_audit_creation_date             2020-01-29
_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         'C24 H14 F8 N2 Si'
_chemical_formula_sum            'C24 H14 F8 N2 Si'
_chemical_formula_weight         510.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
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      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                   7.8983(2)
_cell_length_b                   10.1395(3)
_cell_length_c                   14.2203(4)
_cell_angle_alpha                80.924(2)
_cell_angle_beta                 74.043(2)
_cell_angle_gamma                85.365(2)
_cell_volume                     1080.40(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10917
_cell_measurement_temperature    113
_cell_measurement_theta_max      31.0320
_cell_measurement_theta_min      2.3480
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.569
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15251
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.036
_diffrn_ambient_temperature      113.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn70 area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50   16.00    --  -20.00  45.00   0.00  360
  2  ω   -110.00  70.00   0.50   16.00    --  -20.00  45.00 270.00  360
  3  ω   -110.00  70.00   0.50   16.00    --  -20.00  45.00 180.00  360
  4  ω   -110.00 -20.00   0.50   16.00    --  -20.00  45.00  90.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0454821000
_diffrn_orient_matrix_UB_12      0.0617477000
_diffrn_orient_matrix_UB_13      -0.0095425000
_diffrn_orient_matrix_UB_21      0.0511822000
_diffrn_orient_matrix_UB_22      0.0316357000
_diffrn_orient_matrix_UB_23      0.0232196000
_diffrn_orient_matrix_UB_31      0.0636355000
_diffrn_orient_matrix_UB_32      0.0145825000
_diffrn_orient_matrix_UB_33      -0.0460011000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4339
_reflns_number_total             4932
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4932
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.067
_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)+(0.0640P)²+0.6158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1202
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F3-C23B \\sim F3-C23A
 with sigma of 0.02
 C4-C23B \\sim C4-C23A
 with sigma of 0.02
 F4A-C23B \\sim F4B-C23A
 with sigma of 0.02
 C23B-F5A \\sim C23A-F5B
 with sigma of 0.02
 F3-F4A \\sim F3-F4B
 with sigma of 0.04
 F3-F5A \\sim F3-F5B
 with sigma of 0.04
 C4-F4A \\sim C4-F4B
 with sigma of 0.04
 C4-F5A \\sim C4-F5B
 with sigma of 0.04
 F4A-F5A \\sim F4B-F5B
 with sigma of 0.04
3. Rigid bond restraints
 C23A, C23B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C23A \\sim C23B: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
5. Others
 Sof(C23A)=Sof(F5B)=Sof(F4B)=1-FVAR(1)
 Sof(F4A)=Sof(C23B)=Sof(F5A)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C22(H22), C19(H19), C16(H16), C14(H14), C8(H8), C2(H2),
 C10(H10), C20(H20), C9(H9), C5(H5), C21(H21), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Si01 Si 0.19278(5) 0.48626(4) 0.24512(3) 0.01446(12) Uani 1 1 d . . . . .
F2 F 0.17341(12) 0.37213(9) 0.17708(7) 0.0182(2) Uani 1 1 d . . . . .
F1 F -0.02015(12) 0.52558(10) 0.28562(7) 0.0205(2) Uani 1 1 d . . . . .
F6 F 0.32813(17) 0.00967(12) 0.61243(9) 0.0378(3) Uani 1 1 d . . . . .
F7 F 0.2142(2) 0.16189(12) 0.70041(8) 0.0432(3) Uani 1 1 d . . . . .
F8 F 0.04873(19) 0.02975(16) 0.66637(11) 0.0566(4) Uani 1 1 d . . . . .
N1 N 0.46393(17) 0.46347(13) 0.19652(9) 0.0143(3) Uani 1 1 d . . . . .
N2 N 0.25259(17) 0.61433(13) 0.33431(10) 0.0159(3) Uani 1 1 d . . . . .
F3 F 0.3215(3) 1.05910(13) -0.08379(12) 0.0672(5) Uani 1 1 d D . . . .
C18 C 0.24984(19) 0.55370(15) 0.42646(11) 0.0158(3) Uani 1 1 d . . . . .
C17 C 0.21512(19) 0.41016(15) 0.44214(11) 0.0153(3) Uani 1 1 d . . . . .
C7 C 0.5370(2) 0.54999(15) 0.11568(11) 0.0155(3) Uani 1 1 d . . . . .
C11 C 0.5684(2) 0.37346(16) 0.23605(12) 0.0181(3) Uani 1 1 d . . . . .
H11 H 0.515714 0.311443 0.291909 0.022 Uiso 1 1 calc R . . . .
C12 C 0.19235(19) 0.36087(15) 0.36053(11) 0.0157(3) Uani 1 1 d . . . . .
C13 C 0.1647(2) 0.22449(16) 0.37018(12) 0.0186(3) Uani 1 1 d . . . . .
H13 H 0.146554 0.188511 0.316095 0.022 Uiso 1 1 calc R . . . .
C6 C 0.4078(2) 0.64377(15) 0.08070(11) 0.0168(3) Uani 1 1 d . . . . .
C1 C 0.2339(2) 0.62856(16) 0.13787(12) 0.0172(3) Uani 1 1 d . . . . .
C22 C 0.2915(2) 0.74369(16) 0.30929(13) 0.0202(3) Uani 1 1 d . . . . .
H22 H 0.292004 0.786180 0.244707 0.024 Uiso 1 1 calc R . . . .
C19 C 0.2813(2) 0.62369(17) 0.49575(13) 0.0220(3) Uani 1 1 d . . . . .
H19 H 0.274050 0.580827 0.561074 0.026 Uiso 1 1 calc R . . . .
C15 C 0.1882(2) 0.19292(16) 0.53735(12) 0.0192(3) Uani 1 1 d . . . . .
C16 C 0.2131(2) 0.32800(16) 0.53107(12) 0.0181(3) Uani 1 1 d . . . . .
H16 H 0.228365 0.363906 0.585854 0.022 Uiso 1 1 calc R . . . .
C14 C 0.1633(2) 0.14099(16) 0.45730(13) 0.0210(3) Uani 1 1 d . . . . .
H14 H 0.145315 0.048302 0.462515 0.025 Uiso 1 1 calc R . . . .
C8 C 0.7178(2) 0.54777(18) 0.07376(12) 0.0214(3) Uani 1 1 d . . . . .
H8 H 0.767715 0.608291 0.016347 0.026 Uiso 1 1 calc R . . . .
C2 C 0.1049(2) 0.71766(17) 0.11079(13) 0.0231(4) Uani 1 1 d . . . . .
H2 H -0.014711 0.709582 0.147865 0.028 Uiso 1 1 calc R . . . .
C10 C 0.7487(2) 0.36738(18) 0.19893(13) 0.0218(3) Uani 1 1 d . . . . .
H10 H 0.819582 0.303559 0.229138 0.026 Uiso 1 1 calc R . . . .
C20 C 0.3234(2) 0.75647(18) 0.46885(14) 0.0255(4) Uani 1 1 d . . . . .
H20 H 0.347187 0.805490 0.515184 0.031 Uiso 1 1 calc R . . . .
C9 C 0.8244(2) 0.45669(19) 0.11635(13) 0.0240(4) Uani 1 1 d . . . . .
H9 H 0.948633 0.455235 0.089298 0.029 Uiso 1 1 calc R . . . .
C5 C 0.4546(2) 0.74307(17) -0.00069(12) 0.0226(3) Uani 1 1 d . . . . .
H5 H 0.573621 0.750675 -0.038962 0.027 Uiso 1 1 calc R . . . .
C21 C 0.3307(2) 0.81733(17) 0.37354(13) 0.0239(4) Uani 1 1 d . . . . .
H21 H 0.361951 0.907918 0.352973 0.029 Uiso 1 1 calc R . . . .
C24 C 0.1933(2) 0.10038(17) 0.62923(13) 0.0247(4) Uani 1 1 d . . . . .
C4 C 0.3237(3) 0.83009(18) -0.02428(13) 0.0282(4) Uani 1 1 d D . . . .
C3 C 0.1494(3) 0.81754(19) 0.03061(14) 0.0293(4) Uani 1 1 d . . . . .
H3 H 0.060456 0.877449 0.013207 0.035 Uiso 1 1 calc R . . . .
F4A F 0.2367(9) 0.9418(5) -0.1627(4) 0.0606(14) Uani 0.528(13) 1 d D . P A 1
C23B C 0.3540(13) 0.9412(7) -0.1117(5) 0.0286(18) Uani 0.528(13) 1 d D U P A 1
F5A F 0.5097(7) 0.9200(6) -0.1719(3) 0.062(2) Uani 0.528(13) 1 d D . P A 1
C23A C 0.3890(16) 0.9398(10) -0.1058(8) 0.046(3) Uani 0.472(13) 1 d D U P A 2
F5B F 0.5571(5) 0.9738(7) -0.1313(6) 0.067(2) Uani 0.472(13) 1 d D . P A 2
F4B F 0.3516(17) 0.9259(4) -0.1891(4) 0.076(4) Uani 0.472(13) 1 d D . 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
Si01 F2 1.6619(10) . ?
Si01 F1 1.6585(10) . ?
Si01 N1 2.0674(13) . ?
Si01 N2 2.1133(14) . ?
Si01 C12 1.9103(16) . ?
Si01 C1 1.9033(17) . ?
F6 C24 1.345(2) . ?
F7 C24 1.322(2) . ?
F8 C24 1.333(2) . ?
N1 C7 1.350(2) . ?
N1 C11 1.342(2) . ?
N2 C18 1.352(2) . ?
N2 C22 1.341(2) . ?
F3 C23B 1.302(8) . ?
F3 C23A 1.330(11) . ?
C18 C17 1.474(2) . ?
C18 C19 1.386(2) . ?
C17 C12 1.393(2) . ?
C17 C16 1.397(2) . ?
C7 C6 1.472(2) . ?
C7 C8 1.388(2) . ?
C11 C10 1.376(2) . ?
C12 C13 1.397(2) . ?
C13 C14 1.384(2) . ?
C6 C1 1.398(2) . ?
C6 C5 1.395(2) . ?
C1 C2 1.400(2) . ?
C22 C21 1.377(2) . ?
C19 C20 1.382(2) . ?
C15 C16 1.385(2) . ?
C15 C14 1.393(2) . ?
C15 C24 1.492(2) . ?
C8 C9 1.381(2) . ?
C2 C3 1.386(3) . ?
C10 C9 1.387(2) . ?
C20 C21 1.386(3) . ?
C5 C4 1.382(3) . ?
C4 C3 1.389(3) . ?
C4 C23B 1.519(6) . ?
C4 C23A 1.485(10) . ?
F4A C23B 1.325(10) . ?
C23B F5A 1.314(8) . ?
C23A F5B 1.334(11) . ?
C23A F4B 1.328(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
F2 Si01 N1 89.47(5) . . ?
F2 Si01 N2 171.23(5) . . ?
F2 Si01 C12 94.95(6) . . ?
F2 Si01 C1 94.63(6) . . ?
F1 Si01 F2 97.34(5) . . ?
F1 Si01 N1 172.24(5) . . ?
F1 Si01 N2 90.35(5) . . ?
F1 Si01 C12 92.81(6) . . ?
F1 Si01 C1 94.41(6) . . ?
N1 Si01 N2 83.16(5) . . ?
C12 Si01 N1 90.32(6) . . ?
C12 Si01 N2 80.39(6) . . ?
C1 Si01 N1 81.26(6) . . ?
C1 Si01 N2 88.96(6) . . ?
C1 Si01 C12 167.17(7) . . ?
C7 N1 Si01 113.86(10) . . ?
C11 N1 Si01 126.98(11) . . ?
C11 N1 C7 119.15(13) . . ?
C18 N2 Si01 113.42(10) . . ?
C22 N2 Si01 127.61(11) . . ?
C22 N2 C18 118.97(14) . . ?
N2 C18 C17 113.25(13) . . ?
N2 C18 C19 121.21(14) . . ?
C19 C18 C17 125.53(15) . . ?
C12 C17 C18 115.24(14) . . ?
C12 C17 C16 122.30(14) . . ?
C16 C17 C18 122.40(14) . . ?
N1 C7 C6 113.45(13) . . ?
N1 C7 C8 121.03(15) . . ?
C8 C7 C6 125.50(14) . . ?
N1 C11 C10 122.65(15) . . ?
C17 C12 Si01 117.45(12) . . ?
C17 C12 C13 117.72(15) . . ?
C13 C12 Si01 124.79(12) . . ?
C14 C13 C12 121.01(15) . . ?
C1 C6 C7 114.48(14) . . ?
C5 C6 C7 123.14(15) . . ?
C5 C6 C1 122.35(15) . . ?
C6 C1 Si01 116.86(12) . . ?
C6 C1 C2 117.47(15) . . ?
C2 C1 Si01 125.66(13) . . ?
N2 C22 C21 122.59(16) . . ?
C20 C19 C18 119.33(16) . . ?
C16 C15 C14 120.65(15) . . ?
C16 C15 C24 120.20(15) . . ?
C14 C15 C24 119.12(15) . . ?
C15 C16 C17 118.34(15) . . ?
C13 C14 C15 119.96(15) . . ?
C9 C8 C7 119.32(15) . . ?
C3 C2 C1 120.92(17) . . ?
C11 C10 C9 118.36(15) . . ?
C19 C20 C21 119.25(16) . . ?
C8 C9 C10 119.46(15) . . ?
C4 C5 C6 118.39(16) . . ?
C22 C21 C20 118.58(16) . . ?
F6 C24 C15 111.52(14) . . ?
F7 C24 F6 105.75(15) . . ?
F7 C24 F8 107.30(16) . . ?
F7 C24 C15 113.39(14) . . ?
F8 C24 F6 105.54(15) . . ?
F8 C24 C15 112.78(15) . . ?
C5 C4 C3 120.81(16) . . ?
C5 C4 C23B 124.4(4) . . ?
C5 C4 C23A 114.2(5) . . ?
C3 C4 C23B 114.8(4) . . ?
C3 C4 C23A 124.8(5) . . ?
C2 C3 C4 120.05(17) . . ?
F3 C23B C4 112.0(5) . . ?
F3 C23B F4A 100.6(6) . . ?
F3 C23B F5A 116.7(6) . . ?
F4A C23B C4 111.6(5) . . ?
F5A C23B C4 108.6(6) . . ?
F5A C23B F4A 106.9(6) . . ?
F3 C23A C4 112.6(7) . . ?
F3 C23A F5B 95.7(7) . . ?
F5B C23A C4 121.0(8) . . ?
F4B C23A F3 106.1(8) . . ?
F4B C23A C4 113.1(8) . . ?
F4B C23A F5B 106.2(8) . . ?

_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 2.130
_oxdiff_exptl_absorpt_empirical_full_min 0.721
