# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_cu_1109_9_0m
_database_code_depnum_ccdc_archive 'CCDC 2050566'
loop_
_audit_author_name
_audit_author_address
'XIAYU ZHANG'
;Hunan University of Technology
China
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2021-07-18 downloaded from the CCDC.
;
_audit_creation_date             2020-11-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         '0.04(C22 H14 F2)'
_chemical_formula_sum            'C0.967 H0.615 F0.088'
_chemical_formula_weight         13.91
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_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.07536 0.05506 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   9.6755(3)
_cell_length_b                   10.4719(3)
_cell_length_c                   17.0175(5)
_cell_angle_alpha                97.5810(10)
_cell_angle_beta                 103.5160(10)
_cell_angle_gamma                95.6220(10)
_cell_volume                     1646.92(9)
_cell_formula_units_Z            91
_cell_measurement_reflns_used    9838
_cell_measurement_temperature    150
_cell_measurement_theta_max      74.65
_cell_measurement_theta_min      4.37
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_T_max  0.0872
_exptl_absorpt_correction_T_min  0.0110
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.2758
_exptl_crystal_description       plate
_exptl_crystal_F_000             658.2153
_diffrn_reflns_av_R_equivalents  0.1374
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30043
_diffrn_reflns_theta_full        74.6134
_diffrn_reflns_theta_max         74.61
_diffrn_reflns_theta_min         2.71
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.9889
_diffrn_measured_fraction_theta_max 0.9889
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              12
_reflns_limit_k_min              -13
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                5909
_reflns_number_total             6662
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.2381
_refine_diff_density_min         -0.2651
_refine_diff_density_rms         0.0485
_refine_ls_d_res_high            0.7995
_refine_ls_d_res_low             16.3330
_refine_ls_goodness_of_fit_ref   1.0510
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    56
_refine_ls_number_parameters     433
_refine_ls_number_reflns         6662
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.0510
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0552P)²+0.3271P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1312
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C40(H40), C38(H38), C20(H20), C16(H16), C3(H3), C12(H12), C36(H36),
 C14(H14), C9(H9), C5(H5), C33(H33), C18(H18), C26(H26), C30(H30), C31(H31),
 C39(H39), C27(H27), C24(H24), C4(H4), C17(H17), C25(H25), C32(H32), C2(H2),
 C41(H41), C10(H10)
2.b :
 C44(H44), C22(H22)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
F3 F 0.22365(9) 0.75514(9) 0.45886(6) 0.0456(2) Uani 1.000000 .
F2 F 0.55840(11) 0.46562(10) 0.36010(5) 0.0527(3) Uani 1.000000 .
F1 F -0.10942(10) 0.36101(12) -0.17555(6) 0.0577(3) Uani 1.000000 .
F4 F 1.10597(12) 0.40614(9) 0.64212(7) 0.0578(3) Uani 1.000000 .
C8 C 0.45549(13) 0.34120(13) 0.11124(7) 0.0275(3) Uani 1.000000 .
C13 C 0.50113(14) 0.25696(13) 0.16616(8) 0.0310(3) Uani 1.000000 .
H13 H 0.50813(14) 0.16963(13) 0.14557(8) 0.0372(3) Uiso 1.000000 R
C34 C 0.89324(14) 0.72452(13) 0.60914(8) 0.0306(3) Uani 1.000000 .
C28 C 0.65951(14) 0.81608(13) 0.56353(8) 0.0306(3) Uani 1.000000 .
C6 C 0.28329(14) 0.31437(12) -0.03038(8) 0.0290(3) Uani 1.000000 .
C40 C 1.25864(15) 0.99171(14) 0.75244(8) 0.0338(3) Uani 1.000000 .
H40 H 1.30661(15) 0.95457(14) 0.79750(8) 0.0405(3) Uiso 1.000000 R
C7 C 0.42351(13) 0.29377(12) 0.02127(8) 0.0285(3) Uani 1.000000 .
C38 C 1.11532(15) 0.95053(14) 0.71659(8) 0.0340(3) Uani 1.000000 .
H38 H 1.06624(15) 0.88414(14) 0.73683(8) 0.0408(4) Uiso 1.000000 R
C20 C 0.89289(14) 0.27303(14) 0.12206(8) 0.0339(3) Uani 1.000000 .
H20 H 0.95751(14) 0.33791(14) 0.16145(8) 0.0406(4) Uiso 1.000000 R
C16 C 0.75867(14) 0.30018(13) 0.08525(8) 0.0323(3) Uani 1.000000 .
H16 H 0.73226(14) 0.38358(13) 0.09930(8) 0.0388(3) Uiso 1.000000 R
C37 C 1.04044(15) 1.00462(13) 0.65085(8) 0.0316(3) Uani 1.000000 .
C35 C 0.81742(15) 0.84040(13) 0.59729(8) 0.0309(3) Uani 1.000000 .
C3 C 0.16445(15) 0.32734(14) 0.00248(8) 0.0349(3) Uani 1.000000 .
H3 H 0.17468(15) 0.32602(14) 0.05925(8) 0.0419(4) Uiso 1.000000 R
C12 C 0.53655(15) 0.29798(15) 0.25030(8) 0.0351(3) Uani 1.000000 .
H12 H 0.56841(15) 0.24049(15) 0.28743(8) 0.0422(4) Uiso 1.000000 R
C36 C 0.88737(15) 0.96223(13) 0.61208(8) 0.0334(3) Uani 1.000000 .
H36 H 0.83147(15) 1.02823(13) 0.59559(8) 0.0401(3) Uiso 1.000000 R
C14 C 0.51447(14) 0.22860(13) -0.01234(8) 0.0321(3) Uani 1.000000 .
H14 H 0.47999(14) 0.19284(13) -0.06870(8) 0.0385(3) Uiso 1.000000 R
C9 C 0.44123(15) 0.46761(14) 0.14231(8) 0.0345(3) Uani 1.000000 .
H9 H 0.40761(15) 0.52540(14) 0.10575(8) 0.0414(4) Uiso 1.000000 R
C15 C 0.66028(14) 0.20579(13) 0.02710(8) 0.0307(3) Uani 1.000000 .
C42 C 1.33396(15) 1.08776(13) 0.72295(8) 0.0313(3) Uani 1.000000 .
C5 C 0.26403(15) 0.31793(14) -0.11421(8) 0.0336(3) Uani 1.000000 .
H5 H 0.34332(15) 0.31037(14) -0.13776(8) 0.0403(3) Uiso 1.000000 R
C33 C 1.01171(15) 0.70670(14) 0.57712(8) 0.0344(3) Uani 1.000000 .
H33 H 1.04316(15) 0.76900(14) 0.54703(8) 0.0413(4) Uiso 1.000000 R
C18 C 0.84003(15) 0.05855(14) 0.04275(9) 0.0367(3) Uani 1.000000 .
H18 H 0.86738(15) -0.02409(14) 0.02773(9) 0.0440(4) Uiso 1.000000 R
C26 C 0.42322(16) 0.88243(15) 0.55267(9) 0.0377(3) Uani 1.000000 .
H26 H 0.36302(16) 0.94159(15) 0.56913(9) 0.0453(4) Uiso 1.000000 R
C30 C 0.91870(18) 0.52322(14) 0.66353(9) 0.0413(3) Uani 1.000000 .
H30 H 0.88737(18) 0.45955(14) 0.69277(9) 0.0495(4) Uiso 1.000000 R
C31 C 0.84714(15) 0.63042(14) 0.65187(8) 0.0353(3) Uani 1.000000 .
H31 H 0.76572(15) 0.63997(14) 0.67323(8) 0.0424(4) Uiso 1.000000 R
C39 C 1.11546(17) 1.10441(13) 0.62407(9) 0.0370(3) Uani 1.000000 .
H39 H 1.06620(17) 1.14525(13) 0.58118(9) 0.0444(4) Uiso 1.000000 R
C27 C 0.56991(16) 0.90263(14) 0.58706(8) 0.0354(3) Uani 1.000000 .
H27 H 0.61036(16) 0.97680(14) 0.62744(8) 0.0424(4) Uiso 1.000000 R
C24 C 0.45023(15) 0.68478(14) 0.47008(9) 0.0361(3) Uani 1.000000 .
H24 H 0.40830(15) 0.61025(14) 0.43028(9) 0.0433(4) Uiso 1.000000 R
C4 C 0.13302(16) 0.33210(15) -0.16357(9) 0.0396(3) Uani 1.000000 .
H4 H 0.12120(16) 0.33318(15) -0.22048(9) 0.0476(4) Uiso 1.000000 R
C17 C 0.70635(15) 0.08669(14) 0.00578(8) 0.0364(3) Uani 1.000000 .
H17 H 0.64361(15) 0.02315(14) -0.03547(8) 0.0437(4) Uiso 1.000000 R
C23 C 0.36694(15) 0.77459(14) 0.49411(9) 0.0348(3) Uani 1.000000 .
C11 C 0.52391(15) 0.42447(15) 0.27787(8) 0.0369(3) Uani 1.000000 .
C25 C 0.59639(15) 0.70587(13) 0.50535(8) 0.0336(3) Uani 1.000000 .
H25 H 0.65504(15) 0.64445(13) 0.48980(8) 0.0403(3) Uiso 1.000000 R
C21 C 1.07346(15) 0.12255(15) 0.14337(9) 0.0374(3) Uani 1.000000 .
C19 C 0.93553(14) 0.15161(14) 0.10242(8) 0.0322(3) Uani 1.000000 .
C32 C 1.08427(17) 0.60035(15) 0.58825(9) 0.0394(3) Uani 1.000000 .
H32 H 1.16500(17) 0.58915(15) 0.56649(9) 0.0473(4) Uiso 1.000000 R
C2 C 0.03257(15) 0.34203(16) -0.04604(10) 0.0404(3) Uani 1.000000 .
H2 H -0.04753(15) 0.35014(16) -0.02328(10) 0.0485(4) Uiso 1.000000 R
C41 C 1.25975(16) 1.14475(13) 0.65875(9) 0.0365(3) Uani 1.000000 .
H41 H 1.30881(16) 1.21159(13) 0.63886(9) 0.0438(4) Uiso 1.000000 R
C43 C 1.48440(16) 1.12649(14) 0.75869(9) 0.0366(3) Uani 1.000000 .
C10 C 0.47568(16) 0.51025(15) 0.22636(9) 0.0393(3) Uani 1.000000 .
H10 H 0.46613(16) 0.59656(15) 0.24767(9) 0.0472(4) Uiso 1.000000 R
C29 C 1.03599(17) 0.51120(14) 0.63180(9) 0.0406(3) Uani 1.000000 .
C1 C 0.01997(15) 0.34464(16) -0.12801(9) 0.0399(3) Uani 1.000000 .
C44 C 1.60840(18) 1.15821(17) 0.78826(11) 0.0481(4) Uani 1.000000 .
H44 H 1.70801(18) 1.18369(17) 0.81201(11) 0.0577(5) Uiso 1.000000 R
C22 C 1.18595(17) 0.09935(18) 0.17962(10) 0.0463(4) Uani 1.000000 .
H22 H 1.27621(17) 0.08073(18) 0.20871(10) 0.0555(4) Uiso 1.000000 R


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
F3 C23 1.3591(16) . ?
F2 C11 1.3601(14) . ?
F1 C1 1.3625(16) . ?
F4 C29 1.3569(17) . ?
C8 C13 1.3955(18) . ?
C8 C7 1.4947(16) . ?
C8 C9 1.3915(19) . ?
C13 C12 1.3898(18) . ?
C34 C35 1.4904(19) . ?
C34 C33 1.3974(19) . ?
C34 C31 1.3977(19) . ?
C28 C35 1.4846(18) . ?
C28 C27 1.3977(19) . ?
C28 C25 1.4011(19) . ?
C6 C7 1.4865(18) . ?
C6 C3 1.4016(18) . ?
C6 C5 1.4008(18) . ?
C40 C38 1.3781(19) . ?
C40 C42 1.3983(19) . ?
C7 C14 1.3482(19) . ?
C38 C37 1.4021(18) . ?
C20 C16 1.378(2) . ?
C20 C19 1.398(2) . ?
C16 C15 1.4070(18) . ?
C37 C36 1.4707(18) . ?
C37 C39 1.3994(19) . ?
C35 C36 1.347(2) . ?
C3 C2 1.383(2) . ?
C12 C11 1.373(2) . ?
C14 C15 1.4709(19) . ?
C9 C10 1.3914(19) . ?
C15 C17 1.397(2) . ?
C42 C41 1.3980(19) . ?
C42 C43 1.4348(19) . ?
C5 C4 1.381(2) . ?
C33 C32 1.384(2) . ?
C18 C17 1.378(2) . ?
C18 C19 1.399(2) . ?
C26 C27 1.386(2) . ?
C26 C23 1.376(2) . ?
C30 C31 1.388(2) . ?
C30 C29 1.375(2) . ?
C39 C41 1.382(2) . ?
C24 C23 1.379(2) . ?
C24 C25 1.3842(19) . ?
C4 C1 1.377(2) . ?
C11 C10 1.375(2) . ?
C21 C19 1.435(2) . ?
C21 C22 1.184(2) . ?
C32 C29 1.378(2) . ?
C2 C1 1.376(2) . ?
C43 C44 1.183(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
C7 C8 C13 119.46(12) . . ?
C9 C8 C13 118.61(12) . . ?
C9 C8 C7 121.92(12) . . ?
C12 C13 C8 121.47(13) . . ?
C33 C34 C35 120.73(12) . . ?
C31 C34 C35 120.98(12) . . ?
C31 C34 C33 118.29(13) . . ?
C27 C28 C35 121.57(12) . . ?
C25 C28 C35 120.36(12) . . ?
C25 C28 C27 118.05(13) . . ?
C3 C6 C7 121.25(11) . . ?
C5 C6 C7 121.18(11) . . ?
C5 C6 C3 117.54(12) . . ?
C42 C40 C38 120.46(13) . . ?
C6 C7 C8 117.79(11) . . ?
C14 C7 C8 121.83(12) . . ?
C14 C7 C6 120.30(11) . . ?
C37 C38 C40 121.35(12) . . ?
C19 C20 C16 121.10(12) . . ?
C15 C16 C20 120.76(13) . . ?
C36 C37 C38 122.08(12) . . ?
C39 C37 C38 117.65(13) . . ?
C39 C37 C36 120.25(12) . . ?
C28 C35 C34 117.03(11) . . ?
C36 C35 C34 122.56(13) . . ?
C36 C35 C28 120.32(12) . . ?
C2 C3 C6 121.36(13) . . ?
C11 C12 C13 117.68(13) . . ?
C35 C36 C37 127.38(13) . . ?
C15 C14 C7 128.28(12) . . ?
C10 C9 C8 120.69(13) . . ?
C14 C15 C16 122.92(12) . . ?
C17 C15 C16 117.47(13) . . ?
C17 C15 C14 119.60(12) . . ?
C41 C42 C40 118.73(13) . . ?
C43 C42 C40 120.04(13) . . ?
C43 C42 C41 121.23(13) . . ?
C4 C5 C6 121.83(13) . . ?
C32 C33 C34 121.50(13) . . ?
C19 C18 C17 120.05(13) . . ?
C23 C26 C27 118.37(13) . . ?
C29 C30 C31 118.52(14) . . ?
C30 C31 C34 120.90(14) . . ?
C41 C39 C37 121.33(13) . . ?
C26 C27 C28 121.34(13) . . ?
C25 C24 C23 118.40(13) . . ?
C1 C4 C5 118.15(13) . . ?
C18 C17 C15 122.01(13) . . ?
C26 C23 F3 118.87(12) . . ?
C24 C23 F3 118.59(12) . . ?
C24 C23 C26 122.54(13) . . ?
C12 C11 F2 118.15(14) . . ?
C10 C11 F2 118.75(13) . . ?
C10 C11 C12 123.09(12) . . ?
C24 C25 C28 121.27(13) . . ?
C22 C21 C19 177.75(15) . . ?
C18 C19 C20 118.52(13) . . ?
C21 C19 C20 120.68(13) . . ?
C21 C19 C18 120.79(13) . . ?
C29 C32 C33 118.04(14) . . ?
C1 C2 C3 118.52(13) . . ?
C39 C41 C42 120.39(13) . . ?
C44 C43 C42 179.85(17) . . ?
C11 C10 C9 118.41(13) . . ?
C30 C29 F4 119.05(14) . . ?
C32 C29 F4 118.21(14) . . ?
C32 C29 C30 122.74(14) . . ?
C4 C1 F1 118.91(13) . . ?
C2 C1 F1 118.51(13) . . ?
C2 C1 C4 122.58(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cu_1109_10_0m
_database_code_depnum_ccdc_archive 'CCDC 2050567'
loop_
_audit_author_name
_audit_author_address
'XIAYU ZHANG'
;Hunan University of Technology
China
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2021-07-18 downloaded from the CCDC.
;
_audit_creation_date             2020-11-28
_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         '0.03(C25 H22 F2 Si)'
_chemical_formula_sum            'C0.85 H0.75 F0.07 Si0.03'
_chemical_formula_weight         13.17
_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'
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      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                   9.2475(4)
_cell_length_b                   11.3110(4)
_cell_length_c                   20.2758(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.685(2)
_cell_angle_gamma                90
_cell_volume                     2118.49(14)
_cell_formula_units_Z            118
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.65
_cell_measurement_theta_min      4.37
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.176
_exptl_absorpt_correction_T_max  0.0872
_exptl_absorpt_correction_T_min  0.0107
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1098 before and 0.0535 after correction. The Ratio of minimum to maximum transmission is 0.1227. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1479
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            26712
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.644
_diffrn_reflns_theta_min         4.366
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3937
_reflns_number_total             4325
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 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         0.397
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.025
_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)+(0.0630P)²+0.5891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1295
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C15(H15), C9(H9), C18(H18), C17(H17), C16(H16), C4(H4), C12(H12),
 C5(H5), C3(H3), C2(H2), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C22(H22a,H22b,H22c), C23(H23a,H23b,H23c), C24(H24a,H24b,H24c)
;
_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 -0.12778(4) 0.81437(3) 0.52910(2) 0.03157(14) Uani 1 1 d . . . . .
F2 F 1.25752(10) 0.46964(10) 0.20866(5) 0.0472(3) Uani 1 1 d . . . . .
F1 F 0.43581(13) 0.08598(9) 0.34996(7) 0.0621(3) Uani 1 1 d . . . . .
C13 C 0.68236(15) 0.62450(12) 0.34842(7) 0.0314(3) Uani 1 1 d . . . . .
H13 H 0.743965 0.688202 0.337706 0.038 Uiso 1 1 calc R . . . .
C14 C 0.54559(15) 0.65878(12) 0.37775(7) 0.0296(3) Uani 1 1 d . . . . .
C15 C 0.48892(16) 0.77145(12) 0.36416(7) 0.0318(3) Uani 1 1 d . . . . .
H15 H 0.539945 0.823396 0.336703 0.038 Uiso 1 1 calc R . . . .
C9 C 0.51610(16) 0.38818(13) 0.30758(7) 0.0349(3) Uani 1 1 d . . . . .
H9 H 0.475107 0.451012 0.281844 0.042 Uiso 1 1 calc R . . . .
C18 C 0.34333(16) 0.62391(13) 0.44665(7) 0.0335(3) Uani 1 1 d . . . . .
H18 H 0.294820 0.573435 0.475845 0.040 Uiso 1 1 calc R . . . .
C17 C 0.36060(16) 0.80914(12) 0.38966(7) 0.0315(3) Uani 1 1 d . . . . .
H17 H 0.324116 0.885680 0.379084 0.038 Uiso 1 1 calc R . . . .
C6 C 0.87586(15) 0.50107(12) 0.30496(7) 0.0305(3) Uani 1 1 d . . . . .
C16 C 0.47032(16) 0.58666(12) 0.42050(7) 0.0336(3) Uani 1 1 d . . . . .
H16 H 0.507509 0.510599 0.431681 0.040 Uiso 1 1 calc R . . . .
C7 C 0.73257(15) 0.51595(12) 0.33464(7) 0.0305(3) Uani 1 1 d . . . . .
C8 C 0.64860(15) 0.40459(12) 0.34188(7) 0.0306(3) Uani 1 1 d . . . . .
C1 C 1.13299(16) 0.47853(14) 0.24154(8) 0.0360(3) Uani 1 1 d . . . . .
C4 C 0.89284(17) 0.41367(13) 0.25693(7) 0.0356(3) Uani 1 1 d . . . . .
H4 H 0.815078 0.361155 0.246225 0.043 Uiso 1 1 calc R . . . .
C12 C 0.44314(18) 0.28111(14) 0.31051(8) 0.0399(3) Uani 1 1 d . . . . .
H12 H 0.352704 0.269788 0.287184 0.048 Uiso 1 1 calc R . . . .
C19 C 0.28454(15) 0.73509(12) 0.43088(7) 0.0292(3) Uani 1 1 d . . . . .
C20 C 0.15002(16) 0.76928(12) 0.45792(7) 0.0314(3) Uani 1 1 d . . . . .
C21 C 0.03741(16) 0.79211(13) 0.48273(7) 0.0335(3) Uani 1 1 d . . . . .
C5 C 0.99409(16) 0.57344(13) 0.32190(7) 0.0354(3) Uani 1 1 d . . . . .
H5 H 0.985922 0.630892 0.355702 0.042 Uiso 1 1 calc R . . . .
C3 C 1.12383(16) 0.56295(14) 0.29016(8) 0.0385(3) Uani 1 1 d . . . . .
H3 H 1.203856 0.612658 0.301719 0.046 Uiso 1 1 calc R . . . .
C2 C 1.02128(17) 0.40255(14) 0.22475(8) 0.0378(3) Uani 1 1 d . . . . .
H2 H 1.031769 0.343745 0.191864 0.045 Uiso 1 1 calc R . . . .
C10 C 0.70664(17) 0.31166(13) 0.37968(8) 0.0375(3) Uani 1 1 d . . . . .
H10 H 0.796964 0.321782 0.403300 0.045 Uiso 1 1 calc R . . . .
C22 C -0.25090(18) 0.91759(15) 0.48279(9) 0.0459(4) Uani 1 1 d . . . . .
H22A H -0.206671 0.996277 0.481985 0.069 Uiso 1 1 calc GR . . . .
H22B H -0.343283 0.922106 0.504443 0.069 Uiso 1 1 calc GR . . . .
H22C H -0.267781 0.888904 0.437474 0.069 Uiso 1 1 calc GR . . . .
C11 C 0.6345(2) 0.20486(15) 0.38329(9) 0.0450(4) Uani 1 1 d . . . . .
H11 H 0.673545 0.141924 0.409546 0.054 Uiso 1 1 calc R . . . .
C00Q C 0.5054(2) 0.19214(13) 0.34807(9) 0.0426(4) Uani 1 1 d . . . . .
C23 C -0.07046(19) 0.87732(19) 0.61079(9) 0.0500(4) Uani 1 1 d . . . . .
H23A H -0.008426 0.820424 0.635137 0.075 Uiso 1 1 calc GR . . . .
H23B H -0.156137 0.894020 0.635904 0.075 Uiso 1 1 calc GR . . . .
H23C H -0.016579 0.950734 0.604445 0.075 Uiso 1 1 calc GR . . . .
C24 C -0.2110(2) 0.66602(15) 0.53762(9) 0.0479(4) Uani 1 1 d . . . . .
H24A H -0.223798 0.629162 0.493999 0.072 Uiso 1 1 calc GR . . . .
H24B H -0.305401 0.674180 0.557192 0.072 Uiso 1 1 calc GR . . . .
H24C H -0.147719 0.616441 0.566179 0.072 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 C21 1.8481(16) . ?
Si1 C22 1.8549(17) . ?
Si1 C23 1.8572(17) . ?
Si1 C24 1.8575(17) . ?
F2 C1 1.3612(17) . ?
F1 C00Q 1.3638(18) . ?
C13 C14 1.474(2) . ?
C13 C7 1.347(2) . ?
C14 C15 1.4004(19) . ?
C14 C16 1.399(2) . ?
C15 C17 1.384(2) . ?
C9 C8 1.393(2) . ?
C9 C12 1.389(2) . ?
C18 C16 1.377(2) . ?
C18 C19 1.401(2) . ?
C17 C19 1.396(2) . ?
C6 C7 1.4903(19) . ?
C6 C4 1.402(2) . ?
C6 C5 1.396(2) . ?
C7 C8 1.4905(19) . ?
C8 C10 1.393(2) . ?
C1 C3 1.378(2) . ?
C1 C2 1.374(2) . ?
C4 C2 1.387(2) . ?
C12 C00Q 1.372(2) . ?
C19 C20 1.436(2) . ?
C20 C21 1.206(2) . ?
C5 C3 1.393(2) . ?
C10 C11 1.384(2) . ?
C11 C00Q 1.370(3) . ?

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
C21 Si1 C22 109.30(8) . . ?
C21 Si1 C23 107.32(7) . . ?
C21 Si1 C24 106.27(8) . . ?
C22 Si1 C23 110.67(9) . . ?
C22 Si1 C24 111.62(8) . . ?
C23 Si1 C24 111.44(9) . . ?
C7 C13 C14 129.35(13) . . ?
C15 C14 C13 118.69(12) . . ?
C16 C14 C13 123.88(13) . . ?
C16 C14 C15 117.39(13) . . ?
C17 C15 C14 121.77(13) . . ?
C12 C9 C8 120.83(14) . . ?
C16 C18 C19 121.03(13) . . ?
C15 C17 C19 120.24(13) . . ?
C4 C6 C7 119.40(13) . . ?
C5 C6 C7 122.37(13) . . ?
C5 C6 C4 118.21(14) . . ?
C18 C16 C14 121.20(13) . . ?
C13 C7 C6 120.56(13) . . ?
C13 C7 C8 124.32(13) . . ?
C6 C7 C8 114.93(11) . . ?
C9 C8 C7 120.90(12) . . ?
C9 C8 C10 118.78(14) . . ?
C10 C8 C7 120.17(13) . . ?
F2 C1 C3 118.91(14) . . ?
F2 C1 C2 118.41(14) . . ?
C2 C1 C3 122.68(14) . . ?
C2 C4 C6 121.13(14) . . ?
C00Q C12 C9 118.10(15) . . ?
C18 C19 C20 119.23(13) . . ?
C17 C19 C18 118.30(13) . . ?
C17 C19 C20 122.46(13) . . ?
C21 C20 C19 176.25(15) . . ?
C20 C21 Si1 172.85(13) . . ?
C3 C5 C6 121.20(14) . . ?
C1 C3 C5 118.21(14) . . ?
C1 C2 C4 118.48(14) . . ?
C11 C10 C8 120.89(15) . . ?
C00Q C11 C10 118.35(15) . . ?
F1 C00Q C12 118.34(16) . . ?
F1 C00Q C11 118.62(15) . . ?
C11 C00Q C12 123.04(15) . . ?

_olex2_submission_original_sample_id C25H22F2Si
_olex2_submission_special_instructions 'No special instructions were received'
