# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20201109_ny_1
_database_code_depnum_ccdc_archive 'CCDC 2100022'
loop_
_audit_author_name
_audit_author_address
'Yong Nie'
;University of Jinan
China
;
_audit_update_record             
;
2021-08-02 deposited with the CCDC.	2022-05-03 downloaded from the CCDC.
;
_audit_creation_date             2020-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H19 F O'
_chemical_formula_sum            'C27 H19 F O'
_chemical_formula_weight         378.42
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N'
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'
O O 0.0106 0.0060 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.2779(7)
_cell_length_b                   9.1125(5)
_cell_length_c                   11.3260(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.418(7)
_cell_angle_gamma                90
_cell_volume                     1017.51(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1553
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.9810
_cell_measurement_theta_min      3.7290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65592
_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    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6090
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.255
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0355
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.00  83.00   1.00   15.00    --   16.17  57.00  90.00   84
  2  ω    -13.00  88.00   1.00   15.00    --   16.17  19.00  30.00  101
  3  ω    -25.00  22.00   1.00   15.00    --  -16.64 -99.00-180.00   47
  4  ω    -51.00  43.00   1.00   15.00    --   16.17 -77.00 -30.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0322163000
_diffrn_orient_matrix_UB_12      -0.0013237000
_diffrn_orient_matrix_UB_13      -0.0477364000
_diffrn_orient_matrix_UB_21      -0.0637727000
_diffrn_orient_matrix_UB_22      -0.0109717000
_diffrn_orient_matrix_UB_23      -0.0439767000
_diffrn_orient_matrix_UB_31      -0.0084878000
_diffrn_orient_matrix_UB_32      0.0770373000
_diffrn_orient_matrix_UB_33      -0.0070670000
_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         0.763
_reflns_Friedel_fraction_full    0.872
_reflns_Friedel_fraction_max     0.871
_reflns_number_gt                2290
_reflns_number_total             3498
_reflns_odcompleteness_completeness 99.64
_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 1.171.39.46e (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 784 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3498
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      0.970
_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)+(0.0602P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1258
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
  C25(H25), C26(H26), C27(H27)
;
_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
F2 F -0.5822(4) -0.5980(4) -0.8180(2) 0.1191(14) Uani 1 1 d . . . . .
O1 O -0.8192(5) -0.3919(5) -0.6493(4) 0.1050(13) Uani 1 1 d . . . . .
C1 C -0.7478(7) -0.4597(7) -0.6968(5) 0.0862(17) Uani 1 1 d . . . . .
H1 H -0.7808 -0.4788 -0.7806 0.103 Uiso 1 1 calc R . . . .
C2 C -0.6144(5) -0.5138(5) -0.6335(4) 0.0625(12) Uani 1 1 d . . . . .
C3 C -0.5329(7) -0.5812(6) -0.6939(4) 0.0736(15) Uani 1 1 d . . . . .
C4 C -0.4086(7) -0.6349(6) -0.6377(5) 0.0767(15) Uani 1 1 d . . . . .
H4 H -0.3563 -0.6794 -0.6826 0.092 Uiso 1 1 calc R . . . .
C5 C -0.3618(5) -0.6220(5) -0.5124(4) 0.0622(13) Uani 1 1 d . . . . .
H5 H -0.2769 -0.6601 -0.4722 0.075 Uiso 1 1 calc R . . . .
C6 C -0.4363(4) -0.5541(4) -0.4430(3) 0.0490(10) Uani 1 1 d . . . . .
C7 C -0.5630(5) -0.5022(5) -0.5047(4) 0.0576(11) Uani 1 1 d . . . . .
H7 H -0.6160 -0.4584 -0.4602 0.069 Uiso 1 1 calc R . . . .
C8 C -0.3861(4) -0.5431(4) -0.3075(3) 0.0463(10) Uani 1 1 d . . . . .
C9 C -0.4868(4) -0.5753(5) -0.2390(3) 0.0490(10) Uani 1 1 d . . . . .
C10 C -0.5668(5) -0.7005(5) -0.2637(4) 0.0610(12) Uani 1 1 d . . . . .
H10 H -0.5595 -0.7644 -0.3256 0.073 Uiso 1 1 calc R . . . .
C11 C -0.6571(5) -0.7310(6) -0.1970(5) 0.0795(15) Uani 1 1 d . . . . .
H11 H -0.7086 -0.8164 -0.2129 0.095 Uiso 1 1 calc R . . . .
C12 C -0.6713(6) -0.6363(8) -0.1077(5) 0.0848(16) Uani 1 1 d . . . . .
H12 H -0.7317 -0.6578 -0.0626 0.102 Uiso 1 1 calc R . . . .
C13 C -0.5969(5) -0.5105(6) -0.0851(4) 0.0698(13) Uani 1 1 d . . . . .
H13 H -0.6083 -0.4452 -0.0257 0.084 Uiso 1 1 calc R . . . .
C14 C -0.5050(4) -0.4794(5) -0.1496(4) 0.0571(11) Uani 1 1 d . . . . .
H14 H -0.4546 -0.3933 -0.1331 0.069 Uiso 1 1 calc R . . . .
C15 C -0.2560(4) -0.5077(4) -0.2481(3) 0.0475(10) Uani 1 1 d . . . . .
C16 C -0.1979(4) -0.5228(4) -0.1127(4) 0.0477(10) Uani 1 1 d . . . . .
C17 C -0.2157(5) -0.6506(5) -0.0512(4) 0.0617(12) Uani 1 1 d . . . . .
H17 H -0.2644 -0.7281 -0.0961 0.074 Uiso 1 1 calc R . . . .
C18 C -0.1634(5) -0.6647(6) 0.0731(4) 0.0725(14) Uani 1 1 d . . . . .
H18 H -0.1778 -0.7507 0.1118 0.087 Uiso 1 1 calc R . . . .
C19 C -0.0900(5) -0.5534(7) 0.1414(4) 0.0774(15) Uani 1 1 d . . . . .
H19 H -0.0556 -0.5626 0.2263 0.093 Uiso 1 1 calc R . . . .
C20 C -0.0675(5) -0.4270(6) 0.0827(4) 0.0720(14) Uani 1 1 d . . . . .
H20 H -0.0160 -0.3513 0.1280 0.086 Uiso 1 1 calc R . . . .
C21 C -0.1214(5) -0.4126(5) -0.0438(4) 0.0584(11) Uani 1 1 d . . . . .
H21 H -0.1055 -0.3272 -0.0824 0.070 Uiso 1 1 calc R . . . .
C22 C -0.1615(4) -0.4469(4) -0.3139(4) 0.0495(10) Uani 1 1 d . . . . .
C23 C -0.0292(4) -0.4976(5) -0.2916(4) 0.0606(12) Uani 1 1 d . . . . .
H23 H 0.0020 -0.5715 -0.2339 0.073 Uiso 1 1 calc R . . . .
C24 C 0.0562(5) -0.4395(7) -0.3541(5) 0.0763(15) Uani 1 1 d . . . . .
H24 H 0.1433 -0.4773 -0.3409 0.092 Uiso 1 1 calc R . . . .
C25 C 0.0131(6) -0.3261(7) -0.4357(5) 0.0829(16) Uani 1 1 d . . . . .
H25 H 0.0714 -0.2857 -0.4766 0.100 Uiso 1 1 calc R . . . .
C26 C -0.1141(7) -0.2737(6) -0.4564(5) 0.0812(16) Uani 1 1 d . . . . .
H26 H -0.1432 -0.1975 -0.5122 0.097 Uiso 1 1 calc R . . . .
C27 C -0.2015(5) -0.3314(5) -0.3961(4) 0.0611(12) Uani 1 1 d . . . . .
H27 H -0.2883 -0.2925 -0.4106 0.073 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
F2 C3 1.361(5) . ?
O1 C1 1.196(7) . ?
C1 H1 0.9300 . ?
C1 C2 1.443(7) . ?
C2 C3 1.368(7) . ?
C2 C7 1.409(6) . ?
C3 C4 1.348(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.369(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(6) . ?
C6 C7 1.376(6) . ?
C6 C8 1.478(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.487(5) . ?
C8 C15 1.355(5) . ?
C9 C10 1.388(6) . ?
C9 C14 1.390(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.380(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.368(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.361(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.486(5) . ?
C15 C22 1.489(6) . ?
C16 C17 1.395(6) . ?
C16 C21 1.374(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.364(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.366(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.388(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.390(6) . ?
C22 C27 1.388(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.380(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.374(8) . ?
C25 H25 0.9300 . ?
C25 C26 1.349(7) . ?
C26 H26 0.9300 . ?
C26 C27 1.377(7) . ?
C27 H27 0.9300 . ?

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
O1 C1 H1 117.6 . . ?
O1 C1 C2 124.8(5) . . ?
C2 C1 H1 117.6 . . ?
C3 C2 C1 122.4(5) . . ?
C3 C2 C7 116.6(5) . . ?
C7 C2 C1 121.0(5) . . ?
F2 C3 C2 117.7(5) . . ?
C4 C3 F2 118.3(5) . . ?
C4 C3 C2 124.0(4) . . ?
C3 C4 H4 121.1 . . ?
C3 C4 C5 117.8(5) . . ?
C5 C4 H4 121.1 . . ?
C4 C5 H5 118.8 . . ?
C4 C5 C6 122.5(5) . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C8 122.1(4) . . ?
C7 C6 C5 117.4(4) . . ?
C7 C6 C8 120.4(4) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 C2 121.6(4) . . ?
C6 C7 H7 119.2 . . ?
C6 C8 C9 116.0(3) . . ?
C15 C8 C6 122.5(3) . . ?
C15 C8 C9 121.5(3) . . ?
C10 C9 C8 121.2(4) . . ?
C10 C9 C14 118.0(4) . . ?
C14 C9 C8 120.9(4) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.5(5) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(5) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.9(5) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(5) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.7(5) . . ?
C13 C14 H14 119.6 . . ?
C8 C15 C16 122.8(3) . . ?
C8 C15 C22 122.2(4) . . ?
C16 C15 C22 115.0(4) . . ?
C17 C16 C15 121.4(4) . . ?
C21 C16 C15 121.1(4) . . ?
C21 C16 C17 117.4(4) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.7(5) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.5(5) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.4 . . ?
C18 C19 C20 119.2(4) . . ?
C20 C19 H19 120.4 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.2(5) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 121.0(4) . . ?
C16 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C23 C22 C15 121.9(4) . . ?
C27 C22 C15 120.4(4) . . ?
C27 C22 C23 117.6(4) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.7(4) . . ?
C24 C23 H23 119.6 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.2(5) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.7(4) . . ?
C26 C25 H25 120.2 . . ?
C25 C26 H26 119.5 . . ?
C25 C26 C27 121.0(5) . . ?
C27 C26 H26 119.5 . . ?
C22 C27 H27 119.6 . . ?
C26 C27 C22 120.7(5) . . ?
C26 C27 H27 119.6 . . ?


_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.408
_oxdiff_exptl_absorpt_empirical_full_min 0.530
