# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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. 
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#######################################################################

data_mjl18402_0m
_database_code_depnum_ccdc_archive 'CCDC 1913895'
loop_
_audit_author_name
_audit_author_address
'dong wei'
;Shanghai Institute of Organic Chemistry, CAS
China
;
_audit_update_record             
;
2019-05-04 deposited with the CCDC.	2023-06-13 downloaded from the CCDC.
;
_audit_creation_date             2018-08-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H21 F3'
_chemical_formula_sum            'C30 H21 F3'
_chemical_formula_weight         438.47
_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 0.0148 0.0070 '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 0.0599 0.0411 '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                   9.26090(10)
_cell_length_b                   10.8518(2)
_cell_length_c                   11.3998(2)
_cell_angle_alpha                73.3310(10)
_cell_angle_beta                 86.7220(10)
_cell_angle_gamma                83.7240(10)
_cell_volume                     1090.53(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7553
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.92
_cell_measurement_theta_min      5.32
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    0.495
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0709 before and 0.0435 after correction. The Ratio of minimum to maximum transmission is 0.8440. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11640
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.916
_diffrn_reflns_theta_min         3.717
_diffrn_ambient_temperature      170.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3592
_reflns_number_total             4096
_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         0.407
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4096
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.031
_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)+(0.0543P)²+0.5468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1194
_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 Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C26(H26), C27(H27),
  C28(H28), C29(H29), C30(H30)
2.b X=CH2 refined with riding coordinates:
 C24(H24A,H24B)
;
_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
F1 F 0.90757(14) 0.11651(12) 0.01022(16) 0.0792(5) Uani 1 1 d . . . . .
F2 F 0.83556(17) -0.03045(12) 0.16144(13) 0.0780(5) Uani 1 1 d . . . . .
F3 F 0.72204(14) 0.02177(13) -0.00210(13) 0.0624(4) Uani 1 1 d . . . . .
C1 C 0.29989(15) 0.25769(13) 0.21332(13) 0.0214(3) Uani 1 1 d . . . . .
C2 C 0.28076(15) 0.38415(13) 0.25095(12) 0.0209(3) Uani 1 1 d . . . . .
C3 C 0.40884(15) 0.43712(13) 0.23944(12) 0.0215(3) Uani 1 1 d . . . . .
C4 C 0.52329(15) 0.35446(13) 0.19665(13) 0.0220(3) Uani 1 1 d . . . . .
C5 C 0.67073(16) 0.36800(15) 0.17328(15) 0.0279(3) Uani 1 1 d . . . . .
H5 H 0.712105 0.439668 0.185261 0.033 Uiso 1 1 calc R . . . .
C6 C 0.75613(17) 0.27462(15) 0.13208(15) 0.0302(4) Uani 1 1 d . . . . .
H6 H 0.856976 0.282309 0.115551 0.036 Uiso 1 1 calc R . . . .
C7 C 0.69488(16) 0.17004(14) 0.11493(14) 0.0266(3) Uani 1 1 d . . . . .
C8 C 0.54717(16) 0.15422(14) 0.14116(13) 0.0238(3) Uani 1 1 d . . . . .
H8 H 0.506234 0.081392 0.131272 0.029 Uiso 1 1 calc R . . . .
C9 C 0.46313(15) 0.24750(13) 0.18172(12) 0.0212(3) Uani 1 1 d . . . . .
C10 C 0.78997(18) 0.07153(15) 0.07058(16) 0.0344(4) Uani 1 1 d . . . . .
C11 C 0.43882(15) 0.55825(13) 0.26424(13) 0.0225(3) Uani 1 1 d . . . . .
C12 C 0.40405(16) 0.57977(15) 0.37760(14) 0.0266(3) Uani 1 1 d . . . . .
H12 H 0.360588 0.515683 0.440554 0.032 Uiso 1 1 calc R . . . .
C13 C 0.43231(18) 0.69377(16) 0.39930(15) 0.0327(4) Uani 1 1 d . . . . .
H13 H 0.409028 0.707006 0.477304 0.039 Uiso 1 1 calc R . . . .
C14 C 0.4940(2) 0.78836(16) 0.30853(17) 0.0374(4) Uani 1 1 d . . . . .
H14 H 0.511583 0.867188 0.323278 0.045 Uiso 1 1 calc R . . . .
C15 C 0.5303(2) 0.76754(16) 0.19570(16) 0.0379(4) Uani 1 1 d . . . . .
H15 H 0.573563 0.832081 0.133117 0.045 Uiso 1 1 calc R . . . .
C16 C 0.50369(18) 0.65321(15) 0.17364(14) 0.0300(3) Uani 1 1 d . . . . .
H16 H 0.529827 0.639365 0.096281 0.036 Uiso 1 1 calc R . . . .
C17 C 0.13894(15) 0.44264(14) 0.28642(13) 0.0232(3) Uani 1 1 d . . . . .
C18 C 0.03778(17) 0.36971(16) 0.36310(15) 0.0313(4) Uani 1 1 d . . . . .
H18 H 0.058441 0.278642 0.393163 0.038 Uiso 1 1 calc R . . . .
C19 C -0.09284(18) 0.42832(17) 0.39619(17) 0.0383(4) Uani 1 1 d . . . . .
H19 H -0.159921 0.377026 0.449404 0.046 Uiso 1 1 calc R . . . .
C20 C -0.12642(18) 0.56037(17) 0.35262(16) 0.0356(4) Uani 1 1 d . . . . .
H20 H -0.216191 0.599927 0.375195 0.043 Uiso 1 1 calc R . . . .
C21 C -0.02758(18) 0.63431(16) 0.27566(15) 0.0333(4) Uani 1 1 d . . . . .
H21 H -0.049553 0.725204 0.245237 0.040 Uiso 1 1 calc R . . . .
C22 C 0.10345(17) 0.57632(15) 0.24272(14) 0.0286(3) Uani 1 1 d . . . . .
H22 H 0.170163 0.628181 0.189644 0.034 Uiso 1 1 calc R . . . .
C23 C 0.22157(16) 0.27010(15) 0.09637(13) 0.0258(3) Uani 1 1 d . . . . .
H23 H 0.224772 0.194324 0.070029 0.031 Uiso 1 1 calc R . . . .
C24 C 0.14990(18) 0.37471(17) 0.02789(15) 0.0334(4) Uani 1 1 d . . . . .
H24A H 0.143373 0.453106 0.050137 0.040 Uiso 1 1 calc R . . . .
H24B H 0.104570 0.371986 -0.043889 0.040 Uiso 1 1 calc R . . . .
C25 C 0.26322(15) 0.13867(14) 0.31771(13) 0.0232(3) Uani 1 1 d . . . . .
C26 C 0.32784(19) 0.11448(16) 0.42985(15) 0.0355(4) Uani 1 1 d . . . . .
H26 H 0.394439 0.170832 0.440469 0.043 Uiso 1 1 calc R . . . .
C27 C 0.2965(2) 0.00898(18) 0.52681(16) 0.0408(4) Uani 1 1 d . . . . .
H27 H 0.341143 -0.005755 0.603247 0.049 Uiso 1 1 calc R . . . .
C28 C 0.20146(19) -0.07423(16) 0.51308(16) 0.0377(4) Uani 1 1 d . . . . .
H28 H 0.179798 -0.146159 0.579659 0.045 Uiso 1 1 calc R . . . .
C29 C 0.1381(2) -0.05232(17) 0.40206(17) 0.0408(4) Uani 1 1 d . . . . .
H29 H 0.073057 -0.110073 0.391675 0.049 Uiso 1 1 calc R . . . .
C30 C 0.16812(18) 0.05359(16) 0.30464(15) 0.0323(4) Uani 1 1 d . . . . .
H30 H 0.123079 0.067766 0.228463 0.039 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
F1 C10 1.3175(19) . ?
F2 C10 1.329(2) . ?
F3 C10 1.328(2) . ?
C1 C2 1.5409(19) . ?
C1 C9 1.5334(19) . ?
C1 C23 1.519(2) . ?
C1 C25 1.5386(19) . ?
C2 C3 1.357(2) . ?
C2 C17 1.482(2) . ?
C3 C4 1.466(2) . ?
C3 C11 1.479(2) . ?
C4 C5 1.392(2) . ?
C4 C9 1.397(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.389(2) . ?
C7 C8 1.402(2) . ?
C7 C10 1.492(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.378(2) . ?
C11 C12 1.392(2) . ?
C11 C16 1.394(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(2) . ?
C17 C22 1.400(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.388(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.382(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.388(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.313(2) . ?
C24 H24A 0.9500 . ?
C24 H24B 0.9500 . ?
C25 C26 1.386(2) . ?
C25 C30 1.386(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.388(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.373(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.373(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.391(2) . ?
C30 H30 0.9500 . ?

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
C9 C1 C2 101.22(11) . . ?
C9 C1 C25 109.90(11) . . ?
C23 C1 C2 112.15(12) . . ?
C23 C1 C9 106.77(11) . . ?
C23 C1 C25 112.65(12) . . ?
C25 C1 C2 113.32(11) . . ?
C3 C2 C1 110.68(12) . . ?
C3 C2 C17 125.44(13) . . ?
C17 C2 C1 123.76(12) . . ?
C2 C3 C4 109.61(12) . . ?
C2 C3 C11 128.51(13) . . ?
C4 C3 C11 121.87(12) . . ?
C5 C4 C3 130.39(13) . . ?
C5 C4 C9 120.66(13) . . ?
C9 C4 C3 108.95(12) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.65(14) . . ?
C6 C5 H5 120.7 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.33(14) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C8 121.27(14) . . ?
C6 C7 C10 118.87(14) . . ?
C8 C7 C10 119.84(14) . . ?
C7 C8 H8 121.0 . . ?
C9 C8 C7 118.00(13) . . ?
C9 C8 H8 121.0 . . ?
C4 C9 C1 109.52(12) . . ?
C8 C9 C1 129.40(13) . . ?
C8 C9 C4 121.06(13) . . ?
F1 C10 F2 106.29(16) . . ?
F1 C10 F3 107.04(15) . . ?
F1 C10 C7 113.33(13) . . ?
F2 C10 C7 112.47(14) . . ?
F3 C10 F2 104.10(15) . . ?
F3 C10 C7 112.93(14) . . ?
C12 C11 C3 121.17(13) . . ?
C12 C11 C16 118.71(13) . . ?
C16 C11 C3 120.12(13) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.50(14) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.50(15) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.50(15) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.36(15) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.41(15) . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C2 122.54(13) . . ?
C18 C17 C22 117.77(14) . . ?
C22 C17 C2 119.68(13) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.88(15) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.77(16) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.15(15) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.33(15) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 H22 119.5 . . ?
C21 C22 C17 121.09(15) . . ?
C21 C22 H22 119.5 . . ?
C1 C23 H23 116.6 . . ?
C24 C23 C1 126.76(14) . . ?
C24 C23 H23 116.6 . . ?
C23 C24 H24A 120.0 . . ?
C23 C24 H24B 120.0 . . ?
H24A C24 H24B 120.0 . . ?
C26 C25 C1 119.02(13) . . ?
C30 C25 C1 122.81(13) . . ?
C30 C25 C26 118.16(14) . . ?
C25 C26 H26 119.6 . . ?
C25 C26 C27 120.86(16) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.49(17) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 120.4 . . ?
C29 C28 C27 119.26(15) . . ?
C29 C28 H28 120.4 . . ?
C28 C29 H29 119.7 . . ?
C28 C29 C30 120.64(16) . . ?
C30 C29 H29 119.7 . . ?
C25 C30 C29 120.58(16) . . ?
C25 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
