# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_mo_20210121a_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2354856'
loop_
_audit_author_name
_audit_author_address
'Xinwei He'
;Anhui Normal University
China
;
_audit_update_record             
;
2024-05-13 deposited with the CCDC.	2024-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H11 F O3'
_chemical_formula_weight         294.27

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.9643(8)
_cell_length_b                   17.995(2)
_cell_length_c                   11.2480(13)
_cell_angle_alpha                90
_cell_angle_beta                 104.494(4)
_cell_angle_gamma                90
_cell_volume                     1364.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9377
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26551
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.937
_diffrn_reflns_theta_max         27.523
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3123
_reflns_number_gt                2243
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1500P)²+0.2669P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3123
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.2349
_refine_ls_wR_factor_gt          0.2102
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.2627(4) 0.92767(14) 0.5816(2) 0.0526(7) Uani 1 1 d . . . . .
C2 C 0.1209(4) 0.89294(15) 0.6265(2) 0.0536(7) Uani 1 1 d . . . . .
H2 H 0.028187 0.920276 0.655006 0.064 Uiso 1 1 calc R U . . .
C3 C 0.1190(4) 0.81630(13) 0.6285(2) 0.0432(6) Uani 1 1 d . . . . .
H3 H 0.023301 0.791755 0.658405 0.052 Uiso 1 1 calc R U . . .
C4 C 0.2578(3) 0.77504(12) 0.58648(18) 0.0345(5) Uani 1 1 d . . . . .
C5 C 0.3999(4) 0.81318(13) 0.5429(2) 0.0442(6) Uani 1 1 d . . . . .
H5 H 0.494484 0.786510 0.515174 0.053 Uiso 1 1 calc R U . . .
C6 C 0.4033(5) 0.88974(14) 0.5401(3) 0.0540(7) Uani 1 1 d . . . . .
H6 H 0.498707 0.914927 0.510860 0.065 Uiso 1 1 calc R U . . .
C7 C 0.2665(5) 0.66949(16) 0.8203(2) 0.0572(7) Uani 1 1 d . . . . .
H7A H 0.306696 0.720345 0.835678 0.086 Uiso 1 1 calc R U . . .
H7B H 0.362225 0.637591 0.872392 0.086 Uiso 1 1 calc R U . . .
H7C H 0.139324 0.662363 0.837203 0.086 Uiso 1 1 calc R U . . .
C8 C 0.2531(3) 0.65119(12) 0.6899(2) 0.0374(5) Uani 1 1 d . . . . .
C9 C 0.2556(3) 0.69308(13) 0.58996(19) 0.0346(5) Uani 1 1 d . . . . .
C10 C 0.2553(3) 0.64050(12) 0.49314(19) 0.0326(5) Uani 1 1 d . . . . .
C11 C 0.2492(3) 0.57165(12) 0.5418(2) 0.0333(5) Uani 1 1 d . . . . .
C12 C 0.2468(3) 0.50366(12) 0.4769(2) 0.0358(5) Uani 1 1 d . . . . .
C13 C 0.2385(3) 0.43156(13) 0.5224(3) 0.0441(6) Uani 1 1 d . . . . .
H13 H 0.231995 0.424295 0.603169 0.053 Uiso 1 1 calc R U . . .
C14 C 0.2399(4) 0.37144(15) 0.4466(3) 0.0538(7) Uani 1 1 d . . . . .
H14 H 0.233208 0.323611 0.476600 0.065 Uiso 1 1 calc R U . . .
C15 C 0.2512(4) 0.38122(15) 0.3267(3) 0.0577(8) Uani 1 1 d . . . . .
H15 H 0.253106 0.340041 0.277057 0.069 Uiso 1 1 calc R U . . .
C16 C 0.2595(4) 0.45189(16) 0.2802(3) 0.0524(7) Uani 1 1 d . . . . .
H16 H 0.267082 0.458396 0.199483 0.063 Uiso 1 1 calc R U . . .
C17 C 0.2566(3) 0.51299(13) 0.3547(2) 0.0404(6) Uani 1 1 d . . . . .
C18 C 0.2660(4) 0.64859(13) 0.3668(2) 0.0401(6) Uani 1 1 d . . . . .
F1 F 0.2632(3) 1.00329(9) 0.5759(2) 0.0888(7) Uani 1 1 d . . . . .
O1 O 0.2473(2) 0.57604(8) 0.66182(14) 0.0378(4) Uani 1 1 d . . . . .
O2 O 0.2781(3) 0.70471(11) 0.31165(16) 0.0609(6) Uani 1 1 d . . . . .
O3 O 0.2661(2) 0.58207(10) 0.30422(14) 0.0470(5) Uani 1 1 d . . . . .


_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
C1 F1 1.362(3) . ?
C1 C6 1.368(4) . ?
C1 C2 1.368(4) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(3) . ?
C4 C9 1.476(3) . ?
C5 C6 1.378(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.483(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.357(3) . ?
C8 O1 1.387(3) . ?
C9 C10 1.442(3) . ?
C10 C11 1.359(3) . ?
C10 C18 1.449(3) . ?
C11 O1 1.355(3) . ?
C11 C12 1.423(3) . ?
C12 C13 1.401(3) . ?
C12 C17 1.403(3) . ?
C13 C14 1.379(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.381(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9300 . ?
C17 O3 1.375(3) . ?
C18 O2 1.199(3) . ?
C18 O3 1.389(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
F1 C1 C6 118.2(2) . . ?
F1 C1 C2 119.0(2) . . ?
C6 C1 C2 122.9(2) . . ?
C1 C2 C3 118.2(2) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C2 C3 C4 121.2(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.2(2) . . ?
C5 C4 C9 121.0(2) . . ?
C3 C4 C9 120.8(2) . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 118.2(2) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 O1 111.01(19) . . ?
C9 C8 C7 133.2(2) . . ?
O1 C8 C7 115.6(2) . . ?
C8 C9 C10 105.3(2) . . ?
C8 C9 C4 125.4(2) . . ?
C10 C9 C4 129.32(19) . . ?
C11 C10 C9 106.73(18) . . ?
C11 C10 C18 120.07(19) . . ?
C9 C10 C18 133.16(19) . . ?
O1 C11 C10 110.92(18) . . ?
O1 C11 C12 124.00(19) . . ?
C10 C11 C12 125.1(2) . . ?
C13 C12 C17 119.0(2) . . ?
C13 C12 C11 127.3(2) . . ?
C17 C12 C11 113.7(2) . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 121.0(3) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.5(3) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
O3 C17 C16 117.2(2) . . ?
O3 C17 C12 122.1(2) . . ?
C16 C17 C12 120.6(2) . . ?
O2 C18 O3 117.0(2) . . ?
O2 C18 C10 128.3(2) . . ?
O3 C18 C10 114.67(19) . . ?
C11 O1 C8 106.06(16) . . ?
C17 O3 C18 124.29(18) . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.058



