# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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data_mo_210107_zdj_1_092_0m
_database_code_depnum_ccdc_archive 'CCDC 2082268'
loop_
_audit_author_name
_audit_author_address
'Jiyong Liu'
;Zhejiang university
China
;
_audit_update_record             
;
2021-05-07 deposited with the CCDC.	2024-05-19 downloaded from the CCDC.
;
_audit_creation_date             2021-01-07
_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         'C21 H21 F3 O4'
_chemical_formula_sum            'C21 H21 F3 O4'
_chemical_formula_weight         394.38
_chemical_absolute_configuration unk
_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'
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                   12.352(3)
_cell_length_b                   5.4853(16)
_cell_length_c                   15.561(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.325(11)
_cell_angle_gamma                90
_cell_volume                     982.1(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9669
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.64
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1666 before and 0.0801 after correction.
The Ratio of minimum to maximum transmission is 0.9027.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15972
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.105
_diffrn_reflns_theta_min         2.630
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                4033
_reflns_number_total             4302
_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 V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_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         0.636
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 1638 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(3)
_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     256
_refine_ls_number_reflns         4302
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0520
_refine_ls_restrained_S_all      1.061
_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)+(0.0773P)²+0.4214P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1426
_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:
 C8(H8A,H8B), C11(H11A,H11B), C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_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 0.2110(4) 0.1051(11) 0.3714(2) 0.1287(19) Uani 1 1 d . . . . .
F2 F 0.2181(3) 0.4662(8) 0.4057(3) 0.0975(13) Uani 1 1 d . . . . .
F3 F 0.1308(2) 0.2131(13) 0.4608(2) 0.130(2) Uani 1 1 d . . . . .
O1 O 0.5088(2) -0.2420(5) 0.84089(17) 0.0378(5) Uani 1 1 d . . . . .
O2 O 0.56842(19) 0.0077(5) 0.96281(15) 0.0341(5) Uani 1 1 d . . . . .
O3 O 1.0204(3) 1.1718(4) 0.85075(19) 0.0414(6) Uani 1 1 d . . . . .
O4 O 1.1053(2) 0.8951(4) 0.78829(17) 0.0327(5) Uani 1 1 d . . . . .
C1 C 0.4977(3) -0.0445(6) 0.6018(2) 0.0340(7) Uani 1 1 d . . . . .
H1 H 0.541524 -0.188029 0.603581 0.041 Uiso 1 1 calc R . . . .
C2 C 0.3956(3) -0.0022(7) 0.5261(2) 0.0387(8) Uani 1 1 d . . . . .
H2 H 0.370112 -0.115587 0.476596 0.046 Uiso 1 1 calc R . . . .
C3 C 0.3328(3) 0.2048(7) 0.5241(2) 0.0402(8) Uani 1 1 d . . . . .
C4 C 0.3699(3) 0.3733(7) 0.5961(2) 0.0378(7) Uani 1 1 d . . . . .
H4 H 0.325965 0.516932 0.593829 0.045 Uiso 1 1 calc R . . . .
C5 C 0.4718(3) 0.3298(6) 0.6715(2) 0.0321(7) Uani 1 1 d . . . . .
H5 H 0.497277 0.443385 0.720946 0.039 Uiso 1 1 calc R . . . .
C6 C 0.5359(3) 0.1198(6) 0.6743(2) 0.0280(6) Uani 1 1 d . . . . .
C7 C 0.2208(4) 0.2541(11) 0.4443(3) 0.0593(12) Uani 1 1 d . . . . .
C8 C 0.6485(3) 0.0704(7) 0.7550(2) 0.0319(7) Uani 1 1 d . . . . .
H8A H 0.674405 -0.098007 0.750042 0.038 Uiso 1 1 calc R . . . .
H8B H 0.709260 0.183256 0.751401 0.038 Uiso 1 1 calc R . . . .
C9 C 0.6361(2) 0.1009(6) 0.8468(2) 0.0250(6) Uani 1 1 d . . . . .
C10 C 0.5643(2) -0.0668(6) 0.8783(2) 0.0274(6) Uani 1 1 d . . . . .
C11 C 0.6399(3) 0.2241(6) 0.9907(2) 0.0307(6) Uani 1 1 d . . . . .
H11A H 0.705686 0.196682 1.049531 0.037 Uiso 1 1 calc R . . . .
H11B H 0.593666 0.364588 0.998059 0.037 Uiso 1 1 calc R . . . .
C12 C 0.6825(2) 0.2665(6) 0.91276(19) 0.0246(6) Uani 1 1 d . . . . .
C13 C 0.7620(2) 0.4575(6) 0.9154(2) 0.0269(6) Uani 1 1 d . . . . .
C14 C 0.8305(3) 0.6157(6) 0.9194(2) 0.0269(6) Uani 1 1 d . . . . .
C15 C 0.9152(3) 0.8056(5) 0.9207(2) 0.0262(6) Uani 1 1 d . . . . .
H15A H 0.973282 0.821306 0.984038 0.031 Uiso 1 1 calc R . . . .
H15B H 0.874556 0.963835 0.903267 0.031 Uiso 1 1 calc R . . . .
C16 C 0.9774(3) 0.7474(6) 0.8547(2) 0.0309(6) Uani 1 1 d . . . . .
H16A H 1.036279 0.619386 0.882466 0.037 Uiso 1 1 calc R . . . .
H16B H 0.920336 0.681301 0.796686 0.037 Uiso 1 1 calc R . . . .
C17 C 1.0363(3) 0.9648(6) 0.8323(2) 0.0272(6) Uani 1 1 d . . . . .
C18 C 1.1645(3) 1.0718(6) 0.7474(2) 0.0327(7) Uani 1 1 d . . . . .
C19 C 1.2232(4) 0.9049(8) 0.7001(3) 0.0521(10) Uani 1 1 d . . . . .
H19A H 1.274577 0.791551 0.745322 0.078 Uiso 1 1 calc GR . . . .
H19B H 1.268926 1.002551 0.672787 0.078 Uiso 1 1 calc GR . . . .
H19C H 1.164039 0.812619 0.651434 0.078 Uiso 1 1 calc GR . . . .
C20 C 1.2536(4) 1.2183(8) 0.8249(3) 0.0484(9) Uani 1 1 d . . . . .
H20A H 1.213040 1.320332 0.855326 0.073 Uiso 1 1 calc GR . . . .
H20B H 1.298620 1.322091 0.798959 0.073 Uiso 1 1 calc GR . . . .
H20C H 1.306025 1.106115 0.870022 0.073 Uiso 1 1 calc GR . . . .
C21 C 1.0755(3) 1.2359(8) 0.6794(3) 0.0436(8) Uani 1 1 d . . . . .
H21A H 1.012074 1.136473 0.637869 0.065 Uiso 1 1 calc GR . . . .
H21B H 1.112473 1.326941 0.643229 0.065 Uiso 1 1 calc GR . . . .
H21C H 1.044483 1.350341 0.712943 0.065 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
F1 C7 1.367(7) . ?
F2 C7 1.304(6) . ?
F3 C7 1.250(5) . ?
O1 C10 1.201(4) . ?
O2 C10 1.360(4) . ?
O2 C11 1.448(4) . ?
O3 C17 1.204(4) . ?
O4 C17 1.329(4) . ?
O4 C18 1.489(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.396(5) . ?
C1 C6 1.386(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.370(6) . ?
C3 C4 1.396(5) . ?
C3 C7 1.510(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(5) . ?
C6 C8 1.522(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.500(4) . ?
C9 C10 1.480(4) . ?
C9 C12 1.334(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.506(4) . ?
C12 C13 1.426(4) . ?
C13 C14 1.198(4) . ?
C14 C15 1.471(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.523(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.502(4) . ?
C18 C19 1.515(5) . ?
C18 C20 1.531(5) . ?
C18 C21 1.514(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C10 O2 C11 109.9(2) . . ?
C17 O4 C18 122.7(2) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C6 C1 C2 120.9(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 C7 120.6(4) . . ?
C4 C3 C7 118.5(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.5(3) . . ?
C1 C6 C8 119.7(3) . . ?
C5 C6 C8 120.8(3) . . ?
F1 C7 C3 110.7(4) . . ?
F2 C7 F1 99.9(4) . . ?
F2 C7 C3 113.6(4) . . ?
F3 C7 F1 104.3(5) . . ?
F3 C7 F2 112.3(5) . . ?
F3 C7 C3 114.6(3) . . ?
C6 C8 H8A 109.0 . . ?
C6 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C6 112.8(2) . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C10 C9 C8 121.8(3) . . ?
C12 C9 C8 130.2(3) . . ?
C12 C9 C10 108.0(3) . . ?
O1 C10 O2 121.6(3) . . ?
O1 C10 C9 129.9(3) . . ?
O2 C10 C9 108.5(3) . . ?
O2 C11 H11A 111.0 . . ?
O2 C11 H11B 111.0 . . ?
O2 C11 C12 103.8(2) . . ?
H11A C11 H11B 109.0 . . ?
C12 C11 H11A 111.0 . . ?
C12 C11 H11B 111.0 . . ?
C9 C12 C11 109.7(3) . . ?
C9 C12 C13 128.4(3) . . ?
C13 C12 C11 121.9(3) . . ?
C14 C13 C12 178.5(3) . . ?
C13 C14 C15 177.5(3) . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C14 C15 C16 111.9(2) . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 C15 113.3(3) . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
O3 C17 O4 125.7(3) . . ?
O3 C17 C16 124.0(3) . . ?
O4 C17 C16 110.2(3) . . ?
O4 C18 C19 102.2(3) . . ?
O4 C18 C20 109.2(3) . . ?
O4 C18 C21 110.0(3) . . ?
C19 C18 C20 111.5(3) . . ?
C21 C18 C19 111.9(3) . . ?
C21 C18 C20 111.7(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
