# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_a_a
_audit_block_doi                 10.5517/ccdc.csd.cc28zg7z
_database_code_depnum_ccdc_archive 'CCDC 2114641'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1038/s41467-022-32467-x 2022
loop_
_audit_author_name
_audit_author_address
'Gangguo Zhu'
;Zhejiang Normal University
China
;
_audit_update_record             
;
2021-10-08 deposited with the CCDC.	2022-08-22 downloaded from the CCDC.
;
_audit_creation_date             2021-01-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 F3 O'
_chemical_formula_sum            'C14 H15 F3 O'
_chemical_formula_weight         256.26
_chemical_absolute_configuration ?
_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                   6.1123(5)
_cell_length_b                   7.4620(5)
_cell_length_c                   13.8843(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.134(3)
_cell_angle_gamma                90
_cell_volume                     629.64(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3359
_cell_measurement_temperature    250
_cell_measurement_theta_max      27.32
_cell_measurement_theta_min      2.95
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1129 before and 0.0408 after correction.
The Ratio of minimum to maximum transmission is 0.9403.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6263
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         2.951
_diffrn_ambient_temperature      250
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_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         0.837
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                2560
_reflns_number_total             2811
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    ?
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.097
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 
;
 Flack x determined using 1031 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2811
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.026
_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)+(0.0344P)²+0.0782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0805
_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 Ternary CH refined with riding coordinates:
 C005(H005), C006(H006)
2.b Secondary CH2 refined with riding coordinates:
 C00A(H00D,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00F), C00F(H00J), C00G(H00K), C00H(H00L), C00I(H00M)
2.d Idealised Me refined as rotating group:
 C009(H00A,H00B,H00C), C00E(H00G,H00H,H00I)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
F001 F 1.0696(2) 0.39766(19) 0.59227(10) 0.0548(4) Uani 1 1 d . . . . .
F002 F 0.8288(2) 0.2345(2) 0.51069(10) 0.0645(5) Uani 1 1 d . . . . .
F003 F 0.9237(3) 0.17810(19) 0.66067(12) 0.0663(5) Uani 1 1 d . . . . .
O004 O 0.6406(3) 0.5960(3) 0.47274(10) 0.0518(4) Uani 1 1 d . . . . .
C005 C 0.7529(3) 0.5083(3) 0.72875(14) 0.0325(4) Uani 1 1 d . . . . .
H005 H 0.9151 0.5172 0.7408 0.039 Uiso 1 1 calc R . . . .
C006 C 0.7022(3) 0.4330(3) 0.62515(14) 0.0334(4) Uani 1 1 d . . . . .
H006 H 0.5599 0.3684 0.6198 0.040 Uiso 1 1 calc R . . . .
C007 C 0.6817(3) 0.6007(3) 0.55949(13) 0.0365(4) Uani 1 1 d . . . . .
C008 C 0.6802(3) 0.3926(3) 0.80945(13) 0.0365(4) Uani 1 1 d . . . . .
C009 C 0.4160(4) 0.7158(3) 0.72703(17) 0.0485(5) Uani 1 1 d . . . . .
H00A H 0.3422 0.6376 0.6780 0.073 Uiso 1 1 calc GR . . . .
H00B H 0.3668 0.8382 0.7150 0.073 Uiso 1 1 calc GR . . . .
H00C H 0.3812 0.6783 0.7905 0.073 Uiso 1 1 calc GR . . . .
C00A C 0.7191(4) 0.7635(3) 0.62174(16) 0.0415(5) Uani 1 1 d . . . . .
H00D H 0.6226 0.8616 0.5967 0.050 Uiso 1 1 calc R . . . .
H00E H 0.8723 0.8034 0.6242 0.050 Uiso 1 1 calc R . . . .
C00B C 0.8788(4) 0.3105(3) 0.59672(15) 0.0419(5) Uani 1 1 d . . . . .
C00C C 0.4791(4) 0.3053(3) 0.80263(17) 0.0487(5) Uani 1 1 d . . . . .
H00F H 0.3822 0.3166 0.7457 0.058 Uiso 1 1 calc R . . . .
C00D C 0.6645(3) 0.7053(3) 0.72305(14) 0.0357(4) Uani 1 1 d . . . . .
C00E C 0.7823(4) 0.8209(3) 0.80291(16) 0.0494(5) Uani 1 1 d . . . . .
H00G H 0.7484 0.7775 0.8655 0.074 Uiso 1 1 calc GR . . . .
H00H H 0.7337 0.9441 0.7944 0.074 Uiso 1 1 calc GR . . . .
H00I H 0.9399 0.8145 0.7997 0.074 Uiso 1 1 calc GR . . . .
C00F C 0.8197(4) 0.3708(4) 0.89404(15) 0.0519(6) Uani 1 1 d . . . . .
H00J H 0.9581 0.4271 0.9005 0.062 Uiso 1 1 calc R . . . .
C00G C 0.4179(5) 0.2013(4) 0.8784(2) 0.0612(7) Uani 1 1 d . . . . .
H00K H 0.2802 0.1440 0.8726 0.073 Uiso 1 1 calc R . . . .
C00H C 0.5589(6) 0.1824(4) 0.96193(19) 0.0679(8) Uani 1 1 d . . . . .
H00L H 0.5182 0.1118 1.0132 0.081 Uiso 1 1 calc R . . . .
C00I C 0.7573(6) 0.2664(4) 0.96982(18) 0.0701(8) Uani 1 1 d . . . . .
H00M H 0.8535 0.2539 1.0269 0.084 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
F001 C00B 1.343(3) . ?
F002 C00B 1.328(2) . ?
F003 C00B 1.337(3) . ?
O004 C007 1.204(2) . ?
C005 H005 0.9900 . ?
C005 C006 1.545(3) . ?
C005 C008 1.518(3) . ?
C005 C00D 1.565(3) . ?
C006 H006 0.9900 . ?
C006 C007 1.545(3) . ?
C006 C00B 1.499(3) . ?
C007 C00A 1.495(3) . ?
C008 C00C 1.385(3) . ?
C008 C00F 1.385(3) . ?
C009 H00A 0.9700 . ?
C009 H00B 0.9700 . ?
C009 H00C 0.9700 . ?
C009 C00D 1.528(3) . ?
C00A H00D 0.9800 . ?
C00A H00E 0.9800 . ?
C00A C00D 1.542(3) . ?
C00C H00F 0.9400 . ?
C00C C00G 1.390(3) . ?
C00D C00E 1.524(3) . ?
C00E H00G 0.9700 . ?
C00E H00H 0.9700 . ?
C00E H00I 0.9700 . ?
C00F H00J 0.9400 . ?
C00F C00I 1.395(4) . ?
C00G H00K 0.9400 . ?
C00G C00H 1.376(4) . ?
C00H H00L 0.9400 . ?
C00H C00I 1.359(5) . ?
C00I H00M 0.9400 . ?

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
C006 C005 H005 106.2 . . ?
C006 C005 C00D 105.12(16) . . ?
C008 C005 H005 106.2 . . ?
C008 C005 C006 115.79(16) . . ?
C008 C005 C00D 116.43(16) . . ?
C00D C005 H005 106.2 . . ?
C005 C006 H006 109.5 . . ?
C005 C006 C007 104.50(16) . . ?
C007 C006 H006 109.5 . . ?
C00B C006 C005 112.87(17) . . ?
C00B C006 H006 109.5 . . ?
C00B C006 C007 110.71(16) . . ?
O004 C007 C006 124.2(2) . . ?
O004 C007 C00A 127.2(2) . . ?
C00A C007 C006 108.63(15) . . ?
C00C C008 C005 122.98(18) . . ?
C00F C008 C005 119.4(2) . . ?
C00F C008 C00C 117.6(2) . . ?
H00A C009 H00B 109.5 . . ?
H00A C009 H00C 109.5 . . ?
H00B C009 H00C 109.5 . . ?
C00D C009 H00A 109.5 . . ?
C00D C009 H00B 109.5 . . ?
C00D C009 H00C 109.5 . . ?
C007 C00A H00D 110.7 . . ?
C007 C00A H00E 110.7 . . ?
C007 C00A C00D 105.30(17) . . ?
H00D C00A H00E 108.8 . . ?
C00D C00A H00D 110.7 . . ?
C00D C00A H00E 110.7 . . ?
F001 C00B C006 111.72(17) . . ?
F002 C00B F001 106.44(17) . . ?
F002 C00B F003 107.05(18) . . ?
F002 C00B C006 113.21(18) . . ?
F003 C00B F001 105.71(18) . . ?
F003 C00B C006 112.23(17) . . ?
C008 C00C H00F 119.4 . . ?
C008 C00C C00G 121.3(2) . . ?
C00G C00C H00F 119.4 . . ?
C009 C00D C005 112.66(18) . . ?
C009 C00D C00A 109.34(17) . . ?
C00A C00D C005 101.76(16) . . ?
C00E C00D C005 111.17(17) . . ?
C00E C00D C009 109.81(18) . . ?
C00E C00D C00A 111.89(18) . . ?
C00D C00E H00G 109.5 . . ?
C00D C00E H00H 109.5 . . ?
C00D C00E H00I 109.5 . . ?
H00G C00E H00H 109.5 . . ?
H00G C00E H00I 109.5 . . ?
H00H C00E H00I 109.5 . . ?
C008 C00F H00J 119.6 . . ?
C008 C00F C00I 120.8(3) . . ?
C00I C00F H00J 119.6 . . ?
C00C C00G H00K 120.0 . . ?
C00H C00G C00C 120.0(3) . . ?
C00H C00G H00K 120.0 . . ?
C00G C00H H00L 120.2 . . ?
C00I C00H C00G 119.6(3) . . ?
C00I C00H H00L 120.2 . . ?
C00F C00I H00M 119.7 . . ?
C00H C00I C00F 120.7(3) . . ?
C00H C00I H00M 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O004 C007 C00A C00D 156.1(2) . . . . ?
C005 C006 C007 O004 -179.4(2) . . . . ?
C005 C006 C007 C00A 0.1(2) . . . . ?
C005 C006 C00B F001 -64.7(2) . . . . ?
C005 C006 C00B F002 175.17(17) . . . . ?
C005 C006 C00B F003 53.8(2) . . . . ?
C005 C008 C00C C00G -179.6(2) . . . . ?
C005 C008 C00F C00I 179.6(2) . . . . ?
C006 C005 C008 C00C -42.2(3) . . . . ?
C006 C005 C008 C00F 137.4(2) . . . . ?
C006 C005 C00D C009 80.4(2) . . . . ?
C006 C005 C00D C00A -36.61(19) . . . . ?
C006 C005 C00D C00E -155.89(17) . . . . ?
C006 C007 C00A C00D -23.4(2) . . . . ?
C007 C006 C00B F001 52.1(2) . . . . ?
C007 C006 C00B F002 -68.1(2) . . . . ?
C007 C006 C00B F003 170.59(17) . . . . ?
C007 C00A C00D C005 36.7(2) . . . . ?
C007 C00A C00D C009 -82.7(2) . . . . ?
C007 C00A C00D C00E 155.43(18) . . . . ?
C008 C005 C006 C007 152.82(16) . . . . ?
C008 C005 C006 C00B -86.8(2) . . . . ?
C008 C005 C00D C009 -49.3(2) . . . . ?
C008 C005 C00D C00A -166.23(17) . . . . ?
C008 C005 C00D C00E 74.5(2) . . . . ?
C008 C00C C00G C00H -0.5(4) . . . . ?
C008 C00F C00I C00H 0.6(4) . . . . ?
C00B C006 C007 O004 58.8(3) . . . . ?
C00B C006 C007 C00A -121.66(19) . . . . ?
C00C C008 C00F C00I -0.8(3) . . . . ?
C00C C00G C00H C00I 0.2(4) . . . . ?
C00D C005 C006 C007 22.83(19) . . . . ?
C00D C005 C006 C00B 143.20(17) . . . . ?
C00D C005 C008 C00C 82.1(2) . . . . ?
C00D C005 C008 C00F -98.3(2) . . . . ?
C00F C008 C00C C00G 0.8(3) . . . . ?
C00G C00H C00I C00F -0.3(5) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
