# 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_230821_2f_beta_oh_0m
_database_code_depnum_ccdc_archive 'CCDC 2326945'
loop_
_audit_author_name
_audit_author_address
F
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2024-01-20 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;
_audit_creation_date             2023-08-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 F4 N O2'
_chemical_formula_sum            'C12 H13 F4 N O2'
_chemical_formula_weight         279.23
_chemical_absolute_configuration ad
_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 0.0137 0.0067 '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 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   6.3753(5)
_cell_length_b                   7.7643(6)
_cell_length_c                   13.1312(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.979(3)
_cell_angle_gamma                90
_cell_volume                     643.70(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9227
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.927
_cell_measurement_theta_min      2.957
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.907
_exptl_absorpt_coefficient_mu    0.764
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1723 before and 0.0949 after correction.
The Ratio of minimum to maximum transmission is 0.8778.
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    1.441
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15240
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         61.108
_diffrn_reflns_theta_min         5.774
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.24954300000000001
_diffrn_source_voltage           69.9
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                2746
_reflns_number_total             2915
_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 (?, 2016)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1180 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2915
_refine_ls_number_restraints     76
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.065
_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)+(0.0613P)²+0.0891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1008
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 F4-C12 \\sim F4A-C12
 with sigma of 0.02
 F3-C12 \\sim F3A-C12
 with sigma of 0.02
 F2-C12 \\sim F2A-C12
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F2 \\sim F2A \\sim F3 \\sim F3A \\sim F4 \\sim F4A \\sim C12: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(F2A)=Sof(F3A)=Sof(F4A)=1-FVAR(1)
 Sof(F2)=Sof(F3)=Sof(F4)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5)
5.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
5.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.76849(19) 0.72982(15) 0.48653(9) 0.0333(3) Uani 1 1 d . . . . .
O1 O 1.0429(2) 0.5843(2) 0.63561(11) 0.0379(4) Uani 1 1 d . . . . .
N1 N 0.7641(2) 0.4834(2) 0.70550(12) 0.0314(4) Uani 1 1 d . . . . .
C1 C 0.8968(4) 0.4632(4) 0.80477(17) 0.0460(6) Uani 1 1 d . . . . .
H1A H 0.911253 0.340560 0.821887 0.069 Uiso 1 1 calc R U . . .
H1B H 0.831016 0.523060 0.857955 0.069 Uiso 1 1 calc R U . . .
H1C H 1.037009 0.512536 0.801094 0.069 Uiso 1 1 calc R U . . .
F2 F 0.469(2) 0.568(3) -0.0360(8) 0.094(3) Uani 0.45(3) 1 d D U P A 1
F2A F 0.256(3) 0.6608(14) 0.0180(10) 0.099(4) Uani 0.55(3) 1 d D U P A 2
O2 O 0.7415(2) 0.27133(17) 0.48705(11) 0.0300(3) Uani 1 1 d . . . . .
H2 H 0.816391 0.195933 0.463693 0.045 Uiso 1 1 calc R U . . .
C2 C 0.5440(3) 0.4289(4) 0.70059(17) 0.0416(5) Uani 1 1 d . . . . .
H2A H 0.454422 0.529631 0.707389 0.062 Uiso 1 1 calc R U . . .
H2B H 0.531119 0.347864 0.756624 0.062 Uiso 1 1 calc R U . . .
H2C H 0.498514 0.372429 0.634443 0.062 Uiso 1 1 calc R U . . .
F3 F 0.259(3) 0.3702(14) -0.0029(12) 0.101(5) Uani 0.45(3) 1 d D U P A 1
F3A F 0.4612(17) 0.485(2) -0.0394(6) 0.088(3) Uani 0.55(3) 1 d D U P A 2
C3 C 0.8533(3) 0.5437(2) 0.62695(14) 0.0278(4) Uani 1 1 d . . . . .
F4 F 0.183(3) 0.619(3) 0.0251(12) 0.097(4) Uani 0.45(3) 1 d D U P A 1
F4A F 0.193(2) 0.3918(19) 0.0117(9) 0.100(3) Uani 0.55(3) 1 d D U P A 2
C4 C 0.7198(3) 0.5668(3) 0.52156(14) 0.0262(4) Uani 1 1 d . . . . .
H4 H 0.565287 0.557245 0.526942 0.031 Uiso 1 1 calc R U . . .
C5 C 0.7852(3) 0.4345(2) 0.44627(14) 0.0264(4) Uani 1 1 d . . . . .
H5 H 0.941055 0.444372 0.444625 0.032 Uiso 1 1 calc R U . . .
C6 C 0.6696(3) 0.4604(2) 0.33835(13) 0.0277(4) Uani 1 1 d . . . . .
C7 C 0.7745(3) 0.5256(3) 0.26115(16) 0.0395(5) Uani 1 1 d . . . . .
H7 H 0.918825 0.558766 0.276663 0.047 Uiso 1 1 calc R U . . .
C8 C 0.6711(4) 0.5431(4) 0.16120(17) 0.0471(6) Uani 1 1 d . . . . .
H8 H 0.743883 0.588334 0.108703 0.057 Uiso 1 1 calc R U . . .
C9 C 0.4612(4) 0.4939(3) 0.13911(16) 0.0406(5) Uani 1 1 d . . . . .
C10 C 0.3526(4) 0.4310(3) 0.21596(17) 0.0398(5) Uani 1 1 d . . . . .
H10 H 0.207848 0.398982 0.200523 0.048 Uiso 1 1 calc R U . . .
C11 C 0.4573(3) 0.4155(3) 0.31545(16) 0.0348(4) Uani 1 1 d . . . . .
H11 H 0.383159 0.373740 0.368392 0.042 Uiso 1 1 calc R U . . .
C12 C 0.3446(5) 0.5110(4) 0.03188(19) 0.0568(7) Uani 1 1 d D U . . .


_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 C4 1.396(2) . ?
O1 C3 1.239(2) . ?
N1 C1 1.461(2) . ?
N1 C2 1.459(3) . ?
N1 C3 1.330(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
F2 C12 1.349(12) . ?
F2A C12 1.295(10) . ?
O2 H2 0.8400 . ?
O2 C5 1.418(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
F3 C12 1.278(11) . ?
F3A C12 1.289(9) . ?
C3 C4 1.531(2) . ?
F4 C12 1.322(12) . ?
F4A C12 1.337(11) . ?
C4 H4 1.0000 . ?
C4 C5 1.523(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.517(2) . ?
C6 C7 1.385(3) . ?
C6 C11 1.390(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.391(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(4) . ?
C9 C10 1.389(4) . ?
C9 C12 1.504(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(3) . ?
C11 H11 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
C2 N1 C1 116.27(17) . . ?
C3 N1 C1 118.24(17) . . ?
C3 N1 C2 125.45(16) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C5 O2 H2 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O1 C3 N1 122.33(17) . . ?
O1 C3 C4 117.77(16) . . ?
N1 C3 C4 119.90(16) . . ?
F1 C4 C3 106.43(15) . . ?
F1 C4 H4 110.9 . . ?
F1 C4 C5 107.70(14) . . ?
C3 C4 H4 110.9 . . ?
C5 C4 C3 109.86(15) . . ?
C5 C4 H4 110.9 . . ?
O2 C5 C4 105.76(14) . . ?
O2 C5 H5 108.9 . . ?
O2 C5 C6 112.07(15) . . ?
C4 C5 H5 108.9 . . ?
C6 C5 C4 112.07(14) . . ?
C6 C5 H5 108.9 . . ?
C7 C6 C5 120.73(17) . . ?
C7 C6 C11 119.21(18) . . ?
C11 C6 C5 120.05(17) . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.8(2) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.3(2) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 120.66(19) . . ?
C8 C9 C12 120.7(2) . . ?
C10 C9 C12 118.7(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
C6 C11 H11 119.7 . . ?
C10 C11 C6 120.6(2) . . ?
C10 C11 H11 119.7 . . ?
F2 C12 C9 112.8(6) . . ?
F2A C12 F4A 107.8(8) . . ?
F2A C12 C9 111.1(6) . . ?
F3 C12 F2 107.9(9) . . ?
F3 C12 F4 103.2(9) . . ?
F3 C12 C9 113.0(7) . . ?
F3A C12 F2A 108.7(8) . . ?
F3A C12 F4A 102.9(7) . . ?
F3A C12 C9 114.0(5) . . ?
F4 C12 F2 105.7(9) . . ?
F4 C12 C9 113.5(7) . . ?
F4A C12 C9 112.0(5) . . ?

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
F1 C4 C5 O2 177.56(14) . . . . ?
F1 C4 C5 C6 -60.04(18) . . . . ?
O1 C3 C4 F1 -45.9(2) . . . . ?
O1 C3 C4 C5 70.4(2) . . . . ?
N1 C3 C4 F1 133.48(18) . . . . ?
N1 C3 C4 C5 -110.18(19) . . . . ?
C1 N1 C3 O1 -0.6(3) . . . . ?
C1 N1 C3 C4 180.0(2) . . . . ?
O2 C5 C6 C7 -133.8(2) . . . . ?
O2 C5 C6 C11 45.0(2) . . . . ?
C2 N1 C3 O1 -178.3(2) . . . . ?
C2 N1 C3 C4 2.4(3) . . . . ?
C3 C4 C5 O2 62.03(17) . . . . ?
C3 C4 C5 C6 -175.57(16) . . . . ?
C4 C5 C6 C7 107.5(2) . . . . ?
C4 C5 C6 C11 -73.7(2) . . . . ?
C5 C6 C7 C8 177.4(2) . . . . ?
C5 C6 C11 C10 -176.99(19) . . . . ?
C6 C7 C8 C9 -0.2(4) . . . . ?
C7 C6 C11 C10 1.8(3) . . . . ?
C7 C8 C9 C10 1.4(4) . . . . ?
C7 C8 C9 C12 -180.0(2) . . . . ?
C8 C9 C10 C11 -0.9(4) . . . . ?
C8 C9 C12 F2 3.3(11) . . . . ?
C8 C9 C12 F2A -89.1(10) . . . . ?
C8 C9 C12 F3 126.0(11) . . . . ?
C8 C9 C12 F3A 34.0(10) . . . . ?
C8 C9 C12 F4 -116.9(13) . . . . ?
C8 C9 C12 F4A 150.3(9) . . . . ?
C9 C10 C11 C6 -0.7(3) . . . . ?
C10 C9 C12 F2 -178.0(11) . . . . ?
C10 C9 C12 F2A 89.5(10) . . . . ?
C10 C9 C12 F3 -55.3(11) . . . . ?
C10 C9 C12 F3A -147.3(9) . . . . ?
C10 C9 C12 F4 61.8(13) . . . . ?
C10 C9 C12 F4A -31.0(9) . . . . ?
C11 C6 C7 C8 -1.3(3) . . . . ?
C12 C9 C10 C11 -179.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
