# 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_hwq01_a
_database_code_depnum_ccdc_archive 'CCDC 2141492'
loop_
_audit_author_name
_audit_author_address
'Wanqiao Huang'
;Northeast Normal University
China
;
_audit_update_record             
;
2022-01-12 deposited with the CCDC.	2022-03-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT972_hwq01_a             
;
PROBLEM: Check Calcd Resid. Dens.  0.93Ang From I1             -3.45 eA-3
RESPONSE: It is due to the disorder. 
;
_vrf_PLAT972_hwq01_a_2           
;
PROBLEM: Check Calcd Resid. Dens.  0.94Ang From I1             -3.12 eA-3
RESPONSE: It is due to the disorder. 
;
_vrf_PLAT972_hwq01_a_3           
;
PROBLEM: Check Calcd Resid. Dens.  1.10Ang From I1             -3.00 eA-3
RESPONSE: It is due to the disorder. 
;
_vrf_PLAT972_hwq01_a_4           
;
PROBLEM: Check Calcd Resid. Dens.  1.07Ang From I1             -2.99 eA-3
RESPONSE: It is due to the disorder. 
;
# Added during the CSD deposition process: Wednesday 12 January 2022 06:56 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 F3 I N O2'
_chemical_formula_sum            'C14 H15 F3 I N O2'
_chemical_formula_weight         413.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.7369(15)
_cell_length_b                   18.391(3)
_cell_length_c                   11.3341(18)
_cell_angle_alpha                90
_cell_angle_beta                 110.989(9)
_cell_angle_gamma                90
_cell_volume                     1700.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    5441
_cell_measurement_theta_min      4.81
_cell_measurement_theta_max      63.87

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    15.113
_shelx_estimated_absorpt_T_min   0.136
_shelx_estimated_absorpt_T_max   0.343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.073
_exptl_absorpt_correction_T_max  0.257
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            6695
_diffrn_reflns_av_unetI/netI     0.0773
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.809
_diffrn_reflns_theta_max         62.497
_diffrn_reflns_theta_full        62.497
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             2602
_reflns_number_gt                2005
_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-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXL'
_computing_publication_material  'Bruker SHELXL'
_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)+(0.2000P)²] 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         2602
_refine_ls_number_parameters     190
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1406
_refine_ls_R_factor_gt           0.1127
_refine_ls_wR_factor_ref         0.3339
_refine_ls_wR_factor_gt          0.3090
_refine_ls_goodness_of_fit_ref   1.342
_refine_ls_restrained_S_all      1.352
_refine_ls_shift/su_max          0.084
_refine_ls_shift/su_mean         0.013

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 0.5560(11) 0.6391(7) 0.3108(10) 0.034(3) Uani 1 1 d . . . . .
C2 C 0.6734(13) 0.6797(8) 0.4007(12) 0.047(3) Uani 1 1 d . . . . .
H2A H 0.741722 0.710609 0.377115 0.057 Uiso 1 1 calc R U . . .
C3 C 0.6889(15) 0.6745(8) 0.5240(13) 0.054(3) Uani 1 1 d . . . . .
H3A H 0.768977 0.701939 0.583859 0.064 Uiso 1 1 calc R U . . .
C4 C 0.5898(14) 0.6299(6) 0.5630(12) 0.042(3) Uani 1 1 d . . . . .
C5 C 0.4672(13) 0.5897(7) 0.4693(11) 0.043(3) Uani 1 1 d . . . . .
H5A H 0.398828 0.558253 0.491795 0.051 Uiso 1 1 calc R U . . .
C6 C 0.4508(12) 0.5977(7) 0.3456(11) 0.038(3) Uani 1 1 d . . . . .
H6A H 0.365183 0.574127 0.283511 0.046 Uiso 1 1 calc R U . . .
C7 C 0.4121(12) 0.6855(8) 0.0911(11) 0.046(3) Uani 1 1 d . . . . .
H7A H 0.408176 0.688012 0.008085 0.056 Uiso 1 1 calc R U . . .
C8 C 0.2993(12) 0.7194(7) 0.1200(13) 0.051(3) Uani 1 1 d . . . . .
H8A H 0.302132 0.718248 0.202734 0.061 Uiso 1 1 calc R U . . .
C9 C 0.1648(15) 0.7602(10) 0.0212(16) 0.067(4) Uani 1 1 d . . . . .
C10 C 0.6425(14) 0.6088(7) 0.1318(11) 0.042(3) Uani 1 1 d . . . . .
C11 C 0.8761(13) 0.5241(7) 0.2015(11) 0.043(3) Uani 1 1 d . . . . .
C12 C 0.970(2) 0.4959(12) 0.3300(16) 0.095(6) Uani 1 1 d . . . . .
H12A H 1.055138 0.464112 0.326265 0.142 Uiso 1 1 calc R U . . .
H12B H 1.017482 0.535844 0.385509 0.142 Uiso 1 1 calc R U . . .
H12C H 0.897381 0.469521 0.361212 0.142 Uiso 1 1 calc R U . . .
C13 C 0.9827(15) 0.5694(10) 0.1484(17) 0.079(5) Uani 1 1 d . . . . .
H13A H 1.062908 0.538612 0.133658 0.119 Uiso 1 1 calc R U . . .
H13B H 0.915170 0.591309 0.070189 0.119 Uiso 1 1 calc R U . . .
H13C H 1.037271 0.606686 0.207759 0.119 Uiso 1 1 calc R U . . .
C14 C 0.7894(19) 0.4650(10) 0.1052(19) 0.087(5) Uani 1 1 d . . . . .
H14A H 0.869724 0.434429 0.090332 0.130 Uiso 1 1 calc R U . . .
H14B H 0.721806 0.436131 0.137753 0.130 Uiso 1 1 calc R U . . .
H14C H 0.722309 0.487368 0.027352 0.130 Uiso 1 1 calc R U . . .
F1 F 0.1833(14) 0.7588(8) -0.0887(11) 0.126(5) Uani 1 1 d . . . . .
F2 F 0.0215(10) 0.7276(7) -0.0003(15) 0.130(5) Uani 1 1 d . U . . .
F3 F 0.1532(15) 0.8262(6) 0.0442(14) 0.132(5) Uani 1 1 d . . . . .
I1 I 0.61466(11) 0.61841(5) 0.75161(7) 0.0598(6) Uani 1 1 d . . . . .
N1 N 0.5388(10) 0.6455(6) 0.1780(8) 0.038(2) Uani 1 1 d . . . . .
O1 O 0.6319(13) 0.6108(6) 0.0227(9) 0.072(3) Uani 1 1 d . . . . .
O2 O 0.7529(9) 0.5708(5) 0.2243(7) 0.047(2) 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 C6 1.357(18) . ?
C1 C2 1.378(16) . ?
C1 N1 1.463(15) . ?
C2 C3 1.357(18) . ?
C2 H2A 0.9300 . ?
C3 C4 1.376(18) . ?
C3 H3A 0.9300 . ?
C4 C5 1.417(17) . ?
C4 I1 2.080(13) . ?
C5 C6 1.366(17) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.303(18) . ?
C7 N1 1.398(14) . ?
C7 H7A 0.9300 . ?
C8 C9 1.502(17) . ?
C8 H8A 0.9300 . ?
C9 F3 1.25(2) . ?
C9 F1 1.313(19) . ?
C9 F2 1.331(18) . ?
C10 O1 1.207(16) . ?
C10 O2 1.339(13) . ?
C10 N1 1.375(16) . ?
C11 O2 1.472(13) . ?
C11 C12 1.485(19) . ?
C11 C13 1.525(19) . ?
C11 C14 1.53(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C6 C1 C2 119.4(11) . . ?
C6 C1 N1 120.9(9) . . ?
C2 C1 N1 119.5(11) . . ?
C3 C2 C1 119.7(12) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 122.1(12) . . ?
C2 C3 H3A 119.0 . . ?
C4 C3 H3A 119.0 . . ?
C3 C4 C5 117.6(12) . . ?
C3 C4 I1 123.0(9) . . ?
C5 C4 I1 119.3(9) . . ?
C6 C5 C4 119.1(11) . . ?
C6 C5 H5A 120.4 . . ?
C4 C5 H5A 120.4 . . ?
C1 C6 C5 121.7(10) . . ?
C1 C6 H6A 119.1 . . ?
C5 C6 H6A 119.1 . . ?
C8 C7 N1 123.6(12) . . ?
C8 C7 H7A 118.2 . . ?
N1 C7 H7A 118.2 . . ?
C7 C8 C9 120.8(13) . . ?
C7 C8 H8A 119.6 . . ?
C9 C8 H8A 119.6 . . ?
F3 C9 F1 105.2(15) . . ?
F3 C9 F2 109.5(14) . . ?
F1 C9 F2 104.2(16) . . ?
F3 C9 C8 115.5(15) . . ?
F1 C9 C8 111.6(13) . . ?
F2 C9 C8 110.2(13) . . ?
O1 C10 O2 126.0(11) . . ?
O1 C10 N1 123.8(11) . . ?
O2 C10 N1 110.3(10) . . ?
O2 C11 C12 102.3(11) . . ?
O2 C11 C13 109.8(11) . . ?
C12 C11 C13 112.2(12) . . ?
O2 C11 C14 109.4(9) . . ?
C12 C11 C14 114.1(14) . . ?
C13 C11 C14 108.8(12) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.4 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.4 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 N1 C7 116.9(10) . . ?
C10 N1 C1 120.9(9) . . ?
C7 N1 C1 122.1(9) . . ?
C10 O2 C11 122.3(9) . . ?

_refine_diff_density_max         1.087
_refine_diff_density_min         -3.500
_refine_diff_density_rms         0.320

