# Supplementary Information (SI) for Green Chemistry.
# 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_huangt1_0229_auto
_database_code_depnum_ccdc_archive 'CCDC 2336872'
loop_
_audit_author_name
_audit_author_address
'Tao Huang'
;Lanzhou University
China
;
_audit_update_record             
;
2024-03-01 deposited with the CCDC.	2024-08-13 downloaded from the CCDC.
;
_audit_creation_date             2024-03-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 F3 N O'
_chemical_formula_sum            'C13 H12 F3 N O'
_chemical_formula_weight         255.24
_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'
N N 0.0061 0.0033 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.6674(5)
_cell_length_b                   10.0950(4)
_cell_length_c                   11.8549(6)
_cell_angle_alpha                90
_cell_angle_beta                 115.445(6)
_cell_angle_gamma                90
_cell_volume                     1152.79(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7146
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.7730
_cell_measurement_theta_min      2.7620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.810
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11931
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.810
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.707
_diffrn_reflns_theta_min         2.152
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.810
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  15.00   0.50    0.31    --    4.05 -99.00 -60.00   54
  2  ω    -14.00  36.00   0.50    0.31    --    4.05 -99.00  60.00  100
  3  ω    -27.00  33.00   0.50    0.31    --    4.05 -93.00 172.00  120
  4  ω     48.00  75.00   0.50    0.31    --    4.05  37.00-120.00   54
  5  ω    -22.00  34.00   0.50    0.31    --    4.05  93.00 -74.00  112
  6  ω    -18.00  60.00   0.50    0.31    --   -6.39  37.00-150.00  156
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0479115000
_diffrn_orient_matrix_UB_12      -0.0426351000
_diffrn_orient_matrix_UB_13      -0.0088032000
_diffrn_orient_matrix_UB_21      -0.0116856000
_diffrn_orient_matrix_UB_22      -0.0489587000
_diffrn_orient_matrix_UB_23      0.0373404000
_diffrn_orient_matrix_UB_31      -0.0546819000
_diffrn_orient_matrix_UB_32      -0.0268995000
_diffrn_orient_matrix_UB_33      -0.0540020000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2438
_reflns_number_total             2899
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.049
_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)+(0.0508P)²+0.5237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1118
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00B), C19(H19A,H19B), C20(H20A,H20B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 N16(H16), C6(H6), C7(H7), C11(H11)
;
_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 0.74678(11) 0.78145(10) 0.02270(8) 0.0418(3) Uani 1 1 d . . . . .
F3 F 0.70372(11) 0.57517(10) 0.00620(8) 0.0425(3) Uani 1 1 d . . . . .
F4 F 0.91557(11) 0.64517(14) 0.08685(9) 0.0569(3) Uani 1 1 d . . . . .
O15 O 0.49719(9) 0.48104(9) 0.33921(8) 0.0229(2) Uani 1 1 d . . . . .
N16 N 0.65272(11) 0.58436(10) 0.51902(10) 0.0204(2) Uani 1 1 d . . . . .
H16 H 0.612859 0.561962 0.567622 0.025 Uiso 1 1 calc R U . . .
C00I C 0.87784(18) 0.63124(17) 0.78836(13) 0.0375(4) Uani 1 1 d . . . . .
H00A H 0.837349 0.554726 0.813279 0.045 Uiso 1 1 calc R U . . .
H00B H 0.966997 0.654944 0.859144 0.045 Uiso 1 1 calc R U . . .
C2 C 0.79058(15) 0.66626(15) 0.08228(13) 0.0270(3) Uani 1 1 d . . . . .
C5 C 0.79184(14) 0.66733(13) 0.20918(12) 0.0216(3) Uani 1 1 d . . . . .
C6 C 0.69115(13) 0.59881(12) 0.23081(11) 0.0203(3) Uani 1 1 d . . . . .
H6 H 0.621291 0.548655 0.166706 0.024 Uiso 1 1 calc R U . . .
C7 C 0.89471(14) 0.74089(14) 0.30378(12) 0.0252(3) Uani 1 1 d . . . . .
H7 H 0.961881 0.787687 0.286677 0.030 Uiso 1 1 calc R U . . .
C8 C 0.69683(13) 0.60662(12) 0.34954(11) 0.0184(2) Uani 1 1 d . . . . .
C11 C 0.89930(14) 0.74595(14) 0.42251(12) 0.0251(3) Uani 1 1 d . . . . .
H11 H 0.969551 0.795092 0.487255 0.030 Uiso 1 1 calc R U . . .
C12 C 0.60221(13) 0.54786(12) 0.39855(11) 0.0188(2) Uani 1 1 d . . . . .
C13 C 0.79899(13) 0.67763(12) 0.44472(11) 0.0196(3) Uani 1 1 d . . . . .
C17 C 0.78021(13) 0.66491(12) 0.56333(11) 0.0195(3) Uani 1 1 d . . . . .
C19 C 0.76323(15) 0.79400(13) 0.62359(12) 0.0240(3) Uani 1 1 d . . . . .
H19A H 0.671109 0.834339 0.574144 0.029 Uiso 1 1 calc R U . . .
H19B H 0.836350 0.858697 0.631638 0.029 Uiso 1 1 calc R U . . .
C20 C 0.90088(14) 0.59678(15) 0.67219(12) 0.0272(3) Uani 1 1 d . . . . .
H20A H 0.991389 0.631088 0.680497 0.033 Uiso 1 1 calc R U . . .
H20B H 0.898264 0.499716 0.659418 0.033 Uiso 1 1 calc R U . . .
C23 C 0.77767(16) 0.74939(14) 0.75236(13) 0.0286(3) Uani 1 1 d . . . . .
H23A H 0.686466 0.722541 0.748076 0.034 Uiso 1 1 calc R U . . .
H23B H 0.815736 0.821822 0.814120 0.034 Uiso 1 1 calc R 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 C2 1.3363(17) . ?
F3 C2 1.3414(17) . ?
F4 C2 1.3282(17) . ?
O15 C12 1.2360(15) . ?
N16 H16 0.8800 . ?
N16 C12 1.3433(16) . ?
N16 C17 1.4741(15) . ?
C00I H00A 0.9900 . ?
C00I H00B 0.9900 . ?
C00I C20 1.539(2) . ?
C00I C23 1.535(2) . ?
C2 C5 1.4987(17) . ?
C5 C6 1.3908(17) . ?
C5 C7 1.3985(19) . ?
C6 H6 0.9500 . ?
C6 C8 1.3849(17) . ?
C7 H7 0.9500 . ?
C7 C11 1.3882(18) . ?
C8 C12 1.4873(17) . ?
C8 C13 1.3849(17) . ?
C11 H11 0.9500 . ?
C11 C13 1.3900(18) . ?
C13 C17 1.5086(16) . ?
C17 C19 1.5338(18) . ?
C17 C20 1.5388(18) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C23 1.5345(18) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?

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
C12 N16 H16 122.7 . . ?
C12 N16 C17 114.67(10) . . ?
C17 N16 H16 122.7 . . ?
H00A C00I H00B 108.6 . . ?
C20 C00I H00A 110.4 . . ?
C20 C00I H00B 110.4 . . ?
C23 C00I H00A 110.4 . . ?
C23 C00I H00B 110.4 . . ?
C23 C00I C20 106.66(11) . . ?
F1 C2 F3 104.92(11) . . ?
F1 C2 C5 112.01(11) . . ?
F3 C2 C5 112.68(11) . . ?
F4 C2 F1 106.13(12) . . ?
F4 C2 F3 107.99(12) . . ?
F4 C2 C5 112.60(11) . . ?
C6 C5 C2 120.45(12) . . ?
C6 C5 C7 121.22(11) . . ?
C7 C5 C2 118.31(11) . . ?
C5 C6 H6 121.3 . . ?
C8 C6 C5 117.32(12) . . ?
C8 C6 H6 121.3 . . ?
C5 C7 H7 119.8 . . ?
C11 C7 C5 120.42(12) . . ?
C11 C7 H7 119.8 . . ?
C6 C8 C12 129.32(11) . . ?
C6 C8 C13 122.21(11) . . ?
C13 C8 C12 108.46(10) . . ?
C7 C11 H11 120.7 . . ?
C7 C11 C13 118.63(12) . . ?
C13 C11 H11 120.7 . . ?
O15 C12 N16 127.32(11) . . ?
O15 C12 C8 126.63(11) . . ?
N16 C12 C8 106.05(10) . . ?
C8 C13 C11 120.19(11) . . ?
C8 C13 C17 110.01(10) . . ?
C11 C13 C17 129.80(12) . . ?
N16 C17 C13 100.74(9) . . ?
N16 C17 C19 111.05(10) . . ?
N16 C17 C20 111.32(10) . . ?
C13 C17 C19 116.83(10) . . ?
C13 C17 C20 114.93(11) . . ?
C19 C17 C20 102.29(10) . . ?
C17 C19 H19A 111.1 . . ?
C17 C19 H19B 111.1 . . ?
C17 C19 C23 103.45(11) . . ?
H19A C19 H19B 109.0 . . ?
C23 C19 H19A 111.1 . . ?
C23 C19 H19B 111.1 . . ?
C00I C20 H20A 110.8 . . ?
C00I C20 H20B 110.8 . . ?
C17 C20 C00I 104.58(11) . . ?
C17 C20 H20A 110.8 . . ?
C17 C20 H20B 110.8 . . ?
H20A C20 H20B 108.9 . . ?
C00I C23 H23A 110.7 . . ?
C00I C23 H23B 110.7 . . ?
C19 C23 C00I 105.37(11) . . ?
C19 C23 H23A 110.7 . . ?
C19 C23 H23B 110.7 . . ?
H23A C23 H23B 108.8 . . ?

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 C2 C5 C6 105.83(14) . . . . ?
F1 C2 C5 C7 -72.89(16) . . . . ?
F3 C2 C5 C6 -12.19(18) . . . . ?
F3 C2 C5 C7 169.09(12) . . . . ?
F4 C2 C5 C6 -134.64(14) . . . . ?
F4 C2 C5 C7 46.64(18) . . . . ?
N16 C17 C19 C23 76.75(13) . . . . ?
N16 C17 C20 C00I -82.00(13) . . . . ?
C2 C5 C6 C8 -178.56(12) . . . . ?
C2 C5 C7 C11 179.37(13) . . . . ?
C5 C6 C8 C12 178.10(12) . . . . ?
C5 C6 C8 C13 -0.95(18) . . . . ?
C5 C7 C11 C13 -0.6(2) . . . . ?
C6 C5 C7 C11 0.7(2) . . . . ?
C6 C8 C12 O15 -1.2(2) . . . . ?
C6 C8 C12 N16 179.99(12) . . . . ?
C6 C8 C13 C11 1.00(19) . . . . ?
C6 C8 C13 C17 -178.56(11) . . . . ?
C7 C5 C6 C8 0.12(19) . . . . ?
C7 C11 C13 C8 -0.2(2) . . . . ?
C7 C11 C13 C17 179.28(12) . . . . ?
C8 C13 C17 N16 -2.55(13) . . . . ?
C8 C13 C17 C19 -122.92(12) . . . . ?
C8 C13 C17 C20 117.20(12) . . . . ?
C11 C13 C17 N16 177.95(13) . . . . ?
C11 C13 C17 C19 57.57(19) . . . . ?
C11 C13 C17 C20 -62.30(18) . . . . ?
C12 N16 C17 C13 2.09(13) . . . . ?
C12 N16 C17 C19 126.51(11) . . . . ?
C12 N16 C17 C20 -120.22(12) . . . . ?
C12 C8 C13 C11 -178.23(12) . . . . ?
C12 C8 C13 C17 2.21(14) . . . . ?
C13 C8 C12 O15 177.99(12) . . . . ?
C13 C8 C12 N16 -0.86(14) . . . . ?
C13 C17 C19 C23 -168.51(11) . . . . ?
C13 C17 C20 C00I 164.29(11) . . . . ?
C17 N16 C12 O15 -179.73(12) . . . . ?
C17 N16 C12 C8 -0.89(14) . . . . ?
C17 C19 C23 C00I 31.46(14) . . . . ?
C19 C17 C20 C00I 36.66(13) . . . . ?
C20 C00I C23 C19 -8.60(16) . . . . ?
C20 C17 C19 C23 -42.09(12) . . . . ?
C23 C00I C20 C17 -17.46(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.169
_oxdiff_exptl_absorpt_empirical_full_min 0.803
