# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_0127
_database_code_depnum_ccdc_archive 'CCDC 2244914'
loop_
_audit_author_name
_audit_author_address
tailang
;tailang
China
;
_audit_update_record             
;
2023-02-27 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
_audit_creation_date             2021-11-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H11 F5 N2 O2'
_chemical_formula_sum            'C13 H11 F5 N2 O2'
_chemical_formula_weight         322.24
_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                   8.2006(5)
_cell_length_b                   13.3581(8)
_cell_length_c                   12.1780(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.311(6)
_cell_angle_gamma                90
_cell_volume                     1334.01(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4403
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.7970
_cell_measurement_theta_min      3.3450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8513
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.263
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  39.00   1.00    1.35    --   12.05 -57.00 150.00   98
  2  ω    -17.00  81.00   1.00    1.35    --   12.05  77.00  60.00   98
  3  ω    -11.00  82.00   1.00    1.35    --   12.05  57.00 -60.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0087436000
_diffrn_orient_matrix_UB_12      0.0526807000
_diffrn_orient_matrix_UB_13      -0.0053676000
_diffrn_orient_matrix_UB_21      0.0130361000
_diffrn_orient_matrix_UB_22      0.0040897000
_diffrn_orient_matrix_UB_23      0.0574529000
_diffrn_orient_matrix_UB_31      0.0849679000
_diffrn_orient_matrix_UB_32      -0.0060068000
_diffrn_orient_matrix_UB_33      -0.0077273000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2054
_reflns_number_total             2358
_reflns_odcompleteness_completeness 99.93
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0445P)²+1.1353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1103
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_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 0.3474(2) 0.02272(11) 0.62434(14) 0.0695(5) Uani 1 1 d . . . . .
F2 F 0.11967(18) 0.06996(11) 0.55940(18) 0.0710(6) Uani 1 1 d . . . . .
F3 F 0.3281(3) 0.07527(12) 0.46108(14) 0.0704(5) Uani 1 1 d . . . . .
F4 F 0.33654(16) 0.80482(9) 0.53060(11) 0.0398(4) Uani 1 1 d . . . . .
F5 F 0.09196(19) 0.86515(11) 0.19011(11) 0.0502(4) Uani 1 1 d . . . . .
O1 O 0.33195(19) 0.45696(10) 0.61317(12) 0.0325(4) Uani 1 1 d . . . . .
O2 O 0.06720(17) 0.59923(11) 0.60789(11) 0.0282(3) Uani 1 1 d . . . . .
H2 H 0.076746 0.628853 0.666549 0.042 Uiso 1 1 calc R U . . .
N1 N 0.3836(2) 0.21032(13) 0.69645(14) 0.0276(4) Uani 1 1 d . . . . .
N2 N 0.3949(2) 0.31170(12) 0.70409(13) 0.0256(4) Uani 1 1 d . . . . .
C1 C 0.3313(2) 0.35671(15) 0.61439(16) 0.0250(4) Uani 1 1 d . . . . .
C2 C 0.2760(3) 0.28378(16) 0.54404(18) 0.0282(5) Uani 1 1 d . . . . .
H2A H 0.226(3) 0.2917(17) 0.476(2) 0.032(6) Uiso 1 1 d . . . . .
C3 C 0.3114(2) 0.19508(15) 0.59998(16) 0.0265(5) Uani 1 1 d . . . . .
C4 C 0.2705(3) 0.50407(15) 0.51424(16) 0.0275(5) Uani 1 1 d . . . . .
H4A H 0.179963 0.466077 0.484078 0.033 Uiso 1 1 calc R U . . .
H4B H 0.355510 0.508185 0.459347 0.033 Uiso 1 1 calc R U . . .
C5 C 0.2152(2) 0.60775(15) 0.54747(16) 0.0242(4) Uani 1 1 d . . . . .
H5 H 0.298858 0.638249 0.594479 0.029 Uiso 1 1 calc R U . . .
C6 C 0.1880(2) 0.67366(15) 0.44749(16) 0.0234(4) Uani 1 1 d . . . . .
C7 C 0.2471(2) 0.77029(15) 0.44420(17) 0.0266(5) Uani 1 1 d . . . . .
C8 C 0.2190(3) 0.83591(16) 0.35929(18) 0.0326(5) Uani 1 1 d . . . . .
H8 H 0.261357 0.900496 0.359678 0.039 Uiso 1 1 calc R U . . .
C9 C 0.1253(3) 0.80105(16) 0.27400(17) 0.0320(5) Uani 1 1 d . . . . .
C10 C 0.0637(3) 0.70564(17) 0.26960(17) 0.0326(5) Uani 1 1 d . . . . .
H10 H 0.002361 0.684130 0.209621 0.039 Uiso 1 1 calc R U . . .
C11 C 0.0956(2) 0.64225(16) 0.35726(16) 0.0282(5) Uani 1 1 d . . . . .
H11 H 0.054527 0.577363 0.355923 0.034 Uiso 1 1 calc R U . . .
C12 C 0.4802(3) 0.35855(17) 0.79526(18) 0.0346(5) Uani 1 1 d . . . . .
H12A H 0.441323 0.331163 0.863128 0.052 Uiso 1 1 calc R U . . .
H12B H 0.460720 0.429401 0.793995 0.052 Uiso 1 1 calc R U . . .
H12C H 0.595093 0.346077 0.788978 0.052 Uiso 1 1 calc R U . . .
C13 C 0.2778(3) 0.09123(16) 0.56305(19) 0.0329(5) 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
F1 C13 1.310(3) . ?
F2 C13 1.328(3) . ?
F3 C13 1.328(3) . ?
F4 C7 1.360(2) . ?
F5 C9 1.360(2) . ?
O1 C1 1.339(2) . ?
O1 C4 1.447(2) . ?
O2 H2 0.8200 . ?
O2 C5 1.427(2) . ?
N1 N2 1.361(2) . ?
N1 C3 1.329(3) . ?
N2 C1 1.349(2) . ?
N2 C12 1.451(3) . ?
C1 C2 1.373(3) . ?
C2 H2A 0.93(2) . ?
C2 C3 1.396(3) . ?
C3 C13 1.484(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.513(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.518(3) . ?
C6 C7 1.379(3) . ?
C6 C11 1.396(3) . ?
C7 C8 1.374(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.370(3) . ?
C9 C10 1.372(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(3) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C1 O1 C4 116.27(15) . . ?
C5 O2 H2 109.5 . . ?
C3 N1 N2 104.06(16) . . ?
N1 N2 C12 120.94(16) . . ?
C1 N2 N1 111.23(16) . . ?
C1 N2 C12 127.59(17) . . ?
O1 C1 N2 116.94(17) . . ?
O1 C1 C2 134.75(18) . . ?
N2 C1 C2 108.30(18) . . ?
C1 C2 H2A 128.2(15) . . ?
C1 C2 C3 103.33(18) . . ?
C3 C2 H2A 128.4(15) . . ?
N1 C3 C2 113.07(18) . . ?
N1 C3 C13 119.51(18) . . ?
C2 C3 C13 127.42(19) . . ?
O1 C4 H4A 110.5 . . ?
O1 C4 H4B 110.5 . . ?
O1 C4 C5 106.20(15) . . ?
H4A C4 H4B 108.7 . . ?
C5 C4 H4A 110.5 . . ?
C5 C4 H4B 110.5 . . ?
O2 C5 C4 108.78(16) . . ?
O2 C5 H5 109.1 . . ?
O2 C5 C6 109.78(15) . . ?
C4 C5 H5 109.1 . . ?
C4 C5 C6 111.06(16) . . ?
C6 C5 H5 109.1 . . ?
C7 C6 C5 121.07(17) . . ?
C7 C6 C11 116.58(18) . . ?
C11 C6 C5 122.26(18) . . ?
F4 C7 C6 118.87(18) . . ?
F4 C7 C8 116.95(18) . . ?
C8 C7 C6 124.17(19) . . ?
C7 C8 H8 121.8 . . ?
C9 C8 C7 116.4(2) . . ?
C9 C8 H8 121.8 . . ?
F5 C9 C8 117.7(2) . . ?
F5 C9 C10 118.9(2) . . ?
C8 C9 C10 123.38(19) . . ?
C9 C10 H10 121.0 . . ?
C9 C10 C11 117.99(19) . . ?
C11 C10 H10 121.0 . . ?
C6 C11 H11 119.3 . . ?
C10 C11 C6 121.5(2) . . ?
C10 C11 H11 119.3 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
F1 C13 F2 106.98(19) . . ?
F1 C13 F3 106.5(2) . . ?
F1 C13 C3 113.62(18) . . ?
F2 C13 F3 104.0(2) . . ?
F2 C13 C3 112.96(18) . . ?
F3 C13 C3 112.05(18) . . ?

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
F4 C7 C8 C9 -178.42(18) . . . . ?
F5 C9 C10 C11 -178.38(19) . . . . ?
O1 C1 C2 C3 -178.1(2) . . . . ?
O1 C4 C5 O2 -73.35(19) . . . . ?
O1 C4 C5 C6 165.73(15) . . . . ?
O2 C5 C6 C7 105.4(2) . . . . ?
O2 C5 C6 C11 -71.1(2) . . . . ?
N1 N2 C1 O1 178.58(17) . . . . ?
N1 N2 C1 C2 -0.2(2) . . . . ?
N1 C3 C13 F1 -10.0(3) . . . . ?
N1 C3 C13 F2 112.1(2) . . . . ?
N1 C3 C13 F3 -130.8(2) . . . . ?
N2 N1 C3 C2 0.3(2) . . . . ?
N2 N1 C3 C13 -179.84(18) . . . . ?
N2 C1 C2 C3 0.4(2) . . . . ?
C1 O1 C4 C5 156.13(17) . . . . ?
C1 C2 C3 N1 -0.5(2) . . . . ?
C1 C2 C3 C13 179.7(2) . . . . ?
C2 C3 C13 F1 169.7(2) . . . . ?
C2 C3 C13 F2 -68.1(3) . . . . ?
C2 C3 C13 F3 49.0(3) . . . . ?
C3 N1 N2 C1 -0.1(2) . . . . ?
C3 N1 N2 C12 -174.84(18) . . . . ?
C4 O1 C1 N2 177.13(17) . . . . ?
C4 O1 C1 C2 -4.5(3) . . . . ?
C4 C5 C6 C7 -134.2(2) . . . . ?
C4 C5 C6 C11 49.3(3) . . . . ?
C5 C6 C7 F4 2.7(3) . . . . ?
C5 C6 C7 C8 -176.07(19) . . . . ?
C5 C6 C11 C10 175.97(19) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C7 C6 C11 C10 -0.7(3) . . . . ?
C7 C8 C9 F5 178.34(18) . . . . ?
C7 C8 C9 C10 -1.4(3) . . . . ?
C8 C9 C10 C11 1.3(3) . . . . ?
C9 C10 C11 C6 -0.2(3) . . . . ?
C11 C6 C7 F4 179.39(18) . . . . ?
C11 C6 C7 C8 0.6(3) . . . . ?
C12 N2 C1 O1 -7.1(3) . . . . ?
C12 N2 C1 C2 174.1(2) . . . . ?

_olex2_date_sample_data_collection 2021-11-17
_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 1.215
_oxdiff_exptl_absorpt_empirical_full_min 0.721
