# 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 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_1
_audit_block_doi                 10.5517/ccdc.csd.cc2c18xm
_database_code_depnum_ccdc_archive 'CCDC 2175980'
loop_
_audit_author_name
_audit_author_address
'Ningbo Li'
;The Cambridge Crystallographic Data Centre 
China
;
_audit_update_record             
;
2022-05-31 deposited with the CCDC.	2022-11-22 downloaded from the CCDC.
;
_audit_creation_date             2022-01-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H6 F7 N O2'
_chemical_formula_sum            'C12 H6 F7 N O2'
_chemical_formula_weight         329.18
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2140(12)
_cell_length_b                   7.4875(12)
_cell_length_c                   11.7137(18)
_cell_angle_alpha                80.950(5)
_cell_angle_beta                 85.782(5)
_cell_angle_gamma                80.900(5)
_cell_volume                     616.20(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4715
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.90
_cell_measurement_theta_min      3.07
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.929
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0849 before and 0.0586 after correction.
The Ratio of minimum to maximum transmission is 0.8767.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12962
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.571
_diffrn_reflns_theta_min         3.069
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1767
_reflns_number_total             2850
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2850
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0604
_refine_ls_restrained_S_all      1.021
_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)+(0.1006P)²+0.2153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1639
_refine_ls_wR_factor_ref         0.1913
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Rigid bond restraints
 F2, C1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C11(H11)
3.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
F7 F 0.5624(3) 0.3701(2) 0.14309(15) 0.0739(5) Uani 1 1 d . . . . .
F5 F 0.2097(3) 0.4408(2) 0.08057(16) 0.0818(6) Uani 1 1 d . . . . .
F6 F 0.5581(3) 0.0802(2) 0.17356(16) 0.0776(6) Uani 1 1 d . . . . .
F4 F 0.4064(3) 0.2625(3) -0.02094(14) 0.0861(6) Uani 1 1 d . . . . .
F1 F 0.2463(3) -0.0284(2) 0.08639(19) 0.0950(7) Uani 1 1 d . . . . .
O2 O 0.2662(3) 0.1000(2) 0.48369(17) 0.0646(6) Uani 1 1 d . . . . .
F3 F 0.0654(4) 0.1909(3) -0.00861(19) 0.1074(8) Uani 1 1 d . . . . .
O1 O 0.3332(4) -0.0512(2) 0.3381(2) 0.0878(8) Uani 1 1 d . . . . .
N1 N 0.3611(3) 0.5852(2) 0.28316(18) 0.0502(5) Uani 1 1 d . . . . .
H1A H 0.399062 0.590884 0.211527 0.060 Uiso 1 1 calc R . . . .
H1B H 0.338602 0.683115 0.314745 0.060 Uiso 1 1 calc R . . . .
F2 F 0.0495(3) 0.1518(3) 0.17911(19) 0.0904(6) Uani 1 1 d . U . . .
C8 C 0.3370(3) 0.4249(3) 0.3451(2) 0.0389(5) Uani 1 1 d . . . . .
C7 C 0.2710(3) 0.4237(3) 0.4653(2) 0.0410(5) Uani 1 1 d . . . . .
C3 C 0.4478(4) 0.2420(3) 0.1805(2) 0.0535(7) Uani 1 1 d . . . . .
C9 C 0.2376(3) 0.5808(3) 0.5203(2) 0.0505(6) Uani 1 1 d . . . . .
H9 H 0.256380 0.693177 0.478303 0.061 Uiso 1 1 calc R . . . .
C4 C 0.3699(3) 0.2594(3) 0.3014(2) 0.0453(6) Uani 1 1 d . . . . .
C5 C 0.3253(4) 0.0952(3) 0.3706(3) 0.0575(7) Uani 1 1 d . . . . .
C6 C 0.2407(3) 0.2594(3) 0.5312(2) 0.0508(6) Uani 1 1 d . . . . .
C2 C 0.3083(5) 0.2708(4) 0.0824(2) 0.0638(8) Uani 1 1 d . . . . .
C10 C 0.1787(4) 0.5711(5) 0.6330(3) 0.0659(8) Uani 1 1 d . . . . .
H10 H 0.157676 0.676275 0.667887 0.079 Uiso 1 1 calc R . . . .
C1 C 0.1655(5) 0.1426(5) 0.0860(3) 0.0761(9) Uani 1 1 d . U . . .
C12 C 0.1801(4) 0.2476(5) 0.6462(3) 0.0700(8) Uani 1 1 d . . . . .
H12 H 0.160348 0.135923 0.688838 0.084 Uiso 1 1 calc R . . . .
C11 C 0.1495(4) 0.4047(5) 0.6965(3) 0.0760(10) Uani 1 1 d . . . . .
H11 H 0.108750 0.399021 0.774021 0.091 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
F7 C3 1.364(3) . ?
F5 C2 1.354(3) . ?
F6 C3 1.350(3) . ?
F4 C2 1.362(3) . ?
F1 C1 1.320(4) . ?
O2 C5 1.366(3) . ?
O2 C6 1.376(3) . ?
F3 C1 1.338(4) . ?
O1 C5 1.207(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C8 1.330(3) . ?
F2 C1 1.328(4) . ?
C8 C7 1.452(3) . ?
C8 C4 1.394(3) . ?
C7 C9 1.407(3) . ?
C7 C6 1.385(3) . ?
C3 C4 1.501(4) . ?
C3 C2 1.550(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.351(4) . ?
C4 C5 1.430(3) . ?
C6 C12 1.379(4) . ?
C2 C1 1.509(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(5) . ?
C12 H12 0.9300 . ?
C12 C11 1.377(5) . ?
C11 H11 0.9300 . ?

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
C5 O2 C6 121.91(18) . . ?
H1A N1 H1B 120.0 . . ?
C8 N1 H1A 120.0 . . ?
C8 N1 H1B 120.0 . . ?
N1 C8 C7 117.62(19) . . ?
N1 C8 C4 124.0(2) . . ?
C4 C8 C7 118.36(19) . . ?
C9 C7 C8 123.7(2) . . ?
C6 C7 C8 118.9(2) . . ?
C6 C7 C9 117.4(2) . . ?
F7 C3 C4 110.6(2) . . ?
F7 C3 C2 102.9(2) . . ?
F6 C3 F7 104.6(2) . . ?
F6 C3 C4 112.7(2) . . ?
F6 C3 C2 106.5(2) . . ?
C4 C3 C2 118.3(2) . . ?
C7 C9 H9 119.4 . . ?
C10 C9 C7 121.2(3) . . ?
C10 C9 H9 119.4 . . ?
C8 C4 C3 123.2(2) . . ?
C8 C4 C5 120.6(2) . . ?
C5 C4 C3 116.2(2) . . ?
O2 C5 C4 118.8(2) . . ?
O1 C5 O2 115.4(2) . . ?
O1 C5 C4 125.9(3) . . ?
O2 C6 C7 121.2(2) . . ?
O2 C6 C12 116.7(2) . . ?
C12 C6 C7 122.1(3) . . ?
F5 C2 F4 108.5(2) . . ?
F5 C2 C3 107.2(2) . . ?
F5 C2 C1 106.4(3) . . ?
F4 C2 C3 109.4(3) . . ?
F4 C2 C1 105.3(2) . . ?
C1 C2 C3 119.7(2) . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.1(3) . . ?
C11 C10 H10 120.0 . . ?
F1 C1 F3 107.6(3) . . ?
F1 C1 F2 108.9(3) . . ?
F1 C1 C2 111.8(3) . . ?
F3 C1 C2 108.8(3) . . ?
F2 C1 F3 108.9(3) . . ?
F2 C1 C2 110.7(3) . . ?
C6 C12 H12 120.7 . . ?
C11 C12 C6 118.6(3) . . ?
C11 C12 H12 120.7 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.6 . . ?

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
F7 C3 C4 C8 29.9(3) . . . . ?
F7 C3 C4 C5 -151.5(2) . . . . ?
F7 C3 C2 F5 -64.0(3) . . . . ?
F7 C3 C2 F4 53.4(3) . . . . ?
F7 C3 C2 C1 174.9(2) . . . . ?
F5 C2 C1 F1 179.1(2) . . . . ?
F5 C2 C1 F3 60.4(3) . . . . ?
F5 C2 C1 F2 -59.3(3) . . . . ?
F6 C3 C4 C8 146.7(2) . . . . ?
F6 C3 C4 C5 -34.8(3) . . . . ?
F6 C3 C2 F5 -173.8(2) . . . . ?
F6 C3 C2 F4 -56.3(3) . . . . ?
F6 C3 C2 C1 65.1(3) . . . . ?
F4 C2 C1 F1 64.0(3) . . . . ?
F4 C2 C1 F3 -54.7(3) . . . . ?
F4 C2 C1 F2 -174.4(2) . . . . ?
O2 C6 C12 C11 -178.8(3) . . . . ?
N1 C8 C7 C9 -2.3(3) . . . . ?
N1 C8 C7 C6 178.6(2) . . . . ?
N1 C8 C4 C3 3.9(4) . . . . ?
N1 C8 C4 C5 -174.6(2) . . . . ?
C8 C7 C9 C10 -179.0(2) . . . . ?
C8 C7 C6 O2 -2.1(3) . . . . ?
C8 C7 C6 C12 179.3(2) . . . . ?
C8 C4 C5 O2 -5.9(4) . . . . ?
C8 C4 C5 O1 173.4(3) . . . . ?
C7 C8 C4 C3 -176.7(2) . . . . ?
C7 C8 C4 C5 4.9(3) . . . . ?
C7 C9 C10 C11 -0.2(4) . . . . ?
C7 C6 C12 C11 -0.2(4) . . . . ?
C3 C4 C5 O2 175.5(2) . . . . ?
C3 C4 C5 O1 -5.2(4) . . . . ?
C3 C2 C1 F1 -59.5(4) . . . . ?
C3 C2 C1 F3 -178.2(3) . . . . ?
C3 C2 C1 F2 62.2(4) . . . . ?
C9 C7 C6 O2 178.6(2) . . . . ?
C9 C7 C6 C12 0.0(4) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C4 C8 C7 C9 178.3(2) . . . . ?
C4 C8 C7 C6 -0.9(3) . . . . ?
C4 C3 C2 F5 58.2(3) . . . . ?
C4 C3 C2 F4 175.63(19) . . . . ?
C4 C3 C2 C1 -62.9(3) . . . . ?
C5 O2 C6 C7 1.1(4) . . . . ?
C5 O2 C6 C12 179.8(3) . . . . ?
C6 O2 C5 O1 -176.5(3) . . . . ?
C6 O2 C5 C4 2.9(4) . . . . ?
C6 C7 C9 C10 0.1(4) . . . . ?
C6 C12 C11 C10 0.1(5) . . . . ?
C2 C3 C4 C8 -88.3(3) . . . . ?
C2 C3 C4 C5 90.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
