# Supplementary Information (SI) for ChemComm.
# 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_240305_nwj_2
_database_code_depnum_ccdc_archive 'CCDC 2373144'
loop_
_audit_author_name
_audit_author_address
MLQ-O
;university of south china
China
;
_audit_update_record             
;
2024-07-24 deposited with the CCDC.	2024-10-01 downloaded from the CCDC.
;
_audit_creation_date             2024-03-06
_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         'C11 H6 F3 N3 O'
_chemical_formula_sum            'C11 H6 F3 N3 O'
_chemical_formula_weight         253.19
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.0758(5)
_cell_length_b                   12.1758(6)
_cell_length_c                   6.8549(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.473(2)
_cell_angle_gamma                90
_cell_volume                     999.33(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7855
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.431
_cell_measurement_theta_min      4.506
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    0.844
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1198 before and 0.0524 after correction.
The Ratio of minimum to maximum transmission is 0.8828.
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    1.683
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11560
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.702
_diffrn_reflns_theta_min         4.506
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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             0.24957869999999996
_diffrn_source_voltage           69.91
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2031
_reflns_number_total             2284
_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 (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_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         0.300
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.102
_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)+(0.0540P)²+0.3213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1040
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5)
;
_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 0.09496(7) 0.64676(8) 0.40539(15) 0.0470(3) Uani 1 1 d . . . . .
O1 O 0.38407(7) 0.46123(7) 0.67999(13) 0.0238(2) Uani 1 1 d . . . . .
N1 N 0.50174(8) 0.46293(9) 0.74340(16) 0.0228(2) Uani 1 1 d . . . . .
C1 C 0.67321(11) 0.70100(10) 0.91993(18) 0.0247(3) Uani 1 1 d . . . . .
H1 H 0.614465 0.753034 0.918171 0.030 Uiso 1 1 calc R U . . .
F2 F 0.12631(7) 0.49592(7) 0.56422(15) 0.0398(2) Uani 1 1 d . . . . .
N2 N 0.39824(9) 0.74039(8) 0.71953(16) 0.0232(2) Uani 1 1 d . . . . .
H2 H 0.438557 0.800025 0.746063 0.028 Uiso 1 1 calc R U . . .
C2 C 0.78109(12) 0.73071(11) 0.99368(19) 0.0285(3) Uani 1 1 d . . . . .
H2A H 0.796275 0.802886 1.042617 0.034 Uiso 1 1 calc R U . . .
F3 F 0.07186(7) 0.63824(8) 0.70881(16) 0.0469(3) Uani 1 1 d . . . . .
N3 N 0.28704(9) 0.73945(9) 0.66200(17) 0.0253(2) Uani 1 1 d . . . . .
C3 C 0.86708(12) 0.65507(12) 0.9962(2) 0.0315(3) Uani 1 1 d . . . . .
H3 H 0.941211 0.675196 1.047218 0.038 Uiso 1 1 calc R U . . .
C4 C 0.84450(11) 0.54974(12) 0.9237(2) 0.0328(3) Uani 1 1 d . . . . .
H4 H 0.903505 0.498027 0.925089 0.039 Uiso 1 1 calc R U . . .
C5 C 0.73661(11) 0.51957(11) 0.8496(2) 0.0274(3) Uani 1 1 d . . . . .
H5 H 0.721779 0.447482 0.799923 0.033 Uiso 1 1 calc R U . . .
C6 C 0.65003(10) 0.59503(10) 0.84801(17) 0.0206(3) Uani 1 1 d . . . . .
C7 C 0.53421(10) 0.56595(10) 0.77421(17) 0.0204(2) Uani 1 1 d . . . . .
C8 C 0.43937(10) 0.63588(10) 0.73080(17) 0.0204(3) Uani 1 1 d . . . . .
C9 C 0.35113(10) 0.56740(10) 0.67704(18) 0.0214(3) Uani 1 1 d . . . . .
C10 C 0.25639(10) 0.63436(10) 0.63636(19) 0.0230(3) Uani 1 1 d . . . . .
C11 C 0.13703(11) 0.60466(11) 0.5787(2) 0.0274(3) 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 C11 1.3324(16) . ?
O1 N1 1.4310(13) . ?
O1 C9 1.3519(14) . ?
N1 C7 1.3229(16) . ?
C1 H1 0.9500 . ?
C1 C2 1.3829(18) . ?
C1 C6 1.3965(17) . ?
F2 C11 1.3327(15) . ?
N2 H2 0.8800 . ?
N2 N3 1.3494(15) . ?
N2 C8 1.3645(15) . ?
C2 H2A 0.9500 . ?
C2 C3 1.386(2) . ?
F3 C11 1.3284(16) . ?
N3 C10 1.3372(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3851(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3909(18) . ?
C6 C7 1.4674(16) . ?
C7 C8 1.4271(16) . ?
C8 C9 1.3654(17) . ?
C9 C10 1.4030(17) . ?
C10 C11 1.4888(17) . ?

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
C9 O1 N1 105.62(8) . . ?
C7 N1 O1 108.92(9) . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.45(12) . . ?
C6 C1 H1 119.8 . . ?
N3 N2 H2 124.8 . . ?
N3 N2 C8 110.47(10) . . ?
C8 N2 H2 124.8 . . ?
C1 C2 H2A 120.0 . . ?
C1 C2 C3 119.95(12) . . ?
C3 C2 H2A 120.0 . . ?
C10 N3 N2 107.12(10) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.80(13) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.49(13) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.86(12) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C7 118.88(11) . . ?
C5 C6 C1 119.45(11) . . ?
C5 C6 C7 121.67(11) . . ?
N1 C7 C6 122.23(11) . . ?
N1 C7 C8 108.62(10) . . ?
C8 C7 C6 129.12(11) . . ?
N2 C8 C7 147.63(11) . . ?
N2 C8 C9 106.77(10) . . ?
C9 C8 C7 105.60(11) . . ?
O1 C9 C8 111.23(10) . . ?
O1 C9 C10 142.12(11) . . ?
C8 C9 C10 106.64(11) . . ?
N3 C10 C9 108.98(11) . . ?
N3 C10 C11 120.61(11) . . ?
C9 C10 C11 130.38(12) . . ?
F1 C11 F2 107.08(11) . . ?
F1 C11 C10 112.77(11) . . ?
F2 C11 C10 110.02(10) . . ?
F3 C11 F1 106.84(11) . . ?
F3 C11 F2 107.19(11) . . ?
F3 C11 C10 112.62(11) . . ?

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
O1 N1 C7 C6 177.57(10) . . . . ?
O1 N1 C7 C8 -0.44(13) . . . . ?
O1 C9 C10 N3 -178.59(15) . . . . ?
O1 C9 C10 C11 3.1(3) . . . . ?
N1 O1 C9 C8 0.94(13) . . . . ?
N1 O1 C9 C10 -179.60(16) . . . . ?
N1 C7 C8 N2 -179.08(18) . . . . ?
N1 C7 C8 C9 0.99(13) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C1 C6 C7 N1 -165.28(11) . . . . ?
C1 C6 C7 C8 12.29(19) . . . . ?
N2 N3 C10 C9 -0.59(14) . . . . ?
N2 N3 C10 C11 177.95(11) . . . . ?
N2 C8 C9 O1 178.84(10) . . . . ?
N2 C8 C9 C10 -0.81(13) . . . . ?
C2 C1 C6 C5 -0.52(19) . . . . ?
C2 C1 C6 C7 178.91(11) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
N3 N2 C8 C7 -179.44(17) . . . . ?
N3 N2 C8 C9 0.48(14) . . . . ?
N3 C10 C11 F1 61.30(16) . . . . ?
N3 C10 C11 F2 -179.22(12) . . . . ?
N3 C10 C11 F3 -59.72(17) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C4 C5 C6 C7 -178.86(12) . . . . ?
C5 C6 C7 N1 14.13(18) . . . . ?
C5 C6 C7 C8 -168.31(12) . . . . ?
C6 C1 C2 C3 0.1(2) . . . . ?
C6 C7 C8 N2 3.1(3) . . . . ?
C6 C7 C8 C9 -176.83(12) . . . . ?
C7 C8 C9 O1 -1.20(13) . . . . ?
C7 C8 C9 C10 179.15(10) . . . . ?
C8 N2 N3 C10 0.07(14) . . . . ?
C8 C9 C10 N3 0.88(14) . . . . ?
C8 C9 C10 C11 -177.46(13) . . . . ?
C9 O1 N1 C7 -0.28(13) . . . . ?
C9 C10 C11 F1 -120.51(15) . . . . ?
C9 C10 C11 F2 -1.04(19) . . . . ?
C9 C10 C11 F3 118.47(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_240707_mlq_2_93_0m
_database_code_depnum_ccdc_archive 'CCDC 2373147'
loop_
_audit_author_name
_audit_author_address
MLQ-Three
;university of south china
China
;
_audit_update_record             
;
2024-07-24 deposited with the CCDC.	2024-10-01 downloaded from the CCDC.
;
_audit_creation_date             2024-07-09
_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         'H2 O, 2(C10 H5 F3 N4)'
_chemical_formula_sum            'C20 H12 F6 N8 O'
_chemical_formula_weight         494.38
_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      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                   7.5837(6)
_cell_length_b                   8.1452(7)
_cell_length_c                   16.1468(13)
_cell_angle_alpha                95.204(3)
_cell_angle_beta                 93.854(3)
_cell_angle_gamma                90.608(4)
_cell_volume                     990.90(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6112
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.700
_cell_measurement_theta_min      4.744
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.892
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0968 before and 0.0598 after correction.
The Ratio of minimum to maximum transmission is 0.8518.
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    1.657
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13566
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         56.962
_diffrn_reflns_theta_min         4.743
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  '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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3267
_reflns_number_total             3971
_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 (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_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         0.264
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         3971
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.073
_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)+(0.0510P)²+0.1139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1049
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), N4(H4), C5(H5), C6(H6), N8(H8), C11(H11), C12(H12), C15(H15),
 C16(H16)
;
_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
O1 O 0.36775(14) 0.23430(13) 0.54645(6) 0.0320(3) Uani 1 1 d G . . . .
H1A H 0.349600 0.339150 0.557161 0.048 Uiso 1 1 d G U . . .
H1B H 0.271886 0.186497 0.559817 0.048 Uiso 1 1 d G U . . .
F1 F 0.76660(12) 0.31437(11) 0.94113(5) 0.0393(2) Uani 1 1 d . . . . .
N1 N 0.79593(16) -0.07535(15) 0.92198(7) 0.0258(3) Uani 1 1 d . . . . .
C1 C 0.9210(2) -0.34255(19) 0.90464(9) 0.0306(3) Uani 1 1 d . . . . .
H1 H 0.980093 -0.427943 0.931138 0.037 Uiso 1 1 calc R U . . .
F2 F 0.51411(12) 0.20468(11) 0.95518(5) 0.0380(2) Uani 1 1 d . . . . .
N2 N 0.88439(16) -0.36340(15) 0.82324(8) 0.0287(3) Uani 1 1 d . . . . .
C2 C 0.8767(2) -0.20028(19) 0.95371(9) 0.0293(3) Uani 1 1 d . . . . .
H2 H 0.905872 -0.193526 1.012072 0.035 Uiso 1 1 calc R U . . .
F3 F 0.52987(15) 0.43318(11) 0.89898(6) 0.0467(3) Uani 1 1 d . . . . .
N3 N 0.54242(16) 0.26474(15) 0.75312(7) 0.0279(3) Uani 1 1 d . . . . .
C3 C 0.75980(17) -0.09211(17) 0.83823(8) 0.0216(3) Uani 1 1 d . . . . .
N4 N 0.56463(16) 0.15463(15) 0.68700(7) 0.0277(3) Uani 1 1 d . . . . .
H4 H 0.532265 0.171523 0.635136 0.033 Uiso 1 1 calc R U . . .
C4 C 0.80239(18) -0.23659(17) 0.78830(8) 0.0241(3) Uani 1 1 d . . . . .
C5 C 0.76202(19) -0.25259(18) 0.69965(9) 0.0280(3) Uani 1 1 d . . . . .
H5 H 0.790635 -0.351742 0.668123 0.034 Uiso 1 1 calc R U . . .
C6 C 0.68440(19) -0.13027(18) 0.65996(8) 0.0279(3) Uani 1 1 d . . . . .
H6 H 0.658936 -0.141059 0.601288 0.034 Uiso 1 1 calc R U . . .
C7 C 0.64244(18) 0.01539(18) 0.70982(8) 0.0246(3) Uani 1 1 d . . . . .
C8 C 0.67581(18) 0.03665(17) 0.79641(8) 0.0225(3) Uani 1 1 d . . . . .
C9 C 0.61000(18) 0.19461(17) 0.81918(8) 0.0239(3) Uani 1 1 d . . . . .
C10 C 0.6044(2) 0.28630(18) 0.90342(9) 0.0292(3) Uani 1 1 d . . . . .
F4 F 0.26221(14) -0.12643(12) 0.50585(5) 0.0423(3) Uani 1 1 d . . . . .
F5 F 0.22814(15) -0.38620(12) 0.47430(6) 0.0497(3) Uani 1 1 d . . . . .
N5 N 0.11188(16) 0.06687(15) 0.66040(7) 0.0276(3) Uani 1 1 d . . . . .
F6 F 0.01451(13) -0.24349(15) 0.52203(6) 0.0517(3) Uani 1 1 d . . . . .
N6 N 0.13120(17) 0.16790(15) 0.83291(7) 0.0284(3) Uani 1 1 d . . . . .
N7 N 0.32324(17) -0.43879(15) 0.62935(7) 0.0290(3) Uani 1 1 d . . . . .
N8 N 0.36031(16) -0.43455(14) 0.71229(7) 0.0272(3) Uani 1 1 d . . . . .
H8 H 0.409499 -0.515929 0.737244 0.033 Uiso 1 1 calc R U . . .
C11 C 0.0638(2) 0.26155(19) 0.77670(9) 0.0301(3) Uani 1 1 d . . . . .
H11 H 0.019855 0.366594 0.794783 0.036 Uiso 1 1 calc R U . . .
C12 C 0.0549(2) 0.21129(19) 0.69112(9) 0.0300(3) Uani 1 1 d . . . . .
H12 H 0.005729 0.284313 0.653457 0.036 Uiso 1 1 calc R U . . .
C13 C 0.17844(18) -0.03281(17) 0.71708(8) 0.0228(3) Uani 1 1 d . . . . .
C14 C 0.19036(18) 0.01822(17) 0.80394(8) 0.0239(3) Uani 1 1 d . . . . .
C15 C 0.26619(19) -0.08655(18) 0.86344(8) 0.0263(3) Uani 1 1 d . . . . .
H15 H 0.272888 -0.048971 0.921025 0.032 Uiso 1 1 calc R U . . .
C16 C 0.32831(19) -0.23750(17) 0.83943(8) 0.0264(3) Uani 1 1 d . . . . .
H16 H 0.380088 -0.305433 0.878944 0.032 Uiso 1 1 calc R U . . .
C17 C 0.31309(18) -0.29047(17) 0.75282(8) 0.0236(3) Uani 1 1 d . . . . .
C18 C 0.24065(18) -0.19339(17) 0.69232(8) 0.0234(3) Uani 1 1 d . . . . .
C19 C 0.25118(19) -0.29496(17) 0.61641(8) 0.0253(3) Uani 1 1 d . . . . .
C20 C 0.1896(2) -0.26263(19) 0.52991(9) 0.0322(4) 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
O1 H1A 0.8701 . ?
O1 H1B 0.8701 . ?
F1 C10 1.3434(17) . ?
N1 C2 1.3185(19) . ?
N1 C3 1.3559(17) . ?
C1 H1 0.9500 . ?
C1 N2 1.3203(19) . ?
C1 C2 1.400(2) . ?
F2 C10 1.3329(18) . ?
N2 C4 1.3579(19) . ?
C2 H2 0.9500 . ?
F3 C10 1.3342(17) . ?
N3 N4 1.3514(17) . ?
N3 C9 1.3304(18) . ?
C3 C4 1.4177(19) . ?
C3 C8 1.431(2) . ?
N4 H4 0.8800 . ?
N4 C7 1.3532(19) . ?
C4 C5 1.4374(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.352(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.423(2) . ?
C7 C8 1.3987(19) . ?
C8 C9 1.411(2) . ?
C9 C10 1.495(2) . ?
F4 C20 1.3338(19) . ?
F5 C20 1.3352(17) . ?
N5 C12 1.3229(19) . ?
N5 C13 1.3540(18) . ?
F6 C20 1.3372(19) . ?
N6 C11 1.318(2) . ?
N6 C14 1.3575(19) . ?
N7 N8 1.3471(17) . ?
N7 C19 1.3257(19) . ?
N8 H8 0.8800 . ?
N8 C17 1.3546(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.402(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.4227(19) . ?
C13 C18 1.427(2) . ?
C14 C15 1.438(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.354(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.4222(19) . ?
C17 C18 1.3995(19) . ?
C18 C19 1.4227(19) . ?
C19 C20 1.490(2) . ?

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
H1A O1 H1B 104.5 . . ?
C2 N1 C3 115.76(12) . . ?
N2 C1 H1 118.5 . . ?
N2 C1 C2 122.99(14) . . ?
C2 C1 H1 118.5 . . ?
C1 N2 C4 116.13(12) . . ?
N1 C2 C1 122.50(13) . . ?
N1 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
C9 N3 N4 105.42(12) . . ?
N1 C3 C4 122.03(13) . . ?
N1 C3 C8 120.91(12) . . ?
C4 C3 C8 117.05(12) . . ?
N3 N4 H4 123.9 . . ?
N3 N4 C7 112.13(11) . . ?
C7 N4 H4 123.9 . . ?
N2 C4 C3 120.57(12) . . ?
N2 C4 C5 118.18(12) . . ?
C3 C4 C5 121.25(13) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.74(13) . . ?
C6 C5 H5 119.1 . . ?
C5 C6 H6 121.4 . . ?
C5 C6 C7 117.17(13) . . ?
C7 C6 H6 121.4 . . ?
N4 C7 C6 129.64(12) . . ?
N4 C7 C8 106.78(12) . . ?
C8 C7 C6 123.57(13) . . ?
C7 C8 C3 119.21(12) . . ?
C7 C8 C9 104.06(12) . . ?
C9 C8 C3 136.73(12) . . ?
N3 C9 C8 111.59(12) . . ?
N3 C9 C10 118.62(13) . . ?
C8 C9 C10 129.79(13) . . ?
F1 C10 C9 112.13(12) . . ?
F2 C10 F1 106.11(11) . . ?
F2 C10 F3 107.36(12) . . ?
F2 C10 C9 112.58(12) . . ?
F3 C10 F1 106.70(12) . . ?
F3 C10 C9 111.59(12) . . ?
C12 N5 C13 115.83(12) . . ?
C11 N6 C14 116.60(12) . . ?
C19 N7 N8 105.75(11) . . ?
N7 N8 H8 123.9 . . ?
N7 N8 C17 112.16(11) . . ?
C17 N8 H8 123.9 . . ?
N6 C11 H11 118.9 . . ?
N6 C11 C12 122.21(14) . . ?
C12 C11 H11 118.9 . . ?
N5 C12 C11 123.02(14) . . ?
N5 C12 H12 118.5 . . ?
C11 C12 H12 118.5 . . ?
N5 C13 C14 121.48(13) . . ?
N5 C13 C18 121.47(12) . . ?
C14 C13 C18 117.04(12) . . ?
N6 C14 C13 120.83(13) . . ?
N6 C14 C15 118.11(12) . . ?
C13 C14 C15 121.06(13) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.63(13) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 H16 121.3 . . ?
C15 C16 C17 117.49(13) . . ?
C17 C16 H16 121.3 . . ?
N8 C17 C16 129.85(13) . . ?
N8 C17 C18 106.96(12) . . ?
C18 C17 C16 123.19(13) . . ?
C17 C18 C13 119.56(12) . . ?
C17 C18 C19 103.61(12) . . ?
C19 C18 C13 136.83(13) . . ?
N7 C19 C18 111.52(12) . . ?
N7 C19 C20 119.03(12) . . ?
C18 C19 C20 129.42(13) . . ?
F4 C20 F5 106.59(12) . . ?
F4 C20 F6 106.48(13) . . ?
F4 C20 C19 112.81(12) . . ?
F5 C20 F6 107.01(12) . . ?
F5 C20 C19 111.83(13) . . ?
F6 C20 C19 111.73(13) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_240707_mlq_2_60_0m
_database_code_depnum_ccdc_archive 'CCDC 2373145'
loop_
_audit_author_name
_audit_author_address
MLQ-Two
;university of south china
China
;
_audit_update_record             
;
2024-07-24 deposited with the CCDC.	2024-10-01 downloaded from the CCDC.
;
_audit_creation_date             2024-07-09
_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 H7 Cl F3 N3 O2'
_chemical_formula_sum            'C12 H7 Cl F3 N3 O2'
_chemical_formula_weight         317.66
_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'
Cl Cl 0.3281 0.5435 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.0457(6)
_cell_length_b                   23.6493(19)
_cell_length_c                   30.637(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5104.9(7)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9811
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      58.583
_cell_measurement_theta_min      3.252
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.777
_exptl_absorpt_coefficient_mu    2.044
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1129 before and 0.0631 after correction.
The Ratio of minimum to maximum transmission is 0.7961.
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    1.653
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2560
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            61073
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.679
_diffrn_reflns_theta_min         3.252
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  '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             0.24957869999999996
_diffrn_source_voltage           69.91
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4496
_reflns_number_total             5844
_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 (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_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         0.274
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5844
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²+2.6488P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1156
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), N2(H2), C3(H3), C4(H4), N5(H5), C13(H13), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C23(H23A,H23B,H23C)
;
_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
Cl1 Cl 0.19667(8) 0.39000(2) 0.37849(2) 0.04909(15) Uani 1 1 d . . . . .
F1 F 0.3493(2) 0.77948(5) 0.55480(5) 0.0676(4) Uani 1 1 d . . . . .
O1 O 0.21585(19) 0.49229(5) 0.55304(4) 0.0354(3) Uani 1 1 d . . . . .
N1 N 0.3681(2) 0.58767(6) 0.44606(5) 0.0375(4) Uani 1 1 d . . . . .
C1 C 0.2625(3) 0.47492(8) 0.43562(6) 0.0331(4) Uani 1 1 d . . . . .
H1 H 0.299995 0.496516 0.410934 0.040 Uiso 1 1 calc R U . . .
F2 F 0.5167(2) 0.76194(5) 0.49860(5) 0.0643(4) Uani 1 1 d . . . . .
O2 O 0.4151(2) 0.64419(5) 0.45810(4) 0.0391(3) Uani 1 1 d . . . . .
N2 N 0.3170(2) 0.60379(6) 0.56208(5) 0.0330(3) Uani 1 1 d . . . . .
H2 H 0.280840 0.577290 0.580451 0.040 Uiso 1 1 calc R U . . .
C2 C 0.2052(3) 0.41933(8) 0.43035(6) 0.0351(4) Uani 1 1 d . . . . .
F3 F 0.6327(2) 0.74993(6) 0.56181(6) 0.0800(5) Uani 1 1 d . . . . .
N3 N 0.3612(2) 0.65713(6) 0.57378(5) 0.0353(4) Uani 1 1 d . . . . .
C3 C 0.1542(3) 0.38690(8) 0.46589(7) 0.0363(4) Uani 1 1 d . . . . .
H3 H 0.116243 0.348691 0.461965 0.044 Uiso 1 1 calc R U . . .
C4 C 0.1585(3) 0.41031(8) 0.50733(6) 0.0341(4) Uani 1 1 d . . . . .
H4 H 0.124785 0.387893 0.531872 0.041 Uiso 1 1 calc R U . . .
C5 C 0.2119(2) 0.46643(7) 0.51325(6) 0.0297(4) Uani 1 1 d . . . . .
C6 C 0.2653(2) 0.49931(7) 0.47709(6) 0.0297(4) Uani 1 1 d . . . . .
C7 C 0.3213(2) 0.55910(7) 0.48171(6) 0.0297(4) Uani 1 1 d . . . . .
C8 C 0.3353(2) 0.59614(7) 0.51843(6) 0.0291(4) Uani 1 1 d . . . . .
C9 C 0.3930(2) 0.64684(7) 0.50172(6) 0.0310(4) Uani 1 1 d . . . . .
C10 C 0.4085(3) 0.68431(7) 0.53706(6) 0.0329(4) Uani 1 1 d . . . . .
C11 C 0.1618(3) 0.45934(8) 0.59045(6) 0.0409(5) Uani 1 1 d . . . . .
H11A H 0.035844 0.442935 0.585590 0.061 Uiso 1 1 calc R U . . .
H11B H 0.158439 0.483661 0.616336 0.061 Uiso 1 1 calc R U . . .
H11C H 0.254323 0.428940 0.594934 0.061 Uiso 1 1 calc R U . . .
C12 C 0.4754(3) 0.74363(8) 0.53860(7) 0.0411(5) Uani 1 1 d . . . . .
Cl2 Cl 0.01407(9) 0.84178(2) 0.84424(2) 0.05834(17) Uani 1 1 d . . . . .
O3 O 0.1045(2) 0.73756(5) 0.67153(5) 0.0403(3) Uani 1 1 d . . . . .
F4 F 0.5418(2) 0.48029(6) 0.66430(5) 0.0701(5) Uani 1 1 d . . . . .
O4 O 0.2883(2) 0.59015(5) 0.77234(4) 0.0376(3) Uani 1 1 d . . . . .
N4 N 0.2214(2) 0.64557(6) 0.78234(5) 0.0366(4) Uani 1 1 d . . . . .
F5 F 0.2865(2) 0.45380(5) 0.69475(5) 0.0539(3) Uani 1 1 d . . . . .
N5 N 0.2637(2) 0.63052(6) 0.66633(5) 0.0364(4) Uani 1 1 d . . . . .
H5 H 0.237705 0.656692 0.646810 0.044 Uiso 1 1 calc R U . . .
F6 F 0.5147(2) 0.48375(5) 0.73419(5) 0.0666(4) Uani 1 1 d . . . . .
N6 N 0.3295(3) 0.57811(6) 0.65656(5) 0.0388(4) Uani 1 1 d . . . . .
C13 C 0.1002(3) 0.75647(8) 0.78923(7) 0.0347(4) Uani 1 1 d . . . . .
H13 H 0.126462 0.735101 0.814786 0.042 Uiso 1 1 calc R U . . .
C14 C 0.0375(3) 0.81168(8) 0.79263(7) 0.0391(4) Uani 1 1 d . . . . .
C15 C -0.0015(3) 0.84351(8) 0.75606(8) 0.0405(5) Uani 1 1 d . . . . .
H15 H -0.043342 0.881511 0.758973 0.049 Uiso 1 1 calc R U . . .
C16 C 0.0207(3) 0.81994(8) 0.71521(7) 0.0393(5) Uani 1 1 d . . . . .
H16 H -0.006139 0.841786 0.689927 0.047 Uiso 1 1 calc R U . . .
C17 C 0.0822(3) 0.76415(8) 0.71084(6) 0.0338(4) Uani 1 1 d . . . . .
C18 C 0.1246(2) 0.73232(7) 0.74812(6) 0.0306(4) Uani 1 1 d . . . . .
C19 C 0.1942(2) 0.67347(7) 0.74547(6) 0.0300(4) Uani 1 1 d . . . . .
C20 C 0.2431(2) 0.63740(7) 0.70977(6) 0.0298(4) Uani 1 1 d . . . . .
C21 C 0.2976(3) 0.58777(7) 0.72830(6) 0.0311(4) Uani 1 1 d . . . . .
C22 C 0.3513(3) 0.55131(7) 0.69467(6) 0.0330(4) Uani 1 1 d . . . . .
C23 C 0.0380(3) 0.76615(10) 0.63303(7) 0.0487(5) Uani 1 1 d . . . . .
H23A H 0.048858 0.740829 0.607829 0.073 Uiso 1 1 calc R U . . .
H23B H 0.114822 0.800071 0.628009 0.073 Uiso 1 1 calc R U . . .
H23C H -0.095126 0.777028 0.637006 0.073 Uiso 1 1 calc R U . . .
C24 C 0.4246(3) 0.49253(8) 0.69669(7) 0.0401(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
Cl1 C2 1.7346(19) . ?
F1 C12 1.324(2) . ?
O1 C5 1.364(2) . ?
O1 C11 1.437(2) . ?
N1 O2 1.426(2) . ?
N1 C7 1.326(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(3) . ?
C1 C6 1.396(3) . ?
F2 C12 1.332(3) . ?
O2 C9 1.347(2) . ?
N2 H2 0.8800 . ?
N2 N3 1.348(2) . ?
N2 C8 1.356(2) . ?
C2 C3 1.379(3) . ?
F3 C12 1.325(3) . ?
N3 C10 1.338(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(3) . ?
C5 C6 1.405(2) . ?
C6 C7 1.475(2) . ?
C7 C8 1.429(3) . ?
C8 C9 1.365(2) . ?
C9 C10 1.403(3) . ?
C10 C12 1.481(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
Cl2 C14 1.742(2) . ?
O3 C17 1.368(2) . ?
O3 C23 1.438(2) . ?
F4 C24 1.323(2) . ?
O4 N4 1.4258(19) . ?
O4 C21 1.352(2) . ?
N4 C19 1.322(2) . ?
F5 C24 1.338(2) . ?
N5 H5 0.8800 . ?
N5 N6 1.357(2) . ?
N5 C20 1.349(2) . ?
F6 C24 1.329(2) . ?
N6 C22 1.337(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(3) . ?
C13 C18 1.394(3) . ?
C14 C15 1.377(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.379(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.395(3) . ?
C17 C18 1.400(3) . ?
C18 C19 1.478(2) . ?
C19 C20 1.429(3) . ?
C20 C21 1.359(2) . ?
C21 C22 1.396(3) . ?
C22 C24 1.484(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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 O1 C11 117.64(14) . . ?
C7 N1 O2 108.80(14) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C6 120.17(18) . . ?
C6 C1 H1 119.9 . . ?
C9 O2 N1 105.86(13) . . ?
N3 N2 H2 124.3 . . ?
N3 N2 C8 111.42(14) . . ?
C8 N2 H2 124.3 . . ?
C1 C2 Cl1 119.77(15) . . ?
C3 C2 Cl1 119.45(15) . . ?
C3 C2 C1 120.78(18) . . ?
C10 N3 N2 106.48(15) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.71(17) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.42(18) . . ?
C5 C4 H4 119.8 . . ?
O1 C5 C4 123.34(16) . . ?
O1 C5 C6 116.81(15) . . ?
C4 C5 C6 119.85(17) . . ?
C1 C6 C5 119.04(16) . . ?
C1 C6 C7 119.17(16) . . ?
C5 C6 C7 121.78(16) . . ?
N1 C7 C6 118.42(16) . . ?
N1 C7 C8 108.60(15) . . ?
C8 C7 C6 132.98(16) . . ?
N2 C8 C7 148.39(16) . . ?
N2 C8 C9 106.32(16) . . ?
C9 C8 C7 105.29(16) . . ?
O2 C9 C8 111.45(16) . . ?
O2 C9 C10 141.79(16) . . ?
C8 C9 C10 106.76(16) . . ?
N3 C10 C9 109.02(15) . . ?
N3 C10 C12 120.51(17) . . ?
C9 C10 C12 130.37(17) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
F1 C12 F2 106.45(17) . . ?
F1 C12 F3 106.73(19) . . ?
F1 C12 C10 113.90(17) . . ?
F2 C12 C10 110.37(17) . . ?
F3 C12 F2 105.92(18) . . ?
F3 C12 C10 112.95(17) . . ?
C17 O3 C23 117.96(15) . . ?
C21 O4 N4 105.58(13) . . ?
C19 N4 O4 108.86(14) . . ?
N6 N5 H5 124.3 . . ?
C20 N5 H5 124.3 . . ?
C20 N5 N6 111.39(14) . . ?
C22 N6 N5 106.24(15) . . ?
C14 C13 H13 120.2 . . ?
C14 C13 C18 119.65(18) . . ?
C18 C13 H13 120.2 . . ?
C13 C14 Cl2 118.98(17) . . ?
C15 C14 Cl2 119.74(15) . . ?
C15 C14 C13 121.25(19) . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.65(18) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.30(19) . . ?
C17 C16 H16 119.9 . . ?
O3 C17 C16 123.70(18) . . ?
O3 C17 C18 116.53(15) . . ?
C16 C17 C18 119.77(18) . . ?
C13 C18 C17 119.37(16) . . ?
C13 C18 C19 118.46(17) . . ?
C17 C18 C19 122.17(17) . . ?
N4 C19 C18 118.12(16) . . ?
N4 C19 C20 108.71(15) . . ?
C20 C19 C18 133.16(17) . . ?
N5 C20 C19 148.56(17) . . ?
N5 C20 C21 106.11(16) . . ?
C21 C20 C19 105.30(16) . . ?
O4 C21 C20 111.54(16) . . ?
O4 C21 C22 140.84(17) . . ?
C20 C21 C22 107.57(16) . . ?
N6 C22 C21 108.68(16) . . ?
N6 C22 C24 121.36(17) . . ?
C21 C22 C24 129.96(17) . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
F4 C24 F5 105.71(17) . . ?
F4 C24 F6 108.44(19) . . ?
F4 C24 C22 113.02(16) . . ?
F5 C24 C22 112.72(17) . . ?
F6 C24 F5 106.18(16) . . ?
F6 C24 C22 110.40(16) . . ?

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
Cl1 C2 C3 C4 -179.21(14) . . . . ?
O1 C5 C6 C1 -179.61(15) . . . . ?
O1 C5 C6 C7 -0.5(2) . . . . ?
N1 O2 C9 C8 0.05(19) . . . . ?
N1 O2 C9 C10 -179.9(2) . . . . ?
N1 C7 C8 N2 179.5(3) . . . . ?
N1 C7 C8 C9 -0.2(2) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C1 C6 C7 N1 -0.2(2) . . . . ?
C1 C6 C7 C8 178.70(18) . . . . ?
O2 N1 C7 C6 179.46(14) . . . . ?
O2 N1 C7 C8 0.3(2) . . . . ?
O2 C9 C10 N3 179.8(2) . . . . ?
O2 C9 C10 C12 -3.9(4) . . . . ?
N2 N3 C10 C9 0.1(2) . . . . ?
N2 N3 C10 C12 -176.65(17) . . . . ?
N2 C8 C9 O2 -179.73(15) . . . . ?
N2 C8 C9 C10 0.3(2) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
C2 C1 C6 C7 -178.19(16) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
N3 N2 C8 C7 -179.9(3) . . . . ?
N3 N2 C8 C9 -0.2(2) . . . . ?
N3 C10 C12 F1 -61.1(3) . . . . ?
N3 C10 C12 F2 179.21(17) . . . . ?
N3 C10 C12 F3 60.8(3) . . . . ?
C3 C4 C5 O1 178.79(16) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C4 C5 C6 C7 179.47(16) . . . . ?
C5 C6 C7 N1 -179.31(16) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C6 C1 C2 Cl1 178.39(14) . . . . ?
C6 C1 C2 C3 -1.4(3) . . . . ?
C6 C7 C8 N2 0.5(4) . . . . ?
C6 C7 C8 C9 -179.26(18) . . . . ?
C7 N1 O2 C9 -0.21(19) . . . . ?
C7 C8 C9 O2 0.1(2) . . . . ?
C7 C8 C9 C10 -179.91(14) . . . . ?
C8 N2 N3 C10 0.1(2) . . . . ?
C8 C9 C10 N3 -0.2(2) . . . . ?
C8 C9 C10 C12 176.09(19) . . . . ?
C9 C10 C12 F1 122.9(2) . . . . ?
C9 C10 C12 F2 3.3(3) . . . . ?
C9 C10 C12 F3 -115.1(2) . . . . ?
C11 O1 C5 C4 0.0(2) . . . . ?
C11 O1 C5 C6 -179.97(16) . . . . ?
Cl2 C14 C15 C16 178.76(15) . . . . ?
O3 C17 C18 C13 -178.35(16) . . . . ?
O3 C17 C18 C19 1.4(2) . . . . ?
O4 N4 C19 C18 -179.93(14) . . . . ?
O4 N4 C19 C20 -0.3(2) . . . . ?
O4 C21 C22 N6 -177.4(2) . . . . ?
O4 C21 C22 C24 1.8(4) . . . . ?
N4 O4 C21 C20 0.4(2) . . . . ?
N4 O4 C21 C22 177.5(2) . . . . ?
N4 C19 C20 N5 -177.2(3) . . . . ?
N4 C19 C20 C21 0.5(2) . . . . ?
N5 N6 C22 C21 0.2(2) . . . . ?
N5 N6 C22 C24 -179.07(17) . . . . ?
N5 C20 C21 O4 178.20(15) . . . . ?
N5 C20 C21 C22 0.1(2) . . . . ?
N6 N5 C20 C19 177.7(3) . . . . ?
N6 N5 C20 C21 0.0(2) . . . . ?
N6 C22 C24 F4 29.7(3) . . . . ?
N6 C22 C24 F5 -90.1(2) . . . . ?
N6 C22 C24 F6 151.36(19) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C13 C18 C19 N4 3.1(2) . . . . ?
C13 C18 C19 C20 -176.40(18) . . . . ?
C14 C13 C18 C17 -1.0(3) . . . . ?
C14 C13 C18 C19 179.23(16) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 O3 178.87(17) . . . . ?
C15 C16 C17 C18 -1.0(3) . . . . ?
C16 C17 C18 C13 1.6(3) . . . . ?
C16 C17 C18 C19 -178.71(16) . . . . ?
C17 C18 C19 N4 -176.61(17) . . . . ?
C17 C18 C19 C20 3.9(3) . . . . ?
C18 C13 C14 Cl2 -178.24(14) . . . . ?
C18 C13 C14 C15 0.0(3) . . . . ?
C18 C19 C20 N5 2.3(4) . . . . ?
C18 C19 C20 C21 -179.91(18) . . . . ?
C19 C20 C21 O4 -0.6(2) . . . . ?
C19 C20 C21 C22 -178.67(15) . . . . ?
C20 N5 N6 C22 -0.1(2) . . . . ?
C20 C21 C22 N6 -0.2(2) . . . . ?
C20 C21 C22 C24 178.98(19) . . . . ?
C21 O4 N4 C19 -0.06(19) . . . . ?
C21 C22 C24 F4 -149.4(2) . . . . ?
C21 C22 C24 F5 90.9(2) . . . . ?
C21 C22 C24 F6 -27.7(3) . . . . ?
C23 O3 C17 C16 -8.2(3) . . . . ?
C23 O3 C17 C18 171.67(17) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
