# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_l_1
_database_code_depnum_ccdc_archive 'CCDC 2116196'
loop_
_audit_author_name
_audit_author_address
'Yong Zhang'
;GNNU
China
;
_audit_update_record             
;
2021-10-18 deposited with the CCDC.	2021-12-16 downloaded from the CCDC.
;
_audit_creation_date             2020-06-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H7 Cl2 F2 N3 O6'
_chemical_formula_sum            'C15 H7 Cl2 F2 N3 O6'
_chemical_formula_weight         434.14
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.4977(9)
_cell_length_b                   11.8470(8)
_cell_length_c                   12.9471(9)
_cell_angle_alpha                70.511(6)
_cell_angle_beta                 80.465(6)
_cell_angle_gamma                79.851(6)
_cell_volume                     1625.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3465
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      72.9020
_cell_measurement_theta_min      3.6060
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.225
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56918
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_av_unetI/netI     0.0893
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11200
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.723
_diffrn_reflns_theta_min         3.646
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  82.00   1.00    1.00    --   40.98 -99.00 -60.00   81
  2  ω     35.00 120.00   1.00    1.20    --  106.95 -61.00-180.00   85
  3  ω     77.00 118.00   1.00    1.20    --  106.95 -30.00-120.00   41
  4  ω     77.00 104.00   1.00    1.20    --  106.95 -95.00-120.00   27
  5  ω     42.00  69.00   1.00    1.20    --  106.95 -30.00-120.00   27
  6  ω     40.00 100.00   1.00    1.20    --  106.95 -45.00 -30.00   60
  7  ω     61.00 109.00   1.00    1.20    --  106.95 -95.00  60.00   48
  8  ω     56.00 106.00   1.00    1.20    --  106.95 -95.00 150.00   50
  9  ω     35.00 124.00   1.00    1.20    --  106.95 -45.00  30.00   89
 10  ω     79.00 152.00   1.00    1.20    --  106.95  30.00 150.00   73
 11  ω     30.00 155.00   1.00    1.20    --  106.95 -15.00 120.00  125
 12  ω     28.00 109.00   1.00    1.20    --  106.95 -95.00 -30.00   81
 13  ω      7.00  49.00   1.00    1.00    --   40.98 -99.00-150.00   42
 14  ω     78.00 107.00   1.00    1.20    --  106.95  61.00-180.00   29
 15  ω    140.00 170.00   1.00    1.20    --  106.95  61.00-180.00   30
 16  ω    -94.00  -6.00   1.00    1.00    --  -40.98 125.00  60.00   88
 17  ω   -115.00 -10.00   1.00    1.00    --  -40.98 -19.00 -30.00  105
 18  ω   -114.00 -38.00   1.00    1.00    --  -40.98 -38.00 -90.00   76
;
_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      -0.0000932000
_diffrn_orient_matrix_UB_12      -0.0916904000
_diffrn_orient_matrix_UB_13      0.1168927000
_diffrn_orient_matrix_UB_21      0.0304259000
_diffrn_orient_matrix_UB_22      -0.1045068000
_diffrn_orient_matrix_UB_23      -0.0496869000
_diffrn_orient_matrix_UB_31      0.1336094000
_diffrn_orient_matrix_UB_32      0.0051726000
_diffrn_orient_matrix_UB_33      -0.0036106000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4395
_reflns_number_total             6351
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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         0.675
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         6351
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0770
_refine_ls_restrained_S_all      1.033
_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)+(0.1170P)²+0.8067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1972
_refine_ls_wR_factor_ref         0.2357
_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) groups
2. Others
 Sof(O2A)=1-FVAR(1)
 Sof(O9)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C3(H3), C4(H4A), C11(H11), C12(H12), C14(H14), N4(H4), C17(H17),
 C18(H18), C26(H26), C27(H27), C29(H29)
3.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O7(H7)
;
_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 0.76657(15) 0.96473(14) 0.18365(12) 0.0665(5) Uani 1 1 d . . . . .
Cl2 Cl 1.01696(12) 0.83887(10) -0.23750(9) 0.0456(3) Uani 1 1 d . . . . .
F1 F 1.0687(2) 0.6841(2) 0.1894(2) 0.0371(6) Uani 1 1 d . . . . .
F2 F 0.9292(3) 0.7489(2) 0.3004(2) 0.0421(7) Uani 1 1 d . . . . .
O1 O 0.7568(3) 0.6684(4) 0.2228(3) 0.0438(8) Uani 1 1 d . . . . .
H1 H 0.707532 0.726386 0.197922 0.066 Uiso 1 1 calc R U . . .
O2 O 0.9071(3) 0.4882(3) 0.1363(2) 0.0355(7) Uani 1 1 d . . . . .
O3 O 1.1601(4) 0.4399(4) 0.1622(3) 0.0627(12) Uani 1 1 d . . . . .
O4 O 1.2484(3) 0.4832(4) 0.2764(4) 0.0619(11) Uani 1 1 d . . . . .
O5 O 1.0168(5) 0.1081(4) 0.5407(4) 0.0712(13) Uani 1 1 d . . . . .
O6 O 0.8595(4) 0.1773(4) 0.6313(3) 0.0669(13) Uani 1 1 d . . . . .
N1 N 0.9508(3) 0.6588(3) -0.0046(3) 0.0312(8) Uani 1 1 d . . . . .
H1A H 0.986111 0.625551 -0.053200 0.037 Uiso 1 1 calc R U . . .
N2 N 1.1629(4) 0.4582(4) 0.2493(3) 0.0398(9) Uani 1 1 d . . . . .
N3 N 0.9429(5) 0.1891(5) 0.5577(4) 0.0549(13) Uani 1 1 d . . . . .
C1 C 0.8762(4) 0.8086(4) 0.0727(4) 0.0315(9) Uani 1 1 d . . . . .
C2 C 0.8387(5) 0.9259(5) 0.0684(4) 0.0449(12) Uani 1 1 d . . . . .
C3 C 0.8544(5) 1.0194(5) -0.0297(5) 0.0520(14) Uani 1 1 d . . . . .
H3 H 0.827871 1.099024 -0.032124 0.062 Uiso 1 1 calc R U . . .
C4 C 0.9101(5) 0.9928(4) -0.1241(4) 0.0447(12) Uani 1 1 d . . . . .
H4A H 0.921701 1.054966 -0.189952 0.054 Uiso 1 1 calc R U . . .
C5 C 0.9484(4) 0.8745(4) -0.1206(4) 0.0339(9) Uani 1 1 d . . . . .
C6 C 0.9295(4) 0.7833(4) -0.0234(4) 0.0302(9) Uani 1 1 d . . . . .
C7 C 0.9096(4) 0.5975(4) 0.0979(3) 0.0300(9) Uani 1 1 d . . . . .
C8 C 0.8683(4) 0.6884(4) 0.1636(3) 0.0310(9) Uani 1 1 d . . . . .
C9 C 0.9604(4) 0.6646(4) 0.2475(4) 0.0303(9) Uani 1 1 d . . . . .
C10 C 0.9662(4) 0.5408(4) 0.3336(3) 0.0303(9) Uani 1 1 d . . . . .
C11 C 0.8743(4) 0.5201(5) 0.4191(4) 0.0388(11) Uani 1 1 d . . . . .
H11 H 0.815948 0.583374 0.425502 0.047 Uiso 1 1 calc R U . . .
C12 C 0.8685(5) 0.4060(5) 0.4950(4) 0.0446(13) Uani 1 1 d . . . . .
H12 H 0.807739 0.392642 0.553084 0.053 Uiso 1 1 calc R U . . .
C13 C 0.9541(5) 0.3130(4) 0.4830(3) 0.0381(11) Uani 1 1 d . . . . .
C14 C 1.0500(4) 0.3305(4) 0.4026(4) 0.0356(10) Uani 1 1 d . . . . .
H14 H 1.109325 0.267357 0.397900 0.043 Uiso 1 1 calc R U . . .
C15 C 1.0544(4) 0.4452(4) 0.3296(3) 0.0312(9) Uani 1 1 d . . . . .
Cl3 Cl 0.60862(17) 0.23938(13) 0.80672(13) 0.0707(5) Uani 1 1 d . . . . .
Cl4 Cl 0.26424(11) 0.64511(11) 0.95098(9) 0.0418(3) Uani 1 1 d . . . . .
F3 F 0.5312(3) 0.7231(3) 0.6810(2) 0.0458(7) Uani 1 1 d . . . . .
F4 F 0.3656(3) 0.8169(3) 0.7368(3) 0.0578(9) Uani 1 1 d . . . . .
O7 O 0.2325(3) 0.6749(3) 0.6897(2) 0.0327(7) Uani 1 1 d . . . . .
H7 H 0.195440 0.629144 0.741760 0.049 Uiso 1 1 calc R U . . .
O8 O 0.3901(3) 0.6163(3) 0.5102(2) 0.0336(7) Uani 1 1 d . . . . .
O10 O 0.6914(4) 0.8239(5) 0.4709(6) 0.0952(19) Uani 1 1 d . . . . .
O11 O 0.4178(9) 1.0773(6) 0.1559(5) 0.127(3) Uani 1 1 d . . . . .
O12 O 0.2652(7) 1.1726(5) 0.2294(6) 0.122(3) Uani 1 1 d . . . . .
N4 N 0.4795(3) 0.4754(3) 0.6561(3) 0.0302(8) Uani 1 1 d . . . . .
H4 H 0.525774 0.431044 0.621486 0.036 Uiso 1 1 calc R U . . .
N5 N 0.6092(4) 0.7817(4) 0.4678(4) 0.0412(10) Uani 1 1 d . . . . .
N6 N 0.3490(9) 1.0893(6) 0.2344(7) 0.095(3) Uani 1 1 d . . . . .
C16 C 0.5136(5) 0.3513(4) 0.8473(4) 0.0436(11) Uani 1 1 d . . . . .
C17 C 0.4775(5) 0.3385(5) 0.9585(4) 0.0475(12) Uani 1 1 d . . . . .
H17 H 0.505493 0.269060 1.012380 0.057 Uiso 1 1 calc R U . . .
C18 C 0.4007(5) 0.4283(5) 0.9888(4) 0.0417(11) Uani 1 1 d . . . . .
H18 H 0.377188 0.418998 1.063159 0.050 Uiso 1 1 calc R U . . .
C19 C 0.3581(4) 0.5322(4) 0.9098(4) 0.0359(10) Uani 1 1 d . . . . .
C20 C 0.3920(4) 0.5450(4) 0.7993(3) 0.0285(9) Uani 1 1 d . . . . .
C21 C 0.4677(4) 0.4519(4) 0.7702(4) 0.0320(9) Uani 1 1 d . . . . .
C22 C 0.3547(4) 0.6396(4) 0.6952(3) 0.0272(8) Uani 1 1 d . . . . .
C23 C 0.4090(4) 0.5766(4) 0.6072(3) 0.0289(9) Uani 1 1 d . . . . .
C24 C 0.4149(4) 0.7559(4) 0.6649(4) 0.0328(10) Uani 1 1 d . . . . .
C25 C 0.4024(4) 0.8423(4) 0.5492(4) 0.0342(10) Uani 1 1 d . . . . .
C26 C 0.2935(5) 0.9146(4) 0.5305(5) 0.0521(14) Uani 1 1 d . . . . .
H26 H 0.233206 0.909203 0.588816 0.063 Uiso 1 1 calc R U . . .
C27 C 0.2731(6) 0.9936(5) 0.4281(7) 0.0662(19) Uani 1 1 d . . . . .
H27 H 0.198909 1.038465 0.415872 0.079 Uiso 1 1 calc R U . . .
C28 C 0.3636(7) 1.0045(5) 0.3455(6) 0.0637(18) Uani 1 1 d . . . . .
C29 C 0.4735(6) 0.9348(5) 0.3577(4) 0.0485(13) Uani 1 1 d . . . . .
H29 H 0.533184 0.942116 0.298747 0.058 Uiso 1 1 calc R U . . .
C30 C 0.4910(4) 0.8540(4) 0.4608(4) 0.0333(9) Uani 1 1 d . . . . .
O9 O 0.6208(6) 0.6679(6) 0.5038(8) 0.057(3) Uani 0.571(13) 1 d . . P A 1
O2A O 0.6196(7) 0.7170(8) 0.4065(9) 0.046(3) Uani 0.429(13) 1 d . . P A 2


_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 1.744(5) . ?
Cl2 C5 1.733(4) . ?
F1 C9 1.358(5) . ?
F2 C9 1.359(5) . ?
O1 H1 0.8200 . ?
O1 C8 1.396(5) . ?
O2 C7 1.226(5) . ?
O3 N2 1.223(6) . ?
O4 N2 1.210(6) . ?
O5 N3 1.217(7) . ?
O6 N3 1.227(6) . ?
N1 H1A 0.8600 . ?
N1 C6 1.396(5) . ?
N1 C7 1.335(5) . ?
N2 C15 1.481(6) . ?
N3 C13 1.478(6) . ?
C1 C2 1.365(6) . ?
C1 C6 1.395(6) . ?
C1 C8 1.520(6) . ?
C2 C3 1.389(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(7) . ?
C4 H4A 0.9300 . ?
C4 C5 1.381(6) . ?
C5 C6 1.372(6) . ?
C7 C8 1.552(5) . ?
C8 C9 1.566(6) . ?
C9 C10 1.516(6) . ?
C10 C11 1.387(6) . ?
C10 C15 1.389(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.374(8) . ?
C13 C14 1.378(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(6) . ?
Cl3 C16 1.730(5) . ?
Cl4 C19 1.737(5) . ?
F3 C24 1.356(5) . ?
F4 C24 1.356(5) . ?
O7 H7 0.8200 . ?
O7 C22 1.399(5) . ?
O8 C23 1.227(5) . ?
O10 N5 1.157(6) . ?
O11 N6 1.212(12) . ?
O12 N6 1.245(11) . ?
N4 H4 0.8600 . ?
N4 C21 1.397(6) . ?
N4 C23 1.348(6) . ?
N5 C30 1.472(6) . ?
N5 O9 1.262(8) . ?
N5 O2A 1.254(9) . ?
N6 C28 1.471(8) . ?
C16 C17 1.395(7) . ?
C16 C21 1.362(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(7) . ?
C19 C20 1.383(6) . ?
C20 C21 1.395(6) . ?
C20 C22 1.507(6) . ?
C22 C23 1.553(5) . ?
C22 C24 1.555(5) . ?
C24 C25 1.520(7) . ?
C25 C26 1.394(7) . ?
C25 C30 1.387(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.373(9) . ?
C27 H27 0.9300 . ?
C27 C28 1.352(10) . ?
C28 C29 1.383(9) . ?
C29 H29 0.9300 . ?
C29 C30 1.382(7) . ?

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
C8 O1 H1 109.5 . . ?
C6 N1 H1A 124.1 . . ?
C7 N1 H1A 124.1 . . ?
C7 N1 C6 111.8(3) . . ?
O3 N2 C15 117.6(4) . . ?
O4 N2 O3 125.2(4) . . ?
O4 N2 C15 117.1(4) . . ?
O5 N3 O6 125.9(5) . . ?
O5 N3 C13 117.4(5) . . ?
O6 N3 C13 116.7(6) . . ?
C2 C1 C6 119.1(4) . . ?
C2 C1 C8 133.5(4) . . ?
C6 C1 C8 107.3(4) . . ?
C1 C2 Cl1 121.9(4) . . ?
C1 C2 C3 120.9(4) . . ?
C3 C2 Cl1 117.2(4) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.3(5) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 C3 120.3(5) . . ?
C5 C4 H4A 119.8 . . ?
C4 C5 Cl2 121.2(4) . . ?
C6 C5 Cl2 119.3(3) . . ?
C6 C5 C4 119.4(4) . . ?
C1 C6 N1 110.4(4) . . ?
C5 C6 N1 128.5(4) . . ?
C5 C6 C1 121.0(4) . . ?
O2 C7 N1 127.1(4) . . ?
O2 C7 C8 124.9(4) . . ?
N1 C7 C8 108.1(4) . . ?
O1 C8 C1 117.0(4) . . ?
O1 C8 C7 110.3(4) . . ?
O1 C8 C9 108.5(3) . . ?
C1 C8 C7 101.6(3) . . ?
C1 C8 C9 111.8(4) . . ?
C7 C8 C9 107.1(3) . . ?
F1 C9 F2 106.9(3) . . ?
F1 C9 C8 108.2(3) . . ?
F1 C9 C10 111.0(3) . . ?
F2 C9 C8 107.5(3) . . ?
F2 C9 C10 108.1(3) . . ?
C10 C9 C8 114.7(3) . . ?
C11 C10 C9 117.7(4) . . ?
C11 C10 C15 117.9(4) . . ?
C15 C10 C9 124.2(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.7(5) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 118.9(4) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 N3 119.3(5) . . ?
C12 C13 C14 122.4(4) . . ?
C14 C13 N3 118.3(5) . . ?
C13 C14 H14 121.4 . . ?
C15 C14 C13 117.2(5) . . ?
C15 C14 H14 121.4 . . ?
C10 C15 N2 123.3(4) . . ?
C14 C15 N2 114.1(4) . . ?
C14 C15 C10 122.7(4) . . ?
C22 O7 H7 109.5 . . ?
C21 N4 H4 124.4 . . ?
C23 N4 H4 124.4 . . ?
C23 N4 C21 111.3(4) . . ?
O10 N5 C30 120.5(4) . . ?
O10 N5 O9 114.6(6) . . ?
O10 N5 O2A 118.2(6) . . ?
O9 N5 C30 121.4(4) . . ?
O2A N5 C30 108.1(5) . . ?
O11 N6 O12 124.4(7) . . ?
O11 N6 C28 120.3(9) . . ?
O12 N6 C28 115.3(9) . . ?
C17 C16 Cl3 121.3(4) . . ?
C21 C16 Cl3 120.1(4) . . ?
C21 C16 C17 118.5(5) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.3(5) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.7(5) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 Cl4 119.5(4) . . ?
C20 C19 Cl4 121.0(4) . . ?
C20 C19 C18 119.5(4) . . ?
C19 C20 C21 119.0(4) . . ?
C19 C20 C22 132.5(4) . . ?
C21 C20 C22 108.2(4) . . ?
C16 C21 N4 127.7(4) . . ?
C16 C21 C20 122.0(4) . . ?
C20 C21 N4 110.1(4) . . ?
O7 C22 C20 117.1(3) . . ?
O7 C22 C23 110.5(3) . . ?
O7 C22 C24 107.7(3) . . ?
C20 C22 C23 101.4(3) . . ?
C20 C22 C24 113.0(3) . . ?
C23 C22 C24 106.5(3) . . ?
O8 C23 N4 127.8(4) . . ?
O8 C23 C22 124.1(4) . . ?
N4 C23 C22 108.1(4) . . ?
F3 C24 F4 106.4(4) . . ?
F3 C24 C22 108.5(3) . . ?
F3 C24 C25 110.5(3) . . ?
F4 C24 C22 108.4(3) . . ?
F4 C24 C25 107.5(4) . . ?
C25 C24 C22 115.1(4) . . ?
C26 C25 C24 117.5(4) . . ?
C30 C25 C24 124.8(4) . . ?
C30 C25 C26 117.7(5) . . ?
C25 C26 H26 119.2 . . ?
C27 C26 C25 121.6(6) . . ?
C27 C26 H26 119.2 . . ?
C26 C27 H27 120.8 . . ?
C28 C27 C26 118.4(6) . . ?
C28 C27 H27 120.8 . . ?
C27 C28 N6 121.4(7) . . ?
C27 C28 C29 123.1(6) . . ?
C29 C28 N6 115.5(7) . . ?
C28 C29 H29 121.3 . . ?
C30 C29 C28 117.4(5) . . ?
C30 C29 H29 121.3 . . ?
C25 C30 N5 123.7(4) . . ?
C29 C30 N5 114.6(4) . . ?
C29 C30 C25 121.7(5) . . ?

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 -179.2(5) . . . . ?
Cl2 C5 C6 N1 -5.1(7) . . . . ?
Cl2 C5 C6 C1 179.0(3) . . . . ?
F1 C9 C10 C11 162.0(4) . . . . ?
F1 C9 C10 C15 -21.3(6) . . . . ?
F2 C9 C10 C11 45.0(5) . . . . ?
F2 C9 C10 C15 -138.4(4) . . . . ?
O1 C8 C9 F1 180.0(3) . . . . ?
O1 C8 C9 F2 -64.9(4) . . . . ?
O1 C8 C9 C10 55.4(5) . . . . ?
O2 C7 C8 O1 -48.2(6) . . . . ?
O2 C7 C8 C1 -173.0(4) . . . . ?
O2 C7 C8 C9 69.6(5) . . . . ?
O3 N2 C15 C10 -92.2(6) . . . . ?
O3 N2 C15 C14 89.7(5) . . . . ?
O4 N2 C15 C10 89.7(6) . . . . ?
O4 N2 C15 C14 -88.4(5) . . . . ?
O5 N3 C13 C12 176.0(5) . . . . ?
O5 N3 C13 C14 -3.2(7) . . . . ?
O6 N3 C13 C12 -3.9(7) . . . . ?
O6 N3 C13 C14 176.9(4) . . . . ?
N1 C7 C8 O1 133.7(4) . . . . ?
N1 C7 C8 C1 8.9(5) . . . . ?
N1 C7 C8 C9 -108.5(4) . . . . ?
N3 C13 C14 C15 175.9(4) . . . . ?
C1 C2 C3 C4 -0.6(9) . . . . ?
C1 C8 C9 F1 -49.5(4) . . . . ?
C1 C8 C9 F2 65.7(4) . . . . ?
C1 C8 C9 C10 -174.1(3) . . . . ?
C2 C1 C6 N1 -174.1(4) . . . . ?
C2 C1 C6 C5 2.4(7) . . . . ?
C2 C1 C8 O1 49.5(7) . . . . ?
C2 C1 C8 C7 169.6(5) . . . . ?
C2 C1 C8 C9 -76.4(7) . . . . ?
C2 C3 C4 C5 0.6(9) . . . . ?
C3 C4 C5 Cl2 179.4(4) . . . . ?
C3 C4 C5 C6 0.9(8) . . . . ?
C4 C5 C6 N1 173.5(5) . . . . ?
C4 C5 C6 C1 -2.4(7) . . . . ?
C6 N1 C7 O2 174.2(4) . . . . ?
C6 N1 C7 C8 -7.8(5) . . . . ?
C6 C1 C2 Cl1 177.7(4) . . . . ?
C6 C1 C2 C3 -0.9(8) . . . . ?
C6 C1 C8 O1 -127.1(4) . . . . ?
C6 C1 C8 C7 -7.0(5) . . . . ?
C6 C1 C8 C9 106.9(4) . . . . ?
C7 N1 C6 C1 3.1(5) . . . . ?
C7 N1 C6 C5 -173.1(4) . . . . ?
C7 C8 C9 F1 61.0(4) . . . . ?
C7 C8 C9 F2 176.1(3) . . . . ?
C7 C8 C9 C10 -63.6(4) . . . . ?
C8 C1 C2 Cl1 1.3(9) . . . . ?
C8 C1 C2 C3 -177.3(5) . . . . ?
C8 C1 C6 N1 3.1(5) . . . . ?
C8 C1 C6 C5 179.7(4) . . . . ?
C8 C9 C10 C11 -74.9(5) . . . . ?
C8 C9 C10 C15 101.7(5) . . . . ?
C9 C10 C11 C12 174.2(4) . . . . ?
C9 C10 C15 N2 9.4(7) . . . . ?
C9 C10 C15 C14 -172.7(4) . . . . ?
C10 C11 C12 C13 -1.3(7) . . . . ?
C11 C10 C15 N2 -174.0(4) . . . . ?
C11 C10 C15 C14 3.9(6) . . . . ?
C11 C12 C13 N3 -174.7(4) . . . . ?
C11 C12 C13 C14 4.5(7) . . . . ?
C12 C13 C14 C15 -3.3(7) . . . . ?
C13 C14 C15 N2 177.1(4) . . . . ?
C13 C14 C15 C10 -1.0(7) . . . . ?
C15 C10 C11 C12 -2.7(7) . . . . ?
Cl3 C16 C17 C18 -179.3(4) . . . . ?
Cl3 C16 C21 N4 5.8(7) . . . . ?
Cl3 C16 C21 C20 -179.1(4) . . . . ?
Cl4 C19 C20 C21 179.9(3) . . . . ?
Cl4 C19 C20 C22 -6.6(7) . . . . ?
F3 C24 C25 C26 -159.4(4) . . . . ?
F3 C24 C25 C30 20.9(6) . . . . ?
F4 C24 C25 C26 -43.7(6) . . . . ?
F4 C24 C25 C30 136.7(4) . . . . ?
O7 C22 C23 O8 47.2(5) . . . . ?
O7 C22 C23 N4 -133.9(4) . . . . ?
O7 C22 C24 F3 173.6(3) . . . . ?
O7 C22 C24 F4 58.4(5) . . . . ?
O7 C22 C24 C25 -62.0(4) . . . . ?
O10 N5 C30 C25 -104.4(6) . . . . ?
O10 N5 C30 C29 76.5(7) . . . . ?
O11 N6 C28 C27 -161.3(7) . . . . ?
O11 N6 C28 C29 16.3(9) . . . . ?
O12 N6 C28 C27 20.7(8) . . . . ?
O12 N6 C28 C29 -161.7(6) . . . . ?
N6 C28 C29 C30 180.0(5) . . . . ?
C16 C17 C18 C19 0.0(8) . . . . ?
C17 C16 C21 N4 -171.1(5) . . . . ?
C17 C16 C21 C20 4.0(7) . . . . ?
C17 C18 C19 Cl4 -178.5(4) . . . . ?
C17 C18 C19 C20 0.8(7) . . . . ?
C18 C19 C20 C21 0.6(7) . . . . ?
C18 C19 C20 C22 174.1(4) . . . . ?
C19 C20 C21 N4 172.7(4) . . . . ?
C19 C20 C21 C16 -3.1(7) . . . . ?
C19 C20 C22 O7 -47.1(6) . . . . ?
C19 C20 C22 C23 -167.5(4) . . . . ?
C19 C20 C22 C24 78.9(6) . . . . ?
C20 C22 C23 O8 172.1(4) . . . . ?
C20 C22 C23 N4 -8.9(4) . . . . ?
C20 C22 C24 F3 42.7(4) . . . . ?
C20 C22 C24 F4 -72.5(5) . . . . ?
C20 C22 C24 C25 167.1(4) . . . . ?
C21 N4 C23 O8 -172.8(4) . . . . ?
C21 N4 C23 C22 8.3(5) . . . . ?
C21 C16 C17 C18 -2.4(8) . . . . ?
C21 C20 C22 O7 126.9(4) . . . . ?
C21 C20 C22 C23 6.5(4) . . . . ?
C21 C20 C22 C24 -107.1(4) . . . . ?
C22 C20 C21 N4 -2.2(5) . . . . ?
C22 C20 C21 C16 -178.1(4) . . . . ?
C22 C24 C25 C26 77.3(5) . . . . ?
C22 C24 C25 C30 -102.4(5) . . . . ?
C23 N4 C21 C16 171.5(5) . . . . ?
C23 N4 C21 C20 -4.0(5) . . . . ?
C23 C22 C24 F3 -67.7(4) . . . . ?
C23 C22 C24 F4 177.0(4) . . . . ?
C23 C22 C24 C25 56.6(5) . . . . ?
C24 C22 C23 O8 -69.5(5) . . . . ?
C24 C22 C23 N4 109.4(4) . . . . ?
C24 C25 C26 C27 -178.7(5) . . . . ?
C24 C25 C30 N5 1.1(7) . . . . ?
C24 C25 C30 C29 -179.8(4) . . . . ?
C25 C26 C27 C28 -3.2(9) . . . . ?
C26 C25 C30 N5 -178.6(4) . . . . ?
C26 C25 C30 C29 0.5(7) . . . . ?
C26 C27 C28 N6 -178.7(6) . . . . ?
C26 C27 C28 C29 3.9(9) . . . . ?
C27 C28 C29 C30 -2.5(8) . . . . ?
C28 C29 C30 N5 179.3(4) . . . . ?
C28 C29 C30 C25 0.2(7) . . . . ?
C30 C25 C26 C27 1.0(8) . . . . ?
O9 N5 C30 C25 53.4(8) . . . . ?
O9 N5 C30 C29 -125.7(7) . . . . ?
O2A N5 C30 C25 115.2(6) . . . . ?
O2A N5 C30 C29 -63.9(7) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.417 0.075 0.937 8.2 2.3 ?
2 0.583 0.925 0.062 8.2 2.4 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.545
_oxdiff_exptl_absorpt_empirical_full_min 0.663
####################################################################### 
# 
# 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_201120-3
_database_code_depnum_ccdc_archive 'CCDC 2116197'
loop_
_audit_author_name
_audit_author_address
ZY
;GNNU
China
;
_audit_update_record             
;
2021-10-18 deposited with the CCDC.	2021-12-16 downloaded from the CCDC.
;
_audit_creation_date             2020-11-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 F2 N3 O5'
_chemical_formula_sum            'C16 H13 F2 N3 O5'
_chemical_formula_weight         365.29
_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                   7.8331(6)
_cell_length_b                   9.3318(8)
_cell_length_c                   12.2430(11)
_cell_angle_alpha                88.789(7)
_cell_angle_beta                 75.495(7)
_cell_angle_gamma                66.796(8)
_cell_volume                     793.29(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2312
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.5570
_cell_measurement_theta_min      3.0400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59871
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_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  0.0206
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5179
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.384
_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    -55.00  39.00   1.00    1.50    --   11.90 -57.00-180.00   94
  2  ω    -12.00  79.00   1.00    1.50    --   11.90  77.00  90.00   91
  3  ω    -11.00  85.00   1.00    1.50    --   11.90  57.00 -30.00   96
;
_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      0.1015362000
_diffrn_orient_matrix_UB_12      -0.0252599000
_diffrn_orient_matrix_UB_13      -0.0175567000
_diffrn_orient_matrix_UB_21      -0.0082886000
_diffrn_orient_matrix_UB_22      0.0710623000
_diffrn_orient_matrix_UB_23      0.0251016000
_diffrn_orient_matrix_UB_31      0.0072386000
_diffrn_orient_matrix_UB_32      -0.0346911000
_diffrn_orient_matrix_UB_33      0.0516742000
_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                2245
_reflns_number_total             2793
_reflns_odcompleteness_completeness 99.94
_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         0.181
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2793
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.022
_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)+(0.0428P)²+0.2417P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1024
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3A), C4(H4), C5(H5A), C11(H11), C12(H12), C14(H14)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O5(H5)
;
_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 0.79378(16) 0.82895(13) 0.19264(10) 0.0388(3) Uani 1 1 d . . . . .
F2 F 0.75026(17) 0.81835(14) 0.02437(9) 0.0402(3) Uani 1 1 d . . . . .
O1 O 0.5037(2) 1.13334(16) 0.12239(11) 0.0349(4) Uani 1 1 d . . . . .
O2 O 0.37784(18) 0.86701(16) 0.10573(10) 0.0286(3) Uani 1 1 d . . . . .
H2 H 0.426360 0.882849 0.041610 0.043 Uiso 1 1 calc R U . . .
O3 O 0.8266(3) 0.6191(3) 0.37733(14) 0.0800(7) Uani 1 1 d . . . . .
O4 O 1.0935(3) 0.5700(2) 0.25191(16) 0.0612(5) Uani 1 1 d . . . . .
O5 O 0.9842(2) 0.04217(17) 0.20377(12) 0.0398(4) Uani 1 1 d . . . . .
H5 H 1.096249 -0.020903 0.180437 0.060 Uiso 1 1 calc R U . . .
N1 N 0.3862(2) 1.10133(19) 0.30845(13) 0.0335(4) Uani 1 1 d . . . . .
N2 N 0.9323(3) 0.5735(2) 0.28322(15) 0.0400(5) Uani 1 1 d . . . . .
N3 N 0.9188(3) 0.1188(2) 0.11261(14) 0.0339(4) Uani 1 1 d . . . . .
H3 H 0.836(3) 0.090(3) 0.0980(19) 0.043(7) Uiso 1 1 d . . . . .
C1 C 0.3473(3) 0.9827(2) 0.37057(16) 0.0330(5) Uani 1 1 d . . . . .
C2 C 0.2650(3) 0.9899(3) 0.48489(17) 0.0457(6) Uani 1 1 d . . . . .
H2A H 0.231660 1.077894 0.533093 0.055 Uiso 1 1 calc R U . . .
C3 C 0.2340(4) 0.8590(3) 0.52472(18) 0.0534(7) Uani 1 1 d . . . . .
H3A H 0.179711 0.859454 0.601598 0.064 Uiso 1 1 calc R U . . .
C4 C 0.2813(4) 0.7290(3) 0.45382(19) 0.0513(6) Uani 1 1 d . . . . .
H4 H 0.257353 0.644005 0.483120 0.062 Uiso 1 1 calc R U . . .
C5 C 0.3647(3) 0.7238(3) 0.33852(17) 0.0402(5) Uani 1 1 d . . . . .
H5A H 0.396445 0.636412 0.290144 0.048 Uiso 1 1 calc R U . . .
C6 C 0.3989(3) 0.8513(2) 0.29794(15) 0.0296(5) Uani 1 1 d . . . . .
C7 C 0.4818(3) 0.8830(2) 0.17987(15) 0.0258(4) Uani 1 1 d . . . . .
C8 C 0.4600(3) 1.0549(2) 0.19698(16) 0.0290(5) Uani 1 1 d . . . . .
C9 C 0.6988(3) 0.7795(2) 0.13279(15) 0.0280(4) Uani 1 1 d . . . . .
C10 C 0.7602(3) 0.6065(2) 0.13068(15) 0.0259(4) Uani 1 1 d . . . . .
C11 C 0.7124(3) 0.5289(2) 0.05362(16) 0.0315(5) Uani 1 1 d . . . . .
H11 H 0.646155 0.586688 0.003315 0.038 Uiso 1 1 calc R U . . .
C12 C 0.7603(3) 0.3711(2) 0.05026(16) 0.0321(5) Uani 1 1 d . . . . .
H12 H 0.725749 0.323956 -0.001774 0.039 Uiso 1 1 calc R U . . .
C13 C 0.8607(3) 0.2796(2) 0.12410(15) 0.0269(4) Uani 1 1 d . . . . .
C14 C 0.9138(3) 0.3516(2) 0.19952(15) 0.0284(4) Uani 1 1 d . . . . .
H14 H 0.982969 0.293246 0.248408 0.034 Uiso 1 1 calc R U . . .
C15 C 0.8629(3) 0.5110(2) 0.20131(15) 0.0273(4) Uani 1 1 d . . . . .
C16 C 0.3456(4) 1.2558(3) 0.35758(19) 0.0499(6) Uani 1 1 d . . . . .
H16A H 0.379654 1.316904 0.298691 0.075 Uiso 1 1 calc R U . . .
H16B H 0.419498 1.245406 0.411349 0.075 Uiso 1 1 calc R U . . .
H16C H 0.210916 1.307074 0.395077 0.075 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 C9 1.364(2) . ?
F2 C9 1.372(2) . ?
O1 C8 1.224(2) . ?
O2 H2 0.8200 . ?
O2 C7 1.407(2) . ?
O3 N2 1.208(2) . ?
O4 N2 1.212(2) . ?
O5 H5 0.8200 . ?
O5 N3 1.409(2) . ?
N1 C1 1.418(3) . ?
N1 C8 1.348(2) . ?
N1 C16 1.457(3) . ?
N2 C15 1.480(2) . ?
N3 H3 0.85(2) . ?
N3 C13 1.384(3) . ?
C1 C2 1.377(3) . ?
C1 C6 1.390(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.392(3) . ?
C3 H3A 0.9300 . ?
C3 C4 1.375(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.392(3) . ?
C5 H5A 0.9300 . ?
C5 C6 1.376(3) . ?
C6 C7 1.504(3) . ?
C7 C8 1.558(3) . ?
C7 C9 1.547(3) . ?
C9 C10 1.491(3) . ?
C10 C11 1.405(3) . ?
C10 C15 1.392(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.368(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.400(3) . ?
C13 C14 1.384(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C7 O2 H2 109.5 . . ?
N3 O5 H5 109.5 . . ?
C1 N1 C16 124.62(17) . . ?
C8 N1 C1 111.33(16) . . ?
C8 N1 C16 124.01(19) . . ?
O3 N2 O4 124.98(19) . . ?
O3 N2 C15 117.5(2) . . ?
O4 N2 C15 117.45(17) . . ?
O5 N3 H3 110.5(16) . . ?
C13 N3 O5 114.01(15) . . ?
C13 N3 H3 113.9(16) . . ?
C2 C1 N1 127.9(2) . . ?
C2 C1 C6 122.1(2) . . ?
C6 C1 N1 110.01(16) . . ?
C1 C2 H2A 121.6 . . ?
C1 C2 C3 116.7(2) . . ?
C3 C2 H2A 121.6 . . ?
C2 C3 H3A 119.0 . . ?
C4 C3 C2 122.0(2) . . ?
C4 C3 H3A 119.0 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.5(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5A 120.8 . . ?
C6 C5 C4 118.3(2) . . ?
C6 C5 H5A 120.8 . . ?
C1 C6 C7 108.40(17) . . ?
C5 C6 C1 120.40(18) . . ?
C5 C6 C7 131.15(17) . . ?
O2 C7 C6 110.85(15) . . ?
O2 C7 C8 112.25(15) . . ?
O2 C7 C9 110.30(14) . . ?
C6 C7 C8 102.29(14) . . ?
C6 C7 C9 113.26(16) . . ?
C9 C7 C8 107.65(15) . . ?
O1 C8 N1 126.14(18) . . ?
O1 C8 C7 125.98(16) . . ?
N1 C8 C7 107.88(17) . . ?
F1 C9 F2 105.69(15) . . ?
F1 C9 C7 106.69(14) . . ?
F1 C9 C10 111.16(15) . . ?
F2 C9 C7 106.09(15) . . ?
F2 C9 C10 108.91(14) . . ?
C10 C9 C7 117.56(16) . . ?
C11 C10 C9 119.62(17) . . ?
C15 C10 C9 125.05(16) . . ?
C15 C10 C11 115.33(18) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 C10 122.04(19) . . ?
C12 C11 H11 119.0 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.88(17) . . ?
C13 C12 H12 119.6 . . ?
N3 C13 C12 119.11(17) . . ?
N3 C13 C14 122.02(18) . . ?
C14 C13 C12 118.60(18) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.23(18) . . ?
C15 C14 H14 120.4 . . ?
C10 C15 N2 121.96(17) . . ?
C14 C15 N2 114.12(17) . . ?
C14 C15 C10 123.89(17) . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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 C9 C10 C11 -165.93(16) . . . . ?
F1 C9 C10 C15 14.7(3) . . . . ?
F2 C9 C10 C11 -49.9(2) . . . . ?
F2 C9 C10 C15 130.76(19) . . . . ?
O2 C7 C8 O1 -58.9(2) . . . . ?
O2 C7 C8 N1 121.66(17) . . . . ?
O2 C7 C9 F1 165.46(14) . . . . ?
O2 C7 C9 F2 53.11(19) . . . . ?
O2 C7 C9 C10 -69.0(2) . . . . ?
O3 N2 C15 C10 90.2(3) . . . . ?
O3 N2 C15 C14 -91.7(2) . . . . ?
O4 N2 C15 C10 -92.3(2) . . . . ?
O4 N2 C15 C14 85.9(2) . . . . ?
O5 N3 C13 C12 -168.28(16) . . . . ?
O5 N3 C13 C14 17.7(3) . . . . ?
N1 C1 C2 C3 177.1(2) . . . . ?
N1 C1 C6 C5 -176.54(18) . . . . ?
N1 C1 C6 C7 1.3(2) . . . . ?
N3 C13 C14 C15 175.42(18) . . . . ?
C1 N1 C8 O1 178.35(18) . . . . ?
C1 N1 C8 C7 -2.2(2) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C1 C6 C7 O2 -122.28(17) . . . . ?
C1 C6 C7 C8 -2.4(2) . . . . ?
C1 C6 C7 C9 113.13(18) . . . . ?
C2 C1 C6 C5 1.4(3) . . . . ?
C2 C1 C6 C7 179.31(19) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C4 C5 C6 C7 -178.6(2) . . . . ?
C5 C6 C7 O2 55.3(3) . . . . ?
C5 C6 C7 C8 175.1(2) . . . . ?
C5 C6 C7 C9 -69.3(3) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
C6 C7 C8 O1 -177.74(19) . . . . ?
C6 C7 C8 N1 2.80(19) . . . . ?
C6 C7 C9 F1 -69.6(2) . . . . ?
C6 C7 C9 F2 178.00(14) . . . . ?
C6 C7 C9 C10 55.9(2) . . . . ?
C7 C9 C10 C11 70.7(2) . . . . ?
C7 C9 C10 C15 -108.6(2) . . . . ?
C8 N1 C1 C2 -177.2(2) . . . . ?
C8 N1 C1 C6 0.6(2) . . . . ?
C8 C7 C9 F1 42.68(19) . . . . ?
C8 C7 C9 F2 -69.67(17) . . . . ?
C8 C7 C9 C10 168.25(15) . . . . ?
C9 C7 C8 O1 62.7(2) . . . . ?
C9 C7 C8 N1 -116.77(16) . . . . ?
C9 C10 C11 C12 -178.11(18) . . . . ?
C9 C10 C15 N2 -3.7(3) . . . . ?
C9 C10 C15 C14 178.32(17) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C10 C15 N2 176.95(17) . . . . ?
C11 C10 C15 C14 -1.1(3) . . . . ?
C11 C12 C13 N3 -175.36(18) . . . . ?
C11 C12 C13 C14 -1.1(3) . . . . ?
C12 C13 C14 C15 1.4(3) . . . . ?
C13 C14 C15 N2 -178.41(17) . . . . ?
C13 C14 C15 C10 -0.3(3) . . . . ?
C15 C10 C11 C12 1.3(3) . . . . ?
C16 N1 C1 C2 0.7(3) . . . . ?
C16 N1 C1 C6 178.56(19) . . . . ?
C16 N1 C8 O1 0.4(3) . . . . ?
C16 N1 C8 C7 179.84(18) . . . . ?

_olex2_date_sample_data_collection 2020-11-24
_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 1.467
_oxdiff_exptl_absorpt_empirical_full_min 0.477
####################################################################### 
# 
# 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_gn1213
_database_code_depnum_ccdc_archive 'CCDC 2128249'
loop_
_audit_author_name
_audit_author_address
Lai
;GNNU
China
;
_audit_update_record             
;
2021-12-13 deposited with the CCDC.	2021-12-16 downloaded from the CCDC.
;
_audit_creation_date             2021-12-13
_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         'C16 H10 F2 N2 O4'
_chemical_formula_sum            'C16 H10 F2 N2 O4'
_chemical_formula_weight         332.26
_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                   7.8185(5)
_cell_length_b                   8.7925(7)
_cell_length_c                   11.6820(7)
_cell_angle_alpha                92.612(6)
_cell_angle_beta                 101.796(5)
_cell_angle_gamma                112.885(6)
_cell_volume                     717.23(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2218
_cell_measurement_temperature    219.99(10)
_cell_measurement_theta_max      28.4420
_cell_measurement_theta_min      2.8950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65458
_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    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4587
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.989
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_min         2.539
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      219.99(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    -54.00  35.00   1.00    2.00    --   11.90 -57.00  90.00   89
  2  ω    -13.00  75.00   1.00    2.00    --   11.90  77.00   0.00   88
  3  ω    -14.00  85.00   1.00    2.00    --   11.90  57.00-120.00   99
;
_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      0.0099298000
_diffrn_orient_matrix_UB_12      0.0250108000
_diffrn_orient_matrix_UB_13      -0.0560096000
_diffrn_orient_matrix_UB_21      0.0136526000
_diffrn_orient_matrix_UB_22      0.0816593000
_diffrn_orient_matrix_UB_23      0.0215270000
_diffrn_orient_matrix_UB_31      0.1000586000
_diffrn_orient_matrix_UB_32      0.0228902000
_diffrn_orient_matrix_UB_33      0.0179528000
_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                2068
_reflns_number_total             2531
_reflns_odcompleteness_completeness 99.97
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2531
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.039
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0596P)²+0.0768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1170
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(O4)=1-FVAR(1)
 Sof(O5)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C14(H14), C15(H15)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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 -0.12086(14) 0.23371(14) 0.68812(9) 0.0397(3) Uani 1 1 d . . . . .
F2 F -0.00746(15) 0.47845(13) 0.63486(9) 0.0403(3) Uani 1 1 d . . . . .
O1 O 0.1759(2) 0.12755(17) 0.82230(13) 0.0482(4) Uani 1 1 d . . . . .
O2 O 0.37651(17) 0.43725(17) 0.73075(11) 0.0361(4) Uani 1 1 d . . . . .
O3 O 0.3796(2) 0.09745(19) 0.28305(13) 0.0489(4) Uani 1 1 d . . . . .
O4 O 0.6288(13) 0.243(3) 0.4225(9) 0.058(4) Uani 0.53(7) 1 d . . P A 2
O5 O 0.604(4) 0.166(8) 0.438(2) 0.090(8) Uani 0.47(7) 1 d . . P A 1
N1 N 0.2088(2) 0.33042(19) 0.96725(13) 0.0341(4) Uani 1 1 d . . . . .
N2 N 0.4517(3) 0.1698(2) 0.38219(16) 0.0454(5) Uani 1 1 d . . . . .
C1 C 0.2361(2) 0.5512(2) 0.86322(16) 0.0291(4) Uani 1 1 d . . . . .
C2 C 0.2605(3) 0.7125(2) 0.84945(18) 0.0358(5) Uani 1 1 d . . . . .
H2 H 0.260739 0.748358 0.775786 0.043 Uiso 1 1 calc R U . . .
C3 C 0.2847(3) 0.8205(3) 0.94769(19) 0.0424(5) Uani 1 1 d . . . . .
H3 H 0.300546 0.929610 0.939675 0.051 Uiso 1 1 calc R U . . .
C4 C 0.2855(3) 0.7677(3) 1.05696(19) 0.0444(5) Uani 1 1 d . . . . .
H4 H 0.303868 0.842566 1.121819 0.053 Uiso 1 1 calc R U . . .
C5 C 0.2595(3) 0.6046(3) 1.07255(18) 0.0392(5) Uani 1 1 d . . . . .
H5 H 0.258255 0.568540 1.146123 0.047 Uiso 1 1 calc R U . . .
C6 C 0.2358(2) 0.4994(2) 0.97439(16) 0.0304(4) Uani 1 1 d . . . . .
C7 C 0.1927(3) 0.2665(2) 0.85570(17) 0.0334(5) Uani 1 1 d . . . . .
C8 C 0.2091(2) 0.4079(2) 0.77769(16) 0.0299(4) Uani 1 1 d . . . . .
C9 C 0.0411(3) 0.3500(2) 0.66701(16) 0.0300(4) Uani 1 1 d . . . . .
C10 C 0.1167(2) 0.2899(2) 0.57526(16) 0.0287(4) Uani 1 1 d . . . . .
C11 C 0.3121(2) 0.3448(2) 0.62066(16) 0.0304(4) Uani 1 1 d . . . . .
C12 C 0.4280(3) 0.3093(3) 0.56010(17) 0.0369(5) Uani 1 1 d . . . . .
H12 H 0.558886 0.345276 0.591008 0.044 Uiso 1 1 calc R U . . .
C13 C 0.3363(3) 0.2163(2) 0.44972(17) 0.0339(5) Uani 1 1 d . . . . .
C14 C 0.1416(3) 0.1605(2) 0.40002(16) 0.0321(4) Uani 1 1 d . . . . .
H14 H 0.087292 0.099092 0.325067 0.038 Uiso 1 1 calc R U . . .
C15 C 0.0302(3) 0.1985(2) 0.46485(16) 0.0308(4) Uani 1 1 d . . . . .
H15 H -0.100737 0.162913 0.434317 0.037 Uiso 1 1 calc R U . . .
C16 C 0.2117(3) 0.2391(3) 1.06739(18) 0.0436(5) Uani 1 1 d . . . . .
H16A H 0.333687 0.292599 1.122918 0.065 Uiso 1 1 calc R U . . .
H16B H 0.190903 0.126968 1.040806 0.065 Uiso 1 1 calc R U . . .
H16C H 0.112544 0.237287 1.104756 0.065 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 C9 1.361(2) . ?
F2 C9 1.369(2) . ?
O1 C7 1.214(2) . ?
O2 C8 1.457(2) . ?
O2 C11 1.375(2) . ?
O3 N2 1.205(2) . ?
O4 N2 1.251(9) . ?
O5 N2 1.249(15) . ?
N1 C6 1.413(2) . ?
N1 C7 1.357(2) . ?
N1 C16 1.450(3) . ?
N2 C13 1.466(2) . ?
C1 C2 1.377(3) . ?
C1 C6 1.396(3) . ?
C1 C8 1.491(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.394(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(3) . ?
C7 C8 1.556(3) . ?
C8 C9 1.544(3) . ?
C9 C10 1.493(2) . ?
C10 C11 1.385(3) . ?
C10 C15 1.376(2) . ?
C11 C12 1.371(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(3) . ?
C13 C14 1.389(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.384(3) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C11 O2 C8 106.92(13) . . ?
C6 N1 C16 124.65(16) . . ?
C7 N1 C6 111.50(16) . . ?
C7 N1 C16 123.71(17) . . ?
O3 N2 O4 123.0(5) . . ?
O3 N2 O5 119.6(7) . . ?
O3 N2 C13 119.76(17) . . ?
O4 N2 C13 115.1(7) . . ?
O5 N2 C13 118.0(7) . . ?
C2 C1 C6 119.90(17) . . ?
C2 C1 C8 131.82(18) . . ?
C6 C1 C8 108.28(16) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.69(19) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.65(19) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.53(19) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 121.5 . . ?
C6 C5 C4 117.0(2) . . ?
C6 C5 H5 121.5 . . ?
C1 C6 N1 109.93(16) . . ?
C5 C6 N1 127.87(18) . . ?
C5 C6 C1 122.20(18) . . ?
O1 C7 N1 127.19(19) . . ?
O1 C7 C8 125.59(18) . . ?
N1 C7 C8 107.16(16) . . ?
O2 C8 C1 112.57(14) . . ?
O2 C8 C7 106.47(14) . . ?
O2 C8 C9 104.15(13) . . ?
C1 C8 C7 103.13(15) . . ?
C1 C8 C9 118.65(15) . . ?
C9 C8 C7 111.46(15) . . ?
F1 C9 F2 104.60(14) . . ?
F1 C9 C8 111.48(14) . . ?
F1 C9 C10 114.70(15) . . ?
F2 C9 C8 111.30(14) . . ?
F2 C9 C10 111.47(14) . . ?
C10 C9 C8 103.49(14) . . ?
C11 C10 C9 106.57(16) . . ?
C15 C10 C9 132.61(16) . . ?
C15 C10 C11 120.82(16) . . ?
O2 C11 C10 113.58(15) . . ?
C12 C11 O2 123.97(16) . . ?
C12 C11 C10 122.45(17) . . ?
C11 C12 H12 122.4 . . ?
C11 C12 C13 115.27(17) . . ?
C13 C12 H12 122.4 . . ?
C12 C13 N2 117.82(17) . . ?
C12 C13 C14 124.29(17) . . ?
C14 C13 N2 117.87(17) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 C13 118.33(17) . . ?
C15 C14 H14 120.8 . . ?
C10 C15 C14 118.83(17) . . ?
C10 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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 C9 C10 C11 -134.31(17) . . . . ?
F1 C9 C10 C15 45.7(3) . . . . ?
F2 C9 C10 C11 107.06(17) . . . . ?
F2 C9 C10 C15 -72.9(3) . . . . ?
O1 C7 C8 O2 -58.7(2) . . . . ?
O1 C7 C8 C1 -177.34(18) . . . . ?
O1 C7 C8 C9 54.3(2) . . . . ?
O2 C8 C9 F1 145.06(14) . . . . ?
O2 C8 C9 F2 -98.57(16) . . . . ?
O2 C8 C9 C10 21.27(18) . . . . ?
O2 C11 C12 C13 -179.16(18) . . . . ?
O3 N2 C13 C12 -175.61(19) . . . . ?
O3 N2 C13 C14 6.0(3) . . . . ?
O4 N2 C13 C12 -11.5(13) . . . . ?
O4 N2 C13 C14 170.0(13) . . . . ?
O5 N2 C13 C12 23(3) . . . . ?
O5 N2 C13 C14 -155(3) . . . . ?
N1 C7 C8 O2 118.84(15) . . . . ?
N1 C7 C8 C1 0.17(19) . . . . ?
N1 C7 C8 C9 -128.20(15) . . . . ?
N2 C13 C14 C15 177.71(17) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C1 C8 C9 F1 -88.87(19) . . . . ?
C1 C8 C9 F2 27.5(2) . . . . ?
C1 C8 C9 C10 147.33(16) . . . . ?
C2 C1 C6 N1 -179.95(16) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C1 C8 O2 65.2(3) . . . . ?
C2 C1 C8 C7 179.58(19) . . . . ?
C2 C1 C8 C9 -56.7(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C4 C5 C6 N1 179.44(17) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C6 N1 C7 O1 177.00(18) . . . . ?
C6 N1 C7 C8 -0.5(2) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C6 C1 C8 O2 -114.15(17) . . . . ?
C6 C1 C8 C7 0.19(19) . . . . ?
C6 C1 C8 C9 123.93(17) . . . . ?
C7 N1 C6 C1 0.6(2) . . . . ?
C7 N1 C6 C5 -179.28(19) . . . . ?
C7 C8 C9 F1 30.7(2) . . . . ?
C7 C8 C9 F2 147.03(14) . . . . ?
C7 C8 C9 C10 -93.14(16) . . . . ?
C8 O2 C11 C10 15.7(2) . . . . ?
C8 O2 C11 C12 -164.45(18) . . . . ?
C8 C1 C2 C3 -179.26(18) . . . . ?
C8 C1 C6 N1 -0.5(2) . . . . ?
C8 C1 C6 C5 179.42(17) . . . . ?
C8 C9 C10 C11 -12.66(19) . . . . ?
C8 C9 C10 C15 167.38(19) . . . . ?
C9 C10 C11 O2 -1.3(2) . . . . ?
C9 C10 C11 C12 178.89(18) . . . . ?
C9 C10 C15 C14 -179.34(18) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C11 O2 C8 C1 -152.35(16) . . . . ?
C11 O2 C8 C7 95.36(16) . . . . ?
C11 O2 C8 C9 -22.55(18) . . . . ?
C11 C10 C15 C14 0.7(3) . . . . ?
C11 C12 C13 N2 -178.11(17) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C10 0.1(3) . . . . ?
C15 C10 C11 O2 178.70(16) . . . . ?
C15 C10 C11 C12 -1.1(3) . . . . ?
C16 N1 C6 C1 176.39(17) . . . . ?
C16 N1 C6 C5 -3.5(3) . . . . ?
C16 N1 C7 O1 1.2(3) . . . . ?
C16 N1 C7 C8 -176.29(17) . . . . ?

_olex2_date_sample_data_collection 2021-12-13
_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 1.740
_oxdiff_exptl_absorpt_empirical_full_min 0.692
