# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

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

data_r20220603a
_database_code_depnum_ccdc_archive 'CCDC 2235337'
loop_
_audit_author_name
_audit_author_address
MO-I
;Tianjin university
China
;
_audit_update_record             
;
2023-01-10 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;
_audit_creation_date             2022-07-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 F6 N O2'
_chemical_formula_sum            'C16 H11 F6 N O2'
_chemical_formula_weight         363.26
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   4.8810(2)
_cell_length_b                   36.8398(13)
_cell_length_c                   8.6324(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.518(4)
_cell_angle_gamma                90
_cell_volume                     1502.67(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4168
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      31.0060
_cell_measurement_theta_min      2.2040
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_k_min       -51
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8272
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.235
_diffrn_reflns_theta_min         2.211
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   0.50    1.00    --  -30.00  45.00   0.00  360
  2  ω   -120.00  55.00   0.50    1.00    --  -30.00  45.00  90.00  350
  3  ω   -120.00  50.00   0.50    1.00    --  -30.00  45.00 180.00  340
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn70'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0314246000
_diffrn_orient_matrix_UB_12      0.0023331000
_diffrn_orient_matrix_UB_13      -0.0841948000
_diffrn_orient_matrix_UB_21      0.0046131000
_diffrn_orient_matrix_UB_22      -0.0190860000
_diffrn_orient_matrix_UB_23      -0.0101097000
_diffrn_orient_matrix_UB_31      -0.1466275000
_diffrn_orient_matrix_UB_32      -0.0011033000
_diffrn_orient_matrix_UB_33      -0.0040402000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_full    0.949
_reflns_Friedel_fraction_max     0.824
_reflns_number_gt                3327
_reflns_number_total             4280
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 1159 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(5)
_refine_ls_extinction_coef       0.005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4280
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0605
_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)+(0.0915P)²+0.4247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1772
_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:
 C3(H3), C5(H5), C7(H7), C9(H9), C12(H12), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 -0.2316(7) 0.58495(10) 0.0810(3) 0.0556(8) Uani 1 1 d . . . . .
F2 F -0.4665(7) 0.62263(8) 0.1878(3) 0.0549(9) Uani 1 1 d . . . . .
F3 F -0.5695(6) 0.56626(8) 0.1783(4) 0.0520(8) Uani 1 1 d . . . . .
F4 F -0.1643(15) 0.49737(12) 0.6582(5) 0.122(2) Uani 1 1 d . . . . .
F5 F -0.0975(12) 0.53517(10) 0.8388(5) 0.0934(16) Uani 1 1 d . . . . .
F6 F 0.2457(10) 0.50883(15) 0.7935(8) 0.126(2) Uani 1 1 d . . . . .
O1 O 0.7269(6) 0.68894(8) 0.4822(3) 0.0372(7) Uani 1 1 d . . . . .
H1 H 0.599828 0.673493 0.481057 0.056 Uiso 1 1 calc R U . . .
O2 O 1.5643(6) 0.73565(8) 0.8368(3) 0.0325(6) Uani 1 1 d . . . . .
N1 N 0.4886(7) 0.63318(8) 0.5794(3) 0.0269(6) Uani 1 1 d . . . . .
C1 C -0.3541(10) 0.58907(12) 0.2028(5) 0.0364(9) Uani 1 1 d . . . . .
C2 C -0.1464(8) 0.58460(10) 0.3617(4) 0.0271(7) Uani 1 1 d . . . . .
C3 C -0.1686(9) 0.55598(10) 0.4628(4) 0.0287(7) Uani 1 1 d . . . . .
H3 H -0.317596 0.538779 0.433244 0.034 Uiso 1 1 calc R U . . .
C4 C 0.0335(8) 0.55314(9) 0.6087(4) 0.0284(7) Uani 1 1 d . . . . .
C5 C 0.2524(8) 0.57772(10) 0.6533(4) 0.0285(7) Uani 1 1 d . . . . .
H5 H 0.387858 0.575123 0.753056 0.034 Uiso 1 1 calc R U . . .
C6 C 0.2745(8) 0.60666(9) 0.5506(4) 0.0257(7) Uani 1 1 d . . . . .
C7 C 0.0712(8) 0.60967(10) 0.4049(4) 0.0281(7) Uani 1 1 d . . . . .
H7 H 0.082364 0.629141 0.334636 0.034 Uiso 1 1 calc R U . . .
C8 C 0.0092(10) 0.52335(11) 0.7228(5) 0.0348(8) Uani 1 1 d . . . . .
C9 C 0.6827(8) 0.63449(9) 0.7132(4) 0.0285(7) Uani 1 1 d . . . . .
H9 H 0.678788 0.617296 0.794645 0.034 Uiso 1 1 calc R U . . .
C10 C 0.9032(8) 0.66132(10) 0.7412(4) 0.0265(7) Uani 1 1 d . . . . .
C11 C 0.9202(8) 0.68778(10) 0.6251(4) 0.0266(7) Uani 1 1 d . . . . .
C12 C 1.1379(8) 0.71315(10) 0.6541(4) 0.0272(7) Uani 1 1 d . . . . .
H12 H 1.147341 0.730798 0.575331 0.033 Uiso 1 1 calc R U . . .
C13 C 1.3420(8) 0.71250(9) 0.7993(4) 0.0271(7) Uani 1 1 d . . . . .
C14 C 1.3274(9) 0.68653(10) 0.9166(4) 0.0310(8) Uani 1 1 d . . . . .
H14 H 1.466095 0.686310 1.015892 0.037 Uiso 1 1 calc R U . . .
C15 C 1.1140(9) 0.66175(10) 0.8871(4) 0.0309(8) Uani 1 1 d . . . . .
H15 H 1.106438 0.644266 0.966772 0.037 Uiso 1 1 calc R U . . .
C16 C 1.5764(9) 0.76457(11) 0.7267(5) 0.0357(9) Uani 1 1 d . . . . .
H16A H 1.575178 0.754309 0.621792 0.054 Uiso 1 1 calc R U . . .
H16B H 1.750300 0.778608 0.766725 0.054 Uiso 1 1 calc R U . . .
H16C H 1.411953 0.780480 0.716604 0.054 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 C1 1.342(5) . ?
F2 C1 1.346(5) . ?
F3 C1 1.321(5) . ?
F4 C8 1.307(6) . ?
F5 C8 1.313(6) . ?
F6 C8 1.280(6) . ?
O1 H1 0.8400 . ?
O1 C11 1.353(4) . ?
O2 C13 1.354(4) . ?
O2 C16 1.439(5) . ?
N1 C6 1.407(5) . ?
N1 C9 1.298(4) . ?
C1 C2 1.496(5) . ?
C2 C3 1.390(5) . ?
C2 C7 1.386(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(5) . ?
C4 C5 1.380(5) . ?
C4 C8 1.500(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.408(5) . ?
C6 C7 1.397(5) . ?
C7 H7 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.436(5) . ?
C10 C11 1.415(5) . ?
C10 C15 1.413(5) . ?
C11 C12 1.390(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.392(5) . ?
C13 C14 1.408(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.360(6) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C11 O1 H1 109.5 . . ?
C13 O2 C16 118.1(3) . . ?
C9 N1 C6 121.8(3) . . ?
F1 C1 F2 106.3(3) . . ?
F1 C1 C2 111.9(4) . . ?
F2 C1 C2 110.8(3) . . ?
F3 C1 F1 107.2(3) . . ?
F3 C1 F2 106.3(4) . . ?
F3 C1 C2 114.0(3) . . ?
C3 C2 C1 121.2(3) . . ?
C7 C2 C1 118.1(3) . . ?
C7 C2 C3 120.7(3) . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.3(3) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 C8 119.6(4) . . ?
C5 C4 C3 121.7(3) . . ?
C5 C4 C8 118.7(3) . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
N1 C6 C5 125.8(3) . . ?
C7 C6 N1 115.6(3) . . ?
C7 C6 C5 118.5(3) . . ?
C2 C7 C6 120.9(3) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
F4 C8 F5 103.3(5) . . ?
F4 C8 C4 113.9(3) . . ?
F5 C8 C4 111.7(4) . . ?
F6 C8 F4 107.9(5) . . ?
F6 C8 F5 104.9(5) . . ?
F6 C8 C4 114.1(4) . . ?
N1 C9 H9 119.2 . . ?
N1 C9 C10 121.6(3) . . ?
C10 C9 H9 119.2 . . ?
C11 C10 C9 122.0(3) . . ?
C15 C10 C9 120.3(3) . . ?
C15 C10 C11 117.7(3) . . ?
O1 C11 C10 121.1(3) . . ?
O1 C11 C12 118.0(3) . . ?
C12 C11 C10 120.9(3) . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.5(3) . . ?
C13 C12 H12 120.2 . . ?
O2 C13 C12 123.7(3) . . ?
O2 C13 C14 116.0(3) . . ?
C12 C13 C14 120.4(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14 120.1 . . ?
C10 C15 H15 119.1 . . ?
C14 C15 C10 121.8(3) . . ?
C14 C15 H15 119.1 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 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 C1 C2 C3 -114.8(4) . . . . ?
F1 C1 C2 C7 64.6(5) . . . . ?
F2 C1 C2 C3 126.8(4) . . . . ?
F2 C1 C2 C7 -53.8(5) . . . . ?
F3 C1 C2 C3 7.0(6) . . . . ?
F3 C1 C2 C7 -173.6(4) . . . . ?
O1 C11 C12 C13 -179.4(3) . . . . ?
O2 C13 C14 C15 -178.6(3) . . . . ?
N1 C6 C7 C2 178.5(3) . . . . ?
N1 C9 C10 C11 0.3(5) . . . . ?
N1 C9 C10 C15 -179.1(3) . . . . ?
C1 C2 C3 C4 179.4(4) . . . . ?
C1 C2 C7 C6 -179.0(3) . . . . ?
C2 C3 C4 C5 -0.4(6) . . . . ?
C2 C3 C4 C8 177.8(3) . . . . ?
C3 C2 C7 C6 0.4(6) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C3 C4 C8 F4 15.5(6) . . . . ?
C3 C4 C8 F5 -101.1(5) . . . . ?
C3 C4 C8 F6 140.1(5) . . . . ?
C4 C5 C6 N1 -178.7(3) . . . . ?
C4 C5 C6 C7 0.1(5) . . . . ?
C5 C4 C8 F4 -166.3(5) . . . . ?
C5 C4 C8 F5 77.2(6) . . . . ?
C5 C4 C8 F6 -41.7(6) . . . . ?
C5 C6 C7 C2 -0.4(5) . . . . ?
C6 N1 C9 C10 179.1(3) . . . . ?
C7 C2 C3 C4 0.0(6) . . . . ?
C8 C4 C5 C6 -177.9(4) . . . . ?
C9 N1 C6 C5 -4.4(6) . . . . ?
C9 N1 C6 C7 176.7(3) . . . . ?
C9 C10 C11 O1 0.3(5) . . . . ?
C9 C10 C11 C12 -179.1(3) . . . . ?
C9 C10 C15 C14 179.2(4) . . . . ?
C10 C11 C12 C13 0.0(5) . . . . ?
C11 C10 C15 C14 -0.1(6) . . . . ?
C11 C12 C13 O2 178.7(3) . . . . ?
C11 C12 C13 C14 -0.4(6) . . . . ?
C12 C13 C14 C15 0.6(6) . . . . ?
C13 C14 C15 C10 -0.3(6) . . . . ?
C15 C10 C11 O1 179.6(3) . . . . ?
C15 C10 C11 C12 0.3(5) . . . . ?
C16 O2 C13 C12 5.8(5) . . . . ?
C16 O2 C13 C14 -175.0(3) . . . . ?

_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 4.300
_oxdiff_exptl_absorpt_empirical_full_min 0.499
####################################################################### 
# 
# 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_r20221019d
_database_code_depnum_ccdc_archive 'CCDC 2235345'
loop_
_audit_author_name
_audit_author_address
MN-II
;Tianjin university
China
;
_audit_update_record             
;
2023-01-10 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;
_audit_creation_date             2022-10-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 F6 N2 O'
_chemical_formula_sum            'C17 H14 F6 N2 O'
_chemical_formula_weight         376.30
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   6.2342(8)
_cell_length_b                   14.8463(18)
_cell_length_c                   18.019(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1667.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3861
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      31.8800
_cell_measurement_theta_min      1.8310
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_av_unetI/netI     0.0797
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13481
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.644
_diffrn_ambient_temperature      294.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00   25.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  35.00   1.00   25.00    --  -25.00  45.00  90.00  150
  3  ω   -115.00   5.00   1.00   25.00    --  -25.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn70'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0072651000
_diffrn_orient_matrix_UB_12      0.0472151000
_diffrn_orient_matrix_UB_13      0.0054025000
_diffrn_orient_matrix_UB_21      -0.0047002000
_diffrn_orient_matrix_UB_22      -0.0066861000
_diffrn_orient_matrix_UB_23      0.0389355000
_diffrn_orient_matrix_UB_31      0.1134992000
_diffrn_orient_matrix_UB_32      0.0026892000
_diffrn_orient_matrix_UB_33      0.0019259000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                1798
_reflns_number_total             3028
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 547 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.1(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3028
_refine_ls_number_restraints     225
_refine_ls_R_factor_all          0.1338
_refine_ls_R_factor_gt           0.0742
_refine_ls_restrained_S_all      1.122
_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)+(0.1002P)²+0.5223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1735
_refine_ls_wR_factor_ref         0.2074
_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. Restrained distances
 F1-C16 \\sim F2-C16 \\sim F3-C16 \\sim F4-C17 \\sim F5-C17 \\sim F6-C17
 with sigma of 0.01
 F1-F2 \\sim F1-F3 \\sim F2-F3 \\sim F4-F5 \\sim F4-F6 \\sim F5-F6 \\sim
F1A-F2A \\sim F1A-F3A \\sim F2A-F3A ~
 F4A-F5A \\sim F4A-F6A \\sim F5A-F6A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim F1A \\sim F2A \\sim F3A
\\sim F4A \\sim F5A \\sim F6A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F4) \\sim
Ueq, Uanis(F5) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F2A)
\\sim Ueq, Uanis(F3A) \\sim Ueq, Uanis(F4A) \\sim Ueq, Uanis(F5A) \\sim Ueq,
Uanis(F6A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C9(H9), C11(H11), C13(H13), C15(H15)
5.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
5.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
O1 O 0.3834(9) 0.6797(3) 0.6671(3) 0.0832(17) Uani 1 1 d . . . . .
H1 H 0.481923 0.664627 0.694619 0.125 Uiso 1 1 calc R U . . .
N1 N -0.1656(9) 0.5556(4) 0.5171(3) 0.0658(16) Uani 1 1 d . . . . .
N2 N 0.6778(9) 0.5711(4) 0.7211(3) 0.0614(15) Uani 1 1 d . . . . .
C1 C -0.2582(14) 0.6426(6) 0.5036(5) 0.088(3) Uani 1 1 d . . . . .
H1A H -0.384506 0.635959 0.473605 0.132 Uiso 1 1 calc R U . . .
H1B H -0.156170 0.679857 0.478087 0.132 Uiso 1 1 calc R U . . .
H1C H -0.295789 0.670099 0.549996 0.132 Uiso 1 1 calc R U . . .
C2 C -0.2708(12) 0.4803(6) 0.4824(4) 0.077(2) Uani 1 1 d . . . . .
H2A H -0.392731 0.501234 0.454855 0.115 Uiso 1 1 calc R U . . .
H2B H -0.317436 0.438641 0.519899 0.115 Uiso 1 1 calc R U . . .
H2C H -0.172560 0.450640 0.449481 0.115 Uiso 1 1 calc R U . . .
C3 C 0.0148(10) 0.5471(5) 0.5573(3) 0.0518(17) Uani 1 1 d . . . . .
C4 C 0.1117(11) 0.6197(5) 0.5924(4) 0.0598(18) Uani 1 1 d . . . . .
H4 H 0.052525 0.676992 0.588051 0.072 Uiso 1 1 calc R U . . .
C5 C 0.3005(11) 0.6068(4) 0.6348(4) 0.0584(19) Uani 1 1 d . . . . .
C6 C 0.3941(11) 0.5217(5) 0.6426(4) 0.0580(18) Uani 1 1 d . . . . .
C7 C 0.2968(11) 0.4492(5) 0.6091(4) 0.0661(19) Uani 1 1 d . . . . .
H7 H 0.355314 0.392003 0.614458 0.079 Uiso 1 1 calc R U . . .
C8 C 0.1138(11) 0.4607(5) 0.5677(4) 0.0620(18) Uani 1 1 d . . . . .
H8 H 0.051694 0.410550 0.545490 0.074 Uiso 1 1 calc R U . . .
C9 C 0.5895(12) 0.5082(5) 0.6859(4) 0.0616(19) Uani 1 1 d . . . . .
H9 H 0.650773 0.451142 0.687363 0.074 Uiso 1 1 calc R U . . .
C10 C 0.8658(9) 0.5554(4) 0.7630(3) 0.0473(15) Uani 1 1 d . . . . .
C11 C 0.9533(11) 0.6308(4) 0.7964(4) 0.0554(17) Uani 1 1 d . . . . .
H11 H 0.886442 0.686344 0.790270 0.066 Uiso 1 1 calc R U . . .
C12 C 1.1364(11) 0.6256(4) 0.8384(3) 0.0516(15) Uani 1 1 d . . . . .
C13 C 1.2382(10) 0.5443(4) 0.8496(3) 0.0487(15) Uani 1 1 d . . . . .
H13 H 1.361921 0.540779 0.878343 0.058 Uiso 1 1 calc R U . . .
C14 C 1.1517(9) 0.4678(4) 0.8171(3) 0.0464(15) Uani 1 1 d . . . . .
C15 C 0.9678(10) 0.4731(4) 0.7745(3) 0.0491(16) Uani 1 1 d . . . . .
H15 H 0.911640 0.421117 0.753230 0.059 Uiso 1 1 calc R U . . .
C16 C 1.2258(13) 0.7080(5) 0.8748(4) 0.082(2) Uani 1 1 d D . . . .
C17 C 1.2640(11) 0.3804(4) 0.8298(4) 0.0642(18) Uani 1 1 d D . . . .
F1 F 1.210(2) 0.7799(8) 0.8332(7) 0.117(4) Uani 0.675(9) 1 d D U P A 1
F2 F 1.118(2) 0.7265(9) 0.9361(6) 0.138(5) Uani 0.675(9) 1 d D U P A 1
F3 F 1.4274(14) 0.7019(7) 0.8958(7) 0.122(4) Uani 0.675(9) 1 d D U P A 1
F4 F 1.2368(19) 0.3228(6) 0.7757(6) 0.123(4) Uani 0.675(9) 1 d D U P A 1
F5 F 1.2098(17) 0.3427(7) 0.8916(6) 0.117(4) Uani 0.675(9) 1 d D U P A 1
F6 F 1.4777(9) 0.3893(5) 0.8342(6) 0.088(3) Uani 0.675(9) 1 d D U P A 1
F1A F 1.120(4) 0.783(2) 0.8568(14) 0.118(8) Uani 0.325(9) 1 d D U P A 2
F2A F 1.238(4) 0.7065(16) 0.9450(9) 0.107(6) Uani 0.325(9) 1 d D U P A 2
F3A F 1.423(3) 0.7222(17) 0.8487(13) 0.125(7) Uani 0.325(9) 1 d D U P A 2
F4A F 1.094(2) 0.3094(9) 0.8306(12) 0.099(5) Uani 0.325(9) 1 d D U P A 2
F5A F 1.328(4) 0.3671(13) 0.8975(10) 0.097(6) Uani 0.325(9) 1 d D U P A 2
F6A F 1.380(3) 0.3536(12) 0.7829(12) 0.105(6) Uani 0.325(9) 1 d D U 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
O1 H1 0.8200 . ?
O1 C5 1.333(7) . ?
N1 C1 1.435(9) . ?
N1 C2 1.439(9) . ?
N1 C3 1.343(8) . ?
N2 C9 1.256(8) . ?
N2 C10 1.412(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.389(9) . ?
C3 C8 1.435(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.416(10) . ?
C5 C6 1.399(9) . ?
C6 C7 1.375(9) . ?
C6 C9 1.461(9) . ?
C7 H7 0.9300 . ?
C7 C8 1.373(10) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.384(9) . ?
C10 C15 1.393(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.371(9) . ?
C12 C13 1.379(9) . ?
C12 C16 1.496(10) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(8) . ?
C14 C15 1.382(8) . ?
C14 C17 1.492(9) . ?
C15 H15 0.9300 . ?
C16 F1 1.308(8) . ?
C16 F2 1.322(8) . ?
C16 F3 1.316(8) . ?
C16 F1A 1.34(2) . ?
C16 F2A 1.268(19) . ?
C16 F3A 1.33(2) . ?
C17 F4 1.309(7) . ?
C17 F5 1.292(8) . ?
C17 F6 1.341(7) . ?
C17 F4A 1.497(13) . ?
C17 F5A 1.299(17) . ?
C17 F6A 1.183(15) . ?

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 H1 109.5 . . ?
C1 N1 C2 116.2(6) . . ?
C3 N1 C1 120.9(6) . . ?
C3 N1 C2 122.8(6) . . ?
C9 N2 C10 120.7(6) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 122.4(7) . . ?
N1 C3 C8 121.0(6) . . ?
C4 C3 C8 116.5(6) . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.1(6) . . ?
C5 C4 H4 119.9 . . ?
O1 C5 C4 116.6(7) . . ?
O1 C5 C6 121.8(6) . . ?
C6 C5 C4 121.5(6) . . ?
C5 C6 C9 121.7(6) . . ?
C7 C6 C5 118.6(6) . . ?
C7 C6 C9 119.7(7) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.5(7) . . ?
C8 C7 H7 119.7 . . ?
C3 C8 H8 118.7 . . ?
C7 C8 C3 122.6(7) . . ?
C7 C8 H8 118.7 . . ?
N2 C9 C6 122.3(6) . . ?
N2 C9 H9 118.9 . . ?
C6 C9 H9 118.9 . . ?
C11 C10 N2 115.2(6) . . ?
C11 C10 C15 117.7(5) . . ?
C15 C10 N2 127.1(6) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.5(6) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C13 120.9(6) . . ?
C11 C12 C16 120.4(6) . . ?
C13 C12 C16 118.7(6) . . ?
C12 C13 H13 120.8 . . ?
C12 C13 C14 118.4(6) . . ?
C14 C13 H13 120.8 . . ?
C13 C14 C17 117.7(5) . . ?
C15 C14 C13 120.8(5) . . ?
C15 C14 C17 121.6(5) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 C10 120.7(6) . . ?
C14 C15 H15 119.6 . . ?
F1 C16 C12 112.9(9) . . ?
F1 C16 F2 105.8(8) . . ?
F1 C16 F3 106.9(8) . . ?
F2 C16 C12 110.3(8) . . ?
F3 C16 C12 115.2(7) . . ?
F3 C16 F2 105.2(8) . . ?
F1A C16 C12 113.2(15) . . ?
F2A C16 C12 116.5(12) . . ?
F2A C16 F1A 106.6(16) . . ?
F2A C16 F3A 107.4(13) . . ?
F3A C16 C12 108.5(12) . . ?
F3A C16 F1A 103.7(14) . . ?
C14 C17 F4A 106.3(7) . . ?
F4 C17 C14 113.2(6) . . ?
F4 C17 F6 103.7(7) . . ?
F5 C17 C14 112.8(7) . . ?
F5 C17 F4 109.0(7) . . ?
F5 C17 F6 104.6(7) . . ?
F6 C17 C14 112.9(6) . . ?
F5A C17 C14 114.9(10) . . ?
F5A C17 F4A 95.9(10) . . ?
F6A C17 C14 118.1(10) . . ?
F6A C17 F4A 101.8(10) . . ?
F6A C17 F5A 115.6(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 C5 C6 C7 178.5(6) . . . . ?
O1 C5 C6 C9 -0.8(10) . . . . ?
N1 C3 C4 C5 179.3(6) . . . . ?
N1 C3 C8 C7 -179.2(6) . . . . ?
N2 C10 C11 C12 -179.7(5) . . . . ?
N2 C10 C15 C14 -179.8(5) . . . . ?
C1 N1 C3 C4 5.0(10) . . . . ?
C1 N1 C3 C8 -176.8(7) . . . . ?
C2 N1 C3 C4 -178.0(6) . . . . ?
C2 N1 C3 C8 0.2(10) . . . . ?
C3 C4 C5 O1 -179.7(6) . . . . ?
C3 C4 C5 C6 0.0(9) . . . . ?
C4 C3 C8 C7 -0.9(10) . . . . ?
C4 C5 C6 C7 -1.1(10) . . . . ?
C4 C5 C6 C9 179.6(6) . . . . ?
C5 C6 C7 C8 1.2(10) . . . . ?
C5 C6 C9 N2 3.5(9) . . . . ?
C6 C7 C8 C3 -0.2(11) . . . . ?
C7 C6 C9 N2 -175.8(7) . . . . ?
C8 C3 C4 C5 1.0(9) . . . . ?
C9 N2 C10 C11 177.1(6) . . . . ?
C9 N2 C10 C15 -3.9(9) . . . . ?
C9 C6 C7 C8 -179.5(6) . . . . ?
C10 N2 C9 C6 179.5(5) . . . . ?
C10 C11 C12 C13 -1.0(10) . . . . ?
C10 C11 C12 C16 -179.1(6) . . . . ?
C11 C10 C15 C14 -0.8(8) . . . . ?
C11 C12 C13 C14 0.3(9) . . . . ?
C11 C12 C16 F1 -38.8(11) . . . . ?
C11 C12 C16 F2 79.3(10) . . . . ?
C11 C12 C16 F3 -161.9(9) . . . . ?
C11 C12 C16 F1A -5.0(16) . . . . ?
C11 C12 C16 F2A 119.2(16) . . . . ?
C11 C12 C16 F3A -119.5(14) . . . . ?
C12 C13 C14 C15 0.0(9) . . . . ?
C12 C13 C14 C17 179.9(6) . . . . ?
C13 C12 C16 F1 143.0(9) . . . . ?
C13 C12 C16 F2 -98.9(9) . . . . ?
C13 C12 C16 F3 19.9(11) . . . . ?
C13 C12 C16 F1A 176.8(14) . . . . ?
C13 C12 C16 F2A -59.0(17) . . . . ?
C13 C12 C16 F3A 62.3(15) . . . . ?
C13 C14 C15 C10 0.2(9) . . . . ?
C13 C14 C17 F4 -151.8(9) . . . . ?
C13 C14 C17 F5 83.9(10) . . . . ?
C13 C14 C17 F6 -34.4(9) . . . . ?
C13 C14 C17 F4A 147.7(10) . . . . ?
C13 C14 C17 F5A 43.0(14) . . . . ?
C13 C14 C17 F6A -98.9(17) . . . . ?
C15 C10 C11 C12 1.2(9) . . . . ?
C15 C14 C17 F4 28.1(10) . . . . ?
C15 C14 C17 F5 -96.2(9) . . . . ?
C15 C14 C17 F6 145.5(7) . . . . ?
C15 C14 C17 F4A -32.4(11) . . . . ?
C15 C14 C17 F5A -137.0(13) . . . . ?
C15 C14 C17 F6A 81.1(16) . . . . ?
C16 C12 C13 C14 178.5(6) . . . . ?
C17 C14 C15 C10 -179.7(6) . . . . ?

_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 1.148
_oxdiff_exptl_absorpt_empirical_full_min 0.897
####################################################################### 
# 
# 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_r20221019c
_database_code_depnum_ccdc_archive 'CCDC 2235342'
loop_
_audit_author_name
_audit_author_address
MN-I
;Tianjin university
China
;
_audit_update_record             
;
2023-01-10 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;
_audit_creation_date             2022-10-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 F6 N2 O'
_chemical_formula_sum            'C17 H14 F6 N2 O'
_chemical_formula_weight         376.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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                   4.9857(8)
_cell_length_b                   10.6861(12)
_cell_length_c                   16.2064(17)
_cell_angle_alpha                78.810(9)
_cell_angle_beta                 83.660(11)
_cell_angle_gamma                88.872(11)
_cell_volume                     841.84(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2147
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      32.6490
_cell_measurement_theta_min      3.8470
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_unetI/netI     0.0952
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8169
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         2.530
_diffrn_ambient_temperature      294.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00   25.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00   25.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00   25.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn70'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0383164000
_diffrn_orient_matrix_UB_12      0.0021071000
_diffrn_orient_matrix_UB_13      0.0431785000
_diffrn_orient_matrix_UB_21      -0.0075495000
_diffrn_orient_matrix_UB_22      0.0674845000
_diffrn_orient_matrix_UB_23      -0.0104582000
_diffrn_orient_matrix_UB_31      -0.1377136000
_diffrn_orient_matrix_UB_32      -0.0044178000
_diffrn_orient_matrix_UB_33      -0.0063699000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1351
_reflns_number_total             3029
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.15(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         3029
_refine_ls_number_restraints     192
_refine_ls_R_factor_all          0.1663
_refine_ls_R_factor_gt           0.0764
_refine_ls_restrained_S_all      1.260
_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)+(0.1039P)²+0.1512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1901
_refine_ls_wR_factor_ref         0.2494
_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. Restrained distances
 F4-C17 \\sim F4A-C17 \\sim F5-C17 \\sim F5A-C17 \\sim F6-C17 \\sim F6A-C17
 with sigma of 0.01
 F4-F5 \\sim F4-F6 \\sim F5-F6 \\sim F4A-F5A \\sim F4A-F6A \\sim F5A-F6A
 with sigma of 0.01
 F1-C16 \\sim F1A-C16 \\sim F2-C16 \\sim F2A-C16 \\sim F3-C16 \\sim F3A-C16
 with sigma of 0.01
 F1-F2 \\sim F1-F3 \\sim F2-F3 \\sim F1-F2 \\sim F1-F3 \\sim F2-F3
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
F4 \\sim F5 \\sim F6 \\sim F1A \\sim F2A \\sim F3A \\sim F4A \\sim F5A \\sim
F6A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim F1A \\sim F2A \\sim F3A:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(F4) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F1A) \\sim
Ueq, Uanis(F2A) \\sim Ueq, Uanis(F3A) \\sim Ueq, Uanis(F4A) \\sim Ueq,
Uanis(F5A) \\sim Ueq, Uanis(F6A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F4) \\sim
Ueq, Uanis(F5) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F2A)
\\sim Ueq, Uanis(F3A) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C9(H9), C11(H11), C13(H13), C15(H15)
5.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
5.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
O1 O 0.4221(6) 0.5528(3) 0.88844(16) 0.0831(9) Uani 1 1 d . . . . .
H1 H 0.319567 0.584349 0.853853 0.125 Uiso 1 1 calc R U . . .
N1 N 1.0694(6) 0.2247(3) 0.9354(2) 0.0766(10) Uani 1 1 d . . . . .
N2 N 0.2069(6) 0.5943(3) 0.74847(17) 0.0635(9) Uani 1 1 d . . . . .
C1 C 1.0980(9) 0.2524(4) 1.0179(3) 0.0915(14) Uani 1 1 d . . . . .
H1A H 0.927119 0.241296 1.052133 0.137 Uiso 1 1 calc R U . . .
H1B H 1.158050 0.338893 1.011749 0.137 Uiso 1 1 calc R U . . .
H1C H 1.227923 0.195470 1.044666 0.137 Uiso 1 1 calc R U . . .
C2 C 1.2279(8) 0.1212(4) 0.9098(3) 0.0908(14) Uani 1 1 d . . . . .
H2A H 1.333089 0.083174 0.954256 0.136 Uiso 1 1 calc R U . . .
H2B H 1.345968 0.153501 0.859538 0.136 Uiso 1 1 calc R U . . .
H2C H 1.109655 0.058170 0.898470 0.136 Uiso 1 1 calc R U . . .
C3 C 0.9020(7) 0.2951(3) 0.8834(2) 0.0593(9) Uani 1 1 d . . . . .
C4 C 0.7446(7) 0.3924(3) 0.9097(2) 0.0614(10) Uani 1 1 d . . . . .
H4 H 0.758499 0.410966 0.962782 0.074 Uiso 1 1 calc R U . . .
C5 C 0.5704(7) 0.4610(3) 0.8588(2) 0.0588(9) Uani 1 1 d . . . . .
C6 C 0.5420(7) 0.4354(3) 0.7782(2) 0.0572(9) Uani 1 1 d . . . . .
C7 C 0.7053(7) 0.3397(3) 0.7520(2) 0.0651(10) Uani 1 1 d . . . . .
H7 H 0.694341 0.322004 0.698525 0.078 Uiso 1 1 calc R U . . .
C8 C 0.8800(7) 0.2713(3) 0.8021(2) 0.0665(11) Uani 1 1 d . . . . .
H8 H 0.985643 0.208337 0.782383 0.080 Uiso 1 1 calc R U . . .
C9 C 0.3564(7) 0.5046(3) 0.7256(2) 0.0625(10) Uani 1 1 d . . . . .
H9 H 0.342717 0.484327 0.672966 0.075 Uiso 1 1 calc R U . . .
C10 C 0.0275(7) 0.6656(3) 0.6974(2) 0.0623(10) Uani 1 1 d . . . . .
C11 C -0.1276(8) 0.7546(3) 0.7326(3) 0.0718(11) Uani 1 1 d . . . . .
H11 H -0.110845 0.760966 0.788190 0.086 Uiso 1 1 calc R U . . .
C12 C -0.3042(8) 0.8333(4) 0.6890(3) 0.0769(12) Uani 1 1 d . . . . .
C13 C -0.3359(9) 0.8255(4) 0.6077(3) 0.0882(13) Uani 1 1 d . . . . .
H13 H -0.454879 0.879408 0.577503 0.106 Uiso 1 1 calc R U . . .
C14 C -0.1864(9) 0.7352(5) 0.5708(3) 0.0876(13) Uani 1 1 d . . . . .
C15 C -0.0060(8) 0.6558(4) 0.6149(2) 0.0778(12) Uani 1 1 d . . . . .
H15 H 0.092532 0.596121 0.589337 0.093 Uiso 1 1 calc R U . . .
C16 C -0.4547(10) 0.9293(5) 0.7315(4) 0.1086(17) Uani 1 1 d D . . . .
C17 C -0.2207(11) 0.7218(5) 0.4833(4) 0.130(2) Uani 1 1 d D . . . .
F1 F -0.6159(14) 0.8735(7) 0.8012(4) 0.108(2) Uani 0.513(6) 1 d D U P A 1
F2 F -0.2987(15) 1.0044(9) 0.7608(8) 0.143(3) Uani 0.513(6) 1 d D U P A 1
F3 F -0.616(2) 0.9998(12) 0.6839(8) 0.177(5) Uani 0.513(6) 1 d D U P A 1
F4 F -0.388(2) 0.8070(8) 0.4485(7) 0.169(4) Uani 0.513(6) 1 d D U P A 1
F5 F -0.357(2) 0.6089(7) 0.4869(4) 0.156(3) Uani 0.513(6) 1 d D U P A 1
F6 F -0.0071(15) 0.7163(13) 0.4347(6) 0.183(4) Uani 0.513(6) 1 d D U P A 1
F1A F -0.463(3) 0.9121(13) 0.8129(5) 0.183(4) Uani 0.487(6) 1 d D U P A 2
F2A F -0.334(2) 1.0420(7) 0.6996(7) 0.144(3) Uani 0.487(6) 1 d D U P A 2
F3A F -0.6928(15) 0.9583(10) 0.7044(8) 0.120(3) Uani 0.487(6) 1 d D U P A 2
F4A F -0.4609(13) 0.7275(12) 0.4612(7) 0.163(4) Uani 0.487(6) 1 d D U P A 2
F5A F -0.086(2) 0.6278(7) 0.4548(5) 0.140(3) Uani 0.487(6) 1 d D U P A 2
F6A F -0.092(2) 0.8262(8) 0.4301(5) 0.174(4) Uani 0.487(6) 1 d D U 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
O1 H1 0.8200 . ?
O1 C5 1.347(4) . ?
N1 C1 1.447(5) . ?
N1 C2 1.447(4) . ?
N1 C3 1.363(4) . ?
N2 C9 1.288(4) . ?
N2 C10 1.399(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.395(4) . ?
C3 C8 1.405(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(5) . ?
C5 C6 1.408(4) . ?
C6 C7 1.396(4) . ?
C6 C9 1.425(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.361(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.382(5) . ?
C10 C15 1.390(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.364(5) . ?
C12 C13 1.362(6) . ?
C12 C16 1.489(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.394(6) . ?
C14 C15 1.384(5) . ?
C14 C17 1.481(7) . ?
C15 H15 0.9300 . ?
C16 F1 1.354(6) . ?
C16 F2 1.314(6) . ?
C16 F3 1.304(7) . ?
C16 F1A 1.291(7) . ?
C16 F2A 1.340(7) . ?
C16 F3A 1.321(6) . ?
C17 F4 1.310(6) . ?
C17 F5 1.384(6) . ?
C17 F6 1.260(6) . ?
C17 F4A 1.285(6) . ?
C17 F5A 1.325(6) . ?
C17 F6A 1.390(6) . ?

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 H1 109.5 . . ?
C1 N1 C2 117.6(3) . . ?
C3 N1 C1 121.1(3) . . ?
C3 N1 C2 121.3(3) . . ?
C9 N2 C10 123.5(3) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 120.8(3) . . ?
N1 C3 C8 121.3(3) . . ?
C4 C3 C8 117.9(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
O1 C5 C4 118.2(3) . . ?
O1 C5 C6 120.5(3) . . ?
C4 C5 C6 121.2(3) . . ?
C5 C6 C9 121.5(3) . . ?
C7 C6 C5 116.9(3) . . ?
C7 C6 C9 121.6(3) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 C6 122.3(3) . . ?
C8 C7 H7 118.9 . . ?
C3 C8 H8 119.7 . . ?
C7 C8 C3 120.5(3) . . ?
C7 C8 H8 119.7 . . ?
N2 C9 C6 122.3(3) . . ?
N2 C9 H9 118.9 . . ?
C6 C9 H9 118.9 . . ?
C11 C10 N2 116.5(3) . . ?
C11 C10 C15 117.5(4) . . ?
C15 C10 N2 126.0(3) . . ?
C10 C11 H11 118.7 . . ?
C12 C11 C10 122.7(4) . . ?
C12 C11 H11 118.7 . . ?
C11 C12 C16 118.5(4) . . ?
C13 C12 C11 120.2(4) . . ?
C13 C12 C16 121.3(4) . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.7(4) . . ?
C14 C13 H13 120.6 . . ?
C13 C14 C17 120.2(4) . . ?
C15 C14 C13 121.0(4) . . ?
C15 C14 C17 118.7(4) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 C10 119.8(4) . . ?
C14 C15 H15 120.1 . . ?
F1 C16 C12 111.9(5) . . ?
F2 C16 C12 113.8(5) . . ?
F2 C16 F1 103.5(6) . . ?
F3 C16 C12 113.3(9) . . ?
F3 C16 F1 104.9(6) . . ?
F3 C16 F2 108.6(6) . . ?
F1A C16 C12 117.2(6) . . ?
F1A C16 F2A 107.3(9) . . ?
F1A C16 F3A 112.7(9) . . ?
F2A C16 C12 106.6(6) . . ?
F3A C16 C12 113.3(6) . . ?
F3A C16 F2A 97.5(7) . . ?
F4 C17 C14 111.7(7) . . ?
F4 C17 F5 102.0(6) . . ?
F5 C17 C14 108.4(5) . . ?
F6 C17 C14 116.3(6) . . ?
F6 C17 F4 111.4(6) . . ?
F6 C17 F5 105.7(6) . . ?
F4A C17 C14 118.1(7) . . ?
F4A C17 F5A 109.8(6) . . ?
F4A C17 F6A 103.4(6) . . ?
F5A C17 C14 116.6(5) . . ?
F5A C17 F6A 100.0(6) . . ?
F6A C17 C14 106.4(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C5 C6 C7 179.3(3) . . . . ?
O1 C5 C6 C9 -0.3(5) . . . . ?
N1 C3 C4 C5 -178.1(3) . . . . ?
N1 C3 C8 C7 177.8(3) . . . . ?
N2 C10 C11 C12 177.8(3) . . . . ?
N2 C10 C15 C14 -178.2(4) . . . . ?
C1 N1 C3 C4 -2.7(5) . . . . ?
C1 N1 C3 C8 177.9(4) . . . . ?
C2 N1 C3 C4 178.2(3) . . . . ?
C2 N1 C3 C8 -1.1(5) . . . . ?
C3 C4 C5 O1 179.3(3) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C4 C3 C8 C7 -1.5(5) . . . . ?
C4 C5 C6 C7 -1.8(5) . . . . ?
C4 C5 C6 C9 178.6(3) . . . . ?
C5 C6 C7 C8 1.6(5) . . . . ?
C5 C6 C9 N2 0.5(5) . . . . ?
C6 C7 C8 C3 0.1(6) . . . . ?
C7 C6 C9 N2 -179.1(3) . . . . ?
C8 C3 C4 C5 1.3(5) . . . . ?
C9 N2 C10 C11 177.1(3) . . . . ?
C9 N2 C10 C15 -3.6(6) . . . . ?
C9 C6 C7 C8 -178.8(3) . . . . ?
C10 N2 C9 C6 178.5(3) . . . . ?
C10 C11 C12 C13 0.7(6) . . . . ?
C10 C11 C12 C16 -177.8(4) . . . . ?
C11 C10 C15 C14 1.1(6) . . . . ?
C11 C12 C13 C14 0.5(6) . . . . ?
C11 C12 C16 F1 -62.1(6) . . . . ?
C11 C12 C16 F2 54.8(8) . . . . ?
C11 C12 C16 F3 179.6(6) . . . . ?
C11 C12 C16 F1A -17.1(12) . . . . ?
C11 C12 C16 F2A 102.9(7) . . . . ?
C11 C12 C16 F3A -151.0(7) . . . . ?
C12 C13 C14 C15 -0.9(7) . . . . ?
C12 C13 C14 C17 178.4(4) . . . . ?
C13 C12 C16 F1 119.4(6) . . . . ?
C13 C12 C16 F2 -123.7(7) . . . . ?
C13 C12 C16 F3 1.1(8) . . . . ?
C13 C12 C16 F1A 164.4(11) . . . . ?
C13 C12 C16 F2A -75.5(7) . . . . ?
C13 C12 C16 F3A 30.5(8) . . . . ?
C13 C14 C15 C10 0.1(6) . . . . ?
C13 C14 C17 F4 3.6(8) . . . . ?
C13 C14 C17 F5 -108.1(6) . . . . ?
C13 C14 C17 F6 133.0(8) . . . . ?
C13 C14 C17 F4A -41.2(9) . . . . ?
C13 C14 C17 F5A -175.3(7) . . . . ?
C13 C14 C17 F6A 74.3(7) . . . . ?
C15 C10 C11 C12 -1.5(6) . . . . ?
C15 C14 C17 F4 -177.0(7) . . . . ?
C15 C14 C17 F5 71.3(7) . . . . ?
C15 C14 C17 F6 -47.6(9) . . . . ?
C15 C14 C17 F4A 138.2(8) . . . . ?
C15 C14 C17 F5A 4.1(8) . . . . ?
C15 C14 C17 F6A -106.3(6) . . . . ?
C16 C12 C13 C14 179.0(4) . . . . ?
C17 C14 C15 C10 -179.3(4) . . . . ?

_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 1.833
_oxdiff_exptl_absorpt_empirical_full_min 0.741
####################################################################### 
# 
# 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_r20220922b
_database_code_depnum_ccdc_archive 'CCDC 2235341'
loop_
_audit_author_name
_audit_author_address
MO-II
;Tianjin university
China
;
_audit_update_record             
;
2023-01-10 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;
_audit_creation_date             2022-09-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 F6 N O2'
_chemical_formula_sum            'C16 H11 F6 N O2'
_chemical_formula_weight         363.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   7.4706(6)
_cell_length_b                   30.0542(15)
_cell_length_c                   7.4459(7)
_cell_angle_alpha                90
_cell_angle_beta                 117.037(12)
_cell_angle_gamma                90
_cell_volume                     1489.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5301
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      31.8850
_cell_measurement_theta_min      2.6900
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.711
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00  60.00   1.00    8.00    --  -30.00  45.00   0.00  180
  2  ω   -120.00  30.00   1.00    8.00    --  -30.00  45.00  90.00  150
  3  ω   -120.00   0.00   1.00    8.00    --  -30.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn70'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0495517000
_diffrn_orient_matrix_UB_12      0.0208222000
_diffrn_orient_matrix_UB_13      0.0157043000
_diffrn_orient_matrix_UB_21      -0.0943286000
_diffrn_orient_matrix_UB_22      0.0109966000
_diffrn_orient_matrix_UB_23      -0.0431622000
_diffrn_orient_matrix_UB_31      0.0035303000
_diffrn_orient_matrix_UB_32      0.0015435000
_diffrn_orient_matrix_UB_33      0.0966105000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2203
_reflns_number_total             3033
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0077(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3033
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.048
_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)+(0.0630P)²+0.5544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1492
_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:
 C4(H4), C6(H6), C8(H8), C9(H9), C12(H12), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 -0.1421(3) 0.61250(7) -0.0538(3) 0.0685(6) Uani 1 1 d . . . . .
F2 F -0.0139(3) 0.54816(6) -0.0173(3) 0.0663(6) Uani 1 1 d . . . . .
F3 F 0.1279(3) 0.60302(8) -0.0778(3) 0.0658(6) Uani 1 1 d . . . . .
F4 F 0.2130(2) 0.51582(5) 0.7229(2) 0.0424(4) Uani 1 1 d . . . . .
F5 F 0.4898(3) 0.50773(5) 0.7072(3) 0.0506(5) Uani 1 1 d . . . . .
F6 F 0.4755(3) 0.55147(5) 0.9279(2) 0.0493(5) Uani 1 1 d . . . . .
O1 O 0.3403(2) 0.78436(5) 0.5194(3) 0.0299(4) Uani 1 1 d . . . . .
H1 H 0.307828 0.757404 0.497608 0.045 Uiso 1 1 calc R U . . .
O2 O 0.8710(2) 0.87498(5) 0.9901(3) 0.0288(4) Uani 1 1 d . . . . .
N1 N 0.3901(3) 0.69762(6) 0.5631(3) 0.0246(5) Uani 1 1 d . . . . .
C1 C 0.0312(4) 0.59061(8) 0.0257(4) 0.0311(6) Uani 1 1 d . . . . .
C2 C 0.3740(4) 0.53802(8) 0.7370(4) 0.0317(6) Uani 1 1 d . . . . .
C3 C 0.1514(3) 0.59974(8) 0.2458(4) 0.0236(5) Uani 1 1 d . . . . .
C4 C 0.2054(3) 0.56537(8) 0.3846(4) 0.0259(5) Uani 1 1 d . . . . .
H4 H 0.166608 0.535591 0.341777 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3182(3) 0.57547(8) 0.5889(4) 0.0238(5) Uani 1 1 d . . . . .
C6 C 0.3784(3) 0.61872(8) 0.6522(4) 0.0242(5) Uani 1 1 d . . . . .
H6 H 0.453333 0.625092 0.791841 0.029 Uiso 1 1 calc R U . . .
C7 C 0.3286(3) 0.65316(8) 0.5098(4) 0.0228(5) Uani 1 1 d . . . . .
C8 C 0.2103(3) 0.64320(8) 0.3071(4) 0.0236(5) Uani 1 1 d . . . . .
H8 H 0.169500 0.666369 0.209726 0.028 Uiso 1 1 calc R U . . .
C9 C 0.5636(3) 0.70551(8) 0.7118(4) 0.0247(5) Uani 1 1 d . . . . .
H9 H 0.646905 0.681020 0.780818 0.030 Uiso 1 1 calc R U . . .
C10 C 0.6369(3) 0.74992(8) 0.7781(4) 0.0237(5) Uani 1 1 d . . . . .
C11 C 0.5261(3) 0.78780(8) 0.6781(4) 0.0234(5) Uani 1 1 d . . . . .
C12 C 0.6022(3) 0.83022(8) 0.7419(4) 0.0235(5) Uani 1 1 d . . . . .
H12 H 0.528494 0.855687 0.671198 0.028 Uiso 1 1 calc R U . . .
C13 C 0.7872(3) 0.83496(8) 0.9098(4) 0.0230(5) Uani 1 1 d . . . . .
C14 C 0.9025(4) 0.79793(8) 1.0107(4) 0.0271(6) Uani 1 1 d . . . . .
H14 H 1.030262 0.801581 1.124003 0.033 Uiso 1 1 calc R U . . .
C15 C 0.8276(3) 0.75623(8) 0.9426(4) 0.0262(6) Uani 1 1 d . . . . .
H15 H 0.906561 0.730945 1.008363 0.031 Uiso 1 1 calc R U . . .
C16 C 0.7531(4) 0.91413(8) 0.9127(4) 0.0341(6) Uani 1 1 d . . . . .
H16A H 0.728137 0.918854 0.773046 0.051 Uiso 1 1 calc R U . . .
H16B H 0.825454 0.939792 0.994879 0.051 Uiso 1 1 calc R U . . .
H16C H 0.624710 0.910666 0.917079 0.051 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 C1 1.328(3) . ?
F2 C1 1.321(3) . ?
F3 C1 1.327(3) . ?
F4 C2 1.337(3) . ?
F5 C2 1.342(3) . ?
F6 C2 1.334(3) . ?
O1 H1 0.8400 . ?
O1 C11 1.357(3) . ?
O2 C13 1.362(3) . ?
O2 C16 1.425(3) . ?
N1 C7 1.410(3) . ?
N1 C9 1.287(3) . ?
C1 C3 1.493(4) . ?
C2 C5 1.496(3) . ?
C3 C4 1.385(3) . ?
C3 C8 1.388(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.397(3) . ?
C5 C6 1.386(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.405(3) . ?
C7 C8 1.391(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.442(3) . ?
C10 C11 1.405(3) . ?
C10 C15 1.407(3) . ?
C11 C12 1.389(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(3) . ?
C13 C14 1.399(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.372(3) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C11 O1 H1 109.5 . . ?
C13 O2 C16 118.36(19) . . ?
C9 N1 C7 119.2(2) . . ?
F1 C1 C3 112.1(2) . . ?
F2 C1 F1 106.3(2) . . ?
F2 C1 F3 106.1(2) . . ?
F2 C1 C3 113.8(2) . . ?
F3 C1 F1 106.2(2) . . ?
F3 C1 C3 111.8(2) . . ?
F4 C2 F5 105.8(2) . . ?
F4 C2 C5 112.2(2) . . ?
F5 C2 C5 111.9(2) . . ?
F6 C2 F4 106.8(2) . . ?
F6 C2 F5 106.6(2) . . ?
F6 C2 C5 113.0(2) . . ?
C4 C3 C1 120.5(2) . . ?
C4 C3 C8 121.0(2) . . ?
C8 C3 C1 118.5(2) . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.5(2) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C2 117.9(2) . . ?
C6 C5 C2 121.1(2) . . ?
C6 C5 C4 121.1(2) . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0(2) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 N1 123.0(2) . . ?
C8 C7 N1 118.3(2) . . ?
C8 C7 C6 118.7(2) . . ?
C3 C8 C7 120.6(2) . . ?
C3 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
N1 C9 H9 118.6 . . ?
N1 C9 C10 122.8(2) . . ?
C10 C9 H9 118.6 . . ?
C11 C10 C9 121.9(2) . . ?
C11 C10 C15 118.1(2) . . ?
C15 C10 C9 120.0(2) . . ?
O1 C11 C10 121.5(2) . . ?
O1 C11 C12 117.7(2) . . ?
C12 C11 C10 120.8(2) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.2(2) . . ?
C13 C12 H12 120.4 . . ?
O2 C13 C12 123.9(2) . . ?
O2 C13 C14 114.7(2) . . ?
C12 C13 C14 121.4(2) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 C13 118.7(2) . . ?
C15 C14 H14 120.7 . . ?
C10 C15 H15 119.1 . . ?
C14 C15 C10 121.8(2) . . ?
C14 C15 H15 119.1 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 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 C1 C3 C4 120.5(3) . . . . ?
F1 C1 C3 C8 -60.6(3) . . . . ?
F2 C1 C3 C4 -0.1(3) . . . . ?
F2 C1 C3 C8 178.7(2) . . . . ?
F3 C1 C3 C4 -120.3(3) . . . . ?
F3 C1 C3 C8 58.6(3) . . . . ?
F4 C2 C5 C4 -56.9(3) . . . . ?
F4 C2 C5 C6 123.8(2) . . . . ?
F5 C2 C5 C4 61.9(3) . . . . ?
F5 C2 C5 C6 -117.4(2) . . . . ?
F6 C2 C5 C4 -177.8(2) . . . . ?
F6 C2 C5 C6 2.9(3) . . . . ?
O1 C11 C12 C13 176.7(2) . . . . ?
O2 C13 C14 C15 178.6(2) . . . . ?
N1 C7 C8 C3 177.8(2) . . . . ?
N1 C9 C10 C11 -2.8(4) . . . . ?
N1 C9 C10 C15 179.6(2) . . . . ?
C1 C3 C4 C5 179.9(2) . . . . ?
C1 C3 C8 C7 -177.6(2) . . . . ?
C2 C5 C6 C7 178.3(2) . . . . ?
C3 C4 C5 C2 179.5(2) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C3 C8 C7 1.2(3) . . . . ?
C4 C5 C6 C7 -1.0(3) . . . . ?
C5 C6 C7 N1 -178.0(2) . . . . ?
C5 C6 C7 C8 3.2(3) . . . . ?
C6 C7 C8 C3 -3.3(3) . . . . ?
C7 N1 C9 C10 -179.1(2) . . . . ?
C8 C3 C4 C5 1.0(3) . . . . ?
C9 N1 C7 C6 35.3(3) . . . . ?
C9 N1 C7 C8 -145.8(2) . . . . ?
C9 C10 C11 O1 3.0(4) . . . . ?
C9 C10 C11 C12 -178.4(2) . . . . ?
C9 C10 C15 C14 -179.8(2) . . . . ?
C10 C11 C12 C13 -1.9(3) . . . . ?
C11 C10 C15 C14 2.5(4) . . . . ?
C11 C12 C13 O2 -176.9(2) . . . . ?
C11 C12 C13 C14 3.0(4) . . . . ?
C12 C13 C14 C15 -1.3(4) . . . . ?
C13 C14 C15 C10 -1.5(4) . . . . ?
C15 C10 C11 O1 -179.4(2) . . . . ?
C15 C10 C11 C12 -0.8(3) . . . . ?
C16 O2 C13 C12 7.7(3) . . . . ?
C16 O2 C13 C14 -172.2(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 3.705
_oxdiff_exptl_absorpt_empirical_full_min 0.490
