# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_47p
_database_code_depnum_ccdc_archive 'CCDC 1918627'
loop_
_audit_author_name
_audit_author_address
'Yubing Huang'
;Wuyi University
China
;
_audit_update_record             
;
2019-05-25 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;
_audit_creation_date             2018-07-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H4 F8 N2 O'
_chemical_formula_sum            'C12 H4 F8 N2 O'
_chemical_formula_weight         344.17
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   14.0204(10)
_cell_length_b                   7.9073(5)
_cell_length_c                   22.6326(16)
_cell_angle_alpha                90
_cell_angle_beta                 103.220(7)
_cell_angle_gamma                90
_cell_volume                     2442.6(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2181
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.3370
_cell_measurement_theta_min      2.9700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61700
_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    1.872
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_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  0.0235
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4381
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.737
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  65.00   1.00    4.50    --  -11.59  19.00-180.00  117
  2  ω    -81.00 -31.00   1.00    4.50    --  -11.59 -57.00  30.00   50
;
_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      -0.0273951000
_diffrn_orient_matrix_UB_12      -0.0469103000
_diffrn_orient_matrix_UB_13      0.0171398000
_diffrn_orient_matrix_UB_21      0.0348456000
_diffrn_orient_matrix_UB_22      0.0204567000
_diffrn_orient_matrix_UB_23      0.0270649000
_diffrn_orient_matrix_UB_31      -0.0271200000
_diffrn_orient_matrix_UB_32      0.0735886000
_diffrn_orient_matrix_UB_33      0.0033920000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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                1791
_reflns_number_total             2121
_reflns_odcompleteness_completeness 98.70
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.051
_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     208
_refine_ls_number_reflns         2121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0448P)²+0.8038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0912
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C4(H4), C2(H2), C8(H8)
;
_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
F4 F 0.56840(7) 0.36367(13) 0.83604(5) 0.0231(3) Uani 1 1 d . . . . .
F6 F 0.30177(8) 0.37205(15) 0.56536(5) 0.0316(3) Uani 1 1 d . . . . .
F5 F 0.70082(8) 0.63022(15) 0.67661(5) 0.0314(3) Uani 1 1 d . . . . .
F7 F 0.38500(8) 0.53025(15) 0.51820(5) 0.0312(3) Uani 1 1 d . . . . .
F3 F 0.26526(8) 0.74049(16) 0.92208(5) 0.0339(3) Uani 1 1 d . . . . .
F1 F 0.37861(8) 0.59456(17) 0.97953(5) 0.0364(3) Uani 1 1 d . . . . .
F8 F 0.42668(9) 0.27220(16) 0.53643(5) 0.0387(3) Uani 1 1 d . . . . .
F2 F 0.24787(9) 0.47354(17) 0.92912(6) 0.0419(4) Uani 1 1 d . . . . .
O1 O 0.62605(9) 0.63718(17) 0.77723(6) 0.0234(3) Uani 1 1 d . . . . .
N2 N 0.48319(10) 0.51472(19) 0.72456(6) 0.0162(3) Uani 1 1 d . . . . .
N1 N 0.35777(10) 0.6137(2) 0.76912(7) 0.0184(4) Uani 1 1 d . . . . .
C1 C 0.48728(12) 0.4575(2) 0.83184(8) 0.0172(4) Uani 1 1 d . . . . .
C9 C 0.45703(13) 0.4609(2) 0.61914(8) 0.0182(4) Uani 1 1 d . . . . .
C6 C 0.57862(13) 0.5784(2) 0.72965(8) 0.0181(4) Uani 1 1 d . . . . .
C10 C 0.42364(13) 0.4626(2) 0.67042(8) 0.0173(4) Uani 1 1 d . . . . .
H10 H 0.359807 0.428243 0.669292 0.021 Uiso 1 1 calc R . . . .
C3 C 0.36110(13) 0.5673(2) 0.87390(8) 0.0177(4) Uani 1 1 d . . . . .
C5 C 0.44158(12) 0.5290(2) 0.77664(8) 0.0166(4) Uani 1 1 d . . . . .
C4 C 0.31722(13) 0.6301(2) 0.81672(8) 0.0185(4) Uani 1 1 d . . . . .
H4 H 0.257370 0.685502 0.811468 0.022 Uiso 1 1 calc R . . . .
C2 C 0.44808(13) 0.4780(2) 0.88168(8) 0.0195(4) Uani 1 1 d . . . . .
H2 H 0.478776 0.433566 0.919272 0.023 Uiso 1 1 calc R . . . .
C8 C 0.55433(14) 0.5156(2) 0.62026(8) 0.0220(4) Uani 1 1 d . . . . .
H8 H 0.578502 0.513884 0.585271 0.026 Uiso 1 1 calc R . . . .
C7 C 0.61010(13) 0.5696(2) 0.67327(9) 0.0209(4) Uani 1 1 d . . . . .
C11 C 0.39227(14) 0.4088(3) 0.56037(8) 0.0230(5) Uani 1 1 d . . . . .
C12 C 0.31295(14) 0.5938(3) 0.92612(8) 0.0235(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F4 C1 1.343(2) . ?
F6 C11 1.331(2) . ?
F5 C7 1.345(2) . ?
F7 C11 1.341(2) . ?
F3 C12 1.332(2) . ?
F1 C12 1.342(2) . ?
F8 C11 1.346(2) . ?
F2 C12 1.330(2) . ?
O1 C6 1.221(2) . ?
N2 C6 1.410(2) . ?
N2 C10 1.379(2) . ?
N2 C5 1.434(2) . ?
N1 C5 1.329(2) . ?
N1 C4 1.334(2) . ?
C1 C5 1.387(2) . ?
C1 C2 1.373(3) . ?
C9 C10 1.347(2) . ?
C9 C8 1.426(3) . ?
C9 C11 1.487(3) . ?
C6 C7 1.444(3) . ?
C3 C4 1.391(3) . ?
C3 C2 1.385(3) . ?
C3 C12 1.504(3) . ?
C8 C7 1.343(3) . ?

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
C6 N2 C5 117.50(14) . . ?
C10 N2 C6 123.37(15) . . ?
C10 N2 C5 118.46(14) . . ?
C5 N1 C4 118.22(15) . . ?
F4 C1 C5 119.88(16) . . ?
F4 C1 C2 119.92(15) . . ?
C2 C1 C5 120.17(17) . . ?
C10 C9 C8 120.08(16) . . ?
C10 C9 C11 120.80(17) . . ?
C8 C9 C11 119.07(16) . . ?
O1 C6 N2 121.56(17) . . ?
O1 C6 C7 125.66(17) . . ?
N2 C6 C7 112.75(15) . . ?
C9 C10 N2 120.64(16) . . ?
C4 C3 C12 119.93(16) . . ?
C2 C3 C4 119.29(17) . . ?
C2 C3 C12 120.76(16) . . ?
N1 C5 N2 116.63(15) . . ?
N1 C5 C1 122.24(17) . . ?
C1 C5 N2 121.14(16) . . ?
N1 C4 C3 122.48(17) . . ?
C1 C2 C3 117.52(16) . . ?
C7 C8 C9 118.13(17) . . ?
F5 C7 C6 114.16(16) . . ?
F5 C7 C8 120.89(17) . . ?
C8 C7 C6 124.85(17) . . ?
F6 C11 F7 107.32(15) . . ?
F6 C11 F8 107.17(16) . . ?
F6 C11 C9 112.54(15) . . ?
F7 C11 F8 105.30(15) . . ?
F7 C11 C9 111.69(16) . . ?
F8 C11 C9 112.37(15) . . ?
F3 C12 F1 106.74(16) . . ?
F3 C12 C3 112.08(16) . . ?
F1 C12 C3 111.72(15) . . ?
F2 C12 F3 106.65(16) . . ?
F2 C12 F1 107.14(16) . . ?
F2 C12 C3 112.15(16) . . ?


_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 1.621
_oxdiff_exptl_absorpt_empirical_full_min 0.521
####################################################################### 
# 
# 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_cf126
_database_code_depnum_ccdc_archive 'CCDC 1918628'
loop_
_audit_author_name
_audit_author_address
'Yubing Huang'
;Wuyi University
China
;
_audit_update_record             
;
2019-05-25 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;
_audit_creation_date             2018-12-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H6 F6 N2 O'
_chemical_formula_sum            'C12 H6 F6 N2 O'
_chemical_formula_weight         308.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           15
_space_group_name_H-M_alt        'C 1 2/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'
'-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                   10.9802(18)
_cell_length_b                   11.6601(11)
_cell_length_c                   10.2792(18)
_cell_angle_alpha                90
_cell_angle_beta                 114.43(2)
_cell_angle_gamma                90
_cell_volume                     1198.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1008
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      27.6920
_cell_measurement_theta_min      2.6930
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57060
_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    1.708
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.14
_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  0.0280
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2098
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.977
_diffrn_reflns_theta_max         24.977
_diffrn_reflns_theta_min         2.684
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  28.00   1.00    3.50    --  -11.59 -99.00  90.00   34
  2  ω    -42.00  21.00   1.00    3.50    --   11.74 -57.00-150.00   63
  3  ω     -5.00  70.00   1.00    3.50    --   11.74  19.00   0.00   75
;
_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      -0.0490307000
_diffrn_orient_matrix_UB_12      0.0326958000
_diffrn_orient_matrix_UB_13      0.0115530000
_diffrn_orient_matrix_UB_21      0.0394598000
_diffrn_orient_matrix_UB_22      0.0500789000
_diffrn_orient_matrix_UB_23      0.0093856000
_diffrn_orient_matrix_UB_31      -0.0324639000
_diffrn_orient_matrix_UB_32      0.0113999000
_diffrn_orient_matrix_UB_33      -0.0743719000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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                921
_reflns_number_total             1055
_reflns_odcompleteness_completeness 98.84
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1055
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.017
_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)+(0.0622P)²+0.2416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1073
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C3(H3)
;
_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 0.46370(10) 0.12076(8) 0.43121(10) 0.0334(3) Uani 1 1 d . . . . .
F3 F 0.58234(11) 0.12992(9) 0.65808(10) 0.0358(3) Uani 1 1 d . . . . .
F2 F 0.39696(10) 0.22242(9) 0.56297(11) 0.0382(4) Uani 1 1 d . . . . .
O1 O 0.500000 0.50165(14) 0.250000 0.0292(4) Uani 1 2 d S T P . .
N1 N 0.51049(14) 0.34885(12) 0.39750(14) 0.0223(4) Uani 1 1 d . . . . .
C5 C 0.57810(17) 0.29475(14) 0.52234(16) 0.0221(4) Uani 1 1 d . . . . .
C1 C 0.56841(17) 0.44067(15) 0.37459(17) 0.0229(4) Uani 1 1 d . . . . .
C6 C 0.50610(18) 0.19217(15) 0.54356(17) 0.0259(4) Uani 1 1 d . . . . .
C2 C 0.68972(18) 0.48551(16) 0.46961(18) 0.0293(5) Uani 1 1 d . . . . .
H2 H 0.725061 0.551716 0.448302 0.035 Uiso 1 1 calc R . . . .
C4 C 0.70023(18) 0.32939(16) 0.62465(18) 0.0276(4) Uani 1 1 d . . . . .
H4 H 0.743628 0.288329 0.708895 0.033 Uiso 1 1 calc R . . . .
C3 C 0.75559(18) 0.42822(17) 0.5965(2) 0.0327(5) Uani 1 1 d . . . . .
H3 H 0.837029 0.455604 0.663230 0.039 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C6 1.3413(19) . ?
F3 C6 1.3411(19) . ?
F2 C6 1.341(2) . ?
O1 C1 1.3836(18) 2_655 ?
O1 C1 1.3836(18) . ?
N1 C5 1.345(2) . ?
N1 C1 1.315(2) . ?
C5 C6 1.499(3) . ?
C5 C4 1.379(2) . ?
C1 C2 1.388(2) . ?
C2 C3 1.375(3) . ?
C4 C3 1.388(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C1 118.15(17) 2_655 . ?
C1 N1 C5 115.83(14) . . ?
N1 C5 C6 113.39(14) . . ?
N1 C5 C4 124.72(16) . . ?
C4 C5 C6 121.87(16) . . ?
O1 C1 C2 116.97(15) . . ?
N1 C1 O1 117.80(14) . . ?
N1 C1 C2 125.11(15) . . ?
F1 C6 F2 106.15(13) . . ?
F1 C6 C5 112.73(13) . . ?
F3 C6 F1 106.75(14) . . ?
F3 C6 F2 106.48(13) . . ?
F3 C6 C5 112.60(14) . . ?
F2 C6 C5 111.68(14) . . ?
C3 C2 C1 117.39(16) . . ?
C5 C4 C3 117.11(17) . . ?
C2 C3 C4 119.82(16) . . ?


_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 1.583
_oxdiff_exptl_absorpt_empirical_full_min 0.666
