# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_t
_audit_block_doi                 10.5517/ccdc.csd.cc27xfzl
_database_code_depnum_ccdc_archive 'CCDC 2082920'
loop_
_audit_author_name
_audit_author_address
'Hua-Wei Liu'
;Soochow University
China
;
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2021-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 N2 O3'
_chemical_formula_sum            'C22 H20 N2 O3'
_chemical_formula_weight         360.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   25.6297(8)
_cell_length_b                   6.39261(18)
_cell_length_c                   12.4690(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.818(3)
_cell_angle_gamma                90
_cell_volume                     1854.25(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4992
_cell_measurement_theta_min      3.7890
_cell_measurement_theta_max      77.1110

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.701
_shelx_estimated_absorpt_T_min   0.767
_shelx_estimated_absorpt_T_max   0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85997
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12743
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.800
_diffrn_reflns_theta_max         77.285
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             3720
_reflns_number_gt                3422
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_max     0.874
_reflns_Friedel_fraction_full    0.898

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+1.3788P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1305 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3720
_refine_ls_number_parameters     248
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1455
_refine_ls_wR_factor_gt          0.1382
_refine_ls_goodness_of_fit_ref   0.894
_refine_ls_restrained_S_all      0.894
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.37796(12) 1.2920(4) 0.7621(2) 0.0434(6) Uani 1 1 d . . . . .
O2 O 0.54667(13) 0.4835(5) 0.8515(2) 0.0533(8) Uani 1 1 d . . . . .
O3 O 0.57973(10) 0.4482(4) 0.5747(2) 0.0400(6) Uani 1 1 d . . . . .
C1 C 0.40298(13) 1.1126(5) 0.7493(3) 0.0307(6) Uani 1 1 d . . . . .
C2 C 0.38889(13) 1.0473(5) 0.6336(3) 0.0322(6) Uani 1 1 d . . . . .
H2 H 0.363210 1.126890 0.569969 0.039 Uiso 1 1 calc R U . . .
C3 C 0.41237(13) 0.8666(5) 0.6120(3) 0.0302(6) Uani 1 1 d . . . . .
H3 H 0.402383 0.824824 0.533516 0.036 Uiso 1 1 calc R U . . .
C4 C 0.45068(12) 0.7449(5) 0.7044(3) 0.0279(6) Uani 1 1 d . . . . .
C5 C 0.46463(14) 0.8103(6) 0.8199(3) 0.0339(7) Uani 1 1 d . . . . .
H5 H 0.490532 0.731264 0.883580 0.041 Uiso 1 1 calc R U . . .
C6 C 0.44069(14) 0.9907(6) 0.8419(3) 0.0353(7) Uani 1 1 d . . . . .
H6 H 0.450039 1.031173 0.920268 0.042 Uiso 1 1 calc R U . . .
C22 C 0.39779(18) 1.3745(6) 0.8785(4) 0.0467(9) Uani 1 1 d . . . . .
H22A H 0.385956 1.282991 0.926303 0.070 Uiso 1 1 calc R U . . .
H22B H 0.381522 1.512608 0.875449 0.070 Uiso 1 1 calc R U . . .
H22C H 0.439394 1.384221 0.913200 0.070 Uiso 1 1 calc R U . . .
N1 N 0.47277(11) 0.5619(4) 0.6756(2) 0.0304(5) Uani 1 1 d . . . . .
C7 C 0.51742(13) 0.4454(5) 0.7483(3) 0.0296(6) Uani 1 1 d . . . . .
C8 C 0.52868(12) 0.2480(5) 0.6917(3) 0.0291(6) Uani 1 1 d . . . . .
H8A H 0.515043 0.125328 0.719647 0.035 Uiso 1 1 calc R U . . .
H8B H 0.507033 0.256098 0.605740 0.035 Uiso 1 1 calc R U . . .
N2 N 0.59022(10) 0.2229(4) 0.7207(2) 0.0284(5) Uani 1 1 d . . . . .
C9 C 0.62598(13) 0.1291(5) 0.8322(3) 0.0292(6) Uani 1 1 d . . . . .
C10 C 0.61350(15) -0.0718(6) 0.8568(3) 0.0400(8) Uani 1 1 d . . . . .
H10 H 0.582357 -0.146075 0.800599 0.048 Uiso 1 1 calc R U . . .
C11 C 0.64737(19) -0.1618(8) 0.9648(4) 0.0541(11) Uani 1 1 d . . . . .
H11 H 0.638879 -0.297336 0.982016 0.065 Uiso 1 1 calc R U . . .
C12 C 0.69352(19) -0.0545(9) 1.0476(3) 0.0571(12) Uani 1 1 d . . . . .
H12 H 0.716205 -0.116672 1.120783 0.068 Uiso 1 1 calc R U . . .
C13 C 0.70615(16) 0.1444(8) 1.0223(3) 0.0479(10) Uani 1 1 d . . . . .
H13 H 0.738025 0.216426 1.077792 0.057 Uiso 1 1 calc R U . . .
C14 C 0.67185(13) 0.2390(6) 0.9148(3) 0.0353(7) Uani 1 1 d . . . . .
H14 H 0.679777 0.376035 0.898606 0.042 Uiso 1 1 calc R U . . .
C15 C 0.61075(13) 0.3250(5) 0.6507(2) 0.0281(6) Uani 1 1 d . . . . .
C16 C 0.66996(13) 0.2765(5) 0.6600(2) 0.0293(6) Uani 1 1 d . . . . .
C17 C 0.69830(15) 0.4333(6) 0.6283(3) 0.0363(7) Uani 1 1 d . . . . .
H17 H 0.681751 0.567111 0.608981 0.044 Uiso 1 1 calc R U . . .
C18 C 0.75090(16) 0.3941(7) 0.6248(3) 0.0455(9) Uani 1 1 d . . . . .
H18 H 0.769957 0.501196 0.603819 0.055 Uiso 1 1 calc R U . . .
C19 C 0.77497(16) 0.1981(7) 0.6523(3) 0.0455(9) Uani 1 1 d . . . . .
H19 H 0.810691 0.171625 0.650573 0.055 Uiso 1 1 calc R U . . .
C20 C 0.74680(16) 0.0398(7) 0.6824(3) 0.0430(8) Uani 1 1 d . . . . .
H20 H 0.763232 -0.094374 0.699892 0.052 Uiso 1 1 calc R U . . .
C21 C 0.69448(14) 0.0777(6) 0.6871(3) 0.0342(7) Uani 1 1 d . . . . .
H21 H 0.675667 -0.029949 0.708321 0.041 Uiso 1 1 calc R U . . .
H1 H 0.457(2) 0.522(7) 0.602(4) 0.041 Uiso 1 1 d . 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
O1 C1 1.356(4) . ?
O1 C22 1.423(5) . ?
O2 C7 1.211(4) . ?
O3 C15 1.233(4) . ?
C1 C6 1.392(5) . ?
C1 C2 1.396(4) . ?
C2 C3 1.380(5) . ?
C2 H2 0.9400 . ?
C3 C4 1.396(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.394(4) . ?
C4 N1 1.410(4) . ?
C5 C6 1.386(5) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
N1 C7 1.347(4) . ?
N1 H1 0.87(5) . ?
C7 C8 1.532(4) . ?
C8 N2 1.471(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
N2 C15 1.360(4) . ?
N2 C9 1.436(4) . ?
C9 C14 1.386(5) . ?
C9 C10 1.389(5) . ?
C10 C11 1.384(5) . ?
C10 H10 0.9400 . ?
C11 C12 1.382(7) . ?
C11 H11 0.9400 . ?
C12 C13 1.381(7) . ?
C12 H12 0.9400 . ?
C13 C14 1.395(5) . ?
C13 H13 0.9400 . ?
C14 H14 0.9400 . ?
C15 C16 1.505(4) . ?
C16 C17 1.389(5) . ?
C16 C21 1.395(5) . ?
C17 C18 1.389(5) . ?
C17 H17 0.9400 . ?
C18 C19 1.375(6) . ?
C18 H18 0.9400 . ?
C19 C20 1.384(6) . ?
C19 H19 0.9400 . ?
C20 C21 1.388(5) . ?
C20 H20 0.9400 . ?
C21 H21 0.9400 . ?

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 C22 116.7(3) . . ?
O1 C1 C6 125.1(3) . . ?
O1 C1 C2 116.4(3) . . ?
C6 C1 C2 118.5(3) . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.2(3) . . ?
C5 C4 N1 123.7(3) . . ?
C3 C4 N1 118.1(3) . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 120.9(3) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C7 N1 C4 127.3(3) . . ?
C7 N1 H1 116(3) . . ?
C4 N1 H1 117(3) . . ?
O2 C7 N1 125.1(3) . . ?
O2 C7 C8 120.2(3) . . ?
N1 C7 C8 114.6(3) . . ?
N2 C8 C7 111.5(2) . . ?
N2 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
N2 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C15 N2 C9 124.0(2) . . ?
C15 N2 C8 117.0(2) . . ?
C9 N2 C8 117.8(2) . . ?
C14 C9 C10 120.5(3) . . ?
C14 C9 N2 120.4(3) . . ?
C10 C9 N2 119.2(3) . . ?
C11 C10 C9 119.4(4) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 120.7(4) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.3(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 119.4(4) . . ?
C9 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
O3 C15 N2 120.1(3) . . ?
O3 C15 C16 119.6(3) . . ?
N2 C15 C16 120.1(3) . . ?
C17 C16 C21 119.3(3) . . ?
C17 C16 C15 117.4(3) . . ?
C21 C16 C15 122.9(3) . . ?
C16 C17 C18 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.2(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C21 120.5(4) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 119.6(3) . . ?
C20 C21 H21 120.2 . . ?
C16 C21 H21 120.2 . . ?

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.065



####################################################################### 
# 
# 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_g200818a
_audit_block_doi                 10.5517/ccdc.csd.cc277lz2
_database_code_depnum_ccdc_archive 'CCDC 2062894'
loop_
_audit_author_name
_audit_author_address
'Huawei Liu'
;Soochow University
China
;
_audit_update_record             
;
2021-02-13 deposited with the CCDC.	2021-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 F3 N O3'
_chemical_formula_sum            'C14 H15 F3 N O3'
_chemical_formula_weight         302.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   14.5103(9)
_cell_length_b                   10.8097(7)
_cell_length_c                   9.4091(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.534(6)
_cell_angle_gamma                90
_cell_volume                     1473.03(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2955
_cell_measurement_theta_min      4.0330
_cell_measurement_theta_max      77.2330

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    1.045
_shelx_estimated_absorpt_T_min   0.573
_shelx_estimated_absorpt_T_max   0.759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72184
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8496
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.051
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_full        67.076
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2627
_reflns_number_gt                2184
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2500P)²+0.5592P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2627
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.1005
_refine_ls_wR_factor_ref         0.3419
_refine_ls_wR_factor_gt          0.3130
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.42882(17) 0.8264(2) 0.2007(3) 0.0564(7) Uani 1 1 d . . . . .
O2 O 0.4402(2) 0.6240(2) 0.1569(4) 0.0778(9) Uani 1 1 d . . . . .
O3 O 0.25975(18) 0.7936(2) 0.0616(2) 0.0609(7) Uani 1 1 d . . . . .
N1 N 0.20891(19) 0.6867(3) 0.2498(3) 0.0515(7) Uani 1 1 d . . . . .
F1 F 0.8608(5) 0.8397(10) -0.0846(7) 0.0810(17) Uiso 0.4 1 d . . P A 1
F2 F 0.7891(7) 0.9537(8) -0.2270(12) 0.0721(19) Uiso 0.3 1 d . . P A 1
F3 F 0.7979(5) 0.7585(7) -0.2756(8) 0.0680(14) Uiso 0.4 1 d . . P A 1
F1A F 0.8459(7) 0.9099(11) -0.0915(10) 0.078(2) Uiso 0.3 1 d . . P A 2
F2A F 0.7618(7) 0.9249(9) -0.2792(10) 0.100(2) Uiso 0.4 1 d . . P A 2
F3A F 0.8248(10) 0.7444(12) -0.2159(17) 0.107(3) Uiso 0.3 1 d . . P A 2
F1B F 0.8615(8) 0.7748(12) -0.1027(12) 0.091(3) Uiso 0.3 1 d . . P A 3
F2B F 0.8185(8) 0.9584(10) -0.1549(15) 0.093(3) Uiso 0.3 1 d . . P A 3
F3B F 0.7838(8) 0.8163(13) -0.2999(13) 0.098(3) Uiso 0.3 1 d . . P A 3
C1 C 0.4682(2) 0.7282(3) 0.1426(3) 0.0528(8) Uani 1 1 d . . . . .
C2 C 0.5479(2) 0.7622(3) 0.0597(3) 0.0493(8) Uani 1 1 d . . . . .
C3 C 0.5884(3) 0.6704(3) -0.0186(4) 0.0577(9) Uani 1 1 d . . . . .
H3 H 0.5643 0.5906 -0.0194 0.069 Uiso 1 1 calc R U . . .
C4 C 0.6644(3) 0.6969(3) -0.0954(4) 0.0609(9) Uani 1 1 d . . . . .
H4 H 0.6911 0.6353 -0.1483 0.073 Uiso 1 1 calc R U . . .
C5 C 0.7004(2) 0.8154(3) -0.0930(4) 0.0564(9) Uani 1 1 d . . . . .
C6 C 0.6591(2) 0.9085(3) -0.0176(4) 0.0582(9) Uani 1 1 d . . . . .
H6 H 0.6826 0.9885 -0.0183 0.070 Uiso 1 1 calc R U . . .
C7 C 0.5831(2) 0.8820(3) 0.0585(3) 0.0528(8) Uani 1 1 d . . . . .
H7 H 0.5554 0.9443 0.1090 0.063 Uiso 1 1 calc R U . . .
C8 C 0.7850(3) 0.8415(5) -0.1711(5) 0.0737(11) Uani 1 1 d . . . . .
C9 C 0.3515(3) 0.7986(4) 0.2818(4) 0.0617(9) Uani 1 1 d . . . . .
H9A H 0.3353 0.8712 0.3355 0.074 Uiso 1 1 calc R U . . .
H9B H 0.3680 0.7330 0.3490 0.074 Uiso 1 1 calc R U . . .
C10 C 0.2679(2) 0.7580(3) 0.1853(3) 0.0488(8) Uani 1 1 d . . . . .
C11 C 0.1206(3) 0.6374(4) 0.1852(4) 0.0658(8) Uani 1 1 d . . . . .
C12 C 0.1365(3) 0.5711(4) 0.0466(4) 0.0658(8) Uani 1 1 d . . . . .
H12A H 0.1638 0.6272 -0.0177 0.099 Uiso 1 1 calc R U . . .
H12B H 0.0785 0.5419 0.0046 0.099 Uiso 1 1 calc R U . . .
H12C H 0.1771 0.5021 0.0654 0.099 Uiso 1 1 calc R U . . .
C13 C 0.0526(3) 0.7420(5) 0.1604(6) 0.0837(13) Uani 1 1 d . . . . .
H13A H 0.0429 0.7821 0.2492 0.126 Uiso 1 1 calc R U . . .
H13B H -0.0049 0.7098 0.1204 0.126 Uiso 1 1 calc R U . . .
H13C H 0.0767 0.8006 0.0956 0.126 Uiso 1 1 calc R U . . .
C14 C 0.0845(4) 0.5468(5) 0.2919(5) 0.0875(14) Uani 1 1 d . . . . .
H14A H 0.1272 0.4793 0.3056 0.131 Uiso 1 1 calc R U . . .
H14B H 0.0255 0.5156 0.2566 0.131 Uiso 1 1 calc R U . . .
H14C H 0.0781 0.5881 0.3810 0.131 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
O1 C1 1.338(4) . ?
O1 C9 1.428(4) . ?
O2 C1 1.208(4) . ?
O3 C10 1.225(4) . ?
N1 C10 1.326(4) . ?
N1 C11 1.484(4) . ?
F1 C8 1.328(8) . ?
F2 C8 1.325(9) . ?
F3 C8 1.353(8) . ?
F1A C8 1.344(10) . ?
F2A C8 1.384(10) . ?
F3A C8 1.282(14) . ?
F1B C8 1.442(12) . ?
F2B C8 1.359(11) . ?
F3B C8 1.242(13) . ?
C1 C2 1.481(5) . ?
C2 C3 1.388(5) . ?
C2 C7 1.393(4) . ?
C3 C4 1.386(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(5) . ?
C5 C8 1.496(6) . ?
C6 C7 1.381(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C9 C10 1.534(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C13 1.508(6) . ?
C11 C12 1.518(5) . ?
C11 C14 1.519(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C9 114.8(3) . . ?
C10 N1 C11 125.9(3) . . ?
O2 C1 O1 122.7(3) . . ?
O2 C1 C2 124.7(3) . . ?
O1 C1 C2 112.6(3) . . ?
C3 C2 C7 119.6(3) . . ?
C3 C2 C1 118.2(3) . . ?
C7 C2 C1 122.3(3) . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 C8 119.2(3) . . ?
C6 C5 C8 120.4(3) . . ?
C7 C6 C5 119.9(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C2 120.1(3) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
F2 C8 F1 101.6(7) . . ?
F3A C8 F1A 109.8(9) . . ?
F2 C8 F3 107.9(6) . . ?
F1 C8 F3 106.8(6) . . ?
F3B C8 F2B 107.3(9) . . ?
F3A C8 F2A 112.7(9) . . ?
F1A C8 F2A 99.9(7) . . ?
F3B C8 F1B 106.8(9) . . ?
F2B C8 F1B 98.9(8) . . ?
F3B C8 C5 118.4(7) . . ?
F3A C8 C5 114.0(7) . . ?
F2 C8 C5 115.2(5) . . ?
F1 C8 C5 111.7(4) . . ?
F1A C8 C5 111.2(5) . . ?
F3 C8 C5 112.7(4) . . ?
F2B C8 C5 114.8(6) . . ?
F2A C8 C5 108.3(5) . . ?
F1B C8 C5 108.6(5) . . ?
O1 C9 C10 111.3(3) . . ?
O1 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
O1 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
O3 C10 N1 126.2(3) . . ?
O3 C10 C9 119.9(3) . . ?
N1 C10 C9 113.9(3) . . ?
N1 C11 C13 109.5(3) . . ?
N1 C11 C12 110.4(3) . . ?
C13 C11 C12 110.7(4) . . ?
N1 C11 C14 106.6(3) . . ?
C13 C11 C14 109.7(4) . . ?
C12 C11 C14 109.8(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         0.686
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.082



