# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

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

data_1
_audit_block_doi                 10.5517/ccdc.csd.cc2jmmh9
_database_code_depnum_ccdc_archive 'CCDC 2342561'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/d4ob00494a 2024
loop_
_audit_author_name
_audit_author_address
'xiao geng'
;Taizhou University
China
;
_audit_update_record             
;
2024-03-22 deposited with the CCDC.	2024-05-08 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         ?
_chemical_formula_sum            'C16 H9 N3 O'
_chemical_formula_weight         259.26

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.5878(4)
_cell_length_b                   9.5702(3)
_cell_length_c                   21.3754(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2575.05(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9963
_cell_measurement_theta_min      5.43
_cell_measurement_theta_max      68.22

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.704
_shelx_estimated_absorpt_T_min   0.849
_shelx_estimated_absorpt_T_max   0.872
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23263
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         5.429
_diffrn_reflns_theta_max         68.293
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2340
_reflns_number_gt                2080
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0545P)²+0.2497P] 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         2340
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 0.69887(8) 0.63610(9) 0.65639(5) 0.0684(3) Uani 1 1 d . . . . .
N0AA N 0.63260(7) 0.35554(9) 0.56120(4) 0.0510(2) Uani 1 1 d . . . . .
N2 N 0.85655(8) 0.34494(11) 0.55215(5) 0.0602(3) Uani 1 1 d . . . . .
C15 C 0.68178(9) 0.27054(11) 0.51883(5) 0.0480(3) Uani 1 1 d . . . . .
C8 C 0.69491(9) 0.43146(11) 0.59666(5) 0.0489(3) Uani 1 1 d . . . . .
C7 C 0.64623(10) 0.53390(11) 0.64187(5) 0.0522(3) Uani 1 1 d . . . . .
C10 C 0.79395(9) 0.26380(12) 0.51484(5) 0.0512(3) Uani 1 1 d . . . . .
C6 C 0.53836(10) 0.51057(12) 0.66753(5) 0.0542(3) Uani 1 1 d . . . . .
C14 C 0.61986(10) 0.18823(12) 0.47842(6) 0.0572(3) Uani 1 1 d . . . . .
H14 H 0.5461 0.1930 0.4802 0.069 Uiso 1 1 calc R U . . .
C9 C 0.80743(10) 0.42677(12) 0.59152(6) 0.0560(3) Uani 1 1 d . . . . .
H9 H 0.8477 0.4844 0.6173 0.067 Uiso 1 1 calc R U . . .
C13 C 0.66836(10) 0.10103(12) 0.43651(6) 0.0554(3) Uani 1 1 d . . . . .
C5 C 0.50020(11) 0.37799(14) 0.68105(5) 0.0609(3) Uani 1 1 d . . . . .
H5 H 0.5398 0.2996 0.6701 0.073 Uiso 1 1 calc R U . . .
C12 C 0.78003(10) 0.09054(14) 0.43376(6) 0.0610(3) Uani 1 1 d . . . . .
H12 H 0.8118 0.0287 0.4059 0.073 Uiso 1 1 calc R U . . .
C11 C 0.84104(10) 0.17081(13) 0.47181(6) 0.0629(3) Uani 1 1 d . . . . .
H11 H 0.9147 0.1644 0.4695 0.076 Uiso 1 1 calc R U . . .
C16 C 0.60447(12) 0.01931(14) 0.39415(7) 0.0708(4) Uani 1 1 d . . . . .
N1 N 0.55424(13) -0.04395(17) 0.36001(8) 0.1039(5) Uani 1 1 d . . . . .
C1 C 0.47674(13) 0.62693(15) 0.68274(7) 0.0731(4) Uani 1 1 d . . . . .
H1 H 0.5011 0.7164 0.6737 0.088 Uiso 1 1 calc R U . . .
C4 C 0.40360(12) 0.36223(18) 0.71072(6) 0.0760(4) Uani 1 1 d . . . . .
H4 H 0.3792 0.2733 0.7208 0.091 Uiso 1 1 calc R U . . .
C2 C 0.37938(14) 0.6084(2) 0.71125(9) 0.0915(5) Uani 1 1 d . U . . .
H2 H 0.3377 0.6856 0.7209 0.110 Uiso 1 1 calc R U . . .
C3 C 0.34364(14) 0.4765(2) 0.72541(7) 0.0905(5) Uani 1 1 d . U . . .
H3 H 0.2783 0.4650 0.7451 0.109 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 C7 1.2216(14) . ?
N0AA C8 1.3105(14) . ?
N0AA C15 1.3659(14) . ?
N2 C9 1.3054(16) . ?
N2 C10 1.3639(15) . ?
C15 C14 1.4050(16) . ?
C15 C10 1.4161(16) . ?
C8 C9 1.4213(17) . ?
C8 C7 1.5069(15) . ?
C7 C6 1.4814(18) . ?
C10 C11 1.4103(16) . ?
C6 C5 1.3872(17) . ?
C6 C1 1.3955(17) . ?
C14 C13 1.3681(16) . ?
C14 H14 0.9300 . ?
C9 H9 0.9300 . ?
C13 C12 1.4105(19) . ?
C13 C16 1.4416(18) . ?
C5 C4 1.380(2) . ?
C5 H5 0.9300 . ?
C12 C11 1.3570(18) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C16 N1 1.1396(19) . ?
C1 C2 1.380(2) . ?
C1 H1 0.9300 . ?
C4 C3 1.366(2) . ?
C4 H4 0.9300 . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N0AA C15 116.26(10) . . ?
C9 N2 C10 116.42(10) . . ?
N0AA C15 C14 119.35(10) . . ?
N0AA C15 C10 121.27(10) . . ?
C14 C15 C10 119.38(10) . . ?
N0AA C8 C9 122.30(10) . . ?
N0AA C8 C7 119.22(10) . . ?
C9 C8 C7 118.38(10) . . ?
O1 C7 C6 121.59(11) . . ?
O1 C7 C8 117.60(11) . . ?
C6 C7 C8 120.81(10) . . ?
N2 C10 C11 119.86(11) . . ?
N2 C10 C15 120.99(10) . . ?
C11 C10 C15 119.15(10) . . ?
C5 C6 C1 119.27(13) . . ?
C5 C6 C7 122.17(11) . . ?
C1 C6 C7 118.39(12) . . ?
C13 C14 C15 119.80(11) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
N2 C9 C8 122.74(11) . . ?
N2 C9 H9 118.6 . . ?
C8 C9 H9 118.6 . . ?
C14 C13 C12 121.02(11) . . ?
C14 C13 C16 119.55(12) . . ?
C12 C13 C16 119.42(11) . . ?
C4 C5 C6 120.06(13) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C11 C12 C13 119.92(11) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C11 C10 120.68(11) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
N1 C16 C13 179.03(19) . . ?
C2 C1 C6 119.59(15) . . ?
C2 C1 H1 120.2 . . ?
C6 C1 H1 120.2 . . ?
C3 C4 C5 120.35(16) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C3 C2 C1 120.42(15) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 120.28(16) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?

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
C8 N0AA C15 C14 -178.75(10) . . . . ?
C8 N0AA C15 C10 1.24(15) . . . . ?
C15 N0AA C8 C9 0.23(15) . . . . ?
C15 N0AA C8 C7 176.46(9) . . . . ?
N0AA C8 C7 O1 -153.04(11) . . . . ?
C9 C8 C7 O1 23.34(15) . . . . ?
N0AA C8 C7 C6 26.96(15) . . . . ?
C9 C8 C7 C6 -156.66(10) . . . . ?
C9 N2 C10 C11 -178.91(11) . . . . ?
C9 N2 C10 C15 0.65(17) . . . . ?
N0AA C15 C10 N2 -1.76(16) . . . . ?
C14 C15 C10 N2 178.23(11) . . . . ?
N0AA C15 C10 C11 177.81(10) . . . . ?
C14 C15 C10 C11 -2.21(16) . . . . ?
O1 C7 C6 C5 -144.69(12) . . . . ?
C8 C7 C6 C5 35.31(16) . . . . ?
O1 C7 C6 C1 30.49(17) . . . . ?
C8 C7 C6 C1 -149.51(11) . . . . ?
N0AA C15 C14 C13 -178.93(11) . . . . ?
C10 C15 C14 C13 1.09(17) . . . . ?
C10 N2 C9 C8 0.82(17) . . . . ?
N0AA C8 C9 N2 -1.34(18) . . . . ?
C7 C8 C9 N2 -177.60(11) . . . . ?
C15 C14 C13 C12 1.00(19) . . . . ?
C15 C14 C13 C16 -178.53(12) . . . . ?
C1 C6 C5 C4 -1.70(19) . . . . ?
C7 C6 C5 C4 173.44(11) . . . . ?
C14 C13 C12 C11 -1.97(19) . . . . ?
C16 C13 C12 C11 177.56(13) . . . . ?
C13 C12 C11 C10 0.8(2) . . . . ?
N2 C10 C11 C12 -179.17(12) . . . . ?
C15 C10 C11 C12 1.26(18) . . . . ?
C5 C6 C1 C2 0.4(2) . . . . ?
C7 C6 C1 C2 -174.95(13) . . . . ?
C6 C5 C4 C3 1.8(2) . . . . ?
C6 C1 C2 C3 0.9(2) . . . . ?
C5 C4 C3 C2 -0.5(2) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H14 N2 0.93 2.51 3.3932(16) 158.5 4_456

_refine_diff_density_max         0.133
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.029

####################################################################### 
# 
# 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_1_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc2jmmjb
_database_code_depnum_ccdc_archive 'CCDC 2342562'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/d4ob00494a 2024
loop_
_audit_author_name
_audit_author_address
'xiao geng'
;Taizhou University
China
;
_audit_update_record             
;
2024-03-22 deposited with the CCDC.	2024-05-08 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         ?
_chemical_formula_sum            'C18 H13 F3 N2 O'
_chemical_formula_weight         330.30

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.2674(4)
_cell_length_b                   9.6649(6)
_cell_length_c                   11.5209(7)
_cell_angle_alpha                93.372(3)
_cell_angle_beta                 95.007(3)
_cell_angle_gamma                97.994(3)
_cell_volume                     796.22(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    5357
_cell_measurement_theta_min      3.86
_cell_measurement_theta_max      68.28

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.947
_shelx_estimated_absorpt_T_min   0.791
_shelx_estimated_absorpt_T_max   0.819
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      301(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11329
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.632
_diffrn_reflns_theta_max         68.383
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2920
_reflns_number_gt                2254
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0942P)²+0.0623P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2920
_refine_ls_number_parameters     257
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1664
_refine_ls_wR_factor_gt          0.1538
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_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
N1 N 0.50332(17) 0.58636(14) 0.82764(11) 0.0615(4) Uani 1 1 d . . . . .
N2 N 0.81395(19) 0.61936(15) 0.99758(13) 0.0706(4) Uani 1 1 d . . . . .
O1 O 0.7975(2) 0.3774(2) 0.69860(14) 0.1181(7) Uani 1 1 d . . . . .
C18 C 0.5108(2) 0.67351(15) 0.92579(13) 0.0572(4) Uani 1 1 d . . . . .
C11 C 0.6674(2) 0.69109(15) 1.01035(14) 0.0592(4) Uani 1 1 d . . . . .
C9 C 0.6458(2) 0.51789(16) 0.81725(14) 0.0611(4) Uani 1 1 d . . . . .
C10 C 0.8009(2) 0.53437(18) 0.90330(16) 0.0692(5) Uani 1 1 d . . . . .
H10 H 0.8976 0.4826 0.8923 0.083 Uiso 1 1 calc R U . . .
C12 C 0.6683(2) 0.78330(17) 1.10954(15) 0.0681(4) Uani 1 1 d . . . . .
H12 H 0.7720 0.7971 1.1644 0.082 Uiso 1 1 calc R U . . .
C15 C 0.3614(2) 0.83369(16) 1.04287(15) 0.0662(4) Uani 1 1 d . . . . .
C5 C 0.4867(2) 0.37407(17) 0.62295(14) 0.0659(4) Uani 1 1 d . . . . .
C13 C 0.5208(2) 0.85325(16) 1.12751(15) 0.0671(4) Uani 1 1 d . . . . .
C17 C 0.3597(2) 0.74626(16) 0.94510(15) 0.0658(4) Uani 1 1 d . . . . .
H17 H 0.2564 0.7344 0.8899 0.079 Uiso 1 1 calc R U . . .
C6 C 0.3035(2) 0.3887(2) 0.63852(16) 0.0756(5) Uani 1 1 d . . . . .
H6 H 0.2763 0.4368 0.7058 0.091 Uiso 1 1 calc R U . . .
F2 F 0.0881(12) 0.2093(9) 0.2604(4) 0.153(4) Uani 0.477(10) 1 d D . P A 1
C8 C 0.6514(2) 0.4211(2) 0.71122(16) 0.0726(5) Uani 1 1 d . . . . .
C2 C 0.2002(3) 0.2625(2) 0.45458(16) 0.0800(5) Uani 1 1 d D . . . .
C4 C 0.5236(3) 0.3050(2) 0.52078(16) 0.0805(5) Uani 1 1 d . . . . .
H4 H 0.6462 0.2956 0.5086 0.097 Uiso 1 1 calc R U . . .
C7 C 0.1609(3) 0.3325(2) 0.55501(17) 0.0836(6) Uani 1 1 d . . . . .
H7 H 0.0380 0.3418 0.5665 0.100 Uiso 1 1 calc R U . . .
C16 C 0.1957(3) 0.9063(2) 1.0625(2) 0.0903(6) Uani 1 1 d . . . . .
H16A H 0.1404 0.8729 1.1301 0.136 Uiso 1 1 calc R U . . .
H16B H 0.1056 0.8868 0.9954 0.136 Uiso 1 1 calc R U . . .
H16C H 0.2352 1.0055 1.0744 0.136 Uiso 1 1 calc R U . . .
C14 C 0.5258(3) 0.9494(2) 1.23576(18) 0.0889(6) Uani 1 1 d . . . . .
H14A H 0.6363 0.9436 1.2863 0.133 Uiso 1 1 calc R U . . .
H14B H 0.4175 0.9221 1.2758 0.133 Uiso 1 1 calc R U . . .
H14C H 0.5268 1.0440 1.2143 0.133 Uiso 1 1 calc R U . . .
C3 C 0.3817(3) 0.2501(2) 0.43700(17) 0.0881(6) Uani 1 1 d . . . . .
H3 H 0.4086 0.2045 0.3685 0.106 Uiso 1 1 calc R U . . .
F3 F -0.1145(7) 0.2127(18) 0.3818(10) 0.214(7) Uani 0.477(10) 1 d D . P A 1
C1 C 0.0471(10) 0.1880(12) 0.3660(7) 0.092(4) Uani 0.477(10) 1 d D . P A 1
F1 F 0.0362(13) 0.0466(6) 0.3626(7) 0.154(3) Uani 0.477(10) 1 d D . P A 1
F2A F 0.0873(10) 0.1518(14) 0.2723(7) 0.201(5) Uani 0.523(10) 1 d D . P A 2
F3A F -0.0559(13) 0.3064(8) 0.3307(7) 0.179(4) Uani 0.523(10) 1 d D . P A 2
C1A C 0.0405(14) 0.2163(14) 0.3620(9) 0.123(5) Uani 0.523(10) 1 d D . P A 2
F1A F -0.0747(13) 0.1186(10) 0.4081(7) 0.170(4) Uani 0.523(10) 1 d D . P A 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9 1.3145(19) . ?
N1 C18 1.3622(19) . ?
N2 C10 1.311(2) . ?
N2 C11 1.3629(19) . ?
O1 C8 1.2128(19) . ?
C18 C17 1.410(2) . ?
C18 C11 1.416(2) . ?
C11 C12 1.406(2) . ?
C9 C10 1.420(2) . ?
C9 C8 1.501(2) . ?
C10 H10 0.9300 . ?
C12 C13 1.368(2) . ?
C12 H12 0.9300 . ?
C15 C17 1.366(2) . ?
C15 C13 1.431(3) . ?
C15 C16 1.503(2) . ?
C5 C4 1.384(2) . ?
C5 C6 1.385(2) . ?
C5 C8 1.502(2) . ?
C13 C14 1.506(2) . ?
C17 H17 0.9300 . ?
C6 C7 1.380(3) . ?
C6 H6 0.9300 . ?
F2 C1 1.299(10) . ?
C2 C3 1.372(3) . ?
C2 C7 1.377(2) . ?
C2 C1A 1.506(10) . ?
C2 C1 1.513(6) . ?
C4 C3 1.375(3) . ?
C4 H4 0.9300 . ?
C7 H7 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C3 H3 0.9300 . ?
F3 C1 1.257(10) . ?
C1 F1 1.356(12) . ?
F2A C1A 1.272(9) . ?
F3A C1A 1.242(12) . ?
C1A F1A 1.338(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C18 116.70(13) . . ?
C10 N2 C11 116.22(14) . . ?
N1 C18 C17 119.89(14) . . ?
N1 C18 C11 121.06(13) . . ?
C17 C18 C11 119.05(14) . . ?
N2 C11 C12 120.13(14) . . ?
N2 C11 C18 121.23(14) . . ?
C12 C11 C18 118.64(14) . . ?
N1 C9 C10 121.90(14) . . ?
N1 C9 C8 120.52(14) . . ?
C10 C9 C8 117.57(13) . . ?
N2 C10 C9 122.87(14) . . ?
N2 C10 H10 118.6 . . ?
C9 C10 H10 118.6 . . ?
C13 C12 C11 121.82(15) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C17 C15 C13 119.40(14) . . ?
C17 C15 C16 120.23(16) . . ?
C13 C15 C16 120.36(15) . . ?
C4 C5 C6 118.56(16) . . ?
C4 C5 C8 116.12(15) . . ?
C6 C5 C8 125.25(14) . . ?
C12 C13 C15 119.47(14) . . ?
C12 C13 C14 120.25(17) . . ?
C15 C13 C14 120.28(16) . . ?
C15 C17 C18 121.61(15) . . ?
C15 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C7 C6 C5 120.46(15) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O1 C8 C9 117.15(16) . . ?
O1 C8 C5 119.05(15) . . ?
C9 C8 C5 123.79(13) . . ?
C3 C2 C7 119.96(17) . . ?
C3 C2 C1A 122.5(4) . . ?
C7 C2 C1A 117.2(4) . . ?
C3 C2 C1 118.1(4) . . ?
C7 C2 C1 121.7(4) . . ?
C3 C4 C5 120.98(17) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C2 C7 C6 120.09(17) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C3 C4 119.92(16) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
F3 C1 F2 112.0(9) . . ?
F3 C1 F1 105.3(9) . . ?
F2 C1 F1 99.9(7) . . ?
F3 C1 C2 115.0(7) . . ?
F2 C1 C2 110.6(7) . . ?
F1 C1 C2 112.9(6) . . ?
F3A C1A F2A 109.3(11) . . ?
F3A C1A F1A 106.1(9) . . ?
F2A C1A F1A 103.6(11) . . ?
F3A C1A C2 117.0(9) . . ?
F2A C1A C2 113.6(8) . . ?
F1A C1A C2 105.9(8) . . ?

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
C9 N1 C18 C17 -177.56(14) . . . . ?
C9 N1 C18 C11 1.5(2) . . . . ?
C10 N2 C11 C12 179.22(15) . . . . ?
C10 N2 C11 C18 0.1(2) . . . . ?
N1 C18 C11 N2 -1.4(2) . . . . ?
C17 C18 C11 N2 177.72(14) . . . . ?
N1 C18 C11 C12 179.47(13) . . . . ?
C17 C18 C11 C12 -1.5(2) . . . . ?
C18 N1 C9 C10 -0.5(2) . . . . ?
C18 N1 C9 C8 -179.08(14) . . . . ?
C11 N2 C10 C9 1.0(3) . . . . ?
N1 C9 C10 N2 -0.8(3) . . . . ?
C8 C9 C10 N2 177.81(15) . . . . ?
N2 C11 C12 C13 -177.59(15) . . . . ?
C18 C11 C12 C13 1.6(2) . . . . ?
C11 C12 C13 C15 -0.6(3) . . . . ?
C11 C12 C13 C14 179.05(16) . . . . ?
C17 C15 C13 C12 -0.5(2) . . . . ?
C16 C15 C13 C12 178.28(16) . . . . ?
C17 C15 C13 C14 179.84(15) . . . . ?
C16 C15 C13 C14 -1.4(3) . . . . ?
C13 C15 C17 C18 0.6(2) . . . . ?
C16 C15 C17 C18 -178.17(16) . . . . ?
N1 C18 C17 C15 179.47(14) . . . . ?
C11 C18 C17 C15 0.4(2) . . . . ?
C4 C5 C6 C7 1.6(3) . . . . ?
C8 C5 C6 C7 -175.18(19) . . . . ?
N1 C9 C8 O1 169.35(18) . . . . ?
C10 C9 C8 O1 -9.3(3) . . . . ?
N1 C9 C8 C5 -12.0(3) . . . . ?
C10 C9 C8 C5 169.37(16) . . . . ?
C4 C5 C8 O1 -12.1(3) . . . . ?
C6 C5 C8 O1 164.7(2) . . . . ?
C4 C5 C8 C9 169.23(17) . . . . ?
C6 C5 C8 C9 -13.9(3) . . . . ?
C6 C5 C4 C3 -1.0(3) . . . . ?
C8 C5 C4 C3 176.09(18) . . . . ?
C3 C2 C7 C6 -0.7(3) . . . . ?
C1A C2 C7 C6 -174.1(6) . . . . ?
C1 C2 C7 C6 174.3(5) . . . . ?
C5 C6 C7 C2 -0.8(3) . . . . ?
C7 C2 C3 C4 1.3(3) . . . . ?
C1A C2 C3 C4 174.4(7) . . . . ?
C1 C2 C3 C4 -173.9(5) . . . . ?
C5 C4 C3 C2 -0.5(3) . . . . ?
C3 C2 C1 F3 -174.4(11) . . . . ?
C7 C2 C1 F3 10.4(14) . . . . ?
C3 C2 C1 F2 -46.3(11) . . . . ?
C7 C2 C1 F2 138.6(8) . . . . ?
C3 C2 C1 F1 64.7(10) . . . . ?
C7 C2 C1 F1 -110.4(7) . . . . ?
C3 C2 C1A F3A -121.8(9) . . . . ?
C7 C2 C1A F3A 51.5(12) . . . . ?
C3 C2 C1A F2A 7.2(15) . . . . ?
C7 C2 C1A F2A -179.6(10) . . . . ?
C3 C2 C1A F1A 120.3(8) . . . . ?
C7 C2 C1A F1A -66.5(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10 N2 0.93 2.69 3.485(2) 143.9 2_767

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.042

