# Supplementary Information (SI) for RSC Advances.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2324482'
loop_
_audit_author_name
_audit_author_address
'Zhongjie Wang'
; College of Chemistry and Chemical Engineering Ningxia University Yinchuan 
China
;
_audit_update_record             
;
2024-01-10 deposited with the CCDC.	2024-07-16 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            'C15 H12 Br2 N2'
_chemical_formula_weight         380.09

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   11.438(12)
_cell_length_b                   25.58(3)
_cell_length_c                   4.893(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1432(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2917
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      24.15

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    5.649
_shelx_estimated_absorpt_T_min   0.550
_shelx_estimated_absorpt_T_max   0.661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10532
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.185
_diffrn_reflns_theta_max         24.883
_diffrn_reflns_theta_full        24.883
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             1261
_reflns_number_gt                893
_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)+(0.0241P)²+0.5337P] 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         1261
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0626
_refine_ls_wR_factor_gt          0.0569
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
Br1 Br 0.66347(3) 0.46498(2) 0.94414(8) 0.05657(18) Uani 1 1 d . . . . .
C1 C 0.3691(4) 0.2500 0.4358(10) 0.0409(11) Uani 1 2 d S T P . .
C2 C 0.4843(3) 0.30026(12) 0.1181(6) 0.0494(9) Uani 1 1 d . . . . .
H2A H 0.4158 0.3132 0.0230 0.059 Uiso 1 1 calc R U . . .
H2B H 0.5455 0.2946 -0.0160 0.059 Uiso 1 1 calc R U . . .
C3 C 0.5244(3) 0.34039(12) 0.3230(6) 0.0418(8) Uani 1 1 d . . . . .
C4 C 0.4587(3) 0.38436(13) 0.3843(7) 0.0481(9) Uani 1 1 d . . . . .
H4 H 0.3869 0.3891 0.2985 0.058 Uiso 1 1 calc R U . . .
C5 C 0.4968(3) 0.42129(13) 0.5688(7) 0.0519(9) Uani 1 1 d . . . . .
H5 H 0.4513 0.4504 0.6084 0.062 Uiso 1 1 calc R U . . .
C6 C 0.6046(3) 0.41423(12) 0.6945(6) 0.0401(8) Uani 1 1 d . . . . .
C7 C 0.6717(3) 0.37035(13) 0.6403(7) 0.0494(9) Uani 1 1 d . . . . .
H7 H 0.7432 0.3655 0.7269 0.059 Uiso 1 1 calc R U . . .
C8 C 0.6303(3) 0.33402(14) 0.4552(7) 0.0493(9) Uani 1 1 d . . . . .
H8 H 0.6749 0.3044 0.4184 0.059 Uiso 1 1 calc R U . . .
N1 N 0.4556(3) 0.2500 0.2535(7) 0.0435(9) Uani 1 2 d S T P . .
N2 N 0.2966(4) 0.2500 0.5969(9) 0.0626(12) Uani 1 2 d S T P . .


_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
Br1 C6 1.905(3) . ?
C1 N2 1.144(6) . ?
C1 N1 1.332(6) . ?
C2 N1 1.483(4) . ?
C2 C3 1.506(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C8 1.383(4) . ?
C3 C4 1.385(4) . ?
C4 C5 1.378(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(4) . ?
C7 C8 1.382(5) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
N1 C2 1.483(4) 7_565 ?

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
N2 C1 N1 178.5(5) . . ?
N1 C2 C3 111.1(3) . . ?
N1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C8 C3 C4 118.0(3) . . ?
C8 C3 C2 119.8(3) . . ?
C4 C3 C2 122.2(3) . . ?
C5 C4 C3 121.8(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 118.8(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 Br1 118.6(2) . . ?
C5 C6 Br1 120.6(2) . . ?
C8 C7 C6 118.7(3) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C7 C8 C3 121.9(3) . . ?
C7 C8 H8 119.1 . . ?
C3 C8 H8 119.1 . . ?
C1 N1 C2 117.6(2) . . ?
C1 N1 C2 117.6(2) . 7_565 ?
C2 N1 C2 120.2(4) . 7_565 ?

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
N1 C2 C3 C8 68.5(4) . . . . ?
N1 C2 C3 C4 -112.0(3) . . . . ?
C8 C3 C4 C5 0.6(5) . . . . ?
C2 C3 C4 C5 -179.0(3) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C4 C5 C6 C7 -1.3(5) . . . . ?
C4 C5 C6 Br1 178.4(2) . . . . ?
C5 C6 C7 C8 1.0(5) . . . . ?
Br1 C6 C7 C8 -178.7(2) . . . . ?
C6 C7 C8 C3 0.2(5) . . . . ?
C4 C3 C8 C7 -1.0(5) . . . . ?
C2 C3 C8 C7 178.6(3) . . . . ?
C3 C2 N1 C1 62.1(4) . . . . ?
C3 C2 N1 C2 -142.5(3) . . . 7_565 ?

_refine_diff_density_max         0.414
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2324486'
loop_
_audit_author_name
_audit_author_address
'Zhongjie Wang'
; College of Chemistry and Chemical Engineering Ningxia University Yinchuan 
China
;
_audit_update_record             
;
2024-01-10 deposited with the CCDC.	2024-07-16 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            'C15 H12 N4 O4'
_chemical_formula_weight         312.29

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.0138(8)
_cell_length_b                   13.9046(14)
_cell_length_c                   11.9428(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.927(2)
_cell_angle_gamma                90
_cell_volume                     1469.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1758
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      24.04

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12587
_diffrn_reflns_av_unetI/netI     0.0822
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.728
_diffrn_reflns_theta_max         25.118
_diffrn_reflns_theta_full        25.118
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2587
_reflns_number_gt                1227
_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)+(0.0705P)²+0.3746P] 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         2587
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1639
_refine_ls_R_factor_gt           0.0638
_refine_ls_wR_factor_ref         0.1693
_refine_ls_wR_factor_gt          0.1276
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_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
C1 C 0.7398(4) 0.6991(2) 0.2356(3) 0.0530(9) Uani 1 1 d . . . . .
C3 C 0.5890(4) 0.5655(2) 0.1626(3) 0.0529(9) Uani 1 1 d . . . . .
H3 H 0.5642 0.5171 0.1085 0.064 Uiso 1 1 calc R U . . .
C4 C 0.5108(3) 0.5733(2) 0.2512(3) 0.0432(8) Uani 1 1 d . . . . .
C5 C 0.5492(4) 0.6464(2) 0.3307(3) 0.0515(9) Uani 1 1 d . . . . .
H5 H 0.4963 0.6525 0.3901 0.062 Uiso 1 1 calc R U . . .
C6 C 0.6640(4) 0.7099(2) 0.3234(3) 0.0530(9) Uani 1 1 d . . . . .
H6 H 0.6892 0.7587 0.3768 0.064 Uiso 1 1 calc R U . . .
C7 C 0.3925(3) 0.5020(2) 0.2685(3) 0.0532(9) Uani 1 1 d . . . . .
H7A H 0.4418 0.4459 0.3069 0.064 Uiso 1 1 calc R U . . .
H7B H 0.3304 0.5303 0.3179 0.064 Uiso 1 1 calc R U . . .
C8 C 0.2260(4) 0.5396(3) 0.0927(3) 0.0577(10) Uani 1 1 d . . . . .
C9 C 0.2097(4) 0.3815(2) 0.1694(3) 0.0558(9) Uani 1 1 d . . . . .
H9A H 0.2807 0.3286 0.1847 0.067 Uiso 1 1 calc R U . . .
H9B H 0.1443 0.3694 0.0964 0.067 Uiso 1 1 calc R U . . .
C10 C 0.1151(3) 0.3840(2) 0.2609(3) 0.0451(8) Uani 1 1 d . . . . .
C11 C -0.0021(4) 0.4499(2) 0.2554(3) 0.0515(9) Uani 1 1 d . . . . .
H11 H -0.0208 0.4935 0.1954 0.062 Uiso 1 1 calc R U . . .
C12 C -0.0905(4) 0.4517(2) 0.3369(3) 0.0525(9) Uani 1 1 d . . . . .
H12 H -0.1685 0.4961 0.3328 0.063 Uiso 1 1 calc R U . . .
C13 C -0.0614(4) 0.3863(3) 0.4253(3) 0.0516(9) Uani 1 1 d . . . . .
C14 C 0.0536(4) 0.3207(3) 0.4339(3) 0.0568(10) Uani 1 1 d . . . . .
H14 H 0.0714 0.2771 0.4939 0.068 Uiso 1 1 calc R U . . .
C15 C 0.1424(4) 0.3207(2) 0.3518(3) 0.0548(9) Uani 1 1 d . . . . .
H15 H 0.2221 0.2773 0.3577 0.066 Uiso 1 1 calc R U . . .
C2N C 0.7040(4) 0.6293(3) 0.1538(3) 0.0575(10) Uani 1 1 d . . . . .
H2N H 0.7560 0.6250 0.0937 0.069 Uiso 1 1 calc R U . . .
N1 N 0.2943(3) 0.47138(19) 0.1618(2) 0.0490(7) Uani 1 1 d . . . . .
N2 N 0.1717(4) 0.5977(3) 0.0301(3) 0.0934(13) Uani 1 1 d . . . . .
N3 N 0.8651(4) 0.7656(3) 0.2279(4) 0.0736(10) Uani 1 1 d . . . . .
N4 N -0.1607(4) 0.3866(3) 0.5099(3) 0.0685(9) Uani 1 1 d . . . . .
O1 O 0.9001(3) 0.8250(2) 0.3036(3) 0.0956(11) Uani 1 1 d . . . . .
O2 O 0.9279(4) 0.7580(2) 0.1468(3) 0.1129(13) Uani 1 1 d . . . . .
O3 O -0.2684(4) 0.4407(3) 0.4937(3) 0.0969(10) Uani 1 1 d . . . . .
O4 O -0.1287(4) 0.3347(2) 0.5926(3) 0.1034(11) 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
C1 C6 1.364(4) . ?
C1 C2N 1.371(5) . ?
C1 N3 1.476(5) . ?
C3 C2N 1.383(5) . ?
C3 C4 1.383(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(4) . ?
C4 C7 1.498(4) . ?
C5 C6 1.375(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.470(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N2 1.145(5) . ?
C8 N1 1.329(5) . ?
C9 N1 1.475(4) . ?
C9 C10 1.509(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.384(4) . ?
C10 C11 1.390(4) . ?
C11 C12 1.370(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(5) . ?
C13 N4 1.471(4) . ?
C14 C15 1.378(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C2N H2N 0.9300 . ?
N3 O2 1.216(4) . ?
N3 O1 1.220(4) . ?
N4 O3 1.214(4) . ?
N4 O4 1.213(4) . ?

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 C1 C2N 122.7(3) . . ?
C6 C1 N3 118.7(4) . . ?
C2N C1 N3 118.6(4) . . ?
C2N C3 C4 120.4(3) . . ?
C2N C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 C7 122.2(3) . . ?
C5 C4 C7 118.8(3) . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 118.1(3) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
N1 C7 C4 113.6(3) . . ?
N1 C7 H7A 108.9 . . ?
C4 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C4 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
N2 C8 N1 176.9(4) . . ?
N1 C9 C10 113.2(3) . . ?
N1 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C15 C10 C11 118.5(3) . . ?
C15 C10 C9 120.8(3) . . ?
C11 C10 C9 120.6(3) . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 118.7(3) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C14 C13 C12 121.8(3) . . ?
C14 C13 N4 120.1(3) . . ?
C12 C13 N4 118.1(3) . . ?
C13 C14 C15 118.7(3) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C14 C15 C10 121.1(3) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
C1 C2N C3 118.6(3) . . ?
C1 C2N H2N 120.7 . . ?
C3 C2N H2N 120.7 . . ?
C8 N1 C7 117.6(3) . . ?
C8 N1 C9 117.3(3) . . ?
C7 N1 C9 115.2(3) . . ?
O2 N3 O1 123.7(4) . . ?
O2 N3 C1 118.2(4) . . ?
O1 N3 C1 118.1(4) . . ?
O3 N4 O4 123.9(4) . . ?
O3 N4 C13 117.7(3) . . ?
O4 N4 C13 118.4(4) . . ?

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
C2N C3 C4 C5 0.3(5) . . . . ?
C2N C3 C4 C7 -175.9(3) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
C7 C4 C5 C6 175.6(3) . . . . ?
C2N C1 C6 C5 1.4(5) . . . . ?
N3 C1 C6 C5 -178.9(3) . . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
C3 C4 C7 N1 -40.6(4) . . . . ?
C5 C4 C7 N1 143.2(3) . . . . ?
N1 C9 C10 C15 -117.8(3) . . . . ?
N1 C9 C10 C11 62.5(4) . . . . ?
C15 C10 C11 C12 -0.9(5) . . . . ?
C9 C10 C11 C12 178.8(3) . . . . ?
C10 C11 C12 C13 -0.1(5) . . . . ?
C11 C12 C13 C14 0.5(5) . . . . ?
C11 C12 C13 N4 -177.8(3) . . . . ?
C12 C13 C14 C15 0.2(5) . . . . ?
N4 C13 C14 C15 178.5(3) . . . . ?
C13 C14 C15 C10 -1.3(5) . . . . ?
C11 C10 C15 C14 1.7(5) . . . . ?
C9 C10 C15 C14 -178.1(3) . . . . ?
C6 C1 C2N C3 -1.9(5) . . . . ?
N3 C1 C2N C3 178.5(3) . . . . ?
C4 C3 C2N C1 1.0(5) . . . . ?
C4 C7 N1 C8 -53.4(4) . . . . ?
C4 C7 N1 C9 161.8(3) . . . . ?
C10 C9 N1 C8 -89.5(4) . . . . ?
C10 C9 N1 C7 55.4(4) . . . . ?
C6 C1 N3 O2 -177.0(3) . . . . ?
C2N C1 N3 O2 2.7(5) . . . . ?
C6 C1 N3 O1 3.2(5) . . . . ?
C2N C1 N3 O1 -177.1(3) . . . . ?
C14 C13 N4 O3 -174.1(3) . . . . ?
C12 C13 N4 O3 4.2(5) . . . . ?
C14 C13 N4 O4 7.4(5) . . . . ?
C12 C13 N4 O4 -174.2(3) . . . . ?

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2324490'
loop_
_audit_author_name
_audit_author_address
'Zhongjie Wang'
; College of Chemistry and Chemical Engineering Ningxia University Yinchuan 
China
;
_audit_update_record             
;
2024-01-10 deposited with the CCDC.	2024-07-16 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            'C15 H14 F2 N2 O'
_chemical_formula_weight         276.28

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'
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'
F F 0.0171 0.0103 '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                   11.6329(6)
_cell_length_b                   7.7767(5)
_cell_length_c                   29.3752(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2657.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7250
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      23.45

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27013
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.226
_diffrn_reflns_theta_max         25.036
_diffrn_reflns_theta_full        25.036
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2332
_reflns_number_gt                1743
_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)+(0.0476P)²+1.4536P] 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         2332
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1202
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.034
_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
C1 C 0.59804(19) 0.0455(3) 0.42561(9) 0.0494(6) Uani 1 1 d . U . . .
C2 C 0.6592(2) -0.0136(4) 0.46209(12) 0.0717(9) Uani 1 1 d . . . . .
H2 H 0.7004 -0.1159 0.4602 0.086 Uiso 1 1 calc R U . . .
C3 C 0.6588(3) 0.0806(5) 0.50143(12) 0.0826(11) Uani 1 1 d . . . . .
H3 H 0.6997 0.0428 0.5267 0.099 Uiso 1 1 calc R U . . .
C4 C 0.5980(3) 0.2303(5) 0.50325(9) 0.0789(10) Uani 1 1 d . . . . .
H4 H 0.5973 0.2942 0.5300 0.095 Uiso 1 1 calc R U . . .
C5 C 0.5377(2) 0.2879(4) 0.46593(8) 0.0588(7) Uani 1 1 d . . . . .
H5 H 0.4969 0.3905 0.4678 0.071 Uiso 1 1 calc R U . . .
C6 C 0.53658(17) 0.1962(3) 0.42573(7) 0.0373(5) Uani 1 1 d . . . . .
C7 C 0.46994(18) 0.2534(3) 0.38451(7) 0.0392(5) Uani 1 1 d . . . . .
H7A H 0.5013 0.1975 0.3577 0.047 Uiso 1 1 calc R U . . .
H7B H 0.3906 0.2170 0.3877 0.047 Uiso 1 1 calc R U . . .
C8 C 0.37453(17) 0.5335(3) 0.38018(6) 0.0324(5) Uani 1 1 d . . . . .
C9 C 0.58319(16) 0.5122(3) 0.36434(7) 0.0364(5) Uani 1 1 d . . . . .
H9A H 0.6442 0.4401 0.3763 0.044 Uiso 1 1 calc R U . . .
H9B H 0.5909 0.6247 0.3783 0.044 Uiso 1 1 calc R U . . .
C10 C 0.59972(16) 0.5306(3) 0.31358(7) 0.0341(5) Uani 1 1 d . . . . .
C11 C 0.52358(18) 0.4690(3) 0.28129(8) 0.0420(5) Uani 1 1 d . . . . .
H11 H 0.4552 0.4182 0.2907 0.050 Uiso 1 1 calc R U . . .
C12 C 0.5475(2) 0.4817(3) 0.23534(8) 0.0540(7) Uani 1 1 d . . . . .
H12 H 0.4952 0.4395 0.2142 0.065 Uiso 1 1 calc R U . . .
C13 C 0.6480(2) 0.5563(3) 0.22075(9) 0.0582(7) Uani 1 1 d . . . . .
H13 H 0.6645 0.5622 0.1898 0.070 Uiso 1 1 calc R U . . .
C14 C 0.7240(2) 0.6221(3) 0.25196(9) 0.0565(7) Uani 1 1 d . . . . .
H14 H 0.7916 0.6752 0.2426 0.068 Uiso 1 1 calc R U . . .
C15 C 0.69779(17) 0.6077(3) 0.29722(8) 0.0438(6) Uani 1 1 d . . . . .
F1 F 0.59628(13) -0.05205(18) 0.38698(6) 0.0726(5) Uani 1 1 d . U . . .
F2 F 0.77274(12) 0.6718(2) 0.32852(5) 0.0722(5) Uani 1 1 d . . . . .
N1 N 0.47309(13) 0.4390(2) 0.37786(6) 0.0351(4) Uani 1 1 d . . . . .
N2 N 0.38289(15) 0.7018(2) 0.37059(6) 0.0460(5) Uani 1 1 d . . . . .
H2A H 0.3229 0.7662 0.3718 0.055 Uiso 1 1 calc R U . . .
H2B H 0.4483 0.7453 0.3632 0.055 Uiso 1 1 calc R U . . .
O1 O 0.28168(12) 0.46931(19) 0.39075(5) 0.0475(4) 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
C1 F1 1.365(3) . ?
C1 C2 1.366(4) . ?
C1 C6 1.373(3) . ?
C2 C3 1.368(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.505(3) . ?
C7 N1 1.457(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.230(2) . ?
C8 N2 1.342(3) . ?
C8 N1 1.364(3) . ?
C9 N1 1.457(2) . ?
C9 C10 1.510(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.375(3) . ?
C10 C11 1.383(3) . ?
C11 C12 1.382(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(3) . ?
C14 H14 0.9300 . ?
C15 F2 1.362(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?

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
F1 C1 C2 118.2(2) . . ?
F1 C1 C6 118.0(2) . . ?
C2 C1 C6 123.8(3) . . ?
C1 C2 C3 118.7(3) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 116.0(2) . . ?
C1 C6 C7 121.2(2) . . ?
C5 C6 C7 122.7(2) . . ?
N1 C7 C6 112.82(17) . . ?
N1 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
O1 C8 N2 120.84(19) . . ?
O1 C8 N1 122.13(18) . . ?
N2 C8 N1 117.03(18) . . ?
N1 C9 C10 114.72(16) . . ?
N1 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
N1 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C15 C10 C11 116.3(2) . . ?
C15 C10 C9 119.47(19) . . ?
C11 C10 C9 124.23(18) . . ?
C10 C11 C12 121.1(2) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 118.4(2) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
F2 C15 C14 118.9(2) . . ?
F2 C15 C10 117.0(2) . . ?
C14 C15 C10 124.0(2) . . ?
C8 N1 C9 122.82(17) . . ?
C8 N1 C7 120.42(17) . . ?
C9 N1 C7 116.48(16) . . ?
C8 N2 H2A 120.0 . . ?
C8 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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 -178.1(2) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
F1 C1 C6 C5 177.9(2) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
F1 C1 C6 C7 -0.5(3) . . . . ?
C2 C1 C6 C7 -179.4(2) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
C4 C5 C6 C7 178.9(2) . . . . ?
C1 C6 C7 N1 -143.2(2) . . . . ?
C5 C6 C7 N1 38.5(3) . . . . ?
N1 C9 C10 C15 176.16(18) . . . . ?
N1 C9 C10 C11 -6.2(3) . . . . ?
C15 C10 C11 C12 1.5(3) . . . . ?
C9 C10 C11 C12 -176.2(2) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C14 -1.5(4) . . . . ?
C12 C13 C14 C15 1.4(4) . . . . ?
C13 C14 C15 F2 179.7(2) . . . . ?
C13 C14 C15 C10 0.2(4) . . . . ?
C11 C10 C15 F2 178.85(19) . . . . ?
C9 C10 C15 F2 -3.3(3) . . . . ?
C11 C10 C15 C14 -1.6(3) . . . . ?
C9 C10 C15 C14 176.2(2) . . . . ?
O1 C8 N1 C9 178.49(19) . . . . ?
N2 C8 N1 C9 -1.9(3) . . . . ?
O1 C8 N1 C7 4.8(3) . . . . ?
N2 C8 N1 C7 -175.52(18) . . . . ?
C10 C9 N1 C8 -80.8(2) . . . . ?
C10 C9 N1 C7 93.0(2) . . . . ?
C6 C7 N1 C8 -116.6(2) . . . . ?
C6 C7 N1 C9 69.3(2) . . . . ?

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.036

