# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_5-5-2
_database_code_depnum_ccdc_archive 'CCDC 2105987'
loop_
_audit_author_name
_audit_author_address
cvcv
;fddf
China
;
_audit_update_record             
;
2021-08-27 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_audit_creation_date             2020-09-17
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H18 Br2 N2 O2'
_chemical_formula_sum            'C25 H18 Br2 N2 O2'
_chemical_formula_weight         538.23
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   16.854(2)
_cell_length_b                   22.397(2)
_cell_length_c                   5.6423(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2129.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2756
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.8420
_cell_measurement_theta_min      2.5810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.832
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            12574
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         2.184
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  84.00   1.00    6.50    --   11.90  57.00 -30.00  100
  2  ω     36.00  62.00   1.00    6.50    --   11.90 178.00 150.00   26
  3  ω    -54.00  35.00   1.00    6.50    --   11.90 -57.00-180.00   89
  4  ω    -75.00 -25.00   1.00    6.50    --  -11.27 -77.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0299660000
_diffrn_orient_matrix_UB_12      0.0179023000
_diffrn_orient_matrix_UB_13      0.0524297000
_diffrn_orient_matrix_UB_21      -0.0253645000
_diffrn_orient_matrix_UB_22      -0.0252330000
_diffrn_orient_matrix_UB_23      0.0062955000
_diffrn_orient_matrix_UB_31      0.0152027000
_diffrn_orient_matrix_UB_32      -0.0068032000
_diffrn_orient_matrix_UB_33      0.1140343000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.666
_reflns_Friedel_fraction_full    0.834
_reflns_Friedel_fraction_max     0.834
_reflns_number_gt                2498
_reflns_number_total             3466
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 773 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3466
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0279P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0802
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2B), C2(H2A), C4(H4), C5(H5), C8(H8), C11(H11), C14(H14),
 C15(H15), C17(H17), C21(H21), C22(H22), C23(H23), C24(H24)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.00050(6) 0.55883(4) 1.07211(19) 0.1020(4) Uani 1 1 d . . . . .
Br2 Br 0.54897(5) 0.71142(3) 1.03118(16) 0.0747(3) Uani 1 1 d . . . . .
O1 O 0.6912(3) 0.41619(17) 0.5595(11) 0.0774(15) Uani 1 1 d . . . . .
O2 O 0.6959(3) 0.30126(15) 0.5177(11) 0.0645(12) Uani 1 1 d . . . . .
H2 H 0.680791 0.333217 0.572389 0.097 Uiso 1 1 calc R U . . .
N1 N 0.8247(4) 0.6752(2) 0.2747(11) 0.0603(16) Uani 1 1 d . . . . .
H1 H 0.831819 0.706748 0.190531 0.072 Uiso 1 1 calc R U . . .
N2 N 0.5147(4) 0.5468(3) 0.2077(11) 0.0682(18) Uani 1 1 d . . . . .
H2B H 0.476622 0.537606 0.113195 0.082 Uiso 1 1 calc R U . . .
C1 C 0.8408(3) 0.6031(2) 0.5427(14) 0.0452(14) Uani 1 1 d . . . . .
C2 C 0.8788(4) 0.5736(3) 0.7286(12) 0.0532(18) Uani 1 1 d . . . . .
H2A H 0.858298 0.538245 0.790224 0.064 Uiso 1 1 calc R U . . .
C3 C 0.9475(5) 0.5982(3) 0.8185(13) 0.063(2) Uani 1 1 d . . . . .
C4 C 0.9794(5) 0.6510(4) 0.7322(16) 0.073(2) Uani 1 1 d . . . . .
H4 H 1.025949 0.666328 0.796764 0.088 Uiso 1 1 calc R U . . .
C5 C 0.9420(4) 0.6805(3) 0.551(2) 0.0649(19) Uani 1 1 d . . . . .
H5 H 0.962492 0.716188 0.493986 0.078 Uiso 1 1 calc R U . . .
C6 C 0.8733(4) 0.6568(3) 0.4547(13) 0.0525(19) Uani 1 1 d . . . . .
C7 C 0.7712(4) 0.5908(3) 0.4082(11) 0.0433(16) Uani 1 1 d . . . . .
C8 C 0.7635(4) 0.6361(3) 0.2486(12) 0.0539(18) Uani 1 1 d . . . . .
H8 H 0.722718 0.639723 0.138602 0.065 Uiso 1 1 calc R U . . .
C9 C 0.7199(4) 0.5354(2) 0.4367(11) 0.0483(17) Uani 1 1 d . . . . .
H9 H 0.721267 0.524701 0.605096 0.058 Uiso 1 1 calc R U . . .
C10 C 0.6346(4) 0.5475(3) 0.3755(11) 0.0473(17) Uani 1 1 d . . . . .
C11 C 0.5903(5) 0.5237(3) 0.1949(12) 0.062(2) Uani 1 1 d . . . . .
H11 H 0.608269 0.496523 0.082542 0.074 Uiso 1 1 calc R U . . .
C12 C 0.5842(4) 0.5874(2) 0.4981(12) 0.0409(15) Uani 1 1 d . . . . .
C13 C 0.5085(5) 0.5867(3) 0.3924(13) 0.0520(18) Uani 1 1 d . . . . .
C14 C 0.4464(4) 0.6215(3) 0.4712(16) 0.069(3) Uani 1 1 d . . . . .
H14 H 0.396978 0.619968 0.398153 0.083 Uiso 1 1 calc R U . . .
C15 C 0.4598(4) 0.6579(3) 0.6588(14) 0.064(2) Uani 1 1 d . . . . .
H15 H 0.419114 0.682060 0.714983 0.076 Uiso 1 1 calc R U . . .
C16 C 0.5337(5) 0.6596(3) 0.7686(12) 0.0522(18) Uani 1 1 d . . . . .
C17 C 0.5956(4) 0.6247(3) 0.6923(10) 0.0445(17) Uani 1 1 d . . . . .
H17 H 0.644416 0.625977 0.769227 0.053 Uiso 1 1 calc R U . . .
C18 C 0.7580(4) 0.4832(3) 0.3004(13) 0.060(2) Uani 1 1 d . . . . .
H18A H 0.744622 0.487234 0.133920 0.072 Uiso 1 1 calc R U . . .
H18B H 0.815203 0.486536 0.313950 0.072 Uiso 1 1 calc R U . . .
C19 C 0.7336(4) 0.4216(3) 0.3819(12) 0.0519(19) Uani 1 1 d . . . . .
C20 C 0.7632(4) 0.3692(3) 0.2549(12) 0.0456(16) Uani 1 1 d . . . . .
C21 C 0.8121(4) 0.3753(3) 0.0553(16) 0.0586(17) Uani 1 1 d . . . . .
H21 H 0.826544 0.413197 0.003666 0.070 Uiso 1 1 calc R U . . .
C22 C 0.8389(4) 0.3260(3) -0.0648(13) 0.070(2) Uani 1 1 d . . . . .
H22 H 0.872509 0.330365 -0.194442 0.084 Uiso 1 1 calc R U . . .
C23 C 0.8159(4) 0.2700(3) 0.0078(18) 0.072(2) Uani 1 1 d . . . . .
H23 H 0.833119 0.236635 -0.075909 0.086 Uiso 1 1 calc R U . . .
C24 C 0.7685(4) 0.2627(3) 0.1994(14) 0.062(2) Uani 1 1 d . . . . .
H24 H 0.753576 0.224513 0.246489 0.075 Uiso 1 1 calc R U . . .
C25 C 0.7425(4) 0.3115(3) 0.3244(12) 0.0469(17) 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
Br1 C3 1.904(7) . ?
Br2 C16 1.900(7) . ?
O1 C19 1.237(8) . ?
O2 H2 0.8200 . ?
O2 C25 1.364(8) . ?
N1 H1 0.8600 . ?
N1 C6 1.368(9) . ?
N1 C8 1.361(8) . ?
N2 H2B 0.8600 . ?
N2 C11 1.376(9) . ?
N2 C13 1.377(9) . ?
C1 C2 1.396(10) . ?
C1 C6 1.412(8) . ?
C1 C7 1.424(8) . ?
C2 H2A 0.9300 . ?
C2 C3 1.380(9) . ?
C3 C4 1.388(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.369(13) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(10) . ?
C7 C8 1.363(8) . ?
C7 C9 1.520(8) . ?
C8 H8 0.9300 . ?
C9 H9 0.9800 . ?
C9 C10 1.503(9) . ?
C9 C18 1.540(8) . ?
C10 C11 1.372(9) . ?
C10 C12 1.414(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.408(9) . ?
C12 C17 1.391(8) . ?
C13 C14 1.378(10) . ?
C14 H14 0.9300 . ?
C14 C15 1.355(10) . ?
C15 H15 0.9300 . ?
C15 C16 1.391(9) . ?
C16 C17 1.372(9) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.511(9) . ?
C19 C20 1.463(9) . ?
C20 C21 1.402(10) . ?
C20 C25 1.395(8) . ?
C21 H21 0.9300 . ?
C21 C22 1.373(9) . ?
C22 H22 0.9300 . ?
C22 C23 1.375(10) . ?
C23 H23 0.9300 . ?
C23 C24 1.354(11) . ?
C24 H24 0.9300 . ?
C24 C25 1.373(9) . ?

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
C25 O2 H2 109.5 . . ?
C6 N1 H1 125.0 . . ?
C8 N1 H1 125.0 . . ?
C8 N1 C6 109.9(6) . . ?
C11 N2 H2B 124.6 . . ?
C11 N2 C13 110.7(6) . . ?
C13 N2 H2B 124.6 . . ?
C2 C1 C6 119.4(6) . . ?
C2 C1 C7 133.3(6) . . ?
C6 C1 C7 107.3(6) . . ?
C1 C2 H2A 121.0 . . ?
C3 C2 C1 118.1(6) . . ?
C3 C2 H2A 121.0 . . ?
C2 C3 Br1 119.0(6) . . ?
C2 C3 C4 122.6(7) . . ?
C4 C3 Br1 118.5(7) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.5(7) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.7(7) . . ?
C6 C5 H5 120.2 . . ?
N1 C6 C1 106.6(6) . . ?
N1 C6 C5 132.7(7) . . ?
C5 C6 C1 120.8(7) . . ?
C1 C7 C9 124.8(6) . . ?
C8 C7 C1 106.6(6) . . ?
C8 C7 C9 128.6(6) . . ?
N1 C8 C7 109.6(6) . . ?
N1 C8 H8 125.2 . . ?
C7 C8 H8 125.2 . . ?
C7 C9 H9 106.8 . . ?
C7 C9 C18 109.3(5) . . ?
C10 C9 C7 111.8(5) . . ?
C10 C9 H9 106.8 . . ?
C10 C9 C18 114.9(5) . . ?
C18 C9 H9 106.8 . . ?
C11 C10 C9 128.4(7) . . ?
C11 C10 C12 106.4(7) . . ?
C12 C10 C9 125.2(6) . . ?
N2 C11 H11 125.7 . . ?
C10 C11 N2 108.6(7) . . ?
C10 C11 H11 125.7 . . ?
C13 C12 C10 109.3(6) . . ?
C17 C12 C10 133.0(6) . . ?
C17 C12 C13 117.8(6) . . ?
N2 C13 C12 105.0(7) . . ?
N2 C13 C14 131.9(7) . . ?
C14 C13 C12 123.0(7) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 C13 117.7(7) . . ?
C15 C14 H14 121.2 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.9(7) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 Br2 119.0(6) . . ?
C17 C16 Br2 119.3(6) . . ?
C17 C16 C15 121.7(7) . . ?
C12 C17 H17 120.6 . . ?
C16 C17 C12 118.9(6) . . ?
C16 C17 H17 120.6 . . ?
C9 C18 H18A 108.4 . . ?
C9 C18 H18B 108.4 . . ?
H18A C18 H18B 107.5 . . ?
C19 C18 C9 115.3(6) . . ?
C19 C18 H18A 108.4 . . ?
C19 C18 H18B 108.4 . . ?
O1 C19 C18 119.6(6) . . ?
O1 C19 C20 121.0(6) . . ?
C20 C19 C18 119.4(6) . . ?
C21 C20 C19 121.1(6) . . ?
C25 C20 C19 121.4(6) . . ?
C25 C20 C21 117.5(6) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.8(6) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.6(7) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 121.0(7) . . ?
C24 C23 H23 119.5 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.2(7) . . ?
C25 C24 H24 119.9 . . ?
O2 C25 C20 121.6(6) . . ?
O2 C25 C24 117.4(6) . . ?
C24 C25 C20 120.9(7) . . ?

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
Br1 C3 C4 C5 -179.4(6) . . . . ?
Br2 C16 C17 C12 -179.2(4) . . . . ?
O1 C19 C20 C21 -179.2(7) . . . . ?
O1 C19 C20 C25 2.2(10) . . . . ?
N2 C13 C14 C15 -178.6(7) . . . . ?
C1 C2 C3 Br1 -180.0(5) . . . . ?
C1 C2 C3 C4 0.5(10) . . . . ?
C1 C7 C8 N1 0.7(7) . . . . ?
C1 C7 C9 C10 150.4(6) . . . . ?
C1 C7 C9 C18 -81.3(8) . . . . ?
C2 C1 C6 N1 179.5(6) . . . . ?
C2 C1 C6 C5 -0.3(10) . . . . ?
C2 C1 C7 C8 180.0(7) . . . . ?
C2 C1 C7 C9 -2.8(11) . . . . ?
C2 C3 C4 C5 0.2(12) . . . . ?
C3 C4 C5 C6 -0.9(13) . . . . ?
C4 C5 C6 N1 -178.8(8) . . . . ?
C4 C5 C6 C1 1.0(12) . . . . ?
C6 N1 C8 C7 -0.9(7) . . . . ?
C6 C1 C2 C3 -0.4(9) . . . . ?
C6 C1 C7 C8 -0.3(7) . . . . ?
C6 C1 C7 C9 176.9(6) . . . . ?
C7 C1 C2 C3 179.3(7) . . . . ?
C7 C1 C6 N1 -0.2(7) . . . . ?
C7 C1 C6 C5 179.9(6) . . . . ?
C7 C9 C10 C11 115.9(7) . . . . ?
C7 C9 C10 C12 -63.7(8) . . . . ?
C7 C9 C18 C19 157.9(6) . . . . ?
C8 N1 C6 C1 0.7(7) . . . . ?
C8 N1 C6 C5 -179.5(8) . . . . ?
C8 C7 C9 C10 -33.0(9) . . . . ?
C8 C7 C9 C18 95.4(8) . . . . ?
C9 C7 C8 N1 -176.4(6) . . . . ?
C9 C10 C11 N2 179.1(6) . . . . ?
C9 C10 C12 C13 -179.4(6) . . . . ?
C9 C10 C12 C17 0.5(10) . . . . ?
C9 C18 C19 O1 -5.8(10) . . . . ?
C9 C18 C19 C20 176.7(6) . . . . ?
C10 C9 C18 C19 -75.5(8) . . . . ?
C10 C12 C13 N2 -0.3(7) . . . . ?
C10 C12 C13 C14 -179.5(6) . . . . ?
C10 C12 C17 C16 178.9(6) . . . . ?
C11 N2 C13 C12 -0.5(7) . . . . ?
C11 N2 C13 C14 178.5(7) . . . . ?
C11 C10 C12 C13 1.0(7) . . . . ?
C11 C10 C12 C17 -179.1(6) . . . . ?
C12 C10 C11 N2 -1.3(7) . . . . ?
C12 C13 C14 C15 0.2(10) . . . . ?
C13 N2 C11 C10 1.2(8) . . . . ?
C13 C12 C17 C16 -1.2(8) . . . . ?
C13 C14 C15 C16 -0.5(10) . . . . ?
C14 C15 C16 Br2 -179.9(5) . . . . ?
C14 C15 C16 C17 0.0(10) . . . . ?
C15 C16 C17 C12 0.9(9) . . . . ?
C17 C12 C13 N2 179.7(5) . . . . ?
C17 C12 C13 C14 0.6(9) . . . . ?
C18 C9 C10 C11 -9.4(9) . . . . ?
C18 C9 C10 C12 171.1(6) . . . . ?
C18 C19 C20 C21 -1.7(10) . . . . ?
C18 C19 C20 C25 179.7(6) . . . . ?
C19 C20 C21 C22 -179.2(6) . . . . ?
C19 C20 C25 O2 -2.1(9) . . . . ?
C19 C20 C25 C24 177.9(6) . . . . ?
C20 C21 C22 C23 1.7(12) . . . . ?
C21 C20 C25 O2 179.3(6) . . . . ?
C21 C20 C25 C24 -0.8(10) . . . . ?
C21 C22 C23 C24 -1.5(12) . . . . ?
C22 C23 C24 C25 0.2(12) . . . . ?
C23 C24 C25 O2 -179.0(7) . . . . ?
C23 C24 C25 C20 1.0(11) . . . . ?
C25 C20 C21 C22 -0.6(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.836
_oxdiff_exptl_absorpt_empirical_full_min 0.680
####################################################################### 
# 
# 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_wjx-5-14
_database_code_depnum_ccdc_archive 'CCDC 2105989'
loop_
_audit_author_name
_audit_author_address
xcv
;wddaw
China
;
_audit_update_record             
;
2021-08-27 deposited with the CCDC.	2021-12-06 downloaded from the CCDC.
;
_audit_creation_date             2020-09-17
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H18 F2 N2 O2'
_chemical_formula_sum            'C25 H18 F2 N2 O2'
_chemical_formula_weight         416.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.269(3)
_cell_length_b                   8.445(2)
_cell_length_c                   20.524(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.54(2)
_cell_angle_gamma                90
_cell_volume                     1940.5(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2666
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.9550
_cell_measurement_theta_min      2.5480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8553
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         1.998
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  27.00   1.00    4.50    --  -11.27 -99.00 -30.00   36
  2  ω      1.00  80.00   1.00    4.50    --   11.90  37.00 -30.00   79
  3  ω     -6.00  90.00   1.00    4.50    --   11.90  19.00-120.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0566213000
_diffrn_orient_matrix_UB_12      -0.0375517000
_diffrn_orient_matrix_UB_13      0.0058627000
_diffrn_orient_matrix_UB_21      0.0279528000
_diffrn_orient_matrix_UB_22      0.0712509000
_diffrn_orient_matrix_UB_23      -0.0081728000
_diffrn_orient_matrix_UB_31      0.0045074000
_diffrn_orient_matrix_UB_32      0.0239114000
_diffrn_orient_matrix_UB_33      0.0333232000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2251
_reflns_number_total             3412
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3412
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0604
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0862P)²+0.0855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1842
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid bond restraints
 C12, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C12 \\sim C17: within 1.7A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 1.7A
4.a Ternary CH refined with riding coordinates:
 C9(H9)
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2A), C2(H2B), C4(H4), C5(H5), C7(H7), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C22(H22), C23(H23), C25(H25)
4.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.79000(19) 0.2135(3) 0.50803(10) 0.0907(7) Uani 1 1 d . . . . .
F2 F 0.98636(16) 0.9966(2) 0.67747(9) 0.0825(7) Uani 1 1 d . . . . .
O1 O 0.57139(19) 0.9885(3) 0.35203(9) 0.0675(6) Uani 1 1 d . . . . .
O2 O 0.46452(17) 1.0098(3) 0.23577(8) 0.0609(6) Uani 1 1 d . . . . .
H2 H 0.512981 1.034271 0.267011 0.091 Uiso 1 1 calc R U . . .
N1 N 0.9060(2) 0.7613(3) 0.39476(11) 0.0615(7) Uani 1 1 d . . . . .
H1 H 0.962372 0.789590 0.372340 0.074 Uiso 1 1 calc R U . . .
N2 N 0.5760(2) 0.6648(3) 0.63314(10) 0.0586(7) Uani 1 1 d . . . . .
H2A H 0.535377 0.607931 0.657404 0.070 Uiso 1 1 calc R U . . .
C1 C 0.7879(2) 0.6194(4) 0.45242(10) 0.0484(7) Uani 1 1 d . . . . .
C2 C 0.7554(2) 0.4808(4) 0.48314(12) 0.0520(7) Uani 1 1 d . . . . .
H2B H 0.689927 0.479138 0.506941 0.062 Uiso 1 1 calc R U . . .
C3 C 0.8215(3) 0.3497(4) 0.47731(13) 0.0623(8) Uani 1 1 d . . . . .
C4 C 0.9202(3) 0.3416(4) 0.44334(14) 0.0645(9) Uani 1 1 d . . . . .
H4 H 0.961372 0.246853 0.440505 0.077 Uiso 1 1 calc R U . . .
C5 C 0.9563(3) 0.4765(4) 0.41380(13) 0.0637(9) Uani 1 1 d . . . . .
H5 H 1.023483 0.475920 0.391389 0.076 Uiso 1 1 calc R U . . .
C6 C 0.8903(2) 0.6124(4) 0.41822(11) 0.0509(7) Uani 1 1 d . . . . .
C7 C 0.8184(3) 0.8578(4) 0.41238(12) 0.0602(8) Uani 1 1 d . . . . .
H7 H 0.810852 0.964687 0.401747 0.072 Uiso 1 1 calc R U . . .
C8 C 0.7435(2) 0.7767(4) 0.44761(11) 0.0500(7) Uani 1 1 d . . . . .
C9 C 0.6343(2) 0.8441(4) 0.47456(11) 0.0537(7) Uani 1 1 d . . . . .
H9 H 0.642228 0.959613 0.475312 0.064 Uiso 1 1 calc R U . . .
C10 C 0.5193(2) 0.8038(4) 0.43197(12) 0.0597(8) Uani 1 1 d . . . . .
H10A H 0.516864 0.690143 0.425021 0.072 Uiso 1 1 calc R U . . .
H10B H 0.452703 0.831206 0.455820 0.072 Uiso 1 1 calc R U . . .
C11 C 0.5016(3) 0.8844(4) 0.36582(12) 0.0559(8) Uani 1 1 d . . . . .
C12 C 0.4012(2) 0.8379(4) 0.31865(12) 0.0521(7) Uani 1 1 d . U . . .
C13 C 0.3872(2) 0.9014(4) 0.25521(12) 0.0531(7) Uani 1 1 d . . . . .
C14 C 0.2940(3) 0.8551(4) 0.20947(14) 0.0687(9) Uani 1 1 d . . . . .
H14 H 0.286318 0.898665 0.167580 0.082 Uiso 1 1 calc R U . . .
C15 C 0.2136(3) 0.7463(5) 0.22556(15) 0.0746(10) Uani 1 1 d . . . . .
H15 H 0.151586 0.714644 0.194515 0.090 Uiso 1 1 calc R U . . .
C16 C 0.2236(3) 0.6832(4) 0.28720(15) 0.0690(9) Uani 1 1 d . . . . .
H16 H 0.167586 0.609451 0.297823 0.083 Uiso 1 1 calc R U . . .
C17 C 0.3147(3) 0.7266(4) 0.33358(13) 0.0591(7) Uani 1 1 d . U . . .
H17 H 0.319738 0.682462 0.375318 0.071 Uiso 1 1 calc R U . . .
C18 C 0.6293(2) 0.7892(4) 0.54439(12) 0.0509(7) Uani 1 1 d . . . . .
C19 C 0.5449(3) 0.6964(4) 0.56812(13) 0.0594(8) Uani 1 1 d . . . . .
H19 H 0.475974 0.659900 0.543520 0.071 Uiso 1 1 calc R U . . .
C20 C 0.7186(2) 0.8172(3) 0.59845(11) 0.0456(7) Uani 1 1 d . . . . .
C21 C 0.6816(2) 0.7377(3) 0.65328(12) 0.0490(7) Uani 1 1 d . . . . .
C22 C 0.7472(3) 0.7431(4) 0.71448(13) 0.0573(8) Uani 1 1 d . . . . .
H22 H 0.722071 0.688985 0.749910 0.069 Uiso 1 1 calc R U . . .
C23 C 0.8494(3) 0.8298(4) 0.72128(13) 0.0613(8) Uani 1 1 d . . . . .
H23 H 0.895724 0.836348 0.761699 0.074 Uiso 1 1 calc R U . . .
C24 C 0.8836(2) 0.9080(4) 0.66742(13) 0.0580(8) Uani 1 1 d . . . . .
C25 C 0.8234(2) 0.9045(4) 0.60630(12) 0.0523(7) Uani 1 1 d . . . . .
H25 H 0.851034 0.957998 0.571418 0.063 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.378(4) . ?
F2 C24 1.374(3) . ?
O1 C11 1.234(3) . ?
O2 H2 0.8200 . ?
O2 C13 1.355(3) . ?
N1 H1 0.8600 . ?
N1 C6 1.365(4) . ?
N1 C7 1.361(4) . ?
N2 H2A 0.8600 . ?
N2 C19 1.367(3) . ?
N2 C21 1.362(3) . ?
C1 C2 1.397(4) . ?
C1 C6 1.419(4) . ?
C1 C8 1.419(4) . ?
C2 H2B 0.9300 . ?
C2 C3 1.347(4) . ?
C3 C4 1.380(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.358(4) . ?
C8 C9 1.516(4) . ?
C9 H9 0.9800 . ?
C9 C10 1.517(4) . ?
C9 C18 1.513(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.512(4) . ?
C11 C12 1.456(4) . ?
C12 C13 1.400(4) . ?
C12 C17 1.413(4) . ?
C13 C14 1.384(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.357(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.366(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.368(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.364(4) . ?
C18 C20 1.430(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.413(3) . ?
C20 C25 1.386(4) . ?
C21 C22 1.384(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.358(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.380(4) . ?
C24 C25 1.357(4) . ?
C25 H25 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
C13 O2 H2 109.5 . . ?
C6 N1 H1 125.3 . . ?
C7 N1 H1 125.3 . . ?
C7 N1 C6 109.4(2) . . ?
C19 N2 H2A 125.5 . . ?
C21 N2 H2A 125.5 . . ?
C21 N2 C19 109.0(2) . . ?
C2 C1 C6 117.3(3) . . ?
C2 C1 C8 135.0(3) . . ?
C8 C1 C6 107.7(3) . . ?
C1 C2 H2B 120.9 . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 H2B 120.9 . . ?
F1 C3 C4 117.0(3) . . ?
C2 C3 F1 118.1(3) . . ?
C2 C3 C4 124.8(3) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.3(3) . . ?
C6 C5 H5 120.9 . . ?
N1 C6 C1 106.4(3) . . ?
N1 C6 C5 130.8(3) . . ?
C5 C6 C1 122.9(3) . . ?
N1 C7 H7 124.7 . . ?
C8 C7 N1 110.7(3) . . ?
C8 C7 H7 124.7 . . ?
C1 C8 C9 128.3(2) . . ?
C7 C8 C1 105.9(3) . . ?
C7 C8 C9 125.8(3) . . ?
C8 C9 H9 107.6 . . ?
C10 C9 C8 112.4(2) . . ?
C10 C9 H9 107.6 . . ?
C18 C9 C8 110.5(2) . . ?
C18 C9 H9 107.6 . . ?
C18 C9 C10 110.9(2) . . ?
C9 C10 H10A 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.4 . . ?
C11 C10 C9 115.7(3) . . ?
C11 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
O1 C11 C10 120.3(3) . . ?
O1 C11 C12 120.4(2) . . ?
C12 C11 C10 119.3(3) . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 C17 116.7(3) . . ?
C17 C12 C11 122.5(2) . . ?
O2 C13 C12 121.6(3) . . ?
O2 C13 C14 117.1(3) . . ?
C14 C13 C12 121.3(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C9 128.1(2) . . ?
C19 C18 C20 106.0(2) . . ?
C20 C18 C9 125.8(2) . . ?
N2 C19 H19 124.8 . . ?
C18 C19 N2 110.5(2) . . ?
C18 C19 H19 124.8 . . ?
C21 C20 C18 107.1(2) . . ?
C25 C20 C18 133.9(2) . . ?
C25 C20 C21 119.0(2) . . ?
N2 C21 C20 107.5(2) . . ?
N2 C21 C22 130.4(2) . . ?
C22 C21 C20 122.1(3) . . ?
C21 C22 H22 121.0 . . ?
C23 C22 C21 118.0(2) . . ?
C23 C22 H22 121.0 . . ?
C22 C23 H23 120.4 . . ?
C22 C23 C24 119.1(3) . . ?
C24 C23 H23 120.4 . . ?
F2 C24 C23 116.6(2) . . ?
C25 C24 F2 118.4(2) . . ?
C25 C24 C23 125.1(3) . . ?
C20 C25 H25 121.7 . . ?
C24 C25 C20 116.7(2) . . ?
C24 C25 H25 121.7 . . ?

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 C3 C4 C5 -178.1(2) . . . . ?
F2 C24 C25 C20 -178.4(3) . . . . ?
O1 C11 C12 C13 4.9(4) . . . . ?
O1 C11 C12 C17 -175.9(3) . . . . ?
O2 C13 C14 C15 179.7(3) . . . . ?
N1 C7 C8 C1 0.3(3) . . . . ?
N1 C7 C8 C9 -178.8(2) . . . . ?
N2 C21 C22 C23 -178.1(3) . . . . ?
C1 C2 C3 F1 179.5(2) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C1 C8 C9 C10 -79.3(3) . . . . ?
C1 C8 C9 C18 45.1(4) . . . . ?
C2 C1 C6 N1 -178.0(2) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C2 C1 C8 C7 177.7(3) . . . . ?
C2 C1 C8 C9 -3.3(4) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
C4 C5 C6 N1 179.1(3) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C6 N1 C7 C8 0.1(3) . . . . ?
C6 C1 C2 C3 -1.3(3) . . . . ?
C6 C1 C8 C7 -0.5(3) . . . . ?
C6 C1 C8 C9 178.6(2) . . . . ?
C7 N1 C6 C1 -0.4(3) . . . . ?
C7 N1 C6 C5 -179.0(3) . . . . ?
C7 C8 C9 C10 99.6(3) . . . . ?
C7 C8 C9 C18 -136.0(3) . . . . ?
C8 C1 C2 C3 -179.3(3) . . . . ?
C8 C1 C6 N1 0.6(3) . . . . ?
C8 C1 C6 C5 179.3(2) . . . . ?
C8 C9 C10 C11 -69.3(3) . . . . ?
C8 C9 C18 C19 -116.3(3) . . . . ?
C8 C9 C18 C20 59.3(4) . . . . ?
C9 C10 C11 O1 -7.6(4) . . . . ?
C9 C10 C11 C12 172.5(3) . . . . ?
C9 C18 C19 N2 176.1(3) . . . . ?
C9 C18 C20 C21 -176.5(3) . . . . ?
C9 C18 C20 C25 5.7(5) . . . . ?
C10 C9 C18 C19 9.0(4) . . . . ?
C10 C9 C18 C20 -175.5(3) . . . . ?
C10 C11 C12 C13 -175.1(3) . . . . ?
C10 C11 C12 C17 4.0(4) . . . . ?
C11 C12 C13 O2 -1.3(4) . . . . ?
C11 C12 C13 C14 178.3(3) . . . . ?
C11 C12 C17 C16 -178.2(3) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C13 C12 C17 C16 0.9(4) . . . . ?
C13 C14 C15 C16 0.7(5) . . . . ?
C14 C15 C16 C17 -0.6(5) . . . . ?
C15 C16 C17 C12 -0.2(5) . . . . ?
C17 C12 C13 O2 179.6(3) . . . . ?
C17 C12 C13 C14 -0.9(4) . . . . ?
C18 C9 C10 C11 166.5(3) . . . . ?
C18 C20 C21 N2 0.4(3) . . . . ?
C18 C20 C21 C22 -178.8(3) . . . . ?
C18 C20 C25 C24 177.2(3) . . . . ?
C19 N2 C21 C20 -0.5(3) . . . . ?
C19 N2 C21 C22 178.6(3) . . . . ?
C19 C18 C20 C21 -0.1(3) . . . . ?
C19 C18 C20 C25 -178.0(3) . . . . ?
C20 C18 C19 N2 -0.2(3) . . . . ?
C20 C21 C22 C23 0.8(4) . . . . ?
C21 N2 C19 C18 0.4(3) . . . . ?
C21 C20 C25 C24 -0.4(4) . . . . ?
C21 C22 C23 C24 -0.1(5) . . . . ?
C22 C23 C24 F2 178.7(3) . . . . ?
C22 C23 C24 C25 -0.9(5) . . . . ?
C23 C24 C25 C20 1.1(5) . . . . ?
C25 C20 C21 N2 178.6(2) . . . . ?
C25 C20 C21 C22 -0.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 6.823
_oxdiff_exptl_absorpt_empirical_full_min 0.417
