# 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_exp_809
_audit_block_doi                 10.5517/ccdc.csd.cc1z0tqj
_database_code_depnum_ccdc_archive 'CCDC 1818048'
loop_
_audit_author_name
_audit_author_address
'The Cambridge Crystallographic Data Centre'
'The Cambridge Crystallographic Data Centre'
_audit_update_record             
;
2018-01-19 deposited with the CCDC.	2022-09-28 downloaded from the CCDC.
;
_audit_creation_date             2017-08-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H18 Cl N3 O4'
_chemical_formula_sum            'C25 H18 Cl N3 O4'
_chemical_formula_weight         459.87
_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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5127(4)
_cell_length_b                   9.5403(5)
_cell_length_c                   14.8625(7)
_cell_angle_alpha                95.201(4)
_cell_angle_beta                 95.657(4)
_cell_angle_gamma                92.809(4)
_cell_volume                     1053.89(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3396
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.9420
_cell_measurement_theta_min      4.1970
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84733
_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            colorless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8667
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.572
_diffrn_reflns_theta_min         3.571
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  56.00   1.00    2.00    --  -11.59  57.00   0.00   90
  2  ω    -19.00   6.00   1.00    2.00    --   11.74 -99.00 150.00   25
  3  ω    -77.00  17.00   1.00    2.00    --  -11.59 -77.00  90.00   94
  4  ω    -82.00  16.00   1.00    2.00    --  -11.59 -57.00-150.00   98
;
_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      -0.0731521000
_diffrn_orient_matrix_UB_12      -0.0437356000
_diffrn_orient_matrix_UB_13      0.0100023000
_diffrn_orient_matrix_UB_21      0.0265443000
_diffrn_orient_matrix_UB_22      0.0156035000
_diffrn_orient_matrix_UB_23      0.0471237000
_diffrn_orient_matrix_UB_31      -0.0545554000
_diffrn_orient_matrix_UB_32      0.0586194000
_diffrn_orient_matrix_UB_33      0.0008243000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3921
_reflns_number_total             4943
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4943
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0457
_refine_ls_restrained_S_all      1.024
_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)+(0.0360P)²+0.2826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1024
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C4(H4), C3(H3), C19(H19), C13(H13), C22(H22), C5(H5), C2(H2),
 C16(H16), C15(H15), C21(H21), C20(H20), C14(H14)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.73653(6) 0.11049(5) 0.90426(3) 0.02160(12) Uani 1 1 d . . . . .
O1 O 0.60588(16) 0.13728(12) 0.70347(8) 0.0192(3) Uani 1 1 d . . . . .
O2 O 0.49299(18) 0.69512(13) 0.73029(8) 0.0254(3) Uani 1 1 d . . . . .
O3 O 0.76780(17) 0.37075(13) 0.48620(9) 0.0252(3) Uani 1 1 d . . . . .
O4 O 0.74846(17) 0.15676(14) 0.42215(9) 0.0270(3) Uani 1 1 d . . . . .
N1 N 0.89568(19) 0.23186(14) 0.74703(9) 0.0157(3) Uani 1 1 d . . . . .
N3 N 0.6845(2) 0.25649(16) 0.46331(10) 0.0194(3) Uani 1 1 d . . . . .
N2 N 0.99604(19) 0.36014(14) 0.74135(9) 0.0160(3) Uani 1 1 d . . . . .
C7 C 0.7195(2) 0.23417(17) 0.71177(11) 0.0144(3) Uani 1 1 d . . . . .
C6 C 0.9840(2) 0.11691(17) 0.78192(11) 0.0152(4) Uani 1 1 d . . . . .
C12 C 0.6094(2) 0.60945(18) 0.86786(11) 0.0165(4) Uani 1 1 d . . . . .
C11 C 0.5310(2) 0.44931(17) 0.71955(11) 0.0156(4) Uani 1 1 d . . . . .
H11 H 0.442485 0.382742 0.739107 0.019 Uiso 1 1 calc R . . . .
C9 C 0.8859(2) 0.44788(17) 0.70931(11) 0.0153(4) Uani 1 1 d . . . . .
C8 C 0.7028(2) 0.38282(17) 0.69074(11) 0.0143(3) Uani 1 1 d . . . . .
C25 C 0.5414(2) 0.59500(18) 0.76954(12) 0.0167(4) Uani 1 1 d . . . . .
C17 C 0.6827(2) 0.49761(19) 0.90997(12) 0.0201(4) Uani 1 1 d . . . . .
H17 H 0.688031 0.410736 0.876785 0.024 Uiso 1 1 calc R . . . .
C1 C 0.9181(2) 0.04806(18) 0.85160(12) 0.0173(4) Uani 1 1 d . . . . .
C4 C 1.2269(2) -0.03899(18) 0.78117(12) 0.0196(4) Uani 1 1 d . . . . .
H4 H 1.332430 -0.066695 0.758905 0.024 Uiso 1 1 calc R . . . .
C10 C 0.5574(2) 0.42844(17) 0.62164(11) 0.0154(4) Uani 1 1 d . . . . .
H10 H 0.589182 0.515054 0.594653 0.018 Uiso 1 1 calc R . . . .
C23 C 0.5006(2) 0.23885(17) 0.48654(11) 0.0168(4) Uani 1 1 d . . . . .
C3 C 1.1557(2) -0.10961(18) 0.84787(12) 0.0200(4) Uani 1 1 d . . . . .
H3 H 1.211815 -0.186862 0.868930 0.024 Uiso 1 1 calc R . . . .
C19 C 0.2629(2) 0.30058(19) 0.57274(12) 0.0197(4) Uani 1 1 d . . . . .
H19 H 0.218232 0.354557 0.619789 0.024 Uiso 1 1 calc R . . . .
C18 C 0.4416(2) 0.32132(17) 0.55891(11) 0.0156(4) Uani 1 1 d . . . . .
C13 C 0.6011(2) 0.73953(18) 0.91836(12) 0.0190(4) Uani 1 1 d . . . . .
H13 H 0.553418 0.814979 0.890725 0.023 Uiso 1 1 calc R . . . .
C22 C 0.3889(2) 0.13773(18) 0.43194(12) 0.0213(4) Uani 1 1 d . . . . .
H22 H 0.433084 0.082807 0.385162 0.026 Uiso 1 1 calc R . . . .
C5 C 1.1401(2) 0.07328(18) 0.74763(12) 0.0191(4) Uani 1 1 d . . . . .
H5 H 1.186534 0.119704 0.701951 0.023 Uiso 1 1 calc R . . . .
C24 C 0.9481(2) 0.59167(18) 0.69049(13) 0.0222(4) Uani 1 1 d . . . . .
H24A H 1.073986 0.606798 0.709485 0.033 Uiso 1 1 calc GR . . . .
H24B H 0.883734 0.660467 0.723280 0.033 Uiso 1 1 calc GR . . . .
H24C H 0.926737 0.600583 0.626567 0.033 Uiso 1 1 calc GR . . . .
C2 C 1.0018(2) -0.06639(18) 0.88361(12) 0.0197(4) Uani 1 1 d . . . . .
H2 H 0.954973 -0.113875 0.928754 0.024 Uiso 1 1 calc R . . . .
C16 C 0.7477(3) 0.5154(2) 1.00118(12) 0.0235(4) Uani 1 1 d . . . . .
H16 H 0.797735 0.440897 1.028858 0.028 Uiso 1 1 calc R . . . .
C15 C 0.7379(3) 0.6442(2) 1.05098(12) 0.0247(4) Uani 1 1 d . . . . .
H15 H 0.780962 0.655881 1.112196 0.030 Uiso 1 1 calc R . . . .
C21 C 0.2127(3) 0.1200(2) 0.44793(13) 0.0249(4) Uani 1 1 d . . . . .
H21 H 0.136357 0.053456 0.411583 0.030 Uiso 1 1 calc R . . . .
C20 C 0.1489(3) 0.2017(2) 0.51849(13) 0.0240(4) Uani 1 1 d . . . . .
H20 H 0.029504 0.190148 0.529384 0.029 Uiso 1 1 calc R . . . .
C14 C 0.6642(2) 0.7556(2) 1.00983(12) 0.0228(4) Uani 1 1 d . . . . .
H14 H 0.656979 0.841648 1.043707 0.027 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7415(17) . ?
O1 C7 1.217(2) . ?
O2 C25 1.216(2) . ?
O3 N3 1.2327(18) . ?
O4 N3 1.2279(18) . ?
N1 N2 1.4192(19) . ?
N1 C7 1.376(2) . ?
N1 C6 1.421(2) . ?
N3 C23 1.462(2) . ?
N2 C9 1.294(2) . ?
C7 C8 1.488(2) . ?
C6 C1 1.393(2) . ?
C6 C5 1.391(2) . ?
C12 C25 1.492(2) . ?
C12 C17 1.394(2) . ?
C12 C13 1.398(2) . ?
C11 H11 0.9800 . ?
C11 C8 1.546(2) . ?
C11 C25 1.510(2) . ?
C11 C10 1.485(2) . ?
C9 C8 1.471(2) . ?
C9 C24 1.487(2) . ?
C8 C10 1.531(2) . ?
C17 H17 0.9300 . ?
C17 C16 1.387(2) . ?
C1 C2 1.384(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.383(3) . ?
C4 C5 1.386(2) . ?
C10 H10 0.9800 . ?
C10 C18 1.500(2) . ?
C23 C18 1.395(2) . ?
C23 C22 1.392(2) . ?
C3 H3 0.9300 . ?
C3 C2 1.385(2) . ?
C19 H19 0.9300 . ?
C19 C18 1.385(2) . ?
C19 C20 1.386(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.373(3) . ?
C5 H5 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C2 H2 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.384(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.386(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.387(3) . ?
C20 H20 0.9300 . ?
C14 H14 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
N2 N1 C6 119.21(13) . . ?
C7 N1 N2 112.95(14) . . ?
C7 N1 C6 127.74(14) . . ?
O3 N3 C23 118.34(13) . . ?
O4 N3 O3 123.24(15) . . ?
O4 N3 C23 118.43(14) . . ?
C9 N2 N1 107.33(14) . . ?
O1 C7 N1 127.15(16) . . ?
O1 C7 C8 129.41(15) . . ?
N1 C7 C8 103.40(14) . . ?
C1 C6 N1 120.85(15) . . ?
C5 C6 N1 120.03(16) . . ?
C5 C6 C1 119.11(16) . . ?
C17 C12 C25 121.76(15) . . ?
C17 C12 C13 119.51(16) . . ?
C13 C12 C25 118.73(16) . . ?
C8 C11 H11 114.7 . . ?
C25 C11 H11 114.7 . . ?
C25 C11 C8 120.32(14) . . ?
C10 C11 H11 114.7 . . ?
C10 C11 C8 60.64(11) . . ?
C10 C11 C25 121.20(15) . . ?
N2 C9 C8 111.21(15) . . ?
N2 C9 C24 121.68(16) . . ?
C8 C9 C24 127.02(16) . . ?
C7 C8 C11 114.40(14) . . ?
C7 C8 C10 123.34(14) . . ?
C9 C8 C7 104.73(14) . . ?
C9 C8 C11 125.77(13) . . ?
C9 C8 C10 125.13(15) . . ?
C10 C8 C11 57.70(10) . . ?
O2 C25 C12 122.17(15) . . ?
O2 C25 C11 120.33(16) . . ?
C12 C25 C11 117.49(15) . . ?
C12 C17 H17 119.9 . . ?
C16 C17 C12 120.26(16) . . ?
C16 C17 H17 119.9 . . ?
C6 C1 Cl1 120.55(13) . . ?
C2 C1 Cl1 118.75(14) . . ?
C2 C1 C6 120.61(16) . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.72(16) . . ?
C5 C4 H4 120.1 . . ?
C11 C10 C8 61.66(11) . . ?
C11 C10 H10 114.6 . . ?
C11 C10 C18 120.52(15) . . ?
C8 C10 H10 114.6 . . ?
C18 C10 C8 120.92(14) . . ?
C18 C10 H10 114.6 . . ?
C18 C23 N3 121.12(15) . . ?
C22 C23 N3 116.41(14) . . ?
C22 C23 C18 122.45(16) . . ?
C4 C3 H3 119.7 . . ?
C4 C3 C2 120.63(17) . . ?
C2 C3 H3 119.7 . . ?
C18 C19 H19 119.1 . . ?
C18 C19 C20 121.90(16) . . ?
C20 C19 H19 119.1 . . ?
C23 C18 C10 124.70(15) . . ?
C19 C18 C10 118.74(14) . . ?
C19 C18 C23 116.56(15) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.75(18) . . ?
C14 C13 H13 120.1 . . ?
C23 C22 H22 120.4 . . ?
C21 C22 C23 119.26(16) . . ?
C21 C22 H22 120.4 . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.38(17) . . ?
C4 C5 H5 119.8 . . ?
C9 C24 H24A 109.5 . . ?
C9 C24 H24B 109.5 . . ?
C9 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 C2 C3 119.47(17) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 119.97(18) . . ?
C15 C16 H16 120.0 . . ?
C16 C15 H15 119.9 . . ?
C16 C15 C14 120.16(17) . . ?
C14 C15 H15 119.9 . . ?
C22 C21 H21 120.1 . . ?
C22 C21 C20 119.78(17) . . ?
C20 C21 H21 120.1 . . ?
C19 C20 C21 120.03(17) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.34(17) . . ?
C15 C14 H14 119.8 . . ?

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
Cl1 C1 C2 C3 -174.35(13) . . . . ?
O1 C7 C8 C11 41.8(2) . . . . ?
O1 C7 C8 C9 -176.69(16) . . . . ?
O1 C7 C8 C10 -24.4(3) . . . . ?
O3 N3 C23 C18 -23.8(2) . . . . ?
O3 N3 C23 C22 155.20(16) . . . . ?
O4 N3 C23 C18 156.02(16) . . . . ?
O4 N3 C23 C22 -24.9(2) . . . . ?
N1 N2 C9 C8 -0.36(18) . . . . ?
N1 N2 C9 C24 -177.17(14) . . . . ?
N1 C7 C8 C11 -135.92(14) . . . . ?
N1 C7 C8 C9 5.61(16) . . . . ?
N1 C7 C8 C10 157.90(14) . . . . ?
N1 C6 C1 Cl1 -5.4(2) . . . . ?
N1 C6 C1 C2 178.18(15) . . . . ?
N1 C6 C5 C4 -179.86(15) . . . . ?
N3 C23 C18 C10 -3.0(3) . . . . ?
N3 C23 C18 C19 177.25(16) . . . . ?
N3 C23 C22 C21 -177.40(17) . . . . ?
N2 N1 C7 O1 175.95(15) . . . . ?
N2 N1 C7 C8 -6.29(17) . . . . ?
N2 N1 C6 C1 128.22(16) . . . . ?
N2 N1 C6 C5 -50.6(2) . . . . ?
N2 C9 C8 C7 -3.36(18) . . . . ?
N2 C9 C8 C11 132.36(17) . . . . ?
N2 C9 C8 C10 -155.00(14) . . . . ?
C7 N1 N2 C9 4.45(18) . . . . ?
C7 N1 C6 C1 -55.7(2) . . . . ?
C7 N1 C6 C5 125.46(18) . . . . ?
C7 C8 C10 C11 99.73(17) . . . . ?
C7 C8 C10 C18 -10.7(2) . . . . ?
C6 N1 N2 C9 -178.89(14) . . . . ?
C6 N1 C7 O1 -0.4(3) . . . . ?
C6 N1 C7 C8 177.41(15) . . . . ?
C6 C1 C2 C3 2.1(3) . . . . ?
C12 C17 C16 C15 0.8(3) . . . . ?
C12 C13 C14 C15 1.0(3) . . . . ?
C11 C8 C10 C18 -110.45(18) . . . . ?
C11 C10 C18 C23 -143.79(17) . . . . ?
C11 C10 C18 C19 35.9(2) . . . . ?
C9 C8 C10 C11 -113.63(17) . . . . ?
C9 C8 C10 C18 135.92(16) . . . . ?
C8 C11 C25 O2 104.7(2) . . . . ?
C8 C11 C25 C12 -76.4(2) . . . . ?
C8 C11 C10 C18 111.09(17) . . . . ?
C8 C10 C18 C23 -70.6(2) . . . . ?
C8 C10 C18 C19 109.12(18) . . . . ?
C25 C12 C17 C16 178.83(17) . . . . ?
C25 C12 C13 C14 -179.74(16) . . . . ?
C25 C11 C8 C7 133.63(16) . . . . ?
C25 C11 C8 C9 1.5(3) . . . . ?
C25 C11 C8 C10 -111.07(18) . . . . ?
C25 C11 C10 C8 109.66(17) . . . . ?
C25 C11 C10 C18 -139.26(16) . . . . ?
C17 C12 C25 O2 -172.94(17) . . . . ?
C17 C12 C25 C11 8.2(2) . . . . ?
C17 C12 C13 C14 -0.6(3) . . . . ?
C17 C16 C15 C14 -0.3(3) . . . . ?
C1 C6 C5 C4 1.3(2) . . . . ?
C4 C3 C2 C1 0.4(3) . . . . ?
C10 C11 C8 C7 -115.30(16) . . . . ?
C10 C11 C8 C9 112.56(19) . . . . ?
C10 C11 C25 O2 32.8(2) . . . . ?
C10 C11 C25 C12 -148.33(16) . . . . ?
C23 C22 C21 C20 -0.6(3) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C18 C23 C22 C21 1.6(3) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C13 C12 C25 O2 6.2(3) . . . . ?
C13 C12 C25 C11 -172.65(15) . . . . ?
C13 C12 C17 C16 -0.3(3) . . . . ?
C22 C23 C18 C10 178.00(16) . . . . ?
C22 C23 C18 C19 -1.7(3) . . . . ?
C22 C21 C20 C19 -0.2(3) . . . . ?
C5 C6 C1 Cl1 173.45(13) . . . . ?
C5 C6 C1 C2 -2.9(2) . . . . ?
C5 C4 C3 C2 -2.1(3) . . . . ?
C24 C9 C8 C7 173.24(15) . . . . ?
C24 C9 C8 C11 -51.0(3) . . . . ?
C24 C9 C8 C10 21.6(2) . . . . ?
C16 C15 C14 C13 -0.6(3) . . . . ?
C20 C19 C18 C10 -178.84(17) . . . . ?
C20 C19 C18 C23 0.9(3) . . . . ?

_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 1.232
_oxdiff_exptl_absorpt_empirical_full_min 0.817
####################################################################### 
# 
# 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_mhf
_database_code_depnum_ccdc_archive 'CCDC 1882528'
loop_
_audit_author_name
_audit_author_address
'Huifang Ma'
;xinjiang university
China
;
_audit_update_record             
;
2018-12-01 deposited with the CCDC.	2022-09-28 downloaded from the CCDC.
;
_audit_creation_date             2018-10-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H17 Br2 N O3'
_chemical_formula_sum            'C25 H17 Br2 N O3'
_chemical_formula_weight         539.21
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0127(4)
_cell_length_b                   10.5218(6)
_cell_length_c                   14.9131(8)
_cell_angle_alpha                78.549(5)
_cell_angle_beta                 83.673(5)
_cell_angle_gamma                76.958(5)
_cell_volume                     1048.19(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5486
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.1880
_cell_measurement_theta_min      2.2420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.895
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48416
_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            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11956
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         2.240
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_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    -60.00  40.00   1.00    1.50    --   11.74 -57.00   0.00  100
  2  ω    -21.00  88.00   1.00    1.50    --   11.74  77.00 -90.00  109
  3  ω    -16.00  85.00   1.00    1.50    --   11.74  57.00 150.00  101
  4  ω     34.00  99.00   1.00    1.50    --   11.74-178.00   0.00   65
  5  ω    -16.00  25.00   1.00    1.50    --   11.74  57.00  30.00   41
  6  ω    -20.00  53.00   1.00    1.50    --   11.74 -99.00-180.00   73
;
_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      -0.0820459000
_diffrn_orient_matrix_UB_12      -0.0045901000
_diffrn_orient_matrix_UB_13      0.0319265000
_diffrn_orient_matrix_UB_21      0.0210836000
_diffrn_orient_matrix_UB_22      0.0501874000
_diffrn_orient_matrix_UB_23      0.0204712000
_diffrn_orient_matrix_UB_31      -0.0604483000
_diffrn_orient_matrix_UB_32      0.0490672000
_diffrn_orient_matrix_UB_33      -0.0304581000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3270
_reflns_number_total             3711
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3711
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.039
_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)+(0.0306P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0705
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C25(H25), C15(H15), C6(H6), C24(H24), C21(H21), C5(H5),
 C16(H16), C22(H22), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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
Br2 Br 1.14995(4) -0.00099(3) 0.85589(2) 0.01946(10) Uani 1 1 d . . . . .
Br1 Br -0.11005(4) 1.34990(3) 0.47078(2) 0.02018(10) Uani 1 1 d . . . . .
O1 O 0.6951(3) 0.92359(19) 0.66131(12) 0.0169(4) Uani 1 1 d . . . . .
O3 O 0.5371(3) 0.52025(19) 0.61319(13) 0.0183(5) Uani 1 1 d . . . . .
O2 O 0.2637(3) 0.5630(2) 0.77574(13) 0.0250(5) Uani 1 1 d . . . . .
N1 N 0.3158(3) 0.6318(2) 0.90599(15) 0.0166(5) Uani 1 1 d . . . . .
C1 C 0.3735(4) 1.0124(3) 0.61297(17) 0.0114(6) Uani 1 1 d . . . . .
C2 C 0.4123(4) 1.1375(3) 0.57836(17) 0.0130(6) Uani 1 1 d . . . . .
H2 H 0.536857 1.152082 0.582242 0.016 Uiso 1 1 calc R . . . .
C7 C 0.5343(4) 0.9030(3) 0.65110(17) 0.0135(6) Uani 1 1 d . . . . .
C8 C 0.4945(4) 0.7666(3) 0.67749(17) 0.0119(6) Uani 1 1 d . . . . .
H8 H 0.387669 0.750851 0.646716 0.014 Uiso 1 1 calc R . . . .
C4 C 0.0858(4) 1.2165(3) 0.53293(17) 0.0143(6) Uani 1 1 d . . . . .
C3 C 0.2710(4) 1.2405(3) 0.53847(17) 0.0141(6) Uani 1 1 d . . . . .
H3 H 0.298640 1.323819 0.515854 0.017 Uiso 1 1 calc R . . . .
C20 C 0.7659(4) 0.3979(3) 0.71918(17) 0.0126(6) Uani 1 1 d . . . . .
C25 C 0.9438(4) 0.3958(3) 0.75469(18) 0.0175(6) Uani 1 1 d . . . . .
H25 H 0.986115 0.474492 0.750900 0.021 Uiso 1 1 calc R . . . .
C15 C 0.7034(4) 0.8122(3) 0.86755(18) 0.0152(6) Uani 1 1 d . . . . .
H15 H 0.793758 0.833898 0.819623 0.018 Uiso 1 1 calc R . . . .
C6 C 0.1834(4) 0.9935(3) 0.60929(17) 0.0138(6) Uani 1 1 d . . . . .
H6 H 0.153174 0.911485 0.633991 0.017 Uiso 1 1 calc R . . . .
C14 C 0.5642(4) 0.7430(3) 0.85643(17) 0.0138(6) Uani 1 1 d . . . . .
C10 C 0.6560(4) 0.6495(3) 0.69982(17) 0.0123(6) Uani 1 1 d . . . . .
H10 H 0.787447 0.667939 0.697732 0.015 Uiso 1 1 calc R . . . .
C24 C 1.0561(4) 0.2777(3) 0.79511(19) 0.0190(7) Uani 1 1 d . . . . .
H24 H 1.174392 0.276229 0.818431 0.023 Uiso 1 1 calc R . . . .
C23 C 0.9917(4) 0.1614(3) 0.80081(18) 0.0154(6) Uani 1 1 d . . . . .
C13 C 0.4379(4) 0.7057(3) 0.93125(18) 0.0130(6) Uani 1 1 d . . . . .
C21 C 0.7051(4) 0.2793(3) 0.72629(17) 0.0148(6) Uani 1 1 d . . . . .
H21 H 0.587782 0.279877 0.702451 0.018 Uiso 1 1 calc R . . . .
C5 C 0.0402(4) 1.0955(3) 0.56937(17) 0.0150(6) Uani 1 1 d . . . . .
H5 H -0.085845 1.082435 0.567151 0.018 Uiso 1 1 calc R . . . .
C19 C 0.6456(4) 0.5218(3) 0.67103(17) 0.0128(6) Uani 1 1 d . . . . .
C16 C 0.7049(4) 0.8488(3) 0.95286(18) 0.0183(7) Uani 1 1 d . . . . .
H16 H 0.796328 0.896372 0.961352 0.022 Uiso 1 1 calc R . . . .
C9 C 0.5139(4) 0.6925(3) 0.77780(17) 0.0136(6) Uani 1 1 d . . . . .
C11 C 0.3512(4) 0.6193(3) 0.81613(18) 0.0163(6) Uani 1 1 d . . . . .
C22 C 0.8144(4) 0.1613(3) 0.76771(18) 0.0156(6) Uani 1 1 d . . . . .
H22 H 0.770538 0.082806 0.773501 0.019 Uiso 1 1 calc R . . . .
C17 C 0.5728(4) 0.8153(3) 1.02427(19) 0.0195(7) Uani 1 1 d . . . . .
H17 H 0.573733 0.843173 1.079590 0.023 Uiso 1 1 calc R . . . .
C18 C 0.4383(4) 0.7407(3) 1.01531(18) 0.0193(7) Uani 1 1 d . . . . .
H18 H 0.352048 0.715523 1.064112 0.023 Uiso 1 1 calc R . . . .
C12 C 0.1693(4) 0.5762(3) 0.9664(2) 0.0237(7) Uani 1 1 d . . . . .
H12A H 0.231000 0.513742 1.016270 0.035 Uiso 1 1 calc GR . . . .
H12B H 0.102575 0.532008 0.933158 0.035 Uiso 1 1 calc GR . . . .
H12C H 0.076401 0.645835 0.990042 0.035 Uiso 1 1 calc GR . . . .


_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
Br2 C23 1.901(3) . ?
Br1 C4 1.900(3) . ?
O1 C7 1.225(3) . ?
O3 C19 1.216(3) . ?
O2 C11 1.216(3) . ?
N1 C13 1.403(3) . ?
N1 C11 1.363(3) . ?
N1 C12 1.438(4) . ?
C1 C2 1.391(4) . ?
C1 C7 1.488(4) . ?
C1 C6 1.400(4) . ?
C2 C3 1.378(4) . ?
C7 C8 1.492(4) . ?
C8 C10 1.484(4) . ?
C8 C9 1.548(3) . ?
C4 C3 1.392(4) . ?
C4 C5 1.375(4) . ?
C20 C25 1.402(4) . ?
C20 C21 1.389(4) . ?
C20 C19 1.480(4) . ?
C25 C24 1.376(4) . ?
C15 C14 1.384(4) . ?
C15 C16 1.402(4) . ?
C6 C5 1.380(4) . ?
C14 C13 1.396(4) . ?
C14 C9 1.485(4) . ?
C10 C19 1.508(4) . ?
C10 C9 1.517(4) . ?
C24 C23 1.382(4) . ?
C23 C22 1.387(4) . ?
C13 C18 1.376(4) . ?
C21 C22 1.371(4) . ?
C16 C17 1.378(4) . ?
C9 C11 1.517(4) . ?
C17 C18 1.388(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
C13 N1 C12 124.8(2) . . ?
C11 N1 C13 111.8(2) . . ?
C11 N1 C12 123.4(2) . . ?
C2 C1 C7 119.5(2) . . ?
C2 C1 C6 118.3(2) . . ?
C6 C1 C7 122.2(3) . . ?
C3 C2 C1 121.7(2) . . ?
O1 C7 C1 121.4(3) . . ?
O1 C7 C8 120.5(2) . . ?
C1 C7 C8 118.1(2) . . ?
C7 C8 C9 119.7(2) . . ?
C10 C8 C7 121.0(2) . . ?
C10 C8 C9 59.98(17) . . ?
C3 C4 Br1 120.5(2) . . ?
C5 C4 Br1 117.9(2) . . ?
C5 C4 C3 121.6(2) . . ?
C2 C3 C4 118.3(3) . . ?
C25 C20 C19 122.0(3) . . ?
C21 C20 C25 118.8(3) . . ?
C21 C20 C19 119.2(2) . . ?
C24 C25 C20 120.2(3) . . ?
C14 C15 C16 118.4(3) . . ?
C5 C6 C1 120.7(3) . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 C9 133.7(3) . . ?
C13 C14 C9 107.0(2) . . ?
C8 C10 C19 118.5(2) . . ?
C8 C10 C9 62.12(17) . . ?
C19 C10 C9 117.4(2) . . ?
C25 C24 C23 119.5(3) . . ?
C24 C23 Br2 118.9(2) . . ?
C24 C23 C22 121.3(3) . . ?
C22 C23 Br2 119.8(2) . . ?
C14 C13 N1 109.8(2) . . ?
C18 C13 N1 127.4(3) . . ?
C18 C13 C14 122.8(3) . . ?
C22 C21 C20 121.4(2) . . ?
C4 C5 C6 119.4(2) . . ?
O3 C19 C20 121.4(3) . . ?
O3 C19 C10 121.3(2) . . ?
C20 C19 C10 117.2(2) . . ?
C17 C16 C15 120.9(3) . . ?
C14 C9 C8 127.4(2) . . ?
C14 C9 C10 125.7(2) . . ?
C14 C9 C11 105.0(2) . . ?
C10 C9 C8 57.90(16) . . ?
C10 C9 C11 120.7(2) . . ?
C11 C9 C8 114.7(2) . . ?
O2 C11 N1 125.6(3) . . ?
O2 C11 C9 127.9(2) . . ?
N1 C11 C9 106.4(2) . . ?
C21 C22 C23 118.7(3) . . ?
C16 C17 C18 121.3(3) . . ?
C13 C18 C17 117.2(3) . . ?

_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 1.576
_oxdiff_exptl_absorpt_empirical_full_min 0.784
