# 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_abs
_database_code_depnum_ccdc_archive 'CCDC 2375380'
loop_
_audit_author_name
_audit_author_address
'Alireza Abbasi'
;University of Tehran
Iran
;
_audit_update_record             
;
2024-08-02 deposited with the CCDC.	2024-09-22 downloaded from the CCDC.
;
_audit_creation_date             2024-04-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 F2 N O3'
_chemical_formula_sum            'C14 H9 F2 N O3'
_chemical_formula_weight         277.22
_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                   19.806(8)
_cell_length_b                   4.4215(9)
_cell_length_c                   16.055(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.91(2)
_cell_angle_gamma                90
_cell_volume                     1285.3(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5882
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.995
_cell_measurement_theta_min      2.250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.03288
_exptl_absorpt_correction_T_min  0.97557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, R. H. (1995).Acta Cryst.A51,33+-38'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5882
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.250
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  Marresearch
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1623
_reflns_number_total             2214
_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       'Automar software package (3.3a, 2015)'
_computing_data_collection       'MAR345 dtb Program (1.24-4, 2013)'
_computing_data_reduction        'Automar software package (3.3a, 2015)'
_computing_molecular_graphics    PLATON
_computing_publication_material  DIAMOND
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS 2013/1 (Sheldrick, 2013)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0786
_refine_ls_restrained_S_all      1.168
_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)+(0.0446P)²+1.2663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.1736
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C013(H01A,H01B), C018(H01C,H01D), C019(H01E,H01F)
2.b :
 C015(H015), C016(H016), C022(H022)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
F001 F 0.58125(11) 0.5351(5) 0.14474(15) 0.0679(7) Uani 1 1 d . . . . .
F002 F 0.72404(12) 0.0610(5) 0.00746(15) 0.0704(7) Uani 1 1 d . . . . .
C003 C 0.7074(2) 0.6365(8) 0.1914(2) 0.0496(9) Uani 1 1 d . . . . .
C004 C 0.64565(19) 0.4909(8) 0.1364(2) 0.0502(9) Uani 1 1 d . . . . .
O005 O 0.83826(13) 0.3740(6) 0.11336(18) 0.0622(7) Uani 1 1 d . . . . .
N006 N 0.77162(16) 0.6052(7) 0.1848(2) 0.0528(8) Uani 1 1 d . . . . .
O007 O 0.70111(14) 0.8205(6) 0.25470(18) 0.0659(8) Uani 1 1 d . . . . .
C008 C 0.77437(19) 0.4192(8) 0.1228(2) 0.0508(9) Uani 1 1 d . . . . .
C009 C 0.7144(2) 0.2583(8) 0.0656(2) 0.0501(9) Uani 1 1 d . . . . .
O010 O 0.58320(14) 0.1522(7) 0.02247(17) 0.0652(8) Uani 1 1 d . . . . .
C011 C 0.64732(19) 0.2924(8) 0.0711(2) 0.0483(8) Uani 1 1 d . . . . .
C012 C 0.9596(2) 0.4947(11) 0.1434(3) 0.0719(12) Uani 1 1 d . . . . .
C013 C 0.5721(2) 0.0039(10) -0.0614(3) 0.0642(11) Uani 1 1 d . . . . .
H01A H 0.608495 -0.155363 -0.049538 0.077 Uiso 1 1 calc R U . . .
H01B H 0.523563 -0.089018 -0.086196 0.077 Uiso 1 1 calc R U . . .
C014 C 0.8131(2) 0.7540(10) 0.3849(3) 0.0629(11) Uani 1 1 d . . . . .
C015 C 0.8506(3) 0.5940(12) 0.4417(3) 0.0833(14) Uani 1 1 d . . . . .
H015 H 0.880747 0.465136 0.487418 0.100 Uiso 1 1 calc R U . . .
C016 C 0.5829(2) 0.3726(12) -0.1812(3) 0.0764(12) Uani 1 1 d . . . . .
H016 H 0.586890 0.503736 -0.224226 0.092 Uiso 1 1 calc R U . . .
C017 C 0.5779(2) 0.2086(10) -0.1273(3) 0.0604(10) Uani 1 1 d . . . . .
C018 C 0.7666(2) 0.9633(9) 0.3173(3) 0.0676(11) Uani 1 1 d . . . . .
H01C H 0.753307 1.128981 0.347269 0.081 Uiso 1 1 calc R U . . .
H01D H 0.793822 1.046746 0.284152 0.081 Uiso 1 1 calc R U . . .
C019 C 0.8988(2) 0.5609(10) 0.1686(3) 0.0696(12) Uani 1 1 d . . . . .
H01E H 0.912581 0.517146 0.232612 0.083 Uiso 1 1 calc R U . . .
H01F H 0.885306 0.772775 0.157971 0.083 Uiso 1 1 calc R U . . .
C022 C 1.0084(3) 0.4465(14) 0.1237(4) 0.0999(17) Uani 1 1 d . . . . .
H022 H 1.047801 0.407476 0.107789 0.120 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
F001 C004 1.349(4) . ?
F002 C009 1.347(4) . ?
C003 C004 1.347(5) . ?
C003 N006 1.326(4) . ?
C003 O007 1.346(4) . ?
C004 C011 1.379(5) . ?
O005 C008 1.349(4) . ?
O005 C019 1.430(5) . ?
N006 C008 1.310(4) . ?
O007 C018 1.427(5) . ?
C008 C009 1.370(5) . ?
C009 C011 1.374(5) . ?
O010 C011 1.343(4) . ?
O010 C013 1.433(4) . ?
C012 C019 1.448(6) . ?
C012 C022 1.152(6) . ?
C013 H01A 0.9700 . ?
C013 H01B 0.9700 . ?
C013 C017 1.432(6) . ?
C014 C015 1.155(6) . ?
C014 C018 1.440(6) . ?
C015 H015 0.9300 . ?
C016 H016 0.9300 . ?
C016 C017 1.163(6) . ?
C018 H01C 0.9700 . ?
C018 H01D 0.9700 . ?
C019 H01E 0.9700 . ?
C019 H01F 0.9700 . ?
C022 H022 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
N006 C003 C004 122.9(3) . . ?
N006 C003 O007 120.6(3) . . ?
O007 C003 C004 116.5(3) . . ?
F001 C004 C011 118.9(3) . . ?
C003 C004 F001 120.6(3) . . ?
C003 C004 C011 120.5(3) . . ?
C008 O005 C019 115.7(3) . . ?
C008 N006 C003 117.6(3) . . ?
C003 O007 C018 117.6(3) . . ?
O005 C008 C009 116.5(3) . . ?
N006 C008 O005 120.6(3) . . ?
N006 C008 C009 122.9(3) . . ?
F002 C009 C008 118.2(3) . . ?
F002 C009 C011 121.9(3) . . ?
C008 C009 C011 119.9(3) . . ?
C011 O010 C013 120.4(3) . . ?
C009 C011 C004 116.1(3) . . ?
O010 C011 C004 115.3(3) . . ?
O010 C011 C009 128.5(3) . . ?
C022 C012 C019 179.0(6) . . ?
O010 C013 H01A 109.2 . . ?
O010 C013 H01B 109.2 . . ?
H01A C013 H01B 107.9 . . ?
C017 C013 O010 112.2(3) . . ?
C017 C013 H01A 109.2 . . ?
C017 C013 H01B 109.2 . . ?
C015 C014 C018 177.4(5) . . ?
C014 C015 H015 180.0 . . ?
C017 C016 H016 180.0 . . ?
C016 C017 C013 179.3(5) . . ?
O007 C018 C014 111.6(3) . . ?
O007 C018 H01C 109.3 . . ?
O007 C018 H01D 109.3 . . ?
C014 C018 H01C 109.3 . . ?
C014 C018 H01D 109.3 . . ?
H01C C018 H01D 108.0 . . ?
O005 C019 C012 107.1(3) . . ?
O005 C019 H01E 110.3 . . ?
O005 C019 H01F 110.3 . . ?
C012 C019 H01E 110.3 . . ?
C012 C019 H01F 110.3 . . ?
H01E C019 H01F 108.6 . . ?
C012 C022 H022 180.0 . . ?

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
F001 C004 C011 C009 179.6(3) . . . . ?
F001 C004 C011 O010 -1.8(5) . . . . ?
F002 C009 C011 C004 176.9(3) . . . . ?
F002 C009 C011 O010 -1.4(6) . . . . ?
C003 C004 C011 C009 -0.9(5) . . . . ?
C003 C004 C011 O010 177.7(3) . . . . ?
C003 N006 C008 O005 -179.1(3) . . . . ?
C003 N006 C008 C009 -0.1(5) . . . . ?
C003 O007 C018 C014 -74.8(4) . . . . ?
C004 C003 N006 C008 -1.3(5) . . . . ?
C004 C003 O007 C018 176.4(3) . . . . ?
O005 C008 C009 F002 2.5(5) . . . . ?
O005 C008 C009 C011 -180.0(3) . . . . ?
N006 C003 C004 F001 -178.7(3) . . . . ?
N006 C003 C004 C011 1.8(6) . . . . ?
N006 C003 O007 C018 -3.9(5) . . . . ?
N006 C008 C009 F002 -176.5(3) . . . . ?
N006 C008 C009 C011 1.0(6) . . . . ?
O007 C003 C004 F001 1.0(5) . . . . ?
O007 C003 C004 C011 -178.5(3) . . . . ?
O007 C003 N006 C008 179.0(3) . . . . ?
C008 O005 C019 C012 -175.6(3) . . . . ?
C008 C009 C011 C004 -0.5(5) . . . . ?
C008 C009 C011 O010 -178.8(3) . . . . ?
C011 O010 C013 C017 -60.4(5) . . . . ?
C013 O010 C011 C004 163.8(3) . . . . ?
C013 O010 C011 C009 -17.9(6) . . . . ?
C019 O005 C008 N006 -5.6(5) . . . . ?
C019 O005 C008 C009 175.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_abs_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2375381'
loop_
_audit_author_name
_audit_author_address
'Alireza Abbasi'
;University of Tehran
Iran
;
_audit_update_record             
;
2024-08-02 deposited with the CCDC.	2024-09-22 downloaded from the CCDC.
;
_audit_creation_date             2024-02-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H9 Br Cl4 N4 O'
_chemical_formula_sum            'C15 H9 Br Cl4 N4 O'
_chemical_formula_weight         482.97
_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'
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   13.020(3)
_cell_length_b                   9.949(4)
_cell_length_c                   27.886(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.46(3)
_cell_angle_gamma                90
_cell_volume                     3605.7(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7482
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.999
_cell_measurement_theta_min      1.463
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.885
_exptl_absorpt_correction_T_max  1.42176
_exptl_absorpt_correction_T_min  0.69183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, R. H. (1995).Acta Cryst.A51,33+-38'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7482
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.463
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  Marresearch
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2196
_reflns_number_total             3094
_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       'Automar software package (3.3a, 2015)'
_computing_data_collection       'MAR345 dtb Program (1.24-4, 2013)'
_computing_data_reduction        'Automar software package (3.3a, 2015)'
_computing_molecular_graphics    PLATON
_computing_publication_material  DIAMOND
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS 2013/1 (Sheldrick, 2013)'
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       0.0043(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3094
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1046
_refine_ls_R_factor_gt           0.0771
_refine_ls_restrained_S_all      1.063
_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)+(0.1135P)²+7.6473P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2002
_refine_ls_wR_factor_ref         0.2207
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C019(H01A,H01B), C023(H02A,H02B)
2.b Aromatic/amide H refined with riding coordinates:
 C011(H011), C014(H014), C021(H021), C022(H022), C026(H026)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Br01 Br 0.11036(8) 0.29169(10) 0.18393(3) 0.1118(5) Uani 1 1 d . . . . .
Cl02 Cl -0.37177(14) -0.74385(19) 0.06117(7) 0.0866(6) Uani 1 1 d . . . . .
Cl03 Cl -0.15354(16) -0.4394(2) 0.22788(7) 0.0926(6) Uani 1 1 d . . . . .
Cl04 Cl -0.46287(14) -0.7600(2) 0.16350(8) 0.0951(6) Uani 1 1 d . . . . .
Cl05 Cl -0.35803(15) -0.5921(2) 0.24697(7) 0.0921(6) Uani 1 1 d . . . . .
C006 C -0.2240(5) -0.5933(6) 0.1054(2) 0.0629(14) Uani 1 1 d . . . . .
N007 N -0.1678(4) -0.1654(5) 0.04832(17) 0.0629(12) Uani 1 1 d . . . . .
O008 O -0.1832(3) -0.5933(4) 0.06265(15) 0.0737(12) Uani 1 1 d . . . . .
N009 N -0.1780(4) -0.5261(5) 0.14072(18) 0.0665(13) Uani 1 1 d . . . . .
C010 C -0.1188(4) -0.3696(7) 0.0486(2) 0.0624(14) Uani 1 1 d . . . . .
C011 C -0.1595(5) -0.2752(6) 0.0760(2) 0.0639(14) Uani 1 1 d . . . . .
H011 H -0.177947 -0.284164 0.107548 0.077 Uiso 1 1 calc R U . . .
N012 N -0.1033(4) -0.3163(6) 0.00533(19) 0.0721(14) Uani 1 1 d . . . . .
C013 C 0.0132(6) 0.1908(7) 0.1470(2) 0.0756(17) Uani 1 1 d . . . . .
C014 C -0.0410(5) 0.0912(7) 0.0728(2) 0.0727(16) Uani 1 1 d . . . . .
H014 H -0.029233 0.072232 0.040888 0.087 Uiso 1 1 calc R U . . .
C015 C -0.1293(4) 0.0466(6) 0.0914(2) 0.0637(14) Uani 1 1 d . . . . .
N016 N -0.1335(4) -0.1883(6) 0.00552(18) 0.0720(14) Uani 1 1 d . . . . .
C017 C -0.2185(5) -0.5293(6) 0.1833(2) 0.0666(15) Uani 1 1 d . . . . .
C018 C -0.3553(4) -0.6686(6) 0.1540(2) 0.0676(15) Uani 1 1 d . . . . .
C019 C -0.2066(5) -0.0326(7) 0.0603(2) 0.0741(17) Uani 1 1 d . . . . .
H01A H -0.269286 -0.042776 0.077127 0.089 Uiso 1 1 calc R U . . .
H01B H -0.223479 0.016893 0.030932 0.089 Uiso 1 1 calc R U . . .
C020 C -0.3145(4) -0.6649(6) 0.1095(2) 0.0638(14) Uani 1 1 d . . . . .
C021 C -0.1459(5) 0.0751(7) 0.1383(2) 0.0745(17) Uani 1 1 d . . . . .
H021 H -0.205826 0.045217 0.151399 0.089 Uiso 1 1 calc R U . . .
C022 C -0.0749(6) 0.1478(7) 0.1665(2) 0.0766(18) Uani 1 1 d . . . . .
H022 H -0.086807 0.167137 0.198275 0.092 Uiso 1 1 calc R U . . .
C023 C -0.0909(4) -0.5127(6) 0.0585(2) 0.0714(17) Uani 1 1 d . . . . .
H02A H -0.051809 -0.547503 0.032685 0.086 Uiso 1 1 calc R U . . .
H02B H -0.048052 -0.518449 0.088127 0.086 Uiso 1 1 calc R U . . .
C024 C -0.3062(5) -0.5965(7) 0.1920(2) 0.0685(15) Uani 1 1 d . . . . .
C026 C 0.0310(6) 0.1635(7) 0.1001(2) 0.0794(18) Uani 1 1 d . . . . .
H026 H 0.090790 0.193394 0.086873 0.095 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
Br01 C013 1.874(7) . ?
Cl02 C020 1.692(6) . ?
Cl03 C017 1.712(6) . ?
Cl04 C018 1.703(6) . ?
Cl05 C024 1.711(6) . ?
C006 O008 1.335(7) . ?
C006 N009 1.305(8) . ?
C006 C020 1.388(8) . ?
N007 C011 1.338(8) . ?
N007 N016 1.319(7) . ?
N007 C019 1.461(8) . ?
O008 C023 1.455(7) . ?
N009 C017 1.329(8) . ?
C010 C011 1.340(8) . ?
C010 N012 1.344(8) . ?
C010 C023 1.491(9) . ?
C011 H011 0.9300 . ?
N012 N016 1.333(8) . ?
C013 C022 1.368(10) . ?
C013 C026 1.369(9) . ?
C014 H014 0.9300 . ?
C014 C015 1.364(8) . ?
C014 C026 1.375(9) . ?
C015 C019 1.510(9) . ?
C015 C021 1.369(9) . ?
C017 C024 1.359(9) . ?
C018 C020 1.382(9) . ?
C018 C024 1.402(9) . ?
C019 H01A 0.9700 . ?
C019 H01B 0.9700 . ?
C021 H021 0.9300 . ?
C021 C022 1.380(10) . ?
C022 H022 0.9300 . ?
C023 H02A 0.9700 . ?
C023 H02B 0.9700 . ?
C026 H026 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
O008 C006 C020 117.2(5) . . ?
N009 C006 O008 119.0(5) . . ?
N009 C006 C020 123.8(6) . . ?
C011 N007 C019 128.6(5) . . ?
N016 N007 C011 111.2(5) . . ?
N016 N007 C019 120.3(5) . . ?
C006 O008 C023 116.5(5) . . ?
C006 N009 C017 118.3(5) . . ?
C011 C010 N012 108.7(6) . . ?
C011 C010 C023 131.5(6) . . ?
N012 C010 C023 119.7(5) . . ?
N007 C011 C010 105.3(5) . . ?
N007 C011 H011 127.4 . . ?
C010 C011 H011 127.4 . . ?
N016 N012 C010 108.3(5) . . ?
C022 C013 Br01 120.2(5) . . ?
C022 C013 C026 120.8(7) . . ?
C026 C013 Br01 119.0(5) . . ?
C015 C014 H014 119.3 . . ?
C015 C014 C026 121.4(6) . . ?
C026 C014 H014 119.3 . . ?
C014 C015 C019 120.0(6) . . ?
C014 C015 C021 118.8(6) . . ?
C021 C015 C019 121.2(6) . . ?
N007 N016 N012 106.5(5) . . ?
N009 C017 Cl03 115.6(5) . . ?
N009 C017 C024 123.6(6) . . ?
C024 C017 Cl03 120.8(5) . . ?
C020 C018 Cl04 121.2(5) . . ?
C020 C018 C024 118.9(5) . . ?
C024 C018 Cl04 119.8(5) . . ?
N007 C019 C015 112.0(5) . . ?
N007 C019 H01A 109.2 . . ?
N007 C019 H01B 109.2 . . ?
C015 C019 H01A 109.2 . . ?
C015 C019 H01B 109.2 . . ?
H01A C019 H01B 107.9 . . ?
C006 C020 Cl02 120.6(5) . . ?
C018 C020 Cl02 121.9(5) . . ?
C018 C020 C006 117.5(6) . . ?
C015 C021 H021 119.6 . . ?
C015 C021 C022 120.9(6) . . ?
C022 C021 H021 119.6 . . ?
C013 C022 C021 119.1(6) . . ?
C013 C022 H022 120.4 . . ?
C021 C022 H022 120.4 . . ?
O008 C023 C010 110.3(5) . . ?
O008 C023 H02A 109.6 . . ?
O008 C023 H02B 109.6 . . ?
C010 C023 H02A 109.6 . . ?
C010 C023 H02B 109.6 . . ?
H02A C023 H02B 108.1 . . ?
C017 C024 Cl05 121.9(5) . . ?
C017 C024 C018 117.9(6) . . ?
C018 C024 Cl05 120.2(5) . . ?
C013 C026 C014 119.0(7) . . ?
C013 C026 H026 120.5 . . ?
C014 C026 H026 120.5 . . ?

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
Br01 C013 C022 C021 179.2(5) . . . . ?
Br01 C013 C026 C014 -179.1(5) . . . . ?
Cl03 C017 C024 Cl05 1.5(8) . . . . ?
Cl03 C017 C024 C018 -179.7(5) . . . . ?
Cl04 C018 C020 Cl02 3.2(8) . . . . ?
Cl04 C018 C020 C006 -177.0(5) . . . . ?
Cl04 C018 C024 Cl05 -3.8(8) . . . . ?
Cl04 C018 C024 C017 177.5(5) . . . . ?
C006 O008 C023 C010 -83.5(7) . . . . ?
C006 N009 C017 Cl03 179.8(4) . . . . ?
C006 N009 C017 C024 -1.2(9) . . . . ?
O008 C006 N009 C017 -178.7(5) . . . . ?
O008 C006 C020 Cl02 -2.1(8) . . . . ?
O008 C006 C020 C018 178.1(5) . . . . ?
N009 C006 O008 C023 -2.2(8) . . . . ?
N009 C006 C020 Cl02 177.4(5) . . . . ?
N009 C006 C020 C018 -2.4(9) . . . . ?
N009 C017 C024 Cl05 -177.4(5) . . . . ?
N009 C017 C024 C018 1.3(9) . . . . ?
C010 N012 N016 N007 -0.6(6) . . . . ?
C011 N007 N016 N012 0.6(6) . . . . ?
C011 N007 C019 C015 76.7(8) . . . . ?
C011 C010 N012 N016 0.4(7) . . . . ?
C011 C010 C023 O008 69.4(9) . . . . ?
N012 C010 C011 N007 0.0(7) . . . . ?
N012 C010 C023 O008 -110.6(6) . . . . ?
C014 C015 C019 N007 68.7(8) . . . . ?
C014 C015 C021 C022 0.0(10) . . . . ?
C015 C014 C026 C013 0.1(11) . . . . ?
C015 C021 C022 C013 -0.3(10) . . . . ?
N016 N007 C011 C010 -0.4(7) . . . . ?
N016 N007 C019 C015 -102.2(6) . . . . ?
C019 N007 C011 C010 -179.4(5) . . . . ?
C019 N007 N016 N012 179.7(5) . . . . ?
C019 C015 C021 C022 -179.9(6) . . . . ?
C020 C006 O008 C023 177.3(5) . . . . ?
C020 C006 N009 C017 1.8(9) . . . . ?
C020 C018 C024 Cl05 176.8(5) . . . . ?
C020 C018 C024 C017 -1.9(9) . . . . ?
C021 C015 C019 N007 -111.4(7) . . . . ?
C022 C013 C026 C014 -0.4(11) . . . . ?
C023 C010 C011 N007 -180.0(6) . . . . ?
C023 C010 N012 N016 -179.6(5) . . . . ?
C024 C018 C020 Cl02 -177.4(5) . . . . ?
C024 C018 C020 C006 2.4(9) . . . . ?
C026 C013 C022 C021 0.5(11) . . . . ?
C026 C014 C015 C019 180.0(6) . . . . ?
C026 C014 C015 C021 0.1(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
