# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_032-017_mme28
_database_code_depnum_ccdc_archive 'CCDC 2422190'
loop_
_audit_author_name
_audit_author_address
"Dar'ya Spiridonova"
;St Petersburg University
Russia
;
_audit_update_record             
;
2025-02-07 deposited with the CCDC.	2026-06-15 downloaded from the CCDC.
;
_audit_creation_date             2024-05-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H23 Cl3 N5 O3'
_chemical_formula_sum            'C27 H23 Cl3 N5 O3'
_chemical_formula_weight         571.85
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C27 H23 Cl3 N5 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      hexagonal
_space_group_IT_number           169
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z+1/2'
'y, -x+y, z+5/6'
'x-y, x, z+1/6'

_cell_length_a                   19.0210(3)
_cell_length_b                   19.0210(3)
_cell_length_c                   13.5011(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4230.25(15)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    8218
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.7670
_cell_measurement_theta_min      2.6740
_shelx_estimated_absorpt_T_max   0.909
_shelx_estimated_absorpt_T_min   0.804
_exptl_absorpt_coefficient_mu    3.254
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1770
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17903
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.993
_diffrn_reflns_theta_min         2.682
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  41.00   0.50    8.50    --   47.51 -48.00 -98.00  130
  2  ω   -175.00 -83.00   0.50   38.00    -- -106.00-106.00 174.00  184
  3  ω   -105.00 -43.00   0.50   38.00    -- -106.00 144.00  87.00  124
  4  ω    -17.00  20.00   0.50    8.50    --   47.51 -19.00 120.00   74
  5  ω    -13.00  20.00   0.50    8.50    --   47.51 -19.00 -90.00   66
  6  ω     79.00 104.00   0.50    8.50    --   47.51 125.00 -90.00   50
  7  ω     58.00  99.00   0.50   38.00    --  113.25 -77.00 -60.00   82
  8  ω     92.00 133.00   0.50   38.00    --  113.25  77.00 150.00   82
  9  ω     42.00  67.00   0.50   38.00    --  113.25 -61.00 -90.00   50
 10  ω    150.00 177.00   0.50   38.00    --  113.25  45.00  90.00   54
 11  ω    104.00 138.00   0.50   38.00    --  113.25  45.00  90.00   68
 12  ω     42.00  68.00   0.50   38.00    --  113.25 -61.00 120.00   52
 13  ω     42.00 102.00   0.50   38.00    --  113.25 -77.00  30.00  120
 14  ω     98.00 173.00   0.50   38.00    --  113.25  61.00-180.00  150
 15  ω     44.00  71.00   0.50   38.00    --  113.25 -61.00  30.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0648387000
_diffrn_orient_matrix_UB_12      0.0066886000
_diffrn_orient_matrix_UB_13      -0.0612455000
_diffrn_orient_matrix_UB_21      -0.0630409000
_diffrn_orient_matrix_UB_22      -0.0878289000
_diffrn_orient_matrix_UB_23      0.0282378000
_diffrn_orient_matrix_UB_31      -0.0236192000
_diffrn_orient_matrix_UB_32      0.0313838000
_diffrn_orient_matrix_UB_33      0.0920637000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_full    0.867
_reflns_Friedel_fraction_max     0.866
_reflns_number_gt                4606
_reflns_number_total             5021
_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 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_refine_diff_density_max         0.987
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 
;
 Flack x determined using 1763 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.030(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5021
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0599
_refine_ls_restrained_S_all      1.041
_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)+(0.1063P)²+2.1454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1636
_refine_ls_wR_factor_ref         0.1675
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(Cl1)=Sof(H013)=1-FVAR(1)
 Sof(Cl00)=Sof(H00X)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C00E(H00E)
3.b Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00B), C00K(H00C,H00D)
3.c Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00P(H00P), C00Q(H00Q), C00T(H00T), C00V(H00V), C00W(H00W),
 C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012),
 C013(H013)
3.d Idealised Me refined as rotating group:
 C00M(H00F,H00G,H00H), C00N(H00I,H00J,H00K)
;
_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
Cl01 Cl 0.77289(13) 0.05645(12) 0.06711(15) 0.0714(5) Uani 1 1 d . . . . .
Cl02 Cl 0.53493(18) -0.07757(10) 0.22103(14) 0.0886(8) Uani 1 1 d . . . . .
O003 O 0.6445(2) 0.05812(19) 0.5642(3) 0.0357(7) Uani 1 1 d . . . . .
O004 O 0.60114(19) 0.24346(19) 0.4010(3) 0.0347(7) Uani 1 1 d . . . . .
O005 O 0.7745(2) 0.1774(2) 0.3908(3) 0.0439(9) Uani 1 1 d . . . . .
N006 N 0.7107(2) 0.2881(2) 0.5019(3) 0.0271(7) Uani 1 1 d . . . . .
N007 N 0.6242(2) 0.1493(2) 0.4777(3) 0.0296(8) Uani 1 1 d . . . . .
N008 N 0.7352(2) 0.1915(2) 0.5830(3) 0.0322(8) Uani 1 1 d . . . . .
N009 N 0.8400(2) 0.2977(2) 0.4758(3) 0.0336(8) Uani 1 1 d . . . . .
N00A N 0.9015(3) 0.2731(3) 0.3429(4) 0.0416(11) Uani 1 1 d . . . . .
Cl00 Cl 0.9407(3) 0.1032(4) 0.6774(4) 0.126(2) Uani 0.612(8) 1 d . . P A 1
C00C C 0.6437(3) 0.2297(3) 0.4561(3) 0.0298(9) Uani 1 1 d . . . . .
C00D C 0.6681(3) 0.1286(3) 0.5424(4) 0.0307(9) Uani 1 1 d . . . . .
C00E C 0.7718(3) 0.2734(3) 0.5448(3) 0.0298(9) Uani 1 1 d . . . . .
H00E H 0.794164 0.310381 0.603275 0.036 Uiso 1 1 calc R U . . .
C00F C 0.5593(3) 0.0854(3) 0.4220(4) 0.0350(10) Uani 1 1 d . . . . .
C00G C 0.8180(3) 0.4092(3) 0.4146(4) 0.0339(10) Uani 1 1 d . . . . .
C00H C 0.8342(3) 0.2450(3) 0.4008(4) 0.0356(10) Uani 1 1 d . . . . .
C00I C 0.7421(3) 0.3742(3) 0.4807(4) 0.0314(10) Uani 1 1 d . . . . .
H00A H 0.755796 0.404787 0.543771 0.038 Uiso 1 1 calc R U . . .
H00B H 0.699502 0.380834 0.447247 0.038 Uiso 1 1 calc R U . . .
C00J C 0.7799(3) 0.1760(3) 0.6580(4) 0.0413(12) Uani 1 1 d . . . . .
C00K C 0.8782(3) 0.3865(3) 0.4583(4) 0.0357(10) Uani 1 1 d . . . . .
H00C H 0.924603 0.404086 0.412352 0.043 Uiso 1 1 calc R U . . .
H00D H 0.899468 0.415663 0.521742 0.043 Uiso 1 1 calc R U . . .
C00L C 0.5781(4) 0.0405(3) 0.3568(4) 0.0434(12) Uani 1 1 d . . . . .
H00L H 0.632157 0.050659 0.350694 0.052 Uiso 1 1 calc R U . . .
C00M C 0.8580(3) 0.5020(3) 0.4167(5) 0.0419(12) Uani 1 1 d . . . . .
H00F H 0.820242 0.518122 0.389780 0.063 Uiso 1 1 calc R U . . .
H00G H 0.907518 0.526029 0.376486 0.063 Uiso 1 1 calc R U . . .
H00H H 0.871740 0.521288 0.485121 0.063 Uiso 1 1 calc R U . . .
C00N C 0.7952(3) 0.3780(3) 0.3094(4) 0.0397(11) Uani 1 1 d . . . . .
H00I H 0.762914 0.318593 0.310167 0.060 Uiso 1 1 calc R U . . .
H00J H 0.844602 0.395188 0.270422 0.060 Uiso 1 1 calc R U . . .
H00K H 0.763277 0.400079 0.279685 0.060 Uiso 1 1 calc R U . . .
C00O C 0.9090(3) 0.2275(3) 0.2638(4) 0.0407(12) Uani 1 1 d . . . . .
C00P C 0.7758(4) 0.1952(3) 0.7537(5) 0.0498(14) Uani 1 1 d . . . . .
H00P H 0.743805 0.218893 0.770851 0.060 Uiso 1 1 calc R U . . .
C00Q C 0.8431(4) 0.1721(4) 0.2078(5) 0.0470(13) Uani 1 1 d . . . . .
H00Q H 0.790123 0.163260 0.220351 0.056 Uiso 1 1 calc R U . . .
C00R C 0.8564(4) 0.1298(4) 0.1331(5) 0.0529(14) Uani 1 1 d . . . . .
Cl1 Cl 0.8376(4) 0.2285(5) 0.9320(4) 0.099(3) Uani 0.388(8) 1 d . . P A 2
C00T C 0.4807(3) 0.0714(4) 0.4318(5) 0.0467(14) Uani 1 1 d . . . . .
H00T H 0.468854 0.101752 0.477913 0.056 Uiso 1 1 calc R U . . .
C00U C 0.5151(5) -0.0200(3) 0.3005(5) 0.0602(19) Uani 1 1 d . . . . .
C00V C 0.4189(4) 0.0116(4) 0.3727(5) 0.0596(19) Uani 1 1 d . . . . .
H00V H 0.365235 0.002755 0.377002 0.072 Uiso 1 1 calc R U . . .
C00W C 0.4362(5) -0.0343(4) 0.3082(5) 0.065(2) Uani 1 1 d . . . . .
H00W H 0.394196 -0.075567 0.269354 0.078 Uiso 1 1 calc R U . . .
C00X C 0.8183(5) 0.1805(5) 0.8267(6) 0.072(2) Uani 1 1 d . . . . .
H00X H 0.815667 0.195090 0.893352 0.086 Uiso 0.612(8) 1 calc R U P A 1
C00Y C 0.9861(4) 0.2413(4) 0.2424(7) 0.064(2) Uani 1 1 d . . . . .
H00Y H 1.031709 0.280430 0.278799 0.077 Uiso 1 1 calc R U . . .
C00Z C 0.9313(5) 0.1404(4) 0.1131(6) 0.067(2) Uani 1 1 d . . . . .
H00Z H 0.938449 0.109162 0.063351 0.081 Uiso 1 1 calc R U . . .
C010 C 0.8629(5) 0.1459(5) 0.8045(7) 0.075(2) Uani 1 1 d . . . . .
H010 H 0.888737 0.132194 0.855077 0.090 Uiso 1 1 calc R U . . .
C011 C 0.8288(6) 0.1440(7) 0.6303(7) 0.082(3) Uani 1 1 d . . . . .
H011 H 0.833728 0.131835 0.563337 0.098 Uiso 1 1 calc R U . . .
C012 C 0.9960(5) 0.1971(5) 0.1665(8) 0.077(2) Uani 1 1 d . . . . .
H012 H 1.048932 0.206634 0.151725 0.093 Uiso 1 1 calc R U . . .
C013 C 0.8702(7) 0.1309(8) 0.7073(10) 0.100(4) Uani 1 1 d . . . . .
H013 H 0.905230 0.110468 0.690952 0.120 Uiso 0.388(8) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl01 C00R 1.746(7) . ?
Cl02 C00U 1.705(8) . ?
O003 C00D 1.218(6) . ?
O004 C00C 1.221(6) . ?
O005 C00H 1.225(6) . ?
N006 C00C 1.351(6) . ?
N006 C00E 1.445(6) . ?
N006 C00I 1.462(6) . ?
N007 C00C 1.411(6) . ?
N007 C00D 1.395(6) . ?
N007 C00F 1.438(6) . ?
N008 C00D 1.354(6) . ?
N008 C00E 1.448(6) . ?
N008 C00J 1.444(6) . ?
N009 C00E 1.471(6) . ?
N009 C00H 1.390(7) . ?
N009 C00K 1.486(6) . ?
N00A C00H 1.361(7) . ?
N00A C00O 1.427(7) . ?
Cl00 C013 1.717(10) . ?
C00E H00E 1.0000 . ?
C00F C00L 1.391(8) . ?
C00F C00T 1.388(8) . ?
C00G C00I 1.537(6) . ?
C00G C00K 1.530(7) . ?
C00G C00M 1.534(7) . ?
C00G C00N 1.516(7) . ?
C00I H00A 0.9900 . ?
C00I H00B 0.9900 . ?
C00J C00P 1.355(9) . ?
C00J C011 1.393(10) . ?
C00K H00C 0.9900 . ?
C00K H00D 0.9900 . ?
C00L H00L 0.9500 . ?
C00L C00U 1.400(8) . ?
C00M H00F 0.9800 . ?
C00M H00G 0.9800 . ?
C00M H00H 0.9800 . ?
C00N H00I 0.9800 . ?
C00N H00J 0.9800 . ?
C00N H00K 0.9800 . ?
C00O C00Q 1.390(9) . ?
C00O C00Y 1.385(8) . ?
C00P H00P 0.9500 . ?
C00P C00X 1.389(9) . ?
C00Q H00Q 0.9500 . ?
C00Q C00R 1.390(8) . ?
C00R C00Z 1.363(10) . ?
Cl1 C00X 1.630(11) . ?
C00T H00T 0.9500 . ?
C00T C00V 1.405(9) . ?
C00U C00W 1.388(12) . ?
C00V H00V 0.9500 . ?
C00V C00W 1.385(12) . ?
C00W H00W 0.9500 . ?
C00X H00X 0.9500 . ?
C00X C010 1.343(14) . ?
C00Y H00Y 0.9500 . ?
C00Y C012 1.396(10) . ?
C00Z H00Z 0.9500 . ?
C00Z C012 1.368(12) . ?
C010 H010 0.9500 . ?
C010 C013 1.365(16) . ?
C011 H011 0.9500 . ?
C011 C013 1.399(12) . ?
C012 H012 0.9500 . ?
C013 H013 0.9500 . ?

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
C00C N006 C00E 122.9(4) . . ?
C00C N006 C00I 121.4(4) . . ?
C00E N006 C00I 112.1(4) . . ?
C00C N007 C00F 117.3(4) . . ?
C00D N007 C00C 124.4(4) . . ?
C00D N007 C00F 118.0(4) . . ?
C00D N008 C00E 122.7(4) . . ?
C00D N008 C00J 119.6(4) . . ?
C00J N008 C00E 117.1(4) . . ?
C00E N009 C00K 108.1(4) . . ?
C00H N009 C00E 119.6(4) . . ?
C00H N009 C00K 121.5(4) . . ?
C00H N00A C00O 123.5(4) . . ?
O004 C00C N006 123.8(4) . . ?
O004 C00C N007 120.9(4) . . ?
N006 C00C N007 115.2(4) . . ?
O003 C00D N007 121.3(4) . . ?
O003 C00D N008 122.7(5) . . ?
N008 C00D N007 115.9(4) . . ?
N006 C00E N008 110.6(4) . . ?
N006 C00E N009 110.7(4) . . ?
N006 C00E H00E 106.3 . . ?
N008 C00E N009 115.9(4) . . ?
N008 C00E H00E 106.3 . . ?
N009 C00E H00E 106.3 . . ?
C00L C00F N007 118.4(5) . . ?
C00T C00F N007 119.9(5) . . ?
C00T C00F C00L 121.7(5) . . ?
C00K C00G C00I 109.1(4) . . ?
C00K C00G C00M 107.9(4) . . ?
C00M C00G C00I 107.8(4) . . ?
C00N C00G C00I 110.6(4) . . ?
C00N C00G C00K 111.1(4) . . ?
C00N C00G C00M 110.4(4) . . ?
O005 C00H N009 122.4(5) . . ?
O005 C00H N00A 123.0(5) . . ?
N00A C00H N009 114.5(4) . . ?
N006 C00I C00G 111.6(4) . . ?
N006 C00I H00A 109.3 . . ?
N006 C00I H00B 109.3 . . ?
C00G C00I H00A 109.3 . . ?
C00G C00I H00B 109.3 . . ?
H00A C00I H00B 108.0 . . ?
C00P C00J N008 119.6(5) . . ?
C00P C00J C011 120.9(6) . . ?
C011 C00J N008 119.4(6) . . ?
N009 C00K C00G 111.8(4) . . ?
N009 C00K H00C 109.2 . . ?
N009 C00K H00D 109.2 . . ?
C00G C00K H00C 109.2 . . ?
C00G C00K H00D 109.2 . . ?
H00C C00K H00D 107.9 . . ?
C00F C00L H00L 121.0 . . ?
C00F C00L C00U 118.1(6) . . ?
C00U C00L H00L 121.0 . . ?
C00G C00M H00F 109.5 . . ?
C00G C00M H00G 109.5 . . ?
C00G C00M H00H 109.5 . . ?
H00F C00M H00G 109.5 . . ?
H00F C00M H00H 109.5 . . ?
H00G C00M H00H 109.5 . . ?
C00G C00N H00I 109.5 . . ?
C00G C00N H00J 109.5 . . ?
C00G C00N H00K 109.5 . . ?
H00I C00N H00J 109.5 . . ?
H00I C00N H00K 109.5 . . ?
H00J C00N H00K 109.5 . . ?
C00Q C00O N00A 122.8(5) . . ?
C00Y C00O N00A 117.3(5) . . ?
C00Y C00O C00Q 119.9(5) . . ?
C00J C00P H00P 119.8 . . ?
C00J C00P C00X 120.4(7) . . ?
C00X C00P H00P 119.8 . . ?
C00O C00Q H00Q 120.8 . . ?
C00R C00Q C00O 118.5(6) . . ?
C00R C00Q H00Q 120.8 . . ?
C00Q C00R Cl01 118.4(5) . . ?
C00Z C00R Cl01 118.9(5) . . ?
C00Z C00R C00Q 122.6(7) . . ?
C00F C00T H00T 120.5 . . ?
C00F C00T C00V 119.1(7) . . ?
C00V C00T H00T 120.5 . . ?
C00L C00U Cl02 119.8(7) . . ?
C00W C00U Cl02 119.0(5) . . ?
C00W C00U C00L 121.2(7) . . ?
C00T C00V H00V 120.0 . . ?
C00W C00V C00T 120.1(7) . . ?
C00W C00V H00V 120.0 . . ?
C00U C00W H00W 120.1 . . ?
C00V C00W C00U 119.8(5) . . ?
C00V C00W H00W 120.1 . . ?
C00P C00X Cl1 119.8(7) . . ?
C00P C00X H00X 119.5 . . ?
C010 C00X C00P 120.9(8) . . ?
C010 C00X Cl1 116.7(7) . . ?
C010 C00X H00X 119.5 . . ?
C00O C00Y H00Y 120.4 . . ?
C00O C00Y C012 119.2(7) . . ?
C012 C00Y H00Y 120.4 . . ?
C00R C00Z H00Z 120.9 . . ?
C00R C00Z C012 118.3(6) . . ?
C012 C00Z H00Z 120.9 . . ?
C00X C010 H010 120.9 . . ?
C00X C010 C013 118.2(7) . . ?
C013 C010 H010 120.9 . . ?
C00J C011 H011 122.0 . . ?
C00J C011 C013 115.9(9) . . ?
C013 C011 H011 122.0 . . ?
C00Y C012 H012 119.3 . . ?
C00Z C012 C00Y 121.5(7) . . ?
C00Z C012 H012 119.3 . . ?
C010 C013 Cl00 117.8(7) . . ?
C010 C013 C011 123.5(9) . . ?
C010 C013 H013 118.2 . . ?
C011 C013 Cl00 118.5(10) . . ?
C011 C013 H013 118.2 . . ?

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
Cl01 C00R C00Z C012 -178.9(7) . . . . ?
Cl02 C00U C00W C00V 179.7(5) . . . . ?
N007 C00F C00L C00U -178.0(4) . . . . ?
N007 C00F C00T C00V 176.5(5) . . . . ?
N008 C00J C00P C00X 179.8(6) . . . . ?
N008 C00J C011 C013 179.9(8) . . . . ?
N00A C00O C00Q C00R -179.2(6) . . . . ?
N00A C00O C00Y C012 179.0(8) . . . . ?
C00C N006 C00E N008 -32.7(6) . . . . ?
C00C N006 C00E N009 97.2(5) . . . . ?
C00C N006 C00I C00G -104.2(5) . . . . ?
C00C N007 C00D O003 174.0(4) . . . . ?
C00C N007 C00D N008 -2.4(7) . . . . ?
C00C N007 C00F C00L 113.1(5) . . . . ?
C00C N007 C00F C00T -65.0(6) . . . . ?
C00D N007 C00C O004 -177.7(4) . . . . ?
C00D N007 C00C N006 1.1(6) . . . . ?
C00D N007 C00F C00L -61.1(6) . . . . ?
C00D N007 C00F C00T 120.8(5) . . . . ?
C00D N008 C00E N006 31.1(6) . . . . ?
C00D N008 C00E N009 -96.0(5) . . . . ?
C00D N008 C00J C00P -107.2(6) . . . . ?
C00D N008 C00J C011 74.9(8) . . . . ?
C00E N006 C00C O004 -163.1(4) . . . . ?
C00E N006 C00C N007 18.2(6) . . . . ?
C00E N006 C00I C00G 55.0(5) . . . . ?
C00E N008 C00D O003 168.4(4) . . . . ?
C00E N008 C00D N007 -15.3(6) . . . . ?
C00E N008 C00J C00P 81.5(6) . . . . ?
C00E N008 C00J C011 -96.3(7) . . . . ?
C00E N009 C00H O005 -1.5(8) . . . . ?
C00E N009 C00H N00A -178.6(4) . . . . ?
C00E N009 C00K C00G -59.4(5) . . . . ?
C00F N007 C00C O004 8.4(6) . . . . ?
C00F N007 C00C N006 -172.7(4) . . . . ?
C00F N007 C00D O003 -12.2(7) . . . . ?
C00F N007 C00D N008 171.4(4) . . . . ?
C00F C00L C00U Cl02 -179.0(4) . . . . ?
C00F C00L C00U C00W 0.9(8) . . . . ?
C00F C00T C00V C00W 2.2(8) . . . . ?
C00H N009 C00E N006 -82.3(5) . . . . ?
C00H N009 C00E N008 44.6(6) . . . . ?
C00H N009 C00K C00G 84.8(5) . . . . ?
C00H N00A C00O C00Q 31.3(9) . . . . ?
C00H N00A C00O C00Y -149.8(6) . . . . ?
C00I N006 C00C O004 -6.1(7) . . . . ?
C00I N006 C00C N007 175.1(4) . . . . ?
C00I N006 C00E N008 168.4(4) . . . . ?
C00I N006 C00E N009 -61.7(5) . . . . ?
C00I C00G C00K N009 53.2(5) . . . . ?
C00J N008 C00D O003 -2.4(7) . . . . ?
C00J N008 C00D N007 174.0(4) . . . . ?
C00J N008 C00E N006 -158.0(4) . . . . ?
C00J N008 C00E N009 75.0(6) . . . . ?
C00J C00P C00X Cl1 160.2(6) . . . . ?
C00J C00P C00X C010 -1.1(11) . . . . ?
C00J C011 C013 Cl00 -172.3(8) . . . . ?
C00J C011 C013 C010 1.6(18) . . . . ?
C00K N009 C00E N006 62.6(5) . . . . ?
C00K N009 C00E N008 -170.5(4) . . . . ?
C00K N009 C00H O005 -141.7(5) . . . . ?
C00K N009 C00H N00A 41.2(7) . . . . ?
C00K C00G C00I N006 -49.8(5) . . . . ?
C00L C00F C00T C00V -1.5(8) . . . . ?
C00L C00U C00W C00V -0.1(9) . . . . ?
C00M C00G C00I N006 -166.7(4) . . . . ?
C00M C00G C00K N009 170.0(4) . . . . ?
C00N C00G C00I N006 72.6(5) . . . . ?
C00N C00G C00K N009 -68.9(5) . . . . ?
C00O N00A C00H O005 1.1(9) . . . . ?
C00O N00A C00H N009 178.1(5) . . . . ?
C00O C00Q C00R Cl01 176.7(5) . . . . ?
C00O C00Q C00R C00Z 0.3(10) . . . . ?
C00O C00Y C012 C00Z -0.1(14) . . . . ?
C00P C00J C011 C013 2.1(13) . . . . ?
C00P C00X C010 C013 4.6(14) . . . . ?
C00Q C00O C00Y C012 -2.1(11) . . . . ?
C00Q C00R C00Z C012 -2.5(12) . . . . ?
C00R C00Z C012 C00Y 2.4(14) . . . . ?
Cl1 C00X C010 C013 -157.2(9) . . . . ?
C00T C00F C00L C00U 0.0(7) . . . . ?
C00T C00V C00W C00U -1.4(9) . . . . ?
C00X C010 C013 Cl00 169.0(8) . . . . ?
C00X C010 C013 C011 -5.0(18) . . . . ?
C00Y C00O C00Q C00R 2.0(9) . . . . ?
C011 C00J C00P C00X -2.4(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.910
_oxdiff_exptl_absorpt_empirical_full_min 0.507
# start Validation Reply Form
_vrf_PLAT601_032-017_mme28       
;
PROBLEM: Unit Cell Contains Solvent Accessible VOIDS   <=        162 Ang**3
RESPONSE: There are no electron density peaks that describe solvent molecules
;
# end Validation Reply Form
####################################################################### 
# 
# 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_13401_mme7
_database_code_depnum_ccdc_archive 'CCDC 2422716'
loop_
_audit_author_name
_audit_author_address
"Dar'ya Spiridonova"
;St Petersburg University
Russia
;
_audit_update_record             
;
2025-02-10 deposited with the CCDC.	2026-06-15 downloaded from the CCDC.
;
_audit_creation_date             2025-02-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 Br2 N4 S3'
_chemical_formula_sum            'C18 H16 Br2 N4 S3'
_chemical_formula_weight         544.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H16 Br2 N4 S3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.82120(10)
_cell_length_b                   15.4764(4)
_cell_length_c                   22.0939(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.022(2)
_cell_angle_gamma                90
_cell_volume                     1990.15(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6445
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.6850
_cell_measurement_theta_min      3.9460
_shelx_estimated_absorpt_T_max   0.494
_shelx_estimated_absorpt_T_min   0.265
_exptl_absorpt_coefficient_mu    8.207
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.817
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8113
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.994
_diffrn_reflns_theta_min         4.919
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  34.00   1.00    2.00    --  -40.25  38.00 -90.00   31
  2  ω    -65.00 -21.00   1.00    2.00    --  -40.25  38.00 -90.00   44
  3  ω   -113.00 -15.00   1.00    2.00    --  -40.25 -38.00  90.00   98
  4  ω   -130.00-101.00   1.00    2.00    --  -40.25-178.00  90.00   29
  5  ω     35.00  71.00   1.00    2.00    --  113.00-112.00  90.00   36
  6  ω     75.00 112.00   1.00    2.00    --  113.00-112.00  90.00   37
  7  ω     78.00 114.00   1.00    2.00    --  113.00-112.00 -30.00   36
  8  ω     47.00  73.00   1.00    2.00    --  113.00-112.00 -30.00   26
  9  ω     35.00 144.00   1.00    2.00    --  113.00 -30.00  90.00  109
 10  ω     47.00 133.00   1.00    2.00    --  113.00 -77.00  90.00   86
 11  ω     88.00 126.00   1.00    2.00    --   40.25-178.00-150.00   38
 12  ω    100.00 178.00   1.00    2.00    --  113.00  45.00-180.00   78
 13  ω    134.00 159.00   1.00    2.00    --  113.00 112.00 -90.00   25
 14  ω    102.00 138.00   1.00    2.00    --  113.00 112.00-150.00   36
 15  ω     62.00 136.00   1.00    2.00    --  113.00 178.00   0.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0348377000
_diffrn_orient_matrix_UB_12      0.0936654000
_diffrn_orient_matrix_UB_13      0.0218280000
_diffrn_orient_matrix_UB_21      0.0112266000
_diffrn_orient_matrix_UB_22      -0.0316884000
_diffrn_orient_matrix_UB_23      0.0660812000
_diffrn_orient_matrix_UB_31      0.2622516000
_diffrn_orient_matrix_UB_32      -0.0111011000
_diffrn_orient_matrix_UB_33      -0.0045098000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3679
_reflns_number_total             3755
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_refine_diff_density_max         0.866
_refine_diff_density_min         -0.756
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       0.00088(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3755
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.117
_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)+(0.0567P)²+1.8021P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0896
_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:
 C2(H2A,H2B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C17(H17), C18(H18), C22(H22), C23(H23), C25(H25), C26(H26)
;
_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
N1 N 0.9255(4) 0.64132(15) 0.35766(10) 0.0152(5) Uani 1 1 d . . . . .
C2 C 1.1076(4) 0.67146(17) 0.39838(12) 0.0137(5) Uani 1 1 d . . . . .
H2A H 1.111167 0.635424 0.435408 0.016 Uiso 1 1 calc R U . . .
H2B H 1.257745 0.665630 0.378436 0.016 Uiso 1 1 calc R U . . .
N3 N 1.0703(4) 0.76122(15) 0.41470(10) 0.0131(4) Uani 1 1 d . . . . .
C4 C 0.9305(4) 0.78394(17) 0.46200(12) 0.0129(5) Uani 1 1 d . . . . .
S5 S 0.91560(11) 0.70434(4) 0.52278(3) 0.01482(16) Uani 1 1 d . . . . .
S6 S 0.65972(11) 0.62396(4) 0.49131(3) 0.01674(16) Uani 1 1 d . . . . .
S7 S 0.79553(13) 0.52498(4) 0.44181(3) 0.01697(16) Uani 1 1 d . . . . .
C8 C 0.7908(4) 0.57081(16) 0.36579(11) 0.0114(5) Uani 1 1 d . . . . .
C9 C 0.9095(5) 0.69156(18) 0.30123(12) 0.0184(6) Uani 1 1 d . . . . .
H9A H 0.777306 0.671101 0.276338 0.022 Uiso 1 1 calc R U . . .
H9B H 1.050974 0.683516 0.277660 0.022 Uiso 1 1 calc R U . . .
C10 C 0.8789(5) 0.78681(17) 0.31635(12) 0.0160(5) Uani 1 1 d . . . . .
H10A H 0.725852 0.795796 0.334119 0.019 Uiso 1 1 calc R U . . .
H10B H 0.886252 0.821404 0.278739 0.019 Uiso 1 1 calc R U . . .
C11 C 1.0643(5) 0.81755(17) 0.36086(12) 0.0158(5) Uani 1 1 d . . . . .
H11A H 1.215695 0.816447 0.341146 0.019 Uiso 1 1 calc R U . . .
H11B H 1.032142 0.877777 0.373201 0.019 Uiso 1 1 calc R U . . .
N12 N 0.8405(4) 0.85828(15) 0.46503(10) 0.0148(4) Uani 1 1 d . . . . .
C13 C 0.7018(4) 0.88407(17) 0.51373(11) 0.0127(5) Uani 1 1 d . . . . .
C14 C 0.7780(5) 0.94948(18) 0.55262(13) 0.0161(5) Uani 1 1 d . . . . .
H14 H 0.922560 0.976238 0.546398 0.019 Uiso 1 1 calc R U . . .
C15 C 0.6424(5) 0.97549(17) 0.60046(13) 0.0173(6) Uani 1 1 d . . . . .
H15 H 0.695417 1.019047 0.627595 0.021 Uiso 1 1 calc R U . . .
C16 C 0.4316(4) 0.93786(16) 0.60825(11) 0.0119(5) Uani 1 1 d . . . . .
C17 C 0.3468(4) 0.87551(17) 0.56891(12) 0.0138(5) Uani 1 1 d . . . . .
H17 H 0.198429 0.851449 0.574236 0.017 Uiso 1 1 calc R U . . .
C18 C 0.4832(5) 0.84885(18) 0.52148(12) 0.0159(5) Uani 1 1 d . . . . .
H18 H 0.427299 0.806225 0.494002 0.019 Uiso 1 1 calc R U . . .
Br19 Br 0.25910(5) 0.97038(2) 0.67709(2) 0.01585(12) Uani 1 1 d . . . . .
N20 N 0.6681(4) 0.54108(14) 0.32195(10) 0.0126(4) Uani 1 1 d . . . . .
C21 C 0.5293(4) 0.46738(16) 0.32473(11) 0.0115(5) Uani 1 1 d . . . . .
C22 C 0.3153(5) 0.47072(17) 0.29500(12) 0.0146(5) Uani 1 1 d . . . . .
H22 H 0.265443 0.523241 0.276810 0.018 Uiso 1 1 calc R U . . .
C23 C 0.1747(4) 0.39826(18) 0.29172(12) 0.0146(5) Uani 1 1 d . . . . .
H23 H 0.028614 0.401067 0.271945 0.017 Uiso 1 1 calc R U . . .
C24 C 0.2512(4) 0.32185(17) 0.31779(11) 0.0114(5) Uani 1 1 d . . . . .
C25 C 0.4637(4) 0.31602(17) 0.34648(11) 0.0124(5) Uani 1 1 d . . . . .
H25 H 0.513475 0.262961 0.363899 0.015 Uiso 1 1 calc R U . . .
C26 C 0.6033(4) 0.38860(17) 0.34951(11) 0.0120(5) Uani 1 1 d . . . . .
H26 H 0.750586 0.384857 0.368567 0.014 Uiso 1 1 calc R U . . .
Br27 Br 0.06653(4) 0.22053(2) 0.31254(2) 0.01609(12) 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
N1 C2 1.455(3) . ?
N1 C8 1.358(3) . ?
N1 C9 1.471(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 N3 1.452(3) . ?
N3 C4 1.382(3) . ?
N3 C11 1.475(3) . ?
C4 S5 1.826(3) . ?
C4 N12 1.266(4) . ?
S5 S6 2.0524(9) . ?
S6 S7 2.0490(10) . ?
S7 C8 1.823(3) . ?
C8 N20 1.279(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.523(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.523(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N12 C13 1.414(3) . ?
C13 C14 1.395(4) . ?
C13 C18 1.398(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.372(4) . ?
C16 C17 1.384(4) . ?
C16 Br19 1.905(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(4) . ?
C18 H18 0.9500 . ?
N20 C21 1.400(3) . ?
C21 C22 1.399(4) . ?
C21 C26 1.401(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.390(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.385(4) . ?
C24 C25 1.383(4) . ?
C24 Br27 1.903(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.388(4) . ?
C26 H26 0.9500 . ?

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
C2 N1 C9 112.9(2) . . ?
C8 N1 C2 126.3(2) . . ?
C8 N1 C9 120.6(2) . . ?
N1 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
N3 C2 N1 110.5(2) . . ?
N3 C2 H2A 109.6 . . ?
N3 C2 H2B 109.6 . . ?
C2 N3 C11 111.5(2) . . ?
C4 N3 C2 121.6(2) . . ?
C4 N3 C11 117.0(2) . . ?
N3 C4 S5 114.89(19) . . ?
N12 C4 N3 121.4(2) . . ?
N12 C4 S5 123.3(2) . . ?
C4 S5 S6 101.74(8) . . ?
S7 S6 S5 110.45(4) . . ?
C8 S7 S6 101.61(8) . . ?
N1 C8 S7 115.81(18) . . ?
N20 C8 N1 120.3(2) . . ?
N20 C8 S7 123.8(2) . . ?
N1 C9 H9A 109.8 . . ?
N1 C9 H9B 109.8 . . ?
N1 C9 C10 109.4(2) . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C9 C10 C11 111.1(2) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
N3 C11 C10 110.0(2) . . ?
N3 C11 H11A 109.7 . . ?
N3 C11 H11B 109.7 . . ?
C10 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C4 N12 C13 122.6(2) . . ?
C14 C13 N12 119.6(2) . . ?
C14 C13 C18 119.2(2) . . ?
C18 C13 N12 121.1(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 121.8(2) . . ?
C15 C16 Br19 118.3(2) . . ?
C17 C16 Br19 119.9(2) . . ?
C16 C17 H17 120.7 . . ?
C16 C17 C18 118.6(2) . . ?
C18 C17 H17 120.7 . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.7(2) . . ?
C17 C18 H18 119.7 . . ?
C8 N20 C21 125.1(2) . . ?
N20 C21 C26 123.5(2) . . ?
C22 C21 N20 117.3(2) . . ?
C22 C21 C26 118.7(2) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 120.9(2) . . ?
C23 C22 H22 119.5 . . ?
C22 C23 H23 120.6 . . ?
C24 C23 C22 118.8(2) . . ?
C24 C23 H23 120.6 . . ?
C23 C24 Br27 120.06(19) . . ?
C25 C24 C23 121.6(2) . . ?
C25 C24 Br27 118.3(2) . . ?
C24 C25 H25 120.4 . . ?
C24 C25 C26 119.2(2) . . ?
C26 C25 H25 120.4 . . ?
C21 C26 H26 119.7 . . ?
C25 C26 C21 120.6(2) . . ?
C25 C26 H26 119.7 . . ?

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
N1 C2 N3 C4 85.2(3) . . . . ?
N1 C2 N3 C11 -59.4(3) . . . . ?
N1 C8 N20 C21 177.8(2) . . . . ?
N1 C9 C10 C11 52.6(3) . . . . ?
C2 N1 C8 S7 14.7(3) . . . . ?
C2 N1 C8 N20 -166.3(3) . . . . ?
C2 N1 C9 C10 -55.8(3) . . . . ?
C2 N3 C4 S5 29.3(3) . . . . ?
C2 N3 C4 N12 -157.7(2) . . . . ?
C2 N3 C11 C10 56.9(3) . . . . ?
N3 C4 S5 S6 -85.98(18) . . . . ?
N3 C4 N12 C13 -178.2(2) . . . . ?
C4 N3 C11 C10 -89.5(3) . . . . ?
C4 N12 C13 C14 114.1(3) . . . . ?
C4 N12 C13 C18 -69.9(3) . . . . ?
S5 C4 N12 C13 -5.9(4) . . . . ?
S6 S7 C8 N1 63.8(2) . . . . ?
S6 S7 C8 N20 -115.1(2) . . . . ?
S7 C8 N20 C21 -3.3(4) . . . . ?
C8 N1 C2 N3 -125.6(3) . . . . ?
C8 N1 C9 C10 128.9(3) . . . . ?
C8 N20 C21 C22 140.3(3) . . . . ?
C8 N20 C21 C26 -47.1(4) . . . . ?
C9 N1 C2 N3 59.4(3) . . . . ?
C9 N1 C8 S7 -170.7(2) . . . . ?
C9 N1 C8 N20 8.3(4) . . . . ?
C9 C10 C11 N3 -53.6(3) . . . . ?
C11 N3 C4 S5 172.04(17) . . . . ?
C11 N3 C4 N12 -15.0(4) . . . . ?
N12 C4 S5 S6 101.2(2) . . . . ?
N12 C13 C14 C15 179.7(2) . . . . ?
N12 C13 C18 C17 -179.0(2) . . . . ?
C13 C14 C15 C16 -1.5(4) . . . . ?
C14 C13 C18 C17 -3.0(4) . . . . ?
C14 C15 C16 C17 -1.4(4) . . . . ?
C14 C15 C16 Br19 176.3(2) . . . . ?
C15 C16 C17 C18 2.0(4) . . . . ?
C16 C17 C18 C13 0.2(4) . . . . ?
C18 C13 C14 C15 3.6(4) . . . . ?
Br19 C16 C17 C18 -175.6(2) . . . . ?
N20 C21 C22 C23 175.1(2) . . . . ?
N20 C21 C26 C25 -174.7(2) . . . . ?
C21 C22 C23 C24 -0.8(4) . . . . ?
C22 C21 C26 C25 -2.2(4) . . . . ?
C22 C23 C24 C25 -0.4(4) . . . . ?
C22 C23 C24 Br27 -178.5(2) . . . . ?
C23 C24 C25 C26 0.3(4) . . . . ?
C24 C25 C26 C21 1.0(4) . . . . ?
C26 C21 C22 C23 2.1(4) . . . . ?
Br27 C24 C25 C26 178.45(19) . . . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.634
_oxdiff_exptl_absorpt_empirical_full_min 0.543
