# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_HMM-7-OH
_database_code_depnum_ccdc_archive 'CCDC 1041069'
_audit_update_record             
;
2014-12-27 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;
_audit_creation_date             2014-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4973)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
'0.67(Br), 0.67(C23 H19 Br Cl N4 O S), 0.67(H2 O), 0.67(C H4 O)'
_chemical_formula_sum            'C16 H16.67 Br1.33 Cl0.67 N2.67 O2 S0.67'
_chemical_formula_weight         429.87
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H26 N3 S'
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'
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'
Br Br -0.6763 1.2805 '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'
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      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                   7.9404(8)
_cell_length_b                   11.6089(14)
_cell_length_c                   15.7240(18)
_cell_angle_alpha                71.877(10)
_cell_angle_beta                 79.537(9)
_cell_angle_gamma                78.741(10)
_cell_volume                     1339.6(3)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    3295
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7207
_cell_measurement_theta_min      2.9798
_shelx_estimated_absorpt_T_max   0.893
_shelx_estimated_absorpt_T_min   0.277
_exptl_absorpt_coefficient_mu    5.761
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8394
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.857
_diffrn_reflns_theta_min         2.982
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -51.00   35.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000 -150.0000 86

#__ type_ start__ end____ width___ exp.time_
  2 omega  -67.00  -41.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  125.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -66.00   32.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   19.0000  150.0000 98

#__ type_ start__ end____ width___ exp.time_
  4 omega  -85.00  -36.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -50.0000  -60.0000 49

#__ type_ start__ end____ width___ exp.time_
  5 omega   25.00  104.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  -60.0000 79

#__ type_ start__ end____ width___ exp.time_
  6 omega   82.00  115.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
  7 omega   11.00   58.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  120.0000 47

#__ type_ start__ end____ width___ exp.time_
  8 omega   53.00  113.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 60

#__ type_ start__ end____ width___ exp.time_
  9 omega   25.00   71.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   90.0000 46

#__ type_ start__ end____ width___ exp.time_
 10 omega   77.00  105.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
 11 omega  -12.00   68.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -30.0000 80

#__ type_ start__ end____ width___ exp.time_
 12 omega   37.00  111.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 74

#__ type_ start__ end____ width___ exp.time_
 13 omega   45.00   90.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 45

#__ type_ start__ end____ width___ exp.time_
 14 omega   40.00   92.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 52

#__ type_ start__ end____ width___ exp.time_
 15 omega   44.00   88.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   41.00  132.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000  -90.0000 91

#__ type_ start__ end____ width___ exp.time_
 17 omega   37.00   75.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   90.0000 38

#__ type_ start__ end____ width___ exp.time_
 18 omega   65.00   92.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 19 omega   48.00  113.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 65

#__ type_ start__ end____ width___ exp.time_
 20 omega   97.00  164.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000    0.0000 67

#__ type_ start__ end____ width___ exp.time_
 21 omega   63.00   96.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -90.0000 33

#__ type_ start__ end____ width___ exp.time_
 22 omega   50.00   94.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
 23 omega   38.00   64.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega   45.00  176.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -12.0000  -30.0000 131

#__ type_ start__ end____ width___ exp.time_
 25 omega   36.00   63.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 26 omega   51.00  116.00   1.0000    3.9700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 65
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1247698000
_diffrn_orient_matrix_UB_12      -0.0441220000
_diffrn_orient_matrix_UB_13      0.0719801000
_diffrn_orient_matrix_UB_21      0.1421526000
_diffrn_orient_matrix_UB_22      0.0623332000
_diffrn_orient_matrix_UB_23      -0.0696173000
_diffrn_orient_matrix_UB_31      -0.0634719000
_diffrn_orient_matrix_UB_32      0.1187633000
_diffrn_orient_matrix_UB_33      0.0279572000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3624
_reflns_number_total             4826
_reflns_odcompleteness_completeness 96.02
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.713
_refine_diff_density_min         -1.292
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       0.0015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4826
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0640
_refine_ls_restrained_S_all      1.192
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1045P)²+2.8972P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1851
_refine_ls_wR_factor_ref         0.2408
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), N2(H2), C14(H14), C21(H21), C22(H22), C18(H18), C2(H2A), C13(H13),
 C19(H19), C11(H11), C1(H1B), C4(H4), C3(H3)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C1S(H1SA,H1SB,H1SC)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1S(H1S)
;
_atom_sites_solution_hydrogens   mixed
_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
Br1C Br 0.31421(10) 0.51653(7) 0.17057(6) 0.0648(3) Uani 1 1 d . . . . .
Br1 Br 0.28858(13) 0.56747(10) 0.39475(7) 0.0812(4) Uani 1 1 d . . . . .
S1 S 0.0676(3) 0.64462(16) 0.93497(13) 0.0612(5) Uani 1 1 d . . . . .
Cl1 Cl 0.2574(5) 1.1838(3) 0.5690(2) 0.1241(12) Uani 1 1 d . . . . .
O1 O 0.3637(6) 0.7180(4) 0.7720(4) 0.0606(13) Uani 1 1 d . . . . .
H1 H 0.4421 0.6601 0.7827 0.091 Uiso 1 1 calc GR . . . .
O1W O 0.4036(10) 0.3751(7) 0.0130(5) 0.090(2) Uani 1 1 d . . . . .
H1WA H 0.3749 0.3972 0.0610 0.134 Uiso 1 1 d G . . . .
H1WB H 0.5134 0.3608 0.0025 0.134 Uiso 1 1 d G . . . .
N4 N 0.0708(7) 0.7765(5) 0.7685(4) 0.0487(13) Uani 1 1 d . . . . .
N1 N -0.1965(8) 0.9893(5) 0.9738(4) 0.0586(15) Uani 1 1 d . . . . .
H1A H -0.1495 1.0537 0.9453 0.070 Uiso 1 1 calc R . . . .
C10 C 0.0387(8) 0.8850(6) 0.6941(5) 0.0491(15) Uani 1 1 d . . . . .
N3 N -0.0843(8) 0.8831(5) 0.8667(4) 0.0578(15) Uani 1 1 d . . . . .
N2 N -0.2657(7) 0.8068(5) 1.0063(4) 0.0542(14) Uani 1 1 d . . . . .
H2 H -0.2712 0.7354 1.0023 0.065 Uiso 1 1 calc R . . . .
C20 C 0.2708(10) 0.5951(7) 0.5059(6) 0.0614(18) Uani 1 1 d . . . . .
C15 C -0.1120(9) 0.9073(6) 0.6556(5) 0.0509(15) Uani 1 1 d . . . . .
C9 C 0.2139(8) 0.6759(6) 0.7626(5) 0.0492(15) Uani 1 1 d . . . . .
C14 C -0.1487(11) 1.0196(7) 0.5920(5) 0.0653(19) Uani 1 1 d . . . . .
H14 H -0.2511 1.0376 0.5666 0.078 Uiso 1 1 calc R . . . .
C5 C -0.3518(9) 0.8571(7) 1.0769(5) 0.0565(17) Uani 1 1 d . . . . .
C21 C 0.3736(10) 0.6670(8) 0.5219(6) 0.067(2) Uani 1 1 d . . . . .
H21 H 0.4570 0.7007 0.4759 0.080 Uiso 1 1 calc R . . . .
C8 C 0.1641(10) 0.5727(6) 0.8477(5) 0.0576(17) Uani 1 1 d . . . . .
H8A H 0.2660 0.5148 0.8659 0.069 Uiso 1 1 calc R . . . .
H8B H 0.0823 0.5291 0.8360 0.069 Uiso 1 1 calc R . . . .
C22 C 0.3565(10) 0.6904(8) 0.6035(6) 0.069(2) Uani 1 1 d . . . . .
H22 H 0.4301 0.7384 0.6115 0.083 Uiso 1 1 calc R . . . .
C18 C 0.1269(10) 0.5729(7) 0.6596(6) 0.066(2) Uani 1 1 d . . . . .
H18 H 0.0411 0.5418 0.7051 0.079 Uiso 1 1 calc R . . . .
C7 C 0.0048(9) 0.7833(6) 0.8548(5) 0.0506(15) Uani 1 1 d . . . . .
C23 C -0.3081(9) 0.9737(7) 1.0557(5) 0.0548(16) Uani 1 1 d . . . . .
C12 C 0.1142(12) 1.0774(7) 0.6024(6) 0.069(2) Uani 1 1 d . . . . .
C17 C 0.2327(8) 0.6447(6) 0.6749(5) 0.0509(15) Uani 1 1 d . . . . .
C16 C -0.2325(10) 0.8133(8) 0.6799(7) 0.069(2) Uani 1 1 d . . . . .
H16A H -0.1760 0.7440 0.6594 0.104 Uiso 1 1 calc GR . . . .
H16B H -0.3354 0.8487 0.6515 0.104 Uiso 1 1 calc GR . . . .
H16C H -0.2630 0.7874 0.7442 0.104 Uiso 1 1 calc GR . . . .
C2 C -0.4793(12) 1.0011(11) 1.1888(7) 0.087(3) Uani 1 1 d . . . . .
H2A H -0.5216 1.0483 1.2284 0.105 Uiso 1 1 calc R . . . .
C6 C -0.1755(8) 0.8890(6) 0.9475(5) 0.0498(15) Uani 1 1 d . . . . .
C13 C -0.0358(12) 1.1055(7) 0.5657(5) 0.071(2) Uani 1 1 d . . . . .
H13 H -0.0626 1.1808 0.5237 0.085 Uiso 1 1 calc R . . . .
C19 C 0.1469(11) 0.5467(8) 0.5774(6) 0.070(2) Uani 1 1 d . . . . .
H19 H 0.0768 0.4961 0.5698 0.084 Uiso 1 1 calc R . . . .
C11 C 0.1542(10) 0.9688(6) 0.6688(5) 0.0592(18) Uani 1 1 d . . . . .
H11 H 0.2549 0.9528 0.6955 0.071 Uiso 1 1 calc R . . . .
C1 C -0.3693(11) 1.0464(8) 1.1104(7) 0.075(2) Uani 1 1 d . . . . .
H1B H -0.3389 1.1243 1.0961 0.090 Uiso 1 1 calc R . . . .
C4 C -0.4620(11) 0.8103(9) 1.1534(7) 0.076(2) Uani 1 1 d . . . . .
H4 H -0.4912 0.7322 1.1672 0.091 Uiso 1 1 calc R . . . .
C3 C -0.5261(12) 0.8850(11) 1.2081(8) 0.093(3) Uani 1 1 d . . . . .
H3 H -0.6031 0.8574 1.2595 0.112 Uiso 1 1 calc R . . . .
O1S O 0.0725(8) 0.7924(5) 0.1205(4) 0.0749(16) Uani 1 1 d . . . . .
H1S H 0.1452 0.7313 0.1218 0.112 Uiso 1 1 calc GR . . . .
C1S C -0.0048(13) 0.7899(9) 0.2106(6) 0.083(3) Uani 1 1 d . . . . .
H1SA H -0.0888 0.8620 0.2092 0.124 Uiso 1 1 calc GR . . . .
H1SB H 0.0832 0.7877 0.2459 0.124 Uiso 1 1 calc GR . . . .
H1SC H -0.0607 0.7184 0.2371 0.124 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
Br1 C20 1.848(8) . ?
S1 C8 1.802(8) . ?
S1 C7 1.755(6) . ?
Cl1 C12 1.738(8) . ?
O1 H1 0.8200 . ?
O1 C9 1.419(8) . ?
O1W H1WA 0.8502 . ?
O1W H1WB 0.8503 . ?
N4 C10 1.444(8) . ?
N4 C9 1.474(8) . ?
N4 C7 1.384(9) . ?
N1 H1A 0.8600 . ?
N1 C23 1.407(10) . ?
N1 C6 1.324(9) . ?
C10 C15 1.382(9) . ?
C10 C11 1.386(9) . ?
N3 C7 1.283(9) . ?
N3 C6 1.358(9) . ?
N2 H2 0.8600 . ?
N2 C5 1.420(10) . ?
N2 C6 1.325(8) . ?
C20 C21 1.378(11) . ?
C20 C19 1.404(12) . ?
C15 C14 1.389(10) . ?
C15 C16 1.506(10) . ?
C9 C8 1.543(9) . ?
C9 C17 1.507(10) . ?
C14 H14 0.9300 . ?
C14 C13 1.388(12) . ?
C5 C23 1.386(10) . ?
C5 C4 1.380(12) . ?
C21 H21 0.9300 . ?
C21 C22 1.371(12) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C22 H22 0.9300 . ?
C22 C17 1.393(10) . ?
C18 H18 0.9300 . ?
C18 C17 1.389(10) . ?
C18 C19 1.392(12) . ?
C23 C1 1.352(11) . ?
C12 C13 1.357(13) . ?
C12 C11 1.388(10) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C2 H2A 0.9300 . ?
C2 C1 1.395(14) . ?
C2 C3 1.396(15) . ?
C13 H13 0.9300 . ?
C19 H19 0.9300 . ?
C11 H11 0.9300 . ?
C1 H1B 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.372(14) . ?
C3 H3 0.9300 . ?
O1S H1S 0.8200 . ?
O1S C1S 1.432(11) . ?
C1S H1SA 0.9600 . ?
C1S H1SB 0.9600 . ?
C1S H1SC 0.9600 . ?

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
C7 S1 C8 91.5(3) . . ?
C9 O1 H1 109.5 . . ?
H1WA O1W H1WB 109.5 . . ?
C10 N4 C9 123.1(5) . . ?
C7 N4 C10 117.9(5) . . ?
C7 N4 C9 115.6(5) . . ?
C23 N1 H1A 125.4 . . ?
C6 N1 H1A 125.4 . . ?
C6 N1 C23 109.2(6) . . ?
C15 C10 N4 119.5(6) . . ?
C15 C10 C11 122.0(6) . . ?
C11 C10 N4 118.3(6) . . ?
C7 N3 C6 122.3(6) . . ?
C5 N2 H2 126.0 . . ?
C6 N2 H2 126.0 . . ?
C6 N2 C5 108.1(6) . . ?
C21 C20 Br1 122.1(6) . . ?
C21 C20 C19 116.7(8) . . ?
C19 C20 Br1 121.2(6) . . ?
C10 C15 C14 117.8(7) . . ?
C10 C15 C16 121.8(6) . . ?
C14 C15 C16 120.4(7) . . ?
O1 C9 N4 105.2(5) . . ?
O1 C9 C8 109.9(6) . . ?
O1 C9 C17 111.8(6) . . ?
N4 C9 C8 102.2(5) . . ?
N4 C9 C17 112.0(5) . . ?
C17 C9 C8 114.9(6) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 C15 121.4(7) . . ?
C13 C14 H14 119.3 . . ?
C23 C5 N2 106.6(6) . . ?
C4 C5 N2 131.3(7) . . ?
C4 C5 C23 122.1(8) . . ?
C20 C21 H21 119.0 . . ?
C22 C21 C20 121.9(8) . . ?
C22 C21 H21 119.0 . . ?
S1 C8 H8A 110.4 . . ?
S1 C8 H8B 110.4 . . ?
C9 C8 S1 106.8(5) . . ?
C9 C8 H8A 110.4 . . ?
C9 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
C21 C22 H22 118.9 . . ?
C21 C22 C17 122.2(7) . . ?
C17 C22 H22 118.9 . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.2(7) . . ?
C19 C18 H18 119.4 . . ?
N4 C7 S1 110.5(5) . . ?
N3 C7 S1 129.5(6) . . ?
N3 C7 N4 120.0(6) . . ?
C5 C23 N1 105.8(6) . . ?
C1 C23 N1 132.9(8) . . ?
C1 C23 C5 121.3(8) . . ?
C13 C12 Cl1 119.0(6) . . ?
C13 C12 C11 122.3(7) . . ?
C11 C12 Cl1 118.6(7) . . ?
C22 C17 C9 120.7(7) . . ?
C18 C17 C9 122.7(6) . . ?
C18 C17 C22 116.6(8) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 C2 H2A 119.9 . . ?
C1 C2 C3 120.1(9) . . ?
C3 C2 H2A 119.9 . . ?
N1 C6 N3 121.3(6) . . ?
N1 C6 N2 110.4(7) . . ?
N2 C6 N3 128.1(6) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 C14 118.7(7) . . ?
C12 C13 H13 120.6 . . ?
C20 C19 H19 119.3 . . ?
C18 C19 C20 121.3(7) . . ?
C18 C19 H19 119.3 . . ?
C10 C11 C12 117.7(7) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
C23 C1 C2 118.0(9) . . ?
C23 C1 H1B 121.0 . . ?
C2 C1 H1B 121.0 . . ?
C5 C4 H4 121.8 . . ?
C3 C4 C5 116.5(9) . . ?
C3 C4 H4 121.8 . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 121.9(10) . . ?
C4 C3 H3 119.0 . . ?
C1S O1S H1S 109.5 . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?

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
Br1 C20 C21 C22 177.9(6) . . . . ?
Br1 C20 C19 C18 -176.4(6) . . . . ?
Cl1 C12 C13 C14 179.4(7) . . . . ?
Cl1 C12 C11 C10 -179.7(6) . . . . ?
O1 C9 C8 S1 75.0(6) . . . . ?
O1 C9 C17 C22 -19.1(8) . . . . ?
O1 C9 C17 C18 162.8(6) . . . . ?
N4 C10 C15 C14 172.2(7) . . . . ?
N4 C10 C15 C16 -8.8(10) . . . . ?
N4 C10 C11 C12 -174.8(7) . . . . ?
N4 C9 C8 S1 -36.3(6) . . . . ?
N4 C9 C17 C22 98.7(7) . . . . ?
N4 C9 C17 C18 -79.5(8) . . . . ?
N1 C23 C1 C2 -179.5(8) . . . . ?
C10 N4 C9 O1 78.8(7) . . . . ?
C10 N4 C9 C8 -166.3(6) . . . . ?
C10 N4 C9 C17 -42.8(8) . . . . ?
C10 N4 C7 S1 -177.0(4) . . . . ?
C10 N4 C7 N3 1.2(9) . . . . ?
C10 C15 C14 C13 1.9(12) . . . . ?
N2 C5 C23 N1 -0.5(7) . . . . ?
N2 C5 C23 C1 -179.7(7) . . . . ?
N2 C5 C4 C3 -178.9(8) . . . . ?
C20 C21 C22 C17 -1.0(13) . . . . ?
C15 C10 C11 C12 -0.3(12) . . . . ?
C15 C14 C13 C12 0.9(13) . . . . ?
C9 N4 C10 C15 114.6(7) . . . . ?
C9 N4 C10 C11 -70.7(9) . . . . ?
C9 N4 C7 S1 -17.0(7) . . . . ?
C9 N4 C7 N3 161.2(6) . . . . ?
C5 N2 C6 N1 -0.4(8) . . . . ?
C5 N2 C6 N3 -174.8(6) . . . . ?
C5 C23 C1 C2 -0.5(12) . . . . ?
C5 C4 C3 C2 -1.6(14) . . . . ?
C21 C20 C19 C18 1.5(12) . . . . ?
C21 C22 C17 C9 -177.9(7) . . . . ?
C21 C22 C17 C18 0.4(11) . . . . ?
C8 S1 C7 N4 -6.1(5) . . . . ?
C8 S1 C7 N3 175.9(7) . . . . ?
C8 C9 C17 C22 -145.3(7) . . . . ?
C8 C9 C17 C18 36.5(9) . . . . ?
C7 S1 C8 C9 25.5(5) . . . . ?
C7 N4 C10 C15 -87.0(8) . . . . ?
C7 N4 C10 C11 87.7(8) . . . . ?
C7 N4 C9 O1 -80.0(6) . . . . ?
C7 N4 C9 C8 34.8(7) . . . . ?
C7 N4 C9 C17 158.4(5) . . . . ?
C7 N3 C6 N1 147.4(7) . . . . ?
C7 N3 C6 N2 -38.8(11) . . . . ?
C23 N1 C6 N3 174.9(6) . . . . ?
C23 N1 C6 N2 0.0(8) . . . . ?
C23 C5 C4 C3 -0.3(12) . . . . ?
C17 C9 C8 S1 -157.9(5) . . . . ?
C17 C18 C19 C20 -2.2(13) . . . . ?
C16 C15 C14 C13 -177.1(8) . . . . ?
C6 N1 C23 C5 0.3(8) . . . . ?
C6 N1 C23 C1 179.4(8) . . . . ?
C6 N3 C7 S1 -13.3(10) . . . . ?
C6 N3 C7 N4 168.8(6) . . . . ?
C6 N2 C5 C23 0.6(8) . . . . ?
C6 N2 C5 C4 179.3(8) . . . . ?
C13 C12 C11 C10 3.3(13) . . . . ?
C19 C20 C21 C22 0.1(12) . . . . ?
C19 C18 C17 C9 179.4(7) . . . . ?
C19 C18 C17 C22 1.2(11) . . . . ?
C11 C10 C15 C14 -2.2(11) . . . . ?
C11 C10 C15 C16 176.8(8) . . . . ?
C11 C12 C13 C14 -3.6(13) . . . . ?
C1 C2 C3 C4 2.4(15) . . . . ?
C4 C5 C23 N1 -179.4(7) . . . . ?
C4 C5 C23 C1 1.4(12) . . . . ?
C3 C2 C1 C23 -1.3(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
