# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_HB_B1_0003
_database_code_depnum_ccdc_archive 'CCDC 2164409'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2022-04-04 deposited with the CCDC.	2022-12-15 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2018/1

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.0  (Andrew D. Bond, July 2015)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Lisa Sharma'
_cambridge_user_crsid            ls780
_cambridge_supervisor_name       'Hugo Bronstein'
_cambridge_supervisor_crsid      hab60
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             LS166
_cambridge_data_id               HB_B1_0003
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 N2 O2 S2'
_chemical_formula_sum            'C24 H26 N2 O2 S2'
_chemical_formula_weight         438.59

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'
O O 0.0492 0.0322 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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                   28.3920(9)
_cell_length_b                   8.9830(3)
_cell_length_c                   19.2814(6)
_cell_angle_alpha                90
_cell_angle_beta                 117.135(2)
_cell_angle_gamma                90
_cell_volume                     4376.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    8707
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      66.76

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             1856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.389
_shelx_estimated_absorpt_T_min   0.622
_shelx_estimated_absorpt_T_max   0.870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6216
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19770
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.498
_diffrn_reflns_theta_max         66.829
_diffrn_reflns_theta_full        66.829
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3887
_reflns_number_gt                3089
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.

#================================================================================
INTENSITY STATISTICS FOR DATASET # 1  HB_B1_0003_0m.hkl
#================================================================================
 Resolution   #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma

  Inf - 3.61      63     63    100.0     9.41     90.30   63.33  0.0255  0.0116
 3.61 - 2.36     145    145    100.0    10.77     37.76   51.75  0.0231  0.0117
 2.36 - 1.85     207    207    100.0     9.60     19.49   35.84  0.0465  0.0189
 1.85 - 1.61     211    211    100.0     8.27     12.72   28.51  0.0615  0.0221
 1.61 - 1.45     224    224    100.0     7.01     10.10   30.18  0.0601  0.0224
 1.45 - 1.35     195    196     99.5     4.59      7.44   21.81  0.0487  0.0311
 1.35 - 1.26     219    219    100.0     4.67      5.92   21.54  0.0458  0.0335
 1.26 - 1.20     191    191    100.0     4.74      6.09   20.04  0.0490  0.0336
 1.20 - 1.14     233    233    100.0     4.72      5.94   21.11  0.0491  0.0341
 1.14 - 1.10     192    192    100.0     4.70      4.60   16.43  0.0548  0.0404
 1.10 - 1.06     211    211    100.0     4.44      4.65   16.16  0.0546  0.0423
 1.06 - 1.03     189    189    100.0     4.42      3.32   13.80  0.0721  0.0530
 1.03 - 0.99     274    275     99.6     3.93      3.30   13.14  0.0737  0.0588
 0.99 - 0.97     165    165    100.0     3.87      2.05    9.30  0.0984  0.0779
 0.97 - 0.94     258    258    100.0     3.91      1.80    9.51  0.1058  0.0798
 0.94 - 0.92     200    200    100.0     3.89      1.75    9.84  0.1027  0.0770
 0.92 - 0.90     202    202    100.0     3.83      1.36    8.58  0.1201  0.0915
 0.90 - 0.88     223    224     99.6     3.39      1.33    8.38  0.1096  0.1037
 0.88 - 0.87     134    134    100.0     3.23      1.33    8.26  0.1217  0.1016
 0.87 - 0.85     261    261    100.0     3.14      1.25    7.59  0.1243  0.1037
 0.85 - 0.84     157    162     96.9     2.91      1.32    8.37  0.1156  0.0988
#--------------------------------------------------------------------------------
 0.94 - 0.84    1177   1183     99.5     3.41      1.39    8.47  0.1144  0.0951
  Inf - 0.84    4154   4162     99.8     5.00      7.53   18.33  0.0426  0.0279
#================================================================================
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0747P)²+9.1006P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3887
_refine_ls_number_parameters     290
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1547
_refine_ls_wR_factor_gt          0.1440
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.061

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
S1 S 0.41484(4) 0.03940(10) 0.96547(4) 0.0466(3) Uani 1 1 d . . . . .
S2 S 0.26089(3) 0.45306(10) 0.48574(4) 0.0442(2) Uani 1 1 d . . . . .
O1 O 0.42477(9) 0.1346(3) 0.68929(12) 0.0464(6) Uani 1 1 d . . . . .
O2 O 0.27694(8) 0.4304(3) 0.78243(12) 0.0410(5) Uani 1 1 d . . . . .
N1 N 0.41686(10) 0.1457(3) 0.80440(14) 0.0370(6) Uani 1 1 d . . . . .
N2 N 0.28578(9) 0.4270(3) 0.66844(13) 0.0303(5) Uani 1 1 d . . . . .
C1 C 0.40042(11) 0.1780(4) 0.72418(16) 0.0348(7) Uani 1 1 d . . . . .
C2 C 0.38169(11) 0.2075(3) 0.82872(16) 0.0303(6) Uani 1 1 d . . . . .
C3 C 0.34370(11) 0.2834(3) 0.76651(15) 0.0284(6) Uani 1 1 d . . . . .
C4 C 0.29942(10) 0.3833(3) 0.74590(15) 0.0303(6) Uani 1 1 d . . . . .
C5 C 0.31781(10) 0.3565(3) 0.64106(15) 0.0280(6) Uani 1 1 d . . . . .
C6 C 0.35376(10) 0.2690(3) 0.70125(15) 0.0295(6) Uani 1 1 d . . . . .
C7 C 0.38589(11) 0.1908(3) 0.90595(16) 0.0317(6) Uani 1 1 d . . . . .
C8 C 0.36542(12) 0.2857(4) 0.94067(17) 0.0397(7) Uani 1 1 d . . . . .
H8A H 0.347576 0.375501 0.917315 0.048 Uiso 1 1 calc R U . . .
C9 C 0.37349(13) 0.2366(4) 1.01458(18) 0.0460(8) Uani 1 1 d . . . . .
H9A H 0.361905 0.290388 1.046412 0.055 Uiso 1 1 calc R U . . .
C10 C 0.39935(13) 0.1055(4) 1.03567(17) 0.0442(8) Uani 1 1 d . . . . .
H10A H 0.407875 0.056056 1.083499 0.053 Uiso 1 1 calc R U . . .
C11 C 0.31222(11) 0.3679(3) 0.56313(16) 0.0323(6) Uani 1 1 d . . . . .
C12 C 0.34660(12) 0.2957(4) 0.53748(15) 0.0343(7) Uani 1 1 d . . . . .
H12A H 0.377935 0.243042 0.570363 0.041 Uiso 1 1 calc R U . . .
C13 C 0.32721(15) 0.3140(5) 0.4568(2) 0.0526(9) Uani 1 1 d . . . . .
H13A H 0.344340 0.272993 0.428786 0.063 Uiso 1 1 calc R U . . .
C14 C 0.28235(15) 0.3944(4) 0.42223(18) 0.0476(9) Uani 1 1 d . . . . .
H14A H 0.264776 0.415572 0.368009 0.057 Uiso 1 1 calc R U . . .
C15 C 0.47323(11) 0.1156(4) 0.85548(17) 0.0369(7) Uani 1 1 d D . . . .
H15A H 0.490408 0.085976 0.822976 0.044 Uiso 1 1 calc R U . A 1
H15B H 0.476214 0.030846 0.890095 0.044 Uiso 1 1 calc R U . A 1
C16 C 0.50260(14) 0.2490(4) 0.9054(2) 0.0472(8) Uani 0.515(11) 1 d D . P B 1
H16A H 0.485086 0.271011 0.938381 0.057 Uiso 0.515(11) 1 calc R U P B 1
H16B H 0.538505 0.212559 0.941078 0.057 Uiso 0.515(11) 1 calc R U P B 1
C17 C 0.5105(3) 0.3984(7) 0.8755(6) 0.047(2) Uani 0.515(11) 1 d D U P B 1
H17A H 0.544206 0.443246 0.914052 0.056 Uiso 0.515(11) 1 calc R U P B 1
H17B H 0.512787 0.384038 0.826206 0.056 Uiso 0.515(11) 1 calc R U P B 1
C18 C 0.4651(3) 0.5024(7) 0.8617(5) 0.053(2) Uani 0.515(11) 1 d D U P B 1
H18A H 0.460715 0.507764 0.909766 0.063 Uiso 0.515(11) 1 calc R U P B 1
H18B H 0.432017 0.460867 0.819845 0.063 Uiso 0.515(11) 1 calc R U P B 1
C19 C 0.47333(19) 0.6608(5) 0.8387(3) 0.0878(16) Uani 0.515(11) 1 d D . P B 1
H19A H 0.500638 0.715623 0.883554 0.105 Uiso 0.515(11) 1 calc R U P B 1
H19B H 0.483137 0.659438 0.795549 0.105 Uiso 0.515(11) 1 calc R U P B 1
C16A C 0.50260(14) 0.2490(4) 0.9054(2) 0.0472(8) Uani 0.485(11) 1 d D . P B 2
H16C H 0.541353 0.233235 0.929559 0.057 Uiso 0.485(11) 1 calc R U P B 2
H16D H 0.492030 0.266397 0.947047 0.057 Uiso 0.485(11) 1 calc R U P B 2
C17A C 0.4859(4) 0.3833(7) 0.8472(4) 0.045(2) Uani 0.485(11) 1 d D U P B 2
H17C H 0.502838 0.373405 0.812442 0.054 Uiso 0.485(11) 1 calc R U P B 2
H17D H 0.447080 0.382171 0.814393 0.054 Uiso 0.485(11) 1 calc R U P B 2
C18A C 0.5024(4) 0.5307(7) 0.8911(5) 0.066(3) Uani 0.485(11) 1 d D U P B 2
H18C H 0.494591 0.528000 0.936186 0.079 Uiso 0.485(11) 1 calc R U P B 2
H18D H 0.541008 0.544630 0.911301 0.079 Uiso 0.485(11) 1 calc R U P B 2
C19A C 0.47333(19) 0.6608(5) 0.8387(3) 0.0878(16) Uani 0.485(11) 1 d D . P B 2
H19C H 0.497528 0.746266 0.861793 0.105 Uiso 0.485(11) 1 calc R U P B 2
H19D H 0.474507 0.638957 0.789162 0.105 Uiso 0.485(11) 1 calc R U P B 2
C20 C 0.41888(18) 0.7263(7) 0.8131(4) 0.106(2) Uani 1 1 d D . . . .
H20A H 0.407033 0.698798 0.852379 0.127 Uiso 1 1 calc R U . B 1
H20B H 0.422178 0.836057 0.814091 0.127 Uiso 1 1 calc R U . B 1
C21 C 0.37736(17) 0.6836(5) 0.7367(3) 0.0728(12) Uani 1 1 d D . . . .
H21A H 0.374218 0.573722 0.734712 0.087 Uiso 1 1 calc R U . . .
H21B H 0.388212 0.714166 0.696735 0.087 Uiso 1 1 calc R U . . .
C22 C 0.32324(16) 0.7500(5) 0.7156(3) 0.0724(12) Uani 1 1 d D . . . .
H22A H 0.325733 0.859882 0.715414 0.087 Uiso 1 1 calc R U . . .
H22B H 0.312441 0.721776 0.755927 0.087 Uiso 1 1 calc R U . . .
C23 C 0.28114(17) 0.6980(4) 0.6364(2) 0.0590(10) Uani 1 1 d D . . . .
H23A H 0.254867 0.778869 0.613203 0.071 Uiso 1 1 calc R U . . .
H23B H 0.298191 0.682594 0.602152 0.071 Uiso 1 1 calc R U . . .
C24 C 0.25188(13) 0.5570(4) 0.63587(18) 0.0427(8) Uani 1 1 d D . . . .
H24A H 0.231902 0.574917 0.665823 0.051 Uiso 1 1 calc R U . . .
H24B H 0.225864 0.534575 0.581456 0.051 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
S1 C10 1.709(3) . ?
S1 C7 1.727(3) . ?
S2 C14 1.682(4) . ?
S2 C11 1.718(3) . ?
O1 C1 1.228(3) . ?
O2 C4 1.222(3) . ?
N1 C2 1.397(4) . ?
N1 C1 1.427(4) . ?
N1 C15 1.472(4) . ?
N2 C5 1.394(3) . ?
N2 C4 1.417(3) . ?
N2 C24 1.461(4) . ?
C1 C6 1.443(4) . ?
C2 C3 1.374(4) . ?
C2 C7 1.446(4) . ?
C3 C6 1.418(4) . ?
C3 C4 1.445(4) . ?
C5 C6 1.388(4) . ?
C5 C11 1.441(4) . ?
C7 C8 1.367(4) . ?
C8 C9 1.407(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.349(5) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.435(4) . ?
C12 C13 1.404(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.347(5) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 C16A 1.525(4) . ?
C15 C16 1.525(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.517(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.516(8) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.541(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.511(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C16A C17A 1.567(7) . ?
C16A H16C 0.9900 . ?
C16A H16D 0.9900 . ?
C17A C18A 1.526(8) . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C18A C19A 1.520(7) . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C19A C20 1.511(6) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C20 C21 1.457(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.521(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.522(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.512(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

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
C10 S1 C7 92.09(15) . . ?
C14 S2 C11 92.71(16) . . ?
C2 N1 C1 110.6(2) . . ?
C2 N1 C15 125.0(2) . . ?
C1 N1 C15 118.8(2) . . ?
C5 N2 C4 111.2(2) . . ?
C5 N2 C24 128.0(2) . . ?
C4 N2 C24 119.0(2) . . ?
O1 C1 N1 122.8(3) . . ?
O1 C1 C6 132.8(3) . . ?
N1 C1 C6 104.4(2) . . ?
C3 C2 N1 107.5(2) . . ?
C3 C2 C7 127.9(2) . . ?
N1 C2 C7 124.6(2) . . ?
C2 C3 C6 109.5(2) . . ?
C2 C3 C4 141.9(2) . . ?
C6 C3 C4 108.4(2) . . ?
O2 C4 N2 123.3(3) . . ?
O2 C4 C3 132.4(3) . . ?
N2 C4 C3 104.3(2) . . ?
C6 C5 N2 107.4(2) . . ?
C6 C5 C11 127.0(3) . . ?
N2 C5 C11 125.6(2) . . ?
C5 C6 C3 108.7(2) . . ?
C5 C6 C1 143.0(2) . . ?
C3 C6 C1 108.0(2) . . ?
C8 C7 C2 125.9(3) . . ?
C8 C7 S1 110.2(2) . . ?
C2 C7 S1 123.8(2) . . ?
C7 C8 C9 113.1(3) . . ?
C7 C8 H8A 123.5 . . ?
C9 C8 H8A 123.5 . . ?
C10 C9 C8 113.2(3) . . ?
C10 C9 H9A 123.4 . . ?
C8 C9 H9A 123.4 . . ?
C9 C10 S1 111.5(2) . . ?
C9 C10 H10A 124.3 . . ?
S1 C10 H10A 124.3 . . ?
C12 C11 C5 124.0(3) . . ?
C12 C11 S2 110.1(2) . . ?
C5 C11 S2 125.7(2) . . ?
C13 C12 C11 110.2(3) . . ?
C13 C12 H12A 124.9 . . ?
C11 C12 H12A 124.9 . . ?
C14 C13 C12 114.5(3) . . ?
C14 C13 H13A 122.7 . . ?
C12 C13 H13A 122.7 . . ?
C13 C14 S2 112.5(2) . . ?
C13 C14 H14A 123.7 . . ?
S2 C14 H14A 123.7 . . ?
N1 C15 C16A 113.1(3) . . ?
N1 C15 C16 113.1(3) . . ?
N1 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
N1 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C15 126.1(5) . . ?
C17 C16 H16A 105.8 . . ?
C15 C16 H16A 105.8 . . ?
C17 C16 H16B 105.8 . . ?
C15 C16 H16B 105.8 . . ?
H16A C16 H16B 106.2 . . ?
C18 C17 C16 110.5(5) . . ?
C18 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 C19 113.0(5) . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C20 C19 C18 100.7(5) . . ?
C20 C19 H19A 111.6 . . ?
C18 C19 H19A 111.6 . . ?
C20 C19 H19B 111.6 . . ?
C18 C19 H19B 111.6 . . ?
H19A C19 H19B 109.4 . . ?
C15 C16A C17A 104.7(4) . . ?
C15 C16A H16C 110.8 . . ?
C17A C16A H16C 110.8 . . ?
C15 C16A H16D 110.8 . . ?
C17A C16A H16D 110.8 . . ?
H16C C16A H16D 108.9 . . ?
C18A C17A C16A 110.8(6) . . ?
C18A C17A H17C 109.5 . . ?
C16A C17A H17C 109.5 . . ?
C18A C17A H17D 109.5 . . ?
C16A C17A H17D 109.5 . . ?
H17C C17A H17D 108.1 . . ?
C19A C18A C17A 111.2(6) . . ?
C19A C18A H18C 109.4 . . ?
C17A C18A H18C 109.4 . . ?
C19A C18A H18D 109.4 . . ?
C17A C18A H18D 109.4 . . ?
H18C C18A H18D 108.0 . . ?
C20 C19A C18A 132.9(6) . . ?
C20 C19A H19C 104.0 . . ?
C18A C19A H19C 104.0 . . ?
C20 C19A H19D 104.0 . . ?
C18A C19A H19D 104.0 . . ?
H19C C19A H19D 105.5 . . ?
C21 C20 C19 117.6(5) . . ?
C21 C20 C19A 117.6(5) . . ?
C21 C20 H20A 107.9 . . ?
C19 C20 H20A 107.9 . . ?
C21 C20 H20B 107.9 . . ?
C19 C20 H20B 107.9 . . ?
H20A C20 H20B 107.2 . . ?
C20 C21 C22 114.8(4) . . ?
C20 C21 H21A 108.6 . . ?
C22 C21 H21A 108.6 . . ?
C20 C21 H21B 108.6 . . ?
C22 C21 H21B 108.6 . . ?
H21A C21 H21B 107.5 . . ?
C21 C22 C23 112.5(3) . . ?
C21 C22 H22A 109.1 . . ?
C23 C22 H22A 109.1 . . ?
C21 C22 H22B 109.1 . . ?
C23 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C24 C23 C22 116.2(3) . . ?
C24 C23 H23A 108.2 . . ?
C22 C23 H23A 108.2 . . ?
C24 C23 H23B 108.2 . . ?
C22 C23 H23B 108.2 . . ?
H23A C23 H23B 107.4 . . ?
N2 C24 C23 114.5(3) . . ?
N2 C24 H24A 108.6 . . ?
C23 C24 H24A 108.6 . . ?
N2 C24 H24B 108.6 . . ?
C23 C24 H24B 108.6 . . ?
H24A C24 H24B 107.6 . . ?

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
C2 N1 C1 O1 -179.5(3) . . . . ?
C15 N1 C1 O1 25.6(5) . . . . ?
C2 N1 C1 C6 2.1(3) . . . . ?
C15 N1 C1 C6 -152.8(3) . . . . ?
C1 N1 C2 C3 -1.9(3) . . . . ?
C15 N1 C2 C3 151.1(3) . . . . ?
C1 N1 C2 C7 177.7(3) . . . . ?
C15 N1 C2 C7 -29.3(5) . . . . ?
N1 C2 C3 C6 0.9(3) . . . . ?
C7 C2 C3 C6 -178.7(3) . . . . ?
N1 C2 C3 C4 -172.0(4) . . . . ?
C7 C2 C3 C4 8.4(6) . . . . ?
C5 N2 C4 O2 179.9(3) . . . . ?
C24 N2 C4 O2 14.0(4) . . . . ?
C5 N2 C4 C3 1.8(3) . . . . ?
C24 N2 C4 C3 -164.1(3) . . . . ?
C2 C3 C4 O2 -6.2(7) . . . . ?
C6 C3 C4 O2 -179.1(3) . . . . ?
C2 C3 C4 N2 171.6(4) . . . . ?
C6 C3 C4 N2 -1.3(3) . . . . ?
C4 N2 C5 C6 -1.7(3) . . . . ?
C24 N2 C5 C6 162.6(3) . . . . ?
C4 N2 C5 C11 175.5(3) . . . . ?
C24 N2 C5 C11 -20.2(5) . . . . ?
N2 C5 C6 C3 0.7(3) . . . . ?
C11 C5 C6 C3 -176.3(3) . . . . ?
N2 C5 C6 C1 -172.0(4) . . . . ?
C11 C5 C6 C1 10.9(6) . . . . ?
C2 C3 C6 C5 -175.0(3) . . . . ?
C4 C3 C6 C5 0.4(3) . . . . ?
C2 C3 C6 C1 0.5(3) . . . . ?
C4 C3 C6 C1 175.8(3) . . . . ?
O1 C1 C6 C5 -7.0(7) . . . . ?
N1 C1 C6 C5 171.2(4) . . . . ?
O1 C1 C6 C3 -179.7(4) . . . . ?
N1 C1 C6 C3 -1.5(3) . . . . ?
C3 C2 C7 C8 -24.7(5) . . . . ?
N1 C2 C7 C8 155.8(3) . . . . ?
C3 C2 C7 S1 151.4(3) . . . . ?
N1 C2 C7 S1 -28.1(4) . . . . ?
C10 S1 C7 C8 -0.2(3) . . . . ?
C10 S1 C7 C2 -176.8(3) . . . . ?
C2 C7 C8 C9 177.0(3) . . . . ?
S1 C7 C8 C9 0.4(4) . . . . ?
C7 C8 C9 C10 -0.5(4) . . . . ?
C8 C9 C10 S1 0.4(4) . . . . ?
C7 S1 C10 C9 -0.1(3) . . . . ?
C6 C5 C11 C12 -4.6(5) . . . . ?
N2 C5 C11 C12 178.8(3) . . . . ?
C6 C5 C11 S2 168.8(2) . . . . ?
N2 C5 C11 S2 -7.8(4) . . . . ?
C14 S2 C11 C12 1.1(2) . . . . ?
C14 S2 C11 C5 -173.1(3) . . . . ?
C5 C11 C12 C13 173.1(3) . . . . ?
S2 C11 C12 C13 -1.2(3) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 S2 0.1(4) . . . . ?
C11 S2 C14 C13 -0.7(3) . . . . ?
C2 N1 C15 C16A -50.4(4) . . . . ?
C1 N1 C15 C16A 100.7(3) . . . . ?
C2 N1 C15 C16 -50.4(4) . . . . ?
C1 N1 C15 C16 100.7(3) . . . . ?
N1 C15 C16 C17 -62.5(5) . . . . ?
C15 C16 C17 C18 89.3(8) . . . . ?
C16 C17 C18 C19 174.6(6) . . . . ?
C17 C18 C19 C20 168.8(7) . . . . ?
N1 C15 C16A C17A -47.5(5) . . . . ?
C15 C16A C17A C18A 167.6(7) . . . . ?
C16A C17A C18A C19A -163.5(6) . . . . ?
C17A C18A C19A C20 81.7(10) . . . . ?
C18 C19 C20 C21 -76.9(7) . . . . ?
C18A C19A C20 C21 -98.7(9) . . . . ?
C19 C20 C21 C22 178.4(5) . . . . ?
C19A C20 C21 C22 178.4(5) . . . . ?
C20 C21 C22 C23 -178.3(5) . . . . ?
C21 C22 C23 C24 89.3(5) . . . . ?
C5 N2 C24 C23 -63.2(4) . . . . ?
C4 N2 C24 C23 100.1(3) . . . . ?
C22 C23 C24 N2 -58.1(4) . . . . ?

####################################################################### 
# 
# 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_HB_B1_0008
_database_code_depnum_ccdc_archive 'CCDC 2177219'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2022-06-06 deposited with the CCDC.	2022-12-15 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2018/1

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.0  (Andrew D. Bond, July 2015)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Lisa Sharma'
_cambridge_user_crsid            ls780
_cambridge_supervisor_name       'Hugo Bronstein'
_cambridge_supervisor_crsid      hab60
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             LS167
_cambridge_data_id               HB_B1_0008
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H24 Br2 N2 O2 S2'
_chemical_formula_sum            'C24 H24 Br2 N2 O2 S2'
_chemical_formula_weight         596.39

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'
O O 0.0492 0.0322 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0631(3)
_cell_length_b                   10.1990(4)
_cell_length_c                   11.4730(4)
_cell_angle_alpha                95.6730(14)
_cell_angle_beta                 98.5888(12)
_cell_angle_gamma                92.6598(13)
_cell_volume                     1156.37(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9427
_cell_measurement_theta_min      3.92
_cell_measurement_theta_max      66.94

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    6.342
_shelx_estimated_absorpt_T_min   0.450
_shelx_estimated_absorpt_T_max   0.786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5641
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13431
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.919
_diffrn_reflns_theta_max         66.937
_diffrn_reflns_theta_full        66.937
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4095
_reflns_number_gt                3637
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.

#===============================================================================
INTENSITY STATISTICS FOR DATASET # 1  HB_B1_0008_0m.hkl
#===============================================================================
 Resolution   #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#-------------------------------------------------------------------------------
  Inf - 3.37      62     62    100.0     3.77     43.43   48.17  0.0274  0.0206
 3.37 - 2.28     143    143    100.0     3.72     48.43   43.13  0.0268  0.0212
 2.28 - 1.81     205    205    100.0     4.19     28.86   38.40  0.0252  0.0190
 1.81 - 1.58     209    209    100.0     5.15     25.19   42.50  0.0263  0.0163
 1.58 - 1.43     205    205    100.0     4.86     16.14   38.11  0.0267  0.0179
 1.43 - 1.33     214    214    100.0     4.05     15.67   34.60  0.0248  0.0196
 1.33 - 1.25     202    202    100.0     4.20     16.02   34.96  0.0218  0.0193
 1.25 - 1.19     210    210    100.0     3.96     14.09   34.33  0.0233  0.0200
 1.19 - 1.13     222    223     99.6     3.88      8.51   28.13  0.0264  0.0236
 1.13 - 1.09     200    200    100.0     3.51      9.18   26.10  0.0307  0.0247
 1.09 - 1.05     227    227    100.0     3.73      7.30   25.44  0.0346  0.0255
 1.05 - 1.02     172    174     98.9     3.07      6.51   22.37  0.0288  0.0288
 1.02 - 0.99     221    224     98.7     2.48      6.66   20.45  0.0313  0.0317
 0.99 - 0.96     239    241     99.2     2.58      5.99   21.61  0.0262  0.0298
 0.96 - 0.94     178    178    100.0     2.58      6.00   20.61  0.0229  0.0304
 0.94 - 0.92     184    185     99.5     2.51      4.27   20.61  0.0294  0.0336
 0.92 - 0.90     224    225     99.6     2.45      4.92   19.40  0.0271  0.0318
 0.90 - 0.88     236    236    100.0     2.27      3.83   17.88  0.0316  0.0360
 0.88 - 0.86     238    242     98.3     2.02      3.58   16.12  0.0345  0.0388
 0.86 - 0.85     134    134    100.0     1.95      2.57   14.57  0.0458  0.0448
 0.85 - 0.84     170    184     92.4     1.64      2.49   12.58  0.0374  0.0473
#-------------------------------------------------------------------------------
 0.94 - 0.84    1186   1206     98.3     2.16      3.72   17.10  0.0315  0.0368
  Inf - 0.84    4095   4123     99.3     3.26     11.85   26.89  0.0265  0.0226
#===============================================================================
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0244P)²+0.5768P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00320(14)
_refine_ls_number_reflns         4095
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0231
_refine_ls_wR_factor_ref         0.0584
_refine_ls_wR_factor_gt          0.0564
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.069

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.89429(2) 0.31278(2) 0.98536(2) 0.03870(9) Uani 1 1 d . . . . .
Br2 Br -0.31565(2) 0.01040(2) 0.08248(2) 0.03585(9) Uani 1 1 d . . . . .
S1 S 0.59218(5) 0.28163(5) 0.87226(4) 0.02491(12) Uani 1 1 d . . . . .
S2 S -0.01356(5) 0.04846(5) 0.19320(4) 0.02426(11) Uani 1 1 d . . . . .
O1 O 0.05803(13) 0.23149(14) 0.65261(11) 0.0258(3) Uani 1 1 d . . . . .
O2 O 0.52226(13) 0.12319(13) 0.40795(12) 0.0252(3) Uani 1 1 d . . . . .
N1 N 0.28931(15) 0.24614(15) 0.71231(13) 0.0187(3) Uani 1 1 d . . . . .
N2 N 0.29177(14) 0.11376(14) 0.34789(13) 0.0176(3) Uani 1 1 d . . . . .
C1 C 0.17047(18) 0.21317(17) 0.62861(16) 0.0184(4) Uani 1 1 d . . . . .
C2 C 0.40414(17) 0.21610(16) 0.66214(15) 0.0165(4) Uani 1 1 d . . . . .
C3 C 0.36054(18) 0.16793(16) 0.54485(16) 0.0166(3) Uani 1 1 d . . . . .
C4 C 0.40950(18) 0.13261(17) 0.43427(16) 0.0184(4) Uani 1 1 d . . . . .
C5 C 0.17578(17) 0.12829(16) 0.39996(15) 0.0161(3) Uani 1 1 d . . . . .
C6 C 0.21863(17) 0.16450(16) 0.52043(15) 0.0162(4) Uani 1 1 d . . . . .
C7 C 0.54056(18) 0.23028(17) 0.72210(16) 0.0182(4) Uani 1 1 d . . . . .
C8 C 0.65108(19) 0.20440(18) 0.66752(17) 0.0222(4) Uani 1 1 d . . . . .
H8A H 0.644093 0.174402 0.585640 0.027 Uiso 1 1 calc R U . . .
C9 C 0.77518(19) 0.22628(18) 0.74364(17) 0.0237(4) Uani 1 1 d . . . . .
H9A H 0.860266 0.213393 0.719350 0.028 Uiso 1 1 calc R U . . .
C10 C 0.75798(19) 0.26798(18) 0.85581(18) 0.0242(4) Uani 1 1 d . . . . .
C11 C 0.03868(18) 0.10649(17) 0.34149(16) 0.0181(4) Uani 1 1 d . . . . .
C12 C -0.07105(19) 0.12784(18) 0.39792(17) 0.0222(4) Uani 1 1 d . . . . .
H12A H -0.063292 0.158359 0.479753 0.027 Uiso 1 1 calc R U . . .
C13 C -0.19579(19) 0.10045(18) 0.32366(17) 0.0231(4) Uani 1 1 d . . . . .
H13A H -0.280786 0.110934 0.348815 0.028 Uiso 1 1 calc R U . . .
C14 C -0.17889(19) 0.05714(18) 0.21147(17) 0.0228(4) Uani 1 1 d . . . . .
C15 C 0.28238(19) 0.33374(19) 0.82033(16) 0.0245(4) Uani 1 1 d . . . . .
H15A H 0.345310 0.304999 0.886447 0.029 Uiso 1 1 calc R U . . .
H15B H 0.190306 0.324289 0.840333 0.029 Uiso 1 1 calc R U . . .
C16 C 0.3167(2) 0.4795(2) 0.81029(19) 0.0323(5) Uani 1 1 d . . . . .
H16A H 0.413383 0.491048 0.803591 0.039 Uiso 1 1 calc R U . . .
H16B H 0.302483 0.531911 0.884293 0.039 Uiso 1 1 calc R U . . .
C17 C 0.2340(2) 0.5354(2) 0.7047(2) 0.0364(5) Uani 1 1 d . . . . .
H17A H 0.220528 0.629443 0.727342 0.044 Uiso 1 1 calc R U . . .
H17B H 0.144246 0.487565 0.686722 0.044 Uiso 1 1 calc R U . . .
C18 C 0.3008(2) 0.5242(2) 0.59219(19) 0.0335(5) Uani 1 1 d . . . . .
H18A H 0.358732 0.605656 0.593431 0.040 Uiso 1 1 calc R U . . .
H18B H 0.360278 0.449674 0.595989 0.040 Uiso 1 1 calc R U . . .
C19 C 0.2068(2) 0.5039(2) 0.4739(2) 0.0339(5) Uani 1 1 d . . . . .
H19A H 0.166696 0.588315 0.457533 0.041 Uiso 1 1 calc R U . . .
H19B H 0.132537 0.438648 0.479167 0.041 Uiso 1 1 calc R U . . .
C20 C 0.2797(2) 0.45539(19) 0.37088(19) 0.0305(5) Uani 1 1 d . . . . .
H20A H 0.337718 0.529591 0.353103 0.037 Uiso 1 1 calc R U . . .
H20B H 0.339081 0.385488 0.396510 0.037 Uiso 1 1 calc R U . . .
C21 C 0.1867(2) 0.4013(2) 0.2579(2) 0.0324(5) Uani 1 1 d . . . . .
H21A H 0.132843 0.473469 0.228647 0.039 Uiso 1 1 calc R U . . .
H21B H 0.123443 0.332421 0.277256 0.039 Uiso 1 1 calc R U . . .
C22 C 0.2579(2) 0.3424(2) 0.15847(19) 0.0348(5) Uani 1 1 d . . . . .
H22A H 0.188012 0.301282 0.093567 0.042 Uiso 1 1 calc R U . . .
H22B H 0.304236 0.416104 0.127287 0.042 Uiso 1 1 calc R U . . .
C23 C 0.3605(2) 0.2404(2) 0.18687(17) 0.0272(4) Uani 1 1 d . . . . .
H23A H 0.430295 0.281332 0.251970 0.033 Uiso 1 1 calc R U . . .
H23B H 0.405271 0.221270 0.116408 0.033 Uiso 1 1 calc R U . . .
C24 C 0.30989(19) 0.10811(18) 0.22267(16) 0.0210(4) Uani 1 1 d . . . . .
H24A H 0.222816 0.079128 0.172298 0.025 Uiso 1 1 calc R U . . .
H24B H 0.374913 0.041063 0.207090 0.025 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
Br1 C10 1.8703(19) . ?
Br2 C14 1.8715(19) . ?
S1 C10 1.7174(19) . ?
S1 C7 1.7439(18) . ?
S2 C14 1.7129(19) . ?
S2 C11 1.7395(18) . ?
O1 C1 1.222(2) . ?
O2 C4 1.223(2) . ?
N1 C2 1.399(2) . ?
N1 C1 1.422(2) . ?
N1 C15 1.467(2) . ?
N2 C5 1.396(2) . ?
N2 C4 1.419(2) . ?
N2 C24 1.471(2) . ?
C1 C6 1.450(2) . ?
C2 C3 1.385(3) . ?
C2 C7 1.435(3) . ?
C3 C6 1.412(3) . ?
C3 C4 1.447(2) . ?
C5 C6 1.393(3) . ?
C5 C11 1.438(3) . ?
C7 C8 1.379(3) . ?
C8 C9 1.408(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.354(3) . ?
C9 H9A 0.9500 . ?
C11 C12 1.376(2) . ?
C12 C13 1.407(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.357(3) . ?
C13 H13A 0.9500 . ?
C15 C16 1.530(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.537(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.538(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.524(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.535(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.519(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.524(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.524(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.535(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

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
C10 S1 C7 90.96(9) . . ?
C14 S2 C11 90.83(9) . . ?
C2 N1 C1 110.93(14) . . ?
C2 N1 C15 127.46(15) . . ?
C1 N1 C15 119.32(15) . . ?
C5 N2 C4 111.29(14) . . ?
C5 N2 C24 130.24(15) . . ?
C4 N2 C24 117.30(14) . . ?
O1 C1 N1 122.46(16) . . ?
O1 C1 C6 132.91(17) . . ?
N1 C1 C6 104.57(14) . . ?
C3 C2 N1 106.93(15) . . ?
C3 C2 C7 126.84(16) . . ?
N1 C2 C7 126.23(16) . . ?
C2 C3 C6 109.85(15) . . ?
C2 C3 C4 141.95(17) . . ?
C6 C3 C4 107.75(16) . . ?
O2 C4 N2 122.12(16) . . ?
O2 C4 C3 133.25(17) . . ?
N2 C4 C3 104.56(14) . . ?
C6 C5 N2 106.58(15) . . ?
C6 C5 C11 126.57(16) . . ?
N2 C5 C11 126.83(16) . . ?
C5 C6 C3 109.70(15) . . ?
C5 C6 C1 142.20(17) . . ?
C3 C6 C1 107.68(16) . . ?
C8 C7 C2 124.07(17) . . ?
C8 C7 S1 109.94(14) . . ?
C2 C7 S1 125.99(13) . . ?
C7 C8 C9 114.19(17) . . ?
C7 C8 H8A 122.9 . . ?
C9 C8 H8A 122.9 . . ?
C10 C9 C8 111.46(17) . . ?
C10 C9 H9A 124.3 . . ?
C8 C9 H9A 124.3 . . ?
C9 C10 S1 113.44(15) . . ?
C9 C10 Br1 126.35(15) . . ?
S1 C10 Br1 120.19(11) . . ?
C12 C11 C5 123.58(16) . . ?
C12 C11 S2 110.29(14) . . ?
C5 C11 S2 126.13(13) . . ?
C11 C12 C13 114.04(17) . . ?
C11 C12 H12A 123.0 . . ?
C13 C12 H12A 123.0 . . ?
C14 C13 C12 111.21(17) . . ?
C14 C13 H13A 124.4 . . ?
C12 C13 H13A 124.4 . . ?
C13 C14 S2 113.62(14) . . ?
C13 C14 Br2 126.34(15) . . ?
S2 C14 Br2 120.04(11) . . ?
N1 C15 C16 114.06(16) . . ?
N1 C15 H15A 108.7 . . ?
C16 C15 H15A 108.7 . . ?
N1 C15 H15B 108.7 . . ?
C16 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 C17 114.62(18) . . ?
C15 C16 H16A 108.6 . . ?
C17 C16 H16A 108.6 . . ?
C15 C16 H16B 108.6 . . ?
C17 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 C18 113.39(18) . . ?
C16 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C17 116.71(19) . . ?
C19 C18 H18A 108.1 . . ?
C17 C18 H18A 108.1 . . ?
C19 C18 H18B 108.1 . . ?
C17 C18 H18B 108.1 . . ?
H18A C18 H18B 107.3 . . ?
C18 C19 C20 112.32(18) . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
C21 C20 C19 114.41(18) . . ?
C21 C20 H20A 108.7 . . ?
C19 C20 H20A 108.7 . . ?
C21 C20 H20B 108.7 . . ?
C19 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C20 C21 C22 114.81(18) . . ?
C20 C21 H21A 108.6 . . ?
C22 C21 H21A 108.6 . . ?
C20 C21 H21B 108.6 . . ?
C22 C21 H21B 108.6 . . ?
H21A C21 H21B 107.5 . . ?
C23 C22 C21 118.24(17) . . ?
C23 C22 H22A 107.7 . . ?
C21 C22 H22A 107.7 . . ?
C23 C22 H22B 107.7 . . ?
C21 C22 H22B 107.7 . . ?
H22A C22 H22B 107.1 . . ?
C22 C23 C24 118.04(17) . . ?
C22 C23 H23A 107.8 . . ?
C24 C23 H23A 107.8 . . ?
C22 C23 H23B 107.8 . . ?
C24 C23 H23B 107.8 . . ?
H23A C23 H23B 107.1 . . ?
N2 C24 C23 113.64(15) . . ?
N2 C24 H24A 108.8 . . ?
C23 C24 H24A 108.8 . . ?
N2 C24 H24B 108.8 . . ?
C23 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?

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
C2 N1 C1 O1 -179.59(16) . . . . ?
C15 N1 C1 O1 -15.5(3) . . . . ?
C2 N1 C1 C6 -2.01(18) . . . . ?
C15 N1 C1 C6 162.07(15) . . . . ?
C1 N1 C2 C3 2.02(19) . . . . ?
C15 N1 C2 C3 -160.44(17) . . . . ?
C1 N1 C2 C7 -176.83(16) . . . . ?
C15 N1 C2 C7 20.7(3) . . . . ?
N1 C2 C3 C6 -1.18(19) . . . . ?
C7 C2 C3 C6 177.66(16) . . . . ?
N1 C2 C3 C4 169.6(2) . . . . ?
C7 C2 C3 C4 -11.5(4) . . . . ?
C5 N2 C4 O2 179.35(16) . . . . ?
C24 N2 C4 O2 -11.8(2) . . . . ?
C5 N2 C4 C3 -3.23(18) . . . . ?
C24 N2 C4 C3 165.66(14) . . . . ?
C2 C3 C4 O2 7.9(4) . . . . ?
C6 C3 C4 O2 178.79(19) . . . . ?
C2 C3 C4 N2 -169.1(2) . . . . ?
C6 C3 C4 N2 1.79(18) . . . . ?
C4 N2 C5 C6 3.41(18) . . . . ?
C24 N2 C5 C6 -163.62(16) . . . . ?
C4 N2 C5 C11 -174.95(16) . . . . ?
C24 N2 C5 C11 18.0(3) . . . . ?
N2 C5 C6 C3 -2.17(19) . . . . ?
C11 C5 C6 C3 176.20(16) . . . . ?
N2 C5 C6 C1 169.0(2) . . . . ?
C11 C5 C6 C1 -12.7(3) . . . . ?
C2 C3 C6 C5 174.27(14) . . . . ?
C4 C3 C6 C5 0.21(19) . . . . ?
C2 C3 C6 C1 -0.1(2) . . . . ?
C4 C3 C6 C1 -174.11(14) . . . . ?
O1 C1 C6 C5 7.2(4) . . . . ?
N1 C1 C6 C5 -170.0(2) . . . . ?
O1 C1 C6 C3 178.44(19) . . . . ?
N1 C1 C6 C3 1.23(18) . . . . ?
C3 C2 C7 C8 4.2(3) . . . . ?
N1 C2 C7 C8 -177.21(17) . . . . ?
C3 C2 C7 S1 -175.77(14) . . . . ?
N1 C2 C7 S1 2.9(3) . . . . ?
C10 S1 C7 C8 0.51(14) . . . . ?
C10 S1 C7 C2 -179.55(16) . . . . ?
C2 C7 C8 C9 179.48(16) . . . . ?
S1 C7 C8 C9 -0.6(2) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C8 C9 C10 S1 0.1(2) . . . . ?
C8 C9 C10 Br1 -178.48(13) . . . . ?
C7 S1 C10 C9 -0.34(15) . . . . ?
C7 S1 C10 Br1 178.31(11) . . . . ?
C6 C5 C11 C12 4.6(3) . . . . ?
N2 C5 C11 C12 -177.36(17) . . . . ?
C6 C5 C11 S2 -174.45(14) . . . . ?
N2 C5 C11 S2 3.6(3) . . . . ?
C14 S2 C11 C12 0.83(14) . . . . ?
C14 S2 C11 C5 179.98(16) . . . . ?
C5 C11 C12 C13 179.84(16) . . . . ?
S2 C11 C12 C13 -1.0(2) . . . . ?
C11 C12 C13 C14 0.6(2) . . . . ?
C12 C13 C14 S2 0.0(2) . . . . ?
C12 C13 C14 Br2 -179.41(13) . . . . ?
C11 S2 C14 C13 -0.50(15) . . . . ?
C11 S2 C14 Br2 178.98(11) . . . . ?
C2 N1 C15 C16 67.4(2) . . . . ?
C1 N1 C15 C16 -93.8(2) . . . . ?
N1 C15 C16 C17 53.9(2) . . . . ?
C15 C16 C17 C18 -91.3(2) . . . . ?
C16 C17 C18 C19 147.72(19) . . . . ?
C17 C18 C19 C20 -163.75(17) . . . . ?
C18 C19 C20 C21 165.54(17) . . . . ?
C19 C20 C21 C22 -175.17(17) . . . . ?
C20 C21 C22 C23 51.1(3) . . . . ?
C21 C22 C23 C24 64.9(3) . . . . ?
C5 N2 C24 C23 97.9(2) . . . . ?
C4 N2 C24 C23 -68.5(2) . . . . ?
C22 C23 C24 N2 -81.1(2) . . . . ?

