# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_B14502
_database_code_depnum_ccdc_archive 'CCDC 2194328'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2022-08-02 deposited with the CCDC.	2022-11-08 downloaded from the CCDC.
;
_audit_creation_date             2022-08-02
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
'(3,6-diphenylthieno[3,4-b]thiophene-2,4-diyl)bis(phenylmethanone)'
;
_chemical_formula_moiety         'C32 H20 O2 S2'
_chemical_formula_sum            'C32 H20 O2 S2'
_chemical_formula_weight         500.60
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C32 H20 O2 S2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.0865(6)
_cell_length_b                   12.4636(6)
_cell_length_c                   17.3007(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.435(5)
_cell_angle_gamma                90
_cell_volume                     2523.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9144
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0020
_cell_measurement_theta_min      2.4970
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.932
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.406
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_description       'diamond-like tab'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1040
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -5 -5 0.1094
0 1 -1 0.1019
-1 0 0 0.0255
1 0 0 0.0115
0 -1 1 0.1019
-1 5 5 0.1094

_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9901 -4.9972 -4.9953 -0.0509 0.0022 -0.3468
0.0015 1.0007 -0.9978 -0.0623 0.0113 0.0319
-0.9984 -0.0001 0.0012 -0.0186 -0.0574 0.0037
0.9984 0.0001 -0.0012 0.0186 0.0574 -0.0037
-0.0015 -1.0007 0.9978 0.0623 -0.0113 -0.0319
-0.9901 4.9972 4.9953 0.0509 -0.0022 0.3468

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            34392
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         2.387
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  55.00   0.50   17.50    --    1.00  37.00  53.00  118
  2  ω      3.00  28.00   0.50   17.50    --   -1.30  37.00  53.00   50
  3  ω     47.00  73.00   0.50   17.50    --    1.00  38.00   0.00   52
  4  ω    -28.00  72.00   0.50   17.50    --    1.00  57.00 -90.00  200
  5  ω     32.00  86.00   0.50   17.50    --    1.00  57.00-180.00  108
  6  ω    -28.00  31.00   0.50   17.50    --    1.00  57.00   0.00  118
  7  ω    -33.00  20.00   0.50   17.50    --   -1.30  38.00-180.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0187004000
_diffrn_orient_matrix_UB_12      -0.0242243000
_diffrn_orient_matrix_UB_13      0.0381337000
_diffrn_orient_matrix_UB_21      0.0575208000
_diffrn_orient_matrix_UB_22      0.0110770000
_diffrn_orient_matrix_UB_23      -0.0001181000
_diffrn_orient_matrix_UB_31      -0.0036651000
_diffrn_orient_matrix_UB_32      0.0502792000
_diffrn_orient_matrix_UB_33      0.0184015000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4286
_reflns_number_total             5513
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5513
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.014
_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)+(0.0489P)²+0.9654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1166
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C9(H9), C26(H26), C28(H28), C19(H19), C25(H25), C29(H29), C16(H16),
 C32(H32), C22(H22), C24(H24), C30(H30), C17(H17), C18(H18), C10(H10), C23(H23),
  C13(H13), C31(H31), C12(H12), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
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 0.45194(4) 0.33043(4) 0.45203(3) 0.05577(15) Uani 1 1 d . . . . .
S2 S 0.21967(5) 0.37882(4) 0.59641(3) 0.05897(15) Uani 1 1 d . . . . .
O1 O 0.70541(16) 0.37670(13) 0.45728(11) 0.0879(6) Uani 1 1 d . . . . .
O2 O 0.30171(17) 0.37711(16) 0.76610(10) 0.0943(6) Uani 1 1 d . . . . .
C4 C 0.36637(16) 0.35074(14) 0.51828(10) 0.0483(4) Uani 1 1 d . . . . .
C3 C 0.43258(16) 0.36810(13) 0.59795(10) 0.0470(4) Uani 1 1 d . . . . .
C14 C 0.64702(16) 0.36356(14) 0.67738(11) 0.0484(4) Uani 1 1 d . . . . .
C2 C 0.55421(16) 0.35667(13) 0.60436(10) 0.0471(4) Uani 1 1 d . . . . .
C27 C 0.15984(17) 0.34345(15) 0.43205(12) 0.0538(4) Uani 1 1 d . . . . .
C1 C 0.57343(16) 0.33709(14) 0.53103(11) 0.0501(4) Uani 1 1 d . . . . .
C8 C 0.76027(16) 0.23087(17) 0.54469(11) 0.0553(5) Uani 1 1 d . . . . .
C5 C 0.25005(17) 0.35535(15) 0.50614(11) 0.0514(4) Uani 1 1 d . . . . .
C21 C 0.46973(18) 0.47692(15) 0.78087(11) 0.0553(5) Uani 1 1 d . . . . .
C6 C 0.36066(17) 0.38829(14) 0.64862(11) 0.0527(4) Uani 1 1 d . . . . .
C7 C 0.68442(17) 0.32050(15) 0.50893(12) 0.0547(5) Uani 1 1 d . . . . .
C15 C 0.64470(17) 0.30376(17) 0.74474(12) 0.0577(5) Uani 1 1 d . . . . .
H15 H 0.583504 0.258124 0.743817 0.069 Uiso 1 1 calc R U . . .
C20 C 0.37496(19) 0.41074(16) 0.73462(12) 0.0607(5) Uani 1 1 d . . . . .
C9 C 0.72276(18) 0.14710(17) 0.58424(12) 0.0592(5) Uani 1 1 d . . . . .
H9 H 0.650580 0.150534 0.594006 0.071 Uiso 1 1 calc R U . . .
C26 C 0.52738(19) 0.55024(15) 0.74515(12) 0.0580(5) Uani 1 1 d . . . . .
H26 H 0.507426 0.558235 0.689963 0.070 Uiso 1 1 calc R U . . .
C28 C 0.17521(18) 0.27773(18) 0.37111(13) 0.0641(5) Uani 1 1 d . . . . .
H28 H 0.243368 0.240206 0.377281 0.077 Uiso 1 1 calc R U . . .
C19 C 0.74070(18) 0.42945(17) 0.68032(13) 0.0617(5) Uani 1 1 d . . . . .
H19 H 0.744707 0.469041 0.635532 0.074 Uiso 1 1 calc R U . . .
C25 C 0.6141(2) 0.61131(17) 0.79104(16) 0.0725(6) Uani 1 1 d . . . . .
H25 H 0.652841 0.660173 0.766754 0.087 Uiso 1 1 calc R U . . .
C29 C 0.0909(2) 0.2672(2) 0.30146(14) 0.0762(6) Uani 1 1 d . . . . .
H29 H 0.102830 0.222992 0.260976 0.091 Uiso 1 1 calc R U . . .
C16 C 0.7319(2) 0.3115(2) 0.81259(13) 0.0740(6) Uani 1 1 d . . . . .
H16 H 0.729939 0.270632 0.857214 0.089 Uiso 1 1 calc R U . . .
C32 C 0.0574(2) 0.3988(2) 0.41987(15) 0.0750(6) Uani 1 1 d . . . . .
H32 H 0.045404 0.444618 0.459411 0.090 Uiso 1 1 calc R U . . .
C22 C 0.4992(2) 0.46738(19) 0.86387(13) 0.0718(6) Uani 1 1 d . . . . .
H22 H 0.460320 0.419234 0.888610 0.086 Uiso 1 1 calc R U . . .
C24 C 0.6435(2) 0.6003(2) 0.87246(17) 0.0811(7) Uani 1 1 d . . . . .
H24 H 0.702764 0.641206 0.903163 0.097 Uiso 1 1 calc R U . . .
C30 C -0.0099(2) 0.3209(2) 0.29136(16) 0.0819(7) Uani 1 1 d . . . . .
H30 H -0.067100 0.312564 0.244568 0.098 Uiso 1 1 calc R U . . .
C17 C 0.8220(2) 0.3792(2) 0.81479(16) 0.0834(7) Uani 1 1 d . . . . .
H17 H 0.879685 0.386034 0.861463 0.100 Uiso 1 1 calc R U . . .
C18 C 0.8272(2) 0.4367(2) 0.74839(16) 0.0793(7) Uani 1 1 d . . . . .
H18 H 0.889581 0.480896 0.749530 0.095 Uiso 1 1 calc R U . . .
C10 C 0.7908(2) 0.0587(2) 0.60934(14) 0.0813(7) Uani 1 1 d . . . . .
H10 H 0.764192 0.002568 0.635205 0.098 Uiso 1 1 calc R U . . .
C23 C 0.5857(2) 0.5290(2) 0.90903(15) 0.0838(7) Uani 1 1 d . . . . .
H23 H 0.605216 0.522614 0.964332 0.101 Uiso 1 1 calc R U . . .
C13 C 0.8697(2) 0.2256(3) 0.53230(15) 0.0859(8) Uani 1 1 d . . . . .
H13 H 0.897091 0.281291 0.506473 0.103 Uiso 1 1 calc R U . . .
C31 C -0.0263(2) 0.3872(2) 0.35061(18) 0.0895(8) Uani 1 1 d . . . . .
H31 H -0.094697 0.424503 0.343802 0.107 Uiso 1 1 calc R U . . .
C12 C 0.9374(2) 0.1368(4) 0.5587(2) 0.1131(12) Uani 1 1 d . . . . .
H12 H 1.010770 0.133322 0.551050 0.136 Uiso 1 1 calc R U . . .
C11 C 0.8971(3) 0.0539(3) 0.59615(18) 0.1086(11) Uani 1 1 d . . . . .
H11 H 0.942680 -0.006089 0.612610 0.130 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 C4 1.7431(17) . ?
S1 C1 1.741(2) . ?
S2 C5 1.7163(18) . ?
S2 C6 1.722(2) . ?
O1 C7 1.211(2) . ?
O2 C20 1.223(2) . ?
C4 C3 1.427(3) . ?
C4 C5 1.370(3) . ?
C3 C2 1.453(3) . ?
C3 C6 1.403(2) . ?
C14 C2 1.468(3) . ?
C14 C15 1.390(3) . ?
C14 C19 1.389(3) . ?
C2 C1 1.367(2) . ?
C27 C5 1.469(3) . ?
C27 C28 1.384(3) . ?
C27 C32 1.386(3) . ?
C1 C7 1.498(3) . ?
C8 C7 1.479(3) . ?
C8 C9 1.385(3) . ?
C8 C13 1.393(3) . ?
C21 C20 1.475(3) . ?
C21 C26 1.385(3) . ?
C21 C22 1.396(3) . ?
C6 C20 1.481(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.372(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(3) . ?
C26 H26 0.9300 . ?
C26 C25 1.376(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.377(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.369(3) . ?
C25 H25 0.9300 . ?
C25 C24 1.371(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.363(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.370(3) . ?
C32 H32 0.9300 . ?
C32 C31 1.370(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.373(4) . ?
C24 H24 0.9300 . ?
C24 C23 1.378(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.369(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.369(4) . ?
C18 H18 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.360(4) . ?
C23 H23 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.384(4) . ?
C31 H31 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.372(5) . ?
C11 H11 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C4 89.97(9) . . ?
C5 S2 C6 94.63(9) . . ?
C3 C4 S1 112.04(14) . . ?
C5 C4 S1 131.28(15) . . ?
C5 C4 C3 116.66(16) . . ?
C4 C3 C2 111.83(15) . . ?
C6 C3 C4 110.19(17) . . ?
C6 C3 C2 137.95(18) . . ?
C15 C14 C2 121.30(16) . . ?
C19 C14 C2 120.46(17) . . ?
C19 C14 C15 118.23(19) . . ?
C3 C2 C14 126.96(15) . . ?
C1 C2 C3 110.44(17) . . ?
C1 C2 C14 122.60(17) . . ?
C28 C27 C5 120.88(18) . . ?
C28 C27 C32 117.6(2) . . ?
C32 C27 C5 121.52(19) . . ?
C2 C1 S1 115.58(15) . . ?
C2 C1 C7 129.15(18) . . ?
C7 C1 S1 115.26(13) . . ?
C9 C8 C7 122.05(17) . . ?
C9 C8 C13 118.7(2) . . ?
C13 C8 C7 119.0(2) . . ?
C4 C5 S2 108.17(14) . . ?
C4 C5 C27 129.78(16) . . ?
C27 C5 S2 122.05(14) . . ?
C26 C21 C20 122.42(18) . . ?
C26 C21 C22 119.2(2) . . ?
C22 C21 C20 118.37(18) . . ?
C3 C6 S2 110.26(14) . . ?
C3 C6 C20 136.6(2) . . ?
C20 C6 S2 113.09(14) . . ?
O1 C7 C1 118.30(19) . . ?
O1 C7 C8 121.56(18) . . ?
C8 C7 C1 119.90(16) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.54(19) . . ?
C16 C15 H15 119.7 . . ?
O2 C20 C21 120.02(18) . . ?
O2 C20 C6 117.8(2) . . ?
C21 C20 C6 122.07(16) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(2) . . ?
C10 C9 H9 119.5 . . ?
C21 C26 H26 119.9 . . ?
C25 C26 C21 120.2(2) . . ?
C25 C26 H26 119.9 . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.8(2) . . ?
C29 C28 H28 119.6 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.7(2) . . ?
C18 C19 H19 119.6 . . ?
C26 C25 H25 119.9 . . ?
C24 C25 C26 120.2(2) . . ?
C24 C25 H25 119.9 . . ?
C28 C29 H29 119.7 . . ?
C30 C29 C28 120.6(2) . . ?
C30 C29 H29 119.7 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C27 C32 H32 119.4 . . ?
C31 C32 C27 121.2(2) . . ?
C31 C32 H32 119.4 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.1(2) . . ?
C23 C22 H22 120.0 . . ?
C25 C24 H24 119.8 . . ?
C25 C24 C23 120.3(2) . . ?
C23 C24 H24 119.8 . . ?
C29 C30 H30 120.3 . . ?
C29 C30 C31 119.5(2) . . ?
C31 C30 H30 120.3 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.8(3) . . ?
C11 C10 H10 120.1 . . ?
C22 C23 C24 120.0(2) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C8 C13 H13 120.2 . . ?
C12 C13 C8 119.5(3) . . ?
C12 C13 H13 120.2 . . ?
C32 C31 H31 119.8 . . ?
C30 C31 C32 120.4(2) . . ?
C30 C31 H31 119.8 . . ?
C13 C12 H12 119.7 . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 H12 119.7 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C4 C3 C2 -4.15(19) . . . . ?
S1 C4 C3 C6 177.65(12) . . . . ?
S1 C4 C5 S2 -179.46(12) . . . . ?
S1 C4 C5 C27 0.6(3) . . . . ?
S1 C1 C7 O1 54.4(2) . . . . ?
S1 C1 C7 C8 -120.10(17) . . . . ?
S2 C6 C20 O2 30.1(3) . . . . ?
S2 C6 C20 C21 -146.18(17) . . . . ?
C4 S1 C1 C2 -1.74(15) . . . . ?
C4 S1 C1 C7 178.26(14) . . . . ?
C4 C3 C2 C14 -176.75(16) . . . . ?
C4 C3 C2 C1 2.8(2) . . . . ?
C4 C3 C6 S2 2.57(19) . . . . ?
C4 C3 C6 C20 179.4(2) . . . . ?
C3 C4 C5 S2 -1.5(2) . . . . ?
C3 C4 C5 C27 178.58(17) . . . . ?
C3 C2 C1 S1 -0.3(2) . . . . ?
C3 C2 C1 C7 179.69(17) . . . . ?
C3 C6 C20 O2 -146.7(2) . . . . ?
C3 C6 C20 C21 37.1(3) . . . . ?
C14 C2 C1 S1 179.29(13) . . . . ?
C14 C2 C1 C7 -0.7(3) . . . . ?
C14 C15 C16 C17 0.6(4) . . . . ?
C14 C19 C18 C17 -0.3(4) . . . . ?
C2 C3 C6 S2 -174.93(18) . . . . ?
C2 C3 C6 C20 1.9(4) . . . . ?
C2 C14 C15 C16 -179.75(19) . . . . ?
C2 C14 C19 C18 179.6(2) . . . . ?
C2 C1 C7 O1 -125.6(2) . . . . ?
C2 C1 C7 C8 59.9(3) . . . . ?
C27 C28 C29 C30 -0.4(4) . . . . ?
C27 C32 C31 C30 -0.6(4) . . . . ?
C1 S1 C4 C3 3.32(14) . . . . ?
C1 S1 C4 C5 -178.61(19) . . . . ?
C8 C9 C10 C11 0.9(4) . . . . ?
C8 C13 C12 C11 0.7(5) . . . . ?
C5 S2 C6 C3 -2.99(14) . . . . ?
C5 S2 C6 C20 179.38(14) . . . . ?
C5 C4 C3 C2 177.47(15) . . . . ?
C5 C4 C3 C6 -0.7(2) . . . . ?
C5 C27 C28 C29 -179.6(2) . . . . ?
C5 C27 C32 C31 -179.9(2) . . . . ?
C21 C26 C25 C24 -0.4(3) . . . . ?
C21 C22 C23 C24 -0.1(4) . . . . ?
C6 S2 C5 C4 2.51(15) . . . . ?
C6 S2 C5 C27 -177.52(16) . . . . ?
C6 C3 C2 C14 0.7(3) . . . . ?
C6 C3 C2 C1 -179.7(2) . . . . ?
C7 C8 C9 C10 172.8(2) . . . . ?
C7 C8 C13 C12 -173.7(2) . . . . ?
C15 C14 C2 C3 51.3(3) . . . . ?
C15 C14 C2 C1 -128.3(2) . . . . ?
C15 C14 C19 C18 -1.3(3) . . . . ?
C15 C16 C17 C18 -2.2(4) . . . . ?
C20 C21 C26 C25 178.99(19) . . . . ?
C20 C21 C22 C23 -178.9(2) . . . . ?
C9 C8 C7 O1 -159.7(2) . . . . ?
C9 C8 C7 C1 14.6(3) . . . . ?
C9 C8 C13 C12 0.8(4) . . . . ?
C9 C10 C11 C12 0.6(4) . . . . ?
C26 C21 C20 O2 -154.0(2) . . . . ?
C26 C21 C20 C6 22.1(3) . . . . ?
C26 C21 C22 C23 -1.0(3) . . . . ?
C26 C25 C24 C23 -0.7(4) . . . . ?
C28 C27 C5 S2 -148.72(17) . . . . ?
C28 C27 C5 C4 31.2(3) . . . . ?
C28 C27 C32 C31 1.2(4) . . . . ?
C28 C29 C30 C31 1.1(4) . . . . ?
C19 C14 C2 C3 -129.7(2) . . . . ?
C19 C14 C2 C1 50.8(3) . . . . ?
C19 C14 C15 C16 1.2(3) . . . . ?
C25 C24 C23 C22 0.9(4) . . . . ?
C29 C30 C31 C32 -0.6(4) . . . . ?
C16 C17 C18 C19 2.0(4) . . . . ?
C32 C27 C5 S2 32.5(3) . . . . ?
C32 C27 C5 C4 -147.6(2) . . . . ?
C32 C27 C28 C29 -0.7(3) . . . . ?
C22 C21 C20 O2 23.7(3) . . . . ?
C22 C21 C20 C6 -160.1(2) . . . . ?
C22 C21 C26 C25 1.2(3) . . . . ?
C13 C8 C7 O1 14.6(3) . . . . ?
C13 C8 C7 C1 -171.1(2) . . . . ?
C13 C8 C9 C10 -1.6(3) . . . . ?
C13 C12 C11 C10 -1.4(5) . . . . ?

_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 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.635

####################################################################### 
# 
# 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_B14226P1
_database_code_depnum_ccdc_archive 'CCDC 2194330'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2022-08-02 deposited with the CCDC.	2022-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
;
'dimethyl 4,4'-(2,4-bis(4-(methoxycarbonyl)benzoyl)thieno[3,4-b]
 thiophene-3,6-diyl)dibenzoate'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H28 O10 S2'
_chemical_formula_sum            'C40 H28 O10 S2'
_chemical_formula_weight         732.74

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'
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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.7293(14)
_cell_length_b                   14.6779(4)
_cell_length_c                   11.7861(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.661(7)
_cell_angle_gamma                90
_cell_volume                     3401.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10125
_cell_measurement_theta_min      6.8
_cell_measurement_theta_max      66.6

_exptl_crystal_description       'elongated platelet'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    1.951
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_process_details   'Abscor (Higashi-Rigaku,1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  'Confocal CMF Osmic'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'RX Rapid2 curved IP'
_diffrn_measurement_device       
;
Crystal Goniometer chi-partial
;
_diffrn_measurement_device_type  
;
Rigaku RAXIS conversion
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            27560
_diffrn_reflns_av_unetI/netI     0.0959
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         6.755
_diffrn_reflns_theta_max         63.018
_diffrn_reflns_theta_full        63.018
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             5427
_reflns_number_gt                2556
_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.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0991P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5422
_refine_ls_number_parameters     473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1313
_refine_ls_R_factor_gt           0.0674
_refine_ls_wR_factor_ref         0.2094
_refine_ls_wR_factor_gt          0.1479
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
S2 S 0.58872(6) 0.55594(9) 0.84515(9) 0.0636(4) Uani 1 1 d . . . . .
S1 S 0.52161(6) 0.37875(9) 0.57296(10) 0.0655(4) Uani 1 1 d . . . . .
O10 O 0.87346(15) 0.4161(2) 0.4872(3) 0.0719(10) Uani 1 1 d . . . . .
O6 O 0.48505(16) 0.6242(2) 0.9925(3) 0.0795(11) Uani 1 1 d . . . . .
O4 O 0.16364(15) 0.4361(2) 0.9970(3) 0.0796(11) Uani 1 1 d . . . . .
O5 O 0.11376(16) 0.4523(2) 0.8214(3) 0.0846(11) Uani 1 1 d . . . . .
O1 O 0.41090(16) 0.3133(3) 0.4258(3) 0.0871(12) Uani 1 1 d . . . . .
O8 O 0.19895(17) 0.7845(2) 0.6232(3) 0.0805(11) Uani 1 1 d . . . . .
O3 O 0.10379(17) 0.2202(3) 0.7004(3) 0.0915(12) Uani 1 1 d . . . . .
O9 O 0.92583(17) 0.4755(3) 0.6463(3) 0.0961(13) Uani 1 1 d . . . . .
O7 O 0.15124(19) 0.7328(3) 0.7761(3) 0.0909(12) Uani 1 1 d . . . . .
O2 O 0.06589(19) 0.2685(3) 0.5262(3) 0.1015(14) Uani 1 1 d . . . . .
C16 C 0.3569(2) 0.4454(3) 0.7436(3) 0.0492(12) Uani 1 1 d . . . . .
C19 C 0.2325(2) 0.4446(3) 0.8410(4) 0.0525(12) Uani 1 1 d . . . . .
C8 C 0.3200(2) 0.3092(3) 0.5428(4) 0.0545(12) Uani 1 1 d . . . . .
C3 C 0.4849(2) 0.4821(3) 0.7388(3) 0.0531(13) Uani 1 1 d . . . . .
C21 C 0.2994(2) 0.4802(3) 0.6848(3) 0.0542(12) Uani 1 1 d . . . . .
H21 H 0.302441 0.504551 0.612511 0.065 Uiso 1 1 calc R U . . .
C9 C 0.3050(2) 0.2665(3) 0.6429(4) 0.0590(13) Uani 1 1 d . . . . .
H9 H 0.339807 0.250857 0.697387 0.071 Uiso 1 1 calc R U . . .
C36 C 0.8059(2) 0.4498(3) 0.6345(4) 0.0549(13) Uani 1 1 d . . . . .
C18 C 0.2913(2) 0.4113(3) 0.9011(4) 0.0566(13) Uani 1 1 d . . . . .
H18 H 0.288609 0.388383 0.974194 0.068 Uiso 1 1 calc R U . . .
C33 C 0.6743(2) 0.4673(3) 0.7056(4) 0.0549(12) Uani 1 1 d . . . . .
C5 C 0.6051(2) 0.4825(3) 0.7360(3) 0.0517(12) Uani 1 1 d . . . . .
C20 C 0.2374(2) 0.4795(3) 0.7315(4) 0.0585(13) Uani 1 1 d . . . . .
H20 H 0.198907 0.502256 0.690118 0.070 Uiso 1 1 calc R U . . .
C17 C 0.3534(2) 0.4115(3) 0.8540(3) 0.0554(12) Uani 1 1 d . . . . .
H17 H 0.392208 0.389499 0.895205 0.067 Uiso 1 1 calc R U . . .
C35 C 0.7515(2) 0.4098(3) 0.5727(4) 0.0579(13) Uani 1 1 d . . . . .
H35 H 0.758662 0.376535 0.507571 0.069 Uiso 1 1 calc R U . . .
C6 C 0.5031(2) 0.5447(3) 0.8254(4) 0.0502(12) Uani 1 1 d . . . . .
C2 C 0.4233(2) 0.4384(3) 0.6911(3) 0.0509(12) Uani 1 1 d . . . . .
C4 C 0.5437(2) 0.4496(3) 0.6860(3) 0.0560(13) Uani 1 1 d . . . . .
C7 C 0.3906(2) 0.3334(3) 0.5183(4) 0.0603(13) Uani 1 1 d . . . . .
C34 C 0.6866(2) 0.4186(3) 0.6069(4) 0.0564(13) Uani 1 1 d . . . . .
H34 H 0.650357 0.391870 0.563745 0.068 Uiso 1 1 calc R U . . .
C22 C 0.1683(3) 0.4434(3) 0.8962(4) 0.0619(14) Uani 1 1 d . . . . .
C10 C 0.2376(3) 0.2470(3) 0.6615(4) 0.0598(13) Uani 1 1 d . . . . .
H10 H 0.227209 0.218313 0.728306 0.072 Uiso 1 1 calc R U . . .
C1 C 0.4362(2) 0.3842(3) 0.6016(4) 0.0528(12) Uani 1 1 d . . . . .
C38 C 0.7307(2) 0.5032(3) 0.7702(4) 0.0623(13) Uani 1 1 d . . . . .
H38 H 0.724446 0.533095 0.838104 0.075 Uiso 1 1 calc R U . . .
C25 C 0.3958(2) 0.6406(3) 0.8478(4) 0.0555(13) Uani 1 1 d . . . . .
C39 C 0.8754(3) 0.4482(3) 0.5936(4) 0.0639(14) Uani 1 1 d . . . . .
C11 C 0.1857(2) 0.2710(3) 0.5792(4) 0.0596(13) Uani 1 1 d . . . . .
C24 C 0.4625(2) 0.6026(3) 0.8970(4) 0.0578(13) Uani 1 1 d . . . . .
C30 C 0.3876(2) 0.6773(3) 0.7385(4) 0.0609(14) Uani 1 1 d . . . . .
H30 H 0.423707 0.677282 0.692548 0.073 Uiso 1 1 calc R U . . .
C13 C 0.2678(2) 0.3298(3) 0.4613(4) 0.0608(14) Uani 1 1 d . . . . .
H13 H 0.278192 0.356302 0.393222 0.073 Uiso 1 1 calc R U . . .
C37 C 0.7951(2) 0.4950(3) 0.7350(4) 0.0635(14) Uani 1 1 d . . . . .
H37 H 0.831757 0.519968 0.778802 0.076 Uiso 1 1 calc R U . . .
C26 C 0.3414(3) 0.6418(3) 0.9162(4) 0.0629(14) Uani 1 1 d . . . . .
H26 H 0.347070 0.619939 0.990383 0.075 Uiso 1 1 calc R U . . .
C28 C 0.2708(2) 0.7116(3) 0.7641(4) 0.0583(13) Uani 1 1 d . . . . .
C27 C 0.2794(2) 0.6752(3) 0.8739(4) 0.0621(14) Uani 1 1 d . . . . .
H27 H 0.242784 0.673661 0.918867 0.075 Uiso 1 1 calc R U . . .
C29 C 0.3256(3) 0.7137(3) 0.6987(4) 0.0635(14) Uani 1 1 d . . . . .
H29 H 0.320775 0.740046 0.626701 0.076 Uiso 1 1 calc R U . . .
C31 C 0.2011(3) 0.7436(4) 0.7242(5) 0.0690(15) Uani 1 1 d . . . . .
C12 C 0.2008(3) 0.3119(3) 0.4786(4) 0.0667(14) Uani 1 1 d . . . . .
H12 H 0.166286 0.327146 0.423448 0.080 Uiso 1 1 calc R U . . .
C14 C 0.1120(3) 0.2536(4) 0.5972(5) 0.0726(16) Uani 1 1 d . . . . .
C40 C 0.9374(2) 0.4192(4) 0.4340(4) 0.0893(18) Uani 1 1 d . . . . .
H40A H 0.931542 0.391303 0.360155 0.134 Uiso 1 1 calc R U . . .
H40B H 0.971630 0.386950 0.480451 0.134 Uiso 1 1 calc R U . . .
H40C H 0.951136 0.481500 0.426109 0.134 Uiso 1 1 calc R U . . .
C32 C 0.1334(3) 0.8201(4) 0.5773(4) 0.0979(19) Uani 1 1 d . . . . .
H32A H 0.114443 0.780450 0.518128 0.147 Uiso 1 1 calc R U . . .
H32B H 0.139403 0.879848 0.546712 0.147 Uiso 1 1 calc R U . . .
H32C H 0.103051 0.823303 0.636922 0.147 Uiso 1 1 calc R U . . .
C23 C 0.0480(2) 0.4532(4) 0.8693(4) 0.109(2) Uani 1 1 d . . . . .
H23A H 0.012647 0.462404 0.809550 0.163 Uiso 1 1 calc R U . . .
H23B H 0.047019 0.501665 0.923827 0.163 Uiso 1 1 calc R U . . .
H23C H 0.041005 0.396019 0.906242 0.163 Uiso 1 1 calc R U . . .
C15 C 0.0337(3) 0.2026(5) 0.7252(5) 0.126(3) Uani 1 1 d . . . . .
H15A H 0.013239 0.160214 0.670624 0.188 Uiso 1 1 calc R U . . .
H15B H 0.008501 0.258591 0.721160 0.188 Uiso 1 1 calc R U . . .
H15C H 0.033241 0.177325 0.800325 0.188 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
S2 C6 1.695(4) . ?
S2 C5 1.729(4) . ?
S1 C4 1.718(4) . ?
S1 C1 1.747(4) . ?
O10 C39 1.337(5) . ?
O10 C40 1.454(5) . ?
O6 C24 1.218(4) . ?
O4 C22 1.203(5) . ?
O5 C22 1.341(5) . ?
O5 C23 1.457(5) . ?
O1 C7 1.227(5) . ?
O8 C31 1.331(5) . ?
O8 C32 1.458(5) . ?
O3 C14 1.333(5) . ?
O3 C15 1.460(5) . ?
O9 C39 1.198(5) . ?
O7 C31 1.211(6) . ?
O2 C14 1.205(5) . ?
C16 C21 1.379(5) . ?
C16 C17 1.400(5) . ?
C16 C2 1.497(5) . ?
C19 C18 1.396(5) . ?
C19 C20 1.400(5) . ?
C19 C22 1.471(6) . ?
C8 C13 1.383(5) . ?
C8 C9 1.389(5) . ?
C8 C7 1.490(6) . ?
C3 C6 1.399(5) . ?
C3 C4 1.441(5) . ?
C3 C2 1.447(5) . ?
C21 C20 1.382(5) . ?
C9 C10 1.395(6) . ?
C36 C35 1.378(5) . ?
C36 C37 1.389(6) . ?
C36 C39 1.491(6) . ?
C18 C17 1.386(5) . ?
C33 C38 1.398(5) . ?
C33 C34 1.403(5) . ?
C33 C5 1.458(5) . ?
C5 C4 1.390(5) . ?
C35 C34 1.380(5) . ?
C6 C24 1.478(6) . ?
C2 C1 1.362(5) . ?
C7 C1 1.478(6) . ?
C10 C11 1.397(6) . ?
C38 C37 1.373(5) . ?
C25 C30 1.393(5) . ?
C25 C26 1.394(5) . ?
C25 C24 1.501(6) . ?
C11 C12 1.383(6) . ?
C11 C14 1.508(6) . ?
C30 C29 1.382(6) . ?
C13 C12 1.379(6) . ?
C26 C27 1.373(6) . ?
C28 C29 1.378(6) . ?
C28 C27 1.398(6) . ?
C28 C31 1.492(6) . ?

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
C6 S2 C5 94.7(2) . . ?
C4 S1 C1 90.6(2) . . ?
C39 O10 C40 115.7(4) . . ?
C22 O5 C23 116.0(4) . . ?
C31 O8 C32 117.2(4) . . ?
C14 O3 C15 115.8(4) . . ?
C21 C16 C17 119.9(4) . . ?
C21 C16 C2 121.9(4) . . ?
C17 C16 C2 118.1(4) . . ?
C18 C19 C20 118.7(4) . . ?
C18 C19 C22 118.7(4) . . ?
C20 C19 C22 122.6(4) . . ?
C13 C8 C9 119.4(5) . . ?
C13 C8 C7 117.9(4) . . ?
C9 C8 C7 122.7(4) . . ?
C6 C3 C4 111.5(4) . . ?
C6 C3 C2 137.1(4) . . ?
C4 C3 C2 111.4(4) . . ?
C16 C21 C20 121.1(4) . . ?
C8 C9 C10 119.8(4) . . ?
C35 C36 C37 119.2(4) . . ?
C35 C36 C39 121.3(4) . . ?
C37 C36 C39 119.5(4) . . ?
C17 C18 C19 121.4(4) . . ?
C38 C33 C34 117.4(4) . . ?
C38 C33 C5 121.9(4) . . ?
C34 C33 C5 120.7(4) . . ?
C4 C5 C33 130.1(4) . . ?
C4 C5 S2 108.9(3) . . ?
C33 C5 S2 120.9(3) . . ?
C21 C20 C19 119.9(4) . . ?
C18 C17 C16 119.0(4) . . ?
C36 C35 C34 120.4(4) . . ?
C3 C6 C24 132.5(4) . . ?
C3 C6 S2 110.9(3) . . ?
C24 C6 S2 116.5(3) . . ?
C1 C2 C3 110.9(4) . . ?
C1 C2 C16 125.8(4) . . ?
C3 C2 C16 123.0(4) . . ?
C5 C4 C3 113.9(4) . . ?
C5 C4 S1 134.1(4) . . ?
C3 C4 S1 111.9(3) . . ?
O1 C7 C1 119.1(4) . . ?
O1 C7 C8 119.5(4) . . ?
C1 C7 C8 121.3(4) . . ?
C35 C34 C33 121.1(4) . . ?
O4 C22 O5 122.4(5) . . ?
O4 C22 C19 125.1(5) . . ?
O5 C22 C19 112.5(4) . . ?
C9 C10 C11 119.6(4) . . ?
C2 C1 C7 131.9(4) . . ?
C2 C1 S1 114.8(3) . . ?
C7 C1 S1 113.1(3) . . ?
C37 C38 C33 121.1(5) . . ?
C30 C25 C26 119.4(4) . . ?
C30 C25 C24 122.3(4) . . ?
C26 C25 C24 118.3(4) . . ?
O9 C39 O10 124.3(5) . . ?
O9 C39 C36 125.0(5) . . ?
O10 C39 C36 110.6(4) . . ?
C12 C11 C10 120.5(5) . . ?
C12 C11 C14 118.2(5) . . ?
C10 C11 C14 121.3(5) . . ?
O6 C24 C6 120.2(4) . . ?
O6 C24 C25 120.2(4) . . ?
C6 C24 C25 119.4(4) . . ?
C29 C30 C25 119.9(5) . . ?
C12 C13 C8 121.6(4) . . ?
C38 C37 C36 120.6(4) . . ?
C27 C26 C25 120.0(5) . . ?
C29 C28 C27 119.0(5) . . ?
C29 C28 C31 124.1(5) . . ?
C27 C28 C31 116.8(5) . . ?
C26 C27 C28 120.6(5) . . ?
C28 C29 C30 120.9(5) . . ?
O7 C31 O8 122.8(5) . . ?
O7 C31 C28 124.5(5) . . ?
O8 C31 C28 112.7(5) . . ?
C13 C12 C11 119.0(4) . . ?
O2 C14 O3 124.1(5) . . ?
O2 C14 C11 123.6(5) . . ?
O3 C14 C11 112.4(5) . . ?

_refine_diff_density_max         0.363
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.068




####################################################################### 
# 
# 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_B14319F2
_database_code_depnum_ccdc_archive 'CCDC 2194331'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2022-08-03 deposited with the CCDC.	2022-11-08 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_B14319F2            
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: presence of a disordered solvent molecule of deuterated chlorofom 
is likely to be responsible of the loss of diffraction signal at room temperature
;
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
"'4,4'-(2,4-bis(4-cyanobenzoyl)thieno[3,4-b]thiophene-3,6-diyl)dibenzonitrile deuterated chloroform solvate'"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H16 N4 O2 S2, C D Cl3'
_chemical_formula_sum            'C37 H16 D1 Cl3 N4 O2 S2'
_chemical_formula_weight         721.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   11.4125(9)
_cell_length_b                   12.1675(8)
_cell_length_c                   12.9619(10)
_cell_angle_alpha                77.294(6)
_cell_angle_beta                 83.420(7)
_cell_angle_gamma                74.234(6)
_cell_volume                     1686.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4312
_cell_measurement_theta_min      3.3470
_cell_measurement_theta_max      21.9480

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_F_000             732
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.436
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.970
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 5 2 0.0374
-1 -5 -3 0.0463
2 -5 0 0.0472
5 1 5 0.0738
-1 0 -1 0.0784
-1 1 5 0.0259
0 -1 -5 0.0268
-5 -3 0 0.0797
5 3 -1 0.0775
_exptl_absorpt_correction_T_min  0.584
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            21940
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.459
_diffrn_reflns_theta_max         23.012
_diffrn_reflns_theta_full        23.012
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4707
_reflns_number_gt                3065
_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.
;

_computing_data_collection       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0539P)²+5.7455P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4706
_refine_ls_number_parameters     470
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.1254
_refine_ls_R_factor_gt           0.0753
_refine_ls_wR_factor_ref         0.2196
_refine_ls_wR_factor_gt          0.1754
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.82497(17) 0.70997(15) 0.56358(17) 0.0748(6) Uani 1 1 d . . . . .
O2 O 0.3071(4) 0.5193(4) 0.5936(4) 0.0780(14) Uani 1 1 d . . . . .
N2 N 0.9639(10) -0.0694(7) 0.6269(7) 0.133(3) Uani 1 1 d . . . . .
C2 C 0.8011(6) 0.5794(5) 0.6323(5) 0.0635(18) Uani 1 1 d . . . . .
C1 C 0.6816(6) 0.7611(5) 0.5198(5) 0.0575(17) Uani 1 1 d . . . . .
N1 N 0.5273(7) 1.2880(5) 0.1774(5) 0.090(2) Uani 1 1 d . . . . .
O1 O 0.9859(7) 0.5173(5) 0.7157(7) 0.149(3) Uani 1 1 d . . . . .
S2 S 0.46714(15) 0.67282(13) 0.54740(12) 0.0538(5) Uani 1 1 d . . . . .
N3 N 0.7734(8) 0.0295(6) 1.0759(5) 0.106(2) Uani 1 1 d . . . . .
C3 C 0.6800(6) 0.5784(5) 0.6260(4) 0.0492(15) Uani 1 1 d . . . . .
N4 N 0.3335(11) 0.1020(9) 1.1176(7) 0.178(5) Uani 1 1 d . . . . .
C4 C 0.6127(6) 0.6801(5) 0.5605(4) 0.0523(16) Uani 1 1 d . . . . .
C5 C 0.6052(6) 0.4998(4) 0.6749(4) 0.0480(14) Uani 1 1 d . . . . .
C6 C 0.4902(6) 0.5406(5) 0.6387(4) 0.0506(15) Uani 1 1 d . . . . .
C7 C 0.6449(7) 0.8757(5) 0.4471(5) 0.0598(17) Uani 1 1 d . . . . .
C8 C 0.5367(7) 0.9109(5) 0.3980(5) 0.0661(19) Uani 1 1 d . . . . .
H8 H 0.483637 0.862687 0.412377 0.079 Uiso 1 1 calc R U . . .
C9 C 0.5045(8) 1.0173(6) 0.3271(5) 0.075(2) Uani 1 1 d . . . . .
H9 H 0.430738 1.040161 0.294721 0.090 Uiso 1 1 calc R U . . .
C10 C 0.5846(7) 1.0880(5) 0.3060(5) 0.0637(18) Uani 1 1 d . . . . .
C11 C 0.6909(8) 1.0554(6) 0.3558(6) 0.077(2) Uani 1 1 d . . . . .
H11 H 0.743403 1.104158 0.342093 0.093 Uiso 1 1 calc R U . . .
C12 C 0.7216(7) 0.9503(5) 0.4269(6) 0.074(2) Uani 1 1 d . . . . .
H12 H 0.793869 0.929528 0.461321 0.088 Uiso 1 1 calc R U . . .
C13 C 0.5519(8) 1.2001(6) 0.2336(5) 0.076(2) Uani 1 1 d . . . . .
C14 C 0.9090(7) 0.4905(6) 0.6762(7) 0.080(2) Uani 1 1 d . . . . .
C15 C 0.9239(6) 0.3677(6) 0.6667(5) 0.0628(17) Uani 1 1 d . . . . .
C16 C 0.9836(6) 0.2758(6) 0.7413(6) 0.074(2) Uani 1 1 d . . . . .
H16 H 1.015238 0.290074 0.798566 0.088 Uiso 1 1 calc R U . . .
C17 C 0.9960(7) 0.1633(6) 0.7305(6) 0.080(2) Uani 1 1 d . . . . .
H17 H 1.035808 0.101758 0.781126 0.096 Uiso 1 1 calc R U . . .
C18 C 0.9504(7) 0.1404(6) 0.6463(6) 0.0705(19) Uani 1 1 d . . . . .
C19 C 0.8957(7) 0.2314(6) 0.5683(6) 0.074(2) Uani 1 1 d . . . . .
H19 H 0.868766 0.216553 0.508913 0.089 Uiso 1 1 calc R U . . .
C20 C 0.8817(6) 0.3445(6) 0.5798(6) 0.0689(19) Uani 1 1 d . . . . .
H20 H 0.843440 0.405994 0.528342 0.083 Uiso 1 1 calc R U . . .
C21 C 0.9589(9) 0.0227(8) 0.6358(7) 0.093(3) Uani 1 1 d . . . . .
C22 C 0.6491(5) 0.3945(5) 0.7578(4) 0.0474(14) Uani 1 1 d . . . . .
C23 C 0.6891(6) 0.4079(5) 0.8502(5) 0.0568(16) Uani 1 1 d . . . . .
H23 H 0.694464 0.480966 0.856846 0.068 Uiso 1 1 calc R U . . .
C24 C 0.7211(6) 0.3136(6) 0.9328(5) 0.0643(18) Uani 1 1 d . . . . .
H24 H 0.747169 0.323235 0.994811 0.077 Uiso 1 1 calc R U . . .
C25 C 0.7139(6) 0.2044(5) 0.9223(5) 0.0598(17) Uani 1 1 d . . . . .
C26 C 0.6769(6) 0.1900(5) 0.8301(5) 0.0599(17) Uani 1 1 d . . . . .
H26 H 0.673901 0.116507 0.822621 0.072 Uiso 1 1 calc R U . . .
C27 C 0.6438(6) 0.2854(5) 0.7478(5) 0.0516(15) Uani 1 1 d . . . . .
H27 H 0.618024 0.275585 0.685665 0.062 Uiso 1 1 calc R U . . .
C28 C 0.7471(7) 0.1065(6) 1.0086(5) 0.075(2) Uani 1 1 d . . . . .
C29 C 0.3815(6) 0.4922(5) 0.6601(5) 0.0537(15) Uani 1 1 d . . . . .
C30 C 0.3642(6) 0.4135(5) 0.7618(5) 0.0523(15) Uani 1 1 d . . . . .
C31 C 0.3922(6) 0.4296(5) 0.8566(5) 0.0568(16) Uani 1 1 d . . . . .
H31 H 0.419563 0.494450 0.858376 0.068 Uiso 1 1 calc R U . . .
C32 C 0.3804(7) 0.3508(6) 0.9496(5) 0.0678(19) Uani 1 1 d . . . . .
H32 H 0.398125 0.363085 1.013803 0.081 Uiso 1 1 calc R U . . .
C33 C 0.3423(7) 0.2548(7) 0.9458(6) 0.081(2) Uani 1 1 d . . . . .
C34 C 0.3105(8) 0.2367(7) 0.8510(7) 0.088(2) Uani 1 1 d . . . . .
H34 H 0.283466 0.171569 0.849634 0.106 Uiso 1 1 calc R U . . .
C35 C 0.3201(7) 0.3172(6) 0.7602(5) 0.0682(19) Uani 1 1 d . . . . .
H35 H 0.297013 0.307745 0.696824 0.082 Uiso 1 1 calc R U . . .
C36 C 0.3367(10) 0.1680(9) 1.0414(8) 0.123(4) Uani 1 1 d . . . . .
Cl1A Cl 1.0099(9) 0.3759(5) 0.0490(5) 0.188(4) Uani 0.654(12) 1 d D U P A 1
Cl2A Cl 1.0057(8) 0.1440(5) 0.0930(7) 0.146(3) Uani 0.654(12) 1 d D U P A 1
Cl3A Cl 0.8513(7) 0.2973(5) 0.2159(6) 0.154(3) Uani 0.654(12) 1 d D U P A 1
C37A C 0.9953(13) 0.2629(10) 0.1493(10) 0.098(4) Uani 0.654(12) 1 d D U P A 1
H37A H 1.059841 0.245298 0.198714 0.117 Uiso 0.654(12) 1 calc R U P A 1
Cl1B Cl 0.116(2) 0.3599(16) 0.1157(18) 0.255(10) Uani 0.346(12) 1 d D U P A 2
Cl2B Cl 0.0373(17) 0.183(2) 0.0736(19) 0.224(9) Uani 0.346(12) 1 d D U P A 2
Cl3B Cl -0.1308(14) 0.354(2) 0.1696(17) 0.229(10) Uani 0.346(12) 1 d D U P A 2
C37B C 0.020(2) 0.272(2) 0.163(3) 0.189(9) Uani 0.346(12) 1 d D U P A 2
H37B H 0.043263 0.225948 0.233414 0.227 Uiso 0.346(12) 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
S1 C1 1.700(7) . ?
S1 C2 1.718(6) . ?
O2 C29 1.210(7) . ?
N2 C21 1.137(10) . ?
C2 C3 1.398(9) . ?
C2 C14 1.474(9) . ?
C1 C4 1.402(8) . ?
C1 C7 1.485(8) . ?
N1 C13 1.138(8) . ?
O1 C14 1.214(9) . ?
S2 C4 1.717(7) . ?
S2 C6 1.750(5) . ?
N3 C28 1.130(8) . ?
C3 C4 1.418(7) . ?
C3 C5 1.449(8) . ?
N4 C36 1.132(10) . ?
C5 C6 1.368(8) . ?
C5 C22 1.489(7) . ?
C6 C29 1.486(9) . ?
C7 C8 1.372(9) . ?
C7 C12 1.390(9) . ?
C8 C9 1.397(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.384(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.361(10) . ?
C10 C13 1.456(9) . ?
C11 C12 1.385(9) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C14 C15 1.488(10) . ?
C15 C16 1.383(9) . ?
C15 C20 1.385(9) . ?
C16 C17 1.373(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.384(9) . ?
C18 C21 1.445(11) . ?
C19 C20 1.381(9) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C22 C27 1.380(8) . ?
C22 C23 1.386(8) . ?
C23 C24 1.384(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.390(9) . ?
C24 H24 0.9300 . ?
C25 C26 1.373(9) . ?
C25 C28 1.442(9) . ?
C26 C27 1.392(8) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C29 C30 1.477(8) . ?
C30 C31 1.370(8) . ?
C30 C35 1.401(8) . ?
C31 C32 1.385(8) . ?
C31 H31 0.9300 . ?
C32 C33 1.365(10) . ?
C32 H32 0.9300 . ?
C33 C34 1.397(10) . ?
C33 C36 1.448(10) . ?
C34 C35 1.370(9) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
Cl1A C37A 1.703(12) . ?
Cl2A C37A 1.730(13) . ?
Cl3A C37A 1.755(14) . ?
C37A H37A 0.9800 . ?
Cl1B C37B 1.70(2) . ?
Cl2B C37B 1.72(2) . ?
Cl3B C37B 1.74(2) . ?
C37B H37B 0.9800 . ?

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
C1 S1 C2 94.3(3) . . ?
C3 C2 C14 133.5(6) . . ?
C3 C2 S1 109.6(4) . . ?
C14 C2 S1 116.6(5) . . ?
C4 C1 C7 128.8(6) . . ?
C4 C1 S1 110.3(4) . . ?
C7 C1 S1 120.9(5) . . ?
C4 S2 C6 90.6(3) . . ?
C2 C3 C4 113.0(5) . . ?
C2 C3 C5 134.7(5) . . ?
C4 C3 C5 112.2(6) . . ?
C1 C4 C3 112.6(6) . . ?
C1 C4 S2 135.3(5) . . ?
C3 C4 S2 112.1(4) . . ?
C6 C5 C3 110.4(5) . . ?
C6 C5 C22 126.5(5) . . ?
C3 C5 C22 122.9(5) . . ?
C5 C6 C29 132.1(5) . . ?
C5 C6 S2 114.4(4) . . ?
C29 C6 S2 113.5(4) . . ?
C8 C7 C12 118.4(6) . . ?
C8 C7 C1 121.9(6) . . ?
C12 C7 C1 119.7(6) . . ?
C7 C8 C9 121.6(7) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C10 C9 C8 118.7(7) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C11 C10 C9 120.3(6) . . ?
C11 C10 C13 120.0(7) . . ?
C9 C10 C13 119.6(7) . . ?
C10 C11 C12 120.6(7) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 120.4(7) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
N1 C13 C10 179.3(9) . . ?
O1 C14 C2 120.9(7) . . ?
O1 C14 C15 120.7(7) . . ?
C2 C14 C15 118.3(6) . . ?
C16 C15 C20 119.1(7) . . ?
C16 C15 C14 121.1(7) . . ?
C20 C15 C14 119.8(6) . . ?
C17 C16 C15 119.8(7) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C16 121.0(6) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 119.9(7) . . ?
C17 C18 C21 121.7(7) . . ?
C19 C18 C21 118.4(7) . . ?
C20 C19 C18 119.1(7) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C15 121.0(6) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
N2 C21 C18 179.0(11) . . ?
C27 C22 C23 119.4(5) . . ?
C27 C22 C5 121.6(5) . . ?
C23 C22 C5 118.9(5) . . ?
C24 C23 C22 120.6(6) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 119.6(6) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 120.2(5) . . ?
C26 C25 C28 120.5(6) . . ?
C24 C25 C28 119.3(6) . . ?
C25 C26 C27 119.9(6) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C22 C27 C26 120.4(6) . . ?
C22 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
N3 C28 C25 179.7(10) . . ?
O2 C29 C30 120.7(6) . . ?
O2 C29 C6 119.0(5) . . ?
C30 C29 C6 120.2(5) . . ?
C31 C30 C35 119.1(6) . . ?
C31 C30 C29 122.7(5) . . ?
C35 C30 C29 118.1(6) . . ?
C30 C31 C32 121.1(6) . . ?
C30 C31 H31 119.5 . . ?
C32 C31 H31 119.5 . . ?
C33 C32 C31 119.0(6) . . ?
C33 C32 H32 120.5 . . ?
C31 C32 H32 120.5 . . ?
C32 C33 C34 121.6(6) . . ?
C32 C33 C36 119.6(7) . . ?
C34 C33 C36 118.8(7) . . ?
C35 C34 C33 118.5(7) . . ?
C35 C34 H34 120.7 . . ?
C33 C34 H34 120.7 . . ?
C34 C35 C30 120.7(7) . . ?
C34 C35 H35 119.7 . . ?
C30 C35 H35 119.7 . . ?
N4 C36 C33 178.1(11) . . ?
Cl1A C37A Cl2A 107.4(7) . . ?
Cl1A C37A Cl3A 109.8(8) . . ?
Cl2A C37A Cl3A 108.5(8) . . ?
Cl1A C37A H37A 110.4 . . ?
Cl2A C37A H37A 110.4 . . ?
Cl3A C37A H37A 110.4 . . ?
Cl1B C37B Cl2B 105.2(16) . . ?
Cl1B C37B Cl3B 111.1(18) . . ?
Cl2B C37B Cl3B 109.2(17) . . ?
Cl1B C37B H37B 110.4 . . ?
Cl2B C37B H37B 110.4 . . ?
Cl3B C37B H37B 110.4 . . ?

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
C1 S1 C2 C3 -3.3(5) . . . . ?
C1 S1 C2 C14 171.6(6) . . . . ?
C2 S1 C1 C4 2.0(5) . . . . ?
C2 S1 C1 C7 -176.9(5) . . . . ?
C14 C2 C3 C4 -170.0(8) . . . . ?
S1 C2 C3 C4 3.7(7) . . . . ?
C14 C2 C3 C5 13.6(13) . . . . ?
S1 C2 C3 C5 -172.8(6) . . . . ?
C7 C1 C4 C3 178.6(6) . . . . ?
S1 C1 C4 C3 -0.3(7) . . . . ?
C7 C1 C4 S2 0.6(11) . . . . ?
S1 C1 C4 S2 -178.3(4) . . . . ?
C2 C3 C4 C1 -2.2(8) . . . . ?
C5 C3 C4 C1 175.0(5) . . . . ?
C2 C3 C4 S2 176.2(5) . . . . ?
C5 C3 C4 S2 -6.5(6) . . . . ?
C6 S2 C4 C1 -176.8(7) . . . . ?
C6 S2 C4 C3 5.1(5) . . . . ?
C2 C3 C5 C6 -179.1(7) . . . . ?
C4 C3 C5 C6 4.5(7) . . . . ?
C2 C3 C5 C22 4.6(11) . . . . ?
C4 C3 C5 C22 -171.9(5) . . . . ?
C3 C5 C6 C29 177.5(6) . . . . ?
C22 C5 C6 C29 -6.3(10) . . . . ?
C3 C5 C6 S2 -0.6(6) . . . . ?
C22 C5 C6 S2 175.6(5) . . . . ?
C4 S2 C6 C5 -2.6(5) . . . . ?
C4 S2 C6 C29 178.9(5) . . . . ?
C4 C1 C7 C8 -8.9(10) . . . . ?
S1 C1 C7 C8 169.9(5) . . . . ?
C4 C1 C7 C12 171.5(6) . . . . ?
S1 C1 C7 C12 -9.8(9) . . . . ?
C12 C7 C8 C9 1.8(10) . . . . ?
C1 C7 C8 C9 -177.9(6) . . . . ?
C7 C8 C9 C10 0.3(11) . . . . ?
C8 C9 C10 C11 -1.8(11) . . . . ?
C8 C9 C10 C13 -179.0(6) . . . . ?
C9 C10 C11 C12 1.2(11) . . . . ?
C13 C10 C11 C12 178.4(7) . . . . ?
C10 C11 C12 C7 1.0(11) . . . . ?
C8 C7 C12 C11 -2.4(11) . . . . ?
C1 C7 C12 C11 177.3(6) . . . . ?
C3 C2 C14 O1 -146.7(9) . . . . ?
S1 C2 C14 O1 40.0(11) . . . . ?
C3 C2 C14 C15 35.8(12) . . . . ?
S1 C2 C14 C15 -137.5(6) . . . . ?
O1 C14 C15 C16 32.2(13) . . . . ?
C2 C14 C15 C16 -150.3(7) . . . . ?
O1 C14 C15 C20 -145.2(9) . . . . ?
C2 C14 C15 C20 32.3(10) . . . . ?
C20 C15 C16 C17 -2.6(11) . . . . ?
C14 C15 C16 C17 180.0(7) . . . . ?
C15 C16 C17 C18 0.3(12) . . . . ?
C16 C17 C18 C19 2.8(12) . . . . ?
C16 C17 C18 C21 -177.8(8) . . . . ?
C17 C18 C19 C20 -3.7(11) . . . . ?
C21 C18 C19 C20 176.9(7) . . . . ?
C18 C19 C20 C15 1.4(11) . . . . ?
C16 C15 C20 C19 1.7(11) . . . . ?
C14 C15 C20 C19 179.2(7) . . . . ?
C6 C5 C22 C27 58.1(9) . . . . ?
C3 C5 C22 C27 -126.2(6) . . . . ?
C6 C5 C22 C23 -117.7(7) . . . . ?
C3 C5 C22 C23 58.0(8) . . . . ?
C27 C22 C23 C24 -1.3(10) . . . . ?
C5 C22 C23 C24 174.6(6) . . . . ?
C22 C23 C24 C25 0.5(10) . . . . ?
C23 C24 C25 C26 0.9(10) . . . . ?
C23 C24 C25 C28 -179.9(7) . . . . ?
C24 C25 C26 C27 -1.5(10) . . . . ?
C28 C25 C26 C27 179.3(6) . . . . ?
C23 C22 C27 C26 0.8(9) . . . . ?
C5 C22 C27 C26 -175.1(6) . . . . ?
C25 C26 C27 C22 0.6(10) . . . . ?
C5 C6 C29 O2 -153.2(7) . . . . ?
S2 C6 C29 O2 24.9(8) . . . . ?
C5 C6 C29 C30 27.6(10) . . . . ?
S2 C6 C29 C30 -154.2(5) . . . . ?
O2 C29 C30 C31 -140.3(7) . . . . ?
C6 C29 C30 C31 38.8(9) . . . . ?
O2 C29 C30 C35 41.2(9) . . . . ?
C6 C29 C30 C35 -139.7(6) . . . . ?
C35 C30 C31 C32 1.6(10) . . . . ?
C29 C30 C31 C32 -176.8(6) . . . . ?
C30 C31 C32 C33 1.2(11) . . . . ?
C31 C32 C33 C34 -2.5(12) . . . . ?
C31 C32 C33 C36 176.2(8) . . . . ?
C32 C33 C34 C35 1.0(13) . . . . ?
C36 C33 C34 C35 -177.7(9) . . . . ?
C33 C34 C35 C30 1.9(12) . . . . ?
C31 C30 C35 C34 -3.2(11) . . . . ?
C29 C30 C35 C34 175.3(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C37B H37B N2 0.98 2.33 3.23(4) 151.7 2_656 yes

_refine_diff_density_max         0.739
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.074




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: deuterated chloroform'
####################################################################### 
# 
# 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_B14319F1
_database_code_depnum_ccdc_archive 'CCDC 2194534'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2022-08-03 deposited with the CCDC.	2022-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
;
'4,4'-(5-(4-cyanophenyl)thiophene-2,3-dicarbonyl)dibenzonitrile'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H13 N3 O2 S'
_chemical_formula_sum            'C27 H13 N3 O2 S'
_chemical_formula_weight         443.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.6659(8)
_cell_length_b                   12.4099(6)
_cell_length_c                   19.1062(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.991(4)
_cell_angle_gamma                90
_cell_volume                     4392.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8649
_cell_measurement_theta_min      2.2880
_cell_measurement_theta_max      27.4400

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             1824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.177
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.996
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 5 0.0686
-5 -4 -1 0.0288
-1 0 0 0.0023
1 0 0 0.0163
0 -1 -5 0.0467
1 1 1 0.0372
5 4 -2 0.0557
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku mm003 (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Double bounce MaxFlux multilayer optic'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Pro: Kappa single'
_diffrn_detector                 'Dectris Pilatus200K 3R'
_diffrn_reflns_number            48311
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.291
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_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             7755
_reflns_number_gt                5104
_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.
;

_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0899P)²+0.4100P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7751
_refine_ls_number_parameters     681
_refine_ls_number_restraints     282
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1546
_refine_ls_wR_factor_gt          0.1350
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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_1 N 1.07311(19) 0.4078(3) 0.84965(16) 0.1340(12) Uani 1 1 d . . . . .
O1_1 O 0.72250(9) 0.45952(14) 0.39650(9) 0.0735(5) Uani 1 1 d . . . . .
S1_1 S 0.88136(5) 0.17150(7) 0.49291(5) 0.0542(3) Uani 0.857(3) 1 d D U P A 1
C1_1 C 0.8653(4) 0.2841(5) 0.5416(2) 0.0489(15) Uani 0.857(3) 1 d D . P A 1
C2_1 C 0.8112(4) 0.3419(5) 0.5073(4) 0.0563(14) Uani 0.857(3) 1 d D U P A 1
H2_1 H 0.793503 0.403974 0.526423 0.068 Uiso 0.857(3) 1 calc R U P A 1
C3_1 C 0.7835(3) 0.3029(6) 0.4413(3) 0.0466(10) Uani 0.857(3) 1 d D U P A 1
C4_1 C 0.8172(4) 0.2089(4) 0.4247(3) 0.0473(11) Uani 0.857(3) 1 d D U P A 1
S1B_1 S 0.7961(7) 0.3768(10) 0.5141(6) 0.071(3) Uani 0.143(3) 1 d D U P A 2
C1B_1 C 0.854(3) 0.276(4) 0.5445(16) 0.0489(15) Uani 0.143(3) 1 d D . P A 2
C2B_1 C 0.8666(13) 0.212(2) 0.4893(13) 0.067(5) Uani 0.143(3) 1 d D U P A 2
H2B_1 H 0.902737 0.159649 0.492469 0.080 Uiso 0.143(3) 1 calc R U P A 2
C3B_1 C 0.820(3) 0.231(3) 0.4274(17) 0.055(5) Uani 0.143(3) 1 d D U P A 2
C4B_1 C 0.771(2) 0.311(4) 0.4355(18) 0.049(4) Uani 0.143(3) 1 d D U P A 2
O2_1 O 0.82922(13) 0.04986(15) 0.36476(10) 0.1004(7) Uani 1 1 d . . . . .
N2_1 N 0.45489(15) 0.0972(2) 0.19143(17) 0.1177(11) Uani 1 1 d . . . . .
N3_1 N 0.68868(16) 0.3769(2) 0.04573(12) 0.0992(9) Uani 1 1 d . . . . .
C5_1 C 0.90639(11) 0.30493(19) 0.61060(11) 0.0517(6) Uani 1 1 d . . . . .
C6_1 C 0.90899(15) 0.4078(2) 0.63720(13) 0.0762(8) Uani 1 1 d . . . . .
H6_1 H 0.882500 0.462004 0.612396 0.091 Uiso 1 1 calc R U . . .
C7_1 C 0.95051(16) 0.4322(2) 0.70052(14) 0.0834(8) Uani 1 1 d . . . . .
H7_1 H 0.951750 0.502320 0.717853 0.100 Uiso 1 1 calc R U . . .
C8_1 C 0.98968(13) 0.3527(2) 0.73739(12) 0.0649(7) Uani 1 1 d . . . . .
C9_1 C 0.98589(13) 0.2496(2) 0.71226(13) 0.0681(7) Uani 1 1 d . . . . .
H9_1 H 1.011047 0.195144 0.738159 0.082 Uiso 1 1 calc R U . . .
C10_1 C 0.94542(12) 0.2250(2) 0.64922(11) 0.0594(6) Uani 1 1 d . . . . .
H10_1 H 0.944191 0.154591 0.632418 0.071 Uiso 1 1 calc R U . . .
C11_1 C 1.03575(18) 0.3811(3) 0.80055(15) 0.0950(10) Uani 1 1 d . . . . .
C12_1 C 0.72187(12) 0.36151(19) 0.39660(11) 0.0512(5) Uani 1 1 d . . . . .
C13_1 C 0.66281(11) 0.30197(16) 0.35481(11) 0.0461(5) Uani 1 1 d . . . . .
C14_1 C 0.62673(11) 0.35243(19) 0.29588(12) 0.0543(6) Uani 1 1 d . . . . .
H14_1 H 0.639213 0.422370 0.284744 0.065 Uiso 1 1 calc R U . . .
C15_1 C 0.57275(12) 0.2999(2) 0.25390(12) 0.0609(6) Uani 1 1 d . . . . .
H15_1 H 0.549384 0.333542 0.213995 0.073 Uiso 1 1 calc R U . . .
C16_1 C 0.55341(11) 0.1969(2) 0.27127(12) 0.0577(6) Uani 1 1 d . . . . .
C17_1 C 0.58717(12) 0.14716(19) 0.33124(12) 0.0570(6) Uani 1 1 d . . . . .
H17_1 H 0.572793 0.078737 0.343663 0.068 Uiso 1 1 calc R U . . .
C18_1 C 0.64224(11) 0.19949(18) 0.37248(12) 0.0533(6) Uani 1 1 d . . . . .
H18_1 H 0.665613 0.165702 0.412321 0.064 Uiso 1 1 calc R U . . .
C19_1 C 0.49806(15) 0.1411(2) 0.22734(15) 0.0788(8) Uani 1 1 d . . . . .
C20_1 C 0.81326(13) 0.1451(2) 0.36062(12) 0.0612(6) Uani 1 1 d . . . . .
C21_1 C 0.79103(12) 0.19571(18) 0.29099(11) 0.0518(6) Uani 1 1 d . . . . .
C22_1 C 0.74906(13) 0.13664(19) 0.23974(11) 0.0593(6) Uani 1 1 d . . . . .
H22_1 H 0.738028 0.065160 0.248393 0.071 Uiso 1 1 calc R U . . .
C23_1 C 0.72368(13) 0.1831(2) 0.17624(11) 0.0606(6) Uani 1 1 d . . . . .
H23_1 H 0.694571 0.143785 0.142435 0.073 Uiso 1 1 calc R U . . .
C24_1 C 0.74161(12) 0.2884(2) 0.16291(11) 0.0570(6) Uani 1 1 d . . . . .
C25_1 C 0.78639(12) 0.3469(2) 0.21185(11) 0.0577(6) Uani 1 1 d . . . . .
H25_1 H 0.799957 0.416688 0.201627 0.069 Uiso 1 1 calc R U . . .
C26_1 C 0.81085(11) 0.30049(19) 0.27626(11) 0.0531(6) Uani 1 1 d . . . . .
H26_1 H 0.840588 0.339511 0.309719 0.064 Uiso 1 1 calc R U . . .
C27_1 C 0.71229(15) 0.3384(2) 0.09663(13) 0.0727(7) Uani 1 1 d . . . . .
N1_2 N 1.02042(13) 0.6520(2) 0.62099(12) 0.0954(8) Uani 1 1 d . . . . .
O1_2 O 0.65577(10) 0.53279(14) 0.17394(9) 0.0755(5) Uani 1 1 d . . . . .
S1_2 S 0.82726(6) 0.82285(9) 0.25064(6) 0.0565(4) Uani 0.757(3) 1 d D U P B 1
C1_2 C 0.8093(6) 0.7217(8) 0.3065(5) 0.048(3) Uani 0.757(3) 1 d D . P B 1
C2_2 C 0.7575(3) 0.6570(4) 0.2752(3) 0.0526(14) Uani 0.757(3) 1 d D U P B 1
H2_2 H 0.742431 0.595309 0.296967 0.063 Uiso 0.757(3) 1 calc R U P B 1
C3_2 C 0.7279(5) 0.6883(9) 0.2083(5) 0.0463(15) Uani 0.757(3) 1 d D U P B 1
C4_2 C 0.7610(5) 0.7804(5) 0.1862(4) 0.0468(13) Uani 0.757(3) 1 d D U P B 1
S1B_2 S 0.7427(3) 0.6160(4) 0.2840(3) 0.0582(13) Uani 0.243(3) 1 d D U P B 2
C1B_2 C 0.8156(16) 0.699(2) 0.3021(15) 0.040(7) Uani 0.243(3) 1 d D . P B 2
C2B_2 C 0.8104(8) 0.7767(12) 0.2522(9) 0.073(4) Uani 0.243(3) 1 d D U P B 2
H2B_2 H 0.836248 0.840798 0.257712 0.088 Uiso 0.243(3) 1 calc R U P B 2
C3B_2 C 0.7634(17) 0.753(2) 0.1921(12) 0.053(4) Uani 0.243(3) 1 d D U P B 2
C4B_2 C 0.7163(18) 0.673(3) 0.2037(14) 0.044(4) Uani 0.243(3) 1 d D U P B 2
O2_2 O 0.77260(12) 0.93214(16) 0.12237(10) 0.0947(6) Uani 1 1 d . . . . .
N2_2 N 0.39690(15) 0.9057(2) -0.03443(17) 0.1101(10) Uani 1 1 d . . . . .
N3_2 N 0.64255(19) 0.6007(2) -0.19475(14) 0.1172(11) Uani 1 1 d . . . . .
C5_2 C 0.85495(11) 0.70510(19) 0.37469(11) 0.0521(5) Uani 1 1 d . . . . .
C6_2 C 0.88120(12) 0.7939(2) 0.41328(12) 0.0586(6) Uani 1 1 d . . . . .
H6_2 H 0.870852 0.862661 0.395445 0.070 Uiso 1 1 calc R U . . .
C7_2 C 0.92230(12) 0.7824(2) 0.47747(12) 0.0610(6) Uani 1 1 d . . . . .
H7_2 H 0.939140 0.842885 0.503099 0.073 Uiso 1 1 calc R U . . .
C8_2 C 0.93842(12) 0.6810(2) 0.50366(11) 0.0578(6) Uani 1 1 d . . . . .
C9_2 C 0.91341(13) 0.5916(2) 0.46585(13) 0.0714(7) Uani 1 1 d . . . . .
H9_2 H 0.924522 0.523107 0.483649 0.086 Uiso 1 1 calc R U . . .
C10_2 C 0.87181(13) 0.6035(2) 0.40145(13) 0.0672(7) Uani 1 1 d . . . . .
H10_2 H 0.855043 0.542833 0.375944 0.081 Uiso 1 1 calc R U . . .
C11_2 C 0.98355(14) 0.6663(2) 0.57024(13) 0.0705(7) Uani 1 1 d . . . . .
C12_2 C 0.66225(12) 0.62946(19) 0.16773(11) 0.0533(6) Uani 1 1 d . . . . .
C13_2 C 0.60519(11) 0.69205(18) 0.12372(11) 0.0497(5) Uani 1 1 d . . . . .
C14_2 C 0.58780(12) 0.79639(19) 0.14060(12) 0.0549(6) Uani 1 1 d . . . . .
H14_2 H 0.612936 0.829721 0.179732 0.066 Uiso 1 1 calc R U . . .
C15_2 C 0.53371(11) 0.8515(2) 0.10014(12) 0.0591(6) Uani 1 1 d . . . . .
H15_2 H 0.521741 0.921194 0.112327 0.071 Uiso 1 1 calc R U . . .
C16_2 C 0.49739(12) 0.8026(2) 0.04140(13) 0.0607(6) Uani 1 1 d . . . . .
C17_2 C 0.51417(13) 0.6978(2) 0.02384(13) 0.0666(7) Uani 1 1 d . . . . .
H17_2 H 0.489414 0.665153 -0.015751 0.080 Uiso 1 1 calc R U . . .
C18_2 C 0.56765(12) 0.6421(2) 0.06523(12) 0.0588(6) Uani 1 1 d . . . . .
H18_2 H 0.578494 0.571469 0.054037 0.071 Uiso 1 1 calc R U . . .
C19_2 C 0.44094(15) 0.8607(2) -0.00134(15) 0.0800(8) Uani 1 1 d . . . . .
C20_2 C 0.75637(13) 0.8362(2) 0.12123(12) 0.0610(6) Uani 1 1 d . . . . .
C21_2 C 0.73344(11) 0.78148(19) 0.05327(11) 0.0518(5) Uani 1 1 d . . . . .
C22_2 C 0.75085(12) 0.67501(19) 0.04132(11) 0.0569(6) Uani 1 1 d . . . . .
H22_2 H 0.777753 0.635401 0.076564 0.068 Uiso 1 1 calc R U . . .
C23_2 C 0.72812(13) 0.6278(2) -0.02312(12) 0.0627(6) Uani 1 1 d . . . . .
H23_2 H 0.739956 0.556666 -0.031725 0.075 Uiso 1 1 calc R U . . .
C24_2 C 0.68765(13) 0.6876(2) -0.07456(11) 0.0602(6) Uani 1 1 d . . . . .
C25_2 C 0.67115(13) 0.7944(2) -0.06331(12) 0.0622(6) Uani 1 1 d . . . . .
H25_2 H 0.644425 0.834052 -0.098661 0.075 Uiso 1 1 calc R U . . .
C26_2 C 0.69442(12) 0.84125(19) 0.00016(12) 0.0589(6) Uani 1 1 d . . . . .
H26_2 H 0.684105 0.913305 0.007807 0.071 Uiso 1 1 calc R U . . .
C27_2 C 0.66242(17) 0.6382(2) -0.14174(14) 0.0818(8) 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_1 C11_1 1.148(3) . ?
O1_1 C12_1 1.216(3) . ?
S1_1 C4_1 1.723(5) . ?
S1_1 C1_1 1.725(5) . ?
C1_1 C2_1 1.343(6) . ?
C1_1 C5_1 1.465(5) . ?
C2_1 C3_1 1.391(7) . ?
C3_1 C4_1 1.381(4) . ?
C3_1 C12_1 1.530(5) . ?
C4_1 C20_1 1.452(5) . ?
S1B_1 C1B_1 1.717(18) . ?
S1B_1 C4B_1 1.723(17) . ?
C1B_1 C2B_1 1.360(16) . ?
C1B_1 C5_1 1.54(3) . ?
C2B_1 C3B_1 1.40(2) . ?
C3B_1 C4B_1 1.373(16) . ?
C3B_1 C20_1 1.66(2) . ?
C4B_1 C12_1 1.27(3) . ?
O2_1 C20_1 1.219(3) . ?
N2_1 C19_1 1.133(3) . ?
N3_1 C27_1 1.124(3) . ?
C5_1 C6_1 1.372(3) . ?
C5_1 C10_1 1.389(3) . ?
C6_1 C7_1 1.389(3) . ?
C7_1 C8_1 1.371(4) . ?
C8_1 C9_1 1.366(4) . ?
C8_1 C11_1 1.438(3) . ?
C9_1 C10_1 1.376(3) . ?
C12_1 C13_1 1.478(3) . ?
C13_1 C18_1 1.382(3) . ?
C13_1 C14_1 1.389(3) . ?
C14_1 C15_1 1.374(3) . ?
C15_1 C16_1 1.379(3) . ?
C16_1 C17_1 1.384(3) . ?
C16_1 C19_1 1.429(3) . ?
C17_1 C18_1 1.379(3) . ?
C20_1 C21_1 1.484(3) . ?
C21_1 C22_1 1.387(3) . ?
C21_1 C26_1 1.390(3) . ?
C22_1 C23_1 1.374(3) . ?
C23_1 C24_1 1.380(3) . ?
C24_1 C25_1 1.382(3) . ?
C24_1 C27_1 1.456(3) . ?
C25_1 C26_1 1.385(3) . ?
N1_2 C11_2 1.133(3) . ?
O1_2 C12_2 1.213(3) . ?
S1_2 C1_2 1.707(7) . ?
S1_2 C4_2 1.717(7) . ?
C1_2 C2_2 1.341(8) . ?
C1_2 C5_2 1.482(6) . ?
C2_2 C3_2 1.387(8) . ?
C3_2 C4_2 1.388(6) . ?
C3_2 C12_2 1.551(6) . ?
C4_2 C20_2 1.415(6) . ?
S1B_2 C1B_2 1.705(17) . ?
S1B_2 C4B_2 1.708(17) . ?
C1B_2 C2B_2 1.354(16) . ?
C1B_2 C5_2 1.49(2) . ?
C2B_2 C3B_2 1.388(19) . ?
C3B_2 C4B_2 1.364(15) . ?
C3B_2 C20_2 1.692(18) . ?
C4B_2 C12_2 1.271(19) . ?
O2_2 C20_2 1.228(3) . ?
N2_2 C19_2 1.123(3) . ?
N3_2 C27_2 1.135(3) . ?
C5_2 C6_2 1.382(3) . ?
C5_2 C10_2 1.382(3) . ?
C6_2 C7_2 1.373(3) . ?
C7_2 C8_2 1.373(3) . ?
C8_2 C9_2 1.374(3) . ?
C8_2 C11_2 1.449(3) . ?
C9_2 C10_2 1.381(3) . ?
C12_2 C13_2 1.492(3) . ?
C13_2 C14_2 1.383(3) . ?
C13_2 C18_2 1.391(3) . ?
C14_2 C15_2 1.376(3) . ?
C15_2 C16_2 1.379(3) . ?
C16_2 C17_2 1.388(4) . ?
C16_2 C19_2 1.445(3) . ?
C17_2 C18_2 1.381(3) . ?
C20_2 C21_2 1.482(3) . ?
C21_2 C22_2 1.386(3) . ?
C21_2 C26_2 1.389(3) . ?
C22_2 C23_2 1.383(3) . ?
C23_2 C24_2 1.381(3) . ?
C24_2 C25_2 1.383(3) . ?
C24_2 C27_2 1.449(4) . ?
C25_2 C26_2 1.367(3) . ?

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
C4_1 S1_1 C1_1 92.27(18) . . ?
C2_1 C1_1 C5_1 128.7(4) . . ?
C2_1 C1_1 S1_1 109.8(3) . . ?
C5_1 C1_1 S1_1 121.5(3) . . ?
C1_1 C2_1 C3_1 115.6(4) . . ?
C4_1 C3_1 C2_1 111.8(3) . . ?
C4_1 C3_1 C12_1 127.3(4) . . ?
C2_1 C3_1 C12_1 120.8(4) . . ?
C3_1 C4_1 C20_1 132.5(4) . . ?
C3_1 C4_1 S1_1 110.4(3) . . ?
C20_1 C4_1 S1_1 116.8(3) . . ?
C1B_1 S1B_1 C4B_1 92.4(13) . . ?
C2B_1 C1B_1 C5_1 129(3) . . ?
C2B_1 C1B_1 S1B_1 108.9(14) . . ?
C5_1 C1B_1 S1B_1 114(2) . . ?
C1B_1 C2B_1 C3B_1 114.2(15) . . ?
C4B_1 C3B_1 C2B_1 112.5(16) . . ?
C4B_1 C3B_1 C20_1 124(2) . . ?
C2B_1 C3B_1 C20_1 122(2) . . ?
C12_1 C4B_1 C3B_1 137(2) . . ?
C12_1 C4B_1 S1B_1 112.1(19) . . ?
C3B_1 C4B_1 S1B_1 109.1(15) . . ?
C6_1 C5_1 C10_1 118.4(2) . . ?
C6_1 C5_1 C1_1 119.2(3) . . ?
C10_1 C5_1 C1_1 122.4(3) . . ?
C6_1 C5_1 C1B_1 121.0(11) . . ?
C10_1 C5_1 C1B_1 120.3(13) . . ?
C5_1 C6_1 C7_1 121.1(2) . . ?
C8_1 C7_1 C6_1 119.8(3) . . ?
C9_1 C8_1 C7_1 119.5(2) . . ?
C9_1 C8_1 C11_1 121.6(2) . . ?
C7_1 C8_1 C11_1 118.8(3) . . ?
C8_1 C9_1 C10_1 121.0(2) . . ?
C9_1 C10_1 C5_1 120.2(2) . . ?
N1_1 C11_1 C8_1 177.1(4) . . ?
O1_1 C12_1 C4B_1 119(2) . . ?
O1_1 C12_1 C13_1 120.4(2) . . ?
C4B_1 C12_1 C13_1 120(2) . . ?
O1_1 C12_1 C3_1 118.0(3) . . ?
C13_1 C12_1 C3_1 121.6(3) . . ?
C18_1 C13_1 C14_1 119.4(2) . . ?
C18_1 C13_1 C12_1 122.64(19) . . ?
C14_1 C13_1 C12_1 117.9(2) . . ?
C15_1 C14_1 C13_1 120.5(2) . . ?
C14_1 C15_1 C16_1 119.6(2) . . ?
C15_1 C16_1 C17_1 120.4(2) . . ?
C15_1 C16_1 C19_1 120.0(2) . . ?
C17_1 C16_1 C19_1 119.6(2) . . ?
C18_1 C17_1 C16_1 119.7(2) . . ?
C17_1 C18_1 C13_1 120.2(2) . . ?
N2_1 C19_1 C16_1 178.7(3) . . ?
O2_1 C20_1 C4_1 119.1(3) . . ?
O2_1 C20_1 C21_1 120.5(2) . . ?
C4_1 C20_1 C21_1 120.4(3) . . ?
O2_1 C20_1 C3B_1 125.3(13) . . ?
C21_1 C20_1 C3B_1 114.0(14) . . ?
C22_1 C21_1 C26_1 119.5(2) . . ?
C22_1 C21_1 C20_1 118.8(2) . . ?
C26_1 C21_1 C20_1 121.7(2) . . ?
C23_1 C22_1 C21_1 120.4(2) . . ?
C22_1 C23_1 C24_1 119.7(2) . . ?
C23_1 C24_1 C25_1 120.8(2) . . ?
C23_1 C24_1 C27_1 119.4(2) . . ?
C25_1 C24_1 C27_1 119.8(2) . . ?
C24_1 C25_1 C26_1 119.3(2) . . ?
C25_1 C26_1 C21_1 120.1(2) . . ?
N3_1 C27_1 C24_1 179.0(3) . . ?
C1_2 S1_2 C4_2 92.5(3) . . ?
C2_2 C1_2 C5_2 127.9(6) . . ?
C2_2 C1_2 S1_2 110.4(5) . . ?
C5_2 C1_2 S1_2 121.1(5) . . ?
C1_2 C2_2 C3_2 115.3(6) . . ?
C2_2 C3_2 C4_2 111.7(5) . . ?
C2_2 C3_2 C12_2 122.0(5) . . ?
C4_2 C3_2 C12_2 126.2(6) . . ?
C3_2 C4_2 C20_2 133.3(6) . . ?
C3_2 C4_2 S1_2 110.1(4) . . ?
C20_2 C4_2 S1_2 116.2(4) . . ?
C1B_2 S1B_2 C4B_2 93.9(10) . . ?
C2B_2 C1B_2 C5_2 127.0(17) . . ?
C2B_2 C1B_2 S1B_2 107.5(11) . . ?
C5_2 C1B_2 S1B_2 120.7(15) . . ?
C1B_2 C2B_2 C3B_2 114.7(13) . . ?
C4B_2 C3B_2 C2B_2 111.8(15) . . ?
C4B_2 C3B_2 C20_2 125.8(17) . . ?
C2B_2 C3B_2 C20_2 121.0(15) . . ?
C12_2 C4B_2 C3B_2 135.1(18) . . ?
C12_2 C4B_2 S1B_2 115.6(15) . . ?
C3B_2 C4B_2 S1B_2 109.2(13) . . ?
C6_2 C5_2 C10_2 118.7(2) . . ?
C6_2 C5_2 C1_2 119.1(4) . . ?
C10_2 C5_2 C1_2 122.2(4) . . ?
C6_2 C5_2 C1B_2 129.9(11) . . ?
C10_2 C5_2 C1B_2 111.1(12) . . ?
C7_2 C6_2 C5_2 121.1(2) . . ?
C6_2 C7_2 C8_2 119.7(2) . . ?
C7_2 C8_2 C9_2 120.2(2) . . ?
C7_2 C8_2 C11_2 120.9(2) . . ?
C9_2 C8_2 C11_2 118.9(2) . . ?
C8_2 C9_2 C10_2 120.1(2) . . ?
C9_2 C10_2 C5_2 120.3(2) . . ?
N1_2 C11_2 C8_2 177.3(3) . . ?
O1_2 C12_2 C4B_2 116.8(14) . . ?
O1_2 C12_2 C13_2 119.8(2) . . ?
C4B_2 C12_2 C13_2 123.2(15) . . ?
O1_2 C12_2 C3_2 120.0(4) . . ?
C13_2 C12_2 C3_2 120.2(4) . . ?
C14_2 C13_2 C18_2 119.7(2) . . ?
C14_2 C13_2 C12_2 121.8(2) . . ?
C18_2 C13_2 C12_2 118.4(2) . . ?
C15_2 C14_2 C13_2 120.8(2) . . ?
C14_2 C15_2 C16_2 119.5(2) . . ?
C15_2 C16_2 C17_2 120.4(2) . . ?
C15_2 C16_2 C19_2 119.5(2) . . ?
C17_2 C16_2 C19_2 120.1(2) . . ?
C18_2 C17_2 C16_2 120.0(2) . . ?
C17_2 C18_2 C13_2 119.7(2) . . ?
N2_2 C19_2 C16_2 179.8(4) . . ?
O2_2 C20_2 C4_2 118.0(3) . . ?
O2_2 C20_2 C21_2 120.3(2) . . ?
C4_2 C20_2 C21_2 121.7(3) . . ?
O2_2 C20_2 C3B_2 125.4(9) . . ?
C21_2 C20_2 C3B_2 114.1(9) . . ?
C22_2 C21_2 C26_2 120.1(2) . . ?
C22_2 C21_2 C20_2 122.2(2) . . ?
C26_2 C21_2 C20_2 117.7(2) . . ?
C23_2 C22_2 C21_2 119.8(2) . . ?
C24_2 C23_2 C22_2 119.2(2) . . ?
C23_2 C24_2 C25_2 121.1(2) . . ?
C23_2 C24_2 C27_2 119.6(2) . . ?
C25_2 C24_2 C27_2 119.3(2) . . ?
C26_2 C25_2 C24_2 119.5(2) . . ?
C25_2 C26_2 C21_2 120.2(2) . . ?
N3_2 C27_2 C24_2 179.1(3) . . ?

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
C4_1 S1_1 C1_1 C2_1 2.8(7) . . . . ?
C4_1 S1_1 C1_1 C5_1 -178.6(6) . . . . ?
C5_1 C1_1 C2_1 C3_1 178.7(8) . . . . ?
S1_1 C1_1 C2_1 C3_1 -2.9(10) . . . . ?
C1_1 C2_1 C3_1 C4_1 1.3(11) . . . . ?
C1_1 C2_1 C3_1 C12_1 -179.8(7) . . . . ?
C2_1 C3_1 C4_1 C20_1 -172.3(8) . . . . ?
C12_1 C3_1 C4_1 C20_1 9.0(16) . . . . ?
C2_1 C3_1 C4_1 S1_1 0.9(10) . . . . ?
C12_1 C3_1 C4_1 S1_1 -177.8(7) . . . . ?
C1_1 S1_1 C4_1 C3_1 -2.1(7) . . . . ?
C1_1 S1_1 C4_1 C20_1 172.2(6) . . . . ?
C4B_1 S1B_1 C1B_1 C2B_1 15(5) . . . . ?
C4B_1 S1B_1 C1B_1 C5_1 167(4) . . . . ?
C5_1 C1B_1 C2B_1 C3B_1 -158(5) . . . . ?
S1B_1 C1B_1 C2B_1 C3B_1 -11(6) . . . . ?
C1B_1 C2B_1 C3B_1 C4B_1 0(7) . . . . ?
C1B_1 C2B_1 C3B_1 C20_1 -166(4) . . . . ?
C2B_1 C3B_1 C4B_1 C12_1 175(6) . . . . ?
C20_1 C3B_1 C4B_1 C12_1 -19(12) . . . . ?
C2B_1 C3B_1 C4B_1 S1B_1 12(7) . . . . ?
C20_1 C3B_1 C4B_1 S1B_1 177(4) . . . . ?
C1B_1 S1B_1 C4B_1 C12_1 176(5) . . . . ?
C1B_1 S1B_1 C4B_1 C3B_1 -15(5) . . . . ?
C2_1 C1_1 C5_1 C6_1 -22.2(10) . . . . ?
S1_1 C1_1 C5_1 C6_1 159.5(4) . . . . ?
C2_1 C1_1 C5_1 C10_1 160.5(7) . . . . ?
S1_1 C1_1 C5_1 C10_1 -17.8(8) . . . . ?
C2B_1 C1B_1 C5_1 C6_1 139(4) . . . . ?
S1B_1 C1B_1 C5_1 C6_1 -6(5) . . . . ?
C2B_1 C1B_1 C5_1 C10_1 -49(6) . . . . ?
S1B_1 C1B_1 C5_1 C10_1 166(2) . . . . ?
C10_1 C5_1 C6_1 C7_1 1.1(4) . . . . ?
C1_1 C5_1 C6_1 C7_1 -176.4(4) . . . . ?
C1B_1 C5_1 C6_1 C7_1 174(3) . . . . ?
C5_1 C6_1 C7_1 C8_1 0.0(4) . . . . ?
C6_1 C7_1 C8_1 C9_1 -1.7(4) . . . . ?
C6_1 C7_1 C8_1 C11_1 176.2(3) . . . . ?
C7_1 C8_1 C9_1 C10_1 2.4(4) . . . . ?
C11_1 C8_1 C9_1 C10_1 -175.5(3) . . . . ?
C8_1 C9_1 C10_1 C5_1 -1.3(4) . . . . ?
C6_1 C5_1 C10_1 C9_1 -0.5(4) . . . . ?
C1_1 C5_1 C10_1 C9_1 177.0(4) . . . . ?
C1B_1 C5_1 C10_1 C9_1 -173(3) . . . . ?
C3B_1 C4B_1 C12_1 O1_1 -128(7) . . . . ?
S1B_1 C4B_1 C12_1 O1_1 36(5) . . . . ?
C3B_1 C4B_1 C12_1 C13_1 55(9) . . . . ?
S1B_1 C4B_1 C12_1 C13_1 -141(2) . . . . ?
C4_1 C3_1 C12_1 O1_1 -142.3(8) . . . . ?
C2_1 C3_1 C12_1 O1_1 39.0(10) . . . . ?
C4_1 C3_1 C12_1 C13_1 37.9(11) . . . . ?
C2_1 C3_1 C12_1 C13_1 -140.7(6) . . . . ?
O1_1 C12_1 C13_1 C18_1 -153.6(2) . . . . ?
C4B_1 C12_1 C13_1 C18_1 23(3) . . . . ?
C3_1 C12_1 C13_1 C18_1 26.1(5) . . . . ?
O1_1 C12_1 C13_1 C14_1 25.9(3) . . . . ?
C4B_1 C12_1 C13_1 C14_1 -157(3) . . . . ?
C3_1 C12_1 C13_1 C14_1 -154.4(4) . . . . ?
C18_1 C13_1 C14_1 C15_1 -2.3(3) . . . . ?
C12_1 C13_1 C14_1 C15_1 178.2(2) . . . . ?
C13_1 C14_1 C15_1 C16_1 1.2(4) . . . . ?
C14_1 C15_1 C16_1 C17_1 1.1(4) . . . . ?
C14_1 C15_1 C16_1 C19_1 -179.1(2) . . . . ?
C15_1 C16_1 C17_1 C18_1 -2.3(3) . . . . ?
C19_1 C16_1 C17_1 C18_1 177.9(2) . . . . ?
C16_1 C17_1 C18_1 C13_1 1.2(3) . . . . ?
C14_1 C13_1 C18_1 C17_1 1.1(3) . . . . ?
C12_1 C13_1 C18_1 C17_1 -179.4(2) . . . . ?
C3_1 C4_1 C20_1 O2_1 -156.5(9) . . . . ?
S1_1 C4_1 C20_1 O2_1 30.7(7) . . . . ?
C3_1 C4_1 C20_1 C21_1 24.3(12) . . . . ?
S1_1 C4_1 C20_1 C21_1 -148.5(4) . . . . ?
C4B_1 C3B_1 C20_1 O2_1 -142(5) . . . . ?
C2B_1 C3B_1 C20_1 O2_1 22(6) . . . . ?
C4B_1 C3B_1 C20_1 C21_1 43(6) . . . . ?
C2B_1 C3B_1 C20_1 C21_1 -153(4) . . . . ?
O2_1 C20_1 C21_1 C22_1 37.5(4) . . . . ?
C4_1 C20_1 C21_1 C22_1 -143.3(4) . . . . ?
C3B_1 C20_1 C21_1 C22_1 -147(2) . . . . ?
O2_1 C20_1 C21_1 C26_1 -142.9(3) . . . . ?
C4_1 C20_1 C21_1 C26_1 36.3(5) . . . . ?
C3B_1 C20_1 C21_1 C26_1 32(2) . . . . ?
C26_1 C21_1 C22_1 C23_1 -3.7(3) . . . . ?
C20_1 C21_1 C22_1 C23_1 175.9(2) . . . . ?
C21_1 C22_1 C23_1 C24_1 1.6(3) . . . . ?
C22_1 C23_1 C24_1 C25_1 1.8(3) . . . . ?
C22_1 C23_1 C24_1 C27_1 -177.7(2) . . . . ?
C23_1 C24_1 C25_1 C26_1 -2.9(3) . . . . ?
C27_1 C24_1 C25_1 C26_1 176.5(2) . . . . ?
C24_1 C25_1 C26_1 C21_1 0.7(3) . . . . ?
C22_1 C21_1 C26_1 C25_1 2.6(3) . . . . ?
C20_1 C21_1 C26_1 C25_1 -177.0(2) . . . . ?
C4_2 S1_2 C1_2 C2_2 2.7(10) . . . . ?
C4_2 S1_2 C1_2 C5_2 174.5(10) . . . . ?
C5_2 C1_2 C2_2 C3_2 -174.4(12) . . . . ?
S1_2 C1_2 C2_2 C3_2 -3.4(14) . . . . ?
C1_2 C2_2 C3_2 C4_2 2.3(15) . . . . ?
C1_2 C2_2 C3_2 C12_2 -173.6(11) . . . . ?
C2_2 C3_2 C4_2 C20_2 171.9(9) . . . . ?
C12_2 C3_2 C4_2 C20_2 -12(2) . . . . ?
C2_2 C3_2 C4_2 S1_2 -0.1(13) . . . . ?
C12_2 C3_2 C4_2 S1_2 175.6(10) . . . . ?
C1_2 S1_2 C4_2 C3_2 -1.5(10) . . . . ?
C1_2 S1_2 C4_2 C20_2 -175.0(8) . . . . ?
C4B_2 S1B_2 C1B_2 C2B_2 10(3) . . . . ?
C4B_2 S1B_2 C1B_2 C5_2 167(3) . . . . ?
C5_2 C1B_2 C2B_2 C3B_2 -173(3) . . . . ?
S1B_2 C1B_2 C2B_2 C3B_2 -17(4) . . . . ?
C1B_2 C2B_2 C3B_2 C4B_2 19(4) . . . . ?
C1B_2 C2B_2 C3B_2 C20_2 -174(3) . . . . ?
C2B_2 C3B_2 C4B_2 C12_2 175(4) . . . . ?
C20_2 C3B_2 C4B_2 C12_2 8(7) . . . . ?
C2B_2 C3B_2 C4B_2 S1B_2 -10(4) . . . . ?
C20_2 C3B_2 C4B_2 S1B_2 -177(2) . . . . ?
C1B_2 S1B_2 C4B_2 C12_2 176(3) . . . . ?
C1B_2 S1B_2 C4B_2 C3B_2 0(3) . . . . ?
C2_2 C1_2 C5_2 C6_2 -151.6(11) . . . . ?
S1_2 C1_2 C5_2 C6_2 38.2(12) . . . . ?
C2_2 C1_2 C5_2 C10_2 27.8(17) . . . . ?
S1_2 C1_2 C5_2 C10_2 -142.3(7) . . . . ?
C2B_2 C1B_2 C5_2 C6_2 15(5) . . . . ?
S1B_2 C1B_2 C5_2 C6_2 -137.0(16) . . . . ?
C2B_2 C1B_2 C5_2 C10_2 -158(3) . . . . ?
S1B_2 C1B_2 C5_2 C10_2 50(3) . . . . ?
C10_2 C5_2 C6_2 C7_2 -1.0(4) . . . . ?
C1_2 C5_2 C6_2 C7_2 178.5(6) . . . . ?
C1B_2 C5_2 C6_2 C7_2 -174(2) . . . . ?
C5_2 C6_2 C7_2 C8_2 0.7(4) . . . . ?
C6_2 C7_2 C8_2 C9_2 -0.1(4) . . . . ?
C6_2 C7_2 C8_2 C11_2 178.1(2) . . . . ?
C7_2 C8_2 C9_2 C10_2 -0.2(4) . . . . ?
C11_2 C8_2 C9_2 C10_2 -178.4(2) . . . . ?
C8_2 C9_2 C10_2 C5_2 -0.1(4) . . . . ?
C6_2 C5_2 C10_2 C9_2 0.7(4) . . . . ?
C1_2 C5_2 C10_2 C9_2 -178.8(7) . . . . ?
C1B_2 C5_2 C10_2 C9_2 174.8(16) . . . . ?
C3B_2 C4B_2 C12_2 O1_2 141(5) . . . . ?
S1B_2 C4B_2 C12_2 O1_2 -33(4) . . . . ?
C3B_2 C4B_2 C12_2 C13_2 -43(6) . . . . ?
S1B_2 C4B_2 C12_2 C13_2 142.0(17) . . . . ?
C2_2 C3_2 C12_2 O1_2 -35.3(14) . . . . ?
C4_2 C3_2 C12_2 O1_2 149.4(10) . . . . ?
C2_2 C3_2 C12_2 C13_2 141.9(9) . . . . ?
C4_2 C3_2 C12_2 C13_2 -33.4(15) . . . . ?
O1_2 C12_2 C13_2 C14_2 146.2(2) . . . . ?
C4B_2 C12_2 C13_2 C14_2 -29(2) . . . . ?
C3_2 C12_2 C13_2 C14_2 -31.0(6) . . . . ?
O1_2 C12_2 C13_2 C18_2 -32.2(3) . . . . ?
C4B_2 C12_2 C13_2 C18_2 153(2) . . . . ?
C3_2 C12_2 C13_2 C18_2 150.6(6) . . . . ?
C18_2 C13_2 C14_2 C15_2 0.0(3) . . . . ?
C12_2 C13_2 C14_2 C15_2 -178.4(2) . . . . ?
C13_2 C14_2 C15_2 C16_2 -1.2(3) . . . . ?
C14_2 C15_2 C16_2 C17_2 1.3(4) . . . . ?
C14_2 C15_2 C16_2 C19_2 -179.6(2) . . . . ?
C15_2 C16_2 C17_2 C18_2 -0.2(4) . . . . ?
C19_2 C16_2 C17_2 C18_2 -179.3(2) . . . . ?
C16_2 C17_2 C18_2 C13_2 -1.0(4) . . . . ?
C14_2 C13_2 C18_2 C17_2 1.1(3) . . . . ?
C12_2 C13_2 C18_2 C17_2 179.5(2) . . . . ?
C3_2 C4_2 C20_2 O2_2 156.3(11) . . . . ?
S1_2 C4_2 C20_2 O2_2 -32.0(8) . . . . ?
C3_2 C4_2 C20_2 C21_2 -24.3(14) . . . . ?
S1_2 C4_2 C20_2 C21_2 147.3(4) . . . . ?
C4B_2 C3B_2 C20_2 O2_2 143(3) . . . . ?
C2B_2 C3B_2 C20_2 O2_2 -23(3) . . . . ?
C4B_2 C3B_2 C20_2 C21_2 -42(4) . . . . ?
C2B_2 C3B_2 C20_2 C21_2 153(2) . . . . ?
O2_2 C20_2 C21_2 C22_2 144.6(3) . . . . ?
C4_2 C20_2 C21_2 C22_2 -34.7(6) . . . . ?
C3B_2 C20_2 C21_2 C22_2 -31.0(13) . . . . ?
O2_2 C20_2 C21_2 C26_2 -34.1(3) . . . . ?
C4_2 C20_2 C21_2 C26_2 146.6(5) . . . . ?
C3B_2 C20_2 C21_2 C26_2 150.2(13) . . . . ?
C26_2 C21_2 C22_2 C23_2 -1.2(3) . . . . ?
C20_2 C21_2 C22_2 C23_2 -179.9(2) . . . . ?
C21_2 C22_2 C23_2 C24_2 -0.6(3) . . . . ?
C22_2 C23_2 C24_2 C25_2 1.7(4) . . . . ?
C22_2 C23_2 C24_2 C27_2 -178.8(2) . . . . ?
C23_2 C24_2 C25_2 C26_2 -0.9(4) . . . . ?
C27_2 C24_2 C25_2 C26_2 179.6(2) . . . . ?
C24_2 C25_2 C26_2 C21_2 -0.9(4) . . . . ?
C22_2 C21_2 C26_2 C25_2 2.0(3) . . . . ?
C20_2 C21_2 C26_2 C25_2 -179.2(2) . . . . ?

_refine_diff_density_max         0.354
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.042





####################################################################### 
# 
# 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_B14515_twin_hklf5
_database_code_depnum_ccdc_archive 'CCDC 2195876'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2022-08-09 deposited with the CCDC.	2022-11-08 downloaded from the CCDC.
;
_audit_creation_date             2022-08-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
'1,4-diazabicyclo[2.2.2]octan-1-ium 2-(4-isopropylphenyl)-2-oxoethanedithioate'
;
_chemical_formula_moiety         'C11 H11 O S2, C6 H13 N2'
_chemical_formula_sum            'C17 H24 N2 O S2'
_chemical_formula_weight         336.50
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.9171(10)
_cell_length_b                   11.5193(10)
_cell_length_c                   10.7037(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.827(7)
_cell_angle_gamma                90
_cell_volume                     1817.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7425
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8040
_cell_measurement_theta_min      2.3300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -5 4 0.1007
0 5 1 0.0880
1 -5 -5 0.1402
0 -5 -2 0.1385
1 0 0 0.0127
-1 0 0 0.0097
-5 2 3 0.0830
14 8 7 0.0655
6 4 -15 0.1597
1 5 0 0.0765
-2 1 5 0.1040

_exptl_crystal_size_max          0.287
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.022
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9625 -5.0198 3.9790 -0.3958 0.0919 0.0094
-0.0159 4.9894 1.0216 0.1807 -0.0369 -0.2552
0.9984 -4.9648 -5.0228 -0.0063 0.0022 0.4517
0.0119 -4.9836 -2.0211 -0.1400 0.0165 0.3044
0.9986 0.0016 -0.0032 0.0117 0.0466 -0.0003
-0.9986 -0.0016 0.0032 -0.0117 -0.0466 0.0003
-4.9888 1.9730 3.0234 -0.0918 -0.1948 -0.2283
13.9764 7.9737 6.9870 0.2328 0.7029 -0.6789
5.9152 4.0920 -14.9939 0.8574 -0.0710 0.5715
0.9786 4.9967 0.0189 0.2331 -0.0106 -0.2063
-1.9810 0.9671 5.0083 -0.1825 -0.0030 -0.2866

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7441
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_min         2.244
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  90.00   0.50   30.00    --    1.00  57.00 -60.00  236
  2  ω    -30.00  90.00   0.50   30.00    --    1.00  38.00-180.00  240
  3  ω     44.00  90.00   0.50   30.00    --    1.00  38.00-180.00   92
  4  ω    -30.00   3.00   0.50   30.00    --    1.00  38.00-180.00   66
  5  ω     -3.00  86.00   0.50   30.00    --   -1.30  57.00-120.00  178
  6  ω     42.00  82.00   0.50   30.00    --   -1.30  38.00 150.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0114851000
_diffrn_orient_matrix_UB_12      0.0445454000
_diffrn_orient_matrix_UB_13      -0.0404950000
_diffrn_orient_matrix_UB_21      0.0467301000
_diffrn_orient_matrix_UB_22      -0.0113474000
_diffrn_orient_matrix_UB_23      0.0200726000
_diffrn_orient_matrix_UB_31      -0.0004439000
_diffrn_orient_matrix_UB_32      -0.0410109000
_diffrn_orient_matrix_UB_33      -0.0494819000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5260
_reflns_number_total             7441
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         7441
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      0.994
_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)+(0.0695P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1173
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6281(11)
 0.3719(11)
2. 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
3. Restrained distances
 S1-C1 \\sim S1A-C1
 with sigma of 0.02
 S2-C1 \\sim S2A-C1
 with sigma of 0.02
 O1-C2 \\sim O1A-C2
 with sigma of 0.02
4. Others
 Sof(S1A)=Sof(S2A)=Sof(O1A)=1-FVAR(1)
 Sof(S1)=Sof(S2)=Sof(O1)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C5'(H5'A,H5'B), C6'(H6'A,H6'B), C1'(H1'A,H1'B), C7'(H7'A,H7'B), C2'(H2'A,
 H2'B), C4'(H4'A,H4'B)
5.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C4(H4), C5(H5)
5.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
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 0.4191(3) 0.6258(4) 0.1257(5) 0.0878(13) Uani 0.60(3) 1 d D . P A 1
S2 S 0.4503(3) 0.4457(4) 0.3344(4) 0.0724(9) Uani 0.60(3) 1 d D . P A 1
N1' N 0.63419(12) 0.57939(15) 0.22752(15) 0.0578(4) Uani 1 1 d . . . . .
O1 O 0.2546(10) 0.4228(8) 0.1357(11) 0.0761(19) Uani 0.60(3) 1 d D . P A 1
C6 C 0.12301(13) 0.68607(15) 0.43621(16) 0.0517(4) Uani 1 1 d . . . . .
C3 C 0.23200(12) 0.56812(15) 0.28724(16) 0.0493(4) Uani 1 1 d . . . . .
C8 C 0.13993(13) 0.54761(16) 0.27332(17) 0.0549(4) Uani 1 1 d . . . . .
H8 H 0.113941 0.493362 0.214289 0.066 Uiso 1 1 calc R U . . .
C7 C 0.08601(13) 0.60625(17) 0.34551(18) 0.0563(5) Uani 1 1 d . . . . .
H7 H 0.023875 0.592259 0.333404 0.068 Uiso 1 1 calc R U . . .
C4 C 0.26958(13) 0.64836(16) 0.37651(17) 0.0546(4) Uani 1 1 d . . . . .
H4 H 0.331529 0.663472 0.387181 0.066 Uiso 1 1 calc R U . . .
C5 C 0.21511(13) 0.70608(16) 0.44984(17) 0.0582(5) Uani 1 1 d . . . . .
H5 H 0.241219 0.759576 0.509665 0.070 Uiso 1 1 calc R U . . .
C2 C 0.28704(14) 0.50391(19) 0.20508(19) 0.0630(5) Uani 1 1 d D . . . .
C1 C 0.38708(14) 0.52527(18) 0.22038(18) 0.0597(5) Uani 1 1 d D . . . .
C9 C 0.06478(15) 0.74942(18) 0.51729(17) 0.0651(5) Uani 1 1 d . . . . .
H9 H 0.105764 0.788195 0.584831 0.078 Uiso 1 1 calc R U . . .
C5' C 0.67157(17) 0.46051(19) 0.2225(2) 0.0748(6) Uani 1 1 d . . . . .
H5'A H 0.650841 0.425660 0.140687 0.090 Uiso 1 1 calc R U . . .
H5'B H 0.651611 0.412237 0.287223 0.090 Uiso 1 1 calc R U . . .
C6' C 0.67030(16) 0.6537(2) 0.13414(19) 0.0699(6) Uani 1 1 d . . . . .
H6'A H 0.641760 0.729529 0.130452 0.084 Uiso 1 1 calc R U . . .
H6'B H 0.658164 0.618757 0.050797 0.084 Uiso 1 1 calc R U . . .
C1' C 0.65846(16) 0.6295(2) 0.35651(18) 0.0716(6) Uani 1 1 d . . . . .
H1'A H 0.629843 0.585752 0.417021 0.086 Uiso 1 1 calc R U . . .
H1'B H 0.638437 0.709602 0.357564 0.086 Uiso 1 1 calc R U . . .
C7' C 0.77227(17) 0.6651(2) 0.1764(2) 0.0789(6) Uani 1 1 d . . . . .
H7'A H 0.803808 0.647258 0.105994 0.095 Uiso 1 1 calc R U . . .
H7'B H 0.786564 0.744599 0.202116 0.095 Uiso 1 1 calc R U . . .
C10 C 0.00490(17) 0.6705(2) 0.5794(2) 0.0840(7) Uani 1 1 d . . . . .
H10A H -0.040636 0.637516 0.516244 0.126 Uiso 1 1 calc R U . . .
H10B H -0.023801 0.714028 0.638727 0.126 Uiso 1 1 calc R U . . .
H10C H 0.040791 0.609476 0.622909 0.126 Uiso 1 1 calc R U . . .
C2' C 0.76150(17) 0.6226(2) 0.3897(2) 0.0828(7) Uani 1 1 d . . . . .
H2'A H 0.784990 0.697965 0.418940 0.099 Uiso 1 1 calc R U . . .
H2'B H 0.777294 0.567547 0.458109 0.099 Uiso 1 1 calc R U . . .
C4' C 0.77356(17) 0.4703(2) 0.2444(3) 0.0869(7) Uani 1 1 d . . . . .
H4'A H 0.798463 0.415984 0.309812 0.104 Uiso 1 1 calc R U . . .
H4'B H 0.796516 0.449425 0.167367 0.104 Uiso 1 1 calc R U . . .
C11 C 0.0087(2) 0.8430(2) 0.4427(3) 0.1082(10) Uani 1 1 d . . . . .
H11A H 0.048297 0.898918 0.413014 0.162 Uiso 1 1 calc R U . . .
H11B H -0.028563 0.880912 0.495934 0.162 Uiso 1 1 calc R U . . .
H11C H -0.029210 0.808605 0.371721 0.162 Uiso 1 1 calc R U . . .
H1' H 0.5755(16) 0.5750(17) 0.2136(19) 0.060(6) Uiso 1 1 d . . . . .
N3' N 0.80375(12) 0.58692(18) 0.28182(17) 0.0763(5) Uani 1 1 d . . . . .
S1A S 0.4227(3) 0.6348(5) 0.1378(8) 0.0691(14) Uani 0.40(3) 1 d D . P A 2
S2A S 0.4447(6) 0.4315(9) 0.3057(18) 0.110(2) Uani 0.40(3) 1 d D . P A 2
O1A O 0.2468(14) 0.459(2) 0.1074(17) 0.089(4) Uani 0.40(3) 1 d D . 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
S1 C1 1.657(5) . ?
S2 C1 1.693(4) . ?
N1' C5' 1.483(3) . ?
N1' C6' 1.479(3) . ?
N1' C1' 1.489(2) . ?
N1' H1' 0.87(2) . ?
O1 C2 1.244(9) . ?
C6 C7 1.389(3) . ?
C6 C5 1.379(3) . ?
C6 C9 1.507(3) . ?
C3 C8 1.379(2) . ?
C3 C4 1.385(2) . ?
C3 C2 1.489(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.375(3) . ?
C7 H7 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.384(3) . ?
C5 H5 0.9300 . ?
C2 C1 1.496(3) . ?
C2 O1A 1.237(13) . ?
C1 S1A 1.673(5) . ?
C1 S2A 1.581(9) . ?
C9 H9 0.9800 . ?
C9 C10 1.499(3) . ?
C9 C11 1.515(3) . ?
C5' H5'A 0.9700 . ?
C5' H5'B 0.9700 . ?
C5' C4' 1.508(3) . ?
C6' H6'A 0.9700 . ?
C6' H6'B 0.9700 . ?
C6' C7' 1.525(3) . ?
C1' H1'A 0.9700 . ?
C1' H1'B 0.9700 . ?
C1' C2' 1.526(3) . ?
C7' H7'A 0.9700 . ?
C7' H7'B 0.9700 . ?
C7' N3' 1.464(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C2' H2'A 0.9700 . ?
C2' H2'B 0.9700 . ?
C2' N3' 1.457(3) . ?
C4' H4'A 0.9700 . ?
C4' H4'B 0.9700 . ?
C4' N3' 1.453(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
C5' N1' C1' 110.64(17) . . ?
C5' N1' H1' 108.4(13) . . ?
C6' N1' C5' 109.40(16) . . ?
C6' N1' C1' 109.90(17) . . ?
C6' N1' H1' 112.4(13) . . ?
C1' N1' H1' 106.1(13) . . ?
C7 C6 C9 121.38(17) . . ?
C5 C6 C7 117.87(17) . . ?
C5 C6 C9 120.75(17) . . ?
C8 C3 C4 118.69(16) . . ?
C8 C3 C2 118.79(16) . . ?
C4 C3 C2 122.53(17) . . ?
C3 C8 H8 119.5 . . ?
C7 C8 C3 120.92(17) . . ?
C7 C8 H8 119.5 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 120.93(17) . . ?
C8 C7 H7 119.5 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.10(17) . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 121.47(17) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
O1 C2 C3 121.8(7) . . ?
O1 C2 C1 118.6(7) . . ?
C3 C2 C1 119.00(17) . . ?
O1A C2 C3 117.8(10) . . ?
O1A C2 C1 120.6(10) . . ?
S1 C1 S2 129.7(2) . . ?
C2 C1 S1 115.1(2) . . ?
C2 C1 S2 115.20(19) . . ?
C2 C1 S1A 117.3(2) . . ?
C2 C1 S2A 113.3(3) . . ?
S2A C1 S1A 129.2(3) . . ?
C6 C9 H9 107.2 . . ?
C6 C9 C11 111.19(16) . . ?
C10 C9 C6 113.39(18) . . ?
C10 C9 H9 107.2 . . ?
C10 C9 C11 110.3(2) . . ?
C11 C9 H9 107.2 . . ?
N1' C5' H5'A 110.2 . . ?
N1' C5' H5'B 110.2 . . ?
N1' C5' C4' 107.53(19) . . ?
H5'A C5' H5'B 108.5 . . ?
C4' C5' H5'A 110.2 . . ?
C4' C5' H5'B 110.2 . . ?
N1' C6' H6'A 110.2 . . ?
N1' C6' H6'B 110.2 . . ?
N1' C6' C7' 107.44(16) . . ?
H6'A C6' H6'B 108.5 . . ?
C7' C6' H6'A 110.2 . . ?
C7' C6' H6'B 110.2 . . ?
N1' C1' H1'A 110.4 . . ?
N1' C1' H1'B 110.4 . . ?
N1' C1' C2' 106.76(17) . . ?
H1'A C1' H1'B 108.6 . . ?
C2' C1' H1'A 110.4 . . ?
C2' C1' H1'B 110.4 . . ?
C6' C7' H7'A 109.4 . . ?
C6' C7' H7'B 109.4 . . ?
H7'A C7' H7'B 108.0 . . ?
N3' C7' C6' 111.28(18) . . ?
N3' C7' H7'A 109.4 . . ?
N3' C7' H7'B 109.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1' C2' H2'A 109.2 . . ?
C1' C2' H2'B 109.2 . . ?
H2'A C2' H2'B 107.9 . . ?
N3' C2' C1' 111.91(17) . . ?
N3' C2' H2'A 109.2 . . ?
N3' C2' H2'B 109.2 . . ?
C5' C4' H4'A 109.2 . . ?
C5' C4' H4'B 109.2 . . ?
H4'A C4' H4'B 107.9 . . ?
N3' C4' C5' 112.00(19) . . ?
N3' C4' H4'A 109.2 . . ?
N3' C4' H4'B 109.2 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2' N3' C7' 108.1(2) . . ?
C4' N3' C7' 107.88(18) . . ?
C4' N3' C2' 109.0(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
N1' C5' C4' N3' 8.6(3) . . . . ?
N1' C6' C7' N3' 8.6(3) . . . . ?
N1' C1' C2' N3' 8.5(3) . . . . ?
O1 C2 C1 S1 95.7(6) . . . . ?
O1 C2 C1 S2 -85.9(6) . . . . ?
C3 C8 C7 C6 -1.3(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C3 C2 C1 S1 -93.3(3) . . . . ?
C3 C2 C1 S2 85.2(3) . . . . ?
C3 C2 C1 S1A -87.4(4) . . . . ?
C3 C2 C1 S2A 97.6(8) . . . . ?
C8 C3 C4 C5 0.1(3) . . . . ?
C8 C3 C2 O1 -8.9(7) . . . . ?
C8 C3 C2 C1 -179.61(18) . . . . ?
C8 C3 C2 O1A 18.6(14) . . . . ?
C7 C6 C5 C4 -0.4(3) . . . . ?
C7 C6 C9 C10 50.5(2) . . . . ?
C7 C6 C9 C11 -74.4(3) . . . . ?
C4 C3 C8 C7 0.6(3) . . . . ?
C4 C3 C2 O1 171.7(6) . . . . ?
C4 C3 C2 C1 0.9(3) . . . . ?
C4 C3 C2 O1A -160.9(14) . . . . ?
C5 C6 C7 C8 1.2(3) . . . . ?
C5 C6 C9 C10 -129.7(2) . . . . ?
C5 C6 C9 C11 105.4(2) . . . . ?
C2 C3 C8 C7 -178.87(18) . . . . ?
C2 C3 C4 C5 179.60(19) . . . . ?
C9 C6 C7 C8 -179.01(18) . . . . ?
C9 C6 C5 C4 179.76(17) . . . . ?
C5' N1' C6' C7' -65.6(2) . . . . ?
C5' N1' C1' C2' 55.1(2) . . . . ?
C5' C4' N3' C7' -64.1(3) . . . . ?
C5' C4' N3' C2' 53.0(3) . . . . ?
C6' N1' C5' C4' 56.1(2) . . . . ?
C6' N1' C1' C2' -65.8(2) . . . . ?
C6' C7' N3' C2' -64.1(2) . . . . ?
C6' C7' N3' C4' 53.6(2) . . . . ?
C1' N1' C5' C4' -65.2(2) . . . . ?
C1' N1' C6' C7' 56.1(2) . . . . ?
C1' C2' N3' C7' 53.8(3) . . . . ?
C1' C2' N3' C4' -63.2(3) . . . . ?
O1A C2 C1 S1A 73.9(13) . . . . ?
O1A C2 C1 S2A -101.1(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 1.452
_oxdiff_exptl_absorpt_empirical_full_min 0.490
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.6281(11) 13971 17049 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.3719(11) 14036 17049 nmt -0.9997 0.0002 -0.4277 0.0003 -0.9998 -0.0002
0.0001 -0.0001 0.9996

_twin_special_details            
;
Component 2 rotated by 179.9816° 
around [-0.21 0.00 0.98] (reciprocal) or [0.00 -0.00 1.00] (direct)
;

####################################################################### 
# 
# 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_B14572
_database_code_depnum_ccdc_archive 'CCDC 2194329'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2022-08-02 deposited with the CCDC.	2022-11-08 downloaded from the CCDC.
;
_audit_creation_date             2022-04-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_chemical_formula_moiety         'C32 H16 Br4 O2 S2'
_chemical_formula_sum            'C32 H16 Br4 O2 S2'
_chemical_formula_weight         816.229

_chemical_name_systematic        
;
'(3,6-bis(3-bromophenyl)thieno[3,4-b]thiophene-2,4-diyl)bis
((3-bromophenyl)methanone)'
;
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95570 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.86690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   12.9600(9)
_cell_length_b                   15.6784(9)
_cell_length_c                   15.0197(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.769(7)
_cell_angle_gamma                90
_cell_volume                     2853.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11359
_cell_measurement_theta_max      27.6400
_cell_measurement_theta_min      2.5810
_exptl_absorpt_coefficient_mu    5.818
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.321
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.900
_exptl_crystal_F_000             1584
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0.0232
-1 0 1 0.0100
2 0 1 0.1020
-2 0 -1 0.1045
-1 5 -4 0.0857
1 -5 4 0.0869
-1 -5 -3 0.0738
1 5 4 0.0861

_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0032 0.0098 -1.0040 0.0263 0.0553 0.0130
-1.0032 -0.0098 1.0040 -0.0263 -0.0553 -0.0130
2.0084 0.0021 0.9988 0.0315 0.0727 -0.1195
-2.0084 -0.0021 -0.9988 -0.0315 -0.0727 0.1195
-1.0301 5.0177 -3.9780 0.2134 -0.0886 0.2248
1.0301 -5.0177 3.9780 -0.2134 0.0886 -0.2248
-0.9826 -4.9846 -3.0346 -0.2027 0.0915 0.1858
0.9833 4.9788 4.0369 0.1956 -0.1041 -0.2343

_exptl_crystal_description       pinnacoid
_exptl_crystal_colour            yellow
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.9969
_diffrn_reflns_Laue_measured_fraction_max 0.9972
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            52554
_diffrn_reflns_point_group_measured_fraction_full 0.9969
_diffrn_reflns_point_group_measured_fraction_max 0.9972
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.89
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9972
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  90.00   0.50   45.00    --    1.00  57.00  90.00  236
  2  ω    -28.00  81.00   0.50   45.00    --    1.00  57.00-180.00  218
  3  ω     48.00  82.00   0.50   45.00    --    1.00  57.00 -30.00   68
  4  ω      5.00  89.00   0.50   45.00    --    1.00  38.00 -90.00  168
  5  ω    -31.00  88.00   0.50   45.00    --   -1.30  57.00 150.00  238
  6  ω      2.00  28.00   0.50   45.00    --   -1.30  57.00-120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0189946000
_diffrn_orient_matrix_UB_12      0.0410517000
_diffrn_orient_matrix_UB_13      -0.0067932000
_diffrn_orient_matrix_UB_21      0.0425395000
_diffrn_orient_matrix_UB_22      -0.0189948000
_diffrn_orient_matrix_UB_23      -0.0127123000
_diffrn_orient_matrix_UB_31      -0.0354551000
_diffrn_orient_matrix_UB_32      -0.0008339000
_diffrn_orient_matrix_UB_33      -0.0483859000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -15
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -9
_reflns_number_gt                4568
_reflns_number_total             5603
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         1.3030
_refine_diff_density_min         -0.7358
_refine_diff_density_rms         0.0974
_refine_ls_d_res_high            0.8100
_refine_ls_d_res_low             7.0507
_refine_ls_goodness_of_fit_ref   1.0836
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    41
_refine_ls_number_parameters     500
_refine_ls_number_reflns         5603
_refine_ls_number_restraints     260
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.0570
_refine_ls_shift/su_max          -0.0009
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0261P)²+5.7477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0961
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C5-C20 \\sim C5-C20B
 with sigma of 0.02
3. Rigid bond restraints
 Br3, C20, C21, C22, C23, C24, C25
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 Br3B, C20B, C21B, C22B, C23B, C24B, C25B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Br3 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim Br3B
\\sim C20B \\sim C21B \\sim C22B \\sim C23B \\sim C24B \\sim C25B: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
5. Others
 Sof(Br3B)=Sof(C20B)=Sof(C21B)=Sof(H21B)=Sof(C22B)=Sof(H22B)=Sof(C23B)=
 Sof(H23B)=Sof(C24B)=Sof(C25B)=Sof(H25B)=1-FVAR(1)
 Sof(Br3)=Sof(C20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(C23)=Sof(H23)=Sof(C24)=
 Sof(H24)=Sof(C25)=Sof(H25)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C11(H11), C12(H12), C15(H15), C17(H17), C18(H18), C19(H19),
 C21(H21), C23(H23), C24(H24), C25(H25), C21B(H21B), C22B(H22B), C23B(H23B),
 C25B(H25B), C28(H28), C30(H30), C31(H31), C32(H32)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_group
C1 C 0.2589(3) 0.4112(2) 0.5340(2) 0.0370(8) Uani 1.000000 . . .
O1 O 0.0132(2) 0.4984(2) 0.2530(2) 0.0586(8) Uani 1.000000 . . .
S1 S 0.13752(8) 0.45432(6) 0.45698(6) 0.0425(2) Uani 1.000000 . . .
Br1 Br 0.46877(10) 0.21692(8) 0.82945(8) 0.0782(5) Uani 1.000000 . . .
C2 C 0.1873(3) 0.4679(2) 0.3657(2) 0.0389(8) Uani 1.000000 . . .
O2 O 0.6630(3) 0.3805(2) 0.4690(2) 0.0661(9) Uani 1.000000 . . .
S2 S 0.47044(8) 0.37371(6) 0.52378(6) 0.0422(2) Uani 1.000000 . . .
Br2 Br 0.10476(13) 0.62814(9) -0.05351(8) 0.0843(6) Uani 1.000000 . . .
C3 C 0.2942(3) 0.4363(2) 0.3921(2) 0.0355(8) Uani 1.000000 . . .
C4 C 0.3335(3) 0.4060(2) 0.4879(2) 0.0360(8) Uani 1.000000 . . .
Br4 Br 0.41388(11) 0.19649(8) 0.07452(8) 0.0731(5) Uani 1.000000 . . .
C5 C 0.3740(3) 0.4234(2) 0.3460(2) 0.0388(8) Uani 1.000000 D . .
C6 C 0.4715(3) 0.3914(2) 0.4090(2) 0.0384(8) Uani 1.000000 . . .
C7 C 0.2705(3) 0.3857(2) 0.6309(2) 0.0367(8) Uani 1.000000 . . .
C8 C 0.3527(3) 0.3280(2) 0.6797(3) 0.0436(9) Uani 1.000000 . . .
H8 H 0.4005(3) 0.3069(2) 0.6511(3) 0.0524(10) Uiso 1.000000 R . .
C9 C 0.3635(3) 0.3024(3) 0.7698(3) 0.0478(9) Uani 1.000000 . . .
C10 C 0.2949(4) 0.3330(3) 0.8151(3) 0.0531(10) Uani 1.000000 . . .
H10 H 0.3036(4) 0.3154(3) 0.8765(3) 0.0637(13) Uiso 1.000000 R . .
C11 C 0.2133(3) 0.3904(3) 0.7670(3) 0.0514(10) Uani 1.000000 . . .
H11 H 0.1662(3) 0.4116(3) 0.7962(3) 0.0617(12) Uiso 1.000000 R . .
C12 C 0.2011(3) 0.4165(2) 0.6762(3) 0.0427(9) Uani 1.000000 . . .
H12 H 0.1458(3) 0.4553(2) 0.6449(3) 0.0512(10) Uiso 1.000000 R . .
C13 C 0.1122(3) 0.5102(2) 0.2790(2) 0.0417(8) Uani 1.000000 . . .
C14 C 0.1603(3) 0.5716(2) 0.2278(3) 0.0401(8) Uani 1.000000 . . .
C15 C 0.1146(4) 0.5752(3) 0.1291(3) 0.0481(10) Uani 1.000000 . . .
H15 H 0.0557(4) 0.5401(3) 0.0961(3) 0.0577(11) Uiso 1.000000 R . .
C16 C 0.1572(4) 0.6312(3) 0.0804(3) 0.0525(10) Uani 1.000000 . . .
C17 C 0.2405(4) 0.6861(3) 0.1287(3) 0.0619(12) Uani 1.000000 . . .
H17 H 0.2669(4) 0.7252(3) 0.0953(3) 0.0742(14) Uiso 1.000000 R . .
C18 C 0.2856(4) 0.6831(3) 0.2274(3) 0.0582(11) Uani 1.000000 . . .
H18 H 0.3421(4) 0.7204(3) 0.2601(3) 0.0698(13) Uiso 1.000000 R . .
C19 C 0.2470(3) 0.6250(2) 0.2771(3) 0.0467(9) Uani 1.000000 . . .
H19 H 0.2788(3) 0.6218(2) 0.3431(3) 0.0561(11) Uiso 1.000000 R . .
Br3 Br 0.14888(6) 0.34658(6) -0.01007(5) 0.0652(3) Uani 0.6343(16) . U 1
C20 C 0.3602(13) 0.4426(11) 0.2452(8) 0.030(2) Uani 0.6343(16) D U 1
C21 C 0.2770(10) 0.3986(9) 0.1763(9) 0.037(2) Uani 0.6343(16) . U 1
H21 H 0.2302(10) 0.3632(9) 0.1942(9) 0.044(2) Uiso 0.6343(16) R . 1
C22 C 0.2632(8) 0.4069(7) 0.0817(7) 0.0410(18) Uani 0.6343(16) . U 1
C23 C 0.3302(9) 0.4599(7) 0.0527(8) 0.050(2) Uani 0.6343(16) . U 1
H23 H 0.3205(9) 0.4660(7) -0.0114(8) 0.060(2) Uiso 0.6343(16) R . 1
C24 C 0.4126(8) 0.5038(6) 0.1225(6) 0.051(2) Uani 0.6343(16) . U 1
H24 H 0.4581(8) 0.5401(6) 0.1040(6) 0.061(2) Uiso 0.6343(16) R . 1
C25 C 0.4300(10) 0.4962(10) 0.2173(9) 0.043(2) Uani 0.6343(16) . U 1
H25 H 0.4869(10) 0.5259(10) 0.2624(9) 0.052(3) Uiso 0.6343(16) R . 1
Br3B Br 0.45018(17) 0.55365(12) 0.04924(13) 0.0979(8) Uani 0.3657(16) . U 2
C20B C 0.333(2) 0.427(2) 0.2385(15) 0.034(4) Uani 0.3657(16) D U 2
C21B C 0.2468(19) 0.3844(16) 0.1783(17) 0.043(4) Uani 0.3657(16) . U 2
H21B H 0.2031(19) 0.3515(16) 0.2025(17) 0.052(5) Uiso 0.3657(16) R . 2
C22B C 0.2217(17) 0.3889(13) 0.0804(13) 0.057(4) Uani 0.3657(16) . U 2
H22B H 0.1627(17) 0.3583(13) 0.0388(13) 0.069(5) Uiso 0.3657(16) R . 2
C23B C 0.2840(18) 0.4380(14) 0.0474(15) 0.063(4) Uani 0.3657(16) . U 2
H23B H 0.2688(18) 0.4383(14) -0.0179(15) 0.075(4) Uiso 0.3657(16) R . 2
C24B C 0.3625(18) 0.4842(13) 0.0987(15) 0.055(3) Uani 0.3657(16) . U 2
C25B C 0.3956(17) 0.4824(17) 0.2044(16) 0.041(4) Uani 0.3657(16) . U 2
H25B H 0.4530(17) 0.5154(17) 0.2445(16) 0.050(4) Uiso 0.3657(16) R . 2
C26 C 0.5794(3) 0.3729(2) 0.3985(3) 0.0443(9) Uani 1.000000 . . .
C27 C 0.5848(3) 0.3452(2) 0.3055(3) 0.0453(9) Uani 1.000000 . . .
C28 C 0.5094(3) 0.2904(2) 0.2451(3) 0.0438(9) Uani 1.000000 . . .
H28 H 0.4531(3) 0.2674(2) 0.2624(3) 0.0526(10) Uiso 1.000000 R . .
C29 C 0.5178(4) 0.2696(3) 0.1587(3) 0.0503(10) Uani 1.000000 . . .
C30 C 0.6006(4) 0.3036(3) 0.1320(4) 0.0643(12) Uani 1.000000 . . .
H30 H 0.6049(4) 0.2903(3) 0.0730(4) 0.0772(15) Uiso 1.000000 R . .
C31 C 0.6771(5) 0.3574(3) 0.1936(4) 0.0723(14) Uani 1.000000 . . .
H31 H 0.7331(5) 0.3804(3) 0.1760(4) 0.0868(17) Uiso 1.000000 R . .
C32 C 0.6714(4) 0.3773(3) 0.2810(4) 0.0619(12) Uani 1.000000 . . .
H32 H 0.7249(4) 0.4119(3) 0.3232(4) 0.0743(14) Uiso 1.000000 R . .

loop_
_atom_site_anharm_GC_C_label
_atom_site_anharm_GC_C_111
_atom_site_anharm_GC_C_112
_atom_site_anharm_GC_C_113
_atom_site_anharm_GC_C_122
_atom_site_anharm_GC_C_123
_atom_site_anharm_GC_C_133
_atom_site_anharm_GC_C_222
_atom_site_anharm_GC_C_223
_atom_site_anharm_GC_C_233
_atom_site_anharm_GC_C_333
Br1 -0.0000029(2) -0.00000189(11) -0.00000143(11) -0.00000096(9) -0.00000089(6)
-0.00000090(9) 0.00000022(12) -0.00000034(7) -0.00000061(6) -0.00000089(10)
Br2 -0.0000032(3) 0.00000325(13) 0.00000149(13) 0.00000138(9) 0.00000117(6)
0.00000064(9) 0.00000024(12) 0.00000064(6) 0.00000055(5) 0.00000037(9)
Br4 0.0000011(2) 0.00000093(10) -0.00000043(11) 0.00000079(7) -0.00000015(5)
-0.00000005(8) 0.00000034(10) 0.00000008(5) -0.00000017(5) 0.00000003(10)

loop_
_atom_site_anharm_GC_D_label
_atom_site_anharm_GC_D_1111
_atom_site_anharm_GC_D_1112
_atom_site_anharm_GC_D_1113
_atom_site_anharm_GC_D_1122
_atom_site_anharm_GC_D_1123
_atom_site_anharm_GC_D_1133
_atom_site_anharm_GC_D_1222
_atom_site_anharm_GC_D_1223
_atom_site_anharm_GC_D_1233
_atom_site_anharm_GC_D_1333
_atom_site_anharm_GC_D_2222
_atom_site_anharm_GC_D_2223
_atom_site_anharm_GC_D_2233
_atom_site_anharm_GC_D_2333
_atom_site_anharm_GC_D_3333
Br1 0.00000009(2) 0.000000053(9) 0.000000014(9) 0.000000030(6) 0.000000010(4)
0.000000013(6) 0.000000030(6) 0.000000007(3) -0.000000000(3) 0.000000006(6)
0.000000038(9) 0.000000017(4) 0.000000007(3) -0.000000003(4) 0.000000002(7)
Br2 0.00000019(3) 0.000000003(11) 0.000000008(12) 0.000000030(6) 0.000000011(4)
0.000000022(7) 0.000000022(6) 0.000000009(3) 0.000000007(3) 0.000000016(5)
0.000000049(9) 0.000000012(4) 0.000000015(3) 0.000000004(3) 0.000000022(7)
Br4 0.00000011(2) 0.000000024(8) 0.000000018(10) 0.000000034(4) -0.000000001(4)
0.000000029(6) 0.000000006(4) 0.000000004(2) 0.000000003(3) 0.000000020(6)
0.000000051(7) -0.000000004(3) 0.000000015(2) 0.000000002(3) 0.000000043(8)


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
C1 S1 1.726(4) . ?
C1 C4 1.376(5) . ?
C1 C7 1.464(5) . ?
O1 C13 1.215(5) . ?
S1 C2 1.723(4) . ?
Br1 C9 1.895(4) . ?
C2 C3 1.390(5) . ?
C2 C13 1.478(5) . ?
O2 C26 1.223(5) . ?
S2 C4 1.738(4) . ?
S2 C6 1.751(4) . ?
Br2 C16 1.882(4) . ?
C3 C4 1.428(5) . ?
C3 C5 1.447(5) . ?
Br4 C29 1.875(5) . ?
C5 C6 1.377(5) . ?
C5 C20 1.491(12) . ?
C5 C20B 1.51(2) . ?
C6 C26 1.490(5) . ?
C7 C8 1.391(5) . ?
C7 C12 1.394(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.370(5) . ?
C9 C10 1.383(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.499(5) . ?
C14 C15 1.389(5) . ?
C14 C19 1.387(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.376(6) . ?
C16 C17 1.370(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(6) . ?
C19 H19 0.9300 . ?
Br3 C22 1.882(9) . ?
C20 C21 1.385(13) . ?
C20 C25 1.403(11) . ?
C21 H21 0.9300 . ?
C21 C22 1.373(14) . ?
C22 C23 1.381(12) . ?
C23 H23 0.9300 . ?
C23 C24 1.386(13) . ?
C24 H24 0.9300 . ?
C24 C25 1.365(14) . ?
C25 H25 0.9300 . ?
Br3B C24B 1.905(19) . ?
C20B C21B 1.34(2) . ?
C20B C25B 1.40(2) . ?
C21B H21B 0.9300 . ?
C21B C22B 1.39(3) . ?
C22B H22B 0.9300 . ?
C22B C23B 1.33(3) . ?
C23B H23B 0.9300 . ?
C23B C24B 1.26(3) . ?
C24B C25B 1.49(3) . ?
C25B H25B 0.9300 . ?
C26 C27 1.488(5) . ?
C27 C28 1.374(6) . ?
C27 C32 1.394(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.380(5) . ?
C29 C30 1.379(6) . ?
C30 H30 0.9300 . ?
C30 C31 1.378(7) . ?
C31 H31 0.9300 . ?
C31 C32 1.376(7) . ?
C32 H32 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C1 S1 108.8(2) . . ?
C7 C1 S1 121.4(3) . . ?
C7 C1 C4 129.8(3) . . ?
C2 S1 C1 94.12(17) . . ?
C3 C2 S1 110.3(3) . . ?
C13 C2 S1 116.1(3) . . ?
C13 C2 C3 133.6(3) . . ?
C6 S2 C4 90.72(17) . . ?
C4 C3 C2 111.6(3) . . ?
C5 C3 C2 136.3(3) . . ?
C5 C3 C4 112.1(3) . . ?
S2 C4 C1 133.2(3) . . ?
C3 C4 C1 115.1(3) . . ?
C3 C4 S2 111.6(3) . . ?
C6 C5 C3 111.1(3) . . ?
C20 C5 C3 127.5(8) . . ?
C20 C5 C6 121.4(8) . . ?
C20B C5 C3 117.9(13) . . ?
C20B C5 C6 129.4(14) . . ?
C5 C6 S2 114.1(3) . . ?
C26 C6 S2 114.1(3) . . ?
C26 C6 C5 131.7(3) . . ?
C8 C7 C1 119.4(3) . . ?
C12 C7 C1 122.3(3) . . ?
C12 C7 C8 118.3(3) . . ?
H8 C8 C7 119.9(2) . . ?
C9 C8 C7 120.1(4) . . ?
C9 C8 H8 119.9(2) . . ?
C8 C9 Br1 118.6(3) . . ?
C10 C9 Br1 119.5(3) . . ?
C10 C9 C8 121.7(4) . . ?
H10 C10 C9 120.8(2) . . ?
C11 C10 C9 118.4(3) . . ?
C11 C10 H10 120.8(2) . . ?
H11 C11 C10 119.7(2) . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 H11 119.7(2) . . ?
C11 C12 C7 120.9(4) . . ?
H12 C12 C7 119.6(2) . . ?
H12 C12 C11 119.6(2) . . ?
C2 C13 O1 120.4(3) . . ?
C14 C13 O1 121.1(3) . . ?
C14 C13 C2 118.4(3) . . ?
C15 C14 C13 118.5(4) . . ?
C19 C14 C13 121.3(3) . . ?
C19 C14 C15 120.2(4) . . ?
H15 C15 C14 120.2(2) . . ?
C16 C15 C14 119.6(4) . . ?
C16 C15 H15 120.2(3) . . ?
C15 C16 Br2 119.4(3) . . ?
C17 C16 Br2 119.9(3) . . ?
C17 C16 C15 120.6(4) . . ?
H17 C17 C16 120.1(3) . . ?
C18 C17 C16 119.8(4) . . ?
C18 C17 H17 120.1(3) . . ?
H18 C18 C17 119.8(3) . . ?
C19 C18 C17 120.3(4) . . ?
C19 C18 H18 119.8(3) . . ?
C18 C19 C14 119.3(4) . . ?
H19 C19 C14 120.3(2) . . ?
H19 C19 C18 120.3(3) . . ?
C21 C20 C5 116.1(8) . . ?
C25 C20 C5 124.5(8) . . ?
C25 C20 C21 119.2(9) . . ?
H21 C21 C20 119.7(6) . . ?
C22 C21 C20 120.5(8) . . ?
C22 C21 H21 119.7(6) . . ?
C21 C22 Br3 119.4(8) . . ?
C23 C22 Br3 119.4(8) . . ?
C23 C22 C21 121.2(8) . . ?
H23 C23 C22 121.2(6) . . ?
C24 C23 C22 117.5(9) . . ?
C24 C23 H23 121.2(5) . . ?
H24 C24 C23 118.5(5) . . ?
C25 C24 C23 123.0(8) . . ?
C25 C24 H24 118.5(5) . . ?
C24 C25 C20 118.6(8) . . ?
H25 C25 C20 120.7(6) . . ?
H25 C25 C24 120.7(5) . . ?
C21B C20B C5 126.1(17) . . ?
C25B C20B C5 112.9(16) . . ?
C25B C20B C21B 121.1(17) . . ?
H21B C21B C20B 119.6(12) . . ?
C22B C21B C20B 120.8(16) . . ?
C22B C21B H21B 119.6(11) . . ?
H22B C22B C21B 120.8(11) . . ?
C23B C22B C21B 118.4(18) . . ?
C23B C22B H22B 120.8(11) . . ?
H23B C23B C22B 117.7(11) . . ?
C24B C23B C22B 125(2) . . ?
C24B C23B H23B 117.7(14) . . ?
C23B C24B Br3B 123.5(18) . . ?
C25B C24B Br3B 116.1(16) . . ?
C25B C24B C23B 120.3(17) . . ?
C24B C25B C20B 114.5(16) . . ?
H25B C25B C20B 122.7(11) . . ?
H25B C25B C24B 122.7(11) . . ?
C6 C26 O2 117.8(4) . . ?
C27 C26 O2 121.2(4) . . ?
C27 C26 C6 121.0(3) . . ?
C28 C27 C26 122.9(4) . . ?
C32 C27 C26 117.0(4) . . ?
C32 C27 C28 120.1(4) . . ?
H28 C28 C27 120.2(2) . . ?
C29 C28 C27 119.6(4) . . ?
C29 C28 H28 120.2(3) . . ?
C28 C29 Br4 120.1(3) . . ?
C30 C29 Br4 119.1(3) . . ?
C30 C29 C28 120.8(4) . . ?
H30 C30 C29 120.4(3) . . ?
C31 C30 C29 119.3(4) . . ?
C31 C30 H30 120.4(3) . . ?
H31 C31 C30 119.6(3) . . ?
C32 C31 C30 120.8(4) . . ?
C32 C31 H31 119.6(3) . . ?
C31 C32 C27 119.3(5) . . ?
H32 C32 C27 120.3(3) . . ?
H32 C32 C31 120.3(3) . . ?

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
C1 C4 C3 C2 1.9(4) . . . . ?
C1 C4 C3 C5 -175.9(3) . . . . ?
C1 C7 C8 C9 -178.8(4) . . . . ?
C1 C7 C12 C11 179.1(4) . . . . ?
O1 C13 C2 S1 -34.8(4) . . . . ?
O1 C13 C2 C3 146.4(4) . . . . ?
O1 C13 C14 C15 -38.9(4) . . . . ?
O1 C13 C14 C19 139.7(4) . . . . ?
S1 C2 C3 C4 -2.9(3) . . . . ?
S1 C2 C3 C5 174.1(2) . . . . ?
S1 C2 C13 C14 141.7(3) . . . . ?
Br1 C9 C8 C7 174.9(3) . . . . ?
Br1 C9 C10 C11 -175.1(3) . . . . ?
C2 C3 C4 S2 -175.7(3) . . . . ?
C2 C3 C5 C6 178.0(5) . . . . ?
C2 C3 C5 C20 -0.4(8) . . . . ?
C2 C3 C5 C20B -14.9(13) . . . . ?
C2 C13 C14 C15 144.6(3) . . . . ?
C2 C13 C14 C19 -36.7(4) . . . . ?
O2 C26 C6 S2 -28.0(4) . . . . ?
O2 C26 C6 C5 148.8(4) . . . . ?
O2 C26 C27 C28 140.7(4) . . . . ?
O2 C26 C27 C32 -39.1(5) . . . . ?
S2 C4 C3 C5 6.6(3) . . . . ?
S2 C6 C5 C3 1.3(3) . . . . ?
S2 C6 C5 C20 179.8(7) . . . . ?
S2 C6 C5 C20B -163.9(12) . . . . ?
S2 C6 C26 C27 151.4(3) . . . . ?
Br2 C16 C15 C14 173.8(3) . . . . ?
Br2 C16 C17 C18 -174.4(3) . . . . ?
C3 C5 C6 C26 -175.5(3) . . . . ?
C3 C5 C20 C21 -61.6(8) . . . . ?
C3 C5 C20 C25 123.3(12) . . . . ?
C3 C5 C20B C21B -50.6(17) . . . . ?
C3 C5 C20B C25B 128.6(19) . . . . ?
Br4 C29 C28 C27 -178.8(3) . . . . ?
Br4 C29 C30 C31 179.9(4) . . . . ?
C5 C6 C26 C27 -31.8(5) . . . . ?
C5 C20 C21 C22 -175.0(11) . . . . ?
C5 C20 C25 C24 175.6(14) . . . . ?
C5 C20B C21B C22B -176(3) . . . . ?
C5 C20B C25B C24B 176.6(19) . . . . ?
C6 C26 C27 C28 -38.7(4) . . . . ?
C6 C26 C27 C32 141.5(4) . . . . ?
C7 C8 C9 C10 -0.7(5) . . . . ?
C7 C12 C11 C10 0.1(5) . . . . ?
C8 C9 C10 C11 0.5(5) . . . . ?
C9 C10 C11 C12 -0.2(5) . . . . ?
C13 C14 C15 C16 179.8(4) . . . . ?
C13 C14 C19 C18 -177.2(4) . . . . ?
C14 C15 C16 C17 -3.1(5) . . . . ?
C14 C19 C18 C17 -2.1(5) . . . . ?
C15 C16 C17 C18 2.5(5) . . . . ?
C16 C17 C18 C19 0.1(5) . . . . ?
Br3 C22 C21 C20 -179.7(12) . . . . ?
Br3 C22 C23 C24 179.3(8) . . . . ?
C20 C21 C22 C23 -1.0(17) . . . . ?
C20 C25 C24 C23 -1.1(19) . . . . ?
C21 C22 C23 C24 0.6(12) . . . . ?
C22 C23 C24 C25 0.5(14) . . . . ?
Br3B C24B C23B C22B 179.9(16) . . . . ?
Br3B C24B C25B C20B -177(2) . . . . ?
C20B C21B C22B C23B -1(3) . . . . ?
C20B C25B C24B C23B -0(3) . . . . ?
C21B C22B C23B C24B -3(3) . . . . ?
C22B C23B C24B C25B 4(3) . . . . ?
C26 C27 C28 C29 178.0(4) . . . . ?
C26 C27 C32 C31 -176.6(4) . . . . ?
C27 C28 C29 C30 -0.4(5) . . . . ?
C27 C32 C31 C30 -2.5(5) . . . . ?
C28 C29 C30 C31 1.5(5) . . . . ?
C29 C30 C31 C32 -0.0(6) . . . . ?


_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 2.085
_oxdiff_exptl_absorpt_empirical_full_min 0.737
loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_id
C5 C20 1 1
C5 C20B 1 1

loop_
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
_restr_equal_distance_class_average
_restr_equal_distance_class_esd
_restr_equal_distance_class_diff_max
1 0.0200 1.5016 0.0107 0.0107

loop_
_restr_U_rigid_atom_site_label_1
_restr_U_rigid_atom_site_label_2
_restr_U_rigid_target_weight_param
_restr_U_rigid_U_parallel
_restr_U_rigid_diff
Br3 C21 0.0100 0.0379 -0.0054
Br3 C22 0.0100 0.0487 -0.0005
Br3 C23 0.0100 0.0709 -0.0032
C20 C21 0.0100 0.0378 -0.0095
C20 C22 0.0100 0.0344 -0.0038
C20 C24 0.0100 0.0294 -0.0072
C20 C25 0.0100 0.0269 -0.0015
C21 C22 0.0100 0.0323 0.0048
C21 C23 0.0100 0.0312 0.0023
C21 C25 0.0100 0.0402 -0.0002
C22 C23 0.0100 0.0498 -0.0032
C22 C24 0.0100 0.0590 -0.0081
C23 C24 0.0100 0.0690 -0.0024
C23 C25 0.0100 0.0513 -0.0089
C24 C25 0.0100 0.0427 -0.0025
Br3B C23B 0.0100 0.1035 0.0151
Br3B C24B 0.0100 0.0557 0.0088
Br3B C25B 0.0100 0.0315 -0.0029
C20B C21B 0.0100 0.0407 0.0023
C20B C22B 0.0100 0.0438 -0.0030
C20B C24B 0.0100 0.0297 -0.0022
C20B C25B 0.0100 0.0297 -0.0046
C21B C22B 0.0100 0.0365 -0.0049
C21B C23B 0.0100 0.0403 -0.0034
C21B C25B 0.0100 0.0431 0.0010
C22B C23B 0.0100 0.0753 -0.0018
C22B C24B 0.0100 0.0799 0.0009
C23B C24B 0.0100 0.0927 0.0043
C23B C25B 0.0100 0.0595 0.0032
C24B C25B 0.0100 0.0459 -0.0054

loop_
_restr_U_similar_atom_site_label_1
_restr_U_similar_atom_site_label_2
_restr_U_similar_weight_param
Br3 C22 0.0800
Br3 C22B 0.0800
Br3 C23B 0.0800
C20 C21 0.0400
C20 C25 0.0400
C20 C20B 0.0400
C20 C21B 0.0400
C20 C25B 0.0400
C21 C22 0.0400
C21 C20B 0.0400
C21 C21B 0.0400
C21 C22B 0.0400
C21 C25B 0.0400
C22 C23 0.0400
C22 C21B 0.0400
C22 C22B 0.0400
C22 C23B 0.0400
C22 C24B 0.0400
C23 C24 0.0400
C23 Br3B 0.0800
C23 C22B 0.0400
C23 C23B 0.0400
C23 C24B 0.0400
C24 C25 0.0400
C24 Br3B 0.0800
C24 C23B 0.0400
C24 C24B 0.0400
C24 C25B 0.0400
C25 C20B 0.0400
C25 C24B 0.0400
C25 C25B 0.0400
Br3B C24B 0.0800
C20B C21B 0.0400
C20B C25B 0.0400
C21B C22B 0.0400
C22B C23B 0.0400
C23B C24B 0.0400
C24B C25B 0.0400




