# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_NTT030F1F2
_database_code_depnum_ccdc_archive 'CCDC 2163449'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3

_chemical_name_systematic        
;
'ethyl 5-benzoyl-2-phenyl-4-(4-(trifluoromethyl)phenyl)thiophene-3-carboxylate'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H19 F3 O3 S'
_chemical_formula_sum            'C27 H19 F3 O3 S'
_chemical_formula_weight         480.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   9.6201(4)
_cell_length_b                   11.1658(4)
_cell_length_c                   11.4664(4)
_cell_angle_alpha                95.279(3)
_cell_angle_beta                 95.489(3)
_cell_angle_gamma                106.999(4)
_cell_volume                     1163.11(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    12322
_cell_measurement_theta_min      3.0610
_cell_measurement_theta_max      30.5810

_exptl_crystal_description       tab
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.031
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 1 5 0.0232
4 -1 -5 0.0082
3 -2 5 0.0619
-4 3 -5 0.1087
0 -1 0 0.0298
0 5 1 0.0285
-2 5 -2 0.0542
4 1 5 0.0549
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_min  0.716
_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_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_detector                 'Dectris PILATUS3 R 200K-A area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'Hybrid Photon Counting area detector'

_diffrn_measurement_device       'kappa gonio four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'

_diffrn_radiation_collimation    
'Rigaku Integrated Confocal MaxFlux double bounce multi-layer mirror optics'
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          x-ray

_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku micromax 003'
_diffrn_reflns_number            34665
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.464
_diffrn_reflns_theta_max         27.877
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5554
_reflns_number_gt                4588
_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 1.171.41.108a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.108a (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)+(0.0506P)²+0.2611P] 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         5554
_refine_ls_number_parameters     336
_refine_ls_number_restraints     105
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.1006
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.062
_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
F1 F 0.10537(16) 0.31831(15) -0.07491(16) 0.1128(7) Uani 0.950(2) 1 d D . P A 1
F2 F 0.08128(14) 0.13726(14) -0.02346(11) 0.0955(5) Uani 0.950(2) 1 d D . P A 1
F3 F 0.21504(13) 0.20038(14) -0.15457(9) 0.0841(4) Uani 0.950(2) 1 d D . P A 1
F4 F 0.0525(18) 0.2345(14) -0.021(2) 0.096(4) Uani 0.050(2) 1 d D U P A 1
F5 F 0.166(3) 0.1226(12) -0.091(2) 0.111(8) Uani 0.050(2) 1 d D . P A 1
F6 F 0.185(3) 0.2971(18) -0.1423(14) 0.096(4) Uani 0.050(2) 1 d D U P A 1
O1 O 0.46438(13) 0.65345(13) 0.47546(9) 0.0659(3) Uani 1 1 d . . . . .
S1 S 0.91641(3) 0.61557(3) 0.41453(3) 0.04551(11) Uani 1 1 d . . . . .
C2 C 0.78112(14) 0.68336(12) 0.43727(11) 0.0385(3) Uani 1 1 d . . . . .
O2 O 0.44745(10) 0.66220(10) 0.28137(8) 0.0449(2) Uani 1 1 d . . . . .
C3 C 0.65060(13) 0.61338(12) 0.37198(10) 0.0358(3) Uani 1 1 d . . . . .
O3 O 0.99075(12) 0.42167(12) 0.26456(13) 0.0698(3) Uani 1 1 d . . . . .
C4 C 0.65903(13) 0.50405(12) 0.30208(10) 0.0351(2) Uani 1 1 d . . . . .
C5 C 0.79766(13) 0.49141(12) 0.31957(11) 0.0393(3) Uani 1 1 d . . . . .
C6 C 0.81566(14) 0.80495(12) 0.51288(11) 0.0405(3) Uani 1 1 d . . . . .
C7 C 0.90733(16) 0.82867(14) 0.61869(13) 0.0501(3) Uani 1 1 d . . . . .
H7 H 0.947159 0.767149 0.642975 0.060 Uiso 1 1 calc R U . . .
C8 C 0.9398(2) 0.94395(16) 0.68843(15) 0.0641(4) Uani 1 1 d . . . . .
H8 H 1.000731 0.959111 0.759700 0.077 Uiso 1 1 calc R U . . .
C9 C 0.8830(2) 1.03544(16) 0.65326(17) 0.0671(5) Uani 1 1 d . . . . .
H9 H 0.904763 1.112415 0.700655 0.080 Uiso 1 1 calc R U . . .
C10 C 0.7936(2) 1.01359(16) 0.54782(17) 0.0669(5) Uani 1 1 d . . . . .
H10 H 0.755558 1.076203 0.523656 0.080 Uiso 1 1 calc R U . . .
C11 C 0.75974(19) 0.89901(15) 0.47737(14) 0.0558(4) Uani 1 1 d . . . . .
H11 H 0.699317 0.884937 0.405954 0.067 Uiso 1 1 calc R U . . .
C12 C 0.51230(14) 0.64538(13) 0.38377(11) 0.0396(3) Uani 1 1 d . . . . .
C13 C 0.30241(17) 0.6776(2) 0.28479(15) 0.0631(4) Uani 1 1 d . . . . .
H13A H 0.310433 0.758553 0.328275 0.076 Uiso 1 1 calc R U . . .
H13B H 0.242022 0.611513 0.323754 0.076 Uiso 1 1 calc R U . . .
C14 C 0.2358(2) 0.6703(3) 0.16178(19) 0.0864(7) Uani 1 1 d . . . . .
H14A H 0.229001 0.590070 0.119421 0.130 Uiso 1 1 calc R U . . .
H14B H 0.295684 0.736717 0.124395 0.130 Uiso 1 1 calc R U . . .
H14C H 0.139595 0.679282 0.161582 0.130 Uiso 1 1 calc R U . . .
C15 C 0.53616(13) 0.42329(11) 0.21427(10) 0.0345(2) Uani 1 1 d . . . . .
C16 C 0.39494(15) 0.37755(14) 0.24374(12) 0.0442(3) Uani 1 1 d . . . . .
H16 H 0.378117 0.389117 0.321905 0.053 Uiso 1 1 calc R U . . .
C17 C 0.27974(15) 0.31514(14) 0.15760(13) 0.0478(3) Uani 1 1 d . . . . .
H17 H 0.185114 0.286572 0.177382 0.072 Uiso 1 1 calc R U . . .
C18 C 0.30511(14) 0.29501(12) 0.04147(11) 0.0403(3) Uani 1 1 d . . . . .
C19 C 0.44539(14) 0.33535(12) 0.01161(11) 0.0399(3) Uani 1 1 d . . . . .
H19 H 0.462660 0.319320 -0.065853 0.048 Uiso 1 1 calc R U . . .
C20 C 0.56020(13) 0.39993(12) 0.09808(11) 0.0371(3) Uani 1 1 d . . . . .
H20 H 0.654747 0.428059 0.078046 0.044 Uiso 1 1 calc R U . . .
C21 C 0.17801(17) 0.23736(16) -0.05214(14) 0.0567(4) Uani 1 1 d D . . . .
C22 C 0.85939(15) 0.39392(14) 0.27135(12) 0.0444(3) Uani 1 1 d . . . . .
C23 C 0.76336(15) 0.26266(13) 0.23539(12) 0.0444(3) Uani 1 1 d . . . . .
C24 C 0.65037(18) 0.20687(15) 0.29718(15) 0.0566(4) Uani 1 1 d . . . . .
H24 H 0.631247 0.252095 0.362745 0.068 Uiso 1 1 calc R U . . .
C25 C 0.5656(2) 0.08312(19) 0.2609(2) 0.0831(6) Uani 1 1 d . . . . .
H25 H 0.490293 0.044617 0.302941 0.100 Uiso 1 1 calc R U . . .
C26 C 0.5927(3) 0.0173(2) 0.1633(3) 0.0955(8) Uani 1 1 d . . . . .
H26 H 0.534430 -0.065344 0.138783 0.115 Uiso 1 1 calc R U . . .
C28 C 0.79079(19) 0.19386(17) 0.13770(15) 0.0596(4) Uani 1 1 d . . . . .
H28 H 0.867922 0.230353 0.096549 0.071 Uiso 1 1 calc R U . . .
C27 C 0.7037(3) 0.0716(2) 0.1019(2) 0.0835(6) Uani 1 1 d . . . . .
H27 H 0.720804 0.026124 0.035568 0.100 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
F1 F4 1.186(12) . ?
F1 F6 1.197(12) . ?
F1 C21 1.323(2) . ?
F2 F4 1.195(12) . ?
F2 F5 1.208(13) . ?
F2 C21 1.320(2) . ?
F3 F6 1.195(12) . ?
F3 F5 1.205(13) . ?
F3 C21 1.324(2) . ?
F4 C21 1.284(13) . ?
F5 C21 1.285(13) . ?
F6 C21 1.277(13) . ?
O1 C12 1.1939(16) . ?
S1 C2 1.7145(13) . ?
S1 C5 1.7235(13) . ?
C2 C3 1.3735(17) . ?
C2 C6 1.4730(18) . ?
O2 C12 1.3312(15) . ?
O2 C13 1.4585(16) . ?
C3 C4 1.4246(17) . ?
C3 C12 1.4898(17) . ?
O3 C22 1.2220(17) . ?
C4 C5 1.3794(17) . ?
C4 C15 1.4853(16) . ?
C5 C22 1.4742(18) . ?
C6 C7 1.3854(19) . ?
C6 C11 1.388(2) . ?
C7 C8 1.386(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.366(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.373(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C13 C14 1.477(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.3881(17) . ?
C15 C16 1.3909(18) . ?
C16 C17 1.3790(19) . ?
C16 H16 0.9300 . ?
C17 C18 1.3865(19) . ?
C17 H17 0.9300 . ?
C18 C19 1.3793(19) . ?
C18 C21 1.4910(18) . ?
C19 C20 1.3843(17) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C22 C23 1.482(2) . ?
C23 C24 1.380(2) . ?
C23 C28 1.390(2) . ?
C24 C25 1.385(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.370(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.359(4) . ?
C26 H26 0.9300 . ?
C28 C27 1.377(3) . ?
C28 H28 0.9300 . ?
C27 H27 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
F4 F1 F6 115.4(12) . . ?
F4 F1 C21 61.3(6) . . ?
F6 F1 C21 60.7(6) . . ?
F4 F2 F5 116.4(12) . . ?
F4 F2 C21 61.2(6) . . ?
F5 F2 C21 60.9(6) . . ?
F6 F3 F5 117.1(11) . . ?
F6 F3 C21 60.7(6) . . ?
F5 F3 C21 60.8(6) . . ?
F1 F4 F2 125.0(13) . . ?
F1 F4 C21 64.6(7) . . ?
F2 F4 C21 64.2(7) . . ?
F3 F5 F2 121.8(15) . . ?
F3 F5 C21 64.2(6) . . ?
F2 F5 C21 63.8(6) . . ?
F3 F6 F1 124.0(14) . . ?
F3 F6 C21 64.7(7) . . ?
F1 F6 C21 64.6(7) . . ?
C2 S1 C5 92.31(6) . . ?
C3 C2 C6 128.85(12) . . ?
C3 C2 S1 110.82(9) . . ?
C6 C2 S1 120.22(9) . . ?
C12 O2 C13 115.25(11) . . ?
C2 C3 C4 113.82(11) . . ?
C2 C3 C12 121.62(11) . . ?
C4 C3 C12 124.34(11) . . ?
C5 C4 C3 111.24(11) . . ?
C5 C4 C15 125.63(11) . . ?
C3 C4 C15 122.89(10) . . ?
C4 C5 C22 131.81(12) . . ?
C4 C5 S1 111.74(9) . . ?
C22 C5 S1 116.45(9) . . ?
C7 C6 C11 118.93(13) . . ?
C7 C6 C2 120.78(12) . . ?
C11 C6 C2 120.27(12) . . ?
C6 C7 C8 120.12(15) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 120.49(15) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.90(15) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C11 120.36(16) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C6 120.20(15) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
O1 C12 O2 123.86(12) . . ?
O1 C12 C3 123.24(12) . . ?
O2 C12 C3 112.89(10) . . ?
O2 C13 C14 107.83(13) . . ?
O2 C13 H13A 110.1 . . ?
C14 C13 H13A 110.1 . . ?
O2 C13 H13B 110.1 . . ?
C14 C13 H13B 110.1 . . ?
H13A C13 H13B 108.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 118.98(11) . . ?
C20 C15 C4 119.37(11) . . ?
C16 C15 C4 121.50(11) . . ?
C17 C16 C15 120.32(12) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 119.94(12) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 120.43(12) . . ?
C19 C18 C21 120.21(13) . . ?
C17 C18 C21 119.23(13) . . ?
C18 C19 C20 119.34(12) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C19 C20 C15 120.91(11) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
F6 C21 F4 103.7(11) . . ?
F6 C21 F5 106.1(12) . . ?
F4 C21 F5 105.3(12) . . ?
F6 C21 F2 133.9(11) . . ?
F4 C21 F2 54.6(5) . . ?
F5 C21 F2 55.3(6) . . ?
F6 C21 F1 54.8(6) . . ?
F4 C21 F1 54.1(5) . . ?
F5 C21 F1 135.6(14) . . ?
F2 C21 F1 106.08(16) . . ?
F6 C21 F3 54.6(6) . . ?
F4 C21 F3 131.1(11) . . ?
F5 C21 F3 55.0(6) . . ?
F2 C21 F3 105.82(14) . . ?
F1 C21 F3 105.75(16) . . ?
F6 C21 C18 112.7(11) . . ?
F4 C21 C18 115.0(11) . . ?
F5 C21 C18 113.1(14) . . ?
F2 C21 C18 113.41(14) . . ?
F1 C21 C18 111.27(13) . . ?
F3 C21 C18 113.88(13) . . ?
O3 C22 C5 119.37(13) . . ?
O3 C22 C23 120.54(13) . . ?
C5 C22 C23 120.06(12) . . ?
C24 C23 C28 119.58(15) . . ?
C24 C23 C22 121.97(13) . . ?
C28 C23 C22 118.44(14) . . ?
C23 C24 C25 119.57(17) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 120.1(2) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C27 C26 C25 120.7(2) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C27 C28 C23 119.96(19) . . ?
C27 C28 H28 120.0 . . ?
C23 C28 H28 120.0 . . ?
C26 C27 C28 120.07(19) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F6 F1 F4 F2 5(3) . . . . ?
C21 F1 F4 F2 -23.1(16) . . . . ?
F6 F1 F4 C21 28.4(17) . . . . ?
F5 F2 F4 F1 -4(3) . . . . ?
C21 F2 F4 F1 23.2(16) . . . . ?
F5 F2 F4 C21 -27(2) . . . . ?
F6 F3 F5 F2 5(4) . . . . ?
C21 F3 F5 F2 28.8(17) . . . . ?
F6 F3 F5 C21 -24(2) . . . . ?
F4 F2 F5 F3 -2(4) . . . . ?
C21 F2 F5 F3 -28.9(18) . . . . ?
F4 F2 F5 C21 27(2) . . . . ?
F5 F3 F6 F1 -3(3) . . . . ?
C21 F3 F6 F1 -27.0(15) . . . . ?
F5 F3 F6 C21 24(2) . . . . ?
F4 F1 F6 F3 -2(3) . . . . ?
C21 F1 F6 F3 27.0(15) . . . . ?
F4 F1 F6 C21 -28.6(17) . . . . ?
C5 S1 C2 C3 -1.11(10) . . . . ?
C5 S1 C2 C6 -177.58(11) . . . . ?
C6 C2 C3 C4 175.77(12) . . . . ?
S1 C2 C3 C4 -0.32(14) . . . . ?
C6 C2 C3 C12 -9.4(2) . . . . ?
S1 C2 C3 C12 174.49(10) . . . . ?
C2 C3 C4 C5 2.04(16) . . . . ?
C12 C3 C4 C5 -172.60(12) . . . . ?
C2 C3 C4 C15 -172.60(11) . . . . ?
C12 C3 C4 C15 12.76(19) . . . . ?
C3 C4 C5 C22 177.98(13) . . . . ?
C15 C4 C5 C22 -7.6(2) . . . . ?
C3 C4 C5 S1 -2.82(14) . . . . ?
C15 C4 C5 S1 171.64(10) . . . . ?
C2 S1 C5 C4 2.29(11) . . . . ?
C2 S1 C5 C22 -178.38(11) . . . . ?
C3 C2 C6 C7 141.67(15) . . . . ?
S1 C2 C6 C7 -42.57(17) . . . . ?
C3 C2 C6 C11 -40.1(2) . . . . ?
S1 C2 C6 C11 135.66(13) . . . . ?
C11 C6 C7 C8 1.2(2) . . . . ?
C2 C6 C7 C8 179.46(15) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
C9 C10 C11 C6 0.2(3) . . . . ?
C7 C6 C11 C10 -1.0(2) . . . . ?
C2 C6 C11 C10 -179.29(15) . . . . ?
C13 O2 C12 O1 -6.7(2) . . . . ?
C13 O2 C12 C3 172.41(13) . . . . ?
C2 C3 C12 O1 -56.4(2) . . . . ?
C4 C3 C12 O1 117.89(16) . . . . ?
C2 C3 C12 O2 124.48(13) . . . . ?
C4 C3 C12 O2 -61.27(17) . . . . ?
C12 O2 C13 C14 -169.24(16) . . . . ?
C5 C4 C15 C20 -49.03(18) . . . . ?
C3 C4 C15 C20 124.82(13) . . . . ?
C5 C4 C15 C16 135.49(14) . . . . ?
C3 C4 C15 C16 -50.66(18) . . . . ?
C20 C15 C16 C17 -3.0(2) . . . . ?
C4 C15 C16 C17 172.50(13) . . . . ?
C15 C16 C17 C18 1.6(2) . . . . ?
C16 C17 C18 C19 1.0(2) . . . . ?
C16 C17 C18 C21 -174.77(14) . . . . ?
C17 C18 C19 C20 -2.1(2) . . . . ?
C21 C18 C19 C20 173.59(13) . . . . ?
C18 C19 C20 C15 0.70(19) . . . . ?
C16 C15 C20 C19 1.84(19) . . . . ?
C4 C15 C20 C19 -173.75(11) . . . . ?
F3 F6 C21 F4 -131.1(11) . . . . ?
F1 F6 C21 F4 24.3(15) . . . . ?
F3 F6 C21 F5 -20.4(17) . . . . ?
F1 F6 C21 F5 135.0(13) . . . . ?
F3 F6 C21 F2 -77.4(10) . . . . ?
F1 F6 C21 F2 78.0(10) . . . . ?
F3 F6 C21 F1 -155.3(16) . . . . ?
F1 F6 C21 F3 155.3(16) . . . . ?
F3 F6 C21 C18 103.9(8) . . . . ?
F1 F6 C21 C18 -100.7(8) . . . . ?
F1 F4 C21 F6 -24.5(15) . . . . ?
F2 F4 C21 F6 134.6(11) . . . . ?
F1 F4 C21 F5 -135.8(13) . . . . ?
F2 F4 C21 F5 23.3(17) . . . . ?
F1 F4 C21 F2 -159.1(16) . . . . ?
F2 F4 C21 F1 159.1(16) . . . . ?
F1 F4 C21 F3 -79.2(10) . . . . ?
F2 F4 C21 F3 79.9(10) . . . . ?
F1 F4 C21 C18 99.0(8) . . . . ?
F2 F4 C21 C18 -101.9(8) . . . . ?
F3 F5 C21 F6 20.3(18) . . . . ?
F2 F5 C21 F6 -132.6(12) . . . . ?
F3 F5 C21 F4 129.8(12) . . . . ?
F2 F5 C21 F4 -23.1(17) . . . . ?
F3 F5 C21 F2 152.9(19) . . . . ?
F3 F5 C21 F1 76.0(12) . . . . ?
F2 F5 C21 F1 -76.9(12) . . . . ?
F2 F5 C21 F3 -152.9(19) . . . . ?
F3 F5 C21 C18 -103.8(10) . . . . ?
F2 F5 C21 C18 103.3(10) . . . . ?
F4 F2 C21 F6 -73.8(15) . . . . ?
F5 F2 C21 F6 78.6(18) . . . . ?
F5 F2 C21 F4 152(2) . . . . ?
F4 F2 C21 F5 -152(2) . . . . ?
F4 F2 C21 F1 -17.5(13) . . . . ?
F5 F2 C21 F1 134.9(17) . . . . ?
F4 F2 C21 F3 -129.6(13) . . . . ?
F5 F2 C21 F3 22.8(17) . . . . ?
F4 F2 C21 C18 104.9(13) . . . . ?
F5 F2 C21 C18 -102.7(17) . . . . ?
F4 F1 C21 F6 150(2) . . . . ?
F6 F1 C21 F4 -150(2) . . . . ?
F4 F1 C21 F5 74.1(15) . . . . ?
F6 F1 C21 F5 -76.4(16) . . . . ?
F4 F1 C21 F2 17.6(14) . . . . ?
F6 F1 C21 F2 -132.8(14) . . . . ?
F4 F1 C21 F3 129.7(13) . . . . ?
F6 F1 C21 F3 -20.7(14) . . . . ?
F4 F1 C21 C18 -106.1(14) . . . . ?
F6 F1 C21 C18 103.4(14) . . . . ?
F5 F3 C21 F6 -156(2) . . . . ?
F6 F3 C21 F4 76.5(15) . . . . ?
F5 F3 C21 F4 -79.4(18) . . . . ?
F6 F3 C21 F5 156(2) . . . . ?
F6 F3 C21 F2 133.0(14) . . . . ?
F5 F3 C21 F2 -22.9(17) . . . . ?
F6 F3 C21 F1 20.7(14) . . . . ?
F5 F3 C21 F1 -135.2(17) . . . . ?
F6 F3 C21 C18 -101.8(14) . . . . ?
F5 F3 C21 C18 102.3(17) . . . . ?
C19 C18 C21 F6 -43.4(6) . . . . ?
C17 C18 C21 F6 132.3(6) . . . . ?
C19 C18 C21 F4 -162.0(6) . . . . ?
C17 C18 C21 F4 13.7(6) . . . . ?
C19 C18 C21 F5 77.0(6) . . . . ?
C17 C18 C21 F5 -107.3(6) . . . . ?
C19 C18 C21 F2 137.62(16) . . . . ?
C17 C18 C21 F2 -46.6(2) . . . . ?
C19 C18 C21 F1 -102.88(18) . . . . ?
C17 C18 C21 F1 72.9(2) . . . . ?
C19 C18 C21 F3 16.5(2) . . . . ?
C17 C18 C21 F3 -167.71(15) . . . . ?
C4 C5 C22 O3 154.11(16) . . . . ?
S1 C5 C22 O3 -25.05(18) . . . . ?
C4 C5 C22 C23 -27.9(2) . . . . ?
S1 C5 C22 C23 152.89(11) . . . . ?
O3 C22 C23 C24 141.03(16) . . . . ?
C5 C22 C23 C24 -36.9(2) . . . . ?
O3 C22 C23 C28 -37.7(2) . . . . ?
C5 C22 C23 C28 144.36(13) . . . . ?
C28 C23 C24 C25 -0.1(2) . . . . ?
C22 C23 C24 C25 -178.83(16) . . . . ?
C23 C24 C25 C26 -1.0(3) . . . . ?
C24 C25 C26 C27 0.9(4) . . . . ?
C24 C23 C28 C27 1.2(2) . . . . ?
C22 C23 C28 C27 180.00(15) . . . . ?
C25 C26 C27 C28 0.2(4) . . . . ?
C23 C28 C27 C26 -1.3(3) . . . . ?

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
C14 H14C F1 0.96 2.48 3.380(2) 156.7 2_565 yes

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.044




_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_BN1186
_database_code_depnum_ccdc_archive 'CCDC 2163444'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
;'5-benzoyl-2,4-diphenylthiophene-3-carbonitrile'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H15 N O S'
_chemical_formula_sum            'C24 H15 N O S'
_chemical_formula_weight         365.43

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   7.2549(3)
_cell_length_b                   14.6152(5)
_cell_length_c                   34.7562(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3685.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10866
_cell_measurement_theta_min      2.7890
_cell_measurement_theta_max      28.5780

_exptl_crystal_description       stick
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.042
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 -1 0.0439
0 -1 -5 0.0531
1 2 5 0.0444
3 1 -5 0.0387
0 0 1 0.0152
0 0 -1 0.0271
-1 2 5 0.0635
0 -2 -5 0.0862
0 1 -5 0.0455
-1 -2 5 0.0637
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_min  0.562
_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 (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω-scan
_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            17694
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.787
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_full        25.242
_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             3374
_reflns_number_gt                3053
_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 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_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)+(0.0774P)²+1.8560P] 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         3371
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1547
_refine_ls_wR_factor_gt          0.1521
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.164
_refine_ls_shift/su_max          0.001
_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 0.60977(8) 0.60732(4) 0.46312(2) 0.0381(2) Uani 1 1 d . . . . .
N1 N 0.3704(4) 0.90362(15) 0.40630(7) 0.0637(7) Uani 1 1 d . . . . .
O1 O 0.6236(3) 0.43770(12) 0.42105(5) 0.0622(6) Uani 1 1 d . . . . .
C2 C 0.5525(3) 0.72059(15) 0.46216(6) 0.0354(5) Uani 1 1 d . . . . .
C3 C 0.5033(3) 0.74691(14) 0.42522(6) 0.0362(5) Uani 1 1 d . . . . .
C4 C 0.5135(3) 0.67500(14) 0.39760(6) 0.0350(5) Uani 1 1 d . . . . .
C7 C 0.5225(3) 0.73442(17) 0.53304(6) 0.0423(5) Uani 1 1 d . . . . .
H7 H 0.492853 0.672564 0.534160 0.051 Uiso 1 1 calc R U . . .
C6 C 0.5595(3) 0.77531(14) 0.49775(6) 0.0351(5) Uani 1 1 d . . . . .
C5 C 0.5726(3) 0.59432(14) 0.41440(6) 0.0359(5) Uani 1 1 d . . . . .
C8 C 0.5297(4) 0.78581(18) 0.56658(6) 0.0470(6) Uani 1 1 d . . . . .
H8 H 0.503805 0.758419 0.590113 0.056 Uiso 1 1 calc R U . . .
C9 C 0.5752(4) 0.87743(19) 0.56512(7) 0.0481(6) Uani 1 1 d . . . . .
H9 H 0.578571 0.911825 0.587622 0.058 Uiso 1 1 calc R U . . .
C10 C 0.6157(3) 0.91795(18) 0.53032(7) 0.0436(6) Uani 1 1 d . . . . .
H10 H 0.648670 0.979412 0.529486 0.052 Uiso 1 1 calc R U . . .
C11 C 0.6075(3) 0.86765(16) 0.49656(7) 0.0398(5) Uani 1 1 d . . . . .
H11 H 0.634099 0.895445 0.473141 0.048 Uiso 1 1 calc R U . . .
C12 C 0.4320(4) 0.83533(16) 0.41550(6) 0.0436(6) Uani 1 1 d . . . . .
C13 C 0.4542(3) 0.68859(15) 0.35714(6) 0.0385(5) Uani 1 1 d . . . . .
C14 C 0.3211(4) 0.63305(17) 0.34040(7) 0.0450(5) Uani 1 1 d . . . . .
H14 H 0.266586 0.586401 0.354605 0.054 Uiso 1 1 calc R U . . .
C15 C 0.2697(4) 0.6474(2) 0.30241(8) 0.0594(7) Uani 1 1 d . . . . .
H15 H 0.180734 0.610072 0.291223 0.071 Uiso 1 1 calc R U . . .
C16 C 0.3492(5) 0.7164(2) 0.28116(8) 0.0648(8) Uani 1 1 d . . . . .
H16 H 0.314736 0.725405 0.255663 0.078 Uiso 1 1 calc R U . . .
C17 C 0.4785(5) 0.7714(2) 0.29766(8) 0.0621(8) Uani 1 1 d . . . . .
H17 H 0.531682 0.818256 0.283368 0.075 Uiso 1 1 calc R U . . .
C18 C 0.5314(4) 0.75820(17) 0.33540(7) 0.0492(6) Uani 1 1 d . . . . .
H18 H 0.619530 0.796374 0.346330 0.059 Uiso 1 1 calc R U . . .
C19 C 0.6077(3) 0.50225(15) 0.39897(7) 0.0407(5) Uani 1 1 d . . . . .
C20 C 0.6270(3) 0.48659(15) 0.35664(7) 0.0401(5) Uani 1 1 d . . . . .
C21 C 0.5270(4) 0.41603(16) 0.33998(8) 0.0518(6) Uani 1 1 d . . . . .
H21 H 0.449918 0.379805 0.354978 0.062 Uiso 1 1 calc R U . . .
C22 C 0.5428(5) 0.3999(2) 0.30087(9) 0.0639(8) Uani 1 1 d . . . . .
H22 H 0.474398 0.353446 0.289480 0.077 Uiso 1 1 calc R U . . .
C23 C 0.6587(5) 0.4521(2) 0.27891(8) 0.0631(8) Uani 1 1 d . . . . .
H23 H 0.668241 0.441093 0.252629 0.076 Uiso 1 1 calc R U . . .
C24 C 0.7610(4) 0.5208(2) 0.29544(8) 0.0587(7) Uani 1 1 d . . . . .
H24 H 0.841435 0.555175 0.280428 0.070 Uiso 1 1 calc R U . . .
C25 C 0.7447(4) 0.53889(17) 0.33438(7) 0.0477(6) Uani 1 1 d . . . . .
H25 H 0.812552 0.585954 0.345506 0.057 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 C2 1.707(2) . ?
S1 C5 1.725(2) . ?
N1 C12 1.139(3) . ?
O1 C19 1.221(3) . ?
C2 C3 1.387(3) . ?
C2 C6 1.474(3) . ?
C3 C4 1.425(3) . ?
C3 C12 1.433(3) . ?
C4 C5 1.384(3) . ?
C4 C13 1.484(3) . ?
C7 C8 1.388(3) . ?
C7 C6 1.390(3) . ?
C7 H7 0.9300 . ?
C6 C11 1.395(3) . ?
C5 C19 1.471(3) . ?
C8 C9 1.380(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C13 C18 1.385(3) . ?
C13 C14 1.389(3) . ?
C14 C15 1.388(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.362(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.495(3) . ?
C20 C25 1.383(3) . ?
C20 C21 1.388(3) . ?
C21 C22 1.384(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.368(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.374(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.384(3) . ?
C24 H24 0.9300 . ?
C25 H25 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
C2 S1 C5 92.84(10) . . ?
C3 C2 C6 129.4(2) . . ?
C3 C2 S1 110.46(16) . . ?
C6 C2 S1 120.10(16) . . ?
C2 C3 C4 113.93(19) . . ?
C2 C3 C12 124.2(2) . . ?
C4 C3 C12 121.66(19) . . ?
C5 C4 C3 111.11(19) . . ?
C5 C4 C13 127.13(19) . . ?
C3 C4 C13 121.64(19) . . ?
C8 C7 C6 120.1(2) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C6 C11 119.4(2) . . ?
C7 C6 C2 120.0(2) . . ?
C11 C6 C2 120.58(19) . . ?
C4 C5 C19 132.8(2) . . ?
C4 C5 S1 111.64(16) . . ?
C19 C5 S1 115.56(16) . . ?
C9 C8 C7 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.4(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C6 119.9(2) . . ?
C10 C11 H11 120.0 . . ?
C6 C11 H11 120.0 . . ?
N1 C12 C3 176.5(3) . . ?
C18 C13 C14 118.8(2) . . ?
C18 C13 C4 119.9(2) . . ?
C14 C13 C4 121.3(2) . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 119.7(2) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 120.6(3) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
O1 C19 C5 119.6(2) . . ?
O1 C19 C20 119.4(2) . . ?
C5 C19 C20 120.99(19) . . ?
C25 C20 C21 120.0(2) . . ?
C25 C20 C19 121.6(2) . . ?
C21 C20 C19 118.4(2) . . ?
C22 C21 C20 119.5(3) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C23 C22 C21 120.3(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.4(3) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C25 120.1(3) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C20 C25 C24 119.6(2) . . ?
C20 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?

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
C5 S1 C2 C3 0.89(18) . . . . ?
C5 S1 C2 C6 -179.27(18) . . . . ?
C6 C2 C3 C4 179.8(2) . . . . ?
S1 C2 C3 C4 -0.4(3) . . . . ?
C6 C2 C3 C12 -5.8(4) . . . . ?
S1 C2 C3 C12 174.02(19) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C12 C3 C4 C5 -175.1(2) . . . . ?
C2 C3 C4 C13 175.8(2) . . . . ?
C12 C3 C4 C13 1.3(3) . . . . ?
C8 C7 C6 C11 1.4(4) . . . . ?
C8 C7 C6 C2 179.8(2) . . . . ?
C3 C2 C6 C7 148.2(2) . . . . ?
S1 C2 C6 C7 -31.6(3) . . . . ?
C3 C2 C6 C11 -33.4(4) . . . . ?
S1 C2 C6 C11 146.77(19) . . . . ?
C3 C4 C5 C19 -179.2(2) . . . . ?
C13 C4 C5 C19 4.8(4) . . . . ?
C3 C4 C5 S1 1.1(2) . . . . ?
C13 C4 C5 S1 -174.95(19) . . . . ?
C2 S1 C5 C4 -1.18(18) . . . . ?
C2 S1 C5 C19 179.06(18) . . . . ?
C6 C7 C8 C9 -0.6(4) . . . . ?
C7 C8 C9 C10 -0.7(4) . . . . ?
C8 C9 C10 C11 1.3(4) . . . . ?
C9 C10 C11 C6 -0.5(3) . . . . ?
C7 C6 C11 C10 -0.8(3) . . . . ?
C2 C6 C11 C10 -179.2(2) . . . . ?
C5 C4 C13 C18 -128.5(3) . . . . ?
C3 C4 C13 C18 55.8(3) . . . . ?
C5 C4 C13 C14 51.9(3) . . . . ?
C3 C4 C13 C14 -123.8(2) . . . . ?
C18 C13 C14 C15 0.7(4) . . . . ?
C4 C13 C14 C15 -179.7(2) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C14 C15 C16 C17 -0.4(5) . . . . ?
C15 C16 C17 C18 0.4(5) . . . . ?
C16 C17 C18 C13 0.2(5) . . . . ?
C14 C13 C18 C17 -0.8(4) . . . . ?
C4 C13 C18 C17 179.6(2) . . . . ?
C4 C5 C19 O1 -165.2(3) . . . . ?
S1 C5 C19 O1 14.5(3) . . . . ?
C4 C5 C19 C20 15.7(4) . . . . ?
S1 C5 C19 C20 -164.63(17) . . . . ?
O1 C19 C20 C25 -128.6(3) . . . . ?
C5 C19 C20 C25 50.5(3) . . . . ?
O1 C19 C20 C21 49.7(3) . . . . ?
C5 C19 C20 C21 -131.2(2) . . . . ?
C25 C20 C21 C22 -1.5(4) . . . . ?
C19 C20 C21 C22 -179.8(2) . . . . ?
C20 C21 C22 C23 1.2(5) . . . . ?
C21 C22 C23 C24 0.3(5) . . . . ?
C22 C23 C24 C25 -1.3(5) . . . . ?
C21 C20 C25 C24 0.4(4) . . . . ?
C19 C20 C25 C24 178.7(2) . . . . ?
C23 C24 C25 C20 1.0(4) . . . . ?

_refine_diff_density_max         0.802
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.068




_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_NTT028F1
_database_code_depnum_ccdc_archive 'CCDC 2163447'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
;
'5-benzoyl-2-phenyl-4-(4-(trifluoromethyl)phenyl)thiophene-3-carbonitrile'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H14 F3 N O S'
_chemical_formula_sum            'C25 H14 F3 N O S'
_chemical_formula_weight         433.43

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'
F F 0.0171 0.0103 '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                   7.92109(18)
_cell_length_b                   9.58269(19)
_cell_length_c                   14.7540(3)
_cell_angle_alpha                99.4485(17)
_cell_angle_beta                 102.5251(19)
_cell_angle_gamma                100.8471(18)
_cell_volume                     1048.89(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    15437
_cell_measurement_theta_min      2.7240
_cell_measurement_theta_max      29.4090

_exptl_crystal_description       tab
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.145
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0592
0 0 -1 0.0854
-5 -2 4 0.1807
2 1 -5 0.0754
5 2 -5 0.0920
2 -5 -1 0.1047
-2 5 2 0.0439
-1 -5 4 0.1395
-3 1 5 0.1322
4 0 5 0.0806
2 -5 5 0.0618
1 4 -5 0.0797
5 -4 -5 0.0891
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_min  0.420
_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 (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            27479
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.373
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4598
_reflns_number_gt                4140
_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 1.171.41.108a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.108a (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)+(0.0712P)²+0.3277P] 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         4598
_refine_ls_number_parameters     317
_refine_ls_number_restraints     177
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1323
_refine_ls_wR_factor_gt          0.1284
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.243
_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
O1 O 0.89319(18) 0.63910(14) 0.50883(9) 0.0582(3) Uani 1 1 d . . . . .
N1 N 0.3224(3) 0.2184(2) 0.71498(12) 0.0755(6) Uani 1 1 d . . . . .
S1 S 0.65070(5) 0.35348(4) 0.47177(3) 0.04260(14) Uani 1 1 d . . . . .
C2 C 0.50105(18) 0.24834(15) 0.51551(10) 0.0359(3) Uani 1 1 d . . . . .
C3 C 0.52364(19) 0.30682(16) 0.61088(10) 0.0368(3) Uani 1 1 d . . . . .
C4 C 0.66753(19) 0.43261(15) 0.64937(10) 0.0363(3) Uani 1 1 d . . . . .
C5 C 0.74898(19) 0.46937(16) 0.58044(11) 0.0382(3) Uani 1 1 d . . . . .
C6 C 0.37649(19) 0.11784(15) 0.45126(10) 0.0370(3) Uani 1 1 d . . . . .
C7 C 0.3894(2) 0.07806(18) 0.35817(12) 0.0458(4) Uani 1 1 d . . . . .
H7 H 0.479614 0.131982 0.338348 0.055 Uiso 1 1 calc R U . . .
C8 C 0.2703(3) -0.04012(19) 0.29475(12) 0.0545(4) Uani 1 1 d . . . . .
H8 H 0.279397 -0.063350 0.232538 0.065 Uiso 1 1 calc R U . . .
C9 C 0.1382(2) -0.12361(18) 0.32347(13) 0.0524(4) Uani 1 1 d . . . . .
H9 H 0.056355 -0.201547 0.280445 0.063 Uiso 1 1 calc R U . . .
C10 C 0.1286(2) -0.09067(18) 0.41620(13) 0.0511(4) Uani 1 1 d . . . . .
H10 H 0.043184 -0.149359 0.436562 0.061 Uiso 1 1 calc R U . . .
C11 C 0.2455(2) 0.02955(18) 0.47979(12) 0.0461(4) Uani 1 1 d . . . . .
H11 H 0.236211 0.051395 0.542050 0.055 Uiso 1 1 calc R U . . .
C12 C 0.4104(2) 0.25543(19) 0.66775(11) 0.0476(4) Uani 1 1 d . . . . .
C13 C 0.7127(2) 0.51461(16) 0.74916(11) 0.0393(3) Uani 1 1 d . . . . .
C18 C 0.7313(3) 0.44374(19) 0.82430(12) 0.0535(4) Uani 1 1 d . . . . .
H18 H 0.714069 0.343043 0.812166 0.064 Uiso 1 1 calc R U . . .
C14 C 0.7384(2) 0.66475(18) 0.76882(12) 0.0475(4) Uani 1 1 d . . . . .
H14 H 0.724154 0.713444 0.719100 0.057 Uiso 1 1 calc R U . . .
C17 C 0.7753(3) 0.5216(2) 0.91697(14) 0.0686(6) Uani 1 1 d . . . . .
H17 H 0.786323 0.473397 0.966993 0.082 Uiso 1 1 calc R U . . .
C15 C 0.7848(3) 0.7426(2) 0.86153(14) 0.0615(5) Uani 1 1 d . . . . .
H15 H 0.803979 0.843466 0.874091 0.074 Uiso 1 1 calc R U . . .
C16 C 0.8028(4) 0.6711(2) 0.93509(15) 0.0740(6) Uani 1 1 d D U . . .
C20 C 0.8955(2) 0.59262(16) 0.58126(11) 0.0417(3) Uani 1 1 d . . . . .
C21 C 1.0423(2) 0.65420(17) 0.66846(12) 0.0438(3) Uani 1 1 d . . . . .
C22 C 1.1095(3) 0.80483(19) 0.69344(14) 0.0558(4) Uani 1 1 d . . . . .
H22 H 1.062951 0.864051 0.655508 0.067 Uiso 1 1 calc R U . . .
C23 C 1.2447(3) 0.8651(3) 0.77432(17) 0.0741(6) Uani 1 1 d . . . . .
H23 H 1.286209 0.965607 0.792672 0.089 Uiso 1 1 calc R U . . .
C24 C 1.3182(3) 0.7774(3) 0.82778(19) 0.0863(8) Uani 1 1 d . . . . .
H24 H 1.409963 0.818809 0.882237 0.104 Uiso 1 1 calc R U . . .
C26 C 1.1173(2) 0.5662(2) 0.72273(15) 0.0573(4) Uani 1 1 d . . . . .
H26 H 1.073528 0.465912 0.706072 0.069 Uiso 1 1 calc R U . . .
C25 C 1.2576(3) 0.6277(3) 0.80181(18) 0.0800(7) Uani 1 1 d . . . . .
H25 H 1.311121 0.568809 0.837419 0.096 Uiso 1 1 calc R U . . .
C19 C 0.8740(9) 0.7594(8) 1.0352(4) 0.1081(9) Uani 0.594(4) 1 d D U P A 1
F1 F 0.8304(8) 0.6787(6) 1.0973(3) 0.1417(14) Uani 0.594(4) 1 d D U P A 1
F2 F 0.7914(8) 0.8693(5) 1.0453(3) 0.1453(14) Uani 0.594(4) 1 d D U P A 1
F3 F 1.0453(6) 0.8107(5) 1.0623(2) 0.1422(12) Uani 0.594(4) 1 d D U P A 1
C19B C 0.8213(12) 0.7495(10) 1.0338(6) 0.1039(10) Uani 0.406(4) 1 d D U P A 2
F1B F 0.6772(8) 0.7587(8) 1.0593(3) 0.1406(15) Uani 0.406(4) 1 d D U P A 2
F2B F 0.9205(11) 0.8886(6) 1.0523(4) 0.1409(17) Uani 0.406(4) 1 d D U P A 2
F3B F 0.9221(10) 0.6942(9) 1.0995(5) 0.1385(17) Uani 0.406(4) 1 d D 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
O1 C20 1.2213(19) . ?
N1 C12 1.138(2) . ?
S1 C2 1.7124(14) . ?
S1 C5 1.7200(15) . ?
C2 C3 1.386(2) . ?
C2 C6 1.475(2) . ?
C3 C12 1.431(2) . ?
C3 C4 1.433(2) . ?
C4 C5 1.375(2) . ?
C4 C13 1.483(2) . ?
C5 C20 1.489(2) . ?
C6 C7 1.395(2) . ?
C6 C11 1.395(2) . ?
C7 C8 1.384(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.379(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.375(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.390(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C13 C14 1.387(2) . ?
C13 C18 1.388(2) . ?
C18 C17 1.381(3) . ?
C18 H18 0.9300 . ?
C14 C15 1.381(3) . ?
C14 H14 0.9300 . ?
C17 C16 1.380(3) . ?
C17 H17 0.9300 . ?
C15 C16 1.371(3) . ?
C15 H15 0.9300 . ?
C16 C19B 1.488(9) . ?
C16 C19 1.505(6) . ?
C20 C21 1.483(2) . ?
C21 C26 1.381(2) . ?
C21 C22 1.398(2) . ?
C22 C23 1.375(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.368(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.384(4) . ?
C24 H24 0.9300 . ?
C26 C25 1.382(3) . ?
C26 H26 0.9300 . ?
C25 H25 0.9300 . ?
C19 F3 1.301(7) . ?
C19 F2 1.345(8) . ?
C19 F1 1.352(8) . ?
C19B F1B 1.290(9) . ?
C19B F3B 1.360(10) . ?
C19B F2B 1.365(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C5 93.13(7) . . ?
C3 C2 C6 131.36(13) . . ?
C3 C2 S1 109.71(11) . . ?
C6 C2 S1 118.92(11) . . ?
C2 C3 C12 124.86(14) . . ?
C2 C3 C4 114.31(13) . . ?
C12 C3 C4 120.74(14) . . ?
C5 C4 C3 110.84(13) . . ?
C5 C4 C13 125.70(13) . . ?
C3 C4 C13 123.37(13) . . ?
C4 C5 C20 132.50(14) . . ?
C4 C5 S1 111.93(11) . . ?
C20 C5 S1 115.45(11) . . ?
C7 C6 C11 117.63(14) . . ?
C7 C6 C2 119.62(14) . . ?
C11 C6 C2 122.74(14) . . ?
C8 C7 C6 121.23(16) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C9 C8 C7 120.25(16) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 119.46(16) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 120.57(16) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C6 120.73(16) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
N1 C12 C3 177.9(2) . . ?
C14 C13 C18 118.81(15) . . ?
C14 C13 C4 120.09(14) . . ?
C18 C13 C4 121.10(14) . . ?
C17 C18 C13 120.51(17) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C15 C14 C13 120.61(16) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C17 C18 119.79(18) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C16 C15 C14 119.94(18) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.33(18) . . ?
C15 C16 C19B 120.5(4) . . ?
C17 C16 C19B 118.3(4) . . ?
C15 C16 C19 118.7(3) . . ?
C17 C16 C19 120.6(3) . . ?
O1 C20 C21 121.45(14) . . ?
O1 C20 C5 118.72(15) . . ?
C21 C20 C5 119.82(13) . . ?
C26 C21 C22 119.85(17) . . ?
C26 C21 C20 121.64(15) . . ?
C22 C21 C20 118.46(16) . . ?
C23 C22 C21 119.8(2) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C24 C23 C22 120.0(2) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.8(2) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C21 C26 C25 119.81(19) . . ?
C21 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C26 C25 C24 119.7(2) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
F3 C19 F2 109.6(6) . . ?
F3 C19 F1 107.0(6) . . ?
F2 C19 F1 105.2(6) . . ?
F3 C19 C16 115.6(5) . . ?
F2 C19 C16 108.7(5) . . ?
F1 C19 C16 110.1(5) . . ?
F1B C19B F3B 107.5(8) . . ?
F1B C19B F2B 106.0(8) . . ?
F3B C19B F2B 100.5(7) . . ?
F1B C19B C16 117.5(7) . . ?
F3B C19B C16 112.0(7) . . ?
F2B C19B C16 111.9(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 S1 C2 C3 2.53(11) . . . . ?
C5 S1 C2 C6 -177.18(12) . . . . ?
C6 C2 C3 C12 -6.7(3) . . . . ?
S1 C2 C3 C12 173.60(13) . . . . ?
C6 C2 C3 C4 176.84(14) . . . . ?
S1 C2 C3 C4 -2.82(16) . . . . ?
C2 C3 C4 C5 1.63(19) . . . . ?
C12 C3 C4 C5 -174.96(14) . . . . ?
C2 C3 C4 C13 178.44(13) . . . . ?
C12 C3 C4 C13 1.9(2) . . . . ?
C3 C4 C5 C20 176.23(15) . . . . ?
C13 C4 C5 C20 -0.5(3) . . . . ?
C3 C4 C5 S1 0.35(16) . . . . ?
C13 C4 C5 S1 -176.38(12) . . . . ?
C2 S1 C5 C4 -1.67(12) . . . . ?
C2 S1 C5 C20 -178.31(12) . . . . ?
C3 C2 C6 C7 -176.03(15) . . . . ?
S1 C2 C6 C7 3.60(19) . . . . ?
C3 C2 C6 C11 3.1(2) . . . . ?
S1 C2 C6 C11 -177.23(12) . . . . ?
C11 C6 C7 C8 3.5(2) . . . . ?
C2 C6 C7 C8 -177.32(15) . . . . ?
C6 C7 C8 C9 -1.6(3) . . . . ?
C7 C8 C9 C10 -1.6(3) . . . . ?
C8 C9 C10 C11 2.9(3) . . . . ?
C9 C10 C11 C6 -1.0(3) . . . . ?
C7 C6 C11 C10 -2.2(2) . . . . ?
C2 C6 C11 C10 178.65(15) . . . . ?
C5 C4 C13 C14 45.4(2) . . . . ?
C3 C4 C13 C14 -130.92(16) . . . . ?
C5 C4 C13 C18 -134.09(18) . . . . ?
C3 C4 C13 C18 49.6(2) . . . . ?
C14 C13 C18 C17 -0.2(3) . . . . ?
C4 C13 C18 C17 179.29(18) . . . . ?
C18 C13 C14 C15 1.2(3) . . . . ?
C4 C13 C14 C15 -178.35(16) . . . . ?
C13 C18 C17 C16 -0.7(4) . . . . ?
C13 C14 C15 C16 -1.2(3) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C14 C15 C16 C19B -169.2(5) . . . . ?
C14 C15 C16 C19 173.0(4) . . . . ?
C18 C17 C16 C15 0.7(4) . . . . ?
C18 C17 C16 C19B 170.4(5) . . . . ?
C18 C17 C16 C19 -171.9(4) . . . . ?
C4 C5 C20 O1 -147.43(17) . . . . ?
S1 C5 C20 O1 28.34(19) . . . . ?
C4 C5 C20 C21 33.8(2) . . . . ?
S1 C5 C20 C21 -150.40(12) . . . . ?
O1 C20 C21 C26 -137.17(18) . . . . ?
C5 C20 C21 C26 41.5(2) . . . . ?
O1 C20 C21 C22 40.4(2) . . . . ?
C5 C20 C21 C22 -140.91(15) . . . . ?
C26 C21 C22 C23 -2.9(3) . . . . ?
C20 C21 C22 C23 179.50(17) . . . . ?
C21 C22 C23 C24 2.8(3) . . . . ?
C22 C23 C24 C25 -0.3(4) . . . . ?
C22 C21 C26 C25 0.4(3) . . . . ?
C20 C21 C26 C25 177.96(19) . . . . ?
C21 C26 C25 C24 2.1(4) . . . . ?
C23 C24 C25 C26 -2.2(4) . . . . ?
C15 C16 C19 F3 -78.1(7) . . . . ?
C17 C16 C19 F3 94.6(6) . . . . ?
C15 C16 C19 F2 45.7(7) . . . . ?
C17 C16 C19 F2 -141.6(5) . . . . ?
C15 C16 C19 F1 160.5(5) . . . . ?
C17 C16 C19 F1 -26.8(7) . . . . ?
C15 C16 C19B F1B 86.0(9) . . . . ?
C17 C16 C19B F1B -83.8(9) . . . . ?
C15 C16 C19B F3B -149.0(6) . . . . ?
C17 C16 C19B F3B 41.3(9) . . . . ?
C15 C16 C19B F2B -37.0(9) . . . . ?
C17 C16 C19B F2B 153.3(6) . . . . ?

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.044



_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_tp304ef1_0m
_database_code_depnum_ccdc_archive 'CCDC 2163446'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2022-04-12 deposited with the CCDC.	2022-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
;
'5-benzoyl-2-(4-chlorophenyl)-4-phenylthiophene-3-carbonitrile'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H14 Cl N O S'
_chemical_formula_sum            'C24 H14 Cl N O S'
_chemical_formula_weight         399.87

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'
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'
N N 0.0061 0.0033 '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                   9.6404(5)
_cell_length_b                   9.9855(6)
_cell_length_c                   11.0770(7)
_cell_angle_alpha                70.189(2)
_cell_angle_beta                 88.960(2)
_cell_angle_gamma                74.740(2)
_cell_volume                     964.87(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7035
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.68


_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.394
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.067
_exptl_absorpt_coefficient_mu    0.321
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.671
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0748 before and 0.0595 after correction.
The Ratio of minimum to maximum transmission is 0.9000.The λ/2 correction 
factor is Not present.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_reflns_number            16099
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.683
_diffrn_reflns_theta_max         26.726
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4079
_reflns_number_gt                2814
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0130P)²+0.8844P] 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         4079
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.48500(7) 0.29016(8) 0.58414(7) 0.0512(2) Uani 1 1 d . . . . .
N1 N 0.9497(2) 0.1613(3) 0.3749(2) 0.0546(6) Uani 1 1 d . . . . .
O1 O 0.4578(2) 0.4300(3) 0.7740(2) 0.0818(7) Uani 1 1 d . . . . .
Cl1 Cl 0.32013(10) 0.09567(11) 0.06819(9) 0.0839(3) Uani 1 1 d . . . . .
C4 C 0.7522(2) 0.2831(2) 0.6055(2) 0.0379(5) Uani 1 1 d . . . . .
C3 C 0.7335(2) 0.2346(3) 0.5006(2) 0.0382(5) Uani 1 1 d . . . . .
C2 C 0.5939(2) 0.2327(3) 0.4772(2) 0.0399(5) Uani 1 1 d . . . . .
C5 C 0.6251(2) 0.3142(3) 0.6624(2) 0.0431(6) Uani 1 1 d . . . . .
C11 C 0.5996(3) 0.1845(3) 0.2687(3) 0.0525(7) Uani 1 1 d . . . . .
H11 H 0.690569 0.200508 0.258573 0.063 Uiso 1 1 calc R U . . .
C7 C 0.3938(3) 0.1691(3) 0.3897(3) 0.0484(6) Uani 1 1 d . . . . .
H7 H 0.345464 0.173647 0.462253 0.058 Uiso 1 1 calc R U . . .
C6 C 0.5297(2) 0.1937(3) 0.3777(2) 0.0413(6) Uani 1 1 d . . . . .
C9 C 0.4017(3) 0.1296(3) 0.1893(3) 0.0495(6) Uani 1 1 d . . . . .
C10 C 0.5360(3) 0.1520(3) 0.1754(3) 0.0542(7) Uani 1 1 d . . . . .
H10 H 0.584288 0.145280 0.103265 0.065 Uiso 1 1 calc R U . . .
C8 C 0.3290(3) 0.1381(3) 0.2956(3) 0.0540(7) Uani 1 1 d . . . . .
H8 H 0.237571 0.123168 0.304139 0.065 Uiso 1 1 calc R U . . .
C19 C 0.5842(3) 0.3682(3) 0.7705(3) 0.0498(6) Uani 1 1 d . . . . .
C12 C 0.8522(3) 0.1935(3) 0.4291(2) 0.0397(5) Uani 1 1 d . . . . .
C20 C 0.6941(3) 0.3484(3) 0.8722(2) 0.0434(6) Uani 1 1 d . . . . .
C13 C 0.8893(2) 0.3065(3) 0.6411(2) 0.0383(5) Uani 1 1 d . . . . .
C21 C 0.6785(3) 0.4598(3) 0.9228(3) 0.0574(7) Uani 1 1 d . . . . .
H21 H 0.598858 0.542157 0.895644 0.069 Uiso 1 1 calc R U . . .
C14 C 0.8898(3) 0.4433(3) 0.6461(2) 0.0482(6) Uani 1 1 d . . . . .
H14 H 0.805898 0.521016 0.622398 0.058 Uiso 1 1 calc R U . . .
C22 C 0.7809(4) 0.4493(4) 1.0136(3) 0.0737(9) Uani 1 1 d . . . . .
H22 H 0.771340 0.525574 1.046003 0.088 Uiso 1 1 calc R U . . .
C15 C 1.0145(3) 0.4644(4) 0.6863(3) 0.0628(8) Uani 1 1 d . . . . .
H15 H 1.013902 0.555885 0.690818 0.075 Uiso 1 1 calc R U . . .
C23 C 0.8966(4) 0.3262(4) 1.0561(3) 0.0741(9) Uani 1 1 d . . . . .
H23 H 0.966542 0.320116 1.115929 0.089 Uiso 1 1 calc R U . . .
C16 C 1.1384(3) 0.3518(4) 0.7194(3) 0.0726(10) Uani 1 1 d . . . . .
H16 H 1.221891 0.366271 0.747266 0.087 Uiso 1 1 calc R U . . .
C24 C 0.9092(3) 0.2121(4) 1.0105(3) 0.0645(8) Uani 1 1 d . . . . .
H24 H 0.985587 0.127073 1.042230 0.077 Uiso 1 1 calc R U . . .
C25 C 0.8093(3) 0.2230(3) 0.9179(2) 0.0494(6) Uani 1 1 d . . . . .
H25 H 0.819223 0.146191 0.886170 0.059 Uiso 1 1 calc R U . . .
C17 C 1.1404(3) 0.2171(4) 0.7116(3) 0.0691(9) Uani 1 1 d . . . . .
H17 H 1.225669 0.141038 0.733279 0.083 Uiso 1 1 calc R U . . .
C18 C 1.0160(3) 0.1935(3) 0.6716(3) 0.0513(7) Uani 1 1 d . . . . .
H18 H 1.017916 0.102422 0.665465 0.062 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 C2 1.712(2) . ?
S1 C5 1.729(2) . ?
N1 C12 1.140(3) . ?
O1 C19 1.219(3) . ?
Cl1 C9 1.738(3) . ?
C4 C5 1.378(3) . ?
C4 C3 1.433(3) . ?
C4 C13 1.483(3) . ?
C3 C2 1.382(3) . ?
C3 C12 1.430(3) . ?
C2 C6 1.480(3) . ?
C5 C19 1.479(3) . ?
C11 C10 1.381(3) . ?
C11 C6 1.391(4) . ?
C11 H11 0.9300 . ?
C7 C8 1.385(4) . ?
C7 C6 1.392(3) . ?
C7 H7 0.9300 . ?
C9 C10 1.369(4) . ?
C9 C8 1.374(4) . ?
C10 H10 0.9300 . ?
C8 H8 0.9300 . ?
C19 C20 1.487(3) . ?
C20 C21 1.381(3) . ?
C20 C25 1.384(3) . ?
C13 C18 1.382(3) . ?
C13 C14 1.388(3) . ?
C21 C22 1.381(4) . ?
C21 H21 0.9300 . ?
C14 C15 1.379(4) . ?
C14 H14 0.9300 . ?
C22 C23 1.371(5) . ?
C22 H22 0.9300 . ?
C15 C16 1.362(4) . ?
C15 H15 0.9300 . ?
C23 C24 1.372(4) . ?
C23 H23 0.9300 . ?
C16 C17 1.372(4) . ?
C16 H16 0.9300 . ?
C24 C25 1.377(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C17 C18 1.389(4) . ?
C17 H17 0.9300 . ?
C18 H18 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
C2 S1 C5 93.14(12) . . ?
C5 C4 C3 111.5(2) . . ?
C5 C4 C13 124.9(2) . . ?
C3 C4 C13 123.5(2) . . ?
C2 C3 C12 125.0(2) . . ?
C2 C3 C4 114.0(2) . . ?
C12 C3 C4 121.1(2) . . ?
C3 C2 C6 130.8(2) . . ?
C3 C2 S1 110.17(18) . . ?
C6 C2 S1 118.98(17) . . ?
C4 C5 C19 133.7(2) . . ?
C4 C5 S1 111.22(18) . . ?
C19 C5 S1 114.99(17) . . ?
C10 C11 C6 121.0(2) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C8 C7 C6 121.3(3) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C11 C6 C7 117.9(2) . . ?
C11 C6 C2 122.0(2) . . ?
C7 C6 C2 120.1(2) . . ?
C10 C9 C8 121.0(2) . . ?
C10 C9 Cl1 119.2(2) . . ?
C8 C9 Cl1 119.8(2) . . ?
C9 C10 C11 119.7(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C9 C8 C7 119.1(2) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
O1 C19 C5 118.3(2) . . ?
O1 C19 C20 120.7(2) . . ?
C5 C19 C20 121.1(2) . . ?
N1 C12 C3 177.7(3) . . ?
C21 C20 C25 119.3(2) . . ?
C21 C20 C19 118.0(2) . . ?
C25 C20 C19 122.6(2) . . ?
C18 C13 C14 119.4(2) . . ?
C18 C13 C4 121.1(2) . . ?
C14 C13 C4 119.4(2) . . ?
C22 C21 C20 120.2(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C23 C22 C21 120.0(3) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C22 C23 C24 120.1(3) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C15 C16 C17 120.2(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C23 C24 C25 120.3(3) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C20 120.0(3) . . ?
C24 C25 H25 120.0 . . ?
C20 C25 H25 120.0 . . ?
C16 C17 C18 120.5(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 119.4(3) . . ?
C13 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?

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
C5 C4 C3 C2 1.4(3) . . . . ?
C13 C4 C3 C2 -174.5(2) . . . . ?
C5 C4 C3 C12 -178.8(2) . . . . ?
C13 C4 C3 C12 5.2(3) . . . . ?
C12 C3 C2 C6 -1.3(4) . . . . ?
C4 C3 C2 C6 178.4(2) . . . . ?
C12 C3 C2 S1 -179.88(19) . . . . ?
C4 C3 C2 S1 -0.1(3) . . . . ?
C5 S1 C2 C3 -0.92(19) . . . . ?
C5 S1 C2 C6 -179.67(19) . . . . ?
C3 C4 C5 C19 -179.2(3) . . . . ?
C13 C4 C5 C19 -3.3(4) . . . . ?
C3 C4 C5 S1 -2.1(3) . . . . ?
C13 C4 C5 S1 173.82(19) . . . . ?
C2 S1 C5 C4 1.8(2) . . . . ?
C2 S1 C5 C19 179.5(2) . . . . ?
C10 C11 C6 C7 0.0(4) . . . . ?
C10 C11 C6 C2 -178.2(2) . . . . ?
C8 C7 C6 C11 -0.7(4) . . . . ?
C8 C7 C6 C2 177.5(2) . . . . ?
C3 C2 C6 C11 -15.8(4) . . . . ?
S1 C2 C6 C11 162.6(2) . . . . ?
C3 C2 C6 C7 166.0(2) . . . . ?
S1 C2 C6 C7 -15.5(3) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
Cl1 C9 C10 C11 177.6(2) . . . . ?
C6 C11 C10 C9 0.5(4) . . . . ?
C10 C9 C8 C7 -0.3(4) . . . . ?
Cl1 C9 C8 C7 -178.3(2) . . . . ?
C6 C7 C8 C9 0.9(4) . . . . ?
C4 C5 C19 O1 156.7(3) . . . . ?
S1 C5 C19 O1 -20.4(3) . . . . ?
C4 C5 C19 C20 -23.1(4) . . . . ?
S1 C5 C19 C20 159.8(2) . . . . ?
O1 C19 C20 C21 -36.0(4) . . . . ?
C5 C19 C20 C21 143.7(3) . . . . ?
O1 C19 C20 C25 143.4(3) . . . . ?
C5 C19 C20 C25 -36.8(4) . . . . ?
C5 C4 C13 C18 127.0(3) . . . . ?
C3 C4 C13 C18 -57.5(3) . . . . ?
C5 C4 C13 C14 -51.7(3) . . . . ?
C3 C4 C13 C14 123.7(3) . . . . ?
C25 C20 C21 C22 3.2(4) . . . . ?
C19 C20 C21 C22 -177.4(3) . . . . ?
C18 C13 C14 C15 -2.6(4) . . . . ?
C4 C13 C14 C15 176.2(2) . . . . ?
C20 C21 C22 C23 -1.6(5) . . . . ?
C13 C14 C15 C16 1.0(4) . . . . ?
C21 C22 C23 C24 -1.4(5) . . . . ?
C14 C15 C16 C17 0.7(5) . . . . ?
C22 C23 C24 C25 2.7(5) . . . . ?
C23 C24 C25 C20 -1.1(4) . . . . ?
C21 C20 C25 C24 -1.8(4) . . . . ?
C19 C20 C25 C24 178.8(3) . . . . ?
C15 C16 C17 C18 -0.8(5) . . . . ?
C14 C13 C18 C17 2.4(4) . . . . ?
C4 C13 C18 C17 -176.3(2) . . . . ?
C16 C17 C18 C13 -0.8(4) . . . . ?

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.047




_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_NTT028F2
_database_code_depnum_ccdc_archive 'CCDC 2163448'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
;
'(5-amino-3-(4-(trifluoromethyl)phenyl)thiophene-2,4-diyl)bis(phenylmethanone)'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H16 F3 N O2 S'
_chemical_formula_sum            'C25 H16 F3 N O2 S'
_chemical_formula_weight         451.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   26.6681(8)
_cell_length_b                   9.3197(2)
_cell_length_c                   18.2235(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.917(3)
_cell_angle_gamma                90
_cell_volume                     4376.6(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    21811
_cell_measurement_theta_min      2.6270
_cell_measurement_theta_max      28.8750

_exptl_crystal_description       tab
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_size_max          0.349
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.116
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_F_000             1856.000
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 2 0 0.0229
-5 -3 -4 0.0533
-4 -5 0 0.0899
4 0 5 0.2047
1 0 0 0.1090
3 0 -5 0.0717
-1 0 0 0.0497
-5 0 4 0.2357
1 -5 3 0.1419
-3 4 -5 0.0450
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_min  0.763
_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.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.593
_oxdiff_exptl_absorpt_empirical_full_max 1.280
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_detector                 'Dectris PILATUS3 R 200K-A area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'Hybrid Photon Counting area detector'

_diffrn_measurement_device       'kappa gonio four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'

_diffrn_radiation_collimation    
'Rigaku Integrated Confocal MaxFlux double bounce multi-layer mirror optics'
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          x-ray

_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku micromax 003'
_diffrn_reflns_number            55784
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.313
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8627
_reflns_number_gt                7402
_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)+(0.0586P)²+1.5104P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8624
_refine_ls_number_parameters     649
_refine_ls_number_restraints     327
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.1156
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.819
_refine_ls_shift/su_max          0.001
_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 0.25600(7) 0.08375(18) 0.51445(10) 0.0609(4) Uani 1 1 d D . . . .
H1N1_1 H 0.2506(9) 0.017(2) 0.5482(12) 0.091(8) Uiso 1 1 d D . . . .
H1N2_1 H 0.2817(7) 0.067(2) 0.4904(11) 0.071(6) Uiso 1 1 d D . . . .
O1_1 O 0.21712(7) 0.60106(18) 0.37543(9) 0.0829(5) Uani 1 1 d . . . . .
C26_1 C 0.09269(9) 0.6365(3) 0.38952(13) 0.0743(6) Uani 1 1 d . . . . .
H26_1 H 0.084236 0.541258 0.376844 0.089 Uiso 1 1 calc R U . . .
S1_1 S 0.24002(2) 0.32855(5) 0.43922(3) 0.05621(14) Uani 1 1 d . . . . .
O2_1 O 0.19730(7) 0.04221(15) 0.61067(9) 0.0805(5) Uani 1 1 d . . . . .
C2_1 C 0.23097(6) 0.20504(17) 0.50564(9) 0.0419(3) Uani 1 1 d . . . . .
C3_1 C 0.19542(6) 0.25873(18) 0.54643(9) 0.0454(4) Uani 1 1 d . . . . .
F1_1 F -0.0116(2) 0.7407(11) 0.5979(4) 0.143(3) Uani 0.473(7) 1 d D U P A 1
F2_1 F 0.0193(3) 0.6380(7) 0.7004(5) 0.145(2) Uani 0.473(7) 1 d D U P A 1
F3_1 F 0.0484(3) 0.8405(7) 0.6748(6) 0.124(2) Uani 0.473(7) 1 d D U P A 1
F1B_1 F -0.0061(2) 0.6552(6) 0.6481(6) 0.135(2) Uani 0.527(7) 1 d D U P A 1
F2B_1 F 0.0529(3) 0.7985(9) 0.6966(4) 0.138(3) Uani 0.527(7) 1 d D U P A 1
F3B_1 F 0.0077(3) 0.8235(8) 0.5828(4) 0.165(2) Uani 0.527(7) 1 d D U P A 1
C20_1 C 0.18694(8) 0.5764(2) 0.41487(10) 0.0571(4) Uani 1 1 d . . . . .
C5_1 C 0.19528(7) 0.44737(19) 0.46135(9) 0.0493(4) Uani 1 1 d . . . . .
C4_1 C 0.17543(6) 0.39708(17) 0.51952(9) 0.0440(3) Uani 1 1 d . . . . .
C21_1 C 0.14402(8) 0.6782(2) 0.41305(10) 0.0573(5) Uani 1 1 d . . . . .
C6_1 C 0.18498(7) 0.16995(19) 0.60684(10) 0.0514(4) Uani 1 1 d . . . . .
C22_1 C 0.15609(10) 0.8203(2) 0.43142(13) 0.0755(6) Uani 1 1 d . . . . .
H22_1 H 0.190627 0.849112 0.445498 0.091 Uiso 1 1 calc R U . . .
C7_1 C 0.15965(7) 0.22421(19) 0.66537(9) 0.0495(4) Uani 1 1 d . . . . .
C23_1 C 0.11790(14) 0.9181(3) 0.42907(17) 0.0975(8) Uani 1 1 d . . . . .
H23_1 H 0.126395 1.012702 0.443302 0.117 Uiso 1 1 calc R U . . .
C8_1 C 0.11924(8) 0.1432(2) 0.67903(12) 0.0660(5) Uani 1 1 d . . . . .
H8_1 H 0.108710 0.059703 0.651395 0.079 Uiso 1 1 calc R U . . .
C24_1 C 0.06679(14) 0.8773(4) 0.4057(2) 0.1105(11) Uani 1 1 d . . . . .
H24_1 H 0.040635 0.944251 0.403788 0.133 Uiso 1 1 calc R U . . .
C9_1 C 0.09473(10) 0.1858(3) 0.73322(15) 0.0824(7) Uani 1 1 d . . . . .
H9_1 H 0.066972 0.133069 0.741075 0.099 Uiso 1 1 calc R U . . .
C25_1 C 0.05425(10) 0.7365(4) 0.38496(18) 0.1022(10) Uani 1 1 d . . . . .
H25_1 H 0.019630 0.709409 0.367867 0.123 Uiso 1 1 calc R U . . .
C10_1 C 0.11135(11) 0.3061(3) 0.77548(14) 0.0868(7) Uani 1 1 d . . . . .
H10_1 H 0.094826 0.334513 0.812230 0.104 Uiso 1 1 calc R U . . .
C11_1 C 0.15221(9) 0.3853(3) 0.76426(12) 0.0761(6) Uani 1 1 d . . . . .
H11_1 H 0.163572 0.465990 0.793923 0.091 Uiso 1 1 calc R U . . .
C12_1 C 0.17641(7) 0.3451(2) 0.70882(10) 0.0571(4) Uani 1 1 d . . . . .
H12_1 H 0.203846 0.399060 0.700789 0.068 Uiso 1 1 calc R U . . .
C13_1 C 0.13812(6) 0.48037(17) 0.55046(9) 0.0432(3) Uani 1 1 d . . . . .
C17_1 C 0.11787(7) 0.6919(2) 0.61273(11) 0.0581(4) Uani 1 1 d . . . . .
H17_1 H 0.127639 0.781001 0.634722 0.070 Uiso 1 1 calc R U . . .
C14_1 C 0.08886(7) 0.42699(19) 0.54736(10) 0.0496(4) Uani 1 1 d . . . . .
H14_1 H 0.078904 0.338085 0.525200 0.060 Uiso 1 1 calc R U . . .
C16_1 C 0.06929(7) 0.6375(2) 0.60964(11) 0.0583(4) Uani 1 1 d . . . . .
C15_1 C 0.05488(7) 0.5048(2) 0.57683(11) 0.0568(4) Uani 1 1 d . . . . .
H15_1 H 0.022091 0.468216 0.574743 0.068 Uiso 1 1 calc R U . . .
C19_1 C 0.03186(10) 0.7214(3) 0.64054(19) 0.0936(8) Uani 1 1 d . U . . .
C18_1 C 0.15185(7) 0.61381(19) 0.58317(10) 0.0506(4) Uani 1 1 d D . . . .
H18_1 H 0.184523 0.651072 0.585138 0.061 Uiso 1 1 calc R U . . .
N1_2 N 0.23643(6) -0.32278(17) 0.23091(9) 0.0537(4) Uani 1 1 d D . . . .
H1N1_2 H 0.2251(7) -0.359(2) 0.2695(9) 0.052(5) Uiso 1 1 d D . . . .
H1N2_2 H 0.2309(8) -0.366(2) 0.1866(10) 0.065(6) Uiso 1 1 d D . . . .
O1_2 O 0.32873(6) 0.10724(15) 0.42324(7) 0.0641(4) Uani 1 1 d . . . . .
C26_2 C 0.33030(8) 0.3361(2) 0.27257(12) 0.0624(5) Uani 1 1 d . . . . .
H26_2 H 0.299591 0.302300 0.240487 0.075 Uiso 1 1 calc R U . . .
S1_2 S 0.27502(2) -0.11697(5) 0.32914(2) 0.04956(12) Uani 1 1 d . . . . .
O2_2 O 0.26335(5) -0.29878(14) 0.09665(7) 0.0574(3) Uani 1 1 d . . . . .
C2_2 C 0.26732(6) -0.20939(17) 0.24481(9) 0.0424(3) Uani 1 1 d . . . . .
F1_2 F 0.4415(3) 0.4216(7) 0.0688(5) 0.127(2) Uani 0.461(5) 1 d D U P B 1
F2_2 F 0.48309(19) 0.2361(6) 0.0647(3) 0.1156(16) Uani 0.461(5) 1 d D U P B 1
F3_2 F 0.5023(3) 0.3562(9) 0.1630(3) 0.136(2) Uani 0.461(5) 1 d D U P B 1
F1B_2 F 0.4452(3) 0.3776(8) 0.0474(2) 0.126(2) Uani 0.539(5) 1 d D U P B 1
F2B_2 F 0.5092(2) 0.2718(5) 0.1205(5) 0.1405(19) Uani 0.539(5) 1 d D U P B 1
F3B_2 F 0.47517(19) 0.4483(4) 0.1569(2) 0.1043(14) Uani 0.539(5) 1 d D U P B 1
C3_2 C 0.29820(6) -0.14981(17) 0.19974(8) 0.0411(3) Uani 1 1 d . . . . .
C20_2 C 0.33272(6) 0.12311(19) 0.35768(9) 0.0479(4) Uani 1 1 d . . . . .
C5_2 C 0.31574(6) 0.00883(18) 0.30277(9) 0.0442(4) Uani 1 1 d . . . . .
C4_2 C 0.32530(6) -0.02434(17) 0.23388(8) 0.0395(3) Uani 1 1 d . . . . .
C21_2 C 0.35446(7) 0.26023(19) 0.33729(10) 0.0503(4) Uani 1 1 d . . . . .
C6_2 C 0.29989(6) -0.22194(17) 0.12896(9) 0.0439(4) Uani 1 1 d . . . . .
C22_2 C 0.39959(9) 0.3136(2) 0.38507(11) 0.0669(5) Uani 1 1 d . . . . .
H22_2 H 0.415261 0.264938 0.429626 0.080 Uiso 1 1 calc R U . . .
C7_2 C 0.34549(7) -0.21162(18) 0.09608(9) 0.0484(4) Uani 1 1 d . . . . .
C23_2 C 0.42143(11) 0.4382(3) 0.36714(15) 0.0851(7) Uani 1 1 d . . . . .
H23_2 H 0.452183 0.472328 0.398930 0.102 Uiso 1 1 calc R U . . .
C8_2 C 0.39587(7) -0.2138(2) 0.14020(11) 0.0573(4) Uani 1 1 d . . . . .
H8_2 H 0.402401 -0.217690 0.192806 0.069 Uiso 1 1 calc R U . . .
C24_2 C 0.39792(12) 0.5116(3) 0.30256(17) 0.0928(8) Uani 1 1 d . . . . .
H24_2 H 0.412943 0.595186 0.290132 0.111 Uiso 1 1 calc R U . . .
C9_2 C 0.43674(9) -0.2102(3) 0.10663(15) 0.0807(7) Uani 1 1 d . . . . .
H9_2 H 0.470736 -0.212077 0.136553 0.097 Uiso 1 1 calc R U . . .
C25_2 C 0.35223(11) 0.4626(2) 0.25602(15) 0.0828(7) Uani 1 1 d . . . . .
H25_2 H 0.335875 0.514778 0.213011 0.099 Uiso 1 1 calc R U . . .
C10_2 C 0.42714(11) -0.2040(4) 0.02959(17) 0.1056(10) Uani 1 1 d . . . . .
H10_2 H 0.454709 -0.200362 0.007094 0.127 Uiso 1 1 calc R U . . .
C11_2 C 0.37758(12) -0.2031(4) -0.01471(14) 0.1108(11) Uani 1 1 d . . . . .
H11_2 H 0.371481 -0.199131 -0.067268 0.133 Uiso 1 1 calc R U . . .
C12_2 C 0.33622(9) -0.2079(3) 0.01792(11) 0.0771(7) Uani 1 1 d . . . . .
H12_2 H 0.302370 -0.208701 -0.012524 0.093 Uiso 1 1 calc R U . . .
C13_2 C 0.36074(6) 0.06171(17) 0.20061(8) 0.0394(3) Uani 1 1 d . . . . .
C14_2 C 0.41181(6) 0.08293(19) 0.24190(9) 0.0470(4) Uani 1 1 d . . . . .
H14_2 H 0.423713 0.040793 0.289473 0.056 Uiso 1 1 calc R U . . .
C15_2 C 0.44476(7) 0.1655(2) 0.21300(10) 0.0542(4) Uani 1 1 d . . . . .
H15_2 H 0.478918 0.178868 0.240852 0.065 Uiso 1 1 calc R U . . .
C16_2 C 0.42723(7) 0.2289(2) 0.14260(10) 0.0520(4) Uani 1 1 d . . . . .
C17_2 C 0.37690(7) 0.20736(19) 0.10017(9) 0.0510(4) Uani 1 1 d . . . . .
H17_2 H 0.365241 0.249225 0.052485 0.061 Uiso 1 1 calc R U . . .
C19_2 C 0.46340(10) 0.3228(3) 0.11387(14) 0.0793(7) Uani 1 1 d . U . . .
C18_2 C 0.34401(6) 0.12283(18) 0.12933(9) 0.0452(4) Uani 1 1 d D . . . .
H18_2 H 0.310217 0.106883 0.100648 0.054 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
N1_1 C2_1 1.302(2) . ?
O1_1 C20_1 1.231(2) . ?
C26_1 C25_1 1.372(4) . ?
C26_1 C21_1 1.381(3) . ?
S1_1 C2_1 1.7317(16) . ?
S1_1 C5_1 1.7492(18) . ?
O2_1 C6_1 1.232(2) . ?
C2_1 C3_1 1.437(2) . ?
C3_1 C4_1 1.433(2) . ?
C3_1 C6_1 1.460(2) . ?
F1_1 F3B_1 1.004(8) . ?
F1_1 F1B_1 1.193(8) . ?
F1_1 C19_1 1.230(5) . ?
F2_1 F1B_1 1.029(7) . ?
F2_1 C19_1 1.448(6) . ?
F2_1 F2B_1 1.754(11) . ?
F3_1 F2B_1 0.549(15) . ?
F3_1 C19_1 1.294(7) . ?
F3_1 F3B_1 1.754(12) . ?
F1B_1 C19_1 1.223(5) . ?
F2B_1 C19_1 1.257(7) . ?
F3B_1 C19_1 1.442(6) . ?
C20_1 C5_1 1.455(2) . ?
C20_1 C21_1 1.480(3) . ?
C5_1 C4_1 1.383(2) . ?
C4_1 C13_1 1.483(2) . ?
C21_1 C22_1 1.383(3) . ?
C6_1 C7_1 1.490(2) . ?
C22_1 C23_1 1.359(4) . ?
C7_1 C12_1 1.383(3) . ?
C7_1 C8_1 1.390(3) . ?
C23_1 C24_1 1.373(4) . ?
C8_1 C9_1 1.376(3) . ?
C24_1 C25_1 1.383(5) . ?
C9_1 C10_1 1.367(4) . ?
C10_1 C11_1 1.375(3) . ?
C11_1 C12_1 1.383(3) . ?
C13_1 C18_1 1.387(2) . ?
C13_1 C14_1 1.392(2) . ?
C17_1 C18_1 1.375(3) . ?
C17_1 C16_1 1.379(3) . ?
C14_1 C15_1 1.373(3) . ?
C16_1 C15_1 1.385(3) . ?
C16_1 C19_1 1.488(3) . ?
N1_2 C2_2 1.324(2) . ?
O1_2 C20_2 1.235(2) . ?
C26_2 C21_2 1.384(3) . ?
C26_2 C25_2 1.384(3) . ?
S1_2 C2_2 1.7272(16) . ?
S1_2 C5_2 1.7474(16) . ?
O2_2 C6_2 1.230(2) . ?
C2_2 C3_2 1.417(2) . ?
F1_2 F1B_2 0.592(10) . ?
F1_2 C19_2 1.271(7) . ?
F1_2 F3B_2 1.644(9) . ?
F2_2 F2B_2 1.125(7) . ?
F2_2 C19_2 1.405(5) . ?
F2_2 F1B_2 1.641(9) . ?
F3_2 F3B_2 1.110(8) . ?
F3_2 F2B_2 1.151(7) . ?
F3_2 C19_2 1.224(5) . ?
F1B_2 C19_2 1.288(6) . ?
F2B_2 C19_2 1.288(5) . ?
F3B_2 C19_2 1.398(4) . ?
C3_2 C4_2 1.430(2) . ?
C3_2 C6_2 1.465(2) . ?
C20_2 C5_2 1.452(2) . ?
C20_2 C21_2 1.489(3) . ?
C5_2 C4_2 1.379(2) . ?
C4_2 C13_2 1.483(2) . ?
C21_2 C22_2 1.384(3) . ?
C6_2 C7_2 1.491(2) . ?
C22_2 C23_2 1.375(3) . ?
C7_2 C8_2 1.377(3) . ?
C7_2 C12_2 1.382(3) . ?
C23_2 C24_2 1.367(4) . ?
C8_2 C9_2 1.381(3) . ?
C24_2 C25_2 1.371(4) . ?
C9_2 C10_2 1.362(4) . ?
C10_2 C11_2 1.360(4) . ?
C11_2 C12_2 1.382(3) . ?
C13_2 C18_2 1.383(2) . ?
C13_2 C14_2 1.390(2) . ?
C14_2 C15_2 1.371(2) . ?
C15_2 C16_2 1.380(3) . ?
C16_2 C17_2 1.380(2) . ?
C16_2 C19_2 1.493(3) . ?
C17_2 C18_2 1.383(2) . ?

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
C25_1 C26_1 C21_1 119.6(2) . . ?
C2_1 S1_1 C5_1 91.93(8) . . ?
N1_1 C2_1 C3_1 128.64(15) . . ?
N1_1 C2_1 S1_1 120.28(12) . . ?
C3_1 C2_1 S1_1 111.06(12) . . ?
C4_1 C3_1 C2_1 111.92(14) . . ?
C4_1 C3_1 C6_1 129.92(15) . . ?
C2_1 C3_1 C6_1 118.16(15) . . ?
F3B_1 F1_1 F1B_1 138.9(7) . . ?
F3B_1 F1_1 C19_1 79.7(6) . . ?
F1B_1 F1_1 C19_1 60.6(4) . . ?
F1B_1 F2_1 C19_1 56.1(4) . . ?
F1B_1 F2_1 F2B_1 92.9(6) . . ?
C19_1 F2_1 F2B_1 45.0(3) . . ?
F2B_1 F3_1 C19_1 73.8(12) . . ?
F2B_1 F3_1 F3B_1 126.4(14) . . ?
C19_1 F3_1 F3B_1 53.9(4) . . ?
F2_1 F1B_1 F1_1 137.4(7) . . ?
F2_1 F1B_1 C19_1 79.5(5) . . ?
F1_1 F1B_1 C19_1 61.2(4) . . ?
F3_1 F2B_1 C19_1 81.4(14) . . ?
F3_1 F2B_1 F2_1 128.2(15) . . ?
C19_1 F2B_1 F2_1 54.5(4) . . ?
F1_1 F3B_1 C19_1 57.1(4) . . ?
F1_1 F3B_1 F3_1 92.4(6) . . ?
C19_1 F3B_1 F3_1 46.5(3) . . ?
O1_1 C20_1 C5_1 117.99(18) . . ?
O1_1 C20_1 C21_1 119.03(17) . . ?
C5_1 C20_1 C21_1 122.98(15) . . ?
C4_1 C5_1 C20_1 134.03(17) . . ?
C4_1 C5_1 S1_1 112.37(13) . . ?
C20_1 C5_1 S1_1 113.60(12) . . ?
C5_1 C4_1 C3_1 112.66(15) . . ?
C5_1 C4_1 C13_1 122.74(15) . . ?
C3_1 C4_1 C13_1 124.60(14) . . ?
C26_1 C21_1 C22_1 119.7(2) . . ?
C26_1 C21_1 C20_1 121.71(19) . . ?
C22_1 C21_1 C20_1 118.53(19) . . ?
O2_1 C6_1 C3_1 119.36(16) . . ?
O2_1 C6_1 C7_1 116.79(15) . . ?
C3_1 C6_1 C7_1 123.84(15) . . ?
C23_1 C22_1 C21_1 120.6(2) . . ?
C12_1 C7_1 C8_1 119.42(17) . . ?
C12_1 C7_1 C6_1 123.14(16) . . ?
C8_1 C7_1 C6_1 117.33(17) . . ?
C22_1 C23_1 C24_1 120.0(3) . . ?
C9_1 C8_1 C7_1 120.3(2) . . ?
C23_1 C24_1 C25_1 119.9(3) . . ?
C10_1 C9_1 C8_1 119.7(2) . . ?
C26_1 C25_1 C24_1 120.2(3) . . ?
C9_1 C10_1 C11_1 120.7(2) . . ?
C10_1 C11_1 C12_1 120.0(2) . . ?
C7_1 C12_1 C11_1 119.73(19) . . ?
C18_1 C13_1 C14_1 118.68(16) . . ?
C18_1 C13_1 C4_1 120.26(14) . . ?
C14_1 C13_1 C4_1 121.06(15) . . ?
C18_1 C17_1 C16_1 119.78(17) . . ?
C15_1 C14_1 C13_1 120.42(16) . . ?
C17_1 C16_1 C15_1 119.95(17) . . ?
C17_1 C16_1 C19_1 120.43(19) . . ?
C15_1 C16_1 C19_1 119.62(19) . . ?
C14_1 C15_1 C16_1 120.18(17) . . ?
F1B_1 C19_1 F1_1 58.2(4) . . ?
F1B_1 C19_1 F2B_1 113.9(5) . . ?
F1_1 C19_1 F2B_1 125.5(5) . . ?
F1B_1 C19_1 F3_1 124.5(5) . . ?
F1_1 C19_1 F3_1 109.1(5) . . ?
F2B_1 C19_1 F3_1 24.8(7) . . ?
F1B_1 C19_1 F3B_1 100.8(4) . . ?
F1_1 C19_1 F3B_1 43.2(4) . . ?
F2B_1 C19_1 F3B_1 103.8(5) . . ?
F3_1 C19_1 F3B_1 79.5(5) . . ?
F1B_1 C19_1 F2_1 44.3(4) . . ?
F1_1 C19_1 F2_1 101.0(5) . . ?
F2B_1 C19_1 F2_1 80.5(5) . . ?
F3_1 C19_1 F2_1 102.3(5) . . ?
F3B_1 C19_1 F2_1 139.2(4) . . ?
F1B_1 C19_1 C16_1 115.6(3) . . ?
F1_1 C19_1 C16_1 116.8(4) . . ?
F2B_1 C19_1 C16_1 114.0(4) . . ?
F3_1 C19_1 C16_1 117.1(4) . . ?
F3B_1 C19_1 C16_1 106.7(3) . . ?
F2_1 C19_1 C16_1 108.2(3) . . ?
C17_1 C18_1 C13_1 120.99(16) . . ?
C21_2 C26_2 C25_2 119.4(2) . . ?
C2_2 S1_2 C5_2 91.71(7) . . ?
N1_2 C2_2 C3_2 128.87(15) . . ?
N1_2 C2_2 S1_2 119.60(12) . . ?
C3_2 C2_2 S1_2 111.51(12) . . ?
F1B_2 F1_2 C19_2 78.3(11) . . ?
F1B_2 F1_2 F3B_2 127.3(14) . . ?
C19_2 F1_2 F3B_2 55.5(3) . . ?
F2B_2 F2_2 C19_2 60.0(3) . . ?
F2B_2 F2_2 F1B_2 98.2(4) . . ?
C19_2 F2_2 F1B_2 49.3(3) . . ?
F3B_2 F3_2 F2B_2 132.4(7) . . ?
F3B_2 F3_2 C19_2 73.4(5) . . ?
F2B_2 F3_2 C19_2 65.6(3) . . ?
F1_2 F1B_2 C19_2 75.0(10) . . ?
F1_2 F1B_2 F2_2 129.0(13) . . ?
C19_2 F1B_2 F2_2 55.8(3) . . ?
F2_2 F2B_2 F3_2 129.9(7) . . ?
F2_2 F2B_2 C19_2 70.9(4) . . ?
F3_2 F2B_2 C19_2 59.9(3) . . ?
F3_2 F3B_2 C19_2 57.1(3) . . ?
F3_2 F3B_2 F1_2 99.1(4) . . ?
C19_2 F3B_2 F1_2 48.6(3) . . ?
C2_2 C3_2 C4_2 111.84(14) . . ?
C2_2 C3_2 C6_2 118.98(14) . . ?
C4_2 C3_2 C6_2 129.15(13) . . ?
O1_2 C20_2 C5_2 119.31(16) . . ?
O1_2 C20_2 C21_2 118.69(16) . . ?
C5_2 C20_2 C21_2 121.99(14) . . ?
C4_2 C5_2 C20_2 133.95(15) . . ?
C4_2 C5_2 S1_2 111.94(12) . . ?
C20_2 C5_2 S1_2 114.10(11) . . ?
C5_2 C4_2 C3_2 112.84(14) . . ?
C5_2 C4_2 C13_2 122.53(14) . . ?
C3_2 C4_2 C13_2 124.62(13) . . ?
C26_2 C21_2 C22_2 119.44(19) . . ?
C26_2 C21_2 C20_2 121.69(17) . . ?
C22_2 C21_2 C20_2 118.87(17) . . ?
O2_2 C6_2 C3_2 119.22(14) . . ?
O2_2 C6_2 C7_2 118.21(15) . . ?
C3_2 C6_2 C7_2 122.50(14) . . ?
C23_2 C22_2 C21_2 120.5(2) . . ?
C8_2 C7_2 C12_2 119.40(17) . . ?
C8_2 C7_2 C6_2 122.60(15) . . ?
C12_2 C7_2 C6_2 117.89(17) . . ?
C24_2 C23_2 C22_2 119.9(2) . . ?
C7_2 C8_2 C9_2 120.26(19) . . ?
C23_2 C24_2 C25_2 120.2(2) . . ?
C10_2 C9_2 C8_2 119.8(2) . . ?
C24_2 C25_2 C26_2 120.5(2) . . ?
C11_2 C10_2 C9_2 120.6(2) . . ?
C10_2 C11_2 C12_2 120.4(2) . . ?
C11_2 C12_2 C7_2 119.6(2) . . ?
C18_2 C13_2 C14_2 118.95(14) . . ?
C18_2 C13_2 C4_2 121.42(13) . . ?
C14_2 C13_2 C4_2 119.62(13) . . ?
C15_2 C14_2 C13_2 120.48(15) . . ?
C14_2 C15_2 C16_2 120.01(16) . . ?
C15_2 C16_2 C17_2 120.41(15) . . ?
C15_2 C16_2 C19_2 118.81(18) . . ?
C17_2 C16_2 C19_2 120.77(18) . . ?
C16_2 C17_2 C18_2 119.29(15) . . ?
F3_2 C19_2 F1_2 116.8(5) . . ?
F3_2 C19_2 F2B_2 54.5(4) . . ?
F1_2 C19_2 F2B_2 126.5(5) . . ?
F3_2 C19_2 F1B_2 129.0(4) . . ?
F1_2 C19_2 F1B_2 26.7(5) . . ?
F2B_2 C19_2 F1B_2 110.7(4) . . ?
F3_2 C19_2 F3B_2 49.6(4) . . ?
F1_2 C19_2 F3B_2 75.9(4) . . ?
F2B_2 C19_2 F3B_2 100.7(4) . . ?
F1B_2 C19_2 F3B_2 99.9(4) . . ?
F3_2 C19_2 F2_2 103.1(4) . . ?
F1_2 C19_2 F2_2 100.9(4) . . ?
F2B_2 C19_2 F2_2 49.1(3) . . ?
F1B_2 C19_2 F2_2 74.9(4) . . ?
F3B_2 C19_2 F2_2 140.5(3) . . ?
F3_2 C19_2 C16_2 113.3(3) . . ?
F1_2 C19_2 C16_2 114.8(4) . . ?
F2B_2 C19_2 C16_2 115.7(3) . . ?
F1B_2 C19_2 C16_2 116.2(3) . . ?
F3B_2 C19_2 C16_2 111.4(2) . . ?
F2_2 C19_2 C16_2 105.5(3) . . ?
C13_2 C18_2 C17_2 120.82(15) . . ?

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
C5_1 S1_1 C2_1 N1_1 179.11(15) . . . . ?
C5_1 S1_1 C2_1 C3_1 -2.49(13) . . . . ?
N1_1 C2_1 C3_1 C4_1 -179.53(17) . . . . ?
S1_1 C2_1 C3_1 C4_1 2.24(17) . . . . ?
N1_1 C2_1 C3_1 C6_1 0.6(3) . . . . ?
S1_1 C2_1 C3_1 C6_1 -177.66(13) . . . . ?
C19_1 F2_1 F1B_1 F1_1 -22.4(8) . . . . ?
F2B_1 F2_1 F1B_1 F1_1 5.1(10) . . . . ?
F2B_1 F2_1 F1B_1 C19_1 27.5(4) . . . . ?
F3B_1 F1_1 F1B_1 F2_1 8.7(17) . . . . ?
C19_1 F1_1 F1B_1 F2_1 25.3(9) . . . . ?
F3B_1 F1_1 F1B_1 C19_1 -16.7(10) . . . . ?
F3B_1 F3_1 F2B_1 C19_1 12.5(15) . . . . ?
C19_1 F3_1 F2B_1 F2_1 -30.0(14) . . . . ?
F3B_1 F3_1 F2B_1 F2_1 -17(3) . . . . ?
F1B_1 F2_1 F2B_1 F3_1 4(2) . . . . ?
C19_1 F2_1 F2B_1 F3_1 37.3(19) . . . . ?
F1B_1 F2_1 F2B_1 C19_1 -32.8(5) . . . . ?
F1B_1 F1_1 F3B_1 C19_1 14.7(9) . . . . ?
F1B_1 F1_1 F3B_1 F3_1 -17.3(12) . . . . ?
C19_1 F1_1 F3B_1 F3_1 -32.1(4) . . . . ?
F2B_1 F3_1 F3B_1 F1_1 23(2) . . . . ?
C19_1 F3_1 F3B_1 F1_1 37.9(5) . . . . ?
F2B_1 F3_1 F3B_1 C19_1 -15.0(18) . . . . ?
O1_1 C20_1 C5_1 C4_1 168.3(2) . . . . ?
C21_1 C20_1 C5_1 C4_1 -11.8(3) . . . . ?
O1_1 C20_1 C5_1 S1_1 -12.0(2) . . . . ?
C21_1 C20_1 C5_1 S1_1 167.97(15) . . . . ?
C2_1 S1_1 C5_1 C4_1 2.18(14) . . . . ?
C2_1 S1_1 C5_1 C20_1 -177.65(14) . . . . ?
C20_1 C5_1 C4_1 C3_1 178.53(19) . . . . ?
S1_1 C5_1 C4_1 C3_1 -1.26(19) . . . . ?
C20_1 C5_1 C4_1 C13_1 -2.3(3) . . . . ?
S1_1 C5_1 C4_1 C13_1 177.90(12) . . . . ?
C2_1 C3_1 C4_1 C5_1 -0.6(2) . . . . ?
C6_1 C3_1 C4_1 C5_1 179.25(17) . . . . ?
C2_1 C3_1 C4_1 C13_1 -179.77(14) . . . . ?
C6_1 C3_1 C4_1 C13_1 0.1(3) . . . . ?
C25_1 C26_1 C21_1 C22_1 -0.3(3) . . . . ?
C25_1 C26_1 C21_1 C20_1 -176.5(2) . . . . ?
O1_1 C20_1 C21_1 C26_1 119.0(2) . . . . ?
C5_1 C20_1 C21_1 C26_1 -60.9(3) . . . . ?
O1_1 C20_1 C21_1 C22_1 -57.3(3) . . . . ?
C5_1 C20_1 C21_1 C22_1 122.8(2) . . . . ?
C4_1 C3_1 C6_1 O2_1 164.64(19) . . . . ?
C2_1 C3_1 C6_1 O2_1 -15.5(3) . . . . ?
C4_1 C3_1 C6_1 C7_1 -15.1(3) . . . . ?
C2_1 C3_1 C6_1 C7_1 164.81(16) . . . . ?
C26_1 C21_1 C22_1 C23_1 2.3(3) . . . . ?
C20_1 C21_1 C22_1 C23_1 178.7(2) . . . . ?
O2_1 C6_1 C7_1 C12_1 128.5(2) . . . . ?
C3_1 C6_1 C7_1 C12_1 -51.7(3) . . . . ?
O2_1 C6_1 C7_1 C8_1 -47.6(3) . . . . ?
C3_1 C6_1 C7_1 C8_1 132.1(2) . . . . ?
C21_1 C22_1 C23_1 C24_1 -2.4(4) . . . . ?
C12_1 C7_1 C8_1 C9_1 2.6(3) . . . . ?
C6_1 C7_1 C8_1 C9_1 178.9(2) . . . . ?
C22_1 C23_1 C24_1 C25_1 0.4(5) . . . . ?
C7_1 C8_1 C9_1 C10_1 -2.1(4) . . . . ?
C21_1 C26_1 C25_1 C24_1 -1.7(4) . . . . ?
C23_1 C24_1 C25_1 C26_1 1.7(5) . . . . ?
C8_1 C9_1 C10_1 C11_1 0.3(4) . . . . ?
C9_1 C10_1 C11_1 C12_1 1.1(4) . . . . ?
C8_1 C7_1 C12_1 C11_1 -1.2(3) . . . . ?
C6_1 C7_1 C12_1 C11_1 -177.31(19) . . . . ?
C10_1 C11_1 C12_1 C7_1 -0.6(3) . . . . ?
C5_1 C4_1 C13_1 C18_1 -60.5(2) . . . . ?
C3_1 C4_1 C13_1 C18_1 118.57(18) . . . . ?
C5_1 C4_1 C13_1 C14_1 119.46(18) . . . . ?
C3_1 C4_1 C13_1 C14_1 -61.5(2) . . . . ?
C18_1 C13_1 C14_1 C15_1 -0.6(2) . . . . ?
C4_1 C13_1 C14_1 C15_1 179.44(15) . . . . ?
C18_1 C17_1 C16_1 C15_1 0.0(3) . . . . ?
C18_1 C17_1 C16_1 C19_1 -179.3(2) . . . . ?
C13_1 C14_1 C15_1 C16_1 0.3(3) . . . . ?
C17_1 C16_1 C15_1 C14_1 0.0(3) . . . . ?
C19_1 C16_1 C15_1 C14_1 179.3(2) . . . . ?
F2_1 F1B_1 C19_1 F1_1 -162.9(7) . . . . ?
F2_1 F1B_1 C19_1 F2B_1 -44.7(7) . . . . ?
F1_1 F1B_1 C19_1 F2B_1 118.2(6) . . . . ?
F2_1 F1B_1 C19_1 F3_1 -70.5(8) . . . . ?
F1_1 F1B_1 C19_1 F3_1 92.4(7) . . . . ?
F2_1 F1B_1 C19_1 F3B_1 -155.2(6) . . . . ?
F1_1 F1B_1 C19_1 F3B_1 7.7(5) . . . . ?
F1_1 F1B_1 C19_1 F2_1 162.9(7) . . . . ?
F2_1 F1B_1 C19_1 C16_1 90.2(6) . . . . ?
F1_1 F1B_1 C19_1 C16_1 -107.0(4) . . . . ?
F3B_1 F1_1 C19_1 F1B_1 168.9(7) . . . . ?
F3B_1 F1_1 C19_1 F2B_1 70.7(9) . . . . ?
F1B_1 F1_1 C19_1 F2B_1 -98.2(7) . . . . ?
F3B_1 F1_1 C19_1 F3_1 49.5(8) . . . . ?
F1B_1 F1_1 C19_1 F3_1 -119.4(6) . . . . ?
F1B_1 F1_1 C19_1 F3B_1 -168.9(7) . . . . ?
F3B_1 F1_1 C19_1 F2_1 156.8(6) . . . . ?
F1B_1 F1_1 C19_1 F2_1 -12.1(5) . . . . ?
F3B_1 F1_1 C19_1 C16_1 -86.2(6) . . . . ?
F1B_1 F1_1 C19_1 C16_1 104.9(4) . . . . ?
F3_1 F2B_1 C19_1 F1B_1 -121.3(14) . . . . ?
F2_1 F2B_1 C19_1 F1B_1 29.9(5) . . . . ?
F3_1 F2B_1 C19_1 F1_1 -54.4(17) . . . . ?
F2_1 F2B_1 C19_1 F1_1 96.8(7) . . . . ?
F2_1 F2B_1 C19_1 F3_1 151.2(15) . . . . ?
F3_1 F2B_1 C19_1 F3B_1 -12.6(16) . . . . ?
F2_1 F2B_1 C19_1 F3B_1 138.5(4) . . . . ?
F3_1 F2B_1 C19_1 F2_1 -151.2(15) . . . . ?
F3_1 F2B_1 C19_1 C16_1 103.1(14) . . . . ?
F2_1 F2B_1 C19_1 C16_1 -105.7(4) . . . . ?
F2B_1 F3_1 C19_1 F1B_1 71.5(16) . . . . ?
F3B_1 F3_1 C19_1 F1B_1 -96.0(6) . . . . ?
F2B_1 F3_1 C19_1 F1_1 135.5(15) . . . . ?
F3B_1 F3_1 C19_1 F1_1 -32.0(5) . . . . ?
F3B_1 F3_1 C19_1 F2B_1 -167.5(15) . . . . ?
F2B_1 F3_1 C19_1 F3B_1 167.5(15) . . . . ?
F2B_1 F3_1 C19_1 F2_1 29.1(15) . . . . ?
F3B_1 F3_1 C19_1 F2_1 -138.4(4) . . . . ?
F2B_1 F3_1 C19_1 C16_1 -88.9(15) . . . . ?
F3B_1 F3_1 C19_1 C16_1 103.6(4) . . . . ?
F1_1 F3B_1 C19_1 F1B_1 -9.6(6) . . . . ?
F3_1 F3B_1 C19_1 F1B_1 123.5(5) . . . . ?
F3_1 F3B_1 C19_1 F1_1 133.0(7) . . . . ?
F1_1 F3B_1 C19_1 F2B_1 -127.7(7) . . . . ?
F3_1 F3B_1 C19_1 F2B_1 5.4(7) . . . . ?
F1_1 F3B_1 C19_1 F3_1 -133.0(7) . . . . ?
F1_1 F3B_1 C19_1 F2_1 -36.3(9) . . . . ?
F3_1 F3B_1 C19_1 F2_1 96.7(7) . . . . ?
F1_1 F3B_1 C19_1 C16_1 111.6(6) . . . . ?
F3_1 F3B_1 C19_1 C16_1 -115.4(4) . . . . ?
F2B_1 F2_1 C19_1 F1B_1 -139.3(6) . . . . ?
F1B_1 F2_1 C19_1 F1_1 14.8(6) . . . . ?
F2B_1 F2_1 C19_1 F1_1 -124.5(5) . . . . ?
F1B_1 F2_1 C19_1 F2B_1 139.3(6) . . . . ?
F1B_1 F2_1 C19_1 F3_1 127.4(6) . . . . ?
F2B_1 F2_1 C19_1 F3_1 -11.9(7) . . . . ?
F1B_1 F2_1 C19_1 F3B_1 39.2(9) . . . . ?
F2B_1 F2_1 C19_1 F3B_1 -100.1(7) . . . . ?
F1B_1 F2_1 C19_1 C16_1 -108.4(5) . . . . ?
F2B_1 F2_1 C19_1 C16_1 112.3(4) . . . . ?
C17_1 C16_1 C19_1 F1B_1 -167.1(6) . . . . ?
C15_1 C16_1 C19_1 F1B_1 13.6(7) . . . . ?
C17_1 C16_1 C19_1 F1_1 127.2(7) . . . . ?
C15_1 C16_1 C19_1 F1_1 -52.0(8) . . . . ?
C17_1 C16_1 C19_1 F2B_1 -32.3(6) . . . . ?
C15_1 C16_1 C19_1 F2B_1 148.5(5) . . . . ?
C17_1 C16_1 C19_1 F3_1 -5.0(7) . . . . ?
C15_1 C16_1 C19_1 F3_1 175.8(6) . . . . ?
C17_1 C16_1 C19_1 F3B_1 81.7(5) . . . . ?
C15_1 C16_1 C19_1 F3B_1 -97.6(5) . . . . ?
C17_1 C16_1 C19_1 F2_1 -119.8(5) . . . . ?
C15_1 C16_1 C19_1 F2_1 61.0(5) . . . . ?
C16_1 C17_1 C18_1 C13_1 -0.3(3) . . . . ?
C14_1 C13_1 C18_1 C17_1 0.6(3) . . . . ?
C4_1 C13_1 C18_1 C17_1 -179.42(16) . . . . ?
C5_2 S1_2 C2_2 N1_2 -177.87(14) . . . . ?
C5_2 S1_2 C2_2 C3_2 3.78(12) . . . . ?
F3B_2 F1_2 F1B_2 C19_2 27.8(12) . . . . ?
C19_2 F1_2 F1B_2 F2_2 -14.8(14) . . . . ?
F3B_2 F1_2 F1B_2 F2_2 13(3) . . . . ?
F2B_2 F2_2 F1B_2 F1_2 -20.3(19) . . . . ?
C19_2 F2_2 F1B_2 F1_2 17.4(17) . . . . ?
F2B_2 F2_2 F1B_2 C19_2 -37.7(3) . . . . ?
C19_2 F2_2 F2B_2 F3_2 -11.3(6) . . . . ?
F1B_2 F2_2 F2B_2 F3_2 21.1(7) . . . . ?
F1B_2 F2_2 F2B_2 C19_2 32.3(3) . . . . ?
F3B_2 F3_2 F2B_2 F2_2 -20.6(10) . . . . ?
C19_2 F3_2 F2B_2 F2_2 12.3(6) . . . . ?
F3B_2 F3_2 F2B_2 C19_2 -32.9(5) . . . . ?
F2B_2 F3_2 F3B_2 C19_2 31.1(5) . . . . ?
F2B_2 F3_2 F3B_2 F1_2 5.7(7) . . . . ?
C19_2 F3_2 F3B_2 F1_2 -25.4(4) . . . . ?
F1B_2 F1_2 F3B_2 F3_2 -4.8(19) . . . . ?
C19_2 F1_2 F3B_2 F3_2 28.7(4) . . . . ?
F1B_2 F1_2 F3B_2 C19_2 -33.6(16) . . . . ?
N1_2 C2_2 C3_2 C4_2 178.59(16) . . . . ?
S1_2 C2_2 C3_2 C4_2 -3.26(17) . . . . ?
N1_2 C2_2 C3_2 C6_2 -3.2(3) . . . . ?
S1_2 C2_2 C3_2 C6_2 174.94(12) . . . . ?
O1_2 C20_2 C5_2 C4_2 -161.71(18) . . . . ?
C21_2 C20_2 C5_2 C4_2 18.9(3) . . . . ?
O1_2 C20_2 C5_2 S1_2 17.2(2) . . . . ?
C21_2 C20_2 C5_2 S1_2 -162.25(13) . . . . ?
C2_2 S1_2 C5_2 C4_2 -3.43(13) . . . . ?
C2_2 S1_2 C5_2 C20_2 177.45(13) . . . . ?
C20_2 C5_2 C4_2 C3_2 -178.95(17) . . . . ?
S1_2 C5_2 C4_2 C3_2 2.17(17) . . . . ?
C20_2 C5_2 C4_2 C13_2 1.9(3) . . . . ?
S1_2 C5_2 C4_2 C13_2 -177.00(11) . . . . ?
C2_2 C3_2 C4_2 C5_2 0.69(19) . . . . ?
C6_2 C3_2 C4_2 C5_2 -177.28(15) . . . . ?
C2_2 C3_2 C4_2 C13_2 179.83(14) . . . . ?
C6_2 C3_2 C4_2 C13_2 1.9(3) . . . . ?
C25_2 C26_2 C21_2 C22_2 1.2(3) . . . . ?
C25_2 C26_2 C21_2 C20_2 -179.70(18) . . . . ?
O1_2 C20_2 C21_2 C26_2 -131.66(19) . . . . ?
C5_2 C20_2 C21_2 C26_2 47.7(2) . . . . ?
O1_2 C20_2 C21_2 C22_2 47.4(2) . . . . ?
C5_2 C20_2 C21_2 C22_2 -133.18(18) . . . . ?
C2_2 C3_2 C6_2 O2_2 24.7(2) . . . . ?
C4_2 C3_2 C6_2 O2_2 -157.49(16) . . . . ?
C2_2 C3_2 C6_2 C7_2 -152.35(15) . . . . ?
C4_2 C3_2 C6_2 C7_2 25.5(3) . . . . ?
C26_2 C21_2 C22_2 C23_2 -2.4(3) . . . . ?
C20_2 C21_2 C22_2 C23_2 178.5(2) . . . . ?
O2_2 C6_2 C7_2 C8_2 -137.77(18) . . . . ?
C3_2 C6_2 C7_2 C8_2 39.3(2) . . . . ?
O2_2 C6_2 C7_2 C12_2 38.5(3) . . . . ?
C3_2 C6_2 C7_2 C12_2 -144.45(19) . . . . ?
C21_2 C22_2 C23_2 C24_2 1.4(4) . . . . ?
C12_2 C7_2 C8_2 C9_2 0.9(3) . . . . ?
C6_2 C7_2 C8_2 C9_2 177.15(19) . . . . ?
C22_2 C23_2 C24_2 C25_2 0.8(4) . . . . ?
C7_2 C8_2 C9_2 C10_2 0.2(4) . . . . ?
C23_2 C24_2 C25_2 C26_2 -2.0(4) . . . . ?
C21_2 C26_2 C25_2 C24_2 1.0(3) . . . . ?
C8_2 C9_2 C10_2 C11_2 -0.8(5) . . . . ?
C9_2 C10_2 C11_2 C12_2 0.2(5) . . . . ?
C10_2 C11_2 C12_2 C7_2 1.0(5) . . . . ?
C8_2 C7_2 C12_2 C11_2 -1.5(4) . . . . ?
C6_2 C7_2 C12_2 C11_2 -177.9(2) . . . . ?
C5_2 C4_2 C13_2 C18_2 -123.01(17) . . . . ?
C3_2 C4_2 C13_2 C18_2 57.9(2) . . . . ?
C5_2 C4_2 C13_2 C14_2 56.4(2) . . . . ?
C3_2 C4_2 C13_2 C14_2 -122.66(17) . . . . ?
C18_2 C13_2 C14_2 C15_2 1.3(3) . . . . ?
C4_2 C13_2 C14_2 C15_2 -178.14(16) . . . . ?
C13_2 C14_2 C15_2 C16_2 0.3(3) . . . . ?
C14_2 C15_2 C16_2 C17_2 -1.3(3) . . . . ?
C14_2 C15_2 C16_2 C19_2 177.69(19) . . . . ?
C15_2 C16_2 C17_2 C18_2 0.7(3) . . . . ?
C19_2 C16_2 C17_2 C18_2 -178.28(19) . . . . ?
F3B_2 F3_2 C19_2 F1_2 37.9(6) . . . . ?
F2B_2 F3_2 C19_2 F1_2 -117.3(6) . . . . ?
F3B_2 F3_2 C19_2 F2B_2 155.2(5) . . . . ?
F3B_2 F3_2 C19_2 F1B_2 66.4(7) . . . . ?
F2B_2 F3_2 C19_2 F1B_2 -88.8(7) . . . . ?
F2B_2 F3_2 C19_2 F3B_2 -155.2(5) . . . . ?
F3B_2 F3_2 C19_2 F2_2 147.5(4) . . . . ?
F2B_2 F3_2 C19_2 F2_2 -7.7(4) . . . . ?
F3B_2 F3_2 C19_2 C16_2 -99.0(4) . . . . ?
F2B_2 F3_2 C19_2 C16_2 105.8(4) . . . . ?
F1B_2 F1_2 C19_2 F3_2 124.5(12) . . . . ?
F3B_2 F1_2 C19_2 F3_2 -28.8(5) . . . . ?
F1B_2 F1_2 C19_2 F2B_2 60.3(14) . . . . ?
F3B_2 F1_2 C19_2 F2B_2 -93.0(5) . . . . ?
F3B_2 F1_2 C19_2 F1B_2 -153.3(14) . . . . ?
F1B_2 F1_2 C19_2 F3B_2 153.3(14) . . . . ?
F1B_2 F1_2 C19_2 F2_2 13.7(14) . . . . ?
F3B_2 F1_2 C19_2 F2_2 -139.7(3) . . . . ?
F1B_2 F1_2 C19_2 C16_2 -99.3(13) . . . . ?
F3B_2 F1_2 C19_2 C16_2 107.4(3) . . . . ?
F2_2 F2B_2 C19_2 F3_2 -170.0(6) . . . . ?
F2_2 F2B_2 C19_2 F1_2 -70.8(6) . . . . ?
F3_2 F2B_2 C19_2 F1_2 99.2(6) . . . . ?
F2_2 F2B_2 C19_2 F1B_2 -46.1(5) . . . . ?
F3_2 F2B_2 C19_2 F1B_2 123.9(5) . . . . ?
F2_2 F2B_2 C19_2 F3B_2 -151.1(4) . . . . ?
F3_2 F2B_2 C19_2 F3B_2 18.9(4) . . . . ?
F3_2 F2B_2 C19_2 F2_2 170.0(6) . . . . ?
F2_2 F2B_2 C19_2 C16_2 88.7(4) . . . . ?
F3_2 F2B_2 C19_2 C16_2 -101.3(4) . . . . ?
F1_2 F1B_2 C19_2 F3_2 -71.3(15) . . . . ?
F2_2 F1B_2 C19_2 F3_2 94.8(6) . . . . ?
F2_2 F1B_2 C19_2 F1_2 166.1(14) . . . . ?
F1_2 F1B_2 C19_2 F2B_2 -131.7(13) . . . . ?
F2_2 F1B_2 C19_2 F2B_2 34.4(3) . . . . ?
F1_2 F1B_2 C19_2 F3B_2 -26.2(14) . . . . ?
F2_2 F1B_2 C19_2 F3B_2 139.9(3) . . . . ?
F1_2 F1B_2 C19_2 F2_2 -166.1(14) . . . . ?
F1_2 F1B_2 C19_2 C16_2 93.7(13) . . . . ?
F2_2 F1B_2 C19_2 C16_2 -100.2(3) . . . . ?
F1_2 F3B_2 C19_2 F3_2 145.6(5) . . . . ?
F3_2 F3B_2 C19_2 F1_2 -145.6(5) . . . . ?
F3_2 F3B_2 C19_2 F2B_2 -20.3(4) . . . . ?
F1_2 F3B_2 C19_2 F2B_2 125.3(5) . . . . ?
F3_2 F3B_2 C19_2 F1B_2 -133.7(5) . . . . ?
F1_2 F3B_2 C19_2 F1B_2 11.8(6) . . . . ?
F3_2 F3B_2 C19_2 F2_2 -55.4(7) . . . . ?
F1_2 F3B_2 C19_2 F2_2 90.1(6) . . . . ?
F3_2 F3B_2 C19_2 C16_2 102.9(4) . . . . ?
F1_2 F3B_2 C19_2 C16_2 -111.5(5) . . . . ?
F2B_2 F2_2 C19_2 F3_2 8.3(5) . . . . ?
F1B_2 F2_2 C19_2 F3_2 -127.4(4) . . . . ?
F2B_2 F2_2 C19_2 F1_2 129.4(5) . . . . ?
F1B_2 F2_2 C19_2 F1_2 -6.3(6) . . . . ?
F1B_2 F2_2 C19_2 F2B_2 -135.7(4) . . . . ?
F2B_2 F2_2 C19_2 F1B_2 135.7(4) . . . . ?
F2B_2 F2_2 C19_2 F3B_2 48.4(7) . . . . ?
F1B_2 F2_2 C19_2 F3B_2 -87.3(6) . . . . ?
F2B_2 F2_2 C19_2 C16_2 -110.8(4) . . . . ?
F1B_2 F2_2 C19_2 C16_2 113.5(3) . . . . ?
C15_2 C16_2 C19_2 F3_2 -13.5(6) . . . . ?
C17_2 C16_2 C19_2 F3_2 165.5(6) . . . . ?
C15_2 C16_2 C19_2 F1_2 -151.3(4) . . . . ?
C17_2 C16_2 C19_2 F1_2 27.7(5) . . . . ?
C15_2 C16_2 C19_2 F2B_2 46.8(5) . . . . ?
C17_2 C16_2 C19_2 F2B_2 -134.2(5) . . . . ?
C15_2 C16_2 C19_2 F1B_2 179.1(4) . . . . ?
C17_2 C16_2 C19_2 F1B_2 -1.9(5) . . . . ?
C15_2 C16_2 C19_2 F3B_2 -67.4(4) . . . . ?
C17_2 C16_2 C19_2 F3B_2 111.6(3) . . . . ?
C15_2 C16_2 C19_2 F2_2 98.5(3) . . . . ?
C17_2 C16_2 C19_2 F2_2 -82.5(4) . . . . ?
C14_2 C13_2 C18_2 C17_2 -1.9(2) . . . . ?
C4_2 C13_2 C18_2 C17_2 177.51(15) . . . . ?
C16_2 C17_2 C18_2 C13_2 0.9(3) . . . . ?

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
N1_1 H1N1_1 O2_1 0.911(16) 2.05(2) 2.662(2) 123(2) . yes
N1_1 H1N1_1 O2_2 0.911(16) 2.209(19) 3.031(2) 150(2) 4_556 yes
N1_1 H1N2_1 O1_2 0.917(15) 2.001(17) 2.869(2) 157(2) . yes
N1_2 H1N1_2 O1_1 0.900(14) 2.030(15) 2.899(2) 161.9(17) 1_545 yes
N1_2 H1N2_2 O2_1 0.878(15) 2.188(17) 2.982(2) 150.3(19) 4 yes
N1_2 H1N2_2 O2_2 0.878(15) 2.135(19) 2.7305(19) 124.5(18) . yes

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.036



_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_NTT009F4
_database_code_depnum_ccdc_archive 'CCDC 2165840'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-04-15 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT430_NTT009F4            
;
PROBLEM: Short Inter D...A Contact  O1_2     ..O1_3     .       2.78 Ang.  
RESPONSE: This is the case when  short C=O..O=C contacts are part of multi-centre
 bridging involving in this case a R2,2(12) graph-set synthon with NH2 and C=O.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
;
'(5-amino-4-benzoyl-3-(4-methoxyphenyl)thiophen-2-yl)(4-methoxyphenyl)methanone'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H21 N O4 S'
_chemical_formula_sum            'C26 H21 N O4 S'
_chemical_formula_weight         443.50

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'

_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                   12.63107(19)
_cell_length_b                   9.75808(18)
_cell_length_c                   54.9229(7)
_cell_angle_alpha                90.0
_cell_angle_beta                 95.3721(14)
_cell_angle_gamma                90.0
_cell_volume                     6739.79(18)
_cell_formula_units_Z            12.00
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    41835
_cell_measurement_theta_min      2.1540
_cell_measurement_theta_max      28.3810

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.051
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             2784.000
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 2 0.0243
1 0 -2 0.0270
-1 -1 -5 0.0933
0 1 5 0.0606
-1 2 5 0.0650
0 0 1 0.0497
0 0 -1 0.0797
2 -3 5 0.0846
0 -1 -5 0.0835
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_min  0.590
_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_ambient_environment      air
_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            75512
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -67
_diffrn_reflns_limit_l_max       67
_diffrn_reflns_theta_min         2.120
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             13254
_reflns_number_gt                10650
_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    ?
_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)+(0.0515P)²+1.9356P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13247
_refine_ls_number_parameters     895
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.002
_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_1 S 0.21858(4) 0.72023(5) 0.55768(2) 0.04955(13) Uani 1 1 d . . . . .
O1_1 O 0.01004(11) 0.85764(15) 0.49109(2) 0.0638(4) Uani 1 1 d . . . . .
N1_1 N 0.08053(13) 0.90479(16) 0.53895(3) 0.0492(4) Uani 1 1 d D . . . .
H1N1_1 H 0.0435(15) 0.943(2) 0.5267(3) 0.061(6) Uiso 1 1 d D . . . .
H1N2_1 H 0.0937(15) 0.9504(19) 0.5528(3) 0.060(6) Uiso 1 1 d D . . . .
C2_1 C 0.13691(13) 0.79452(17) 0.53446(3) 0.0404(4) Uani 1 1 d . . . . .
O2_1 O 0.26913(12) 0.21484(17) 0.44216(3) 0.0767(5) Uani 1 1 d . . . . .
C3_1 C 0.14302(13) 0.72576(17) 0.51203(3) 0.0391(4) Uani 1 1 d . . . . .
O3_1 O 0.36539(12) 0.51234(15) 0.57155(2) 0.0653(4) Uani 1 1 d . . . . .
C4_1 C 0.20947(12) 0.60715(17) 0.51471(3) 0.0382(4) Uani 1 1 d . . . . .
O4_1 O 0.36505(12) -0.04856(15) 0.51413(3) 0.0702(4) Uani 1 1 d . . . . .
C5_1 C 0.25388(14) 0.58815(18) 0.53842(3) 0.0436(4) Uani 1 1 d . . . . .
C6_1 C 0.08763(13) 0.78252(18) 0.48980(3) 0.0433(4) Uani 1 1 d . . . . .
C7_1 C 0.12474(14) 0.75815(18) 0.46520(3) 0.0443(4) Uani 1 1 d . . . . .
C8_1 C 0.05033(16) 0.7307(2) 0.44580(3) 0.0616(5) Uani 1 1 d . . . . .
H8_1 H -0.021398 0.726212 0.448300 0.074 Uiso 1 1 calc R U . . .
C9_1 C 0.08180(19) 0.7099(3) 0.42270(4) 0.0790(7) Uani 1 1 d . . . . .
H9_1 H 0.031685 0.688092 0.409787 0.095 Uiso 1 1 calc R U . . .
C10_1 C 0.1868(2) 0.7213(3) 0.41882(4) 0.0821(8) Uani 1 1 d . . . . .
H10_1 H 0.208119 0.707330 0.403251 0.098 Uiso 1 1 calc R U . . .
C11_1 C 0.26041(17) 0.7533(3) 0.43773(4) 0.0740(7) Uani 1 1 d . . . . .
H11_1 H 0.331431 0.763394 0.434896 0.089 Uiso 1 1 calc R U . . .
C12_1 C 0.23048(15) 0.7706(2) 0.46093(4) 0.0561(5) Uani 1 1 d . . . . .
H12_1 H 0.281359 0.790694 0.473785 0.067 Uiso 1 1 calc R U . . .
C13_1 C 0.22437(13) 0.51083(17) 0.49439(3) 0.0385(4) Uani 1 1 d . . . . .
C14_1 C 0.13809(14) 0.44489(19) 0.48250(3) 0.0475(4) Uani 1 1 d . . . . .
H14_1 H 0.070258 0.467496 0.486460 0.057 Uiso 1 1 calc R U . . .
C15_1 C 0.14905(15) 0.3462(2) 0.46488(3) 0.0537(5) Uani 1 1 d . . . . .
H15_1 H 0.089560 0.301910 0.457344 0.064 Uiso 1 1 calc R U . . .
C16_1 C 0.24906(15) 0.3144(2) 0.45863(3) 0.0520(5) Uani 1 1 d . . . . .
C17_1 C 0.33650(15) 0.3847(2) 0.46934(3) 0.0524(5) Uani 1 1 d . . . . .
H17_1 H 0.403628 0.367162 0.464395 0.063 Uiso 1 1 calc R U . . .
C18_1 C 0.32452(13) 0.48035(18) 0.48729(3) 0.0442(4) Uani 1 1 d . . . . .
H18_1 H 0.384009 0.525071 0.494738 0.053 Uiso 1 1 calc R U . . .
C19_1 C 0.1833(2) 0.1282(3) 0.43361(5) 0.0858(8) Uani 1 1 d . . . . .
H19A_1 H 0.131872 0.179932 0.423440 0.129 Uiso 1 1 calc R U . . .
H19B_1 H 0.150610 0.091642 0.447301 0.129 Uiso 1 1 calc R U . . .
H19C_1 H 0.209494 0.054305 0.424301 0.129 Uiso 1 1 calc R U . . .
C20_1 C 0.32093(14) 0.48446(19) 0.55107(3) 0.0473(4) Uani 1 1 d . . . . .
C21_1 C 0.33349(14) 0.34567(19) 0.54083(3) 0.0445(4) Uani 1 1 d . . . . .
C22_1 C 0.24850(14) 0.2724(2) 0.52941(3) 0.0504(4) Uani 1 1 d . . . . .
H22_1 H 0.181520 0.312737 0.527549 0.060 Uiso 1 1 calc R U . . .
C23_1 C 0.26104(15) 0.1423(2) 0.52084(4) 0.0543(5) Uani 1 1 d . . . . .
H23_1 H 0.203214 0.095567 0.513088 0.065 Uiso 1 1 calc R U . . .
C24_1 C 0.35970(15) 0.08073(19) 0.52374(3) 0.0500(4) Uani 1 1 d . . . . .
C25_1 C 0.44560(15) 0.1504(2) 0.53510(3) 0.0529(5) Uani 1 1 d . . . . .
H25_1 H 0.512273 0.109276 0.536985 0.064 Uiso 1 1 calc R U . . .
C26_1 C 0.43193(15) 0.2818(2) 0.54364(3) 0.0517(5) Uani 1 1 d . . . . .
H26_1 H 0.489846 0.328214 0.551427 0.062 Uiso 1 1 calc R U . . .
C27_1 C 0.45023(18) -0.1347(2) 0.52283(4) 0.0658(6) Uani 1 1 d . . . . .
H27A_1 H 0.442588 -0.222132 0.514842 0.099 Uiso 1 1 calc R U . . .
H27B_1 H 0.449692 -0.146914 0.540164 0.099 Uiso 1 1 calc R U . . .
H27C_1 H 0.516274 -0.093633 0.519401 0.099 Uiso 1 1 calc R U . . .
O1_2 O 0.80715(14) 0.43351(15) 0.33373(2) 0.0703(4) Uani 1 1 d . . . . .
S1_2 S 0.78177(4) 0.70238(5) 0.39967(2) 0.04934(12) Uani 1 1 d . . . . .
N1_2 N 0.72628(14) 0.46533(19) 0.37878(3) 0.0561(4) Uani 1 1 d D . . . .
H1N1_2 H 0.7256(18) 0.403(2) 0.3672(4) 0.078(7) Uiso 1 1 d D . . . .
H1N2_2 H 0.6989(15) 0.450(2) 0.3925(3) 0.059(6) Uiso 1 1 d D . . . .
O2_2 O 1.02640(13) 1.08779(16) 0.28586(3) 0.0774(5) Uani 1 1 d . . . . .
C2_2 C 0.77161(14) 0.58700(19) 0.37586(3) 0.0445(4) Uani 1 1 d . . . . .
O3_2 O 0.84638(11) 0.96329(15) 0.41595(2) 0.0600(4) Uani 1 1 d . . . . .
C3_2 C 0.81082(13) 0.64117(18) 0.35467(3) 0.0426(4) Uani 1 1 d . . . . .
O4_2 O 1.14680(13) 1.32112(18) 0.35447(3) 0.0863(5) Uani 1 1 d . . . . .
C5_2 C 0.84704(13) 0.82036(19) 0.38247(3) 0.0437(4) Uani 1 1 d . . . . .
C6_2 C 0.80457(14) 0.5591(2) 0.33217(3) 0.0479(4) Uani 1 1 d . . . . .
C7_2 C 0.79326(14) 0.6220(2) 0.30736(3) 0.0476(4) Uani 1 1 d . . . . .
C8_2 C 0.73306(15) 0.7373(2) 0.30169(4) 0.0605(5) Uani 1 1 d . . . . .
H8_2 H 0.699044 0.781437 0.313775 0.073 Uiso 1 1 calc R U . . .
C9_2 C 0.7232(2) 0.7873(3) 0.27806(4) 0.0839(7) Uani 1 1 d . . . . .
H9_2 H 0.682039 0.864746 0.274208 0.101 Uiso 1 1 calc R U . . .
C10_2 C 0.7739(3) 0.7229(3) 0.26037(4) 0.0939(9) Uani 1 1 d . . . . .
H10_2 H 0.767710 0.757404 0.244521 0.113 Uiso 1 1 calc R U . . .
C11_2 C 0.8334(3) 0.6086(3) 0.26575(4) 0.0884(8) Uani 1 1 d . . . . .
H11_2 H 0.867919 0.565558 0.253615 0.106 Uiso 1 1 calc R U . . .
C12_2 C 0.84230(19) 0.5570(2) 0.28907(4) 0.0664(6) Uani 1 1 d . . . . .
H12_2 H 0.881631 0.477736 0.292610 0.080 Uiso 1 1 calc R U . . .
C13_2 C 0.89909(13) 0.85831(18) 0.33963(3) 0.0409(4) Uani 1 1 d . . . . .
C14_2 C 0.98077(13) 0.80947(19) 0.32666(3) 0.0458(4) Uani 1 1 d . . . . .
H14_2 H 1.008358 0.722402 0.330001 0.055 Uiso 1 1 calc R U . . .
C15_2 C 1.02108(15) 0.8881(2) 0.30902(3) 0.0529(5) Uani 1 1 d . . . . .
H15_2 H 1.075794 0.854072 0.300542 0.063 Uiso 1 1 calc R U . . .
C16_2 C 0.98100(15) 1.0176(2) 0.30374(3) 0.0526(5) Uani 1 1 d . . . . .
C17_2 C 0.89963(15) 1.0683(2) 0.31638(3) 0.0515(4) Uani 1 1 d . . . . .
H17_2 H 0.872231 1.155428 0.312999 0.062 Uiso 1 1 calc R U . . .
C18_2 C 0.85980(14) 0.98821(19) 0.33402(3) 0.0468(4) Uani 1 1 d . . . . .
H18_2 H 0.804865 1.022282 0.342421 0.056 Uiso 1 1 calc R U . . .
C19_2 C 0.9892(2) 1.2230(3) 0.28075(5) 0.0882(8) Uani 1 1 d . . . . .
H19A_2 H 1.001782 1.278301 0.295184 0.132 Uiso 1 1 calc R U . . .
H19B_2 H 0.914362 1.220610 0.275724 0.132 Uiso 1 1 calc R U . . .
H19C_2 H 1.026322 1.261426 0.267889 0.132 Uiso 1 1 calc R U . . .
C20_2 C 0.88221(14) 0.94268(19) 0.39607(3) 0.0465(4) Uani 1 1 d . . . . .
C21_2 C 0.95638(14) 1.04197(19) 0.38650(3) 0.0468(4) Uani 1 1 d . . . . .
C22_2 C 1.04888(14) 1.0027(2) 0.37633(3) 0.0494(4) Uani 1 1 d . . . . .
H22_2 H 1.068534 0.910833 0.376409 0.059 Uiso 1 1 calc R U . . .
C23_2 C 1.11107(15) 1.0986(2) 0.36621(4) 0.0560(5) Uani 1 1 d . . . . .
H23_2 H 1.172831 1.071556 0.359558 0.067 Uiso 1 1 calc R U . . .
C24_2 C 1.08212(16) 1.2350(2) 0.36590(4) 0.0604(5) Uani 1 1 d . . . . .
C25_2 C 0.99231(17) 1.2764(2) 0.37653(4) 0.0645(6) Uani 1 1 d . . . . .
H25_2 H 0.973466 1.368505 0.376652 0.077 Uiso 1 1 calc R U . . .
C26_2 C 0.93120(16) 1.1797(2) 0.38691(4) 0.0566(5) Uani 1 1 d . . . . .
H26_2 H 0.871680 1.207689 0.394370 0.068 Uiso 1 1 calc R U . . .
C27_2 C 1.1122(3) 1.4584(3) 0.35018(6) 0.1016(9) Uani 1 1 d . . . . .
H27A_2 H 1.108333 1.504237 0.365540 0.152 Uiso 1 1 calc R U . . .
H27B_2 H 1.043185 1.458207 0.341217 0.152 Uiso 1 1 calc R U . . .
H27C_2 H 1.161662 1.505473 0.340890 0.152 Uiso 1 1 calc R U . . .
C4_2 C 0.85387(13) 0.77549(18) 0.35880(3) 0.0413(4) Uani 1 1 d . . . . .
S1_3 S 0.51960(4) 1.11434(5) 0.27157(2) 0.05172(13) Uani 1 1 d . . . . .
O2_3 O 0.33398(12) 0.60055(16) 0.37609(3) 0.0720(4) Uani 1 1 d . . . . .
C2_3 C 0.58253(14) 1.17680(19) 0.29847(3) 0.0445(4) Uani 1 1 d . . . . .
O3_3 O 0.38195(12) 0.92274(15) 0.24893(2) 0.0669(4) Uani 1 1 d . . . . .
C3_3 C 0.55476(13) 1.10226(18) 0.31902(3) 0.0405(4) Uani 1 1 d . . . . .
O4_3 O 0.22690(12) 0.38314(15) 0.29576(3) 0.0701(4) Uani 1 1 d . . . . .
C5_3 C 0.46142(14) 0.98181(19) 0.28699(3) 0.0453(4) Uani 1 1 d . . . . .
C6_3 C 0.59427(14) 1.14837(18) 0.34339(3) 0.0430(4) Uani 1 1 d . . . . .
C7_3 C 0.54282(13) 1.11271(18) 0.36584(3) 0.0425(4) Uani 1 1 d . . . . .
C8_3 C 0.43555(15) 1.1279(2) 0.36760(3) 0.0597(5) Uani 1 1 d . . . . .
H8_3 H 0.390951 1.154581 0.353991 0.072 Uiso 1 1 calc R U . . .
C9_3 C 0.39438(18) 1.1036(3) 0.38943(4) 0.0885(9) Uani 1 1 d . . . . .
H9_3 H 0.322351 1.117812 0.390770 0.106 Uiso 1 1 calc R U . . .
C10_3 C 0.45873(19) 1.0587(3) 0.40925(4) 0.0908(9) Uani 1 1 d . . . . .
H10_3 H 0.429828 1.039652 0.423844 0.109 Uiso 1 1 calc R U . . .
C11_3 C 0.56546(18) 1.0417(3) 0.40770(4) 0.0786(7) Uani 1 1 d . . . . .
H11_3 H 0.609047 1.010187 0.421122 0.094 Uiso 1 1 calc R U . . .
C12_3 C 0.60753(15) 1.0714(2) 0.38622(3) 0.0584(5) Uani 1 1 d . . . . .
H12_3 H 0.680454 1.063793 0.385333 0.070 Uiso 1 1 calc R U . . .
C13_3 C 0.44723(13) 0.88991(17) 0.32962(3) 0.0398(4) Uani 1 1 d . . . . .
C14_3 C 0.33900(13) 0.86742(18) 0.33091(3) 0.0446(4) Uani 1 1 d . . . . .
H14_3 H 0.289639 0.917786 0.320965 0.053 Uiso 1 1 calc R U . . .
C15_3 C 0.30446(14) 0.77220(19) 0.34663(3) 0.0489(4) Uani 1 1 d . . . . .
H15_3 H 0.231893 0.759087 0.347355 0.059 Uiso 1 1 calc R U . . .
C16_3 C 0.37641(15) 0.69505(19) 0.36147(3) 0.0496(4) Uani 1 1 d . . . . .
C17_3 C 0.48408(14) 0.7180(2) 0.36089(3) 0.0511(4) Uani 1 1 d . . . . .
H17_3 H 0.533268 0.668212 0.370986 0.061 Uiso 1 1 calc R U . . .
C18_3 C 0.51778(13) 0.81543(19) 0.34517(3) 0.0453(4) Uani 1 1 d . . . . .
H18_3 H 0.590281 0.831563 0.345025 0.054 Uiso 1 1 calc R U . . .
C19_3 C 0.4045(2) 0.5137(3) 0.39088(6) 0.1005(9) Uani 1 1 d . . . . .
H19A_3 H 0.452351 0.568768 0.401368 0.151 Uiso 1 1 calc R U . . .
H19B_3 H 0.444396 0.458203 0.380569 0.151 Uiso 1 1 calc R U . . .
H19C_3 H 0.364048 0.455567 0.400658 0.151 Uiso 1 1 calc R U . . .
C20_3 C 0.39995(15) 0.8881(2) 0.27057(3) 0.0491(4) Uani 1 1 d . . . . .
C21_3 C 0.35922(14) 0.75479(19) 0.27843(3) 0.0465(4) Uani 1 1 d . . . . .
C22_3 C 0.25353(16) 0.7220(2) 0.27155(4) 0.0584(5) Uani 1 1 d . . . . .
H22_3 H 0.210352 0.784850 0.262596 0.070 Uiso 1 1 calc R U . . .
C23_3 C 0.21201(16) 0.5983(2) 0.27778(4) 0.0637(6) Uani 1 1 d . . . . .
H23_3 H 0.140611 0.578901 0.273499 0.076 Uiso 1 1 calc R U . . .
C24_3 C 0.27646(16) 0.5025(2) 0.29045(3) 0.0537(5) Uani 1 1 d . . . . .
C25_3 C 0.38242(15) 0.5308(2) 0.29657(3) 0.0543(5) Uani 1 1 d . . . . .
H25_3 H 0.426587 0.465402 0.304537 0.065 Uiso 1 1 calc R U . . .
C26_3 C 0.42261(15) 0.6570(2) 0.29079(3) 0.0518(5) Uani 1 1 d . . . . .
H26_3 H 0.493794 0.676657 0.295312 0.062 Uiso 1 1 calc R U . . .
C27_3 C 0.2882(2) 0.2796(3) 0.30872(5) 0.0862(8) Uani 1 1 d . . . . .
H27A_3 H 0.315395 0.314019 0.324442 0.129 Uiso 1 1 calc R U . . .
H27B_3 H 0.346346 0.253746 0.299617 0.129 Uiso 1 1 calc R U . . .
H27C_3 H 0.244181 0.201046 0.310827 0.129 Uiso 1 1 calc R U . . .
C4_3 C 0.48573(13) 0.98967(18) 0.31208(3) 0.0404(4) Uani 1 1 d . . . . .
O1_3 O 0.67363(11) 1.22259(15) 0.34593(2) 0.0624(4) Uani 1 1 d . . . . .
N1_3 N 0.64577(14) 1.28513(18) 0.29803(3) 0.0562(4) Uani 1 1 d D . . . .
H1N1_3 H 0.6472(16) 1.329(2) 0.2842(3) 0.065(6) Uiso 1 1 d D . . . .
H1N2_3 H 0.6822(15) 1.311(2) 0.3117(3) 0.060(6) Uiso 1 1 d 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
S1_1 C2_1 1.7233(17) . ?
S1_1 C5_1 1.7513(17) . ?
O1_1 C6_1 1.231(2) . ?
N1_1 C2_1 1.326(2) . ?
N1_1 H1N1_1 0.870(14) . ?
N1_1 H1N2_1 0.884(14) . ?
C2_1 C3_1 1.411(2) . ?
O2_1 C16_1 1.367(2) . ?
O2_1 C19_1 1.420(3) . ?
C3_1 C4_1 1.429(2) . ?
C3_1 C6_1 1.458(2) . ?
O3_1 C20_1 1.239(2) . ?
C4_1 C5_1 1.381(2) . ?
C4_1 C13_1 1.485(2) . ?
O4_1 C24_1 1.372(2) . ?
O4_1 C27_1 1.413(2) . ?
C5_1 C20_1 1.454(2) . ?
C6_1 C7_1 1.490(2) . ?
C7_1 C8_1 1.379(2) . ?
C7_1 C12_1 1.383(3) . ?
C8_1 C9_1 1.379(3) . ?
C8_1 H8_1 0.9300 . ?
C9_1 C10_1 1.368(3) . ?
C9_1 H9_1 0.9300 . ?
C10_1 C11_1 1.363(3) . ?
C10_1 H10_1 0.9300 . ?
C11_1 C12_1 1.373(3) . ?
C11_1 H11_1 0.9300 . ?
C12_1 H12_1 0.9300 . ?
C13_1 C14_1 1.376(2) . ?
C13_1 C18_1 1.390(2) . ?
C14_1 C15_1 1.381(2) . ?
C14_1 H14_1 0.9300 . ?
C15_1 C16_1 1.375(3) . ?
C15_1 H15_1 0.9300 . ?
C16_1 C17_1 1.384(3) . ?
C17_1 C18_1 1.376(2) . ?
C17_1 H17_1 0.9300 . ?
C18_1 H18_1 0.9300 . ?
C19_1 H19A_1 0.9600 . ?
C19_1 H19B_1 0.9600 . ?
C19_1 H19C_1 0.9600 . ?
C20_1 C21_1 1.481(3) . ?
C21_1 C26_1 1.387(2) . ?
C21_1 C22_1 1.389(3) . ?
C22_1 C23_1 1.368(3) . ?
C22_1 H22_1 0.9300 . ?
C23_1 C24_1 1.379(3) . ?
C23_1 H23_1 0.9300 . ?
C24_1 C25_1 1.379(3) . ?
C25_1 C26_1 1.381(3) . ?
C25_1 H25_1 0.9300 . ?
C26_1 H26_1 0.9300 . ?
C27_1 H27A_1 0.9600 . ?
C27_1 H27B_1 0.9600 . ?
C27_1 H27C_1 0.9600 . ?
O1_2 C6_2 1.229(2) . ?
S1_2 C2_2 1.7211(18) . ?
S1_2 C5_2 1.7446(18) . ?
N1_2 C2_2 1.334(2) . ?
N1_2 H1N1_2 0.880(15) . ?
N1_2 H1N2_2 0.870(14) . ?
O2_2 C16_2 1.366(2) . ?
O2_2 C19_2 1.419(3) . ?
C2_2 C3_2 1.410(2) . ?
O3_2 C20_2 1.237(2) . ?
C3_2 C4_2 1.429(2) . ?
C3_2 C6_2 1.468(2) . ?
O4_2 C24_2 1.365(3) . ?
O4_2 C27_2 1.422(3) . ?
C5_2 C4_2 1.382(2) . ?
C5_2 C20_2 1.455(2) . ?
C6_2 C7_2 1.489(2) . ?
C7_2 C8_2 1.377(3) . ?
C7_2 C12_2 1.383(3) . ?
C8_2 C9_2 1.381(3) . ?
C8_2 H8_2 0.9300 . ?
C9_2 C10_2 1.366(4) . ?
C9_2 H9_2 0.9300 . ?
C10_2 C11_2 1.362(4) . ?
C10_2 H10_2 0.9300 . ?
C11_2 C12_2 1.371(3) . ?
C11_2 H11_2 0.9300 . ?
C12_2 H12_2 0.9300 . ?
C13_2 C18_2 1.385(2) . ?
C13_2 C14_2 1.392(2) . ?
C13_2 C4_2 1.484(2) . ?
C14_2 C15_2 1.371(3) . ?
C14_2 H14_2 0.9300 . ?
C15_2 C16_2 1.382(3) . ?
C15_2 H15_2 0.9300 . ?
C16_2 C17_2 1.384(3) . ?
C17_2 C18_2 1.376(3) . ?
C17_2 H17_2 0.9300 . ?
C18_2 H18_2 0.9300 . ?
C19_2 H19A_2 0.9600 . ?
C19_2 H19B_2 0.9600 . ?
C19_2 H19C_2 0.9600 . ?
C20_2 C21_2 1.478(3) . ?
C21_2 C26_2 1.382(3) . ?
C21_2 C22_2 1.395(3) . ?
C22_2 C23_2 1.372(3) . ?
C22_2 H22_2 0.9300 . ?
C23_2 C24_2 1.380(3) . ?
C23_2 H23_2 0.9300 . ?
C24_2 C25_2 1.384(3) . ?
C25_2 C26_2 1.376(3) . ?
C25_2 H25_2 0.9300 . ?
C26_2 H26_2 0.9300 . ?
C27_2 H27A_2 0.9600 . ?
C27_2 H27B_2 0.9600 . ?
C27_2 H27C_2 0.9600 . ?
S1_3 C2_3 1.7221(17) . ?
S1_3 C5_3 1.7453(18) . ?
O2_3 C16_3 1.365(2) . ?
O2_3 C19_3 1.427(3) . ?
C2_3 N1_3 1.327(2) . ?
C2_3 C3_3 1.414(2) . ?
O3_3 C20_3 1.236(2) . ?
C3_3 C4_3 1.432(2) . ?
C3_3 C6_3 1.455(2) . ?
O4_3 C24_3 1.366(2) . ?
O4_3 C27_3 1.423(3) . ?
C5_3 C4_3 1.385(2) . ?
C5_3 C20_3 1.456(2) . ?
C6_3 O1_3 1.234(2) . ?
C6_3 C7_3 1.488(2) . ?
C7_3 C8_3 1.375(3) . ?
C7_3 C12_3 1.383(2) . ?
C8_3 C9_3 1.371(3) . ?
C8_3 H8_3 0.9300 . ?
C9_3 C10_3 1.368(3) . ?
C9_3 H9_3 0.9300 . ?
C10_3 C11_3 1.369(3) . ?
C10_3 H10_3 0.9300 . ?
C11_3 C12_3 1.370(3) . ?
C11_3 H11_3 0.9300 . ?
C12_3 H12_3 0.9300 . ?
C13_3 C18_3 1.382(2) . ?
C13_3 C14_3 1.393(2) . ?
C13_3 C4_3 1.483(2) . ?
C14_3 C15_3 1.367(2) . ?
C14_3 H14_3 0.9300 . ?
C15_3 C16_3 1.385(3) . ?
C15_3 H15_3 0.9300 . ?
C16_3 C17_3 1.382(3) . ?
C17_3 C18_3 1.378(3) . ?
C17_3 H17_3 0.9300 . ?
C18_3 H18_3 0.9300 . ?
C19_3 H19A_3 0.9600 . ?
C19_3 H19B_3 0.9600 . ?
C19_3 H19C_3 0.9600 . ?
C20_3 C21_3 1.478(3) . ?
C21_3 C26_3 1.382(3) . ?
C21_3 C22_3 1.390(3) . ?
C22_3 C23_3 1.372(3) . ?
C22_3 H22_3 0.9300 . ?
C23_3 C24_3 1.384(3) . ?
C23_3 H23_3 0.9300 . ?
C24_3 C25_3 1.377(3) . ?
C25_3 C26_3 1.380(3) . ?
C25_3 H25_3 0.9300 . ?
C26_3 H26_3 0.9300 . ?
C27_3 H27A_3 0.9600 . ?
C27_3 H27B_3 0.9600 . ?
C27_3 H27C_3 0.9600 . ?
N1_3 H1N1_3 0.876(14) . ?
N1_3 H1N2_3 0.881(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2_1 S1_1 C5_1 91.79(8) . . ?
C2_1 N1_1 H1N1_1 117.8(14) . . ?
C2_1 N1_1 H1N2_1 120.5(13) . . ?
H1N1_1 N1_1 H1N2_1 119.6(19) . . ?
N1_1 C2_1 C3_1 128.48(15) . . ?
N1_1 C2_1 S1_1 119.89(13) . . ?
C3_1 C2_1 S1_1 111.61(12) . . ?
C16_1 O2_1 C19_1 117.33(17) . . ?
C2_1 C3_1 C4_1 111.99(14) . . ?
C2_1 C3_1 C6_1 119.28(15) . . ?
C4_1 C3_1 C6_1 128.69(14) . . ?
C5_1 C4_1 C3_1 112.88(14) . . ?
C5_1 C4_1 C13_1 123.70(15) . . ?
C3_1 C4_1 C13_1 123.35(14) . . ?
C24_1 O4_1 C27_1 118.72(16) . . ?
C4_1 C5_1 C20_1 135.32(16) . . ?
C4_1 C5_1 S1_1 111.51(12) . . ?
C20_1 C5_1 S1_1 113.17(12) . . ?
O1_1 C6_1 C3_1 119.99(15) . . ?
O1_1 C6_1 C7_1 117.84(15) . . ?
C3_1 C6_1 C7_1 122.11(14) . . ?
C8_1 C7_1 C12_1 119.04(17) . . ?
C8_1 C7_1 C6_1 118.81(16) . . ?
C12_1 C7_1 C6_1 122.03(16) . . ?
C9_1 C8_1 C7_1 120.31(19) . . ?
C9_1 C8_1 H8_1 119.8 . . ?
C7_1 C8_1 H8_1 119.8 . . ?
C10_1 C9_1 C8_1 119.9(2) . . ?
C10_1 C9_1 H9_1 120.0 . . ?
C8_1 C9_1 H9_1 120.0 . . ?
C11_1 C10_1 C9_1 120.1(2) . . ?
C11_1 C10_1 H10_1 119.9 . . ?
C9_1 C10_1 H10_1 119.9 . . ?
C10_1 C11_1 C12_1 120.5(2) . . ?
C10_1 C11_1 H11_1 119.7 . . ?
C12_1 C11_1 H11_1 119.7 . . ?
C11_1 C12_1 C7_1 120.04(19) . . ?
C11_1 C12_1 H12_1 120.0 . . ?
C7_1 C12_1 H12_1 120.0 . . ?
C14_1 C13_1 C18_1 117.88(15) . . ?
C14_1 C13_1 C4_1 120.14(15) . . ?
C18_1 C13_1 C4_1 121.94(15) . . ?
C13_1 C14_1 C15_1 122.10(16) . . ?
C13_1 C14_1 H14_1 119.0 . . ?
C15_1 C14_1 H14_1 119.0 . . ?
C16_1 C15_1 C14_1 119.16(17) . . ?
C16_1 C15_1 H15_1 120.4 . . ?
C14_1 C15_1 H15_1 120.4 . . ?
O2_1 C16_1 C15_1 123.88(18) . . ?
O2_1 C16_1 C17_1 116.32(16) . . ?
C15_1 C16_1 C17_1 119.80(17) . . ?
C18_1 C17_1 C16_1 120.26(17) . . ?
C18_1 C17_1 H17_1 119.9 . . ?
C16_1 C17_1 H17_1 119.9 . . ?
C17_1 C18_1 C13_1 120.66(16) . . ?
C17_1 C18_1 H18_1 119.7 . . ?
C13_1 C18_1 H18_1 119.7 . . ?
O2_1 C19_1 H19A_1 109.5 . . ?
O2_1 C19_1 H19B_1 109.5 . . ?
H19A_1 C19_1 H19B_1 109.5 . . ?
O2_1 C19_1 H19C_1 109.5 . . ?
H19A_1 C19_1 H19C_1 109.5 . . ?
H19B_1 C19_1 H19C_1 109.5 . . ?
O3_1 C20_1 C5_1 118.37(17) . . ?
O3_1 C20_1 C21_1 119.35(15) . . ?
C5_1 C20_1 C21_1 122.22(15) . . ?
C26_1 C21_1 C22_1 117.76(17) . . ?
C26_1 C21_1 C20_1 119.72(17) . . ?
C22_1 C21_1 C20_1 122.44(16) . . ?
C23_1 C22_1 C21_1 121.54(17) . . ?
C23_1 C22_1 H22_1 119.2 . . ?
C21_1 C22_1 H22_1 119.2 . . ?
C22_1 C23_1 C24_1 119.81(18) . . ?
C22_1 C23_1 H23_1 120.1 . . ?
C24_1 C23_1 H23_1 120.1 . . ?
O4_1 C24_1 C25_1 124.23(17) . . ?
O4_1 C24_1 C23_1 115.65(17) . . ?
C25_1 C24_1 C23_1 120.09(18) . . ?
C24_1 C25_1 C26_1 119.55(17) . . ?
C24_1 C25_1 H25_1 120.2 . . ?
C26_1 C25_1 H25_1 120.2 . . ?
C25_1 C26_1 C21_1 121.25(18) . . ?
C25_1 C26_1 H26_1 119.4 . . ?
C21_1 C26_1 H26_1 119.4 . . ?
O4_1 C27_1 H27A_1 109.5 . . ?
O4_1 C27_1 H27B_1 109.5 . . ?
H27A_1 C27_1 H27B_1 109.5 . . ?
O4_1 C27_1 H27C_1 109.5 . . ?
H27A_1 C27_1 H27C_1 109.5 . . ?
H27B_1 C27_1 H27C_1 109.5 . . ?
C2_2 S1_2 C5_2 91.47(8) . . ?
C2_2 N1_2 H1N1_2 120.2(16) . . ?
C2_2 N1_2 H1N2_2 117.6(14) . . ?
H1N1_2 N1_2 H1N2_2 122(2) . . ?
C16_2 O2_2 C19_2 117.01(18) . . ?
N1_2 C2_2 C3_2 128.37(16) . . ?
N1_2 C2_2 S1_2 119.54(14) . . ?
C3_2 C2_2 S1_2 112.03(13) . . ?
C2_2 C3_2 C4_2 111.76(15) . . ?
C2_2 C3_2 C6_2 119.67(16) . . ?
C4_2 C3_2 C6_2 128.56(16) . . ?
C24_2 O4_2 C27_2 117.9(2) . . ?
C4_2 C5_2 C20_2 134.40(17) . . ?
C4_2 C5_2 S1_2 112.00(13) . . ?
C20_2 C5_2 S1_2 113.59(12) . . ?
O1_2 C6_2 C3_2 119.11(17) . . ?
O1_2 C6_2 C7_2 118.29(16) . . ?
C3_2 C6_2 C7_2 122.60(17) . . ?
C8_2 C7_2 C12_2 119.06(18) . . ?
C8_2 C7_2 C6_2 123.17(17) . . ?
C12_2 C7_2 C6_2 117.71(19) . . ?
C7_2 C8_2 C9_2 120.1(2) . . ?
C7_2 C8_2 H8_2 120.0 . . ?
C9_2 C8_2 H8_2 120.0 . . ?
C10_2 C9_2 C8_2 119.9(3) . . ?
C10_2 C9_2 H9_2 120.1 . . ?
C8_2 C9_2 H9_2 120.1 . . ?
C11_2 C10_2 C9_2 120.6(2) . . ?
C11_2 C10_2 H10_2 119.7 . . ?
C9_2 C10_2 H10_2 119.7 . . ?
C10_2 C11_2 C12_2 119.9(2) . . ?
C10_2 C11_2 H11_2 120.0 . . ?
C12_2 C11_2 H11_2 120.0 . . ?
C11_2 C12_2 C7_2 120.5(2) . . ?
C11_2 C12_2 H12_2 119.8 . . ?
C7_2 C12_2 H12_2 119.8 . . ?
C18_2 C13_2 C14_2 117.83(16) . . ?
C18_2 C13_2 C4_2 120.17(15) . . ?
C14_2 C13_2 C4_2 122.00(16) . . ?
C15_2 C14_2 C13_2 120.81(17) . . ?
C15_2 C14_2 H14_2 119.6 . . ?
C13_2 C14_2 H14_2 119.6 . . ?
C14_2 C15_2 C16_2 120.48(17) . . ?
C14_2 C15_2 H15_2 119.8 . . ?
C16_2 C15_2 H15_2 119.8 . . ?
O2_2 C16_2 C15_2 116.03(17) . . ?
O2_2 C16_2 C17_2 124.25(18) . . ?
C15_2 C16_2 C17_2 119.73(17) . . ?
C18_2 C17_2 C16_2 119.19(18) . . ?
C18_2 C17_2 H17_2 120.4 . . ?
C16_2 C17_2 H17_2 120.4 . . ?
C17_2 C18_2 C13_2 121.96(17) . . ?
C17_2 C18_2 H18_2 119.0 . . ?
C13_2 C18_2 H18_2 119.0 . . ?
O2_2 C19_2 H19A_2 109.5 . . ?
O2_2 C19_2 H19B_2 109.5 . . ?
H19A_2 C19_2 H19B_2 109.5 . . ?
O2_2 C19_2 H19C_2 109.5 . . ?
H19A_2 C19_2 H19C_2 109.5 . . ?
H19B_2 C19_2 H19C_2 109.5 . . ?
O3_2 C20_2 C5_2 117.85(17) . . ?
O3_2 C20_2 C21_2 120.24(16) . . ?
C5_2 C20_2 C21_2 121.89(15) . . ?
C26_2 C21_2 C22_2 118.45(18) . . ?
C26_2 C21_2 C20_2 118.51(17) . . ?
C22_2 C21_2 C20_2 123.00(17) . . ?
C23_2 C22_2 C21_2 120.50(18) . . ?
C23_2 C22_2 H22_2 119.7 . . ?
C21_2 C22_2 H22_2 119.7 . . ?
C22_2 C23_2 C24_2 120.11(19) . . ?
C22_2 C23_2 H23_2 119.9 . . ?
C24_2 C23_2 H23_2 119.9 . . ?
O4_2 C24_2 C23_2 115.5(2) . . ?
O4_2 C24_2 C25_2 124.3(2) . . ?
C23_2 C24_2 C25_2 120.2(2) . . ?
C26_2 C25_2 C24_2 119.2(2) . . ?
C26_2 C25_2 H25_2 120.4 . . ?
C24_2 C25_2 H25_2 120.4 . . ?
C25_2 C26_2 C21_2 121.41(19) . . ?
C25_2 C26_2 H26_2 119.3 . . ?
C21_2 C26_2 H26_2 119.3 . . ?
O4_2 C27_2 H27A_2 109.5 . . ?
O4_2 C27_2 H27B_2 109.5 . . ?
H27A_2 C27_2 H27B_2 109.5 . . ?
O4_2 C27_2 H27C_2 109.5 . . ?
H27A_2 C27_2 H27C_2 109.5 . . ?
H27B_2 C27_2 H27C_2 109.5 . . ?
C5_2 C4_2 C3_2 112.55(15) . . ?
C5_2 C4_2 C13_2 123.86(16) . . ?
C3_2 C4_2 C13_2 123.57(14) . . ?
C2_3 S1_3 C5_3 91.58(8) . . ?
C16_3 O2_3 C19_3 118.56(17) . . ?
N1_3 C2_3 C3_3 128.26(16) . . ?
N1_3 C2_3 S1_3 119.78(13) . . ?
C3_3 C2_3 S1_3 111.93(13) . . ?
C2_3 C3_3 C4_3 111.86(14) . . ?
C2_3 C3_3 C6_3 119.06(15) . . ?
C4_3 C3_3 C6_3 129.05(15) . . ?
C24_3 O4_3 C27_3 118.26(17) . . ?
C4_3 C5_3 C20_3 134.93(17) . . ?
C4_3 C5_3 S1_3 112.16(13) . . ?
C20_3 C5_3 S1_3 112.90(12) . . ?
O1_3 C6_3 C3_3 119.37(16) . . ?
O1_3 C6_3 C7_3 117.18(15) . . ?
C3_3 C6_3 C7_3 123.44(15) . . ?
C8_3 C7_3 C12_3 119.09(16) . . ?
C8_3 C7_3 C6_3 122.86(15) . . ?
C12_3 C7_3 C6_3 117.90(16) . . ?
C9_3 C8_3 C7_3 119.96(18) . . ?
C9_3 C8_3 H8_3 120.0 . . ?
C7_3 C8_3 H8_3 120.0 . . ?
C10_3 C9_3 C8_3 120.4(2) . . ?
C10_3 C9_3 H9_3 119.8 . . ?
C8_3 C9_3 H9_3 119.8 . . ?
C9_3 C10_3 C11_3 120.3(2) . . ?
C9_3 C10_3 H10_3 119.9 . . ?
C11_3 C10_3 H10_3 119.9 . . ?
C10_3 C11_3 C12_3 119.45(19) . . ?
C10_3 C11_3 H11_3 120.3 . . ?
C12_3 C11_3 H11_3 120.3 . . ?
C11_3 C12_3 C7_3 120.76(18) . . ?
C11_3 C12_3 H12_3 119.6 . . ?
C7_3 C12_3 H12_3 119.6 . . ?
C18_3 C13_3 C14_3 117.70(16) . . ?
C18_3 C13_3 C4_3 121.00(15) . . ?
C14_3 C13_3 C4_3 121.29(15) . . ?
C15_3 C14_3 C13_3 120.79(16) . . ?
C15_3 C14_3 H14_3 119.6 . . ?
C13_3 C14_3 H14_3 119.6 . . ?
C14_3 C15_3 C16_3 120.69(16) . . ?
C14_3 C15_3 H15_3 119.7 . . ?
C16_3 C15_3 H15_3 119.7 . . ?
O2_3 C16_3 C17_3 124.38(17) . . ?
O2_3 C16_3 C15_3 116.19(16) . . ?
C17_3 C16_3 C15_3 119.43(17) . . ?
C18_3 C17_3 C16_3 119.25(17) . . ?
C18_3 C17_3 H17_3 120.4 . . ?
C16_3 C17_3 H17_3 120.4 . . ?
C17_3 C18_3 C13_3 122.07(16) . . ?
C17_3 C18_3 H18_3 119.0 . . ?
C13_3 C18_3 H18_3 119.0 . . ?
O2_3 C19_3 H19A_3 109.5 . . ?
O2_3 C19_3 H19B_3 109.5 . . ?
H19A_3 C19_3 H19B_3 109.5 . . ?
O2_3 C19_3 H19C_3 109.5 . . ?
H19A_3 C19_3 H19C_3 109.5 . . ?
H19B_3 C19_3 H19C_3 109.5 . . ?
O3_3 C20_3 C5_3 117.59(17) . . ?
O3_3 C20_3 C21_3 118.92(16) . . ?
C5_3 C20_3 C21_3 123.49(15) . . ?
C26_3 C21_3 C22_3 118.17(18) . . ?
C26_3 C21_3 C20_3 123.33(17) . . ?
C22_3 C21_3 C20_3 118.34(17) . . ?
C23_3 C22_3 C21_3 120.94(18) . . ?
C23_3 C22_3 H22_3 119.5 . . ?
C21_3 C22_3 H22_3 119.5 . . ?
C22_3 C23_3 C24_3 119.96(19) . . ?
C22_3 C23_3 H23_3 120.0 . . ?
C24_3 C23_3 H23_3 120.0 . . ?
O4_3 C24_3 C25_3 124.99(18) . . ?
O4_3 C24_3 C23_3 115.06(18) . . ?
C25_3 C24_3 C23_3 119.95(19) . . ?
C24_3 C25_3 C26_3 119.56(18) . . ?
C24_3 C25_3 H25_3 120.2 . . ?
C26_3 C25_3 H25_3 120.2 . . ?
C25_3 C26_3 C21_3 121.33(17) . . ?
C25_3 C26_3 H26_3 119.3 . . ?
C21_3 C26_3 H26_3 119.3 . . ?
O4_3 C27_3 H27A_3 109.5 . . ?
O4_3 C27_3 H27B_3 109.5 . . ?
H27A_3 C27_3 H27B_3 109.5 . . ?
O4_3 C27_3 H27C_3 109.5 . . ?
H27A_3 C27_3 H27C_3 109.5 . . ?
H27B_3 C27_3 H27C_3 109.5 . . ?
C5_3 C4_3 C3_3 112.34(15) . . ?
C5_3 C4_3 C13_3 123.65(15) . . ?
C3_3 C4_3 C13_3 123.98(14) . . ?
C2_3 N1_3 H1N1_3 118.1(14) . . ?
C2_3 N1_3 H1N2_3 118.6(14) . . ?
H1N1_3 N1_3 H1N2_3 123(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
C5_1 S1_1 C2_1 N1_1 177.06(15) . . . . ?
C5_1 S1_1 C2_1 C3_1 -4.51(14) . . . . ?
N1_1 C2_1 C3_1 C4_1 -177.71(17) . . . . ?
S1_1 C2_1 C3_1 C4_1 4.02(19) . . . . ?
N1_1 C2_1 C3_1 C6_1 4.5(3) . . . . ?
S1_1 C2_1 C3_1 C6_1 -173.81(13) . . . . ?
C2_1 C3_1 C4_1 C5_1 -1.1(2) . . . . ?
C6_1 C3_1 C4_1 C5_1 176.50(17) . . . . ?
C2_1 C3_1 C4_1 C13_1 175.90(15) . . . . ?
C6_1 C3_1 C4_1 C13_1 -6.5(3) . . . . ?
C3_1 C4_1 C5_1 C20_1 176.6(2) . . . . ?
C13_1 C4_1 C5_1 C20_1 -0.4(3) . . . . ?
C3_1 C4_1 C5_1 S1_1 -2.31(19) . . . . ?
C13_1 C4_1 C5_1 S1_1 -179.27(13) . . . . ?
C2_1 S1_1 C5_1 C4_1 3.92(14) . . . . ?
C2_1 S1_1 C5_1 C20_1 -175.22(14) . . . . ?
C2_1 C3_1 C6_1 O1_1 -24.6(3) . . . . ?
C4_1 C3_1 C6_1 O1_1 157.96(18) . . . . ?
C2_1 C3_1 C6_1 C7_1 152.45(17) . . . . ?
C4_1 C3_1 C6_1 C7_1 -25.0(3) . . . . ?
O1_1 C6_1 C7_1 C8_1 -44.4(3) . . . . ?
C3_1 C6_1 C7_1 C8_1 138.45(19) . . . . ?
O1_1 C6_1 C7_1 C12_1 131.5(2) . . . . ?
C3_1 C6_1 C7_1 C12_1 -45.6(3) . . . . ?
C12_1 C7_1 C8_1 C9_1 2.9(3) . . . . ?
C6_1 C7_1 C8_1 C9_1 178.9(2) . . . . ?
C7_1 C8_1 C9_1 C10_1 -2.4(4) . . . . ?
C8_1 C9_1 C10_1 C11_1 0.0(4) . . . . ?
C9_1 C10_1 C11_1 C12_1 1.8(4) . . . . ?
C10_1 C11_1 C12_1 C7_1 -1.2(4) . . . . ?
C8_1 C7_1 C12_1 C11_1 -1.1(3) . . . . ?
C6_1 C7_1 C12_1 C11_1 -177.0(2) . . . . ?
C5_1 C4_1 C13_1 C14_1 118.2(2) . . . . ?
C3_1 C4_1 C13_1 C14_1 -58.5(2) . . . . ?
C5_1 C4_1 C13_1 C18_1 -59.6(2) . . . . ?
C3_1 C4_1 C13_1 C18_1 123.80(18) . . . . ?
C18_1 C13_1 C14_1 C15_1 3.2(3) . . . . ?
C4_1 C13_1 C14_1 C15_1 -174.60(17) . . . . ?
C13_1 C14_1 C15_1 C16_1 -1.3(3) . . . . ?
C19_1 O2_1 C16_1 C15_1 -8.6(3) . . . . ?
C19_1 O2_1 C16_1 C17_1 171.1(2) . . . . ?
C14_1 C15_1 C16_1 O2_1 177.35(19) . . . . ?
C14_1 C15_1 C16_1 C17_1 -2.4(3) . . . . ?
O2_1 C16_1 C17_1 C18_1 -175.78(18) . . . . ?
C15_1 C16_1 C17_1 C18_1 4.0(3) . . . . ?
C16_1 C17_1 C18_1 C13_1 -2.0(3) . . . . ?
C14_1 C13_1 C18_1 C17_1 -1.6(3) . . . . ?
C4_1 C13_1 C18_1 C17_1 176.19(16) . . . . ?
C4_1 C5_1 C20_1 O3_1 165.0(2) . . . . ?
S1_1 C5_1 C20_1 O3_1 -16.1(2) . . . . ?
C4_1 C5_1 C20_1 C21_1 -17.9(3) . . . . ?
S1_1 C5_1 C20_1 C21_1 160.97(14) . . . . ?
O3_1 C20_1 C21_1 C26_1 -41.0(3) . . . . ?
C5_1 C20_1 C21_1 C26_1 141.88(18) . . . . ?
O3_1 C20_1 C21_1 C22_1 135.53(19) . . . . ?
C5_1 C20_1 C21_1 C22_1 -41.5(3) . . . . ?
C26_1 C21_1 C22_1 C23_1 -1.0(3) . . . . ?
C20_1 C21_1 C22_1 C23_1 -177.60(16) . . . . ?
C21_1 C22_1 C23_1 C24_1 0.8(3) . . . . ?
C27_1 O4_1 C24_1 C25_1 22.1(3) . . . . ?
C27_1 O4_1 C24_1 C23_1 -159.70(18) . . . . ?
C22_1 C23_1 C24_1 O4_1 -178.70(17) . . . . ?
C22_1 C23_1 C24_1 C25_1 -0.4(3) . . . . ?
O4_1 C24_1 C25_1 C26_1 178.47(18) . . . . ?
C23_1 C24_1 C25_1 C26_1 0.4(3) . . . . ?
C24_1 C25_1 C26_1 C21_1 -0.6(3) . . . . ?
C22_1 C21_1 C26_1 C25_1 0.9(3) . . . . ?
C20_1 C21_1 C26_1 C25_1 177.62(17) . . . . ?
C5_2 S1_2 C2_2 N1_2 178.72(16) . . . . ?
C5_2 S1_2 C2_2 C3_2 -3.93(14) . . . . ?
N1_2 C2_2 C3_2 C4_2 -179.98(18) . . . . ?
S1_2 C2_2 C3_2 C4_2 2.97(19) . . . . ?
N1_2 C2_2 C3_2 C6_2 -0.5(3) . . . . ?
S1_2 C2_2 C3_2 C6_2 -177.51(13) . . . . ?
C2_2 S1_2 C5_2 C4_2 3.98(14) . . . . ?
C2_2 S1_2 C5_2 C20_2 -175.81(13) . . . . ?
C2_2 C3_2 C6_2 O1_2 -29.1(3) . . . . ?
C4_2 C3_2 C6_2 O1_2 150.29(19) . . . . ?
C2_2 C3_2 C6_2 C7_2 149.75(17) . . . . ?
C4_2 C3_2 C6_2 C7_2 -30.8(3) . . . . ?
O1_2 C6_2 C7_2 C8_2 142.1(2) . . . . ?
C3_2 C6_2 C7_2 C8_2 -36.8(3) . . . . ?
O1_2 C6_2 C7_2 C12_2 -35.1(3) . . . . ?
C3_2 C6_2 C7_2 C12_2 146.04(19) . . . . ?
C12_2 C7_2 C8_2 C9_2 -0.6(3) . . . . ?
C6_2 C7_2 C8_2 C9_2 -177.8(2) . . . . ?
C7_2 C8_2 C9_2 C10_2 -0.5(4) . . . . ?
C8_2 C9_2 C10_2 C11_2 0.7(4) . . . . ?
C9_2 C10_2 C11_2 C12_2 0.3(4) . . . . ?
C10_2 C11_2 C12_2 C7_2 -1.5(4) . . . . ?
C8_2 C7_2 C12_2 C11_2 1.6(3) . . . . ?
C6_2 C7_2 C12_2 C11_2 178.9(2) . . . . ?
C18_2 C13_2 C14_2 C15_2 0.3(2) . . . . ?
C4_2 C13_2 C14_2 C15_2 179.96(16) . . . . ?
C13_2 C14_2 C15_2 C16_2 -0.2(3) . . . . ?
C19_2 O2_2 C16_2 C15_2 -177.7(2) . . . . ?
C19_2 O2_2 C16_2 C17_2 2.2(3) . . . . ?
C14_2 C15_2 C16_2 O2_2 -179.95(18) . . . . ?
C14_2 C15_2 C16_2 C17_2 0.1(3) . . . . ?
O2_2 C16_2 C17_2 C18_2 179.85(18) . . . . ?
C15_2 C16_2 C17_2 C18_2 -0.2(3) . . . . ?
C16_2 C17_2 C18_2 C13_2 0.4(3) . . . . ?
C14_2 C13_2 C18_2 C17_2 -0.4(2) . . . . ?
C4_2 C13_2 C18_2 C17_2 179.92(16) . . . . ?
C4_2 C5_2 C20_2 O3_2 166.87(19) . . . . ?
S1_2 C5_2 C20_2 O3_2 -13.4(2) . . . . ?
C4_2 C5_2 C20_2 C21_2 -11.7(3) . . . . ?
S1_2 C5_2 C20_2 C21_2 167.99(13) . . . . ?
O3_2 C20_2 C21_2 C26_2 -47.1(2) . . . . ?
C5_2 C20_2 C21_2 C26_2 131.48(18) . . . . ?
O3_2 C20_2 C21_2 C22_2 135.10(18) . . . . ?
C5_2 C20_2 C21_2 C22_2 -46.3(2) . . . . ?
C26_2 C21_2 C22_2 C23_2 -2.3(3) . . . . ?
C20_2 C21_2 C22_2 C23_2 175.52(16) . . . . ?
C21_2 C22_2 C23_2 C24_2 -0.4(3) . . . . ?
C27_2 O4_2 C24_2 C23_2 170.3(2) . . . . ?
C27_2 O4_2 C24_2 C25_2 -9.2(3) . . . . ?
C22_2 C23_2 C24_2 O4_2 -177.24(18) . . . . ?
C22_2 C23_2 C24_2 C25_2 2.2(3) . . . . ?
O4_2 C24_2 C25_2 C26_2 178.1(2) . . . . ?
C23_2 C24_2 C25_2 C26_2 -1.4(3) . . . . ?
C24_2 C25_2 C26_2 C21_2 -1.4(3) . . . . ?
C22_2 C21_2 C26_2 C25_2 3.2(3) . . . . ?
C20_2 C21_2 C26_2 C25_2 -174.73(18) . . . . ?
C20_2 C5_2 C4_2 C3_2 176.74(18) . . . . ?
S1_2 C5_2 C4_2 C3_2 -2.99(19) . . . . ?
C20_2 C5_2 C4_2 C13_2 -4.3(3) . . . . ?
S1_2 C5_2 C4_2 C13_2 175.98(13) . . . . ?
C2_2 C3_2 C4_2 C5_2 0.0(2) . . . . ?
C6_2 C3_2 C4_2 C5_2 -179.43(17) . . . . ?
C2_2 C3_2 C4_2 C13_2 -178.93(15) . . . . ?
C6_2 C3_2 C4_2 C13_2 1.6(3) . . . . ?
C18_2 C13_2 C4_2 C5_2 -54.8(2) . . . . ?
C14_2 C13_2 C4_2 C5_2 125.53(19) . . . . ?
C18_2 C13_2 C4_2 C3_2 124.01(18) . . . . ?
C14_2 C13_2 C4_2 C3_2 -55.6(2) . . . . ?
C5_3 S1_3 C2_3 N1_3 178.46(16) . . . . ?
C5_3 S1_3 C2_3 C3_3 -3.28(14) . . . . ?
N1_3 C2_3 C3_3 C4_3 -178.94(18) . . . . ?
S1_3 C2_3 C3_3 C4_3 2.98(19) . . . . ?
N1_3 C2_3 C3_3 C6_3 2.9(3) . . . . ?
S1_3 C2_3 C3_3 C6_3 -175.13(13) . . . . ?
C2_3 S1_3 C5_3 C4_3 2.80(15) . . . . ?
C2_3 S1_3 C5_3 C20_3 -176.50(14) . . . . ?
C2_3 C3_3 C6_3 O1_3 -21.4(3) . . . . ?
C4_3 C3_3 C6_3 O1_3 160.87(18) . . . . ?
C2_3 C3_3 C6_3 C7_3 157.56(16) . . . . ?
C4_3 C3_3 C6_3 C7_3 -20.2(3) . . . . ?
O1_3 C6_3 C7_3 C8_3 129.6(2) . . . . ?
C3_3 C6_3 C7_3 C8_3 -49.4(3) . . . . ?
O1_3 C6_3 C7_3 C12_3 -45.9(2) . . . . ?
C3_3 C6_3 C7_3 C12_3 135.10(19) . . . . ?
C12_3 C7_3 C8_3 C9_3 0.7(3) . . . . ?
C6_3 C7_3 C8_3 C9_3 -174.7(2) . . . . ?
C7_3 C8_3 C9_3 C10_3 -2.8(4) . . . . ?
C8_3 C9_3 C10_3 C11_3 2.1(5) . . . . ?
C9_3 C10_3 C11_3 C12_3 0.7(5) . . . . ?
C10_3 C11_3 C12_3 C7_3 -2.8(4) . . . . ?
C8_3 C7_3 C12_3 C11_3 2.1(3) . . . . ?
C6_3 C7_3 C12_3 C11_3 177.8(2) . . . . ?
C18_3 C13_3 C14_3 C15_3 -1.7(3) . . . . ?
C4_3 C13_3 C14_3 C15_3 177.98(16) . . . . ?
C13_3 C14_3 C15_3 C16_3 -0.6(3) . . . . ?
C19_3 O2_3 C16_3 C17_3 -3.6(3) . . . . ?
C19_3 O2_3 C16_3 C15_3 177.0(2) . . . . ?
C14_3 C15_3 C16_3 O2_3 -178.51(17) . . . . ?
C14_3 C15_3 C16_3 C17_3 2.1(3) . . . . ?
O2_3 C16_3 C17_3 C18_3 179.35(18) . . . . ?
C15_3 C16_3 C17_3 C18_3 -1.3(3) . . . . ?
C16_3 C17_3 C18_3 C13_3 -1.0(3) . . . . ?
C14_3 C13_3 C18_3 C17_3 2.5(3) . . . . ?
C4_3 C13_3 C18_3 C17_3 -177.17(16) . . . . ?
C4_3 C5_3 C20_3 O3_3 169.9(2) . . . . ?
S1_3 C5_3 C20_3 O3_3 -11.0(2) . . . . ?
C4_3 C5_3 C20_3 C21_3 -10.5(3) . . . . ?
S1_3 C5_3 C20_3 C21_3 168.54(14) . . . . ?
O3_3 C20_3 C21_3 C26_3 127.1(2) . . . . ?
C5_3 C20_3 C21_3 C26_3 -52.4(3) . . . . ?
O3_3 C20_3 C21_3 C22_3 -48.2(3) . . . . ?
C5_3 C20_3 C21_3 C22_3 132.24(19) . . . . ?
C26_3 C21_3 C22_3 C23_3 2.8(3) . . . . ?
C20_3 C21_3 C22_3 C23_3 178.35(18) . . . . ?
C21_3 C22_3 C23_3 C24_3 -2.0(3) . . . . ?
C27_3 O4_3 C24_3 C25_3 0.4(3) . . . . ?
C27_3 O4_3 C24_3 C23_3 179.9(2) . . . . ?
C22_3 C23_3 C24_3 O4_3 179.83(19) . . . . ?
C22_3 C23_3 C24_3 C25_3 -0.6(3) . . . . ?
O4_3 C24_3 C25_3 C26_3 -178.12(18) . . . . ?
C23_3 C24_3 C25_3 C26_3 2.4(3) . . . . ?
C24_3 C25_3 C26_3 C21_3 -1.6(3) . . . . ?
C22_3 C21_3 C26_3 C25_3 -1.0(3) . . . . ?
C20_3 C21_3 C26_3 C25_3 -176.31(17) . . . . ?
C20_3 C5_3 C4_3 C3_3 177.51(19) . . . . ?
S1_3 C5_3 C4_3 C3_3 -1.6(2) . . . . ?
C20_3 C5_3 C4_3 C13_3 -0.7(3) . . . . ?
S1_3 C5_3 C4_3 C13_3 -179.74(13) . . . . ?
C2_3 C3_3 C4_3 C5_3 -0.9(2) . . . . ?
C6_3 C3_3 C4_3 C5_3 177.00(17) . . . . ?
C2_3 C3_3 C4_3 C13_3 177.27(15) . . . . ?
C6_3 C3_3 C4_3 C13_3 -4.9(3) . . . . ?
C18_3 C13_3 C4_3 C5_3 121.26(19) . . . . ?
C14_3 C13_3 C4_3 C5_3 -58.4(2) . . . . ?
C18_3 C13_3 C4_3 C3_3 -56.7(2) . . . . ?
C14_3 C13_3 C4_3 C3_3 123.69(18) . . . . ?

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
N1_1 H1N1_1 O1_1 0.870(14) 2.131(19) 2.734(2) 126.0(17) . yes
N1_1 H1N1_1 O1_1 0.870(14) 2.249(17) 3.009(2) 145.9(18) 3_576 yes
N1_1 H1N2_1 O3_2 0.884(14) 1.996(14) 2.867(2) 168.1(18) 3_676 yes
N1_2 H1N1_2 O1_2 0.880(15) 2.21(2) 2.782(2) 122.4(19) . yes
N1_2 H1N1_2 O1_3 0.880(15) 2.179(16) 3.014(2) 158(2) 1_545 yes
N1_2 H1N2_2 O3_1 0.870(14) 2.234(15) 3.070(2) 160.8(18) 3_666 yes
N1_3 H1N1_3 O3_3 0.876(14) 2.037(15) 2.900(2) 168.1(19) 2_655 yes
N1_3 H1N2_3 O1_2 0.881(14) 2.242(16) 3.057(2) 153.9(18) 1_565 yes
N1_3 H1N2_3 O1_3 0.881(14) 2.079(18) 2.692(2) 125.9(17) . yes

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.038




_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_NTTXXX
_database_code_depnum_ccdc_archive 'CCDC 2165911'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H17 N O3 S'
_chemical_formula_sum            'C20 H17 N O3 S'
_chemical_formula_weight         351.40

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   8.3532(10)
_cell_length_b                   19.2461(14)
_cell_length_c                   22.742(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3656.1(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4439
_cell_measurement_theta_min      3.3990
_cell_measurement_theta_max      26.1990

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.051
_exptl_crystal_size_min          0.049
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             1472.000
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0240
0 1 0 0.0266
5 0 1 0.1434
0 0 1 0.0010
0 0 -1 0.0479
-11 5 -6 0.1033
-6 -23 0 0.0604
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_min  0.735
_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 (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            31779
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.773
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25.025
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3215
_reflns_number_gt                2054
_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    'SHELXL-2018/3 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_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)+(0.0570P)²+0.8572P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3208
_refine_ls_number_parameters     280
_refine_ls_number_restraints     398
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.037
_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 0.34236(9) 0.69662(3) 0.47325(3) 0.0977(3) Uani 1 1 d . . . . .
C6 C 0.2859(14) 0.4959(7) 0.4417(5) 0.094(3) Uani 0.535(9) 1 d D U P A 1
O1 O 0.1418(14) 0.4784(9) 0.4550(5) 0.111(3) Uani 0.535(9) 1 d D U P A 1
O2 O 0.3750(10) 0.4525(2) 0.4114(4) 0.118(2) Uani 0.535(9) 1 d D U P A 1
C7 C 0.3227(13) 0.3811(4) 0.4079(4) 0.122(3) Uani 0.535(9) 1 d D U P A 1
H7A H 0.234190 0.373952 0.434900 0.146 Uiso 0.535(9) 1 calc R U P A 1
H7AB H 0.409533 0.350754 0.419767 0.146 Uiso 0.535(9) 1 calc R U P A 1
C7A C 0.2721(16) 0.3632(5) 0.3485(4) 0.179(4) Uani 0.535(9) 1 d D U P A 1
H7AA H 0.250419 0.314320 0.346370 0.268 Uiso 0.535(9) 1 calc R U P A 1
H7AC H 0.355564 0.374901 0.321234 0.268 Uiso 0.535(9) 1 calc R U P A 1
H7AD H 0.176881 0.388721 0.338773 0.268 Uiso 0.535(9) 1 calc R U P A 1
C6B C 0.2528(18) 0.5009(8) 0.4292(6) 0.091(3) Uani 0.465(9) 1 d D U P A 2
O1B O 0.1762(18) 0.4763(9) 0.4738(5) 0.102(3) Uani 0.465(9) 1 d D U P A 2
C7B C 0.2530(12) 0.3950(4) 0.3759(6) 0.122(3) Uani 0.465(9) 1 d D U P A 2
H7BA H 0.232762 0.385722 0.334684 0.146 Uiso 0.465(9) 1 calc R U P A 2
H7BB H 0.154739 0.387585 0.397753 0.146 Uiso 0.465(9) 1 calc R U P A 2
C7C C 0.3804(16) 0.3495(5) 0.3982(9) 0.215(6) Uani 0.465(9) 1 d D U P A 2
H7CA H 0.349490 0.301868 0.392980 0.323 Uiso 0.465(9) 1 calc R U P A 2
H7CB H 0.397437 0.358627 0.439179 0.323 Uiso 0.465(9) 1 calc R U P A 2
H7CC H 0.477463 0.358308 0.376827 0.323 Uiso 0.465(9) 1 calc R U P A 2
O2B O 0.3092(9) 0.4657(3) 0.3838(3) 0.0986(17) Uani 0.465(9) 1 d D U P A 2
C20 C 0.7784(5) 0.75071(18) 0.32205(16) 0.1238(10) Uani 1 1 d . . . . .
H20 H 0.705029 0.784204 0.310140 0.149 Uiso 1 1 calc R U . . .
C19 C 0.9199(6) 0.7431(2) 0.29150(19) 0.1494(13) Uani 1 1 d . . . . .
H19 H 0.941217 0.770650 0.258851 0.179 Uiso 1 1 calc R U . . .
C18 C 1.0264(5) 0.6955(3) 0.3093(2) 0.1485(14) Uani 1 1 d . . . . .
H18 H 1.121274 0.690020 0.288438 0.178 Uiso 1 1 calc R U . . .
C17 C 0.9990(4) 0.6548(2) 0.35748(18) 0.1328(12) Uani 1 1 d . . . . .
H17 H 1.076094 0.623024 0.369678 0.159 Uiso 1 1 calc R U . . .
C16 C 0.8541(4) 0.66091(16) 0.38867(14) 0.1112(9) Uani 1 1 d . . . . .
H16 H 0.833463 0.632791 0.421053 0.133 Uiso 1 1 calc R U . . .
C15 C 0.7438(3) 0.70911(14) 0.37040(13) 0.0956(7) Uani 1 1 d . . . . .
C14 C 0.5929(3) 0.72154(12) 0.40327(12) 0.0944(7) Uani 1 1 d . . . . .
C13 C 0.5620(3) 0.57087(13) 0.31036(11) 0.0925(7) Uani 1 1 d . . . . .
H13 H 0.491816 0.604313 0.296006 0.111 Uiso 1 1 calc R U . . .
C12 C 0.6590(4) 0.53376(18) 0.27164(13) 0.1176(10) Uani 1 1 d . . . . .
H12 H 0.654025 0.542804 0.231511 0.141 Uiso 1 1 calc R U . . .
C11 C 0.7609(4) 0.48431(18) 0.29238(17) 0.1239(10) Uani 1 1 d . . . . .
H11 H 0.825843 0.459710 0.266500 0.149 Uiso 1 1 calc R U . . .
C10 C 0.7674(4) 0.47109(17) 0.35066(17) 0.1325(11) Uani 1 1 d . . . . .
H10 H 0.836636 0.437208 0.364942 0.159 Uiso 1 1 calc R U . . .
C2 C 0.2570(4) 0.61627(12) 0.47700(11) 0.0902(7) Uani 1 1 d . . . . .
C3 C 0.3347(3) 0.56800(11) 0.44068(11) 0.0886(7) Uani 1 1 d . U . . .
O3 O 0.5537(2) 0.78262(9) 0.41320(10) 0.1236(7) Uani 1 1 d . . . . .
N1 N 0.1283(4) 0.60611(11) 0.51026(12) 0.1149(9) Uani 1 1 d D . . . .
H1N1 H 0.086(4) 0.5652(13) 0.5123(14) 0.138 Uiso 1 1 d D U . . .
H1N2 H 0.092(4) 0.6399(13) 0.5321(13) 0.138 Uiso 1 1 d D U . . .
C4 C 0.4674(3) 0.59748(11) 0.41084(10) 0.0810(6) Uani 1 1 d . . . . .
C5 C 0.4879(3) 0.66691(11) 0.42397(11) 0.0860(7) Uani 1 1 d . . . . .
C8 C 0.5699(3) 0.55832(11) 0.36874(10) 0.0808(6) Uani 1 1 d . . . . .
C9 C 0.6725(4) 0.50746(15) 0.38858(13) 0.1167(10) Uani 1 1 d . . . . .
H9 H 0.677192 0.497702 0.428596 0.140 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 C2 1.705(3) . ?
S1 C5 1.749(3) . ?
C6 O1 1.286(12) . ?
C6 O2 1.315(10) . ?
C6 C3 1.446(14) . ?
O2 C7 1.443(7) . ?
C7 C7A 1.457(8) . ?
C7 H7A 0.9700 . ?
C7 H7AB 0.9700 . ?
C7A H7AA 0.9600 . ?
C7A H7AC 0.9600 . ?
C7A H7AD 0.9600 . ?
C6B O1B 1.290(12) . ?
C6B O2B 1.321(10) . ?
C6B C3 1.485(17) . ?
C7B O2B 1.449(8) . ?
C7B C7C 1.468(9) . ?
C7B H7BA 0.9700 . ?
C7B H7BB 0.9700 . ?
C7C H7CA 0.9600 . ?
C7C H7CB 0.9600 . ?
C7C H7CC 0.9600 . ?
C20 C19 1.379(5) . ?
C20 C15 1.390(4) . ?
C20 H20 0.9300 . ?
C19 C18 1.340(5) . ?
C19 H19 0.9300 . ?
C18 C17 1.365(5) . ?
C18 H18 0.9300 . ?
C17 C16 1.408(4) . ?
C17 H17 0.9300 . ?
C16 C15 1.372(4) . ?
C16 H16 0.9300 . ?
C15 C14 1.485(4) . ?
C14 O3 1.241(3) . ?
C14 C5 1.448(4) . ?
C13 C8 1.351(3) . ?
C13 C12 1.393(4) . ?
C13 H13 0.9300 . ?
C12 C11 1.361(4) . ?
C12 H12 0.9300 . ?
C11 C10 1.351(4) . ?
C11 H11 0.9300 . ?
C10 C9 1.365(4) . ?
C10 H10 0.9300 . ?
C2 N1 1.329(4) . ?
C2 C3 1.402(3) . ?
C3 C4 1.418(3) . ?
N1 H1N1 0.87(2) . ?
N1 H1N2 0.87(2) . ?
C4 C5 1.380(3) . ?
C4 C8 1.489(3) . ?
C8 C9 1.377(3) . ?
C9 H9 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
C2 S1 C5 91.50(12) . . ?
O1 C6 O2 119.1(13) . . ?
O1 C6 C3 121.3(12) . . ?
O2 C6 C3 116.2(8) . . ?
C6 O2 C7 117.6(8) . . ?
O2 C7 C7A 111.3(9) . . ?
O2 C7 H7A 109.4 . . ?
C7A C7 H7A 109.4 . . ?
O2 C7 H7AB 109.4 . . ?
C7A C7 H7AB 109.4 . . ?
H7A C7 H7AB 108.0 . . ?
C7 C7A H7AA 109.5 . . ?
C7 C7A H7AC 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
C7 C7A H7AD 109.5 . . ?
H7AA C7A H7AD 109.5 . . ?
H7AC C7A H7AD 109.5 . . ?
O1B C6B O2B 127.1(16) . . ?
O1B C6B C3 114.2(12) . . ?
O2B C6B C3 114.8(10) . . ?
O2B C7B C7C 106.4(10) . . ?
O2B C7B H7BA 110.4 . . ?
C7C C7B H7BA 110.4 . . ?
O2B C7B H7BB 110.4 . . ?
C7C C7B H7BB 110.4 . . ?
H7BA C7B H7BB 108.6 . . ?
C7B C7C H7CA 109.5 . . ?
C7B C7C H7CB 109.5 . . ?
H7CA C7C H7CB 109.5 . . ?
C7B C7C H7CC 109.5 . . ?
H7CA C7C H7CC 109.5 . . ?
H7CB C7C H7CC 109.5 . . ?
C6B O2B C7B 117.5(10) . . ?
C19 C20 C15 121.0(4) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?
C18 C19 C20 119.3(4) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C19 C18 C17 121.6(4) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C17 C16 120.0(4) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C15 C16 C17 118.8(3) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C16 C15 C20 119.3(3) . . ?
C16 C15 C14 121.8(3) . . ?
C20 C15 C14 118.8(3) . . ?
O3 C14 C5 118.0(3) . . ?
O3 C14 C15 117.9(3) . . ?
C5 C14 C15 124.1(2) . . ?
C8 C13 C12 120.1(3) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
N1 C2 C3 127.8(2) . . ?
N1 C2 S1 120.01(18) . . ?
C3 C2 S1 112.2(2) . . ?
C2 C3 C4 112.2(2) . . ?
C2 C3 C6 119.7(4) . . ?
C4 C3 C6 127.8(4) . . ?
C2 C3 C6B 117.8(5) . . ?
C4 C3 C6B 128.6(5) . . ?
C2 N1 H1N1 120(2) . . ?
C2 N1 H1N2 119(2) . . ?
H1N1 N1 H1N2 120(3) . . ?
C5 C4 C3 112.4(2) . . ?
C5 C4 C8 123.9(2) . . ?
C3 C4 C8 123.68(19) . . ?
C4 C5 C14 135.1(2) . . ?
C4 C5 S1 111.6(2) . . ?
C14 C5 S1 113.08(17) . . ?
C13 C8 C9 118.6(2) . . ?
C13 C8 C4 120.9(2) . . ?
C9 C8 C4 120.5(2) . . ?
C10 C9 C8 121.3(3) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?

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
O1 C6 O2 C7 -16.0(15) . . . . ?
C3 C6 O2 C7 -175.4(10) . . . . ?
C6 O2 C7 C7A 111.6(11) . . . . ?
O1B C6B O2B C7B 14.0(19) . . . . ?
C3 C6B O2B C7B 170.1(9) . . . . ?
C7C C7B O2B C6B -101.2(14) . . . . ?
C15 C20 C19 C18 -1.0(6) . . . . ?
C20 C19 C18 C17 -0.7(6) . . . . ?
C19 C18 C17 C16 1.8(6) . . . . ?
C18 C17 C16 C15 -1.3(5) . . . . ?
C17 C16 C15 C20 -0.4(4) . . . . ?
C17 C16 C15 C14 -176.1(2) . . . . ?
C19 C20 C15 C16 1.5(4) . . . . ?
C19 C20 C15 C14 177.4(3) . . . . ?
C16 C15 C14 O3 133.4(3) . . . . ?
C20 C15 C14 O3 -42.4(3) . . . . ?
C16 C15 C14 C5 -47.2(3) . . . . ?
C20 C15 C14 C5 137.0(3) . . . . ?
C8 C13 C12 C11 0.6(4) . . . . ?
C13 C12 C11 C10 0.2(5) . . . . ?
C12 C11 C10 C9 -0.3(6) . . . . ?
C5 S1 C2 N1 -179.2(2) . . . . ?
C5 S1 C2 C3 -1.3(2) . . . . ?
N1 C2 C3 C4 179.1(3) . . . . ?
S1 C2 C3 C4 1.4(3) . . . . ?
N1 C2 C3 C6 -7.0(7) . . . . ?
S1 C2 C3 C6 175.3(6) . . . . ?
N1 C2 C3 C6B 11.1(8) . . . . ?
S1 C2 C3 C6B -166.6(7) . . . . ?
O1 C6 C3 C2 28.2(15) . . . . ?
O2 C6 C3 C2 -172.9(7) . . . . ?
O1 C6 C3 C4 -159.0(9) . . . . ?
O2 C6 C3 C4 0.0(13) . . . . ?
O1B C6B C3 C2 -37.4(16) . . . . ?
O2B C6B C3 C2 163.3(8) . . . . ?
O1B C6B C3 C4 156.9(10) . . . . ?
O2B C6B C3 C4 -2.4(15) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C6 C3 C4 C5 -174.0(7) . . . . ?
C6B C3 C4 C5 165.6(8) . . . . ?
C2 C3 C4 C8 -179.0(2) . . . . ?
C6 C3 C4 C8 7.7(8) . . . . ?
C6B C3 C4 C8 -12.7(9) . . . . ?
C3 C4 C5 C14 -174.5(3) . . . . ?
C8 C4 C5 C14 3.8(4) . . . . ?
C3 C4 C5 S1 -0.2(3) . . . . ?
C8 C4 C5 S1 178.05(18) . . . . ?
O3 C14 C5 C4 161.7(3) . . . . ?
C15 C14 C5 C4 -17.7(4) . . . . ?
O3 C14 C5 S1 -12.5(3) . . . . ?
C15 C14 C5 S1 168.0(2) . . . . ?
C2 S1 C5 C4 0.9(2) . . . . ?
C2 S1 C5 C14 176.47(19) . . . . ?
C12 C13 C8 C9 -1.4(4) . . . . ?
C12 C13 C8 C4 179.9(2) . . . . ?
C5 C4 C8 C13 -70.2(3) . . . . ?
C3 C4 C8 C13 107.9(3) . . . . ?
C5 C4 C8 C9 111.1(3) . . . . ?
C3 C4 C8 C9 -70.8(3) . . . . ?
C11 C10 C9 C8 -0.5(5) . . . . ?
C13 C8 C9 C10 1.4(5) . . . . ?
C4 C8 C9 C10 -179.9(3) . . . . ?

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
N1 H1N1 O1 0.87(2) 2.17(3) 2.763(16) 125(3) . yes
N1 H1N1 O1 0.87(2) 2.21(3) 2.892(12) 136(3) 5_566 yes
N1 H1N1 O1B 0.87(2) 2.07(3) 2.663(18) 125(3) . yes
N1 H1N1 O1B 0.87(2) 2.35(3) 3.019(15) 134(3) 5_566 yes
N1 H1N2 O3 0.87(2) 1.97(2) 2.829(3) 169(3) 4_466 yes

_refine_diff_density_max         0.123
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.031



_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_3V_1
_database_code_depnum_ccdc_archive 'CCDC 2163445'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2022-04-12 deposited with the CCDC.	2022-04-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
;'5-benzoyl-2-(3-chlorophenyl)-4-phenylthiophene-3-carbonitrile'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H14 Cl N O S'
_chemical_formula_sum            'C24 H14 Cl N O S'
_chemical_formula_weight         399.87

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'
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'
N N 0.0061 0.0033 '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                   7.8592(5)
_cell_length_b                   9.8424(6)
_cell_length_c                   13.5018(8)
_cell_angle_alpha                109.699(2)
_cell_angle_beta                 95.917(2)
_cell_angle_gamma                100.938(2)
_cell_volume                     949.53(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3962
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.68


_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.326
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6443

_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0878 before and 0.0540 after correction.
The Ratio of minimum to maximum transmission is 0.6599.
The λ/2 correction factor is Not present.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            31092
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.684
_diffrn_reflns_theta_max         26.729
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3986
_reflns_number_gt                3291
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0160P)²+1.0226P] 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         3986
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.1016
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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
Cl1 Cl 0.26797(13) -0.11791(9) 0.13469(6) 0.0757(3) Uani 1 1 d . . . . .
O1 O 0.8810(2) 0.6388(2) 0.51264(14) 0.0536(5) Uani 1 1 d . . . . .
N1 N 0.3003(4) 0.2649(4) 0.7482(2) 0.0826(9) Uani 1 1 d . . . . .
S1 S 0.64156(8) 0.35247(7) 0.46971(5) 0.04231(16) Uani 1 1 d . . . . .
C2 C 0.4922(3) 0.2567(3) 0.52156(18) 0.0371(5) Uani 1 1 d . . . . .
C3 C 0.5132(3) 0.3315(3) 0.63021(18) 0.0386(5) Uani 1 1 d . . . . .
C4 C 0.6554(3) 0.4622(3) 0.67370(18) 0.0374(5) Uani 1 1 d . . . . .
C5 C 0.7371(3) 0.4865(2) 0.59341(18) 0.0373(5) Uani 1 1 d . . . . .
C6 C 0.3717(3) 0.1155(3) 0.44930(19) 0.0385(5) Uani 1 1 d . . . . .
C7 C 0.3742(3) 0.0680(3) 0.34013(19) 0.0431(5) Uani 1 1 d . . . . .
H7 H 0.452136 0.124719 0.313657 0.052 Uiso 1 1 calc R U . . .
C8 C 0.2613(3) -0.0632(3) 0.2709(2) 0.0476(6) Uani 1 1 d . . . . .
C9 C 0.1441(3) -0.1507(3) 0.3069(2) 0.0499(6) Uani 1 1 d . . . . .
H9 H 0.067047 -0.237752 0.259395 0.060 Uiso 1 1 calc R U . . .
C10 C 0.1444(3) -0.1055(3) 0.4150(2) 0.0550(7) Uani 1 1 d . . . . .
H10 H 0.067766 -0.164146 0.440816 0.066 Uiso 1 1 calc R U . . .
C11 C 0.2557(3) 0.0248(3) 0.4859(2) 0.0500(6) Uani 1 1 d . . . . .
H11 H 0.253569 0.052575 0.558707 0.060 Uiso 1 1 calc R U . . .
C12 C 0.3951(3) 0.2928(3) 0.6961(2) 0.0527(7) Uani 1 1 d . . . . .
C13 C 0.7025(3) 0.5558(3) 0.78892(18) 0.0388(5) Uani 1 1 d . . . . .
C14 C 0.7340(3) 0.7090(3) 0.8255(2) 0.0470(6) Uani 1 1 d . . . . .
H14 H 0.722085 0.756031 0.776777 0.056 Uiso 1 1 calc R U . . .
C15 C 0.7831(4) 0.7933(3) 0.9336(2) 0.0616(7) Uani 1 1 d . . . . .
H15 H 0.805390 0.896373 0.956965 0.074 Uiso 1 1 calc R U . . .
C16 C 0.7989(4) 0.7255(4) 1.0065(2) 0.0700(9) Uani 1 1 d . . . . .
H16 H 0.831477 0.782313 1.079135 0.084 Uiso 1 1 calc R U . . .
C17 C 0.7664(5) 0.5739(4) 0.9718(2) 0.0767(10) Uani 1 1 d . . . . .
H17 H 0.776482 0.527728 1.021197 0.092 Uiso 1 1 calc R U . . .
C18 C 0.7188(4) 0.4888(3) 0.8640(2) 0.0581(7) Uani 1 1 d . . . . .
H18 H 0.697518 0.385810 0.841377 0.070 Uiso 1 1 calc R U . . .
C19 C 0.8824(3) 0.6066(2) 0.59231(18) 0.0380(5) Uani 1 1 d . . . . .
C20 C 1.0291(3) 0.6819(3) 0.68519(18) 0.0394(5) Uani 1 1 d . . . . .
C21 C 1.1023(3) 0.8332(3) 0.7132(2) 0.0496(6) Uani 1 1 d . . . . .
H21 H 1.055765 0.885818 0.675956 0.060 Uiso 1 1 calc R U . . .
C22 C 1.2438(4) 0.9049(3) 0.7962(2) 0.0633(8) Uani 1 1 d . . . . .
H22 H 1.290764 1.006423 0.816115 0.076 Uiso 1 1 calc R U . . .
C23 C 1.3151(4) 0.8265(4) 0.8494(2) 0.0696(9) Uani 1 1 d . . . . .
H23 H 1.410750 0.875188 0.905162 0.084 Uiso 1 1 calc R U . . .
C24 C 1.2462(4) 0.6762(4) 0.8210(2) 0.0638(8) Uani 1 1 d . . . . .
H24 H 1.296985 0.623432 0.856491 0.077 Uiso 1 1 calc R U . . .
C25 C 1.1014(3) 0.6039(3) 0.7397(2) 0.0477(6) Uani 1 1 d . . . . .
H25 H 1.052774 0.503025 0.721712 0.057 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
Cl1 C8 1.743(3) . ?
O1 C19 1.219(3) . ?
N1 C12 1.134(3) . ?
S1 C2 1.718(2) . ?
S1 C5 1.724(2) . ?
C2 C3 1.377(3) . ?
C2 C6 1.475(3) . ?
C3 C4 1.435(3) . ?
C3 C12 1.437(3) . ?
C4 C5 1.380(3) . ?
C4 C13 1.480(3) . ?
C5 C19 1.485(3) . ?
C6 C7 1.392(3) . ?
C6 C11 1.398(3) . ?
C7 C8 1.382(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(3) . ?
C9 C10 1.374(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C13 C14 1.382(3) . ?
C13 C18 1.391(3) . ?
C14 C15 1.384(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.368(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.484(3) . ?
C20 C25 1.384(3) . ?
C20 C21 1.393(3) . ?
C21 C22 1.379(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.371(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.378(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.384(4) . ?
C24 H24 0.9300 . ?
C25 H25 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
C2 S1 C5 93.09(11) . . ?
C3 C2 C6 131.5(2) . . ?
C3 C2 S1 109.52(17) . . ?
C6 C2 S1 118.99(17) . . ?
C2 C3 C4 115.02(19) . . ?
C2 C3 C12 124.0(2) . . ?
C4 C3 C12 120.8(2) . . ?
C5 C4 C3 110.4(2) . . ?
C5 C4 C13 126.3(2) . . ?
C3 C4 C13 123.36(19) . . ?
C4 C5 C19 133.0(2) . . ?
C4 C5 S1 111.91(17) . . ?
C19 C5 S1 115.02(16) . . ?
C7 C6 C11 117.9(2) . . ?
C7 C6 C2 119.3(2) . . ?
C11 C6 C2 122.8(2) . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 121.7(2) . . ?
C9 C8 Cl1 119.6(2) . . ?
C7 C8 Cl1 118.67(19) . . ?
C10 C9 C8 118.1(2) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C9 C10 C11 121.5(2) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C6 120.5(2) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
N1 C12 C3 178.4(3) . . ?
C14 C13 C18 118.1(2) . . ?
C14 C13 C4 122.4(2) . . ?
C18 C13 C4 119.4(2) . . ?
C13 C14 C15 120.9(2) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.5(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 120.6(3) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
O1 C19 C20 120.9(2) . . ?
O1 C19 C5 118.7(2) . . ?
C20 C19 C5 120.36(19) . . ?
C25 C20 C21 119.6(2) . . ?
C25 C20 C19 121.6(2) . . ?
C21 C20 C19 118.7(2) . . ?
C22 C21 C20 120.0(3) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 119.9(3) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C25 119.9(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C20 C25 C24 119.9(3) . . ?
C20 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?

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
C5 S1 C2 C3 2.52(18) . . . . ?
C5 S1 C2 C6 -176.35(18) . . . . ?
C6 C2 C3 C4 175.5(2) . . . . ?
S1 C2 C3 C4 -3.1(3) . . . . ?
C6 C2 C3 C12 -9.8(4) . . . . ?
S1 C2 C3 C12 171.5(2) . . . . ?
C2 C3 C4 C5 2.2(3) . . . . ?
C12 C3 C4 C5 -172.6(2) . . . . ?
C2 C3 C4 C13 -178.4(2) . . . . ?
C12 C3 C4 C13 6.7(3) . . . . ?
C3 C4 C5 C19 176.6(2) . . . . ?
C13 C4 C5 C19 -2.8(4) . . . . ?
C3 C4 C5 S1 -0.2(2) . . . . ?
C13 C4 C5 S1 -179.55(18) . . . . ?
C2 S1 C5 C4 -1.34(18) . . . . ?
C2 S1 C5 C19 -178.73(17) . . . . ?
C3 C2 C6 C7 177.5(2) . . . . ?
S1 C2 C6 C7 -3.9(3) . . . . ?
C3 C2 C6 C11 -3.7(4) . . . . ?
S1 C2 C6 C11 174.92(19) . . . . ?
C11 C6 C7 C8 1.7(3) . . . . ?
C2 C6 C7 C8 -179.4(2) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C6 C7 C8 Cl1 179.58(18) . . . . ?
C7 C8 C9 C10 -1.3(4) . . . . ?
Cl1 C8 C9 C10 179.0(2) . . . . ?
C8 C9 C10 C11 1.3(4) . . . . ?
C9 C10 C11 C6 0.3(4) . . . . ?
C7 C6 C11 C10 -1.7(4) . . . . ?
C2 C6 C11 C10 179.4(2) . . . . ?
C5 C4 C13 C14 46.1(3) . . . . ?
C3 C4 C13 C14 -133.2(2) . . . . ?
C5 C4 C13 C18 -132.9(3) . . . . ?
C3 C4 C13 C18 47.8(3) . . . . ?
C18 C13 C14 C15 1.0(4) . . . . ?
C4 C13 C14 C15 -178.0(2) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C14 C15 C16 C17 0.2(5) . . . . ?
C15 C16 C17 C18 0.3(6) . . . . ?
C16 C17 C18 C13 -0.2(5) . . . . ?
C14 C13 C18 C17 -0.5(4) . . . . ?
C4 C13 C18 C17 178.6(3) . . . . ?
C4 C5 C19 O1 -148.3(3) . . . . ?
S1 C5 C19 O1 28.3(3) . . . . ?
C4 C5 C19 C20 33.7(4) . . . . ?
S1 C5 C19 C20 -149.65(18) . . . . ?
O1 C19 C20 C25 -138.0(2) . . . . ?
C5 C19 C20 C25 40.0(3) . . . . ?
O1 C19 C20 C21 37.8(3) . . . . ?
C5 C19 C20 C21 -144.2(2) . . . . ?
C25 C20 C21 C22 -1.3(4) . . . . ?
C19 C20 C21 C22 -177.2(2) . . . . ?
C20 C21 C22 C23 1.6(4) . . . . ?
C21 C22 C23 C24 -0.3(5) . . . . ?
C22 C23 C24 C25 -1.4(5) . . . . ?
C21 C20 C25 C24 -0.4(4) . . . . ?
C19 C20 C25 C24 175.4(2) . . . . ?
C23 C24 C25 C20 1.7(4) . . . . ?

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.051





_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_NTT001
_database_code_depnum_ccdc_archive 'CCDC 2166476'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2022-04-14 deposited with the CCDC.	2022-04-15 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_NTT001              
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Poor crystals obtained for this compound weakly diffracted
on a copper rotating anode and intensities recorded on an IP were barely 
seen beyond atomic resolution incitating us to apply a resolution cutoff
of 1.08 Angstroms.  
 
;
_vrf_PLAT089_NTT001              
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       2.85 Note  
RESPONSE: as a consequence of resolution cutoff
;
_vrf_PLAT340_NTT001              
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0255 Ang.  
RESPONSE:  direct consequences of poor diffraction
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
;'(5-amino-3-phenylthiophene-2,4-diyl)bis(phenylmethanone)'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H17 N O2 S'
_chemical_formula_sum            'C24 H17 N O2 S'
_chemical_formula_weight         383.44

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   34.351(3)
_cell_length_b                   11.9372(10)
_cell_length_c                   9.5653(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3922.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4730
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      71.1

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             1600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    1.615
_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  0.524
_exptl_absorpt_process_details   'Abscorr (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  'OSMIC CMF Confocal'
_diffrn_detector                 'Rapid 2 IP'
_diffrn_measurement_device       
;
Crystal Goniometer chi partial
;
_diffrn_measurement_device_type  
;
Rigaku Rapid2 mm007HF
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            17849
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.573
_diffrn_reflns_theta_max         45.538
_diffrn_reflns_theta_full        45.538
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3232
_reflns_number_gt                2404
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.986

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_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          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.21(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3221
_refine_ls_number_parameters     616
_refine_ls_number_restraints     1189
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0964
_refine_ls_wR_factor_ref         0.2675
_refine_ls_wR_factor_gt          0.2528
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      0.968
_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_1 S 0.2948(3) 0.1114(13) 0.4628(10) 0.104(3) Uani 0.523(14) 1 d D U P A 1
C2_1 C 0.2919(6) 0.0599(8) 0.2890(19) 0.094(6) Uani 0.523(14) 1 d D U P A 1
C3_1 C 0.3258(8) 0.0442(15) 0.2146(19) 0.085(6) Uani 0.523(14) 1 d D U P A 1
C4_1 C 0.3583(5) 0.075(2) 0.301(4) 0.080(5) Uani 0.523(14) 1 d D U P A 1
C5_1 C 0.3456(6) 0.111(2) 0.430(2) 0.091(5) Uani 0.523(14) 1 d D U P A 1
N1_1 N 0.2542(7) 0.0421(17) 0.253(3) 0.111(8) Uani 0.523(14) 1 d D U P A 1
H1A_1 H 0.248551 0.016707 0.171790 0.134 Uiso 0.523(14) 1 calc R U P A 1
H1B_1 H 0.235990 0.056124 0.312488 0.134 Uiso 0.523(14) 1 calc R U P A 1
S1B_1 S 0.2819(3) 0.0510(7) 0.2548(13) 0.105(4) Uani 0.477(14) 1 d D U P A 2
C2B_1 C 0.3006(8) 0.101(6) 0.416(4) 0.106(6) Uani 0.477(14) 1 d D U P A 2
C3B_1 C 0.3403(8) 0.098(3) 0.438(2) 0.094(5) Uani 0.477(14) 1 d D U P A 2
C4B_1 C 0.3586(5) 0.053(3) 0.314(4) 0.085(5) Uani 0.477(14) 1 d D U P A 2
C5B_1 C 0.3309(7) 0.013(2) 0.223(3) 0.078(5) Uani 0.477(14) 1 d D U P A 2
N1B_1 N 0.2732(8) 0.123(3) 0.512(4) 0.149(11) Uani 0.477(14) 1 d D U P A 2
H1BA_1 H 0.279755 0.138362 0.596445 0.179 Uiso 0.477(14) 1 calc R U P A 2
H1BB_1 H 0.249014 0.123096 0.488279 0.179 Uiso 0.477(14) 1 calc R U P A 2
C6_1 C 0.3293(4) -0.0109(12) 0.0737(17) 0.092(4) Uani 1 1 d D U . . .
O2_1 O 0.3001(3) -0.0035(10) -0.0085(18) 0.128(4) Uani 1 1 d . . . . .
O1_1 O 0.3452(3) 0.1530(11) 0.6697(15) 0.133(4) Uani 1 1 d . . . . .
C7_1 C 0.3642(5) -0.0721(14) 0.020(2) 0.101(4) Uani 1 1 d . . . . .
C8_1 C 0.3759(5) -0.0537(16) -0.120(2) 0.119(5) Uani 1 1 d . . . . .
H8_1 H 0.361889 -0.006272 -0.178827 0.142 Uiso 1 1 calc R U . . .
C9_1 C 0.4077(6) -0.1068(19) -0.166(3) 0.144(7) Uani 1 1 d . . . . .
H9_1 H 0.416347 -0.091127 -0.256450 0.173 Uiso 1 1 calc R U . . .
C10_1 C 0.4283(6) -0.1820(15) -0.090(2) 0.122(5) Uani 1 1 d . . . . .
H10_1 H 0.450852 -0.214017 -0.125578 0.146 Uiso 1 1 calc R U . . .
C11_1 C 0.4153(6) -0.2102(15) 0.041(2) 0.121(5) Uani 1 1 d . . . . .
H11_1 H 0.427394 -0.267113 0.090961 0.145 Uiso 1 1 calc R U . . .
C12_1 C 0.3838(4) -0.1525(12) 0.097(2) 0.098(4) Uani 1 1 d . . . . .
H12_1 H 0.375807 -0.168189 0.188120 0.118 Uiso 1 1 calc R U . . .
C13_1 C 0.4002(4) 0.0587(11) 0.2742(18) 0.086(4) Uani 1 1 d D U . . .
C14_1 C 0.4242(5) -0.0031(15) 0.357(2) 0.115(6) Uani 1 1 d . . . . .
H14_1 H 0.414228 -0.044469 0.431537 0.138 Uiso 1 1 calc R U . . .
C15_1 C 0.4652(6) -0.0031(18) 0.327(2) 0.128(7) Uani 1 1 d . . . . .
H15_1 H 0.482791 -0.039608 0.385762 0.154 Uiso 1 1 calc R U . . .
C16_1 C 0.4774(6) 0.051(3) 0.212(3) 0.162(9) Uani 1 1 d . . . . .
H16_1 H 0.503637 0.046423 0.189781 0.195 Uiso 1 1 calc R U . . .
C17_1 C 0.4550(5) 0.1117(19) 0.129(3) 0.138(7) Uani 1 1 d . . . . .
H17_1 H 0.465236 0.151099 0.053372 0.166 Uiso 1 1 calc R U . . .
C18_1 C 0.4153(4) 0.1133(14) 0.1594(19) 0.106(5) Uani 1 1 d . . . . .
H18_1 H 0.398525 0.152257 0.100576 0.128 Uiso 1 1 calc R U . . .
C19_1 C 0.3624(5) 0.1512(14) 0.5564(18) 0.106(4) Uani 1 1 d D U . . .
C20_1 C 0.4012(4) 0.2024(12) 0.552(2) 0.100(4) Uani 1 1 d . . . . .
C21_1 C 0.4129(5) 0.2723(13) 0.444(2) 0.120(6) Uani 1 1 d . . . . .
H21_1 H 0.395877 0.284213 0.369923 0.144 Uiso 1 1 calc R U . . .
C22_1 C 0.4474(5) 0.3232(16) 0.442(3) 0.131(6) Uani 1 1 d . . . . .
H22_1 H 0.453475 0.369537 0.367267 0.157 Uiso 1 1 calc R U . . .
C23_1 C 0.4740(6) 0.3101(17) 0.545(3) 0.133(6) Uani 1 1 d . . . . .
H23_1 H 0.498137 0.345042 0.541173 0.159 Uiso 1 1 calc R U . . .
C24_1 C 0.4635(6) 0.2413(16) 0.659(3) 0.133(6) Uani 1 1 d . . . . .
H24_1 H 0.481067 0.230948 0.731814 0.159 Uiso 1 1 calc R U . . .
C25_1 C 0.4274(5) 0.1888(12) 0.664(2) 0.114(5) Uani 1 1 d . . . . .
H25_1 H 0.420674 0.144907 0.740173 0.137 Uiso 1 1 calc R U . . .
S1_2 S 0.46632(14) 0.5453(9) 0.7549(9) 0.102(2) Uani 0.796(12) 1 d D U P B 1
C2_2 C 0.4496(5) 0.5971(9) 0.6009(17) 0.102(5) Uani 0.796(12) 1 d D U P B 1
C3_2 C 0.4092(5) 0.5982(14) 0.5869(16) 0.084(5) Uani 0.796(12) 1 d D U P B 1
C4_2 C 0.3918(4) 0.554(2) 0.710(2) 0.081(4) Uani 0.796(12) 1 d D U P B 1
C5_2 C 0.4200(4) 0.5223(16) 0.8076(18) 0.091(4) Uani 0.796(12) 1 d D U P B 1
N1_2 N 0.4740(5) 0.6331(15) 0.5035(19) 0.115(6) Uani 0.796(12) 1 d D U P B 1
H1A_2 H 0.465083 0.659222 0.426048 0.138 Uiso 0.796(12) 1 calc R U P B 1
H1B_2 H 0.498666 0.630434 0.517778 0.138 Uiso 0.796(12) 1 calc R U P B 1
S1B_2 S 0.4540(5) 0.6108(15) 0.562(2) 0.092(6) Uani 0.204(12) 1 d D U P B 2
C2B_2 C 0.4611(10) 0.558(14) 0.726(8) 0.096(7) Uani 0.204(12) 1 d D U P B 2
C3B_2 C 0.4273(11) 0.526(7) 0.798(5) 0.093(6) Uani 0.204(12) 1 d D U P B 2
C4B_2 C 0.3938(7) 0.558(9) 0.718(7) 0.085(6) Uani 0.204(12) 1 d D U P B 2
C5B_2 C 0.4060(9) 0.622(8) 0.603(6) 0.086(6) Uani 0.204(12) 1 d D U P B 2
N1B_2 N 0.4975(13) 0.532(5) 0.763(7) 0.093(13) Uani 0.204(12) 1 d D U P B 2
H1BA_2 H 0.501525 0.491525 0.836028 0.112 Uiso 0.204(12) 1 calc R U P B 2
H1BB_2 H 0.516772 0.554530 0.713269 0.112 Uiso 0.204(12) 1 calc R U P B 2
O2_2 O 0.4497(3) 0.4709(12) 1.0112(16) 0.135(5) Uani 1 1 d . . . . .
C6_2 C 0.3889(4) 0.6501(12) 0.4670(18) 0.094(4) Uani 1 1 d D U . . .
O7_2 O 0.4066(3) 0.6506(11) 0.3543(15) 0.126(4) Uani 1 1 d . . . . .
C7_2 C 0.3501(4) 0.7047(12) 0.4764(19) 0.093(4) Uani 1 1 d . . . . .
C8_2 C 0.3251(5) 0.6982(14) 0.360(2) 0.115(5) Uani 1 1 d . . . . .
H8_2 H 0.333518 0.660529 0.280571 0.138 Uiso 1 1 calc R U . . .
C9_2 C 0.2891(5) 0.7449(14) 0.360(2) 0.118(6) Uani 1 1 d . . . . .
H9_2 H 0.272309 0.736512 0.284927 0.142 Uiso 1 1 calc R U . . .
C10_2 C 0.2782(5) 0.8060(17) 0.478(3) 0.132(6) Uani 1 1 d . . . . .
H10_2 H 0.253800 0.839596 0.480443 0.158 Uiso 1 1 calc R U . . .
C11_2 C 0.3017(5) 0.8176(15) 0.587(3) 0.120(6) Uani 1 1 d . . . . .
H11_2 H 0.293306 0.860120 0.662434 0.144 Uiso 1 1 calc R U . . .
C12_2 C 0.3388(4) 0.7681(12) 0.592(2) 0.102(5) Uani 1 1 d . . . . .
H12_2 H 0.355043 0.777105 0.668964 0.122 Uiso 1 1 calc R U . . .
C13_2 C 0.3502(4) 0.5372(12) 0.7345(18) 0.084(4) Uani 1 1 d D U . . .
C14_2 C 0.3278(4) 0.4794(15) 0.643(2) 0.104(5) Uani 1 1 d . . . . .
H14_2 H 0.339541 0.452683 0.561845 0.125 Uiso 1 1 calc R U . . .
C15_2 C 0.2901(5) 0.4584(16) 0.661(3) 0.125(6) Uani 1 1 d . . . . .
H15_2 H 0.276803 0.412831 0.598330 0.149 Uiso 1 1 calc R U . . .
C16_2 C 0.2712(5) 0.5033(16) 0.771(2) 0.118(6) Uani 1 1 d . . . . .
H16_2 H 0.244610 0.491596 0.782081 0.141 Uiso 1 1 calc R U . . .
C17_2 C 0.2921(5) 0.5682(15) 0.868(2) 0.109(5) Uani 1 1 d . . . . .
H17_2 H 0.279358 0.597843 0.945345 0.131 Uiso 1 1 calc R U . . .
C18_2 C 0.3312(4) 0.5880(13) 0.850(2) 0.099(4) Uani 1 1 d . . . . .
H18_2 H 0.344792 0.633790 0.911266 0.119 Uiso 1 1 calc R U . . .
C19_2 C 0.4188(5) 0.4686(14) 0.9431(18) 0.109(4) Uani 1 1 d D U . . .
C20_2 C 0.3836(4) 0.4135(14) 1.001(2) 0.099(4) Uani 1 1 d . . . . .
C21_2 C 0.3722(5) 0.4379(15) 1.136(2) 0.110(5) Uani 1 1 d . . . . .
H21_2 H 0.387616 0.483493 1.191837 0.132 Uiso 1 1 calc R U . . .
C22_2 C 0.3385(5) 0.3953(16) 1.186(2) 0.117(5) Uani 1 1 d . . . . .
H22_2 H 0.329430 0.419127 1.272511 0.140 Uiso 1 1 calc R U . . .
C24_2 C 0.3296(5) 0.2883(15) 0.975(2) 0.115(5) Uani 1 1 d . . . . .
H24_2 H 0.315693 0.238021 0.919959 0.138 Uiso 1 1 calc R U . . .
C25_2 C 0.3622(4) 0.3360(12) 0.925(2) 0.100(5) Uani 1 1 d . . . . .
H25_2 H 0.370754 0.316169 0.836615 0.120 Uiso 1 1 calc R U . . .
C23_2 C 0.3167(6) 0.3143(17) 1.109(3) 0.133(6) Uani 1 1 d . . . . .
H23_2 H 0.294654 0.280509 1.146353 0.160 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_1 C5_1 1.77(2) . ?
S1_1 C2_1 1.77(2) . ?
C2_1 N1_1 1.36(3) . ?
C2_1 C3_1 1.38(3) . ?
C3_1 C4_1 1.44(4) . ?
C3_1 C6_1 1.50(2) . ?
C4_1 C5_1 1.38(3) . ?
C4_1 C13_1 1.476(18) . ?
C5_1 C19_1 1.42(2) . ?
S1B_1 C5B_1 1.77(2) . ?
S1B_1 C2B_1 1.78(2) . ?
C2B_1 N1B_1 1.34(3) . ?
C2B_1 C3B_1 1.38(3) . ?
C3B_1 C4B_1 1.44(4) . ?
C3B_1 C19_1 1.50(2) . ?
C4B_1 C5B_1 1.38(3) . ?
C4B_1 C13_1 1.48(2) . ?
C5B_1 C6_1 1.45(2) . ?
C6_1 O2_1 1.276(17) . ?
C6_1 C7_1 1.49(2) . ?
O1_1 C19_1 1.234(18) . ?
C7_1 C12_1 1.38(2) . ?
C7_1 C8_1 1.42(3) . ?
C8_1 C9_1 1.34(3) . ?
C9_1 C10_1 1.36(3) . ?
C10_1 C11_1 1.37(3) . ?
C11_1 C12_1 1.39(2) . ?
C13_1 C14_1 1.36(2) . ?
C13_1 C18_1 1.38(2) . ?
C14_1 C15_1 1.44(2) . ?
C15_1 C16_1 1.35(3) . ?
C16_1 C17_1 1.32(3) . ?
C17_1 C18_1 1.40(2) . ?
C19_1 C20_1 1.47(2) . ?
C20_1 C21_1 1.39(2) . ?
C20_1 C25_1 1.41(2) . ?
C21_1 C22_1 1.33(2) . ?
C22_1 C23_1 1.35(3) . ?
C23_1 C24_1 1.41(3) . ?
C24_1 C25_1 1.39(2) . ?
S1_2 C5_2 1.691(16) . ?
S1_2 C2_2 1.697(17) . ?
C2_2 N1_2 1.32(2) . ?
C2_2 C3_2 1.39(2) . ?
C3_2 C4_2 1.42(3) . ?
C3_2 C6_2 1.477(19) . ?
C4_2 C5_2 1.40(2) . ?
C4_2 C13_2 1.462(17) . ?
C5_2 C19_2 1.45(2) . ?
S1B_2 C5B_2 1.70(2) . ?
S1B_2 C2B_2 1.702(19) . ?
C2B_2 N1B_2 1.34(3) . ?
C2B_2 C3B_2 1.40(2) . ?
C3B_2 C4B_2 1.43(3) . ?
C3B_2 C19_2 1.58(3) . ?
C4B_2 C5B_2 1.40(2) . ?
C4B_2 C13_2 1.52(2) . ?
C5B_2 C6_2 1.47(4) . ?
O2_2 C19_2 1.244(17) . ?
C6_2 O7_2 1.237(18) . ?
C6_2 C7_2 1.49(2) . ?
C7_2 C8_2 1.41(2) . ?
C7_2 C12_2 1.39(2) . ?
C8_2 C9_2 1.36(2) . ?
C9_2 C10_2 1.39(3) . ?
C10_2 C11_2 1.32(3) . ?
C11_2 C12_2 1.41(2) . ?
C13_2 C14_2 1.36(2) . ?
C13_2 C18_2 1.42(2) . ?
C14_2 C15_2 1.33(2) . ?
C15_2 C16_2 1.34(3) . ?
C16_2 C17_2 1.41(3) . ?
C17_2 C18_2 1.37(2) . ?
C19_2 C20_2 1.49(2) . ?
C20_2 C21_2 1.38(2) . ?
C20_2 C25_2 1.39(2) . ?
C21_2 C22_2 1.35(2) . ?
C22_2 C23_2 1.43(3) . ?
C24_2 C25_2 1.34(2) . ?
C24_2 C23_2 1.39(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
C5_1 S1_1 C2_1 83.8(10) . . ?
N1_1 C2_1 C3_1 131(2) . . ?
N1_1 C2_1 S1_1 110.1(19) . . ?
C3_1 C2_1 S1_1 118.9(14) . . ?
C2_1 C3_1 C4_1 108.9(13) . . ?
C2_1 C3_1 C6_1 126.1(18) . . ?
C4_1 C3_1 C6_1 124.5(16) . . ?
C5_1 C4_1 C3_1 110.6(12) . . ?
C5_1 C4_1 C13_1 120(2) . . ?
C3_1 C4_1 C13_1 128.4(19) . . ?
C4_1 C5_1 C19_1 137.6(18) . . ?
C4_1 C5_1 S1_1 117.8(13) . . ?
C19_1 C5_1 S1_1 104.6(13) . . ?
C5B_1 S1B_1 C2B_1 83.7(11) . . ?
N1B_1 C2B_1 C3B_1 127(3) . . ?
N1B_1 C2B_1 S1B_1 114(3) . . ?
C3B_1 C2B_1 S1B_1 118.7(14) . . ?
C2B_1 C3B_1 C4B_1 108.5(14) . . ?
C2B_1 C3B_1 C19_1 126.9(19) . . ?
C4B_1 C3B_1 C19_1 123.7(18) . . ?
C5B_1 C4B_1 C3B_1 110.4(12) . . ?
C5B_1 C4B_1 C13_1 121(2) . . ?
C3B_1 C4B_1 C13_1 128(2) . . ?
C4B_1 C5B_1 C6_1 136(2) . . ?
C4B_1 C5B_1 S1B_1 117.3(13) . . ?
C6_1 C5B_1 S1B_1 100.6(14) . . ?
O2_1 C6_1 C5B_1 128.4(17) . . ?
O2_1 C6_1 C3_1 117.4(17) . . ?
O2_1 C6_1 C7_1 116.9(15) . . ?
C5B_1 C6_1 C7_1 113.6(16) . . ?
C3_1 C6_1 C7_1 125.7(16) . . ?
C12_1 C7_1 C8_1 118.2(17) . . ?
C12_1 C7_1 C6_1 123.2(17) . . ?
C8_1 C7_1 C6_1 118.4(17) . . ?
C9_1 C8_1 C7_1 118(2) . . ?
C8_1 C9_1 C10_1 124(2) . . ?
C9_1 C10_1 C11_1 119(2) . . ?
C10_1 C11_1 C12_1 119.1(19) . . ?
C11_1 C12_1 C7_1 121.0(17) . . ?
C14_1 C13_1 C18_1 119.5(15) . . ?
C14_1 C13_1 C4_1 124.2(19) . . ?
C18_1 C13_1 C4_1 116.2(18) . . ?
C14_1 C13_1 C4B_1 114(2) . . ?
C18_1 C13_1 C4B_1 126(2) . . ?
C13_1 C14_1 C15_1 119(2) . . ?
C16_1 C15_1 C14_1 118(2) . . ?
C17_1 C16_1 C15_1 125(2) . . ?
C16_1 C17_1 C18_1 117(2) . . ?
C13_1 C18_1 C17_1 122.0(18) . . ?
O1_1 C19_1 C5_1 123.9(17) . . ?
O1_1 C19_1 C20_1 117.0(15) . . ?
C5_1 C19_1 C20_1 119.0(16) . . ?
O1_1 C19_1 C3B_1 115.3(18) . . ?
C20_1 C19_1 C3B_1 127.7(18) . . ?
C21_1 C20_1 C25_1 116.7(16) . . ?
C21_1 C20_1 C19_1 122.4(18) . . ?
C25_1 C20_1 C19_1 120.8(16) . . ?
C22_1 C21_1 C20_1 123(2) . . ?
C21_1 C22_1 C23_1 123(2) . . ?
C22_1 C23_1 C24_1 117(2) . . ?
C23_1 C24_1 C25_1 121(2) . . ?
C20_1 C25_1 C24_1 120(2) . . ?
C5_2 S1_2 C2_2 90.0(9) . . ?
N1_2 C2_2 C3_2 123.9(15) . . ?
N1_2 C2_2 S1_2 121.0(13) . . ?
C3_2 C2_2 S1_2 115.1(13) . . ?
C2_2 C3_2 C4_2 109.6(12) . . ?
C2_2 C3_2 C6_2 123.2(15) . . ?
C4_2 C3_2 C6_2 126.8(13) . . ?
C5_2 C4_2 C3_2 111.3(10) . . ?
C5_2 C4_2 C13_2 121.9(15) . . ?
C3_2 C4_2 C13_2 126.7(13) . . ?
C4_2 C5_2 C19_2 134.5(15) . . ?
C4_2 C5_2 S1_2 114.0(12) . . ?
C19_2 C5_2 S1_2 111.4(12) . . ?
C5B_2 S1B_2 C2B_2 87.6(15) . . ?
N1B_2 C2B_2 C3B_2 126(5) . . ?
N1B_2 C2B_2 S1B_2 118(4) . . ?
C3B_2 C2B_2 S1B_2 115.4(19) . . ?
C2B_2 C3B_2 C4B_2 109.6(14) . . ?
C2B_2 C3B_2 C19_2 135(2) . . ?
C4B_2 C3B_2 C19_2 116(3) . . ?
C5B_2 C4B_2 C3B_2 108.6(14) . . ?
C5B_2 C4B_2 C13_2 118(3) . . ?
C3B_2 C4B_2 C13_2 134(3) . . ?
C4B_2 C5B_2 C6_2 134(5) . . ?
C4B_2 C5B_2 S1B_2 115.1(19) . . ?
C6_2 C5B_2 S1B_2 101(2) . . ?
O7_2 C6_2 C5B_2 125.5(18) . . ?
O7_2 C6_2 C3_2 116.6(14) . . ?
O7_2 C6_2 C7_2 119.3(13) . . ?
C5B_2 C6_2 C7_2 114(2) . . ?
C3_2 C6_2 C7_2 124.0(15) . . ?
C8_2 C7_2 C12_2 119.1(14) . . ?
C8_2 C7_2 C6_2 118.4(16) . . ?
C12_2 C7_2 C6_2 122.3(15) . . ?
C9_2 C8_2 C7_2 122.1(19) . . ?
C8_2 C9_2 C10_2 118(2) . . ?
C11_2 C10_2 C9_2 122(2) . . ?
C10_2 C11_2 C12_2 122(2) . . ?
C11_2 C12_2 C7_2 116.8(17) . . ?
C14_2 C13_2 C18_2 117.2(13) . . ?
C14_2 C13_2 C4_2 121.4(17) . . ?
C18_2 C13_2 C4_2 121.2(17) . . ?
C14_2 C13_2 C4B_2 125(4) . . ?
C18_2 C13_2 C4B_2 118(4) . . ?
C15_2 C14_2 C13_2 124(2) . . ?
C14_2 C15_2 C16_2 120(2) . . ?
C15_2 C16_2 C17_2 119.3(17) . . ?
C18_2 C17_2 C16_2 120.6(18) . . ?
C17_2 C18_2 C13_2 118.4(17) . . ?
O2_2 C19_2 C5_2 115.9(16) . . ?
O2_2 C19_2 C20_2 120.5(15) . . ?
C5_2 C19_2 C20_2 123.6(15) . . ?
O2_2 C19_2 C3B_2 107(2) . . ?
C20_2 C19_2 C3B_2 132(2) . . ?
C21_2 C20_2 C25_2 118.6(18) . . ?
C21_2 C20_2 C19_2 119.1(17) . . ?
C25_2 C20_2 C19_2 122.2(17) . . ?
C22_2 C21_2 C20_2 119.7(19) . . ?
C21_2 C22_2 C23_2 121(2) . . ?
C25_2 C24_2 C23_2 120(2) . . ?
C24_2 C25_2 C20_2 122.8(19) . . ?
C24_2 C23_2 C22_2 117(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
C5_1 S1_1 C2_1 N1_1 179.8(4) . . . . ?
C5_1 S1_1 C2_1 C3_1 0.0(3) . . . . ?
N1_1 C2_1 C3_1 C4_1 -179.7(5) . . . . ?
S1_1 C2_1 C3_1 C4_1 0.0(3) . . . . ?
N1_1 C2_1 C3_1 C6_1 -7.3(16) . . . . ?
S1_1 C2_1 C3_1 C6_1 172.4(16) . . . . ?
C2_1 C3_1 C4_1 C5_1 -0.1(7) . . . . ?
C6_1 C3_1 C4_1 C5_1 -172.6(16) . . . . ?
C2_1 C3_1 C4_1 C13_1 171(2) . . . . ?
C6_1 C3_1 C4_1 C13_1 -2(2) . . . . ?
C3_1 C4_1 C5_1 C19_1 180(2) . . . . ?
C13_1 C4_1 C5_1 C19_1 8(2) . . . . ?
C3_1 C4_1 C5_1 S1_1 0.1(8) . . . . ?
C13_1 C4_1 C5_1 S1_1 -172(2) . . . . ?
C2_1 S1_1 C5_1 C4_1 -0.1(6) . . . . ?
C2_1 S1_1 C5_1 C19_1 -179.9(17) . . . . ?
C5B_1 S1B_1 C2B_1 N1B_1 -166(6) . . . . ?
C5B_1 S1B_1 C2B_1 C3B_1 5(5) . . . . ?
N1B_1 C2B_1 C3B_1 C4B_1 171(6) . . . . ?
S1B_1 C2B_1 C3B_1 C4B_1 1(6) . . . . ?
N1B_1 C2B_1 C3B_1 C19_1 -19(10) . . . . ?
S1B_1 C2B_1 C3B_1 C19_1 170(3) . . . . ?
C2B_1 C3B_1 C4B_1 C5B_1 -8(4) . . . . ?
C19_1 C3B_1 C4B_1 C5B_1 -178(3) . . . . ?
C2B_1 C3B_1 C4B_1 C13_1 164(5) . . . . ?
C19_1 C3B_1 C4B_1 C13_1 -6(5) . . . . ?
C3B_1 C4B_1 C5B_1 C6_1 159(3) . . . . ?
C13_1 C4B_1 C5B_1 C6_1 -14(5) . . . . ?
C3B_1 C4B_1 C5B_1 S1B_1 13(4) . . . . ?
C13_1 C4B_1 C5B_1 S1B_1 -160(3) . . . . ?
C2B_1 S1B_1 C5B_1 C4B_1 -10(3) . . . . ?
C2B_1 S1B_1 C5B_1 C6_1 -167(3) . . . . ?
C4B_1 C5B_1 C6_1 O2_1 -148(3) . . . . ?
S1B_1 C5B_1 C6_1 O2_1 2(3) . . . . ?
C4B_1 C5B_1 C6_1 C7_1 44(4) . . . . ?
S1B_1 C5B_1 C6_1 C7_1 -165.9(13) . . . . ?
C2_1 C3_1 C6_1 O2_1 29(2) . . . . ?
C4_1 C3_1 C6_1 O2_1 -159.3(12) . . . . ?
C2_1 C3_1 C6_1 C7_1 -151.6(15) . . . . ?
C4_1 C3_1 C6_1 C7_1 20(2) . . . . ?
O2_1 C6_1 C7_1 C12_1 -133.1(16) . . . . ?
C5B_1 C6_1 C7_1 C12_1 36(2) . . . . ?
C3_1 C6_1 C7_1 C12_1 48(2) . . . . ?
O2_1 C6_1 C7_1 C8_1 42(2) . . . . ?
C5B_1 C6_1 C7_1 C8_1 -149.5(19) . . . . ?
C3_1 C6_1 C7_1 C8_1 -137.4(18) . . . . ?
C12_1 C7_1 C8_1 C9_1 -7(3) . . . . ?
C6_1 C7_1 C8_1 C9_1 178.4(17) . . . . ?
C7_1 C8_1 C9_1 C10_1 4(3) . . . . ?
C8_1 C9_1 C10_1 C11_1 3(3) . . . . ?
C9_1 C10_1 C11_1 C12_1 -7(3) . . . . ?
C8_1 C7_1 C12_1 C11_1 3(2) . . . . ?
C6_1 C7_1 C12_1 C11_1 177.6(15) . . . . ?
C10_1 C11_1 C12_1 C7_1 4(3) . . . . ?
C5_1 C4_1 C13_1 C14_1 51(2) . . . . ?
C3_1 C4_1 C13_1 C14_1 -119(2) . . . . ?
C5_1 C4_1 C13_1 C18_1 -126.8(16) . . . . ?
C3_1 C4_1 C13_1 C18_1 63(2) . . . . ?
C5B_1 C4B_1 C13_1 C14_1 -120(3) . . . . ?
C3B_1 C4B_1 C13_1 C14_1 68(4) . . . . ?
C5B_1 C4B_1 C13_1 C18_1 56(4) . . . . ?
C3B_1 C4B_1 C13_1 C18_1 -116(3) . . . . ?
C18_1 C13_1 C14_1 C15_1 4(2) . . . . ?
C4_1 C13_1 C14_1 C15_1 -174(2) . . . . ?
C4B_1 C13_1 C14_1 C15_1 -180(2) . . . . ?
C13_1 C14_1 C15_1 C16_1 -5(3) . . . . ?
C14_1 C15_1 C16_1 C17_1 5(4) . . . . ?
C15_1 C16_1 C17_1 C18_1 -4(4) . . . . ?
C14_1 C13_1 C18_1 C17_1 -3(2) . . . . ?
C4_1 C13_1 C18_1 C17_1 174.8(19) . . . . ?
C4B_1 C13_1 C18_1 C17_1 -179(2) . . . . ?
C16_1 C17_1 C18_1 C13_1 3(3) . . . . ?
C4_1 C5_1 C19_1 O1_1 -161.8(17) . . . . ?
S1_1 C5_1 C19_1 O1_1 18(2) . . . . ?
C4_1 C5_1 C19_1 C20_1 23(3) . . . . ?
S1_1 C5_1 C19_1 C20_1 -156.7(13) . . . . ?
C2B_1 C3B_1 C19_1 O1_1 34(5) . . . . ?
C4B_1 C3B_1 C19_1 O1_1 -158(3) . . . . ?
C2B_1 C3B_1 C19_1 C20_1 -145(4) . . . . ?
C4B_1 C3B_1 C19_1 C20_1 23(4) . . . . ?
O1_1 C19_1 C20_1 C21_1 -135.7(18) . . . . ?
C5_1 C19_1 C20_1 C21_1 39(2) . . . . ?
C3B_1 C19_1 C20_1 C21_1 43(3) . . . . ?
O1_1 C19_1 C20_1 C25_1 40(2) . . . . ?
C5_1 C19_1 C20_1 C25_1 -145.4(18) . . . . ?
C3B_1 C19_1 C20_1 C25_1 -142(2) . . . . ?
C25_1 C20_1 C21_1 C22_1 1(2) . . . . ?
C19_1 C20_1 C21_1 C22_1 176.8(17) . . . . ?
C20_1 C21_1 C22_1 C23_1 0(3) . . . . ?
C21_1 C22_1 C23_1 C24_1 -1(3) . . . . ?
C22_1 C23_1 C24_1 C25_1 0(3) . . . . ?
C23_1 C24_1 C25_1 C20_1 1(3) . . . . ?
C21_1 C20_1 C25_1 C24_1 -2(2) . . . . ?
C19_1 C20_1 C25_1 C24_1 -177.8(15) . . . . ?
C5_2 S1_2 C2_2 N1_2 -179.9(5) . . . . ?
C5_2 S1_2 C2_2 C3_2 0.2(3) . . . . ?
N1_2 C2_2 C3_2 C4_2 -179.9(5) . . . . ?
S1_2 C2_2 C3_2 C4_2 0.1(3) . . . . ?
N1_2 C2_2 C3_2 C6_2 -6.1(15) . . . . ?
S1_2 C2_2 C3_2 C6_2 173.8(15) . . . . ?
C2_2 C3_2 C4_2 C5_2 -0.4(7) . . . . ?
C6_2 C3_2 C4_2 C5_2 -173.8(16) . . . . ?
C2_2 C3_2 C4_2 C13_2 -177(2) . . . . ?
C6_2 C3_2 C4_2 C13_2 9(2) . . . . ?
C3_2 C4_2 C5_2 C19_2 -176(2) . . . . ?
C13_2 C4_2 C5_2 C19_2 1(2) . . . . ?
C3_2 C4_2 C5_2 S1_2 0.5(8) . . . . ?
C13_2 C4_2 C5_2 S1_2 178(2) . . . . ?
C2_2 S1_2 C5_2 C4_2 -0.4(6) . . . . ?
C2_2 S1_2 C5_2 C19_2 177.0(15) . . . . ?
C5B_2 S1B_2 C2B_2 N1B_2 -179(14) . . . . ?
C5B_2 S1B_2 C2B_2 C3B_2 14(10) . . . . ?
N1B_2 C2B_2 C3B_2 C4B_2 -172(14) . . . . ?
S1B_2 C2B_2 C3B_2 C4B_2 -6(13) . . . . ?
N1B_2 C2B_2 C3B_2 C19_2 9(23) . . . . ?
S1B_2 C2B_2 C3B_2 C19_2 176(8) . . . . ?
C2B_2 C3B_2 C4B_2 C5B_2 -8(10) . . . . ?
C19_2 C3B_2 C4B_2 C5B_2 171(7) . . . . ?
C2B_2 C3B_2 C4B_2 C13_2 174(13) . . . . ?
C19_2 C3B_2 C4B_2 C13_2 -7(13) . . . . ?
C3B_2 C4B_2 C5B_2 C6_2 158(9) . . . . ?
C13_2 C4B_2 C5B_2 C6_2 -23(12) . . . . ?
C3B_2 C4B_2 C5B_2 S1B_2 19(8) . . . . ?
C13_2 C4B_2 C5B_2 S1B_2 -163(8) . . . . ?
C2B_2 S1B_2 C5B_2 C4B_2 -19(7) . . . . ?
C2B_2 S1B_2 C5B_2 C6_2 -170(9) . . . . ?
C4B_2 C5B_2 C6_2 O7_2 -136(6) . . . . ?
S1B_2 C5B_2 C6_2 O7_2 7(7) . . . . ?
C4B_2 C5B_2 C6_2 C7_2 57(9) . . . . ?
S1B_2 C5B_2 C6_2 C7_2 -159(3) . . . . ?
C2_2 C3_2 C6_2 O7_2 30(2) . . . . ?
C4_2 C3_2 C6_2 O7_2 -157.6(13) . . . . ?
C2_2 C3_2 C6_2 C7_2 -147.5(13) . . . . ?
C4_2 C3_2 C6_2 C7_2 25(2) . . . . ?
O7_2 C6_2 C7_2 C12_2 -139.8(16) . . . . ?
C5B_2 C6_2 C7_2 C12_2 27(4) . . . . ?
C3_2 C6_2 C7_2 C12_2 37(2) . . . . ?
O7_2 C6_2 C7_2 C8_2 36(2) . . . . ?
C5B_2 C6_2 C7_2 C8_2 -157(4) . . . . ?
C3_2 C6_2 C7_2 C8_2 -147.0(15) . . . . ?
C12_2 C7_2 C8_2 C9_2 -5(2) . . . . ?
C6_2 C7_2 C8_2 C9_2 179.5(15) . . . . ?
C7_2 C8_2 C9_2 C10_2 4(3) . . . . ?
C8_2 C9_2 C10_2 C11_2 -1(3) . . . . ?
C9_2 C10_2 C11_2 C12_2 -1(3) . . . . ?
C8_2 C7_2 C12_2 C11_2 3(2) . . . . ?
C6_2 C7_2 C12_2 C11_2 178.5(14) . . . . ?
C10_2 C11_2 C12_2 C7_2 0(3) . . . . ?
C5_2 C4_2 C13_2 C14_2 -124.6(16) . . . . ?
C3_2 C4_2 C13_2 C14_2 52(2) . . . . ?
C5_2 C4_2 C13_2 C18_2 61(2) . . . . ?
C3_2 C4_2 C13_2 C18_2 -122.6(16) . . . . ?
C5B_2 C4B_2 C13_2 C14_2 64(8) . . . . ?
C3B_2 C4B_2 C13_2 C14_2 -118(9) . . . . ?
C5B_2 C4B_2 C13_2 C18_2 -112(6) . . . . ?
C3B_2 C4B_2 C13_2 C18_2 67(11) . . . . ?
C18_2 C13_2 C14_2 C15_2 -7(2) . . . . ?
C4_2 C13_2 C14_2 C15_2 178.2(18) . . . . ?
C4B_2 C13_2 C14_2 C15_2 177(3) . . . . ?
C13_2 C14_2 C15_2 C16_2 6(3) . . . . ?
C14_2 C15_2 C16_2 C17_2 -3(3) . . . . ?
C15_2 C16_2 C17_2 C18_2 2(3) . . . . ?
C16_2 C17_2 C18_2 C13_2 -3(2) . . . . ?
C14_2 C13_2 C18_2 C17_2 5(2) . . . . ?
C4_2 C13_2 C18_2 C17_2 -179.6(15) . . . . ?
C4B_2 C13_2 C18_2 C17_2 -178(3) . . . . ?
C4_2 C5_2 C19_2 O2_2 -167.9(14) . . . . ?
S1_2 C5_2 C19_2 O2_2 15(2) . . . . ?
C4_2 C5_2 C19_2 C20_2 12(3) . . . . ?
S1_2 C5_2 C19_2 C20_2 -164.7(14) . . . . ?
C2B_2 C3B_2 C19_2 O2_2 13(13) . . . . ?
C4B_2 C3B_2 C19_2 O2_2 -165(6) . . . . ?
C2B_2 C3B_2 C19_2 C20_2 -164(11) . . . . ?
C4B_2 C3B_2 C19_2 C20_2 18(9) . . . . ?
O2_2 C19_2 C20_2 C21_2 48(2) . . . . ?
C5_2 C19_2 C20_2 C21_2 -131.6(18) . . . . ?
C3B_2 C19_2 C20_2 C21_2 -135(5) . . . . ?
O2_2 C19_2 C20_2 C25_2 -130.1(17) . . . . ?
C5_2 C19_2 C20_2 C25_2 50(2) . . . . ?
C3B_2 C19_2 C20_2 C25_2 47(5) . . . . ?
C25_2 C20_2 C21_2 C22_2 -7(2) . . . . ?
C19_2 C20_2 C21_2 C22_2 174.7(15) . . . . ?
C20_2 C21_2 C22_2 C23_2 8(3) . . . . ?
C23_2 C24_2 C25_2 C20_2 -2(2) . . . . ?
C21_2 C20_2 C25_2 C24_2 4(2) . . . . ?
C19_2 C20_2 C25_2 C24_2 -177.8(15) . . . . ?
C25_2 C24_2 C23_2 C22_2 2(2) . . . . ?
C21_2 C22_2 C23_2 C24_2 -5(3) . . . . ?

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
N1_1 H1A_1 S1_1 0.86 2.74 3.35(3) 129.9 4_554 yes
N1_1 H1A_1 O2_1 0.86 2.48 3.01(4) 120.2 . yes
N1_1 H1B_1 O2_1 0.86 2.23 2.99(3) 147.9 4 yes
N1B_1 H1BA_1 O1_1 0.86 2.36 2.92(4) 123.0 . yes
N1B_1 H1BB_1 O2_1 0.86 2.27 2.94(4) 136.0 4 yes
N1_2 H1A_2 O7_2 0.86 2.13 2.727(19) 126.6 . y
N1_2 H1B_2 O2_2 0.86 2.15 2.903(18) 146.2 2_664 yes
N1B_2 H1BA2 S1B_2 0.86 2.92 3.73(6) 157.3 2_665 yes
N1B_2 H1BA_2 O2_2 0.86 2.46 2.98(8) 119.5 . yes
N1B_2 H1BB_2 O2_2 0.86 2.27 3.02(7) 144.9 2_664 yes


_refine_diff_density_max         0.725
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.066





_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Deuterated chloroform'
