# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_RG13
_database_code_depnum_ccdc_archive 'CCDC 2006655'
loop_
_audit_author_name
_audit_author_address
'Thierry ROISNEL'
;CDIFX ISCR CNRS Univ Rennes
France
;
_audit_update_record             
;
2020-05-29 deposited with the CCDC.	2021-09-16 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 30 avril 2019                                            #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H20 N3 S, Br, H2 O'
_chemical_formula_sum            'C23 H22 Br N3 O S'
_chemical_formula_weight         468.40
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                            UNIT CELL INFORMATION                             #
#------------------------------------------------------------------------------#


_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0870(10)
_cell_length_b                   10.0635(13)
_cell_length_c                   13.3909(17)
_cell_angle_alpha                80.956(4)
_cell_angle_beta                 81.422(4)
_cell_angle_gamma                65.230(4)
_cell_volume                     1093.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9840
_cell_measurement_theta_min      2.2413
_cell_measurement_theta_max      27.6809
_cell_measurement_wavelength     0.71073

#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.130
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             480
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.592
_exptl_absorpt_correction_T_max  0.772

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_diffrn_reflns_av_r_equivalents  0.0365
_diffrn_reflns_av_uneti/neti     0.0306
_diffrn_reflns_number            21379
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.241
_diffrn_reflns_theta_max         27.539
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.977
_reflns_number_total             4926
_reflns_number_gt                4380
_reflns_threshold_expression     >2sigma(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.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0082P)²+1.2468P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         4926
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0595
_refine_ls_wR_factor_gt          0.0557
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.068

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
Br Br -0.2901 2.4595 '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'
S S 0.1246 0.1234 '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'

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 0.20870(5) 0.28554(5) 0.47510(3) 0.01671(9) Uani 1 1 d . . . . .
C1 C 0.1234(2) 0.41346(19) 0.37432(13) 0.0172(3) Uani 1 1 d . . . . .
H1 H 0.012641 0.447525 0.361761 0.021 Uiso 1 1 calc R U . . .
C2 C 0.2300(2) 0.45923(19) 0.31603(13) 0.0151(3) Uani 1 1 d . . . . .
C3 C 0.1957(2) 0.5671(2) 0.22478(13) 0.0169(3) Uani 1 1 d . . . . .
C4 C 0.2876(2) 0.5347(2) 0.13177(14) 0.0230(4) Uani 1 1 d . . . . .
H4 H 0.378800 0.443196 0.126733 0.028 Uiso 1 1 calc R U . . .
C5 C 0.2461(3) 0.6361(2) 0.04657(15) 0.0296(5) Uani 1 1 d . . . . .
H5 H 0.308360 0.613395 -0.016829 0.035 Uiso 1 1 calc R U . . .
C6 C 0.1141(3) 0.7705(2) 0.05350(16) 0.0331(5) Uani 1 1 d . . . . .
H6 H 0.086098 0.839611 -0.004997 0.040 Uiso 1 1 calc R U . . .
C7 C 0.0236(3) 0.8035(2) 0.14558(17) 0.0355(5) Uani 1 1 d . . . . .
H7 H -0.066272 0.895890 0.150509 0.043 Uiso 1 1 calc R U . . .
C8 C 0.0634(2) 0.7021(2) 0.23105(15) 0.0263(4) Uani 1 1 d . . . . .
H8 H 0.000044 0.725107 0.294089 0.032 Uiso 1 1 calc R U . . .
N9 N 0.38740(17) 0.38990(15) 0.35110(11) 0.0135(3) Uani 1 1 d . . . . .
C10 C 0.5257(2) 0.42242(19) 0.30690(12) 0.0137(3) Uani 1 1 d . . . . .
C11 C 0.5200(2) 0.5615(2) 0.30980(14) 0.0184(4) Uani 1 1 d . . . . .
H11 H 0.426776 0.635192 0.340522 0.022 Uiso 1 1 calc R U . . .
C12 C 0.6537(2) 0.5911(2) 0.26681(14) 0.0216(4) Uani 1 1 d . . . . .
H12 H 0.651903 0.685870 0.268044 0.026 Uiso 1 1 calc R U . . .
C13 C 0.7895(2) 0.4830(2) 0.22217(13) 0.0209(4) Uani 1 1 d . . . . .
H13 H 0.879721 0.504297 0.191969 0.025 Uiso 1 1 calc R U . . .
C14 C 0.7936(2) 0.3439(2) 0.22163(14) 0.0213(4) Uani 1 1 d . . . . .
H14 H 0.887724 0.269484 0.192244 0.026 Uiso 1 1 calc R U . . .
C15 C 0.6611(2) 0.3127(2) 0.26380(13) 0.0173(3) Uani 1 1 d . . . . .
H15 H 0.663210 0.217699 0.263085 0.021 Uiso 1 1 calc R U . . .
C16 C 0.3917(2) 0.29708(19) 0.43538(13) 0.0148(3) Uani 1 1 d . . . . .
N17 N 0.52456(19) 0.21804(17) 0.48458(11) 0.0170(3) Uani 1 1 d . . . . .
H17 H 0.612(3) 0.233(2) 0.4737(16) 0.020 Uiso 1 1 d . U . . .
N18 N 0.49790(18) 0.13859(16) 0.57500(11) 0.0161(3) Uani 1 1 d . . . . .
C19 C 0.6235(2) 0.0640(2) 0.62363(14) 0.0189(4) Uani 1 1 d . . . . .
H19 H 0.726990 0.060082 0.594437 0.023 Uiso 1 1 calc R U . . .
C20 C 0.6097(2) -0.01510(19) 0.72351(14) 0.0187(4) Uani 1 1 d . . . . .
C21 C 0.7463(3) -0.0798(3) 0.77823(16) 0.0338(5) Uani 1 1 d . . . . .
H21 H 0.846514 -0.076094 0.748845 0.041 Uiso 1 1 calc R U . . .
C22 C 0.7364(3) -0.1498(3) 0.87558(17) 0.0365(5) Uani 1 1 d . . . . .
H22 H 0.830803 -0.194024 0.911624 0.044 Uiso 1 1 calc R U . . .
C23 C 0.5929(3) -0.1564(2) 0.92102(14) 0.0248(4) Uani 1 1 d . . . . .
C24 C 0.4569(3) -0.0924(2) 0.86570(15) 0.0245(4) Uani 1 1 d . . . . .
H24 H 0.357072 -0.096880 0.895252 0.029 Uiso 1 1 calc R U . . .
C25 C 0.4646(2) -0.0223(2) 0.76826(14) 0.0213(4) Uani 1 1 d . . . . .
H25 H 0.370388 0.020794 0.732055 0.026 Uiso 1 1 calc R U . . .
C26 C 0.5833(3) -0.2303(2) 1.02752(15) 0.0337(5) Uani 1 1 d . . . . .
H26A H 0.590548 -0.329619 1.024635 0.051 Uiso 1 1 calc R U . . .
H26B H 0.479675 -0.172792 1.064394 0.051 Uiso 1 1 calc R U . . .
H26C H 0.673545 -0.236583 1.062672 0.051 Uiso 1 1 calc R U . . .
Br1 Br 0.84394(2) 0.28265(2) 0.49974(2) 0.02010(6) Uani 1 1 d . . . . .
O1W O 0.9152(2) 0.00954(19) 0.35171(14) 0.0412(4) Uani 1 1 d . . . . .
H1WA H 0.901(3) 0.081(3) 0.386(2) 0.049 Uiso 1 1 d . U . . .
H1WB H 0.973(4) -0.068(3) 0.388(2) 0.049 Uiso 1 1 d . U . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C16 1.7149(18) . ?
S1 C1 1.7346(18) . ?
C1 C2 1.340(3) . ?
C1 H1 0.9500 . ?
C2 N9 1.419(2) . ?
C2 C3 1.477(2) . ?
C3 C8 1.391(3) . ?
C3 C4 1.395(3) . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.380(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
N9 C16 1.341(2) . ?
N9 C10 1.449(2) . ?
C10 C15 1.384(2) . ?
C10 C11 1.385(2) . ?
C11 C12 1.391(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 N17 1.339(2) . ?
N17 N18 1.391(2) . ?
N17 H17 0.86(2) . ?
N18 C19 1.281(2) . ?
C19 C20 1.462(2) . ?
C19 H19 0.9500 . ?
C20 C25 1.391(3) . ?
C20 C21 1.395(3) . ?
C21 C22 1.390(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.379(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.395(3) . ?
C23 C26 1.509(3) . ?
C24 C25 1.389(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
O1W H1WA 0.86(3) . ?
O1W H1WB 0.86(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
C16 S1 C1 89.38(8) . . ?
C2 C1 S1 113.01(13) . . ?
C2 C1 H1 123.5 . . ?
S1 C1 H1 123.5 . . ?
C1 C2 N9 111.96(15) . . ?
C1 C2 C3 126.23(16) . . ?
N9 C2 C3 121.80(15) . . ?
C8 C3 C4 119.25(17) . . ?
C8 C3 C2 118.86(16) . . ?
C4 C3 C2 121.83(16) . . ?
C5 C4 C3 120.04(18) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 120.32(19) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 119.86(19) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.2(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C3 120.32(19) . . ?
C7 C8 H8 119.8 . . ?
C3 C8 H8 119.8 . . ?
C16 N9 C2 112.15(14) . . ?
C16 N9 C10 122.98(14) . . ?
C2 N9 C10 124.71(14) . . ?
C15 C10 C11 121.72(17) . . ?
C15 C10 N9 118.93(15) . . ?
C11 C10 N9 119.35(15) . . ?
C10 C11 C12 118.64(17) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C13 C12 C11 120.40(18) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 119.98(18) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.36(17) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 118.89(17) . . ?
C10 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
N17 C16 N9 124.53(16) . . ?
N17 C16 S1 121.97(13) . . ?
N9 C16 S1 113.49(12) . . ?
C16 N17 N18 114.68(15) . . ?
C16 N17 H17 124.0(15) . . ?
N18 N17 H17 118.9(15) . . ?
C19 N18 N17 115.38(15) . . ?
N18 C19 C20 120.84(17) . . ?
N18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C25 C20 C21 118.69(17) . . ?
C25 C20 C19 122.91(16) . . ?
C21 C20 C19 118.33(17) . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 121.52(19) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C22 C23 C24 117.98(18) . . ?
C22 C23 C26 120.89(19) . . ?
C24 C23 C26 121.1(2) . . ?
C25 C24 C23 121.29(19) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C20 120.25(17) . . ?
C24 C25 H25 119.9 . . ?
C20 C25 H25 119.9 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
H1WA O1W H1WB 104(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
C16 S1 C1 C2 0.09(14) . . . . ?
S1 C1 C2 N9 0.60(19) . . . . ?
S1 C1 C2 C3 179.91(14) . . . . ?
C1 C2 C3 C8 51.3(3) . . . . ?
N9 C2 C3 C8 -129.51(19) . . . . ?
C1 C2 C3 C4 -125.9(2) . . . . ?
N9 C2 C3 C4 53.3(2) . . . . ?
C8 C3 C4 C5 -0.6(3) . . . . ?
C2 C3 C4 C5 176.59(18) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C5 C6 C7 C8 -0.6(4) . . . . ?
C6 C7 C8 C3 0.6(4) . . . . ?
C4 C3 C8 C7 0.0(3) . . . . ?
C2 C3 C8 C7 -177.3(2) . . . . ?
C1 C2 N9 C16 -1.2(2) . . . . ?
C3 C2 N9 C16 179.45(15) . . . . ?
C1 C2 N9 C10 -176.66(15) . . . . ?
C3 C2 N9 C10 4.0(2) . . . . ?
C16 N9 C10 C15 68.0(2) . . . . ?
C2 N9 C10 C15 -116.98(18) . . . . ?
C16 N9 C10 C11 -111.25(19) . . . . ?
C2 N9 C10 C11 63.7(2) . . . . ?
C15 C10 C11 C12 0.9(3) . . . . ?
N9 C10 C11 C12 -179.84(15) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 -1.0(3) . . . . ?
C12 C13 C14 C15 1.3(3) . . . . ?
C11 C10 C15 C14 -0.6(3) . . . . ?
N9 C10 C15 C14 -179.89(15) . . . . ?
C13 C14 C15 C10 -0.5(3) . . . . ?
C2 N9 C16 N17 -179.64(16) . . . . ?
C10 N9 C16 N17 -4.1(3) . . . . ?
C2 N9 C16 S1 1.29(18) . . . . ?
C10 N9 C16 S1 176.83(12) . . . . ?
C1 S1 C16 N17 -179.91(16) . . . . ?
C1 S1 C16 N9 -0.80(14) . . . . ?
N9 C16 N17 N18 174.78(15) . . . . ?
S1 C16 N17 N18 -6.2(2) . . . . ?
C16 N17 N18 C19 -179.07(16) . . . . ?
N17 N18 C19 C20 175.21(16) . . . . ?
N18 C19 C20 C25 4.2(3) . . . . ?
N18 C19 C20 C21 -172.48(19) . . . . ?
C25 C20 C21 C22 -0.1(3) . . . . ?
C19 C20 C21 C22 176.8(2) . . . . ?
C20 C21 C22 C23 -0.5(4) . . . . ?
C21 C22 C23 C24 0.9(3) . . . . ?
C21 C22 C23 C26 -178.8(2) . . . . ?
C22 C23 C24 C25 -0.8(3) . . . . ?
C26 C23 C24 C25 178.99(18) . . . . ?
C23 C24 C25 C20 0.2(3) . . . . ?
C21 C20 C25 C24 0.2(3) . . . . ?
C19 C20 C25 C24 -176.48(18) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


####################################################################### 
# 
# 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_RG2
_database_code_depnum_ccdc_archive 'CCDC 2006657'
loop_
_audit_author_name
_audit_author_address
'Thierry ROISNEL'
;CDIFX ISCR CNRS Univ Rennes
France
;
_audit_update_record             
;
2020-05-29 deposited with the CCDC.	2021-09-16 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 29 avril 2019                                            #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H20 N3 O S, Br'
_chemical_formula_sum            'C23 H20 Br N3 O S'
_chemical_formula_weight         466.39
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#------------------------------------------------------------------------------#
#                            UNIT CELL INFORMATION                             #
#------------------------------------------------------------------------------#


_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
_space_group_IT_number           43
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'-x, -y, z'
'x, y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'-x, -y+1/2, z+1/2'
'x+1/2, y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'-x+1/2, -y, z+1/2'
'x+1/2, y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
'-x+1/2, -y+1/2, z'

_cell_length_a                   24.627(3)
_cell_length_b                   40.014(4)
_cell_length_c                   9.3291(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9193.2(18)
_cell_formula_units_Z            16
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9332
_cell_measurement_theta_min      2.3894
_cell_measurement_theta_max      27.4664
_cell_measurement_wavelength     0.71073

#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.190
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             3808
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.548
_exptl_absorpt_correction_T_max  0.697

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_diffrn_reflns_av_r_equivalents  0.0387
_diffrn_reflns_av_uneti/neti     0.0395
_diffrn_reflns_number            29030
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -51
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.389
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             5182
_reflns_number_gt                4943
_reflns_threshold_expression     >2sigma(I)
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_max     0.964
_reflns_Friedel_fraction_full    0.961

_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.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0239P)²+15.2430P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         5182
_refine_ls_number_parameters     267
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0664
_refine_ls_wR_factor_gt          0.0655
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.780
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.026(7)

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.41090(3) 0.72363(2) 0.28763(9) 0.01681(17) Uani 1 1 d . . . . .
C1 C 0.46201(13) 0.69651(8) 0.2326(3) 0.0183(6) Uani 1 1 d . . . . .
H1 H 0.469874 0.691745 0.135009 0.022 Uiso 1 1 calc R U . . .
C2 C 0.48888(12) 0.68319(8) 0.3424(3) 0.0157(6) Uani 1 1 d . . . . .
C3 C 0.53360(12) 0.65842(8) 0.3305(3) 0.0150(6) Uani 1 1 d . . . . .
C4 C 0.52125(14) 0.62494(8) 0.3059(4) 0.0212(6) Uani 1 1 d . . . . .
H4 H 0.484457 0.617809 0.306644 0.025 Uiso 1 1 calc R U . . .
C5 C 0.56227(15) 0.60190(9) 0.2804(4) 0.0244(7) Uani 1 1 d . . . . .
H5 H 0.553669 0.579037 0.264995 0.029 Uiso 1 1 calc R U . . .
C6 C 0.61602(14) 0.61249(9) 0.2776(4) 0.0255(7) Uani 1 1 d . . . . .
H6 H 0.644191 0.596997 0.257091 0.031 Uiso 1 1 calc R U . . .
C7 C 0.62844(15) 0.64556(10) 0.3046(5) 0.0297(8) Uani 1 1 d . . . . .
H7 H 0.665320 0.652512 0.304949 0.036 Uiso 1 1 calc R U . . .
C8 C 0.58774(13) 0.66879(9) 0.3312(4) 0.0240(7) Uani 1 1 d . . . . .
H8 H 0.596655 0.691486 0.349692 0.029 Uiso 1 1 calc R U . . .
N9 N 0.46986(10) 0.69463(6) 0.4772(3) 0.0135(5) Uani 1 1 d . . . . .
C10 C 0.49156(12) 0.68412(8) 0.6146(3) 0.0143(5) Uani 1 1 d . . . . .
C11 C 0.53708(13) 0.70005(8) 0.6670(4) 0.0209(6) Uani 1 1 d . . . . .
H11 H 0.553803 0.717621 0.614611 0.025 Uiso 1 1 calc R U . . .
C12 C 0.55802(15) 0.68970(9) 0.7990(4) 0.0259(7) Uani 1 1 d . . . . .
H12 H 0.589059 0.700500 0.837855 0.031 Uiso 1 1 calc R U . . .
C13 C 0.53383(14) 0.66389(9) 0.8731(4) 0.0241(7) Uani 1 1 d . . . . .
H13 H 0.548432 0.656910 0.962452 0.029 Uiso 1 1 calc R U . . .
C14 C 0.48831(13) 0.64804(9) 0.8181(4) 0.0226(7) Uani 1 1 d . . . . .
H14 H 0.471911 0.630239 0.869675 0.027 Uiso 1 1 calc R U . . .
C15 C 0.46665(12) 0.65815(8) 0.6876(4) 0.0186(6) Uani 1 1 d . . . . .
H15 H 0.435413 0.647478 0.649211 0.022 Uiso 1 1 calc R U . . .
C16 C 0.42885(12) 0.71666(8) 0.4637(3) 0.0147(6) Uani 1 1 d . . . . .
N17 N 0.40347(11) 0.73193(7) 0.5717(3) 0.0165(6) Uani 1 1 d . . . . .
H17 H 0.4108(14) 0.7287(9) 0.674(5) 0.020 Uiso 1 1 d . U . . .
N18 N 0.36212(10) 0.75344(6) 0.5276(3) 0.0164(5) Uani 1 1 d . . . . .
C19 C 0.33236(12) 0.76540(7) 0.6288(3) 0.0171(6) Uani 1 1 d . . . . .
H19 H 0.340028 0.759791 0.725632 0.021 Uiso 1 1 calc R U . . .
C20 C 0.28699(12) 0.78748(8) 0.5958(3) 0.0169(6) Uani 1 1 d . . . . .
C21 C 0.25111(13) 0.79607(8) 0.7059(3) 0.0177(6) Uani 1 1 d . . . . .
H21 H 0.257905 0.788334 0.800503 0.021 Uiso 1 1 calc R U . . .
C22 C 0.20563(12) 0.81574(8) 0.6794(4) 0.0177(6) Uani 1 1 d . . . . .
H22 H 0.181415 0.821251 0.755076 0.021 Uiso 1 1 calc R U . . .
C23 C 0.19595(12) 0.82723(7) 0.5413(3) 0.0148(6) Uani 1 1 d . . . . .
C24 C 0.23105(13) 0.81900(8) 0.4293(4) 0.0233(7) Uani 1 1 d . . . . .
H24 H 0.224234 0.826848 0.334878 0.028 Uiso 1 1 calc R U . . .
C25 C 0.27612(14) 0.79914(9) 0.4577(4) 0.0231(7) Uani 1 1 d . . . . .
H25 H 0.299998 0.793394 0.381619 0.028 Uiso 1 1 calc R U . . .
O26 O 0.15061(9) 0.84672(6) 0.5268(3) 0.0208(5) Uani 1 1 d . . . . .
C27 C 0.14222(13) 0.86265(8) 0.3916(4) 0.0219(7) Uani 1 1 d . . . . .
H27A H 0.174674 0.875472 0.365686 0.033 Uiso 1 1 calc R U . . .
H27B H 0.110967 0.877727 0.398104 0.033 Uiso 1 1 calc R U . . .
H27C H 0.135275 0.845659 0.318162 0.033 Uiso 1 1 calc R U . . .
Br1 Br 0.40958(2) 0.73001(2) 0.92018(3) 0.02637(10) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C16 1.724(3) . ?
S1 C1 1.739(3) . ?
C1 C2 1.331(4) . ?
C1 H1 0.9500 . ?
C2 N9 1.418(4) . ?
C2 C3 1.486(4) . ?
C3 C4 1.393(4) . ?
C3 C8 1.397(5) . ?
C4 C5 1.388(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(5) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
N9 C16 1.346(4) . ?
N9 C10 1.451(4) . ?
C10 C11 1.379(4) . ?
C10 C15 1.385(4) . ?
C11 C12 1.398(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 N17 1.334(4) . ?
N17 N18 1.395(4) . ?
N17 H17 0.98(4) . ?
N18 C19 1.287(4) . ?
C19 C20 1.457(4) . ?
C19 H19 0.9500 . ?
C20 C25 1.396(4) . ?
C20 C21 1.398(4) . ?
C21 C22 1.391(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.389(4) . ?
C22 H22 0.9500 . ?
C23 O26 1.369(4) . ?
C23 C24 1.396(4) . ?
C24 C25 1.391(4) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
O26 C27 1.429(4) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 S1 C1 89.71(15) . . ?
C2 C1 S1 112.5(2) . . ?
C2 C1 H1 123.8 . . ?
S1 C1 H1 123.8 . . ?
C1 C2 N9 112.9(3) . . ?
C1 C2 C3 125.3(3) . . ?
N9 C2 C3 121.8(3) . . ?
C4 C3 C8 119.7(3) . . ?
C4 C3 C2 119.5(3) . . ?
C8 C3 C2 120.6(3) . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 120.0(3) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.9(3) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C3 119.3(3) . . ?
C7 C8 H8 120.4 . . ?
C3 C8 H8 120.4 . . ?
C16 N9 C2 112.1(2) . . ?
C16 N9 C10 123.3(2) . . ?
C2 N9 C10 124.6(2) . . ?
C11 C10 C15 122.2(3) . . ?
C11 C10 N9 118.6(3) . . ?
C15 C10 N9 119.2(3) . . ?
C10 C11 C12 118.3(3) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C15 120.1(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 118.6(3) . . ?
C10 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
N17 C16 N9 125.5(3) . . ?
N17 C16 S1 121.7(2) . . ?
N9 C16 S1 112.8(2) . . ?
C16 N17 N18 113.7(3) . . ?
C16 N17 H17 126(2) . . ?
N18 N17 H17 120(2) . . ?
C19 N18 N17 115.4(3) . . ?
N18 C19 C20 120.5(3) . . ?
N18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C25 C20 C21 118.3(3) . . ?
C25 C20 C19 123.0(3) . . ?
C21 C20 C19 118.6(3) . . ?
C22 C21 C20 121.2(3) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C23 C22 C21 119.4(3) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
O26 C23 C22 114.8(3) . . ?
O26 C23 C24 124.5(3) . . ?
C22 C23 C24 120.7(3) . . ?
C25 C24 C23 119.1(3) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C20 121.3(3) . . ?
C24 C25 H25 119.3 . . ?
C20 C25 H25 119.3 . . ?
C23 O26 C27 117.3(2) . . ?
O26 C27 H27A 109.5 . . ?
O26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 S1 C1 C2 1.2(3) . . . . ?
S1 C1 C2 N9 -0.8(4) . . . . ?
S1 C1 C2 C3 178.1(3) . . . . ?
C1 C2 C3 C4 -79.1(4) . . . . ?
N9 C2 C3 C4 99.7(3) . . . . ?
C1 C2 C3 C8 95.3(4) . . . . ?
N9 C2 C3 C8 -85.9(4) . . . . ?
C8 C3 C4 C5 -0.8(5) . . . . ?
C2 C3 C4 C5 173.6(3) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
C4 C5 C6 C7 2.1(6) . . . . ?
C5 C6 C7 C8 -1.6(6) . . . . ?
C6 C7 C8 C3 0.0(6) . . . . ?
C4 C3 C8 C7 1.2(5) . . . . ?
C2 C3 C8 C7 -173.2(3) . . . . ?
C1 C2 N9 C16 -0.3(4) . . . . ?
C3 C2 N9 C16 -179.3(3) . . . . ?
C1 C2 N9 C10 179.7(3) . . . . ?
C3 C2 N9 C10 0.7(5) . . . . ?
C16 N9 C10 C11 -96.1(4) . . . . ?
C2 N9 C10 C11 83.9(4) . . . . ?
C16 N9 C10 C15 85.0(4) . . . . ?
C2 N9 C10 C15 -95.0(4) . . . . ?
C15 C10 C11 C12 -0.8(5) . . . . ?
N9 C10 C11 C12 -179.6(3) . . . . ?
C10 C11 C12 C13 0.8(5) . . . . ?
C11 C12 C13 C14 -0.4(5) . . . . ?
C12 C13 C14 C15 -0.1(5) . . . . ?
C11 C10 C15 C14 0.3(5) . . . . ?
N9 C10 C15 C14 179.1(3) . . . . ?
C13 C14 C15 C10 0.2(5) . . . . ?
C2 N9 C16 N17 -179.0(3) . . . . ?
C10 N9 C16 N17 1.0(5) . . . . ?
C2 N9 C16 S1 1.3(3) . . . . ?
C10 N9 C16 S1 -178.7(2) . . . . ?
C1 S1 C16 N17 178.8(3) . . . . ?
C1 S1 C16 N9 -1.4(3) . . . . ?
N9 C16 N17 N18 -179.6(3) . . . . ?
S1 C16 N17 N18 0.1(4) . . . . ?
C16 N17 N18 C19 171.7(3) . . . . ?
N17 N18 C19 C20 -178.4(3) . . . . ?
N18 C19 C20 C25 -5.7(5) . . . . ?
N18 C19 C20 C21 171.0(3) . . . . ?
C25 C20 C21 C22 0.0(5) . . . . ?
C19 C20 C21 C22 -176.9(3) . . . . ?
C20 C21 C22 C23 -0.5(5) . . . . ?
C21 C22 C23 O26 -179.2(3) . . . . ?
C21 C22 C23 C24 0.6(5) . . . . ?
O26 C23 C24 C25 179.5(3) . . . . ?
C22 C23 C24 C25 -0.2(5) . . . . ?
C23 C24 C25 C20 -0.3(5) . . . . ?
C21 C20 C25 C24 0.4(5) . . . . ?
C19 C20 C25 C24 177.1(3) . . . . ?
C22 C23 O26 C27 172.5(3) . . . . ?
C24 C23 O26 C27 -7.3(4) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: sqz.res
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#

#...............................................................................
# .FAB SHELXL file: sqz.fab
#...............................................................................



# ............... End of .FAB file ........................................... #
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR COMPOUND 3 (RG2)                                       #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################



################################################################################
#                                                                              #
#                            END OF GLOBAL CIF FILE                            #
#                                                                              #
################################################################################

####################################################################### 
# 
# 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_JF680
_database_code_depnum_ccdc_archive 'CCDC 2006656'
loop_
_audit_author_name
_audit_author_address
'Thierry ROISNEL'
;CDIFX ISCR CNRS Univ Rennes
France
;
_audit_update_record             
;
2020-05-29 deposited with the CCDC.	2021-09-16 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 06 mai 2019                                              #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H28 N3 O3 S, Cl'
_chemical_formula_sum            'C20 H28 Cl N3 O3 S'
_chemical_formula_weight         425.96
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                            UNIT CELL INFORMATION                             #
#------------------------------------------------------------------------------#


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.8822(17)
_cell_length_b                   31.959(6)
_cell_length_c                   9.896(2)
_cell_angle_alpha                90
_cell_angle_beta                 121.156(7)
_cell_angle_gamma                90
_cell_volume                     2133.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9700
_cell_measurement_theta_min      2.5493
_cell_measurement_theta_max      27.5257
_cell_measurement_wavelength     0.71073

#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.060
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             904
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_correction_T_max  0.982

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_diffrn_reflns_av_r_equivalents  0.0406
_diffrn_reflns_av_uneti/neti     0.0346
_diffrn_reflns_number            20794
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.488
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_reflns_number_total             4862
_reflns_number_gt                4208
_reflns_threshold_expression     >2sigma(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.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0295P)²+1.9710P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         4862
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0972
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.066

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.76794(6) 0.41610(2) 0.94042(5) 0.01738(10) Uani 1 1 d . . . . .
C1 C 0.6700(2) 0.48087(5) 0.43863(19) 0.0156(3) Uani 1 1 d . . . . .
H1A H 0.809191 0.484514 0.466473 0.019 Uiso 1 1 calc R U . . .
H1B H 0.634449 0.504408 0.484308 0.019 Uiso 1 1 calc R U . . .
C2 C 0.5313(3) 0.47980(6) 0.2585(2) 0.0189(3) Uani 1 1 d . . . . .
H2A H 0.392356 0.476849 0.232163 0.023 Uiso 1 1 calc R U . . .
H2B H 0.542571 0.506410 0.212586 0.023 Uiso 1 1 calc R U . . .
C3 C 0.5844(3) 0.44322(6) 0.1876(2) 0.0203(4) Uani 1 1 d . . . . .
H3A H 0.487527 0.441918 0.072648 0.024 Uiso 1 1 calc R U . . .
H3B H 0.717131 0.448182 0.202633 0.024 Uiso 1 1 calc R U . . .
C4 C 0.5854(3) 0.40135(6) 0.2624(2) 0.0218(4) Uani 1 1 d . . . . .
H4A H 0.635872 0.379290 0.221923 0.026 Uiso 1 1 calc R U . . .
H4B H 0.448049 0.393910 0.231504 0.026 Uiso 1 1 calc R U . . .
C5 C 0.7152(3) 0.40294(5) 0.4432(2) 0.0185(3) Uani 1 1 d . . . . .
H5A H 0.703732 0.376321 0.489065 0.022 Uiso 1 1 calc R U . . .
H5B H 0.855829 0.406977 0.475759 0.022 Uiso 1 1 calc R U . . .
C6 C 0.6453(2) 0.43925(5) 0.50228(18) 0.0136(3) Uani 1 1 d . . . . .
H6 H 0.499377 0.435265 0.454222 0.016 Uiso 1 1 calc R U . . .
N7 N 0.7331(2) 0.43735(4) 0.67680(15) 0.0129(3) Uani 1 1 d . . . . .
C8 C 0.9224(2) 0.45154(5) 0.79557(19) 0.0166(3) Uani 1 1 d . . . . .
C9 C 1.0629(3) 0.47317(6) 0.7604(2) 0.0247(4) Uani 1 1 d . . . . .
H9A H 1.191340 0.476628 0.858263 0.037 Uiso 1 1 calc R U . . .
H9B H 1.009652 0.500702 0.714319 0.037 Uiso 1 1 calc R U . . .
H9C H 1.080159 0.456384 0.685420 0.037 Uiso 1 1 calc R U . . .
C10 C 0.9589(3) 0.44284(5) 0.9406(2) 0.0198(4) Uani 1 1 d . . . . .
H10 H 1.077978 0.450589 1.034463 0.024 Uiso 1 1 calc R U . . .
C11 C 0.6373(2) 0.41747(5) 0.73775(18) 0.0135(3) Uani 1 1 d . . . . .
N12 N 0.4601(2) 0.39911(5) 0.65458(16) 0.0158(3) Uani 1 1 d . . . . .
H12 H 0.377(3) 0.4022(6) 0.551(3) 0.019 Uiso 1 1 d . U . . .
N13 N 0.3897(2) 0.38193(5) 0.74585(17) 0.0177(3) Uani 1 1 d . . . . .
C14 C 0.2335(2) 0.35924(5) 0.6692(2) 0.0168(3) Uani 1 1 d . . . . .
H14 H 0.178795 0.354065 0.559793 0.020 Uiso 1 1 calc R U . . .
C15 C 0.1406(3) 0.34146(5) 0.7510(2) 0.0173(3) Uani 1 1 d . . . . .
C16 C 0.2027(3) 0.35238(6) 0.9062(2) 0.0216(4) Uani 1 1 d . . . . .
H16 H 0.313804 0.370376 0.961955 0.026 Uiso 1 1 calc R U . . .
C17 C 0.1076(3) 0.33784(6) 0.9818(2) 0.0247(4) Uani 1 1 d . . . . .
H17 H 0.155230 0.345201 1.088584 0.030 Uiso 1 1 calc R U . . .
C18 C -0.0583(3) 0.31233(5) 0.8998(2) 0.0231(4) Uani 1 1 d . . . . .
C19 C -0.1230(3) 0.30016(5) 0.7443(2) 0.0220(4) Uani 1 1 d . . . . .
C20 C -0.0218(3) 0.31409(5) 0.6715(2) 0.0187(3) Uani 1 1 d . . . . .
O21 O -0.1709(2) 0.29862(4) 0.95887(18) 0.0310(3) Uani 1 1 d . . . . .
C22 C -0.1002(4) 0.30844(7) 1.1221(3) 0.0390(5) Uani 1 1 d . . . . .
H22A H 0.029785 0.295466 1.189651 0.058 Uiso 1 1 calc R U . . .
H22B H -0.194062 0.297671 1.150521 0.058 Uiso 1 1 calc R U . . .
H22C H -0.088491 0.338856 1.136723 0.058 Uiso 1 1 calc R U . . .
O23 O -0.2842(2) 0.27407(4) 0.66486(18) 0.0283(3) Uani 1 1 d . . . . .
C24 C -0.4629(4) 0.29535(8) 0.5619(4) 0.0700(11) Uani 1 1 d . . . . .
H24A H -0.493682 0.314807 0.622844 0.105 Uiso 1 1 calc R U . . .
H24B H -0.570788 0.275011 0.508167 0.105 Uiso 1 1 calc R U . . .
H24C H -0.448098 0.310970 0.483408 0.105 Uiso 1 1 calc R U . . .
O25 O -0.0853(2) 0.30345(4) 0.51778(15) 0.0273(3) Uani 1 1 d . . . . .
C26 C -0.0836(4) 0.25968(7) 0.4871(3) 0.0409(5) Uani 1 1 d . . . . .
H26A H -0.015698 0.244366 0.587379 0.061 Uiso 1 1 calc R U . . .
H26B H -0.013840 0.255200 0.430261 0.061 Uiso 1 1 calc R U . . .
H26C H -0.220223 0.249524 0.422845 0.061 Uiso 1 1 calc R U . . .
Cl1 Cl 0.12247(6) 0.41312(2) 0.31791(5) 0.02428(11) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C11 1.7169(16) . ?
S1 C10 1.7299(18) . ?
C1 C6 1.527(2) . ?
C1 C2 1.535(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.530(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.527(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.535(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.524(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N7 1.4929(19) . ?
C6 H6 1.0000 . ?
N7 C11 1.345(2) . ?
N7 C8 1.414(2) . ?
C8 C10 1.339(2) . ?
C8 C9 1.492(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 0.9500 . ?
C11 N12 1.335(2) . ?
N12 N13 1.3942(19) . ?
N12 H12 0.89(2) . ?
N13 C14 1.285(2) . ?
C14 C15 1.459(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.393(2) . ?
C15 C20 1.407(2) . ?
C16 C17 1.384(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(3) . ?
C17 H17 0.9500 . ?
C18 O21 1.363(2) . ?
C18 C19 1.402(3) . ?
C19 O23 1.376(2) . ?
C19 C20 1.396(3) . ?
C20 O25 1.376(2) . ?
O21 C22 1.444(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O23 C24 1.414(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O25 C26 1.433(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 S1 C10 89.12(8) . . ?
C6 C1 C2 107.05(13) . . ?
C6 C1 H1A 110.3 . . ?
C2 C1 H1A 110.3 . . ?
C6 C1 H1B 110.3 . . ?
C2 C1 H1B 110.3 . . ?
H1A C1 H1B 108.6 . . ?
C3 C2 C1 110.49(14) . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 112.40(14) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C3 C4 C5 111.66(14) . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C4 108.50(14) . . ?
C6 C5 H5A 110.0 . . ?
C4 C5 H5A 110.0 . . ?
C6 C5 H5B 110.0 . . ?
C4 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
N7 C6 C5 111.68(13) . . ?
N7 C6 C1 115.53(13) . . ?
C5 C6 C1 110.90(14) . . ?
N7 C6 H6 106.0 . . ?
C5 C6 H6 106.0 . . ?
C1 C6 H6 106.0 . . ?
C11 N7 C8 112.01(13) . . ?
C11 N7 C6 120.41(13) . . ?
C8 N7 C6 127.36(13) . . ?
C10 C8 N7 111.93(15) . . ?
C10 C8 C9 124.95(16) . . ?
N7 C8 C9 123.11(15) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 S1 113.39(13) . . ?
C8 C10 H10 123.3 . . ?
S1 C10 H10 123.3 . . ?
N12 C11 N7 125.60(15) . . ?
N12 C11 S1 120.85(12) . . ?
N7 C11 S1 113.53(12) . . ?
C11 N12 N13 114.43(13) . . ?
C11 N12 H12 125.1(13) . . ?
N13 N12 H12 118.8(14) . . ?
C14 N13 N12 114.89(14) . . ?
N13 C14 C15 119.67(16) . . ?
N13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C20 118.09(16) . . ?
C16 C15 C14 121.56(16) . . ?
C20 C15 C14 120.28(16) . . ?
C17 C16 C15 122.13(17) . . ?
C17 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
C16 C17 C18 119.31(17) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
O21 C18 C17 124.20(18) . . ?
O21 C18 C19 115.67(17) . . ?
C17 C18 C19 120.09(17) . . ?
O23 C19 C20 120.26(17) . . ?
O23 C19 C18 119.95(16) . . ?
C20 C19 C18 119.79(16) . . ?
O25 C20 C19 120.90(16) . . ?
O25 C20 C15 118.51(16) . . ?
C19 C20 C15 120.48(16) . . ?
C18 O21 C22 116.73(16) . . ?
O21 C22 H22A 109.5 . . ?
O21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 O23 C24 113.67(15) . . ?
O23 C24 H24A 109.5 . . ?
O23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20 O25 C26 115.93(15) . . ?
O25 C26 H26A 109.5 . . ?
O25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -59.43(18) . . . . ?
C1 C2 C3 C4 54.87(19) . . . . ?
C2 C3 C4 C5 -52.3(2) . . . . ?
C3 C4 C5 C6 54.60(19) . . . . ?
C4 C5 C6 N7 167.52(13) . . . . ?
C4 C5 C6 C1 -62.07(18) . . . . ?
C2 C1 C6 N7 -167.17(13) . . . . ?
C2 C1 C6 C5 64.47(17) . . . . ?
C5 C6 N7 C11 -91.67(18) . . . . ?
C1 C6 N7 C11 140.36(15) . . . . ?
C5 C6 N7 C8 82.48(19) . . . . ?
C1 C6 N7 C8 -45.5(2) . . . . ?
C11 N7 C8 C10 -1.8(2) . . . . ?
C6 N7 C8 C10 -176.33(15) . . . . ?
C11 N7 C8 C9 177.67(16) . . . . ?
C6 N7 C8 C9 3.1(3) . . . . ?
N7 C8 C10 S1 1.3(2) . . . . ?
C9 C8 C10 S1 -178.17(15) . . . . ?
C11 S1 C10 C8 -0.36(15) . . . . ?
C8 N7 C11 N12 -176.83(15) . . . . ?
C6 N7 C11 N12 -1.8(2) . . . . ?
C8 N7 C11 S1 1.51(17) . . . . ?
C6 N7 C11 S1 176.50(11) . . . . ?
C10 S1 C11 N12 177.74(15) . . . . ?
C10 S1 C11 N7 -0.68(13) . . . . ?
N7 C11 N12 N13 -177.79(15) . . . . ?
S1 C11 N12 N13 4.0(2) . . . . ?
C11 N12 N13 C14 -170.75(15) . . . . ?
N12 N13 C14 C15 -176.78(14) . . . . ?
N13 C14 C15 C16 7.7(3) . . . . ?
N13 C14 C15 C20 -175.35(16) . . . . ?
C20 C15 C16 C17 -1.3(3) . . . . ?
C14 C15 C16 C17 175.76(17) . . . . ?
C15 C16 C17 C18 -1.6(3) . . . . ?
C16 C17 C18 O21 -175.35(18) . . . . ?
C16 C17 C18 C19 2.6(3) . . . . ?
O21 C18 C19 O23 -3.5(3) . . . . ?
C17 C18 C19 O23 178.37(17) . . . . ?
O21 C18 C19 C20 177.43(16) . . . . ?
C17 C18 C19 C20 -0.7(3) . . . . ?
O23 C19 C20 O25 2.6(3) . . . . ?
C18 C19 C20 O25 -178.35(16) . . . . ?
O23 C19 C20 C15 178.67(16) . . . . ?
C18 C19 C20 C15 -2.3(3) . . . . ?
C16 C15 C20 O25 179.39(16) . . . . ?
C14 C15 C20 O25 2.3(2) . . . . ?
C16 C15 C20 C19 3.2(3) . . . . ?
C14 C15 C20 C19 -173.86(16) . . . . ?
C17 C18 O21 C22 -5.8(3) . . . . ?
C19 C18 O21 C22 176.11(17) . . . . ?
C20 C19 O23 C24 -82.4(3) . . . . ?
C18 C19 O23 C24 98.6(3) . . . . ?
C19 C20 O25 C26 -62.5(2) . . . . ?
C15 C20 O25 C26 121.36(19) . . . . ?

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# .RES SHELXL file: job.res
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