# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_kp0695
_database_code_depnum_ccdc_archive 'CCDC 1904463'
loop_
_audit_author_name
_audit_author_address
'Morgane Sanselme'
;University of Rouen
France
;
_audit_update_record             
;
2019-03-20 deposited with the CCDC.	2019-05-24 downloaded from the CCDC.
;

_audit_creation_date             2016-05-10T09:32:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H23 N1 O3 S1'
_chemical_formula_sum            'C22 H23 N O3 S'
_chemical_formula_weight         381.47
_chemical_compound_source        'synthesis as described'

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


_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_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                   9.7914(8)
_cell_length_b                   8.7889(7)
_cell_length_c                   23.7221(19)
_cell_angle_alpha                90
_cell_angle_beta                 99.2680(10)
_cell_angle_gamma                90
_cell_volume                     2014.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3713
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      26.39
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   none

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

_diffrn_measurement_device_type  'SMART APEX I Bruker'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_number            15487
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_full        26.39
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             4105
_reflns_number_gt                3713
_reflns_threshold_expression     >2σ(I)

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

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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 > 2σ(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     
'calc w=1/[σ²(Fo²)+(0.0644P)²+0.8346P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4105
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.149
_refine_ls_wR_factor_gt          0.1454
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_restrained_S_all      1.167
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.049

#----------------------------------------------------------------------------#
#                   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 0 '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 0.006 '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'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3220(2) 1.0965(2) 0.04822(8) 0.0383(4) Uani 1 1 d . . .
C2 C 0.1814(2) 1.0988(3) 0.02680(9) 0.0484(5) Uani 1 1 d . . .
H2 H 0.1286 1.0103 0.0241 0.058 Uiso 1 1 calc R . .
C3 C 0.1232(2) 1.2373(3) 0.00969(11) 0.0547(6) Uani 1 1 d . . .
H3 H 0.0292 1.2419 -0.0048 0.066 Uiso 1 1 calc R . .
C4 C 0.2004(2) 1.3696(3) 0.01339(10) 0.0550(6) Uani 1 1 d . . .
H4 H 0.1579 1.461 0.001 0.066 Uiso 1 1 calc R . .
C5 C 0.3396(2) 1.3675(3) 0.03517(9) 0.0475(5) Uani 1 1 d . . .
H5 H 0.3916 1.4565 0.0377 0.057 Uiso 1 1 calc R . .
C6 C 0.40089(19) 1.2292(2) 0.05331(8) 0.0385(4) Uani 1 1 d . . .
C7 C 0.54048(19) 1.1884(2) 0.07800(8) 0.0389(4) Uani 1 1 d . . .
C8 C 0.6624(2) 1.2927(3) 0.09282(9) 0.0464(5) Uani 1 1 d . . .
H8 H 0.6597 1.365 0.0612 0.056 Uiso 1 1 calc R . .
C9 C 0.7958(2) 1.1992(3) 0.09534(10) 0.0539(6) Uani 1 1 d . . .
H9A H 0.8122 1.1821 0.0566 0.065 Uiso 1 1 calc R . .
H9B H 0.8724 1.2592 0.1147 0.065 Uiso 1 1 calc R . .
C10 C 0.7962(2) 1.0496(3) 0.12457(10) 0.0544(6) Uani 1 1 d . . .
C11 C 0.6708(2) 0.9486(3) 0.11000(10) 0.0523(6) Uani 1 1 d . . .
H11A H 0.6886 0.8728 0.0824 0.063 Uiso 1 1 calc R . .
H11B H 0.6542 0.8957 0.1441 0.063 Uiso 1 1 calc R . .
C12 C 0.54516(19) 1.0376(2) 0.08611(8) 0.0391(4) Uani 1 1 d . . .
C13 C 0.6551(2) 1.3862(3) 0.14721(11) 0.0592(6) Uani 1 1 d . . .
H13 H 0.5641 1.4355 0.1417 0.071 Uiso 1 1 calc R . .
C14 C 0.6642(3) 1.2900(4) 0.20072(12) 0.0784(9) Uani 1 1 d . . .
H14A H 0.7529 1.2408 0.2081 0.118 Uiso 1 1 calc R . .
H14B H 0.5925 1.2144 0.1954 0.118 Uiso 1 1 calc R . .
H14C H 0.653 1.3537 0.2325 0.118 Uiso 1 1 calc R . .
C15 C 0.7629(3) 1.5137(4) 0.15489(17) 0.0921(11) Uani 1 1 d . . .
H15A H 0.7484 1.5773 0.1863 0.138 Uiso 1 1 calc R . .
H15B H 0.754 1.5735 0.1206 0.138 Uiso 1 1 calc R . .
H15C H 0.8539 1.4703 0.1626 0.138 Uiso 1 1 calc R . .
C16 C 0.3331(2) 0.8108(3) 0.15353(9) 0.0473(5) Uani 1 1 d . . .
C17 C 0.2090(3) 0.8659(4) 0.16472(12) 0.0797(9) Uani 1 1 d . . .
H17 H 0.1412 0.8982 0.1351 0.096 Uiso 1 1 calc R . .
C18 C 0.1868(3) 0.8724(5) 0.22047(14) 0.1017(13) Uani 1 1 d . . .
H18 H 0.1025 0.9092 0.228 0.122 Uiso 1 1 calc R . .
C19 C 0.2843(3) 0.8269(5) 0.26517(12) 0.0858(10) Uani 1 1 d . . .
C20 C 0.4060(3) 0.7678(4) 0.25232(12) 0.0828(10) Uani 1 1 d . . .
H20 H 0.4726 0.7324 0.2818 0.099 Uiso 1 1 calc R . .
C21 C 0.4316(2) 0.7595(3) 0.19742(11) 0.0648(7) Uani 1 1 d . . .
H21 H 0.5148 0.7197 0.1898 0.078 Uiso 1 1 calc R . .
C22 C 0.2577(5) 0.8360(7) 0.32621(16) 0.145(2) Uani 1 1 d . . .
H22A H 0.1647 0.8703 0.3265 0.218 Uiso 1 1 calc R . .
H22B H 0.3216 0.9062 0.3473 0.218 Uiso 1 1 calc R . .
H22C H 0.2698 0.7372 0.3435 0.218 Uiso 1 1 calc R . .
N1 N 0.41263(17) 0.97479(19) 0.06695(7) 0.0412(4) Uani 1 1 d . . .
O1 O 0.47980(18) 0.70533(18) 0.08135(8) 0.0578(4) Uani 1 1 d . . .
O2 O 0.23703(17) 0.77233(19) 0.04629(7) 0.0582(4) Uani 1 1 d . . .
O3 O 0.89449(19) 1.0037(3) 0.15709(10) 0.0904(7) Uani 1 1 d . . .
S1 S 0.36404(5) 0.80089(6) 0.08306(2) 0.04412(18) Uani 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C2 1.389(3) . ?
C1 C6 1.393(3) . ?
C1 N1 1.415(2) . ?
C2 C3 1.377(3) . ?
C2 H2 0.93 . ?
C3 C4 1.382(3) . ?
C3 H3 0.93 . ?
C4 C5 1.378(3) . ?
C4 H4 0.93 . ?
C5 C6 1.392(3) . ?
C5 H5 0.93 . ?
C6 C7 1.443(3) . ?
C7 C12 1.339(3) . ?
C7 C8 1.501(3) . ?
C8 C9 1.536(3) . ?
C8 C13 1.541(3) . ?
C8 H8 0.98 . ?
C9 C10 1.487(4) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 O3 1.202(3) . ?
C10 C11 1.510(3) . ?
C11 C12 1.490(3) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 N1 1.416(2) . ?
C13 C14 1.516(4) . ?
C13 C15 1.529(4) . ?
C13 H13 0.98 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?
C16 C17 1.372(3) . ?
C16 C21 1.377(3) . ?
C16 S1 1.749(2) . ?
C17 C18 1.376(4) . ?
C17 H17 0.93 . ?
C18 C19 1.367(4) . ?
C18 H18 0.93 . ?
C19 C20 1.379(4) . ?
C19 C22 1.514(4) . ?
C20 C21 1.367(4) . ?
C20 H20 0.93 . ?
C21 H21 0.93 . ?
C22 H22A 0.96 . ?
C22 H22B 0.96 . ?
C22 H22C 0.96 . ?
N1 S1 1.6633(17) . ?
O1 S1 1.4166(17) . ?
O2 S1 1.4216(16) . ?

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 C1 C6 121.52(19) . . ?
C2 C1 N1 131.32(19) . . ?
C6 C1 N1 107.15(16) . . ?
C3 C2 C1 117.3(2) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.9(2) . . ?
C2 C3 H3 119 . . ?
C4 C3 H3 119 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 118.6(2) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 119.90(18) . . ?
C5 C6 C7 132.46(19) . . ?
C1 C6 C7 107.64(17) . . ?
C12 C7 C6 108.21(17) . . ?
C12 C7 C8 124.29(18) . . ?
C6 C7 C8 127.50(19) . . ?
C7 C8 C9 108.78(18) . . ?
C7 C8 C13 112.31(18) . . ?
C9 C8 C13 113.96(17) . . ?
C7 C8 H8 107.1 . . ?
C9 C8 H8 107.1 . . ?
C13 C8 H8 107.1 . . ?
C10 C9 C8 115.43(18) . . ?
C10 C9 H9A 108.4 . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9B 108.4 . . ?
C8 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
O3 C10 C9 122.5(2) . . ?
O3 C10 C11 119.2(2) . . ?
C9 C10 C11 118.21(19) . . ?
C12 C11 C10 111.7(2) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C7 C12 N1 109.34(17) . . ?
C7 C12 C11 125.53(19) . . ?
N1 C12 C11 125.11(19) . . ?
C14 C13 C15 111.3(2) . . ?
C14 C13 C8 113.5(2) . . ?
C15 C13 C8 111.5(2) . . ?
C14 C13 H13 106.7 . . ?
C15 C13 H13 106.7 . . ?
C8 C13 H13 106.7 . . ?
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 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 120.2(2) . . ?
C17 C16 S1 119.85(18) . . ?
C21 C16 S1 119.89(18) . . ?
C16 C17 C18 118.9(2) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C19 C18 C17 122.3(3) . . ?
C19 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C18 C19 C20 117.3(3) . . ?
C18 C19 C22 121.3(3) . . ?
C20 C19 C22 121.3(3) . . ?
C21 C20 C19 121.9(2) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 C21 C16 119.3(2) . . ?
C20 C21 H21 120.4 . . ?
C16 C21 H21 120.4 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1 N1 C12 107.58(16) . . ?
C1 N1 S1 125.37(14) . . ?
C12 N1 S1 124.44(14) . . ?
O1 S1 O2 120.18(11) . . ?
O1 S1 N1 106.17(9) . . ?
O2 S1 N1 106.00(9) . . ?
O1 S1 C16 108.65(10) . . ?
O2 S1 C16 109.03(11) . . ?
N1 S1 C16 105.89(10) . . ?

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 1.2(3) . . . . ?
N1 C1 C2 C3 -177.2(2) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C4 C5 C6 C7 -179.5(2) . . . . ?
C2 C1 C6 C5 -1.9(3) . . . . ?
N1 C1 C6 C5 176.87(18) . . . . ?
C2 C1 C6 C7 178.63(19) . . . . ?
N1 C1 C6 C7 -2.6(2) . . . . ?
C5 C6 C7 C12 -178.1(2) . . . . ?
C1 C6 C7 C12 1.3(2) . . . . ?
C5 C6 C7 C8 1.9(4) . . . . ?
C1 C6 C7 C8 -178.66(19) . . . . ?
C12 C7 C8 C9 22.0(3) . . . . ?
C6 C7 C8 C9 -158.09(19) . . . . ?
C12 C7 C8 C13 -105.1(2) . . . . ?
C6 C7 C8 C13 74.8(3) . . . . ?
C7 C8 C9 C10 -42.8(3) . . . . ?
C13 C8 C9 C10 83.3(3) . . . . ?
C8 C9 C10 O3 -137.5(3) . . . . ?
C8 C9 C10 C11 46.0(3) . . . . ?
O3 C10 C11 C12 160.9(2) . . . . ?
C9 C10 C11 C12 -22.5(3) . . . . ?
C6 C7 C12 N1 0.6(2) . . . . ?
C8 C7 C12 N1 -179.43(18) . . . . ?
C6 C7 C12 C11 179.07(19) . . . . ?
C8 C7 C12 C11 -1.0(3) . . . . ?
C10 C11 C12 C7 0.0(3) . . . . ?
C10 C11 C12 N1 178.17(19) . . . . ?
C7 C8 C13 C14 65.0(3) . . . . ?
C9 C8 C13 C14 -59.3(3) . . . . ?
C7 C8 C13 C15 -168.4(2) . . . . ?
C9 C8 C13 C15 67.3(3) . . . . ?
C21 C16 C17 C18 1.7(5) . . . . ?
S1 C16 C17 C18 179.9(3) . . . . ?
C16 C17 C18 C19 0.4(6) . . . . ?
C17 C18 C19 C20 -2.4(7) . . . . ?
C17 C18 C19 C22 179.7(5) . . . . ?
C18 C19 C20 C21 2.4(6) . . . . ?
C22 C19 C20 C21 -179.7(4) . . . . ?
C19 C20 C21 C16 -0.4(5) . . . . ?
C17 C16 C21 C20 -1.7(4) . . . . ?
S1 C16 C21 C20 -179.9(2) . . . . ?
C2 C1 N1 C12 -178.4(2) . . . . ?
C6 C1 N1 C12 3.0(2) . . . . ?
C2 C1 N1 S1 -16.2(3) . . . . ?
C6 C1 N1 S1 165.27(14) . . . . ?
C7 C12 N1 C1 -2.3(2) . . . . ?
C11 C12 N1 C1 179.27(19) . . . . ?
C7 C12 N1 S1 -164.74(15) . . . . ?
C11 C12 N1 S1 16.8(3) . . . . ?
C1 N1 S1 O1 161.39(16) . . . . ?
C12 N1 S1 O1 -39.24(19) . . . . ?
C1 N1 S1 O2 32.52(19) . . . . ?
C12 N1 S1 O2 -168.11(16) . . . . ?
C1 N1 S1 C16 -83.22(17) . . . . ?
C12 N1 S1 C16 76.15(18) . . . . ?
C17 C16 S1 O1 -164.7(2) . . . . ?
C21 C16 S1 O1 13.6(2) . . . . ?
C17 C16 S1 O2 -32.0(3) . . . . ?
C21 C16 S1 O2 146.2(2) . . . . ?
C17 C16 S1 N1 81.7(2) . . . . ?
C21 C16 S1 N1 -100.1(2) . . . . ?

# END of CIF
####################################################################### 
# 
# 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_kp0711
_database_code_depnum_ccdc_archive 'CCDC 1904466'
loop_
_audit_author_name
_audit_author_address
'Morgane Sanselme'
;University of Rouen
France
;
_audit_update_record             
;
2019-03-20 deposited with the CCDC.	2019-05-24 downloaded from the CCDC.
;

_audit_creation_date             2016-05-26T09:52:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H20 N2 O5 S1'
_chemical_formula_sum            'C21 H20 N2 O5 S'
_chemical_formula_weight         412.45
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C c'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_Int_Tables_number      9

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

_cell_length_a                   13.6756(13)
_cell_length_b                   15.9188(15)
_cell_length_c                   8.9377(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.551(2)
_cell_angle_gamma                90
_cell_volume                     1912.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3708
_cell_measurement_theta_min      1.98
_cell_measurement_theta_max      26.38
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   none

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

_diffrn_measurement_device_type  'SMART APEX I Bruker'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_number            7525
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_full        26.38
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             3789
_reflns_number_gt                3708
_reflns_threshold_expression     >2σ(I)

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

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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 > 2σ(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     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3789
_refine_ls_number_parameters     263
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.1028
_refine_ls_goodness_of_fit_ref   0.888
_refine_ls_restrained_S_all      0.887
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(6)
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.2
_refine_diff_density_rms         0.051

#----------------------------------------------------------------------------#
#                   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 0 '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 0.006 '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'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.73354(13) 0.69907(11) 0.8877(2) 0.0361(4) Uani 1 1 d . . .
C2 C 0.81524(15) 0.64652(14) 0.9011(3) 0.0473(5) Uani 1 1 d . . .
H2 H 0.8561 0.6464 0.8286 0.057 Uiso 1 1 calc R . .
C3 C 0.83395(16) 0.59396(13) 1.0273(3) 0.0541(5) Uani 1 1 d . . .
H3 H 0.8883 0.5579 1.0384 0.065 Uiso 1 1 calc R . .
C4 C 0.77462(18) 0.59357(13) 1.1366(3) 0.0532(5) Uani 1 1 d . . .
H4 H 0.7904 0.5589 1.2213 0.064 Uiso 1 1 calc R . .
C5 C 0.69122(17) 0.64514(12) 1.1198(2) 0.0454(4) Uani 1 1 d . . .
H5 H 0.6503 0.6449 1.1922 0.054 Uiso 1 1 calc R . .
C6 C 0.67008(14) 0.69688(11) 0.9932(2) 0.0354(4) Uani 1 1 d . . .
C7 C 0.58719(13) 0.75868(10) 0.9510(2) 0.0327(4) Uani 1 1 d . . .
C8 C 0.57114(16) 0.82018(12) 1.0772(2) 0.0416(4) Uani 1 1 d . . .
H8 H 0.5469 0.7901 1.1589 0.05 Uiso 1 1 calc R . .
C9 C 0.49658(16) 0.88736(12) 1.0088(2) 0.0456(5) Uani 1 1 d . . .
H9A H 0.4342 0.8611 0.9633 0.055 Uiso 1 1 calc R . .
H9B H 0.4839 0.9252 1.0882 0.055 Uiso 1 1 calc R . .
C10 C 0.53757(15) 0.93592(11) 0.8899(2) 0.0390(4) Uani 1 1 d . . .
C11 C 0.63435(14) 0.89994(11) 0.8586(2) 0.0379(4) Uani 1 1 d . . .
H11 H 0.6573 0.9308 0.7766 0.045 Uiso 1 1 calc R . .
C12 C 0.61401(12) 0.80712(10) 0.81495(18) 0.0313(3) Uani 1 1 d . . .
H12 H 0.5592 0.8032 0.7276 0.038 Uiso 1 1 calc R . .
C13 C 0.70993(16) 0.90656(14) 1.0082(3) 0.0500(5) Uani 1 1 d . . .
H13A H 0.7234 0.9653 1.033 0.06 Uiso 1 1 calc R . .
H13B H 0.7719 0.8802 0.9959 0.06 Uiso 1 1 calc R . .
C14 C 0.66990(19) 0.86359(14) 1.1392(2) 0.0513(5) Uani 1 1 d . . .
H14A H 0.7177 0.8226 1.1881 0.062 Uiso 1 1 calc R . .
H14B H 0.6603 0.9051 1.2146 0.062 Uiso 1 1 calc R . .
C15 C 0.62470(14) 0.68532(13) 0.5108(2) 0.0391(4) Uani 1 1 d . . .
C16 C 0.64829(17) 0.60081(14) 0.5096(3) 0.0509(5) Uani 1 1 d . . .
H16 H 0.7101 0.5816 0.5589 0.061 Uiso 1 1 calc R . .
C17 C 0.5789(2) 0.54587(15) 0.4344(3) 0.0605(6) Uani 1 1 d . . .
H17 H 0.5942 0.489 0.4338 0.073 Uiso 1 1 calc R . .
C18 C 0.48554(16) 0.57336(15) 0.3584(3) 0.0520(5) Uani 1 1 d . . .
C19 C 0.46463(17) 0.65819(16) 0.3648(3) 0.0520(5) Uani 1 1 d . . .
H19 H 0.4027 0.6778 0.3171 0.062 Uiso 1 1 calc R . .
C20 C 0.53305(16) 0.71446(15) 0.4399(2) 0.0465(4) Uani 1 1 d . . .
H20 H 0.5176 0.7713 0.4427 0.056 Uiso 1 1 calc R . .
C21 C 0.4114(3) 0.5150(2) 0.2691(4) 0.0790(9) Uani 1 1 d . . .
H21A H 0.3746 0.4872 0.3364 0.119 Uiso 1 1 calc R . .
H21B H 0.4455 0.4739 0.219 0.119 Uiso 1 1 calc R . .
H21C H 0.3666 0.5463 0.1943 0.119 Uiso 1 1 calc R . .
N1 N 0.48962(12) 0.70877(11) 0.9037(2) 0.0444(4) Uani 1 1 d . . .
N2 N 0.70353(12) 0.76423(9) 0.77919(18) 0.0359(3) Uani 1 1 d . . .
O1 O 0.49794(14) 0.99772(10) 0.8280(2) 0.0588(4) Uani 1 1 d . . .
O2 O 0.43704(16) 0.72166(18) 0.7807(3) 0.0848(7) Uani 1 1 d . . .
O3 O 0.46926(14) 0.65883(11) 0.9956(2) 0.0650(5) Uani 1 1 d . . .
O4 O 0.68811(14) 0.83881(11) 0.53734(19) 0.0561(4) Uani 1 1 d . . .
O5 O 0.81054(12) 0.72295(13) 0.59760(19) 0.0559(4) Uani 1 1 d . . .
S1 S 0.71437(4) 0.75762(3) 0.59829(5) 0.03966(13) Uani 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C2 1.383(3) . ?
C1 C6 1.394(3) . ?
C1 N2 1.428(2) . ?
C2 C3 1.389(4) . ?
C2 H2 0.93 . ?
C3 C4 1.380(4) . ?
C3 H3 0.93 . ?
C4 C5 1.391(3) . ?
C4 H4 0.93 . ?
C5 C6 1.386(3) . ?
C5 H5 0.93 . ?
C6 C7 1.496(2) . ?
C7 C12 1.540(2) . ?
C7 C8 1.540(3) . ?
C7 N1 1.544(2) . ?
C8 C9 1.526(3) . ?
C8 C14 1.528(3) . ?
C8 H8 0.98 . ?
C9 C10 1.503(3) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 O1 1.207(2) . ?
C10 C11 1.515(3) . ?
C11 C13 1.537(3) . ?
C11 C12 1.540(2) . ?
C11 H11 0.98 . ?
C12 N2 1.487(2) . ?
C12 H12 0.98 . ?
C13 C14 1.540(4) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C15 C20 1.377(3) . ?
C15 C16 1.384(3) . ?
C15 S1 1.758(2) . ?
C16 C17 1.373(3) . ?
C16 H16 0.93 . ?
C17 C18 1.402(3) . ?
C17 H17 0.93 . ?
C18 C19 1.384(4) . ?
C18 C21 1.494(3) . ?
C19 C20 1.378(3) . ?
C19 H19 0.93 . ?
C20 H20 0.93 . ?
C21 H21A 0.96 . ?
C21 H21B 0.96 . ?
C21 H21C 0.96 . ?
N1 O3 1.211(3) . ?
N1 O2 1.216(3) . ?
N2 S1 1.6538(16) . ?
O4 S1 1.4228(18) . ?
O5 S1 1.4273(18) . ?

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 C1 C6 121.26(18) . . ?
C2 C1 N2 128.72(19) . . ?
C6 C1 N2 109.90(15) . . ?
C1 C2 C3 117.4(2) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C4 C3 C2 122.17(18) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 118.9(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 120.28(17) . . ?
C5 C6 C7 129.18(18) . . ?
C1 C6 C7 110.46(16) . . ?
C6 C7 C12 104.45(15) . . ?
C6 C7 C8 115.86(16) . . ?
C12 C7 C8 110.30(14) . . ?
C6 C7 N1 107.91(14) . . ?
C12 C7 N1 111.15(15) . . ?
C8 C7 N1 107.19(15) . . ?
C9 C8 C14 108.04(17) . . ?
C9 C8 C7 109.04(16) . . ?
C14 C8 C7 108.54(16) . . ?
C9 C8 H8 110.4 . . ?
C14 C8 H8 110.4 . . ?
C7 C8 H8 110.4 . . ?
C10 C9 C8 109.61(16) . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
O1 C10 C9 123.27(18) . . ?
O1 C10 C11 123.91(18) . . ?
C9 C10 C11 112.80(15) . . ?
C10 C11 C13 106.53(16) . . ?
C10 C11 C12 106.63(14) . . ?
C13 C11 C12 110.34(15) . . ?
C10 C11 H11 111.1 . . ?
C13 C11 H11 111.1 . . ?
C12 C11 H11 111.1 . . ?
N2 C12 C7 105.33(13) . . ?
N2 C12 C11 112.16(14) . . ?
C7 C12 C11 109.80(14) . . ?
N2 C12 H12 109.8 . . ?
C7 C12 H12 109.8 . . ?
C11 C12 H12 109.8 . . ?
C11 C13 C14 110.80(18) . . ?
C11 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C8 C14 C13 109.82(17) . . ?
C8 C14 H14A 109.7 . . ?
C13 C14 H14A 109.7 . . ?
C8 C14 H14B 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C20 C15 C16 121.2(2) . . ?
C20 C15 S1 119.09(17) . . ?
C16 C15 S1 119.69(15) . . ?
C17 C16 C15 118.81(19) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 121.7(2) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C19 C18 C17 117.5(2) . . ?
C19 C18 C21 120.3(2) . . ?
C17 C18 C21 122.2(2) . . ?
C20 C19 C18 121.8(2) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C15 C20 C19 119.0(2) . . ?
C15 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O3 N1 O2 123.53(19) . . ?
O3 N1 C7 116.55(18) . . ?
O2 N1 C7 119.92(18) . . ?
C1 N2 C12 109.46(15) . . ?
C1 N2 S1 123.48(12) . . ?
C12 N2 S1 117.66(12) . . ?
O4 S1 O5 121.19(11) . . ?
O4 S1 N2 104.77(9) . . ?
O5 S1 N2 106.05(9) . . ?
O4 S1 C15 108.53(10) . . ?
O5 S1 C15 108.25(10) . . ?
N2 S1 C15 107.26(9) . . ?

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 -2.6(3) . . . . ?
N2 C1 C2 C3 173.17(17) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 2.0(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 -2.2(3) . . . . ?
C4 C5 C6 C7 -178.59(18) . . . . ?
C2 C1 C6 C5 3.9(3) . . . . ?
N2 C1 C6 C5 -172.55(16) . . . . ?
C2 C1 C6 C7 -179.05(17) . . . . ?
N2 C1 C6 C7 4.46(19) . . . . ?
C5 C6 C7 C12 170.34(18) . . . . ?
C1 C6 C7 C12 -6.33(19) . . . . ?
C5 C6 C7 C8 48.8(3) . . . . ?
C1 C6 C7 C8 -127.87(17) . . . . ?
C5 C6 C7 N1 -71.3(2) . . . . ?
C1 C6 C7 N1 112.02(16) . . . . ?
C6 C7 C8 C9 170.64(16) . . . . ?
C12 C7 C8 C9 52.3(2) . . . . ?
N1 C7 C8 C9 -68.85(19) . . . . ?
C6 C7 C8 C14 53.2(2) . . . . ?
C12 C7 C8 C14 -65.2(2) . . . . ?
N1 C7 C8 C14 173.68(15) . . . . ?
C14 C8 C9 C10 56.1(2) . . . . ?
C7 C8 C9 C10 -61.7(2) . . . . ?
C8 C9 C10 O1 -172.8(2) . . . . ?
C8 C9 C10 C11 6.1(2) . . . . ?
O1 C10 C11 C13 116.7(2) . . . . ?
C9 C10 C11 C13 -62.2(2) . . . . ?
O1 C10 C11 C12 -125.4(2) . . . . ?
C9 C10 C11 C12 55.6(2) . . . . ?
C6 C7 C12 N2 5.69(17) . . . . ?
C8 C7 C12 N2 130.83(15) . . . . ?
N1 C7 C12 N2 -110.43(15) . . . . ?
C6 C7 C12 C11 -115.27(15) . . . . ?
C8 C7 C12 C11 9.9(2) . . . . ?
N1 C7 C12 C11 128.61(15) . . . . ?
C10 C11 C12 N2 179.30(14) . . . . ?
C13 C11 C12 N2 -65.4(2) . . . . ?
C10 C11 C12 C7 -63.95(18) . . . . ?
C13 C11 C12 C7 51.3(2) . . . . ?
C10 C11 C13 C14 54.7(2) . . . . ?
C12 C11 C13 C14 -60.6(2) . . . . ?
C9 C8 C14 C13 -62.2(2) . . . . ?
C7 C8 C14 C13 55.9(2) . . . . ?
C11 C13 C14 C8 5.3(2) . . . . ?
C20 C15 C16 C17 0.9(4) . . . . ?
S1 C15 C16 C17 -176.9(2) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C16 C17 C18 C19 -1.5(4) . . . . ?
C16 C17 C18 C21 176.6(3) . . . . ?
C17 C18 C19 C20 1.4(4) . . . . ?
C21 C18 C19 C20 -176.8(3) . . . . ?
C16 C15 C20 C19 -1.0(3) . . . . ?
S1 C15 C20 C19 176.78(16) . . . . ?
C18 C19 C20 C15 -0.1(4) . . . . ?
C6 C7 N1 O3 55.5(2) . . . . ?
C12 C7 N1 O3 169.45(17) . . . . ?
C8 C7 N1 O3 -70.0(2) . . . . ?
C6 C7 N1 O2 -125.7(2) . . . . ?
C12 C7 N1 O2 -11.7(3) . . . . ?
C8 C7 N1 O2 108.9(2) . . . . ?
C2 C1 N2 C12 -176.70(18) . . . . ?
C6 C1 N2 C12 -0.55(18) . . . . ?
C2 C1 N2 S1 37.8(3) . . . . ?
C6 C1 N2 S1 -146.03(14) . . . . ?
C7 C12 N2 C1 -3.37(18) . . . . ?
C11 C12 N2 C1 116.03(16) . . . . ?
C7 C12 N2 S1 144.37(13) . . . . ?
C11 C12 N2 S1 -96.23(16) . . . . ?
C1 N2 S1 O4 -172.83(15) . . . . ?
C12 N2 S1 O4 44.27(15) . . . . ?
C1 N2 S1 O5 -43.55(17) . . . . ?
C12 N2 S1 O5 173.55(14) . . . . ?
C1 N2 S1 C15 71.96(17) . . . . ?
C12 N2 S1 C15 -70.94(14) . . . . ?
C20 C15 S1 O4 -19.47(19) . . . . ?
C16 C15 S1 O4 158.35(18) . . . . ?
C20 C15 S1 O5 -152.75(17) . . . . ?
C16 C15 S1 O5 25.1(2) . . . . ?
C20 C15 S1 N2 93.22(18) . . . . ?
C16 C15 S1 N2 -88.96(19) . . . . ?

# END of CIF
####################################################################### 
# 
# 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_struct
_database_code_depnum_ccdc_archive 'CCDC 1904465'
loop_
_audit_author_name
_audit_author_address
'Morgane Sanselme'
;University of Rouen
France
;
_audit_update_record             
;
2019-03-20 deposited with the CCDC.	2019-05-24 downloaded from the CCDC.
;

_audit_creation_date             2017-11-21T14:50:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H19 N3 O8 S1'
_chemical_formula_sum            'C20 H19 N3 O8 S1'
_chemical_formula_weight         461.44
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/a'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   14.4218(11)
_cell_length_b                   10.7034(8)
_cell_length_c                   15.0974(11)
_cell_angle_alpha                90
_cell_angle_beta                 118.2570(13)
_cell_angle_gamma                90
_cell_volume                     2052.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_measurement_reflns_used    3198
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      26.41
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_type   none

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

_diffrn_measurement_device_type  'SMART APEX I Bruker'
_diffrn_ambient_temperature      293
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_number            11645
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_full        26.41
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             4204
_reflns_number_gt                3198
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       SMART
_computing_cell_refinement       SMART
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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 > 2σ(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     
'calc w=1/[σ²(Fo²)+(0.0728P)²+0.3834P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4204
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1411
_refine_ls_wR_factor_gt          0.1286
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.046

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

loop_
_atom_type_symbol
_atom_type_number_in_cell
C 80
H 76
N 12
O 32
S 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.50367(16) 0.1172(2) 0.27415(16) 0.0418(5) Uani 1 1 d . . .
H1 H 0.451 0.1608 0.2144 0.05 Uiso 1 1 calc R . .
C2 C 0.59298(18) 0.2072(2) 0.33784(18) 0.0517(6) Uani 1 1 d . . .
H2A H 0.6108 0.2562 0.294 0.062 Uiso 1 1 calc R . .
H2B H 0.5691 0.2642 0.3727 0.062 Uiso 1 1 calc R . .
C3 C 0.68960(18) 0.1400(2) 0.41356(18) 0.0505(6) Uani 1 1 d . . .
C4 C 0.72679(17) 0.0353(2) 0.37186(18) 0.0525(6) Uani 1 1 d . . .
H4A H 0.7312 -0.0407 0.4087 0.063 Uiso 1 1 calc R . .
H4B H 0.797 0.0546 0.3823 0.063 Uiso 1 1 calc R . .
C5 C 0.65517(17) 0.0125(2) 0.26057(17) 0.0479(5) Uani 1 1 d . . .
H5 H 0.6591 0.085 0.2228 0.057 Uiso 1 1 calc R . .
C6 C 0.54128(15) -0.00176(19) 0.24146(15) 0.0398(5) Uani 1 1 d . . .
C7 C 0.52190(15) -0.10560(19) 0.29694(14) 0.0368(4) Uani 1 1 d . . .
C8 C 0.54838(15) -0.2307(2) 0.30243(15) 0.0423(5) Uani 1 1 d . . .
H8 H 0.5829 -0.2621 0.2685 0.051 Uiso 1 1 calc R . .
C9 C 0.52135(16) -0.3066(2) 0.36029(15) 0.0424(5) Uani 1 1 d . . .
C10 C 0.47047(17) -0.2639(2) 0.41175(16) 0.0481(5) Uani 1 1 d . . .
H10 H 0.4536 -0.3188 0.4497 0.058 Uiso 1 1 calc R . .
C11 C 0.44464(17) -0.1394(2) 0.40678(16) 0.0470(5) Uani 1 1 d . . .
H11 H 0.4108 -0.1086 0.4416 0.056 Uiso 1 1 calc R . .
C12 C 0.47038(15) -0.0609(2) 0.34859(14) 0.0377(4) Uani 1 1 d . . .
C13 C 0.24872(16) 0.0662(2) 0.19287(17) 0.0469(5) Uani 1 1 d . . .
C14 C 0.21182(17) -0.0543(2) 0.19003(18) 0.0531(6) Uani 1 1 d . . .
H14 H 0.229 -0.0971 0.2494 0.064 Uiso 1 1 calc R . .
C15 C 0.14959(19) -0.1097(3) 0.0985(2) 0.0608(7) Uani 1 1 d . . .
H15 H 0.1251 -0.1905 0.0966 0.073 Uiso 1 1 calc R . .
C16 C 0.12277(18) -0.0475(3) 0.00928(19) 0.0577(6) Uani 1 1 d . . .
C17 C 0.1574(2) 0.0741(3) 0.0138(2) 0.0635(7) Uani 1 1 d . . .
H17 H 0.138 0.118 -0.0456 0.076 Uiso 1 1 calc R . .
C18 C 0.22030(19) 0.1315(2) 0.10482(19) 0.0586(6) Uani 1 1 d . . .
H18 H 0.2432 0.2132 0.1068 0.07 Uiso 1 1 calc R . .
C19 C 0.0567(2) -0.1109(3) -0.0907(2) 0.0818(9) Uani 1 1 d . . .
H19A H 0.1002 -0.1315 -0.1209 0.123 Uiso 1 1 calc R . .
H19B H 0.0015 -0.0556 -0.1343 0.123 Uiso 1 1 calc R . .
H19C H 0.0265 -0.1858 -0.0804 0.123 Uiso 1 1 calc R . .
C20 C 0.7529(2) -0.0693(3) 0.1857(2) 0.0744(8) Uani 1 1 d . . .
H20A H 0.7189 -0.0158 0.128 0.112 Uiso 1 1 calc R . .
H20B H 0.7726 -0.1462 0.1664 0.112 Uiso 1 1 calc R . .
H20C H 0.8148 -0.0286 0.2361 0.112 Uiso 1 1 calc R . .
N1 N 0.45349(12) 0.07004(17) 0.33416(12) 0.0412(4) Uani 1 1 d . . .
N2 N 0.47243(16) -0.0196(2) 0.12681(14) 0.0543(5) Uani 1 1 d . . .
N3 N 0.54605(16) -0.44026(19) 0.36446(15) 0.0535(5) Uani 1 1 d . . .
O1 O 0.34727(13) 0.26153(17) 0.29495(14) 0.0693(5) Uani 1 1 d . . .
O2 O 0.31395(13) 0.08858(19) 0.38505(13) 0.0675(5) Uani 1 1 d . . .
O3 O 0.46836(19) 0.0697(2) 0.07455(14) 0.0849(6) Uani 1 1 d . . .
O4 O 0.4284(2) -0.1163(2) 0.09478(14) 0.0983(8) Uani 1 1 d . . .
O5 O 0.58094(18) -0.47920(17) 0.31045(16) 0.0794(6) Uani 1 1 d . . .
O6 O 0.52980(19) -0.50657(18) 0.42069(17) 0.0854(6) Uani 1 1 d . . .
O7 O 0.68257(14) -0.09477(17) 0.22505(15) 0.0665(5) Uani 1 1 d . . .
O8 O 0.73443(15) 0.1696(2) 0.50072(14) 0.0775(6) Uani 1 1 d . . .
S1 S 0.33739(4) 0.13152(6) 0.30893(5) 0.0515(2) Uani 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 N1 1.490(2) . ?
C1 C2 1.529(3) . ?
C1 C6 1.553(3) . ?
C1 H1 0.98 . ?
C2 C3 1.502(3) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 O8 1.202(3) . ?
C3 C4 1.503(3) . ?
C4 C5 1.519(3) . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C5 O7 1.401(3) . ?
C5 C6 1.535(3) . ?
C5 H5 0.98 . ?
C6 C7 1.495(3) . ?
C6 N2 1.546(3) . ?
C7 C8 1.384(3) . ?
C7 C12 1.392(3) . ?
C8 C9 1.378(3) . ?
C8 H8 0.93 . ?
C9 C10 1.375(3) . ?
C9 N3 1.468(3) . ?
C10 C11 1.376(3) . ?
C10 H10 0.93 . ?
C11 C12 1.387(3) . ?
C11 H11 0.93 . ?
C12 N1 1.422(3) . ?
C13 C18 1.381(3) . ?
C13 C14 1.388(3) . ?
C13 S1 1.753(2) . ?
C14 C15 1.376(3) . ?
C14 H14 0.93 . ?
C15 C16 1.383(4) . ?
C15 H15 0.93 . ?
C16 C17 1.384(4) . ?
C16 C19 1.512(4) . ?
C17 C18 1.381(4) . ?
C17 H17 0.93 . ?
C18 H18 0.93 . ?
C19 H19A 0.96 . ?
C19 H19B 0.96 . ?
C19 H19C 0.96 . ?
C20 O7 1.424(3) . ?
C20 H20A 0.96 . ?
C20 H20B 0.96 . ?
C20 H20C 0.96 . ?
N1 S1 1.6666(17) . ?
N2 O4 1.190(3) . ?
N2 O3 1.223(3) . ?
N3 O6 1.212(3) . ?
N3 O5 1.217(2) . ?
O1 S1 1.4246(19) . ?
O2 S1 1.4192(18) . ?

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
N1 C1 C2 109.74(17) . . ?
N1 C1 C6 105.00(16) . . ?
C2 C1 C6 113.53(17) . . ?
N1 C1 H1 109.5 . . ?
C2 C1 H1 109.5 . . ?
C6 C1 H1 109.5 . . ?
C3 C2 C1 112.26(19) . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
O8 C3 C2 122.1(2) . . ?
O8 C3 C4 122.8(2) . . ?
C2 C3 C4 115.1(2) . . ?
C3 C4 C5 113.10(19) . . ?
C3 C4 H4A 109 . . ?
C5 C4 H4A 109 . . ?
C3 C4 H4B 109 . . ?
C5 C4 H4B 109 . . ?
H4A C4 H4B 107.8 . . ?
O7 C5 C4 112.8(2) . . ?
O7 C5 C6 108.47(18) . . ?
C4 C5 C6 109.31(17) . . ?
O7 C5 H5 108.7 . . ?
C4 C5 H5 108.7 . . ?
C6 C5 H5 108.7 . . ?
C7 C6 C5 115.85(17) . . ?
C7 C6 N2 110.11(17) . . ?
C5 C6 N2 106.59(16) . . ?
C7 C6 C1 104.20(16) . . ?
C5 C6 C1 111.23(17) . . ?
N2 C6 C1 108.74(16) . . ?
C8 C7 C12 120.27(18) . . ?
C8 C7 C6 129.28(17) . . ?
C12 C7 C6 110.45(18) . . ?
C9 C8 C7 117.13(18) . . ?
C9 C8 H8 121.4 . . ?
C7 C8 H8 121.4 . . ?
C10 C9 C8 123.3(2) . . ?
C10 C9 N3 118.91(19) . . ?
C8 C9 N3 117.80(19) . . ?
C9 C10 C11 119.63(19) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 118.29(19) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
C11 C12 C7 121.4(2) . . ?
C11 C12 N1 128.02(18) . . ?
C7 C12 N1 110.54(17) . . ?
C18 C13 C14 120.4(2) . . ?
C18 C13 S1 120.25(19) . . ?
C14 C13 S1 119.28(18) . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 121.3(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 118.4(2) . . ?
C15 C16 C19 120.6(3) . . ?
C17 C16 C19 120.9(3) . . ?
C18 C17 C16 121.3(2) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C13 C18 C17 119.2(2) . . ?
C13 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O7 C20 H20A 109.5 . . ?
O7 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O7 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C12 N1 C1 109.25(15) . . ?
C12 N1 S1 120.33(13) . . ?
C1 N1 S1 116.87(14) . . ?
O4 N2 O3 124.3(2) . . ?
O4 N2 C6 119.9(2) . . ?
O3 N2 C6 115.8(2) . . ?
O6 N3 O5 123.2(2) . . ?
O6 N3 C9 118.5(2) . . ?
O5 N3 C9 118.29(19) . . ?
C5 O7 C20 112.84(19) . . ?
O2 S1 O1 121.00(11) . . ?
O2 S1 N1 106.60(10) . . ?
O1 S1 N1 105.04(10) . . ?
O2 S1 C13 109.85(11) . . ?
O1 S1 C13 108.56(11) . . ?
N1 S1 C13 104.45(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 76.0(2) . . . . ?
C6 C1 C2 C3 -41.1(3) . . . . ?
C1 C2 C3 O8 -130.5(2) . . . . ?
C1 C2 C3 C4 50.6(3) . . . . ?
O8 C3 C4 C5 178.0(2) . . . . ?
C2 C3 C4 C5 -3.1(3) . . . . ?
C3 C4 C5 O7 -172.39(18) . . . . ?
C3 C4 C5 C6 -51.6(2) . . . . ?
O7 C5 C6 C7 64.2(2) . . . . ?
C4 C5 C6 C7 -59.2(2) . . . . ?
O7 C5 C6 N2 -58.7(2) . . . . ?
C4 C5 C6 N2 177.93(18) . . . . ?
O7 C5 C6 C1 -177.09(17) . . . . ?
C4 C5 C6 C1 59.5(2) . . . . ?
N1 C1 C6 C7 -7.18(19) . . . . ?
C2 C1 C6 C7 112.70(19) . . . . ?
N1 C1 C6 C5 -132.69(17) . . . . ?
C2 C1 C6 C5 -12.8(2) . . . . ?
N1 C1 C6 N2 110.23(17) . . . . ?
C2 C1 C6 N2 -129.89(19) . . . . ?
C5 C6 C7 C8 -51.8(3) . . . . ?
N2 C6 C7 C8 69.2(3) . . . . ?
C1 C6 C7 C8 -174.3(2) . . . . ?
C5 C6 C7 C12 127.71(19) . . . . ?
N2 C6 C7 C12 -111.27(18) . . . . ?
C1 C6 C7 C12 5.2(2) . . . . ?
C12 C7 C8 C9 0.1(3) . . . . ?
C6 C7 C8 C9 179.55(19) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C7 C8 C9 N3 178.21(18) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
N3 C9 C10 C11 -178.55(19) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C11 C12 C7 -0.6(3) . . . . ?
C10 C11 C12 N1 -178.60(19) . . . . ?
C8 C7 C12 C11 0.3(3) . . . . ?
C6 C7 C12 C11 -179.27(18) . . . . ?
C8 C7 C12 N1 178.57(17) . . . . ?
C6 C7 C12 N1 -1.0(2) . . . . ?
C18 C13 C14 C15 2.2(3) . . . . ?
S1 C13 C14 C15 -174.36(18) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C14 C15 C16 C17 -1.9(4) . . . . ?
C14 C15 C16 C19 178.3(2) . . . . ?
C15 C16 C17 C18 2.1(4) . . . . ?
C19 C16 C17 C18 -178.1(2) . . . . ?
C14 C13 C18 C17 -2.0(4) . . . . ?
S1 C13 C18 C17 174.55(18) . . . . ?
C16 C17 C18 C13 -0.2(4) . . . . ?
C11 C12 N1 C1 174.2(2) . . . . ?
C7 C12 N1 C1 -4.0(2) . . . . ?
C11 C12 N1 S1 -46.4(3) . . . . ?
C7 C12 N1 S1 135.39(15) . . . . ?
C2 C1 N1 C12 -115.39(18) . . . . ?
C6 C1 N1 C12 7.0(2) . . . . ?
C2 C1 N1 S1 103.66(17) . . . . ?
C6 C1 N1 S1 -133.97(14) . . . . ?
C7 C6 N2 O4 -12.4(3) . . . . ?
C5 C6 N2 O4 114.0(3) . . . . ?
C1 C6 N2 O4 -126.0(2) . . . . ?
C7 C6 N2 O3 168.3(2) . . . . ?
C5 C6 N2 O3 -65.3(3) . . . . ?
C1 C6 N2 O3 54.7(3) . . . . ?
C10 C9 N3 O6 -6.9(3) . . . . ?
C8 C9 N3 O6 174.7(2) . . . . ?
C10 C9 N3 O5 172.4(2) . . . . ?
C8 C9 N3 O5 -6.0(3) . . . . ?
C4 C5 O7 C20 -92.3(2) . . . . ?
C6 C5 O7 C20 146.4(2) . . . . ?
C12 N1 S1 O2 52.94(17) . . . . ?
C1 N1 S1 O2 -170.62(15) . . . . ?
C12 N1 S1 O1 -177.51(15) . . . . ?
C1 N1 S1 O1 -41.07(17) . . . . ?
C12 N1 S1 C13 -63.33(17) . . . . ?
C1 N1 S1 C13 73.11(17) . . . . ?
C18 C13 S1 O2 148.98(19) . . . . ?
C14 C13 S1 O2 -34.4(2) . . . . ?
C18 C13 S1 O1 14.6(2) . . . . ?
C14 C13 S1 O1 -168.76(18) . . . . ?
C18 C13 S1 N1 -97.0(2) . . . . ?
C14 C13 S1 N1 79.58(19) . . . . ?

# END of CIF
####################################################################### 
# 
# 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_brr221
_database_code_depnum_ccdc_archive 'CCDC 1904469'
loop_
_audit_author_name
_audit_author_address
'Morgane Sanselme'
;University of Rouen
France
;
_audit_update_record             
;
2019-03-20 deposited with the CCDC.	2019-05-24 downloaded from the CCDC.
;

_audit_creation_date             2017-11-22T09:48:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H19 Br1 N2 O6 S1'
_chemical_formula_sum            'C20 H19 Br N2 O6 S'
_chemical_formula_weight         495.34
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/a'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   10.7343(11)
_cell_length_b                   12.8521(13)
_cell_length_c                   15.5222(15)
_cell_angle_alpha                90
_cell_angle_beta                 95.998(2)
_cell_angle_gamma                90
_cell_volume                     2129.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2242
_cell_measurement_theta_min      2.06
_cell_measurement_theta_max      26.42
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    2.068
_exptl_absorpt_correction_type   none

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

_diffrn_measurement_device_type  'SMART APEX I Bruker'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.061
_diffrn_reflns_number            12228
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_full        26.42
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             4346
_reflns_number_gt                2242
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       SMART
_computing_cell_refinement       SMART
_computing_data_reduction        SAINT
_computing_structure_solution    SHELSX-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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 > 2σ(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     
'calc w=1/[σ²(Fo²)+(0.0805P)²+1.1928P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4346
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1325
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_ref         0.1998
_refine_ls_wR_factor_gt          0.1662
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.902
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.065

#----------------------------------------------------------------------------#
#                   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 0 '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'
O O 0.0106 0.006 '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'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0447(4) 0.0025(4) 0.8025(3) 0.0589(13) Uani 1 1 d . . .
C2 C 0.0936(5) -0.0833(5) 0.8483(4) 0.0750(16) Uani 1 1 d . . .
H2 H 0.0944 -0.1486 0.8225 0.09 Uiso 1 1 calc R . .
C3 C 0.1408(5) -0.0685(6) 0.9329(5) 0.0829(18) Uani 1 1 d . . .
H3 H 0.1723 -0.1254 0.9652 0.099 Uiso 1 1 calc R . .
C4 C 0.1431(5) 0.0281(6) 0.9715(4) 0.0800(18) Uani 1 1 d . . .
H4 H 0.1772 0.0365 1.0286 0.096 Uiso 1 1 calc R . .
C5 C 0.0945(5) 0.1118(5) 0.9246(4) 0.0694(15) Uani 1 1 d . . .
C6 C 0.0435(4) 0.0998(4) 0.8394(3) 0.0541(12) Uani 1 1 d . . .
C7 C -0.0156(4) 0.1768(4) 0.7758(3) 0.0561(13) Uani 1 1 d . . .
H7 H 0.0387 0.2374 0.7716 0.067 Uiso 1 1 calc R . .
C8 C -0.0313(5) 0.1160(4) 0.6892(3) 0.0578(13) Uani 1 1 d . . .
H8 H -0.1178 0.1224 0.6623 0.069 Uiso 1 1 calc R . .
C9 C 0.0587(5) 0.1522(4) 0.6262(3) 0.0681(15) Uani 1 1 d . . .
H9A H 0.142 0.1571 0.6567 0.082 Uiso 1 1 calc R . .
H9B H 0.0613 0.1002 0.5811 0.082 Uiso 1 1 calc R . .
C10 C 0.0256(7) 0.2532(5) 0.5854(4) 0.0792(18) Uani 1 1 d . . .
C11 C 0.1294(13) 0.2876(8) 0.5241(5) 0.148(6) Uani 1 1 d . . .
H11 H 0.207 0.2559 0.5226 0.177 Uiso 1 1 calc R . .
C12 C 0.0953(10) 0.3545(12) 0.4841(9) 0.173(5) Uani 1 1 d . . .
H12 H 0.017 0.3821 0.4912 0.208 Uiso 1 1 calc R . .
C13 C 0.2799(8) 0.3473(12) 0.4191(9) 0.213(8) Uani 1 1 d . . .
H13A H 0.1730 0.8611 0.5270 0.32 Uiso 1 1 calc R . .
H13B H 0.1690 0.8640 0.6270 0.32 Uiso 1 1 calc R . .
H13C H 0.2430 0.7750 0.5850 0.32 Uiso 1 1 calc R . .
O4 O 0.1754(11) 0.4053(6) 0.4146(5) 0.198(4) Uani 1 1 d . . .
C14 C -0.2355(5) -0.0809(4) 0.7162(3) 0.0636(14) Uani 1 1 d . . .
C15 C -0.3331(6) -0.0190(5) 0.6800(4) 0.0847(19) Uani 1 1 d . . .
H15 H -0.3271 0.0159 0.6281 0.102 Uiso 1 1 calc R . .
C16 C -0.4394(6) -0.0101(5) 0.7224(5) 0.095(2) Uani 1 1 d . . .
H16 H -0.5047 0.0321 0.6989 0.114 Uiso 1 1 calc R . .
C17 C -0.4512(6) -0.0623(5) 0.7988(5) 0.090(2) Uani 1 1 d . . .
C18 C -0.3539(6) -0.1224(5) 0.8329(4) 0.0788(17) Uani 1 1 d . . .
H18 H -0.3601 -0.1569 0.8849 0.095 Uiso 1 1 calc R . .
C19 C -0.2471(6) -0.1333(4) 0.7927(4) 0.0712(15) Uani 1 1 d . . .
H19 H -0.1826 -0.1758 0.8168 0.085 Uiso 1 1 calc R . .
C20 C -0.5688(7) -0.0527(7) 0.8426(6) 0.140(3) Uani 1 1 d . . .
H20A H -0.6078 -0.1198 0.8447 0.211 Uiso 1 1 calc R . .
H20B H -0.6252 -0.0053 0.8106 0.211 Uiso 1 1 calc R . .
H20C H -0.5486 -0.027 0.9004 0.211 Uiso 1 1 calc R . .
Br1 Br 0.09043(7) 0.24536(5) 0.97508(4) 0.0999(4) Uani 1 1 d . . .
N1 N -0.0049(4) 0.0061(3) 0.7142(3) 0.0595(11) Uani 1 1 d . . .
N2 N -0.1426(5) 0.2091(5) 0.8002(3) 0.0789(14) Uani 1 1 d . . .
O1 O -0.2104(4) 0.1450(5) 0.8225(4) 0.130(2) Uani 1 1 d . . .
O2 O -0.1686(6) 0.2988(5) 0.7957(4) 0.151(2) Uani 1 1 d . . .
O3 O -0.0695(5) 0.2980(4) 0.6030(3) 0.1062(15) Uani 1 1 d . . .
O5 O -0.1202(4) -0.0539(3) 0.5797(2) 0.0944(14) Uani 1 1 d . . .
O6 O -0.0356(4) -0.1817(3) 0.6901(3) 0.0960(13) Uani 1 1 d . . .
S1 S -0.09659(15) -0.08596(12) 0.66781(9) 0.0742(5) Uani 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C6 1.376(7) . ?
C1 C2 1.384(7) . ?
C1 N1 1.419(6) . ?
C2 C3 1.370(8) . ?
C2 H2 0.93 . ?
C3 C4 1.379(8) . ?
C3 H3 0.93 . ?
C4 C5 1.371(8) . ?
C4 H4 0.93 . ?
C5 C6 1.386(7) . ?
C5 Br1 1.889(5) . ?
C6 C7 1.492(7) . ?
C7 N2 1.511(7) . ?
C7 C8 1.549(6) . ?
C7 H7 0.98 . ?
C8 N1 1.485(6) . ?
C8 C9 1.517(7) . ?
C8 H8 0.98 . ?
C9 C10 1.471(8) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 O3 1.228(7) . ?
C10 C11 1.601(14) . ?
C11 C12 1.100(15) . ?
C11 H11 0.93 . ?
C12 O4 1.589(16) . ?
C12 H12 0.93 . ?
C13 O4 1.342(12) . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C14 C19 1.382(7) . ?
C14 C15 1.387(7) . ?
C14 S1 1.740(6) . ?
C15 C16 1.380(9) . ?
C15 H15 0.93 . ?
C16 C17 1.380(9) . ?
C16 H16 0.93 . ?
C17 C18 1.361(8) . ?
C17 C20 1.500(9) . ?
C18 C19 1.367(8) . ?
C18 H18 0.93 . ?
C19 H19 0.93 . ?
C20 H20A 0.96 . ?
C20 H20B 0.96 . ?
C20 H20C 0.96 . ?
N1 S1 1.655(4) . ?
N2 O1 1.174(6) . ?
N2 O2 1.186(7) . ?
O5 S1 1.426(4) . ?
O6 S1 1.419(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.0(5) . . ?
C6 C1 N1 110.7(4) . . ?
C2 C1 N1 127.3(5) . . ?
C3 C2 C1 117.6(6) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 121.9(6) . . ?
C2 C3 H3 119 . . ?
C4 C3 H3 119 . . ?
C5 C4 C3 119.2(6) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 Br1 121.1(5) . . ?
C6 C5 Br1 118.2(5) . . ?
C1 C6 C5 118.6(5) . . ?
C1 C6 C7 110.4(4) . . ?
C5 C6 C7 131.0(5) . . ?
C6 C7 N2 110.4(4) . . ?
C6 C7 C8 103.9(4) . . ?
N2 C7 C8 109.7(4) . . ?
C6 C7 H7 110.9 . . ?
N2 C7 H7 110.9 . . ?
C8 C7 H7 110.9 . . ?
N1 C8 C9 110.1(4) . . ?
N1 C8 C7 104.6(4) . . ?
C9 C8 C7 112.7(4) . . ?
N1 C8 H8 109.8 . . ?
C9 C8 H8 109.8 . . ?
C7 C8 H8 109.8 . . ?
C10 C9 C8 114.0(5) . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.6 . . ?
O3 C10 C9 119.2(6) . . ?
O3 C10 C11 130.4(7) . . ?
C9 C10 C11 110.4(7) . . ?
C12 C11 C10 109.9(16) . . ?
C12 C11 H11 125 . . ?
C10 C11 H11 125 . . ?
C11 C12 O4 122.2(13) . . ?
C11 C12 H12 118.9 . . ?
O4 C12 H12 118.9 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C13 O4 C12 104.2(10) . . ?
C19 C14 C15 119.7(6) . . ?
C19 C14 S1 120.8(5) . . ?
C15 C14 S1 119.5(5) . . ?
C16 C15 C14 118.8(6) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 121.6(6) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C16 118.3(7) . . ?
C18 C17 C20 121.3(7) . . ?
C16 C17 C20 120.4(7) . . ?
C17 C18 C19 121.8(6) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C14 119.8(5) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 N1 C8 109.1(4) . . ?
C1 N1 S1 122.9(4) . . ?
C8 N1 S1 118.5(3) . . ?
O1 N2 O2 123.4(6) . . ?
O1 N2 C7 118.9(5) . . ?
O2 N2 C7 117.7(6) . . ?
O6 S1 O5 121.0(3) . . ?
O6 S1 N1 106.0(3) . . ?
O5 S1 N1 104.4(2) . . ?
O6 S1 C14 108.8(3) . . ?
O5 S1 C14 109.2(3) . . ?
N1 S1 C14 106.4(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
C6 C1 C2 C3 0.4(8) . . . . ?
N1 C1 C2 C3 177.8(5) . . . . ?
C1 C2 C3 C4 -1.6(8) . . . . ?
C2 C3 C4 C5 1.3(9) . . . . ?
C3 C4 C5 C6 0.1(8) . . . . ?
C3 C4 C5 Br1 178.1(4) . . . . ?
C2 C1 C6 C5 0.9(7) . . . . ?
N1 C1 C6 C5 -176.8(4) . . . . ?
C2 C1 C6 C7 -179.4(4) . . . . ?
N1 C1 C6 C7 2.8(6) . . . . ?
C4 C5 C6 C1 -1.2(7) . . . . ?
Br1 C5 C6 C1 -179.2(4) . . . . ?
C4 C5 C6 C7 179.3(5) . . . . ?
Br1 C5 C6 C7 1.2(7) . . . . ?
C1 C6 C7 N2 108.7(5) . . . . ?
C5 C6 C7 N2 -71.7(7) . . . . ?
C1 C6 C7 C8 -8.9(5) . . . . ?
C5 C6 C7 C8 170.7(5) . . . . ?
C6 C7 C8 N1 11.2(5) . . . . ?
N2 C7 C8 N1 -106.8(5) . . . . ?
C6 C7 C8 C9 -108.4(5) . . . . ?
N2 C7 C8 C9 133.6(5) . . . . ?
N1 C8 C9 C10 169.4(4) . . . . ?
C7 C8 C9 C10 -74.2(6) . . . . ?
C8 C9 C10 O3 -1.4(8) . . . . ?
C8 C9 C10 C11 177.0(5) . . . . ?
O3 C10 C11 C12 -13.1(13) . . . . ?
C9 C10 C11 C12 168.7(9) . . . . ?
C10 C11 C12 O4 -178.4(7) . . . . ?
C11 C12 O4 C13 1.2(14) . . . . ?
C19 C14 C15 C16 0.9(8) . . . . ?
S1 C14 C15 C16 -175.5(5) . . . . ?
C14 C15 C16 C17 -0.9(10) . . . . ?
C15 C16 C17 C18 1.0(11) . . . . ?
C15 C16 C17 C20 -178.8(7) . . . . ?
C16 C17 C18 C19 -1.1(10) . . . . ?
C20 C17 C18 C19 178.7(6) . . . . ?
C17 C18 C19 C14 1.2(9) . . . . ?
C15 C14 C19 C18 -1.0(8) . . . . ?
S1 C14 C19 C18 175.4(4) . . . . ?
C6 C1 N1 C8 5.0(5) . . . . ?
C2 C1 N1 C8 -172.6(5) . . . . ?
C6 C1 N1 S1 -140.7(4) . . . . ?
C2 C1 N1 S1 41.7(7) . . . . ?
C9 C8 N1 C1 111.1(4) . . . . ?
C7 C8 N1 C1 -10.2(5) . . . . ?
C9 C8 N1 S1 -101.5(4) . . . . ?
C7 C8 N1 S1 137.2(3) . . . . ?
C6 C7 N2 O1 -43.6(7) . . . . ?
C8 C7 N2 O1 70.4(7) . . . . ?
C6 C7 N2 O2 136.5(6) . . . . ?
C8 C7 N2 O2 -109.5(6) . . . . ?
C1 N1 S1 O6 -48.9(4) . . . . ?
C8 N1 S1 O6 168.5(3) . . . . ?
C1 N1 S1 O5 -177.7(4) . . . . ?
C8 N1 S1 O5 39.6(4) . . . . ?
C1 N1 S1 C14 66.8(4) . . . . ?
C8 N1 S1 C14 -75.9(4) . . . . ?
C19 C14 S1 O6 28.5(5) . . . . ?
C15 C14 S1 O6 -155.1(4) . . . . ?
C19 C14 S1 O5 162.5(4) . . . . ?
C15 C14 S1 O5 -21.1(5) . . . . ?
C19 C14 S1 N1 -85.3(5) . . . . ?
C15 C14 S1 N1 91.2(5) . . . . ?

# END of CIF
####################################################################### 
# 
# 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_kp0709
_database_code_depnum_ccdc_archive 'CCDC 1904464'
loop_
_audit_author_name
_audit_author_address
'Morgane Sanselme'
;University of Rouen
France
;
_audit_update_record             
;
2019-03-20 deposited with the CCDC.	2019-05-24 downloaded from the CCDC.
;

_audit_creation_date             2016-06-01T10:27:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H23 N2 O5 S1'
_chemical_formula_sum            'C22 H23 N2 O5 S'
_chemical_formula_weight         427.48
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9731(11)
_cell_length_b                   10.2645(12)
_cell_length_c                   13.9133(17)
_cell_angle_alpha                70.000(2)
_cell_angle_beta                 73.252(2)
_cell_angle_gamma                66.708(2)
_cell_volume                     1088.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3940
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      26.41
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             450
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_type   none

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

_diffrn_measurement_device_type  'SMART APEX I Bruker'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_number            8664
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_full        26.41
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_reflns_number_total             4374
_reflns_number_gt                3940
_reflns_threshold_expression     >2σ(I)

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

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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 > 2σ(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     
'calc w=1/[σ²(Fo²)+(0.0712P)²+0.3152P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4374
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1433
_refine_ls_wR_factor_gt          0.1389
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.041

#----------------------------------------------------------------------------#
#                   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 0 '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 0.006 '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'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0301(2) -0.0096(2) 0.11619(16) 0.0519(5) Uani 1 1 d . . .
C2 C -0.1132(3) -0.0480(2) 0.19124(17) 0.0552(5) Uani 1 1 d . . .
H2A H -0.0872 -0.0874 0.2607 0.066 Uiso 1 1 calc R . .
H2B H -0.1311 -0.1237 0.1737 0.066 Uiso 1 1 calc R . .
C3 C -0.2720(2) 0.08512(19) 0.19033(15) 0.0435(4) Uani 1 1 d . . .
H3 H -0.2855 0.1249 0.1174 0.052 Uiso 1 1 calc R . .
C4 C -0.2488(2) 0.20901(17) 0.21864(12) 0.0365(4) Uani 1 1 d . . .
C5 C -0.3485(2) 0.36441(17) 0.17065(12) 0.0352(3) Uani 1 1 d . . .
C6 C -0.5095(2) 0.4227(2) 0.15529(15) 0.0449(4) Uani 1 1 d . . .
H6 H -0.5739 0.3626 0.1746 0.054 Uiso 1 1 calc R . .
C7 C -0.5741(2) 0.5709(2) 0.11106(16) 0.0519(5) Uani 1 1 d . . .
H7 H -0.6829 0.6113 0.101 0.062 Uiso 1 1 calc R . .
C8 C -0.4788(3) 0.6593(2) 0.08182(16) 0.0561(5) Uani 1 1 d . . .
H8 H -0.5254 0.7596 0.054 0.067 Uiso 1 1 calc R . .
C9 C -0.3160(3) 0.6029(2) 0.09261(16) 0.0540(5) Uani 1 1 d . . .
H9 H -0.2508 0.6628 0.0701 0.065 Uiso 1 1 calc R . .
C10 C -0.2525(2) 0.45439(19) 0.13797(13) 0.0394(4) Uani 1 1 d . . .
C11 C -0.0703(2) 0.21273(19) 0.18424(14) 0.0418(4) Uani 1 1 d . . .
H11 H -0.0109 0.1614 0.2429 0.05 Uiso 1 1 calc R . .
C12 C 0.0228(2) 0.1462(2) 0.09318(16) 0.0502(5) Uani 1 1 d . . .
H12A H -0.0305 0.2045 0.0334 0.06 Uiso 1 1 calc R . .
H12B H 0.1342 0.1497 0.0755 0.06 Uiso 1 1 calc R . .
C13 C -0.4286(3) 0.0429(2) 0.24886(19) 0.0612(6) Uani 1 1 d . . .
H13 H -0.517 0.1327 0.2613 0.073 Uiso 1 1 calc R . .
C14 C -0.4816(4) -0.0120(4) 0.1796(3) 0.0943(9) Uani 1 1 d . . .
H14A H -0.3947 -0.0971 0.1627 0.141 Uiso 1 1 calc R . .
H14B H -0.5044 0.0638 0.1169 0.141 Uiso 1 1 calc R . .
H14C H -0.579 -0.0374 0.2156 0.141 Uiso 1 1 calc R . .
C15 C -0.4134(4) -0.0703(3) 0.3539(2) 0.0891(9) Uani 1 1 d . . .
H15A H -0.5165 -0.0879 0.3845 0.134 Uiso 1 1 calc R . .
H15B H -0.3855 -0.0339 0.399 0.134 Uiso 1 1 calc R . .
H15C H -0.3287 -0.1604 0.3442 0.134 Uiso 1 1 calc R . .
C16 C -0.0562(3) 0.4089(2) 0.32890(18) 0.0588(5) Uani 1 1 d . . .
C17 C 0.0181(4) 0.2905(4) 0.4036(2) 0.1003(11) Uani 1 1 d . . .
H17 H 0.115 0.2184 0.3846 0.12 Uiso 1 1 calc R . .
C18 C -0.0522(6) 0.2799(4) 0.5058(3) 0.1301(17) Uani 1 1 d . . .
H18 H -0.0031 0.1985 0.5558 0.156 Uiso 1 1 calc R . .
C19 C -0.1921(5) 0.3850(4) 0.5371(2) 0.1065(12) Uani 1 1 d . . .
C20 C -0.2657(4) 0.4994(3) 0.4620(2) 0.0936(10) Uani 1 1 d . . .
H20 H -0.363 0.5707 0.4815 0.112 Uiso 1 1 calc R . .
C21 C -0.2007(3) 0.5125(3) 0.3589(2) 0.0763(7) Uani 1 1 d . . .
H21 H -0.2541 0.5913 0.3091 0.092 Uiso 1 1 calc R . .
C22 C -0.2675(7) 0.3723(5) 0.6506(3) 0.174(3) Uani 1 1 d . . .
H22A H -0.21 0.4044 0.6816 0.261 Uiso 1 1 calc R . .
H22B H -0.2589 0.2718 0.6855 0.261 Uiso 1 1 calc R . .
H22C H -0.3815 0.4325 0.6568 0.261 Uiso 1 1 calc R . .
N1 N -0.2921(2) 0.18131(18) 0.33888(12) 0.0502(4) Uani 1 1 d . . .
N2 N -0.08742(18) 0.37039(17) 0.15250(13) 0.0455(4) Uani 1 1 d . . .
O1 O 0.14323(19) -0.09718(17) 0.07527(14) 0.0722(5) Uani 1 1 d . . .
O2 O -0.1893(2) 0.0850(2) 0.38873(12) 0.0756(5) Uani 1 1 d . . .
O3 O -0.4265(2) 0.25080(18) 0.37709(12) 0.0742(5) Uani 1 1 d . . .
O4 O 0.18353(18) 0.3137(2) 0.18866(16) 0.0817(6) Uani 1 1 d . . .
O5 O 0.0019(2) 0.5726(2) 0.14419(15) 0.0790(5) Uani 1 1 d . . .
S1 S 0.02467(6) 0.42262(7) 0.19682(5) 0.05856(19) Uani 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 O1 1.207(2) . ?
C1 C2 1.498(3) . ?
C1 C12 1.498(3) . ?
C2 C3 1.535(3) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 C13 1.551(3) . ?
C3 C4 1.554(2) . ?
C3 H3 0.98 . ?
C4 C5 1.509(2) . ?
C4 C11 1.546(2) . ?
C4 N1 1.555(2) . ?
C5 C6 1.378(2) . ?
C5 C10 1.385(2) . ?
C6 C7 1.377(3) . ?
C6 H6 0.93 . ?
C7 C8 1.371(3) . ?
C7 H7 0.93 . ?
C8 C9 1.374(3) . ?
C8 H8 0.93 . ?
C9 C10 1.382(3) . ?
C9 H9 0.93 . ?
C10 N2 1.422(2) . ?
C11 N2 1.480(2) . ?
C11 C12 1.517(2) . ?
C11 H11 0.98 . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C13 C14 1.523(4) . ?
C13 C15 1.528(4) . ?
C13 H13 0.98 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?
C16 C21 1.374(3) . ?
C16 C17 1.377(4) . ?
C16 S1 1.749(2) . ?
C17 C18 1.366(5) . ?
C17 H17 0.93 . ?
C18 C19 1.365(5) . ?
C18 H18 0.93 . ?
C19 C20 1.361(4) . ?
C19 C22 1.510(5) . ?
C20 C21 1.366(4) . ?
C20 H20 0.93 . ?
C21 H21 0.93 . ?
C22 H22A 0.96 . ?
C22 H22B 0.96 . ?
C22 H22C 0.96 . ?
N1 O3 1.206(2) . ?
N1 O2 1.220(2) . ?
N2 S1 1.6399(15) . ?
O4 S1 1.4241(18) . ?
O5 S1 1.4192(19) . ?

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
O1 C1 C2 122.6(2) . . ?
O1 C1 C12 121.8(2) . . ?
C2 C1 C12 115.60(15) . . ?
C1 C2 C3 112.35(16) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
C2 C3 C13 113.23(16) . . ?
C2 C3 C4 110.79(15) . . ?
C13 C3 C4 116.61(15) . . ?
C2 C3 H3 105 . . ?
C13 C3 H3 105 . . ?
C4 C3 H3 105 . . ?
C5 C4 C11 102.63(13) . . ?
C5 C4 C3 116.42(14) . . ?
C11 C4 C3 113.35(13) . . ?
C5 C4 N1 108.54(13) . . ?
C11 C4 N1 107.58(14) . . ?
C3 C4 N1 107.91(13) . . ?
C6 C5 C10 119.63(16) . . ?
C6 C5 C4 130.34(15) . . ?
C10 C5 C4 110.02(15) . . ?
C7 C6 C5 119.22(17) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C8 C7 C6 120.41(18) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 121.48(18) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C10 117.79(18) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 H9 121.1 . . ?
C9 C10 C5 121.39(17) . . ?
C9 C10 N2 128.02(16) . . ?
C5 C10 N2 110.48(15) . . ?
N2 C11 C12 109.42(15) . . ?
N2 C11 C4 105.10(13) . . ?
C12 C11 C4 112.40(15) . . ?
N2 C11 H11 109.9 . . ?
C12 C11 H11 109.9 . . ?
C4 C11 H11 109.9 . . ?
C1 C12 C11 112.43(16) . . ?
C1 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C1 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C15 109.2(2) . . ?
C14 C13 C3 109.5(2) . . ?
C15 C13 C3 115.6(2) . . ?
C14 C13 H13 107.4 . . ?
C15 C13 H13 107.4 . . ?
C3 C13 H13 107.4 . . ?
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 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 119.2(2) . . ?
C21 C16 S1 119.93(19) . . ?
C17 C16 S1 120.7(2) . . ?
C18 C17 C16 119.2(3) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C19 C18 C17 122.2(3) . . ?
C19 C18 H18 118.9 . . ?
C17 C18 H18 118.9 . . ?
C20 C19 C18 117.6(3) . . ?
C20 C19 C22 120.8(3) . . ?
C18 C19 C22 121.5(3) . . ?
C19 C20 C21 121.8(3) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C20 C21 C16 119.8(2) . . ?
C20 C21 H21 120.1 . . ?
C16 C21 H21 120.1 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 N1 O2 124.22(17) . . ?
O3 N1 C4 118.57(16) . . ?
O2 N1 C4 117.12(15) . . ?
C10 N2 C11 108.49(13) . . ?
C10 N2 S1 123.90(12) . . ?
C11 N2 S1 118.45(12) . . ?
O5 S1 O4 121.15(12) . . ?
O5 S1 N2 106.95(10) . . ?
O4 S1 N2 104.52(9) . . ?
O5 S1 C16 108.72(11) . . ?
O4 S1 C16 107.83(12) . . ?
N2 S1 C16 106.81(9) . . ?

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 C1 C2 C3 -151.1(2) . . . . ?
C12 C1 C2 C3 27.7(3) . . . . ?
C1 C2 C3 C13 167.68(18) . . . . ?
C1 C2 C3 C4 -59.1(2) . . . . ?
C2 C3 C4 C5 149.60(15) . . . . ?
C13 C3 C4 C5 -78.9(2) . . . . ?
C2 C3 C4 C11 30.9(2) . . . . ?
C13 C3 C4 C11 162.33(17) . . . . ?
C2 C3 C4 N1 -88.15(17) . . . . ?
C13 C3 C4 N1 43.3(2) . . . . ?
C11 C4 C5 C6 165.10(17) . . . . ?
C3 C4 C5 C6 40.7(2) . . . . ?
N1 C4 C5 C6 -81.2(2) . . . . ?
C11 C4 C5 C10 -13.96(17) . . . . ?
C3 C4 C5 C10 -138.36(15) . . . . ?
N1 C4 C5 C10 99.72(16) . . . . ?
C10 C5 C6 C7 -2.4(3) . . . . ?
C4 C5 C6 C7 178.62(17) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C6 C7 C8 C9 2.0(3) . . . . ?
C7 C8 C9 C10 -2.5(3) . . . . ?
C8 C9 C10 C5 0.7(3) . . . . ?
C8 C9 C10 N2 176.48(18) . . . . ?
C6 C5 C10 C9 1.8(3) . . . . ?
C4 C5 C10 C9 -179.02(16) . . . . ?
C6 C5 C10 N2 -174.69(15) . . . . ?
C4 C5 C10 N2 4.49(19) . . . . ?
C5 C4 C11 N2 17.73(16) . . . . ?
C3 C4 C11 N2 144.13(15) . . . . ?
N1 C4 C11 N2 -96.65(15) . . . . ?
C5 C4 C11 C12 -101.19(16) . . . . ?
C3 C4 C11 C12 25.2(2) . . . . ?
N1 C4 C11 C12 144.43(15) . . . . ?
O1 C1 C12 C11 -151.04(19) . . . . ?
C2 C1 C12 C11 30.1(2) . . . . ?
N2 C11 C12 C1 -174.20(15) . . . . ?
C4 C11 C12 C1 -57.8(2) . . . . ?
C2 C3 C13 C14 -79.3(2) . . . . ?
C4 C3 C13 C14 150.4(2) . . . . ?
C2 C3 C13 C15 44.5(3) . . . . ?
C4 C3 C13 C15 -85.8(2) . . . . ?
C21 C16 C17 C18 -1.1(5) . . . . ?
S1 C16 C17 C18 -177.2(3) . . . . ?
C16 C17 C18 C19 -1.6(7) . . . . ?
C17 C18 C19 C20 3.1(7) . . . . ?
C17 C18 C19 C22 -179.5(5) . . . . ?
C18 C19 C20 C21 -1.9(6) . . . . ?
C22 C19 C20 C21 -179.4(4) . . . . ?
C19 C20 C21 C16 -0.6(5) . . . . ?
C17 C16 C21 C20 2.2(4) . . . . ?
S1 C16 C21 C20 178.3(2) . . . . ?
C5 C4 N1 O3 27.3(2) . . . . ?
C11 C4 N1 O3 137.63(18) . . . . ?
C3 C4 N1 O3 -99.73(19) . . . . ?
C5 C4 N1 O2 -155.95(17) . . . . ?
C11 C4 N1 O2 -45.6(2) . . . . ?
C3 C4 N1 O2 77.1(2) . . . . ?
C9 C10 N2 C11 -168.50(18) . . . . ?
C5 C10 N2 C11 7.69(19) . . . . ?
C9 C10 N2 S1 45.4(3) . . . . ?
C5 C10 N2 S1 -138.40(14) . . . . ?
C12 C11 N2 C10 104.78(16) . . . . ?
C4 C11 N2 C10 -16.12(18) . . . . ?
C12 C11 N2 S1 -107.00(16) . . . . ?
C4 C11 N2 S1 132.10(13) . . . . ?
C10 N2 S1 O5 -44.78(18) . . . . ?
C11 N2 S1 O5 172.22(14) . . . . ?
C10 N2 S1 O4 -174.39(16) . . . . ?
C11 N2 S1 O4 42.61(16) . . . . ?
C10 N2 S1 C16 71.49(17) . . . . ?
C11 N2 S1 C16 -71.52(15) . . . . ?
C21 C16 S1 O5 39.4(2) . . . . ?
C17 C16 S1 O5 -144.5(2) . . . . ?
C21 C16 S1 O4 172.5(2) . . . . ?
C17 C16 S1 O4 -11.4(3) . . . . ?
C21 C16 S1 N2 -75.7(2) . . . . ?
C17 C16 S1 N2 100.4(2) . . . . ?

# END of CIF
