# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1985233'
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO UMR CNRS Universite Paris Saclay Universite Paris Saclay FRANCE
France
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-08-11 downloaded from the CCDC.
;

#ZIM266_v773_GuillotICMMO

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H21 N3 O4 S2'
_chemical_formula_sum            'C17 H21 N3 O4 S2'
_chemical_melting_point          ?


_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         395.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0189 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.823(11)
_cell_length_b                   14.91(2)
_cell_length_c                   17.77(3)
_cell_angle_alpha                66.73(6)
_cell_angle_beta                 84.29(5)
_cell_angle_gamma                75.73(5)
_cell_volume                     2789(7)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9806
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      67.45
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    2.843
_shelx_estimated_absorpt_T_min   0.554
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7386
_exptl_absorpt_correction_T_max  0.9528
_exptl_absorpt_process_details   'Bruker APEX3'
_diffrn_radiation_probe          neutron
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30314
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.706
_diffrn_reflns_theta_max         67.658
_diffrn_reflns_theta_full        67.658
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             9707
_reflns_number_gt                7902
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'

_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1152P)²+1.6099P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9707
_refine_ls_number_parameters     706
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1779
_refine_ls_wR_factor_gt          0.1656
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5928(3) 0.1161(2) 0.2516(2) 0.0264(7) Uani 1 1 d . . . . .
H1 H 0.575507 0.121941 0.303015 0.032 Uiso 1 1 calc R U . . .
C2 C 0.5196(3) 0.1756(3) 0.1857(2) 0.0319(8) Uani 1 1 d . . . . .
H2 H 0.453202 0.223502 0.191586 0.038 Uiso 1 1 calc R U . . .
C3 C 0.5429(3) 0.1656(3) 0.1111(2) 0.0324(8) Uani 1 1 d . . . . .
H3 H 0.491765 0.205767 0.066147 0.039 Uiso 1 1 calc R U . . .
C4 C 0.6398(3) 0.0979(3) 0.1021(2) 0.0274(7) Uani 1 1 d . . . . .
H4 H 0.655509 0.090804 0.051024 0.033 Uiso 1 1 calc R U . . .
C5 C 0.7151(3) 0.0394(2) 0.1679(2) 0.0215(7) Uani 1 1 d . . . . .
H5 H 0.783077 -0.006525 0.161291 0.026 Uiso 1 1 calc R U . . .
C6 C 0.6911(3) 0.0480(2) 0.24276(19) 0.0195(6) Uani 1 1 d . . . . .
C7 C 0.7693(3) -0.0145(2) 0.3161(2) 0.0244(7) Uani 1 1 d . . . . .
H7A H 0.820058 0.026324 0.321754 0.029 Uiso 1 1 calc R U . . .
H7B H 0.720240 -0.032351 0.366004 0.029 Uiso 1 1 calc R U . . .
C8 C 0.7841(2) -0.1753(2) 0.31618(17) 0.0165(6) Uani 1 1 d . . . . .
C9 C 0.8091(2) -0.3413(2) 0.32002(18) 0.0161(6) Uani 1 1 d . . . . .
C10 C 0.9069(3) -0.4332(2) 0.3227(2) 0.0207(6) Uani 1 1 d . . . . .
H10A H 0.986190 -0.420172 0.316446 0.025 Uiso 1 1 calc R U . . .
H10B H 0.894839 -0.462094 0.283417 0.025 Uiso 1 1 calc R U . . .
C11 C 0.7607(3) -0.3893(2) 0.40697(19) 0.0208(6) Uani 1 1 d . . . . .
H11A H 0.680087 -0.397557 0.407184 0.025 Uiso 1 1 calc R U . . .
H11B H 0.766546 -0.354188 0.442997 0.025 Uiso 1 1 calc R U . . .
C12 C 0.7179(2) -0.3140(2) 0.25421(18) 0.0158(6) Uani 1 1 d . . . . .
C13 C 0.6478(2) -0.2144(2) 0.11513(17) 0.0154(6) Uani 1 1 d . . . . .
C14 C 0.6929(3) -0.1439(2) 0.03366(18) 0.0187(6) Uani 1 1 d . . . . .
H14A H 0.760712 -0.120299 0.040963 0.022 Uiso 1 1 calc R U . . .
H14B H 0.631052 -0.086682 0.001488 0.022 Uiso 1 1 calc R U . . .
C15 C 0.6485(3) -0.2992(2) 0.08599(18) 0.0190(6) Uani 1 1 d . . . . .
H15A H 0.569647 -0.301609 0.073826 0.023 Uiso 1 1 calc R U . . .
H15B H 0.690664 -0.365891 0.123484 0.023 Uiso 1 1 calc R U . . .
C16 C 0.5263(2) -0.1631(2) 0.13545(17) 0.0159(6) Uani 1 1 d . . . . .
C17 C 0.4169(3) -0.0525(2) 0.2014(2) 0.0229(7) Uani 1 1 d . . . . .
H17A H 0.381394 -0.003880 0.149176 0.034 Uiso 1 1 calc R U . . .
H17B H 0.436187 -0.016858 0.232651 0.034 Uiso 1 1 calc R U . . .
H17C H 0.361894 -0.093352 0.232889 0.034 Uiso 1 1 calc R U . . .
N1 N 0.8572(2) -0.25601(19) 0.30894(15) 0.0159(5) Uani 1 1 d . . . . .
H1A H 0.931677 -0.257323 0.297873 0.019 Uiso 1 1 calc R U . . .
N2 N 0.7316(2) -0.24345(19) 0.18050(15) 0.0151(5) Uani 1 1 d . . . . .
H2A H 0.791041 -0.214695 0.171527 0.018 Uiso 1 1 calc R U . . .
N3 N 0.5223(2) -0.1168(2) 0.18605(16) 0.0195(5) Uani 1 1 d . . . . .
H3A H 0.586666 -0.125421 0.211483 0.023 Uiso 1 1 calc R U . . .
O1 O 0.84122(17) -0.10470(16) 0.31101(13) 0.0192(5) Uani 1 1 d . . . . .
O2 O 0.67893(17) -0.16604(16) 0.32504(13) 0.0194(5) Uani 1 1 d . . . . .
O3 O 0.63732(17) -0.35744(16) 0.26922(13) 0.0181(4) Uani 1 1 d . . . . .
O4 O 0.44006(17) -0.16045(17) 0.09992(13) 0.0213(5) Uani 1 1 d . . . . .
S1 S 0.87100(8) -0.50645(7) 0.42876(5) 0.0316(2) Uani 1 1 d . . . . .
S2 S 0.73252(6) -0.24316(7) -0.00623(5) 0.0240(2) Uani 1 1 d . . . . .
C18 C 0.3007(3) 0.4665(3) 0.0473(2) 0.0265(7) Uani 1 1 d . . . . .
H18 H 0.313169 0.397163 0.081070 0.032 Uiso 1 1 calc R U . . .
C19 C 0.2214(3) 0.5079(3) -0.0172(2) 0.0304(8) Uani 1 1 d . . . . .
H19 H 0.179753 0.466872 -0.027332 0.037 Uiso 1 1 calc R U . . .
C20 C 0.2034(3) 0.6091(3) -0.0666(2) 0.0287(8) Uani 1 1 d . . . . .
H20 H 0.149394 0.637258 -0.110617 0.034 Uiso 1 1 calc R U . . .
C21 C 0.2637(3) 0.6688(3) -0.0520(2) 0.0287(7) Uani 1 1 d . . . . .
H21 H 0.251198 0.738068 -0.085853 0.034 Uiso 1 1 calc R U . . .
C22 C 0.3429(3) 0.6275(3) 0.0123(2) 0.0240(7) Uani 1 1 d . . . . .
H22 H 0.384558 0.668736 0.022083 0.029 Uiso 1 1 calc R U . . .
C23 C 0.3614(3) 0.5261(2) 0.06235(19) 0.0201(6) Uani 1 1 d . . . . .
C24 C 0.4486(3) 0.4792(2) 0.13137(19) 0.0203(6) Uani 1 1 d . . . . .
H24A H 0.421657 0.423105 0.175535 0.024 Uiso 1 1 calc R U . . .
H24B H 0.524324 0.450962 0.111035 0.024 Uiso 1 1 calc R U . . .
C25 C 0.3770(2) 0.5775(2) 0.20914(17) 0.0139(6) Uani 1 1 d . . . . .
C26 C 0.3237(2) 0.6567(2) 0.30535(17) 0.0144(6) Uani 1 1 d . . . . .
C27 C 0.3754(3) 0.7098(2) 0.34846(18) 0.0187(6) Uani 1 1 d . . . . .
H27A H 0.321189 0.771485 0.349790 0.022 Uiso 1 1 calc R U . . .
H27B H 0.452307 0.723480 0.326265 0.022 Uiso 1 1 calc R U . . .
C28 C 0.3055(3) 0.5663(2) 0.38312(19) 0.0222(7) Uani 1 1 d . . . . .
H28A H 0.344189 0.500684 0.380384 0.027 Uiso 1 1 calc R U . . .
H28B H 0.222480 0.568500 0.398998 0.027 Uiso 1 1 calc R U . . .
C29 C 0.2104(2) 0.7227(2) 0.26172(18) 0.0149(6) Uani 1 1 d . . . . .
C30 C 0.1202(2) 0.8637(2) 0.14420(18) 0.0148(6) Uani 1 1 d . . . . .
C31 C 0.0622(3) 0.9374(2) 0.18543(18) 0.0173(6) Uani 1 1 d . . . . .
H31A H 0.108492 0.931367 0.231314 0.021 Uiso 1 1 calc R U . . .
H31B H -0.019099 0.933185 0.203157 0.021 Uiso 1 1 calc R U . . .
C32 C 0.1518(2) 0.9448(2) 0.06259(18) 0.0173(6) Uani 1 1 d . . . . .
H32A H 0.119265 0.944472 0.013511 0.021 Uiso 1 1 calc R U . . .
H32B H 0.236620 0.941867 0.055801 0.021 Uiso 1 1 calc R U . . .
C33 C 0.0344(2) 0.8119(2) 0.12654(17) 0.0155(6) Uani 1 1 d . . . . .
C34 C 0.0139(3) 0.6742(3) 0.0909(2) 0.0244(7) Uani 1 1 d . . . . .
H34A H -0.041185 0.648485 0.134557 0.037 Uiso 1 1 calc R U . . .
H34B H 0.067088 0.618165 0.081002 0.037 Uiso 1 1 calc R U . . .
H34C H -0.029179 0.719881 0.040679 0.037 Uiso 1 1 calc R U . . .
N4 N 0.4077(2) 0.62911(18) 0.24835(15) 0.0144(5) Uani 1 1 d . . . . .
H4A H 0.475891 0.645389 0.239735 0.017 Uiso 1 1 calc R U . . .
N5 N 0.2227(2) 0.79184(18) 0.18569(15) 0.0141(5) Uani 1 1 d . . . . .
H5A H 0.291826 0.792710 0.162285 0.017 Uiso 1 1 calc R U . . .
N6 N 0.0808(2) 0.7279(2) 0.11557(16) 0.0193(5) Uani 1 1 d . . . . .
H6 H 0.156242 0.702950 0.123599 0.023 Uiso 1 1 calc R U . . .
O5 O 0.46614(17) 0.54824(16) 0.16524(13) 0.0172(4) Uani 1 1 d . . . . .
O6 O 0.28064(17) 0.56117(16) 0.21279(13) 0.0180(4) Uani 1 1 d . . . . .
O7 O 0.11468(17) 0.71840(16) 0.29484(13) 0.0177(4) Uani 1 1 d . . . . .
O8 O -0.07099(17) 0.85171(16) 0.11873(13) 0.0179(4) Uani 1 1 d . . . . .
S3 S 0.38522(9) 0.60357(7) 0.44569(5) 0.0384(2) Uani 1 1 d . . . . .
S4 S 0.07128(7) 1.04729(6) 0.09260(5) 0.0249(2) Uani 1 1 d . . . . .
C35 C 0.2488(3) 0.2374(3) 0.2930(2) 0.0272(7) Uani 1 1 d . . . . .
H35 H 0.311066 0.190342 0.327341 0.033 Uiso 1 1 calc R U . . .
C36 C 0.2272(3) 0.3364(3) 0.2830(2) 0.0314(8) Uani 1 1 d . . . . .
H36 H 0.274327 0.357226 0.310390 0.038 Uiso 1 1 calc R U . . .
C37 C 0.1374(3) 0.4054(3) 0.2334(3) 0.0372(9) Uani 1 1 d . . . . .
H37 H 0.121822 0.473578 0.227178 0.045 Uiso 1 1 calc R U . . .
C38 C 0.0703(3) 0.3754(3) 0.1929(3) 0.0409(10) Uani 1 1 d . . . . .
H38 H 0.008321 0.422962 0.158568 0.049 Uiso 1 1 calc R U . . .
C39 C 0.0930(3) 0.2752(3) 0.2022(3) 0.0332(8) Uani 1 1 d . . . . .
H39 H 0.047753 0.255127 0.172981 0.040 Uiso 1 1 calc R U . . .
C40 C 0.1809(3) 0.2050(3) 0.2535(2) 0.0236(7) Uani 1 1 d . . . . .
C41 C 0.1980(3) 0.0965(3) 0.2689(2) 0.0264(7) Uani 1 1 d . . . . .
H41A H 0.196630 0.087587 0.216715 0.032 Uiso 1 1 calc R U . . .
H41B H 0.273963 0.058159 0.296030 0.032 Uiso 1 1 calc R U . . .
C42 C 0.1266(3) -0.0337(2) 0.37828(19) 0.0197(6) Uani 1 1 d . . . . .
C43 C 0.0433(3) -0.1525(2) 0.48941(18) 0.0169(6) Uani 1 1 d . . . . .
C44 C 0.0422(3) -0.2317(2) 0.45410(18) 0.0190(6) Uani 1 1 d . . . . .
H44A H 0.117100 -0.281884 0.461554 0.023 Uiso 1 1 calc R U . . .
H44B H 0.017353 -0.201936 0.396117 0.023 Uiso 1 1 calc R U . . .
C45 C -0.0718(3) -0.1635(2) 0.5388(2) 0.0227(7) Uani 1 1 d . . . . .
H45A H -0.139361 -0.108215 0.512503 0.027 Uiso 1 1 calc R U . . .
H45B H -0.064683 -0.173132 0.596644 0.027 Uiso 1 1 calc R U . . .
C46 C 0.1429(3) -0.1756(2) 0.54796(18) 0.0180(6) Uani 1 1 d . . . . .
C47 C 0.3075(3) -0.2985(2) 0.63110(19) 0.0196(6) Uani 1 1 d . . . . .
C48 C 0.2623(3) -0.2960(2) 0.71516(19) 0.0225(7) Uani 1 1 d . . . . .
H48A H 0.183732 -0.251955 0.712602 0.027 Uiso 1 1 calc R U . . .
H48B H 0.317711 -0.280116 0.743718 0.027 Uiso 1 1 calc R U . . .
C49 C 0.3497(3) -0.4132(2) 0.6631(2) 0.0248(7) Uani 1 1 d . . . . .
H49A H 0.434633 -0.436725 0.674125 0.030 Uiso 1 1 calc R U . . .
H49B H 0.326473 -0.442836 0.627728 0.030 Uiso 1 1 calc R U . . .
C50 C 0.4087(3) -0.2465(3) 0.5948(2) 0.0263(7) Uani 1 1 d . . . . .
C51 C 0.5044(4) -0.1445(4) 0.4750(3) 0.0519(12) Uani 1 1 d . . . . .
H51A H 0.496796 -0.085715 0.488730 0.078 Uiso 1 1 calc R U . . .
H51B H 0.500154 -0.123141 0.415471 0.078 Uiso 1 1 calc R U . . .
H51C H 0.579608 -0.190940 0.494789 0.078 Uiso 1 1 calc R U . . .
N7 N 0.0353(2) -0.05270(19) 0.42756(15) 0.0191(5) Uani 1 1 d . . . . .
H7 H -0.028515 -0.005472 0.422514 0.023 Uiso 1 1 calc R U . . .
N8 N 0.2124(2) -0.26755(19) 0.57371(16) 0.0189(5) Uani 1 1 d . . . . .
H8 H 0.200088 -0.311112 0.555264 0.023 Uiso 1 1 calc R U . . .
N9 N 0.4098(3) -0.1947(2) 0.51390(19) 0.0322(7) Uani 1 1 d . . . . .
H9 H 0.352740 -0.190705 0.483647 0.039 Uiso 1 1 calc R U . . .
O9 O 0.10253(19) 0.06176(16) 0.32176(14) 0.0235(5) Uani 1 1 d . . . . .
O10 O 0.2186(2) -0.09313(17) 0.38123(14) 0.0251(5) Uani 1 1 d . . . . .
O11 O 0.15583(18) -0.11075(16) 0.57116(13) 0.0208(5) Uani 1 1 d . . . . .
O12 O 0.4875(2) -0.2582(2) 0.64012(17) 0.0396(7) Uani 1 1 d . . . . .
S5 S -0.07138(8) -0.27948(7) 0.52568(6) 0.0305(2) Uani 1 1 d . . . . .
S6 S 0.26158(8) -0.42968(6) 0.75546(5) 0.0279(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.381(5) . ?
C1 C6 1.383(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.386(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.370(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.510(5) . ?
C7 O1 1.435(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O2 1.218(4) . ?
C8 N1 1.341(4) . ?
C8 O1 1.354(4) . ?
C9 N1 1.454(4) . ?
C9 C12 1.535(4) . ?
C9 C11 1.543(5) . ?
C9 C10 1.548(5) . ?
C10 S1 1.836(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 S1 1.829(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O3 1.230(4) . ?
C12 N2 1.343(4) . ?
C13 N2 1.463(4) . ?
C13 C16 1.533(4) . ?
C13 C15 1.541(5) . ?
C13 C14 1.551(4) . ?
C14 S2 1.825(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 S2 1.837(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O4 1.237(4) . ?
C16 N3 1.325(4) . ?
C17 N3 1.447(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N1 H1A 0.8800 . ?
N2 H2A 0.8800 . ?
N3 H3A 0.8800 . ?
C18 C23 1.383(5) . ?
C18 C19 1.395(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.379(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.392(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.508(5) . ?
C24 O5 1.443(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 O6 1.213(4) . ?
C25 O5 1.337(4) . ?
C25 N4 1.349(4) . ?
C26 N4 1.452(4) . ?
C26 C29 1.523(4) . ?
C26 C28 1.545(5) . ?
C26 C27 1.549(4) . ?
C27 S3 1.815(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 S3 1.841(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 O7 1.226(4) . ?
C29 N5 1.358(4) . ?
C30 N5 1.440(4) . ?
C30 C33 1.538(4) . ?
C30 C31 1.542(4) . ?
C30 C32 1.560(4) . ?
C31 S4 1.826(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 S4 1.831(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 O8 1.236(4) . ?
C33 N6 1.320(4) . ?
C34 N6 1.453(4) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
N4 H4A 0.8800 . ?
N5 H5A 0.8800 . ?
N6 H6 0.8800 . ?
C35 C36 1.376(6) . ?
C35 C40 1.394(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.376(6) . ?
C36 H36 0.9500 . ?
C37 C38 1.375(6) . ?
C37 H37 0.9500 . ?
C38 C39 1.396(6) . ?
C38 H38 0.9500 . ?
C39 C40 1.380(5) . ?
C39 H39 0.9500 . ?
C40 C41 1.494(5) . ?
C41 O9 1.455(4) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 O10 1.212(4) . ?
C42 N7 1.334(4) . ?
C42 O9 1.357(4) . ?
C43 N7 1.445(4) . ?
C43 C46 1.532(4) . ?
C43 C44 1.543(5) . ?
C43 C45 1.552(4) . ?
C44 S5 1.829(4) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 S5 1.833(4) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 O11 1.236(4) . ?
C46 N8 1.337(4) . ?
C47 N8 1.456(4) . ?
C47 C50 1.534(5) . ?
C47 C49 1.538(5) . ?
C47 C48 1.547(5) . ?
C48 S6 1.834(4) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 S6 1.819(4) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 O12 1.227(4) . ?
C50 N9 1.337(5) . ?
C51 N9 1.463(5) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
N7 H7 0.8800 . ?
N8 H8 0.8800 . ?
N9 H9 0.8800 . ?

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 120.2(3) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C1 C2 C3 120.1(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 C7 122.1(3) . . ?
C1 C6 C7 118.3(3) . . ?
O1 C7 C6 113.4(3) . . ?
O1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
O1 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
O2 C8 N1 124.1(3) . . ?
O2 C8 O1 124.2(3) . . ?
N1 C8 O1 111.8(3) . . ?
N1 C9 C12 111.3(3) . . ?
N1 C9 C11 113.3(3) . . ?
C12 C9 C11 111.5(3) . . ?
N1 C9 C10 111.2(2) . . ?
C12 C9 C10 111.7(3) . . ?
C11 C9 C10 97.1(3) . . ?
C9 C10 S1 92.0(2) . . ?
C9 C10 H10A 113.3 . . ?
S1 C10 H10A 113.3 . . ?
C9 C10 H10B 113.3 . . ?
S1 C10 H10B 113.3 . . ?
H10A C10 H10B 110.6 . . ?
C9 C11 S1 92.5(2) . . ?
C9 C11 H11A 113.2 . . ?
S1 C11 H11A 113.2 . . ?
C9 C11 H11B 113.2 . . ?
S1 C11 H11B 113.2 . . ?
H11A C11 H11B 110.6 . . ?
O3 C12 N2 122.4(3) . . ?
O3 C12 C9 120.3(3) . . ?
N2 C12 C9 117.3(3) . . ?
N2 C13 C16 111.9(2) . . ?
N2 C13 C15 113.5(3) . . ?
C16 C13 C15 114.4(2) . . ?
N2 C13 C14 109.6(2) . . ?
C16 C13 C14 110.1(3) . . ?
C15 C13 C14 96.2(3) . . ?
C13 C14 S2 91.9(2) . . ?
C13 C14 H14A 113.3 . . ?
S2 C14 H14A 113.3 . . ?
C13 C14 H14B 113.3 . . ?
S2 C14 H14B 113.3 . . ?
H14A C14 H14B 110.6 . . ?
C13 C15 S2 91.8(2) . . ?
C13 C15 H15A 113.3 . . ?
S2 C15 H15A 113.3 . . ?
C13 C15 H15B 113.3 . . ?
S2 C15 H15B 113.3 . . ?
H15A C15 H15B 110.6 . . ?
O4 C16 N3 123.8(3) . . ?
O4 C16 C13 119.4(3) . . ?
N3 C16 C13 116.6(3) . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C8 N1 C9 117.7(3) . . ?
C8 N1 H1A 121.2 . . ?
C9 N1 H1A 121.2 . . ?
C12 N2 C13 119.9(2) . . ?
C12 N2 H2A 120.0 . . ?
C13 N2 H2A 120.0 . . ?
C16 N3 C17 123.1(3) . . ?
C16 N3 H3A 118.5 . . ?
C17 N3 H3A 118.5 . . ?
C8 O1 C7 115.6(3) . . ?
C11 S1 C10 78.40(16) . . ?
C14 S2 C15 77.88(17) . . ?
C23 C18 C19 120.2(3) . . ?
C23 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 120.1(3) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.0(4) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C23 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C18 C23 C22 119.4(3) . . ?
C18 C23 C24 119.3(3) . . ?
C22 C23 C24 121.3(3) . . ?
O5 C24 C23 113.8(3) . . ?
O5 C24 H24A 108.8 . . ?
C23 C24 H24A 108.8 . . ?
O5 C24 H24B 108.8 . . ?
C23 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
O6 C25 O5 124.8(3) . . ?
O6 C25 N4 124.1(3) . . ?
O5 C25 N4 111.1(2) . . ?
N4 C26 C29 110.7(3) . . ?
N4 C26 C28 113.5(3) . . ?
C29 C26 C28 113.4(2) . . ?
N4 C26 C27 110.6(2) . . ?
C29 C26 C27 110.9(3) . . ?
C28 C26 C27 97.0(3) . . ?
C26 C27 S3 92.0(2) . . ?
C26 C27 H27A 113.3 . . ?
S3 C27 H27A 113.3 . . ?
C26 C27 H27B 113.3 . . ?
S3 C27 H27B 113.3 . . ?
H27A C27 H27B 110.6 . . ?
C26 C28 S3 91.2(2) . . ?
C26 C28 H28A 113.4 . . ?
S3 C28 H28A 113.4 . . ?
C26 C28 H28B 113.4 . . ?
S3 C28 H28B 113.4 . . ?
H28A C28 H28B 110.7 . . ?
O7 C29 N5 122.0(3) . . ?
O7 C29 C26 122.4(3) . . ?
N5 C29 C26 115.5(2) . . ?
N5 C30 C33 111.2(3) . . ?
N5 C30 C31 114.2(3) . . ?
C33 C30 C31 113.3(2) . . ?
N5 C30 C32 111.7(2) . . ?
C33 C30 C32 109.6(3) . . ?
C31 C30 C32 95.9(3) . . ?
C30 C31 S4 93.0(2) . . ?
C30 C31 H31A 113.1 . . ?
S4 C31 H31A 113.1 . . ?
C30 C31 H31B 113.1 . . ?
S4 C31 H31B 113.1 . . ?
H31A C31 H31B 110.5 . . ?
C30 C32 S4 92.2(2) . . ?
C30 C32 H32A 113.2 . . ?
S4 C32 H32A 113.2 . . ?
C30 C32 H32B 113.2 . . ?
S4 C32 H32B 113.2 . . ?
H32A C32 H32B 110.6 . . ?
O8 C33 N6 123.3(3) . . ?
O8 C33 C30 120.3(3) . . ?
N6 C33 C30 116.3(3) . . ?
N6 C34 H34A 109.5 . . ?
N6 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
N6 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C25 N4 C26 117.3(2) . . ?
C25 N4 H4A 121.3 . . ?
C26 N4 H4A 121.3 . . ?
C29 N5 C30 118.5(2) . . ?
C29 N5 H5A 120.7 . . ?
C30 N5 H5A 120.7 . . ?
C33 N6 C34 123.5(3) . . ?
C33 N6 H6 118.2 . . ?
C34 N6 H6 118.2 . . ?
C25 O5 C24 115.4(2) . . ?
C27 S3 C28 78.66(18) . . ?
C31 S4 C32 78.12(18) . . ?
C36 C35 C40 121.0(3) . . ?
C36 C35 H35 119.5 . . ?
C40 C35 H35 119.5 . . ?
C35 C36 C37 120.1(4) . . ?
C35 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
C38 C37 C36 119.9(4) . . ?
C38 C37 H37 120.1 . . ?
C36 C37 H37 120.1 . . ?
C37 C38 C39 120.1(4) . . ?
C37 C38 H38 120.0 . . ?
C39 C38 H38 120.0 . . ?
C40 C39 C38 120.5(4) . . ?
C40 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?
C39 C40 C35 118.4(3) . . ?
C39 C40 C41 120.2(3) . . ?
C35 C40 C41 121.3(3) . . ?
O9 C41 C40 106.6(3) . . ?
O9 C41 H41A 110.4 . . ?
C40 C41 H41A 110.4 . . ?
O9 C41 H41B 110.4 . . ?
C40 C41 H41B 110.4 . . ?
H41A C41 H41B 108.6 . . ?
O10 C42 N7 125.6(3) . . ?
O10 C42 O9 123.5(3) . . ?
N7 C42 O9 110.9(3) . . ?
N7 C43 C46 108.6(3) . . ?
N7 C43 C44 113.5(3) . . ?
C46 C43 C44 117.1(3) . . ?
N7 C43 C45 112.2(3) . . ?
C46 C43 C45 109.4(3) . . ?
C44 C43 C45 95.5(2) . . ?
C43 C44 S5 92.4(2) . . ?
C43 C44 H44A 113.2 . . ?
S5 C44 H44A 113.2 . . ?
C43 C44 H44B 113.2 . . ?
S5 C44 H44B 113.2 . . ?
H44A C44 H44B 110.6 . . ?
C43 C45 S5 92.0(2) . . ?
C43 C45 H45A 113.3 . . ?
S5 C45 H45A 113.3 . . ?
C43 C45 H45B 113.3 . . ?
S5 C45 H45B 113.3 . . ?
H45A C45 H45B 110.6 . . ?
O11 C46 N8 121.9(3) . . ?
O11 C46 C43 120.1(3) . . ?
N8 C46 C43 118.0(3) . . ?
N8 C47 C50 113.4(3) . . ?
N8 C47 C49 108.8(3) . . ?
C50 C47 C49 111.3(3) . . ?
N8 C47 C48 111.7(3) . . ?
C50 C47 C48 115.1(3) . . ?
C49 C47 C48 95.0(3) . . ?
C47 C48 S6 91.2(2) . . ?
C47 C48 H48A 113.4 . . ?
S6 C48 H48A 113.4 . . ?
C47 C48 H48B 113.4 . . ?
S6 C48 H48B 113.4 . . ?
H48A C48 H48B 110.7 . . ?
C47 C49 S6 92.1(2) . . ?
C47 C49 H49A 113.3 . . ?
S6 C49 H49A 113.3 . . ?
C47 C49 H49B 113.3 . . ?
S6 C49 H49B 113.3 . . ?
H49A C49 H49B 110.6 . . ?
O12 C50 N9 122.9(3) . . ?
O12 C50 C47 119.0(3) . . ?
N9 C50 C47 118.0(3) . . ?
N9 C51 H51A 109.5 . . ?
N9 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
N9 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C42 N7 C43 118.6(3) . . ?
C42 N7 H7 120.7 . . ?
C43 N7 H7 120.7 . . ?
C46 N8 C47 122.6(3) . . ?
C46 N8 H8 118.7 . . ?
C47 N8 H8 118.7 . . ?
C50 N9 C51 120.9(3) . . ?
C50 N9 H9 119.6 . . ?
C51 N9 H9 119.6 . . ?
C42 O9 C41 117.0(3) . . ?
C44 S5 C45 77.43(16) . . ?
C49 S6 C48 77.01(16) . . ?

_refine_diff_density_max         1.240
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.109

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1985234'
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO UMR CNRS Universite Paris Saclay Universite Paris Saclay FRANCE
France
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-08-11 downloaded from the CCDC.
;
#zim171_v690_GuillotICMMO

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C13 H16 N2 O3 S'
_chemical_formula_sum            'C13 H16 N2 O3 S'
_chemical_melting_point          ?


_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         280.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.685(3)
_cell_length_b                   8.736(4)
_cell_length_c                   9.845(4)
_cell_angle_alpha                93.793(12)
_cell_angle_beta                 115.772(9)
_cell_angle_gamma                100.572(12)
_cell_volume                     652.2(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9340
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      31.53
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.254
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9163
_exptl_absorpt_correction_T_max  0.9462
_exptl_absorpt_process_details   'Bruker APEX3'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52952
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.329
_diffrn_reflns_theta_max         31.562
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4369
_reflns_number_gt                3437
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+0.1831P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4369
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0990
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.61601(15) 0.84144(15) 0.66960(13) 0.0163(2) Uani 1 1 d . . . . .
H1 H 1.527667 0.768327 0.679828 0.020 Uiso 1 1 calc R U . . .
C2 C 1.73800(16) 0.95599(15) 0.79376(14) 0.0184(2) Uani 1 1 d . . . . .
H2 H 1.731636 0.961178 0.887821 0.022 Uiso 1 1 calc R U . . .
C3 C 1.86879(16) 1.06259(15) 0.78083(14) 0.0182(2) Uani 1 1 d . . . . .
H3 H 1.951985 1.140442 0.865723 0.022 Uiso 1 1 calc R U . . .
C4 C 1.87720(16) 1.05465(15) 0.64287(14) 0.0180(2) Uani 1 1 d . . . . .
H4 H 1.966787 1.126946 0.633513 0.022 Uiso 1 1 calc R U . . .
C5 C 1.75482(15) 0.94114(15) 0.51848(13) 0.0175(2) Uani 1 1 d . . . . .
H5 H 1.760998 0.936725 0.424346 0.021 Uiso 1 1 calc R U . . .
C6 C 1.62273(14) 0.83344(14) 0.53075(13) 0.0136(2) Uani 1 1 d . . . . .
C7 C 1.49225(14) 0.71546(15) 0.39156(13) 0.0159(2) Uani 1 1 d . . . . .
H7A H 1.429647 0.770956 0.307008 0.019 Uiso 1 1 calc R U . . .
H7B H 1.553975 0.648852 0.357802 0.019 Uiso 1 1 calc R U . . .
C8 C 1.21508(14) 0.53927(13) 0.31178(12) 0.0120(2) Uani 1 1 d . . . . .
C9 C 0.92831(14) 0.37844(13) 0.26225(12) 0.0111(2) Uani 1 1 d . . . . .
C10 C 0.85371(15) 0.25473(14) 0.33540(13) 0.0144(2) Uani 1 1 d . . . . .
H10A H 0.785094 0.293795 0.382466 0.017 Uiso 1 1 calc R U . . .
H10B H 0.943285 0.205627 0.408057 0.017 Uiso 1 1 calc R U . . .
C11 C 0.89276(15) 0.25956(14) 0.12329(13) 0.0148(2) Uani 1 1 d . . . . .
H11A H 0.992824 0.211776 0.138511 0.018 Uiso 1 1 calc R U . . .
H11B H 0.850213 0.301797 0.025939 0.018 Uiso 1 1 calc R U . . .
C12 C 0.81960(13) 0.50524(13) 0.22502(12) 0.0114(2) Uani 1 1 d . . . . .
C13 C 0.67136(16) 0.67179(14) 0.04747(14) 0.0171(2) Uani 1 1 d . . . . .
H13A H 0.625643 0.672424 -0.062659 0.026 Uiso 1 1 calc R U . . .
H13B H 0.745834 0.776093 0.103640 0.026 Uiso 1 1 calc R U . . .
H13C H 0.572951 0.646396 0.072433 0.026 Uiso 1 1 calc R U . . .
N1 N 1.11098(12) 0.45655(11) 0.36323(10) 0.01221(18) Uani 1 1 d . . . . .
H10 H 1.154699 0.449412 0.461067 0.015 Uiso 1 1 calc R U . . .
N2 N 0.77506(12) 0.55337(11) 0.09062(10) 0.01295(19) Uani 1 1 d . . . . .
H2A H 0.808651 0.513168 0.026571 0.016 Uiso 1 1 calc R U . . .
O1 O 1.36837(10) 0.61842(10) 0.42984(9) 0.01528(17) Uani 1 1 d . . . . .
O2 O 1.17682(11) 0.54332(10) 0.17707(9) 0.01604(17) Uani 1 1 d . . . . .
O3 O 0.78196(11) 0.56237(10) 0.32199(9) 0.01813(18) Uani 1 1 d . . . . .
S1 S 0.71649(4) 0.13009(4) 0.14779(3) 0.01856(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.3912(17) . ?
C1 C2 1.3932(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.3882(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3893(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3905(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3983(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.5028(17) . ?
C7 O1 1.4417(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O2 1.2239(14) . ?
C8 N1 1.3428(15) . ?
C8 O1 1.3460(14) . ?
C9 N1 1.4534(15) . ?
C9 C10 1.5355(16) . ?
C9 C11 1.5403(16) . ?
C9 C12 1.5457(16) . ?
C10 S1 1.8333(13) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 S1 1.8446(13) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O3 1.2393(14) . ?
C12 N2 1.3286(14) . ?
C13 N2 1.4591(15) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N1 H10 0.8800 . ?
N2 H2A 0.8800 . ?

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 120.42(11) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 120.39(11) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.55(11) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.17(11) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.57(11) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.91(11) . . ?
C1 C6 C7 122.96(10) . . ?
C5 C6 C7 118.12(10) . . ?
O1 C7 C6 108.58(9) . . ?
O1 C7 H7A 110.0 . . ?
C6 C7 H7A 110.0 . . ?
O1 C7 H7B 110.0 . . ?
C6 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
O2 C8 N1 125.23(10) . . ?
O2 C8 O1 124.47(10) . . ?
N1 C8 O1 110.31(10) . . ?
N1 C9 C10 111.88(9) . . ?
N1 C9 C11 116.83(9) . . ?
C10 C9 C11 94.48(9) . . ?
N1 C9 C12 108.32(9) . . ?
C10 C9 C12 109.48(9) . . ?
C11 C9 C12 115.11(9) . . ?
C9 C10 S1 90.52(7) . . ?
C9 C10 H10A 113.6 . . ?
S1 C10 H10A 113.6 . . ?
C9 C10 H10B 113.5 . . ?
S1 C10 H10B 113.6 . . ?
H10A C10 H10B 110.8 . . ?
C9 C11 S1 89.95(7) . . ?
C9 C11 H11A 113.7 . . ?
S1 C11 H11A 113.7 . . ?
C9 C11 H11B 113.7 . . ?
S1 C11 H11B 113.7 . . ?
H11A C11 H11B 110.9 . . ?
O3 C12 N2 122.17(10) . . ?
O3 C12 C9 119.60(9) . . ?
N2 C12 C9 118.18(10) . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 N1 C9 122.00(9) . . ?
C8 N1 H10 119.0 . . ?
C9 N1 H10 119.0 . . ?
C12 N2 C13 121.10(10) . . ?
C12 N2 H2A 119.5 . . ?
C13 N2 H2A 119.5 . . ?
C8 O1 C7 116.42(9) . . ?
C10 S1 C11 75.76(6) . . ?

_refine_diff_density_max         0.494
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1985235'
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO UMR CNRS Universite Paris Saclay Universite Paris Saclay FRANCE
France
;
_audit_update_record             
;
2020-02-20 deposited with the CCDC.	2020-08-11 downloaded from the CCDC.
;

#ZIM316_v839_GuillotICMMO

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C21 H26 N4 O5 S3'
_chemical_formula_sum            'C21 H26 N4 O5 S3'
_chemical_melting_point          ?


_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         510.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0031 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0109 0.0061 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration .

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

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

_cell_length_a                   9.3649(6)
_cell_length_b                   16.1291(11)
_cell_length_c                   15.8386(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.398(2)
_cell_angle_gamma                90
_cell_volume                     2327.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9813
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      30.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.360
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9019
_exptl_absorpt_correction_T_max  0.9461
_exptl_absorpt_process_details   'Bruker APEX3'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            85926
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_av_R_equivalents  0.1345
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.319
_diffrn_reflns_theta_max         30.562
_diffrn_reflns_theta_full        30.562
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7138
_reflns_number_gt                4971
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'

_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0413P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7138
_refine_ls_number_parameters     287
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0802
_refine_ls_wR_factor_gt          0.0751
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.12780(16) 0.44264(9) 0.15090(8) 0.0157(3) Uani 1 1 d . . . . .
H1 H 0.067096 0.455473 0.095593 0.019 Uiso 1 1 calc R U . . .
C2 C 0.16540(17) 0.36058(9) 0.17242(9) 0.0203(3) Uani 1 1 d . . . . .
H2 H 0.131005 0.317603 0.131782 0.024 Uiso 1 1 calc R U . . .
C3 C 0.25326(17) 0.34170(9) 0.25337(10) 0.0217(3) Uani 1 1 d . . . . .
H3 H 0.279488 0.285737 0.268038 0.026 Uiso 1 1 calc R U . . .
C4 C 0.30263(16) 0.40405(9) 0.31266(9) 0.0189(3) Uani 1 1 d . . . . .
H4 H 0.362203 0.391005 0.368223 0.023 Uiso 1 1 calc R U . . .
C5 C 0.26511(15) 0.48572(9) 0.29093(8) 0.0142(3) Uani 1 1 d . . . . .
H5 H 0.298978 0.528436 0.331983 0.017 Uiso 1 1 calc R U . . .
C6 C 0.17838(14) 0.50589(8) 0.20967(8) 0.0114(3) Uani 1 1 d . . . . .
C7 C 0.14487(15) 0.59505(8) 0.18510(8) 0.0149(3) Uani 1 1 d . . . . .
H7A H 0.037678 0.601921 0.162862 0.018 Uiso 1 1 calc R U . . .
H7B H 0.175898 0.630465 0.237185 0.018 Uiso 1 1 calc R U . . .
C8 C 0.36648(14) 0.62906(7) 0.14550(8) 0.0095(2) Uani 1 1 d . . . . .
C9 C 0.58718(14) 0.63303(8) 0.09282(7) 0.0090(2) Uani 1 1 d . . . . .
C10 C 0.64302(15) 0.64294(8) 0.00842(8) 0.0140(3) Uani 1 1 d . . . . .
H10A H 0.709006 0.691106 0.009656 0.017 Uiso 1 1 calc R U . . .
H10B H 0.563151 0.643577 -0.044907 0.017 Uiso 1 1 calc R U . . .
C11 C 0.63410(15) 0.54162(8) 0.11036(8) 0.0141(3) Uani 1 1 d . . . . .
H11A H 0.550673 0.502324 0.097215 0.017 Uiso 1 1 calc R U . . .
H11B H 0.694845 0.532104 0.169595 0.017 Uiso 1 1 calc R U . . .
C12 C 0.67647(14) 0.68990(8) 0.16390(7) 0.0092(2) Uani 1 1 d . . . . .
C13 C 0.69326(14) 0.82471(8) 0.23584(7) 0.0085(2) Uani 1 1 d . . . . .
C14 C 0.61682(15) 0.91015(8) 0.21808(8) 0.0108(3) Uani 1 1 d . . . . .
H14A H 0.615865 0.941586 0.271633 0.013 Uiso 1 1 calc R U . . .
H14B H 0.516844 0.906911 0.180103 0.013 Uiso 1 1 calc R U . . .
C15 C 0.84046(15) 0.85380(8) 0.21695(8) 0.0124(3) Uani 1 1 d . . . . .
H15A H 0.878542 0.815753 0.178287 0.015 Uiso 1 1 calc R U . . .
H15B H 0.917014 0.865704 0.270114 0.015 Uiso 1 1 calc R U . . .
C16 C 0.71006(14) 0.79460(8) 0.33015(7) 0.0087(2) Uani 1 1 d . . . . .
C17 C 0.66918(14) 0.68685(8) 0.42903(7) 0.0092(3) Uani 1 1 d . . . . .
C18 C 0.56981(14) 0.61001(8) 0.42775(8) 0.0108(3) Uani 1 1 d . . . . .
H18A H 0.618777 0.564197 0.465069 0.013 Uiso 1 1 calc R U . . .
H18B H 0.525628 0.589660 0.368479 0.013 Uiso 1 1 calc R U . . .
C19 C 0.60412(14) 0.73637(8) 0.49418(8) 0.0114(3) Uani 1 1 d . . . . .
H19A H 0.580912 0.794582 0.476331 0.014 Uiso 1 1 calc R U . . .
H19B H 0.664746 0.733854 0.554297 0.014 Uiso 1 1 calc R U . . .
C20 C 0.83147(14) 0.66324(8) 0.46130(8) 0.0101(3) Uani 1 1 d . . . . .
C21 C 1.05121(17) 0.61051(10) 0.42188(9) 0.0236(3) Uani 1 1 d . . . . .
H21A H 1.051316 0.552640 0.403048 0.035 Uiso 1 1 calc R U . . .
H21B H 1.090883 0.613772 0.484730 0.035 Uiso 1 1 calc R U . . .
H21C H 1.112143 0.643779 0.392114 0.035 Uiso 1 1 calc R U . . .
N1 N 0.43076(12) 0.64734(7) 0.07941(6) 0.009 Uani 1 1 d D . . . .
H10 H 0.3778(15) 0.6450(8) 0.0288(8) 0.011 Uiso 1 1 d D U . . .
N2 N 0.61762(12) 0.76457(6) 0.17225(6) 0.008 Uani 1 1 d D . . . .
H20 H 0.5414(14) 0.7799(8) 0.1362(8) 0.010 Uiso 1 1 d D U . . .
N3 N 0.64004(12) 0.72511(6) 0.34323(6) 0.008 Uani 1 1 d D . . . .
H30 H 0.5844(15) 0.6985(8) 0.3020(8) 0.011 Uiso 1 1 d D U . . .
N4 N 0.90199(13) 0.64215(7) 0.40075(7) 0.014 Uani 1 1 d D . . . .
H40 H 0.8570(17) 0.6465(9) 0.3486(8) 0.018 Uiso 1 1 d D U . . .
O1 O 0.22036(10) 0.62144(6) 0.11901(5) 0.0127(2) Uani 1 1 d . . . . .
O2 O 0.43479(10) 0.62142(6) 0.22078(5) 0.0127(2) Uani 1 1 d . . . . .
O3 O 0.79550(10) 0.66746(6) 0.20922(5) 0.01284(19) Uani 1 1 d . . . . .
O4 O 0.78878(10) 0.83443(6) 0.38963(5) 0.0132(2) Uani 1 1 d . . . . .
O5 O 0.88577(10) 0.65840(6) 0.54016(5) 0.0144(2) Uani 1 1 d . . . . .
S1 S 0.74072(4) 0.54347(2) 0.02725(2) 0.01983(9) Uani 1 1 d . . . . .
S2 S 0.75494(4) 0.94747(2) 0.16176(2) 0.01575(8) Uani 1 1 d . . . . .
S3 S 0.44099(4) 0.66896(2) 0.47602(2) 0.01517(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.3883(18) . ?
C1 C2 1.392(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3919(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.5038(18) . ?
C7 O1 1.4559(15) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O2 1.2217(14) . ?
C8 O1 1.3407(15) . ?
C8 N1 1.3554(16) . ?
C9 N1 1.4491(17) . ?
C9 C12 1.5401(17) . ?
C9 C11 1.5452(18) . ?
C9 C10 1.5524(17) . ?
C10 S1 1.8367(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 S1 1.8274(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O3 1.2321(15) . ?
C12 N2 1.3437(16) . ?
C13 N2 1.4582(15) . ?
C13 C16 1.5435(16) . ?
C13 C14 1.5484(18) . ?
C13 C15 1.5495(18) . ?
C14 S2 1.8347(13) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 S2 1.8340(13) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O4 1.2337(14) . ?
C16 N3 1.3388(16) . ?
C17 N3 1.4596(15) . ?
C17 C20 1.5349(18) . ?
C17 C19 1.5380(17) . ?
C17 C18 1.5471(18) . ?
C18 S3 1.8361(13) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 S3 1.8426(13) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 O5 1.2372(14) . ?
C20 N4 1.3285(16) . ?
C21 N4 1.4520(18) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N1 H10 0.840(11) . ?
N2 H20 0.842(11) . ?
N3 H30 0.852(11) . ?
N4 H40 0.838(12) . ?

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 120.46(12) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 119.83(13) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.14(14) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.85(13) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.78(13) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.92(12) . . ?
C1 C6 C7 120.72(11) . . ?
C5 C6 C7 120.32(12) . . ?
O1 C7 C6 111.01(11) . . ?
O1 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
O1 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
O2 C8 O1 124.18(11) . . ?
O2 C8 N1 123.36(12) . . ?
O1 C8 N1 112.46(10) . . ?
N1 C9 C12 111.81(10) . . ?
N1 C9 C11 114.46(11) . . ?
C12 C9 C11 110.68(10) . . ?
N1 C9 C10 112.84(10) . . ?
C12 C9 C10 109.51(10) . . ?
C11 C9 C10 96.58(10) . . ?
C9 C10 S1 91.42(8) . . ?
C9 C10 H10A 113.4 . . ?
S1 C10 H10A 113.4 . . ?
C9 C10 H10B 113.4 . . ?
S1 C10 H10B 113.4 . . ?
H10A C10 H10B 110.7 . . ?
C9 C11 S1 92.00(8) . . ?
C9 C11 H11A 113.3 . . ?
S1 C11 H11A 113.3 . . ?
C9 C11 H11B 113.3 . . ?
S1 C11 H11B 113.3 . . ?
H11A C11 H11B 110.6 . . ?
O3 C12 N2 122.84(11) . . ?
O3 C12 C9 121.04(11) . . ?
N2 C12 C9 116.11(11) . . ?
N2 C13 C16 112.54(10) . . ?
N2 C13 C14 109.66(10) . . ?
C16 C13 C14 113.26(10) . . ?
N2 C13 C15 112.31(10) . . ?
C16 C13 C15 112.73(10) . . ?
C14 C13 C15 95.16(10) . . ?
C13 C14 S2 91.83(8) . . ?
C13 C14 H14A 113.3 . . ?
S2 C14 H14A 113.3 . . ?
C13 C14 H14B 113.3 . . ?
S2 C14 H14B 113.3 . . ?
H14A C14 H14B 110.6 . . ?
C13 C15 S2 91.82(8) . . ?
C13 C15 H15A 113.3 . . ?
S2 C15 H15A 113.3 . . ?
C13 C15 H15B 113.3 . . ?
S2 C15 H15B 113.3 . . ?
H15A C15 H15B 110.6 . . ?
O4 C16 N3 123.04(11) . . ?
O4 C16 C13 118.95(11) . . ?
N3 C16 C13 117.99(10) . . ?
N3 C17 C20 111.84(10) . . ?
N3 C17 C19 112.79(10) . . ?
C20 C17 C19 114.90(10) . . ?
N3 C17 C18 110.14(10) . . ?
C20 C17 C18 110.60(10) . . ?
C19 C17 C18 95.41(10) . . ?
C17 C18 S3 91.77(8) . . ?
C17 C18 H18A 113.3 . . ?
S3 C18 H18A 113.3 . . ?
C17 C18 H18B 113.3 . . ?
S3 C18 H18B 113.3 . . ?
H18A C18 H18B 110.7 . . ?
C17 C19 S3 91.82(8) . . ?
C17 C19 H19A 113.3 . . ?
S3 C19 H19A 113.3 . . ?
C17 C19 H19B 113.3 . . ?
S3 C19 H19B 113.3 . . ?
H19A C19 H19B 110.6 . . ?
O5 C20 N4 123.77(12) . . ?
O5 C20 C17 119.70(11) . . ?
N4 C20 C17 116.28(11) . . ?
N4 C21 H21A 109.5 . . ?
N4 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N4 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C8 N1 C9 117.83(10) . . ?
C8 N1 H10 117.2(10) . . ?
C9 N1 H10 119.1(10) . . ?
C12 N2 C13 121.30(11) . . ?
C12 N2 H20 120.0(9) . . ?
C13 N2 H20 118.2(9) . . ?
C16 N3 C17 120.36(10) . . ?
C16 N3 H30 122.5(9) . . ?
C17 N3 H30 116.8(9) . . ?
C20 N4 C21 122.44(11) . . ?
C20 N4 H40 118.0(11) . . ?
C21 N4 H40 119.6(11) . . ?
C8 O1 C7 115.61(10) . . ?
C11 S1 C10 78.26(6) . . ?
C15 S2 C14 77.12(6) . . ?
C18 S3 C19 76.68(6) . . ?

_refine_diff_density_max         0.375
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.061

