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

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

data_ea_b
_database_code_depnum_ccdc_archive 'CCDC 2155844'
loop_
_audit_author_name
_audit_author_address
'Nathalie Gruber'
;Service de Radiocristallographie Federation de chimie
France
;
_audit_update_record             
;
2022-03-02 deposited with the CCDC.	2022-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H30 N2 O3 S'
_chemical_formula_sum            'C28 H30 N2 O3 S'
_chemical_formula_weight         474.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   10.6469(3)
_cell_length_b                   15.8266(4)
_cell_length_c                   28.9384(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4876.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9724
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      66.15

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             2016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.438
_shelx_estimated_absorpt_T_min   0.762
_shelx_estimated_absorpt_T_max   0.870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6327
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Cu-ImuS 3.0 microfocus tube'
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω shuterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52110
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.054
_diffrn_reflns_theta_max         66.565
_diffrn_reflns_theta_full        66.565
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8605
_reflns_number_gt                8115
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0504P)²+1.3595P] 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_abs_structure_details 
;
 Flack x determined using 3442 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         8605
_refine_ls_number_parameters     617
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0907
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0721(2) 0.95467(14) 0.33391(7) 0.0209(5) Uani 1 1 d . . . . .
C1 C 0.1048(3) 0.88946(16) 0.36238(9) 0.0220(6) Uani 1 1 d . . . . .
C2 C 0.1392(2) 0.83507(16) 0.38791(9) 0.0232(5) Uani 1 1 d . . . . .
C3 C 0.1843(2) 0.76751(16) 0.41872(9) 0.0227(5) Uani 1 1 d . . . . .
H3 H 0.277444 0.764009 0.414804 0.027 Uiso 1 1 calc R U . . .
N2 N 0.1324(2) 0.68344(14) 0.40711(8) 0.0267(5) Uani 1 1 d . . . . .
C4 C 0.1700(4) 0.6509(2) 0.36127(11) 0.0480(10) Uani 1 1 d . . . . .
H4 H 0.176658 0.698428 0.338603 0.058 Uiso 1 1 calc R U . . .
C5 C 0.0610(5) 0.5913(3) 0.34782(14) 0.0694(14) Uani 1 1 d . . . . .
H5A H 0.022393 0.609774 0.318373 0.083 Uiso 1 1 calc R U . . .
H5B H 0.091997 0.532775 0.344047 0.083 Uiso 1 1 calc R U . . .
C6 C -0.0346(4) 0.5959(2) 0.38704(14) 0.0567(11) Uani 1 1 d . . . . .
H6A H -0.121645 0.594578 0.374996 0.068 Uiso 1 1 calc R U . . .
H6B H -0.023066 0.548829 0.409138 0.068 Uiso 1 1 calc R U . . .
C7 C -0.0058(3) 0.67955(19) 0.40926(11) 0.0351(7) Uani 1 1 d . . . . .
H7A H -0.044380 0.726725 0.391864 0.042 Uiso 1 1 calc R U . . .
H7B H -0.035812 0.681161 0.441628 0.042 Uiso 1 1 calc R U . . .
C8 C 0.2956(5) 0.6075(3) 0.36658(12) 0.0581(12) Uani 1 1 d . . . . .
H8A H 0.316598 0.577263 0.337643 0.070 Uiso 1 1 calc R U . . .
H8B H 0.361641 0.650290 0.372237 0.070 Uiso 1 1 calc R U . . .
O1 O 0.2929(3) 0.54916(16) 0.40389(8) 0.0580(7) Uani 1 1 d . . . . .
H1A H 0.245126 0.567460 0.424708 0.087 Uiso 1 1 calc R U . . .
C9 C 0.1589(2) 0.78579(17) 0.46964(9) 0.0220(5) Uani 1 1 d . . . . .
C10 C 0.2258(3) 0.74001(19) 0.50245(10) 0.0274(6) Uani 1 1 d . . . . .
H10 H 0.284447 0.698384 0.492748 0.033 Uiso 1 1 calc R U . . .
C11 C 0.2076(3) 0.7546(2) 0.54911(10) 0.0332(7) Uani 1 1 d . . . . .
H11 H 0.254058 0.723110 0.571216 0.040 Uiso 1 1 calc R U . . .
C12 C 0.1224(3) 0.8148(2) 0.56376(10) 0.0341(7) Uani 1 1 d . . . . .
H12 H 0.109889 0.824499 0.595824 0.041 Uiso 1 1 calc R U . . .
C13 C 0.0551(3) 0.8609(2) 0.53133(10) 0.0317(7) Uani 1 1 d . . . . .
H13 H -0.003470 0.902389 0.541215 0.038 Uiso 1 1 calc R U . . .
C14 C 0.0734(3) 0.84650(18) 0.48440(10) 0.0263(6) Uani 1 1 d . . . . .
H14 H 0.027242 0.878270 0.462321 0.032 Uiso 1 1 calc R U . . .
S1 S 0.12313(6) 0.94671(4) 0.27921(2) 0.01998(14) Uani 1 1 d . . . . .
O2 O 0.24419(17) 0.90861(12) 0.28136(6) 0.0266(4) Uani 1 1 d . . . . .
O3 O 0.10789(19) 1.02931(12) 0.25993(6) 0.0267(4) Uani 1 1 d . . . . .
C15 C 0.0190(2) 0.87758(16) 0.25083(9) 0.0184(5) Uani 1 1 d . . . . .
C16 C 0.0480(3) 0.79173(17) 0.24813(9) 0.0237(6) Uani 1 1 d . . . . .
H16 H 0.122135 0.770077 0.262026 0.028 Uiso 1 1 calc R U . . .
C17 C -0.0338(3) 0.73877(17) 0.22473(10) 0.0250(6) Uani 1 1 d . . . . .
H17 H -0.014856 0.680257 0.222449 0.030 Uiso 1 1 calc R U . . .
C18 C -0.1432(3) 0.76971(17) 0.20447(9) 0.0238(6) Uani 1 1 d . . . . .
C19 C -0.1711(3) 0.85533(17) 0.20835(9) 0.0222(5) Uani 1 1 d . . . . .
H19 H -0.245878 0.876887 0.194892 0.027 Uiso 1 1 calc R U . . .
C20 C -0.0905(2) 0.90964(16) 0.23175(8) 0.0209(5) Uani 1 1 d . . . . .
H20 H -0.110169 0.967946 0.234618 0.025 Uiso 1 1 calc R U . . .
C21 C -0.2297(3) 0.71155(19) 0.17802(10) 0.0307(7) Uani 1 1 d . . . . .
H21A H -0.198958 0.705255 0.146283 0.046 Uiso 1 1 calc R U . . .
H21B H -0.314547 0.735536 0.177514 0.046 Uiso 1 1 calc R U . . .
H21C H -0.231699 0.656118 0.193090 0.046 Uiso 1 1 calc R U . . .
C22 C -0.0548(3) 0.99383(18) 0.34020(10) 0.0254(6) Uani 1 1 d . . . . .
H22A H -0.120077 0.953968 0.329309 0.030 Uiso 1 1 calc R U . . .
H22B H -0.060525 1.045708 0.321205 0.030 Uiso 1 1 calc R U . . .
C23 C -0.0790(3) 1.01563(17) 0.38995(10) 0.0235(6) Uani 1 1 d . . . . .
C24 C -0.0159(3) 1.0806(2) 0.41166(12) 0.0358(7) Uani 1 1 d . . . . .
H24 H 0.045611 1.111897 0.395153 0.043 Uiso 1 1 calc R U . . .
C25 C -0.0414(3) 1.1005(2) 0.45730(12) 0.0446(9) Uani 1 1 d . . . . .
H25 H 0.004271 1.144419 0.472076 0.053 Uiso 1 1 calc R U . . .
C26 C -0.1327(3) 1.0569(2) 0.48155(10) 0.0374(7) Uani 1 1 d . . . . .
H26 H -0.149621 1.070442 0.512923 0.045 Uiso 1 1 calc R U . . .
C27 C -0.1986(3) 0.9939(2) 0.45968(12) 0.0383(8) Uani 1 1 d . . . . .
H27 H -0.262888 0.964485 0.475817 0.046 Uiso 1 1 calc R U . . .
C28 C -0.1720(3) 0.97301(19) 0.41445(11) 0.0316(6) Uani 1 1 d . . . . .
H28 H -0.217825 0.928978 0.399809 0.038 Uiso 1 1 calc R U . . .
N3 N 0.5702(2) 0.05202(15) 0.33543(8) 0.0239(5) Uani 1 1 d . . . . .
C29 C 0.5798(3) 0.12326(17) 0.36258(10) 0.0267(6) Uani 1 1 d . . . . .
C30 C 0.5819(3) 0.18249(17) 0.38830(10) 0.0281(6) Uani 1 1 d . . . . .
C31 C 0.5929(3) 0.25553(17) 0.42049(9) 0.0252(5) Uani 1 1 d . . . . .
H31 H 0.508159 0.282503 0.422329 0.030 Uiso 1 1 calc R U . . .
N4 N 0.6806(2) 0.32020(14) 0.40313(8) 0.0236(5) Uani 1 1 d . . . . .
C32 C 0.6318(3) 0.36880(18) 0.36375(10) 0.0292(6) Uani 1 1 d . . . . .
H32 H 0.594167 0.329146 0.340687 0.035 Uiso 1 1 calc R U . . .
C33 C 0.7501(3) 0.4096(2) 0.34297(12) 0.0448(8) Uani 1 1 d . . . . .
H33A H 0.754995 0.398546 0.309339 0.054 Uiso 1 1 calc R U . . .
H33B H 0.749859 0.471400 0.348126 0.054 Uiso 1 1 calc R U . . .
C34 C 0.8604(3) 0.3681(2) 0.36825(10) 0.0341(7) Uani 1 1 d . . . . .
H34A H 0.928553 0.353431 0.346418 0.041 Uiso 1 1 calc R U . . .
H34B H 0.894305 0.405985 0.392427 0.041 Uiso 1 1 calc R U . . .
C35 C 0.8040(3) 0.28963(18) 0.38937(10) 0.0300(6) Uani 1 1 d . . . . .
H35A H 0.797522 0.243285 0.366514 0.036 Uiso 1 1 calc R U . . .
H35B H 0.853207 0.270014 0.416335 0.036 Uiso 1 1 calc R U . . .
C36 C 0.5360(3) 0.4352(2) 0.37666(12) 0.0377(7) Uani 1 1 d . . . . .
H36A H 0.566047 0.466989 0.403974 0.045 Uiso 1 1 calc R U . . .
H36B H 0.526303 0.475605 0.350783 0.045 Uiso 1 1 calc R U . . .
O4 O 0.4161(2) 0.39726(15) 0.38694(10) 0.0478(6) Uani 1 1 d . . . . .
H4A H 0.364781 0.435091 0.394516 0.072 Uiso 1 1 calc R U . . .
C37 C 0.6264(3) 0.22544(17) 0.46931(9) 0.0260(6) Uani 1 1 d . . . . .
C38 C 0.5639(3) 0.15599(18) 0.48702(10) 0.0295(6) Uani 1 1 d . . . . .
H38 H 0.509087 0.124449 0.467708 0.035 Uiso 1 1 calc R U . . .
C39 C 0.5806(3) 0.1320(2) 0.53262(11) 0.0348(7) Uani 1 1 d . . . . .
H39 H 0.534936 0.085411 0.544729 0.042 Uiso 1 1 calc R U . . .
C40 C 0.6637(3) 0.1757(2) 0.56061(10) 0.0349(7) Uani 1 1 d . . . . .
H40 H 0.675601 0.159199 0.591865 0.042 Uiso 1 1 calc R U . . .
C41 C 0.7291(3) 0.24352(19) 0.54268(10) 0.0294(6) Uani 1 1 d . . . . .
H41 H 0.786668 0.273493 0.561686 0.035 Uiso 1 1 calc R U . . .
C42 C 0.7116(3) 0.26815(18) 0.49730(10) 0.0284(6) Uani 1 1 d . . . . .
H42 H 0.757965 0.314406 0.485177 0.034 Uiso 1 1 calc R U . . .
S2 S 0.62823(6) 0.06031(4) 0.28192(2) 0.02555(16) Uani 1 1 d . . . . .
O5 O 0.74705(19) 0.10139(14) 0.28617(8) 0.0360(5) Uani 1 1 d . . . . .
O6 O 0.6192(2) -0.02260(13) 0.26254(8) 0.0353(5) Uani 1 1 d . . . . .
C43 C 0.5268(3) 0.12766(17) 0.25141(9) 0.0212(5) Uani 1 1 d . . . . .
C44 C 0.5532(3) 0.21344(17) 0.24919(9) 0.0248(6) Uani 1 1 d . . . . .
H44 H 0.626719 0.235574 0.263324 0.030 Uiso 1 1 calc R U . . .
C45 C 0.4707(3) 0.26630(17) 0.22606(10) 0.0268(6) Uani 1 1 d . . . . .
H45 H 0.488322 0.325060 0.224351 0.032 Uiso 1 1 calc R U . . .
C46 C 0.3627(3) 0.23492(17) 0.20532(9) 0.0229(5) Uani 1 1 d . . . . .
C47 C 0.3377(3) 0.14865(17) 0.20844(9) 0.0249(6) Uani 1 1 d . . . . .
H47 H 0.263702 0.126545 0.194640 0.030 Uiso 1 1 calc R U . . .
C48 C 0.4188(3) 0.09470(17) 0.23132(9) 0.0235(6) Uani 1 1 d . . . . .
H48 H 0.401009 0.035997 0.233280 0.028 Uiso 1 1 calc R U . . .
C49 C 0.2735(3) 0.29289(19) 0.18036(9) 0.0301(7) Uani 1 1 d . . . . .
H49A H 0.296279 0.351757 0.186678 0.045 Uiso 1 1 calc R U . . .
H49B H 0.187582 0.282388 0.191111 0.045 Uiso 1 1 calc R U . . .
H49C H 0.278408 0.282264 0.147048 0.045 Uiso 1 1 calc R U . . .
C50 C 0.4480(3) 0.00569(17) 0.33991(10) 0.0266(6) Uani 1 1 d . . . . .
H50A H 0.451908 -0.047381 0.321853 0.032 Uiso 1 1 calc R U . . .
H50B H 0.379420 0.040824 0.327089 0.032 Uiso 1 1 calc R U . . .
C51 C 0.4201(3) -0.01461(17) 0.38989(10) 0.0247(6) Uani 1 1 d . . . . .
C52 C 0.3268(3) 0.02885(18) 0.41298(11) 0.0307(6) Uani 1 1 d . . . . .
H52 H 0.281994 0.072318 0.397454 0.037 Uiso 1 1 calc R U . . .
C53 C 0.2974(3) 0.00987(19) 0.45869(12) 0.0326(7) Uani 1 1 d . . . . .
H53 H 0.232676 0.039989 0.474186 0.039 Uiso 1 1 calc R U . . .
C54 C 0.3631(3) -0.0532(2) 0.48145(11) 0.0345(7) Uani 1 1 d . . . . .
H54 H 0.345158 -0.065795 0.512870 0.041 Uiso 1 1 calc R U . . .
C55 C 0.4548(3) -0.0977(2) 0.45804(12) 0.0408(8) Uani 1 1 d . . . . .
H55 H 0.498774 -0.141894 0.473290 0.049 Uiso 1 1 calc R U . . .
C56 C 0.4833(3) -0.0786(2) 0.41267(11) 0.0352(7) Uani 1 1 d . . . . .
H56 H 0.546679 -0.109568 0.396998 0.042 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.366(3) . ?
N1 C22 1.498(3) . ?
N1 S1 1.678(2) . ?
C1 C2 1.192(4) . ?
C2 C3 1.473(3) . ?
C3 N2 1.479(3) . ?
C3 C9 1.526(3) . ?
C3 H3 1.0000 . ?
N2 C7 1.473(4) . ?
N2 C4 1.478(4) . ?
C4 C8 1.511(5) . ?
C4 C5 1.546(6) . ?
C4 H4 1.0000 . ?
C5 C6 1.527(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.503(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O1 1.421(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
O1 H1A 0.8400 . ?
C9 C10 1.390(4) . ?
C9 C14 1.391(4) . ?
C10 C11 1.384(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
S1 O2 1.424(2) . ?
S1 O3 1.431(2) . ?
S1 C15 1.761(3) . ?
C15 C20 1.386(4) . ?
C15 C16 1.396(4) . ?
C16 C17 1.385(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.394(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.392(4) . ?
C18 C21 1.510(4) . ?
C19 C20 1.391(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.503(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.379(4) . ?
C23 C28 1.392(4) . ?
C24 C25 1.385(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.375(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.379(4) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
N3 C29 1.378(4) . ?
N3 C50 1.499(4) . ?
N3 S2 1.672(2) . ?
C29 C30 1.197(4) . ?
C30 C31 1.489(4) . ?
C31 N4 1.473(3) . ?
C31 C37 1.533(4) . ?
C31 H31 1.0000 . ?
N4 C35 1.455(4) . ?
N4 C32 1.470(4) . ?
C32 C36 1.512(4) . ?
C32 C33 1.537(4) . ?
C32 H32 1.0000 . ?
C33 C34 1.531(5) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.509(4) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 O4 1.442(4) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
O4 H4A 0.8400 . ?
C37 C38 1.383(4) . ?
C37 C42 1.392(4) . ?
C38 C39 1.385(4) . ?
C38 H38 0.9500 . ?
C39 C40 1.385(5) . ?
C39 H39 0.9500 . ?
C40 C41 1.381(4) . ?
C40 H40 0.9500 . ?
C41 C42 1.383(4) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
S2 O5 1.428(2) . ?
S2 O6 1.430(2) . ?
S2 C43 1.755(3) . ?
C43 C44 1.388(4) . ?
C43 C48 1.390(4) . ?
C44 C45 1.386(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.389(4) . ?
C45 H45 0.9500 . ?
C46 C47 1.394(4) . ?
C46 C49 1.506(4) . ?
C47 C48 1.383(4) . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 C51 1.511(4) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 C52 1.381(4) . ?
C51 C56 1.382(4) . ?
C52 C53 1.392(5) . ?
C52 H52 0.9500 . ?
C53 C54 1.386(4) . ?
C53 H53 0.9500 . ?
C54 C55 1.382(5) . ?
C54 H54 0.9500 . ?
C55 C56 1.381(5) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C22 118.0(2) . . ?
C1 N1 S1 115.46(18) . . ?
C22 N1 S1 115.95(17) . . ?
C2 C1 N1 176.3(3) . . ?
C1 C2 C3 178.6(3) . . ?
C2 C3 N2 113.2(2) . . ?
C2 C3 C9 112.9(2) . . ?
N2 C3 C9 108.9(2) . . ?
C2 C3 H3 107.2 . . ?
N2 C3 H3 107.2 . . ?
C9 C3 H3 107.2 . . ?
C7 N2 C4 107.1(3) . . ?
C7 N2 C3 113.6(2) . . ?
C4 N2 C3 114.5(2) . . ?
N2 C4 C8 107.9(3) . . ?
N2 C4 C5 103.6(3) . . ?
C8 C4 C5 114.3(3) . . ?
N2 C4 H4 110.3 . . ?
C8 C4 H4 110.3 . . ?
C5 C4 H4 110.3 . . ?
C6 C5 C4 106.5(3) . . ?
C6 C5 H5A 110.4 . . ?
C4 C5 H5A 110.4 . . ?
C6 C5 H5B 110.4 . . ?
C4 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
C7 C6 C5 102.9(3) . . ?
C7 C6 H6A 111.2 . . ?
C5 C6 H6A 111.2 . . ?
C7 C6 H6B 111.2 . . ?
C5 C6 H6B 111.2 . . ?
H6A C6 H6B 109.1 . . ?
N2 C7 C6 102.9(3) . . ?
N2 C7 H7A 111.2 . . ?
C6 C7 H7A 111.2 . . ?
N2 C7 H7B 111.2 . . ?
C6 C7 H7B 111.2 . . ?
H7A C7 H7B 109.1 . . ?
O1 C8 C4 110.8(3) . . ?
O1 C8 H8A 109.5 . . ?
C4 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C8 O1 H1A 109.5 . . ?
C10 C9 C14 119.1(3) . . ?
C10 C9 C3 118.0(2) . . ?
C14 C9 C3 122.9(2) . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 120.1(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 120.3(3) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
O2 S1 O3 120.43(12) . . ?
O2 S1 N1 106.46(11) . . ?
O3 S1 N1 105.23(11) . . ?
O2 S1 C15 109.08(12) . . ?
O3 S1 C15 108.33(12) . . ?
N1 S1 C15 106.44(12) . . ?
C20 C15 C16 121.3(2) . . ?
C20 C15 S1 119.19(19) . . ?
C16 C15 S1 119.5(2) . . ?
C17 C16 C15 118.5(3) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C16 C17 C18 121.2(3) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C19 C18 C17 119.1(2) . . ?
C19 C18 C21 120.3(3) . . ?
C17 C18 C21 120.6(3) . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C15 C20 C19 119.1(2) . . ?
C15 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
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 . . ?
N1 C22 C23 111.5(2) . . ?
N1 C22 H22A 109.3 . . ?
C23 C22 H22A 109.3 . . ?
N1 C22 H22B 109.3 . . ?
C23 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C24 C23 C28 118.4(3) . . ?
C24 C23 C22 121.6(3) . . ?
C28 C23 C22 119.9(3) . . ?
C23 C24 C25 120.6(3) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C26 C25 C24 120.6(3) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C27 C26 C25 119.2(3) . . ?
C27 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
C26 C27 C28 120.4(3) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C23 120.9(3) . . ?
C27 C28 H28 119.6 . . ?
C23 C28 H28 119.6 . . ?
C29 N3 C50 114.6(2) . . ?
C29 N3 S2 115.85(19) . . ?
C50 N3 S2 116.05(18) . . ?
C30 C29 N3 175.2(3) . . ?
C29 C30 C31 176.5(3) . . ?
N4 C31 C30 112.1(2) . . ?
N4 C31 C37 112.5(2) . . ?
C30 C31 C37 110.7(2) . . ?
N4 C31 H31 107.1 . . ?
C30 C31 H31 107.1 . . ?
C37 C31 H31 107.1 . . ?
C35 N4 C32 106.3(2) . . ?
C35 N4 C31 115.7(2) . . ?
C32 N4 C31 113.8(2) . . ?
N4 C32 C36 114.2(2) . . ?
N4 C32 C33 103.5(2) . . ?
C36 C32 C33 111.0(3) . . ?
N4 C32 H32 109.3 . . ?
C36 C32 H32 109.3 . . ?
C33 C32 H32 109.3 . . ?
C34 C33 C32 105.1(2) . . ?
C34 C33 H33A 110.7 . . ?
C32 C33 H33A 110.7 . . ?
C34 C33 H33B 110.7 . . ?
C32 C33 H33B 110.7 . . ?
H33A C33 H33B 108.8 . . ?
C35 C34 C33 104.0(3) . . ?
C35 C34 H34A 111.0 . . ?
C33 C34 H34A 111.0 . . ?
C35 C34 H34B 111.0 . . ?
C33 C34 H34B 111.0 . . ?
H34A C34 H34B 109.0 . . ?
N4 C35 C34 101.3(2) . . ?
N4 C35 H35A 111.5 . . ?
C34 C35 H35A 111.5 . . ?
N4 C35 H35B 111.5 . . ?
C34 C35 H35B 111.5 . . ?
H35A C35 H35B 109.3 . . ?
O4 C36 C32 111.0(3) . . ?
O4 C36 H36A 109.4 . . ?
C32 C36 H36A 109.4 . . ?
O4 C36 H36B 109.4 . . ?
C32 C36 H36B 109.4 . . ?
H36A C36 H36B 108.0 . . ?
C36 O4 H4A 109.5 . . ?
C38 C37 C42 118.9(3) . . ?
C38 C37 C31 118.5(3) . . ?
C42 C37 C31 122.5(2) . . ?
C37 C38 C39 120.6(3) . . ?
C37 C38 H38 119.7 . . ?
C39 C38 H38 119.7 . . ?
C38 C39 C40 120.1(3) . . ?
C38 C39 H39 119.9 . . ?
C40 C39 H39 119.9 . . ?
C41 C40 C39 119.4(3) . . ?
C41 C40 H40 120.3 . . ?
C39 C40 H40 120.3 . . ?
C40 C41 C42 120.5(3) . . ?
C40 C41 H41 119.7 . . ?
C42 C41 H41 119.7 . . ?
C41 C42 C37 120.3(3) . . ?
C41 C42 H42 119.9 . . ?
C37 C42 H42 119.9 . . ?
O5 S2 O6 120.76(13) . . ?
O5 S2 N3 106.46(13) . . ?
O6 S2 N3 105.43(13) . . ?
O5 S2 C43 108.17(13) . . ?
O6 S2 C43 108.56(13) . . ?
N3 S2 C43 106.63(12) . . ?
C44 C43 C48 121.0(2) . . ?
C44 C43 S2 119.5(2) . . ?
C48 C43 S2 119.4(2) . . ?
C45 C44 C43 119.0(3) . . ?
C45 C44 H44 120.5 . . ?
C43 C44 H44 120.5 . . ?
C44 C45 C46 121.2(3) . . ?
C44 C45 H45 119.4 . . ?
C46 C45 H45 119.4 . . ?
C45 C46 C47 118.7(3) . . ?
C45 C46 C49 120.8(2) . . ?
C47 C46 C49 120.5(3) . . ?
C48 C47 C46 121.1(3) . . ?
C48 C47 H47 119.5 . . ?
C46 C47 H47 119.5 . . ?
C47 C48 C43 119.0(2) . . ?
C47 C48 H48 120.5 . . ?
C43 C48 H48 120.5 . . ?
C46 C49 H49A 109.5 . . ?
C46 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C46 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
N3 C50 C51 110.9(2) . . ?
N3 C50 H50A 109.5 . . ?
C51 C50 H50A 109.5 . . ?
N3 C50 H50B 109.5 . . ?
C51 C50 H50B 109.5 . . ?
H50A C50 H50B 108.0 . . ?
C52 C51 C56 118.9(3) . . ?
C52 C51 C50 119.9(3) . . ?
C56 C51 C50 121.1(3) . . ?
C51 C52 C53 120.9(3) . . ?
C51 C52 H52 119.5 . . ?
C53 C52 H52 119.5 . . ?
C54 C53 C52 119.6(3) . . ?
C54 C53 H53 120.2 . . ?
C52 C53 H53 120.2 . . ?
C55 C54 C53 119.4(3) . . ?
C55 C54 H54 120.3 . . ?
C53 C54 H54 120.3 . . ?
C56 C55 C54 120.6(3) . . ?
C56 C55 H55 119.7 . . ?
C54 C55 H55 119.7 . . ?
C55 C56 C51 120.5(3) . . ?
C55 C56 H56 119.8 . . ?
C51 C56 H56 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 N2 C7 -59.5(3) . . . . ?
C9 C3 N2 C7 67.0(3) . . . . ?
C2 C3 N2 C4 64.1(3) . . . . ?
C9 C3 N2 C4 -169.5(2) . . . . ?
C7 N2 C4 C8 -147.8(3) . . . . ?
C3 N2 C4 C8 85.2(3) . . . . ?
C7 N2 C4 C5 -26.2(3) . . . . ?
C3 N2 C4 C5 -153.2(3) . . . . ?
N2 C4 C5 C6 1.5(4) . . . . ?
C8 C4 C5 C6 118.7(3) . . . . ?
C4 C5 C6 C7 22.6(4) . . . . ?
C4 N2 C7 C6 41.3(3) . . . . ?
C3 N2 C7 C6 168.8(2) . . . . ?
C5 C6 C7 N2 -38.3(3) . . . . ?
N2 C4 C8 O1 50.1(4) . . . . ?
C5 C4 C8 O1 -64.5(4) . . . . ?
C2 C3 C9 C10 -162.6(2) . . . . ?
N2 C3 C9 C10 70.8(3) . . . . ?
C2 C3 C9 C14 16.7(4) . . . . ?
N2 C3 C9 C14 -109.9(3) . . . . ?
C14 C9 C10 C11 0.0(4) . . . . ?
C3 C9 C10 C11 179.3(3) . . . . ?
C9 C10 C11 C12 0.2(5) . . . . ?
C10 C11 C12 C13 -0.3(5) . . . . ?
C11 C12 C13 C14 0.1(5) . . . . ?
C12 C13 C14 C9 0.1(5) . . . . ?
C10 C9 C14 C13 -0.1(4) . . . . ?
C3 C9 C14 C13 -179.4(3) . . . . ?
C1 N1 S1 O2 -36.2(2) . . . . ?
C22 N1 S1 O2 179.73(19) . . . . ?
C1 N1 S1 O3 -165.10(19) . . . . ?
C22 N1 S1 O3 50.8(2) . . . . ?
C1 N1 S1 C15 80.1(2) . . . . ?
C22 N1 S1 C15 -64.0(2) . . . . ?
O2 S1 C15 C20 -159.7(2) . . . . ?
O3 S1 C15 C20 -27.0(2) . . . . ?
N1 S1 C15 C20 85.8(2) . . . . ?
O2 S1 C15 C16 20.5(2) . . . . ?
O3 S1 C15 C16 153.3(2) . . . . ?
N1 S1 C15 C16 -94.0(2) . . . . ?
C20 C15 C16 C17 1.7(4) . . . . ?
S1 C15 C16 C17 -178.5(2) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C16 C17 C18 C19 -0.7(4) . . . . ?
C16 C17 C18 C21 178.4(3) . . . . ?
C17 C18 C19 C20 0.6(4) . . . . ?
C21 C18 C19 C20 -178.5(2) . . . . ?
C16 C15 C20 C19 -1.8(4) . . . . ?
S1 C15 C20 C19 178.4(2) . . . . ?
C18 C19 C20 C15 0.7(4) . . . . ?
C1 N1 C22 C23 49.6(3) . . . . ?
S1 N1 C22 C23 -167.27(19) . . . . ?
N1 C22 C23 C24 70.3(3) . . . . ?
N1 C22 C23 C28 -113.4(3) . . . . ?
C28 C23 C24 C25 2.5(5) . . . . ?
C22 C23 C24 C25 178.8(3) . . . . ?
C23 C24 C25 C26 -1.6(5) . . . . ?
C24 C25 C26 C27 -0.4(5) . . . . ?
C25 C26 C27 C28 1.5(5) . . . . ?
C26 C27 C28 C23 -0.5(5) . . . . ?
C24 C23 C28 C27 -1.4(5) . . . . ?
C22 C23 C28 C27 -177.9(3) . . . . ?
C30 C31 N4 C35 -51.4(3) . . . . ?
C37 C31 N4 C35 74.2(3) . . . . ?
C30 C31 N4 C32 72.2(3) . . . . ?
C37 C31 N4 C32 -162.2(2) . . . . ?
C35 N4 C32 C36 -154.9(2) . . . . ?
C31 N4 C32 C36 76.5(3) . . . . ?
C35 N4 C32 C33 -34.1(3) . . . . ?
C31 N4 C32 C33 -162.7(2) . . . . ?
N4 C32 C33 C34 9.1(3) . . . . ?
C36 C32 C33 C34 132.1(3) . . . . ?
C32 C33 C34 C35 17.6(3) . . . . ?
C32 N4 C35 C34 45.5(3) . . . . ?
C31 N4 C35 C34 173.0(2) . . . . ?
C33 C34 C35 N4 -37.9(3) . . . . ?
N4 C32 C36 O4 -75.5(3) . . . . ?
C33 C32 C36 O4 167.9(3) . . . . ?
N4 C31 C37 C38 -170.3(2) . . . . ?
C30 C31 C37 C38 -44.0(3) . . . . ?
N4 C31 C37 C42 13.5(4) . . . . ?
C30 C31 C37 C42 139.8(3) . . . . ?
C42 C37 C38 C39 3.5(4) . . . . ?
C31 C37 C38 C39 -172.9(3) . . . . ?
C37 C38 C39 C40 -2.3(5) . . . . ?
C38 C39 C40 C41 0.3(5) . . . . ?
C39 C40 C41 C42 0.4(4) . . . . ?
C40 C41 C42 C37 0.9(4) . . . . ?
C38 C37 C42 C41 -2.8(4) . . . . ?
C31 C37 C42 C41 173.4(3) . . . . ?
C29 N3 S2 O5 44.9(2) . . . . ?
C50 N3 S2 O5 -176.43(19) . . . . ?
C29 N3 S2 O6 174.3(2) . . . . ?
C50 N3 S2 O6 -47.0(2) . . . . ?
C29 N3 S2 C43 -70.4(2) . . . . ?
C50 N3 S2 C43 68.3(2) . . . . ?
O5 S2 C43 C44 -20.5(3) . . . . ?
O6 S2 C43 C44 -153.2(2) . . . . ?
N3 S2 C43 C44 93.7(2) . . . . ?
O5 S2 C43 C48 161.9(2) . . . . ?
O6 S2 C43 C48 29.2(3) . . . . ?
N3 S2 C43 C48 -83.9(2) . . . . ?
C48 C43 C44 C45 -0.8(4) . . . . ?
S2 C43 C44 C45 -178.3(2) . . . . ?
C43 C44 C45 C46 0.1(4) . . . . ?
C44 C45 C46 C47 0.5(4) . . . . ?
C44 C45 C46 C49 179.8(3) . . . . ?
C45 C46 C47 C48 -0.6(4) . . . . ?
C49 C46 C47 C48 -179.9(3) . . . . ?
C46 C47 C48 C43 0.0(4) . . . . ?
C44 C43 C48 C47 0.7(4) . . . . ?
S2 C43 C48 C47 178.2(2) . . . . ?
C29 N3 C50 C51 -53.5(3) . . . . ?
S2 N3 C50 C51 167.32(19) . . . . ?
N3 C50 C51 C52 107.6(3) . . . . ?
N3 C50 C51 C56 -75.0(3) . . . . ?
C56 C51 C52 C53 1.0(4) . . . . ?
C50 C51 C52 C53 178.4(3) . . . . ?
C51 C52 C53 C54 0.3(5) . . . . ?
C52 C53 C54 C55 -1.5(5) . . . . ?
C53 C54 C55 C56 1.4(5) . . . . ?
C54 C55 C56 C51 -0.1(5) . . . . ?
C52 C51 C56 C55 -1.1(5) . . . . ?
C50 C51 C56 C55 -178.5(3) . . . . ?

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether'
