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

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

data_1
_audit_block_doi                 10.5517/ccdc.csd.cc27wb2k
_database_code_depnum_ccdc_archive 'CCDC 2081838'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/d1qo00626f 2021
loop_
_audit_author_name
_audit_author_address
'Da-Ming Du'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2021-05-04 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
(2R,3'R,4'S)-3'-(3,4-dimethoxyphenyl)-1''-phenyl-5'-thioxodispiro[indene-2,2'-pyrrolidine-4',3''-pyrrolidine]-1,4'',5''(3H)-trione
_chemical_name_common            ?
_chemical_melting_point          425-427
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H24 N2 O5 S'
_chemical_formula_weight         512.56

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   11.359(3)
_cell_length_b                   12.150(3)
_cell_length_c                   19.406(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.359(7)
_cell_angle_gamma                90
_cell_volume                     2670.5(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4317
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      24.64

_exptl_crystal_description       cuboid
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.162
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19373
_diffrn_reflns_av_unetI/netI     0.0917
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.052
_diffrn_reflns_theta_max         24.841
_diffrn_reflns_theta_full        24.841
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             8999
_reflns_number_gt                5780
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_max     0.957
_reflns_Friedel_fraction_full    0.957

_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.1020P)²] 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 2013 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8999
_refine_ls_number_parameters     667
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0674
_refine_ls_wR_factor_ref         0.1800
_refine_ls_wR_factor_gt          0.1654
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_restrained_S_all      0.966
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.6906(2) 0.0951(2) 0.03825(11) 0.0601(6) Uani 1 1 d . . . . .
S2 S -0.1093(2) 0.7164(2) 0.30679(12) 0.0679(7) Uani 1 1 d . . . . .
O7 O 0.2532(4) 0.6181(4) 0.7539(2) 0.0446(13) Uani 1 1 d . . . . .
O1 O 0.2081(5) 0.4751(4) 0.2884(2) 0.0500(14) Uani 1 1 d . . . . .
O9 O 0.0015(5) 0.5014(4) 0.4453(3) 0.0528(14) Uani 1 1 d . . . . .
O3 O 0.6592(5) 0.4253(4) -0.0525(2) 0.0476(13) Uani 1 1 d . . . . .
O4 O 0.4501(5) 0.3264(5) -0.0060(3) 0.0533(14) Uani 1 1 d . . . . .
O10 O -0.2460(5) 0.5057(4) 0.4705(3) 0.0574(15) Uani 1 1 d . . . . .
O2 O 0.2381(5) 0.6560(4) 0.2236(3) 0.0579(16) Uani 1 1 d . . . . .
N1 N 0.7373(5) 0.3760(5) 0.0574(3) 0.0362(14) Uani 1 1 d . . . . .
O5 O 0.4477(5) 0.0775(5) 0.2453(3) 0.0605(16) Uani 1 1 d . . . . .
O6 O 0.2197(6) 0.8213(4) 0.7197(3) 0.0668(18) Uani 1 1 d . . . . .
N2 N 0.4880(5) 0.1051(5) 0.0986(3) 0.0400(14) Uani 1 1 d . . . . .
H2A H 0.470981 0.037642 0.088982 0.048 Uiso 1 1 calc R U . . .
N4 N -0.2055(5) 0.6922(5) 0.4858(3) 0.0400(15) Uani 1 1 d . . . . .
O8 O 0.2249(6) 0.9051(5) 0.3923(3) 0.0612(16) Uani 1 1 d . . . . .
N3 N 0.1128(5) 0.6896(5) 0.3575(3) 0.0406(15) Uani 1 1 d . . . . .
H3A H 0.135345 0.668543 0.318361 0.049 Uiso 1 1 calc R U . . .
C33 C 0.1999(6) 0.7478(5) 0.6670(3) 0.0327(16) Uani 1 1 d . . . . .
C22 C 0.3761(7) 0.1117(7) 0.2011(4) 0.0458(19) Uani 1 1 d . . . . .
C50 C -0.1795(7) 0.5870(6) 0.4716(3) 0.0408(17) Uani 1 1 d . . . . .
C13 C 0.5461(7) 0.3272(6) 0.0292(4) 0.0394(18) Uani 1 1 d . . . . .
C10 C 0.5798(6) 0.2752(6) 0.0988(3) 0.0318(16) Uani 1 1 d . . . . .
C35 C 0.1490(6) 0.6970(6) 0.5480(3) 0.0335(16) Uani 1 1 d . . . . .
C32 C 0.2208(6) 0.6362(6) 0.6852(3) 0.0387(18) Uani 1 1 d . . . . .
C34 C 0.1681(6) 0.7727(6) 0.5998(4) 0.0379(17) Uani 1 1 d . . . . .
H34A H 0.158603 0.846653 0.588269 0.046 Uiso 1 1 calc R U . . .
C51 C -0.3117(6) 0.7289(6) 0.5118(4) 0.0394(18) Uani 1 1 d . . . . .
C48 C -0.0520(7) 0.5841(6) 0.4541(3) 0.0394(17) Uani 1 1 d . . . . .
C24 C 0.2478(6) 0.1083(6) 0.1996(4) 0.0462(19) Uani 1 1 d . . . . .
C12 C 0.6542(6) 0.3836(6) 0.0045(3) 0.0347(17) Uani 1 1 d . . . . .
C46 C 0.1167(6) 0.7350(6) 0.4758(3) 0.0355(16) Uani 1 1 d . . . . .
H46A H 0.115618 0.815535 0.478921 0.043 Uiso 1 1 calc R U . . .
C21 C 0.4098(6) 0.1733(6) 0.1361(4) 0.0383(17) Uani 1 1 d . . . . .
C3 C 0.2898(7) 0.4710(7) 0.2407(3) 0.0424(18) Uani 1 1 d . . . . .
C38 C 0.1978(6) 0.7095(6) 0.4165(3) 0.0368(16) Uani 1 1 d . . . . .
C57 C -0.0001(6) 0.7053(6) 0.3666(3) 0.0348(16) Uani 1 1 d . . . . .
C36 C 0.1693(7) 0.5869(6) 0.5672(3) 0.0453(19) Uani 1 1 d . . . . .
H36A H 0.158385 0.532058 0.533895 0.054 Uiso 1 1 calc R U . . .
C41 C 0.3744(7) 0.7744(6) 0.3677(4) 0.0409(18) Uani 1 1 d . . . . .
C4 C 0.3047(7) 0.5717(6) 0.2035(3) 0.0404(18) Uani 1 1 d . . . . .
C6 C 0.4432(7) 0.4786(6) 0.1371(4) 0.0449(19) Uani 1 1 d . . . . .
H6A H 0.494951 0.482084 0.102283 0.054 Uiso 1 1 calc R U . . .
C7 C 0.3522(7) 0.3792(6) 0.2241(4) 0.0403(18) Uani 1 1 d . . . . .
H7A H 0.343843 0.314501 0.248857 0.048 Uiso 1 1 calc R U . . .
C37 C 0.2046(7) 0.5582(6) 0.6339(3) 0.0401(18) Uani 1 1 d . . . . .
H37A H 0.218054 0.484477 0.644741 0.048 Uiso 1 1 calc R U . . .
C39 C 0.2927(6) 0.6196(6) 0.4262(4) 0.0422(18) Uani 1 1 d . . . . .
H39A H 0.320065 0.611548 0.474498 0.051 Uiso 1 1 calc R U . . .
H39B H 0.262997 0.549306 0.408680 0.051 Uiso 1 1 calc R U . . .
C9 C 0.4906(7) 0.2732(6) 0.1545(3) 0.0385(17) Uani 1 1 d . . . . .
H9A H 0.536401 0.252896 0.197392 0.046 Uiso 1 1 calc R U . . .
C58 C 0.2649(7) 0.8118(7) 0.3933(4) 0.0420(19) Uani 1 1 d . . . . .
C23 C 0.2903(6) 0.1986(7) 0.0950(4) 0.0447(19) Uani 1 1 d . . . . .
H23A H 0.280791 0.277165 0.087495 0.054 Uiso 1 1 calc R U . . .
H23B H 0.285306 0.161700 0.050548 0.054 Uiso 1 1 calc R U . . .
C8 C 0.4279(7) 0.3811(6) 0.1707(3) 0.0370(17) Uani 1 1 d . . . . .
C25 C 0.1981(7) 0.1553(7) 0.1398(4) 0.049(2) Uani 1 1 d . . . . .
C40 C 0.3907(7) 0.6626(7) 0.3839(4) 0.048(2) Uani 1 1 d . . . . .
C5 C 0.3824(7) 0.5723(7) 0.1546(4) 0.049(2) Uani 1 1 d . . . . .
H5A H 0.395773 0.637856 0.131746 0.058 Uiso 1 1 calc R U . . .
C14 C 0.8597(7) 0.4140(7) 0.0594(4) 0.0447(19) Uani 1 1 d . . . . .
C52 C -0.3589(7) 0.8306(7) 0.4904(4) 0.054(2) Uani 1 1 d . . . . .
H52A H -0.321134 0.875077 0.459871 0.065 Uiso 1 1 calc R U . . .
C45 C 0.4873(8) 0.6076(9) 0.3631(4) 0.063(2) Uani 1 1 d . . . . .
H45A H 0.499443 0.533999 0.374722 0.076 Uiso 1 1 calc R U . . .
C31 C 0.2771(9) 0.5060(7) 0.7719(4) 0.057(2) Uani 1 1 d . . . . .
H31A H 0.298952 0.500787 0.820562 0.085 Uiso 1 1 calc R U . . .
H31B H 0.207712 0.462467 0.760695 0.085 Uiso 1 1 calc R U . . .
H31C H 0.340568 0.479299 0.746553 0.085 Uiso 1 1 calc R U . . .
C11 C 0.6979(6) 0.3240(6) 0.1193(3) 0.0378(17) Uani 1 1 d . . . . .
H11A H 0.691817 0.378004 0.155711 0.045 Uiso 1 1 calc R U . . .
H11B H 0.753054 0.267222 0.135868 0.045 Uiso 1 1 calc R U . . .
C20 C 0.5885(7) 0.1512(6) 0.0795(3) 0.0403(18) Uani 1 1 d . . . . .
C47 C -0.0124(6) 0.7027(6) 0.4435(4) 0.0388(17) Uani 1 1 d . . . . .
C49 C -0.1115(6) 0.7717(6) 0.4696(4) 0.0440(19) Uani 1 1 d . . . . .
H49A H -0.083676 0.812524 0.510598 0.053 Uiso 1 1 calc R U . . .
H49B H -0.141288 0.823506 0.434395 0.053 Uiso 1 1 calc R U . . .
C29 C 0.1775(8) 0.0650(8) 0.2497(5) 0.061(2) Uani 1 1 d . . . . .
H29A H 0.210398 0.031329 0.289674 0.073 Uiso 1 1 calc R U . . .
C26 C 0.0781(7) 0.1644(9) 0.1281(5) 0.069(3) Uani 1 1 d . . . . .
H26A H 0.044430 0.197638 0.088175 0.083 Uiso 1 1 calc R U . . .
C15 C 0.9110(8) 0.4360(8) -0.0027(5) 0.064(2) Uani 1 1 d . . . . .
H15A H 0.869027 0.426210 -0.045317 0.076 Uiso 1 1 calc R U . . .
C56 C -0.3680(8) 0.6664(7) 0.5590(5) 0.060(2) Uani 1 1 d . . . . .
H56A H -0.335818 0.599389 0.574050 0.072 Uiso 1 1 calc R U . . .
C2 C 0.1751(9) 0.3741(7) 0.3175(5) 0.070(3) Uani 1 1 d . . . . .
H2B H 0.117362 0.387457 0.350160 0.105 Uiso 1 1 calc R U . . .
H2C H 0.142043 0.326590 0.281500 0.105 Uiso 1 1 calc R U . . .
H2D H 0.243286 0.339803 0.340463 0.105 Uiso 1 1 calc R U . . .
C53 C -0.4646(9) 0.8631(9) 0.5163(5) 0.072(3) Uani 1 1 d . . . . .
H53A H -0.500237 0.928745 0.501388 0.087 Uiso 1 1 calc R U . . .
C42 C 0.4565(8) 0.8307(8) 0.3320(5) 0.061(2) Uani 1 1 d . . . . .
H42A H 0.447582 0.905424 0.322527 0.073 Uiso 1 1 calc R U . . .
C54 C -0.5172(9) 0.7982(10) 0.5643(6) 0.077(3) Uani 1 1 d . . . . .
H54A H -0.585739 0.822311 0.582873 0.092 Uiso 1 1 calc R U . . .
C1 C 0.2425(10) 0.7573(8) 0.1856(5) 0.075(3) Uani 1 1 d . . . . .
H1A H 0.191729 0.810549 0.204726 0.113 Uiso 1 1 calc R U . . .
H1B H 0.322018 0.784606 0.188627 0.113 Uiso 1 1 calc R U . . .
H1C H 0.216630 0.744351 0.138034 0.113 Uiso 1 1 calc R U . . .
C43 C 0.5520(8) 0.7727(9) 0.3109(6) 0.076(3) Uani 1 1 d . . . . .
H43A H 0.608226 0.808732 0.286682 0.091 Uiso 1 1 calc R U . . .
C28 C 0.0563(10) 0.0752(11) 0.2362(7) 0.101(4) Uani 1 1 d . . . . .
H28A H 0.007152 0.048543 0.268572 0.121 Uiso 1 1 calc R U . . .
C27 C 0.0072(9) 0.1220(11) 0.1783(6) 0.089(4) Uani 1 1 d . . . . .
H27A H -0.074528 0.126422 0.171284 0.107 Uiso 1 1 calc R U . . .
C16 C 1.0254(8) 0.4725(10) 0.0019(6) 0.083(3) Uani 1 1 d . . . . .
H16A H 1.060788 0.491109 -0.038223 0.099 Uiso 1 1 calc R U . . .
C44 C 0.5650(9) 0.6614(9) 0.3253(5) 0.077(3) Uani 1 1 d . . . . .
H44A H 0.627985 0.622999 0.308914 0.093 Uiso 1 1 calc R U . . .
C55 C -0.4707(9) 0.7026(10) 0.5837(5) 0.073(3) Uani 1 1 d . . . . .
H55A H -0.508469 0.659046 0.614669 0.087 Uiso 1 1 calc R U . . .
C19 C 0.9202(8) 0.4278(9) 0.1209(4) 0.070(3) Uani 1 1 d . . . . .
H19A H 0.883803 0.415144 0.161544 0.084 Uiso 1 1 calc R U . . .
C17 C 1.0888(9) 0.4820(12) 0.0648(6) 0.095(4) Uani 1 1 d . . . . .
H17A H 1.167615 0.503119 0.066565 0.113 Uiso 1 1 calc R U . . .
C18 C 1.0380(8) 0.4611(11) 0.1237(5) 0.089(4) Uani 1 1 d . . . . .
H18A H 1.081175 0.468720 0.166060 0.107 Uiso 1 1 calc R U . . .
C30 C 0.2103(14) 0.9333(8) 0.7011(5) 0.107(5) Uani 1 1 d . . . . .
H30A H 0.225678 0.978184 0.741532 0.161 Uiso 1 1 calc R U . . .
H30B H 0.266706 0.950070 0.668240 0.161 Uiso 1 1 calc R U . . .
H30C H 0.132075 0.947949 0.680950 0.161 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C20 1.610(8) . ?
S2 C57 1.638(7) . ?
O7 C32 1.375(8) . ?
O7 C31 1.427(9) . ?
O1 C3 1.361(8) . ?
O1 C2 1.412(10) . ?
O9 C48 1.193(9) . ?
O3 C12 1.222(7) . ?
O4 C13 1.242(8) . ?
O10 C50 1.243(9) . ?
O2 C4 1.348(8) . ?
O2 C1 1.438(11) . ?
N1 C12 1.342(9) . ?
N1 C11 1.459(8) . ?
N1 C14 1.463(9) . ?
O5 C22 1.210(9) . ?
O6 C33 1.364(8) . ?
O6 C30 1.410(11) . ?
N2 C20 1.348(9) . ?
N2 C21 1.450(9) . ?
N2 H2A 0.8600 . ?
N4 C50 1.345(9) . ?
N4 C51 1.414(9) . ?
N4 C49 1.491(9) . ?
O8 C58 1.221(9) . ?
N3 C57 1.321(9) . ?
N3 C38 1.460(9) . ?
N3 H3A 0.8600 . ?
C33 C34 1.359(9) . ?
C33 C32 1.417(10) . ?
C22 C24 1.456(10) . ?
C22 C21 1.541(10) . ?
C50 C48 1.514(10) . ?
C13 C10 1.514(10) . ?
C13 C12 1.516(10) . ?
C10 C11 1.492(10) . ?
C10 C9 1.536(9) . ?
C10 C20 1.557(10) . ?
C35 C34 1.368(9) . ?
C35 C36 1.403(10) . ?
C35 C46 1.494(9) . ?
C32 C37 1.376(10) . ?
C34 H34A 0.9300 . ?
C51 C56 1.384(11) . ?
C51 C52 1.398(11) . ?
C48 C47 1.527(10) . ?
C24 C25 1.375(11) . ?
C24 C29 1.407(11) . ?
C46 C38 1.560(9) . ?
C46 C47 1.599(10) . ?
C46 H46A 0.9800 . ?
C21 C9 1.547(11) . ?
C21 C23 1.552(11) . ?
C3 C7 1.373(10) . ?
C3 C4 1.436(11) . ?
C38 C39 1.536(10) . ?
C38 C58 1.543(10) . ?
C57 C47 1.511(9) . ?
C36 C37 1.371(10) . ?
C36 H36A 0.9300 . ?
C41 C42 1.383(11) . ?
C41 C40 1.404(11) . ?
C41 C58 1.448(11) . ?
C4 C5 1.344(10) . ?
C6 C8 1.370(10) . ?
C6 C5 1.388(11) . ?
C6 H6A 0.9300 . ?
C7 C8 1.396(9) . ?
C7 H7A 0.9300 . ?
C37 H37A 0.9300 . ?
C39 C40 1.526(10) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C9 C8 1.536(10) . ?
C9 H9A 0.9800 . ?
C23 C25 1.507(10) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C25 C26 1.369(11) . ?
C40 C45 1.371(12) . ?
C5 H5A 0.9300 . ?
C14 C19 1.342(11) . ?
C14 C15 1.405(10) . ?
C52 C53 1.394(12) . ?
C52 H52A 0.9300 . ?
C45 C44 1.357(12) . ?
C45 H45A 0.9300 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C47 C49 1.521(10) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C29 C28 1.386(15) . ?
C29 H29A 0.9300 . ?
C26 C27 1.408(13) . ?
C26 H26A 0.9300 . ?
C15 C16 1.369(12) . ?
C15 H15A 0.9300 . ?
C56 C55 1.367(13) . ?
C56 H56A 0.9300 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2 H2D 0.9600 . ?
C53 C54 1.390(15) . ?
C53 H53A 0.9300 . ?
C42 C43 1.382(13) . ?
C42 H42A 0.9300 . ?
C54 C55 1.319(15) . ?
C54 H54A 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C43 C44 1.387(14) . ?
C43 H43A 0.9300 . ?
C28 C27 1.342(15) . ?
C28 H28A 0.9300 . ?
C27 H27A 0.9300 . ?
C16 C17 1.374(14) . ?
C16 H16A 0.9300 . ?
C44 H44A 0.9300 . ?
C55 H55A 0.9300 . ?
C19 C18 1.395(12) . ?
C19 H19A 0.9300 . ?
C17 C18 1.343(13) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

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
C32 O7 C31 114.9(6) . . ?
C3 O1 C2 117.1(6) . . ?
C4 O2 C1 117.4(6) . . ?
C12 N1 C11 114.7(6) . . ?
C12 N1 C14 127.6(6) . . ?
C11 N1 C14 117.7(5) . . ?
C33 O6 C30 115.7(6) . . ?
C20 N2 C21 117.7(6) . . ?
C20 N2 H2A 121.2 . . ?
C21 N2 H2A 121.2 . . ?
C50 N4 C51 125.3(6) . . ?
C50 N4 C49 113.7(6) . . ?
C51 N4 C49 121.0(6) . . ?
C57 N3 C38 117.6(5) . . ?
C57 N3 H3A 121.2 . . ?
C38 N3 H3A 121.2 . . ?
C34 C33 O6 126.2(6) . . ?
C34 C33 C32 118.6(6) . . ?
O6 C33 C32 115.1(6) . . ?
O5 C22 C24 128.4(7) . . ?
O5 C22 C21 123.5(7) . . ?
C24 C22 C21 107.9(7) . . ?
O10 C50 N4 128.1(7) . . ?
O10 C50 C48 124.6(7) . . ?
N4 C50 C48 107.2(6) . . ?
O4 C13 C10 129.8(7) . . ?
O4 C13 C12 121.9(6) . . ?
C10 C13 C12 108.3(6) . . ?
C11 C10 C13 103.5(6) . . ?
C11 C10 C9 116.5(6) . . ?
C13 C10 C9 119.8(6) . . ?
C11 C10 C20 112.1(6) . . ?
C13 C10 C20 101.8(5) . . ?
C9 C10 C20 102.2(5) . . ?
C34 C35 C36 115.6(6) . . ?
C34 C35 C46 119.7(6) . . ?
C36 C35 C46 124.6(6) . . ?
O7 C32 C37 127.1(7) . . ?
O7 C32 C33 115.0(6) . . ?
C37 C32 C33 117.9(6) . . ?
C33 C34 C35 124.8(7) . . ?
C33 C34 H34A 117.6 . . ?
C35 C34 H34A 117.6 . . ?
C56 C51 C52 119.7(7) . . ?
C56 C51 N4 120.9(7) . . ?
C52 C51 N4 119.4(6) . . ?
O9 C48 C50 123.9(7) . . ?
O9 C48 C47 128.1(7) . . ?
C50 C48 C47 107.7(6) . . ?
C25 C24 C29 121.3(8) . . ?
C25 C24 C22 110.6(7) . . ?
C29 C24 C22 128.1(8) . . ?
O3 C12 N1 129.9(7) . . ?
O3 C12 C13 124.6(6) . . ?
N1 C12 C13 105.5(6) . . ?
C35 C46 C38 120.9(6) . . ?
C35 C46 C47 116.4(6) . . ?
C38 C46 C47 103.7(5) . . ?
C35 C46 H46A 104.7 . . ?
C38 C46 H46A 104.7 . . ?
C47 C46 H46A 104.7 . . ?
N2 C21 C22 109.4(6) . . ?
N2 C21 C9 100.9(5) . . ?
C22 C21 C9 111.9(6) . . ?
N2 C21 C23 113.7(6) . . ?
C22 C21 C23 104.8(6) . . ?
C9 C21 C23 116.3(6) . . ?
O1 C3 C7 125.4(7) . . ?
O1 C3 C4 115.0(6) . . ?
C7 C3 C4 119.5(6) . . ?
N3 C38 C39 113.3(6) . . ?
N3 C38 C58 102.5(5) . . ?
C39 C38 C58 104.6(6) . . ?
N3 C38 C46 102.6(6) . . ?
C39 C38 C46 119.9(6) . . ?
C58 C38 C46 112.8(6) . . ?
N3 C57 C47 106.9(6) . . ?
N3 C57 S2 127.5(5) . . ?
C47 C57 S2 125.4(5) . . ?
C37 C36 C35 121.6(6) . . ?
C37 C36 H36A 119.2 . . ?
C35 C36 H36A 119.2 . . ?
C42 C41 C40 120.6(8) . . ?
C42 C41 C58 130.2(8) . . ?
C40 C41 C58 109.2(6) . . ?
C5 C4 O2 127.8(7) . . ?
C5 C4 C3 117.9(7) . . ?
O2 C4 C3 114.3(6) . . ?
C8 C6 C5 120.6(6) . . ?
C8 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C3 C7 C8 121.2(7) . . ?
C3 C7 H7A 119.4 . . ?
C8 C7 H7A 119.4 . . ?
C36 C37 C32 121.4(7) . . ?
C36 C37 H37A 119.3 . . ?
C32 C37 H37A 119.3 . . ?
C40 C39 C38 103.0(6) . . ?
C40 C39 H39A 111.2 . . ?
C38 C39 H39A 111.2 . . ?
C40 C39 H39B 111.2 . . ?
C38 C39 H39B 111.2 . . ?
H39A C39 H39B 109.1 . . ?
C8 C9 C10 118.2(6) . . ?
C8 C9 C21 116.1(6) . . ?
C10 C9 C21 105.2(5) . . ?
C8 C9 H9A 105.4 . . ?
C10 C9 H9A 105.4 . . ?
C21 C9 H9A 105.4 . . ?
O8 C58 C41 127.9(7) . . ?
O8 C58 C38 124.2(7) . . ?
C41 C58 C38 107.7(7) . . ?
C25 C23 C21 104.7(6) . . ?
C25 C23 H23A 110.8 . . ?
C21 C23 H23A 110.8 . . ?
C25 C23 H23B 110.8 . . ?
C21 C23 H23B 110.8 . . ?
H23A C23 H23B 108.9 . . ?
C6 C8 C7 118.4(7) . . ?
C6 C8 C9 124.3(6) . . ?
C7 C8 C9 117.4(6) . . ?
C26 C25 C24 120.9(7) . . ?
C26 C25 C23 127.1(8) . . ?
C24 C25 C23 111.9(7) . . ?
C45 C40 C41 120.0(7) . . ?
C45 C40 C39 128.7(8) . . ?
C41 C40 C39 111.2(7) . . ?
C4 C5 C6 122.3(7) . . ?
C4 C5 H5A 118.9 . . ?
C6 C5 H5A 118.9 . . ?
C19 C14 C15 121.5(8) . . ?
C19 C14 N1 119.0(6) . . ?
C15 C14 N1 119.5(7) . . ?
C53 C52 C51 117.7(9) . . ?
C53 C52 H52A 121.1 . . ?
C51 C52 H52A 121.1 . . ?
C44 C45 C40 119.5(9) . . ?
C44 C45 H45A 120.3 . . ?
C40 C45 H45A 120.3 . . ?
O7 C31 H31A 109.5 . . ?
O7 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O7 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N1 C11 C10 106.1(5) . . ?
N1 C11 H11A 110.5 . . ?
C10 C11 H11A 110.5 . . ?
N1 C11 H11B 110.5 . . ?
C10 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
N2 C20 C10 105.4(6) . . ?
N2 C20 S1 128.2(6) . . ?
C10 C20 S1 126.2(6) . . ?
C57 C47 C49 116.3(6) . . ?
C57 C47 C48 101.7(5) . . ?
C49 C47 C48 104.1(6) . . ?
C57 C47 C46 103.4(5) . . ?
C49 C47 C46 114.4(6) . . ?
C48 C47 C46 116.7(6) . . ?
N4 C49 C47 105.8(6) . . ?
N4 C49 H49A 110.6 . . ?
C47 C49 H49A 110.6 . . ?
N4 C49 H49B 110.6 . . ?
C47 C49 H49B 110.6 . . ?
H49A C49 H49B 108.7 . . ?
C28 C29 C24 116.3(9) . . ?
C28 C29 H29A 121.8 . . ?
C24 C29 H29A 121.8 . . ?
C25 C26 C27 118.0(9) . . ?
C25 C26 H26A 121.0 . . ?
C27 C26 H26A 121.0 . . ?
C16 C15 C14 117.4(8) . . ?
C16 C15 H15A 121.3 . . ?
C14 C15 H15A 121.3 . . ?
C55 C56 C51 120.3(10) . . ?
C55 C56 H56A 119.8 . . ?
C51 C56 H56A 119.8 . . ?
O1 C2 H2B 109.5 . . ?
O1 C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O1 C2 H2D 109.5 . . ?
H2B C2 H2D 109.5 . . ?
H2C C2 H2D 109.5 . . ?
C54 C53 C52 120.4(10) . . ?
C54 C53 H53A 119.8 . . ?
C52 C53 H53A 119.8 . . ?
C43 C42 C41 118.0(8) . . ?
C43 C42 H42A 121.0 . . ?
C41 C42 H42A 121.0 . . ?
C55 C54 C53 120.5(9) . . ?
C55 C54 H54A 119.7 . . ?
C53 C54 H54A 119.7 . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C42 C43 C44 120.7(8) . . ?
C42 C43 H43A 119.6 . . ?
C44 C43 H43A 119.6 . . ?
C27 C28 C29 122.6(8) . . ?
C27 C28 H28A 118.7 . . ?
C29 C28 H28A 118.7 . . ?
C28 C27 C26 120.7(9) . . ?
C28 C27 H27A 119.6 . . ?
C26 C27 H27A 119.6 . . ?
C15 C16 C17 121.0(8) . . ?
C15 C16 H16A 119.5 . . ?
C17 C16 H16A 119.5 . . ?
C45 C44 C43 121.0(9) . . ?
C45 C44 H44A 119.5 . . ?
C43 C44 H44A 119.5 . . ?
C54 C55 C56 121.2(10) . . ?
C54 C55 H55A 119.4 . . ?
C56 C55 H55A 119.4 . . ?
C14 C19 C18 119.7(8) . . ?
C14 C19 H19A 120.2 . . ?
C18 C19 H19A 120.2 . . ?
C18 C17 C16 120.7(9) . . ?
C18 C17 H17A 119.6 . . ?
C16 C17 H17A 119.6 . . ?
C17 C18 C19 119.7(9) . . ?
C17 C18 H18A 120.2 . . ?
C19 C18 H18A 120.2 . . ?
O6 C30 H30A 109.5 . . ?
O6 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O6 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C15 H15A O3 0.93 2.38 2.952(11) 119.8 . yes
C49 H49A O9 0.97 2.60 3.429(10) 143.9 2_556 yes
C11 H11A O6 0.97 2.64 3.191(8) 116.5 2_646 yes
C31 H31A S1 0.96 2.96 3.831(9) 150.8 2_656 yes
C39 H39B O1 0.97 2.54 3.281(10) 133.6 . yes
C46 H46A O8 0.98 2.42 2.952(9) 113.4 . yes
C34 H34A O10 0.93 2.49 3.293(9) 144.8 2_556 yes
N3 H3A O2 0.86 2.26 3.084(8) 161.5 . yes
N3 H3A O1 0.86 2.57 3.161(8) 126.5 . yes
N2 H2A O3 0.86 2.10 2.854(8) 146.7 2_645 yes



loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.220 0.242 0.878 150 44 ' '
2 -0.220 0.742 0.122 151 44 ' '
3 0.081 0.138 0.385 12 1 ' '
4 0.919 0.638 0.615 11 1 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?


_refine_diff_density_max         0.417
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.060


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Petroleum ether-ethyl acetate'
