# Electronic Supplementary Material (ESI) for Soft Matter.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_450
_database_code_depnum_ccdc_archive 'CCDC 1583446'
_audit_update_record             
;
2017-11-01 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H50 N4 O8 S'
_chemical_formula_weight         578.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   10.2919(8)
_cell_length_b                   15.7509(9)
_cell_length_c                   20.9127(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3390.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6919
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      21.4

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.142
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37722
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.205
_diffrn_reflns_theta_max         25.450
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6256
_reflns_number_gt                3394
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    1.000

_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0767P)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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0061(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1195 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6256
_refine_ls_number_parameters     456
_refine_ls_number_restraints     267
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1417
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.992
_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
C1 C 0.3130(5) -0.0224(2) 0.2867(2) 0.0611(13) Uani 1 1 d . . . . .
H1 H 0.3779 -0.0673 0.2926 0.073 Uiso 1 1 calc R U . . .
C2 C 0.1866(5) -0.0528(3) 0.3165(2) 0.0785(14) Uani 1 1 d . . . . .
H2 H 0.1578 -0.1023 0.2920 0.094 Uiso 1 1 calc R U . . .
C3 C 0.2093(7) -0.0825(4) 0.3850(3) 0.106(2) Uani 1 1 d . . . . .
H3A H 0.2363 -0.0352 0.4107 0.158 Uiso 1 1 calc R U . . .
H3B H 0.2756 -0.1253 0.3854 0.158 Uiso 1 1 calc R U . . .
H3C H 0.1301 -0.1056 0.4019 0.158 Uiso 1 1 calc R U . . .
C4 C 0.0827(6) 0.0112(4) 0.3122(3) 0.0994(19) Uani 1 1 d . . . . .
H4A H 0.0820 0.0339 0.2691 0.119 Uiso 1 1 calc R U . . .
H4B H 0.1039 0.0576 0.3409 0.119 Uiso 1 1 calc R U . . .
C5 C -0.0538(7) -0.0200(6) 0.3281(4) 0.151(3) Uani 1 1 d . . . . .
H5A H -0.0799 -0.0619 0.2974 0.227 Uiso 1 1 calc R U . . .
H5B H -0.1132 0.0269 0.3269 0.227 Uiso 1 1 calc R U . . .
H5C H -0.0541 -0.0447 0.3701 0.227 Uiso 1 1 calc R U . . .
C6 C 0.3005(5) -0.0067(3) 0.2166(2) 0.0599(12) Uani 1 1 d . . . . .
C7 C 0.2783(8) -0.0709(3) 0.1120(3) 0.095(2) Uani 1 1 d D . . . .
H7 H 0.3188 -0.0192 0.0952 0.115 Uiso 1 1 calc R U . A 1
C8 C 0.3207(17) -0.1456(11) 0.0701(8) 0.130(5) Uani 0.572(12) 1 d D U P B 1
H8A H 0.2703 -0.1468 0.0310 0.156 Uiso 0.572(12) 1 calc R U P B 1
H8B H 0.3074 -0.1988 0.0926 0.156 Uiso 0.572(12) 1 calc R U P B 1
C9 C 0.4657(16) -0.1335(8) 0.0548(8) 0.138(4) Uani 0.572(12) 1 d D U P B 1
H9 H 0.5145 -0.1328 0.0950 0.165 Uiso 0.572(12) 1 calc R U P B 1
C10 C 0.512(2) -0.2105(11) 0.0143(7) 0.151(5) Uani 0.572(12) 1 d D U P B 1
H10A H 0.4872 -0.2623 0.0352 0.226 Uiso 0.572(12) 1 calc R U P B 1
H10B H 0.6048 -0.2087 0.0099 0.226 Uiso 0.572(12) 1 calc R U P B 1
H10C H 0.4725 -0.2081 -0.0273 0.226 Uiso 0.572(12) 1 calc R U P B 1
C11 C 0.498(2) -0.0515(11) 0.0167(8) 0.158(6) Uani 0.572(12) 1 d D U P B 1
H11A H 0.4525 -0.0521 -0.0233 0.237 Uiso 0.572(12) 1 calc R U P B 1
H11B H 0.5900 -0.0490 0.0089 0.237 Uiso 0.572(12) 1 calc R U P B 1
H11C H 0.4720 -0.0027 0.0411 0.237 Uiso 0.572(12) 1 calc R U P B 1
C8' C 0.360(3) -0.1519(14) 0.0926(9) 0.131(5) Uani 0.428(12) 1 d D U P B 2
H8'1 H 0.4412 -0.1515 0.1165 0.158 Uiso 0.428(12) 1 calc R U P B 2
H8'2 H 0.3126 -0.2024 0.1051 0.158 Uiso 0.428(12) 1 calc R U P B 2
C9' C 0.392(3) -0.1578(12) 0.0225(8) 0.137(4) Uani 0.428(12) 1 d D U P B 2
H9' H 0.3101 -0.1469 -0.0002 0.165 Uiso 0.428(12) 1 calc R U P B 2
C10' C 0.432(3) -0.2489(13) 0.0049(12) 0.145(6) Uani 0.428(12) 1 d D U P B 2
H10D H 0.5109 -0.2633 0.0272 0.217 Uiso 0.428(12) 1 calc R U P B 2
H10E H 0.4468 -0.2525 -0.0403 0.217 Uiso 0.428(12) 1 calc R U P B 2
H10F H 0.3647 -0.2877 0.0170 0.217 Uiso 0.428(12) 1 calc R U P B 2
C11' C 0.488(3) -0.0940(16) -0.0021(11) 0.164(6) Uani 0.428(12) 1 d D U P B 2
H11D H 0.4492 -0.0385 -0.0015 0.245 Uiso 0.428(12) 1 calc R U P B 2
H11E H 0.5116 -0.1083 -0.0451 0.245 Uiso 0.428(12) 1 calc R U P B 2
H11F H 0.5636 -0.0944 0.0245 0.245 Uiso 0.428(12) 1 calc R U P B 2
C12 C 0.1350(11) -0.0661(4) 0.0992(3) 0.109(2) Uani 1 1 d . . . . .
C13 C -0.0227(14) -0.0272(7) 0.0236(4) 0.213(6) Uani 1 1 d . . . . .
H13A H -0.0271 -0.0026 -0.0184 0.320 Uiso 1 1 calc R U . . .
H13B H -0.0612 -0.0827 0.0229 0.320 Uiso 1 1 calc R U . . .
H13C H -0.0689 0.0081 0.0533 0.320 Uiso 1 1 calc R U . . .
C14 C 0.6679(5) 0.1328(2) 0.2431(3) 0.0648(13) Uani 1 1 d D . . . .
H14 H 0.7234 0.1450 0.2801 0.078 Uiso 1 1 calc R U . C 3
C15 C 0.759(2) 0.1095(16) 0.1894(10) 0.095(4) Uani 0.61(2) 1 d D U P D 3
H15 H 0.8062 0.0583 0.2021 0.114 Uiso 0.61(2) 1 calc R U P D 3
C16 C 0.686(2) 0.0900(15) 0.1287(12) 0.115(6) Uani 0.61(2) 1 d D U P D 3
H16A H 0.6186 0.0493 0.1375 0.173 Uiso 0.61(2) 1 calc R U P D 3
H16B H 0.7447 0.0671 0.0976 0.173 Uiso 0.61(2) 1 calc R U P D 3
H16C H 0.6475 0.1412 0.1124 0.173 Uiso 0.61(2) 1 calc R U P D 3
C17 C 0.8571(19) 0.1795(12) 0.1773(10) 0.110(4) Uani 0.61(2) 1 d D U P D 3
H17A H 0.9154 0.1601 0.1439 0.132 Uiso 0.61(2) 1 calc R U P D 3
H17B H 0.8106 0.2282 0.1606 0.132 Uiso 0.61(2) 1 calc R U P D 3
C18 C 0.9390(16) 0.2096(12) 0.2325(13) 0.146(6) Uani 0.61(2) 1 d D U P D 3
H18A H 0.8844 0.2362 0.2639 0.218 Uiso 0.61(2) 1 calc R U P D 3
H18B H 1.0020 0.2497 0.2174 0.218 Uiso 0.61(2) 1 calc R U P D 3
H18C H 0.9828 0.1620 0.2515 0.218 Uiso 0.61(2) 1 calc R U P D 3
C15' C 0.735(4) 0.106(2) 0.1809(15) 0.094(5) Uani 0.39(2) 1 d D U P D 4
H15' H 0.7913 0.0580 0.1923 0.113 Uiso 0.39(2) 1 calc R U P D 4
C16' C 0.638(3) 0.071(2) 0.1312(18) 0.100(7) Uani 0.39(2) 1 d D U P D 4
H16D H 0.5860 0.1167 0.1151 0.150 Uiso 0.39(2) 1 calc R U P D 4
H16E H 0.5835 0.0293 0.1510 0.150 Uiso 0.39(2) 1 calc R U P D 4
H16F H 0.6854 0.0453 0.0966 0.150 Uiso 0.39(2) 1 calc R U P D 4
C17' C 0.823(2) 0.1707(19) 0.1486(15) 0.103(5) Uani 0.39(2) 1 d D U P D 4
H17C H 0.8531 0.1479 0.1081 0.124 Uiso 0.39(2) 1 calc R U P D 4
H17D H 0.7736 0.2217 0.1397 0.124 Uiso 0.39(2) 1 calc R U P D 4
C18' C 0.939(2) 0.194(2) 0.1886(18) 0.130(7) Uani 0.39(2) 1 d D U P D 4
H18D H 0.9105 0.2238 0.2260 0.195 Uiso 0.39(2) 1 calc R U P D 4
H18E H 0.9964 0.2291 0.1643 0.195 Uiso 0.39(2) 1 calc R U P D 4
H18F H 0.9835 0.1429 0.2013 0.195 Uiso 0.39(2) 1 calc R U P D 4
C19 C 0.5887(5) 0.2124(3) 0.2316(2) 0.0581(12) Uani 1 1 d . . . . .
C20 C 0.3903(4) 0.2797(2) 0.1967(2) 0.0552(12) Uani 1 1 d . . . . .
H20 H 0.4455 0.3240 0.1782 0.066 Uiso 1 1 calc R U . . .
C21 C 0.2812(5) 0.2613(3) 0.1501(2) 0.0624(13) Uani 1 1 d . . . . .
H21A H 0.2262 0.2175 0.1683 0.075 Uiso 1 1 calc R U . . .
H21B H 0.2288 0.3121 0.1457 0.075 Uiso 1 1 calc R U . . .
C22 C 0.3225(6) 0.2333(4) 0.0849(3) 0.0895(17) Uani 1 1 d . . . . .
H22 H 0.3770 0.1828 0.0905 0.107 Uiso 1 1 calc R U . . .
C23 C 0.4014(10) 0.2968(6) 0.0511(3) 0.163(4) Uani 1 1 d . . . . .
H23A H 0.3530 0.3487 0.0473 0.245 Uiso 1 1 calc R U . . .
H23B H 0.4229 0.2761 0.0093 0.245 Uiso 1 1 calc R U . . .
H23C H 0.4798 0.3072 0.0747 0.245 Uiso 1 1 calc R U . . .
C24 C 0.2055(8) 0.2066(6) 0.0460(4) 0.148(3) Uani 1 1 d . . . . .
H24A H 0.1555 0.2559 0.0348 0.222 Uiso 1 1 calc R U . . .
H24B H 0.1528 0.1686 0.0707 0.222 Uiso 1 1 calc R U . . .
H24C H 0.2340 0.1785 0.0078 0.222 Uiso 1 1 calc R U . . .
C25 C 0.3330(5) 0.3134(3) 0.2582(2) 0.0597(13) Uani 1 1 d . . . . .
C26 C 0.2181(7) 0.2766(4) 0.3518(3) 0.114(2) Uani 1 1 d . . . . .
H26A H 0.2766 0.3081 0.3786 0.170 Uiso 1 1 calc R U . . .
H26B H 0.1894 0.2267 0.3740 0.170 Uiso 1 1 calc R U . . .
H26C H 0.1444 0.3113 0.3414 0.170 Uiso 1 1 calc R U . . .
N1 N 0.3609(4) 0.0542(2) 0.31963(17) 0.0589(10) Uani 1 1 d . . . . .
N2 N 0.3023(5) -0.0745(3) 0.1791(2) 0.0759(14) Uani 1 1 d . . . . .
N3 N 0.5857(4) 0.0610(3) 0.26196(18) 0.0597(10) Uani 1 1 d . . . . .
N4 N 0.4697(4) 0.2055(2) 0.20799(17) 0.0537(10) Uani 1 1 d . . . . .
O1 O 0.5529(4) -0.0159(2) 0.36283(16) 0.0810(10) Uani 1 1 d . . . . .
O2 O 0.5379(4) 0.14043(19) 0.36007(15) 0.0810(10) Uani 1 1 d . . . . .
O3 O 0.2878(3) 0.06515(18) 0.19398(15) 0.0713(9) Uani 1 1 d . . . . .
O4 O 0.0535(7) -0.0872(5) 0.1342(3) 0.191(3) Uani 1 1 d . . . . .
O5 O 0.1127(8) -0.0339(3) 0.0433(2) 0.150(2) Uani 1 1 d . . . . .
O6 O 0.6379(3) 0.28195(19) 0.24230(18) 0.0786(10) Uani 1 1 d . . . . .
O7 O 0.3258(4) 0.38600(19) 0.27313(18) 0.0915(12) Uani 1 1 d . . . . .
O8 O 0.2844(4) 0.25202(18) 0.29349(17) 0.0781(11) Uani 1 1 d . . . . .
S1 S 0.51614(13) 0.06038(7) 0.33145(5) 0.0656(4) Uani 1 1 d . . . . .
H1A H 0.338(5) 0.106(3) 0.302(2) 0.075(15) Uiso 1 1 d . . . . .
H2A H 0.311(4) -0.115(3) 0.192(2) 0.050(15) Uiso 1 1 d . . . . .
H3 H 0.619(5) 0.016(3) 0.256(2) 0.078(18) Uiso 1 1 d . . . . .
H4 H 0.433(4) 0.156(3) 0.204(2) 0.059(12) Uiso 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 N1 1.474(5) . ?
C1 C6 1.492(6) . ?
C1 C2 1.521(7) . ?
C1 H1 0.9800 . ?
C2 C4 1.471(8) . ?
C2 C3 1.525(7) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.525(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 O3 1.234(5) . ?
C6 N2 1.325(6) . ?
C7 N2 1.425(7) . ?
C7 C12 1.501(10) . ?
C7 C8 1.531(13) . ?
C7 C8' 1.584(16) . ?
C7 H7 0.9800 . ?
C8 C9 1.538(17) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.554(14) . ?
C9 C11 1.554(15) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C8' C9' 1.503(17) . ?
C8' H8'1 0.9700 . ?
C8' H8'2 0.9700 . ?
C9' C11' 1.501(18) . ?
C9' C10' 1.540(17) . ?
C9' H9' 0.9800 . ?
C10' H10D 0.9600 . ?
C10' H10E 0.9600 . ?
C10' H10F 0.9600 . ?
C11' H11D 0.9600 . ?
C11' H11E 0.9600 . ?
C11' H11F 0.9600 . ?
C12 O4 1.161(9) . ?
C12 O5 1.296(8) . ?
C13 O5 1.456(13) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N3 1.467(6) . ?
C14 C15 1.505(14) . ?
C14 C19 1.515(6) . ?
C14 C15' 1.533(19) . ?
C14 H14 0.9800 . ?
C15 C16 1.506(15) . ?
C15 C17 1.518(15) . ?
C15 H15 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.505(15) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C15' C17' 1.524(18) . ?
C15' C16' 1.539(19) . ?
C15' H15' 0.9800 . ?
C16' H16D 0.9600 . ?
C16' H16E 0.9600 . ?
C16' H16F 0.9600 . ?
C17' C18' 1.50(2) . ?
C17' H17C 0.9700 . ?
C17' H17D 0.9700 . ?
C18' H18D 0.9600 . ?
C18' H18E 0.9600 . ?
C18' H18F 0.9600 . ?
C19 O6 1.227(5) . ?
C19 N4 1.325(5) . ?
C20 N4 1.445(5) . ?
C20 C25 1.510(6) . ?
C20 C21 1.515(6) . ?
C20 H20 0.9800 . ?
C21 C22 1.495(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.470(9) . ?
C22 C24 1.512(9) . ?
C22 H22 0.9800 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O7 1.187(5) . ?
C25 O8 1.316(5) . ?
C26 O8 1.450(6) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
N1 S1 1.620(4) . ?
N1 H1A 0.93(5) . ?
N2 H2A 0.70(4) . ?
N3 S1 1.620(4) . ?
N3 H3 0.80(5) . ?
N4 H4 0.87(4) . ?
O1 S1 1.420(3) . ?
O2 S1 1.414(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C6 110.7(3) . . ?
N1 C1 C2 110.6(4) . . ?
C6 C1 C2 112.4(4) . . ?
N1 C1 H1 107.7 . . ?
C6 C1 H1 107.7 . . ?
C2 C1 H1 107.7 . . ?
C4 C2 C1 112.4(4) . . ?
C4 C2 C3 112.2(5) . . ?
C1 C2 C3 110.5(5) . . ?
C4 C2 H2 107.1 . . ?
C1 C2 H2 107.1 . . ?
C3 C2 H2 107.1 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 C5 115.8(5) . . ?
C2 C4 H4A 108.3 . . ?
C5 C4 H4A 108.3 . . ?
C2 C4 H4B 108.3 . . ?
C5 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O3 C6 N2 120.9(5) . . ?
O3 C6 C1 122.5(4) . . ?
N2 C6 C1 116.5(4) . . ?
N2 C7 C12 110.4(5) . . ?
N2 C7 C8 118.9(9) . . ?
C12 C7 C8 102.6(8) . . ?
N2 C7 C8' 97.3(9) . . ?
C12 C7 C8' 121.4(13) . . ?
N2 C7 H7 108.2 . . ?
C12 C7 H7 108.2 . . ?
C8 C7 H7 108.2 . . ?
C7 C8 C9 107.5(12) . . ?
C7 C8 H8A 110.2 . . ?
C9 C8 H8A 110.2 . . ?
C7 C8 H8B 110.2 . . ?
C9 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
C8 C9 C10 108.3(12) . . ?
C8 C9 C11 114.7(16) . . ?
C10 C9 C11 107.7(12) . . ?
C8 C9 H9 108.7 . . ?
C10 C9 H9 108.7 . . ?
C11 C9 H9 108.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9' C8' C7 114.4(15) . . ?
C9' C8' H8'1 108.7 . . ?
C7 C8' H8'1 108.7 . . ?
C9' C8' H8'2 108.7 . . ?
C7 C8' H8'2 108.7 . . ?
H8'1 C8' H8'2 107.6 . . ?
C11' C9' C8' 116(2) . . ?
C11' C9' C10' 111.3(17) . . ?
C8' C9' C10' 110.4(16) . . ?
C11' C9' H9' 106.3 . . ?
C8' C9' H9' 106.3 . . ?
C10' C9' H9' 106.3 . . ?
C9' C10' H10D 109.5 . . ?
C9' C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
C9' C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
C9' C11' H11D 109.5 . . ?
C9' C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
C9' C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
O4 C12 O5 123.6(10) . . ?
O4 C12 C7 125.6(7) . . ?
O5 C12 C7 110.8(8) . . ?
O5 C13 H13A 109.5 . . ?
O5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 111.8(10) . . ?
N3 C14 C19 111.7(4) . . ?
C15 C14 C19 114.7(12) . . ?
N3 C14 C15' 106.0(13) . . ?
C19 C14 C15' 109.7(18) . . ?
N3 C14 H14 106.0 . . ?
C15 C14 H14 106.0 . . ?
C19 C14 H14 106.0 . . ?
C14 C15 C16 111.7(18) . . ?
C14 C15 C17 111.2(14) . . ?
C16 C15 C17 109.8(15) . . ?
C14 C15 H15 108.0 . . ?
C16 C15 H15 108.0 . . ?
C17 C15 H15 108.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C15 118.3(14) . . ?
C18 C17 H17A 107.7 . . ?
C15 C17 H17A 107.7 . . ?
C18 C17 H17B 107.7 . . ?
C15 C17 H17B 107.7 . . ?
H17A C17 H17B 107.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17' C15' C14 117(2) . . ?
C17' C15' C16' 109(2) . . ?
C14 C15' C16' 112(2) . . ?
C17' C15' H15' 105.8 . . ?
C14 C15' H15' 105.8 . . ?
C16' C15' H15' 105.8 . . ?
C15' C16' H16D 109.5 . . ?
C15' C16' H16E 109.5 . . ?
H16D C16' H16E 109.5 . . ?
C15' C16' H16F 109.5 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 109.5 . . ?
C18' C17' C15' 113(2) . . ?
C18' C17' H17C 109.0 . . ?
C15' C17' H17C 109.0 . . ?
C18' C17' H17D 109.0 . . ?
C15' C17' H17D 109.0 . . ?
H17C C17' H17D 107.8 . . ?
C17' C18' H18D 109.5 . . ?
C17' C18' H18E 109.5 . . ?
H18D C18' H18E 109.5 . . ?
C17' C18' H18F 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 109.5 . . ?
O6 C19 N4 121.5(4) . . ?
O6 C19 C14 119.2(4) . . ?
N4 C19 C14 119.3(4) . . ?
N4 C20 C25 111.5(3) . . ?
N4 C20 C21 111.7(3) . . ?
C25 C20 C21 109.0(4) . . ?
N4 C20 H20 108.2 . . ?
C25 C20 H20 108.2 . . ?
C21 C20 H20 108.2 . . ?
C22 C21 C20 115.7(4) . . ?
C22 C21 H21A 108.4 . . ?
C20 C21 H21A 108.4 . . ?
C22 C21 H21B 108.4 . . ?
C20 C21 H21B 108.4 . . ?
H21A C21 H21B 107.4 . . ?
C23 C22 C21 113.2(5) . . ?
C23 C22 C24 111.7(6) . . ?
C21 C22 C24 110.2(5) . . ?
C23 C22 H22 107.1 . . ?
C21 C22 H22 107.1 . . ?
C24 C22 H22 107.1 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O7 C25 O8 122.4(4) . . ?
O7 C25 C20 126.0(4) . . ?
O8 C25 C20 111.5(3) . . ?
O8 C26 H26A 109.5 . . ?
O8 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O8 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C1 N1 S1 116.8(3) . . ?
C1 N1 H1A 117(3) . . ?
S1 N1 H1A 105(3) . . ?
C6 N2 C7 123.2(5) . . ?
C6 N2 H2A 121(4) . . ?
C7 N2 H2A 116(4) . . ?
C14 N3 S1 120.0(3) . . ?
C14 N3 H3 113(4) . . ?
S1 N3 H3 109(4) . . ?
C19 N4 C20 121.2(4) . . ?
C19 N4 H4 121(3) . . ?
C20 N4 H4 118(3) . . ?
C12 O5 C13 117.0(8) . . ?
C25 O8 C26 117.0(4) . . ?
O2 S1 O1 121.1(2) . . ?
O2 S1 N3 107.8(2) . . ?
O1 S1 N3 107.6(2) . . ?
O2 S1 N1 105.9(2) . . ?
O1 S1 N1 106.4(2) . . ?
N3 S1 N1 107.41(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C4 60.7(6) . . . . ?
C6 C1 C2 C4 -63.5(6) . . . . ?
N1 C1 C2 C3 -65.6(5) . . . . ?
C6 C1 C2 C3 170.2(4) . . . . ?
C1 C2 C4 C5 167.8(6) . . . . ?
C3 C2 C4 C5 -66.8(8) . . . . ?
N1 C1 C6 O3 -23.0(7) . . . . ?
C2 C1 C6 O3 101.1(5) . . . . ?
N1 C1 C6 N2 157.6(4) . . . . ?
C2 C1 C6 N2 -78.3(5) . . . . ?
N2 C7 C8 C9 -82.8(16) . . . . ?
C12 C7 C8 C9 155.1(13) . . . . ?
C7 C8 C9 C10 178.0(11) . . . . ?
C7 C8 C9 C11 -61.7(19) . . . . ?
N2 C7 C8' C9' -164(2) . . . . ?
C12 C7 C8' C9' 77(3) . . . . ?
C7 C8' C9' C11' 70(3) . . . . ?
C7 C8' C9' C10' -162(2) . . . . ?
N2 C7 C12 O4 -21.6(11) . . . . ?
C8 C7 C12 O4 106.1(12) . . . . ?
C8' C7 C12 O4 91.1(13) . . . . ?
N2 C7 C12 O5 157.8(5) . . . . ?
C8 C7 C12 O5 -74.5(10) . . . . ?
C8' C7 C12 O5 -89.5(11) . . . . ?
N3 C14 C15 C16 65.7(19) . . . . ?
C19 C14 C15 C16 -62.7(18) . . . . ?
N3 C14 C15 C17 -171.2(13) . . . . ?
C19 C14 C15 C17 60(2) . . . . ?
C14 C15 C17 C18 55(2) . . . . ?
C16 C15 C17 C18 179.0(17) . . . . ?
N3 C14 C15' C17' 177(2) . . . . ?
C19 C14 C15' C17' 57(3) . . . . ?
N3 C14 C15' C16' 50(3) . . . . ?
C19 C14 C15' C16' -71(3) . . . . ?
C14 C15' C17' C18' 64(3) . . . . ?
C16' C15' C17' C18' -167(3) . . . . ?
N3 C14 C19 O6 149.3(4) . . . . ?
C15 C14 C19 O6 -82.3(12) . . . . ?
C15' C14 C19 O6 -93.6(15) . . . . ?
N3 C14 C19 N4 -33.3(6) . . . . ?
C15 C14 C19 N4 95.2(12) . . . . ?
C15' C14 C19 N4 83.9(15) . . . . ?
N4 C20 C21 C22 -60.7(5) . . . . ?
C25 C20 C21 C22 175.7(4) . . . . ?
C20 C21 C22 C23 -61.0(7) . . . . ?
C20 C21 C22 C24 173.0(5) . . . . ?
N4 C20 C25 O7 137.5(5) . . . . ?
C21 C20 C25 O7 -98.7(6) . . . . ?
N4 C20 C25 O8 -45.6(5) . . . . ?
C21 C20 C25 O8 78.1(4) . . . . ?
C6 C1 N1 S1 -94.6(4) . . . . ?
C2 C1 N1 S1 140.2(3) . . . . ?
O3 C6 N2 C7 -6.0(8) . . . . ?
C1 C6 N2 C7 173.4(6) . . . . ?
C12 C7 N2 C6 -79.7(7) . . . . ?
C8 C7 N2 C6 162.3(9) . . . . ?
C8' C7 N2 C6 152.9(13) . . . . ?
C15 C14 N3 S1 160.1(13) . . . . ?
C19 C14 N3 S1 -69.9(5) . . . . ?
C15' C14 N3 S1 170.7(19) . . . . ?
O6 C19 N4 C20 -3.1(6) . . . . ?
C14 C19 N4 C20 179.5(4) . . . . ?
C25 C20 N4 C19 -77.3(5) . . . . ?
C21 C20 N4 C19 160.4(4) . . . . ?
O4 C12 O5 C13 -2.1(12) . . . . ?
C7 C12 O5 C13 178.5(6) . . . . ?
O7 C25 O8 C26 1.2(7) . . . . ?
C20 C25 O8 C26 -175.7(5) . . . . ?
C14 N3 S1 O2 7.2(4) . . . . ?
C14 N3 S1 O1 -124.8(4) . . . . ?
C14 N3 S1 N1 121.0(3) . . . . ?
C1 N1 S1 O2 176.8(3) . . . . ?
C1 N1 S1 O1 -53.1(3) . . . . ?
C1 N1 S1 N3 61.8(4) . . . . ?

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
C1 H1 O6 0.98 2.49 3.180(5) 127.3 4_645
C13 H13A O1 0.96 2.52 3.444(9) 162.6 2_554
C21 H21A O3 0.97 2.54 3.223(5) 127.5 .
C26 H26C O4 0.96 2.64 3.536(10) 155.6 4
N1 H1A O8 0.93(5) 2.37(5) 3.261(5) 160(4) .
N2 H2A O6 0.70(4) 2.19(5) 2.862(6) 161(5) 4_645
N3 H3 O7 0.80(5) 2.21(5) 2.994(5) 167(5) 4_645
N4 H4 O3 0.87(4) 2.08(5) 2.911(5) 160(4) .
C1 H1 O6 0.98 2.49 3.180(5) 127.3 4_645
C13 H13A O1 0.96 2.52 3.444(9) 162.6 2_554
C21 H21A O3 0.97 2.54 3.223(5) 127.5 .
C26 H26C O4 0.96 2.64 3.536(10) 155.6 4
N1 H1A O8 0.93(5) 2.37(5) 3.261(5) 160(4) .
N2 H2A O6 0.70(4) 2.19(5) 2.862(6) 161(5) 4_645
N3 H3 O7 0.80(5) 2.21(5) 2.994(5) 167(5) 4_645
N4 H4 O3 0.87(4) 2.08(5) 2.911(5) 160(4) .

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_leunew
_database_code_depnum_ccdc_archive 'CCDC 1583457'
_audit_update_record             
;
2017-11-01 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H50 N4 O8 S'
_chemical_formula_weight         578.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.0952(13)
_cell_length_b                   16.406(2)
_cell_length_c                   10.2489(14)
_cell_angle_alpha                90
_cell_angle_beta                 90.105(3)
_cell_angle_gamma                90
_cell_volume                     1697.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4544
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      22.1

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_F_000             628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17341
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.987
_diffrn_reflns_theta_max         24.482
_diffrn_reflns_theta_full        24.482
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5633
_reflns_number_gt                3340
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'


_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)+(0.0583P)²+1.0115P] 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_abs_structure_details 
;
 Flack x determined using 1132 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5633
_refine_ls_number_parameters     415
_refine_ls_number_restraints     157
_refine_ls_R_factor_all          0.1287
_refine_ls_R_factor_gt           0.0700
_refine_ls_wR_factor_ref         0.1725
_refine_ls_wR_factor_gt          0.1457
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.004
_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 0.0305(11) 0.3556(9) 0.3688(13) 0.164(6) Uani 1 1 d . . . . .
H1A H -0.0311 0.3968 0.3960 0.246 Uiso 1 1 calc R U . . .
H1B H 0.0750 0.3337 0.4439 0.246 Uiso 1 1 calc R U . . .
H1C H -0.0164 0.3127 0.3248 0.246 Uiso 1 1 calc R U . . .
C2 C 0.0658(11) 0.4242(7) 0.1539(11) 0.133(4) Uani 1 1 d . . . . .
H2A H 0.1322 0.4444 0.0953 0.199 Uiso 1 1 calc R U . . .
H2B H 0.0058 0.4674 0.1758 0.199 Uiso 1 1 calc R U . . .
H2C H 0.0178 0.3807 0.1127 0.199 Uiso 1 1 calc R U . . .
C3 C 0.1315(9) 0.3927(6) 0.2769(10) 0.096(3) Uani 1 1 d . . . . .
H3 H 0.1913 0.3487 0.2505 0.115 Uiso 1 1 calc R U . . .
C4 C 0.2142(7) 0.4561(5) 0.3394(8) 0.081(2) Uani 1 1 d . . . . .
H4A H 0.1557 0.5001 0.3652 0.097 Uiso 1 1 calc R U . . .
H4B H 0.2729 0.4777 0.2731 0.097 Uiso 1 1 calc R U . . .
C5 C 0.2988(8) 0.4342(6) 0.4575(8) 0.084(3) Uani 1 1 d . . . . .
H5 H 0.2378 0.4182 0.5272 0.100 Uiso 1 1 calc R U . . .
C6 C 0.3830(8) 0.3606(6) 0.4272(8) 0.083(3) Uani 1 1 d . . . . .
C7 C 0.5944(8) 0.3127(5) 0.3355(11) 0.096(3) Uani 1 1 d . . . . .
H7 H 0.5439 0.2634 0.3141 0.115 Uiso 1 1 calc R U . . .
C8 C 0.6763(9) 0.3373(5) 0.2147(10) 0.091(3) Uani 1 1 d . . . . .
H8A H 0.7384 0.3795 0.2406 0.109 Uiso 1 1 calc R U . . .
H8B H 0.7277 0.2905 0.1871 0.109 Uiso 1 1 calc R U . . .
C9 C 0.5979(11) 0.3681(7) 0.0986(12) 0.120(4) Uani 1 1 d . . . . .
H9 H 0.5551 0.4188 0.1265 0.144 Uiso 1 1 calc R U . . .
C10 C 0.4909(18) 0.3129(12) 0.0557(17) 0.242(10) Uani 1 1 d . . . . .
H10A H 0.4458 0.3364 -0.0178 0.362 Uiso 1 1 calc R U . . .
H10B H 0.5280 0.2613 0.0312 0.362 Uiso 1 1 calc R U . . .
H10C H 0.4292 0.3052 0.1258 0.362 Uiso 1 1 calc R U . . .
C11 C 0.6897(16) 0.3906(13) -0.0125(13) 0.223(9) Uani 1 1 d . . . . .
H11A H 0.7210 0.3418 -0.0540 0.334 Uiso 1 1 calc R U . . .
H11B H 0.7636 0.4209 0.0210 0.334 Uiso 1 1 calc R U . . .
H11C H 0.6425 0.4232 -0.0749 0.334 Uiso 1 1 calc R U . . .
C12 C 0.6843(9) 0.2939(6) 0.4557(14) 0.095(3) Uani 1 1 d . . . . .
C13 C 0.8374(12) 0.2044(9) 0.5398(15) 0.180(7) Uani 1 1 d . . . . .
H13A H 0.7842 0.1961 0.6162 0.270 Uiso 1 1 calc R U . . .
H13B H 0.9010 0.2467 0.5564 0.270 Uiso 1 1 calc R U . . .
H13C H 0.8828 0.1548 0.5185 0.270 Uiso 1 1 calc R U . . .
C14 C 0.828(2) 0.594(2) 0.821(2) 0.134(8) Uani 0.55(3) 1 d D U P A 1
H14A H 0.8980 0.6331 0.8277 0.200 Uiso 0.55(3) 1 calc R U P A 1
H14B H 0.8102 0.5710 0.9053 0.200 Uiso 0.55(3) 1 calc R U P A 1
H14C H 0.7494 0.6201 0.7884 0.200 Uiso 0.55(3) 1 calc R U P A 1
C15 C 1.018(3) 0.519(3) 0.724(4) 0.145(9) Uani 0.55(3) 1 d D U P A 1
H15A H 1.0420 0.4655 0.6935 0.217 Uiso 0.55(3) 1 calc R U P A 1
H15B H 1.0532 0.5269 0.8103 0.217 Uiso 0.55(3) 1 calc R U P A 1
H15C H 1.0538 0.5593 0.6664 0.217 Uiso 0.55(3) 1 calc R U P A 1
C16 C 0.869(3) 0.526(2) 0.728(2) 0.117(6) Uani 0.55(3) 1 d D U P A 1
H16 H 0.8261 0.4744 0.7491 0.140 Uiso 0.55(3) 1 calc R U P A 1
C17 C 0.833(6) 0.555(4) 0.591(3) 0.098(7) Uani 0.55(3) 1 d D U P A 1
H17A H 0.8632 0.5149 0.5288 0.118 Uiso 0.55(3) 1 calc R U P A 1
H17B H 0.8786 0.6057 0.5738 0.118 Uiso 0.55(3) 1 calc R U P A 1
C14' C 0.863(4) 0.655(3) 0.778(4) 0.165(12) Uani 0.45(3) 1 d D U P A 2
H14D H 0.9298 0.6686 0.8408 0.247 Uiso 0.45(3) 1 calc R U P A 2
H14E H 0.7770 0.6619 0.8159 0.247 Uiso 0.45(3) 1 calc R U P A 2
H14F H 0.8712 0.6911 0.7037 0.247 Uiso 0.45(3) 1 calc R U P A 2
C15' C 1.025(4) 0.544(3) 0.757(5) 0.145(11) Uani 0.45(3) 1 d D U P A 2
H15D H 1.0458 0.4953 0.7103 0.218 Uiso 0.45(3) 1 calc R U P A 2
H15E H 1.0392 0.5354 0.8490 0.218 Uiso 0.45(3) 1 calc R U P A 2
H15F H 1.0817 0.5877 0.7280 0.218 Uiso 0.45(3) 1 calc R U P A 2
C16' C 0.881(3) 0.567(2) 0.733(3) 0.112(7) Uani 0.45(3) 1 d D U P A 2
H16' H 0.8295 0.5347 0.7955 0.135 Uiso 0.45(3) 1 calc R U P A 2
C17' C 0.821(8) 0.548(4) 0.600(4) 0.103(8) Uani 0.45(3) 1 d D U P A 2
H17C H 0.8751 0.5758 0.5357 0.123 Uiso 0.45(3) 1 calc R U P A 2
H17D H 0.8320 0.4902 0.5859 0.123 Uiso 0.45(3) 1 calc R U P A 2
C18 C 0.6806(8) 0.5686(5) 0.5715(7) 0.070(2) Uani 1 1 d . . . . .
H18 H 0.6546 0.6188 0.6163 0.084 Uiso 1 1 calc R U . A 1
C19 C 0.6584(7) 0.5796(5) 0.4250(7) 0.0615(18) Uani 1 1 d . . . . .
C20 C 0.6256(8) 0.6782(4) 0.2522(7) 0.070(2) Uani 1 1 d . . . . .
H20 H 0.6065 0.7368 0.2512 0.084 Uiso 1 1 calc DR U . . .
C21 C 0.7493(8) 0.6653(5) 0.1696(8) 0.080(2) Uani 1 1 d . . . . .
H21A H 0.7693 0.6075 0.1682 0.096 Uiso 1 1 calc R U . . .
H21B H 0.7294 0.6817 0.0807 0.096 Uiso 1 1 calc R U . . .
C22 C 0.8712(10) 0.7105(6) 0.2140(10) 0.106(3) Uani 1 1 d . . . . .
H22 H 0.8883 0.6949 0.3048 0.128 Uiso 1 1 calc R U . . .
C23 C 0.8542(12) 0.7997(7) 0.2106(15) 0.157(5) Uani 1 1 d . . . . .
H23A H 0.7768 0.8145 0.2595 0.235 Uiso 1 1 calc R U . . .
H23B H 0.8441 0.8173 0.1218 0.235 Uiso 1 1 calc R U . . .
H23C H 0.9306 0.8254 0.2483 0.235 Uiso 1 1 calc R U . . .
C24 C 0.9943(11) 0.6871(9) 0.1336(13) 0.154(5) Uani 1 1 d . . . . .
H24A H 1.0728 0.7029 0.1803 0.232 Uiso 1 1 calc R U . . .
H24B H 0.9918 0.7147 0.0511 0.232 Uiso 1 1 calc R U . . .
H24C H 0.9952 0.6293 0.1195 0.232 Uiso 1 1 calc R U . . .
C25 C 0.5014(9) 0.6349(5) 0.2033(8) 0.075(2) Uani 1 1 d . . . . .
C26 C 0.3852(12) 0.5862(9) 0.0162(10) 0.147(5) Uani 1 1 d . . . . .
H26A H 0.3095 0.6179 0.0413 0.221 Uiso 1 1 calc R U . . .
H26B H 0.3740 0.5310 0.0453 0.221 Uiso 1 1 calc R U . . .
H26C H 0.3938 0.5870 -0.0771 0.221 Uiso 1 1 calc R U . . .
N1 N 0.3685(7) 0.5059(6) 0.5027(6) 0.082(2) Uani 1 1 d . . . . .
N2 N 0.5023(7) 0.3761(4) 0.3709(7) 0.079(2) Uani 1 1 d . . . . .
N3 N 0.6034(7) 0.5022(6) 0.6222(6) 0.088(2) Uani 1 1 d . . . . .
H3A H 0.620(10) 0.453(6) 0.603(10) 0.106 Uiso 1 1 d . U . . .
N4 N 0.6465(6) 0.6551(4) 0.3889(6) 0.0701(18) Uani 1 1 d D . . . .
O1 O 0.4013(8) 0.4449(7) 0.7136(7) 0.161(4) Uani 1 1 d . . . . .
O2 O 0.4270(7) 0.5984(5) 0.6899(7) 0.132(3) Uani 1 1 d . . . . .
O3 O 0.3458(6) 0.2905(4) 0.4444(7) 0.124(3) Uani 1 1 d . . . . .
O4 O 0.6926(9) 0.3363(6) 0.5494(10) 0.143(3) Uani 1 1 d . . . . .
O5 O 0.7526(7) 0.2283(5) 0.4311(9) 0.140(3) Uani 1 1 d . . . . .
O6 O 0.6546(5) 0.5216(3) 0.3497(4) 0.0705(13) Uani 1 1 d . . . . .
O7 O 0.4073(6) 0.6186(4) 0.2689(5) 0.0896(17) Uani 1 1 d . . . . .
O8 O 0.5064(6) 0.6213(4) 0.0766(5) 0.100(2) Uani 1 1 d . . . . .
S1 S 0.4440(2) 0.5141(2) 0.6430(2) 0.1059(9) Uani 1 1 d . . . . .
H2 H 0.522(5) 0.429(4) 0.366(5) 0.041(16) Uiso 1 1 d . . . . .
H4 H 0.646(6) 0.697(2) 0.438(3) 0.06(2) Uiso 1 1 d D . . . .
H1 H 0.386(8) 0.547(5) 0.447(9) 0.11(3) Uiso 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 C3 1.518(13) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.514(12) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.478(12) . ?
C3 H3 0.9800 . ?
C4 C5 1.523(10) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N1 1.447(12) . ?
C5 C6 1.510(12) . ?
C5 H5 0.9800 . ?
C6 O3 1.223(9) . ?
C6 N2 1.360(10) . ?
C7 N2 1.443(11) . ?
C7 C8 1.544(13) . ?
C7 C12 1.559(14) . ?
C7 H7 0.9800 . ?
C8 C9 1.514(13) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.477(17) . ?
C9 C11 1.514(17) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O4 1.189(13) . ?
C12 O5 1.304(12) . ?
C13 O5 1.457(14) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C16 1.52(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.514(19) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.52(2) . ?
C16 H16 0.9800 . ?
C17 C18 1.56(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C14' C16' 1.52(2) . ?
C14' H14D 0.9600 . ?
C14' H14E 0.9600 . ?
C14' H14F 0.9600 . ?
C15' C16' 1.53(2) . ?
C15' H15D 0.9600 . ?
C15' H15E 0.9600 . ?
C15' H15F 0.9600 . ?
C16' C17' 1.52(2) . ?
C16' H16' 0.9800 . ?
C17' C18 1.49(8) . ?
C17' H17C 0.9700 . ?
C17' H17D 0.9700 . ?
C18 N3 1.436(11) . ?
C18 C19 1.528(10) . ?
C18 H18 0.9800 . ?
C19 O6 1.226(8) . ?
C19 N4 1.298(9) . ?
C20 N4 1.466(9) . ?
C20 C21 1.525(10) . ?
C20 C25 1.526(11) . ?
C20 H20 0.9800 . ?
C21 C22 1.506(11) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.475(15) . ?
C22 C24 1.541(14) . ?
C22 H22 0.9800 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O7 1.194(9) . ?
C25 O8 1.318(9) . ?
C26 O8 1.487(11) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
N1 S1 1.632(7) . ?
N1 H1 0.90(9) . ?
N2 H2 0.89(6) . ?
N3 S1 1.636(8) . ?
N3 H3A 0.85(9) . ?
N4 H4 0.86(3) . ?
O1 S1 1.413(9) . ?
O2 S1 1.475(8) . ?

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
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 C2 111.5(8) . . ?
C4 C3 C1 113.1(9) . . ?
C2 C3 C1 111.1(9) . . ?
C4 C3 H3 106.9 . . ?
C2 C3 H3 106.9 . . ?
C1 C3 H3 106.9 . . ?
C3 C4 C5 119.6(7) . . ?
C3 C4 H4A 107.4 . . ?
C5 C4 H4A 107.4 . . ?
C3 C4 H4B 107.4 . . ?
C5 C4 H4B 107.4 . . ?
H4A C4 H4B 106.9 . . ?
N1 C5 C6 116.3(7) . . ?
N1 C5 C4 109.6(7) . . ?
C6 C5 C4 109.9(7) . . ?
N1 C5 H5 106.9 . . ?
C6 C5 H5 106.9 . . ?
C4 C5 H5 106.9 . . ?
O3 C6 N2 120.7(9) . . ?
O3 C6 C5 123.4(8) . . ?
N2 C6 C5 115.9(7) . . ?
N2 C7 C8 111.1(7) . . ?
N2 C7 C12 108.5(9) . . ?
C8 C7 C12 111.9(7) . . ?
N2 C7 H7 108.4 . . ?
C8 C7 H7 108.4 . . ?
C12 C7 H7 108.4 . . ?
C9 C8 C7 115.9(8) . . ?
C9 C8 H8A 108.3 . . ?
C7 C8 H8A 108.3 . . ?
C9 C8 H8B 108.3 . . ?
C7 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C10 C9 C8 114.2(12) . . ?
C10 C9 C11 111.9(13) . . ?
C8 C9 C11 110.6(10) . . ?
C10 C9 H9 106.5 . . ?
C8 C9 H9 106.5 . . ?
C11 C9 H9 106.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 O5 127.0(11) . . ?
O4 C12 C7 124.3(10) . . ?
O5 C12 C7 108.5(11) . . ?
O5 C13 H13A 109.5 . . ?
O5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 C14 H14A 109.5 . . ?
C16 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C16 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C15 C16 C17 104(4) . . ?
C15 C16 C14 110.2(18) . . ?
C17 C16 C14 107(3) . . ?
C15 C16 H16 111.8 . . ?
C17 C16 H16 111.8 . . ?
C14 C16 H16 111.8 . . ?
C16 C17 C18 114(4) . . ?
C16 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C16' C14' H14D 109.5 . . ?
C16' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
C16' C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?
C16' C15' H15D 109.5 . . ?
C16' C15' H15E 109.5 . . ?
H15D C15' H15E 109.5 . . ?
C16' C15' H15F 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
C17' C16' C14' 115(4) . . ?
C17' C16' C15' 118(4) . . ?
C14' C16' C15' 107(2) . . ?
C17' C16' H16' 105.3 . . ?
C14' C16' H16' 105.3 . . ?
C15' C16' H16' 105.3 . . ?
C18 C17' C16' 120(6) . . ?
C18 C17' H17C 107.2 . . ?
C16' C17' H17C 107.2 . . ?
C18 C17' H17D 107.2 . . ?
C16' C17' H17D 107.2 . . ?
H17C C17' H17D 106.8 . . ?
N3 C18 C17' 106(3) . . ?
N3 C18 C19 111.5(6) . . ?
C17' C18 C19 111(2) . . ?
N3 C18 C17 112(2) . . ?
C19 C18 C17 106.7(14) . . ?
N3 C18 H18 108.8 . . ?
C19 C18 H18 108.8 . . ?
C17 C18 H18 108.8 . . ?
O6 C19 N4 124.0(7) . . ?
O6 C19 C18 122.1(7) . . ?
N4 C19 C18 113.9(7) . . ?
N4 C20 C21 112.2(7) . . ?
N4 C20 C25 108.1(6) . . ?
C21 C20 C25 115.2(6) . . ?
N4 C20 H20 107.0 . . ?
C21 C20 H20 107.0 . . ?
C25 C20 H20 107.0 . . ?
C22 C21 C20 115.7(7) . . ?
C22 C21 H21A 108.4 . . ?
C20 C21 H21A 108.4 . . ?
C22 C21 H21B 108.4 . . ?
C20 C21 H21B 108.4 . . ?
H21A C21 H21B 107.4 . . ?
C23 C22 C21 112.7(10) . . ?
C23 C22 C24 109.1(9) . . ?
C21 C22 C24 112.1(8) . . ?
C23 C22 H22 107.5 . . ?
C21 C22 H22 107.5 . . ?
C24 C22 H22 107.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O7 C25 O8 123.3(8) . . ?
O7 C25 C20 124.9(7) . . ?
O8 C25 C20 111.6(7) . . ?
O8 C26 H26A 109.5 . . ?
O8 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O8 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C5 N1 S1 125.1(7) . . ?
C5 N1 H1 120(6) . . ?
S1 N1 H1 114(6) . . ?
C6 N2 C7 122.9(7) . . ?
C6 N2 H2 114(4) . . ?
C7 N2 H2 123(4) . . ?
C18 N3 S1 119.4(6) . . ?
C18 N3 H3A 122(7) . . ?
S1 N3 H3A 110(7) . . ?
C19 N4 C20 122.1(6) . . ?
C19 N4 H4 127(2) . . ?
C20 N4 H4 110(2) . . ?
C12 O5 C13 112.6(11) . . ?
C25 O8 C26 116.2(7) . . ?
O1 S1 O2 123.4(5) . . ?
O1 S1 N1 104.1(5) . . ?
O2 S1 N1 108.0(5) . . ?
O1 S1 N3 105.8(5) . . ?
O2 S1 N3 105.6(5) . . ?
N1 S1 N3 109.5(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 C4 C5 -174.3(8) . . . . ?
C1 C3 C4 C5 59.6(12) . . . . ?
C3 C4 C5 N1 -179.0(8) . . . . ?
C3 C4 C5 C6 52.1(10) . . . . ?
N1 C5 C6 O3 146.5(8) . . . . ?
C4 C5 C6 O3 -88.3(9) . . . . ?
N1 C5 C6 N2 -37.5(10) . . . . ?
C4 C5 C6 N2 87.7(9) . . . . ?
N2 C7 C8 C9 -50.3(11) . . . . ?
C12 C7 C8 C9 -171.7(8) . . . . ?
C7 C8 C9 C10 -52.9(14) . . . . ?
C7 C8 C9 C11 179.7(11) . . . . ?
N2 C7 C12 O4 -14.1(13) . . . . ?
C8 C7 C12 O4 108.8(13) . . . . ?
N2 C7 C12 O5 169.9(7) . . . . ?
C8 C7 C12 O5 -67.2(9) . . . . ?
C15 C16 C17 C18 -179(3) . . . . ?
C14 C16 C17 C18 -63(5) . . . . ?
C14' C16' C17' C18 -53(6) . . . . ?
C15' C16' C17' C18 179(4) . . . . ?
C16' C17' C18 N3 -83(5) . . . . ?
C16' C17' C18 C19 155(4) . . . . ?
C16 C17 C18 N3 -46(5) . . . . ?
C16 C17 C18 C19 -168(3) . . . . ?
N3 C18 C19 O6 -43.6(9) . . . . ?
C17' C18 C19 O6 75(3) . . . . ?
C17 C18 C19 O6 79(2) . . . . ?
N3 C18 C19 N4 137.6(7) . . . . ?
C17' C18 C19 N4 -104(3) . . . . ?
C17 C18 C19 N4 -100(2) . . . . ?
N4 C20 C21 C22 -58.1(9) . . . . ?
C25 C20 C21 C22 177.7(7) . . . . ?
C20 C21 C22 C23 -62.2(11) . . . . ?
C20 C21 C22 C24 174.2(9) . . . . ?
N4 C20 C25 O7 32.1(10) . . . . ?
C21 C20 C25 O7 158.5(8) . . . . ?
N4 C20 C25 O8 -151.6(6) . . . . ?
C21 C20 C25 O8 -25.2(9) . . . . ?
C6 C5 N1 S1 -68.3(9) . . . . ?
C4 C5 N1 S1 166.3(6) . . . . ?
O3 C6 N2 C7 -3.7(13) . . . . ?
C5 C6 N2 C7 -179.8(8) . . . . ?
C8 C7 N2 C6 148.7(8) . . . . ?
C12 C7 N2 C6 -87.8(9) . . . . ?
C17' C18 N3 S1 164(2) . . . . ?
C19 C18 N3 S1 -75.1(8) . . . . ?
C17 C18 N3 S1 165.3(19) . . . . ?
O6 C19 N4 C20 0.8(11) . . . . ?
C18 C19 N4 C20 179.6(6) . . . . ?
C21 C20 N4 C19 -71.4(9) . . . . ?
C25 C20 N4 C19 56.8(9) . . . . ?
O4 C12 O5 C13 5.8(15) . . . . ?
C7 C12 O5 C13 -178.4(8) . . . . ?
O7 C25 O8 C26 1.8(13) . . . . ?
C20 C25 O8 C26 -174.6(8) . . . . ?
C5 N1 S1 O1 -11.7(8) . . . . ?
C5 N1 S1 O2 -144.4(7) . . . . ?
C5 N1 S1 N3 101.0(7) . . . . ?
C18 N3 S1 O1 -170.2(6) . . . . ?
C18 N3 S1 O2 -37.9(7) . . . . ?
C18 N3 S1 N1 78.2(7) . . . . ?

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
C13 H13A O7 0.96 2.60 3.456(13) 149.0 2_646
C21 H21A O6 0.97 2.61 3.144(9) 115.2 .
C26 H26C O2 0.96 2.42 3.377(12) 175.4 1_554
N3 H3A O4 0.85(9) 2.12(9) 2.962(14) 171(10) .
N2 H2 O6 0.89(6) 2.03(6) 2.847(8) 152(5) .
N4 H4 O3 0.86(3) 1.95(3) 2.803(8) 176(5) 2_656
N1 H1 O7 0.90(9) 2.18(9) 3.053(10) 162(8) .
C13 H13A O7 0.96 2.60 3.456(13) 149.0 2_646
C21 H21A O6 0.97 2.61 3.144(9) 115.2 .
C26 H26C O2 0.96 2.42 3.377(12) 175.4 1_554
N3 H3A O4 0.85(9) 2.12(9) 2.962(14) 171(10) .
N2 H2 O6 0.89(6) 2.03(6) 2.847(8) 152(5) .
N4 H4 O3 0.86(3) 1.95(3) 2.803(8) 176(5) 2_656
N1 H1 O7 0.90(9) 2.18(9) 3.053(10) 162(8) .

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_VAL
_database_code_depnum_ccdc_archive 'CCDC 1583458'
_audit_update_record             
;
2017-11-01 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H46 N4 O8 S'
_chemical_formula_sum            'C24 H46 N4 O8 S'
_chemical_formula_weight         550.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.5629(6)
_cell_length_b                   15.7440(9)
_cell_length_c                   21.1445(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3183.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9924
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      26.51

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.148
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6532
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (bruker, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54270
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.320
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_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 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6251
_reflns_number_gt                4093
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'


_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)+(0.0585P)²+0.8111P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0041(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1422 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6251
_refine_ls_number_parameters     370
_refine_ls_number_restraints     68
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1355
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.061
_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 0.4983(10) 0.4992(7) 0.4888(3) 0.173(5) Uani 1 1 d . . . . .
H1A H 0.5116 0.4813 0.5318 0.260 Uiso 1 1 calc R U . . .
H1B H 0.4362 0.5470 0.4878 0.260 Uiso 1 1 calc R U . . .
H1C H 0.4587 0.4533 0.4648 0.260 Uiso 1 1 calc R U . . .
C2 C 0.6272(7) 0.5488(3) 0.4022(2) 0.0672(14) Uani 1 1 d . . . . .
C3 C 0.7700(5) 0.5763(3) 0.3820(2) 0.0599(12) Uani 1 1 d . . . . .
H3 H 0.8385 0.5365 0.3995 0.072 Uiso 1 1 calc R U . . .
C4 C 0.8041(7) 0.6660(4) 0.4069(3) 0.090(2) Uani 1 1 d . U . . .
H4 H 0.8843 0.6865 0.3823 0.108 Uiso 1 1 calc R U . . .
C5 C 0.6863(9) 0.7273(4) 0.3951(4) 0.133(3) Uani 1 1 d . . . . .
H5A H 0.6603 0.7253 0.3512 0.200 Uiso 1 1 calc R U . . .
H5B H 0.6074 0.7119 0.4207 0.200 Uiso 1 1 calc R U . . .
H5C H 0.7160 0.7837 0.4058 0.200 Uiso 1 1 calc R U . . .
C8 C 0.7885(5) 0.5028(2) 0.28185(19) 0.0487(10) Uani 1 1 d . . . . .
C9 C 0.7959(5) 0.5108(2) 0.21103(19) 0.0497(11) Uani 1 1 d . . . . .
H9 H 0.8595 0.5579 0.2013 0.060 Uiso 1 1 calc R U . . .
C10 C 0.6552(5) 0.5317(3) 0.1817(2) 0.0678(13) Uani 1 1 d . . . . .
H10 H 0.6199 0.5826 0.2031 0.081 Uiso 1 1 calc R U . . .
C11 C 0.5490(7) 0.4626(4) 0.1919(3) 0.104(2) Uani 1 1 d . . . . .
H11A H 0.4621 0.4787 0.1726 0.155 Uiso 1 1 calc R U . . .
H11B H 0.5820 0.4108 0.1732 0.155 Uiso 1 1 calc R U . . .
H11C H 0.5351 0.4543 0.2364 0.155 Uiso 1 1 calc R U . . .
C12 C 0.6721(7) 0.5541(4) 0.1119(3) 0.103(2) Uani 1 1 d . . . . .
H12A H 0.7406 0.5983 0.1075 0.155 Uiso 1 1 calc R U . . .
H12B H 0.7022 0.5047 0.0890 0.155 Uiso 1 1 calc R U . . .
H12C H 0.5842 0.5733 0.0953 0.155 Uiso 1 1 calc R U . . .
C13 C 1.1881(5) 0.3657(2) 0.2637(2) 0.0506(11) Uani 1 1 d . . . . .
H13 H 1.2565 0.3546 0.2301 0.061 Uiso 1 1 calc R U . . .
C14 C 1.2685(5) 0.3966(3) 0.3220(3) 0.0666(14) Uani 1 1 d . . . . .
H14 H 1.3168 0.4489 0.3096 0.080 Uiso 1 1 calc R U . . .
C15 C 1.3805(7) 0.3335(4) 0.3406(3) 0.106(2) Uani 1 1 d . . . . .
H15A H 1.4377 0.3208 0.3046 0.159 Uiso 1 1 calc R U . . .
H15B H 1.4374 0.3573 0.3735 0.159 Uiso 1 1 calc R U . . .
H15C H 1.3373 0.2822 0.3556 0.159 Uiso 1 1 calc R U . . .
C16 C 1.1745(7) 0.4192(4) 0.3770(3) 0.0941(19) Uani 1 1 d . . . . .
H16A H 1.1052 0.4593 0.3632 0.141 Uiso 1 1 calc R U . . .
H16B H 1.1293 0.3689 0.3923 0.141 Uiso 1 1 calc R U . . .
H16C H 1.2295 0.4439 0.4102 0.141 Uiso 1 1 calc R U . . .
C17 C 1.1080(5) 0.2836(2) 0.27555(19) 0.0478(10) Uani 1 1 d . . . . .
C18 C 0.8903(5) 0.2150(2) 0.3064(2) 0.0547(12) Uani 1 1 d . . . . .
H18 H 0.9502 0.1706 0.3244 0.066 Uiso 1 1 calc R U . . .
C19 C 0.8340(5) 0.1829(3) 0.2447(3) 0.0693(15) Uani 1 1 d . . . . .
C20 C 0.7188(10) 0.2186(4) 0.1498(4) 0.149(4) Uani 1 1 d . . . . .
H20A H 0.6787 0.2672 0.1293 0.223 Uiso 1 1 calc R U . . .
H20B H 0.7925 0.1959 0.1240 0.223 Uiso 1 1 calc R U . . .
H20C H 0.6480 0.1761 0.1558 0.223 Uiso 1 1 calc R U . . .
C21 C 0.7747(6) 0.2339(3) 0.3540(3) 0.0772(16) Uani 1 1 d D U . . .
H21 H 0.7263 0.2862 0.3418 0.093 Uiso 1 1 calc R U . A 1
C22 C 0.6697(7) 0.1615(4) 0.3574(5) 0.130(3) Uani 1 1 d . . . . .
H22A H 0.5984 0.1752 0.3877 0.196 Uiso 1 1 calc R U . . .
H22B H 0.6279 0.1533 0.3166 0.196 Uiso 1 1 calc R U . . .
H22C H 0.7166 0.1104 0.3701 0.196 Uiso 1 1 calc R U . . .
O1 O 0.5241(4) 0.5481(2) 0.37020(18) 0.0877(11) Uani 1 1 d . . . . .
O2 O 0.6325(5) 0.5230(3) 0.46162(17) 0.1114(16) Uani 1 1 d . . . . .
O3 O 0.7838(3) 0.43286(17) 0.30848(13) 0.0616(8) Uani 1 1 d . . . . .
O4 O 1.0595(4) 0.5052(2) 0.13932(14) 0.0699(9) Uani 1 1 d . . . . .
O5 O 1.0507(4) 0.34851(19) 0.14706(15) 0.0703(9) Uani 1 1 d . . . . .
O6 O 1.1665(3) 0.21553(17) 0.26864(16) 0.0623(8) Uani 1 1 d . . . . .
O7 O 0.7749(4) 0.24353(19) 0.21059(18) 0.0883(13) Uani 1 1 d . . . . .
O8 O 0.8409(5) 0.1114(2) 0.2264(2) 0.1116(16) Uani 1 1 d . . . . .
S1 S 1.02256(12) 0.42999(7) 0.17246(5) 0.0548(3) Uani 1 1 d . . . . .
N1 N 0.7816(4) 0.5749(2) 0.31407(17) 0.0575(10) Uani 1 1 d D . . . .
N2 N 0.8545(4) 0.4338(2) 0.18247(16) 0.0494(8) Uani 1 1 d D . . . .
N3 N 1.0951(4) 0.4339(2) 0.24164(16) 0.0493(8) Uani 1 1 d D . . . .
N4 N 0.9770(4) 0.29052(19) 0.29597(16) 0.0488(9) Uani 1 1 d D . . . .
C23 C 0.8436(17) 0.2463(8) 0.4195(5) 0.116(4) Uani 0.788(15) 1 d D U P B 1
H23A H 0.8787 0.1921 0.4342 0.139 Uiso 0.788(15) 1 calc R U P B 1
H23B H 0.9227 0.2844 0.4150 0.139 Uiso 0.788(15) 1 calc R U P B 1
C24 C 0.7450(16) 0.2819(9) 0.4681(5) 0.182(6) Uani 0.788(15) 1 d D U P B 1
H24A H 0.7933 0.2882 0.5076 0.273 Uiso 0.788(15) 1 calc R U P B 1
H24B H 0.7114 0.3362 0.4542 0.273 Uiso 0.788(15) 1 calc R U P B 1
H24C H 0.6675 0.2438 0.4734 0.273 Uiso 0.788(15) 1 calc R U P B 1
C23' C 0.814(7) 0.281(2) 0.4159(16) 0.101(9) Uani 0.212(15) 1 d D U P B 2
H23C H 0.8717 0.3298 0.4060 0.121 Uiso 0.212(15) 1 calc R U P B 2
H23D H 0.7304 0.3003 0.4369 0.121 Uiso 0.212(15) 1 calc R U P B 2
C24' C 0.895(5) 0.221(3) 0.4593(15) 0.155(14) Uani 0.212(15) 1 d D U P B 2
H24D H 0.9188 0.2508 0.4975 0.232 Uiso 0.212(15) 1 calc R U P B 2
H24E H 0.8373 0.1731 0.4694 0.232 Uiso 0.212(15) 1 calc R U P B 2
H24F H 0.9782 0.2025 0.4385 0.232 Uiso 0.212(15) 1 calc R U P B 2
C6 C 0.8476(12) 0.6672(6) 0.4747(4) 0.148(4) Uani 1 1 d D U . . .
H6A H 0.7721 0.6444 0.5002 0.178 Uiso 1 1 calc R U . . .
H6B H 0.8626 0.7256 0.4876 0.178 Uiso 1 1 calc R U . . .
C7 C 0.9844(14) 0.6147(9) 0.4882(5) 0.228(7) Uani 1 1 d D U . . .
H7A H 1.0066 0.6180 0.5324 0.342 Uiso 1 1 calc R U . . .
H7B H 0.9697 0.5564 0.4766 0.342 Uiso 1 1 calc R U . . .
H7C H 1.0603 0.6377 0.4639 0.342 Uiso 1 1 calc R U . . .
H4A H 0.938(4) 0.3412(18) 0.2997(19) 0.056(12) Uiso 1 1 d D . . . .
H2A H 0.823(4) 0.388(2) 0.2017(18) 0.055(12) Uiso 1 1 d D . . . .
H3A H 1.129(5) 0.485(2) 0.249(2) 0.082(16) Uiso 1 1 d D . . . .
H1D H 0.790(5) 0.619(2) 0.2888(19) 0.070(15) Uiso 1 1 d 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 O2 1.455(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.196(6) . ?
C2 O2 1.320(6) . ?
C2 C3 1.496(7) . ?
C3 N1 1.440(6) . ?
C3 C4 1.541(7) . ?
C3 H3 0.9800 . ?
C4 C6 1.493(10) . ?
C4 C5 1.504(10) . ?
C4 H4 0.9800 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C8 O3 1.237(4) . ?
C8 N1 1.326(5) . ?
C8 C9 1.504(6) . ?
C9 N2 1.466(5) . ?
C9 C10 1.518(6) . ?
C9 H9 0.9800 . ?
C10 C11 1.503(8) . ?
C10 C12 1.526(7) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N3 1.471(5) . ?
C13 C17 1.522(5) . ?
C13 C14 1.533(7) . ?
C13 H13 0.9800 . ?
C14 C16 1.511(8) . ?
C14 C15 1.513(7) . ?
C14 H14 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O6 1.218(5) . ?
C17 N4 1.330(5) . ?
C18 N4 1.466(5) . ?
C18 C19 1.500(7) . ?
C18 C21 1.525(7) . ?
C18 H18 0.9800 . ?
C19 O8 1.192(5) . ?
C19 O7 1.323(5) . ?
C20 O7 1.446(7) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.520(7) . ?
C21 C23 1.544(11) . ?
C21 C23' 1.55(2) . ?
C21 H21 0.9800 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O4 S1 1.421(3) . ?
O5 S1 1.417(3) . ?
S1 N3 1.620(4) . ?
S1 N2 1.622(4) . ?
N1 H1D 0.88(2) . ?
N2 H2A 0.88(2) . ?
N3 H3A 0.88(3) . ?
N4 H4A 0.88(2) . ?
C23 C24 1.502(16) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C23' C24' 1.52(3) . ?
C23' H23C 0.9700 . ?
C23' H23D 0.9700 . ?
C24' H24D 0.9600 . ?
C24' H24E 0.9600 . ?
C24' H24F 0.9600 . ?
C6 C7 1.574(13) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
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 . . ?
O1 C2 O2 124.6(5) . . ?
O1 C2 C3 126.3(4) . . ?
O2 C2 C3 109.0(5) . . ?
N1 C3 C2 110.6(4) . . ?
N1 C3 C4 109.8(4) . . ?
C2 C3 C4 111.2(4) . . ?
N1 C3 H3 108.4 . . ?
C2 C3 H3 108.4 . . ?
C4 C3 H3 108.4 . . ?
C6 C4 C5 111.1(7) . . ?
C6 C4 C3 113.5(6) . . ?
C5 C4 C3 111.9(5) . . ?
C6 C4 H4 106.6 . . ?
C5 C4 H4 106.6 . . ?
C3 C4 H4 106.6 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O3 C8 N1 121.7(4) . . ?
O3 C8 C9 122.0(3) . . ?
N1 C8 C9 116.2(3) . . ?
N2 C9 C8 111.0(3) . . ?
N2 C9 C10 110.5(3) . . ?
C8 C9 C10 112.5(4) . . ?
N2 C9 H9 107.5 . . ?
C8 C9 H9 107.5 . . ?
C10 C9 H9 107.5 . . ?
C11 C10 C9 112.6(4) . . ?
C11 C10 C12 112.2(5) . . ?
C9 C10 C12 110.5(4) . . ?
C11 C10 H10 107.1 . . ?
C9 C10 H10 107.1 . . ?
C12 C10 H10 107.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C17 111.6(3) . . ?
N3 C13 C14 109.0(3) . . ?
C17 C13 C14 112.9(4) . . ?
N3 C13 H13 107.7 . . ?
C17 C13 H13 107.7 . . ?
C14 C13 H13 107.7 . . ?
C16 C14 C15 112.0(5) . . ?
C16 C14 C13 113.3(4) . . ?
C15 C14 C13 110.8(4) . . ?
C16 C14 H14 106.7 . . ?
C15 C14 H14 106.7 . . ?
C13 C14 H14 106.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O6 C17 N4 122.9(4) . . ?
O6 C17 C13 119.8(4) . . ?
N4 C17 C13 117.3(4) . . ?
N4 C18 C19 110.2(3) . . ?
N4 C18 C21 110.6(3) . . ?
C19 C18 C21 112.3(4) . . ?
N4 C18 H18 107.9 . . ?
C19 C18 H18 107.9 . . ?
C21 C18 H18 107.9 . . ?
O8 C19 O7 121.8(5) . . ?
O8 C19 C18 125.5(5) . . ?
O7 C19 C18 112.6(4) . . ?
O7 C20 H20A 109.5 . . ?
O7 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O7 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C18 111.4(5) . . ?
C22 C21 C23 109.5(8) . . ?
C18 C21 C23 107.9(7) . . ?
C22 C21 C23' 119(2) . . ?
C18 C21 C23' 118(3) . . ?
C22 C21 H21 109.4 . . ?
C18 C21 H21 109.4 . . ?
C23 C21 H21 109.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C2 O2 C1 114.9(5) . . ?
C19 O7 C20 116.5(4) . . ?
O5 S1 O4 121.4(2) . . ?
O5 S1 N3 107.18(19) . . ?
O4 S1 N3 107.89(19) . . ?
O5 S1 N2 105.7(2) . . ?
O4 S1 N2 106.3(2) . . ?
N3 S1 N2 107.75(18) . . ?
C8 N1 C3 122.0(4) . . ?
C8 N1 H1D 111(3) . . ?
C3 N1 H1D 127(3) . . ?
C9 N2 S1 117.6(3) . . ?
C9 N2 H2A 111(3) . . ?
S1 N2 H2A 112(3) . . ?
C13 N3 S1 121.1(3) . . ?
C13 N3 H3A 113(3) . . ?
S1 N3 H3A 111(3) . . ?
C17 N4 C18 121.0(3) . . ?
C17 N4 H4A 120(3) . . ?
C18 N4 H4A 119(3) . . ?
C24 C23 C21 113.1(11) . . ?
C24 C23 H23A 109.0 . . ?
C21 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
C21 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C24' C23' C21 110(2) . . ?
C24' C23' H23C 109.7 . . ?
C21 C23' H23C 109.7 . . ?
C24' C23' H23D 109.7 . . ?
C21 C23' H23D 109.7 . . ?
H23C C23' H23D 108.2 . . ?
C23' C24' H24D 109.5 . . ?
C23' C24' H24E 109.5 . . ?
H24D C24' H24E 109.5 . . ?
C23' C24' H24F 109.5 . . ?
H24D C24' H24F 109.5 . . ?
H24E C24' H24F 109.5 . . ?
C4 C6 C7 113.5(8) . . ?
C4 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
C4 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 N1 -19.8(7) . . . . ?
O2 C2 C3 N1 158.9(4) . . . . ?
O1 C2 C3 C4 102.4(6) . . . . ?
O2 C2 C3 C4 -78.9(6) . . . . ?
N1 C3 C4 C6 -158.2(6) . . . . ?
C2 C3 C4 C6 79.1(8) . . . . ?
N1 C3 C4 C5 75.2(6) . . . . ?
C2 C3 C4 C5 -47.5(6) . . . . ?
O3 C8 C9 N2 -23.9(6) . . . . ?
N1 C8 C9 N2 158.8(4) . . . . ?
O3 C8 C9 C10 100.5(5) . . . . ?
N1 C8 C9 C10 -76.8(5) . . . . ?
N2 C9 C10 C11 61.3(5) . . . . ?
C8 C9 C10 C11 -63.3(5) . . . . ?
N2 C9 C10 C12 -65.0(5) . . . . ?
C8 C9 C10 C12 170.3(4) . . . . ?
N3 C13 C14 C16 61.3(5) . . . . ?
C17 C13 C14 C16 -63.3(5) . . . . ?
N3 C13 C14 C15 -171.8(4) . . . . ?
C17 C13 C14 C15 63.6(6) . . . . ?
N3 C13 C17 O6 150.1(4) . . . . ?
C14 C13 C17 O6 -86.6(5) . . . . ?
N3 C13 C17 N4 -32.7(5) . . . . ?
C14 C13 C17 N4 90.5(5) . . . . ?
N4 C18 C19 O8 129.4(6) . . . . ?
C21 C18 C19 O8 -106.8(6) . . . . ?
N4 C18 C19 O7 -49.9(6) . . . . ?
C21 C18 C19 O7 73.9(5) . . . . ?
N4 C18 C21 C22 170.6(5) . . . . ?
C19 C18 C21 C22 47.1(6) . . . . ?
N4 C18 C21 C23 -69.2(7) . . . . ?
C19 C18 C21 C23 167.3(6) . . . . ?
N4 C18 C21 C23' -46.9(15) . . . . ?
C19 C18 C21 C23' -170.5(15) . . . . ?
O1 C2 O2 C1 -4.9(9) . . . . ?
C3 C2 O2 C1 176.4(6) . . . . ?
O8 C19 O7 C20 0.0(9) . . . . ?
C18 C19 O7 C20 179.4(6) . . . . ?
O3 C8 N1 C3 0.8(7) . . . . ?
C9 C8 N1 C3 178.2(4) . . . . ?
C2 C3 N1 C8 -72.3(5) . . . . ?
C4 C3 N1 C8 164.7(5) . . . . ?
C8 C9 N2 S1 -90.5(4) . . . . ?
C10 C9 N2 S1 143.9(3) . . . . ?
O5 S1 N2 C9 177.6(3) . . . . ?
O4 S1 N2 C9 -52.2(3) . . . . ?
N3 S1 N2 C9 63.2(3) . . . . ?
C17 C13 N3 S1 -68.7(4) . . . . ?
C14 C13 N3 S1 165.9(3) . . . . ?
O5 S1 N3 C13 8.2(4) . . . . ?
O4 S1 N3 C13 -124.0(3) . . . . ?
N2 S1 N3 C13 121.6(3) . . . . ?
O6 C17 N4 C18 -5.2(6) . . . . ?
C13 C17 N4 C18 177.7(4) . . . . ?
C19 C18 N4 C17 -79.3(5) . . . . ?
C21 C18 N4 C17 155.9(4) . . . . ?
C22 C21 C23 C24 -69.9(11) . . . . ?
C18 C21 C23 C24 168.8(9) . . . . ?
C22 C21 C23' C24' 67(5) . . . . ?
C18 C21 C23' C24' -73(5) . . . . ?
C5 C4 C6 C7 -171.5(7) . . . . ?
C3 C4 C6 C7 61.5(9) . . . . ?

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
C1 H1A O4 0.96 2.38 3.230(7) 147.1 4_665
C9 H9 O6 0.98 2.57 3.271(4) 128.1 3_755
C21 H21 O3 0.98 2.48 3.279(5) 139.0 .
N4 H4A O3 0.88(2) 2.07(3) 2.916(4) 160(4) .
N2 H2A O7 0.88(2) 2.32(3) 3.147(5) 155(4) .
N3 H3A O8 0.88(3) 2.08(3) 2.940(5) 166(5) 3_755
N1 H1D O6 0.88(2) 1.99(3) 2.865(5) 173(5) 3_755

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_464
_database_code_depnum_ccdc_archive 'CCDC 1583456'
_audit_update_record             
;
2017-11-01 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H46 N4 O8 S'
_chemical_formula_sum            'C24 H46 N4 O8 S'
_chemical_formula_weight         550.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.5100(9)
_cell_length_b                   15.8715(12)
_cell_length_c                   10.7748(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.503(3)
_cell_angle_gamma                90
_cell_volume                     1567.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3300
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      20.16

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6510
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18505
_diffrn_reflns_av_unetI/netI     0.1105
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.222
_diffrn_reflns_theta_max         26.872
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             18505
_reflns_number_gt                10678
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_max     0.928
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 _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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0391P)²+0.4153P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1021 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         18505
_refine_ls_number_parameters     352
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1276
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1491
_refine_ls_wR_factor_gt          0.1211
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.002
_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 -0.4800(13) 0.1564(9) -0.6515(12) 0.144(6) Uani 1 1 d . . . . .
H1A H -0.5807 0.1401 -0.6796 0.217 Uiso 1 1 calc R U . . .
H1B H -0.4626 0.2023 -0.7035 0.217 Uiso 1 1 calc R U . . .
H1C H -0.4195 0.1095 -0.6598 0.217 Uiso 1 1 calc R U . . .
C2 C -0.3072(12) 0.2071(6) -0.4672(11) 0.060(3) Uani 1 1 d . . . . .
C3 C -0.2910(8) 0.2342(5) -0.3289(9) 0.043(2) Uani 1 1 d . . . . .
H3 H -0.3411 0.1925 -0.2889 0.052 Uiso 1 1 calc R U . . .
C4 C -0.3656(10) 0.3196(6) -0.3256(11) 0.062(3) Uani 1 1 d . . . . .
H4 H -0.4685 0.3135 -0.3731 0.074 Uiso 1 1 calc R U . . .
C5 C -0.3598(11) 0.3413(6) -0.1865(11) 0.083(4) Uani 1 1 d . . . . .
H5A H -0.4017 0.2961 -0.1491 0.124 Uiso 1 1 calc R U . . .
H5B H -0.2601 0.3493 -0.1383 0.124 Uiso 1 1 calc R U . . .
H5C H -0.4138 0.3921 -0.1845 0.124 Uiso 1 1 calc R U . . .
C6 C -0.3003(11) 0.3892(6) -0.3904(12) 0.095(4) Uani 1 1 d . . . . .
H6A H -0.3060 0.3732 -0.4776 0.143 Uiso 1 1 calc R U . . .
H6B H -0.3538 0.4404 -0.3903 0.143 Uiso 1 1 calc R U . . .
H6C H -0.2001 0.3977 -0.3441 0.143 Uiso 1 1 calc R U . . .
C7 C -0.0649(9) 0.1630(5) -0.2259(7) 0.036(2) Uani 1 1 d . . . . .
C8 C 0.0998(9) 0.1715(4) -0.1730(8) 0.040(2) Uani 1 1 d . . . . .
H8 H 0.1208 0.2242 -0.1244 0.049 Uiso 1 1 calc R U . . .
C9 C 0.3258(11) 0.2047(7) -0.2420(12) 0.110(5) Uani 1 1 d . . . . .
H9A H 0.3305 0.2560 -0.1940 0.165 Uiso 1 1 calc R U . . .
H9B H 0.3817 0.1618 -0.1876 0.165 Uiso 1 1 calc R U . . .
H9C H 0.3649 0.2140 -0.3142 0.165 Uiso 1 1 calc R U . . .
C10 C 0.1681(9) 0.1764(5) -0.2897(9) 0.056(3) Uani 1 1 d . . . . .
H10 H 0.1154 0.2203 -0.3476 0.067 Uiso 1 1 calc R U . . .
C11 C 0.1519(11) 0.0946(6) -0.3675(10) 0.075(3) Uani 1 1 d . . . . .
H11A H 0.2174 0.0528 -0.3169 0.090 Uiso 1 1 calc R U . . .
H11B H 0.0531 0.0739 -0.3801 0.090 Uiso 1 1 calc R U . . .
C12 C 0.1827(14) 0.1016(9) -0.4968(12) 0.128(5) Uani 1 1 d . . . . .
H12A H 0.1698 0.0475 -0.5383 0.192 Uiso 1 1 calc R U . . .
H12B H 0.1166 0.1414 -0.5490 0.192 Uiso 1 1 calc R U . . .
H12C H 0.2812 0.1203 -0.4857 0.192 Uiso 1 1 calc R U . . .
C13 C -0.0534(10) 0.0305(4) 0.1345(9) 0.045(2) Uani 1 1 d . . . . .
H13 H 0.0111 0.0231 0.2214 0.054 Uiso 1 1 calc R U . . .
C14 C -0.2080(10) 0.0539(5) 0.1465(10) 0.054(3) Uani 1 1 d . . . . .
H14 H -0.1964 0.1038 0.2017 0.065 Uiso 1 1 calc R U . . .
C15 C -0.3172(10) 0.0770(7) 0.0201(11) 0.084(4) Uani 1 1 d . . . . .
H15A H -0.2770 0.1204 -0.0220 0.127 Uiso 1 1 calc R U . . .
H15B H -0.3381 0.0282 -0.0344 0.127 Uiso 1 1 calc R U . . .
H15C H -0.4057 0.0969 0.0369 0.127 Uiso 1 1 calc R U . . .
C16 C -0.2716(13) -0.0151(6) 0.2137(14) 0.090(4) Uani 1 1 d . . . . .
H16A H -0.3710 0.0003 0.2110 0.107 Uiso 1 1 calc R U . . .
H16B H -0.2760 -0.0667 0.1645 0.107 Uiso 1 1 calc R U . . .
C17 C -0.1914(16) -0.0333(8) 0.3509(15) 0.137(6) Uani 1 1 d . . . . .
H17A H -0.2406 -0.0775 0.3836 0.206 Uiso 1 1 calc R U . . .
H17B H -0.0935 -0.0507 0.3552 0.206 Uiso 1 1 calc R U . . .
H17C H -0.1889 0.0165 0.4019 0.206 Uiso 1 1 calc R U . . .
C18 C -0.0537(8) -0.0514(5) 0.0598(10) 0.040(2) Uani 1 1 d . . . . .
C19 C -0.0829(9) -0.1241(4) -0.1445(8) 0.045(2) Uani 1 1 d . . . . .
H19 H -0.1311 -0.1684 -0.1075 0.054 Uiso 1 1 calc R U . . .
C20 C 0.0699(11) -0.1544(6) -0.1383(10) 0.054(3) Uani 1 1 d . . . . .
C21 C 0.3033(12) -0.1158(7) -0.1625(13) 0.114(5) Uani 1 1 d . . . . .
H21A H 0.3546 -0.0667 -0.1788 0.171 Uiso 1 1 calc R U . . .
H21B H 0.3539 -0.1397 -0.0809 0.171 Uiso 1 1 calc R U . . .
H21C H 0.2987 -0.1565 -0.2294 0.171 Uiso 1 1 calc R U . . .
C22 C -0.1734(12) -0.1099(5) -0.2840(10) 0.064(3) Uani 1 1 d . . . . .
H22 H -0.1331 -0.0612 -0.3186 0.077 Uiso 1 1 calc R U . . .
C23 C -0.1648(13) -0.1870(6) -0.3686(10) 0.098(4) Uani 1 1 d . . . . .
H23A H -0.0646 -0.1985 -0.3647 0.148 Uiso 1 1 calc R U . . .
H23B H -0.2067 -0.2350 -0.3378 0.148 Uiso 1 1 calc R U . . .
H23C H -0.2177 -0.1755 -0.4561 0.148 Uiso 1 1 calc R U . . .
C24 C -0.3300(13) -0.0912(7) -0.2893(13) 0.106(5) Uani 1 1 d . . . . .
H24A H -0.3845 -0.0826 -0.3772 0.159 Uiso 1 1 calc R U . . .
H24B H -0.3707 -0.1378 -0.2539 0.159 Uiso 1 1 calc R U . . .
H24C H -0.3347 -0.0413 -0.2402 0.159 Uiso 1 1 calc R U . . .
N1 N 0.0008(7) 0.1030(5) 0.0736(6) 0.0397(17) Uani 1 1 d D . . . .
N2 N 0.1664(6) 0.1022(5) -0.0884(6) 0.0395(16) Uani 1 1 d D . . . .
N3 N -0.0795(7) -0.0481(4) -0.0671(8) 0.0397(19) Uani 1 1 d D . . . .
N4 N -0.1379(7) 0.2346(4) -0.2575(7) 0.0409(19) Uani 1 1 d D . . . .
O1 O 0.2412(6) 0.0320(3) 0.1207(6) 0.0548(19) Uani 1 1 d . . . . .
O2 O 0.2249(7) 0.1882(3) 0.1059(6) 0.0564(18) Uani 1 1 d . . . . .
O3 O -0.1255(5) 0.0935(3) -0.2412(5) 0.0500(17) Uani 1 1 d . . . . .
O4 O -0.2134(9) 0.2044(6) -0.5202(8) 0.101(3) Uani 1 1 d . . . . .
O5 O -0.4453(7) 0.1827(5) -0.5179(7) 0.093(3) Uani 1 1 d . . . . .
O6 O -0.0335(6) -0.1184(3) 0.1206(6) 0.0536(18) Uani 1 1 d . . . . .
O7 O 0.1099(7) -0.2263(4) -0.1227(7) 0.079(2) Uani 1 1 d . . . . .
O8 O 0.1540(7) -0.0921(3) -0.1601(7) 0.070(2) Uani 1 1 d . . . . .
S1 S 0.1689(2) 0.10681(13) 0.0629(2) 0.0452(6) Uani 1 1 d . . . . .
H2 H 0.141(9) 0.050(3) -0.117(9) 0.08(4) Uiso 1 1 d D . . . .
H3A H -0.103(7) -0.004(3) -0.115(6) 0.03(2) Uiso 1 1 d D . . . .
H4A H -0.091(7) 0.282(3) -0.238(7) 0.03(2) Uiso 1 1 d D . . . .
H1 H -0.035(7) 0.151(3) 0.090(7) 0.03(2) Uiso 1 1 d 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 O5 1.449(12) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O4 1.181(11) . ?
C2 O5 1.338(11) . ?
C2 C3 1.519(13) . ?
C3 N4 1.453(9) . ?
C3 C4 1.534(10) . ?
C3 H3 0.9800 . ?
C4 C6 1.524(13) . ?
C4 C5 1.525(12) . ?
C4 H4 0.9800 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 O3 1.235(8) . ?
C7 N4 1.327(9) . ?
C7 C8 1.523(10) . ?
C8 N2 1.460(9) . ?
C8 C10 1.564(11) . ?
C8 H8 0.9800 . ?
C9 C10 1.517(12) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.531(12) . ?
C10 H10 0.9800 . ?
C11 C12 1.503(12) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N1 1.483(9) . ?
C13 C18 1.529(11) . ?
C13 C14 1.554(11) . ?
C13 H13 0.9800 . ?
C14 C15 1.521(12) . ?
C14 C16 1.524(12) . ?
C14 H14 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.500(16) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O6 1.236(9) . ?
C18 N3 1.324(10) . ?
C19 N3 1.462(9) . ?
C19 C20 1.515(11) . ?
C19 C22 1.537(12) . ?
C19 H19 0.9800 . ?
C20 O7 1.200(10) . ?
C20 O8 1.332(9) . ?
C21 O8 1.476(10) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C24 1.505(12) . ?
C22 C23 1.540(12) . ?
C22 H22 0.9800 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1 S1 1.634(6) . ?
N1 H1 0.88(4) . ?
N2 S1 1.626(7) . ?
N2 H2 0.89(4) . ?
N3 H3A 0.86(4) . ?
N4 H4A 0.87(4) . ?
O1 S1 1.429(5) . ?
O2 S1 1.426(5) . ?

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
O5 C1 H1A 109.5 . . ?
O5 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O5 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O4 C2 O5 125.3(11) . . ?
O4 C2 C3 126.3(9) . . ?
O5 C2 C3 108.3(10) . . ?
N4 C3 C2 110.2(7) . . ?
N4 C3 C4 112.9(7) . . ?
C2 C3 C4 110.3(7) . . ?
N4 C3 H3 107.8 . . ?
C2 C3 H3 107.8 . . ?
C4 C3 H3 107.8 . . ?
C6 C4 C5 112.0(8) . . ?
C6 C4 C3 112.5(8) . . ?
C5 C4 C3 109.1(8) . . ?
C6 C4 H4 107.7 . . ?
C5 C4 H4 107.7 . . ?
C3 C4 H4 107.7 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 N4 122.5(7) . . ?
O3 C7 C8 121.7(7) . . ?
N4 C7 C8 115.8(7) . . ?
N2 C8 C7 113.5(6) . . ?
N2 C8 C10 109.6(6) . . ?
C7 C8 C10 108.1(7) . . ?
N2 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
C10 C8 H8 108.5 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C9 C10 C11 112.5(8) . . ?
C9 C10 C8 109.1(8) . . ?
C11 C10 C8 113.3(7) . . ?
C9 C10 H10 107.2 . . ?
C11 C10 H10 107.2 . . ?
C8 C10 H10 107.2 . . ?
C12 C11 C10 115.4(9) . . ?
C12 C11 H11A 108.4 . . ?
C10 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C10 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C18 112.3(7) . . ?
N1 C13 C14 107.5(6) . . ?
C18 C13 C14 112.2(7) . . ?
N1 C13 H13 108.2 . . ?
C18 C13 H13 108.2 . . ?
C14 C13 H13 108.2 . . ?
C15 C14 C16 109.6(9) . . ?
C15 C14 C13 114.7(8) . . ?
C16 C14 C13 111.9(7) . . ?
C15 C14 H14 106.7 . . ?
C16 C14 H14 106.7 . . ?
C13 C14 H14 106.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C14 116.5(10) . . ?
C17 C16 H16A 108.2 . . ?
C14 C16 H16A 108.2 . . ?
C17 C16 H16B 108.2 . . ?
C14 C16 H16B 108.2 . . ?
H16A C16 H16B 107.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O6 C18 N3 122.8(8) . . ?
O6 C18 C13 118.3(9) . . ?
N3 C18 C13 118.9(7) . . ?
N3 C19 C20 111.2(7) . . ?
N3 C19 C22 111.0(7) . . ?
C20 C19 C22 111.6(8) . . ?
N3 C19 H19 107.6 . . ?
C20 C19 H19 107.6 . . ?
C22 C19 H19 107.6 . . ?
O7 C20 O8 123.2(9) . . ?
O7 C20 C19 124.9(9) . . ?
O8 C20 C19 111.8(8) . . ?
O8 C21 H21A 109.5 . . ?
O8 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O8 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C24 C22 C19 110.8(9) . . ?
C24 C22 C23 110.1(9) . . ?
C19 C22 C23 111.0(8) . . ?
C24 C22 H22 108.3 . . ?
C19 C22 H22 108.3 . . ?
C23 C22 H22 108.3 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C13 N1 S1 121.5(6) . . ?
C13 N1 H1 113(5) . . ?
S1 N1 H1 115(5) . . ?
C8 N2 S1 118.6(6) . . ?
C8 N2 H2 117(6) . . ?
S1 N2 H2 108(6) . . ?
C18 N3 C19 121.7(7) . . ?
C18 N3 H3A 127(5) . . ?
C19 N3 H3A 111(5) . . ?
C7 N4 C3 120.9(6) . . ?
C7 N4 H4A 119(4) . . ?
C3 N4 H4A 120(4) . . ?
C2 O5 C1 115.2(9) . . ?
C20 O8 C21 116.1(7) . . ?
O2 S1 O1 121.1(3) . . ?
O2 S1 N2 105.7(4) . . ?
O1 S1 N2 106.0(4) . . ?
O2 S1 N1 107.4(4) . . ?
O1 S1 N1 107.7(4) . . ?
N2 S1 N1 108.5(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C2 C3 N4 -15.9(13) . . . . ?
O5 C2 C3 N4 161.3(7) . . . . ?
O4 C2 C3 C4 109.3(11) . . . . ?
O5 C2 C3 C4 -73.5(9) . . . . ?
N4 C3 C4 C6 63.4(11) . . . . ?
C2 C3 C4 C6 -60.3(10) . . . . ?
N4 C3 C4 C5 -61.5(10) . . . . ?
C2 C3 C4 C5 174.9(8) . . . . ?
O3 C7 C8 N2 -27.9(11) . . . . ?
N4 C7 C8 N2 153.8(7) . . . . ?
O3 C7 C8 C10 93.8(9) . . . . ?
N4 C7 C8 C10 -84.5(8) . . . . ?
N2 C8 C10 C9 -68.7(9) . . . . ?
C7 C8 C10 C9 167.2(7) . . . . ?
N2 C8 C10 C11 57.4(9) . . . . ?
C7 C8 C10 C11 -66.7(9) . . . . ?
C9 C10 C11 C12 -69.6(12) . . . . ?
C8 C10 C11 C12 166.1(9) . . . . ?
N1 C13 C14 C15 56.9(9) . . . . ?
C18 C13 C14 C15 -67.0(10) . . . . ?
N1 C13 C14 C16 -177.5(8) . . . . ?
C18 C13 C14 C16 58.6(11) . . . . ?
C15 C14 C16 C17 -168.2(10) . . . . ?
C13 C14 C16 C17 63.4(12) . . . . ?
N1 C13 C18 O6 149.0(7) . . . . ?
C14 C13 C18 O6 -89.8(10) . . . . ?
N1 C13 C18 N3 -32.9(11) . . . . ?
C14 C13 C18 N3 88.3(9) . . . . ?
N3 C19 C20 O7 134.8(10) . . . . ?
C22 C19 C20 O7 -100.6(11) . . . . ?
N3 C19 C20 O8 -48.8(11) . . . . ?
C22 C19 C20 O8 75.8(9) . . . . ?
N3 C19 C22 C24 -62.9(10) . . . . ?
C20 C19 C22 C24 172.4(7) . . . . ?
N3 C19 C22 C23 174.5(8) . . . . ?
C20 C19 C22 C23 49.8(11) . . . . ?
C18 C13 N1 S1 -64.5(9) . . . . ?
C14 C13 N1 S1 171.6(6) . . . . ?
C7 C8 N2 S1 -84.7(8) . . . . ?
C10 C8 N2 S1 154.4(5) . . . . ?
O6 C18 N3 C19 -1.3(13) . . . . ?
C13 C18 N3 C19 -179.3(7) . . . . ?
C20 C19 N3 C18 -78.5(10) . . . . ?
C22 C19 N3 C18 156.6(8) . . . . ?
O3 C7 N4 C3 -8.9(12) . . . . ?
C8 C7 N4 C3 169.4(7) . . . . ?
C2 C3 N4 C7 -71.2(9) . . . . ?
C4 C3 N4 C7 165.1(8) . . . . ?
O4 C2 O5 C1 -4.1(16) . . . . ?
C3 C2 O5 C1 178.7(9) . . . . ?
O7 C20 O8 C21 -0.8(15) . . . . ?
C19 C20 O8 C21 -177.2(8) . . . . ?
C8 N2 S1 O2 -49.7(6) . . . . ?
C8 N2 S1 O1 -179.4(6) . . . . ?
C8 N2 S1 N1 65.2(7) . . . . ?
C13 N1 S1 O2 -132.2(6) . . . . ?
C13 N1 S1 O1 -0.3(7) . . . . ?
C13 N1 S1 N2 114.0(6) . . . . ?

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
C1 H1A O2 0.96 2.66 3.323(13) 126.9 1_454
C8 H8 O6 0.98 2.64 3.468(9) 143.0 2
C19 H19 O2 0.98 2.45 3.343(9) 151.8 2_545
C22 H22 O3 0.98 2.59 3.276(10) 127.3 .
N2 H2 O8 0.89(4) 2.31(5) 3.173(9) 161(8) .
N3 H3A O3 0.86(4) 2.04(4) 2.884(9) 170(6) .
N4 H4A O6 0.87(4) 2.17(5) 2.999(8) 159(6) 2
N1 H1 O7 0.88(4) 2.13(4) 3.004(9) 175(6) 2

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.062

