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

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

data_rb89
_database_code_depnum_ccdc_archive 'CCDC 1563706'
_audit_update_record             
;
2017-07-21 deposited with the CCDC.	2019-02-14 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 N2 O6 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         418.45

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.613(3)
_cell_length_b                   15.188(5)
_cell_length_c                   17.464(6)
_cell_angle_alpha                77.323(5)
_cell_angle_beta                 84.333(4)
_cell_angle_gamma                89.849(5)
_cell_volume                     1960.1(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5051
_cell_measurement_theta_min      2.4066
_cell_measurement_theta_max      25.1432
_cell_measurement_temperature    153.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880

_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      153.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            7228
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_theta_min         1.20
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;

Refined as a 2-component twin.
;

_reflns_number_total             7228
_reflns_number_gt                5504
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.0954
_refine_ls_wR_factor_gt          0.2547
_refine_ls_wR_factor_ref         0.2687
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.148
_refine_ls_number_reflns         7228
_refine_ls_number_parameters     528
_refine_ls_number_restraints     60
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1047P)²+7.7136P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.788
_refine_diff_density_min         -0.803
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6110(8) 0.2509(5) 0.1085(4) 0.0193(14) Uani d . . . 1 . .
H H1A 0.6102 0.3177 0.0956 0.023 Uiso calc U . R 1 . .
H H1B 0.5595 0.2284 0.0664 0.023 Uiso calc U . R 1 . .
C C2 0.7999(9) 0.2161(5) 0.1183(4) 0.0237(14) Uani d U . . 1 . .
H H2 0.8883 0.2612 0.0857 0.028 Uiso calc U . R 1 . .
C C3 0.8131(9) 0.2101(5) 0.2062(4) 0.0241(15) Uani d U . . 1 . .
H H3A 0.9057 0.1674 0.2255 0.029 Uiso calc U . R 1 . .
H H3B 0.8416 0.27 0.2158 0.029 Uiso calc U . R 1 . .
C C4 0.6331(8) 0.1765(4) 0.2469(4) 0.0180(14) Uani d . . . 1 . .
H H4 0.6269 0.1091 0.2594 0.022 Uiso calc U . R 1 . .
C C5 0.5918(9) 0.2115(5) 0.3209(4) 0.0244(16) Uani d U . . 1 . .
H H5A 0.5838 0.2782 0.3082 0.029 Uiso calc U . R 1 . .
H H5B 0.4787 0.1854 0.3497 0.029 Uiso calc U . R 1 . .
C C6 0.7046(9) 0.1715(4) 0.4462(4) 0.0161(14) Uani d . . . 1 . .
C C7 0.8646(8) 0.1431(4) 0.4863(4) 0.0156(13) Uani d U . . 1 . .
C C8 0.8532(8) 0.1379(5) 0.5676(4) 0.0167(14) Uani d . . . 1 . .
H H8 0.7459 0.1521 0.5944 0.02 Uiso calc U . R 1 . .
C C9 0.9970(9) 0.1121(5) 0.6091(4) 0.0247(16) Uani d . . . 1 . .
H H9 0.991 0.1101 0.6641 0.03 Uiso calc U . R 1 . .
C C10 1.1509(9) 0.0891(5) 0.5686(4) 0.0258(16) Uani d . . . 1 . .
C C11 1.1648(8) 0.0943(4) 0.4889(4) 0.0190(14) Uani d . . . 1 . .
H H11 1.2723 0.0799 0.4623 0.023 Uiso calc U . R 1 . .
C C12 1.0228(9) 0.1205(4) 0.4482(4) 0.0179(14) Uani d . . . 1 . .
H H12 1.0315 0.1234 0.393 0.021 Uiso calc U . R 1 . .
C C13 0.8253(11) 0.1246(6) 0.0964(6) 0.035(2) Uani d . . . 1 . .
H H13A 0.7373 0.0812 0.1282 0.052 Uiso calc U . R 1 . .
H H13B 0.944 0.1031 0.1066 0.052 Uiso calc U . R 1 . .
H H13C 0.8107 0.1308 0.0403 0.052 Uiso calc U . R 1 . .
C C14 0.3357(8) 0.0606(4) 0.1741(4) 0.0162(13) Uani d . . . 1 . .
C C15 0.3467(10) -0.0129(5) 0.2362(4) 0.0254(16) Uani d . . . 1 . .
H H15 0.3453 -0.0049 0.2887 0.031 Uiso calc U . R 1 . .
C C16 0.3597(10) -0.0984(5) 0.2204(5) 0.0274(17) Uani d . . . 1 . .
H H16 0.3686 -0.1487 0.2631 0.033 Uiso calc U . R 1 . .
C C17 0.3603(9) -0.1134(5) 0.1457(4) 0.0226(15) Uani d . . . 1 . .
C C18 0.3713(10) -0.2091(5) 0.1315(5) 0.0323(18) Uani d . . . 1 . .
H H18A 0.4809 -0.2365 0.1495 0.048 Uiso calc U . R 1 . .
H H18B 0.37 -0.2069 0.0751 0.048 Uiso calc U . R 1 . .
H H18C 0.2701 -0.2453 0.161 0.048 Uiso calc U . R 1 . .
C C19 0.3497(10) -0.0394(5) 0.0842(4) 0.0241(16) Uani d . . . 1 . .
H H19 0.3509 -0.0484 0.032 0.029 Uiso calc U . R 1 . .
C C20 0.3373(9) 0.0480(5) 0.0968(4) 0.0207(16) Uani d . . . 1 . .
H H20 0.33 0.0981 0.0539 0.025 Uiso calc U . R 1 . .
C C21 0.1177(9) 0.4446(5) 0.1060(4) 0.0274(16) Uani d . . . 1 . .
H H21A 0.0622 0.486 0.0635 0.033 Uiso calc U . R 1 . .
H H21B 0.121 0.3835 0.0947 0.033 Uiso calc U . R 1 . .
C C22 0.3022(10) 0.4780(5) 0.1123(4) 0.0246(16) Uani d . . . 1 . .
H H22 0.391 0.4503 0.079 0.03 Uiso calc U . R 1 . .
C C23 0.3238(9) 0.4419(5) 0.1999(4) 0.0239(16) Uani d U . . 1 . .
H H23A 0.4153 0.4772 0.2173 0.029 Uiso calc U . R 1 . .
H H23B 0.3574 0.3777 0.21 0.029 Uiso calc U . R 1 . .
C C24 0.1395(8) 0.4529(4) 0.2436(4) 0.0162(13) Uani d . . . 1 . .
H H24 0.1296 0.5142 0.2557 0.019 Uiso calc U . R 1 . .
C C25 0.1004(9) 0.3796(5) 0.3187(4) 0.0252(16) Uani d . . . 1 . .
H H25A -0.0143 0.3899 0.3471 0.03 Uiso calc U . R 1 . .
H H25B 0.097 0.3192 0.3061 0.03 Uiso calc U . R 1 . .
C C26 0.2095(9) 0.3557(5) 0.4444(4) 0.0215(16) Uani d . . . 1 . .
C C27 0.3683(8) 0.3666(4) 0.4866(4) 0.0126(12) Uani d . . . 1 . .
C C28 0.3521(10) 0.3324(5) 0.5679(4) 0.0229(16) Uani d . . . 1 . .
H H28 0.2432 0.3068 0.5946 0.027 Uiso calc U . R 1 . .
C C29 0.4958(10) 0.3364(5) 0.6090(4) 0.0266(16) Uani d . . . 1 . .
H H29 0.4886 0.312 0.6642 0.032 Uiso calc U . R 1 . .
C C30 0.6493(9) 0.3760(4) 0.5691(4) 0.0171(14) Uani d . . . 1 . .
C C31 0.6716(9) 0.4137(4) 0.4886(4) 0.0203(13) Uani d U . . 1 . .
H H31 0.7787 0.4429 0.4633 0.024 Uiso calc U . R 1 . .
C C32 0.5246(8) 0.4058(4) 0.4468(4) 0.0187(13) Uani d U . . 1 . .
H H32 0.5333 0.4274 0.3912 0.022 Uiso calc U . R 1 . .
C C33 0.3187(12) 0.5796(6) 0.0891(6) 0.040(2) Uani d . . . 1 . .
H H33A 0.2297 0.606 0.1213 0.059 Uiso calc U . R 1 . .
H H33B 0.3005 0.6001 0.0333 0.059 Uiso calc U . R 1 . .
H H33C 0.4368 0.5986 0.0977 0.059 Uiso calc U . R 1 . .
C C34 -0.1659(9) 0.6018(5) 0.1658(4) 0.0178(14) Uani d U . . 1 . .
C C35 -0.1644(10) 0.6500(5) 0.0897(5) 0.0244(17) Uani d . . . 1 . .
H H35 -0.171 0.6191 0.0483 0.029 Uiso calc U . R 1 . .
C C36 -0.1533(10) 0.7436(5) 0.0724(5) 0.0265(16) Uani d . . . 1 . .
H H36 -0.155 0.7768 0.0197 0.032 Uiso calc U . R 1 . .
C C37 -0.1395(9) 0.7890(5) 0.1339(5) 0.0284(17) Uani d . . . 1 . .
C C38 -0.1383(11) 0.7400(5) 0.2100(5) 0.0307(18) Uani d . . . 1 . .
H H38 -0.1288 0.771 0.2512 0.037 Uiso calc U . R 1 . .
C C39 -0.1507(9) 0.6451(5) 0.2285(4) 0.0216(15) Uani d . . . 1 . .
H H39 -0.149 0.6116 0.2812 0.026 Uiso calc U . R 1 . .
C C40 -0.1345(11) 0.8921(5) 0.1166(6) 0.038(2) Uani d . . . 1 . .
H H40A -0.1122 0.9123 0.1644 0.058 Uiso calc U . R 1 . .
H H40B -0.2481 0.9151 0.0996 0.058 Uiso calc U . R 1 . .
H H40C -0.0401 0.9151 0.0746 0.058 Uiso calc U . R 1 . .
N N1 0.5123(7) 0.2138(4) 0.1868(3) 0.0156(11) Uani d . . . 1 . .
N N2 1.3027(8) 0.0620(4) 0.6134(4) 0.0285(14) Uani d . . . 1 . .
N N3 0.0194(7) 0.4431(4) 0.1839(3) 0.0167(12) Uani d . . . 1 . .
N N4 0.8026(8) 0.3822(4) 0.6137(4) 0.0280(14) Uani d . . . 1 . .
O O1 0.2393(6) 0.1609(3) 0.2709(3) 0.0202(10) Uani d . . . 1 . .
O O2 0.2346(6) 0.2240(3) 0.1275(3) 0.0249(11) Uani d . . . 1 . .
O O3 0.7384(6) 0.1830(4) 0.3678(3) 0.0237(11) Uani d . . . 1 . .
O O4 0.5645(6) 0.1860(3) 0.4784(3) 0.0235(11) Uani d . . . 1 . .
O O5 1.4119(7) 0.0146(4) 0.5874(3) 0.0336(13) Uani d . . . 1 . .
O O6 1.3088(9) 0.0857(6) 0.6756(4) 0.063(2) Uani d . . . 1 . .
O O7 -0.2622(6) 0.4583(3) 0.1233(3) 0.0286(12) Uani d . . . 1 . .
O O8 -0.2567(6) 0.4549(3) 0.2672(3) 0.0270(12) Uani d . . . 1 . .
O O9 0.2439(6) 0.3871(4) 0.3654(3) 0.0251(11) Uani d . . . 1 . .
O O10 0.0692(6) 0.3263(3) 0.4764(3) 0.0257(11) Uani d . . . 1 . .
O O11 0.9152(7) 0.4416(4) 0.5867(3) 0.0351(13) Uani d . . . 1 . .
O O12 0.8101(9) 0.3272(5) 0.6753(4) 0.060(2) Uani d . . . 1 . .
S S1 0.3169(2) 0.17061(11) 0.19114(10) 0.0167(4) Uani d . . . 1 . .
S S2 -0.1795(2) 0.48308(11) 0.18731(10) 0.0187(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.487(8) ?
C1 C2 . 1.544(9) ?
C2 C13 . 1.527(11) ?
C2 C3 . 1.531(10) ?
C3 C4 . 1.515(10) ?
C4 N1 . 1.481(8) ?
C4 C5 . 1.508(10) ?
C5 O3 . 1.458(7) ?
C6 O4 . 1.199(8) ?
C6 O3 . 1.340(8) ?
C6 C7 . 1.482(9) ?
C7 C12 . 1.397(9) ?
C7 C8 . 1.398(9) ?
C8 C9 . 1.381(9) ?
C9 C10 . 1.392(10) ?
C10 C11 . 1.371(10) ?
C10 N2 . 1.467(9) ?
C11 C12 . 1.363(9) ?
C14 C15 . 1.384(10) ?
C14 C20 . 1.402(10) ?
C14 S1 . 1.763(7) ?
C15 C16 . 1.387(10) ?
C16 C17 . 1.373(10) ?
C17 C19 . 1.382(10) ?
C17 C18 . 1.529(10) ?
C19 C20 . 1.395(11) ?
C21 N3 . 1.483(9) ?
C21 C22 . 1.517(10) ?
C22 C33 . 1.509(11) ?
C22 C23 . 1.532(10) ?
C23 C24 . 1.556(9) ?
C24 N3 . 1.485(7) ?
C24 C25 . 1.526(9) ?
C25 O9 . 1.446(7) ?
C26 O10 . 1.195(9) ?
C26 O9 . 1.356(8) ?
C26 C27 . 1.504(9) ?
C27 C32 . 1.383(9) ?
C27 C28 . 1.394(9) ?
C28 C29 . 1.374(10) ?
C29 C30 . 1.368(10) ?
C30 C31 . 1.391(9) ?
C30 N4 . 1.480(8) ?
C31 C32 . 1.414(9) ?
C34 C35 . 1.369(10) ?
C34 C39 . 1.409(9) ?
C34 S2 . 1.761(7) ?
C35 C36 . 1.388(11) ?
C36 C37 . 1.410(11) ?
C37 C38 . 1.374(11) ?
C37 C40 . 1.528(10) ?
C38 C39 . 1.407(10) ?
N1 S1 . 1.616(5) ?
N2 O5 . 1.217(8) ?
N2 O6 . 1.220(8) ?
N3 S2 . 1.631(5) ?
N4 O12 . 1.214(8) ?
N4 O11 . 1.228(8) ?
O1 S1 . 1.435(5) ?
O2 S1 . 1.423(5) ?
O7 S2 . 1.454(5) ?
O8 S2 . 1.433(5) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 103.8(5) ?
C13 C2 C3 . . 112.0(7) ?
C13 C2 C1 . . 112.0(6) ?
C3 C2 C1 . . 102.0(6) ?
C4 C3 C2 . . 105.4(6) ?
N1 C4 C5 . . 111.4(5) ?
N1 C4 C3 . . 103.0(5) ?
C5 C4 C3 . . 111.0(6) ?
O3 C5 C4 . . 105.0(5) ?
O4 C6 O3 . . 123.8(6) ?
O4 C6 C7 . . 125.1(6) ?
O3 C6 C7 . . 111.0(6) ?
C12 C7 C8 . . 118.9(6) ?
C12 C7 C6 . . 124.0(6) ?
C8 C7 C6 . . 117.0(6) ?
C9 C8 C7 . . 120.4(6) ?
C8 C9 C10 . . 118.5(6) ?
C11 C10 C9 . . 121.9(6) ?
C11 C10 N2 . . 120.2(7) ?
C9 C10 N2 . . 117.9(6) ?
C12 C11 C10 . . 119.3(6) ?
C11 C12 C7 . . 120.9(6) ?
C15 C14 C20 . . 120.1(6) ?
C15 C14 S1 . . 120.6(5) ?
C20 C14 S1 . . 119.3(5) ?
C14 C15 C16 . . 118.8(7) ?
C17 C16 C15 . . 122.7(7) ?
C16 C17 C19 . . 118.0(7) ?
C16 C17 C18 . . 120.7(7) ?
C19 C17 C18 . . 121.3(7) ?
C17 C19 C20 . . 121.6(7) ?
C19 C20 C14 . . 118.8(7) ?
N3 C21 C22 . . 105.0(6) ?
C33 C22 C21 . . 112.0(6) ?
C33 C22 C23 . . 112.0(7) ?
C21 C22 C23 . . 102.2(6) ?
C22 C23 C24 . . 104.9(5) ?
N3 C24 C25 . . 110.7(5) ?
N3 C24 C23 . . 101.8(5) ?
C25 C24 C23 . . 112.1(6) ?
O9 C25 C24 . . 104.8(5) ?
O10 C26 O9 . . 124.2(6) ?
O10 C26 C27 . . 124.5(6) ?
O9 C26 C27 . . 111.2(6) ?
C32 C27 C28 . . 121.4(6) ?
C32 C27 C26 . . 122.0(6) ?
C28 C27 C26 . . 116.6(6) ?
C29 C28 C27 . . 119.1(7) ?
C30 C29 C28 . . 119.0(6) ?
C29 C30 C31 . . 124.5(6) ?
C29 C30 N4 . . 118.9(6) ?
C31 C30 N4 . . 116.6(6) ?
C30 C31 C32 . . 115.8(6) ?
C27 C32 C31 . . 120.2(6) ?
C35 C34 C39 . . 121.4(7) ?
C35 C34 S2 . . 120.4(6) ?
C39 C34 S2 . . 118.3(5) ?
C34 C35 C36 . . 120.6(8) ?
C35 C36 C37 . . 119.4(7) ?
C38 C37 C36 . . 119.5(7) ?
C38 C37 C40 . . 120.2(7) ?
C36 C37 C40 . . 120.2(7) ?
C37 C38 C39 . . 121.7(7) ?
C38 C39 C34 . . 117.4(7) ?
C4 N1 C1 . . 111.6(5) ?
C4 N1 S1 . . 120.7(4) ?
C1 N1 S1 . . 119.4(4) ?
O5 N2 O6 . . 124.1(6) ?
O5 N2 C10 . . 117.6(6) ?
O6 N2 C10 . . 118.2(6) ?
C21 N3 C24 . . 111.8(5) ?
C21 N3 S2 . . 119.0(4) ?
C24 N3 S2 . . 120.8(4) ?
O12 N4 O11 . . 123.6(6) ?
O12 N4 C30 . . 117.5(6) ?
O11 N4 C30 . . 118.9(6) ?
C6 O3 C5 . . 116.7(5) ?
C26 O9 C25 . . 116.1(5) ?
O2 S1 O1 . . 120.5(3) ?
O2 S1 N1 . . 106.3(3) ?
O1 S1 N1 . . 106.8(3) ?
O2 S1 C14 . . 107.5(3) ?
O1 S1 C14 . . 106.4(3) ?
N1 S1 C14 . . 109.0(3) ?
O8 S2 O7 . . 120.6(3) ?
O8 S2 N3 . . 107.0(3) ?
O7 S2 N3 . . 106.4(3) ?
O8 S2 C34 . . 106.9(3) ?
O7 S2 C34 . . 106.5(3) ?
N3 S2 C34 . . 109.1(3) ?


# start Validation Reply Form
_vrf_PLAT340_rb89                
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01018 Ang.  
RESPONSE: This is probably due to twinning.
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane, hexane'
####################################################################### 
# 
# 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_rb93
_database_code_depnum_ccdc_archive 'CCDC 1563707'
_audit_update_record             
;
2017-07-21 deposited with the CCDC.	2019-02-14 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H24 N2 O6 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         432.48

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5182(15)
_cell_length_b                   9.9604(15)
_cell_length_c                   10.7803(17)
_cell_angle_alpha                89.926(4)
_cell_angle_beta                 89.896(4)
_cell_angle_gamma                89.878(4)
_cell_volume                     1022.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9177
_cell_measurement_theta_min      2.7825
_cell_measurement_theta_max      29.4280
_cell_measurement_temperature    223.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456

_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      223.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            49336
_diffrn_reflns_av_R_equivalents  0.1142
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         29.43
_diffrn_reflns_theta_full        29.43
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;

Refined as a 2-component twin.
;

_reflns_number_total             5546
_reflns_number_gt                4827
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_gt          0.1522
_refine_ls_wR_factor_ref         0.1637
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_restrained_S_all      0.947
_refine_ls_number_reflns         5546
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+1.2595P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.566
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.8400(3) 0.4329(3) 0.6372(3) 0.0204(6) Uani d . . . 1 . .
H H1A 0.7383 0.4347 0.623 0.024 Uiso calc U . R 1 . .
H H1B 0.8844 0.3865 0.5673 0.024 Uiso calc U . R 1 . .
C C2 0.8953(3) 0.5758(3) 0.6454(3) 0.0215(6) Uani d . . . 1 . .
H H2A 0.867 0.6259 0.5712 0.026 Uiso calc U . R 1 . .
H H2B 0.9982 0.5739 0.6481 0.026 Uiso calc U . R 1 . .
C C3 0.8387(3) 0.6469(3) 0.7613(3) 0.0249(6) Uani d . . . 1 . .
H H3 0.7353 0.6527 0.7532 0.03 Uiso calc U . R 1 . .
C C4 0.8946(3) 0.7901(3) 0.7702(3) 0.0275(7) Uani d . . . 1 . .
H H4A 0.8579 0.8324 0.8445 0.041 Uiso calc U . R 1 . .
H H4B 0.8651 0.8408 0.6979 0.041 Uiso calc U . R 1 . .
H H4C 0.9964 0.788 0.7739 0.041 Uiso calc U . R 1 . .
C C5 0.8701(3) 0.5659(3) 0.8765(3) 0.0209(6) Uani d . . . 1 . .
H H5A 0.8251 0.6095 0.9478 0.025 Uiso calc U . R 1 . .
H H5B 0.9717 0.5664 0.8908 0.025 Uiso calc U . R 1 . .
C C6 0.8198(3) 0.4198(3) 0.8696(3) 0.0176(5) Uani d . . . 1 . .
H H6 0.8616 0.3695 0.9397 0.021 Uiso calc U . R 1 . .
C C7 0.6599(3) 0.4145(3) 0.8822(3) 0.0197(5) Uani d . . . 1 . .
H H7A 0.6313 0.4452 0.9648 0.024 Uiso calc U . R 1 . .
H H7B 0.6159 0.4729 0.8201 0.024 Uiso calc U . R 1 . .
C C8 0.4878(3) 0.2448(3) 0.9036(3) 0.0165(5) Uani d . . . 1 . .
C C9 0.4506(3) 0.1031(2) 0.8729(2) 0.0156(5) Uani d . . . 1 . .
C C10 0.5483(3) 0.0180(3) 0.8167(3) 0.0174(5) Uani d . . . 1 . .
H H10 0.6383 0.0497 0.7961 0.021 Uiso calc U . R 1 . .
C C11 0.5114(3) -0.1137(3) 0.7917(3) 0.0190(5) Uani d . . . 1 . .
H H11 0.5755 -0.1726 0.7535 0.023 Uiso calc U . R 1 . .
C C12 0.3781(3) -0.1567(3) 0.8241(2) 0.0165(5) Uani d . . . 1 . .
C C13 0.2785(3) -0.0746(3) 0.8799(3) 0.0187(5) Uani d . . . 1 . .
H H13 0.189 -0.1072 0.901 0.022 Uiso calc U . R 1 . .
C C14 0.3161(3) 0.0577(3) 0.9033(3) 0.0174(5) Uani d . . . 1 . .
H H14 0.2509 0.1168 0.9397 0.021 Uiso calc U . R 1 . .
C C15 1.0914(3) 0.2165(3) 0.6784(3) 0.0168(5) Uani d . . . 1 . .
C C16 1.1359(3) 0.1129(3) 0.6010(3) 0.0197(5) Uani d . . . 1 . .
H H16 1.075 0.0419 0.5817 0.024 Uiso calc U . R 1 . .
C C17 1.2722(3) 0.1155(3) 0.5525(3) 0.0216(6) Uani d . . . 1 . .
H H17 1.3025 0.0455 0.5006 0.026 Uiso calc U . R 1 . .
C C18 1.3637(3) 0.2203(3) 0.5799(3) 0.0199(5) Uani d . . . 1 . .
C C19 1.5122(3) 0.2220(3) 0.5308(3) 0.0275(6) Uani d . . . 1 . .
H H19A 1.5245 0.1496 0.4716 0.041 Uiso calc U . R 1 . .
H H19B 1.5775 0.2102 0.5989 0.041 Uiso calc U . R 1 . .
H H19C 1.5301 0.3072 0.4902 0.041 Uiso calc U . R 1 . .
C C20 1.3158(3) 0.3239(3) 0.6564(3) 0.0193(5) Uani d . . . 1 . .
H H20 1.3757 0.3962 0.674 0.023 Uiso calc U . R 1 . .
C C21 1.1814(3) 0.3223(3) 0.7070(3) 0.0185(5) Uani d . . . 1 . .
H H21 1.1515 0.3917 0.7599 0.022 Uiso calc U . R 1 . .
N N1 0.8706(2) 0.3604(2) 0.7535(3) 0.0180(4) Uani d . . . 1 . .
N N2 0.3415(3) -0.2976(2) 0.7988(2) 0.0198(5) Uani d . . . 1 . .
O O1 0.6167(2) 0.27637(18) 0.8635(2) 0.0201(4) Uani d . . . 1 . .
O O2 0.4110(2) 0.3206(2) 0.9588(2) 0.0235(4) Uani d . . . 1 . .
O O3 0.9359(2) 0.1565(2) 0.8706(2) 0.0271(5) Uani d . . . 1 . .
O O4 0.8385(2) 0.1304(2) 0.6601(2) 0.0268(5) Uani d . . . 1 . .
O O5 0.2264(3) -0.3386(2) 0.8315(2) 0.0312(5) Uani d . . . 1 . .
O O6 0.4296(2) -0.36719(19) 0.7448(3) 0.0278(5) Uani d . . . 1 . .
S S1 0.92250(7) 0.20562(6) 0.74570(7) 0.01882(16) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.475(4) ?
C1 C2 . 1.521(4) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C2 C3 . 1.534(4) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C3 C5 . 1.509(4) ?
C3 C4 . 1.526(4) ?
C3 H3 . 0.99 ?
C4 H4A . 0.97 ?
C4 H4B . 0.97 ?
C4 H4C . 0.97 ?
C5 C6 . 1.535(4) ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C6 N1 . 1.466(4) ?
C6 C7 . 1.528(4) ?
C6 H6 . 0.99 ?
C7 O1 . 1.451(3) ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C8 O2 . 1.207(3) ?
C8 O1 . 1.338(3) ?
C8 C9 . 1.494(3) ?
C9 C10 . 1.394(4) ?
C9 C14 . 1.397(4) ?
C10 C11 . 1.386(4) ?
C10 H10 . 0.94 ?
C11 C12 . 1.384(4) ?
C11 H11 . 0.94 ?
C12 C13 . 1.387(4) ?
C12 N2 . 1.473(3) ?
C13 C14 . 1.390(4) ?
C13 H13 . 0.94 ?
C14 H14 . 0.94 ?
C15 C16 . 1.392(4) ?
C15 C21 . 1.394(4) ?
C15 S1 . 1.766(3) ?
C16 C17 . 1.397(4) ?
C16 H16 . 0.94 ?
C17 C18 . 1.393(4) ?
C17 H17 . 0.94 ?
C18 C20 . 1.397(4) ?
C18 C19 . 1.509(4) ?
C19 H19A . 0.97 ?
C19 H19B . 0.97 ?
C19 H19C . 0.97 ?
C20 C21 . 1.390(4) ?
C20 H20 . 0.94 ?
C21 H21 . 0.94 ?
N1 S1 . 1.620(2) ?
N2 O5 . 1.221(3) ?
N2 O6 . 1.233(3) ?
O3 S1 . 1.437(2) ?
O4 S1 . 1.435(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 109.8(2) ?
N1 C1 H1A . . 109.7 ?
C2 C1 H1A . . 109.7 ?
N1 C1 H1B . . 109.7 ?
C2 C1 H1B . . 109.7 ?
H1A C1 H1B . . 108.2 ?
C1 C2 C3 . . 111.0(2) ?
C1 C2 H2A . . 109.4 ?
C3 C2 H2A . . 109.4 ?
C1 C2 H2B . . 109.4 ?
C3 C2 H2B . . 109.4 ?
H2A C2 H2B . . 108.0 ?
C5 C3 C4 . . 112.2(3) ?
C5 C3 C2 . . 110.7(2) ?
C4 C3 C2 . . 111.2(3) ?
C5 C3 H3 . . 107.5 ?
C4 C3 H3 . . 107.5 ?
C2 C3 H3 . . 107.5 ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C3 C5 C6 . . 113.8(2) ?
C3 C5 H5A . . 108.8 ?
C6 C5 H5A . . 108.8 ?
C3 C5 H5B . . 108.8 ?
C6 C5 H5B . . 108.8 ?
H5A C5 H5B . . 107.7 ?
N1 C6 C7 . . 112.9(2) ?
N1 C6 C5 . . 108.8(2) ?
C7 C6 C5 . . 109.9(2) ?
N1 C6 H6 . . 108.4 ?
C7 C6 H6 . . 108.4 ?
C5 C6 H6 . . 108.4 ?
O1 C7 C6 . . 107.7(2) ?
O1 C7 H7A . . 110.2 ?
C6 C7 H7A . . 110.2 ?
O1 C7 H7B . . 110.2 ?
C6 C7 H7B . . 110.2 ?
H7A C7 H7B . . 108.5 ?
O2 C8 O1 . . 124.5(2) ?
O2 C8 C9 . . 123.8(3) ?
O1 C8 C9 . . 111.7(2) ?
C10 C9 C14 . . 121.0(2) ?
C10 C9 C8 . . 120.8(2) ?
C14 C9 C8 . . 118.2(2) ?
C11 C10 C9 . . 119.4(3) ?
C11 C10 H10 . . 120.3 ?
C9 C10 H10 . . 120.3 ?
C12 C11 C10 . . 118.6(2) ?
C12 C11 H11 . . 120.7 ?
C10 C11 H11 . . 120.7 ?
C11 C12 C13 . . 123.5(2) ?
C11 C12 N2 . . 117.8(2) ?
C13 C12 N2 . . 118.7(2) ?
C12 C13 C14 . . 117.5(3) ?
C12 C13 H13 . . 121.3 ?
C14 C13 H13 . . 121.3 ?
C13 C14 C9 . . 120.1(2) ?
C13 C14 H14 . . 119.9 ?
C9 C14 H14 . . 119.9 ?
C16 C15 C21 . . 120.5(3) ?
C16 C15 S1 . . 118.4(2) ?
C21 C15 S1 . . 121.0(2) ?
C15 C16 C17 . . 119.4(2) ?
C15 C16 H16 . . 120.3 ?
C17 C16 H16 . . 120.3 ?
C18 C17 C16 . . 121.1(3) ?
C18 C17 H17 . . 119.5 ?
C16 C17 H17 . . 119.5 ?
C17 C18 C20 . . 118.4(3) ?
C17 C18 C19 . . 121.4(3) ?
C20 C18 C19 . . 120.2(3) ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C21 C20 C18 . . 121.4(3) ?
C21 C20 H20 . . 119.3 ?
C18 C20 H20 . . 119.3 ?
C20 C21 C15 . . 119.2(3) ?
C20 C21 H21 . . 120.4 ?
C15 C21 H21 . . 120.4 ?
C6 N1 C1 . . 117.6(2) ?
C6 N1 S1 . . 121.89(19) ?
C1 N1 S1 . . 118.8(2) ?
O5 N2 O6 . . 123.8(2) ?
O5 N2 C12 . . 118.7(2) ?
O6 N2 C12 . . 117.5(2) ?
C8 O1 C7 . . 116.0(2) ?
O4 S1 O3 . . 118.35(14) ?
O4 S1 N1 . . 111.18(13) ?
O3 S1 N1 . . 107.57(14) ?
O4 S1 C15 . . 106.07(13) ?
O3 S1 C15 . . 108.88(14) ?
N1 S1 C15 . . 103.81(12) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane-hexane'
