# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_sc01s
_database_code_depnum_ccdc_archive 'CCDC 1487568'
_audit_update_record             
;
2016-06-24 deposited with the CCDC.
2016-08-26 downloaded from the CCDC.
;

_audit_creation_date             2016-05-25
_audit_creation_method           SHELXL-2014
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#------------------ Validation  reply form ----------------------------------#
_vrf_PLAT213_sc01s               
;
PROBLEM: Atom C20A            has ADP max/min Ratio .....        3.4 prolat
RESPONSE: Atoms O4, C19 and C20 belong to disordered etoxy moieties. Low-T 
experiments are required to assess the nature of the disorder and to provide
a better description of these terminal groups.
;
_vrf_PLAT220_sc01s               
;
PROBLEM: Non-Solvent Resd 1   C   Ueq(max)/Ueq(min) Range        3.5 Ratio 
RESPONSE: Atoms O4, C19 and C20 belong to disordered etoxy moieties. As 
expected, these terminal groups show apparently larger Ueq parameters. 
Low-T experiments are required to assess the nature of the disorder and to 
provide a better description of these terminal groups.
;
_vrf_PLAT230_sc01s               
;
PROBLEM: Hirshfeld Test Diff for    S1     --  O1      ..        5.3 s.u.  
RESPONSE: This experiment was carried out at room temperature on a twinned
specimen and the asymmetric unit is partially disordered. A sample of 
better quality, in conjunction with low-T experiments, are required
to provide a more accurate description of the S1-O1 distance.
;
_vrf_PLAT241_sc01s               
;
PROBLEM:High   'MainMol' Ueq as Compared to Neighbors of        C16 Check 
RESPONSE: This atom belongs to the phenyl ring of the terminal benzyl moiety, 
which likely undergoes significant in-plane rigid libration motion. Low-T 
experiments are required to provide a better description of the internal 
dynamics of this molecule.
;
_vrf_PLAT242_sc01s               
;
PROBLEM:Low    'MainMol' Ueq as Compared to Neighbors of        C12 Check 
PROBLEM:Low    'MainMol' Ueq as Compared to Neighbors of        C19 Check 
PROBLEM:Low    'MainMol' Ueq as Compared to Neighbors of        C22 Check 
RESPONSE: C12 belongs to the terminal phenyl ring, connecting the latter 
with the benzylic methylene. The phenyl undergoes significant in-plane
libration and, on average, it is expected to bear higher Ueq than C12.
C19 is an ester carbon in close proximity with disordered etoxy groups.
C22 is the quaternary atom of a t-butyl substituent; therefore, it is
expected to undergo be subject to lower thermal motion than its neghbours. 
In any case, low-T experiments are required to provide a better 
description of the internal dynamics of this molecule.
;
_vrf_PLAT340_sc01s               
;
PROBLEM:Low Bond Precision on  C-C Bonds ...............     0.0055 Ang.  
RESPONSE: The sample employed in this study suffer by partial twinning. 
The minor lattice component is rotated by roughly 142 deg around the 
[0.4, 1.0, -0.6] real direction. Roughly the 45 % of the reflections, 
mainly the low-order ones, suffer a maximum of roughly 5 % of intensity 
contamination due to the minority component (TWINABS and SHELX estimates).
Moreover, some groups in the asymmetric unit are disordered. A sample of 
better quality, in conjunction with low-T experiments, are required
to provide a more precise description of the geometrical parameters.
;

#------------------ CHEMICAL INFORMATION ------------------------------------#
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H28 N2 O4 S'
_chemical_formula_sum            'C25 H28 N2 O4 S'
_chemical_formula_weight         452.55

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

_cell_length_a                   8.78200(10)
_cell_length_b                   10.8274(2)
_cell_length_c                   26.0299(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2475.09(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9954
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      20.80

_exptl_crystal_description       Prism
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   0.973
_exptl_transmission_factor_max   1.000
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.163
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   twinabs
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS APEX CCD area-detector'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29165
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.565
_diffrn_reflns_theta_max         27.597
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             29165
_reflns_number_gt                23117
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    1.000

_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.
 The sample was twinned. The model accounts for intensity 
 contamination (less than 5 %) of the collected reflections 
 through the BASF parameter. 
;

_computing_data_collection       'SAINT+ (Bruker AXS, Madison (USA) 1994-1996)'
_computing_cell_refinement       'SAINT+ (Bruker AXS, Madison (USA) 1994-1996)'
_computing_data_reduction        'SAINT+ (Bruker AXS, Madison (USA) 1994-1996)'
_computing_structure_solution    'SHELXS-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/4 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond v3.2i (Brandenburg, 2012)'
_computing_publication_material  ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0552P)²+0.0523P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1511 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         29165
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.72909(9) 0.04997(7) 0.15850(3) 0.0693(2) Uani 1 1 d . . . . .
N1 N 0.6151(3) 0.0680(2) 0.10540(7) 0.0651(6) Uani 1 1 d . . . . .
N2 N 0.7042(3) 0.3821(2) 0.08744(9) 0.0717(6) Uani 1 1 d . . . . .
O1 O 0.8314(2) -0.0547(2) 0.14902(7) 0.0842(6) Uani 1 1 d . . . . .
O2 O 0.8760(3) 0.2301(2) 0.06692(9) 0.0948(7) Uani 1 1 d . . . . .
O3 O 0.5634(3) -0.1274(2) -0.03333(8) 0.0985(8) Uani 1 1 d . . . . .
C1 C 0.6089(3) -0.0083(3) 0.06188(10) 0.0647(7) Uani 1 1 d . . . . .
C2 C 0.5832(4) 0.1010(2) 0.02720(10) 0.0760(8) Uani 1 1 d . . . . .
H2A H 0.4822 0.1040 0.0121 0.091 Uiso 1 1 calc R U . . .
H2B H 0.6613 0.1118 0.0013 0.091 Uiso 1 1 calc R U . . .
C3 C 0.6030(3) 0.1858(3) 0.07500(10) 0.0668(7) Uani 1 1 d . . . . .
C4 C 0.7469(4) 0.2650(3) 0.07549(10) 0.0705(7) Uani 1 1 d . . . . .
C5 C 0.5454(4) 0.3890(3) 0.09576(10) 0.0682(8) Uani 1 1 d . . . . .
C6 C 0.4805(3) 0.2738(3) 0.08972(10) 0.0665(7) Uani 1 1 d . . . . .
C7 C 0.3260(4) 0.2589(4) 0.09528(12) 0.0861(9) Uani 1 1 d . . . . .
H7 H 0.2817 0.1816 0.0910 0.103 Uiso 1 1 calc R U . . .
C8 C 0.2377(4) 0.3601(5) 0.10733(13) 0.1001(12) Uani 1 1 d . . . . .
H8 H 0.1332 0.3510 0.1117 0.120 Uiso 1 1 calc R U . . .
C9 C 0.3035(5) 0.4738(4) 0.11282(13) 0.0969(12) Uani 1 1 d . . . . .
H9 H 0.2419 0.5411 0.1207 0.116 Uiso 1 1 calc R U . . .
C10 C 0.4593(4) 0.4922(3) 0.10708(12) 0.0836(9) Uani 1 1 d . . . . .
H10 H 0.5031 0.5699 0.1107 0.100 Uiso 1 1 calc R U . . .
C11 C 0.8089(4) 0.4838(3) 0.09329(13) 0.0848(10) Uani 1 1 d . . . . .
H11A H 0.7667 0.5558 0.0762 0.102 Uiso 1 1 calc R U . . .
H11B H 0.9036 0.4631 0.0762 0.102 Uiso 1 1 calc R U . . .
C12 C 0.8429(3) 0.5166(3) 0.14792(13) 0.0752(8) Uani 1 1 d . . . . .
C13 C 0.8448(4) 0.4301(3) 0.18673(14) 0.0913(10) Uani 1 1 d . . . . .
H13 H 0.8195 0.3485 0.1796 0.110 Uiso 1 1 calc R U . . .
C14 C 0.8841(5) 0.4637(5) 0.23605(17) 0.1183(14) Uani 1 1 d . . . . .
H14 H 0.8862 0.4044 0.2619 0.142 Uiso 1 1 calc R U . . .
C15 C 0.9202(5) 0.5839(7) 0.2472(2) 0.1336(17) Uani 1 1 d . . . . .
H15 H 0.9468 0.6072 0.2804 0.160 Uiso 1 1 calc R U . . .
C16 C 0.9160(6) 0.6686(5) 0.2084(3) 0.1443(19) Uani 1 1 d . . . . .
H16 H 0.9391 0.7506 0.2156 0.173 Uiso 1 1 calc R U . . .
C17 C 0.8793(4) 0.6362(3) 0.15999(19) 0.1081(12) Uani 1 1 d . . . . .
H17 H 0.8787 0.6960 0.1343 0.130 Uiso 1 1 calc R U . . .
C18 C 0.6202(4) -0.1289(3) 0.05550(11) 0.0721(8) Uani 1 1 d . . . . .
H18 H 0.6439 -0.1794 0.0833 0.087 Uiso 1 1 calc R U . . .
C19 C 0.5955(4) -0.1829(3) 0.00493(12) 0.0795(9) Uani 1 1 d . . . . .
C20A C 0.594(4) -0.3584(18) -0.0461(7) 0.229(15) Uani 0.510(14) 1 d . . P A 1
H20A H 0.5216 -0.4242 -0.0395 0.274 Uiso 0.510(14) 1 calc R U P A 1
H20B H 0.5404 -0.2971 -0.0664 0.274 Uiso 0.510(14) 1 calc R U P A 1
C21A C 0.6774(14) -0.3960(18) -0.0702(6) 0.167(9) Uani 0.510(14) 1 d . . P A 1
H21A H 0.6302 -0.4285 -0.1006 0.251 Uiso 0.510(14) 1 calc R U P A 1
H21B H 0.7488 -0.3327 -0.0796 0.251 Uiso 0.510(14) 1 calc R U P A 1
H21C H 0.7298 -0.4611 -0.0525 0.251 Uiso 0.510(14) 1 calc R U P A 1
O4A O 0.626(2) -0.297(2) 0.0065(7) 0.130(7) Uani 0.510(14) 1 d . . P A 1
C20B C 0.5547(15) -0.3846(16) -0.0371(6) 0.095(4) Uani 0.490(14) 1 d . . P A 2
H20C H 0.4453 -0.3791 -0.0415 0.114 Uiso 0.490(14) 1 calc R U P A 2
H20D H 0.6009 -0.3457 -0.0669 0.114 Uiso 0.490(14) 1 calc R U P A 2
C21B C 0.588(2) -0.4882(11) -0.0378(5) 0.140(6) Uani 0.490(14) 1 d . . P A 2
H21D H 0.5540 -0.5244 -0.0695 0.210 Uiso 0.490(14) 1 calc R U P A 2
H21E H 0.6961 -0.4962 -0.0350 0.210 Uiso 0.490(14) 1 calc R U P A 2
H21F H 0.5398 -0.5298 -0.0095 0.210 Uiso 0.490(14) 1 calc R U P A 2
O4B O 0.594(2) -0.3141(19) 0.0063(8) 0.089(4) Uani 0.490(14) 1 d . . P A 2
C22 C 0.5834(4) -0.0012(3) 0.20454(10) 0.0801(9) Uani 1 1 d . . . . .
C23 C 0.5008(5) -0.1140(3) 0.18515(14) 0.1045(12) Uani 1 1 d . . . . .
H23A H 0.5718 -0.1807 0.1811 0.157 Uiso 1 1 calc R U . . .
H23B H 0.4235 -0.1374 0.2094 0.157 Uiso 1 1 calc R U . . .
H23C H 0.4543 -0.0958 0.1526 0.157 Uiso 1 1 calc R U . . .
C24 C 0.6719(5) -0.0310(5) 0.25361(13) 0.1342(17) Uani 1 1 d . . . . .
H24A H 0.7237 0.0419 0.2653 0.201 Uiso 1 1 calc R U . . .
H24B H 0.6025 -0.0588 0.2797 0.201 Uiso 1 1 calc R U . . .
H24C H 0.7451 -0.0946 0.2466 0.201 Uiso 1 1 calc R U . . .
C25 C 0.4791(5) 0.1094(4) 0.21212(15) 0.1145(13) Uani 1 1 d . . . . .
H25A H 0.5375 0.1782 0.2244 0.172 Uiso 1 1 calc R U . . .
H25B H 0.4324 0.1306 0.1800 0.172 Uiso 1 1 calc R U . . .
H25C H 0.4017 0.0891 0.2367 0.172 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.467(2) . ?
S1 N1 1.718(2) . ?
S1 C22 1.838(3) . ?
N1 C1 1.403(4) . ?
N1 C3 1.506(3) . ?
N2 C4 1.358(3) . ?
N2 C5 1.414(4) . ?
N2 C11 1.443(4) . ?
O2 C4 1.216(4) . ?
O3 C19 1.197(3) . ?
C1 C18 1.320(4) . ?
C1 C2 1.506(4) . ?
C2 C3 1.556(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C6 1.487(4) . ?
C3 C4 1.527(4) . ?
C5 C6 1.380(4) . ?
C5 C10 1.382(4) . ?
C6 C7 1.374(4) . ?
C7 C8 1.379(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.368(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.391(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.496(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C17 1.370(4) . ?
C12 C13 1.378(4) . ?
C13 C14 1.378(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.365(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.348(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.456(4) . ?
C18 H18 0.9300 . ?
C19 O4A 1.27(2) . ?
C19 O4B 1.42(2) . ?
C20A C21A 1.05(3) . ?
C20A O4A 1.55(2) . ?
C20A H20A 0.9700 . ?
C20A H20B 0.9700 . ?
C21A H21A 0.9600 . ?
C21A H21B 0.9600 . ?
C21A H21C 0.9600 . ?
C20B C21B 1.158(15) . ?
C20B O4B 1.41(2) . ?
C20B H20C 0.9700 . ?
C20B H20D 0.9700 . ?
C21B H21D 0.9600 . ?
C21B H21E 0.9600 . ?
C21B H21F 0.9600 . ?
C22 C23 1.508(5) . ?
C22 C25 1.520(5) . ?
C22 C24 1.529(5) . ?
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 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
O1 S1 N1 108.00(11) . . ?
O1 S1 C22 107.62(14) . . ?
N1 S1 C22 98.82(13) . . ?
C1 N1 C3 94.13(19) . . ?
C1 N1 S1 127.3(2) . . ?
C3 N1 S1 124.06(17) . . ?
C4 N2 C5 110.9(3) . . ?
C4 N2 C11 124.1(3) . . ?
C5 N2 C11 124.9(3) . . ?
C18 C1 N1 132.9(3) . . ?
C18 C1 C2 135.5(3) . . ?
N1 C1 C2 91.5(2) . . ?
C1 C2 C3 88.18(19) . . ?
C1 C2 H2A 114.0 . . ?
C3 C2 H2A 114.0 . . ?
C1 C2 H2B 114.0 . . ?
C3 C2 H2B 114.0 . . ?
H2A C2 H2B 111.2 . . ?
C6 C3 N1 117.3(2) . . ?
C6 C3 C4 103.7(2) . . ?
N1 C3 C4 114.4(2) . . ?
C6 C3 C2 120.2(2) . . ?
N1 C3 C2 85.85(19) . . ?
C4 C3 C2 115.5(2) . . ?
O2 C4 N2 126.2(3) . . ?
O2 C4 C3 126.5(3) . . ?
N2 C4 C3 107.3(3) . . ?
C6 C5 C10 122.0(3) . . ?
C6 C5 N2 110.0(3) . . ?
C10 C5 N2 128.0(3) . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 C3 131.8(3) . . ?
C5 C6 C3 108.0(3) . . ?
C6 C7 C8 119.1(4) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C9 C8 C7 120.1(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 122.3(4) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C5 C10 C9 116.4(4) . . ?
C5 C10 H10 121.8 . . ?
C9 C10 H10 121.8 . . ?
N2 C11 C12 114.1(3) . . ?
N2 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
N2 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C17 C12 C13 118.1(4) . . ?
C17 C12 C11 119.3(3) . . ?
C13 C12 C11 122.6(3) . . ?
C12 C13 C14 120.5(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 118.3(5) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C17 C16 C15 121.6(5) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C12 121.1(5) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
C1 C18 C19 120.0(3) . . ?
C1 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
O3 C19 O4A 124.6(9) . . ?
O3 C19 O4B 121.5(8) . . ?
O3 C19 C18 125.8(3) . . ?
O4A C19 C18 109.3(8) . . ?
O4B C19 C18 112.3(8) . . ?
C21A C20A O4A 125(3) . . ?
C21A C20A H20A 106.2 . . ?
O4A C20A H20A 106.2 . . ?
C21A C20A H20B 106.2 . . ?
O4A C20A H20B 106.2 . . ?
H20A C20A H20B 106.4 . . ?
C20A C21A H21A 109.5 . . ?
C20A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C20A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C19 O4A C20A 110.5(15) . . ?
C21B C20B O4B 118.5(12) . . ?
C21B C20B H20C 107.7 . . ?
O4B C20B H20C 107.7 . . ?
C21B C20B H20D 107.7 . . ?
O4B C20B H20D 107.7 . . ?
H20C C20B H20D 107.1 . . ?
C20B C21B H21D 109.5 . . ?
C20B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C20B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C19 O4B C20B 121.6(15) . . ?
C23 C22 C25 113.0(3) . . ?
C23 C22 C24 110.7(3) . . ?
C25 C22 C24 111.3(3) . . ?
C23 C22 S1 111.1(2) . . ?
C25 C22 S1 105.5(2) . . ?
C24 C22 S1 104.7(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 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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 S1 N1 C1 4.9(3) . . . . ?
C22 S1 N1 C1 -106.9(2) . . . . ?
O1 S1 N1 C3 -123.7(2) . . . . ?
C22 S1 N1 C3 124.5(2) . . . . ?
C3 N1 C1 C18 176.2(4) . . . . ?
S1 N1 C1 C18 36.7(5) . . . . ?
C3 N1 C1 C2 -4.4(2) . . . . ?
S1 N1 C1 C2 -143.9(2) . . . . ?
C18 C1 C2 C3 -176.4(4) . . . . ?
N1 C1 C2 C3 4.2(2) . . . . ?
C1 N1 C3 C6 126.2(3) . . . . ?
S1 N1 C3 C6 -92.4(3) . . . . ?
C1 N1 C3 C4 -112.0(2) . . . . ?
S1 N1 C3 C4 29.5(3) . . . . ?
C1 N1 C3 C2 4.2(2) . . . . ?
S1 N1 C3 C2 145.7(2) . . . . ?
C1 C2 C3 C6 -123.2(3) . . . . ?
C1 C2 C3 N1 -3.9(2) . . . . ?
C1 C2 C3 C4 111.2(3) . . . . ?
C5 N2 C4 O2 -179.0(3) . . . . ?
C11 N2 C4 O2 -1.9(5) . . . . ?
C5 N2 C4 C3 0.8(3) . . . . ?
C11 N2 C4 C3 177.9(2) . . . . ?
C6 C3 C4 O2 178.1(3) . . . . ?
N1 C3 C4 O2 49.1(4) . . . . ?
C2 C3 C4 O2 -48.3(4) . . . . ?
C6 C3 C4 N2 -1.8(3) . . . . ?
N1 C3 C4 N2 -130.7(2) . . . . ?
C2 C3 C4 N2 131.9(2) . . . . ?
C4 N2 C5 C6 0.6(3) . . . . ?
C11 N2 C5 C6 -176.5(3) . . . . ?
C4 N2 C5 C10 -177.9(3) . . . . ?
C11 N2 C5 C10 5.0(5) . . . . ?
C10 C5 C6 C7 -0.4(4) . . . . ?
N2 C5 C6 C7 -179.0(2) . . . . ?
C10 C5 C6 C3 176.8(3) . . . . ?
N2 C5 C6 C3 -1.7(3) . . . . ?
N1 C3 C6 C7 -53.8(4) . . . . ?
C4 C3 C6 C7 179.0(3) . . . . ?
C2 C3 C6 C7 48.0(4) . . . . ?
N1 C3 C6 C5 129.3(2) . . . . ?
C4 C3 C6 C5 2.1(3) . . . . ?
C2 C3 C6 C5 -128.8(3) . . . . ?
C5 C6 C7 C8 -0.5(5) . . . . ?
C3 C6 C7 C8 -177.1(3) . . . . ?
C6 C7 C8 C9 1.0(5) . . . . ?
C7 C8 C9 C10 -0.6(5) . . . . ?
C6 C5 C10 C9 0.9(4) . . . . ?
N2 C5 C10 C9 179.2(3) . . . . ?
C8 C9 C10 C5 -0.4(5) . . . . ?
C4 N2 C11 C12 -101.8(3) . . . . ?
C5 N2 C11 C12 74.9(4) . . . . ?
N2 C11 C12 C17 -150.7(3) . . . . ?
N2 C11 C12 C13 31.8(4) . . . . ?
C17 C12 C13 C14 -0.7(5) . . . . ?
C11 C12 C13 C14 176.8(3) . . . . ?
C12 C13 C14 C15 0.7(6) . . . . ?
C13 C14 C15 C16 0.0(7) . . . . ?
C14 C15 C16 C17 -0.7(8) . . . . ?
C15 C16 C17 C12 0.7(8) . . . . ?
C13 C12 C17 C16 0.0(6) . . . . ?
C11 C12 C17 C16 -177.6(4) . . . . ?
N1 C1 C18 C19 174.6(3) . . . . ?
C2 C1 C18 C19 -4.5(6) . . . . ?
C1 C18 C19 O3 -0.6(6) . . . . ?
C1 C18 C19 O4A 173.7(12) . . . . ?
C1 C18 C19 O4B -172.9(9) . . . . ?
O3 C19 O4A C20A -8(2) . . . . ?
O4B C19 O4A C20A 72(7) . . . . ?
C18 C19 O4A C20A 177.4(16) . . . . ?
C21A C20A O4A C19 114(3) . . . . ?
O3 C19 O4B C20B 0(2) . . . . ?
O4A C19 O4B C20B -108(8) . . . . ?
C18 C19 O4B C20B 172.7(13) . . . . ?
C21B C20B O4B C19 162.9(17) . . . . ?
O1 S1 C22 C23 -56.0(3) . . . . ?
N1 S1 C22 C23 56.2(3) . . . . ?
O1 S1 C22 C25 -178.9(2) . . . . ?
N1 S1 C22 C25 -66.7(2) . . . . ?
O1 S1 C22 C24 63.6(3) . . . . ?
N1 S1 C22 C24 175.7(3) . . . . ?

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.027

_shelxl_version_number           2014/4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'Isopropyl ether'
