# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_17mg016_0m
_database_code_depnum_ccdc_archive 'CCDC 1919153'
loop_
_audit_author_name
_audit_author_address
'Michael Gardiner'
;Australian National University
Australia
;
_audit_update_record             
;
2019-05-28 deposited with the CCDC.	2019-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 N2 O6 S'
_chemical_formula_weight         352.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   6.7486(2)
_cell_length_b                   10.2915(3)
_cell_length_c                   11.4126(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.952(2)
_cell_angle_gamma                90
_cell_volume                     789.68(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    9886
_cell_measurement_theta_min      3.89
_cell_measurement_theta_max      66.69

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.633
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.072
_exptl_absorpt_coefficient_mu    2.153
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6751
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0749 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.9145.
The λ/2 correction factor is Not present.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13713
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.888
_diffrn_reflns_theta_max         66.682
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             2764
_reflns_number_gt                2678
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.875
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.962

_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_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?

_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)+(0.0432P)²+0.2043P] 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 1224 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2764
_refine_ls_number_parameters     227
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0703
_refine_ls_wR_factor_gt          0.0694
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.24441(9) 0.40242(6) 0.79719(5) 0.01590(17) Uani 1 1 d . . . . .
O1 O 0.2089(3) 0.4923(2) 0.88827(16) 0.0237(5) Uani 1 1 d . . . . .
O2 O 0.0959(3) 0.31325(19) 0.75245(17) 0.0222(4) Uani 1 1 d . . . . .
O3 O 1.1196(3) 0.1627(2) 0.99809(18) 0.0276(5) Uani 1 1 d . . . . .
O4 O 1.0289(3) 0.0159(2) 0.86872(18) 0.0280(5) Uani 1 1 d . . . . .
O5 O 0.3010(3) 0.3339(2) 0.54263(17) 0.0237(5) Uani 1 1 d . . . . .
O6 O 0.3529(3) 0.5436(2) 0.50081(17) 0.0254(5) Uani 1 1 d . . . . .
N1 N 0.9990(3) 0.1152(2) 0.9236(2) 0.0200(5) Uani 1 1 d . . . . .
N2 N 0.3027(3) 0.4945(2) 0.68534(18) 0.0154(5) Uani 1 1 d . . . . .
C1 C 0.4637(4) 0.3141(3) 0.8398(2) 0.0164(5) Uani 1 1 d . . . . .
C2 C 0.5918(4) 0.3575(3) 0.9336(2) 0.0187(6) Uani 1 1 d . . . . .
H2 H 0.5605 0.4306 0.9761 0.022 Uiso 1 1 calc R U . . .
C3 C 0.7667(4) 0.2902(3) 0.9626(2) 0.0194(6) Uani 1 1 d . . . . .
H3 H 0.8545 0.3170 1.0252 0.023 Uiso 1 1 calc R U . . .
C4 C 0.8079(4) 0.1829(3) 0.8968(2) 0.0160(5) Uani 1 1 d . . . . .
C5 C 0.6814(4) 0.1375(3) 0.8042(2) 0.0214(6) Uani 1 1 d . . . . .
H5 H 0.7137 0.0642 0.7622 0.026 Uiso 1 1 calc R U . . .
C6 C 0.5051(4) 0.2039(3) 0.7755(3) 0.0218(6) Uani 1 1 d . . . . .
H6 H 0.4160 0.1753 0.7142 0.026 Uiso 1 1 calc R U . . .
C7 C 0.3161(4) 0.4450(3) 0.5731(3) 0.0191(6) Uani 1 1 d . . . . .
C8 C 0.5962(5) 0.8037(3) 0.7751(3) 0.0314(7) Uani 1 1 d . . . . .
H8A H 0.6197 0.8365 0.6988 0.047 Uiso 1 1 calc R U . . .
H8B H 0.7106 0.8201 0.8291 0.047 Uiso 1 1 calc R U . . .
H8C H 0.4824 0.8464 0.8025 0.047 Uiso 1 1 calc R U . . .
C9 C 0.7340(4) 0.5874(3) 0.7188(3) 0.0271(7) Uani 1 1 d . . . . .
H9A H 0.7626 0.6269 0.6459 0.041 Uiso 1 1 calc R U . . .
H9B H 0.7012 0.4975 0.7056 0.041 Uiso 1 1 calc R U . . .
H9C H 0.8486 0.5940 0.7745 0.041 Uiso 1 1 calc R U . . .
C10 C 0.5579(4) 0.6573(3) 0.7672(3) 0.0216(6) Uani 1 1 d . . . . .
H10 H 0.5457 0.6251 0.8470 0.026 Uiso 1 1 calc R U . . .
C11 C 0.3595(4) 0.6333(3) 0.6950(2) 0.0191(6) Uani 1 1 d . . . . .
H11 H 0.2541 0.6824 0.7291 0.023 Uiso 1 1 calc R U . . .
C12 C 0.3609(5) 0.6674(3) 0.5629(3) 0.0259(7) Uani 1 1 d . . . . .
H12 H 0.4870 0.7103 0.5505 0.031 Uiso 1 1 calc R U . . .
C13 C 0.1926(5) 0.7522(3) 0.5132(3) 0.0391(9) Uani 1 1 d . . . . .
H13 H 0.1077 0.7204 0.4513 0.047 Uiso 1 1 calc R U . . .
C14 C 0.1605(5) 0.8671(3) 0.5527(3) 0.0287(8) Uani 1 1 d . . . . .
C15 C 0.1374(7) 0.9861(5) 0.5916(4) 0.0530(12) Uani 1 1 d . . . . .
H15A H 0.049(6) 0.954(4) 0.643(3) 0.032(10) Uiso 1 1 d . . . . .
H15B H 0.193(14) 1.071(9) 0.563(8) 0.19(4) 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
S1 O2 1.421(2) . ?
S1 O1 1.427(2) . ?
S1 N2 1.664(2) . ?
S1 C1 1.769(3) . ?
O3 N1 1.226(3) . ?
O4 N1 1.225(3) . ?
O5 C7 1.198(4) . ?
O6 C7 1.344(4) . ?
O6 C12 1.456(4) . ?
N1 C4 1.474(3) . ?
N2 C7 1.389(4) . ?
N2 C11 1.481(4) . ?
C1 C2 1.390(4) . ?
C1 C6 1.392(4) . ?
C2 C3 1.383(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(4) . ?
C5 C6 1.387(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C10 1.530(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.533(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.530(4) . ?
C10 H10 0.9800 . ?
C11 C12 1.550(4) . ?
C11 H11 0.9800 . ?
C12 C13 1.504(4) . ?
C12 H12 0.9800 . ?
C13 C14 1.291(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.316(6) . ?
C15 H15A 0.93(4) . ?
C15 H15B 1.01(10) . ?

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 S1 O1 121.53(13) . . ?
O2 S1 N2 107.35(11) . . ?
O1 S1 N2 104.78(12) . . ?
O2 S1 C1 108.31(13) . . ?
O1 S1 C1 108.76(12) . . ?
N2 S1 C1 104.86(12) . . ?
C7 O6 C12 111.3(2) . . ?
O4 N1 O3 123.9(2) . . ?
O4 N1 C4 117.9(2) . . ?
O3 N1 C4 118.2(2) . . ?
C7 N2 C11 112.7(2) . . ?
C7 N2 S1 122.50(19) . . ?
C11 N2 S1 124.68(18) . . ?
C2 C1 C6 121.9(3) . . ?
C2 C1 S1 119.8(2) . . ?
C6 C1 S1 118.3(2) . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 118.6(2) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 123.2(3) . . ?
C3 C4 N1 118.7(2) . . ?
C5 C4 N1 118.1(2) . . ?
C4 C5 C6 118.4(3) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
O5 C7 O6 123.9(3) . . ?
O5 C7 N2 127.4(3) . . ?
O6 C7 N2 108.7(2) . . ?
C10 C8 H8A 109.5 . . ?
C10 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C10 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
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 . . ?
C11 C10 C8 109.1(2) . . ?
C11 C10 C9 113.6(2) . . ?
C8 C10 C9 110.5(3) . . ?
C11 C10 H10 107.8 . . ?
C8 C10 H10 107.8 . . ?
C9 C10 H10 107.8 . . ?
N2 C11 C10 113.9(2) . . ?
N2 C11 C12 99.7(2) . . ?
C10 C11 C12 114.1(2) . . ?
N2 C11 H11 109.6 . . ?
C10 C11 H11 109.6 . . ?
C12 C11 H11 109.6 . . ?
O6 C12 C13 109.2(2) . . ?
O6 C12 C11 105.8(2) . . ?
C13 C12 C11 115.4(3) . . ?
O6 C12 H12 108.7 . . ?
C13 C12 H12 108.7 . . ?
C11 C12 H12 108.7 . . ?
C14 C13 C12 123.0(3) . . ?
C14 C13 H13 118.5 . . ?
C12 C13 H13 118.5 . . ?
C13 C14 C15 176.9(4) . . ?
C14 C15 H15A 89(2) . . ?
C14 C15 H15B 129(6) . . ?
H15A C15 H15B 142(6) . . ?

_refine_diff_density_max         0.179
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.053

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_17mg018_0m
_database_code_depnum_ccdc_archive 'CCDC 1919154'
loop_
_audit_author_name
_audit_author_address
'Michael Gardiner'
;Australian National University
Australia
;
_audit_update_record             
;
2019-05-28 deposited with the CCDC.	2019-08-16 downloaded from the CCDC.
;
_audit_creation_date             2019-05-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H24 N2 O7 S'
_chemical_formula_sum            'C22 H24 N2 O7 S'
_chemical_formula_weight         460.49
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_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'
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                   7.5533(2)
_cell_length_b                   9.7486(2)
_cell_length_c                   29.0797(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2141.26(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8999
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      66.59
_cell_measurement_theta_min      4.78
_shelx_estimated_absorpt_T_max   0.917
_shelx_estimated_absorpt_T_min   0.778
_exptl_absorpt_coefficient_mu    1.763
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0736 before and 0.0488 after correction.
The Ratio of minimum to maximum transmission is 0.9145.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            12058
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.586
_diffrn_reflns_theta_min         3.039
_diffrn_ambient_temperature      125.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3662
_reflns_number_total             3772
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 1508 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3772
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+0.8703P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0931
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C17(H17), C18(H18), C21(H21),
 C22(H22)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.66917(10) 0.64259(9) 0.19394(2) 0.0305(2) Uani 1 1 d . . . . .
O1 O 0.7155(4) 0.7767(3) 0.20933(9) 0.0477(7) Uani 1 1 d . . . . .
O2 O 0.7619(3) 0.5259(3) 0.20993(8) 0.0429(6) Uani 1 1 d . . . . .
O3 O 0.8297(4) 0.7251(3) -0.02762(9) 0.0480(7) Uani 1 1 d . . . . .
O4 O 0.6571(4) 0.5484(3) -0.03167(8) 0.0434(6) Uani 1 1 d . . . . .
O5 O 0.4221(3) 0.3908(2) 0.19011(8) 0.0328(5) Uani 1 1 d . . . . .
O6 O 0.2088(3) 0.5143(2) 0.22452(7) 0.0263(5) Uani 1 1 d . . . . .
O7 O 0.4679(3) 0.5798(3) 0.50722(7) 0.0354(6) Uani 1 1 d . . . . .
N1 N 0.4593(3) 0.6235(3) 0.20757(9) 0.0273(6) Uani 1 1 d . . . . .
N2 N 0.7361(4) 0.6369(3) -0.01014(9) 0.0328(6) Uani 1 1 d . . . . .
C1 C 0.6802(4) 0.6420(3) 0.13285(10) 0.0246(6) Uani 1 1 d . . . . .
C2 C 0.6548(4) 0.5194(3) 0.10992(10) 0.0268(6) Uani 1 1 d . . . . .
H2 H 0.6264 0.4381 0.1264 0.032 Uiso 1 1 calc R . . . .
C3 C 0.6714(5) 0.5173(3) 0.06221(11) 0.0287(6) Uani 1 1 d . . . . .
H3 H 0.6520 0.4354 0.0453 0.034 Uiso 1 1 calc R . . . .
C4 C 0.7170(4) 0.6378(3) 0.04029(10) 0.0257(6) Uani 1 1 d . . . . .
C5 C 0.7454(5) 0.7594(3) 0.06321(12) 0.0315(7) Uani 1 1 d . . . . .
H5 H 0.7791 0.8397 0.0469 0.038 Uiso 1 1 calc R . . . .
C6 C 0.7237(4) 0.7621(3) 0.11063(12) 0.0305(7) Uani 1 1 d . . . . .
H6 H 0.7386 0.8450 0.1274 0.037 Uiso 1 1 calc R . . . .
C7 C 0.3693(4) 0.4958(3) 0.20590(10) 0.0253(6) Uani 1 1 d . . . . .
C8 C 0.1509(6) 0.9224(4) 0.18394(14) 0.0472(9) Uani 1 1 d . . . . .
H8A H 0.1108 0.9636 0.1550 0.071 Uiso 1 1 calc GR . . . .
H8B H 0.2148 0.9912 0.2021 0.071 Uiso 1 1 calc GR . . . .
H8C H 0.0484 0.8897 0.2014 0.071 Uiso 1 1 calc GR . . . .
C9 C 0.2716(5) 0.8042(4) 0.17375(12) 0.0376(8) Uani 1 1 d . . . . .
H9 H 0.3785 0.8423 0.1580 0.045 Uiso 1 1 calc R . . . .
C10 C 0.1829(6) 0.7041(4) 0.14011(11) 0.0392(8) Uani 1 1 d . . . . .
H10A H 0.1527 0.7525 0.1116 0.059 Uiso 1 1 calc GR . . . .
H10B H 0.0749 0.6671 0.1541 0.059 Uiso 1 1 calc GR . . . .
H10C H 0.2645 0.6287 0.1332 0.059 Uiso 1 1 calc GR . . . .
C11 C 0.3351(4) 0.7353(3) 0.21822(10) 0.0267(6) Uani 1 1 d . . . . .
H11 H 0.3933 0.8043 0.2387 0.032 Uiso 1 1 calc R . . . .
C12 C 0.1985(4) 0.6509(3) 0.24571(9) 0.0239(6) Uani 1 1 d . . . . .
H12 H 0.0770 0.6905 0.2424 0.029 Uiso 1 1 calc R . . . .
C13 C 0.2476(4) 0.6354(3) 0.29544(10) 0.0241(6) Uani 1 1 d . . . . .
H13 H 0.3506 0.5826 0.3016 0.029 Uiso 1 1 calc R . . . .
C14 C 0.1652(4) 0.6862(3) 0.33192(10) 0.0230(6) Uani 1 1 d . . . . .
C15 C -0.0031(4) 0.7677(3) 0.32928(11) 0.0306(7) Uani 1 1 d . . . . .
H15A H -0.0451 0.7697 0.2974 0.046 Uiso 1 1 calc GR . . . .
H15B H 0.0191 0.8616 0.3399 0.046 Uiso 1 1 calc GR . . . .
H15C H -0.0932 0.7250 0.3489 0.046 Uiso 1 1 calc GR . . . .
C16 C 0.2425(4) 0.6628(3) 0.37876(10) 0.0235(6) Uani 1 1 d . . . . .
C17 C 0.1352(4) 0.6506(3) 0.41750(10) 0.0262(6) Uani 1 1 d . . . . .
H17 H 0.0107 0.6604 0.4142 0.031 Uiso 1 1 calc R . . . .
C18 C 0.2050(5) 0.6245(3) 0.46103(10) 0.0282(7) Uani 1 1 d . . . . .
H18 H 0.1287 0.6169 0.4869 0.034 Uiso 1 1 calc R . . . .
C19 C 0.3856(5) 0.6097(3) 0.46640(10) 0.0265(7) Uani 1 1 d . . . . .
C20 C 0.3583(6) 0.5587(4) 0.54654(11) 0.0383(8) Uani 1 1 d . . . . .
H20A H 0.2886 0.6417 0.5524 0.057 Uiso 1 1 calc GR . . . .
H20B H 0.4327 0.5388 0.5733 0.057 Uiso 1 1 calc GR . . . .
H20C H 0.2784 0.4813 0.5409 0.057 Uiso 1 1 calc GR . . . .
C21 C 0.4962(5) 0.6242(4) 0.42834(11) 0.0319(7) Uani 1 1 d . . . . .
H21 H 0.6208 0.6164 0.4319 0.038 Uiso 1 1 calc R . . . .
C22 C 0.4251(4) 0.6499(3) 0.38536(10) 0.0274(6) Uani 1 1 d . . . . .
H22 H 0.5022 0.6589 0.3597 0.033 Uiso 1 1 calc R . . . .


_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 1.426(3) . ?
S1 O2 1.414(3) . ?
S1 N1 1.645(3) . ?
S1 C1 1.778(3) . ?
O3 N2 1.224(4) . ?
O4 N2 1.222(4) . ?
O5 C7 1.191(4) . ?
O6 C7 1.340(4) . ?
O6 C12 1.469(4) . ?
O7 C19 1.371(4) . ?
O7 C20 1.426(4) . ?
N1 C7 1.419(4) . ?
N1 C11 1.471(4) . ?
N2 C4 1.474(4) . ?
C1 C2 1.383(4) . ?
C1 C6 1.377(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(5) . ?
C4 C5 1.376(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(5) . ?
C6 H6 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 C9 1.499(5) . ?
C9 H9 1.0000 . ?
C9 C10 1.536(5) . ?
C9 C11 1.535(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 1.0000 . ?
C11 C12 1.543(4) . ?
C12 H12 1.0000 . ?
C12 C13 1.501(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.326(4) . ?
C14 C15 1.501(4) . ?
C14 C16 1.499(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.393(4) . ?
C16 C22 1.398(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.395(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.380(5) . ?
C19 C21 1.394(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C22 1.383(4) . ?
C22 H22 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 105.36(15) . . ?
O1 S1 C1 107.74(16) . . ?
O2 S1 O1 120.87(17) . . ?
O2 S1 N1 107.86(15) . . ?
O2 S1 C1 107.62(15) . . ?
N1 S1 C1 106.61(14) . . ?
C7 O6 C12 109.8(2) . . ?
C19 O7 C20 117.5(3) . . ?
C7 N1 S1 123.6(2) . . ?
C7 N1 C11 110.6(2) . . ?
C11 N1 S1 125.5(2) . . ?
O3 N2 C4 117.8(3) . . ?
O4 N2 O3 124.4(3) . . ?
O4 N2 C4 117.8(3) . . ?
C2 C1 S1 118.5(2) . . ?
C6 C1 S1 118.5(2) . . ?
C6 C1 C2 122.8(3) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.7(3) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.0(3) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 N2 118.6(3) . . ?
C5 C4 N2 118.2(3) . . ?
C5 C4 C3 123.2(3) . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.6(3) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 118.5(3) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
O5 C7 O6 125.1(3) . . ?
O5 C7 N1 127.3(3) . . ?
O6 C7 N1 107.6(3) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
C8 C9 H9 107.2 . . ?
C8 C9 C10 110.4(3) . . ?
C8 C9 C11 111.1(3) . . ?
C10 C9 H9 107.2 . . ?
C11 C9 H9 107.2 . . ?
C11 C9 C10 113.3(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C9 110.3(3) . . ?
N1 C11 H11 110.1 . . ?
N1 C11 C12 98.1(2) . . ?
C9 C11 H11 110.1 . . ?
C9 C11 C12 117.4(3) . . ?
C12 C11 H11 110.1 . . ?
O6 C12 C11 103.3(2) . . ?
O6 C12 H12 111.0 . . ?
O6 C12 C13 107.4(2) . . ?
C11 C12 H12 111.0 . . ?
C13 C12 C11 112.8(2) . . ?
C13 C12 H12 111.0 . . ?
C12 C13 H13 115.9 . . ?
C14 C13 C12 128.1(3) . . ?
C14 C13 H13 115.9 . . ?
C13 C14 C15 123.7(3) . . ?
C13 C14 C16 119.2(3) . . ?
C16 C14 C15 117.2(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C14 121.4(3) . . ?
C17 C16 C22 117.1(3) . . ?
C22 C16 C14 121.5(3) . . ?
C16 C17 H17 119.0 . . ?
C16 C17 C18 122.0(3) . . ?
C18 C17 H17 119.0 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18 120.1 . . ?
O7 C19 C18 124.6(3) . . ?
O7 C19 C21 115.9(3) . . ?
C18 C19 C21 119.5(3) . . ?
O7 C20 H20A 109.5 . . ?
O7 C20 H20B 109.5 . . ?
O7 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21 119.9 . . ?
C22 C21 C19 120.2(3) . . ?
C22 C21 H21 119.9 . . ?
C16 C22 H22 119.2 . . ?
C21 C22 C16 121.5(3) . . ?
C21 C22 H22 119.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
