# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_FO7223_2
_database_code_depnum_ccdc_archive 'CCDC 2141656'
loop_
_audit_author_name
_audit_author_address
'Helmar Goerls'
;University Jena
Germany
;
_audit_update_record             
;
2022-01-12 deposited with the CCDC.	2022-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 N O4 S'
_chemical_formula_sum            'C12 H11 N O4 S'
_chemical_formula_weight         265.28

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   5.8270(2)
_cell_length_b                   10.1224(3)
_cell_length_c                   11.5866(3)
_cell_angle_alpha                109.654(1)
_cell_angle_beta                 99.346(2)
_cell_angle_gamma                97.107(2)
_cell_volume                     623.25(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    233(2)
_cell_measurement_reflns_used    7554
_cell_measurement_theta_min      1.912
_cell_measurement_theta_max      27.483

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.112
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.088
_exptl_absorpt_coefficient_mu    0.265
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7027
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_diffrn_ambient_temperature      233(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi + omega - scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7554
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.912
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2844
_reflns_number_gt                2292
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0173P)²+0.4437P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2844
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.0980
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.60406(9) 0.71400(6) 0.36124(5) 0.04620(17) Uani 1 1 d . . . . .
O1 O 0.2120(3) 0.82252(18) 0.35879(14) 0.0549(4) Uani 1 1 d . . . . .
O2 O 0.2908(2) 0.68817(15) 0.17395(12) 0.0401(3) Uani 1 1 d . . . . .
O3 O 0.2915(3) 0.90747(17) 0.08116(17) 0.0611(5) Uani 1 1 d . . . . .
O4 O -0.1656(3) 0.52553(16) 0.10662(14) 0.0479(4) Uani 1 1 d . . . . .
N1 N 0.0896(3) 0.72005(17) 0.11437(14) 0.0357(4) Uani 1 1 d . . . . .
C1 C 0.3369(3) 0.7540(2) 0.30388(18) 0.0362(4) Uani 1 1 d . . . . .
C2 C 0.1107(4) 0.8267(2) 0.06471(19) 0.0383(4) Uani 1 1 d . . . . .
C3 C -0.1342(4) 0.8138(2) -0.0093(2) 0.0420(5) Uani 1 1 d . . . . .
H3B H -0.121(4) 0.808(3) -0.092(2) 0.065(7) Uiso 1 1 d . . . . .
H3A H -0.192(4) 0.895(3) 0.024(2) 0.061(7) Uiso 1 1 d . . . . .
C4 C -0.2835(4) 0.6830(3) -0.0044(2) 0.0435(5) Uani 1 1 d . . . . .
H4B H -0.413(5) 0.704(3) 0.029(2) 0.058(7) Uiso 1 1 d . . . . .
H4A H -0.338(5) 0.608(3) -0.085(3) 0.071(8) Uiso 1 1 d . . . . .
C5 C -0.1267(3) 0.6273(2) 0.07694(17) 0.0352(4) Uani 1 1 d . . . . .
C6 C 0.6170(6) 0.8031(4) 0.5282(2) 0.0632(8) Uani 1 1 d . . . . .
H6B H 0.467(7) 0.766(4) 0.541(3) 0.118(14) Uiso 1 1 d . . . . .
H6A H 0.630(5) 0.900(4) 0.543(3) 0.091(11) Uiso 1 1 d . . . . .
C7 C 0.8297(4) 0.7739(2) 0.60209(18) 0.0441(5) Uani 1 1 d . . . . .
C8 C 0.8242(5) 0.6427(3) 0.6124(3) 0.0659(7) Uani 1 1 d . . . . .
H8 H 0.686(6) 0.569(3) 0.569(3) 0.097(10) Uiso 1 1 d . . . . .
C9 C 1.0128(6) 0.6124(4) 0.6796(3) 0.0785(9) Uani 1 1 d . . . . .
H9 H 1.004(6) 0.512(4) 0.686(3) 0.124(13) Uiso 1 1 d . . . . .
C10 C 1.2080(6) 0.7142(4) 0.7397(2) 0.0734(9) Uani 1 1 d . . . . .
H10 H 1.342(6) 0.693(3) 0.786(3) 0.105(11) Uiso 1 1 d . . . . .
C11 C 1.2196(5) 0.8470(4) 0.7331(2) 0.0694(9) Uani 1 1 d . . . . .
H11 H 1.340(6) 0.915(3) 0.765(3) 0.092(11) Uiso 1 1 d . . . . .
C12 C 1.0286(4) 0.8776(3) 0.6624(2) 0.0533(6) Uani 1 1 d . . . . .
H12 H 1.032(4) 0.965(3) 0.655(2) 0.053(7) 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 C1 1.741(2) . ?
S1 C6 1.824(2) . ?
O1 C1 1.181(2) . ?
O2 C1 1.390(2) . ?
O2 N1 1.3911(18) . ?
O3 C2 1.197(2) . ?
O4 C5 1.198(2) . ?
N1 C5 1.384(2) . ?
N1 C2 1.386(2) . ?
C2 C3 1.507(3) . ?
C3 C4 1.515(3) . ?
C3 H3B 0.96(3) . ?
C3 H3A 0.92(3) . ?
C4 C5 1.499(3) . ?
C4 H4B 0.92(3) . ?
C4 H4A 0.96(3) . ?
C6 C7 1.507(3) . ?
C6 H6B 0.96(4) . ?
C6 H6A 0.92(3) . ?
C7 C12 1.370(3) . ?
C7 C8 1.370(3) . ?
C8 C9 1.369(4) . ?
C8 H8 0.96(3) . ?
C9 C10 1.346(5) . ?
C9 H9 1.04(4) . ?
C10 C11 1.366(5) . ?
C10 H10 0.96(3) . ?
C11 C12 1.402(4) . ?
C11 H11 0.86(3) . ?
C12 H12 0.92(2) . ?

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
C1 S1 C6 97.83(11) . . ?
C1 O2 N1 112.66(14) . . ?
C5 N1 C2 116.98(15) . . ?
C5 N1 O2 121.06(15) . . ?
C2 N1 O2 120.25(15) . . ?
O1 C1 O2 124.02(17) . . ?
O1 C1 S1 129.66(16) . . ?
O2 C1 S1 106.32(13) . . ?
O3 C2 N1 124.23(18) . . ?
O3 C2 C3 130.77(19) . . ?
N1 C2 C3 104.99(16) . . ?
C2 C3 C4 106.03(16) . . ?
C2 C3 H3B 107.9(15) . . ?
C4 C3 H3B 114.2(15) . . ?
C2 C3 H3A 110.2(15) . . ?
C4 C3 H3A 112.3(16) . . ?
H3B C3 H3A 106(2) . . ?
C5 C4 C3 106.64(17) . . ?
C5 C4 H4B 109.6(15) . . ?
C3 C4 H4B 112.4(15) . . ?
C5 C4 H4A 107.3(16) . . ?
C3 C4 H4A 113.0(16) . . ?
H4B C4 H4A 108(2) . . ?
O4 C5 N1 124.11(18) . . ?
O4 C5 C4 130.81(19) . . ?
N1 C5 C4 105.08(16) . . ?
C7 C6 S1 108.67(17) . . ?
C7 C6 H6B 115(2) . . ?
S1 C6 H6B 105(2) . . ?
C7 C6 H6A 111.4(19) . . ?
S1 C6 H6A 106.6(19) . . ?
H6B C6 H6A 110(3) . . ?
C12 C7 C8 118.7(2) . . ?
C12 C7 C6 121.3(2) . . ?
C8 C7 C6 120.0(2) . . ?
C7 C8 C9 121.7(3) . . ?
C7 C8 H8 119.3(19) . . ?
C9 C8 H8 118.9(19) . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 H9 120(2) . . ?
C8 C9 H9 120(2) . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 H10 120(2) . . ?
C11 C10 H10 120(2) . . ?
C10 C11 C12 120.1(3) . . ?
C10 C11 H11 125(2) . . ?
C12 C11 H11 114(2) . . ?
C7 C12 C11 119.3(3) . . ?
C7 C12 H12 118.5(15) . . ?
C11 C12 H12 122.2(15) . . ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.045

