# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_dbt2_sss
_database_code_depnum_ccdc_archive 'CCDC 2361034'
loop_
_audit_author_name
_audit_author_address
'Robert Gyepes'
;Department of Inorganic Chemistry, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2024-06-06 deposited with the CCDC.	2024-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N O4'
_chemical_formula_sum            'C12 H9 N O4'
_chemical_formula_weight         231.20

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   3.8739(2)
_cell_length_b                   8.3535(4)
_cell_length_c                   31.3297(15)
_cell_angle_alpha                90
_cell_angle_beta                 92.754(2)
_cell_angle_gamma                90
_cell_volume                     1012.68(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7093
_cell_measurement_theta_min      2.8241
_cell_measurement_theta_max      72.2951

_exptl_crystal_description       needle
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.585
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.072
_exptl_absorpt_coefficient_mu    0.977
_shelx_estimated_absorpt_T_min   0.599
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Sevvana, M., Ruf, M., Usón, I., Sheldrick, G. M., and Herbst-Irmer, R. (2019)
"Non-merohedral twinning: from minerals to proteins"
Acta. Cryst. D75, 1040-1050.
doi:10.1107/S2059798319010179
;
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Kappa goniometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4831
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.824
_diffrn_reflns_theta_max         72.835
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4831
_reflns_number_gt                4398
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1429P)²+1.3402P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_number_reflns         4831
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0775
_refine_ls_wR_factor_ref         0.2185
_refine_ls_wR_factor_gt          0.2081
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6127(9) 0.7045(4) 0.56985(10) 0.0161(7) Uani 1 1 d . . . . .
C2 C 0.6198(9) 0.7250(4) 0.61465(11) 0.0165(7) Uani 1 1 d . . . . .
C3 C 0.4768(9) 0.8645(4) 0.63118(11) 0.0191(8) Uani 1 1 d . . . . .
H3 H 0.486452 0.880418 0.661238 0.023 Uiso 1 1 calc R U . . .
C4 C 0.3222(9) 0.9797(5) 0.60506(11) 0.0211(8) Uani 1 1 d . . . . .
H4 H 0.222095 1.072199 0.617033 0.025 Uiso 1 1 calc R U . . .
C5 C 0.3150(10) 0.9582(5) 0.56066(12) 0.0217(8) Uani 1 1 d . . . . .
H5 H 0.208438 1.036293 0.542333 0.026 Uiso 1 1 calc R U . . .
C6 C 0.4621(9) 0.8241(5) 0.54359(11) 0.0188(8) Uani 1 1 d . . . . .
H6 H 0.461691 0.812335 0.513433 0.023 Uiso 1 1 calc R U . . .
C7 C 0.7751(9) 0.6117(4) 0.64656(10) 0.0162(7) Uani 1 1 d . . . . .
O1 O 0.9145(7) 0.6602(3) 0.67982(8) 0.0227(6) Uani 1 1 d . . . . .
C8 C 0.7418(9) 0.4358(4) 0.63925(10) 0.0168(7) Uani 1 1 d . . . . .
C9 C 0.7756(9) 0.3619(4) 0.60173(10) 0.0178(8) Uani 1 1 d . . . . .
H9 H 0.734957 0.249733 0.601821 0.021 Uiso 1 1 calc R U . . .
C10 C 0.8671(9) 0.4300(4) 0.56020(10) 0.0185(8) Uani 1 1 d . . . . .
N1 N 0.7735(8) 0.5792(4) 0.54844(9) 0.0181(7) Uani 1 1 d . . . . .
H1N H 0.845(13) 0.606(6) 0.5232(19) 0.037(14) Uiso 1 1 d . . . . .
O2 O 1.0263(7) 0.3430(3) 0.53597(8) 0.0236(6) Uani 1 1 d . . . . .
C11 C 0.6808(9) 0.3292(5) 0.67729(10) 0.0187(8) Uani 1 1 d . . . . .
O3 O 0.7766(8) 0.1924(3) 0.67930(8) 0.0272(7) Uani 1 1 d . . . . .
O4 O 0.5063(7) 0.4053(3) 0.70628(8) 0.0243(7) Uani 1 1 d . . . . .
C12 C 0.4322(11) 0.3132(6) 0.74412(12) 0.0295(10) Uani 1 1 d . . . . .
H12A H 0.306550 0.215577 0.735603 0.044 Uiso 1 1 calc R U . . .
H12B H 0.290623 0.377500 0.762736 0.044 Uiso 1 1 calc R U . . .
H12C H 0.649449 0.284362 0.759533 0.044 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
C1 C6 1.404(5) . ?
C1 N1 1.404(5) . ?
C1 C2 1.413(5) . ?
C2 C3 1.401(5) . ?
C2 C7 1.483(5) . ?
C3 C4 1.381(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.402(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.219(4) . ?
C7 C8 1.492(5) . ?
C8 C9 1.340(5) . ?
C8 C11 1.516(5) . ?
C9 C10 1.479(5) . ?
C9 H9 0.9500 . ?
C10 O2 1.237(4) . ?
C10 N1 1.345(5) . ?
N1 H1N 0.88(6) . ?
C11 O3 1.202(5) . ?
C11 O4 1.321(4) . ?
O4 C12 1.453(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
C6 C1 N1 115.6(3) . . ?
C6 C1 C2 118.9(3) . . ?
N1 C1 C2 125.2(3) . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 C7 115.9(3) . . ?
C1 C2 C7 125.5(3) . . ?
C4 C3 C2 121.9(3) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 121.3(3) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
O1 C7 C2 120.9(3) . . ?
O1 C7 C8 119.3(3) . . ?
C2 C7 C8 119.7(3) . . ?
C9 C8 C7 125.3(3) . . ?
C9 C8 C11 116.4(3) . . ?
C7 C8 C11 118.3(3) . . ?
C8 C9 C10 129.2(3) . . ?
C8 C9 H9 115.4 . . ?
C10 C9 H9 115.4 . . ?
O2 C10 N1 120.8(3) . . ?
O2 C10 C9 117.5(3) . . ?
N1 C10 C9 121.6(3) . . ?
C10 N1 C1 132.8(3) . . ?
C10 N1 H1N 113(4) . . ?
C1 N1 H1N 114(4) . . ?
O3 C11 O4 126.0(3) . . ?
O3 C11 C8 122.7(3) . . ?
O4 C11 C8 111.2(3) . . ?
C11 O4 C12 115.7(3) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C6 C1 C2 C3 -0.2(5) . . . . ?
N1 C1 C2 C3 173.7(3) . . . . ?
C6 C1 C2 C7 -178.7(3) . . . . ?
N1 C1 C2 C7 -4.8(6) . . . . ?
C1 C2 C3 C4 1.7(6) . . . . ?
C7 C2 C3 C4 -179.7(3) . . . . ?
C2 C3 C4 C5 -1.5(6) . . . . ?
C3 C4 C5 C6 -0.3(6) . . . . ?
C4 C5 C6 C1 1.8(6) . . . . ?
N1 C1 C6 C5 -176.0(3) . . . . ?
C2 C1 C6 C5 -1.6(5) . . . . ?
C3 C2 C7 O1 -32.7(5) . . . . ?
C1 C2 C7 O1 145.8(4) . . . . ?
C3 C2 C7 C8 143.4(3) . . . . ?
C1 C2 C7 C8 -38.1(5) . . . . ?
O1 C7 C8 C9 -142.1(4) . . . . ?
C2 C7 C8 C9 41.6(5) . . . . ?
O1 C7 C8 C11 35.0(5) . . . . ?
C2 C7 C8 C11 -141.3(3) . . . . ?
C7 C8 C9 C10 3.2(6) . . . . ?
C11 C8 C9 C10 -173.9(3) . . . . ?
C8 C9 C10 O2 149.2(4) . . . . ?
C8 C9 C10 N1 -32.7(6) . . . . ?
O2 C10 N1 C1 -175.8(4) . . . . ?
C9 C10 N1 C1 6.1(6) . . . . ?
C6 C1 N1 C10 -161.2(4) . . . . ?
C2 C1 N1 C10 24.8(6) . . . . ?
C9 C8 C11 O3 26.4(5) . . . . ?
C7 C8 C11 O3 -151.0(4) . . . . ?
C9 C8 C11 O4 -152.2(3) . . . . ?
C7 C8 C11 O4 30.4(5) . . . . ?
O3 C11 O4 C12 1.2(6) . . . . ?
C8 C11 O4 C12 179.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O2 0.88(6) 1.99(6) 2.866(4) 175(5) 3_766 yes

_refine_diff_density_max         0.339
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.094

####################################################################### 
# 
# 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_dbt4
_database_code_depnum_ccdc_archive 'CCDC 2361038'
loop_
_audit_author_name
_audit_author_address
'Robert Gyepes'
;Department of Inorganic Chemistry, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2024-06-06 deposited with the CCDC.	2024-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H13 N O5'
_chemical_formula_sum            'C13 H13 N O5'
_chemical_formula_weight         263.24

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'

_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                   5.6430(2)
_cell_length_b                   8.2097(3)
_cell_length_c                   13.1949(5)
_cell_angle_alpha                83.666(2)
_cell_angle_beta                 84.0290(10)
_cell_angle_gamma                78.499(2)
_cell_volume                     593.24(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5944
_cell_measurement_theta_min      2.5425
_cell_measurement_theta_max      27.4505

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_F_000             276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.464
_exptl_crystal_size_mid          0.252
_exptl_crystal_size_min          0.064
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device       'Bruker D8 VENTURE'
_diffrn_measurement_device_type  'κ-geometry diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10172
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.543
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2721
_reflns_number_gt                2506
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0301P)²+0.3263P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_number_reflns         2721
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0961(2) 0.48146(16) 0.68389(10) 0.0164(3) Uani 1 1 d . . . . .
C2 C 0.0908(2) 0.42707(16) 0.78860(10) 0.0168(3) Uani 1 1 d . . . . .
C3 C -0.1197(3) 0.48293(17) 0.85132(11) 0.0202(3) Uani 1 1 d . . . . .
H3 H -0.125622 0.447371 0.922381 0.024 Uiso 1 1 calc R U . . .
C4 C -0.3180(3) 0.58804(18) 0.81241(12) 0.0231(3) Uani 1 1 d . . . . .
H4 H -0.459581 0.622897 0.856155 0.028 Uiso 1 1 calc R U . . .
C5 C -0.3100(3) 0.64287(18) 0.70882(12) 0.0239(3) Uani 1 1 d . . . . .
H5 H -0.445306 0.716499 0.681624 0.029 Uiso 1 1 calc R U . . .
C6 C -0.1049(3) 0.58998(17) 0.64572(11) 0.0210(3) Uani 1 1 d . . . . .
H6 H -0.100122 0.628033 0.575013 0.025 Uiso 1 1 calc R U . . .
C7 C 0.2977(2) 0.32179(17) 0.83795(10) 0.0173(3) Uani 1 1 d . . . . .
O1 O 0.3038(2) 0.35406(13) 0.93490(7) 0.0230(2) Uani 1 1 d . . . . .
H1 H 0.440(4) 0.282(3) 0.9541(15) 0.035 Uiso 1 1 d . U . . .
C8 C 0.4652(2) 0.20015(16) 0.79387(10) 0.0164(3) Uani 1 1 d . . . . .
C9 C 0.4429(2) 0.15655(16) 0.68843(10) 0.0150(3) Uani 1 1 d . . . . .
H9 H 0.574475 0.059477 0.672376 0.018 Uiso 1 1 calc R U . . .
O2 O 0.21469(17) 0.10871(12) 0.68691(7) 0.0179(2) Uani 1 1 d . . . . .
C10 C 0.4715(2) 0.30361(16) 0.60947(9) 0.0154(3) Uani 1 1 d . . . . .
N1 N 0.2996(2) 0.44327(14) 0.61324(8) 0.0167(2) Uani 1 1 d . . . . .
H1N H 0.314(3) 0.520(2) 0.5629(15) 0.030(5) Uiso 1 1 d . . . . .
O3 O 0.64380(18) 0.29352(12) 0.54364(7) 0.0201(2) Uani 1 1 d . . . . .
C11 C 0.6563(2) 0.10485(17) 0.85499(10) 0.0185(3) Uani 1 1 d . . . . .
O4 O 0.6804(2) 0.13219(13) 0.94306(8) 0.0259(2) Uani 1 1 d . . . . .
O5 O 0.80290(18) -0.01657(12) 0.80837(7) 0.0203(2) Uani 1 1 d . . . . .
C12 C 1.0006(3) -0.10993(19) 0.86546(12) 0.0253(3) Uani 1 1 d . . . . .
H12A H 1.100708 -0.033545 0.882365 0.038 Uiso 1 1 calc R U . . .
H12B H 1.100304 -0.194201 0.823888 0.038 Uiso 1 1 calc R U . . .
H12C H 0.934317 -0.165099 0.928695 0.038 Uiso 1 1 calc R U . . .
C13 C 0.1897(3) 0.04159(18) 0.59463(10) 0.0213(3) Uani 1 1 d . . . . .
H13A H 0.192708 0.128124 0.537324 0.032 Uiso 1 1 calc R U . . .
H13B H 0.035201 0.002627 0.600085 0.032 Uiso 1 1 calc R U . . .
H13C H 0.323871 -0.052257 0.582868 0.032 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
C1 C6 1.3965(19) . ?
C1 C2 1.4036(18) . ?
C1 N1 1.4085(17) . ?
C2 C3 1.4028(19) . ?
C2 C7 1.4716(19) . ?
C3 C4 1.377(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.3400(15) . ?
C7 C8 1.3662(19) . ?
O1 H1 0.91(2) . ?
C8 C11 1.4597(18) . ?
C8 C9 1.4981(17) . ?
C9 O2 1.4217(15) . ?
C9 C10 1.5280(17) . ?
C9 H9 1.0000 . ?
O2 C13 1.4216(15) . ?
C10 O3 1.2306(16) . ?
C10 N1 1.3483(17) . ?
N1 H1N 0.87(2) . ?
C11 O4 1.2337(17) . ?
C11 O5 1.3254(17) . ?
O5 C12 1.4513(16) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
C6 C1 C2 119.49(12) . . ?
C6 C1 N1 115.97(12) . . ?
C2 C1 N1 124.39(12) . . ?
C3 C2 C1 118.29(13) . . ?
C3 C2 C7 117.68(12) . . ?
C1 C2 C7 123.95(12) . . ?
C4 C3 C2 121.63(13) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 119.67(13) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 119.75(13) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 121.17(13) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
O1 C7 C8 121.88(12) . . ?
O1 C7 C2 112.50(12) . . ?
C8 C7 C2 125.59(12) . . ?
C7 O1 H1 102.1(12) . . ?
C7 C8 C11 118.29(12) . . ?
C7 C8 C9 120.93(12) . . ?
C11 C8 C9 120.62(12) . . ?
O2 C9 C8 108.63(10) . . ?
O2 C9 C10 111.68(10) . . ?
C8 C9 C10 110.49(10) . . ?
O2 C9 H9 108.7 . . ?
C8 C9 H9 108.7 . . ?
C10 C9 H9 108.7 . . ?
C13 O2 C9 113.09(10) . . ?
O3 C10 N1 121.26(12) . . ?
O3 C10 C9 120.97(12) . . ?
N1 C10 C9 117.76(11) . . ?
C10 N1 C1 129.84(12) . . ?
C10 N1 H1N 114.9(12) . . ?
C1 N1 H1N 115.2(12) . . ?
O4 C11 O5 122.05(13) . . ?
O4 C11 C8 123.61(13) . . ?
O5 C11 C8 114.34(11) . . ?
C11 O5 C12 115.82(11) . . ?
O5 C12 H12A 109.5 . . ?
O5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C6 C1 C2 C3 0.75(19) . . . . ?
N1 C1 C2 C3 176.20(12) . . . . ?
C6 C1 C2 C7 -175.87(13) . . . . ?
N1 C1 C2 C7 -0.4(2) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C7 C2 C3 C4 177.03(12) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C2 C1 C6 C5 -0.9(2) . . . . ?
N1 C1 C6 C5 -176.75(12) . . . . ?
C3 C2 C7 O1 -28.82(17) . . . . ?
C1 C2 C7 O1 147.82(13) . . . . ?
C3 C2 C7 C8 149.43(13) . . . . ?
C1 C2 C7 C8 -33.9(2) . . . . ?
O1 C7 C8 C11 -0.55(19) . . . . ?
C2 C7 C8 C11 -178.65(12) . . . . ?
O1 C7 C8 C9 174.83(12) . . . . ?
C2 C7 C8 C9 -3.3(2) . . . . ?
C7 C8 C9 O2 -57.57(16) . . . . ?
C11 C8 C9 O2 117.71(13) . . . . ?
C7 C8 C9 C10 65.27(16) . . . . ?
C11 C8 C9 C10 -119.46(13) . . . . ?
C8 C9 O2 C13 -171.36(11) . . . . ?
C10 C9 O2 C13 66.54(14) . . . . ?
O2 C9 C10 O3 -123.61(13) . . . . ?
C8 C9 C10 O3 115.35(13) . . . . ?
O2 C9 C10 N1 55.16(15) . . . . ?
C8 C9 C10 N1 -65.87(15) . . . . ?
O3 C10 N1 C1 -177.31(12) . . . . ?
C9 C10 N1 C1 3.9(2) . . . . ?
C6 C1 N1 C10 -149.79(14) . . . . ?
C2 C1 N1 C10 34.6(2) . . . . ?
C7 C8 C11 O4 -2.8(2) . . . . ?
C9 C8 C11 O4 -178.22(12) . . . . ?
C7 C8 C11 O5 176.45(12) . . . . ?
C9 C8 C11 O5 1.05(17) . . . . ?
O4 C11 O5 C12 -2.93(18) . . . . ?
C8 C11 O5 C12 177.79(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O4 0.91(2) 1.64(2) 2.5114(15) 157.4(19) . yes
N1 H1N O3 0.87(2) 2.00(2) 2.8648(15) 174.9(17) 2_666 yes

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_dbt8
_database_code_depnum_ccdc_archive 'CCDC 2361035'
loop_
_audit_author_name
_audit_author_address
'Robert Gyepes'
;Department of Inorganic Chemistry, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2024-06-06 deposited with the CCDC.	2024-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 N O5 S'
_chemical_formula_sum            'C14 H13 N O5 S'
_chemical_formula_weight         307.31

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.3101(3)
_cell_length_b                   5.9917(2)
_cell_length_c                   28.0633(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.213(2)
_cell_angle_gamma                90
_cell_volume                     1382.99(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6520
_cell_measurement_theta_min      3.1822
_cell_measurement_theta_max      69.9256

_exptl_crystal_description       needle
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    2.294
_shelx_estimated_absorpt_T_min   0.551
_shelx_estimated_absorpt_T_max   0.843
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_T_max  0.84
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device       'Bruker D8 VENTURE'
_diffrn_measurement_device_type  'κ-geometry diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17824
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_av_R_equivalents  0.0791
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.182
_diffrn_reflns_theta_max         70.125
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2625
_reflns_number_gt                2198
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0410P)²+2.4722P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_number_reflns         2625
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1206
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7098(3) 0.8735(4) 0.46191(9) 0.0181(5) Uani 1 1 d . . . . .
C2 C 0.8074(3) 0.9057(4) 0.42536(9) 0.0194(5) Uani 1 1 d . . . . .
C3 C 0.9048(3) 1.0985(5) 0.42703(9) 0.0227(6) Uani 1 1 d . . . . .
H3 H 0.971169 1.122528 0.402617 0.027 Uiso 1 1 calc R U . . .
C4 C 0.9057(3) 1.2528(5) 0.46339(10) 0.0249(6) Uani 1 1 d . . . . .
H4 H 0.969174 1.384582 0.463270 0.030 Uiso 1 1 calc R U . . .
C5 C 0.8136(3) 1.2159(5) 0.50029(9) 0.0230(6) Uani 1 1 d . . . . .
H5 H 0.817027 1.319916 0.525960 0.028 Uiso 1 1 calc R U . . .
C6 C 0.7173(3) 1.0279(5) 0.49961(9) 0.0203(5) Uani 1 1 d . . . . .
H6 H 0.655273 1.002909 0.525042 0.024 Uiso 1 1 calc R U . . .
C7 C 0.8203(3) 0.7391(5) 0.38788(9) 0.0203(5) Uani 1 1 d . . . . .
O1 O 0.9725(2) 0.7231(4) 0.37698(7) 0.0261(4) Uani 1 1 d . . . . .
H1 H 0.972(4) 0.611(7) 0.3563(13) 0.039 Uiso 1 1 d . U . . .
C8 C 0.6934(3) 0.6178(4) 0.36583(9) 0.0192(5) Uani 1 1 d . . . . .
C9 C 0.5240(3) 0.6467(5) 0.37831(9) 0.0194(5) Uani 1 1 d . . . . .
H9 H 0.450889 0.545041 0.356801 0.023 Uiso 1 1 calc R U . . .
S1 S 0.44273(8) 0.92970(11) 0.36888(2) 0.02226(19) Uani 1 1 d . . . . .
C10 C 0.5155(3) 0.5759(4) 0.42967(9) 0.0187(5) Uani 1 1 d . . . . .
O2 O 0.4244(2) 0.4242(3) 0.43861(6) 0.0240(4) Uani 1 1 d . . . . .
C11 C 0.7228(3) 0.4555(5) 0.32933(9) 0.0203(5) Uani 1 1 d . . . . .
O3 O 0.8589(2) 0.4126(3) 0.31904(7) 0.0260(4) Uani 1 1 d . . . . .
O4 O 0.5891(2) 0.3557(3) 0.30708(6) 0.0231(4) Uani 1 1 d . . . . .
C12 C 0.6156(4) 0.1897(5) 0.27146(10) 0.0292(6) Uani 1 1 d . . . . .
H12A H 0.677130 0.256527 0.247768 0.044 Uiso 1 1 calc R U . . .
H12B H 0.510553 0.136197 0.255159 0.044 Uiso 1 1 calc R U . . .
H12C H 0.677141 0.064248 0.287349 0.044 Uiso 1 1 calc R U . . .
C13 C 0.2707(3) 0.8761(5) 0.32473(10) 0.0243(6) Uani 1 1 d . . . . .
O5 O 0.2329(2) 0.6911(4) 0.30974(7) 0.0315(5) Uani 1 1 d . . . . .
C14 C 0.1804(4) 1.0855(5) 0.30829(11) 0.0322(7) Uani 1 1 d . . . . .
H14A H 0.185132 1.108977 0.273958 0.048 Uiso 1 1 calc R U . . .
H14B H 0.230317 1.212891 0.326706 0.048 Uiso 1 1 calc R U . . .
H14C H 0.066650 1.071513 0.313467 0.048 Uiso 1 1 calc R U . . .
N1 N 0.6116(3) 0.6853(4) 0.46534(8) 0.0194(5) Uani 1 1 d . . . . .
H1N H 0.600(4) 0.659(5) 0.4928(12) 0.024(8) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.400(4) . ?
C1 N1 1.403(3) . ?
C1 C2 1.409(3) . ?
C2 C3 1.407(4) . ?
C2 C7 1.465(4) . ?
C3 C4 1.376(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.347(3) . ?
C7 C8 1.355(4) . ?
O1 H1 0.89(4) . ?
C8 C11 1.458(4) . ?
C8 C9 1.508(3) . ?
C9 C10 1.514(3) . ?
C9 S1 1.831(3) . ?
C9 H9 1.0000 . ?
S1 C13 1.782(3) . ?
C10 O2 1.231(3) . ?
C10 N1 1.357(3) . ?
C11 O3 1.234(3) . ?
C11 O4 1.336(3) . ?
O4 C12 1.449(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 O5 1.211(4) . ?
C13 C14 1.500(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N1 H1N 0.81(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 N1 116.2(2) . . ?
C6 C1 C2 119.5(2) . . ?
N1 C1 C2 124.1(2) . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 C7 118.9(2) . . ?
C1 C2 C7 122.6(2) . . ?
C4 C3 C2 121.2(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.8(2) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O1 C7 C8 123.6(2) . . ?
O1 C7 C2 112.3(2) . . ?
C8 C7 C2 124.1(2) . . ?
C7 O1 H1 107(2) . . ?
C7 C8 C11 118.7(2) . . ?
C7 C8 C9 121.6(2) . . ?
C11 C8 C9 119.7(2) . . ?
C8 C9 C10 111.2(2) . . ?
C8 C9 S1 114.21(18) . . ?
C10 C9 S1 109.31(17) . . ?
C8 C9 H9 107.3 . . ?
C10 C9 H9 107.3 . . ?
S1 C9 H9 107.3 . . ?
C13 S1 C9 100.17(13) . . ?
O2 C10 N1 121.4(2) . . ?
O2 C10 C9 121.0(2) . . ?
N1 C10 C9 117.7(2) . . ?
O3 C11 O4 121.8(2) . . ?
O3 C11 C8 123.7(2) . . ?
O4 C11 C8 114.6(2) . . ?
C11 O4 C12 115.6(2) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C13 C14 124.4(3) . . ?
O5 C13 S1 123.3(2) . . ?
C14 C13 S1 112.3(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 N1 C1 128.6(2) . . ?
C10 N1 H1N 118(2) . . ?
C1 N1 H1N 112(2) . . ?

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
C6 C1 C2 C3 -2.6(4) . . . . ?
N1 C1 C2 C3 -177.8(2) . . . . ?
C6 C1 C2 C7 172.8(2) . . . . ?
N1 C1 C2 C7 -2.4(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C7 C2 C3 C4 -175.5(2) . . . . ?
C2 C3 C4 C5 2.3(4) . . . . ?
C3 C4 C5 C6 -2.1(4) . . . . ?
C4 C5 C6 C1 -0.5(4) . . . . ?
N1 C1 C6 C5 178.4(2) . . . . ?
C2 C1 C6 C5 2.8(4) . . . . ?
C3 C2 C7 O1 34.1(3) . . . . ?
C1 C2 C7 O1 -141.3(2) . . . . ?
C3 C2 C7 C8 -144.6(3) . . . . ?
C1 C2 C7 C8 40.0(4) . . . . ?
O1 C7 C8 C11 2.1(4) . . . . ?
C2 C7 C8 C11 -179.4(2) . . . . ?
O1 C7 C8 C9 -178.2(2) . . . . ?
C2 C7 C8 C9 0.3(4) . . . . ?
C7 C8 C9 C10 -65.1(3) . . . . ?
C11 C8 C9 C10 114.7(3) . . . . ?
C7 C8 C9 S1 59.2(3) . . . . ?
C11 C8 C9 S1 -121.1(2) . . . . ?
C8 C9 S1 C13 118.48(19) . . . . ?
C10 C9 S1 C13 -116.27(18) . . . . ?
C8 C9 C10 O2 -119.9(3) . . . . ?
S1 C9 C10 O2 113.2(2) . . . . ?
C8 C9 C10 N1 60.1(3) . . . . ?
S1 C9 C10 N1 -66.9(3) . . . . ?
C7 C8 C11 O3 4.1(4) . . . . ?
C9 C8 C11 O3 -175.6(2) . . . . ?
C7 C8 C11 O4 -175.3(2) . . . . ?
C9 C8 C11 O4 4.9(3) . . . . ?
O3 C11 O4 C12 1.9(4) . . . . ?
C8 C11 O4 C12 -178.6(2) . . . . ?
C9 S1 C13 O5 1.5(3) . . . . ?
C9 S1 C13 C14 -178.05(19) . . . . ?
O2 C10 N1 C1 -173.4(2) . . . . ?
C9 C10 N1 C1 6.6(4) . . . . ?
C6 C1 N1 C10 142.9(3) . . . . ?
C2 C1 N1 C10 -41.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O3 0.89(4) 1.76(4) 2.561(3) 148(3) . yes
C9 H9 O4 1.00 2.24 2.764(3) 111 . yes
C9 H9 O5 1.00 2.26 2.881(3) 119.0 . yes
C12 H12B O5 0.98 2.54 3.420(4) 149 2_545 yes
C14 H14A O5 0.98 2.58 3.546(4) 167 2 yes
N1 H1N O2 0.81(3) 2.02(3) 2.831(3) 177(3) 3_666 yes

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_dbt5
_database_code_depnum_ccdc_archive 'CCDC 2361037'
loop_
_audit_author_name
_audit_author_address
'Robert Gyepes'
;Department of Inorganic Chemistry, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2024-06-06 deposited with the CCDC.	2024-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 N O5'
_chemical_formula_sum            'C16 H19 N O5'
_chemical_formula_weight         305.32

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.5277(3)
_cell_length_b                   13.5344(5)
_cell_length_c                   17.0980(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.093(2)
_cell_angle_gamma                90
_cell_volume                     1491.60(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9932
_cell_measurement_theta_min      2.8438
_cell_measurement_theta_max      27.4672

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.558
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.177
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device       'Bruker D8 VENTURE'
_diffrn_measurement_device_type  'κ-geometry diffractometer'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16531
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.928
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3430
_reflns_number_gt                3146
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0298P)²+0.7760P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_number_reflns         3430
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0857
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.77164(17) 0.48804(8) 0.36227(7) 0.0159(2) Uani 1 1 d . . . . .
C2 C 0.75054(18) 0.50603(8) 0.28038(7) 0.0161(2) Uani 1 1 d . . . . .
C3 C 0.90689(19) 0.47101(9) 0.23956(7) 0.0201(2) Uani 1 1 d . . . . .
H3 H 0.895069 0.482861 0.184268 0.024 Uiso 1 1 calc R U . . .
C4 C 1.0769(2) 0.41996(9) 0.27753(8) 0.0234(3) Uani 1 1 d . . . . .
H4 H 1.182238 0.398474 0.248951 0.028 Uiso 1 1 calc R U . . .
C5 C 1.0924(2) 0.40024(9) 0.35815(8) 0.0238(3) Uani 1 1 d . . . . .
H5 H 1.207284 0.363796 0.384582 0.029 Uiso 1 1 calc R U . . .
C6 C 0.94121(19) 0.43356(9) 0.39978(7) 0.0206(2) Uani 1 1 d . . . . .
H6 H 0.952517 0.419265 0.454698 0.025 Uiso 1 1 calc R U . . .
C7 C 0.56739(18) 0.55254(8) 0.23374(7) 0.0167(2) Uani 1 1 d . . . . .
O1 O 0.53063(15) 0.51873(7) 0.15915(5) 0.0233(2) Uani 1 1 d . . . . .
H1 H 0.411(3) 0.5531(13) 0.1359(10) 0.035 Uiso 1 1 d . U . . .
C8 C 0.44461(18) 0.62254(8) 0.26053(6) 0.0157(2) Uani 1 1 d . . . . .
C9 C 0.50505(17) 0.66834(8) 0.34085(6) 0.0145(2) Uani 1 1 d . . . . .
H9 H 0.408088 0.723999 0.346977 0.017 Uiso 1 1 calc R U . . .
O2 O 0.71018(12) 0.70604(6) 0.34640(4) 0.01599(17) Uani 1 1 d . . . . .
C10 C 0.49351(17) 0.59227(8) 0.40572(6) 0.0155(2) Uani 1 1 d . . . . .
N1 N 0.62315(15) 0.51387(7) 0.41011(6) 0.0167(2) Uani 1 1 d . . . . .
H1N H 0.625(2) 0.4780(12) 0.4534(9) 0.026(4) Uiso 1 1 d . . . . .
O3 O 0.37260(13) 0.60291(6) 0.45361(5) 0.02074(19) Uani 1 1 d . . . . .
C11 C 0.25882(18) 0.65500(8) 0.20786(7) 0.0171(2) Uani 1 1 d . . . . .
O4 O 0.21443(14) 0.62894(7) 0.13827(5) 0.0244(2) Uani 1 1 d . . . . .
O5 O 0.13639(12) 0.71513(6) 0.24158(5) 0.01881(18) Uani 1 1 d . . . . .
C12 C -0.05383(18) 0.74567(10) 0.19178(7) 0.0220(3) Uani 1 1 d . . . . .
H12A H -0.020118 0.783828 0.146788 0.033 Uiso 1 1 calc R U . . .
H12B H -0.135523 0.786682 0.222666 0.033 Uiso 1 1 calc R U . . .
H12C H -0.134397 0.687132 0.172231 0.033 Uiso 1 1 calc R U . . .
C13 C 0.77176(18) 0.76251(9) 0.41699(7) 0.0184(2) Uani 1 1 d . . . . .
H13A H 0.753954 0.722802 0.464080 0.022 Uiso 1 1 calc R U . . .
H13B H 0.684690 0.822504 0.416208 0.022 Uiso 1 1 calc R U . . .
C14 C 0.99591(18) 0.79105(9) 0.42082(7) 0.0179(2) Uani 1 1 d . . . . .
H14A H 1.013227 0.827449 0.372065 0.022 Uiso 1 1 calc R U . . .
H14B H 1.081956 0.730550 0.423314 0.022 Uiso 1 1 calc R U . . .
C15 C 1.07064(19) 0.85535(9) 0.49271(7) 0.0211(2) Uani 1 1 d . . . . .
H15A H 1.061005 0.817254 0.541430 0.025 Uiso 1 1 calc R U . . .
H15B H 0.978364 0.913508 0.491920 0.025 Uiso 1 1 calc R U . . .
C16 C 1.2931(2) 0.89057(11) 0.49518(8) 0.0282(3) Uani 1 1 d . . . . .
H16A H 1.386560 0.833471 0.500195 0.042 Uiso 1 1 calc R U . . .
H16B H 1.331166 0.934563 0.540680 0.042 Uiso 1 1 calc R U . . .
H16C H 1.304714 0.926361 0.446246 0.042 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
C1 C6 1.3986(17) . ?
C1 C2 1.4063(16) . ?
C1 N1 1.4076(14) . ?
C2 C3 1.4066(16) . ?
C2 C7 1.4698(16) . ?
C3 C4 1.3793(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3920(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3807(17) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.3405(14) . ?
C7 C8 1.3660(16) . ?
O1 H1 0.942(18) . ?
C8 C11 1.4593(16) . ?
C8 C9 1.5015(15) . ?
C9 O2 1.4220(13) . ?
C9 C10 1.5239(15) . ?
C9 H9 1.0000 . ?
O2 C13 1.4315(13) . ?
C10 O3 1.2323(14) . ?
C10 N1 1.3519(15) . ?
N1 H1N 0.883(16) . ?
C11 O4 1.2310(14) . ?
C11 O5 1.3338(14) . ?
O5 C12 1.4503(14) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.5047(16) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5222(16) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5226(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C6 C1 C2 119.59(10) . . ?
C6 C1 N1 115.61(10) . . ?
C2 C1 N1 124.57(10) . . ?
C1 C2 C3 118.11(11) . . ?
C1 C2 C7 123.89(10) . . ?
C3 C2 C7 117.83(10) . . ?
C4 C3 C2 121.88(11) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 119.30(11) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.11(12) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.95(11) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
O1 C7 C8 121.97(11) . . ?
O1 C7 C2 112.21(10) . . ?
C8 C7 C2 125.82(10) . . ?
C7 O1 H1 104.2(10) . . ?
C7 C8 C11 118.45(10) . . ?
C7 C8 C9 120.64(10) . . ?
C11 C8 C9 120.85(10) . . ?
O2 C9 C8 108.53(9) . . ?
O2 C9 C10 110.37(9) . . ?
C8 C9 C10 110.53(9) . . ?
O2 C9 H9 109.1 . . ?
C8 C9 H9 109.1 . . ?
C10 C9 H9 109.1 . . ?
C9 O2 C13 112.57(8) . . ?
O3 C10 N1 121.06(10) . . ?
O3 C10 C9 121.01(10) . . ?
N1 C10 C9 117.92(10) . . ?
C10 N1 C1 130.18(10) . . ?
C10 N1 H1N 113.8(10) . . ?
C1 N1 H1N 115.5(10) . . ?
O4 C11 O5 121.81(11) . . ?
O4 C11 C8 123.78(11) . . ?
O5 C11 C8 114.41(10) . . ?
C11 O5 C12 115.85(9) . . ?
O5 C12 H12A 109.5 . . ?
O5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 C14 108.37(9) . . ?
O2 C13 H13A 110.0 . . ?
C14 C13 H13A 110.0 . . ?
O2 C13 H13B 110.0 . . ?
C14 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
C13 C14 C15 111.54(9) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C16 112.57(10) . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
C6 C1 C2 C3 -2.25(16) . . . . ?
N1 C1 C2 C3 -176.51(11) . . . . ?
C6 C1 C2 C7 172.89(11) . . . . ?
N1 C1 C2 C7 -1.37(18) . . . . ?
C1 C2 C3 C4 0.28(17) . . . . ?
C7 C2 C3 C4 -175.16(11) . . . . ?
C2 C3 C4 C5 1.59(19) . . . . ?
C3 C4 C5 C6 -1.46(19) . . . . ?
C4 C5 C6 C1 -0.53(19) . . . . ?
C2 C1 C6 C5 2.41(18) . . . . ?
N1 C1 C6 C5 177.17(11) . . . . ?
C1 C2 C7 O1 -148.04(11) . . . . ?
C3 C2 C7 O1 27.11(15) . . . . ?
C1 C2 C7 C8 32.17(18) . . . . ?
C3 C2 C7 C8 -152.68(11) . . . . ?
O1 C7 C8 C11 5.08(17) . . . . ?
C2 C7 C8 C11 -175.15(10) . . . . ?
O1 C7 C8 C9 -172.08(10) . . . . ?
C2 C7 C8 C9 7.69(17) . . . . ?
C7 C8 C9 O2 53.35(13) . . . . ?
C11 C8 C9 O2 -123.75(11) . . . . ?
C7 C8 C9 C10 -67.82(13) . . . . ?
C11 C8 C9 C10 115.09(11) . . . . ?
C8 C9 O2 C13 172.37(9) . . . . ?
C10 C9 O2 C13 -66.37(11) . . . . ?
O2 C9 C10 O3 122.32(11) . . . . ?
C8 C9 C10 O3 -117.61(12) . . . . ?
O2 C9 C10 N1 -56.30(13) . . . . ?
C8 C9 C10 N1 63.77(13) . . . . ?
O3 C10 N1 C1 -179.84(11) . . . . ?
C9 C10 N1 C1 -1.22(18) . . . . ?
C6 C1 N1 C10 151.16(12) . . . . ?
C2 C1 N1 C10 -34.37(19) . . . . ?
C7 C8 C11 O4 -6.07(17) . . . . ?
C9 C8 C11 O4 171.09(11) . . . . ?
C7 C8 C11 O5 173.00(10) . . . . ?
C9 C8 C11 O5 -9.84(15) . . . . ?
O4 C11 O5 C12 1.46(16) . . . . ?
C8 C11 O5 C12 -177.63(9) . . . . ?
C9 O2 C13 C14 174.96(9) . . . . ?
O2 C13 C14 C15 177.52(9) . . . . ?
C13 C14 C15 C16 -176.41(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O4 0.942(18) 1.648(18) 2.5258(13) 153.4(16) . yes
N1 H1N O3 0.883(16) 1.929(16) 2.8121(13) 178.6(15) 3_666 yes
C14 H14B O3 0.99 2.56 3.5225(14) 165 1_655 yes

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.039

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

data_dbt11
_database_code_depnum_ccdc_archive 'CCDC 2361039'
loop_
_audit_author_name
_audit_author_address
'Robert Gyepes'
;Department of Inorganic Chemistry, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2024-06-06 deposited with the CCDC.	2024-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 N O6 S'
_chemical_formula_sum            'C18 H15 N O6 S'
_chemical_formula_weight         373.37

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      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                   8.2738(4)
_cell_length_b                   9.7141(5)
_cell_length_c                   10.3106(5)
_cell_angle_alpha                79.4250(10)
_cell_angle_beta                 83.4650(10)
_cell_angle_gamma                80.5630(10)
_cell_volume                     800.59(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      4.3786
_cell_measurement_theta_max      72.1420

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.546
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.095
_exptl_absorpt_coefficient_mu    2.147
_shelx_estimated_absorpt_T_min   0.387
_shelx_estimated_absorpt_T_max   0.822
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_T_max  0.82
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device       'Bruker D8 VENTURE'
_diffrn_measurement_device_type  'κ-geometry diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17432
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.378
_diffrn_reflns_theta_max         72.135
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3118
_reflns_number_gt                3087
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0310P)²+0.4914P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_number_reflns         3118
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0810
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.70898(16) 0.48864(14) 0.24656(13) 0.0149(3) Uani 1 1 d . . . . .
C2 C 0.88101(16) 0.47301(13) 0.22205(13) 0.0147(3) Uani 1 1 d . . . . .
C3 C 0.95462(17) 0.38981(14) 0.12687(14) 0.0182(3) Uani 1 1 d . . . . .
H3 H 1.070859 0.377334 0.109370 0.022 Uiso 1 1 calc R U . . .
C4 C 0.86263(19) 0.32582(16) 0.05825(14) 0.0233(3) Uani 1 1 d . . . . .
H4 H 0.915280 0.269755 -0.005199 0.028 Uiso 1 1 calc R U . . .
C5 C 0.69289(19) 0.34395(17) 0.08258(15) 0.0251(3) Uani 1 1 d . . . . .
H5 H 0.628694 0.300755 0.035331 0.030 Uiso 1 1 calc R U . . .
C6 C 0.61692(18) 0.42506(16) 0.17581(14) 0.0202(3) Uani 1 1 d . . . . .
H6 H 0.500498 0.437505 0.191704 0.024 Uiso 1 1 calc R U . . .
C7 C 0.99187(16) 0.53259(14) 0.29197(13) 0.0144(3) Uani 1 1 d . . . . .
O1 O 1.14326(12) 0.45863(10) 0.28979(10) 0.0199(2) Uani 1 1 d . . . . .
H1 H 1.203(2) 0.508(2) 0.3361(19) 0.030 Uiso 1 1 d . U . . .
C8 C 0.95462(15) 0.65048(14) 0.35241(13) 0.0136(3) Uani 1 1 d . . . . .
C9 C 0.78716(15) 0.73870(13) 0.35771(13) 0.0135(3) Uani 1 1 d . . . . .
H9 H 0.790406 0.803245 0.422281 0.016 Uiso 1 1 calc R U . . .
S1 S 0.75496(4) 0.85445(3) 0.19900(3) 0.01528(11) Uani 1 1 d . . . . .
C10 C 0.65039(15) 0.65213(14) 0.41442(12) 0.0135(3) Uani 1 1 d . . . . .
N1 N 0.61861(14) 0.55269(12) 0.34973(11) 0.0151(2) Uani 1 1 d . . . . .
H1N H 0.541(2) 0.509(2) 0.3875(19) 0.026(5) Uiso 1 1 d . . . . .
O2 O 0.57285(11) 0.67297(10) 0.51981(9) 0.0170(2) Uani 1 1 d . . . . .
C11 C 1.08538(16) 0.69242(14) 0.41484(13) 0.0146(3) Uani 1 1 d . . . . .
O3 O 1.22802(11) 0.63051(10) 0.41269(10) 0.0198(2) Uani 1 1 d . . . . .
O4 O 1.03924(11) 0.80400(10) 0.47541(10) 0.0176(2) Uani 1 1 d . . . . .
C12 C 1.16675(17) 0.84719(15) 0.53880(14) 0.0198(3) Uani 1 1 d . . . . .
H12A H 1.195953 0.775978 0.616207 0.030 Uiso 1 1 calc R U . . .
H12B H 1.126000 0.938599 0.566943 0.030 Uiso 1 1 calc R U . . .
H12C H 1.264140 0.856086 0.475922 0.030 Uiso 1 1 calc R U . . .
O5 O 0.77727(13) 0.77031(11) 0.09566(10) 0.0227(2) Uani 1 1 d . . . . .
O6 O 0.85779(12) 0.96185(11) 0.19290(11) 0.0255(2) Uani 1 1 d . . . . .
C13 C 0.54675(16) 0.93206(14) 0.21297(13) 0.0144(3) Uani 1 1 d . . . . .
C14 C 0.50114(17) 1.05312(15) 0.26992(14) 0.0195(3) Uani 1 1 d . . . . .
H14 H 0.580498 1.092456 0.305712 0.023 Uiso 1 1 calc R U . . .
C15 C 0.33751(18) 1.11581(15) 0.27373(15) 0.0235(3) Uani 1 1 d . . . . .
H15 H 0.304030 1.198690 0.312321 0.028 Uiso 1 1 calc R U . . .
C16 C 0.22326(17) 1.05698(16) 0.22101(15) 0.0224(3) Uani 1 1 d . . . . .
H16 H 0.111803 1.100845 0.222655 0.027 Uiso 1 1 calc R U . . .
C17 C 0.26944(18) 0.93542(17) 0.16612(16) 0.0246(3) Uani 1 1 d . . . . .
H17 H 0.189722 0.895467 0.131398 0.030 Uiso 1 1 calc R U . . .
C18 C 0.43243(18) 0.87174(15) 0.16178(15) 0.0208(3) Uani 1 1 d . . . . .
H18 H 0.465253 0.788072 0.124320 0.025 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
C1 C6 1.3928(19) . ?
C1 C2 1.4051(19) . ?
C1 N1 1.4095(17) . ?
C2 C3 1.4074(19) . ?
C2 C7 1.4744(18) . ?
C3 C4 1.380(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.3379(16) . ?
C7 C8 1.3775(19) . ?
O1 H1 0.96(2) . ?
C8 C11 1.4663(18) . ?
C8 C9 1.5059(17) . ?
C9 C10 1.5201(17) . ?
C9 S1 1.8272(13) . ?
C9 H9 1.0000 . ?
S1 O5 1.4362(11) . ?
S1 O6 1.4391(11) . ?
S1 C13 1.7647(13) . ?
C10 O2 1.2300(16) . ?
C10 N1 1.3442(17) . ?
N1 H1N 0.85(2) . ?
C11 O3 1.2334(16) . ?
C11 O4 1.3301(17) . ?
O4 C12 1.4557(16) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.3876(19) . ?
C13 C14 1.3884(19) . ?
C14 C15 1.390(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(2) . ?
C17 H17 0.9500 . ?
C18 H18 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
C6 C1 C2 120.00(12) . . ?
C6 C1 N1 114.91(12) . . ?
C2 C1 N1 124.73(12) . . ?
C1 C2 C3 117.80(12) . . ?
C1 C2 C7 125.10(12) . . ?
C3 C2 C7 117.06(12) . . ?
C4 C3 C2 121.83(13) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 119.53(13) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 119.96(13) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.86(13) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O1 C7 C8 120.98(12) . . ?
O1 C7 C2 111.75(11) . . ?
C8 C7 C2 127.27(12) . . ?
C7 O1 H1 103.9(12) . . ?
C7 C8 C11 118.15(11) . . ?
C7 C8 C9 123.61(12) . . ?
C11 C8 C9 118.24(11) . . ?
C8 C9 C10 113.03(10) . . ?
C8 C9 S1 110.44(9) . . ?
C10 C9 S1 115.75(9) . . ?
C8 C9 H9 105.6 . . ?
C10 C9 H9 105.6 . . ?
S1 C9 H9 105.6 . . ?
O5 S1 O6 119.26(7) . . ?
O5 S1 C13 108.19(6) . . ?
O6 S1 C13 109.13(6) . . ?
O5 S1 C9 109.33(6) . . ?
O6 S1 C9 104.94(6) . . ?
C13 S1 C9 105.10(6) . . ?
O2 C10 N1 121.35(12) . . ?
O2 C10 C9 119.25(12) . . ?
N1 C10 C9 119.40(11) . . ?
C10 N1 C1 131.77(12) . . ?
C10 N1 H1N 113.8(13) . . ?
C1 N1 H1N 113.1(13) . . ?
O3 C11 O4 121.51(12) . . ?
O3 C11 C8 123.60(12) . . ?
O4 C11 C8 114.90(11) . . ?
C11 O4 C12 115.92(10) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 121.47(12) . . ?
C18 C13 S1 118.27(10) . . ?
C14 C13 S1 120.23(10) . . ?
C13 C14 C15 118.93(13) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C16 C15 C14 119.78(13) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 120.86(13) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 119.92(13) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 119.03(13) . . ?
C13 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?

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
C6 C1 C2 C3 -1.22(19) . . . . ?
N1 C1 C2 C3 171.48(12) . . . . ?
C6 C1 C2 C7 -178.75(13) . . . . ?
N1 C1 C2 C7 -6.1(2) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C7 C2 C3 C4 178.22(13) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
C2 C1 C6 C5 1.2(2) . . . . ?
N1 C1 C6 C5 -172.22(13) . . . . ?
C1 C2 C7 O1 154.80(12) . . . . ?
C3 C2 C7 O1 -22.75(16) . . . . ?
C1 C2 C7 C8 -26.3(2) . . . . ?
C3 C2 C7 C8 156.16(13) . . . . ?
O1 C7 C8 C11 -0.24(19) . . . . ?
C2 C7 C8 C11 -179.06(12) . . . . ?
O1 C7 C8 C9 179.66(11) . . . . ?
C2 C7 C8 C9 0.8(2) . . . . ?
C7 C8 C9 C10 53.82(17) . . . . ?
C11 C8 C9 C10 -126.27(12) . . . . ?
C7 C8 C9 S1 -77.64(14) . . . . ?
C11 C8 C9 S1 102.26(12) . . . . ?
C8 C9 S1 O5 56.37(10) . . . . ?
C10 C9 S1 O5 -73.67(11) . . . . ?
C8 C9 S1 O6 -72.66(10) . . . . ?
C10 C9 S1 O6 157.31(10) . . . . ?
C8 C9 S1 C13 172.29(9) . . . . ?
C10 C9 S1 C13 42.26(11) . . . . ?
C8 C9 C10 O2 115.03(13) . . . . ?
S1 C9 C10 O2 -116.20(12) . . . . ?
C8 C9 C10 N1 -63.78(15) . . . . ?
S1 C9 C10 N1 65.00(14) . . . . ?
O2 C10 N1 C1 -164.45(13) . . . . ?
C9 C10 N1 C1 14.3(2) . . . . ?
C6 C1 N1 C10 -160.00(14) . . . . ?
C2 C1 N1 C10 27.0(2) . . . . ?
C7 C8 C11 O3 2.3(2) . . . . ?
C9 C8 C11 O3 -177.62(12) . . . . ?
C7 C8 C11 O4 -177.66(11) . . . . ?
C9 C8 C11 O4 2.43(17) . . . . ?
O3 C11 O4 C12 -0.29(18) . . . . ?
C8 C11 O4 C12 179.67(11) . . . . ?
O5 S1 C13 C18 19.94(13) . . . . ?
O6 S1 C13 C18 151.13(11) . . . . ?
C9 S1 C13 C18 -96.77(12) . . . . ?
O5 S1 C13 C14 -157.93(11) . . . . ?
O6 S1 C13 C14 -26.75(13) . . . . ?
C9 S1 C13 C14 85.35(12) . . . . ?
C18 C13 C14 C15 -0.9(2) . . . . ?
S1 C13 C14 C15 176.89(11) . . . . ?
C13 C14 C15 C16 0.0(2) . . . . ?
C14 C15 C16 C17 0.9(2) . . . . ?
C15 C16 C17 C18 -0.8(2) . . . . ?
C14 C13 C18 C17 1.0(2) . . . . ?
S1 C13 C18 C17 -176.89(11) . . . . ?
C16 C17 C18 C13 -0.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O3 0.96(2) 1.60(2) 2.4996(14) 155.5(18) . yes
C9 H9 O4 1.00 2.19 2.7419(16) 113.0 . yes
N1 H1N O2 0.85(2) 2.16(2) 2.9488(15) 156.1(17) 2_666 yes
C12 H12B O4 0.98 2.63 3.5196(17) 150.8 2_776 yes

_refine_diff_density_max         0.402
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_dbt7
_database_code_depnum_ccdc_archive 'CCDC 2361036'
loop_
_audit_author_name
_audit_author_address
'Robert Gyepes'
;Department of Inorganic Chemistry, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2024-06-06 deposited with the CCDC.	2024-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 Cl N2 O4, C2 H3 N'
_chemical_formula_sum            'C20 H18 Cl N3 O4'
_chemical_formula_weight         399.82

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'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.6021(9)
_cell_length_b                   24.331(2)
_cell_length_c                   7.7431(7)
_cell_angle_alpha                90
_cell_angle_beta                 110.933(6)
_cell_angle_gamma                90
_cell_volume                     1865.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1947
_cell_measurement_theta_min      3.6333
_cell_measurement_theta_max      68.1974

_exptl_crystal_description       prism
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.077
_exptl_absorpt_coefficient_mu    2.098
_shelx_estimated_absorpt_T_min   0.787
_shelx_estimated_absorpt_T_max   0.855
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device       'Bruker D8 VENTURE'
_diffrn_measurement_device_type  'κ-geometry diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16741
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_av_R_equivalents  0.1219
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.633
_diffrn_reflns_theta_max         68.357
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3413
_reflns_number_gt                2275
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0531P)²+0.1043P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_number_reflns         3413
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7120(3) 0.37353(11) 0.9704(4) 0.0199(6) Uani 1 1 d . . . . .
C2 C 0.6467(3) 0.41890(11) 0.8636(4) 0.0199(6) Uani 1 1 d . . . . .
C3 C 0.6525(3) 0.46966(11) 0.9499(4) 0.0244(6) Uani 1 1 d . . . . .
H3 H 0.607727 0.500344 0.878121 0.029 Uiso 1 1 calc R U . . .
C4 C 0.7215(3) 0.47635(11) 1.1367(4) 0.0255(6) Uani 1 1 d . . . . .
H4 H 0.724046 0.511189 1.193215 0.031 Uiso 1 1 calc R U . . .
C5 C 0.7871(3) 0.43160(12) 1.2411(4) 0.0271(6) Uani 1 1 d . . . . .
H5 H 0.836306 0.436008 1.369555 0.033 Uiso 1 1 calc R U . . .
C6 C 0.7815(3) 0.38081(11) 1.1602(4) 0.0245(6) Uani 1 1 d . . . . .
H6 H 0.825317 0.350344 1.234052 0.029 Uiso 1 1 calc R U . . .
C7 C 0.5653(3) 0.41543(11) 0.6658(4) 0.0203(6) Uani 1 1 d . . . . .
O1 O 0.4614(2) 0.45095(8) 0.6169(3) 0.0261(5) Uani 1 1 d . . . . .
H1 H 0.416(3) 0.4488(14) 0.494(5) 0.039 Uiso 1 1 d . U . . .
C8 C 0.5900(3) 0.38113(11) 0.5418(4) 0.0200(6) Uani 1 1 d . . . . .
C9 C 0.7107(3) 0.34337(11) 0.5961(4) 0.0196(6) Uani 1 1 d . . . . .
H9 H 0.708891 0.323229 0.482668 0.023 Uiso 1 1 calc R U . . .
N2 N 0.8381(2) 0.37349(9) 0.6680(3) 0.0212(5) Uani 1 1 d . . . . .
H2N H 0.828(3) 0.4109(15) 0.663(4) 0.036(9) Uiso 1 1 d . . . . .
C10 C 0.7000(3) 0.30081(11) 0.7357(4) 0.0202(6) Uani 1 1 d . . . . .
N1 N 0.7031(2) 0.31909(9) 0.9029(3) 0.0207(5) Uani 1 1 d . . . . .
H1N H 0.702(3) 0.2954(13) 0.981(4) 0.027(8) Uiso 1 1 d . . . . .
O2 O 0.68946(19) 0.25146(7) 0.6991(3) 0.0247(4) Uani 1 1 d . . . . .
C11 C 0.4943(3) 0.38123(11) 0.3510(4) 0.0214(6) Uani 1 1 d . . . . .
O3 O 0.39847(19) 0.41350(8) 0.2933(3) 0.0260(4) Uani 1 1 d . . . . .
O4 O 0.51711(19) 0.34333(8) 0.2430(2) 0.0243(4) Uani 1 1 d . . . . .
C12 C 0.4257(3) 0.34403(13) 0.0526(4) 0.0290(7) Uani 1 1 d . . . . .
H12A H 0.333858 0.335997 0.047424 0.043 Uiso 1 1 calc R U . . .
H12B H 0.453707 0.316183 -0.017834 0.043 Uiso 1 1 calc R U . . .
H12C H 0.427665 0.380402 -0.000791 0.043 Uiso 1 1 calc R U . . .
C13 C 0.9531(3) 0.35316(11) 0.6424(3) 0.0213(6) Uani 1 1 d . . . . .
C14 C 1.0566(3) 0.38961(12) 0.6459(4) 0.0238(6) Uani 1 1 d . . . . .
H14 H 1.047658 0.427661 0.666590 0.029 Uiso 1 1 calc R U . . .
C15 C 1.1718(3) 0.37070(12) 0.6196(4) 0.0244(6) Uani 1 1 d . . . . .
H15 H 1.241823 0.395564 0.623515 0.029 Uiso 1 1 calc R U . . .
C16 C 1.1839(3) 0.31569(13) 0.5879(4) 0.0288(7) Uani 1 1 d . . . . .
Cl1 Cl 1.32885(8) 0.29241(3) 0.55195(13) 0.0451(3) Uani 1 1 d . . . . .
C17 C 1.0843(3) 0.27862(12) 0.5850(4) 0.0305(7) Uani 1 1 d . . . . .
H17 H 1.094437 0.240688 0.563937 0.037 Uiso 1 1 calc R U . . .
C18 C 0.9697(3) 0.29718(12) 0.6131(4) 0.0259(6) Uani 1 1 d . . . . .
H18 H 0.901606 0.271733 0.612547 0.031 Uiso 1 1 calc R U . . .
C19 C 0.0866(3) 0.41175(15) 0.1138(4) 0.0418(8) Uani 1 1 d . . . . .
H19A H 0.150049 0.409580 0.047948 0.063 Uiso 1 1 calc R U . . .
H19B H -0.005977 0.413497 0.024062 0.063 Uiso 1 1 calc R U . . .
H19C H 0.096677 0.379139 0.191862 0.063 Uiso 1 1 calc R U . . .
C20 C 0.1147(3) 0.46062(13) 0.2284(4) 0.0292(7) Uani 1 1 d . . . . .
N3 N 0.1392(3) 0.49858(12) 0.3203(4) 0.0423(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.400(4) . ?
C1 C2 1.405(4) . ?
C1 N1 1.415(3) . ?
C2 C3 1.395(4) . ?
C2 C7 1.467(4) . ?
C3 C4 1.378(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.344(3) . ?
C7 C8 1.366(4) . ?
O1 H1 0.90(3) . ?
C8 C11 1.463(4) . ?
C8 C9 1.508(4) . ?
C9 N2 1.461(3) . ?
C9 C10 1.530(4) . ?
C9 H9 1.0000 . ?
N2 C13 1.394(4) . ?
N2 H2N 0.92(3) . ?
C10 O2 1.230(3) . ?
C10 N1 1.359(3) . ?
N1 H1N 0.84(3) . ?
C11 O3 1.234(3) . ?
C11 O4 1.324(3) . ?
O4 C12 1.446(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.402(4) . ?
C13 C14 1.404(4) . ?
C14 C15 1.386(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(4) . ?
C16 Cl1 1.751(3) . ?
C17 C18 1.384(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.450(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 N3 1.138(4) . ?

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
C6 C1 C2 118.9(2) . . ?
C6 C1 N1 116.5(2) . . ?
C2 C1 N1 124.4(2) . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 C7 117.4(2) . . ?
C1 C2 C7 123.5(2) . . ?
C4 C3 C2 121.6(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 119.2(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 120.8(3) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O1 C7 C8 122.6(2) . . ?
O1 C7 C2 112.0(2) . . ?
C8 C7 C2 125.4(2) . . ?
C7 O1 H1 110(2) . . ?
C7 C8 C11 118.1(2) . . ?
C7 C8 C9 122.2(2) . . ?
C11 C8 C9 119.7(2) . . ?
N2 C9 C8 112.2(2) . . ?
N2 C9 C10 111.2(2) . . ?
C8 C9 C10 109.9(2) . . ?
N2 C9 H9 107.8 . . ?
C8 C9 H9 107.8 . . ?
C10 C9 H9 107.8 . . ?
C13 N2 C9 120.3(2) . . ?
C13 N2 H2N 116(2) . . ?
C9 N2 H2N 114(2) . . ?
O2 C10 N1 120.6(2) . . ?
O2 C10 C9 121.5(2) . . ?
N1 C10 C9 118.0(2) . . ?
C10 N1 C1 129.3(2) . . ?
C10 N1 H1N 118(2) . . ?
C1 N1 H1N 113(2) . . ?
O3 C11 O4 121.8(2) . . ?
O3 C11 C8 123.4(2) . . ?
O4 C11 C8 114.8(2) . . ?
C11 O4 C12 115.4(2) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C18 122.3(2) . . ?
N2 C13 C14 119.4(2) . . ?
C18 C13 C14 118.3(3) . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 119.5(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 121.2(3) . . ?
C15 C16 Cl1 119.1(2) . . ?
C17 C16 Cl1 119.7(2) . . ?
C16 C17 C18 119.5(3) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C13 120.7(3) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C20 C19 178.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.3(4) . . . . ?
N1 C1 C2 C3 173.8(2) . . . . ?
C6 C1 C2 C7 -176.7(3) . . . . ?
N1 C1 C2 C7 -2.6(4) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C7 C2 C3 C4 177.2(3) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
C4 C5 C6 C1 1.4(4) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
N1 C1 C6 C5 -175.2(3) . . . . ?
C3 C2 C7 O1 -29.7(3) . . . . ?
C1 C2 C7 O1 146.8(3) . . . . ?
C3 C2 C7 C8 149.6(3) . . . . ?
C1 C2 C7 C8 -33.9(4) . . . . ?
O1 C7 C8 C11 -3.7(4) . . . . ?
C2 C7 C8 C11 177.1(2) . . . . ?
O1 C7 C8 C9 177.0(2) . . . . ?
C2 C7 C8 C9 -2.3(4) . . . . ?
C7 C8 C9 N2 -59.9(3) . . . . ?
C11 C8 C9 N2 120.7(3) . . . . ?
C7 C8 C9 C10 64.3(3) . . . . ?
C11 C8 C9 C10 -115.1(3) . . . . ?
C8 C9 N2 C13 -148.8(2) . . . . ?
C10 C9 N2 C13 87.7(3) . . . . ?
N2 C9 C10 O2 -118.9(3) . . . . ?
C8 C9 C10 O2 116.2(3) . . . . ?
N2 C9 C10 N1 60.8(3) . . . . ?
C8 C9 C10 N1 -64.0(3) . . . . ?
O2 C10 N1 C1 -178.7(2) . . . . ?
C9 C10 N1 C1 1.5(4) . . . . ?
C6 C1 N1 C10 -147.4(3) . . . . ?
C2 C1 N1 C10 38.3(4) . . . . ?
C7 C8 C11 O3 5.7(4) . . . . ?
C9 C8 C11 O3 -174.9(2) . . . . ?
C7 C8 C11 O4 -173.7(2) . . . . ?
C9 C8 C11 O4 5.7(3) . . . . ?
O3 C11 O4 C12 2.4(4) . . . . ?
C8 C11 O4 C12 -178.2(2) . . . . ?
C9 N2 C13 C18 -24.2(4) . . . . ?
C9 N2 C13 C14 155.9(2) . . . . ?
N2 C13 C14 C15 -179.6(2) . . . . ?
C18 C13 C14 C15 0.5(4) . . . . ?
C13 C14 C15 C16 0.6(4) . . . . ?
C14 C15 C16 C17 -1.2(4) . . . . ?
C14 C15 C16 Cl1 179.2(2) . . . . ?
C15 C16 C17 C18 0.5(5) . . . . ?
Cl1 C16 C17 C18 -179.8(2) . . . . ?
C16 C17 C18 C13 0.7(5) . . . . ?
N2 C13 C18 C17 178.9(3) . . . . ?
C14 C13 C18 C17 -1.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O3 0.90(3) 1.73(4) 2.522(3) 145(3) . yes
C9 H9 O4 1.00 2.26 2.771(3) 110 . yes
N2 H2N N3 0.92(3) 2.23(4) 3.121(4) 165(3) 3_666 yes
N1 H1N O2 0.84(3) 2.08(3) 2.909(3) 170(3) 4_566 yes

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_dbt9
_database_code_depnum_ccdc_archive 'CCDC 2361040'
loop_
_audit_author_name
_audit_author_address
'Robert Gyepes'
;Department of Inorganic Chemistry, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2024-06-06 deposited with the CCDC.	2024-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 N O4 S'
_chemical_formula_sum            'C18 H15 N O4 S'
_chemical_formula_weight         341.37

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      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                   11.1923(5)
_cell_length_b                   14.2470(6)
_cell_length_c                   20.8183(9)
_cell_angle_alpha                99.961(3)
_cell_angle_beta                 97.508(3)
_cell_angle_gamma                100.781(3)
_cell_volume                     3165.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9854
_cell_measurement_theta_min      3.5153
_cell_measurement_theta_max      68.4215

_exptl_crystal_description       bar
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.039
_exptl_absorpt_coefficient_mu    2.018
_shelx_estimated_absorpt_T_min   0.539
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6175
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Kappa goniometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34489
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.186
_diffrn_reflns_theta_max         68.541
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             11553
_reflns_number_gt                8511
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0553P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_number_reflns         11553
_refine_ls_number_parameters     897
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1252
_refine_ls_wR_factor_gt          0.1145
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8835(2) 0.84344(17) -0.02752(11) 0.0181(5) Uani 1 1 d . . . . .
C2 C 0.8731(2) 0.74492(17) -0.02273(12) 0.0206(5) Uani 1 1 d . . . . .
C3 C 0.9530(2) 0.69297(17) -0.05236(12) 0.0231(5) Uani 1 1 d . . . . .
H3 H 0.948141 0.626843 -0.048749 0.028 Uiso 1 1 calc R U . . .
C4 C 1.0381(2) 0.73510(19) -0.08644(12) 0.0242(5) Uani 1 1 d . . . . .
H4 H 1.092274 0.698618 -0.105383 0.029 Uiso 1 1 calc R U . . .
C5 C 1.0451(2) 0.83150(19) -0.09325(12) 0.0245(5) Uani 1 1 d . . . . .
H5 H 1.102300 0.860403 -0.117872 0.029 Uiso 1 1 calc R U . . .
C6 C 0.9680(2) 0.88491(18) -0.06385(12) 0.0230(5) Uani 1 1 d . . . . .
H6 H 0.972668 0.950607 -0.068498 0.028 Uiso 1 1 calc R U . . .
C7 C 0.7796(2) 0.69270(17) 0.00925(12) 0.0223(5) Uani 1 1 d . . . . .
O1 O 0.74172(19) 0.59872(12) -0.02066(9) 0.0279(4) Uani 1 1 d . . . . .
H1 H 0.682(3) 0.570(3) 0.0012(17) 0.042 Uiso 1 1 d . U . . .
C8 C 0.7396(2) 0.73160(17) 0.06554(12) 0.0206(5) Uani 1 1 d . . . . .
C9 C 0.7814(2) 0.83774(17) 0.09936(12) 0.0214(5) Uani 1 1 d . . . . .
H9 H 0.732544 0.849011 0.135820 0.026 Uiso 1 1 calc R U . . .
S1 S 0.94382(6) 0.86426(4) 0.13751(3) 0.02411(15) Uani 1 1 d . . . . .
C10 C 0.7571(2) 0.90704(16) 0.05360(12) 0.0192(5) Uani 1 1 d . . . . .
N1 N 0.8064(2) 0.90306(15) -0.00231(10) 0.0201(4) Uani 1 1 d . . . . .
H1N H 0.792(3) 0.945(2) -0.0242(15) 0.027(8) Uiso 1 1 d . . . . .
O2 O 0.69405(17) 0.96759(12) 0.06848(9) 0.0237(4) Uani 1 1 d . . . . .
C11 C 0.6595(3) 0.66537(18) 0.09563(13) 0.0246(6) Uani 1 1 d . . . . .
O3 O 0.60672(19) 0.58169(13) 0.06787(10) 0.0334(5) Uani 1 1 d . . . . .
O4 O 0.65212(18) 0.70102(13) 0.15841(9) 0.0291(4) Uani 1 1 d . . . . .
C12 C 0.5778(3) 0.6341(2) 0.19041(16) 0.0434(8) Uani 1 1 d . . . . .
H12A H 0.491403 0.620108 0.168809 0.065 Uiso 1 1 calc R U . . .
H12B H 0.584372 0.663736 0.237203 0.065 Uiso 1 1 calc R U . . .
H12C H 0.607547 0.573192 0.186782 0.065 Uiso 1 1 calc R U . . .
C13 C 0.9661(3) 0.97950(18) 0.19151(12) 0.0241(6) Uani 1 1 d . . . . .
C14 C 1.0861(3) 1.03418(19) 0.20802(13) 0.0260(6) Uani 1 1 d . . . . .
H14 H 1.150107 1.011395 0.188425 0.031 Uiso 1 1 calc R U . . .
C15 C 1.1126(3) 1.1226(2) 0.25339(14) 0.0323(6) Uani 1 1 d . . . . .
H15 H 1.195170 1.159253 0.265184 0.039 Uiso 1 1 calc R U . . .
C16 C 1.0203(3) 1.1573(2) 0.28135(14) 0.0374(7) Uani 1 1 d . . . . .
H16 H 1.038983 1.217611 0.312307 0.045 Uiso 1 1 calc R U . . .
C17 C 0.9006(3) 1.1040(2) 0.26404(15) 0.0391(7) Uani 1 1 d . . . . .
H17 H 0.836686 1.128430 0.282720 0.047 Uiso 1 1 calc R U . . .
C18 C 0.8719(3) 1.0146(2) 0.21950(14) 0.0319(6) Uani 1 1 d . . . . .
H18 H 0.789293 0.977871 0.208299 0.038 Uiso 1 1 calc R U . . .
C21 C 0.0225(2) 0.33678(17) 0.47002(12) 0.0190(5) Uani 1 1 d . . . . .
C22 C -0.0102(2) 0.23740(17) 0.47298(12) 0.0213(5) Uani 1 1 d . . . . .
C23 C -0.1272(2) 0.18396(17) 0.44095(12) 0.0227(5) Uani 1 1 d . . . . .
H23 H -0.150362 0.116728 0.442161 0.027 Uiso 1 1 calc R U . . .
C24 C -0.2097(2) 0.22749(19) 0.40759(13) 0.0250(5) Uani 1 1 d . . . . .
H24 H -0.289194 0.190373 0.386814 0.030 Uiso 1 1 calc R U . . .
C25 C -0.1764(2) 0.32569(18) 0.40440(12) 0.0239(5) Uani 1 1 d . . . . .
H25 H -0.232735 0.355626 0.381306 0.029 Uiso 1 1 calc R U . . .
C26 C -0.0611(2) 0.37890(17) 0.43503(12) 0.0223(5) Uani 1 1 d . . . . .
H26 H -0.038094 0.445555 0.432295 0.027 Uiso 1 1 calc R U . . .
C27 C 0.0735(2) 0.18444(17) 0.50535(12) 0.0214(5) Uani 1 1 d . . . . .
O21 O 0.04987(18) 0.09004(12) 0.47503(9) 0.0270(4) Uani 1 1 d . . . . .
H21 H 0.103(3) 0.063(3) 0.4969(17) 0.041 Uiso 1 1 d . U . . .
C28 C 0.1603(2) 0.22249(17) 0.56054(12) 0.0211(5) Uani 1 1 d . . . . .
C29 C 0.1902(2) 0.32863(16) 0.59459(12) 0.0197(5) Uani 1 1 d . . . . .
H29 H 0.264621 0.338464 0.629349 0.024 Uiso 1 1 calc R U . . .
S21 S 0.06419(6) 0.35736(4) 0.63710(3) 0.02391(15) Uani 1 1 d . . . . .
C30 C 0.2217(2) 0.39934(16) 0.54940(12) 0.0202(5) Uani 1 1 d . . . . .
N21 N 0.1400(2) 0.39684(15) 0.49509(10) 0.0205(4) Uani 1 1 d . . . . .
H21N H 0.161(3) 0.441(2) 0.4756(14) 0.017(7) Uiso 1 1 d . . . . .
O22 O 0.32020(16) 0.46040(12) 0.56362(9) 0.0234(4) Uani 1 1 d . . . . .
C31 C 0.2233(2) 0.15513(18) 0.58990(13) 0.0231(5) Uani 1 1 d . . . . .
O23 O 0.21707(18) 0.06967(12) 0.56294(10) 0.0300(4) Uani 1 1 d . . . . .
O24 O 0.28739(18) 0.19224(13) 0.65060(10) 0.0298(4) Uani 1 1 d . . . . .
C32 C 0.3482(3) 0.1252(2) 0.68082(17) 0.0446(8) Uani 1 1 d . . . . .
H32A H 0.286244 0.068725 0.684539 0.067 Uiso 1 1 calc R U . . .
H32B H 0.392969 0.158371 0.724970 0.067 Uiso 1 1 calc R U . . .
H32C H 0.406307 0.103211 0.653326 0.067 Uiso 1 1 calc R U . . .
C33 C 0.1275(2) 0.47414(17) 0.68913(12) 0.0219(5) Uani 1 1 d . . . . .
C34 C 0.0423(3) 0.52814(19) 0.70893(13) 0.0252(6) Uani 1 1 d . . . . .
H34 H -0.043167 0.504289 0.692279 0.030 Uiso 1 1 calc R U . . .
C35 C 0.0831(3) 0.6174(2) 0.75332(13) 0.0305(6) Uani 1 1 d . . . . .
H35 H 0.025036 0.653886 0.767433 0.037 Uiso 1 1 calc R U . . .
C36 C 0.2075(3) 0.6529(2) 0.77682(14) 0.0323(6) Uani 1 1 d . . . . .
H36 H 0.234984 0.713446 0.807302 0.039 Uiso 1 1 calc R U . . .
C37 C 0.2920(3) 0.5998(2) 0.75577(14) 0.0319(6) Uani 1 1 d . . . . .
H37 H 0.377630 0.624852 0.771360 0.038 Uiso 1 1 calc R U . . .
C38 C 0.2528(3) 0.5106(2) 0.71220(13) 0.0278(6) Uani 1 1 d . . . . .
H38 H 0.311242 0.474439 0.698179 0.033 Uiso 1 1 calc R U . . .
C41 C 0.6153(2) 0.18607(17) 1.02448(12) 0.0201(5) Uani 1 1 d . . . . .
C42 C 0.6429(2) 0.28650(17) 1.02404(12) 0.0204(5) Uani 1 1 d . . . . .
C43 C 0.5750(3) 0.34653(18) 1.05837(12) 0.0251(6) Uani 1 1 d . . . . .
H43 H 0.591449 0.414386 1.058290 0.030 Uiso 1 1 calc R U . . .
C44 C 0.4852(3) 0.30875(19) 1.09202(13) 0.0261(6) Uani 1 1 d . . . . .
H44 H 0.439260 0.350202 1.113934 0.031 Uiso 1 1 calc R U . . .
C45 C 0.4618(3) 0.20996(19) 1.09387(13) 0.0264(6) Uani 1 1 d . . . . .
H45 H 0.402062 0.184195 1.118307 0.032 Uiso 1 1 calc R U . . .
C46 C 0.5260(2) 0.14948(18) 1.06000(12) 0.0245(5) Uani 1 1 d . . . . .
H46 H 0.508999 0.081886 1.060886 0.029 Uiso 1 1 calc R U . . .
C47 C 0.7424(2) 0.33475(17) 0.99369(12) 0.0218(5) Uani 1 1 d . . . . .
O41 O 0.79228(19) 0.42541(12) 1.02718(9) 0.0270(4) Uani 1 1 d . . . . .
H41 H 0.850(3) 0.449(3) 1.0069(17) 0.041 Uiso 1 1 d . U . . .
C48 C 0.7814(2) 0.29470(17) 0.93710(12) 0.0210(5) Uani 1 1 d . . . . .
C49 C 0.7262(2) 0.19261(17) 0.89946(12) 0.0210(5) Uani 1 1 d . . . . .
H49 H 0.776534 0.178909 0.864014 0.025 Uiso 1 1 calc R U . . .
S41 S 0.56801(6) 0.18235(4) 0.85744(3) 0.02468(15) Uani 1 1 d . . . . .
C50 C 0.7293(2) 0.11367(17) 0.93985(12) 0.0204(5) Uani 1 1 d . . . . .
N41 N 0.6789(2) 0.11841(14) 0.99535(10) 0.0198(4) Uani 1 1 d . . . . .
H41N H 0.680(3) 0.069(3) 1.0153(17) 0.040(9) Uiso 1 1 d . . . . .
O42 O 0.77653(17) 0.04416(12) 0.92042(9) 0.0249(4) Uani 1 1 d . . . . .
C51 C 0.8765(2) 0.35536(17) 0.91194(12) 0.0227(5) Uani 1 1 d . . . . .
O43 O 0.92975(18) 0.43898(13) 0.93979(10) 0.0300(4) Uani 1 1 d . . . . .
O44 O 0.90323(18) 0.31376(12) 0.85417(9) 0.0284(4) Uani 1 1 d . . . . .
C52 C 1.0030(3) 0.3708(2) 0.83017(15) 0.0361(7) Uani 1 1 d . . . . .
H52A H 0.980684 0.431520 0.821999 0.054 Uiso 1 1 calc R U . . .
H52B H 1.017513 0.333250 0.788907 0.054 Uiso 1 1 calc R U . . .
H52C H 1.078152 0.386132 0.863370 0.054 Uiso 1 1 calc R U . . .
C53 C 0.5510(2) 0.07068(18) 0.79968(12) 0.0233(5) Uani 1 1 d . . . . .
C54 C 0.6176(3) 0.0676(2) 0.74706(13) 0.0279(6) Uani 1 1 d . . . . .
H54 H 0.671719 0.124897 0.742207 0.033 Uiso 1 1 calc R U . . .
C55 C 0.6043(3) -0.0187(2) 0.70245(14) 0.0326(6) Uani 1 1 d . . . . .
H55 H 0.650128 -0.020722 0.667078 0.039 Uiso 1 1 calc R U . . .
C56 C 0.5249(3) -0.1025(2) 0.70863(14) 0.0324(6) Uani 1 1 d . . . . .
H56 H 0.516604 -0.161847 0.677825 0.039 Uiso 1 1 calc R U . . .
C57 C 0.4576(3) -0.0992(2) 0.76008(14) 0.0330(6) Uani 1 1 d . . . . .
H57 H 0.402258 -0.156376 0.764115 0.040 Uiso 1 1 calc R U . . .
C58 C 0.4705(3) -0.0127(2) 0.80585(13) 0.0283(6) Uani 1 1 d . . . . .
H58 H 0.424382 -0.010867 0.841098 0.034 Uiso 1 1 calc R U . . .
C61 C 0.4743(2) 0.68224(18) 0.51908(12) 0.0231(5) Uani 1 1 d . . . . .
H61N H 0.348(3) 0.567(2) 0.5115(15) 0.029(8) Uiso 1 1 d . . . . .
C62 C 0.5642(3) 0.6466(2) 0.55506(13) 0.0276(6) Uani 1 1 d . . . . .
H62 H 0.548835 0.579662 0.557772 0.033 Uiso 1 1 calc R U . . .
C63 C 0.6752(3) 0.7074(2) 0.58674(13) 0.0314(6) Uani 1 1 d . . . . .
H63 H 0.735095 0.682577 0.611595 0.038 Uiso 1 1 calc R U . . .
C64 C 0.6986(3) 0.8055(2) 0.58190(13) 0.0334(7) Uani 1 1 d . . . . .
H64 H 0.775726 0.847363 0.601994 0.040 Uiso 1 1 calc R U . . .
C65 C 0.6091(3) 0.8413(2) 0.54784(13) 0.0309(6) Uani 1 1 d . . . . .
H65 H 0.625398 0.908292 0.545300 0.037 Uiso 1 1 calc R U . . .
C66 C 0.4947(3) 0.78166(18) 0.51677(12) 0.0252(6) Uani 1 1 d . . . . .
C67 C 0.4005(3) 0.82883(17) 0.48815(13) 0.0260(6) Uani 1 1 d . . . . .
O61 O 0.4099(2) 0.91964(13) 0.52297(9) 0.0341(5) Uani 1 1 d . . . . .
H61 H 0.351(3) 0.945(3) 0.5021(19) 0.051 Uiso 1 1 d . U . . .
C68 C 0.3154(3) 0.78915(17) 0.43217(13) 0.0245(6) Uani 1 1 d . . . . .
C69 C 0.3040(2) 0.68696(17) 0.39435(12) 0.0216(5) Uani 1 1 d . . . . .
H69 H 0.229345 0.672892 0.359226 0.026 Uiso 1 1 calc R U . . .
S61 S 0.43652(6) 0.67771(5) 0.35151(3) 0.02707(16) Uani 1 1 d . . . . .
C70 C 0.2841(2) 0.60889(17) 0.43527(12) 0.0214(5) Uani 1 1 d . . . . .
N61 N 0.3647(2) 0.61392(15) 0.49076(10) 0.0211(4) Uani 1 1 d . . . . .
O62 O 0.19534(17) 0.53888(12) 0.41678(9) 0.0250(4) Uani 1 1 d . . . . .
C71 C 0.2357(3) 0.84976(18) 0.40799(13) 0.0263(6) Uani 1 1 d . . . . .
O63 O 0.2323(2) 0.93180(13) 0.43779(10) 0.0369(5) Uani 1 1 d . . . . .
O64 O 0.16619(18) 0.81097(13) 0.34853(9) 0.0294(4) Uani 1 1 d . . . . .
C72 C 0.0825(3) 0.8689(2) 0.32445(16) 0.0383(7) Uani 1 1 d . . . . .
H72A H 0.025726 0.879420 0.355719 0.057 Uiso 1 1 calc R U . . .
H72B H 0.035287 0.834184 0.281130 0.057 Uiso 1 1 calc R U . . .
H72C H 0.130186 0.931984 0.320279 0.057 Uiso 1 1 calc R U . . .
C73 C 0.3756(2) 0.56353(19) 0.29575(13) 0.0250(6) Uani 1 1 d . . . . .
C74 C 0.2876(3) 0.5574(2) 0.24008(13) 0.0297(6) Uani 1 1 d . . . . .
H74 H 0.261335 0.614354 0.231502 0.036 Uiso 1 1 calc R U . . .
C75 C 0.2388(3) 0.4688(2) 0.19761(14) 0.0356(7) Uani 1 1 d . . . . .
H75 H 0.178732 0.464871 0.159927 0.043 Uiso 1 1 calc R U . . .
C76 C 0.2773(3) 0.3855(2) 0.20986(15) 0.0352(7) Uani 1 1 d . . . . .
H76 H 0.243258 0.324397 0.180740 0.042 Uiso 1 1 calc R U . . .
C77 C 0.3651(3) 0.3915(2) 0.26448(15) 0.0355(7) Uani 1 1 d . . . . .
H77 H 0.391128 0.334379 0.272889 0.043 Uiso 1 1 calc R U . . .
C78 C 0.4160(3) 0.4810(2) 0.30742(14) 0.0310(6) Uani 1 1 d . . . . .
H78 H 0.477762 0.485250 0.344344 0.037 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
C1 C6 1.395(4) . ?
C1 N1 1.407(3) . ?
C1 C2 1.408(3) . ?
C2 C3 1.401(4) . ?
C2 C7 1.468(4) . ?
C3 C4 1.372(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.338(3) . ?
C7 C8 1.374(4) . ?
O1 H1 0.93(3) . ?
C8 C11 1.456(4) . ?
C8 C9 1.511(3) . ?
C9 C10 1.521(3) . ?
C9 S1 1.828(3) . ?
C9 H9 1.0000 . ?
S1 C13 1.777(2) . ?
C10 O2 1.237(3) . ?
C10 N1 1.349(3) . ?
N1 H1N 0.84(3) . ?
C11 O3 1.230(3) . ?
C11 O4 1.337(3) . ?
O4 C12 1.454(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.387(4) . ?
C13 C18 1.399(4) . ?
C14 C15 1.393(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.395(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C21 C26 1.396(4) . ?
C21 N21 1.407(3) . ?
C21 C22 1.409(3) . ?
C22 C23 1.401(4) . ?
C22 C27 1.475(4) . ?
C23 C24 1.383(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.394(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.378(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 O21 1.344(3) . ?
C27 C28 1.362(4) . ?
O21 H21 0.89(4) . ?
C28 C31 1.461(3) . ?
C28 C29 1.510(3) . ?
C29 C30 1.518(3) . ?
C29 S21 1.832(3) . ?
C29 H29 1.0000 . ?
S21 C33 1.783(2) . ?
C30 O22 1.236(3) . ?
C30 N21 1.349(3) . ?
N21 H21N 0.82(3) . ?
C31 O23 1.235(3) . ?
C31 O24 1.335(3) . ?
O24 C32 1.453(3) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C38 1.389(4) . ?
C33 C34 1.392(4) . ?
C34 C35 1.395(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.380(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.385(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.386(4) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C41 C46 1.397(4) . ?
C41 N41 1.404(3) . ?
C41 C42 1.408(3) . ?
C42 C43 1.412(3) . ?
C42 C47 1.470(4) . ?
C43 C44 1.379(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.391(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.381(4) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 O41 1.335(3) . ?
C47 C48 1.378(4) . ?
O41 H41 0.86(3) . ?
C48 C51 1.454(4) . ?
C48 C49 1.501(3) . ?
C49 C50 1.519(3) . ?
C49 S41 1.837(3) . ?
C49 H49 1.0000 . ?
S41 C53 1.783(2) . ?
C50 O42 1.240(3) . ?
C50 N41 1.347(3) . ?
N41 H41N 0.88(4) . ?
C51 O43 1.231(3) . ?
C51 O44 1.342(3) . ?
O44 C52 1.450(3) . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 C58 1.387(4) . ?
C53 C54 1.403(4) . ?
C54 C55 1.377(4) . ?
C54 H54 0.9500 . ?
C55 C56 1.385(4) . ?
C55 H55 0.9500 . ?
C56 C57 1.387(4) . ?
C56 H56 0.9500 . ?
C57 C58 1.392(4) . ?
C57 H57 0.9500 . ?
C58 H58 0.9500 . ?
C61 C62 1.399(4) . ?
C61 C66 1.402(4) . ?
C61 N61 1.403(3) . ?
C62 C63 1.383(4) . ?
C62 H62 0.9500 . ?
C63 C64 1.398(4) . ?
C63 H63 0.9500 . ?
C64 C65 1.376(4) . ?
C64 H64 0.9500 . ?
C65 C66 1.402(4) . ?
C65 H65 0.9500 . ?
C66 C67 1.469(4) . ?
C67 O61 1.347(3) . ?
C67 C68 1.366(4) . ?
O61 H61 0.91(4) . ?
C68 C71 1.455(4) . ?
C68 C69 1.505(3) . ?
C69 C70 1.516(3) . ?
C69 S61 1.841(3) . ?
C69 H69 1.0000 . ?
S61 C73 1.784(3) . ?
C70 O62 1.236(3) . ?
C70 N61 1.352(3) . ?
N61 H61N 0.86(3) . ?
C71 O63 1.235(3) . ?
C71 O64 1.339(3) . ?
O64 C72 1.455(3) . ?
C72 H72A 0.9800 . ?
C72 H72B 0.9800 . ?
C72 H72C 0.9800 . ?
C73 C78 1.383(4) . ?
C73 C74 1.398(4) . ?
C74 C75 1.379(4) . ?
C74 H74 0.9500 . ?
C75 C76 1.389(4) . ?
C75 H75 0.9500 . ?
C76 C77 1.382(4) . ?
C76 H76 0.9500 . ?
C77 C78 1.397(4) . ?
C77 H77 0.9500 . ?
C78 H78 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
C6 C1 N1 115.9(2) . . ?
C6 C1 C2 119.6(2) . . ?
N1 C1 C2 124.3(2) . . ?
C3 C2 C1 118.3(2) . . ?
C3 C2 C7 118.2(2) . . ?
C1 C2 C7 123.4(2) . . ?
C4 C3 C2 121.7(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 120.9(2) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O1 C7 C8 122.6(2) . . ?
O1 C7 C2 111.8(2) . . ?
C8 C7 C2 125.5(2) . . ?
C7 O1 H1 108(2) . . ?
C7 C8 C11 117.8(2) . . ?
C7 C8 C9 122.9(2) . . ?
C11 C8 C9 119.2(2) . . ?
C8 C9 C10 113.0(2) . . ?
C8 C9 S1 110.45(17) . . ?
C10 C9 S1 111.38(17) . . ?
C8 C9 H9 107.2 . . ?
C10 C9 H9 107.2 . . ?
S1 C9 H9 107.2 . . ?
C13 S1 C9 104.23(12) . . ?
O2 C10 N1 120.6(2) . . ?
O2 C10 C9 119.8(2) . . ?
N1 C10 C9 119.6(2) . . ?
C10 N1 C1 130.2(2) . . ?
C10 N1 H1N 115(2) . . ?
C1 N1 H1N 115(2) . . ?
O3 C11 O4 121.5(2) . . ?
O3 C11 C8 124.1(2) . . ?
O4 C11 C8 114.3(2) . . ?
C11 O4 C12 115.1(2) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 119.7(2) . . ?
C14 C13 S1 116.3(2) . . ?
C18 C13 S1 123.9(2) . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.7(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 119.5(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.9(3) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C13 119.3(3) . . ?
C17 C18 H18 120.4 . . ?
C13 C18 H18 120.4 . . ?
C26 C21 N21 115.7(2) . . ?
C26 C21 C22 119.6(2) . . ?
N21 C21 C22 124.4(2) . . ?
C23 C22 C21 118.5(2) . . ?
C23 C22 C27 117.5(2) . . ?
C21 C22 C27 124.0(2) . . ?
C24 C23 C22 121.1(2) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 120.2(2) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C26 C25 C24 119.4(2) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C25 C26 C21 121.3(2) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
O21 C27 C28 122.9(2) . . ?
O21 C27 C22 111.1(2) . . ?
C28 C27 C22 125.9(2) . . ?
C27 O21 H21 106(2) . . ?
C27 C28 C31 117.5(2) . . ?
C27 C28 C29 123.8(2) . . ?
C31 C28 C29 118.6(2) . . ?
C28 C29 C30 114.3(2) . . ?
C28 C29 S21 110.25(17) . . ?
C30 C29 S21 110.61(16) . . ?
C28 C29 H29 107.1 . . ?
C30 C29 H29 107.1 . . ?
S21 C29 H29 107.1 . . ?
C33 S21 C29 104.36(12) . . ?
O22 C30 N21 120.5(2) . . ?
O22 C30 C29 119.8(2) . . ?
N21 C30 C29 119.6(2) . . ?
C30 N21 C21 130.8(2) . . ?
C30 N21 H21N 113(2) . . ?
C21 N21 H21N 116(2) . . ?
O23 C31 O24 121.1(2) . . ?
O23 C31 C28 124.3(2) . . ?
O24 C31 C28 114.5(2) . . ?
C31 O24 C32 115.0(2) . . ?
O24 C32 H32A 109.5 . . ?
O24 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O24 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C38 C33 C34 119.9(2) . . ?
C38 C33 S21 124.3(2) . . ?
C34 C33 S21 115.8(2) . . ?
C33 C34 C35 119.7(3) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C36 C35 C34 120.3(3) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C35 C36 C37 119.7(3) . . ?
C35 C36 H36 120.1 . . ?
C37 C36 H36 120.1 . . ?
C36 C37 C38 120.6(3) . . ?
C36 C37 H37 119.7 . . ?
C38 C37 H37 119.7 . . ?
C37 C38 C33 119.7(3) . . ?
C37 C38 H38 120.2 . . ?
C33 C38 H38 120.2 . . ?
C46 C41 N41 115.6(2) . . ?
C46 C41 C42 119.8(2) . . ?
N41 C41 C42 124.3(2) . . ?
C41 C42 C43 117.9(2) . . ?
C41 C42 C47 124.7(2) . . ?
C43 C42 C47 117.2(2) . . ?
C44 C43 C42 121.4(2) . . ?
C44 C43 H43 119.3 . . ?
C42 C43 H43 119.3 . . ?
C43 C44 C45 120.0(2) . . ?
C43 C44 H44 120.0 . . ?
C45 C44 H44 120.0 . . ?
C46 C45 C44 119.7(3) . . ?
C46 C45 H45 120.2 . . ?
C44 C45 H45 120.2 . . ?
C45 C46 C41 121.1(2) . . ?
C45 C46 H46 119.5 . . ?
C41 C46 H46 119.5 . . ?
O41 C47 C48 122.3(2) . . ?
O41 C47 C42 111.9(2) . . ?
C48 C47 C42 125.8(2) . . ?
C47 O41 H41 107(2) . . ?
C47 C48 C51 118.3(2) . . ?
C47 C48 C49 122.5(2) . . ?
C51 C48 C49 119.1(2) . . ?
C48 C49 C50 115.1(2) . . ?
C48 C49 S41 111.29(17) . . ?
C50 C49 S41 109.99(18) . . ?
C48 C49 H49 106.7 . . ?
C50 C49 H49 106.7 . . ?
S41 C49 H49 106.7 . . ?
C53 S41 C49 99.12(12) . . ?
O42 C50 N41 120.6(2) . . ?
O42 C50 C49 119.2(2) . . ?
N41 C50 C49 120.2(2) . . ?
C50 N41 C41 130.6(2) . . ?
C50 N41 H41N 116(2) . . ?
C41 N41 H41N 114(2) . . ?
O43 C51 O44 120.9(2) . . ?
O43 C51 C48 124.3(2) . . ?
O44 C51 C48 114.8(2) . . ?
C51 O44 C52 115.7(2) . . ?
O44 C52 H52A 109.5 . . ?
O44 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
O44 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C58 C53 C54 119.9(2) . . ?
C58 C53 S41 120.3(2) . . ?
C54 C53 S41 119.8(2) . . ?
C55 C54 C53 119.8(3) . . ?
C55 C54 H54 120.1 . . ?
C53 C54 H54 120.1 . . ?
C54 C55 C56 120.7(3) . . ?
C54 C55 H55 119.7 . . ?
C56 C55 H55 119.7 . . ?
C55 C56 C57 119.6(3) . . ?
C55 C56 H56 120.2 . . ?
C57 C56 H56 120.2 . . ?
C56 C57 C58 120.5(3) . . ?
C56 C57 H57 119.8 . . ?
C58 C57 H57 119.8 . . ?
C53 C58 C57 119.6(3) . . ?
C53 C58 H58 120.2 . . ?
C57 C58 H58 120.2 . . ?
C62 C61 C66 119.8(2) . . ?
C62 C61 N61 115.5(2) . . ?
C66 C61 N61 124.6(2) . . ?
C63 C62 C61 121.0(3) . . ?
C63 C62 H62 119.5 . . ?
C61 C62 H62 119.5 . . ?
C62 C63 C64 119.4(3) . . ?
C62 C63 H63 120.3 . . ?
C64 C63 H63 120.3 . . ?
C65 C64 C63 119.6(3) . . ?
C65 C64 H64 120.2 . . ?
C63 C64 H64 120.2 . . ?
C64 C65 C66 121.9(3) . . ?
C64 C65 H65 119.0 . . ?
C66 C65 H65 119.0 . . ?
C65 C66 C61 118.1(3) . . ?
C65 C66 C67 117.7(2) . . ?
C61 C66 C67 124.1(2) . . ?
O61 C67 C68 122.8(3) . . ?
O61 C67 C66 111.5(2) . . ?
C68 C67 C66 125.7(2) . . ?
C67 O61 H61 107(2) . . ?
C67 C68 C71 118.0(2) . . ?
C67 C68 C69 122.4(2) . . ?
C71 C68 C69 119.5(2) . . ?
C68 C69 C70 114.5(2) . . ?
C68 C69 S61 111.18(18) . . ?
C70 C69 S61 110.63(18) . . ?
C68 C69 H69 106.7 . . ?
C70 C69 H69 106.7 . . ?
S61 C69 H69 106.7 . . ?
C73 S61 C69 99.48(12) . . ?
O62 C70 N61 119.8(2) . . ?
O62 C70 C69 119.7(2) . . ?
N61 C70 C69 120.5(2) . . ?
C70 N61 C61 130.1(2) . . ?
C70 N61 H61N 116(2) . . ?
C61 N61 H61N 114(2) . . ?
O63 C71 O64 121.0(3) . . ?
O63 C71 C68 124.3(2) . . ?
O64 C71 C68 114.7(2) . . ?
C71 O64 C72 115.6(2) . . ?
O64 C72 H72A 109.5 . . ?
O64 C72 H72B 109.5 . . ?
H72A C72 H72B 109.5 . . ?
O64 C72 H72C 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 109.5 . . ?
C78 C73 C74 119.9(3) . . ?
C78 C73 S61 119.9(2) . . ?
C74 C73 S61 120.1(2) . . ?
C75 C74 C73 120.2(3) . . ?
C75 C74 H74 119.9 . . ?
C73 C74 H74 119.9 . . ?
C74 C75 C76 120.1(3) . . ?
C74 C75 H75 120.0 . . ?
C76 C75 H75 120.0 . . ?
C77 C76 C75 119.9(3) . . ?
C77 C76 H76 120.1 . . ?
C75 C76 H76 120.1 . . ?
C76 C77 C78 120.5(3) . . ?
C76 C77 H77 119.8 . . ?
C78 C77 H77 119.8 . . ?
C73 C78 C77 119.5(3) . . ?
C73 C78 H78 120.3 . . ?
C77 C78 H78 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 3.0(4) . . . . ?
N1 C1 C2 C3 177.5(2) . . . . ?
C6 C1 C2 C7 -174.3(2) . . . . ?
N1 C1 C2 C7 0.2(4) . . . . ?
C1 C2 C3 C4 -1.3(4) . . . . ?
C7 C2 C3 C4 176.2(2) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C3 C4 C5 C6 1.8(4) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
N1 C1 C6 C5 -177.4(2) . . . . ?
C2 C1 C6 C5 -2.4(4) . . . . ?
C3 C2 C7 O1 -31.5(3) . . . . ?
C1 C2 C7 O1 145.8(2) . . . . ?
C3 C2 C7 C8 144.5(3) . . . . ?
C1 C2 C7 C8 -38.1(4) . . . . ?
O1 C7 C8 C11 4.4(4) . . . . ?
C2 C7 C8 C11 -171.3(2) . . . . ?
O1 C7 C8 C9 -179.7(2) . . . . ?
C2 C7 C8 C9 4.7(4) . . . . ?
C7 C8 C9 C10 56.0(3) . . . . ?
C11 C8 C9 C10 -128.0(2) . . . . ?
C7 C8 C9 S1 -69.5(3) . . . . ?
C11 C8 C9 S1 106.5(2) . . . . ?
C8 C9 S1 C13 -165.52(17) . . . . ?
C10 C9 S1 C13 68.05(19) . . . . ?
C8 C9 C10 O2 123.0(3) . . . . ?
S1 C9 C10 O2 -112.0(2) . . . . ?
C8 C9 C10 N1 -58.2(3) . . . . ?
S1 C9 C10 N1 66.8(3) . . . . ?
O2 C10 N1 C1 177.5(2) . . . . ?
C9 C10 N1 C1 -1.3(4) . . . . ?
C6 C1 N1 C10 -148.0(3) . . . . ?
C2 C1 N1 C10 37.3(4) . . . . ?
C7 C8 C11 O3 -14.5(4) . . . . ?
C9 C8 C11 O3 169.4(2) . . . . ?
C7 C8 C11 O4 162.2(2) . . . . ?
C9 C8 C11 O4 -13.9(3) . . . . ?
O3 C11 O4 C12 -0.1(4) . . . . ?
C8 C11 O4 C12 -176.9(2) . . . . ?
C9 S1 C13 C14 -156.7(2) . . . . ?
C9 S1 C13 C18 26.2(3) . . . . ?
C18 C13 C14 C15 1.4(4) . . . . ?
S1 C13 C14 C15 -175.9(2) . . . . ?
C13 C14 C15 C16 -1.1(4) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C15 C16 C17 C18 1.1(5) . . . . ?
C16 C17 C18 C13 -0.8(5) . . . . ?
C14 C13 C18 C17 -0.4(4) . . . . ?
S1 C13 C18 C17 176.7(2) . . . . ?
C26 C21 C22 C23 -0.7(4) . . . . ?
N21 C21 C22 C23 -174.5(2) . . . . ?
C26 C21 C22 C27 176.5(2) . . . . ?
N21 C21 C22 C27 2.7(4) . . . . ?
C21 C22 C23 C24 -0.6(4) . . . . ?
C27 C22 C23 C24 -177.9(2) . . . . ?
C22 C23 C24 C25 1.1(4) . . . . ?
C23 C24 C25 C26 -0.4(4) . . . . ?
C24 C25 C26 C21 -0.9(4) . . . . ?
N21 C21 C26 C25 175.7(2) . . . . ?
C22 C21 C26 C25 1.4(4) . . . . ?
C23 C22 C27 O21 28.6(3) . . . . ?
C21 C22 C27 O21 -148.6(2) . . . . ?
C23 C22 C27 C28 -148.5(3) . . . . ?
C21 C22 C27 C28 34.3(4) . . . . ?
O21 C27 C28 C31 -4.4(4) . . . . ?
C22 C27 C28 C31 172.3(2) . . . . ?
O21 C27 C28 C29 178.7(2) . . . . ?
C22 C27 C28 C29 -4.6(4) . . . . ?
C27 C28 C29 C30 -53.6(3) . . . . ?
C31 C28 C29 C30 129.6(2) . . . . ?
C27 C28 C29 S21 71.7(3) . . . . ?
C31 C28 C29 S21 -105.1(2) . . . . ?
C28 C29 S21 C33 167.15(17) . . . . ?
C30 C29 S21 C33 -65.47(19) . . . . ?
C28 C29 C30 O22 -125.1(2) . . . . ?
S21 C29 C30 O22 109.8(2) . . . . ?
C28 C29 C30 N21 56.9(3) . . . . ?
S21 C29 C30 N21 -68.2(2) . . . . ?
O22 C30 N21 C21 -178.2(2) . . . . ?
C29 C30 N21 C21 -0.2(4) . . . . ?
C26 C21 N21 C30 149.6(2) . . . . ?
C22 C21 N21 C30 -36.4(4) . . . . ?
C27 C28 C31 O23 11.5(4) . . . . ?
C29 C28 C31 O23 -171.4(2) . . . . ?
C27 C28 C31 O24 -166.7(2) . . . . ?
C29 C28 C31 O24 10.4(3) . . . . ?
O23 C31 O24 C32 0.5(4) . . . . ?
C28 C31 O24 C32 178.7(2) . . . . ?
C29 S21 C33 C38 -24.7(2) . . . . ?
C29 S21 C33 C34 158.10(19) . . . . ?
C38 C33 C34 C35 -1.8(4) . . . . ?
S21 C33 C34 C35 175.6(2) . . . . ?
C33 C34 C35 C36 1.0(4) . . . . ?
C34 C35 C36 C37 0.5(4) . . . . ?
C35 C36 C37 C38 -1.1(4) . . . . ?
C36 C37 C38 C33 0.3(4) . . . . ?
C34 C33 C38 C37 1.1(4) . . . . ?
S21 C33 C38 C37 -176.0(2) . . . . ?
C46 C41 C42 C43 -2.1(4) . . . . ?
N41 C41 C42 C43 -176.8(2) . . . . ?
C46 C41 C42 C47 174.2(2) . . . . ?
N41 C41 C42 C47 -0.6(4) . . . . ?
C41 C42 C43 C44 0.7(4) . . . . ?
C47 C42 C43 C44 -175.8(2) . . . . ?
C42 C43 C44 C45 1.4(4) . . . . ?
C43 C44 C45 C46 -2.2(4) . . . . ?
C44 C45 C46 C41 0.8(4) . . . . ?
N41 C41 C46 C45 176.5(2) . . . . ?
C42 C41 C46 C45 1.3(4) . . . . ?
C41 C42 C47 O41 -146.3(2) . . . . ?
C43 C42 C47 O41 29.9(3) . . . . ?
C41 C42 C47 C48 34.6(4) . . . . ?
C43 C42 C47 C48 -149.1(3) . . . . ?
O41 C47 C48 C51 -2.6(4) . . . . ?
C42 C47 C48 C51 176.4(2) . . . . ?
O41 C47 C48 C49 179.6(2) . . . . ?
C42 C47 C48 C49 -1.4(4) . . . . ?
C47 C48 C49 C50 -55.6(3) . . . . ?
C51 C48 C49 C50 126.7(2) . . . . ?
C47 C48 C49 S41 70.4(3) . . . . ?
C51 C48 C49 S41 -107.3(2) . . . . ?
C48 C49 S41 C53 162.58(18) . . . . ?
C50 C49 S41 C53 -68.71(18) . . . . ?
C48 C49 C50 O42 -125.8(3) . . . . ?
S41 C49 C50 O42 107.6(2) . . . . ?
C48 C49 C50 N41 55.5(3) . . . . ?
S41 C49 C50 N41 -71.1(3) . . . . ?
O42 C50 N41 C41 -176.1(2) . . . . ?
C49 C50 N41 C41 2.5(4) . . . . ?
C46 C41 N41 C50 149.7(3) . . . . ?
C42 C41 N41 C50 -35.4(4) . . . . ?
C47 C48 C51 O43 4.0(4) . . . . ?
C49 C48 C51 O43 -178.1(2) . . . . ?
C47 C48 C51 O44 -175.4(2) . . . . ?
C49 C48 C51 O44 2.5(3) . . . . ?
O43 C51 O44 C52 4.1(4) . . . . ?
C48 C51 O44 C52 -176.5(2) . . . . ?
C49 S41 C53 C58 111.2(2) . . . . ?
C49 S41 C53 C54 -70.0(2) . . . . ?
C58 C53 C54 C55 -1.1(4) . . . . ?
S41 C53 C54 C55 -180.0(2) . . . . ?
C53 C54 C55 C56 0.6(4) . . . . ?
C54 C55 C56 C57 0.4(5) . . . . ?
C55 C56 C57 C58 -0.8(5) . . . . ?
C54 C53 C58 C57 0.7(4) . . . . ?
S41 C53 C58 C57 179.6(2) . . . . ?
C56 C57 C58 C53 0.2(4) . . . . ?
C66 C61 C62 C63 -2.2(4) . . . . ?
N61 C61 C62 C63 -178.4(2) . . . . ?
C61 C62 C63 C64 -1.0(4) . . . . ?
C62 C63 C64 C65 2.5(4) . . . . ?
C63 C64 C65 C66 -0.8(4) . . . . ?
C64 C65 C66 C61 -2.3(4) . . . . ?
C64 C65 C66 C67 173.3(2) . . . . ?
C62 C61 C66 C65 3.8(4) . . . . ?
N61 C61 C66 C65 179.6(2) . . . . ?
C62 C61 C66 C67 -171.5(2) . . . . ?
N61 C61 C66 C67 4.3(4) . . . . ?
C65 C66 C67 O61 -32.3(3) . . . . ?
C61 C66 C67 O61 143.0(2) . . . . ?
C65 C66 C67 C68 145.7(3) . . . . ?
C61 C66 C67 C68 -39.0(4) . . . . ?
O61 C67 C68 C71 2.8(4) . . . . ?
C66 C67 C68 C71 -174.9(2) . . . . ?
O61 C67 C68 C69 -178.8(2) . . . . ?
C66 C67 C68 C69 3.5(4) . . . . ?
C67 C68 C69 C70 55.5(3) . . . . ?
C71 C68 C69 C70 -126.1(3) . . . . ?
C67 C68 C69 S61 -70.8(3) . . . . ?
C71 C68 C69 S61 107.6(2) . . . . ?
C68 C69 S61 C73 -164.73(19) . . . . ?
C70 C69 S61 C73 66.9(2) . . . . ?
C68 C69 C70 O62 126.1(3) . . . . ?
S61 C69 C70 O62 -107.4(2) . . . . ?
C68 C69 C70 N61 -55.8(3) . . . . ?
S61 C69 C70 N61 70.7(3) . . . . ?
O62 C70 N61 C61 176.0(2) . . . . ?
C69 C70 N61 C61 -2.1(4) . . . . ?
C62 C61 N61 C70 -150.4(3) . . . . ?
C66 C61 N61 C70 33.6(4) . . . . ?
C67 C68 C71 O63 -6.7(4) . . . . ?
C69 C68 C71 O63 174.9(2) . . . . ?
C67 C68 C71 O64 171.5(2) . . . . ?
C69 C68 C71 O64 -6.9(3) . . . . ?
O63 C71 O64 C72 -3.8(4) . . . . ?
C68 C71 O64 C72 177.9(2) . . . . ?
C69 S61 C73 C78 -105.1(2) . . . . ?
C69 S61 C73 C74 75.3(2) . . . . ?
C78 C73 C74 C75 1.5(4) . . . . ?
S61 C73 C74 C75 -178.8(2) . . . . ?
C73 C74 C75 C76 -0.3(5) . . . . ?
C74 C75 C76 C77 -0.4(5) . . . . ?
C75 C76 C77 C78 -0.2(5) . . . . ?
C74 C73 C78 C77 -2.1(4) . . . . ?
S61 C73 C78 C77 178.2(2) . . . . ?
C76 C77 C78 C73 1.5(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O3 0.93(3) 1.71(4) 2.546(3) 148(3) . yes
N1 H1N O42 0.84(3) 1.99(3) 2.823(3) 174(3) 1_564 yes
C14 H14 O42 0.95 2.56 3.383(3) 145 2_766 yes
O21 H21 O23 0.89(4) 1.72(4) 2.535(3) 150(3) . yes
N21 H21N O62 0.82(3) 2.03(3) 2.841(3) 172(3) . yes
C34 H34 O62 0.95 2.56 3.347(3) 141 2_566 yes
O41 H41 O43 0.86(3) 1.75(3) 2.541(3) 151(3) . yes
C49 H49 O44 1.00 2.22 2.751(3) 112 . yes
N41 H41N O2 0.88(4) 1.98(4) 2.857(3) 174(3) 1_546 yes
C58 H58 O2 0.95 2.50 3.430(3) 167 2_666 yes
N61 H61N O22 0.86(3) 2.02(3) 2.876(3) 176(3) . yes
O61 H61 O63 0.91(4) 1.71(4) 2.538(3) 149(4) . yes
C69 H69 O64 1.00 2.25 2.762(3) 111 . yes

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.064

