# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2025

####################################################################### 
# 
# 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_mo_pg300124_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2380170'
_audit_update_record             
;
2024-08-27 deposited with the CCDC.	2025-05-05 downloaded from the CCDC.
;
_audit_creation_date             2024-02-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H6 O S, C9 H4 N2 O2 S'
_chemical_formula_sum            'C11 H10 N2 O3 S2'
_chemical_formula_weight         282.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6557(16)
_cell_length_b                   9.109(2)
_cell_length_c                   10.049(2)
_cell_angle_alpha                80.505(8)
_cell_angle_beta                 69.600(7)
_cell_angle_gamma                78.742(7)
_cell_volume                     640.6(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6046
_cell_measurement_temperature    161.60
_cell_measurement_theta_max      34.42
_cell_measurement_theta_min      2.99
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.416
_exptl_absorpt_correction_T_max  0.3669
_exptl_absorpt_correction_T_min  0.2208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1430 before and 0.0983 after correction.
The Ratio of minimum to maximum transmission is 0.6018.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_unetI/netI     0.0871
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5740
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.873
_diffrn_reflns_theta_min         2.989
_diffrn_ambient_temperature      161.60
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2616
_reflns_number_total             2909
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2909
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0751
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1570P)²+0.1497P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2096
_refine_ls_wR_factor_ref         0.2177
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H3-C3
 1.08 with sigma of 0.02
 H2-N2
 1.01 with sigma of 0.02
3.a Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.31575(8) 0.07316(6) 0.65820(5) 0.0288(3) Uani 1 1 d . . . . .
S2 S 0.85269(8) 0.39940(7) -0.04139(6) 0.0306(3) Uani 1 1 d . . . . .
O3 O 0.3030(3) 0.2428(2) 0.63400(19) 0.0433(5) Uani 1 1 d . . . . .
O2 O 0.6475(3) 0.2845(2) 0.2467(2) 0.0407(5) Uani 1 1 d . . . . .
O1 O 0.1986(3) 0.6516(2) 0.4764(2) 0.0421(5) Uani 1 1 d . . . . .
N2 N 0.4103(3) 0.4399(2) 0.3949(2) 0.0324(5) Uani 1 1 d D . . . .
C5 C 0.5604(3) 0.5476(2) 0.1660(2) 0.0220(5) Uani 1 1 d . . . . .
C3 C 0.7126(3) 0.6821(3) -0.0794(2) 0.0284(5) Uani 1 1 d D . . . .
C6 C 0.4266(3) 0.6549(2) 0.2373(2) 0.0244(5) Uani 1 1 d . . . . .
C4 C 0.6925(3) 0.5540(2) 0.0244(2) 0.0232(4) Uani 1 1 d . . . . .
N1 N 0.3341(4) 0.9341(3) 0.1601(3) 0.0473(6) Uani 1 1 d . . . . .
C9 C 0.5504(3) 0.4056(2) 0.2700(2) 0.0267(5) Uani 1 1 d . . . . .
C8 C 0.3265(3) 0.5890(3) 0.3840(2) 0.0290(5) Uani 1 1 d . . . . .
C7 C 0.3774(3) 0.8090(3) 0.1928(3) 0.0313(5) Uani 1 1 d . . . . .
C11 C 0.1633(4) 0.0387(3) 0.8368(3) 0.0394(6) Uani 1 1 d . . . . .
C2 C 0.8598(4) 0.6442(3) -0.2070(3) 0.0370(6) Uani 1 1 d . . . . .
C1 C 0.9447(4) 0.4976(4) -0.2006(3) 0.0366(6) Uani 1 1 d . . . . .
C10 C 0.1771(4) 0.0253(3) 0.5669(3) 0.0427(6) Uani 1 1 d . . . . .
H10A H 0.053541 0.088580 0.592486 0.064 Uiso 1 1 calc R U . . .
H10B H 0.160746 -0.080797 0.594165 0.064 Uiso 1 1 calc R U . . .
H10C H 0.240614 0.041581 0.463665 0.064 Uiso 1 1 calc R U . . .
H2A H 0.891(5) 0.717(4) -0.286(4) 0.051(10) Uiso 1 1 d . . . . .
H3 H 0.632(4) 0.785(2) -0.066(3) 0.040(8) Uiso 1 1 d D . . . .
H1 H 1.036(5) 0.457(4) -0.273(4) 0.048(10) Uiso 1 1 d . . . . .
H11A H 0.045(5) 0.111(4) 0.846(4) 0.048(10) Uiso 1 1 d . . . . .
H2 H 0.359(5) 0.367(4) 0.482(3) 0.055(11) Uiso 1 1 d D . . . .
H11B H 0.155(6) -0.050(5) 0.852(4) 0.057(11) Uiso 1 1 d . . . . .
H11C H 0.211(6) 0.074(5) 0.906(5) 0.068(12) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.5134(19) . ?
S1 C11 1.782(3) . ?
S1 C10 1.775(3) . ?
S2 C4 1.730(2) . ?
S2 C1 1.687(3) . ?
O2 C9 1.211(3) . ?
O1 C8 1.211(3) . ?
N2 C9 1.372(3) . ?
N2 C8 1.389(3) . ?
N2 H2 1.019(19) . ?
C5 C6 1.359(3) . ?
C5 C4 1.430(3) . ?
C5 C9 1.520(3) . ?
C3 C4 1.424(3) . ?
C3 C2 1.421(3) . ?
C3 H3 1.019(18) . ?
C6 C8 1.490(3) . ?
C6 C7 1.420(3) . ?
N1 C7 1.150(3) . ?
C11 H11A 1.00(4) . ?
C11 H11B 0.81(5) . ?
C11 H11C 1.00(4) . ?
C2 C1 1.368(4) . ?
C2 H2A 0.94(4) . ?
C1 H1 0.89(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
O3 S1 C11 103.85(12) . . ?
O3 S1 C10 106.32(13) . . ?
C10 S1 C11 98.71(15) . . ?
C1 S2 C4 92.15(12) . . ?
C9 N2 C8 111.19(18) . . ?
C9 N2 H2 127(2) . . ?
C8 N2 H2 122(2) . . ?
C6 C5 C4 131.2(2) . . ?
C6 C5 C9 106.01(19) . . ?
C4 C5 C9 122.78(19) . . ?
C4 C3 H3 125.7(18) . . ?
C2 C3 C4 109.9(2) . . ?
C2 C3 H3 124.4(18) . . ?
C5 C6 C8 109.6(2) . . ?
C5 C6 C7 130.1(2) . . ?
C7 C6 C8 120.3(2) . . ?
C5 C4 S2 122.18(15) . . ?
C3 C4 S2 111.29(17) . . ?
C3 C4 C5 126.5(2) . . ?
O2 C9 N2 126.4(2) . . ?
O2 C9 C5 126.4(2) . . ?
N2 C9 C5 107.20(19) . . ?
O1 C8 N2 126.4(2) . . ?
O1 C8 C6 127.6(2) . . ?
N2 C8 C6 106.0(2) . . ?
N1 C7 C6 178.3(3) . . ?
S1 C11 H11A 107(2) . . ?
S1 C11 H11B 108(3) . . ?
S1 C11 H11C 111(2) . . ?
H11A C11 H11B 117(3) . . ?
H11A C11 H11C 101(3) . . ?
H11B C11 H11C 113(4) . . ?
C3 C2 H2A 121(2) . . ?
C1 C2 C3 113.9(2) . . ?
C1 C2 H2A 126(2) . . ?
S2 C1 H1 123(3) . . ?
C2 C1 S2 112.8(2) . . ?
C2 C1 H1 124(3) . . ?
S1 C10 H10A 109.5 . . ?
S1 C10 H10B 109.5 . . ?
S1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
C5 C6 C8 O1 -179.5(3) . . . . ?
C5 C6 C8 N2 0.9(3) . . . . ?
C3 C2 C1 S2 -0.3(3) . . . . ?
C6 C5 C4 S2 179.21(19) . . . . ?
C6 C5 C4 C3 -0.5(4) . . . . ?
C6 C5 C9 O2 -180.0(2) . . . . ?
C6 C5 C9 N2 0.3(2) . . . . ?
C4 S2 C1 C2 0.2(2) . . . . ?
C4 C5 C6 C8 -179.8(2) . . . . ?
C4 C5 C6 C7 -0.7(4) . . . . ?
C4 C5 C9 O2 -0.7(4) . . . . ?
C4 C5 C9 N2 179.5(2) . . . . ?
C4 C3 C2 C1 0.3(3) . . . . ?
C9 N2 C8 O1 179.6(3) . . . . ?
C9 N2 C8 C6 -0.7(3) . . . . ?
C9 C5 C6 C8 -0.7(2) . . . . ?
C9 C5 C6 C7 178.4(2) . . . . ?
C9 C5 C4 S2 0.2(3) . . . . ?
C9 C5 C4 C3 -179.52(19) . . . . ?
C8 N2 C9 O2 -179.5(2) . . . . ?
C8 N2 C9 C5 0.3(3) . . . . ?
C7 C6 C8 O1 1.3(4) . . . . ?
C7 C6 C8 N2 -178.3(2) . . . . ?
C2 C3 C4 S2 -0.1(2) . . . . ?
C2 C3 C4 C5 179.7(2) . . . . ?
C1 S2 C4 C5 -179.9(2) . . . . ?
C1 S2 C4 C3 -0.08(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cu_sg_209c2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2403601'
_audit_update_record             
;
2024-11-18 deposited with the CCDC.	2025-05-05 downloaded from the CCDC.
;
_audit_creation_date             2024-11-18
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 N2 O3'
_chemical_formula_sum            'C12 H8 N2 O3'
_chemical_formula_weight         228.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1679(4)
_cell_length_b                   7.7218(4)
_cell_length_c                   10.2127(5)
_cell_angle_alpha                96.893(2)
_cell_angle_beta                 90.608(2)
_cell_angle_gamma                107.975(2)
_cell_volume                     533.11(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9098
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      67.91
_cell_measurement_theta_min      4.37
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.748
_exptl_absorpt_coefficient_mu    0.879
_exptl_absorpt_correction_T_max  0.5849
_exptl_absorpt_correction_T_min  0.4176
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1299 before and 0.0682 after correction.
The Ratio of minimum to maximum transmission is 0.7140.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15572
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.338
_diffrn_reflns_theta_min         4.366
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1763
_reflns_number_total             1949
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT V8.38A (Bruker AXS)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'Bruker SAINT V8.38A (Bruker AXS)'
_computing_molecular_graphics    'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_publication_material  'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick 2018)'
_computing_structure_solution    'SHELXT 2014/5(Sheldrick 2014)'
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.036(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1949
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0608
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1305P)²+0.0997P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1907
_refine_ls_wR_factor_ref         0.1951
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N004(H004), C008(H008), C00A(H00A), C00C(H00C), C00D(H00D)
2.b Idealised Me refined as rotating group:
 C00H(H00B,H00E,H00F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.3498(3) 0.2735(2) 0.05755(16) 0.0799(6) Uani 1 1 d . . . . .
O002 O 0.1412(3) 0.6375(3) 0.89508(17) 0.0869(6) Uani 1 1 d . . . . .
O003 O 0.4780(3) 0.8201(2) 0.3138(2) 0.0963(7) Uani 1 1 d . . . . .
N004 N 0.4255(3) 0.5712(3) 0.1580(2) 0.0752(6) Uani 1 1 d . . . . .
H004 H 0.473823 0.628069 0.092677 0.090 Uiso 1 1 calc R U . . .
C005 C 0.3107(3) 0.5077(3) 0.3653(2) 0.0584(5) Uani 1 1 d . . . . .
C006 C 0.2774(3) 0.3498(3) 0.2837(2) 0.0609(5) Uani 1 1 d . . . . .
C007 C 0.2679(3) 0.5438(3) 0.5024(2) 0.0580(5) Uani 1 1 d . . . . .
C008 C 0.2702(3) 0.7584(3) 0.6957(2) 0.0674(6) Uani 1 1 d . . . . .
H008 H 0.299718 0.879318 0.735215 0.081 Uiso 1 1 calc R U . . .
C009 C 0.1868(3) 0.6163(3) 0.7683(2) 0.0627(6) Uani 1 1 d . . . . .
C00A C 0.1831(3) 0.4015(3) 0.5764(2) 0.0640(6) Uani 1 1 d . . . . .
H00A H 0.153047 0.280519 0.536883 0.077 Uiso 1 1 calc R U . . .
C00B C 0.4128(3) 0.6560(3) 0.2817(2) 0.0665(6) Uani 1 1 d . . . . .
C00C C 0.3098(3) 0.7225(3) 0.5656(2) 0.0657(6) Uani 1 1 d . . . . .
H00C H 0.366063 0.820134 0.518652 0.079 Uiso 1 1 calc R U . . .
C00D C 0.1427(3) 0.4363(3) 0.7072(2) 0.0688(6) Uani 1 1 d . . . . .
H00D H 0.085904 0.339202 0.754563 0.083 Uiso 1 1 calc R U . . .
C00E C 0.1864(3) 0.1639(3) 0.3069(2) 0.0729(7) Uani 1 1 d . . . . .
C00F C 0.3514(3) 0.3840(3) 0.1518(2) 0.0678(6) Uani 1 1 d . . . . .
N00G N 0.1127(4) 0.0140(3) 0.3191(3) 0.1067(9) Uani 1 1 d . . . . .
C00H C 0.1869(5) 0.8178(4) 0.9649(3) 0.0920(8) Uani 1 1 d . . . . .
H00B H 0.117938 0.886157 0.922577 0.138 Uiso 1 1 calc R U . . .
H00E H 0.325687 0.878379 0.965120 0.138 Uiso 1 1 calc R U . . .
H00F H 0.147727 0.810225 1.054231 0.138 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
O001 C00F 1.204(3) . ?
O002 C009 1.342(3) . ?
O002 C00H 1.424(3) . ?
O003 C00B 1.210(3) . ?
N004 H004 0.8600 . ?
N004 C00B 1.368(3) . ?
N004 C00F 1.371(3) . ?
C005 C006 1.345(3) . ?
C005 C007 1.449(3) . ?
C005 C00B 1.518(3) . ?
C006 C00E 1.432(3) . ?
C006 C00F 1.477(3) . ?
C007 C00A 1.395(3) . ?
C007 C00C 1.392(3) . ?
C008 H008 0.9300 . ?
C008 C009 1.382(3) . ?
C008 C00C 1.375(3) . ?
C009 C00D 1.392(3) . ?
C00A H00A 0.9300 . ?
C00A C00D 1.383(3) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00E N00G 1.137(3) . ?
C00H H00B 0.9600 . ?
C00H H00E 0.9600 . ?
C00H H00F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C009 O002 C00H 119.3(2) . . ?
C00B N004 H004 124.4 . . ?
C00B N004 C00F 111.29(19) . . ?
C00F N004 H004 124.4 . . ?
C006 C005 C007 131.56(18) . . ?
C006 C005 C00B 104.35(18) . . ?
C007 C005 C00B 124.09(18) . . ?
C005 C006 C00E 130.23(19) . . ?
C005 C006 C00F 111.34(18) . . ?
C00E C006 C00F 118.43(18) . . ?
C00A C007 C005 121.57(19) . . ?
C00C C007 C005 121.22(19) . . ?
C00C C007 C00A 117.2(2) . . ?
C009 C008 H008 119.7 . . ?
C00C C008 H008 119.7 . . ?
C00C C008 C009 120.5(2) . . ?
O002 C009 C008 124.90(19) . . ?
O002 C009 C00D 116.24(19) . . ?
C008 C009 C00D 118.9(2) . . ?
C007 C00A H00A 119.3 . . ?
C00D C00A C007 121.42(19) . . ?
C00D C00A H00A 119.3 . . ?
O003 C00B N004 123.7(2) . . ?
O003 C00B C005 128.7(2) . . ?
N004 C00B C005 107.60(18) . . ?
C007 C00C H00C 119.1 . . ?
C008 C00C C007 121.8(2) . . ?
C008 C00C H00C 119.1 . . ?
C009 C00D H00D 119.9 . . ?
C00A C00D C009 120.22(19) . . ?
C00A C00D H00D 119.9 . . ?
N00G C00E C006 176.8(3) . . ?
O001 C00F N004 126.3(2) . . ?
O001 C00F C006 128.3(2) . . ?
N004 C00F C006 105.36(18) . . ?
O002 C00H H00B 109.5 . . ?
O002 C00H H00E 109.5 . . ?
O002 C00H H00F 109.5 . . ?
H00B C00H H00E 109.5 . . ?
H00B C00H H00F 109.5 . . ?
H00E C00H H00F 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
O002 C009 C00D C00A 179.5(2) . . . . ?
C005 C006 C00F O001 177.8(2) . . . . ?
C005 C006 C00F N004 -1.7(2) . . . . ?
C005 C007 C00A C00D 179.88(18) . . . . ?
C005 C007 C00C C008 -179.87(19) . . . . ?
C006 C005 C007 C00A 2.7(4) . . . . ?
C006 C005 C007 C00C -177.3(2) . . . . ?
C006 C005 C00B O003 -177.0(3) . . . . ?
C006 C005 C00B N004 1.4(2) . . . . ?
C007 C005 C006 C00E 0.3(4) . . . . ?
C007 C005 C006 C00F -179.1(2) . . . . ?
C007 C005 C00B O003 2.4(4) . . . . ?
C007 C005 C00B N004 -179.21(18) . . . . ?
C007 C00A C00D C009 -0.1(3) . . . . ?
C008 C009 C00D C00A 0.3(3) . . . . ?
C009 C008 C00C C007 0.1(4) . . . . ?
C00A C007 C00C C008 0.2(3) . . . . ?
C00B N004 C00F O001 -176.9(2) . . . . ?
C00B N004 C00F C006 2.6(3) . . . . ?
C00B C005 C006 C00E 179.6(2) . . . . ?
C00B C005 C006 C00F 0.2(2) . . . . ?
C00B C005 C007 C00A -176.54(18) . . . . ?
C00B C005 C007 C00C 3.5(3) . . . . ?
C00C C007 C00A C00D -0.1(3) . . . . ?
C00C C008 C009 O002 -179.4(2) . . . . ?
C00C C008 C009 C00D -0.3(3) . . . . ?
C00E C006 C00F O001 -1.7(4) . . . . ?
C00E C006 C00F N004 178.79(19) . . . . ?
C00F N004 C00B O003 175.9(2) . . . . ?
C00F N004 C00B C005 -2.6(3) . . . . ?
C00H O002 C009 C008 -2.6(4) . . . . ?
C00H O002 C009 C00D 178.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
