# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2465401'
loop_
_audit_author_name
_audit_author_address
'Aidar Gubaidullin'
;Arbuzov Institute of Organic and Physical Chemistry of RAS
Russia
;
_audit_update_record             
;
2025-06-18 deposited with the CCDC.	2025-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(E)-3-(2-(2-nitrophenyl)-2-oxoethylidene)-3,4-dihydroquinoxalin-2(1H)-one
_chemical_name_common            ?
_chemical_melting_point          274-275
_chemical_formula_moiety         'C16 H11 N3 O4'
_chemical_formula_sum            'C16 H11 N3 O4'
_chemical_formula_weight         309.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   20.296(11)
_cell_length_b                   12.509(7)
_cell_length_c                   14.318(13)
_cell_angle_alpha                90
_cell_angle_beta                 130.660(10)
_cell_angle_gamma                90
_cell_volume                     2758(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    302
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      19.58
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5842
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
 G.M. Sheldrick (1998a). SADABS v.2.01, Bruker.
 Siemens Area Detector Absorption Correction Program.
 Bruker AXS. Madison. Wisconsin. USA
  Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
  SADABS-2016/2, J. Appl. Cryst. 48 (2015) 3-10. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus I\mS DIAMOND Mo X-ray tube'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_detector                 'area detector PHOTON III'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6914
_diffrn_reflns_av_unetI/netI     0.2318
_diffrn_reflns_av_R_equivalents  0.1742
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.098
_diffrn_reflns_theta_max         27.284
_diffrn_reflns_theta_full        26.500
_diffrn_measured_fraction_theta_max 0.790
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.790
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.790
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2457
_reflns_number_gt                1200
_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       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0610P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.027(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2457
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1673
_refine_ls_R_factor_gt           0.0992
_refine_ls_wR_factor_ref         0.2897
_refine_ls_wR_factor_gt          0.2275
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_restrained_S_all      0.953
_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
C2 C 0.3734(3) 0.2589(4) 0.5599(4) 0.0425(13) Uani 1 1 d . . . . .
C3 C 0.4643(3) 0.2657(4) 0.6090(4) 0.0418(12) Uani 1 1 d . . . . .
C3A C 0.4998(3) 0.3648(4) 0.6273(4) 0.0430(12) Uani 1 1 d . . . . .
H3A H 0.4656 0.4265 0.6073 0.052 Uiso 1 1 calc R U . . .
C3B C 0.5870(3) 0.3777(4) 0.6755(5) 0.0437(13) Uani 1 1 d . . . . .
C4A C 0.4706(3) 0.0726(4) 0.6050(4) 0.0423(13) Uani 1 1 d . . . . .
C5 C 0.5168(3) -0.0196(4) 0.6266(5) 0.0501(14) Uani 1 1 d . . . . .
H5 H 0.5763 -0.0151 0.6644 0.060 Uiso 1 1 calc R U . . .
C6 C 0.4768(3) -0.1163(4) 0.5936(5) 0.0495(14) Uani 1 1 d . . . . .
H6 H 0.5088 -0.1793 0.6093 0.059 Uiso 1 1 calc R U . . .
C7 C 0.3898(4) -0.1238(4) 0.5371(5) 0.0496(14) Uani 1 1 d . . . . .
H7 H 0.3623 -0.1918 0.5129 0.060 Uiso 1 1 calc R U . . .
C8 C 0.3427(3) -0.0338(4) 0.5159(5) 0.0487(14) Uani 1 1 d . . . . .
H8 H 0.2832 -0.0396 0.4777 0.058 Uiso 1 1 calc R U . . .
C8A C 0.3831(3) 0.0659(4) 0.5509(4) 0.0409(12) Uani 1 1 d . . . . .
C31 C 0.6203(3) 0.4907(4) 0.6966(4) 0.0409(12) Uani 1 1 d . . . . .
C32 C 0.6737(3) 0.5251(4) 0.6740(5) 0.0451(13) Uani 1 1 d . . . . .
C33 C 0.7102(3) 0.6252(4) 0.7046(5) 0.0501(14) Uani 1 1 d . . . . .
H33 H 0.7478 0.6438 0.6894 0.060 Uiso 1 1 calc R U . . .
C34 C 0.6926(4) 0.6982(5) 0.7569(5) 0.0592(16) Uani 1 1 d . . . . .
H34 H 0.7166 0.7681 0.7765 0.071 Uiso 1 1 calc R U . . .
C35 C 0.6383(4) 0.6676(4) 0.7812(5) 0.0577(16) Uani 1 1 d . . . . .
H35 H 0.6246 0.7171 0.8167 0.069 Uiso 1 1 calc R U . . .
C36 C 0.6050(4) 0.5648(4) 0.7530(5) 0.0546(15) Uani 1 1 d . . . . .
H36 H 0.5704 0.5441 0.7729 0.066 Uiso 1 1 calc R U . . .
N1 N 0.3390(3) 0.1599(3) 0.5331(4) 0.0479(12) Uani 1 1 d . . . . .
N4 N 0.5076(3) 0.1741(3) 0.6327(4) 0.0434(11) Uani 1 1 d . . . . .
N32 N 0.6884(3) 0.4567(4) 0.6057(4) 0.0499(12) Uani 1 1 d . . . . .
O2 O 0.3331(2) 0.3404(3) 0.5470(3) 0.0471(10) Uani 1 1 d . . . . .
O32 O 0.6266(3) 0.4081(3) 0.5152(4) 0.0596(11) Uani 1 1 d . . . . .
O33 O 0.7634(2) 0.4502(3) 0.6449(4) 0.0667(13) Uani 1 1 d . . . . .
O3B O 0.6377(2) 0.3022(3) 0.7025(3) 0.0506(11) Uani 1 1 d . . . . .
H1 H 0.282(3) 0.156(3) 0.500(4) 0.034(12) Uiso 1 1 d . . . . .
H4 H 0.569(4) 0.185(4) 0.660(5) 0.060(15) 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
C2 O2 1.244(6) . ?
C2 N1 1.348(6) . ?
C2 C3 1.488(7) . ?
C3 N4 1.346(6) . ?
C3 C3A 1.371(7) . ?
C3A C3B 1.429(7) . ?
C3A H3A 0.9500 . ?
C3B O3B 1.257(6) . ?
C3B C31 1.509(7) . ?
C4A C5 1.388(7) . ?
C4A N4 1.396(6) . ?
C4A C8A 1.403(7) . ?
C5 C6 1.359(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.376(7) . ?
C7 H7 0.9500 . ?
C8 C8A 1.394(7) . ?
C8 H8 0.9500 . ?
C8A N1 1.396(6) . ?
C31 C32 1.387(7) . ?
C31 C36 1.391(7) . ?
C32 C33 1.373(7) . ?
C32 N32 1.468(7) . ?
C33 C34 1.367(8) . ?
C33 H33 0.9500 . ?
C34 C35 1.408(8) . ?
C34 H34 0.9500 . ?
C35 C36 1.385(8) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
N1 H1 0.92(5) . ?
N4 H4 1.05(6) . ?
N32 O32 1.226(5) . ?
N32 O33 1.235(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C2 N1 122.9(5) . . ?
O2 C2 C3 121.0(4) . . ?
N1 C2 C3 116.1(4) . . ?
N4 C3 C3A 123.0(5) . . ?
N4 C3 C2 118.4(4) . . ?
C3A C3 C2 118.6(5) . . ?
C3 C3A C3B 121.8(5) . . ?
C3 C3A H3A 119.1 . . ?
C3B C3A H3A 119.1 . . ?
O3B C3B C3A 124.8(5) . . ?
O3B C3B C31 118.2(4) . . ?
C3A C3B C31 117.0(5) . . ?
C5 C4A N4 122.1(5) . . ?
C5 C4A C8A 120.2(5) . . ?
N4 C4A C8A 117.7(5) . . ?
C6 C5 C4A 119.8(5) . . ?
C6 C5 H5 120.1 . . ?
C4A C5 H5 120.1 . . ?
C5 C6 C7 120.6(5) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 120.7(5) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C8A 119.5(5) . . ?
C7 C8 H8 120.3 . . ?
C8A C8 H8 120.3 . . ?
C8 C8A N1 122.1(5) . . ?
C8 C8A C4A 119.2(5) . . ?
N1 C8A C4A 118.7(4) . . ?
C32 C31 C36 115.6(5) . . ?
C32 C31 C3B 124.0(4) . . ?
C36 C31 C3B 120.0(5) . . ?
C33 C32 C31 123.3(5) . . ?
C33 C32 N32 116.3(4) . . ?
C31 C32 N32 120.2(4) . . ?
C34 C33 C32 120.4(5) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C33 C34 C35 118.7(5) . . ?
C33 C34 H34 120.7 . . ?
C35 C34 H34 120.7 . . ?
C36 C35 C34 119.4(5) . . ?
C36 C35 H35 120.3 . . ?
C34 C35 H35 120.3 . . ?
C35 C36 C31 122.6(5) . . ?
C35 C36 H36 118.7 . . ?
C31 C36 H36 118.7 . . ?
C2 N1 C8A 124.7(4) . . ?
C2 N1 H1 116(3) . . ?
C8A N1 H1 119(3) . . ?
C3 N4 C4A 124.1(5) . . ?
C3 N4 H4 114(3) . . ?
C4A N4 H4 121(3) . . ?
O32 N32 O33 123.9(5) . . ?
O32 N32 C32 118.7(4) . . ?
O33 N32 C32 117.4(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
O2 C2 C3 N4 173.3(4) . . . . ?
N1 C2 C3 N4 -5.4(7) . . . . ?
O2 C2 C3 C3A -7.1(7) . . . . ?
N1 C2 C3 C3A 174.2(5) . . . . ?
N4 C3 C3A C3B -1.2(8) . . . . ?
C2 C3 C3A C3B 179.2(4) . . . . ?
C3 C3A C3B O3B 1.7(8) . . . . ?
C3 C3A C3B C31 -177.6(4) . . . . ?
N4 C4A C5 C6 -177.5(4) . . . . ?
C8A C4A C5 C6 1.0(8) . . . . ?
C4A C5 C6 C7 0.7(8) . . . . ?
C5 C6 C7 C8 -1.4(8) . . . . ?
C6 C7 C8 C8A 0.4(8) . . . . ?
C7 C8 C8A N1 -179.2(5) . . . . ?
C7 C8 C8A C4A 1.3(8) . . . . ?
C5 C4A C8A C8 -2.0(7) . . . . ?
N4 C4A C8A C8 176.5(4) . . . . ?
C5 C4A C8A N1 178.5(5) . . . . ?
N4 C4A C8A N1 -3.0(7) . . . . ?
O3B C3B C31 C32 39.1(7) . . . . ?
C3A C3B C31 C32 -141.6(5) . . . . ?
O3B C3B C31 C36 -134.3(5) . . . . ?
C3A C3B C31 C36 45.0(7) . . . . ?
C36 C31 C32 C33 0.1(7) . . . . ?
C3B C31 C32 C33 -173.5(5) . . . . ?
C36 C31 C32 N32 -174.9(5) . . . . ?
C3B C31 C32 N32 11.5(7) . . . . ?
C31 C32 C33 C34 -2.0(8) . . . . ?
N32 C32 C33 C34 173.2(5) . . . . ?
C32 C33 C34 C35 1.5(8) . . . . ?
C33 C34 C35 C36 0.7(8) . . . . ?
C34 C35 C36 C31 -2.6(8) . . . . ?
C32 C31 C36 C35 2.2(8) . . . . ?
C3B C31 C36 C35 176.1(5) . . . . ?
O2 C2 N1 C8A -177.2(5) . . . . ?
C3 C2 N1 C8A 1.5(7) . . . . ?
C8 C8A N1 C2 -176.8(5) . . . . ?
C4A C8A N1 C2 2.7(7) . . . . ?
C3A C3 N4 C4A -174.2(5) . . . . ?
C2 C3 N4 C4A 5.4(7) . . . . ?
C5 C4A N4 C3 177.3(5) . . . . ?
C8A C4A N4 C3 -1.2(7) . . . . ?
C33 C32 N32 O32 -133.8(5) . . . . ?
C31 C32 N32 O32 41.6(7) . . . . ?
C33 C32 N32 O33 47.5(6) . . . . ?
C31 C32 N32 O33 -137.1(5) . . . . ?

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.074


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dimethylformamide'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2465403'
loop_
_audit_author_name
_audit_author_address
'Aidar Gubaidullin'
;Arbuzov Institute of Organic and Physical Chemistry of RAS
Russia
;
_audit_update_record             
;
2025-06-18 deposited with the CCDC.	2025-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(E)-3-(2-(2-aminophenyl)-2-oxoethylidene)-3,4-dihydroquinoxalin-2(1H)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 N3 O2'
_chemical_formula_sum            'C16 H13 N3 O2'
_chemical_formula_weight         279.29

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                   14.5549(17)
_cell_length_b                   5.3336(7)
_cell_length_c                   17.269(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.412(6)
_cell_angle_gamma                90
_cell_volume                     1286.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2861
_cell_measurement_theta_min      4.09
_cell_measurement_theta_max      25.35
_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5324
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   
;
 G.M. Sheldrick (1998a). SADABS v.2.01, Bruker.
 Siemens Area Detector Absorption Correction Program.
 Bruker AXS. Madison. Wisconsin. USA
  Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
  SADABS-2016/2, J. Appl. Cryst. 48 (2015) 3-10. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus I\mS DIAMOND Mo X-ray tube'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_detector                 'area detector PHOTON III'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26457
_diffrn_reflns_av_unetI/netI     0.0946
_diffrn_reflns_av_R_equivalents  0.1266
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.918
_diffrn_reflns_theta_max         30.124
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3686
_reflns_number_gt                2309
_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       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0389P)²+1.0058P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3686
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1259
_refine_ls_R_factor_gt           0.0703
_refine_ls_wR_factor_ref         0.1654
_refine_ls_wR_factor_gt          0.1378
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
C2 C 0.61555(14) 0.7137(4) 0.72442(14) 0.0278(5) Uani 1 1 d . . . . .
C3 C 0.51683(14) 0.6194(4) 0.71639(13) 0.0257(5) Uani 1 1 d . . . . .
C3A C 0.48007(14) 0.4356(4) 0.66175(14) 0.0284(5) Uani 1 1 d . . . . .
H3A H 0.5169 0.3791 0.6277 0.034 Uiso 1 1 calc R U . . .
C3B C 0.38781(14) 0.3226(4) 0.65316(14) 0.0276(5) Uani 1 1 d . . . . .
C4A C 0.50330(13) 0.9158(4) 0.81935(13) 0.0259(5) Uani 1 1 d . . . . .
C5 C 0.45178(15) 1.0096(4) 0.86939(15) 0.0343(5) Uani 1 1 d . . . . .
H5 H 0.3913 0.9396 0.8680 0.041 Uiso 1 1 calc R U . . .
C6 C 0.48870(17) 1.2048(5) 0.92111(16) 0.0405(6) Uani 1 1 d . . . . .
H6 H 0.4536 1.2682 0.9556 0.049 Uiso 1 1 calc R U . . .
C7 C 0.57691(16) 1.3098(5) 0.92322(16) 0.0390(6) Uani 1 1 d . . . . .
H7 H 0.6012 1.4462 0.9584 0.047 Uiso 1 1 calc R U . . .
C8 C 0.62904(15) 1.2165(4) 0.87439(15) 0.0334(5) Uani 1 1 d . . . . .
H8 H 0.6895 1.2873 0.8761 0.040 Uiso 1 1 calc R U . . .
C8A C 0.59277(13) 1.0180(4) 0.82253(14) 0.0269(5) Uani 1 1 d . . . . .
C31 C 0.35348(14) 0.1284(4) 0.59053(14) 0.0267(5) Uani 1 1 d . . . . .
C32 C 0.28570(14) -0.0546(4) 0.59818(14) 0.0291(5) Uani 1 1 d . . . . .
C33 C 0.26197(15) -0.2467(4) 0.54025(15) 0.0335(5) Uani 1 1 d . . . . .
H33 H 0.2193 -0.3756 0.5460 0.040 Uiso 1 1 calc R U . . .
C34 C 0.29918(15) -0.2518(4) 0.47542(15) 0.0347(5) Uani 1 1 d . . . . .
H34 H 0.2822 -0.3840 0.4372 0.042 Uiso 1 1 calc R U . . .
C35 C 0.36150(16) -0.0652(4) 0.46538(15) 0.0344(5) Uani 1 1 d . . . . .
H35 H 0.3851 -0.0651 0.4194 0.041 Uiso 1 1 calc R U . . .
C36 C 0.38844(15) 0.1196(4) 0.52319(15) 0.0319(5) Uani 1 1 d . . . . .
H36 H 0.4322 0.2449 0.5170 0.038 Uiso 1 1 calc R U . . .
N1 N 0.64473(12) 0.9108(4) 0.77400(12) 0.0295(4) Uani 1 1 d . . . . .
N4 N 0.46907(12) 0.7231(4) 0.76548(12) 0.0284(4) Uani 1 1 d . . . . .
N32 N 0.24511(14) -0.0503(4) 0.66054(14) 0.0426(6) Uani 1 1 d . . . . .
H321 H 0.2041 -0.1677 0.6644 0.051 Uiso 1 1 calc R U . . .
H322 H 0.2599 0.0699 0.6969 0.051 Uiso 1 1 calc R U . . .
O1 O 0.66749(10) 0.6147(3) 0.68767(10) 0.0365(4) Uani 1 1 d . . . . .
O3B O 0.33853(10) 0.3841(3) 0.69983(10) 0.0345(4) Uani 1 1 d . . . . .
H1 H 0.702(2) 0.978(5) 0.7782(17) 0.048(8) Uiso 1 1 d . . . . .
H4 H 0.4115(19) 0.653(5) 0.7613(17) 0.050(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
C2 O1 1.234(3) . ?
C2 N1 1.347(3) . ?
C2 C3 1.491(3) . ?
C3 N4 1.357(3) . ?
C3 C3A 1.361(3) . ?
C3A C3B 1.441(3) . ?
C3A H3A 0.9500 . ?
C3B O3B 1.264(3) . ?
C3B C31 1.479(3) . ?
C4A N4 1.381(3) . ?
C4A C5 1.388(3) . ?
C4A C8A 1.398(3) . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.377(3) . ?
C7 H7 0.9500 . ?
C8 C8A 1.391(3) . ?
C8 H8 0.9500 . ?
C8A N1 1.400(3) . ?
C31 C36 1.396(3) . ?
C31 C32 1.420(3) . ?
C32 N32 1.367(3) . ?
C32 C33 1.405(3) . ?
C33 C34 1.375(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.390(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.379(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
N1 H1 0.90(3) . ?
N4 H4 0.90(3) . ?
N32 H321 0.8800 . ?
N32 H322 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C2 N1 122.11(19) . . ?
O1 C2 C3 121.5(2) . . ?
N1 C2 C3 116.41(19) . . ?
N4 C3 C3A 123.79(19) . . ?
N4 C3 C2 117.06(19) . . ?
C3A C3 C2 119.14(19) . . ?
C3 C3A C3B 123.0(2) . . ?
C3 C3A H3A 118.5 . . ?
C3B C3A H3A 118.5 . . ?
O3B C3B C3A 120.4(2) . . ?
O3B C3B C31 120.85(19) . . ?
C3A C3B C31 118.73(19) . . ?
N4 C4A C5 122.15(19) . . ?
N4 C4A C8A 118.11(19) . . ?
C5 C4A C8A 119.7(2) . . ?
C6 C5 C4A 119.7(2) . . ?
C6 C5 H5 120.1 . . ?
C4A C5 H5 120.1 . . ?
C5 C6 C7 120.6(2) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C8A 119.7(2) . . ?
C7 C8 H8 120.2 . . ?
C8A C8 H8 120.2 . . ?
C8 C8A C4A 120.1(2) . . ?
C8 C8A N1 121.70(19) . . ?
C4A C8A N1 118.2(2) . . ?
C36 C31 C32 118.7(2) . . ?
C36 C31 C3B 120.38(19) . . ?
C32 C31 C3B 120.9(2) . . ?
N32 C32 C33 120.0(2) . . ?
N32 C32 C31 121.9(2) . . ?
C33 C32 C31 118.2(2) . . ?
C34 C33 C32 121.3(2) . . ?
C34 C33 H33 119.3 . . ?
C32 C33 H33 119.3 . . ?
C33 C34 C35 120.6(2) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C36 C35 C34 118.9(2) . . ?
C36 C35 H35 120.5 . . ?
C34 C35 H35 120.5 . . ?
C35 C36 C31 122.1(2) . . ?
C35 C36 H36 119.0 . . ?
C31 C36 H36 119.0 . . ?
C2 N1 C8A 124.96(18) . . ?
C2 N1 H1 118.8(18) . . ?
C8A N1 H1 116.2(18) . . ?
C3 N4 C4A 124.97(18) . . ?
C3 N4 H4 114.2(18) . . ?
C4A N4 H4 120.8(18) . . ?
C32 N32 H321 120.0 . . ?
C32 N32 H322 120.0 . . ?
H321 N32 H322 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 N4 173.3(2) . . . . ?
N1 C2 C3 N4 -6.4(3) . . . . ?
O1 C2 C3 C3A -6.1(3) . . . . ?
N1 C2 C3 C3A 174.1(2) . . . . ?
N4 C3 C3A C3B -3.2(3) . . . . ?
C2 C3 C3A C3B 176.2(2) . . . . ?
C3 C3A C3B O3B -3.3(3) . . . . ?
C3 C3A C3B C31 178.5(2) . . . . ?
N4 C4A C5 C6 -179.0(2) . . . . ?
C8A C4A C5 C6 0.8(4) . . . . ?
C4A C5 C6 C7 0.4(4) . . . . ?
C5 C6 C7 C8 -1.1(4) . . . . ?
C6 C7 C8 C8A 0.5(4) . . . . ?
C7 C8 C8A C4A 0.7(3) . . . . ?
C7 C8 C8A N1 -177.6(2) . . . . ?
N4 C4A C8A C8 178.4(2) . . . . ?
C5 C4A C8A C8 -1.4(3) . . . . ?
N4 C4A C8A N1 -3.2(3) . . . . ?
C5 C4A C8A N1 177.0(2) . . . . ?
O3B C3B C31 C36 158.0(2) . . . . ?
C3A C3B C31 C36 -23.9(3) . . . . ?
O3B C3B C31 C32 -23.0(3) . . . . ?
C3A C3B C31 C32 155.1(2) . . . . ?
C36 C31 C32 N32 -176.9(2) . . . . ?
C3B C31 C32 N32 4.1(3) . . . . ?
C36 C31 C32 C33 4.3(3) . . . . ?
C3B C31 C32 C33 -174.71(19) . . . . ?
N32 C32 C33 C34 177.9(2) . . . . ?
C31 C32 C33 C34 -3.3(3) . . . . ?
C32 C33 C34 C35 -0.2(3) . . . . ?
C33 C34 C35 C36 2.6(3) . . . . ?
C34 C35 C36 C31 -1.4(3) . . . . ?
C32 C31 C36 C35 -2.0(3) . . . . ?
C3B C31 C36 C35 177.00(19) . . . . ?
O1 C2 N1 C8A -174.3(2) . . . . ?
C3 C2 N1 C8A 5.4(3) . . . . ?
C8 C8A N1 C2 177.8(2) . . . . ?
C4A C8A N1 C2 -0.6(3) . . . . ?
C3A C3 N4 C4A -177.6(2) . . . . ?
C2 C3 N4 C4A 3.1(3) . . . . ?
C5 C4A N4 C3 -178.4(2) . . . . ?
C8A C4A N4 C3 1.8(3) . . . . ?

_refine_diff_density_max         0.347
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.056


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dimethyl sulfoxide'
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2465404'
loop_
_audit_author_name
_audit_author_address
'Aidar Gubaidullin'
;Arbuzov Institute of Organic and Physical Chemistry of RAS
Russia
;
_audit_update_record             
;
2025-06-18 deposited with the CCDC.	2025-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1?,4?-dihydro-1H,3?H-spiro[quinoline-2,2?-quinoxaline]-3?,4(3H)-dione DMSO solvate'
_chemical_name_common            spiro[quinoline-2,2?-quinoxaline]
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 N3 O2, C2 H6 O S'
_chemical_formula_sum            'C18 H19 N3 O3 S'
_chemical_formula_weight         357.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9238(5)
_cell_length_b                   9.7738(6)
_cell_length_c                   11.3393(7)
_cell_angle_alpha                96.093(2)
_cell_angle_beta                 102.819(2)
_cell_angle_gamma                95.935(2)
_cell_volume                     844.12(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9921
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      29.08
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.086
_exptl_absorpt_coefficient_mu    0.215
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6084
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   
;
 G.M. Sheldrick (1998a). SADABS v.2.01, Bruker.
 Siemens Area Detector Absorption Correction Program.
 Bruker AXS. Madison. Wisconsin. USA
  Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
  SADABS-2016/2, J. Appl. Cryst. 48 (2015) 3-10. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus I\mS DIAMOND Mo X-ray tube'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_detector                 'area detector PHOTON III'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35370
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.623
_diffrn_reflns_theta_max         29.155
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4521
_reflns_number_gt                3671
_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       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0907P)²+0.2499P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4521
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1532
_refine_ls_wR_factor_gt          0.1393
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
C1S C 0.1761(3) 0.8351(2) 0.5632(2) 0.0440(5) Uani 1 1 d . . . . .
H11S H 0.2842 0.8772 0.6217 0.066 Uiso 1 1 calc R U . . .
H12S H 0.0861 0.8966 0.5640 0.066 Uiso 1 1 calc R U . . .
H13S H 0.1976 0.8212 0.4812 0.066 Uiso 1 1 calc R U . . .
C2 C 0.3562(2) 0.51400(17) 0.17361(15) 0.0228(3) Uani 1 1 d . . . . .
C2S C 0.1138(3) 0.7302(2) 0.75988(18) 0.0369(5) Uani 1 1 d . . . . .
H21S H 0.0761 0.6519 0.7994 0.055 Uiso 1 1 calc R U . . .
H22S H 0.0367 0.8018 0.7647 0.055 Uiso 1 1 calc R U . . .
H23S H 0.2339 0.7691 0.8014 0.055 Uiso 1 1 calc R U . . .
C3 C 0.2753(2) 0.59276(17) 0.07085(15) 0.0250(3) Uani 1 1 d . . . . .
H31 H 0.2788 0.5404 -0.0081 0.030 Uiso 1 1 calc R U . . .
H32 H 0.1511 0.5967 0.0715 0.030 Uiso 1 1 calc R U . . .
C4 C 0.3645(2) 0.73890(18) 0.07898(15) 0.0249(3) Uani 1 1 d . . . . .
C4A C 0.5556(2) 0.75879(17) 0.12440(15) 0.0239(3) Uani 1 1 d . . . . .
C5 C 0.6559(3) 0.87914(19) 0.10874(17) 0.0306(4) Uani 1 1 d . . . . .
H5 H 0.5988 0.9513 0.0740 0.037 Uiso 1 1 calc R U . . .
C6 C 0.8349(3) 0.8950(2) 0.14255(19) 0.0351(4) Uani 1 1 d . . . . .
H6 H 0.9014 0.9751 0.1275 0.042 Uiso 1 1 calc R U . . .
C7 C 0.9177(3) 0.7921(2) 0.19924(19) 0.0337(4) Uani 1 1 d . . . . .
H7 H 1.0414 0.8034 0.2247 0.040 Uiso 1 1 calc R U . . .
C8 C 0.8218(2) 0.67370(19) 0.21878(17) 0.0293(4) Uani 1 1 d . . . . .
H8 H 0.8800 0.6054 0.2591 0.035 Uiso 1 1 calc R U . . .
C8A C 0.6389(2) 0.65372(17) 0.17933(15) 0.0234(3) Uani 1 1 d . . . . .
C23 C 0.3165(2) 0.57579(17) 0.29352(15) 0.0220(3) Uani 1 1 d . . . . .
C24A C 0.3240(2) 0.34738(17) 0.35877(16) 0.0225(3) Uani 1 1 d . . . . .
C25 C 0.3404(2) 0.26762(18) 0.45380(16) 0.0269(4) Uani 1 1 d . . . . .
H25 H 0.3479 0.3099 0.5345 0.032 Uiso 1 1 calc R U . . .
C26 C 0.3457(3) 0.12675(19) 0.43115(19) 0.0323(4) Uani 1 1 d . . . . .
H26 H 0.3573 0.0724 0.4964 0.039 Uiso 1 1 calc R U . . .
C27 C 0.3342(3) 0.06430(19) 0.31341(19) 0.0341(4) Uani 1 1 d . . . . .
H27 H 0.3378 -0.0327 0.2983 0.041 Uiso 1 1 calc R U . . .
C28 C 0.3175(2) 0.14334(19) 0.21742(18) 0.0303(4) Uani 1 1 d . . . . .
H28 H 0.3101 0.1003 0.1370 0.036 Uiso 1 1 calc R U . . .
C28A C 0.3116(2) 0.28579(17) 0.23914(16) 0.0244(3) Uani 1 1 d . . . . .
N1 N 0.5463(2) 0.52826(15) 0.18930(14) 0.0241(3) Uani 1 1 d . . . . .
N21 N 0.2807(2) 0.36974(15) 0.14606(14) 0.0271(3) Uani 1 1 d . . . . .
N24 N 0.3110(2) 0.48937(15) 0.37825(13) 0.0239(3) Uani 1 1 d . . . . .
O1S O 0.25304(17) 0.58684(13) 0.60723(11) 0.0296(3) Uani 1 1 d . . . . .
O2 O 0.29976(17) 0.69911(12) 0.31084(11) 0.0284(3) Uani 1 1 d . . . . .
O4 O 0.28307(18) 0.83045(14) 0.04083(12) 0.0336(3) Uani 1 1 d . . . . .
S1S S 0.10401(6) 0.67205(4) 0.60436(4) 0.02695(15) Uani 1 1 d . . . . .
H1 H 0.596(3) 0.488(2) 0.246(2) 0.034(6) Uiso 1 1 d . . . . .
H21 H 0.289(3) 0.329(2) 0.074(2) 0.033(6) Uiso 1 1 d . . . . .
H24 H 0.302(3) 0.526(3) 0.449(2) 0.044(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1S S1S 1.781(2) . ?
C1S H11S 0.9800 . ?
C1S H12S 0.9800 . ?
C1S H13S 0.9800 . ?
C2 N21 1.447(2) . ?
C2 N1 1.467(2) . ?
C2 C3 1.524(2) . ?
C2 C23 1.539(2) . ?
C2S S1S 1.7767(19) . ?
C2S H21S 0.9800 . ?
C2S H22S 0.9800 . ?
C2S H23S 0.9800 . ?
C3 C4 1.511(2) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
C4 O4 1.217(2) . ?
C4 C4A 1.473(2) . ?
C4A C5 1.400(2) . ?
C4A C8A 1.404(2) . ?
C5 C6 1.372(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(3) . ?
C7 H7 0.9500 . ?
C8 C8A 1.405(3) . ?
C8 H8 0.9500 . ?
C8A N1 1.391(2) . ?
C23 O2 1.226(2) . ?
C23 N24 1.350(2) . ?
C24A C25 1.387(2) . ?
C24A N24 1.400(2) . ?
C24A C28A 1.403(2) . ?
C25 C26 1.380(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.387(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.391(3) . ?
C27 H27 0.9500 . ?
C28 C28A 1.395(2) . ?
C28 H28 0.9500 . ?
C28A N21 1.399(2) . ?
N1 H1 0.83(2) . ?
N21 H21 0.89(2) . ?
N24 H24 0.87(3) . ?
O1S S1S 1.5104(13) . ?

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
S1S C1S H11S 109.5 . . ?
S1S C1S H12S 109.5 . . ?
H11S C1S H12S 109.5 . . ?
S1S C1S H13S 109.5 . . ?
H11S C1S H13S 109.5 . . ?
H12S C1S H13S 109.5 . . ?
N21 C2 N1 111.17(14) . . ?
N21 C2 C3 109.37(14) . . ?
N1 C2 C3 109.86(13) . . ?
N21 C2 C23 108.70(13) . . ?
N1 C2 C23 108.38(13) . . ?
C3 C2 C23 109.33(14) . . ?
S1S C2S H21S 109.5 . . ?
S1S C2S H22S 109.5 . . ?
H21S C2S H22S 109.5 . . ?
S1S C2S H23S 109.5 . . ?
H21S C2S H23S 109.5 . . ?
H22S C2S H23S 109.5 . . ?
C4 C3 C2 114.15(14) . . ?
C4 C3 H31 108.7 . . ?
C2 C3 H31 108.7 . . ?
C4 C3 H32 108.7 . . ?
C2 C3 H32 108.7 . . ?
H31 C3 H32 107.6 . . ?
O4 C4 C4A 122.90(16) . . ?
O4 C4 C3 121.11(16) . . ?
C4A C4 C3 115.73(15) . . ?
C5 C4A C8A 119.62(16) . . ?
C5 C4A C4 120.56(16) . . ?
C8A C4A C4 119.77(15) . . ?
C6 C5 C4A 121.35(18) . . ?
C6 C5 H5 119.3 . . ?
C4A C5 H5 119.3 . . ?
C5 C6 C7 119.09(18) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 120.78(18) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C8A 120.45(17) . . ?
C7 C8 H8 119.8 . . ?
C8A C8 H8 119.8 . . ?
N1 C8A C4A 121.83(16) . . ?
N1 C8A C8 119.45(16) . . ?
C4A C8A C8 118.62(16) . . ?
O2 C23 N24 123.15(15) . . ?
O2 C23 C2 120.28(15) . . ?
N24 C23 C2 116.47(14) . . ?
C25 C24A N24 121.22(15) . . ?
C25 C24A C28A 120.46(16) . . ?
N24 C24A C28A 118.25(15) . . ?
C26 C25 C24A 120.01(17) . . ?
C26 C25 H25 120.0 . . ?
C24A C25 H25 120.0 . . ?
C25 C26 C27 120.25(18) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C28 120.19(17) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C27 C28 C28A 120.09(17) . . ?
C27 C28 H28 120.0 . . ?
C28A C28 H28 120.0 . . ?
C28 C28A C24A 119.00(16) . . ?
C28 C28A N21 123.24(16) . . ?
C24A C28A N21 117.59(15) . . ?
C8A N1 C2 120.68(14) . . ?
C8A N1 H1 113.8(15) . . ?
C2 N1 H1 112.9(15) . . ?
C28A N21 C2 118.09(14) . . ?
C28A N21 H21 113.7(15) . . ?
C2 N21 H21 114.0(14) . . ?
C23 N24 C24A 123.97(14) . . ?
C23 N24 H24 116.7(17) . . ?
C24A N24 H24 119.3(17) . . ?
O1S S1S C2S 105.04(9) . . ?
O1S S1S C1S 106.00(10) . . ?
C2S S1S C1S 97.36(10) . . ?

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
N21 C2 C3 C4 -170.45(14) . . . . ?
N1 C2 C3 C4 -48.18(18) . . . . ?
C23 C2 C3 C4 70.64(18) . . . . ?
C2 C3 C4 O4 -149.05(16) . . . . ?
C2 C3 C4 C4A 36.6(2) . . . . ?
O4 C4 C4A C5 -9.6(3) . . . . ?
C3 C4 C4A C5 164.63(15) . . . . ?
O4 C4 C4A C8A 173.05(16) . . . . ?
C3 C4 C4A C8A -12.7(2) . . . . ?
C8A C4A C5 C6 2.1(3) . . . . ?
C4 C4A C5 C6 -175.26(17) . . . . ?
C4A C5 C6 C7 -3.3(3) . . . . ?
C5 C6 C7 C8 1.5(3) . . . . ?
C6 C7 C8 C8A 1.4(3) . . . . ?
C5 C4A C8A N1 -175.44(15) . . . . ?
C4 C4A C8A N1 1.9(2) . . . . ?
C5 C4A C8A C8 0.9(3) . . . . ?
C4 C4A C8A C8 178.23(15) . . . . ?
C7 C8 C8A N1 173.84(16) . . . . ?
C7 C8 C8A C4A -2.6(3) . . . . ?
N21 C2 C23 O2 -149.74(16) . . . . ?
N1 C2 C23 O2 89.31(19) . . . . ?
C3 C2 C23 O2 -30.4(2) . . . . ?
N21 C2 C23 N24 33.7(2) . . . . ?
N1 C2 C23 N24 -87.25(17) . . . . ?
C3 C2 C23 N24 153.02(15) . . . . ?
N24 C24A C25 C26 177.34(16) . . . . ?
C28A C24A C25 C26 0.4(3) . . . . ?
C24A C25 C26 C27 -0.2(3) . . . . ?
C25 C26 C27 C28 0.1(3) . . . . ?
C26 C27 C28 C28A -0.2(3) . . . . ?
C27 C28 C28A C24A 0.4(3) . . . . ?
C27 C28 C28A N21 -174.58(17) . . . . ?
C25 C24A C28A C28 -0.5(3) . . . . ?
N24 C24A C28A C28 -177.53(16) . . . . ?
C25 C24A C28A N21 174.75(15) . . . . ?
N24 C24A C28A N21 -2.2(2) . . . . ?
C4A C8A N1 C2 -16.6(2) . . . . ?
C8 C8A N1 C2 167.06(15) . . . . ?
N21 C2 N1 C8A 160.33(14) . . . . ?
C3 C2 N1 C8A 39.1(2) . . . . ?
C23 C2 N1 C8A -80.26(18) . . . . ?
C28 C28A N21 C2 -150.72(17) . . . . ?
C24A C28A N21 C2 34.2(2) . . . . ?
N1 C2 N21 C28A 70.87(19) . . . . ?
C3 C2 N21 C28A -167.64(14) . . . . ?
C23 C2 N21 C28A -48.3(2) . . . . ?
O2 C23 N24 C24A 177.79(16) . . . . ?
C2 C23 N24 C24A -5.8(2) . . . . ?
C25 C24A N24 C23 171.50(16) . . . . ?
C28A C24A N24 C23 -11.5(3) . . . . ?

_refine_diff_density_max         0.634
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.085


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dimethyl sulfoxide and CHCl3'
####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2465402'
loop_
_audit_author_name
_audit_author_address
'Aidar Gubaidullin'
;Arbuzov Institute of Organic and Physical Chemistry of RAS
Russia
;
_audit_update_record             
;
2025-06-18 deposited with the CCDC.	2025-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(E)-3-(2-(2-nitrophenyl)-2-oxoethylidene)-3,4-dihydroquinoxalin-2(1H)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C16 H13 N3 O2), C2 H6 O S'
_chemical_formula_sum            'C34 H32 N6 O5 S'
_chemical_formula_weight         636.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   11.750(5)
_cell_length_b                   7.054(5)
_cell_length_c                   37.400(16)
_cell_angle_alpha                90
_cell_angle_beta                 91.70(2)
_cell_angle_gamma                90
_cell_volume                     3098(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    369
_cell_measurement_theta_min      3.77
_cell_measurement_theta_max      19.34
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.158
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5360
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   
;
 G.M. Sheldrick (1998a). SADABS v.2.01, Bruker.
 Siemens Area Detector Absorption Correction Program.
 Bruker AXS. Madison. Wisconsin. USA
  Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
  SADABS-2016/2, J. Appl. Cryst. 48 (2015) 3-10. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus I\mS DIAMOND Mo X-ray tube'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_detector                 'area detector PHOTON III'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16428
_diffrn_reflns_av_unetI/netI     0.3042
_diffrn_reflns_av_R_equivalents  0.2108
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         2.939
_diffrn_reflns_theta_max         28.279
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             6513
_reflns_number_gt                2277
_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       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0010P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0102(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6513
_refine_ls_number_parameters     434
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2769
_refine_ls_R_factor_gt           0.1137
_refine_ls_wR_factor_ref         0.2552
_refine_ls_wR_factor_gt          0.1802
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_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
C1S C 0.8591(6) 1.0987(10) 0.2451(2) 0.063(2) Uani 1 1 d . . . . .
H01A H 0.8570 1.2327 0.2382 0.095 Uiso 1 1 calc R U . . .
H12S H 0.8724 1.0886 0.2710 0.095 Uiso 1 1 calc R U . . .
H13S H 0.7863 1.0388 0.2384 0.095 Uiso 1 1 calc R U . . .
C2A C 0.9511(5) 0.1057(8) 0.45162(15) 0.0226(14) Uani 1 1 d . . . . .
C2B C 0.5494(5) 0.1205(9) 0.04714(18) 0.0302(15) Uani 1 1 d . . . . .
C2BA C 0.6968(5) 0.2619(8) 0.08708(18) 0.0320(16) Uani 1 1 d . . . . .
H2BA H 0.7456 0.2562 0.0673 0.038 Uiso 1 1 calc R U . . .
C2S C 0.9086(6) 0.9935(10) 0.1791(2) 0.062(2) Uani 1 1 d . . . . .
H21S H 0.9085 1.1248 0.1705 0.094 Uiso 1 1 calc R U . . .
H22S H 0.8302 0.9461 0.1793 0.094 Uiso 1 1 calc R U . . .
H23S H 0.9534 0.9147 0.1632 0.094 Uiso 1 1 calc R U . . .
C3A C 0.9091(5) 0.1876(8) 0.41745(16) 0.0251(14) Uani 1 1 d . . . . .
C3B C 0.5859(5) 0.1992(8) 0.08267(17) 0.0281(15) Uani 1 1 d . . . . .
C3AA C 0.9799(5) 0.1915(8) 0.38907(16) 0.0262(15) Uani 1 1 d . . . . .
H3AA H 1.0544 0.1406 0.3920 0.031 Uiso 1 1 calc R U . . .
C3AB C 0.9448(5) 0.2713(8) 0.35431(17) 0.0261(15) Uani 1 1 d . . . . .
C3BB C 0.7410(5) 0.3357(8) 0.12061(16) 0.0245(14) Uani 1 1 d . . . . .
C4AA C 0.7286(5) 0.2550(8) 0.44396(17) 0.0294(16) Uani 1 1 d . . . . .
C4BA C 0.4008(5) 0.1243(9) 0.10511(18) 0.0315(16) Uani 1 1 d . . . . .
C5A C 0.6188(5) 0.3280(9) 0.43993(18) 0.0350(17) Uani 1 1 d . . . . .
H5A H 0.5933 0.3838 0.4180 0.042 Uiso 1 1 calc R U . . .
C5B C 0.3289(5) 0.1215(9) 0.13413(18) 0.0366(17) Uani 1 1 d . . . . .
H5B H 0.3516 0.1783 0.1562 0.044 Uiso 1 1 calc R U . . .
C6A C 0.5489(6) 0.3171(11) 0.4683(2) 0.049(2) Uani 1 1 d . . . . .
H6A H 0.4741 0.3680 0.4662 0.058 Uiso 1 1 calc R U . . .
C6B C 0.2246(5) 0.0347(10) 0.13005(19) 0.0423(18) Uani 1 1 d . . . . .
H6B H 0.1750 0.0306 0.1496 0.051 Uiso 1 1 calc R U . . .
C7A C 0.5846(6) 0.2335(11) 0.5002(2) 0.051(2) Uani 1 1 d . . . . .
H7A H 0.5340 0.2251 0.5195 0.062 Uiso 1 1 calc R U . . .
C7B C 0.1909(6) -0.0467(10) 0.0977(2) 0.045(2) Uani 1 1 d . . . . .
H7B H 0.1183 -0.1057 0.0953 0.054 Uiso 1 1 calc R U . . .
C8A C 0.6931(5) 0.1629(10) 0.50401(18) 0.0411(18) Uani 1 1 d . . . . .
H8A H 0.7179 0.1070 0.5260 0.049 Uiso 1 1 calc R U . . .
C8B C 0.2613(5) -0.0430(9) 0.06906(18) 0.0383(17) Uani 1 1 d . . . . .
H8B H 0.2378 -0.0985 0.0469 0.046 Uiso 1 1 calc R U . . .
C8AA C 0.7661(5) 0.1727(9) 0.47596(16) 0.0284(15) Uani 1 1 d . . . . .
C8BA C 0.3680(5) 0.0436(8) 0.07291(17) 0.0285(15) Uani 1 1 d . . . . .
C31A C 1.0283(5) 0.2650(8) 0.32541(15) 0.0220(14) Uani 1 1 d . . . . .
C31B C 0.8620(5) 0.3938(9) 0.12338(18) 0.0322(16) Uani 1 1 d . . . . .
C32A C 1.0252(5) 0.4093(8) 0.29874(16) 0.0268(15) Uani 1 1 d . . . . .
C32B C 0.9079(5) 0.4825(9) 0.15463(16) 0.0307(16) Uani 1 1 d . . . . .
C33A C 1.1089(5) 0.4026(9) 0.27268(17) 0.0346(17) Uani 1 1 d . . . . .
H33A H 1.1095 0.4979 0.2547 0.042 Uiso 1 1 calc R U . . .
C33B C 1.0223(5) 0.5350(9) 0.15629(19) 0.0395(18) Uani 1 1 d . . . . .
H33B H 1.0527 0.5960 0.1771 0.047 Uiso 1 1 calc R U . . .
C34A C 1.1890(6) 0.2640(10) 0.27241(18) 0.0421(19) Uani 1 1 d . . . . .
H34A H 1.2452 0.2654 0.2547 0.051 Uiso 1 1 calc R U . . .
C34B C 1.0911(5) 0.4996(9) 0.12822(19) 0.0397(18) Uani 1 1 d . . . . .
H34B H 1.1692 0.5337 0.1302 0.048 Uiso 1 1 calc R U . . .
C35A C 1.1895(5) 0.1192(9) 0.29791(17) 0.0375(17) Uani 1 1 d . . . . .
H35A H 1.2439 0.0198 0.2971 0.045 Uiso 1 1 calc R U . . .
C35B C 1.0499(6) 0.4156(10) 0.09717(19) 0.046(2) Uani 1 1 d . . . . .
H35B H 1.0983 0.3931 0.0777 0.055 Uiso 1 1 calc R U . . .
C36A C 1.1102(5) 0.1224(9) 0.32429(16) 0.0285(15) Uani 1 1 d . . . . .
H36A H 1.1114 0.0258 0.3420 0.034 Uiso 1 1 calc R U . . .
C36B C 0.9350(5) 0.3645(9) 0.09519(17) 0.0337(16) Uani 1 1 d . . . . .
H36B H 0.9055 0.3076 0.0738 0.040 Uiso 1 1 calc R U . . .
N1A N 0.8764(4) 0.1077(6) 0.47886(13) 0.0256(12) Uani 1 1 d . . . . .
H1A H 0.9005 0.0642 0.4998 0.031 Uiso 1 1 calc R U . . .
N1B N 0.4433(4) 0.0499(6) 0.04482(14) 0.0294(13) Uani 1 1 d . . . . .
H1B H 0.4195 0.0043 0.0240 0.035 Uiso 1 1 calc R U . . .
N4A N 0.8017(4) 0.2612(7) 0.41538(14) 0.0259(13) Uani 1 1 d . . . . .
N4B N 0.5109(4) 0.1994(7) 0.10911(15) 0.0278(13) Uani 1 1 d . . . . .
N32A N 0.9492(5) 0.5509(8) 0.29780(16) 0.0447(18) Uani 1 1 d . . . . .
N32B N 0.8445(4) 0.5109(7) 0.18463(14) 0.0368(14) Uani 1 1 d . . . . .
H32B H 0.8765 0.5608 0.2040 0.044 Uiso 1 1 calc R U . . .
H32D H 0.7721 0.4791 0.1844 0.044 Uiso 1 1 calc R U . . .
O1S O 0.9622(4) 0.7791(6) 0.23385(13) 0.0548(15) Uani 1 1 d . . . . .
O002 O 1.0475(3) 0.0416(6) 0.45555(11) 0.0295(11) Uani 1 1 d . . . . .
O3AB O 0.8517(3) 0.3513(6) 0.35028(11) 0.0350(11) Uani 1 1 d . . . . .
O3BB O 0.6796(3) 0.3460(6) 0.14691(11) 0.0337(11) Uani 1 1 d . . . . .
O004 O 0.6129(3) 0.1228(6) 0.02154(12) 0.0359(11) Uani 1 1 d . . . . .
S1S S 0.96943(16) 0.9844(3) 0.22309(5) 0.0478(6) Uani 1 1 d . . . . .
H4A H 0.783(6) 0.309(11) 0.388(2) 0.10(3) Uiso 1 1 d . . . . .
H4B H 0.537(5) 0.260(8) 0.1303(16) 0.029(18) Uiso 1 1 d . . . . .
H32A H 0.885(4) 0.552(7) 0.3134(14) 0.016(14) Uiso 1 1 d . . . . .
H32C H 0.962(4) 0.652(7) 0.2837(14) 0.009(13) 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
C1S S1S 1.752(7) . ?
C1S H01A 0.9800 . ?
C1S H12S 0.9800 . ?
C1S H13S 0.9800 . ?
C2A O002 1.225(6) . ?
C2A N1A 1.364(6) . ?
C2A C3A 1.474(8) . ?
C2B O004 1.231(7) . ?
C2B N1B 1.343(7) . ?
C2B C3B 1.491(9) . ?
C2BA C3B 1.382(8) . ?
C2BA C3BB 1.441(8) . ?
C2BA H2BA 0.9500 . ?
C2S S1S 1.775(8) . ?
C2S H21S 0.9800 . ?
C2S H22S 0.9800 . ?
C2S H23S 0.9800 . ?
C3A N4A 1.365(7) . ?
C3A C3AA 1.368(7) . ?
C3B N4B 1.344(7) . ?
C3AA C3AB 1.464(8) . ?
C3AA H3AA 0.9500 . ?
C3AB O3AB 1.236(7) . ?
C3AB C31A 1.482(7) . ?
C3BB O3BB 1.239(6) . ?
C3BB C31B 1.480(8) . ?
C4AA C8AA 1.390(8) . ?
C4AA N4A 1.392(7) . ?
C4AA C5A 1.393(8) . ?
C4BA C8BA 1.377(9) . ?
C4BA C5B 1.395(8) . ?
C4BA N4B 1.401(8) . ?
C5A C6A 1.364(8) . ?
C5A H5A 0.9500 . ?
C5B C6B 1.375(8) . ?
C5B H5B 0.9500 . ?
C6A C7A 1.385(10) . ?
C6A H6A 0.9500 . ?
C6B C7B 1.387(9) . ?
C6B H6B 0.9500 . ?
C7A C8A 1.372(9) . ?
C7A H7A 0.9500 . ?
C7B C8B 1.372(8) . ?
C7B H7B 0.9500 . ?
C8A C8AA 1.376(8) . ?
C8A H8A 0.9500 . ?
C8B C8BA 1.398(8) . ?
C8B H8B 0.9500 . ?
C8AA N1A 1.376(7) . ?
C8BA N1B 1.394(7) . ?
C31A C36A 1.394(7) . ?
C31A C32A 1.425(8) . ?
C31B C36B 1.394(8) . ?
C31B C32B 1.418(9) . ?
C32A N32A 1.340(7) . ?
C32A C33A 1.406(8) . ?
C32B N32B 1.380(7) . ?
C32B C33B 1.394(8) . ?
C33A C34A 1.357(8) . ?
C33A H33A 0.9500 . ?
C33B C34B 1.367(8) . ?
C33B H33B 0.9500 . ?
C34A C35A 1.397(9) . ?
C34A H34A 0.9500 . ?
C34B C35B 1.378(9) . ?
C34B H34B 0.9500 . ?
C35A C36A 1.377(7) . ?
C35A H35A 0.9500 . ?
C35B C36B 1.398(8) . ?
C35B H35B 0.9500 . ?
C36A H36A 0.9500 . ?
C36B H36B 0.9500 . ?
N1A H1A 0.8800 . ?
N1B H1B 0.8800 . ?
N4A H4A 1.10(9) . ?
N4B H4B 0.94(6) . ?
N32A H32A 0.96(4) . ?
N32A H32C 0.90(5) . ?
N32B H32B 0.8800 . ?
N32B H32D 0.8800 . ?
O1S S1S 1.506(5) . ?

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
S1S C1S H01A 109.5 . . ?
S1S C1S H12S 109.5 . . ?
H01A C1S H12S 109.5 . . ?
S1S C1S H13S 109.5 . . ?
H01A C1S H13S 109.5 . . ?
H12S C1S H13S 109.5 . . ?
O002 C2A N1A 121.8(5) . . ?
O002 C2A C3A 122.2(5) . . ?
N1A C2A C3A 116.0(5) . . ?
O004 C2B N1B 122.5(6) . . ?
O004 C2B C3B 121.6(6) . . ?
N1B C2B C3B 115.9(5) . . ?
C3B C2BA C3BB 122.3(6) . . ?
C3B C2BA H2BA 118.9 . . ?
C3BB C2BA H2BA 118.9 . . ?
S1S C2S H21S 109.5 . . ?
S1S C2S H22S 109.5 . . ?
H21S C2S H22S 109.5 . . ?
S1S C2S H23S 109.5 . . ?
H21S C2S H23S 109.5 . . ?
H22S C2S H23S 109.5 . . ?
N4A C3A C3AA 122.0(6) . . ?
N4A C3A C2A 118.9(5) . . ?
C3AA C3A C2A 119.0(6) . . ?
N4B C3B C2BA 123.3(6) . . ?
N4B C3B C2B 118.6(6) . . ?
C2BA C3B C2B 118.1(5) . . ?
C3A C3AA C3AB 122.3(6) . . ?
C3A C3AA H3AA 118.8 . . ?
C3AB C3AA H3AA 118.8 . . ?
O3AB C3AB C3AA 120.6(5) . . ?
O3AB C3AB C31A 121.8(6) . . ?
C3AA C3AB C31A 117.4(5) . . ?
O3BB C3BB C2BA 120.6(6) . . ?
O3BB C3BB C31B 120.6(6) . . ?
C2BA C3BB C31B 118.8(5) . . ?
C8AA C4AA N4A 119.1(6) . . ?
C8AA C4AA C5A 121.1(6) . . ?
N4A C4AA C5A 119.8(6) . . ?
C8BA C4BA C5B 121.0(6) . . ?
C8BA C4BA N4B 118.9(5) . . ?
C5B C4BA N4B 120.0(6) . . ?
C6A C5A C4AA 118.2(6) . . ?
C6A C5A H5A 120.9 . . ?
C4AA C5A H5A 120.9 . . ?
C6B C5B C4BA 118.6(7) . . ?
C6B C5B H5B 120.7 . . ?
C4BA C5B H5B 120.7 . . ?
C5A C6A C7A 121.4(6) . . ?
C5A C6A H6A 119.3 . . ?
C7A C6A H6A 119.3 . . ?
C5B C6B C7B 120.8(6) . . ?
C5B C6B H6B 119.6 . . ?
C7B C6B H6B 119.6 . . ?
C8A C7A C6A 120.0(6) . . ?
C8A C7A H7A 120.0 . . ?
C6A C7A H7A 120.0 . . ?
C8B C7B C6B 120.6(6) . . ?
C8B C7B H7B 119.7 . . ?
C6B C7B H7B 119.7 . . ?
C7A C8A C8AA 120.1(7) . . ?
C7A C8A H8A 120.0 . . ?
C8AA C8A H8A 120.0 . . ?
C7B C8B C8BA 119.2(7) . . ?
C7B C8B H8B 120.4 . . ?
C8BA C8B H8B 120.4 . . ?
C8A C8AA N1A 122.0(6) . . ?
C8A C8AA C4AA 119.3(6) . . ?
N1A C8AA C4AA 118.7(5) . . ?
C4BA C8BA N1B 118.6(6) . . ?
C4BA C8BA C8B 119.8(6) . . ?
N1B C8BA C8B 121.6(6) . . ?
C36A C31A C32A 119.9(5) . . ?
C36A C31A C3AB 121.1(5) . . ?
C32A C31A C3AB 119.0(5) . . ?
C36B C31B C32B 117.4(6) . . ?
C36B C31B C3BB 121.2(6) . . ?
C32B C31B C3BB 121.4(6) . . ?
N32A C32A C33A 119.1(6) . . ?
N32A C32A C31A 123.6(5) . . ?
C33A C32A C31A 117.2(5) . . ?
N32B C32B C33B 117.9(6) . . ?
N32B C32B C31B 122.2(5) . . ?
C33B C32B C31B 119.8(6) . . ?
C34A C33A C32A 121.9(6) . . ?
C34A C33A H33A 119.0 . . ?
C32A C33A H33A 119.0 . . ?
C34B C33B C32B 120.6(7) . . ?
C34B C33B H33B 119.7 . . ?
C32B C33B H33B 119.7 . . ?
C33A C34A C35A 120.7(6) . . ?
C33A C34A H34A 119.6 . . ?
C35A C34A H34A 119.6 . . ?
C33B C34B C35B 121.7(6) . . ?
C33B C34B H34B 119.2 . . ?
C35B C34B H34B 119.2 . . ?
C36A C35A C34A 119.2(6) . . ?
C36A C35A H35A 120.4 . . ?
C34A C35A H35A 120.4 . . ?
C34B C35B C36B 118.0(6) . . ?
C34B C35B H35B 121.0 . . ?
C36B C35B H35B 121.0 . . ?
C35A C36A C31A 121.0(6) . . ?
C35A C36A H36A 119.5 . . ?
C31A C36A H36A 119.5 . . ?
C31B C36B C35B 122.5(6) . . ?
C31B C36B H36B 118.8 . . ?
C35B C36B H36B 118.8 . . ?
C2A N1A C8AA 124.7(5) . . ?
C2A N1A H1A 117.6 . . ?
C8AA N1A H1A 117.6 . . ?
C2B N1B C8BA 124.9(6) . . ?
C2B N1B H1B 117.5 . . ?
C8BA N1B H1B 117.5 . . ?
C3A N4A C4AA 122.4(6) . . ?
C3A N4A H4A 109(4) . . ?
C4AA N4A H4A 128(4) . . ?
C3B N4B C4BA 123.0(6) . . ?
C3B N4B H4B 114(3) . . ?
C4BA N4B H4B 122(3) . . ?
C32A N32A H32A 121(3) . . ?
C32A N32A H32C 119(3) . . ?
H32A N32A H32C 120(4) . . ?
C32B N32B H32B 120.0 . . ?
C32B N32B H32D 120.0 . . ?
H32B N32B H32D 120.0 . . ?
O1S S1S C1S 105.6(3) . . ?
O1S S1S C2S 105.0(3) . . ?
C1S S1S C2S 97.8(4) . . ?

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 C2A C3A N4A -178.2(5) . . . . ?
N1A C2A C3A N4A 1.0(8) . . . . ?
O002 C2A C3A C3AA 0.3(9) . . . . ?
N1A C2A C3A C3AA 179.5(5) . . . . ?
C3BB C2BA C3B N4B -0.9(10) . . . . ?
C3BB C2BA C3B C2B -178.4(6) . . . . ?
O004 C2B C3B N4B 177.3(6) . . . . ?
N1B C2B C3B N4B -1.8(9) . . . . ?
O004 C2B C3B C2BA -5.0(10) . . . . ?
N1B C2B C3B C2BA 175.8(5) . . . . ?
N4A C3A C3AA C3AB -1.2(9) . . . . ?
C2A C3A C3AA C3AB -179.7(6) . . . . ?
C3A C3AA C3AB O3AB 5.4(10) . . . . ?
C3A C3AA C3AB C31A -179.1(5) . . . . ?
C3B C2BA C3BB O3BB -0.3(10) . . . . ?
C3B C2BA C3BB C31B 177.9(6) . . . . ?
C8AA C4AA C5A C6A 0.2(10) . . . . ?
N4A C4AA C5A C6A 179.1(6) . . . . ?
C8BA C4BA C5B C6B 0.6(10) . . . . ?
N4B C4BA C5B C6B -175.4(6) . . . . ?
C4AA C5A C6A C7A -1.0(12) . . . . ?
C4BA C5B C6B C7B -0.6(10) . . . . ?
C5A C6A C7A C8A 1.3(13) . . . . ?
C5B C6B C7B C8B 0.2(11) . . . . ?
C6A C7A C8A C8AA -0.8(12) . . . . ?
C6B C7B C8B C8BA 0.2(11) . . . . ?
C7A C8A C8AA N1A 178.4(6) . . . . ?
C7A C8A C8AA C4AA 0.1(10) . . . . ?
N4A C4AA C8AA C8A -178.6(6) . . . . ?
C5A C4AA C8AA C8A 0.3(10) . . . . ?
N4A C4AA C8AA N1A 2.9(9) . . . . ?
C5A C4AA C8AA N1A -178.2(6) . . . . ?
C5B C4BA C8BA N1B -179.8(5) . . . . ?
N4B C4BA C8BA N1B -3.8(9) . . . . ?
C5B C4BA C8BA C8B -0.1(10) . . . . ?
N4B C4BA C8BA C8B 175.9(5) . . . . ?
C7B C8B C8BA C4BA -0.3(10) . . . . ?
C7B C8B C8BA N1B 179.4(6) . . . . ?
O3AB C3AB C31A C36A -155.6(6) . . . . ?
C3AA C3AB C31A C36A 29.0(8) . . . . ?
O3AB C3AB C31A C32A 25.2(9) . . . . ?
C3AA C3AB C31A C32A -150.2(6) . . . . ?
O3BB C3BB C31B C36B 173.2(6) . . . . ?
C2BA C3BB C31B C36B -5.0(9) . . . . ?
O3BB C3BB C31B C32B -7.3(9) . . . . ?
C2BA C3BB C31B C32B 174.5(6) . . . . ?
C36A C31A C32A N32A 179.8(6) . . . . ?
C3AB C31A C32A N32A -1.1(9) . . . . ?
C36A C31A C32A C33A -1.7(9) . . . . ?
C3AB C31A C32A C33A 177.4(5) . . . . ?
C36B C31B C32B N32B -177.2(6) . . . . ?
C3BB C31B C32B N32B 3.3(10) . . . . ?
C36B C31B C32B C33B -0.5(10) . . . . ?
C3BB C31B C32B C33B 179.9(6) . . . . ?
N32A C32A C33A C34A 179.3(7) . . . . ?
C31A C32A C33A C34A 0.8(10) . . . . ?
N32B C32B C33B C34B 175.9(6) . . . . ?
C31B C32B C33B C34B -0.9(10) . . . . ?
C32A C33A C34A C35A 1.3(11) . . . . ?
C32B C33B C34B C35B 1.6(11) . . . . ?
C33A C34A C35A C36A -2.4(11) . . . . ?
C33B C34B C35B C36B -0.8(11) . . . . ?
C34A C35A C36A C31A 1.4(10) . . . . ?
C32A C31A C36A C35A 0.7(9) . . . . ?
C3AB C31A C36A C35A -178.4(6) . . . . ?
C32B C31B C36B C35B 1.3(10) . . . . ?
C3BB C31B C36B C35B -179.2(6) . . . . ?
C34B C35B C36B C31B -0.6(11) . . . . ?
O002 C2A N1A C8AA -178.1(6) . . . . ?
C3A C2A N1A C8AA 2.7(8) . . . . ?
C8A C8AA N1A C2A 176.9(6) . . . . ?
C4AA C8AA N1A C2A -4.7(9) . . . . ?
O004 C2B N1B C8BA 179.9(6) . . . . ?
C3B C2B N1B C8BA -0.9(9) . . . . ?
C4BA C8BA N1B C2B 3.8(9) . . . . ?
C8B C8BA N1B C2B -175.9(6) . . . . ?
C3AA C3A N4A C4AA 178.9(6) . . . . ?
C2A C3A N4A C4AA -2.6(9) . . . . ?
C8AA C4AA N4A C3A 0.6(9) . . . . ?
C5A C4AA N4A C3A -178.3(6) . . . . ?
C2BA C3B N4B C4BA -175.7(6) . . . . ?
C2B C3B N4B C4BA 1.8(9) . . . . ?
C8BA C4BA N4B C3B 1.1(9) . . . . ?
C5B C4BA N4B C3B 177.2(6) . . . . ?

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.073

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dimethyl sulfoxide'
####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2465405'
loop_
_audit_author_name
_audit_author_address
'Aidar Gubaidullin'
;Arbuzov Institute of Organic and Physical Chemistry of RAS
Russia
;
_audit_update_record             
;
2025-06-18 deposited with the CCDC.	2025-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'2-(benzimidazol-2-yl)quinolin-4(1H)-one DMF solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H11 N3 O, C3 H7 N O'
_chemical_formula_sum            'C19 H18 N4 O2'
_chemical_formula_weight         334.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   10.447(3)
_cell_length_b                   9.520(3)
_cell_length_c                   17.134(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.142(12)
_cell_angle_gamma                90
_cell_volume                     1691.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6375
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      28.18
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4313
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   
;
 G.M. Sheldrick (1998a). SADABS v.2.01, Bruker.
 Siemens Area Detector Absorption Correction Program.
 Bruker AXS. Madison. Wisconsin. USA
  Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
  SADABS-2016/2, J. Appl. Cryst. 48 (2015) 3-10. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus I\mS DIAMOND Mo X-ray tube'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_detector                 'area detector PHOTON III'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34134
_diffrn_reflns_av_unetI/netI     0.0881
_diffrn_reflns_av_R_equivalents  0.1300
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.905
_diffrn_reflns_theta_max         29.235
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4519
_reflns_number_gt                2865
_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       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0692P)²+1.3053P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4519
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1257
_refine_ls_R_factor_gt           0.0756
_refine_ls_wR_factor_ref         0.1970
_refine_ls_wR_factor_gt          0.1668
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
C1S C 0.6641(2) 0.2247(3) 0.48273(16) 0.0411(6) Uani 1 1 d . . . . .
H1S H 0.6120 0.1918 0.5206 0.049 Uiso 1 1 calc R U . . .
C2 C 0.2667(2) 0.3977(2) 0.46605(13) 0.0314(5) Uani 1 1 d . . . . .
C2S C 0.8280(3) 0.0618(3) 0.54149(18) 0.0510(7) Uani 1 1 d . . . . .
H21S H 0.7620 0.0438 0.5762 0.076 Uiso 1 1 calc R U . . .
H22S H 0.9071 0.0950 0.5728 0.076 Uiso 1 1 calc R U . . .
H23S H 0.8461 -0.0251 0.5142 0.076 Uiso 1 1 calc R U . . .
C3 C 0.1528(2) 0.4707(2) 0.45106(14) 0.0342(5) Uani 1 1 d . . . . .
H3 H 0.0844 0.4496 0.4809 0.041 Uiso 1 1 calc R U . . .
C3S C 0.8654(3) 0.2095(3) 0.42656(19) 0.0545(7) Uani 1 1 d . . . . .
H31S H 0.9479 0.2424 0.4539 0.082 Uiso 1 1 calc R U . . .
H32S H 0.8247 0.2852 0.3935 0.082 Uiso 1 1 calc R U . . .
H33S H 0.8802 0.1285 0.3935 0.082 Uiso 1 1 calc R U . . .
C4 C 0.1342(2) 0.5769(2) 0.39233(13) 0.0334(5) Uani 1 1 d . . . . .
C4A C 0.2424(2) 0.5985(2) 0.34690(13) 0.0324(5) Uani 1 1 d . . . . .
C5 C 0.2370(3) 0.7000(3) 0.28635(14) 0.0401(6) Uani 1 1 d . . . . .
H5 H 0.1610 0.7547 0.2743 0.048 Uiso 1 1 calc R U . . .
C6 C 0.3390(3) 0.7209(3) 0.24487(16) 0.0478(7) Uani 1 1 d . . . . .
H6 H 0.3333 0.7891 0.2041 0.057 Uiso 1 1 calc R U . . .
C7 C 0.4525(3) 0.6413(3) 0.26260(16) 0.0485(7) Uani 1 1 d . . . . .
H7 H 0.5236 0.6564 0.2340 0.058 Uiso 1 1 calc R U . . .
C8 C 0.4607(2) 0.5416(3) 0.32142(15) 0.0409(6) Uani 1 1 d . . . . .
H8 H 0.5373 0.4880 0.3333 0.049 Uiso 1 1 calc R U . . .
C8A C 0.3556(2) 0.5193(2) 0.36365(13) 0.0333(5) Uani 1 1 d . . . . .
C22 C 0.2887(2) 0.2933(2) 0.52897(14) 0.0343(5) Uani 1 1 d . . . . .
C23A C 0.3703(2) 0.1307(3) 0.60548(15) 0.0387(6) Uani 1 1 d . . . . .
C24 C 0.4463(3) 0.0246(3) 0.64411(17) 0.0467(6) Uani 1 1 d . . . . .
H24 H 0.5215 -0.0089 0.6242 0.056 Uiso 1 1 calc R U . . .
C25 C 0.4080(3) -0.0294(3) 0.71190(17) 0.0490(7) Uani 1 1 d . . . . .
H25 H 0.4582 -0.1014 0.7392 0.059 Uiso 1 1 calc R U . . .
C26 C 0.2975(3) 0.0185(3) 0.74194(16) 0.0484(7) Uani 1 1 d . . . . .
H26 H 0.2758 -0.0206 0.7896 0.058 Uiso 1 1 calc R U . . .
C27 C 0.2190(3) 0.1210(3) 0.70452(15) 0.0434(6) Uani 1 1 d . . . . .
H27 H 0.1429 0.1524 0.7243 0.052 Uiso 1 1 calc R U . . .
C27A C 0.2585(2) 0.1757(2) 0.63550(14) 0.0360(5) Uani 1 1 d . . . . .
N1 N 0.3650(2) 0.4203(2) 0.42328(11) 0.0323(4) Uani 1 1 d . . . . .
N1S N 0.78152(19) 0.1688(2) 0.48375(13) 0.0412(5) Uani 1 1 d . . . . .
N21 N 0.20635(19) 0.2792(2) 0.58535(12) 0.0353(5) Uani 1 1 d . . . . .
N23 N 0.38672(19) 0.2072(2) 0.53787(13) 0.0393(5) Uani 1 1 d . . . . .
O1S O 0.61799(17) 0.3164(2) 0.43603(12) 0.0494(5) Uani 1 1 d . . . . .
O4 O 0.03065(15) 0.64937(17) 0.38055(10) 0.0382(4) Uani 1 1 d . . . . .
H21 H 0.1198(18) 0.3188(19) 0.5896(11) 0.005(4) Uiso 1 1 d . . . . .
H1 H 0.435(3) 0.384(3) 0.4290(16) 0.038(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1S O1S 1.240(3) . ?
C1S N1S 1.336(3) . ?
C1S H1S 0.9500 . ?
C2 N1 1.351(3) . ?
C2 C3 1.374(3) . ?
C2 C22 1.463(3) . ?
C2S N1S 1.460(3) . ?
C2S H21S 0.9800 . ?
C2S H22S 0.9800 . ?
C2S H23S 0.9800 . ?
C3 C4 1.422(3) . ?
C3 H3 0.9500 . ?
C3S N1S 1.446(4) . ?
C3S H31S 0.9800 . ?
C3S H32S 0.9800 . ?
C3S H33S 0.9800 . ?
C4 O4 1.278(3) . ?
C4 C4A 1.464(3) . ?
C4A C8A 1.402(3) . ?
C4A C5 1.414(3) . ?
C5 C6 1.367(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.409(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(4) . ?
C7 H7 0.9500 . ?
C8 C8A 1.403(3) . ?
C8 H8 0.9500 . ?
C8A N1 1.384(3) . ?
C22 N23 1.306(3) . ?
C22 N21 1.377(3) . ?
C23A N23 1.397(3) . ?
C23A C24 1.399(4) . ?
C23A C27A 1.400(4) . ?
C24 C25 1.374(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.398(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.380(4) . ?
C26 H26 0.9500 . ?
C27 C27A 1.401(4) . ?
C27 H27 0.9500 . ?
C27A N21 1.375(3) . ?
N1 H1 0.80(3) . ?
N21 H21 0.990(19) . ?

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
O1S C1S N1S 124.8(3) . . ?
O1S C1S H1S 117.6 . . ?
N1S C1S H1S 117.6 . . ?
N1 C2 C3 121.1(2) . . ?
N1 C2 C22 116.59(19) . . ?
C3 C2 C22 122.3(2) . . ?
N1S C2S H21S 109.5 . . ?
N1S C2S H22S 109.5 . . ?
H21S C2S H22S 109.5 . . ?
N1S C2S H23S 109.5 . . ?
H21S C2S H23S 109.5 . . ?
H22S C2S H23S 109.5 . . ?
C2 C3 C4 122.1(2) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
N1S C3S H31S 109.5 . . ?
N1S C3S H32S 109.5 . . ?
H31S C3S H32S 109.5 . . ?
N1S C3S H33S 109.5 . . ?
H31S C3S H33S 109.5 . . ?
H32S C3S H33S 109.5 . . ?
O4 C4 C3 122.3(2) . . ?
O4 C4 C4A 122.3(2) . . ?
C3 C4 C4A 115.4(2) . . ?
C8A C4A C5 118.2(2) . . ?
C8A C4A C4 120.2(2) . . ?
C5 C4A C4 121.5(2) . . ?
C6 C5 C4A 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C4A C5 H5 119.4 . . ?
C5 C6 C7 120.0(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.1(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C8A 120.0(2) . . ?
C7 C8 H8 120.0 . . ?
C8A C8 H8 120.0 . . ?
N1 C8A C4A 119.8(2) . . ?
N1 C8A C8 119.7(2) . . ?
C4A C8A C8 120.5(2) . . ?
N23 C22 N21 114.0(2) . . ?
N23 C22 C2 124.1(2) . . ?
N21 C22 C2 121.9(2) . . ?
N23 C23A C24 130.4(2) . . ?
N23 C23A C27A 109.8(2) . . ?
C24 C23A C27A 119.8(2) . . ?
C25 C24 C23A 117.5(3) . . ?
C25 C24 H24 121.2 . . ?
C23A C24 H24 121.2 . . ?
C24 C25 C26 122.0(3) . . ?
C24 C25 H25 119.0 . . ?
C26 C25 H25 119.0 . . ?
C27 C26 C25 122.0(3) . . ?
C27 C26 H26 119.0 . . ?
C25 C26 H26 119.0 . . ?
C26 C27 C27A 115.7(3) . . ?
C26 C27 H27 122.1 . . ?
C27A C27 H27 122.1 . . ?
N21 C27A C23A 105.9(2) . . ?
N21 C27A C27 131.2(2) . . ?
C23A C27A C27 122.9(2) . . ?
C2 N1 C8A 121.3(2) . . ?
C2 N1 H1 127(2) . . ?
C8A N1 H1 111(2) . . ?
C1S N1S C3S 121.2(2) . . ?
C1S N1S C2S 120.9(2) . . ?
C3S N1S C2S 117.9(2) . . ?
C27A N21 C22 105.9(2) . . ?
C27A N21 H21 121.4(11) . . ?
C22 N21 H21 132.1(11) . . ?
C22 N23 C23A 104.4(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
N1 C2 C3 C4 -2.4(3) . . . . ?
C22 C2 C3 C4 176.9(2) . . . . ?
C2 C3 C4 O4 -176.8(2) . . . . ?
C2 C3 C4 C4A 2.5(3) . . . . ?
O4 C4 C4A C8A 178.0(2) . . . . ?
C3 C4 C4A C8A -1.4(3) . . . . ?
O4 C4 C4A C5 -1.0(3) . . . . ?
C3 C4 C4A C5 179.7(2) . . . . ?
C8A C4A C5 C6 0.1(4) . . . . ?
C4 C4A C5 C6 179.1(2) . . . . ?
C4A C5 C6 C7 -0.5(4) . . . . ?
C5 C6 C7 C8 0.4(4) . . . . ?
C6 C7 C8 C8A 0.0(4) . . . . ?
C5 C4A C8A N1 179.1(2) . . . . ?
C4 C4A C8A N1 0.1(3) . . . . ?
C5 C4A C8A C8 0.4(3) . . . . ?
C4 C4A C8A C8 -178.7(2) . . . . ?
C7 C8 C8A N1 -179.2(2) . . . . ?
C7 C8 C8A C4A -0.4(4) . . . . ?
N1 C2 C22 N23 -11.2(3) . . . . ?
C3 C2 C22 N23 169.4(2) . . . . ?
N1 C2 C22 N21 167.9(2) . . . . ?
C3 C2 C22 N21 -11.5(3) . . . . ?
N23 C23A C24 C25 177.9(2) . . . . ?
C27A C23A C24 C25 -1.3(4) . . . . ?
C23A C24 C25 C26 0.1(4) . . . . ?
C24 C25 C26 C27 1.2(4) . . . . ?
C25 C26 C27 C27A -1.2(4) . . . . ?
N23 C23A C27A N21 0.6(3) . . . . ?
C24 C23A C27A N21 179.9(2) . . . . ?
N23 C23A C27A C27 -178.1(2) . . . . ?
C24 C23A C27A C27 1.2(4) . . . . ?
C26 C27 C27A N21 -178.2(2) . . . . ?
C26 C27 C27A C23A 0.0(4) . . . . ?
C3 C2 N1 C8A 1.0(3) . . . . ?
C22 C2 N1 C8A -178.4(2) . . . . ?
C4A C8A N1 C2 0.1(3) . . . . ?
C8 C8A N1 C2 178.9(2) . . . . ?
O1S C1S N1S C3S -2.1(4) . . . . ?
O1S C1S N1S C2S 179.5(2) . . . . ?
C23A C27A N21 C22 -0.9(2) . . . . ?
C27 C27A N21 C22 177.5(3) . . . . ?
N23 C22 N21 C27A 1.0(3) . . . . ?
C2 C22 N21 C27A -178.2(2) . . . . ?
N21 C22 N23 C23A -0.7(3) . . . . ?
C2 C22 N23 C23A 178.5(2) . . . . ?
C24 C23A N23 C22 -179.2(3) . . . . ?
C27A C23A N23 C22 0.0(3) . . . . ?

_refine_diff_density_max         0.480
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.054


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dimethylformamide'
