# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_BU_VANTHANA_MQFAH_02122021_0m
_database_code_depnum_ccdc_archive 'CCDC 2241799'
loop_
_audit_author_name
_audit_author_address
'ELANCHERAN RAMAKRISHNAN'
;Department of Chemistry, Annamalai University
India
;
_audit_update_record             
;
2023-02-14 deposited with the CCDC.	2023-05-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 N4 O4'
_chemical_formula_weight         314.30

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

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

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

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

_cell_length_a                   10.1696(15)
_cell_length_b                   10.2024(16)
_cell_length_c                   14.523(2)
_cell_angle_alpha                78.333(5)
_cell_angle_beta                 79.157(5)
_cell_angle_gamma                86.414(5)
_cell_volume                     1448.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44289
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.039
_diffrn_reflns_theta_max         30.109
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             8433
_reflns_number_gt                5867
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1125P)²+0.5769P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8433
_refine_ls_number_parameters     417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0761
_refine_ls_wR_factor_ref         0.2400
_refine_ls_wR_factor_gt          0.2132
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8367(3) 0.7527(3) 0.05932(14) 0.0970(7) Uani 1 1 d . . . . .
O2 O 0.7353(2) 0.5853(2) 0.15323(14) 0.0931(7) Uani 1 1 d . . . . .
O3 O 0.9646(2) 0.75057(19) 0.69158(13) 0.0857(6) Uani 1 1 d . . . . .
O4 O 0.81578(16) 0.44227(15) 0.80812(11) 0.0583(4) Uani 1 1 d . . . . .
O5 O 0.2580(3) -0.0893(3) 0.94864(18) 0.1188(9) Uani 1 1 d . . . . .
O6 O 0.1591(3) -0.1743(3) 0.85705(18) 0.1168(9) Uani 1 1 d . . . . .
O7 O 0.5336(3) 0.3745(2) 0.30986(15) 0.0999(8) Uani 1 1 d . . . . .
O8 O 0.36715(17) 0.18906(17) 0.18758(12) 0.0671(4) Uani 1 1 d . . . . .
N1 N 0.8109(2) 0.6798(2) 0.13791(14) 0.0676(5) Uani 1 1 d . . . . .
N2 N 0.74155(19) 0.53848(19) 0.33662(13) 0.0591(5) Uani 1 1 d . . . . .
H2A H 0.717666 0.502566 0.293822 0.071 Uiso 1 1 calc R U . . .
N3 N 0.90716(16) 0.65763(16) 0.54118(12) 0.0479(4) Uani 1 1 d . . . . .
N4 N 0.87628(18) 0.59181(17) 0.63445(12) 0.0525(4) Uani 1 1 d . . . . .
H4 H 0.834231 0.517829 0.648329 0.063 Uiso 1 1 calc R U . . .
N5 N 0.2391(3) -0.0965(3) 0.86896(19) 0.0863(7) Uani 1 1 d . . . . .
N6 N 0.2122(2) -0.0930(2) 0.67028(16) 0.0734(6) Uani 1 1 d . . . . .
H6 H 0.146893 -0.128914 0.712716 0.088 Uiso 1 1 calc R U . . .
N7 N 0.41701(18) 0.18546(17) 0.45682(13) 0.0529(4) Uani 1 1 d . . . . .
N8 N 0.39973(18) 0.19619(18) 0.36444(13) 0.0554(4) Uani 1 1 d . . . . .
H8 H 0.347013 0.143235 0.350669 0.066 Uiso 1 1 calc R U . . .
C1 C 0.8705(2) 0.7072(2) 0.21453(15) 0.0528(4) Uani 1 1 d . . . . .
C2 C 0.9623(2) 0.8097(2) 0.19000(16) 0.0566(5) Uani 1 1 d . . . . .
H2 H 0.982571 0.854272 0.126737 0.068 Uiso 1 1 calc R U . . .
C3 C 1.0235(2) 0.8465(2) 0.25729(16) 0.0541(5) Uani 1 1 d . . . . .
C4 C 1.1224(3) 0.9575(3) 0.2307(2) 0.0742(7) Uani 1 1 d . . . . .
H4A H 1.192673 0.935291 0.267438 0.111 Uiso 1 1 calc R U . . .
H4B H 1.077675 1.039197 0.243851 0.111 Uiso 1 1 calc R U . . .
H4C H 1.159829 0.968947 0.163870 0.111 Uiso 1 1 calc R U . . .
C5 C 0.9879(2) 0.77758(19) 0.35134(15) 0.0503(4) Uani 1 1 d . . . . .
H5 H 1.028558 0.800391 0.397962 0.060 Uiso 1 1 calc R U . . .
C6 C 0.89496(18) 0.67688(18) 0.37875(13) 0.0444(4) Uani 1 1 d . . . . .
C7 C 0.83236(19) 0.63693(19) 0.30909(14) 0.0469(4) Uani 1 1 d . . . . .
C8 C 0.6852(4) 0.4934(4) 0.4334(2) 0.1167(15) Uani 1 1 d . . . . .
H8A H 0.654581 0.403155 0.440379 0.140 Uiso 1 1 calc R U . . .
H8AB H 0.606903 0.549406 0.449105 0.140 Uiso 1 1 calc R U . . .
C9 C 0.7691(3) 0.4920(3) 0.50167(17) 0.0668(6) Uani 1 1 d . . . . .
H9A H 0.824055 0.410541 0.505478 0.080 Uiso 1 1 calc R U . . .
H9AB H 0.713283 0.490144 0.563896 0.080 Uiso 1 1 calc R U . . .
C10 C 0.85887(19) 0.60976(18) 0.47922(14) 0.0462(4) Uani 1 1 d . . . . .
C11 C 0.9123(2) 0.6438(2) 0.70470(15) 0.0522(4) Uani 1 1 d . . . . .
C12 C 0.8796(2) 0.5592(2) 0.79977(14) 0.0522(4) Uani 1 1 d . . . . .
C13 C 0.9019(3) 0.5733(3) 0.88505(17) 0.0731(7) Uani 1 1 d . . . . .
H13 H 0.943189 0.644493 0.898221 0.088 Uiso 1 1 calc R U . . .
C14 C 0.8504(3) 0.4588(3) 0.95120(18) 0.0763(7) Uani 1 1 d . . . . .
H14 H 0.851541 0.439894 1.016439 0.092 Uiso 1 1 calc R U . . .
C15 C 0.8003(3) 0.3838(3) 0.90274(17) 0.0679(6) Uani 1 1 d . . . . .
H15 H 0.759972 0.302116 0.929381 0.082 Uiso 1 1 calc R U . . .
C16 C 0.3145(3) -0.0092(2) 0.78664(18) 0.0656(6) Uani 1 1 d . . . . .
C17 C 0.4027(3) 0.0757(3) 0.80567(18) 0.0674(6) Uani 1 1 d . . . . .
H17 H 0.412195 0.072329 0.868571 0.081 Uiso 1 1 calc R U . . .
C18 C 0.4766(2) 0.1650(2) 0.73364(17) 0.0604(5) Uani 1 1 d . . . . .
C19 C 0.5691(3) 0.2622(3) 0.7537(2) 0.0791(7) Uani 1 1 d . . . . .
H19A H 0.652993 0.262436 0.710344 0.119 Uiso 1 1 calc R U . . .
H19B H 0.584060 0.235450 0.818205 0.119 Uiso 1 1 calc R U . . .
H19C H 0.528879 0.350521 0.745116 0.119 Uiso 1 1 calc R U . . .
C20 C 0.4589(2) 0.1655(2) 0.64122(16) 0.0539(5) Uani 1 1 d . . . . .
H20 H 0.508282 0.224735 0.591442 0.065 Uiso 1 1 calc R U . . .
C21 C 0.3716(2) 0.08237(19) 0.61886(15) 0.0506(4) Uani 1 1 d . . . . .
C22 C 0.2958(2) -0.0118(2) 0.69324(17) 0.0575(5) Uani 1 1 d . . . . .
C23 C 0.2317(4) -0.1187(3) 0.5778(2) 0.1005(11) Uani 1 1 d . . . . .
H23A H 0.153998 -0.163749 0.570644 0.121 Uiso 1 1 calc R U . . .
H23B H 0.308540 -0.179138 0.569155 0.121 Uiso 1 1 calc R U . . .
C24 C 0.2536(3) 0.0034(3) 0.5015(2) 0.0695(6) Uani 1 1 d . . . . .
H24A H 0.168822 0.051433 0.497433 0.083 Uiso 1 1 calc R U . . .
H24B H 0.286806 -0.022701 0.440514 0.083 Uiso 1 1 calc R U . . .
C25 C 0.3513(2) 0.09400(19) 0.52038(16) 0.0513(4) Uani 1 1 d . . . . .
C26 C 0.4660(2) 0.2907(2) 0.29456(16) 0.0574(5) Uani 1 1 d . . . . .
C27 C 0.4494(2) 0.2836(2) 0.19848(16) 0.0563(5) Uani 1 1 d . . . . .
C28 C 0.5035(3) 0.3542(3) 0.11255(19) 0.0751(7) Uani 1 1 d . . . . .
H28 H 0.563891 0.423006 0.100450 0.090 Uiso 1 1 calc R U . . .
C29 C 0.4506(3) 0.3033(3) 0.0446(2) 0.0824(8) Uani 1 1 d . . . . .
H29 H 0.468363 0.332946 -0.021290 0.099 Uiso 1 1 calc R U . . .
C30 C 0.3705(3) 0.2050(3) 0.0923(2) 0.0817(8) Uani 1 1 d . . . . .
H30 H 0.322969 0.153862 0.064094 0.098 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
O1 N1 1.222(3) . ?
O2 N1 1.229(3) . ?
O3 C11 1.207(2) . ?
O4 C15 1.367(3) . ?
O4 C12 1.367(2) . ?
O5 N5 1.225(4) . ?
O6 N5 1.229(4) . ?
O7 C26 1.209(3) . ?
O8 C30 1.355(3) . ?
O8 C27 1.367(3) . ?
N1 C1 1.444(3) . ?
N2 C7 1.355(3) . ?
N2 C8 1.408(4) . ?
N2 H2A 0.8600 . ?
N3 C10 1.290(2) . ?
N3 N4 1.372(2) . ?
N4 C11 1.356(3) . ?
N4 H4 0.8600 . ?
N5 C16 1.456(3) . ?
N6 C22 1.352(3) . ?
N6 C23 1.396(4) . ?
N6 H6 0.8600 . ?
N7 C25 1.291(3) . ?
N7 N8 1.367(3) . ?
N8 C26 1.357(3) . ?
N8 H8 0.8600 . ?
C1 C2 1.392(3) . ?
C1 C7 1.409(3) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C5 1.396(3) . ?
C3 C4 1.504(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.427(3) . ?
C6 C10 1.469(3) . ?
C8 C9 1.423(4) . ?
C8 H8A 0.9700 . ?
C8 H8AB 0.9700 . ?
C9 C10 1.500(3) . ?
C9 H9A 0.9700 . ?
C9 H9AB 0.9700 . ?
C11 C12 1.464(3) . ?
C12 C13 1.337(3) . ?
C13 C14 1.413(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.320(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.386(4) . ?
C16 C22 1.410(4) . ?
C17 C18 1.376(3) . ?
C17 H17 0.9300 . ?
C18 C20 1.387(3) . ?
C18 C19 1.513(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.388(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.430(3) . ?
C21 C25 1.464(3) . ?
C23 C24 1.488(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.496(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C26 C27 1.453(3) . ?
C27 C28 1.344(3) . ?
C28 C29 1.405(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.326(4) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?

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
C15 O4 C12 105.49(18) . . ?
C30 O8 C27 105.85(19) . . ?
O1 N1 O2 121.8(2) . . ?
O1 N1 C1 118.5(2) . . ?
O2 N1 C1 119.7(2) . . ?
C7 N2 C8 121.81(19) . . ?
C7 N2 H2A 119.1 . . ?
C8 N2 H2A 119.1 . . ?
C10 N3 N4 116.52(16) . . ?
C11 N4 N3 119.79(16) . . ?
C11 N4 H4 120.1 . . ?
N3 N4 H4 120.1 . . ?
O5 N5 O6 122.1(3) . . ?
O5 N5 C16 118.1(3) . . ?
O6 N5 C16 119.8(3) . . ?
C22 N6 C23 120.1(2) . . ?
C22 N6 H6 120.0 . . ?
C23 N6 H6 120.0 . . ?
C25 N7 N8 117.15(18) . . ?
C26 N8 N7 119.80(17) . . ?
C26 N8 H8 120.1 . . ?
N7 N8 H8 120.1 . . ?
C2 C1 C7 122.68(19) . . ?
C2 C1 N1 116.2(2) . . ?
C7 C1 N1 121.05(19) . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C5 116.90(19) . . ?
C2 C3 C4 121.3(2) . . ?
C5 C3 C4 121.7(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C3 123.31(19) . . ?
C6 C5 H5 118.3 . . ?
C3 C5 H5 118.3 . . ?
C5 C6 C7 120.10(18) . . ?
C5 C6 C10 121.04(17) . . ?
C7 C6 C10 118.86(16) . . ?
N2 C7 C1 124.75(18) . . ?
N2 C7 C6 119.65(18) . . ?
C1 C7 C6 115.59(18) . . ?
N2 C8 C9 117.0(3) . . ?
N2 C8 H8A 108.0 . . ?
C9 C8 H8A 108.0 . . ?
N2 C8 H8AB 108.0 . . ?
C9 C8 H8AB 108.0 . . ?
H8A C8 H8AB 107.3 . . ?
C8 C9 C10 113.8(2) . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9AB 108.8 . . ?
C10 C9 H9AB 108.8 . . ?
H9A C9 H9AB 107.7 . . ?
N3 C10 C6 116.94(17) . . ?
N3 C10 C9 125.28(19) . . ?
C6 C10 C9 117.78(17) . . ?
O3 C11 N4 123.9(2) . . ?
O3 C11 C12 122.29(19) . . ?
N4 C11 C12 113.76(17) . . ?
C13 C12 O4 110.3(2) . . ?
C13 C12 C11 131.7(2) . . ?
O4 C12 C11 118.08(17) . . ?
C12 C13 C14 106.5(2) . . ?
C12 C13 H13 126.8 . . ?
C14 C13 H13 126.8 . . ?
C15 C14 C13 106.9(2) . . ?
C15 C14 H14 126.6 . . ?
C13 C14 H14 126.6 . . ?
C14 C15 O4 110.9(2) . . ?
C14 C15 H15 124.6 . . ?
O4 C15 H15 124.6 . . ?
C17 C16 C22 122.8(2) . . ?
C17 C16 N5 116.5(3) . . ?
C22 C16 N5 120.7(3) . . ?
C18 C17 C16 121.5(2) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C20 116.8(2) . . ?
C17 C18 C19 122.1(2) . . ?
C20 C18 C19 121.1(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 C21 123.6(2) . . ?
C18 C20 H20 118.2 . . ?
C21 C20 H20 118.2 . . ?
C20 C21 C22 119.8(2) . . ?
C20 C21 C25 120.82(18) . . ?
C22 C21 C25 119.3(2) . . ?
N6 C22 C16 125.4(2) . . ?
N6 C22 C21 119.2(2) . . ?
C16 C22 C21 115.4(2) . . ?
N6 C23 C24 113.9(3) . . ?
N6 C23 H23A 108.8 . . ?
C24 C23 H23A 108.8 . . ?
N6 C23 H23B 108.8 . . ?
C24 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 C25 111.8(2) . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24B 109.3 . . ?
C25 C24 H24B 109.3 . . ?
H24A C24 H24B 107.9 . . ?
N7 C25 C21 116.72(18) . . ?
N7 C25 C24 125.1(2) . . ?
C21 C25 C24 118.12(19) . . ?
O7 C26 N8 123.5(2) . . ?
O7 C26 C27 122.0(2) . . ?
N8 C26 C27 114.50(18) . . ?
C28 C27 O8 110.0(2) . . ?
C28 C27 C26 131.6(2) . . ?
O8 C27 C26 118.40(19) . . ?
C27 C28 C29 106.3(2) . . ?
C27 C28 H28 126.8 . . ?
C29 C28 H28 126.8 . . ?
C30 C29 C28 107.0(2) . . ?
C30 C29 H29 126.5 . . ?
C28 C29 H29 126.5 . . ?
C29 C30 O8 110.8(2) . . ?
C29 C30 H30 124.6 . . ?
O8 C30 H30 124.6 . . ?

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
C10 N3 N4 C11 -173.50(18) . . . . ?
C25 N7 N8 C26 179.88(19) . . . . ?
O1 N1 C1 C2 -5.0(3) . . . . ?
O2 N1 C1 C2 175.6(2) . . . . ?
O1 N1 C1 C7 172.4(2) . . . . ?
O2 N1 C1 C7 -7.0(3) . . . . ?
C7 C1 C2 C3 1.4(3) . . . . ?
N1 C1 C2 C3 178.8(2) . . . . ?
C1 C2 C3 C5 -0.9(3) . . . . ?
C1 C2 C3 C4 -179.8(2) . . . . ?
C2 C3 C5 C6 -0.4(3) . . . . ?
C4 C3 C5 C6 178.5(2) . . . . ?
C3 C5 C6 C7 1.3(3) . . . . ?
C3 C5 C6 C10 -178.55(19) . . . . ?
C8 N2 C7 C1 -165.3(3) . . . . ?
C8 N2 C7 C6 13.8(4) . . . . ?
C2 C1 C7 N2 178.6(2) . . . . ?
N1 C1 C7 N2 1.3(3) . . . . ?
C2 C1 C7 C6 -0.5(3) . . . . ?
N1 C1 C7 C6 -177.74(18) . . . . ?
C5 C6 C7 N2 -179.93(18) . . . . ?
C10 C6 C7 N2 -0.1(3) . . . . ?
C5 C6 C7 C1 -0.8(3) . . . . ?
C10 C6 C7 C1 179.05(17) . . . . ?
C7 N2 C8 C9 -34.5(5) . . . . ?
N2 C8 C9 C10 38.7(5) . . . . ?
N4 N3 C10 C6 -178.06(16) . . . . ?
N4 N3 C10 C9 2.1(3) . . . . ?
C5 C6 C10 N3 6.7(3) . . . . ?
C7 C6 C10 N3 -173.19(17) . . . . ?
C5 C6 C10 C9 -173.5(2) . . . . ?
C7 C6 C10 C9 6.7(3) . . . . ?
C8 C9 C10 N3 154.2(3) . . . . ?
C8 C9 C10 C6 -25.6(4) . . . . ?
N3 N4 C11 O3 4.3(3) . . . . ?
N3 N4 C11 C12 -176.71(17) . . . . ?
C15 O4 C12 C13 -0.4(3) . . . . ?
C15 O4 C12 C11 179.0(2) . . . . ?
O3 C11 C12 C13 -3.2(4) . . . . ?
N4 C11 C12 C13 177.9(3) . . . . ?
O3 C11 C12 O4 177.6(2) . . . . ?
N4 C11 C12 O4 -1.4(3) . . . . ?
O4 C12 C13 C14 0.4(3) . . . . ?
C11 C12 C13 C14 -178.9(2) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 O4 0.0(3) . . . . ?
C12 O4 C15 C14 0.3(3) . . . . ?
O5 N5 C16 C17 0.1(4) . . . . ?
O6 N5 C16 C17 -180.0(3) . . . . ?
O5 N5 C16 C22 -179.2(3) . . . . ?
O6 N5 C16 C22 0.7(4) . . . . ?
C22 C16 C17 C18 1.0(4) . . . . ?
N5 C16 C17 C18 -178.3(2) . . . . ?
C16 C17 C18 C20 -0.3(3) . . . . ?
C16 C17 C18 C19 177.5(2) . . . . ?
C17 C18 C20 C21 0.3(3) . . . . ?
C19 C18 C20 C21 -177.4(2) . . . . ?
C18 C20 C21 C22 -1.1(3) . . . . ?
C18 C20 C21 C25 175.99(19) . . . . ?
C23 N6 C22 C16 -159.3(3) . . . . ?
C23 N6 C22 C21 21.8(4) . . . . ?
C17 C16 C22 N6 179.4(2) . . . . ?
N5 C16 C22 N6 -1.3(4) . . . . ?
C17 C16 C22 C21 -1.7(3) . . . . ?
N5 C16 C22 C21 177.6(2) . . . . ?
C20 C21 C22 N6 -179.3(2) . . . . ?
C25 C21 C22 N6 3.5(3) . . . . ?
C20 C21 C22 C16 1.7(3) . . . . ?
C25 C21 C22 C16 -175.46(18) . . . . ?
C22 N6 C23 C24 -47.6(4) . . . . ?
N6 C23 C24 C25 45.7(4) . . . . ?
N8 N7 C25 C21 179.35(17) . . . . ?
N8 N7 C25 C24 -2.9(3) . . . . ?
C20 C21 C25 N7 -0.7(3) . . . . ?
C22 C21 C25 N7 176.39(18) . . . . ?
C20 C21 C25 C24 -178.7(2) . . . . ?
C22 C21 C25 C24 -1.6(3) . . . . ?
C23 C24 C25 N7 159.9(2) . . . . ?
C23 C24 C25 C21 -22.4(3) . . . . ?
N7 N8 C26 O7 -5.7(4) . . . . ?
N7 N8 C26 C27 174.34(18) . . . . ?
C30 O8 C27 C28 -1.0(3) . . . . ?
C30 O8 C27 C26 -180.0(2) . . . . ?
O7 C26 C27 C28 3.8(5) . . . . ?
N8 C26 C27 C28 -176.3(3) . . . . ?
O7 C26 C27 O8 -177.5(2) . . . . ?
N8 C26 C27 O8 2.5(3) . . . . ?
O8 C27 C28 C29 1.2(3) . . . . ?
C26 C27 C28 C29 -180.0(3) . . . . ?
C27 C28 C29 C30 -1.0(4) . . . . ?
C28 C29 C30 O8 0.4(4) . . . . ?
C27 O8 C30 C29 0.3(3) . . . . ?

_refine_diff_density_max         0.997
_refine_diff_density_min         -0.768
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_qtah
_database_code_depnum_ccdc_archive 'CCDC 2241815'
loop_
_audit_author_name
_audit_author_address
'Jan Grzegorz Malecki'
;University of Silesia in Katowice , Institute of Chemistry
Poland
;
_audit_update_record             
;
2023-02-14 deposited with the CCDC.	2023-05-17 downloaded from the CCDC.
;
_audit_creation_date             2021-12-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 N4 O3 S'
_chemical_formula_sum            'C14 H12 N4 O3 S'
_chemical_formula_weight         316.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H13 N4 O3 S1'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
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                   9.0301(4)
_cell_length_b                   13.7515(7)
_cell_length_c                   11.0994(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.892(5)
_cell_angle_gamma                90
_cell_volume                     1373.29(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2960
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.9630
_cell_measurement_theta_min      4.0930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7169
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.343
_diffrn_reflns_theta_min         3.685
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  16.00   1.00   12.34    --   10.22  77.00  30.00   26
  2  ω     -7.00  60.00   1.00   12.34    --   10.22  38.00-180.00   67
  3  ω    -15.00  11.00   1.00   12.34    --  -11.31 -19.00 -90.00   26
  4  ω    -44.00  33.00   1.00   12.34    --  -11.31  77.00-120.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0049170000
_diffrn_orient_matrix_UB_12      0.0335511000
_diffrn_orient_matrix_UB_13      -0.0480218000
_diffrn_orient_matrix_UB_21      0.0057324000
_diffrn_orient_matrix_UB_22      0.0388762000
_diffrn_orient_matrix_UB_23      0.0421423000
_diffrn_orient_matrix_UB_31      0.0784794000
_diffrn_orient_matrix_UB_32      -0.0049375000
_diffrn_orient_matrix_UB_33      0.0054433000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2338
_reflns_number_total             3238
_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       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0510P)²+0.3820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1203
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.02614(5) 0.64978(4) 0.42425(5) 0.05066(18) Uani 1 1 d . . . . .
O1 O 0.15106(13) 0.92360(10) 0.48613(14) 0.0523(4) Uani 1 1 d . . . . .
O2 O -0.84984(18) 0.82420(14) 0.14426(19) 0.0825(6) Uani 1 1 d . . . . .
O3 O -0.88710(15) 0.67288(12) 0.10887(14) 0.0606(4) Uani 1 1 d . . . . .
N1 N -0.07550(16) 0.87662(12) 0.41628(15) 0.0404(4) Uani 1 1 d . . . . .
H1 H -0.102(2) 0.9331(17) 0.426(2) 0.054(7) Uiso 1 1 d . . . . .
N2 N -0.17828(14) 0.80565(11) 0.38254(13) 0.0364(3) Uani 1 1 d . . . . .
N3 N -0.60128(19) 0.88482(12) 0.25585(17) 0.0472(4) Uani 1 1 d . . . . .
H3 H -0.682(3) 0.8956(19) 0.240(2) 0.067(8) Uiso 1 1 d . . . . .
N4 N -0.80754(17) 0.73921(13) 0.14973(15) 0.0474(4) Uani 1 1 d . . . . .
C1 C 0.06671(19) 0.85549(13) 0.45703(17) 0.0376(4) Uani 1 1 d . . . . .
C2 C -0.30929(18) 0.83495(13) 0.34434(16) 0.0350(4) Uani 1 1 d . . . . .
C3 C -0.3570(2) 0.93896(14) 0.3309(2) 0.0499(5) Uani 1 1 d . . . . .
H3A H -0.303552 0.977613 0.393519 0.060 Uiso 1 1 calc R U . . .
H3B H -0.331887 0.963289 0.253190 0.060 Uiso 1 1 calc R U . . .
C4 C -0.5205(2) 0.94991(15) 0.3398(2) 0.0539(6) Uani 1 1 d . . . . .
H4A H -0.543914 0.935276 0.421561 0.065 Uiso 1 1 calc R U . . .
H4B H -0.549964 1.016499 0.321711 0.065 Uiso 1 1 calc R U . . .
C5 C -0.56410(18) 0.79006(13) 0.25465(15) 0.0339(4) Uani 1 1 d . . . . .
C6 C -0.66028(18) 0.71604(14) 0.20526(16) 0.0375(4) Uani 1 1 d . . . . .
C7 C -0.6208(2) 0.61886(15) 0.21060(18) 0.0442(5) Uani 1 1 d . . . . .
H7 H -0.686613 0.572044 0.177509 0.053 Uiso 1 1 calc R U . . .
C8 C -0.4854(2) 0.59140(14) 0.2644(2) 0.0475(5) Uani 1 1 d . . . . .
H8 H -0.459887 0.525951 0.270642 0.057 Uiso 1 1 calc R U . . .
C9 C -0.3867(2) 0.66206(14) 0.30950(19) 0.0435(5) Uani 1 1 d . . . . .
H9 H -0.294060 0.642927 0.344464 0.052 Uiso 1 1 calc R U . . .
C10 C -0.42068(18) 0.75997(13) 0.30454(16) 0.0338(4) Uani 1 1 d . . . . .
C11 C 0.12061(18) 0.75459(13) 0.46684(16) 0.0364(4) Uani 1 1 d . . . . .
C12 C 0.2631(2) 0.73328(15) 0.51727(19) 0.0451(5) Uani 1 1 d . . . . .
H12 H 0.331473 0.779979 0.546501 0.054 Uiso 1 1 calc R U . . .
C13 C 0.2916(2) 0.63257(17) 0.5189(2) 0.0528(5) Uani 1 1 d . . . . .
H13 H 0.381480 0.605403 0.549207 0.063 Uiso 1 1 calc R U . . .
C14 C 0.1749(2) 0.57966(16) 0.4718(2) 0.0573(6) Uani 1 1 d . . . . .
H14 H 0.175671 0.512197 0.465983 0.069 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
S1 C11 1.7204(18) . ?
S1 C14 1.700(2) . ?
O1 C1 1.233(2) . ?
O2 N4 1.230(2) . ?
O3 N4 1.224(2) . ?
N1 H1 0.82(2) . ?
N1 N2 1.377(2) . ?
N1 C1 1.356(2) . ?
N2 C2 1.287(2) . ?
N3 H3 0.75(2) . ?
N3 C4 1.444(2) . ?
N3 C5 1.346(2) . ?
N4 C6 1.453(2) . ?
C1 C11 1.471(2) . ?
C2 C3 1.498(2) . ?
C2 C10 1.481(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.496(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.418(2) . ?
C5 C10 1.426(2) . ?
C6 C7 1.383(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.368(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(2) . ?
C11 C12 1.390(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.409(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.349(3) . ?
C14 H14 0.9300 . ?

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
C14 S1 C11 91.70(10) . . ?
N2 N1 H1 120.3(15) . . ?
C1 N1 H1 116.2(15) . . ?
C1 N1 N2 122.42(16) . . ?
C2 N2 N1 116.56(15) . . ?
C4 N3 H3 117(2) . . ?
C5 N3 H3 115(2) . . ?
C5 N3 C4 119.57(16) . . ?
O2 N4 C6 119.92(16) . . ?
O3 N4 O2 121.33(17) . . ?
O3 N4 C6 118.75(18) . . ?
O1 C1 N1 118.10(17) . . ?
O1 C1 C11 120.26(16) . . ?
N1 C1 C11 121.64(15) . . ?
N2 C2 C3 125.47(16) . . ?
N2 C2 C10 117.53(16) . . ?
C10 C2 C3 116.93(14) . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.51(16) . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
N3 C4 C3 110.01(17) . . ?
N3 C4 H4A 109.7 . . ?
N3 C4 H4B 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N3 C5 C6 123.63(16) . . ?
N3 C5 C10 119.74(16) . . ?
C6 C5 C10 116.63(16) . . ?
C5 C6 N4 121.01(17) . . ?
C7 C6 N4 116.95(16) . . ?
C7 C6 C5 122.02(16) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.19(17) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.4 . . ?
C7 C8 C9 119.24(18) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 H9 118.8 . . ?
C10 C9 C8 122.48(17) . . ?
C10 C9 H9 118.8 . . ?
C5 C10 C2 119.02(15) . . ?
C9 C10 C2 121.60(15) . . ?
C9 C10 C5 119.31(16) . . ?
C1 C11 S1 128.06(13) . . ?
C12 C11 S1 110.75(14) . . ?
C12 C11 C1 121.17(16) . . ?
C11 C12 H12 124.0 . . ?
C11 C12 C13 111.99(18) . . ?
C13 C12 H12 124.0 . . ?
C12 C13 H13 123.5 . . ?
C14 C13 C12 112.92(19) . . ?
C14 C13 H13 123.5 . . ?
S1 C14 H14 123.7 . . ?
C13 C14 S1 112.63(17) . . ?
C13 C14 H14 123.7 . . ?

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
S1 C11 C12 C13 0.5(2) . . . . ?
O1 C1 C11 S1 -176.27(15) . . . . ?
O1 C1 C11 C12 4.9(3) . . . . ?
O2 N4 C6 C5 0.6(3) . . . . ?
O2 N4 C6 C7 178.74(19) . . . . ?
O3 N4 C6 C5 -179.59(17) . . . . ?
O3 N4 C6 C7 -1.4(3) . . . . ?
N1 N2 C2 C3 1.6(3) . . . . ?
N1 N2 C2 C10 178.46(15) . . . . ?
N1 C1 C11 S1 3.8(3) . . . . ?
N1 C1 C11 C12 -175.04(18) . . . . ?
N2 N1 C1 O1 -179.48(16) . . . . ?
N2 N1 C1 C11 0.5(3) . . . . ?
N2 C2 C3 C4 -154.14(19) . . . . ?
N2 C2 C10 C5 -176.13(16) . . . . ?
N2 C2 C10 C9 0.9(3) . . . . ?
N3 C5 C6 N4 1.1(3) . . . . ?
N3 C5 C6 C7 -176.96(18) . . . . ?
N3 C5 C10 C2 -6.8(3) . . . . ?
N3 C5 C10 C9 176.13(18) . . . . ?
N4 C6 C7 C8 -178.31(17) . . . . ?
C1 N1 N2 C2 -179.39(17) . . . . ?
C1 C11 C12 C13 179.48(17) . . . . ?
C2 C3 C4 N3 -52.9(3) . . . . ?
C3 C2 C10 C5 1.0(2) . . . . ?
C3 C2 C10 C9 177.97(18) . . . . ?
C4 N3 C5 C6 159.95(19) . . . . ?
C4 N3 C5 C10 -20.4(3) . . . . ?
C5 N3 C4 C3 50.9(3) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C6 C5 C10 C2 172.90(16) . . . . ?
C6 C5 C10 C9 -4.2(3) . . . . ?
C6 C7 C8 C9 -2.2(3) . . . . ?
C7 C8 C9 C10 1.3(3) . . . . ?
C8 C9 C10 C2 -175.01(18) . . . . ?
C8 C9 C10 C5 2.0(3) . . . . ?
C10 C2 C3 C4 29.0(3) . . . . ?
C10 C5 C6 N4 -178.58(16) . . . . ?
C10 C5 C6 C7 3.4(3) . . . . ?
C11 S1 C14 C13 0.39(18) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 S1 -0.2(3) . . . . ?
C14 S1 C11 C1 -179.40(18) . . . . ?
C14 S1 C11 C12 -0.50(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.562
_oxdiff_exptl_absorpt_empirical_full_min 0.780
