# Supplementary Information (SI) for Journal of Materials Chemistry B.
# This journal is © The Royal Society of Chemistry 2024

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2256566'
loop_
_audit_author_name
_audit_author_address
'Aziz Kalilur Rahiman'
;The New College
India
;
_audit_update_record             
;
2024-05-06 deposited with the CCDC.	2024-11-12 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         'C19 H22 N4 O5, C2 H6 O S'
_chemical_formula_sum            'C21 H28 N4 O6 S'
_chemical_formula_weight         464.53

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                   9.5427(8)
_cell_length_b                   18.3688(16)
_cell_length_c                   14.1766(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.890(3)
_cell_angle_gamma                90
_cell_volume                     2471.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    5458
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      30.47

_exptl_crystal_description       Solid
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.172
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48905
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.217
_diffrn_reflns_theta_max         27.129
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5458
_reflns_number_gt                4148
_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 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008)'
_computing_publication_material  
'WinGX (Farrugia, 2012), pubCIF (Westrip, 2010) and PLATON (Spek, 2009)'
_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)+(0.0757P)²+1.2472P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5458
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1717
_refine_ls_wR_factor_gt          0.1563
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1101(3) 0.18287(15) 0.18676(19) 0.0693(7) Uani 1 1 d . . . . .
H1 H 0.065119 0.144423 0.153434 0.083 Uiso 1 1 calc R U . . .
C1A C 0.0917(3) 0.35953(18) 1.02351(19) 0.0770(8) Uani 1 1 d . . . . .
H1A H 0.072739 0.359701 1.086565 0.092 Uiso 1 1 calc R U . . .
C2 C 0.2348(3) 0.20972(13) 0.16029(17) 0.0574(5) Uani 1 1 d . . . . .
C2A C 0.1652(3) 0.41667(15) 0.98922(17) 0.0673(6) Uani 1 1 d . . . . .
C3 C 0.3006(2) 0.26848(11) 0.21034(14) 0.0483(5) Uani 1 1 d . . . . .
C3A C 0.1963(3) 0.41626(13) 0.89462(16) 0.0568(5) Uani 1 1 d . . . . .
C4 C 0.2441(2) 0.29768(12) 0.28824(14) 0.0473(5) Uani 1 1 d . . . . .
C4A C 0.1482(2) 0.35925(13) 0.83602(16) 0.0538(5) Uani 1 1 d . . . . .
C5 C 0.3196(2) 0.35569(11) 0.34291(14) 0.0473(5) Uani 1 1 d . . . . .
H5 H 0.390128 0.381328 0.316693 0.057 Uiso 1 1 calc R U . . .
C5A C 0.1707(2) 0.35657(12) 0.73627(16) 0.0543(5) Uani 1 1 d . . . . .
H5A H 0.130158 0.319136 0.698657 0.065 Uiso 1 1 calc R U . . .
C6 C 0.3525(2) 0.44004(11) 0.56465(14) 0.0456(4) Uani 1 1 d . . . . .
C7 C 0.1171(2) 0.26935(14) 0.31394(17) 0.0594(6) Uani 1 1 d . . . . .
H7 H 0.076938 0.288661 0.365527 0.071 Uiso 1 1 calc R U . . .
C7A C 0.0462(3) 0.30259(18) 0.9662(2) 0.0804(8) Uani 1 1 d . . . . .
H7A H -0.002884 0.264283 0.990303 0.096 Uiso 1 1 calc R U . . .
C8 C 0.0519(3) 0.21316(16) 0.26304(19) 0.0714(7) Uani 1 1 d . . . . .
H8 H -0.032954 0.195112 0.280147 0.086 Uiso 1 1 calc R U . . .
C8A C 0.0730(3) 0.30210(16) 0.87333(19) 0.0719(7) Uani 1 1 d . . . . .
H8A H 0.041210 0.263507 0.834407 0.086 Uiso 1 1 calc R U . . .
C9 C 0.2501(4) 0.12743(19) 0.0299(2) 0.0975(11) Uani 1 1 d . . . . .
H9A H 0.157276 0.140196 0.000177 0.117 Uiso 1 1 calc R U . . .
H9B H 0.242027 0.083752 0.067440 0.117 Uiso 1 1 calc R U . . .
C9A C 0.1738(6) 0.4794(2) 1.1360(2) 0.1310(17) Uani 1 1 d . . . . .
H9AA H 0.071911 0.479401 1.134086 0.157 Uiso 1 1 calc R U . . .
H9BB H 0.209526 0.437209 1.171917 0.157 Uiso 1 1 calc R U . . .
C10 C 0.3483(5) 0.1149(3) -0.0434(4) 0.174(3) Uani 1 1 d . . . . .
H10A H 0.301568 0.087078 -0.094566 0.261 Uiso 1 1 calc R U . . .
H10B H 0.429478 0.088734 -0.015813 0.261 Uiso 1 1 calc R U . . .
H10C H 0.377370 0.160916 -0.066992 0.261 Uiso 1 1 calc R U . . .
C10A C 0.2279(8) 0.5426(3) 1.1801(3) 0.175(3) Uani 1 1 d . . . . .
10AA H 0.197298 0.584092 1.142191 0.262 Uiso 1 1 calc R U . . .
10AB H 0.328907 0.540487 1.186927 0.262 Uiso 1 1 calc R U . . .
10AC H 0.194624 0.546860 1.241494 0.262 Uiso 1 1 calc R U . . .
C11 C 0.7556(4) 0.34982(19) 0.1483(3) 0.0958(10) Uani 1 1 d . . . . .
H11A H 0.683639 0.354061 0.190581 0.144 Uiso 1 1 calc R U . . .
H11B H 0.797621 0.396621 0.140468 0.144 Uiso 1 1 calc R U . . .
H11C H 0.826394 0.316230 0.174190 0.144 Uiso 1 1 calc R U . . .
C12 C 0.5548(4) 0.38798(17) 0.0129(2) 0.0882(9) Uani 1 1 d . . . . .
H12A H 0.498828 0.378364 -0.045948 0.132 Uiso 1 1 calc R U . . .
H12B H 0.602794 0.433608 0.008759 0.132 Uiso 1 1 calc R U . . .
H12C H 0.494789 0.390220 0.063250 0.132 Uiso 1 1 calc R U . . .
N1 N 0.28971(19) 0.37149(9) 0.42595(12) 0.0489(4) Uani 1 1 d . . . . .
N1A N 0.24514(19) 0.40453(10) 0.69900(12) 0.0492(4) Uani 1 1 d . . . . .
N2 N 0.3656(2) 0.42675(10) 0.47184(12) 0.0523(4) Uani 1 1 d . . . . .
H2A H 0.421348 0.452870 0.441891 0.064(7) Uiso 1 1 calc R . . . .
N2A N 0.2598(2) 0.39651(10) 0.60411(12) 0.0524(4) Uani 1 1 d . . . . .
H2AA H 0.211203 0.364593 0.570546 0.063 Uiso 1 1 calc R U . . .
O1 O 0.42163(17) 0.48811(8) 0.60826(10) 0.0561(4) Uani 1 1 d . . . . .
O2 O 0.42266(18) 0.29618(9) 0.18431(11) 0.0605(4) Uani 1 1 d . . . . .
H2 H 0.448876 0.271639 0.141103 0.091 Uiso 1 1 calc R U . . .
O2A O 0.2718(3) 0.47228(10) 0.86333(13) 0.0795(6) Uani 1 1 d . . . . .
H2AB H 0.286232 0.464867 0.808119 0.119 Uiso 1 1 calc R U . . .
O3 O 0.3063(2) 0.18529(11) 0.08831(14) 0.0805(6) Uani 1 1 d . . . . .
O3A O 0.2139(3) 0.47522(12) 1.04089(14) 0.0953(7) Uani 1 1 d . . . . .
O4 O 0.5990(2) 0.25034(9) 0.05785(12) 0.0659(5) Uani 1 1 d . . . . .
S1 S 0.67980(7) 0.31752(4) 0.03646(5) 0.0695(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.375(3) . ?
C1 C8 1.382(4) . ?
C1 H1 0.9300 . ?
C1A C7A 1.368(4) . ?
C1A C2A 1.378(4) . ?
C1A H1A 0.9300 . ?
C2 O3 1.361(3) . ?
C2 C3 1.404(3) . ?
C2A O3A 1.356(3) . ?
C2A C3A 1.403(3) . ?
C3 O2 1.356(2) . ?
C3 C4 1.386(3) . ?
C3A O2A 1.357(3) . ?
C3A C4A 1.385(3) . ?
C4 C7 1.402(3) . ?
C4 C5 1.463(3) . ?
C4A C8A 1.405(3) . ?
C4A C5A 1.453(3) . ?
C5 N1 1.273(3) . ?
C5 H5 0.9300 . ?
C5A N1A 1.279(3) . ?
C5A H5A 0.9300 . ?
C6 O1 1.230(2) . ?
C6 N2A 1.355(3) . ?
C6 N2 1.357(3) . ?
C7 C8 1.371(4) . ?
C7 H7 0.9300 . ?
C7A C8A 1.366(4) . ?
C7A H7A 0.9300 . ?
C8 H8 0.9300 . ?
C8A H8A 0.9300 . ?
C9 O3 1.418(3) . ?
C9 C10 1.487(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9A C10A 1.393(6) . ?
C9A O3A 1.440(4) . ?
C9A H9AA 0.9700 . ?
C9A H9BB 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10A 10AA 0.9600 . ?
C10A 10AB 0.9600 . ?
C10A 10AC 0.9600 . ?
C11 S1 1.775(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 S1 1.769(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N1 N2 1.372(2) . ?
N1A N2A 1.375(2) . ?
N2 H2A 0.8600 . ?
N2A H2AA 0.8600 . ?
O2 H2 0.8200 . ?
O2A H2AB 0.8200 . ?
O4 S1 1.5024(18) . ?

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
C2 C1 C8 119.8(2) . . ?
C2 C1 H1 120.1 . . ?
C8 C1 H1 120.1 . . ?
C7A C1A C2A 121.0(2) . . ?
C7A C1A H1A 119.5 . . ?
C2A C1A H1A 119.5 . . ?
O3 C2 C1 126.9(2) . . ?
O3 C2 C3 113.54(19) . . ?
C1 C2 C3 119.5(2) . . ?
O3A C2A C1A 124.9(2) . . ?
O3A C2A C3A 115.2(2) . . ?
C1A C2A C3A 119.9(2) . . ?
O2 C3 C4 119.12(18) . . ?
O2 C3 C2 120.21(19) . . ?
C4 C3 C2 120.65(19) . . ?
O2A C3A C4A 122.1(2) . . ?
O2A C3A C2A 118.7(2) . . ?
C4A C3A C2A 119.2(2) . . ?
C3 C4 C7 118.8(2) . . ?
C3 C4 C5 119.60(18) . . ?
C7 C4 C5 121.6(2) . . ?
C3A C4A C8A 119.3(2) . . ?
C3A C4A C5A 122.4(2) . . ?
C8A C4A C5A 118.3(2) . . ?
N1 C5 C4 120.77(19) . . ?
N1 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
N1A C5A C4A 121.5(2) . . ?
N1A C5A H5A 119.2 . . ?
C4A C5A H5A 119.2 . . ?
O1 C6 N2A 123.73(18) . . ?
O1 C6 N2 121.21(18) . . ?
N2A C6 N2 115.06(18) . . ?
C8 C7 C4 120.0(2) . . ?
C8 C7 H7 120.0 . . ?
C4 C7 H7 120.0 . . ?
C8A C7A C1A 119.9(3) . . ?
C8A C7A H7A 120.1 . . ?
C1A C7A H7A 120.1 . . ?
C7 C8 C1 121.2(2) . . ?
C7 C8 H8 119.4 . . ?
C1 C8 H8 119.4 . . ?
C7A C8A C4A 120.7(3) . . ?
C7A C8A H8A 119.6 . . ?
C4A C8A H8A 119.6 . . ?
O3 C9 C10 107.2(3) . . ?
O3 C9 H9A 110.3 . . ?
C10 C9 H9A 110.3 . . ?
O3 C9 H9B 110.3 . . ?
C10 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
C10A C9A O3A 110.0(4) . . ?
C10A C9A H9AA 109.7 . . ?
O3A C9A H9AA 109.7 . . ?
C10A C9A H9BB 109.7 . . ?
O3A C9A H9BB 109.7 . . ?
H9AA C9A H9BB 108.2 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9A C10A 10AA 109.5 . . ?
C9A C10A 10AB 109.5 . . ?
10AA C10A 10AB 109.5 . . ?
C9A C10A 10AC 109.5 . . ?
10AA C10A 10AC 109.5 . . ?
10AB C10A 10AC 109.5 . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
S1 C12 H12A 109.5 . . ?
S1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
S1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 N1 N2 116.74(17) . . ?
C5A N1A N2A 116.54(18) . . ?
C6 N2 N1 119.75(17) . . ?
C6 N2 H2A 120.1 . . ?
N1 N2 H2A 120.1 . . ?
C6 N2A N1A 118.48(17) . . ?
C6 N2A H2AA 120.8 . . ?
N1A N2A H2AA 120.8 . . ?
C3 O2 H2 109.5 . . ?
C3A O2A H2AB 109.5 . . ?
C2 O3 C9 119.7(2) . . ?
C2A O3A C9A 116.0(3) . . ?
O4 S1 C12 106.79(14) . . ?
O4 S1 C11 105.35(14) . . ?
C12 S1 C11 97.40(17) . . ?

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
C8 C1 C2 O3 178.9(3) . . . . ?
C8 C1 C2 C3 -0.9(4) . . . . ?
C7A C1A C2A O3A 179.9(3) . . . . ?
C7A C1A C2A C3A -1.0(4) . . . . ?
O3 C2 C3 O2 1.0(3) . . . . ?
C1 C2 C3 O2 -179.1(2) . . . . ?
O3 C2 C3 C4 -177.3(2) . . . . ?
C1 C2 C3 C4 2.5(4) . . . . ?
O3A C2A C3A O2A 0.8(4) . . . . ?
C1A C2A C3A O2A -178.4(3) . . . . ?
O3A C2A C3A C4A -178.7(2) . . . . ?
C1A C2A C3A C4A 2.1(4) . . . . ?
O2 C3 C4 C7 179.2(2) . . . . ?
C2 C3 C4 C7 -2.5(3) . . . . ?
O2 C3 C4 C5 -2.3(3) . . . . ?
C2 C3 C4 C5 176.0(2) . . . . ?
O2A C3A C4A C8A 178.7(2) . . . . ?
C2A C3A C4A C8A -1.8(4) . . . . ?
O2A C3A C4A C5A -2.2(4) . . . . ?
C2A C3A C4A C5A 177.2(2) . . . . ?
C3 C4 C5 N1 -163.1(2) . . . . ?
C7 C4 C5 N1 15.3(3) . . . . ?
C3A C4A C5A N1A 5.0(4) . . . . ?
C8A C4A C5A N1A -175.9(2) . . . . ?
C3 C4 C7 C8 0.8(3) . . . . ?
C5 C4 C7 C8 -177.6(2) . . . . ?
C2A C1A C7A C8A -0.3(5) . . . . ?
C4 C7 C8 C1 0.8(4) . . . . ?
C2 C1 C8 C7 -0.7(4) . . . . ?
C1A C7A C8A C4A 0.6(5) . . . . ?
C3A C4A C8A C7A 0.5(4) . . . . ?
C5A C4A C8A C7A -178.6(3) . . . . ?
C4 C5 N1 N2 -179.86(18) . . . . ?
C4A C5A N1A N2A 179.8(2) . . . . ?
O1 C6 N2 N1 178.29(19) . . . . ?
N2A C6 N2 N1 -1.2(3) . . . . ?
C5 N1 N2 C6 -171.37(19) . . . . ?
O1 C6 N2A N1A -2.3(3) . . . . ?
N2 C6 N2A N1A 177.21(18) . . . . ?
C5A N1A N2A C6 -171.3(2) . . . . ?
C1 C2 O3 C9 2.0(5) . . . . ?
C3 C2 O3 C9 -178.2(3) . . . . ?
C10 C9 O3 C2 178.1(4) . . . . ?
C1A C2A O3A C9A -5.5(5) . . . . ?
C3A C2A O3A C9A 175.4(3) . . . . ?
C10A C9A O3A C2A -178.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O3 0.82 2.17 2.631(2) 115.5 . yes
O2 H2 O4 0.82 1.99 2.716(2) 147.8 . yes
N2 H2A O1 0.86 2.04 2.886(2) 169.8 3_666 yes
N2A H2AA N1 0.86 2.26 2.611(2) 104.7 . yes
N2A H2AA O4 0.86 2.37 3.139(3) 149.8 4_566 yes
O2A H2AB N1A 0.82 1.91 2.630(2) 145.9 . yes
C5A H5A O4 0.93 2.36 3.220(3) 153.2 4_566 yes
C8A H8A O2 0.93 2.55 3.422(3) 155.8 4_566 yes
C11 H11B O2A 0.96 2.50 3.281(4) 138.9 3_666 yes
C12 H12B O3A 0.96 2.57 3.481(4) 158.1 3_666 yes
C12 H12C O2 0.96 2.58 3.311(4) 133.3 . yes

_refine_diff_density_max         0.458
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.047



####################################################################### 
# 
# 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 2277664'
loop_
_audit_author_name
_audit_author_address
'A. KALILUR RAHIMAN'
;The New College
India
;
_audit_update_record             
;
2023-06-28 deposited with the CCDC.	2024-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        1,5-bis(5-bromosalicylaldehyde)carbohydrazone
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 Br2 N4 O3'
_chemical_formula_sum            'C15 H12 Br2 N4 O3'
_chemical_formula_weight         456.11

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'
Br Br -0.2901 2.4595 '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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

_cell_length_a                   3.85230(10)
_cell_length_b                   12.8505(4)
_cell_length_c                   36.4286(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1803.36(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2351
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      30.47

_exptl_crystal_description       Solid
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    4.515
_shelx_estimated_absorpt_T_min   0.253
_shelx_estimated_absorpt_T_max   0.551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.313
_exptl_absorpt_correction_T_max  0.508
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27732
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         2.236
_diffrn_reflns_theta_max         28.763
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2351
_reflns_number_gt                2004
_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 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008)'
_computing_publication_material  
'WinGX (Farrugia, 2012), pubCIF (Westrip, 2010) and PLATON (Spek, 2009)'
_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)+(0.0147P)²+6.8832P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2351
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1246
_refine_ls_wR_factor_gt          0.1206
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_restrained_S_all      1.198
_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
Br1 Br 0.23165(14) 0.34112(5) 0.47155(2) 0.05596(19) Uani 1 1 d . . . . .
O1 O 1.000000 0.5703(4) 0.250000 0.0588(14) Uani 1 2 d S T P . .
N1 N 0.8088(10) 0.4666(3) 0.31090(9) 0.0429(9) Uani 1 1 d . . . . .
N2 N 0.9051(14) 0.4171(3) 0.27939(10) 0.0501(11) Uani 1 1 d . . . . .
O2 O 0.6991(14) 0.6313(3) 0.35196(11) 0.0689(12) Uani 1 1 d . . . . .
C1 C 0.3772(14) 0.5368(4) 0.43893(12) 0.0511(12) Uani 1 1 d . . . . .
H1 H 0.301362 0.564250 0.461147 0.061 Uiso 1 1 calc R U . . .
C2 C 0.4848(17) 0.6019(4) 0.41114(14) 0.0580(14) Uani 1 1 d . . . . .
H2 H 0.481761 0.673496 0.414792 0.070 Uiso 1 1 calc R U . . .
C3 C 0.5969(14) 0.5626(4) 0.37804(12) 0.0479(11) Uani 1 1 d . . . . .
C4 C 0.6034(12) 0.4548(3) 0.37219(10) 0.0377(9) Uani 1 1 d . . . . .
C5 C 0.7141(14) 0.4096(4) 0.33781(11) 0.0460(11) Uani 1 1 d . . . . .
H5 H 0.716328 0.337583 0.335224 0.055 Uiso 1 1 calc R U . . .
C6 C 1.000000 0.4750(5) 0.250000 0.0431(14) Uani 1 2 d S T P . .
C7 C 0.4958(13) 0.3898(3) 0.40074(11) 0.0398(9) Uani 1 1 d . . . . .
H7 H 0.500496 0.317986 0.397524 0.048 Uiso 1 1 calc R U . . .
C8 C 0.3827(12) 0.4306(4) 0.43357(11) 0.0386(9) Uani 1 1 d . . . . .
H2B H 0.73(2) 0.599(6) 0.332(2) 0.10(3) Uiso 1 1 d . . . . .
H2A H 0.916(13) 0.363(4) 0.2783(12) 0.032(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
Br1 C8 1.891(4) . ?
O1 C6 1.226(7) . ?
N1 C5 1.277(6) . ?
N1 N2 1.364(5) . ?
N2 C6 1.354(5) . ?
N2 H2A 0.70(4) . ?
O2 C3 1.355(6) . ?
O2 H2B 0.85(7) . ?
C1 C2 1.377(7) . ?
C1 C8 1.379(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.402(6) . ?
C4 C7 1.397(6) . ?
C4 C5 1.445(5) . ?
C5 H5 0.9300 . ?
C7 C8 1.377(6) . ?
C7 H7 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
C5 N1 N2 117.1(4) . . ?
C6 N2 N1 118.9(4) . . ?
C6 N2 H2A 119(4) . . ?
N1 N2 H2A 122(4) . . ?
C3 O2 H2B 109(5) . . ?
C2 C1 C8 119.5(4) . . ?
C2 C1 H1 120.2 . . ?
C8 C1 H1 120.2 . . ?
C3 C2 C1 121.0(5) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
O2 C3 C2 117.8(4) . . ?
O2 C3 C4 122.1(4) . . ?
C2 C3 C4 120.1(4) . . ?
C7 C4 C3 118.2(4) . . ?
C7 C4 C5 119.5(4) . . ?
C3 C4 C5 122.3(4) . . ?
N1 C5 C4 121.3(4) . . ?
N1 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
O1 C6 N2 123.3(3) . 3_755 ?
O1 C6 N2 123.3(3) . . ?
N2 C6 N2 113.4(6) 3_755 . ?
C8 C7 C4 120.9(4) . . ?
C8 C7 H7 119.6 . . ?
C4 C7 H7 119.6 . . ?
C7 C8 C1 120.3(4) . . ?
C7 C8 Br1 120.1(3) . . ?
C1 C8 Br1 119.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 C6 178.6(4) . . . . ?
C8 C1 C2 C3 0.2(9) . . . . ?
C1 C2 C3 O2 -180.0(6) . . . . ?
C1 C2 C3 C4 -0.1(9) . . . . ?
O2 C3 C4 C7 179.5(5) . . . . ?
C2 C3 C4 C7 -0.3(8) . . . . ?
O2 C3 C4 C5 -1.0(8) . . . . ?
C2 C3 C4 C5 179.1(5) . . . . ?
N2 N1 C5 C4 -179.2(5) . . . . ?
C7 C4 C5 N1 178.8(5) . . . . ?
C3 C4 C5 N1 -0.6(8) . . . . ?
N1 N2 C6 O1 -1.0(6) . . . . ?
N1 N2 C6 N2 179.0(6) . . . 3_755 ?
C3 C4 C7 C8 0.7(7) . . . . ?
C5 C4 C7 C8 -178.8(5) . . . . ?
C4 C7 C8 C1 -0.6(7) . . . . ?
C4 C7 C8 Br1 179.0(4) . . . . ?
C2 C1 C8 C7 0.2(8) . . . . ?
C2 C1 C8 Br1 -179.5(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2B N1 0.85(7) 1.89(7) 2.625(5) 145(7) . yes

_refine_diff_density_max         0.786
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.087



_exptl_crystal_recrystallization_method 'Slow evaporation'
