# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_K5N
_database_code_depnum_ccdc_archive 'CCDC 2151232'
loop_
_audit_author_name
_audit_author_address
'E. Manoj'
;CUSAT
India
;
_audit_update_record             
;
2022-02-10 deposited with the CCDC.	2024-04-19 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         'C15 H11 I4 N5 O2, C2 H6 O S'

_chemical_formula_sum            'C17 H17 I4 N5 O3 S'
_chemical_formula_weight         879.01

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'
I I -0.4742 1.8119 '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           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

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

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

_cell_length_a                   9.4024(3)
_cell_length_b                   6.9264(2)
_cell_length_c                   19.9477(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.0970(10)
_cell_angle_gamma                90
_cell_volume                     1278.97(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)

_cell_measurement_reflns_used    9341
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      33.02
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.283
_exptl_crystal_F_000             812
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.981
_shelx_estimated_absorpt_T_min   0.436
_shelx_estimated_absorpt_T_max   0.636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4969
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(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            60045
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.119
_diffrn_reflns_theta_max         33.160
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5213
_reflns_number_gt                4031
_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, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'



_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)+(0.0227P)²+2.8161P] 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         5213
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1699(5) 0.250000 0.2387(2) 0.0381(9) Uani 1 2 d S T P . .
H1 H 0.078814 0.250000 0.250801 0.046 Uiso 1 2 calc R U P . .
C2 C 0.1832(5) 0.250000 0.1702(2) 0.0368(9) Uani 1 2 d S T P . .
C3 C 0.3187(5) 0.250000 0.1516(2) 0.0384(9) Uani 1 2 d S T P . .
H3 H 0.327343 0.250000 0.105855 0.046 Uiso 1 2 calc R U P . .
C4 C 0.4395(5) 0.250000 0.2012(2) 0.0373(9) Uani 1 2 d S T P . .
C5 C 0.4308(5) 0.250000 0.2702(2) 0.0355(8) Uani 1 2 d S T P . .
C6 C 0.2937(5) 0.250000 0.2893(2) 0.0345(8) Uani 1 2 d S T P . .
C7 C 0.2769(5) 0.250000 0.3604(2) 0.0415(10) Uani 1 2 d S T P . .
H7 H 0.184800 0.250000 0.371436 0.050 Uiso 1 2 calc R U P . .
C8 C 0.4839(5) 0.250000 0.5253(2) 0.0456(11) Uani 1 2 d S T P . .
C9 C 0.5393(5) 0.250000 0.6977(2) 0.0435(10) Uani 1 2 d S T P . .
H9 H 0.442356 0.250000 0.702003 0.052 Uiso 1 2 calc R U P . .
C10 C 0.6482(5) 0.250000 0.7587(2) 0.0351(8) Uani 1 2 d S T P . .
C11 C 0.6040(5) 0.250000 0.8220(2) 0.0393(9) Uani 1 2 d S T P . .
H11 H 0.505975 0.250000 0.824018 0.047 Uiso 1 2 calc R U P . .
C12 C 0.7034(5) 0.250000 0.8811(2) 0.0396(9) Uani 1 2 d S T P . .
C13 C 0.8508(5) 0.250000 0.8793(2) 0.0393(9) Uani 1 2 d S T P . .
H13 H 0.918085 0.250000 0.919511 0.047 Uiso 1 2 calc R U P . .
C14 C 0.8957(5) 0.250000 0.8165(2) 0.0384(9) Uani 1 2 d S T P . .
C15 C 0.7950(5) 0.250000 0.7562(2) 0.0374(9) Uani 1 2 d S T P . .
C16 C 0.1156(5) 0.4432(8) 0.6137(2) 0.0714(13) Uani 1 1 d . . . . .
H16A H 0.082660 0.449195 0.656591 0.107 Uiso 1 1 calc R U . . .
H16B H 0.218122 0.422737 0.621522 0.107 Uiso 1 1 calc R U . . .
H16C H 0.093252 0.562387 0.589589 0.107 Uiso 1 1 calc R U . . .
N1 N 0.3887(4) 0.250000 0.40835(18) 0.0441(9) Uani 1 2 d S T P . .
N3 N 0.4514(5) 0.250000 0.58574(19) 0.0504(11) Uani 1 2 d S T P . .
N4 N 0.5719(4) 0.250000 0.63766(18) 0.0431(9) Uani 1 2 d S T P . .
O1 O 0.5539(4) 0.250000 0.31619(18) 0.0572(10) Uani 1 2 d S T P . .
H1A H 0.534646 0.250000 0.354715 0.086 Uiso 1 2 calc R U P . .
O2 O 0.8435(4) 0.250000 0.69581(17) 0.0537(9) Uani 1 2 d S T P . .
H2 H 0.774461 0.250000 0.664359 0.081 Uiso 1 2 calc R U P . .
O3 O 0.0849(5) 0.250000 0.49879(19) 0.0734(14) Uani 1 2 d S T P . .
I1 I -0.00062(4) 0.250000 0.09381(2) 0.05035(10) Uani 1 2 d S T P . .
I2 I 0.64300(4) 0.250000 0.17323(2) 0.06998(14) Uani 1 2 d S T P . .
I3 I 1.11540(4) 0.250000 0.81319(2) 0.06681(13) Uani 1 2 d S T P . .
I4 I 0.63526(4) 0.250000 0.97522(2) 0.07334(15) Uani 1 2 d S T P . .
S1 S 0.02817(15) 0.250000 0.56471(7) 0.0647(4) Uani 1 2 d S T P . .
N2 N 0.3679(5) 0.250000 0.4737(2) 0.0562(13) Uani 1 2 d S T P . .
N5 N 0.6157(5) 0.250000 0.5096(2) 0.081(2) Uani 1 2 d S T P . .
H5A H 0.690432 0.250000 0.541386 0.097 Uiso 1 2 calc R U P . .
H5B H 0.626220 0.250000 0.467609 0.097 Uiso 1 2 calc R U P . .
H2A H 0.284(7) 0.250000 0.484(3) 0.058(18) Uiso 1 2 d S . P . .


_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 1.394(6) . ?
C1 C6 1.400(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.388(6) . ?
C2 I1 2.094(4) . ?
C3 C4 1.370(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(6) . ?
C4 I2 2.085(4) . ?
C5 O1 1.345(5) . ?
C5 C6 1.407(6) . ?
C6 C7 1.455(6) . ?
C7 N1 1.291(6) . ?
C7 H7 0.9300 . ?
C8 N3 1.294(6) . ?
C8 N5 1.331(7) . ?
C8 N2 1.362(6) . ?
C9 N4 1.287(6) . ?
C9 C10 1.446(6) . ?
C9 H9 0.9300 . ?
C10 C15 1.389(6) . ?
C10 C11 1.397(6) . ?
C11 C12 1.370(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.393(7) . ?
C12 I4 2.087(4) . ?
C13 C14 1.391(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.396(6) . ?
C14 I3 2.078(5) . ?
C15 O2 1.360(5) . ?
C16 S1 1.772(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 N2 1.352(5) . ?
N3 N4 1.394(5) . ?
O1 H1A 0.8200 . ?
O2 H2 0.8200 . ?
O3 S1 1.503(4) . ?
N2 H2A 0.85(7) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?

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 C6 120.0(4) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 I1 119.0(3) . . ?
C1 C2 I1 120.6(3) . . ?
C4 C3 C2 119.4(4) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 122.0(4) . . ?
C3 C4 I2 119.4(3) . . ?
C5 C4 I2 118.7(3) . . ?
O1 C5 C4 118.7(4) . . ?
O1 C5 C6 122.5(4) . . ?
C4 C5 C6 118.8(4) . . ?
C1 C6 C5 119.4(4) . . ?
C1 C6 C7 119.0(4) . . ?
C5 C6 C7 121.6(4) . . ?
N1 C7 C6 120.6(4) . . ?
N1 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
N3 C8 N5 126.9(5) . . ?
N3 C8 N2 114.6(5) . . ?
N5 C8 N2 118.5(4) . . ?
N4 C9 C10 122.2(4) . . ?
N4 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C15 C10 C11 119.1(4) . . ?
C15 C10 C9 122.1(4) . . ?
C11 C10 C9 118.8(4) . . ?
C12 C11 C10 120.8(4) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.6(4) . . ?
C11 C12 I4 120.3(4) . . ?
C13 C12 I4 119.1(3) . . ?
C14 C13 C12 118.9(4) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 120.7(4) . . ?
C13 C14 I3 119.3(3) . . ?
C15 C14 I3 120.0(3) . . ?
O2 C15 C10 121.4(4) . . ?
O2 C15 C14 118.8(4) . . ?
C10 C15 C14 119.8(4) . . ?
S1 C16 H16A 109.5 . . ?
S1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
S1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 N1 N2 118.5(4) . . ?
C8 N3 N4 113.5(4) . . ?
C9 N4 N3 113.3(4) . . ?
C5 O1 H1A 109.5 . . ?
C15 O2 H2 109.5 . . ?
O3 S1 C16 106.33(19) . 4_565 ?
O3 S1 C16 106.33(19) . . ?
C16 S1 C16 98.1(3) 4_565 . ?
N1 N2 C8 119.8(4) . . ?
N1 N2 H2A 123(4) . . ?
C8 N2 H2A 118(4) . . ?
C8 N5 H5A 120.0 . . ?
C8 N5 H5B 120.0 . . ?
H5A N5 H5B 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
C6 C1 C2 C3 0.000(1) . . . . ?
C6 C1 C2 I1 180.000(1) . . . . ?
C1 C2 C3 C4 0.000(1) . . . . ?
I1 C2 C3 C4 180.000(0) . . . . ?
C2 C3 C4 C5 0.000(1) . . . . ?
C2 C3 C4 I2 180.000(0) . . . . ?
C3 C4 C5 O1 180.000(1) . . . . ?
I2 C4 C5 O1 0.000(1) . . . . ?
C3 C4 C5 C6 0.000(1) . . . . ?
I2 C4 C5 C6 180.000(1) . . . . ?
C2 C1 C6 C5 0.000(1) . . . . ?
C2 C1 C6 C7 180.000(1) . . . . ?
O1 C5 C6 C1 180.000(1) . . . . ?
C4 C5 C6 C1 0.000(1) . . . . ?
O1 C5 C6 C7 0.000(1) . . . . ?
C4 C5 C6 C7 180.000(1) . . . . ?
C1 C6 C7 N1 180.000(1) . . . . ?
C5 C6 C7 N1 0.000(1) . . . . ?
N4 C9 C10 C15 0.000(3) . . . . ?
N4 C9 C10 C11 180.000(2) . . . . ?
C15 C10 C11 C12 0.000(3) . . . . ?
C9 C10 C11 C12 180.000(3) . . . . ?
C10 C11 C12 C13 0.000(3) . . . . ?
C10 C11 C12 I4 180.000(2) . . . . ?
C11 C12 C13 C14 0.000(3) . . . . ?
I4 C12 C13 C14 180.000(2) . . . . ?
C12 C13 C14 C15 0.000(3) . . . . ?
C12 C13 C14 I3 180.000(2) . . . . ?
C11 C10 C15 O2 180.000(2) . . . . ?
C9 C10 C15 O2 0.000(3) . . . . ?
C11 C10 C15 C14 0.000(3) . . . . ?
C9 C10 C15 C14 180.000(2) . . . . ?
C13 C14 C15 O2 180.000(2) . . . . ?
I3 C14 C15 O2 0.000(2) . . . . ?
C13 C14 C15 C10 0.000(3) . . . . ?
I3 C14 C15 C10 180.000(2) . . . . ?
C6 C7 N1 N2 180.000(1) . . . . ?
N5 C8 N3 N4 0.000(2) . . . . ?
N2 C8 N3 N4 180.000(2) . . . . ?
C10 C9 N4 N3 180.000(2) . . . . ?
C8 N3 N4 C9 180.000(2) . . . . ?
C7 N1 N2 C8 180.000(1) . . . . ?
N3 C8 N2 N1 180.000(2) . . . . ?
N5 C8 N2 N1 0.000(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C16 H16C O3 0.96 2.56 3.409(6) 147.1 3_566 yes
O1 H1A N1 0.82 1.88 2.607(5) 146.7 . yes
O2 H2 N4 0.82 1.89 2.614(5) 147.3 . yes
N2 H2A O3 0.85(7) 1.94(7) 2.793(6) 174(6) . yes

_refine_diff_density_max         1.742
_refine_diff_density_min         -1.608
_refine_diff_density_rms         0.105

