#------------------------------------------------------------------------------
#$Date: 2024-04-26 04:05:39 +0300 (Fri, 26 Apr 2024) $
#$Revision: 291363 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/85/7248544.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7248544
loop_
_publ_author_name
'Mohammed Hashim, K. K.'
'Manoj, E.'
_publ_section_title
;
 Aminoguanidine-based bioactive proligand as AIEE probe for anticancer and
 anticovid studies
;
_journal_issue                   19
_journal_name_full               'RSC Advances'
_journal_page_first              13654
_journal_page_last               13668
_journal_paper_doi               10.1039/D4RA00554F
_journal_volume                  14
_journal_year                    2024
_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
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-02-10 deposited with the CCDC.	2024-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.0970(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4024(3)
_cell_length_b                   6.9264(2)
_cell_length_c                   19.9477(6)
_cell_measurement_reflns_used    9341
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      33.02
_cell_measurement_theta_min      2.94
_cell_volume                     1278.97(7)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            60045
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.160
_diffrn_reflns_theta_min         3.119
_exptl_absorpt_coefficient_mu    4.981
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.4969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.283
_exptl_crystal_description       plate
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.742
_refine_diff_density_min         -1.608
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         5213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0394
_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)+(0.0227P)²+2.8161P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0888
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4031
_reflns_number_total             5213
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra00554f2.cif
_cod_data_source_block           K5N
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               7248544
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.436
_shelx_estimated_absorpt_t_max   0.636
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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 . .
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'
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_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_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
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) . . . . ?
