# 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_napsuly_0m
_database_code_depnum_ccdc_archive 'CCDC 2263537'
loop_
_audit_author_name
_audit_author_address
'Muhammad Ashfaq'
;University of Sargodha
Pakistan
;
_audit_update_record             
;
2023-05-17 deposited with the CCDC.	2024-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
1-((Z)-((4-((E)-N-(thiazol-2(3H)-ylidene)sulfamoyl)phenyl)iminio)methylnaphthalen-2-olate
_chemical_formula_moiety         'C20 H15 N3 O3 S2'
_chemical_formula_sum            'C20 H15 N3 O3 S2'
_chemical_formula_iupac          'C20 H15 N3 O3 S2'
_chemical_formula_weight         409.47

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.8389(8)
_cell_length_b                   13.8151(16)
_cell_length_c                   17.198(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.032(4)
_cell_angle_gamma                90
_cell_volume                     1857.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2548
_cell_measurement_theta_min      2.374
_cell_measurement_theta_max      27.000
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_T_max  0.894
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.828
_diffrn_reflns_number            15333
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.374
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total             4040
_reflns_number_gt                2548
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1087
_refine_ls_wR_factor_gt          0.0916
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_number_reflns         4040
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0429P)²+0.3132P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXT2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/2  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2009)
;


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 0.62806(8) 0.37379(5) 0.35983(3) 0.04756(19) Uani 1 1 d . . . . .
S2 S 0.27019(9) 0.27664(5) 0.41242(4) 0.0608(2) Uani 1 1 d . . . . .
O1 O 0.1217(2) 0.41542(13) -0.06501(11) 0.0680(5) Uani 1 1 d . . . . .
O2 O 0.7889(2) 0.42300(13) 0.36955(9) 0.0608(5) Uani 1 1 d . . . . .
O3 O 0.6259(2) 0.27012(12) 0.36427(9) 0.0600(5) Uani 1 1 d . . . . .
N1 N 0.3001(2) 0.48144(15) 0.05142(11) 0.0486(5) Uani 1 1 d . . . . .
H1 H 0.238(3) 0.4297(17) 0.0229(14) 0.058 Uiso 1 1 d . U . . .
N2 N 0.5153(2) 0.42218(13) 0.42388(10) 0.0448(5) Uani 1 1 d . . . . .
N3 N 0.2837(3) 0.42242(15) 0.49937(12) 0.0508(5) Uani 1 1 d . . . . .
H3A H 0.322(3) 0.4750(18) 0.5249(14) 0.061 Uiso 1 1 d . U . . .
C1 C 0.1231(3) 0.49923(19) -0.09520(14) 0.0509(6) Uani 1 1 d . . . . .
C2 C 0.0363(3) 0.5141(2) -0.17026(14) 0.0572(7) Uani 1 1 d . . . . .
H2 H -0.019101 0.462165 -0.195502 0.069 Uiso 1 1 calc R U . . .
C3 C 0.0327(3) 0.6003(2) -0.20484(14) 0.0566(7) Uani 1 1 d . . . . .
H3 H -0.025917 0.606851 -0.253469 0.068 Uiso 1 1 calc R U . . .
C4 C 0.1162(3) 0.68335(18) -0.16976(13) 0.0479(6) Uani 1 1 d . . . . .
C5 C 0.1148(3) 0.7723(2) -0.20827(14) 0.0652(8) Uani 1 1 d . . . . .
H5 H 0.055085 0.778511 -0.256678 0.078 Uiso 1 1 calc R U . . .
C6 C 0.1997(4) 0.8502(2) -0.17602(15) 0.0700(8) Uani 1 1 d . . . . .
H6 H 0.197231 0.909269 -0.201978 0.084 Uiso 1 1 calc R U . . .
C7 C 0.2892(3) 0.8406(2) -0.10451(14) 0.0630(7) Uani 1 1 d . . . . .
H7 H 0.348124 0.893463 -0.082612 0.076 Uiso 1 1 calc R U . . .
C8 C 0.2926(3) 0.75469(18) -0.06548(13) 0.0528(6) Uani 1 1 d . . . . .
H8 H 0.353845 0.750163 -0.017294 0.063 Uiso 1 1 calc R U . . .
C9 C 0.2064(3) 0.67346(17) -0.09614(12) 0.0424(5) Uani 1 1 d . . . . .
C10 C 0.2088(3) 0.57993(17) -0.05741(12) 0.0422(5) Uani 1 1 d . . . . .
C11 C 0.2919(3) 0.56653(18) 0.01579(12) 0.0460(6) Uani 1 1 d . . . . .
H11 H 0.343968 0.619554 0.040893 0.055 Uiso 1 1 calc R U . . .
C12 C 0.3795(3) 0.46035(17) 0.12503(12) 0.0433(5) Uani 1 1 d . . . . .
C13 C 0.4622(3) 0.52816(18) 0.17266(13) 0.0536(6) Uani 1 1 d . . . . .
H13 H 0.467179 0.592349 0.156691 0.064 Uiso 1 1 calc R U . . .
C14 C 0.5374(3) 0.50080(18) 0.24386(13) 0.0542(6) Uani 1 1 d . . . . .
H14 H 0.594324 0.546593 0.275698 0.065 Uiso 1 1 calc R U . . .
C15 C 0.5292(3) 0.40645(17) 0.26843(12) 0.0422(5) Uani 1 1 d . . . . .
C16 C 0.4473(3) 0.33821(17) 0.22109(13) 0.0494(6) Uani 1 1 d . . . . .
H16 H 0.442650 0.274010 0.237083 0.059 Uiso 1 1 calc R U . . .
C17 C 0.3723(3) 0.36588(18) 0.14980(13) 0.0501(6) Uani 1 1 d . . . . .
H17 H 0.315809 0.319999 0.117875 0.060 Uiso 1 1 calc R U . . .
C18 C 0.3718(3) 0.38159(16) 0.44415(12) 0.0431(5) Uani 1 1 d . . . . .
C19 C 0.1106(3) 0.2962(2) 0.47421(17) 0.0673(8) Uani 1 1 d . . . . .
H19 H 0.016556 0.255785 0.477583 0.081 Uiso 1 1 calc R U . . .
C20 C 0.1373(3) 0.3750(2) 0.51617(16) 0.0615(7) Uani 1 1 d . . . . .
H20 H 0.064756 0.396229 0.553157 0.074 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 O2 1.4315(17) . ?
S1 O3 1.4344(17) . ?
S1 N2 1.6056(18) . ?
S1 C15 1.762(2) . ?
S2 C19 1.719(3) . ?
S2 C18 1.724(2) . ?
O1 C1 1.269(3) . ?
N1 C11 1.325(3) . ?
N1 C12 1.402(3) . ?
N1 H1 0.98(2) . ?
N2 C18 1.325(3) . ?
N3 C18 1.338(3) . ?
N3 C20 1.370(3) . ?
N3 H3A 0.89(2) . ?
C1 C2 1.431(3) . ?
C1 C10 1.434(3) . ?
C2 C3 1.331(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.433(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(3) . ?
C4 C9 1.413(3) . ?
C5 C6 1.362(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.379(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.362(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.394(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.453(3) . ?
C10 C11 1.388(3) . ?
C11 H11 0.9300 . ?
C12 C17 1.375(3) . ?
C12 C13 1.376(3) . ?
C13 C14 1.374(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(3) . ?
C16 C17 1.376(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C19 C20 1.315(3) . ?
C19 H19 0.9300 . ?
C20 H20 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
O2 S1 O3 118.78(11) . . ?
O2 S1 N2 104.17(10) . . ?
O3 S1 N2 111.73(10) . . ?
O2 S1 C15 108.12(11) . . ?
O3 S1 C15 107.28(10) . . ?
N2 S1 C15 106.06(10) . . ?
C19 S2 C18 90.71(13) . . ?
C11 N1 C12 127.3(2) . . ?
C11 N1 H1 114.3(14) . . ?
C12 N1 H1 118.3(14) . . ?
C18 N2 S1 121.50(16) . . ?
C18 N3 C20 115.5(2) . . ?
C18 N3 H3A 121.7(16) . . ?
C20 N3 H3A 122.8(16) . . ?
O1 C1 C2 118.8(2) . . ?
O1 C1 C10 122.8(2) . . ?
C2 C1 C10 118.4(2) . . ?
C3 C2 C1 121.7(2) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 122.3(2) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C5 C4 C9 119.8(2) . . ?
C5 C4 C3 121.2(2) . . ?
C9 C4 C3 119.0(2) . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 119.4(2) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 121.0(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 121.5(2) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C4 117.4(2) . . ?
C8 C9 C10 123.51(19) . . ?
C4 C9 C10 119.1(2) . . ?
C11 C10 C1 118.8(2) . . ?
C11 C10 C9 121.6(2) . . ?
C1 C10 C9 119.55(19) . . ?
N1 C11 C10 122.8(2) . . ?
N1 C11 H11 118.6 . . ?
C10 C11 H11 118.6 . . ?
C17 C12 C13 119.3(2) . . ?
C17 C12 N1 116.8(2) . . ?
C13 C12 N1 123.8(2) . . ?
C14 C13 C12 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 119.9(2) . . ?
C14 C15 S1 119.37(17) . . ?
C16 C15 S1 120.70(18) . . ?
C15 C16 C17 119.3(2) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C12 C17 C16 121.0(2) . . ?
C12 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
N2 C18 N3 119.9(2) . . ?
N2 C18 S2 130.88(18) . . ?
N3 C18 S2 109.21(18) . . ?
C20 C19 S2 112.0(2) . . ?
C20 C19 H19 124.0 . . ?
S2 C19 H19 124.0 . . ?
C19 C20 N3 112.5(2) . . ?
C19 C20 H20 123.7 . . ?
N3 C20 H20 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
O2 S1 N2 C18 -165.13(17) . . . . ?
O3 S1 N2 C18 -35.7(2) . . . . ?
C15 S1 N2 C18 80.88(19) . . . . ?
O1 C1 C2 C3 179.8(2) . . . . ?
C10 C1 C2 C3 -0.4(4) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C3 C4 C5 178.1(3) . . . . ?
C2 C3 C4 C9 0.5(4) . . . . ?
C9 C4 C5 C6 0.1(4) . . . . ?
C3 C4 C5 C6 -177.5(3) . . . . ?
C4 C5 C6 C7 0.5(4) . . . . ?
C5 C6 C7 C8 -0.6(4) . . . . ?
C6 C7 C8 C9 0.1(4) . . . . ?
C7 C8 C9 C4 0.5(4) . . . . ?
C7 C8 C9 C10 178.8(2) . . . . ?
C5 C4 C9 C8 -0.6(3) . . . . ?
C3 C4 C9 C8 177.1(2) . . . . ?
C5 C4 C9 C10 -179.0(2) . . . . ?
C3 C4 C9 C10 -1.4(3) . . . . ?
O1 C1 C10 C11 -0.9(3) . . . . ?
C2 C1 C10 C11 179.3(2) . . . . ?
O1 C1 C10 C9 179.3(2) . . . . ?
C2 C1 C10 C9 -0.5(3) . . . . ?
C8 C9 C10 C11 3.3(3) . . . . ?
C4 C9 C10 C11 -178.4(2) . . . . ?
C8 C9 C10 C1 -176.9(2) . . . . ?
C4 C9 C10 C1 1.4(3) . . . . ?
C12 N1 C11 C10 -179.7(2) . . . . ?
C1 C10 C11 N1 2.2(3) . . . . ?
C9 C10 C11 N1 -178.0(2) . . . . ?
C11 N1 C12 C17 -179.6(2) . . . . ?
C11 N1 C12 C13 0.6(4) . . . . ?
C17 C12 C13 C14 0.5(4) . . . . ?
N1 C12 C13 C14 -179.7(2) . . . . ?
C12 C13 C14 C15 -0.7(4) . . . . ?
C13 C14 C15 C16 1.0(4) . . . . ?
C13 C14 C15 S1 179.64(19) . . . . ?
O2 S1 C15 C14 -40.8(2) . . . . ?
O3 S1 C15 C14 -169.98(18) . . . . ?
N2 S1 C15 C14 70.5(2) . . . . ?
O2 S1 C15 C16 137.92(19) . . . . ?
O3 S1 C15 C16 8.7(2) . . . . ?
N2 S1 C15 C16 -110.84(19) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
S1 C15 C16 C17 -179.56(18) . . . . ?
C13 C12 C17 C16 -0.4(3) . . . . ?
N1 C12 C17 C16 179.7(2) . . . . ?
C15 C16 C17 C12 0.6(3) . . . . ?
S1 N2 C18 N3 178.04(16) . . . . ?
S1 N2 C18 S2 -0.2(3) . . . . ?
C20 N3 C18 N2 180.0(2) . . . . ?
C20 N3 C18 S2 -1.4(3) . . . . ?
C19 S2 C18 N2 179.9(2) . . . . ?
C19 S2 C18 N3 1.55(18) . . . . ?
C18 S2 C19 C20 -1.4(2) . . . . ?
S2 C19 C20 N3 0.9(3) . . . . ?
C18 N3 C20 C19 0.3(3) . . . . ?

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
N1 H1 O1 0.98(2) 1.72(2) 2.530(3) 138(2) . yes
N3 H3A S1 0.89(2) 2.89(3) 3.746(2) 163(2) 3_666 yes
N3 H3A O2 0.89(2) 2.50(2) 3.185(3) 134(2) 3_666 yes
N3 H3A N2 0.89(2) 2.07(2) 2.922(3) 161(2) 3_666 yes
C11 H11 O3 0.93 2.64 3.521(3) 157.4 2_655 yes
C13 H13 O3 0.93 2.58 3.463(3) 158.7 2_655 yes

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.043


####################################################################### 
# 
# 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_pymtvan_twnew
_database_code_depnum_ccdc_archive 'CCDC 2263538'
loop_
_audit_author_name
_audit_author_address
'Muhammad Ashfaq'
;University of Sargodha
Pakistan
;
_audit_update_record             
;
2023-05-17 deposited with the CCDC.	2024-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
(E)-1-(((4-amino-5-(4-chlorophenyl)-6-ethylpyrimidin-2-yl)iminio)methyl)
naphthalen-2-olate
;
_chemical_formula_moiety         'C23 H19 Cl N4 O'
_chemical_formula_sum            'C23 H19 Cl N4 O'
_chemical_formula_iupac          'C23 H19 Cl N4 O'
_chemical_formula_weight         402.87

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'
Cl Cl 0.1484 0.1585 '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                   4.5436(6)
_cell_length_b                   12.5255(16)
_cell_length_c                   17.673(2)
_cell_angle_alpha                88.308(8)
_cell_angle_beta                 89.195(8)
_cell_angle_gamma                82.611(9)
_cell_volume                     996.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2397
_cell_measurement_theta_min      1.640
_cell_measurement_theta_max      27.448
_cell_measurement_temperature    296(2)
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_T_max  0.894
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.710
_diffrn_reflns_number            4351
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.640
_diffrn_reflns_theta_max         27.448
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total             4351
_reflns_number_gt                2397
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1311
_refine_ls_R_factor_gt           0.0763
_refine_ls_wR_factor_ref         0.2358
_refine_ls_wR_factor_gt          0.2131
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_refine_ls_number_reflns         4351
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0757P)²+0.7915P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXT2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2019/2  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2009)
;


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
Cl1 Cl 0.8437(5) 0.66072(16) -0.44259(7) 0.1244(8) Uani 1 1 d . . . . .
O1 O 1.5052(8) 0.6311(2) 0.22359(17) 0.0647(9) Uani 1 1 d . . . . .
N1 N 1.1691(8) 0.7121(2) 0.11607(17) 0.0506(9) Uani 1 1 d . . . . .
H1 H 1.316681 0.667310 0.131723 0.061 Uiso 1 1 calc R U . . .
N2 N 1.2336(8) 0.6206(3) 0.00662(17) 0.0515(9) Uani 1 1 d . . . . .
N3 N 1.3058(9) 0.5222(3) -0.09936(18) 0.0620(10) Uani 1 1 d . . . . .
H3A H 1.422638 0.476107 -0.073272 0.074 Uiso 1 1 calc R U . . .
H3B H 1.275403 0.511139 -0.146252 0.074 Uiso 1 1 calc R U . . .
N4 N 0.8944(8) 0.7821(2) 0.01133(18) 0.0490(8) Uani 1 1 d . . . . .
C1 C 1.3595(10) 0.6975(3) 0.2669(2) 0.0519(10) Uani 1 1 d . . . . .
C2 C 1.4275(11) 0.6933(4) 0.3474(2) 0.0606(12) Uani 1 1 d . . . . .
H2 H 1.576803 0.641685 0.365800 0.073 Uiso 1 1 calc R U . . .
C3 C 1.2799(11) 0.7618(4) 0.3950(2) 0.0606(12) Uani 1 1 d . . . . .
H3 H 1.330356 0.756311 0.445923 0.073 Uiso 1 1 calc R U . . .
C4 C 1.0470(10) 0.8437(3) 0.3713(2) 0.0530(11) Uani 1 1 d . . . . .
C5 C 0.8982(12) 0.9153(4) 0.4231(2) 0.0629(13) Uani 1 1 d . . . . .
H5 H 0.948896 0.908272 0.473926 0.075 Uiso 1 1 calc R U . . .
C6 C 0.6814(12) 0.9948(4) 0.4005(3) 0.0683(13) Uani 1 1 d . . . . .
H6 H 0.587866 1.042410 0.435310 0.082 Uiso 1 1 calc R U . . .
C7 C 0.6019(11) 1.0036(4) 0.3247(2) 0.0625(12) Uani 1 1 d . . . . .
H7 H 0.451165 1.056642 0.308993 0.075 Uiso 1 1 calc R U . . .
C8 C 0.7432(10) 0.9353(3) 0.2731(2) 0.0554(11) Uani 1 1 d . . . . .
H8 H 0.687906 0.943491 0.222608 0.067 Uiso 1 1 calc R U . . .
C9 C 0.9688(10) 0.8531(3) 0.2940(2) 0.0455(9) Uani 1 1 d . . . . .
C10 C 1.1248(9) 0.7779(3) 0.2408(2) 0.0441(9) Uani 1 1 d . . . . .
C11 C 1.0389(10) 0.7792(3) 0.1662(2) 0.0479(10) Uani 1 1 d . . . . .
H11 H 0.881995 0.829698 0.150473 0.057 Uiso 1 1 calc R U . . .
C12 C 1.0917(10) 0.7062(3) 0.0402(2) 0.0459(9) Uani 1 1 d . . . . .
C13 C 1.1704(10) 0.6115(3) -0.0668(2) 0.0488(10) Uani 1 1 d . . . . .
C14 C 0.9780(9) 0.6917(3) -0.1065(2) 0.0434(9) Uani 1 1 d . . . . .
C15 C 0.8397(9) 0.7750(3) -0.0636(2) 0.0448(9) Uani 1 1 d . . . . .
C16 C 0.6198(10) 0.8645(3) -0.0940(2) 0.0551(11) Uani 1 1 d . . . . .
H16A H 0.438920 0.867660 -0.063915 0.066 Uiso 1 1 calc R U . . .
H16B H 0.571511 0.848972 -0.145513 0.066 Uiso 1 1 calc R U . . .
C17 C 0.7319(12) 0.9725(3) -0.0936(3) 0.0760(15) Uani 1 1 d . . . . .
H17A H 0.808426 0.983545 -0.044450 0.114 Uiso 1 1 calc R U . . .
H17B H 0.571904 1.028182 -0.105070 0.114 Uiso 1 1 calc R U . . .
H17C H 0.886726 0.974607 -0.130896 0.114 Uiso 1 1 calc R U . . .
C18 C 0.9410(9) 0.6853(3) -0.1905(2) 0.0461(9) Uani 1 1 d . . . . .
C19 C 1.0302(11) 0.7619(3) -0.2399(2) 0.0570(11) Uani 1 1 d . . . . .
H19 H 1.112091 0.819797 -0.220837 0.068 Uiso 1 1 calc R U . . .
C20 C 1.0012(12) 0.7551(4) -0.3177(2) 0.0683(13) Uani 1 1 d . . . . .
H20 H 1.061097 0.807895 -0.350439 0.082 Uiso 1 1 calc R U . . .
C21 C 0.8825(12) 0.6690(4) -0.3453(2) 0.0665(13) Uani 1 1 d . . . . .
C22 C 0.7958(13) 0.5910(4) -0.2986(3) 0.0749(15) Uani 1 1 d . . . . .
H22 H 0.716106 0.532999 -0.318188 0.090 Uiso 1 1 calc R U . . .
C23 C 0.8277(11) 0.5989(4) -0.2210(2) 0.0635(13) Uani 1 1 d . . . . .
H23 H 0.771632 0.544828 -0.188875 0.076 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
Cl1 C21 1.739(4) . ?
O1 C1 1.263(5) . ?
N1 C11 1.320(5) . ?
N1 C12 1.397(5) . ?
N1 H1 0.8600 . ?
N2 C12 1.330(5) . ?
N2 C13 1.344(5) . ?
N3 C13 1.346(5) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 C12 1.316(5) . ?
N4 C15 1.358(5) . ?
C1 C10 1.440(6) . ?
C1 C2 1.458(5) . ?
C2 C3 1.332(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.433(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.404(6) . ?
C4 C9 1.416(5) . ?
C5 C6 1.362(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.389(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.366(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.401(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.461(5) . ?
C10 C11 1.379(5) . ?
C11 H11 0.9300 . ?
C13 C14 1.419(5) . ?
C14 C15 1.387(5) . ?
C14 C18 1.501(5) . ?
C15 C16 1.495(5) . ?
C16 C17 1.506(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.375(5) . ?
C18 C23 1.383(6) . ?
C19 C20 1.389(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.371(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.354(6) . ?
C22 C23 1.388(6) . ?
C22 H22 0.9300 . ?
C23 H23 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
C11 N1 C12 126.7(4) . . ?
C11 N1 H1 116.7 . . ?
C12 N1 H1 116.7 . . ?
C12 N2 C13 115.6(3) . . ?
C13 N3 H3A 120.0 . . ?
C13 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C12 N4 C15 115.8(3) . . ?
O1 C1 C10 123.1(3) . . ?
O1 C1 C2 119.3(4) . . ?
C10 C1 C2 117.6(4) . . ?
C3 C2 C1 121.3(4) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 123.0(4) . . ?
C2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
C5 C4 C9 119.5(4) . . ?
C5 C4 C3 121.4(4) . . ?
C9 C4 C3 119.1(4) . . ?
C6 C5 C4 121.6(4) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 119.1(4) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 120.6(5) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 122.0(4) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C8 C9 C4 117.2(4) . . ?
C8 C9 C10 123.9(3) . . ?
C4 C9 C10 119.0(4) . . ?
C11 C10 C1 119.3(4) . . ?
C11 C10 C9 120.5(4) . . ?
C1 C10 C9 120.1(3) . . ?
N1 C11 C10 123.0(4) . . ?
N1 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
N4 C12 N2 128.5(3) . . ?
N4 C12 N1 118.6(3) . . ?
N2 C12 N1 113.0(3) . . ?
N2 C13 N3 115.0(4) . . ?
N2 C13 C14 121.8(3) . . ?
N3 C13 C14 123.2(3) . . ?
C15 C14 C13 116.1(3) . . ?
C15 C14 C18 123.7(3) . . ?
C13 C14 C18 120.2(3) . . ?
N4 C15 C14 122.1(4) . . ?
N4 C15 C16 113.6(3) . . ?
C14 C15 C16 124.3(3) . . ?
C15 C16 C17 113.0(4) . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C17 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 117.5(4) . . ?
C19 C18 C14 121.6(4) . . ?
C23 C18 C14 120.8(3) . . ?
C18 C19 C20 121.7(4) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C21 C20 C19 118.7(4) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C22 C21 C20 121.5(4) . . ?
C22 C21 Cl1 119.7(4) . . ?
C20 C21 Cl1 118.8(4) . . ?
C21 C22 C23 119.0(4) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C18 C23 C22 121.6(4) . . ?
C18 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?

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
N1 H1 O1 0.86 1.86 2.557(4) 136.6 . yes
N3 H3A N2 0.86 2.19 3.037(5) 170.8 2_865 yes
N3 H3B O1 0.86 2.38 3.003(5) 129.2 2_865 yes

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.079


