# Supplementary Information (SI) 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_A4_perchlorate
_database_code_depnum_ccdc_archive 'CCDC 2357348'
loop_
_audit_author_name
_audit_author_address
'Volodymyr Semeniuchenko'
;University of Ottawa
Canada
;
_audit_update_record             
;
2024-05-22 deposited with the CCDC.	2024-09-06 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V131 by Daniel Kratzert, Freiburg 2023, 
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'6-(butylamino)-12-oxo-12H-quinoxalino[2,1-b]quinazolin-5-ium perchlorate'
_chemical_name_common            
'6-(butylamino)-12-oxo-12H-quinoxalino[2,1-b]quinazolin-5-ium perchlorate'
_chemical_formula_sum            'C19 H19 Cl N4 O5'
_chemical_formula_moiety         'C19 H19 N4 O, Cl O4'
_chemical_formula_weight         418.83
_chemical_melting_point          ?
_symmetry_cell_setting           monoclinic
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_symmetry_space_group_name_H-M   P2(1)/n
_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                   8.416(3)
_cell_length_b                   14.747(5)
_cell_length_c                   15.257(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.503(8)
_cell_angle_gamma                90
_cell_volume                     1841.3(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2678
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      24.43
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method 
'Slow evaporation from ethanol - aqueous perchloric acid solution'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.139
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_T_max  0.9583
_exptl_absorpt_process_details   
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.966
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Triumph Monochromator, parallel (Graphite)'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'sealed X-ray tube tube'
_diffrn_source_type              'Siemens KFF Mo 2K-90 Ceramic'
_diffrn_source_voltage           50
_diffrn_source_current           30
_diffrn_detector                 CCD
_diffrn_detector_type            'Bruker APEXII'
_diffrn_detector_area_resol_mean 8.3
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            25247
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_theta_min         1.947
_diffrn_reflns_theta_max         28.299
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4580
_reflns_number_gt                2986
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  SHELXL-2018/3
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0361P)²+0.9336P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         4580
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'
Cl Cl 0.1484 0.1585 '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'

_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_
_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 0.66498(7) 0.31141(4) 0.09570(4) 0.02342(13) Uani 1 1 d . . . . .
O1 O 0.49365(17) 0.64345(10) 0.49414(10) 0.0224(3) Uani 1 1 d . . . . .
O2 O 0.6012(2) 0.38824(11) 0.04189(12) 0.0387(4) Uani 1 1 d . . . . .
O3 O 0.65163(19) 0.23168(10) 0.03812(10) 0.0277(4) Uani 1 1 d . . . . .
O4 O 0.5695(2) 0.29417(11) 0.16203(10) 0.0300(4) Uani 1 1 d . . . . .
O5 O 0.8330(2) 0.32564(12) 0.14006(11) 0.0382(4) Uani 1 1 d . . . . .
N1 N 0.65557(19) 0.53376(11) 0.44987(11) 0.0159(4) Uani 1 1 d . . . . .
N2 N 0.5769(2) 0.47555(12) 0.29935(12) 0.0206(4) Uani 1 1 d . . . . .
N3 N 0.8660(2) 0.38440(12) 0.48663(12) 0.0194(4) Uani 1 1 d . . . . .
N4 N 0.7559(2) 0.32902(12) 0.34212(12) 0.0212(4) Uani 1 1 d . . . . .
C1 C 0.6602(3) 0.47161(14) 0.38210(14) 0.0196(4) Uani 1 1 d . . . . .
C2 C 0.5285(2) 0.60077(14) 0.43284(15) 0.0201(5) Uani 1 1 d . . . . .
C3 C 0.4450(3) 0.61083(14) 0.33753(14) 0.0197(4) Uani 1 1 d . . . . .
C4 C 0.3314(3) 0.68147(15) 0.31158(15) 0.0249(5) Uani 1 1 d . . . . .
H4 H 0.310391 0.723019 0.355096 0.030 Uiso 1 1 calc R U . . .
C5 C 0.2510(3) 0.68966(16) 0.22209(16) 0.0277(5) Uani 1 1 d . . . . .
H5 H 0.173995 0.737086 0.203814 0.033 Uiso 1 1 calc R U . . .
C6 C 0.2825(3) 0.62822(16) 0.15808(16) 0.0289(5) Uani 1 1 d . . . . .
H6 H 0.228525 0.635498 0.096448 0.035 Uiso 1 1 calc R U . . .
C7 C 0.3900(3) 0.55779(16) 0.18299(15) 0.0253(5) Uani 1 1 d . . . . .
H7 H 0.408651 0.515763 0.139264 0.030 Uiso 1 1 calc R U . . .
C8 C 0.4725(3) 0.54849(15) 0.27416(15) 0.0228(5) Uani 1 1 d . . . . .
C9 C 0.7658(2) 0.39035(14) 0.40472(14) 0.0180(4) Uani 1 1 d . . . . .
C10 C 0.8708(2) 0.45029(14) 0.55293(14) 0.0169(4) Uani 1 1 d . . . . .
C11 C 0.9820(3) 0.43924(14) 0.63611(14) 0.0203(5) Uani 1 1 d . . . . .
H11 H 1.050855 0.387413 0.646525 0.024 Uiso 1 1 calc R U . . .
C12 C 0.9919(3) 0.50335(14) 0.70306(14) 0.0211(5) Uani 1 1 d . . . . .
H12 H 1.065795 0.495192 0.759954 0.025 Uiso 1 1 calc R U . . .
C13 C 0.8933(3) 0.57985(14) 0.68670(15) 0.0225(5) Uani 1 1 d . . . . .
H13 H 0.901612 0.624664 0.732289 0.027 Uiso 1 1 calc R U . . .
C14 C 0.7827(3) 0.59153(14) 0.60456(14) 0.0210(5) Uani 1 1 d . . . . .
H14 H 0.716596 0.644436 0.594161 0.025 Uiso 1 1 calc R U . . .
C15 C 0.7678(2) 0.52600(14) 0.53689(14) 0.0180(4) Uani 1 1 d . . . . .
C16 C 0.8494(3) 0.24386(14) 0.34864(15) 0.0220(5) Uani 1 1 d . . . . .
H16A H 0.950402 0.249615 0.396934 0.026 Uiso 1 1 calc R U . . .
H16B H 0.881673 0.233097 0.291133 0.026 Uiso 1 1 calc R U . . .
C17 C 0.7510(3) 0.16323(15) 0.36888(16) 0.0257(5) Uani 1 1 d . . . . .
H17A H 0.815751 0.107341 0.368064 0.031 Uiso 1 1 calc R U . . .
H17B H 0.650338 0.157965 0.320258 0.031 Uiso 1 1 calc R U . . .
C18 C 0.7029(3) 0.16900(15) 0.45923(16) 0.0288(5) Uani 1 1 d . . . . .
H18A H 0.800442 0.184987 0.506958 0.035 Uiso 1 1 calc R U . . .
H18B H 0.621207 0.217853 0.456385 0.035 Uiso 1 1 calc R U . . .
C19 C 0.6324(3) 0.08064(17) 0.48375(19) 0.0361(6) Uani 1 1 d . . . . .
H19A H 0.536429 0.064249 0.436402 0.054 Uiso 1 1 calc R U . . .
H19B H 0.600359 0.087800 0.541118 0.054 Uiso 1 1 calc R U . . .
H19C H 0.714852 0.032687 0.489585 0.054 Uiso 1 1 calc R U . . .
H1 H 0.677(3) 0.3439(16) 0.2884(17) 0.031(7) Uiso 1 1 d . . . . .
H2 H 0.940(3) 0.3376(18) 0.4979(18) 0.041(8) Uiso 1 1 d . . . . .


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 O2 1.4283(17) . ?
Cl1 O5 1.4333(17) . ?
Cl1 O4 1.4540(16) . ?
Cl1 O3 1.4562(16) . ?
O1 C2 1.218(2) . ?
N1 C1 1.389(3) . ?
N1 C2 1.435(3) . ?
N1 C15 1.443(3) . ?
N2 C1 1.294(3) . ?
N2 C8 1.385(3) . ?
N3 C9 1.337(3) . ?
N3 C10 1.397(3) . ?
N3 H2 0.92(3) . ?
N4 C9 1.304(3) . ?
N4 C16 1.473(3) . ?
N4 H1 0.95(2) . ?
C1 C9 1.484(3) . ?
C2 C3 1.468(3) . ?
C3 C8 1.392(3) . ?
C3 C4 1.406(3) . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.372(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.409(3) . ?
C7 H7 0.9500 . ?
C10 C11 1.399(3) . ?
C10 C15 1.399(3) . ?
C11 C12 1.380(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.398(3) . ?
C14 H14 0.9500 . ?
C16 C17 1.522(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.527(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.515(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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 Cl1 O5 110.61(11) . . ?
O2 Cl1 O4 110.14(11) . . ?
O5 Cl1 O4 109.97(10) . . ?
O2 Cl1 O3 109.15(10) . . ?
O5 Cl1 O3 109.37(10) . . ?
O4 Cl1 O3 107.54(9) . . ?
C1 N1 C2 117.96(17) . . ?
C1 N1 C15 120.43(17) . . ?
C2 N1 C15 121.43(17) . . ?
C1 N2 C8 118.00(19) . . ?
C9 N3 C10 122.43(19) . . ?
C9 N3 H2 118.5(17) . . ?
C10 N3 H2 118.9(17) . . ?
C9 N4 C16 126.87(19) . . ?
C9 N4 H1 112.5(15) . . ?
C16 N4 H1 120.6(15) . . ?
N2 C1 N1 126.42(19) . . ?
N2 C1 C9 114.94(19) . . ?
N1 C1 C9 118.62(18) . . ?
O1 C2 N1 121.31(19) . . ?
O1 C2 C3 124.26(19) . . ?
N1 C2 C3 114.42(18) . . ?
C8 C3 C4 120.4(2) . . ?
C8 C3 C2 120.16(19) . . ?
C4 C3 C2 119.4(2) . . ?
C5 C4 C3 119.2(2) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 119.2(2) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
N2 C8 C3 121.2(2) . . ?
N2 C8 C7 118.9(2) . . ?
C3 C8 C7 119.8(2) . . ?
N4 C9 N3 123.89(19) . . ?
N4 C9 C1 117.20(19) . . ?
N3 C9 C1 118.90(18) . . ?
N3 C10 C11 118.42(19) . . ?
N3 C10 C15 121.11(19) . . ?
C11 C10 C15 120.48(19) . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 119.6(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 118.50(19) . . ?
C14 C15 N1 123.44(19) . . ?
C10 C15 N1 118.02(18) . . ?
N4 C16 C17 111.85(18) . . ?
N4 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
N4 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 C18 114.28(18) . . ?
C16 C17 H17A 108.7 . . ?
C18 C17 H17A 108.7 . . ?
C16 C17 H17B 108.7 . . ?
C18 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 112.1(2) . . ?
C19 C18 H18A 109.2 . . ?
C17 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
C17 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
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 . . ?

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
N4 H1 O4 0.95(2) 2.06(2) 2.874(3) 142(2) . yes
N4 H1 N2 0.95(2) 2.14(2) 2.628(3) 110.5(18) . yes
N3 H2 O3 0.92(3) 2.02(3) 2.906(3) 161(2) 4_666 yes

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 1.00 0.00 0.0870
-1.00 -1.00 0.00 0.0400
-1.00 0.00 0.00 0.0310
1.00 0.00 0.00 0.0880
0.00 1.00 0.00 0.0600
-1.00 1.00 0.00 0.0360
-1.00 1.00 1.00 0.0500
1.00 -1.00 -1.00 0.0690
-1.00 0.00 1.00 0.0420
0.00 0.00 -1.00 0.0710
0.00 0.00 1.00 0.0690
-1.00 -1.00 1.00 0.0350
1.00 1.00 -1.00 0.0900
0.00 1.00 -1.00 0.0580
1.00 0.00 1.00 0.0760
-1.00 1.00 -1.00 0.0520
1.00 -1.00 1.00 0.0680

