# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_FTCAAP
_database_code_depnum_ccdc_archive 'CCDC 2057691'
loop_
_audit_author_name
_audit_author_address
'Yasser Azim'
;Aligarh Muslim University
India
;
_audit_update_record             
;
2021-01-21 deposited with the CCDC.	2021-06-08 downloaded from the CCDC.
;
_audit_creation_date             2020-09-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
'Tetrahydrofuran-2,3,4,5-tetracarboxylic acid + 2-aminopyrimidine'
_chemical_name_systematic        
'Tetrahydrofuran-2,3,4,5-tetracarboxylic acid + 2-aminopyrimidine'
_chemical_formula_moiety         'C8 H7 O9, C4 H6 N3'
_chemical_formula_sum            'C12 H13 N3 O9'
_chemical_formula_weight         343.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.8226(9)
_cell_length_b                   13.7338(8)
_cell_length_c                   9.9166(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.482(9)
_cell_angle_gamma                90
_cell_volume                     1413.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2619
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.6580
_cell_measurement_theta_min      3.6510
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.229
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.093
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4424
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        66.988
_diffrn_reflns_theta_max         66.988
_diffrn_reflns_theta_min         4.260
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1955
_reflns_number_total             2459
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2459
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0550P)²+0.4216P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1230
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C7(H7), C6(H6A), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4A), C2(H2), C3(H3)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O4 O 0.90279(17) 0.59856(12) 0.0763(2) 0.0432(4) Uani 1 1 d . . . . .
H4 H 0.863347 0.548324 0.081259 0.065 Uiso 1 1 calc R U . . .
O1 O 0.70323(18) 0.33631(11) 0.2167(2) 0.0415(4) Uani 1 1 d . . . . .
O3 O 0.65185(15) 0.56003(10) 0.03790(15) 0.0298(3) Uani 1 1 d . . . . .
O2 O 0.83160(17) 0.42389(11) 0.1246(2) 0.0411(4) Uani 1 1 d . . . . .
O6 O 0.53027(17) 0.79470(11) 0.26053(19) 0.0418(4) Uani 1 1 d . . . . .
H6 H 0.456217 0.808006 0.259798 0.063 Uiso 1 1 calc R U . . .
O7 O 0.43909(18) 0.66393(14) 0.1394(2) 0.0534(5) Uani 1 1 d . . . . .
N1 N 0.8168(2) 0.16260(14) 0.1995(2) 0.0396(5) Uani 1 1 d . . . . .
H1 H 0.785894 0.217721 0.215358 0.047 Uiso 1 1 calc R U . . .
N3 N 0.9451(2) 0.07444(14) 0.0873(2) 0.0421(5) Uani 1 1 d . . . . .
N2 N 0.9261(2) 0.24035(14) 0.0622(3) 0.0497(6) Uani 1 1 d . . . . .
H2A H 0.976427 0.238673 0.008910 0.060 Uiso 1 1 calc R U . . .
H2B H 0.895343 0.295011 0.080110 0.060 Uiso 1 1 calc R U . . .
C9 C 0.6677(2) 0.67028(13) 0.2267(2) 0.0265(4) Uani 1 1 d . . . . .
H9 H 0.731621 0.714306 0.286147 0.032 Uiso 1 1 calc R U . . .
O5 O 0.8731(2) 0.75562(12) 0.0900(2) 0.0528(5) Uani 1 1 d . . . . .
O8 O 0.5729(3) 0.60910(14) 0.4529(2) 0.0658(7) Uani 1 1 d . . . . .
O9 O 0.5918(3) 0.45395(13) 0.4097(2) 0.0668(7) Uani 1 1 d . . . . .
C1 C 0.8961(2) 0.15893(16) 0.1166(2) 0.0359(5) Uani 1 1 d . . . . .
C7 C 0.6837(2) 0.56517(13) 0.2857(2) 0.0258(4) Uani 1 1 d . . . . .
H7 H 0.775230 0.553792 0.332307 0.031 Uiso 1 1 calc R U . . .
C10 C 0.5326(2) 0.70828(15) 0.2045(2) 0.0312(5) Uani 1 1 d . . . . .
C8 C 0.6080(2) 0.54062(15) 0.3878(2) 0.0303(5) Uani 1 1 d . . . . .
C12 C 0.8315(2) 0.67348(15) 0.0845(2) 0.0330(5) Uani 1 1 d . . . . .
C4 C 0.7852(3) 0.08103(19) 0.2581(3) 0.0432(6) Uani 1 1 d . . . . .
H4A H 0.731553 0.084562 0.316483 0.052 Uiso 1 1 calc R U . . .
C2 C 0.9125(3) -0.00530(17) 0.1440(3) 0.0424(6) Uani 1 1 d . . . . .
H2 H 0.945338 -0.064481 0.124280 0.051 Uiso 1 1 calc R U . . .
C3 C 0.8321(3) -0.00599(18) 0.2311(3) 0.0450(6) Uani 1 1 d . . . . .
H3 H 0.811475 -0.063541 0.269208 0.054 Uiso 1 1 calc R U . . .
C6 C 0.64275(19) 0.50023(13) 0.1521(2) 0.0253(4) Uani 1 1 d . . . . .
H6A H 0.553789 0.477954 0.136706 0.030 Uiso 1 1 calc R U . . .
C11 C 0.6917(2) 0.65571(14) 0.0820(2) 0.0279(4) Uani 1 1 d . . . . .
H11 H 0.636986 0.701487 0.015350 0.033 Uiso 1 1 calc R U . . .
C5 C 0.7327(2) 0.41276(14) 0.1642(2) 0.0304(5) Uani 1 1 d . . . . .
H8 H 0.513(7) 0.586(4) 0.509(7) 0.16(2) 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
O4 H4 0.8200 . ?
O4 C12 1.302(3) . ?
O1 C5 1.252(3) . ?
O3 C6 1.425(2) . ?
O3 C11 1.413(2) . ?
O2 C5 1.250(3) . ?
O6 H6 0.8200 . ?
O6 C10 1.314(3) . ?
O7 C10 1.201(3) . ?
N1 H1 0.8600 . ?
N1 C1 1.347(3) . ?
N1 C4 1.350(3) . ?
N3 C1 1.342(3) . ?
N3 C2 1.324(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C1 1.321(3) . ?
C9 H9 0.9800 . ?
C9 C7 1.549(2) . ?
C9 C10 1.509(3) . ?
C9 C11 1.542(3) . ?
O5 C12 1.210(3) . ?
O8 C8 1.259(3) . ?
O8 H8 1.02(7) . ?
O9 C8 1.231(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.510(3) . ?
C7 C6 1.553(3) . ?
C12 C11 1.526(3) . ?
C4 H4A 0.9300 . ?
C4 C3 1.355(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(3) . ?
C3 H3 0.9300 . ?
C6 H6A 0.9800 . ?
C6 C5 1.529(3) . ?
C11 H11 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
C12 O4 H4 109.5 . . ?
C11 O3 C6 111.95(14) . . ?
C10 O6 H6 109.5 . . ?
C1 N1 H1 119.5 . . ?
C1 N1 C4 121.0(2) . . ?
C4 N1 H1 119.5 . . ?
C2 N3 C1 117.0(2) . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
C7 C9 H9 111.3 . . ?
C10 C9 H9 111.3 . . ?
C10 C9 C7 112.13(16) . . ?
C10 C9 C11 108.76(17) . . ?
C11 C9 H9 111.3 . . ?
C11 C9 C7 101.56(15) . . ?
C8 O8 H8 112(3) . . ?
N3 C1 N1 121.6(2) . . ?
N2 C1 N1 119.4(2) . . ?
N2 C1 N3 119.1(2) . . ?
C9 C7 H7 108.4 . . ?
C9 C7 C6 103.82(15) . . ?
C8 C7 C9 115.97(16) . . ?
C8 C7 H7 108.4 . . ?
C8 C7 C6 111.47(16) . . ?
C6 C7 H7 108.4 . . ?
O6 C10 C9 112.63(19) . . ?
O7 C10 O6 124.9(2) . . ?
O7 C10 C9 122.47(19) . . ?
O8 C8 C7 118.50(18) . . ?
O9 C8 O8 123.54(19) . . ?
O9 C8 C7 117.77(18) . . ?
O4 C12 C11 118.35(18) . . ?
O5 C12 O4 121.3(2) . . ?
O5 C12 C11 120.3(2) . . ?
N1 C4 H4A 120.3 . . ?
N1 C4 C3 119.5(2) . . ?
C3 C4 H4A 120.3 . . ?
N3 C2 H2 118.0 . . ?
N3 C2 C3 124.0(2) . . ?
C3 C2 H2 118.0 . . ?
C4 C3 C2 116.9(2) . . ?
C4 C3 H3 121.5 . . ?
C2 C3 H3 121.5 . . ?
O3 C6 C7 106.24(14) . . ?
O3 C6 H6A 110.0 . . ?
O3 C6 C5 109.21(15) . . ?
C7 C6 H6A 110.0 . . ?
C5 C6 C7 111.29(17) . . ?
C5 C6 H6A 110.0 . . ?
O3 C11 C9 106.94(15) . . ?
O3 C11 C12 111.59(16) . . ?
O3 C11 H11 108.4 . . ?
C9 C11 H11 108.4 . . ?
C12 C11 C9 113.07(18) . . ?
C12 C11 H11 108.4 . . ?
O1 C5 C6 117.38(18) . . ?
O2 C5 O1 125.1(2) . . ?
O2 C5 C6 117.52(17) . . ?

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
O4 H4 O2 0.82 1.82 2.605(2) 160.3 . yes
O6 H6 O1 0.82 1.85 2.662(2) 172.5 2_655 yes
N1 H1 O1 0.86 1.86 2.711(2) 170.0 . yes
N2 H2B O2 0.86 1.99 2.853(2) 177.6 . yes
O8 H8 O9 1.02(7) 1.66(7) 2.676(3) 176(6) 3_666 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
O4 C12 C11 O3 -13.8(3) . . . . ?
O4 C12 C11 C9 106.8(2) . . . . ?
O3 C6 C5 O1 -152.7(2) . . . . ?
O3 C6 C5 O2 29.2(3) . . . . ?
N1 C4 C3 C2 0.6(4) . . . . ?
N3 C2 C3 C4 0.2(4) . . . . ?
C9 C7 C8 O8 -22.7(3) . . . . ?
C9 C7 C8 O9 162.2(2) . . . . ?
C9 C7 C6 O3 19.5(2) . . . . ?
C9 C7 C6 C5 138.28(16) . . . . ?
O5 C12 C11 O3 164.1(2) . . . . ?
O5 C12 C11 C9 -75.3(3) . . . . ?
C1 N1 C4 C3 -1.1(4) . . . . ?
C1 N3 C2 C3 -0.3(4) . . . . ?
C7 C9 C10 O6 130.12(18) . . . . ?
C7 C9 C10 O7 -51.6(3) . . . . ?
C7 C9 C11 O3 29.4(2) . . . . ?
C7 C9 C11 C12 -93.86(18) . . . . ?
C7 C6 C5 O1 90.3(2) . . . . ?
C7 C6 C5 O2 -87.8(2) . . . . ?
C10 C9 C7 C8 -35.5(2) . . . . ?
C10 C9 C7 C6 87.10(19) . . . . ?
C10 C9 C11 O3 -89.04(18) . . . . ?
C10 C9 C11 C12 147.74(17) . . . . ?
C8 C7 C6 O3 145.05(17) . . . . ?
C8 C7 C6 C5 -96.18(19) . . . . ?
C4 N1 C1 N3 1.0(4) . . . . ?
C4 N1 C1 N2 -179.3(3) . . . . ?
C2 N3 C1 N1 -0.2(4) . . . . ?
C2 N3 C1 N2 -180.0(3) . . . . ?
C6 O3 C11 C9 -18.4(2) . . . . ?
C6 O3 C11 C12 105.70(18) . . . . ?
C6 C7 C8 O8 -141.2(2) . . . . ?
C6 C7 C8 O9 43.7(3) . . . . ?
C11 O3 C6 C7 -0.9(2) . . . . ?
C11 O3 C6 C5 -121.05(18) . . . . ?
C11 C9 C7 C8 -151.46(19) . . . . ?
C11 C9 C7 C6 -28.85(19) . . . . ?
C11 C9 C10 O6 -118.37(19) . . . . ?
C11 C9 C10 O7 59.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
