#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/73/7217327.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_7217327
loop_
_publ_author_name
'Orvay, Francisca'
'Bauzá, Antonio'
'Barceló-Oliver, Miquel'
'García-Raso, Angel'
'Fiol, Joan J.'
'Costa, Antoni'
'Molins, Elies'
'Mata, Ignasi'
'Frontera, Antonio'
_publ_section_title
;
 Synthesis, X-ray characterization and DFT studies of
 bis-N-imidazolylpyrimidine salts: the prominent role of hydrogen bonding
 and anion--π interactions
;
_journal_issue                   38
_journal_name_full               CrystEngComm
_journal_page_first              9043
_journal_paper_doi               10.1039/C4CE01425A
_journal_volume                  16
_journal_year                    2014
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C10 H10 N6, 2(N O3), H N O3'
_chemical_formula_sum            'C10 H11 N9 O9'
_chemical_formula_weight         401.28
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2013-08-21T18:18:30-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 92.794(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5097(19)
_cell_length_b                   11.521(3)
_cell_length_c                   14.622(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      21.4
_cell_measurement_theta_min      8
_cell_measurement_wavelength     0.71073
_cell_volume                     1600.1(6)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled ω scans'
_diffrn_orient_matrix_type
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      0.042593
_diffrn_orient_matrix_UB_12      0.079103
_diffrn_orient_matrix_UB_13      -0.002996
_diffrn_orient_matrix_UB_21      0.095551
_diffrn_orient_matrix_UB_22      -0.035502
_diffrn_orient_matrix_UB_23      -0.002777
_diffrn_orient_matrix_UB_31      -0.010972
_diffrn_orient_matrix_UB_32      -0.001974
_diffrn_orient_matrix_UB_33      -0.068406
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2818
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.25
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        63
_diffrn_standards_interval_count 66
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  0.9696
_exptl_absorpt_correction_T_min  0.4244
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
        Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         2818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0733P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1459
_reflns_number_gt                1759
_reflns_number_total             2818
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce01425a2.cif
_cod_data_source_block           pm190
_cod_depositor_comments
'Adding full bibliography for 7217324--7217328.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7217327
loop_
_symmetry_equiv_pos_as_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'
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_symmetry_multiplicity
_atom_site_calc_flag
C2 C 0.0377(4) 0.1567(3) 0.4156(2) 0.0406(8) Uani 1 1 d
C4 C -0.1831(3) 0.1101(3) 0.4367(2) 0.0420(8) Uani 1 1 d
C5 C -0.1669(3) 0.1172(3) 0.3460(2) 0.0389(8) Uani 1 1 d
C6 C 0.0385(3) 0.1616(2) 0.24881(18) 0.0327(7) Uani 1 1 d
C8 C 0.2379(3) 0.1920(3) 0.1768(2) 0.0450(9) Uani 1 1 d
C10 C 0.0419(3) 0.1637(2) 0.09059(19) 0.0322(7) Uani 1 1 d
C11 C -0.0372(3) 0.1519(3) 0.1670(2) 0.0345(7) Uani 1 1 d
C13 C 0.0500(4) 0.1584(3) -0.07659(19) 0.0390(8) Uani 1 1 d
C15 C -0.1689(4) 0.1169(3) -0.1155(2) 0.0413(8) Uani 1 1 d
C16 C -0.1588(3) 0.1232(3) -0.0244(2) 0.0373(8) Uani 1 1 d
N1 N -0.0287(2) 0.1470(2) 0.33365(15) 0.0324(6) Uani 1 1 d
N2 N -0.3503(3) 0.3355(2) 0.16977(17) 0.0396(7) Uani 1 1 d
N3 N -0.0540(3) 0.1343(2) 0.47825(17) 0.0407(7) Uani 1 1 d
N4 N -0.4237(3) -0.0351(3) 0.13265(18) 0.0484(7) Uani 1 1 d
N5 N -0.5987(3) 0.0354(3) 0.3797(2) 0.0542(8) Uani 1 1 d
N7 N 0.1750(2) 0.1803(2) 0.25695(16) 0.0393(7) Uani 1 1 d
N9 N 0.1783(3) 0.1844(2) 0.09396(16) 0.0395(7) Uani 1 1 d
N12 N -0.0205(2) 0.14937(19) 0.00098(15) 0.0307(6) Uani 1 1 d
N14 N -0.0385(3) 0.1396(2) -0.14613(17) 0.0418(7) Uani 1 1 d
O1 O -0.2933(2) 0.3172(2) 0.09688(14) 0.0554(7) Uani 1 1 d
O2 O -0.2860(2) 0.3293(2) 0.24418(15) 0.0620(7) Uani 1 1 d
O3 O -0.4810(2) 0.3637(2) 0.16711(13) 0.0472(6) Uani 1 1 d
O4 O -0.3604(3) 0.0565(2) 0.14848(16) 0.0688(8) Uani 1 1 d
O5 O -0.4015(3) -0.0963(2) 0.06734(18) 0.0800(9) Uani 1 1 d
O6 O -0.5177(2) -0.0667(2) 0.18832(16) 0.0581(7) Uani 1 1 d
O7 O -0.6779(3) -0.0436(2) 0.35877(18) 0.0796(9) Uani 1 1 d
O8 O -0.5009(2) 0.0646(2) 0.32257(17) 0.0644(8) Uani 1 1 d
O9 O -0.6033(3) 0.0935(2) 0.44834(18) 0.0808(9) Uani 1 1 d
H2 H 0.126(3) 0.181(3) 0.428(2) 0.057(11) Uiso 1 1 d
H3 H -0.033(3) 0.139(2) 0.540(2) 0.052(10) Uiso 1 1 d
H4 H -0.273(4) 0.094(3) 0.468(3) 0.077(11) Uiso 1 1 d
H5 H -0.240(3) 0.113(2) 0.300(2) 0.035(8) Uiso 1 1 d
H8 H 0.335(3) 0.210(2) 0.1866(18) 0.040(8) Uiso 1 1 d
H11 H -0.122(3) 0.146(2) 0.161(2) 0.037(9) Uiso 1 1 d
H13 H 0.137(3) 0.178(2) -0.0712(19) 0.033(9) Uiso 1 1 d
H14 H -0.012(4) 0.142(3) -0.207(3) 0.084(13) Uiso 1 1 d
H15 H -0.248(3) 0.110(2) -0.153(2) 0.042(9) Uiso 1 1 d
H16 H -0.217(3) 0.120(3) 0.015(2) 0.048(9) Uiso 1 1 d
H8N H -0.510(4) 0.006(4) 0.270(3) 0.114(16) Uiso 1 1 d
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 -4 0
5 -3 0
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N3 C2 N1 107.9(3)
N3 C2 H2 125(2)
N1 C2 H2 127(2)
C5 C4 N3 106.3(3)
C5 C4 H4 127(2)
N3 C4 H4 127(2)
C4 C5 N1 107.4(3)
C4 C5 H5 125.6(17)
N1 C5 H5 126.4(17)
N7 C6 C11 124.5(3)
N7 C6 N1 114.9(3)
C11 C6 N1 120.6(3)
N9 C8 N7 127.2(3)
N9 C8 H8 121.7(16)
N7 C8 H8 111.1(16)
N9 C10 C11 124.1(3)
N9 C10 N12 114.9(2)
C11 C10 N12 120.9(3)
C6 C11 C10 114.4(3)
C6 C11 H11 125(2)
C10 C11 H11 120(2)
N14 C13 N12 108.3(3)
N14 C13 H13 134.2(19)
N12 C13 H13 117.4(19)
C16 C15 N14 107.2(3)
C16 C15 H15 128.8(18)
N14 C15 H15 123.4(18)
C15 C16 N12 107.5(3)
C15 C16 H16 133(2)
N12 C16 H16 119(2)
C2 N1 C5 108.4(2)
C2 N1 C6 123.9(3)
C5 N1 C6 127.6(2)
O2 N2 O1 122.4(3)
O2 N2 O3 118.9(2)
O1 N2 O3 118.8(3)
C2 N3 C4 109.9(3)
C2 N3 H3 123.7(19)
C4 N3 H3 126.4(19)
O5 N4 O4 122.9(3)
O5 N4 O6 119.0(3)
O4 N4 O6 118.1(3)
O9 N5 O7 125.3(3)
O9 N5 O8 116.0(3)
O7 N5 O8 118.6(3)
C6 N7 C8 114.5(3)
C8 N9 C10 115.2(2)
C13 N12 C16 107.3(3)
C13 N12 C10 124.3(3)
C16 N12 C10 128.4(2)
C13 N14 C15 109.7(3)
C13 N14 H14 123(2)
C15 N14 H14 128(2)
N4 O6 H8N 110.0(16)
N5 O8 H8N 106(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 N3 1.321(4)
C2 N1 1.332(4)
C2 H2 0.90(3)
C4 C5 1.346(4)
C4 N3 1.371(4)
C4 H4 1.00(3)
C5 N1 1.378(4)
C5 H5 0.94(3)
C6 N7 1.316(3)
C6 C11 1.370(4)
C6 N1 1.433(3)
C8 N9 1.314(4)
C8 N7 1.348(4)
C8 H8 0.95(3)
C10 N9 1.317(3)
C10 C11 1.384(4)
C10 N12 1.422(4)
C11 H11 0.81(3)
C13 N14 1.306(4)
C13 N12 1.349(3)
C13 H13 0.86(3)
C15 C16 1.333(4)
C15 N14 1.364(4)
C15 H15 0.92(3)
C16 N12 1.382(4)
C16 H16 0.82(3)
N2 O2 1.224(3)
N2 O1 1.237(3)
N2 O3 1.284(3)
N3 H3 0.92(3)
N4 O5 1.214(3)
N4 O4 1.232(3)
N4 O6 1.291(3)
N5 O9 1.209(3)
N5 O7 1.211(4)
N5 O8 1.323(3)
N14 H14 0.93(4)
O6 H8N 1.45(5)
O8 H8N 1.03(4)
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
N3 H3 O3 0.92(3) 1.90(3) 2.815(3) 175(3) 4_666
N3 H3 O1 0.92(3) 2.44(3) 3.009(4) 120(2) 4_666
N3 H3 N2 0.92(3) 2.53(3) 3.345(4) 149(2) 4_666
N14 H14 O3 0.93(4) 1.88(4) 2.811(3) 172(3) 4_665
N14 H14 O2 0.93(4) 2.32(3) 2.974(3) 127(3) 4_665
N14 H14 N2 0.93(4) 2.44(4) 3.317(3) 156(3) 4_665
O8 H8N O6 1.03(4) 1.45(5) 2.477(3) 174(4) .
O8 H8N N4 1.03(4) 2.25(4) 3.125(4) 142(3) .
O8 H8N O4 1.03(4) 2.40(4) 2.934(3) 112(3) .
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
N3 C4 C5 N1 -0.7(4)
N7 C6 C11 C10 -0.2(5)
N1 C6 C11 C10 -177.7(2)
N9 C10 C11 C6 -1.0(4)
N12 C10 C11 C6 176.5(3)
N14 C15 C16 N12 -0.4(4)
N3 C2 N1 C5 0.0(3)
N3 C2 N1 C6 -178.0(3)
C4 C5 N1 C2 0.5(4)
C4 C5 N1 C6 178.3(3)
N7 C6 N1 C2 3.2(4)
C11 C6 N1 C2 -179.0(3)
N7 C6 N1 C5 -174.3(3)
C11 C6 N1 C5 3.5(4)
N1 C2 N3 C4 -0.4(4)
C5 C4 N3 C2 0.7(4)
C11 C6 N7 C8 1.3(4)
N1 C6 N7 C8 178.9(3)
N9 C8 N7 C6 -1.5(5)
N7 C8 N9 C10 0.4(5)
C11 C10 N9 C8 0.9(4)
N12 C10 N9 C8 -176.7(3)
N14 C13 N12 C16 0.3(3)
N14 C13 N12 C10 179.6(2)
C15 C16 N12 C13 0.1(3)
C15 C16 N12 C10 -179.2(3)
N9 C10 N12 C13 -1.6(4)
C11 C10 N12 C13 -179.3(3)
N9 C10 N12 C16 177.6(3)
C11 C10 N12 C16 -0.1(4)
N12 C13 N14 C15 -0.5(4)
C16 C15 N14 C13 0.5(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139198997
