#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/22/2222233.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222233
loop_
_publ_author_name
'Meng, A-Lan'
'Huang, Jun-E'
'Zheng, Bin'
'Li, Zhen-Jiang'
_publ_section_title
;
 2-Amino-4,6-dimethylpyrimidine--benzoic acid (1/1)
;
_journal_coeditor_code           BI2374
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1595
_journal_paper_doi               10.1107/S1600536809020649
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C6 H9 N3, C7 H6 O2'
_chemical_formula_moiety         'C6 H9 N3, C7 H6 O2'
_chemical_formula_sum            'C13 H15 N3 O2'
_chemical_formula_weight         245.28
_chemical_name_systematic
;
2-Amino-4,6-dimethylpyrimidine--benzoic acid (1/1)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.360(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7019(9)
_cell_length_b                   7.6466(10)
_cell_length_c                   25.285(3)
_cell_measurement_reflns_used    167
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      1.61
_cell_volume                     1295.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.1044
_diffrn_reflns_av_sigmaI/netI    0.0841
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6594
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.61
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_correction_T_min  0.9845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.192
_refine_ls_extinction_coef       0.0077(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0352P)²+0.0120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1366
_reflns_number_gt                1228
_reflns_number_total             2273
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2374.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222233
_cod_database_fobs_code          2222233
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.6583(2) 0.6591(2) 0.41923(6) 0.0678(5) Uani d . 1 . .
H H1 0.5870 0.7100 0.4402 0.102 Uiso calc R 1 . .
O O2 0.3940(3) 0.6933(3) 0.36625(7) 0.0787(6) Uani d . 1 . .
N N1 0.4633(3) 0.7645(2) 0.50129(7) 0.0482(5) Uani d . 1 . .
N N2 0.1976(3) 0.9074(2) 0.54612(8) 0.0560(6) Uani d . 1 . .
N N3 0.1836(3) 0.8632(2) 0.45633(8) 0.0646(6) Uani d . 1 . .
H H3A 0.2332 0.8250 0.4275 0.078 Uiso calc R 1 . .
H H3B 0.0689 0.9137 0.4557 0.078 Uiso calc R 1 . .
C C1 0.6891(4) 0.5714(3) 0.33125(9) 0.0540(6) Uani d . 1 . .
C C2 0.8886(4) 0.5334(3) 0.34037(10) 0.0662(7) Uani d . 1 . .
H H2 0.9484 0.5593 0.3730 0.079 Uiso calc R 1 . .
C C3 0.9993(5) 0.4573(4) 0.30126(13) 0.0813(9) Uani d . 1 . .
H H3 1.1337 0.4326 0.3075 0.098 Uiso calc R 1 . .
C C4 0.9124(6) 0.4184(4) 0.25352(13) 0.0892(10) Uani d . 1 . .
H H4 0.9866 0.3641 0.2276 0.107 Uiso calc R 1 . .
C C5 0.7167(6) 0.4587(4) 0.24346(11) 0.0931(10) Uani d . 1 . .
H H5 0.6586 0.4332 0.2106 0.112 Uiso calc R 1 . .
C C6 0.6032(4) 0.5382(4) 0.28248(10) 0.0754(8) Uani d . 1 . .
H H6 0.4708 0.5683 0.2754 0.090 Uiso calc R 1 . .
C C7 0.5664(4) 0.6473(3) 0.37388(10) 0.0542(7) Uani d . 1 . .
C C8 0.2837(4) 0.8443(3) 0.50166(10) 0.0497(6) Uani d . 1 . .
C C9 0.5618(3) 0.7431(3) 0.54739(9) 0.0522(6) Uani d . 1 . .
C C10 0.4805(4) 0.8019(3) 0.59401(10) 0.0620(7) Uani d . 1 . .
H H10 0.5481 0.7868 0.6262 0.074 Uiso calc R 1 . .
C C11 0.2973(4) 0.8831(3) 0.59146(10) 0.0579(7) Uani d . 1 . .
C C12 0.7598(4) 0.6537(3) 0.54573(11) 0.0699(8) Uani d . 1 . .
H H12A 0.7401 0.5309 0.5397 0.105 Uiso calc R 1 . .
H H12B 0.8303 0.6706 0.5788 0.105 Uiso calc R 1 . .
H H12C 0.8361 0.7022 0.5176 0.105 Uiso calc R 1 . .
C C13 0.1975(4) 0.9484(3) 0.64045(10) 0.0793(9) Uani d . 1 . .
H H13A 0.1886 1.0737 0.6393 0.119 Uiso calc R 1 . .
H H13B 0.2743 0.9136 0.6712 0.119 Uiso calc R 1 . .
H H13C 0.0658 0.8996 0.6421 0.119 Uiso calc R 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O1 H1 . . 109.5 ?
C9 N1 C8 . . 118.13(19) ?
C11 N2 C8 . . 116.7(2) ?
C8 N3 H3A . . 120.0 ?
C8 N3 H3B . . 120.0 ?
H3A N3 H3B . . 120.0 ?
C6 C1 C2 . . 119.6(2) ?
C6 C1 C7 . . 119.7(2) ?
C2 C1 C7 . . 120.7(2) ?
C3 C2 C1 . . 120.3(3) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
C4 C3 C2 . . 120.1(3) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 120.3(3) ?
C3 C4 H4 . . 119.8 ?
C5 C4 H4 . . 119.8 ?
C4 C5 C6 . . 120.2(3) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C1 C6 C5 . . 119.4(3) ?
C1 C6 H6 . . 120.3 ?
C5 C6 H6 . . 120.3 ?
O2 C7 O1 . . 123.4(2) ?
O2 C7 C1 . . 122.4(2) ?
O1 C7 C1 . . 114.2(2) ?
N3 C8 N1 . . 118.5(2) ?
N3 C8 N2 . . 117.4(2) ?
N1 C8 N2 . . 124.1(2) ?
N1 C9 C10 . . 120.4(2) ?
N1 C9 C12 . . 116.9(2) ?
C10 C9 C12 . . 122.7(2) ?
C11 C10 C9 . . 118.4(2) ?
C11 C10 H10 . . 120.8 ?
C9 C10 H10 . . 120.8 ?
N2 C11 C10 . . 122.3(2) ?
N2 C11 C13 . . 116.1(3) ?
C10 C11 C13 . . 121.6(3) ?
C9 C12 H12A . . 109.5 ?
C9 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C9 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.292(3) ?
O1 H1 . 0.820 ?
O2 C7 . 1.218(3) ?
N1 C9 . 1.336(3) ?
N1 C8 . 1.350(3) ?
N2 C11 . 1.326(3) ?
N2 C8 . 1.364(3) ?
N3 C8 . 1.322(3) ?
N3 H3A . 0.860 ?
N3 H3B . 0.860 ?
C1 C6 . 1.372(3) ?
C1 C2 . 1.382(3) ?
C1 C7 . 1.489(3) ?
C2 C3 . 1.379(4) ?
C2 H2 . 0.930 ?
C3 C4 . 1.361(4) ?
C3 H3 . 0.930 ?
C4 C5 . 1.365(4) ?
C4 H4 . 0.930 ?
C5 C6 . 1.399(4) ?
C5 H5 . 0.930 ?
C6 H6 . 0.930 ?
C9 C10 . 1.385(3) ?
C9 C12 . 1.494(3) ?
C10 C11 . 1.376(3) ?
C10 H10 . 0.930 ?
C11 C13 . 1.507(3) ?
C12 H12A . 0.960 ?
C12 H12B . 0.960 ?
C12 H12C . 0.960 ?
C13 H13A . 0.960 ?
C13 H13B . 0.960 ?
C13 H13C . 0.960 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 N1 . 0.82 1.82 2.606(2) 160
N3 H3A O2 . 0.86 2.16 3.003(3) 168
N3 H3B N2 3_576 0.86 2.25 3.098(3) 169
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -2.1(4) ?
C7 C1 C2 C3 . . . . 177.7(2) ?
C1 C2 C3 C4 . . . . -0.3(4) ?
C2 C3 C4 C5 . . . . 1.8(5) ?
C3 C4 C5 C6 . . . . -0.9(5) ?
C2 C1 C6 C5 . . . . 3.0(4) ?
C7 C1 C6 C5 . . . . -176.8(2) ?
C4 C5 C6 C1 . . . . -1.5(4) ?
C6 C1 C7 O2 . . . . -5.3(4) ?
C2 C1 C7 O2 . . . . 175.0(2) ?
C6 C1 C7 O1 . . . . 174.4(2) ?
C2 C1 C7 O1 . . . . -5.3(3) ?
C9 N1 C8 N3 . . . . -178.84(19) ?
C9 N1 C8 N2 . . . . 1.2(3) ?
C11 N2 C8 N3 . . . . 178.20(19) ?
C11 N2 C8 N1 . . . . -1.8(3) ?
C8 N1 C9 C10 . . . . -0.1(3) ?
C8 N1 C9 C12 . . . . 179.75(19) ?
N1 C9 C10 C11 . . . . -0.4(3) ?
C12 C9 C10 C11 . . . . 179.9(2) ?
C8 N2 C11 C10 . . . . 1.4(3) ?
C8 N2 C11 C13 . . . . -178.11(19) ?
C9 C10 C11 N2 . . . . -0.3(4) ?
C9 C10 C11 C13 . . . . 179.1(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655802
2 PubChem 139076756
