#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2222233.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_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       '\f and \w 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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0352P)^2^+0.0120P] where P=(Fo^2^+2Fc^2^)/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>2\s(I)
_[local]_cod_data_source_file    bi2374.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_database_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
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_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0593(11) 0.0969(15) 0.0473(11) 0.0084(10) 0.0053(9) -0.0141(10)
O2 0.0568(12) 0.1232(16) 0.0564(12) 0.0167(11) 0.0055(9) -0.0012(10)
N1 0.0425(11) 0.0546(12) 0.0480(12) -0.0031(9) 0.0092(9) -0.0005(9)
N2 0.0584(13) 0.0594(13) 0.0510(13) -0.0063(10) 0.0179(10) -0.0042(11)
N3 0.0552(13) 0.0919(16) 0.0472(13) 0.0168(11) 0.0084(10) -0.0057(11)
C1 0.0620(17) 0.0566(15) 0.0439(15) -0.0070(13) 0.0109(12) 0.0003(12)
C2 0.0670(19) 0.0707(18) 0.0617(17) -0.0002(14) 0.0157(14) -0.0015(14)
C3 0.081(2) 0.085(2) 0.080(2) 0.0071(17) 0.0337(18) -0.0012(18)
C4 0.119(3) 0.073(2) 0.078(2) -0.003(2) 0.056(2) -0.0027(18)
C5 0.119(3) 0.113(3) 0.0486(19) -0.020(2) 0.0181(18) -0.0134(17)
C6 0.0767(19) 0.098(2) 0.0513(17) -0.0100(16) 0.0084(14) -0.0062(16)
C7 0.0529(16) 0.0653(17) 0.0448(16) -0.0014(13) 0.0080(13) 0.0025(12)
C8 0.0524(15) 0.0516(14) 0.0456(15) -0.0068(12) 0.0121(12) -0.0030(12)
C9 0.0502(15) 0.0550(16) 0.0516(16) -0.0112(12) 0.0041(12) 0.0032(12)
C10 0.0705(19) 0.0703(17) 0.0454(16) -0.0090(15) 0.0058(13) 0.0030(13)
C11 0.0694(18) 0.0566(16) 0.0486(16) -0.0128(14) 0.0196(13) -0.0031(12)
C12 0.0561(17) 0.0836(18) 0.0700(18) 0.0001(14) 0.0004(13) 0.0025(15)
C13 0.100(2) 0.0828(19) 0.0562(17) -0.0108(17) 0.0289(15) -0.0094(15)
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
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_distance
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
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)