#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2225308.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_2225308
loop_
_publ_author_name
'Ebenezer, Samuel'
'Muthiah, Packianathan Thomas'
_publ_section_title
;
 2-Amino-4,6-dimethylpyrimidine--anthranilic acid (1/1)
;
_journal_coeditor_code           KP2248
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o516
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C6 H9 N3, C7 H7 N O2'
_chemical_formula_moiety         'C6 H9 N3, C7 H7 N O2'
_chemical_formula_sum            'C13 H16 N4 O2'
_chemical_formula_weight         260.30
_chemical_name_common
'2-amino-4,6-dimethylpyrimidine-anthranilic acid'
_chemical_name_systematic
;
2-amino-4,6-dimethylpyrimidine--anthranilic acid (1/1)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                77.5830(10)
_cell_angle_beta                 78.9900(10)
_cell_angle_gamma                82.4730(10)
_cell_formula_units_Z            2
_cell_length_a                   7.1922(2)
_cell_length_b                   7.4269(2)
_cell_length_c                   13.0675(3)
_cell_measurement_reflns_used    4279
_cell_measurement_temperature    293
_cell_measurement_theta_max      31.3
_cell_measurement_theta_min      1.6
_cell_volume                     666.18(3)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_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  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16171
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        31.31
_diffrn_reflns_theta_max         31.31
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         4279
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0730
_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^)+(0.0991P)^2^+0.0554P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1744
_reflns_number_gt                3021
_reflns_number_total             4279
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    kp2248.cif
_[local]_cod_data_source_block   I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        666.19(3)
_cod_database_code               2225308
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
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
N1 0.0312(4) 0.0465(5) 0.0358(5) 0.0002(4) -0.0026(3) -0.0059(4)
N2 0.0341(5) 0.0840(8) 0.0344(5) 0.0112(5) -0.0005(4) -0.0018(5)
N3 0.0305(4) 0.0512(5) 0.0450(5) 0.0019(4) -0.0010(4) -0.0073(4)
C2 0.0306(5) 0.0491(6) 0.0368(5) 0.0006(4) -0.0025(4) -0.0073(4)
C4 0.0325(5) 0.0406(5) 0.0537(7) 0.0012(4) -0.0077(5) -0.0084(5)
C5 0.0404(6) 0.0455(6) 0.0501(7) 0.0025(5) -0.0125(5) -0.0016(5)
C6 0.0387(5) 0.0410(5) 0.0403(6) -0.0029(4) -0.0069(4) -0.0043(4)
C7 0.0544(7) 0.0623(8) 0.0406(6) -0.0004(6) -0.0029(5) 0.0001(5)
C8 0.0343(6) 0.0600(8) 0.0762(9) 0.0086(5) -0.0082(6) -0.0089(7)
O1 0.0348(4) 0.0706(6) 0.0412(5) 0.0105(4) -0.0062(3) 0.0000(4)
O2 0.0427(5) 0.0916(7) 0.0414(5) 0.0189(5) 0.0008(4) 0.0043(4)
N4 0.0513(6) 0.0679(7) 0.0395(5) 0.0100(5) -0.0121(5) 0.0012(5)
C9 0.0341(5) 0.0442(6) 0.0384(5) 0.0016(4) -0.0052(4) -0.0037(4)
C10 0.0319(5) 0.0371(5) 0.0372(5) 0.0010(4) -0.0053(4) -0.0040(4)
C11 0.0395(6) 0.0476(6) 0.0392(6) 0.0032(5) -0.0053(5) -0.0032(4)
C12 0.0421(6) 0.0576(7) 0.0483(7) 0.0027(5) 0.0037(5) -0.0094(5)
C13 0.0353(6) 0.0558(7) 0.0657(8) 0.0078(5) -0.0039(5) -0.0142(6)
C14 0.0400(6) 0.0522(7) 0.0571(7) 0.0081(5) -0.0152(5) -0.0082(5)
C15 0.0392(5) 0.0387(5) 0.0428(6) 0.0024(4) -0.0100(4) -0.0054(4)
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N1 0.27302(13) 0.63647(13) 0.24381(7) 0.0389(3) Uani . . 1.000
N N2 0.24994(14) 0.50645(17) 0.42161(8) 0.0546(4) Uani . . 1.000
N N3 -0.01789(13) 0.67010(14) 0.36590(8) 0.0438(3) Uani . . 1.000
C C2 0.16646(15) 0.60562(16) 0.34206(9) 0.0398(3) Uani . . 1.000
C C4 -0.09918(16) 0.77159(16) 0.28620(10) 0.0428(3) Uani . . 1.000
C C5 -0.00014(17) 0.80839(17) 0.18345(10) 0.0465(4) Uani . . 1.000
C C6 0.18851(16) 0.73870(15) 0.16483(9) 0.0406(3) Uani . . 1.000
C C7 0.3091(2) 0.7734(2) 0.05754(10) 0.0551(4) Uani . . 1.000
C C8 -0.30286(18) 0.8452(2) 0.31434(13) 0.0589(4) Uani . . 1.000
O O1 0.62794(12) 0.47921(13) 0.18713(7) 0.0520(3) Uani . . 1.000
O O2 0.62400(13) 0.35172(16) 0.35704(7) 0.0646(3) Uani . . 1.000
N N4 0.94272(18) 0.17934(18) 0.41965(9) 0.0555(3) Uani . . 1.000
C C9 0.70902(15) 0.38005(16) 0.26562(9) 0.0402(3) Uani . . 1.000
C C10 0.90843(15) 0.30730(14) 0.23577(8) 0.0364(3) Uani . . 1.000
C C11 0.99344(17) 0.33560(16) 0.12857(9) 0.0438(3) Uani . . 1.000
C C12 1.18091(18) 0.27621(19) 0.09731(11) 0.0517(4) Uani . . 1.000
C C13 1.28729(18) 0.18659(19) 0.17468(12) 0.0536(4) Uani . . 1.000
C C14 1.20848(18) 0.15583(18) 0.27979(11) 0.0503(4) Uani . . 1.000
C C15 1.01624(16) 0.21446(15) 0.31397(9) 0.0408(3) Uani . . 1.000
H H2A 0.18650 0.48560 0.48510 0.0650 Uiso . R 1.000
H H2B 0.36720 0.46320 0.40940 0.0650 Uiso . R 1.000
H H5 -0.05890 0.87820 0.12830 0.0560 Uiso calc R 1.000
H H7A 0.23640 0.85160 0.00780 0.0830 Uiso calc R 1.000
H H7B 0.35080 0.65770 0.03500 0.0830 Uiso calc R 1.000
H H7C 0.41780 0.83320 0.06070 0.0830 Uiso calc R 1.000
H H8A -0.36050 0.87650 0.25150 0.0710 Uiso calc R 1.000
H H8B -0.30820 0.95370 0.34400 0.0710 Uiso calc R 1.000
H H8C -0.37030 0.75250 0.36550 0.0710 Uiso calc R 1.000
H H1 0.51810 0.51100 0.20940 0.0780 Uiso . R 1.000
H H4A 0.820(3) 0.238(3) 0.4358(16) 0.088(6) Uiso . . 1.000
H H4B 1.032(3) 0.151(3) 0.4607(16) 0.093(6) Uiso . . 1.000
H H11 0.92120 0.39610 0.07720 0.0530 Uiso calc R 1.000
H H12 1.23520 0.29570 0.02580 0.0620 Uiso calc R 1.000
H H13 1.41450 0.14680 0.15460 0.0640 Uiso calc R 1.000
H H14 1.28300 0.09490 0.32990 0.0600 Uiso calc R 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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
_geom_angle_publ_flag
C9 O1 H1 110.00 no
C2 N1 C6 117.21(10) no
C2 N3 C4 116.98(10) no
C2 N2 H2A 120.00 no
C2 N2 H2B 120.00 no
H2A N2 H2B 120.00 no
H4A N4 H4B 127.5(19) no
C15 N4 H4B 112.9(13) no
C15 N4 H4A 113.4(12) no
N1 C2 N3 124.84(10) no
N1 C2 N2 117.74(10) no
N2 C2 N3 117.42(10) no
N3 C4 C8 116.34(11) no
N3 C4 C5 121.65(11) no
C5 C4 C8 122.01(12) no
C4 C5 C6 118.28(11) no
N1 C6 C7 116.38(11) no
C5 C6 C7 122.59(11) no
N1 C6 C5 121.03(11) no
C6 C5 H5 121.00 no
C4 C5 H5 121.00 no
C6 C7 H7B 109.00 no
C6 C7 H7C 109.00 no
C6 C7 H7A 109.00 no
H7A C7 H7B 109.00 no
H7A C7 H7C 109.00 no
H7B C7 H7C 109.00 no
C4 C8 H8B 109.00 no
C4 C8 H8C 109.00 no
H8A C8 H8B 109.00 no
C4 C8 H8A 109.00 no
H8A C8 H8C 109.00 no
H8B C8 H8C 109.00 no
O2 C9 C10 122.73(11) no
O1 C9 O2 121.75(11) no
O1 C9 C10 115.52(10) no
C9 C10 C15 120.80(10) no
C11 C10 C15 119.51(10) no
C9 C10 C11 119.66(10) no
C10 C11 C12 121.70(11) no
C11 C12 C13 118.63(12) no
C12 C13 C14 121.14(13) no
C13 C14 C15 121.38(12) no
N4 C15 C14 119.47(11) no
C10 C15 C14 117.64(11) no
N4 C15 C10 122.90(11) no
C10 C11 H11 119.00 no
C12 C11 H11 119.00 no
C11 C12 H12 121.00 no
C13 C12 H12 121.00 no
C12 C13 H13 119.00 no
C14 C13 H13 119.00 no
C13 C14 H14 119.00 no
C15 C14 H14 119.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C9 1.3136(15) no
O2 C9 1.2214(14) no
O1 H1 0.8100 no
N1 C6 1.3390(15) no
N1 C2 1.3535(14) no
N2 C2 1.3330(16) no
N3 C4 1.3320(16) no
N3 C2 1.3507(15) no
N2 H2B 0.8600 no
N2 H2A 0.8600 no
N4 C15 1.3627(16) no
N4 H4A 0.94(2) no
N4 H4B 0.89(2) no
C4 C8 1.5003(18) no
C4 C5 1.3830(18) no
C5 C6 1.3828(17) no
C6 C7 1.4910(17) no
C5 H5 0.9300 no
C7 H7A 0.9600 no
C7 H7C 0.9600 no
C7 H7B 0.9600 no
C8 H8C 0.9600 no
C8 H8B 0.9600 no
C8 H8A 0.9600 no
C9 C10 1.4748(16) no
C10 C15 1.4073(16) no
C10 C11 1.4001(15) no
C11 C12 1.3750(18) no
C12 C13 1.387(2) no
C13 C14 1.364(2) no
C14 C15 1.4110(18) no
C11 H11 0.9300 no
C12 H12 0.9300 no
C13 H13 0.9300 no
C14 H14 0.9300 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C7 3.3882(17) . no
O1 N1 2.7014(13) . no
O2 N4 2.6571(17) . no
O2 N2 2.8303(15) . no
O1 H11 2.4000 . no
O2 H2B 1.9800 . no
O2 H4A 1.91(2) . no
N1 O1 2.7014(13) . no
N2 N3 3.0745(14) 2_566 no
N2 O2 2.8303(15) . no
N3 N2 3.0745(14) 2_566 no
N4 N4 3.1409(18) 2_756 no
N4 O2 2.6571(17) . no
N1 H1 1.9000 . no
N2 H4A 2.87(2) 2_666 no
N3 H2A 2.2600 2_566 no
N3 H4B 2.84(2) 2_666 no
N4 H4B 2.62(2) 2_756 no
C2 C15 3.3428(16) 1_455 no
C2 C14 3.5670(18) 1_455 no
C4 C9 3.4584(17) 1_455 no
C6 C13 3.5249(18) 1_465 no
C7 O1 3.3882(17) . no
C9 C4 3.4584(17) 1_655 no
C13 C6 3.5249(18) 1_645 no
C14 C2 3.5670(18) 1_655 no
C15 C2 3.3428(16) 1_655 no
C2 H1 2.8800 . no
C2 H2A 3.1000 2_566 no
C6 H1 2.8100 . no
C7 H13 3.0800 2_765 no
C7 H1 2.9500 . no
C9 H4A 2.48(2) . no
C9 H2B 2.8800 . no
C11 H11 2.9900 2_765 no
C12 H11 3.0700 2_765 no
H1 C7 2.9500 . no
H1 H2B 2.6000 . no
H1 C6 2.8100 . no
H1 N1 1.9000 . no
H1 C2 2.8800 . no
H2A H4A 2.4800 2_666 no
H2A N3 2.2600 2_566 no
H2A C2 3.1000 2_566 no
H2B C9 2.8800 . no
H2B H1 2.6000 . no
H2B O2 1.9800 . no
H4A H2A 2.4800 2_666 no
H4A O2 1.91(2) . no
H4A C9 2.48(2) . no
H4A N2 2.87(2) 2_666 no
H4B N4 2.62(2) 2_756 no
H4B H4B 2.32(3) 2_756 no
H4B N3 2.84(2) 2_666 no
H4B H14 2.3000 . no
H5 H7A 2.4000 . no
H5 H8A 2.4400 . no
H7A H5 2.4000 . no
H8A H5 2.4400 . no
H11 O1 2.4000 . no
H11 C11 2.9900 2_765 no
H11 C12 3.0700 2_765 no
H11 H11 2.4500 2_765 no
H13 C7 3.0800 2_765 no
H14 H4B 2.3000 . no
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
_geom_hbond_publ_flag
O1 H1 N1 . 0.8100 1.9000 2.7014(13) 168.00 yes
N2 H2A N3 2_566 0.8600 2.2600 3.0745(14) 159.00 yes
N2 H2B O2 . 0.8600 1.9800 2.8303(15) 169.00 yes
N4 H4A O2 . 0.94(2) 1.91(2) 2.6571(17) 135.5(17) yes
N4 H4B N4 2_756 0.89(2) 2.62(2) 3.1409(18) 118.7(17) yes
C11 H11 O1 . 0.9300 2.4000 2.7353(15) 101.00 no
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_publ_flag
C6 N1 C2 N2 -178.98(11) no
C6 N1 C2 N3 0.06(17) no
C2 N1 C6 C5 -0.37(17) no
C2 N1 C6 C7 179.13(11) no
C4 N3 C2 N1 -0.10(18) no
C4 N3 C2 N2 178.93(11) no
C2 N3 C4 C5 0.47(17) no
C2 N3 C4 C8 -178.87(11) no
N3 C4 C5 C6 -0.78(19) no
C8 C4 C5 C6 178.53(12) no
C4 C5 C6 N1 0.72(18) no
C4 C5 C6 C7 -178.75(12) no
O1 C9 C10 C11 -4.29(16) no
O1 C9 C10 C15 173.81(10) no
O2 C9 C10 C11 176.12(12) no
O2 C9 C10 C15 -5.78(18) no
C9 C10 C11 C12 177.60(12) no
C15 C10 C11 C12 -0.53(18) no
C9 C10 C15 N4 2.90(18) no
C9 C10 C15 C14 -177.28(11) no
C11 C10 C15 N4 -178.99(12) no
C11 C10 C15 C14 0.83(16) no
C10 C11 C12 C13 -0.2(2) no
C11 C12 C13 C14 0.6(2) no
C12 C13 C14 C15 -0.3(2) no
C13 C14 C15 N4 179.37(13) no
C13 C14 C15 C10 -0.45(19) no