#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/38/2223808.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_2223808
loop_
_publ_author_name
'Lin, Cui-Hua'
'Liu, Nai-Sheng'
'Jian, Fang-Fang'
_publ_section_title
;
 2-Amino-4,6-dimethylpyrimidinium chloroacetate
;
_journal_coeditor_code           HB5174
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2913
_journal_paper_doi               10.1107/S1600536809044444
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C6 H10 N3 +, C2 H2 Cl O2 -'
_chemical_formula_moiety         'C6 H10 N3 +, C2 H2 Cl O2 -'
_chemical_formula_sum            'C8 H12 Cl N3 O2'
_chemical_formula_weight         217.66
_chemical_name_systematic
;
2-Amino-4,6-dimethylpyrimidinium chloroacetate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.90(3)
_cell_angle_beta                 96.53(3)
_cell_angle_gamma                91.15(3)
_cell_formula_units_Z            4
_cell_length_a                   4.4560(9)
_cell_length_b                   12.302(3)
_cell_length_c                   19.441(4)
_cell_measurement_reflns_used    3452
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.17
_cell_volume                     1057.1(4)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_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  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10303
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.341
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.428
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0546
_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)+(0.1056P)²+0.3945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1754
_refine_ls_wR_factor_ref         0.1952
_reflns_number_gt                3452
_reflns_number_total             4761
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5174.cif
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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_database_code               2223808
_cod_database_fobs_code          2223808
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl Cl1 0.92264(17) 0.01264(6) 0.17209(4) 0.0623(2) Uani d . 1 . .
O O4 0.7689(5) 0.14297(17) -0.00572(10) 0.0681(6) Uani d . 1 . .
C C16 0.8811(6) 0.13347(19) 0.05672(13) 0.0463(5) Uani d . 1 . .
O O3 1.0794(5) 0.19170(18) 0.08873(11) 0.0742(7) Uani d . 1 . .
C C15 0.7353(7) 0.0407(2) 0.09016(14) 0.0616(7) Uani d . 1 . .
H H15A 0.7320 -0.0243 0.0596 0.074 Uiso calc R 1 . .
H H15B 0.5276 0.0584 0.0954 0.074 Uiso calc R 1 . .
Cl Cl2 0.8148(2) 0.60659(7) 0.34169(5) 0.0862(3) Uani d . 1 . .
O O2 0.9854(5) 0.38470(15) 0.37047(10) 0.0594(5) Uani d . 1 . .
C C14 0.8160(6) 0.4192(2) 0.41493(13) 0.0497(6) Uani d . 1 . .
O O1 0.7445(6) 0.36870(18) 0.46320(12) 0.0798(7) Uani d . 1 . .
C C13 0.6862(8) 0.5308(2) 0.40795(16) 0.0632(7) Uani d . 1 . .
H H13A 0.7342 0.5722 0.4518 0.076 Uiso calc R 1 . .
H H13B 0.4680 0.5230 0.3993 0.076 Uiso calc R 1 . .
N N5 0.1724(4) 0.18552(15) 0.37450(10) 0.0418(4) Uani d . 1 . .
H H5A 0.1093 0.2511 0.3762 0.050 Uiso calc R 1 . .
N N6 0.1954(5) 0.01175(16) 0.42234(10) 0.0467(5) Uani d . 1 . .
C C10 0.1065(6) 0.11536(19) 0.42261(12) 0.0436(5) Uani d . 1 . .
C C9 0.4323(6) 0.0461(2) 0.32177(13) 0.0502(6) Uani d . 1 . .
H H9A 0.5446 0.0210 0.2870 0.060 Uiso calc R 1 . .
C C12 0.3572(6) -0.02223(19) 0.37232(13) 0.0477(5) Uani d . 1 . .
C C8 0.3363(5) 0.15178(19) 0.32440(12) 0.0430(5) Uani d . 1 . .
N N4 -0.0552(6) 0.15065(18) 0.47176(12) 0.0610(6) Uani d . 1 . .
H H4A -0.1012 0.1075 0.5026 0.073 Uiso calc R 1 . .
H H4B -0.1145 0.2167 0.4729 0.073 Uiso calc R 1 . .
C C7 0.4002(7) 0.2310(2) 0.27171(13) 0.0554(6) Uani d . 1 . .
H H7A 0.3149 0.2998 0.2829 0.083 Uiso calc R 1 . .
H H7B 0.3119 0.2038 0.2266 0.083 Uiso calc R 1 . .
H H7C 0.6146 0.2402 0.2718 0.083 Uiso calc R 1 . .
C C11 0.4550(8) -0.1383(2) 0.37303(18) 0.0689(8) Uani d . 1 . .
H H11A 0.3841 -0.1721 0.4118 0.103 Uiso calc R 1 . .
H H11B 0.6715 -0.1400 0.3770 0.103 Uiso calc R 1 . .
H H11C 0.3719 -0.1768 0.3308 0.103 Uiso calc R 1 . .
N N2 0.0615(5) 0.69331(16) 0.07225(10) 0.0457(5) Uani d . 1 . .
H H2A 0.1088 0.7470 0.0486 0.055 Uiso calc R 1 . .
N N3 -0.2359(5) 0.53279(17) 0.07940(11) 0.0489(5) Uani d . 1 . .
C C6 -0.0956(6) 0.5215(2) 0.14272(13) 0.0493(6) Uani d . 1 . .
N N1 -0.2951(5) 0.63311(18) -0.01745(11) 0.0566(6) Uani d . 1 . .
H H1A -0.4349 0.5876 -0.0354 0.068 Uiso calc R 1 . .
H H1B -0.2464 0.6878 -0.0401 0.068 Uiso calc R 1 . .
C C4 -0.1547(5) 0.61899(19) 0.04524(12) 0.0443(5) Uani d . 1 . .
C C2 0.2013(5) 0.6821(2) 0.13654(13) 0.0472(5) Uani d . 1 . .
C C3 0.1249(6) 0.5956(2) 0.17351(14) 0.0520(6) Uani d . 1 . .
H H3B 0.2183 0.5868 0.2181 0.062 Uiso calc R 1 . .
C C1 0.4302(6) 0.7682(2) 0.16441(15) 0.0594(7) Uani d . 1 . .
H H1C 0.4485 0.8204 0.1300 0.089 Uiso calc R 1 . .
H H1D 0.6220 0.7355 0.1759 0.089 Uiso calc R 1 . .
H H1E 0.3673 0.8039 0.2052 0.089 Uiso calc R 1 . .
C C5 -0.1883(8) 0.4234(2) 0.17923(16) 0.0657(8) Uani d . 1 . .
H H5B -0.3422 0.3821 0.1499 0.099 Uiso calc R 1 . .
H H5C -0.2654 0.4466 0.2216 0.099 Uiso calc R 1 . .
H H5D -0.0162 0.3788 0.1896 0.099 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'
Cl Cl 0.1484 0.1585 '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
O3 C16 O4 . . 126.0(2) ?
O3 C16 C15 . . 121.5(2) ?
O4 C16 C15 . . 112.5(2) ?
C16 C15 Cl1 . . 113.42(19) ?
C16 C15 H15A . . 108.9 ?
Cl1 C15 H15A . . 108.9 ?
C16 C15 H15B . . 108.9 ?
Cl1 C15 H15B . . 108.9 ?
H15A C15 H15B . . 107.7 ?
O1 C14 O2 . . 125.4(2) ?
O1 C14 C13 . . 116.1(2) ?
O2 C14 C13 . . 118.5(2) ?
C14 C13 Cl2 . . 115.3(2) ?
C14 C13 H13A . . 108.5 ?
Cl2 C13 H13A . . 108.5 ?
C14 C13 H13B . . 108.5 ?
Cl2 C13 H13B . . 108.5 ?
H13A C13 H13B . . 107.5 ?
C8 N5 C10 . . 119.4(2) ?
C8 N5 H5A . . 120.3 ?
C10 N5 H5A . . 120.3 ?
C12 N6 C10 . . 117.6(2) ?
N4 C10 N6 . . 118.5(2) ?
N4 C10 N5 . . 118.3(2) ?
N6 C10 N5 . . 123.2(2) ?
C8 C9 C12 . . 118.4(2) ?
C8 C9 H9A . . 120.8 ?
C12 C9 H9A . . 120.8 ?
N6 C12 C9 . . 121.8(2) ?
N6 C12 C11 . . 116.7(2) ?
C9 C12 C11 . . 121.5(2) ?
N5 C8 C9 . . 119.7(2) ?
N5 C8 C7 . . 117.8(2) ?
C9 C8 C7 . . 122.5(2) ?
C10 N4 H4A . . 120.0 ?
C10 N4 H4B . . 120.0 ?
H4A N4 H4B . . 120.0 ?
C8 C7 H7A . . 109.5 ?
C8 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C8 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C12 C11 H11A . . 109.5 ?
C12 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C12 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C2 N2 C4 . . 119.3(2) ?
C2 N2 H2A . . 120.4 ?
C4 N2 H2A . . 120.4 ?
C6 N3 C4 . . 117.5(2) ?
N3 C6 C3 . . 122.1(2) ?
N3 C6 C5 . . 116.2(2) ?
C3 C6 C5 . . 121.7(2) ?
C4 N1 H1A . . 120.0 ?
C4 N1 H1B . . 120.0 ?
H1A N1 H1B . . 120.0 ?
N1 C4 N3 . . 118.6(2) ?
N1 C4 N2 . . 118.3(2) ?
N3 C4 N2 . . 123.1(2) ?
N2 C2 C3 . . 119.7(2) ?
N2 C2 C1 . . 116.9(2) ?
C3 C2 C1 . . 123.4(2) ?
C2 C3 C6 . . 118.4(2) ?
C2 C3 H3B . . 120.8 ?
C6 C3 H3B . . 120.8 ?
C2 C1 H1C . . 109.5 ?
C2 C1 H1D . . 109.5 ?
H1C C1 H1D . . 109.5 ?
C2 C1 H1E . . 109.5 ?
H1C C1 H1E . . 109.5 ?
H1D C1 H1E . . 109.5 ?
C6 C5 H5B . . 109.5 ?
C6 C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C6 C5 H5D . . 109.5 ?
H5B C5 H5D . . 109.5 ?
H5C C5 H5D . . 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
Cl1 C15 . 1.766(3) ?
O4 C16 . 1.271(3) ?
C16 O3 . 1.219(3) ?
C16 C15 . 1.512(3) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
Cl2 C13 . 1.767(3) ?
O2 C14 . 1.273(3) ?
C14 O1 . 1.220(3) ?
C14 C13 . 1.507(4) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
N5 C8 . 1.337(3) ?
N5 C10 . 1.356(3) ?
N5 H5A . 0.8600 ?
N6 C12 . 1.331(3) ?
N6 C10 . 1.342(3) ?
C10 N4 . 1.322(3) ?
C9 C8 . 1.378(4) ?
C9 C12 . 1.389(3) ?
C9 H9A . 0.9300 ?
C12 C11 . 1.501(4) ?
C8 C7 . 1.495(3) ?
N4 H4A . 0.8600 ?
N4 H4B . 0.8600 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
N2 C2 . 1.347(3) ?
N2 C4 . 1.357(3) ?
N2 H2A . 0.8600 ?
N3 C6 . 1.331(3) ?
N3 C4 . 1.344(3) ?
C6 C3 . 1.389(4) ?
C6 C5 . 1.505(3) ?
N1 C4 . 1.326(3) ?
N1 H1A . 0.8600 ?
N1 H1B . 0.8600 ?
C2 C3 . 1.372(4) ?
C2 C1 . 1.493(4) ?
C3 H3B . 0.9300 ?
C1 H1C . 0.9600 ?
C1 H1D . 0.9600 ?
C1 H1E . 0.9600 ?
C5 H5B . 0.9600 ?
C5 H5C . 0.9600 ?
C5 H5D . 0.9600 ?
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
N1 H1A N3 2_465 0.86 2.14 2.999(3) 177
N1 H1B O3 2_665 0.86 1.98 2.830(3) 173
N2 H2A O4 2_665 0.86 1.74 2.593(3) 175
N4 H4A N6 2_556 0.86 2.19 3.046(3) 175
N4 H4B O1 1_455 0.86 2.00 2.851(3) 173
N5 H5A O2 1_455 0.86 1.75 2.606(3) 174
C1 H1C O4 2_665 0.96 2.56 3.355(4) 140
C7 H7A O2 1_455 0.96 2.57 3.355(4) 139
