#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/72/2237220.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_2237220
loop_
_publ_author_name
'Fu, Wei-Wei'
'Liu, Yang'
'Huang, Geng'
'Zhu, Xiao-Ming'
_publ_section_title
;
 4,6-Dimethylpyrimidin-2-amine
;
_journal_coeditor_code           RZ5030
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o32
_journal_paper_doi               10.1107/S1600536812049458
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C6 H9 N3'
_chemical_formula_moiety         'C6 H9 N3'
_chemical_formula_sum            'C6 H9 N3'
_chemical_formula_weight         123.16
_chemical_name_systematic
;
4,6-Dimethylpyrimidin-2-amine
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 91.112(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            24
_cell_length_a                   11.519(7)
_cell_length_b                   11.021(6)
_cell_length_c                   32.386(18)
_cell_measurement_reflns_used    1760
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.00
_cell_measurement_theta_min      2.56
_cell_volume                     4111(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            11005
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_correction_T_min  0.9800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         1.081
_refine_diff_density_min         -0.158
_refine_ls_extinction_coef       0.0011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4020
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0619
_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)+(0.0567P)²+5.4094P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1754
_reflns_number_gt                2252
_reflns_number_total             4020
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            rz5030.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2237220
_cod_database_fobs_code          2237220
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
N N1 0.47955(19) 0.1483(2) 0.53927(8) 0.0677(7) Uani d . 1 1
H H1A 0.4423 0.0961 0.5244 0.081 Uiso calc R 1 1
H H1B 0.4422 0.2003 0.5537 0.081 Uiso calc R 1 1
N N2 0.64988(18) 0.0645(2) 0.51683(7) 0.0514(6) Uani d . 1 1
N N3 0.65035(18) 0.2326(2) 0.56391(6) 0.0497(6) Uani d . 1 1
N N4 -0.0008(2) 0.2232(2) 0.69589(8) 0.0702(8) Uani d . 1 1
H H4A -0.0320 0.1741 0.6783 0.084 Uiso calc R 1 1
H H4B -0.0438 0.2682 0.7110 0.084 Uiso calc R 1 1
N N5 0.17824(19) 0.1573(2) 0.67544(7) 0.0513(6) Uani d . 1 1
N N6 0.15897(19) 0.3101(2) 0.72784(7) 0.0528(6) Uani d . 1 1
N N7 1.03321(19) 0.9393(2) 0.61966(8) 0.0705(8) Uani d . 1 1
H H7A 1.0747 0.9889 0.6342 0.085 Uiso calc R 1 1
H H7B 1.0662 0.8868 0.6042 0.085 Uiso calc R 1 1
N N8 0.85527(19) 0.8637(2) 0.59788(7) 0.0522(6) Uani d . 1 1
N N9 0.87060(18) 1.0286(2) 0.64615(7) 0.0507(6) Uani d . 1 1
C C1 0.5969(2) 0.1484(2) 0.54006(8) 0.0481(6) Uani d . 1 1
C C2 0.7663(2) 0.0667(2) 0.51776(8) 0.0533(7) Uani d . 1 1
C C3 0.8282(2) 0.1495(3) 0.54127(9) 0.0572(7) Uani d . 1 1
H H3A 0.9090 0.1498 0.5416 0.069 Uiso calc R 1 1
C C4 0.7666(2) 0.2320(2) 0.56421(8) 0.0515(7) Uani d . 1 1
C C5 0.8265(3) -0.0260(3) 0.49198(11) 0.0766(10) Uani d . 1 1
H H5A 0.7697 -0.0748 0.4776 0.115 Uiso calc R 1 1
H H5B 0.8739 -0.0769 0.5095 0.115 Uiso calc R 1 1
H H5C 0.8745 0.0142 0.4723 0.115 Uiso calc R 1 1
C C6 0.8267(3) 0.3251(3) 0.59082(11) 0.0743(9) Uani d . 1 1
H H6A 0.7698 0.3739 0.6043 0.111 Uiso calc R 1 1
H H6B 0.8741 0.3759 0.5740 0.111 Uiso calc R 1 1
H H6C 0.8747 0.2850 0.6112 0.111 Uiso calc R 1 1
C C7 0.1161(2) 0.2298(2) 0.69984(8) 0.0487(6) Uani d . 1 1
C C8 0.2939(2) 0.1687(2) 0.67901(9) 0.0547(7) Uani d . 1 1
C C9 0.3449(2) 0.2505(3) 0.70623(9) 0.0597(8) Uani d . 1 1
H H9A 0.4252 0.2582 0.7081 0.072 Uiso calc R 1 1
C C10 0.2743(2) 0.3200(2) 0.73041(8) 0.0520(7) Uani d . 1 1
C C11 0.3651(3) 0.0882(3) 0.65230(12) 0.0846(11) Uani d . 1 1
H H11A 0.3146 0.0383 0.6356 0.127 Uiso calc R 1 1
H H11B 0.4139 0.0375 0.6694 0.127 Uiso calc R 1 1
H H11C 0.4125 0.1370 0.6348 0.127 Uiso calc R 1 1
C C12 0.3216(3) 0.4120(3) 0.76051(10) 0.0744(9) Uani d . 1 1
H H12A 0.2585 0.4510 0.7742 0.112 Uiso calc R 1 1
H H12B 0.3659 0.4716 0.7460 0.112 Uiso calc R 1 1
H H12C 0.3707 0.3722 0.7806 0.112 Uiso calc R 1 1
C C13 0.9157(2) 0.9440(2) 0.62120(8) 0.0490(6) Uani d . 1 1
C C14 0.7390(2) 0.8696(3) 0.60022(9) 0.0546(7) Uani d . 1 1
C C15 0.6851(2) 0.9530(3) 0.62522(9) 0.0582(7) Uani d . 1 1
H H15A 0.6046 0.9561 0.6267 0.070 Uiso calc R 1 1
C C16 0.7545(2) 1.0319(2) 0.64800(8) 0.0515(7) Uani d . 1 1
C C17 0.6703(3) 0.7818(3) 0.57420(11) 0.0779(10) Uani d . 1 1
H H17A 0.7223 0.7314 0.5590 0.117 Uiso calc R 1 1
H H17B 0.6208 0.8257 0.5553 0.117 Uiso calc R 1 1
H H17C 0.6237 0.7319 0.5917 0.117 Uiso calc R 1 1
C C18 0.7026(3) 1.1255(3) 0.67570(10) 0.0759(10) Uani d . 1 1
H H18A 0.7635 1.1713 0.6890 0.114 Uiso calc R 1 1
H H18B 0.6569 1.0860 0.6962 0.114 Uiso calc R 1 1
H H18C 0.6540 1.1790 0.6596 0.114 Uiso calc R 1 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 H1A 120.0
C1 N1 H1B 120.0
H1A N1 H1B 120.0
C2 N2 C1 116.1(2)
C4 N3 C1 116.5(2)
C7 N4 H4A 120.0
C7 N4 H4B 120.0
H4A N4 H4B 120.0
C8 N5 C7 115.7(2)
C10 N6 C7 116.5(2)
C13 N7 H7A 120.0
C13 N7 H7B 120.0
H7A N7 H7B 120.0
C14 N8 C13 116.1(2)
C16 N9 C13 116.3(2)
N2 C1 N3 125.8(2)
N2 C1 N1 116.9(2)
N3 C1 N1 117.2(2)
N2 C2 C3 122.1(2)
N2 C2 C5 116.7(3)
C3 C2 C5 121.2(3)
C2 C3 C4 117.8(3)
C2 C3 H3A 121.1
C4 C3 H3A 121.1
N3 C4 C3 121.6(2)
N3 C4 C6 116.8(2)
C3 C4 C6 121.5(3)
C2 C5 H5A 109.5
C2 C5 H5B 109.5
H5A C5 H5B 109.5
C2 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C4 C6 H6A 109.5
C4 C6 H6B 109.5
H6A C6 H6B 109.5
C4 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N5 C7 N4 117.0(2)
N5 C7 N6 126.3(2)
N4 C7 N6 116.6(2)
N5 C8 C9 121.7(3)
N5 C8 C11 116.7(3)
C9 C8 C11 121.6(3)
C10 C9 C8 118.5(3)
C10 C9 H9A 120.7
C8 C9 H9A 120.7
N6 C10 C9 121.3(3)
N6 C10 C12 116.4(3)
C9 C10 C12 122.4(3)
C8 C11 H11A 109.5
C8 C11 H11B 109.5
H11A C11 H11B 109.5
C8 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C10 C12 H12A 109.5
C10 C12 H12B 109.5
H12A C12 H12B 109.5
C10 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
N9 C13 N8 126.2(2)
N9 C13 N7 116.5(2)
N8 C13 N7 117.3(2)
N8 C14 C15 121.7(3)
N8 C14 C17 116.9(3)
C15 C14 C17 121.4(3)
C14 C15 C16 118.0(3)
C14 C15 H15A 121.0
C16 C15 H15A 121.0
N9 C16 C15 121.7(2)
N9 C16 C18 117.1(2)
C15 C16 C18 121.2(2)
C14 C17 H17A 109.5
C14 C17 H17B 109.5
H17A C17 H17B 109.5
C14 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C16 C18 H18A 109.5
C16 C18 H18B 109.5
H18A C18 H18B 109.5
C16 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.351(3)
N1 H1A 0.8600
N1 H1B 0.8600
N2 C2 1.341(3)
N2 C1 1.346(3)
N3 C4 1.339(3)
N3 C1 1.349(3)
N4 C7 1.351(3)
N4 H4A 0.8600
N4 H4B 0.8600
N5 C8 1.341(3)
N5 C7 1.341(3)
N6 C10 1.334(3)
N6 C7 1.354(3)
N7 C13 1.357(3)
N7 H7A 0.8600
N7 H7B 0.8600
N8 C14 1.345(3)
N8 C13 1.348(3)
N9 C16 1.340(3)
N9 C13 1.344(3)
C2 C3 1.379(4)
C2 C5 1.499(4)
C3 C4 1.380(4)
C3 H3A 0.9300
C4 C6 1.500(4)
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C8 C9 1.383(4)
C8 C11 1.496(4)
C9 C10 1.373(4)
C9 H9A 0.9300
C10 C12 1.502(4)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C14 C15 1.380(4)
C14 C17 1.499(4)
C15 C16 1.384(4)
C15 H15A 0.9300
C16 C18 1.499(4)
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 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 N2 5_656 0.86 2.45 3.304(4) 175.0
N1 H1B N8 3_445 0.86 2.52 3.376(4) 173.3
N4 H4A N9 1_445 0.86 2.21 3.050(3) 166.6
N4 H4B N6 2_556 0.86 2.45 3.243(4) 153.5
N7 H7A N5 1_665 0.86 2.57 3.421(4) 172.6
N7 H7B N3 3 0.86 2.36 3.219(3) 176.3
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
C2 N2 C1 N3 -0.3(4)
C2 N2 C1 N1 179.5(3)
C4 N3 C1 N2 0.2(4)
C4 N3 C1 N1 -179.7(3)
C1 N2 C2 C3 0.3(4)
C1 N2 C2 C5 -179.9(3)
N2 C2 C3 C4 -0.2(4)
C5 C2 C3 C4 -179.9(3)
C1 N3 C4 C3 0.0(4)
C1 N3 C4 C6 -179.7(3)
C2 C3 C4 N3 0.0(4)
C2 C3 C4 C6 179.7(3)
C8 N5 C7 N4 177.8(3)
C8 N5 C7 N6 -1.5(4)
C10 N6 C7 N5 2.0(4)
C10 N6 C7 N4 -177.3(2)
C7 N5 C8 C9 0.0(4)
C7 N5 C8 C11 179.6(3)
N5 C8 C9 C10 0.8(4)
C11 C8 C9 C10 -178.7(3)
C7 N6 C10 C9 -1.0(4)
C7 N6 C10 C12 178.1(2)
C8 C9 C10 N6 -0.3(4)
C8 C9 C10 C12 -179.3(3)
C16 N9 C13 N8 0.6(4)
C16 N9 C13 N7 -179.2(3)
C14 N8 C13 N9 -0.2(4)
C14 N8 C13 N7 179.5(3)
C13 N8 C14 C15 -0.2(4)
C13 N8 C14 C17 179.5(3)
N8 C14 C15 C16 0.3(4)
C17 C14 C15 C16 -179.4(3)
C13 N9 C16 C15 -0.4(4)
C13 N9 C16 C18 179.9(3)
C14 C15 C16 N9 0.1(4)
C14 C15 C16 C18 179.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12480
2 PubChem 139085085
