#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/27/2012721.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_2012721 loop_ _publ_author_name 'Low, John N.' 'Quesada, Antonio' 'Marchal, Antonio' 'Melguizo, Manuel' 'Nogueras, Manuel' 'Glidewell, Christopher' _publ_section_title ; Hydrogen bonding in 2-amino-4,6-dimethoxypyrimidine, 2-benzylamino-4,6-bis(benzyloxy)pyrimidine and 2-amino-4,6-bis(N-pyrrolidino)pyrimidine: chains of fused rings and a centrosymmetric dimer ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o289 _journal_page_last o294 _journal_paper_doi 10.1107/S0108270102005632 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C6 H9 N3 O2' _chemical_formula_sum 'C6 H9 N3 O2' _chemical_formula_weight 155.16 _chemical_name_systematic ; 2-Amino-4,6-dimethoxypyrimidine ; _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 _cell_angle_alpha 90 _cell_angle_beta 106.585(3) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 12.3971(5) _cell_length_b 8.3608(5) _cell_length_c 14.5237(7) _cell_measurement_reflns_used 1642 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.42 _cell_measurement_theta_min 2.92 _cell_volume 1442.75(13) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD Server Software (Nonius, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.066 _diffrn_reflns_av_sigmaI/netI 0.065 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 5248 _diffrn_reflns_theta_full 27.42 _diffrn_reflns_theta_max 27.42 _diffrn_reflns_theta_min 2.92 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_correction_T_min 0.978 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO-SMN; Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 656 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.22 _refine_diff_density_min -0.37 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 102 _refine_ls_number_reflns 1642 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.011 _refine_ls_R_factor_all 0.087 _refine_ls_R_factor_gt 0.049 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0727P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.115 _refine_ls_wR_factor_ref 0.132 _reflns_number_gt 1090 _reflns_number_total 1642 _reflns_threshold_expression I>2\s(I) _cod_data_source_file sk1546.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' 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 The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2012721 _cod_database_fobs_code 2012721 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -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' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z+1/2' loop_ _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 _atom_site_type_symbol N1 0.14019(11) 0.48401(17) 0.48098(9) 0.0206(4) Uani d . 1 . . N N2 -0.01762(11) 0.37392(19) 0.37859(10) 0.0285(4) Uani d . 1 . . N N3 0.14982(11) 0.31903(17) 0.34783(9) 0.0205(4) Uani d . 1 . . N C2 0.09446(13) 0.3937(2) 0.40367(11) 0.0196(4) Uani d . 1 . . C O4 0.32450(9) 0.26690(14) 0.32742(8) 0.0244(3) Uani d . 1 . . O C4 0.26097(13) 0.3388(2) 0.37614(11) 0.0200(4) Uani d . 1 . . C C41 0.27005(15) 0.1574(2) 0.25231(12) 0.0266(4) Uani d . 1 . . C C5 0.31797(13) 0.4311(2) 0.45409(11) 0.0209(4) Uani d . 1 . . C O6 0.29165(9) 0.59379(15) 0.58250(8) 0.0253(3) Uani d . 1 . . O C6 0.25158(13) 0.5009(2) 0.50419(10) 0.0205(4) Uani d . 1 . . C C61 0.41058(14) 0.6223(2) 0.61287(13) 0.0307(5) Uani d . 1 . . C H2A -0.0576 0.4195 0.4126 0.034 Uiso calc R 1 . . H H2B -0.0511 0.3154 0.3282 0.034 Uiso calc R 1 . . H H41A 0.2195 0.0873 0.2749 0.040 Uiso calc R 1 . . H H41B 0.3270 0.0925 0.2347 0.040 Uiso calc R 1 . . H H41C 0.2265 0.2176 0.1961 0.040 Uiso calc R 1 . . H H5 0.3973 0.4451 0.4717 0.025 Uiso calc R 1 . . H H61A 0.4505 0.5200 0.6270 0.046 Uiso calc R 1 . . H H61B 0.4296 0.6889 0.6708 0.046 Uiso calc R 1 . . H H61C 0.4329 0.6774 0.5616 0.046 Uiso calc R 1 . . H 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 0.0176(8) 0.0247(8) 0.0192(7) 0.0026(6) 0.0048(6) -0.0002(6) N2 0.0161(8) 0.0425(10) 0.0265(8) 0.0012(7) 0.0051(6) -0.0114(7) N3 0.0207(8) 0.0233(8) 0.0185(7) 0.0011(6) 0.0071(6) 0.0008(6) C2 0.0196(9) 0.0207(10) 0.0186(8) 0.0022(7) 0.0055(7) 0.0038(7) O4 0.0221(7) 0.0297(7) 0.0224(6) 0.0025(5) 0.0081(5) -0.0049(5) C4 0.0208(9) 0.0219(10) 0.0186(8) 0.0050(7) 0.0077(7) 0.0055(7) C41 0.0307(10) 0.0255(10) 0.0258(9) 0.0012(8) 0.0114(8) -0.0046(8) C5 0.0153(8) 0.0248(10) 0.0222(8) 0.0006(7) 0.0047(7) 0.0003(7) O6 0.0191(7) 0.0349(8) 0.0213(6) -0.0007(5) 0.0046(5) -0.0076(5) C6 0.0210(9) 0.0223(10) 0.0173(8) 0.0016(7) 0.0042(7) 0.0006(7) C61 0.0174(9) 0.0414(12) 0.0303(10) -0.0002(8) 0.0018(8) -0.0118(8) 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 _geom_angle_publ_flag C6 N1 C2 115.64(13) no C2 N2 H2A 120.0 no C2 N2 H2B 120.0 no H2A N2 H2B 120.0 no C4 N3 C2 114.49(14) no N1 C2 N2 117.07(14) no N1 C2 N3 126.64(14) no N2 C2 N3 116.28(15) no C4 O4 C41 117.81(12) no N3 C4 O4 119.56(15) no N3 C4 C5 124.27(15) no O4 C4 C5 116.17(14) no O4 C41 H41A 109.5 no O4 C41 H41B 109.5 no H41A C41 H41B 109.5 no O4 C41 H41C 109.5 no H41A C41 H41C 109.5 no H41B C41 H41C 109.5 no C6 C5 C4 115.24(15) no C6 C5 H5 122.4 no C4 C5 H5 122.4 no C6 O6 C61 117.00(13) no N1 C6 O6 112.34(13) no N1 C6 C5 123.70(15) no O6 C6 C5 123.96(15) no O6 C61 H61A 109.5 no O6 C61 H61B 109.5 no H61A C61 H61B 109.5 no O6 C61 H61C 109.5 no H61A C61 H61C 109.5 no H61B C61 H61C 109.5 no 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 N1 C2 . 1.338(2) y C2 N3 . 1.355(2) y N3 C4 . 1.331(2) y C4 C5 . 1.386(2) y C5 C6 . 1.375(2) y C6 N1 . 1.332(2) y C2 N2 . 1.342(2) y C4 O4 . 1.342(2) y O4 C41 . 1.437(2) y C6 O6 . 1.3492(19) y O6 C61 . 1.433(2) y N2 H2A . 0.8800 no N2 H2B . 0.8800 no C41 H41A . 0.9800 no C41 H41B . 0.9800 no C41 H41C . 0.9800 no C5 H5 . 0.9500 no C61 H61A . 0.9800 no C61 H61B . 0.9800 no C61 H61C . 0.9800 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 N2 H2A N1 3_566 0.88 2.23 3.106(2) 171 y N2 H2B N3 2_555 0.88 2.50 3.261(2) 145 y 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 179.80(15) no C6 N1 C2 N3 0.1(2) no C4 N3 C2 N1 1.1(2) no C4 N3 C2 N2 -178.68(14) no C2 N3 C4 O4 178.40(14) no C2 N3 C4 C5 -1.9(2) no C41 O4 C4 N3 -6.5(2) y C41 O4 C4 C5 173.81(15) no N3 C4 C5 C6 1.6(2) no O4 C4 C5 C6 -178.70(14) no C2 N1 C6 O6 179.78(13) no C2 N1 C6 C5 -0.4(2) no C61 O6 C6 N1 -178.95(15) no C61 O6 C6 C5 1.3(2) y C4 C5 C6 N1 -0.3(3) no C4 C5 C6 O6 179.44(15) no