#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/27/2012723.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_2012723 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 'C12 H19 N5' _chemical_formula_sum 'C12 H19 N5' _chemical_formula_weight 233.32 _chemical_name_systematic ; 2-amino-4,6-bis(N-pyrrolidino)pyrimidine ; _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 93.090(2) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 12.5654(8) _cell_length_b 13.2735(8) _cell_length_c 14.2279(9) _cell_measurement_reflns_used 2485 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.61 _cell_measurement_theta_min 2.23 _cell_volume 2369.6(3) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD Server Software (Nonius, 1997)' _computing_data_reduction DENZO-SMN _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 0.999 _diffrn_measured_fraction_theta_max 0.961 _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 0.022 _diffrn_reflns_av_sigmaI/netI 0.020 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 7257 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 2.23 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_correction_T_min 0.975 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO-SMN; Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1008 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.24 _refine_diff_density_min -0.31 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 2485 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.076 _refine_ls_R_factor_all 0.048 _refine_ls_R_factor_gt 0.041 _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^)+(0.0753P)^2^+0.6604P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.113 _refine_ls_wR_factor_ref 0.117 _reflns_number_gt 2109 _reflns_number_total 2485 _reflns_threshold_expression I>2\s(I) _cod_data_source_file sk1546.cif _cod_data_source_block III _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 2012723 _cod_database_fobs_code 2012723 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 0.14234(7) 0.42768(7) 0.04220(6) 0.0167(2) Uani d . 1 . . N C2 0.08934(9) 0.41017(8) 0.12032(8) 0.0169(3) Uani d . 1 . . C N2 -0.01134(8) 0.44606(8) 0.12240(7) 0.0226(3) Uani d . 1 . . N N3 0.12512(7) 0.36133(7) 0.19908(6) 0.0177(2) Uani d . 1 . . N C4 0.22452(9) 0.32333(8) 0.19736(8) 0.0168(3) Uani d . 1 . . C N4 0.25920(7) 0.27045(8) 0.27487(7) 0.0210(3) Uani d . 1 . . N C41 0.19010(9) 0.24157(9) 0.34986(8) 0.0200(3) Uani d . 1 . . C C42 0.25113(10) 0.15405(9) 0.39630(9) 0.0247(3) Uani d . 1 . . C C43 0.36722(10) 0.18595(10) 0.38874(9) 0.0248(3) Uani d . 1 . . C C44 0.36740(9) 0.23140(9) 0.28994(8) 0.0203(3) Uani d . 1 . . C C5 0.28893(9) 0.33753(8) 0.12149(8) 0.0181(3) Uani d . 1 . . C C6 0.24377(9) 0.39189(8) 0.04469(8) 0.0163(3) Uani d . 1 . . C N6 0.30145(7) 0.41109(7) -0.03098(7) 0.0190(2) Uani d . 1 . . N C61 0.41069(9) 0.37530(9) -0.03849(8) 0.0193(3) Uani d . 1 . . C C62 0.44028(10) 0.41074(9) -0.13600(8) 0.0228(3) Uani d . 1 . . C C63 0.36687(9) 0.50100(9) -0.15631(8) 0.0216(3) Uani d . 1 . . C C64 0.26383(9) 0.47094(9) -0.11223(8) 0.0188(3) Uani d . 1 . . C H2A -0.0398 0.4794 0.0738 0.027 Uiso calc R 1 . . H H2B -0.0484 0.4360 0.1723 0.027 Uiso calc R 1 . . H H41A 0.1190 0.2200 0.3240 0.024 Uiso calc R 1 . . H H41B 0.1814 0.2976 0.3947 0.024 Uiso calc R 1 . . H H42A 0.2360 0.0901 0.3623 0.030 Uiso calc R 1 . . H H42B 0.2334 0.1461 0.4628 0.030 Uiso calc R 1 . . H H43A 0.4158 0.1273 0.3950 0.030 Uiso calc R 1 . . H H43B 0.3885 0.2365 0.4374 0.030 Uiso calc R 1 . . H H44A 0.4207 0.2861 0.2871 0.024 Uiso calc R 1 . . H H44B 0.3827 0.1794 0.2426 0.024 Uiso calc R 1 . . H H5 0.3595 0.3118 0.1218 0.022 Uiso calc R 1 . . H H61A 0.4142 0.3010 -0.0336 0.023 Uiso calc R 1 . . H H61B 0.4589 0.4051 0.0114 0.023 Uiso calc R 1 . . H H62A 0.4272 0.3570 -0.1835 0.027 Uiso calc R 1 . . H H62B 0.5161 0.4311 -0.1355 0.027 Uiso calc R 1 . . H H63A 0.3970 0.5631 -0.1270 0.026 Uiso calc R 1 . . H H63B 0.3550 0.5120 -0.2249 0.026 Uiso calc R 1 . . H H64A 0.2238 0.5309 -0.0926 0.023 Uiso calc R 1 . . H H64B 0.2178 0.4305 -0.1565 0.023 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 0.0156(5) 0.0198(5) 0.0148(5) 0.0000(4) 0.0009(4) 0.0007(4) C2 0.0159(5) 0.0186(5) 0.0161(6) -0.0027(4) 0.0003(4) -0.0009(4) N2 0.0161(5) 0.0349(6) 0.0172(5) 0.0040(4) 0.0034(4) 0.0079(4) N3 0.0152(5) 0.0231(5) 0.0147(5) -0.0005(4) 0.0009(4) 0.0016(4) C4 0.0182(6) 0.0173(5) 0.0148(5) -0.0023(4) -0.0007(4) -0.0001(4) N4 0.0162(5) 0.0288(5) 0.0183(5) 0.0021(4) 0.0023(4) 0.0070(4) C41 0.0205(6) 0.0244(6) 0.0149(6) -0.0020(5) 0.0005(4) 0.0031(4) C42 0.0292(7) 0.0246(6) 0.0203(6) -0.0008(5) -0.0002(5) 0.0053(5) C43 0.0252(7) 0.0264(6) 0.0225(6) 0.0037(5) -0.0027(5) 0.0047(5) C44 0.0176(6) 0.0234(6) 0.0197(6) 0.0029(5) -0.0001(4) 0.0005(5) C5 0.0154(5) 0.0210(6) 0.0179(6) 0.0024(4) 0.0017(4) 0.0011(4) C6 0.0175(6) 0.0162(5) 0.0151(6) -0.0011(4) 0.0016(4) -0.0020(4) N6 0.0173(5) 0.0249(5) 0.0152(5) 0.0049(4) 0.0038(4) 0.0037(4) C61 0.0163(6) 0.0237(6) 0.0181(6) 0.0033(4) 0.0040(4) 0.0004(4) C62 0.0215(6) 0.0283(6) 0.0191(6) 0.0021(5) 0.0068(5) 0.0009(5) C63 0.0203(6) 0.0282(6) 0.0166(6) 0.0001(5) 0.0028(4) 0.0028(5) C64 0.0190(6) 0.0229(6) 0.0144(6) 0.0002(4) -0.0004(4) 0.0016(4) 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 _geom_angle_publ_flag C2 N1 C6 115.03(10) no N1 C2 N3 127.63(10) no N1 C2 N2 117.50(10) no N3 C2 N2 114.87(10) no C2 N2 H2A 120.0 no C2 N2 H2B 120.0 no H2A N2 H2B 120.0 no C4 N3 C2 115.58(10) no N3 C4 N4 115.80(10) no N3 C4 C5 122.65(10) no N4 C4 C5 121.55(10) no C4 N4 C41 123.39(9) y C4 N4 C44 123.91(10) y C41 N4 C44 112.62(9) y N4 C41 C42 102.22(9) no N4 C41 H41A 111.3 no C42 C41 H41A 111.3 no N4 C41 H41B 111.3 no C42 C41 H41B 111.3 no H41A C41 H41B 109.2 no C41 C42 C43 102.61(9) no C41 C42 H42A 111.2 no C43 C42 H42A 111.2 no C41 C42 H42B 111.2 no C43 C42 H42B 111.2 no H42A C42 H42B 109.2 no C42 C43 C44 102.87(9) no C42 C43 H43A 111.2 no C44 C43 H43A 111.2 no C42 C43 H43B 111.2 no C44 C43 H43B 111.2 no H43A C43 H43B 109.1 no N4 C44 C43 103.14(9) no N4 C44 H44A 111.1 no C43 C44 H44A 111.1 no N4 C44 H44B 111.1 no C43 C44 H44B 111.1 no H44A C44 H44B 109.1 no C4 C5 C6 116.39(10) no C4 C5 H5 121.8 no C6 C5 H5 121.8 no N6 C6 N1 117.06(10) no N6 C6 C5 120.30(10) no N1 C6 C5 122.64(10) no C6 N6 C61 122.82(9) y C6 N6 C64 124.58(9) y C61 N6 C64 112.58(9) y N6 C61 C62 103.98(9) no N6 C61 H61A 111.0 no C62 C61 H61A 111.0 no N6 C61 H61B 111.0 no C62 C61 H61B 111.0 no H61A C61 H61B 109.0 no C61 C62 C63 103.80(9) no C61 C62 H62A 111.0 no C63 C62 H62A 111.0 no C61 C62 H62B 111.0 no C63 C62 H62B 111.0 no H62A C62 H62B 109.0 no C64 C63 C62 103.56(9) no C64 C63 H63A 111.0 no C62 C63 H63A 111.0 no C64 C63 H63B 111.0 no C62 C63 H63B 111.0 no H63A C63 H63B 109.0 no N6 C64 C63 102.86(9) no N6 C64 H64A 111.2 no C63 C64 H64A 111.2 no N6 C64 H64B 111.2 no C63 C64 H64B 111.2 no H64A C64 H64B 109.1 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 . 1.3464(15) y C2 N3 . 1.3506(14) y N3 C4 . 1.3484(15) y C4 C5 . 1.3965(16) y C5 C6 . 1.4035(15) y C6 N1 . 1.3588(14) y C2 N2 . 1.3537(15) y N2 H2A . 0.8800 no N2 H2B . 0.8800 no C4 N4 . 1.3590(14) y N4 C44 . 1.4601(14) no N4 C41 . 1.4625(15) no C41 C42 . 1.5230(16) no C41 H41A . 0.9900 no C41 H41B . 0.9900 no C42 C43 . 1.5283(18) no C42 H42A . 0.9900 no C42 H42B . 0.9900 no C43 C44 . 1.5298(16) no C43 H43A . 0.9900 no C43 H43B . 0.9900 no C44 H44A . 0.9900 no C44 H44B . 0.9900 no C5 H5 . 0.9500 no C6 N6 . 1.3540(15) y N6 C64 . 1.4602(14) no N6 C61 . 1.4619(14) no C61 C62 . 1.5296(16) no C61 H61A . 0.9900 no C61 H61B . 0.9900 no C62 C63 . 1.5300(16) no C62 H62A . 0.9900 no C62 H62B . 0.9900 no C63 C64 . 1.5219(16) no C63 H63A . 0.9900 no C63 H63B . 0.9900 no C64 H64A . 0.9900 no C64 H64B . 0.9900 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_565 0.88 2.38 3.2538(14) 170 y N2 H2B N3 2_555 0.88 2.33 3.1862(13) 163 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 N3 -0.43(17) no C6 N1 C2 N2 178.66(9) no N1 C2 N3 C4 -2.19(17) no N2 C2 N3 C4 178.70(9) no C2 N3 C4 N4 -177.32(9) no C2 N3 C4 C5 3.17(16) no N3 C4 N4 C44 -174.24(10) no N3 C4 N4 C41 9.39(16) y C5 C4 N4 C44 5.27(17) y C5 C4 N4 C41 -171.10(11) no C4 N4 C41 C42 158.93(11) no N4 C41 C42 C43 35.48(12) y C41 C42 C43 C44 -40.59(12) y C42 C43 C44 N4 29.44(12) y C43 C44 N4 C41 -7.37(13) y C44 N4 C41 C42 -17.80(13) y C4 N4 C44 C43 175.92(11) no N3 C4 C5 C6 -1.63(16) no N4 C4 C5 C6 178.90(10) no C2 N1 C6 N6 -177.58(9) no C2 N1 C6 C5 2.18(16) no C4 C5 C6 N6 178.52(10) no C4 C5 C6 N1 -1.23(17) no C5 C6 N6 C64 -176.89(10) no N1 C6 N6 C61 -178.70(9) no C5 C6 N6 C61 1.53(17) y N1 C6 N6 C64 2.88(16) y C6 N6 C61 C62 177.59(10) no N6 C64 C63 C62 33.10(11) y C64 C63 C62 C61 -35.97(12) y C63 C62 C61 N6 24.55(12) y C62 C61 N6 C64 -3.82(13) y C61 N6 C64 C63 -18.54(12) y C6 N6 C64 C63 160.02(11) no