#------------------------------------------------------------------------------ #$Date: 2015-01-23 14:30:19 +0200 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/27/2012722.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_2012722 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 'C25 H23 N3 O2' _chemical_formula_sum 'C25 H23 N3 O2' _chemical_formula_weight 397.46 _chemical_name_systematic ; 2-Benzylamino-4,6-bis(benzyloxy)pyrimidine ; _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 68.549(2) _cell_angle_beta 85.978(2) _cell_angle_gamma 82.737(2) _cell_formula_units_Z 2 _cell_length_a 5.8083(6) _cell_length_b 12.3104(13) _cell_length_c 15.7260(16) _cell_measurement_reflns_used 4785 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 29.04 _cell_measurement_theta_min 1.79 _cell_volume 1037.81(19) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction 'SHELXTL (Bruker, 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 0.983 _diffrn_measured_fraction_theta_max 0.865 _diffrn_measurement_device_type 'Bruker SMART 1000' _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 0.010 _diffrn_reflns_av_sigmaI/netI 0.026 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 6639 _diffrn_reflns_theta_full 26.50 _diffrn_reflns_theta_max 29.04 _diffrn_reflns_theta_min 1.79 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_correction_T_min 0.989 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 420 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.25 _refine_diff_density_min -0.22 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 271 _refine_ls_number_reflns 4785 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.067 _refine_ls_R_factor_all 0.056 _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^)+(0.0612P)^2^+0.0805P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.105 _refine_ls_wR_factor_ref 0.111 _reflns_number_gt 3697 _reflns_number_total 4785 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1546.cif _[local]_cod_data_source_block II _[local]_cod_cif_authors_sg_H-M P-1 _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_database_code 2012722 _cod_database_fobs_code 2012722 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 1.06020(18) 0.15079(9) 0.43312(7) 0.0245(2) Uani d . 1 . . N C2 0.9040(2) 0.14975(10) 0.37413(8) 0.0234(2) Uani d . 1 . . C N2 0.81278(19) 0.04843(9) 0.39253(7) 0.0279(2) Uani d . 1 . . N C27 0.6332(2) 0.03365(11) 0.33940(8) 0.0261(3) Uani d . 1 . . C C21 0.7221(2) -0.00571(10) 0.26110(8) 0.0231(3) Uani d . 1 . . C C22 0.5881(2) -0.07097(11) 0.23235(8) 0.0275(3) Uani d . 1 . . C C23 0.6605(2) -0.10549(11) 0.15896(9) 0.0328(3) Uani d . 1 . . C C24 0.8691(2) -0.07512(12) 0.11369(9) 0.0334(3) Uani d . 1 . . C C25 1.0057(2) -0.01108(12) 0.14225(9) 0.0317(3) Uani d . 1 . . C C26 0.9327(2) 0.02341(11) 0.21554(8) 0.0272(3) Uani d . 1 . . C N3 0.82976(18) 0.24202(8) 0.29875(6) 0.0249(2) Uani d . 1 . . N C4 0.9258(2) 0.33947(10) 0.28374(8) 0.0238(3) Uani d . 1 . . C O4 0.85807(15) 0.43613(7) 0.21106(6) 0.0280(2) Uani d . 1 . . O C47 0.6792(2) 0.42567(11) 0.15532(9) 0.0321(3) Uani d . 1 . . C C41 0.6113(2) 0.54692(11) 0.08775(8) 0.0278(3) Uani d . 1 . . C C42 0.7715(3) 0.60873(13) 0.02532(11) 0.0409(3) Uani d . 1 . . C C43 0.7082(3) 0.72002(13) -0.03715(11) 0.0454(4) Uani d . 1 . . C C44 0.4837(3) 0.77170(12) -0.03714(10) 0.0392(3) Uani d . 1 . . C C45 0.3238(3) 0.71142(13) 0.02456(10) 0.0396(3) Uani d . 1 . . C C46 0.3856(2) 0.59913(12) 0.08676(9) 0.0334(3) Uani d . 1 . . C C5 1.0904(2) 0.35194(10) 0.33882(8) 0.0257(3) Uani d . 1 . . C C6 1.1484(2) 0.25220(10) 0.41456(8) 0.0237(3) Uani d . 1 . . C O6 1.29228(15) 0.24744(7) 0.48017(6) 0.0284(2) Uani d . 1 . . O C67 1.3823(3) 0.35596(11) 0.47016(9) 0.0338(3) Uani d . 1 . . C C61 1.5029(2) 0.34046(10) 0.55579(8) 0.0264(3) Uani d . 1 . . C C62 1.3964(2) 0.38608(11) 0.61912(9) 0.0280(3) Uani d . 1 . . C C63 1.5120(3) 0.37561(11) 0.69647(9) 0.0332(3) Uani d . 1 . . C C64 1.7358(2) 0.32039(11) 0.71061(9) 0.0347(3) Uani d . 1 . . C C65 1.8430(2) 0.27374(12) 0.64840(10) 0.0355(3) Uani d . 1 . . C C66 1.7265(2) 0.28324(11) 0.57154(9) 0.0320(3) Uani d . 1 . . C H2 0.8652 -0.0127 0.4397 0.033 Uiso calc R 1 . . H H27A 0.5340 0.1092 0.3143 0.031 Uiso calc R 1 . . H H27B 0.5343 -0.0248 0.3807 0.031 Uiso calc R 1 . . H H22 0.4449 -0.0923 0.2633 0.033 Uiso calc R 1 . . H H23 0.5667 -0.1499 0.1399 0.039 Uiso calc R 1 . . H H24 0.9185 -0.0981 0.0633 0.040 Uiso calc R 1 . . H H25 1.1497 0.0093 0.1116 0.038 Uiso calc R 1 . . H H26 1.0274 0.0673 0.2347 0.033 Uiso calc R 1 . . H H47A 0.5433 0.3942 0.1940 0.039 Uiso calc R 1 . . H H47B 0.7393 0.3720 0.1230 0.039 Uiso calc R 1 . . H H42 0.9273 0.5743 0.0253 0.049 Uiso calc R 1 . . H H43 0.8199 0.7608 -0.0801 0.054 Uiso calc R 1 . . H H44 0.4401 0.8484 -0.0795 0.047 Uiso calc R 1 . . H H45 0.1687 0.7468 0.0249 0.048 Uiso calc R 1 . . H H46 0.2725 0.5581 0.1288 0.040 Uiso calc R 1 . . H H5 1.1575 0.4230 0.3256 0.031 Uiso calc R 1 . . H H67A 1.2535 0.4200 0.4589 0.041 Uiso calc R 1 . . H H67B 1.4928 0.3774 0.4173 0.041 Uiso calc R 1 . . H H62 1.2431 0.4248 0.6094 0.034 Uiso calc R 1 . . H H63 1.4371 0.4065 0.7398 0.040 Uiso calc R 1 . . H H64 1.8158 0.3145 0.7630 0.042 Uiso calc R 1 . . H H65 1.9964 0.2352 0.6583 0.043 Uiso calc R 1 . . H H66 1.8002 0.2503 0.5293 0.038 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 0.0330(5) 0.0203(5) 0.0203(5) -0.0065(4) -0.0032(4) -0.0059(4) C2 0.0304(6) 0.0205(6) 0.0201(5) -0.0048(5) -0.0013(5) -0.0075(5) N2 0.0402(6) 0.0199(5) 0.0222(5) -0.0094(4) -0.0091(4) -0.0023(4) C27 0.0303(6) 0.0233(6) 0.0243(6) -0.0088(5) -0.0026(5) -0.0057(5) C21 0.0271(6) 0.0169(5) 0.0217(6) -0.0023(5) -0.0078(5) -0.0015(4) C22 0.0299(6) 0.0247(6) 0.0260(6) -0.0081(5) -0.0049(5) -0.0046(5) C23 0.0461(8) 0.0262(7) 0.0279(6) -0.0101(6) -0.0085(6) -0.0085(5) C24 0.0446(8) 0.0274(7) 0.0271(6) 0.0002(6) -0.0030(6) -0.0093(5) C25 0.0284(6) 0.0323(7) 0.0296(7) -0.0019(5) -0.0005(5) -0.0061(5) C26 0.0274(6) 0.0247(6) 0.0275(6) -0.0041(5) -0.0068(5) -0.0056(5) N3 0.0324(5) 0.0193(5) 0.0218(5) -0.0053(4) -0.0045(4) -0.0046(4) C4 0.0309(6) 0.0191(6) 0.0203(6) -0.0023(5) -0.0010(5) -0.0059(5) O4 0.0378(5) 0.0181(4) 0.0256(4) -0.0051(4) -0.0107(4) -0.0022(3) C47 0.0411(7) 0.0227(6) 0.0307(7) -0.0063(5) -0.0142(6) -0.0042(5) C41 0.0355(7) 0.0226(6) 0.0256(6) -0.0041(5) -0.0099(5) -0.0072(5) C42 0.0337(7) 0.0290(7) 0.0494(9) -0.0022(6) -0.0051(6) -0.0015(6) C43 0.0456(9) 0.0336(8) 0.0448(9) -0.0112(7) -0.0049(7) 0.0031(7) C44 0.0516(9) 0.0231(7) 0.0382(8) -0.0018(6) -0.0217(7) -0.0028(6) C45 0.0378(7) 0.0342(8) 0.0469(8) 0.0060(6) -0.0136(7) -0.0156(7) C46 0.0377(7) 0.0339(7) 0.0286(7) -0.0040(6) -0.0035(5) -0.0109(6) C5 0.0347(7) 0.0187(6) 0.0234(6) -0.0082(5) -0.0031(5) -0.0051(5) C6 0.0297(6) 0.0229(6) 0.0200(6) -0.0063(5) -0.0017(5) -0.0082(5) O6 0.0403(5) 0.0219(4) 0.0230(4) -0.0114(4) -0.0085(4) -0.0041(3) C67 0.0506(8) 0.0252(6) 0.0265(6) -0.0170(6) -0.0090(6) -0.0046(5) C61 0.0326(6) 0.0216(6) 0.0247(6) -0.0114(5) -0.0025(5) -0.0048(5) C62 0.0293(6) 0.0215(6) 0.0316(7) -0.0060(5) -0.0022(5) -0.0064(5) C63 0.0482(8) 0.0250(6) 0.0285(7) -0.0104(6) 0.0007(6) -0.0104(5) C64 0.0466(8) 0.0259(7) 0.0298(7) -0.0120(6) -0.0142(6) -0.0030(5) C65 0.0272(7) 0.0272(7) 0.0466(8) -0.0065(5) -0.0068(6) -0.0048(6) C66 0.0340(7) 0.0276(7) 0.0341(7) -0.0084(5) 0.0068(6) -0.0106(5) 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 116.12(10) no N2 C2 N1 116.63(10) no N2 C2 N3 117.54(10) no N1 C2 N3 125.83(11) no C2 N2 C27 123.94(10) no C2 N2 H2 118.0 no C27 N2 H2 118.0 no N2 C27 C21 114.73(10) no N2 C27 H27A 108.6 no C21 C27 H27A 108.6 no N2 C27 H27B 108.6 no C21 C27 H27B 108.6 no H27A C27 H27B 107.6 no C22 C21 C26 118.55(11) no C22 C21 C27 119.33(11) no C26 C21 C27 122.11(10) no C21 C22 C23 120.98(12) no C21 C22 H22 119.5 no C23 C22 H22 119.5 no C24 C23 C22 119.95(12) no C24 C23 H23 120.0 no C22 C23 H23 120.0 no C23 C24 C25 119.68(12) no C23 C24 H24 120.2 no C25 C24 H24 120.2 no C24 C25 C26 120.23(12) no C24 C25 H25 119.9 no C26 C25 H25 119.9 no C25 C26 C21 120.61(12) no C25 C26 H26 119.7 no C21 C26 H26 119.7 no C4 N3 C2 115.00(10) no N3 C4 O4 118.75(10) no N3 C4 C5 124.90(11) no O4 C4 C5 116.34(10) no C4 O4 C47 116.87(9) no O4 C47 C41 106.83(10) no O4 C47 H47A 110.4 no C41 C47 H47A 110.4 no O4 C47 H47B 110.4 no C41 C47 H47B 110.4 no H47A C47 H47B 108.6 no C42 C41 C46 118.45(12) no C42 C41 C47 121.14(12) no C46 C41 C47 120.41(12) no C41 C42 C43 121.02(13) no C41 C42 H42 119.5 no C43 C42 H42 119.5 no C44 C43 C42 120.14(14) no C44 C43 H43 119.9 no C42 C43 H43 119.9 no C45 C44 C43 119.33(13) no C45 C44 H44 120.3 no C43 C44 H44 120.3 no C44 C45 C46 120.80(13) no C44 C45 H45 119.6 no C46 C45 H45 119.6 no C41 C46 C45 120.26(13) no C41 C46 H46 119.9 no C45 C46 H46 119.9 no C6 C5 C4 114.53(11) no C6 C5 H5 122.7 no C4 C5 H5 122.7 no N1 C6 O6 112.10(10) no N1 C6 C5 123.60(11) no O6 C6 C5 124.24(10) no C6 O6 C67 116.37(9) no O6 C67 C61 109.25(10) no O6 C67 H67A 109.8 no C61 C67 H67A 109.8 no O6 C67 H67B 109.8 no C61 C67 H67B 109.8 no H67A C67 H67B 108.3 no C62 C61 C66 118.87(11) no C62 C61 C67 120.71(12) no C66 C61 C67 120.39(12) no C61 C62 C63 120.57(12) no C61 C62 H62 119.7 no C63 C62 H62 119.7 no C64 C63 C62 120.07(12) no C64 C63 H63 120.0 no C62 C63 H63 120.0 no C63 C64 C65 119.89(12) no C63 C64 H64 120.1 no C65 C64 H64 120.1 no C64 C65 C66 119.99(12) no C64 C65 H65 120.0 no C66 C65 H65 120.0 no C65 C66 C61 120.59(12) no C65 C66 H66 119.7 no C61 C66 H66 119.7 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 . 1.3466(15) y C2 N3 . 1.3582(15) y N3 C4 . 1.3227(15) y C4 C5 . 1.3925(17) y C5 C6 . 1.3863(16) y C6 N1 . 1.3342(15) y C2 N2 . 1.3424(15) y N2 C27 . 1.4495(15) y C4 O4 . 1.3516(14) y O4 C47 . 1.4522(14) y C6 O6 . 1.3530(14) y O6 C67 . 1.4470(15) y N2 H2 . 0.8800 no C27 C21 . 1.5172(17) no C27 H27A . 0.9900 no C27 H27B . 0.9900 no C21 C22 . 1.3886(16) no C21 C26 . 1.3923(17) no C22 C23 . 1.3910(18) no C22 H22 . 0.9500 no C23 C24 . 1.383(2) no C23 H23 . 0.9500 no C24 C25 . 1.3854(19) no C24 H24 . 0.9500 no C25 C26 . 1.3900(18) no C25 H25 . 0.9500 no C26 H26 . 0.9500 no C47 C41 . 1.5042(17) no C47 H47A . 0.9900 no C47 H47B . 0.9900 no C41 C42 . 1.3831(19) no C41 C46 . 1.3833(19) no C42 C43 . 1.384(2) no C42 H42 . 0.9500 no C43 C44 . 1.377(2) no C43 H43 . 0.9500 no C44 C45 . 1.370(2) no C44 H44 . 0.9500 no C45 C46 . 1.390(2) no C45 H45 . 0.9500 no C46 H46 . 0.9500 no C5 H5 . 0.9500 no C67 C61 . 1.5005(17) no C67 H67A . 0.9900 no C67 H67B . 0.9900 no C61 C62 . 1.3872(18) no C61 C66 . 1.3894(18) no C62 C63 . 1.3872(18) no C62 H62 . 0.9500 no C63 C64 . 1.381(2) no C63 H63 . 0.9500 no C64 C65 . 1.382(2) no C64 H64 . 0.9500 no C65 C66 . 1.3871(19) no C65 H65 . 0.9500 no C66 H66 . 0.9500 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 H2 N1 2_756 0.88 2.13 2.997(2) 170 y C66 H66 N1 1_655 0.95 2.58 3.516(2) 170 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 C27 N2 C2 N3 -3.0(2) y C47 O4 C4 N3 1.1(2) y C67 O6 C6 C5 2.1(2) y