#------------------------------------------------------------------------------ #$Date: 2011-09-28 17:24:46 +0300 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/31/2013184.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2013184 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2003 _journal_volume 59 _journal_page_first o9 _journal_page_last o13 _publ_section_title ; Hydrogen bonding in 2-amino-4-methoxy-6-methylpyrimidine, 2-benzylamino-4-benzyloxy-6-methylpyrimidine and 4-benzylamino-2,6-bis(benzyloxy)pyrimidine: \p-stacked chains of fused R^2^~2~(8) rings, and centrosymmetric R^2^~2~(8) dimers ; _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _[local]_cod_cif_authors_sg_H-M 'P 21/c' loop_ _publ_author_name 'Glidewell, Christopher' 'Low, John N.' 'Melguizo, Manuel' 'Quesada, Antonio' _chemical_formula_moiety 'C25 H23 N3 O2' _chemical_formula_sum 'C25 H23 N3 O2' _chemical_formula_iupac 'C25 H23 N3 O2' _chemical_formula_weight 397.46 _symmetry_cell_setting monoclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.6056(2) _cell_length_b 18.2446(5) _cell_length_c 20.6480(8) _cell_angle_alpha 90.00 _cell_angle_beta 100.9650(10) _cell_angle_gamma 90.00 _cell_volume 2073.16(12) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _exptl_crystal_density_diffrn 1.273 _diffrn_ambient_temperature 120(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 1.0799(2) 0.40310(8) 0.62780(7) 0.0219(4) Uani d . 1 . . N C2 0.8732(3) 0.40173(10) 0.58335(8) 0.0212(4) Uani d . 1 . . C C21 0.6951(3) 0.21091(10) 0.58460(9) 0.0241(4) Uani d . 1 . . C C22 0.5821(3) 0.17710(11) 0.63056(9) 0.0309(5) Uani d . 1 . . C C23 0.4128(4) 0.12225(12) 0.61258(10) 0.0364(5) Uani d . 1 . . C C24 0.3545(3) 0.10049(11) 0.54768(10) 0.0348(5) Uani d . 1 . . C C25 0.4638(4) 0.13319(12) 0.50108(10) 0.0408(5) Uani d . 1 . . C C26 0.6342(4) 0.18797(11) 0.51939(10) 0.0369(5) Uani d . 1 . . C C27 0.8704(3) 0.27252(10) 0.60378(9) 0.0270(4) Uani d . 1 . . C O2 0.7589(2) 0.33668(7) 0.57016(6) 0.0253(3) Uani d . 1 . . O N3 0.7552(2) 0.45599(8) 0.54943(7) 0.0213(3) Uani d . 1 . . N N4 0.7413(2) 0.57865(8) 0.52500(7) 0.0221(4) Uani d . 1 . . N C4 0.8585(3) 0.52300(10) 0.56023(8) 0.0207(4) Uani d . 1 . . C C41 0.7785(3) 0.68374(10) 0.60319(9) 0.0226(4) Uani d . 1 . . C C42 0.6246(4) 0.64959(12) 0.63845(10) 0.0387(5) Uani d . 1 . . C C43 0.5943(4) 0.67636(12) 0.69907(11) 0.0431(6) Uani d . 1 . . C C44 0.7198(3) 0.73721(11) 0.72561(10) 0.0331(5) Uani d . 1 . . C C45 0.8752(4) 0.77118(12) 0.69155(10) 0.0408(6) Uani d . 1 . . C C46 0.9047(4) 0.74430(12) 0.63086(10) 0.0369(5) Uani d . 1 . . C C47 0.8116(3) 0.65442(10) 0.53648(9) 0.0241(4) Uani d . 1 . . C C5 1.0748(3) 0.53260(10) 0.60609(8) 0.0217(4) Uani d . 1 . . C C6 1.1744(3) 0.47034(10) 0.63757(8) 0.0219(4) Uani d . 1 . . C C61 1.6809(3) 0.44110(10) 0.77412(9) 0.0232(4) Uani d . 1 . . C C62 1.7009(3) 0.41495(11) 0.83814(9) 0.0279(4) Uani d . 1 . . C C63 1.8945(3) 0.43636(11) 0.88699(10) 0.0321(5) Uani d . 1 . . C C64 2.0670(3) 0.48398(11) 0.87229(10) 0.0328(5) Uani d . 1 . . C C65 2.0476(3) 0.51062(11) 0.80854(10) 0.0325(5) Uani d . 1 . . C C66 1.8547(3) 0.48915(11) 0.75981(9) 0.0282(5) Uani d . 1 . . C C67 1.4741(3) 0.41581(10) 0.72120(9) 0.0254(4) Uani d . 1 . . C O6 1.3804(2) 0.47949(7) 0.68340(6) 0.0260(3) Uani d . 1 . . O H22 0.6217 0.1919 0.6754 0.037 Uiso calc R 1 . . H H23 0.3369 0.0997 0.6448 0.044 Uiso calc R 1 . . H H24 0.2383 0.0627 0.5351 0.042 Uiso calc R 1 . . H H25 0.4226 0.1183 0.4563 0.049 Uiso calc R 1 . . H H26 0.7103 0.2101 0.4870 0.044 Uiso calc R 1 . . H H27A 0.9010 0.2800 0.6521 0.032 Uiso calc R 1 . . H H27B 1.0269 0.2618 0.5902 0.032 Uiso calc R 1 . . H H4 0.6162 0.5684 0.4936 0.027 Uiso calc R 1 . . H H42 0.5381 0.6071 0.6209 0.046 Uiso calc R 1 . . H H43 0.4860 0.6525 0.7224 0.052 Uiso calc R 1 . . H H44 0.6990 0.7556 0.7672 0.040 Uiso calc R 1 . . H H45 0.9631 0.8133 0.7096 0.049 Uiso calc R 1 . . H H46 1.0142 0.7681 0.6079 0.044 Uiso calc R 1 . . H H47A 0.7144 0.6848 0.5014 0.029 Uiso calc R 1 . . H H47B 0.9845 0.6597 0.5330 0.029 Uiso calc R 1 . . H H5 1.1482 0.5794 0.6149 0.026 Uiso calc R 1 . . H H62 1.5817 0.3823 0.8486 0.033 Uiso calc R 1 . . H H63 1.9077 0.4181 0.9306 0.039 Uiso calc R 1 . . H H64 2.1993 0.4986 0.9057 0.039 Uiso calc R 1 . . H H65 2.1664 0.5436 0.7983 0.039 Uiso calc R 1 . . H H66 1.8418 0.5076 0.7162 0.034 Uiso calc R 1 . . H H67A 1.5324 0.3792 0.6924 0.031 Uiso calc R 1 . . H H67B 1.3454 0.3930 0.7413 0.031 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 0.0233(8) 0.0220(9) 0.0196(8) -0.0025(6) 0.0022(6) -0.0002(7) C2 0.0234(9) 0.0219(11) 0.0183(9) -0.0022(8) 0.0041(7) -0.0021(8) C21 0.0251(9) 0.0222(11) 0.0240(10) 0.0016(8) 0.0020(7) 0.0013(8) C22 0.0343(10) 0.0342(13) 0.0235(10) -0.0032(9) 0.0038(8) 0.0020(9) C23 0.0379(11) 0.0399(14) 0.0318(12) -0.0094(10) 0.0074(9) 0.0095(10) C24 0.0341(11) 0.0298(13) 0.0368(12) -0.0104(9) -0.0027(9) 0.0053(10) C25 0.0557(13) 0.0395(14) 0.0258(11) -0.0172(11) 0.0047(9) -0.0061(10) C26 0.0477(12) 0.0355(13) 0.0299(11) -0.0157(10) 0.0132(9) -0.0014(10) C27 0.0309(10) 0.0222(11) 0.0254(10) -0.0002(8) -0.0003(8) 0.0041(8) O2 0.0276(6) 0.0174(7) 0.0279(7) -0.0024(5) -0.0024(5) 0.0011(6) N3 0.0233(7) 0.0193(9) 0.0205(8) -0.0029(6) 0.0018(6) -0.0007(7) N4 0.0256(8) 0.0197(9) 0.0182(8) -0.0026(6) -0.0033(6) -0.0008(6) C4 0.0235(9) 0.0238(11) 0.0156(9) -0.0010(8) 0.0056(7) -0.0009(8) C41 0.0212(8) 0.0214(11) 0.0245(10) 0.0021(7) 0.0023(7) 0.0010(8) C42 0.0360(11) 0.0393(14) 0.0446(13) -0.0150(9) 0.0175(9) -0.0167(11) C43 0.0460(12) 0.0454(15) 0.0452(13) -0.0160(10) 0.0270(10) -0.0144(11) C44 0.0412(11) 0.0328(13) 0.0266(11) -0.0013(9) 0.0101(9) -0.0066(9) C45 0.0507(13) 0.0357(14) 0.0376(13) -0.0175(10) 0.0124(10) -0.0142(10) C46 0.0460(12) 0.0350(13) 0.0332(12) -0.0182(10) 0.0163(9) -0.0051(10) C47 0.0285(9) 0.0208(11) 0.0221(10) -0.0014(8) 0.0030(7) 0.0004(8) C5 0.0229(9) 0.0204(11) 0.0219(9) -0.0029(7) 0.0044(7) -0.0008(8) C6 0.0215(9) 0.0263(11) 0.0174(9) -0.0024(8) 0.0026(7) -0.0010(8) C61 0.0231(9) 0.0209(11) 0.0244(10) 0.0052(8) 0.0015(7) -0.0029(8) C62 0.0287(10) 0.0261(12) 0.0278(11) 0.0029(8) 0.0029(8) 0.0025(8) C63 0.0376(11) 0.0278(12) 0.0269(11) 0.0082(9) -0.0040(8) -0.0005(9) C64 0.0263(10) 0.0318(13) 0.0353(12) 0.0056(9) -0.0068(8) -0.0055(9) C65 0.0252(10) 0.0354(13) 0.0372(12) -0.0023(8) 0.0062(8) -0.0062(10) C66 0.0258(9) 0.0330(12) 0.0258(10) 0.0024(8) 0.0052(8) -0.0019(9) C67 0.0272(10) 0.0226(11) 0.0245(10) 0.0015(8) -0.0002(7) 0.0025(8) O6 0.0241(6) 0.0248(8) 0.0254(7) -0.0035(5) -0.0048(5) 0.0023(6) 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 . 1.335(2) y C2 N3 . 1.316(2) y N3 C4 . 1.353(2) y C4 C5 . 1.400(2) y C5 C6 . 1.374(2) y C6 N1 . 1.336(2) y C2 O2 . 1.352(2) y O2 C27 . 1.441(2) y C4 N4 . 1.345(2) y N4 C47 . 1.445(2) y C6 O6 . 1.357(2) y O6 C67 . 1.442(2) y C21 C22 . 1.382(3) no C21 C26 . 1.389(3) no C21 C27 . 1.496(3) no C22 C23 . 1.380(3) no C22 H22 . 0.95 no C23 C24 . 1.376(3) no C23 H23 . 0.95 no C24 C25 . 1.372(3) no C24 H24 . 0.95 no C25 C26 . 1.384(3) no C25 H25 . 0.95 no C26 H26 . 0.95 no C27 H27A . 0.99 no C27 H27B . 0.99 no N4 H4 . 0.88 no C41 C46 . 1.376(3) no C41 C42 . 1.379(3) no C41 C47 . 1.522(3) no C42 C43 . 1.384(3) no C42 H42 . 0.95 no C43 C44 . 1.371(3) no C43 H43 . 0.95 no C44 C45 . 1.368(3) no C44 H44 . 0.95 no C45 C46 . 1.384(3) no C45 H45 . 0.95 no C46 H46 . 0.95 no C47 H47A . 0.99 no C47 H47B . 0.99 no C5 H5 . 0.95 no C61 C66 . 1.384(3) no C61 C62 . 1.390(2) no C61 C67 . 1.506(2) no C62 C63 . 1.389(3) no C62 H62 . 0.95 no C63 C64 . 1.376(3) no C63 H63 . 0.95 no C64 C65 . 1.388(3) no C64 H64 . 0.95 no C65 C66 . 1.386(3) no C65 H65 . 0.95 no C66 H66 . 0.95 no C67 H67A . 0.99 no C67 H67B . 0.99 no _cod_database_code 2013184