#------------------------------------------------------------------------------ #$Date: 2009-11-16 03:43:51 +0200 (Mon, 16 Nov 2009) $ #$Revision: 853 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2013183.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_2013183 _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 'C19 H19 N3 O' _chemical_formula_sum 'C19 H19 N3 O' _chemical_formula_iupac 'C19 H19 N3 O' _chemical_formula_weight 305.38 _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 5.8932(2) _cell_length_b 18.2849(7) _cell_length_c 15.1175(7) _cell_angle_alpha 90.00 _cell_angle_beta 98.704(2) _cell_angle_gamma 90.00 _cell_volume 1610.25(11) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _exptl_crystal_density_diffrn 1.260 _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 0.3786(2) 0.41128(6) 0.54274(8) 0.0248(3) Uani d . 1 . . N C2 0.2046(2) 0.42351(8) 0.47591(9) 0.0235(3) Uani d . 1 . . C C21 0.0557(2) 0.45877(7) 0.26654(10) 0.0247(3) Uani d . 1 . . C C22 0.2481(3) 0.46390(8) 0.22397(11) 0.0324(4) Uani d . 1 . . C C23 0.2572(3) 0.42769(9) 0.14406(12) 0.0360(4) Uani d . 1 . . C C24 0.0755(3) 0.38511(9) 0.10589(11) 0.0356(4) Uani d . 1 . . C C25 -0.1153(3) 0.37827(9) 0.14836(11) 0.0352(4) Uani d . 1 . . C C26 -0.1248(3) 0.41521(8) 0.22793(10) 0.0299(4) Uani d . 1 . . C C27 0.0400(3) 0.50143(8) 0.35103(10) 0.0278(4) Uani d . 1 . . C N2 0.2185(2) 0.48339(7) 0.42474(8) 0.0279(3) Uani d . 1 . . N N3 0.0163(2) 0.38143(6) 0.45427(8) 0.0247(3) Uani d . 1 . . N O4 -0.17951(17) 0.27910(6) 0.48822(7) 0.0299(3) Uani d . 1 . . O C4 0.0030(2) 0.32420(8) 0.50671(10) 0.0255(3) Uani d . 1 . . C C41 -0.5105(3) 0.23401(8) 0.39309(10) 0.0281(4) Uani d . 1 . . C C42 -0.7263(3) 0.24832(10) 0.34582(11) 0.0365(4) Uani d . 1 . . C C43 -0.8854(3) 0.19269(11) 0.32694(13) 0.0462(5) Uani d . 1 . . C C44 -0.8316(3) 0.12265(11) 0.35528(13) 0.0456(5) Uani d . 1 . . C C45 -0.6168(3) 0.10718(10) 0.40146(12) 0.0417(4) Uani d . 1 . . C C46 -0.4554(3) 0.16270(9) 0.42006(10) 0.0337(4) Uani d . 1 . . C C47 -0.3399(3) 0.29512(8) 0.40894(10) 0.0288(4) Uani d . 1 . . C C5 0.1674(3) 0.30720(8) 0.57925(10) 0.0279(4) Uani d . 1 . . C C6 0.3570(2) 0.35210(8) 0.59406(10) 0.0252(3) Uani d . 1 . . C C61 0.5501(3) 0.33671(9) 0.66774(10) 0.0307(4) Uani d . 1 . . C H22 0.3752 0.4926 0.2500 0.039 Uiso calc R 1 . . H H23 0.3893 0.4323 0.1154 0.043 Uiso calc R 1 . . H H24 0.0813 0.3606 0.0508 0.043 Uiso calc R 1 . . H H25 -0.2401 0.3483 0.1231 0.042 Uiso calc R 1 . . H H26 -0.2572 0.4106 0.2564 0.036 Uiso calc R 1 . . H H27A 0.0488 0.5543 0.3379 0.033 Uiso calc R 1 . . H H27B -0.1114 0.4920 0.3696 0.033 Uiso calc R 1 . . H H2 0.3389 0.5122 0.4364 0.034 Uiso calc R 1 . . H H42 -0.7653 0.2967 0.3262 0.044 Uiso calc R 1 . . H H43 -1.0325 0.2030 0.2942 0.055 Uiso calc R 1 . . H H44 -0.9424 0.0848 0.3431 0.055 Uiso calc R 1 . . H H45 -0.5792 0.0586 0.4206 0.050 Uiso calc R 1 . . H H46 -0.3069 0.1519 0.4513 0.040 Uiso calc R 1 . . H H47A -0.2574 0.3002 0.3569 0.035 Uiso calc R 1 . . H H47B -0.4200 0.3417 0.4167 0.035 Uiso calc R 1 . . H H5 0.1503 0.2666 0.6169 0.034 Uiso calc R 1 . . H H61A 0.6953 0.3363 0.6436 0.046 Uiso calc R 1 . . H H61B 0.5263 0.2889 0.6943 0.046 Uiso calc R 1 . . H H61C 0.5553 0.3747 0.7137 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 0.0253(7) 0.0272(7) 0.0218(6) -0.0004(5) 0.0033(5) -0.0019(5) C2 0.0269(8) 0.0232(7) 0.0208(8) 0.0007(6) 0.0049(6) -0.0046(6) C21 0.0272(8) 0.0201(7) 0.0250(8) 0.0036(6) -0.0016(6) 0.0030(6) C22 0.0288(8) 0.0305(8) 0.0371(9) -0.0018(7) 0.0024(7) -0.0029(7) C23 0.0345(9) 0.0371(9) 0.0381(9) 0.0021(7) 0.0111(7) -0.0019(8) C24 0.0447(10) 0.0342(9) 0.0273(9) 0.0017(7) 0.0031(7) -0.0033(7) C25 0.0360(9) 0.0367(9) 0.0306(9) -0.0086(7) -0.0027(7) -0.0025(7) C26 0.0285(8) 0.0334(8) 0.0269(8) -0.0012(7) 0.0015(7) 0.0021(7) C27 0.0284(8) 0.0263(8) 0.0276(8) 0.0029(6) 0.0007(7) 0.0006(7) N2 0.0304(7) 0.0265(7) 0.0249(7) -0.0035(5) -0.0019(6) 0.0019(5) N3 0.0255(7) 0.0252(7) 0.0235(7) -0.0013(5) 0.0038(5) -0.0032(5) O4 0.0292(6) 0.0350(6) 0.0240(6) -0.0090(5) -0.0008(4) 0.0001(5) C4 0.0267(8) 0.0270(8) 0.0230(8) -0.0047(6) 0.0049(6) -0.0044(6) C41 0.0276(8) 0.0355(9) 0.0222(8) -0.0017(7) 0.0064(6) -0.0065(7) C42 0.0305(9) 0.0447(10) 0.0341(9) 0.0032(7) 0.0038(7) -0.0118(8) C43 0.0280(9) 0.0670(13) 0.0432(11) -0.0039(9) 0.0045(8) -0.0251(10) C44 0.0406(11) 0.0589(13) 0.0395(10) -0.0240(9) 0.0127(8) -0.0231(9) C45 0.0529(12) 0.0380(9) 0.0357(10) -0.0135(8) 0.0113(9) -0.0065(8) C46 0.0374(9) 0.0391(9) 0.0243(8) -0.0047(7) 0.0039(7) -0.0025(7) C47 0.0277(8) 0.0327(9) 0.0252(8) -0.0015(6) 0.0018(6) -0.0024(7) C5 0.0328(9) 0.0287(8) 0.0221(8) -0.0039(6) 0.0036(7) 0.0018(6) C6 0.0284(8) 0.0276(8) 0.0202(7) 0.0001(6) 0.0057(6) -0.0028(6) C61 0.0300(8) 0.0360(9) 0.0254(8) -0.0053(7) 0.0017(7) 0.0031(7) 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 . 1.3447(19) y C2 N3 . 1.3493(18) y N3 C4 . 1.3223(19) y C4 C5 . 1.384(2) y C5 C6 . 1.377(2) y C6 N1 . 1.3486(19) y C2 N2 . 1.3501(19) y N2 C27 . 1.450(2) y C4 O4 . 1.3505(18) y O4 C47 . 1.4398(19) y C6 C61 . 1.494(2) y C21 C26 . 1.385(2) no C21 C22 . 1.389(2) no C21 C27 . 1.511(2) no C22 C23 . 1.386(2) no C22 H22 . 0.95 no C23 C24 . 1.378(2) no C23 H23 . 0.95 no C24 C25 . 1.382(2) no C24 H24 . 0.95 no C25 C26 . 1.388(2) no C25 H25 . 0.95 no C26 H26 . 0.95 no C27 H27A . 0.99 no C27 H27B . 0.99 no N2 H2 . 0.88 no C41 C42 . 1.386(2) no C41 C46 . 1.390(2) no C41 C47 . 1.498(2) no C42 C43 . 1.383(2) no C42 H42 . 0.95 no C43 C44 . 1.372(3) no C43 H43 . 0.95 no C44 C45 . 1.379(3) no C44 H44 . 0.95 no C45 C46 . 1.391(2) 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 H61A . 0.98 no C61 H61B . 0.98 no C61 H61C . 0.98 no