#------------------------------------------------------------------------------ #$Date: 2008-06-20 14:44:24 +0100 (Fri, 20 Jun 2008) $ #$Revision: 397 $ #$URL: svn://www.crystallography.net/cod/cif/2/2103868.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_2103868 loop_ _publ_author_name 'Melguizo, Manuel' 'Quesada, Antonio' 'Low, John N.' 'Glidewell, Christopher' _publ_section_title ; Supramolecular structures of N^4^-substituted 2,4-diamino-6-benzyloxy-5-nitrosopyrimidines ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 263 _journal_page_last 276 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety 'C12 H13 N5 O2' _chemical_formula_sum 'C12 H13 N5 O2' _chemical_formula_weight 259.267 _chemical_name_systematic ; 2-Amino-6-benzyloxy-4-(N-methylamino)-5-nitrosopyrimidine ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.1122(2) _cell_length_b 7.3873(2) _cell_length_c 23.3867(7) _cell_measurement_reflns_used 1649 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.47 _cell_measurement_theta_min 2.99 _cell_volume 1228.74(6) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'Kappa-CCD server software (Nonius, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2002)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997a) and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997a)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997b)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type Kappa-CCD _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 0.060 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 6981 _diffrn_reflns_theta_full 27.47 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_min 2.99 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_correction_T_min 0.954 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details 'DENZO-SMN (Otwinowski & Minor, 1997)' _exptl_crystal_colour pink _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 544 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.176 _refine_diff_density_min -0.236 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 1649 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.091 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0392 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0467P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0843 _refine_ls_wR_factor_ref 0.0902 _reflns_number_gt 1323 _reflns_number_total 1649 _reflns_threshold_expression >2\s(I) _[local]_cod_data_source_file na0145.cif _[local]_cod_data_source_block 1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' 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_ _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_type_symbol N1 0.7669(3) 1.1531(2) 0.13328(8) 0.0226(4) Uani d . 1 N C2 0.8858(3) 1.2910(3) 0.14977(10) 0.0220(5) Uani d . 1 C N2 0.8267(3) 1.4559(3) 0.13741(9) 0.0316(5) Uani d . 1 N N3 1.0523(2) 1.2758(2) 0.17588(8) 0.0226(4) Uani d . 1 N C4 1.1051(3) 1.1086(3) 0.19092(9) 0.0198(5) Uani d . 1 C N4 1.2650(3) 1.0868(2) 0.21909(8) 0.0248(4) Uani d . 1 N C41 1.3894(3) 1.2361(3) 0.23419(11) 0.0303(6) Uani d . 1 C C5 0.9949(3) 0.9511(3) 0.17556(9) 0.0193(5) Uani d . 1 C N5 1.0382(3) 0.7757(2) 0.18412(8) 0.0235(4) Uani d . 1 N O5 1.1890(2) 0.7408(2) 0.21219(7) 0.0271(4) Uani d . 1 O C6 0.8244(3) 0.9904(3) 0.14496(9) 0.0194(5) Uani d . 1 C C61 0.5036(3) 0.7082(3) 0.06605(9) 0.0224(5) Uani d . 1 C C62 0.3886(3) 0.5793(3) 0.09145(10) 0.0256(5) Uani d . 1 C C63 0.3519(3) 0.4165(3) 0.06323(11) 0.0294(6) Uani d . 1 C C64 0.4296(3) 0.3826(3) 0.01079(10) 0.0320(6) Uani d . 1 C C65 0.5449(3) 0.5104(3) -0.01465(11) 0.0311(6) Uani d . 1 C C66 0.5817(3) 0.6723(3) 0.01291(10) 0.0271(6) Uani d . 1 C C67 0.5514(3) 0.8825(3) 0.09596(10) 0.0273(5) Uani d . 1 C O6 0.7229(2) 0.84726(19) 0.12848(6) 0.0239(4) Uani d . 1 O H2A 0.8962 1.5503 0.1464 0.038 Uiso calc R 1 H H2B 0.7178 1.4714 0.1202 0.038 Uiso calc R 1 H H4 1.2978 0.9765 0.2292 0.030 Uiso calc R 1 H H41A 1.4801 1.2559 0.2033 0.045 Uiso calc R 1 H H41B 1.4569 1.2066 0.2695 0.045 Uiso calc R 1 H H41C 1.3150 1.3462 0.2400 0.045 Uiso calc R 1 H H62 0.3350 0.6019 0.1280 0.031 Uiso calc R 1 H H63 0.2725 0.3288 0.0805 0.035 Uiso calc R 1 H H64 0.4045 0.2714 -0.0082 0.038 Uiso calc R 1 H H65 0.5989 0.4868 -0.0511 0.037 Uiso calc R 1 H H66 0.6610 0.7595 -0.0047 0.033 Uiso calc R 1 H H67A 0.5725 0.9804 0.0678 0.033 Uiso calc R 1 H H67B 0.4481 0.9190 0.1219 0.033 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 0.0226(10) 0.0180(9) 0.0272(10) 0.0025(8) -0.0019(9) -0.0012(8) C2 0.0255(11) 0.0177(11) 0.0227(12) 0.0016(9) 0.0014(10) -0.0019(10) N2 0.0326(12) 0.0164(10) 0.0458(13) 0.0013(8) -0.0126(10) -0.0008(9) N3 0.0227(10) 0.0190(9) 0.0262(10) -0.0009(8) -0.0021(8) -0.0010(8) C4 0.0190(11) 0.0212(12) 0.0192(11) -0.0002(9) 0.0005(9) -0.0031(9) N4 0.0214(10) 0.0229(10) 0.0300(11) 0.0015(8) -0.0030(9) -0.0020(8) C41 0.0218(12) 0.0347(14) 0.0342(14) -0.0071(11) -0.0027(10) -0.0063(11) C5 0.0201(11) 0.0165(11) 0.0214(11) 0.0010(9) -0.0003(10) -0.0009(9) N5 0.0210(10) 0.0255(10) 0.0239(10) 0.0027(8) -0.0020(8) 0.0004(8) O5 0.0233(8) 0.0268(9) 0.0311(9) 0.0058(7) -0.0063(7) 0.0002(7) C6 0.0201(11) 0.0174(11) 0.0208(11) 0.0006(9) -0.0005(9) -0.0026(9) C61 0.0189(11) 0.0210(12) 0.0273(13) 0.0026(9) -0.0079(10) -0.0004(9) C62 0.0247(13) 0.0278(12) 0.0245(12) 0.0016(10) -0.0005(10) 0.0005(10) C63 0.0289(13) 0.0264(13) 0.0329(14) -0.0079(10) -0.0030(12) 0.0048(11) C64 0.0381(15) 0.0242(13) 0.0338(14) -0.0017(11) -0.0063(12) -0.0060(11) C65 0.0308(14) 0.0378(14) 0.0245(12) 0.0026(11) 0.0011(11) -0.0044(11) C66 0.0221(12) 0.0302(14) 0.0290(13) -0.0037(10) -0.0014(11) 0.0039(10) C67 0.0228(13) 0.0226(12) 0.0365(13) 0.0034(9) -0.0090(11) -0.0042(10) O6 0.0229(8) 0.0173(8) 0.0315(9) 0.0004(6) -0.0101(7) -0.0012(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C6 1.299(3) no N1 C2 1.379(3) no C2 N2 1.320(3) no C2 N3 1.337(3) no N2 H2A 0.88 no N2 H2B 0.88 no N3 C4 1.338(3) no C4 N4 1.324(3) no C4 C5 1.448(3) no N4 C41 1.457(3) no N4 H4 0.88 no C41 H41A 0.98 no C41 H41B 0.98 no C41 H41C 0.98 no C5 N5 1.347(3) no C5 C6 1.438(3) no N5 O5 1.283(2) no C6 O6 1.337(2) no C61 C66 1.387(3) no C61 C62 1.388(3) no C61 C67 1.504(3) no C62 C63 1.396(3) no C62 H62 0.95 no C63 C64 1.368(3) no C63 H63 0.95 no C64 C65 1.385(3) no C64 H64 0.95 no C65 C66 1.384(3) no C65 H65 0.95 no C66 H66 0.95 no C67 O6 1.461(3) no C67 H67A 0.99 no C67 H67B 0.99 no 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 115.56(18) no N2 C2 N3 117.4(2) no N2 C2 N1 115.1(2) no N3 C2 N1 127.51(18) no C2 N2 H2A 120.0 no C2 N2 H2B 120.0 no H2A N2 H2B 120.0 no C2 N3 C4 116.51(18) no N4 C4 N3 118.95(19) no N4 C4 C5 119.37(19) no N3 C4 C5 121.66(19) no C4 N4 C41 123.37(18) no C4 N4 H4 118.3 no C41 N4 H4 118.3 no N4 C41 H41A 109.5 no N4 C41 H41B 109.5 no H41A C41 H41B 109.5 no N4 C41 H41C 109.5 no H41A C41 H41C 109.5 no H41B C41 H41C 109.5 no N5 C5 C6 117.45(19) no N5 C5 C4 127.8(2) no C6 C5 C4 114.69(18) no O5 N5 C5 117.39(19) no N1 C6 O6 120.08(18) no N1 C6 C5 123.85(18) no O6 C6 C5 116.07(18) no C66 C61 C62 119.2(2) no C66 C61 C67 119.3(2) no C62 C61 C67 121.4(2) no C61 C62 C63 119.9(2) no C61 C62 H62 120.0 no C63 C62 H62 120.0 no C64 C63 C62 120.4(2) no C64 C63 H63 119.8 no C62 C63 H63 119.8 no C63 C64 C65 119.9(2) no C63 C64 H64 120.0 no C65 C64 H64 120.0 no C66 C65 C64 120.1(2) no C66 C65 H65 120.0 no C64 C65 H65 120.0 no C65 C66 C61 120.5(2) no C65 C66 H66 119.8 no C61 C66 H66 119.8 no O6 C67 C61 106.16(18) no O6 C67 H67A 110.5 no C61 C67 H67A 110.5 no O6 C67 H67B 110.5 no C61 C67 H67B 110.5 no H67A C67 H67B 108.7 no C6 O6 C67 117.40(16) 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 C6 N1 C2 N2 179.6(2) no C6 N1 C2 N3 0.4(3) no N2 C2 N3 C4 176.4(2) no N1 C2 N3 C4 -4.4(3) no C2 N3 C4 N4 -177.14(19) no C2 N3 C4 C5 4.9(3) no N3 C4 N4 C41 -0.8(3) no C5 C4 N4 C41 177.20(19) no N4 C4 C5 N5 -3.3(3) no N3 C4 C5 N5 174.6(2) no N4 C4 C5 C6 -179.84(19) no N3 C4 C5 C6 -1.9(3) no C6 C5 N5 O5 -178.96(17) no C4 C5 N5 O5 4.6(3) no C2 N1 C6 O6 -177.08(19) no C2 N1 C6 C5 3.1(3) no N5 C5 C6 N1 -179.3(2) no C4 C5 C6 N1 -2.4(3) no N5 C5 C6 O6 0.9(3) no C4 C5 C6 O6 177.79(18) no C66 C61 C62 C63 -0.5(3) no C67 C61 C62 C63 -178.0(2) no C61 C62 C63 C64 0.4(4) no C62 C63 C64 C65 -0.2(4) no C63 C64 C65 C66 0.0(3) no C64 C65 C66 C61 -0.1(3) no C62 C61 C66 C65 0.3(3) no C67 C61 C66 C65 177.9(2) no C66 C61 C67 O6 -87.4(2) no C62 C61 C67 O6 90.2(2) no N1 C6 O6 C67 1.8(3) no C5 C6 O6 C67 -178.41(18) no C61 C67 O6 C6 160.73(19) 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 N4 H4 O5 . 0.88 1.95 2.618(2) 132 y N2 H2A N5 1_565 0.88 2.14 3.006(3) 169 y N2 H2B Cg1 1_565 0.88 2.68 3.516(2) 160 y C62 H62 O5 1_455 0.95 2.45 3.379(3) 165 y C66 H66 Cg1 3_565 0.95 2.73 3.647(2) 163 y