#------------------------------------------------------------------------------ #$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/21/2102146.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_2102146 loop_ _publ_author_name 'Low, John N.' 'Ferguson, George' 'Glidewell, Christopher' _publ_section_title ; N-(6-Amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl) Derivatives of Glycine, Valine, Serine, Threonine and Methionine: Interplay of Molecular, Molecular-electronic and Supramolecular Structures. ; _journal_issue 5 _journal_name_full 'Acta Crystallographica, Section B' _journal_page_first 882 _journal_page_last 892 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C10 H15 N5 O4' _chemical_formula_sum 'C10 H15 N5 O4' _chemical_formula_weight 269.27 _chemical_name_systematic ; N-(6-Amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl) Valine ; _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.9136(6) _cell_length_b 11.2501(6) _cell_length_c 13.0585(12) _cell_measurement_reflns_used 25 _cell_measurement_temperature 294.0(10) _cell_measurement_theta_max 18.93 _cell_measurement_theta_min 9.31 _cell_volume 1309.49(16) _computing_cell_refinement 'SET4 & CELDIM (Enraf-Nonius, 1992)' _computing_data_collection 'CAD4 (Enraf-Nonius, 1992)' _computing_data_reduction 'DATRD2 in NRCVAX96 (Gabe et al., 1989)' _computing_molecular_graphics 'PLATON (Spek, 1999)' _computing_publication_material 'SHELXL97 and WordPerfect macro PREP8 (Ferguson, 1998)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997b)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997a)' _diffrn_ambient_temperature 294.0(10) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .7093 _diffrn_reflns_av_R_equivalents .019 _diffrn_reflns_av_sigmaI/netI .020 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 3011 _diffrn_reflns_theta_full 27.42 _diffrn_reflns_theta_max 27.42 _diffrn_reflns_theta_min 2.38 _diffrn_standards_decay_% .7 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .108 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 1.0000 _exptl_absorpt_correction_type none _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.366 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 568 _exptl_crystal_size_max .42 _exptl_crystal_size_mid .29 _exptl_crystal_size_min .28 _refine_diff_density_max .277 _refine_diff_density_min -.252 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 185 _refine_ls_number_reflns 1738 _refine_ls_number_restraints 7 _refine_ls_restrained_S_all 1.062 _refine_ls_R_factor_all .0567 _refine_ls_R_factor_gt .0440 _refine_ls_shift/su_max .000 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'w=1/[\s^2^(Fo^2^)+(0.0782P)^2^+0.2134P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_ref .1260 _reflns_number_gt 1375 _reflns_number_total 1738 _reflns_threshold_expression >2\s(I) _[local]_cod_data_source_file na0105.cif 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_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 0 -6 -3 3 -2 -1 5 -2 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .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 .2942(3) .44881(18) .0569(2) .0395(5) Uani d . 1 N C2 .1879(3) .4069(2) .1164(2) .0327(5) Uani d . 1 C N3 .0688(3) .47182(18) .15295(18) .0354(5) Uani d . 1 N C3 -.0587(4) .4131(3) .2033(3) .0518(8) Uani d . 1 C C4 .0651(3) .5957(2) .1402(2) .0343(6) Uani d . 1 C O4 -.0350(2) .65428(18) .17899(18) .0496(6) Uani d . 1 O C5 .1853(3) .6450(2) .0781(2) .0342(6) Uani d . 1 C N5 .1884(3) .76300(19) .07436(19) .0422(6) Uani d . 1 N O5 .2906(3) .81031(16) .01713(18) .0518(6) Uani d . 1 O C6 .2927(3) .5647(2) .0315(2) .0345(6) Uani d . 1 C N6 .3960(3) .6015(2) -.0315(2) .0479(6) Uani d . 1 N N2 .1952(3) .29198(18) .14207(18) .0387(5) Uani d . 1 N C21 .3180(3) .2160(2) .1076(2) .0403(6) Uani d . 1 C C211 .2514(3) .0959(2) .0798(2) .0382(6) Uani d . 1 C O21 .3511(3) .02366(18) .0431(3) .0720(8) Uani d . 1 O O22 .1211(2) .07316(18) .0913(2) .0535(6) Uani d . 1 O C22 .4438(4) .2086(4) .1868(3) .0782(12) Uani d D 1 C C23A .4071(6) .1479(7) .2819(4) .085(2) Uani d PD .701(6) C C23B .4475(17) .3014(13) .2689(11) .099(6) Uiso d PD .299(6) C C24A .5920(6) .1769(9) .1466(6) .134(4) Uani d PD .701(6) C C24B .5334(12) .3198(7) .1977(9) .057(3) Uiso d PD .299(6) C H3A -.1344 .4710 .2189 .078 Uiso calc R 1 H H3B -.0252 .3761 .2655 .078 Uiso calc R 1 H H3C -.0996 .3538 .1585 .078 Uiso calc R 1 H H6A .4613 .5523 -.0550 .057 Uiso calc R 1 H H6B .3989 .6750 -.0496 .057 Uiso calc R 1 H H2 .1257 .2621 .1799 .046 Uiso calc R 1 H H21 .3141 -.0469 .0400 .108 Uiso calc R 1 H H21A .3598 .2509 .0451 .048 Uiso calc R 1 H H22A .4560 .2916 .2081 .094 Uiso d PR .701(6) H H22B .4933 .1322 .1993 .094 Uiso d PR .299(6) H H23A .3264 .1888 .3154 .127 Uiso calc PR .350(3) H H23B .4935 .1472 .3258 .127 Uiso calc PR .350(3) H H23C .3773 .0677 .2672 .127 Uiso calc PR .350(3) H H23D .4717 .0803 .2902 .127 Uiso calc PR .350(3) H H23E .3046 .1220 .2799 .127 Uiso calc PR .350(3) H H23F .4208 .2014 .3384 .127 Uiso calc PR .350(3) H H23G .4858 .3743 .2411 .148 Uiso calc PR .150(3) H H23H .5113 .2753 .3237 .148 Uiso calc PR .150(3) H H23I .3479 .3141 .2945 .148 Uiso calc PR .150(3) H H23J .4108 .2681 .3318 .148 Uiso calc PR .150(3) H H23K .3854 .3672 .2492 .148 Uiso calc PR .150(3) H H23L .5488 .3283 .2783 .148 Uiso calc PR .150(3) H H24A .6195 .2316 .0934 .202 Uiso calc PR .350(3) H H24B .5889 .0977 .1193 .202 Uiso calc PR .350(3) H H24C .6647 .1805 .2008 .202 Uiso calc PR .350(3) H H24D .6292 .1083 .1822 .202 Uiso calc PR .350(3) H H24E .6598 .2422 .1563 .202 Uiso calc PR .350(3) H H24F .5840 .1593 .0749 .202 Uiso calc PR .350(3) H H24G .5387 .3595 .1327 .086 Uiso calc PR .150(3) H H24H .6328 .3004 .2204 .086 Uiso calc PR .150(3) H H24I .4863 .3710 .2469 .086 Uiso calc PR .150(3) H H24J .5665 .3277 .2673 .086 Uiso calc PR .150(3) H H24K .4724 .3869 .1796 .086 Uiso calc PR .150(3) H H24L .6189 .3162 .1531 .086 Uiso calc PR .150(3) 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 .0406(12) .0186(9) .0593(13) .0038(9) .0087(12) -.0018(9) C2 .0363(12) .0196(10) .0422(12) .0000(10) -.0019(12) -.0026(9) N3 .0389(12) .0211(9) .0462(12) .0007(9) .0056(11) -.0011(9) C3 .0519(17) .0344(15) .069(2) .0009(14) .0196(17) .0018(14) C4 .0374(13) .0225(11) .0429(13) .0049(11) -.0009(12) -.0031(10) O4 .0512(12) .0324(10) .0653(14) .0093(10) .0162(11) -.0001(10) C5 .0407(14) .0201(10) .0419(13) .0033(11) .0013(13) -.0036(10) N5 .0512(14) .0220(10) .0534(13) .0044(10) .0061(13) -.0013(9) O5 .0677(14) .0195(8) .0682(13) -.0003(9) .0204(12) -.0007(9) C6 .0368(13) .0192(10) .0476(14) .0008(10) .0044(12) -.0035(10) N6 .0520(14) .0206(10) .0710(16) .0028(10) .0218(13) -.0004(11) N2 .0423(12) .0191(9) .0548(13) .0016(10) .0082(11) -.0002(9) C21 .0382(14) .0203(11) .0624(16) .0023(11) .0012(14) -.0043(11) C211 .0473(15) .0209(11) .0463(14) -.0013(11) .0050(13) .0001(11) O21 .0687(16) .0241(10) .123(2) -.0032(10) .0363(16) -.0137(12) O22 .0484(12) .0326(11) .0794(17) -.0066(9) .0005(12) -.0157(11) C22 .061(2) .070(3) .104(3) .007(2) -.031(2) -.016(2) C23A .053(3) .128(6) .074(4) -.006(4) -.007(3) .037(4) C24A .064(4) .198(11) .140(7) .047(6) -.017(5) -.042(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C2 1.313(3) no N1 C6 1.345(3) no C2 N2 1.337(3) no C2 N3 1.374(3) no N3 C4 1.404(3) no N3 C3 1.470(4) no C4 O4 1.219(3) no C4 C5 1.453(4) no C5 N5 1.329(3) no C5 C6 1.450(3) no N5 O5 1.293(3) no C6 N6 1.303(4) no N2 C21 1.460(3) no C21 C211 1.519(4) no C21 C22 1.528(5) no C211 O22 1.199(4) no C211 O21 1.296(3) no C22 C23A 1.454(4) no C22 C24A 1.466(4) no C22 C24B 1.491(5) no C22 C23B 1.496(5) 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 C2 N1 C6 119.1(2) no N1 C2 N2 117.4(2) no N1 C2 N3 124.9(2) no N2 C2 N3 117.7(2) no C2 N3 C4 120.3(2) no C2 N3 C3 120.9(2) no C4 N3 C3 118.8(2) no O4 C4 N3 120.3(3) no O4 C4 C5 124.4(2) no N3 C4 C5 115.3(2) no N5 C5 C6 126.4(3) no N5 C5 C4 114.7(2) no C6 C5 C4 118.9(2) no O5 N5 C5 116.6(2) no N6 C6 N1 117.2(2) no N6 C6 C5 122.3(2) no N1 C6 C5 120.5(2) no C2 N2 C21 121.7(2) no N2 C21 C211 107.5(2) no N2 C21 C22 111.9(3) no C211 C21 C22 113.6(3) no O22 C211 O21 125.2(3) no O22 C211 C21 122.6(3) no O21 C211 C21 112.2(2) no C23A C22 C24A 113.2(5) no C23A C22 C24B 115.7(5) no C24A C22 C24B 75.9(6) no C23A C22 C23B 73.8(8) no C24A C22 C23B 114.0(6) no C24B C22 C23B 48.3(7) no C23A C22 C21 116.0(4) no C24A C22 C21 115.6(4) no C24B C22 C21 114.3(5) no C23B C22 C21 117.6(7) 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 -178.3(3) no C6 N1 C2 N3 2.6(4) no N1 C2 N3 C4 -9.4(4) no N2 C2 N3 C4 171.5(3) no N1 C2 N3 C3 168.8(3) no N2 C2 N3 C3 -10.2(4) no C2 N3 C4 O4 -174.7(2) no C3 N3 C4 O4 7.0(4) no C2 N3 C4 C5 6.0(4) no C3 N3 C4 C5 -172.3(2) no O4 C4 C5 N5 6.6(4) no N3 C4 C5 N5 -174.2(3) no O4 C4 C5 C6 -176.5(3) no N3 C4 C5 C6 2.8(4) no C6 C5 N5 O5 5.6(5) no C4 C5 N5 O5 -177.7(2) no C2 N1 C6 N6 -176.8(3) no C2 N1 C6 C5 6.8(4) no N5 C5 C6 N6 -9.0(5) no C4 C5 C6 N6 174.4(3) no N5 C5 C6 N1 167.1(3) no C4 C5 C6 N1 -9.4(4) no N1 C2 N2 C21 1.4(4) no N3 C2 N2 C21 -179.5(2) no C2 N2 C21 C211 -140.1(3) no C2 N2 C21 C22 94.5(3) no N2 C21 C211 O22 -3.3(4) no C22 C21 C211 O22 121.1(3) no N2 C21 C211 O21 176.7(3) no C22 C21 C211 O21 -58.9(4) no N2 C21 C22 C23A 67.4(5) no C211 C21 C22 C23A -54.6(5) no N2 C21 C22 C24A -156.5(5) no C211 C21 C22 C24A 81.4(6) no N2 C21 C22 C24B -71.2(6) no C211 C21 C22 C24B 166.8(6) no N2 C21 C22 C23B -17.2(9) no C211 C21 C22 C23B -139.2(8) 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 O4 4_545 .86 2.35 3.146(3) 154 yes N6 H6A O22 3_555 .86 2.06 2.915(3) 172 yes N6 H6B O5 . .86 2.00 2.609(3) 127 yes O21 H21 O5 1_545 .86 1.65 2.483(3) 163 yes O21 H21 N5 1_545 .86 2.46 3.297(3) 166 no C3 H3A O4 . .96 2.31 2.743(3) 107 no C21 H21A N1 . .98 2.31 2.708(2) 104 no _cod_database_code 2102146