#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2013370.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_2013370 loop_ _publ_author_name 'Arranz Mascar\'os, Paloma' 'Cuesta Martos, Rafael' 'Glidewell, Christopher' 'Low, John N.' _publ_section_title ; Ammonium N-(6-amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)glycinate monohydrate forms hydrogen-bonded bilayers ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o326 _journal_page_last o328 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'N1 H4 1+, C7 H8 N5 O4 1-, H2 O' _chemical_formula_moiety 'N1 H4 1+, C7 H8 N5 O4 1-, H2 O' _chemical_formula_sum 'C7 H14 N6 O5' _chemical_formula_weight 262.24 _chemical_name_systematic ; Ammonium N-(6-amino-3,4-dihydro-3-methyl-5-nitroso-4-oxopyrimidin-2-yl)glycinate monohydrate ; _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 88.4160(10) _cell_angle_beta 78.6950(10) _cell_angle_gamma 70.5270(10) _cell_formula_units_Z 2 _cell_length_a 7.24510(10) _cell_length_b 7.3772(2) _cell_length_c 11.1339(3) _cell_measurement_reflns_used 2508 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.44 _cell_measurement_theta_min 2.93 _cell_volume 549.71(2) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD Server Software (Nonius, 1997)' _computing_data_reduction DENZO-SMN _computing_molecular_graphics 'PLATON (Spek, 2003)' _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 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.043 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 9766 _diffrn_reflns_theta_full 27.44 _diffrn_reflns_theta_max 27.44 _diffrn_reflns_theta_min 2.93 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_correction_T_min 0.967 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO-SMN; Otwinowski & Minor, 1997)' _exptl_crystal_colour pink _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 276 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.390 _refine_diff_density_min -0.418 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 164 _refine_ls_number_reflns 2508 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.000 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0378 _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^)+(0.0683P)^2^+0.3320P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1111 _refine_ls_wR_factor_ref 0.1176 _reflns_number_gt 2328 _reflns_number_total 2508 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1636.cif _[local]_cod_data_source_block I _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 ; _cod_database_code 2013370 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_type_symbol N1 0.17995(16) 0.54573(15) 0.07904(10) 0.0134(2) Uani d . 1 N C2 0.12457(18) 0.41689(18) 0.14928(11) 0.0129(3) Uani d . 1 C N2 0.02742(17) 0.47242(16) 0.26354(10) 0.0156(2) Uani d . 1 N C21 -0.00691(19) 0.66261(18) 0.31595(11) 0.0148(3) Uani d . 1 C C22 -0.13345(18) 0.68649(18) 0.44558(11) 0.0136(3) Uani d . 1 C O21 -0.14059(15) 0.82811(13) 0.50999(9) 0.0190(2) Uani d . 1 O O22 -0.22148(14) 0.56868(13) 0.47891(9) 0.0172(2) Uani d . 1 O N3 0.15741(16) 0.22946(15) 0.11155(10) 0.0142(2) Uani d . 1 N C3 0.0832(2) 0.09854(19) 0.19365(12) 0.0170(3) Uani d . 1 C C4 0.25795(19) 0.16153(18) -0.00748(12) 0.0152(3) Uani d . 1 C O4 0.28110(17) -0.00203(14) -0.04211(10) 0.0248(3) Uani d . 1 O C5 0.32973(19) 0.29652(18) -0.08441(12) 0.0138(3) Uani d . 1 C N5 0.43020(16) 0.22414(16) -0.19680(10) 0.0163(2) Uani d . 1 N O5 0.49779(15) 0.33512(14) -0.27046(9) 0.0198(2) Uani d . 1 O C6 0.28448(18) 0.48943(18) -0.03524(11) 0.0128(3) Uani d . 1 C N6 0.34445(17) 0.61639(16) -0.10237(10) 0.0151(2) Uani d . 1 N O1 0.51577(15) -0.17036(15) -0.30240(9) 0.0213(2) Uani d . 1 O N11 -0.31764(15) 0.23017(15) 0.48612(9) 0.0124(2) Uani d . 1 N H2 -0.0179 0.3913 0.3093 0.019 Uiso calc R 1 H H21A -0.0767 0.7628 0.2639 0.018 Uiso calc R 1 H H21B 0.1226 0.6784 0.3188 0.018 Uiso calc R 1 H H3A 0.1396 0.0850 0.2679 0.026 Uiso calc R 1 H H3B 0.1234 -0.0277 0.1517 0.026 Uiso calc R 1 H H3C -0.0628 0.1512 0.2161 0.026 Uiso calc R 1 H H6A 0.3158 0.7337 -0.0721 0.018 Uiso calc R 1 H H6B 0.4132 0.5840 -0.1776 0.018 Uiso calc R 1 H H1A 0.4787 -0.0615 -0.2598 0.026 Uiso d R 1 H H1B 0.6130 -0.1686 -0.3505 0.026 Uiso d R 1 H H11A -0.2136 0.1047 0.4841 0.015 Uiso d R 1 H H11B -0.3889 0.2224 0.4228 0.015 Uiso d R 1 H H11C -0.4052 0.2625 0.5649 0.015 Uiso d R 1 H H11D -0.2511 0.3264 0.4652 0.015 Uiso d 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 0.0149(5) 0.0124(5) 0.0124(5) -0.0046(4) -0.0014(4) -0.0011(4) C2 0.0123(5) 0.0132(6) 0.0131(6) -0.0038(4) -0.0029(4) -0.0013(4) N2 0.0200(5) 0.0141(5) 0.0127(5) -0.0077(4) 0.0009(4) -0.0015(4) C21 0.0181(6) 0.0142(6) 0.0122(6) -0.0071(5) -0.0002(5) -0.0019(4) C22 0.0140(6) 0.0124(6) 0.0127(6) -0.0025(5) -0.0025(4) 0.0007(4) O21 0.0260(5) 0.0140(5) 0.0152(5) -0.0062(4) -0.0002(4) -0.0040(3) O22 0.0186(5) 0.0167(5) 0.0161(5) -0.0076(4) 0.0003(4) 0.0004(4) N3 0.0175(5) 0.0124(5) 0.0130(5) -0.0062(4) -0.0015(4) 0.0000(4) C3 0.0224(6) 0.0151(6) 0.0150(6) -0.0091(5) -0.0018(5) 0.0014(5) C4 0.0176(6) 0.0128(6) 0.0148(6) -0.0045(5) -0.0025(5) -0.0019(5) O4 0.0381(6) 0.0148(5) 0.0205(5) -0.0118(4) 0.0027(4) -0.0051(4) C5 0.0150(6) 0.0131(6) 0.0130(6) -0.0043(5) -0.0022(5) -0.0018(4) N5 0.0169(5) 0.0171(5) 0.0141(5) -0.0057(4) -0.0009(4) -0.0017(4) O5 0.0234(5) 0.0213(5) 0.0142(5) -0.0101(4) 0.0023(4) -0.0010(4) C6 0.0118(5) 0.0133(6) 0.0128(6) -0.0033(4) -0.0032(4) -0.0004(4) N6 0.0189(5) 0.0124(5) 0.0135(5) -0.0059(4) -0.0004(4) -0.0009(4) O1 0.0218(5) 0.0229(5) 0.0178(5) -0.0088(4) 0.0026(4) -0.0067(4) N11 0.0136(5) 0.0122(5) 0.0111(5) -0.0054(4) 0.0006(4) -0.0025(4) 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 C2 N1 C6 118.34(11) no N1 C2 N2 117.79(11) no N1 C2 N3 124.80(11) no N2 C2 N3 117.41(11) no C2 N2 C21 122.53(11) no C2 N2 H2 118.7 no C21 N2 H2 118.7 no N2 C21 C22 109.84(10) no N2 C21 H21A 109.7 no C22 C21 H21A 109.7 no N2 C21 H21B 109.7 no C22 C21 H21B 109.7 no H21A C21 H21B 108.2 no O22 C22 O21 125.46(12) no O22 C22 C21 118.62(11) no O21 C22 C21 115.92(11) no C2 N3 C4 120.49(11) no C2 N3 C3 121.29(10) no C4 N3 C3 118.19(10) no N3 C3 H3A 109.5 no N3 C3 H3B 109.5 no H3A C3 H3B 109.5 no N3 C3 H3C 109.5 no H3A C3 H3C 109.5 no H3B C3 H3C 109.5 no O4 C4 N3 120.49(12) no O4 C4 C5 123.64(12) no N3 C4 C5 115.87(11) no N5 C5 C6 127.36(12) no N5 C5 C4 114.04(11) no C6 C5 C4 118.59(11) no O5 N5 C5 117.74(11) no N6 C6 N1 117.77(11) no N6 C6 C5 120.45(11) no N1 C6 C5 121.78(11) no C6 N6 H6A 120.0 no C6 N6 H6B 120.0 no H6A N6 H6B 120.0 no H1A O1 H1B 103.5 no H11A N11 H11B 106.0 no H11A N11 H11C 112.1 no H11B N11 H11C 111.6 no H11A N11 H11D 107.6 no H11B N11 H11D 109.3 no H11C N11 H11D 110.2 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C2 1.329(2) y C2 N3 1.385(2) y N3 C4 1.398(2) y C4 C5 1.456(2) y C5 C6 1.447(2) y C6 N1 1.344(2) y C2 N2 1.329(2) y C4 O4 1.224(2) y C5 N5 1.342(2) y N5 O5 1.287(2) y C6 N6 1.315(2) y N2 C21 1.4583(16) no N2 H2 0.88 no C21 C22 1.5304(17) no C21 H21A 0.99 no C21 H21B 0.99 no C22 O22 1.2485(16) no C22 O21 1.2647(16) no N3 C3 1.4704(16) no C3 H3A 0.98 no C3 H3B 0.98 no C3 H3C 0.98 no N6 H6A 0.88 no N6 H6B 0.88 no O1 H1A 0.88 no O1 H1B 0.80 no N11 H11A 0.98 no N11 H11B 0.96 no N11 H11C 0.96 no N11 H11D 0.98 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 O22 . 0.88 2.28 2.655(2) 105 y N6 H6B O5 . 0.88 1.98 2.627(2) 129 y O1 H1A N5 . 0.88 2.13 2.990(2) 165 y O1 H1A O4 . 0.88 2.53 3.113(2) 125 y N11 H11D O22 . 0.98 1.88 2.803(2) 155 y N6 H6A O4 1_565 0.88 1.91 2.776(2) 167 y N6 H6B O1 1_565 0.88 2.47 3.000(2) 119 y O1 H1B O21 1_644 0.80 2.12 2.917(2) 175 y O1 H1B O22 1_644 0.80 2.56 3.043(2) 120 y N11 H11A O21 1_545 0.98 1.96 2.840(2) 149 y N11 H11B O1 2_555 0.96 1.88 2.840(2) 172 y N11 H11C O5 1_456 0.96 1.85 2.782(2) 162 y 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 177.67(11) no C6 N1 C2 N3 -3.57(19) no N1 C2 N2 C21 -4.47(19) y N3 C2 N2 C21 176.68(11) no C2 N2 C21 C22 176.50(11) y N2 C21 C22 O22 -14.22(16) y N2 C21 C22 O21 166.40(11) no N1 C2 N3 C4 1.02(19) no N2 C2 N3 C4 179.78(11) no N1 C2 N3 C3 -177.24(11) no N2 C2 N3 C3 1.52(18) no C2 N3 C4 O4 -177.55(12) no C3 N3 C4 O4 0.76(19) no C2 N3 C4 C5 2.23(18) no C3 N3 C4 C5 -179.46(11) no O4 C4 C5 N5 -2.0(2) y N3 C4 C5 N5 178.25(11) no O4 C4 C5 C6 176.89(13) no N3 C4 C5 C6 -2.88(18) no C6 C5 N5 O5 1.0(2) no C4 C5 N5 O5 179.73(11) no C2 N1 C6 N6 -177.67(11) no C2 N1 C6 C5 2.70(18) no N5 C5 C6 N6 -0.4(2) no C4 C5 C6 N6 -179.13(11) no N5 C5 C6 N1 179.19(12) no C4 C5 C6 N1 0.49(19) no