#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/31/2013199.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_2013199 loop_ _publ_author_name 'Glidewell, Christopher' 'Low, John N.' 'Melguizo, Manuel' 'Quesada, Antonio' _publ_section_title ; Hydrogen bonding in nitroaniline analogues: hydrogen-bonded sheets in 2-amino-4,6-dimethoxy-5-nitropyrimidine and \p-stacked hydrogen-bonded sheets in 4-amino-2,6-dimethoxy-5-nitropyrimidine ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o14 _journal_page_last o18 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety 'C6 H8 N4 O4' _chemical_formula_sum 'C6 H8 N4 O4' _chemical_formula_weight 200.16 _chemical_name_systematic ; 2-Amino-4,6-dimethoxy-5-nitropyrimidine ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 109.9470(13) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.3443(2) _cell_length_b 7.8437(2) _cell_length_c 14.9129(4) _cell_measurement_reflns_used 1835 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.45 _cell_measurement_theta_min 2.95 _cell_volume 807.54(4) _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, 2002)' _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 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Nonius KappaCCD area-detector' _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 0.062 _diffrn_reflns_av_sigmaI/netI 0.048 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 6065 _diffrn_reflns_theta_full 27.45 _diffrn_reflns_theta_max 27.45 _diffrn_reflns_theta_min 2.95 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_correction_T_min 0.936 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO-SMN; Otwinowski & Minor, 1997)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.646 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 416 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.26 _refine_diff_density_min -0.32 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 129 _refine_ls_number_reflns 1835 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.997 _refine_ls_R_factor_all 0.048 _refine_ls_R_factor_gt 0.040 _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^)+(0.0617P)^2^+0.2772P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.104 _refine_ls_wR_factor_ref 0.110 _reflns_number_gt 1569 _reflns_number_total 1835 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1599.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2013199 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' 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 0.22558(15) 0.10695(13) 0.46351(7) 0.0133(3) Uani d . 1 . . N C2 0.21598(18) 0.02873(16) 0.38128(9) 0.0131(3) Uani d . 1 . . C N2 0.37375(15) -0.04917(15) 0.37713(8) 0.0164(3) Uani d . 1 . . N N3 0.06003(15) 0.02311(14) 0.30037(7) 0.0136(2) Uani d . 1 . . N C4 -0.09743(18) 0.10148(16) 0.30191(9) 0.0127(3) Uani d . 1 . . C O4 -0.25573(13) 0.09551(12) 0.22500(6) 0.0150(2) Uani d . 1 . . O C41 -0.24346(19) -0.00391(18) 0.14537(9) 0.0176(3) Uani d . 1 . . C C5 -0.10622(17) 0.18542(16) 0.38375(9) 0.0130(3) Uani d . 1 . . C N5 -0.27988(15) 0.26800(14) 0.38510(8) 0.0140(3) Uani d . 1 . . N O51 -0.39187(13) 0.32829(12) 0.30986(7) 0.0193(2) Uani d . 1 . . O O52 -0.31205(14) 0.27579(13) 0.46063(7) 0.0206(3) Uani d . 1 . . O C6 0.06565(18) 0.18391(15) 0.46433(9) 0.0127(3) Uani d . 1 . . C O6 0.06585(13) 0.26712(12) 0.54186(6) 0.0164(2) Uani d . 1 . . O C61 0.24604(19) 0.27703(18) 0.62109(9) 0.0172(3) Uani d . 1 . . C H2A 0.4808 -0.0489 0.4271 0.020 Uiso calc R 1 . . H H2B 0.3711 -0.1010 0.3244 0.020 Uiso calc R 1 . . H H41A -0.1467 0.0468 0.1216 0.026 Uiso calc R 1 . . H H41B -0.3699 -0.0047 0.0943 0.026 Uiso calc R 1 . . H H41C -0.2054 -0.1210 0.1664 0.026 Uiso calc R 1 . . H H61A 0.2902 0.1617 0.6435 0.026 Uiso calc R 1 . . H H61B 0.2263 0.3422 0.6731 0.026 Uiso calc R 1 . . H H61C 0.3439 0.3338 0.6005 0.026 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 0.0123(5) 0.0131(5) 0.0131(5) 0.0007(4) 0.0025(4) 0.0004(4) C2 0.0129(6) 0.0120(6) 0.0134(6) -0.0009(4) 0.0030(5) 0.0019(5) N2 0.0123(5) 0.0226(6) 0.0120(5) 0.0035(4) 0.0009(4) -0.0042(4) N3 0.0124(5) 0.0145(5) 0.0125(5) 0.0007(4) 0.0026(4) -0.0003(4) C4 0.0121(6) 0.0114(6) 0.0129(6) -0.0013(4) 0.0020(5) 0.0024(5) O4 0.0121(5) 0.0175(5) 0.0124(5) 0.0012(3) 0.0004(4) -0.0025(4) C41 0.0161(6) 0.0222(7) 0.0130(6) 0.0001(5) 0.0030(5) -0.0039(5) C5 0.0118(6) 0.0118(6) 0.0146(6) 0.0014(4) 0.0035(5) 0.0010(5) N5 0.0134(5) 0.0130(5) 0.0145(5) 0.0000(4) 0.0034(4) -0.0011(4) O51 0.0177(5) 0.0224(5) 0.0153(5) 0.0074(4) 0.0024(4) 0.0047(4) O52 0.0178(5) 0.0303(6) 0.0145(5) 0.0048(4) 0.0065(4) -0.0006(4) C6 0.0142(6) 0.0102(6) 0.0129(6) -0.0009(4) 0.0037(5) 0.0005(5) O6 0.0133(5) 0.0204(5) 0.0129(5) 0.0020(3) 0.0010(4) -0.0051(4) C61 0.0138(6) 0.0215(7) 0.0136(6) -0.0015(5) 0.0014(5) -0.0056(5) 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 . 1.3515(17) y C2 N3 . 1.3515(16) y N3 C4 . 1.3167(16) y C4 C5 . 1.4076(18) y C5 C6 . 1.4151(17) y C6 N1 . 1.3244(16) y C2 N2 . 1.3299(16) y C5 N5 . 1.4367(16) y N5 O51 . 1.2368(14) y N5 O52 . 1.2287(14) y C4 O4 . 1.3265(15) y C6 O6 . 1.3273(15) y N2 H2A . 0.88 no N2 H2B . 0.88 no O4 C41 . 1.4490(15) no C41 H41A . 0.98 no C41 H41B . 0.98 no C41 H41C . 0.98 no O6 C61 . 1.4445(15) no C61 H61A . 0.98 no C61 H61B . 0.98 no C61 H61C . 0.98 no 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 C6 N1 C2 116.32(11) no N2 C2 N1 118.31(11) no N2 C2 N3 115.47(11) no N1 C2 N3 126.22(11) no C2 N2 H2A 120.0 no C2 N2 H2B 120.0 no H2A N2 H2B 120.0 no C4 N3 C2 116.82(11) no N3 C4 O4 118.97(11) no N3 C4 C5 122.26(11) no O4 C4 C5 118.71(11) no C4 O4 C41 116.52(10) no O4 C41 H41A 109.5 no O4 C41 H41B 109.5 no H41A C41 H41B 109.5 no O4 C41 H41C 109.5 no H41A C41 H41C 109.5 no H41B C41 H41C 109.5 no C4 C5 C6 116.16(11) no C4 C5 N5 121.78(11) no C6 C5 N5 122.06(11) no O52 N5 O51 122.44(11) no O52 N5 C5 118.98(11) no O51 N5 C5 118.58(11) no N1 C6 O6 119.65(11) no N1 C6 C5 122.21(11) no O6 C6 C5 118.11(11) no C6 O6 C61 117.87(10) no O6 C61 H61A 109.5 no O6 C61 H61B 109.5 no H61A C61 H61B 109.5 no O6 C61 H61C 109.5 no H61A C61 H61C 109.5 no H61B C61 H61C 109.5 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 H2A N1 3_656 0.88 2.26 3.1210(16) 165 y N2 H2B O51 2_545 0.88 2.13 2.9951(15) 166 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 179.55(11) no C6 N1 C2 N3 0.55(18) no N2 C2 N3 C4 -178.97(11) no N1 C2 N3 C4 0.05(19) no C2 N3 C4 O4 -178.20(11) no C2 N3 C4 C5 -0.96(18) no C5 C4 O4 C41 -175.20(11) no N3 C4 C5 C6 1.20(18) no O4 C4 C5 C6 178.45(11) no N3 C4 C5 N5 -178.90(11) no O4 C4 C5 N5 -1.66(18) no C4 C5 N5 O52 149.85(12) no C6 C5 N5 O52 -30.26(17) no C4 C5 N5 O51 -29.94(17) y C6 C5 N5 O51 149.95(12) y C2 N1 C6 O6 -178.28(11) no C2 N1 C6 C5 -0.25(17) no C4 C5 C6 N1 -0.56(18) no N5 C5 C6 N1 179.55(11) no C4 C5 C6 O6 177.50(11) no N5 C5 C6 O6 -2.40(18) no N1 C6 O6 C61 3.10(17) y N3 C4 O4 C41 2.14(16) y C5 C6 O6 C61 -175.01(11) no _cod_database_fobs_code 2013199