#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/52/2205235.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_2205235 loop_ _publ_author_name 'Chernyshev, Ilya V.' 'Tursina, Anna I.' _publ_section_title ; 2-Methyl-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-3-ium chloride, a product of the thermal decomposition of nimustine hydrochloride (ACNU) ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o544 _journal_page_last o546 _journal_paper_doi 10.1107/S1600536805002874 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C7 H9 N4 O +, Cl -' _chemical_formula_moiety 'C7 H9 N4 O +, Cl -' _chemical_formula_sum 'C7 H9 Cl N4 O' _chemical_formula_weight 200.63 _chemical_name_systematic ; 2-Methyl-7-oxo-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-3-ium chloride ; _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 105.60(7) _cell_angle_beta 91.87(7) _cell_angle_gamma 102.17(7) _cell_formula_units_Z 2 _cell_length_a 4.877(3) _cell_length_b 8.104(6) _cell_length_c 11.832(7) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 8.63 _cell_measurement_theta_min 5.28 _cell_volume 438.3(5) _computing_cell_refinement 'CAD-4 EXPRESS' _computing_data_collection 'CAD-4 EXPRESS (Enraf--Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_molecular_graphics ; DIAMOND (Branderburg, 1998) and ORTEP-3 (Farrugia, 1997) ; _computing_publication_material ; WinGX (Farrugia, 1999) ; _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Enraf--Nonius CAD-4' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0978 _diffrn_reflns_av_sigmaI/netI 0.1374 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 1639 _diffrn_reflns_theta_full 19.97 _diffrn_reflns_theta_max 19.97 _diffrn_reflns_theta_min 1.80 _diffrn_standards_decay_% 2 _diffrn_standards_interval_time 120 _diffrn_standards_number 1 _exptl_absorpt_coefficient_mu 0.399 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 208 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.241 _refine_diff_density_min -0.198 _refine_ls_extinction_coef 0.0040(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 120 _refine_ls_number_reflns 821 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.969 _refine_ls_R_factor_all 0.1478 _refine_ls_R_factor_gt 0.0376 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0243P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0662 _refine_ls_wR_factor_ref 0.0863 _reflns_number_gt 421 _reflns_number_total 821 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci6518.cif _cod_data_source_block II _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 2205235 _cod_database_fobs_code 2205235 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 Cl 0.4633(4) 0.6821(2) 0.39839(15) 0.0554(7) Uani d . 1 Cl O1 0.5386(9) -0.1181(5) 0.1028(4) 0.0493(14) Uani d . 1 O N1 0.2644(12) 0.0843(7) 0.1167(4) 0.0413(15) Uani d . 1 N H1 0.3018 0.0920 0.0475 0.050 Uiso calc R 1 H N3 0.3026(11) -0.0475(6) 0.2658(5) 0.0509(16) Uani d . 1 N H3 0.3863 -0.1102 0.2969 0.061 Uiso calc R 1 H N6 -0.1909(11) 0.4086(7) 0.2915(5) 0.0454(15) Uani d . 1 N H6 -0.2867 0.4809 0.3278 0.055 Uiso calc R 1 H N8 0.0333(12) 0.3059(7) 0.1247(4) 0.0448(16) Uani d . 1 N C2 0.3741(15) -0.0368(10) 0.1595(7) 0.0454(19) Uani d . 1 C C4 0.1017(15) 0.0335(9) 0.3350(6) 0.052(2) Uani d . 1 C H4A 0.1803 0.0830 0.4165 0.062 Uiso calc R 1 H H4B -0.0687 -0.0550 0.3324 0.062 Uiso calc R 1 H C5 -0.1187(14) 0.2930(9) 0.3446(6) 0.0460(19) Uani d . 1 C H5 -0.1713 0.2932 0.4195 0.055 Uiso calc R 1 H C7 -0.1173(13) 0.4137(8) 0.1839(6) 0.0393(19) Uani d . 1 C C9 0.1028(14) 0.1908(9) 0.1770(6) 0.0373(18) Uani d . 1 C C10 0.0306(13) 0.1768(8) 0.2882(6) 0.0395(19) Uani d . 1 C C11 -0.2161(15) 0.5387(8) 0.1295(6) 0.060(2) Uani d . 1 C H11A -0.3120 0.4759 0.0530 0.090 Uiso calc R 1 H H11B -0.0573 0.6266 0.1219 0.090 Uiso calc R 1 H H11C -0.3429 0.5943 0.1785 0.090 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 Cl 0.0672(14) 0.0606(13) 0.0491(12) 0.0273(11) 0.0235(9) 0.0213(9) O1 0.060(3) 0.060(3) 0.038(3) 0.032(3) 0.020(3) 0.014(3) N1 0.060(4) 0.049(4) 0.023(3) 0.021(3) 0.014(3) 0.016(3) N3 0.063(4) 0.063(4) 0.041(4) 0.030(3) 0.025(3) 0.024(3) N6 0.052(4) 0.047(4) 0.041(4) 0.025(3) 0.021(3) 0.006(3) N8 0.061(4) 0.042(3) 0.041(4) 0.026(3) 0.013(3) 0.017(3) C2 0.049(5) 0.055(5) 0.035(5) 0.009(4) 0.009(4) 0.019(4) C4 0.059(6) 0.060(5) 0.047(5) 0.022(5) 0.018(4) 0.024(4) C5 0.040(5) 0.055(5) 0.046(5) 0.002(4) 0.007(4) 0.027(5) C7 0.042(5) 0.039(5) 0.043(6) 0.014(4) 0.011(4) 0.017(4) C9 0.033(5) 0.039(4) 0.036(5) 0.015(4) 0.021(4) -0.003(4) C10 0.034(5) 0.052(5) 0.032(5) 0.012(4) 0.015(4) 0.009(4) C11 0.074(6) 0.062(5) 0.058(5) 0.030(5) 0.021(4) 0.028(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' Cl Cl 0.1484 0.1585 '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' H H 0.0000 0.0000 '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 C9 N1 C2 124.8(6) yes C9 N1 H1 117.6 ? C2 N1 H1 117.6 ? C2 N3 C4 128.1(6) y C2 N3 H3 116.0 ? C4 N3 H3 116.0 ? C7 N6 C5 122.0(5) y C7 N6 H6 119.0 ? C5 N6 H6 119.0 ? C7 N8 C9 116.7(5) y O1 C2 N3 124.2(7) y O1 C2 N1 120.5(7) ? N3 C2 N1 115.2(6) y N3 C4 C10 110.6(5) yes N3 C4 H4A 109.5 ? C10 C4 H4A 109.5 ? N3 C4 H4B 109.5 ? C10 C4 H4B 109.5 ? H4A C4 H4B 108.1 ? N6 C5 C10 119.8(6) ? N6 C5 H5 120.1 ? C10 C5 H5 120.1 ? N8 C7 N6 121.2(6) ? N8 C7 C11 120.1(6) ? N6 C7 C11 118.7(6) ? N8 C9 N1 116.0(6) y N8 C9 C10 125.2(6) y N1 C9 C10 118.8(7) ? C5 C10 C9 115.1(6) y C5 C10 C4 124.1(7) y C9 C10 C4 120.8(6) ? C7 C11 H11A 109.5 ? C7 C11 H11B 109.5 ? H11A C11 H11B 109.5 ? C7 C11 H11C 109.5 ? H11A C11 H11C 109.5 ? H11B C11 H11C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 1.244(7) yes N1 C9 1.367(7) yes N1 C2 1.406(7) yes N1 H1 0.86 ? N3 C2 1.336(7) yes N3 C4 1.448(7) yes N3 H3 0.86 ? N6 C7 1.343(7) yes N6 C5 1.356(7) yes N6 H6 0.86 ? N8 C7 1.329(7) yes N8 C9 1.341(8) yes C4 C10 1.510(8) y C4 H4A 0.97 ? C4 H4B 0.97 ? C5 C10 1.359(8) y C5 H5 0.93 ? C7 C11 1.487(7) y C9 C10 1.400(8) y C11 H11A 0.96 ? C11 H11B 0.96 ? C11 H11C 0.96 ? 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 N1 H1 O1 2_655 0.86 2.01 2.859(6) 170 N3 H3 Cl 1_545 0.86 2.40 3.221(6) 161 N6 H6 Cl 1_455 0.86 2.24 3.092(6) 172 C5 H5 Cl 2_566 0.93 2.61 3.501(7) 161 loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21129889 2 PubChem 139067491