#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/88/2008896.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_2008896 loop_ _publ_author_name 'Gambardella, Maria Teresa do Prado' 'Dias, Ricardo Luis Araujo' 'Chehade, Claire Camargos' 'Berlinck, Roberto Gomes de Sousa' _publ_section_title ; 1,3-Dimethylisoguanine trihydrate ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1585 _journal_page_last 1587 _journal_paper_doi 10.1107/S010827019900640X _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C7 H9 N5 O1 , 3H2 O' _chemical_formula_sum 'C7 H15 N5 O4' _chemical_formula_weight 233.24 _chemical_name_systematic ; 1,3-dimethylisoguanine ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 94.580(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.3960(10) _cell_length_b 6.742(2) _cell_length_c 14.1420(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 35 _cell_measurement_theta_min 22 _cell_volume 1083.1(3) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf Nonius, 1989)' _computing_data_reduction 'SDP (Fair, 1990)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54180 _diffrn_reflns_av_R_equivalents 0.043 _diffrn_reflns_av_sigmaI/netI 0.032 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 2182 _diffrn_reflns_theta_max 75.02 _diffrn_reflns_theta_min 4.08 _diffrn_standards_decay_% 1.5 _diffrn_standards_interval_time 120 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 1.01 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 496 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.28 _refine_diff_density_min -0.35 _refine_ls_extinction_coef 0.0022(7) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 2083 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.071 _refine_ls_R_factor_gt 0.048 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0908P)^2^+0.2303P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.161 _reflns_number_gt 1448 _reflns_number_total 2083 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fr1180.cif _cod_data_source_block global _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'none' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0908P)^2^+0.2303P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0908P)^2^+0.2303P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2008896 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 O11 0.14959(15) 0.1473(2) 0.02293(11) 0.0525(5) Uani d . 1 . . O N1 0.11182(15) 0.1433(2) 0.17944(12) 0.0371(4) Uani d . 1 . . N N3 0.30662(15) 0.1420(2) 0.13201(12) 0.0369(4) Uani d . 1 . . N N7 0.33509(16) 0.1459(2) 0.38370(12) 0.0379(4) Uani d . 1 . . N N9 0.45814(15) 0.1430(2) 0.26281(12) 0.0377(4) Uani d . 1 . . N N13 0.07072(17) 0.1418(3) 0.33896(14) 0.0424(5) Uani d . 1 . . N H131 0.100(2) 0.140(3) 0.395(2) 0.051 Uiso d . 1 . . H H132 -0.003(3) 0.142(4) 0.3254(19) 0.051 Uiso d . 1 . . H C2 0.18779(19) 0.1445(3) 0.10562(14) 0.0378(5) Uani d . 1 . . C C4 0.34637(17) 0.1425(3) 0.22620(13) 0.0322(4) Uani d . 1 . . C C5 0.26997(17) 0.1434(3) 0.29691(13) 0.0333(4) Uani d . 1 . . C C6 0.14855(18) 0.1425(3) 0.27417(14) 0.0340(4) Uani d . 1 . . C C8 0.44453(19) 0.1458(3) 0.35833(15) 0.0394(5) Uani d . 1 . . C H81 0.514(2) 0.144(3) 0.4094(18) 0.047 Uiso d . 1 . . H C10 -0.01513(19) 0.1407(3) 0.14951(18) 0.0487(6) Uani d . 1 . . C H101 -0.0260 0.1331 0.0816 0.073 Uiso calc R 1 . . H H102 -0.0510 0.2598 0.1707 0.073 Uiso calc R 1 . . H H103 -0.0510 0.0276 0.1767 0.073 Uiso calc R 1 . . H C12 0.3890(2) 0.1386(4) 0.05833(15) 0.0488(6) Uani d . 1 . . C H121 0.3471 0.1114 -0.0019 0.073 Uiso calc R 1 . . H H122 0.4469 0.0372 0.0725 0.073 Uiso calc R 1 . . H H123 0.4274 0.2651 0.0559 0.073 Uiso calc R 1 . . H OW1 0.19571(17) 0.1305(3) 0.53462(13) 0.0562(5) Uani d . 1 . . O H11 0.260(2) 0.140(4) 0.501(2) 0.067 Uiso d . 1 . . H H12 0.193(3) 0.207(4) 0.5866(18) 0.067 Uiso d . 1 . . H OW2 -0.17967(15) 0.1745(3) 0.33437(12) 0.0523(5) Uani d . 1 . . O H21 -0.220(2) 0.156(4) 0.2904(18) 0.063 Uiso d . 1 . . H H22 -0.200(3) 0.107(4) 0.3837(18) 0.063 Uiso d . 1 . . H OW3 0.67088(15) 0.0881(3) 0.17848(12) 0.0501(4) Uani d . 1 . . O H31 0.603(2) 0.119(4) 0.204(2) 0.060 Uiso d . 1 . . H H32 0.679(2) -0.039(4) 0.1642(19) 0.060 Uiso d . 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 O11 0.0567(10) 0.0669(11) 0.0321(8) 0.0012(8) -0.0076(7) -0.0016(7) N1 0.0374(9) 0.0374(9) 0.0355(9) 0.0009(7) -0.0033(7) -0.0022(7) N3 0.0411(9) 0.0412(9) 0.0284(8) 0.0017(7) 0.0031(7) -0.0002(6) N7 0.0424(9) 0.0401(9) 0.0307(9) 0.0006(7) -0.0001(7) -0.0014(6) N9 0.0370(9) 0.0413(9) 0.0347(9) 0.0006(7) 0.0011(7) -0.0025(7) N13 0.0366(9) 0.0522(11) 0.0383(10) 0.0004(8) 0.0026(8) -0.0014(8) C2 0.0458(11) 0.0345(10) 0.0322(10) 0.0005(8) -0.0024(8) -0.0018(8) C4 0.0389(10) 0.0283(9) 0.0291(9) 0.0004(7) 0.0007(8) -0.0012(7) C5 0.0395(10) 0.0321(9) 0.0281(10) 0.0012(8) 0.0019(8) -0.0009(7) C6 0.0402(10) 0.0288(9) 0.0331(10) 0.0006(7) 0.0029(8) -0.0018(7) C8 0.0405(10) 0.0425(11) 0.0344(10) -0.0001(9) -0.0022(9) -0.0010(8) C10 0.0381(11) 0.0570(14) 0.0493(13) 0.0013(10) -0.0078(9) -0.0065(10) C12 0.0524(13) 0.0624(15) 0.0324(11) 0.0027(11) 0.0083(9) 0.0016(9) OW1 0.0652(11) 0.0637(11) 0.0415(9) -0.0015(9) 0.0144(8) -0.0045(8) OW2 0.0483(9) 0.0679(11) 0.0402(9) -0.0065(8) 0.0005(7) 0.0010(8) OW3 0.0456(9) 0.0570(10) 0.0483(10) 0.0004(8) 0.0061(7) -0.0033(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0181 0.0091 '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_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 4 -1 -6 -1 0 -7 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 124.50(17) yes C6 N1 C10 119.76(18) yes C2 N1 C10 115.74(17) yes C4 N3 C2 120.32(17) yes C4 N3 C12 120.82(18) yes C2 N3 C12 118.86(17) yes C8 N7 C5 102.11(17) no C4 N9 C8 101.68(17) no C6 N13 H131 114.9(19) no C6 N13 H132 123.4(19) no H131 N13 H132 122(3) no O11 C2 N3 122.0(2) no O11 C2 N1 121.29(19) no N3 C2 N1 116.67(17) no N9 C4 N3 127.36(19) no N9 C4 C5 110.91(17) no N3 C4 C5 121.73(18) no C4 C5 N7 108.59(17) no C4 C5 C6 120.35(17) no N7 C5 C6 131.05(18) no N13 C6 N1 120.43(19) yes N13 C6 C5 123.15(19) yes N1 C6 C5 116.42(18) yes N7 C8 N9 116.70(18) no N7 C8 H81 119.7(14) no N9 C8 H81 123.5(14) no N1 C10 H101 109.5 no N1 C10 H102 109.5 no H101 C10 H102 109.5 no N1 C10 H103 109.5 no H101 C10 H103 109.5 no H102 C10 H103 109.5 no N3 C12 H121 109.5 no N3 C12 H122 109.5 no H121 C12 H122 109.5 no N3 C12 H123 109.5 no H121 C12 H123 109.5 no H122 C12 H123 109.5 no H11 OW1 H12 118(3) no H21 OW2 H22 113(3) no H31 OW3 H32 114(2) no 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 O11 C2 . 1.215(2) no N1 C6 . 1.371(3) yes N1 C2 . 1.408(3) yes N1 C10 . 1.475(3) yes N3 C4 . 1.372(2) yes N3 C2 . 1.376(3) yes N3 C12 . 1.458(3) no N7 C8 . 1.325(3) yes N7 C5 . 1.383(2) yes N9 C4 . 1.336(3) yes N9 C8 . 1.372(3) yes N13 C6 . 1.325(3) no N13 H131 . 0.83(3) no N13 H132 . 0.85(3) no C4 C5 . 1.377(3) yes C5 C6 . 1.395(3) yes C8 H81 . 1.03(3) no C10 H101 . 0.9600 no C10 H102 . 0.9600 no C10 H103 . 0.9600 no C12 H121 . 0.9600 no C12 H122 . 0.9600 no C12 H123 . 0.9600 no OW1 H11 . 0.91(2) no OW1 H12 . 0.90(2) no OW2 H21 . 0.76(2) no OW2 H22 . 0.88(2) no OW3 H31 . 0.90(2) no OW3 H32 . 0.89(2) 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 N13 H131 OW1 . 0.83(3) 2.18(3) 3.010(3) 173(2) yes N13 H132 OW2 . 0.85(3) 2.04(3) 2.857(3) 162(2) yes OW1 H11 N7 . 0.91(2) 1.93(3) 2.762(3) 152(3) yes OW1 H12 OW3 4_566 0.90(2) 1.93(2) 2.812(3) 167(3) yes OW2 H21 OW3 1_455 0.76(2) 1.98(2) 2.739(2) 176(3) yes OW2 H22 OW1 3_556 0.88(2) 1.98(2) 2.784(3) 153(3) yes OW3 H31 N9 . 0.90(2) 1.91(2) 2.810(3) 171(2) yes OW3 H32 OW2 2_545 0.89(2) 1.93(2) 2.796(3) 165(2) yes 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 C4 N3 C2 O11 178.83(18) no C12 N3 C2 O11 -1.2(3) no C4 N3 C2 N1 -1.3(3) no C12 N3 C2 N1 178.65(17) no C6 N1 C2 O11 -179.22(19) no C10 N1 C2 O11 1.4(3) no C6 N1 C2 N3 0.9(3) no C10 N1 C2 N3 -178.45(17) no C8 N9 C4 N3 179.32(18) no C8 N9 C4 C5 -0.4(2) no C2 N3 C4 N9 -179.01(18) no C12 N3 C4 N9 1.0(3) no C2 N3 C4 C5 0.7(3) no C12 N3 C4 C5 -179.27(18) no N9 C4 C5 N7 0.4(2) no N3 C4 C5 N7 -179.38(17) no N9 C4 C5 C6 -179.81(17) no N3 C4 C5 C6 0.4(3) no C8 N7 C5 C4 -0.2(2) no C8 N7 C5 C6 -179.9(2) no C2 N1 C6 N13 179.84(18) no C10 N1 C6 N13 -0.8(3) no C2 N1 C6 C5 0.1(3) no C10 N1 C6 C5 179.49(17) no C4 C5 C6 N13 179.48(18) no N7 C5 C6 N13 -0.8(3) no C4 C5 C6 N1 -0.8(3) no N7 C5 C6 N1 178.94(18) no C5 N7 C8 N9 -0.1(2) no C4 N9 C8 N7 0.4(2) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 136188308