#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/72/2007236.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_2007236 loop_ _publ_author_name 'Sood, Geeta' 'Schwalbe, Carl H.' 'Fraser, William' _publ_section_title ; 6-Amino-9-(carboxymethyl)-2-methoxypurine Methyl Ester ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 659 _journal_page_last 661 _journal_paper_doi 10.1107/S0108270197015795 _journal_volume 54 _journal_year 1998 _chemical_formula_moiety 'C9 H11 N5 O3' _chemical_formula_sum 'C9 H11 N5 O3' _chemical_formula_weight 237.23 _chemical_melting_point .491E-305 _chemical_name_systematic ; 6-Amino-9-(carboxymethyl)-2-methoxypurine Methyl Ester ; _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 _cell_angle_alpha 90.00 _cell_angle_beta 99.97(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.085(3) _cell_length_b 7.7168(6) _cell_length_c 13.006(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 37.9 _cell_measurement_theta_min 23.5 _cell_volume 1095.7(4) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'CADABS (Gould & Smith, 1986)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'MULTAN84 (Main et al., 1984)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device '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 1.54178 _diffrn_reflns_av_R_equivalents 0.062 _diffrn_reflns_av_sigmaI/netI 0.032 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 2486 _diffrn_reflns_theta_max 66.94 _diffrn_reflns_theta_min 4.85 _diffrn_standards_decay_% 3 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.947 _exptl_absorpt_correction_T_max 0.94 _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_type 'empirical via \y scans (North et al., 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_meas ? _exptl_crystal_description plate _exptl_crystal_F_000 496 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.175 _refine_diff_density_min -0.163 _refine_ls_extinction_coef 0.0071(6) _refine_ls_extinction_method SHELXL93 _refine_ls_goodness_of_fit_all 1.381 _refine_ls_goodness_of_fit_obs 1.408 _refine_ls_hydrogen_treatment 'H atoms treated by a mixture of independent and constrained refinement' _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 1946 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.381 _refine_ls_restrained_S_obs 1.408 _refine_ls_R_factor_all 0.041 _refine_ls_R_factor_obs .038 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0346P)^2^+0.1761P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.101 _refine_ls_wR_factor_obs .100 _reflns_number_observed 1818 _reflns_number_total 1946 _reflns_observed_criterion I>2\s(I) _cod_data_source_file jz1235.cif _cod_data_source_block gsa314 _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' 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^)+(0.0346P)^2^+0.1761P] 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^)+(0.0346P)^2^+0.1761P] where P = (Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1095.8(3) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2007236 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_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 .0450(6) .0468(7) .0441(6) -.0035(5) .0031(5) -.0072(6) C2 .0420(7) .0506(8) .0387(7) .0010(6) .0016(6) -.0066(6) N3 .0445(6) .0480(7) .0394(6) -.0009(5) .0044(5) -.0032(5) C4 .0331(6) .0417(7) .0394(7) .0016(6) .0001(5) -.0036(6) C5 .0347(7) .0447(8) .0383(7) -.0008(6) .0012(5) -.0037(6) C6 .0352(7) .0456(8) .0429(7) -.0023(6) .0009(5) -.0034(6) O2 .0752(7) .0659(8) .0432(6) -.0067(6) .0132(5) -.0145(5) C14 .106(2) .0877(15) .0425(9) -.0111(12) .0220(9) -.0060(9) N6 .0700(9) .0535(8) .0488(7) -.0208(7) .0121(6) -.0084(7) N7 .0493(7) .0521(8) .0403(6) -.0061(6) .0060(5) -.0068(6) C8 .0485(8) .0479(9) .0431(8) -.0044(7) .0062(6) -.0090(7) N9 .0418(6) .0403(7) .0430(6) -.0031(5) .0046(5) -.0045(5) C10 .0464(8) .0388(8) .0496(8) .0009(6) .0050(6) .0019(6) C11 .0473(8) .0368(7) .0439(7) -.0013(6) .0036(6) -.0045(6) O11 .0590(7) .0657(8) .0589(7) .0177(6) .0049(5) .0107(6) O12 .0586(7) .0548(7) .0662(7) .0024(5) .0224(5) .0096(6) C13 .0703(12) .0658(12) .128(2) .0064(10) .0530(12) .0052(13) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol N1 .41329(11) .3074(2) .51456(9) .0458(3) Uani d . 1 . N C2 .36017(13) .1944(2) .57071(11) .0444(4) Uani d . 1 . C N3 .31751(11) .0367(2) .54562(9) .0443(3) Uani d . 1 . N C4 .33382(11) -.0030(2) .44843(10) .0388(3) Uani d . 1 . C C5 .38443(12) .0979(2) .38006(10) .0399(3) Uani d . 1 . C C6 .42672(12) .2629(2) .41703(11) .0419(3) Uani d . 1 . C O2 .34931(11) .2594(2) .66467(8) .0611(3) Uani d . 1 . O C14 .2941(2) .1484(3) .73292(14) .0778(6) Uani d . 1 . C H141 .2849(15) .2112(8) .7948(6) .117 Uiso calc R 1 . H H142 .3455(8) .0493(12) .7518(11) .117 Uiso calc R 1 . H H143 .2151(7) .1108(18) .6976(5) .117 Uiso calc R 1 . H N6 .47857(14) .3764(2) .36119(11) .0572(4) Uani d . 1 . N H61 .4855(18) .351(3) .2959(17) .069 Uiso d . 1 . H H62 .5050(18) .479(3) .3928(16) .069 Uiso d . 1 . H N7 .38478(11) .0096(2) .28659(9) .0475(3) Uani d . 1 . N C8 .33439(13) -.1392(2) .30148(11) .0467(4) Uani d . 1 . C H8 .32173(13) -.2259(2) .25113(11) .056 Uiso calc R 1 . H N9 .30193(10) -.1560(2) .39770(9) .0420(3) Uani d . 1 . N C10 .23725(13) -.2955(2) .43854(12) .0453(4) Uani d . 1 . C H101 .27830(13) -.3245(2) .50844(12) .054 Uiso calc R 1 . H H102 .23785(13) -.3973(2) .39494(12) .054 Uiso calc R 1 . H C11 .10679(13) -.2432(2) .44142(11) .0432(3) Uani d . 1 . C O11 .04791(11) -.1458(2) .38053(9) .0618(3) Uani d . 1 . O O12 .06650(10) -.3199(2) .51959(9) .0585(3) Uani d . 1 . O C13 -.0576(2) -.2803(3) .5324(2) .0837(7) Uani d . 1 . C H131 -.1134(2) -.315(2) .4711(7) .125 Uiso calc R 1 . H H132 -.0653(5) -.1578(4) .5426(14) .125 Uiso calc R 1 . H H133 -.0764(6) -.3412(19) .5920(9) .125 Uiso calc R 1 . H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 118.60(13) ? N3 C2 N1 129.50(13) yes N3 C2 O2 118.79(14) ? N1 C2 O2 111.70(14) ? C2 N3 C4 109.91(12) ? N3 C4 N9 125.79(13) ? N3 C4 C5 128.12(13) ? N9 C4 C5 106.10(12) ? C4 C5 N7 110.56(13) ? C4 C5 C6 116.07(13) ? N7 C5 C6 133.36(13) ? N6 C6 N1 118.38(14) ? N6 C6 C5 123.83(13) ? N1 C6 C5 117.79(13) yes C2 O2 C14 116.82(14) ? O2 C14 H141 109.47(10) ? O2 C14 H142 109.47(12) ? H141 C14 H142 109.5 ? O2 C14 H143 109.47(10) ? H141 C14 H143 109.5 ? H142 C14 H143 109.5 ? C6 N6 H61 119.6(14) ? C6 N6 H62 117.2(12) ? H61 N6 H62 123.2(19) ? C8 N7 C5 103.56(12) ? N7 C8 N9 113.98(13) ? N7 C8 H8 123.01(8) ? N9 C8 H8 123.01(8) ? C4 N9 C8 105.81(12) ? C4 N9 C10 124.66(12) ? C8 N9 C10 129.31(12) ? N9 C10 C11 110.44(12) ? N9 C10 H101 109.56(7) ? C11 C10 H101 109.56(8) ? N9 C10 H102 109.56(8) ? C11 C10 H102 109.56(8) ? H101 C10 H102 108.1 ? O11 C11 O12 124.87(14) ? O11 C11 C10 124.44(14) ? O12 C11 C10 110.69(12) ? C11 O12 C13 116.71(15) ? O12 C13 H131 109.47(12) ? O12 C13 H132 109.47(10) ? H131 C13 H132 109.5 ? O12 C13 H133 109.47(11) ? H131 C13 H133 109.5 ? H132 C13 H133 109.5 ? 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 . 1.338(2) ? N1 C6 . 1.347(2) ? C2 N3 . 1.326(2) ? C2 O2 . 1.346(2) yes N3 C4 . 1.343(2) ? C4 N9 . 1.369(2) ? C4 C5 . 1.373(2) ? C5 N7 . 1.394(2) ? C5 C6 . 1.412(2) ? C6 N6 . 1.330(2) yes O2 C14 . 1.444(2) ? C14 H141 . .96 ? C14 H142 . .96 ? C14 H143 . .96 ? N6 H61 . .89(2) ? N6 H62 . .91(2) ? N7 C8 . 1.306(2) ? C8 N9 . 1.367(2) ? C8 H8 . .93 ? N9 C10 . 1.445(2) ? C10 C11 . 1.508(2) ? C10 H101 . .97 ? C10 H102 . .97 ? C11 O11 . 1.200(2) yes C11 O12 . 1.319(2) ? O12 C13 . 1.446(2) ? C13 H131 . .96 ? C13 H132 . .96 ? C13 H133 . .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 _geom_hbond_publ_flag N6 H61 O11 4_666 0.89(2) 2.26(2) 3.111(2) 160(2) yes N6 H62 N1 3_666 0.91(2) 2.15(2) 3.055(2) 171(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 C6 N1 C2 N3 0.9(2) ? C6 N1 C2 O2 -177.78(12) ? N1 C2 N3 C4 -0.3(2) ? O2 C2 N3 C4 178.38(12) ? C2 N3 C4 N9 179.20(12) ? C2 N3 C4 C5 -0.9(2) ? N3 C4 C5 N7 -179.95(13) ? N9 C4 C5 N7 -0.03(15) ? N3 C4 C5 C6 1.2(2) ? N9 C4 C5 C6 -178.83(11) ? C2 N1 C6 N6 179.40(13) ? C2 N1 C6 C5 -0.5(2) ? C4 C5 C6 N6 179.67(14) ? N7 C5 C6 N6 1.2(2) ? C4 C5 C6 N1 -0.4(2) ? N7 C5 C6 N1 -178.90(14) ? N3 C2 O2 C14 1.7(2) yes N1 C2 O2 C14 -179.48(15) yes C4 C5 N7 C8 0.3(2) ? C6 C5 N7 C8 178.84(15) ? C5 N7 C8 N9 -0.5(2) ? N3 C4 N9 C8 179.66(13) ? C5 C4 N9 C8 -0.26(14) ? N3 C4 N9 C10 4.6(2) ? C5 C4 N9 C10 -175.30(12) ? N7 C8 N9 C4 0.5(2) ? N7 C8 N9 C10 175.23(13) ? C4 N9 C10 C11 69.3(2) ? C8 N9 C10 C11 -104.5(2) yes N9 C10 C11 O11 31.5(2) yes N9 C10 C11 O12 -148.82(13) ? O11 C11 O12 C13 -0.8(2) yes C10 C11 O12 C13 179.46(15) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21137107 2 PubChem 102120491