#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/15/2011585.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_2011585 loop_ _publ_author_name 'Maulik, Prakas R.' 'Avasthi, Kamlakar' 'Sarkhel, Sanjay' 'Chandra, Tilak' 'Rawat, Diwan S.' 'Logsdon, Brad' 'Jacobson, Robert A.' _publ_section_title ; Disappearance of intramolecular stacking due to one-atom movement or increment of a `propylene linker' in pyrazolo[3,4-d]pyrimidine-based flexible models ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1361 _journal_page_last 1363 _journal_paper_doi 10.1107/S0108270100010775 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C18 H22 N8 O2 S2' _chemical_formula_weight 446.56 _chemical_melting_point 150 _chemical_name_common Pyrazolo[3,4-d]pyrimidine _chemical_name_systematic ; 1-[4-(4-methoxy-6-methylthio-1H-pyrazolo[3,4-d]pyrimidin-1-yl)butyl]- 5-methyl-6-methylthio-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-4-one ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _cell_angle_alpha 90.00 _cell_angle_beta 115.12(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 31.736(7) _cell_length_b 8.308(2) _cell_length_c 17.467(4) _cell_measurement_reflns_used 39 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 12.8 _cell_measurement_theta_min 4.9 _cell_volume 4169.8(18) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1992)' _computing_data_reduction XSCANS _computing_molecular_graphics 'NRCVAX (Gabe et al., 1989)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device_type 'Siemens P4 diffractometer' _diffrn_measurement_method \w-scan _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0000 _diffrn_reflns_av_sigmaI/netI .0324 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 3616 _diffrn_reflns_theta_full 25.01 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_min 2.35 _diffrn_standards_decay_% nil _diffrn_standards_interval_count 97 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .289 _exptl_absorpt_correction_T_max .835 _exptl_absorpt_correction_T_min .772 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(local program; Karcher, 1981)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_meas ? _exptl_crystal_description Trapezoidal _exptl_crystal_F_000 1872 _exptl_crystal_size_max .8 _exptl_crystal_size_mid .6 _exptl_crystal_size_min .5 _refine_diff_density_max .282 _refine_diff_density_min -.221 _refine_ls_extinction_coef .0068(5) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 276 _refine_ls_number_reflns 3616 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.054 _refine_ls_R_factor_all .0460 _refine_ls_R_factor_gt .0410 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0685P)^2^+1.3387P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1210 _reflns_number_gt 3189 _reflns_number_total 3616 _reflns_threshold_expression I>2\s(I) _cod_data_source_file vj1110.cif _cod_data_source_block 5 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 'Monoclinic' changed to 'monoclinic' 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 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 ; _cod_original_cell_volume 4169.8(17) _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2011585 _cod_database_fobs_code 2011585 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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 N1 .08564(6) .62969(18) -.28542(10) .0591(4) Uani d . 1 . . N N2 .09756(6) .7441(2) -.32902(11) .0705(4) Uani d . 1 . . N C3 .09214(8) .8831(3) -.29923(14) .0688(5) Uani d . 1 . . C H3 .0979 .9821 -.3177 .083 Uiso calc R 1 . . H C3A .07636(6) .8636(2) -.23533(12) .0568(4) Uani d . 1 . . C C4 .06206(6) .9544(2) -.18356(12) .0549(4) Uani d . 1 . . C O4 .06165(5) 1.11449(15) -.19000(10) .0693(4) Uani d . 1 . . O CO4 .04383(8) 1.2044(3) -.13974(15) .0752(6) Uani d . 1 . . C HO4A .0432 1.3168 -.1528 .113 Uiso calc R 1 . . H HO4B .0635 1.1877 -.0809 .113 Uiso calc R 1 . . H HO4C .0129 1.1686 -.1520 .113 Uiso calc R 1 . . H N5 .04876(5) .88416(17) -.12953(10) .0551(4) Uani d . 1 . . N C6 .04910(6) .7220(2) -.12731(11) .0542(4) Uani d . 1 . . C S6 .03384(2) .62550(6) -.05308(4) .0699(2) Uani d . 1 . . S CS6 .01876(9) .7890(3) -.00360(16) .0864(7) Uani d . 1 . . C HS6A .0093 .7481 .0381 .130 Uiso calc R 1 . . H HS6B -.0064 .8488 -.0454 .130 Uiso calc R 1 . . H HS6C .0452 .8582 .0232 .130 Uiso calc R 1 . . H N7 .05989(5) .62061(18) -.17441(10) .0574(4) Uani d . 1 . . N C7A .07327(6) .6979(2) -.22805(11) .0540(4) Uani d . 1 . . C N1' .21661(5) .19233(19) -.16005(9) .0570(4) Uani d . 1 . . N N2' .22763(6) .0909(2) -.21125(10) .0673(4) Uani d . 1 . . N C3' .22196(7) -.0549(3) -.18828(12) .0678(5) Uani d . 1 . . C H3' .2271 -.1484 -.2124 .081 Uiso calc R 1 . . H C3'A .20724(6) -.0533(2) -.12306(11) .0581(4) Uani d . 1 . . C C4' .19595(7) -.1701(2) -.07508(12) .0619(5) Uani d . 1 . . C O4' .19753(6) -.31573(18) -.07920(11) .0862(5) Uani d . 1 . . O N5' .18098(5) -.09753(18) -.01662(9) .0574(4) Uani d . 1 . . N C5' .17019(9) -.2054(3) .03898(15) .0774(6) Uani d . 1 . . C H5'1 .1785 -.3136 .0318 .116 Uiso calc R 1 . . H H5'2 .1375 -.2002 .0248 .116 Uiso calc R 1 . . H H5'3 .1875 -.1729 .0967 .116 Uiso calc R 1 . . H C6' .17761(6) .0666(2) -.01024(10) .0511(4) Uani d . 1 . . C S6' .154665(17) .13194(6) .06014(3) .06088(19) Uani d . 1 . . S CS6' .15532(8) .3456(3) .04607(14) .0684(5) Uani d . 1 . . C HS6D .1412 .3981 .0784 .103 Uiso calc R 1 . . H HS6E .1382 .3714 -.0127 .103 Uiso calc R 1 . . H HS6F .1869 .3818 .0650 .103 Uiso calc R 1 . . H N7' .18896(5) .17353(18) -.05219(9) .0532(3) Uani d . 1 . . N C7'A .20397(6) .1076(2) -.10772(10) .0519(4) Uani d . 1 . . C C8 .08687(7) .4594(2) -.30225(13) .0657(5) Uani d . 1 . . C H8A .0862 .4455 -.3579 .079 Uiso calc R 1 . . H H8B .0594 .4080 -.3023 .079 Uiso calc R 1 . . H C9 .12961(7) .3788(2) -.23766(12) .0611(5) Uani d . 1 . . C H9A .1258 .2631 -.2446 .073 Uiso calc R 1 . . H H9B .1323 .4052 -.1817 .073 Uiso calc R 1 . . H C10 .17456(6) .4267(2) -.24342(11) .0597(4) Uani d . 1 . . C H10A .1744 .3835 -.2951 .072 Uiso calc R 1 . . H H10B .1761 .5431 -.2459 .072 Uiso calc R 1 . . H C11 .21670(6) .3659(2) -.16919(12) .0587(4) Uani d . 1 . . C H11A .2444 .3975 -.1758 .070 Uiso calc R 1 . . H H11B .2181 .4160 -.1180 .070 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 .0683(9) .0549(9) .0614(9) .0026(7) .0346(7) -.0009(7) N2 .0866(11) .0689(11) .0694(10) .0038(8) .0460(9) .0066(8) C3 .0837(13) .0626(12) .0735(12) .0059(9) .0464(11) .0100(9) C3A .0581(9) .0518(10) .0639(10) .0047(7) .0292(8) .0068(8) C4 .0541(9) .0475(10) .0645(10) .0018(7) .0264(8) .0032(7) O4 .0872(9) .0456(7) .0887(10) .0050(6) .0504(8) .0072(6) CO4 .0965(15) .0497(11) .0857(14) .0093(10) .0446(12) -.0030(10) N5 .0574(8) .0496(8) .0620(9) .0017(6) .0289(7) .0017(6) C6 .0540(9) .0504(10) .0604(10) -.0001(7) .0265(8) .0011(7) S6 .0917(4) .0570(3) .0802(4) .0014(2) .0549(3) .0063(2) CS6 .1172(18) .0799(15) .0858(14) .0203(13) .0658(14) .0088(12) N7 .0645(9) .0490(8) .0650(9) -.0012(6) .0335(7) -.0003(6) C7A .0532(9) .0521(10) .0590(9) .0022(7) .0260(7) .0010(7) N1' .0695(9) .0587(9) .0528(8) .0089(7) .0356(7) -.0018(7) N2' .0825(10) .0721(11) .0604(9) .0118(8) .0429(8) -.0074(8) C3' .0805(12) .0679(13) .0613(10) .0129(10) .0362(9) -.0135(9) C3'A .0671(10) .0550(10) .0530(9) .0097(8) .0262(8) -.0061(8) C4' .0729(11) .0510(11) .0586(10) .0082(8) .0247(9) -.0055(8) O4' .1227(12) .0478(8) .0925(11) .0073(8) .0500(10) -.0075(7) N5' .0693(9) .0488(8) .0548(8) .0050(6) .0271(7) .0030(6) C5' .1006(15) .0556(12) .0846(14) .0015(10) .0477(12) .0127(10) C6' .0571(9) .0493(9) .0467(8) .0044(7) .0217(7) -.0008(7) S6' .0752(3) .0635(3) .0556(3) .0044(2) .0389(2) .00198(19) CS6' .0860(13) .0624(11) .0710(12) .0039(9) .0471(10) -.0100(9) N7' .0690(8) .0486(8) .0491(7) .0064(6) .0318(6) -.0008(6) C7'A .0585(9) .0534(10) .0465(8) .0089(7) .0249(7) -.0019(7) C8 .0713(11) .0605(11) .0701(11) -.0038(9) .0347(9) -.0120(9) C9 .0747(11) .0497(10) .0686(11) .0003(8) .0399(9) .0018(8) C10 .0731(11) .0551(10) .0593(10) .0006(8) .0360(9) .0023(8) C11 .0676(10) .0594(11) .0589(10) -.0026(8) .0364(9) -.0026(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .1246 .1234 '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 C7A N1 N2 111.02(14) C7A N1 C8 127.11(16) N2 N1 C8 121.87(16) C3 N2 N1 106.13(16) N2 C3 C3A 111.33(18) C7A C3A C4 114.96(16) C7A C3A C3 104.37(17) C4 C3A C3 140.60(18) N5 C4 O4 120.37(16) N5 C4 C3A 120.99(16) O4 C4 C3A 118.63(16) C4 O4 CO4 117.27(15) C4 N5 C6 117.44(16) N7 C6 N5 128.38(16) N7 C6 S6 113.22(13) N5 C6 S6 118.40(13) C6 S6 CS6 103.00(10) C6 N7 C7A 111.83(15) N7 C7A N1 126.56(16) N7 C7A C3A 126.31(17) N1 C7A C3A 107.13(15) C7'A N1' N2' 110.64(15) C7'A N1' C11 127.69(14) N2' N1' C11 121.56(15) C3' N2' N1' 105.11(15) N2' C3' C3'A 112.04(17) C7'A C3'A C3' 104.26(18) C7'A C3'A C4' 119.27(16) C3' C3'A C4' 136.47(18) O4' C4' C3'A 128.11(19) O4' C4' N5' 119.82(19) C3'A C4' N5' 112.07(16) C6' N5' C4' 122.45(16) C6' N5' C5' 120.29(16) C4' N5' C5' 117.24(16) N7' C6' N5' 125.72(15) N7' C6' S6' 118.69(13) N5' C6' S6' 115.58(13) C6' S6' CS6' 100.22(9) C6' N7' C7'A 113.03(15) N1' C7'A N7' 124.65(16) N1' C7'A C3'A 107.94(15) N7' C7'A C3'A 127.37(17) N1 C8 C9 112.09(16) C8 C9 C10 113.92(16) C11 C10 C9 111.76(15) N1' C11 C10 112.76(15) 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 C7A . 1.347(2) ? N1 N2 . 1.368(2) ? N1 C8 . 1.449(2) ? N2 C3 . 1.307(3) ? C3 C3A . 1.413(3) ? C3A C7A . 1.390(3) ? C3A C4 . 1.393(3) ? C4 N5 . 1.322(2) ? C4 O4 . 1.334(2) ? O4 CO4 . 1.439(2) ? N5 C6 . 1.348(2) ? C6 N7 . 1.320(2) ? C6 S6 . 1.7582(18) ? S6 CS6 . 1.781(2) ? N7 C7A . 1.345(2) ? N1' C7'A . 1.343(2) ? N1' N2' . 1.378(2) ? N1' C11 . 1.451(2) ? N2' C3' . 1.313(3) ? C3' C3'A . 1.403(3) ? C3'A C7'A . 1.375(3) ? C3'A C4' . 1.424(3) ? C4' O4' . 1.214(3) ? C4' N5' . 1.430(2) ? N5' C6' . 1.376(2) ? N5' C5' . 1.465(3) ? C6' N7' . 1.296(2) ? C6' S6' . 1.7597(17) ? S6' CS6' . 1.794(2) ? N7' C7'A . 1.364(2) ? C8 C9 . 1.504(3) ? C9 C10 . 1.525(2) ? C10 C11 . 1.501(3) ? 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 C7A N1 N2 C3 -.6(2) C8 N1 N2 C3 179.28(18) N1 N2 C3 C3A -.2(2) N2 C3 C3A C7A .8(2) N2 C3 C3A C4 -175.7(2) C7A C3A C4 N5 2.9(2) C3 C3A C4 N5 179.2(2) C7A C3A C4 O4 -176.53(16) C3 C3A C4 O4 -.3(4) N5 C4 O4 CO4 -3.4(3) C3A C4 O4 CO4 176.02(17) O4 C4 N5 C6 178.70(15) C3A C4 N5 C6 -.7(2) C4 N5 C6 N7 -2.1(3) C4 N5 C6 S6 177.46(12) N7 C6 S6 CS6 -177.38(14) N5 C6 S6 CS6 2.95(17) N5 C6 N7 C7A 2.2(3) S6 C6 N7 C7A -177.39(12) C6 N7 C7A N1 -178.67(16) C6 N7 C7A C3A .5(3) N2 N1 C7A N7 -179.61(16) C8 N1 C7A N7 .5(3) N2 N1 C7A C3A 1.1(2) C8 N1 C7A C3A -178.75(17) C4 C3A C7A N7 -2.9(3) C3 C3A C7A N7 179.58(17) C4 C3A C7A N1 176.40(14) C3 C3A C7A N1 -1.2(2) C7'A N1' N2' C3' -.7(2) C11 N1' N2' C3' -177.18(16) N1' N2' C3' C3'A .2(2) N2' C3' C3'A C7'A .3(2) N2' C3' C3'A C4' 179.9(2) C7'A C3'A C4' O4' -178.8(2) C3' C3'A C4' O4' 1.7(4) C7'A C3'A C4' N5' 1.6(2) C3' C3'A C4' N5' -177.9(2) O4' C4' N5' C6' -178.70(18) C3'A C4' N5' C6' 1.0(2) O4' C4' N5' C5' 2.8(3) C3'A C4' N5' C5' -177.55(16) C4' N5' C6' N7' -3.0(3) C5' N5' C6' N7' 175.49(17) C4' N5' C6' S6' 175.72(13) C5' N5' C6' S6' -5.8(2) N7' C6' S6' CS6' .22(16) N5' C6' S6' CS6' -178.56(14) N5' C6' N7' C7'A 1.9(2) S6' C6' N7' C7'A -176.75(11) N2' N1' C7'A N7' -176.75(15) C11 N1' C7'A N7' -.5(3) N2' N1' C7'A C3'A .9(2) C11 N1' C7'A C3'A 177.14(16) C6' N7' C7'A N1' 178.24(15) C6' N7' C7'A C3'A 1.0(3) C3' C3'A C7'A N1' -.7(2) C4' C3'A C7'A N1' 179.58(15) C3' C3'A C7'A N7' 176.84(17) C4' C3'A C7'A N7' -2.8(3) C7A N1 C8 C9 -78.9(2) N2 N1 C8 C9 101.3(2) N1 C8 C9 C10 -70.2(2) C8 C9 C10 C11 170.26(16) C7'A N1' C11 C10 -99.0(2) N2' N1' C11 C10 76.9(2) C9 C10 C11 N1' 57.8(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21135449 2 PubChem 15399253