#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/27/2012758.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_2012758 loop_ _publ_author_name 'Avasthi, Kamlakar' 'Rawat, Diwan S.' 'Chandra, Tilak' 'Sharon, Ashoke' 'Maulik, Prakas R.' _publ_section_title ; Isomeric pyrazolo[3,4-d]pyrimidine-based molecules: disappearance of dimerization due to interchanged substitutions ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o311 _journal_page_last o313 _journal_paper_doi 10.1107/S0108270102006315 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C14 H14 N4 O2' _chemical_formula_moiety 'C14 H14 N4 O2' _chemical_formula_sum 'C14 H14 N4 O2' _chemical_formula_weight 270.29 _chemical_melting_point 165 _chemical_name_common pyrazolo[3,4-d]pyrimidine _chemical_name_systematic ; 5-benzyl-1,7-dimethyl-4,6-dioxo-4,5,6,7-tetrahydropyrazolo[3,4-d]pyrimidine ; _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 _cell_angle_alpha 76.680(10) _cell_angle_beta 89.080(10) _cell_angle_gamma 80.660(10) _cell_formula_units_Z 2 _cell_length_a 7.4760(10) _cell_length_b 8.9230(10) _cell_length_c 10.1550(10) _cell_measurement_reflns_used 59 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 14.89 _cell_measurement_theta_min 5.02 _cell_volume 650.30(13) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_data_reduction XSCANS _computing_molecular_graphics SHELXTL-NT _computing_publication_material SHELXTL-NT _computing_structure_refinement SHELXTL-NT _computing_structure_solution 'SHELXTL-NT (Bruker, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method \q-2\q _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 0.0153 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 3155 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_min 2.06 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 284 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.164 _refine_diff_density_min -0.298 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 183 _refine_ls_number_reflns 2539 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0463 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0745P)^2^+0.1361P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1274 _refine_ls_wR_factor_ref 0.1343 _reflns_number_gt 2128 _reflns_number_total 2539 _reflns_threshold_expression I>2\s(I) _cod_data_source_file gd1201.cif _cod_data_source_block I _cod_original_cell_volume 650.30(10) _cod_database_code 2012758 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 0.02330(18) 0.88518(15) 0.27577(13) 0.0451(3) Uani d . 1 . . N N2 0.14767(19) 0.98266(16) 0.22909(15) 0.0500(4) Uani d . 1 . . N C3 0.2439(2) 0.98326(18) 0.33610(17) 0.0458(4) Uani d . 1 . . C H3 0.3378 1.0404 0.3344 0.055 Uiso calc R 1 . . H C3A 0.18683(19) 0.88677(17) 0.45331(16) 0.0394(3) Uani d . 1 . . C C4 0.2426(2) 0.84822(18) 0.59221(17) 0.0420(4) Uani d . 1 . . C N5 0.14501(17) 0.74149(15) 0.67411(13) 0.0412(3) Uani d . 1 . . N C6 0.0018(2) 0.68083(18) 0.63141(16) 0.0424(4) Uani d . 1 . . C N7 -0.05104(17) 0.72858(14) 0.49623(13) 0.0425(3) Uani d . 1 . . N C7A 0.04519(19) 0.82716(16) 0.40989(15) 0.0381(3) Uani d . 1 . . C C8 0.1934(2) 0.6894(2) 0.81865(16) 0.0472(4) Uani d . 1 . . C H8A 0.0833 0.6883 0.8704 0.057 Uiso calc R 1 . . H H8B 0.2597 0.7636 0.8442 0.057 Uiso calc R 1 . . H C9 0.3071(2) 0.52937(18) 0.85475(15) 0.0414(4) Uani d . 1 . . C C10 0.2802(2) 0.4252(2) 0.97390(17) 0.0529(4) Uani d . 1 . . C H10 0.1897 0.4529 1.0318 0.063 Uiso calc R 1 . . H C11 0.3881(3) 0.2788(2) 1.0076(2) 0.0665(6) Uani d . 1 . . C H11 0.3689 0.2092 1.0880 0.080 Uiso calc R 1 . . H C12 0.5219(3) 0.2363(2) 0.9239(2) 0.0631(5) Uani d . 1 . . C H12 0.5924 0.1377 0.9464 0.076 Uiso calc R 1 . . H C13 0.5515(3) 0.3398(2) 0.8065(2) 0.0616(5) Uani d . 1 . . C H13 0.6436 0.3123 0.7498 0.074 Uiso calc R 1 . . H C14 0.4449(2) 0.4849(2) 0.77241(18) 0.0532(4) Uani d . 1 . . C H14 0.4660 0.5543 0.6924 0.064 Uiso calc R 1 . . H O15 0.36170(17) 0.89873(15) 0.64121(13) 0.0601(4) Uani d . 1 . . O C16 -0.0948(3) 0.8539(3) 0.1761(2) 0.0701(6) Uani d . 1 . . C H16A -0.0809 0.7434 0.1835 0.105 Uiso calc R 1 . . H H16B -0.0629 0.9046 0.0869 0.105 Uiso calc R 1 . . H H16C -0.2186 0.8931 0.1922 0.105 Uiso calc R 1 . . H C17 -0.2185(3) 0.6832(2) 0.4563(2) 0.0634(5) Uani d . 1 . . C H17A -0.3088 0.7746 0.4285 0.095 Uiso calc R 1 . . H H17B -0.2615 0.6128 0.5318 0.095 Uiso calc R 1 . . H H17C -0.1947 0.6326 0.3826 0.095 Uiso calc R 1 . . H O18 -0.07452(17) 0.58907(15) 0.71081(13) 0.0605(4) Uani d . 1 . . O 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 0.0449(7) 0.0438(7) 0.0448(7) -0.0085(6) -0.0043(6) -0.0051(6) N2 0.0491(8) 0.0458(7) 0.0509(8) -0.0100(6) 0.0032(6) -0.0011(6) C3 0.0401(8) 0.0409(8) 0.0549(9) -0.0105(6) 0.0044(7) -0.0056(7) C3A 0.0327(7) 0.0367(7) 0.0485(8) -0.0073(6) 0.0009(6) -0.0084(6) C4 0.0332(7) 0.0412(8) 0.0523(9) -0.0081(6) -0.0018(6) -0.0107(7) N5 0.0374(6) 0.0430(7) 0.0426(7) -0.0088(5) -0.0020(5) -0.0073(5) C6 0.0378(8) 0.0422(8) 0.0476(9) -0.0108(6) 0.0027(6) -0.0079(7) N7 0.0377(7) 0.0422(7) 0.0492(7) -0.0152(5) -0.0030(6) -0.0074(6) C7A 0.0351(7) 0.0331(7) 0.0453(8) -0.0042(6) 0.0000(6) -0.0082(6) C8 0.0467(9) 0.0544(9) 0.0409(8) -0.0086(7) -0.0003(7) -0.0119(7) C9 0.0396(8) 0.0477(8) 0.0391(8) -0.0140(6) -0.0034(6) -0.0092(6) C10 0.0493(9) 0.0656(11) 0.0435(9) -0.0210(8) -0.0018(7) -0.0036(8) C11 0.0752(13) 0.0626(11) 0.0540(11) -0.0254(10) -0.0164(10) 0.0129(9) C12 0.0678(12) 0.0474(10) 0.0698(12) -0.0043(9) -0.0219(10) -0.0065(9) C13 0.0598(11) 0.0586(11) 0.0635(11) 0.0016(9) -0.0015(9) -0.0159(9) C14 0.0568(10) 0.0504(9) 0.0482(9) -0.0062(8) 0.0055(8) -0.0050(7) O15 0.0507(7) 0.0701(8) 0.0639(8) -0.0280(6) -0.0115(6) -0.0110(6) C16 0.0857(14) 0.0780(13) 0.0489(10) -0.0279(11) -0.0174(10) -0.0077(9) C17 0.0544(10) 0.0703(12) 0.0692(12) -0.0340(9) -0.0109(9) -0.0062(9) O18 0.0584(8) 0.0665(8) 0.0564(7) -0.0303(6) 0.0048(6) -0.0002(6) 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 C7A N1 N2 110.53(13) C7A N1 C16 131.66(15) N2 N1 C16 117.62(14) C3 N2 N1 105.63(13) N2 C3 C3A 111.42(14) N2 C3 H3 124.3 C3A C3 H3 124.3 C7A C3A C3 104.76(14) C7A C3A C4 121.32(14) C3 C3A C4 133.90(14) O15 C4 N5 120.59(15) O15 C4 C3A 126.27(15) N5 C4 C3A 113.14(13) C6 N5 C4 125.95(13) C6 N5 C8 115.78(13) C4 N5 C8 118.27(13) O18 C6 N7 121.19(14) O18 C6 N5 120.85(15) N7 C6 N5 117.96(13) C7A N7 C6 118.68(13) C7A N7 C17 123.55(14) C6 N7 C17 117.47(14) N1 C7A N7 129.51(14) N1 C7A C3A 107.65(14) N7 C7A C3A 122.83(14) N5 C8 C9 112.97(13) N5 C8 H8A 109.0 C9 C8 H8A 109.0 N5 C8 H8B 109.0 C9 C8 H8B 109.0 H8A C8 H8B 107.8 C10 C9 C14 118.21(16) C10 C9 C8 120.58(15) C14 C9 C8 121.18(14) C9 C10 C11 120.16(17) C9 C10 H10 119.9 C11 C10 H10 119.9 C12 C11 C10 120.72(17) C12 C11 H11 119.6 C10 C11 H11 119.6 C11 C12 C13 119.51(18) C11 C12 H12 120.2 C13 C12 H12 120.2 C12 C13 C14 120.06(19) C12 C13 H13 120.0 C14 C13 H13 120.0 C13 C14 C9 121.32(17) C13 C14 H14 119.3 C9 C14 H14 119.3 N1 C16 H16A 109.5 N1 C16 H16B 109.5 H16A C16 H16B 109.5 N1 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 N7 C17 H17A 109.5 N7 C17 H17B 109.5 H17A C17 H17B 109.5 N7 C17 H17C 109.5 H17A C17 H17C 109.5 H17B C17 H17C 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 C7A . 1.343(2) ? N1 N2 . 1.380(2) ? N1 C16 . 1.457(2) ? N2 C3 . 1.314(2) ? C3 C3A . 1.404(2) ? C3 H3 . 0.9300 ? C3A C7A . 1.380(2) ? C3A C4 . 1.425(2) ? C4 O15 . 1.2211(19) ? C4 N5 . 1.404(2) ? N5 C6 . 1.392(2) ? N5 C8 . 1.466(2) ? C6 O18 . 1.2161(19) ? C6 N7 . 1.384(2) ? N7 C7A . 1.3747(19) ? N7 C17 . 1.467(2) ? C8 C9 . 1.506(2) ? C8 H8A . 0.9700 ? C8 H8B . 0.9700 ? C9 C10 . 1.380(2) ? C9 C14 . 1.382(2) ? C10 C11 . 1.390(3) ? C10 H10 . 0.9300 ? C11 C12 . 1.366(3) ? C11 H11 . 0.9300 ? C12 C13 . 1.369(3) ? C12 H12 . 0.9300 ? C13 C14 . 1.378(3) ? C13 H13 . 0.9300 ? C14 H14 . 0.9300 ? C16 H16A . 0.9600 ? C16 H16B . 0.9600 ? C16 H16C . 0.9600 ? C17 H17A . 0.9600 ? C17 H17B . 0.9600 ? C17 H17C . 0.9600 ? 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 C3 H3 O15 2_676 0.93 2.42 3.317(2) 161 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 -0.24(17) C16 N1 N2 C3 -175.89(15) N1 N2 C3 C3A 0.50(18) N2 C3 C3A C7A -0.57(18) N2 C3 C3A C4 -179.27(16) C7A C3A C4 O15 -177.37(15) C3 C3A C4 O15 1.2(3) C7A C3A C4 N5 2.6(2) C3 C3A C4 N5 -178.90(16) O15 C4 N5 C6 177.15(14) C3A C4 N5 C6 -2.8(2) O15 C4 N5 C8 -1.7(2) C3A C4 N5 C8 178.34(12) C4 N5 C6 O18 -179.73(14) C8 N5 C6 O18 -0.9(2) C4 N5 C6 N7 0.1(2) C8 N5 C6 N7 178.93(13) O18 C6 N7 C7A -177.18(14) N5 C6 N7 C7A 3.0(2) O18 C6 N7 C17 8.9(2) N5 C6 N7 C17 -170.91(14) N2 N1 C7A N7 178.80(14) C16 N1 C7A N7 -6.4(3) N2 N1 C7A C3A -0.12(17) C16 N1 C7A C3A 174.72(18) C6 N7 C7A N1 177.97(14) C17 N7 C7A N1 -8.5(3) C6 N7 C7A C3A -3.3(2) C17 N7 C7A C3A 170.28(15) C3 C3A C7A N1 0.40(16) C4 C3A C7A N1 179.30(13) C3 C3A C7A N7 -178.60(13) C4 C3A C7A N7 0.3(2) C6 N5 C8 C9 79.46(17) C4 N5 C8 C9 -101.57(16) N5 C8 C9 C10 -141.39(15) N5 C8 C9 C14 41.0(2) C14 C9 C10 C11 -1.1(2) C8 C9 C10 C11 -178.77(15) C9 C10 C11 C12 0.2(3) C10 C11 C12 C13 0.9(3) C11 C12 C13 C14 -1.0(3) C12 C13 C14 C9 0.1(3) C10 C9 C14 C13 0.9(3) C8 C9 C14 C13 178.64(16) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21134848 2 PubChem 15434871