#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/27/2012759.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_2012759 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_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 142 _chemical_name_common pyrazolo[3,4-d]pyrimidine _chemical_name_systematic ; 1-benzyl-5,7-dimethyl-4-dioxo-4,5,6,7-tetrahydropyrazolo[3,4-d]pyrimidine ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 108.940(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 12.4680(10) _cell_length_b 7.4490(10) _cell_length_c 15.076(2) _cell_measurement_reflns_used 43 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 12.5 _cell_measurement_theta_min 5.13 _cell_volume 1324.4(3) _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 0.994 _diffrn_measured_fraction_theta_max 0.994 _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 0.0890 _diffrn_reflns_av_sigmaI/netI 0.0712 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 3782 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 1.85 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 568 _exptl_crystal_size_max 0.375 _exptl_crystal_size_mid 0.275 _exptl_crystal_size_min 0.200 _refine_diff_density_max 0.172 _refine_diff_density_min -0.216 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 183 _refine_ls_number_reflns 2885 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.012 _refine_ls_R_factor_all 0.1301 _refine_ls_R_factor_gt 0.0593 _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^)+(0.0653P)^2^+0.0892P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1301 _refine_ls_wR_factor_ref 0.1588 _reflns_number_gt 1504 _reflns_number_total 2885 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gd1201.cif _[local]_cod_data_source_block II _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_database_code 2012759 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 N1 0.20916(16) 0.9282(3) 0.00658(13) 0.0581(6) Uani d . 1 . . N N2 0.1691(2) 0.9101(3) -0.08991(14) 0.0661(6) Uani d . 1 . . N C3 0.0697(2) 0.8320(4) -0.10896(17) 0.0633(7) Uani d . 1 . . C H3 0.0223 0.8059 -0.1693 0.076 Uiso calc R 1 . . H C3A 0.0439(2) 0.7932(3) -0.02766(15) 0.0511(6) Uani d . 1 . . C C4 -0.0514(2) 0.7118(3) -0.00995(17) 0.0560(6) Uani d . 1 . . C N5 -0.03889(15) 0.7023(3) 0.08547(13) 0.0539(5) Uani d . 1 . . N C6 0.0535(2) 0.7604(3) 0.15857(16) 0.0525(6) Uani d . 1 . . C N7 0.14192(15) 0.8447(3) 0.13688(12) 0.0513(5) Uani d . 1 . . N C7A 0.13447(19) 0.8556(3) 0.04462(15) 0.0493(6) Uani d . 1 . . C C8 0.3228(2) 0.9998(4) 0.04671(19) 0.0663(7) Uani d . 1 . . C H8A 0.3236 1.0818 0.0969 0.080 Uiso calc R 1 . . H H8B 0.3411 1.0686 -0.0011 0.080 Uiso calc R 1 . . H C9 0.4136(2) 0.8603(4) 0.08494(17) 0.0580(6) Uani d . 1 . . C C10 0.3924(2) 0.6790(4) 0.0765(2) 0.0835(9) Uani d . 1 . . C H10 0.3190 0.6383 0.0463 0.100 Uiso calc R 1 . . H C11 0.4787(3) 0.5570(5) 0.1123(3) 0.1017(11) Uani d . 1 . . C H11 0.4634 0.4345 0.1069 0.122 Uiso calc R 1 . . H C12 0.5870(3) 0.6161(7) 0.1558(2) 0.0965(12) Uani d . 1 . . C H12 0.6458 0.5341 0.1787 0.116 Uiso calc R 1 . . H C13 0.6081(3) 0.7957(7) 0.1656(2) 0.0937(11) Uani d . 1 . . C H13 0.6813 0.8364 0.1963 0.112 Uiso calc R 1 . . H C14 0.5226(2) 0.9156(5) 0.13061(19) 0.0771(9) Uani d . 1 . . C H14 0.5383 1.0378 0.1378 0.093 Uiso calc R 1 . . H O15 -0.13713(16) 0.6565(3) -0.06912(12) 0.0795(6) Uani d . 1 . . O C16 -0.1335(2) 0.6290(4) 0.1117(2) 0.0709(8) Uani d . 1 . . C H16A -0.1072 0.5297 0.1537 0.106 Uiso calc R 1 . . H H16B -0.1920 0.5889 0.0564 0.106 Uiso calc R 1 . . H H16C -0.1631 0.7205 0.1421 0.106 Uiso calc R 1 . . H O17 0.05736(15) 0.7429(3) 0.23962(12) 0.0705(6) Uani d . 1 . . O C18 0.2302(2) 0.9323(4) 0.21321(17) 0.0726(8) Uani d . 1 . . C H18A 0.3026 0.8811 0.2183 0.109 Uiso calc R 1 . . H H18B 0.2148 0.9150 0.2710 0.109 Uiso calc R 1 . . H H18C 0.2310 1.0585 0.2004 0.109 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 0.0600(12) 0.0600(13) 0.0538(12) 0.0080(11) 0.0178(10) 0.0070(11) N2 0.0790(15) 0.0691(15) 0.0534(12) 0.0141(13) 0.0260(11) 0.0080(11) C3 0.0744(18) 0.0637(18) 0.0489(14) 0.0156(15) 0.0160(13) -0.0008(13) C3A 0.0534(14) 0.0521(13) 0.0428(12) 0.0139(12) 0.0088(11) 0.0003(11) C4 0.0579(15) 0.0520(15) 0.0519(14) 0.0117(12) 0.0091(12) -0.0065(12) N5 0.0511(11) 0.0527(13) 0.0563(12) 0.0056(10) 0.0152(9) -0.0015(10) C6 0.0595(15) 0.0509(15) 0.0462(13) 0.0128(12) 0.0160(12) 0.0006(11) N7 0.0520(11) 0.0557(12) 0.0419(10) 0.0032(10) 0.0092(9) 0.0012(9) C7A 0.0543(13) 0.0466(13) 0.0468(12) 0.0145(12) 0.0162(11) 0.0064(11) C8 0.0630(16) 0.0637(17) 0.0756(17) -0.0007(14) 0.0275(13) 0.0081(14) C9 0.0565(15) 0.0669(17) 0.0568(14) 0.0002(13) 0.0268(12) 0.0021(13) C10 0.0636(17) 0.072(2) 0.110(2) 0.0072(16) 0.0207(16) 0.0067(18) C11 0.096(3) 0.084(2) 0.130(3) 0.027(2) 0.044(2) 0.021(2) C12 0.079(2) 0.137(4) 0.082(2) 0.047(2) 0.0378(18) 0.021(2) C13 0.0597(19) 0.143(4) 0.078(2) 0.012(2) 0.0226(15) -0.015(2) C14 0.0610(17) 0.094(2) 0.0831(19) -0.0039(17) 0.0327(15) -0.0126(17) O15 0.0662(12) 0.0913(15) 0.0668(12) -0.0064(11) 0.0020(10) -0.0121(11) C16 0.0677(17) 0.0635(17) 0.0863(19) -0.0038(14) 0.0316(15) -0.0029(15) O17 0.0825(12) 0.0779(14) 0.0543(11) -0.0013(10) 0.0265(9) 0.0033(9) C18 0.0718(17) 0.085(2) 0.0521(14) -0.0112(15) 0.0081(13) -0.0018(14) 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 . 1.355(3) ? N1 N2 . 1.383(3) ? N1 C8 . 1.449(3) ? N2 C3 . 1.314(3) ? C3 C3A . 1.395(3) ? C3 H3 . 0.9300 ? C3A C7A . 1.371(3) ? C3A C4 . 1.434(4) ? C4 O15 . 1.220(3) ? C4 N5 . 1.398(3) ? N5 C6 . 1.380(3) ? N5 C16 . 1.465(3) ? C6 O17 . 1.214(3) ? C6 N7 . 1.396(3) ? N7 C7A . 1.366(3) ? N7 C18 . 1.463(3) ? C8 C9 . 1.507(4) ? C8 H8A . 0.9700 ? C8 H8B . 0.9700 ? C9 C14 . 1.373(3) ? C9 C10 . 1.374(4) ? C10 C11 . 1.378(4) ? C10 H10 . 0.9300 ? C11 C12 . 1.368(5) ? C11 H11 . 0.9300 ? C12 C13 . 1.362(5) ? C12 H12 . 0.9300 ? C13 C14 . 1.359(5) ? C13 H13 . 0.9300 ? C14 H14 . 0.9300 ? C16 H16A . 0.9600 ? C16 H16B . 0.9600 ? C16 H16C . 0.9600 ? C18 H18A . 0.9600 ? C18 H18B . 0.9600 ? C18 H18C . 0.9600 ? 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 110.08(19) C7A N1 C8 133.1(2) N2 N1 C8 116.4(2) C3 N2 N1 105.41(19) N2 C3 C3A 111.7(2) N2 C3 H3 124.1 C3A C3 H3 124.1 C7A C3A C3 105.2(2) C7A C3A C4 120.9(2) C3 C3A C4 133.8(2) O15 C4 N5 120.9(2) O15 C4 C3A 126.1(2) N5 C4 C3A 113.0(2) C6 N5 C4 126.2(2) C6 N5 C16 116.0(2) C4 N5 C16 117.8(2) O17 C6 N5 121.3(2) O17 C6 N7 120.5(2) N5 C6 N7 118.2(2) C7A N7 C6 117.86(19) C7A N7 C18 124.0(2) C6 N7 C18 117.76(19) N1 C7A N7 128.7(2) N1 C7A C3A 107.5(2) N7 C7A C3A 123.7(2) N1 C8 C9 114.7(2) N1 C8 H8A 108.6 C9 C8 H8A 108.6 N1 C8 H8B 108.6 C9 C8 H8B 108.6 H8A C8 H8B 107.6 C14 C9 C10 118.1(3) C14 C9 C8 118.9(3) C10 C9 C8 122.9(2) C9 C10 C11 120.6(3) C9 C10 H10 119.7 C11 C10 H10 119.7 C12 C11 C10 120.0(4) C12 C11 H11 120.0 C10 C11 H11 120.0 C13 C12 C11 119.6(3) C13 C12 H12 120.2 C11 C12 H12 120.2 C14 C13 C12 120.2(3) C14 C13 H13 119.9 C12 C13 H13 119.9 C13 C14 C9 121.4(3) C13 C14 H14 119.3 C9 C14 H14 119.3 N5 C16 H16A 109.5 N5 C16 H16B 109.5 H16A C16 H16B 109.5 N5 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 N7 C18 H18A 109.5 N7 C18 H18B 109.5 H18A C18 H18B 109.5 N7 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 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 1.9(3) C8 N1 N2 C3 175.6(2) N1 N2 C3 C3A -1.7(3) N2 C3 C3A C7A 0.9(3) N2 C3 C3A C4 179.6(3) C7A C3A C4 O15 177.9(2) C3 C3A C4 O15 -0.6(5) C7A C3A C4 N5 -1.1(3) C3 C3A C4 N5 -179.6(2) O15 C4 N5 C6 -179.8(2) C3A C4 N5 C6 -0.8(3) O15 C4 N5 C16 -1.8(3) C3A C4 N5 C16 177.2(2) C4 N5 C6 O17 -178.5(2) C16 N5 C6 O17 3.5(3) C4 N5 C6 N7 3.2(3) C16 N5 C6 N7 -174.9(2) O17 C6 N7 C7A 178.1(2) N5 C6 N7 C7A -3.6(3) O17 C6 N7 C18 -8.4(4) N5 C6 N7 C18 170.0(2) N2 N1 C7A N7 179.6(2) C8 N1 C7A N7 7.3(4) N2 N1 C7A C3A -1.3(3) C8 N1 C7A C3A -173.7(2) C6 N7 C7A N1 -179.2(2) C18 N7 C7A N1 7.8(4) C6 N7 C7A C3A 1.9(3) C18 N7 C7A C3A -171.2(2) C3 C3A C7A N1 0.3(3) C4 C3A C7A N1 -178.6(2) C3 C3A C7A N7 179.4(2) C4 C3A C7A N7 0.5(4) C7A N1 C8 C9 73.6(3) N2 N1 C8 C9 -98.4(2) N1 C8 C9 C14 -175.2(2) N1 C8 C9 C10 4.6(4) C14 C9 C10 C11 -0.6(4) C8 C9 C10 C11 179.6(3) C9 C10 C11 C12 -0.7(5) C10 C11 C12 C13 1.7(5) C11 C12 C13 C14 -1.3(5) C12 C13 C14 C9 0.0(5) C10 C9 C14 C13 0.9(4) C8 C9 C14 C13 -179.3(3) _journal_paper_doi 10.1107/S0108270102006315