#------------------------------------------------------------------------------ #$Date: 2015-01-23 12:30:19 +0000 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/15/2011584.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_2011584 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 'C17 H20 N8 S4' _chemical_formula_weight 464.65 _chemical_melting_point 180 _chemical_name_common Pyrazolo[3,4-d]pyrimidine _chemical_name_systematic ; 1-[4,6-dimethylthio-2H-pyrazolo[3,4-d]pyrimidin-2-yl]-4,6-dimethylthio-1H- pyrazolo[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' _cell_angle_alpha 90.00 _cell_angle_beta 97.92(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.620(2) _cell_length_b 10.411(2) _cell_length_c 26.813(5) _cell_measurement_reflns_used 42 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 13.1 _cell_measurement_theta_min 4.7 _cell_volume 2106.8(8) _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 SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device '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 .0593 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 3697 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.10 _diffrn_standards_decay_% nil _diffrn_standards_interval_count 97 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .473 _exptl_absorpt_correction_T_max .778 _exptl_absorpt_correction_T_min .749 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(local program; Karcher, 1981)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_meas ? _exptl_crystal_description Rhombehedral _exptl_crystal_F_000 968 _exptl_crystal_size_max .5 _exptl_crystal_size_mid .5 _exptl_crystal_size_min .5 _refine_diff_density_max .495 _refine_diff_density_min -.244 _refine_ls_extinction_coef .0066(12) _refine_ls_extinction_method 'SHELXL93 (Sheldrick, 1993)' _refine_ls_goodness_of_fit_all .836 _refine_ls_goodness_of_fit_ref .804 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 267 _refine_ls_number_reflns 3684 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .839 _refine_ls_restrained_S_obs .804 _refine_ls_R_factor_all .0656 _refine_ls_R_factor_gt .0519 _refine_ls_shift/esd_mean .000 _refine_ls_shift/su_max <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.1195P)^2^+1.4563P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_all .1688 _refine_ls_wR_factor_ref .1424 _reflns_number_gt 2893 _reflns_number_total 3697 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file vj1110.cif _[local]_cod_data_source_block 4 _[local]_cod_cif_authors_sg_H-M 'P 21/n' _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 ; _cod_database_code 2011584 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 .078(2) .0427(12) .0505(13) -.0017(11) .0118(11) -.0015(10) N2 .0745(15) .0433(12) .0470(13) .0038(11) .0115(11) -.0036(10) C3 .073(2) .0432(14) .0488(15) .0018(13) .0060(13) -.0006(12) C3A .063(2) .0458(15) .0463(14) .0005(12) .0051(12) .0002(11) C4 .063(2) .050(2) .050(2) -.0019(13) .0050(12) .0020(12) S4 .0962(6) .0473(5) .0581(5) -.0031(4) .0150(4) .0050(3) CS4 .142(4) .079(3) .055(2) -.008(2) .016(2) .016(2) N5 .074(2) .0537(14) .0487(13) -.0033(12) .0112(11) -.0025(11) C6 .068(2) .052(2) .052(2) -.0037(13) .0099(13) -.0053(13) S6 .1145(8) .0630(6) .0581(5) -.0143(5) .0293(5) -.0147(4) CS6 .121(3) .056(2) .082(2) -.009(2) .029(2) -.014(2) N7 .0728(15) .0464(13) .0503(13) -.0019(11) .0118(11) -.0058(11) C7A .060(2) .0452(15) .0499(15) -.0013(12) .0082(12) -.0018(12) N1' .075(2) .0464(13) .0457(12) -.0013(11) .0110(11) .0057(10) N2' .098(2) .0514(14) .0431(13) -.0026(13) .0110(13) .0074(11) C3' .095(2) .054(2) .0391(14) -.006(2) .0089(14) .0025(12) C3'A .070(2) .0463(15) .0404(13) -.0007(12) .0081(12) .0034(11) C4' .066(2) .0481(15) .0384(13) -.0036(12) .0094(11) .0003(11) S4' .1196(8) .0501(5) .0433(4) .0001(4) .0217(4) -.0020(3) CS4' .123(3) .053(2) .066(2) .002(2) .034(2) .002(2) N5' .0686(14) .0491(13) .0392(12) -.0038(11) .0117(10) .0003(10) C6' .0591(15) .051(2) .0419(14) -.0044(12) .0099(11) .0046(11) S6' .0832(5) .0554(5) .0419(4) .0003(4) .0195(3) .0077(3) CS6' .093(2) .053(2) .059(2) -.001(2) .022(2) .0131(14) N7' .0699(15) .0465(13) .0418(12) .0016(11) .0145(10) .0033(9) C7'A .064(2) .0465(14) .0411(13) .0025(12) .0066(11) .0034(11) C8 .079(2) .057(2) .047(2) .0041(15) .0140(14) -.0043(13) C9 .092(2) .0400(14) .048(2) -.0001(14) .0184(14) .0036(12) C10 .081(2) .046(2) .055(2) .0105(14) .0164(14) .0041(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 .6765(3) .7323(2) .27058(10) .0567(6) Uani d . 1 . N N2 .6687(3) .6147(2) .24806(9) .0546(6) Uani d . 1 . N C3 .6296(4) .5188(3) .27724(11) .0552(7) Uani d . 1 . C H3 .6191(4) .4323(3) .26873(11) .066 Uiso calc R 1 . H C3A .6076(4) .5743(3) .32313(11) .0519(6) Uani d . 1 . C C4 .5678(4) .5361(3) .37090(11) .0546(7) Uani d . 1 . C S4 .52861(13) .37328(8) .38199(3) .0668(3) Uani d . 1 . S CS4 .5173(7) .3728(4) .44831(14) .0915(13) Uani d . 1 . C HS4A .476(4) .2907(12) .4580(3) .137 Uiso calc R 1 . H HS4B .437(4) .439(2) .4561(2) .137 Uiso calc R 1 . H HS4C .6330(11) .389(3) .46636(14) .137 Uiso calc R 1 . H N5 .5591(4) .6212(3) .40670(9) .0586(6) Uani d . 1 . N C6 .5897(4) .7470(3) .39526(12) .0571(7) Uani d . 1 . C S6 .57146(15) .84538(9) .44724(3) .0769(3) Uani d . 1 . S CS6 .5919(6) 1.0034(4) .4224(2) .0850(11) Uani d . 1 . C HS6A .7103(13) 1.0157(11) .4148(11) .128 Uiso calc R 1 . H HS6B .567(4) 1.0659(4) .4467(5) .128 Uiso calc R 1 . H HS6C .509(3) 1.0134(11) .3921(7) .128 Uiso calc R 1 . H N7 .6293(3) .7968(2) .35316(9) .0562(6) Uani d . 1 . N C7A .6375(4) .7067(3) .31652(11) .0517(6) Uani d . 1 . C N1' .3980(3) .5145(2) .11726(9) .0553(6) Uani d . 1 . N N2' .4251(4) .5241(3) .06768(9) .0641(7) Uani d . 1 . N C3' .4362(5) .4053(3) .05171(11) .0626(8) Uani d . 1 . C H3' .4538(5) .3832(3) .01917(11) .075 Uiso calc R 1 . H C3'A .4178(4) .3152(3) .09027(10) .0522(6) Uani d . 1 . C C4' .4195(4) .1828(3) .09828(10) .0505(6) Uani d . 1 . C S4' .44824(14) .08063(8) .04922(3) .0700(3) Uani d . 1 . S CS4' .4605(6) -.0718(3) .07966(14) .0786(10) Uani d . 1 . C HS4D .5710(18) -.0788(12) .1015(9) .118 Uiso calc R 1 . H HS4E .453(4) -.1387(3) .0548(2) .118 Uiso calc R 1 . H HS4F .364(2) -.0802(12) .0991(9) .118 Uiso calc R 1 . H N5' .3991(3) .1360(2) .14339(8) .0519(6) Uani d . 1 . N C6' .3743(4) .2208(3) .18009(10) .0506(6) Uani d . 1 . C S6' .34088(11) .15980(7) .23887(3) .0592(3) Uani d . 1 . S CS6' .3691(5) -.0101(3) .23178(13) .0671(8) Uani d . 1 . C HS6D .348(4) -.0531(4) .2620(4) .101 Uiso calc R 1 . H HS6E .4878(11) -.0275(4) .2255(10) .101 Uiso calc R 1 . H HS6F .287(2) -.0407(5) .2040(6) .101 Uiso calc R 1 . H N7' .3715(3) .3477(2) .17775(9) .0521(6) Uani d . 1 . N C7'A .3946(4) .3903(3) .13179(10) .0505(6) Uani d . 1 . C C8 .7079(4) .6063(3) .19635(11) .0606(7) Uani d . 1 . C H8A .7015(4) .5172(3) .18565(11) .073 Uiso calc R 1 . H H8B .8277(4) .6364(3) .19510(11) .073 Uiso calc R 1 . H C9 .5800(4) .6852(3) .16051(11) .0591(7) Uani d . 1 . C H9A .5692(4) .7696(3) .17511(11) .071 Uiso calc R 1 . H H9B .6297(4) .6966(3) .12940(11) .071 Uiso calc R 1 . H C10 .3986(4) .6287(3) .14827(12) .0600(8) Uani d . 1 . C H10A .3537(4) .6070(3) .17934(12) .072 Uiso calc R 1 . H H10B .3200(4) .6923(3) .13074(12) .072 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 .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' 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 103.2(2) C3 N2 N1 114.5(2) C3 N2 C8 127.3(2) N1 N2 C8 118.2(2) N2 C3 C3A 105.9(3) N2 C3 H3 127.1(2) C3A C3 H3 127.1(2) C3 C3A C7A 104.7(3) C3 C3A C4 138.8(3) C7A C3A C4 116.5(3) N5 C4 C3A 120.7(3) N5 C4 S4 120.0(2) C3A C4 S4 119.2(2) C4 S4 CS4 101.7(2) S4 CS4 HS4A 109.47(14) S4 CS4 HS4B 109.5(2) HS4A CS4 HS4B 109.5 S4 CS4 HS4C 109.5(2) HS4A CS4 HS4C 109.5 HS4B CS4 HS4C 109.5 C4 N5 C6 116.9(3) N7 C6 N5 129.4(3) N7 C6 S6 120.4(2) N5 C6 S6 110.2(2) C6 S6 CS6 102.7(2) S6 CS6 HS6A 109.5(2) S6 CS6 HS6B 109.47(13) HS6A CS6 HS6B 109.5 S6 CS6 HS6C 109.47(14) HS6A CS6 HS6C 109.5 HS6B CS6 HS6C 109.5 C6 N7 C7A 112.7(3) N1 C7A N7 124.4(3) N1 C7A C3A 111.8(2) N7 C7A C3A 123.8(3) C7'A N1' N2' 111.0(2) C7'A N1' C10 128.1(2) N2' N1' C10 120.4(2) C3' N2' N1' 105.7(2) N2' C3' C3'A 111.6(3) N2' C3' H3' 124.2(2) C3'A C3' H3' 124.2(2) C4' C3'A C7'A 115.6(3) C4' C3'A C3' 140.1(3) C7'A C3'A C3' 104.4(3) N5' C4' C3'A 120.1(3) N5' C4' S4' 120.5(2) C3'A C4' S4' 119.4(2) C4' S4' CS4' 101.8(2) S4' CS4' HS4D 109.5(2) S4' CS4' HS4E 109.47(12) HS4D CS4' HS4E 109.5 S4' CS4' HS4F 109.47(13) HS4D CS4' HS4F 109.5 HS4E CS4' HS4F 109.5 C4' N5' C6' 117.8(2) N7' C6' N5' 128.3(3) N7' C6' S6' 113.7(2) N5' C6' S6' 118.0(2) C6' S6' CS6' 103.2(2) S6' CS6' HS6D 109.47(11) S6' CS6' HS6E 109.47(12) HS6D CS6' HS6E 109.5 S6' CS6' HS6F 109.47(12) HS6D CS6' HS6F 109.5 HS6E CS6' HS6F 109.5 C6' N7' C7'A 111.7(2) N7' C7'A N1' 126.2(3) N7' C7'A C3'A 126.5(3) N1' C7'A C3'A 107.3(2) N2 C8 C9 111.8(2) N2 C8 H8A 109.2(2) C9 C8 H8A 109.2(2) N2 C8 H8B 109.2(2) C9 C8 H8B 109.2(2) H8A C8 H8B 107.9 C10 C9 C8 114.9(3) C10 C9 H9A 108.6(2) C8 C9 H9A 108.6(2) C10 C9 H9B 108.6(2) C8 C9 H9B 108.6(2) H9A C9 H9B 107.5 N1' C10 C9 112.2(3) N1' C10 H10A 109.2(2) C9 C10 H10A 109.2(2) N1' C10 H10B 109.2(2) C9 C10 H10B 109.2(2) H10A C10 H10B 107.9 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 . 1.333(4) ? N1 N2 . 1.363(3) ? N2 C3 . 1.327(4) ? N2 C8 . 1.461(4) ? C3 C3A . 1.390(4) ? C3 H3 . .93 ? C3A C7A . 1.412(4) ? C3A C4 . 1.413(4) ? C4 N5 . 1.315(4) ? C4 S4 . 1.754(3) ? S4 CS4 . 1.792(4) ? CS4 HS4A . .96 ? CS4 HS4B . .96 ? CS4 HS4C . .96 ? N5 C6 . 1.372(4) ? C6 N7 . 1.314(4) ? C6 S6 . 1.750(3) ? S6 CS6 . 1.790(4) ? CS6 HS6A . .96 ? CS6 HS6B . .96 ? CS6 HS6C . .96 ? N7 C7A . 1.366(4) ? N1' C7'A . 1.352(4) ? N1' N2' . 1.377(3) ? N1' C10 . 1.450(4) ? N2' C3' . 1.315(4) ? C3' C3'A . 1.417(4) ? C3' H3' . .93 ? C3'A C4' . 1.395(4) ? C3'A C7'A . 1.391(4) ? C4' N5' . 1.333(3) ? C4' S4' . 1.729(3) ? S4' CS4' . 1.782(4) ? CS4' HS4D . .96 ? CS4' HS4E . .96 ? CS4' HS4F . .96 ? N5' C6' . 1.355(4) ? C6' N7' . 1.323(4) ? C6' S6' . 1.750(3) ? S6' CS6' . 1.795(3) ? CS6' HS6D . .96 ? CS6' HS6E . .96 ? CS6' HS6F . .96 ? N7' C7'A . 1.344(3) ? C8 C9 . 1.513(4) ? C8 H8A . .97 ? C8 H8B . .97 ? C9 C10 . 1.496(5) ? C9 H9A . .97 ? C9 H9B . .97 ? C10 H10A . .97 ? C10 H10B . .97 ? 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 -.7(3) C7A N1 N2 C8 -179.1(2) N1 N2 C3 C3A .4(3) C8 N2 C3 C3A 178.6(3) N2 C3 C3A C7A .1(3) N2 C3 C3A C4 -179.3(3) C3 C3A C4 N5 179.6(3) C7A C3A C4 N5 .3(4) C3 C3A C4 S4 -.8(5) C7A C3A C4 S4 179.9(2) N5 C4 S4 CS4 -8.3(3) C3A C4 S4 CS4 172.1(3) C3A C4 N5 C6 .1(4) S4 C4 N5 C6 -179.4(2) C4 N5 C6 N7 -.8(5) C4 N5 C6 S6 179.8(2) N7 C6 S6 CS6 6.5(3) N5 C6 S6 CS6 -174.0(2) N5 C6 N7 C7A .9(5) S6 C6 N7 C7A -179.8(2) N2 N1 C7A N7 179.9(3) N2 N1 C7A C3A .7(3) C6 N7 C7A N1 -179.5(3) C6 N7 C7A C3A -.3(4) C3 C3A C7A N1 -.5(3) C4 C3A C7A N1 179.0(3) C3 C3A C7A N7 -179.7(3) C4 C3A C7A N7 -.2(4) C7'A N1' N2' C3' .7(4) C10 N1' N2' C3' 173.3(3) N1' N2' C3' C3'A -.4(4) N2' C3' C3'A C4' -178.7(4) N2' C3' C3'A C7'A -.1(4) C7'A C3'A C4' N5' .2(4) C3' C3'A C4' N5' 178.6(4) C7'A C3'A C4' S4' -179.8(2) C3' C3'A C4' S4' -1.3(6) N5' C4' S4' CS4' -5.0(3) C3'A C4' S4' CS4' 174.9(3) C3'A C4' N5' C6' 1.0(4) S4' C4' N5' C6' -179.0(2) C4' N5' C6' N7' -1.8(4) C4' N5' C6' S6' 178.1(2) N7' C6' S6' CS6' -175.6(2) N5' C6' S6' CS6' 4.4(3) N5' C6' N7' C7'A 1.0(4) S6' C6' N7' C7'A -178.9(2) C6' N7' C7'A N1' 179.8(3) C6' N7' C7'A C3'A .5(4) N2' N1' C7'A N7' 179.7(3) C10 N1' C7'A N7' 7.9(5) N2' N1' C7'A C3'A -.8(3) C10 N1' C7'A C3'A -172.7(3) C4' C3'A C7'A N7' -1.0(5) C3' C3'A C7'A N7' -180.0(3) C4' C3'A C7'A N1' 179.5(3) C3' C3'A C7'A N1' .5(3) C3 N2 C8 C9 120.9(3) N1 N2 C8 C9 -60.9(4) N2 C8 C9 C10 -74.3(3) C7'A N1' C10 C9 100.5(4) N2' N1' C10 C9 -70.6(4) C8 C9 C10 N1' -69.9(3)