#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/47/2014722.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_2014722 loop_ _publ_author_name 'Seela, Frank' 'Sirivolu, Venkata Ramana' 'He, Junlin' 'Eickmeier, Henning' _publ_section_title ;3-Bromo-1-(2-deoxy-\b-D-erythro-pentofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine: a nucleoside which strongly enhances DNA duplex stability ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o67 _journal_page_last o69 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C10 H13 Br N6 O3' _chemical_formula_moiety 'C10 H13 Br N6 O3' _chemical_formula_sum 'C10 H13 Br N6 O3' _chemical_formula_weight 345.17 _chemical_name_systematic ; 3-Bromo-1-(2-deoxy-\b-D-erythro-pentofuranosyl)-1H- pyrazolo[3,4-d]pyrimidine-4,6-diamine ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.5939(10) _cell_length_b 9.2822(18) _cell_length_c 18.164(2) _cell_measurement_reflns_used 42 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 12.49 _cell_measurement_theta_min 4.99 _cell_volume 1280.3(3) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_data_reduction 'SHELXTL (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL (Sheldrick, 1997) and PLATON (Spek, 1999)' _computing_structure_refinement SHELXTL _computing_structure_solution SHELXTL _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '2\q/\w scans' _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 0.0423 _diffrn_reflns_av_sigmaI/netI 0.0695 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 4231 _diffrn_reflns_theta_full 30.00 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_theta_min 2.24 _diffrn_standards_decay_% none _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 3.230 _exptl_absorpt_correction_T_max 0.5194 _exptl_absorpt_correction_T_min 0.3155 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SHELXTL; Sheldrick,1997)' _exptl_crystal_colour 'light brown' _exptl_crystal_density_diffrn 1.791 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'transparent plate' _exptl_crystal_F_000 696 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.443 _refine_diff_density_min -0.887 _refine_ls_abs_structure_details 'Flack (1983), 1536 Friedel pairs?' _refine_ls_abs_structure_Flack 0.020(16) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 199 _refine_ls_number_reflns 3682 _refine_ls_number_restraints 8 _refine_ls_restrained_S_all 1.064 _refine_ls_R_factor_all 0.0909 _refine_ls_R_factor_gt 0.0563 _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^)+(0.0688P)^2^+0.0128P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1224 _refine_ls_wR_factor_ref 0.1394 _reflns_number_gt 2568 _reflns_number_total 3682 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1785.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P21 21 21' _cod_database_code 2014722 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -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 0.1137(6) 0.9773(4) 0.02381(18) 0.0331(8) Uani d . 1 . . N N2 0.1220(7) 1.0731(4) 0.0832(2) 0.0385(9) Uani d . 1 . . N C3 0.1229(8) 1.2003(5) 0.0532(2) 0.0344(10) Uani d . 1 . . C Br3 0.13107(9) 1.36522(5) 0.11197(3) 0.05024(19) Uani d . 1 . . Br C3A 0.1134(7) 1.1953(4) -0.0250(2) 0.0319(9) Uani d . 1 . . C N4 0.1244(10) 1.4340(4) -0.0763(3) 0.0543(13) Uani d D 1 . . N H4A 0.116(9) 1.484(6) -0.113(2) 0.065 Uiso d D 1 . . H H4B 0.147(10) 1.483(7) -0.040(2) 0.065 Uiso d D 1 . . H C4 0.1138(8) 1.2912(5) -0.0859(3) 0.0355(10) Uani d . 1 . . C N5 0.1009(5) 1.2375(4) -0.1540(2) 0.0337(9) Uani d . 1 . . N N6 0.0690(6) 1.0447(5) -0.2317(2) 0.0391(10) Uani d D 1 . . N H6A 0.051(8) 0.959(2) -0.241(3) 0.047 Uiso d D 1 . . H H6B 0.026(7) 1.091(6) -0.266(2) 0.047 Uiso d D 1 . . H C6 0.0872(6) 1.0917(5) -0.1615(3) 0.0309(10) Uani d . 1 . . C N7 0.0927(5) 0.9922(4) -0.1089(2) 0.0294(8) Uani d . 1 . . N C7A 0.1076(6) 1.0491(4) -0.0409(2) 0.0272(9) Uani d . 1 . . C C1' 0.1025(6) 0.8241(4) 0.0377(2) 0.0270(9) Uani d . 1 . . C H1' 0.1193 0.7721 -0.0087 0.032 Uiso calc R 1 . . H C2' 0.2376(6) 0.7714(5) 0.0933(2) 0.0319(10) Uani d . 1 . . C H2'1 0.2823 0.6772 0.0797 0.038 Uiso calc R 1 . . H H2'2 0.3356 0.8381 0.0969 0.038 Uiso calc R 1 . . H C3' 0.1370(6) 0.7642(4) 0.1656(2) 0.0294(8) Uani d D 1 . . C H3'1 0.1427 0.8570 0.1912 0.035 Uiso calc R 1 . . H O3' 0.1963(5) 0.6507(4) 0.21257(18) 0.0411(8) Uani d D 1 . . O H3' 0.224(8) 0.6834(18) 0.2528(12) 0.062 Uiso d D 1 . . H C4' -0.0522(6) 0.7333(5) 0.1399(2) 0.0262(9) Uani d . 1 . . C H4' -0.0709 0.6288 0.1385 0.031 Uiso calc R 1 . . H O4' -0.0644(4) 0.7896(4) 0.06659(17) 0.0387(8) Uani d . 1 . . O C5' -0.1878(6) 0.8004(6) 0.1888(3) 0.0397(12) Uani d D 1 . . C H5'1 -0.1831 0.7542 0.2367 0.048 Uiso calc R 1 . . H H5'2 -0.1589 0.9014 0.1957 0.048 Uiso calc R 1 . . H O5' -0.3636(5) 0.7899(3) 0.16080(18) 0.0354(7) Uani d D 1 . . O H5' -0.380(3) 0.7079(19) 0.145(3) 0.053 Uiso d D 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 0.050(2) 0.0267(17) 0.0221(16) 0.0028(19) -0.0005(18) -0.0001(13) N2 0.057(3) 0.0312(19) 0.0278(18) 0.006(2) -0.006(2) -0.0016(15) C3 0.044(3) 0.031(2) 0.028(2) 0.003(2) -0.003(2) -0.0009(16) Br3 0.0810(4) 0.0313(2) 0.0384(2) 0.0058(3) -0.0074(3) -0.0074(2) C3A 0.043(3) 0.0255(19) 0.027(2) 0.003(2) -0.001(2) 0.0037(16) N4 0.090(4) 0.027(2) 0.045(3) -0.006(3) -0.007(3) 0.0096(18) C4 0.040(3) 0.029(2) 0.038(2) -0.002(2) -0.004(2) 0.0052(17) N5 0.039(2) 0.0332(18) 0.0283(18) -0.0039(18) -0.0010(18) 0.0093(15) N6 0.053(3) 0.038(2) 0.026(2) -0.0036(19) -0.0040(18) 0.0042(17) C6 0.030(2) 0.034(2) 0.029(2) -0.0009(17) 0.0018(18) 0.0022(17) N7 0.034(2) 0.0275(16) 0.0268(17) 0.0018(14) -0.0004(17) 0.0012(15) C7A 0.032(2) 0.0251(18) 0.0245(19) -0.0004(19) -0.0019(19) 0.0050(15) C1' 0.032(2) 0.0218(17) 0.0272(19) 0.0005(17) 0.0015(18) 0.0024(14) C2' 0.032(2) 0.029(2) 0.035(3) -0.0006(19) 0.0027(18) 0.0079(17) C3' 0.035(2) 0.0231(18) 0.030(2) 0.001(2) -0.007(2) 0.0017(15) O3' 0.055(2) 0.0349(18) 0.0338(17) 0.0072(16) -0.0137(15) 0.0061(14) C4' 0.036(2) 0.0213(18) 0.0214(18) 0.0006(17) -0.0053(17) -0.0021(15) O4' 0.0308(17) 0.057(2) 0.0280(16) -0.0078(15) -0.0055(13) 0.0124(16) C5' 0.039(3) 0.046(3) 0.033(2) 0.002(2) -0.002(2) -0.012(2) O5' 0.0350(17) 0.0335(16) 0.0376(16) 0.0008(16) -0.0001(16) -0.0087(13) 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 . 1.353(5) no N1 N2 . 1.400(5) no N1 C1' . 1.447(5) yes N2 C3 . 1.301(6) no C3 C3A . 1.423(6) no C3 Br3 . 1.868(4) yes C3A C7A . 1.388(6) no C3A C4 . 1.420(6) no N4 C4 . 1.340(6) yes N4 H4A . 0.82(5) no N4 H4B . 0.82(5) no C4 N5 . 1.337(6) no N5 C6 . 1.364(6) no N6 C6 . 1.355(6) yes N6 H6A . 0.824(10) no N6 H6B . 0.82(5) no C6 N7 . 1.331(6) no N7 C7A . 1.347(6) no C1' O4' . 1.408(5) yes C1' C2' . 1.520(6) no C1' H1' . 0.9800 no C2' C3' . 1.520(6) no C2' H2'1 . 0.9700 no C2' H2'2 . 0.9700 no C3' O3' . 1.428(5) no C3' C4' . 1.538(6) no C3' H3'1 . 0.9800 no O3' H3' . 0.82(3) no C4' O4' . 1.433(5) yes C4' C5' . 1.497(6) no C4' H4' . 0.9800 no C5' O5' . 1.432(6) no C5' H5'1 . 0.9700 no C5' H5'2 . 0.9700 no O5' H5' . 0.82(2) no 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' Br Br -0.2901 2.4595 '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 C7A N1 N2 111.0(3) no C7A N1 C1' 129.4(4) yes N2 N1 C1' 119.5(3) yes C3 N2 N1 104.7(4) no N2 C3 C3A 112.9(4) no N2 C3 Br3 120.3(3) yes C3A C3 Br3 126.8(3) yes C7A C3A C4 116.8(4) no C7A C3A C3 104.0(4) no C4 C3A C3 139.2(4) no C4 N4 H4A 117(5) no C4 N4 H4B 132(5) no H4A N4 H4B 112(7) no N5 C4 N4 119.6(4) yes N5 C4 C3A 119.1(4) no N4 C4 C3A 121.2(4) no C4 N5 C6 117.9(4) no C6 N6 H6A 121(4) no C6 N6 H6B 126(4) no H6A N6 H6B 106(6) no N7 C6 N6 117.1(4) no N7 C6 N5 127.9(4) no N6 C6 N5 115.0(4) yes C6 N7 C7A 112.9(4) no N7 C7A N1 127.3(4) no N7 C7A C3A 125.2(4) no N1 C7A C3A 107.4(4) no O4' C1' N1 109.9(4) yes O4' C1' C2' 106.7(3) no N1 C1' C2' 113.1(4) yes O4' C1' H1' 109.0 no N1 C1' H1' 109.0 no C2' C1' H1' 109.0 no C3' C2' C1' 104.4(4) no C3' C2' H2'1 110.9 no C1' C2' H2'1 110.9 no C3' C2' H2'2 110.9 no C1' C2' H2'2 110.9 no H2'1 C2' H2'2 108.9 no O3' C3' C2' 112.9(4) no O3' C3' C4' 109.8(3) no C2' C3' C4' 102.5(3) no O3' C3' H3'1 110.5 no C2' C3' H3'1 110.5 no C4' C3' H3'1 110.5 no C3' O3' H3' 110.0(11) no O4' C4' C5' 110.8(4) yes O4' C4' C3' 105.9(3) no C5' C4' C3' 112.6(4) no O4' C4' H4' 109.1 no C5' C4' H4' 109.1 no C3' C4' H4' 109.1 no C1' O4' C4' 111.8(3) yes O5' C5' C4' 113.7(4) no O5' C5' H5'1 108.8 no C4' C5' H5'1 108.8 no O5' C5' H5'2 108.8 no C4' C5' H5'2 108.8 no H5'1 C5' H5'2 107.7 no C5' O5' H5' 109.2(11) no 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 N4 H4A O5' 4_575 0.82(5) 2.28(4) 2.989(5) 146(6) N6 H6B O5' 2_474 0.82(5) 2.12(5) 2.933(5) 167(6) O3' H3' N5 2_575 0.82(3) 2.27(2) 3.053(5) 159(6) O5' H5' N7 4_465 0.82(2) 1.98(3) 2.803(5) 177.0(17) 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 C7A N1 N2 C3 -0.7(6) yes C1' N1 N2 C3 -177.2(5) yes N1 N2 C3 C3A 0.7(7) no N1 N2 C3 Br3 179.4(4) no N2 C3 C3A C7A -0.4(7) no Br3 C3 C3A C7A -179.0(4) no N2 C3 C3A C4 -178.0(7) no Br3 C3 C3A C4 3.4(11) yes C7A C3A C4 N5 2.9(8) no C3 C3A C4 N5 -179.7(7) no C7A C3A C4 N4 -178.0(6) no C3 C3A C4 N4 -0.7(12) no N4 C4 N5 C6 -178.9(6) no C3A C4 N5 C6 0.2(8) no C4 N5 C6 N7 -3.2(8) no C4 N5 C6 N6 178.0(5) yes N6 C6 N7 C7A -178.8(4) no N5 C6 N7 C7A 2.4(7) no C6 N7 C7A N1 178.9(5) no C6 N7 C7A C3A 1.3(7) no N2 N1 C7A N7 -177.4(5) no C1' N1 C7A N7 -1.4(9) no N2 N1 C7A C3A 0.5(7) no C1' N1 C7A C3A 176.6(5) no C4 C3A C7A N7 -3.9(9) yes C3 C3A C7A N7 177.9(5) no C4 C3A C7A N1 178.1(5) no C3 C3A C7A N1 -0.1(7) no C7A N1 C1' O4' -105.0(6) yes N2 N1 C1' O4' 70.7(6) yes C7A N1 C1' C2' 135.8(5) no N2 N1 C1' C2' -48.4(6) no O4' C1' C2' C3' -22.9(4) no N1 C1' C2' C3' 98.1(4) yes C1' C2' C3' O3' 147.2(4) no C1' C2' C3' C4' 29.2(4) yes O3' C3' C4' O4' -146.1(3) no C2' C3' C4' O4' -25.9(4) yes O3' C3' C4' C5' 92.6(5) no C2' C3' C4' C5' -147.2(4) yes N1 C1' O4' C4' -116.6(4) yes C2' C1' O4' C4' 6.4(5) yes C5' C4' O4' C1' 135.0(4) yes C3' C4' O4' C1' 12.6(4) yes O4' C4' C5' O5' 53.6(6) no C3' C4' C5' O5' 172.0(4) yes