#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/52/2015260.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_2015260 loop_ _publ_author_name 'Seela, Frank' 'Chittepu, Padmaja' 'Eickmeier, Henning' _publ_section_title ;4-Amino-7-(2-deoxy-2-fluoro-\b-D-arabinofuranosyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine: a bis-fluorinated analogue of 2'-deoxytubercidin ; _journal_coeditor_code JZ3003 _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o231 _journal_page_last o233 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C11 H12 F2 N4 O3' _chemical_formula_moiety 'C11 H12 F2 N4 O3' _chemical_formula_sum 'C11 H12 F2 N4 O3' _chemical_formula_weight 286.25 _chemical_name_systematic ; 4-Amino-7-(2-deoxy-2-fluoro-\b-D-arabinofuranosyl)-5-fluoro- 7H-pyrrolo[2,3-d]pyrimidine ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _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 97.856(9) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 5.7355(6) _cell_length_b 9.8374(13) _cell_length_c 10.9428(13) _cell_measurement_reflns_used 54 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 12.53 _cell_measurement_theta_min 5.47 _cell_volume 611.62(13) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_data_reduction 'SHELXTL (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL 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 _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 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 2846 _diffrn_reflns_theta_full 30.99 _diffrn_reflns_theta_max 30.99 _diffrn_reflns_theta_min 1.88 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 296 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.324 _refine_diff_density_min -0.211 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 188 _refine_ls_number_reflns 2056 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.045 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0385 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+0.0481P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0969 _refine_ls_wR_factor_ref 0.1015 _reflns_number_gt 1809 _reflns_number_total 2056 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file jz3003.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21' _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 ; _cod_database_code 2015260 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_type_symbol _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 N N1 0.5981(3) 0.9121(2) 0.26365(14) 0.0376(4) Uani d . 1 C C2 0.4549(5) 0.9870(3) 0.32462(18) 0.0402(5) Uani d . 1 H H2 0.3428 1.0388 0.2757 0.048 Uiso calc R 1 N N3 0.4528(4) 0.9966(2) 0.44545(15) 0.0364(4) Uani d . 1 C C4 0.6171(3) 0.9177(2) 0.50863(15) 0.0280(4) Uani d . 1 C C5 0.7753(4) 0.8333(2) 0.45896(16) 0.0309(4) Uani d . 1 C C6 0.7613(4) 0.8336(2) 0.32917(17) 0.0333(4) Uani d . 1 N N6 0.9026(4) 0.7559(3) 0.26887(19) 0.0505(6) Uani d . 1 H H6A 0.8873 0.7572 0.1896 0.061 Uiso calc R 1 H H6B 1.0078 0.7052 0.3097 0.061 Uiso calc R 1 C C7 0.9142(4) 0.7713(3) 0.5617(2) 0.0382(5) Uani d . 1 F F7 1.0868(3) 0.6806(2) 0.55244(16) 0.0637(5) Uani d . 1 C C8 0.8439(4) 0.8166(3) 0.66739(19) 0.0364(4) Uani d . 1 H H8 0.9066 0.7915 0.7471 0.044 Uiso calc R 1 N N9 0.6595(3) 0.9083(2) 0.63497(13) 0.0305(3) Uani d . 1 C C1' 0.5435(4) 0.9910(2) 0.71657(16) 0.0313(4) Uani d . 1 H H1' 0.4312 1.0513 0.6676 0.038 Uiso calc R 1 C C2' 0.4155(4) 0.9118(2) 0.80942(16) 0.0309(4) Uani d . 1 H H2' 0.2558 0.9482 0.8071 0.037 Uiso calc R 1 F F2' 0.4021(3) 0.77445(17) 0.78432(14) 0.0533(4) Uani d . 1 O O3' 0.4053(3) 0.93855(18) 1.02730(11) 0.0338(3) Uani d D 1 H H3' 0.486(4) 0.927(4) 1.0944(13) 0.051 Uiso d D 1 C C3' 0.5540(3) 0.94184(19) 0.93427(15) 0.0246(3) Uani d . 1 H H3'1 0.6820 0.8759 0.9528 0.029 Uiso calc R 1 C C4' 0.6543(3) 1.0824(2) 0.91300(15) 0.0257(3) Uani d . 1 H H4' 0.5325 1.1519 0.9149 0.031 Uiso calc R 1 O O4' 0.7188(3) 1.07168(19) 0.79053(13) 0.0426(4) Uani d . 1 O O5' 0.9562(3) 1.25163(15) 0.98599(16) 0.0374(4) Uani d D 1 H H5' 0.848(4) 1.307(3) 0.974(3) 0.056 Uiso d D 1 C C5' 0.8694(3) 1.1182(2) 1.00292(18) 0.0301(4) Uani d . 1 H H5'1 0.8310 1.1104 1.0862 0.036 Uiso calc R 1 H H5'2 0.9929 1.0530 0.9941 0.036 Uiso calc R 1 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 0.0480(10) 0.0471(10) 0.0186(6) 0.0027(10) 0.0082(6) -0.0020(7) C2 0.0506(12) 0.0481(12) 0.0218(8) 0.0106(11) 0.0042(8) 0.0030(9) N3 0.0456(10) 0.0430(10) 0.0212(6) 0.0102(9) 0.0064(7) 0.0004(7) C4 0.0330(8) 0.0340(9) 0.0173(6) 0.0002(8) 0.0051(6) -0.0013(7) C5 0.0337(9) 0.0374(10) 0.0225(7) 0.0033(8) 0.0074(7) -0.0028(8) C6 0.0385(9) 0.0390(11) 0.0239(8) -0.0029(9) 0.0097(7) -0.0061(8) N6 0.0551(12) 0.0659(15) 0.0336(9) 0.0138(12) 0.0167(8) -0.0094(10) C7 0.0356(10) 0.0440(12) 0.0345(9) 0.0085(10) 0.0032(8) -0.0016(9) F7 0.0560(9) 0.0775(13) 0.0558(9) 0.0359(10) 0.0008(7) -0.0057(9) C8 0.0371(9) 0.0454(12) 0.0252(8) 0.0033(10) -0.0009(7) 0.0017(8) N9 0.0355(8) 0.0396(9) 0.0162(6) 0.0027(8) 0.0034(5) 0.0008(6) C1' 0.0402(10) 0.0367(10) 0.0179(7) -0.0039(9) 0.0073(7) -0.0017(7) C2' 0.0346(9) 0.0389(10) 0.0196(7) -0.0097(9) 0.0056(6) -0.0065(7) F2' 0.0801(11) 0.0436(8) 0.0400(7) -0.0277(8) 0.0214(7) -0.0149(6) O3' 0.0349(7) 0.0497(9) 0.0181(5) -0.0051(7) 0.0089(5) -0.0002(6) C3' 0.0276(8) 0.0289(8) 0.0182(6) -0.0021(7) 0.0065(6) -0.0014(6) C4' 0.0314(8) 0.0279(8) 0.0182(6) -0.0020(7) 0.0053(6) -0.0025(6) O4' 0.0595(10) 0.0500(10) 0.0211(6) -0.0260(9) 0.0150(6) -0.0079(6) O5' 0.0303(7) 0.0356(8) 0.0476(9) -0.0076(7) 0.0098(6) -0.0072(7) C5' 0.0287(9) 0.0318(9) 0.0295(8) -0.0011(8) 0.0033(7) -0.0031(7) 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0000 '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 C6 N1 C2 118.58(17) no N3 C2 N1 128.4(2) no N3 C2 H2 115.8 no N1 C2 H2 115.8 no C2 N3 C4 111.85(18) no N3 C4 N9 125.06(17) no N3 C4 C5 126.44(16) no N9 C4 C5 108.49(17) no C4 C5 C6 116.14(18) no C4 C5 C7 105.73(16) no C6 C5 C7 138.1(2) no N1 C6 N6 119.07(19) no N1 C6 C5 118.55(18) no N6 C6 C5 122.4(2) no C6 N6 H6A 120.0 no C6 N6 H6B 120.0 no H6A N6 H6B 120.0 no F7 C7 C8 126.3(2) yes F7 C7 C5 124.21(19) yes C8 C7 C5 109.5(2) no C7 C8 N9 107.43(18) no C7 C8 H8 126.3 no N9 C8 H8 126.3 no C4 N9 C8 108.81(16) no C4 N9 C1' 123.65(17) yes C8 N9 C1' 127.29(16) yes N9 C1' O4' 108.33(17) no N9 C1' C2' 115.22(19) no O4' C1' C2' 105.46(14) yes N9 C1' H1' 109.2 no O4' C1' H1' 109.2 no C2' C1' H1' 109.2 no F2' C2' C3' 112.28(18) yes F2' C2' C1' 112.44(16) yes C3' C2' C1' 104.93(15) yes F2' C2' H2' 109.0 no C3' C2' H2' 109.0 no C1' C2' H2' 109.0 no C3' O3' H3' 109(2) no O3' C3' C2' 110.56(15) no O3' C3' C4' 114.01(15) no C2' C3' C4' 101.61(15) no O3' C3' H3'1 110.1 no C2' C3' H3'1 110.1 no C4' C3' H3'1 110.1 no O4' C4' C5' 109.37(15) no O4' C4' C3' 103.02(14) no C5' C4' C3' 113.75(15) no O4' C4' H4' 110.2 no C5' C4' H4' 110.2 no C3' C4' H4' 110.2 no C1' O4' C4' 108.33(14) no C5' O5' H5' 111(2) no O5' C5' C4' 113.51(17) no O5' C5' H5'1 108.9 no C4' C5' H5'1 108.9 no O5' C5' H5'2 108.9 no C4' C5' H5'2 108.9 no H5'1 C5' H5'2 107.7 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C6 1.343(3) no N1 C2 1.346(3) no C2 N3 1.327(2) no C2 H2 0.9300 no N3 C4 1.338(3) yes C4 N9 1.374(2) no C4 C5 1.394(3) yes C5 C6 1.412(2) yes C5 C7 1.423(3) no C6 N6 1.350(3) no N6 H6A 0.8600 no N6 H6B 0.8600 no C7 F7 1.346(3) yes C7 C8 1.352(3) no C8 N9 1.398(3) no C8 H8 0.9300 no N9 C1' 1.436(3) yes C1' O4' 1.440(3) yes C1' C2' 1.543(3) no C1' H1' 0.9800 no C2' F2' 1.379(3) yes C2' C3' 1.513(2) no C2' H2' 0.9800 no O3' C3' 1.415(2) no O3' H3' 0.821(17) no C3' C4' 1.527(3) no C3' H3'1 0.9800 no C4' O4' 1.442(2) yes C4' C5' 1.511(3) no C4' H4' 0.9800 no O5' C5' 1.425(3) no O5' H5' 0.82(3) no C5' H5'1 0.9700 no C5' H5'2 0.9700 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 N6 H6A O5' 2_746 0.86 2.23 3.009(3) 151 N6 H6B O4' 2_746 0.86 2.42 2.968(3) 122 O3' H3' N1 1_556 0.821(17) 1.882(15) 2.683(2) 165(3) O5' H5' O3' 2_657 0.82(3) 1.94(3) 2.760(2) 171(3) N6 H6B F7 . 0.86 2.64 3.225(3) 126 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 C6 N1 C2 N3 1.0(4) no N1 C2 N3 C4 -0.8(4) no C2 N3 C4 N9 178.8(2) no C2 N3 C4 C5 -0.3(3) no N3 C4 C5 C6 1.1(3) no N9 C4 C5 C6 -178.11(19) no N3 C4 C5 C7 179.7(2) no N9 C4 C5 C7 0.5(2) no C2 N1 C6 N6 178.6(2) no C2 N1 C6 C5 0.0(3) no C4 C5 C6 N1 -0.9(3) no C7 C5 C6 N1 -178.9(3) no C4 C5 C6 N6 -179.5(2) no C7 C5 C6 N6 2.5(4) no C4 C5 C7 F7 179.1(2) no C6 C5 C7 F7 -2.7(5) yes C4 C5 C7 C8 -0.3(3) no C6 C5 C7 C8 177.9(3) no F7 C7 C8 N9 -179.4(2) yes C5 C7 C8 N9 -0.1(3) no N3 C4 N9 C8 -179.8(2) no C5 C4 N9 C8 -0.6(2) no N3 C4 N9 C1' -5.1(3) no C5 C4 N9 C1' 174.12(19) no C7 C8 N9 C4 0.4(3) no C7 C8 N9 C1' -174.0(2) no C4 N9 C1' O4' -117.8(2) yes C8 N9 C1' O4' 55.9(3) yes C4 N9 C1' C2' 124.4(2) no C8 N9 C1' C2' -61.9(3) no N9 C1' C2' F2' -10.0(3) yes O4' C1' C2' F2' -129.45(19) yes N9 C1' C2' C3' 112.27(19) yes O4' C1' C2' C3' -7.1(2) no F2' C2' C3' O3' -87.7(2) yes C1' C2' C3' O3' 149.88(17) no F2' C2' C3' C4' 150.92(17) yes C1' C2' C3' C4' 28.5(2) no O3' C3' C4' O4' -159.14(15) no C2' C3' C4' O4' -40.19(18) yes O3' C3' C4' C5' 82.58(19) no C2' C3' C4' C5' -158.47(16) no N9 C1' O4' C4' -142.98(18) yes C2' C1' O4' C4' -19.1(2) yes C5' C4' O4' C1' 158.90(18) yes C3' C4' O4' C1' 37.6(2) yes O4' C4' C5' O5' 68.0(2) yes C3' C4' C5' O5' -177.46(15) yes _journal_paper_doi 10.1107/S0108270106007633