#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/35/2003549.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_2003549 loop_ _publ_author_name 'Groziak, M. P.' 'Lin, R.' 'Robinson, P. D.' _publ_section_title ; An Unusual C6-Spiro-Fused Cyclouridine Derivative ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1204 _journal_page_last 1207 _journal_volume 51 _journal_year 1995 _chemical_formula_moiety 'C13 H16 N2 O8' _chemical_formula_sum 'C13 H16 N2 O8' _chemical_formula_weight 328.28 _chemical_name_systematic ; [3S,4S,5R-(1\b,3\b,6\a,7\a,12a\b)]-hexahydro-1-hydroxy-6,6- dimethyl-3,13a:4,8-diepoxy-3H,6H-dioxolano[4,5-f] pyrimido[6,1-c][1,4]oxazonine-10,12(11H,13H)dione ; _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' _cell_angle_alpha 90.0 _cell_angle_beta 96.32(1) _cell_angle_gamma 90.0 _cell_formula_units_Z 2 _cell_length_a 7.569(1) _cell_length_b 9.738(2) _cell_length_c 9.503(1) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 19.92 _cell_measurement_theta_min 18.55 _cell_volume 696.18(19) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) ; _computing_data_reduction ; TEXSAN PROCESS (Molecular Structure Corporation, 1985) ; _computing_molecular_graphics 'TEXSAN ORTEP (Johnson, 1965)' _computing_publication_material 'TEXSAN FINISH' _computing_structure_refinement 'TEXSAN LS' _computing_structure_solution ; TEXSAN PROCESS (Molecular Structure Corporation, 1985) ; _diffrn_ambient_temperature 296 _diffrn_measurement_device 'Rigaku AFC5S' _diffrn_measurement_method '\w/2\q scans (rate 2\% min^-1^ in \w)' _diffrn_radiation_monochromator graphite _diffrn_radiation_source x-ray_tube _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.016 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 1405 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_min 1.75 _diffrn_standards_decay_% -0.6 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type none _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.566 _exptl_crystal_description prism _exptl_crystal_F_000 344 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.26 _refine_diff_density_min -0.19 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.96 _refine_ls_hydrogen_treatment ; H atoms riding (C---H, N---H 0.95\%A), except for H7 and H8 which were obtained from a difference map ; _refine_ls_matrix_type full _refine_ls_number_parameters 207 _refine_ls_number_reflns 1238 _refine_ls_R_factor_obs 0.035 _refine_ls_shift/esd_max 0.0001 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme 'w = 4F~o~^2^/\s^2^(F~o~^2^)' _refine_ls_wR_factor_obs 0.043 _reflns_number_observed 1238 _reflns_number_total 1302 _reflns_observed_criterion '[I > \s(I)]' _[local]_cod_data_source_file fg1041.cif _[local]_cod_data_source_block structure _[local]_cod_cif_authors_sg_H-M 'P 21' _[local]_cod_cif_authors_sg_Hall 'P 2y1' _cod_original_cell_volume 696.2(3) _cod_database_code 2003549 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,-z loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C ? International_Tables_Vol_IV_Table_2.3.1 .002 .002 H ? International_Tables_Vol_IV_Table_2.3.1 0 0 O ? International_Tables_Vol_IV_Table_2.3.1 .008 .006 N ? International_Tables_Vol_IV_Table_2.3.1 .004 .003 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_calc_attached_atom O2 0.1479(3) 0.3471 0.3925(2) 0.042(1) Uani ? ? O4 0.5519(4) 0.6156(4) 0.6423(3) 0.062(1) Uani ? ? O7 0.7494(3) 0.4079(4) 0.1546(2) 0.051(1) Uani ? ? O8 0.8158(3) 0.4517(5) 0.3907(3) 0.071(1) Uani ? ? O2' 0.0507(3) 0.4198(5) -0.0531(2) 0.064(1) Uani ? ? O3' 0.2511(3) 0.4079(4) -0.2090(2) 0.040(1) Uani ? ? O4' 0.4141(3) 0.3065(4) 0.0764(2) 0.038(1) Uani ? ? O5' 0.5477(3) 0.5791(4) 0.1454(2) 0.038(1) Uani ? ? N1 0.3550(3) 0.4483(4) 0.2687(2) 0.031(1) Uani ? ? N3 0.3714(3) 0.4661(4) 0.5144(2) 0.039(1) Uani ? ? C2 0.2824(4) 0.4164(4) 0.3888(3) 0.032(1) Uani ? ? C4 0.4949(4) 0.5694(5) 0.5273(3) 0.039(1) Uani ? ? C5 0.5449(5) 0.6234(5) 0.3892(4) 0.042(1) Uani ? ? C6 0.5312(4) 0.5147(4) 0.2748(3) 0.033(1) Uani ? ? C7 0.6853(4) 0.4080(5) 0.2891(3) 0.042(1) Uani ? ? C8 0.0647(4) 0.4218(6) -0.2002(3) 0.049(1) Uani ? ? C9 -0.0029(6) 0.5546(7) -0.2667(5) 0.072(2) Uani ? ? C10 -0.0259(6) 0.2950(6) -0.2660(4) 0.072(2) Uani ? ? C1' 0.2820(4) 0.3819(5) 0.1354(3) 0.035(1) Uani ? ? C2' 0.2063(4) 0.4811(5) 0.0185(3) 0.041(1) Uani ? ? C3' 0.3408(4) 0.4793(4) -0.0911(3) 0.036(1) Uani ? ? C4' 0.4930(4) 0.3938(5) -0.0210(3) 0.035(1) Uani ? ? C5' 0.6343(4) 0.4834(5) 0.0600(3) 0.041(1) Uani ? ? H3 0.3437 0.4244 0.5996 0.047 Uiso calc N3 H7 0.6607 0.3003 0.3357 0.050 Uiso ? ? H8 0.9393 0.4039 0.3690 0.085 Uiso ? ? H1' 0.1904 0.3206 0.1553 0.042 Uiso calc C1' H2' 0.1856 0.5707 0.0529 0.050 Uiso calc C2' H3' 0.3772 0.5690 -0.1152 0.044 Uiso calc C3' H4' 0.5439 0.3402 -0.0896 0.043 Uiso calc C4' H5' 0.6995 0.5316 -0.0043 0.051 Uiso calc C5' H5a 0.4677 0.6972 0.3591 0.050 Uiso calc C5 H5b 0.6639 0.6559 0.4031 0.050 Uiso calc C5 H9a 0.0510 0.6296 -0.2142 0.086 Uiso calc C9 H9b 0.0259 0.5589 -0.3614 0.086 Uiso calc C9 H9c -0.1282 0.5592 -0.2664 0.086 Uiso calc C9 H10a 0.0243 0.2155 -0.2197 0.086 Uiso calc C10 H10b -0.0097 0.2914 -0.3637 0.086 Uiso calc C10 H10c -0.1494 0.2988 -0.2561 0.086 Uiso calc C10 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 O2 0.035(1) -0.010(1) 0.010(1) 0.062(2) -0.001(1) 0.032(1) O4 0.063(2) -0.021(2) 0.008(1) 0.091(2) -0.024(1) 0.034(1) O7 0.038(1) 0.019(1) 0.008(1) 0.084(2) -0.003(1) 0.033(1) O8 0.050(1) 0.012(2) -0.005(1) 0.109(3) -0.017(2) 0.051(1) O2' 0.038(1) -0.004(2) 0.0025(9) 0.130(3) -0.003(2) 0.025(1) O3' 0.041(1) -0.000(1) 0.0044(8) 0.056(1) -0.001(1) 0.022(1) O4' 0.053(1) 0.003(1) 0.011(1) 0.036(1) 0.001(1) 0.027(1) O5' 0.048(1) -0.004(1) 0.010(1) 0.039(1) 0.002(1) 0.028(1) N1 0.033(1) -0.003(1) 0.006(1) 0.040(2) -0.000(1) 0.021(1) N3 0.044(1) -0.007(1) 0.006(1) 0.053(2) -0.002(1) 0.020(1) C2 0.032(2) 0.006(2) 0.003(1) 0.040(2) -0.001(1) 0.024(1) C4 0.036(2) 0.001(2) 0.006(1) 0.048(2) -0.009(2) 0.033(2) C5 0.042(2) -0.005(2) 0.008(1) 0.044(2) -0.007(2) 0.040(2) C6 0.039(2) -0.004(1) 0.007(1) 0.038(2) -0.002(1) 0.023(1) C7 0.038(2) 0.008(2) 0.001(1) 0.057(2) -0.001(2) 0.029(1) C8 0.045(2) 0.000(2) 0.005(1) 0.079(3) 0.001(2) 0.024(1) C9 0.069(3) 0.028(3) -0.005(2) 0.098(4) 0.001(2) 0.047(2) C10 0.065(3) -0.030(3) 0.004(2) 0.104(4) 0.002(2) 0.045(2) C1' 0.039(2) -0.006(1) 0.006(1) 0.042(2) -0.002(1) 0.025(1) C2' 0.038(2) 0.010(2) 0.005(1) 0.059(2) -0.003(2) 0.026(1) C3' 0.044(2) 0.003(2) 0.006(1) 0.041(2) 0.001(1) 0.024(1) C4' 0.044(2) 0.005(2) 0.010(1) 0.042(2) -0.002(1) 0.022(1) C5' 0.039(2) 0.003(2) 0.014(1) 0.056(2) -0.001(2) 0.031(2) loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 2 -1 0 3 -2 -1 2 -1 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 C7 O7 C5' 109.3(2) yes C8 O2' C2' 108.5(2) yes C8 O3' C3' 107.2(2) yes C1' O4' C4' 108.3(2) yes C6 O5' C5' 107.2(2) yes C2 N1 C6 121.0(2) yes C2 N1 C1' 118.3(2) yes C6 N1 C1' 118.5(2) yes C2 N3 C4 126.4(3) yes O2 C2 N1 124.4(3) yes O2 C2 N3 119.5(2) yes N1 C2 N3 116.1(3) yes O4 C4 N3 121.6(3) yes O4 C4 C5 123.9(3) yes N3 C4 C5 114.5(3) yes C4 C5 C6 112.3(3) yes O5' C6 N1 109.2(2) yes O5' C6 C5 108.2(3) yes O5' C6 C7 103.7(2) yes N1 C6 C5 109.0(2) yes N1 C6 C7 112.1(3) yes C5 C6 C7 114.4(3) yes O7 C7 O8 110.2(3) yes O7 C7 C6 104.5(2) yes O8 C7 C6 109.2(3) yes O2' C8 O3' 103.8(2) yes O2' C8 C9 111.6(3) yes O2' C8 C10 108.5(3) yes O3' C8 C9 110.5(3) yes O3' C8 C10 107.7(3) yes C9 C8 C10 114.2(3) yes O4' C1' N1 110.8(2) yes O4' C1' C2' 105.4(2) yes N1 C1' C2' 114.9(3) yes O2' C2' C1' 107.7(3) yes O2' C2' C3' 104.3(2) yes C1' C2' C3' 105.2(2) yes O3' C3' C2' 104.1(2) yes O3' C3' C4' 110.5(3) yes C2' C3' C4' 103.7(2) yes O4' C4' C3' 105.0(3) yes O4' C4' C5' 109.4(2) yes C3' C4' C5' 111.4(3) yes O7 C5' O5' 105.6(2) yes O7 C5' C4' 112.2(3) yes O5' C5' C4' 108.5(3) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O2 C2 1.225(4) yes O4 C4 1.216(4) yes O7 C7 1.416(4) yes O7 C5' 1.391(4) yes O8 C7 1.370(4) yes O2' C8 1.414(4) yes O2' C2' 1.424(4) yes O3' C8 1.429(4) yes O3' C3' 1.426(4) yes O4' C1' 1.406(4) yes O4' C4' 1.434(4) yes O5' C6 1.399(4) yes O5' C5' 1.440(4) yes N1 C2 1.356(4) yes N1 C6 1.478(4) yes N1 C1' 1.474(4) yes N3 C2 1.392(4) yes N3 C4 1.370(5) yes C4 C5 1.501(5) yes C5 C6 1.513(4) yes C6 C7 1.557(5) yes C8 C9 1.504(7) yes C8 C10 1.514(6) yes C1' C2' 1.536(5) yes C2' C3' 1.535(4) yes C3' C4' 1.515(5) yes C4' C5' 1.523(5) yes 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 O2 C2 N1 C6 -170.9(3) O2 C2 N1 C1' -8.0(5) O2 C2 N3 C4 -163.3(3) O4 C4 N3 C2 172.2(3) O4 C4 C5 C6 152.7(4) O7 C7 C6 O5' -10.4(3) O7 C7 C6 N1 107.3(3) O7 C7 C6 C5 -128.0(3) O7 C5' O5' C6 -32.6(3) O7 C5' C4' O4' 48.3(3) O7 C5' C4' C3' 164.0(2) O8 C7 O7 C5' -126.6(3) O8 C7 C6 O5' 107.5(3) O8 C7 C6 N1 -134.8(3) O8 C7 C6 C5 -10.2(4) O2' C8 O3' C3' -35.1(4) O2' C2' C1' O4' 96.1(3) O2' C2' C1' N1 -141.7(2) O2' C2' C3' O3' -4.2(3) O2' C2' C3' C4' -119.9(3) O3' C8 O2' C2' 32.4(4) O3' C3' C2' C1' 109.0(3) O3' C3' C4' O4' -85.6(3) O3' C3' C4' C5' 156.0(2) O4' C1' N1 C2 -120.7(3) O4' C1' N1 C6 42.7(4) O4' C1' C2' C3' -14.7(3) O4' C4' C3' C2' 25.5(3) O4' C4' C5' O5' -68.1(3) O5' C6 N1 C2 -159.3(3) O5' C6 N1 C1' 37.9(4) O5' C6 C5 C4 169.2(3) O5' C5' O7 C7 25.4(4) O5' C5' C4' C3' 47.6(3) N1 C2 N3 C4 17.4(5) N1 C6 O5' C5' -93.9(3) N1 C6 C5 C4 50.6(4) N1 C1' O4' C4' -92.6(3) N1 C1' C2' C3' 107.5(3) N3 C2 N1 C6 8.3(4) N3 C2 N1 C1' 171.2(3) N3 C4 C5 C6 -30.2(4) C2 N1 C6 C5 -41.2(4) C2 N1 C6 C7 86.4(3) C2 N1 C1' C2' 120.1(3) C2 N3 C4 C5 -5.0(5) C4 C5 C6 C7 -75.7(4) C5 C6 O5' C5' 147.6(3) C5 C6 N1 C1' 155.9(3) C6 O5' C5' C4' 87.9(3) C6 N1 C1' C2' -76.6(3) C6 C7 O7 C5' -9.4(4) C7 O7 C5' C4' -92.7(3) C7 C6 O5' C5' 25.7(3) C7 C6 N1 C1' -76.5(3) C8 O2' C2' C1' -128.7(3) C8 O2' C2' C3' -17.4(4) C8 O3' C3' C2' 24.0(3) C8 O3' C3' C4' 134.8(3) C9 C8 O2' C2' -86.6(4) C9 C8 O3' C3' 84.7(3) C10 C8 O2' C2' 146.7(3) C10 C8 O3' C3' -150.0(3) C1' O4' C4' C3' -37.0(3) C1' O4' C4' C5' 82.7(3) C1' C2' C3' C4' -6.7(3) C2' C1' O4' C4' 32.2(3) C2' C3' C4' C5' -92.9(3)