#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/31/2013145.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_2013145 loop_ _publ_author_name 'Tsao, Jonglin F.' 'Faruqi, Sana R.' 'Thompson, Hugh W.' 'Lalancette, Roger A.' _publ_section_title ; Two new heterocyclic [3.3.3.0^1,5^]-propellanoid compounds: 2,8-dioxatricyclo[3.3.3.0^1,5^]undecane-3,7-dione and a related dimer ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o57 _journal_page_last o59 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety 'C18 H22 O7' _chemical_formula_sum 'C18 H22 O7' _chemical_formula_weight 350.36 _chemical_melting_point 465 _chemical_name_systematic ; 7,7'-Oxybis(2,8-dioxatricyclo[3.3.3.0^1,5^]undecan-3-one) ; _space_group_IT_number 43 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'F 2 -2d' _symmetry_space_group_name_H-M 'F d d 2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 11.571(5) _cell_length_b 27.069(10) _cell_length_c 10.754(5) _cell_measurement_reflns_used 20 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 6.2 _cell_measurement_theta_min 2.7 _cell_volume 3368(2) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_data_reduction XSCANS _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method 2\q/\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 0.061 _diffrn_reflns_av_sigmaI/netI 0.084 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 1578 _diffrn_reflns_theta_full 24.99 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_theta_min 2.69 _diffrn_standards_decay_% 'variation <1.6' _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details '(SHELXTL; Sheldrick, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description parallelepiped _exptl_crystal_F_000 1488 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.11 _refine_diff_density_min -0.13 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.00 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 114 _refine_ls_number_reflns 789 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.00 _refine_ls_R_factor_all 0.105 _refine_ls_R_factor_gt 0.050 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.00 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0143P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.070 _refine_ls_wR_factor_ref 0.082 _reflns_number_gt 463 _reflns_number_total 789 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file fr1401.cif _[local]_cod_data_source_block II _cod_database_code 2013145 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' 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 O2 0.6380(3) 0.35079(12) 0.5720(3) 0.0636(10) Uani d . 1 . . O O3 0.7379(3) 0.36642(13) 0.7441(4) 0.0851(13) Uani d . 1 . . O O7 0.7500 0.2500 0.5725(4) 0.0586(13) Uani d S 1 . . O O8 0.6108(3) 0.28387(14) 0.4388(3) 0.0679(11) Uani d . 1 . . O C1 0.5562(5) 0.31514(18) 0.5266(5) 0.0539(13) Uani d . 1 . . C C3 0.6640(5) 0.34280(19) 0.6933(5) 0.0582(15) Uani d . 1 . . C C4 0.5898(4) 0.30279(16) 0.7460(4) 0.0560(13) Uani d . 1 . . C C5 0.5182(4) 0.28239(17) 0.6385(5) 0.0517(13) Uani d . 1 . . C C6 0.5524(5) 0.23048(18) 0.5958(5) 0.0632(16) Uani d . 1 . . C C7 0.6472(5) 0.24046(18) 0.5046(6) 0.0662(15) Uani d . 1 . . C C9 0.4486(4) 0.3397(2) 0.4729(6) 0.0738(18) Uani d . 1 . . C C10 0.3504(5) 0.3049(2) 0.5156(6) 0.0795(18) Uani d . 1 . . C C11 0.3872(5) 0.2900(2) 0.6461(5) 0.0710(17) Uani d . 1 . . C H4A 0.5397 0.3159 0.8104 0.067 Uiso calc R 1 . . H H4B 0.6373 0.2769 0.7820 0.067 Uiso calc R 1 . . H H6A 0.5799 0.2107 0.6650 0.076 Uiso calc R 1 . . H H6B 0.4880 0.2137 0.5565 0.076 Uiso calc R 1 . . H H7B 0.6575 0.2125 0.4477 0.079 Uiso calc R 1 . . H H9A 0.4525 0.3415 0.3830 0.089 Uiso calc R 1 . . H H9B 0.4383 0.3727 0.5063 0.089 Uiso calc R 1 . . H H10A 0.2767 0.3220 0.5169 0.095 Uiso calc R 1 . . H H10B 0.3445 0.2763 0.4616 0.095 Uiso calc R 1 . . H H11A 0.3489 0.2597 0.6712 0.085 Uiso calc R 1 . . H H11B 0.3684 0.3157 0.7055 0.085 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 O2 0.068(2) 0.054(2) 0.069(3) -0.0108(19) -0.014(2) 0.012(2) O3 0.086(3) 0.078(3) 0.092(3) -0.023(2) -0.028(3) -0.014(2) O7 0.059(3) 0.068(3) 0.049(3) 0.008(3) 0.000 0.000 O8 0.075(3) 0.082(3) 0.047(2) 0.011(2) -0.003(2) 0.001(2) C1 0.061(3) 0.050(3) 0.051(3) 0.001(3) -0.012(3) 0.002(3) C3 0.062(4) 0.056(4) 0.057(4) 0.007(3) -0.010(3) -0.006(3) C4 0.066(3) 0.051(3) 0.051(3) -0.003(3) 0.000(3) -0.001(3) C5 0.055(3) 0.045(3) 0.056(3) -0.006(3) 0.001(3) -0.003(3) C6 0.070(4) 0.055(4) 0.065(4) -0.005(3) -0.005(3) -0.002(3) C7 0.085(4) 0.054(3) 0.060(4) 0.012(3) -0.010(4) -0.013(3) C9 0.068(4) 0.075(4) 0.079(5) 0.003(3) -0.017(4) 0.008(3) C10 0.065(4) 0.089(4) 0.085(5) 0.007(3) -0.022(4) -0.015(4) C11 0.067(4) 0.072(4) 0.074(4) -0.007(3) 0.009(4) -0.016(3) 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 O2 C3 . 1.356(6) ? O2 C1 . 1.437(6) ? O3 C3 . 1.199(5) ? O7 C7 . 1.419(5) ? O7 C7 14_655 1.419(5) ? O8 C1 . 1.417(6) ? O8 C7 . 1.435(6) ? C1 C9 . 1.525(6) ? C1 C5 . 1.558(7) ? C3 C4 . 1.494(6) ? C4 C5 . 1.526(6) ? C5 C6 . 1.531(6) ? C5 C11 . 1.531(6) ? C6 C7 . 1.496(7) ? C9 C10 . 1.545(7) ? C10 C11 . 1.521(7) ? C4 H4A . 0.9700 ? C4 H4B . 0.9700 ? C6 H6A . 0.9700 ? C6 H6B . 0.9700 ? C7 H7B . 0.9800 ? C9 H9A . 0.9700 ? C9 H9B . 0.9700 ? C10 H10A . 0.9700 ? C10 H10B . 0.9700 ? C11 H11A . 0.9700 ? C11 H11B . 0.9700 ? 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' 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_site_symmetry_3 _geom_angle C3 O2 C1 . 111.4(4) C7 O7 C7 14_655 118.1(6) C1 O8 C7 . 106.9(4) O8 C1 O2 . 109.5(4) O8 C1 C9 . 111.8(5) O2 C1 C9 . 111.9(4) O8 C1 C5 . 107.5(4) O2 C1 C5 . 107.8(4) C9 C1 C5 . 108.1(4) O3 C3 O2 . 120.8(5) O3 C3 C4 . 128.5(5) O2 C3 C4 . 110.7(5) C3 C4 C5 . 106.6(4) C4 C5 C6 . 114.8(4) C4 C5 C11 . 116.6(5) C6 C5 C11 . 113.3(4) C4 C5 C1 . 103.1(3) C6 C5 C1 . 102.6(4) C11 C5 C1 . 104.1(4) C7 C6 C5 . 102.7(4) O7 C7 O8 . 110.5(4) O7 C7 C6 . 108.1(5) O8 C7 C6 . 104.9(4) C1 C9 C10 . 102.8(4) C11 C10 C9 . 103.3(5) C10 C11 C5 . 105.3(5) C3 C4 H4A . 110.4 C5 C4 H4A . 110.4 C3 C4 H4B . 110.4 C5 C4 H4B . 110.4 H4A C4 H4B . 108.6 C7 C6 H6A . 111.2 C5 C6 H6A . 111.2 C7 C6 H6B . 111.2 C5 C6 H6B . 111.2 H6A C6 H6B . 109.1 O7 C7 H7B . 111.1 O8 C7 H7B . 111.1 C6 C7 H7B . 111.1 C1 C9 H9A . 111.2 C10 C9 H9A . 111.2 C1 C9 H9B . 111.2 C10 C9 H9B . 111.2 H9A C9 H9B . 109.1 C11 C10 H10A . 111.1 C9 C10 H10A . 111.1 C11 C10 H10B . 111.1 C9 C10 H10B . 111.1 H10A C10 H10B . 109.1 C10 C11 H11A . 110.7 C5 C11 H11A . 110.7 C10 C11 H11B . 110.7 C5 C11 H11B . 110.7 H11A C11 H11B . 108.8 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_site_symmetry_1 _geom_torsion C7 O8 C1 O2 . 95.9(5) C7 O8 C1 C9 . -139.5(4) C7 O8 C1 C5 . -21.0(5) C3 O2 C1 O8 . -111.7(4) C3 O2 C1 C9 . 123.7(5) C3 O2 C1 C5 . 5.0(5) C1 O2 C3 O3 . 173.9(5) C1 O2 C3 C4 . -6.2(5) O3 C3 C4 C5 . -175.2(5) O2 C3 C4 C5 . 4.9(5) C3 C4 C5 C6 . 109.0(4) C3 C4 C5 C11 . -115.1(5) C3 C4 C5 C1 . -1.7(5) O8 C1 C5 C4 . 116.3(4) O2 C1 C5 C4 . -1.7(5) C9 C1 C5 C4 . -122.8(5) O8 C1 C5 C6 . -3.3(5) O2 C1 C5 C6 . -121.2(4) C9 C1 C5 C6 . 117.6(5) O8 C1 C5 C11 . -121.5(4) O2 C1 C5 C11 . 120.5(4) C9 C1 C5 C11 . -0.6(5) C4 C5 C6 C7 . -86.2(5) C11 C5 C6 C7 . 136.4(5) C1 C5 C6 C7 . 24.8(5) C7 O7 C7 O8 14_655 -67.0(4) C7 O7 C7 C6 14_655 178.7(4) C1 O8 C7 O7 . -78.4(5) C1 O8 C7 C6 . 37.8(5) C5 C6 C7 O7 . 79.2(5) C5 C6 C7 O8 . -38.7(5) O8 C1 C9 C10 . 95.0(5) O2 C1 C9 C10 . -141.7(5) C5 C1 C9 C10 . -23.1(6) C1 C9 C10 C11 . 38.3(5) C9 C10 C11 C5 . -39.7(5) C4 C5 C11 C10 . 137.6(4) C6 C5 C11 C10 . -85.8(5) C1 C5 C11 C10 . 24.8(5) _cod_database_fobs_code 2013145