#------------------------------------------------------------------------------ #$Date: 2012-02-24 19:13:23 +0200 (Fri, 24 Feb 2012) $ #$Revision: 34330 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/02/57/4025765.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4025765 loop_ _publ_author_name 'Tyrone C. Casey' 'Julie Carlisle' 'Patrizia Tisselli' 'Louise Male' 'Neil Spencer' 'Richard S. Grainger' _publ_contact_author_address ; School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT, UK. ; _publ_contact_author_email r.s.grainger@bham.ac.uk _publ_contact_author_fax '0121 414 4403' _publ_contact_author_name 'Richard S. Grainger' _publ_contact_author_phone '0121 414 4465' _publ_section_title ; Stereoselective \a,\a'-Annelation Reactions of 1,3-Dioxan-5-ones ; _journal_name_full 'Journal of Organic Chemistry' _journal_page_first 7461 _journal_page_last 7464 _journal_volume 75 _journal_year 2010 _chemical_formula_moiety 'C11 H16 O5' _chemical_formula_sum 'C11 H16 O5' _chemical_formula_weight 228.24 _chemical_name_systematic ; Methyl 3,3-Dimethyl-9-oxo-2,4-dioxabicyclo[3.3.1]nonane-7\a-carboxylate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 108.7380(10) _cell_angle_beta 107.450(2) _cell_angle_gamma 94.121(2) _cell_formula_units_Z 2 _cell_length_a 7.9524(2) _cell_length_b 8.2007(2) _cell_length_c 9.4468(2) _cell_measurement_reflns_used 9863 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.91 _cell_volume 546.84(2) _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution ; SIR92, (Altomare, Cascarano, Giacovazzo, Guagliardi, Burla, Polidori & Camalli, 1994) ; _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 13210 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 3.74 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_T_max 0.9913 _exptl_absorpt_correction_T_min 0.9891 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 244 _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.334 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.048 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 148 _refine_ls_number_reflns 2497 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.063 _refine_ls_R_factor_all 0.0462 _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^)+(0.0311P)^2^+0.2891P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0871 _refine_ls_wR_factor_ref 0.0933 _reflns_number_gt 2185 _reflns_number_total 2497 _reflns_threshold_expression >2\s(I) _[local]_cod_data_source_file jo101531b_si_001.cif _[local]_cod_data_source_block 5a _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to the built-in table from CIF Core dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to the built-in table from CIF Core dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana ; _cod_database_code 4025765 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.42350(16) 0.31305(16) 0.60677(15) 0.0175(3) Uani 1 1 d . . . C2 C 0.48157(16) 0.37688(16) 0.78602(14) 0.0165(2) Uani 1 1 d . . . H2 H 0.5837 0.4789 0.8372 0.020 Uiso 1 1 calc R . . C3 C 0.53678(16) 0.21584(16) 0.82435(15) 0.0179(3) Uani 1 1 d . . . H3A H 0.5841 0.2465 0.9411 0.022 Uiso 1 1 calc R . . H3B H 0.6329 0.1783 0.7817 0.022 Uiso 1 1 calc R . . C4 C 0.37332(16) 0.06480(16) 0.74982(15) 0.0177(3) Uani 1 1 d . . . H4 H 0.4235 -0.0433 0.7511 0.021 Uiso 1 1 calc R . . C5 C 0.27054(17) 0.03104(16) 0.57344(15) 0.0190(3) Uani 1 1 d . . . H5A H 0.1520 -0.0431 0.5420 0.023 Uiso 1 1 calc R . . H5B H 0.3372 -0.0363 0.5086 0.023 Uiso 1 1 calc R . . C6 C 0.24090(16) 0.19724(16) 0.53266(14) 0.0180(3) Uani 1 1 d . . . H6 H 0.2000 0.1651 0.4146 0.022 Uiso 1 1 calc R . . C7 C 0.18049(16) 0.43815(16) 0.72809(14) 0.0177(3) Uani 1 1 d . . . C8 C 0.25051(17) 0.08158(16) 0.84790(15) 0.0185(3) Uani 1 1 d . . . C9 C 0.23976(19) 0.1552(2) 1.10758(16) 0.0266(3) Uani 1 1 d . . . H9A H 0.3184 0.2094 1.2189 0.040 Uiso 1 1 calc R . . H9B H 0.1797 0.0377 1.0888 0.040 Uiso 1 1 calc R . . H9C H 0.1496 0.2272 1.0845 0.040 Uiso 1 1 calc R . . C10 C 0.22510(18) 0.59385(17) 0.68220(16) 0.0223(3) Uani 1 1 d . . . H10A H 0.3081 0.5681 0.6228 0.033 Uiso 1 1 calc R . . H10B H 0.2812 0.6981 0.7786 0.033 Uiso 1 1 calc R . . H10C H 0.1147 0.6154 0.6156 0.033 Uiso 1 1 calc R . . C11 C 0.03795(18) 0.46139(18) 0.80497(17) 0.0242(3) Uani 1 1 d . . . H11A H -0.0739 0.4681 0.7289 0.036 Uiso 1 1 calc R . . H11B H 0.0777 0.5697 0.8988 0.036 Uiso 1 1 calc R . . H11C H 0.0176 0.3614 0.8371 0.036 Uiso 1 1 calc R . . O1 O 0.52390(12) 0.32701(13) 0.53478(11) 0.0235(2) Uani 1 1 d . . . O2 O 0.33375(11) 0.41555(11) 0.84120(10) 0.0174(2) Uani 1 1 d . . . O3 O 0.11060(11) 0.27989(11) 0.59267(10) 0.0193(2) Uani 1 1 d . . . O4 O 0.08968(12) 0.03571(13) 0.79538(11) 0.0257(2) Uani 1 1 d . . . O5 O 0.34520(12) 0.14222(13) 1.00513(11) 0.0221(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0205(6) 0.0157(6) 0.0192(6) 0.0080(5) 0.0085(5) 0.0052(5) C2 0.0143(6) 0.0171(6) 0.0176(6) 0.0057(5) 0.0056(5) 0.0012(4) C3 0.0160(6) 0.0190(6) 0.0188(6) 0.0071(5) 0.0057(5) 0.0034(5) C4 0.0190(6) 0.0151(6) 0.0210(6) 0.0075(5) 0.0083(5) 0.0041(5) C5 0.0190(6) 0.0168(6) 0.0184(6) 0.0022(5) 0.0073(5) 0.0016(5) C6 0.0189(6) 0.0202(6) 0.0140(5) 0.0044(5) 0.0063(5) 0.0030(5) C7 0.0174(6) 0.0178(6) 0.0164(6) 0.0056(5) 0.0040(5) 0.0039(5) C8 0.0221(6) 0.0151(6) 0.0210(6) 0.0086(5) 0.0087(5) 0.0034(5) C9 0.0283(7) 0.0353(8) 0.0236(7) 0.0147(6) 0.0141(6) 0.0089(6) C10 0.0258(7) 0.0187(6) 0.0231(6) 0.0099(5) 0.0068(5) 0.0048(5) C11 0.0244(7) 0.0261(7) 0.0261(7) 0.0096(5) 0.0128(5) 0.0090(5) O1 0.0247(5) 0.0280(5) 0.0245(5) 0.0128(4) 0.0140(4) 0.0050(4) O2 0.0179(4) 0.0204(4) 0.0155(4) 0.0074(3) 0.0066(3) 0.0057(3) O3 0.0161(4) 0.0184(4) 0.0196(4) 0.0031(3) 0.0051(3) 0.0023(3) O4 0.0204(5) 0.0293(5) 0.0270(5) 0.0100(4) 0.0089(4) -0.0010(4) O5 0.0217(5) 0.0295(5) 0.0190(4) 0.0116(4) 0.0091(4) 0.0055(4) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C6 124.51(11) . . ? O1 C1 C2 123.62(11) . . ? C6 C1 C2 110.56(10) . . ? O2 C2 C1 111.72(9) . . ? O2 C2 C3 106.40(9) . . ? C1 C2 C3 103.36(10) . . ? O2 C2 H2 111.7 . . ? C1 C2 H2 111.7 . . ? C3 C2 H2 111.7 . . ? C2 C3 C4 109.85(10) . . ? C2 C3 H3A 109.7 . . ? C4 C3 H3A 109.7 . . ? C2 C3 H3B 109.7 . . ? C4 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? C8 C4 C5 112.58(10) . . ? C8 C4 C3 113.29(10) . . ? C5 C4 C3 113.09(10) . . ? C8 C4 H4 105.7 . . ? C5 C4 H4 105.7 . . ? C3 C4 H4 105.7 . . ? C4 C5 C6 115.23(10) . . ? C4 C5 H5A 108.5 . . ? C6 C5 H5A 108.5 . . ? C4 C5 H5B 108.5 . . ? C6 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? O3 C6 C1 112.27(10) . . ? O3 C6 C5 111.65(10) . . ? C1 C6 C5 104.55(10) . . ? O3 C6 H6 109.4 . . ? C1 C6 H6 109.4 . . ? C5 C6 H6 109.4 . . ? O3 C7 O2 109.58(10) . . ? O3 C7 C11 105.53(10) . . ? O2 C7 C11 106.05(10) . . ? O3 C7 C10 111.80(10) . . ? O2 C7 C10 111.37(10) . . ? C11 C7 C10 112.18(11) . . ? O4 C8 O5 122.76(12) . . ? O4 C8 C4 125.63(12) . . ? O5 C8 C4 111.41(10) . . ? O5 C9 H9A 109.5 . . ? O5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 C11 H11A 109.5 . . ? C7 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C7 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C7 O2 C2 115.03(9) . . ? C7 O3 C6 115.67(9) . . ? C8 O5 C9 115.31(10) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.2147(15) . ? C1 C6 1.5052(17) . ? C1 C2 1.5105(17) . ? C2 O2 1.4385(14) . ? C2 C3 1.5373(17) . ? C2 H2 1.0000 . ? C3 C4 1.5424(17) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C8 1.5203(17) . ? C4 C5 1.5412(17) . ? C4 H4 1.0000 . ? C5 C6 1.5462(18) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 O3 1.4355(14) . ? C6 H6 1.0000 . ? C7 O3 1.4258(15) . ? C7 O2 1.4284(15) . ? C7 C11 1.5115(17) . ? C7 C10 1.5254(17) . ? C8 O4 1.2058(16) . ? C8 O5 1.3496(15) . ? C9 O5 1.4438(15) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 O2 154.67(11) . . . . ? C6 C1 C2 O2 -37.92(13) . . . . ? O1 C1 C2 C3 -91.32(14) . . . . ? C6 C1 C2 C3 76.10(12) . . . . ? O2 C2 C3 C4 55.29(12) . . . . ? C1 C2 C3 C4 -62.51(12) . . . . ? C2 C3 C4 C8 -80.75(12) . . . . ? C2 C3 C4 C5 48.90(13) . . . . ? C8 C4 C5 C6 86.86(13) . . . . ? C3 C4 C5 C6 -43.15(14) . . . . ? O1 C1 C6 O3 -139.49(12) . . . . ? C2 C1 C6 O3 53.22(13) . . . . ? O1 C1 C6 C5 99.30(14) . . . . ? C2 C1 C6 C5 -67.98(12) . . . . ? C4 C5 C6 O3 -71.85(13) . . . . ? C4 C5 C6 C1 49.76(13) . . . . ? C5 C4 C8 O4 16.34(17) . . . . ? C3 C4 C8 O4 146.25(13) . . . . ? C5 C4 C8 O5 -168.76(10) . . . . ? C3 C4 C8 O5 -38.86(14) . . . . ? O3 C7 O2 C2 61.73(12) . . . . ? C11 C7 O2 C2 175.19(9) . . . . ? C10 C7 O2 C2 -62.51(13) . . . . ? C1 C2 O2 C7 -17.92(13) . . . . ? C3 C2 O2 C7 -130.04(10) . . . . ? O2 C7 O3 C6 -45.17(13) . . . . ? C11 C7 O3 C6 -158.96(10) . . . . ? C10 C7 O3 C6 78.81(13) . . . . ? C1 C6 O3 C7 -10.82(14) . . . . ? C5 C6 O3 C7 106.21(11) . . . . ? O4 C8 O5 C9 -2.34(18) . . . . ? C4 C8 O5 C9 -177.40(10) . . . . ?