#------------------------------------------------------------------------------ #$Date: 2012-02-28 14:14:52 +0200 (Tue, 28 Feb 2012) $ #$Revision: 35911 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/24/1502499.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_1502499 loop_ _publ_author_name 'Qi, Chaorong' 'Jiang, Huanfeng' 'Huang, Liangbin' 'Yuan, Gaoqing' 'Ren, Yanwei' _publ_section_title ; Carbon dioxide triggered and copper-catalyzed domino reaction: efficient construction of highly substituted 3(2H)-furanones from nitriles and propargylic alcohols. ; _journal_issue 20 _journal_name_full 'Organic letters' _journal_page_first 5520 _journal_page_last 5523 _journal_volume 13 _journal_year 2011 _chemical_formula_moiety 'C18 H20 O4' _chemical_formula_sum 'C18 H20 O4' _chemical_formula_weight 300.34 _chemical_name_systematic ; ? ; _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 71.59(3) _cell_angle_beta 75.66(3) _cell_angle_gamma 81.70(3) _cell_formula_units_Z 2 _cell_length_a 6.7081(13) _cell_length_b 11.086(2) _cell_length_c 11.437(2) _cell_measurement_reflns_used 2895 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.89 _cell_measurement_theta_min 2.35 _cell_volume 779.8(3) _computing_cell_refinement RAPID-AUTO _computing_data_collection 'RAPID-AUTO (Rigaku, 1998)' _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2002)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Rigaku/MSC Mercury CCD' _diffrn_measurement_method \w _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 6299 _diffrn_reflns_theta_full 25.20 _diffrn_reflns_theta_max 25.20 _diffrn_reflns_theta_min 3.11 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_correction_T_min 0.985 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Jacobson, 1998)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 320 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.17 _refine_diff_density_max 0.289 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.066 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 201 _refine_ls_number_reflns 2802 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.120 _refine_ls_R_factor_all 0.1100 _refine_ls_R_factor_gt 0.0570 _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^)+(0.1403P)^2^+0.1956P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1631 _refine_ls_wR_factor_ref 0.2609 _reflns_number_gt 1514 _reflns_number_total 2802 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file ol202241r_si_002.cif _[local]_cod_data_source_block shelxl _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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_original_cell_volume 779.8(2) _cod_database_code 1502499 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 O1 O -0.5329(4) 0.4162(3) 0.4055(2) 0.0763(8) Uani 1 1 d . O2 O -0.4469(4) 0.5553(3) 0.2162(3) 0.0897(10) Uani 1 1 d . O3 O 0.6936(3) 0.0932(2) 0.1434(2) 0.0608(7) Uani 1 1 d . O4 O 0.2834(4) -0.0376(2) 0.3887(3) 0.0785(9) Uani 1 1 d . C1 C 0.9230(7) -0.2269(4) 0.2088(5) 0.0879(13) Uani 1 1 d . H1A H 1.0567 -0.2584 0.1690 0.105 Uiso 1 1 calc R H1B H 0.8558 -0.2988 0.2723 0.105 Uiso 1 1 calc R C2 C 0.9523(6) -0.1305(4) 0.2719(4) 0.0816(12) Uani 1 1 d . H2A H 1.0306 -0.1718 0.3365 0.098 Uiso 1 1 calc R H2B H 1.0304 -0.0624 0.2097 0.098 Uiso 1 1 calc R C3 C 0.7458(6) -0.0748(4) 0.3312(4) 0.0665(10) Uani 1 1 d . H3A H 0.6772 -0.1409 0.4018 0.080 Uiso 1 1 calc R H3B H 0.7695 -0.0083 0.3635 0.080 Uiso 1 1 calc R C4 C 0.6073(5) -0.0200(3) 0.2387(3) 0.0557(9) Uani 1 1 d . C5 C 0.5846(6) -0.1151(3) 0.1713(4) 0.0649(10) Uani 1 1 d . H5A H 0.5074 -0.1848 0.2314 0.078 Uiso 1 1 calc R H5B H 0.5075 -0.0731 0.1063 0.078 Uiso 1 1 calc R C6 C 0.7951(7) -0.1685(4) 0.1114(4) 0.0789(12) Uani 1 1 d . H6A H 0.7757 -0.2324 0.0745 0.095 Uiso 1 1 calc R H6B H 0.8666 -0.1005 0.0447 0.095 Uiso 1 1 calc R C7 C -0.7368(6) 0.4804(4) 0.4206(4) 0.0848(13) Uani 1 1 d . H7A H -0.7271 0.5666 0.4187 0.127 Uiso 1 1 calc R H7B H -0.8203 0.4366 0.5000 0.127 Uiso 1 1 calc R H7C H -0.7986 0.4806 0.3533 0.127 Uiso 1 1 calc R C8 C -0.4009(6) 0.4626(3) 0.2976(3) 0.0586(9) Uani 1 1 d . C9 C -0.1997(5) 0.3890(3) 0.2862(3) 0.0533(8) Uani 1 1 d . C10 C -0.0473(5) 0.4294(3) 0.1791(3) 0.0623(9) Uani 1 1 d . H10 H -0.0704 0.5058 0.1186 0.075 Uiso 1 1 calc R C11 C 0.1370(6) 0.3593(3) 0.1602(3) 0.0606(9) Uani 1 1 d . H11 H 0.2359 0.3884 0.0868 0.073 Uiso 1 1 calc R C12 C 0.1786(5) 0.2454(3) 0.2489(3) 0.0510(8) Uani 1 1 d . C13 C 0.0269(6) 0.2068(3) 0.3581(3) 0.0611(9) Uani 1 1 d . H13 H 0.0512 0.1320 0.4203 0.073 Uiso 1 1 calc R C14 C -0.1601(5) 0.2781(3) 0.3759(3) 0.0601(9) Uani 1 1 d . H14 H -0.2596 0.2502 0.4494 0.072 Uiso 1 1 calc R C15 C 0.6230(6) 0.3116(3) 0.0490(4) 0.0660(10) Uani 1 1 d . H15A H 0.7704 0.3097 0.0347 0.099 Uiso 1 1 calc R H15B H 0.5617 0.3826 0.0798 0.099 Uiso 1 1 calc R H15C H 0.5839 0.3204 -0.0287 0.099 Uiso 1 1 calc R C16 C 0.5505(5) 0.1921(3) 0.1431(3) 0.0523(8) Uani 1 1 d . C17 C 0.3696(5) 0.1635(3) 0.2293(3) 0.0519(8) Uani 1 1 d . C18 C 0.3981(5) 0.0297(3) 0.2983(3) 0.0569(9) 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 O1 0.0582(15) 0.0898(18) 0.0654(17) -0.0169(14) -0.0037(13) 0.0138(13) O2 0.080(2) 0.0801(19) 0.084(2) -0.0009(17) -0.0158(17) 0.0185(16) O3 0.0561(14) 0.0581(14) 0.0572(14) -0.0096(11) -0.0022(11) -0.0032(11) O4 0.0720(17) 0.0620(15) 0.0723(18) 0.0025(14) 0.0058(14) 0.0000(13) C1 0.082(3) 0.082(3) 0.089(3) -0.028(3) -0.010(3) 0.021(2) C2 0.064(2) 0.097(3) 0.078(3) -0.020(2) -0.022(2) 0.013(2) C3 0.069(2) 0.069(2) 0.061(2) -0.0180(18) -0.0199(19) 0.0078(18) C4 0.057(2) 0.0507(18) 0.0487(19) -0.0066(15) -0.0037(15) -0.0003(15) C5 0.074(2) 0.060(2) 0.061(2) -0.0169(18) -0.0173(19) -0.0046(18) C6 0.093(3) 0.074(3) 0.068(3) -0.029(2) -0.008(2) 0.001(2) C7 0.058(2) 0.104(3) 0.089(3) -0.035(3) -0.012(2) 0.018(2) C8 0.059(2) 0.060(2) 0.055(2) -0.0159(17) -0.0120(17) -0.0017(17) C9 0.0520(19) 0.0556(18) 0.0486(18) -0.0125(15) -0.0105(15) 0.0010(15) C10 0.062(2) 0.060(2) 0.056(2) -0.0065(17) -0.0123(17) 0.0019(17) C11 0.062(2) 0.0585(19) 0.0484(19) -0.0024(16) -0.0053(16) -0.0041(16) C12 0.0495(18) 0.0551(18) 0.0449(18) -0.0118(15) -0.0075(15) -0.0035(14) C13 0.064(2) 0.0550(19) 0.0504(19) -0.0057(16) -0.0036(17) 0.0023(16) C14 0.059(2) 0.0599(19) 0.0480(19) -0.0056(16) -0.0018(16) -0.0010(16) C15 0.063(2) 0.058(2) 0.065(2) -0.0056(18) -0.0047(18) -0.0101(17) C16 0.0498(19) 0.0523(18) 0.0487(18) -0.0127(15) -0.0034(15) -0.0013(14) C17 0.0543(19) 0.0498(17) 0.0447(17) -0.0085(14) -0.0059(15) -0.0021(14) C18 0.055(2) 0.0572(19) 0.0490(19) -0.0072(16) -0.0030(16) -0.0057(15) 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 C8 O1 C7 116.8(3) C16 O3 C4 108.4(2) C6 C1 C2 111.3(3) C6 C1 H1A 109.4 C2 C1 H1A 109.4 C6 C1 H1B 109.4 C2 C1 H1B 109.4 H1A C1 H1B 108.0 C3 C2 C1 111.2(3) C3 C2 H2A 109.4 C1 C2 H2A 109.4 C3 C2 H2B 109.4 C1 C2 H2B 109.4 H2A C2 H2B 108.0 C4 C3 C2 112.4(3) C4 C3 H3A 109.1 C2 C3 H3A 109.1 C4 C3 H3B 109.1 C2 C3 H3B 109.1 H3A C3 H3B 107.9 O3 C4 C3 109.4(3) O3 C4 C18 103.5(2) C3 C4 C18 112.7(3) O3 C4 C5 108.2(3) C3 C4 C5 112.1(3) C18 C4 C5 110.5(3) C6 C5 C4 111.6(3) C6 C5 H5A 109.3 C4 C5 H5A 109.3 C6 C5 H5B 109.3 C4 C5 H5B 109.3 H5A C5 H5B 108.0 C1 C6 C5 110.4(3) C1 C6 H6A 109.6 C5 C6 H6A 109.6 C1 C6 H6B 109.6 C5 C6 H6B 109.6 H6A C6 H6B 108.1 O1 C7 H7A 109.5 O1 C7 H7B 109.5 H7A C7 H7B 109.5 O1 C7 H7C 109.5 H7A C7 H7C 109.5 H7B C7 H7C 109.5 O2 C8 O1 122.0(3) O2 C8 C9 124.2(3) O1 C8 C9 113.8(3) C14 C9 C10 118.4(3) C14 C9 C8 122.3(3) C10 C9 C8 119.3(3) C11 C10 C9 121.4(3) C11 C10 H10 119.3 C9 C10 H10 119.3 C10 C11 C12 121.1(3) C10 C11 H11 119.4 C12 C11 H11 119.4 C11 C12 C13 117.3(3) C11 C12 C17 122.9(3) C13 C12 C17 119.7(3) C14 C13 C12 121.1(3) C14 C13 H13 119.4 C12 C13 H13 119.4 C9 C14 C13 120.7(3) C9 C14 H14 119.7 C13 C14 H14 119.7 C16 C15 H15A 109.5 C16 C15 H15B 109.5 H15A C15 H15B 109.5 C16 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 O3 C16 C17 114.8(3) O3 C16 C15 112.6(3) C17 C16 C15 132.6(3) C16 C17 C18 105.7(3) C16 C17 C12 129.1(3) C18 C17 C12 125.2(3) O4 C18 C17 130.1(3) O4 C18 C4 122.5(3) C17 C18 C4 107.4(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C8 1.326(4) O1 C7 1.445(4) O2 C8 1.210(4) O3 C16 1.348(4) O3 C4 1.460(4) O4 C18 1.225(4) C1 C6 1.501(6) C1 C2 1.523(6) C1 H1A 0.9700 C1 H1B 0.9700 C2 C3 1.521(5) C2 H2A 0.9700 C2 H2B 0.9700 C3 C4 1.506(5) C3 H3A 0.9700 C3 H3B 0.9700 C4 C18 1.510(4) C4 C5 1.532(5) C5 C6 1.533(5) C5 H5A 0.9700 C5 H5B 0.9700 C6 H6A 0.9700 C6 H6B 0.9700 C7 H7A 0.9600 C7 H7B 0.9600 C7 H7C 0.9600 C8 C9 1.472(5) C9 C14 1.371(5) C9 C10 1.383(5) C10 C11 1.369(5) C10 H10 0.9300 C11 C12 1.390(5) C11 H11 0.9300 C12 C13 1.392(5) C12 C17 1.471(5) C13 C14 1.389(5) C13 H13 0.9300 C14 H14 0.9300 C15 C16 1.475(4) C15 H15A 0.9600 C15 H15B 0.9600 C15 H15C 0.9600 C16 C17 1.366(4) C17 C18 1.453(5)