#------------------------------------------------------------------------------ #$Date: 2014-12-24 13:18:19 +0200 (Wed, 24 Dec 2014) $ #$Revision: 129039 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/60/7116092.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_7116092 loop_ _publ_author_name 'Gamal A. I. Moustafa' 'Yuki Saku' 'Hiroshi Aoyama' 'Takehiko Yoshimitsu' _publ_section_title ; A new route to platencin via decarboxylative radical cyclization ; _journal_name_full Chem.Commun. _journal_page_first 15706 _journal_paper_doi 10.1039/C4cc07316A _journal_volume 50 _journal_year 2014 _chemical_compound_source 'synthesis as described' _chemical_formula_moiety 'C13 H18 O2' _chemical_formula_sum 'C26 H36 O4' _chemical_formula_weight 412.55 _chemical_melting_point 383.15 _chemical_name_systematic '(3RS,6RS,6aRS,11bRS)-8,11-dimethoxy-6a-methyl-2-oxo-3,4,5,6,6a,7-hexahydro-2H-3,11b-methanoindeno[1,2-b]oxocin-6-yl methanesulfonate (16)' _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 15 _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_creation_date 2014-06-02T15:03:07-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 90.919(14) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.001(11) _cell_length_b 11.207(13) _cell_length_c 20.96(2) _cell_measurement_reflns_used 2531 _cell_measurement_temperature 103(2) _cell_measurement_theta_max 27.47 _cell_measurement_theta_min 3.0498 _cell_measurement_wavelength 0.71073 _cell_volume 2114(4) _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007), SORTAV (Blessing, 1995)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _diffrn_ambient_temperature 103(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 14.7059 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.968 _diffrn_measurement_device 'quarter \C-circle diffractometer' _diffrn_measurement_method 'phi or omega oscillation scans' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_laue_measured_fraction_full 0.988 _diffrn_reflns_laue_measured_fraction_max 0.968 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 15219 _diffrn_reflns_point_group_measured_fraction_max 0.968 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.787 _diffrn_reflns_theta_min 3.073 _diffrn_source 'sealed x-ray tube' _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 896 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: n-hexane' _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.947 _refine_diff_density_min -0.512 _refine_diff_density_rms 0.112 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.594 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 136 _refine_ls_number_reflns 2429 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.594 _refine_ls_R_factor_all 0.1542 _refine_ls_R_factor_gt 0.1327 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3926 _refine_ls_wR_factor_ref 0.4116 _reflns_number_gt 1853 _reflns_number_total 2429 _reflns_threshold_expression 'I > 2\s(I)' _[local]_cod_data_source_file c4cc07316a2.cif _[local]_cod_data_source_block c13h18o2 _[local]_cod_cif_authors_sg_H-M 'C 2/c' _cod_database_code 7116092 _diffrn_reflns_point_group_measured_fraction_ful 0.988 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -x,y,1/2-z 3 1/2+x,1/2+y,z 4 1/2-x,1/2+y,1/2-z 5 -x,-y,-z 6 x,-y,1/2+z 7 1/2-x,1/2-y,-z 8 1/2+x,1/2-y,1/2+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_calc_flag C1 C 0.1188(4) 0.6033(3) 0.86651(18) 0.0315(9) Uani 1 d C2 C 0.0825(4) 0.7294(3) 0.83975(19) 0.0323(9) Uani 1 d H2 H 0.0063 0.719 0.805 0.039 Uiso 1 calc C3 C 0.0121(4) 0.8039(3) 0.89155(19) 0.0339(9) Uani 1 d C4 C 0.3566(4) 0.6966(3) 0.8192(2) 0.0385(10) Uani 1 d H4 H 0.4488 0.7326 0.8015 0.046 Uiso 1 calc C5 C -0.0218(4) 0.5492(3) 0.89314(19) 0.0350(9) Uani 1 d H5A H -0.0936 0.5358 0.8576 0.042 Uiso 1 calc H5B H 0.0026 0.4705 0.912 0.042 Uiso 1 calc C6 C -0.1279(4) 0.7497(3) 0.9178(2) 0.0357(9) Uani 1 d H6 H -0.167 0.8009 0.9528 0.043 Uiso 1 calc C7 C 0.2233(4) 0.7814(3) 0.8089(2) 0.0396(10) Uani 1 d H7A H 0.205 0.793 0.7626 0.048 Uiso 1 calc H7B H 0.2463 0.8601 0.828 0.048 Uiso 1 calc C8 C -0.0944(4) 0.6254(3) 0.9430(2) 0.0399(10) Uani 1 d H8A H -0.0278 0.6314 0.9809 0.048 Uiso 1 calc H8B H -0.188 0.587 0.9564 0.048 Uiso 1 calc C9 C 0.1802(5) 0.5282(3) 0.8126(2) 0.0411(10) Uani 1 d H9A H 0.1977 0.4459 0.8281 0.049 Uiso 1 calc H9B H 0.1058 0.5243 0.7773 0.049 Uiso 1 calc C10 C 0.2419(4) 0.6163(3) 0.91758(19) 0.0367(9) Uani 1 d H10A H 0.2052 0.6644 0.9537 0.044 Uiso 1 calc H10B H 0.2705 0.5367 0.934 0.044 Uiso 1 calc C11 C 0.3747(4) 0.6764(3) 0.8889(2) 0.0382(9) Uani 1 d C12 C 0.3239(5) 0.5785(3) 0.7875(2) 0.0445(11) Uani 1 d H12A H 0.4062 0.522 0.7964 0.053 Uiso 1 calc H12B H 0.3154 0.5895 0.7407 0.053 Uiso 1 calc C13 C 0.0677(5) 0.9028(3) 0.9170(2) 0.0473(11) Uani 1 d H13A H 0.0195 0.9398 0.9518 0.057 Uiso 1 calc H13B H 0.1558 0.9367 0.9004 0.057 Uiso 1 calc O1 O 0.4871(3) 0.6998(2) 0.92049(15) 0.0432(8) Uani 1 d O2 O -0.2353(3) 0.7429(3) 0.86608(15) 0.0451(8) Uani 1 d H2A H -0.1978 0.7071 0.835 0.068 Uiso 1 calc 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 0.0320(18) 0.0257(15) 0.037(2) 0.0005(12) 0.0075(16) -0.0028(11) C2 0.038(2) 0.0285(16) 0.031(2) 0.0055(12) 0.0062(16) 0.0003(12) C3 0.038(2) 0.0311(16) 0.033(2) 0.0021(12) 0.0030(17) -0.0056(13) C4 0.030(2) 0.051(2) 0.035(2) 0.0021(15) 0.0067(17) -0.0001(14) C5 0.0332(19) 0.0320(17) 0.040(2) 0.0022(13) 0.0033(16) -0.0072(13) C6 0.0323(19) 0.0361(18) 0.039(2) 0.0034(14) 0.0083(17) 0.0010(13) C7 0.039(2) 0.0372(18) 0.043(3) 0.0045(14) 0.0089(19) -0.0051(14) C8 0.036(2) 0.0381(19) 0.046(3) 0.0032(14) 0.0048(18) -0.0113(14) C9 0.042(2) 0.0400(19) 0.041(2) -0.0043(14) 0.0061(18) 0.0092(15) C10 0.032(2) 0.0374(18) 0.040(2) 0.0044(14) -0.0026(17) -0.0026(13) C11 0.0288(19) 0.045(2) 0.041(2) 0.0040(15) 0.0059(17) -0.0012(14) C12 0.043(2) 0.049(2) 0.042(3) -0.0037(16) 0.0125(19) 0.0078(16) C13 0.056(3) 0.0373(19) 0.049(3) -0.0072(15) 0.006(2) -0.0092(16) O1 0.0303(16) 0.0576(17) 0.0415(19) 0.0059(12) -0.0035(13) -0.0073(11) O2 0.0381(17) 0.0587(17) 0.0385(19) 0.0031(12) 0.0004(14) 0.0080(12) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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 C5 C1 C9 111.6(3) C5 C1 C10 112.2(3) C9 C1 C10 107.7(3) C5 C1 C2 109.0(3) C9 C1 C2 108.2(3) C10 C1 C2 108.1(3) C3 C2 C7 116.5(3) C3 C2 C1 109.3(3) C7 C2 C1 109.0(3) C3 C2 H2 107.2 C7 C2 H2 107.2 C1 C2 H2 107.2 C13 C3 C6 120.2(4) C13 C3 C2 126.1(4) C6 C3 C2 113.5(3) C11 C4 C12 108.5(3) C11 C4 C7 107.7(3) C12 C4 C7 109.4(4) C11 C4 H4 110.4 C12 C4 H4 110.4 C7 C4 H4 110.4 C8 C5 C1 113.7(3) C8 C5 H5A 108.8 C1 C5 H5A 108.8 C8 C5 H5B 108.8 C1 C5 H5B 108.8 H5A C5 H5B 107.7 O2 C6 C3 107.5(3) O2 C6 C8 109.9(3) C3 C6 C8 109.5(3) O2 C6 H6 110 C3 C6 H6 110 C8 C6 H6 110 C4 C7 C2 110.5(3) C4 C7 H7A 109.6 C2 C7 H7A 109.6 C4 C7 H7B 109.6 C2 C7 H7B 109.6 H7A C7 H7B 108.1 C5 C8 C6 111.3(3) C5 C8 H8A 109.4 C6 C8 H8A 109.4 C5 C8 H8B 109.4 C6 C8 H8B 109.4 H8A C8 H8B 108 C12 C9 C1 112.0(3) C12 C9 H9A 109.2 C1 C9 H9A 109.2 C12 C9 H9B 109.2 C1 C9 H9B 109.2 H9A C9 H9B 107.9 C11 C10 C1 109.5(3) C11 C10 H10A 109.8 C1 C10 H10A 109.8 C11 C10 H10B 109.8 C1 C10 H10B 109.8 H10A C10 H10B 108.2 O1 C11 C4 125.0(4) O1 C11 C10 122.2(4) C4 C11 C10 112.7(3) C4 C12 C9 109.7(3) C4 C12 H12A 109.7 C9 C12 H12A 109.7 C4 C12 H12B 109.7 C9 C12 H12B 109.7 H12A C12 H12B 108.2 C3 C13 H13A 120 C3 C13 H13B 120 H13A C13 H13B 120 C6 O2 H2A 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C5 1.517(5) C1 C9 1.521(5) C1 C10 1.535(5) C1 C2 1.553(5) C2 C3 1.517(5) C2 C7 1.546(5) C2 H2 1 C3 C13 1.324(5) C3 C6 1.511(5) C4 C11 1.485(6) C4 C12 1.508(6) C4 C7 1.543(6) C4 H4 1 C5 C8 1.507(5) C5 H5A 0.99 C5 H5B 0.99 C6 O2 1.443(5) C6 C8 1.519(5) C6 H6 1 C7 H7A 0.99 C7 H7B 0.99 C8 H8A 0.99 C8 H8B 0.99 C9 C12 1.513(6) C9 H9A 0.99 C9 H9B 0.99 C10 C11 1.506(5) C10 H10A 0.99 C10 H10B 0.99 C11 O1 1.228(5) C12 H12A 0.99 C12 H12B 0.99 C13 H13A 0.95 C13 H13B 0.95 O2 H2A 0.84 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 C5 C1 C2 C3 55.1(4) C9 C1 C2 C3 176.5(3) C10 C1 C2 C3 -67.1(4) C5 C1 C2 C7 -176.6(3) C9 C1 C2 C7 -55.1(4) C10 C1 C2 C7 61.2(4) C7 C2 C3 C13 -7.1(6) C1 C2 C3 C13 116.9(4) C7 C2 C3 C6 177.9(3) C1 C2 C3 C6 -58.1(4) C9 C1 C5 C8 -175.2(3) C10 C1 C5 C8 63.8(4) C2 C1 C5 C8 -55.8(4) C13 C3 C6 O2 122.2(4) C2 C3 C6 O2 -62.5(4) C13 C3 C6 C8 -118.4(4) C2 C3 C6 C8 56.9(4) C11 C4 C7 C2 -56.1(4) C12 C4 C7 C2 61.7(4) C3 C2 C7 C4 119.7(4) C1 C2 C7 C4 -4.5(4) C1 C5 C8 C6 55.8(4) O2 C6 C8 C5 64.2(4) C3 C6 C8 C5 -53.7(4) C5 C1 C9 C12 -177.6(3) C10 C1 C9 C12 -54.0(4) C2 C1 C9 C12 62.6(4) C5 C1 C10 C11 -177.0(3) C9 C1 C10 C11 59.9(4) C2 C1 C10 C11 -56.8(4) C12 C4 C11 O1 120.7(4) C7 C4 C11 O1 -120.9(4) C12 C4 C11 C10 -56.0(4) C7 C4 C11 C10 62.4(4) C1 C10 C11 O1 178.2(3) C1 C10 C11 C4 -5.1(4) C11 C4 C12 C9 61.6(4) C7 C4 C12 C9 -55.6(5) C1 C9 C12 C4 -5.7(5)