#------------------------------------------------------------------------------ #$Date: 2014-03-15 13:45:36 +0200 (Sat, 15 Mar 2014) $ #$Revision: 106525 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/10/85/7108517.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_7108517 loop_ _publ_author_name 'Hai-Tao Zhu' 'Xue Dong' 'Li-Jing Wang' 'Mei-Jin Zhong' 'Xue-Yuan Liu' 'Yong-Min Liang' _publ_section_title ; Facile synthesis of 2-iodo-spiro[indene-1,1'-isobenzofuran]-3'-ones via iodine-promoted cascade cyclization ; _journal_name_full Chem.Commun. _journal_page_first 10748 _journal_volume 48 _journal_year 2012 _chemical_formula_moiety 'C12 H9 I O2' _chemical_formula_sum 'C12 H9 I O2' _chemical_formula_weight 312.09 _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yab' _space_group_name_H-M_alt 'P 1 21/a 1' _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2011-11-04 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _cell_angle_alpha 90.00 _cell_angle_beta 97.004(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.714(4) _cell_length_b 18.219(10) _cell_length_c 8.198(5) _cell_measurement_reflns_used 3411 _cell_measurement_temperature 569(2) _cell_measurement_theta_max 25.422 _cell_measurement_theta_min 2.503 _cell_volume 1143.6(11) _computing_data_reduction 'SAINT v7.60A (Bruker, 2009)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)/Bruker' _diffrn_ambient_temperature 569(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'MO K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_unetI/netI 0.0379 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 7990 _diffrn_reflns_theta_full 25.50 _diffrn_reflns_theta_max 25.50 _diffrn_reflns_theta_min 2.24 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 2.777 _exptl_absorpt_correction_T_max 0.7458 _exptl_absorpt_correction_T_min 0.3791 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. R(int) was 0.1233 before and 0.0501 after correction. The Ratio of minimum to maximum transmission is 0.508313220703. The \l/2 correction factor is Not present ; _exptl_crystal_density_diffrn 1.813 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.736 _refine_diff_density_min -1.134 _refine_diff_density_rms 0.110 _refine_ls_extinction_coef 0.072(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 138 _refine_ls_number_reflns 2120 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all 0.0594 _refine_ls_R_factor_gt 0.0410 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0216P)^2^+3.1433P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0850 _refine_ls_wR_factor_ref 0.0972 _reflns_number_gt 1603 _reflns_number_total 2120 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c2cc36127b.txt _[local]_cod_data_source_block test_0m _cod_original_cell_volume 1143.5(11) _cod_database_code 7108517 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z' 3 '-x, -y, -z' 4 '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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags C1 C 0.3621(6) 0.6436(2) 0.3803(6) 0.0396(11) Uani 1 1 d . C2 C 0.4980(6) 0.6103(2) 0.4923(5) 0.0384(11) Uani 1 1 d . C3 C 0.5059(8) 0.6098(3) 0.6642(6) 0.0547(14) Uani 1 1 d . H3 H 0.4179 0.6322 0.7143 0.066 Uiso 1 1 calc R C4 C 0.6427(9) 0.5767(3) 0.7585(7) 0.0668(17) Uani 1 1 d . H4 H 0.6459 0.5769 0.8723 0.080 Uiso 1 1 calc R C5 C 0.7749(8) 0.5432(3) 0.6889(7) 0.0643(16) Uani 1 1 d . H5 H 0.8666 0.5210 0.7551 0.077 Uiso 1 1 calc R C6 C 0.7712(7) 0.5426(3) 0.5219(6) 0.0537(13) Uani 1 1 d . H6 H 0.8601 0.5197 0.4737 0.064 Uiso 1 1 calc R C7 C 0.6348(6) 0.5760(2) 0.4251(5) 0.0382(10) Uani 1 1 d . C8 C 0.6374(7) 0.5741(3) 0.2470(6) 0.0460(12) Uani 1 1 d . C9 C 0.3671(6) 0.6425(2) 0.2187(6) 0.0391(10) Uani 1 1 d . C10 C 0.2427(7) 0.6735(3) 0.0837(6) 0.0488(12) Uani 1 1 d . C11 C 0.2468(9) 0.7447(4) 0.0546(9) 0.081(2) Uani 1 1 d . H11A H 0.1713 0.7650 -0.0305 0.098 Uiso 1 1 calc R H11B H 0.3254 0.7746 0.1192 0.098 Uiso 1 1 calc R C12 C 0.1239(8) 0.6205(4) -0.0105(7) 0.0706(17) Uani 1 1 d . H12A H 0.1909 0.5808 -0.0477 0.106 Uiso 1 1 calc R H12B H 0.0611 0.6448 -0.1035 0.106 Uiso 1 1 calc R H12C H 0.0426 0.6016 0.0588 0.106 Uiso 1 1 calc R I1 I 0.15074(6) 0.69411(3) 0.47077(6) 0.0887(3) Uani 1 1 d . O1 O 0.5006(4) 0.60724(18) 0.1520(4) 0.0460(8) Uani 1 1 d . O2 O 0.7488(5) 0.5471(2) 0.1756(5) 0.0714(12) 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 0.041(3) 0.037(2) 0.042(3) 0.001(2) 0.008(2) 0.0043(19) C2 0.052(3) 0.034(2) 0.029(2) -0.0027(19) 0.004(2) -0.008(2) C3 0.075(4) 0.056(3) 0.034(3) -0.005(2) 0.008(3) -0.008(3) C4 0.096(5) 0.069(4) 0.031(3) 0.005(3) -0.012(3) -0.020(3) C5 0.068(4) 0.061(4) 0.056(4) 0.013(3) -0.025(3) -0.012(3) C6 0.046(3) 0.056(3) 0.055(3) 0.009(3) -0.008(2) 0.004(2) C7 0.042(3) 0.033(2) 0.038(3) 0.0045(19) -0.002(2) -0.0034(18) C8 0.046(3) 0.052(3) 0.040(3) 0.002(2) 0.007(2) 0.007(2) C9 0.039(3) 0.038(2) 0.040(3) 0.004(2) 0.004(2) 0.0020(19) C10 0.046(3) 0.054(3) 0.045(3) 0.011(2) -0.002(2) 0.008(2) C11 0.069(4) 0.070(4) 0.097(5) 0.029(4) -0.024(4) 0.001(3) C12 0.068(4) 0.079(4) 0.059(4) 0.001(3) -0.018(3) 0.000(3) I1 0.0870(4) 0.1025(4) 0.0830(4) 0.0047(3) 0.0365(3) 0.0459(3) O1 0.048(2) 0.060(2) 0.0299(17) 0.0030(15) 0.0033(14) 0.0145(16) O2 0.065(3) 0.100(3) 0.052(2) 0.005(2) 0.0191(19) 0.034(2) 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' I I -0.4742 1.8119 '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 C2 C1 I1 119.9(3) C9 C1 C2 121.4(4) C9 C1 I1 118.7(3) C3 C2 C1 125.5(5) C7 C2 C1 117.6(4) C7 C2 C3 116.9(4) C2 C3 H3 119.8 C4 C3 C2 120.4(5) C4 C3 H3 119.8 C3 C4 H4 119.3 C5 C4 C3 121.5(5) C5 C4 H4 119.3 C4 C5 H5 120.2 C6 C5 C4 119.7(5) C6 C5 H5 120.2 C5 C6 H6 120.2 C5 C6 C7 119.6(5) C7 C6 H6 120.2 C2 C7 C8 120.5(4) C6 C7 C2 122.0(4) C6 C7 C8 117.4(4) O1 C8 C7 116.9(4) O2 C8 C7 126.5(5) O2 C8 O1 116.7(4) C1 C9 C10 129.9(4) C1 C9 O1 121.0(4) O1 C9 C10 109.1(4) C11 C10 C9 118.7(5) C11 C10 C12 125.0(5) C12 C10 C9 116.3(4) C10 C11 H11A 120.0 C10 C11 H11B 120.0 H11A C11 H11B 120.0 C10 C12 H12A 109.5 C10 C12 H12B 109.5 C10 C12 H12C 109.5 H12A C12 H12B 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C8 O1 C9 122.6(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.441(6) C1 C9 1.330(6) C1 I1 2.086(4) C2 C3 1.403(6) C2 C7 1.396(6) C3 H3 0.9300 C3 C4 1.370(8) C4 H4 0.9300 C4 C5 1.371(9) C5 H5 0.9300 C5 C6 1.366(8) C6 H6 0.9300 C6 C7 1.380(7) C7 C8 1.463(6) C8 O1 1.373(6) C8 O2 1.202(6) C9 C10 1.485(7) C9 O1 1.382(5) C10 C11 1.320(8) C10 C12 1.482(8) C11 H11A 0.9300 C11 H11B 0.9300 C12 H12A 0.9600 C12 H12B 0.9600 C12 H12C 0.9600 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 C1 C2 C3 C4 -179.6(5) C1 C2 C7 C6 179.9(4) C1 C2 C7 C8 -0.5(6) C1 C9 C10 C11 78.0(7) C1 C9 C10 C12 -103.0(6) C1 C9 O1 C8 -2.4(7) C2 C1 C9 C10 -179.6(5) C2 C1 C9 O1 1.9(7) C2 C3 C4 C5 0.0(8) C2 C7 C8 O1 0.1(7) C2 C7 C8 O2 179.0(5) C3 C2 C7 C6 0.6(7) C3 C2 C7 C8 -179.8(4) C3 C4 C5 C6 0.0(9) C4 C5 C6 C7 0.3(8) C5 C6 C7 C2 -0.6(7) C5 C6 C7 C8 179.8(5) C6 C7 C8 O1 179.7(4) C6 C7 C8 O2 -1.4(8) C7 C2 C3 C4 -0.3(7) C7 C8 O1 C9 1.3(6) C9 C1 C2 C3 178.8(5) C9 C1 C2 C7 -0.5(6) C10 C9 O1 C8 178.9(4) I1 C1 C2 C3 -1.9(6) I1 C1 C2 C7 178.8(3) I1 C1 C9 C10 1.0(7) I1 C1 C9 O1 -177.4(3) O1 C9 C10 C11 -103.4(6) O1 C9 C10 C12 75.7(6) O2 C8 O1 C9 -177.7(5) _journal_paper_doi 10.1039/c2cc36127b