data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Kita, Yasuyuki' _publ_contact_author_email kita@ph.ritsumei.ac.jp _publ_section_title ; Designer m-oxo-bridged hypervalent iodine(III) organocatalysts for greener oxidations ; loop_ _publ_author_name T.Dohi N.Takenaga K.Fukushima T.Uchiyama D.Kato M.Shiro ; H.Fujioka ; Y.Kita data__RGK1792cfmlt _database_code_depnum_ccdc_archive 'CCDC 779814' #TrackingRef 'CIF.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C20 H22 I2 O5 ' _chemical_formula_moiety 'C20 H22 I2 O5 ' _chemical_formula_weight 596.20 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 9.9139(7) _cell_length_b 10.7578(8) _cell_length_c 20.8239(15) _cell_angle_alpha 90.0000 _cell_angle_beta 104.424(7) _cell_angle_gamma 90.0000 _cell_volume 2150.9(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2777 _cell_measurement_theta_min 4.1 _cell_measurement_theta_max 66.9 _cell_measurement_temperature 153.1 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.841 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152.00 _exptl_absorpt_coefficient_mu 23.192 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.270 _exptl_absorpt_correction_T_max 0.395 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 24378 _diffrn_reflns_av_R_equivalents 0.098 _diffrn_reflns_theta_max 68.10 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 68.10 _diffrn_measured_fraction_theta_full 0.996 _diffrn_ambient_temperature 153.1 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3905 _reflns_number_gt 3686 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1159 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 3905 _refine_ls_number_parameters 250 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0437P)^2^+6.5609P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0040 _refine_diff_density_max 2.34 _refine_diff_density_min -1.32 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; I I -0.326 6.836 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.049 0.032 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 I1 I 0.64081(4) 0.79269(4) 0.487116(17) 0.03307(14) Uani 1.00 1 d . . . I2 I 0.57550(4) 0.47612(3) 0.418505(18) 0.03029(14) Uani 1.00 1 d . . . O1 O 0.5793(4) 0.6101(3) 0.48965(19) 0.0361(10) Uani 1.00 1 d . . . O2 O 0.6875(5) 0.9850(4) 0.4611(2) 0.0470(11) Uani 1.00 1 d . . . O3 O 0.8531(6) 0.9811(5) 0.5551(2) 0.0600(14) Uani 1.00 1 d . . . O4 O 0.6064(4) 0.3368(4) 0.3444(2) 0.0380(10) Uani 1.00 1 d . . . O5 O 0.4186(4) 0.2555(4) 0.3696(2) 0.0448(11) Uani 1.00 1 d . . . C1 C 0.5277(6) 0.7984(5) 0.3872(2) 0.0261(12) Uani 1.00 1 d . . . C2 C 0.4010(6) 0.8624(5) 0.3716(2) 0.0333(13) Uani 1.00 1 d . . . C3 C 0.3248(6) 0.8672(5) 0.3064(3) 0.0346(13) Uani 1.00 1 d . . . C4 C 0.3784(6) 0.8064(5) 0.2584(3) 0.0318(13) Uani 1.00 1 d . . . C5 C 0.5059(6) 0.7448(5) 0.2736(2) 0.0272(12) Uani 1.00 1 d . . . C6 C 0.5850(5) 0.7413(5) 0.3405(2) 0.0259(11) Uani 1.00 1 d . . . C7 C 0.7252(6) 0.6808(5) 0.3600(2) 0.0259(12) Uani 1.00 1 d . . . C8 C 0.8430(6) 0.7406(5) 0.3489(2) 0.0286(12) Uani 1.00 1 d . . . C9 C 0.9708(6) 0.6795(6) 0.3664(3) 0.0341(13) Uani 1.00 1 d . . . C10 C 0.9875(6) 0.5591(6) 0.3930(2) 0.0352(14) Uani 1.00 1 d . . . C11 C 0.8712(6) 0.5005(6) 0.4060(3) 0.0343(14) Uani 1.00 1 d . . . C12 C 0.7433(5) 0.5625(5) 0.3900(2) 0.0258(11) Uani 1.00 1 d . . . C13 C 0.1920(6) 0.9415(6) 0.2873(3) 0.0434(16) Uani 1.00 1 d . . . C14 C 0.5619(7) 0.6875(5) 0.2190(3) 0.0366(14) Uani 1.00 1 d . . . C15 C 0.8355(7) 0.8716(5) 0.3221(3) 0.0398(15) Uani 1.00 1 d . . . C16 C 1.1284(7) 0.4958(7) 0.4090(3) 0.0499(18) Uani 1.00 1 d . . . C17 C 0.7977(8) 1.0320(6) 0.5025(3) 0.0449(17) Uani 1.00 1 d . . . C18 C 0.8486(10) 1.1543(7) 0.4820(4) 0.067(2) Uani 1.00 1 d . . . C19 C 0.5144(6) 0.2477(6) 0.3416(2) 0.0366(14) Uani 1.00 1 d . . . C20 C 0.5334(8) 0.1345(6) 0.3022(3) 0.0525(19) Uani 1.00 1 d . . . H2 H 0.3678 0.9021 0.4054 0.040 Uiso 1.00 1 c R . . H4 H 0.3252 0.8073 0.2136 0.038 Uiso 1.00 1 c R . . H9 H 1.0507 0.7215 0.3600 0.041 Uiso 1.00 1 c R . . H11 H 0.8790 0.4200 0.4253 0.041 Uiso 1.00 1 c R . . H13A H 0.1127 0.8851 0.2726 0.052 Uiso 1.00 1 c R . . H13B H 0.1963 0.9988 0.2513 0.052 Uiso 1.00 1 c R . . H13C H 0.1806 0.9891 0.3258 0.052 Uiso 1.00 1 c R . . H14A H 0.6288 0.7446 0.2071 0.044 Uiso 1.00 1 c R . . H14B H 0.4848 0.6722 0.1801 0.044 Uiso 1.00 1 c R . . H14C H 0.6083 0.6088 0.2346 0.044 Uiso 1.00 1 c R . . H15A H 0.8337 0.8692 0.2749 0.048 Uiso 1.00 1 c R . . H15B H 0.9172 0.9185 0.3462 0.048 Uiso 1.00 1 c R . . H15C H 0.7507 0.9119 0.3279 0.048 Uiso 1.00 1 c R . . H16A H 1.1685 0.5013 0.3705 0.060 Uiso 1.00 1 c R . . H16B H 1.1174 0.4083 0.4197 0.060 Uiso 1.00 1 c R . . H16C H 1.1904 0.5370 0.4471 0.060 Uiso 1.00 1 c R . . H18A H 0.8836 1.1419 0.4424 0.080 Uiso 1.00 1 c R . . H18B H 0.9237 1.1864 0.5181 0.080 Uiso 1.00 1 c R . . H18C H 0.7715 1.2140 0.4721 0.080 Uiso 1.00 1 c R . . H20A H 0.6091 0.1493 0.2805 0.063 Uiso 1.00 1 c R . . H20B H 0.4470 0.1178 0.2684 0.063 Uiso 1.00 1 c R . . H20C H 0.5564 0.0628 0.3319 0.063 Uiso 1.00 1 c R . . 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 I1 0.0479(2) 0.0320(2) 0.0223(2) 0.00222(16) 0.01449(19) 0.00061(15) I2 0.0388(2) 0.0300(2) 0.0266(2) -0.00037(15) 0.01675(18) 0.00443(15) O1 0.060(2) 0.025(2) 0.032(2) -0.0038(19) 0.027(2) -0.0033(18) O2 0.059(3) 0.039(2) 0.041(2) -0.009(2) 0.008(2) 0.002(2) O3 0.076(3) 0.064(3) 0.036(3) -0.009(2) 0.006(2) 0.001(2) O4 0.048(2) 0.039(2) 0.032(2) -0.005(2) 0.019(2) -0.000(2) O5 0.051(2) 0.053(2) 0.035(2) -0.008(2) 0.020(2) -0.000(2) C1 0.032(3) 0.030(3) 0.017(2) -0.002(2) 0.009(2) 0.003(2) C2 0.041(3) 0.037(3) 0.028(3) 0.004(2) 0.020(2) 0.002(2) C3 0.030(3) 0.035(3) 0.041(3) -0.001(2) 0.015(2) 0.003(2) C4 0.035(3) 0.034(3) 0.026(3) -0.005(2) 0.006(2) 0.003(2) C5 0.038(3) 0.023(2) 0.025(2) -0.008(2) 0.015(2) -0.001(2) C6 0.032(2) 0.024(2) 0.024(2) -0.005(2) 0.011(2) 0.005(2) C7 0.035(3) 0.028(2) 0.018(2) 0.000(2) 0.012(2) -0.004(2) C8 0.034(3) 0.031(3) 0.023(2) -0.001(2) 0.011(2) -0.002(2) C9 0.036(3) 0.040(3) 0.031(3) -0.002(2) 0.016(2) -0.007(2) C10 0.037(3) 0.046(3) 0.024(3) 0.011(2) 0.011(2) 0.001(2) C11 0.043(3) 0.035(3) 0.025(3) 0.010(2) 0.009(2) 0.005(2) C12 0.034(3) 0.027(2) 0.019(2) 0.000(2) 0.011(2) -0.001(2) C13 0.035(3) 0.047(4) 0.049(4) 0.009(3) 0.012(3) 0.007(3) C14 0.048(3) 0.037(3) 0.026(3) 0.005(2) 0.013(2) -0.005(2) C15 0.046(3) 0.038(3) 0.042(3) -0.006(3) 0.021(3) 0.009(3) C16 0.037(3) 0.068(5) 0.044(4) 0.014(3) 0.011(3) -0.002(3) C17 0.068(4) 0.039(4) 0.032(3) -0.002(3) 0.021(3) -0.008(3) C18 0.098(6) 0.046(4) 0.054(5) -0.014(4) 0.015(4) -0.004(4) C19 0.050(3) 0.041(3) 0.021(3) -0.005(3) 0.012(2) 0.005(2) C20 0.075(5) 0.047(4) 0.041(4) -0.016(3) 0.025(3) -0.002(3) #============================================================================== _computing_data_collection 'PROCESS-AUTO (Rigaku, 1998)' _computing_cell_refinement 'PROCESS-AUTO (Rigaku, 1998)' _computing_data_reduction 'CrystalStructure (Rigaku & RAC 2007)' _computing_structure_solution 'SIR2004 (Burla, 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_publication_material 'CrystalStructure (Rigaku & RAC 2007)' _computing_molecular_graphics 'ORTEP (Johnson, 1976)' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 I1 O1 2.062(4) yes . . I1 O2 2.216(4) yes . . I1 C1 2.104(5) yes . . I2 O1 2.060(4) yes . . I2 O4 2.226(4) yes . . I2 C12 2.115(6) yes . . O2 C17 1.313(8) yes . . O3 C17 1.224(8) yes . . O4 C19 1.314(8) yes . . O5 C19 1.236(8) yes . . C1 C2 1.398(8) yes . . C1 C6 1.385(8) yes . . C2 C3 1.381(8) yes . . C3 C4 1.405(9) yes . . C3 C13 1.507(8) yes . . C4 C5 1.392(8) yes . . C5 C6 1.419(7) yes . . C5 C14 1.514(9) yes . . C6 C7 1.496(7) yes . . C7 C8 1.402(8) yes . . C7 C12 1.410(7) yes . . C8 C9 1.393(8) yes . . C8 C15 1.510(8) yes . . C9 C10 1.402(9) yes . . C10 C11 1.398(9) yes . . C10 C16 1.514(9) yes . . C11 C12 1.397(8) yes . . C17 C18 1.509(11) yes . . C19 C20 1.506(10) yes . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 O1 I1 O2 167.66(15) yes . . . O1 I1 C1 87.99(18) yes . . . O2 I1 C1 79.85(19) yes . . . O1 I2 O4 171.18(17) yes . . . O1 I2 C12 91.1(2) yes . . . O4 I2 C12 81.25(19) yes . . . I1 O1 I2 126.9(2) yes . . . I1 O2 C17 112.9(4) yes . . . I2 O4 C19 108.0(4) yes . . . I1 C1 C2 118.1(4) yes . . . I1 C1 C6 118.1(3) yes . . . C2 C1 C6 123.9(4) yes . . . C1 C2 C3 119.1(5) yes . . . C2 C3 C4 118.1(5) yes . . . C2 C3 C13 120.5(6) yes . . . C4 C3 C13 121.4(5) yes . . . C3 C4 C5 122.9(5) yes . . . C4 C5 C6 118.9(5) yes . . . C4 C5 C14 120.3(4) yes . . . C6 C5 C14 120.7(5) yes . . . C1 C6 C5 117.0(5) yes . . . C1 C6 C7 121.2(4) yes . . . C5 C6 C7 121.7(5) yes . . . C6 C7 C8 120.8(5) yes . . . C6 C7 C12 121.3(5) yes . . . C8 C7 C12 117.9(5) yes . . . C7 C8 C9 118.8(5) yes . . . C7 C8 C15 121.5(5) yes . . . C9 C8 C15 119.7(5) yes . . . C8 C9 C10 123.3(6) yes . . . C9 C10 C11 118.1(5) yes . . . C9 C10 C16 120.9(6) yes . . . C11 C10 C16 121.0(6) yes . . . C10 C11 C12 118.8(5) yes . . . I2 C12 C7 119.9(4) yes . . . I2 C12 C11 117.0(4) yes . . . C7 C12 C11 123.0(5) yes . . . O2 C17 O3 121.9(6) yes . . . O2 C17 C18 115.6(5) yes . . . O3 C17 C18 122.4(6) yes . . . O4 C19 O5 122.4(6) yes . . . O4 C19 C20 115.8(6) yes . . . O5 C19 C20 121.9(6) yes . . . C1 C2 H2 120.4 no . . . C3 C2 H2 120.4 no . . . C3 C4 H4 118.5 no . . . C5 C4 H4 118.6 no . . . C8 C9 H9 118.3 no . . . C10 C9 H9 118.3 no . . . #===END========================================================================