#------------------------------------------------------------------------------ #$Date: 2013-12-28 07:07:06 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91932 $ #$URL: svn://www.crystallography.net/cod/cif/1/50/78/1507840.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_1507840 loop_ _publ_author_name 'Zhu, Chenjie' 'Yoshimura, Akira' 'Ji, Lei' 'Wei, Yunyang' 'Nemykin, Victor N.' 'Zhdankin, Viktor V.' _publ_section_title ; Design, Preparation, X-ray Crystal Structure, and Reactivity ofo-Alkoxyphenyliodonium Bis(methoxycarbonyl)methanide, a Highly Soluble Carbene Precursor ; _journal_issue 12 _journal_name_full 'Organic Letters' _journal_page_first 3170 _journal_volume 14 _journal_year 2012 _chemical_formula_moiety 'C12 H13 I1 O5' _chemical_formula_sum 'C12 H13 I O5' _chemical_formula_weight 364.14 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _cell_angle_alpha 90 _cell_angle_beta 90.848(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.5395(5) _cell_length_b 7.7736(5) _cell_length_c 19.6400(13) _cell_measurement_reflns_used 2971 _cell_measurement_temperature 123 _cell_measurement_theta_max 25 _cell_measurement_theta_min 2 _cell_volume 1303.61(14) _computing_cell_refinement 'CrystalClear 2.0' _computing_data_collection 'CrystalClear 2.0' _computing_data_reduction 'CrystalStructure 4.0' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _diffrn_ambient_temperature 123 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device 'Rigaku Rapid II' _diffrn_measurement_device_type 'Image Plate' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.048 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 11928 _diffrn_reflns_theta_full 27.483 _diffrn_reflns_theta_max 27.483 _diffrn_reflns_theta_min 3.343 _diffrn_standards_decay_% 0.00 _diffrn_standards_interval_time 2 _diffrn_standards_number 2971 _exptl_absorpt_coefficient_mu 2.467 _exptl_absorpt_correction_T_max 0.50 _exptl_absorpt_correction_T_min 0.26 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.855 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 712 _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_min 0.100 _refine_diff_density_max 4.40 _refine_diff_density_min -1.63 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 1.0164 _refine_ls_hydrogen_treatment none _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 2953 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0448 _refine_ls_shift/su_max 0.0005379 _refine_ls_shift/su_mean 0.0000161 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.07P)^2^ + 5.77P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1206 _refine_ls_wR_factor_gt 0.1177 _refine_ls_wR_factor_ref 0.1206 _reflns_limit_h_max 11 _reflns_limit_h_min -11 _reflns_limit_k_max 10 _reflns_limit_k_min 0 _reflns_limit_l_max 25 _reflns_limit_l_min 0 _reflns_number_gt 2669 _reflns_number_total 2971 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _oxford_refine_ls_r_factor_ref 0.0485 _oxford_refine_ls_scale 0.694(2) _oxford_reflns_number_all 2953 _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _[local]_cod_data_source_file ol301268j_si_002.cif _[local]_cod_data_source_block 1 _[local]_cod_cif_authors_sg_H-M 'P 1 21/n 1 ' _[local]_cod_chemical_formula_sum_orig 'C12 H13 I1 O5' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 1891 2012-01-12 08:04:46Z andrius ; _cod_database_code 1507840 _iucr_refine_instruction_details_constraints ; BLOCK SCALE X'S, U'S RIDE C ( 10,X'S) H ( 9,X'S) H ( 10,X'S) H ( 8,X'S) RIDE C ( 12,X'S) H ( 13,X'S) H ( 12,X'S) H ( 11,X'S) RIDE C ( 7,X'S) H ( 7,X'S) H ( 5,X'S) H ( 6,X'S) RIDE C ( 3,X'S) H ( 1,X'S) RIDE C ( 4,X'S) H ( 2,X'S) RIDE C ( 5,X'S) H ( 3,X'S) RIDE C ( 6,X'S) H ( 4,X'S) END ; _iucr_refine_instruction_details_restraints ; NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn I1 I 0.94725(3) 0.67366(4) 0.344948(14) 0.0232 1.0000 Uani . C8 C 0.7878(5) 0.5648(6) 0.2798(2) 0.0237 1.0000 Uani . C9 C 0.6352(5) 0.5443(6) 0.3091(2) 0.0251 1.0000 Uani . O3 O 0.5251(4) 0.4915(5) 0.26294(18) 0.0327 1.0000 Uani . C10 C 0.3702(6) 0.4710(9) 0.2899(3) 0.0413 1.0000 Uani . O2 O 0.6032(4) 0.5705(5) 0.36845(18) 0.0311 1.0000 Uani . C11 C 0.8354(5) 0.5260(6) 0.2118(2) 0.0235 1.0000 Uani . O4 O 0.7488(4) 0.4827(5) 0.16481(17) 0.0283 1.0000 Uani . O5 O 0.9924(4) 0.5387(5) 0.20372(18) 0.0321 1.0000 Uani . C12 C 1.0465(7) 0.4966(10) 0.1365(3) 0.0428 1.0000 Uani . C1 C 1.0406(5) 0.4525(6) 0.3936(2) 0.0218 1.0000 Uani . C2 C 1.1546(5) 0.4886(6) 0.4431(2) 0.0240 1.0000 Uani . O1 O 1.1946(4) 0.6571(4) 0.44961(19) 0.0271 1.0000 Uani . C7 C 1.3230(6) 0.6969(7) 0.4946(3) 0.0301 1.0000 Uani . C3 C 1.2133(6) 0.3525(7) 0.4817(3) 0.0262 1.0000 Uani . C4 C 1.1577(6) 0.1875(7) 0.4697(3) 0.0308 1.0000 Uani . C5 C 1.0470(7) 0.1533(7) 0.4188(3) 0.0333 1.0000 Uani . C6 C 0.9864(6) 0.2904(7) 0.3803(3) 0.0282 1.0000 Uani . H9 H 0.3013 0.4254 0.2550 0.0662 1.0000 Uiso R H10 H 0.3309 0.5805 0.3046 0.0666 1.0000 Uiso R H8 H 0.3728 0.3936 0.3284 0.0658 1.0000 Uiso R H13 H 1.1583 0.5043 0.1367 0.0680 1.0000 Uiso R H12 H 1.0040 0.5786 0.1047 0.0683 1.0000 Uiso R H11 H 1.0138 0.3820 0.1248 0.0678 1.0000 Uiso R H7 H 1.3383 0.8182 0.4950 0.0471 1.0000 Uiso R H5 H 1.3022 0.6601 0.5400 0.0470 1.0000 Uiso R H6 H 1.4180 0.6429 0.4791 0.0473 1.0000 Uiso R H1 H 1.2886 0.3738 0.5147 0.0318 1.0000 Uiso R H2 H 1.1969 0.0972 0.4972 0.0373 1.0000 Uiso R H3 H 1.0149 0.0421 0.4105 0.0407 1.0000 Uiso R H4 H 0.9073 0.2729 0.3466 0.0342 1.0000 Uiso 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.02058(19) 0.0256(2) 0.02322(19) -0.00010(11) -0.00407(12) -0.00102(10) C8 0.015(2) 0.028(2) 0.027(2) -0.0036(19) -0.0044(17) -0.0025(16) C9 0.023(2) 0.025(2) 0.027(2) 0.0015(19) -0.0013(18) 0.0016(18) O3 0.0182(16) 0.052(2) 0.0283(18) -0.0094(17) -0.0025(13) -0.0008(15) C10 0.018(2) 0.060(4) 0.046(3) -0.013(3) 0.000(2) -0.004(2) O2 0.0245(17) 0.044(2) 0.0246(17) -0.0027(15) 0.0009(14) -0.0019(15) C11 0.022(2) 0.024(2) 0.025(2) 0.0020(18) 0.0003(17) 0.0005(17) O4 0.0277(17) 0.0339(18) 0.0233(16) -0.0002(14) -0.0028(13) -0.0017(14) O5 0.0204(16) 0.049(2) 0.0271(18) -0.0046(16) 0.0030(14) -0.0040(15) C12 0.033(3) 0.068(4) 0.029(3) -0.007(3) 0.011(2) 0.000(3) C1 0.019(2) 0.027(2) 0.019(2) -0.0001(17) 0.0008(16) 0.0032(17) C2 0.020(2) 0.028(2) 0.024(2) -0.0011(19) 0.0047(17) 0.0016(17) O1 0.0238(17) 0.0273(17) 0.0299(18) -0.0001(14) -0.0064(14) 0.0009(13) C7 0.025(2) 0.034(3) 0.032(3) 0.000(2) -0.006(2) -0.0037(19) C3 0.022(2) 0.032(2) 0.024(2) 0.0017(19) 0.0012(18) 0.0060(18) C4 0.030(3) 0.029(2) 0.034(3) 0.004(2) 0.003(2) 0.006(2) C5 0.033(3) 0.026(2) 0.042(3) -0.003(2) 0.004(2) -0.0003(19) C6 0.022(2) 0.035(3) 0.028(2) -0.008(2) -0.0013(19) -0.0024(19) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776 4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 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_publ_flag C8 I1 C1 100.93(18) yes I1 C8 C9 113.3(3) yes I1 C8 C11 118.4(3) yes C9 C8 C11 128.2(4) yes C8 C9 O3 112.8(4) yes C8 C9 O2 125.5(4) yes O3 C9 O2 121.7(4) yes C9 O3 C10 114.7(4) yes O3 C10 H9 109.4 no O3 C10 H10 109.8 no H9 C10 H10 109.1 no O3 C10 H8 110.2 no H9 C10 H8 109.6 no H10 C10 H8 108.6 no C8 C11 O4 125.8(4) yes C8 C11 O5 112.8(4) yes O4 C11 O5 121.4(4) yes C11 O5 C12 114.9(4) yes O5 C12 H13 108.4 no O5 C12 H12 108.8 no H13 C12 H12 109.2 no O5 C12 H11 109.5 no H13 C12 H11 110.1 no H12 C12 H11 110.8 no I1 C1 C2 113.9(3) yes I1 C1 C6 122.6(4) yes C2 C1 C6 123.4(4) yes C1 C2 O1 115.6(4) yes C1 C2 C3 118.0(5) yes O1 C2 C3 126.4(4) yes C2 O1 C7 117.1(4) yes O1 C7 H7 108.8 no O1 C7 H5 111.1 no H7 C7 H5 108.4 no O1 C7 H6 110.5 no H7 C7 H6 108.5 no H5 C7 H6 109.4 no C2 C3 C4 119.4(5) yes C2 C3 H1 119.3 no C4 C3 H1 121.3 no C3 C4 C5 121.8(5) yes C3 C4 H2 118.1 no C5 C4 H2 120.1 no C4 C5 C6 119.0(5) yes C4 C5 H3 120.4 no C6 C5 H3 120.7 no C5 C6 C1 118.5(5) yes C5 C6 H4 121.4 no C1 C6 H4 120.1 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag I1 C8 2.038(4) yes I1 C1 2.117(5) yes C8 C9 1.441(6) yes C8 C11 1.435(7) yes C9 O3 1.360(6) yes C9 O2 1.218(6) yes O3 C10 1.441(6) yes C10 H9 0.964 no C10 H10 0.962 no C10 H8 0.966 no C11 O4 1.221(6) yes C11 O5 1.356(6) yes O5 C12 1.442(6) yes C12 H13 0.957 no C12 H12 0.960 no C12 H11 0.961 no C1 C2 1.394(6) yes C1 C6 1.366(7) yes C2 O1 1.359(6) yes C2 C3 1.392(7) yes O1 C7 1.432(6) yes C7 H7 0.953 no C7 H5 0.955 no C7 H6 0.966 no C3 C4 1.387(7) yes C3 H1 0.921 no C4 C5 1.390(8) yes C4 H2 0.945 no C5 C6 1.401(8) yes C5 H3 0.921 no C6 H4 0.949 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C3 H1 O2 2_766 157.25(14) 0.92115 2.499 3.367(7) yes _journal_paper_doi 10.1021/ol301268j