#------------------------------------------------------------------------------ #$Date: 2015-02-25 15:01:53 +0200 (Wed, 25 Feb 2015) $ #$Revision: 132410 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/07/51/4075165.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_4075165 loop_ _publ_author_name 'Herrmann, Wolfgang A.' 'Sch\"utz, Jan' 'Frey, Guido D.' 'Herdtweck, Eberhardt' _publ_section_title ; N-Heterocyclic Carbenes:  Synthesis, Structures, and Electronic Ligand Properties†,‡ ; _journal_issue 10 _journal_name_full Organometallics _journal_page_first 2437 _journal_paper_doi 10.1021/om0600801 _journal_volume 25 _journal_year 2006 _chemical_formula_moiety 'C12 H19 I Ir N3' _chemical_formula_sum 'C12 H19 I Ir N3' _chemical_formula_weight 524.42 _chemical_name_systematic ? _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _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 _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 93.2966(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.3634(2) _cell_length_b 16.0249(4) _cell_length_c 11.7962(3) _cell_measurement_reflns_used 2629 _cell_measurement_temperature 123(1) _cell_measurement_theta_max 25.32 _cell_measurement_theta_min 2.15 _cell_volume 1389.62(6) _computing_cell_refinement 'DENZO (Nonius, 2001b)' _computing_data_collection 'Kappa-CCD Control Software (Nonius, 2001a)' _computing_data_reduction 'DENZO (Nonius, 2001b)' _computing_molecular_graphics 'PLATON (Spek, 2001)' _computing_publication_material 'PLATON (Spek, 2001)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _diffrn_ambient_temperature 123(1) _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 18 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Nonius \k-CCD diffractometer' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'NONIUS FR 591 rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0671 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 28259 _diffrn_reflns_theta_full 25.32 _diffrn_reflns_theta_max 25.32 _diffrn_reflns_theta_min 2.15 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 11.813 _exptl_absorpt_correction_T_max 0.557 _exptl_absorpt_correction_T_min 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(applied during the scaling procedure; Nonius, 2001b)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 2.507 _exptl_crystal_density_meas ? _exptl_crystal_density_method none _exptl_crystal_description plate _exptl_crystal_F_000 968 _exptl_crystal_size_max 0.81 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _refine_diff_density_max 1.133 _refine_diff_density_min -0.906 _refine_diff_density_rms 0.165 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 157 _refine_ls_number_reflns 2521 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.056 _refine_ls_R_factor_all 0.0253 _refine_ls_R_factor_gt 0.0231 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(Fo^2^)+(0.0387P)^2^+2.5784P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.0633 _reflns_number_gt 2353 _reflns_number_total 2521 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file om0600801si20060125_123006.cif _[local]_cod_data_source_block JSCF-4356-123 _[local]_cod_cif_authors_sg_H-M 'P 21/n' _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 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'none' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_database_code 4075165 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z 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 Ir 0.0196(1) 0.0190(1) 0.0160(1) 0.0001(1) 0.0010(1) -0.0012(1) I 0.0389(2) 0.0246(2) 0.0252(2) -0.0015(1) 0.0093(1) 0.0057(1) N1 0.036(2) 0.019(2) 0.021(2) 0.0041(17) 0.0047(17) 0.0055(18) N2 0.033(2) 0.022(2) 0.024(2) 0.0003(18) 0.0033(17) -0.0063(19) N3 0.060(4) 0.023(3) 0.029(3) 0.001(2) 0.017(2) -0.004(2) C1 0.028(2) 0.035(3) 0.011(2) 0.004(2) 0.0054(18) 0.004(2) C2 0.062(4) 0.020(3) 0.030(3) 0.002(2) 0.016(3) 0.001(2) C3 0.034(3) 0.042(4) 0.039(3) 0.002(3) -0.008(3) -0.015(2) C4 0.034(3) 0.031(3) 0.030(3) 0.002(2) -0.007(2) 0.007(2) C5 0.027(2) 0.017(2) 0.026(2) -0.002(2) 0.0088(19) 0.000(2) C6 0.037(3) 0.012(2) 0.024(2) 0.0053(19) 0.005(2) -0.002(2) C7 0.048(3) 0.027(3) 0.022(3) -0.004(2) 0.001(2) -0.015(2) C8 0.034(3) 0.034(3) 0.032(3) -0.001(2) 0.001(2) -0.011(2) C9 0.024(2) 0.024(3) 0.023(2) 0.0002(19) 0.0075(19) -0.0110(19) C10 0.030(2) 0.022(3) 0.018(2) 0.0024(19) 0.0059(18) -0.002(2) C11 0.036(3) 0.026(3) 0.028(3) 0.009(2) 0.003(2) 0.006(2) C12 0.034(3) 0.037(3) 0.032(3) 0.005(2) 0.008(2) 0.006(2) N3A 0.062(4) 0.020(3) 0.030(3) 0.002(2) 0.016(3) 0.001(2) C2A 0.060(4) 0.023(3) 0.029(3) 0.001(2) 0.017(2) -0.004(2) loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Ir Ir Uani 0.66312(2) 0.31524(1) 0.27185(1) 1.000 0.0182(1) . . I I Uani 0.80279(4) 0.21858(2) 0.11643(3) 1.000 0.0293(1) . . N1 N Uani 0.6852(6) 0.1676(3) 0.4329(3) 1.000 0.0252(12) . . N2 N Uani 0.4351(6) 0.1635(3) 0.3364(3) 1.000 0.0263(12) . . N3 N Uani 0.4414(7) 0.0945(3) 0.4050(4) 0.58(5) 0.0368(19) . . C1 C Uani 0.5870(7) 0.2105(3) 0.3520(4) 1.000 0.0245(14) . . C2 C Uani 0.5984(8) 0.0968(3) 0.4646(4) 0.58(5) 0.0368(19) . . C3 C Uani 0.2823(8) 0.1811(4) 0.2566(5) 1.000 0.0387(19) . . C4 C Uani 0.8662(8) 0.1902(3) 0.4805(5) 1.000 0.0320(17) . . C5 C Uani 0.4614(6) 0.3879(3) 0.3461(4) 1.000 0.0231(12) . . C6 C Uani 0.6226(7) 0.3913(3) 0.4155(4) 1.000 0.0242(14) . . C7 C Uani 0.7453(8) 0.4677(4) 0.4252(4) 1.000 0.0324(17) . . C8 C Uani 0.8965(7) 0.4642(4) 0.3419(4) 1.000 0.0334(17) . . C9 C Uani 0.8429(6) 0.4187(3) 0.2333(4) 1.000 0.0234(14) . . C10 C Uani 0.6816(6) 0.4300(3) 0.1684(4) 1.000 0.0232(14) . . C11 C Uani 0.5382(7) 0.4921(3) 0.1938(4) 1.000 0.0300(17) . . C12 C Uani 0.3910(7) 0.4564(4) 0.2678(4) 1.000 0.0341(17) . . N3A N Uani 0.5984(8) 0.0968(3) 0.4646(4) 0.42(5) 0.0368(19) . . C2A C Uani 0.4414(7) 0.0945(3) 0.4050(4) 0.42(5) 0.0368(19) . . H21 H Uiso 0.64260 0.05700 0.51910 0.58(5) 0.0440 calc R H33 H Uiso 0.24370 0.23910 0.26550 1.000 0.0580 calc R H31 H Uiso 0.18110 0.14370 0.27150 1.000 0.0580 calc R H32 H Uiso 0.31900 0.17230 0.17890 1.000 0.0580 calc R H43 H Uiso 0.95840 0.15920 0.44120 1.000 0.0480 calc R H51 H Uiso 0.39140 0.33810 0.34840 1.000 0.0280 . R H61 H Uiso 0.65620 0.34340 0.45940 1.000 0.0290 . R H71 H Uiso 0.80030 0.47160 0.50360 1.000 0.0390 calc R H72 H Uiso 0.67130 0.51850 0.41010 1.000 0.0390 calc R H81 H Uiso 0.93250 0.52190 0.32320 1.000 0.0400 calc R H82 H Uiso 1.00390 0.43630 0.37930 1.000 0.0400 calc R H91 H Uiso 0.92670 0.37920 0.20670 1.000 0.0280 . R H101 H Uiso 0.66020 0.39550 0.10350 1.000 0.0280 . R H111 H Uiso 0.47950 0.51240 0.12140 1.000 0.0360 calc R H112 H Uiso 0.59650 0.54050 0.23330 1.000 0.0360 calc R H121 H Uiso 0.34220 0.50200 0.31380 1.000 0.0410 calc R H122 H Uiso 0.28970 0.43430 0.21780 1.000 0.0410 calc R H41 H Uiso 0.87590 0.17640 0.56160 1.000 0.0480 calc R H42 H Uiso 0.88540 0.25020 0.47080 1.000 0.0480 calc R H21A H Uiso 0.35010 0.05290 0.40900 0.42(5) 0.0440 calc R loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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 _geom_angle_publ_flag I Ir C1 88.13(14) yes I Ir C5 156.44(13) yes I Ir C6 164.84(14) yes I Ir C9 92.04(12) yes I Ir C10 93.76(12) yes C1 Ir C5 92.48(19) yes C1 Ir C6 92.75(19) yes C1 Ir C9 156.16(19) yes C1 Ir C10 166.98(18) yes C5 Ir C6 38.68(19) yes C5 Ir C9 96.70(18) yes C5 Ir C10 80.68(17) yes C6 Ir C9 81.09(18) yes C6 Ir C10 88.80(18) yes C9 Ir C10 36.74(17) yes C1 N1 C2 112.1(4) yes C1 N1 C4 125.7(4) yes N3A N1 C1 112.1(4) yes C2 N1 C4 122.1(4) yes N3A N1 C4 122.1(4) yes N3 N2 C1 111.7(4) yes N3 N2 C3 122.6(5) yes C1 N2 C3 125.7(5) yes C1 N2 C2A 111.7(4) yes C2A N2 C3 122.6(5) yes N2 N3 C2 106.9(4) yes N1 N3A C2A 106.7(4) yes Ir C1 N1 127.0(4) yes Ir C1 N2 130.4(4) yes N1 C1 N2 102.6(4) yes N1 C2 N3 106.7(4) yes N2 C2A N3A 106.9(4) yes Ir C5 C6 70.9(3) yes C6 C5 C12 125.4(4) no Ir C5 C12 111.8(3) yes Ir C6 C7 114.3(3) yes C5 C6 C7 123.6(4) no Ir C6 C5 70.4(3) yes C6 C7 C8 111.9(5) no C7 C8 C9 113.6(4) no Ir C9 C8 108.8(3) yes C8 C9 C10 125.5(4) no Ir C9 C10 72.8(3) yes Ir C10 C11 112.1(3) yes Ir C10 C9 70.5(3) yes C9 C10 C11 124.7(4) no C10 C11 C12 113.3(4) no C5 C12 C11 112.9(4) no N1 C2 H21 126.59 no N3 C2 H21 126.73 no N3A C2A H21A 126.47 no N2 C2A H21A 126.58 no N2 C3 H32 109.45 no N2 C3 H33 109.49 no H31 C3 H33 109.44 no H32 C3 H33 109.51 no H31 C3 H32 109.45 no N2 C3 H31 109.49 no N1 C4 H43 109.52 no H41 C4 H42 109.42 no H41 C4 H43 109.51 no H42 C4 H43 109.51 no N1 C4 H41 109.42 no N1 C4 H42 109.44 no Ir C5 H51 86.82 no C12 C5 H51 117.43 no C6 C5 H51 117.22 no C7 C6 H61 118.28 no C5 C6 H61 118.11 no Ir C6 H61 85.82 no C6 C7 H71 109.28 no C8 C7 H72 109.17 no C6 C7 H72 109.25 no C8 C7 H71 109.21 no H71 C7 H72 107.91 no C7 C8 H82 108.84 no C9 C8 H81 108.83 no H81 C8 H82 107.69 no C9 C8 H82 108.90 no C7 C8 H81 108.86 no Ir C9 H91 88.62 no C10 C9 H91 117.16 no C8 C9 H91 117.39 no C9 C10 H101 117.76 no C11 C10 H101 117.57 no Ir C10 H101 87.03 no C12 C11 H111 108.93 no C10 C11 H111 108.94 no C10 C11 H112 108.90 no H111 C11 H112 107.74 no C12 C11 H112 108.93 no C5 C12 H122 109.00 no C5 C12 H121 108.94 no H121 C12 H122 107.82 no C11 C12 H121 109.02 no C11 C12 H122 109.03 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Ir I 2.6524(4) yes Ir C1 2.021(5) yes Ir C5 2.116(5) yes Ir C6 2.122(5) yes Ir C9 2.186(5) yes Ir C10 2.216(5) yes N1 C1 1.352(6) yes N1 C2 1.365(7) yes N1 C4 1.462(7) yes N1 N3A 1.365(7) yes N2 N3 1.369(6) yes N2 C1 1.352(7) yes N2 C3 1.453(7) yes N2 C2A 1.369(6) yes N3 C2 1.319(8) yes N3A C2A 1.319(8) yes C5 C6 1.404(7) no C5 C12 1.507(7) no C6 C7 1.522(8) no C7 C8 1.528(7) no C8 C9 1.507(7) no C9 C10 1.387(6) no C10 C11 1.494(7) no C11 C12 1.540(7) no C2 H21 0.9497 no C2A H21A 0.9499 no C3 H32 0.9806 no C3 H33 0.9793 no C3 H31 0.9800 no C4 H42 0.9795 no C4 H43 0.9792 no C4 H41 0.9805 no C5 H51 0.9513 no C6 H61 0.9507 no C7 H72 0.9900 no C7 H71 0.9900 no C8 H81 0.9903 no C8 H82 0.9899 no C9 H91 0.9498 no C10 H101 0.9501 no C11 H111 0.9897 no C11 H112 0.9899 no C12 H121 0.9899 no C12 H122 0.9895 no