#------------------------------------------------------------------------------ #$Date: 2015-01-23 14:30:19 +0200 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/07/51/4075163.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_4075163 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 'C11 H18 I N4 Rh' _chemical_formula_sum 'C11 H18 I N4 Rh' _chemical_formula_weight 436.10 _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 95.7301(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.4133(1) _cell_length_b 16.1728(1) _cell_length_c 11.6507(1) _cell_measurement_reflns_used 2634 _cell_measurement_temperature 123(1) _cell_measurement_theta_max 25.32 _cell_measurement_theta_min 2.16 _cell_volume 1389.87(2) _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 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 0.044 _diffrn_reflns_av_sigmaI/netI 0.0114 _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 30447 _diffrn_reflns_theta_full 25.32 _diffrn_reflns_theta_max 25.32 _diffrn_reflns_theta_min 2.16 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 3.435 _exptl_absorpt_correction_T_max 0.455 _exptl_absorpt_correction_T_min 0.265 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(applied during the scaling procedure; Nonius, 2001b)' _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 2.084 _exptl_crystal_density_meas ? _exptl_crystal_density_method none _exptl_crystal_description fragment _exptl_crystal_F_000 840 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.23 _refine_diff_density_max 0.529 _refine_diff_density_min -0.578 _refine_diff_density_rms 0.085 _refine_ls_extinction_coef 0.00388(18) _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 1.218 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 157 _refine_ls_number_reflns 2525 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.218 _refine_ls_R_factor_all 0.0192 _refine_ls_R_factor_gt 0.0190 _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^)+(0.0166P)^2^+3.1383P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.0479 _reflns_number_gt 2502 _reflns_number_total 2525 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file om0600801si20060125_122935.cif _[local]_cod_data_source_block JSCH-4381-123 _[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 4075163 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 I 0.0257(1) 0.0154(1) 0.0172(1) -0.0041(1) 0.0028(1) 0.0036(1) Rh 0.0124(1) 0.0110(1) 0.0123(1) -0.0008(1) 0.0024(1) -0.0009(1) N1 0.0255(14) 0.0166(13) 0.0157(12) 0.0017(10) 0.0026(10) 0.0012(11) N2 0.0210(14) 0.0211(14) 0.0187(13) 0.0007(11) 0.0022(11) -0.0089(11) N3 0.0379(17) 0.0223(15) 0.0270(15) 0.0002(12) 0.0080(13) -0.0140(13) N4 0.0418(17) 0.0171(14) 0.0258(15) 0.0027(11) 0.0091(13) -0.0038(12) C1 0.0182(14) 0.0141(14) 0.0132(14) -0.0036(11) 0.0035(11) -0.0010(11) C2 0.0212(17) 0.041(2) 0.0299(19) 0.0029(16) -0.0040(14) -0.0096(15) C3 0.0249(17) 0.038(2) 0.0295(19) 0.0039(16) -0.0017(14) 0.0110(15) C4 0.0208(15) 0.0146(14) 0.0197(15) -0.0034(12) 0.0107(12) -0.0026(12) C5 0.0275(16) 0.0121(14) 0.0150(14) -0.0023(11) 0.0063(12) -0.0006(12) C6 0.0279(17) 0.0196(16) 0.0180(15) -0.0053(12) 0.0009(13) -0.0056(13) C7 0.0178(15) 0.0224(16) 0.0240(16) -0.0031(13) 0.0003(12) -0.0046(12) C8 0.0164(14) 0.0145(14) 0.0191(15) -0.0008(11) 0.0063(11) -0.0023(11) C9 0.0196(15) 0.0127(14) 0.0158(14) -0.0003(11) 0.0064(11) -0.0023(11) C10 0.0215(15) 0.0164(15) 0.0229(16) 0.0043(12) 0.0041(12) 0.0013(12) C11 0.0219(16) 0.0194(16) 0.0292(17) 0.0002(13) 0.0084(13) 0.0058(13) 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 I I Uani 0.69183(3) 0.20663(1) 0.10995(2) 1.000 0.0194(1) . . Rh Rh Uani 0.61501(3) 0.31275(1) 0.27441(2) 1.000 0.0118(1) . . N1 N Uani 0.5872(4) 0.16255(16) 0.4269(2) 1.000 0.0192(8) . . N2 N Uani 0.3370(4) 0.18546(16) 0.3368(2) 1.000 0.0203(8) . . N3 N Uani 0.3201(4) 0.11607(18) 0.4020(2) 1.000 0.0288(9) . . N4 N Uani 0.4739(4) 0.10189(17) 0.4570(2) 1.000 0.0279(9) . . C1 C Uani 0.5052(4) 0.21623(18) 0.3508(2) 1.000 0.0150(8) . . C2 C Uani 0.1806(5) 0.2171(2) 0.2664(3) 1.000 0.0311(11) . . C3 C Uani 0.7777(5) 0.1614(2) 0.4739(3) 1.000 0.0311(11) . . C4 C Uani 0.4564(4) 0.39634(18) 0.3620(3) 1.000 0.0178(8) . . C5 C Uani 0.6251(4) 0.38739(18) 0.4264(3) 1.000 0.0179(8) . . C6 C Uani 0.7749(4) 0.4519(2) 0.4328(3) 1.000 0.0219(9) . . C7 C Uani 0.9067(4) 0.4405(2) 0.3402(3) 1.000 0.0215(9) . . C8 C Uani 0.8211(4) 0.40268(18) 0.2297(3) 1.000 0.0164(8) . . C9 C Uani 0.6590(4) 0.42584(18) 0.1720(2) 1.000 0.0157(8) . . C10 C Uani 0.5441(4) 0.49687(19) 0.2091(3) 1.000 0.0201(9) . . C11 C Uani 0.3987(4) 0.4686(2) 0.2854(3) 1.000 0.0231(9) . . H21 H Uiso 0.11290 0.17100 0.22830 1.000 0.0470 calc R H22 H Uiso 0.22040 0.25470 0.20790 1.000 0.0470 calc R H23 H Uiso 0.10230 0.24700 0.31520 1.000 0.0470 calc R H31 H Uiso 0.79200 0.12570 0.54220 1.000 0.0460 calc R H32 H Uiso 0.81660 0.21770 0.49560 1.000 0.0460 calc R H33 H Uiso 0.85210 0.14020 0.41550 1.000 0.0460 calc R H41 H Uiso 0.37080 0.35310 0.36710 1.000 0.0210 calc R H51 H Uiso 0.64750 0.33770 0.46890 1.000 0.0210 calc R H61 H Uiso 0.84410 0.44920 0.50990 1.000 0.0260 calc R H62 H Uiso 0.71940 0.50750 0.42420 1.000 0.0260 calc R H71 H Uiso 0.95770 0.49510 0.32260 1.000 0.0260 calc R H72 H Uiso 1.00840 0.40490 0.37190 1.000 0.0260 calc R H81 H Uiso 0.88510 0.35900 0.19730 1.000 0.0200 calc R H91 H Uiso 0.61590 0.39570 0.10490 1.000 0.0190 calc R H101 H Uiso 0.48450 0.52450 0.13950 1.000 0.0240 calc R H102 H Uiso 0.62390 0.53790 0.25190 1.000 0.0240 calc R H111 H Uiso 0.36760 0.51560 0.33430 1.000 0.0280 calc R H112 H Uiso 0.28800 0.45320 0.23540 1.000 0.0280 calc R loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 Rh C1 86.76(7) yes I Rh C4 157.22(9) yes I Rh C5 164.33(8) yes I Rh C8 92.97(8) yes I Rh C9 95.17(7) yes C1 Rh C4 90.77(12) yes C1 Rh C5 93.10(11) yes C1 Rh C8 159.46(12) yes C1 Rh C9 164.50(11) yes C4 Rh C5 38.40(12) yes C4 Rh C8 97.10(11) yes C4 Rh C9 81.49(11) yes C5 Rh C8 81.71(12) yes C5 Rh C9 89.15(11) yes C8 Rh C9 35.97(11) yes N4 N1 C1 112.7(3) yes N4 N1 C3 119.5(2) yes C1 N1 C3 127.7(3) yes N3 N2 C1 111.9(3) yes N3 N2 C2 119.5(3) yes C1 N2 C2 128.5(3) yes N2 N3 N4 107.5(3) yes N1 N4 N3 106.6(2) yes Rh C1 N1 128.2(2) yes Rh C1 N2 130.5(2) yes N1 C1 N2 101.3(2) yes Rh C4 C5 71.54(18) yes Rh C4 C11 110.4(2) yes C5 C4 C11 125.7(3) no Rh C5 C4 70.07(19) yes Rh C5 C6 113.2(2) yes C4 C5 C6 124.4(3) no C5 C6 C7 113.3(3) no C6 C7 C8 113.9(3) no Rh C8 C7 107.9(2) yes Rh C8 C9 72.67(17) yes C7 C8 C9 125.6(3) no Rh C9 C8 71.36(17) yes Rh C9 C10 110.66(19) yes C8 C9 C10 123.9(3) no C9 C10 C11 112.7(3) no C4 C11 C10 113.6(3) no N2 C2 H21 109.47 no N2 C2 H22 109.51 no N2 C2 H23 109.49 no H21 C2 H22 109.45 no H21 C2 H23 109.39 no H22 C2 H23 109.52 no N1 C3 H31 109.48 no N1 C3 H32 109.44 no N1 C3 H33 109.51 no H31 C3 H32 109.42 no H31 C3 H33 109.57 no H32 C3 H33 109.43 no Rh C4 H41 88.09 no C5 C4 H41 117.18 no C11 C4 H41 117.14 no Rh C5 H51 86.78 no C4 C5 H51 117.85 no C6 C5 H51 117.79 no C5 C6 H61 108.91 no C5 C6 H62 108.92 no C7 C6 H61 108.87 no C7 C6 H62 108.96 no H61 C6 H62 107.73 no C6 C7 H71 108.72 no C6 C7 H72 108.76 no C8 C7 H71 108.78 no C8 C7 H72 108.82 no H71 C7 H72 107.67 no Rh C8 H81 89.35 no C7 C8 H81 117.19 no C9 C8 H81 117.19 no Rh C9 H91 87.95 no C8 C9 H91 118.07 no C10 C9 H91 118.08 no C9 C10 H101 108.99 no C9 C10 H102 109.06 no C11 C10 H101 109.10 no C11 C10 H102 109.09 no H101 C10 H102 107.78 no C4 C11 H111 108.85 no C4 C11 H112 108.86 no C10 C11 H111 108.78 no C10 C11 H112 108.86 no H111 C11 H112 107.74 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag I Rh 2.6757(3) yes Rh C1 2.009(3) yes Rh C4 2.119(3) yes Rh C5 2.138(3) yes Rh C8 2.209(3) yes Rh C9 2.226(3) yes N1 N4 1.360(4) yes N1 C1 1.342(4) yes N1 C3 1.463(5) yes N2 N3 1.368(4) yes N2 C1 1.337(4) yes N2 C2 1.445(5) yes N3 N4 1.272(4) yes C4 C5 1.400(4) no C4 C11 1.506(5) no C5 C6 1.520(4) no C6 C7 1.537(5) no C7 C8 1.507(5) no C8 C9 1.369(4) no C9 C10 1.518(4) no C10 C11 1.534(4) no C2 H21 0.9800 no C2 H22 0.9806 no C2 H23 0.9798 no C3 H31 0.9803 no C3 H32 0.9806 no C3 H33 0.9796 no C4 H41 0.9502 no C5 H51 0.9498 no C6 H61 0.9899 no C6 H62 0.9898 no C7 H71 0.9901 no C7 H72 0.9903 no C8 H81 0.9499 no C9 H91 0.9492 no C10 H101 0.9904 no C10 H102 0.9900 no C11 H111 0.9908 no C11 H112 0.9896 no