#------------------------------------------------------------------------------ #$Date: 2015-01-23 14:30:19 +0200 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/07/51/4075162.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_4075162 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 'C17 H24 I N4 O2 Rh' _chemical_formula_sum 'C17 H24 I N4 O2 Rh' _chemical_formula_weight 546.21 _chemical_name_systematic ; ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 95.6384(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.5467(1) _cell_length_b 12.0211(1) _cell_length_c 13.7354(1) _cell_measurement_reflns_used 3672 _cell_measurement_temperature 123(1) _cell_measurement_theta_max 25.38 _cell_measurement_theta_min 1.77 _cell_volume 1897.30(3) _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 0.051 _diffrn_reflns_av_sigmaI/netI 0.0139 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 44339 _diffrn_reflns_theta_full 25.38 _diffrn_reflns_theta_max 25.38 _diffrn_reflns_theta_min 1.77 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 2.545 _exptl_absorpt_correction_T_max 0.626 _exptl_absorpt_correction_T_min 0.305 _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 1.912 _exptl_crystal_density_meas ? _exptl_crystal_density_method none _exptl_crystal_description plate _exptl_crystal_F_000 1072 _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.536 _refine_diff_density_min -0.553 _refine_diff_density_rms 0.086 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 230 _refine_ls_number_reflns 3490 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.054 _refine_ls_R_factor_all 0.0245 _refine_ls_R_factor_gt 0.0225 _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^)+(0.0277P)^2^+4.1863P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.0569 _reflns_number_gt 3280 _reflns_number_total 3490 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file om0600801si20060125_122752.cif _[local]_cod_data_source_block JSCI-4386-123 _[local]_cod_cif_authors_sg_H-M 'P 21/c' _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 4075162 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z 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 0.0227(1) 0.0285(1) 0.0148(1) 0.0004(1) 0.0020(1) 0.0000(1) Rh 0.0208(1) 0.0226(1) 0.0124(1) -0.0016(1) 0.0032(1) 0.0033(1) O2 0.0334(14) 0.0621(18) 0.0322(14) 0.0040(12) 0.0158(11) 0.0119(12) O6 0.0460(14) 0.0289(13) 0.0302(13) -0.0095(10) 0.0023(11) 0.0049(11) N1 0.0282(14) 0.0370(15) 0.0173(12) -0.0005(11) 0.0031(10) 0.0146(12) N3 0.0208(13) 0.0351(15) 0.0215(13) 0.0038(11) 0.0044(10) 0.0051(11) N7 0.0210(12) 0.0233(13) 0.0157(12) -0.0005(10) 0.0031(9) 0.0036(10) N9 0.0204(13) 0.0239(13) 0.0153(12) -0.0009(10) 0.0023(10) 0.0020(10) C1 0.051(2) 0.046(2) 0.0220(17) -0.0016(15) 0.0082(15) 0.0243(18) C2 0.0265(17) 0.045(2) 0.0216(16) 0.0076(14) 0.0060(13) 0.0182(15) C3 0.0256(17) 0.045(2) 0.040(2) 0.0045(17) 0.0101(15) -0.0023(15) C4 0.0212(15) 0.0287(16) 0.0149(14) 0.0047(12) 0.0025(11) 0.0075(12) C5 0.0224(15) 0.0254(16) 0.0143(14) -0.0006(12) 0.0025(11) 0.0064(12) C6 0.0299(16) 0.0293(17) 0.0161(15) 0.0003(12) -0.0004(12) 0.0130(14) C7 0.0268(16) 0.0311(17) 0.0259(16) -0.0031(13) 0.0052(13) -0.0048(13) C8 0.0226(15) 0.0241(15) 0.0121(13) 0.0015(11) -0.0011(11) 0.0038(12) C9 0.0317(17) 0.0296(17) 0.0262(17) -0.0045(14) 0.0048(14) -0.0064(14) C10 0.0395(19) 0.0340(18) 0.0212(16) 0.0072(14) 0.0110(14) 0.0168(15) C11 0.0312(18) 0.053(2) 0.0255(17) 0.0098(16) -0.0009(14) 0.0105(17) C12 0.023(2) 0.186(7) 0.043(3) 0.044(3) -0.0054(18) -0.005(3) C13 0.0258(17) 0.050(2) 0.047(2) -0.0173(18) 0.0081(16) 0.0000(16) C14 0.0267(16) 0.0270(16) 0.0271(17) -0.0060(13) 0.0116(13) 0.0037(13) C15 0.0280(16) 0.0278(16) 0.0159(14) -0.0053(12) 0.0056(12) 0.0073(13) C16 0.061(2) 0.0269(18) 0.0264(18) -0.0040(14) 0.0025(16) 0.0033(17) C17 0.152(5) 0.034(2) 0.044(3) 0.0156(19) 0.055(3) 0.035(3) 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 0.25874(2) 0.14036(2) 0.33608(1) 1.000 0.0220(1) . . Rh Rh Uani 0.14853(2) 0.25922(2) 0.19070(2) 1.000 0.0185(1) . . O2 O Uani 0.5956(2) 0.1315(2) -0.17305(19) 1.000 0.0417(9) . . O6 O Uani 0.2902(2) -0.0833(2) -0.09829(17) 1.000 0.0351(8) . . N1 N Uani 0.4428(2) 0.0260(2) -0.13496(18) 1.000 0.0274(8) . . N3 N Uani 0.4973(2) 0.1907(2) -0.04691(19) 1.000 0.0257(8) . . N7 N Uani 0.2437(2) 0.0967(2) 0.05034(17) 1.000 0.0199(7) . . N9 N Uani 0.3572(2) 0.2400(2) 0.07270(17) 1.000 0.0198(7) . . C1 C Uani 0.4667(3) -0.0527(3) -0.2119(2) 1.000 0.0394(11) . . C2 C Uani 0.5166(3) 0.1171(3) -0.1218(2) 1.000 0.0308(10) . . C3 C Uani 0.5761(3) 0.2862(3) -0.0316(3) 1.000 0.0364(11) . . C4 C Uani 0.4023(3) 0.1737(3) 0.0039(2) 1.000 0.0216(9) . . C5 C Uani 0.3326(3) 0.0839(3) -0.0101(2) 1.000 0.0207(9) . . C6 C Uani 0.3485(3) 0.0007(3) -0.0818(2) 1.000 0.0253(9) . . C7 C Uani 0.1534(3) 0.0142(3) 0.0633(2) 1.000 0.0278(9) . . C8 C Uani 0.2564(3) 0.1925(2) 0.1002(2) 1.000 0.0198(8) . . C9 C Uani 0.4007(3) 0.3451(3) 0.1151(2) 1.000 0.0290(10) . . C10 C Uani 0.1031(3) 0.3881(3) 0.0877(2) 1.000 0.0310(10) . . C11 C Uani 0.0253(3) 0.3009(3) 0.0710(3) 1.000 0.0368(11) . . C12 C Uani -0.0971(4) 0.2999(7) 0.0993(3) 1.000 0.085(3) . . C13 C Uani -0.1130(3) 0.3048(3) 0.2032(3) 1.000 0.0406(11) . . C14 C Uani -0.0051(3) 0.2962(3) 0.2732(2) 1.000 0.0263(9) . . C15 C Uani 0.0748(3) 0.3796(3) 0.2904(2) 1.000 0.0237(9) . . C16 C Uani 0.0666(4) 0.4921(3) 0.2417(3) 1.000 0.0382(11) . . C17 C Uani 0.0739(6) 0.4949(4) 0.1368(3) 1.000 0.074(2) . . H11 H Uiso 0.44900 -0.12840 -0.19140 1.000 0.0590 calc R H12 H Uiso 0.54890 -0.04790 -0.22340 1.000 0.0590 calc R H13 H Uiso 0.41800 -0.03440 -0.27230 1.000 0.0590 calc R H31 H Uiso 0.64200 0.27660 -0.07070 1.000 0.0550 calc R H32 H Uiso 0.60480 0.29120 0.03780 1.000 0.0550 calc R H33 H Uiso 0.53420 0.35450 -0.05170 1.000 0.0550 calc R H71 H Uiso 0.11950 -0.01170 -0.00090 1.000 0.0420 calc R H72 H Uiso 0.09250 0.04810 0.09850 1.000 0.0420 calc R H73 H Uiso 0.18770 -0.04890 0.10090 1.000 0.0420 calc R H91 H Uiso 0.34940 0.37050 0.16340 1.000 0.0440 calc R H92 H Uiso 0.40220 0.40090 0.06330 1.000 0.0440 calc R H93 H Uiso 0.47950 0.33430 0.14720 1.000 0.0440 calc R H101 H Uiso 0.17880 0.38000 0.06710 1.000 0.0370 calc R H111 H Uiso 0.05130 0.23670 0.03910 1.000 0.0440 calc R H121 H Uiso -0.13900 0.36380 0.06680 1.000 0.1010 calc R H122 H Uiso -0.13550 0.23140 0.07220 1.000 0.1010 calc R H131 H Uiso -0.16640 0.24400 0.21800 1.000 0.0480 calc R H132 H Uiso -0.15210 0.37590 0.21590 1.000 0.0480 calc R H141 H Uiso 0.00860 0.22830 0.30790 1.000 0.0320 calc R H151 H Uiso 0.14020 0.36560 0.33630 1.000 0.0280 calc R H161 H Uiso -0.00820 0.52640 0.25500 1.000 0.0460 calc R H162 H Uiso 0.12960 0.53950 0.27330 1.000 0.0460 calc R H171 H Uiso 0.13330 0.55090 0.12350 1.000 0.0880 calc R H172 H Uiso -0.00170 0.52170 0.10520 1.000 0.0880 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' O O 0.0106 0.0060 '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 C8 88.30(8) yes I Rh C10 162.45(9) yes I Rh C11 159.53(10) yes I Rh C14 94.05(8) yes I Rh C15 94.07(8) yes C8 Rh C10 90.38(11) yes C8 Rh C11 91.38(13) yes C8 Rh C14 163.88(12) yes C8 Rh C15 160.07(12) yes C10 Rh C11 37.99(13) yes C10 Rh C14 92.07(12) yes C10 Rh C15 81.44(12) yes C11 Rh C14 80.88(13) yes C11 Rh C15 93.17(13) yes C14 Rh C15 35.70(13) yes C1 N1 C2 116.5(2) yes C1 N1 C6 116.5(3) yes C2 N1 C6 127.0(3) yes C2 N3 C3 117.5(3) yes C2 N3 C4 118.4(3) yes C3 N3 C4 124.0(3) yes C5 N7 C7 125.1(3) yes C5 N7 C8 110.5(3) yes C7 N7 C8 124.3(3) yes C4 N9 C8 109.5(2) yes C4 N9 C9 129.5(3) yes C8 N9 C9 121.0(2) yes O2 C2 N1 121.5(3) yes O2 C2 N3 121.4(3) yes N1 C2 N3 117.2(3) yes N3 C4 N9 129.6(3) yes N3 C4 C5 122.8(3) yes N9 C4 C5 107.5(3) yes N7 C5 C4 106.9(3) yes N7 C5 C6 129.9(3) yes C4 C5 C6 122.9(3) no O6 C6 N1 121.6(3) yes O6 C6 C5 126.9(3) yes N1 C6 C5 111.5(3) yes Rh C8 N7 128.0(2) yes Rh C8 N9 126.41(18) yes N7 C8 N9 105.6(2) yes Rh C10 C11 70.9(2) yes Rh C10 C17 112.0(2) yes C11 C10 C17 123.4(4) no Rh C11 C10 71.1(2) yes Rh C11 C12 111.9(3) yes C10 C11 C12 125.1(4) no C11 C12 C13 117.7(4) no C12 C13 C14 116.6(3) no Rh C14 C13 109.8(2) yes Rh C14 C15 71.3(2) yes C13 C14 C15 124.3(3) no Rh C15 C14 73.1(2) yes Rh C15 C16 108.8(2) yes C14 C15 C16 124.7(3) no C15 C16 C17 117.0(3) no C10 C17 C16 117.6(4) no N1 C1 H11 109.45 no N1 C1 H12 109.43 no N1 C1 H13 109.42 no H11 C1 H12 109.51 no H11 C1 H13 109.45 no H12 C1 H13 109.56 no N3 C3 H31 109.46 no N3 C3 H32 109.46 no N3 C3 H33 109.48 no H31 C3 H32 109.49 no H31 C3 H33 109.45 no H32 C3 H33 109.48 no N7 C7 H71 109.42 no N7 C7 H72 109.43 no N7 C7 H73 109.47 no H71 C7 H72 109.48 no H71 C7 H73 109.49 no H72 C7 H73 109.54 no N9 C9 H91 109.42 no N9 C9 H92 109.45 no N9 C9 H93 109.44 no H91 C9 H92 109.47 no H91 C9 H93 109.44 no H92 C9 H93 109.62 no Rh C10 H101 87.10 no C11 C10 H101 118.30 no C17 C10 H101 118.33 no Rh C11 H111 86.99 no C10 C11 H111 117.50 no C12 C11 H111 117.42 no C11 C12 H121 107.91 no C11 C12 H122 107.89 no C13 C12 H121 107.88 no C13 C12 H122 107.86 no H121 C12 H122 107.14 no C12 C13 H131 108.18 no C12 C13 H132 108.11 no C14 C13 H131 108.19 no C14 C13 H132 108.11 no H131 C13 H132 107.28 no Rh C14 H141 88.98 no C13 C14 H141 117.85 no C15 C14 H141 117.83 no Rh C15 H151 88.04 no C14 C15 H151 117.62 no C16 C15 H151 117.68 no C15 C16 H161 108.03 no C15 C16 H162 108.08 no C17 C16 H161 108.07 no C17 C16 H162 108.05 no H161 C16 H162 107.22 no C10 C17 H171 107.92 no C10 C17 H172 107.95 no C16 C17 H171 107.91 no C16 C17 H172 107.94 no H171 C17 H172 107.14 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag I Rh 2.6738(3) yes Rh C8 2.011(3) yes Rh C10 2.129(3) yes Rh C11 2.126(4) yes Rh C14 2.241(3) yes Rh C15 2.219(3) yes O2 C2 1.218(4) yes O6 C6 1.222(4) yes N1 C1 1.465(4) yes N1 C2 1.389(4) yes N1 C6 1.403(4) yes N3 C2 1.391(4) yes N3 C3 1.467(4) yes N3 C4 1.372(4) yes N7 C5 1.391(4) yes N7 C7 1.463(4) yes N7 C8 1.341(3) yes N9 C4 1.377(4) yes N9 C8 1.382(4) yes N9 C9 1.460(4) yes C4 C5 1.349(5) no C5 C6 1.428(5) no C10 C11 1.385(5) no C10 C17 1.504(6) no C11 C12 1.502(6) no C12 C13 1.458(6) no C13 C14 1.501(5) no C14 C15 1.367(5) no C15 C16 1.508(5) no C16 C17 1.452(6) no C1 H11 0.9800 no C1 H12 0.9791 no C1 H13 0.9804 no C3 H31 0.9803 no C3 H32 0.9798 no C3 H33 0.9789 no C7 H71 0.9798 no C7 H72 0.9804 no C7 H73 0.9792 no C9 H91 0.9805 no C9 H92 0.9792 no C9 H93 0.9800 no C10 H101 0.9498 no C11 H111 0.9506 no C12 H121 0.9904 no C12 H122 0.9903 no C13 H131 0.9901 no C13 H132 0.9901 no C14 H141 0.9506 no C15 H151 0.9500 no C16 H161 0.9901 no C16 H162 0.9900 no C17 H171 0.9908 no C17 H172 0.9898 no