#------------------------------------------------------------------------------ #$Date: 2014-07-11 21:33:45 +0300 (Fri, 11 Jul 2014) $ #$Revision: 120075 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/07/51/4075183.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_4075183 loop_ _publ_author_name 'Herrmann, Wolfgang A.' 'Baskakov, Denys' 'Herdtweck, Eberhardt' 'Hoffmann, Stephan D.' 'Bunlaksananusorn, Tanasri' 'Rampf, Florian' 'Rodefeld, Lars' _publ_section_title ; Chiral N-Heterocyclic Carbene Ligands Derived from 2,2‘-Bipiperidine and Partially Reduced Biisoquinoline:  Rhodium and Iridium Complexes in Asymmetric Catalysis† ; _journal_issue 10 _journal_name_full Organometallics _journal_page_first 2449 _journal_volume 25 _journal_year 2006 _chemical_absolute_configuration ad _chemical_formula_moiety 'C19 H30 Cl N2 Rh' _chemical_formula_sum 'C19 H30 Cl N2 Rh' _chemical_formula_weight 424.81 _chemical_name_systematic ; ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 19 _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.6567(1) _cell_length_b 11.3869(1) _cell_length_c 15.1128(1) _cell_measurement_reflns_used 1942 _cell_measurement_temperature 173(1) _cell_measurement_theta_max 25.31 _cell_measurement_theta_min 2.24 _cell_volume 1833.89(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 173(1) _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 18 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 0.037 _diffrn_reflns_av_sigmaI/netI 0.0125 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 40406 _diffrn_reflns_theta_full 25.31 _diffrn_reflns_theta_max 25.31 _diffrn_reflns_theta_min 2.24 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 1.078 _exptl_absorpt_correction_T_max 0.645 _exptl_absorpt_correction_T_min 0.498 _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 1.539 _exptl_crystal_density_meas none _exptl_crystal_density_method none _exptl_crystal_description fragment _exptl_crystal_F_000 880 _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.56 _exptl_crystal_size_min 0.41 _refine_diff_density_max 0.302 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.042 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(2) _refine_ls_extinction_coef 0.0060(2) _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 1.082 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 3348 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.082 _refine_ls_R_factor_all 0.0161 _refine_ls_R_factor_gt 0.0157 _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^)+(0.0165P)^2^+0.9785P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0383 _reflns_number_gt 3314 _reflns_number_total 3348 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file om060098bsi20060201_054447.cif _[local]_cod_data_source_block BASC-4456-173 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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 ; _cod_database_code 4075183 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,-y,1/2+z 1/2+x,1/2-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 Rh 0.0150(1) 0.0177(1) 0.0247(1) 0.0014(1) -0.0016(1) -0.0007(1) Cl 0.0298(3) 0.0306(3) 0.0703(4) 0.0254(3) 0.0023(3) 0.0006(2) N1 0.0179(9) 0.0241(9) 0.0278(10) 0.0011(7) 0.0016(7) 0.0008(7) N2 0.0157(9) 0.0367(11) 0.0290(10) -0.0066(9) -0.0003(8) -0.0003(8) C1 0.0209(10) 0.0165(9) 0.0274(10) 0.0063(9) 0.0041(7) -0.0008(9) C2 0.0343(14) 0.0327(13) 0.0340(13) -0.0080(11) 0.0038(11) -0.0011(11) C3 0.0515(16) 0.0380(14) 0.0297(13) -0.0027(11) 0.0089(12) 0.0038(12) C4 0.0472(14) 0.0395(13) 0.0456(14) 0.0086(13) 0.0253(12) -0.0011(13) C5 0.0279(12) 0.0344(13) 0.0470(15) 0.0091(11) 0.0078(11) -0.0052(10) C6 0.0149(9) 0.0227(10) 0.0386(11) 0.0082(11) -0.0003(9) 0.0030(8) C7 0.0166(10) 0.0281(12) 0.0330(12) 0.0060(10) -0.0056(10) 0.0016(9) C8 0.0275(13) 0.0340(14) 0.0619(17) -0.0069(12) 0.0007(13) -0.0073(11) C9 0.0357(14) 0.0402(15) 0.0638(18) -0.0185(14) -0.0055(13) -0.0061(13) C10 0.0353(14) 0.0360(13) 0.0420(14) -0.0083(12) -0.0032(11) 0.0067(11) C11 0.0239(11) 0.0459(13) 0.0294(11) -0.0097(12) -0.0011(9) 0.0003(12) C12 0.0223(11) 0.0202(10) 0.0364(12) 0.0053(8) -0.0001(9) -0.0007(9) C13 0.0270(11) 0.0263(11) 0.0297(11) 0.0056(9) 0.0020(9) -0.0024(9) C14 0.0386(15) 0.0459(15) 0.0414(15) 0.0113(12) 0.0139(12) 0.0069(12) C15 0.0295(13) 0.0648(19) 0.0412(14) 0.0046(15) 0.0082(11) 0.0103(14) C16 0.0147(10) 0.0327(12) 0.0415(14) 0.0017(11) -0.0029(11) 0.0050(8) C17 0.0197(10) 0.0339(14) 0.0343(12) 0.0057(10) -0.0102(9) -0.0013(9) C18 0.0397(15) 0.0399(15) 0.0526(16) -0.0032(13) -0.0173(13) -0.0100(12) C19 0.0452(15) 0.0250(12) 0.0534(16) -0.0039(11) -0.0103(12) -0.0044(11) 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 Rh Rh Uani 0.28606(1) 0.56287(1) 0.13760(1) 1.000 0.0191(1) . . Cl Cl Uani 0.24211(5) 0.40005(5) 0.23015(5) 1.000 0.0436(2) . . N1 N Uani 0.01038(16) 0.61142(16) 0.15431(12) 1.000 0.0233(5) . . N2 N Uani 0.05104(17) 0.49939(18) 0.04272(13) 1.000 0.0271(6) . . C1 C Uani 0.10271(18) 0.5613(2) 0.10873(13) 1.000 0.0216(6) . . C2 C Uani 0.0242(2) 0.6736(2) 0.23798(16) 1.000 0.0337(8) . . C3 C Uani -0.0305(3) 0.6009(2) 0.31305(16) 1.000 0.0397(8) . . C4 C Uani -0.1645(2) 0.5630(3) 0.29119(17) 1.000 0.0441(8) . . C5 C Uani -0.1678(2) 0.4939(2) 0.20478(17) 1.000 0.0364(8) . . C6 C Uani -0.11547(17) 0.56774(19) 0.12921(15) 1.000 0.0254(6) . . C7 C Uani -0.0871(2) 0.5041(2) 0.04185(16) 1.000 0.0259(7) . . C8 C Uani -0.1392(2) 0.3809(2) 0.0270(2) 1.000 0.0411(9) . . C9 C Uani -0.0785(3) 0.3234(3) -0.0532(2) 1.000 0.0466(9) . . C10 C Uani 0.0640(2) 0.3181(2) -0.04256(18) 1.000 0.0378(8) . . C11 C Uani 0.1181(2) 0.4396(2) -0.02818(14) 1.000 0.0331(7) . . C12 C Uani 0.3057(2) 0.74243(18) 0.10784(14) 1.000 0.0263(6) . . C13 C Uani 0.3330(2) 0.6772(2) 0.03147(15) 1.000 0.0277(6) . . C14 C Uani 0.4640(3) 0.6564(3) -0.00392(18) 1.000 0.0420(9) . . C15 C Uani 0.5294(2) 0.5502(3) 0.03583(17) 1.000 0.0452(9) . . C16 C Uani 0.48663(19) 0.5175(2) 0.12762(17) 1.000 0.0296(7) . . C17 C Uani 0.4750(2) 0.5905(2) 0.19802(16) 1.000 0.0293(7) . . C18 C Uani 0.5089(3) 0.7186(2) 0.1943(2) 1.000 0.0441(9) . . C19 C Uani 0.3996(3) 0.7963(2) 0.17101(18) 1.000 0.0412(8) . . H16 H Uiso -0.17250 0.63580 0.11770 1.000 0.0300 calc R H21 H Uiso -0.01960 0.75010 0.23470 1.000 0.0400 calc R H22 H Uiso 0.11420 0.68890 0.24950 1.000 0.0400 calc R H31 H Uiso -0.03050 0.64770 0.36820 1.000 0.0480 calc R H32 H Uiso 0.02230 0.53050 0.32280 1.000 0.0480 calc R H41 H Uiso -0.19770 0.51360 0.33980 1.000 0.0530 calc R H42 H Uiso -0.21860 0.63330 0.28590 1.000 0.0530 calc R H51 H Uiso -0.11750 0.42130 0.21110 1.000 0.0440 calc R H52 H Uiso -0.25540 0.47100 0.19120 1.000 0.0440 calc R H71 H Uiso -0.11440 0.55530 -0.00830 1.000 0.0310 calc R H81 H Uiso -0.12320 0.33230 0.08020 1.000 0.0490 calc R H82 H Uiso -0.23110 0.38540 0.01800 1.000 0.0490 calc R H91 H Uiso -0.09970 0.36880 -0.10700 1.000 0.0560 calc R H92 H Uiso -0.11200 0.24290 -0.06050 1.000 0.0560 calc R H101 H Uiso 0.08540 0.26750 0.00850 1.000 0.0450 calc R H102 H Uiso 0.10170 0.28290 -0.09620 1.000 0.0450 calc R H111 H Uiso 0.20810 0.43330 -0.01270 1.000 0.0400 calc R H112 H Uiso 0.11110 0.48580 -0.08350 1.000 0.0400 calc R H121 H Uiso 0.21950 0.75400 0.12130 1.000 0.0320 calc R H131 H Uiso 0.26470 0.64380 -0.00020 1.000 0.0330 calc R H141 H Uiso 0.51560 0.72700 0.00780 1.000 0.0500 calc R H142 H Uiso 0.45920 0.64610 -0.06890 1.000 0.0500 calc R H151 H Uiso 0.51580 0.48210 -0.00370 1.000 0.0540 calc R H152 H Uiso 0.62080 0.56590 0.03760 1.000 0.0540 calc R H161 H Uiso 0.46560 0.43740 0.13710 1.000 0.0360 calc R H171 H Uiso 0.44400 0.55940 0.25210 1.000 0.0350 calc R H181 H Uiso 0.57610 0.72980 0.14990 1.000 0.0530 calc R H182 H Uiso 0.54260 0.74280 0.25260 1.000 0.0530 calc R H191 H Uiso 0.43240 0.86950 0.14430 1.000 0.0490 calc R H192 H Uiso 0.35540 0.81800 0.22620 1.000 0.0490 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' Cl Cl 0.1484 0.1585 '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 Cl Rh C1 85.91(6) yes Cl Rh C12 155.01(6) yes Cl Rh C13 166.25(6) yes Cl Rh C16 92.79(6) yes Cl Rh C17 92.70(6) yes C1 Rh C12 93.39(9) yes C1 Rh C13 94.05(8) yes C1 Rh C16 158.34(9) yes C1 Rh C17 166.00(8) yes C12 Rh C13 38.74(8) yes C12 Rh C16 96.70(8) yes C12 Rh C17 82.00(8) yes C13 Rh C16 82.17(9) yes C13 Rh C17 90.58(8) yes C16 Rh C17 35.58(9) yes C1 N1 C2 125.69(17) yes C1 N1 C6 113.18(17) yes C2 N1 C6 118.52(17) yes C1 N2 C7 113.46(18) yes C1 N2 C11 126.29(18) yes C7 N2 C11 120.04(18) yes Rh C1 N1 127.26(15) yes Rh C1 N2 124.61(15) yes N1 C1 N2 107.90(17) yes N1 C2 C3 110.14(18) yes C2 C3 C4 110.5(2) no C3 C4 C5 110.64(19) no C4 C5 C6 110.4(2) no N1 C6 C5 108.97(17) yes N1 C6 C7 101.57(16) yes C5 C6 C7 117.12(19) no N2 C7 C6 101.90(17) yes N2 C7 C8 109.36(18) yes C6 C7 C8 119.3(2) no C7 C8 C9 111.0(2) no C8 C9 C10 110.8(2) no C9 C10 C11 110.9(2) no N2 C11 C10 110.23(18) yes Rh C12 C13 71.46(13) yes Rh C12 C19 108.96(14) yes C13 C12 C19 126.6(2) no Rh C13 C12 69.80(12) yes Rh C13 C14 112.82(17) yes C12 C13 C14 124.4(2) no C13 C14 C15 114.1(2) no C14 C15 C16 115.0(2) no Rh C16 C15 107.36(15) yes Rh C16 C17 73.38(13) yes C15 C16 C17 126.8(2) no Rh C17 C16 71.05(13) yes Rh C17 C18 109.75(17) yes C16 C17 C18 122.9(2) no C17 C18 C19 113.2(2) no C12 C19 C18 114.9(2) no N1 C2 H21 109.68 no N1 C2 H22 109.64 no C3 C2 H21 109.62 no C3 C2 H22 109.63 no H21 C2 H22 108.11 no C2 C3 H31 109.59 no C2 C3 H32 109.50 no C4 C3 H31 109.53 no C4 C3 H32 109.54 no H31 C3 H32 108.10 no C3 C4 H41 109.50 no C3 C4 H42 109.48 no C5 C4 H41 109.50 no C5 C4 H42 109.55 no H41 C4 H42 108.13 no C4 C5 H51 109.62 no C4 C5 H52 109.57 no C6 C5 H51 109.57 no C6 C5 H52 109.56 no H51 C5 H52 108.08 no N1 C6 H16 109.56 no C5 C6 H16 109.60 no C7 C6 H16 109.61 no N2 C7 H71 108.60 no C6 C7 H71 108.62 no C8 C7 H71 108.60 no C7 C8 H81 109.37 no C7 C8 H82 109.43 no C9 C8 H81 109.44 no C9 C8 H82 109.47 no H81 C8 H82 108.10 no C8 C9 H91 109.42 no C8 C9 H92 109.50 no C10 C9 H91 109.51 no C10 C9 H92 109.48 no H91 C9 H92 108.05 no C9 C10 H101 109.51 no C9 C10 H102 109.46 no C11 C10 H101 109.40 no C11 C10 H102 109.45 no H101 C10 H102 108.02 no N2 C11 H111 109.59 no N2 C11 H112 109.61 no C10 C11 H111 109.67 no C10 C11 H112 109.59 no H111 C11 H112 108.12 no Rh C12 H121 89.59 no C13 C12 H121 116.75 no C19 C12 H121 116.63 no Rh C13 H131 87.40 no C12 C13 H131 117.86 no C14 C13 H131 117.76 no C13 C14 H141 108.78 no C13 C14 H142 108.74 no C15 C14 H141 108.71 no C15 C14 H142 108.75 no H141 C14 H142 107.59 no C14 C15 H151 108.53 no C14 C15 H152 108.54 no C16 C15 H151 108.53 no C16 C15 H152 108.49 no H151 C15 H152 107.56 no Rh C16 H161 89.20 no C15 C16 H161 116.58 no C17 C16 H161 116.66 no Rh C17 H171 89.18 no C16 C17 H171 118.58 no C18 C17 H171 118.51 no C17 C18 H181 108.92 no C17 C18 H182 108.89 no C19 C18 H181 109.02 no C19 C18 H182 108.98 no H181 C18 H182 107.75 no C12 C19 H191 108.52 no C12 C19 H192 108.56 no C18 C19 H191 108.49 no C18 C19 H192 108.56 no H191 C19 H192 107.56 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Rh Cl 2.3692(7) yes Rh C1 2.0021(19) yes Rh C12 2.104(2) yes Rh C13 2.126(2) yes Rh C16 2.204(2) yes Rh C17 2.233(2) yes N1 C1 1.330(3) yes N1 C2 1.457(3) yes N1 C6 1.480(3) yes N2 C1 1.340(3) yes N2 C7 1.473(3) yes N2 C11 1.457(3) yes C2 C3 1.521(3) no C3 C4 1.528(4) no C4 C5 1.525(4) no C5 C6 1.524(3) no C6 C7 1.536(3) no C7 C8 1.525(3) no C8 C9 1.522(4) no C9 C10 1.528(4) no C10 C11 1.515(3) no C12 C13 1.403(3) no C12 C19 1.513(4) no C13 C14 1.514(4) no C14 C15 1.520(4) no C15 C16 1.507(4) no C16 C17 1.356(3) no C17 C18 1.504(3) no C18 C19 1.505(4) no C2 H21 0.9895 no C2 H22 0.9902 no C3 H31 0.9893 no C3 H32 0.9904 no C4 H41 0.9906 no C4 H42 0.9897 no C5 H51 0.9899 no C5 H52 0.9908 no C6 H16 1.0001 no C7 H71 0.9995 no C8 H81 0.9908 no C8 H82 0.9901 no C9 H91 0.9896 no C9 H92 0.9899 no C10 H101 0.9897 no C10 H102 0.9896 no C11 H111 0.9898 no C11 H112 0.9906 no C12 H121 0.9500 no C13 H131 0.9505 no C14 H141 0.9900 no C14 H142 0.9903 no C15 H151 0.9896 no C15 H152 0.9907 no C16 H161 0.9501 no C17 H171 0.9500 no C18 H181 0.9896 no C18 H182 0.9906 no C19 H191 0.9899 no C19 H192 0.9892 no _journal_paper_doi 10.1021/om060098b