#------------------------------------------------------------------------------ #$Date: 2015-02-25 15:01:53 +0200 (Wed, 25 Feb 2015) $ #$Revision: 132410 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/07/51/4075184.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_4075184 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_paper_doi 10.1021/om060098b _journal_volume 25 _journal_year 2006 _chemical_absolute_configuration ad _chemical_formula_moiety 'C20 H37 N2 O P S' _chemical_formula_sum 'C20 H37 N2 O P S' _chemical_formula_weight 384.56 _chemical_name_systematic ? _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 4 _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 110.1033(7) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.3294(1) _cell_length_b 10.0515(2) _cell_length_c 12.3944(2) _cell_measurement_reflns_used 2125 _cell_measurement_temperature 123(1) _cell_measurement_theta_max 25.33 _cell_measurement_theta_min 1.75 _cell_volume 1091.47(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 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 0.038 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 25947 _diffrn_reflns_theta_full 25.33 _diffrn_reflns_theta_max 25.33 _diffrn_reflns_theta_min 1.75 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.232 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_correction_T_min 0.886 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(applied during the scaling procedure; Nonius, 2001b)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.170 _exptl_crystal_density_meas ? _exptl_crystal_density_method none _exptl_crystal_description plate _exptl_crystal_F_000 420 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.431 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.044 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(8) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 229 _refine_ls_number_reflns 3992 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0394 _refine_ls_R_factor_gt 0.0375 _refine_ls_shift/su_max 0.000 _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^)+(0.0525P)^2^+0.5193P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_gt 0.0978 _refine_ls_wR_factor_ref 0.0991 _reflns_number_gt 3835 _reflns_number_total 3992 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file om060098bsi20060201_054503.cif _[local]_cod_data_source_block BASF-4463-123 _[local]_cod_cif_authors_sg_H-M 'P 21' _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 4075184 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,-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 S 0.0573(4) 0.0269(3) 0.0332(3) -0.0005(3) 0.0095(3) 0.0005(3) P 0.0322(3) 0.0295(3) 0.0219(3) -0.0047(2) 0.0098(2) -0.0047(3) O 0.0354(8) 0.0277(8) 0.0238(8) -0.0071(7) 0.0068(7) 0.0004(7) N1 0.0371(11) 0.0413(12) 0.0277(10) -0.0085(9) 0.0142(9) -0.0037(10) N2 0.0339(11) 0.0358(12) 0.0305(11) -0.0104(9) 0.0111(9) -0.0059(9) C1 0.0327(11) 0.0253(12) 0.0228(10) -0.0058(9) 0.0080(9) -0.0041(10) C2 0.0273(11) 0.0262(12) 0.0263(11) -0.0048(9) 0.0082(9) -0.0018(9) C3 0.0352(13) 0.0371(14) 0.0279(12) -0.0074(10) 0.0084(10) -0.0048(10) C4 0.0426(13) 0.0362(14) 0.0229(11) -0.0044(11) 0.0121(10) 0.0005(12) C5 0.0427(15) 0.0307(14) 0.0278(12) 0.0013(10) 0.0161(10) 0.0063(11) C6 0.0305(11) 0.0338(12) 0.0250(11) -0.0012(11) 0.0087(9) -0.0003(11) C7 0.0318(12) 0.0404(14) 0.0339(13) -0.0092(11) 0.0137(10) -0.0056(10) C8 0.0560(19) 0.0538(17) 0.0574(17) -0.0036(17) 0.0341(15) -0.0108(16) C9 0.0315(14) 0.071(2) 0.0508(18) -0.0091(16) 0.0141(13) 0.0048(14) C10 0.0488(17) 0.063(2) 0.0336(14) 0.0060(13) 0.0208(12) 0.0171(14) C11 0.0501(16) 0.0467(16) 0.0390(14) 0.0012(12) 0.0256(13) -0.0053(12) C12 0.0615(17) 0.0542(17) 0.0436(16) 0.0015(14) 0.0340(14) 0.0027(14) C13 0.087(2) 0.0369(15) 0.0445(16) 0.0026(13) 0.0409(16) 0.0088(15) C14 0.072(2) 0.0422(16) 0.0340(14) -0.0125(12) 0.0217(14) -0.0012(14) C15 0.0516(16) 0.0338(13) 0.0292(13) -0.0042(11) 0.0176(12) -0.0064(12) C16 0.0454(15) 0.0368(14) 0.0369(14) -0.0123(12) 0.0121(12) -0.0032(12) C17 0.0562(17) 0.0378(14) 0.0444(15) -0.0066(14) 0.0163(13) -0.0129(14) C18 0.0418(15) 0.0439(17) 0.0504(17) -0.0041(13) 0.0093(13) -0.0130(12) C19 0.0407(16) 0.069(2) 0.0493(17) -0.0041(15) 0.0189(14) -0.0148(14) C20 0.0410(15) 0.0514(18) 0.0546(17) -0.0158(14) 0.0259(13) -0.0086(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 S S Uani 0.73629(8) 0.08259(6) 0.77943(5) 1.000 0.0407(2) . . P P Uani 0.70413(7) 0.27276(6) 0.78642(5) 1.000 0.0277(2) . . O O Uani 0.58245(19) 0.32799(17) 0.66967(14) 1.000 0.0298(5) . . N1 N Uani 0.6491(2) 0.3297(2) 0.89049(17) 1.000 0.0346(6) . . N2 N Uani 0.8555(2) 0.3702(2) 0.82009(18) 1.000 0.0334(7) . . C1 C Uani 0.5311(3) 0.2563(2) 0.56071(18) 1.000 0.0273(6) . . C2 C Uani 0.3777(3) 0.3140(2) 0.48734(19) 1.000 0.0269(7) . . C3 C Uani 0.3253(3) 0.2429(3) 0.3703(2) 1.000 0.0340(8) . . C4 C Uani 0.4450(3) 0.2541(3) 0.31220(19) 1.000 0.0337(7) . . C5 C Uani 0.5979(3) 0.1978(3) 0.3864(2) 1.000 0.0327(8) . . C6 C Uani 0.6501(3) 0.2677(3) 0.50321(19) 1.000 0.0300(7) . . C7 C Uani 0.2580(3) 0.3130(3) 0.5478(2) 1.000 0.0347(8) . . C8 C Uani 0.2195(4) 0.1743(4) 0.5795(3) 1.000 0.0519(10) . . C9 C Uani 0.1138(3) 0.3882(4) 0.4768(3) 1.000 0.0511(10) . . C10 C Uani 0.7182(3) 0.2105(3) 0.3292(2) 1.000 0.0467(10) . . C11 C Uani 0.4945(3) 0.3117(3) 0.8907(2) 1.000 0.0426(9) . . C12 C Uani 0.4906(4) 0.3264(3) 1.0113(3) 1.000 0.0490(10) . . C13 C Uani 0.5649(4) 0.4548(3) 1.0657(3) 1.000 0.0514(10) . . C14 C Uani 0.7245(4) 0.4704(3) 1.0614(2) 1.000 0.0485(10) . . C15 C Uani 0.7258(3) 0.4523(3) 0.9405(2) 1.000 0.0372(8) . . C16 C Uani 0.8798(3) 0.4473(3) 0.9260(2) 1.000 0.0402(8) . . C17 C Uani 0.9543(3) 0.5779(3) 0.9197(2) 1.000 0.0464(9) . . C18 C Uani 1.0972(3) 0.5589(3) 0.8867(3) 1.000 0.0471(9) . . C19 C Uani 1.0655(4) 0.4748(4) 0.7801(3) 1.000 0.0521(10) . . C20 C Uani 0.9900(3) 0.3459(3) 0.7893(3) 1.000 0.0465(10) . . H11 H Uiso 0.51730 0.16030 0.57590 1.000 0.0330 calc R H21 H Uiso 0.39580 0.40920 0.47260 1.000 0.0320 calc R H31 H Uiso 0.30630 0.14780 0.38130 1.000 0.0410 calc R H32 H Uiso 0.22830 0.28270 0.31990 1.000 0.0410 calc R H41 H Uiso 0.40870 0.20570 0.23810 1.000 0.0400 calc R H42 H Uiso 0.45780 0.34880 0.29560 1.000 0.0400 calc R H51 H Uiso 0.58390 0.10110 0.39920 1.000 0.0390 calc R H61 H Uiso 0.74690 0.22740 0.55340 1.000 0.0360 calc R H62 H Uiso 0.66940 0.36280 0.49270 1.000 0.0360 calc R H71 H Uiso 0.30340 0.36310 0.62150 1.000 0.0420 calc R H81 H Uiso 0.31150 0.13320 0.63350 1.000 0.0780 calc R H82 H Uiso 0.18140 0.11970 0.50990 1.000 0.0780 calc R H83 H Uiso 0.14110 0.18090 0.61520 1.000 0.0780 calc R H91 H Uiso 0.14250 0.47400 0.45260 1.000 0.0770 calc R H92 H Uiso 0.04920 0.40320 0.52350 1.000 0.0770 calc R H93 H Uiso 0.05750 0.33560 0.40890 1.000 0.0770 calc R H101 H Uiso 0.81340 0.16890 0.37800 1.000 0.0700 calc R H102 H Uiso 0.73640 0.30480 0.31860 1.000 0.0700 calc R H103 H Uiso 0.68210 0.16590 0.25440 1.000 0.0700 calc R H111 H Uiso 0.45700 0.22220 0.86060 1.000 0.0510 calc R H112 H Uiso 0.42630 0.37860 0.83980 1.000 0.0510 calc R H121 H Uiso 0.38330 0.32480 1.00860 1.000 0.0590 calc R H122 H Uiso 0.54450 0.25040 1.05890 1.000 0.0590 calc R H131 H Uiso 0.56990 0.45730 1.14680 1.000 0.0620 calc R H132 H Uiso 0.50120 0.53060 1.02520 1.000 0.0620 calc R H141 H Uiso 0.76390 0.56000 1.08970 1.000 0.0580 calc R H142 H Uiso 0.79280 0.40380 1.11270 1.000 0.0580 calc R H151 H Uiso 0.66740 0.52780 0.89290 1.000 0.0450 calc R H161 H Uiso 0.95050 0.39560 0.99180 1.000 0.0480 calc R H171 H Uiso 0.98310 0.62290 0.99520 1.000 0.0560 calc R H172 H Uiso 0.88070 0.63560 0.86220 1.000 0.0560 calc R H181 H Uiso 1.13530 0.64710 0.87330 1.000 0.0560 calc R H182 H Uiso 1.17800 0.51600 0.95120 1.000 0.0560 calc R H191 H Uiso 0.99880 0.52500 0.71290 1.000 0.0630 calc R H192 H Uiso 1.16270 0.45620 0.76750 1.000 0.0630 calc R H201 H Uiso 0.96030 0.29830 0.71500 1.000 0.0560 calc R H202 H Uiso 1.06260 0.28910 0.84840 1.000 0.0560 calc R loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' 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 S P O 111.94(7) yes S P N1 118.16(8) yes S P N2 117.63(8) yes O P N1 105.81(10) yes O P N2 107.59(10) yes N1 P N2 93.77(10) yes P O C1 124.81(15) yes P N1 C11 122.32(16) yes P N1 C15 112.88(16) yes C11 N1 C15 116.6(2) yes P N2 C16 113.19(17) yes P N2 C20 125.13(18) yes C16 N2 C20 116.1(2) yes O C1 C2 107.88(18) yes O C1 C6 109.7(2) yes C2 C1 C6 112.36(19) no C1 C2 C3 108.4(2) no C1 C2 C7 113.32(19) no C3 C2 C7 114.0(2) no C2 C3 C4 111.3(2) no C3 C4 C5 112.0(2) no C4 C5 C6 109.2(2) no C4 C5 C10 112.1(2) no C6 C5 C10 110.8(2) no C1 C6 C5 111.3(2) no C2 C7 C8 113.9(2) no C2 C7 C9 110.9(2) no C8 C7 C9 111.2(3) no N1 C11 C12 110.5(2) yes C11 C12 C13 111.2(3) no C12 C13 C14 112.2(3) no C13 C14 C15 111.4(3) no N1 C15 C14 110.7(2) yes N1 C15 C16 105.7(2) yes C14 C15 C16 117.0(2) no N2 C16 C15 105.2(2) yes N2 C16 C17 110.3(2) yes C15 C16 C17 117.0(3) no C16 C17 C18 111.4(2) no C17 C18 C19 112.1(3) no C18 C19 C20 111.9(3) no N2 C20 C19 110.2(3) yes O C1 H11 108.96 no C2 C1 H11 108.95 no C6 C1 H11 108.91 no C1 C2 H21 106.91 no C3 C2 H21 106.94 no C7 C2 H21 106.91 no C2 C3 H31 109.42 no C2 C3 H32 109.42 no C4 C3 H31 109.31 no C4 C3 H32 109.31 no H31 C3 H32 107.99 no C3 C4 H41 109.19 no C3 C4 H42 109.21 no C5 C4 H41 109.25 no C5 C4 H42 109.24 no H41 C4 H42 107.87 no C4 C5 H51 108.17 no C6 C5 H51 108.20 no C10 C5 H51 108.18 no C1 C6 H61 109.33 no C1 C6 H62 109.31 no C5 C6 H61 109.36 no C5 C6 H62 109.39 no H61 C6 H62 108.06 no C2 C7 H71 106.85 no C8 C7 H71 106.75 no C9 C7 H71 106.80 no C7 C8 H81 109.44 no C7 C8 H82 109.36 no C7 C8 H83 109.48 no H81 C8 H82 109.42 no H81 C8 H83 109.58 no H82 C8 H83 109.55 no C7 C9 H91 109.39 no C7 C9 H92 109.50 no C7 C9 H93 109.46 no H91 C9 H92 109.48 no H91 C9 H93 109.52 no H92 C9 H93 109.47 no C5 C10 H101 109.46 no C5 C10 H102 109.42 no C5 C10 H103 109.46 no H101 C10 H102 109.48 no H101 C10 H103 109.44 no H102 C10 H103 109.57 no N1 C11 H111 109.53 no N1 C11 H112 109.58 no C12 C11 H111 109.58 no C12 C11 H112 109.55 no H111 C11 H112 108.10 no C11 C12 H121 109.39 no C11 C12 H122 109.46 no C13 C12 H121 109.43 no C13 C12 H122 109.40 no H121 C12 H122 107.94 no C12 C13 H131 109.22 no C12 C13 H132 109.14 no C14 C13 H131 109.20 no C14 C13 H132 109.15 no H131 C13 H132 107.80 no C13 C14 H141 109.33 no C13 C14 H142 109.30 no C15 C14 H141 109.37 no C15 C14 H142 109.40 no H141 C14 H142 107.99 no N1 C15 H151 107.67 no C14 C15 H151 107.74 no C16 C15 H151 107.64 no N2 C16 H161 108.04 no C15 C16 H161 107.95 no C17 C16 H161 108.04 no C16 C17 H171 109.32 no C16 C17 H172 109.34 no C18 C17 H171 109.29 no C18 C17 H172 109.40 no H171 C17 H172 107.98 no C17 C18 H181 109.15 no C17 C18 H182 109.22 no C19 C18 H181 109.16 no C19 C18 H182 109.19 no H181 C18 H182 107.94 no C18 C19 H191 109.18 no C18 C19 H192 109.24 no C20 C19 H191 109.21 no C20 C19 H192 109.21 no H191 C19 H192 107.99 no N2 C20 H201 109.58 no N2 C20 H202 109.62 no C19 C20 H201 109.64 no C19 C20 H202 109.58 no H201 C20 H202 108.14 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S P 1.9414(9) yes P O 1.6005(18) yes P N1 1.646(2) yes P N2 1.650(2) yes O C1 1.459(3) yes N1 C11 1.455(4) yes N1 C15 1.453(4) yes N2 C16 1.473(3) yes N2 C20 1.452(4) yes C1 C2 1.522(4) no C1 C6 1.516(4) no C2 C3 1.538(3) no C2 C7 1.544(4) no C3 C4 1.527(4) no C4 C5 1.516(4) no C5 C6 1.530(3) no C5 C10 1.525(4) no C7 C8 1.525(5) no C7 C9 1.530(4) no C11 C12 1.515(4) no C12 C13 1.510(5) no C13 C14 1.516(5) no C14 C15 1.514(4) no C15 C16 1.509(4) no C16 C17 1.500(4) no C17 C18 1.535(4) no C18 C19 1.510(5) no C19 C20 1.498(5) no C1 H11 0.9999 no C2 H21 0.9994 no C3 H31 0.9901 no C3 H32 0.9902 no C4 H41 0.9905 no C4 H42 0.9897 no C5 H51 1.0006 no C6 H61 0.9902 no C6 H62 0.9896 no C7 H71 1.0007 no C8 H81 0.9800 no C8 H82 0.9803 no C8 H83 0.9786 no C9 H91 0.9801 no C9 H92 0.9802 no C9 H93 0.9797 no C10 H101 0.9799 no C10 H102 0.9797 no C10 H103 0.9794 no C11 H111 0.9905 no C11 H112 0.9895 no C12 H121 0.9902 no C12 H122 0.9902 no C13 H131 0.9904 no C13 H132 0.9902 no C14 H141 0.9903 no C14 H142 0.9899 no C15 H151 0.9999 no C16 H161 1.0002 no C17 H171 0.9898 no C17 H172 0.9896 no C18 H181 0.9902 no C18 H182 0.9895 no C19 H191 0.9896 no C19 H192 0.9895 no C20 H201 0.9891 no C20 H202 0.9901 no