# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof. Anthony Hill' _publ_contact_author_email afhill@rsc.anu.edu.au _publ_contact_author_address ; Research School of Chemistry, The Australian National University, Canberra ACT 0200, Australia. ; _publ_contact_author_phone '+61 2 612 53640' _publ_contact_author_fax '+61 2 612 50750' _publ_section_title ; 1-Borabenzonitrile (B-cyanoboratabenzene) ; _publ_section_abstract ; The crystal structure of IAC282 is reported. ; _publ_section_comment ; The crystallographic asymmetric unit consists of one RuCp*(C5H5BCN) molecule. ; _publ_section_figure_captions ; Fig. 1. The title compound with displacement ellipsoids drawn at the 35% probability level. H atoms are shown as spheres of arbitary radius. ; # Attachment '- 13.cif' #TrackingRef '- 13.cif' _audit_creation_date 09-07-29 _audit_creation_method CRYSTALS_ver_12.85 _oxford_structure_analysis_title '7201117 iac282' _chemical_name_systematic RuCp*(C5H5B-CN) _chemical_melting_point ? loop_ _publ_author_name A.Hill I.Cade data_1 _database_code_depnum_ccdc_archive 'CCDC 749401' #TrackingRef '- 13.cif' _publ_section_exptl_refinement ; In the absence of significant anomalous scattering, Friedel pairs were merged. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep ; The compound was prepared by I.A. Cade and recrystallized from a mixture of benzene and hexane (40:60). The sample ID is IAC 282. ; _cell_length_a 7.3762(2) _cell_length_b 11.7494(3) _cell_length_c 17.3553(4) _cell_angle_alpha 90 _cell_angle_beta 92.2428(18) _cell_angle_gamma 90 _cell_volume 1502.96(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Ru -1.2594 0.8363 19.2674 0.8085 12.9182 8.4347 4.8634 24.7997 1.5676 94.2928 5.3787 'International Tables Vol C 4.2.6.8 and 6.1.1.4' B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403 -0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C16 H20 B1 N1 Ru1 # Dc = 1.49 Fooo = 688.00 Mu = 10.28 M = 338.22 # Found Formula = C16 H20 B1 N1 Ru1 # Dc = 1.49 FOOO = 688.00 Mu = 10.28 M = 338.22 _chemical_formula_sum 'C16 H20 B1 N1 Ru1' _chemical_formula_moiety 'C16 H20 B1 N1 Ru1' _chemical_compound_source ? _chemical_formula_weight 338.22 _cell_measurement_reflns_used 15955 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27 _cell_measurement_temperature 200 _exptl_crystal_description plate _exptl_crystal_colour 'pale orange' _exptl_crystal_size_min 0.03 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.22 _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 1.028 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.110 -1 0 0 0.070 -1 0 12 0.003 -1 6 10 0.034 1 -1 -10 0.025 1 -6 -11 0.020 1 -2 -4 0.010 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.871 _exptl_absorpt_correction_T_max 0.971 _exptl_absorpt_process_details ; Gaussian integration (Coppens, 1970) ; # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'Ortep-3 for Windows v. 2.01' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 24979 _reflns_number_total 3446 _diffrn_reflns_av_R_equivalents 0.066 # Number of reflections with Friedels Law is 3446 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3448 _diffrn_reflns_theta_min 3.263 _diffrn_reflns_theta_max 27.485 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.485 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _oxford_diffrn_Wilson_B_factor 2.54 _oxford_diffrn_Wilson_scale 13.72 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.85 _refine_diff_density_max 0.89 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 3444 _refine_ls_number_restraints 0 _refine_ls_number_parameters 173 _oxford_refine_ls_R_factor_ref 0.0573 _refine_ls_wR_factor_ref 0.1328 _refine_ls_goodness_of_fit_ref 0.9137 _refine_ls_shift/su_max 0.000926 # The values computed from all data _oxford_reflns_number_all 3444 _refine_ls_R_factor_all 0.0573 _refine_ls_wR_factor_all 0.1328 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2051 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_gt 0.0878 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 23.3 36.1 19.0 5.37 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Farrugia, L.J. (1997) Ortep-3 for Windows v. 2.01, J. Appl. Cryst. 30, 565. Coppens P. (1970) In Crystallographic Computing, edited by F.R. Ahmed, S.R. Hall and C.P Huber, p255-270. Copenhagen: Munksgaard ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Ru1 Ru 0.40437(3) 0.24570(2) 0.388414(14) 0.0306 1.0000 Uani . . . . . . . B2 B 0.6127(6) 0.2406(4) 0.2937(3) 0.0371 1.0000 Uani . . . . . . . C3 C 0.5535(5) 0.1218(3) 0.3165(2) 0.0389 1.0000 Uani . . . . . . . C4 C 0.5661(6) 0.0874(3) 0.3944(2) 0.0426 1.0000 Uani . . . . . . . C5 C 0.6325(5) 0.1638(4) 0.4530(2) 0.0418 1.0000 Uani . . . . . . . C6 C 0.6841(5) 0.2755(4) 0.4357(2) 0.0421 1.0000 Uani . . . . . . . C7 C 0.6760(5) 0.3162(3) 0.3588(2) 0.0392 1.0000 Uani . . . . . . . C8 C 0.5945(6) 0.2824(4) 0.2083(3) 0.0477 1.0000 Uani . . . . . . . N9 N 0.5861(7) 0.3128(5) 0.1460(2) 0.0710 1.0000 Uani . . . . . . . C10 C 0.2073(5) 0.3857(3) 0.3818(2) 0.0382 1.0000 Uani . . . . . . . C11 C 0.2123(5) 0.3386(3) 0.4582(2) 0.0359 1.0000 Uani . . . . . . . C12 C 0.1598(5) 0.2219(3) 0.4531(2) 0.0342 1.0000 Uani . . . . . . . C13 C 0.1231(5) 0.1944(4) 0.3742(2) 0.0387 1.0000 Uani . . . . . . . C14 C 0.1500(5) 0.2962(4) 0.3285(2) 0.0385 1.0000 Uani . . . . . . . C15 C 0.2391(6) 0.5067(4) 0.3606(3) 0.0519 1.0000 Uani . . . . . . . C16 C 0.2526(6) 0.4030(4) 0.5310(2) 0.0504 1.0000 Uani . . . . . . . C17 C 0.1383(6) 0.1437(4) 0.5206(3) 0.0482 1.0000 Uani . . . . . . . C18 C 0.0602(6) 0.0818(4) 0.3427(3) 0.0487 1.0000 Uani . . . . . . . C19 C 0.1156(7) 0.3084(4) 0.2440(2) 0.0542 1.0000 Uani . . . . . . . H31 H 0.4864 0.0734 0.2790 0.0468 1.0000 Uiso R . . . . . . H41 H 0.5100 0.0158 0.4098 0.0512 1.0000 Uiso R . . . . . . H51 H 0.6246 0.1417 0.5070 0.0498 1.0000 Uiso R . . . . . . H61 H 0.7035 0.3285 0.4782 0.0499 1.0000 Uiso R . . . . . . H71 H 0.6940 0.3981 0.3504 0.0467 1.0000 Uiso R . . . . . . H151 H 0.2732 0.5109 0.3077 0.0777 1.0000 Uiso R . . . . . . H152 H 0.1307 0.5507 0.3664 0.0779 1.0000 Uiso R . . . . . . H153 H 0.3357 0.5380 0.3933 0.0784 1.0000 Uiso R . . . . . . H161 H 0.3019 0.3511 0.5698 0.0758 1.0000 Uiso R . . . . . . H162 H 0.1450 0.4358 0.5494 0.0761 1.0000 Uiso R . . . . . . H163 H 0.3395 0.4613 0.5221 0.0758 1.0000 Uiso R . . . . . . H171 H 0.1456 0.0671 0.5039 0.0720 1.0000 Uiso R . . . . . . H172 H 0.0233 0.1570 0.5422 0.0719 1.0000 Uiso R . . . . . . H173 H 0.2359 0.1588 0.5583 0.0718 1.0000 Uiso R . . . . . . H181 H 0.0891 0.0763 0.2898 0.0729 1.0000 Uiso R . . . . . . H182 H -0.0682 0.0746 0.3467 0.0735 1.0000 Uiso R . . . . . . H183 H 0.1186 0.0214 0.3712 0.0729 1.0000 Uiso R . . . . . . H191 H 0.1289 0.2354 0.2199 0.0808 1.0000 Uiso R . . . . . . H192 H -0.0059 0.3356 0.2322 0.0810 1.0000 Uiso R . . . . . . H193 H 0.2013 0.3611 0.2229 0.0817 1.0000 Uiso R . . . . . . 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 Ru1 0.0283(2) 0.0340(2) 0.0297(2) 0.00086(11) 0.00198(13) 0.00137(11) B2 0.036(2) 0.043(2) 0.033(2) 0.0022(16) 0.0065(17) 0.0071(16) C3 0.037(2) 0.0405(19) 0.040(2) -0.0035(16) 0.0062(16) 0.0037(15) C4 0.040(2) 0.0386(19) 0.050(2) 0.0067(16) 0.0092(18) 0.0104(16) C5 0.0350(19) 0.056(2) 0.0347(19) 0.0056(17) -0.0013(15) 0.0146(17) C6 0.0283(18) 0.060(2) 0.037(2) -0.0095(18) -0.0037(15) -0.0007(16) C7 0.0261(17) 0.045(2) 0.047(2) 0.0007(17) 0.0021(15) -0.0030(14) C8 0.050(2) 0.052(2) 0.041(2) 0.0021(18) 0.0059(19) 0.0038(19) N9 0.086(3) 0.083(3) 0.044(2) 0.014(2) 0.009(2) 0.004(3) C10 0.0275(18) 0.0404(19) 0.047(2) 0.0062(16) 0.0066(15) 0.0050(14) C11 0.0293(17) 0.0386(18) 0.040(2) -0.0011(15) 0.0092(15) 0.0029(14) C12 0.0260(16) 0.0404(18) 0.0364(19) 0.0021(15) 0.0043(14) 0.0015(14) C13 0.0299(17) 0.040(2) 0.046(2) -0.0010(17) 0.0017(16) 0.0009(15) C14 0.0281(18) 0.049(2) 0.039(2) 0.0047(17) -0.0018(15) 0.0078(16) C15 0.051(3) 0.044(2) 0.061(3) 0.012(2) 0.016(2) 0.0075(19) C16 0.051(3) 0.051(2) 0.050(2) -0.0092(19) 0.012(2) -0.0032(19) C17 0.046(2) 0.050(2) 0.049(2) 0.0117(19) 0.0070(18) -0.0044(19) C18 0.044(2) 0.050(2) 0.053(2) -0.0106(19) -0.0016(19) -0.0098(18) C19 0.049(2) 0.070(3) 0.043(2) 0.008(2) -0.0051(19) 0.004(2) _refine_ls_extinction_coef 137(17) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.2904(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Ru1 . B2 . 2.294(4) yes Ru1 . C3 . 2.234(4) yes Ru1 . C4 . 2.210(4) yes Ru1 . C5 . 2.206(4) yes Ru1 . C6 . 2.218(4) yes Ru1 . C7 . 2.246(4) yes Ru1 . C10 . 2.195(4) yes Ru1 . C11 . 2.191(3) yes Ru1 . C12 . 2.179(4) yes Ru1 . C13 . 2.166(4) yes Ru1 . C14 . 2.191(4) yes B2 . C3 . 1.520(6) yes B2 . C7 . 1.497(6) yes B2 . C8 . 1.562(6) yes C3 . C4 . 1.411(6) yes C3 . H31 . 0.983 no C4 . C5 . 1.427(6) yes C4 . H41 . 0.979 no C5 . C6 . 1.403(6) yes C5 . H51 . 0.977 no C6 . C7 . 1.417(6) yes C6 . H61 . 0.972 no C7 . H71 . 0.983 no C8 . N9 . 1.137(6) yes C10 . C11 . 1.435(5) yes C10 . C14 . 1.453(6) yes C10 . C15 . 1.489(5) yes C11 . C12 . 1.427(5) yes C11 . C16 . 1.493(5) yes C12 . C13 . 1.422(6) yes C12 . C17 . 1.503(5) yes C13 . C14 . 1.453(6) yes C13 . C18 . 1.497(6) yes C14 . C19 . 1.485(6) yes C15 . H151 . 0.963 no C15 . H152 . 0.960 no C15 . H153 . 0.965 no C16 . H161 . 0.968 no C16 . H162 . 0.949 no C16 . H163 . 0.955 no C17 . H171 . 0.948 no C17 . H172 . 0.954 no C17 . H173 . 0.970 no C18 . H181 . 0.952 no C18 . H182 . 0.956 no C18 . H183 . 0.958 no C19 . H191 . 0.961 no C19 . H192 . 0.966 no C19 . H193 . 0.967 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag B2 . Ru1 . C3 . 39.19(14) yes B2 . Ru1 . C4 . 68.69(15) yes C3 . Ru1 . C4 . 37.01(15) yes B2 . Ru1 . C5 . 80.42(16) yes C3 . Ru1 . C5 . 67.46(15) yes C4 . Ru1 . C5 . 37.71(16) yes B2 . Ru1 . C6 . 68.27(17) yes C3 . Ru1 . C6 . 80.68(16) yes C4 . Ru1 . C6 . 67.83(17) yes C5 . Ru1 . C6 . 36.97(16) yes B2 . Ru1 . C7 . 38.49(16) yes C3 . Ru1 . C7 . 69.48(15) yes C4 . Ru1 . C7 . 80.59(15) yes C5 . Ru1 . C7 . 66.90(15) yes C6 . Ru1 . C7 . 36.99(15) yes B2 . Ru1 . C10 . 116.29(15) yes C3 . Ru1 . C10 . 143.00(15) yes C4 . Ru1 . C10 . 171.22(16) yes C5 . Ru1 . C10 . 147.56(16) yes C6 . Ru1 . C10 . 120.37(16) yes B2 . Ru1 . C11 . 151.02(14) yes C3 . Ru1 . C11 . 167.52(15) yes C4 . Ru1 . C11 . 138.83(14) yes C5 . Ru1 . C11 . 115.70(15) yes C6 . Ru1 . C11 . 109.23(15) yes B2 . Ru1 . C12 . 163.03(18) yes C3 . Ru1 . C12 . 129.74(15) yes C4 . Ru1 . C12 . 108.90(15) yes C5 . Ru1 . C12 . 108.24(15) yes C6 . Ru1 . C12 . 127.35(15) yes B2 . Ru1 . C13 . 125.19(17) yes C3 . Ru1 . C13 . 104.20(15) yes C4 . Ru1 . C13 . 106.51(16) yes C5 . Ru1 . C13 . 130.16(16) yes C6 . Ru1 . C13 . 163.62(17) yes B2 . Ru1 . C14 . 104.59(16) yes C3 . Ru1 . C14 . 110.03(15) yes C4 . Ru1 . C14 . 134.52(17) yes C5 . Ru1 . C14 . 168.89(17) yes C6 . Ru1 . C14 . 154.10(19) yes C7 . Ru1 . C10 . 107.85(14) yes C7 . Ru1 . C11 . 123.01(14) yes C10 . Ru1 . C11 . 38.21(14) yes C7 . Ru1 . C12 . 158.27(16) yes C10 . Ru1 . C12 . 64.10(14) yes C11 . Ru1 . C12 . 38.11(13) yes C7 . Ru1 . C13 . 159.35(16) yes C10 . Ru1 . C13 . 64.73(14) yes C11 . Ru1 . C13 . 64.18(15) yes C12 . Ru1 . C13 . 38.22(15) yes C7 . Ru1 . C14 . 123.11(15) yes C10 . Ru1 . C14 . 38.68(15) yes C11 . Ru1 . C14 . 64.36(15) yes C12 . Ru1 . C14 . 64.44(14) yes C13 . Ru1 . C14 . 38.97(16) yes Ru1 . B2 . C3 . 68.3(2) yes Ru1 . B2 . C7 . 69.0(2) yes C3 . B2 . C7 . 115.6(4) yes Ru1 . B2 . C8 . 129.6(3) yes C3 . B2 . C8 . 121.5(4) yes C7 . B2 . C8 . 122.8(4) yes Ru1 . C3 . B2 . 72.5(2) yes Ru1 . C3 . C4 . 70.6(2) yes B2 . C3 . C4 . 120.3(4) yes Ru1 . C3 . H31 . 120.0 no B2 . C3 . H31 . 120.0 no C4 . C3 . H31 . 118.8 no Ru1 . C4 . C3 . 72.4(2) yes Ru1 . C4 . C5 . 71.0(2) yes C3 . C4 . C5 . 120.7(4) yes Ru1 . C4 . H41 . 120.2 no C3 . C4 . H41 . 119.6 no C5 . C4 . H41 . 118.9 no Ru1 . C5 . C4 . 71.3(2) yes Ru1 . C5 . C6 . 72.0(2) yes C4 . C5 . C6 . 121.6(4) yes Ru1 . C5 . H51 . 122.0 no C4 . C5 . H51 . 119.0 no C6 . C5 . H51 . 118.7 no Ru1 . C6 . C5 . 71.0(2) yes Ru1 . C6 . C7 . 72.6(2) yes C5 . C6 . C7 . 121.0(4) yes Ru1 . C6 . H61 . 119.3 no C5 . C6 . H61 . 118.0 no C7 . C6 . H61 . 119.9 no Ru1 . C7 . C6 . 70.4(2) yes Ru1 . C7 . B2 . 72.5(2) yes C6 . C7 . B2 . 120.7(4) yes Ru1 . C7 . H71 . 121.4 no C6 . C7 . H71 . 117.9 no B2 . C7 . H71 . 120.6 no B2 . C8 . N9 . 178.2(5) yes Ru1 . C10 . C11 . 70.7(2) yes Ru1 . C10 . C14 . 70.5(2) yes C11 . C10 . C14 . 107.8(3) yes Ru1 . C10 . C15 . 128.2(3) yes C11 . C10 . C15 . 126.7(4) yes C14 . C10 . C15 . 125.3(4) yes Ru1 . C11 . C10 . 71.1(2) yes Ru1 . C11 . C12 . 70.51(19) yes C10 . C11 . C12 . 108.4(3) yes Ru1 . C11 . C16 . 127.5(3) yes C10 . C11 . C16 . 125.7(4) yes C12 . C11 . C16 . 125.8(3) yes Ru1 . C12 . C11 . 71.39(19) yes Ru1 . C12 . C13 . 70.4(2) yes C11 . C12 . C13 . 108.7(3) yes Ru1 . C12 . C17 . 126.5(3) yes C11 . C12 . C17 . 125.1(4) yes C13 . C12 . C17 . 126.1(4) yes Ru1 . C13 . C12 . 71.4(2) yes Ru1 . C13 . C14 . 71.5(2) yes C12 . C13 . C14 . 108.2(4) yes Ru1 . C13 . C18 . 124.7(3) yes C12 . C13 . C18 . 126.6(4) yes C14 . C13 . C18 . 125.1(4) yes Ru1 . C14 . C13 . 69.6(2) yes Ru1 . C14 . C10 . 70.8(2) yes C13 . C14 . C10 . 106.9(4) yes Ru1 . C14 . C19 . 127.2(3) yes C13 . C14 . C19 . 126.6(4) yes C10 . C14 . C19 . 126.4(4) yes C10 . C15 . H151 . 109.6 no C10 . C15 . H152 . 110.4 no H151 . C15 . H152 . 108.7 no C10 . C15 . H153 . 109.8 no H151 . C15 . H153 . 109.0 no H152 . C15 . H153 . 109.4 no C11 . C16 . H161 . 109.1 no C11 . C16 . H162 . 110.4 no H161 . C16 . H162 . 108.6 no C11 . C16 . H163 . 109.8 no H161 . C16 . H163 . 109.2 no H162 . C16 . H163 . 109.8 no C12 . C17 . H171 . 109.5 no C12 . C17 . H172 . 109.2 no H171 . C17 . H172 . 109.8 no C12 . C17 . H173 . 108.4 no H171 . C17 . H173 . 109.3 no H172 . C17 . H173 . 110.6 no C13 . C18 . H181 . 109.5 no C13 . C18 . H182 . 110.2 no H181 . C18 . H182 . 109.0 no C13 . C18 . H183 . 109.9 no H181 . C18 . H183 . 109.5 no H182 . C18 . H183 . 108.8 no C14 . C19 . H191 . 109.1 no C14 . C19 . H192 . 111.2 no H191 . C19 . H192 . 108.2 no C14 . C19 . H193 . 110.3 no H191 . C19 . H193 . 109.1 no H192 . C19 . H193 . 108.9 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C5 . H51 . N9 4_555 152 0.98 2.50 3.393(6) yes # Attachment '- [Bu4N][3].cif' _audit_creation_date 09-05-06 _audit_creation_method CRYSTALS_ver_12.85 _oxford_structure_analysis_title '5061858 iac193' _chemical_name_systematic ? _chemical_melting_point ? _chemical_name_common RuCp*(C5H5B-CN) data_2 _database_code_depnum_ccdc_archive 'CCDC 823550' #TrackingRef '- [Bu4N][3].cif' _publ_section_exptl_refinement ; Due to the diffuse nature of the outer reflections, the data, though collected to 25 degrees, was manually restricted to 23.245 degrees this has resulted in a low theta max (less than 25 degrees) and low sin(theta_max)/wavelength. The poor Data/Parameter ratio is a result of the title compound crystallising in a non-centrosymmetric spacegroup without the presence of heavy atoms, which would otherwise allow a Flack parameter to be refined. Additionally, this poor Data/Parameter ratio is also a result of the absence of good data to high theta. (see previous comment) The absence of elements of high atomic mass and the presence of a molecule of benzene (density 0.874 gcm-3) in the structure is consistent with a rather low calculated density of 0.98 gcm-3 In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. The refinement was carried out with the cyanide moiety set as either carbon- or nitrogen-bound to the borabenzene moiety in order to determine which of these two possible linkage isomers were present. The carbon-bound cyanide gave the best refinement. ; _cell_length_a 9.6193(4) _cell_length_b 9.6193(4) _cell_length_c 30.8153(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2851.37(19) _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M 'P 41 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -y,x,z+1/4 -x,-y,z+1/2 y,-x,z+3/4 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403 -0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C22 H41 B1 N2 # Dc = 0.80 Fooo = 936.00 Mu = 0.46 M = 344.39 # Found Formula = C28 H47 B1 N2 # Dc = 0.98 FOOO = 936.00 Mu = 0.56 M = 422.51 _chemical_formula_sum 'C28 H47 B1 N2' _chemical_formula_moiety 'C16 H36 N, 0.5(C12 H12), C6 H5 B N' _chemical_compound_source 'Research School of Chemistry' _chemical_formula_weight 422.51 _cell_measurement_reflns_used 14360 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 23.26 _cell_measurement_temperature 200 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.23 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_max 0.87 _exptl_crystal_density_diffrn 0.984 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.056 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.69 _exptl_absorpt_correction_T_max 0.99 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'Ortep-3 for Windows v. 2.01' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 9043 _reflns_number_total 2087 _diffrn_reflns_av_R_equivalents 0.049 # Number of reflections with Friedels Law is 2087 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2045 _diffrn_reflns_theta_min 2.644 _diffrn_reflns_theta_max 23.245 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 23.245 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 32 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 33 _oxford_diffrn_Wilson_B_factor 4.50 _oxford_diffrn_Wilson_scale 10.93 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.29 _refine_diff_density_max 0.31 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 2087 _refine_ls_number_restraints 85 _refine_ls_number_parameters 334 _oxford_refine_ls_R_factor_ref 0.0938 _refine_ls_wR_factor_ref 0.1018 _refine_ls_goodness_of_fit_ref 0.8728 _refine_ls_shift/su_max 0.018014 # The values computed from all data _oxford_reflns_number_all 2087 _refine_ls_R_factor_all 0.0938 _refine_ls_wR_factor_all 0.1018 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1157 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_gt 0.0892 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.00P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Farrugia, L.J. (1997) Ortep-3 for Windows v. 2.01, J. Appl. Cryst. 30, 565. Coppens P. (1970) In Crystallographic Computing, edited by F.R. Ahmed, S.R. Hall and C.P Huber, p255-270. Copenhagen: Munksgaard ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens B1 B 0.2669(6) 0.2399(7) 0.65018(14) 0.0686 1.0000 Uani . . . . . . . C2 C 0.1805(6) 0.3569(5) 0.63455(13) 0.0763 1.0000 Uani . . . . . . . C3 C 0.0418(7) 0.3301(7) 0.62321(15) 0.0926 1.0000 Uani . . . . . . . C4 C -0.0139(7) 0.1960(9) 0.62693(16) 0.0988 1.0000 Uani . . . . . . . C5 C 0.0631(7) 0.0860(6) 0.64115(16) 0.0918 1.0000 Uani . . . . . . . C6 C 0.2009(6) 0.1005(6) 0.65298(15) 0.0834 1.0000 Uani . . . . . . . C7 C 0.4237(7) 0.2579(5) 0.66106(15) 0.0737 1.0000 Uani . . . . . . . N8 N 0.5406(5) 0.2688(4) 0.66840(15) 0.0993 1.0000 Uani . . . . . . . N9 N 0.3419(3) 0.0991(3) 0.51200(12) 0.0408 1.0000 Uani . . . . . . . C10 C 0.3999(4) 0.2166(4) 0.54000(12) 0.0458 1.0000 Uani . . . . . . . C11 C 0.4524(4) 0.3416(4) 0.51525(12) 0.0506 1.0000 Uani . . . . . . . C12 C 0.5016(5) 0.4527(4) 0.54662(14) 0.0601 1.0000 Uani . . . . . . . C13 C 0.5514(5) 0.5829(4) 0.52372(14) 0.0712 1.0000 Uani . . . . . . . C14 C 0.2215(4) 0.1499(4) 0.48437(12) 0.0443 1.0000 Uani . . . . . . . C15 C 0.0995(4) 0.2099(4) 0.50965(12) 0.0537 1.0000 Uani . . . . . . . C16 C -0.0127(4) 0.2570(4) 0.47853(14) 0.0612 1.0000 Uani . . . . . . . C17 C -0.1389(4) 0.3152(5) 0.50162(15) 0.0803 1.0000 Uani . . . . . . . C18 C 0.2942(4) -0.0135(4) 0.54322(12) 0.0435 1.0000 Uani . . . . . . . C19 C 0.2253(4) -0.1390(4) 0.52214(12) 0.0505 1.0000 Uani . . . . . . . C20 C 0.1877(4) -0.2472(4) 0.55551(13) 0.0619 1.0000 Uani . . . . . . . C21 C 0.1170(5) -0.3735(4) 0.53593(16) 0.0768 1.0000 Uani . . . . . . . C22 C 0.4511(4) 0.0437(4) 0.48087(12) 0.0466 1.0000 Uani . . . . . . . C23 C 0.5816(4) -0.0121(4) 0.50179(12) 0.0545 1.0000 Uani . . . . . . . C24 C 0.6855(4) -0.0624(5) 0.46847(15) 0.0783 1.0000 Uani . . . . . . . C25 C 0.8145(5) -0.1217(5) 0.48906(18) 0.0921 1.0000 Uani . . . . . . . C290 C 0.6821(17) 0.232(2) 0.3738(9) 0.0864 0.5000 Uani D U . . . . . C291 C 0.7334(17) 0.235(2) 0.3698(8) 0.0912 0.5000 Uani D U . . . . . C280 C 0.601(3) 0.340(2) 0.3888(11) 0.0867 0.5000 Uani D U . . . . . C281 C 0.619(3) 0.302(2) 0.3861(10) 0.0907 0.5000 Uani D U . . . . . C270 C 0.661(2) 0.468(2) 0.3974(10) 0.0841 0.5000 Uani D U . . . . . C271 C 0.6271(19) 0.439(2) 0.4003(9) 0.0825 0.5000 Uani D U . . . . . C260 C 0.805(2) 0.4806(18) 0.3916(7) 0.0824 0.5000 Uani D U . . . . . C261 C 0.7543(12) 0.5107(17) 0.3975(6) 0.0760 0.5000 Uani D U . . . . . C310 C 0.8870(17) 0.3765(17) 0.3741(6) 0.0818 0.5000 Uani D U . . . . . C311 C 0.8730(13) 0.4411(13) 0.3830(5) 0.0694 0.5000 Uani D U . . . . . C300 C 0.8232(17) 0.2485(17) 0.3662(7) 0.0822 0.5000 Uani D U . . . . . C301 C 0.8607(16) 0.3037(14) 0.3689(5) 0.0776 0.5000 Uani D U . . . . . H21 H 0.2197 0.4528 0.6321 0.0899 1.0000 Uiso R . . . . . . H31 H -0.0182 0.4075 0.6124 0.1097 1.0000 Uiso R . . . . . . H41 H -0.1132 0.1805 0.6186 0.1158 1.0000 Uiso R . . . . . . H51 H 0.0181 -0.0074 0.6435 0.1068 1.0000 Uiso R . . . . . . H61 H 0.2558 0.0181 0.6629 0.0996 1.0000 Uiso R . . . . . . H101 H 0.4787 0.1786 0.5575 0.0530 1.0000 Uiso R . . . . . . H102 H 0.3243 0.2488 0.5599 0.0530 1.0000 Uiso R . . . . . . H111 H 0.5318 0.3127 0.4963 0.0601 1.0000 Uiso R . . . . . . H112 H 0.3758 0.3796 0.4968 0.0601 1.0000 Uiso R . . . . . . H121 H 0.5794 0.4141 0.5645 0.0690 1.0000 Uiso R . . . . . . H122 H 0.4223 0.4782 0.5660 0.0690 1.0000 Uiso R . . . . . . H131 H 0.5822 0.6528 0.5458 0.0840 1.0000 Uiso R . . . . . . H132 H 0.6313 0.5588 0.5044 0.0840 1.0000 Uiso R . . . . . . H133 H 0.4742 0.6230 0.5059 0.0840 1.0000 Uiso R . . . . . . H141 H 0.2574 0.2241 0.4646 0.0507 1.0000 Uiso R . . . . . . H142 H 0.1865 0.0700 0.4667 0.0507 1.0000 Uiso R . . . . . . H151 H 0.1320 0.2909 0.5273 0.0631 1.0000 Uiso R . . . . . . H152 H 0.0611 0.1368 0.5294 0.0631 1.0000 Uiso R . . . . . . H161 H 0.0264 0.3310 0.4593 0.0723 1.0000 Uiso R . . . . . . H162 H -0.0423 0.1758 0.4605 0.0723 1.0000 Uiso R . . . . . . H171 H -0.2101 0.3450 0.4799 0.0956 1.0000 Uiso R . . . . . . H172 H -0.1105 0.3969 0.5196 0.0956 1.0000 Uiso R . . . . . . H173 H -0.1793 0.2417 0.5208 0.0956 1.0000 Uiso R . . . . . . H181 H 0.3772 -0.0469 0.5597 0.0511 1.0000 Uiso R . . . . . . H182 H 0.2260 0.0291 0.5638 0.0511 1.0000 Uiso R . . . . . . H191 H 0.2908 -0.1807 0.5006 0.0592 1.0000 Uiso R . . . . . . H192 H 0.1387 -0.1081 0.5070 0.0592 1.0000 Uiso R . . . . . . H201 H 0.2748 -0.2781 0.5704 0.0721 1.0000 Uiso R . . . . . . H202 H 0.1235 -0.2043 0.5772 0.0721 1.0000 Uiso R . . . . . . H211 H 0.0948 -0.4415 0.5595 0.0883 1.0000 Uiso R . . . . . . H212 H 0.1804 -0.4181 0.5143 0.0883 1.0000 Uiso R . . . . . . H213 H 0.0291 -0.3443 0.5212 0.0883 1.0000 Uiso R . . . . . . H221 H 0.4782 0.1211 0.4609 0.0543 1.0000 Uiso R . . . . . . H222 H 0.4082 -0.0333 0.4637 0.0543 1.0000 Uiso R . . . . . . H231 H 0.6254 0.0638 0.5192 0.0652 1.0000 Uiso R . . . . . . H232 H 0.5563 -0.0911 0.5213 0.0652 1.0000 Uiso R . . . . . . H241 H 0.7128 0.0175 0.4495 0.0929 1.0000 Uiso R . . . . . . H242 H 0.6403 -0.1360 0.4504 0.0929 1.0000 Uiso R . . . . . . H251 H 0.8797 -0.1538 0.4659 0.1107 1.0000 Uiso R . . . . . . H252 H 0.8610 -0.0487 0.5071 0.1107 1.0000 Uiso R . . . . . . H253 H 0.7884 -0.2022 0.5079 0.1107 1.0000 Uiso R . . . . . . H2601 H 0.8452 0.5757 0.3952 0.1049 0.5000 Uiso R . . . . . . H2701 H 0.5993 0.5428 0.4094 0.0991 0.5000 Uiso R . . . . . . H2801 H 0.4999 0.3228 0.3944 0.0998 0.5000 Uiso R . . . . . . H2901 H 0.6375 0.1398 0.3688 0.1023 0.5000 Uiso R . . . . . . H3001 H 0.8838 0.1754 0.3530 0.0950 0.5000 Uiso R . . . . . . H3101 H 0.9895 0.3932 0.3726 0.0959 0.5000 Uiso R . . . . . . H2611 H 0.7575 0.6047 0.4113 0.1053 0.5000 Uiso R . . . . . . H2711 H 0.5429 0.4904 0.4103 0.0970 0.5000 Uiso R . . . . . . H2811 H 0.5267 0.2538 0.3862 0.1014 0.5000 Uiso R . . . . . . H2911 H 0.7287 0.1366 0.3597 0.1071 0.5000 Uiso R . . . . . . H3011 H 0.9444 0.2528 0.3580 0.0886 0.5000 Uiso R . . . . . . H3111 H 0.9617 0.4949 0.3814 0.0900 0.5000 Uiso R . . . . . . 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 B1 0.081(4) 0.089(5) 0.036(3) -0.007(3) 0.012(3) 0.002(4) C2 0.084(4) 0.095(4) 0.051(3) -0.002(3) 0.017(3) 0.006(3) C3 0.105(5) 0.120(5) 0.054(3) 0.010(3) 0.015(3) 0.027(4) C4 0.087(5) 0.154(6) 0.055(3) -0.011(4) 0.022(3) -0.010(5) C5 0.115(6) 0.098(5) 0.062(3) -0.014(3) 0.031(4) -0.021(4) C6 0.096(5) 0.097(4) 0.058(3) -0.008(3) 0.026(3) -0.010(3) C7 0.105(5) 0.068(3) 0.049(3) 0.002(2) -0.006(3) -0.003(3) N8 0.114(4) 0.095(3) 0.089(3) 0.004(2) -0.029(3) -0.001(3) N9 0.048(2) 0.041(2) 0.0335(14) -0.0027(15) -0.0005(15) -0.003(2) C10 0.052(3) 0.046(3) 0.039(2) -0.008(2) -0.0034(19) 0.001(2) C11 0.050(3) 0.047(3) 0.054(2) -0.001(2) -0.002(2) -0.002(2) C12 0.071(3) 0.047(3) 0.063(2) -0.007(2) -0.005(2) -0.007(2) C13 0.078(4) 0.052(3) 0.083(3) -0.004(3) -0.001(3) -0.012(2) C14 0.048(3) 0.051(3) 0.0343(19) 0.0028(19) -0.006(2) -0.001(2) C15 0.050(3) 0.055(3) 0.056(2) -0.001(2) -0.002(2) 0.005(2) C16 0.046(3) 0.072(3) 0.066(2) 0.015(2) -0.011(2) 0.005(2) C17 0.052(3) 0.088(4) 0.101(4) 0.009(3) -0.017(3) 0.009(3) C18 0.044(2) 0.045(3) 0.041(2) 0.007(2) -0.0005(19) 0.002(2) C19 0.056(3) 0.042(2) 0.053(2) 0.004(2) -0.002(2) -0.003(2) C20 0.063(3) 0.056(3) 0.068(3) 0.007(2) 0.000(2) -0.007(2) C21 0.080(4) 0.055(3) 0.095(4) 0.010(3) -0.002(3) -0.014(3) C22 0.055(3) 0.045(3) 0.041(2) -0.0075(19) 0.012(2) 0.001(2) C23 0.050(3) 0.052(3) 0.061(3) 0.002(2) 0.008(2) 0.007(2) C24 0.059(3) 0.088(4) 0.088(3) 0.000(3) 0.019(3) 0.016(3) C25 0.068(4) 0.088(4) 0.120(4) 0.008(3) 0.033(3) 0.018(3) C290 0.080(8) 0.095(6) 0.084(6) 0.022(5) -0.005(7) 0.008(7) C291 0.089(11) 0.097(6) 0.087(7) 0.023(6) -0.002(11) 0.003(10) C280 0.091(6) 0.099(8) 0.071(5) 0.023(6) -0.011(5) 0.002(6) C281 0.098(8) 0.105(10) 0.069(7) 0.023(9) -0.021(7) -0.004(8) C270 0.086(7) 0.102(7) 0.064(5) 0.024(6) -0.007(6) -0.001(6) C271 0.085(8) 0.105(10) 0.057(6) 0.022(8) 0.003(7) -0.008(7) C260 0.072(8) 0.099(7) 0.076(5) 0.027(5) -0.008(7) -0.002(6) C261 0.046(9) 0.108(8) 0.074(7) 0.022(6) -0.010(7) 0.011(7) C310 0.070(6) 0.095(8) 0.080(6) 0.028(7) -0.002(5) 0.012(7) C311 0.055(6) 0.078(9) 0.075(7) 0.022(7) 0.008(6) 0.031(7) C300 0.073(7) 0.093(8) 0.081(5) 0.031(7) -0.004(6) 0.010(7) C301 0.082(9) 0.073(10) 0.078(6) 0.028(9) 0.004(7) -0.006(8) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3092(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag B1 . C2 . 1.479(6) yes B1 . C6 . 1.487(7) yes B1 . C7 . 1.555(8) yes C2 . C3 . 1.403(7) yes C2 . H21 . 1.000 no C3 . C4 . 1.401(7) yes C3 . H31 . 1.000 no C4 . C5 . 1.364(7) yes C4 . H41 . 1.000 no C5 . C6 . 1.381(6) yes C5 . H51 . 1.000 no C6 . H61 . 1.000 no C7 . N8 . 1.152(5) yes N9 . C10 . 1.528(4) yes N9 . C14 . 1.518(4) yes N9 . C18 . 1.519(4) yes N9 . C22 . 1.519(4) yes C10 . C11 . 1.511(5) yes C10 . H101 . 1.000 no C10 . H102 . 1.000 no C11 . C12 . 1.517(5) yes C11 . H111 . 1.000 no C11 . H112 . 1.000 no C12 . C13 . 1.516(5) yes C12 . H121 . 1.000 no C12 . H122 . 1.000 no C13 . H131 . 1.000 no C13 . H132 . 1.000 no C13 . H133 . 1.000 no C14 . C15 . 1.522(5) yes C14 . H141 . 1.000 no C14 . H142 . 1.000 no C15 . C16 . 1.513(5) yes C15 . H151 . 1.000 no C15 . H152 . 1.000 no C16 . C17 . 1.515(5) yes C16 . H161 . 1.000 no C16 . H162 . 1.000 no C17 . H171 . 1.000 no C17 . H172 . 1.000 no C17 . H173 . 1.000 no C18 . C19 . 1.523(5) yes C18 . H181 . 1.000 no C18 . H182 . 1.000 no C19 . C20 . 1.507(5) yes C19 . H191 . 1.000 no C19 . H192 . 1.000 no C20 . C21 . 1.517(5) yes C20 . H201 . 1.000 no C20 . H202 . 1.000 no C21 . H211 . 1.000 no C21 . H212 . 1.000 no C21 . H213 . 1.000 no C22 . C23 . 1.509(4) yes C22 . H221 . 1.000 no C22 . H222 . 1.000 no C23 . C24 . 1.513(5) yes C23 . H231 . 1.000 no C23 . H232 . 1.000 no C24 . C25 . 1.506(6) yes C24 . H241 . 1.000 no C24 . H242 . 1.000 no C25 . H251 . 1.000 no C25 . H252 . 1.000 no C25 . H253 . 1.000 no C290 . C280 . 1.376(9) yes C290 . C300 . 1.386(9) yes C290 . H2901 . 1.000 no C291 . C281 . 1.371(9) yes C291 . C301 . 1.390(9) yes C291 . H2911 . 1.000 no C280 . C270 . 1.388(9) yes C280 . H2801 . 1.000 no C281 . C271 . 1.386(9) yes C281 . H2811 . 1.000 no C270 . C260 . 1.403(9) yes C270 . H2701 . 1.000 no C271 . C261 . 1.409(9) yes C271 . H2711 . 1.000 no C260 . C310 . 1.386(9) yes C260 . H2601 . 1.000 no C261 . C311 . 1.397(8) yes C261 . H2611 . 1.000 no C310 . C300 . 1.397(9) yes C310 . H3101 . 1.000 no C311 . C301 . 1.397(9) yes C311 . H3111 . 1.000 no C300 . H3001 . 1.000 no C301 . H3011 . 1.000 no H2701 . H2711 . 0.740 no H2801 . H2811 . 0.756 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . B1 . C6 . 117.7(5) yes C2 . B1 . C7 . 122.1(5) yes C6 . B1 . C7 . 120.2(5) yes B1 . C2 . C3 . 118.4(5) yes B1 . C2 . H21 . 121.0 no C3 . C2 . H21 . 120.6 no C2 . C3 . C4 . 120.9(5) yes C2 . C3 . H31 . 119.7 no C4 . C3 . H31 . 119.5 no C3 . C4 . C5 . 122.1(6) yes C3 . C4 . H41 . 118.8 no C5 . C4 . H41 . 119.1 no C4 . C5 . C6 . 121.9(6) yes C4 . C5 . H51 . 119.0 no C6 . C5 . H51 . 119.1 no C5 . C6 . B1 . 119.0(5) yes C5 . C6 . H61 . 120.5 no B1 . C6 . H61 . 120.4 no B1 . C7 . N8 . 178.3(5) yes C10 . N9 . C14 . 110.9(3) yes C10 . N9 . C18 . 106.3(3) yes C14 . N9 . C18 . 110.8(3) yes C10 . N9 . C22 . 111.3(3) yes C14 . N9 . C22 . 106.6(3) yes C18 . N9 . C22 . 111.0(3) yes N9 . C10 . C11 . 115.2(3) yes N9 . C10 . H101 . 108.1 no C11 . C10 . H101 . 108.0 no N9 . C10 . H102 . 108.1 no C11 . C10 . H102 . 107.9 no H101 . C10 . H102 . 109.5 no C10 . C11 . C12 . 110.1(3) yes C10 . C11 . H111 . 109.2 no C12 . C11 . H111 . 109.2 no C10 . C11 . H112 . 109.3 no C12 . C11 . H112 . 109.5 no H111 . C11 . H112 . 109.5 no C11 . C12 . C13 . 112.6(3) yes C11 . C12 . H121 . 108.8 no C13 . C12 . H121 . 109.1 no C11 . C12 . H122 . 108.4 no C13 . C12 . H122 . 108.4 no H121 . C12 . H122 . 109.5 no C12 . C13 . H131 . 109.4 no C12 . C13 . H132 . 109.2 no H131 . C13 . H132 . 109.5 no C12 . C13 . H133 . 109.8 no H131 . C13 . H133 . 109.5 no H132 . C13 . H133 . 109.5 no N9 . C14 . C15 . 115.0(3) yes N9 . C14 . H141 . 108.0 no C15 . C14 . H141 . 107.9 no N9 . C14 . H142 . 108.3 no C15 . C14 . H142 . 108.1 no H141 . C14 . H142 . 109.5 no C14 . C15 . C16 . 109.8(3) yes C14 . C15 . H151 . 109.4 no C16 . C15 . H151 . 109.5 no C14 . C15 . H152 . 109.3 no C16 . C15 . H152 . 109.4 no H151 . C15 . H152 . 109.5 no C15 . C16 . C17 . 112.6(3) yes C15 . C16 . H161 . 108.7 no C17 . C16 . H161 . 108.5 no C15 . C16 . H162 . 108.8 no C17 . C16 . H162 . 108.7 no H161 . C16 . H162 . 109.5 no C16 . C17 . H171 . 109.9 no C16 . C17 . H172 . 109.4 no H171 . C17 . H172 . 109.5 no C16 . C17 . H173 . 109.1 no H171 . C17 . H173 . 109.5 no H172 . C17 . H173 . 109.5 no N9 . C18 . C19 . 115.2(3) yes N9 . C18 . H181 . 108.1 no C19 . C18 . H181 . 108.0 no N9 . C18 . H182 . 107.9 no C19 . C18 . H182 . 108.1 no H181 . C18 . H182 . 109.5 no C18 . C19 . C20 . 111.2(3) yes C18 . C19 . H191 . 109.1 no C20 . C19 . H191 . 109.1 no C18 . C19 . H192 . 109.1 no C20 . C19 . H192 . 108.9 no H191 . C19 . H192 . 109.5 no C19 . C20 . C21 . 112.9(3) yes C19 . C20 . H201 . 108.4 no C21 . C20 . H201 . 108.7 no C19 . C20 . H202 . 108.6 no C21 . C20 . H202 . 108.7 no H201 . C20 . H202 . 109.5 no C20 . C21 . H211 . 109.3 no C20 . C21 . H212 . 109.6 no H211 . C21 . H212 . 109.5 no C20 . C21 . H213 . 109.6 no H211 . C21 . H213 . 109.5 no H212 . C21 . H213 . 109.5 no N9 . C22 . C23 . 115.5(3) yes N9 . C22 . H221 . 107.9 no C23 . C22 . H221 . 108.1 no N9 . C22 . H222 . 108.0 no C23 . C22 . H222 . 107.8 no H221 . C22 . H222 . 109.5 no C22 . C23 . C24 . 111.9(3) yes C22 . C23 . H231 . 108.7 no C24 . C23 . H231 . 108.6 no C22 . C23 . H232 . 109.0 no C24 . C23 . H232 . 109.0 no H231 . C23 . H232 . 109.5 no C23 . C24 . C25 . 112.3(4) yes C23 . C24 . H241 . 108.9 no C25 . C24 . H241 . 108.7 no C23 . C24 . H242 . 108.5 no C25 . C24 . H242 . 109.0 no H241 . C24 . H242 . 109.5 no C24 . C25 . H251 . 109.5 no C24 . C25 . H252 . 109.6 no H251 . C25 . H252 . 109.5 no C24 . C25 . H253 . 109.3 no H251 . C25 . H253 . 109.5 no H252 . C25 . H253 . 109.5 no C280 . C290 . C300 . 122(2) yes C280 . C290 . C301 . 105.9(19) yes C300 . C290 . C301 . 15.9(10) yes C280 . C290 . H2901 . 118.5 no C300 . C290 . H2901 . 119.6 no C281 . C291 . C301 . 120(2) yes C281 . C291 . H2901 . 76.7 no C301 . C291 . H2901 . 163.2 no C281 . C291 . H2911 . 121.5 no C301 . C291 . H2911 . 118.9 no C290 . C280 . C270 . 120(3) yes C290 . C280 . H2801 . 119.1 no C270 . C280 . H2801 . 121.0 no C291 . C281 . C271 . 121(3) yes C291 . C281 . H2811 . 119.7 no C271 . C281 . H2811 . 119.3 no C280 . C270 . C260 . 117(2) yes C280 . C270 . H2701 . 117.7 no C260 . C270 . H2701 . 124.7 no C281 . C271 . C261 . 120(2) yes C281 . C271 . H2711 . 121.6 no C261 . C271 . H2711 . 118.4 no C270 . C260 . C310 . 123.5(18) yes C270 . C260 . H2601 . 116.6 no C310 . C260 . H2601 . 118.9 no C271 . C261 . C311 . 119.5(17) yes C271 . C261 . H2611 . 116.5 no C311 . C261 . H2611 . 122.9 no C260 . C310 . C300 . 117.0(17) yes C260 . C310 . H3101 . 117.6 no C300 . C310 . H3101 . 124.5 no C261 . C311 . C301 . 118.9(14) yes C261 . C311 . H3101 . 171.4 no C301 . C311 . H3101 . 69.4 no C261 . C311 . H3111 . 117.7 no C301 . C311 . H3111 . 123.2 no C310 . C300 . C290 . 120.0(20) yes C310 . C300 . H3001 . 115.8 no C290 . C300 . H3001 . 124.1 no C290 . C300 . H3011 . 175.0 no C311 . C301 . C291 . 121.1(17) yes C311 . C301 . H3011 . 119.9 no C291 . C301 . H3011 . 119.0 no _chemical_name_common RuCp*(C5H5B-CN)