Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_be4 _database_code_CSD 193648 _journal_coden_Cambridge 182 loop_ _publ_author_name 'Carmona Ernesto' 'M. M. Conejo' 'R. Fernandez' 'A. Monge' 'del Rio,D.' 'C. Ruiz' _publ_contact_author_name 'Prof Ernesto Carmona' _publ_contact_author_address ; Departamento de Quimica Inorganica-IIQ. Universidad de Sevilla-CSIC c/Americo Vespucio s/n, Isla de la Sevilla 41092 SPAIN ; _publ_contact_author_email 'GUZMAN@US.ES' _publ_requested_journal 'Chemical Communications' _publ_section_title ; Synthesis and structural characterization of Be(?5-C5Me5)(?1-C5Me4H). Evidence for ring-inversion leading to Be(?5-C5Me4H)(?1-C5Me5). ; _publ_section_abstract ; The mixed-ring beryllocene Be(C5Me5)(C5Me4H), that contains ?5-C5Me5 and ?1-C5Me4H rings, the latter bonded to the metal through the CH carbon atom (X-rays) reacts at room temperature with CNXyl (Xyl = C6H3-2,6-Me2) to give an iminoacyl product, Be(?5-C5Me4H)[C(NXyl)C5Me5] derived from the inverted beryllocene structure Be(?5-C5Me4H)(?1-C5Me5). ; _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C19 H28 Be' _chemical_formula_weight 265.42 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 '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' 'Be' 'Be' 0.0005 0.0002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.0745(5) _cell_length_b 6.6636(4) _cell_length_c 30.295(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.097(2) _cell_angle_gamma 90.00 _cell_volume 1628.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.082 _exptl_crystal_density_method ? _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.059 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker Smart CCD' _diffrn_measurement_method \w _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6690 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0541 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 29.67 _reflns_number_total 3033 _reflns_number_observed 2426 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Smart (Bruker)' _computing_cell_refinement 'Saint (Bruker)' _computing_data_reduction 'Saint (Briker)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'XP (Bruker)' _computing_publication_material 'XCIF (Bruker)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0832P)^2^+1.8639P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3033 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0844 _refine_ls_R_factor_obs 0.0672 _refine_ls_wR_factor_all 0.1746 _refine_ls_wR_factor_obs 0.1625 _refine_ls_goodness_of_fit_all 0.925 _refine_ls_goodness_of_fit_obs 0.967 _refine_ls_restrained_S_all 0.925 _refine_ls_restrained_S_obs 0.967 _refine_ls_shift/esd_max -0.293 _refine_ls_shift/esd_mean 0.010 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Be Be 0.9715(3) 0.7577(4) 0.12654(11) 0.0200(6) Uani 1 d . . C1 C 1.1626(3) 0.7077(3) 0.09269(9) 0.0222(5) Uani 1 d . . C2 C 1.2049(2) 0.8102(3) 0.13264(9) 0.0225(6) Uani 1 d . . C3 C 1.1463(2) 0.6961(3) 0.16866(8) 0.0206(5) Uani 1 d . . C4 C 1.0676(2) 0.5198(3) 0.15041(8) 0.0190(5) Uani 1 d . . C5 C 1.0780(2) 0.5271(3) 0.10403(8) 0.0197(5) Uani 1 d . . C6 C 1.2040(3) 0.7787(4) 0.04759(10) 0.0344(6) Uani 1 d . . H6A H 1.1469(18) 0.6974(18) 0.02575(10) 0.052 Uiso 1 calc R . H6B H 1.3214(4) 0.7681(26) 0.0441(2) 0.052 Uiso 1 calc R . H6C H 1.1704(21) 0.9161(9) 0.0440(2) 0.052 Uiso 1 calc R . C7 C 1.3041(3) 1.0014(3) 0.13618(10) 0.0336(7) Uani 1 d . . H7A H 1.2587(15) 1.0982(10) 0.1156(4) 0.050 Uiso 1 calc R . H7B H 1.4172(6) 0.9742(6) 0.1295(6) 0.050 Uiso 1 calc R . H7C H 1.2995(20) 1.0534(16) 0.1657(2) 0.050 Uiso 1 calc R . C8 C 1.1678(3) 0.7474(4) 0.21648(9) 0.0332(6) Uani 1 d . . H8A H 1.2793(7) 0.7173(24) 0.2265(2) 0.050 Uiso 1 calc R . H8B H 1.0916(15) 0.6701(19) 0.23315(11) 0.050 Uiso 1 calc R . H8C H 1.1465(21) 0.8878(6) 0.22057(12) 0.050 Uiso 1 calc R . C9 C 0.9859(3) 0.3601(3) 0.17728(9) 0.0269(6) Uani 1 d . . H9A H 0.9197(17) 0.4224(3) 0.1991(4) 0.040 Uiso 1 calc R . H9B H 1.0694(3) 0.2781(16) 0.1916(5) 0.040 Uiso 1 calc R . H9C H 0.9166(16) 0.2782(16) 0.15820(12) 0.040 Uiso 1 calc R . C10 C 1.0071(3) 0.3765(3) 0.07120(9) 0.0289(6) Uani 1 d . . H10A H 1.0959(3) 0.3117(19) 0.0565(4) 0.043 Uiso 1 calc R . H10B H 0.9364(17) 0.4442(5) 0.0498(3) 0.043 Uiso 1 calc R . H10C H 0.9441(18) 0.2778(15) 0.08643(11) 0.043 Uiso 1 calc R . C11 C 0.7699(2) 0.8639(3) 0.12199(8) 0.0188(5) Uani 1 d . . H11A H 0.7738(28) 1.0108(34) 0.1198(8) 0.021(6) Uiso 1 d . . C12 C 0.6986(2) 0.7661(3) 0.16058(8) 0.0193(5) Uani 1 d . . C13 C 0.6132(2) 0.5980(3) 0.14609(8) 0.0206(5) Uani 1 d . . C14 C 0.6156(2) 0.5899(3) 0.09879(8) 0.0207(5) Uani 1 d . . C15 C 0.7015(2) 0.7523(3) 0.08332(8) 0.0201(5) Uani 1 d . . C16 C 0.7181(3) 0.8434(3) 0.20690(9) 0.0303(6) Uani 1 d . . H16A H 0.6241(10) 0.9246(20) 0.2136(2) 0.045 Uiso 1 calc R . H16B H 0.8172(11) 0.9228(20) 0.2098(2) 0.045 Uiso 1 calc R . H16C H 0.7257(20) 0.7324(3) 0.22707(10) 0.045 Uiso 1 calc R . C17 C 0.5321(3) 0.4429(3) 0.17434(9) 0.0289(6) Uani 1 d . . H17A H 0.5818(15) 0.3142(6) 0.1695(4) 0.043 Uiso 1 calc R . H17B H 0.4158(5) 0.4364(19) 0.1666(4) 0.043 Uiso 1 calc R . H17C H 0.5470(19) 0.4791(14) 0.20490(10) 0.043 Uiso 1 calc R . C18 C 0.5382(3) 0.4222(3) 0.07133(10) 0.0290(6) Uani 1 d . . H18A H 0.4213(4) 0.4174(17) 0.0759(4) 0.044 Uiso 1 calc R . H18B H 0.5877(15) 0.2966(4) 0.0801(4) 0.044 Uiso 1 calc R . H18C H 0.5567(18) 0.4461(14) 0.04066(10) 0.044 Uiso 1 calc R . C19 C 0.7278(3) 0.8127(4) 0.03651(9) 0.0326(6) Uani 1 d . . H19A H 0.8394(7) 0.8596(24) 0.03387(15) 0.049 Uiso 1 calc R . H19B H 0.6518(15) 0.9180(18) 0.0282(2) 0.049 Uiso 1 calc R . H19C H 0.7092(21) 0.6992(7) 0.01746(11) 0.049 Uiso 1 calc 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 Be 0.0198(13) 0.0188(11) 0.022(2) 0.0016(9) 0.0038(12) -0.0011(9) C1 0.0170(10) 0.0246(10) 0.025(2) 0.0045(8) 0.0056(10) 0.0025(7) C2 0.0135(9) 0.0199(9) 0.034(2) 0.0013(8) 0.0010(10) -0.0006(7) C3 0.0165(10) 0.0207(9) 0.025(2) 0.0001(8) -0.0007(10) 0.0021(7) C4 0.0153(9) 0.0167(8) 0.025(2) 0.0017(7) 0.0031(9) 0.0015(6) C5 0.0166(10) 0.0206(9) 0.022(2) -0.0011(7) 0.0035(9) 0.0020(7) C6 0.0290(13) 0.0427(13) 0.032(2) 0.0108(11) 0.0135(13) 0.0041(10) C7 0.0189(10) 0.0215(10) 0.060(2) 0.0024(10) 0.0004(12) -0.0044(8) C8 0.0346(13) 0.0335(12) 0.031(2) -0.0061(10) -0.0059(12) 0.0052(9) C9 0.0251(11) 0.0220(9) 0.034(2) 0.0059(9) 0.0066(11) 0.0004(8) C10 0.0284(12) 0.0294(11) 0.029(2) -0.0088(9) 0.0017(11) 0.0017(8) C11 0.0163(9) 0.0165(8) 0.024(2) 0.0016(7) 0.0026(9) 0.0000(6) C12 0.0164(10) 0.0210(9) 0.021(2) -0.0004(7) 0.0039(9) 0.0021(7) C13 0.0153(10) 0.0181(9) 0.029(2) 0.0026(8) 0.0047(10) 0.0015(6) C14 0.0140(9) 0.0203(9) 0.028(2) -0.0009(8) 0.0012(10) 0.0008(6) C15 0.0164(10) 0.0230(9) 0.021(2) 0.0023(8) 0.0012(9) 0.0016(7) C16 0.0275(12) 0.0346(12) 0.029(2) -0.0034(9) 0.0050(11) 0.0024(9) C17 0.0227(11) 0.0277(10) 0.037(2) 0.0086(9) 0.0067(11) -0.0029(8) C18 0.0245(11) 0.0278(10) 0.035(2) -0.0059(9) -0.0004(11) -0.0032(8) C19 0.0308(13) 0.0405(13) 0.027(2) 0.0057(10) 0.0026(12) -0.0014(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Be C11 1.776(3) . ? Be C4 1.896(3) . ? Be C5 1.899(3) . ? Be C3 1.912(4) . ? Be C2 1.919(3) . ? Be C1 1.913(4) . ? C1 C2 1.421(3) . ? C1 C5 1.432(3) . ? C1 C6 1.495(4) . ? C2 C3 1.425(3) . ? C2 C7 1.506(3) . ? C3 C4 1.437(3) . ? C3 C8 1.493(4) . ? C4 C5 1.411(3) . ? C4 C9 1.506(3) . ? C5 C10 1.511(3) . ? C11 C12 1.474(3) . ? C11 C15 1.478(3) . ? C12 C13 1.379(3) . ? C12 C16 1.498(3) . ? C13 C14 1.435(4) . ? C13 C17 1.507(3) . ? C14 C15 1.377(3) . ? C14 C18 1.514(3) . ? C15 C19 1.497(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 Be C4 136.4(2) . . ? C11 Be C5 136.1(2) . . ? C4 Be C5 43.66(12) . . ? C11 Be C3 142.1(2) . . ? C4 Be C3 44.32(10) . . ? C5 Be C3 74.52(13) . . ? C11 Be C2 146.0(2) . . ? C4 Be C2 74.30(13) . . ? C5 Be C2 74.11(13) . . ? C3 Be C2 43.68(12) . . ? C11 Be C1 141.5(2) . . ? C4 Be C1 74.47(13) . . ? C5 Be C1 44.11(11) . . ? C3 Be C1 74.36(14) . . ? C2 Be C1 43.53(12) . . ? C2 C1 C5 107.6(2) . . ? C2 C1 C6 124.8(2) . . ? C5 C1 C6 127.6(2) . . ? C2 C1 Be 68.5(2) . . ? C5 C1 Be 67.45(14) . . ? C6 C1 Be 130.3(2) . . ? C1 C2 C3 108.6(2) . . ? C1 C2 C7 125.3(2) . . ? C3 C2 C7 126.0(2) . . ? C1 C2 Be 68.00(15) . . ? C3 C2 Be 67.90(15) . . ? C7 C2 Be 132.7(2) . . ? C2 C3 C4 107.3(2) . . ? C2 C3 C8 126.2(2) . . ? C4 C3 C8 126.5(2) . . ? C2 C3 Be 68.4(2) . . ? C4 C3 Be 67.26(14) . . ? C8 C3 Be 131.0(2) . . ? C5 C4 C3 108.2(2) . . ? C5 C4 C9 127.3(2) . . ? C3 C4 C9 124.5(2) . . ? C5 C4 Be 68.29(15) . . ? C3 C4 Be 68.42(14) . . ? C9 C4 Be 128.0(2) . . ? C4 C5 C1 108.3(2) . . ? C4 C5 C10 126.7(2) . . ? C1 C5 C10 124.9(2) . . ? C4 C5 Be 68.05(15) . . ? C1 C5 Be 68.44(14) . . ? C10 C5 Be 127.4(2) . . ? C12 C11 C15 105.1(2) . . ? C12 C11 Be 98.4(2) . . ? C15 C11 Be 100.1(2) . . ? C13 C12 C11 108.2(2) . . ? C13 C12 C16 127.7(2) . . ? C11 C12 C16 124.1(2) . . ? C12 C13 C14 108.9(2) . . ? C12 C13 C17 126.8(2) . . ? C14 C13 C17 124.3(2) . . ? C15 C14 C13 109.6(2) . . ? C15 C14 C18 126.6(2) . . ? C13 C14 C18 123.8(2) . . ? C14 C15 C11 107.7(2) . . ? C14 C15 C19 128.7(2) . . ? C11 C15 C19 123.6(2) . . ? _refine_diff_density_max 0.282 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.048