# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Carsten Strohmann' _publ_contact_author_address ; Institut fuer Anorganische Chemie Universitaet Wuerzburg Am Hubland 97074 Wuerzburg Germany ; _publ_contact_author_email mail@carsten-strohmann.de _publ_contact_author_fax '0049 931 888 4605' _publ_contact_author_phone '0049 931 888 4613' _journal_volume ? _journal_page_first ? _journal_page_last ? _journal_year ? loop_ _publ_author_name 'Carsten Strohmann' 'Christian Daeschlein' data_vi290906 _database_code_depnum_ccdc_archive 'CCDC 666392' _audit_creation_date 2007-11-05T21:02:38-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C23 H48 Li N5 Si' _chemical_formula_weight 429.69 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.714(4) _cell_length_b 9.9895(12) _cell_length_c 19.355(4) _cell_angle_alpha 90 _cell_angle_beta 99.07(3) _cell_angle_gamma 90 _cell_volume 2809.4(10) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.016 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.1 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'FACEIT in IPDS (Stoe & Cie, 1999)' _exptl_absorpt_correction_T_min 0.4746 _exptl_absorpt_correction_T_max 0.8300 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_method 'phi scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% none _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_unetI/netI 0.0295 _diffrn_reflns_number 28705 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.3 _diffrn_reflns_theta_max 27 _diffrn_reflns_theta_full 27 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_total 6091 _reflns_number_gt 4745 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Expose in IPDS (Stoe & Cie, 1999)' _computing_cell_refinement 'Cell in IPDS (Stoe & Cie, 1999)' _computing_data_reduction 'Integrate in IPDS (Stoe & Cie, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Schakal99 (Keller, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0794P)^2^+0.2150P] 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 riding _refine_ls_extinction_method none _refine_ls_number_reflns 6091 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.122 _refine_ls_wR_factor_gt 0.1147 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.245 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.035 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.69328(8) 0.17697(12) 0.60268(6) 0.0354(2) Uani 1 1 d . . . C2 C 0.68900(9) 0.31661(12) 0.59687(7) 0.0390(3) Uani 1 1 d . . . H2 H 0.7392 0.3684 0.6195 0.047 Uiso 1 1 calc R . . C3 C 0.61325(10) 0.38213(14) 0.55888(7) 0.0466(3) Uani 1 1 d . . . H3 H 0.6128 0.4771 0.5559 0.056 Uiso 1 1 calc R . . C4 C 0.53893(10) 0.30978(16) 0.52566(8) 0.0501(3) Uani 1 1 d . . . H4 H 0.4873 0.3544 0.5 0.06 Uiso 1 1 calc R . . C5 C 0.54057(10) 0.17217(16) 0.53019(8) 0.0535(4) Uani 1 1 d . . . H5 H 0.4899 0.1214 0.5075 0.064 Uiso 1 1 calc R . . C6 C 0.61647(9) 0.10714(14) 0.56801(7) 0.0460(3) Uani 1 1 d . . . H6 H 0.6162 0.0122 0.5704 0.055 Uiso 1 1 calc R . . C7 C 0.80393(12) -0.19389(14) 0.65274(8) 0.0513(3) Uani 1 1 d . . . H7A H 0.8226 -0.1797 0.7036 0.062 Uiso 1 1 calc R . . H7B H 0.8527 -0.2473 0.6358 0.062 Uiso 1 1 calc R . . C8 C 0.7151(2) -0.2731(2) 0.64099(12) 0.0962(8) Uani 1 1 d . . . H8A H 0.6682 -0.2258 0.6624 0.144 Uiso 1 1 calc R . . H8B H 0.7257 -0.3618 0.6623 0.144 Uiso 1 1 calc R . . H8C H 0.6939 -0.2828 0.5907 0.144 Uiso 1 1 calc R . . C9 C 0.80253(10) -0.07241(13) 0.54354(7) 0.0442(3) Uani 1 1 d . . . H9A H 0.7868 0.0166 0.5224 0.053 Uiso 1 1 calc R . . H9B H 0.7555 -0.1366 0.5214 0.053 Uiso 1 1 calc R . . C10 C 0.89585(12) -0.11476(18) 0.52628(9) 0.0608(4) Uani 1 1 d . . . H10A H 0.9433 -0.0529 0.5485 0.091 Uiso 1 1 calc R . . H10B H 0.8941 -0.1129 0.4755 0.091 Uiso 1 1 calc R . . H10C H 0.9101 -0.2057 0.5437 0.091 Uiso 1 1 calc R . . C11 C 0.90940(10) 0.24389(14) 0.59678(7) 0.0456(3) Uani 1 1 d . . . H11A H 0.856 0.2341 0.559 0.055 Uiso 1 1 calc R . . H11B H 0.9597 0.1873 0.5844 0.055 Uiso 1 1 calc R . . C12 C 0.94076(13) 0.38955(18) 0.59940(10) 0.0672(5) Uani 1 1 d . . . H12A H 0.8906 0.4471 0.6097 0.101 Uiso 1 1 calc R . . H12B H 0.9575 0.4148 0.5541 0.101 Uiso 1 1 calc R . . H12C H 0.9943 0.4003 0.6361 0.101 Uiso 1 1 calc R . . C13 C 0.96172(9) 0.18359(13) 0.71870(7) 0.0430(3) Uani 1 1 d . . . H13A H 0.9376 0.1666 0.7628 0.052 Uiso 1 1 calc R . . H13B H 0.9939 0.2709 0.7236 0.052 Uiso 1 1 calc R . . C14 C 1.03181(10) 0.07499(15) 0.70989(9) 0.0541(4) Uani 1 1 d . . . H14A H 1.0012 -0.0124 0.7055 0.081 Uiso 1 1 calc R . . H14B H 1.0805 0.0746 0.7508 0.081 Uiso 1 1 calc R . . H14C H 1.0588 0.093 0.6677 0.081 Uiso 1 1 calc R . . C15 C 0.77435(16) -0.20638(18) 0.84347(10) 0.0717(5) Uani 1 1 d . . . H15A H 0.7601 -0.2799 0.8736 0.107 Uiso 1 1 calc R . . H15B H 0.8411 -0.1925 0.85 0.107 Uiso 1 1 calc R . . H15C H 0.7521 -0.2289 0.7944 0.107 Uiso 1 1 calc R . . C16 C 0.76456(17) -0.0531(2) 0.93572(9) 0.0745(5) Uani 1 1 d . . . H16A H 0.7507 -0.1278 0.9652 0.112 Uiso 1 1 calc R . . H16B H 0.7353 0.0286 0.9496 0.112 Uiso 1 1 calc R . . H16C H 0.8313 -0.0399 0.9414 0.112 Uiso 1 1 calc R . . C17 C 0.62816(13) -0.10457(17) 0.85003(10) 0.0653(5) Uani 1 1 d . . . H17A H 0.6121 -0.1689 0.8851 0.078 Uiso 1 1 calc R . . H17B H 0.6095 -0.1444 0.8031 0.078 Uiso 1 1 calc R . . C18 C 0.57547(12) 0.02359(18) 0.85485(10) 0.0627(4) Uani 1 1 d . . . H18A H 0.5088 0.0037 0.8484 0.075 Uiso 1 1 calc R . . H18B H 0.5933 0.0631 0.902 0.075 Uiso 1 1 calc R . . C19 C 0.53126(12) 0.0990(2) 0.73503(10) 0.0683(5) Uani 1 1 d . . . H19A H 0.4675 0.1125 0.7423 0.103 Uiso 1 1 calc R . . H19B H 0.5387 0.0074 0.7187 0.103 Uiso 1 1 calc R . . H19C H 0.5461 0.1626 0.6999 0.103 Uiso 1 1 calc R . . C20 C 0.58695(11) 0.25900(16) 0.82601(10) 0.0581(4) Uani 1 1 d . . . H20A H 0.5336 0.2665 0.8512 0.07 Uiso 1 1 calc R . . H20B H 0.5762 0.3199 0.7852 0.07 Uiso 1 1 calc R . . C21 C 0.67350(12) 0.30201(16) 0.87417(9) 0.0577(4) Uani 1 1 d . . . H21A H 0.6687 0.3981 0.8856 0.069 Uiso 1 1 calc R . . H21B H 0.679 0.2506 0.9184 0.069 Uiso 1 1 calc R . . C22 C 0.75893(13) 0.37437(15) 0.78392(9) 0.0579(4) Uani 1 1 d . . . H22A H 0.7052 0.3594 0.7478 0.087 Uiso 1 1 calc R . . H22B H 0.8153 0.3599 0.7639 0.087 Uiso 1 1 calc R . . H22C H 0.7579 0.4664 0.8013 0.087 Uiso 1 1 calc R . . C23 C 0.84046(14) 0.2997(2) 0.89343(9) 0.0744(5) Uani 1 1 d . . . H23A H 0.8947 0.2859 0.8707 0.112 Uiso 1 1 calc R . . H23B H 0.8413 0.2353 0.9317 0.112 Uiso 1 1 calc R . . H23C H 0.8414 0.3909 0.9122 0.112 Uiso 1 1 calc R . . Li Li 0.73637(15) 0.0871(2) 0.79281(11) 0.0393(4) Uani 1 1 d . . . N1 N 0.79753(8) -0.06517(10) 0.61803(5) 0.0384(2) Uani 1 1 d . . . N2 N 0.88360(7) 0.19399(11) 0.66176(5) 0.0373(2) Uani 1 1 d . . . N3 N 0.72906(10) -0.08327(12) 0.86204(7) 0.0525(3) Uani 1 1 d . . . N4 N 0.59371(8) 0.12094(13) 0.80151(6) 0.0484(3) Uani 1 1 d . . . N5 N 0.75642(9) 0.28044(12) 0.84197(6) 0.0481(3) Uani 1 1 d . . . Si Si 0.78797(2) 0.08461(3) 0.665829(16) 0.03246(10) Uani 1 1 d . . . 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 C1 0.0377(6) 0.0400(6) 0.0284(5) -0.0015(4) 0.0051(4) 0.0029(5) C2 0.0425(6) 0.0397(6) 0.0356(6) 0.0005(5) 0.0087(5) 0.0043(5) C3 0.0517(7) 0.0438(7) 0.0461(7) 0.0061(6) 0.0134(6) 0.0129(6) C4 0.0445(7) 0.0612(9) 0.0433(7) 0.0064(6) 0.0034(6) 0.0172(6) C5 0.0450(7) 0.0601(9) 0.0506(8) -0.0056(6) -0.0078(6) 0.0052(6) C6 0.0447(7) 0.0432(7) 0.0462(7) -0.0021(5) -0.0049(6) 0.0020(5) C7 0.0715(9) 0.0386(7) 0.0450(7) 0.0024(6) 0.0127(7) 0.0089(6) C8 0.145(2) 0.0716(12) 0.0674(12) 0.0059(10) 0.0036(13) -0.0534(14) C9 0.0574(8) 0.0439(7) 0.0313(6) -0.0057(5) 0.0069(5) 0.0032(6) C10 0.0695(10) 0.0632(9) 0.0539(9) -0.0092(7) 0.0227(8) 0.0064(8) C11 0.0446(7) 0.0540(8) 0.0401(7) 0.0028(6) 0.0120(6) -0.0020(6) C12 0.0662(10) 0.0635(10) 0.0723(11) 0.0145(8) 0.0121(9) -0.0161(8) C13 0.0401(6) 0.0452(7) 0.0413(7) -0.0055(5) -0.0005(5) 0.0000(5) C14 0.0474(8) 0.0511(8) 0.0609(9) 0.0001(7) -0.0010(7) 0.0070(6) C15 0.1063(15) 0.0550(9) 0.0591(10) 0.0112(8) 0.0301(10) 0.0205(9) C16 0.1101(16) 0.0716(11) 0.0428(8) 0.0082(8) 0.0147(9) 0.0192(10) C17 0.0801(12) 0.0518(9) 0.0713(11) 0.0090(8) 0.0343(9) -0.0099(8) C18 0.0611(9) 0.0632(9) 0.0711(10) 0.0116(8) 0.0332(8) -0.0052(8) C19 0.0489(8) 0.0842(12) 0.0701(11) 0.0003(9) 0.0040(8) -0.0060(8) C20 0.0589(9) 0.0557(9) 0.0654(10) 0.0035(7) 0.0272(8) 0.0108(7) C21 0.0779(10) 0.0508(8) 0.0514(8) -0.0092(6) 0.0313(8) -0.0013(7) C22 0.0791(11) 0.0452(7) 0.0548(9) -0.0062(6) 0.0273(8) -0.0115(7) C23 0.0802(12) 0.0936(14) 0.0481(9) -0.0231(9) 0.0065(8) -0.0216(10) Li 0.0453(11) 0.0409(10) 0.0330(10) -0.0004(8) 0.0100(8) -0.0021(9) N1 0.0499(6) 0.0361(5) 0.0289(5) -0.0005(4) 0.0049(4) 0.0034(4) N2 0.0376(5) 0.0432(5) 0.0305(5) -0.0014(4) 0.0041(4) -0.0002(4) N3 0.0691(8) 0.0486(6) 0.0432(6) 0.0087(5) 0.0196(6) 0.0071(6) N4 0.0460(6) 0.0517(6) 0.0500(7) 0.0047(5) 0.0151(5) -0.0020(5) N5 0.0606(7) 0.0494(6) 0.0369(6) -0.0104(5) 0.0160(5) -0.0101(5) Si 0.03604(17) 0.03561(17) 0.02564(16) -0.00066(11) 0.00466(12) 0.00168(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 C2 1.4000(17) . ? C1 C6 1.4054(18) . ? C1 Si 1.9364(13) . ? C2 C3 1.3974(18) . ? C3 C4 1.382(2) . ? C4 C5 1.377(2) . ? C5 C6 1.3956(19) . ? C7 N1 1.4470(17) . ? C7 C8 1.514(3) . ? C9 N1 1.4570(16) . ? C9 C10 1.523(2) . ? C11 N2 1.4577(17) . ? C11 C12 1.525(2) . ? C13 N2 1.4654(16) . ? C13 C14 1.5248(19) . ? C15 N3 1.470(2) . ? C16 N3 1.471(2) . ? C17 N3 1.481(2) . ? C17 C18 1.507(3) . ? C18 N4 1.473(2) . ? C19 N4 1.475(2) . ? C20 N4 1.467(2) . ? C20 C21 1.517(3) . ? C21 N5 1.471(2) . ? C22 N5 1.469(2) . ? C23 N5 1.473(2) . ? Li N5 2.153(2) . ? Li N4 2.159(3) . ? Li N3 2.179(2) . ? Li Si 2.684(2) . ? N1 Si 1.7764(11) . ? N2 Si 1.7930(11) . ? 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 C2 C1 C6 115.70(11) . . ? C2 C1 Si 122.97(9) . . ? C6 C1 Si 120.61(10) . . ? C3 C2 C1 122.07(12) . . ? C4 C3 C2 120.45(13) . . ? C5 C4 C3 119.19(12) . . ? C4 C5 C6 120.16(14) . . ? C5 C6 C1 122.43(13) . . ? N1 C7 C8 113.78(15) . . ? N1 C9 C10 114.75(12) . . ? N2 C11 C12 114.59(13) . . ? N2 C13 C14 115.50(11) . . ? N3 C17 C18 112.39(14) . . ? N4 C18 C17 111.40(13) . . ? N4 C20 C21 111.83(13) . . ? N5 C21 C20 111.73(13) . . ? N5 Li N4 83.81(9) . . ? N5 Li N3 116.46(11) . . ? N4 Li N3 86.06(9) . . ? N5 Li Si 111.98(9) . . ? N4 Li Si 119.46(10) . . ? N3 Li Si 127.17(10) . . ? C7 N1 C9 113.93(11) . . ? C7 N1 Si 120.75(9) . . ? C9 N1 Si 125.29(8) . . ? C11 N2 C13 113.14(11) . . ? C11 N2 Si 124.00(9) . . ? C13 N2 Si 116.85(9) . . ? C15 N3 C16 107.65(14) . . ? C15 N3 C17 108.86(15) . . ? C16 N3 C17 112.06(15) . . ? C15 N3 Li 115.78(11) . . ? C16 N3 Li 113.05(12) . . ? C17 N3 Li 99.27(11) . . ? C20 N4 C18 111.40(13) . . ? C20 N4 C19 110.91(13) . . ? C18 N4 C19 110.86(14) . . ? C20 N4 Li 106.78(11) . . ? C18 N4 Li 103.78(11) . . ? C19 N4 Li 112.86(12) . . ? C22 N5 C21 110.68(13) . . ? C22 N5 C23 108.29(14) . . ? C21 N5 C23 111.00(13) . . ? C22 N5 Li 104.66(10) . . ? C21 N5 Li 104.70(11) . . ? C23 N5 Li 117.28(13) . . ? N1 Si N2 111.30(6) . . ? N1 Si C1 100.41(5) . . ? N2 Si C1 99.98(5) . . ? N1 Si Li 122.81(6) . . ? N2 Si Li 111.82(6) . . ? C1 Si Li 107.11(6) . . ? # Attachment 'compound_3.cif' data_do210305 _database_code_depnum_ccdc_archive 'CCDC 666393' _audit_creation_date 2007-11-05T14:59:59-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C22 H36 Li N3 Si' _chemical_formula_weight 377.57 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 18.287(4) _cell_length_b 58.069(12) _cell_length_c 9.1042(18) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 9668(3) _cell_formula_units_Z 16 _cell_measurement_temperature 173(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.038 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3296 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'FACEIT in IPDS (Stoe & Cie, 1999)' _exptl_absorpt_correction_T_min 0.3528 _exptl_absorpt_correction_T_max 0.7707 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_method 'phi scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% none _diffrn_reflns_av_R_equivalents 0.0766 _diffrn_reflns_av_unetI/netI 0.06 _diffrn_reflns_number 10457 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -68 _diffrn_reflns_limit_k_max 68 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 3915 _reflns_number_gt 3350 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Expose in IPDS (Stoe & Cie, 1999)' _computing_cell_refinement 'Cell in IPDS (Stoe & Cie, 1999)' _computing_data_reduction 'Integrate in IPDS (Stoe & Cie, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Schakal99 (Keller, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0980P)^2^+0.0000P] 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 riding _refine_ls_extinction_method none _refine_ls_number_reflns 3915 _refine_ls_number_parameters 250 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.1488 _refine_ls_wR_factor_gt 0.1442 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.23(16) _refine_diff_density_max 0.251 _refine_diff_density_min -0.24 _refine_diff_density_rms 0.044 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 '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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0810(2) 0.02970(5) 0.8879(4) 0.0578(8) Uani 1 1 d . . . H1A H 1.1302 0.0314 0.9292 0.087 Uiso 1 1 calc R . . H1B H 1.084 0.0295 0.7804 0.087 Uiso 1 1 calc R . . H1C H 1.0595 0.0152 0.9225 0.087 Uiso 1 1 calc R . . C2 C 1.03646(17) 0.05424(5) 1.1608(4) 0.0464(7) Uani 1 1 d . . . C3 C 1.04015(19) 0.03367(5) 1.2387(4) 0.0556(8) Uani 1 1 d . . . H3 H 1.0378 0.0196 1.1857 0.067 Uiso 1 1 calc R . . C4 C 1.0471(2) 0.03274(6) 1.3898(5) 0.0667(10) Uani 1 1 d . . . H4 H 1.0491 0.0183 1.4381 0.08 Uiso 1 1 calc R . . C5 C 1.0511(2) 0.05302(6) 1.4714(4) 0.0673(10) Uani 1 1 d . . . H5 H 1.0558 0.0526 1.5753 0.081 Uiso 1 1 calc R . . C6 C 1.0480(2) 0.07391(6) 1.3966(4) 0.0626(9) Uani 1 1 d . . . H6 H 1.0509 0.0879 1.4499 0.075 Uiso 1 1 calc R . . C7 C 1.0407(2) 0.07443(5) 1.2473(4) 0.0531(8) Uani 1 1 d . . . H7 H 1.0385 0.089 1.1995 0.064 Uiso 1 1 calc R . . C8 C 1.08200(16) 0.08134(4) 0.8970(3) 0.0423(6) Uani 1 1 d . . . C9 C 1.14577(18) 0.08719(5) 0.9710(4) 0.0540(8) Uani 1 1 d . . . H9 H 1.1611 0.0779 1.051 0.065 Uiso 1 1 calc R . . C10 C 1.1883(2) 0.10622(6) 0.9325(4) 0.0601(8) Uani 1 1 d . . . H10 H 1.2306 0.11 0.988 0.072 Uiso 1 1 calc R . . C11 C 1.1684(2) 0.11949(5) 0.8137(4) 0.0560(8) Uani 1 1 d . . . H11 H 1.1969 0.1325 0.7867 0.067 Uiso 1 1 calc R . . C12 C 1.1069(2) 0.11374(5) 0.7345(4) 0.0571(8) Uani 1 1 d . . . H12 H 1.0939 0.1225 0.6505 0.068 Uiso 1 1 calc R . . C13 C 1.06376(19) 0.09518(5) 0.7766(4) 0.0519(8) Uani 1 1 d . . . H13 H 1.0208 0.0918 0.7221 0.062 Uiso 1 1 calc R . . C14 C 0.8848(2) 0.10686(5) 1.0227(5) 0.0726(11) Uani 1 1 d . . . H14A H 0.8616 0.1192 1.0792 0.109 Uiso 1 1 calc R . . H14B H 0.9092 0.1134 0.9365 0.109 Uiso 1 1 calc R . . H14C H 0.9208 0.0989 1.0843 0.109 Uiso 1 1 calc R . . C15 C 0.7751(2) 0.10283(6) 0.8844(6) 0.0770(12) Uani 1 1 d . . . H15A H 0.7366 0.0922 0.8521 0.116 Uiso 1 1 calc R . . H15B H 0.7996 0.1094 0.7984 0.116 Uiso 1 1 calc R . . H15C H 0.7533 0.1152 0.9428 0.116 Uiso 1 1 calc R . . C16 C 0.7947(3) 0.07957(6) 1.1046(4) 0.0708(11) Uani 1 1 d . . . H16A H 0.7623 0.0909 1.1531 0.085 Uiso 1 1 calc R . . H16B H 0.8335 0.0752 1.1752 0.085 Uiso 1 1 calc R . . C17 C 0.7505(2) 0.05823(6) 1.0642(5) 0.0685(10) Uani 1 1 d . . . H17A H 0.7252 0.0523 1.1525 0.082 Uiso 1 1 calc R . . H17B H 0.7131 0.0623 0.9902 0.082 Uiso 1 1 calc R . . C18 C 0.8303(3) 0.02601(6) 1.1233(5) 0.0726(11) Uani 1 1 d . . . H18A H 0.7907 0.0175 1.1716 0.109 Uiso 1 1 calc R . . H18B H 0.8544 0.036 1.1949 0.109 Uiso 1 1 calc R . . H18C H 0.8659 0.0151 1.0831 0.109 Uiso 1 1 calc R . . C19 C 0.7625(2) 0.02569(6) 0.8936(5) 0.0639(10) Uani 1 1 d . . . H19A H 0.7121 0.0224 0.9274 0.077 Uiso 1 1 calc R . . H19B H 0.7886 0.0108 0.8834 0.077 Uiso 1 1 calc R . . C20 C 0.7595(2) 0.03775(5) 0.7439(5) 0.0629(9) Uani 1 1 d . . . H20A H 0.7374 0.0272 0.6708 0.076 Uiso 1 1 calc R . . H20B H 0.7278 0.0515 0.7514 0.076 Uiso 1 1 calc R . . C21 C 0.8767(2) 0.02454(6) 0.6508(5) 0.0697(10) Uani 1 1 d . . . H21A H 0.8536 0.0168 0.5672 0.105 Uiso 1 1 calc R . . H21B H 0.8798 0.0138 0.7339 0.105 Uiso 1 1 calc R . . H21C H 0.926 0.0296 0.6231 0.105 Uiso 1 1 calc R . . C22 C 0.8266(3) 0.06023(7) 0.5661(5) 0.0723(10) Uani 1 1 d . . . H22A H 0.8757 0.0647 0.5333 0.108 Uiso 1 1 calc R . . H22B H 0.7991 0.074 0.5942 0.108 Uiso 1 1 calc R . . H22C H 0.8011 0.0523 0.4861 0.108 Uiso 1 1 calc R . . Li Li 0.8791(3) 0.05942(8) 0.8864(6) 0.0470(11) Uani 1 1 d . . . N1 N 0.82854(15) 0.09028(4) 0.9744(3) 0.0558(7) Uani 1 1 d . . . N2 N 0.80001(16) 0.04005(4) 1.0036(3) 0.0557(7) Uani 1 1 d . . . N3 N 0.83261(15) 0.04474(4) 0.6932(3) 0.0533(6) Uani 1 1 d . . . Si Si 1.02041(5) 0.055336(12) 0.95053(9) 0.0438(2) Uani 1 1 d . . . 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 C1 0.072(2) 0.0406(14) 0.0603(19) -0.0038(13) -0.0033(17) 0.0128(14) C2 0.0400(16) 0.0488(15) 0.0503(18) 0.0034(12) -0.0026(14) -0.0009(11) C3 0.0563(19) 0.0487(16) 0.062(2) 0.0095(14) 0.0025(17) -0.0036(13) C4 0.059(2) 0.068(2) 0.073(3) 0.0291(18) 0.0047(19) 0.0014(17) C5 0.068(2) 0.082(2) 0.052(2) 0.0083(17) 0.0001(19) 0.0013(17) C6 0.067(2) 0.0658(19) 0.054(2) -0.0037(16) 0.0029(19) 0.0011(17) C7 0.062(2) 0.0500(16) 0.0474(19) 0.0005(13) 0.0005(15) 0.0010(13) C8 0.0444(16) 0.0380(12) 0.0446(16) -0.0032(11) 0.0019(13) 0.0025(11) C9 0.0462(17) 0.0586(16) 0.0574(19) 0.0078(15) -0.0011(16) -0.0034(13) C10 0.056(2) 0.0646(18) 0.060(2) -0.0011(16) -0.0003(18) -0.0089(15) C11 0.056(2) 0.0488(15) 0.063(2) -0.0035(15) 0.0083(18) -0.0051(14) C12 0.061(2) 0.0527(15) 0.057(2) 0.0120(14) 0.0083(17) 0.0097(14) C13 0.0504(19) 0.0539(16) 0.0514(19) 0.0000(14) -0.0043(15) 0.0029(13) C14 0.082(3) 0.0459(16) 0.090(3) -0.0131(17) -0.011(2) 0.0047(16) C15 0.075(3) 0.0535(18) 0.102(3) -0.0001(19) -0.018(2) 0.0161(17) C16 0.087(3) 0.0582(18) 0.067(2) -0.0097(17) 0.013(2) 0.0170(18) C17 0.059(2) 0.068(2) 0.078(3) 0.0072(19) 0.021(2) 0.0038(17) C18 0.088(3) 0.0588(19) 0.072(2) 0.0182(18) 0.008(2) -0.0021(18) C19 0.0489(19) 0.0520(16) 0.091(3) 0.0059(17) -0.0006(18) -0.0121(14) C20 0.0531(19) 0.0532(16) 0.083(3) -0.0080(17) -0.0116(19) -0.0033(14) C21 0.071(3) 0.0598(19) 0.078(2) -0.0123(17) 0.001(2) 0.0029(17) C22 0.077(3) 0.079(2) 0.061(2) 0.0095(19) -0.012(2) -0.0027(19) Li 0.045(3) 0.041(2) 0.055(3) -0.001(2) -0.001(2) -0.0029(19) N1 0.0567(16) 0.0411(11) 0.0698(19) -0.0053(12) -0.0024(15) 0.0074(11) N2 0.0542(16) 0.0443(12) 0.0687(18) 0.0076(12) 0.0100(14) -0.0013(11) N3 0.0510(15) 0.0499(12) 0.0591(16) -0.0015(12) -0.0087(14) -0.0018(10) Si 0.0441(4) 0.0381(3) 0.0493(4) -0.0019(3) -0.0054(4) 0.0016(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 Si 1.942(3) . ? C2 C3 1.391(4) . ? C2 C7 1.415(5) . ? C2 Si 1.938(3) . ? C3 C4 1.382(5) . ? C4 C5 1.395(6) . ? C5 C6 1.392(5) . ? C6 C7 1.366(5) . ? C8 C9 1.389(5) . ? C8 C13 1.400(4) . ? C8 Si 1.946(3) . ? C9 C10 1.396(5) . ? C10 C11 1.376(5) . ? C11 C12 1.377(5) . ? C12 C13 1.390(5) . ? C14 N1 1.475(5) . ? C15 N1 1.469(5) . ? C16 N1 1.474(5) . ? C16 C17 1.524(6) . ? C16 Li 2.774(6) . ? C17 N2 1.496(5) . ? C18 N2 1.469(5) . ? C19 N2 1.473(5) . ? C19 C20 1.533(6) . ? C20 N3 1.472(5) . ? C21 N3 1.475(4) . ? C22 N3 1.470(5) . ? Li N2 2.120(6) . ? Li N3 2.131(6) . ? Li N1 2.170(5) . ? Li Si 2.660(5) . ? 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 C3 C2 C7 115.2(3) . . ? C3 C2 Si 122.6(3) . . ? C7 C2 Si 122.0(2) . . ? C4 C3 C2 123.1(3) . . ? C3 C4 C5 120.1(3) . . ? C6 C5 C4 118.2(4) . . ? C7 C6 C5 120.7(4) . . ? C6 C7 C2 122.7(3) . . ? C9 C8 C13 116.1(3) . . ? C9 C8 Si 123.6(2) . . ? C13 C8 Si 120.2(2) . . ? C8 C9 C10 122.6(3) . . ? C11 C10 C9 119.6(3) . . ? C10 C11 C12 119.4(3) . . ? C11 C12 C13 120.5(3) . . ? C12 C13 C8 121.7(3) . . ? N1 C16 C17 111.8(3) . . ? N1 C16 Li 50.90(17) . . ? C17 C16 Li 77.3(2) . . ? N2 C17 C16 110.0(3) . . ? N2 C19 C20 111.2(2) . . ? N3 C20 C19 111.8(3) . . ? N2 Li N3 86.1(2) . . ? N2 Li N1 87.8(2) . . ? N3 Li N1 117.7(3) . . ? N2 Li Si 120.3(2) . . ? N3 Li Si 122.2(2) . . ? N1 Li Si 114.0(2) . . ? N2 Li C16 58.94(17) . . ? N3 Li C16 122.6(3) . . ? N1 Li C16 31.82(13) . . ? Si Li C16 114.9(2) . . ? C15 N1 C16 112.2(3) . . ? C15 N1 C14 107.8(3) . . ? C16 N1 C14 109.2(3) . . ? C15 N1 Li 119.2(3) . . ? C16 N1 Li 97.3(2) . . ? C14 N1 Li 110.6(3) . . ? C18 N2 C19 111.5(3) . . ? C18 N2 C17 110.2(3) . . ? C19 N2 C17 111.6(3) . . ? C18 N2 Li 114.3(3) . . ? C19 N2 Li 106.0(3) . . ? C17 N2 Li 102.9(2) . . ? C22 N3 C20 110.4(3) . . ? C22 N3 C21 108.8(3) . . ? C20 N3 C21 111.1(3) . . ? C22 N3 Li 115.7(2) . . ? C20 N3 Li 102.3(3) . . ? C21 N3 Li 108.5(3) . . ? C2 Si C1 100.28(14) . . ? C2 Si C8 100.68(13) . . ? C1 Si C8 101.02(15) . . ? C2 Si Li 111.53(16) . . ? C1 Si Li 123.95(15) . . ? C8 Si Li 115.98(13) . . ? # Attachment 'compound_2.cif' #------------------------------------------------------------------------- #1 Global data block identification for start of deposition data_ch281106 _database_code_depnum_ccdc_archive 'CCDC 666394' _audit_creation_date 2007-11-05T12:28:25-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C17 H34 Li N3 Si' _chemical_formula_weight 315.5 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.245(3) _cell_length_b 8.9641(17) _cell_length_c 27.585(4) _cell_angle_alpha 90 _cell_angle_beta 102.091(17) _cell_angle_gamma 90 _cell_volume 4169.6(12) _cell_formula_units_Z 8 _cell_measurement_temperature 193(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.005 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'FACEIT in IPDS (Stoe & Cie, 1999)' _exptl_absorpt_correction_T_min 0.2454 _exptl_absorpt_correction_T_max 0.7038 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_method 'phi scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% none _diffrn_reflns_av_R_equivalents 0.0706 _diffrn_reflns_av_unetI/netI 0.0798 _diffrn_reflns_number 12084 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3674 _reflns_number_gt 2011 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Expose in IPDS (Stoe & Cie, 1999)' _computing_cell_refinement 'Cell in IPDS (Stoe & Cie, 1999)' _computing_data_reduction 'Integrate in IPDS (Stoe & Cie, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Schakal99 (Keller, 1999)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+0.0000P] 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 riding _refine_ls_extinction_method none _refine_ls_number_reflns 3674 _refine_ls_number_parameters 206 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0976 _refine_ls_R_factor_gt 0.051 _refine_ls_wR_factor_ref 0.1168 _refine_ls_wR_factor_gt 0.1062 _refine_ls_goodness_of_fit_ref 1.01 _refine_ls_restrained_S_all 1.01 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.201 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.04 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 '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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.54515(17) 0.3582(3) 0.06930(10) 0.0551(7) Uani 1 1 d . . . H1A H 0.5975 0.3109 0.0747 0.083 Uiso 1 1 calc R . . H1B H 0.5513 0.4669 0.069 0.083 Uiso 1 1 calc R . . H1C H 0.5132 0.3254 0.0374 0.083 Uiso 1 1 calc R . . C2 C 0.56989(18) 0.3595(3) 0.18023(10) 0.0564(7) Uani 1 1 d . . . H2A H 0.5515 0.3277 0.2099 0.085 Uiso 1 1 calc R . . H2B H 0.5764 0.4681 0.1807 0.085 Uiso 1 1 calc R . . H2C H 0.6208 0.3117 0.1797 0.085 Uiso 1 1 calc R . . C3 C 0.50531(14) 0.0896(3) 0.12251(10) 0.0439(6) Uani 1 1 d . . . C4 C 0.48956(17) 0.0053(3) 0.07861(11) 0.0558(7) Uani 1 1 d . . . H4 H 0.4783 0.0565 0.0478 0.067 Uiso 1 1 calc R . . C5 C 0.4898(2) -0.1478(4) 0.07831(14) 0.0693(9) Uani 1 1 d . . . H5 H 0.4793 -0.1997 0.0476 0.083 Uiso 1 1 calc R . . C6 C 0.50492(19) -0.2265(4) 0.12174(16) 0.0735(10) Uani 1 1 d . . . H6 H 0.5038 -0.3325 0.1214 0.088 Uiso 1 1 calc R . . C7 C 0.52181(18) -0.1502(3) 0.16606(13) 0.0628(9) Uani 1 1 d . . . H7 H 0.5331 -0.2034 0.1965 0.075 Uiso 1 1 calc R . . C8 C 0.52237(15) 0.0047(3) 0.16620(10) 0.0514(7) Uani 1 1 d . . . H8 H 0.5348 0.0552 0.1971 0.062 Uiso 1 1 calc R . . C9 C 0.20289(18) 0.4547(4) 0.03016(11) 0.0764(10) Uani 1 1 d . . . H9A H 0.1658 0.4432 0.0524 0.115 Uiso 1 1 calc R . . H9B H 0.2087 0.3591 0.0141 0.115 Uiso 1 1 calc R . . H9C H 0.1825 0.5297 0.0049 0.115 Uiso 1 1 calc R . . C10 C 0.33357(17) 0.5284(3) 0.02474(10) 0.0589(8) Uani 1 1 d . . . H10A H 0.3114 0.606 0.0008 0.088 Uiso 1 1 calc R . . H10B H 0.3397 0.4358 0.007 0.088 Uiso 1 1 calc R . . H10C H 0.3855 0.5606 0.0436 0.088 Uiso 1 1 calc R . . C11 C 0.27285(19) 0.6411(3) 0.08660(10) 0.0592(8) Uani 1 1 d . . . H11A H 0.2368 0.7112 0.065 0.071 Uiso 1 1 calc R . . H11B H 0.3255 0.6892 0.0961 0.071 Uiso 1 1 calc R . . C12 C 0.2412(2) 0.6100(4) 0.13253(11) 0.0651(9) Uani 1 1 d . . . H12A H 0.2325 0.7054 0.1486 0.078 Uiso 1 1 calc R . . H12B H 0.1896 0.558 0.1232 0.078 Uiso 1 1 calc R . . C13 C 0.3559(2) 0.6106(4) 0.20000(11) 0.0759(10) Uani 1 1 d . . . H13A H 0.3818 0.6756 0.1796 0.114 Uiso 1 1 calc R . . H13B H 0.3957 0.547 0.2208 0.114 Uiso 1 1 calc R . . H13C H 0.3294 0.6718 0.2211 0.114 Uiso 1 1 calc R . . C14 C 0.25584(19) 0.4187(4) 0.19716(10) 0.0629(8) Uani 1 1 d . . . H14A H 0.2133 0.4757 0.208 0.075 Uiso 1 1 calc R . . H14B H 0.2939 0.3851 0.2272 0.075 Uiso 1 1 calc R . . C15 C 0.22031(16) 0.2847(4) 0.16793(10) 0.0607(8) Uani 1 1 d . . . H15A H 0.1965 0.2187 0.1896 0.073 Uiso 1 1 calc R . . H15B H 0.1774 0.3179 0.1403 0.073 Uiso 1 1 calc R . . C16 C 0.2393(2) 0.0919(4) 0.11094(13) 0.0864(12) Uani 1 1 d . . . H16A H 0.2087 0.0217 0.1267 0.13 Uiso 1 1 calc R . . H16B H 0.2792 0.037 0.0974 0.13 Uiso 1 1 calc R . . H16C H 0.2036 0.1445 0.0841 0.13 Uiso 1 1 calc R . . C17 C 0.3336(2) 0.1193(4) 0.18687(12) 0.0726(9) Uani 1 1 d . . . H17A H 0.3034 0.0537 0.2045 0.109 Uiso 1 1 calc R . . H17B H 0.3639 0.1911 0.2102 0.109 Uiso 1 1 calc R . . H17C H 0.3702 0.0594 0.1721 0.109 Uiso 1 1 calc R . . Li Li 0.3437(3) 0.3686(5) 0.11958(15) 0.0448(10) Uani 1 1 d . . . N1 N 0.28003(12) 0.5026(3) 0.05877(7) 0.0493(6) Uani 1 1 d . . . N2 N 0.29706(13) 0.5170(3) 0.16772(7) 0.0500(6) Uani 1 1 d . . . N3 N 0.27885(13) 0.1999(3) 0.14765(7) 0.0508(6) Uani 1 1 d . . . Si Si 0.49286(4) 0.30224(9) 0.12186(3) 0.0414(2) Uani 1 1 d . . . 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 C1 0.0539(18) 0.0595(18) 0.0543(17) 0.0032(13) 0.0167(13) 0.0017(14) C2 0.0586(19) 0.0574(18) 0.0521(17) -0.0077(14) 0.0090(13) 0.0031(15) C3 0.0289(14) 0.0550(17) 0.0479(15) -0.0002(13) 0.0080(11) 0.0002(12) C4 0.0559(18) 0.056(2) 0.0543(18) -0.0095(14) 0.0092(13) -0.0060(15) C5 0.071(2) 0.062(2) 0.077(2) -0.0220(18) 0.0207(17) -0.0109(17) C6 0.056(2) 0.050(2) 0.114(3) -0.009(2) 0.0191(19) -0.0005(16) C7 0.0481(19) 0.056(2) 0.082(2) 0.0167(17) 0.0081(15) 0.0082(15) C8 0.0435(16) 0.0554(19) 0.0533(17) 0.0008(14) 0.0057(12) 0.0034(14) C9 0.0536(19) 0.115(3) 0.0543(19) 0.0104(19) -0.0033(14) -0.006(2) C10 0.0601(18) 0.078(2) 0.0405(15) 0.0105(14) 0.0139(12) -0.0016(17) C11 0.064(2) 0.0623(19) 0.0518(17) 0.0140(14) 0.0126(14) 0.0231(15) C12 0.072(2) 0.070(2) 0.0563(19) 0.0063(15) 0.0185(15) 0.0311(17) C13 0.100(3) 0.077(2) 0.0495(19) -0.0139(16) 0.0130(17) -0.009(2) C14 0.0611(19) 0.091(2) 0.0413(16) 0.0009(15) 0.0209(13) 0.0092(17) C15 0.0411(15) 0.094(2) 0.0491(16) 0.0119(17) 0.0146(12) -0.0056(17) C16 0.105(3) 0.084(3) 0.069(2) -0.0136(19) 0.015(2) -0.039(2) C17 0.071(2) 0.082(2) 0.067(2) 0.0204(18) 0.0222(17) 0.0114(19) Li 0.044(2) 0.051(2) 0.038(2) -0.0003(19) 0.0057(18) 0.002(2) N1 0.0422(13) 0.0672(15) 0.0367(11) 0.0060(11) 0.0041(9) 0.0039(11) N2 0.0515(13) 0.0625(15) 0.0375(12) -0.0002(11) 0.0128(10) 0.0070(12) N3 0.0516(14) 0.0644(15) 0.0377(12) 0.0044(12) 0.0126(9) -0.0071(13) Si 0.0377(4) 0.0486(4) 0.0381(4) -0.0006(4) 0.0081(3) 0.0020(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C1 Si 1.927(3) . ? C2 Si 1.930(3) . ? C3 C8 1.403(4) . ? C3 C4 1.405(4) . ? C3 Si 1.918(3) . ? C4 C5 1.373(4) . ? C5 C6 1.368(5) . ? C6 C7 1.378(5) . ? C7 C8 1.388(4) . ? C9 N1 1.462(4) . ? C10 N1 1.466(3) . ? C11 N1 1.478(4) . ? C11 C12 1.507(4) . ? C12 N2 1.474(3) . ? C13 N2 1.465(4) . ? C14 N2 1.477(4) . ? C14 C15 1.504(4) . ? C15 N3 1.465(4) . ? C16 N3 1.462(4) . ? C17 N3 1.468(4) . ? Li N3 2.121(5) . ? Li N2 2.151(5) . ? Li N1 2.166(5) . ? Li Si 2.628(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 C8 C3 C4 114.6(3) . . ? C8 C3 Si 123.4(2) . . ? C4 C3 Si 121.7(2) . . ? C5 C4 C3 122.9(3) . . ? C6 C5 C4 120.7(3) . . ? C5 C6 C7 119.1(3) . . ? C6 C7 C8 120.0(3) . . ? C7 C8 C3 122.7(3) . . ? N1 C11 C12 111.4(2) . . ? N2 C12 C11 110.9(2) . . ? N2 C14 C15 111.8(2) . . ? N3 C15 C14 112.5(2) . . ? N3 Li N2 85.52(18) . . ? N3 Li N1 117.3(2) . . ? N2 Li N1 86.61(18) . . ? N3 Li Si 114.70(19) . . ? N2 Li Si 128.01(19) . . ? N1 Li Si 118.60(19) . . ? C9 N1 C10 108.9(2) . . ? C9 N1 C11 111.2(2) . . ? C10 N1 C11 109.4(2) . . ? C9 N1 Li 120.8(2) . . ? C10 N1 Li 107.4(2) . . ? C11 N1 Li 98.49(19) . . ? C13 N2 C12 110.5(3) . . ? C13 N2 C14 111.0(2) . . ? C12 N2 C14 112.1(2) . . ? C13 N2 Li 115.4(2) . . ? C12 N2 Li 102.72(19) . . ? C14 N2 Li 104.8(2) . . ? C16 N3 C15 110.4(2) . . ? C16 N3 C17 108.6(3) . . ? C15 N3 C17 111.3(2) . . ? C16 N3 Li 115.1(2) . . ? C15 N3 Li 103.1(2) . . ? C17 N3 Li 108.2(2) . . ? C3 Si C1 101.35(12) . . ? C3 Si C2 101.55(12) . . ? C1 Si C2 102.10(13) . . ? C3 Si Li 109.40(13) . . ? C1 Si Li 122.20(13) . . ? C2 Si Li 117.32(13) . . ?