# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef 'compound3_4.CIF' #============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Dr. Hans-Georg Stammler ; _publ_contact_author_phone '49 521 1066165' _publ_contact_author_fax '49 521 1066146' _publ_contact_author_email georg.stammler@uni-bielefeld.de _publ_requested_coeditor_name ? _publ_contact_letter ; Please consider this CIF submission for deposition To: deposit@ccdc.cam.ac.uk Subject: Depositing Crystal Structure Data Dear Madam or Sir, please find enclosed the crystallographic data of compound3 'C32 H54 Cl2 Li2 N8 Y2' compound4 'C21.50 H33 N4 Y' for deposition in your data file. With kind regards Beate Neumann ; #============================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_issue ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Two different product types from reactions of lithiated cyclic aminals with organoyttrium chlorides ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address B.J.Hellmann ; Lehrstuhl f\"ur Anorganische Chemie und Strukturchemie Universit\"at Bielefeld Universit\"atsstrasse 15 33615 Bielefeld Germany ; I.Kamps ; Lehrstuhl f\"ur Anorganische Chemie und Strukturchemie Universit\"at Bielefeld Universit\"atsstrasse 15 33615 Bielefeld Germany ; B.Neumann ; Lehrstuhl f\"ur Anorganische Chemie und Strukturchemie Universit\"at Bielefeld Universit\"atsstrasse 15 33615 Bielefeld Germany ; H.-G.Stammler ; Lehrstuhl f\"ur Anorganische Chemie und Strukturchemie Universit\"at Bielefeld Universit\"atsstrasse 15 33615 Bielefeld Germany ; N.W.Mitzel ; Lehrstuhl f\"ur Anorganische Chemie und Strukturchemie Universit\"at Bielefeld Universit\"atsstrasse 15 33615 Bielefeld Germany ; _publ_contact_author_name 'Dr. Hans-Georg Stammler' #============================================================================== data_compound3 _database_code_depnum_ccdc_archive 'CCDC 778691' #TrackingRef 'compound3_4.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H54 Cl2 Li2 N8 Y2' _chemical_formula_sum 'C32 H54 Cl2 Li2 N8 Y2' _chemical_formula_weight 813.43 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Y Y -2.7962 3.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 8.47700(10) _cell_length_b 21.3447(4) _cell_length_c 10.8024(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.8503(11) _cell_angle_gamma 90.00 _cell_volume 1880.26(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 41558 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description rhomb _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 3.246 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5926 _exptl_absorpt_correction_T_max 0.8545 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(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_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 42960 _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4288 _reflns_number_gt 3789 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0308P)^2^+0.5233P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4288 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0306 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0588 _refine_ls_wR_factor_gt 0.0562 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 Y1 Y 0.339364(18) 0.119819(7) 0.280572(14) 0.01494(6) Uani 1 1 d . . . Cl1 Cl 0.61061(5) 0.06113(2) 0.40744(4) 0.02308(10) Uani 1 1 d . . . N1 N 0.29987(17) 0.16165(7) 0.48067(13) 0.0211(3) Uani 1 1 d . . . N2 N 0.07609(17) 0.11894(6) 0.32428(13) 0.0178(3) Uani 1 1 d . . . N3 N 0.07154(16) 0.00856(7) 0.27412(13) 0.0188(3) Uani 1 1 d . . . N4 N 0.29133(17) -0.03873(7) 0.21272(13) 0.0206(3) Uani 1 1 d . . . Li1 Li 0.2910(4) 0.00079(14) 0.4103(3) 0.0245(6) Uani 1 1 d . . . C1 C 0.2044(2) 0.10308(8) 0.44445(16) 0.0189(3) Uani 1 1 d . . . H1 H 0.157(2) 0.0878(9) 0.5126(18) 0.021(5) Uiso 1 1 d . . . C2 C 0.2023(2) 0.21670(9) 0.49895(18) 0.0279(4) Uani 1 1 d . . . H2A H 0.277(3) 0.2539(10) 0.521(2) 0.032(5) Uiso 1 1 d . . . H2B H 0.155(2) 0.2081(9) 0.5753(19) 0.026(5) Uiso 1 1 d . . . C3 C 0.0656(2) 0.23007(9) 0.37913(19) 0.0274(4) Uani 1 1 d . . . H3A H -0.001(2) 0.2624(9) 0.3946(18) 0.025(5) Uiso 1 1 d . . . H3B H 0.110(2) 0.2452(9) 0.311(2) 0.028(5) Uiso 1 1 d . . . C4 C -0.0336(2) 0.17162(9) 0.33520(19) 0.0248(4) Uani 1 1 d . . . H4A H -0.095(3) 0.1599(10) 0.396(2) 0.031(5) Uiso 1 1 d . . . H4B H -0.109(2) 0.1787(9) 0.2515(19) 0.025(5) Uiso 1 1 d . . . C5 C 0.4304(3) 0.15166(10) 0.60063(18) 0.0291(4) Uani 1 1 d . . . H5A H 0.509(3) 0.1863(11) 0.616(2) 0.036(6) Uiso 1 1 d . . . H5B H 0.490(3) 0.1137(10) 0.597(2) 0.036(6) Uiso 1 1 d . . . H5C H 0.388(3) 0.1497(10) 0.675(2) 0.036(6) Uiso 1 1 d . . . C6 C -0.0263(2) 0.06416(8) 0.27446(17) 0.0213(4) Uani 1 1 d . . . H6A H -0.103(2) 0.0546(8) 0.3270(17) 0.018(5) Uiso 1 1 d . . . H6B H -0.096(2) 0.0763(8) 0.1870(17) 0.012(4) Uiso 1 1 d . . . C7 C 0.1902(2) 0.01931(8) 0.19666(16) 0.0178(3) Uani 1 1 d . . . H7 H 0.125(2) 0.0225(9) 0.1018(19) 0.025(5) Uiso 1 1 d . . . C8 C -0.0395(2) -0.04484(9) 0.22828(18) 0.0249(4) Uani 1 1 d . . . H8A H -0.106(2) -0.0364(9) 0.139(2) 0.028(5) Uiso 1 1 d . . . H8B H -0.122(2) -0.0472(9) 0.2787(17) 0.023(5) Uiso 1 1 d . . . C9 C 0.0620(3) -0.10388(9) 0.23649(19) 0.0276(4) Uani 1 1 d . . . H9A H 0.114(3) -0.1130(9) 0.326(2) 0.034(6) Uiso 1 1 d . . . H9B H -0.008(3) -0.1380(10) 0.2021(19) 0.029(5) Uiso 1 1 d . . . C10 C 0.1915(2) -0.09487(9) 0.16603(18) 0.0270(4) Uani 1 1 d . . . H10A H 0.265(3) -0.1307(10) 0.179(2) 0.033(6) Uiso 1 1 d . . . H10B H 0.138(2) -0.0903(10) 0.069(2) 0.030(5) Uiso 1 1 d . . . C11 C 0.4136(2) -0.03249(10) 0.14118(18) 0.0267(4) Uani 1 1 d . . . H11A H 0.478(3) -0.0693(11) 0.151(2) 0.035(6) Uiso 1 1 d . . . H11B H 0.484(3) 0.0045(10) 0.1707(19) 0.029(5) Uiso 1 1 d . . . H11C H 0.363(2) -0.0262(10) 0.049(2) 0.033(5) Uiso 1 1 d . . . C12 C 0.3468(2) 0.14356(9) 0.03827(16) 0.0233(4) Uani 1 1 d . . . H12 H 0.313(3) 0.1101(10) -0.018(2) 0.031(6) Uiso 1 1 d . . . C13 C 0.2485(2) 0.19117(9) 0.06843(17) 0.0247(4) Uani 1 1 d . . . H13 H 0.138(3) 0.1977(10) 0.0348(19) 0.030(5) Uiso 1 1 d . . . C14 C 0.3500(2) 0.22966(9) 0.16331(18) 0.0240(4) Uani 1 1 d . . . H14 H 0.316(2) 0.2670(10) 0.1990(19) 0.030(5) Uiso 1 1 d . . . C15 C 0.5104(2) 0.20554(8) 0.19275(16) 0.0214(4) Uani 1 1 d . . . H15 H 0.606(2) 0.2229(9) 0.2571(19) 0.025(5) Uiso 1 1 d . . . C16 C 0.5086(2) 0.15241(9) 0.11525(16) 0.0214(4) Uani 1 1 d . . . H16 H 0.598(3) 0.1264(9) 0.116(2) 0.027(5) Uiso 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 Y1 0.01391(9) 0.01595(9) 0.01550(9) 0.00079(6) 0.00491(6) 0.00026(6) Cl1 0.01734(19) 0.0311(2) 0.0218(2) 0.00876(17) 0.00693(16) 0.00603(16) N1 0.0220(7) 0.0207(8) 0.0189(7) -0.0034(6) 0.0027(6) 0.0032(6) N2 0.0152(7) 0.0193(7) 0.0190(7) 0.0018(5) 0.0047(6) 0.0034(5) N3 0.0170(7) 0.0201(7) 0.0194(7) 0.0011(6) 0.0052(6) -0.0024(6) N4 0.0236(7) 0.0183(7) 0.0196(7) -0.0003(6) 0.0053(6) 0.0007(6) Li1 0.0270(15) 0.0236(16) 0.0203(15) 0.0021(12) 0.0020(12) 0.0022(12) C1 0.0185(8) 0.0225(9) 0.0156(8) 0.0018(7) 0.0046(7) 0.0025(7) C2 0.0340(10) 0.0222(10) 0.0274(10) -0.0061(8) 0.0085(8) 0.0077(8) C3 0.0314(10) 0.0239(10) 0.0288(10) 0.0001(8) 0.0115(8) 0.0122(8) C4 0.0189(8) 0.0299(10) 0.0271(10) 0.0035(8) 0.0090(8) 0.0087(7) C5 0.0318(10) 0.0311(11) 0.0197(9) -0.0057(8) -0.0011(8) 0.0051(9) C6 0.0148(8) 0.0255(10) 0.0239(9) 0.0017(7) 0.0057(7) -0.0006(7) C7 0.0183(8) 0.0182(8) 0.0166(8) 0.0021(6) 0.0044(6) 0.0011(7) C8 0.0227(9) 0.0269(10) 0.0224(9) 0.0028(7) 0.0017(7) -0.0076(8) C9 0.0338(10) 0.0198(9) 0.0246(10) 0.0020(7) 0.0000(8) -0.0087(8) C10 0.0356(11) 0.0181(9) 0.0227(10) -0.0016(7) 0.0002(8) 0.0006(8) C11 0.0318(10) 0.0264(10) 0.0247(10) -0.0017(8) 0.0126(8) 0.0065(9) C12 0.0285(9) 0.0255(10) 0.0168(8) 0.0018(7) 0.0075(7) -0.0044(8) C13 0.0204(9) 0.0279(10) 0.0239(9) 0.0103(7) 0.0028(7) 0.0009(8) C14 0.0287(9) 0.0173(9) 0.0278(9) 0.0041(7) 0.0111(8) 0.0000(7) C15 0.0206(8) 0.0225(9) 0.0220(9) 0.0038(7) 0.0070(7) -0.0060(7) C16 0.0216(8) 0.0239(9) 0.0213(9) 0.0044(7) 0.0105(7) -0.0006(7) _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 Y1 C1 2.3827(17) . ? Y1 N2 2.4041(14) . ? Y1 N1 2.4448(14) . ? Y1 C7 2.5294(17) . ? Y1 Cl1 2.6482(4) . ? Y1 C15 2.6649(17) . ? Y1 C16 2.6703(16) . ? Y1 C14 2.6780(17) . ? Y1 C13 2.6833(17) . ? Y1 C12 2.6835(17) . ? Y1 Li1 2.984(3) . ? Cl1 Li1 2.328(3) 3_656 ? Cl1 Li1 3.008(3) . ? N1 C5 1.472(2) . ? N1 C2 1.481(2) . ? N1 C1 1.483(2) . ? N2 C6 1.468(2) . ? N2 C4 1.484(2) . ? N2 C1 1.487(2) . ? N3 C6 1.448(2) . ? N3 C8 1.475(2) . ? N3 C7 1.491(2) . ? N3 Li1 2.039(3) . ? N4 C11 1.458(2) . ? N4 C10 1.474(2) . ? N4 C7 1.490(2) . ? N4 Li1 2.296(3) . ? Li1 C7 2.266(3) . ? Li1 Cl1 2.328(3) 3_656 ? Li1 C1 2.364(3) . ? C1 H1 0.983(19) . ? C2 C3 1.510(3) . ? C2 H2A 1.00(2) . ? C2 H2B 1.025(19) . ? C3 C4 1.507(3) . ? C3 H3A 0.93(2) . ? C3 H3B 0.97(2) . ? C4 H4A 0.97(2) . ? C4 H4B 0.97(2) . ? C5 H5A 0.98(2) . ? C5 H5B 0.96(2) . ? C5 H5C 0.97(2) . ? C6 H6A 0.994(18) . ? C6 H6B 1.001(17) . ? C7 H7 1.025(19) . ? C8 C9 1.515(3) . ? C8 H8A 0.99(2) . ? C8 H8B 1.000(19) . ? C9 C10 1.509(3) . ? C9 H9A 0.96(2) . ? C9 H9B 0.95(2) . ? C10 H10A 0.97(2) . ? C10 H10B 1.02(2) . ? C11 H11A 0.95(2) . ? C11 H11B 0.99(2) . ? C11 H11C 0.98(2) . ? C12 C13 1.407(3) . ? C12 C16 1.409(2) . ? C12 H12 0.93(2) . ? C13 C14 1.408(3) . ? C13 H13 0.92(2) . ? C14 C15 1.407(2) . ? C14 H14 0.96(2) . ? C15 C16 1.407(3) . ? C15 H15 0.99(2) . ? C16 H16 0.94(2) . ? 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 C1 Y1 N2 36.20(5) . . ? C1 Y1 N1 35.74(5) . . ? N2 Y1 N1 58.03(5) . . ? C1 Y1 C7 81.06(6) . . ? N2 Y1 C7 70.35(5) . . ? N1 Y1 C7 116.80(5) . . ? C1 Y1 Cl1 94.01(4) . . ? N2 Y1 Cl1 128.03(3) . . ? N1 Y1 Cl1 91.40(3) . . ? C7 Y1 Cl1 93.60(4) . . ? C1 Y1 C15 141.80(6) . . ? N2 Y1 C15 134.41(5) . . ? N1 Y1 C15 106.45(5) . . ? C7 Y1 C15 136.24(5) . . ? Cl1 Y1 C15 91.66(4) . . ? C1 Y1 C16 172.17(6) . . ? N2 Y1 C16 146.15(5) . . ? N1 Y1 C16 136.43(5) . . ? C7 Y1 C16 106.78(5) . . ? Cl1 Y1 C16 85.42(4) . . ? C15 Y1 C16 30.59(5) . . ? C1 Y1 C14 124.59(6) . . ? N2 Y1 C14 104.63(5) . . ? N1 Y1 C14 97.40(5) . . ? C7 Y1 C14 130.63(5) . . ? Cl1 Y1 C14 121.49(4) . . ? C15 Y1 C14 30.54(5) . . ? C16 Y1 C14 50.36(6) . . ? C1 Y1 C13 129.47(6) . . ? N2 Y1 C13 96.14(5) . . ? N1 Y1 C13 118.11(5) . . ? C7 Y1 C13 100.17(6) . . ? Cl1 Y1 C13 135.76(4) . . ? C15 Y1 C13 50.46(5) . . ? C16 Y1 C13 50.37(6) . . ? C14 Y1 C13 30.46(6) . . ? C1 Y1 C12 153.75(6) . . ? N2 Y1 C12 117.60(5) . . ? N1 Y1 C12 147.01(5) . . ? C7 Y1 C12 87.32(6) . . ? Cl1 Y1 C12 110.23(4) . . ? C15 Y1 C12 50.45(5) . . ? C16 Y1 C12 30.52(5) . . ? C14 Y1 C12 50.25(6) . . ? C13 Y1 C12 30.40(6) . . ? C1 Y1 Li1 50.79(7) . . ? N2 Y1 Li1 69.34(7) . . ? N1 Y1 Li1 79.98(7) . . ? C7 Y1 Li1 47.67(7) . . ? Cl1 Y1 Li1 64.24(6) . . ? C15 Y1 Li1 155.48(7) . . ? C16 Y1 Li1 134.74(7) . . ? C14 Y1 Li1 173.94(7) . . ? C13 Y1 Li1 147.18(7) . . ? C12 Y1 Li1 131.44(7) . . ? Li1 Cl1 Y1 139.99(8) 3_656 . ? Li1 Cl1 Li1 82.17(10) 3_656 . ? Y1 Cl1 Li1 63.30(6) . . ? C5 N1 C2 108.10(14) . . ? C5 N1 C1 109.59(14) . . ? C2 N1 C1 114.81(14) . . ? C5 N1 Y1 118.29(11) . . ? C2 N1 Y1 128.61(11) . . ? C1 N1 Y1 69.85(8) . . ? C6 N2 C4 108.19(13) . . ? C6 N2 C1 110.90(13) . . ? C4 N2 C1 115.33(13) . . ? C6 N2 Y1 114.94(10) . . ? C4 N2 Y1 130.17(11) . . ? C1 N2 Y1 71.12(8) . . ? C6 N3 C8 108.70(13) . . ? C6 N3 C7 110.47(13) . . ? C8 N3 C7 113.39(13) . . ? C6 N3 Li1 118.36(14) . . ? C8 N3 Li1 123.52(14) . . ? C7 N3 Li1 78.18(12) . . ? C11 N4 C10 108.53(14) . . ? C11 N4 C7 109.39(14) . . ? C10 N4 C7 112.18(14) . . ? C11 N4 Li1 129.84(14) . . ? C10 N4 Li1 118.05(13) . . ? C7 N4 Li1 69.87(11) . . ? N3 Li1 C7 40.10(8) . . ? N3 Li1 N4 65.90(10) . . ? C7 Li1 N4 38.11(7) . . ? N3 Li1 Cl1 134.57(15) . 3_656 ? C7 Li1 Cl1 155.30(15) . 3_656 ? N4 Li1 Cl1 119.11(13) . 3_656 ? N3 Li1 C1 77.08(11) . . ? C7 Li1 C1 87.19(12) . . ? N4 Li1 C1 124.31(14) . . ? Cl1 Li1 C1 116.55(13) 3_656 . ? N3 Li1 Y1 78.88(10) . . ? C7 Li1 Y1 55.60(8) . . ? N4 Li1 Y1 80.85(9) . . ? Cl1 Li1 Y1 144.80(13) 3_656 . ? C1 Li1 Y1 51.33(7) . . ? N3 Li1 Cl1 127.20(13) . . ? C7 Li1 Cl1 90.29(10) . . ? N4 Li1 Cl1 85.29(10) . . ? Cl1 Li1 Cl1 97.83(10) 3_656 . ? C1 Li1 Cl1 85.71(10) . . ? Y1 Li1 Cl1 52.46(5) . . ? N1 C1 N2 104.76(13) . . ? N1 C1 Li1 130.50(13) . . ? N2 C1 Li1 104.97(12) . . ? N1 C1 Y1 74.41(9) . . ? N2 C1 Y1 72.68(8) . . ? Li1 C1 Y1 77.88(9) . . ? N1 C1 H1 112.7(11) . . ? N2 C1 H1 112.3(11) . . ? Li1 C1 H1 90.9(11) . . ? Y1 C1 H1 168.7(11) . . ? N1 C2 C3 111.19(15) . . ? N1 C2 H2A 108.7(12) . . ? C3 C2 H2A 110.0(12) . . ? N1 C2 H2B 108.6(11) . . ? C3 C2 H2B 110.3(11) . . ? H2A C2 H2B 107.9(16) . . ? C4 C3 C2 110.18(16) . . ? C4 C3 H3A 110.9(12) . . ? C2 C3 H3A 110.2(12) . . ? C4 C3 H3B 109.5(12) . . ? C2 C3 H3B 110.5(12) . . ? H3A C3 H3B 105.5(17) . . ? N2 C4 C3 110.15(14) . . ? N2 C4 H4A 108.7(12) . . ? C3 C4 H4A 111.0(12) . . ? N2 C4 H4B 108.2(12) . . ? C3 C4 H4B 109.6(12) . . ? H4A C4 H4B 109.1(17) . . ? N1 C5 H5A 110.5(13) . . ? N1 C5 H5B 111.2(14) . . ? H5A C5 H5B 107.6(18) . . ? N1 C5 H5C 112.0(13) . . ? H5A C5 H5C 106.6(18) . . ? H5B C5 H5C 108.7(19) . . ? N3 C6 N2 111.85(13) . . ? N3 C6 H6A 107.3(10) . . ? N2 C6 H6A 111.5(11) . . ? N3 C6 H6B 113.6(10) . . ? N2 C6 H6B 106.0(10) . . ? H6A C6 H6B 106.5(14) . . ? N4 C7 N3 105.17(13) . . ? N4 C7 Li1 72.02(11) . . ? N3 C7 Li1 61.73(11) . . ? N4 C7 Y1 116.62(10) . . ? N3 C7 Y1 106.09(10) . . ? Li1 C7 Y1 76.73(9) . . ? N4 C7 H7 107.9(11) . . ? N3 C7 H7 108.0(11) . . ? Li1 C7 H7 168.5(11) . . ? Y1 C7 H7 112.5(11) . . ? N3 C8 C9 108.84(15) . . ? N3 C8 H8A 108.9(12) . . ? C9 C8 H8A 111.6(12) . . ? N3 C8 H8B 109.5(11) . . ? C9 C8 H8B 113.5(11) . . ? H8A C8 H8B 104.3(15) . . ? C10 C9 C8 110.14(15) . . ? C10 C9 H9A 109.2(14) . . ? C8 C9 H9A 109.0(13) . . ? C10 C9 H9B 111.2(12) . . ? C8 C9 H9B 109.4(13) . . ? H9A C9 H9B 107.7(17) . . ? N4 C10 C9 111.09(15) . . ? N4 C10 H10A 107.6(13) . . ? C9 C10 H10A 110.5(13) . . ? N4 C10 H10B 108.9(12) . . ? C9 C10 H10B 110.4(11) . . ? H10A C10 H10B 108.2(17) . . ? N4 C11 H11A 109.7(13) . . ? N4 C11 H11B 110.8(11) . . ? H11A C11 H11B 110.4(17) . . ? N4 C11 H11C 111.9(12) . . ? H11A C11 H11C 107.8(17) . . ? H11B C11 H11C 106.1(17) . . ? C13 C12 C16 107.98(16) . . ? C13 C12 Y1 74.79(10) . . ? C16 C12 Y1 74.22(9) . . ? C13 C12 H12 127.7(14) . . ? C16 C12 H12 124.1(14) . . ? Y1 C12 H12 113.9(13) . . ? C12 C13 C14 107.92(16) . . ? C12 C13 Y1 74.81(10) . . ? C14 C13 Y1 74.57(10) . . ? C12 C13 H13 128.4(13) . . ? C14 C13 H13 123.7(13) . . ? Y1 C13 H13 116.6(12) . . ? C15 C14 C13 108.13(16) . . ? C15 C14 Y1 74.22(10) . . ? C13 C14 Y1 74.98(10) . . ? C15 C14 H14 125.9(12) . . ? C13 C14 H14 125.9(12) . . ? Y1 C14 H14 119.0(12) . . ? C16 C15 C14 107.91(16) . . ? C16 C15 Y1 74.92(10) . . ? C14 C15 Y1 75.24(10) . . ? C16 C15 H15 126.6(11) . . ? C14 C15 H15 125.5(11) . . ? Y1 C15 H15 115.5(11) . . ? C15 C16 C12 108.05(16) . . ? C15 C16 Y1 74.50(9) . . ? C12 C16 Y1 75.26(10) . . ? C15 C16 H16 126.3(13) . . ? C12 C16 H16 125.6(13) . . ? Y1 C16 H16 114.8(12) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.521 _refine_diff_density_min -0.464 _refine_diff_density_rms 0.061 #============================================================================== data_compound4 _database_code_depnum_ccdc_archive 'CCDC 778692' #TrackingRef 'compound3_4.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H29 N4 Y, 0.5 (C7 H8)' _chemical_formula_sum 'C21.50 H33 N4 Y' _chemical_formula_weight 436.43 # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.500 -0.015 0.500 391.2 92.3 2 1.000 -0.022 0.500 391.2 92.3 _platon_squeeze_details ; ; loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Y Y -0.2670 2.0244 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/m' _symmetry_space_group_name_Hall '-C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 25.8849(19) _cell_length_b 12.5835(9) _cell_length_c 17.2346(13) _cell_angle_alpha 90.00 _cell_angle_beta 129.264(3) _cell_angle_gamma 90.00 _cell_volume 4346.3(6) _cell_formula_units_Z 8 _cell_measurement_temperature 225(2) _cell_measurement_reflns_used 352 _cell_measurement_theta_min 6.2816 _cell_measurement_theta_max 40.1903 _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1832 _exptl_absorpt_coefficient_mu 3.855 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2818 _exptl_absorpt_correction_T_max 0.7741 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 225(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'I\mS Incoatec Microfocus' _diffrn_radiation_monochromator 'Quazar Montel multilayer optic Montel200' _diffrn_measurement_device_type 'Bruker AXS X8 Prospector Ultra with APEX II' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27268 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0151 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 5.14 _diffrn_reflns_theta_max 72.19 _reflns_number_total 4337 _reflns_number_gt 4117 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Instrument Service v2009, 11, 1, 0' _computing_cell_refinement 'APEX2 v2009.11-0 (Bruker AXS)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Highly disordered toluene was squeezed. 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^)+(0.0420P)^2^+2.8608P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4337 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0272 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0735 _refine_ls_wR_factor_gt 0.0727 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.001 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 Y1 Y 0.122928(3) 0.5000 0.309275(4) 0.04598(2) Uani 1 2 d S . . N1 N 0.21985(2) 0.59391(4) 0.32538(3) 0.05303(15) Uani 1 1 d . . . N2 N 0.14617(3) 0.5000 0.17739(4) 0.0507(2) Uani 1 2 d S . . N3 N 0.21732(4) 0.5000 0.46922(5) 0.0701(3) Uani 1 2 d S . . C1 C 0.26193(4) 0.5000 0.38044(6) 0.0592(3) Uani 1 2 d S . . H1A H 0.3025 0.5000 0.3863 0.071 Uiso 1 2 calc SR . . C2 C 0.19017(2) 0.59302(5) 0.22007(4) 0.05558(18) Uani 1 1 d . . . H2A H 0.2247 0.5868 0.2129 0.067 Uiso 1 1 calc R . . H2B H 0.1647 0.6583 0.1867 0.067 Uiso 1 1 calc R . . C3 C 0.27899(5) 0.5000 0.48233(6) 0.0732(4) Uani 1 2 d S . . H3A H 0.3055 0.4369 0.5202 0.088 Uiso 0.50 1 calc PR . . H3B H 0.3055 0.5631 0.5202 0.088 Uiso 0.50 1 calc PR . . C4 C 0.25679(3) 0.69316(5) 0.37357(5) 0.0735(3) Uani 1 1 d . . . H4A H 0.2278 0.7533 0.3358 0.110 Uiso 1 1 calc R . . H4B H 0.2950 0.6959 0.3753 0.110 Uiso 1 1 calc R . . H4C H 0.2720 0.6958 0.4414 0.110 Uiso 1 1 calc R . . C5 C 0.10277(4) 0.5000 0.06751(5) 0.0686(3) Uani 1 2 d S . . H5A H 0.0748 0.5629 0.0416 0.103 Uiso 0.50 1 calc PR . . H5B H 0.0749 0.4370 0.0416 0.103 Uiso 0.50 1 calc PR . . H5C H 0.1300 0.5001 0.0468 0.103 Uiso 1 2 calc SR . . C6 C 0.23025(6) 0.5000 0.56159(7) 0.0930(5) Uani 1 2 d S . . H6A H 0.1884 0.5000 0.5500 0.139 Uiso 1 2 calc SR . . H6B H 0.2557 0.5629 0.5993 0.139 Uiso 0.50 1 calc PR . . H6C H 0.2557 0.4371 0.5993 0.139 Uiso 0.50 1 calc PR . . C7A C 0.04071(2) 0.33264(4) 0.18543(4) 0.0702(5) Uani 0.5500(5) 1 d PG . 1 H7A H 0.0271 0.3312 0.1203 0.084 Uiso 0.5500(5) 1 calc PR . 1 C8A C 0.09870(3) 0.28360(6) 0.27152(4) 0.0603(4) Uani 0.5500(5) 1 d PG . 1 H8A H 0.1303 0.2440 0.2734 0.072 Uiso 0.5500(5) 1 calc PR . 1 C9A C 0.10063(4) 0.30494(8) 0.35424(4) 0.0627(4) Uani 0.5500(5) 1 d PG . 1 H9A H 0.1337 0.2819 0.4205 0.075 Uiso 0.5500(5) 1 calc PR . 1 C10A C 0.04384(5) 0.36717(9) 0.31926(6) 0.0782(4) Uani 0.5500(5) 1 d PG . 1 H10A H 0.0327 0.3926 0.3583 0.094 Uiso 0.5500(5) 1 calc PR . 1 C11A C 0.00680(3) 0.38429(7) 0.21494(5) 0.0828(6) Uani 0.5500(5) 1 d PG . 1 H11A H -0.0331 0.4230 0.1728 0.099 Uiso 0.5500(5) 1 calc PR . 1 C7B C 0.06941(3) 0.30331(5) 0.22014(4) 0.0612(4) Uani 0.4500(5) 1 d PG . 2 H7B H 0.0763 0.2814 0.1751 0.073 Uiso 0.4500(5) 1 calc PR . 2 C8B C 0.11226(4) 0.28218(8) 0.32465(5) 0.0658(5) Uani 0.4500(5) 1 d PG . 2 H8B H 0.1525 0.2438 0.3610 0.079 Uiso 0.4500(5) 1 calc PR . 2 C9B C 0.08369(6) 0.32917(11) 0.36464(6) 0.0699(5) Uani 0.4500(5) 1 d PG . 2 H9B H 0.1017 0.3274 0.4321 0.084 Uiso 0.4500(5) 1 calc PR . 2 C10B C 0.02319(6) 0.37934(10) 0.28484(9) 0.0757(6) Uani 0.4500(5) 1 d PG . 2 H10B H -0.0059 0.4166 0.2902 0.091 Uiso 0.4500(5) 1 calc PR . 2 C11B C 0.01436(4) 0.36335(7) 0.19553(7) 0.0623(5) Uani 0.4500(5) 1 d PG . 2 H11B H -0.0216 0.3882 0.1314 0.075 Uiso 0.4500(5) 1 calc PR . 2 Y2 Y 0.349547(2) 0.5000 0.997701(4) 0.04163(2) Uani 1 2 d S . . N4 N 0.393321(16) 0.59385(4) 1.16523(3) 0.04996(14) Uani 1 1 d . . . N5 N 0.47473(2) 0.5000 1.17536(4) 0.04893(19) Uani 1 2 d S . . N6 N 0.27052(3) 0.5000 1.01394(5) 0.0633(2) Uani 1 2 d S . . C12 C 0.37096(3) 0.5000 1.18819(5) 0.0556(2) Uani 1 2 d S . . H12A H 0.3891 0.5000 1.2589 0.067 Uiso 1 2 calc SR . . C13 C 0.46448(2) 0.59292(4) 1.21526(3) 0.05152(16) Uani 1 1 d . . . H13A H 0.4908 0.5869 1.2880 0.062 Uiso 1 1 calc R . . H13B H 0.4775 0.6581 1.2005 0.062 Uiso 1 1 calc R . . C14 C 0.29465(3) 0.5000 1.11555(5) 0.0644(3) Uani 1 2 d S . . H14A H 0.2781 0.4369 1.1271 0.077 Uiso 0.50 1 calc PR . . H14B H 0.2781 0.5631 1.1271 0.077 Uiso 0.50 1 calc PR . . C15 C 0.37490(3) 0.69371(5) 1.18659(4) 0.0698(2) Uani 1 1 d . . . H15A H 0.3270 0.6955 1.1491 0.105 Uiso 1 1 calc R . . H15B H 0.3881 0.7534 1.1670 0.105 Uiso 1 1 calc R . . H15C H 0.3975 0.6981 1.2577 0.105 Uiso 1 1 calc R . . C16 C 0.54166(3) 0.5000 1.20458(7) 0.0702(3) Uani 1 2 d S . . H16A H 0.5472 0.4369 1.1782 0.105 Uiso 0.50 1 calc PR . . H16B H 0.5749 0.5002 1.2771 0.105 Uiso 1 2 calc SR . . H16C H 0.5471 0.5628 1.1778 0.105 Uiso 0.50 1 calc PR . . C17 C 0.20053(4) 0.5000 0.94407(7) 0.0774(4) Uani 1 2 d S . . H17A H 0.1863 0.5024 0.8768 0.116 Uiso 1 2 calc SR . . H17B H 0.1834 0.5617 0.9551 0.116 Uiso 0.50 1 calc PR . . H17C H 0.1835 0.4359 0.9521 0.116 Uiso 0.50 1 calc PR . . C18A C 0.30161(2) 0.69916(4) 0.92042(3) 0.0495(3) Uani 0.5500(5) 1 d PG . 1 H18A H 0.2696 0.7238 0.9255 0.059 Uiso 0.5500(5) 1 calc PR . 1 C19A C 0.37153(2) 0.71652(6) 0.99129(4) 0.0560(4) Uani 0.5500(5) 1 d PG . 1 H19A H 0.3939 0.7547 1.0516 0.067 Uiso 0.5500(5) 1 calc PR . 1 C20A C 0.40168(3) 0.66610(7) 0.95513(7) 0.0647(4) Uani 0.5500(5) 1 d PG . 1 H20A H 0.4475 0.6650 0.9873 0.078 Uiso 0.5500(5) 1 calc PR . 1 C21A C 0.35041(4) 0.61758(7) 0.86190(7) 0.0619(3) Uani 0.5500(5) 1 d PG . 1 H21A H 0.3564 0.5788 0.8215 0.074 Uiso 0.5500(5) 1 calc PR . 1 C22A C 0.28857(3) 0.63801(6) 0.84047(4) 0.0591(4) Uani 0.5500(5) 1 d PG . 1 H22A H 0.2464 0.6151 0.7834 0.071 Uiso 0.5500(5) 1 calc PR . 1 C18B C 0.32342(3) 0.71562(5) 0.95713(4) 0.0691(5) Uani 0.4500(5) 1 d PG . 2 H18B H 0.3126 0.7528 0.9924 0.083 Uiso 0.4500(5) 1 calc PR . 2 C19B C 0.38859(3) 0.70056(7) 0.98865(6) 0.0817(6) Uani 0.4500(5) 1 d PG . 2 H19B H 0.4285 0.7260 1.0485 0.098 Uiso 0.4500(5) 1 calc PR . 2 C20B C 0.38296(6) 0.64036(9) 0.91393(9) 0.0763(5) Uani 0.4500(5) 1 d PG . 2 H20B H 0.4184 0.6189 0.9156 0.092 Uiso 0.4500(5) 1 calc PR . 2 C21B C 0.31432(6) 0.61822(9) 0.83622(7) 0.0698(4) Uani 0.4500(5) 1 d PG . 2 H21B H 0.2964 0.5796 0.7774 0.084 Uiso 0.4500(5) 1 calc PR . 2 C22B C 0.27752(4) 0.66473(7) 0.86294(5) 0.0569(4) Uani 0.4500(5) 1 d PG . 2 H22B H 0.2310 0.6622 0.8249 0.068 Uiso 0.4500(5) 1 calc PR . 2 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 Y1 0.05528(2) 0.03251(3) 0.03441(2) 0.000 0.02093(1) 0.000 N1 0.05459(16) 0.0361(2) 0.04480(15) -0.00178(15) 0.02026(12) -0.00499(16) N2 0.0616(2) 0.0393(3) 0.03969(19) 0.000 0.02660(14) 0.000 N3 0.0774(4) 0.0563(4) 0.0412(3) 0.000 0.0207(2) 0.000 C1 0.0481(3) 0.0461(4) 0.0519(3) 0.000 0.0168(2) 0.000 C2 0.06487(19) 0.0426(3) 0.05124(17) 0.00180(19) 0.03295(13) -0.0027(2) C3 0.0691(4) 0.0514(5) 0.0452(4) 0.000 0.0106(3) 0.000 C4 0.0726(3) 0.0459(3) 0.0664(3) -0.0084(3) 0.0271(2) -0.0161(3) C5 0.0856(4) 0.0606(5) 0.0429(3) 0.000 0.0328(2) 0.000 C6 0.1361(7) 0.0600(6) 0.0597(4) 0.000 0.0510(3) 0.000 C7A 0.0583(5) 0.0495(6) 0.0594(5) 0.0036(4) 0.0168(4) -0.0128(4) C8A 0.0618(4) 0.0392(5) 0.0590(4) -0.0053(4) 0.0283(3) -0.0098(4) C9A 0.0770(4) 0.0488(5) 0.0566(3) 0.0122(4) 0.0396(2) 0.0031(4) C10A 0.0892(4) 0.0473(6) 0.1230(5) 0.0040(5) 0.0789(3) 0.0000(4) C11A 0.0747(5) 0.0436(6) 0.1027(7) -0.0045(5) 0.0432(4) -0.0097(5) C7B 0.0725(5) 0.0419(6) 0.0572(4) -0.0145(4) 0.0354(3) -0.0210(5) C8B 0.0792(5) 0.0396(6) 0.0686(5) 0.0105(5) 0.0421(4) -0.0035(5) C9B 0.0861(5) 0.0552(8) 0.0824(5) 0.0050(5) 0.0600(3) -0.0042(5) C10B 0.0818(6) 0.0559(8) 0.0780(6) -0.0080(6) 0.0451(4) -0.0204(6) C11B 0.0537(5) 0.0326(5) 0.0599(6) 0.0032(5) 0.0167(4) -0.0044(5) Y2 0.04603(2) 0.03361(3) 0.04547(2) 0.000 0.02905(1) 0.000 N4 0.05794(13) 0.0399(2) 0.05710(14) -0.00315(14) 0.03880(9) 0.00237(14) N5 0.05132(18) 0.0364(3) 0.0591(2) 0.000 0.03494(13) 0.000 N6 0.0619(2) 0.0657(4) 0.0728(2) 0.000 0.04758(14) 0.000 C12 0.0681(2) 0.0550(4) 0.0584(2) 0.000 0.04705(14) 0.000 C13 0.05464(17) 0.0417(3) 0.05168(17) -0.00527(18) 0.03057(11) -0.00321(18) C14 0.0704(2) 0.0630(5) 0.0826(3) 0.000 0.05918(15) 0.000 C15 0.0832(2) 0.0545(3) 0.0821(2) -0.0101(2) 0.05723(14) 0.0071(2) C16 0.0560(3) 0.0539(5) 0.0998(4) 0.000 0.0489(2) 0.000 C17 0.0713(3) 0.0709(6) 0.0936(4) 0.000 0.0538(2) 0.000 C18A 0.0475(3) 0.0408(5) 0.0486(3) 0.0041(3) 0.0249(2) 0.0091(3) C19A 0.0491(4) 0.0356(4) 0.0546(4) 0.0059(4) 0.0192(3) -0.0014(3) C20A 0.0632(3) 0.0406(5) 0.0855(4) 0.0147(4) 0.0449(3) -0.0031(4) C21A 0.0773(3) 0.0429(5) 0.0897(3) 0.0132(3) 0.0644(2) 0.0035(3) C22A 0.0692(4) 0.0425(5) 0.0443(3) 0.0037(4) 0.0259(3) -0.0016(4) C18B 0.1063(8) 0.0334(5) 0.0299(4) -0.0095(4) 0.0251(4) -0.0053(6) C19B 0.0911(7) 0.0531(8) 0.0727(6) 0.0130(6) 0.0385(5) -0.0137(6) C20B 0.0610(4) 0.0723(8) 0.0941(6) 0.0307(6) 0.0483(3) -0.0001(5) C21B 0.1271(5) 0.0416(6) 0.0677(3) 0.0152(4) 0.0744(3) 0.0321(5) C22B 0.0703(5) 0.0366(6) 0.0477(4) 0.0002(4) 0.0296(3) 0.0106(4) _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 Y1 N3 2.2457(6) . ? Y1 N1 2.6241(6) . ? Y1 N1 2.6241(6) 6_565 ? Y1 N2 2.6942(8) . ? Y1 C10A 2.731(2) 6_565 ? Y1 C10A 2.7314(11) . ? Y1 C9A 2.7431(17) 6_565 ? Y1 C9A 2.7431 . ? Y1 C11A 2.7591 . ? Y1 C11A 2.7591(19) 6_565 ? Y1 C7B 2.7769 . ? Y1 C7B 2.7769 6_565 ? N1 C2 1.4559(8) . ? N1 C4 1.4692(8) . ? N1 C1 1.4748(6) . ? N2 C2 1.4656(6) . ? N2 C2 1.4656(6) 6_565 ? N2 C5 1.4682(9) . ? N3 C6 1.4043(16) . ? N3 C3 1.4638(17) . ? C1 N1 1.4748(6) 6_565 ? C1 C3 1.5156(16) . ? C1 H1A 0.9900 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C4 H4C 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C5 H5C 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 H6C 0.9700 . ? C7A C8A 1.4200 . ? C7A C11A 1.4200 . ? C7A H7A 0.9400 . ? C8A C9A 1.4202 . ? C8A H8A 0.9400 . ? C9A C10A 1.4200 . ? C9A H9A 0.9400 . ? C10A C11A 1.4200 . ? C10A H10A 0.9400 . ? C11A H11A 0.9400 . ? C7B C8B 1.4201 . ? C7B C11B 1.4200 . ? C7B H7B 0.9400 . ? C8B C9B 1.4200 . ? C8B H8B 0.9400 . ? C9B C10B 1.4200 . ? C9B H9B 0.9400 . ? C10B C11B 1.4200 . ? C10B H10B 0.9400 . ? C11B H11B 0.9400 . ? Y2 N6 2.2331(9) . ? Y2 N4 2.6218(5) . ? Y2 N4 2.6218(5) 6_565 ? Y2 N5 2.7049(5) . ? Y2 C22A 2.727(2) 6_565 ? Y2 C22A 2.7269 . ? Y2 C18A 2.7391 6_565 ? Y2 C18A 2.7391 . ? Y2 C20B 2.745(2) 6_565 ? Y2 C20B 2.7446(13) . ? Y2 C21B 2.753(2) 6_565 ? Y2 C21B 2.7527(12) . ? N4 C13 1.4580(7) . ? N4 C15 1.4710(9) . ? N4 C12 1.4752(8) . ? N5 C13 1.4633(8) . ? N5 C13 1.4633(8) 6_565 ? N5 C16 1.4666(12) . ? N6 C17 1.4040(10) . ? N6 C14 1.4397(12) . ? C12 N4 1.4752(8) 6_565 ? C12 C14 1.5292(9) . ? C12 H12A 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 H15C 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C16 H16C 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 H17C 0.9700 . ? C18A C19A 1.4202 . ? C18A C22A 1.4198 . ? C18A H18A 0.9400 . ? C19A C20A 1.4196 . ? C19A H19A 0.9400 . ? C20A C21A 1.4200 . ? C20A H20A 0.9400 . ? C21A C22A 1.4202 . ? C21A H21A 0.9400 . ? C22A H22A 0.9400 . ? C18B C19B 1.4202 . ? C18B C22B 1.4198 . ? C18B H18B 0.9400 . ? C19B C20B 1.4197 . ? C19B H19B 0.9400 . ? C20B C21B 1.4200 . ? C20B H20B 0.9400 . ? C21B C22B 1.4201 . ? C21B H21B 0.9400 . ? C22B H22B 0.9400 . ? 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 N3 Y1 N1 69.24(3) . . ? N3 Y1 N1 69.24(3) . 6_565 ? N1 Y1 N1 53.53(2) . 6_565 ? N3 Y1 N2 112.66(3) . . ? N1 Y1 N2 51.703(14) . . ? N1 Y1 N2 51.703(14) 6_565 . ? N3 Y1 C10A 101.49(4) . 6_565 ? N1 Y1 C10A 114.98(3) . 6_565 ? N1 Y1 C10A 166.76(3) 6_565 6_565 ? N2 Y1 C10A 129.02(2) . 6_565 ? N3 Y1 C10A 101.49(3) . . ? N1 Y1 C10A 166.76(2) . . ? N1 Y1 C10A 114.98(2) 6_565 . ? N2 Y1 C10A 129.021(17) . . ? C10A Y1 C10A 75.5 6_565 . ? N3 Y1 C9A 85.02(4) . 6_565 ? N1 Y1 C9A 85.71(5) . 6_565 ? N1 Y1 C9A 136.97(5) 6_565 6_565 ? N2 Y1 C9A 115.95(4) . 6_565 ? C10A Y1 C9A 30.1 6_565 6_565 ? C10A Y1 C9A 103.28(5) . 6_565 ? N3 Y1 C9A 85.021(18) . . ? N1 Y1 C9A 136.97(2) . . ? N1 Y1 C9A 85.71(3) 6_565 . ? N2 Y1 C9A 115.95(2) . . ? C10A Y1 C9A 103.3 6_565 . ? C10A Y1 C9A 30.1 . . ? C9A Y1 C9A 126.97(5) 6_565 . ? N3 Y1 C11A 131.04(3) . . ? N1 Y1 C11A 155.79(2) . . ? N1 Y1 C11A 115.898(18) 6_565 . ? N2 Y1 C11A 104.15(2) . . ? C10A Y1 C11A 77.3 6_565 . ? C10A Y1 C11A 30.0 . . ? C9A Y1 C11A 107.05(5) 6_565 . ? C9A Y1 C11A 49.4 . . ? N3 Y1 C11A 131.04(4) . 6_565 ? N1 Y1 C11A 115.90(2) . 6_565 ? N1 Y1 C11A 155.79(4) 6_565 6_565 ? N2 Y1 C11A 104.15(4) . 6_565 ? C10A Y1 C11A 30.0 6_565 6_565 ? C10A Y1 C11A 77.3 . 6_565 ? C9A Y1 C11A 49.4 6_565 6_565 ? C9A Y1 C11A 107.0 . 6_565 ? C11A Y1 C11A 63.7 . 6_565 ? N3 Y1 C7B 116.958(11) . . ? N1 Y1 C7B 124.66(2) . . ? N1 Y1 C7B 76.464(19) 6_565 . ? N2 Y1 C7B 80.38(2) . . ? C10A Y1 C7B 116.7 6_565 . ? C10A Y1 C7B 50.1 . . ? C9A Y1 C7B 146.45(5) 6_565 . ? C9A Y1 C7B 40.4 . . ? C11A Y1 C7B 39.4 . . ? C11A Y1 C7B 99.7 6_565 . ? N3 Y1 C7B 116.958(11) . 6_565 ? N1 Y1 C7B 76.464(19) . 6_565 ? N1 Y1 C7B 124.66(2) 6_565 6_565 ? N2 Y1 C7B 80.38(2) . 6_565 ? C10A Y1 C7B 50.1 6_565 6_565 ? C10A Y1 C7B 116.7 . 6_565 ? C9A Y1 C7B 40.4 6_565 6_565 ? C9A Y1 C7B 146.4 . 6_565 ? C11A Y1 C7B 99.7 . 6_565 ? C11A Y1 C7B 39.4 6_565 6_565 ? C7B Y1 C7B 126.1 . 6_565 ? C2 N1 C4 110.64(5) . . ? C2 N1 C1 112.84(6) . . ? C4 N1 C1 111.47(4) . . ? C2 N1 Y1 98.61(3) . . ? C4 N1 Y1 132.78(5) . . ? C1 N1 Y1 88.54(5) . . ? C2 N2 C2 106.01(5) . 6_565 ? C2 N2 C5 111.38(5) . . ? C2 N2 C5 111.38(5) 6_565 . ? C2 N2 Y1 95.40(4) . . ? C2 N2 Y1 95.40(4) 6_565 . ? C5 N2 Y1 133.72(6) . . ? C6 N3 C3 111.77(8) . . ? C6 N3 Y1 133.24(8) . . ? C3 N3 Y1 114.99(6) . . ? N1 C1 N1 106.50(5) 6_565 . ? N1 C1 C3 107.49(7) 6_565 . ? N1 C1 C3 107.49(7) . . ? N1 C1 Y1 61.78(4) 6_565 . ? N1 C1 Y1 61.78(4) . . ? C3 C1 Y1 82.37(6) . . ? N1 C1 H1A 111.7 6_565 . ? N1 C1 H1A 111.7 . . ? C3 C1 H1A 111.7 . . ? Y1 C1 H1A 165.9 . . ? N1 C2 N2 105.14(5) . . ? N1 C2 H2A 110.7 . . ? N2 C2 H2A 110.7 . . ? N1 C2 H2B 110.7 . . ? N2 C2 H2B 110.7 . . ? H2A C2 H2B 108.8 . . ? N3 C3 C1 109.36(6) . . ? N3 C3 H3A 109.8 . . ? C1 C3 H3A 109.8 . . ? N3 C3 H3B 109.8 . . ? C1 C3 H3B 109.8 . . ? H3A C3 H3B 108.2 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N2 C5 H5A 109.5 . . ? N2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N3 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8A C7A C11A 108.0 . . ? C8A C7A Y1 74.8 . . ? C11A C7A Y1 74.1 . . ? C8A C7A H7A 126.0 . . ? C11A C7A H7A 126.0 . . ? Y1 C7A H7A 117.1 . . ? C9A C8A C7A 108.0 . . ? C9A C8A Y1 73.8 . . ? C7A C8A Y1 75.6 . . ? C9A C8A H8A 126.0 . . ? C7A C8A H8A 126.0 . . ? Y1 C8A H8A 116.7 . . ? C10A C9A C8A 108.0 . . ? C10A C9A Y1 74.5 . . ? C8A C9A Y1 76.4 . . ? C10A C9A H9A 126.0 . . ? C8A C9A H9A 126.0 . . ? Y1 C9A H9A 115.2 . . ? C11A C10A C9A 108.0 . . ? C11A C10A Y1 76.1 . . ? C9A C10A Y1 75.4 . . ? C11A C10A H10A 126.0 . . ? C9A C10A H10A 126.0 . . ? Y1 C10A H10A 114.7 . . ? C10A C11A C7A 108.0 . . ? C10A C11A Y1 73.9 . . ? C7A C11A Y1 76.3 . . ? C10A C11A H11A 126.0 . . ? C7A C11A H11A 126.0 . . ? Y1 C11A H11A 115.9 . . ? C8B C7B C11B 108.0 . . ? C8B C7B Y1 75.5 . . ? C11B C7B Y1 75.3 . . ? C8B C7B H7B 126.0 . . ? C11B C7B H7B 126.0 . . ? Y1 C7B H7B 115.4 . . ? C9B C8B C7B 108.0 . . ? C9B C8B Y1 75.5 . . ? C7B C8B Y1 74.9 . . ? C9B C8B H8B 126.0 . . ? C7B C8B H8B 126.0 . . ? Y1 C8B H8B 115.7 . . ? C8B C9B C10B 108.0 . . ? C8B C9B Y1 75.0 . . ? C10B C9B Y1 75.1 . . ? C8B C9B H9B 126.0 . . ? C10B C9B H9B 126.0 . . ? Y1 C9B H9B 116.0 . . ? C9B C10B C11B 108.0 . . ? C9B C10B Y1 75.4 . . ? C11B C10B Y1 74.9 . . ? C9B C10B H10B 126.0 . . ? C11B C10B H10B 126.0 . . ? Y1 C10B H10B 115.9 . . ? C10B C11B C7B 108.0 . . ? C10B C11B Y1 75.6 . . ? C7B C11B Y1 75.1 . . ? C10B C11B H11B 126.0 . . ? C7B C11B H11B 126.0 . . ? Y1 C11B H11B 115.5 . . ? N6 Y2 N4 69.741(17) . . ? N6 Y2 N4 69.741(17) . 6_565 ? N4 Y2 N4 53.54(2) . 6_565 ? N6 Y2 N5 113.22(2) . . ? N4 Y2 N5 51.700(17) . . ? N4 Y2 N5 51.700(17) 6_565 . ? N6 Y2 C22A 97.15(3) . 6_565 ? N4 Y2 C22A 162.96(3) . 6_565 ? N4 Y2 C22A 112.48(2) 6_565 6_565 ? N5 Y2 C22A 130.56(3) . 6_565 ? N6 Y2 C22A 97.15(2) . . ? N4 Y2 C22A 112.481(16) . . ? N4 Y2 C22A 162.960(18) 6_565 . ? N5 Y2 C22A 130.556(17) . . ? C22A Y2 C22A 79.1 6_565 . ? N6 Y2 C18A 83.797(15) . 6_565 ? N4 Y2 C18A 134.001(17) . 6_565 ? N4 Y2 C18A 82.554(15) 6_565 6_565 ? N5 Y2 C18A 113.573(8) . 6_565 ? C22A Y2 C18A 30.1 6_565 6_565 ? C22A Y2 C18A 107.5 . 6_565 ? N6 Y2 C18A 83.797(15) . . ? N4 Y2 C18A 82.554(15) . . ? N4 Y2 C18A 134.001(17) 6_565 . ? N5 Y2 C18A 113.573(8) . . ? C22A Y2 C18A 107.5 6_565 . ? C22A Y2 C18A 30.1 . . ? C18A Y2 C18A 132.4 6_565 . ? N6 Y2 C20B 133.20(3) . 6_565 ? N4 Y2 C20B 143.97(5) . 6_565 ? N4 Y2 C20B 103.24(4) 6_565 6_565 ? N5 Y2 C20B 92.57(5) . 6_565 ? C22A Y2 C20B 40.92(6) 6_565 6_565 ? C22A Y2 C20B 93.7 . 6_565 ? C18A Y2 C20B 49.6 6_565 6_565 ? C18A Y2 C20B 122.0 . 6_565 ? N6 Y2 C20B 133.20(2) . . ? N4 Y2 C20B 103.24(3) . . ? N4 Y2 C20B 143.97(3) 6_565 . ? N5 Y2 C20B 92.57(3) . . ? C22A Y2 C20B 93.7 6_565 . ? C22A Y2 C20B 40.9 . . ? C18A Y2 C20B 122.0 6_565 . ? C18A Y2 C20B 49.6 . . ? C20B Y2 C20B 80.1 6_565 . ? N6 Y2 C21B 112.52(5) . 6_565 ? N4 Y2 C21B 173.00(3) . 6_565 ? N4 Y2 C21B 120.38(2) 6_565 6_565 ? N5 Y2 C21B 122.51(5) . 6_565 ? C22A Y2 C21B 15.88(5) 6_565 6_565 ? C22A Y2 C21B 74.1 . 6_565 ? C18A Y2 C21B 41.9 6_565 6_565 ? C18A Y2 C21B 104.2 . 6_565 ? C20B Y2 C21B 29.9 6_565 6_565 ? C20B Y2 C21B 80.2 . 6_565 ? N6 Y2 C21B 112.52(3) . . ? N4 Y2 C21B 120.38(2) . . ? N4 Y2 C21B 173.00(2) 6_565 . ? N5 Y2 C21B 122.51(3) . . ? C22A Y2 C21B 74.1 6_565 . ? C22A Y2 C21B 15.9 . . ? C18A Y2 C21B 104.2 6_565 . ? C18A Y2 C21B 41.9 . . ? C20B Y2 C21B 80.2 6_565 . ? C20B Y2 C21B 29.9 . . ? C21B Y2 C21B 65.4 6_565 . ? C13 N4 C15 110.31(4) . . ? C13 N4 C12 113.47(4) . . ? C15 N4 C12 111.87(6) . . ? C13 N4 Y2 98.70(3) . . ? C15 N4 Y2 132.66(3) . . ? C12 N4 Y2 88.01(3) . . ? C13 N5 C13 106.08(7) . 6_565 ? C13 N5 C16 111.40(4) . . ? C13 N5 C16 111.40(4) 6_565 . ? C13 N5 Y2 95.07(3) . . ? C13 N5 Y2 95.07(3) 6_565 . ? C16 N5 Y2 134.20(6) . . ? C17 N6 C14 111.97(9) . . ? C17 N6 Y2 132.82(7) . . ? C14 N6 Y2 115.20(4) . . ? N4 C12 N4 106.37(7) . 6_565 ? N4 C12 C14 107.65(3) . . ? N4 C12 C14 107.65(3) 6_565 . ? N4 C12 Y2 62.15(3) . . ? N4 C12 Y2 62.15(3) 6_565 . ? C14 C12 Y2 81.61(5) . . ? N4 C12 H12A 111.6 . . ? N4 C12 H12A 111.6 6_565 . ? C14 C12 H12A 111.6 . . ? Y2 C12 H12A 166.8 . . ? N4 C13 N5 105.40(4) . . ? N4 C13 H13A 110.7 . . ? N5 C13 H13A 110.7 . . ? N4 C13 H13B 110.7 . . ? N5 C13 H13B 110.7 . . ? H13A C13 H13B 108.8 . . ? N6 C14 C12 109.69(8) . . ? N6 C14 H14A 109.7 . . ? C12 C14 H14A 109.7 . . ? N6 C14 H14B 109.7 . . ? C12 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? N4 C15 H15A 109.5 . . ? N4 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N4 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N5 C16 H16A 109.5 . . ? N5 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N5 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N6 C17 H17A 109.5 . . ? N6 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N6 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19A C18A C22A 108.0 . . ? C19A C18A Y2 77.5 . . ? C22A C18A Y2 74.5 . . ? C19A C18A H18A 126.0 . . ? C22A C18A H18A 126.0 . . ? Y2 C18A H18A 114.3 . . ? C20A C19A C18A 108.0 . . ? C20A C19A Y2 76.4 . . ? C18A C19A Y2 72.8 . . ? C20A C19A H19A 126.0 . . ? C18A C19A H19A 126.0 . . ? Y2 C19A H19A 116.9 . . ? C19A C20A C21A 108.0 . . ? C19A C20A Y2 74.4 . . ? C21A C20A Y2 73.6 . . ? C19A C20A H20A 126.0 . . ? C21A C20A H20A 126.0 . . ? Y2 C20A H20A 118.0 . . ? C22A C21A C20A 108.0 . . ? C22A C21A Y2 73.0 . . ? C20A C21A Y2 77.1 . . ? C22A C21A H21A 126.0 . . ? C20A C21A H21A 126.0 . . ? Y2 C21A H21A 116.1 . . ? C21A C22A C18A 108.0 . . ? C21A C22A Y2 77.2 . . ? C18A C22A Y2 75.4 . . ? C21A C22A H22A 126.0 . . ? C18A C22A H22A 126.0 . . ? Y2 C22A H22A 113.8 . . ? C19B C18B C22B 108.0 . . ? C19B C18B Y2 74.5 . . ? C22B C18B Y2 75.0 . . ? C19B C18B H18B 126.0 . . ? C22B C18B H18B 126.0 . . ? Y2 C18B H18B 116.6 . . ? C20B C19B C18B 108.0 . . ? C20B C19B Y2 74.5 . . ? C18B C19B Y2 75.8 . . ? C20B C19B H19B 126.0 . . ? C18B C19B H19B 126.0 . . ? Y2 C19B H19B 115.9 . . ? C19B C20B C21B 108.0 . . ? C19B C20B Y2 75.6 . . ? C21B C20B Y2 75.3 . . ? C19B C20B H20B 126.0 . . ? C21B C20B H20B 126.0 . . ? Y2 C20B H20B 115.2 . . ? C20B C21B C22B 108.0 . . ? C20B C21B Y2 74.7 . . ? C22B C21B Y2 75.9 . . ? C20B C21B H21B 126.0 . . ? C22B C21B H21B 126.0 . . ? Y2 C21B H21B 115.6 . . ? C21B C22B C18B 108.0 . . ? C21B C22B Y2 74.3 . . ? C18B C22B Y2 75.3 . . ? C21B C22B H22B 126.0 . . ? C18B C22B H22B 126.0 . . ? Y2 C22B H22B 116.4 . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 72.19 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 1.072 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.046 _vrf_CHEMW03_compound4 ; PROBLEM: ALERT: The ratio of given/expected molecular weight as RESPONSE: Highly disordered toluene was squeezed. ; _vrf_PLAT043_compound4 ; PROBLEM: Check Reported Molecular Weight ................ 436.43 RESPONSE: Highly disordered toluene was squeezed. ; _vrf_PLAT044_compound4 ; PROBLEM: Calculated and Reported Dx Differ .............. ? RESPONSE: Highly disordered toluene was squeezed. ; #============================================================================== #============================================================================== data_compound5 _database_code_depnum_ccdc_archive 'CCDC 783496' #TrackingRef 'compound5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H44 Ga2 N2' _chemical_formula_sum 'C20 H44 Ga2 N2' _chemical_formula_weight 452.01 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 8.90800(10) _cell_length_b 12.3329(2) _cell_length_c 11.6776(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.7611(9) _cell_angle_gamma 90.00 _cell_volume 1214.75(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 24457 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 2.222 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5553 _exptl_absorpt_correction_T_max 0.6649 _exptl_absorpt_process_details 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(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_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37072 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_av_sigmaI/netI 0.0143 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3544 _reflns_number_gt 3250 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect, Bruker AXS, 2004' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-PLUS (1990)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0363P)^2^+0.7315P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3544 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0281 _refine_ls_R_factor_gt 0.0253 _refine_ls_wR_factor_ref 0.0680 _refine_ls_wR_factor_gt 0.0661 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 Ga1 Ga 0.347013(16) 0.545423(12) 0.353481(12) 0.01744(6) Uani 1 1 d . . . N1 N 0.35958(14) 0.39955(9) 0.43733(11) 0.0210(2) Uani 1 1 d . . . C1 C 0.15019(16) 0.62167(11) 0.36121(13) 0.0218(3) Uani 1 1 d . . . C2 C 0.14683(19) 0.61806(15) 0.49097(15) 0.0312(3) Uani 1 1 d . . . H2A H 0.0553 0.6592 0.4965 0.047 Uiso 1 1 calc R . . H2B H 0.2445 0.6501 0.5452 0.047 Uiso 1 1 calc R . . H2C H 0.1385 0.5426 0.5145 0.047 Uiso 1 1 calc R . . C3 C -0.00541(18) 0.57478(15) 0.27711(16) 0.0319(3) Uani 1 1 d . . . H3A H -0.0152 0.4989 0.2986 0.048 Uiso 1 1 calc R . . H3B H -0.0058 0.5789 0.1932 0.048 Uiso 1 1 calc R . . H3C H -0.0948 0.6165 0.2857 0.048 Uiso 1 1 calc R . . C4 C 0.1624(2) 0.74088(13) 0.32776(17) 0.0319(3) Uani 1 1 d . . . H4A H 0.1602 0.7457 0.2435 0.048 Uiso 1 1 calc R . . H4B H 0.2619 0.7716 0.3808 0.048 Uiso 1 1 calc R . . H4C H 0.0728 0.7815 0.3376 0.048 Uiso 1 1 calc R . . C5 C 0.38651(19) 0.51988(13) 0.19479(13) 0.0251(3) Uani 1 1 d . . . C6 C 0.2374(3) 0.4963(2) 0.09001(17) 0.0522(6) Uani 1 1 d . . . H6A H 0.2635 0.4925 0.0148 0.078 Uiso 1 1 calc R . . H6B H 0.1599 0.5543 0.0838 0.078 Uiso 1 1 calc R . . H6C H 0.1923 0.4270 0.1038 0.078 Uiso 1 1 calc R . . C7 C 0.4612(3) 0.62494(15) 0.16403(17) 0.0404(4) Uani 1 1 d . . . H7A H 0.5619 0.6395 0.2277 0.061 Uiso 1 1 calc R . . H7B H 0.3886 0.6859 0.1585 0.061 Uiso 1 1 calc R . . H7C H 0.4802 0.6159 0.0865 0.061 Uiso 1 1 calc R . . C8 C 0.5087(3) 0.43110(17) 0.20647(17) 0.0404(4) Uani 1 1 d . . . H8A H 0.4684 0.3627 0.2278 0.061 Uiso 1 1 calc R . . H8B H 0.6074 0.4507 0.2698 0.061 Uiso 1 1 calc R . . H8C H 0.5291 0.4227 0.1293 0.061 Uiso 1 1 calc R . . C9 C 0.46471(16) 0.37243(11) 0.53561(13) 0.0218(3) Uani 1 1 d . . . H9 H 0.4531 0.3009 0.5619 0.026 Uiso 1 1 calc R . . C10 C 0.23473(19) 0.32176(13) 0.37512(15) 0.0301(3) Uani 1 1 d . . . H10A H 0.2568 0.2515 0.4164 0.045 Uiso 1 1 calc R . . H10B H 0.2325 0.3132 0.2911 0.045 Uiso 1 1 calc R . . H10C H 0.1318 0.3487 0.3764 0.045 Uiso 1 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 Ga1 0.01734(8) 0.01885(9) 0.01491(8) -0.00018(5) 0.00350(6) 0.00008(5) N1 0.0207(5) 0.0188(5) 0.0237(5) -0.0026(4) 0.0075(4) -0.0025(4) C1 0.0190(6) 0.0228(6) 0.0226(6) 0.0007(5) 0.0051(5) 0.0020(5) C2 0.0284(7) 0.0399(9) 0.0278(7) 0.0000(6) 0.0126(6) 0.0045(6) C3 0.0201(6) 0.0369(8) 0.0341(8) -0.0008(7) 0.0023(6) 0.0013(6) C4 0.0282(7) 0.0257(7) 0.0412(9) 0.0061(6) 0.0107(6) 0.0069(6) C5 0.0292(7) 0.0283(7) 0.0174(6) -0.0007(5) 0.0067(5) 0.0036(6) C6 0.0412(10) 0.0881(17) 0.0236(8) -0.0089(10) 0.0054(7) -0.0112(11) C7 0.0620(12) 0.0342(9) 0.0324(8) 0.0035(7) 0.0256(8) -0.0006(8) C8 0.0560(11) 0.0415(9) 0.0293(8) 0.0042(7) 0.0216(8) 0.0187(9) C9 0.0225(6) 0.0196(6) 0.0252(6) -0.0027(5) 0.0101(5) -0.0036(5) C10 0.0256(7) 0.0260(7) 0.0330(8) -0.0029(6) 0.0016(6) -0.0071(6) _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 Ga1 C1 2.0170(14) . ? Ga1 C5 2.0191(14) . ? Ga1 C9 2.0296(14) 3_666 ? Ga1 N1 2.0340(12) . ? N1 C9 1.2707(19) . ? N1 C10 1.4715(18) . ? C1 C2 1.526(2) . ? C1 C3 1.531(2) . ? C1 C4 1.534(2) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.517(2) . ? C5 C8 1.519(2) . ? C5 C7 1.550(2) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 Ga1 2.0296(14) 3_666 ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? 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 C1 Ga1 C5 121.63(6) . . ? C1 Ga1 C9 106.89(6) . 3_666 ? C5 Ga1 C9 108.14(6) . 3_666 ? C1 Ga1 N1 107.75(5) . . ? C5 Ga1 N1 107.76(6) . . ? C9 Ga1 N1 103.18(5) 3_666 . ? C9 N1 C10 119.65(12) . . ? C9 N1 Ga1 125.31(10) . . ? C10 N1 Ga1 115.04(10) . . ? C2 C1 C3 108.85(13) . . ? C2 C1 C4 107.85(13) . . ? C3 C1 C4 108.80(13) . . ? C2 C1 Ga1 109.01(10) . . ? C3 C1 Ga1 114.57(10) . . ? C4 C1 Ga1 107.56(10) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 C8 110.55(17) . . ? C6 C5 C7 107.63(16) . . ? C8 C5 C7 105.95(15) . . ? C6 C5 Ga1 113.84(12) . . ? C8 C5 Ga1 111.19(10) . . ? C7 C5 Ga1 107.26(11) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 Ga1 131.50(11) . 3_666 ? N1 C9 H9 114.2 . . ? Ga1 C9 H9 114.2 3_666 . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.818 _refine_diff_density_min -0.481 _refine_diff_density_rms 0.066