# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_email R.E.MULVEY@STRATH.AC.UK _publ_section_title ; After-effects of Lithium-mediated Alumination of 3-iodoanisole: Isolation of Molecular Salt Elimination and Trapped-benzyne Products ; loop_ _publ_author_name R.E.Mulvey A.R.Kennedy S.Robertson E.Crosbie _publ_contact_author_name 'Alan Kennedy' #===END #----------------------------------------------- #---------------COMPOUND 7---------------------- #----------------------------------------------- data_srec1103 _database_code_depnum_ccdc_archive 'CCDC 815746' #TrackingRef '- Combined.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H20 O2' _chemical_formula_sum 'C27 H20 O2' _chemical_formula_weight 376.43 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' O O 0.0106 0.0060 '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' 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 10.7897(3) _cell_length_b 17.0361(4) _cell_length_c 11.4052(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.652(3) _cell_angle_gamma 90.00 _cell_volume 1961.72(9) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4257 _cell_measurement_theta_min 3.1226 _cell_measurement_theta_max 29.4612 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_T_min 0.97300 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Xcalibur, Eos' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9138 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0432 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 29.53 _reflns_number_total 4795 _reflns_number_gt 3789 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0397P)^2^+0.5957P] 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 4795 _refine_ls_number_parameters 342 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1044 _refine_ls_wR_factor_gt 0.0961 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.000 _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 C1 C 0.40735(15) 0.12172(10) 0.26133(13) 0.0254(3) Uani 1 1 d . . . H1A H 0.3770(15) 0.0639(11) 0.2499(15) 0.032(4) Uiso 1 1 d . . . H1B H 0.4430(16) 0.1383(10) 0.1923(16) 0.033(4) Uiso 1 1 d . . . H1C H 0.3304(17) 0.1557(11) 0.2625(16) 0.036(5) Uiso 1 1 d . . . O1 O 0.51706(9) 0.12970(6) 0.37689(8) 0.0232(2) Uani 1 1 d . . . C2 C 0.49497(12) 0.11192(8) 0.48371(12) 0.0173(3) Uani 1 1 d . . . C3 C 0.37799(13) 0.07826(8) 0.48874(13) 0.0198(3) Uani 1 1 d . . . H3 H 0.3047(16) 0.0668(9) 0.4094(15) 0.028(4) Uiso 1 1 d . . . C4 C 0.36783(13) 0.05865(8) 0.60267(13) 0.0209(3) Uani 1 1 d . . . H4 H 0.2832(15) 0.0340(9) 0.6031(14) 0.025(4) Uiso 1 1 d . . . C5 C 0.47187(13) 0.07094(8) 0.71601(13) 0.0185(3) Uani 1 1 d . . . H5 H 0.4664(14) 0.0568(9) 0.7971(14) 0.022(4) Uiso 1 1 d . . . C6 C 0.58462(12) 0.10591(8) 0.70964(12) 0.0169(3) Uani 1 1 d . . . C7 C 0.59590(12) 0.12784(8) 0.59667(12) 0.0167(3) Uani 1 1 d . . . C8 C 0.73558(12) 0.16318(8) 0.62974(12) 0.0176(3) Uani 1 1 d . . . C9 C 0.82927(12) 0.09245(8) 0.67192(12) 0.0185(3) Uani 1 1 d . . . C10 C 0.90637(13) 0.05055(9) 0.61954(13) 0.0228(3) Uani 1 1 d . . . H10 H 0.9134(14) 0.0676(9) 0.5358(14) 0.021(4) Uiso 1 1 d . . . C11 C 0.97371(14) -0.01581(10) 0.68388(14) 0.0272(3) Uani 1 1 d . . . H11 H 1.0304(17) -0.0433(11) 0.6496(16) 0.040(5) Uiso 1 1 d . . . C12 C 0.96215(14) -0.03973(9) 0.79554(14) 0.0258(3) Uani 1 1 d . . . H12 H 1.0083(16) -0.0866(10) 0.8389(16) 0.032(4) Uiso 1 1 d . . . C13 C 0.88218(13) 0.00225(9) 0.84734(13) 0.0210(3) Uani 1 1 d . . . H13 H 0.8733(14) -0.0149(9) 0.9251(14) 0.021(4) Uiso 1 1 d . . . C14 C 0.81801(12) 0.06816(8) 0.78507(12) 0.0177(3) Uani 1 1 d . . . C15 C 0.72019(12) 0.12595(8) 0.80951(12) 0.0171(3) Uani 1 1 d . . . C16 C 0.75461(13) 0.22673(8) 0.54673(12) 0.0188(3) Uani 1 1 d . . . C17 C 0.65158(14) 0.27942(9) 0.49307(13) 0.0230(3) Uani 1 1 d . . . H17 H 0.5689(15) 0.2732(9) 0.5094(14) 0.025(4) Uiso 1 1 d . . . C18 C 0.66503(15) 0.34049(9) 0.41846(14) 0.0268(3) Uani 1 1 d . . . H18 H 0.5927(17) 0.3785(11) 0.3803(16) 0.038(5) Uiso 1 1 d . . . C19 C 0.78283(15) 0.34921(9) 0.39601(14) 0.0269(3) Uani 1 1 d . . . H19 H 0.7904(16) 0.3899(10) 0.3412(16) 0.032(4) Uiso 1 1 d . . . C20 C 0.88656(14) 0.29781(9) 0.44987(13) 0.0263(3) Uani 1 1 d . . . H20 H 0.9682(16) 0.3036(10) 0.4360(14) 0.029(4) Uiso 1 1 d . . . C21 C 0.87331(13) 0.23686(9) 0.52583(13) 0.0226(3) Uani 1 1 d . . . H21 H 0.9479(16) 0.2003(10) 0.5657(15) 0.029(4) Uiso 1 1 d . . . C22 C 0.72678(12) 0.13909(8) 0.94155(12) 0.0180(3) Uani 1 1 d . . . C23 C 0.69333(13) 0.07891(9) 1.00806(13) 0.0199(3) Uani 1 1 d . . . H23 H 0.6682(14) 0.0269(10) 0.9685(14) 0.023(4) Uiso 1 1 d . . . C24 C 0.69417(13) 0.09223(9) 1.12854(13) 0.0228(3) Uani 1 1 d . . . H24 H 0.6712(15) 0.0505(10) 1.1732(15) 0.028(4) Uiso 1 1 d . . . C25 C 0.72970(14) 0.16502(10) 1.18446(13) 0.0271(3) Uani 1 1 d . . . H25 H 0.7294(16) 0.1745(10) 1.2685(16) 0.034(5) Uiso 1 1 d . . . C26 C 0.76621(16) 0.22425(10) 1.12011(14) 0.0293(3) Uani 1 1 d . . . H26 H 0.7908(18) 0.2751(11) 1.1553(17) 0.043(5) Uiso 1 1 d . . . C27 C 0.76403(14) 0.21171(9) 0.99879(13) 0.0236(3) Uani 1 1 d . . . H27 H 0.7865(15) 0.2539(10) 0.9515(15) 0.029(4) Uiso 1 1 d . . . O2 O 0.75179(9) 0.19599(6) 0.75361(8) 0.0181(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 0.0280(7) 0.0271(8) 0.0164(7) 0.0007(6) 0.0020(6) 0.0015(6) O1 0.0240(5) 0.0279(5) 0.0159(5) 0.0010(4) 0.0049(4) -0.0036(4) C2 0.0195(6) 0.0150(6) 0.0170(6) 0.0003(5) 0.0060(5) 0.0009(5) C3 0.0167(6) 0.0185(7) 0.0210(7) -0.0010(5) 0.0027(5) -0.0003(5) C4 0.0164(6) 0.0204(7) 0.0267(7) -0.0012(6) 0.0088(5) -0.0016(5) C5 0.0190(6) 0.0176(7) 0.0209(7) 0.0009(5) 0.0096(5) 0.0006(5) C6 0.0178(6) 0.0149(6) 0.0174(6) -0.0010(5) 0.0054(5) 0.0009(5) C7 0.0160(6) 0.0159(6) 0.0189(6) -0.0002(5) 0.0069(5) -0.0009(5) C8 0.0180(6) 0.0210(7) 0.0147(6) -0.0030(5) 0.0068(5) -0.0029(5) C9 0.0138(6) 0.0229(7) 0.0171(6) -0.0021(5) 0.0034(5) -0.0044(5) C10 0.0186(6) 0.0320(8) 0.0186(6) -0.0032(6) 0.0075(5) -0.0021(6) C11 0.0205(7) 0.0346(9) 0.0268(8) -0.0037(7) 0.0088(6) 0.0047(6) C12 0.0188(7) 0.0301(8) 0.0251(7) 0.0000(6) 0.0037(6) 0.0047(6) C13 0.0167(6) 0.0257(7) 0.0184(6) -0.0004(6) 0.0037(5) -0.0020(5) C14 0.0123(6) 0.0232(7) 0.0169(6) -0.0032(5) 0.0043(5) -0.0040(5) C15 0.0172(6) 0.0174(6) 0.0174(6) 0.0004(5) 0.0068(5) -0.0027(5) C16 0.0206(6) 0.0212(7) 0.0144(6) -0.0036(5) 0.0058(5) -0.0068(5) C17 0.0240(7) 0.0230(7) 0.0241(7) -0.0007(6) 0.0111(6) -0.0049(6) C18 0.0312(8) 0.0224(7) 0.0271(7) 0.0012(6) 0.0107(6) -0.0022(6) C19 0.0353(8) 0.0252(8) 0.0230(7) 0.0004(6) 0.0136(6) -0.0093(6) C20 0.0255(7) 0.0330(8) 0.0235(7) -0.0035(6) 0.0127(6) -0.0112(6) C21 0.0207(7) 0.0268(8) 0.0202(7) -0.0022(6) 0.0071(5) -0.0050(6) C22 0.0152(6) 0.0224(7) 0.0167(6) -0.0007(5) 0.0058(5) -0.0004(5) C23 0.0189(6) 0.0208(7) 0.0201(6) -0.0008(5) 0.0069(5) -0.0002(5) C24 0.0223(7) 0.0277(8) 0.0197(7) 0.0043(6) 0.0090(5) -0.0006(6) C25 0.0299(8) 0.0354(9) 0.0174(7) -0.0027(6) 0.0101(6) -0.0029(6) C26 0.0392(9) 0.0271(8) 0.0223(7) -0.0071(6) 0.0118(6) -0.0088(7) C27 0.0276(7) 0.0233(7) 0.0205(7) -0.0012(6) 0.0092(6) -0.0061(6) O2 0.0218(5) 0.0194(5) 0.0149(4) -0.0016(4) 0.0086(4) -0.0053(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 C1 O1 1.4339(16) . ? C1 H1A 1.032(18) . ? C1 H1B 1.030(18) . ? C1 H1C 1.016(18) . ? O1 C2 1.3557(16) . ? C2 C7 1.3890(17) . ? C2 C3 1.4058(19) . ? C3 C4 1.383(2) . ? C3 H3 0.989(16) . ? C4 C5 1.3969(19) . ? C4 H4 1.007(16) . ? C5 C6 1.3792(18) . ? C5 H5 0.977(15) . ? C6 C7 1.3875(18) . ? C6 C15 1.5422(17) . ? C7 C8 1.5411(17) . ? C8 O2 1.4712(15) . ? C8 C16 1.4992(19) . ? C8 C9 1.5369(19) . ? C9 C10 1.3818(19) . ? C9 C14 1.4007(19) . ? C10 C11 1.403(2) . ? C10 H10 1.027(15) . ? C11 C12 1.384(2) . ? C11 H11 0.956(19) . ? C12 C13 1.402(2) . ? C12 H12 0.978(17) . ? C13 C14 1.3775(19) . ? C13 H13 0.970(15) . ? C14 C15 1.5390(19) . ? C15 O2 1.4492(16) . ? C15 C22 1.4992(18) . ? C16 C17 1.392(2) . ? C16 C21 1.3937(19) . ? C17 C18 1.384(2) . ? C17 H17 0.979(16) . ? C18 C19 1.390(2) . ? C18 H18 0.989(18) . ? C19 C20 1.383(2) . ? C19 H19 0.957(18) . ? C20 C21 1.392(2) . ? C20 H20 0.954(16) . ? C21 H21 0.993(16) . ? C22 C27 1.3904(19) . ? C22 C23 1.396(2) . ? C23 C24 1.390(2) . ? C23 H23 0.988(16) . ? C24 C25 1.385(2) . ? C24 H24 0.956(17) . ? C25 C26 1.384(2) . ? C25 H25 0.973(17) . ? C26 C27 1.392(2) . ? C26 H26 0.952(19) . ? C27 H27 0.979(17) . ? 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 O1 C1 H1A 109.2(9) . . ? O1 C1 H1B 105.5(9) . . ? H1A C1 H1B 110.6(13) . . ? O1 C1 H1C 110.3(10) . . ? H1A C1 H1C 108.7(13) . . ? H1B C1 H1C 112.5(14) . . ? C2 O1 C1 117.06(11) . . ? O1 C2 C7 117.45(12) . . ? O1 C2 C3 124.95(12) . . ? C7 C2 C3 117.60(12) . . ? C4 C3 C2 120.44(12) . . ? C4 C3 H3 120.6(9) . . ? C2 C3 H3 118.9(9) . . ? C3 C4 C5 121.94(13) . . ? C3 C4 H4 118.6(9) . . ? C5 C4 H4 119.5(9) . . ? C6 C5 C4 116.87(13) . . ? C6 C5 H5 120.4(9) . . ? C4 C5 H5 122.8(9) . . ? C5 C6 C7 122.21(12) . . ? C5 C6 C15 132.94(12) . . ? C7 C6 C15 104.79(11) . . ? C6 C7 C2 120.79(12) . . ? C6 C7 C8 106.04(10) . . ? C2 C7 C8 133.03(12) . . ? O2 C8 C16 109.61(11) . . ? O2 C8 C9 98.92(9) . . ? C16 C8 C9 122.84(11) . . ? O2 C8 C7 99.11(10) . . ? C16 C8 C7 117.87(11) . . ? C9 C8 C7 104.40(11) . . ? C10 C9 C14 120.44(13) . . ? C10 C9 C8 134.39(13) . . ? C14 C9 C8 105.01(11) . . ? C9 C10 C11 118.03(14) . . ? C9 C10 H10 120.6(9) . . ? C11 C10 H10 121.3(9) . . ? C12 C11 C10 121.36(14) . . ? C12 C11 H11 120.7(11) . . ? C10 C11 H11 117.9(11) . . ? C11 C12 C13 120.42(14) . . ? C11 C12 H12 120.7(10) . . ? C13 C12 H12 118.8(10) . . ? C14 C13 C12 118.08(13) . . ? C14 C13 H13 121.6(9) . . ? C12 C13 H13 120.3(9) . . ? C13 C14 C9 121.66(13) . . ? C13 C14 C15 132.85(12) . . ? C9 C14 C15 105.40(11) . . ? O2 C15 C22 112.57(11) . . ? O2 C15 C14 99.46(10) . . ? C22 C15 C14 119.01(11) . . ? O2 C15 C6 99.58(9) . . ? C22 C15 C6 118.13(11) . . ? C14 C15 C6 104.90(10) . . ? C17 C16 C21 118.99(13) . . ? C17 C16 C8 118.52(12) . . ? C21 C16 C8 122.43(12) . . ? C18 C17 C16 120.98(13) . . ? C18 C17 H17 119.9(9) . . ? C16 C17 H17 119.1(9) . . ? C17 C18 C19 119.64(14) . . ? C17 C18 H18 121.7(10) . . ? C19 C18 H18 118.7(10) . . ? C20 C19 C18 119.99(14) . . ? C20 C19 H19 120.5(10) . . ? C18 C19 H19 119.5(10) . . ? C19 C20 C21 120.29(14) . . ? C19 C20 H20 120.7(10) . . ? C21 C20 H20 119.0(10) . . ? C20 C21 C16 120.09(14) . . ? C20 C21 H21 120.6(9) . . ? C16 C21 H21 119.3(9) . . ? C27 C22 C23 119.04(13) . . ? C27 C22 C15 120.53(12) . . ? C23 C22 C15 120.41(12) . . ? C24 C23 C22 120.30(13) . . ? C24 C23 H23 120.2(9) . . ? C22 C23 H23 119.5(9) . . ? C25 C24 C23 120.38(14) . . ? C25 C24 H24 120.1(10) . . ? C23 C24 H24 119.5(10) . . ? C26 C25 C24 119.52(14) . . ? C26 C25 H25 120.1(11) . . ? C24 C25 H25 120.3(11) . . ? C25 C26 C27 120.46(14) . . ? C25 C26 H26 121.9(11) . . ? C27 C26 H26 117.6(11) . . ? C22 C27 C26 120.27(14) . . ? C22 C27 H27 118.8(10) . . ? C26 C27 H27 121.0(10) . . ? C15 O2 C8 98.21(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 O1 C2 C7 -172.91(12) . . . . ? C1 O1 C2 C3 7.42(19) . . . . ? O1 C2 C3 C4 176.69(13) . . . . ? C7 C2 C3 C4 -3.0(2) . . . . ? C2 C3 C4 C5 -0.3(2) . . . . ? C3 C4 C5 C6 1.9(2) . . . . ? C4 C5 C6 C7 -0.3(2) . . . . ? C4 C5 C6 C15 -176.89(13) . . . . ? C5 C6 C7 C2 -3.0(2) . . . . ? C15 C6 C7 C2 174.41(12) . . . . ? C5 C6 C7 C8 -179.26(12) . . . . ? C15 C6 C7 C8 -1.83(14) . . . . ? O1 C2 C7 C6 -175.13(12) . . . . ? C3 C2 C7 C6 4.56(19) . . . . ? O1 C2 C7 C8 -0.1(2) . . . . ? C3 C2 C7 C8 179.62(14) . . . . ? C6 C7 C8 O2 -30.99(13) . . . . ? C2 C7 C8 O2 153.42(14) . . . . ? C6 C7 C8 C16 -148.98(12) . . . . ? C2 C7 C8 C16 35.4(2) . . . . ? C6 C7 C8 C9 70.74(13) . . . . ? C2 C7 C8 C9 -104.85(16) . . . . ? O2 C8 C9 C10 -150.97(14) . . . . ? C16 C8 C9 C10 -30.6(2) . . . . ? C7 C8 C9 C10 107.16(16) . . . . ? O2 C8 C9 C14 33.80(12) . . . . ? C16 C8 C9 C14 154.18(12) . . . . ? C7 C8 C9 C14 -68.07(12) . . . . ? C14 C9 C10 C11 -0.9(2) . . . . ? C8 C9 C10 C11 -175.53(14) . . . . ? C9 C10 C11 C12 1.0(2) . . . . ? C10 C11 C12 C13 0.0(2) . . . . ? C11 C12 C13 C14 -1.1(2) . . . . ? C12 C13 C14 C9 1.21(19) . . . . ? C12 C13 C14 C15 177.26(13) . . . . ? C10 C9 C14 C13 -0.24(19) . . . . ? C8 C9 C14 C13 175.81(12) . . . . ? C10 C9 C14 C15 -177.23(12) . . . . ? C8 C9 C14 C15 -1.18(13) . . . . ? C13 C14 C15 O2 151.06(14) . . . . ? C9 C14 C15 O2 -32.44(12) . . . . ? C13 C14 C15 C22 28.6(2) . . . . ? C9 C14 C15 C22 -154.93(11) . . . . ? C13 C14 C15 C6 -106.30(16) . . . . ? C9 C14 C15 C6 70.21(12) . . . . ? C5 C6 C15 O2 -148.30(14) . . . . ? C7 C6 C15 O2 34.68(13) . . . . ? C5 C6 C15 C22 -26.2(2) . . . . ? C7 C6 C15 C22 156.79(12) . . . . ? C5 C6 C15 C14 109.15(16) . . . . ? C7 C6 C15 C14 -67.87(13) . . . . ? O2 C8 C16 C17 -77.65(14) . . . . ? C9 C8 C16 C17 167.15(12) . . . . ? C7 C8 C16 C17 34.60(18) . . . . ? O2 C8 C16 C21 99.56(14) . . . . ? C9 C8 C16 C21 -15.65(19) . . . . ? C7 C8 C16 C21 -148.20(13) . . . . ? C21 C16 C17 C18 0.9(2) . . . . ? C8 C16 C17 C18 178.22(13) . . . . ? C16 C17 C18 C19 0.4(2) . . . . ? C17 C18 C19 C20 -1.1(2) . . . . ? C18 C19 C20 C21 0.5(2) . . . . ? C19 C20 C21 C16 0.8(2) . . . . ? C17 C16 C21 C20 -1.5(2) . . . . ? C8 C16 C21 C20 -178.71(13) . . . . ? O2 C15 C22 C27 -1.85(17) . . . . ? C14 C15 C22 C27 113.86(15) . . . . ? C6 C15 C22 C27 -117.10(14) . . . . ? O2 C15 C22 C23 177.04(11) . . . . ? C14 C15 C22 C23 -67.25(16) . . . . ? C6 C15 C22 C23 61.79(17) . . . . ? C27 C22 C23 C24 1.6(2) . . . . ? C15 C22 C23 C24 -177.30(12) . . . . ? C22 C23 C24 C25 -0.8(2) . . . . ? C23 C24 C25 C26 -0.9(2) . . . . ? C24 C25 C26 C27 1.7(2) . . . . ? C23 C22 C27 C26 -0.8(2) . . . . ? C15 C22 C27 C26 178.11(13) . . . . ? C25 C26 C27 C22 -0.9(2) . . . . ? C22 C15 O2 C8 -179.72(10) . . . . ? C14 C15 O2 C8 53.29(10) . . . . ? C6 C15 O2 C8 -53.71(11) . . . . ? C16 C8 O2 C15 176.30(10) . . . . ? C9 C8 O2 C15 -54.01(10) . . . . ? C7 C8 O2 C15 52.26(10) . . . . ? _diffrn_measured_fraction_theta_max 0.876 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.327 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.044 # Attachment '- Combined.CIF' #----------------------------------------------- #---------------COMPOUND 5---------------------- #----------------------------------------------- data_srec1101 _database_code_depnum_ccdc_archive 'CCDC 847968' #TrackingRef '- Combined.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H76 I4 Li4 N4' _chemical_formula_sum 'C36 H76 I4 Li4 N4' _chemical_formula_weight 1100.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/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 25.5194(9) _cell_length_b 10.7301(2) _cell_length_c 19.8807(6) _cell_angle_alpha 90.00 _cell_angle_beta 118.682(4) _cell_angle_gamma 90.00 _cell_volume 4775.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 4989 _cell_measurement_theta_min 2.7956 _cell_measurement_theta_max 29.6742 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2176 _exptl_absorpt_coefficient_mu 2.636 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.68803 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Xcalibur, Sapphire3, Gemini' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11422 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0592 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 28.99 _reflns_number_total 5807 _reflns_number_gt 4687 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0227P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5807 _refine_ls_number_parameters 233 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0582 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.0794 _refine_ls_wR_factor_gt 0.0730 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.000 _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 Li1 Li 0.0499(3) 0.1371(7) 0.2108(4) 0.0274(16) Uani 1 1 d . . . Li2 Li 0.0648(3) 0.3802(6) 0.3466(4) 0.0263(16) Uani 1 1 d . . . I1 I 0.076750(12) 0.11777(2) 0.368587(14) 0.02302(8) Uani 1 1 d . . . I2 I 0.058027(12) 0.40640(2) 0.202558(15) 0.02416(8) Uani 1 1 d . . . N1 N 0.11028(14) 0.0087(3) 0.20499(17) 0.0190(7) Uani 1 1 d D . . N2 N 0.13537(15) 0.4438(3) 0.45031(18) 0.0202(7) Uani 1 1 d D . . C1 C 0.08591(19) -0.1192(3) 0.1751(2) 0.0229(9) Uani 1 1 d . . . C2 C 0.13539(19) -0.2089(4) 0.1826(2) 0.0271(10) Uani 1 1 d . . . H2A H 0.1621 -0.2266 0.2375 0.033 Uiso 1 1 calc R . . H2B H 0.1171 -0.2885 0.1570 0.033 Uiso 1 1 calc R . . C3 C 0.17213(19) -0.1566(4) 0.1475(2) 0.0287(10) Uani 1 1 d . . . H3A H 0.1462 -0.1416 0.0920 0.034 Uiso 1 1 calc R . . H3B H 0.2036 -0.2167 0.1538 0.034 Uiso 1 1 calc R . . C4 C 0.20042(19) -0.0348(4) 0.1878(2) 0.0289(10) Uani 1 1 d . . . H4A H 0.2236 0.0009 0.1643 0.035 Uiso 1 1 calc R . . H4B H 0.2287 -0.0526 0.2423 0.035 Uiso 1 1 calc R . . C5 C 0.15485(18) 0.0618(4) 0.1838(2) 0.0245(9) Uani 1 1 d . . . C6 C 0.0587(2) -0.1679(4) 0.2230(3) 0.0377(12) Uani 1 1 d . . . H6A H 0.0254 -0.1141 0.2159 0.057 Uiso 1 1 calc R . . H6B H 0.0891 -0.1682 0.2772 0.057 Uiso 1 1 calc R . . H6C H 0.0440 -0.2529 0.2068 0.057 Uiso 1 1 calc R . . C7 C 0.03663(19) -0.1127(4) 0.0910(2) 0.0301(10) Uani 1 1 d . . . H7A H 0.0090 -0.0449 0.0850 0.045 Uiso 1 1 calc R . . H7B H 0.0148 -0.1918 0.0765 0.045 Uiso 1 1 calc R . . H7C H 0.0547 -0.0971 0.0580 0.045 Uiso 1 1 calc R . . C8 C 0.1882(2) 0.1649(4) 0.2420(2) 0.0333(11) Uani 1 1 d . . . H8A H 0.2070 0.1301 0.2939 0.050 Uiso 1 1 calc R . . H8B H 0.1600 0.2304 0.2377 0.050 Uiso 1 1 calc R . . H8C H 0.2190 0.2003 0.2316 0.050 Uiso 1 1 calc R . . C9 C 0.1221(2) 0.1208(4) 0.1037(2) 0.0317(10) Uani 1 1 d . . . H9A H 0.1067 0.0549 0.0648 0.048 Uiso 1 1 calc R . . H9B H 0.1499 0.1734 0.0954 0.048 Uiso 1 1 calc R . . H9C H 0.0888 0.1716 0.0996 0.048 Uiso 1 1 calc R . . C11 C 0.11615(18) 0.5084(4) 0.5017(2) 0.0227(9) Uani 1 1 d . . . C12 C 0.16953(18) 0.5380(4) 0.5807(2) 0.0275(10) Uani 1 1 d . . . H12A H 0.1558 0.5922 0.6094 0.033 Uiso 1 1 calc R . . H12B H 0.1844 0.4594 0.6099 0.033 Uiso 1 1 calc R . . C13 C 0.2204(2) 0.6020(4) 0.5756(2) 0.0324(11) Uani 1 1 d . . . H13A H 0.2541 0.6158 0.6277 0.039 Uiso 1 1 calc R . . H13B H 0.2070 0.6841 0.5503 0.039 Uiso 1 1 calc R . . C14 C 0.24099(18) 0.5210(4) 0.5295(2) 0.0299(10) Uani 1 1 d . . . H14A H 0.2576 0.4421 0.5576 0.036 Uiso 1 1 calc R . . H14B H 0.2733 0.5647 0.5249 0.036 Uiso 1 1 calc R . . C15 C 0.19041(18) 0.4909(4) 0.4492(2) 0.0250(9) Uani 1 1 d . . . C16 C 0.07505(19) 0.4188(4) 0.5132(2) 0.0291(10) Uani 1 1 d . . . H16A H 0.0389 0.4052 0.4641 0.044 Uiso 1 1 calc R . . H16B H 0.0642 0.4541 0.5502 0.044 Uiso 1 1 calc R . . H16C H 0.0956 0.3391 0.5326 0.044 Uiso 1 1 calc R . . C17 C 0.0807(2) 0.6258(4) 0.4634(2) 0.0312(10) Uani 1 1 d . . . H17A H 0.0499 0.6062 0.4110 0.047 Uiso 1 1 calc R . . H17B H 0.1076 0.6894 0.4619 0.047 Uiso 1 1 calc R . . H17C H 0.0617 0.6573 0.4927 0.047 Uiso 1 1 calc R . . C18 C 0.2111(2) 0.3861(4) 0.4150(2) 0.0299(10) Uani 1 1 d . . . H18A H 0.2138 0.3080 0.4419 0.045 Uiso 1 1 calc R . . H18B H 0.2504 0.4070 0.4206 0.045 Uiso 1 1 calc R . . H18C H 0.1823 0.3765 0.3605 0.045 Uiso 1 1 calc R . . C19 C 0.1758(2) 0.6050(4) 0.3964(2) 0.0327(11) Uani 1 1 d . . . H19A H 0.1666 0.6763 0.4197 0.049 Uiso 1 1 calc R . . H19B H 0.1411 0.5863 0.3466 0.049 Uiso 1 1 calc R . . H19C H 0.2102 0.6249 0.3891 0.049 Uiso 1 1 calc R . . H98 H 0.1278(15) -0.006(3) 0.2524(7) 0.016(10) Uiso 1 1 d D . . H99 H 0.1458(17) 0.3725(17) 0.469(2) 0.022(12) Uiso 1 1 d 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 Li1 0.027(4) 0.027(4) 0.033(4) -0.004(3) 0.019(3) 0.000(3) Li2 0.031(4) 0.025(4) 0.025(4) 0.001(3) 0.015(3) -0.004(3) I1 0.02232(15) 0.01964(14) 0.02426(14) 0.00044(10) 0.00891(11) -0.00068(12) I2 0.02399(16) 0.02441(14) 0.02307(14) 0.00249(10) 0.01049(11) -0.00032(12) N1 0.0211(19) 0.0198(17) 0.0181(17) -0.0008(13) 0.0110(15) -0.0031(15) N2 0.0229(19) 0.0165(17) 0.0248(17) -0.0013(14) 0.0143(15) 0.0002(16) C1 0.025(2) 0.0170(19) 0.030(2) -0.0062(16) 0.0156(19) -0.0040(18) C2 0.034(3) 0.021(2) 0.027(2) 0.0002(17) 0.016(2) 0.005(2) C3 0.028(3) 0.025(2) 0.035(2) 0.0036(18) 0.017(2) 0.003(2) C4 0.025(2) 0.034(2) 0.032(2) -0.0024(19) 0.0165(19) -0.001(2) C5 0.020(2) 0.026(2) 0.027(2) -0.0002(17) 0.0105(18) -0.0023(19) C6 0.050(3) 0.022(2) 0.058(3) 0.002(2) 0.039(3) -0.007(2) C7 0.027(3) 0.027(2) 0.035(2) -0.0089(18) 0.014(2) -0.007(2) C8 0.029(3) 0.029(2) 0.042(3) -0.007(2) 0.017(2) -0.006(2) C9 0.036(3) 0.029(2) 0.031(2) 0.0078(19) 0.017(2) -0.001(2) C11 0.020(2) 0.024(2) 0.021(2) -0.0037(16) 0.0078(17) 0.0024(19) C12 0.026(2) 0.031(2) 0.024(2) -0.0034(18) 0.0102(18) 0.002(2) C13 0.030(3) 0.028(2) 0.027(2) -0.0049(18) 0.004(2) -0.003(2) C14 0.022(2) 0.032(2) 0.030(2) -0.0007(19) 0.0082(19) -0.006(2) C15 0.022(2) 0.026(2) 0.027(2) -0.0005(17) 0.0126(18) -0.004(2) C16 0.028(2) 0.035(2) 0.026(2) -0.0015(18) 0.0154(19) 0.000(2) C17 0.031(3) 0.028(2) 0.027(2) -0.0049(18) 0.009(2) 0.010(2) C18 0.027(3) 0.034(2) 0.033(2) 0.0056(19) 0.018(2) 0.003(2) C19 0.037(3) 0.028(2) 0.035(2) 0.0013(19) 0.019(2) -0.010(2) _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 Li1 N1 2.112(8) . ? Li1 I1 2.843(7) 2 ? Li1 I1 2.879(7) . ? Li1 I2 2.907(7) . ? Li1 H98 2.32(3) . ? Li2 N2 2.096(8) . ? Li2 I2 2.799(7) . ? Li2 I2 2.814(7) 2 ? Li2 I1 2.843(7) . ? Li2 H99 2.31(4) . ? I1 Li1 2.843(7) 2 ? I2 Li2 2.814(7) 2 ? N1 C5 1.502(5) . ? N1 C1 1.507(5) . ? N1 H98 0.842(10) . ? N2 C11 1.498(5) . ? N2 C15 1.502(5) . ? N2 H99 0.835(10) . ? C1 C6 1.515(5) . ? C1 C7 1.536(6) . ? C1 C2 1.536(5) . ? C2 C3 1.519(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.521(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.531(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C8 1.531(5) . ? C5 C9 1.536(5) . ? 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 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C11 C16 1.519(5) . ? C11 C17 1.525(5) . ? C11 C12 1.540(5) . ? C12 C13 1.515(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.526(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.530(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C18 1.534(5) . ? C15 C19 1.538(5) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 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 N1 Li1 I1 125.9(3) . 2 ? N1 Li1 I1 102.4(3) . . ? I1 Li1 I1 102.3(2) 2 . ? N1 Li1 I2 124.9(3) . . ? I1 Li1 I2 97.7(2) 2 . ? I1 Li1 I2 98.5(2) . . ? N1 Li1 H98 21.2(5) . . ? I1 Li1 H98 134.4(9) 2 . ? I1 Li1 H98 81.3(5) . . ? I2 Li1 H98 127.1(10) . . ? N2 Li2 I2 125.1(3) . . ? N2 Li2 I2 126.6(3) . 2 ? I2 Li2 I2 97.0(2) . 2 ? N2 Li2 I1 101.2(3) . . ? I2 Li2 I1 101.9(2) . . ? I2 Li2 I1 99.9(2) 2 . ? N2 Li2 H99 21.1(5) . . ? I2 Li2 H99 131.5(11) . . ? I2 Li2 H99 130.8(11) 2 . ? I1 Li2 H99 80.1(5) . . ? Li1 I1 Li2 80.4(2) 2 . ? Li1 I1 Li1 77.1(2) 2 . ? Li2 I1 Li1 79.0(2) . . ? Li2 I2 Li2 81.8(2) . 2 ? Li2 I2 Li1 79.24(19) . . ? Li2 I2 Li1 79.77(19) 2 . ? C5 N1 C1 117.3(3) . . ? C5 N1 Li1 116.0(3) . . ? C1 N1 Li1 116.3(3) . . ? C5 N1 H98 108(3) . . ? C1 N1 H98 100(3) . . ? Li1 N1 H98 94(3) . . ? C11 N2 C15 117.9(3) . . ? C11 N2 Li2 114.4(3) . . ? C15 N2 Li2 117.6(3) . . ? C11 N2 H99 105(3) . . ? C15 N2 H99 102(3) . . ? Li2 N2 H99 94(3) . . ? N1 C1 C6 107.0(3) . . ? N1 C1 C7 110.8(3) . . ? C6 C1 C7 108.5(4) . . ? N1 C1 C2 111.6(3) . . ? C6 C1 C2 109.0(3) . . ? C7 C1 C2 109.9(3) . . ? C3 C2 C1 112.6(3) . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C4 108.5(3) . . ? C2 C3 H3A 110.0 . . ? C4 C3 H3A 110.0 . . ? C2 C3 H3B 110.0 . . ? C4 C3 H3B 110.0 . . ? H3A C3 H3B 108.4 . . ? C3 C4 C5 113.4(3) . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? C3 C4 H4B 108.9 . . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? N1 C5 C8 106.5(3) . . ? N1 C5 C4 112.8(3) . . ? C8 C5 C4 108.5(3) . . ? N1 C5 C9 109.8(3) . . ? C8 C5 C9 108.3(3) . . ? C4 C5 C9 110.8(3) . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C1 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 . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C11 C16 106.6(3) . . ? N2 C11 C17 110.7(3) . . ? C16 C11 C17 108.1(4) . . ? N2 C11 C12 111.9(3) . . ? C16 C11 C12 108.3(3) . . ? C17 C11 C12 111.2(3) . . ? C13 C12 C11 113.1(3) . . ? C13 C12 H12A 109.0 . . ? C11 C12 H12A 109.0 . . ? C13 C12 H12B 109.0 . . ? C11 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? C12 C13 C14 109.6(3) . . ? C12 C13 H13A 109.8 . . ? C14 C13 H13A 109.8 . . ? C12 C13 H13B 109.8 . . ? C14 C13 H13B 109.8 . . ? H13A C13 H13B 108.2 . . ? C13 C14 C15 112.6(4) . . ? C13 C14 H14A 109.1 . . ? C15 C14 H14A 109.1 . . ? C13 C14 H14B 109.1 . . ? C15 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? N2 C15 C14 112.5(3) . . ? N2 C15 C18 106.5(3) . . ? C14 C15 C18 108.7(3) . . ? N2 C15 C19 110.8(3) . . ? C14 C15 C19 110.6(3) . . ? C18 C15 C19 107.6(3) . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C11 C17 H17A 109.5 . . ? C11 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C11 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C15 C19 H19A 109.5 . . ? C15 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C15 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Li2 I1 Li1 142.3(3) . . . 2 ? I2 Li2 I1 Li1 -87.8(2) . . . 2 ? I2 Li2 I1 Li1 11.6(2) 2 . . 2 ? N2 Li2 I1 Li1 -139.1(3) . . . . ? I2 Li2 I1 Li1 -9.2(2) . . . . ? I2 Li2 I1 Li1 90.2(2) 2 . . . ? N1 Li1 I1 Li1 -140.1(2) . . . 2 ? I1 Li1 I1 Li1 -8.6(3) 2 . . 2 ? I2 Li1 I1 Li1 91.30(18) . . . 2 ? N1 Li1 I1 Li2 137.4(3) . . . . ? I1 Li1 I1 Li2 -91.1(2) 2 . . . ? I2 Li1 I1 Li2 8.8(2) . . . . ? N2 Li2 I2 Li2 -156.9(3) . . . 2 ? I2 Li2 I2 Li2 -11.5(3) 2 . . 2 ? I1 Li2 I2 Li2 90.2(2) . . . 2 ? N2 Li2 I2 Li1 122.1(4) . . . . ? I2 Li2 I2 Li1 -92.6(2) 2 . . . ? I1 Li2 I2 Li1 9.1(2) . . . . ? N1 Li1 I2 Li2 -120.5(4) . . . . ? I1 Li1 I2 Li2 94.8(2) 2 . . . ? I1 Li1 I2 Li2 -8.9(2) . . . . ? N1 Li1 I2 Li2 156.0(4) . . . 2 ? I1 Li1 I2 Li2 11.3(2) 2 . . 2 ? I1 Li1 I2 Li2 -92.4(2) . . . 2 ? I1 Li1 N1 C5 125.9(4) 2 . . . ? I1 Li1 N1 C5 -118.8(3) . . . . ? I2 Li1 N1 C5 -9.1(5) . . . . ? I1 Li1 N1 C1 -18.3(5) 2 . . . ? I1 Li1 N1 C1 97.0(3) . . . . ? I2 Li1 N1 C1 -153.3(3) . . . . ? I2 Li2 N2 C11 135.7(3) . . . . ? I2 Li2 N2 C11 0.4(5) 2 . . . ? I1 Li2 N2 C11 -111.0(3) . . . . ? I2 Li2 N2 C15 -9.1(5) . . . . ? I2 Li2 N2 C15 -144.4(3) 2 . . . ? I1 Li2 N2 C15 104.2(3) . . . . ? C5 N1 C1 C6 162.4(3) . . . . ? Li1 N1 C1 C6 -53.9(4) . . . . ? C5 N1 C1 C7 -79.6(4) . . . . ? Li1 N1 C1 C7 64.2(4) . . . . ? C5 N1 C1 C2 43.2(4) . . . . ? Li1 N1 C1 C2 -173.1(3) . . . . ? N1 C1 C2 C3 -52.3(5) . . . . ? C6 C1 C2 C3 -170.3(3) . . . . ? C7 C1 C2 C3 71.0(4) . . . . ? C1 C2 C3 C4 59.3(5) . . . . ? C2 C3 C4 C5 -57.1(5) . . . . ? C1 N1 C5 C8 -160.2(3) . . . . ? Li1 N1 C5 C8 56.0(4) . . . . ? C1 N1 C5 C4 -41.3(5) . . . . ? Li1 N1 C5 C4 174.9(3) . . . . ? C1 N1 C5 C9 82.7(4) . . . . ? Li1 N1 C5 C9 -61.1(4) . . . . ? C3 C4 C5 N1 48.3(5) . . . . ? C3 C4 C5 C8 166.0(4) . . . . ? C3 C4 C5 C9 -75.3(4) . . . . ? C15 N2 C11 C16 -160.7(3) . . . . ? Li2 N2 C11 C16 54.6(4) . . . . ? C15 N2 C11 C17 82.0(4) . . . . ? Li2 N2 C11 C17 -62.7(4) . . . . ? C15 N2 C11 C12 -42.5(5) . . . . ? Li2 N2 C11 C12 172.8(3) . . . . ? N2 C11 C12 C13 49.6(4) . . . . ? C16 C11 C12 C13 166.7(3) . . . . ? C17 C11 C12 C13 -74.7(4) . . . . ? C11 C12 C13 C14 -57.1(5) . . . . ? C12 C13 C14 C15 56.8(5) . . . . ? C11 N2 C15 C14 42.7(5) . . . . ? Li2 N2 C15 C14 -173.7(3) . . . . ? C11 N2 C15 C18 161.7(3) . . . . ? Li2 N2 C15 C18 -54.7(4) . . . . ? C11 N2 C15 C19 -81.6(4) . . . . ? Li2 N2 C15 C19 61.9(4) . . . . ? C13 C14 C15 N2 -49.2(5) . . . . ? C13 C14 C15 C18 -166.8(3) . . . . ? C13 C14 C15 C19 75.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.915 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.070 _refine_diff_density_min -0.600 _refine_diff_density_rms 0.133 #===END #----------------------------------------------- #---------------COMPOUND 6---------------------- #----------------------------------------------- data_srec1107 _database_code_depnum_ccdc_archive 'CCDC 847969' #TrackingRef '- Combined.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H44 Al N O' _chemical_formula_sum 'C21 H44 Al N O' _chemical_formula_weight 353.55 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.4710(2) _cell_length_b 12.1167(2) _cell_length_c 35.1416(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4458.55(14) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 7722 _cell_measurement_theta_min 3.0979 _cell_measurement_theta_max 28.4107 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.053 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_T_min 0.64584 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Xcalibur, Eos' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16838 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0523 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 28.47 _reflns_number_total 5203 _reflns_number_gt 3858 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0283P)^2^+2.8428P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5203 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0824 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.1126 _refine_ls_wR_factor_gt 0.1040 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _refine_ls_shift/su_max 0.000 _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 Al1 Al 0.04837(5) 0.70699(4) 0.383442(15) 0.01382(13) Uani 1 1 d . . . N1 N 0.01229(14) 0.72994(11) 0.33209(4) 0.0147(3) Uani 1 1 d . . . C1 C -0.07336(19) 0.82054(14) 0.31865(5) 0.0188(4) Uani 1 1 d . . . C2 C -0.0474(2) 0.85292(15) 0.27710(5) 0.0249(5) Uani 1 1 d . . . H2A H -0.1147 0.9048 0.2687 0.030 Uiso 1 1 calc R . . H2B H 0.0353 0.8925 0.2759 0.030 Uiso 1 1 calc R . . C3 C -0.0432(2) 0.75671(15) 0.24963(6) 0.0272(5) Uani 1 1 d . . . H3A H -0.1280 0.7208 0.2482 0.033 Uiso 1 1 calc R . . H3B H -0.0197 0.7828 0.2239 0.033 Uiso 1 1 calc R . . C4 C 0.0554(2) 0.67572(15) 0.26409(5) 0.0223(4) Uani 1 1 d . . . H4A H 0.1406 0.7111 0.2633 0.027 Uiso 1 1 calc R . . H4B H 0.0576 0.6111 0.2469 0.027 Uiso 1 1 calc R . . C5 C 0.02909(18) 0.63561(14) 0.30504(5) 0.0169(4) Uani 1 1 d . . . C6 C -0.2162(2) 0.79363(17) 0.32363(6) 0.0315(5) Uani 1 1 d . . . H6A H -0.2320 0.7699 0.3499 0.047 Uiso 1 1 calc R . . H6B H -0.2402 0.7343 0.3061 0.047 Uiso 1 1 calc R . . H6C H -0.2671 0.8596 0.3181 0.047 Uiso 1 1 calc R . . C7 C -0.0476(2) 0.92629(15) 0.34127(6) 0.0292(5) Uani 1 1 d . . . H7A H -0.0792 0.9174 0.3673 0.044 Uiso 1 1 calc R . . H7B H -0.0916 0.9884 0.3291 0.044 Uiso 1 1 calc R . . H7C H 0.0444 0.9408 0.3418 0.044 Uiso 1 1 calc R . . C8 C 0.14728(19) 0.56844(14) 0.31618(5) 0.0211(4) Uani 1 1 d . . . H8A H 0.2230 0.6159 0.3152 0.032 Uiso 1 1 calc R . . H8B H 0.1579 0.5068 0.2984 0.032 Uiso 1 1 calc R . . H8C H 0.1366 0.5397 0.3421 0.032 Uiso 1 1 calc R . . C9 C -0.0853(2) 0.55525(15) 0.30432(6) 0.0240(4) Uani 1 1 d . . . H9A H -0.1570 0.5897 0.2909 0.036 Uiso 1 1 calc R . . H9B H -0.1109 0.5377 0.3305 0.036 Uiso 1 1 calc R . . H9C H -0.0606 0.4873 0.2911 0.036 Uiso 1 1 calc R . . C10 C 0.0145(2) 0.82166(15) 0.42278(5) 0.0189(4) Uani 1 1 d . . . C11 C 0.07605(19) 0.80098(14) 0.46209(5) 0.0213(4) Uani 1 1 d . . . H11A H 0.0961 0.7205 0.4641 0.026 Uiso 1 1 calc R . . C12 C -0.0139(2) 0.83096(18) 0.49462(6) 0.0336(5) Uani 1 1 d . . . H12A H 0.0291 0.8180 0.5190 0.050 Uiso 1 1 calc R . . H12B H -0.0909 0.7852 0.4931 0.050 Uiso 1 1 calc R . . H12C H -0.0376 0.9090 0.4926 0.050 Uiso 1 1 calc R . . C13 C 0.2005(2) 0.86468(16) 0.46611(6) 0.0281(5) Uani 1 1 d . . . H13A H 0.2401 0.8471 0.4907 0.042 Uiso 1 1 calc R . . H13B H 0.1830 0.9440 0.4648 0.042 Uiso 1 1 calc R . . H13C H 0.2587 0.8439 0.4455 0.042 Uiso 1 1 calc R . . C14 C 0.01386(19) 0.55867(14) 0.40699(5) 0.0169(4) Uani 1 1 d . . . C15 C -0.09498(18) 0.55330(14) 0.43638(5) 0.0183(4) Uani 1 1 d . . . H15A H -0.0774 0.6100 0.4564 0.022 Uiso 1 1 calc R . . C16 C -0.2226(2) 0.58059(18) 0.41840(6) 0.0332(5) Uani 1 1 d . . . H16A H -0.2902 0.5742 0.4376 0.050 Uiso 1 1 calc R . . H16B H -0.2396 0.5291 0.3975 0.050 Uiso 1 1 calc R . . H16C H -0.2206 0.6562 0.4085 0.050 Uiso 1 1 calc R . . C17 C -0.1027(2) 0.44103(16) 0.45593(6) 0.0322(5) Uani 1 1 d . . . H17A H -0.1687 0.4431 0.4757 0.048 Uiso 1 1 calc R . . H17B H -0.0201 0.4235 0.4675 0.048 Uiso 1 1 calc R . . H17C H -0.1244 0.3843 0.4371 0.048 Uiso 1 1 calc R . . O1 O 0.23460(11) 0.71143(9) 0.38300(3) 0.0168(3) Uani 1 1 d . . . C18 C 0.32330(18) 0.63803(15) 0.40295(5) 0.0205(4) Uani 1 1 d . . . H18A H 0.3188 0.5623 0.3925 0.025 Uiso 1 1 calc R . . H18B H 0.3034 0.6353 0.4305 0.025 Uiso 1 1 calc R . . C19 C 0.45360(19) 0.68757(16) 0.39635(6) 0.0251(4) Uani 1 1 d . . . H19A H 0.5201 0.6296 0.3951 0.030 Uiso 1 1 calc R . . H19B H 0.4759 0.7407 0.4167 0.030 Uiso 1 1 calc R . . C20 C 0.43878(19) 0.74575(17) 0.35799(5) 0.0244(4) Uani 1 1 d . . . H20A H 0.5034 0.8046 0.3547 0.029 Uiso 1 1 calc R . . H20B H 0.4454 0.6929 0.3366 0.029 Uiso 1 1 calc R . . C21 C 0.30609(19) 0.79307(14) 0.36103(5) 0.0208(4) Uani 1 1 d . . . H21A H 0.3075 0.8651 0.3743 0.025 Uiso 1 1 calc R . . H21B H 0.2679 0.8032 0.3355 0.025 Uiso 1 1 calc R . . H14A H 0.091(2) 0.5333(15) 0.4189(5) 0.022(5) Uiso 1 1 d . . . H14B H -0.002(2) 0.5049(17) 0.3875(6) 0.031(6) Uiso 1 1 d . . . H10A H 0.039(2) 0.8967(18) 0.4144(6) 0.035(6) Uiso 1 1 d . . . H10B H -0.077(2) 0.8254(17) 0.4263(6) 0.036(6) 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 Al1 0.0137(3) 0.0134(2) 0.0144(3) 0.0006(2) -0.0002(2) 0.0005(2) N1 0.0166(8) 0.0131(6) 0.0144(7) -0.0010(5) -0.0015(6) 0.0035(6) C1 0.0219(11) 0.0182(8) 0.0163(9) 0.0021(7) -0.0040(8) 0.0042(8) C2 0.0317(12) 0.0238(9) 0.0191(10) 0.0043(8) -0.0062(9) 0.0022(9) C3 0.0358(12) 0.0294(9) 0.0165(9) 0.0025(8) -0.0033(9) -0.0024(10) C4 0.0266(11) 0.0254(9) 0.0150(9) -0.0035(7) 0.0032(9) -0.0033(9) C5 0.0201(10) 0.0167(8) 0.0140(8) -0.0030(7) 0.0015(8) -0.0007(8) C6 0.0223(12) 0.0368(11) 0.0354(12) 0.0067(10) -0.0009(10) 0.0113(10) C7 0.0446(14) 0.0198(9) 0.0233(10) -0.0001(8) -0.0080(10) 0.0112(10) C8 0.0232(11) 0.0200(8) 0.0202(9) -0.0034(7) 0.0027(9) 0.0033(8) C9 0.0262(11) 0.0215(9) 0.0243(10) -0.0034(8) 0.0015(9) -0.0060(9) C10 0.0220(11) 0.0169(8) 0.0179(9) -0.0015(7) -0.0016(9) 0.0016(8) C11 0.0301(12) 0.0172(8) 0.0167(9) -0.0013(7) -0.0008(8) 0.0007(8) C12 0.0431(14) 0.0346(10) 0.0232(11) -0.0028(9) 0.0068(11) -0.0087(11) C13 0.0306(12) 0.0306(10) 0.0232(10) -0.0035(8) -0.0063(9) -0.0014(10) C14 0.0159(10) 0.0154(8) 0.0194(9) 0.0010(7) 0.0009(8) 0.0010(8) C15 0.0182(10) 0.0179(8) 0.0188(9) 0.0006(7) 0.0016(8) -0.0013(8) C16 0.0202(12) 0.0455(12) 0.0339(12) 0.0095(10) 0.0020(10) -0.0027(10) C17 0.0325(13) 0.0270(10) 0.0371(12) 0.0099(9) 0.0128(11) 0.0016(10) O1 0.0134(7) 0.0174(5) 0.0196(6) 0.0059(5) -0.0005(6) -0.0001(5) C18 0.0181(10) 0.0231(9) 0.0204(10) 0.0060(8) -0.0042(8) 0.0040(8) C19 0.0167(10) 0.0337(10) 0.0249(10) 0.0016(8) -0.0029(9) 0.0015(9) C20 0.0175(10) 0.0322(10) 0.0236(10) 0.0016(9) 0.0031(8) -0.0044(9) C21 0.0201(10) 0.0196(8) 0.0227(10) 0.0069(8) 0.0007(8) -0.0052(8) _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 Al1 N1 1.8647(15) . ? Al1 O1 1.9508(13) . ? Al1 C10 1.9918(19) . ? Al1 C14 2.0112(18) . ? N1 C1 1.494(2) . ? N1 C5 1.497(2) . ? C1 C7 1.532(2) . ? C1 C2 1.536(2) . ? C1 C6 1.541(3) . ? C2 C3 1.514(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.513(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.544(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C8 1.532(3) . ? C5 C9 1.544(3) . ? 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 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.545(3) . ? C10 H10A 0.99(2) . ? C10 H10B 0.97(2) . ? C11 C13 1.521(3) . ? C11 C12 1.525(3) . ? C11 H11A 1.0000 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.539(3) . ? C14 H14A 0.96(2) . ? C14 H14B 0.96(2) . ? C15 C16 1.515(3) . ? C15 C17 1.526(2) . ? C15 H15A 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? O1 C21 1.461(2) . ? O1 C18 1.465(2) . ? C18 C19 1.509(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.529(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.507(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? 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 N1 Al1 O1 100.99(6) . . ? N1 Al1 C10 122.11(7) . . ? O1 Al1 C10 99.47(8) . . ? N1 Al1 C14 119.67(7) . . ? O1 Al1 C14 101.97(7) . . ? C10 Al1 C14 107.81(8) . . ? C1 N1 C5 115.53(14) . . ? C1 N1 Al1 122.48(11) . . ? C5 N1 Al1 118.48(11) . . ? N1 C1 C7 110.18(15) . . ? N1 C1 C2 112.44(15) . . ? C7 C1 C2 104.38(15) . . ? N1 C1 C6 113.04(15) . . ? C7 C1 C6 106.79(17) . . ? C2 C1 C6 109.51(16) . . ? C3 C2 C1 114.48(15) . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2B 108.6 . . ? C1 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C4 C3 C2 107.76(16) . . ? C4 C3 H3A 110.2 . . ? C2 C3 H3A 110.2 . . ? C4 C3 H3B 110.2 . . ? C2 C3 H3B 110.2 . . ? H3A C3 H3B 108.5 . . ? C3 C4 C5 113.29(16) . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? C3 C4 H4B 108.9 . . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? N1 C5 C8 109.77(14) . . ? N1 C5 C9 113.63(15) . . ? C8 C5 C9 107.20(14) . . ? N1 C5 C4 111.87(13) . . ? C8 C5 C4 105.14(15) . . ? C9 C5 C4 108.79(15) . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C1 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 . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 Al1 115.66(13) . . ? C11 C10 H10A 107.9(13) . . ? Al1 C10 H10A 112.9(12) . . ? C11 C10 H10B 107.9(13) . . ? Al1 C10 H10B 107.3(13) . . ? H10A C10 H10B 104.6(18) . . ? C13 C11 C12 109.78(16) . . ? C13 C11 C10 111.00(16) . . ? C12 C11 C10 111.96(17) . . ? C13 C11 H11A 108.0 . . ? C12 C11 H11A 108.0 . . ? C10 C11 H11A 108.0 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 Al1 116.54(12) . . ? C15 C14 H14A 108.6(12) . . ? Al1 C14 H14A 108.2(11) . . ? C15 C14 H14B 108.7(13) . . ? Al1 C14 H14B 110.1(12) . . ? H14A C14 H14B 103.9(17) . . ? C16 C15 C17 109.60(17) . . ? C16 C15 C14 111.35(16) . . ? C17 C15 C14 112.28(15) . . ? C16 C15 H15A 107.8 . . ? C17 C15 H15A 107.8 . . ? C14 C15 H15A 107.8 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C21 O1 C18 109.82(13) . . ? C21 O1 Al1 122.34(10) . . ? C18 O1 Al1 127.84(10) . . ? O1 C18 C19 104.97(14) . . ? O1 C18 H18A 110.8 . . ? C19 C18 H18A 110.8 . . ? O1 C18 H18B 110.8 . . ? C19 C18 H18B 110.8 . . ? H18A C18 H18B 108.8 . . ? C18 C19 C20 103.14(15) . . ? C18 C19 H19A 111.1 . . ? C20 C19 H19A 111.1 . . ? C18 C19 H19B 111.1 . . ? C20 C19 H19B 111.1 . . ? H19A C19 H19B 109.1 . . ? C21 C20 C19 101.92(15) . . ? C21 C20 H20A 111.4 . . ? C19 C20 H20A 111.4 . . ? C21 C20 H20B 111.4 . . ? C19 C20 H20B 111.4 . . ? H20A C20 H20B 109.2 . . ? O1 C21 C20 104.61(14) . . ? O1 C21 H21A 110.8 . . ? C20 C21 H21A 110.8 . . ? O1 C21 H21B 110.8 . . ? C20 C21 H21B 110.8 . . ? H21A C21 H21B 108.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Al1 N1 C1 -124.99(13) . . . . ? C10 Al1 N1 C1 -16.35(17) . . . . ? C14 Al1 N1 C1 124.28(14) . . . . ? O1 Al1 N1 C5 77.11(13) . . . . ? C10 Al1 N1 C5 -174.24(13) . . . . ? C14 Al1 N1 C5 -33.62(16) . . . . ? C5 N1 C1 C7 -160.59(16) . . . . ? Al1 N1 C1 C7 40.9(2) . . . . ? C5 N1 C1 C2 -44.6(2) . . . . ? Al1 N1 C1 C2 156.89(13) . . . . ? C5 N1 C1 C6 80.0(2) . . . . ? Al1 N1 C1 C6 -78.48(18) . . . . ? N1 C1 C2 C3 50.1(2) . . . . ? C7 C1 C2 C3 169.50(18) . . . . ? C6 C1 C2 C3 -76.5(2) . . . . ? C1 C2 C3 C4 -55.5(2) . . . . ? C2 C3 C4 C5 56.9(2) . . . . ? C1 N1 C5 C8 162.57(15) . . . . ? Al1 N1 C5 C8 -38.03(18) . . . . ? C1 N1 C5 C9 -77.41(19) . . . . ? Al1 N1 C5 C9 81.99(17) . . . . ? C1 N1 C5 C4 46.3(2) . . . . ? Al1 N1 C5 C4 -154.34(13) . . . . ? C3 C4 C5 N1 -53.3(2) . . . . ? C3 C4 C5 C8 -172.38(15) . . . . ? C3 C4 C5 C9 73.06(19) . . . . ? N1 Al1 C10 C11 -167.01(13) . . . . ? O1 Al1 C10 C11 -57.57(15) . . . . ? C14 Al1 C10 C11 48.36(17) . . . . ? Al1 C10 C11 C13 97.55(16) . . . . ? Al1 C10 C11 C12 -139.38(15) . . . . ? N1 Al1 C14 C15 -111.47(14) . . . . ? O1 Al1 C14 C15 138.34(14) . . . . ? C10 Al1 C14 C15 34.17(17) . . . . ? Al1 C14 C15 C16 63.57(19) . . . . ? Al1 C14 C15 C17 -173.11(14) . . . . ? N1 Al1 O1 C21 42.59(13) . . . . ? C10 Al1 O1 C21 -82.95(13) . . . . ? C14 Al1 O1 C21 166.42(13) . . . . ? N1 Al1 O1 C18 -136.82(13) . . . . ? C10 Al1 O1 C18 97.64(14) . . . . ? C14 Al1 O1 C18 -12.99(15) . . . . ? C21 O1 C18 C19 7.21(19) . . . . ? Al1 O1 C18 C19 -173.32(11) . . . . ? O1 C18 C19 C20 -28.72(19) . . . . ? C18 C19 C20 C21 39.01(19) . . . . ? C18 O1 C21 C20 17.66(18) . . . . ? Al1 O1 C21 C20 -161.84(11) . . . . ? C19 C20 C21 O1 -34.74(18) . . . . ? _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.308 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.049 #===END #----------------------------------------------- #---------------COMPOUND 8---------------------- #----------------------------------------------- data_srec1108 _database_code_depnum_ccdc_archive 'CCDC 847970' #TrackingRef '- Combined.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H24 I N O' _chemical_formula_sum 'C16 H24 I N O' _chemical_formula_weight 373.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'F d d 2' 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 12.8821(5) _cell_length_b 59.0714(18) _cell_length_c 8.4330(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6417.2(4) _cell_formula_units_Z 16 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 12084 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 29.30 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.545 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3008 _exptl_absorpt_coefficient_mu 1.990 _exptl_absorpt_correction_T_min 0.44222 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15680 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -79 _diffrn_reflns_limit_k_max 79 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 29.37 _reflns_number_total 4065 _reflns_number_gt 3931 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0212P)^2^+1.5282P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.005(16) _refine_ls_number_reflns 4065 _refine_ls_number_parameters 177 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0224 _refine_ls_R_factor_gt 0.0212 _refine_ls_wR_factor_ref 0.0473 _refine_ls_wR_factor_gt 0.0468 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 I1 I 0.710106(12) 0.063375(2) 0.56637(3) 0.02226(5) Uani 1 1 d . . . O1 O 0.58810(13) 0.10742(3) 0.5444(2) 0.0191(4) Uani 1 1 d . . . N1 N 0.73728(14) 0.05249(3) 0.1922(2) 0.0133(4) Uani 1 1 d . . . C1 C 0.60338(17) 0.10117(4) 0.3896(3) 0.0152(5) Uani 1 1 d . . . C2 C 0.65824(16) 0.08115(4) 0.3648(3) 0.0133(4) Uani 1 1 d . . . C3 C 0.67812(17) 0.07290(4) 0.2117(3) 0.0127(4) Uani 1 1 d . . . C4 C 0.63895(17) 0.08535(4) 0.0844(3) 0.0187(5) Uani 1 1 d . . . H4 H 0.6502 0.0801 -0.0208 0.022 Uiso 1 1 calc R . . C5 C 0.5843(2) 0.10508(5) 0.1090(3) 0.0226(6) Uani 1 1 d . . . H5 H 0.5582 0.1133 0.0206 0.027 Uiso 1 1 calc R . . C6 C 0.56667(18) 0.11321(4) 0.2614(3) 0.0205(5) Uani 1 1 d . . . H6 H 0.5297 0.1269 0.2770 0.025 Uiso 1 1 calc R . . C7 C 0.53421(19) 0.12813(5) 0.5721(4) 0.0313(6) Uani 1 1 d . . . H7A H 0.5731 0.1407 0.5246 0.047 Uiso 1 1 calc R . . H7B H 0.5275 0.1306 0.6865 0.047 Uiso 1 1 calc R . . H7C H 0.4650 0.1273 0.5241 0.047 Uiso 1 1 calc R . . C10 C 0.84785(19) 0.05539(4) 0.1429(3) 0.0168(5) Uani 1 1 d . . . C11 C 0.90473(19) 0.03339(4) 0.1864(3) 0.0215(5) Uani 1 1 d . . . H11A H 0.9767 0.0342 0.1456 0.026 Uiso 1 1 calc R . . H11B H 0.9084 0.0321 0.3033 0.026 Uiso 1 1 calc R . . C12 C 0.85253(19) 0.01247(4) 0.1203(3) 0.0240(5) Uani 1 1 d . . . H12A H 0.8911 -0.0012 0.1538 0.029 Uiso 1 1 calc R . . H12B H 0.8525 0.0131 0.0030 0.029 Uiso 1 1 calc R . . C13 C 0.74138(19) 0.01131(4) 0.1813(3) 0.0225(5) Uani 1 1 d . . . H13A H 0.7426 0.0096 0.2981 0.027 Uiso 1 1 calc R . . H13B H 0.7072 -0.0023 0.1364 0.027 Uiso 1 1 calc R . . C14 C 0.67736(19) 0.03222(4) 0.1387(3) 0.0180(5) Uani 1 1 d . . . C15 C 0.8649(2) 0.06094(5) -0.0341(3) 0.0239(6) Uani 1 1 d . . . H15A H 0.8481 0.0476 -0.0985 0.036 Uiso 1 1 calc R . . H15B H 0.9376 0.0652 -0.0514 0.036 Uiso 1 1 calc R . . H15C H 0.8198 0.0736 -0.0649 0.036 Uiso 1 1 calc R . . C16 C 0.8966(2) 0.07468(5) 0.2381(4) 0.0274(6) Uani 1 1 d . . . H16A H 0.8648 0.0891 0.2067 0.041 Uiso 1 1 calc R . . H16B H 0.9714 0.0752 0.2171 0.041 Uiso 1 1 calc R . . H16C H 0.8848 0.0721 0.3514 0.041 Uiso 1 1 calc R . . C17 C 0.6469(2) 0.03156(5) -0.0373(3) 0.0229(6) Uani 1 1 d . . . H17A H 0.6031 0.0447 -0.0621 0.034 Uiso 1 1 calc R . . H17B H 0.6085 0.0176 -0.0593 0.034 Uiso 1 1 calc R . . H17C H 0.7097 0.0320 -0.1028 0.034 Uiso 1 1 calc R . . C18 C 0.57561(19) 0.03123(4) 0.2333(4) 0.0256(6) Uani 1 1 d . . . H18A H 0.5911 0.0318 0.3470 0.038 Uiso 1 1 calc R . . H18B H 0.5391 0.0171 0.2088 0.038 Uiso 1 1 calc R . . H18C H 0.5318 0.0441 0.2044 0.038 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 I1 0.02879(8) 0.02301(7) 0.01496(7) 0.00185(7) -0.00058(7) 0.00752(7) O1 0.0206(8) 0.0170(8) 0.0197(9) -0.0045(7) 0.0024(7) 0.0044(7) N1 0.0145(9) 0.0088(8) 0.0167(10) -0.0004(7) 0.0013(8) 0.0008(8) C1 0.0132(10) 0.0122(10) 0.0203(11) -0.0050(9) 0.0014(9) -0.0018(9) C2 0.0125(10) 0.0115(10) 0.0158(11) 0.0032(8) -0.0005(8) -0.0014(9) C3 0.0118(10) 0.0085(10) 0.0179(11) 0.0004(8) 0.0011(9) -0.0011(9) C4 0.0204(10) 0.0207(10) 0.0151(11) 0.0028(10) 0.0022(10) 0.0021(9) C5 0.0219(12) 0.0225(12) 0.0235(14) 0.0080(10) 0.0020(10) 0.0057(11) C6 0.0170(11) 0.0164(11) 0.0281(13) 0.0000(9) 0.0033(9) 0.0033(10) C7 0.0321(14) 0.0289(13) 0.0330(14) -0.0132(14) 0.0009(15) 0.0150(11) C10 0.0134(11) 0.0154(12) 0.0215(12) -0.0018(10) 0.0035(9) 0.0012(10) C11 0.0189(12) 0.0234(13) 0.0222(13) 0.0009(10) 0.0019(10) 0.0062(11) C12 0.0269(13) 0.0186(11) 0.0266(12) 0.0005(9) 0.0013(10) 0.0110(11) C13 0.0286(13) 0.0115(11) 0.0275(13) 0.0007(9) 0.0034(11) 0.0017(10) C14 0.0194(12) 0.0113(10) 0.0232(12) -0.0029(9) 0.0010(10) -0.0009(10) C15 0.0217(13) 0.0246(13) 0.0255(14) 0.0079(12) 0.0112(11) 0.0050(11) C16 0.0179(12) 0.0266(14) 0.0378(15) -0.0052(12) 0.0046(11) -0.0045(11) C17 0.0240(13) 0.0195(12) 0.0253(13) -0.0075(11) -0.0046(11) 0.0034(11) C18 0.0234(12) 0.0170(12) 0.0364(14) -0.0064(11) 0.0065(12) -0.0071(11) _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 I1 C2 2.107(2) . ? O1 C1 1.371(3) . ? O1 C7 1.426(3) . ? N1 C3 1.436(3) . ? N1 C10 1.494(3) . ? N1 C14 1.494(3) . ? C1 C6 1.378(3) . ? C1 C2 1.394(3) . ? C2 C3 1.403(3) . ? C3 C4 1.396(3) . ? C4 C5 1.378(3) . ? C4 H4 0.9500 . ? C5 C6 1.391(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C10 C16 1.529(4) . ? C10 C11 1.536(3) . ? C10 C15 1.544(3) . ? C11 C12 1.513(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.523(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.528(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C17 1.535(3) . ? C14 C18 1.535(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 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 O1 C7 117.2(2) . . ? C3 N1 C10 116.20(19) . . ? C3 N1 C14 115.68(18) . . ? C10 N1 C14 120.02(18) . . ? O1 C1 C6 124.0(2) . . ? O1 C1 C2 116.4(2) . . ? C6 C1 C2 119.6(2) . . ? C1 C2 C3 121.7(2) . . ? C1 C2 I1 117.56(16) . . ? C3 C2 I1 120.77(16) . . ? C4 C3 C2 117.3(2) . . ? C4 C3 N1 123.1(2) . . ? C2 C3 N1 119.6(2) . . ? C5 C4 C3 121.0(2) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 121.0(2) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C1 C6 C5 119.4(2) . . ? C1 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C10 C16 109.3(2) . . ? N1 C10 C11 106.9(2) . . ? C16 C10 C11 108.0(2) . . ? N1 C10 C15 115.4(2) . . ? C16 C10 C15 106.9(2) . . ? C11 C10 C15 110.1(2) . . ? C12 C11 C10 113.0(2) . . ? C12 C11 H11A 109.0 . . ? C10 C11 H11A 109.0 . . ? C12 C11 H11B 109.0 . . ? C10 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? C11 C12 C13 109.3(2) . . ? C11 C12 H12A 109.8 . . ? C13 C12 H12A 109.8 . . ? C11 C12 H12B 109.8 . . ? C13 C12 H12B 109.8 . . ? H12A C12 H12B 108.3 . . ? C12 C13 C14 113.1(2) . . ? C12 C13 H13A 109.0 . . ? C14 C13 H13A 109.0 . . ? C12 C13 H13B 109.0 . . ? C14 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? N1 C14 C13 107.32(19) . . ? N1 C14 C17 116.4(2) . . ? C13 C14 C17 110.2(2) . . ? N1 C14 C18 108.33(19) . . ? C13 C14 C18 107.9(2) . . ? C17 C14 C18 106.4(2) . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C10 C16 H16A 109.5 . . ? C10 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C10 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 O1 C1 C6 -2.5(3) . . . . ? C7 O1 C1 C2 178.6(2) . . . . ? O1 C1 C2 C3 179.5(2) . . . . ? C6 C1 C2 C3 0.5(3) . . . . ? O1 C1 C2 I1 -0.1(3) . . . . ? C6 C1 C2 I1 -179.11(17) . . . . ? C1 C2 C3 C4 -1.2(3) . . . . ? I1 C2 C3 C4 178.42(16) . . . . ? C1 C2 C3 N1 178.4(2) . . . . ? I1 C2 C3 N1 -1.9(3) . . . . ? C10 N1 C3 C4 76.9(3) . . . . ? C14 N1 C3 C4 -71.9(3) . . . . ? C10 N1 C3 C2 -102.8(2) . . . . ? C14 N1 C3 C2 108.4(2) . . . . ? C2 C3 C4 C5 0.9(3) . . . . ? N1 C3 C4 C5 -178.8(2) . . . . ? C3 C4 C5 C6 0.1(4) . . . . ? O1 C1 C6 C5 -178.4(2) . . . . ? C2 C1 C6 C5 0.5(3) . . . . ? C4 C5 C6 C1 -0.8(4) . . . . ? C3 N1 C10 C16 43.5(3) . . . . ? C14 N1 C10 C16 -169.2(2) . . . . ? C3 N1 C10 C11 160.2(2) . . . . ? C14 N1 C10 C11 -52.4(3) . . . . ? C3 N1 C10 C15 -77.0(3) . . . . ? C14 N1 C10 C15 70.3(3) . . . . ? N1 C10 C11 C12 53.1(3) . . . . ? C16 C10 C11 C12 170.7(2) . . . . ? C15 C10 C11 C12 -73.0(3) . . . . ? C10 C11 C12 C13 -58.1(3) . . . . ? C11 C12 C13 C14 57.8(3) . . . . ? C3 N1 C14 C13 -160.16(19) . . . . ? C10 N1 C14 C13 52.3(3) . . . . ? C3 N1 C14 C17 75.9(3) . . . . ? C10 N1 C14 C17 -71.6(3) . . . . ? C3 N1 C14 C18 -43.9(3) . . . . ? C10 N1 C14 C18 168.6(2) . . . . ? C12 C13 C14 N1 -52.4(3) . . . . ? C12 C13 C14 C17 75.2(3) . . . . ? C12 C13 C14 C18 -168.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.444 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.068 #===END