# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 # Electronic Su_publ_co ntact_author_name 'Yoshitane Imai' _publ_contact_author_address ; Kinki University Higashi-osaka 577-8502 JAPAN ; _publ_contact_author_email Y-IMAI@APCH.KINDAI.AC.JP _publ_section_title ; Multiple Molecular Response Columnar Host System Composed of Rac-2-Amino-1,2-diphenylethanol and 1-Fluorenecarboxylic Acid ; loop_ _publ_author_name 'Yoshitane Imai' 'Michiya Fujiki' 'Takunori Harada' 'Kakuhiro Kawaguchi' 'Reiko Kuroda' 'Yoshio Matsubara' ; K.Murata ; 'Keiko Nagasaki' 'Yoko Nakano' 'Tomohiro Sato' data_imai82_1 _database_code_depnum_ccdc_archive 'CCDC 678709' #data_im6375a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H31 N O4' _chemical_formula_weight 469.56 _chemical_absolute_configuration rm 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 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' _cell_length_a 28.581(2) _cell_length_b 6.1600(5) _cell_length_c 14.2146(11) _cell_angle_alpha 90.00 _cell_angle_beta 97.4410(10) _cell_angle_gamma 90.00 _cell_volume 2481.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5132 _cell_measurement_theta_min 1.44 _cell_measurement_theta_max 27.88 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9676 _exptl_absorpt_correction_T_max 0.9877 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11038 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 27.88 _reflns_number_total 5573 _reflns_number_gt 5132 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0647P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.7(9) _refine_ls_number_reflns 5573 _refine_ls_number_parameters 328 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1146 _refine_ls_wR_factor_gt 0.1016 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _refine_ls_shift/su_max 0.005 _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 C1 C 0.12723(6) 0.7633(3) 0.10446(12) 0.0188(4) Uani 1 1 d . . . C2 C 0.10835(7) 0.9549(3) 0.06403(15) 0.0283(4) Uani 1 1 d . . . H2 H 0.1239 1.0277 0.0180 0.034 Uiso 1 1 calc R . . C3 C 0.06692(8) 1.0413(4) 0.09023(17) 0.0360(5) Uani 1 1 d . . . H3 H 0.0538 1.1690 0.0599 0.043 Uiso 1 1 calc R . . C4 C 0.04468(7) 0.9440(3) 0.15963(15) 0.0298(4) Uani 1 1 d . . . H4 H 0.0167 1.0046 0.1779 0.036 Uiso 1 1 calc R . . C5 C 0.06384(6) 0.7572(3) 0.20203(13) 0.0215(4) Uani 1 1 d . . . C6 C 0.10476(6) 0.6641(3) 0.17407(12) 0.0178(4) Uani 1 1 d . . . C7 C 0.06697(7) 0.2694(4) 0.34693(13) 0.0287(4) Uani 1 1 d . . . H7 H 0.0872 0.1469 0.3566 0.034 Uiso 1 1 calc R . . C8 C 0.02641(7) 0.2837(4) 0.39181(14) 0.0305(5) Uani 1 1 d . . . H8 H 0.0188 0.1688 0.4317 0.037 Uiso 1 1 calc R . . C9 C -0.00279(7) 0.4631(4) 0.37884(13) 0.0294(5) Uani 1 1 d . . . H9 H -0.0299 0.4710 0.4110 0.035 Uiso 1 1 calc R . . C10 C 0.00684(6) 0.6308(4) 0.31993(13) 0.0252(4) Uani 1 1 d . . . H10 H -0.0133 0.7537 0.3111 0.030 Uiso 1 1 calc R . . C11 C 0.04689(6) 0.6156(3) 0.27356(12) 0.0210(4) Uani 1 1 d . . . C12 C 0.07698(6) 0.4371(3) 0.28829(12) 0.0219(4) Uani 1 1 d . . . C13 C 0.11712(6) 0.4585(3) 0.22931(13) 0.0218(4) Uani 1 1 d . . . C14 C 0.16905(6) 0.6615(3) 0.06663(12) 0.0184(4) Uani 1 1 d . . . O15 O 0.16721(4) 0.4594(2) 0.05298(8) 0.0192(3) Uani 1 1 d . . . O16 O 0.20203(4) 0.7822(2) 0.04827(9) 0.0242(3) Uani 1 1 d . . . C21 C 0.15321(6) 0.7062(3) 0.70547(13) 0.0193(4) Uani 1 1 d . . . C22 C 0.15041(7) 0.5764(3) 0.62520(14) 0.0258(4) Uani 1 1 d . . . H22 H 0.1674 0.4436 0.6271 0.031 Uiso 1 1 calc R . . C23 C 0.12291(7) 0.6395(4) 0.54223(14) 0.0316(5) Uani 1 1 d . . . H23 H 0.1210 0.5494 0.4876 0.038 Uiso 1 1 calc R . . C24 C 0.09837(7) 0.8328(4) 0.53862(15) 0.0326(5) Uani 1 1 d . . . H24 H 0.0796 0.8758 0.4816 0.039 Uiso 1 1 calc R . . C25 C 0.10110(7) 0.9633(4) 0.61778(15) 0.0328(5) Uani 1 1 d . . . H25 H 0.0843 1.0967 0.6153 0.039 Uiso 1 1 calc R . . C26 C 0.12845(6) 0.8998(3) 0.70130(14) 0.0254(4) Uani 1 1 d . . . H26 H 0.1301 0.9899 0.7559 0.031 Uiso 1 1 calc R . . C27 C 0.18348(6) 0.6407(3) 0.79626(13) 0.0195(4) Uani 1 1 d . . . H27 H 0.1658 0.6748 0.8508 0.023 Uiso 1 1 calc R . . O28 O 0.19495(4) 0.4166(2) 0.79971(9) 0.0236(3) Uani 1 1 d . . . H28 H 0.1732 0.3467 0.8206 0.035 Uiso 1 1 calc R . . C29 C 0.25948(6) 0.7357(3) 0.72933(12) 0.0189(4) Uani 1 1 d . . . C30 C 0.25786(6) 0.8954(3) 0.65964(13) 0.0230(4) Uani 1 1 d . . . H30 H 0.2405 1.0250 0.6659 0.028 Uiso 1 1 calc R . . C31 C 0.28135(7) 0.8666(4) 0.58119(14) 0.0290(5) Uani 1 1 d . . . H31 H 0.2800 0.9763 0.5339 0.035 Uiso 1 1 calc R . . C32 C 0.30677(7) 0.6786(4) 0.57141(14) 0.0290(5) Uani 1 1 d . . . H32 H 0.3227 0.6589 0.5174 0.035 Uiso 1 1 calc R . . C33 C 0.30897(7) 0.5194(4) 0.64058(14) 0.0273(4) Uani 1 1 d . . . H33 H 0.3268 0.3911 0.6344 0.033 Uiso 1 1 calc R . . C34 C 0.28519(6) 0.5469(3) 0.71898(13) 0.0221(4) Uani 1 1 d . . . H34 H 0.2865 0.4363 0.7658 0.026 Uiso 1 1 calc R . . C35 C 0.23060(6) 0.7658(3) 0.81030(12) 0.0173(3) Uani 1 1 d . . . H35 H 0.2232 0.9239 0.8147 0.021 Uiso 1 1 calc R . . N36 N 0.25710(5) 0.6971(2) 0.90300(10) 0.0180(3) Uani 1 1 d . . . H36A H 0.2661 0.5560 0.8992 0.027 Uiso 1 1 calc R . . H36B H 0.2382 0.7111 0.9495 0.027 Uiso 1 1 calc R . . H36C H 0.2831 0.7822 0.9168 0.027 Uiso 1 1 calc R . . O41 O 0.12182(5) 1.2924(2) 0.88724(10) 0.0279(3) Uani 1 1 d . . . H41 H 0.1301 1.3437 0.9416 0.042 Uiso 1 1 calc R . . C42 C 0.07220(8) 1.3147(4) 0.86395(16) 0.0398(6) Uani 1 1 d . . . H42A H 0.0565 1.1870 0.8883 0.048 Uiso 1 1 calc R . . H42B H 0.0643 1.3168 0.7941 0.048 Uiso 1 1 calc R . . C43 C 0.05338(9) 1.5174(5) 0.90432(17) 0.0482(7) Uani 1 1 d . . . H43A H 0.0607 1.5154 0.9736 0.072 Uiso 1 1 calc R . . H43B H 0.0191 1.5243 0.8867 0.072 Uiso 1 1 calc R . . H43C H 0.0681 1.6448 0.8790 0.072 Uiso 1 1 calc R . . H13A H 0.1471(7) 0.474(4) 0.2737(14) 0.022(5) Uiso 1 1 d . . . H13B H 0.1182(7) 0.334(4) 0.1892(16) 0.031(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 C1 0.0154(8) 0.0184(8) 0.0219(9) -0.0019(7) 0.0001(7) -0.0007(7) C2 0.0289(10) 0.0200(9) 0.0376(11) 0.0057(8) 0.0100(8) 0.0004(8) C3 0.0330(12) 0.0235(10) 0.0529(14) 0.0125(10) 0.0102(10) 0.0120(9) C4 0.0242(10) 0.0266(11) 0.0402(11) 0.0010(9) 0.0099(8) 0.0084(9) C5 0.0175(8) 0.0248(9) 0.0219(9) -0.0037(8) 0.0022(7) 0.0007(7) C6 0.0154(8) 0.0186(9) 0.0189(8) -0.0024(7) -0.0004(7) 0.0004(7) C7 0.0267(10) 0.0371(11) 0.0234(9) 0.0069(9) 0.0074(8) 0.0062(9) C8 0.0291(10) 0.0433(12) 0.0206(9) 0.0048(9) 0.0097(8) -0.0015(10) C9 0.0204(9) 0.0489(13) 0.0201(9) -0.0061(9) 0.0075(7) -0.0016(9) C10 0.0193(9) 0.0345(11) 0.0220(9) -0.0055(8) 0.0035(7) 0.0030(8) C11 0.0174(8) 0.0273(10) 0.0179(9) -0.0063(7) 0.0012(7) 0.0003(7) C12 0.0189(8) 0.0324(11) 0.0146(8) -0.0004(8) 0.0029(6) 0.0020(8) C13 0.0190(9) 0.0269(10) 0.0203(9) 0.0050(8) 0.0058(7) 0.0052(8) C14 0.0184(9) 0.0221(10) 0.0143(8) 0.0003(7) 0.0007(6) -0.0002(7) O15 0.0182(6) 0.0189(6) 0.0205(6) -0.0008(5) 0.0021(5) 0.0013(5) O16 0.0237(7) 0.0261(7) 0.0248(7) -0.0040(6) 0.0112(5) -0.0067(6) C21 0.0124(8) 0.0235(9) 0.0226(9) 0.0001(7) 0.0047(7) -0.0045(7) C22 0.0235(9) 0.0285(11) 0.0261(10) -0.0033(8) 0.0058(8) -0.0014(8) C23 0.0287(10) 0.0432(12) 0.0228(10) -0.0021(9) 0.0028(8) -0.0078(10) C24 0.0252(10) 0.0426(13) 0.0280(11) 0.0104(9) -0.0042(8) -0.0083(9) C25 0.0233(10) 0.0292(11) 0.0447(12) 0.0077(10) -0.0003(9) 0.0029(9) C26 0.0207(9) 0.0233(10) 0.0320(10) -0.0035(8) 0.0020(8) -0.0004(7) C27 0.0184(9) 0.0202(9) 0.0209(9) 0.0001(7) 0.0058(7) -0.0021(7) O28 0.0217(7) 0.0194(7) 0.0301(7) 0.0015(6) 0.0050(5) -0.0036(5) C29 0.0137(8) 0.0239(10) 0.0191(8) -0.0002(7) 0.0027(6) -0.0048(7) C30 0.0171(9) 0.0269(10) 0.0247(10) 0.0061(8) 0.0016(7) -0.0014(7) C31 0.0219(10) 0.0445(12) 0.0199(10) 0.0105(9) 0.0006(7) -0.0044(9) C32 0.0236(10) 0.0456(13) 0.0183(9) -0.0008(9) 0.0054(7) -0.0060(9) C33 0.0233(10) 0.0314(11) 0.0281(10) -0.0071(8) 0.0064(8) -0.0027(8) C34 0.0216(9) 0.0233(9) 0.0217(9) 0.0020(7) 0.0046(7) -0.0039(8) C35 0.0159(8) 0.0168(8) 0.0191(8) 0.0017(7) 0.0026(6) -0.0005(7) N36 0.0179(7) 0.0177(7) 0.0191(7) 0.0009(6) 0.0048(6) -0.0022(6) O41 0.0283(7) 0.0322(8) 0.0232(7) -0.0001(6) 0.0030(5) -0.0110(6) C42 0.0324(12) 0.0558(16) 0.0286(11) -0.0050(10) -0.0065(9) -0.0018(11) C43 0.0447(14) 0.0623(17) 0.0345(13) -0.0003(12) -0.0071(10) 0.0130(13) _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 C6 1.389(2) . ? C1 C2 1.391(3) . ? C1 C14 1.509(2) . ? C2 C3 1.392(3) . ? C3 C4 1.378(3) . ? C4 C5 1.379(3) . ? C5 C6 1.405(3) . ? C5 C11 1.469(3) . ? C6 C13 1.508(3) . ? C7 C12 1.380(3) . ? C7 C8 1.396(3) . ? C8 C9 1.383(3) . ? C9 C10 1.380(3) . ? C10 C11 1.396(3) . ? C11 C12 1.395(3) . ? C12 C13 1.512(2) . ? C14 O16 1.254(2) . ? C14 O15 1.260(2) . ? C21 C26 1.384(3) . ? C21 C22 1.387(3) . ? C21 C27 1.513(3) . ? C22 C23 1.386(3) . ? C23 C24 1.379(3) . ? C24 C25 1.377(3) . ? C25 C26 1.390(3) . ? C27 O28 1.418(2) . ? C27 C35 1.542(2) . ? C29 C30 1.392(3) . ? C29 C34 1.394(3) . ? C29 C35 1.512(2) . ? C30 C31 1.385(3) . ? C31 C32 1.383(3) . ? C32 C33 1.384(3) . ? C33 C34 1.389(3) . ? C35 N36 1.493(2) . ? O41 C42 1.421(3) . ? C42 C43 1.503(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 118.53(17) . . ? C6 C1 C14 122.09(16) . . ? C2 C1 C14 119.23(16) . . ? C1 C2 C3 120.77(19) . . ? C4 C3 C2 120.83(19) . . ? C3 C4 C5 118.82(18) . . ? C4 C5 C6 120.99(18) . . ? C4 C5 C11 130.57(17) . . ? C6 C5 C11 108.33(17) . . ? C1 C6 C5 120.01(17) . . ? C1 C6 C13 129.94(16) . . ? C5 C6 C13 110.05(16) . . ? C12 C7 C8 118.6(2) . . ? C9 C8 C7 120.8(2) . . ? C10 C9 C8 120.99(17) . . ? C9 C10 C11 118.46(19) . . ? C12 C11 C10 120.62(18) . . ? C12 C11 C5 108.66(15) . . ? C10 C11 C5 130.62(18) . . ? C7 C12 C11 120.56(16) . . ? C7 C12 C13 129.19(18) . . ? C11 C12 C13 110.20(16) . . ? C6 C13 C12 102.64(15) . . ? O16 C14 O15 124.83(17) . . ? O16 C14 C1 118.61(16) . . ? O15 C14 C1 116.51(16) . . ? C26 C21 C22 119.14(17) . . ? C26 C21 C27 119.95(17) . . ? C22 C21 C27 120.90(17) . . ? C23 C22 C21 120.3(2) . . ? C24 C23 C22 120.2(2) . . ? C25 C24 C23 119.92(19) . . ? C24 C25 C26 120.0(2) . . ? C21 C26 C25 120.45(19) . . ? O28 C27 C21 113.16(15) . . ? O28 C27 C35 106.72(14) . . ? C21 C27 C35 111.76(14) . . ? C30 C29 C34 118.93(16) . . ? C30 C29 C35 118.94(17) . . ? C34 C29 C35 121.99(16) . . ? C31 C30 C29 120.48(19) . . ? C32 C31 C30 120.24(19) . . ? C31 C32 C33 119.84(18) . . ? C32 C33 C34 120.1(2) . . ? C33 C34 C29 120.39(18) . . ? N36 C35 C29 111.86(14) . . ? N36 C35 C27 107.90(14) . . ? C29 C35 C27 113.21(14) . . ? O41 C42 C43 112.8(2) . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.264 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.059 #==END data_imai82_2 _database_code_depnum_ccdc_archive 'CCDC 678710' #data_im7623a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H33 N O4' _chemical_formula_weight 483.58 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.9729(15) _cell_length_b 6.1709(7) _cell_length_c 29.952(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.452(2) _cell_angle_gamma 90.00 _cell_volume 2574.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 3968 _cell_measurement_theta_min 1.36 _cell_measurement_theta_max 27.89 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9641 _exptl_absorpt_correction_T_max 0.9919 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14902 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_sigmaI/netI 0.0729 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 27.89 _reflns_number_total 5835 _reflns_number_gt 3968 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0721P)^2^+0.3262P] 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 5835 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1083 _refine_ls_R_factor_gt 0.0662 _refine_ls_wR_factor_ref 0.1632 _refine_ls_wR_factor_gt 0.1398 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _refine_ls_shift/su_max 0.002 _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 0.00851(18) 0.7365(4) 0.05232(8) 0.0274(6) Uani 1 1 d . . . H1 H -0.0210 0.8026 0.0261 0.033 Uiso 1 1 calc R . . C2 C 0.08971(18) 0.8265(4) 0.07440(9) 0.0299(6) Uani 1 1 d . . . H2 H 0.1165 0.9550 0.0631 0.036 Uiso 1 1 calc R . . C3 C 0.13242(17) 0.7310(4) 0.11288(8) 0.0239(5) Uani 1 1 d . . . H3 H 0.1872 0.7974 0.1279 0.029 Uiso 1 1 calc R . . C4 C 0.09663(15) 0.5395(4) 0.12999(7) 0.0173(5) Uani 1 1 d . . . C5 C 0.01496(15) 0.4467(4) 0.10753(7) 0.0184(5) Uani 1 1 d . . . C6 C -0.02911(16) 0.5474(4) 0.06924(8) 0.0209(5) Uani 1 1 d . . . C7 C -0.17796(18) 0.4432(5) 0.01603(9) 0.0342(7) Uani 1 1 d . . . H7 H -0.1746 0.5665 -0.0028 0.041 Uiso 1 1 calc R . . C8 C -0.24808(18) 0.2878(5) 0.00723(10) 0.0396(7) Uani 1 1 d . . . H8 H -0.2936 0.3051 -0.0178 0.047 Uiso 1 1 calc R . . C9 C -0.25275(18) 0.1076(5) 0.03437(9) 0.0363(7) Uani 1 1 d . . . H9 H -0.3010 0.0016 0.0276 0.044 Uiso 1 1 calc R . . C10 C -0.18756(17) 0.0793(5) 0.07160(9) 0.0316(6) Uani 1 1 d . . . H10 H -0.1909 -0.0448 0.0902 0.038 Uiso 1 1 calc R . . C11 C -0.11788(16) 0.2362(4) 0.08088(8) 0.0237(5) Uani 1 1 d . . . C12 C -0.11237(16) 0.4157(4) 0.05294(8) 0.0235(5) Uani 1 1 d . . . C13 C -0.03942(16) 0.2449(4) 0.11849(8) 0.0208(5) Uani 1 1 d . . . H13A H -0.0665 0.2575 0.1480 0.025 Uiso 1 1 calc R . . H13B H 0.0022 0.1150 0.1185 0.025 Uiso 1 1 calc R . . C14 C 0.14806(14) 0.4349(4) 0.16994(8) 0.0178(5) Uani 1 1 d . . . O15 O 0.15947(11) 0.2314(3) 0.16835(5) 0.0211(4) Uani 1 1 d . . . O16 O 0.17913(11) 0.5508(3) 0.20243(5) 0.0248(4) Uani 1 1 d . . . C21 C 0.50325(15) 0.4794(4) 0.16118(7) 0.0180(5) Uani 1 1 d . . . C22 C 0.58194(16) 0.3433(4) 0.16051(8) 0.0243(6) Uani 1 1 d . . . H22 H 0.5842 0.2140 0.1778 0.029 Uiso 1 1 calc R . . C23 C 0.65732(17) 0.3938(4) 0.13491(8) 0.0278(6) Uani 1 1 d . . . H23 H 0.7105 0.2980 0.1344 0.033 Uiso 1 1 calc R . . C24 C 0.65550(17) 0.5827(4) 0.11015(8) 0.0269(6) Uani 1 1 d . . . H24 H 0.7072 0.6169 0.0926 0.032 Uiso 1 1 calc R . . C25 C 0.57816(18) 0.7218(4) 0.11102(9) 0.0302(6) Uani 1 1 d . . . H25 H 0.5771 0.8531 0.0944 0.036 Uiso 1 1 calc R . . C26 C 0.50189(17) 0.6694(4) 0.13623(8) 0.0238(5) Uani 1 1 d . . . H26 H 0.4484 0.7643 0.1364 0.029 Uiso 1 1 calc R . . C27 C 0.42032(16) 0.4228(4) 0.18886(8) 0.0194(5) Uani 1 1 d . . . H27 H 0.3594 0.4682 0.1717 0.023 Uiso 1 1 calc R . . O28 O 0.41425(12) 0.1975(3) 0.19796(5) 0.0243(4) Uani 1 1 d . . . H28 H 0.3861 0.1344 0.1758 0.036 Uiso 1 1 calc R . . C29 C 0.52249(15) 0.5053(4) 0.26106(7) 0.0179(5) Uani 1 1 d . . . C30 C 0.59313(16) 0.6622(4) 0.25909(8) 0.0231(5) Uani 1 1 d . . . H30 H 0.5796 0.7924 0.2429 0.028 Uiso 1 1 calc R . . C31 C 0.68399(17) 0.6291(4) 0.28083(8) 0.0278(6) Uani 1 1 d . . . H31 H 0.7324 0.7363 0.2791 0.033 Uiso 1 1 calc R . . C32 C 0.70382(16) 0.4412(4) 0.30487(8) 0.0270(6) Uani 1 1 d . . . H32 H 0.7656 0.4192 0.3197 0.032 Uiso 1 1 calc R . . C33 C 0.63301(16) 0.2849(4) 0.30715(8) 0.0269(6) Uani 1 1 d . . . H33 H 0.6462 0.1557 0.3238 0.032 Uiso 1 1 calc R . . C34 C 0.54269(16) 0.3167(4) 0.28515(8) 0.0233(5) Uani 1 1 d . . . H34 H 0.4946 0.2086 0.2866 0.028 Uiso 1 1 calc R . . C35 C 0.42705(15) 0.5410(4) 0.23400(7) 0.0182(5) Uani 1 1 d . . . H35 H 0.4203 0.6998 0.2279 0.022 Uiso 1 1 calc R . . N36 N 0.34386(12) 0.4717(3) 0.25920(6) 0.0176(4) Uani 1 1 d . . . H36A H 0.3530 0.3328 0.2688 0.026 Uiso 1 1 calc R . . H36B H 0.2888 0.4799 0.2409 0.026 Uiso 1 1 calc R . . H36C H 0.3392 0.5603 0.2832 0.026 Uiso 1 1 calc R . . O41 O -0.30485(11) -0.0932(3) -0.11998(5) 0.0249(4) Uani 1 1 d . . . H41 H -0.2544 -0.1376 -0.1305 0.037 Uiso 1 1 calc R . . C42 C -0.32318(17) -0.2190(4) -0.08127(8) 0.0255(6) Uani 1 1 d . . . H42A H -0.2701 -0.2005 -0.0577 0.031 Uiso 1 1 calc R . . H42B H -0.3278 -0.3745 -0.0892 0.031 Uiso 1 1 calc R . . C43 C -0.41595(17) -0.1428(4) -0.06435(8) 0.0262(6) Uani 1 1 d . . . H43A H -0.4661 -0.1398 -0.0896 0.031 Uiso 1 1 calc R . . H43B H -0.4075 0.0069 -0.0528 0.031 Uiso 1 1 calc R . . C44 C -0.4494(2) -0.2868(5) -0.02740(9) 0.0379(7) Uani 1 1 d . . . H44A H -0.4628 -0.4326 -0.0393 0.057 Uiso 1 1 calc R . . H44B H -0.5078 -0.2259 -0.0163 0.057 Uiso 1 1 calc R . . H44C H -0.3990 -0.2946 -0.0028 0.057 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 C1 0.0335(14) 0.0241(14) 0.0244(13) 0.0048(11) 0.0004(11) 0.0058(11) C2 0.0379(15) 0.0202(14) 0.0321(15) 0.0052(11) 0.0067(12) -0.0030(11) C3 0.0241(12) 0.0184(13) 0.0294(13) -0.0027(11) 0.0040(10) -0.0045(10) C4 0.0159(11) 0.0148(12) 0.0216(12) -0.0024(9) 0.0039(9) 0.0030(9) C5 0.0186(11) 0.0161(12) 0.0210(12) -0.0006(10) 0.0054(9) 0.0030(9) C6 0.0180(11) 0.0237(14) 0.0210(12) -0.0027(10) 0.0018(9) 0.0045(10) C7 0.0287(14) 0.0426(18) 0.0301(14) -0.0026(13) -0.0048(11) 0.0068(13) C8 0.0245(13) 0.058(2) 0.0345(16) -0.0136(15) -0.0081(12) 0.0043(14) C9 0.0203(13) 0.053(2) 0.0354(16) -0.0161(14) 0.0010(11) -0.0069(13) C10 0.0229(13) 0.0375(17) 0.0347(15) -0.0076(12) 0.0046(11) -0.0066(12) C11 0.0163(11) 0.0309(15) 0.0242(13) -0.0070(11) 0.0030(10) 0.0012(10) C12 0.0182(11) 0.0292(14) 0.0230(13) -0.0073(11) 0.0017(10) 0.0051(10) C13 0.0185(11) 0.0217(13) 0.0219(12) -0.0011(10) -0.0004(9) -0.0053(10) C14 0.0111(10) 0.0185(13) 0.0244(12) -0.0022(10) 0.0046(9) -0.0005(9) O15 0.0211(8) 0.0182(9) 0.0239(9) 0.0024(7) 0.0006(7) 0.0005(7) O16 0.0195(8) 0.0259(10) 0.0277(9) -0.0091(8) -0.0055(7) 0.0056(7) C21 0.0180(11) 0.0194(13) 0.0163(11) -0.0042(9) -0.0012(9) -0.0011(9) C22 0.0213(12) 0.0262(14) 0.0251(13) 0.0020(11) 0.0000(10) 0.0032(10) C23 0.0194(12) 0.0344(15) 0.0295(14) -0.0048(12) 0.0015(11) 0.0055(11) C24 0.0195(12) 0.0359(16) 0.0261(14) -0.0009(11) 0.0064(10) -0.0020(11) C25 0.0318(14) 0.0295(15) 0.0300(14) 0.0052(12) 0.0068(11) 0.0000(12) C26 0.0212(12) 0.0242(14) 0.0265(13) 0.0003(11) 0.0048(10) 0.0044(10) C27 0.0200(11) 0.0167(13) 0.0211(12) 0.0000(10) -0.0013(9) -0.0010(9) O28 0.0292(9) 0.0181(9) 0.0251(9) -0.0034(7) -0.0005(7) -0.0040(7) C29 0.0179(11) 0.0196(13) 0.0166(11) -0.0056(9) 0.0025(9) -0.0029(9) C30 0.0227(12) 0.0264(14) 0.0205(12) 0.0008(10) 0.0030(10) -0.0027(10) C31 0.0202(12) 0.0390(16) 0.0237(13) -0.0023(12) -0.0009(10) -0.0096(11) C32 0.0162(11) 0.0415(17) 0.0229(13) -0.0046(12) -0.0005(10) 0.0008(11) C33 0.0223(12) 0.0277(15) 0.0305(14) 0.0027(11) 0.0006(11) 0.0035(11) C34 0.0184(11) 0.0248(14) 0.0264(13) 0.0013(11) -0.0005(10) -0.0033(10) C35 0.0153(10) 0.0176(12) 0.0215(12) 0.0015(10) 0.0011(9) -0.0033(9) N36 0.0140(9) 0.0192(11) 0.0192(10) -0.0036(8) -0.0004(8) -0.0001(8) O41 0.0229(9) 0.0254(10) 0.0272(9) -0.0005(8) 0.0064(7) -0.0026(7) C42 0.0256(12) 0.0259(14) 0.0246(13) 0.0012(11) -0.0001(11) -0.0027(11) C43 0.0236(12) 0.0312(15) 0.0239(13) -0.0028(11) 0.0020(10) -0.0025(11) C44 0.0366(15) 0.0453(19) 0.0329(15) -0.0020(13) 0.0097(13) -0.0107(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.384(3) . ? C1 C6 1.392(3) . ? C2 C3 1.388(3) . ? C3 C4 1.396(3) . ? C4 C5 1.401(3) . ? C4 C14 1.494(3) . ? C5 C6 1.404(3) . ? C5 C13 1.508(3) . ? C6 C12 1.471(3) . ? C7 C8 1.382(4) . ? C7 C12 1.390(3) . ? C8 C9 1.382(4) . ? C9 C10 1.395(4) . ? C10 C11 1.386(3) . ? C11 C12 1.394(4) . ? C11 C13 1.511(3) . ? C14 O16 1.257(3) . ? C14 O15 1.267(3) . ? C21 C22 1.385(3) . ? C21 C26 1.390(3) . ? C21 C27 1.517(3) . ? C22 C23 1.386(3) . ? C23 C24 1.381(4) . ? C24 C25 1.382(3) . ? C25 C26 1.391(3) . ? C27 O28 1.421(3) . ? C27 C35 1.533(3) . ? C29 C30 1.387(3) . ? C29 C34 1.387(3) . ? C29 C35 1.522(3) . ? C30 C31 1.396(3) . ? C31 C32 1.381(4) . ? C32 C33 1.388(3) . ? C33 C34 1.391(3) . ? C35 N36 1.497(3) . ? O41 C42 1.435(3) . ? C42 C43 1.503(3) . ? C43 C44 1.520(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 118.8(2) . . ? C1 C2 C3 120.7(2) . . ? C2 C3 C4 121.4(2) . . ? C3 C4 C5 118.1(2) . . ? C3 C4 C14 119.7(2) . . ? C5 C4 C14 122.1(2) . . ? C4 C5 C6 120.0(2) . . ? C4 C5 C13 129.6(2) . . ? C6 C5 C13 110.29(19) . . ? C1 C6 C5 121.0(2) . . ? C1 C6 C12 130.8(2) . . ? C5 C6 C12 108.2(2) . . ? C8 C7 C12 118.7(3) . . ? C7 C8 C9 120.8(2) . . ? C8 C9 C10 120.9(3) . . ? C11 C10 C9 118.5(3) . . ? C10 C11 C12 120.4(2) . . ? C10 C11 C13 129.2(2) . . ? C12 C11 C13 110.4(2) . . ? C7 C12 C11 120.7(2) . . ? C7 C12 C6 130.7(2) . . ? C11 C12 C6 108.6(2) . . ? C5 C13 C11 102.45(19) . . ? O16 C14 O15 123.8(2) . . ? O16 C14 C4 119.3(2) . . ? O15 C14 C4 116.9(2) . . ? C22 C21 C26 118.8(2) . . ? C22 C21 C27 120.6(2) . . ? C26 C21 C27 120.6(2) . . ? C21 C22 C23 120.7(2) . . ? C24 C23 C22 120.3(2) . . ? C23 C24 C25 119.7(2) . . ? C24 C25 C26 119.9(2) . . ? C21 C26 C25 120.6(2) . . ? O28 C27 C21 112.94(19) . . ? O28 C27 C35 107.29(18) . . ? C21 C27 C35 112.04(18) . . ? C30 C29 C34 119.4(2) . . ? C30 C29 C35 118.3(2) . . ? C34 C29 C35 122.2(2) . . ? C29 C30 C31 120.2(2) . . ? C32 C31 C30 120.3(2) . . ? C31 C32 C33 119.6(2) . . ? C32 C33 C34 120.2(2) . . ? C29 C34 C33 120.3(2) . . ? N36 C35 C29 111.89(17) . . ? N36 C35 C27 108.18(17) . . ? C29 C35 C27 113.08(18) . . ? O41 C42 C43 108.4(2) . . ? C42 C43 C44 112.6(2) . . ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 27.89 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.326 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.090 #==END data_imai82_3 _database_code_depnum_ccdc_archive 'CCDC 678711' #data_im7647a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H35 N O4' _chemical_formula_weight 497.61 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.4950(13) _cell_length_b 6.2388(5) _cell_length_c 26.400(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.2010(10) _cell_angle_gamma 90.00 _cell_volume 2633.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4610 _cell_measurement_theta_min 1.33 _cell_measurement_theta_max 27.93 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9602 _exptl_absorpt_correction_T_max 0.9919 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15731 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_sigmaI/netI 0.0413 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 27.93 _reflns_number_total 5973 _reflns_number_gt 4610 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0493P)^2^+3.8395P] 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 5973 _refine_ls_number_parameters 338 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0885 _refine_ls_R_factor_gt 0.0692 _refine_ls_wR_factor_ref 0.1606 _refine_ls_wR_factor_gt 0.1487 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.003 _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 0.91613(19) -0.3522(7) 0.0153(2) 0.104(2) Uani 1 1 d . . . H1 H 0.9720 -0.3894 0.0153 0.125 Uiso 1 1 calc R . . C2 C 0.85039(19) -0.4784(7) -0.0107(2) 0.0978(19) Uani 1 1 d . . . H2 H 0.8612 -0.6026 -0.0288 0.117 Uiso 1 1 calc R . . C3 C 0.76939(16) -0.4266(5) -0.01068(12) 0.0432(7) Uani 1 1 d . . . H3 H 0.7249 -0.5175 -0.0279 0.052 Uiso 1 1 calc R . . C4 C 0.75211(13) -0.2432(3) 0.01416(8) 0.0205(4) Uani 1 1 d . . . C5 C 0.81890(13) -0.1154(3) 0.04047(8) 0.0201(4) Uani 1 1 d . . . C6 C 0.90027(15) -0.1736(4) 0.04089(11) 0.0368(6) Uani 1 1 d . . . C7 C 1.04404(18) -0.0042(6) 0.08325(17) 0.0725(13) Uani 1 1 d . . . H7 H 1.0758 -0.1116 0.0714 0.087 Uiso 1 1 calc R . . C8 C 1.08363(16) 0.1661(5) 0.11251(13) 0.0497(8) Uani 1 1 d . . . H8 H 1.1429 0.1756 0.1208 0.060 Uiso 1 1 calc R . . C9 C 1.03869(15) 0.3199(4) 0.12950(9) 0.0341(6) Uani 1 1 d . . . H9 H 1.0666 0.4364 0.1496 0.041 Uiso 1 1 calc R . . C10 C 0.95260(17) 0.3079(5) 0.11774(12) 0.0488(8) Uani 1 1 d . . . H10 H 0.9212 0.4170 0.1294 0.059 Uiso 1 1 calc R . . C11 C 0.91217(14) 0.1375(4) 0.08906(9) 0.0285(5) Uani 1 1 d . . . C12 C 0.95806(14) -0.0167(4) 0.07145(10) 0.0305(5) Uani 1 1 d . . . C13 C 0.81998(15) 0.0869(5) 0.07112(12) 0.0404(7) Uani 1 1 d . . . H13A H 0.7951 0.0642 0.1012 0.049 Uiso 1 1 calc R . . H13B H 0.7893 0.2032 0.0489 0.049 Uiso 1 1 calc R . . C14 C 0.66260(13) -0.1839(4) 0.00984(8) 0.0205(4) Uani 1 1 d . . . O15 O 0.64494(10) 0.0130(3) 0.00558(6) 0.0280(4) Uani 1 1 d . . . O16 O 0.61041(9) -0.3303(3) 0.00848(6) 0.0270(4) Uani 1 1 d . . . C21 C 0.49494(12) 0.3418(4) 0.17765(8) 0.0203(4) Uani 1 1 d . . . C22 C 0.47277(13) 0.1444(4) 0.19381(9) 0.0232(5) Uani 1 1 d . . . H22 H 0.4548 0.0337 0.1689 0.028 Uiso 1 1 calc R . . C23 C 0.47642(14) 0.1061(4) 0.24602(9) 0.0267(5) Uani 1 1 d . . . H23 H 0.4612 -0.0303 0.2568 0.032 Uiso 1 1 calc R . . C24 C 0.50216(14) 0.2667(4) 0.28236(9) 0.0291(5) Uani 1 1 d . . . H24 H 0.5046 0.2413 0.3182 0.035 Uiso 1 1 calc R . . C25 C 0.52436(15) 0.4640(4) 0.26656(9) 0.0318(5) Uani 1 1 d . . . H25 H 0.5421 0.5746 0.2916 0.038 Uiso 1 1 calc R . . C26 C 0.52090(14) 0.5020(4) 0.21439(9) 0.0274(5) Uani 1 1 d . . . H26 H 0.5364 0.6384 0.2038 0.033 Uiso 1 1 calc R . . C27 C 0.49135(13) 0.3791(4) 0.12046(8) 0.0211(4) Uani 1 1 d . . . H27 H 0.4353 0.3317 0.0993 0.025 Uiso 1 1 calc R . . O28 O 0.50329(10) 0.5955(3) 0.10833(6) 0.0271(4) Uani 1 1 d . . . H28 H 0.4577 0.6615 0.1036 0.041 Uiso 1 1 calc R . . C29 C 0.64668(13) 0.2876(4) 0.13657(8) 0.0211(4) Uani 1 1 d . . . C30 C 0.68581(14) 0.1314(4) 0.17156(9) 0.0283(5) Uani 1 1 d . . . H30 H 0.6584 -0.0012 0.1735 0.034 Uiso 1 1 calc R . . C31 C 0.76482(14) 0.1677(5) 0.20378(9) 0.0340(6) Uani 1 1 d . . . H31 H 0.7911 0.0604 0.2278 0.041 Uiso 1 1 calc R . . C32 C 0.80494(14) 0.3589(4) 0.20100(9) 0.0307(5) Uani 1 1 d . . . H32 H 0.8590 0.3835 0.2231 0.037 Uiso 1 1 calc R . . C33 C 0.76691(14) 0.5153(4) 0.16623(9) 0.0284(5) Uani 1 1 d . . . H33 H 0.7949 0.6470 0.1643 0.034 Uiso 1 1 calc R . . C34 C 0.68786(13) 0.4801(4) 0.13409(9) 0.0240(5) Uani 1 1 d . . . H34 H 0.6618 0.5881 0.1103 0.029 Uiso 1 1 calc R . . C35 C 0.55918(13) 0.2463(4) 0.10371(8) 0.0207(4) Uani 1 1 d . . . H35 H 0.5463 0.0912 0.1073 0.025 Uiso 1 1 calc R . . N36 N 0.55357(10) 0.2895(3) 0.04742(7) 0.0197(4) Uani 1 1 d . . . H36A H 0.5758 0.4207 0.0440 0.030 Uiso 1 1 calc R . . H36B H 0.4990 0.2869 0.0293 0.030 Uiso 1 1 calc R . . H36C H 0.5825 0.1872 0.0346 0.030 Uiso 1 1 calc R . . O41 O 0.35761(10) 0.8207(3) 0.08931(6) 0.0301(4) Uani 1 1 d . . . H41 H 0.3541 0.8710 0.0593 0.045 Uiso 1 1 calc R . . C41 C 0.29015(14) 0.8998(4) 0.10891(9) 0.0283(5) Uani 1 1 d . . . H41A H 0.2366 0.8752 0.0828 0.034 Uiso 1 1 calc R . . H41B H 0.2968 1.0561 0.1150 0.034 Uiso 1 1 calc R . . C42 C 0.28817(16) 0.7884(4) 0.15928(10) 0.0338(6) Uani 1 1 d . . . H42A H 0.3429 0.8094 0.1845 0.041 Uiso 1 1 calc R . . H42B H 0.2450 0.8575 0.1740 0.041 Uiso 1 1 calc R . . C43 C 0.27018(17) 0.5521(4) 0.15388(11) 0.0385(6) Uani 1 1 d . . . H43A H 0.3134 0.4815 0.1395 0.046 Uiso 1 1 calc R . . H43B H 0.2154 0.5297 0.1288 0.046 Uiso 1 1 calc R . . C44 C 0.26874(19) 0.4484(5) 0.20599(12) 0.0462(7) Uani 1 1 d . . . H44A H 0.3234 0.4666 0.2306 0.069 Uiso 1 1 calc R . . H44B H 0.2564 0.2952 0.2007 0.069 Uiso 1 1 calc R . . H44C H 0.2255 0.5167 0.2202 0.069 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 C1 0.0192(14) 0.086(3) 0.203(5) -0.101(3) 0.018(2) -0.0025(16) C2 0.0293(16) 0.080(3) 0.181(5) -0.098(3) 0.020(2) -0.0037(17) C3 0.0259(13) 0.0374(15) 0.0630(19) -0.0246(14) 0.0047(12) -0.0030(11) C4 0.0230(10) 0.0196(11) 0.0184(10) 0.0016(8) 0.0039(8) 0.0003(8) C5 0.0219(10) 0.0207(11) 0.0183(10) 0.0027(8) 0.0060(8) 0.0004(8) C6 0.0200(11) 0.0309(14) 0.0562(17) -0.0140(12) 0.0031(11) 0.0009(10) C7 0.0210(13) 0.049(2) 0.139(4) -0.047(2) 0.0027(17) 0.0014(13) C8 0.0185(12) 0.0454(17) 0.077(2) -0.0117(16) -0.0036(13) -0.0032(12) C9 0.0314(13) 0.0442(16) 0.0276(12) -0.0085(11) 0.0092(10) -0.0163(11) C10 0.0359(15) 0.0534(19) 0.065(2) -0.0359(16) 0.0282(14) -0.0175(13) C11 0.0243(11) 0.0336(13) 0.0308(12) -0.0087(10) 0.0126(9) -0.0084(10) C12 0.0229(11) 0.0268(13) 0.0388(13) -0.0048(10) 0.0020(10) -0.0002(10) C13 0.0250(12) 0.0395(15) 0.0608(18) -0.0273(13) 0.0180(12) -0.0109(11) C14 0.0212(10) 0.0245(11) 0.0152(10) 0.0012(8) 0.0032(8) 0.0001(9) O15 0.0237(8) 0.0253(9) 0.0358(9) 0.0012(7) 0.0090(7) 0.0039(7) O16 0.0203(8) 0.0298(9) 0.0282(8) 0.0056(7) 0.0007(6) -0.0060(7) C21 0.0129(9) 0.0238(11) 0.0231(11) 0.0006(8) 0.0022(8) 0.0022(8) C22 0.0223(11) 0.0229(11) 0.0242(11) -0.0038(9) 0.0052(8) -0.0020(9) C23 0.0264(11) 0.0264(12) 0.0274(12) 0.0030(9) 0.0069(9) -0.0017(9) C24 0.0266(12) 0.0386(14) 0.0204(11) -0.0004(10) 0.0028(9) 0.0024(10) C25 0.0333(13) 0.0310(13) 0.0277(12) -0.0095(10) 0.0013(10) -0.0028(10) C26 0.0266(12) 0.0226(12) 0.0319(12) -0.0012(9) 0.0048(9) -0.0032(9) C27 0.0152(10) 0.0229(11) 0.0245(11) 0.0024(9) 0.0036(8) 0.0014(8) O28 0.0240(8) 0.0239(8) 0.0349(9) 0.0077(7) 0.0102(7) 0.0066(7) C29 0.0174(10) 0.0261(12) 0.0196(10) -0.0003(8) 0.0045(8) 0.0038(8) C30 0.0219(11) 0.0331(13) 0.0299(12) 0.0090(10) 0.0065(9) 0.0031(10) C31 0.0227(11) 0.0482(16) 0.0288(12) 0.0141(11) 0.0019(9) 0.0066(11) C32 0.0171(10) 0.0482(16) 0.0248(12) -0.0013(11) 0.0010(9) 0.0017(10) C33 0.0224(11) 0.0328(13) 0.0289(12) -0.0042(10) 0.0044(9) -0.0022(10) C34 0.0223(11) 0.0246(12) 0.0238(11) 0.0010(9) 0.0035(8) 0.0028(9) C35 0.0190(10) 0.0205(11) 0.0216(10) 0.0035(8) 0.0031(8) 0.0018(8) N36 0.0164(8) 0.0203(9) 0.0214(9) 0.0013(7) 0.0027(7) 0.0010(7) O41 0.0291(9) 0.0305(9) 0.0308(9) 0.0036(7) 0.0079(7) 0.0096(7) C41 0.0251(11) 0.0272(12) 0.0324(12) -0.0023(10) 0.0066(9) 0.0011(10) C42 0.0326(13) 0.0343(14) 0.0344(13) -0.0035(11) 0.0078(10) -0.0047(11) C43 0.0379(14) 0.0350(15) 0.0452(16) -0.0031(12) 0.0153(12) -0.0053(12) C44 0.0447(16) 0.0417(17) 0.0519(18) 0.0097(14) 0.0115(13) -0.0092(13) _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 C6 1.362(4) . ? C1 C2 1.378(4) . ? C2 C3 1.375(4) . ? C3 C4 1.383(3) . ? C4 C5 1.399(3) . ? C4 C14 1.499(3) . ? C5 C6 1.388(3) . ? C5 C13 1.497(3) . ? C6 C12 1.463(3) . ? C7 C12 1.378(4) . ? C7 C8 1.380(4) . ? C8 C9 1.354(4) . ? C9 C10 1.379(4) . ? C10 C11 1.379(3) . ? C11 C12 1.374(3) . ? C11 C13 1.511(3) . ? C14 O16 1.250(3) . ? C14 O15 1.261(3) . ? C21 C22 1.382(3) . ? C21 C26 1.385(3) . ? C21 C27 1.514(3) . ? C22 C23 1.386(3) . ? C23 C24 1.380(3) . ? C24 C25 1.378(4) . ? C25 C26 1.385(3) . ? C27 O28 1.412(3) . ? C27 C35 1.542(3) . ? C29 C30 1.388(3) . ? C29 C34 1.389(3) . ? C29 C35 1.513(3) . ? C30 C31 1.389(3) . ? C31 C32 1.375(4) . ? C32 C33 1.380(3) . ? C33 C34 1.388(3) . ? C35 N36 1.491(3) . ? O41 C41 1.425(3) . ? C41 C42 1.508(3) . ? C42 C43 1.504(4) . ? C43 C44 1.526(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 119.4(3) . . ? C3 C2 C1 120.8(3) . . ? C2 C3 C4 120.5(2) . . ? C3 C4 C5 118.6(2) . . ? C3 C4 C14 118.8(2) . . ? C5 C4 C14 122.55(19) . . ? C6 C5 C4 119.8(2) . . ? C6 C5 C13 109.5(2) . . ? C4 C5 C13 130.7(2) . . ? C1 C6 C5 120.9(2) . . ? C1 C6 C12 130.0(2) . . ? C5 C6 C12 109.1(2) . . ? C12 C7 C8 119.3(3) . . ? C9 C8 C7 120.6(2) . . ? C8 C9 C10 120.3(2) . . ? C11 C10 C9 119.9(3) . . ? C12 C11 C10 119.6(2) . . ? C12 C11 C13 110.1(2) . . ? C10 C11 C13 130.3(2) . . ? C11 C12 C7 120.4(2) . . ? C11 C12 C6 108.5(2) . . ? C7 C12 C6 131.2(2) . . ? C5 C13 C11 102.90(19) . . ? O16 C14 O15 124.5(2) . . ? O16 C14 C4 118.71(19) . . ? O15 C14 C4 116.68(19) . . ? C22 C21 C26 119.1(2) . . ? C22 C21 C27 119.74(19) . . ? C26 C21 C27 121.1(2) . . ? C21 C22 C23 120.7(2) . . ? C24 C23 C22 119.8(2) . . ? C25 C24 C23 119.8(2) . . ? C24 C25 C26 120.3(2) . . ? C25 C26 C21 120.2(2) . . ? O28 C27 C21 113.54(18) . . ? O28 C27 C35 107.30(17) . . ? C21 C27 C35 110.48(17) . . ? C30 C29 C34 119.0(2) . . ? C30 C29 C35 119.0(2) . . ? C34 C29 C35 121.96(19) . . ? C29 C30 C31 120.4(2) . . ? C32 C31 C30 120.0(2) . . ? C31 C32 C33 120.2(2) . . ? C32 C33 C34 120.0(2) . . ? C33 C34 C29 120.3(2) . . ? N36 C35 C29 110.98(17) . . ? N36 C35 C27 108.47(16) . . ? C29 C35 C27 113.65(18) . . ? O41 C41 C42 110.4(2) . . ? C43 C42 C41 114.5(2) . . ? C42 C43 C44 112.1(2) . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 27.93 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.694 _refine_diff_density_min -0.560 _refine_diff_density_rms 0.058 #==END