Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 # TITLE OF THE PAPER _publ_contact_author ; J. Sivaguru Dunbar Hall Department of Chemistry North Dakota State University Fargo, ND 58105 USA ; _publ_contact_author_phone 'Intl. Code + (701)231-8923' _publ_contact_author_fax 'Intl. Code + (701)231-8831' _publ_contact_author_email sivaguru.jayaraman@ndsu.edu _publ_requested_coeditor_name ? #=================================================================== # Title and Author List _publ_section_title ; TITLE OF THE PAPER ; _publ_section_abstract ; ABSTRACT ; loop_ _publ_author_name _publ_author_address 'Josepha L. Jesuraj' ; Dunbar Hall Department of Chemistry North Dakota State University Fargo, ND 58105 USA ; 'J. Sivaguru' ; Dunbar Hall Department of Chemistry North Dakota State University Fargo, ND 58105 USA ; _publ_requested_category FO _publ_contact_author_name 'J. Sivaguru' #======================================================================= data_benzoylformamide-1a _database_code_depnum_ccdc_archive 'CCDC 759989' #TrackingRef 'X-ray-revised.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H25 N O2' _chemical_formula_weight 323.42 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 8.698(4) _cell_length_b 16.685(8) _cell_length_c 13.029(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.478(9) _cell_angle_gamma 90.00 _cell_volume 1864.9(15) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 863 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 23.27 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.78 _exptl_crystal_size_mid 0.72 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.152 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9370 _exptl_absorpt_correction_T_max 0.9927 _exptl_absorpt_process_details 'SADABS (SAINT 6.45A)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13735 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 24.96 _reflns_number_total 3261 _reflns_number_gt 2131 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1000P)^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 3261 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1568 _refine_ls_wR_factor_gt 0.1377 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.030 _refine_ls_shift/su_mean 0.004 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 -0.3924(3) 0.4728(2) 0.6443(2) 0.1022(8) Uani 1 1 d . . . H1 H -0.4523 0.5125 0.6069 0.123 Uiso 1 1 calc R . . C2 C -0.4118(3) 0.3947(2) 0.61323(19) 0.0977(8) Uani 1 1 d . . . H2 H -0.4848 0.3818 0.5550 0.117 Uiso 1 1 calc R . . C3 C -0.2854(3) 0.49335(15) 0.73018(19) 0.0892(7) Uani 1 1 d . . . H3 H -0.2733 0.5465 0.7513 0.107 Uiso 1 1 calc R . . C4 C -0.3243(2) 0.33487(16) 0.66728(17) 0.0799(6) Uani 1 1 d . . . H4 H -0.3384 0.2818 0.6460 0.096 Uiso 1 1 calc R . . C5 C -0.1959(2) 0.43367(13) 0.78475(16) 0.0714(6) Uani 1 1 d . . . H5 H -0.1226 0.4471 0.8425 0.086 Uiso 1 1 calc R . . C6 C 0.1903(2) 0.32936(13) 0.54416(13) 0.0661(5) Uani 1 1 d . . . H6 H 0.1964 0.3291 0.4736 0.079 Uiso 1 1 calc R . . C7 C 0.1402(2) 0.39638(10) 0.69447(12) 0.0532(5) Uani 1 1 d . . . H7 H 0.1135 0.4429 0.7266 0.064 Uiso 1 1 calc R . . C8 C 0.2224(2) 0.26107(11) 0.60150(13) 0.0603(5) Uani 1 1 d . . . H8 H 0.2513 0.2155 0.5681 0.072 Uiso 1 1 calc R . . C9 C 0.1491(2) 0.39821(12) 0.59012(13) 0.0639(5) Uani 1 1 d . . . H9 H 0.1276 0.4450 0.5517 0.077 Uiso 1 1 calc R . . C10 C -0.2144(2) 0.35434(12) 0.75421(14) 0.0623(5) Uani 1 1 d . . . C11 C -0.1176(2) 0.29038(13) 0.81092(15) 0.0639(5) Uani 1 1 d . . . C12 C 0.2866(2) 0.36525(11) 0.94026(13) 0.0591(5) Uani 1 1 d . . . C13 C 0.0201(2) 0.31572(11) 0.89314(13) 0.0584(5) Uani 1 1 d . . . C14 C 0.2549(2) 0.17382(10) 0.76031(13) 0.0564(5) Uani 1 1 d . . . C15 C 0.21433(19) 0.25577(9) 0.70863(12) 0.0467(4) Uani 1 1 d . . . C16 C 0.17009(17) 0.32697(9) 0.75317(11) 0.0429(4) Uani 1 1 d . . . C17 C 0.1373(3) 0.11187(12) 0.70542(18) 0.0815(6) Uani 1 1 d . . . H17A H 0.1370 0.1137 0.6317 0.122 Uiso 1 1 calc R . . H17B H 0.0349 0.1242 0.7194 0.122 Uiso 1 1 calc R . . H17C H 0.1668 0.0592 0.7310 0.122 Uiso 1 1 calc R . . C18 C 0.4213(2) 0.14992(13) 0.74551(17) 0.0772(6) Uani 1 1 d . . . H18A H 0.4300 0.1535 0.6731 0.116 Uiso 1 1 calc R . . H18B H 0.4422 0.0959 0.7693 0.116 Uiso 1 1 calc R . . H18C H 0.4953 0.1855 0.7849 0.116 Uiso 1 1 calc R . . C19 C 0.2489(3) 0.16662(12) 0.87677(15) 0.0732(6) Uani 1 1 d . . . H19A H 0.2769 0.1131 0.8997 0.110 Uiso 1 1 calc R . . H19B H 0.1453 0.1783 0.8889 0.110 Uiso 1 1 calc R . . H19C H 0.3208 0.2040 0.9147 0.110 Uiso 1 1 calc R . . C20 C 0.2454(3) 0.44689(13) 0.97862(16) 0.0884(7) Uani 1 1 d . . . H20A H 0.1500 0.4433 1.0063 0.133 Uiso 1 1 calc R . . H20B H 0.2326 0.4843 0.9218 0.133 Uiso 1 1 calc R . . H20C H 0.3275 0.4649 1.0320 0.133 Uiso 1 1 calc R . . C21 C 0.4381(2) 0.36747(13) 0.89719(15) 0.0756(6) Uani 1 1 d . . . H21A H 0.4611 0.3149 0.8740 0.113 Uiso 1 1 calc R . . H21B H 0.5209 0.3848 0.9506 0.113 Uiso 1 1 calc R . . H21C H 0.4282 0.4041 0.8397 0.113 Uiso 1 1 calc R . . N1 N 0.15599(15) 0.33341(8) 0.86194(9) 0.0476(4) Uani 1 1 d . . . O1 O -0.14767(18) 0.21952(10) 0.79935(13) 0.0950(5) Uani 1 1 d . . . O2 O -0.00084(17) 0.31861(9) 0.98418(10) 0.0845(5) Uani 1 1 d . . . H12 H 0.2939(19) 0.3260(10) 0.9954(13) 0.060(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0832(18) 0.142(3) 0.0832(17) 0.0099(17) 0.0191(14) 0.0334(17) C2 0.0712(16) 0.151(3) 0.0705(14) -0.0081(16) 0.0120(12) 0.0018(17) C3 0.0822(16) 0.0940(18) 0.0955(17) -0.0071(14) 0.0275(13) 0.0216(13) C4 0.0637(14) 0.1067(18) 0.0735(13) -0.0184(13) 0.0241(11) -0.0142(12) C5 0.0608(12) 0.0835(15) 0.0728(12) -0.0139(11) 0.0192(10) 0.0089(11) C6 0.0734(13) 0.0852(15) 0.0408(9) 0.0022(9) 0.0126(9) -0.0022(10) C7 0.0561(11) 0.0501(11) 0.0548(10) 0.0011(8) 0.0131(8) 0.0003(8) C8 0.0660(12) 0.0677(13) 0.0492(10) -0.0119(9) 0.0153(8) -0.0015(9) C9 0.0649(12) 0.0715(14) 0.0545(11) 0.0159(9) 0.0079(9) 0.0032(9) C10 0.0491(11) 0.0801(15) 0.0632(11) -0.0127(10) 0.0260(9) -0.0064(10) C11 0.0561(12) 0.0671(14) 0.0761(12) -0.0121(10) 0.0327(10) -0.0110(10) C12 0.0749(13) 0.0585(12) 0.0432(10) -0.0035(8) 0.0079(9) -0.0123(9) C13 0.0648(12) 0.0571(12) 0.0584(11) -0.0015(8) 0.0247(9) -0.0020(9) C14 0.0630(12) 0.0487(11) 0.0596(10) -0.0059(8) 0.0163(8) -0.0003(8) C15 0.0444(9) 0.0507(10) 0.0461(9) -0.0045(7) 0.0111(7) -0.0057(7) C16 0.0413(9) 0.0476(10) 0.0409(8) -0.0019(7) 0.0096(6) -0.0051(7) C17 0.0940(16) 0.0499(12) 0.1006(16) -0.0115(11) 0.0158(13) -0.0082(10) C18 0.0746(14) 0.0693(14) 0.0903(15) 0.0035(11) 0.0212(11) 0.0160(11) C19 0.0940(15) 0.0536(12) 0.0745(13) 0.0141(9) 0.0216(11) 0.0074(10) C20 0.1163(19) 0.0739(15) 0.0756(13) -0.0262(11) 0.0172(13) -0.0173(13) C21 0.0670(13) 0.0919(16) 0.0642(12) -0.0085(10) -0.0004(10) -0.0210(11) N1 0.0544(8) 0.0493(8) 0.0419(7) -0.0041(6) 0.0163(6) -0.0054(6) O1 0.0767(11) 0.0711(11) 0.1402(14) -0.0132(9) 0.0266(10) -0.0200(8) O2 0.0932(11) 0.1081(12) 0.0623(8) 0.0003(7) 0.0421(8) -0.0077(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 C1 C2 1.367(4) . ? C1 C3 1.376(3) . ? C1 H1 0.9300 . ? C2 C4 1.376(4) . ? C2 H2 0.9300 . ? C3 C5 1.386(3) . ? C3 H3 0.9300 . ? C4 C10 1.395(3) . ? C4 H4 0.9300 . ? C5 C10 1.384(3) . ? C5 H5 0.9300 . ? C6 C8 1.366(3) . ? C6 C9 1.370(3) . ? C6 H6 0.9300 . ? C7 C9 1.375(2) . ? C7 C16 1.388(2) . ? C7 H7 0.9300 . ? C8 C15 1.412(2) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.480(3) . ? C11 O1 1.215(2) . ? C11 C13 1.529(3) . ? C12 N1 1.494(2) . ? C12 C20 1.514(3) . ? C12 C21 1.515(3) . ? C12 H12 0.966(17) . ? C13 O2 1.230(2) . ? C13 N1 1.345(2) . ? C14 C19 1.531(2) . ? C14 C15 1.539(2) . ? C14 C18 1.544(3) . ? C14 C17 1.545(3) . ? C15 C16 1.403(2) . ? C16 N1 1.4464(19) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? 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 C3 120.9(2) . . ? C2 C1 H1 119.6 . . ? C3 C1 H1 119.6 . . ? C1 C2 C4 120.6(2) . . ? C1 C2 H2 119.7 . . ? C4 C2 H2 119.7 . . ? C1 C3 C5 119.0(2) . . ? C1 C3 H3 120.5 . . ? C5 C3 H3 120.5 . . ? C2 C4 C10 119.6(2) . . ? C2 C4 H4 120.2 . . ? C10 C4 H4 120.2 . . ? C10 C5 C3 120.7(2) . . ? C10 C5 H5 119.6 . . ? C3 C5 H5 119.6 . . ? C8 C6 C9 120.34(16) . . ? C8 C6 H6 119.8 . . ? C9 C6 H6 119.8 . . ? C9 C7 C16 121.84(16) . . ? C9 C7 H7 119.1 . . ? C16 C7 H7 119.1 . . ? C6 C8 C15 123.64(17) . . ? C6 C8 H8 118.2 . . ? C15 C8 H8 118.2 . . ? C6 C9 C7 118.34(17) . . ? C6 C9 H9 120.8 . . ? C7 C9 H9 120.8 . . ? C5 C10 C4 119.2(2) . . ? C5 C10 C11 121.10(18) . . ? C4 C10 C11 119.7(2) . . ? O1 C11 C10 123.13(19) . . ? O1 C11 C13 118.95(19) . . ? C10 C11 C13 117.79(17) . . ? N1 C12 C20 110.54(16) . . ? N1 C12 C21 111.43(14) . . ? C20 C12 C21 111.57(16) . . ? N1 C12 H12 102.5(10) . . ? C20 C12 H12 110.7(10) . . ? C21 C12 H12 109.7(10) . . ? O2 C13 N1 124.05(17) . . ? O2 C13 C11 117.60(16) . . ? N1 C13 C11 118.35(14) . . ? C19 C14 C15 117.41(14) . . ? C19 C14 C18 106.80(16) . . ? C15 C14 C18 109.09(14) . . ? C19 C14 C17 106.16(16) . . ? C15 C14 C17 107.77(15) . . ? C18 C14 C17 109.42(16) . . ? C16 C15 C8 114.67(15) . . ? C16 C15 C14 129.04(14) . . ? C8 C15 C14 116.29(14) . . ? C7 C16 C15 121.16(14) . . ? C7 C16 N1 116.07(14) . . ? C15 C16 N1 122.76(14) . . ? 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 . . ? C14 C19 H19A 109.5 . . ? C14 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C14 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C12 C20 H20A 109.5 . . ? C12 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C12 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C12 C21 H21A 109.5 . . ? C12 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C12 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C13 N1 C16 120.04(13) . . ? C13 N1 C12 118.61(14) . . ? C16 N1 C12 121.20(13) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.150 _refine_diff_density_min -0.138 _refine_diff_density_rms 0.032 #===END data_benzoylformamide-1d _database_code_depnum_ccdc_archive 'CCDC 759990' #TrackingRef 'X-ray-revised.cif.txt' _audit_creation_date 2009-11-14T11:39:20-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C24 H29 N O2' _chemical_formula_weight 363.48 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.312(3) _cell_length_b 8.543(2) _cell_length_c 19.637(5) _cell_angle_alpha 90 _cell_angle_beta 94.405(4) _cell_angle_gamma 90 _cell_volume 2059.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5380 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 25.48 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.172 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.788775 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (SAINT 6.45A)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.061 _diffrn_reflns_av_unetI/netI 0.0512 _diffrn_reflns_number 16527 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 26.05 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 4062 _reflns_number_gt 2861 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0746P)^2^+0.2163P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.036(3) _refine_ls_number_reflns 4062 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1429 _refine_ls_wR_factor_gt 0.1251 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.218 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.051 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N001 N 0.79374(9) 0.12195(13) 0.77175(6) 0.0394(3) Uani 1 1 d . . . O002 O 0.89464(10) 0.34540(13) 0.77450(6) 0.0610(3) Uani 1 1 d . . . O003 O 0.83573(10) 0.2480(2) 0.92116(7) 0.0806(5) Uani 1 1 d . . . C004 C 0.77074(12) 0.13479(17) 0.69618(7) 0.0438(4) Uani 1 1 d . . . H004 H 0.7599 0.246 0.6855 0.053 Uiso 1 1 calc R . . C005 C 0.75833(12) -0.01444(16) 0.80746(7) 0.0395(3) Uani 1 1 d . . . C006 C 0.57970(12) 0.11570(19) 0.85122(8) 0.0481(4) Uani 1 1 d . . . C007 C 0.66108(12) -0.01881(17) 0.84027(7) 0.0422(4) Uani 1 1 d . . . C008 C 1.01004(12) 0.15852(17) 0.89580(8) 0.0444(4) Uani 1 1 d . . . C009 C 0.89666(13) 0.20963(19) 0.87833(8) 0.0491(4) Uani 1 1 d . . . C010 C 1.07554(13) 0.10923(18) 0.84588(8) 0.0489(4) Uani 1 1 d . . . H010 H 1.0481 0.1071 0.8004 0.059 Uiso 1 1 calc R . . C011 C 0.86046(12) 0.22880(18) 0.80278(8) 0.0437(4) Uani 1 1 d . . . C012 C 0.82478(14) -0.14596(18) 0.80494(8) 0.0510(4) Uani 1 1 d . . . H012 H 0.8898 -0.1385 0.7839 0.061 Uiso 1 1 calc R . . C013 C 1.05107(14) 0.1583(2) 0.96382(9) 0.0575(5) Uani 1 1 d . . . H013 H 1.0075 0.1907 0.9978 0.069 Uiso 1 1 calc R . . C014 C 0.63591(15) -0.1654(2) 0.86763(9) 0.0565(4) Uani 1 1 d . . . H014 H 0.572 -0.1746 0.8896 0.068 Uiso 1 1 calc R . . C015 C 0.60724(14) 0.2761(2) 0.82290(10) 0.0574(4) Uani 1 1 d . . . H01A H 0.6133 0.2683 0.7746 0.086 Uiso 1 1 calc R . . H01B H 0.6751 0.312 0.8448 0.086 Uiso 1 1 calc R . . H01C H 0.5506 0.349 0.8315 0.086 Uiso 1 1 calc R . . C016 C 0.57244(17) 0.1366(2) 0.92856(9) 0.0694(5) Uani 1 1 d . . . H01D H 0.555 0.0381 0.9485 0.104 Uiso 1 1 calc R . . H01E H 0.5167 0.2115 0.9365 0.104 Uiso 1 1 calc R . . H01F H 0.6411 0.1732 0.9489 0.104 Uiso 1 1 calc R . . C017 C 0.70055(18) -0.2955(2) 0.86364(10) 0.0647(5) Uani 1 1 d . . . H017 H 0.6791 -0.39 0.8819 0.078 Uiso 1 1 calc R . . C018 C 0.66779(16) 0.0495(2) 0.67000(8) 0.0649(5) Uani 1 1 d . . . H01G H 0.6067 0.0867 0.6938 0.078 Uiso 1 1 calc R . . H01H H 0.6761 -0.0618 0.6786 0.078 Uiso 1 1 calc R . . C019 C 0.79649(17) -0.2867(2) 0.83280(9) 0.0624(5) Uani 1 1 d . . . H019 H 0.8414 -0.3738 0.8307 0.075 Uiso 1 1 calc R . . C020 C 1.18148(14) 0.0632(2) 0.86325(10) 0.0596(5) Uani 1 1 d . . . H020 H 1.2259 0.032 0.8295 0.071 Uiso 1 1 calc R . . C021 C 1.22099(16) 0.0637(2) 0.93042(10) 0.0656(5) Uani 1 1 d . . . H021 H 1.2923 0.0324 0.9421 0.079 Uiso 1 1 calc R . . C022 C 0.46649(14) 0.0693(3) 0.81817(11) 0.0697(5) Uani 1 1 d . . . H02A H 0.4463 -0.0312 0.8351 0.105 Uiso 1 1 calc R . . H02B H 0.469 0.0643 0.7695 0.105 Uiso 1 1 calc R . . H02C H 0.4137 0.146 0.8294 0.105 Uiso 1 1 calc R . . C023 C 0.84554(19) 0.1029(3) 0.58180(9) 0.0765(6) Uani 1 1 d . . . H02D H 0.8415 0.214 0.5718 0.092 Uiso 1 1 calc R . . H02E H 0.9057 0.0595 0.5588 0.092 Uiso 1 1 calc R . . C024 C 1.15632(16) 0.1099(2) 0.98056(10) 0.0674(5) Uani 1 1 d . . . H024 H 1.1837 0.1085 1.026 0.081 Uiso 1 1 calc R . . C025 C 0.86675(16) 0.0795(2) 0.65862(9) 0.0651(5) Uani 1 1 d . . . H02F H 0.8799 -0.0305 0.6682 0.078 Uiso 1 1 calc R . . H02G H 0.9314 0.1374 0.6749 0.078 Uiso 1 1 calc R . . C026 C 0.64594(19) 0.0783(3) 0.59334(9) 0.0778(6) Uani 1 1 d . . . H02H H 0.5808 0.0221 0.5766 0.093 Uiso 1 1 calc R . . H02I H 0.6333 0.1891 0.5852 0.093 Uiso 1 1 calc R . . C027 C 0.7409(2) 0.0251(3) 0.55490(10) 0.0853(7) Uani 1 1 d . . . H02J H 0.7486 -0.0876 0.5591 0.102 Uiso 1 1 calc R . . H02K H 0.7266 0.0498 0.5068 0.102 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 N001 0.0417(6) 0.0376(7) 0.0396(7) 0.0021(5) 0.0070(5) 0.0001(5) O002 0.0650(7) 0.0484(7) 0.0689(8) 0.0087(6) -0.0002(6) -0.0151(6) O003 0.0541(7) 0.1308(13) 0.0576(8) -0.0269(8) 0.0075(6) 0.0102(8) C004 0.0524(9) 0.0403(8) 0.0392(8) 0.0044(6) 0.0075(6) 0.0007(7) C005 0.0461(8) 0.0370(8) 0.0358(7) 0.0014(6) 0.0045(6) -0.0009(6) C006 0.0413(8) 0.0543(10) 0.0495(9) -0.0023(7) 0.0082(7) 0.0001(7) C007 0.0462(8) 0.0430(8) 0.0373(7) 0.0007(6) 0.0025(6) -0.0049(6) C008 0.0453(8) 0.0415(8) 0.0465(8) -0.0012(6) 0.0037(7) -0.0054(6) C009 0.0468(9) 0.0522(9) 0.0490(9) -0.0075(7) 0.0082(7) -0.0040(7) C010 0.0494(9) 0.0487(9) 0.0486(9) -0.0039(7) 0.0037(7) -0.0025(7) C011 0.0397(8) 0.0404(8) 0.0515(9) -0.0006(7) 0.0066(6) 0.0012(6) C012 0.0607(10) 0.0438(9) 0.0490(9) 0.0011(7) 0.0086(7) 0.0088(7) C013 0.0580(10) 0.0673(11) 0.0473(9) -0.0027(8) 0.0036(8) -0.0084(8) C014 0.0615(10) 0.0541(10) 0.0548(10) 0.0068(8) 0.0103(8) -0.0131(8) C015 0.0506(9) 0.0507(10) 0.0718(11) 0.0006(8) 0.0105(8) 0.0131(8) C016 0.0727(12) 0.0802(14) 0.0575(11) -0.0062(9) 0.0204(9) 0.0068(10) C017 0.0920(14) 0.0389(9) 0.0631(11) 0.0104(8) 0.0046(10) -0.0096(9) C018 0.0732(12) 0.0750(12) 0.0458(10) 0.0001(8) 0.0011(8) -0.0187(10) C019 0.0863(13) 0.0407(9) 0.0604(11) 0.0017(8) 0.0059(10) 0.0119(9) C020 0.0515(10) 0.0556(10) 0.0719(12) -0.0077(8) 0.0065(8) 0.0033(8) C021 0.0526(10) 0.0607(11) 0.0816(13) 0.0024(10) -0.0078(9) 0.0030(9) C022 0.0462(10) 0.0849(14) 0.0779(13) -0.0039(10) 0.0049(9) -0.0040(9) C023 0.1008(16) 0.0795(14) 0.0531(11) 0.0053(10) 0.0313(11) 0.0164(12) C024 0.0666(12) 0.0760(13) 0.0570(11) 0.0070(9) -0.0126(9) -0.0094(10) C025 0.0719(12) 0.0739(13) 0.0519(10) 0.0053(9) 0.0196(9) 0.0144(10) C026 0.0938(15) 0.0895(15) 0.0484(10) -0.0013(10) -0.0059(10) -0.0166(12) C027 0.148(2) 0.0653(13) 0.0431(10) -0.0038(9) 0.0093(12) 0.0009(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N001 C011 1.3426(19) . ? N001 C005 1.4445(18) . ? N001 C004 1.4933(18) . ? O002 C011 1.2303(18) . ? O003 C009 1.214(2) . ? C004 C025 1.516(2) . ? C004 C018 1.517(2) . ? C004 H004 0.98 . ? C005 C012 1.393(2) . ? C005 C007 1.403(2) . ? C006 C015 1.527(2) . ? C006 C016 1.539(2) . ? C006 C022 1.543(2) . ? C006 C007 1.550(2) . ? C007 C014 1.406(2) . ? C008 C010 1.382(2) . ? C008 C013 1.391(2) . ? C008 C009 1.478(2) . ? C009 C011 1.525(2) . ? C010 C020 1.380(2) . ? C010 H010 0.93 . ? C012 C019 1.377(2) . ? C012 H012 0.93 . ? C013 C024 1.376(3) . ? C013 H013 0.93 . ? C014 C017 1.373(3) . ? C014 H014 0.93 . ? C015 H01A 0.96 . ? C015 H01B 0.96 . ? C015 H01C 0.96 . ? C016 H01D 0.96 . ? C016 H01E 0.96 . ? C016 H01F 0.96 . ? C017 C019 1.370(3) . ? C017 H017 0.93 . ? C018 C026 1.529(2) . ? C018 H01G 0.97 . ? C018 H01H 0.97 . ? C019 H019 0.93 . ? C020 C021 1.371(3) . ? C020 H020 0.93 . ? C021 C024 1.371(3) . ? C021 H021 0.93 . ? C022 H02A 0.96 . ? C022 H02B 0.96 . ? C022 H02C 0.96 . ? C023 C027 1.509(3) . ? C023 C025 1.524(3) . ? C023 H02D 0.97 . ? C023 H02E 0.97 . ? C024 H024 0.93 . ? C025 H02F 0.97 . ? C025 H02G 0.97 . ? C026 C027 1.509(3) . ? C026 H02H 0.97 . ? C026 H02I 0.97 . ? C027 H02J 0.97 . ? C027 H02K 0.97 . ? 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 C011 N001 C005 121.67(12) . . ? C011 N001 C004 117.63(12) . . ? C005 N001 C004 120.03(11) . . ? N001 C004 C025 111.42(13) . . ? N001 C004 C018 113.02(12) . . ? C025 C004 C018 110.36(14) . . ? N001 C004 H004 107.2 . . ? C025 C004 H004 107.2 . . ? C018 C004 H004 107.2 . . ? C012 C005 C007 121.27(14) . . ? C012 C005 N001 115.69(13) . . ? C007 C005 N001 122.98(12) . . ? C015 C006 C016 106.65(14) . . ? C015 C006 C022 107.21(14) . . ? C016 C006 C022 109.01(15) . . ? C015 C006 C007 116.80(13) . . ? C016 C006 C007 108.07(13) . . ? C022 C006 C007 108.89(14) . . ? C005 C007 C014 114.83(14) . . ? C005 C007 C006 128.85(13) . . ? C014 C007 C006 116.31(14) . . ? C010 C008 C013 119.46(15) . . ? C010 C008 C009 121.18(14) . . ? C013 C008 C009 119.35(15) . . ? O003 C009 C008 122.81(15) . . ? O003 C009 C011 119.67(15) . . ? C008 C009 C011 117.25(13) . . ? C020 C010 C008 120.24(16) . . ? C020 C010 H010 119.9 . . ? C008 C010 H010 119.9 . . ? O002 C011 N001 124.35(14) . . ? O002 C011 C009 116.21(13) . . ? N001 C011 C009 119.44(13) . . ? C019 C012 C005 121.54(16) . . ? C019 C012 H012 119.2 . . ? C005 C012 H012 119.2 . . ? C024 C013 C008 119.72(17) . . ? C024 C013 H013 120.1 . . ? C008 C013 H013 120.1 . . ? C017 C014 C007 123.59(17) . . ? C017 C014 H014 118.2 . . ? C007 C014 H014 118.2 . . ? C006 C015 H01A 109.5 . . ? C006 C015 H01B 109.5 . . ? H01A C015 H01B 109.5 . . ? C006 C015 H01C 109.5 . . ? H01A C015 H01C 109.5 . . ? H01B C015 H01C 109.5 . . ? C006 C016 H01D 109.5 . . ? C006 C016 H01E 109.5 . . ? H01D C016 H01E 109.5 . . ? C006 C016 H01F 109.5 . . ? H01D C016 H01F 109.5 . . ? H01E C016 H01F 109.5 . . ? C019 C017 C014 120.28(16) . . ? C019 C017 H017 119.9 . . ? C014 C017 H017 119.9 . . ? C004 C018 C026 109.60(15) . . ? C004 C018 H01G 109.8 . . ? C026 C018 H01G 109.8 . . ? C004 C018 H01H 109.8 . . ? C026 C018 H01H 109.8 . . ? H01G C018 H01H 108.2 . . ? C017 C019 C012 118.44(16) . . ? C017 C019 H019 120.8 . . ? C012 C019 H019 120.8 . . ? C021 C020 C010 119.74(17) . . ? C021 C020 H020 120.1 . . ? C010 C020 H020 120.1 . . ? C020 C021 C024 120.62(17) . . ? C020 C021 H021 119.7 . . ? C024 C021 H021 119.7 . . ? C006 C022 H02A 109.5 . . ? C006 C022 H02B 109.5 . . ? H02A C022 H02B 109.5 . . ? C006 C022 H02C 109.5 . . ? H02A C022 H02C 109.5 . . ? H02B C022 H02C 109.5 . . ? C027 C023 C025 111.44(17) . . ? C027 C023 H02D 109.3 . . ? C025 C023 H02D 109.3 . . ? C027 C023 H02E 109.3 . . ? C025 C023 H02E 109.3 . . ? H02D C023 H02E 108 . . ? C021 C024 C013 120.21(17) . . ? C021 C024 H024 119.9 . . ? C013 C024 H024 119.9 . . ? C004 C025 C023 111.10(16) . . ? C004 C025 H02F 109.4 . . ? C023 C025 H02F 109.4 . . ? C004 C025 H02G 109.4 . . ? C023 C025 H02G 109.4 . . ? H02F C025 H02G 108 . . ? C027 C026 C018 111.07(19) . . ? C027 C026 H02H 109.4 . . ? C018 C026 H02H 109.4 . . ? C027 C026 H02I 109.4 . . ? C018 C026 H02I 109.4 . . ? H02H C026 H02I 108 . . ? C023 C027 C026 111.44(16) . . ? C023 C027 H02J 109.3 . . ? C026 C027 H02J 109.3 . . ? C023 C027 H02K 109.3 . . ? C026 C027 H02K 109.3 . . ? H02J C027 H02K 108 . . ? #===END data_cis2a _database_code_depnum_ccdc_archive 'CCDC 759991' #TrackingRef 'X-ray-revised.cif.txt' _audit_creation_date 2010-04-13T12:25:23-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C21 H25 N O2' _chemical_formula_weight 323.42 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.354(4) _cell_length_b 9.792(5) _cell_length_c 10.162(5) _cell_angle_alpha 79.581(9) _cell_angle_beta 85.526(10) _cell_angle_gamma 87.199(10) _cell_volume 912.1(8) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 1573 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 21.19 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description chunk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.66 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.6334 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details 'SADABS v. 2007/4 (SAINT 7.34A)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0597 _diffrn_reflns_av_unetI/netI 0.0859 _diffrn_reflns_number 7296 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 25.3 _diffrn_reflns_theta_full 25.3 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _reflns_number_total 3296 _reflns_number_gt 1749 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker CCD' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0959P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.061(8) _refine_ls_number_reflns 3296 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1201 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1763 _refine_ls_wR_factor_gt 0.1401 _refine_ls_goodness_of_fit_ref 0.938 _refine_ls_restrained_S_all 0.938 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.19 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.048 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.1600(2) 0.61560(19) 0.47392(18) 0.0646(6) Uani 1 1 d . . . N1 N 0.0614(2) 0.6956(2) 0.2731(2) 0.0500(6) Uani 1 1 d . . . O1 O 0.0843(2) 0.5032(2) 0.1799(2) 0.0770(7) Uani 1 1 d . . . C21 C 0.2962(3) 0.4178(2) 0.2926(3) 0.0522(7) Uani 1 1 d . . . C20 C 0.1230(3) 0.6000(3) 0.3648(3) 0.0509(7) Uani 1 1 d . . . C19 C 0.1275(3) 0.9409(3) 0.2637(2) 0.0526(7) Uani 1 1 d . . . C18 C 0.0285(3) 0.8364(3) 0.2922(2) 0.0506(7) Uani 1 1 d . . . C17 C -0.1103(3) 0.8644(4) 0.3430(3) 0.0678(8) Uani 1 1 d . . . C16 C 0.2847(3) 0.9331(3) 0.2075(3) 0.0624(8) Uani 1 1 d . . . C15 C -0.0600(4) 1.0983(4) 0.3356(3) 0.0758(9) Uani 1 1 d . . . C14 C 0.0759(3) 1.0719(3) 0.2872(3) 0.0685(8) Uani 1 1 d . . . C13 C 0.1416(3) 0.4680(3) 0.3069(3) 0.0568(7) Uani 1 1 d . . . C12 C 0.0044(3) 0.6325(3) 0.1678(3) 0.0575(7) Uani 1 1 d . . . C11 C 0.3510(4) 0.7899(4) 0.1972(4) 0.0707(9) Uani 1 1 d . . . C10 C -0.1545(4) 0.9947(4) 0.3641(3) 0.0783(10) Uani 1 1 d . . . C9 C 0.3611(4) 0.4042(3) 0.1687(3) 0.0692(9) Uani 1 1 d . . . C8 C 0.3772(4) 0.3858(3) 0.4019(4) 0.0720(9) Uani 1 1 d . . . C7 C 0.0374(4) 0.7133(4) 0.0304(3) 0.0773(10) Uani 1 1 d . . . C6 C -0.1534(4) 0.6037(4) 0.1927(4) 0.0760(9) Uani 1 1 d . . . C5 C 0.3805(4) 0.9935(5) 0.2952(6) 0.0916(12) Uani 1 1 d . . . C4 C 0.5211(4) 0.3430(4) 0.3857(5) 0.0882(12) Uani 1 1 d . . . C3 C 0.5022(4) 0.3596(4) 0.1552(5) 0.0887(11) Uani 1 1 d . . . C2 C 0.5819(4) 0.3298(4) 0.2628(5) 0.0897(11) Uani 1 1 d . . . C1 C 0.2918(6) 1.0219(6) 0.0657(5) 0.1081(16) Uani 1 1 d . . . H1 H 0.080(3) 0.393(3) 0.352(2) 0.051(7) Uiso 1 1 d . . . H2 H 0.358(3) 0.733(3) 0.280(3) 0.062(9) Uiso 1 1 d . . . H3 H 0.143(4) 0.732(3) 0.006(3) 0.096(11) Uiso 1 1 d . . . H4 H -0.212(3) 0.686(3) 0.174(3) 0.071(9) Uiso 1 1 d . . . H5 H 0.457(4) 0.801(3) 0.171(3) 0.086(9) Uiso 1 1 d . . . H6 H 0.149(3) 1.152(3) 0.268(3) 0.072(8) Uiso 1 1 d . . . H7 H 0.370(4) 0.935(4) 0.381(4) 0.099(14) Uiso 1 1 d . . . H8 H -0.014(4) 0.817(4) 0.019(4) 0.116(12) Uiso 1 1 d . . . H9 H -0.245(4) 1.006(3) 0.396(3) 0.093(11) Uiso 1 1 d . . . H10 H -0.007(4) 0.672(4) -0.032(4) 0.100(11) Uiso 1 1 d . . . H11 H 0.306(4) 0.740(4) 0.127(4) 0.136(15) Uiso 1 1 d . . . H12 H -0.172(3) 0.792(3) 0.365(3) 0.066(8) Uiso 1 1 d . . . H13 H 0.304(4) 0.431(3) 0.099(3) 0.090(11) Uiso 1 1 d . . . H14 H 0.564(4) 0.334(4) 0.457(4) 0.101(13) Uiso 1 1 d . . . H15 H -0.179(3) 0.540(3) 0.123(3) 0.100(10) Uiso 1 1 d . . . H16 H 0.545(4) 0.345(3) 0.065(4) 0.100(11) Uiso 1 1 d . . . H17 H -0.181(4) 0.554(4) 0.285(4) 0.110(13) Uiso 1 1 d . . . H18 H 0.222(6) 0.989(5) 0.002(5) 0.16(2) Uiso 1 1 d . . . H19 H 0.480(5) 0.982(4) 0.248(4) 0.136(15) Uiso 1 1 d . . . H20 H -0.085(3) 1.194(4) 0.350(3) 0.099(10) Uiso 1 1 d . . . H21 H 0.386(5) 1.019(4) 0.034(4) 0.123(14) Uiso 1 1 d . . . H22 H 0.333(3) 0.394(3) 0.490(3) 0.076(9) Uiso 1 1 d . . . H23 H 0.355(5) 1.088(6) 0.298(5) 0.160(19) Uiso 1 1 d . . . H24 H 0.693(4) 0.296(4) 0.249(3) 0.109(11) Uiso 1 1 d . . . H25 H 0.264(5) 1.119(6) 0.065(5) 0.17(2) 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 O2 0.0714(13) 0.0731(13) 0.0533(12) -0.0193(9) -0.0111(9) -0.0028(10) N1 0.0492(13) 0.0517(13) 0.0528(13) -0.0175(11) -0.0082(10) -0.0012(10) O1 0.0842(14) 0.0744(14) 0.0873(15) -0.0439(11) -0.0446(11) 0.0215(11) C21 0.0579(17) 0.0416(14) 0.0591(17) -0.0097(12) -0.0113(13) -0.0060(12) C20 0.0454(15) 0.0543(16) 0.0543(17) -0.0113(13) -0.0048(12) -0.0053(12) C19 0.0536(16) 0.0537(16) 0.0510(15) -0.0116(12) -0.0029(12) 0.0017(13) C18 0.0507(16) 0.0571(17) 0.0457(14) -0.0146(12) -0.0030(11) 0.0021(13) C17 0.0556(19) 0.077(2) 0.073(2) -0.0212(17) 0.0058(15) -0.0047(17) C16 0.0545(17) 0.0567(17) 0.0744(19) -0.0093(15) 0.0040(14) -0.0085(13) C15 0.077(2) 0.066(2) 0.091(2) -0.0317(18) -0.0123(18) 0.0139(19) C14 0.064(2) 0.0600(19) 0.083(2) -0.0175(16) -0.0068(16) 0.0052(16) C13 0.0564(17) 0.0556(17) 0.0637(18) -0.0189(14) -0.0142(14) -0.0061(14) C12 0.0606(17) 0.0610(17) 0.0561(17) -0.0189(13) -0.0192(13) 0.0023(14) C11 0.054(2) 0.073(2) 0.083(3) -0.017(2) 0.0108(17) 0.0026(16) C10 0.063(2) 0.094(3) 0.081(2) -0.0342(19) 0.0074(17) 0.019(2) C9 0.076(2) 0.0645(19) 0.066(2) -0.0066(16) -0.0109(17) 0.0037(16) C8 0.080(2) 0.066(2) 0.072(2) -0.0108(17) -0.0196(18) -0.0001(16) C7 0.083(3) 0.095(3) 0.060(2) -0.0223(19) -0.0148(18) -0.009(2) C6 0.059(2) 0.086(3) 0.090(3) -0.025(2) -0.0239(18) -0.0056(18) C5 0.069(2) 0.073(3) 0.138(4) -0.029(3) -0.009(2) -0.0102(19) C4 0.079(3) 0.075(2) 0.114(3) -0.010(2) -0.049(3) 0.0045(18) C3 0.085(3) 0.076(2) 0.099(3) -0.010(2) 0.016(2) 0.0073(19) C2 0.070(3) 0.067(2) 0.130(4) -0.012(2) -0.006(3) -0.0047(18) C1 0.078(3) 0.122(4) 0.099(3) 0.031(3) 0.026(3) 0.005(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O2 C20 1.224(3) . ? N1 C20 1.338(3) . ? N1 C18 1.442(3) . ? N1 C12 1.474(3) . ? O1 C13 1.414(3) . ? O1 C12 1.429(3) . ? C21 C8 1.375(4) . ? C21 C9 1.380(4) . ? C21 C13 1.509(4) . ? C20 C13 1.511(4) . ? C19 C18 1.390(4) . ? C19 C14 1.402(4) . ? C19 C16 1.539(4) . ? C18 C17 1.393(4) . ? C17 C10 1.370(4) . ? C17 H12 0.92(3) . ? C16 C5 1.521(5) . ? C16 C11 1.523(4) . ? C16 C1 1.542(5) . ? C15 C10 1.355(5) . ? C15 C14 1.357(4) . ? C15 H20 0.99(3) . ? C14 H6 1.05(3) . ? C13 H1 0.98(3) . ? C12 C7 1.492(4) . ? C12 C6 1.509(4) . ? C11 H2 0.93(3) . ? C11 H5 1.01(3) . ? C11 H11 1.06(5) . ? C10 H9 0.89(3) . ? C9 C3 1.374(5) . ? C9 H13 0.91(3) . ? C8 C4 1.397(5) . ? C8 H22 0.97(3) . ? C7 H3 1.02(3) . ? C7 H8 1.09(4) . ? C7 H10 0.94(4) . ? C6 H4 0.95(3) . ? C6 H15 1.07(4) . ? C6 H17 1.00(4) . ? C5 H7 0.95(4) . ? C5 H19 1.02(4) . ? C5 H23 0.95(5) . ? C4 C2 1.356(6) . ? C4 H14 0.85(4) . ? C3 C2 1.352(5) . ? C3 H16 1.00(4) . ? C2 H24 1.08(4) . ? C1 H18 1.05(6) . ? C1 H21 0.92(4) . ? C1 H25 0.97(6) . ? 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 C20 N1 C18 122.9(2) . . ? C20 N1 C12 111.7(2) . . ? C18 N1 C12 124.1(2) . . ? C13 O1 C12 111.11(18) . . ? C8 C21 C9 117.9(3) . . ? C8 C21 C13 121.2(3) . . ? C9 C21 C13 120.9(2) . . ? O2 C20 N1 127.2(2) . . ? O2 C20 C13 125.9(2) . . ? N1 C20 C13 106.8(2) . . ? C18 C19 C14 115.4(2) . . ? C18 C19 C16 128.8(2) . . ? C14 C19 C16 115.8(2) . . ? C19 C18 C17 120.2(3) . . ? C19 C18 N1 123.4(2) . . ? C17 C18 N1 116.4(2) . . ? C10 C17 C18 121.7(3) . . ? C10 C17 H12 119.8(17) . . ? C18 C17 H12 118.4(17) . . ? C5 C16 C11 105.3(3) . . ? C5 C16 C19 109.8(3) . . ? C11 C16 C19 117.5(2) . . ? C5 C16 C1 109.5(4) . . ? C11 C16 C1 108.0(3) . . ? C19 C16 C1 106.6(3) . . ? C10 C15 C14 119.9(3) . . ? C10 C15 H20 122.7(19) . . ? C14 C15 H20 117.4(19) . . ? C15 C14 C19 123.9(3) . . ? C15 C14 H6 119.4(14) . . ? C19 C14 H6 116.7(15) . . ? O1 C13 C21 110.7(2) . . ? O1 C13 C20 104.3(2) . . ? C21 C13 C20 113.1(2) . . ? O1 C13 H1 101.7(14) . . ? C21 C13 H1 111.4(13) . . ? C20 C13 H1 114.6(14) . . ? O1 C12 N1 101.64(19) . . ? O1 C12 C7 108.4(3) . . ? N1 C12 C7 112.6(2) . . ? O1 C12 C6 108.9(3) . . ? N1 C12 C6 113.3(2) . . ? C7 C12 C6 111.3(3) . . ? C16 C11 H2 112.8(17) . . ? C16 C11 H5 107.6(17) . . ? H2 C11 H5 98(2) . . ? C16 C11 H11 115(2) . . ? H2 C11 H11 113(3) . . ? H5 C11 H11 109(3) . . ? C15 C10 C17 118.9(3) . . ? C15 C10 H9 124(2) . . ? C17 C10 H9 117(2) . . ? C3 C9 C21 121.1(3) . . ? C3 C9 H13 124(2) . . ? C21 C9 H13 115(2) . . ? C21 C8 C4 120.2(4) . . ? C21 C8 H22 118.9(18) . . ? C4 C8 H22 121.0(18) . . ? C12 C7 H3 115.1(18) . . ? C12 C7 H8 111.3(19) . . ? H3 C7 H8 104(3) . . ? C12 C7 H10 109(2) . . ? H3 C7 H10 114(3) . . ? H8 C7 H10 103(3) . . ? C12 C6 H4 112.0(18) . . ? C12 C6 H15 107.4(17) . . ? H4 C6 H15 106(2) . . ? C12 C6 H17 114(2) . . ? H4 C6 H17 109(3) . . ? H15 C6 H17 108(3) . . ? C16 C5 H7 105(2) . . ? C16 C5 H19 102(2) . . ? H7 C5 H19 113(3) . . ? C16 C5 H23 111(3) . . ? H7 C5 H23 113(4) . . ? H19 C5 H23 112(4) . . ? C2 C4 C8 120.6(4) . . ? C2 C4 H14 126(2) . . ? C8 C4 H14 113(3) . . ? C2 C3 C9 120.8(4) . . ? C2 C3 H16 120(2) . . ? C9 C3 H16 119(2) . . ? C3 C2 C4 119.5(4) . . ? C3 C2 H24 119.3(18) . . ? C4 C2 H24 121.3(18) . . ? C16 C1 H18 113(3) . . ? C16 C1 H21 106(2) . . ? H18 C1 H21 113(4) . . ? C16 C1 H25 113(3) . . ? H18 C1 H25 104(4) . . ? H21 C1 H25 107(4) . . ? #===END data_trans-2d _database_code_depnum_ccdc_archive 'CCDC 759992' #TrackingRef 'X-ray-revised.cif.txt' _audit_creation_date 2009-11-20T15:40:06-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C24 H29 N1 O2' _chemical_formula_sum 'C24 H29 N O2' _chemical_formula_weight 363.48 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 12.223(8) _cell_length_b 10.426(6) _cell_length_c 16.072(10) _cell_angle_alpha 90 _cell_angle_beta 93.259(9) _cell_angle_gamma 90 _cell_volume 2045(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5964 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 25.04 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description chunk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.36 _exptl_crystal_density_diffrn 1.181 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.6358 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details 'SADABS (SAINT 6.45A)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0555 _diffrn_reflns_av_unetI/netI 0.0465 _diffrn_reflns_number 13837 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 25.18 _diffrn_reflns_theta_full 25.18 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 3657 _reflns_number_gt 2776 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0711P)^2^+0.2836P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.026(3) _refine_ls_number_reflns 3657 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1394 _refine_ls_wR_factor_gt 0.1263 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.226 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.05 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O001 O 0.56851(9) 0.15173(11) 0.04785(6) 0.0510(3) Uani 1 1 d . . . O002 O 0.76646(10) -0.05015(11) 0.14759(7) 0.0590(4) Uani 1 1 d . . . N003 N 0.62064(10) 0.07911(11) 0.17797(7) 0.0394(3) Uani 1 1 d . . . C004 C 0.62488(12) 0.05862(14) 0.26687(9) 0.0399(4) Uani 1 1 d . . . C005 C 0.69192(13) 0.02333(14) 0.12742(9) 0.0429(4) Uani 1 1 d . . . C006 C 0.65577(13) 0.06303(14) 0.03883(9) 0.0441(4) Uani 1 1 d . . . H006 H 0.6248 -0.0129 0.0104 0.053 Uiso 1 1 calc R . . C007 C 0.55533(13) 0.18167(14) 0.13461(9) 0.0413(4) Uani 1 1 d . . . C008 C 0.74614(13) 0.11358(15) -0.01289(9) 0.0457(4) Uani 1 1 d . . . C009 C 0.60057(15) 0.31556(15) 0.15395(11) 0.0532(4) Uani 1 1 d . . . H00A H 0.6765 0.3196 0.1395 0.064 Uiso 1 1 calc R . . H00B H 0.5984 0.3319 0.2132 0.064 Uiso 1 1 calc R . . C010 C 0.57185(13) -0.04427(15) 0.30494(10) 0.0460(4) Uani 1 1 d . . . C011 C 0.68637(14) 0.14737(15) 0.31448(10) 0.0498(4) Uani 1 1 d . . . H011 H 0.7228 0.2122 0.2876 0.06 Uiso 1 1 calc R . . C012 C 0.74760(17) 0.23783(17) -0.04139(11) 0.0607(5) Uani 1 1 d . . . H012 H 0.692 0.2939 -0.0282 0.073 Uiso 1 1 calc R . . C013 C 0.43387(14) 0.17460(17) 0.14964(10) 0.0512(4) Uani 1 1 d . . . H01A H 0.4237 0.185 0.2087 0.061 Uiso 1 1 calc R . . H01B H 0.406 0.0908 0.1329 0.061 Uiso 1 1 calc R . . C014 C 0.50255(16) -0.15407(16) 0.26352(11) 0.0572(5) Uani 1 1 d . . . C015 C 0.51451(16) -0.17554(17) 0.17026(11) 0.0604(5) Uani 1 1 d . . . H01C H 0.4684 -0.2454 0.1514 0.091 Uiso 1 1 calc R . . H01D H 0.5894 -0.1955 0.1607 0.091 Uiso 1 1 calc R . . H01E H 0.4933 -0.0991 0.1402 0.091 Uiso 1 1 calc R . . C016 C 0.58220(17) -0.04460(18) 0.39249(11) 0.0621(5) Uani 1 1 d . . . H016 H 0.5473 -0.1094 0.4207 0.075 Uiso 1 1 calc R . . C017 C 0.82976(18) 0.0317(2) -0.03443(13) 0.0750(6) Uani 1 1 d . . . H017 H 0.8293 -0.0535 -0.0172 0.09 Uiso 1 1 calc R . . C018 C 0.36942(16) 0.2780(2) 0.10100(12) 0.0675(5) Uani 1 1 d . . . H01F H 0.3739 0.2627 0.0417 0.081 Uiso 1 1 calc R . . H01G H 0.2929 0.2732 0.1138 0.081 Uiso 1 1 calc R . . C019 C 0.69475(16) 0.14198(18) 0.39997(11) 0.0613(5) Uani 1 1 d . . . H019 H 0.7359 0.2023 0.4308 0.074 Uiso 1 1 calc R . . C020 C 0.64100(17) 0.04545(19) 0.43892(11) 0.0673(5) Uani 1 1 d . . . H020 H 0.6443 0.0409 0.4968 0.081 Uiso 1 1 calc R . . C021 C 0.53439(18) 0.41959(18) 0.10548(14) 0.0705(6) Uani 1 1 d . . . H02A H 0.5621 0.5036 0.1219 0.085 Uiso 1 1 calc R . . H02B H 0.5434 0.4093 0.0463 0.085 Uiso 1 1 calc R . . C022 C 0.8310(2) 0.2809(2) -0.08972(13) 0.0778(6) Uani 1 1 d . . . H022 H 0.8302 0.365 -0.109 0.093 Uiso 1 1 calc R . . C023 C 0.91442(19) 0.2004(3) -0.10916(13) 0.0798(7) Uani 1 1 d . . . H023 H 0.9707 0.2299 -0.1408 0.096 Uiso 1 1 calc R . . C024 C 0.41334(19) 0.4110(2) 0.12225(14) 0.0782(6) Uani 1 1 d . . . H02C H 0.4035 0.4293 0.1805 0.094 Uiso 1 1 calc R . . H02D H 0.3727 0.4744 0.0889 0.094 Uiso 1 1 calc R . . C025 C 0.38030(18) -0.1258(3) 0.27691(15) 0.0890(7) Uani 1 1 d . . . H02E H 0.371 -0.1114 0.3351 0.134 Uiso 1 1 calc R . . H02F H 0.3365 -0.1978 0.2582 0.134 Uiso 1 1 calc R . . H02G H 0.3577 -0.0509 0.2458 0.134 Uiso 1 1 calc R . . C026 C 0.5365(3) -0.2826(2) 0.30629(16) 0.1019(9) Uani 1 1 d . . . H02H H 0.5313 -0.2746 0.3654 0.153 Uiso 1 1 calc R . . H02I H 0.6105 -0.3029 0.2943 0.153 Uiso 1 1 calc R . . H02J H 0.4885 -0.3497 0.2856 0.153 Uiso 1 1 calc R . . C027 C 0.9142(2) 0.0759(3) -0.08159(15) 0.0902(8) Uani 1 1 d . . . H027 H 0.9707 0.0208 -0.0944 0.108 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 O001 0.0506(7) 0.0699(7) 0.0325(6) 0.0015(5) 0.0025(5) 0.0146(5) O002 0.0626(8) 0.0525(7) 0.0625(8) 0.0079(5) 0.0085(6) 0.0174(6) N003 0.0444(7) 0.0401(7) 0.0335(6) 0.0025(5) 0.0012(5) 0.0026(5) C004 0.0418(9) 0.0431(8) 0.0345(8) 0.0032(6) 0.0004(6) 0.0035(6) C005 0.0482(9) 0.0367(7) 0.0442(9) 0.0017(6) 0.0052(7) 0.0003(7) C006 0.0488(10) 0.0444(8) 0.0394(8) -0.0053(6) 0.0035(7) 0.0014(7) C007 0.0447(9) 0.0462(8) 0.0328(7) 0.0026(6) -0.0001(6) 0.0066(6) C008 0.0507(10) 0.0512(9) 0.0354(8) -0.0064(7) 0.0043(7) 0.0005(7) C009 0.0590(11) 0.0453(9) 0.0547(10) 0.0061(7) -0.0024(8) 0.0028(8) C010 0.0482(9) 0.0475(9) 0.0427(8) 0.0048(6) 0.0044(7) 0.0000(7) C011 0.0541(10) 0.0503(9) 0.0438(9) 0.0029(7) -0.0075(7) -0.0062(7) C012 0.0755(13) 0.0544(10) 0.0539(10) 0.0000(8) 0.0192(9) 0.0004(9) C013 0.0483(10) 0.0631(10) 0.0423(9) -0.0027(7) 0.0047(7) 0.0051(8) C014 0.0626(12) 0.0514(9) 0.0583(10) 0.0023(8) 0.0101(8) -0.0132(8) C015 0.0652(12) 0.0503(9) 0.0654(12) -0.0103(8) 0.0012(9) -0.0120(8) C016 0.0735(13) 0.0667(11) 0.0469(10) 0.0131(8) 0.0093(9) -0.0064(10) C017 0.0799(14) 0.0701(12) 0.0782(14) 0.0079(10) 0.0319(11) 0.0201(11) C018 0.0511(11) 0.0886(14) 0.0627(11) 0.0030(10) 0.0028(9) 0.0241(10) C019 0.0723(13) 0.0648(11) 0.0448(10) -0.0028(8) -0.0139(8) -0.0038(9) C020 0.0852(14) 0.0808(13) 0.0353(9) 0.0039(9) -0.0026(9) 0.0018(11) C021 0.0828(15) 0.0505(10) 0.0780(14) 0.0136(9) 0.0034(11) 0.0160(10) C022 0.1012(17) 0.0719(13) 0.0627(12) -0.0007(10) 0.0261(11) -0.0220(13) C023 0.0715(15) 0.1125(19) 0.0572(12) -0.0001(12) 0.0181(10) -0.0225(13) C024 0.0846(16) 0.0733(13) 0.0770(14) 0.0104(11) 0.0071(11) 0.0379(12) C025 0.0667(15) 0.1100(18) 0.0926(17) -0.0216(13) 0.0250(12) -0.0338(13) C026 0.163(3) 0.0528(12) 0.0892(16) 0.0164(11) 0.0030(16) -0.0232(14) C027 0.0724(15) 0.119(2) 0.0829(16) 0.0051(14) 0.0326(12) 0.0234(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O001 C006 1.4253(19) . ? O001 C007 1.4468(19) . ? O002 C005 1.2201(19) . ? N003 C005 1.356(2) . ? N003 C004 1.443(2) . ? N003 C007 1.4842(19) . ? C004 C011 1.393(2) . ? C004 C010 1.411(2) . ? C005 C006 1.524(2) . ? C006 C008 1.514(2) . ? C006 H006 0.98 . ? C007 C013 1.519(2) . ? C007 C009 1.527(2) . ? C008 C012 1.374(2) . ? C008 C017 1.391(3) . ? C009 C021 1.538(2) . ? C009 H00A 0.97 . ? C009 H00B 0.97 . ? C010 C016 1.406(2) . ? C010 C014 1.551(2) . ? C011 C019 1.373(2) . ? C011 H011 0.93 . ? C012 C022 1.391(3) . ? C012 H012 0.93 . ? C013 C018 1.524(2) . ? C013 H01A 0.97 . ? C013 H01B 0.97 . ? C014 C015 1.531(3) . ? C014 C025 1.550(3) . ? C014 C026 1.551(3) . ? C015 H01C 0.96 . ? C015 H01D 0.96 . ? C015 H01E 0.96 . ? C016 C020 1.376(3) . ? C016 H016 0.93 . ? C017 C027 1.394(3) . ? C017 H017 0.93 . ? C018 C024 1.519(3) . ? C018 H01F 0.97 . ? C018 H01G 0.97 . ? C019 C020 1.372(3) . ? C019 H019 0.93 . ? C020 H020 0.93 . ? C021 C024 1.522(3) . ? C021 H02A 0.97 . ? C021 H02B 0.97 . ? C022 C023 1.370(3) . ? C022 H022 0.93 . ? C023 C027 1.371(4) . ? C023 H023 0.93 . ? C024 H02C 0.97 . ? C024 H02D 0.97 . ? C025 H02E 0.96 . ? C025 H02F 0.96 . ? C025 H02G 0.96 . ? C026 H02H 0.96 . ? C026 H02I 0.96 . ? C026 H02J 0.96 . ? C027 H027 0.93 . ? 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 C006 O001 C007 111.28(11) . . ? C005 N003 C004 122.81(12) . . ? C005 N003 C007 112.00(12) . . ? C004 N003 C007 124.04(11) . . ? C011 C004 C010 120.91(14) . . ? C011 C004 N003 115.68(13) . . ? C010 C004 N003 123.40(13) . . ? O002 C005 N003 127.29(14) . . ? O002 C005 C006 126.25(14) . . ? N003 C005 C006 106.34(13) . . ? O001 C006 C008 113.79(13) . . ? O001 C006 C005 105.08(12) . . ? C008 C006 C005 115.19(13) . . ? O001 C006 H006 107.5 . . ? C008 C006 H006 107.5 . . ? C005 C006 H006 107.5 . . ? O001 C007 N003 102.16(11) . . ? O001 C007 C013 107.83(12) . . ? N003 C007 C013 113.24(13) . . ? O001 C007 C009 109.54(12) . . ? N003 C007 C009 112.60(13) . . ? C013 C007 C009 110.96(13) . . ? C012 C008 C017 118.19(17) . . ? C012 C008 C006 122.32(15) . . ? C017 C008 C006 119.48(16) . . ? C007 C009 C021 111.57(15) . . ? C007 C009 H00A 109.3 . . ? C021 C009 H00A 109.3 . . ? C007 C009 H00B 109.3 . . ? C021 C009 H00B 109.3 . . ? H00A C009 H00B 108 . . ? C016 C010 C004 114.74(15) . . ? C016 C010 C014 116.33(14) . . ? C004 C010 C014 128.91(15) . . ? C019 C011 C004 121.97(16) . . ? C019 C011 H011 119 . . ? C004 C011 H011 119 . . ? C008 C012 C022 120.93(18) . . ? C008 C012 H012 119.5 . . ? C022 C012 H012 119.5 . . ? C007 C013 C018 111.43(15) . . ? C007 C013 H01A 109.3 . . ? C018 C013 H01A 109.3 . . ? C007 C013 H01B 109.3 . . ? C018 C013 H01B 109.3 . . ? H01A C013 H01B 108 . . ? C015 C014 C025 108.07(17) . . ? C015 C014 C026 105.64(17) . . ? C025 C014 C026 109.74(19) . . ? C015 C014 C010 116.61(14) . . ? C025 C014 C010 107.90(16) . . ? C026 C014 C010 108.76(17) . . ? C014 C015 H01C 109.5 . . ? C014 C015 H01D 109.5 . . ? H01C C015 H01D 109.5 . . ? C014 C015 H01E 109.5 . . ? H01C C015 H01E 109.5 . . ? H01D C015 H01E 109.5 . . ? C020 C016 C010 123.76(16) . . ? C020 C016 H016 118.1 . . ? C010 C016 H016 118.1 . . ? C008 C017 C027 120.6(2) . . ? C008 C017 H017 119.7 . . ? C027 C017 H017 119.7 . . ? C024 C018 C013 111.37(16) . . ? C024 C018 H01F 109.4 . . ? C013 C018 H01F 109.4 . . ? C024 C018 H01G 109.4 . . ? C013 C018 H01G 109.4 . . ? H01F C018 H01G 108 . . ? C020 C019 C011 118.43(16) . . ? C020 C019 H019 120.8 . . ? C011 C019 H019 120.8 . . ? C019 C020 C016 120.12(17) . . ? C019 C020 H020 119.9 . . ? C016 C020 H020 119.9 . . ? C024 C021 C009 110.94(16) . . ? C024 C021 H02A 109.5 . . ? C009 C021 H02A 109.5 . . ? C024 C021 H02B 109.5 . . ? C009 C021 H02B 109.5 . . ? H02A C021 H02B 108 . . ? C023 C022 C012 120.6(2) . . ? C023 C022 H022 119.7 . . ? C012 C022 H022 119.7 . . ? C022 C023 C027 119.4(2) . . ? C022 C023 H023 120.3 . . ? C027 C023 H023 120.3 . . ? C018 C024 C021 110.41(16) . . ? C018 C024 H02C 109.6 . . ? C021 C024 H02C 109.6 . . ? C018 C024 H02D 109.6 . . ? C021 C024 H02D 109.6 . . ? H02C C024 H02D 108.1 . . ? C014 C025 H02E 109.5 . . ? C014 C025 H02F 109.5 . . ? H02E C025 H02F 109.5 . . ? C014 C025 H02G 109.5 . . ? H02E C025 H02G 109.5 . . ? H02F C025 H02G 109.5 . . ? C014 C026 H02H 109.5 . . ? C014 C026 H02I 109.5 . . ? H02H C026 H02I 109.5 . . ? C014 C026 H02J 109.5 . . ? H02H C026 H02J 109.5 . . ? H02I C026 H02J 109.5 . . ? C023 C027 C017 120.3(2) . . ? C023 C027 H027 119.9 . . ? C017 C027 H027 119.9 . . ? #===END data_cis-2d _database_code_depnum_ccdc_archive 'CCDC 759993' #TrackingRef 'X-ray-revised.cif.txt' _audit_creation_date 2009-11-24T14:48:32-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C24 H29 N O2' _chemical_formula_weight 363.48 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.7836(18) _cell_length_b 10.399(2) _cell_length_c 22.804(5) _cell_angle_alpha 90 _cell_angle_beta 99.457(3) _cell_angle_gamma 90 _cell_volume 2054.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4987 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 26.65 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.175 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.6511 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_process_details 'SADABS (SAINT 6.45A)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0489 _diffrn_reflns_av_unetI/netI 0.0425 _diffrn_reflns_number 18137 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 27.02 _diffrn_reflns_theta_full 27.02 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 4488 _reflns_number_gt 3072 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'SMART 1K' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0872P)^2^+0.1620P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.023(3) _refine_ls_number_reflns 4488 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.162 _refine_ls_wR_factor_gt 0.1386 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.33 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.096 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O001 O 0.36679(14) 0.34212(11) 0.51602(5) 0.0601(4) Uani 1 1 d . . . O002 O 0.52901(13) 0.48060(11) 0.65247(5) 0.0553(3) Uani 1 1 d . . . N003 N 0.49938(13) 0.28544(11) 0.60796(5) 0.0404(3) Uani 1 1 d . . . C004 C 0.50215(15) 0.14900(14) 0.59785(6) 0.0396(3) Uani 1 1 d . . . C005 C 0.38149(16) 0.06626(14) 0.60697(6) 0.0421(4) Uani 1 1 d . . . C006 C 0.22681(17) 0.09992(16) 0.62740(7) 0.0513(4) Uani 1 1 d . . . C007 C 0.59399(16) 0.35466(14) 0.65803(6) 0.0418(4) Uani 1 1 d . . . C008 C 0.43393(16) 0.36871(15) 0.56579(7) 0.0446(4) Uani 1 1 d . . . C009 C 0.45711(19) 0.50230(15) 0.59263(7) 0.0491(4) Uani 1 1 d . . . H009 H 0.5259 0.5523 0.5716 0.059 Uiso 1 1 calc R . . C010 C 0.40454(19) -0.06389(16) 0.59529(7) 0.0523(4) Uani 1 1 d . . . H010 H 0.3286 -0.1223 0.6015 0.063 Uiso 1 1 calc R . . C011 C 0.76370(17) 0.36072(18) 0.65116(8) 0.0559(4) Uani 1 1 d . . . H01A H 0.7728 0.4017 0.6137 0.067 Uiso 1 1 calc R . . H01B H 0.8043 0.2741 0.6504 0.067 Uiso 1 1 calc R . . C012 C 0.63018(17) 0.10144(16) 0.57572(7) 0.0491(4) Uani 1 1 d . . . H012 H 0.7063 0.1585 0.5683 0.059 Uiso 1 1 calc R . . C013 C 0.30505(19) 0.57213(15) 0.59038(7) 0.0506(4) Uani 1 1 d . . . C014 C 0.5768(2) 0.30117(19) 0.71831(7) 0.0587(5) Uani 1 1 d . . . H01C H 0.6074 0.2114 0.7204 0.07 Uiso 1 1 calc R . . H01D H 0.4692 0.3056 0.7231 0.07 Uiso 1 1 calc R . . C015 C 0.64677(19) -0.02700(17) 0.56462(8) 0.0559(4) Uani 1 1 d . . . H015 H 0.7333 -0.0571 0.5503 0.067 Uiso 1 1 calc R . . C016 C 0.18899(18) 0.24251(18) 0.63269(10) 0.0668(5) Uani 1 1 d . . . H01E H 0.1881 0.2838 0.595 0.1 Uiso 1 1 calc R . . H01F H 0.2657 0.282 0.662 0.1 Uiso 1 1 calc R . . H01G H 0.0894 0.2512 0.6444 0.1 Uiso 1 1 calc R . . C017 C 0.8585(2) 0.4358(2) 0.70203(9) 0.0713(6) Uani 1 1 d . . . H01H H 0.9663 0.4346 0.6974 0.086 Uiso 1 1 calc R . . H01I H 0.8244 0.5246 0.7004 0.086 Uiso 1 1 calc R . . C018 C 0.2476(2) 0.60379(18) 0.64097(9) 0.0691(5) Uani 1 1 d . . . H018 H 0.3055 0.5865 0.6781 0.083 Uiso 1 1 calc R . . C019 C 0.5333(2) -0.11008(17) 0.57510(8) 0.0576(5) Uani 1 1 d . . . H019 H 0.5432 -0.1977 0.5686 0.069 Uiso 1 1 calc R . . C020 C 0.6744(2) 0.3748(2) 0.76878(8) 0.0767(6) Uani 1 1 d . . . H02A H 0.6349 0.4617 0.77 0.092 Uiso 1 1 calc R . . H02B H 0.6663 0.3335 0.8063 0.092 Uiso 1 1 calc R . . C021 C 0.8425(2) 0.3799(2) 0.76116(9) 0.0841(7) Uani 1 1 d . . . H02C H 0.9 0.4319 0.7925 0.101 Uiso 1 1 calc R . . H02D H 0.8855 0.2938 0.7644 0.101 Uiso 1 1 calc R . . C022 C 0.0946(2) 0.0455(2) 0.58135(11) 0.0825(7) Uani 1 1 d . . . H02E H 0.1116 -0.0446 0.5758 0.124 Uiso 1 1 calc R . . H02F H 0.0916 0.0897 0.5442 0.124 Uiso 1 1 calc R . . H02G H -0.0017 0.0573 0.5953 0.124 Uiso 1 1 calc R . . C023 C 0.0169(3) 0.6854(2) 0.58319(17) 0.1033(9) Uani 1 1 d . . . H023 H -0.0809 0.7213 0.5808 0.124 Uiso 1 1 calc R . . C024 C 0.2255(3) 0.0364(3) 0.68798(10) 0.0864(7) Uani 1 1 d . . . H02H H 0.2483 -0.0535 0.6855 0.13 Uiso 1 1 calc R . . H02I H 0.1254 0.0466 0.6991 0.13 Uiso 1 1 calc R . . H02J H 0.3019 0.0763 0.7173 0.13 Uiso 1 1 calc R . . C025 C 0.2199(3) 0.6017(2) 0.53650(10) 0.0870(7) Uani 1 1 d . . . H025 H 0.2598 0.5851 0.5019 0.104 Uiso 1 1 calc R . . C026 C 0.1046(3) 0.6610(2) 0.63719(13) 0.0921(8) Uani 1 1 d . . . H026 H 0.0677 0.6831 0.6718 0.11 Uiso 1 1 calc R . . C027 C 0.0748(4) 0.6562(3) 0.53268(15) 0.1148(11) Uani 1 1 d . . . H027 H 0.0165 0.673 0.4956 0.138 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 O001 0.0735(8) 0.0612(8) 0.0416(7) -0.0059(5) -0.0019(5) 0.0139(6) O002 0.0658(7) 0.0473(7) 0.0488(7) -0.0100(5) -0.0026(5) 0.0061(5) N003 0.0394(6) 0.0400(7) 0.0401(7) -0.0038(5) 0.0017(5) -0.0004(5) C004 0.0382(7) 0.0408(8) 0.0373(8) -0.0020(6) -0.0014(5) 0.0028(6) C005 0.0417(7) 0.0440(8) 0.0378(8) -0.0021(6) -0.0018(6) 0.0001(6) C006 0.0374(7) 0.0587(10) 0.0571(10) -0.0033(8) 0.0054(7) -0.0062(7) C007 0.0397(7) 0.0427(8) 0.0421(8) -0.0044(6) 0.0035(6) -0.0027(6) C008 0.0469(8) 0.0475(9) 0.0395(8) -0.0017(7) 0.0077(6) 0.0052(6) C009 0.0597(9) 0.0440(9) 0.0442(9) 0.0029(7) 0.0097(7) 0.0015(7) C010 0.0584(9) 0.0445(9) 0.0511(9) -0.0023(7) 0.0004(7) -0.0059(7) C011 0.0422(8) 0.0680(11) 0.0574(10) -0.0117(8) 0.0081(7) -0.0108(7) C012 0.0413(8) 0.0544(10) 0.0511(9) -0.0056(7) 0.0060(6) 0.0023(7) C013 0.0638(10) 0.0345(8) 0.0534(10) 0.0011(7) 0.0092(8) 0.0042(7) C014 0.0561(9) 0.0739(12) 0.0438(9) 0.0030(8) 0.0010(7) -0.0157(8) C015 0.0523(9) 0.0597(11) 0.0543(10) -0.0088(8) 0.0051(7) 0.0152(8) C016 0.0380(8) 0.0725(12) 0.0914(14) -0.0161(10) 0.0150(8) 0.0023(8) C017 0.0477(9) 0.0919(15) 0.0727(13) -0.0207(11) 0.0057(8) -0.0216(9) C018 0.0795(13) 0.0613(12) 0.0718(13) 0.0114(10) 0.0282(10) 0.0165(10) C019 0.0691(11) 0.0438(9) 0.0564(10) -0.0086(7) -0.0008(8) 0.0096(8) C020 0.0749(12) 0.1089(17) 0.0435(10) -0.0040(10) 0.0012(9) -0.0275(11) C021 0.0650(12) 0.1122(18) 0.0657(13) -0.0093(12) -0.0170(10) -0.0192(11) C022 0.0457(10) 0.0848(15) 0.1099(18) -0.0239(13) -0.0080(10) -0.0082(9) C023 0.0686(14) 0.0608(14) 0.177(3) 0.0025(17) 0.0096(17) 0.0149(11) C024 0.0755(13) 0.1119(19) 0.0790(15) 0.0165(13) 0.0341(11) 0.0039(12) C025 0.1131(18) 0.0750(14) 0.0648(13) -0.0023(11) -0.0094(12) 0.0407(13) C026 0.0890(16) 0.0737(15) 0.126(2) 0.0205(14) 0.0557(16) 0.0250(12) C027 0.120(2) 0.0811(18) 0.121(2) -0.0143(15) -0.0436(18) 0.0448(15) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O001 C008 1.2216(17) . ? O002 C009 1.4243(19) . ? O002 C007 1.4258(18) . ? N003 C008 1.3504(19) . ? N003 C004 1.4382(19) . ? N003 C007 1.4836(17) . ? C004 C012 1.397(2) . ? C004 C005 1.407(2) . ? C005 C010 1.400(2) . ? C005 C006 1.547(2) . ? C006 C016 1.529(2) . ? C006 C024 1.533(3) . ? C006 C022 1.540(2) . ? C007 C014 1.513(2) . ? C007 C011 1.526(2) . ? C008 C009 1.518(2) . ? C009 C013 1.514(2) . ? C009 H009 0.98 . ? C010 C019 1.376(2) . ? C010 H010 0.93 . ? C011 C017 1.527(2) . ? C011 H01A 0.97 . ? C011 H01B 0.97 . ? C012 C015 1.372(2) . ? C012 H012 0.93 . ? C013 C025 1.365(3) . ? C013 C018 1.373(3) . ? C014 C020 1.524(2) . ? C014 H01C 0.97 . ? C014 H01D 0.97 . ? C015 C019 1.370(3) . ? C015 H015 0.93 . ? C016 H01E 0.96 . ? C016 H01F 0.96 . ? C016 H01G 0.96 . ? C017 C021 1.496(3) . ? C017 H01H 0.97 . ? C017 H01I 0.97 . ? C018 C026 1.379(3) . ? C018 H018 0.93 . ? C019 H019 0.93 . ? C020 C021 1.516(3) . ? C020 H02A 0.97 . ? C020 H02B 0.97 . ? C021 H02C 0.97 . ? C021 H02D 0.97 . ? C022 H02E 0.96 . ? C022 H02F 0.96 . ? C022 H02G 0.96 . ? C023 C026 1.365(4) . ? C023 C027 1.367(4) . ? C023 H023 0.93 . ? C024 H02H 0.96 . ? C024 H02I 0.96 . ? C024 H02J 0.96 . ? C025 C027 1.384(4) . ? C025 H025 0.93 . ? C026 H026 0.93 . ? C027 H027 0.93 . ? 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 C009 O002 C007 109.80(11) . . ? C008 N003 C004 122.34(12) . . ? C008 N003 C007 110.86(12) . . ? C004 N003 C007 125.45(11) . . ? C012 C004 C005 120.51(14) . . ? C012 C004 N003 116.30(13) . . ? C005 C004 N003 123.14(12) . . ? C010 C005 C004 115.27(14) . . ? C010 C005 C006 115.94(14) . . ? C004 C005 C006 128.78(14) . . ? C016 C006 C024 108.24(16) . . ? C016 C006 C022 105.15(15) . . ? C024 C006 C022 109.85(17) . . ? C016 C006 C005 117.14(13) . . ? C024 C006 C005 108.11(14) . . ? C022 C006 C005 108.21(14) . . ? O002 C007 N003 102.23(10) . . ? O002 C007 C014 108.67(13) . . ? N003 C007 C014 113.19(12) . . ? O002 C007 C011 109.67(13) . . ? N003 C007 C011 111.97(12) . . ? C014 C007 C011 110.71(13) . . ? O001 C008 N003 126.90(15) . . ? O001 C008 C009 126.44(14) . . ? N003 C008 C009 106.64(12) . . ? O002 C009 C013 111.00(13) . . ? O002 C009 C008 104.50(12) . . ? C013 C009 C008 111.48(13) . . ? O002 C009 H009 109.9 . . ? C013 C009 H009 109.9 . . ? C008 C009 H009 109.9 . . ? C019 C010 C005 123.61(16) . . ? C019 C010 H010 118.2 . . ? C005 C010 H010 118.2 . . ? C007 C011 C017 111.29(14) . . ? C007 C011 H01A 109.4 . . ? C017 C011 H01A 109.4 . . ? C007 C011 H01B 109.4 . . ? C017 C011 H01B 109.4 . . ? H01A C011 H01B 108 . . ? C015 C012 C004 121.86(15) . . ? C015 C012 H012 119.1 . . ? C004 C012 H012 119.1 . . ? C025 C013 C018 118.64(18) . . ? C025 C013 C009 119.28(16) . . ? C018 C013 C009 122.06(15) . . ? C007 C014 C020 111.94(15) . . ? C007 C014 H01C 109.2 . . ? C020 C014 H01C 109.2 . . ? C007 C014 H01D 109.2 . . ? C020 C014 H01D 109.2 . . ? H01C C014 H01D 107.9 . . ? C019 C015 C012 118.66(16) . . ? C019 C015 H015 120.7 . . ? C012 C015 H015 120.7 . . ? C006 C016 H01E 109.5 . . ? C006 C016 H01F 109.5 . . ? H01E C016 H01F 109.5 . . ? C006 C016 H01G 109.5 . . ? H01E C016 H01G 109.5 . . ? H01F C016 H01G 109.5 . . ? C021 C017 C011 111.48(16) . . ? C021 C017 H01H 109.3 . . ? C011 C017 H01H 109.3 . . ? C021 C017 H01I 109.3 . . ? C011 C017 H01I 109.3 . . ? H01H C017 H01I 108 . . ? C013 C018 C026 120.5(2) . . ? C013 C018 H018 119.7 . . ? C026 C018 H018 119.7 . . ? C015 C019 C010 120.00(16) . . ? C015 C019 H019 120 . . ? C010 C019 H019 120 . . ? C021 C020 C014 111.67(17) . . ? C021 C020 H02A 109.3 . . ? C014 C020 H02A 109.3 . . ? C021 C020 H02B 109.3 . . ? C014 C020 H02B 109.3 . . ? H02A C020 H02B 107.9 . . ? C017 C021 C020 110.75(16) . . ? C017 C021 H02C 109.5 . . ? C020 C021 H02C 109.5 . . ? C017 C021 H02D 109.5 . . ? C020 C021 H02D 109.5 . . ? H02C C021 H02D 108.1 . . ? C006 C022 H02E 109.5 . . ? C006 C022 H02F 109.5 . . ? H02E C022 H02F 109.5 . . ? C006 C022 H02G 109.5 . . ? H02E C022 H02G 109.5 . . ? H02F C022 H02G 109.5 . . ? C026 C023 C027 119.0(2) . . ? C026 C023 H023 120.5 . . ? C027 C023 H023 120.5 . . ? C006 C024 H02H 109.5 . . ? C006 C024 H02I 109.5 . . ? H02H C024 H02I 109.5 . . ? C006 C024 H02J 109.5 . . ? H02H C024 H02J 109.5 . . ? H02I C024 H02J 109.5 . . ? C013 C025 C027 120.8(2) . . ? C013 C025 H025 119.6 . . ? C027 C025 H025 119.6 . . ? C023 C026 C018 120.7(2) . . ? C023 C026 H026 119.7 . . ? C018 C026 H026 119.7 . . ? C023 C027 C025 120.3(2) . . ? C023 C027 H027 119.9 . . ? C025 C027 H027 119.9 . . ? # END of CIF