Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_jb19 _database_code_CSD 162511 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'M.-L. Bennasar' 'E. Zulaica' 'Y. Alonso' 'I. Mata' 'E. Molins' 'J. Bosch' _publ_contact_author_name 'Dr M-Lluisa Bennasar' _publ_contact_author_address ; Dr M-Lluisa Bennasar Laboratory of Organic Chemistry University of Barcelona Faculty of Pharmacy Barcelona 08028 SPAIN ; _publ_contact_author_email 'BENNASAR@FARMACIA.FAR.UB.ES' _audit_creation_date 2001-03-03T16:01:35-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic _publ_requested_category FO #--------------------------------------------------------------------------- # # CHEMICAL INFORMATION # #--------------------------------------------------------------------------- # _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C25 H29 N3 O3' _chemical_formula_structural 'C25 N3 O3 H29' _chemical_formula_sum 'C25 H29 N3 O3' _chemical_formula_weight 419.51 _chemical_compound_source 'synthesis as described' #--------------------------------------------------------------------------- -# # UNIT CELL INFORMATION # #--------------------------------------------------------------------------- -# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.4175(10) _cell_length_b 8.8264(10) _cell_length_c 12.670(2) _cell_angle_alpha 90 _cell_angle_beta 106.917(12) _cell_angle_gamma 90 _cell_volume 1114.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 15 _cell_measurement_theta_min 11.97 _cell_measurement_theta_max 12.6 _cell_measurement_wavelength 0.71073 #--------------------------------------------------------------------------- -# # CRYSTAL INFORMATION # #--------------------------------------------------------------------------- -# _exptl_crystal_description prism _exptl_crystal_colour white _exptl_crystal_size_max 0.99 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.25 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_special_details ; ? ; #--------------------------------------------------------------------------- -# # ABSORPTION CORRECTION # #--------------------------------------------------------------------------- -# _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_factor_muR 0.01 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 7 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.9647 _exptl_absorpt_correction_T_max 0.9895 _exptl_absorpt_correction_T_ave 0.9823 #--------------------------------------------------------------------------- -# # DATA COLLECTION # #--------------------------------------------------------------------------- -# _diffrn_source 'Enraf Nonius FR590' _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_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 0.45358E-1 _diffrn_orient_matrix_ub_12 0.21805E-1 _diffrn_orient_matrix_ub_13 0.79599E-1 _diffrn_orient_matrix_ub_21 0.87007E-1 _diffrn_orient_matrix_ub_22 0.15164E-1 _diffrn_orient_matrix_ub_23 -0.17041E-1 _diffrn_orient_matrix_ub_31 -0.20926E-1 _diffrn_orient_matrix_ub_32 0.110147 _diffrn_orient_matrix_ub_33 -0.0134 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_standards_decay_corr_max 1 _diffrn_standards_decay_corr_min 1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 2 -7 4 4 0 5 -3 -3 _diffrn_reflns_number 3961 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_unetI/netI 0.0252 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 30.4 _diffrn_reflns_theta_full 30.4 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3565 _reflns_number_gt 2818 _reflns_threshold_expression >2sigma(I) #--------------------------------------------------------------------------- -# # COMPUTER PROGRAMS USED # #--------------------------------------------------------------------------- -# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #--------------------------------------------------------------------------- -# # 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^)+(0.0701P)^2^+0.0572P] 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_number_reflns 3565 _refine_ls_number_parameters 283 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.066 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.112 _refine_ls_wR_factor_gt 0.1013 _refine_ls_goodness_of_fit_ref 1.02 _refine_ls_restrained_S_all 1.02 _refine_ls_shift/su_max 0.031 _refine_ls_shift/su_mean 0.001 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(13) _refine_diff_density_max 0.207 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.04 #--------------------------------------------------------------------------- -# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #--------------------------------------------------------------------------- -# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O1 O -0.39782(17) 0.2488(2) 0.69943(17) 0.0738(5) Uani 1 1 d . . . O2 O 0.04105(13) 0.35881(18) 0.70343(12) 0.0521(3) Uani 1 1 d . . . O3 O 0.23233(18) 0.4445(2) 0.48690(15) 0.0660(4) Uani 1 1 d . . . N1 N -0.21528(17) 0.74849(18) 0.79414(14) 0.0466(4) Uani 1 1 d . . . N2 N -0.54981(14) 0.42851(18) 0.80472(12) 0.0414(3) Uani 1 1 d . . . N3 N -0.07984(16) 0.4968(2) 0.55778(13) 0.0476(4) Uani 1 1 d . . . C1 C -0.16634(18) 0.6699(2) 0.72236(16) 0.0434(4) Uani 1 1 d . . . H1 H -0.1685 0.7166 0.6561 0.052 Uiso 1 1 calc R . . C2 C -0.11427(17) 0.5275(2) 0.74032(15) 0.0414(4) Uani 1 1 d . . . C3 C -0.10148(16) 0.4482(2) 0.84876(15) 0.0422(4) Uani 1 1 d . . . H3 H -0.0085 0.4134 0.8774 0.051 Uiso 1 1 calc R . . C4 C -0.12740(17) 0.5558(2) 0.93280(15) 0.0424(4) Uani 1 1 d . . . C5 C -0.23930(17) 0.6670(2) 0.88771(14) 0.0396(3) Uani 1 1 d . . . H5 H -0.236 0.7416 0.9457 0.047 Uiso 1 1 calc R . . C6 C -0.37558(16) 0.5920(2) 0.85906(13) 0.0350(3) Uani 1 1 d . . . C7 C -0.41400(15) 0.4493(2) 0.81544(13) 0.0366(3) Uani 1 1 d . . . C8 C -0.33975(19) 0.3312(2) 0.77489(15) 0.0430(4) Uani 1 1 d . . . C9 C -0.19203(18) 0.3066(2) 0.83090(16) 0.0429(4) Uani 1 1 d . . . H9A H -0.1587 0.2344 0.7874 0.051 Uiso 1 1 calc R . . H9B H -0.1826 0.2605 0.9023 0.051 Uiso 1 1 calc R . . C10 C -0.49219(17) 0.6627(2) 0.87477(13) 0.0388(3) Uani 1 1 d . . . C11 C -0.5180(2) 0.8057(2) 0.91298(15) 0.0496(4) Uani 1 1 d . . . H11 H -0.4501 0.8775 0.9349 0.06 Uiso 1 1 calc R . . C12 C -0.6459(2) 0.8375(3) 0.91735(17) 0.0607(6) Uani 1 1 d . . . H12 H -0.6645 0.9323 0.9413 0.073 Uiso 1 1 calc R . . C13 C -0.7479(2) 0.7294(4) 0.88637(18) 0.0629(6) Uani 1 1 d . . . H13 H -0.8329 0.7539 0.891 0.075 Uiso 1 1 calc R . . C14 C -0.7266(2) 0.5875(3) 0.84916(16) 0.0541(5) Uani 1 1 d . . . H14 H -0.7948 0.5158 0.8296 0.065 Uiso 1 1 calc R . . C15 C -0.59738(17) 0.5563(2) 0.84218(14) 0.0419(4) Uani 1 1 d . . . C16 C -0.6260(2) 0.2884(3) 0.7777(2) 0.0605(6) Uani 1 1 d . . . H16A H -0.7113 0.3005 0.7916 0.091 Uiso 1 1 calc R . . H16B H -0.5772 0.2076 0.8225 0.091 Uiso 1 1 calc R . . H16C H -0.6399 0.2648 0.7013 0.091 Uiso 1 1 calc R . . C17 C -0.0597(2) 0.5523(3) 1.03904(18) 0.0566(5) Uani 1 1 d . . . H17A H -0.081 0.6198 1.0878 0.068 Uiso 1 1 calc R . . H17B H 0.0091 0.4824 1.0648 0.068 Uiso 1 1 calc R . . C18 C -0.2872(3) 0.8891(3) 0.7615(2) 0.0617(6) Uani 1 1 d . . . H18A H -0.3804 0.8678 0.7271 0.093 Uiso 1 1 calc R . . H18B H -0.2509 0.9415 0.7103 0.093 Uiso 1 1 calc R . . H18C H -0.2781 0.9513 0.8254 0.093 Uiso 1 1 calc R . . C19 C -0.04785(17) 0.4540(2) 0.66622(15) 0.0420(4) Uani 1 1 d . . . C20 C -0.2159(2) 0.5344(3) 0.48770(19) 0.0589(5) Uani 1 1 d . . . H20A H -0.2259 0.6425 0.4743 0.071 Uiso 1 1 calc R . . H20B H -0.2837 0.5001 0.5209 0.071 Uiso 1 1 calc R . . C21 C -0.2245(3) 0.4477(3) 0.38153(19) 0.0691(7) Uani 1 1 d . . . H21A H -0.2514 0.3434 0.3867 0.083 Uiso 1 1 calc R . . H21B H -0.2876 0.4953 0.3185 0.083 Uiso 1 1 calc R . . C22 C -0.0830(3) 0.4566(4) 0.37300(19) 0.0725(7) Uani 1 1 d . . . H22A H -0.0672 0.5533 0.3426 0.087 Uiso 1 1 calc R . . H22B H -0.0663 0.376 0.3266 0.087 Uiso 1 1 calc R . . C23 C 0.0060(2) 0.4389(2) 0.49142(19) 0.0513(4) Uani 1 1 d . . . H23 H 0.0255 0.3314 0.5077 0.062 Uiso 1 1 calc R . . C24 C 0.1357(2) 0.5277(3) 0.5198(2) 0.0554(5) Uani 1 1 d . . . H24A H 0.1212 0.6248 0.4823 0.066 Uiso 1 1 calc R . . H24B H 0.1668 0.5462 0.5987 0.066 Uiso 1 1 calc R . . C25 C 0.3589(3) 0.5173(5) 0.5164(2) 0.0777(8) Uani 1 1 d . . . H25A H 0.3848 0.5414 0.5936 0.117 Uiso 1 1 calc R . . H25B H 0.3532 0.6088 0.4743 0.117 Uiso 1 1 calc R . . H25C H 0.4245 0.4511 0.5012 0.117 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 O1 0.0618(9) 0.0653(11) 0.0851(11) -0.0392(10) 0.0069(8) 0.0072(9) O2 0.0424(6) 0.0519(8) 0.0617(8) 0.0025(7) 0.0147(6) 0.0101(6) O3 0.0692(9) 0.0603(10) 0.0786(10) -0.0118(9) 0.0374(8) -0.0007(9) N1 0.0582(9) 0.0315(7) 0.0573(9) 0.0065(7) 0.0284(7) 0.0007(7) N2 0.0357(6) 0.0385(7) 0.0478(7) -0.0066(6) 0.0088(5) -0.0039(6) N3 0.0497(8) 0.0454(8) 0.0492(8) 0.0000(7) 0.0167(7) 0.0040(7) C1 0.0480(8) 0.0360(8) 0.0500(9) 0.0062(8) 0.0203(7) -0.0030(7) C2 0.0376(7) 0.0383(8) 0.0504(9) 0.0049(7) 0.0162(7) -0.0001(7) C3 0.0345(7) 0.0402(8) 0.0522(9) 0.0066(8) 0.0130(6) 0.0016(7) C4 0.0371(7) 0.0405(9) 0.0488(8) 0.0029(8) 0.0111(6) -0.0076(7) C5 0.0451(8) 0.0329(8) 0.0419(8) -0.0009(7) 0.0146(6) -0.0043(7) C6 0.0380(7) 0.0323(7) 0.0347(7) 0.0006(6) 0.0107(6) 0.0001(6) C7 0.0364(7) 0.0337(8) 0.0383(7) -0.0015(7) 0.0089(6) -0.0005(6) C8 0.0459(8) 0.0335(8) 0.0497(9) -0.0028(7) 0.0140(7) 0.0028(7) C9 0.0423(8) 0.0327(8) 0.0551(10) 0.0067(7) 0.0167(7) 0.0052(7) C10 0.0428(8) 0.0404(8) 0.0335(7) -0.0026(7) 0.0113(6) 0.0037(7) C11 0.0611(11) 0.0448(10) 0.0442(9) -0.0100(8) 0.0175(8) 0.0044(9) C12 0.0707(13) 0.0640(14) 0.0506(10) -0.0140(10) 0.0225(10) 0.0207(12) C13 0.0525(11) 0.0862(18) 0.0530(11) -0.0078(12) 0.0201(9) 0.0186(12) C14 0.0415(9) 0.0729(14) 0.0477(10) -0.0072(10) 0.0129(7) 0.0028(9) C15 0.0397(8) 0.0484(10) 0.0365(7) -0.0036(7) 0.0095(6) 0.0010(7) C16 0.0486(10) 0.0460(11) 0.0834(15) -0.0114(11) 0.0133(10) -0.0129(9) C17 0.0476(9) 0.0608(13) 0.0546(10) 0.0005(10) 0.0042(8) -0.0110(9) C18 0.0850(15) 0.0365(9) 0.0728(14) 0.0118(10) 0.0375(12) 0.0111(10) C19 0.0366(7) 0.0383(8) 0.0517(9) -0.0004(7) 0.0140(6) -0.0036(7) C20 0.0634(12) 0.0477(11) 0.0585(11) 0.0046(10) 0.0068(9) 0.0120(10) C21 0.0833(16) 0.0478(12) 0.0608(12) -0.0019(11) -0.0034(11) 0.0086(13) C22 0.0977(18) 0.0657(16) 0.0548(12) -0.0116(12) 0.0236(12) -0.0020(15) C23 0.0638(10) 0.0385(9) 0.0571(10) -0.0078(9) 0.0266(8) -0.0036(9) C24 0.0687(12) 0.0422(10) 0.0654(11) -0.0094(9) 0.0353(10) -0.0063(9) C25 0.0675(14) 0.100(2) 0.0707(14) 0.0008(16) 0.0284(12) -0.0075(16) #--------------------------------------------------------------------------- # 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 O1 C8 1.213(3) . ? O2 C19 1.238(2) . ? O3 C24 1.404(3) . ? O3 C25 1.416(3) . ? N1 C1 1.356(3) . ? N1 C18 1.447(3) . ? N1 C5 1.469(2) . ? N2 C15 1.371(2) . ? N2 C7 1.394(2) . ? N2 C16 1.455(3) . ? N3 C19 1.369(3) . ? N3 C20 1.475(3) . ? N3 C23 1.485(3) . ? C1 C2 1.361(3) . ? C2 C19 1.469(3) . ? C2 C3 1.513(2) . ? C3 C4 1.509(3) . ? C3 C9 1.543(3) . ? C4 C17 1.326(3) . ? C4 C5 1.503(3) . ? C5 C6 1.512(2) . ? C6 C7 1.387(2) . ? C6 C10 1.430(2) . ? C7 C8 1.477(2) . ? C8 C9 1.511(3) . ? C10 C11 1.406(3) . ? C10 C15 1.410(3) . ? C11 C12 1.378(3) . ? C12 C13 1.397(4) . ? C13 C14 1.378(4) . ? C14 C15 1.402(3) . ? C20 C21 1.527(3) . ? C21 C22 1.511(4) . ? C22 C23 1.525(3) . ? C23 C24 1.513(3) . ? 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 C24 O3 C25 112.2(2) . . ? C1 N1 C18 120.79(18) . . ? C1 N1 C5 118.44(15) . . ? C18 N1 C5 117.08(16) . . ? C15 N2 C7 108.48(15) . . ? C15 N2 C16 123.56(16) . . ? C7 N2 C16 127.14(16) . . ? C19 N3 C20 125.24(17) . . ? C19 N3 C23 117.56(17) . . ? C20 N3 C23 111.59(18) . . ? N1 C1 C2 124.72(17) . . ? C1 C2 C19 122.65(17) . . ? C1 C2 C3 120.29(17) . . ? C19 C2 C3 116.27(16) . . ? C4 C3 C2 111.30(16) . . ? C4 C3 C9 112.72(14) . . ? C2 C3 C9 110.69(15) . . ? C17 C4 C5 121.71(19) . . ? C17 C4 C3 123.39(19) . . ? C5 C4 C3 114.88(14) . . ? N1 C5 C4 109.32(14) . . ? N1 C5 C6 112.90(14) . . ? C4 C5 C6 112.08(14) . . ? C7 C6 C10 107.04(15) . . ? C7 C6 C5 129.42(15) . . ? C10 C6 C5 123.53(16) . . ? C6 C7 N2 108.99(15) . . ? C6 C7 C8 131.32(16) . . ? N2 C7 C8 119.54(15) . . ? O1 C8 C7 120.37(17) . . ? O1 C8 C9 119.35(17) . . ? C7 C8 C9 120.20(16) . . ? C8 C9 C3 116.63(15) . . ? C11 C10 C15 119.24(17) . . ? C11 C10 C6 134.01(18) . . ? C15 C10 C6 106.75(15) . . ? C12 C11 C10 118.7(2) . . ? C11 C12 C13 121.0(2) . . ? C14 C13 C12 122.12(19) . . ? C13 C14 C15 117.0(2) . . ? N2 C15 C14 129.36(19) . . ? N2 C15 C10 108.70(15) . . ? C14 C15 C10 121.94(19) . . ? O2 C19 N3 120.39(17) . . ? O2 C19 C2 119.71(17) . . ? N3 C19 C2 119.81(16) . . ? N3 C20 C21 102.57(19) . . ? C22 C21 C20 103.2(2) . . ? C21 C22 C23 104.5(2) . . ? N3 C23 C24 109.30(17) . . ? N3 C23 C22 103.18(19) . . ? C24 C23 C22 115.2(2) . . ? O3 C24 C23 109.03(18) . . ?