# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name S.Caddick D.Pardoe N.R.Treweeke _publ_contact_author_name 'Prof S Caddick' _publ_contact_author_address ; Department of Chemistry University College London 20 Gordon Street London WC1H OAJ UNITED KINGDOM ; _publ_contact_author_email S.CADDICK@UCL.AC.UK _publ_section_title ; Controlling diastereoselectivity in the reactions of enantiomerically pure a-bromoacyl-imidazolidinones with nitrogen nucleophiles. Substitution reactions with retention or inversion of configuration. ; _publ_requested_category FO data_(4b)-dec400 _database_code_depnum_ccdc_archive 'CCDC 261877' _audit_creation_date 2000-12-13T09:33:03-00:00 _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 #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C21 H23 Br1 N2 O2' _chemical_formula_structural 'C21 H23 BR N2 O2' _chemical_formula_sum 'C21 H23 Br N2 O2' _chemical_formula_weight 415.32 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) _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 10.3839(12) _cell_length_b 6.2094(4) _cell_length_c 15.9554(18) _cell_angle_alpha 90 _cell_angle_beta 108.513(4) _cell_angle_gamma 90 _cell_volume 975.53(17) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7834 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.124 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.665 _exptl_absorpt_correction_T_max 0.741 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device KappaCCD _diffrn_measurement_method CCD _diffrn_reflns_number 6524 _diffrn_reflns_av_R_equivalents 0.0768 _diffrn_reflns_av_unetI/netI 0.096 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.88 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _reflns_number_total 3198 _reflns_number_gt 2534 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0206P)^2^+0.3960P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3198 _refine_ls_number_parameters 237 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0728 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.104 _refine_ls_wR_factor_gt 0.0951 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.013(14) _refine_diff_density_max 0.262 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.064 #----------------------------------------------------------------------------# # 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' Br Br -0.2901 2.4595 '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 Br Br 0.12239(5) 0.31669(10) 0.50704(4) 0.04764(19) Uani 1 1 d . . . O1 O 0.0897(4) 0.6255(6) 0.3267(3) 0.0509(11) Uani 1 1 d . . . O2 O 0.3873(4) 0.1423(5) 0.4166(3) 0.0362(9) Uani 1 1 d . . . N1 N 0.2962(4) 0.4752(6) 0.3555(3) 0.0314(11) Uani 1 1 d . . . N2 N 0.5139(5) 0.4021(6) 0.3780(3) 0.0347(11) Uani 1 1 d . . . C1 C 0.3997(4) 0.3195(11) 0.3876(3) 0.0308(10) Uani 1 1 d . . . C2 C 0.3466(5) 0.6689(8) 0.3226(4) 0.0307(12) Uani 1 1 d . . . H2 H 0.3245 0.7984 0.3527 0.037 Uiso 1 1 calc R . . C3 C 0.5048(5) 0.6323(8) 0.3567(4) 0.0350(13) Uani 1 1 d . . . H3 H 0.5453 0.7168 0.4123 0.042 Uiso 1 1 calc R . . C4 C 0.5780(5) 0.6884(10) 0.2912(4) 0.0465(15) Uani 1 1 d . . . H4A H 0.6753 0.66 0.3179 0.07 Uiso 1 1 calc R . . H4B H 0.564 0.8411 0.2755 0.07 Uiso 1 1 calc R . . H4C H 0.542 0.6002 0.2379 0.07 Uiso 1 1 calc R . . C5 C 0.6434(5) 0.2961(12) 0.4179(4) 0.0465(14) Uani 1 1 d . . . H5A H 0.6976 0.3795 0.4692 0.07 Uiso 1 1 calc R . . H5B H 0.6922 0.2861 0.3746 0.07 Uiso 1 1 calc R . . H5C H 0.628 0.1511 0.437 0.07 Uiso 1 1 calc R . . C6 C 0.2845(6) 0.6968(9) 0.2233(4) 0.0344(15) Uani 1 1 d . . . C7 C 0.2509(7) 0.8994(9) 0.1897(5) 0.0463(19) Uani 1 1 d . . . H7 H 0.267 1.0196 0.2285 0.056 Uiso 1 1 calc R . . C8 C 0.1934(7) 0.9306(11) 0.0991(5) 0.0565(19) Uani 1 1 d . . . H8 H 0.171 1.0723 0.0768 0.068 Uiso 1 1 calc R . . C9 C 0.1689(6) 0.7628(10) 0.0423(5) 0.053(2) Uani 1 1 d . . . H9 H 0.1287 0.7862 -0.0194 0.064 Uiso 1 1 calc R . . C10 C 0.2021(8) 0.5608(11) 0.0740(4) 0.065(2) Uani 1 1 d . . . H10 H 0.1866 0.4424 0.0343 0.078 Uiso 1 1 calc R . . C11 C 0.2591(8) 0.5259(9) 0.1649(5) 0.062(2) Uani 1 1 d . . . H11 H 0.2806 0.3836 0.1867 0.075 Uiso 1 1 calc R . . C12 C 0.1617(6) 0.4702(9) 0.3525(4) 0.0429(15) Uani 1 1 d . . . C13 C 0.1087(5) 0.2673(8) 0.3841(4) 0.0370(15) Uani 1 1 d . . . H13 H 0.1677 0.1426 0.3806 0.044 Uiso 1 1 calc R . . C14 C -0.0373(5) 0.2183(9) 0.3292(4) 0.0392(14) Uani 1 1 d . . . H14A H -0.0731 0.1012 0.3577 0.047 Uiso 1 1 calc R . . H14B H -0.0941 0.3477 0.3266 0.047 Uiso 1 1 calc R . . C15 C -0.0459(5) 0.1510(10) 0.2362(4) 0.0472(16) Uani 1 1 d . . . H15A H -0.0217 0.2757 0.2055 0.057 Uiso 1 1 calc R . . H15B H 0.0218 0.0362 0.2397 0.057 Uiso 1 1 calc R . . C16 C -0.1847(6) 0.0699(9) 0.1820(4) 0.0411(15) Uani 1 1 d . . . C17 C -0.2997(6) 0.1971(10) 0.1680(4) 0.0442(15) Uani 1 1 d . . . H17 H -0.2909 0.3381 0.1923 0.053 Uiso 1 1 calc R . . C18 C -0.4274(6) 0.1214(11) 0.1192(4) 0.0545(18) Uani 1 1 d . . . H18 H -0.5047 0.2115 0.1097 0.065 Uiso 1 1 calc R . . C19 C -0.4424(7) -0.0819(11) 0.0847(4) 0.0545(18) Uani 1 1 d . . . H19 H -0.5299 -0.1339 0.0518 0.065 Uiso 1 1 calc R . . C20 C -0.3296(7) -0.2114(13) 0.0981(4) 0.0544(17) Uani 1 1 d . . . H20 H -0.3392 -0.3517 0.0731 0.065 Uiso 1 1 calc R . . C21 C -0.2013(6) -0.1371(9) 0.1482(4) 0.0503(18) Uani 1 1 d . . . H21 H -0.1248 -0.2295 0.1592 0.06 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 Br 0.0442(3) 0.0545(3) 0.0422(3) -0.0032(4) 0.0107(2) -0.0036(4) O1 0.041(2) 0.045(2) 0.070(3) 0.015(2) 0.024(2) 0.015(2) O2 0.035(2) 0.0255(19) 0.047(3) -0.0007(18) 0.0118(19) 0.0013(16) N1 0.027(3) 0.029(2) 0.039(3) 0.000(2) 0.012(2) 0.0028(19) N2 0.028(3) 0.034(2) 0.044(3) 0.0042(19) 0.014(2) 0.0021(17) C1 0.033(3) 0.026(3) 0.031(3) -0.010(4) 0.007(2) 0.002(3) C2 0.037(3) 0.024(3) 0.033(3) 0.003(2) 0.015(3) 0.002(2) C3 0.039(3) 0.033(3) 0.034(3) -0.003(2) 0.011(3) -0.007(2) C4 0.035(3) 0.055(3) 0.049(4) 0.009(3) 0.012(3) -0.008(3) C5 0.035(3) 0.049(3) 0.056(4) 0.009(4) 0.015(3) 0.003(3) C6 0.037(3) 0.030(3) 0.038(4) -0.005(3) 0.015(3) -0.003(2) C7 0.055(4) 0.033(3) 0.046(5) 0.001(3) 0.009(3) 0.007(3) C8 0.067(5) 0.050(4) 0.048(5) 0.017(4) 0.012(4) 0.016(3) C9 0.053(4) 0.063(6) 0.039(4) 0.005(3) 0.006(3) -0.005(3) C10 0.102(6) 0.052(4) 0.029(4) -0.011(3) 0.002(4) -0.017(4) C11 0.098(6) 0.031(3) 0.044(5) -0.002(3) 0.003(4) 0.001(3) C12 0.045(4) 0.035(3) 0.050(4) -0.002(3) 0.018(3) 0.002(3) C13 0.033(3) 0.036(4) 0.040(3) -0.001(2) 0.009(3) -0.002(2) C14 0.032(3) 0.049(3) 0.034(4) 0.001(3) 0.007(3) -0.005(2) C15 0.029(3) 0.066(4) 0.047(4) -0.005(3) 0.012(3) -0.001(3) C16 0.035(3) 0.050(4) 0.033(4) 0.007(3) 0.004(3) 0.004(3) C17 0.045(4) 0.044(3) 0.041(4) 0.009(3) 0.011(3) 0.004(3) C18 0.040(4) 0.075(5) 0.042(4) 0.016(4) 0.004(3) 0.004(3) C19 0.041(4) 0.071(4) 0.044(4) 0.013(3) 0.004(3) -0.012(3) C20 0.073(4) 0.046(4) 0.039(3) -0.005(3) 0.011(3) -0.013(4) C21 0.055(4) 0.050(5) 0.040(4) 0.005(3) 0.008(3) 0.005(3) #----------------------------------------------------------------------------# # 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 Br C13 1.945(6) . ? O1 C12 1.209(6) . ? O2 C1 1.217(7) . ? N1 C12 1.383(7) . ? N1 C1 1.416(7) . ? N1 C2 1.473(6) . ? N2 C1 1.344(6) . ? N2 C5 1.451(7) . ? N2 C3 1.465(6) . ? C2 C6 1.518(8) . ? C2 C3 1.575(7) . ? C3 C4 1.515(8) . ? C6 C7 1.369(7) . ? C6 C11 1.381(8) . ? C7 C8 1.391(9) . ? C8 C9 1.351(8) . ? C9 C10 1.355(9) . ? C10 C11 1.399(9) . ? C12 C13 1.524(7) . ? C13 C14 1.521(7) . ? C14 C15 1.517(8) . ? C15 C16 1.512(8) . ? C16 C21 1.383(8) . ? C16 C17 1.390(8) . ? C17 C18 1.390(8) . ? C18 C19 1.366(9) . ? C19 C20 1.381(9) . ? C20 C21 1.396(8) . ? 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 C12 N1 C1 129.8(5) . . ? C12 N1 C2 118.4(4) . . ? C1 N1 C2 111.8(4) . . ? C1 N2 C5 120.3(5) . . ? C1 N2 C3 113.9(5) . . ? C5 N2 C3 121.8(5) . . ? O2 C1 N2 126.4(5) . . ? O2 C1 N1 126.5(4) . . ? N2 C1 N1 107.1(5) . . ? N1 C2 C6 112.5(4) . . ? N1 C2 C3 102.0(4) . . ? C6 C2 C3 115.4(5) . . ? N2 C3 C4 112.0(5) . . ? N2 C3 C2 101.8(4) . . ? C4 C3 C2 115.1(5) . . ? C7 C6 C11 118.1(6) . . ? C7 C6 C2 119.0(5) . . ? C11 C6 C2 122.9(5) . . ? C6 C7 C8 120.5(6) . . ? C9 C8 C7 121.1(6) . . ? C8 C9 C10 119.5(7) . . ? C9 C10 C11 120.2(7) . . ? C6 C11 C10 120.5(6) . . ? O1 C12 N1 120.1(5) . . ? O1 C12 C13 121.5(5) . . ? N1 C12 C13 118.3(5) . . ? C14 C13 C12 111.9(5) . . ? C14 C13 Br 110.7(4) . . ? C12 C13 Br 106.5(4) . . ? C15 C14 C13 110.9(5) . . ? C16 C15 C14 113.6(5) . . ? C21 C16 C17 118.1(5) . . ? C21 C16 C15 120.7(5) . . ? C17 C16 C15 121.1(5) . . ? C16 C17 C18 121.1(6) . . ? C19 C18 C17 120.3(6) . . ? C18 C19 C20 119.6(6) . . ? C19 C20 C21 120.3(7) . . ? C16 C21 C20 120.6(6) . . ? #======END data_(5b)-dec1400 _database_code_depnum_ccdc_archive 'CCDC 261878' _audit_creation_date 2000-12-20T16:25:19-00:00 _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 #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C27 H39 N3 O2' _chemical_formula_structural 'C27 H39 N3 O2' _chemical_formula_sum 'C28 H31 N3 O2' _chemical_formula_weight 441.56 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.5902(3) _cell_length_b 10.3216(4) _cell_length_c 24.9928(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2473.94(16) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9431 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.186 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION NOT APPLIED # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_max 0.9925 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device KappaCCD _diffrn_measurement_method CCD _diffrn_reflns_number 12753 _diffrn_reflns_av_R_equivalents 0.0589 _diffrn_reflns_av_unetI/netI 0.0637 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.79 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _reflns_number_total 4334 _reflns_number_gt 3264 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0584P)^2^+0.0288P] 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 SHELXL _refine_ls_extinction_expression Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.031(3) _refine_ls_number_reflns 4334 _refine_ls_number_parameters 305 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0715 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1115 _refine_ls_wR_factor_gt 0.1005 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(15) _refine_diff_density_max 0.113 _refine_diff_density_min -0.134 _refine_diff_density_rms 0.03 #----------------------------------------------------------------------------# # 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 0.19852(17) 0.00811(15) 0.18353(6) 0.0520(4) Uani 1 1 d . . . O2 O -0.05796(16) 0.32076(16) 0.14677(7) 0.0548(4) Uani 1 1 d . . . N1 N 0.2649(2) 0.14486(19) 0.25139(7) 0.0487(5) Uani 1 1 d . . . N2 N 0.11041(19) 0.21868(17) 0.19284(7) 0.0418(4) Uani 1 1 d . . . N3 N 0.0063(2) 0.1920(2) 0.05073(7) 0.0510(5) Uani 1 1 d . . . H3A H -0.084(3) 0.219(2) 0.0492(9) 0.045(6) Uiso 1 1 d . . . C1 C 0.1938(2) 0.1119(2) 0.20690(9) 0.0429(6) Uani 1 1 d . . . C2 C 0.2155(2) 0.2645(2) 0.27587(9) 0.0490(6) Uani 1 1 d . . . H2 H 0.1514 0.2418 0.306 0.059 Uiso 1 1 calc R . . C3 C 0.1277(2) 0.3270(2) 0.22997(9) 0.0427(5) Uani 1 1 d . . . H3 H 0.0341 0.3511 0.2445 0.051 Uiso 1 1 calc R . . C4 C 0.3396(3) 0.0461(3) 0.28128(10) 0.0711(8) Uani 1 1 d . . . H4C H 0.3589 -0.0279 0.2579 0.107 Uiso 1 1 calc R . . H4B H 0.2826 0.0176 0.3116 0.107 Uiso 1 1 calc R . . H4A H 0.4277 0.082 0.2945 0.107 Uiso 1 1 calc R . . C5 C 0.3333(3) 0.3460(3) 0.29767(12) 0.0708(8) Uani 1 1 d . . . H5C H 0.4034 0.3593 0.2697 0.106 Uiso 1 1 calc R . . H5B H 0.3761 0.3016 0.3282 0.106 Uiso 1 1 calc R . . H5A H 0.2967 0.4301 0.3093 0.106 Uiso 1 1 calc R . . C6 C 0.1907(2) 0.4446(2) 0.20331(9) 0.0418(5) Uani 1 1 d . . . C7 C 0.1603(3) 0.5671(3) 0.22219(13) 0.0629(7) Uani 1 1 d . . . H7 H 0.1002 0.576 0.2522 0.076 Uiso 1 1 calc R . . C8 C 0.2143(3) 0.6761(3) 0.19889(17) 0.0834(10) Uani 1 1 d . . . H8 H 0.1921 0.7592 0.2128 0.1 Uiso 1 1 calc R . . C9 C 0.3007(3) 0.6649(3) 0.15520(17) 0.0865(11) Uani 1 1 d . . . H9 H 0.3383 0.7401 0.1388 0.104 Uiso 1 1 calc R . . C10 C 0.3322(3) 0.5448(3) 0.13556(13) 0.0745(9) Uani 1 1 d . . . H10 H 0.391 0.537 0.1052 0.089 Uiso 1 1 calc R . . C11 C 0.2787(2) 0.4338(3) 0.15978(10) 0.0535(6) Uani 1 1 d . . . H11 H 0.3027 0.3507 0.1463 0.064 Uiso 1 1 calc R . . C12 C 0.0244(2) 0.2307(2) 0.14848(9) 0.0427(5) Uani 1 1 d . . . C13 C 0.0401(2) 0.1347(2) 0.10248(9) 0.0450(6) Uani 1 1 d . . . H13 H 0.1394 0.1052 0.1014 0.054 Uiso 1 1 calc R . . C14 C -0.0525(2) 0.0156(2) 0.11082(9) 0.0462(6) Uani 1 1 d . . . H14B H -0.0443 -0.0144 0.1483 0.055 Uiso 1 1 calc R . . H14A H -0.1511 0.0393 0.1043 0.055 Uiso 1 1 calc R . . C15 C -0.0102(3) -0.0931(2) 0.07311(10) 0.0597(7) Uani 1 1 d . . . H15B H 0.0057 -0.0562 0.0371 0.072 Uiso 1 1 calc R . . H15A H 0.0791 -0.1303 0.0856 0.072 Uiso 1 1 calc R . . C16 C -0.1167(2) -0.2004(2) 0.06883(9) 0.0456(6) Uani 1 1 d . . . C17 C -0.2468(3) -0.1750(3) 0.04623(10) 0.0609(7) Uani 1 1 d . . . H17 H -0.2668 -0.0904 0.0334 0.073 Uiso 1 1 calc R . . C18 C -0.3468(3) -0.2702(3) 0.04224(12) 0.0692(8) Uani 1 1 d . . . H18 H -0.4355 -0.2511 0.0273 0.083 Uiso 1 1 calc R . . C19 C -0.3171(3) -0.3930(3) 0.06000(11) 0.0609(7) Uani 1 1 d . . . H19 H -0.3849 -0.4596 0.0566 0.073 Uiso 1 1 calc R . . C20 C -0.1897(3) -0.4204(2) 0.08267(10) 0.0503(6) Uani 1 1 d . . . H20 H -0.1699 -0.5052 0.0953 0.06 Uiso 1 1 calc R . . C21 C -0.0910(2) -0.3237(2) 0.08700(9) 0.0462(6) Uani 1 1 d . . . H21 H -0.0034 -0.3428 0.1029 0.055 Uiso 1 1 calc R . . C22 C 0.0994(3) 0.2969(3) 0.03337(10) 0.0583(7) Uani 1 1 d . . . H22B H 0.1979 0.2698 0.0375 0.07 Uiso 1 1 calc R . . H22A H 0.0839 0.3748 0.0557 0.07 Uiso 1 1 calc R . . C23 C 0.0695(2) 0.3277(2) -0.02454(9) 0.0452(6) Uani 1 1 d . . . C24 C 0.1268(3) 0.2553(3) -0.06529(11) 0.0577(7) Uani 1 1 d . . . H24 H 0.1885 0.1864 -0.0566 0.069 Uiso 1 1 calc R . . C25 C 0.0974(3) 0.2799(3) -0.11787(11) 0.0697(8) Uani 1 1 d . . . H25 H 0.139 0.2289 -0.1452 0.084 Uiso 1 1 calc R . . C26 C 0.0078(3) 0.3781(3) -0.13101(10) 0.0658(8) Uani 1 1 d . . . H26 H -0.0138 0.3946 -0.1675 0.079 Uiso 1 1 calc R . . C27 C -0.0508(3) 0.4527(3) -0.09173(11) 0.0632(7) Uani 1 1 d . . . H27 H -0.1123 0.5214 -0.1009 0.076 Uiso 1 1 calc R . . C28 C -0.0202(2) 0.4278(3) -0.03825(10) 0.0535(6) Uani 1 1 d . . . H28 H -0.061 0.4796 -0.011 0.064 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 0.0690(10) 0.0332(9) 0.0536(9) 0.0034(8) -0.0029(8) 0.0028(8) O2 0.0514(9) 0.0437(10) 0.0692(11) -0.0036(9) -0.0125(8) 0.0005(8) N1 0.0580(11) 0.0458(13) 0.0423(11) 0.0015(9) -0.0048(9) 0.0074(10) N2 0.0481(10) 0.0310(10) 0.0461(10) 0.0021(9) -0.0054(9) -0.0013(8) N3 0.0511(12) 0.0506(13) 0.0514(12) 0.0097(10) -0.0084(10) -0.0111(10) C1 0.0476(12) 0.0343(13) 0.0468(13) 0.0050(11) 0.0046(11) -0.0029(11) C2 0.0565(13) 0.0474(14) 0.0431(12) -0.0010(11) 0.0022(11) 0.0008(12) C3 0.0434(11) 0.0367(13) 0.0481(12) -0.0066(11) 0.0033(10) -0.0020(10) C4 0.092(2) 0.0685(19) 0.0527(15) 0.0026(14) -0.0178(14) 0.0220(17) C5 0.0744(17) 0.0652(19) 0.0727(18) -0.0077(16) -0.0269(15) -0.0039(15) C6 0.0385(11) 0.0333(12) 0.0537(14) -0.0014(11) -0.0041(11) 0.0004(10) C7 0.0572(15) 0.0397(15) 0.092(2) -0.0075(15) -0.0022(14) 0.0040(13) C8 0.0691(19) 0.0358(16) 0.145(3) 0.0004(19) -0.021(2) -0.0027(15) C9 0.0625(17) 0.053(2) 0.144(3) 0.041(2) -0.028(2) -0.0200(16) C10 0.0596(16) 0.080(2) 0.084(2) 0.0265(18) -0.0011(15) -0.0204(16) C11 0.0485(13) 0.0487(15) 0.0633(15) 0.0040(13) -0.0004(12) -0.0037(12) C12 0.0451(11) 0.0287(12) 0.0544(14) 0.0029(11) -0.0005(11) -0.0046(11) C13 0.0476(12) 0.0399(14) 0.0476(13) 0.0051(11) -0.0044(10) -0.0071(11) C14 0.0537(12) 0.0387(13) 0.0461(12) -0.0010(11) 0.0014(11) -0.0065(11) C15 0.0638(15) 0.0435(15) 0.0718(17) -0.0123(13) 0.0107(14) -0.0066(13) C16 0.0538(13) 0.0389(14) 0.0441(12) -0.0094(11) 0.0028(11) 0.0013(11) C17 0.0784(17) 0.0413(15) 0.0630(15) -0.0078(13) -0.0218(14) 0.0077(14) C18 0.0682(17) 0.0533(18) 0.086(2) -0.0224(15) -0.0285(15) 0.0122(15) C19 0.0572(15) 0.0455(16) 0.0800(18) -0.0163(14) -0.0025(14) -0.0054(13) C20 0.0652(15) 0.0357(14) 0.0502(14) -0.0008(11) 0.0034(12) 0.0009(12) C21 0.0512(13) 0.0430(15) 0.0444(12) -0.0078(11) -0.0029(11) 0.0066(12) C22 0.0634(15) 0.0560(16) 0.0554(14) 0.0159(13) -0.0081(12) -0.0189(13) C23 0.0462(12) 0.0387(14) 0.0508(13) 0.0053(12) -0.0017(11) -0.0071(11) C24 0.0533(14) 0.0470(16) 0.0729(18) -0.0058(14) -0.0056(13) 0.0004(13) C25 0.0661(16) 0.080(2) 0.0627(18) -0.0185(16) 0.0059(15) -0.0158(17) C26 0.0705(17) 0.080(2) 0.0474(15) 0.0063(15) -0.0060(14) -0.0265(17) C27 0.0621(15) 0.0489(16) 0.0785(19) 0.0234(15) -0.0160(15) -0.0058(14) C28 0.0552(14) 0.0454(15) 0.0599(15) -0.0018(12) 0.0035(12) -0.0015(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 O1 C1 1.221(3) . ? O2 C12 1.221(3) . ? N1 C1 1.348(3) . ? N1 C4 1.453(3) . ? N1 C2 1.457(3) . ? N2 C12 1.387(3) . ? N2 C1 1.406(3) . ? N2 C3 1.463(3) . ? N3 C13 1.459(3) . ? N3 C22 1.469(3) . ? C2 C5 1.510(3) . ? C2 C3 1.562(3) . ? C3 C6 1.511(3) . ? C6 C11 1.381(3) . ? C6 C7 1.381(3) . ? C7 C8 1.368(4) . ? C8 C9 1.376(5) . ? C9 C10 1.366(5) . ? C10 C11 1.393(4) . ? C12 C13 1.525(3) . ? C13 C14 1.531(3) . ? C14 C15 1.520(3) . ? C15 C16 1.510(3) . ? C16 C21 1.373(3) . ? C16 C17 1.395(4) . ? C17 C18 1.377(4) . ? C18 C19 1.373(4) . ? C19 C20 1.376(4) . ? C20 C21 1.380(3) . ? C22 C23 1.509(3) . ? C23 C24 1.378(4) . ? C23 C28 1.387(3) . ? C24 C25 1.368(4) . ? C25 C26 1.369(4) . ? C26 C27 1.368(4) . ? C27 C28 1.392(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 119.8(2) . . ? C1 N1 C2 113.29(18) . . ? C4 N1 C2 122.6(2) . . ? C12 N2 C1 127.43(19) . . ? C12 N2 C3 120.43(18) . . ? C1 N2 C3 112.07(17) . . ? C13 N3 C22 115.18(18) . . ? O1 C1 N1 126.7(2) . . ? O1 C1 N2 126.1(2) . . ? N1 C1 N2 107.2(2) . . ? N1 C2 C5 112.4(2) . . ? N1 C2 C3 102.53(18) . . ? C5 C2 C3 115.9(2) . . ? N2 C3 C6 112.31(18) . . ? N2 C3 C2 102.20(17) . . ? C6 C3 C2 116.12(18) . . ? C11 C6 C7 118.1(2) . . ? C11 C6 C3 121.8(2) . . ? C7 C6 C3 120.0(2) . . ? C8 C7 C6 121.9(3) . . ? C7 C8 C9 119.7(3) . . ? C10 C9 C8 119.7(3) . . ? C9 C10 C11 120.5(3) . . ? C6 C11 C10 120.1(3) . . ? O2 C12 N2 118.7(2) . . ? O2 C12 C13 122.2(2) . . ? N2 C12 C13 119.06(19) . . ? N3 C13 C12 112.52(19) . . ? N3 C13 C14 108.49(18) . . ? C12 C13 C14 111.18(18) . . ? C15 C14 C13 110.67(19) . . ? C16 C15 C14 113.89(19) . . ? C21 C16 C17 118.0(2) . . ? C21 C16 C15 122.3(2) . . ? C17 C16 C15 119.7(2) . . ? C18 C17 C16 121.2(2) . . ? C19 C18 C17 119.4(2) . . ? C18 C19 C20 120.4(3) . . ? C19 C20 C21 119.6(2) . . ? C16 C21 C20 121.4(2) . . ? N3 C22 C23 108.83(19) . . ? C24 C23 C28 118.0(2) . . ? C24 C23 C22 121.2(2) . . ? C28 C23 C22 120.8(2) . . ? C25 C24 C23 121.8(3) . . ? C24 C25 C26 119.8(3) . . ? C27 C26 C25 120.2(2) . . ? C26 C27 C28 119.9(3) . . ? C23 C28 C27 120.4(2) . . ? #======END data_(6b)-may2601 _database_code_depnum_ccdc_archive 'CCDC 261879' _audit_creation_date 2001-05-23T09:50:33-00:00 _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 #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C21 H23 N5 O2' _chemical_formula_structural 'C21 H23 N5 O2' _chemical_formula_sum 'C21 H23 N5 O2' _chemical_formula_weight 377.44 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2 _symmetry_space_group_name_Hall 'C 2y' _symmetry_Int_Tables_number 5 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 19.2790(16) _cell_length_b 6.0518(8) _cell_length_c 17.189(2) _cell_angle_alpha 90 _cell_angle_beta 99.200(8) _cell_angle_gamma 90 _cell_volume 1979.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4974 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 22.986 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device KappaCCD _diffrn_measurement_method CCD _diffrn_reflns_number 4206 _diffrn_reflns_av_R_equivalents 0.0869 _diffrn_reflns_av_unetI/netI 0.0975 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.79 _diffrn_reflns_theta_max 23.01 _diffrn_reflns_theta_full 23.01 _diffrn_measured_fraction_theta_full 0.979 _diffrn_measured_fraction_theta_max 0.979 _reflns_number_total 2477 _reflns_number_gt 2118 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.1713P)^2^+1.9828P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^==kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.017(6) _refine_ls_number_reflns 2477 _refine_ls_number_parameters 256 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0981 _refine_ls_R_factor_gt 0.0861 _refine_ls_wR_factor_ref 0.2454 _refine_ls_wR_factor_gt 0.2292 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -8(4) _refine_diff_density_max 0.286 _refine_diff_density_min -0.395 _refine_diff_density_rms 0.081 #----------------------------------------------------------------------------# # 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 0.2754(2) -0.0034(8) 0.0816(2) 0.0380(11) Uani 1 1 d . . . O2 O 0.2256(3) -0.4769(8) 0.2442(3) 0.0515(13) Uani 1 1 d . . . N1 N 0.3486(3) -0.2879(9) 0.0593(3) 0.0350(13) Uani 1 1 d . . . N2 N 0.2842(2) -0.3366(8) 0.1535(2) 0.0302(11) Uani 1 1 d . . . N3 N 0.1201(3) -0.2053(11) 0.1299(3) 0.0452(15) Uani 1 1 d . . . N4 N 0.0872(3) -0.3627(12) 0.1514(3) 0.0477(15) Uani 1 1 d . . . N5 N 0.0532(4) -0.5095(15) 0.1628(4) 0.071(2) Uani 1 1 d . . . C1 C 0.3009(3) -0.1877(11) 0.0951(3) 0.0314(15) Uani 1 1 d . . . C2 C 0.3580(3) -0.5227(11) 0.0773(3) 0.0349(14) Uani 1 1 d . . . H2 H 0.3253 -0.6076 0.0372 0.042 Uiso 1 1 calc R . . C3 C 0.3290(3) -0.5340(10) 0.1580(3) 0.0321(14) Uani 1 1 d . . . H3 H 0.2991 -0.6689 0.1585 0.039 Uiso 1 1 calc R . . C4 C 0.3703(4) -0.1920(13) -0.0120(4) 0.054(2) Uani 1 1 d . . . H4A H 0.3441 -0.263 -0.0589 0.08 Uiso 1 1 calc R . . H4B H 0.4208 -0.2162 -0.0106 0.08 Uiso 1 1 calc R . . H4C H 0.3605 -0.033 -0.0138 0.08 Uiso 1 1 calc R . . C5 C 0.4301(4) -0.6093(15) 0.0780(4) 0.054(2) Uani 1 1 d . . . H5A H 0.4409 -0.6095 0.0242 0.082 Uiso 1 1 calc R . . H5B H 0.4331 -0.7604 0.0988 0.082 Uiso 1 1 calc R . . H5C H 0.4639 -0.5152 0.1115 0.082 Uiso 1 1 calc R . . C6 C 0.3859(3) -0.5360(11) 0.2295(3) 0.0335(14) Uani 1 1 d . . . C7 C 0.3983(3) -0.7243(12) 0.2756(3) 0.0437(16) Uani 1 1 d . . . H7 H 0.3696 -0.851 0.2632 0.052 Uiso 1 1 calc R . . C8 C 0.4519(4) -0.7298(15) 0.3393(4) 0.055(2) Uani 1 1 d . . . H8 H 0.46 -0.8609 0.3698 0.066 Uiso 1 1 calc R . . C9 C 0.4941(4) -0.5455(15) 0.3592(4) 0.055(2) Uani 1 1 d . . . H9 H 0.5302 -0.5484 0.4037 0.066 Uiso 1 1 calc R . . C10 C 0.4826(3) -0.3610(13) 0.3138(4) 0.0478(17) Uani 1 1 d . . . H10 H 0.5121 -0.2356 0.3259 0.057 Uiso 1 1 calc R . . C11 C 0.4287(4) -0.3535(13) 0.2502(3) 0.0451(16) Uani 1 1 d . . . H11 H 0.4207 -0.2215 0.2202 0.054 Uiso 1 1 calc R . . C12 C 0.2327(3) -0.3244(11) 0.2000(3) 0.0351(14) Uani 1 1 d . . . C13 C 0.1806(3) -0.1319(11) 0.1899(3) 0.0358(15) Uani 1 1 d . . . H13 H 0.2034 -0.0013 0.1689 0.043 Uiso 1 1 calc R . . C14 C 0.1563(3) -0.0669(11) 0.2677(3) 0.0365(15) Uani 1 1 d . . . H14A H 0.1357 -0.1978 0.2899 0.044 Uiso 1 1 calc R . . H14B H 0.1192 0.047 0.2569 0.044 Uiso 1 1 calc R . . C15 C 0.2169(3) 0.0235(12) 0.3289(3) 0.0392(16) Uani 1 1 d . . . H15A H 0.2517 -0.0949 0.345 0.047 Uiso 1 1 calc R . . H15B H 0.2409 0.1455 0.3055 0.047 Uiso 1 1 calc R . . C16 C 0.1873(3) 0.1074(11) 0.4006(3) 0.0319(14) Uani 1 1 d . . . C17 C 0.1575(3) 0.3107(12) 0.4017(3) 0.0418(16) Uani 1 1 d . . . H17 H 0.1575 0.4069 0.358 0.05 Uiso 1 1 calc R . . C18 C 0.1269(4) 0.3807(13) 0.4659(4) 0.0481(18) Uani 1 1 d . . . H18 H 0.1047 0.521 0.4652 0.058 Uiso 1 1 calc R . . C19 C 0.1294(4) 0.2414(14) 0.5309(4) 0.055(2) Uani 1 1 d . . . H19 H 0.1096 0.2882 0.5753 0.066 Uiso 1 1 calc R . . C20 C 0.1598(4) 0.0410(14) 0.5311(4) 0.051(2) Uani 1 1 d . . . H20 H 0.1611 -0.0519 0.5759 0.061 Uiso 1 1 calc R . . C21 C 0.1896(3) -0.0334(12) 0.4663(3) 0.0414(16) Uani 1 1 d . . . H21 H 0.2107 -0.1752 0.4668 0.05 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 0.055(3) 0.033(3) 0.029(2) 0.0038(19) 0.0146(18) 0.002(2) O2 0.068(3) 0.049(3) 0.046(3) 0.017(2) 0.035(2) 0.015(2) N1 0.045(3) 0.041(3) 0.022(2) 0.001(2) 0.015(2) -0.002(2) N2 0.038(3) 0.032(3) 0.022(2) 0.000(2) 0.0110(18) 0.000(2) N3 0.055(3) 0.057(4) 0.024(2) 0.000(3) 0.009(2) 0.011(3) N4 0.052(3) 0.063(5) 0.028(3) -0.004(3) 0.008(2) 0.006(4) N5 0.073(5) 0.084(6) 0.058(4) -0.016(4) 0.017(3) -0.011(5) C1 0.037(3) 0.040(4) 0.017(3) 0.000(3) 0.004(2) -0.007(3) C2 0.042(3) 0.042(4) 0.023(3) -0.007(3) 0.009(2) 0.000(3) C3 0.043(3) 0.031(4) 0.025(3) -0.004(3) 0.014(2) -0.002(3) C4 0.081(5) 0.056(5) 0.033(3) 0.004(3) 0.036(3) -0.014(4) C5 0.058(4) 0.077(5) 0.033(3) -0.002(3) 0.020(3) 0.007(4) C6 0.040(3) 0.039(4) 0.024(3) -0.002(3) 0.012(2) 0.005(3) C7 0.049(4) 0.051(4) 0.033(3) 0.006(3) 0.015(3) 0.011(3) C8 0.067(4) 0.063(5) 0.039(4) 0.018(4) 0.018(3) 0.021(4) C9 0.061(4) 0.080(6) 0.025(3) -0.006(4) 0.009(3) 0.017(4) C10 0.052(4) 0.057(5) 0.035(3) -0.012(4) 0.007(3) 0.004(4) C11 0.060(4) 0.048(4) 0.029(3) -0.005(3) 0.012(3) 0.002(3) C12 0.044(3) 0.039(4) 0.025(3) 0.005(3) 0.012(2) 0.005(3) C13 0.049(4) 0.043(4) 0.018(3) 0.002(3) 0.013(2) 0.011(3) C14 0.044(3) 0.044(4) 0.025(3) 0.000(3) 0.013(2) 0.005(3) C15 0.045(4) 0.049(4) 0.026(3) 0.000(3) 0.013(3) 0.008(3) C16 0.033(3) 0.036(4) 0.026(3) -0.003(3) 0.006(2) -0.003(3) C17 0.045(3) 0.054(5) 0.028(3) 0.000(3) 0.011(3) 0.000(3) C18 0.056(4) 0.051(4) 0.042(4) -0.009(3) 0.021(3) 0.001(3) C19 0.070(5) 0.067(5) 0.032(4) -0.013(3) 0.019(3) -0.006(4) C20 0.055(4) 0.074(6) 0.026(3) 0.014(3) 0.011(3) -0.005(4) C21 0.055(4) 0.043(4) 0.027(3) 0.003(3) 0.009(3) -0.008(3) #----------------------------------------------------------------------------# # 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 C1 1.225(8) . ? O2 C12 1.218(8) . ? N1 C1 1.332(8) . ? N1 C2 1.459(9) . ? N1 C4 1.476(7) . ? N2 C12 1.372(7) . ? N2 C1 1.424(7) . ? N2 C3 1.469(8) . ? N3 N4 1.234(9) . ? N3 C13 1.495(8) . ? N4 N5 1.139(10) . ? C2 C5 1.484(9) . ? C2 C3 1.577(7) . ? C3 C6 1.513(8) . ? C6 C7 1.386(9) . ? C6 C11 1.389(9) . ? C7 C8 1.380(9) . ? C8 C9 1.391(12) . ? C9 C10 1.359(11) . ? C10 C11 1.384(9) . ? C12 C13 1.530(9) . ? C13 C14 1.537(7) . ? C14 C15 1.541(9) . ? C15 C16 1.526(8) . ? C16 C17 1.359(9) . ? C16 C21 1.409(9) . ? C17 C18 1.398(9) . ? C18 C19 1.395(10) . ? C19 C20 1.346(11) . ? C20 C21 1.407(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 114.6(5) . . ? C1 N1 C4 120.9(6) . . ? C2 N1 C4 121.2(5) . . ? C12 N2 C1 130.0(5) . . ? C12 N2 C3 119.2(4) . . ? C1 N2 C3 110.7(4) . . ? N4 N3 C13 113.9(5) . . ? N5 N4 N3 172.5(6) . . ? O1 C1 N1 127.8(5) . . ? O1 C1 N2 125.4(5) . . ? N1 C1 N2 106.8(5) . . ? N1 C2 C5 115.5(6) . . ? N1 C2 C3 100.3(5) . . ? C5 C2 C3 116.2(5) . . ? N2 C3 C6 113.2(5) . . ? N2 C3 C2 102.0(4) . . ? C6 C3 C2 113.7(4) . . ? C7 C6 C11 117.8(6) . . ? C7 C6 C3 120.5(6) . . ? C11 C6 C3 121.7(6) . . ? C8 C7 C6 120.8(7) . . ? C7 C8 C9 120.6(7) . . ? C10 C9 C8 118.9(7) . . ? C9 C10 C11 120.8(7) . . ? C10 C11 C6 121.1(7) . . ? O2 C12 N2 119.2(5) . . ? O2 C12 C13 120.6(5) . . ? N2 C12 C13 119.9(5) . . ? N3 C13 C12 106.1(5) . . ? N3 C13 C14 111.4(5) . . ? C12 C13 C14 112.5(5) . . ? C13 C14 C15 112.5(5) . . ? C16 C15 C14 109.2(5) . . ? C17 C16 C21 119.7(6) . . ? C17 C16 C15 121.7(5) . . ? C21 C16 C15 118.5(6) . . ? C16 C17 C18 121.2(6) . . ? C19 C18 C17 119.0(7) . . ? C20 C19 C18 120.4(6) . . ? C19 C20 C21 121.2(6) . . ? C20 C21 C16 118.4(7) . . ? #======END