# Supplementary Material (ESI) for Chemical Science # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1475 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Mascarenas, Jose' 'Faustino, Helio' 'Lopez, Fernando' 'Castedo, Luis' _publ_contact_author_name ' Mascarenas, Jose' _publ_contact_author_email joseluis.mascarenas@usc.es _publ_section_title ; Gold(I)-catalyzed intermolecular (4+2) cycloaddition of allenamides and acyclic dienes ; # Attachment '- ccdc_deposit 3db.cif' data_lm04hff1n _database_code_depnum_ccdc_archive 'CCDC 804843' #TrackingRef '- ccdc_deposit 3db.cif' _audit_creation_date 2010-06-15T18:55:42-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common HF111A9B9 _chemical_formula_moiety 'C12 H17 N O2' _chemical_formula_sum 'C12 H17 N O2' _chemical_formula_weight 207.27 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 12.4376(4) _cell_length_b 6.2473(2) _cell_length_c 14.2135(5) _cell_angle_alpha 90 _cell_angle_beta 93.459(2) _cell_angle_gamma 90 _cell_volume 1102.40(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2154 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 26.45 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.28 _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8958 _exptl_absorpt_correction_T_max 0.9717 _exptl_absorpt_process_details 'BRUKER AXS - SADABS' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Bruker X8 kappa APEXII CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_unetI/netI 0.0377 _diffrn_reflns_number 10715 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.1 _diffrn_reflns_theta_full 27.1 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 2415 _reflns_number_gt 1906 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEXII v2010.3-0 (Bruker AXS, 2010)' _computing_cell_refinement 'APEXII v2010.3-0 (Bruker AXS, 2010)' _computing_data_reduction 'APEXII v2010.3-0 (Bruker AXS, 2010)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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^)+(0.0281P)^2^+0.6938P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refall _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 0.0163(15) _refine_ls_number_reflns 2415 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.0975 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.236 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.047 #----------------------------------------------------------------------------# # 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 C2 C 0.11501(12) 0.4416(3) -0.04596(11) 0.0152(3) Uani 1 1 d . . . C4 C 0.15471(14) 0.7909(3) 0.00136(12) 0.0170(4) Uani 1 1 d . . . C5 C 0.08723(14) 0.7898(3) -0.09217(12) 0.0176(4) Uani 1 1 d . . . C7 C 0.22450(13) 0.4733(3) 0.09797(11) 0.0158(3) Uani 1 1 d . . . C8 C 0.31838(12) 0.5288(2) 0.14021(10) 0.0151(3) Uani 1 1 d . . . C9 C 0.39677(13) 0.6819(3) 0.10059(12) 0.0168(4) Uani 1 1 d . . . C10 C 0.51434(13) 0.6243(3) 0.12285(11) 0.0162(3) Uani 1 1 d . . . C11 C 0.54427(13) 0.4567(3) 0.17666(11) 0.0177(4) Uani 1 1 d . . . C12 C 0.46362(14) 0.3204(3) 0.22446(12) 0.0192(4) Uani 1 1 d . . . C13 C 0.35568(14) 0.4326(3) 0.23310(11) 0.0190(4) Uani 1 1 d . . . C14 C 0.58957(14) 0.7718(3) 0.07512(13) 0.0226(4) Uani 1 1 d . . . C15 C 0.65896(15) 0.3818(3) 0.19433(14) 0.0241(4) Uani 1 1 d . . . N3 N 0.18091(10) 0.5632(2) 0.01211(9) 0.0142(3) Uani 1 1 d . . . O1 O 0.05643(9) 0.56726(17) -0.10737(8) 0.0182(3) Uani 1 1 d . . . O6 O 0.10711(9) 0.24848(17) -0.04628(8) 0.0200(3) Uani 1 1 d . . . H4A H 0.2193(14) 0.880(3) -0.0026(11) 0.018(4) Uiso 1 1 d . . . H4B H 0.1136(14) 0.841(3) 0.0544(13) 0.023(5) Uiso 1 1 d . . . H5A H 0.1292(14) 0.831(3) -0.1466(13) 0.023(5) Uiso 1 1 d . . . H5B H 0.0194(15) 0.874(3) -0.0904(12) 0.023(5) Uiso 1 1 d . . . H7 H 0.1781(13) 0.365(3) 0.1253(12) 0.017(4) Uiso 1 1 d . . . H9A H 0.3849(13) 0.689(3) 0.0296(12) 0.016(4) Uiso 1 1 d . . . H9B H 0.3822(13) 0.830(3) 0.1246(12) 0.021(5) Uiso 1 1 d . . . H12A H 0.4523(14) 0.184(3) 0.1894(12) 0.022(5) Uiso 1 1 d . . . H12B H 0.4952(14) 0.277(3) 0.2869(13) 0.025(5) Uiso 1 1 d . . . H13A H 0.3027(14) 0.333(3) 0.2563(12) 0.023(5) Uiso 1 1 d . . . H13B H 0.3649(14) 0.551(3) 0.2811(12) 0.022(5) Uiso 1 1 d . . . H14A H 0.5832(16) 0.754(3) 0.0064(16) 0.040(6) Uiso 1 1 d . . . H14B H 0.6647(17) 0.750(3) 0.0942(14) 0.036(6) Uiso 1 1 d . . . H14C H 0.5696(15) 0.924(4) 0.0870(14) 0.035(5) Uiso 1 1 d . . . H15A H 0.6690(17) 0.236(4) 0.1699(15) 0.043(6) Uiso 1 1 d . . . H15B H 0.6781(15) 0.368(3) 0.2628(15) 0.034(5) Uiso 1 1 d . . . H15C H 0.7092(16) 0.477(3) 0.1661(14) 0.036(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0135(8) 0.0168(8) 0.0153(8) -0.0017(6) 0.0005(6) 0.0000(6) C4 0.0179(9) 0.0121(8) 0.0205(9) 0.0006(6) -0.0044(7) -0.0002(7) C5 0.0175(9) 0.0136(8) 0.0212(9) 0.0001(6) -0.0029(7) -0.0012(7) C7 0.0184(8) 0.0139(8) 0.0151(8) 0.0025(6) 0.0003(6) 0.0007(7) C8 0.0160(8) 0.0138(8) 0.0154(8) -0.0016(6) 0.0011(6) 0.0029(6) C9 0.0166(8) 0.0156(8) 0.0179(9) 0.0006(7) -0.0006(6) 0.0000(7) C10 0.0149(8) 0.0177(8) 0.0157(8) -0.0048(6) -0.0007(6) -0.0004(6) C11 0.0181(8) 0.0196(8) 0.0150(8) -0.0050(6) -0.0018(6) 0.0027(7) C12 0.0211(9) 0.0188(9) 0.0171(8) 0.0014(7) -0.0040(7) 0.0026(7) C13 0.0200(9) 0.0205(9) 0.0164(8) 0.0022(7) 0.0002(7) -0.0006(7) C14 0.0175(9) 0.0228(10) 0.0273(10) -0.0017(8) 0.0000(7) -0.0019(7) C15 0.0203(9) 0.0275(10) 0.0241(10) -0.0028(8) -0.0017(7) 0.0069(8) N3 0.0146(7) 0.0118(7) 0.0158(7) 0.0008(5) -0.0027(5) -0.0006(5) O1 0.0197(6) 0.0137(6) 0.0204(6) -0.0003(5) -0.0071(5) 0.0004(5) O6 0.0227(6) 0.0125(6) 0.0244(6) -0.0019(5) -0.0028(5) -0.0013(5) #----------------------------------------------------------------------------# # 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 C2 O6 1.2106(19) . ? C2 O1 1.3535(18) . ? C2 N3 1.3595(19) . ? C4 N3 1.465(2) . ? C4 C5 1.529(2) . ? C4 H4A 0.980(18) . ? C4 H4B 0.988(19) . ? C5 O1 1.4546(19) . ? C5 H5A 0.993(18) . ? C5 H5B 0.994(18) . ? C7 C8 1.326(2) . ? C7 N3 1.4210(19) . ? C7 H7 0.984(18) . ? C8 C13 1.498(2) . ? C8 C9 1.500(2) . ? C9 C10 1.521(2) . ? C9 H9A 1.011(17) . ? C9 H9B 1.004(18) . ? C10 C11 1.336(2) . ? C10 C14 1.504(2) . ? C11 C15 1.508(2) . ? C11 C12 1.508(2) . ? C12 C13 1.526(2) . ? C12 H12A 0.992(19) . ? C12 H12B 0.988(19) . ? C13 H13A 0.979(19) . ? C13 H13B 1.011(18) . ? C14 H14A 0.98(2) . ? C14 H14B 0.97(2) . ? C14 H14C 1.00(2) . ? C15 H15A 0.98(2) . ? C15 H15B 0.99(2) . ? C15 H15C 0.97(2) . ? 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 O6 C2 O1 122.35(14) . . ? O6 C2 N3 127.23(15) . . ? O1 C2 N3 110.42(13) . . ? N3 C4 C5 101.14(13) . . ? N3 C4 H4A 112.1(10) . . ? C5 C4 H4A 111.2(10) . . ? N3 C4 H4B 110.6(11) . . ? C5 C4 H4B 112.5(10) . . ? H4A C4 H4B 109.1(14) . . ? O1 C5 C4 105.03(12) . . ? O1 C5 H5A 106.2(11) . . ? C4 C5 H5A 112.9(10) . . ? O1 C5 H5B 106.9(10) . . ? C4 C5 H5B 113.4(10) . . ? H5A C5 H5B 111.7(15) . . ? C8 C7 N3 124.42(15) . . ? C8 C7 H7 121.5(10) . . ? N3 C7 H7 114.1(10) . . ? C7 C8 C13 120.75(15) . . ? C7 C8 C9 124.84(14) . . ? C13 C8 C9 114.39(13) . . ? C8 C9 C10 114.19(13) . . ? C8 C9 H9A 110.0(9) . . ? C10 C9 H9A 107.3(9) . . ? C8 C9 H9B 108.9(10) . . ? C10 C9 H9B 109.7(10) . . ? H9A C9 H9B 106.4(14) . . ? C11 C10 C14 125.38(15) . . ? C11 C10 C9 122.39(15) . . ? C14 C10 C9 112.21(14) . . ? C10 C11 C15 124.50(16) . . ? C10 C11 C12 122.03(15) . . ? C15 C11 C12 113.46(14) . . ? C11 C12 C13 112.91(14) . . ? C11 C12 H12A 109.6(10) . . ? C13 C12 H12A 109.6(10) . . ? C11 C12 H12B 108.8(10) . . ? C13 C12 H12B 111.0(10) . . ? H12A C12 H12B 104.5(15) . . ? C8 C13 C12 109.90(14) . . ? C8 C13 H13A 111.9(10) . . ? C12 C13 H13A 110.3(10) . . ? C8 C13 H13B 108.5(10) . . ? C12 C13 H13B 109.1(10) . . ? H13A C13 H13B 107.0(14) . . ? C10 C14 H14A 111.5(12) . . ? C10 C14 H14B 113.9(12) . . ? H14A C14 H14B 106.4(17) . . ? C10 C14 H14C 109.8(11) . . ? H14A C14 H14C 105.6(17) . . ? H14B C14 H14C 109.3(16) . . ? C11 C15 H15A 111.5(12) . . ? C11 C15 H15B 111.0(11) . . ? H15A C15 H15B 103.9(17) . . ? C11 C15 H15C 111.7(12) . . ? H15A C15 H15C 108.7(17) . . ? H15B C15 H15C 109.7(16) . . ? C2 N3 C7 119.03(13) . . ? C2 N3 C4 110.91(12) . . ? C7 N3 C4 122.98(13) . . ? C2 O1 C5 109.37(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 C4 C5 O1 16.73(16) . . . . ? N3 C7 C8 C13 177.11(14) . . . . ? N3 C7 C8 C9 -4.9(3) . . . . ? C7 C8 C9 C10 -144.23(16) . . . . ? C13 C8 C9 C10 33.84(19) . . . . ? C8 C9 C10 C11 -2.8(2) . . . . ? C8 C9 C10 C14 175.30(14) . . . . ? C14 C10 C11 C15 -3.2(3) . . . . ? C9 C10 C11 C15 174.71(15) . . . . ? C14 C10 C11 C12 178.12(16) . . . . ? C9 C10 C11 C12 -4.0(2) . . . . ? C10 C11 C12 C13 -19.5(2) . . . . ? C15 C11 C12 C13 161.69(14) . . . . ? C7 C8 C13 C12 121.67(17) . . . . ? C9 C8 C13 C12 -56.49(18) . . . . ? C11 C12 C13 C8 48.24(19) . . . . ? O6 C2 N3 C7 -19.1(2) . . . . ? O1 C2 N3 C7 161.37(13) . . . . ? O6 C2 N3 C4 -170.59(17) . . . . ? O1 C2 N3 C4 9.90(18) . . . . ? C8 C7 N3 C2 150.62(16) . . . . ? C8 C7 N3 C4 -61.5(2) . . . . ? C5 C4 N3 C2 -16.52(17) . . . . ? C5 C4 N3 C7 -166.66(14) . . . . ? O6 C2 O1 C5 -177.48(16) . . . . ? N3 C2 O1 C5 2.05(17) . . . . ? C4 C5 O1 C2 -12.33(17) . . . . ? # END of CIF # Attachment '- ccdc_deposit 3dd.cif' data_lm05hff1n _database_code_depnum_ccdc_archive 'CCDC 804844' #TrackingRef '- ccdc_deposit 3dd.cif' _audit_creation_date 2010-06-15T20:03:50-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common HF126A14cris _chemical_formula_moiety 'C12 H17 N O2' _chemical_formula_sum 'C12 H17 N O2' _chemical_formula_weight 207.27 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 13.0268(5) _cell_length_b 6.8021(3) _cell_length_c 12.7876(6) _cell_angle_alpha 90 _cell_angle_beta 105.286(3) _cell_angle_gamma 90 _cell_volume 1093.02(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2996 _cell_measurement_theta_min 3.24 _cell_measurement_theta_max 27.41 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.07 _exptl_crystal_density_diffrn 1.26 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8174 _exptl_absorpt_correction_T_max 0.9834 _exptl_absorpt_process_details 'BRUKER AXS - SADABS' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Bruker X8 kappa APEXII CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_reflns_av_R_equivalents 0.0580 _diffrn_reflns_av_unetI/netI 0.0406 _diffrn_reflns_number 20370 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 27.87 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 2594 _reflns_number_gt 1862 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEXII v2010.3-0 (Bruker AXS, 2010)' _computing_cell_refinement 'APEXII v2010.3-0 (Bruker AXS, 2010)' _computing_data_reduction 'APEXII v2010.3-0 (Bruker AXS, 2010)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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^)+(0.0392P)^2^+0.3061P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refall _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 0.0080(15) _refine_ls_number_reflns 2594 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0701 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1002 _refine_ls_wR_factor_gt 0.0868 _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 0.265 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.044 #----------------------------------------------------------------------------# # 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 C2 C 0.51170(11) 0.7615(2) 0.47592(12) 0.0193(3) Uani 1 1 d . . . C4 C 0.46334(11) 0.7251(2) 0.63730(12) 0.0209(3) Uani 1 1 d . . . C5 C 0.58382(12) 0.7218(3) 0.65754(13) 0.0242(3) Uani 1 1 d . . . C7 C 0.32338(11) 0.7394(2) 0.45525(12) 0.0206(3) Uani 1 1 d . . . C8 C 0.23732(11) 0.6519(2) 0.47072(12) 0.0197(3) Uani 1 1 d . . . C9 C 0.23722(11) 0.4973(2) 0.55490(11) 0.0183(3) Uani 1 1 d . . . C10 C 0.16214(11) 0.3301(2) 0.50632(13) 0.0225(3) Uani 1 1 d . . . C11 C 0.09408(12) 0.3409(3) 0.40967(14) 0.0283(4) Uani 1 1 d . . . C12 C 0.07869(13) 0.5182(3) 0.33703(14) 0.0324(4) Uani 1 1 d . . . C13 C 0.12856(12) 0.7007(2) 0.39913(13) 0.0260(4) Uani 1 1 d . . . C14 C 0.20854(12) 0.5878(2) 0.65377(13) 0.0223(3) Uani 1 1 d . . . C15 C 0.17518(15) 0.1480(3) 0.57492(18) 0.0348(4) Uani 1 1 d . . . N3 N 0.42971(9) 0.71152(17) 0.51892(9) 0.0182(3) Uani 1 1 d . . . O1 O 0.60318(8) 0.77863(15) 0.55526(8) 0.0229(3) Uani 1 1 d . . . O6 O 0.50733(8) 0.78850(16) 0.38110(8) 0.0249(3) Uani 1 1 d . . . H4A H 0.4382(13) 0.614(3) 0.6735(13) 0.032(5) Uiso 1 1 d . . . H4B H 0.4385(13) 0.849(3) 0.6623(13) 0.030(5) Uiso 1 1 d . . . H5A H 0.6139(12) 0.585(3) 0.6751(13) 0.027(4) Uiso 1 1 d . . . H5B H 0.6198(13) 0.818(3) 0.7120(13) 0.028(4) Uiso 1 1 d . . . H7 H 0.3192(12) 0.831(2) 0.3951(13) 0.023(4) Uiso 1 1 d . . . H9 H 0.3088(12) 0.438(2) 0.5810(12) 0.018(4) Uiso 1 1 d . . . H11 H 0.0514(14) 0.228(3) 0.3817(14) 0.034(5) Uiso 1 1 d . . . H12A H 0.1116(14) 0.490(3) 0.2754(14) 0.038(5) Uiso 1 1 d . . . H12B H -0.0006(14) 0.546(3) 0.3019(13) 0.035(5) Uiso 1 1 d . . . H13A H 0.1334(13) 0.809(3) 0.3503(14) 0.029(4) Uiso 1 1 d . . . H13B H 0.0803(13) 0.741(2) 0.4481(13) 0.027(4) Uiso 1 1 d . . . H14A H 0.2627(13) 0.690(3) 0.6906(13) 0.028(4) Uiso 1 1 d . . . H14B H 0.2056(13) 0.484(3) 0.7107(14) 0.037(5) Uiso 1 1 d . . . H14C H 0.1377(14) 0.650(2) 0.6312(13) 0.028(4) Uiso 1 1 d . . . H15A H 0.2468(17) 0.088(3) 0.5841(15) 0.051(6) Uiso 1 1 d . . . H15B H 0.1215(15) 0.046(3) 0.5391(15) 0.050(6) Uiso 1 1 d . . . H15C H 0.1681(16) 0.178(3) 0.6518(18) 0.055(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C2 0.0201(7) 0.0141(7) 0.0249(8) -0.0021(6) 0.0081(6) -0.0006(5) C4 0.0212(7) 0.0230(8) 0.0178(8) -0.0015(6) 0.0041(6) -0.0026(6) C5 0.0218(7) 0.0275(9) 0.0227(8) -0.0027(7) 0.0047(6) -0.0044(6) C7 0.0205(7) 0.0208(8) 0.0200(8) 0.0028(6) 0.0044(6) 0.0012(6) C8 0.0199(7) 0.0189(7) 0.0200(8) -0.0002(6) 0.0045(6) 0.0002(6) C9 0.0165(7) 0.0177(7) 0.0207(8) -0.0001(6) 0.0051(5) -0.0001(6) C10 0.0203(7) 0.0190(8) 0.0306(9) -0.0041(6) 0.0106(6) -0.0010(6) C11 0.0214(8) 0.0295(9) 0.0334(10) -0.0101(7) 0.0063(7) -0.0054(6) C12 0.0230(8) 0.0480(11) 0.0240(9) -0.0023(8) 0.0024(7) -0.0029(7) C13 0.0205(7) 0.0310(9) 0.0256(8) 0.0078(7) 0.0043(6) 0.0007(6) C14 0.0219(8) 0.0236(8) 0.0228(8) -0.0009(7) 0.0082(6) 0.0012(6) C15 0.0327(10) 0.0206(9) 0.0500(12) 0.0026(8) 0.0089(8) -0.0054(7) N3 0.0180(6) 0.0179(6) 0.0186(6) 0.0017(5) 0.0047(5) -0.0017(5) O1 0.0190(5) 0.0243(6) 0.0260(6) -0.0022(5) 0.0071(4) -0.0053(4) O6 0.0266(6) 0.0260(6) 0.0245(6) 0.0020(5) 0.0112(5) -0.0006(4) #----------------------------------------------------------------------------# # 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 C2 O6 1.2127(17) . ? C2 O1 1.3512(17) . ? C2 N3 1.3669(18) . ? C4 N3 1.4637(18) . ? C4 C5 1.522(2) . ? C4 H4A 0.986(18) . ? C4 H4B 0.987(18) . ? C5 O1 1.4482(18) . ? C5 H5A 1.011(17) . ? C5 H5B 0.980(17) . ? C7 C8 1.329(2) . ? C7 N3 1.4222(18) . ? C7 H7 0.979(16) . ? C8 C9 1.505(2) . ? C8 C13 1.507(2) . ? C9 C10 1.522(2) . ? C9 C14 1.538(2) . ? C9 H9 0.989(15) . ? C10 C11 1.319(2) . ? C10 C15 1.501(2) . ? C11 C12 1.503(2) . ? C11 H11 0.963(18) . ? C12 C13 1.524(2) . ? C12 H12A 1.009(18) . ? C12 H12B 1.029(17) . ? C13 H13A 0.977(18) . ? C13 H13B 1.035(17) . ? C14 H14A 1.014(18) . ? C14 H14B 1.021(18) . ? C14 H14C 0.988(17) . ? C15 H15A 1.00(2) . ? C15 H15B 1.01(2) . ? C15 H15C 1.03(2) . ? 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 O6 C2 O1 122.50(12) . . ? O6 C2 N3 127.17(13) . . ? O1 C2 N3 110.32(12) . . ? N3 C4 C5 100.90(11) . . ? N3 C4 H4A 113.0(10) . . ? C5 C4 H4A 111.4(10) . . ? N3 C4 H4B 110.8(10) . . ? C5 C4 H4B 111.7(10) . . ? H4A C4 H4B 108.9(14) . . ? O1 C5 C4 105.06(12) . . ? O1 C5 H5A 107.2(9) . . ? C4 C5 H5A 111.9(9) . . ? O1 C5 H5B 107.4(10) . . ? C4 C5 H5B 112.9(10) . . ? H5A C5 H5B 111.8(13) . . ? C8 C7 N3 125.98(14) . . ? C8 C7 H7 121.8(9) . . ? N3 C7 H7 112.2(9) . . ? C7 C8 C9 125.38(13) . . ? C7 C8 C13 120.38(14) . . ? C9 C8 C13 114.22(12) . . ? C8 C9 C10 110.60(12) . . ? C8 C9 C14 110.76(12) . . ? C10 C9 C14 111.43(12) . . ? C8 C9 H9 110.2(9) . . ? C10 C9 H9 106.4(9) . . ? C14 C9 H9 107.3(8) . . ? C11 C10 C15 122.53(15) . . ? C11 C10 C9 122.79(14) . . ? C15 C10 C9 114.61(14) . . ? C10 C11 C12 124.79(15) . . ? C10 C11 H11 118.9(11) . . ? C12 C11 H11 116.3(11) . . ? C11 C12 C13 111.25(13) . . ? C11 C12 H12A 108.4(10) . . ? C13 C12 H12A 110.5(10) . . ? C11 C12 H12B 111.8(10) . . ? C13 C12 H12B 108.6(10) . . ? H12A C12 H12B 106.1(13) . . ? C8 C13 C12 109.92(13) . . ? C8 C13 H13A 110.2(10) . . ? C12 C13 H13A 111.8(10) . . ? C8 C13 H13B 108.3(9) . . ? C12 C13 H13B 106.9(9) . . ? H13A C13 H13B 109.6(13) . . ? C9 C14 H14A 111.5(9) . . ? C9 C14 H14B 111.9(10) . . ? H14A C14 H14B 107.1(13) . . ? C9 C14 H14C 110.0(10) . . ? H14A C14 H14C 108.8(13) . . ? H14B C14 H14C 107.3(13) . . ? C10 C15 H15A 111.3(12) . . ? C10 C15 H15B 110.1(11) . . ? H15A C15 H15B 106.9(16) . . ? C10 C15 H15C 111.6(12) . . ? H15A C15 H15C 106.6(16) . . ? H15B C15 H15C 110.2(16) . . ? C2 N3 C7 118.87(12) . . ? C2 N3 C4 110.35(12) . . ? C7 N3 C4 124.36(12) . . ? C2 O1 C5 109.03(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 C4 C5 O1 20.14(15) . . . . ? N3 C7 C8 C9 -3.9(2) . . . . ? N3 C7 C8 C13 177.84(14) . . . . ? C7 C8 C9 C10 -135.74(15) . . . . ? C13 C8 C9 C10 42.64(17) . . . . ? C7 C8 C9 C14 100.21(17) . . . . ? C13 C8 C9 C14 -81.41(16) . . . . ? C8 C9 C10 C11 -11.05(19) . . . . ? C14 C9 C10 C11 112.62(16) . . . . ? C8 C9 C10 C15 166.21(13) . . . . ? C14 C9 C10 C15 -70.12(17) . . . . ? C15 C10 C11 C12 -179.21(15) . . . . ? C9 C10 C11 C12 -2.2(2) . . . . ? C10 C11 C12 C13 -15.2(2) . . . . ? C7 C8 C13 C12 117.56(16) . . . . ? C9 C8 C13 C12 -60.91(17) . . . . ? C11 C12 C13 C8 44.37(18) . . . . ? O6 C2 N3 C7 -17.3(2) . . . . ? O1 C2 N3 C7 162.63(12) . . . . ? O6 C2 N3 C4 -170.42(15) . . . . ? O1 C2 N3 C4 9.51(16) . . . . ? C8 C7 N3 C2 160.17(15) . . . . ? C8 C7 N3 C4 -50.7(2) . . . . ? C5 C4 N3 C2 -18.39(16) . . . . ? C5 C4 N3 C7 -169.73(13) . . . . ? O6 C2 O1 C5 -175.36(14) . . . . ? N3 C2 O1 C5 4.70(15) . . . . ? C4 C5 O1 C2 -16.15(16) . . . . ? # END of CIF # Attachment '- ccdc_deposit 3de.cif' data_lm07hff1n _database_code_depnum_ccdc_archive 'CCDC 804845' #TrackingRef '- ccdc_deposit 3de.cif' _audit_creation_date 2010-07-30T11:03:38-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common HF176A10B15 _chemical_formula_moiety 'C12 H17 N O2' _chemical_formula_sum 'C12 H17 N O2' _chemical_formula_weight 207.27 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 16.985(3) _cell_length_b 5.1183(9) _cell_length_c 12.565(2) _cell_angle_alpha 90 _cell_angle_beta 103.577(3) _cell_angle_gamma 90 _cell_volume 1061.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2985 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 28.39 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.77 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6838 _exptl_absorpt_correction_T_max 0.9709 _exptl_absorpt_process_details 'BRUKER AXS - SADABS' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_unetI/netI 0.0316 _diffrn_reflns_number 12765 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 27.1 _diffrn_reflns_theta_full 27.1 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 2343 _reflns_number_gt 1905 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 v2010-7.0 (Bruker AXS, 2010)' _computing_cell_refinement 'APEX2 v2010-7.0 (Bruker AXS, 2010)' _computing_data_reduction 'APEX2 v2010-7.0 (Bruker AXS, 2010)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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^)+(0.0547P)^2^+0.3660P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2343 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.1041 _refine_ls_wR_factor_gt 0.0954 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.299 _refine_diff_density_min -0.256 _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 O1 O 0.03991(6) 0.82670(18) 0.29697(7) 0.0182(2) Uani 1 1 d . . . C2 C 0.03985(8) 0.7178(3) 0.40316(10) 0.0184(3) Uani 1 1 d . . . H2A H -0.0152 0.6592 0.4057 0.022 Uiso 1 1 calc R . . H2B H 0.0585 0.8491 0.4615 0.022 Uiso 1 1 calc R . . C3 C 0.09799(8) 0.4872(3) 0.41764(10) 0.0181(3) Uani 1 1 d . . . H3A H 0.1383 0.4959 0.4886 0.022 Uiso 1 1 calc R . . H3B H 0.0687 0.3188 0.4124 0.022 Uiso 1 1 calc R . . N4 N 0.13621(6) 0.5224(2) 0.32574(8) 0.0158(2) Uani 1 1 d . . . C5 C 0.09386(8) 0.6984(3) 0.25302(11) 0.0164(3) Uani 1 1 d . . . O6 O 0.10156(6) 0.74336(19) 0.16142(7) 0.0208(2) Uani 1 1 d . . . C7 C 0.18209(8) 0.3295(3) 0.28708(11) 0.0164(3) Uani 1 1 d . . . H7 H 0.1665 0.2891 0.2112 0.02 Uiso 1 1 calc R . . C8 C 0.24486(8) 0.1989(3) 0.34614(10) 0.0160(3) Uani 1 1 d . . . C9 C 0.28163(8) 0.2414(3) 0.46643(10) 0.0166(3) Uani 1 1 d . . . H9 H 0.2625 0.414 0.488 0.02 Uiso 1 1 calc R . . C10 C 0.37258(8) 0.2497(3) 0.48675(11) 0.0200(3) Uani 1 1 d . . . H10 H 0.4022 0.3087 0.5563 0.024 Uiso 1 1 calc R . . C11 C 0.41390(8) 0.1806(3) 0.41440(11) 0.0197(3) Uani 1 1 d . . . H11 H 0.4712 0.1971 0.4348 0.024 Uiso 1 1 calc R . . C12 C 0.37638(8) 0.0778(3) 0.30188(11) 0.0177(3) Uani 1 1 d . . . H12 H 0.3767 0.2219 0.2483 0.021 Uiso 1 1 calc R . . C13 C 0.28807(8) -0.0010(3) 0.29332(11) 0.0179(3) Uani 1 1 d . . . H13A H 0.2599 -0.0198 0.2152 0.021 Uiso 1 1 calc R . . H13B H 0.2865 -0.1722 0.3294 0.021 Uiso 1 1 calc R . . C14 C 0.25509(9) 0.0283(3) 0.53668(11) 0.0216(3) Uani 1 1 d . . . H14A H 0.1961 0.0333 0.5262 0.032 Uiso 1 1 calc R . . H14B H 0.2808 0.059 0.614 0.032 Uiso 1 1 calc R . . H14C H 0.2714 -0.1432 0.5147 0.032 Uiso 1 1 calc R . . C15 C 0.42516(9) -0.1492(3) 0.27202(12) 0.0231(3) Uani 1 1 d . . . H15A H 0.4808 -0.0919 0.2759 0.035 Uiso 1 1 calc R . . H15B H 0.4003 -0.2082 0.1975 0.035 Uiso 1 1 calc R . . H15C H 0.4257 -0.2935 0.3234 0.035 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 0.0199(5) 0.0195(5) 0.0154(5) 0.0022(4) 0.0043(4) 0.0034(4) C2 0.0210(7) 0.0210(7) 0.0140(6) 0.0012(5) 0.0057(5) 0.0021(5) C3 0.0199(6) 0.0211(7) 0.0147(6) 0.0017(5) 0.0067(5) 0.0022(5) N4 0.0157(5) 0.0194(6) 0.0127(5) 0.0010(4) 0.0038(4) 0.0015(4) C5 0.0145(6) 0.0178(6) 0.0160(6) -0.0015(5) 0.0016(5) -0.0020(5) O6 0.0237(5) 0.0249(5) 0.0139(5) 0.0031(4) 0.0048(4) 0.0021(4) C7 0.0173(6) 0.0190(6) 0.0136(6) -0.0012(5) 0.0048(5) -0.0006(5) C8 0.0158(6) 0.0175(6) 0.0151(6) -0.0008(5) 0.0045(5) -0.0024(5) C9 0.0184(6) 0.0169(6) 0.0139(6) -0.0012(5) 0.0025(5) 0.0006(5) C10 0.0191(7) 0.0213(7) 0.0168(7) 0.0012(5) -0.0014(5) -0.0009(5) C11 0.0156(6) 0.0210(7) 0.0209(7) 0.0030(5) 0.0010(5) -0.0012(5) C12 0.0184(7) 0.0179(6) 0.0176(6) 0.0022(5) 0.0057(5) 0.0015(5) C13 0.0170(6) 0.0193(7) 0.0172(6) -0.0017(5) 0.0036(5) 0.0008(5) C14 0.0247(7) 0.0227(7) 0.0175(7) 0.0009(5) 0.0053(5) -0.0012(6) C15 0.0204(7) 0.0218(7) 0.0287(8) 0.0009(6) 0.0090(6) 0.0022(6) #----------------------------------------------------------------------------# # 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 O1 C5 1.3465(16) . ? O1 C2 1.4462(15) . ? C2 C3 1.5221(18) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 N4 1.4624(16) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? N4 C5 1.3623(17) . ? N4 C7 1.4128(17) . ? C5 O6 1.2106(16) . ? C7 C8 1.3275(19) . ? C7 H7 0.95 . ? C8 C13 1.5014(18) . ? C8 C9 1.5096(17) . ? C9 C10 1.5060(19) . ? C9 C14 1.5356(18) . ? C9 H9 1 . ? C10 C11 1.320(2) . ? C10 H10 0.95 . ? C11 C12 1.5031(19) . ? C11 H11 0.95 . ? C12 C15 1.5240(19) . ? C12 C13 1.5323(18) . ? C12 H12 1 . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? 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 C5 O1 C2 109.78(10) . . ? O1 C2 C3 105.55(10) . . ? O1 C2 H2A 110.6 . . ? C3 C2 H2A 110.6 . . ? O1 C2 H2B 110.6 . . ? C3 C2 H2B 110.6 . . ? H2A C2 H2B 108.8 . . ? N4 C3 C2 101.89(10) . . ? N4 C3 H3A 111.4 . . ? C2 C3 H3A 111.4 . . ? N4 C3 H3B 111.4 . . ? C2 C3 H3B 111.4 . . ? H3A C3 H3B 109.3 . . ? C5 N4 C7 118.60(11) . . ? C5 N4 C3 110.40(10) . . ? C7 N4 C3 124.64(11) . . ? O6 C5 O1 122.22(12) . . ? O6 C5 N4 127.27(12) . . ? O1 C5 N4 110.51(11) . . ? C8 C7 N4 126.52(12) . . ? C8 C7 H7 116.7 . . ? N4 C7 H7 116.7 . . ? C7 C8 C13 120.51(12) . . ? C7 C8 C9 125.19(12) . . ? C13 C8 C9 114.24(11) . . ? C10 C9 C8 109.91(11) . . ? C10 C9 C14 110.52(11) . . ? C8 C9 C14 111.40(11) . . ? C10 C9 H9 108.3 . . ? C8 C9 H9 108.3 . . ? C14 C9 H9 108.3 . . ? C11 C10 C9 124.44(13) . . ? C11 C10 H10 117.8 . . ? C9 C10 H10 117.8 . . ? C10 C11 C12 124.40(12) . . ? C10 C11 H11 117.8 . . ? C12 C11 H11 117.8 . . ? C11 C12 C15 111.33(11) . . ? C11 C12 C13 110.49(11) . . ? C15 C12 C13 111.22(11) . . ? C11 C12 H12 107.9 . . ? C15 C12 H12 107.9 . . ? C13 C12 H12 107.9 . . ? C8 C13 C12 111.21(11) . . ? C8 C13 H13A 109.4 . . ? C12 C13 H13A 109.4 . . ? C8 C13 H13B 109.4 . . ? C12 C13 H13B 109.4 . . ? H13A C13 H13B 108 . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 O1 C2 C3 -3.74(14) . . . . ? O1 C2 C3 N4 10.27(13) . . . . ? C2 C3 N4 C5 -13.86(14) . . . . ? C2 C3 N4 C7 -165.23(12) . . . . ? C2 O1 C5 O6 175.47(12) . . . . ? C2 O1 C5 N4 -5.19(14) . . . . ? C7 N4 C5 O6 -14.8(2) . . . . ? C3 N4 C5 O6 -168.15(13) . . . . ? C7 N4 C5 O1 165.87(11) . . . . ? C3 N4 C5 O1 12.55(15) . . . . ? C5 N4 C7 C8 157.39(13) . . . . ? C3 N4 C7 C8 -53.4(2) . . . . ? N4 C7 C8 C13 -179.79(12) . . . . ? N4 C7 C8 C9 -2.8(2) . . . . ? C7 C8 C9 C10 -134.80(13) . . . . ? C13 C8 C9 C10 42.32(15) . . . . ? C7 C8 C9 C14 102.36(15) . . . . ? C13 C8 C9 C14 -80.53(14) . . . . ? C8 C9 C10 C11 -11.91(19) . . . . ? C14 C9 C10 C11 111.46(15) . . . . ? C9 C10 C11 C12 -1.4(2) . . . . ? C10 C11 C12 C15 -138.50(14) . . . . ? C10 C11 C12 C13 -14.39(19) . . . . ? C7 C8 C13 C12 117.24(14) . . . . ? C9 C8 C13 C12 -60.03(15) . . . . ? C11 C12 C13 C8 43.09(15) . . . . ? C15 C12 C13 C8 167.25(11) . . . . ? # END of CIF # Attachment '- ccdc_deposit 3df.cif' data_lm8hff1n _database_code_depnum_ccdc_archive 'CCDC 804846' #TrackingRef '- ccdc_deposit 3df.cif' _audit_creation_date 2010-09-03T12:38:17-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H31 N1 O3 Si1' _chemical_formula_sum 'C18 H31 N O3 Si' _chemical_formula_weight 337.53 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' _space_group_IT_number 14 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.3695(5) _cell_length_b 47.261(3) _cell_length_c 11.0525(6) _cell_angle_alpha 90 _cell_angle_beta 90.470(4) _cell_angle_gamma 90 _cell_volume 3849.4(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1714 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 17.03 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.165 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_absorpt_correction_T_min 0.6105 _exptl_absorpt_correction_T_max 0.7451 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromador graphite _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'BRUKER APPEX-II CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_reflns_av_R_equivalents 0.1455 _diffrn_reflns_av_unetI/netI 0.1152 _diffrn_reflns_number 34914 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 47 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 20.81 _diffrn_reflns_theta_full 20.81 _diffrn_measured_fraction_theta_full 0.968 _diffrn_measured_fraction_theta_max 0.968 _reflns_number_total 3916 _reflns_number_gt 2453 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APPEX2 (BRUKER AXS, 2005)' _computing_cell_refinement 'APPEX2 (BRUKER AXS, 2005)' _computing_data_reduction 'APPEX2 (BRUKER AXS, 2005)' _computing_structure_solution 'SIR2004 (Giacovazzo et al, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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^)+(0.0479P)^2^+10.2207P] 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 0.0065(6) _refine_ls_number_reflns 3916 _refine_ls_number_parameters 428 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1441 _refine_ls_R_factor_gt 0.0846 _refine_ls_wR_factor_ref 0.1836 _refine_ls_wR_factor_gt 0.159 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.293 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.067 #----------------------------------------------------------------------------# # 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' Si Si 0.0817 0.0704 '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 C1 C 0.6730(10) 0.10437(15) 0.4775(7) 0.029(2) Uani 1 1 d . . . H1 H 0.7687 0.0913 0.4466 0.035 Uiso 1 1 calc R . . C2 C 0.5104(11) 0.10305(15) 0.3901(6) 0.030(2) Uani 1 1 d . . . H2A H 0.4262 0.1188 0.408 0.036 Uiso 1 1 calc R . . H2B H 0.5535 0.1054 0.3061 0.036 Uiso 1 1 calc R . . C3 C 0.4103(10) 0.07530(16) 0.4004(6) 0.023(2) Uani 1 1 d . . . C4 C 0.3388(10) 0.06961(16) 0.5253(6) 0.029(2) Uani 1 1 d . . . H4 H 0.3235 0.0487 0.5347 0.035 Uiso 1 1 calc R . . C4B C 0.1507(11) 0.0837(2) 0.5399(7) 0.056(3) Uani 1 1 d . . . H4B1 H 0.1098 0.0814 0.6235 0.084 Uiso 1 1 calc R . . H4B2 H 0.0633 0.0748 0.4847 0.084 Uiso 1 1 calc R . . H4B3 H 0.16 0.1039 0.5208 0.084 Uiso 1 1 calc R . . C5 C 0.4684(11) 0.07969(16) 0.6211(7) 0.032(2) Uani 1 1 d . . . H5 H 0.4411 0.0753 0.7028 0.038 Uiso 1 1 calc R . . C6 C 0.6180(12) 0.09422(15) 0.6001(7) 0.032(2) Uani 1 1 d . . . H6 H 0.6953 0.0985 0.6668 0.038 Uiso 1 1 calc R . . C8 C 0.3969(10) 0.05889(15) 0.3028(7) 0.026(2) Uani 1 1 d . . . H8 H 0.4476 0.0665 0.231 0.031 Uiso 1 1 calc R . . N9 N 0.3176(8) 0.03175(13) 0.2911(5) 0.0260(17) Uani 1 1 d . . . C10 C 0.2876(10) 0.02049(16) 0.1798(8) 0.024(2) Uani 1 1 d . . . O10B O 0.3224(7) 0.03066(10) 0.0832(5) 0.0294(14) Uani 1 1 d . . . O11 O 0.2190(7) -0.00606(10) 0.1914(4) 0.0317(14) Uani 1 1 d . . . C12 C 0.2124(10) -0.01402(15) 0.3159(6) 0.029(2) Uani 1 1 d . . . H12A H 0.2988 -0.0296 0.3326 0.035 Uiso 1 1 calc R . . H12B H 0.0889 -0.0204 0.3373 0.035 Uiso 1 1 calc R . . C13 C 0.2644(10) 0.01228(15) 0.3887(6) 0.029(2) Uani 1 1 d . . . H13A H 0.1602 0.0197 0.4349 0.035 Uiso 1 1 calc R . . H13B H 0.3668 0.0084 0.4449 0.035 Uiso 1 1 calc R . . C14 C 0.7539(12) 0.13406(16) 0.4846(7) 0.043(2) Uani 1 1 d . . . H14A H 0.857 0.134 0.5425 0.052 Uiso 1 1 calc R . . H14B H 0.8015 0.1393 0.4042 0.052 Uiso 1 1 calc R . . O15 O 0.6267(7) 0.15463(10) 0.5212(4) 0.0374(15) Uani 1 1 d . . . Si16 Si 0.5984(3) 0.17035(5) 0.6528(2) 0.0361(7) Uani 1 1 d . . . C17 C 0.3562(12) 0.16405(19) 0.6940(8) 0.061(3) Uani 1 1 d . . . H17A H 0.2767 0.1744 0.6378 0.091 Uiso 1 1 calc R . . H17B H 0.3354 0.1707 0.7767 0.091 Uiso 1 1 calc R . . H17C H 0.3296 0.1438 0.6891 0.091 Uiso 1 1 calc R . . C18 C 0.7543(13) 0.15676(17) 0.7727(7) 0.056(3) Uani 1 1 d . . . H18A H 0.7217 0.1372 0.7925 0.084 Uiso 1 1 calc R . . H18B H 0.744 0.1686 0.8451 0.084 Uiso 1 1 calc R . . H18C H 0.8795 0.1573 0.7435 0.084 Uiso 1 1 calc R . . C19 C 0.6422(11) 0.20885(16) 0.6275(7) 0.033(2) Uani 1 1 d . . . C20 C 0.5287(13) 0.21948(17) 0.5214(8) 0.056(3) Uani 1 1 d . . . H20A H 0.562 0.2391 0.5033 0.084 Uiso 1 1 calc R . . H20B H 0.3998 0.2186 0.5421 0.084 Uiso 1 1 calc R . . H20C H 0.5513 0.2076 0.4504 0.084 Uiso 1 1 calc R . . C21 C 0.8425(12) 0.21309(18) 0.5989(8) 0.056(3) Uani 1 1 d . . . H21A H 0.874 0.202 0.5272 0.085 Uiso 1 1 calc R . . H21B H 0.9167 0.2069 0.6679 0.085 Uiso 1 1 calc R . . H21C H 0.8656 0.2332 0.5831 0.085 Uiso 1 1 calc R . . C22 C 0.5969(12) 0.22629(16) 0.7413(7) 0.047(3) Uani 1 1 d . . . H22A H 0.6222 0.2463 0.726 0.07 Uiso 1 1 calc R . . H22B H 0.6715 0.2197 0.8095 0.07 Uiso 1 1 calc R . . H22C H 0.4683 0.2239 0.7606 0.07 Uiso 1 1 calc R . . C31 C 0.1853(10) 0.10271(15) 0.0373(6) 0.026(2) Uani 1 1 d . . . H31 H 0.2741 0.0875 0.0587 0.031 Uiso 1 1 calc R . . C32 C 0.0251(10) 0.10046(15) 0.1244(6) 0.028(2) Uani 1 1 d . . . H32A H 0.0707 0.1014 0.2088 0.034 Uiso 1 1 calc R . . H32B H -0.0577 0.1167 0.1112 0.034 Uiso 1 1 calc R . . C33 C -0.0783(10) 0.07316(15) 0.1058(6) 0.022(2) Uani 1 1 d . . . C34 C -0.1481(10) 0.06798(15) -0.0211(6) 0.027(2) Uani 1 1 d . . . H34 H -0.1498 0.0471 -0.0362 0.032 Uiso 1 1 calc R . . C34B C -0.3441(10) 0.07944(17) -0.0344(6) 0.035(2) Uani 1 1 d . . . H34A H -0.4246 0.0689 0.0195 0.053 Uiso 1 1 calc R . . H34B H -0.3854 0.0771 -0.1183 0.053 Uiso 1 1 calc R . . H34C H -0.3462 0.0995 -0.0127 0.053 Uiso 1 1 calc R . . C35 C -0.0289(12) 0.08185(16) -0.1145(7) 0.032(2) Uani 1 1 d . . . H35 H -0.0604 0.0794 -0.1973 0.038 Uiso 1 1 calc R . . C36 C 0.1164(12) 0.09716(16) -0.0886(7) 0.033(2) Uani 1 1 d . . . H36 H 0.1816 0.1052 -0.154 0.039 Uiso 1 1 calc R . . C38 C -0.1036(10) 0.05679(16) 0.2012(7) 0.025(2) Uani 1 1 d . . . H38 H -0.0571 0.0642 0.2751 0.03 Uiso 1 1 calc R . . N39 N -0.1892(8) 0.02991(12) 0.2113(5) 0.0204(16) Uani 1 1 d . . . C40 C -0.2215(11) 0.01825(17) 0.3201(7) 0.027(2) Uani 1 1 d . . . O40B O -0.1933(7) 0.02870(10) 0.4186(5) 0.0339(15) Uani 1 1 d . . . O41 O -0.2911(7) -0.00828(11) 0.3066(4) 0.0322(14) Uani 1 1 d . . . C42 C -0.2942(11) -0.01578(15) 0.1788(6) 0.031(2) Uani 1 1 d . . . H42A H -0.4186 -0.0211 0.1529 0.037 Uiso 1 1 calc R . . H42B H -0.2122 -0.032 0.1634 0.037 Uiso 1 1 calc R . . C43 C -0.2301(10) 0.01059(14) 0.1097(6) 0.023(2) Uani 1 1 d . . . H43A H -0.1208 0.0066 0.0612 0.028 Uiso 1 1 calc R . . H43B H -0.3269 0.0182 0.0564 0.028 Uiso 1 1 calc R . . C44 C 0.2807(10) 0.13086(15) 0.0505(7) 0.029(2) Uani 1 1 d . . . H44A H 0.3305 0.1325 0.1337 0.035 Uiso 1 1 calc R . . H44B H 0.3836 0.1316 -0.0064 0.035 Uiso 1 1 calc R . . O45 O 0.1635(6) 0.15394(9) 0.0275(4) 0.0272(13) Uani 1 1 d . . . Si46 Si 0.2029(3) 0.18662(5) 0.0737(2) 0.0307(7) Uani 1 1 d . . . C47 C 0.4505(10) 0.19313(17) 0.0764(7) 0.046(2) Uani 1 1 d . . . H47A H 0.5067 0.182 0.1414 0.069 Uiso 1 1 calc R . . H47B H 0.4735 0.2133 0.0907 0.069 Uiso 1 1 calc R . . H47C H 0.5025 0.1876 -0.0014 0.069 Uiso 1 1 calc R . . C48 C 0.0902(11) 0.21015(16) -0.0372(7) 0.041(2) Uani 1 1 d . . . H48A H 0.1395 0.2066 -0.1178 0.061 Uiso 1 1 calc R . . H48B H 0.1118 0.2299 -0.0145 0.061 Uiso 1 1 calc R . . H48C H -0.0406 0.2064 -0.0379 0.061 Uiso 1 1 calc R . . C49 C 0.1075(11) 0.19199(15) 0.2281(7) 0.029(2) Uani 1 1 d . . . C50 C -0.1014(11) 0.18836(17) 0.2205(7) 0.044(2) Uani 1 1 d . . . H50A H -0.1303 0.1697 0.1869 0.065 Uiso 1 1 calc R . . H50B H -0.153 0.2031 0.1682 0.065 Uiso 1 1 calc R . . H50C H -0.1528 0.19 0.3017 0.065 Uiso 1 1 calc R . . C51 C 0.1469(11) 0.22198(15) 0.2733(6) 0.038(2) Uani 1 1 d . . . H51A H 0.0857 0.225 0.3506 0.057 Uiso 1 1 calc R . . H51B H 0.1021 0.2357 0.2138 0.057 Uiso 1 1 calc R . . H51C H 0.278 0.2244 0.2845 0.057 Uiso 1 1 calc R . . C52 C 0.1850(11) 0.17070(17) 0.3184(7) 0.043(2) Uani 1 1 d . . . H52A H 0.317 0.173 0.3239 0.064 Uiso 1 1 calc R . . H52B H 0.1562 0.1515 0.2914 0.064 Uiso 1 1 calc R . . H52C H 0.1315 0.174 0.3981 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 C1 0.015(5) 0.029(5) 0.044(6) -0.001(4) 0.001(5) 0.003(4) C2 0.039(6) 0.036(5) 0.014(4) -0.002(4) 0.007(4) -0.002(4) C3 0.019(5) 0.038(5) 0.012(5) 0.004(4) -0.001(4) 0.007(4) C4 0.025(6) 0.043(5) 0.020(5) -0.003(4) 0.003(4) -0.011(4) C4B 0.028(6) 0.106(8) 0.035(6) -0.019(5) 0.008(5) -0.005(6) C5 0.036(6) 0.038(5) 0.023(5) -0.001(4) -0.001(5) 0.000(5) C6 0.032(6) 0.030(5) 0.034(5) -0.003(4) -0.010(5) 0.005(5) C8 0.026(5) 0.027(5) 0.024(5) 0.006(4) 0.006(4) 0.005(4) N9 0.024(4) 0.033(4) 0.021(4) -0.003(3) 0.006(3) 0.001(3) C10 0.016(5) 0.027(5) 0.030(6) 0.005(5) 0.011(4) 0.002(4) O10B 0.033(4) 0.033(3) 0.023(3) 0.000(3) 0.007(3) 0.003(3) O11 0.036(4) 0.035(4) 0.024(3) 0.002(3) 0.008(3) -0.005(3) C12 0.027(5) 0.035(5) 0.026(5) 0.000(4) 0.009(4) -0.002(4) C13 0.024(5) 0.036(5) 0.026(5) 0.000(4) 0.003(4) -0.006(4) C14 0.043(6) 0.043(6) 0.043(6) -0.006(4) 0.009(5) -0.011(5) O15 0.042(4) 0.037(3) 0.033(3) -0.008(3) 0.003(3) 0.000(3) Si16 0.0427(17) 0.0329(15) 0.0328(14) -0.0012(12) 0.0080(13) -0.0021(12) C17 0.057(7) 0.076(7) 0.050(6) -0.014(5) 0.031(5) -0.021(6) C18 0.075(8) 0.052(6) 0.042(6) -0.004(5) -0.018(6) 0.011(6) C19 0.033(6) 0.040(5) 0.027(5) -0.014(4) 0.005(5) 0.001(4) C20 0.066(8) 0.048(6) 0.055(6) -0.001(5) -0.011(6) 0.004(5) C21 0.067(8) 0.057(7) 0.045(6) -0.011(5) 0.007(6) -0.020(6) C22 0.059(7) 0.039(6) 0.042(6) 0.004(4) 0.001(5) 0.003(5) C31 0.019(5) 0.028(5) 0.029(5) 0.003(4) 0.007(4) -0.004(4) C32 0.027(5) 0.029(5) 0.028(5) -0.001(4) 0.005(4) -0.001(4) C33 0.014(5) 0.036(5) 0.018(5) 0.002(4) 0.008(4) -0.001(4) C34 0.026(6) 0.031(5) 0.024(5) 0.008(4) 0.007(4) -0.002(4) C34B 0.027(6) 0.061(6) 0.018(5) 0.013(4) 0.004(4) 0.000(5) C35 0.033(6) 0.031(5) 0.032(5) -0.002(4) 0.002(5) 0.004(5) C36 0.038(6) 0.037(5) 0.023(5) 0.006(4) 0.017(5) 0.012(5) C38 0.019(5) 0.037(5) 0.019(5) -0.008(4) 0.004(4) 0.004(4) N39 0.023(4) 0.028(4) 0.010(4) -0.004(3) 0.005(3) 0.002(3) C40 0.024(6) 0.039(6) 0.019(6) 0.003(5) 0.016(4) 0.012(4) O40B 0.040(4) 0.043(4) 0.019(3) 0.001(3) 0.001(3) -0.003(3) O41 0.040(4) 0.030(3) 0.027(3) 0.003(3) 0.010(3) -0.006(3) C42 0.038(6) 0.034(5) 0.022(5) -0.001(4) 0.007(4) 0.002(4) C43 0.012(5) 0.026(5) 0.032(5) 0.008(4) 0.010(4) 0.002(4) C44 0.028(5) 0.030(5) 0.029(5) -0.003(4) 0.017(4) 0.000(4) O45 0.020(3) 0.021(3) 0.040(3) -0.002(2) 0.006(3) 0.003(3) Si46 0.0235(15) 0.0348(15) 0.0339(14) 0.0013(11) 0.0060(12) -0.0002(12) C47 0.031(6) 0.051(6) 0.055(6) -0.004(5) 0.007(5) -0.010(5) C48 0.048(6) 0.040(5) 0.035(5) 0.009(4) 0.004(5) 0.005(5) C49 0.028(6) 0.029(5) 0.030(5) 0.001(4) 0.008(4) -0.002(4) C50 0.034(6) 0.048(6) 0.049(6) -0.007(5) 0.007(5) -0.004(5) C51 0.043(6) 0.046(6) 0.026(5) 0.000(4) -0.001(4) -0.006(5) C52 0.044(6) 0.044(5) 0.040(5) 0.001(5) 0.000(5) -0.002(5) #----------------------------------------------------------------------------# # 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 C1 C6 1.496(10) . ? C1 C14 1.526(10) . ? C1 C2 1.535(10) . ? C1 H1 1 . ? C2 C3 1.509(10) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C8 1.332(9) . ? C3 C4 1.506(9) . ? C4 C5 1.497(10) . ? C4 C4B 1.548(10) . ? C4 H4 1 . ? C4B H4B1 0.98 . ? C4B H4B2 0.98 . ? C4B H4B3 0.98 . ? C5 C6 1.321(10) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C8 N9 1.415(9) . ? C8 H8 0.95 . ? N9 C10 1.357(9) . ? N9 C13 1.473(9) . ? C10 O10B 1.200(8) . ? C10 O11 1.359(8) . ? O11 C12 1.427(8) . ? C12 C13 1.528(9) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 O15 1.412(9) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? O15 Si16 1.648(5) . ? Si16 C18 1.861(8) . ? Si16 C19 1.869(8) . ? Si16 C17 1.870(8) . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? C19 C20 1.521(10) . ? C19 C21 1.526(11) . ? C19 C22 1.542(10) . ? C20 H20A 0.98 . ? C20 H20B 0.98 . ? C20 H20C 0.98 . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? C22 H22A 0.98 . ? C22 H22B 0.98 . ? C22 H22C 0.98 . ? C31 C36 1.501(10) . ? C31 C44 1.511(9) . ? C31 C32 1.532(9) . ? C31 H31 1 . ? C32 C33 1.512(9) . ? C32 H32A 0.99 . ? C32 H32B 0.99 . ? C33 C38 1.322(9) . ? C33 C34 1.510(9) . ? C34 C35 1.511(10) . ? C34 C34B 1.548(10) . ? C34 H34 1 . ? C34B H34A 0.98 . ? C34B H34B 0.98 . ? C34B H34C 0.98 . ? C35 C36 1.322(10) . ? C35 H35 0.95 . ? C36 H36 0.95 . ? C38 N39 1.423(9) . ? C38 H38 0.95 . ? N39 C40 1.346(9) . ? N39 C43 1.477(8) . ? C40 O40B 1.212(8) . ? C40 O41 1.362(9) . ? O41 C42 1.456(8) . ? C42 C43 1.538(9) . ? C42 H42A 0.99 . ? C42 H42B 0.99 . ? C43 H43A 0.99 . ? C43 H43B 0.99 . ? C44 O45 1.413(8) . ? C44 H44A 0.99 . ? C44 H44B 0.99 . ? O45 Si46 1.652(5) . ? Si46 C48 1.846(7) . ? Si46 C47 1.851(8) . ? Si46 C49 1.868(7) . ? C47 H47A 0.98 . ? C47 H47B 0.98 . ? C47 H47C 0.98 . ? C48 H48A 0.98 . ? C48 H48B 0.98 . ? C48 H48C 0.98 . ? C49 C52 1.525(10) . ? C49 C51 1.530(9) . ? C49 C50 1.551(10) . ? C50 H50A 0.98 . ? C50 H50B 0.98 . ? C50 H50C 0.98 . ? C51 H51A 0.98 . ? C51 H51B 0.98 . ? C51 H51C 0.98 . ? C52 H52A 0.98 . ? C52 H52B 0.98 . ? C52 H52C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C14 110.9(6) . . ? C6 C1 C2 110.0(6) . . ? C14 C1 C2 111.8(6) . . ? C6 C1 H1 108 . . ? C14 C1 H1 108 . . ? C2 C1 H1 108 . . ? C3 C2 C1 111.5(6) . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 108 . . ? C8 C3 C4 127.9(7) . . ? C8 C3 C2 118.5(6) . . ? C4 C3 C2 113.5(6) . . ? C5 C4 C3 111.4(6) . . ? C5 C4 C4B 110.8(6) . . ? C3 C4 C4B 109.8(6) . . ? C5 C4 H4 108.2 . . ? C3 C4 H4 108.2 . . ? C4B C4 H4 108.2 . . ? C4 C4B H4B1 109.5 . . ? C4 C4B H4B2 109.5 . . ? H4B1 C4B H4B2 109.5 . . ? C4 C4B H4B3 109.5 . . ? H4B1 C4B H4B3 109.5 . . ? H4B2 C4B H4B3 109.5 . . ? C6 C5 C4 124.7(7) . . ? C6 C5 H5 117.6 . . ? C4 C5 H5 117.6 . . ? C5 C6 C1 124.0(8) . . ? C5 C6 H6 118 . . ? C1 C6 H6 118 . . ? C3 C8 N9 129.0(7) . . ? C3 C8 H8 115.5 . . ? N9 C8 H8 115.5 . . ? C10 N9 C8 120.1(6) . . ? C10 N9 C13 112.1(6) . . ? C8 N9 C13 127.7(6) . . ? O10B C10 N9 128.0(7) . . ? O10B C10 O11 122.4(7) . . ? N9 C10 O11 109.5(7) . . ? C10 O11 C12 110.5(6) . . ? O11 C12 C13 106.4(5) . . ? O11 C12 H12A 110.4 . . ? C13 C12 H12A 110.4 . . ? O11 C12 H12B 110.4 . . ? C13 C12 H12B 110.4 . . ? H12A C12 H12B 108.6 . . ? N9 C13 C12 100.9(5) . . ? N9 C13 H13A 111.6 . . ? C12 C13 H13A 111.6 . . ? N9 C13 H13B 111.6 . . ? C12 C13 H13B 111.6 . . ? H13A C13 H13B 109.4 . . ? O15 C14 C1 112.8(7) . . ? O15 C14 H14A 109 . . ? C1 C14 H14A 109 . . ? O15 C14 H14B 109 . . ? C1 C14 H14B 109 . . ? H14A C14 H14B 107.8 . . ? C14 O15 Si16 130.7(5) . . ? O15 Si16 C18 113.0(3) . . ? O15 Si16 C19 106.5(3) . . ? C18 Si16 C19 109.6(4) . . ? O15 Si16 C17 105.7(3) . . ? C18 Si16 C17 110.9(4) . . ? C19 Si16 C17 111.0(4) . . ? Si16 C17 H17A 109.5 . . ? Si16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? Si16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? Si16 C18 H18A 109.5 . . ? Si16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? Si16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C21 108.9(7) . . ? C20 C19 C22 109.3(7) . . ? C21 C19 C22 108.4(7) . . ? C20 C19 Si16 110.0(5) . . ? C21 C19 Si16 109.1(6) . . ? C22 C19 Si16 111.1(5) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C36 C31 C44 113.4(6) . . ? C36 C31 C32 108.3(6) . . ? C44 C31 C32 111.1(6) . . ? C36 C31 H31 108 . . ? C44 C31 H31 108 . . ? C32 C31 H31 108 . . ? C33 C32 C31 111.4(6) . . ? C33 C32 H32A 109.4 . . ? C31 C32 H32A 109.4 . . ? C33 C32 H32B 109.4 . . ? C31 C32 H32B 109.4 . . ? H32A C32 H32B 108 . . ? C38 C33 C34 126.6(7) . . ? C38 C33 C32 117.8(7) . . ? C34 C33 C32 115.6(6) . . ? C33 C34 C35 111.6(6) . . ? C33 C34 C34B 110.0(6) . . ? C35 C34 C34B 109.3(6) . . ? C33 C34 H34 108.6 . . ? C35 C34 H34 108.6 . . ? C34B C34 H34 108.6 . . ? C34 C34B H34A 109.5 . . ? C34 C34B H34B 109.5 . . ? H34A C34B H34B 109.5 . . ? C34 C34B H34C 109.5 . . ? H34A C34B H34C 109.5 . . ? H34B C34B H34C 109.5 . . ? C36 C35 C34 124.3(7) . . ? C36 C35 H35 117.8 . . ? C34 C35 H35 117.8 . . ? C35 C36 C31 124.3(7) . . ? C35 C36 H36 117.8 . . ? C31 C36 H36 117.8 . . ? C33 C38 N39 130.6(7) . . ? C33 C38 H38 114.7 . . ? N39 C38 H38 114.7 . . ? C40 N39 C38 121.2(6) . . ? C40 N39 C43 112.9(6) . . ? C38 N39 C43 125.5(6) . . ? O40B C40 N39 127.3(8) . . ? O40B C40 O41 122.4(7) . . ? N39 C40 O41 110.3(7) . . ? C40 O41 C42 109.5(5) . . ? O41 C42 C43 106.3(5) . . ? O41 C42 H42A 110.5 . . ? C43 C42 H42A 110.5 . . ? O41 C42 H42B 110.5 . . ? C43 C42 H42B 110.5 . . ? H42A C42 H42B 108.7 . . ? N39 C43 C42 100.7(5) . . ? N39 C43 H43A 111.6 . . ? C42 C43 H43A 111.6 . . ? N39 C43 H43B 111.6 . . ? C42 C43 H43B 111.6 . . ? H43A C43 H43B 109.4 . . ? O45 C44 C31 112.3(6) . . ? O45 C44 H44A 109.1 . . ? C31 C44 H44A 109.1 . . ? O45 C44 H44B 109.1 . . ? C31 C44 H44B 109.1 . . ? H44A C44 H44B 107.9 . . ? C44 O45 Si46 124.1(4) . . ? O45 Si46 C48 106.3(3) . . ? O45 Si46 C47 109.3(3) . . ? C48 Si46 C47 110.4(4) . . ? O45 Si46 C49 110.1(3) . . ? C48 Si46 C49 110.7(4) . . ? C47 Si46 C49 109.9(4) . . ? Si46 C47 H47A 109.5 . . ? Si46 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? Si46 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? Si46 C48 H48A 109.5 . . ? Si46 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? Si46 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C52 C49 C51 109.2(6) . . ? C52 C49 C50 109.2(6) . . ? C51 C49 C50 107.8(6) . . ? C52 C49 Si46 111.5(5) . . ? C51 C49 Si46 110.7(5) . . ? C50 C49 Si46 108.4(5) . . ? C49 C50 H50A 109.5 . . ? C49 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C49 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C49 C51 H51A 109.5 . . ? C49 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C49 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C49 C52 H52A 109.5 . . ? C49 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C49 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -45.9(8) . . . . ? C14 C1 C2 C3 -169.6(6) . . . . ? C1 C2 C3 C8 -120.2(7) . . . . ? C1 C2 C3 C4 59.0(8) . . . . ? C8 C3 C4 C5 141.7(8) . . . . ? C2 C3 C4 C5 -37.4(9) . . . . ? C8 C3 C4 C4B -95.1(9) . . . . ? C2 C3 C4 C4B 85.8(8) . . . . ? C3 C4 C5 C6 6.2(11) . . . . ? C4B C4 C5 C6 -116.4(9) . . . . ? C4 C5 C6 C1 4.3(12) . . . . ? C14 C1 C6 C5 140.2(8) . . . . ? C2 C1 C6 C5 16.0(10) . . . . ? C4 C3 C8 N9 -2.0(13) . . . . ? C2 C3 C8 N9 177.1(7) . . . . ? C3 C8 N9 C10 168.0(8) . . . . ? C3 C8 N9 C13 -14.1(12) . . . . ? C8 N9 C10 O10B 1.0(12) . . . . ? C13 N9 C10 O10B -177.2(7) . . . . ? C8 N9 C10 O11 177.1(6) . . . . ? C13 N9 C10 O11 -1.1(8) . . . . ? O10B C10 O11 C12 172.6(7) . . . . ? N9 C10 O11 C12 -3.8(8) . . . . ? C10 O11 C12 C13 6.8(8) . . . . ? C10 N9 C13 C12 4.9(8) . . . . ? C8 N9 C13 C12 -173.1(7) . . . . ? O11 C12 C13 N9 -6.8(7) . . . . ? C6 C1 C14 O15 -65.1(9) . . . . ? C2 C1 C14 O15 58.1(9) . . . . ? C1 C14 O15 Si16 102.8(7) . . . . ? C14 O15 Si16 C18 -3.7(7) . . . . ? C14 O15 Si16 C19 116.7(6) . . . . ? C14 O15 Si16 C17 -125.2(7) . . . . ? O15 Si16 C19 C20 51.8(6) . . . . ? C18 Si16 C19 C20 174.4(6) . . . . ? C17 Si16 C19 C20 -62.7(6) . . . . ? O15 Si16 C19 C21 -67.5(6) . . . . ? C18 Si16 C19 C21 55.1(6) . . . . ? C17 Si16 C19 C21 177.9(5) . . . . ? O15 Si16 C19 C22 173.0(6) . . . . ? C18 Si16 C19 C22 -64.4(7) . . . . ? C17 Si16 C19 C22 58.5(7) . . . . ? C36 C31 C32 C33 51.1(8) . . . . ? C44 C31 C32 C33 176.2(6) . . . . ? C31 C32 C33 C38 126.1(7) . . . . ? C31 C32 C33 C34 -55.9(8) . . . . ? C38 C33 C34 C35 -153.1(7) . . . . ? C32 C33 C34 C35 29.1(9) . . . . ? C38 C33 C34 C34B 85.4(9) . . . . ? C32 C33 C34 C34B -92.4(7) . . . . ? C33 C34 C35 C36 -1.4(11) . . . . ? C34B C34 C35 C36 120.5(8) . . . . ? C34 C35 C36 C31 0.7(12) . . . . ? C44 C31 C36 C35 -149.7(8) . . . . ? C32 C31 C36 C35 -25.9(10) . . . . ? C34 C33 C38 N39 4.5(13) . . . . ? C32 C33 C38 N39 -177.8(7) . . . . ? C33 C38 N39 C40 -171.5(8) . . . . ? C33 C38 N39 C43 16.7(12) . . . . ? C38 N39 C40 O40B 3.9(12) . . . . ? C43 N39 C40 O40B 176.7(7) . . . . ? C38 N39 C40 O41 -175.3(6) . . . . ? C43 N39 C40 O41 -2.4(9) . . . . ? O40B C40 O41 C42 -175.0(7) . . . . ? N39 C40 O41 C42 4.2(8) . . . . ? C40 O41 C42 C43 -4.2(8) . . . . ? C40 N39 C43 C42 -0.2(8) . . . . ? C38 N39 C43 C42 172.2(6) . . . . ? O41 C42 C43 N39 2.6(7) . . . . ? C36 C31 C44 O45 63.1(8) . . . . ? C32 C31 C44 O45 -59.2(8) . . . . ? C31 C44 O45 Si46 160.2(5) . . . . ? C44 O45 Si46 C48 151.4(5) . . . . ? C44 O45 Si46 C47 32.2(6) . . . . ? C44 O45 Si46 C49 -88.6(6) . . . . ? O45 Si46 C49 C52 56.9(6) . . . . ? C48 Si46 C49 C52 174.2(5) . . . . ? C47 Si46 C49 C52 -63.5(6) . . . . ? O45 Si46 C49 C51 178.7(5) . . . . ? C48 Si46 C49 C51 -64.1(7) . . . . ? C47 Si46 C49 C51 58.2(6) . . . . ? O45 Si46 C49 C50 -63.3(6) . . . . ? C48 Si46 C49 C50 54.0(6) . . . . ? C47 Si46 C49 C50 176.2(5) . . . . ? # END of CIF # Attachment '- ccdc_deposit 3di.cif' data_lm09hff1n _database_code_depnum_ccdc_archive 'CCDC 804847' #TrackingRef '- ccdc_deposit 3di.cif' _audit_creation_date 2010-08-24T10:47:40-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C17 H19 N1 O2' _chemical_formula_sum 'C17 H19 N O2' _chemical_formula_weight 269.33 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'P b c a' _space_group_name_Hall '-P 2ac 2ab' _space_group_IT_number 61 loop_ _space_group_symop_operation_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' '-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 7.7628(9) _cell_length_b 11.1348(13) _cell_length_c 32.262(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2788.7(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5207 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 26.29 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_absorpt_correction_T_min 0.8931 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromador graphite _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'BRUKER APPEX-II CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_reflns_av_R_equivalents 0.0458 _diffrn_reflns_av_unetI/netI 0.025 _diffrn_reflns_number 23999 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 1.26 _diffrn_reflns_theta_max 26.45 _diffrn_reflns_theta_full 26.45 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 2863 _reflns_number_gt 2355 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APPEX2 (BRUKER AXS, 2005)' _computing_cell_refinement 'APPEX2 (BRUKER AXS, 2005)' _computing_data_reduction 'APPEX2 (BRUKER AXS, 2005)' _computing_structure_solution 'SIR-97 (Giacovazzo et all, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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^)+(0.0634P)^2^+0.7995P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2863 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0582 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.128 _refine_ls_wR_factor_gt 0.109 _refine_ls_goodness_of_fit_ref 1.182 _refine_ls_restrained_S_all 1.182 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.296 _refine_diff_density_min -0.285 _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 N1 N 0.83037(16) 0.16662(11) 0.18817(4) 0.0181(3) Uani 1 1 d . . . C2 C 0.7332(2) 0.27626(14) 0.18126(5) 0.0225(4) Uani 1 1 d . . . H2A H 0.6093 0.2591 0.1771 0.027 Uiso 1 1 calc R . . H2B H 0.7777 0.321 0.157 0.027 Uiso 1 1 calc R . . C3 C 0.7633(2) 0.34547(14) 0.22135(5) 0.0224(4) Uani 1 1 d . . . H3A H 0.8268 0.4209 0.2158 0.027 Uiso 1 1 calc R . . H3B H 0.6523 0.3655 0.2348 0.027 Uiso 1 1 calc R . . O4 O 0.86406(15) 0.26651(10) 0.24748(3) 0.0260(3) Uani 1 1 d . . . C5 C 0.9077(2) 0.16606(14) 0.22634(5) 0.0215(3) Uani 1 1 d . . . O6 O 1.00171(16) 0.09030(11) 0.24049(3) 0.0300(3) Uani 1 1 d . . . C7 C 0.8839(2) 0.08379(14) 0.15790(5) 0.0186(3) Uani 1 1 d . . . H7 H 0.9883 0.0429 0.1639 0.022 Uiso 1 1 calc R . . C8 C 0.8105(2) 0.05401(14) 0.12204(4) 0.0179(3) Uani 1 1 d . . . C9 C 0.63541(19) 0.09328(14) 0.10557(4) 0.0180(3) Uani 1 1 d . . . H9 H 0.6052 0.1716 0.1189 0.022 Uiso 1 1 calc R . . C10 C 0.6370(2) 0.11162(14) 0.05891(5) 0.0217(4) Uani 1 1 d . . . C11 C 0.7703(2) 0.08078(16) 0.03543(5) 0.0271(4) Uani 1 1 d . . . H11 H 0.7644 0.0989 0.0067 0.033 Uiso 1 1 calc R . . C12 C 0.9296(2) 0.01933(17) 0.05112(5) 0.0288(4) Uani 1 1 d . . . H12A H 1.0254 0.0779 0.0523 0.035 Uiso 1 1 calc R . . H12B H 0.9628 -0.0453 0.0316 0.035 Uiso 1 1 calc R . . C13 C 0.9011(2) -0.03423(15) 0.09416(5) 0.0229(4) Uani 1 1 d . . . H13A H 0.8311 -0.1082 0.0918 0.027 Uiso 1 1 calc R . . H13B H 1.0136 -0.0562 0.1065 0.027 Uiso 1 1 calc R . . C14 C 0.4768(2) 0.16704(16) 0.04092(5) 0.0288(4) Uani 1 1 d . . . H14A H 0.4932 0.1805 0.0112 0.043 Uiso 1 1 calc R . . H14B H 0.4539 0.2439 0.0547 0.043 Uiso 1 1 calc R . . H14C H 0.3789 0.1128 0.0452 0.043 Uiso 1 1 calc R . . C15 C 0.5028(2) 0.00005(14) 0.11938(5) 0.0191(3) Uani 1 1 d . . . C16 C 0.4254(2) 0.01135(15) 0.15816(5) 0.0229(4) Uani 1 1 d . . . H16 H 0.4478 0.0806 0.1745 0.027 Uiso 1 1 calc R . . C17 C 0.3163(2) -0.07663(17) 0.17320(6) 0.0331(4) Uani 1 1 d . . . H17 H 0.262 -0.0664 0.1994 0.04 Uiso 1 1 calc R . . C18 C 0.2862(2) -0.17893(18) 0.15036(7) 0.0394(5) Uani 1 1 d . . . H18 H 0.2147 -0.2407 0.1612 0.047 Uiso 1 1 calc R . . C19 C 0.3601(2) -0.19139(16) 0.11174(7) 0.0380(5) Uani 1 1 d . . . H19 H 0.3384 -0.2616 0.0958 0.046 Uiso 1 1 calc R . . C20 C 0.4665(2) -0.10172(15) 0.09590(6) 0.0280(4) Uani 1 1 d . . . H20 H 0.5145 -0.1101 0.069 0.034 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 N1 0.0173(6) 0.0195(6) 0.0176(6) 0.0008(5) -0.0008(5) 0.0009(5) C2 0.0253(8) 0.0192(8) 0.0230(8) -0.0010(6) -0.0037(7) 0.0018(6) C3 0.0214(8) 0.0240(8) 0.0217(7) -0.0019(6) -0.0003(6) -0.0001(7) O4 0.0327(7) 0.0247(6) 0.0207(6) -0.0025(5) -0.0067(5) -0.0004(5) C5 0.0221(8) 0.0227(8) 0.0199(7) 0.0006(6) -0.0023(6) -0.0035(7) O6 0.0346(7) 0.0298(6) 0.0257(6) 0.0032(5) -0.0104(5) 0.0039(5) C7 0.0147(7) 0.0200(7) 0.0210(7) 0.0025(6) 0.0020(6) 0.0012(6) C8 0.0170(7) 0.0185(7) 0.0182(7) 0.0029(6) 0.0022(6) 0.0005(6) C9 0.0186(8) 0.0195(7) 0.0159(7) -0.0010(6) 0.0005(6) 0.0008(6) C10 0.0252(8) 0.0228(8) 0.0170(7) 0.0010(6) -0.0012(6) 0.0005(6) C11 0.0316(9) 0.0326(9) 0.0172(7) 0.0028(6) 0.0028(7) 0.0017(7) C12 0.0272(9) 0.0372(10) 0.0221(8) 0.0020(7) 0.0079(7) 0.0061(8) C13 0.0211(8) 0.0266(8) 0.0210(8) 0.0004(6) 0.0026(6) 0.0061(7) C14 0.0304(9) 0.0355(10) 0.0204(8) 0.0005(7) -0.0030(7) 0.0058(8) C15 0.0147(7) 0.0202(7) 0.0224(7) 0.0024(6) -0.0026(6) 0.0022(6) C16 0.0176(8) 0.0277(8) 0.0235(8) 0.0059(6) 0.0000(6) 0.0042(6) C17 0.0174(8) 0.0434(11) 0.0385(10) 0.0207(8) 0.0004(7) 0.0029(8) C18 0.0174(9) 0.0345(10) 0.0664(14) 0.0231(10) -0.0066(9) -0.0046(8) C19 0.0235(9) 0.0227(9) 0.0679(14) -0.0014(9) -0.0147(9) -0.0008(7) C20 0.0211(9) 0.0261(9) 0.0369(9) -0.0054(7) -0.0036(7) 0.0009(7) #----------------------------------------------------------------------------# # 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 N1 C5 1.370(2) . ? N1 C7 1.4062(19) . ? N1 C2 1.452(2) . ? C2 C3 1.523(2) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 O4 1.4474(19) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? O4 C5 1.3532(19) . ? C5 O6 1.2051(19) . ? C7 C8 1.332(2) . ? C7 H7 0.95 . ? C8 C13 1.506(2) . ? C8 C9 1.523(2) . ? C9 C10 1.519(2) . ? C9 C15 1.528(2) . ? C9 H9 1 . ? C10 C11 1.327(2) . ? C10 C14 1.505(2) . ? C11 C12 1.502(2) . ? C11 H11 0.95 . ? C12 C13 1.527(2) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? C15 C20 1.392(2) . ? C15 C16 1.394(2) . ? C16 C17 1.383(2) . ? C16 H16 0.95 . ? C17 C18 1.377(3) . ? C17 H17 0.95 . ? C18 C19 1.379(3) . ? C18 H18 0.95 . ? C19 C20 1.393(3) . ? C19 H19 0.95 . ? C20 H20 0.95 . ? 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 C5 N1 C7 119.46(13) . . ? C5 N1 C2 111.68(12) . . ? C7 N1 C2 126.74(12) . . ? N1 C2 C3 102.42(12) . . ? N1 C2 H2A 111.3 . . ? C3 C2 H2A 111.3 . . ? N1 C2 H2B 111.3 . . ? C3 C2 H2B 111.3 . . ? H2A C2 H2B 109.2 . . ? O4 C3 C2 105.67(12) . . ? O4 C3 H3A 110.6 . . ? C2 C3 H3A 110.6 . . ? O4 C3 H3B 110.6 . . ? C2 C3 H3B 110.6 . . ? H3A C3 H3B 108.7 . . ? C5 O4 C3 110.11(12) . . ? O6 C5 O4 122.64(14) . . ? O6 C5 N1 127.52(15) . . ? O4 C5 N1 109.84(13) . . ? C8 C7 N1 129.80(14) . . ? C8 C7 H7 115.1 . . ? N1 C7 H7 115.1 . . ? C7 C8 C13 118.76(14) . . ? C7 C8 C9 127.85(14) . . ? C13 C8 C9 113.31(13) . . ? C10 C9 C8 112.15(12) . . ? C10 C9 C15 112.68(12) . . ? C8 C9 C15 107.71(12) . . ? C10 C9 H9 108 . . ? C8 C9 H9 108 . . ? C15 C9 H9 108 . . ? C11 C10 C14 122.02(14) . . ? C11 C10 C9 122.47(14) . . ? C14 C10 C9 115.51(13) . . ? C10 C11 C12 124.60(14) . . ? C10 C11 H11 117.7 . . ? C12 C11 H11 117.7 . . ? C11 C12 C13 111.39(14) . . ? C11 C12 H12A 109.4 . . ? C13 C12 H12A 109.3 . . ? C11 C12 H12B 109.3 . . ? C13 C12 H12B 109.4 . . ? H12A C12 H12B 108 . . ? C8 C13 C12 110.85(14) . . ? C8 C13 H13A 109.5 . . ? C12 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C20 C15 C16 118.34(15) . . ? C20 C15 C9 122.06(14) . . ? C16 C15 C9 119.40(14) . . ? C17 C16 C15 121.01(17) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C18 C17 C16 120.16(18) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C19 119.75(17) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C18 C19 C20 120.43(18) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C15 C20 C19 120.25(17) . . ? C15 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C2 C3 0.45(17) . . . . ? C7 N1 C2 C3 -162.73(14) . . . . ? N1 C2 C3 O4 -3.30(16) . . . . ? C2 C3 O4 C5 5.24(17) . . . . ? C3 O4 C5 O6 174.74(15) . . . . ? C3 O4 C5 N1 -5.12(17) . . . . ? C7 N1 C5 O6 -12.4(2) . . . . ? C2 N1 C5 O6 -177.00(16) . . . . ? C7 N1 C5 O4 167.41(13) . . . . ? C2 N1 C5 O4 2.85(18) . . . . ? C5 N1 C7 C8 167.30(15) . . . . ? C2 N1 C7 C8 -30.7(3) . . . . ? N1 C7 C8 C13 176.98(15) . . . . ? N1 C7 C8 C9 -6.7(3) . . . . ? C7 C8 C9 C10 144.12(16) . . . . ? C13 C8 C9 C10 -39.44(18) . . . . ? C7 C8 C9 C15 -91.35(19) . . . . ? C13 C8 C9 C15 85.10(15) . . . . ? C8 C9 C10 C11 8.4(2) . . . . ? C15 C9 C10 C11 -113.35(17) . . . . ? C8 C9 C10 C14 -171.73(13) . . . . ? C15 C9 C10 C14 66.53(18) . . . . ? C14 C10 C11 C12 -176.62(16) . . . . ? C9 C10 C11 C12 3.3(3) . . . . ? C10 C11 C12 C13 15.7(2) . . . . ? C7 C8 C13 C12 -124.09(16) . . . . ? C9 C8 C13 C12 59.11(18) . . . . ? C11 C12 C13 C8 -45.4(2) . . . . ? C10 C9 C15 C20 36.0(2) . . . . ? C8 C9 C15 C20 -88.25(17) . . . . ? C10 C9 C15 C16 -149.34(14) . . . . ? C8 C9 C15 C16 86.44(17) . . . . ? C20 C15 C16 C17 0.6(2) . . . . ? C9 C15 C16 C17 -174.33(14) . . . . ? C15 C16 C17 C18 1.8(2) . . . . ? C16 C17 C18 C19 -2.4(3) . . . . ? C17 C18 C19 C20 0.7(3) . . . . ? C16 C15 C20 C19 -2.3(2) . . . . ? C9 C15 C20 C19 172.48(15) . . . . ? C18 C19 C20 C15 1.7(3) . . . . ? # END of CIF # Attachment '- ccdc_deposit 3fi.cif' data_lm11hff1n _database_code_depnum_ccdc_archive 'CCDC 804848' #TrackingRef '- ccdc_deposit 3fi.cif' _audit_creation_date 2010-09-01T16:44:31-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H21 N O2' _chemical_formula_sum 'C18 H21 N O2' _chemical_formula_weight 283.36 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration rm #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'P c a 21' _space_group_name_Hall 'P 2c -2ac' _space_group_IT_number 29 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 11.930(2) _cell_length_b 8.5702(15) _cell_length_c 30.278(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3095.6(9) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 507 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 19.11 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_absorpt_correction_T_min 0.8485 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromador graphite _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'BRUKER APPEX-II CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_reflns_av_R_equivalents 0.1298 _diffrn_reflns_av_unetI/netI 0.0989 _diffrn_reflns_number 15206 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 20.82 _diffrn_reflns_theta_full 20.82 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 1666 _reflns_number_gt 1155 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APPEX2 (BRUKER AXS, 2005)' _computing_cell_refinement 'APPEX2 (BRUKER AXS, 2005)' _computing_data_reduction 'APPEX2 (BRUKER AXS, 2005)' _computing_structure_solution 'SIR2004 (Giacovazzo et al, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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^)+(0.1019P)^2^+2.2043P] 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 0.0016(7) _refine_ls_number_reflns 1666 _refine_ls_number_parameters 396 _refine_ls_number_restraints 387 _refine_ls_R_factor_all 0.1036 _refine_ls_R_factor_gt 0.0644 _refine_ls_wR_factor_ref 0.1788 _refine_ls_wR_factor_gt 0.1515 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 0.915 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.371 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.068 #----------------------------------------------------------------------------# # 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 '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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0 '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 N1 N -0.0782(6) 0.5883(10) 0.8937(3) 0.0193(7) Uani 1 1 d U . . C2 C -0.1111(8) 0.4483(11) 0.8772(3) 0.0191(8) Uani 1 1 d U . . O3 O -0.0227(5) 0.3514(8) 0.8733(2) 0.0194(8) Uani 1 1 d U . . C4 C 0.0772(8) 0.4319(11) 0.8904(3) 0.0198(8) Uani 1 1 d U . . H4A H 0.1426 0.4149 0.8708 0.024 Uiso 1 1 calc R . . H4B H 0.0959 0.3956 0.9205 0.024 Uiso 1 1 calc R . . C5 C 0.0427(7) 0.6000(12) 0.8906(3) 0.0198(8) Uani 1 1 d U . . H5A H 0.0746 0.6561 0.9162 0.024 Uiso 1 1 calc R . . H5B H 0.0658 0.6534 0.863 0.024 Uiso 1 1 calc R . . O6 O -0.2051(5) 0.4087(7) 0.86654(19) 0.0191(9) Uani 1 1 d U . . C7 C -0.1499(8) 0.7223(12) 0.8902(4) 0.0195(7) Uani 1 1 d U . . H7 H -0.169(7) 0.744(10) 0.861(3) 0.023 Uiso 1 1 d . . . C8 C -0.1755(8) 0.8140(12) 0.9237(3) 0.0200(7) Uani 1 1 d U . . C9 C -0.2526(8) 0.9521(11) 0.9201(3) 0.0205(8) Uani 1 1 d U . . H9 H -0.3149 0.9365 0.9417 0.025 Uiso 1 1 calc R . . C10 C -0.1871(8) 1.0959(12) 0.9345(3) 0.0208(8) Uani 1 1 d U . . H10A H -0.1338 1.1252 0.9108 0.025 Uiso 1 1 calc R . . H10B H -0.2398 1.184 0.9386 0.025 Uiso 1 1 calc R . . C11 C -0.1235(8) 1.0696(13) 0.9766(3) 0.0208(8) Uani 1 1 d U . . H11 H -0.084(7) 1.176(11) 0.982(3) 0.025 Uiso 1 1 d . . . C12 C -0.0980(8) 0.9307(12) 0.9931(3) 0.0207(8) Uani 1 1 d U . . C13 C -0.1328(8) 0.7796(12) 0.9704(3) 0.0204(7) Uani 1 1 d U . . H13 H -0.0642 0.7133 0.9675 0.024 Uiso 1 1 calc R . . C14 C -0.2192(8) 0.6857(12) 0.9964(3) 0.0208(8) Uani 1 1 d U . . C15 C -0.2145(8) 0.5248(11) 0.9960(3) 0.0211(8) Uani 1 1 d U . . H15 H -0.1557 0.4745 0.9803 0.025 Uiso 1 1 calc R . . C16 C -0.2936(8) 0.4346(12) 1.0178(3) 0.0216(9) Uani 1 1 d U . . H16 H -0.2892 0.3239 1.0167 0.026 Uiso 1 1 calc R . . C17 C -0.3788(8) 0.5064(12) 1.0412(3) 0.0218(9) Uani 1 1 d U . . H17 H -0.4335 0.446 1.0563 0.026 Uiso 1 1 calc R . . C18 C -0.3827(8) 0.6657(12) 1.0422(3) 0.0216(9) Uani 1 1 d U . . H18 H -0.4404 0.7156 1.0586 0.026 Uiso 1 1 calc R . . C19 C -0.3045(8) 0.7568(12) 1.0199(3) 0.0212(8) Uani 1 1 d U . . H19 H -0.3097 0.8674 1.0208 0.025 Uiso 1 1 calc R . . C20 C -0.0290(8) 0.9093(11) 1.0342(3) 0.0211(9) Uani 1 1 d U . . H20A H 0.0449 0.8679 1.0263 0.032 Uiso 1 1 calc R . . H20B H -0.067 0.836 1.054 0.032 Uiso 1 1 calc R . . H20C H -0.0201 1.0101 1.0491 0.032 Uiso 1 1 calc R . . C21 C -0.3054(7) 0.9780(12) 0.8748(3) 0.0210(9) Uani 1 1 d U . . H21A H -0.2464 1.0001 0.8531 0.031 Uiso 1 1 calc R . . H21B H -0.3573 1.0665 0.8762 0.031 Uiso 1 1 calc R . . H21C H -0.3464 0.884 0.8659 0.031 Uiso 1 1 calc R . . N31 N -0.2118(6) 0.4135(10) 0.7607(2) 0.0184(7) Uani 1 1 d U . . C32 C -0.1753(8) 0.5521(12) 0.7782(3) 0.0183(8) Uani 1 1 d U . . O33 O -0.2643(5) 0.6512(8) 0.7820(2) 0.0183(8) Uani 1 1 d U . . C34 C -0.3639(7) 0.5759(11) 0.7650(3) 0.0187(8) Uani 1 1 d U . . H34A H -0.3822 0.6146 0.735 0.022 Uiso 1 1 calc R . . H34B H -0.4289 0.5941 0.7846 0.022 Uiso 1 1 calc R . . C35 C -0.3317(7) 0.4006(12) 0.7638(3) 0.0187(8) Uani 1 1 d U . . H35A H -0.3551 0.3459 0.7911 0.022 Uiso 1 1 calc R . . H35B H -0.364 0.3469 0.7378 0.022 Uiso 1 1 calc R . . O36 O -0.0812(5) 0.5885(7) 0.7884(2) 0.0185(9) Uani 1 1 d U . . C37 C -0.1425(8) 0.2780(12) 0.7665(3) 0.0187(7) Uani 1 1 d U . . H37 H -0.121(7) 0.270(10) 0.797(3) 0.022 Uiso 1 1 d . . . C38 C -0.1118(8) 0.1913(12) 0.7330(3) 0.0193(7) Uani 1 1 d U . . C39 C -0.0381(8) 0.0466(11) 0.7383(3) 0.0201(8) Uani 1 1 d U . . H39 H 0.0301 0.0627 0.7196 0.024 Uiso 1 1 calc R . . C40 C -0.1004(8) -0.0951(12) 0.7198(3) 0.0204(8) Uani 1 1 d U . . H40A H -0.0477 -0.1839 0.7171 0.024 Uiso 1 1 calc R . . H40B H -0.1607 -0.1257 0.7405 0.024 Uiso 1 1 calc R . . C41 C -0.1503(8) -0.0609(12) 0.6754(3) 0.0205(8) Uani 1 1 d U . . H41 H -0.176(7) -0.142(11) 0.655(3) 0.025 Uiso 1 1 d . . . C42 C -0.1684(8) 0.0769(12) 0.6592(3) 0.0201(8) Uani 1 1 d U . . C43 C -0.1423(8) 0.2260(12) 0.6847(3) 0.0197(7) Uani 1 1 d U . . H43 H -0.212 0.2909 0.6849 0.024 Uiso 1 1 calc R . . C44 C -0.0500(8) 0.3238(12) 0.6638(3) 0.0201(8) Uani 1 1 d U . . C45 C 0.0428(8) 0.2570(12) 0.6433(3) 0.0205(8) Uani 1 1 d U . . H45 H 0.0479 0.1465 0.6414 0.025 Uiso 1 1 calc R . . C46 C 0.1286(8) 0.3478(12) 0.6254(3) 0.0208(9) Uani 1 1 d U . . H46 H 0.191 0.2986 0.6118 0.025 Uiso 1 1 calc R . . C47 C 0.1235(8) 0.5069(12) 0.6272(3) 0.0209(9) Uani 1 1 d U . . H47 H 0.1821 0.568 0.6149 0.025 Uiso 1 1 calc R . . C48 C 0.0318(8) 0.5790(13) 0.6472(3) 0.0207(9) Uani 1 1 d U . . H48 H 0.0278 0.6896 0.6488 0.025 Uiso 1 1 calc R . . C49 C -0.0542(8) 0.4869(12) 0.6649(3) 0.0203(8) Uani 1 1 d U . . H49 H -0.1172 0.5366 0.6779 0.024 Uiso 1 1 calc R . . C50 C -0.2224(8) 0.1040(12) 0.6145(3) 0.0205(9) Uani 1 1 d U . . H50A H -0.226 0.0051 0.5983 0.031 Uiso 1 1 calc R . . H50B H -0.1778 0.1794 0.5977 0.031 Uiso 1 1 calc R . . H50C H -0.2984 0.1449 0.6186 0.031 Uiso 1 1 calc R . . C51 C 0.0023(8) 0.0163(12) 0.7859(3) 0.0205(9) Uani 1 1 d U . . H51A H 0.0375 0.1109 0.7976 0.031 Uiso 1 1 calc R . . H51B H 0.057 -0.0691 0.7859 0.031 Uiso 1 1 calc R . . H51C H -0.0618 -0.0123 0.8044 0.031 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 N1 0.0174(12) 0.0163(15) 0.0242(15) -0.0010(13) -0.0014(13) -0.0010(12) C2 0.0168(13) 0.0161(15) 0.0244(16) -0.0005(14) -0.0011(14) -0.0010(12) O3 0.0166(13) 0.0162(16) 0.0255(16) -0.0003(14) -0.0008(14) -0.0010(13) C4 0.0171(13) 0.0167(17) 0.0256(17) -0.0006(15) -0.0010(15) -0.0014(13) C5 0.0173(13) 0.0168(16) 0.0252(16) -0.0011(15) -0.0012(14) -0.0014(13) O6 0.0167(14) 0.0163(17) 0.0244(18) -0.0002(16) -0.0011(15) -0.0014(14) C7 0.0190(13) 0.0164(15) 0.0232(14) -0.0008(13) -0.0020(13) -0.0003(12) C8 0.0206(13) 0.0168(14) 0.0226(14) -0.0006(12) -0.0021(12) 0.0006(11) C9 0.0216(14) 0.0171(15) 0.0228(16) -0.0008(13) -0.0027(13) 0.0011(12) C10 0.0223(15) 0.0172(15) 0.0230(16) -0.0007(14) -0.0030(13) 0.0010(13) C11 0.0224(15) 0.0172(15) 0.0228(16) -0.0007(14) -0.0030(13) 0.0005(13) C12 0.0222(15) 0.0173(15) 0.0226(15) -0.0006(13) -0.0027(13) 0.0005(13) C13 0.0215(13) 0.0171(15) 0.0225(14) -0.0005(12) -0.0022(12) 0.0007(12) C14 0.0222(15) 0.0173(15) 0.0227(15) -0.0005(13) -0.0015(12) 0.0006(13) C15 0.0228(16) 0.0174(16) 0.0231(17) -0.0003(15) -0.0013(14) 0.0006(14) C16 0.0233(17) 0.0176(17) 0.0239(18) -0.0001(16) -0.0010(15) 0.0003(14) C17 0.0233(17) 0.0181(17) 0.0241(18) -0.0002(16) -0.0008(14) 0.0002(15) C18 0.0229(17) 0.0181(17) 0.0239(18) -0.0004(16) -0.0007(14) 0.0004(15) C19 0.0226(16) 0.0176(17) 0.0232(17) -0.0005(15) -0.0011(13) 0.0006(14) C20 0.0229(17) 0.0176(18) 0.0228(17) -0.0004(15) -0.0029(14) 0.0004(15) C21 0.0223(17) 0.0175(18) 0.0231(17) -0.0009(15) -0.0029(14) 0.0015(14) N31 0.0166(13) 0.0187(15) 0.0200(14) -0.0009(13) -0.0029(13) -0.0019(12) C32 0.0159(13) 0.0185(16) 0.0205(15) -0.0008(14) -0.0029(13) -0.0017(13) O33 0.0155(13) 0.0185(16) 0.0209(16) -0.0006(14) -0.0028(14) -0.0020(13) C34 0.0159(13) 0.0190(17) 0.0211(16) -0.0009(15) -0.0029(14) -0.0023(13) C35 0.0165(13) 0.0190(16) 0.0207(16) -0.0011(15) -0.0028(14) -0.0023(13) O36 0.0159(14) 0.0186(18) 0.0210(17) -0.0007(16) -0.0030(15) -0.0015(14) C37 0.0183(13) 0.0186(15) 0.0191(14) -0.0005(13) -0.0033(12) -0.0013(12) C38 0.0205(13) 0.0188(15) 0.0187(13) -0.0003(12) -0.0035(11) -0.0004(12) C39 0.0221(14) 0.0191(16) 0.0190(15) -0.0003(13) -0.0038(12) 0.0004(12) C40 0.0229(15) 0.0190(15) 0.0193(15) -0.0004(14) -0.0040(13) 0.0006(13) C41 0.0229(15) 0.0193(15) 0.0193(15) -0.0005(14) -0.0041(13) 0.0004(14) C42 0.0222(14) 0.0193(16) 0.0189(14) -0.0006(13) -0.0043(13) 0.0003(13) C43 0.0213(13) 0.0192(15) 0.0187(13) -0.0003(12) -0.0039(11) -0.0001(12) C44 0.0217(14) 0.0200(16) 0.0187(14) 0.0002(13) -0.0037(12) -0.0003(13) C45 0.0219(16) 0.0205(17) 0.0189(16) 0.0004(15) -0.0034(13) -0.0003(14) C46 0.0220(16) 0.0211(18) 0.0193(17) 0.0005(16) -0.0032(14) -0.0004(15) C47 0.0223(17) 0.0210(18) 0.0193(17) 0.0007(16) -0.0033(14) -0.0007(15) C48 0.0224(17) 0.0205(17) 0.0192(17) 0.0005(15) -0.0035(15) -0.0007(14) C49 0.0220(16) 0.0201(16) 0.0189(16) 0.0006(15) -0.0037(14) -0.0003(14) C50 0.0227(17) 0.0197(18) 0.0190(16) -0.0010(15) -0.0046(15) 0.0004(16) C51 0.0230(17) 0.0195(18) 0.0191(16) -0.0002(15) -0.0039(14) 0.0007(15) #----------------------------------------------------------------------------# # 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 N1 C2 1.357(12) . ? N1 C7 1.436(13) . ? N1 C5 1.449(11) . ? C2 O6 1.216(10) . ? C2 O3 1.348(11) . ? O3 C4 1.470(11) . ? C4 C5 1.499(13) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C7 C8 1.320(13) . ? C7 H7 0.94(9) . ? C8 C9 1.503(13) . ? C8 C13 1.531(14) . ? C9 C10 1.524(13) . ? C9 C21 1.526(13) . ? C9 H9 1 . ? C10 C11 1.500(14) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.326(14) . ? C11 H11 1.04(9) . ? C12 C20 1.504(13) . ? C12 C13 1.523(14) . ? C13 C14 1.526(14) . ? C13 H13 1 . ? C14 C15 1.380(13) . ? C14 C19 1.384(13) . ? C15 C16 1.387(13) . ? C15 H15 0.95 . ? C16 C17 1.383(13) . ? C16 H16 0.95 . ? C17 C18 1.367(13) . ? C17 H17 0.95 . ? C18 C19 1.392(13) . ? C18 H18 0.95 . ? C19 H19 0.95 . ? C20 H20A 0.98 . ? C20 H20B 0.98 . ? C20 H20C 0.98 . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? N31 C32 1.371(12) . ? N31 C37 1.437(12) . ? N31 C35 1.438(11) . ? C32 O36 1.205(10) . ? C32 O33 1.365(11) . ? O33 C34 1.447(11) . ? C34 C35 1.551(13) . ? C34 H34A 0.99 . ? C34 H34B 0.99 . ? C35 H35A 0.99 . ? C35 H35B 0.99 . ? C37 C38 1.310(13) . ? C37 H37 0.95(9) . ? C38 C39 1.529(13) . ? C38 C43 1.536(13) . ? C39 C40 1.530(13) . ? C39 C51 1.543(13) . ? C39 H39 1 . ? C40 C41 1.497(14) . ? C40 H40A 0.99 . ? C40 H40B 0.99 . ? C41 C42 1.297(13) . ? C41 H41 0.98(9) . ? C42 C50 1.518(13) . ? C42 C43 1.525(13) . ? C43 C44 1.522(13) . ? C43 H43 1 . ? C44 C45 1.393(13) . ? C44 C49 1.399(13) . ? C45 C46 1.395(13) . ? C45 H45 0.95 . ? C46 C47 1.365(13) . ? C46 H46 0.95 . ? C47 C48 1.394(13) . ? C47 H47 0.95 . ? C48 C49 1.401(13) . ? C48 H48 0.95 . ? C49 H49 0.95 . ? C50 H50A 0.98 . ? C50 H50B 0.98 . ? C50 H50C 0.98 . ? C51 H51A 0.98 . ? C51 H51B 0.98 . ? C51 H51C 0.98 . ? 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 N1 C7 120.5(8) . . ? C2 N1 C5 109.0(8) . . ? C7 N1 C5 122.2(8) . . ? O6 C2 O3 121.7(9) . . ? O6 C2 N1 127.7(9) . . ? O3 C2 N1 110.6(8) . . ? C2 O3 C4 108.3(7) . . ? O3 C4 C5 103.3(8) . . ? O3 C4 H4A 111.1 . . ? C5 C4 H4A 111.1 . . ? O3 C4 H4B 111.1 . . ? C5 C4 H4B 111.1 . . ? H4A C4 H4B 109.1 . . ? N1 C5 C4 101.9(8) . . ? N1 C5 H5A 111.4 . . ? C4 C5 H5A 111.4 . . ? N1 C5 H5B 111.4 . . ? C4 C5 H5B 111.4 . . ? H5A C5 H5B 109.2 . . ? C8 C7 N1 123.8(10) . . ? C8 C7 H7 124(5) . . ? N1 C7 H7 112(5) . . ? C7 C8 C9 123.6(9) . . ? C7 C8 C13 121.2(9) . . ? C9 C8 C13 115.0(8) . . ? C8 C9 C10 107.6(8) . . ? C8 C9 C21 115.7(8) . . ? C10 C9 C21 110.5(8) . . ? C8 C9 H9 107.6 . . ? C10 C9 H9 107.6 . . ? C21 C9 H9 107.6 . . ? C11 C10 C9 112.4(9) . . ? C11 C10 H10A 109.1 . . ? C9 C10 H10A 109.1 . . ? C11 C10 H10B 109.1 . . ? C9 C10 H10B 109.1 . . ? H10A C10 H10B 107.9 . . ? C12 C11 C10 124.8(10) . . ? C12 C11 H11 128(5) . . ? C10 C11 H11 104(5) . . ? C11 C12 C20 123.1(9) . . ? C11 C12 C13 122.1(9) . . ? C20 C12 C13 114.7(8) . . ? C12 C13 C14 113.6(8) . . ? C12 C13 C8 110.0(8) . . ? C14 C13 C8 110.6(8) . . ? C12 C13 H13 107.4 . . ? C14 C13 H13 107.4 . . ? C8 C13 H13 107.4 . . ? C15 C14 C19 118.3(10) . . ? C15 C14 C13 119.7(9) . . ? C19 C14 C13 122.0(9) . . ? C14 C15 C16 121.7(10) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C17 C16 C15 119.7(10) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C18 C17 C16 118.8(9) . . ? C18 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? C17 C18 C19 121.8(9) . . ? C17 C18 H18 119.1 . . ? C19 C18 H18 119.1 . . ? C14 C19 C18 119.7(10) . . ? C14 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? 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 . . ? C9 C21 H21A 109.5 . . ? C9 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C9 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C32 N31 C37 118.0(8) . . ? C32 N31 C35 111.0(8) . . ? C37 N31 C35 120.2(8) . . ? O36 C32 O33 122.8(9) . . ? O36 C32 N31 128.2(9) . . ? O33 C32 N31 108.9(8) . . ? C32 O33 C34 109.4(7) . . ? O33 C34 C35 103.7(7) . . ? O33 C34 H34A 111 . . ? C35 C34 H34A 111 . . ? O33 C34 H34B 111 . . ? C35 C34 H34B 111 . . ? H34A C34 H34B 109 . . ? N31 C35 C34 100.0(7) . . ? N31 C35 H35A 111.8 . . ? C34 C35 H35A 111.8 . . ? N31 C35 H35B 111.8 . . ? C34 C35 H35B 111.8 . . ? H35A C35 H35B 109.5 . . ? C38 C37 N31 121.6(9) . . ? C38 C37 H37 129(5) . . ? N31 C37 H37 109(5) . . ? C37 C38 C39 122.7(9) . . ? C37 C38 C43 124.2(9) . . ? C39 C38 C43 113.1(8) . . ? C38 C39 C40 109.0(8) . . ? C38 C39 C51 114.5(8) . . ? C40 C39 C51 111.1(8) . . ? C38 C39 H39 107.3 . . ? C40 C39 H39 107.3 . . ? C51 C39 H39 107.3 . . ? C41 C40 C39 111.5(8) . . ? C41 C40 H40A 109.3 . . ? C39 C40 H40A 109.3 . . ? C41 C40 H40B 109.3 . . ? C39 C40 H40B 109.3 . . ? H40A C40 H40B 108 . . ? C42 C41 C40 125.7(10) . . ? C42 C41 H41 111(5) . . ? C40 C41 H41 123(5) . . ? C41 C42 C50 123.2(9) . . ? C41 C42 C43 122.5(9) . . ? C50 C42 C43 114.2(8) . . ? C44 C43 C42 113.5(8) . . ? C44 C43 C38 109.4(8) . . ? C42 C43 C38 111.6(8) . . ? C44 C43 H43 107.4 . . ? C42 C43 H43 107.4 . . ? C38 C43 H43 107.4 . . ? C45 C44 C49 116.7(9) . . ? C45 C44 C43 122.3(10) . . ? C49 C44 C43 120.9(9) . . ? C44 C45 C46 121.8(10) . . ? C44 C45 H45 119.1 . . ? C46 C45 H45 119.1 . . ? C47 C46 C45 120.6(10) . . ? C47 C46 H46 119.7 . . ? C45 C46 H46 119.7 . . ? C46 C47 C48 119.7(10) . . ? C46 C47 H47 120.2 . . ? C48 C47 H47 120.2 . . ? C47 C48 C49 119.4(10) . . ? C47 C48 H48 120.3 . . ? C49 C48 H48 120.3 . . ? C44 C49 C48 121.8(10) . . ? C44 C49 H49 119.1 . . ? C48 C49 H49 119.1 . . ? C42 C50 H50A 109.5 . . ? C42 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C42 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C39 C51 H51A 109.5 . . ? C39 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C39 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 N1 C2 O6 -15.8(16) . . . . ? C5 N1 C2 O6 -164.6(10) . . . . ? C7 N1 C2 O3 163.6(8) . . . . ? C5 N1 C2 O3 14.8(11) . . . . ? O6 C2 O3 C4 -178.0(9) . . . . ? N1 C2 O3 C4 2.5(11) . . . . ? C2 O3 C4 C5 -17.8(10) . . . . ? C2 N1 C5 C4 -24.9(11) . . . . ? C7 N1 C5 C4 -173.1(8) . . . . ? O3 C4 C5 N1 24.9(10) . . . . ? C2 N1 C7 C8 129.9(11) . . . . ? C5 N1 C7 C8 -85.4(14) . . . . ? N1 C7 C8 C9 -178.6(9) . . . . ? N1 C7 C8 C13 -2.2(16) . . . . ? C7 C8 C9 C10 -121.5(11) . . . . ? C13 C8 C9 C10 61.9(11) . . . . ? C7 C8 C9 C21 2.6(15) . . . . ? C13 C8 C9 C21 -174.0(8) . . . . ? C8 C9 C10 C11 -46.7(11) . . . . ? C21 C9 C10 C11 -173.8(8) . . . . ? C9 C10 C11 C12 19.0(14) . . . . ? C10 C11 C12 C20 176.8(9) . . . . ? C10 C11 C12 C13 -0.7(16) . . . . ? C11 C12 C13 C14 -112.6(11) . . . . ? C20 C12 C13 C14 69.6(11) . . . . ? C11 C12 C13 C8 12.0(13) . . . . ? C20 C12 C13 C8 -165.7(8) . . . . ? C7 C8 C13 C12 139.6(10) . . . . ? C9 C8 C13 C12 -43.8(11) . . . . ? C7 C8 C13 C14 -94.0(12) . . . . ? C9 C8 C13 C14 82.6(11) . . . . ? C12 C13 C14 C15 -144.0(9) . . . . ? C8 C13 C14 C15 91.6(11) . . . . ? C12 C13 C14 C19 37.3(13) . . . . ? C8 C13 C14 C19 -87.0(11) . . . . ? C19 C14 C15 C16 1.0(15) . . . . ? C13 C14 C15 C16 -177.7(9) . . . . ? C14 C15 C16 C17 -0.9(15) . . . . ? C15 C16 C17 C18 0.0(14) . . . . ? C16 C17 C18 C19 0.9(14) . . . . ? C15 C14 C19 C18 -0.1(14) . . . . ? C13 C14 C19 C18 178.5(9) . . . . ? C17 C18 C19 C14 -0.9(14) . . . . ? C37 N31 C32 O36 20.6(15) . . . . ? C35 N31 C32 O36 165.1(10) . . . . ? C37 N31 C32 O33 -160.8(8) . . . . ? C35 N31 C32 O33 -16.3(11) . . . . ? O36 C32 O33 C34 176.9(9) . . . . ? N31 C32 O33 C34 -1.8(10) . . . . ? C32 O33 C34 C35 17.3(10) . . . . ? C32 N31 C35 C34 25.4(10) . . . . ? C37 N31 C35 C34 169.0(8) . . . . ? O33 C34 C35 N31 -24.8(9) . . . . ? C32 N31 C37 C38 -127.2(10) . . . . ? C35 N31 C37 C38 91.7(12) . . . . ? N31 C37 C38 C39 180.0(9) . . . . ? N31 C37 C38 C43 2.0(16) . . . . ? C37 C38 C39 C40 122.0(10) . . . . ? C43 C38 C39 C40 -59.8(10) . . . . ? C37 C38 C39 C51 -3.1(14) . . . . ? C43 C38 C39 C51 175.1(8) . . . . ? C38 C39 C40 C41 47.0(11) . . . . ? C51 C39 C40 C41 174.0(8) . . . . ? C39 C40 C41 C42 -18.5(14) . . . . ? C40 C41 C42 C50 -178.2(9) . . . . ? C40 C41 C42 C43 -1.3(16) . . . . ? C41 C42 C43 C44 114.7(11) . . . . ? C50 C42 C43 C44 -68.1(11) . . . . ? C41 C42 C43 C38 -9.3(14) . . . . ? C50 C42 C43 C38 167.8(8) . . . . ? C37 C38 C43 C44 91.9(12) . . . . ? C39 C38 C43 C44 -86.2(10) . . . . ? C37 C38 C43 C42 -141.7(10) . . . . ? C39 C38 C43 C42 40.1(11) . . . . ? C42 C43 C44 C45 -36.7(12) . . . . ? C38 C43 C44 C45 88.5(11) . . . . ? C42 C43 C44 C49 144.0(9) . . . . ? C38 C43 C44 C49 -90.7(11) . . . . ? C49 C44 C45 C46 1.2(14) . . . . ? C43 C44 C45 C46 -178.1(9) . . . . ? C44 C45 C46 C47 -0.5(14) . . . . ? C45 C46 C47 C48 0.1(14) . . . . ? C46 C47 C48 C49 -0.5(14) . . . . ? C45 C44 C49 C48 -1.6(14) . . . . ? C43 C44 C49 C48 177.7(8) . . . . ? C47 C48 C49 C44 1.3(14) . . . . ? # END of CIF # Attachment '- ccdc_deposit 3gi.cif' data_lm14hff1n _database_code_depnum_ccdc_archive 'CCDC 804849' #TrackingRef '- ccdc_deposit 3gi.cif' _audit_creation_date 2010-10-17T21:46:34-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common FL008t17cris _chemical_formula_moiety 'C24 H25 N O2' _chemical_formula_sum 'C24 H25 N O2' _chemical_formula_weight 359.45 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _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 8.2299(2) _cell_length_b 9.6964(2) _cell_length_c 23.9162(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1908.52(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2490 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 21.86 _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 0.27 _exptl_crystal_size_min 0.26 _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9086 _exptl_absorpt_correction_T_max 0.9735 _exptl_absorpt_process_details 'BRUKER AXS - SADABS' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Bruker X8 kappa APEXII CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_reflns_av_R_equivalents 0.0616 _diffrn_reflns_av_unetI/netI 0.0519 _diffrn_reflns_number 16051 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.7 _diffrn_reflns_theta_max 28.28 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 2702 _reflns_number_gt 2165 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 v2010.9-1 (Bruker AXS, 2010)' _computing_cell_refinement 'APEX2 v2010.9-1 (Bruker AXS, 2010)' _computing_data_reduction 'APEX2 v2010.9-1 (Bruker AXS, 2010)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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^)+(0.0464P)^2^+0.1059P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2702 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.0979 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_restrained_S_all 1.04 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.198 _refine_diff_density_min -0.238 _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 O1 O 1.0962(2) 0.66046(15) 0.27307(6) 0.0218(4) Uani 1 1 d . . . C2 C 0.9688(3) 0.6554(2) 0.30841(9) 0.0183(5) Uani 1 1 d . . . N3 N 0.9535(2) 0.52518(17) 0.33055(7) 0.0162(4) Uani 1 1 d . . . C4 C 1.0975(3) 0.4409(2) 0.31768(9) 0.0169(5) Uani 1 1 d . . . H4 H 1.0617 0.3485 0.3037 0.02 Uiso 1 1 calc R . . C5 C 1.1685(3) 0.5243(2) 0.26903(9) 0.0200(5) Uani 1 1 d . . . H5A H 1.2883 0.5301 0.2722 0.024 Uiso 1 1 calc R . . H5B H 1.1408 0.4808 0.2328 0.024 Uiso 1 1 calc R . . O6 O 0.8814(2) 0.75338(15) 0.31677(6) 0.0235(4) Uani 1 1 d . . . C7 C 0.8453(3) 0.5079(2) 0.37602(9) 0.0169(5) Uani 1 1 d . . . H7 H 0.8141 0.59 0.3948 0.02 Uiso 1 1 calc R . . C8 C 0.7814(3) 0.3918(2) 0.39592(9) 0.0170(5) Uani 1 1 d . . . C9 C 0.8017(3) 0.2473(2) 0.37302(9) 0.0165(4) Uani 1 1 d . . . H9 H 0.8931 0.2485 0.3455 0.02 Uiso 1 1 calc R . . C10 C 0.8463(3) 0.1478(2) 0.41975(10) 0.0196(5) Uani 1 1 d . . . C11 C 0.8216(3) 0.1783(2) 0.47321(10) 0.0219(5) Uani 1 1 d . . . H11 H 0.8498 0.1104 0.5001 0.026 Uiso 1 1 calc R . . C12 C 0.7529(3) 0.3113(2) 0.49429(9) 0.0242(6) Uani 1 1 d . . . H12A H 0.8406 0.366 0.512 0.029 Uiso 1 1 calc R . . H12B H 0.6699 0.2917 0.5232 0.029 Uiso 1 1 calc R . . C13 C 0.6757(3) 0.3958(2) 0.44718(9) 0.0200(5) Uani 1 1 d . . . H13A H 0.5671 0.3579 0.4382 0.024 Uiso 1 1 calc R . . H13B H 0.6617 0.4926 0.4595 0.024 Uiso 1 1 calc R . . C14 C 0.6459(3) 0.2055(2) 0.34184(9) 0.0163(5) Uani 1 1 d . . . C15 C 0.5457(3) 0.0999(2) 0.35999(10) 0.0220(5) Uani 1 1 d . . . H15 H 0.5719 0.052 0.3934 0.026 Uiso 1 1 calc R . . C16 C 0.4077(3) 0.0628(2) 0.33025(11) 0.0275(6) Uani 1 1 d . . . H16 H 0.3409 -0.0103 0.3433 0.033 Uiso 1 1 calc R . . C17 C 0.3673(3) 0.1320(2) 0.28168(10) 0.0268(6) Uani 1 1 d . . . H17 H 0.2737 0.1059 0.261 0.032 Uiso 1 1 calc R . . C18 C 0.4644(3) 0.2399(2) 0.26323(10) 0.0250(6) Uani 1 1 d . . . H18 H 0.436 0.2894 0.2304 0.03 Uiso 1 1 calc R . . C19 C 0.6032(3) 0.2752(2) 0.29298(9) 0.0193(5) Uani 1 1 d . . . H19 H 0.6702 0.3481 0.2798 0.023 Uiso 1 1 calc R . . C20 C 0.9238(3) 0.0150(2) 0.40164(11) 0.0300(6) Uani 1 1 d . . . H20A H 0.9442 -0.0429 0.4345 0.045 Uiso 1 1 calc R . . H20B H 1.0269 0.0347 0.3828 0.045 Uiso 1 1 calc R . . H20C H 0.851 -0.0335 0.3759 0.045 Uiso 1 1 calc R . . C21 C 1.2089(3) 0.4213(2) 0.36830(9) 0.0181(5) Uani 1 1 d . . . H21A H 1.1483 0.3702 0.3975 0.022 Uiso 1 1 calc R . . H21B H 1.3022 0.3634 0.3569 0.022 Uiso 1 1 calc R . . C22 C 1.2733(3) 0.5531(2) 0.39362(9) 0.0179(5) Uani 1 1 d . . . C23 C 1.1893(3) 0.6189(2) 0.43641(9) 0.0220(5) Uani 1 1 d . . . H23 H 1.0906 0.5803 0.4498 0.026 Uiso 1 1 calc R . . C24 C 1.2473(3) 0.7397(2) 0.45985(10) 0.0257(6) Uani 1 1 d . . . H24 H 1.1882 0.7834 0.489 0.031 Uiso 1 1 calc R . . C25 C 1.3913(3) 0.7973(2) 0.44093(10) 0.0253(6) Uani 1 1 d . . . H25 H 1.4311 0.8804 0.4569 0.03 Uiso 1 1 calc R . . C26 C 1.4769(3) 0.7325(2) 0.39840(10) 0.0232(5) Uani 1 1 d . . . H26 H 1.5757 0.7712 0.3851 0.028 Uiso 1 1 calc R . . C27 C 1.4181(3) 0.6115(2) 0.37532(10) 0.0206(5) Uani 1 1 d . . . H27 H 1.4779 0.5674 0.3464 0.025 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 0.0268(9) 0.0170(8) 0.0217(9) 0.0041(7) 0.0042(7) -0.0024(7) C2 0.0228(12) 0.0169(11) 0.0152(11) 0.0012(9) -0.0038(10) -0.0051(10) N3 0.0172(9) 0.0142(8) 0.0171(10) -0.0002(8) 0.0020(8) 0.0008(7) C4 0.0200(12) 0.0133(10) 0.0174(11) -0.0013(9) 0.0034(9) -0.0007(9) C5 0.0232(12) 0.0185(11) 0.0184(12) -0.0001(9) 0.0044(10) -0.0040(10) O6 0.0274(9) 0.0164(8) 0.0266(9) 0.0016(7) -0.0037(7) 0.0013(7) C7 0.0165(11) 0.0176(10) 0.0165(11) -0.0034(9) 0.0001(9) 0.0020(9) C8 0.0151(11) 0.0175(10) 0.0184(11) -0.0016(9) 0.0010(9) 0.0004(9) C9 0.0162(11) 0.0165(10) 0.0166(11) 0.0003(10) 0.0028(9) -0.0003(9) C10 0.0165(11) 0.0150(10) 0.0273(13) 0.0017(10) -0.0049(10) -0.0012(9) C11 0.0176(12) 0.0213(11) 0.0268(13) 0.0072(10) -0.0055(10) -0.0028(10) C12 0.0250(13) 0.0293(13) 0.0183(12) 0.0023(10) 0.0022(10) -0.0012(11) C13 0.0211(12) 0.0215(11) 0.0175(12) -0.0026(10) 0.0033(10) -0.0006(10) C14 0.0194(11) 0.0137(10) 0.0157(11) -0.0038(9) 0.0022(9) 0.0027(9) C15 0.0209(12) 0.0217(11) 0.0233(13) 0.0023(10) -0.0038(10) -0.0021(10) C16 0.0253(13) 0.0198(11) 0.0375(15) 0.0003(11) -0.0070(12) -0.0042(10) C17 0.0268(13) 0.0235(12) 0.0302(14) -0.0096(11) -0.0098(11) 0.0045(11) C18 0.0332(14) 0.0238(12) 0.0179(12) -0.0039(11) -0.0034(10) 0.0125(12) C19 0.0235(12) 0.0161(11) 0.0184(12) -0.0001(10) 0.0055(10) 0.0044(10) C20 0.0313(15) 0.0187(11) 0.0401(16) 0.0024(11) -0.0043(13) 0.0068(11) C21 0.0193(12) 0.0154(10) 0.0196(12) 0.0010(9) 0.0030(10) 0.0010(9) C22 0.0194(12) 0.0182(11) 0.0160(11) 0.0031(9) -0.0012(9) 0.0032(9) C23 0.0220(12) 0.0249(12) 0.0193(12) 0.0001(10) 0.0005(10) 0.0025(10) C24 0.0309(14) 0.0249(12) 0.0214(12) -0.0059(11) 0.0008(10) 0.0009(11) C25 0.0303(14) 0.0207(11) 0.0247(13) -0.0002(10) -0.0071(11) -0.0002(11) C26 0.0216(12) 0.0233(11) 0.0247(13) 0.0033(11) -0.0028(10) -0.0043(10) C27 0.0212(12) 0.0212(11) 0.0193(12) 0.0022(10) 0.0008(10) 0.0050(9) #----------------------------------------------------------------------------# # 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 O1 C2 1.348(3) . ? O1 C5 1.452(2) . ? C2 O6 1.208(3) . ? C2 N3 1.375(3) . ? N3 C7 1.416(3) . ? N3 C4 1.472(3) . ? C4 C21 1.530(3) . ? C4 C5 1.533(3) . ? C4 H4 1 . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C7 C8 1.330(3) . ? C7 H7 0.95 . ? C8 C13 1.504(3) . ? C8 C9 1.514(3) . ? C9 C10 1.521(3) . ? C9 C14 1.538(3) . ? C9 H9 1 . ? C10 C11 1.328(3) . ? C10 C20 1.501(3) . ? C11 C12 1.496(3) . ? C11 H11 0.95 . ? C12 C13 1.531(3) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C15 1.384(3) . ? C14 C19 1.395(3) . ? C15 C16 1.387(3) . ? C15 H15 0.95 . ? C16 C17 1.382(3) . ? C16 H16 0.95 . ? C17 C18 1.388(3) . ? C17 H17 0.95 . ? C18 C19 1.389(3) . ? C18 H18 0.95 . ? C19 H19 0.95 . ? C20 H20A 0.98 . ? C20 H20B 0.98 . ? C20 H20C 0.98 . ? C21 C22 1.510(3) . ? C21 H21A 0.99 . ? C21 H21B 0.99 . ? C22 C23 1.390(3) . ? C22 C27 1.390(3) . ? C23 C24 1.383(3) . ? C23 H23 0.95 . ? C24 C25 1.386(3) . ? C24 H24 0.95 . ? C25 C26 1.387(3) . ? C25 H25 0.95 . ? C26 C27 1.384(3) . ? C26 H26 0.95 . ? C27 H27 0.95 . ? 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 O1 C5 109.13(16) . . ? O6 C2 O1 122.6(2) . . ? O6 C2 N3 127.2(2) . . ? O1 C2 N3 110.23(19) . . ? C2 N3 C7 117.52(18) . . ? C2 N3 C4 110.86(18) . . ? C7 N3 C4 126.95(17) . . ? N3 C4 C21 112.68(18) . . ? N3 C4 C5 99.94(17) . . ? C21 C4 C5 115.95(19) . . ? N3 C4 H4 109.3 . . ? C21 C4 H4 109.3 . . ? C5 C4 H4 109.3 . . ? O1 C5 C4 105.85(17) . . ? O1 C5 H5A 110.6 . . ? C4 C5 H5A 110.6 . . ? O1 C5 H5B 110.6 . . ? C4 C5 H5B 110.6 . . ? H5A C5 H5B 108.7 . . ? C8 C7 N3 128.59(19) . . ? C8 C7 H7 115.7 . . ? N3 C7 H7 115.7 . . ? C7 C8 C13 119.87(19) . . ? C7 C8 C9 127.6(2) . . ? C13 C8 C9 112.52(17) . . ? C8 C9 C10 110.34(17) . . ? C8 C9 C14 109.11(17) . . ? C10 C9 C14 112.97(17) . . ? C8 C9 H9 108.1 . . ? C10 C9 H9 108.1 . . ? C14 C9 H9 108.1 . . ? C11 C10 C20 122.2(2) . . ? C11 C10 C9 122.0(2) . . ? C20 C10 C9 115.75(19) . . ? C10 C11 C12 125.0(2) . . ? C10 C11 H11 117.5 . . ? C12 C11 H11 117.5 . . ? C11 C12 C13 111.73(19) . . ? C11 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? C11 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 107.9 . . ? C8 C13 C12 110.24(19) . . ? C8 C13 H13A 109.6 . . ? C12 C13 H13A 109.6 . . ? C8 C13 H13B 109.6 . . ? C12 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? C15 C14 C19 118.1(2) . . ? C15 C14 C9 122.7(2) . . ? C19 C14 C9 119.24(19) . . ? C14 C15 C16 121.2(2) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? C17 C16 C15 120.1(2) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 119.7(2) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C17 C18 C19 119.7(2) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C18 C19 C14 121.1(2) . . ? C18 C19 H19 119.4 . . ? C14 C19 H19 119.4 . . ? C10 C20 H20A 109.5 . . ? C10 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C10 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C4 115.00(17) . . ? C22 C21 H21A 108.5 . . ? C4 C21 H21A 108.5 . . ? C22 C21 H21B 108.5 . . ? C4 C21 H21B 108.5 . . ? H21A C21 H21B 107.5 . . ? C23 C22 C27 118.1(2) . . ? C23 C22 C21 120.6(2) . . ? C27 C22 C21 121.3(2) . . ? C24 C23 C22 121.0(2) . . ? C24 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? C23 C24 C25 120.2(2) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C24 C25 C26 119.4(2) . . ? C24 C25 H25 120.3 . . ? C26 C25 H25 120.3 . . ? C27 C26 C25 119.9(2) . . ? C27 C26 H26 120 . . ? C25 C26 H26 120 . . ? C26 C27 C22 121.3(2) . . ? C26 C27 H27 119.4 . . ? C22 C27 H27 119.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 O1 C2 O6 -175.7(2) . . . . ? C5 O1 C2 N3 2.4(2) . . . . ? O6 C2 N3 C7 -13.4(3) . . . . ? O1 C2 N3 C7 168.63(17) . . . . ? O6 C2 N3 C4 -170.9(2) . . . . ? O1 C2 N3 C4 11.1(2) . . . . ? C2 N3 C4 C21 105.2(2) . . . . ? C7 N3 C4 C21 -49.7(3) . . . . ? C2 N3 C4 C5 -18.5(2) . . . . ? C7 N3 C4 C5 -173.35(19) . . . . ? C2 O1 C5 C4 -14.1(2) . . . . ? N3 C4 C5 O1 18.9(2) . . . . ? C21 C4 C5 O1 -102.4(2) . . . . ? C2 N3 C7 C8 162.9(2) . . . . ? C4 N3 C7 C8 -43.6(3) . . . . ? N3 C7 C8 C13 176.4(2) . . . . ? N3 C7 C8 C9 -3.4(4) . . . . ? C7 C8 C9 C10 131.5(2) . . . . ? C13 C8 C9 C10 -48.3(2) . . . . ? C7 C8 C9 C14 -103.8(3) . . . . ? C13 C8 C9 C14 76.4(2) . . . . ? C8 C9 C10 C11 18.3(3) . . . . ? C14 C9 C10 C11 -104.2(2) . . . . ? C8 C9 C10 C20 -160.2(2) . . . . ? C14 C9 C10 C20 77.4(2) . . . . ? C20 C10 C11 C12 176.7(2) . . . . ? C9 C10 C11 C12 -1.6(4) . . . . ? C10 C11 C12 C13 13.8(3) . . . . ? C7 C8 C13 C12 -117.8(2) . . . . ? C9 C8 C13 C12 62.0(2) . . . . ? C11 C12 C13 C8 -42.4(3) . . . . ? C8 C9 C14 C15 -114.4(2) . . . . ? C10 C9 C14 C15 8.7(3) . . . . ? C8 C9 C14 C19 66.1(2) . . . . ? C10 C9 C14 C19 -170.73(19) . . . . ? C19 C14 C15 C16 0.8(3) . . . . ? C9 C14 C15 C16 -178.6(2) . . . . ? C14 C15 C16 C17 -0.4(4) . . . . ? C15 C16 C17 C18 -0.8(4) . . . . ? C16 C17 C18 C19 1.5(3) . . . . ? C17 C18 C19 C14 -1.1(3) . . . . ? C15 C14 C19 C18 -0.1(3) . . . . ? C9 C14 C19 C18 179.35(19) . . . . ? N3 C4 C21 C22 -58.7(2) . . . . ? C5 C4 C21 C22 55.6(3) . . . . ? C4 C21 C22 C23 90.9(3) . . . . ? C4 C21 C22 C27 -89.6(3) . . . . ? C27 C22 C23 C24 0.5(3) . . . . ? C21 C22 C23 C24 -179.9(2) . . . . ? C22 C23 C24 C25 -0.1(3) . . . . ? C23 C24 C25 C26 -0.1(3) . . . . ? C24 C25 C26 C27 0.0(3) . . . . ? C25 C26 C27 C22 0.5(3) . . . . ? C23 C22 C27 C26 -0.7(3) . . . . ? C21 C22 C27 C26 179.8(2) . . . . ? # END of CIF # Attachment '- ccdc_deposit 3hi.cif' data_lm15hff1n _database_code_depnum_ccdc_archive 'CCDC 804850' #TrackingRef '- ccdc_deposit 3hi.cif' _audit_creation_date 2010-10-24T01:59:19-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common HF250a784 _chemical_formula_moiety 'C24 H25 N O2' _chemical_formula_sum 'C24 H25 N O2' _chemical_formula_weight 359.45 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _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 8.2075(3) _cell_length_b 9.8258(4) _cell_length_c 24.0803(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1941.96(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2628 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 24.80 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.32 _exptl_crystal_density_diffrn 1.229 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8855 _exptl_absorpt_correction_T_max 0.9721 _exptl_absorpt_process_details 'BRUKER AXS - SADABS' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Bruker X8 kappa APEXII CCD' _diffrn_measurement_method 'omega and phi scans' _diffrn_reflns_av_R_equivalents 0.0631 _diffrn_reflns_av_unetI/netI 0.0554 _diffrn_reflns_number 18458 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 30.56 _diffrn_reflns_theta_full 30.56 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _reflns_number_total 3339 _reflns_number_gt 2664 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 v2010.9-1 (Bruker AXS, 2010)' _computing_cell_refinement 'APEX2 v2010.9-1 (Bruker AXS, 2010)' _computing_data_reduction 'APEX2 v2010.9-1 (Bruker AXS, 2010)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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^)+(0.0470P)^2^+0.4849P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3339 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0701 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.111 _refine_ls_wR_factor_gt 0.1023 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.25 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.057 #----------------------------------------------------------------------------# # 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 0.2976(2) 0.77272(16) 0.01690(5) 0.0180(3) Uani 1 1 d . . . C2 C 0.3631(3) 0.8750(2) 0.04778(9) 0.0153(4) Uani 1 1 d . . . N3 N 0.3406(2) 0.84791(19) 0.10284(7) 0.0148(4) Uani 1 1 d . . . C4 C 0.2291(3) 0.7332(2) 0.11116(8) 0.0163(4) Uani 1 1 d . . . H4 H 0.1178 0.7688 0.1199 0.02 Uiso 1 1 calc R . . C5 C 0.2280(3) 0.6683(2) 0.05241(8) 0.0161(4) Uani 1 1 d . . . H5 H 0.1126 0.6515 0.0409 0.019 Uiso 1 1 calc R . . O6 O 0.4321(2) 0.97018(16) 0.02653(6) 0.0188(3) Uani 1 1 d . . . C7 C 0.3599(3) 0.9443(2) 0.14661(8) 0.0167(4) Uani 1 1 d . . . H7 H 0.2645 0.965 0.1673 0.02 Uiso 1 1 calc R . . C8 C 0.4942(3) 1.0083(2) 0.16196(8) 0.0173(4) Uani 1 1 d . . . C9 C 0.6618(3) 0.9926(2) 0.13541(8) 0.0163(4) Uani 1 1 d . . . H9 H 0.6445 0.9751 0.0949 0.02 Uiso 1 1 calc R . . C10 C 0.7647(3) 1.1203(2) 0.14039(9) 0.0195(5) Uani 1 1 d . . . C11 C 0.7146(3) 1.2307(3) 0.16723(9) 0.0259(5) Uani 1 1 d . . . H11 H 0.785 1.3075 0.1676 0.031 Uiso 1 1 calc R . . C12 C 0.5552(3) 1.2429(3) 0.19694(10) 0.0274(6) Uani 1 1 d . . . H12A H 0.4762 1.2917 0.1731 0.033 Uiso 1 1 calc R . . H12B H 0.5702 1.2963 0.2314 0.033 Uiso 1 1 calc R . . C13 C 0.4882(3) 1.1022(2) 0.21133(9) 0.0231(5) Uani 1 1 d . . . H13A H 0.5529 1.0626 0.242 0.028 Uiso 1 1 calc R . . H13B H 0.3741 1.1111 0.2242 0.028 Uiso 1 1 calc R . . C14 C 0.7464(3) 0.8680(2) 0.15947(9) 0.0173(4) Uani 1 1 d . . . C15 C 0.8205(3) 0.8707(3) 0.21169(9) 0.0243(5) Uani 1 1 d . . . H15 H 0.8224 0.953 0.2324 0.029 Uiso 1 1 calc R . . C16 C 0.8915(3) 0.7540(3) 0.23361(11) 0.0324(6) Uani 1 1 d . . . H16 H 0.9415 0.7569 0.2692 0.039 Uiso 1 1 calc R . . C17 C 0.8895(3) 0.6338(3) 0.20379(12) 0.0333(6) Uani 1 1 d . . . H17 H 0.9361 0.5537 0.2192 0.04 Uiso 1 1 calc R . . C18 C 0.8199(3) 0.6300(3) 0.15183(12) 0.0320(6) Uani 1 1 d . . . H18 H 0.82 0.5478 0.131 0.038 Uiso 1 1 calc R . . C19 C 0.7495(3) 0.7467(3) 0.12990(10) 0.0240(5) Uani 1 1 d . . . H19 H 0.7024 0.7435 0.0939 0.029 Uiso 1 1 calc R . . C20 C 0.9232(3) 1.1158(3) 0.10911(10) 0.0293(6) Uani 1 1 d . . . H20A H 0.9822 1.2015 0.1147 0.044 Uiso 1 1 calc R . . H20B H 0.9014 1.1031 0.0694 0.044 Uiso 1 1 calc R . . H20C H 0.9895 1.04 0.1228 0.044 Uiso 1 1 calc R . . C21 C 0.2853(3) 0.6412(2) 0.15814(8) 0.0205(5) Uani 1 1 d . . . H21A H 0.3998 0.6166 0.1524 0.031 Uiso 1 1 calc R . . H21B H 0.2186 0.5585 0.1587 0.031 Uiso 1 1 calc R . . H21C H 0.2738 0.6891 0.1936 0.031 Uiso 1 1 calc R . . C22 C 0.3228(3) 0.5382(2) 0.04685(8) 0.0156(4) Uani 1 1 d . . . C23 C 0.4904(3) 0.5376(2) 0.03802(8) 0.0173(4) Uani 1 1 d . . . H23 H 0.5464 0.621 0.0323 0.021 Uiso 1 1 calc R . . C24 C 0.5762(3) 0.4160(2) 0.03754(8) 0.0203(5) Uani 1 1 d . . . H24 H 0.6907 0.4168 0.0318 0.024 Uiso 1 1 calc R . . C25 C 0.4964(3) 0.2939(2) 0.04536(9) 0.0211(5) Uani 1 1 d . . . H25 H 0.5556 0.2109 0.0452 0.025 Uiso 1 1 calc R . . C26 C 0.3291(3) 0.2933(2) 0.05349(9) 0.0219(5) Uani 1 1 d . . . H26 H 0.2736 0.2095 0.0588 0.026 Uiso 1 1 calc R . . C27 C 0.2423(3) 0.4146(2) 0.05390(9) 0.0197(5) Uani 1 1 d . . . H27 H 0.1275 0.4133 0.059 0.024 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 0.0259(9) 0.0144(8) 0.0136(7) 0.0015(6) -0.0037(6) -0.0019(7) C2 0.0155(10) 0.0140(10) 0.0164(9) -0.0003(8) -0.0015(8) 0.0045(9) N3 0.0142(8) 0.0152(9) 0.0151(8) -0.0026(7) -0.0005(7) -0.0016(8) C4 0.0143(10) 0.0165(11) 0.0182(9) 0.0007(8) -0.0006(8) -0.0005(10) C5 0.0178(11) 0.0135(10) 0.0171(9) 0.0013(8) -0.0037(9) -0.0022(9) O6 0.0215(8) 0.0158(8) 0.0191(7) 0.0022(6) 0.0010(7) -0.0002(7) C7 0.0169(10) 0.0198(11) 0.0136(9) -0.0043(8) 0.0012(8) 0.0027(10) C8 0.0196(10) 0.0190(11) 0.0133(9) -0.0025(8) -0.0018(8) 0.0030(10) C9 0.0166(10) 0.0187(11) 0.0136(9) -0.0016(8) -0.0022(8) -0.0015(10) C10 0.0216(11) 0.0209(11) 0.0159(9) 0.0055(8) -0.0069(9) -0.0038(10) C11 0.0315(14) 0.0208(12) 0.0253(11) 0.0015(9) -0.0090(10) -0.0055(12) C12 0.0376(15) 0.0199(12) 0.0248(11) -0.0069(10) -0.0082(11) 0.0029(12) C13 0.0253(12) 0.0265(13) 0.0175(10) -0.0104(9) -0.0015(9) -0.0013(11) C14 0.0115(9) 0.0199(11) 0.0205(10) 0.0011(9) 0.0007(9) -0.0024(9) C15 0.0221(12) 0.0296(13) 0.0212(11) 0.0016(10) -0.0028(10) -0.0011(12) C16 0.0231(13) 0.0454(17) 0.0287(12) 0.0145(12) -0.0026(11) 0.0024(13) C17 0.0201(12) 0.0309(15) 0.0490(16) 0.0171(13) 0.0066(12) 0.0045(12) C18 0.0223(12) 0.0225(13) 0.0514(16) -0.0004(12) 0.0048(12) 0.0000(12) C19 0.0170(11) 0.0252(12) 0.0297(12) -0.0043(10) -0.0015(10) -0.0003(11) C20 0.0246(12) 0.0324(14) 0.0309(13) 0.0057(11) 0.0017(11) -0.0087(13) C21 0.0252(12) 0.0221(12) 0.0140(9) 0.0020(9) 0.0006(9) 0.0021(11) C22 0.0187(10) 0.0162(10) 0.0120(9) -0.0004(8) -0.0027(8) -0.0001(10) C23 0.0196(11) 0.0155(10) 0.0167(9) -0.0003(8) -0.0022(9) -0.0037(10) C24 0.0196(11) 0.0226(12) 0.0186(10) -0.0023(9) -0.0005(9) 0.0014(11) C25 0.0279(12) 0.0172(11) 0.0183(10) -0.0009(9) -0.0019(10) 0.0051(11) C26 0.0280(13) 0.0146(11) 0.0231(10) 0.0016(9) -0.0032(10) -0.0043(11) C27 0.0184(11) 0.0187(11) 0.0220(10) -0.0025(9) -0.0019(9) -0.0027(10) #----------------------------------------------------------------------------# # 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 O1 C2 1.361(3) . ? O1 C5 1.453(3) . ? C2 O6 1.207(3) . ? C2 N3 1.365(3) . ? N3 C7 1.425(3) . ? N3 C4 1.466(3) . ? C4 C21 1.520(3) . ? C4 C5 1.552(3) . ? C4 H4 1 . ? C5 C22 1.502(3) . ? C5 H5 1 . ? C7 C8 1.322(3) . ? C7 H7 0.95 . ? C8 C13 1.506(3) . ? C8 C9 1.525(3) . ? C9 C10 1.518(3) . ? C9 C14 1.522(3) . ? C9 H9 1 . ? C10 C11 1.328(3) . ? C10 C20 1.504(3) . ? C11 C12 1.496(4) . ? C11 H11 0.95 . ? C12 C13 1.528(4) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C19 1.388(3) . ? C14 C15 1.397(3) . ? C15 C16 1.390(4) . ? C15 H15 0.95 . ? C16 C17 1.383(4) . ? C16 H16 0.95 . ? C17 C18 1.376(4) . ? C17 H17 0.95 . ? C18 C19 1.388(4) . ? C18 H18 0.95 . ? C19 H19 0.95 . ? C20 H20A 0.98 . ? C20 H20B 0.98 . ? C20 H20C 0.98 . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? C22 C23 1.392(3) . ? C22 C27 1.393(3) . ? C23 C24 1.386(3) . ? C23 H23 0.95 . ? C24 C25 1.380(3) . ? C24 H24 0.95 . ? C25 C26 1.386(4) . ? C25 H25 0.95 . ? C26 C27 1.389(3) . ? C26 H26 0.95 . ? C27 H27 0.95 . ? 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 O1 C5 110.83(15) . . ? O6 C2 O1 121.75(19) . . ? O6 C2 N3 128.8(2) . . ? O1 C2 N3 109.48(18) . . ? C2 N3 C7 125.02(19) . . ? C2 N3 C4 111.52(17) . . ? C7 N3 C4 118.62(17) . . ? N3 C4 C21 111.67(18) . . ? N3 C4 C5 101.26(16) . . ? C21 C4 C5 115.84(18) . . ? N3 C4 H4 109.2 . . ? C21 C4 H4 109.2 . . ? C5 C4 H4 109.2 . . ? O1 C5 C22 110.18(18) . . ? O1 C5 C4 104.11(16) . . ? C22 C5 C4 115.34(17) . . ? O1 C5 H5 109 . . ? C22 C5 H5 109 . . ? C4 C5 H5 109 . . ? C8 C7 N3 128.0(2) . . ? C8 C7 H7 116 . . ? N3 C7 H7 116 . . ? C7 C8 C13 119.0(2) . . ? C7 C8 C9 125.91(19) . . ? C13 C8 C9 115.01(19) . . ? C10 C9 C14 112.42(18) . . ? C10 C9 C8 112.65(19) . . ? C14 C9 C8 109.48(18) . . ? C10 C9 H9 107.3 . . ? C14 C9 H9 107.3 . . ? C8 C9 H9 107.3 . . ? C11 C10 C20 122.4(2) . . ? C11 C10 C9 122.8(2) . . ? C20 C10 C9 114.7(2) . . ? C10 C11 C12 124.7(2) . . ? C10 C11 H11 117.7 . . ? C12 C11 H11 117.7 . . ? C11 C12 C13 110.6(2) . . ? C11 C12 H12A 109.5 . . ? C13 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? C8 C13 C12 111.32(19) . . ? C8 C13 H13A 109.4 . . ? C12 C13 H13A 109.4 . . ? C8 C13 H13B 109.4 . . ? C12 C13 H13B 109.4 . . ? H13A C13 H13B 108 . . ? C19 C14 C15 118.0(2) . . ? C19 C14 C9 120.25(19) . . ? C15 C14 C9 121.7(2) . . ? C16 C15 C14 120.6(2) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C17 C16 C15 120.2(2) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C18 C17 C16 120.0(3) . . ? C18 C17 H17 120 . . ? C16 C17 H17 120 . . ? C17 C18 C19 119.8(3) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C14 C19 C18 121.4(2) . . ? C14 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C10 C20 H20A 109.5 . . ? C10 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C10 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C4 C21 H21A 109.5 . . ? C4 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C4 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C27 118.9(2) . . ? C23 C22 C5 121.9(2) . . ? C27 C22 C5 119.0(2) . . ? C24 C23 C22 120.4(2) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C25 C24 C23 120.5(2) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C24 C25 C26 119.5(2) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C25 C26 C27 120.4(2) . . ? C25 C26 H26 119.8 . . ? C27 C26 H26 119.8 . . ? C26 C27 C22 120.3(2) . . ? C26 C27 H27 119.9 . . ? C22 C27 H27 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 O1 C2 O6 177.6(2) . . . . ? C5 O1 C2 N3 -0.9(2) . . . . ? O6 C2 N3 C7 16.4(4) . . . . ? O1 C2 N3 C7 -165.29(19) . . . . ? O6 C2 N3 C4 171.3(2) . . . . ? O1 C2 N3 C4 -10.4(2) . . . . ? C2 N3 C4 C21 140.02(19) . . . . ? C7 N3 C4 C21 -63.3(2) . . . . ? C2 N3 C4 C5 16.1(2) . . . . ? C7 N3 C4 C5 172.78(18) . . . . ? C2 O1 C5 C22 -113.47(19) . . . . ? C2 O1 C5 C4 10.8(2) . . . . ? N3 C4 C5 O1 -15.5(2) . . . . ? C21 C4 C5 O1 -136.45(19) . . . . ? N3 C4 C5 C22 105.4(2) . . . . ? C21 C4 C5 C22 -15.6(3) . . . . ? C2 N3 C7 C8 -63.6(3) . . . . ? C4 N3 C7 C8 143.2(2) . . . . ? N3 C7 C8 C13 -177.4(2) . . . . ? N3 C7 C8 C9 0.1(4) . . . . ? C7 C8 C9 C10 151.0(2) . . . . ? C13 C8 C9 C10 -31.4(3) . . . . ? C7 C8 C9 C14 -83.1(3) . . . . ? C13 C8 C9 C14 94.4(2) . . . . ? C14 C9 C10 C11 -121.5(2) . . . . ? C8 C9 C10 C11 2.7(3) . . . . ? C14 C9 C10 C20 62.6(2) . . . . ? C8 C9 C10 C20 -173.15(18) . . . . ? C20 C10 C11 C12 177.3(2) . . . . ? C9 C10 C11 C12 1.7(4) . . . . ? C10 C11 C12 C13 21.4(3) . . . . ? C7 C8 C13 C12 -127.1(2) . . . . ? C9 C8 C13 C12 55.2(3) . . . . ? C11 C12 C13 C8 -48.1(3) . . . . ? C10 C9 C14 C19 -133.3(2) . . . . ? C8 C9 C14 C19 100.7(2) . . . . ? C10 C9 C14 C15 47.6(3) . . . . ? C8 C9 C14 C15 -78.4(3) . . . . ? C19 C14 C15 C16 -1.5(3) . . . . ? C9 C14 C15 C16 177.5(2) . . . . ? C14 C15 C16 C17 0.1(4) . . . . ? C15 C16 C17 C18 1.2(4) . . . . ? C16 C17 C18 C19 -1.0(4) . . . . ? C15 C14 C19 C18 1.8(4) . . . . ? C9 C14 C19 C18 -177.3(2) . . . . ? C17 C18 C19 C14 -0.5(4) . . . . ? O1 C5 C22 C23 34.3(3) . . . . ? C4 C5 C22 C23 -83.2(3) . . . . ? O1 C5 C22 C27 -149.45(19) . . . . ? C4 C5 C22 C27 93.1(2) . . . . ? C27 C22 C23 C24 -1.5(3) . . . . ? C5 C22 C23 C24 174.78(19) . . . . ? C22 C23 C24 C25 0.5(3) . . . . ? C23 C24 C25 C26 0.3(3) . . . . ? C24 C25 C26 C27 -0.2(4) . . . . ? C25 C26 C27 C22 -0.8(3) . . . . ? C23 C22 C27 C26 1.6(3) . . . . ? C5 C22 C27 C26 -174.7(2) . . . . ? # END of CIF