# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef 'deposit_Macchi.cif' #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2009-07-08 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #============================================================================== # # SUBMISSION DETAILS _publ_contact_author_name 'Macchi, P.' # Name of author for correspondence _publ_contact_author_address ;Department of Chemistry and Biochemistry University of Bern freiestarsse Bern Switzerland ; # Address of author for correspondence _publ_contact_author_email piero.macchi@dcb.unibe.ch _publ_requested_category FM loop_ _publ_author_name 'Mohamed Hagar' 'Fabio Ragaini' 'Elena Monticelli' 'Alessandro Caselli' 'Piero Macchi' 'Nicola Casati' data_1R,2R,2'S-4 _database_code_depnum_ccdc_archive 'CCDC 780454' _audit_creation_date 2009-07-24T18:54:47-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C34 H40 Cl2 N2 Zn' _chemical_formula_weight 612.95 _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' 'x-y, -y, -z+1/3' '-x, -x+y, -z+2/3' 'y, x, -z' _cell_length_a 11.573(4) _cell_length_b 11.573 _cell_length_c 19.653(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 2279.6(12) _cell_formula_units_Z 3 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 410 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 13 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 966 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.01 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.696 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.1616 _diffrn_reflns_av_unetI/netI 0.101 _diffrn_reflns_number 11007 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 20.76 _diffrn_reflns_theta_full 20.76 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 1577 _reflns_number_gt 1018 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0337P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1577 _refine_ls_number_parameters 178 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1042 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.0946 _refine_ls_wR_factor_gt 0.0798 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(3) _refine_diff_density_max 0.207 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.055 #----------------------------------------------------------------------------# # 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 '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 0.6888(9) 0.0550(8) 0.1399(4) 0.039(2) Uani 1 1 d . . . C11 C 0.6578(10) 0.2068(10) 0.0708(5) 0.056(3) Uani 1 1 d . . . H11 H 0.6971 0.1964 0.0287 0.067 Uiso 1 1 calc R . . C12 C 0.5743(10) 0.2705(9) 0.0654(5) 0.066(3) Uani 1 1 d . . . H12A H 0.4974 0.2382 0.0952 0.079 Uiso 1 1 calc R . . H12B H 0.5621 0.2978 0.0205 0.079 Uiso 1 1 calc R . . C13 C 0.7110(11) 0.3476(10) 0.0973(5) 0.056(3) Uani 1 1 d . . . C14 C 0.7317(10) 0.3646(10) 0.1756(4) 0.065(3) Uani 1 1 d . . . H14A H 0.6457 0.3308 0.1976 0.079 Uiso 1 1 calc R . . H14B H 0.7706 0.3122 0.1915 0.079 Uiso 1 1 calc R . . C15 C 0.8239(9) 0.5128(9) 0.1962(5) 0.068(3) Uani 1 1 d . . . H15A H 0.7695 0.5504 0.2106 0.081 Uiso 1 1 calc R . . H15B H 0.8789 0.5171 0.2344 0.081 Uiso 1 1 calc R . . C16 C 0.9136(10) 0.5955(9) 0.1375(5) 0.071(3) Uani 1 1 d . . . H16 H 0.9874 0.6837 0.1501 0.086 Uiso 1 1 calc R . . C17 C 0.9536(10) 0.5079(10) 0.0945(5) 0.067(3) Uani 1 1 d . . . H17A H 0.9596 0.4397 0.1203 0.08 Uiso 1 1 calc R . . H17B H 1.0319 0.5585 0.0663 0.08 Uiso 1 1 calc R . . C18 C 0.8187(10) 0.4571(10) 0.0563(5) 0.063(3) Uani 1 1 d . . . H18 H 0.8192 0.4392 0.0076 0.076 Uiso 1 1 calc R . . C19 C 0.8258(10) 0.5937(10) 0.0755(5) 0.059(3) Uani 1 1 d . . . C21 C 0.8243(11) 0.0824(9) 0.1235(4) 0.045(2) Uani 1 1 d . . . C22 C 0.9213(10) 0.1645(9) 0.0788(5) 0.050(3) Uani 1 1 d . . . H22 H 0.9076 0.2202 0.0499 0.06 Uiso 1 1 calc R . . C23 C 1.0430(10) 0.1633(9) 0.0772(5) 0.057(3) Uani 1 1 d . . . H23 H 1.1085 0.2187 0.0465 0.068 Uiso 1 1 calc R . . C24 C 1.0682(10) 0.0841(10) 0.1190(5) 0.057(3) Uani 1 1 d . . . H24 H 1.149 0.0853 0.1162 0.068 Uiso 1 1 calc R . . C25 C 0.9697(14) 0 0.1667 0.048(4) Uani 1 2 d S . . C26 C 0.8519(13) 0 0.1667 0.041(4) Uani 1 2 d S . . C110 C 0.6962(9) 0.5893(8) 0.0904(5) 0.076(3) Uani 1 1 d . . . H11A H 0.6472 0.5217 0.1239 0.113 Uiso 1 1 calc R . . H11B H 0.6444 0.569 0.0495 0.113 Uiso 1 1 calc R . . H11C H 0.7141 0.6744 0.1075 0.113 Uiso 1 1 calc R . . C111 C 0.9051(9) 0.7000(9) 0.0227(5) 0.085(3) Uani 1 1 d . . . H11D H 0.9867 0.7005 0.0131 0.128 Uiso 1 1 calc R . . H11E H 0.9253 0.7858 0.0399 0.128 Uiso 1 1 calc R . . H11F H 0.8536 0.6811 -0.0183 0.128 Uiso 1 1 calc R . . N1 N 0.6140(7) 0.1024(8) 0.1200(3) 0.043(2) Uani 1 1 d . . . Cl1 Cl 0.2703(2) -0.1097(3) 0.09073(10) 0.0686(9) Uani 1 1 d . . . Zn1 Zn 0.42816(13) 0 0.1667 0.0536(5) Uani 1 2 d S . . 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 0.041(7) 0.036(7) 0.026(6) -0.013(4) -0.005(5) 0.009(6) C11 0.061(8) 0.046(8) 0.056(7) 0.009(6) -0.011(6) 0.024(7) C12 0.066(9) 0.070(7) 0.080(7) 0.025(6) 0.007(7) 0.047(8) C13 0.059(8) 0.046(8) 0.060(8) 0.014(6) 0.009(6) 0.025(7) C14 0.076(9) 0.056(8) 0.047(7) -0.008(6) 0.008(6) 0.020(7) C15 0.088(9) 0.052(8) 0.069(8) 0.008(6) 0.004(7) 0.040(7) C16 0.093(9) 0.051(8) 0.058(8) 0.002(6) 0.013(7) 0.027(7) C17 0.055(8) 0.067(8) 0.082(8) 0.009(6) 0.008(7) 0.034(6) C18 0.066(8) 0.058(8) 0.067(8) 0.006(7) 0.013(7) 0.032(7) C19 0.059(8) 0.055(8) 0.064(7) 0.012(7) 0.011(7) 0.029(6) C21 0.044(8) 0.041(6) 0.043(6) -0.010(5) 0.000(6) 0.016(7) C22 0.049(7) 0.050(7) 0.052(6) -0.005(6) -0.013(6) 0.025(6) C23 0.054(8) 0.040(7) 0.059(7) 0.004(6) 0.013(6) 0.011(6) C24 0.039(7) 0.057(9) 0.066(8) -0.008(7) 0.016(7) 0.018(6) C25 0.054(9) 0.050(11) 0.040(10) -0.007(8) -0.004(4) 0.025(5) C26 0.039(8) 0.052(12) 0.038(10) -0.018(8) -0.009(4) 0.026(6) C110 0.082(8) 0.087(8) 0.085(8) 0.006(6) 0.019(6) 0.062(6) C111 0.091(8) 0.064(8) 0.085(8) 0.019(7) 0.017(7) 0.026(7) N1 0.042(5) 0.052(6) 0.038(5) -0.005(5) -0.008(4) 0.026(5) Cl1 0.0655(18) 0.083(2) 0.0582(16) -0.0141(15) -0.0192(14) 0.0378(15) Zn1 0.0523(8) 0.0672(12) 0.0463(9) -0.0090(9) -0.0045(5) 0.0336(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C2 N1 1.296(9) . ? C2 C21 1.472(12) . ? C2 C2 1.524(15) 4 ? C11 N1 1.428(11) . ? C11 C12 1.484(11) . ? C11 C13 1.516(12) . ? C12 C13 1.511(12) . ? C13 C18 1.492(11) . ? C13 C14 1.555(11) . ? C14 C15 1.553(11) . ? C15 C16 1.526(11) . ? C16 C17 1.557(11) . ? C16 C19 1.581(11) . ? C17 C18 1.559(12) . ? C18 C19 1.588(12) . ? C19 C110 1.504(11) . ? C19 C111 1.518(11) . ? C21 C22 1.367(11) . ? C21 C26 1.426(11) . ? C22 C23 1.416(11) . ? C23 C24 1.365(12) . ? C24 C25 1.420(10) . ? C25 C26 1.364(15) . ? C25 C24 1.420(10) 4 ? C26 C21 1.426(11) 4 ? N1 Zn1 2.079(7) . ? Cl1 Zn1 2.204(2) . ? Zn1 N1 2.079(7) 4 ? Zn1 Cl1 2.204(2) 4 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C2 C21 135.1(8) . . ? N1 C2 C2 118.3(5) . 4 ? C21 C2 C2 106.6(5) . 4 ? N1 C11 C12 115.2(9) . . ? N1 C11 C13 117.3(9) . . ? C12 C11 C13 60.5(6) . . ? C11 C12 C13 60.8(6) . . ? C18 C13 C12 117.4(8) . . ? C18 C13 C11 116.4(9) . . ? C12 C13 C11 58.7(6) . . ? C18 C13 C14 114.6(9) . . ? C12 C13 C14 122.3(9) . . ? C11 C13 C14 115.4(9) . . ? C15 C14 C13 112.0(8) . . ? C16 C15 C14 111.8(7) . . ? C15 C16 C17 109.4(8) . . ? C15 C16 C19 110.1(8) . . ? C17 C16 C19 88.3(6) . . ? C16 C17 C18 86.6(7) . . ? C13 C18 C17 108.3(8) . . ? C13 C18 C19 108.8(8) . . ? C17 C18 C19 88.0(7) . . ? C110 C19 C111 110.5(8) . . ? C110 C19 C16 118.3(8) . . ? C111 C19 C16 113.1(8) . . ? C110 C19 C18 117.3(9) . . ? C111 C19 C18 110.7(8) . . ? C16 C19 C18 84.8(7) . . ? C22 C21 C26 117.9(10) . . ? C22 C21 C2 134.9(9) . . ? C26 C21 C2 107.2(10) . . ? C21 C22 C23 118.8(9) . . ? C24 C23 C22 122.8(10) . . ? C23 C24 C25 119.3(10) . . ? C26 C25 C24 117.4(8) . 4 ? C26 C25 C24 117.4(8) . . ? C24 C25 C24 125.2(16) 4 . ? C25 C26 C21 123.9(7) . 4 ? C25 C26 C21 123.9(7) . . ? C21 C26 C21 112.2(13) 4 . ? C2 N1 C11 122.2(8) . . ? C2 N1 Zn1 110.2(6) . . ? C11 N1 Zn1 127.5(6) . . ? N1 Zn1 N1 82.9(5) 4 . ? N1 Zn1 Cl1 110.69(18) 4 4 ? N1 Zn1 Cl1 117.2(2) . 4 ? N1 Zn1 Cl1 117.2(2) 4 . ? N1 Zn1 Cl1 110.69(18) . . ? Cl1 Zn1 Cl1 114.48(14) 4 . ? #END #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2009-07-24 at 19:25:07 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : fr31n archive31 data_1R,2R,2'S-3 _database_code_depnum_ccdc_archive 'CCDC 780455' #TrackingRef 'deposit_Macchi.cif' _audit_creation_date 2009-07-24T19:25:07-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C17 H22 N4 O7' _chemical_formula_weight 394.39 _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# 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 7.033(3) _cell_length_b 11.108(4) _cell_length_c 24.782(9) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(5) _cell_angle_gamma 90.000(5) _cell_volume 1936.1(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2909 _cell_measurement_theta_min 3 _cell_measurement_theta_max 19.5 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.867 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_unetI/netI 0.035 _diffrn_reflns_number 15810 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 23.25 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 2783 _reflns_number_gt 2235 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1172P)^2^+1.1010P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2783 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0944 _refine_ls_R_factor_gt 0.0774 _refine_ls_wR_factor_ref 0.2101 _refine_ls_wR_factor_gt 0.1969 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(3) _refine_diff_density_max 0.637 _refine_diff_density_min -0.269 _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 C1 C -0.2705(7) -0.2458(4) -0.65140(17) 0.0462(12) Uani 1 1 d . . . C4 C -0.6050(6) 0.0709(4) -0.56573(19) 0.0466(12) Uani 1 1 d . . . C7 C -0.4973(6) -0.0077(4) -0.53209(19) 0.0465(12) Uani 1 1 d . . . C8 C -0.2042(9) -0.1396(4) -0.68388(18) 0.0624(15) Uani 1 1 d . . . H8 H -0.0818 -0.1047 -0.6733 0.075 Uiso 1 1 calc R . . C9 C -0.3601(8) 0.2156(4) -0.5705(2) 0.0528(13) Uani 1 1 d . . . C12 C -0.5372(8) 0.1768(5) -0.5852(2) 0.0603(14) Uani 1 1 d . . . H12 H -0.611 0.2228 -0.6086 0.072 Uiso 1 1 calc R . . C15 C -0.2563(7) 0.1538(4) -0.5339(2) 0.0552(13) Uani 1 1 d . . . H15 H -0.1416 0.1846 -0.5214 0.066 Uiso 1 1 calc R . . C16 C -0.3225(7) 0.0448(4) -0.51543(19) 0.0491(12) Uani 1 1 d . . . C17 C -0.4373(11) -0.1260(7) -0.7356(3) 0.092(2) Uani 1 1 d . . . H17 H -0.4956 -0.0801 -0.765 0.111 Uiso 1 1 calc R . . C18 C -0.4757(10) -0.2825(7) -0.6620(3) 0.091(2) Uani 1 1 d . . . H18A H -0.5543 -0.2561 -0.6321 0.11 Uiso 1 1 calc R . . H18B H -0.4832 -0.3696 -0.6639 0.11 Uiso 1 1 calc R . . C21 C -0.2333(12) -0.1619(5) -0.7454(2) 0.082(2) Uani 1 1 d . . . C23 C -0.1271(16) -0.0684(9) -0.7793(3) 0.141(4) Uani 1 1 d . . . H28A H -0.1526 0.0107 -0.7655 0.212 Uiso 1 1 calc R . . H28B H -0.1691 -0.0733 -0.8161 0.212 Uiso 1 1 calc R . . H28C H 0.007 -0.084 -0.7777 0.212 Uiso 1 1 calc R . . C24 C -0.5550(13) -0.2284(10) -0.7152(3) 0.135(4) Uani 1 1 d . . . H24A H -0.5595 -0.2909 -0.7425 0.162 Uiso 1 1 calc R . . H24B H -0.6839 -0.2005 -0.7091 0.162 Uiso 1 1 calc R . . C27 C -0.3721(13) -0.0509(6) -0.6887(3) 0.103(3) Uani 1 1 d . . . H27A H -0.4579 -0.0516 -0.658 0.124 Uiso 1 1 calc R . . H27B H -0.3353 0.0306 -0.6982 0.124 Uiso 1 1 calc R . . C28 C -0.187(2) -0.2866(7) -0.7667(3) 0.151(4) Uani 1 1 d . . . H23A H -0.2072 -0.2885 -0.805 0.227 Uiso 1 1 calc R . . H23B H -0.2686 -0.3446 -0.7496 0.227 Uiso 1 1 calc R . . H23C H -0.0569 -0.3055 -0.7589 0.227 Uiso 1 1 calc R . . C101 C -0.1941(7) -0.2586(4) -0.59603(18) 0.0474(12) Uani 1 1 d . . . H101 H -0.1057 -0.1952 -0.5847 0.057 Uiso 1 1 calc R . . C103 C -0.1233(10) -0.3390(5) -0.6386(2) 0.0762(17) Uani 1 1 d . . . H10A H -0.1633 -0.4226 -0.6376 0.091 Uiso 1 1 calc R . . H10B H 0.0048 -0.3259 -0.6518 0.091 Uiso 1 1 calc R . . N1 N -0.3141(6) -0.3081(3) -0.55320(16) 0.0536(11) Uani 1 1 d . . . H1A H -0.2491 -0.3097 -0.5224 0.08 Uiso 1 1 calc R . . H1B H -0.3492 -0.3826 -0.5619 0.08 Uiso 1 1 calc R . . H1C H -0.4169 -0.2623 -0.5492 0.08 Uiso 1 1 calc R . . N2 N -0.2808(9) 0.3266(4) -0.5937(2) 0.0763(14) Uani 1 1 d . . . N3 N -0.2024(8) -0.0197(4) -0.4776(2) 0.0824(16) Uani 1 1 d . . . N4 N -0.7940(7) 0.0356(5) -0.5817(3) 0.0904(17) Uani 1 1 d . . . O1 O -0.8819(8) 0.0898(7) -0.6110(3) 0.155(3) Uani 1 1 d . . . O2 O -0.8836(9) -0.0322(6) -0.5505(4) 0.178(4) Uani 1 1 d . . . O3 O -0.2195(7) -0.1244(4) -0.47079(19) 0.0953(15) Uani 1 1 d . . . O4 O -0.0956(11) 0.0362(5) -0.4503(3) 0.175(4) Uani 1 1 d . . . O5 O -0.3594(9) 0.3688(4) -0.6321(2) 0.1154(19) Uani 1 1 d . . . O6 O -0.1464(9) 0.3714(4) -0.5723(2) 0.1140(19) Uani 1 1 d . . . O7 O -0.5494(5) -0.1114(3) -0.51877(15) 0.0634(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.055(3) 0.037(2) 0.046(3) 0.0026(19) -0.007(2) -0.009(2) C4 0.040(3) 0.039(3) 0.060(3) 0.004(2) -0.008(2) -0.002(2) C7 0.044(3) 0.043(3) 0.053(3) 0.000(2) 0.010(2) 0.003(2) C8 0.095(4) 0.053(3) 0.039(3) 0.004(2) -0.004(3) -0.026(3) C9 0.069(3) 0.040(2) 0.049(3) 0.002(2) -0.001(3) -0.008(2) C12 0.073(4) 0.052(3) 0.056(3) 0.005(3) -0.015(3) 0.006(3) C15 0.053(3) 0.047(3) 0.065(3) -0.003(2) -0.007(2) -0.009(2) C16 0.050(3) 0.043(3) 0.054(3) 0.001(2) -0.012(2) 0.010(2) C17 0.103(6) 0.104(5) 0.070(4) 0.023(4) -0.022(4) 0.000(5) C18 0.092(5) 0.109(5) 0.073(4) 0.025(4) -0.030(4) -0.040(4) C21 0.138(6) 0.063(3) 0.044(3) 0.007(3) 0.003(4) -0.002(4) C23 0.192(10) 0.151(8) 0.080(5) 0.049(5) 0.025(6) -0.029(8) C24 0.112(6) 0.184(9) 0.108(6) 0.042(6) -0.057(5) -0.043(7) C27 0.177(8) 0.059(4) 0.074(4) 0.022(3) 0.021(5) 0.033(5) C28 0.291(13) 0.111(6) 0.052(4) -0.022(4) 0.002(6) 0.037(8) C101 0.052(3) 0.042(2) 0.048(3) 0.005(2) -0.003(2) -0.012(2) C103 0.098(5) 0.066(3) 0.066(4) 0.010(3) 0.020(3) 0.016(3) N1 0.065(3) 0.042(2) 0.054(2) 0.0123(18) -0.003(2) -0.002(2) N2 0.104(4) 0.053(3) 0.072(3) 0.010(3) -0.002(3) -0.026(3) N3 0.081(4) 0.051(3) 0.115(4) -0.001(3) -0.045(3) -0.002(3) N4 0.059(3) 0.082(4) 0.130(5) 0.046(3) -0.019(3) -0.014(3) O1 0.090(4) 0.224(7) 0.152(5) 0.118(6) -0.048(4) -0.037(4) O2 0.091(4) 0.150(5) 0.292(9) 0.088(6) -0.072(5) -0.048(4) O3 0.106(3) 0.062(3) 0.119(4) 0.023(2) -0.038(3) 0.010(3) O4 0.191(7) 0.084(4) 0.251(8) 0.034(4) -0.155(7) -0.024(4) O5 0.163(5) 0.088(3) 0.095(3) 0.047(3) -0.018(4) -0.041(4) O6 0.134(4) 0.086(3) 0.121(4) 0.013(3) -0.023(3) -0.072(4) O7 0.065(2) 0.0398(19) 0.085(3) 0.0178(18) 0.0117(19) -0.0028(17) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C101 1.481(6) . ? C1 C103 1.499(8) . ? C1 C8 1.502(6) . ? C1 C18 1.522(8) . ? C4 C12 1.359(7) . ? C4 C7 1.425(6) . ? C4 N4 1.441(7) . ? C7 O7 1.252(5) . ? C7 C16 1.422(7) . ? C8 C27 1.543(9) . ? C8 C21 1.558(7) . ? C9 C15 1.350(7) . ? C9 C12 1.368(8) . ? C9 N2 1.471(7) . ? C15 C16 1.376(7) . ? C16 N3 1.451(6) . ? C17 C24 1.494(11) . ? C17 C27 1.503(10) . ? C17 C21 1.509(10) . ? C18 C24 1.552(9) . ? C21 C28 1.517(10) . ? C21 C23 1.530(10) . ? C101 N1 1.463(6) . ? C101 C103 1.469(7) . ? N2 O6 1.192(7) . ? N2 O5 1.197(7) . ? N3 O3 1.182(6) . ? N3 O4 1.186(6) . ? N4 O1 1.127(6) . ? N4 O2 1.250(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C101 C1 C103 59.1(3) . . ? C101 C1 C8 117.4(4) . . ? C103 C1 C8 116.2(5) . . ? C101 C1 C18 118.6(4) . . ? C103 C1 C18 120.4(5) . . ? C8 C1 C18 114.3(5) . . ? C12 C4 C7 123.5(4) . . ? C12 C4 N4 117.5(5) . . ? C7 C4 N4 119.0(5) . . ? O7 C7 C16 123.6(4) . . ? O7 C7 C4 124.2(4) . . ? C16 C7 C4 112.2(4) . . ? C1 C8 C27 107.8(5) . . ? C1 C8 C21 111.1(4) . . ? C27 C8 C21 85.8(5) . . ? C15 C9 C12 120.8(5) . . ? C15 C9 N2 118.9(5) . . ? C12 C9 N2 120.3(5) . . ? C4 C12 C9 119.8(5) . . ? C9 C15 C16 119.2(5) . . ? C15 C16 C7 123.9(4) . . ? C15 C16 N3 116.9(4) . . ? C7 C16 N3 119.2(4) . . ? C24 C17 C27 109.3(6) . . ? C24 C17 C21 112.3(7) . . ? C27 C17 C21 89.0(6) . . ? C1 C18 C24 112.6(6) . . ? C17 C21 C28 120.0(8) . . ? C17 C21 C23 111.9(6) . . ? C28 C21 C23 108.9(7) . . ? C17 C21 C8 85.7(5) . . ? C28 C21 C8 117.2(5) . . ? C23 C21 C8 111.5(6) . . ? C17 C24 C18 112.5(6) . . ? C17 C27 C8 86.4(5) . . ? N1 C101 C103 119.1(4) . . ? N1 C101 C1 119.9(4) . . ? C103 C101 C1 61.1(3) . . ? C101 C103 C1 59.8(3) . . ? O6 N2 O5 123.8(5) . . ? O6 N2 C9 118.5(5) . . ? O5 N2 C9 117.6(5) . . ? O3 N3 O4 119.9(5) . . ? O3 N3 C16 121.3(5) . . ? O4 N3 C16 118.6(5) . . ? O1 N4 O2 116.3(6) . . ? O1 N4 C4 122.6(6) . . ? O2 N4 C4 117.3(6) . . ? #END data_1R,2R,2'R-3 _database_code_depnum_ccdc_archive 'CCDC 780456' #TrackingRef 'deposit_Macchi.cif' _audit_creation_date 2009-07-24T15:40:50-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C12 H18 O2' _chemical_formula_weight 194.26 _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# 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 7.419(2) _cell_length_b 20.487(6) _cell_length_c 28.422(8) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4320(2) _cell_formula_units_Z 16 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6528 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 22.1 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.195 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.825 _exptl_absorpt_correction_T_max 1.0 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_unetI/netI 0.0457 _diffrn_reflns_number 29013 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 26.52 _diffrn_reflns_theta_full 26 _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.946 _reflns_number_total 8298 _reflns_number_gt 6869 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0573P)^2^+1.5238P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 8298 _refine_ls_number_parameters 505 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1205 _refine_ls_wR_factor_gt 0.1129 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.8(10) _refine_diff_density_max 0.324 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.042 #----------------------------------------------------------------------------# # 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' 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 C1 C -0.6607(3) -0.52955(12) -0.83183(9) 0.0268(5) Uani 1 1 d . . . C2 C -0.7748(3) -0.52817(12) -0.78971(9) 0.0269(6) Uani 1 1 d . . . H2 H -0.7353 -0.4989 -0.7644 0.032 Uiso 1 1 calc R . . C3 C -0.9792(3) -0.53871(12) -0.79387(9) 0.0243(5) Uani 1 1 d . . . C4 C -0.8641(3) -0.59117(12) -0.77419(9) 0.0270(6) Uani 1 1 d . . . H4 H -0.8444 -0.6283 -0.7953 0.032 Uiso 1 1 calc R . . C5 C -0.8899(4) -0.60937(13) -0.72260(9) 0.0329(6) Uani 1 1 d . . . H5A H -0.9233 -0.6551 -0.7204 0.039 Uiso 1 1 calc R . . H5B H -0.7768 -0.6036 -0.706 0.039 Uiso 1 1 calc R . . C6 C -1.0343(4) -0.56816(13) -0.69905(9) 0.0304(6) Uani 1 1 d . . . H6 H -1.0569 -0.5784 -0.6659 0.036 Uiso 1 1 calc R . . C7 C -1.0014(4) -0.49575(13) -0.70968(10) 0.0353(7) Uani 1 1 d . . . H7A H -0.8752 -0.4842 -0.713 0.042 Uiso 1 1 calc R . . H7B H -1.0634 -0.4661 -0.6886 0.042 Uiso 1 1 calc R . . C8 C -1.0989(3) -0.50730(12) -0.75652(9) 0.0278(6) Uani 1 1 d . . . H8 H -1.1722 -0.4706 -0.7676 0.033 Uiso 1 1 calc R . . C9 C -1.2066(3) -0.56257(12) -0.73045(8) 0.0269(6) Uani 1 1 d . . . C21 C -0.3350(3) -0.53271(12) -0.93716(8) 0.0244(5) Uani 1 1 d . . . C22 C -0.1841(3) -0.54170(11) -0.96994(8) 0.0241(5) Uani 1 1 d . . . H22 H -0.1539 -0.587 -0.9778 0.029 Uiso 1 1 calc R . . C23 C -0.1399(3) -0.49040(12) -1.00792(8) 0.0242(5) Uani 1 1 d . . . C24 C -0.0250(3) -0.49506(11) -0.96495(8) 0.0219(5) Uani 1 1 d . . . H24 H -0.0415 -0.4599 -0.942 0.026 Uiso 1 1 calc R . . C25 C 0.1679(3) -0.51847(12) -0.97102(9) 0.0261(5) Uani 1 1 d . . . H25A H 0.1846 -0.5583 -0.9531 0.031 Uiso 1 1 calc R . . H25B H 0.2493 -0.4858 -0.9584 0.031 Uiso 1 1 calc R . . C26 C 0.2158(3) -0.53122(12) -1.02226(9) 0.0269(6) Uani 1 1 d . . . H26 H 0.3408 -0.5445 -1.0278 0.032 Uiso 1 1 calc R . . C27 C 0.0724(3) -0.57548(13) -1.04466(9) 0.0321(6) Uani 1 1 d . . . H27A H 0.019 -0.6067 -1.0231 0.038 Uiso 1 1 calc R . . H27B H 0.1104 -0.5963 -1.0737 0.038 Uiso 1 1 calc R . . C28 C -0.0407(3) -0.51262(12) -1.05184(9) 0.0277(6) Uani 1 1 d . . . H28 H -0.1123 -0.5116 -1.0808 0.033 Uiso 1 1 calc R . . C29 C 0.1458(3) -0.47539(12) -1.05469(8) 0.0270(6) Uani 1 1 d . . . C31 C -0.3404(3) -0.82326(12) -0.80361(8) 0.0253(5) Uani 1 1 d . . . C32 C -0.1899(3) -0.83523(11) -0.83599(8) 0.0239(5) Uani 1 1 d . . . H32 H -0.1545 -0.8809 -0.8405 0.029 Uiso 1 1 calc R . . C33 C -0.1532(3) -0.78851(11) -0.87757(8) 0.0216(5) Uani 1 1 d . . . C34 C -0.0367(3) -0.78497(12) -0.83488(9) 0.0252(5) Uani 1 1 d . . . H34 H -0.0586 -0.7471 -0.8146 0.03 Uiso 1 1 calc R . . C35 C 0.1602(3) -0.80492(13) -0.83932(9) 0.0302(6) Uani 1 1 d . . . H35A H 0.1839 -0.8414 -0.8185 0.036 Uiso 1 1 calc R . . H35B H 0.2363 -0.7688 -0.8296 0.036 Uiso 1 1 calc R . . C36 C 0.2076(3) -0.82436(12) -0.88970(9) 0.0277(6) Uani 1 1 d . . . H36 H 0.3343 -0.8359 -0.8948 0.033 Uiso 1 1 calc R . . C37 C 0.0715(3) -0.87433(12) -0.90794(9) 0.0278(6) Uani 1 1 d . . . H37A H 0.0237 -0.9032 -0.8839 0.033 Uiso 1 1 calc R . . H37B H 0.112 -0.8986 -0.9353 0.033 Uiso 1 1 calc R . . C38 C -0.0512(3) -0.81543(11) -0.91961(9) 0.0237(5) Uani 1 1 d . . . H38 H -0.1231 -0.8202 -0.9483 0.028 Uiso 1 1 calc R . . C39 C 0.1284(3) -0.77521(12) -0.92577(8) 0.0262(6) Uani 1 1 d . . . C41 C -0.3245(3) -0.29023(13) -0.79729(9) 0.0283(6) Uani 1 1 d . . . C42 C -0.2071(3) -0.27137(12) -0.83670(9) 0.0264(5) Uani 1 1 d . . . H42 H -0.2325 -0.2284 -0.8504 0.032 Uiso 1 1 calc R . . C43 C -0.0087(3) -0.29156(12) -0.83722(9) 0.0250(5) Uani 1 1 d . . . C44 C -0.1370(3) -0.32188(12) -0.87103(9) 0.0287(6) Uani 1 1 d . . . H44 H -0.1708 -0.3671 -0.8641 0.034 Uiso 1 1 calc R . . C45 C -0.1115(4) -0.30595(14) -0.92318(9) 0.0379(7) Uani 1 1 d . . . H45A H -0.094 -0.3462 -0.9405 0.045 Uiso 1 1 calc R . . H45B H -0.22 -0.2852 -0.935 0.045 Uiso 1 1 calc R . . C46 C 0.0488(4) -0.26102(14) -0.93174(9) 0.0345(6) Uani 1 1 d . . . H46 H 0.0719 -0.2505 -0.9648 0.041 Uiso 1 1 calc R . . C47 C 0.0356(4) -0.20148(13) -0.89866(10) 0.0367(7) Uani 1 1 d . . . H47A H -0.0867 -0.1883 -0.8913 0.044 Uiso 1 1 calc R . . H47B H 0.1087 -0.1645 -0.9082 0.044 Uiso 1 1 calc R . . C48 C 0.1241(3) -0.24552(12) -0.86116(9) 0.0271(6) Uani 1 1 d . . . H48 H 0.2069 -0.223 -0.8398 0.032 Uiso 1 1 calc R . . C49 C 0.2178(4) -0.28233(13) -0.90315(9) 0.0308(6) Uani 1 1 d . . . C91 C -1.2691(4) -0.62312(13) -0.75657(10) 0.0360(7) Uani 1 1 d . . . H91A H -1.1699 -0.6413 -0.7739 0.054 Uiso 1 1 calc R . . H91B H -1.364 -0.6116 -0.778 0.054 Uiso 1 1 calc R . . H91C H -1.3128 -0.6547 -0.7344 0.054 Uiso 1 1 calc R . . C92 C -1.3660(4) -0.53588(16) -0.70269(11) 0.0465(8) Uani 1 1 d . . . H92A H -1.3296 -0.4973 -0.686 0.07 Uiso 1 1 calc R . . H92B H -1.4065 -0.5682 -0.6806 0.07 Uiso 1 1 calc R . . H92C H -1.4623 -0.5253 -0.7239 0.07 Uiso 1 1 calc R . . C231 C -0.2700(3) -0.43538(13) -1.01601(10) 0.0330(6) Uani 1 1 d . . . H23A H -0.3311 -0.4418 -1.0454 0.049 Uiso 1 1 calc R . . H23B H -0.2054 -0.3948 -1.0168 0.049 Uiso 1 1 calc R . . H23C H -0.3567 -0.4343 -0.9909 0.049 Uiso 1 1 calc R . . C291 C 0.2266(4) -0.47868(15) -1.10422(9) 0.0417(7) Uani 1 1 d . . . H29A H 0.1768 -0.4443 -1.1232 0.063 Uiso 1 1 calc R . . H29B H 0.1985 -0.5201 -1.1182 0.063 Uiso 1 1 calc R . . H29C H 0.355 -0.4736 -1.1024 0.063 Uiso 1 1 calc R . . C292 C 0.1653(4) -0.40556(12) -1.03690(10) 0.0326(6) Uani 1 1 d . . . H29D H 0.115 -0.376 -1.0596 0.049 Uiso 1 1 calc R . . H29E H 0.2906 -0.3957 -1.0324 0.049 Uiso 1 1 calc R . . H29F H 0.1025 -0.401 -1.0075 0.049 Uiso 1 1 calc R . . C331 C -0.2884(4) -0.73632(12) -0.88969(9) 0.0309(6) Uani 1 1 d . . . H33A H -0.3466 -0.7215 -0.8615 0.046 Uiso 1 1 calc R . . H33B H -0.3771 -0.7539 -0.9108 0.046 Uiso 1 1 calc R . . H33C H -0.2279 -0.7004 -0.9045 0.046 Uiso 1 1 calc R . . C391 C 0.1355(4) -0.70284(12) -0.91380(10) 0.0354(6) Uani 1 1 d . . . H39A H 0.0891 -0.6961 -0.8826 0.053 Uiso 1 1 calc R . . H39B H 0.0638 -0.6788 -0.936 0.053 Uiso 1 1 calc R . . H39C H 0.258 -0.6879 -0.9153 0.053 Uiso 1 1 calc R . . C392 C 0.2069(4) -0.78400(14) -0.97503(9) 0.0366(7) Uani 1 1 d . . . H39D H 0.2073 -0.8295 -0.983 0.055 Uiso 1 1 calc R . . H39E H 0.328 -0.7676 -0.9757 0.055 Uiso 1 1 calc R . . H39F H 0.1347 -0.7604 -0.9973 0.055 Uiso 1 1 calc R . . C431 C 0.0675(4) -0.32848(15) -0.79592(10) 0.0386(7) Uani 1 1 d . . . H43A H 0.1491 -0.3008 -0.7789 0.058 Uiso 1 1 calc R . . H43B H 0.131 -0.3663 -0.807 0.058 Uiso 1 1 calc R . . H43C H -0.0289 -0.3418 -0.7755 0.058 Uiso 1 1 calc R . . C491 C 0.3875(4) -0.24761(16) -0.91946(11) 0.0457(8) Uani 1 1 d . . . H49A H 0.4884 -0.2624 -0.9012 0.069 Uiso 1 1 calc R . . H49B H 0.3731 -0.2014 -0.9154 0.069 Uiso 1 1 calc R . . H49C H 0.4083 -0.2571 -0.9521 0.069 Uiso 1 1 calc R . . C492 C 0.2606(4) -0.35449(13) -0.89919(10) 0.0397(7) Uani 1 1 d . . . H49D H 0.3672 -0.3602 -0.8805 0.06 Uiso 1 1 calc R . . H49E H 0.2802 -0.3722 -0.93 0.06 Uiso 1 1 calc R . . H49F H 0.1614 -0.3767 -0.8845 0.06 Uiso 1 1 calc R . . O11 O -0.6592(3) -0.57346(9) -0.86070(6) 0.0375(5) Uani 1 1 d . . . O12 O -0.5580(2) -0.47714(9) -0.83563(7) 0.0368(5) Uani 1 1 d . . . H12 H -0.4971 -0.4797 -0.8596 0.055 Uiso 1 1 calc R . . O21 O -0.3696(2) -0.48169(8) -0.91669(6) 0.0296(4) Uani 1 1 d . . . O22 O -0.4283(2) -0.58681(8) -0.93106(6) 0.0318(4) Uani 1 1 d . . . H22A H -0.511 -0.58 -0.9125 0.048 Uiso 1 1 calc R . . O31 O -0.3886(2) -0.76911(8) -0.79100(6) 0.0323(4) Uani 1 1 d . . . O32 O -0.4160(2) -0.87760(8) -0.78756(7) 0.0340(4) Uani 1 1 d . . . H32A H -0.4977 -0.8682 -0.7694 0.051 Uiso 1 1 calc R . . O41 O -0.4065(3) -0.23894(9) -0.77937(7) 0.0421(5) Uani 1 1 d . . . H41 H -0.4717 -0.2505 -0.7576 0.063 Uiso 1 1 calc R . . O42 O -0.3447(3) -0.34537(9) -0.78200(7) 0.0382(5) Uani 1 1 d . . . C131 C -1.0631(4) -0.54306(15) -0.84197(9) 0.0364(7) Uani 1 1 d . . . H13A H -1.1334 -0.5046 -0.8478 0.055 Uiso 1 1 calc R . . H13B H -1.1396 -0.5808 -0.8435 0.055 Uiso 1 1 calc R . . H13C H -0.97 -0.5466 -0.8653 0.055 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 0.0228(13) 0.0309(13) 0.0266(13) 0.0022(11) -0.0008(11) 0.0015(11) C2 0.0275(13) 0.0298(13) 0.0233(13) -0.0028(11) -0.0024(10) -0.0024(11) C3 0.0233(13) 0.0285(13) 0.0210(13) 0.0000(10) 0.0015(10) -0.0025(10) C4 0.0272(14) 0.0287(13) 0.0251(13) 0.0002(10) 0.0011(11) 0.0001(11) C5 0.0311(15) 0.0376(15) 0.0299(15) 0.0082(12) -0.0054(12) 0.0011(12) C6 0.0292(14) 0.0420(15) 0.0201(13) 0.0012(12) 0.0004(11) -0.0047(12) C7 0.0319(15) 0.0415(16) 0.0324(15) -0.0161(13) 0.0063(12) -0.0075(12) C8 0.0238(13) 0.0273(13) 0.0322(14) -0.0003(11) -0.0008(11) 0.0045(11) C9 0.0234(13) 0.0321(13) 0.0251(13) -0.0027(11) 0.0009(10) -0.0032(11) C21 0.0215(12) 0.0277(13) 0.0239(13) 0.0066(11) -0.0021(10) -0.0006(11) C22 0.0201(12) 0.0245(12) 0.0275(13) 0.0023(10) 0.0015(10) -0.0001(10) C23 0.0160(12) 0.0308(13) 0.0257(13) 0.0035(10) -0.0011(10) 0.0002(10) C24 0.0214(12) 0.0233(12) 0.0208(13) 0.0045(10) -0.0012(10) -0.0017(10) C25 0.0189(13) 0.0314(13) 0.0281(14) 0.0056(11) -0.0020(10) 0.0001(11) C26 0.0186(12) 0.0320(13) 0.0303(14) 0.0020(11) 0.0042(10) 0.0027(11) C27 0.0293(14) 0.0351(15) 0.0317(15) -0.0097(12) 0.0074(12) -0.0011(12) C28 0.0252(13) 0.0390(15) 0.0190(13) 0.0010(11) -0.0016(10) -0.0023(12) C29 0.0205(12) 0.0374(14) 0.0233(13) 0.0041(11) 0.0027(10) 0.0015(12) C31 0.0222(13) 0.0300(13) 0.0238(13) 0.0015(11) -0.0004(10) 0.0010(11) C32 0.0237(13) 0.0243(12) 0.0238(13) 0.0029(10) -0.0004(11) 0.0046(10) C33 0.0216(12) 0.0223(11) 0.0209(12) -0.0007(10) 0.0020(10) -0.0030(10) C34 0.0240(13) 0.0246(12) 0.0271(13) -0.0025(11) -0.0006(11) -0.0017(10) C35 0.0230(13) 0.0399(15) 0.0278(14) 0.0001(12) -0.0039(11) -0.0014(12) C36 0.0168(12) 0.0334(13) 0.0329(14) 0.0030(11) 0.0022(11) 0.0024(11) C37 0.0282(14) 0.0246(12) 0.0306(14) 0.0002(11) 0.0099(11) 0.0041(11) C38 0.0213(12) 0.0265(12) 0.0234(13) -0.0005(10) -0.0027(10) -0.0001(10) C39 0.0231(13) 0.0289(13) 0.0266(13) 0.0019(10) 0.0050(11) -0.0018(11) C41 0.0213(13) 0.0337(14) 0.0299(14) -0.0007(12) 0.0019(11) -0.0008(11) C42 0.0247(13) 0.0258(12) 0.0287(13) -0.0009(11) 0.0021(11) 0.0006(10) C43 0.0232(13) 0.0269(12) 0.0248(13) -0.0001(11) 0.0026(11) 0.0006(10) C44 0.0231(13) 0.0302(13) 0.0328(14) -0.0060(11) 0.0012(11) -0.0009(11) C45 0.0267(15) 0.0576(18) 0.0293(15) -0.0139(13) -0.0037(12) 0.0060(13) C46 0.0302(15) 0.0526(17) 0.0208(13) 0.0049(12) 0.0010(11) 0.0092(13) C47 0.0353(16) 0.0360(15) 0.0388(16) 0.0117(12) 0.0126(13) 0.0048(12) C48 0.0263(13) 0.0282(13) 0.0267(13) -0.0013(11) 0.0015(11) -0.0058(11) C49 0.0254(13) 0.0408(15) 0.0262(14) 0.0044(12) 0.0023(11) 0.0043(12) C91 0.0324(15) 0.0414(15) 0.0343(15) -0.0014(13) -0.0004(12) -0.0130(13) C92 0.0335(16) 0.0592(19) 0.0468(18) -0.0036(15) 0.0101(14) 0.0016(15) C231 0.0235(14) 0.0413(15) 0.0341(15) 0.0122(12) -0.0006(11) 0.0018(12) C291 0.0314(15) 0.064(2) 0.0294(16) 0.0091(14) 0.0058(12) 0.0017(14) C292 0.0247(14) 0.0344(14) 0.0387(16) 0.0116(12) 0.0061(12) 0.0015(12) C331 0.0298(14) 0.0333(14) 0.0296(14) 0.0056(11) 0.0009(12) 0.0065(12) C391 0.0339(15) 0.0306(14) 0.0417(16) 0.0006(12) 0.0086(13) -0.0044(12) C392 0.0316(15) 0.0442(16) 0.0341(15) 0.0060(13) 0.0095(12) 0.0038(13) C431 0.0328(15) 0.0499(17) 0.0332(16) 0.0129(14) 0.0001(13) 0.0042(14) C491 0.0323(16) 0.061(2) 0.0435(17) 0.0115(15) 0.0080(14) 0.0032(14) C492 0.0364(16) 0.0445(16) 0.0381(16) -0.0030(13) 0.0042(13) 0.0127(13) O11 0.0389(11) 0.0408(11) 0.0326(10) -0.0051(9) 0.0114(9) -0.0089(9) O12 0.0387(11) 0.0344(10) 0.0373(11) -0.0015(9) 0.0147(9) -0.0059(9) O21 0.0292(10) 0.0277(9) 0.0321(10) 0.0034(8) 0.0081(8) 0.0009(8) O22 0.0260(9) 0.0323(10) 0.0372(11) -0.0001(8) 0.0101(8) -0.0061(8) O31 0.0328(10) 0.0284(9) 0.0357(10) -0.0011(8) 0.0126(9) 0.0019(8) O32 0.0311(10) 0.0290(10) 0.0418(11) -0.0008(8) 0.0138(9) -0.0035(8) O41 0.0456(12) 0.0320(10) 0.0485(12) 0.0069(9) 0.0275(10) 0.0058(9) O42 0.0380(11) 0.0301(10) 0.0464(12) 0.0023(9) 0.0175(9) -0.0024(9) C131 0.0312(15) 0.0517(18) 0.0263(15) 0.0046(13) -0.0035(12) -0.0025(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O11 1.218(3) . ? C1 O12 1.321(3) . ? C1 C2 1.467(4) . ? C2 C4 1.516(3) . ? C2 C3 1.536(4) . ? C3 C4 1.483(3) . ? C3 C131 1.505(3) . ? C3 C8 1.526(3) . ? C4 C5 1.525(3) . ? C5 C6 1.519(4) . ? C6 C7 1.534(4) . ? C6 C9 1.563(4) . ? C7 C8 1.534(4) . ? C8 C9 1.572(3) . ? C9 C91 1.518(4) . ? C9 C92 1.523(4) . ? C21 O21 1.224(3) . ? C21 O22 1.319(3) . ? C21 C22 1.468(3) . ? C22 C24 1.525(3) . ? C22 C23 1.542(3) . ? C23 C24 1.492(3) . ? C23 C231 1.502(3) . ? C23 C28 1.519(3) . ? C24 C25 1.519(3) . ? C25 C26 1.521(3) . ? C26 C27 1.536(4) . ? C26 C29 1.558(3) . ? C27 C28 1.550(4) . ? C28 C29 1.582(4) . ? C29 C292 1.524(4) . ? C29 C291 1.531(3) . ? C31 O31 1.219(3) . ? C31 O32 1.328(3) . ? C31 C32 1.467(3) . ? C32 C34 1.534(3) . ? C32 C33 1.545(3) . ? C33 C34 1.492(3) . ? C33 C331 1.506(3) . ? C33 C38 1.518(3) . ? C34 C35 1.522(4) . ? C35 C36 1.527(4) . ? C36 C37 1.528(4) . ? C36 C39 1.552(3) . ? C37 C38 1.547(3) . ? C38 C39 1.576(3) . ? C39 C391 1.522(3) . ? C39 C392 1.527(4) . ? C41 O42 1.220(3) . ? C41 O41 1.317(3) . ? C41 C42 1.470(3) . ? C42 C44 1.514(3) . ? C42 C43 1.529(4) . ? C43 C44 1.488(3) . ? C43 C431 1.507(4) . ? C43 C48 1.524(3) . ? C44 C45 1.529(4) . ? C45 C46 1.524(4) . ? C46 C47 1.543(4) . ? C46 C49 1.556(4) . ? C47 C48 1.543(4) . ? C48 C49 1.573(4) . ? C49 C492 1.516(4) . ? C49 C491 1.519(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O11 C1 O12 122.7(2) . . ? O11 C1 C2 124.7(2) . . ? O12 C1 C2 112.6(2) . . ? C1 C2 C4 118.2(2) . . ? C1 C2 C3 120.3(2) . . ? C4 C2 C3 58.11(16) . . ? C4 C3 C131 122.6(2) . . ? C4 C3 C8 112.2(2) . . ? C131 C3 C8 114.6(2) . . ? C4 C3 C2 60.26(17) . . ? C131 C3 C2 119.1(2) . . ? C8 C3 C2 117.5(2) . . ? C3 C4 C2 61.63(17) . . ? C3 C4 C5 117.9(2) . . ? C2 C4 C5 122.9(2) . . ? C6 C5 C4 112.1(2) . . ? C5 C6 C7 109.8(2) . . ? C5 C6 C9 111.5(2) . . ? C7 C6 C9 87.0(2) . . ? C6 C7 C8 86.93(19) . . ? C3 C8 C7 113.2(2) . . ? C3 C8 C9 108.66(19) . . ? C7 C8 C9 86.67(19) . . ? C91 C9 C92 108.1(2) . . ? C91 C9 C6 118.0(2) . . ? C92 C9 C6 111.4(2) . . ? C91 C9 C8 120.9(2) . . ? C92 C9 C8 112.4(2) . . ? C6 C9 C8 84.62(18) . . ? O21 C21 O22 123.0(2) . . ? O21 C21 C22 124.7(2) . . ? O22 C21 C22 112.2(2) . . ? C21 C22 C24 116.9(2) . . ? C21 C22 C23 121.4(2) . . ? C24 C22 C23 58.22(15) . . ? C24 C23 C231 122.7(2) . . ? C24 C23 C28 112.1(2) . . ? C231 C23 C28 114.2(2) . . ? C24 C23 C22 60.33(15) . . ? C231 C23 C22 118.8(2) . . ? C28 C23 C22 118.3(2) . . ? C23 C24 C25 117.7(2) . . ? C23 C24 C22 61.45(16) . . ? C25 C24 C22 121.4(2) . . ? C24 C25 C26 112.5(2) . . ? C25 C26 C27 109.7(2) . . ? C25 C26 C29 111.3(2) . . ? C27 C26 C29 87.56(19) . . ? C26 C27 C28 86.49(19) . . ? C23 C28 C27 113.8(2) . . ? C23 C28 C29 108.8(2) . . ? C27 C28 C29 86.24(18) . . ? C292 C29 C291 108.0(2) . . ? C292 C29 C26 117.5(2) . . ? C291 C29 C26 112.4(2) . . ? C292 C29 C28 121.2(2) . . ? C291 C29 C28 111.6(2) . . ? C26 C29 C28 84.65(18) . . ? O31 C31 O32 122.5(2) . . ? O31 C31 C32 124.0(2) . . ? O32 C31 C32 113.4(2) . . ? C31 C32 C34 116.0(2) . . ? C31 C32 C33 120.7(2) . . ? C34 C32 C33 57.95(15) . . ? C34 C33 C331 122.5(2) . . ? C34 C33 C38 111.6(2) . . ? C331 C33 C38 114.2(2) . . ? C34 C33 C32 60.66(16) . . ? C331 C33 C32 119.8(2) . . ? C38 C33 C32 117.70(19) . . ? C33 C34 C35 118.4(2) . . ? C33 C34 C32 61.39(15) . . ? C35 C34 C32 121.9(2) . . ? C34 C35 C36 111.6(2) . . ? C35 C36 C37 109.9(2) . . ? C35 C36 C39 111.3(2) . . ? C37 C36 C39 87.75(18) . . ? C36 C37 C38 86.49(18) . . ? C33 C38 C37 114.1(2) . . ? C33 C38 C39 108.59(19) . . ? C37 C38 C39 86.23(18) . . ? C391 C39 C392 107.9(2) . . ? C391 C39 C36 118.1(2) . . ? C392 C39 C36 112.6(2) . . ? C391 C39 C38 120.9(2) . . ? C392 C39 C38 111.2(2) . . ? C36 C39 C38 84.69(17) . . ? O42 C41 O41 123.0(2) . . ? O42 C41 C42 126.0(2) . . ? O41 C41 C42 111.0(2) . . ? C41 C42 C44 121.0(2) . . ? C41 C42 C43 120.4(2) . . ? C44 C42 C43 58.56(16) . . ? C44 C43 C431 122.3(2) . . ? C44 C43 C48 112.5(2) . . ? C431 C43 C48 114.6(2) . . ? C44 C43 C42 60.24(17) . . ? C431 C43 C42 119.3(2) . . ? C48 C43 C42 117.3(2) . . ? C43 C44 C42 61.20(17) . . ? C43 C44 C45 117.2(2) . . ? C42 C44 C45 121.4(2) . . ? C46 C45 C44 112.3(2) . . ? C45 C46 C47 109.3(2) . . ? C45 C46 C49 112.1(2) . . ? C47 C46 C49 87.4(2) . . ? C46 C47 C48 86.07(19) . . ? C43 C48 C47 113.3(2) . . ? C43 C48 C49 109.1(2) . . ? C47 C48 C49 86.80(18) . . ? C492 C49 C491 107.8(2) . . ? C492 C49 C46 118.8(2) . . ? C491 C49 C46 112.1(2) . . ? C492 C49 C48 120.2(2) . . ? C491 C49 C48 111.9(2) . . ? C46 C49 C48 84.61(19) . . ? #END data_1R,2R,2'R-7 _database_code_depnum_ccdc_archive 'CCDC 780457' #TrackingRef 'deposit_Macchi.cif' _audit_creation_date 2009-07-24T16:57:30-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C17 H22 N4 O7' _chemical_formula_weight 394.39 _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 14.079(4) _cell_length_b 12.207(3) _cell_length_c 22.502(6) _cell_angle_alpha 90 _cell_angle_beta 102.181(7) _cell_angle_gamma 90 _cell_volume 3780.2(17) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2756 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 19.4 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.876 _exptl_absorpt_correction_T_max 1.0 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_unetI/netI 0.0866 _diffrn_reflns_number 17534 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 22.11 _diffrn_reflns_theta_full 22.11 _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _reflns_number_total 8969 _reflns_number_gt 6147 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0972P)^2^+1.7489P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 8969 _refine_ls_number_parameters 986 _refine_ls_number_restraints 35 _refine_ls_R_factor_all 0.107 _refine_ls_R_factor_gt 0.0685 _refine_ls_wR_factor_ref 0.1981 _refine_ls_wR_factor_gt 0.1712 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -3(2) _refine_diff_density_max 0.488 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.054 #----------------------------------------------------------------------------# # 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 C51 C 0.8208(6) 0.2797(6) 0.8706(4) 0.057(2) Uani 1 1 d . . . H51 H 0.8343 0.201 0.8749 0.068 Uiso 1 1 calc R . . C52 C 0.7344(5) 0.3171(6) 0.8951(3) 0.0479(19) Uani 1 1 d . . . H52A H 0.6963 0.3778 0.8747 0.057 Uiso 1 1 calc R . . H52B H 0.6974 0.2619 0.9115 0.057 Uiso 1 1 calc R . . C53 C 0.8356(5) 0.3407(6) 0.9292(3) 0.043(2) Uani 1 1 d . . . C54 C 0.8721(5) 0.4571(6) 0.9313(3) 0.0388(19) Uani 1 1 d . . . H54 H 0.8557 0.4961 0.8925 0.047 Uiso 1 1 calc R . . C55 C 0.9802(5) 0.4613(8) 0.9624(3) 0.061(2) Uani 1 1 d . . . H55A H 1.0136 0.5271 0.9539 0.073 Uiso 1 1 calc R . . H55B H 1.0165 0.3958 0.957 0.073 Uiso 1 1 calc R . . C56 C 0.9434(6) 0.4649(10) 1.0238(4) 0.072(3) Uani 1 1 d . . . H56 H 0.9829 0.5098 1.0558 0.086 Uiso 1 1 calc R . . C57 C 0.9226(9) 0.3511(11) 1.0429(4) 0.105(4) Uani 1 1 d . . . H57A H 0.8756 0.3546 1.0688 0.126 Uiso 1 1 calc R . . H57B H 0.9819 0.3191 1.0664 0.126 Uiso 1 1 calc R . . C58 C 0.8823(7) 0.2769(7) 0.9872(4) 0.079(3) Uani 1 1 d . . . H58A H 0.935 0.2326 0.9786 0.095 Uiso 1 1 calc R . . H58B H 0.8343 0.2277 0.9976 0.095 Uiso 1 1 calc R . . C59 C 0.8492(6) 0.5225(8) 0.9872(3) 0.058(2) Uani 1 1 d . . . C591 C 0.7558(6) 0.4986(8) 1.0056(4) 0.072(3) Uani 1 1 d . . . H59A H 0.7502 0.5439 1.0395 0.107 Uiso 1 1 calc R . . H59B H 0.7543 0.4229 1.0169 0.107 Uiso 1 1 calc R . . H59C H 0.7027 0.5135 0.9721 0.107 Uiso 1 1 calc R . . C592 C 0.8613(6) 0.6446(7) 0.9794(4) 0.067(2) Uani 1 1 d . . . H59D H 0.9216 0.6583 0.9671 0.1 Uiso 1 1 calc R . . H59E H 0.8617 0.6811 1.0172 0.1 Uiso 1 1 calc R . . H59F H 0.8084 0.6717 0.9488 0.1 Uiso 1 1 calc R . . N61 N 0.9187(15) 0.9897(17) 0.2909(8) 0.072(8) Uiso 0.5 1 d PD A 1 H61A H 0.9115 0.9508 0.2568 0.107 Uiso 0.5 1 calc PR A 1 H61B H 0.9777 1.0196 0.2993 0.107 Uiso 0.5 1 calc PR A 1 H61C H 0.874 1.0424 0.2862 0.107 Uiso 0.5 1 calc PR A 1 C61 C 0.9062(11) 0.9131(13) 0.3442(6) 0.046(3) Uiso 0.5 1 d PD A 1 H61 H 0.928 0.8371 0.3424 0.055 Uiso 0.5 1 calc PR A 1 C62 C 0.8167(10) 0.9305(14) 0.3685(7) 0.066(3) Uiso 0.5 1 d PD A 1 H62A H 0.7735 0.9899 0.3517 0.079 Uiso 0.5 1 calc PR A 1 H62B H 0.7852 0.8669 0.3815 0.079 Uiso 0.5 1 calc PR A 1 C63 C 0.9156(11) 0.9587(12) 0.4023(6) 0.048(3) Uiso 0.5 1 d PD A 1 C64 C 0.9299(13) 1.0822(14) 0.4166(7) 0.079(4) Uiso 0.5 1 d PD A 1 H64 H 0.9066 1.133 0.383 0.095 Uiso 0.5 1 calc PR A 1 C65 C 1.0443(14) 1.093(2) 0.4511(9) 0.111(6) Uiso 0.5 1 d PD A 1 H65A H 1.0714 1.1661 0.4506 0.133 Uiso 0.5 1 calc PR A 1 H65B H 1.0868 1.0377 0.4399 0.133 Uiso 0.5 1 calc PR A 1 C66 C 1.0022(14) 1.0643(19) 0.5121(9) 0.092(5) Uiso 0.5 1 d PD A 1 H66 H 1.0345 1.1008 0.5497 0.111 Uiso 0.5 1 calc PR A 1 C67 C 0.9933(19) 0.9413(19) 0.5153(10) 0.126(6) Uiso 0.5 1 d PD A 1 H67A H 1.0561 0.9105 0.5338 0.152 Uiso 0.5 1 calc PR A 1 H67B H 0.9481 0.9229 0.5409 0.152 Uiso 0.5 1 calc PR A 1 C68 C 0.9607(15) 0.8943(16) 0.4571(8) 0.097(5) Uiso 0.5 1 d PD A 1 H68A H 0.9141 0.838 0.4617 0.116 Uiso 0.5 1 calc PR A 1 H68B H 1.0161 0.8568 0.4473 0.116 Uiso 0.5 1 calc PR A 1 C69 C 0.9006(14) 1.1101(16) 0.4811(7) 0.074(4) Uiso 0.5 1 d PD A 1 C691 C 0.8063(14) 1.0627(19) 0.4876(11) 0.097(5) Uiso 0.5 1 d PD A 1 H69A H 0.7674 1.1187 0.5007 0.145 Uiso 0.5 1 calc PR A 1 H69B H 0.8176 1.0049 0.5172 0.145 Uiso 0.5 1 calc PR A 1 H69C H 0.7728 1.0339 0.4492 0.145 Uiso 0.5 1 calc PR A 1 C692 C 0.8894(19) 1.2369(17) 0.4844(12) 0.132(7) Uiso 0.5 1 d PD A 1 H69D H 0.9526 1.2701 0.4947 0.198 Uiso 0.5 1 calc PR A 1 H69E H 0.8534 1.2547 0.5149 0.198 Uiso 0.5 1 calc PR A 1 H69F H 0.8554 1.2639 0.4457 0.198 Uiso 0.5 1 calc PR A 1 C71 C 0.6168(6) 0.4567(6) 0.6679(3) 0.058(2) Uani 1 1 d . . . H71 H 0.68 0.4935 0.6785 0.069 Uiso 1 1 calc R . . C72 C 0.5396(8) 0.5188(7) 0.6258(4) 0.078(3) Uani 1 1 d . . . H72A H 0.5558 0.591 0.6129 0.093 Uiso 1 1 calc R . . H72B H 0.4732 0.5107 0.6308 0.093 Uiso 1 1 calc R . . C73 C 0.5865(8) 0.4215(7) 0.6026(4) 0.070(3) Uani 1 1 d . . . C74 C 0.5336(7) 0.3218(7) 0.5851(4) 0.073(3) Uani 1 1 d . . . H74 H 0.4923 0.2973 0.6126 0.087 Uiso 1 1 calc R . . C75 C 0.6033(8) 0.2306(7) 0.5671(4) 0.084(3) Uani 1 1 d . . . H75A H 0.6706 0.2358 0.5885 0.1 Uiso 1 1 calc R . . H75B H 0.5789 0.1563 0.5668 0.1 Uiso 1 1 calc R . . C76 C 0.5802(11) 0.2890(10) 0.5045(4) 0.100(4) Uani 1 1 d . . . H76 H 0.577 0.2387 0.4702 0.12 Uiso 1 1 calc R . . C77 C 0.6479(11) 0.3850(11) 0.5031(5) 0.122(4) Uani 1 1 d . . . H77A H 0.6177 0.4372 0.4724 0.147 Uiso 1 1 calc R . . H77B H 0.7077 0.3596 0.4929 0.147 Uiso 1 1 calc R . . C78 C 0.6707(8) 0.4410(10) 0.5666(4) 0.103(4) Uani 1 1 d . . . H78A H 0.679 0.5191 0.5614 0.123 Uiso 1 1 calc R . . H78B H 0.7312 0.4122 0.5902 0.123 Uiso 1 1 calc R . . C79 C 0.4817(10) 0.3235(8) 0.5135(5) 0.102(4) Uani 1 1 d . . . C791 C 0.4429(10) 0.4339(9) 0.4888(5) 0.137(6) Uani 1 1 d . . . H79A H 0.4948 0.4864 0.4954 0.206 Uiso 1 1 calc R . . H79B H 0.3932 0.4575 0.5092 0.206 Uiso 1 1 calc R . . H79C H 0.4161 0.4277 0.446 0.206 Uiso 1 1 calc R . . C792 C 0.4043(12) 0.2390(12) 0.5015(6) 0.184(8) Uani 1 1 d . . . H79D H 0.3446 0.2699 0.5079 0.276 Uiso 1 1 calc R . . H79E H 0.4226 0.1783 0.5286 0.276 Uiso 1 1 calc R . . H79F H 0.3957 0.2142 0.4602 0.276 Uiso 1 1 calc R . . C81 C 0.7135(7) 0.0928(8) 0.1382(4) 0.067(3) Uani 1 1 d . . . H81 H 0.7825 0.1106 0.1523 0.081 Uiso 1 1 calc R . . C82 C 0.6686(8) 0.1519(9) 0.0864(5) 0.096(3) Uani 1 1 d . . . H82A H 0.7072 0.2068 0.0711 0.116 Uiso 1 1 calc R . . H82B H 0.6007 0.1712 0.0825 0.116 Uiso 1 1 calc R . . C83 C 0.6916(7) 0.0364(7) 0.0781(4) 0.060(2) Uani 1 1 d . . . C84 C 0.6171(6) -0.0506(8) 0.0648(4) 0.064(3) Uani 1 1 d . . . H84 H 0.5673 -0.049 0.0893 0.077 Uiso 1 1 calc R . . C85 C 0.6576(9) -0.1601(9) 0.0562(5) 0.100(4) Uani 1 1 d . . . H85A H 0.6133 -0.2202 0.0582 0.12 Uiso 1 1 calc R . . H85B H 0.7209 -0.1737 0.0821 0.12 Uiso 1 1 calc R . . C86 C 0.6612(8) -0.1247(8) -0.0084(5) 0.079(3) Uani 1 1 d . . . H86 H 0.6492 -0.1843 -0.0382 0.094 Uiso 1 1 calc R . . C87 C 0.7515(6) -0.0649(8) -0.0072(4) 0.069(3) Uani 1 1 d . . . H87A H 0.7431 -0.0172 -0.0424 0.083 Uiso 1 1 calc R . . H87B H 0.8029 -0.1165 -0.0096 0.083 Uiso 1 1 calc R . . C88 C 0.7819(6) 0.0058(8) 0.0524(4) 0.081(3) Uani 1 1 d . . . H88A H 0.8273 -0.0354 0.0827 0.098 Uiso 1 1 calc R . . H88B H 0.8142 0.0721 0.0435 0.098 Uiso 1 1 calc R . . C89 C 0.5765(7) -0.0550(9) -0.0085(5) 0.073(3) Uani 1 1 d . . . C891 C 0.5688(7) 0.0520(9) -0.0430(4) 0.083(3) Uani 1 1 d . . . H89A H 0.5095 0.0884 -0.04 0.124 Uiso 1 1 calc R . . H89B H 0.5689 0.0378 -0.0849 0.124 Uiso 1 1 calc R . . H89C H 0.6231 0.0979 -0.0259 0.124 Uiso 1 1 calc R . . C892 C 0.4844(9) -0.1102(13) -0.0252(5) 0.139(5) Uani 1 1 d . . . H89D H 0.4328 -0.0577 -0.0282 0.208 Uiso 1 1 calc R . . H89E H 0.4791 -0.1637 0.0052 0.208 Uiso 1 1 calc R . . H89F H 0.4799 -0.146 -0.0637 0.208 Uiso 1 1 calc R . . N91 N 0.9110(10) 1.0098(12) 0.2786(5) 0.018(4) Uiso 0.5 1 d PD B 2 H91A H 0.9271 0.982 0.2455 0.027 Uiso 0.5 1 calc PR B 2 H91B H 0.9179 1.0823 0.2787 0.027 Uiso 0.5 1 calc PR B 2 H91C H 0.8495 0.9932 0.2787 0.027 Uiso 0.5 1 calc PR B 2 C91 C 0.9776(10) 0.9614(11) 0.3357(5) 0.046(3) Uiso 0.5 1 d PD B 2 H91 H 1.0438 0.9477 0.3302 0.055 Uiso 0.5 1 calc PR B 2 C92 C 0.9435(14) 0.8780(13) 0.3726(8) 0.066(3) Uiso 0.5 1 d PD B 2 H92A H 0.9863 0.8169 0.387 0.079 Uiso 0.5 1 calc PR B 2 H92B H 0.8747 0.8612 0.3641 0.079 Uiso 0.5 1 calc PR B 2 C93 C 0.9742(10) 0.9880(12) 0.3953(6) 0.048(3) Uiso 0.5 1 d PD B 2 C94 C 0.8938(12) 1.0664(14) 0.4081(7) 0.079(4) Uiso 0.5 1 d PD B 2 H94 H 0.8348 1.0744 0.3763 0.095 Uiso 0.5 1 calc PR B 2 C95 C 0.9554(17) 1.1795(17) 0.4330(9) 0.111(6) Uiso 0.5 1 d PD B 2 H95A H 1.0119 1.1933 0.4158 0.133 Uiso 0.5 1 calc PR B 2 H95B H 0.9159 1.2447 0.4328 0.133 Uiso 0.5 1 calc PR B 2 C96 C 0.9776(16) 1.1109(17) 0.4976(9) 0.092(5) Uiso 0.5 1 d PD B 2 H96 H 0.9807 1.1562 0.5339 0.111 Uiso 0.5 1 calc PR B 2 C97 C 1.0666(16) 1.042(2) 0.4983(10) 0.126(6) Uiso 0.5 1 d PD B 2 H97A H 1.1243 1.0865 0.5119 0.152 Uiso 0.5 1 calc PR B 2 H97B H 1.0684 0.9822 0.5267 0.152 Uiso 0.5 1 calc PR B 2 C98 C 1.0669(13) 1.0002(18) 0.4406(8) 0.097(5) Uiso 0.5 1 d PD B 2 H98A H 1.0972 0.9286 0.4462 0.116 Uiso 0.5 1 calc PR B 2 H98B H 1.109 1.0467 0.4225 0.116 Uiso 0.5 1 calc PR B 2 C99 C 0.8809(12) 1.0467(17) 0.4769(7) 0.074(4) Uiso 0.5 1 d PD B 2 C991 C 0.8605(15) 0.9319(15) 0.4915(10) 0.097(5) Uiso 0.5 1 d PD B 2 H99A H 0.8179 0.8991 0.4571 0.145 Uiso 0.5 1 calc PR B 2 H99B H 0.8299 0.9307 0.5258 0.145 Uiso 0.5 1 calc PR B 2 H99C H 0.9202 0.8914 0.5009 0.145 Uiso 0.5 1 calc PR B 2 C992 C 0.7893(17) 1.119(2) 0.4780(13) 0.132(7) Uiso 0.5 1 d PD B 2 H99D H 0.7334 1.0726 0.4748 0.198 Uiso 0.5 1 calc PR B 2 H99E H 0.7792 1.169 0.4444 0.198 Uiso 0.5 1 calc PR B 2 H99F H 0.7993 1.1593 0.5154 0.198 Uiso 0.5 1 calc PR B 2 C11 C 0.7590(5) 0.7703(7) 0.2045(3) 0.0356(19) Uani 1 1 d . . . C12 C 0.8323(5) 0.6992(7) 0.1891(3) 0.039(2) Uani 1 1 d . . . C13 C 0.8187(5) 0.5875(7) 0.1780(3) 0.038(2) Uani 1 1 d . . . H13 H 0.8682 0.5447 0.1687 0.045 Uiso 1 1 calc R . . C14 C 0.7309(6) 0.5417(6) 0.1810(3) 0.038(2) Uani 1 1 d . . . C15 C 0.6579(6) 0.6047(7) 0.1934(3) 0.046(2) Uani 1 1 d . . . H15 H 0.5975 0.5734 0.1931 0.055 Uiso 1 1 calc R . . C16 C 0.6721(6) 0.7133(7) 0.2063(3) 0.040(2) Uani 1 1 d . . . C21 C 0.7229(5) 0.1186(7) 0.7054(3) 0.037(2) Uani 1 1 d . . . C22 C 0.8060(5) 0.0801(7) 0.6823(3) 0.0380(19) Uani 1 1 d . . . C23 C 0.8158(6) -0.0265(8) 0.6637(3) 0.047(2) Uani 1 1 d . . . H23 H 0.871 -0.047 0.65 0.056 Uiso 1 1 calc R . . C24 C 0.7460(6) -0.1008(6) 0.6655(3) 0.0382(19) Uani 1 1 d . . . C25 C 0.6632(5) -0.0746(6) 0.6843(3) 0.0366(19) Uani 1 1 d . . . H25 H 0.6153 -0.127 0.6847 0.044 Uiso 1 1 calc R . . C26 C 0.6520(5) 0.0295(6) 0.7026(3) 0.0309(18) Uani 1 1 d . . . C31 C 0.7418(5) 0.6220(7) 0.8040(3) 0.038(2) Uani 1 1 d . . . C32 C 0.6699(5) 0.6947(6) 0.8176(3) 0.037(2) Uani 1 1 d . . . C33 C 0.6842(6) 0.8041(6) 0.8285(3) 0.040(2) Uani 1 1 d . . . H33 H 0.6342 0.8471 0.837 0.048 Uiso 1 1 calc R . . C34 C 0.7722(6) 0.8508(6) 0.8267(3) 0.0379(19) Uani 1 1 d . . . C35 C 0.8494(6) 0.7874(7) 0.8164(3) 0.040(2) Uani 1 1 d . . . H35 H 0.91 0.8181 0.817 0.048 Uiso 1 1 calc R . . C36 C 0.8324(5) 0.6779(7) 0.8054(3) 0.038(2) Uani 1 1 d . . . C41 C 0.7762(5) 0.2742(7) 0.2988(3) 0.0355(19) Uani 1 1 d . . . C42 C 0.8527(5) 0.3540(7) 0.3030(3) 0.041(2) Uani 1 1 d . . . C43 C 0.8456(6) 0.4577(8) 0.3211(3) 0.051(2) Uani 1 1 d . . . H43 H 0.895 0.5074 0.3192 0.061 Uiso 1 1 calc R . . C44 C 0.7646(7) 0.4912(7) 0.3426(3) 0.051(2) Uani 1 1 d . . . C45 C 0.6862(6) 0.4188(8) 0.3419(3) 0.052(2) Uani 1 1 d . . . H45 H 0.6319 0.4398 0.3566 0.062 Uiso 1 1 calc R . . C46 C 0.6936(6) 0.3169(8) 0.3189(3) 0.047(2) Uani 1 1 d . . . N11 N 0.9224(5) 0.7435(7) 0.1797(3) 0.057(2) Uani 1 1 d . . . N12 N 0.7173(6) 0.4238(6) 0.1708(3) 0.0488(19) Uani 1 1 d . . . N13 N 0.5896(6) 0.7809(7) 0.2179(4) 0.062(2) Uani 1 1 d . . . N21 N 0.8865(6) 0.1561(7) 0.6808(4) 0.066(2) Uani 1 1 d . . . N22 N 0.7603(7) -0.2154(7) 0.6478(3) 0.065(2) Uani 1 1 d . . . N23 N 0.5607(5) 0.0569(6) 0.7210(3) 0.0451(17) Uani 1 1 d . . . N31 N 0.5763(4) 0.6497(6) 0.8250(3) 0.0491(18) Uani 1 1 d . . . N32 N 0.7852(6) 0.9687(6) 0.8370(3) 0.0477(18) Uani 1 1 d . . . N33 N 0.9158(5) 0.6149(6) 0.7950(3) 0.0509(18) Uani 1 1 d . . . N41 N 0.9402(5) 0.3264(7) 0.2809(3) 0.0497(18) Uani 1 1 d . . . N42 N 0.7550(8) 0.6045(7) 0.3632(4) 0.075(2) Uani 1 1 d . . . N43 N 0.6084(5) 0.2481(7) 0.3177(3) 0.055(2) Uani 1 1 d . . . N51 N 0.8373(4) 0.3268(5) 0.8150(3) 0.0437(17) Uani 1 1 d . . . H51A H 0.892 0.2998 0.807 0.066 Uiso 1 1 calc R . . H51B H 0.8425 0.3992 0.819 0.066 Uiso 1 1 calc R . . H51C H 0.7877 0.3105 0.7846 0.066 Uiso 1 1 calc R . . N71 N 0.5910(4) 0.3918(5) 0.7163(2) 0.0398(16) Uani 1 1 d . . . H71A H 0.6151 0.4232 0.752 0.06 Uiso 1 1 calc R . . H71B H 0.6155 0.3247 0.7158 0.06 Uiso 1 1 calc R . . H71C H 0.5267 0.3878 0.7107 0.06 Uiso 1 1 calc R . . N81 N 0.6638(4) 0.0643(6) 0.1882(3) 0.0485(17) Uani 1 1 d . . . H81A H 0.7047 0.0279 0.217 0.073 Uiso 1 1 calc R . . H81B H 0.6123 0.0226 0.1737 0.073 Uiso 1 1 calc R . . H81C H 0.6447 0.1254 0.2038 0.073 Uiso 1 1 calc R . . O11 O 0.7692(4) 0.8708(5) 0.2142(2) 0.0460(14) Uani 1 1 d . . . O21 O 0.7150(4) 0.2123(4) 0.7264(2) 0.0483(14) Uani 1 1 d . . . O31 O 0.7309(3) 0.5187(4) 0.7957(2) 0.0389(13) Uani 1 1 d . . . O41 O 0.7829(4) 0.1793(4) 0.2769(2) 0.0450(14) Uani 1 1 d . . . O111 O 0.9476(4) 0.8370(5) 0.1966(3) 0.0573(16) Uani 1 1 d . . . O112 O 0.9702(5) 0.6900(5) 0.1513(4) 0.090(2) Uani 1 1 d . . . O121 O 0.7833(5) 0.3705(5) 0.1574(3) 0.0581(16) Uani 1 1 d . . . O122 O 0.6399(5) 0.3831(5) 0.1763(3) 0.0609(16) Uani 1 1 d . . . O131 O 0.5107(5) 0.7658(7) 0.1845(3) 0.087(2) Uani 1 1 d . . . O132 O 0.6066(4) 0.8413(6) 0.2614(4) 0.081(2) Uani 1 1 d . . . O211 O 0.8898(8) 0.2379(10) 0.7025(6) 0.222(8) Uani 1 1 d . . . O212 O 0.9502(5) 0.1259(6) 0.6569(4) 0.115(3) Uani 1 1 d . . . O221 O 0.8309(6) -0.2334(6) 0.6232(3) 0.092(2) Uani 1 1 d . . . O222 O 0.7042(6) -0.2833(6) 0.6595(3) 0.079(2) Uani 1 1 d . . . O231 O 0.5226(4) -0.0155(5) 0.7455(2) 0.0565(16) Uani 1 1 d . . . O232 O 0.5256(4) 0.1494(5) 0.7101(3) 0.0648(17) Uani 1 1 d . . . O311 O 0.5529(4) 0.5566(5) 0.8098(3) 0.0572(16) Uani 1 1 d . . . O312 O 0.5216(5) 0.7090(7) 0.8480(4) 0.124(4) Uani 1 1 d . . . O321 O 0.7168(5) 1.0242(5) 0.8445(2) 0.0572(16) Uani 1 1 d . . . O322 O 0.8659(5) 1.0053(5) 0.8368(3) 0.0728(18) Uani 1 1 d . . . O331 O 0.9952(4) 0.6355(6) 0.8249(3) 0.077(2) Uani 1 1 d . . . O332 O 0.9016(4) 0.5412(5) 0.7572(3) 0.075(2) Uani 1 1 d . . . O411 O 0.9705(4) 0.2337(6) 0.2881(3) 0.0670(18) Uani 1 1 d . . . O412 O 0.9801(4) 0.4013(5) 0.2574(3) 0.0637(17) Uani 1 1 d . . . O421 O 0.8189(7) 0.6687(7) 0.3572(4) 0.111(3) Uani 1 1 d . . . O422 O 0.6867(6) 0.6293(7) 0.3840(4) 0.108(3) Uani 1 1 d . . . O431 O 0.5475(5) 0.2792(5) 0.3467(3) 0.0729(18) Uani 1 1 d . . . O432 O 0.5989(6) 0.1643(9) 0.2883(4) 0.163(5) Uani 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 C51 0.053(5) 0.020(4) 0.095(7) -0.003(5) 0.008(5) -0.009(4) C52 0.038(4) 0.039(4) 0.067(5) 0.006(4) 0.014(4) -0.013(4) C53 0.057(5) 0.026(4) 0.044(5) 0.009(4) 0.008(4) -0.003(4) C54 0.051(5) 0.034(4) 0.028(4) -0.007(3) 0.001(3) -0.014(4) C55 0.035(4) 0.085(6) 0.058(5) -0.012(5) 0.001(4) -0.003(4) C56 0.062(6) 0.102(8) 0.038(5) 0.001(5) -0.021(4) 0.031(6) C57 0.133(10) 0.131(11) 0.047(6) 0.034(7) 0.008(7) 0.076(9) C58 0.081(7) 0.070(6) 0.083(7) 0.047(6) 0.013(5) 0.022(5) C59 0.049(5) 0.087(7) 0.038(5) 0.000(5) 0.007(4) 0.016(5) C591 0.074(7) 0.085(7) 0.059(6) 0.014(5) 0.020(5) 0.016(5) C592 0.084(6) 0.061(6) 0.048(5) -0.029(4) -0.003(4) 0.006(5) C71 0.088(6) 0.041(5) 0.045(5) 0.002(4) 0.016(4) -0.002(5) C72 0.128(8) 0.041(5) 0.056(6) 0.001(4) 0.000(5) 0.016(5) C73 0.126(8) 0.050(6) 0.033(5) -0.004(4) 0.012(5) 0.008(5) C74 0.115(8) 0.058(6) 0.034(5) -0.008(4) -0.011(5) 0.002(6) C75 0.142(9) 0.057(6) 0.047(5) -0.009(4) 0.010(6) 0.035(6) C76 0.177(13) 0.076(8) 0.047(6) -0.008(5) 0.023(7) 0.025(8) C77 0.177(13) 0.106(11) 0.094(9) 0.003(7) 0.051(9) 0.022(10) C78 0.143(10) 0.116(9) 0.058(7) 0.012(6) 0.041(7) -0.011(8) C79 0.131(10) 0.050(6) 0.098(9) -0.006(6) -0.039(8) 0.036(7) C791 0.205(14) 0.083(9) 0.083(8) 0.010(6) -0.062(9) 0.025(9) C792 0.26(2) 0.118(12) 0.116(11) -0.014(9) -0.088(12) -0.023(13) C81 0.086(7) 0.069(7) 0.041(5) 0.001(5) 0.002(5) -0.028(5) C82 0.082(7) 0.084(8) 0.121(10) -0.012(7) 0.016(7) -0.010(6) C83 0.089(7) 0.040(5) 0.056(6) 0.003(4) 0.024(5) 0.009(5) C84 0.048(5) 0.071(7) 0.079(7) -0.007(5) 0.024(5) -0.005(5) C85 0.124(9) 0.096(8) 0.091(8) -0.044(7) 0.047(7) -0.039(7) C86 0.095(8) 0.058(7) 0.071(7) 0.000(5) -0.010(6) 0.002(6) C87 0.070(6) 0.086(7) 0.048(5) 0.001(5) 0.008(5) 0.028(5) C88 0.066(6) 0.107(8) 0.079(7) -0.003(6) 0.031(5) -0.006(5) C89 0.058(6) 0.078(7) 0.078(7) -0.036(6) 0.008(5) -0.012(6) C891 0.082(7) 0.087(8) 0.070(7) -0.006(6) -0.003(6) 0.033(6) C892 0.105(10) 0.197(15) 0.109(10) -0.033(10) 0.013(8) 0.020(10) C11 0.031(5) 0.038(6) 0.040(4) 0.004(4) 0.011(4) 0.004(4) C12 0.031(5) 0.047(6) 0.039(5) 0.001(4) 0.010(4) -0.003(4) C13 0.033(5) 0.047(6) 0.033(4) 0.000(4) 0.008(3) -0.009(4) C14 0.055(6) 0.027(5) 0.034(4) 0.000(3) 0.014(4) -0.005(4) C15 0.033(5) 0.051(6) 0.049(5) 0.013(4) 0.000(4) -0.011(4) C16 0.038(5) 0.042(6) 0.044(5) 0.005(4) 0.014(4) -0.004(4) C21 0.031(5) 0.059(6) 0.019(4) 0.007(4) 0.000(3) 0.004(4) C22 0.040(5) 0.042(5) 0.028(4) -0.003(4) -0.002(4) 0.001(4) C23 0.047(5) 0.069(7) 0.025(4) 0.007(4) 0.011(4) 0.016(5) C24 0.053(5) 0.027(5) 0.033(4) -0.004(3) 0.005(4) 0.008(4) C25 0.040(5) 0.033(5) 0.037(4) -0.008(4) 0.010(4) -0.004(4) C26 0.037(5) 0.039(5) 0.015(4) -0.004(3) 0.003(3) -0.004(4) C31 0.042(5) 0.043(6) 0.027(4) -0.001(4) 0.005(3) 0.000(4) C32 0.036(5) 0.038(6) 0.039(4) 0.004(4) 0.010(4) -0.002(4) C33 0.057(6) 0.027(5) 0.037(4) -0.003(3) 0.011(4) 0.010(4) C34 0.041(5) 0.037(5) 0.033(4) 0.001(4) 0.001(4) -0.005(4) C35 0.040(5) 0.047(6) 0.030(4) 0.002(4) 0.001(4) -0.011(4) C36 0.031(5) 0.046(6) 0.039(4) -0.002(4) 0.009(3) 0.002(4) C41 0.033(5) 0.042(5) 0.029(4) -0.003(4) 0.002(4) -0.011(4) C42 0.030(5) 0.039(6) 0.053(5) -0.004(4) 0.006(4) 0.009(4) C43 0.052(6) 0.055(6) 0.040(5) 0.009(4) 0.000(4) -0.002(5) C44 0.061(6) 0.056(6) 0.034(5) -0.009(4) 0.007(4) -0.002(5) C45 0.055(6) 0.061(7) 0.039(5) 0.000(4) 0.012(4) 0.018(5) C46 0.034(5) 0.072(7) 0.036(5) -0.007(4) 0.011(4) -0.003(5) N11 0.034(4) 0.074(6) 0.067(5) -0.020(4) 0.023(4) -0.003(4) N12 0.054(5) 0.057(6) 0.035(4) -0.006(3) 0.009(4) -0.015(4) N13 0.038(5) 0.073(6) 0.080(6) 0.006(5) 0.024(4) -0.009(4) N21 0.053(5) 0.074(6) 0.076(5) -0.027(5) 0.028(4) -0.021(5) N22 0.090(7) 0.052(6) 0.047(4) -0.007(4) 0.002(4) 0.034(5) N23 0.047(4) 0.042(5) 0.046(4) -0.007(4) 0.010(3) 0.011(4) N31 0.032(4) 0.033(5) 0.079(5) -0.010(4) 0.005(4) -0.008(4) N32 0.068(6) 0.032(5) 0.042(4) 0.003(3) 0.008(4) -0.009(4) N33 0.050(5) 0.034(4) 0.076(5) 0.010(4) 0.031(4) -0.006(4) N41 0.038(4) 0.054(5) 0.057(5) -0.012(4) 0.010(4) -0.016(4) N42 0.095(7) 0.048(6) 0.083(6) -0.010(5) 0.024(5) 0.011(5) N43 0.056(5) 0.074(6) 0.040(4) -0.003(4) 0.022(4) -0.007(4) N51 0.031(4) 0.036(4) 0.061(4) -0.017(4) 0.003(3) 0.003(3) N71 0.045(4) 0.044(4) 0.030(3) -0.005(3) 0.006(3) 0.003(3) N81 0.043(4) 0.051(4) 0.053(4) -0.012(4) 0.012(3) 0.003(3) O11 0.040(3) 0.033(4) 0.065(4) -0.001(3) 0.010(3) 0.002(2) O21 0.059(4) 0.030(4) 0.053(3) -0.003(3) 0.006(3) 0.007(3) O31 0.029(3) 0.039(4) 0.050(3) -0.008(2) 0.009(2) -0.006(2) O41 0.044(3) 0.044(4) 0.045(3) -0.017(3) 0.008(3) -0.007(3) O111 0.047(4) 0.047(4) 0.081(4) -0.022(3) 0.021(3) -0.015(3) O112 0.056(4) 0.060(4) 0.168(7) -0.051(5) 0.056(5) -0.027(3) O121 0.069(4) 0.045(4) 0.064(4) -0.008(3) 0.021(3) -0.012(3) O122 0.069(4) 0.050(4) 0.070(4) -0.010(3) 0.028(3) -0.029(3) O131 0.048(4) 0.126(6) 0.086(5) 0.016(4) 0.013(4) 0.013(4) O132 0.050(4) 0.065(5) 0.137(6) -0.032(5) 0.039(4) -0.011(3) O211 0.211(12) 0.196(11) 0.335(16) -0.210(12) 0.228(12) -0.165(10) O212 0.074(5) 0.085(5) 0.217(9) 0.030(5) 0.100(6) 0.010(4) O221 0.102(5) 0.079(5) 0.102(5) -0.027(4) 0.037(5) 0.039(4) O222 0.123(6) 0.039(4) 0.078(5) -0.001(3) 0.027(4) 0.004(4) O231 0.052(4) 0.059(4) 0.066(4) 0.000(3) 0.032(3) -0.009(3) O232 0.055(4) 0.055(4) 0.093(5) 0.011(4) 0.036(3) 0.014(3) O311 0.031(3) 0.041(4) 0.105(5) -0.010(3) 0.027(3) -0.006(3) O312 0.069(5) 0.099(6) 0.227(10) -0.083(6) 0.084(6) -0.009(4) O321 0.082(4) 0.040(4) 0.051(4) -0.012(3) 0.016(3) 0.011(4) O322 0.076(5) 0.050(4) 0.092(5) 0.007(3) 0.018(4) -0.016(4) O331 0.022(3) 0.114(5) 0.094(5) 0.031(4) 0.011(3) 0.002(4) O332 0.062(4) 0.043(4) 0.136(6) -0.005(4) 0.057(4) 0.000(3) O411 0.050(4) 0.063(5) 0.088(5) -0.002(4) 0.013(3) 0.009(4) O412 0.048(4) 0.063(4) 0.083(4) -0.002(4) 0.020(3) -0.018(3) O421 0.156(8) 0.054(5) 0.127(7) -0.029(4) 0.035(6) -0.016(5) O422 0.115(6) 0.076(6) 0.140(7) -0.036(5) 0.045(6) 0.019(5) O431 0.066(4) 0.082(5) 0.079(4) 0.003(4) 0.034(4) 0.007(4) O432 0.133(8) 0.217(11) 0.177(9) -0.154(9) 0.123(7) -0.118(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C51 N51 1.439(10) . ? C51 C53 1.490(11) . ? C51 C52 1.509(11) . ? C52 C53 1.497(10) . ? C53 C54 1.508(10) . ? C53 C58 1.543(11) . ? C54 C55 1.536(10) . ? C54 C59 1.579(10) . ? C55 C56 1.574(11) . ? C56 C57 1.502(16) . ? C56 C59 1.571(11) . ? C57 C58 1.554(14) . ? C59 C591 1.488(11) . ? C59 C592 1.515(12) . ? N61 C61 1.561(17) . ? C61 C63 1.401(16) . ? C61 C62 1.492(19) . ? C62 C63 1.480(18) . ? C63 C68 1.486(19) . ? C63 C64 1.546(18) . ? C64 C69 1.626(17) . ? C64 C65 1.64(2) . ? C65 C66 1.64(2) . ? C66 C67 1.51(3) . ? C66 C69 1.56(2) . ? C67 C68 1.41(2) . ? C69 C691 1.48(2) . ? C69 C692 1.56(2) . ? C71 N71 1.453(9) . ? C71 C72 1.490(11) . ? C71 C73 1.504(11) . ? C72 C73 1.504(12) . ? C73 C74 1.439(13) . ? C73 C78 1.589(13) . ? C74 C75 1.593(12) . ? C74 C79 1.623(13) . ? C75 C76 1.551(13) . ? C76 C79 1.503(18) . ? C76 C77 1.516(17) . ? C77 C78 1.554(15) . ? C79 C792 1.483(19) . ? C79 C791 1.514(14) . ? C81 C82 1.403(13) . ? C81 N81 1.487(10) . ? C81 C83 1.491(12) . ? C82 C83 1.468(13) . ? C83 C84 1.479(12) . ? C83 C88 1.548(12) . ? C84 C85 1.481(14) . ? C84 C89 1.627(13) . ? C85 C86 1.528(13) . ? C86 C87 1.461(13) . ? C86 C89 1.464(14) . ? C87 C88 1.578(12) . ? C89 C892 1.439(15) . ? C89 C891 1.512(14) . ? N91 C91 1.539(16) . ? C91 C93 1.391(15) . ? C91 C92 1.458(19) . ? C92 C93 1.469(19) . ? C93 C98 1.483(19) . ? C93 C94 1.554(17) . ? C94 C99 1.616(17) . ? C94 C95 1.66(2) . ? C95 C96 1.65(2) . ? C96 C97 1.51(3) . ? C96 C99 1.555(19) . ? C97 C98 1.40(2) . ? C99 C991 1.48(2) . ? C99 C992 1.57(2) . ? C11 O11 1.249(8) . ? C11 C16 1.416(11) . ? C11 C12 1.445(11) . ? C12 C13 1.392(11) . ? C12 N11 1.436(10) . ? C13 C14 1.372(10) . ? C14 C15 1.359(11) . ? C14 N12 1.463(10) . ? C15 C16 1.363(11) . ? C16 N13 1.491(11) . ? C21 O21 1.252(9) . ? C21 C22 1.454(10) . ? C21 C26 1.469(11) . ? C22 C23 1.382(11) . ? C22 N21 1.471(10) . ? C23 C24 1.343(11) . ? C24 C25 1.360(10) . ? C24 N22 1.480(10) . ? C25 C26 1.355(10) . ? C26 N23 1.469(9) . ? C31 O31 1.279(9) . ? C31 C32 1.427(11) . ? C31 C36 1.441(11) . ? C32 C33 1.366(10) . ? C32 N31 1.469(10) . ? C33 C34 1.372(10) . ? C34 C35 1.393(11) . ? C34 N32 1.463(10) . ? C35 C36 1.372(10) . ? C36 N33 1.462(10) . ? C41 O41 1.269(8) . ? C41 C46 1.433(11) . ? C41 C42 1.441(11) . ? C42 C43 1.340(11) . ? C42 N41 1.463(10) . ? C43 C44 1.392(11) . ? C44 C45 1.412(12) . ? C44 N42 1.473(12) . ? C45 C46 1.359(11) . ? C46 N43 1.460(10) . ? N11 O112 1.210(8) . ? N11 O111 1.232(9) . ? N12 O121 1.222(8) . ? N12 O122 1.228(8) . ? N13 O132 1.209(9) . ? N13 O131 1.218(9) . ? N21 O211 1.109(11) . ? N21 O212 1.195(9) . ? N22 O222 1.212(10) . ? N22 O221 1.255(10) . ? N23 O231 1.223(8) . ? N23 O232 1.237(8) . ? N31 O311 1.212(8) . ? N31 O312 1.247(9) . ? N32 O321 1.217(8) . ? N32 O322 1.222(8) . ? N33 O331 1.204(8) . ? N33 O332 1.226(9) . ? N41 O411 1.208(9) . ? N41 O412 1.246(9) . ? N42 O422 1.194(10) . ? N42 O421 1.223(11) . ? N43 O432 1.211(10) . ? N43 O431 1.242(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N51 C51 C53 123.5(6) . . ? N51 C51 C52 119.1(7) . . ? C53 C51 C52 59.9(5) . . ? C53 C52 C51 59.4(5) . . ? C51 C53 C52 60.7(5) . . ? C51 C53 C54 118.8(7) . . ? C52 C53 C54 118.6(6) . . ? C51 C53 C58 116.8(7) . . ? C52 C53 C58 121.8(7) . . ? C54 C53 C58 111.5(7) . . ? C53 C54 C55 110.2(7) . . ? C53 C54 C59 112.1(6) . . ? C55 C54 C59 88.3(5) . . ? C54 C55 C56 85.6(5) . . ? C57 C56 C59 111.7(9) . . ? C57 C56 C55 110.3(8) . . ? C59 C56 C55 87.2(6) . . ? C56 C57 C58 111.5(7) . . ? C53 C58 C57 114.0(7) . . ? C591 C59 C592 110.7(7) . . ? C591 C59 C56 117.7(8) . . ? C592 C59 C56 113.4(8) . . ? C591 C59 C54 117.6(7) . . ? C592 C59 C54 111.0(7) . . ? C56 C59 C54 84.2(6) . . ? C63 C61 C62 61.4(9) . . ? C63 C61 N61 118.4(14) . . ? C62 C61 N61 115.9(13) . . ? C63 C62 C61 56.3(8) . . ? C61 C63 C62 62.3(9) . . ? C61 C63 C68 120.3(14) . . ? C62 C63 C68 119.7(14) . . ? C61 C63 C64 124.3(13) . . ? C62 C63 C64 113.6(14) . . ? C68 C63 C64 109.2(13) . . ? C63 C64 C69 110.1(14) . . ? C63 C64 C65 104.4(15) . . ? C69 C64 C65 88.2(12) . . ? C64 C65 C66 83.5(12) . . ? C67 C66 C69 107.5(18) . . ? C67 C66 C65 107.5(17) . . ? C69 C66 C65 90.4(15) . . ? C68 C67 C66 111.9(18) . . ? C67 C68 C63 123.5(17) . . ? C691 C69 C66 124.9(17) . . ? C691 C69 C692 106.3(15) . . ? C66 C69 C692 115.3(19) . . ? C691 C69 C64 114.0(16) . . ? C66 C69 C64 86.8(12) . . ? C692 C69 C64 107.3(15) . . ? N71 C71 C72 119.3(8) . . ? N71 C71 C73 120.8(7) . . ? C72 C71 C73 60.3(6) . . ? C71 C72 C73 60.3(6) . . ? C74 C73 C71 122.2(8) . . ? C74 C73 C72 121.5(9) . . ? C71 C73 C72 59.4(5) . . ? C74 C73 C78 112.8(8) . . ? C71 C73 C78 111.6(8) . . ? C72 C73 C78 119.2(8) . . ? C73 C74 C75 110.4(9) . . ? C73 C74 C79 111.0(8) . . ? C75 C74 C79 85.9(6) . . ? C76 C75 C74 83.6(7) . . ? C79 C76 C77 112.8(10) . . ? C79 C76 C75 91.7(9) . . ? C77 C76 C75 111.1(10) . . ? C76 C77 C78 109.3(9) . . ? C77 C78 C73 111.8(9) . . ? C792 C79 C76 116.3(11) . . ? C792 C79 C791 111.0(11) . . ? C76 C79 C791 118.1(13) . . ? C792 C79 C74 109.3(10) . . ? C76 C79 C74 84.0(7) . . ? C791 C79 C74 115.4(8) . . ? C82 C81 N81 123.2(9) . . ? C82 C81 C83 60.9(6) . . ? N81 C81 C83 122.6(8) . . ? C81 C82 C83 62.5(7) . . ? C82 C83 C84 123.3(9) . . ? C82 C83 C81 56.6(6) . . ? C84 C83 C81 121.2(8) . . ? C82 C83 C88 120.0(9) . . ? C84 C83 C88 110.8(7) . . ? C81 C83 C88 114.9(8) . . ? C83 C84 C85 113.4(8) . . ? C83 C84 C89 108.1(8) . . ? C85 C84 C89 84.4(8) . . ? C84 C85 C86 87.7(9) . . ? C87 C86 C89 114.5(9) . . ? C87 C86 C85 109.1(8) . . ? C89 C86 C85 88.6(9) . . ? C86 C87 C88 111.6(8) . . ? C83 C88 C87 110.6(7) . . ? C892 C89 C86 114.6(10) . . ? C892 C89 C891 107.9(10) . . ? C86 C89 C891 118.3(9) . . ? C892 C89 C84 112.6(9) . . ? C86 C89 C84 84.6(8) . . ? C891 C89 C84 117.6(8) . . ? C93 C91 C92 62.0(9) . . ? C93 C91 N91 125.2(12) . . ? C92 C91 N91 121.8(13) . . ? C91 C92 C93 56.8(9) . . ? C91 C93 C92 61.2(9) . . ? C91 C93 C98 118.7(13) . . ? C92 C93 C98 118.8(14) . . ? C91 C93 C94 119.8(12) . . ? C92 C93 C94 117.1(14) . . ? C98 C93 C94 112.4(12) . . ? C93 C94 C99 108.6(12) . . ? C93 C94 C95 103.0(14) . . ? C99 C94 C95 87.5(12) . . ? C96 C95 C94 82.2(12) . . ? C97 C96 C99 113.3(18) . . ? C97 C96 C95 107.1(16) . . ? C99 C96 C95 90.1(15) . . ? C98 C97 C96 111.2(18) . . ? C97 C98 C93 120.0(17) . . ? C991 C99 C96 127.6(17) . . ? C991 C99 C992 109.3(16) . . ? C96 C99 C992 112.5(19) . . ? C991 C99 C94 114.8(16) . . ? C96 C99 C94 86.7(12) . . ? C992 C99 C94 101.0(15) . . ? O11 C11 C16 123.0(7) . . ? O11 C11 C12 124.7(7) . . ? C16 C11 C12 112.2(7) . . ? C13 C12 N11 115.8(7) . . ? C13 C12 C11 123.6(7) . . ? N11 C12 C11 120.5(7) . . ? C14 C13 C12 118.8(8) . . ? C15 C14 C13 120.5(8) . . ? C15 C14 N12 120.6(8) . . ? C13 C14 N12 118.8(8) . . ? C14 C15 C16 120.7(8) . . ? C15 C16 C11 124.1(8) . . ? C15 C16 N13 119.4(7) . . ? C11 C16 N13 116.3(8) . . ? O21 C21 C22 125.0(8) . . ? O21 C21 C26 125.4(7) . . ? C22 C21 C26 109.6(7) . . ? C23 C22 C21 123.4(8) . . ? C23 C22 N21 117.4(8) . . ? C21 C22 N21 119.1(8) . . ? C24 C23 C22 120.4(7) . . ? C23 C24 C25 122.1(7) . . ? C23 C24 N22 119.2(8) . . ? C25 C24 N22 118.7(8) . . ? C26 C25 C24 118.5(7) . . ? C25 C26 N23 117.6(7) . . ? C25 C26 C21 125.9(7) . . ? N23 C26 C21 116.5(7) . . ? O31 C31 C32 125.1(7) . . ? O31 C31 C36 123.3(7) . . ? C32 C31 C36 111.4(7) . . ? C33 C32 C31 124.2(7) . . ? C33 C32 N31 116.6(7) . . ? C31 C32 N31 119.1(7) . . ? C32 C33 C34 120.1(7) . . ? C33 C34 C35 121.0(7) . . ? C33 C34 N32 119.2(8) . . ? C35 C34 N32 119.8(8) . . ? C36 C35 C34 117.3(7) . . ? C35 C36 C31 125.8(7) . . ? C35 C36 N33 115.2(7) . . ? C31 C36 N33 118.9(7) . . ? O41 C41 C46 125.9(7) . . ? O41 C41 C42 121.8(7) . . ? C46 C41 C42 112.2(7) . . ? C43 C42 C41 123.8(8) . . ? C43 C42 N41 116.3(8) . . ? C41 C42 N41 119.6(7) . . ? C42 C43 C44 120.1(8) . . ? C43 C44 C45 120.6(8) . . ? C43 C44 N42 121.4(9) . . ? C45 C44 N42 117.9(9) . . ? C46 C45 C44 117.0(8) . . ? C45 C46 C41 125.9(8) . . ? C45 C46 N43 113.9(8) . . ? C41 C46 N43 120.2(8) . . ? O112 N11 O111 120.5(7) . . ? O112 N11 C12 118.8(8) . . ? O111 N11 C12 120.6(7) . . ? O121 N12 O122 123.2(7) . . ? O121 N12 C14 118.7(7) . . ? O122 N12 C14 118.1(8) . . ? O132 N13 O131 126.3(9) . . ? O132 N13 C16 116.8(8) . . ? O131 N13 C16 116.8(8) . . ? O211 N21 O212 120.7(9) . . ? O211 N21 C22 121.2(9) . . ? O212 N21 C22 118.0(8) . . ? O222 N22 O221 126.1(8) . . ? O222 N22 C24 117.1(8) . . ? O221 N22 C24 116.7(9) . . ? O231 N23 O232 123.7(7) . . ? O231 N23 C26 117.1(7) . . ? O232 N23 C26 119.3(7) . . ? O311 N31 O312 120.4(7) . . ? O311 N31 C32 121.0(7) . . ? O312 N31 C32 118.5(7) . . ? O321 N32 O322 124.1(7) . . ? O321 N32 C34 119.5(8) . . ? O322 N32 C34 116.4(8) . . ? O331 N33 O332 122.5(8) . . ? O331 N33 C36 119.0(8) . . ? O332 N33 C36 118.5(7) . . ? O411 N41 O412 124.5(7) . . ? O411 N41 C42 117.9(7) . . ? O412 N41 C42 117.5(8) . . ? O422 N42 O421 123.5(10) . . ? O422 N42 C44 119.8(10) . . ? O421 N42 C44 116.7(9) . . ? O432 N43 O431 122.4(8) . . ? O432 N43 C46 119.5(8) . . ? O431 N43 C46 118.0(8) . . ?