# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences # This journal is (c) The Royal Society of Chemistry and Owner Societies 2011 data_global _journal_name_full Photochem.Photobiol.Sci. _journal_coden_cambridge 0171 #TrackingRef 'MacGillivray_1.cif' #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2009-11-17 _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 _audit_update_record ? _publ_contact_author_name 'MacGillivray, Leonard R.' _publ_contact_author_address ;Department of Chemistry E555 Chemistry Building The University of Iowa Iowa City, IA 52242-1294 USA ; _publ_contact_author_fax 1-319-335-1270 _publ_contact_author_phone 1-319-335-3504 #============================================================================== # # TITLE AND AUTHOR LIST loop_ _publ_author_name _publ_author_address M.B.J.Atkinson ;Department of Chemistry E553 Chemistry Building The University of Iowa Iowa City, IA 52242-1294 USA ; A.N.Sokolov ;Department of Chemistry 305 Chemistry Building The University of Iowa Iowa City, IA 52242-1294 USA ; D.-K.Bucar ;Department of Chemistry E553 Chemistry Building The University of Iowa Iowa City, IA 52242-1294 USA ; M.T.Mwangi ;Department of Chemistry 305 Chemistry Building The University of Iowa Iowa City, IA 52242-1294 USA ; L.R.MacGillivray ;Department of Chemistry E555 Chemistry Building The University of Iowa Iowa City, IA 52242-1294 USA ; S.V.S.Mariappan '' M.C.Tiedman '' #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_1 _database_code_depnum_ccdc_archive 'CCDC 802315' #TrackingRef 'MacGillivray_1.cif' _audit_creation_date 2009-11-17T11:02:11-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C30 H28 N2 O4 S2' _chemical_formula_moiety 'C22 H18 N2 S2, C8 H10 O4' _chemical_formula_weight 544.66 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _cell_length_a 12.8295(14) _cell_length_b 14.5618(16) _cell_length_c 14.3340(15) _cell_angle_alpha 90 _cell_angle_beta 95.724(5) _cell_angle_gamma 90 _cell_volume 2664.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.88 _cell_measurement_reflns_used 6171 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description blade _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.24 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.966 _exptl_absorpt_correction_T_max 0.990 #----------------------------------------------------------------------------# # 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 0.0324 _diffrn_reflns_av_unetI/netI 0.026 _diffrn_reflns_number 8919 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_detector_area_resol_mean 9 _reflns_number_total 2351 _reflns_number_gt 1956 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL v6.1 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # 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^)+(0.0531P)^2^+1.7217P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2351 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.047 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.099 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.256 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.043 #----------------------------------------------------------------------------# # 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' S S 0.1246 0.1234 '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 0.24406(15) 0.31736(13) 0.89507(13) 0.0353(5) Uani 1 1 d . . . C2 C 0.24474(14) 0.22956(13) 0.86058(13) 0.0318(4) Uani 1 1 d . . . C3 C 0.33914(13) 0.18177(12) 0.86290(12) 0.0276(4) Uani 1 1 d . . . C4 C 0.42886(14) 0.22550(13) 0.90423(13) 0.0324(4) Uani 1 1 d . . . C5 C 0.42023(15) 0.31421(13) 0.93666(13) 0.0347(4) Uani 1 1 d . . . C6 C 0.46512(14) 0.02701(13) 0.84597(14) 0.0331(4) Uani 1 1 d . . . C7 C 0.48028(13) -0.06156(12) 0.79523(13) 0.0292(4) Uani 1 1 d . . . C8 C 0.45840(13) -0.14339(12) 0.83549(13) 0.0286(4) Uani 1 1 d . . . C9 C 0.47704(13) -0.22867(12) 0.79314(13) 0.0279(4) Uani 1 1 d . . . C10 C 0.45338(14) -0.31425(13) 0.83345(14) 0.0330(4) Uani 1 1 d . . . C11 C 0.47615(15) -0.39492(13) 0.79200(14) 0.0388(5) Uani 1 1 d . . . C12 C 0.27247(14) 0.57075(12) 1.01826(13) 0.0317(4) Uani 1 1 d . . . C13 C 0.29745(13) 0.65383(13) 1.07870(13) 0.0310(4) Uani 1 1 d . . . C14 C 0.27473(13) 0.73855(13) 1.04638(13) 0.0311(4) Uani 1 1 d . . . C15 C 0.35099(16) 0.63543(14) 1.17496(13) 0.0389(5) Uani 1 1 d . . . H1 H 0.1804 0.3483 0.8924 0.042 Uiso 1 1 calc R . . H1O H 0.3392 0.473 0.9828 0.07 Uiso 1 1 calc R . . H2 H 0.1826 0.2021 0.8358 0.038 Uiso 1 1 calc R . . H4 H 0.4932 0.1955 0.9098 0.039 Uiso 1 1 calc R . . H5 H 0.4808 0.3431 0.9631 0.042 Uiso 1 1 calc R . . H6A H 0.5188 0.0706 0.8326 0.04 Uiso 1 1 calc R . . H6B H 0.4715 0.0161 0.9131 0.04 Uiso 1 1 calc R . . H8 H 0.4302 -0.143 0.8928 0.034 Uiso 1 1 calc R . . H10 H 0.4218 -0.3152 0.8891 0.04 Uiso 1 1 calc R . . H11 H 0.46 -0.4503 0.8195 0.047 Uiso 1 1 calc R . . H14 H 0.2922 0.7872 1.087 0.037 Uiso 1 1 calc R . . H15A H 0.367 0.6927 1.2064 0.058 Uiso 1 1 calc R . . H15B H 0.4146 0.602 1.1697 0.058 Uiso 1 1 calc R . . H15C H 0.3055 0.5999 1.2102 0.058 Uiso 1 1 calc R . . N1 N 0.33062(12) 0.36094(11) 0.93245(11) 0.0345(4) Uani 1 1 d . . . O1 O 0.35502(10) 0.51836(10) 1.01509(11) 0.0465(4) Uani 1 1 d . . . O2 O 0.18618(10) 0.55426(9) 0.97922(10) 0.0412(4) Uani 1 1 d . . . S1 S 0.33624(3) 0.07399(3) 0.80861(4) 0.03425(17) 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 0.0327(10) 0.0345(11) 0.0386(11) 0.0020(8) 0.0029(8) 0.0082(8) C2 0.0266(9) 0.0311(10) 0.0371(10) 0.0006(8) 0.0004(7) 0.0014(7) C3 0.0290(9) 0.0241(9) 0.0300(9) 0.0019(7) 0.0038(7) 0.0004(7) C4 0.0271(9) 0.0301(10) 0.0396(11) -0.0029(8) 0.0009(8) 0.0029(7) C5 0.0327(10) 0.0348(11) 0.0359(11) -0.0047(9) -0.0001(8) -0.0013(8) C6 0.0279(9) 0.0280(10) 0.0427(11) -0.0027(8) -0.0008(8) 0.0045(7) C7 0.0211(8) 0.0281(10) 0.0374(10) -0.0013(8) -0.0014(7) 0.0033(7) C8 0.0234(9) 0.0312(10) 0.0314(10) 0.0004(8) 0.0030(7) 0.0028(7) C9 0.0207(8) 0.0266(10) 0.0357(10) 0.0006(8) -0.0006(7) 0.0008(7) C10 0.0286(9) 0.0319(11) 0.0383(11) 0.0050(8) 0.0024(8) 0.0017(7) C11 0.0386(11) 0.0256(10) 0.0514(12) 0.0067(9) 0.0001(9) -0.0020(8) C12 0.0322(10) 0.0270(10) 0.0362(10) -0.0007(8) 0.0057(8) -0.0003(8) C13 0.0249(9) 0.0303(10) 0.0383(10) -0.0051(8) 0.0057(7) -0.0003(7) C14 0.0250(9) 0.0281(10) 0.0408(11) -0.0087(8) 0.0056(7) -0.0003(7) C15 0.0454(12) 0.0341(11) 0.0367(11) -0.0054(9) 0.0018(9) -0.0016(9) N1 0.0389(9) 0.0295(9) 0.0352(9) -0.0028(7) 0.0035(7) 0.0033(7) O1 0.0379(8) 0.0344(8) 0.0665(10) -0.0199(7) 0.0024(7) 0.0041(6) O2 0.0377(8) 0.0361(8) 0.0482(9) -0.0069(6) -0.0040(6) -0.0029(6) S1 0.0264(3) 0.0252(3) 0.0500(3) -0.0055(2) -0.0019(2) 0.00140(18) #----------------------------------------------------------------------------# # 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 H1 0.93 . ? C2 C1 1.371(3) . ? C2 H2 0.93 . ? C3 C2 1.394(2) . ? C3 C4 1.395(2) . ? C4 C5 1.381(3) . ? C4 H4 0.93 . ? C5 H5 0.93 . ? C6 H6A 0.97 . ? C6 H6B 0.97 . ? C7 C6 1.503(2) . ? C7 C7 1.438(4) 2_656 ? C7 C8 1.365(2) . ? C8 C9 1.413(2) . ? C8 H8 0.93 . ? C9 C10 1.419(3) . ? C9 C9 1.422(4) 2_656 ? C10 C11 1.361(3) . ? C10 H10 0.93 . ? C11 C11 1.404(4) 2_656 ? C11 H11 0.93 . ? C12 C13 1.504(3) . ? C13 C15 1.503(3) . ? C14 C13 1.340(3) . ? C14 C14 1.454(4) 7_567 ? C14 H14 0.93 . ? C15 H15A 0.96 . ? C15 H15B 0.96 . ? C15 H15C 0.96 . ? N1 C1 1.343(3) . ? N1 C5 1.332(2) . ? O1 C12 1.310(2) . ? O1 H1O 0.82 . ? O2 C12 1.214(2) . ? S1 C3 1.7506(18) . ? S1 C6 1.8199(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C2 C3 119.57(17) . . ? C1 C2 H2 120.2 . . ? C2 C1 H1 118.3 . . ? C2 C3 C4 117.41(16) . . ? C2 C3 S1 117.19(13) . . ? C3 C2 H2 120.2 . . ? C3 C4 H4 120.7 . . ? C3 S1 C6 103.17(8) . . ? C4 C3 S1 125.33(14) . . ? C4 C5 H5 118 . . ? C5 C4 C3 118.66(16) . . ? C5 C4 H4 120.7 . . ? C5 N1 C1 116.88(16) . . ? C7 C6 H6A 109.7 . . ? C7 C6 H6B 109.7 . . ? C7 C6 S1 109.75(12) . . ? C7 C7 C6 120.70(10) 2_656 . ? C7 C8 C9 122.32(16) . . ? C7 C8 H8 118.8 . . ? C8 C7 C6 120.16(17) . . ? C8 C7 C7 119.13(11) . 2_656 ? C8 C9 C10 122.99(16) . . ? C8 C9 C9 118.44(10) . 2_656 ? C9 C10 H10 119.5 . . ? C9 C8 H8 118.8 . . ? C10 C11 C11 120.34(12) . 2_656 ? C10 C11 H11 119.8 . . ? C10 C9 C9 118.56(11) . 2_656 ? C11 C10 C9 121.07(17) . . ? C11 C10 H10 119.5 . . ? C11 C11 H11 119.8 2_656 . ? C12 O1 H1O 109.5 . . ? C13 C14 C14 126.0(2) . 7_567 ? C13 C14 H14 117 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? C14 C13 C12 121.00(17) . . ? C14 C13 C15 123.06(17) . . ? C14 C14 H14 117 7_567 . ? C15 C13 C12 115.92(16) . . ? H6A C6 H6B 108.2 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N1 C1 C2 123.34(17) . . ? N1 C1 H1 118.3 . . ? N1 C5 C4 124.08(17) . . ? N1 C5 H5 118 . . ? O1 C12 C13 111.22(15) . . ? O2 C12 C13 123.85(17) . . ? O2 C12 O1 124.91(17) . . ? S1 C6 H6A 109.7 . . ? S1 C6 H6B 109.7 . . ? # Attachment 'MacGillivray_2.cif' #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_2 _database_code_depnum_ccdc_archive 'CCDC 802316' #TrackingRef 'MacGillivray_2.cif' _audit_creation_date 2009-11-17T15:28:18-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C28 H24 N2 O4' _chemical_formula_moiety 'C20 H14 N2, C8 H10 O4' _chemical_formula_weight 452.49 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _cell_length_a 14.5252(16) _cell_length_b 6.9630(8) _cell_length_c 23.665(3) _cell_angle_alpha 90 _cell_angle_beta 102.029(5) _cell_angle_gamma 90 _cell_volume 2340.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 190(2) _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _cell_measurement_reflns_used 9849 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.09 _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.977 _exptl_absorpt_correction_T_max 0.992 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 190(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_unetI/netI 0.0321 _diffrn_reflns_number 15098 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_detector_area_resol_mean 9 _reflns_number_total 4117 _reflns_number_gt 3126 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL v6.1 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # 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^)+(0.0637P)^2^+0.1787P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4117 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1078 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.179 _refine_diff_density_min -0.211 _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 C1 C 0.67840(10) -0.1563(2) 0.29842(7) 0.0392(4) Uani 1 1 d . . . C2 C 0.62103(10) 0.0026(2) 0.28585(7) 0.0360(4) Uani 1 1 d . . . C3 C 0.52388(9) -0.0142(2) 0.28286(6) 0.0296(3) Uani 1 1 d . . . C4 C 0.48977(10) -0.1971(2) 0.29065(6) 0.0330(4) Uani 1 1 d . . . C5 C 0.55219(10) -0.3475(2) 0.30323(7) 0.0383(4) Uani 1 1 d . . . C6 C 0.45955(9) 0.15421(19) 0.26819(6) 0.0286(3) Uani 1 1 d . . . C7 C 0.45829(10) 0.2339(2) 0.21484(6) 0.0342(4) Uani 1 1 d . . . C8 C 0.39490(10) 0.3819(2) 0.19203(7) 0.0368(4) Uani 1 1 d . . . C9 C 0.33355(10) 0.4490(2) 0.22361(6) 0.0321(3) Uani 1 1 d . . . C10 C 0.33301(9) 0.37603(18) 0.27921(6) 0.0277(3) Uani 1 1 d . . . C11 C 0.26680(10) 0.4500(2) 0.30997(6) 0.0338(4) Uani 1 1 d . . . C12 C 0.26167(11) 0.3810(2) 0.36266(7) 0.0392(4) Uani 1 1 d . . . C13 C 0.32501(10) 0.2383(2) 0.38809(6) 0.0368(4) Uani 1 1 d . . . C14 C 0.39321(10) 0.1633(2) 0.36119(6) 0.0297(3) Uani 1 1 d . . . C15 C 0.39747(9) 0.22660(19) 0.30383(6) 0.0261(3) Uani 1 1 d . . . C16 C 0.45799(10) 0.0187(2) 0.39503(6) 0.0324(3) Uani 1 1 d . . . C17 C 0.42203(11) -0.1516(2) 0.41272(7) 0.0401(4) Uani 1 1 d . . . C18 C 0.48309(11) -0.2874(2) 0.44211(7) 0.0452(4) Uani 1 1 d . . . C19 C 0.61130(11) -0.0968(2) 0.44115(7) 0.0423(4) Uani 1 1 d . . . C20 C 0.55524(10) 0.0473(2) 0.41170(6) 0.0374(4) Uani 1 1 d . . . C21 C 0.64456(10) -0.0347(2) 0.13947(6) 0.0329(3) Uani 1 1 d . . . C22 C 0.57049(10) -0.1812(2) 0.11659(7) 0.0343(4) Uani 1 1 d . . . C23 C 0.48728(10) -0.1346(2) 0.08198(6) 0.0365(4) Uani 1 1 d . . . C24 C 0.45483(10) 0.0544(2) 0.06094(6) 0.0355(4) Uani 1 1 d . . . C25 C 0.37001(10) 0.1036(2) 0.02842(6) 0.0332(4) Uani 1 1 d . . . C26 C 0.29409(10) -0.0404(2) 0.00685(6) 0.0351(4) Uani 1 1 d . . . C27 C 0.59426(12) -0.3864(2) 0.13390(8) 0.0451(4) Uani 1 1 d . . . C28 C 0.34622(12) 0.3095(2) 0.01320(8) 0.0465(4) Uani 1 1 d . . . H1 H 0.7426 -0.1418 0.3004 0.047 Uiso 1 1 calc R . . H1O H 0.7684 -0.0228 0.1646 0.073 Uiso 1 1 calc R . . H2 H 0.6468 0.1208 0.2794 0.043 Uiso 1 1 calc R . . H4 H 0.4256 -0.2174 0.2874 0.04 Uiso 1 1 calc R . . H5 H 0.5283 -0.4683 0.3089 0.046 Uiso 1 1 calc R . . H7 H 0.5004 0.189 0.1932 0.041 Uiso 1 1 calc R . . H8 H 0.3951 0.433 0.1557 0.044 Uiso 1 1 calc R . . H9 H 0.2911 0.5449 0.2083 0.039 Uiso 1 1 calc R . . H11 H 0.2262 0.5477 0.2936 0.041 Uiso 1 1 calc R . . H12 H 0.2166 0.4278 0.3818 0.047 Uiso 1 1 calc R . . H13 H 0.3211 0.1921 0.4244 0.044 Uiso 1 1 calc R . . H17 H 0.3575 -0.1735 0.4048 0.048 Uiso 1 1 calc R . . H18 H 0.458 -0.4008 0.4531 0.054 Uiso 1 1 calc R . . H19 H 0.6759 -0.0764 0.4514 0.051 Uiso 1 1 calc R . . H20 H 0.582 0.1621 0.4031 0.045 Uiso 1 1 calc R . . H23 H 0.4459 -0.2357 0.0702 0.044 Uiso 1 1 calc R . . H24 H 0.4976 0.1542 0.071 0.043 Uiso 1 1 calc R . . H27A H 0.5427 -0.4681 0.1169 0.068 Uiso 1 1 calc R . . H27B H 0.6057 -0.3973 0.1752 0.068 Uiso 1 1 calc R . . H27C H 0.6496 -0.4245 0.1206 0.068 Uiso 1 1 calc R . . H28A H 0.2997 0.3533 0.0337 0.07 Uiso 1 1 calc R . . H28B H 0.3218 0.3201 -0.0276 0.07 Uiso 1 1 calc R . . H28C H 0.4019 0.3867 0.0238 0.07 Uiso 1 1 calc R . . H3O H 0.1695 -0.0454 -0.0178 0.069 Uiso 1 1 calc R . . N1 N 0.64562(9) -0.33006(18) 0.30782(6) 0.0390(3) Uani 1 1 d . . . N2 N 0.57705(9) -0.26377(19) 0.45559(6) 0.0439(4) Uani 1 1 d . . . O1 O 0.73027(7) -0.10865(15) 0.15340(6) 0.0489(3) Uani 1 1 d . . . O2 O 0.62870(7) 0.13406(15) 0.14588(5) 0.0442(3) Uani 1 1 d . . . O3 O 0.20891(7) 0.03878(15) -0.00747(5) 0.0462(3) Uani 1 1 d . . . O4 O 0.30631(8) -0.21147(16) 0.00352(5) 0.0548(3) 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 0.0217(8) 0.0387(9) 0.0557(10) -0.0007(7) 0.0047(7) 0.0013(7) C2 0.0273(8) 0.0304(8) 0.0493(9) 0.0031(7) 0.0057(7) -0.0026(7) C3 0.0250(8) 0.0285(8) 0.0332(8) -0.0048(6) 0.0016(6) 0.0017(6) C4 0.0219(7) 0.0295(8) 0.0451(9) -0.0060(7) 0.0010(6) -0.0012(6) C5 0.0300(9) 0.0255(8) 0.0564(10) -0.0056(7) 0.0020(7) -0.0014(7) C6 0.0219(7) 0.0234(7) 0.0379(8) -0.0014(6) 0.0000(6) -0.0027(6) C7 0.0286(8) 0.0343(8) 0.0406(9) 0.0000(7) 0.0096(7) 0.0000(7) C8 0.0357(9) 0.0370(9) 0.0372(9) 0.0074(7) 0.0065(7) -0.0001(7) C9 0.0277(8) 0.0254(8) 0.0401(8) 0.0037(6) -0.0004(6) 0.0013(6) C10 0.0234(7) 0.0227(7) 0.0338(8) -0.0027(6) -0.0016(6) -0.0015(6) C11 0.0293(8) 0.0288(8) 0.0394(9) -0.0038(7) -0.0015(6) 0.0065(6) C12 0.0359(9) 0.0441(10) 0.0367(9) -0.0074(7) 0.0055(7) 0.0107(7) C13 0.0365(9) 0.0437(9) 0.0286(8) -0.0010(7) 0.0029(7) 0.0061(7) C14 0.0266(8) 0.0274(8) 0.0312(8) -0.0024(6) -0.0028(6) -0.0003(6) C15 0.0207(7) 0.0213(7) 0.0339(8) -0.0033(6) 0.0003(6) -0.0030(6) C16 0.0317(8) 0.0347(8) 0.0278(7) -0.0017(6) -0.0009(6) 0.0040(7) C17 0.0306(9) 0.0460(10) 0.0424(9) 0.0096(7) 0.0043(7) 0.0023(7) C18 0.0416(10) 0.0444(10) 0.0480(10) 0.0166(8) 0.0055(8) 0.0040(8) C19 0.0314(9) 0.0457(10) 0.0426(9) -0.0003(8) -0.0086(7) 0.0021(7) C20 0.0357(9) 0.0337(9) 0.0374(8) -0.0009(7) -0.0047(7) -0.0022(7) C21 0.0269(8) 0.0334(9) 0.0390(8) 0.0017(7) 0.0078(6) -0.0013(7) C22 0.0297(8) 0.0326(8) 0.0404(9) 0.0019(7) 0.0069(7) -0.0040(7) C23 0.0334(9) 0.0307(8) 0.0445(9) -0.0011(7) 0.0063(7) -0.0095(7) C24 0.0336(9) 0.0315(8) 0.0407(9) -0.0024(7) 0.0065(7) -0.0078(7) C25 0.0325(8) 0.0329(9) 0.0345(8) -0.0015(6) 0.0076(7) -0.0033(7) C26 0.0332(9) 0.0400(10) 0.0307(8) -0.0010(7) 0.0035(6) -0.0008(7) C27 0.0425(10) 0.0342(9) 0.0554(11) 0.0058(8) 0.0027(8) -0.0083(7) C28 0.0432(10) 0.0372(9) 0.0567(11) 0.0023(8) 0.0053(8) -0.0010(8) N1 0.0275(7) 0.0319(7) 0.0546(9) -0.0044(6) 0.0017(6) 0.0024(6) N2 0.0393(8) 0.0447(8) 0.0429(8) 0.0087(6) -0.0028(6) 0.0052(6) O1 0.0261(6) 0.0335(6) 0.0833(9) -0.0032(6) 0.0025(6) -0.0028(5) O2 0.0314(6) 0.0335(7) 0.0650(8) -0.0106(5) 0.0041(5) -0.0027(5) O3 0.0337(6) 0.0418(7) 0.0574(7) -0.0057(6) -0.0039(5) -0.0017(5) O4 0.0425(7) 0.0349(7) 0.0774(9) -0.0120(6) -0.0092(6) -0.0015(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 C2 1.380(2) . ? C1 H1 0.93 . ? C2 H2 0.93 . ? C3 C2 1.4031(19) . ? C3 C4 1.393(2) . ? C3 C6 1.4947(19) . ? C4 H4 0.93 . ? C5 C4 1.376(2) . ? C5 H5 0.93 . ? C6 C7 1.376(2) . ? C7 C8 1.412(2) . ? C7 H7 0.93 . ? C8 H8 0.93 . ? C9 C8 1.359(2) . ? C9 H9 0.93 . ? C10 C11 1.418(2) . ? C10 C9 1.412(2) . ? C11 H11 0.93 . ? C12 C11 1.353(2) . ? C12 C13 1.402(2) . ? C12 H12 0.93 . ? C13 H13 0.93 . ? C14 C13 1.386(2) . ? C15 C10 1.4392(19) . ? C15 C14 1.441(2) . ? C15 C6 1.4476(19) . ? C16 C14 1.4919(19) . ? C16 C17 1.395(2) . ? C16 C20 1.399(2) . ? C17 H17 0.93 . ? C18 C17 1.381(2) . ? C18 H18 0.93 . ? C18 N2 1.345(2) . ? C19 H19 0.93 . ? C20 C19 1.385(2) . ? C20 H20 0.93 . ? C21 C22 1.500(2) . ? C22 C23 1.351(2) . ? C22 C27 1.506(2) . ? C23 H23 0.93 . ? C24 C23 1.451(2) . ? C24 H24 0.93 . ? C25 C24 1.353(2) . ? C25 C26 1.499(2) . ? C25 C28 1.501(2) . ? C27 H27A 0.96 . ? C27 H27B 0.96 . ? C27 H27C 0.96 . ? C28 H28A 0.96 . ? C28 H28B 0.96 . ? C28 H28C 0.96 . ? N1 C1 1.3356(19) . ? N1 C5 1.3442(19) . ? N2 C19 1.337(2) . ? O1 C21 1.3240(17) . ? O1 H1O 0.82 . ? O2 C21 1.2128(17) . ? O3 C26 1.3322(17) . ? O3 H3O 0.82 . ? O4 C26 1.2094(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C2 C3 119.98(14) . . ? C1 C2 H2 120 . . ? C1 N1 C5 117.22(12) . . ? C2 C1 H1 118.6 . . ? C2 C3 C6 121.31(12) . . ? C3 C2 H2 120 . . ? C3 C4 H4 120.4 . . ? C4 C3 C2 116.84(12) . . ? C4 C3 C6 121.73(12) . . ? C4 C5 H5 118.1 . . ? C5 C4 C3 119.20(13) . . ? C5 C4 H4 120.4 . . ? C6 C7 C8 121.89(14) . . ? C6 C7 H7 119.1 . . ? C7 C6 C15 120.22(13) . . ? C7 C6 C3 114.70(12) . . ? C7 C8 H8 120.3 . . ? C8 C7 H7 119.1 . . ? C8 C9 C10 121.35(14) . . ? C8 C9 H9 119.3 . . ? C9 C10 C11 118.92(13) . . ? C9 C10 C15 120.51(13) . . ? C9 C8 C7 119.36(14) . . ? C9 C8 H8 120.3 . . ? C10 C11 H11 119.4 . . ? C10 C15 C14 116.78(12) . . ? C10 C15 C6 116.59(12) . . ? C10 C9 H9 119.3 . . ? C11 C10 C15 120.56(13) . . ? C11 C12 C13 119.36(14) . . ? C11 C12 H12 120.3 . . ? C12 C11 C10 121.15(14) . . ? C12 C11 H11 119.4 . . ? C12 C13 H13 118.7 . . ? C13 C12 H12 120.3 . . ? C13 C14 C15 119.49(13) . . ? C13 C14 C16 116.02(13) . . ? C14 C13 C12 122.53(14) . . ? C14 C13 H13 118.7 . . ? C14 C15 C6 126.62(13) . . ? C15 C14 C16 124.48(12) . . ? C15 C6 C3 124.97(13) . . ? C16 C17 H17 120.3 . . ? C16 C20 H20 120.3 . . ? C17 C16 C14 120.06(13) . . ? C17 C16 C20 117.09(13) . . ? C17 C18 H18 118.3 . . ? C18 C17 C16 119.46(14) . . ? C18 C17 H17 120.3 . . ? C19 C20 C16 119.46(14) . . ? C19 C20 H20 120.3 . . ? C19 N2 C18 117.31(14) . . ? C20 C16 C14 122.82(13) . . ? C20 C19 H19 118.4 . . ? C21 C22 C27 116.14(13) . . ? C21 O1 H1O 109.5 . . ? C22 C23 C24 127.74(14) . . ? C22 C23 H23 116.1 . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? C23 C22 C21 122.62(13) . . ? C23 C22 C27 121.24(14) . . ? C23 C24 H24 116 . . ? C24 C23 H23 116.1 . . ? C24 C25 C26 122.85(14) . . ? C24 C25 C28 120.98(14) . . ? C25 C24 C23 128.07(14) . . ? C25 C24 H24 116 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? C26 C25 C28 116.15(13) . . ? C26 O3 H3O 109.5 . . ? H27A C27 H27B 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? H28A C28 H28B 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N1 C1 C2 122.83(13) . . ? N1 C1 H1 118.6 . . ? N1 C5 C4 123.86(14) . . ? N1 C5 H5 118.1 . . ? N2 C18 C17 123.30(15) . . ? N2 C18 H18 118.3 . . ? N2 C19 C20 123.20(14) . . ? N2 C19 H19 118.4 . . ? O1 C21 C22 113.06(13) . . ? O2 C21 C22 124.31(13) . . ? O2 C21 O1 122.61(14) . . ? O3 C26 C25 112.85(13) . . ? O4 C26 C25 124.98(14) . . ? O4 C26 O3 122.15(14) . . ? # Attachment 'MacGillivray_3.cif' #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_3 _database_code_depnum_ccdc_archive 'CCDC 802317' #TrackingRef 'MacGillivray_3.cif' _audit_creation_date 2009-11-17T15:10:37-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C56 H48 N4 O8' _chemical_formula_moiety 'C16 H20 O8, 2(C20 H14 N2)' _chemical_formula_weight 904.98 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _cell_length_a 31.686(4) _cell_length_b 9.6115(11) _cell_length_c 29.601(3) _cell_angle_alpha 90 _cell_angle_beta 93.685(5) _cell_angle_gamma 90 _cell_volume 8996.3(18) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.88 _cell_measurement_reflns_used 19394 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3808 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.09 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'HKL Scalepack (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.977 _exptl_absorpt_correction_T_max 0.995 #----------------------------------------------------------------------------# # 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 0.0601 _diffrn_reflns_av_unetI/netI 0.0509 _diffrn_reflns_number 27238 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_detector_area_resol_mean 9 _reflns_number_total 7918 _reflns_number_gt 5330 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL v6.1 (Sheldrick, 1997)' _computing_publication_material 'SHELXTL v6.1 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # 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. The difference Fourier map suggests that the cyclobutane derivative is disordered over two positions being related through a two-fold rotation (approximate occupacies 0.96:0.04). However, a satisfying model of disorder could not be achieved despite the extensive use of restraints and constraints. ; _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^)+(0.0897P)^2^+2.9560P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 7918 _refine_ls_number_parameters 621 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0963 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1634 _refine_ls_wR_factor_gt 0.1483 _refine_ls_goodness_of_fit_ref 1.07 _refine_ls_restrained_S_all 1.07 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.577 _refine_diff_density_min -0.452 _refine_diff_density_rms 0.052 #----------------------------------------------------------------------------# # 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 0.16087(8) 0.7304(3) 0.41154(9) 0.0359(6) Uani 1 1 d . . . C2 C 0.12392(8) 0.7991(3) 0.38520(9) 0.0359(6) Uani 1 1 d . . . C3 C 0.11554(8) 0.9573(3) 0.39251(9) 0.0367(6) Uani 1 1 d . . . C4 C 0.14625(8) 1.0479(3) 0.41823(9) 0.0384(7) Uani 1 1 d . . . C6 C 0.09566(9) 1.2355(3) 0.43203(10) 0.0407(7) Uani 1 1 d . . . C7 C 0.08486(8) 0.7127(3) 0.39528(10) 0.0466(7) Uani 1 1 d . . . C8 C 0.17310(9) 1.2566(3) 0.46035(11) 0.0542(8) Uani 1 1 d . . . C9 C 0.17565(8) 0.8132(2) 0.32419(8) 0.0279(6) Uani 1 1 d . . . C10 C 0.12920(8) 0.8250(3) 0.33245(9) 0.0335(6) Uani 1 1 d . . . C11 C 0.11418(8) 0.9787(3) 0.33826(9) 0.0338(6) Uani 1 1 d . . . C12 C 0.13907(8) 1.0959(3) 0.32116(9) 0.0355(6) Uani 1 1 d . . . C13 C 0.12597(8) 1.2200(3) 0.30511(9) 0.0347(6) Uani 1 1 d . . . C14 C 0.08031(8) 1.2609(3) 0.30129(9) 0.0367(6) Uani 1 1 d . . . C15 C 0.10101(8) 0.7418(3) 0.29851(9) 0.0394(7) Uani 1 1 d . . . C16 C 0.15688(9) 1.3285(3) 0.29151(12) 0.0526(8) Uani 1 1 d . . . C17 C 0.22383(9) 0.0985(3) 0.05193(10) 0.0405(7) Uani 1 1 d . . . C18 C 0.18026(8) 0.0859(3) 0.04983(9) 0.0368(7) Uani 1 1 d . . . C19 C 0.16157(8) -0.0111(3) 0.07742(8) 0.0292(6) Uani 1 1 d . . . C20 C 0.18862(7) -0.0986(3) 0.10282(8) 0.0301(6) Uani 1 1 d . . . C21 C 0.23181(8) -0.0805(3) 0.10241(9) 0.0351(6) Uani 1 1 d . . . C22 C 0.11462(7) -0.0174(2) 0.07801(8) 0.0283(6) Uani 1 1 d . . . C23 C 0.09102(7) -0.0059(2) 0.11776(8) 0.0261(6) Uani 1 1 d . . . C24 C 0.10856(7) 0.0232(2) 0.16295(8) 0.0267(6) Uani 1 1 d . . . C25 C 0.08233(8) 0.0249(3) 0.19863(9) 0.0320(6) Uani 1 1 d . . . C26 C 0.03839(8) 0.0081(3) 0.19230(10) 0.0375(7) Uani 1 1 d . . . C27 C 0.02079(8) -0.0119(3) 0.14967(10) 0.0365(7) Uani 1 1 d . . . C28 C 0.04608(8) -0.0219(3) 0.11197(9) 0.0319(6) Uani 1 1 d . . . C29 C 0.02627(8) -0.0440(3) 0.06851(10) 0.0389(7) Uani 1 1 d . . . C30 C 0.04943(9) -0.0513(3) 0.03129(10) 0.0414(7) Uani 1 1 d . . . C31 C 0.09328(8) -0.0382(3) 0.03618(9) 0.0368(6) Uani 1 1 d . . . C32 C 0.15306(7) 0.0657(2) 0.17532(8) 0.0266(6) Uani 1 1 d . . . C33 C 0.17736(8) -0.0045(3) 0.20930(8) 0.0312(6) Uani 1 1 d . . . C34 C 0.21761(8) 0.0407(3) 0.22147(9) 0.0350(6) Uani 1 1 d . . . C35 C 0.21189(7) 0.2199(3) 0.17054(9) 0.0318(6) Uani 1 1 d . . . C36 C 0.17128(7) 0.1816(2) 0.15650(8) 0.0284(6) Uani 1 1 d . . . C37 C 0.01567(9) 0.3373(3) 0.05208(11) 0.0499(8) Uani 1 1 d . . . C38 C 0.05934(8) 0.3430(3) 0.05627(10) 0.0444(7) Uani 1 1 d . . . C39 C 0.07905(7) 0.4689(3) 0.06613(8) 0.0288(6) Uani 1 1 d . . . C40 C 0.05315(8) 0.5839(3) 0.06801(9) 0.0356(6) Uani 1 1 d . . . C41 C 0.00979(8) 0.5685(3) 0.06245(9) 0.0394(7) Uani 1 1 d . . . C42 C 0.12602(8) 0.4780(2) 0.07154(8) 0.0285(6) Uani 1 1 d . . . C43 C 0.14977(7) 0.5229(2) 0.11198(8) 0.0247(5) Uani 1 1 d . . . C44 C 0.13254(7) 0.5551(2) 0.15481(8) 0.0266(6) Uani 1 1 d . . . C45 C 0.15853(8) 0.6070(3) 0.18955(9) 0.0320(6) Uani 1 1 d . . . C46 C 0.20222(8) 0.6238(3) 0.18605(9) 0.0334(6) Uani 1 1 d . . . C47 C 0.21981(8) 0.5862(2) 0.14747(9) 0.0314(6) Uani 1 1 d . . . C48 C 0.19466(7) 0.5363(2) 0.10979(8) 0.0282(6) Uani 1 1 d . . . C49 C 0.21423(8) 0.4983(3) 0.06980(9) 0.0352(6) Uani 1 1 d . . . C5 C 0.13868(8) 1.1734(3) 0.43562(9) 0.0382(7) Uani 1 1 d . . . C50 C 0.19096(8) 0.4517(3) 0.03283(9) 0.0385(7) Uani 1 1 d . . . C51 C 0.14706(8) 0.4434(3) 0.03373(9) 0.0354(6) Uani 1 1 d . . . C52 C 0.08791(7) 0.5286(2) 0.16585(8) 0.0268(6) Uani 1 1 d . . . C53 C 0.07063(9) 0.3967(3) 0.16648(10) 0.0442(7) Uani 1 1 d . . . C54 C 0.02999(9) 0.3779(3) 0.17881(11) 0.0509(8) Uani 1 1 d . . . C55 C 0.02174(8) 0.6067(3) 0.19107(9) 0.0397(7) Uani 1 1 d . . . C56 C 0.06208(8) 0.6355(3) 0.17936(9) 0.0363(6) Uani 1 1 d . . . H1O H 0.1929 0.5808 0.4058 0.063 Uiso 1 1 calc R . . H3O H 0.2092 0.7089 0.2925 0.055 Uiso 1 1 calc R . . H3 H 0.0872 0.9707 0.4033 0.044 Uiso 1 1 calc R . . H4 H 0.1737 1.0141 0.4228 0.046 Uiso 1 1 calc R . . H5O H 0.0687 1.3888 0.4455 0.084 Uiso 1 1 calc R . . H7A H 0.0885 0.6188 0.3852 0.07 Uiso 1 1 calc R . . H7B H 0.0602 0.7522 0.3797 0.07 Uiso 1 1 calc R . . H7C H 0.0814 0.713 0.4273 0.07 Uiso 1 1 calc R . . H7O H 0.0502 1.415 0.3031 0.075 Uiso 1 1 calc R . . H8A H 0.1989 1.2039 0.462 0.081 Uiso 1 1 calc R . . H8B H 0.1651 1.277 0.4904 0.081 Uiso 1 1 calc R . . H8C H 0.1773 1.342 0.4444 0.081 Uiso 1 1 calc R . . H11 H 0.0847 0.9873 0.3264 0.041 Uiso 1 1 calc R . . H12 H 0.1681 1.081 0.3216 0.043 Uiso 1 1 calc R . . H15A H 0.104 0.7771 0.2686 0.059 Uiso 1 1 calc R . . H15B H 0.0721 0.7502 0.3059 0.059 Uiso 1 1 calc R . . H15C H 0.1092 0.6456 0.2998 0.059 Uiso 1 1 calc R . . H16A H 0.1569 1.4051 0.3123 0.079 Uiso 1 1 calc R . . H16B H 0.1488 1.3608 0.2615 0.079 Uiso 1 1 calc R . . H16C H 0.1847 1.2888 0.292 0.079 Uiso 1 1 calc R . . H17 H 0.2357 0.1657 0.034 0.049 Uiso 1 1 calc R . . H18 H 0.1635 0.1416 0.0302 0.044 Uiso 1 1 calc R . . H20 H 0.1777 -0.1693 0.1201 0.036 Uiso 1 1 calc R . . H21 H 0.2493 -0.1403 0.1197 0.042 Uiso 1 1 calc R . . H25 H 0.0943 0.0376 0.2279 0.038 Uiso 1 1 calc R . . H26 H 0.0215 0.0107 0.2169 0.045 Uiso 1 1 calc R . . H27 H -0.0084 -0.0193 0.1451 0.044 Uiso 1 1 calc R . . H29 H -0.003 -0.0537 0.0652 0.047 Uiso 1 1 calc R . . H30 H 0.036 -0.0651 0.0028 0.05 Uiso 1 1 calc R . . H31 H 0.1087 -0.0435 0.0106 0.044 Uiso 1 1 calc R . . H33 H 0.1663 -0.0813 0.2236 0.037 Uiso 1 1 calc R . . H34 H 0.2334 -0.008 0.2438 0.042 Uiso 1 1 calc R . . H35 H 0.2237 0.2969 0.1571 0.038 Uiso 1 1 calc R . . H36 H 0.1561 0.2333 0.1344 0.034 Uiso 1 1 calc R . . H37 H 0.0031 0.2513 0.0461 0.06 Uiso 1 1 calc R . . H38 H 0.0753 0.2631 0.0525 0.053 Uiso 1 1 calc R . . H40 H 0.0649 0.6717 0.073 0.043 Uiso 1 1 calc R . . H41 H -0.0069 0.648 0.0633 0.047 Uiso 1 1 calc R . . H45 H 0.1468 0.6321 0.2164 0.038 Uiso 1 1 calc R . . H46 H 0.219 0.6605 0.2101 0.04 Uiso 1 1 calc R . . H47 H 0.2489 0.5934 0.1457 0.038 Uiso 1 1 calc R . . H49 H 0.2434 0.5053 0.069 0.042 Uiso 1 1 calc R . . H50 H 0.2042 0.4255 0.007 0.046 Uiso 1 1 calc R . . H51 H 0.1314 0.4134 0.0079 0.042 Uiso 1 1 calc R . . H53 H 0.0866 0.3203 0.1585 0.053 Uiso 1 1 calc R . . H54 H 0.0193 0.2879 0.1786 0.061 Uiso 1 1 calc R . . H55 H 0.0051 0.6807 0.1996 0.048 Uiso 1 1 calc R . . H56 H 0.0721 0.7265 0.1805 0.044 Uiso 1 1 calc R . . N1 N 0.24979(7) 0.0194(2) 0.07828(8) 0.0386(6) Uani 1 1 d . . . N2 N 0.23518(6) 0.1516(2) 0.20266(7) 0.0339(5) Uani 1 1 d . . . N3 N -0.00949(7) 0.4465(2) 0.05599(8) 0.0389(6) Uani 1 1 d . . . N4 N 0.00510(7) 0.4803(2) 0.19100(8) 0.0370(5) Uani 1 1 d . . . O1 O 0.17323(6) 0.61686(19) 0.39071(6) 0.0420(5) Uani 1 1 d . . . O2 O 0.17605(6) 0.7685(2) 0.44797(7) 0.0514(5) Uani 1 1 d . . . O3 O 0.18413(5) 0.7304(2) 0.29023(6) 0.0367(5) Uani 1 1 d . . . O4 O 0.20282(5) 0.87318(18) 0.34765(6) 0.0354(4) Uani 1 1 d . . . O5 O 0.09309(6) 1.3603(2) 0.44939(8) 0.0561(6) Uani 1 1 d . . . O6 O 0.06509(8) 1.1807(3) 0.41494(13) 0.1180(14) Uani 1 1 d . . . O7 O 0.07545(6) 1.39637(19) 0.30330(8) 0.0501(6) Uani 1 1 d . . . O8 O 0.05112(6) 1.1808(2) 0.29496(7) 0.0507(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 C1 0.0349(16) 0.0371(16) 0.0370(16) 0.0009(13) 0.0119(13) -0.0013(12) C2 0.0275(15) 0.0371(15) 0.0439(16) -0.0006(13) 0.0078(12) -0.0033(12) C3 0.0260(14) 0.0354(15) 0.0490(17) -0.0038(13) 0.0057(12) 0.0020(12) C4 0.0288(15) 0.0381(16) 0.0489(17) -0.0034(13) 0.0071(12) 0.0020(12) C5 0.0335(16) 0.0384(16) 0.0431(16) -0.0011(13) 0.0070(12) -0.0023(13) C6 0.0351(17) 0.0354(16) 0.0512(18) -0.0114(14) -0.0016(13) 0.0010(13) C7 0.0370(17) 0.0435(17) 0.0606(19) 0.0004(15) 0.0119(14) -0.0048(14) C8 0.0361(17) 0.0489(19) 0.078(2) -0.0147(17) 0.0034(15) -0.0026(14) C9 0.0274(14) 0.0242(13) 0.0327(14) 0.0073(12) 0.0063(11) 0.0041(11) C10 0.0254(14) 0.0312(15) 0.0441(16) -0.0004(12) 0.0043(12) -0.0013(11) C11 0.0232(14) 0.0276(14) 0.0506(17) 0.0002(12) 0.0019(12) 0.0018(11) C12 0.0238(14) 0.0300(15) 0.0533(18) -0.0035(13) 0.0061(12) 0.0004(11) C13 0.0290(15) 0.0332(15) 0.0422(16) -0.0030(12) 0.0059(12) -0.0007(12) C14 0.0327(16) 0.0301(16) 0.0480(17) 0.0032(13) 0.0077(13) 0.0017(13) C15 0.0296(15) 0.0366(16) 0.0519(18) -0.0033(13) 0.0019(13) -0.0012(12) C16 0.0350(17) 0.0380(17) 0.086(2) 0.0101(16) 0.0137(16) -0.0016(13) C17 0.0365(17) 0.0419(17) 0.0450(17) 0.0096(14) 0.0164(13) 0.0017(13) C18 0.0366(17) 0.0389(16) 0.0356(15) 0.0088(12) 0.0078(12) 0.0050(13) C19 0.0274(14) 0.0294(14) 0.0312(14) -0.0007(11) 0.0047(11) 0.0032(11) C20 0.0268(15) 0.0282(14) 0.0355(15) 0.0022(11) 0.0041(11) 0.0007(11) C21 0.0292(15) 0.0347(16) 0.0415(16) 0.0036(12) 0.0037(12) 0.0046(12) C22 0.0277(14) 0.0227(13) 0.0342(14) 0.0036(11) -0.0003(11) 0.0027(10) C23 0.0241(13) 0.0191(12) 0.0351(14) 0.0047(11) 0.0013(11) -0.0002(10) C24 0.0267(14) 0.0190(13) 0.0346(14) 0.0031(11) 0.0018(11) -0.0013(10) C25 0.0316(15) 0.0275(14) 0.0375(15) 0.0003(12) 0.0076(12) -0.0028(11) C26 0.0316(16) 0.0353(16) 0.0472(18) 0.0025(13) 0.0146(13) 0.0002(12) C27 0.0213(14) 0.0317(15) 0.0569(19) 0.0034(13) 0.0056(13) -0.0001(11) C28 0.0235(14) 0.0250(14) 0.0467(16) 0.0055(12) -0.0007(12) 0.0006(11) C29 0.0249(15) 0.0326(15) 0.0578(19) 0.0040(14) -0.0081(13) -0.0010(12) C30 0.0404(17) 0.0423(17) 0.0395(17) 0.0007(13) -0.0124(13) 0.0022(13) C31 0.0382(16) 0.0377(16) 0.0341(15) 0.0032(12) -0.0013(12) 0.0039(13) C32 0.0248(13) 0.0263(13) 0.0291(13) -0.0016(11) 0.0037(10) 0.0014(11) C33 0.0328(15) 0.0310(14) 0.0298(14) 0.0033(11) 0.0021(11) -0.0056(11) C34 0.0318(15) 0.0377(16) 0.0346(15) 0.0076(12) -0.0050(12) -0.0043(12) C35 0.0260(14) 0.0277(14) 0.0421(16) 0.0030(12) 0.0047(12) -0.0038(11) C36 0.0254(14) 0.0239(13) 0.0358(14) 0.0031(11) 0.0010(11) 0.0014(10) C37 0.0415(19) 0.0340(17) 0.073(2) -0.0069(15) -0.0020(15) -0.0091(14) C38 0.0298(16) 0.0362(16) 0.066(2) -0.0074(15) -0.0041(14) -0.0006(13) C39 0.0270(14) 0.0299(14) 0.0293(14) -0.0010(11) -0.0001(10) 0.0005(11) C40 0.0314(15) 0.0272(14) 0.0484(17) 0.0024(12) 0.0031(12) 0.0001(12) C41 0.0291(16) 0.0365(16) 0.0526(18) 0.0051(13) 0.0031(13) 0.0037(12) C42 0.0266(14) 0.0231(13) 0.0361(15) 0.0008(11) 0.0033(11) 0.0013(10) C43 0.0224(13) 0.0183(12) 0.0337(14) 0.0048(10) 0.0039(10) 0.0023(10) C44 0.0231(13) 0.0204(12) 0.0362(14) 0.0033(11) 0.0012(11) 0.0013(10) C45 0.0317(15) 0.0327(14) 0.0319(14) 0.0013(12) 0.0030(11) -0.0005(12) C46 0.0299(15) 0.0322(15) 0.0369(15) 0.0014(12) -0.0064(12) -0.0021(11) C47 0.0207(13) 0.0257(14) 0.0474(17) 0.0057(12) -0.0003(12) 0.0029(11) C48 0.0258(14) 0.0205(13) 0.0387(15) 0.0037(11) 0.0037(11) 0.0039(10) C49 0.0232(14) 0.0341(15) 0.0491(17) 0.0019(13) 0.0088(12) 0.0027(11) C50 0.0345(16) 0.0439(17) 0.0386(16) -0.0039(13) 0.0146(13) 0.0020(13) C51 0.0342(16) 0.0373(15) 0.0347(15) -0.0043(12) 0.0020(12) 0.0023(12) C52 0.0252(14) 0.0269(14) 0.0283(13) 0.0015(11) 0.0024(10) -0.0002(11) C53 0.0370(17) 0.0277(15) 0.069(2) 0.0037(14) 0.0160(15) 0.0068(13) C54 0.0393(18) 0.0330(16) 0.083(2) 0.0035(16) 0.0215(16) -0.0025(13) C55 0.0328(16) 0.0324(16) 0.0550(18) -0.0031(13) 0.0103(13) 0.0021(12) C56 0.0294(15) 0.0300(15) 0.0500(17) 0.0005(13) 0.0054(12) -0.0012(11) N1 0.0302(13) 0.0374(13) 0.0492(14) 0.0014(11) 0.0110(11) 0.0024(10) N2 0.0282(12) 0.0360(13) 0.0369(13) 0.0034(10) -0.0024(10) -0.0065(10) N3 0.0285(12) 0.0406(14) 0.0473(14) -0.0026(11) -0.0009(10) -0.0014(11) N4 0.0310(13) 0.0310(13) 0.0502(14) -0.0011(11) 0.0116(10) -0.0008(10) O1 0.0369(12) 0.0355(11) 0.0532(12) 0.0000(9) 0.0004(9) 0.0049(9) O2 0.0632(14) 0.0559(13) 0.0354(12) 0.0009(10) 0.0043(10) 0.0155(11) O3 0.0256(10) 0.0488(12) 0.0354(10) -0.0046(9) 0.0007(8) 0.0091(9) O4 0.0265(10) 0.0326(10) 0.0472(11) -0.0048(9) 0.0027(8) -0.0009(8) O5 0.0352(12) 0.0415(13) 0.0914(17) -0.0161(12) 0.0024(12) 0.0042(9) O6 0.0457(15) 0.079(2) 0.224(4) -0.085(2) -0.0381(19) 0.0238(14) O7 0.0288(11) 0.0296(11) 0.0932(17) 0.0003(10) 0.0132(11) 0.0030(8) O8 0.0325(11) 0.0396(12) 0.0801(15) 0.0026(11) 0.0037(10) 0.0005(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 C1 C2 1.516(4) . ? C2 C3 1.561(4) . ? C2 C7 1.536(4) . ? C3 H3 0.98 . ? C4 C3 1.480(4) . ? C4 C5 1.339(4) . ? C4 H4 0.93 . ? C5 C8 1.504(4) . ? C6 C5 1.486(4) . ? C6 O6 1.187(3) . ? C7 H7A 0.96 . ? C7 H7B 0.96 . ? C7 H7C 0.96 . ? C8 H8A 0.96 . ? C8 H8B 0.96 . ? C8 H8C 0.96 . ? C9 C10 1.512(3) . ? C10 C15 1.527(3) . ? C10 C2 1.601(4) . ? C11 C10 1.565(4) . ? C11 C12 1.482(4) . ? C11 C3 1.617(4) . ? C11 H11 0.98 . ? C12 C13 1.340(4) . ? C12 H12 0.93 . ? C14 C13 1.497(4) . ? C15 H15A 0.96 . ? C15 H15B 0.96 . ? C15 H15C 0.96 . ? C16 C13 1.503(4) . ? C16 H16A 0.96 . ? C16 H16B 0.96 . ? C16 H16C 0.96 . ? C17 H17 0.93 . ? C18 C17 1.383(4) . ? C18 H18 0.93 . ? C19 C18 1.396(4) . ? C19 C20 1.387(3) . ? C19 C22 1.490(3) . ? C20 H20 0.93 . ? C21 C20 1.380(3) . ? C21 H21 0.93 . ? C22 C31 1.387(4) . ? C23 C22 1.438(4) . ? C23 C24 1.443(3) . ? C23 C28 1.432(3) . ? C24 C25 1.385(3) . ? C24 C32 1.491(3) . ? C25 C26 1.402(4) . ? C25 H25 0.93 . ? C26 H26 0.93 . ? C27 C26 1.360(4) . ? C27 H27 0.93 . ? C28 C27 1.418(4) . ? C28 C29 1.411(4) . ? C29 C30 1.364(4) . ? C29 H29 0.93 . ? C30 H30 0.93 . ? C31 C30 1.393(4) . ? C31 H31 0.93 . ? C32 C36 1.388(3) . ? C33 C32 1.400(3) . ? C33 C34 1.373(3) . ? C33 H33 0.93 . ? C34 H34 0.93 . ? C35 H35 0.93 . ? C36 C35 1.377(3) . ? C36 H36 0.93 . ? C37 C38 1.382(4) . ? C37 H37 0.93 . ? C38 H38 0.93 . ? C39 C38 1.385(4) . ? C39 C40 1.380(3) . ? C40 C41 1.381(4) . ? C40 H40 0.93 . ? C41 H41 0.93 . ? C42 C39 1.489(3) . ? C42 C51 1.380(4) . ? C43 C42 1.438(3) . ? C43 C44 1.446(3) . ? C43 C48 1.434(3) . ? C44 C45 1.370(3) . ? C44 C52 1.494(3) . ? C45 C46 1.404(3) . ? C45 H45 0.93 . ? C46 C47 1.352(4) . ? C46 H46 0.93 . ? C47 H47 0.93 . ? C48 C47 1.412(3) . ? C48 C49 1.419(4) . ? C49 H49 0.93 . ? C50 C49 1.356(4) . ? C50 H50 0.93 . ? C51 C50 1.395(4) . ? C51 H51 0.93 . ? C52 C53 1.382(4) . ? C52 C56 1.388(3) . ? C53 C54 1.373(4) . ? C53 H53 0.93 . ? C54 H54 0.93 . ? C55 C56 1.374(4) . ? C55 H55 0.93 . ? C56 H56 0.93 . ? N1 C17 1.335(3) . ? N1 C21 1.344(3) . ? N2 C34 1.340(3) . ? N2 C35 1.338(3) . ? N3 C37 1.328(4) . ? N3 C41 1.331(3) . ? N4 C54 1.325(3) . ? N4 C55 1.325(3) . ? O1 C1 1.325(3) . ? O1 H1O 0.82 . ? O2 C1 1.209(3) . ? O3 C9 1.323(3) . ? O3 H3O 0.82 . ? O4 C9 1.216(3) . ? O5 C6 1.309(3) . ? O5 H5O 0.82 . ? O7 C14 1.313(3) . ? O7 H7O 0.82 . ? O8 C14 1.209(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C2 C10 116.3(2) . . ? C1 C2 C3 119.1(2) . . ? C1 C2 C7 105.7(2) . . ? C1 O1 H1O 109.5 . . ? C2 C3 C11 88.88(19) . . ? C2 C3 H3 109.9 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? C3 C11 H11 109.3 . . ? C3 C2 C10 90.7(2) . . ? C3 C4 H4 116.6 . . ? C4 C3 C11 114.2(2) . . ? C4 C3 C2 122.2(2) . . ? C4 C3 H3 109.9 . . ? C4 C5 C6 121.4(2) . . ? C4 C5 C8 121.6(3) . . ? C5 C4 C3 126.9(3) . . ? C5 C4 H4 116.6 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? C6 C5 C8 117.0(2) . . ? C6 O5 H5O 109.5 . . ? C7 C2 C10 114.2(2) . . ? C7 C2 C3 110.7(2) . . ? C9 C10 C11 113.3(2) . . ? C9 C10 C15 112.9(2) . . ? C9 C10 C2 108.1(2) . . ? C9 O3 H3O 109.5 . . ? C10 C11 C3 90.00(19) . . ? C10 C11 H11 109.3 . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? C11 C10 C2 89.32(19) . . ? C11 C12 H12 115.2 . . ? C11 C3 H3 109.9 . . ? C12 C11 C10 120.5(2) . . ? C12 C11 C3 117.1(2) . . ? C12 C11 H11 109.3 . . ? C12 C13 C14 122.5(2) . . ? C12 C13 C16 121.4(2) . . ? C13 C12 C11 129.6(2) . . ? C13 C12 H12 115.2 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? C14 C13 C16 116.2(2) . . ? C14 O7 H7O 109.5 . . ? C15 C10 C11 113.4(2) . . ? C15 C10 C2 117.8(2) . . ? C17 C18 C19 119.5(2) . . ? C17 C18 H18 120.3 . . ? C17 N1 C21 116.8(2) . . ? C18 C17 H17 118.2 . . ? C18 C19 C22 119.7(2) . . ? C19 C18 H18 120.3 . . ? C19 C20 H20 120.1 . . ? C20 C19 C18 116.8(2) . . ? C20 C19 C22 123.5(2) . . ? C20 C21 H21 118.4 . . ? C21 C20 C19 119.8(2) . . ? C21 C20 H20 120.1 . . ? C22 C23 C24 125.7(2) . . ? C22 C31 C30 122.1(3) . . ? C22 C31 H31 118.9 . . ? C23 C22 C19 125.3(2) . . ? C23 C24 C32 125.6(2) . . ? C24 C25 C26 122.4(2) . . ? C24 C25 H25 118.8 . . ? C25 C24 C23 119.7(2) . . ? C25 C24 C32 114.5(2) . . ? C25 C26 H26 120.5 . . ? C26 C25 H25 118.8 . . ? C26 C27 C28 121.4(2) . . ? C26 C27 H27 119.3 . . ? C27 C26 C25 119.0(3) . . ? C27 C26 H26 120.5 . . ? C27 C28 C23 120.4(2) . . ? C28 C23 C22 117.3(2) . . ? C28 C23 C24 116.9(2) . . ? C28 C27 H27 119.3 . . ? C28 C29 H29 119.6 . . ? C29 C28 C23 120.4(2) . . ? C29 C28 C27 119.1(2) . . ? C29 C30 C31 119.7(3) . . ? C29 C30 H30 120.1 . . ? C30 C29 C28 120.9(2) . . ? C30 C29 H29 119.6 . . ? C30 C31 H31 118.9 . . ? C31 C22 C19 115.2(2) . . ? C31 C22 C23 119.5(2) . . ? C31 C30 H30 120.1 . . ? C32 C33 H33 120.2 . . ? C32 C36 H36 120.1 . . ? C33 C32 C24 120.8(2) . . ? C33 C34 H34 118.5 . . ? C34 C33 C32 119.7(2) . . ? C34 C33 H33 120.2 . . ? C35 C36 C32 119.9(2) . . ? C35 C36 H36 120.1 . . ? C35 N2 C34 117.4(2) . . ? C36 C32 C24 122.2(2) . . ? C36 C32 C33 116.8(2) . . ? C36 C35 H35 118.5 . . ? C37 C38 C39 119.3(3) . . ? C37 C38 H38 120.4 . . ? C37 N3 C41 115.9(2) . . ? C38 C37 H37 117.8 . . ? C38 C39 C42 120.5(2) . . ? C39 C38 H38 120.4 . . ? C39 C40 C41 119.9(2) . . ? C39 C40 H40 120 . . ? C40 C39 C38 116.6(2) . . ? C40 C39 C42 122.8(2) . . ? C40 C41 H41 118.1 . . ? C41 C40 H40 120 . . ? C42 C43 C44 126.0(2) . . ? C42 C51 C50 122.4(2) . . ? C42 C51 H51 118.8 . . ? C43 C42 C39 125.0(2) . . ? C43 C44 C52 124.9(2) . . ? C44 C45 C46 122.3(2) . . ? C44 C45 H45 118.8 . . ? C45 C44 C43 119.6(2) . . ? C45 C44 C52 115.5(2) . . ? C45 C46 H46 120.2 . . ? C46 C45 H45 118.8 . . ? C46 C47 C48 121.0(2) . . ? C46 C47 H47 119.5 . . ? C47 C46 C45 119.6(2) . . ? C47 C46 H46 120.2 . . ? C47 C48 C43 120.4(2) . . ? C47 C48 C49 119.4(2) . . ? C48 C43 C42 117.2(2) . . ? C48 C43 C44 116.9(2) . . ? C48 C47 H47 119.5 . . ? C48 C49 H49 119.5 . . ? C49 C48 C43 120.2(2) . . ? C49 C50 C51 119.6(2) . . ? C49 C50 H50 120.2 . . ? C50 C49 C48 120.9(2) . . ? C50 C49 H49 119.5 . . ? C50 C51 H51 118.8 . . ? C51 C42 C39 115.5(2) . . ? C51 C42 C43 119.5(2) . . ? C51 C50 H50 120.2 . . ? C52 C53 H53 119.9 . . ? C52 C56 H56 120 . . ? C53 C52 C44 122.7(2) . . ? C53 C52 C56 115.7(2) . . ? C53 C54 H54 118 . . ? C54 C53 C52 120.2(3) . . ? C54 C53 H53 119.9 . . ? C55 C56 C52 119.9(2) . . ? C55 C56 H56 120 . . ? C55 N4 C54 115.9(2) . . ? C56 C52 C44 121.4(2) . . ? C56 C55 H55 117.9 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N1 C17 C18 123.5(3) . . ? N1 C17 H17 118.2 . . ? N1 C21 C20 123.3(2) . . ? N1 C21 H21 118.4 . . ? N2 C34 C33 123.1(2) . . ? N2 C34 H34 118.5 . . ? N2 C35 C36 123.1(2) . . ? N2 C35 H35 118.5 . . ? N3 C37 C38 124.4(3) . . ? N3 C37 H37 117.8 . . ? N3 C41 C40 123.8(2) . . ? N3 C41 H41 118.1 . . ? N4 C54 C53 124.0(3) . . ? N4 C54 H54 118 . . ? N4 C55 C56 124.1(3) . . ? N4 C55 H55 117.9 . . ? O1 C1 C2 111.2(2) . . ? O2 C1 C2 125.2(2) . . ? O2 C1 O1 123.5(3) . . ? O3 C9 C10 114.5(2) . . ? O4 C9 C10 122.2(2) . . ? O4 C9 O3 123.2(2) . . ? O5 C6 C5 114.8(2) . . ? O6 C6 C5 124.9(3) . . ? O6 C6 O5 120.3(3) . . ? O7 C14 C13 111.9(2) . . ? O8 C14 C13 124.8(2) . . ? O8 C14 O7 123.2(2) . . ?