# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_suman _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H24 N2 O5' _chemical_formula_sum 'C13 H24 N2 O5' _chemical_formula_weight 288.34 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 16.1814(15) _cell_length_b 10.4831(9) _cell_length_c 18.8326(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3194.6(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5313 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 24.87 _exptl_crystal_description niddle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.426 _exptl_crystal_size_mid 0.274 _exptl_crystal_size_min 0.153 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 20302 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 24.93 _reflns_number_total 2745 _reflns_number_gt 2013 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0223P)^2^+2.1322P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0014(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2745 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1142 _refine_ls_wR_factor_gt 0.1045 _refine_ls_goodness_of_fit_ref 1.271 _refine_ls_restrained_S_all 1.271 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 O5 O 0.80474(11) 0.86825(18) 0.83117(10) 0.0504(5) Uani 1 1 d . . . O4 O 0.82381(11) 0.97248(17) 0.93234(10) 0.0479(5) Uani 1 1 d . . . O3 O 0.80353(10) 0.61939(16) 0.90893(10) 0.0466(5) Uani 1 1 d . . . O1 O 0.79619(10) 0.10383(17) 0.70509(9) 0.0435(5) Uani 1 1 d . . . N2 N 0.92336(11) 0.69317(17) 0.86579(10) 0.0337(5) Uani 1 1 d . . . H2 H 0.9647 0.6781 0.8383 0.040 Uiso 1 1 calc R . . C1 C 0.7055(2) 0.0033(4) 0.62824(18) 0.0780(11) Uani 1 1 d . . . H1A H 0.6831 -0.0460 0.6666 0.117 Uiso 1 1 calc R . . H1B H 0.6976 -0.0417 0.5844 0.117 Uiso 1 1 calc R . . H1C H 0.6778 0.0842 0.6259 0.117 Uiso 1 1 calc R . . C2 C 0.79678(17) 0.0246(3) 0.64048(13) 0.0478(7) Uani 1 1 d . . . C5 C 0.86661(14) 0.1395(2) 0.73640(13) 0.0343(6) Uani 1 1 d . . . N1 N 0.85185(12) 0.20922(19) 0.79380(11) 0.0429(5) Uani 1 1 d . . . H4 H 0.8017 0.2301 0.8035 0.051 Uiso 1 1 calc R . . C6 C 0.91720(16) 0.2511(2) 0.84045(15) 0.0487(7) Uani 1 1 d . . . H21 H 0.9670 0.2654 0.8129 0.058 Uiso 1 1 calc R . . H20 H 0.9288 0.1845 0.8748 0.058 Uiso 1 1 calc R . . C7 C 0.89475(16) 0.3722(2) 0.87923(13) 0.0417(6) Uani 1 1 d . . . H6A H 0.9390 0.3939 0.9118 0.050 Uiso 1 1 calc R . . H6B H 0.8453 0.3574 0.9071 0.050 Uiso 1 1 calc R . . C8 C 0.87977(15) 0.4843(2) 0.82962(13) 0.0357(6) Uani 1 1 d . . . H7A H 0.9273 0.4953 0.7988 0.043 Uiso 1 1 calc R . . H7B H 0.8321 0.4667 0.8000 0.043 Uiso 1 1 calc R . . C9 C 0.86530(14) 0.6044(2) 0.87090(12) 0.0334(5) Uani 1 1 d . . . C10 C 0.92198(13) 0.8147(2) 0.90357(13) 0.0339(6) Uani 1 1 d . . . C13 C 0.84275(14) 0.8853(2) 0.88474(13) 0.0320(5) Uani 1 1 d . . . O2 O 0.93532(10) 0.11244(18) 0.71557(10) 0.0516(5) Uani 1 1 d . . . C3 C 0.8344(2) 0.0975(4) 0.57967(16) 0.0802(11) Uani 1 1 d . . . H12A H 0.8080 0.1792 0.5757 0.120 Uiso 1 1 calc R . . H12B H 0.8267 0.0505 0.5364 0.120 Uiso 1 1 calc R . . H12C H 0.8924 0.1092 0.5882 0.120 Uiso 1 1 calc R . . C4 C 0.8397(2) -0.1001(3) 0.65444(17) 0.0707(9) Uani 1 1 d . . . H13A H 0.8979 -0.0854 0.6601 0.106 Uiso 1 1 calc R . . H13B H 0.8308 -0.1568 0.6152 0.106 Uiso 1 1 calc R . . H13C H 0.8179 -0.1377 0.6970 0.106 Uiso 1 1 calc R . . C11 C 0.93213(18) 0.7937(3) 0.98271(15) 0.0567(8) Uani 1 1 d . . . H14A H 0.8869 0.7433 1.0001 0.085 Uiso 1 1 calc R . . H14B H 0.9327 0.8746 1.0066 0.085 Uiso 1 1 calc R . . H14C H 0.9832 0.7499 0.9915 0.085 Uiso 1 1 calc R . . C12 C 0.99292(16) 0.8945(2) 0.87361(19) 0.0618(9) Uani 1 1 d . . . H15A H 1.0442 0.8502 0.8807 0.093 Uiso 1 1 calc R . . H15B H 0.9949 0.9752 0.8976 0.093 Uiso 1 1 calc R . . H15C H 0.9843 0.9081 0.8238 0.093 Uiso 1 1 calc R . . H22 H 0.780(2) 1.015(3) 0.9189(17) 0.082(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O5 0.0475(11) 0.0564(12) 0.0475(11) -0.0102(9) -0.0131(9) 0.0168(9) O4 0.0432(11) 0.0458(11) 0.0546(11) -0.0150(9) -0.0114(9) 0.0186(9) O3 0.0370(10) 0.0368(10) 0.0660(12) -0.0149(9) 0.0188(9) -0.0114(8) O1 0.0335(9) 0.0482(11) 0.0489(10) -0.0145(9) 0.0004(8) -0.0042(8) N2 0.0242(10) 0.0268(10) 0.0503(12) -0.0041(9) 0.0074(9) -0.0016(8) C1 0.064(2) 0.103(3) 0.067(2) -0.022(2) -0.0097(17) -0.027(2) C2 0.0550(17) 0.0510(16) 0.0372(14) -0.0090(13) 0.0031(12) -0.0146(14) C5 0.0313(13) 0.0271(12) 0.0444(14) -0.0005(11) 0.0060(11) -0.0029(10) N1 0.0288(11) 0.0393(12) 0.0606(14) -0.0213(11) 0.0013(10) 0.0008(9) C6 0.0439(15) 0.0347(14) 0.0673(18) -0.0127(13) -0.0134(13) 0.0063(12) C7 0.0447(14) 0.0342(14) 0.0464(15) -0.0081(12) -0.0093(12) 0.0012(11) C8 0.0346(13) 0.0311(13) 0.0413(14) -0.0072(11) 0.0046(11) -0.0048(10) C9 0.0290(12) 0.0276(12) 0.0435(14) -0.0026(11) 0.0016(11) -0.0019(10) C10 0.0260(12) 0.0231(12) 0.0526(15) -0.0051(11) -0.0032(11) -0.0006(10) C13 0.0294(12) 0.0279(12) 0.0388(13) -0.0010(11) 0.0003(11) -0.0019(10) O2 0.0327(10) 0.0623(13) 0.0597(12) -0.0141(10) 0.0135(9) -0.0019(9) C3 0.102(3) 0.093(3) 0.0453(17) 0.0052(18) 0.0038(18) -0.036(2) C4 0.096(3) 0.0527(19) 0.063(2) -0.0199(16) 0.0052(18) -0.0017(18) C11 0.0631(19) 0.0476(17) 0.0594(18) -0.0078(14) -0.0248(15) 0.0146(14) C12 0.0342(15) 0.0339(15) 0.117(3) -0.0081(17) 0.0093(16) -0.0093(12) _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 O5 C13 1.195(3) . ? O4 C13 1.316(3) . ? O4 H22 0.88(3) . ? O3 C9 1.240(3) . ? O1 C5 1.336(3) . ? O1 C2 1.474(3) . ? N2 C9 1.326(3) . ? N2 C10 1.459(3) . ? N2 H2 0.8600 . ? C1 C2 1.511(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C4 1.503(4) . ? C2 C3 1.505(4) . ? C5 O2 1.213(3) . ? C5 N1 1.327(3) . ? N1 C6 1.443(3) . ? N1 H4 0.8600 . ? C6 C7 1.509(3) . ? C6 H21 0.9700 . ? C6 H20 0.9700 . ? C7 C8 1.520(3) . ? C7 H6A 0.9700 . ? C7 H6B 0.9700 . ? C8 C9 1.499(3) . ? C8 H7A 0.9700 . ? C8 H7B 0.9700 . ? C10 C11 1.516(4) . ? C10 C13 1.522(3) . ? C10 C12 1.528(3) . ? C3 H12A 0.9600 . ? C3 H12B 0.9600 . ? C3 H12C 0.9600 . ? C4 H13A 0.9600 . ? C4 H13B 0.9600 . ? C4 H13C 0.9600 . ? C11 H14A 0.9600 . ? C11 H14B 0.9600 . ? C11 H14C 0.9600 . ? C12 H15A 0.9600 . ? C12 H15B 0.9600 . ? C12 H15C 0.9600 . ? 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 C13 O4 H22 110(2) . . ? C5 O1 C2 121.12(19) . . ? C9 N2 C10 124.50(19) . . ? C9 N2 H2 117.8 . . ? C10 N2 H2 117.8 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C4 110.4(2) . . ? O1 C2 C3 110.1(2) . . ? C4 C2 C3 112.8(3) . . ? O1 C2 C1 101.7(2) . . ? C4 C2 C1 110.5(3) . . ? C3 C2 C1 110.7(3) . . ? O2 C5 N1 123.9(2) . . ? O2 C5 O1 125.0(2) . . ? N1 C5 O1 111.12(19) . . ? C5 N1 C6 122.1(2) . . ? C5 N1 H4 118.9 . . ? C6 N1 H4 118.9 . . ? N1 C6 C7 112.0(2) . . ? N1 C6 H21 109.2 . . ? C7 C6 H21 109.2 . . ? N1 C6 H20 109.2 . . ? C7 C6 H20 109.2 . . ? H21 C6 H20 107.9 . . ? C6 C7 C8 113.0(2) . . ? C6 C7 H6A 109.0 . . ? C8 C7 H6A 109.0 . . ? C6 C7 H6B 109.0 . . ? C8 C7 H6B 109.0 . . ? H6A C7 H6B 107.8 . . ? C9 C8 C7 110.82(19) . . ? C9 C8 H7A 109.5 . . ? C7 C8 H7A 109.5 . . ? C9 C8 H7B 109.5 . . ? C7 C8 H7B 109.5 . . ? H7A C8 H7B 108.1 . . ? O3 C9 N2 121.6(2) . . ? O3 C9 C8 122.1(2) . . ? N2 C9 C8 116.2(2) . . ? N2 C10 C11 110.6(2) . . ? N2 C10 C13 108.90(18) . . ? C11 C10 C13 113.0(2) . . ? N2 C10 C12 106.6(2) . . ? C11 C10 C12 111.2(2) . . ? C13 C10 C12 106.3(2) . . ? O5 C13 O4 124.0(2) . . ? O5 C13 C10 123.9(2) . . ? O4 C13 C10 112.0(2) . . ? C2 C3 H12A 109.5 . . ? C2 C3 H12B 109.5 . . ? H12A C3 H12B 109.5 . . ? C2 C3 H12C 109.5 . . ? H12A C3 H12C 109.5 . . ? H12B C3 H12C 109.5 . . ? C2 C4 H13A 109.5 . . ? C2 C4 H13B 109.5 . . ? H13A C4 H13B 109.5 . . ? C2 C4 H13C 109.5 . . ? H13A C4 H13C 109.5 . . ? H13B C4 H13C 109.5 . . ? C10 C11 H14A 109.5 . . ? C10 C11 H14B 109.5 . . ? H14A C11 H14B 109.5 . . ? C10 C11 H14C 109.5 . . ? H14A C11 H14C 109.5 . . ? H14B C11 H14C 109.5 . . ? C10 C12 H15A 109.5 . . ? C10 C12 H15B 109.5 . . ? H15A C12 H15B 109.5 . . ? C10 C12 H15C 109.5 . . ? H15A C12 H15C 109.5 . . ? H15B C12 H15C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 24.93 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.173 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.035 _database_code_depnum_ccdc_archive 'CCDC 912836' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mo_dh_skm_062a_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H26 N2 O5' _chemical_formula_sum 'C18 H26 N2 O5' _chemical_formula_weight 350.41 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 9.4323(10) _cell_length_b 19.848(2) _cell_length_c 20.122(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3767.1(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4653 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 24.92 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.481 _exptl_crystal_size_mid 0.362 _exptl_crystal_size_min 0.282 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.962 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24641 _diffrn_reflns_av_R_equivalents 0.0580 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.08 _reflns_number_total 3343 _reflns_number_gt 2552 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0335P)^2^+5.6789P] 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_extinction_coef ? _refine_ls_number_reflns 3343 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0778 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1370 _refine_ls_wR_factor_gt 0.1270 _refine_ls_goodness_of_fit_ref 1.163 _refine_ls_restrained_S_all 1.163 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0311(2) 0.81385(9) 0.64963(9) 0.0250(5) Uani 1 1 d . . . O2 O 0.0044(2) 1.14498(9) 0.70776(9) 0.0272(5) Uani 1 1 d . . . O3 O -0.1986(2) 0.82600(10) 0.68684(10) 0.0297(5) Uani 1 1 d . . . O4 O -0.0958(2) 1.00701(9) 0.73043(8) 0.0221(4) Uani 1 1 d . . . O5 O -0.0803(2) 1.11848(9) 0.60688(9) 0.0261(5) Uani 1 1 d . . . N1 N -0.0085(3) 0.85459(11) 0.75012(12) 0.0259(5) Uani 1 1 d . . . H1 H 0.0825 0.8567 0.7522 0.031 Uiso 1 1 calc R . . N2 N 0.1363(2) 1.02543(11) 0.71686(10) 0.0185(5) Uani 1 1 d . . . H2 H 0.2204 1.0215 0.7329 0.022 Uiso 1 1 calc R . . C1 C -0.0745(4) 0.71629(14) 0.59436(15) 0.0344(8) Uani 1 1 d . . . H1A H -0.0163 0.6895 0.6232 0.052 Uiso 1 1 calc R . . H1B H -0.0831 0.6944 0.5520 0.052 Uiso 1 1 calc R . . H1C H -0.1669 0.7215 0.6138 0.052 Uiso 1 1 calc R . . C2 C -0.0075(3) 0.78475(14) 0.58509(13) 0.0251(6) Uani 1 1 d . . . C3 C -0.0710(3) 0.83093(13) 0.69464(13) 0.0238(6) Uani 1 1 d . . . C4 C -0.0920(3) 0.87642(14) 0.80600(13) 0.0260(7) Uani 1 1 d . . . H4A H -0.1211 0.8377 0.8320 0.031 Uiso 1 1 calc R . . H4B H -0.1766 0.8992 0.7904 0.031 Uiso 1 1 calc R . . C5 C -0.0061(3) 0.92350(13) 0.84862(13) 0.0214(6) Uani 1 1 d . . . C6 C 0.0566(3) 0.98188(13) 0.82240(12) 0.0186(6) Uani 1 1 d . . . C7 C 0.0263(3) 1.00454(12) 0.75275(13) 0.0186(6) Uani 1 1 d . . . C8 C 0.1177(3) 1.05506(13) 0.65061(12) 0.0207(6) Uani 1 1 d . . . C9 C 0.0001(3) 1.10795(13) 0.65214(13) 0.0214(6) Uani 1 1 d . . . C10 C -0.1045(4) 1.19602(14) 0.71228(15) 0.0340(8) Uani 1 1 d . . . H10A H -0.0936 1.2275 0.6765 0.051 Uiso 1 1 calc R . . H10B H -0.0961 1.2193 0.7539 0.051 Uiso 1 1 calc R . . H10C H -0.1961 1.1751 0.7095 0.051 Uiso 1 1 calc R . . C11 C -0.0994(4) 0.83276(15) 0.54562(14) 0.0349(8) Uani 1 1 d . . . H11A H -0.1892 0.8380 0.5675 0.052 Uiso 1 1 calc R . . H11B H -0.1141 0.8150 0.5018 0.052 Uiso 1 1 calc R . . H11C H -0.0532 0.8758 0.5426 0.052 Uiso 1 1 calc R . . C12 C 0.1367(4) 0.77832(17) 0.55226(15) 0.0398(8) Uani 1 1 d . . . H12A H 0.1778 0.8223 0.5470 0.060 Uiso 1 1 calc R . . H12B H 0.1261 0.7575 0.5095 0.060 Uiso 1 1 calc R . . H12C H 0.1975 0.7511 0.5796 0.060 Uiso 1 1 calc R . . C13 C 0.0182(3) 0.90825(15) 0.91520(13) 0.0300(7) Uani 1 1 d . . . H13 H -0.0221 0.8697 0.9334 0.036 Uiso 1 1 calc R . . C14 C 0.1011(3) 0.94927(16) 0.95467(14) 0.0330(8) Uani 1 1 d . . . H14 H 0.1147 0.9384 0.9992 0.040 Uiso 1 1 calc R . . C15 C 0.1636(3) 1.00609(16) 0.92872(14) 0.0300(7) Uani 1 1 d . . . H15 H 0.2203 1.0334 0.9553 0.036 Uiso 1 1 calc R . . C16 C 0.1412(3) 1.02222(14) 0.86265(13) 0.0229(6) Uani 1 1 d . . . H16 H 0.1833 1.0606 0.8449 0.027 Uiso 1 1 calc R . . C17 C 0.2538(3) 1.09126(15) 0.63224(13) 0.0275(7) Uani 1 1 d . . . H17A H 0.2755 1.1243 0.6656 0.041 Uiso 1 1 calc R . . H17B H 0.2422 1.1132 0.5901 0.041 Uiso 1 1 calc R . . H17C H 0.3299 1.0592 0.6294 0.041 Uiso 1 1 calc R . . C18 C 0.0822(3) 1.00036(14) 0.60000(13) 0.0275(7) Uani 1 1 d . . . H18A H 0.1584 0.9684 0.5981 0.041 Uiso 1 1 calc R . . H18B H 0.0693 1.0205 0.5570 0.041 Uiso 1 1 calc R . . H18C H -0.0035 0.9779 0.6131 0.041 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0243(11) 0.0282(10) 0.0225(10) -0.0050(8) -0.0011(9) 0.0035(9) O2 0.0307(12) 0.0249(10) 0.0261(10) -0.0026(8) -0.0066(9) 0.0047(9) O3 0.0229(13) 0.0318(11) 0.0342(11) -0.0028(9) 0.0003(9) -0.0004(9) O4 0.0135(10) 0.0332(11) 0.0197(9) 0.0028(8) -0.0005(8) 0.0031(8) O5 0.0254(12) 0.0304(10) 0.0224(10) 0.0042(8) -0.0042(9) 0.0060(9) N1 0.0211(14) 0.0301(12) 0.0266(12) -0.0027(10) 0.0019(11) 0.0006(11) N2 0.0112(12) 0.0273(11) 0.0172(11) 0.0048(9) -0.0016(9) 0.0038(10) C1 0.041(2) 0.0283(15) 0.0340(16) -0.0045(13) 0.0025(15) -0.0016(15) C2 0.0262(17) 0.0268(14) 0.0222(14) -0.0035(11) -0.0020(13) -0.0002(13) C3 0.0263(18) 0.0188(13) 0.0264(15) 0.0008(11) 0.0024(13) 0.0022(12) C4 0.0274(17) 0.0273(14) 0.0232(14) 0.0035(11) 0.0070(13) 0.0002(13) C5 0.0178(15) 0.0263(14) 0.0201(13) -0.0001(11) 0.0040(12) 0.0075(12) C6 0.0146(15) 0.0242(13) 0.0172(12) 0.0004(10) 0.0027(11) 0.0072(11) C7 0.0193(15) 0.0182(12) 0.0183(12) -0.0016(10) 0.0007(12) 0.0036(12) C8 0.0189(16) 0.0264(14) 0.0169(13) 0.0055(11) -0.0009(11) 0.0026(12) C9 0.0233(16) 0.0228(13) 0.0180(13) 0.0037(11) 0.0006(12) -0.0024(12) C10 0.043(2) 0.0205(14) 0.0384(17) -0.0026(12) -0.0027(15) 0.0137(14) C11 0.045(2) 0.0312(16) 0.0284(15) 0.0017(13) -0.0064(15) 0.0007(15) C12 0.037(2) 0.0489(19) 0.0332(17) -0.0105(15) 0.0067(16) 0.0009(17) C13 0.0311(18) 0.0357(16) 0.0233(14) 0.0078(12) 0.0093(13) 0.0103(14) C14 0.0328(19) 0.0509(19) 0.0154(13) 0.0005(13) 0.0007(13) 0.0174(16) C15 0.0236(17) 0.0444(18) 0.0221(14) -0.0074(13) -0.0005(13) 0.0066(14) C16 0.0162(15) 0.0320(15) 0.0205(13) -0.0013(11) 0.0020(12) 0.0066(12) C17 0.0234(17) 0.0360(16) 0.0231(14) 0.0084(12) 0.0014(13) 0.0013(14) C18 0.0308(18) 0.0294(15) 0.0223(14) -0.0005(12) 0.0009(13) 0.0075(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C3 1.365(3) . ? O1 C2 1.467(3) . ? O2 C9 1.340(3) . ? O2 C10 1.446(3) . ? O3 C3 1.218(4) . ? O4 C7 1.237(3) . ? O5 C9 1.203(3) . ? N1 C3 1.347(4) . ? N1 C4 1.440(4) . ? N1 H1 0.8600 . ? N2 C7 1.331(3) . ? N2 C8 1.468(3) . ? N2 H2 0.8600 . ? C1 C2 1.510(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C11 1.513(4) . ? C2 C12 1.518(4) . ? C4 C5 1.505(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C13 1.393(4) . ? C5 C6 1.404(4) . ? C6 C16 1.391(4) . ? C6 C7 1.500(4) . ? C8 C17 1.517(4) . ? C8 C18 1.526(4) . ? C8 C9 1.528(4) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.380(4) . ? C13 H13 0.9300 . ? C14 C15 1.376(4) . ? C14 H14 0.9300 . ? C15 C16 1.384(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 C3 O1 C2 120.7(2) . . ? C9 O2 C10 114.5(2) . . ? C3 N1 C4 120.8(3) . . ? C3 N1 H1 119.6 . . ? C4 N1 H1 119.6 . . ? C7 N2 C8 121.7(2) . . ? C7 N2 H2 119.2 . . ? C8 N2 H2 119.2 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C1 110.4(2) . . ? O1 C2 C11 111.0(2) . . ? C1 C2 C11 113.1(3) . . ? O1 C2 C12 101.3(2) . . ? C1 C2 C12 110.7(3) . . ? C11 C2 C12 109.7(3) . . ? O3 C3 N1 124.6(3) . . ? O3 C3 O1 126.3(3) . . ? N1 C3 O1 109.1(3) . . ? N1 C4 C5 109.7(2) . . ? N1 C4 H4A 109.7 . . ? C5 C4 H4A 109.7 . . ? N1 C4 H4B 109.7 . . ? C5 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? C13 C5 C6 118.1(3) . . ? C13 C5 C4 120.1(3) . . ? C6 C5 C4 121.7(2) . . ? C16 C6 C5 119.9(2) . . ? C16 C6 C7 118.8(2) . . ? C5 C6 C7 121.2(2) . . ? O4 C7 N2 121.1(2) . . ? O4 C7 C6 121.9(2) . . ? N2 C7 C6 116.9(2) . . ? N2 C8 C17 108.1(2) . . ? N2 C8 C18 110.3(2) . . ? C17 C8 C18 111.1(2) . . ? N2 C8 C9 110.1(2) . . ? C17 C8 C9 107.1(2) . . ? C18 C8 C9 110.0(2) . . ? O5 C9 O2 123.8(3) . . ? O5 C9 C8 124.2(2) . . ? O2 C9 C8 111.8(2) . . ? O2 C10 H10A 109.5 . . ? O2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C2 C11 H11A 109.5 . . ? C2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C2 C12 H12A 109.5 . . ? C2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C5 121.3(3) . . ? C14 C13 H13 119.4 . . ? C5 C13 H13 119.4 . . ? C15 C14 C13 120.5(3) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 119.3(3) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C15 C16 C6 120.9(3) . . ? C15 C16 H16 119.5 . . ? C6 C16 H16 119.5 . . ? C8 C17 H17A 109.5 . . ? C8 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C8 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C8 C18 H18A 109.5 . . ? C8 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C8 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.08 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.410 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.055 _database_code_depnum_ccdc_archive 'CCDC 912835' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_bn #TrackingRef 'web_deposit_cif_file_2_DebasishHaldar_1354020949.maba-aib.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C16 H22 N2 O5), C4 H8 O2' _chemical_formula_sum 'C36 H52 N4 O12' _chemical_formula_weight 732.82 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.864(3) _cell_length_b 11.560(3) _cell_length_c 31.828(9) _cell_angle_alpha 90.032(5) _cell_angle_beta 90.091(5) _cell_angle_gamma 91.966(4) _cell_volume 3995(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9908 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 28.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.482 _exptl_crystal_size_mid 0.365 _exptl_crystal_size_min 0.281 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.961 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43036 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0799 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 0.64 _diffrn_reflns_theta_max 27.00 _reflns_number_total 15392 _reflns_number_gt 10347 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1255P)^2^+31.5103P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 15392 _refine_ls_number_parameters 965 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1623 _refine_ls_R_factor_gt 0.1255 _refine_ls_wR_factor_ref 0.3793 _refine_ls_wR_factor_gt 0.3577 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.138 _refine_ls_shift/su_max 0.20 _refine_ls_shift/su_mean 0.007 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 O5 O 0.4401(5) 0.8053(4) 1.03117(15) 0.0348(13) Uani 1 1 d . . . O4 O 0.6003(5) 0.9266(4) 1.02884(16) 0.0365(13) Uani 1 1 d . . . H4 H 0.5918 0.9403 1.0539 0.055 Uiso 1 1 calc R . . O2 O 1.0507(5) 0.7583(4) 0.86989(14) 0.0252(10) Uani 1 1 d . . . O3 O 0.5420(5) 0.9020(4) 0.94082(16) 0.0343(12) Uani 1 1 d . . . O6 O 0.8584(5) 0.3182(4) 0.70859(13) 0.0236(10) Uani 1 1 d . . . O10 O 0.8973(4) -0.0839(4) 0.46837(13) 0.0215(9) Uani 1 1 d . . . H6 H 0.9407 -0.0356 0.4560 0.032 Uiso 1 1 calc R . . O9 O 1.0663(4) -0.1887(4) 0.46480(13) 0.0235(10) Uani 1 1 d . . . O8 O 0.9748(4) -0.0985(3) 0.55849(13) 0.0198(9) Uani 1 1 d . . . O7 O 0.6736(5) 0.2207(4) 0.71325(13) 0.0242(10) Uani 1 1 d . . . O19 O 0.1019(4) 0.5833(4) -0.03143(13) 0.0218(9) Uani 1 1 d . . . H19 H 0.0747 0.5527 -0.0529 0.033 Uiso 1 1 calc R . . O20 O -0.0672(4) 0.6882(4) -0.03525(13) 0.0231(10) Uani 1 1 d . . . O18 O 0.0259(4) 0.5983(4) 0.05851(13) 0.0198(9) Uani 1 1 d . . . O17 O 0.3256(5) 0.2786(4) 0.21331(13) 0.0252(10) Uani 1 1 d . . . O14 O 0.5606(5) 0.6943(4) 0.53122(15) 0.0345(12) Uani 1 1 d . . . O15 O 0.4001(6) 0.5735(5) 0.52887(16) 0.0375(13) Uani 1 1 d . . . H15 H 0.4343 0.5433 0.5488 0.056 Uiso 1 1 calc R . . O13 O 0.4584(5) 0.5973(4) 0.44095(16) 0.0336(12) Uani 1 1 d . . . O12 O -0.0506(4) 0.7417(4) 0.36991(14) 0.0242(10) Uani 1 1 d . . . O22 O 0.6714(7) 0.7223(6) 0.1439(2) 0.0552(17) Uani 1 1 d . . . O21 O 0.8329(8) 0.8227(6) 0.1698(2) 0.069(2) Uani 1 1 d . . . O23 O 0.6706(6) 0.2223(5) 0.3561(2) 0.0532(16) Uani 1 1 d . . . O24 O 0.8305(7) 0.3221(6) 0.3304(2) 0.066(2) Uani 1 1 d . . . O1 O 1.2135(5) 0.8645(4) 0.84242(17) 0.0365(12) Uani 1 1 d . . . N8 N 0.6974(6) 0.7989(5) 0.96487(17) 0.0275(13) Uani 1 1 d . . . H2 H 0.7740 0.7828 0.9633 0.033 Uiso 1 1 calc R . . N6 N 0.8135(5) -0.2077(4) 0.53441(15) 0.0200(11) Uani 1 1 d . . . H3 H 0.7363 -0.2260 0.5361 0.024 Uiso 1 1 calc R . . O16 O 0.1411(5) 0.1816(4) 0.20848(13) 0.0237(10) Uani 1 1 d . . . N2 N 0.1860(5) 0.7080(4) 0.03446(15) 0.0209(11) Uani 1 1 d . . . H5 H 0.2632 0.7267 0.0362 0.025 Uiso 1 1 calc R . . O11 O -0.2131(5) 0.6354(4) 0.34244(18) 0.0376(13) Uani 1 1 d . . . N4 N 0.3019(6) 0.7003(5) 0.46495(17) 0.0280(13) Uani 1 1 d . . . H7 H 0.2250 0.7154 0.4636 0.034 Uiso 1 1 calc R . . C12 C 1.2110(10) 0.6908(8) 0.7978(3) 0.051(2) Uani 1 1 d . . . H1A H 1.1382 0.6582 0.8109 0.076 Uiso 1 1 calc R . . H1B H 1.2608 0.6296 0.7878 0.076 Uiso 1 1 calc R . . H1C H 1.1880 0.7386 0.7747 0.076 Uiso 1 1 calc R . . C14 C 1.2836(8) 0.7633(8) 0.8296(3) 0.043(2) Uani 1 1 d . . . C16 C 1.1020(6) 0.8509(5) 0.85971(19) 0.0208(13) Uani 1 1 d . . . N7 N 1.0548(6) 0.9568(5) 0.86499(16) 0.0246(12) Uani 1 1 d . . . H103 H 1.1046 1.0150 0.8607 0.030 Uiso 1 1 calc R . . C10 C 0.9353(6) 0.9828(5) 0.87653(18) 0.0209(13) Uani 1 1 d . . . C11 C 0.8578(6) 0.9113(5) 0.90161(17) 0.0183(12) Uani 1 1 d . . . H6A H 0.8852 0.8413 0.9117 0.022 Uiso 1 1 calc R . . C6 C 0.7396(7) 0.9464(5) 0.91115(18) 0.0206(13) Uani 1 1 d . . . C5 C 0.6527(6) 0.8792(6) 0.93948(18) 0.0225(13) Uani 1 1 d . . . C4 C 0.6177(7) 0.7379(6) 0.9953(2) 0.0313(16) Uani 1 1 d . . . C2 C 0.5405(7) 0.8264(6) 1.0192(2) 0.0282(15) Uani 1 1 d . . . C9 C 0.8928(7) 1.0900(5) 0.86265(18) 0.0244(14) Uani 1 1 d . . . H11 H 0.9446 1.1394 0.8472 0.029 Uiso 1 1 calc R . . C8 C 0.7749(8) 1.1221(5) 0.87190(19) 0.0292(16) Uani 1 1 d . . . H12 H 0.7465 1.1918 0.8618 0.035 Uiso 1 1 calc R . . C7 C 0.6988(7) 1.0512(6) 0.89611(19) 0.0268(15) Uani 1 1 d . . . H13 H 0.6196 1.0738 0.9024 0.032 Uiso 1 1 calc R . . C13 C 1.3994(9) 0.8214(10) 0.8098(4) 0.063(3) Uani 1 1 d . . . H14A H 1.3756 0.8696 0.7868 0.095 Uiso 1 1 calc R . . H14B H 1.4526 0.7630 0.7997 0.095 Uiso 1 1 calc R . . H14C H 1.4421 0.8679 0.8306 0.095 Uiso 1 1 calc R . . C15 C 1.3194(9) 0.6959(9) 0.8688(3) 0.054(2) Uani 1 1 d . . . H15A H 1.3632 0.7467 0.8879 0.081 Uiso 1 1 calc R . . H15B H 1.3709 0.6337 0.8610 0.081 Uiso 1 1 calc R . . H15C H 1.2463 0.6649 0.8822 0.081 Uiso 1 1 calc R . . C1 C 0.6999(9) 0.6835(8) 1.0288(3) 0.047(2) Uani 1 1 d . . . H16A H 0.7521 0.6288 1.0157 0.070 Uiso 1 1 calc R . . H16B H 0.6491 0.6448 1.0495 0.070 Uiso 1 1 calc R . . H16C H 0.7497 0.7431 1.0422 0.070 Uiso 1 1 calc R . . C3 C 0.5306(9) 0.6512(7) 0.9728(3) 0.042(2) Uani 1 1 d . . . H17A H 0.4875 0.6901 0.9509 0.063 Uiso 1 1 calc R . . H17B H 0.4724 0.6188 0.9926 0.063 Uiso 1 1 calc R . . H17C H 0.5774 0.5905 0.9609 0.063 Uiso 1 1 calc R . . C18 C 0.8208(8) 0.3197(6) 0.7845(2) 0.0342(18) Uani 1 1 d . . . H18A H 0.7499 0.2683 0.7822 0.051 Uiso 1 1 calc R . . H18B H 0.8116 0.3692 0.8085 0.051 Uiso 1 1 calc R . . H18C H 0.8933 0.2754 0.7879 0.051 Uiso 1 1 calc R . . C17 C 0.8329(7) 0.3935(5) 0.74479(18) 0.0259(15) Uani 1 1 d . . . C21 C 0.7725(7) 0.2377(5) 0.69665(18) 0.0215(13) Uani 1 1 d . . . N5 N 0.8173(5) 0.1780(4) 0.66353(16) 0.0226(12) Uani 1 1 d . . . H21A H 0.8895 0.1990 0.6548 0.027 Uiso 1 1 calc R . . C22 C 0.7578(6) 0.0852(5) 0.64196(17) 0.0184(12) Uani 1 1 d . . . C25 C 0.8288(6) 0.0262(5) 0.61295(17) 0.0182(12) Uani 1 1 d . . . H23 H 0.9106 0.0497 0.6088 0.022 Uiso 1 1 calc R . . C26 C 0.7792(6) -0.0672(5) 0.59014(18) 0.0192(12) Uani 1 1 d . . . C28 C 0.8624(6) -0.1259(5) 0.55993(18) 0.0188(13) Uani 1 1 d . . . C29 C 0.8902(7) -0.2667(5) 0.50343(19) 0.0223(14) Uani 1 1 d . . . C32 C 0.9629(7) -0.1748(5) 0.47738(17) 0.0212(14) Uani 1 1 d . . . C27 C 0.6566(6) -0.1022(5) 0.59650(19) 0.0205(13) Uani 1 1 d . . . H28 H 0.6217 -0.1638 0.5813 0.025 Uiso 1 1 calc R . . C24 C 0.5873(7) -0.0444(6) 0.6256(2) 0.0254(14) Uani 1 1 d . . . H29 H 0.5061 -0.0690 0.6302 0.031 Uiso 1 1 calc R . . C23 C 0.6359(6) 0.0497(5) 0.64839(19) 0.0198(12) Uani 1 1 d . . . H30 H 0.5873 0.0881 0.6676 0.024 Uiso 1 1 calc R . . C19 C 0.9485(8) 0.4718(6) 0.7471(2) 0.0348(18) Uani 1 1 d . . . H31A H 1.0187 0.4258 0.7525 0.052 Uiso 1 1 calc R . . H31B H 0.9400 0.5270 0.7694 0.052 Uiso 1 1 calc R . . H31C H 0.9596 0.5119 0.7209 0.052 Uiso 1 1 calc R . . C20 C 0.7217(8) 0.4639(6) 0.7367(2) 0.0324(17) Uani 1 1 d . . . H32A H 0.7302 0.5020 0.7100 0.049 Uiso 1 1 calc R . . H32B H 0.7145 0.5208 0.7584 0.049 Uiso 1 1 calc R . . H32C H 0.6493 0.4139 0.7364 0.049 Uiso 1 1 calc R . . C31 C 0.9778(7) -0.3481(5) 0.5252(2) 0.0267(15) Uani 1 1 d . . . H33A H 1.0280 -0.3052 0.5450 0.040 Uiso 1 1 calc R . . H33B H 1.0296 -0.3827 0.5046 0.040 Uiso 1 1 calc R . . H33C H 0.9310 -0.4077 0.5396 0.040 Uiso 1 1 calc R . . C30 C 0.8035(7) -0.3341(6) 0.4731(2) 0.0307(16) Uani 1 1 d . . . H34A H 0.7557 -0.3910 0.4885 0.046 Uiso 1 1 calc R . . H34B H 0.8514 -0.3719 0.4522 0.046 Uiso 1 1 calc R . . H34C H 0.7495 -0.2814 0.4597 0.046 Uiso 1 1 calc R . . C51 C 0.2783(8) 0.0361(6) 0.2365(2) 0.0344(17) Uani 1 1 d . . . H35A H 0.2722 0.0026 0.2089 0.052 Uiso 1 1 calc R . . H35B H 0.2832 -0.0243 0.2570 0.052 Uiso 1 1 calc R . . H35C H 0.3510 0.0856 0.2382 0.052 Uiso 1 1 calc R . . C50 C 0.1667(7) 0.1058(5) 0.24490(18) 0.0259(15) Uani 1 1 d . . . C52 C 0.2276(7) 0.2623(5) 0.19671(18) 0.0217(13) Uani 1 1 d . . . N1 N 0.1831(5) 0.3219(4) 0.16344(16) 0.0224(12) Uani 1 1 d . . . H38 H 0.1110 0.3008 0.1545 0.027 Uiso 1 1 calc R . . C53 C 0.2431(6) 0.4147(5) 0.14202(18) 0.0197(13) Uani 1 1 d . . . C58 C 0.1717(6) 0.4741(5) 0.11292(17) 0.0181(12) Uani 1 1 d . . . H40 H 0.0898 0.4509 0.1088 0.022 Uiso 1 1 calc R . . C57 C 0.2213(6) 0.5671(5) 0.09011(17) 0.0183(12) Uani 1 1 d . . . C59 C 0.1382(6) 0.6262(5) 0.05998(17) 0.0181(12) Uani 1 1 d . . . C60 C 0.1097(7) 0.7666(5) 0.00359(18) 0.0219(14) Uani 1 1 d . . . C63 C 0.0373(7) 0.6748(5) -0.02245(17) 0.0204(13) Uani 1 1 d . . . C62 C 0.1958(8) 0.8347(6) -0.0268(2) 0.0320(17) Uani 1 1 d . . . H45A H 0.2458 0.8897 -0.0111 0.048 Uiso 1 1 calc R . . H45B H 0.1473 0.8748 -0.0470 0.048 Uiso 1 1 calc R . . H45C H 0.2478 0.7820 -0.0411 0.048 Uiso 1 1 calc R . . C61 C 0.0217(7) 0.8483(6) 0.0252(2) 0.0276(15) Uani 1 1 d . . . H46A H -0.0259 0.8063 0.0459 0.041 Uiso 1 1 calc R . . H46B H -0.0326 0.8799 0.0046 0.041 Uiso 1 1 calc R . . H46C H 0.0683 0.9101 0.0385 0.041 Uiso 1 1 calc R . . C56 C 0.3429(6) 0.6028(5) 0.09657(19) 0.0204(13) Uani 1 1 d . . . H47 H 0.3767 0.6654 0.0817 0.024 Uiso 1 1 calc R . . C55 C 0.4143(6) 0.5444(6) 0.12556(19) 0.0238(13) Uani 1 1 d . . . H48 H 0.4960 0.5682 0.1298 0.029 Uiso 1 1 calc R . . C54 C 0.3646(6) 0.4499(5) 0.14848(19) 0.0217(13) Uani 1 1 d . . . H49 H 0.4129 0.4115 0.1678 0.026 Uiso 1 1 calc R . . C48 C 0.1793(8) 0.1803(6) 0.2847(2) 0.0336(17) Uani 1 1 d . . . H50A H 0.2558 0.2244 0.2839 0.050 Uiso 1 1 calc R . . H50B H 0.1779 0.1311 0.3090 0.050 Uiso 1 1 calc R . . H50C H 0.1121 0.2319 0.2862 0.050 Uiso 1 1 calc R . . C49 C 0.0499(8) 0.0280(6) 0.2470(2) 0.0347(18) Uani 1 1 d . . . H51A H -0.0205 0.0749 0.2507 0.052 Uiso 1 1 calc R . . H51B H 0.0558 -0.0245 0.2702 0.052 Uiso 1 1 calc R . . H51C H 0.0411 -0.0153 0.2213 0.052 Uiso 1 1 calc R . . C43 C -0.3997(10) 0.6786(10) 0.3093(4) 0.068(3) Uani 1 1 d . . . H52A H -0.3763 0.6318 0.2859 0.102 Uiso 1 1 calc R . . H52B H -0.4532 0.7375 0.2997 0.102 Uiso 1 1 calc R . . H52C H -0.4420 0.6308 0.3297 0.102 Uiso 1 1 calc R . . C45 C -0.2824(8) 0.7362(7) 0.3296(3) 0.0406(19) Uani 1 1 d . . . C47 C -0.1012(6) 0.6490(6) 0.35977(19) 0.0221(13) Uani 1 1 d . . . N3 N -0.0553(6) 0.5425(5) 0.36477(17) 0.0251(12) Uani 1 1 d . . . H55 H -0.1053 0.4845 0.3602 0.030 Uiso 1 1 calc R . . C41 C 0.0650(6) 0.5166(5) 0.37656(17) 0.0209(13) Uani 1 1 d . . . C42 C 0.1417(6) 0.5886(5) 0.40164(17) 0.0195(12) Uani 1 1 d . . . H57 H 0.1138 0.6585 0.4117 0.023 Uiso 1 1 calc R . . C37 C 0.2602(7) 0.5541(5) 0.41129(18) 0.0220(13) Uani 1 1 d . . . C36 C 0.3478(6) 0.6213(5) 0.43958(19) 0.0204(12) Uani 1 1 d . . . C72 C 0.3827(7) 0.7619(6) 0.4954(2) 0.0311(16) Uani 1 1 d . . . C34 C 0.4596(7) 0.6734(6) 0.5192(2) 0.0298(16) Uani 1 1 d . . . C33 C 0.3014(9) 0.8164(8) 0.5289(3) 0.044(2) Uani 1 1 d . . . H62A H 0.2530 0.8749 0.5162 0.066 Uiso 1 1 calc R . . H62B H 0.3525 0.8507 0.5505 0.066 Uiso 1 1 calc R . . H62C H 0.2478 0.7577 0.5410 0.066 Uiso 1 1 calc R . . C35 C 0.4684(9) 0.8487(7) 0.4728(2) 0.043(2) Uani 1 1 d . . . H63A H 0.5124 0.8098 0.4512 0.065 Uiso 1 1 calc R . . H63B H 0.5260 0.8825 0.4926 0.065 Uiso 1 1 calc R . . H63C H 0.4208 0.9084 0.4606 0.065 Uiso 1 1 calc R . . C40 C 0.1065(7) 0.4099(5) 0.36257(18) 0.0223(14) Uani 1 1 d . . . H64 H 0.0547 0.3606 0.3470 0.027 Uiso 1 1 calc R . . C39 C 0.2244(8) 0.3784(6) 0.37209(19) 0.0286(15) Uani 1 1 d . . . H65 H 0.2525 0.3085 0.3620 0.034 Uiso 1 1 calc R . . C38 C 0.3013(7) 0.4484(6) 0.39621(19) 0.0259(14) Uani 1 1 d . . . H66 H 0.3805 0.4256 0.4025 0.031 Uiso 1 1 calc R . . C44 C -0.2119(9) 0.8096(8) 0.2977(3) 0.047(2) Uani 1 1 d . . . H67A H -0.1413 0.8461 0.3109 0.070 Uiso 1 1 calc R . . H67B H -0.2643 0.8677 0.2868 0.070 Uiso 1 1 calc R . . H67C H -0.1855 0.7613 0.2751 0.070 Uiso 1 1 calc R . . C46 C -0.3189(9) 0.8049(9) 0.3685(3) 0.054(2) Uani 1 1 d . . . H68A H -0.3635 0.7548 0.3875 0.081 Uiso 1 1 calc R . . H68B H -0.3700 0.8671 0.3602 0.081 Uiso 1 1 calc R . . H68C H -0.2461 0.8360 0.3821 0.081 Uiso 1 1 calc R . . C68 C 0.8553(11) 0.6248(8) 0.1469(3) 0.059(3) Uani 1 1 d . . . H69A H 0.8904 0.6275 0.1192 0.089 Uiso 1 1 calc R . . H69B H 0.7995 0.5590 0.1491 0.089 Uiso 1 1 calc R . . H69C H 0.9199 0.6186 0.1673 0.089 Uiso 1 1 calc R . . C69 C 0.7873(9) 0.7329(8) 0.1547(3) 0.048(2) Uani 1 1 d . . . C70 C 0.5944(12) 0.8250(11) 0.1497(4) 0.077(3) Uani 1 1 d . . . H71A H 0.6438 0.8950 0.1446 0.092 Uiso 1 1 calc R . . H71B H 0.5273 0.8222 0.1295 0.092 Uiso 1 1 calc R . . C71 C 0.5449(12) 0.8276(11) 0.1919(4) 0.076(3) Uani 1 1 d . . . H72A H 0.5041 0.7547 0.1981 0.114 Uiso 1 1 calc R . . H72B H 0.4870 0.8883 0.1940 0.114 Uiso 1 1 calc R . . H72C H 0.6107 0.8418 0.2116 0.114 Uiso 1 1 calc R . . C64 C 0.5466(13) 0.3264(11) 0.3082(4) 0.077(3) Uani 1 1 d . . . H73A H 0.6118 0.3137 0.2886 0.116 Uiso 1 1 calc R . . H73B H 0.5108 0.3995 0.3025 0.116 Uiso 1 1 calc R . . H73C H 0.4847 0.2655 0.3055 0.116 Uiso 1 1 calc R . . C65 C 0.5956(13) 0.3270(12) 0.3504(4) 0.080(4) Uani 1 1 d . . . H74A H 0.5288 0.3262 0.3706 0.097 Uiso 1 1 calc R . . H74B H 0.6465 0.3965 0.3550 0.097 Uiso 1 1 calc R . . C66 C 0.7885(9) 0.2335(8) 0.3455(3) 0.047(2) Uani 1 1 d . . . C67 C 0.8557(11) 0.1225(8) 0.3529(3) 0.058(3) Uani 1 1 d . . . H76A H 0.9173 0.1142 0.3316 0.087 Uiso 1 1 calc R . . H76B H 0.7980 0.0578 0.3517 0.087 Uiso 1 1 calc R . . H76C H 0.8944 0.1254 0.3800 0.087 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 O5 0.040(4) 0.024(2) 0.040(3) 0.0014(19) 0.019(2) -0.007(2) O4 0.035(3) 0.032(3) 0.042(3) 0.000(2) 0.006(2) -0.005(2) O2 0.018(3) 0.023(2) 0.035(2) 0.0057(17) 0.0026(19) 0.0019(19) O3 0.021(3) 0.037(3) 0.045(3) 0.011(2) 0.003(2) 0.008(2) O6 0.030(3) 0.019(2) 0.022(2) -0.0029(16) 0.0008(18) -0.0022(19) O10 0.014(2) 0.018(2) 0.032(2) 0.0040(16) 0.0028(17) 0.0009(17) O9 0.017(3) 0.022(2) 0.031(2) -0.0003(17) 0.0053(18) 0.0010(18) O8 0.014(2) 0.017(2) 0.029(2) 0.0007(15) 0.0008(17) 0.0033(17) O7 0.023(3) 0.021(2) 0.028(2) -0.0022(16) 0.0049(18) 0.0013(19) O19 0.018(3) 0.020(2) 0.028(2) -0.0004(16) -0.0012(17) 0.0014(18) O20 0.018(3) 0.020(2) 0.031(2) 0.0052(16) -0.0032(18) 0.0009(18) O18 0.015(3) 0.017(2) 0.028(2) 0.0040(15) 0.0012(17) 0.0018(17) O17 0.024(3) 0.023(2) 0.028(2) 0.0052(17) -0.0024(19) 0.0021(19) O14 0.037(3) 0.024(2) 0.042(3) 0.0038(19) -0.017(2) -0.008(2) O15 0.035(4) 0.034(3) 0.043(3) 0.006(2) -0.007(2) -0.006(2) O13 0.025(3) 0.031(3) 0.045(3) -0.004(2) -0.001(2) 0.009(2) O12 0.013(3) 0.025(2) 0.035(2) -0.0010(17) -0.0011(18) 0.0025(19) O22 0.042(4) 0.049(4) 0.073(4) -0.009(3) -0.012(3) -0.005(3) O21 0.070(6) 0.056(4) 0.079(5) 0.008(3) -0.003(4) -0.043(4) O23 0.036(4) 0.044(3) 0.079(4) 0.011(3) 0.008(3) -0.005(3) O24 0.057(5) 0.056(4) 0.083(5) 0.000(3) -0.002(4) -0.038(4) O1 0.019(3) 0.028(3) 0.062(3) 0.003(2) 0.016(2) -0.004(2) N8 0.017(3) 0.031(3) 0.035(3) 0.016(2) 0.009(2) 0.009(2) N6 0.014(3) 0.021(3) 0.025(2) -0.0027(19) 0.004(2) -0.005(2) O16 0.032(3) 0.016(2) 0.024(2) 0.0079(16) -0.0010(18) -0.0003(19) N2 0.020(3) 0.019(3) 0.024(2) 0.0059(19) -0.003(2) -0.005(2) O11 0.015(3) 0.032(3) 0.066(3) -0.001(2) -0.016(2) -0.003(2) N4 0.023(3) 0.029(3) 0.032(3) -0.012(2) -0.007(2) 0.011(2) C12 0.054(6) 0.052(5) 0.048(5) -0.004(4) 0.014(4) 0.017(5) C14 0.031(5) 0.046(5) 0.051(5) 0.007(4) 0.016(4) 0.010(4) C16 0.010(3) 0.025(3) 0.028(3) 0.004(2) 0.001(2) -0.002(2) N7 0.021(3) 0.020(3) 0.032(3) 0.004(2) 0.005(2) -0.003(2) C10 0.022(4) 0.020(3) 0.020(3) 0.001(2) 0.001(2) -0.003(3) C11 0.018(3) 0.016(3) 0.021(3) 0.002(2) 0.000(2) 0.002(2) C6 0.027(4) 0.016(3) 0.020(3) 0.002(2) 0.003(2) 0.004(3) C5 0.019(4) 0.026(3) 0.023(3) 0.001(2) 0.003(2) 0.004(3) C4 0.028(4) 0.033(4) 0.034(4) 0.014(3) 0.009(3) -0.001(3) C2 0.026(4) 0.031(4) 0.028(3) 0.004(3) 0.005(3) -0.010(3) C9 0.033(4) 0.018(3) 0.022(3) 0.003(2) 0.006(3) -0.001(3) C8 0.047(5) 0.016(3) 0.026(3) 0.004(2) 0.006(3) 0.010(3) C7 0.028(4) 0.026(3) 0.027(3) 0.004(2) 0.008(3) 0.009(3) C13 0.022(5) 0.067(7) 0.101(8) 0.015(6) 0.024(5) 0.007(5) C15 0.035(6) 0.068(6) 0.061(5) 0.009(4) 0.005(4) 0.026(5) C1 0.036(5) 0.052(5) 0.054(5) 0.028(4) 0.018(4) 0.019(4) C3 0.050(6) 0.028(4) 0.048(4) -0.002(3) 0.018(4) 0.001(4) C18 0.053(5) 0.026(3) 0.024(3) 0.002(2) 0.003(3) -0.003(3) C17 0.042(5) 0.019(3) 0.017(3) -0.002(2) 0.001(3) 0.003(3) C21 0.026(4) 0.020(3) 0.019(3) 0.003(2) -0.002(2) 0.000(3) N5 0.018(3) 0.023(3) 0.027(3) -0.002(2) 0.006(2) -0.006(2) C22 0.022(4) 0.014(3) 0.019(3) 0.003(2) 0.000(2) 0.001(2) C25 0.014(3) 0.017(3) 0.023(3) 0.003(2) -0.001(2) -0.004(2) C26 0.021(4) 0.015(3) 0.022(3) 0.003(2) 0.002(2) 0.002(2) C28 0.020(4) 0.012(3) 0.024(3) 0.005(2) 0.004(2) -0.002(2) C29 0.024(4) 0.016(3) 0.027(3) -0.003(2) 0.006(3) -0.003(3) C32 0.030(4) 0.016(3) 0.017(3) -0.003(2) -0.001(2) -0.003(3) C27 0.015(3) 0.018(3) 0.028(3) -0.001(2) -0.003(2) -0.003(2) C24 0.021(4) 0.024(3) 0.032(3) -0.002(2) 0.001(3) 0.000(3) C23 0.010(3) 0.021(3) 0.028(3) -0.001(2) 0.003(2) 0.002(2) C19 0.051(5) 0.028(4) 0.025(3) -0.007(3) -0.002(3) -0.005(3) C20 0.042(5) 0.020(3) 0.035(4) -0.002(3) 0.004(3) 0.002(3) C31 0.033(4) 0.018(3) 0.030(3) 0.000(2) 0.007(3) 0.003(3) C30 0.036(5) 0.024(3) 0.032(3) -0.008(3) 0.005(3) -0.012(3) C51 0.046(5) 0.020(3) 0.038(4) 0.006(3) -0.004(3) 0.005(3) C50 0.044(5) 0.016(3) 0.018(3) 0.006(2) 0.001(3) 0.002(3) C52 0.029(4) 0.016(3) 0.020(3) 0.001(2) 0.003(3) 0.004(3) N1 0.018(3) 0.022(3) 0.027(3) 0.007(2) -0.002(2) -0.002(2) C53 0.022(4) 0.015(3) 0.022(3) 0.001(2) 0.004(2) 0.002(2) C58 0.018(3) 0.014(3) 0.023(3) 0.003(2) 0.002(2) 0.001(2) C57 0.020(4) 0.016(3) 0.019(3) 0.000(2) 0.000(2) 0.002(2) C59 0.022(4) 0.011(3) 0.021(3) 0.001(2) 0.000(2) 0.000(2) C60 0.027(4) 0.013(3) 0.025(3) 0.006(2) -0.004(2) -0.006(3) C63 0.027(4) 0.015(3) 0.018(3) 0.006(2) 0.001(2) -0.001(3) C62 0.039(5) 0.026(3) 0.030(3) 0.014(3) -0.006(3) -0.013(3) C61 0.032(4) 0.021(3) 0.031(3) 0.003(2) -0.007(3) 0.007(3) C56 0.013(3) 0.016(3) 0.032(3) 0.005(2) 0.004(2) 0.001(2) C55 0.012(3) 0.028(3) 0.031(3) 0.006(2) 0.001(2) 0.004(3) C54 0.016(4) 0.021(3) 0.028(3) 0.004(2) 0.000(2) 0.005(2) C48 0.050(5) 0.025(3) 0.025(3) 0.002(2) 0.002(3) -0.005(3) C49 0.053(5) 0.026(4) 0.025(3) 0.009(3) 0.000(3) -0.005(3) C43 0.027(6) 0.075(7) 0.102(8) -0.010(6) -0.029(5) 0.007(5) C45 0.026(5) 0.042(4) 0.054(5) -0.002(3) -0.014(3) 0.007(4) C47 0.013(3) 0.024(3) 0.029(3) 0.001(2) 0.002(2) 0.000(3) N3 0.020(3) 0.022(3) 0.033(3) 0.000(2) -0.002(2) -0.002(2) C41 0.026(4) 0.019(3) 0.018(3) 0.002(2) 0.002(2) 0.001(3) C42 0.022(4) 0.017(3) 0.020(3) 0.000(2) 0.003(2) 0.006(2) C37 0.027(4) 0.019(3) 0.021(3) 0.003(2) 0.001(2) 0.008(3) C36 0.013(3) 0.021(3) 0.028(3) 0.003(2) -0.001(2) 0.007(2) C72 0.027(4) 0.032(4) 0.035(4) -0.011(3) -0.005(3) 0.004(3) C34 0.030(4) 0.034(4) 0.024(3) 0.001(3) -0.003(3) -0.011(3) C33 0.039(5) 0.044(5) 0.050(5) -0.019(4) -0.012(4) 0.018(4) C35 0.057(6) 0.027(4) 0.045(4) 0.009(3) -0.020(4) -0.008(4) C40 0.029(4) 0.014(3) 0.024(3) 0.000(2) -0.003(3) 0.000(3) C39 0.043(5) 0.020(3) 0.024(3) -0.002(2) -0.002(3) 0.011(3) C38 0.026(4) 0.026(3) 0.026(3) 0.000(2) -0.006(3) 0.016(3) C44 0.042(6) 0.049(5) 0.049(5) 0.007(4) -0.012(4) 0.014(4) C46 0.035(6) 0.068(6) 0.060(5) -0.008(4) -0.002(4) 0.013(5) C68 0.072(8) 0.033(5) 0.073(6) 0.000(4) 0.019(5) -0.001(5) C69 0.044(6) 0.051(5) 0.048(5) 0.010(4) 0.004(4) -0.017(4) C70 0.057(8) 0.073(8) 0.101(9) 0.000(6) -0.019(7) 0.010(6) C71 0.061(9) 0.073(8) 0.094(9) -0.014(6) 0.005(6) 0.009(6) C64 0.073(9) 0.069(7) 0.091(8) 0.010(6) -0.010(7) 0.013(7) C65 0.058(8) 0.079(8) 0.106(10) 0.009(7) 0.017(7) 0.027(7) C66 0.047(6) 0.042(5) 0.049(5) 0.002(3) -0.008(4) -0.014(4) C67 0.057(7) 0.038(5) 0.077(6) 0.005(4) -0.019(5) 0.000(5) _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 O5 C2 1.174(9) . ? O4 C2 1.345(8) . ? O4 H4 0.8200 . ? O2 C16 1.233(7) . ? O3 C5 1.240(9) . ? O6 C21 1.348(8) . ? O6 C17 1.477(7) . ? O10 C32 1.321(8) . ? O10 H6 0.8200 . ? O9 C32 1.209(8) . ? O8 C28 1.252(8) . ? O7 C21 1.209(8) . ? O19 C63 1.320(8) . ? O19 H19 0.8202 . ? O20 C63 1.221(8) . ? O18 C59 1.252(8) . ? O17 C52 1.196(9) . ? O14 C34 1.178(9) . ? O15 C34 1.340(8) . ? O15 H15 0.8202 . ? O13 C36 1.243(8) . ? O12 C47 1.230(8) . ? O22 C69 1.306(12) . ? O22 C70 1.487(14) . ? O21 C69 1.231(11) . ? O23 C66 1.326(12) . ? O23 C65 1.493(14) . ? O24 C66 1.208(10) . ? O1 C16 1.335(8) . ? O1 C14 1.476(10) . ? N8 C5 1.335(8) . ? N8 C4 1.466(8) . ? N8 H2 0.8600 . ? N6 C28 1.341(8) . ? N6 C29 1.474(8) . ? N6 H3 0.8600 . ? O16 C52 1.354(8) . ? O16 C50 1.485(7) . ? N2 C59 1.339(7) . ? N2 C60 1.466(8) . ? N2 H5 0.8600 . ? O11 C47 1.338(8) . ? O11 C45 1.467(10) . ? N4 C36 1.329(8) . ? N4 C72 1.473(8) . ? N4 H7 0.8600 . ? C12 C14 1.516(13) . ? C12 H1A 0.9600 . ? C12 H1B 0.9600 . ? C12 H1C 0.9600 . ? C14 C15 1.530(12) . ? C14 C13 1.540(12) . ? C16 N7 1.354(9) . ? N7 C10 1.392(9) . ? N7 H103 0.8600 . ? C10 C9 1.407(9) . ? C10 C11 1.409(8) . ? C11 C6 1.393(10) . ? C11 H6A 0.9300 . ? C6 C7 1.389(9) . ? C6 C5 1.504(8) . ? C4 C3 1.531(11) . ? C4 C1 1.537(11) . ? C4 C2 1.545(11) . ? C9 C8 1.378(11) . ? C9 H11 0.9300 . ? C8 C7 1.380(9) . ? C8 H12 0.9300 . ? C7 H13 0.9300 . ? C13 H14A 0.9600 . ? C13 H14B 0.9600 . ? C13 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C1 H16A 0.9600 . ? C1 H16B 0.9600 . ? C1 H16C 0.9600 . ? C3 H17A 0.9600 . ? C3 H17B 0.9600 . ? C3 H17C 0.9600 . ? C18 C17 1.530(9) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C17 C20 1.501(11) . ? C17 C19 1.524(10) . ? C21 N5 1.360(8) . ? N5 C22 1.410(8) . ? N5 H21A 0.8600 . ? C22 C23 1.389(9) . ? C22 C25 1.396(9) . ? C25 C26 1.393(8) . ? C25 H23 0.9300 . ? C26 C27 1.394(9) . ? C26 C28 1.498(9) . ? C29 C31 1.527(10) . ? C29 C30 1.541(9) . ? C29 C32 1.544(8) . ? C27 C24 1.381(9) . ? C27 H28 0.9300 . ? C24 C23 1.394(9) . ? C24 H29 0.9300 . ? C23 H30 0.9300 . ? C19 H31A 0.9600 . ? C19 H31B 0.9600 . ? C19 H31C 0.9600 . ? C20 H32A 0.9600 . ? C20 H32B 0.9600 . ? C20 H32C 0.9600 . ? C31 H33A 0.9600 . ? C31 H33B 0.9600 . ? C31 H33C 0.9600 . ? C30 H34A 0.9600 . ? C30 H34B 0.9600 . ? C30 H34C 0.9600 . ? C51 C50 1.503(11) . ? C51 H35A 0.9600 . ? C51 H35B 0.9600 . ? C51 H35C 0.9600 . ? C50 C49 1.531(10) . ? C50 C48 1.536(9) . ? C52 N1 1.361(8) . ? N1 C53 1.413(7) . ? N1 H38 0.8600 . ? C53 C54 1.383(10) . ? C53 C58 1.402(9) . ? C58 C57 1.391(8) . ? C58 H40 0.9300 . ? C57 C56 1.386(9) . ? C57 C59 1.496(8) . ? C60 C61 1.530(10) . ? C60 C63 1.539(8) . ? C60 C62 1.543(8) . ? C62 H45A 0.9600 . ? C62 H45B 0.9600 . ? C62 H45C 0.9600 . ? C61 H46A 0.9600 . ? C61 H46B 0.9600 . ? C61 H46C 0.9600 . ? C56 C55 1.394(9) . ? C56 H47 0.9300 . ? C55 C54 1.406(9) . ? C55 H48 0.9300 . ? C54 H49 0.9300 . ? C48 H50A 0.9600 . ? C48 H50B 0.9600 . ? C48 H50C 0.9600 . ? C49 H51A 0.9600 . ? C49 H51B 0.9600 . ? C49 H51C 0.9600 . ? C43 C45 1.558(12) . ? C43 H52A 0.9600 . ? C43 H52B 0.9600 . ? C43 H52C 0.9600 . ? C45 C44 1.515(12) . ? C45 C46 1.529(12) . ? C47 N3 1.354(9) . ? N3 C41 1.401(9) . ? N3 H55 0.8600 . ? C41 C40 1.401(9) . ? C41 C42 1.405(9) . ? C42 C37 1.394(9) . ? C42 H57 0.9300 . ? C37 C38 1.400(9) . ? C37 C36 1.505(9) . ? C72 C35 1.526(11) . ? C72 C33 1.535(11) . ? C72 C34 1.541(11) . ? C33 H62A 0.9600 . ? C33 H62B 0.9600 . ? C33 H62C 0.9600 . ? C35 H63A 0.9600 . ? C35 H63B 0.9600 . ? C35 H63C 0.9600 . ? C40 C39 1.376(10) . ? C40 H64 0.9300 . ? C39 C38 1.376(10) . ? C39 H65 0.9300 . ? C38 H66 0.9300 . ? C44 H67A 0.9600 . ? C44 H67B 0.9600 . ? C44 H67C 0.9600 . ? C46 H68A 0.9600 . ? C46 H68B 0.9600 . ? C46 H68C 0.9600 . ? C68 C69 1.494(15) . ? C68 H69A 0.9600 . ? C68 H69B 0.9600 . ? C68 H69C 0.9600 . ? C70 C71 1.447(17) . ? C70 H71A 0.9700 . ? C70 H71B 0.9700 . ? C71 H72A 0.9600 . ? C71 H72B 0.9600 . ? C71 H72C 0.9600 . ? C64 C65 1.445(18) . ? C64 H73A 0.9600 . ? C64 H73B 0.9600 . ? C64 H73C 0.9600 . ? C65 H74A 0.9700 . ? C65 H74B 0.9700 . ? C66 C67 1.516(14) . ? C67 H76A 0.9600 . ? C67 H76B 0.9600 . ? C67 H76C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O4 H4 109.5 . . ? C21 O6 C17 119.1(5) . . ? C32 O10 H6 109.5 . . ? C63 O19 H19 109.5 . . ? C34 O15 H15 109.5 . . ? C69 O22 C70 117.4(8) . . ? C66 O23 C65 116.3(8) . . ? C16 O1 C14 120.8(6) . . ? C5 N8 C4 120.8(6) . . ? C5 N8 H2 119.6 . . ? C4 N8 H2 119.6 . . ? C28 N6 C29 121.0(5) . . ? C28 N6 H3 119.5 . . ? C29 N6 H3 119.5 . . ? C52 O16 C50 119.0(5) . . ? C59 N2 C60 121.4(6) . . ? C59 N2 H5 119.3 . . ? C60 N2 H5 119.3 . . ? C47 O11 C45 120.6(6) . . ? C36 N4 C72 120.0(6) . . ? C36 N4 H7 120.0 . . ? C72 N4 H7 120.0 . . ? C14 C12 H1A 109.5 . . ? C14 C12 H1B 109.5 . . ? H1A C12 H1B 109.5 . . ? C14 C12 H1C 109.5 . . ? H1A C12 H1C 109.5 . . ? H1B C12 H1C 109.5 . . ? O1 C14 C12 110.5(7) . . ? O1 C14 C15 108.9(7) . . ? C12 C14 C15 113.4(8) . . ? O1 C14 C13 101.8(7) . . ? C12 C14 C13 111.7(8) . . ? C15 C14 C13 109.9(8) . . ? O2 C16 O1 126.3(6) . . ? O2 C16 N7 125.3(6) . . ? O1 C16 N7 108.4(5) . . ? C16 N7 C10 127.8(5) . . ? C16 N7 H103 116.1 . . ? C10 N7 H103 116.1 . . ? N7 C10 C9 116.3(6) . . ? N7 C10 C11 124.5(6) . . ? C9 C10 C11 119.1(6) . . ? C6 C11 C10 119.5(6) . . ? C6 C11 H6A 120.3 . . ? C10 C11 H6A 120.3 . . ? C7 C6 C11 120.2(6) . . ? C7 C6 C5 116.4(6) . . ? C11 C6 C5 123.3(5) . . ? O3 C5 N8 120.3(6) . . ? O3 C5 C6 120.5(6) . . ? N8 C5 C6 119.1(6) . . ? N8 C4 C3 110.3(6) . . ? N8 C4 C1 108.3(6) . . ? C3 C4 C1 114.2(7) . . ? N8 C4 C2 109.4(6) . . ? C3 C4 C2 109.0(6) . . ? C1 C4 C2 105.4(6) . . ? O5 C2 O4 121.5(7) . . ? O5 C2 C4 123.1(6) . . ? O4 C2 C4 115.2(6) . . ? C8 C9 C10 120.4(6) . . ? C8 C9 H11 119.8 . . ? C10 C9 H11 119.8 . . ? C9 C8 C7 120.2(6) . . ? C9 C8 H12 119.9 . . ? C7 C8 H12 119.9 . . ? C8 C7 C6 120.5(7) . . ? C8 C7 H13 119.7 . . ? C6 C7 H13 119.7 . . ? C14 C13 H14A 109.5 . . ? C14 C13 H14B 109.5 . . ? H14A C13 H14B 109.5 . . ? C14 C13 H14C 109.5 . . ? H14A C13 H14C 109.5 . . ? H14B C13 H14C 109.5 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C4 C1 H16A 109.5 . . ? C4 C1 H16B 109.5 . . ? H16A C1 H16B 109.5 . . ? C4 C1 H16C 109.5 . . ? H16A C1 H16C 109.5 . . ? H16B C1 H16C 109.5 . . ? C4 C3 H17A 109.5 . . ? C4 C3 H17B 109.5 . . ? H17A C3 H17B 109.5 . . ? C4 C3 H17C 109.5 . . ? H17A C3 H17C 109.5 . . ? H17B C3 H17C 109.5 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O6 C17 C20 110.9(5) . . ? O6 C17 C19 102.7(5) . . ? C20 C17 C19 110.4(6) . . ? O6 C17 C18 109.3(5) . . ? C20 C17 C18 112.9(6) . . ? C19 C17 C18 110.2(6) . . ? O7 C21 O6 125.4(6) . . ? O7 C21 N5 126.1(6) . . ? O6 C21 N5 108.5(6) . . ? C21 N5 C22 126.9(6) . . ? C21 N5 H21A 116.5 . . ? C22 N5 H21A 116.5 . . ? C23 C22 C25 119.4(5) . . ? C23 C22 N5 124.0(6) . . ? C25 C22 N5 116.5(6) . . ? C26 C25 C22 121.2(6) . . ? C26 C25 H23 119.4 . . ? C22 C25 H23 119.4 . . ? C25 C26 C27 119.2(6) . . ? C25 C26 C28 117.5(6) . . ? C27 C26 C28 123.2(5) . . ? O8 C28 N6 120.9(6) . . ? O8 C28 C26 120.5(5) . . ? N6 C28 C26 118.5(6) . . ? N6 C29 C31 110.9(5) . . ? N6 C29 C30 107.9(6) . . ? C31 C29 C30 110.8(5) . . ? N6 C29 C32 109.0(5) . . ? C31 C29 C32 110.7(6) . . ? C30 C29 C32 107.5(5) . . ? O9 C32 O10 124.2(6) . . ? O9 C32 C29 122.9(6) . . ? O10 C32 C29 112.8(6) . . ? C24 C27 C26 119.3(6) . . ? C24 C27 H28 120.4 . . ? C26 C27 H28 120.4 . . ? C27 C24 C23 121.9(6) . . ? C27 C24 H29 119.1 . . ? C23 C24 H29 119.1 . . ? C22 C23 C24 119.0(6) . . ? C22 C23 H30 120.5 . . ? C24 C23 H30 120.5 . . ? C17 C19 H31A 109.5 . . ? C17 C19 H31B 109.5 . . ? H31A C19 H31B 109.5 . . ? C17 C19 H31C 109.5 . . ? H31A C19 H31C 109.5 . . ? H31B C19 H31C 109.5 . . ? C17 C20 H32A 109.5 . . ? C17 C20 H32B 109.5 . . ? H32A C20 H32B 109.5 . . ? C17 C20 H32C 109.5 . . ? H32A C20 H32C 109.5 . . ? H32B C20 H32C 109.5 . . ? C29 C31 H33A 109.5 . . ? C29 C31 H33B 109.5 . . ? H33A C31 H33B 109.5 . . ? C29 C31 H33C 109.5 . . ? H33A C31 H33C 109.5 . . ? H33B C31 H33C 109.5 . . ? C29 C30 H34A 109.5 . . ? C29 C30 H34B 109.5 . . ? H34A C30 H34B 109.5 . . ? C29 C30 H34C 109.5 . . ? H34A C30 H34C 109.5 . . ? H34B C30 H34C 109.5 . . ? C50 C51 H35A 109.5 . . ? C50 C51 H35B 109.5 . . ? H35A C51 H35B 109.5 . . ? C50 C51 H35C 109.5 . . ? H35A C51 H35C 109.5 . . ? H35B C51 H35C 109.5 . . ? O16 C50 C51 110.3(5) . . ? O16 C50 C49 102.3(5) . . ? C51 C50 C49 111.2(6) . . ? O16 C50 C48 109.2(5) . . ? C51 C50 C48 112.9(6) . . ? C49 C50 C48 110.4(6) . . ? O17 C52 O16 125.3(5) . . ? O17 C52 N1 126.3(6) . . ? O16 C52 N1 108.4(6) . . ? C52 N1 C53 126.7(6) . . ? C52 N1 H38 116.6 . . ? C53 N1 H38 116.6 . . ? C54 C53 C58 119.4(5) . . ? C54 C53 N1 124.3(6) . . ? C58 C53 N1 116.3(6) . . ? C57 C58 C53 121.2(6) . . ? C57 C58 H40 119.4 . . ? C53 C58 H40 119.4 . . ? C56 C57 C58 119.5(6) . . ? C56 C57 C59 122.8(5) . . ? C58 C57 C59 117.6(6) . . ? O18 C59 N2 120.7(6) . . ? O18 C59 C57 120.2(5) . . ? N2 C59 C57 119.1(6) . . ? N2 C60 C61 111.1(5) . . ? N2 C60 C63 109.0(5) . . ? C61 C60 C63 110.6(6) . . ? N2 C60 C62 108.2(6) . . ? C61 C60 C62 110.3(5) . . ? C63 C60 C62 107.5(5) . . ? O20 C63 O19 123.5(6) . . ? O20 C63 C60 123.1(6) . . ? O19 C63 C60 113.3(6) . . ? C60 C62 H45A 109.5 . . ? C60 C62 H45B 109.5 . . ? H45A C62 H45B 109.5 . . ? C60 C62 H45C 109.5 . . ? H45A C62 H45C 109.5 . . ? H45B C62 H45C 109.5 . . ? C60 C61 H46A 109.5 . . ? C60 C61 H46B 109.5 . . ? H46A C61 H46B 109.5 . . ? C60 C61 H46C 109.5 . . ? H46A C61 H46C 109.5 . . ? H46B C61 H46C 109.5 . . ? C57 C56 C55 119.6(6) . . ? C57 C56 H47 120.2 . . ? C55 C56 H47 120.2 . . ? C56 C55 C54 121.0(6) . . ? C56 C55 H48 119.5 . . ? C54 C55 H48 119.5 . . ? C53 C54 C55 119.3(6) . . ? C53 C54 H49 120.4 . . ? C55 C54 H49 120.4 . . ? C50 C48 H50A 109.5 . . ? C50 C48 H50B 109.5 . . ? H50A C48 H50B 109.5 . . ? C50 C48 H50C 109.5 . . ? H50A C48 H50C 109.5 . . ? H50B C48 H50C 109.5 . . ? C50 C49 H51A 109.5 . . ? C50 C49 H51B 109.5 . . ? H51A C49 H51B 109.5 . . ? C50 C49 H51C 109.5 . . ? H51A C49 H51C 109.5 . . ? H51B C49 H51C 109.5 . . ? C45 C43 H52A 109.5 . . ? C45 C43 H52B 109.5 . . ? H52A C43 H52B 109.5 . . ? C45 C43 H52C 109.5 . . ? H52A C43 H52C 109.5 . . ? H52B C43 H52C 109.5 . . ? O11 C45 C44 111.6(7) . . ? O11 C45 C46 109.7(7) . . ? C44 C45 C46 112.8(7) . . ? O11 C45 C43 102.1(7) . . ? C44 C45 C43 110.6(8) . . ? C46 C45 C43 109.5(8) . . ? O12 C47 O11 125.9(6) . . ? O12 C47 N3 126.4(6) . . ? O11 C47 N3 107.6(5) . . ? C47 N3 C41 126.9(6) . . ? C47 N3 H55 116.5 . . ? C41 N3 H55 116.5 . . ? C40 C41 N3 115.7(6) . . ? C40 C41 C42 120.0(6) . . ? N3 C41 C42 124.3(6) . . ? C37 C42 C41 119.3(6) . . ? C37 C42 H57 120.3 . . ? C41 C42 H57 120.3 . . ? C42 C37 C38 120.0(6) . . ? C42 C37 C36 123.8(5) . . ? C38 C37 C36 116.1(6) . . ? O13 C36 N4 121.4(6) . . ? O13 C36 C37 120.3(6) . . ? N4 C36 C37 118.2(6) . . ? N4 C72 C35 110.4(6) . . ? N4 C72 C33 108.2(6) . . ? C35 C72 C33 113.9(7) . . ? N4 C72 C34 109.3(6) . . ? C35 C72 C34 109.6(6) . . ? C33 C72 C34 105.3(6) . . ? O14 C34 O15 121.4(7) . . ? O14 C34 C72 123.0(6) . . ? O15 C34 C72 115.4(6) . . ? C72 C33 H62A 109.5 . . ? C72 C33 H62B 109.5 . . ? H62A C33 H62B 109.5 . . ? C72 C33 H62C 109.5 . . ? H62A C33 H62C 109.5 . . ? H62B C33 H62C 109.5 . . ? C72 C35 H63A 109.5 . . ? C72 C35 H63B 109.5 . . ? H63A C35 H63B 109.5 . . ? C72 C35 H63C 109.5 . . ? H63A C35 H63C 109.5 . . ? H63B C35 H63C 109.5 . . ? C39 C40 C41 119.6(6) . . ? C39 C40 H64 120.2 . . ? C41 C40 H64 120.2 . . ? C40 C39 C38 121.2(6) . . ? C40 C39 H65 119.4 . . ? C38 C39 H65 119.4 . . ? C39 C38 C37 119.9(7) . . ? C39 C38 H66 120.0 . . ? C37 C38 H66 120.0 . . ? C45 C44 H67A 109.5 . . ? C45 C44 H67B 109.5 . . ? H67A C44 H67B 109.5 . . ? C45 C44 H67C 109.5 . . ? H67A C44 H67C 109.5 . . ? H67B C44 H67C 109.5 . . ? C45 C46 H68A 109.5 . . ? C45 C46 H68B 109.5 . . ? H68A C46 H68B 109.5 . . ? C45 C46 H68C 109.5 . . ? H68A C46 H68C 109.5 . . ? H68B C46 H68C 109.5 . . ? C69 C68 H69A 109.5 . . ? C69 C68 H69B 109.5 . . ? H69A C68 H69B 109.5 . . ? C69 C68 H69C 109.5 . . ? H69A C68 H69C 109.5 . . ? H69B C68 H69C 109.5 . . ? O21 C69 O22 122.7(10) . . ? O21 C69 C68 125.0(10) . . ? O22 C69 C68 112.4(8) . . ? C71 C70 O22 110.6(10) . . ? C71 C70 H71A 109.5 . . ? O22 C70 H71A 109.5 . . ? C71 C70 H71B 109.6 . . ? O22 C70 H71B 109.5 . . ? H71A C70 H71B 108.1 . . ? C70 C71 H72A 109.5 . . ? C70 C71 H72B 109.5 . . ? H72A C71 H72B 109.5 . . ? C70 C71 H72C 109.5 . . ? H72A C71 H72C 109.5 . . ? H72B C71 H72C 109.5 . . ? C65 C64 H73A 109.5 . . ? C65 C64 H73B 109.5 . . ? H73A C64 H73B 109.5 . . ? C65 C64 H73C 109.5 . . ? H73A C64 H73C 109.5 . . ? H73B C64 H73C 109.5 . . ? C64 C65 O23 108.6(10) . . ? C64 C65 H74A 110.0 . . ? O23 C65 H74A 110.0 . . ? C64 C65 H74B 110.0 . . ? O23 C65 H74B 110.0 . . ? H74A C65 H74B 108.4 . . ? O24 C66 O23 121.3(10) . . ? O24 C66 C67 126.9(10) . . ? O23 C66 C67 111.7(8) . . ? C66 C67 H76A 109.5 . . ? C66 C67 H76B 109.5 . . ? H76A C67 H76B 109.5 . . ? C66 C67 H76C 109.5 . . ? H76A C67 H76C 109.5 . . ? H76B C67 H76C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.600 _refine_diff_density_min -0.470 _refine_diff_density_rms 0.106 _database_code_depnum_ccdc_archive 'CCDC 912837'