# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Das, Gopal' _publ_contact_author_email gdas@iitg.ernet.in _publ_section_title ; Anion specificity induced conformational changes in cresol-based tripodal podands controlled by weak interactions: Structural and Hirshfeld surface analysis ; loop_ _publ_author_name S.Dey A.Pramanik G.Das data_p-cresol _database_code_depnum_ccdc_archive 'CCDC 766465' #TrackingRef 'all cif.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H33 N O3' _chemical_formula_weight 419.54 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-y, -x, z+1/2' 'x, x-y, z+1/2' '-x+y, y, z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' '-y+2/3, -x+1/3, z+5/6' 'x+2/3, x-y+1/3, z+5/6' '-x+y+2/3, y+1/3, z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-y+1/3, -x+2/3, z+7/6' 'x+1/3, x-y+2/3, z+7/6' '-x+y+1/3, y+2/3, z+7/6' _cell_length_a 20.4711(17) _cell_length_b 20.4711(17) _cell_length_c 9.5827(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3477.8(7) _cell_formula_units_Z 6 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3599 _cell_measurement_theta_min 3.44 _cell_measurement_theta_max 22.95 _exptl_crystal_description rectangular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1356 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.977 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details 'SADAS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 13751 _diffrn_reflns_av_R_equivalents 0.1102 _diffrn_reflns_av_sigmaI/netI 0.0533 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 28.46 _reflns_number_total 1907 _reflns_number_gt 1278 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0650P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1907 _refine_ls_number_parameters 95 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1295 _refine_ls_wR_factor_gt 0.1220 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 O1 O 0.81246(9) 0.47132(10) 0.99428(14) 0.0605(5) Uani 1 1 d . . . N1 N 0.6667 0.3333 1.1319(3) 0.0454(7) Uani 1 3 d S . . C1 C 0.73390(12) 0.40118(13) 1.1851(2) 0.0540(5) Uani 1 1 d . . . H1A H 0.7412 0.3930 1.2821 0.065 Uiso 1 1 calc R . . H1B H 0.7248 0.4433 1.1814 0.065 Uiso 1 1 calc R . . C2 C 0.80520(13) 0.42194(12) 1.1057(2) 0.0529(5) Uani 1 1 d . . . H2A H 0.8484 0.4467 1.1675 0.063 Uiso 1 1 calc R . . H2B H 0.8032 0.3768 1.0688 0.063 Uiso 1 1 calc R . . C3 C 0.87851(12) 0.50431(12) 0.91963(19) 0.0472(5) Uani 1 1 d . . . C4 C 0.88608(13) 0.55714(14) 0.8211(2) 0.0587(6) Uani 1 1 d . . . H4 H 0.8472 0.5676 0.8082 0.070 Uiso 1 1 calc R . . C5 C 0.95060(13) 0.59416(13) 0.7423(2) 0.0572(6) Uani 1 1 d . . . H5 H 0.9550 0.6300 0.6777 0.069 Uiso 1 1 calc R . . C6 C 1.00942(12) 0.57935(12) 0.7570(2) 0.0516(5) Uani 1 1 d . . . C7 C 1.00058(13) 0.52627(13) 0.8545(2) 0.0532(5) Uani 1 1 d . . . H7 H 1.0390 0.5150 0.8658 0.064 Uiso 1 1 calc R . . C8 C 0.93655(12) 0.48899(12) 0.9366(2) 0.0510(6) Uani 1 1 d . . . H8 H 0.9327 0.4539 1.0027 0.061 Uiso 1 1 calc R . . C9 C 1.07987(15) 0.62217(15) 0.6709(3) 0.0715(7) Uani 1 1 d . . . H9A H 1.1218 0.6244 0.7200 0.107 Uiso 1 1 calc R . . H9B H 1.0892 0.6724 0.6546 0.107 Uiso 1 1 calc R . . H9C H 1.0735 0.5970 0.5832 0.107 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 0.0500(10) 0.0745(12) 0.0624(10) 0.0137(8) 0.0029(7) 0.0352(8) N1 0.0433(9) 0.0433(9) 0.0495(15) 0.000 0.000 0.0216(5) C1 0.0536(13) 0.0535(14) 0.0518(13) -0.0105(10) -0.0034(10) 0.0245(11) C2 0.0503(13) 0.0496(13) 0.0577(13) -0.0021(10) -0.0047(10) 0.0242(11) C3 0.0430(12) 0.0518(12) 0.0479(12) -0.0035(9) -0.0031(8) 0.0245(10) C4 0.0588(14) 0.0691(15) 0.0601(14) 0.0054(11) -0.0044(11) 0.0410(13) C5 0.0627(15) 0.0580(14) 0.0535(12) 0.0063(10) -0.0012(11) 0.0321(12) C6 0.0517(13) 0.0444(12) 0.0540(11) -0.0091(9) -0.0016(10) 0.0206(11) C7 0.0472(11) 0.0524(13) 0.0644(12) -0.0049(10) -0.0025(10) 0.0282(10) C8 0.0529(13) 0.0472(12) 0.0575(13) 0.0009(10) -0.0037(10) 0.0285(11) C9 0.0620(16) 0.0577(15) 0.0835(19) -0.0011(13) 0.0133(13) 0.0214(13) _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 1.372(3) . ? O1 C2 1.426(3) . ? N1 C1 1.473(2) 3_665 ? N1 C1 1.474(2) . ? N1 C1 1.474(2) 2_655 ? C1 C2 1.506(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C8 1.382(3) . ? C3 C4 1.385(3) . ? C4 C5 1.374(3) . ? C4 H4 0.9300 . ? C5 C6 1.388(3) . ? C5 H5 0.9300 . ? C6 C7 1.375(3) . ? C6 C9 1.505(3) . ? C7 C8 1.385(3) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 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 117.85(16) . . ? C1 N1 C1 108.70(14) 3_665 . ? C1 N1 C1 108.70(14) 3_665 2_655 ? C1 N1 C1 108.70(14) . 2_655 ? N1 C1 C2 114.08(18) . . ? N1 C1 H1A 108.7 . . ? C2 C1 H1A 108.7 . . ? N1 C1 H1B 108.7 . . ? C2 C1 H1B 108.7 . . ? H1A C1 H1B 107.6 . . ? O1 C2 C1 108.72(18) . . ? O1 C2 H2A 109.9 . . ? C1 C2 H2A 109.9 . . ? O1 C2 H2B 109.9 . . ? C1 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? O1 C3 C8 125.06(19) . . ? O1 C3 C4 115.95(18) . . ? C8 C3 C4 119.0(2) . . ? C5 C4 C3 120.4(2) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 121.6(2) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C7 C6 C5 117.1(2) . . ? C7 C6 C9 122.8(2) . . ? C5 C6 C9 120.0(2) . . ? C6 C7 C8 122.4(2) . . ? C6 C7 H7 118.8 . . ? C8 C7 H7 118.8 . . ? C3 C8 C7 119.5(2) . . ? C3 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 C1 C2 79.9(3) 3_665 . . . ? C1 N1 C1 C2 -162.0(2) 2_655 . . . ? C3 O1 C2 C1 172.11(18) . . . . ? N1 C1 C2 O1 89.7(2) . . . . ? C2 O1 C3 C8 5.4(3) . . . . ? C2 O1 C3 C4 -174.19(19) . . . . ? O1 C3 C4 C5 179.1(2) . . . . ? C8 C3 C4 C5 -0.5(3) . . . . ? C3 C4 C5 C6 0.9(4) . . . . ? C4 C5 C6 C7 -0.4(3) . . . . ? C4 C5 C6 C9 -178.8(2) . . . . ? C5 C6 C7 C8 -0.6(3) . . . . ? C9 C6 C7 C8 177.8(2) . . . . ? O1 C3 C8 C7 -180.0(2) . . . . ? C4 C3 C8 C7 -0.4(3) . . . . ? C6 C7 C8 C3 1.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.46 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.143 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.039 data_p-cresol_ClO4 _database_code_depnum_ccdc_archive 'CCDC 766466' #TrackingRef 'all cif.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H34 Cl N O7' _chemical_formula_weight 520.00 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M 'R3c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-y, -x, z+1/2' '-x+y, y, z+1/2' 'x, x-y, z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' '-y+2/3, -x+1/3, z+5/6' '-x+y+2/3, y+1/3, z+5/6' 'x+2/3, x-y+1/3, z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-y+1/3, -x+2/3, z+7/6' '-x+y+1/3, y+2/3, z+7/6' 'x+1/3, x-y+2/3, z+7/6' _cell_length_a 12.58630(10) _cell_length_b 12.58630(10) _cell_length_c 28.7108(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3938.87(8) _cell_formula_units_Z 6 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5985 _cell_measurement_theta_min 3.24 _cell_measurement_theta_max 24.94 _exptl_crystal_description rectangular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1656 _exptl_absorpt_coefficient_mu 0.191 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.934 _exptl_absorpt_correction_T_max 0.944 _exptl_absorpt_process_details 'SADAS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 17213 _diffrn_reflns_av_R_equivalents 0.0631 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2175 _reflns_number_gt 1675 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0525P)^2^+0.6495P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2175 _refine_ls_number_parameters 113 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0906 _refine_ls_wR_factor_gt 0.0848 _refine_ls_goodness_of_fit_ref 0.956 _refine_ls_restrained_S_all 0.956 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 Cl1 Cl 0.0000 1.0000 0.05700(3) 0.0636(2) Uani 1 3 d S . . N1 N 0.6667 0.3333 0.24288(7) 0.0450(5) Uani 1 3 d S . . C3 C 0.59726(13) 0.11489(13) 0.13770(5) 0.0456(3) Uani 1 1 d . . . C4 C 0.55406(14) 0.14689(14) 0.09902(5) 0.0500(4) Uani 1 1 d . . . H4 H 0.4993 0.1755 0.1026 0.060 Uiso 1 1 calc R . . C5 C 0.59215(16) 0.13634(15) 0.05534(6) 0.0544(4) Uani 1 1 d . . . H5 H 0.5640 0.1600 0.0296 0.065 Uiso 1 1 calc R . . C6 C 0.67155(17) 0.09128(15) 0.04866(7) 0.0566(4) Uani 1 1 d . . . C8 C 0.67227(17) 0.06494(16) 0.13218(6) 0.0569(4) Uani 1 1 d . . . H8 H 0.6976 0.0383 0.1579 0.068 Uiso 1 1 calc R . . C2 C 0.61495(19) 0.12452(16) 0.22184(5) 0.0601(4) Uani 1 1 d . . . H2A H 0.7016 0.1531 0.2176 0.072 Uiso 1 1 calc R . . H2B H 0.5739 0.0390 0.2312 0.072 Uiso 1 1 calc R . . C7 C 0.70916(17) 0.05517(16) 0.08754(6) 0.0628(4) Uani 1 1 d . . . H7 H 0.7611 0.0231 0.0838 0.075 Uiso 1 1 calc R . . C1 C 0.59645(17) 0.20090(16) 0.25750(5) 0.0568(4) Uani 1 1 d . . . H1A H 0.6253 0.1911 0.2876 0.068 Uiso 1 1 calc R . . H1B H 0.5099 0.1743 0.2601 0.068 Uiso 1 1 calc R . . C9 C 0.7175(2) 0.0859(2) 0.00045(8) 0.0833(6) Uani 1 1 d . . . H9A H 0.8007 0.1513 -0.0030 0.125 Uiso 1 1 calc R . . H9B H 0.6668 0.0945 -0.0225 0.125 Uiso 1 1 calc R . . H9C H 0.7140 0.0086 -0.0037 0.125 Uiso 1 1 calc R . . O1 O 0.56226(11) 0.13945(11) 0.18001(4) 0.0544(3) Uani 1 1 d . . . O2 O 0.08597(17) 0.96795(17) 0.03964(7) 0.1064(6) Uani 1 1 d . . . O3 O 0.0000 1.0000 0.10565(12) 0.1433(18) Uani 1 3 d S . . H1N H 0.6667 0.3333 0.2125(11) 0.048(8) Uiso 1 3 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0701(3) 0.0701(3) 0.0507(4) 0.000 0.000 0.03507(15) N1 0.0540(8) 0.0540(8) 0.0268(9) 0.000 0.000 0.0270(4) C3 0.0487(8) 0.0431(7) 0.0436(7) -0.0044(6) 0.0009(6) 0.0219(7) C4 0.0504(8) 0.0509(8) 0.0500(8) -0.0053(7) -0.0020(7) 0.0262(7) C5 0.0581(9) 0.0499(9) 0.0484(8) -0.0050(7) -0.0041(7) 0.0219(7) C6 0.0587(9) 0.0461(8) 0.0549(8) -0.0101(7) 0.0086(7) 0.0186(7) C8 0.0671(10) 0.0545(9) 0.0581(10) -0.0020(7) -0.0022(7) 0.0373(9) C2 0.0808(12) 0.0567(9) 0.0458(8) 0.0034(7) -0.0017(7) 0.0367(9) C7 0.0647(10) 0.0587(9) 0.0729(11) -0.0116(8) 0.0052(8) 0.0369(9) C1 0.0719(10) 0.0562(10) 0.0357(7) 0.0063(6) 0.0056(7) 0.0270(8) C9 0.0960(15) 0.0808(14) 0.0661(11) -0.0113(10) 0.0236(10) 0.0390(11) O1 0.0638(7) 0.0675(7) 0.0399(5) -0.0044(5) -0.0010(5) 0.0388(6) O2 0.0985(11) 0.1142(13) 0.1271(16) 0.0126(11) 0.0271(11) 0.0687(11) O3 0.187(3) 0.187(3) 0.0552(17) 0.000 0.000 0.0937(15) _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 Cl1 O3 1.397(3) . ? Cl1 O2 1.4207(17) 3_465 ? Cl1 O2 1.4207(17) . ? Cl1 O2 1.4207(16) 2_675 ? N1 C1 1.5042(18) 2_655 ? N1 C1 1.5042(18) . ? N1 C1 1.5042(18) 3_665 ? C3 O1 1.3788(18) . ? C3 C8 1.380(2) . ? C3 C4 1.382(2) . ? C4 C5 1.372(2) . ? C5 C6 1.387(2) . ? C6 C7 1.376(3) . ? C6 C9 1.514(3) . ? C8 C7 1.389(2) . ? C2 O1 1.429(2) . ? C2 C1 1.500(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 O3 Cl1 O2 110.54(9) . 3_465 ? O3 Cl1 O2 110.54(9) . . ? O2 Cl1 O2 108.38(10) 3_465 . ? O3 Cl1 O2 110.54(9) . 2_675 ? O2 Cl1 O2 108.38(10) 3_465 2_675 ? O2 Cl1 O2 108.38(10) . 2_675 ? C1 N1 C1 112.53(8) 2_655 . ? C1 N1 C1 112.53(8) 2_655 3_665 ? C1 N1 C1 112.53(8) . 3_665 ? O1 C3 C8 124.84(14) . . ? O1 C3 C4 115.23(13) . . ? C8 C3 C4 119.91(13) . . ? C5 C4 C3 119.92(14) . . ? C4 C5 C6 121.59(16) . . ? C7 C6 C5 117.40(15) . . ? C7 C6 C9 121.67(17) . . ? C5 C6 C9 120.90(19) . . ? C3 C8 C7 118.76(15) . . ? O1 C2 C1 104.98(14) . . ? C6 C7 C8 122.27(15) . . ? C2 C1 N1 109.04(13) . . ? C3 O1 C2 119.31(12) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.130 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.025 data_o-CresolClO4 _database_code_depnum_ccdc_archive 'CCDC 766467' #TrackingRef 'all cif.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H34 N O3, Cl O4' _chemical_formula_sum 'C27 H34 Cl N O7' _chemical_formula_weight 520.00 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' Cl Cl 0.1484 0.1585 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.5293(2) _cell_length_b 10.7210(1) _cell_length_c 13.2388(2) _cell_angle_alpha 98.5670(12) _cell_angle_beta 109.2240(10) _cell_angle_gamma 97.0280(11) _cell_volume 1371.66(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5805 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 23.96 _exptl_crystal_description rectangular _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.183 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.936 _exptl_absorpt_correction_T_max 0.950 _exptl_absorpt_process_details 'SADAS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 19400 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 28.30 _reflns_number_total 6551 _reflns_number_gt 6070 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1810P)^2^+0.2464P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6551 _refine_ls_number_parameters 333 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0914 _refine_ls_R_factor_gt 0.0795 _refine_ls_wR_factor_ref 0.2108 _refine_ls_wR_factor_gt 0.1937 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.008 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 Cl1 Cl 0.29265(8) 0.07700(7) 0.22351(6) 0.0682(3) Uani 1 1 d . . . N1 N 0.8041(3) 0.8868(2) 0.1640(2) 0.0676(7) Uani 1 1 d . . . C2 C 1.0183(3) 0.9604(3) 0.3249(3) 0.0713(8) Uani 1 1 d . . . H2A H 1.0679 0.9185 0.2839 0.086 Uiso 1 1 calc R . . H2B H 1.0793 1.0351 0.3763 0.086 Uiso 1 1 calc R . . C1 C 0.8960(4) 0.9986(3) 0.2498(3) 0.0738(8) Uani 1 1 d . . . H1A H 0.9258 1.0637 0.2146 0.089 Uiso 1 1 calc R . . H1B H 0.8450 1.0359 0.2918 0.089 Uiso 1 1 calc R . . C3 C 1.0631(3) 0.8319(3) 0.4620(2) 0.0670(8) Uani 1 1 d . . . C4 C 1.2026(4) 0.8737(4) 0.4942(3) 0.0836(10) Uani 1 1 d . . . H4 H 1.2376 0.9335 0.4614 0.100 Uiso 1 1 calc R . . C8 C 1.0081(4) 0.7428(3) 0.5094(3) 0.0774(9) Uani 1 1 d . . . C6 C 1.2394(6) 0.7388(6) 0.6249(4) 0.1181(18) Uani 1 1 d . . . H5 H 1.2984 0.7088 0.6815 0.142 Uiso 1 1 calc R . . C7 C 1.0984(5) 0.6948(4) 0.5903(3) 0.0984(13) Uani 1 1 d . . . H6 H 1.0647 0.6327 0.6217 0.118 Uiso 1 1 calc R . . C9 C 0.8573(5) 0.6954(4) 0.4718(4) 0.0998(12) Uani 1 1 d . . . H8A H 0.8122 0.7663 0.4820 0.150 Uiso 1 1 calc R . . H8B H 0.8389 0.6340 0.5135 0.150 Uiso 1 1 calc R . . H8C H 0.8240 0.6554 0.3958 0.150 Uiso 1 1 calc R . . C5 C 1.2905(5) 0.8242(5) 0.5770(3) 0.1063(15) Uani 1 1 d . . . H9 H 1.3846 0.8506 0.5990 0.128 Uiso 1 1 calc R . . C20 C 0.8110(4) 0.7167(3) 0.0177(3) 0.0781(9) Uani 1 1 d . . . H11A H 0.7125 0.6899 -0.0064 0.094 Uiso 1 1 calc R . . H11B H 0.8399 0.6984 -0.0445 0.094 Uiso 1 1 calc R . . C19 C 0.8530(4) 0.8575(4) 0.0701(3) 0.0823(10) Uani 1 1 d . . . H10A H 0.9519 0.8814 0.0960 0.099 Uiso 1 1 calc R . . H10B H 0.8149 0.9078 0.0161 0.099 Uiso 1 1 calc R . . C10 C 0.6566(4) 0.9033(4) 0.1261(4) 0.0934(12) Uani 1 1 d . . . H12A H 0.6516 0.9925 0.1233 0.112 Uiso 1 1 calc R . . H12B H 0.6079 0.8520 0.0534 0.112 Uiso 1 1 calc R . . C11 C 0.5920(4) 0.8618(4) 0.2039(4) 0.1000(13) Uani 1 1 d . . . H13A H 0.6421 0.9097 0.2776 0.120 Uiso 1 1 calc R . . H13B H 0.4979 0.8746 0.1827 0.120 Uiso 1 1 calc R . . C21 C 0.8778(3) 0.5240(3) 0.0766(2) 0.0678(7) Uani 1 1 d . . . C26 C 0.9608(3) 0.4742(3) 0.1595(2) 0.0715(8) Uani 1 1 d . . . C22 C 0.7987(4) 0.4475(4) -0.0251(3) 0.0803(9) Uani 1 1 d . . . H15 H 0.7444 0.4825 -0.0806 0.096 Uiso 1 1 calc R . . C23 C 0.8034(4) 0.3170(4) -0.0410(3) 0.0913(11) Uani 1 1 d . . . H16 H 0.7516 0.2643 -0.1083 0.110 Uiso 1 1 calc R . . C25 C 0.9626(4) 0.3450(4) 0.1411(3) 0.0850(10) Uani 1 1 d . . . H18 H 1.0176 0.3099 0.1961 0.102 Uiso 1 1 calc R . . C24 C 0.8820(5) 0.2652(4) 0.0397(4) 0.0965(12) Uani 1 1 d . . . H17 H 0.8826 0.1776 0.0281 0.116 Uiso 1 1 calc R . . C27 C 1.0482(5) 0.5620(4) 0.2669(3) 0.0945(11) Uani 1 1 d . . . H20A H 1.1027 0.6318 0.2536 0.142 Uiso 1 1 calc R . . H20B H 1.1071 0.5149 0.3122 0.142 Uiso 1 1 calc R . . H20C H 0.9904 0.5952 0.3032 0.142 Uiso 1 1 calc R . . C17 C 0.5319(3) 0.5290(3) 0.2348(3) 0.0746(8) Uani 1 1 d . . . C12 C 0.5351(3) 0.6611(4) 0.2545(3) 0.0810(9) Uani 1 1 d . . . C16 C 0.4701(4) 0.4565(5) 0.2877(4) 0.0973(12) Uani 1 1 d . . . H25 H 0.4637 0.3679 0.2729 0.117 Uiso 1 1 calc R . . C13 C 0.4813(5) 0.7168(5) 0.3281(4) 0.1129(15) Uani 1 1 d . . . H22 H 0.4849 0.8050 0.3422 0.135 Uiso 1 1 calc R . . C14 C 0.4209(6) 0.6371(7) 0.3811(5) 0.1304(19) Uani 1 1 d . . . H26 H 0.3829 0.6730 0.4302 0.156 Uiso 1 1 calc R . . C15 C 0.4171(5) 0.5100(7) 0.3623(5) 0.1252(17) Uani 1 1 d . . . H23 H 0.3788 0.4585 0.3994 0.150 Uiso 1 1 calc R . . C18 C 0.5922(4) 0.4703(4) 0.1562(3) 0.0898(10) Uani 1 1 d . . . H27A H 0.5427 0.4828 0.0844 0.135 Uiso 1 1 calc R . . H27B H 0.5862 0.3801 0.1556 0.135 Uiso 1 1 calc R . . H27C H 0.6864 0.5103 0.1780 0.135 Uiso 1 1 calc R . . O5 O 0.3840(3) 0.1108(4) 0.1713(3) 0.1187(11) Uani 1 1 d . . . O7 O 0.3174(6) -0.0219(6) 0.2720(6) 0.227(3) Uani 1 1 d . . . O4 O 0.3039(9) 0.1695(6) 0.3074(6) 0.278(4) Uani 1 1 d . . . O1 O 0.9683(2) 0.8746(2) 0.38099(16) 0.0698(6) Uani 1 1 d . . . O3 O 0.8788(2) 0.6537(2) 0.10176(16) 0.0757(6) Uani 1 1 d . . . O2 O 0.5981(3) 0.7305(2) 0.1971(2) 0.0880(7) Uani 1 1 d . . . O6 O 0.1590(4) 0.0634(7) 0.1574(4) 0.195(3) Uani 1 1 d . . . H1N H 0.811(3) 0.819(3) 0.192(2) 0.052(7) 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 Cl1 0.0652(5) 0.0677(5) 0.0677(5) 0.0159(3) 0.0171(3) 0.0121(3) N1 0.0708(16) 0.0639(13) 0.0680(14) 0.0293(12) 0.0163(12) 0.0155(12) C2 0.0694(19) 0.0780(18) 0.0646(16) 0.0164(14) 0.0219(14) 0.0093(15) C1 0.085(2) 0.0657(16) 0.0704(18) 0.0220(14) 0.0237(16) 0.0137(15) C3 0.0688(18) 0.0806(18) 0.0520(14) 0.0088(13) 0.0184(13) 0.0292(15) C4 0.071(2) 0.116(3) 0.0629(18) 0.0105(17) 0.0185(15) 0.0358(19) C8 0.096(2) 0.084(2) 0.0611(17) 0.0193(15) 0.0308(17) 0.0325(18) C6 0.134(4) 0.158(4) 0.077(2) 0.038(3) 0.027(3) 0.092(4) C7 0.131(4) 0.102(3) 0.078(2) 0.035(2) 0.038(2) 0.055(3) C9 0.109(3) 0.102(3) 0.102(3) 0.041(2) 0.046(3) 0.021(2) C5 0.083(3) 0.151(4) 0.079(2) 0.006(3) 0.015(2) 0.061(3) C20 0.085(2) 0.087(2) 0.0582(16) 0.0181(15) 0.0188(16) 0.0150(17) C19 0.096(3) 0.089(2) 0.0602(17) 0.0277(15) 0.0245(17) 0.0044(18) C10 0.076(2) 0.074(2) 0.117(3) 0.036(2) 0.007(2) 0.0210(17) C11 0.067(2) 0.081(2) 0.151(4) 0.020(2) 0.034(2) 0.0253(18) C21 0.0616(17) 0.0807(19) 0.0630(16) 0.0090(14) 0.0274(14) 0.0120(14) C26 0.0714(19) 0.087(2) 0.0607(16) 0.0133(14) 0.0298(15) 0.0171(16) C22 0.071(2) 0.093(2) 0.0665(18) 0.0027(16) 0.0198(15) 0.0091(17) C23 0.096(3) 0.092(2) 0.075(2) -0.0042(19) 0.031(2) -0.002(2) C25 0.098(3) 0.089(2) 0.078(2) 0.0218(18) 0.040(2) 0.029(2) C24 0.122(3) 0.079(2) 0.095(3) 0.010(2) 0.052(3) 0.017(2) C27 0.108(3) 0.099(2) 0.0681(19) 0.0188(18) 0.017(2) 0.026(2) C17 0.0529(16) 0.086(2) 0.084(2) 0.0273(17) 0.0175(15) 0.0184(14) C12 0.0522(16) 0.100(2) 0.094(2) 0.0194(19) 0.0273(16) 0.0201(16) C16 0.073(2) 0.117(3) 0.125(3) 0.058(3) 0.044(2) 0.035(2) C13 0.092(3) 0.111(3) 0.146(4) 0.008(3) 0.062(3) 0.024(2) C14 0.113(4) 0.170(5) 0.147(4) 0.041(4) 0.086(4) 0.046(4) C15 0.100(3) 0.151(5) 0.152(5) 0.063(4) 0.063(3) 0.032(3) C18 0.090(3) 0.092(2) 0.089(2) 0.0280(19) 0.027(2) 0.022(2) O5 0.094(2) 0.169(3) 0.111(2) 0.053(2) 0.0495(18) 0.022(2) O7 0.229(6) 0.279(6) 0.345(8) 0.244(7) 0.203(6) 0.177(5) O4 0.345(9) 0.209(6) 0.269(7) -0.106(5) 0.216(7) -0.109(6) O1 0.0658(12) 0.0835(13) 0.0624(11) 0.0259(10) 0.0204(10) 0.0160(10) O3 0.0827(15) 0.0842(14) 0.0567(11) 0.0129(10) 0.0178(10) 0.0228(12) O2 0.0793(15) 0.0752(14) 0.123(2) 0.0269(13) 0.0471(15) 0.0229(12) O6 0.086(2) 0.372(8) 0.147(3) 0.146(4) 0.032(2) 0.026(3) _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 Cl1 O7 1.329(4) . ? Cl1 O4 1.337(5) . ? Cl1 O6 1.367(4) . ? Cl1 O5 1.400(3) . ? N1 C1 1.500(4) . ? N1 C19 1.502(4) . ? N1 C10 1.508(5) . ? C2 O1 1.420(4) . ? C2 C1 1.491(5) . ? C3 O1 1.382(4) . ? C3 C4 1.382(5) . ? C3 C8 1.387(5) . ? C4 C5 1.402(5) . ? C8 C7 1.389(5) . ? C8 C9 1.494(6) . ? C6 C5 1.344(7) . ? C6 C7 1.398(7) . ? C20 O3 1.422(4) . ? C20 C19 1.510(5) . ? C10 C11 1.498(6) . ? C11 O2 1.408(4) . ? C21 O3 1.379(4) . ? C21 C26 1.382(5) . ? C21 C22 1.394(4) . ? C26 C25 1.373(5) . ? C26 C27 1.511(5) . ? C22 C23 1.392(5) . ? C23 C24 1.357(6) . ? C25 C24 1.408(6) . ? C17 C16 1.361(5) . ? C17 C12 1.396(5) . ? C17 C18 1.490(5) . ? C12 C13 1.379(6) . ? C12 O2 1.396(4) . ? C16 C15 1.374(7) . ? C13 C14 1.403(7) . ? C14 C15 1.342(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O7 Cl1 O4 101.8(5) . . ? O7 Cl1 O6 112.8(4) . . ? O4 Cl1 O6 102.9(5) . . ? O7 Cl1 O5 113.8(3) . . ? O4 Cl1 O5 112.0(3) . . ? O6 Cl1 O5 112.5(2) . . ? C1 N1 C19 112.1(3) . . ? C1 N1 C10 112.2(3) . . ? C19 N1 C10 111.9(3) . . ? O1 C2 C1 106.3(3) . . ? C2 C1 N1 112.0(3) . . ? O1 C3 C4 123.2(3) . . ? O1 C3 C8 115.0(3) . . ? C4 C3 C8 121.9(3) . . ? C3 C4 C5 118.8(4) . . ? C3 C8 C7 117.7(4) . . ? C3 C8 C9 121.5(3) . . ? C7 C8 C9 120.8(4) . . ? C5 C6 C7 120.5(4) . . ? C8 C7 C6 120.7(4) . . ? C6 C5 C4 120.4(5) . . ? O3 C20 C19 104.4(3) . . ? N1 C19 C20 110.9(3) . . ? C11 C10 N1 109.2(3) . . ? O2 C11 C10 105.0(3) . . ? O3 C21 C26 115.3(3) . . ? O3 C21 C22 122.7(3) . . ? C26 C21 C22 121.9(3) . . ? C25 C26 C21 118.5(3) . . ? C25 C26 C27 121.6(3) . . ? C21 C26 C27 119.9(3) . . ? C23 C22 C21 117.9(4) . . ? C24 C23 C22 121.4(3) . . ? C26 C25 C24 120.7(4) . . ? C23 C24 C25 119.5(4) . . ? C16 C17 C12 118.1(4) . . ? C16 C17 C18 121.7(4) . . ? C12 C17 C18 120.2(3) . . ? C13 C12 C17 120.7(4) . . ? C13 C12 O2 123.6(4) . . ? C17 C12 O2 115.7(3) . . ? C17 C16 C15 122.2(5) . . ? C12 C13 C14 118.4(5) . . ? C15 C14 C13 121.1(5) . . ? C14 C15 C16 119.4(5) . . ? C3 O1 C2 117.8(2) . . ? C21 O3 C20 119.3(2) . . ? C12 O2 C11 118.6(3) . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 1.180 _refine_diff_density_min -0.552 _refine_diff_density_rms 0.057 data_m-CresolClO4 _database_code_depnum_ccdc_archive 'CCDC 766468' #TrackingRef 'all cif.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H34 Cl N O7' _chemical_formula_weight 520.00 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' Cl Cl 0.1484 0.1585 '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 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.5714(2) _cell_length_b 14.9166(2) _cell_length_c 15.3649(3) _cell_angle_alpha 93.2570(11) _cell_angle_beta 96.0490(10) _cell_angle_gamma 116.2500(11) _cell_volume 2755.43(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9944 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description recetangular _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.181 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.938 _exptl_absorpt_correction_T_max 0.968 _exptl_absorpt_process_details 'SADAS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 onega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28724 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 28.24 _reflns_number_total 13120 _reflns_number_gt 12127 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1214P)^2^+0.3720P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11120 _refine_ls_number_parameters 664 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0938 _refine_ls_R_factor_gt 0.0654 _refine_ls_wR_factor_ref 0.2320 _refine_ls_wR_factor_gt 0.1990 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.008 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 Cl1 Cl 0.70353(6) 0.51759(6) 0.11224(5) 0.0713(3) Uani 1 1 d . . . Cl2 Cl 0.81358(8) 0.95228(7) 0.33107(6) 0.0908(3) Uani 1 1 d . . . N1 N 0.1636(2) 0.28276(19) 0.52850(16) 0.0644(7) Uani 1 1 d . . . N2 N 0.6977(2) 0.76243(18) 1.00086(16) 0.0643(7) Uani 1 1 d . . . O4 O 0.85169(17) 0.95940(13) 1.00183(12) 0.0698(5) Uani 1 1 d . . . O1 O 0.08586(17) 0.31383(16) 0.36630(13) 0.0738(6) Uani 1 1 d . . . O2 O 0.14919(18) 0.45519(15) 0.56810(13) 0.0779(6) Uani 1 1 d . . . O3 O 0.35008(16) 0.41196(15) 0.46757(13) 0.0704(5) Uani 1 1 d . . . O5 O 0.55860(18) 0.84630(15) 0.98951(15) 0.0805(6) Uani 1 1 d . . . O6 O 0.68564(18) 0.78687(17) 0.82278(14) 0.0792(6) Uani 1 1 d . . . O7 O 0.6823(2) 0.43893(17) 0.16473(16) 0.1001(8) Uani 1 1 d . . . O10 O 0.7344(3) 0.60924(19) 0.1672(2) 0.1262(10) Uani 1 1 d . . . O9 O 0.6080(2) 0.4980(2) 0.0548(2) 0.1460(14) Uani 1 1 d . . . O12 O 0.7504(5) 0.8662(3) 0.2818(2) 0.216(2) Uani 1 1 d . . . O14 O 0.8659(3) 1.03246(18) 0.28274(16) 0.1275(11) Uani 1 1 d . . . O11 O 0.8835(3) 0.9521(3) 0.4018(2) 0.1795(18) Uani 1 1 d . . . O13 O 0.7339(5) 0.9647(5) 0.3781(4) 0.253(3) Uani 1 1 d . . . O8 O 0.7906(4) 0.5334(4) 0.0676(3) 0.2005(19) Uani 1 1 d . . . C3 C 0.0540(3) 0.3660(2) 0.30708(19) 0.0654(8) Uani 1 1 d . . . C4 C 0.1362(3) 0.4307(2) 0.26379(19) 0.0692(8) Uani 1 1 d . . . H4 H 0.2081 0.4380 0.2762 0.083 Uiso 1 1 calc R . . C5 C 0.1126(3) 0.4853(2) 0.2017(2) 0.0792(9) Uani 1 1 d . . . C8 C -0.0540(3) 0.3539(3) 0.2913(2) 0.0766(9) Uani 1 1 d . . . H8 H -0.1093 0.3105 0.3209 0.092 Uiso 1 1 calc R . . C2 C 0.0068(3) 0.2459(2) 0.4144(2) 0.0735(8) Uani 1 1 d . . . H2A H -0.0551 0.1940 0.3747 0.088 Uiso 1 1 calc R . . H2B H -0.0213 0.2812 0.4518 0.088 Uiso 1 1 calc R . . C6 C 0.0042(3) 0.4729(3) 0.1852(2) 0.0830(10) Uani 1 1 d . . . H6 H -0.0138 0.5084 0.1438 0.100 Uiso 1 1 calc R . . C1 C 0.0674(3) 0.2012(2) 0.4687(2) 0.0750(9) Uani 1 1 d . . . H1A H 0.0940 0.1653 0.4305 0.090 Uiso 1 1 calc R . . H1B H 0.0175 0.1536 0.5035 0.090 Uiso 1 1 calc R . . C9 C 0.2037(4) 0.5554(3) 0.1530(3) 0.1167(14) Uani 1 1 d . . . H9A H 0.2706 0.5494 0.1695 0.175 Uiso 1 1 calc R . . H9B H 0.2172 0.6236 0.1681 0.175 Uiso 1 1 calc R . . H9C H 0.1808 0.5373 0.0906 0.175 Uiso 1 1 calc R . . C12 C 0.1983(2) 0.5568(2) 0.5621(2) 0.0648(7) Uani 1 1 d . . . C13 C 0.1608(3) 0.5848(2) 0.4857(2) 0.0685(8) Uani 1 1 d . . . H13 H 0.1065 0.5357 0.4436 0.082 Uiso 1 1 calc R . . C11 C 0.1908(3) 0.4180(2) 0.6399(2) 0.0787(9) Uani 1 1 d . . . H11A H 0.1712 0.4358 0.6950 0.094 Uiso 1 1 calc R . . H11B H 0.2709 0.4450 0.6455 0.094 Uiso 1 1 calc R . . C14 C 0.2033(3) 0.6846(3) 0.4717(2) 0.0789(9) Uani 1 1 d . . . C10 C 0.1353(3) 0.3062(2) 0.6159(2) 0.0796(9) Uani 1 1 d . . . H10A H 0.0555 0.2802 0.6125 0.096 Uiso 1 1 calc R . . H10B H 0.1604 0.2746 0.6606 0.096 Uiso 1 1 calc R . . C17 C 0.2793(3) 0.6281(2) 0.6258(2) 0.0732(8) Uani 1 1 d . . . H17 H 0.3061 0.6095 0.6763 0.088 Uiso 1 1 calc R . . C16 C 0.3184(3) 0.7273(3) 0.6117(3) 0.0966(11) Uani 1 1 d . . . H16 H 0.3711 0.7769 0.6543 0.116 Uiso 1 1 calc R . . C18 C 0.1657(4) 0.7130(3) 0.3863(3) 0.1088(13) Uani 1 1 d . . . H18A H 0.0970 0.6584 0.3584 0.163 Uiso 1 1 calc R . . H18B H 0.2211 0.7268 0.3481 0.163 Uiso 1 1 calc R . . H18C H 0.1552 0.7718 0.3981 0.163 Uiso 1 1 calc R . . C15 C 0.2818(3) 0.7551(3) 0.5363(3) 0.0968(12) Uani 1 1 d . . . H15 H 0.3107 0.8229 0.5286 0.116 Uiso 1 1 calc R . . C21 C 0.4000(2) 0.4689(3) 0.4037(2) 0.0696(8) Uani 1 1 d . . . C22 C 0.4074(2) 0.5641(3) 0.4094(2) 0.0745(9) Uani 1 1 d . . . H22 H 0.3782 0.5841 0.4545 0.089 Uiso 1 1 calc R . . C20 C 0.3276(3) 0.3088(2) 0.4616(2) 0.0794(9) Uani 1 1 d . . . H20A H 0.3961 0.3026 0.4668 0.095 Uiso 1 1 calc R . . H20B H 0.2826 0.2730 0.4058 0.095 Uiso 1 1 calc R . . C19 C 0.2661(3) 0.2688(2) 0.5366(2) 0.0779(9) Uani 1 1 d . . . H19A H 0.2465 0.1978 0.5363 0.093 Uiso 1 1 calc R . . H19B H 0.3129 0.3039 0.5919 0.093 Uiso 1 1 calc R . . C26 C 0.4415(3) 0.4351(3) 0.3372(2) 0.0963(12) Uani 1 1 d . . . H26 H 0.4367 0.3708 0.3333 0.116 Uiso 1 1 calc R . . C23 C 0.4567(3) 0.6305(3) 0.3504(3) 0.0976(13) Uani 1 1 d . . . C24 C 0.4981(3) 0.5956(5) 0.2832(3) 0.126(2) Uani 1 1 d . . . H24 H 0.5318 0.6380 0.2418 0.151 Uiso 1 1 calc R . . C25 C 0.4900(3) 0.5009(5) 0.2774(3) 0.1232(18) Uani 1 1 d . . . H25 H 0.5180 0.4802 0.2318 0.148 Uiso 1 1 calc R . . C27 C 0.4668(4) 0.7353(4) 0.3579(4) 0.146(2) Uani 1 1 d . . . H27A H 0.4046 0.7357 0.3222 0.218 Uiso 1 1 calc R . . H27B H 0.5343 0.7803 0.3380 0.218 Uiso 1 1 calc R . . H27C H 0.4681 0.7568 0.4183 0.218 Uiso 1 1 calc R . . C7 C -0.0759(3) 0.4092(3) 0.2294(2) 0.0854(10) Uani 1 1 d . . . H7 H -0.1475 0.4028 0.2176 0.102 Uiso 1 1 calc R . . C39 C 0.5078(3) 0.8845(2) 0.9302(2) 0.0724(8) Uani 1 1 d . . . C40 C 0.5733(3) 0.9820(3) 0.9149(2) 0.0789(9) Uani 1 1 d . . . H40 H 0.6464 1.0156 0.9429 0.095 Uiso 1 1 calc R . . C38 C 0.5089(3) 0.7407(2) 0.9937(3) 0.0831(10) Uani 1 1 d . . . H38A H 0.4887 0.7041 0.9352 0.100 Uiso 1 1 calc R . . H38B H 0.4431 0.7194 1.0224 0.100 Uiso 1 1 calc R . . C37 C 0.5974(3) 0.7242(2) 1.0470(2) 0.0791(9) Uani 1 1 d . . . H37A H 0.6157 0.7601 1.1056 0.095 Uiso 1 1 calc R . . H37B H 0.5714 0.6531 1.0523 0.095 Uiso 1 1 calc R . . C44 C 0.3995(3) 0.8327(3) 0.8903(3) 0.0971(11) Uani 1 1 d . . . H44 H 0.3547 0.7669 0.9003 0.116 Uiso 1 1 calc R . . C41 C 0.5328(4) 1.0300(3) 0.8593(3) 0.0976(12) Uani 1 1 d . . . C42 C 0.4239(5) 0.9783(5) 0.8194(3) 0.1179(16) Uani 1 1 d . . . H42 H 0.3943 1.0097 0.7816 0.142 Uiso 1 1 calc R . . C43 C 0.3598(4) 0.8833(4) 0.8342(3) 0.1167(15) Uani 1 1 d . . . H43 H 0.2868 0.8504 0.8062 0.140 Uiso 1 1 calc R . . C45 C 0.6055(5) 1.1360(4) 0.8424(4) 0.152(2) Uani 1 1 d . . . H45A H 0.5623 1.1724 0.8370 0.227 Uiso 1 1 calc R . . H45B H 0.6358 1.1349 0.7889 0.227 Uiso 1 1 calc R . . H45C H 0.6649 1.1686 0.8907 0.227 Uiso 1 1 calc R . . C31 C 0.8959(2) 1.0944(2) 0.91861(19) 0.0627(7) Uani 1 1 d . . . H31 H 0.8760 1.0479 0.8691 0.075 Uiso 1 1 calc R . . C29 C 0.8389(3) 0.9200(2) 1.08472(19) 0.0714(8) Uani 1 1 d . . . H29A H 0.7820 0.9297 1.1112 0.086 Uiso 1 1 calc R . . H29B H 0.9081 0.9526 1.1250 0.086 Uiso 1 1 calc R . . C30 C 0.8877(2) 1.0616(2) 1.00075(19) 0.0581(7) Uani 1 1 d . . . C32 C 0.9332(2) 1.1953(2) 0.9082(2) 0.0685(8) Uani 1 1 d . . . C28 C 0.8058(3) 0.8107(2) 1.0639(2) 0.0749(9) Uani 1 1 d . . . H28A H 0.7964 0.7785 1.1177 0.090 Uiso 1 1 calc R . . H28B H 0.8633 0.8021 1.0374 0.090 Uiso 1 1 calc R . . C35 C 0.9151(3) 1.1282(2) 1.0754(2) 0.0688(8) Uani 1 1 d . . . H35 H 0.9085 1.1062 1.1309 0.083 Uiso 1 1 calc R . . C33 C 0.9627(3) 1.2625(2) 0.9832(2) 0.0803(9) Uani 1 1 d . . . H33 H 0.9893 1.3309 0.9783 0.096 Uiso 1 1 calc R . . C34 C 0.9530(3) 1.2293(2) 1.0648(2) 0.0837(10) Uani 1 1 d . . . H34 H 0.9724 1.2758 1.1142 0.100 Uiso 1 1 calc R . . C36 C 0.9449(4) 1.2293(3) 0.8180(2) 0.1031(12) Uani 1 1 d . . . H36A H 0.8792 1.2343 0.7946 0.155 Uiso 1 1 calc R . . H36B H 0.9546 1.1815 0.7798 0.155 Uiso 1 1 calc R . . H36C H 1.0082 1.2939 0.8218 0.155 Uiso 1 1 calc R . . C48 C 0.7236(3) 0.8527(2) 0.7600(2) 0.0732(9) Uani 1 1 d . . . C46 C 0.6956(3) 0.6875(3) 0.9307(2) 0.0865(10) Uani 1 1 d . . . H46A H 0.7330 0.6502 0.9551 0.104 Uiso 1 1 calc R . . H46B H 0.6194 0.6401 0.9078 0.104 Uiso 1 1 calc R . . C49 C 0.6477(3) 0.8808(3) 0.7202(2) 0.0826(9) Uani 1 1 d . . . H49 H 0.5774 0.8557 0.7370 0.099 Uiso 1 1 calc R . . C47 C 0.7526(3) 0.7422(3) 0.8587(2) 0.0919(11) Uani 1 1 d . . . H47A H 0.8270 0.7935 0.8817 0.110 Uiso 1 1 calc R . . H47B H 0.7573 0.6962 0.8141 0.110 Uiso 1 1 calc R . . C53 C 0.8275(3) 0.8882(3) 0.7368(3) 0.0901(10) Uani 1 1 d . . . H53 H 0.8793 0.8696 0.7636 0.108 Uiso 1 1 calc R . . C50 C 0.6732(4) 0.9452(3) 0.6559(3) 0.0968(11) Uani 1 1 d . . . C52 C 0.8535(4) 0.9530(3) 0.6719(3) 0.1122(15) Uani 1 1 d . . . H52 H 0.9241 0.9785 0.6555 0.135 Uiso 1 1 calc R . . C51 C 0.7781(5) 0.9800(3) 0.6317(3) 0.1170(16) Uani 1 1 d . . . H51 H 0.7972 1.0222 0.5876 0.140 Uiso 1 1 calc R . . C54 C 0.5887(5) 0.9748(4) 0.6106(4) 0.159(2) Uani 1 1 d . . . H54A H 0.5621 0.9402 0.5520 0.239 Uiso 1 1 calc R . . H54B H 0.6230 1.0462 0.6078 0.239 Uiso 1 1 calc R . . H54C H 0.5275 0.9569 0.6434 0.239 Uiso 1 1 calc R . . H1N H 0.176(2) 0.3300(19) 0.5028(17) 0.049(8) Uiso 1 1 d . . . H2N H 0.697(2) 0.8105(19) 0.9751(16) 0.049(7) 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 Cl1 0.0708(5) 0.0720(5) 0.0690(5) 0.0213(4) 0.0015(4) 0.0307(4) Cl2 0.1034(7) 0.0725(6) 0.0759(6) 0.0219(5) -0.0041(5) 0.0234(5) N1 0.0777(17) 0.0544(15) 0.0592(16) 0.0123(14) 0.0026(12) 0.0290(13) N2 0.0770(17) 0.0457(13) 0.0646(16) 0.0091(13) -0.0056(12) 0.0259(12) O4 0.0922(14) 0.0478(11) 0.0568(12) 0.0031(10) 0.0014(10) 0.0226(10) O1 0.0706(13) 0.0882(15) 0.0637(13) 0.0037(12) -0.0020(10) 0.0400(11) O2 0.0971(16) 0.0636(13) 0.0685(14) -0.0015(11) -0.0119(11) 0.0386(11) O3 0.0705(13) 0.0679(13) 0.0658(13) 0.0042(11) 0.0099(10) 0.0255(10) O5 0.0835(15) 0.0619(13) 0.0918(16) 0.0059(12) -0.0088(11) 0.0338(11) O6 0.0800(14) 0.0927(16) 0.0689(14) 0.0080(13) 0.0055(11) 0.0439(12) O7 0.133(2) 0.0661(14) 0.0865(16) 0.0202(13) -0.0154(14) 0.0377(13) O10 0.174(3) 0.0634(16) 0.115(2) 0.0098(16) -0.0049(19) 0.0360(16) O9 0.123(2) 0.0892(18) 0.184(3) 0.0384(19) -0.073(2) 0.0281(16) O12 0.324(6) 0.089(2) 0.109(3) 0.010(2) 0.003(3) -0.014(3) O14 0.208(3) 0.0663(15) 0.0711(16) 0.0176(14) 0.0166(17) 0.0288(17) O11 0.123(2) 0.197(4) 0.152(3) 0.102(3) -0.022(2) 0.012(2) O13 0.269(6) 0.329(7) 0.241(5) 0.079(5) 0.135(5) 0.181(6) O8 0.172(4) 0.303(6) 0.180(4) 0.065(4) 0.095(3) 0.136(4) C3 0.072(2) 0.0731(19) 0.0532(17) -0.0139(15) -0.0107(14) 0.0413(16) C4 0.072(2) 0.075(2) 0.0598(18) -0.0086(16) -0.0039(14) 0.0374(16) C5 0.103(3) 0.070(2) 0.064(2) -0.0090(17) -0.0056(17) 0.0436(19) C8 0.075(2) 0.095(2) 0.070(2) -0.0068(18) -0.0008(15) 0.0513(18) C2 0.0658(19) 0.073(2) 0.073(2) -0.0077(17) -0.0034(15) 0.0280(16) C6 0.108(3) 0.084(2) 0.072(2) -0.004(2) -0.006(2) 0.061(2) C1 0.080(2) 0.0531(17) 0.083(2) -0.0068(16) -0.0027(16) 0.0269(15) C9 0.120(3) 0.116(3) 0.107(3) 0.023(3) 0.013(3) 0.046(3) C12 0.0715(19) 0.069(2) 0.0601(18) 0.0013(16) 0.0076(14) 0.0388(15) C13 0.075(2) 0.074(2) 0.0620(19) 0.0016(16) 0.0043(14) 0.0415(16) C11 0.101(2) 0.080(2) 0.0552(18) 0.0044(17) -0.0011(16) 0.0434(18) C14 0.082(2) 0.089(2) 0.076(2) 0.019(2) 0.0149(17) 0.0465(19) C10 0.101(2) 0.076(2) 0.063(2) 0.0187(18) 0.0126(17) 0.0387(18) C17 0.076(2) 0.073(2) 0.0623(19) 0.0057(17) 0.0038(15) 0.0278(16) C16 0.094(3) 0.079(2) 0.086(3) 0.006(2) -0.0008(19) 0.0154(19) C18 0.113(3) 0.115(3) 0.112(3) 0.040(3) 0.009(2) 0.062(3) C15 0.098(3) 0.074(2) 0.102(3) 0.019(2) 0.006(2) 0.024(2) C21 0.0467(16) 0.089(2) 0.0636(19) 0.0058(18) 0.0024(13) 0.0240(15) C22 0.0500(16) 0.095(2) 0.074(2) 0.0226(19) 0.0086(14) 0.0276(16) C20 0.074(2) 0.073(2) 0.090(2) -0.0018(19) -0.0033(17) 0.0376(17) C19 0.078(2) 0.069(2) 0.085(2) 0.0101(18) -0.0066(17) 0.0360(16) C26 0.059(2) 0.124(3) 0.083(3) -0.012(2) 0.0093(18) 0.023(2) C23 0.060(2) 0.128(3) 0.093(3) 0.048(3) 0.0133(19) 0.028(2) C24 0.067(2) 0.183(5) 0.082(3) 0.047(4) 0.012(2) 0.011(3) C25 0.067(2) 0.183(5) 0.078(3) -0.009(4) 0.018(2) 0.021(3) C27 0.104(3) 0.146(4) 0.195(5) 0.104(4) 0.043(3) 0.050(3) C7 0.085(2) 0.098(3) 0.085(2) -0.008(2) -0.0114(19) 0.060(2) C39 0.078(2) 0.068(2) 0.080(2) 0.0001(18) 0.0061(16) 0.0432(17) C40 0.088(2) 0.082(2) 0.087(2) 0.0141(19) 0.0172(18) 0.0551(19) C38 0.073(2) 0.0583(19) 0.109(3) 0.0131(19) 0.0066(18) 0.0225(15) C37 0.088(2) 0.0614(19) 0.081(2) 0.0223(17) 0.0075(18) 0.0268(16) C44 0.085(3) 0.099(3) 0.107(3) -0.005(2) -0.011(2) 0.048(2) C41 0.123(3) 0.109(3) 0.095(3) 0.023(2) 0.019(2) 0.081(3) C42 0.151(5) 0.146(4) 0.102(3) 0.015(3) -0.001(3) 0.112(4) C43 0.103(3) 0.141(4) 0.118(3) -0.011(3) -0.021(3) 0.076(3) C45 0.215(6) 0.124(4) 0.159(5) 0.070(4) 0.042(4) 0.106(4) C31 0.0694(18) 0.0554(17) 0.0525(17) -0.0007(14) 0.0008(13) 0.0209(13) C29 0.081(2) 0.0571(17) 0.0591(18) 0.0085(15) -0.0056(14) 0.0187(15) C30 0.0588(16) 0.0462(15) 0.0603(18) 0.0060(14) 0.0015(12) 0.0173(12) C32 0.0753(19) 0.0553(17) 0.0648(19) 0.0104(16) 0.0031(14) 0.0217(14) C28 0.079(2) 0.0608(18) 0.073(2) 0.0154(16) -0.0131(15) 0.0255(15) C35 0.083(2) 0.0583(18) 0.0578(18) 0.0009(16) 0.0055(14) 0.0275(15) C33 0.096(2) 0.0504(17) 0.088(3) 0.0091(19) 0.0081(18) 0.0284(16) C34 0.108(3) 0.0582(19) 0.074(2) -0.0057(18) 0.0026(18) 0.0320(18) C36 0.135(3) 0.079(2) 0.079(2) 0.024(2) 0.008(2) 0.034(2) C48 0.078(2) 0.074(2) 0.0517(18) -0.0125(16) 0.0090(15) 0.0234(17) C46 0.102(3) 0.066(2) 0.090(3) -0.004(2) -0.009(2) 0.0432(19) C49 0.085(2) 0.078(2) 0.070(2) 0.0067(19) 0.0106(17) 0.0250(18) C47 0.102(3) 0.098(3) 0.084(3) -0.014(2) 0.001(2) 0.058(2) C53 0.084(2) 0.086(2) 0.085(3) -0.015(2) 0.021(2) 0.0256(19) C50 0.110(3) 0.075(2) 0.080(2) 0.007(2) 0.012(2) 0.019(2) C52 0.103(3) 0.088(3) 0.120(4) -0.024(3) 0.053(3) 0.016(2) C51 0.150(5) 0.075(3) 0.099(3) 0.002(2) 0.052(3) 0.020(3) C54 0.169(5) 0.144(4) 0.149(4) 0.078(4) 0.007(4) 0.053(4) _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 Cl1 O8 1.365(4) . ? Cl1 O9 1.393(2) . ? Cl1 O7 1.403(2) . ? Cl1 O10 1.430(3) . ? Cl2 O12 1.318(3) . ? Cl2 O11 1.366(3) . ? Cl2 O14 1.395(2) . ? Cl2 O13 1.433(5) . ? N1 C19 1.490(4) . ? N1 C1 1.498(4) . ? N1 C10 1.499(4) . ? N2 C46 1.497(4) . ? N2 C37 1.498(4) . ? N2 C28 1.515(3) . ? O4 C30 1.382(3) . ? O4 C29 1.428(3) . ? O1 C3 1.384(3) . ? O1 C2 1.419(4) . ? O2 C12 1.373(3) . ? O2 C11 1.435(3) . ? O3 C21 1.367(4) . ? O3 C20 1.425(3) . ? O5 C39 1.380(3) . ? O5 C38 1.422(3) . ? O6 C48 1.387(4) . ? O6 C47 1.430(4) . ? C3 C4 1.378(4) . ? C3 C8 1.388(4) . ? C4 C5 1.389(4) . ? C5 C6 1.392(5) . ? C5 C9 1.525(5) . ? C8 C7 1.386(4) . ? C2 C1 1.491(4) . ? C6 C7 1.363(5) . ? C12 C17 1.385(4) . ? C12 C13 1.389(4) . ? C13 C14 1.378(4) . ? C11 C10 1.498(4) . ? C14 C15 1.376(5) . ? C14 C18 1.508(4) . ? C17 C16 1.374(4) . ? C16 C15 1.368(5) . ? C21 C22 1.375(4) . ? C21 C26 1.389(5) . ? C22 C23 1.377(4) . ? C20 C19 1.490(5) . ? C26 C25 1.380(6) . ? C23 C24 1.405(7) . ? C23 C27 1.504(6) . ? C24 C25 1.364(7) . ? C39 C44 1.372(5) . ? C39 C40 1.379(4) . ? C40 C41 1.366(5) . ? C38 C37 1.500(4) . ? C44 C43 1.392(5) . ? C41 C42 1.379(6) . ? C41 C45 1.504(6) . ? C42 C43 1.343(6) . ? C31 C30 1.377(4) . ? C31 C32 1.384(4) . ? C29 C28 1.492(4) . ? C30 C35 1.376(4) . ? C32 C33 1.382(4) . ? C32 C36 1.503(4) . ? C35 C34 1.388(4) . ? C33 C34 1.371(4) . ? C48 C53 1.365(5) . ? C48 C49 1.373(4) . ? C46 C47 1.487(5) . ? C49 C50 1.381(5) . ? C53 C52 1.392(6) . ? C50 C51 1.383(6) . ? C50 C54 1.520(6) . ? C52 C51 1.360(6) . ? 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 O8 Cl1 O9 111.3(3) . . ? O8 Cl1 O7 111.6(2) . . ? O9 Cl1 O7 109.97(16) . . ? O8 Cl1 O10 106.4(3) . . ? O9 Cl1 O10 108.0(2) . . ? O7 Cl1 O10 109.48(15) . . ? O12 Cl2 O11 117.9(3) . . ? O12 Cl2 O14 113.69(19) . . ? O11 Cl2 O14 112.2(2) . . ? O12 Cl2 O13 101.1(4) . . ? O11 Cl2 O13 98.2(3) . . ? O14 Cl2 O13 112.0(3) . . ? C19 N1 C1 113.8(2) . . ? C19 N1 C10 112.9(2) . . ? C1 N1 C10 113.7(3) . . ? C46 N2 C37 113.9(2) . . ? C46 N2 C28 112.9(3) . . ? C37 N2 C28 113.0(2) . . ? C30 O4 C29 118.3(2) . . ? C3 O1 C2 119.8(2) . . ? C12 O2 C11 118.8(2) . . ? C21 O3 C20 119.3(3) . . ? C39 O5 C38 118.8(2) . . ? C48 O6 C47 119.2(3) . . ? C4 C3 O1 115.8(3) . . ? C4 C3 C8 121.6(3) . . ? O1 C3 C8 122.6(3) . . ? C3 C4 C5 120.5(3) . . ? C4 C5 C6 118.1(3) . . ? C4 C5 C9 120.1(3) . . ? C6 C5 C9 121.8(3) . . ? C7 C8 C3 117.1(3) . . ? O1 C2 C1 105.6(3) . . ? C7 C6 C5 120.6(3) . . ? C2 C1 N1 109.7(2) . . ? O2 C12 C17 124.2(3) . . ? O2 C12 C13 114.8(3) . . ? C17 C12 C13 121.0(3) . . ? C14 C13 C12 120.6(3) . . ? O2 C11 C10 104.1(2) . . ? C15 C14 C13 117.9(3) . . ? C15 C14 C18 122.3(3) . . ? C13 C14 C18 119.7(3) . . ? C11 C10 N1 109.0(3) . . ? C16 C17 C12 117.5(3) . . ? C15 C16 C17 121.6(3) . . ? C16 C15 C14 121.4(3) . . ? O3 C21 C22 115.3(3) . . ? O3 C21 C26 123.5(3) . . ? C22 C21 C26 121.2(3) . . ? C21 C22 C23 122.0(4) . . ? O3 C20 C19 104.9(3) . . ? N1 C19 C20 109.5(2) . . ? C25 C26 C21 117.1(4) . . ? C22 C23 C24 116.4(4) . . ? C22 C23 C27 121.9(4) . . ? C24 C23 C27 121.7(4) . . ? C25 C24 C23 121.5(4) . . ? C24 C25 C26 121.8(5) . . ? C6 C7 C8 122.2(3) . . ? C44 C39 C40 121.1(3) . . ? C44 C39 O5 124.0(3) . . ? C40 C39 O5 114.8(3) . . ? C41 C40 C39 121.1(4) . . ? O5 C38 C37 104.0(2) . . ? N2 C37 C38 108.1(3) . . ? C39 C44 C43 116.8(4) . . ? C40 C41 C42 118.0(4) . . ? C40 C41 C45 120.5(4) . . ? C42 C41 C45 121.5(4) . . ? C43 C42 C41 121.0(4) . . ? C42 C43 C44 122.0(4) . . ? C30 C31 C32 121.4(3) . . ? O4 C29 C28 105.0(2) . . ? C35 C30 C31 120.9(3) . . ? C35 C30 O4 123.7(2) . . ? C31 C30 O4 115.4(3) . . ? C33 C32 C31 117.8(3) . . ? C33 C32 C36 122.0(3) . . ? C31 C32 C36 120.2(3) . . ? C29 C28 N2 109.2(2) . . ? C30 C35 C34 117.6(3) . . ? C34 C33 C32 120.7(3) . . ? C33 C34 C35 121.7(3) . . ? C53 C48 C49 120.5(3) . . ? C53 C48 O6 124.3(3) . . ? C49 C48 O6 115.1(3) . . ? C47 C46 N2 108.7(3) . . ? C48 C49 C50 121.7(4) . . ? O6 C47 C46 105.2(3) . . ? C48 C53 C52 118.0(4) . . ? C49 C50 C51 117.6(4) . . ? C49 C50 C54 121.8(4) . . ? C51 C50 C54 120.6(4) . . ? C51 C52 C53 121.5(4) . . ? C52 C51 C50 120.7(4) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 28.24 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.024 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.042 data_p-cresolBr _database_code_depnum_ccdc_archive 'CCDC 766469' #TrackingRef '- All CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H38 Br N O5' _chemical_formula_weight 536.48 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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' _cell_length_a 43.2178(12) _cell_length_b 7.6050(2) _cell_length_c 17.6312(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.385(3) _cell_angle_gamma 90.00 _cell_volume 5587.2(3) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 9931 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 20.66 _exptl_crystal_description rectangular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2256 _exptl_absorpt_coefficient_mu 1.506 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.623 _exptl_absorpt_correction_T_max 0.696 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 43040 _diffrn_reflns_av_R_equivalents 0.0938 _diffrn_reflns_av_sigmaI/netI 0.0843 _diffrn_reflns_limit_h_min -57 _diffrn_reflns_limit_h_max 57 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 0.98 _diffrn_reflns_theta_max 28.34 _reflns_number_total 6964 _reflns_number_gt 6598 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0655P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6964 _refine_ls_number_parameters 330 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.1051 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.1094 _refine_ls_wR_factor_gt 0.0861 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.941 _refine_ls_shift/su_max 0.002 _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 Br1 Br 0.244667(9) 0.97096(5) 0.143684(19) 0.07386(17) Uani 1 1 d . . . N1 N 0.19356(6) 0.9399(3) 0.39091(14) 0.0495(6) Uani 1 1 d . . . C2 C 0.17668(7) 1.2474(4) 0.37228(19) 0.0645(8) Uani 1 1 d . . . H2A H 0.1804 1.3668 0.3918 0.077 Uiso 1 1 calc R . . H2B H 0.1788 1.2434 0.3189 0.077 Uiso 1 1 calc R . . C1 C 0.19968(7) 1.1224(4) 0.42428(18) 0.0608(8) Uani 1 1 d . . . H1A H 0.1968 1.1250 0.4770 0.073 Uiso 1 1 calc R . . H1B H 0.2216 1.1570 0.4273 0.073 Uiso 1 1 calc R . . O1 O 0.14575(4) 1.1875(3) 0.37517(11) 0.0595(5) Uani 1 1 d . . . C3 C 0.11893(7) 1.2371(4) 0.31754(16) 0.0501(7) Uani 1 1 d . . . C4 C 0.09029(7) 1.1812(4) 0.32953(17) 0.0560(8) Uani 1 1 d . . . H4 H 0.0902 1.1185 0.3747 0.067 Uiso 1 1 calc R . . C8 C 0.11913(7) 1.3301(4) 0.25082(17) 0.0594(8) Uani 1 1 d . . . H8 H 0.1383 1.3693 0.2423 0.071 Uiso 1 1 calc R . . C5 C 0.06186(7) 1.2181(4) 0.27473(18) 0.0640(9) Uani 1 1 d . . . H5 H 0.0427 1.1799 0.2835 0.077 Uiso 1 1 calc R . . C7 C 0.09017(9) 1.3643(4) 0.19659(18) 0.0692(9) Uani 1 1 d . . . H7 H 0.0903 1.4262 0.1512 0.083 Uiso 1 1 calc R . . C6 C 0.06123(8) 1.3107(4) 0.20687(17) 0.0646(9) Uani 1 1 d . . . C9 C 0.02982(8) 1.3483(6) 0.1466(2) 0.1039(14) Uani 1 1 d . . . H9A H 0.0151 1.4008 0.1721 0.156 Uiso 1 1 calc R . . H9B H 0.0210 1.2404 0.1219 0.156 Uiso 1 1 calc R . . H9C H 0.0335 1.4276 0.1075 0.156 Uiso 1 1 calc R . . C12 C 0.11459(7) 0.7442(4) 0.42241(17) 0.0527(7) Uani 1 1 d . . . C17 C 0.09216(7) 0.7038(4) 0.35341(17) 0.0602(8) Uani 1 1 d . . . H17 H 0.0986 0.6599 0.3109 0.072 Uiso 1 1 calc R . . C11 C 0.17133(7) 0.7811(4) 0.48557(17) 0.0657(9) Uani 1 1 d . . . H11A H 0.1754 0.6962 0.5281 0.079 Uiso 1 1 calc R . . H11B H 0.1658 0.8930 0.5049 0.079 Uiso 1 1 calc R . . C13 C 0.10502(8) 0.8027(4) 0.48651(18) 0.0654(9) Uani 1 1 d . . . H13 H 0.1199 0.8263 0.5341 0.078 Uiso 1 1 calc R . . C10 C 0.20008(7) 0.7997(4) 0.45357(18) 0.0642(9) Uani 1 1 d . . . H10A H 0.2045 0.6887 0.4314 0.077 Uiso 1 1 calc R . . H10B H 0.2187 0.8316 0.4956 0.077 Uiso 1 1 calc R . . C14 C 0.07248(9) 0.8255(4) 0.4779(2) 0.0759(10) Uani 1 1 d . . . H14 H 0.0659 0.8654 0.5210 0.091 Uiso 1 1 calc R . . C15 C 0.04970(8) 0.7924(4) 0.4096(2) 0.0745(10) Uani 1 1 d . . . C16 C 0.05997(8) 0.7287(4) 0.3475(2) 0.0693(9) Uani 1 1 d . . . H16 H 0.0449 0.7017 0.3005 0.083 Uiso 1 1 calc R . . C18 C 0.01425(8) 0.8225(5) 0.4027(3) 0.1151(15) Uani 1 1 d . . . H18A H 0.0034 0.7113 0.3977 0.173 Uiso 1 1 calc R . . H18B H 0.0051 0.8931 0.3571 0.173 Uiso 1 1 calc R . . H18C H 0.0119 0.8820 0.4489 0.173 Uiso 1 1 calc R . . O2 O 0.14611(5) 0.7216(3) 0.42052(11) 0.0641(6) Uani 1 1 d . . . C24 C 0.08372(7) 0.7251(4) 0.05047(16) 0.0516(7) Uani 1 1 d . . . C22 C 0.10420(7) 0.8757(4) 0.17424(16) 0.0519(7) Uani 1 1 d . . . H22 H 0.1003 0.9428 0.2148 0.062 Uiso 1 1 calc R . . C21 C 0.13507(7) 0.8279(4) 0.17549(16) 0.0506(7) Uani 1 1 d . . . C23 C 0.07914(7) 0.8232(4) 0.11240(16) 0.0539(7) Uani 1 1 d . . . H23 H 0.0584 0.8551 0.1124 0.065 Uiso 1 1 calc R . . C25 C 0.11484(7) 0.6804(4) 0.05288(17) 0.0630(8) Uani 1 1 d . . . H25 H 0.1187 0.6152 0.0117 0.076 Uiso 1 1 calc R . . C26 C 0.14051(7) 0.7294(4) 0.11472(18) 0.0628(8) Uani 1 1 d . . . H26 H 0.1613 0.6961 0.1152 0.075 Uiso 1 1 calc R . . C20 C 0.18852(6) 0.7959(4) 0.26239(17) 0.0613(8) Uani 1 1 d . . . H20A H 0.1979 0.7832 0.2185 0.074 Uiso 1 1 calc R . . H20B H 0.1854 0.6800 0.2820 0.074 Uiso 1 1 calc R . . C27 C 0.05583(7) 0.6695(4) -0.01648(17) 0.0725(9) Uani 1 1 d . . . H27A H 0.0449 0.7719 -0.0421 0.109 Uiso 1 1 calc R . . H27B H 0.0413 0.5997 0.0036 0.109 Uiso 1 1 calc R . . H27C H 0.0636 0.6016 -0.0535 0.109 Uiso 1 1 calc R . . C19 C 0.20968(7) 0.9058(5) 0.32624(18) 0.0628(8) Uani 1 1 d . . . H19A H 0.2143 1.0169 0.3044 0.075 Uiso 1 1 calc R . . H19B H 0.2299 0.8454 0.3477 0.075 Uiso 1 1 calc R . . O3 O 0.15884(4) 0.8889(3) 0.23901(11) 0.0638(6) Uani 1 1 d . . . O4 O 0.21581(6) 0.4274(4) 0.57076(16) 0.0853(7) Uani 1 1 d D . . O5 O 0.20636(7) 0.6673(4) 0.68827(16) 0.0903(7) Uani 1 1 d D . . H1N H 0.1720(6) 0.936(3) 0.3699(13) 0.035(7) Uiso 1 1 d . . . H1O H 0.2134(9) 0.499(4) 0.6097(15) 0.096(14) Uiso 1 1 d D . . H2O H 0.2258(8) 0.329(3) 0.593(2) 0.126(17) Uiso 1 1 d D . . H3O H 0.2210(7) 0.641(5) 0.7337(12) 0.115(15) Uiso 1 1 d D . . H4O H 0.2147(9) 0.771(3) 0.678(2) 0.125(18) Uiso 1 1 d 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 Br1 0.0889(3) 0.0684(3) 0.0615(2) 0.00225(17) 0.01499(19) -0.01158(19) N1 0.0342(14) 0.0564(17) 0.0525(15) -0.0038(12) 0.0020(12) 0.0011(12) C2 0.060(2) 0.055(2) 0.078(2) -0.0012(17) 0.0163(17) -0.0061(16) C1 0.0485(17) 0.061(2) 0.068(2) -0.0095(17) 0.0062(15) -0.0054(16) O1 0.0515(12) 0.0658(14) 0.0606(13) 0.0127(10) 0.0142(10) 0.0065(10) C3 0.0580(19) 0.0426(18) 0.0502(17) -0.0008(14) 0.0153(15) 0.0069(14) C4 0.063(2) 0.055(2) 0.0542(18) 0.0075(15) 0.0227(16) 0.0124(16) C8 0.066(2) 0.052(2) 0.062(2) 0.0102(16) 0.0193(17) 0.0002(16) C5 0.0549(19) 0.071(2) 0.067(2) 0.0034(17) 0.0178(17) 0.0097(16) C7 0.092(3) 0.056(2) 0.058(2) 0.0138(16) 0.0163(19) 0.0071(19) C6 0.068(2) 0.064(2) 0.056(2) 0.0055(16) 0.0067(17) 0.0166(17) C9 0.086(3) 0.123(4) 0.089(3) 0.022(3) 0.000(2) 0.019(2) C12 0.062(2) 0.0437(18) 0.0550(19) 0.0051(14) 0.0199(16) -0.0029(15) C17 0.072(2) 0.057(2) 0.0519(19) -0.0012(15) 0.0165(17) -0.0017(17) C11 0.071(2) 0.069(2) 0.0504(18) 0.0117(16) 0.0053(17) 0.0046(18) C13 0.084(2) 0.062(2) 0.0520(19) -0.0079(16) 0.0212(17) -0.0170(18) C10 0.0563(19) 0.063(2) 0.0605(19) 0.0048(16) -0.0078(15) 0.0121(16) C14 0.087(3) 0.065(2) 0.091(3) -0.013(2) 0.051(2) -0.016(2) C15 0.073(2) 0.056(2) 0.100(3) -0.005(2) 0.032(2) -0.0084(18) C16 0.068(2) 0.063(2) 0.073(2) -0.0015(18) 0.0115(18) -0.0047(18) C18 0.075(3) 0.102(3) 0.182(4) -0.023(3) 0.058(3) -0.008(2) O2 0.0614(13) 0.0703(15) 0.0568(13) -0.0083(11) 0.0089(11) -0.0043(11) C24 0.0606(19) 0.0488(19) 0.0436(16) 0.0032(14) 0.0108(14) -0.0017(15) C22 0.0529(18) 0.057(2) 0.0452(16) -0.0047(14) 0.0128(14) 0.0045(15) C21 0.0506(18) 0.0538(19) 0.0438(16) -0.0018(14) 0.0063(14) 0.0032(14) C23 0.0496(17) 0.057(2) 0.0546(18) 0.0030(15) 0.0137(15) 0.0043(14) C25 0.073(2) 0.066(2) 0.0508(19) -0.0138(16) 0.0179(17) 0.0021(17) C26 0.0554(18) 0.075(2) 0.0596(19) -0.0115(17) 0.0179(16) 0.0103(17) C20 0.0443(17) 0.079(2) 0.0601(19) -0.0078(17) 0.0130(14) 0.0094(16) C27 0.078(2) 0.077(2) 0.059(2) -0.0036(17) 0.0101(17) -0.0134(19) C19 0.0427(17) 0.078(2) 0.068(2) -0.0052(17) 0.0148(15) 0.0019(16) O3 0.0518(12) 0.0733(14) 0.0589(13) -0.0162(11) 0.0018(10) 0.0123(11) O4 0.0839(18) 0.085(2) 0.0822(19) -0.0014(17) 0.0131(15) 0.0094(16) O5 0.094(2) 0.091(2) 0.0778(19) 0.0016(16) 0.0100(16) 0.0033(17) _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 N1 C1 1.503(4) . ? N1 C10 1.507(4) . ? N1 C19 1.508(4) . ? C2 O1 1.426(3) . ? C2 C1 1.499(4) . ? O1 C3 1.376(3) . ? C3 C8 1.375(4) . ? C3 C4 1.377(4) . ? C4 C5 1.375(4) . ? C8 C7 1.383(4) . ? C5 C6 1.383(4) . ? C7 C6 1.372(4) . ? C6 C9 1.513(4) . ? C12 C17 1.374(4) . ? C12 C13 1.376(4) . ? C12 O2 1.382(3) . ? C17 C16 1.380(4) . ? C11 O2 1.430(3) . ? C11 C10 1.501(4) . ? C13 C14 1.385(4) . ? C14 C15 1.362(4) . ? C15 C16 1.375(5) . ? C15 C18 1.521(4) . ? C24 C25 1.377(4) . ? C24 C23 1.379(4) . ? C24 C27 1.507(4) . ? C22 C23 1.376(4) . ? C22 C21 1.377(4) . ? C21 C26 1.378(4) . ? C21 O3 1.384(3) . ? C25 C26 1.384(4) . ? C20 O3 1.426(3) . ? C20 C19 1.502(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C10 112.8(2) . . ? C1 N1 C19 112.7(2) . . ? C10 N1 C19 113.5(2) . . ? O1 C2 C1 104.6(2) . . ? C2 C1 N1 109.1(2) . . ? C3 O1 C2 120.0(2) . . ? C8 C3 O1 125.3(3) . . ? C8 C3 C4 120.0(3) . . ? O1 C3 C4 114.7(2) . . ? C5 C4 C3 120.1(3) . . ? C3 C8 C7 118.6(3) . . ? C4 C5 C6 121.4(3) . . ? C6 C7 C8 122.8(3) . . ? C7 C6 C5 117.1(3) . . ? C7 C6 C9 122.1(3) . . ? C5 C6 C9 120.8(3) . . ? C17 C12 C13 120.3(3) . . ? C17 C12 O2 114.8(3) . . ? C13 C12 O2 124.9(3) . . ? C12 C17 C16 119.8(3) . . ? O2 C11 C10 105.0(2) . . ? C12 C13 C14 117.9(3) . . ? C11 C10 N1 109.3(2) . . ? C15 C14 C13 123.3(3) . . ? C14 C15 C16 117.3(3) . . ? C14 C15 C18 121.3(4) . . ? C16 C15 C18 121.4(4) . . ? C15 C16 C17 121.3(3) . . ? C12 O2 C11 119.2(2) . . ? C25 C24 C23 117.0(3) . . ? C25 C24 C27 121.8(3) . . ? C23 C24 C27 121.2(3) . . ? C23 C22 C21 119.4(3) . . ? C22 C21 C26 119.7(3) . . ? C22 C21 O3 115.6(2) . . ? C26 C21 O3 124.7(3) . . ? C22 C23 C24 122.4(3) . . ? C24 C25 C26 122.0(3) . . ? C21 C26 C25 119.5(3) . . ? O3 C20 C19 105.2(2) . . ? C20 C19 N1 110.5(2) . . ? C21 O3 C20 119.0(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.348 _refine_diff_density_min -0.554 _refine_diff_density_rms 0.144 data_p-CresolPic _database_code_depnum_ccdc_archive 'CCDC 766470' #TrackingRef 'all cif.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H36 N4 O10' _chemical_formula_weight 648.61 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 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0888(3) _cell_length_b 12.3654(4) _cell_length_c 13.7716(4) _cell_angle_alpha 81.260(2) _cell_angle_beta 76.965(2) _cell_angle_gamma 83.641(1) _cell_volume 1649.10(9) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3566 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description rectangular _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.966 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_process_details 'SADAS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 18236 _diffrn_reflns_av_R_equivalents 0.0643 _diffrn_reflns_av_sigmaI/netI 0.0718 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 28.35 _reflns_number_total 7968 _reflns_number_gt 7776 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0776P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method None _refine_ls_extinction_coef ? _refine_ls_number_reflns 7568 _refine_ls_number_parameters 432 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0958 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1646 _refine_ls_wR_factor_gt 0.1454 _refine_ls_goodness_of_fit_ref 0.924 _refine_ls_restrained_S_all 0.924 _refine_ls_shift/su_max 0.019 _refine_ls_shift/su_mean 0.569 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 C31 C 0.1034(2) 0.48810(16) 0.83973(15) 0.0460(5) Uani 1 1 d . . . C33 C 0.0889(2) 0.64151(16) 0.92562(16) 0.0505(5) Uani 1 1 d . . . C29 C 0.2338(2) 0.48425(17) 0.96332(16) 0.0511(5) Uani 1 1 d . . . C30 C 0.1981(2) 0.43449(17) 0.89182(15) 0.0512(5) Uani 1 1 d . . . H30 H 0.2374 0.3652 0.8786 0.061 Uiso 1 1 calc R . . C32 C 0.0478(2) 0.59198(17) 0.85590(15) 0.0519(5) Uani 1 1 d . . . H32 H -0.0161 0.6279 0.8204 0.062 Uiso 1 1 calc R . . N3 N 0.05831(19) 0.43323(16) 0.76847(14) 0.0558(5) Uani 1 1 d . . . N2 N 0.3281(3) 0.42179(19) 1.0195(2) 0.0803(7) Uani 1 1 d . . . N4 N 0.0289(3) 0.75195(18) 0.94003(17) 0.0770(6) Uani 1 1 d . . . O7 O 0.09435(17) 0.33500(13) 0.76640(13) 0.0744(5) Uani 1 1 d . . . O8 O -0.01385(18) 0.48532(14) 0.71492(13) 0.0741(5) Uani 1 1 d . . . O9 O -0.0960(2) 0.77067(16) 0.94544(15) 0.0974(6) Uani 1 1 d . . . O10 O 0.0976(3) 0.82027(17) 0.9481(2) 0.1394(10) Uani 1 1 d . . . O5 O 0.3035(3) 0.4202(2) 1.10983(19) 0.1201(8) Uani 1 1 d . . . O6 O 0.4233(3) 0.3719(3) 0.9755(2) 0.1708(14) Uani 1 1 d . . . C12 C 0.4939(2) 0.47027(18) 0.67984(17) 0.0571(6) Uani 1 1 d . . . C13 C 0.4982(3) 0.5650(2) 0.7189(2) 0.0847(8) Uani 1 1 d . . . H13 H 0.5601 0.5684 0.7590 0.102 Uiso 1 1 calc R . . C17 C 0.4005(3) 0.4680(2) 0.62260(19) 0.0721(7) Uani 1 1 d . . . H17 H 0.3956 0.4044 0.5957 0.087 Uiso 1 1 calc R . . C15 C 0.3174(3) 0.6554(2) 0.6410(2) 0.0770(8) Uani 1 1 d . . . C14 C 0.4112(3) 0.6553(2) 0.6986(3) 0.0912(9) Uani 1 1 d . . . H14 H 0.4164 0.7190 0.7254 0.109 Uiso 1 1 calc R . . C16 C 0.3138(3) 0.5584(3) 0.6043(2) 0.0826(8) Uani 1 1 d . . . H16 H 0.2503 0.5541 0.5657 0.099 Uiso 1 1 calc R . . C18 C 0.2220(3) 0.7547(3) 0.6219(3) 0.1230(13) Uani 1 1 d . . . H18A H 0.2500 0.8163 0.6448 0.184 Uiso 1 1 calc R . . H18B H 0.1309 0.7405 0.6576 0.184 Uiso 1 1 calc R . . H18C H 0.2240 0.7706 0.5512 0.184 Uiso 1 1 calc R . . O2 O 0.57483(17) 0.37471(12) 0.69559(13) 0.0699(5) Uani 1 1 d . . . C10 C 0.7835(2) 0.27428(19) 0.72204(17) 0.0636(6) Uani 1 1 d . . . H10A H 0.7536 0.2299 0.6799 0.076 Uiso 1 1 calc R . . H10B H 0.8793 0.2847 0.6946 0.076 Uiso 1 1 calc R . . C11 C 0.7034(3) 0.38447(19) 0.7177(2) 0.0678(7) Uani 1 1 d . . . H11A H 0.6900 0.4121 0.7818 0.081 Uiso 1 1 calc R . . H11B H 0.7537 0.4362 0.6663 0.081 Uiso 1 1 calc R . . N1 N 0.76868(18) 0.21318(14) 0.82642(14) 0.0532(5) Uani 1 1 d . . . C21 C 0.8450(2) -0.06190(18) 0.65758(17) 0.0536(5) Uani 1 1 d . . . C26 C 0.8301(2) -0.16567(18) 0.71082(17) 0.0583(6) Uani 1 1 d . . . H26 H 0.8231 -0.1765 0.7801 0.070 Uiso 1 1 calc R . . C25 C 0.8257(2) -0.25297(19) 0.66025(18) 0.0616(6) Uani 1 1 d . . . H25 H 0.8141 -0.3224 0.6965 0.074 Uiso 1 1 calc R . . C22 C 0.8531(2) -0.0469(2) 0.55539(18) 0.0626(6) Uani 1 1 d . . . H22 H 0.8602 0.0229 0.5193 0.075 Uiso 1 1 calc R . . C24 C 0.8380(3) -0.2401(2) 0.55763(18) 0.0655(6) Uani 1 1 d . . . C23 C 0.8505(3) -0.1366(2) 0.50672(18) 0.0719(7) Uani 1 1 d . . . H23 H 0.8574 -0.1261 0.4375 0.086 Uiso 1 1 calc R . . C27 C 0.8372(4) -0.3398(3) 0.5045(2) 0.1058(11) Uani 1 1 d . . . H27A H 0.9142 -0.3904 0.5133 0.159 Uiso 1 1 calc R . . H27B H 0.8424 -0.3165 0.4341 0.159 Uiso 1 1 calc R . . H27C H 0.7545 -0.3752 0.5327 0.159 Uiso 1 1 calc R . . O3 O 0.85227(17) 0.03121(12) 0.69964(11) 0.0648(4) Uani 1 1 d . . . C19 C 0.8793(2) 0.12256(18) 0.83415(18) 0.0596(6) Uani 1 1 d . . . H19A H 0.8900 0.1088 0.9033 0.071 Uiso 1 1 calc R . . H19B H 0.9643 0.1481 0.7932 0.071 Uiso 1 1 calc R . . C20 C 0.8580(3) 0.01519(18) 0.80281(17) 0.0639(6) Uani 1 1 d . . . H20A H 0.9325 -0.0387 0.8138 0.077 Uiso 1 1 calc R . . H20B H 0.7736 -0.0123 0.8430 0.077 Uiso 1 1 calc R . . C3 C 0.6252(2) 0.01602(17) 1.11320(17) 0.0537(5) Uani 1 1 d . . . C4 C 0.6883(2) -0.08493(19) 1.14343(19) 0.0656(6) Uani 1 1 d . . . H4 H 0.7519 -0.1214 1.0968 0.079 Uiso 1 1 calc R . . C8 C 0.5352(2) 0.07084(18) 1.18359(17) 0.0588(6) Uani 1 1 d . . . H8 H 0.4938 0.1394 1.1645 0.071 Uiso 1 1 calc R . . C6 C 0.5643(2) -0.0782(2) 1.31446(18) 0.0636(6) Uani 1 1 d . . . C7 C 0.5067(2) 0.02349(19) 1.28286(19) 0.0623(6) Uani 1 1 d . . . H7 H 0.4464 0.0617 1.3299 0.075 Uiso 1 1 calc R . . C5 C 0.6569(3) -0.1310(2) 1.2423(2) 0.0710(7) Uani 1 1 d . . . H5 H 0.6987 -0.1994 1.2614 0.085 Uiso 1 1 calc R . . C9 C 0.5242(3) -0.1320(2) 1.4223(2) 0.0921(9) Uani 1 1 d . . . H9A H 0.4976 -0.2044 1.4230 0.138 Uiso 1 1 calc R . . H9B H 0.4492 -0.0889 1.4580 0.138 Uiso 1 1 calc R . . H9C H 0.6005 -0.1369 1.4541 0.138 Uiso 1 1 calc R . . O1 O 0.65605(16) 0.05221(12) 1.01171(12) 0.0643(4) Uani 1 1 d . . . C1 C 0.6253(2) 0.17976(18) 0.86745(17) 0.0580(6) Uani 1 1 d . . . H1A H 0.5618 0.2384 0.8460 0.070 Uiso 1 1 calc R . . H1B H 0.6143 0.1154 0.8385 0.070 Uiso 1 1 calc R . . C2 C 0.5886(2) 0.15465(18) 0.97962(17) 0.0602(6) Uani 1 1 d . . . H2A H 0.6152 0.2126 1.0097 0.072 Uiso 1 1 calc R . . H2B H 0.4906 0.1514 1.0016 0.072 Uiso 1 1 calc R . . C28 C 0.1807(2) 0.59179(17) 0.98760(16) 0.0495(5) Uani 1 1 d . . . O4 O 0.20916(17) 0.63467(13) 1.05658(12) 0.0714(5) Uani 1 1 d . . . H1N H 0.784(3) 0.265(2) 0.8622(19) 0.090(9) 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 C31 0.0492(11) 0.0475(12) 0.0453(12) -0.0168(9) -0.0100(10) -0.0058(9) C33 0.0637(13) 0.0378(11) 0.0519(13) -0.0136(9) -0.0123(11) -0.0018(10) C29 0.0540(12) 0.0501(12) 0.0529(13) -0.0136(10) -0.0176(10) 0.0024(10) C30 0.0573(13) 0.0439(12) 0.0549(13) -0.0196(10) -0.0102(10) -0.0005(10) C32 0.0598(13) 0.0465(12) 0.0529(13) -0.0133(10) -0.0166(10) -0.0001(10) N3 0.0582(11) 0.0547(12) 0.0594(12) -0.0221(10) -0.0127(10) -0.0047(9) N2 0.0941(17) 0.0767(15) 0.0817(17) -0.0336(13) -0.0425(14) 0.0248(13) N4 0.1066(18) 0.0532(13) 0.0838(16) -0.0231(11) -0.0460(14) 0.0119(13) O7 0.0902(12) 0.0539(10) 0.0923(13) -0.0364(9) -0.0340(10) 0.0040(9) O8 0.0881(12) 0.0705(11) 0.0796(12) -0.0260(9) -0.0453(10) 0.0050(10) O9 0.1209(18) 0.0757(13) 0.0931(14) -0.0207(10) -0.0314(13) 0.0339(12) O10 0.190(3) 0.0567(13) 0.212(3) -0.0442(15) -0.112(2) -0.0019(14) O5 0.155(2) 0.127(2) 0.0953(17) -0.0176(14) -0.0716(16) 0.0120(16) O6 0.174(2) 0.190(3) 0.164(2) -0.086(2) -0.093(2) 0.123(2) C12 0.0625(14) 0.0523(14) 0.0592(14) -0.0013(11) -0.0188(11) -0.0120(11) C13 0.093(2) 0.0611(17) 0.118(2) -0.0170(16) -0.0591(18) -0.0033(15) C17 0.0741(16) 0.0744(18) 0.0740(17) -0.0140(13) -0.0243(14) -0.0087(14) C15 0.0549(15) 0.0732(18) 0.092(2) 0.0177(15) -0.0108(14) -0.0083(13) C14 0.090(2) 0.0536(16) 0.138(3) -0.0182(16) -0.036(2) -0.0057(15) C16 0.0698(17) 0.102(2) 0.0800(19) -0.0062(16) -0.0274(14) -0.0086(17) C18 0.087(2) 0.099(3) 0.157(3) 0.033(2) -0.013(2) 0.0127(18) O2 0.0796(11) 0.0504(10) 0.0927(12) -0.0117(8) -0.0427(10) -0.0073(8) C10 0.0722(15) 0.0557(14) 0.0656(16) -0.0080(12) -0.0190(12) -0.0065(12) C11 0.0761(16) 0.0498(14) 0.0856(18) -0.0040(12) -0.0344(14) -0.0112(12) N1 0.0639(12) 0.0411(10) 0.0611(12) -0.0147(9) -0.0191(9) -0.0088(8) C21 0.0536(13) 0.0479(13) 0.0614(14) -0.0167(11) -0.0129(10) 0.0015(10) C26 0.0718(15) 0.0533(14) 0.0538(14) -0.0143(11) -0.0222(11) 0.0059(11) C25 0.0716(15) 0.0472(13) 0.0720(16) -0.0126(11) -0.0267(12) 0.0001(11) C22 0.0678(15) 0.0620(15) 0.0572(15) -0.0027(11) -0.0119(12) -0.0113(12) C24 0.0771(16) 0.0669(16) 0.0605(16) -0.0199(12) -0.0235(13) -0.0061(13) C23 0.0814(17) 0.088(2) 0.0515(14) -0.0148(14) -0.0148(13) -0.0184(15) C27 0.155(3) 0.089(2) 0.091(2) -0.0404(17) -0.039(2) -0.020(2) O3 0.0905(11) 0.0463(9) 0.0603(10) -0.0125(7) -0.0198(8) -0.0010(8) C19 0.0633(14) 0.0528(13) 0.0683(15) -0.0162(11) -0.0229(11) 0.0009(11) C20 0.0816(16) 0.0488(13) 0.0648(16) -0.0180(11) -0.0214(12) 0.0070(11) C3 0.0563(13) 0.0450(12) 0.0610(15) -0.0132(11) -0.0092(11) -0.0067(10) C4 0.0657(15) 0.0576(15) 0.0713(17) -0.0205(12) -0.0086(12) 0.0093(12) C8 0.0641(14) 0.0468(13) 0.0671(16) -0.0167(11) -0.0139(12) 0.0011(11) C6 0.0617(14) 0.0653(15) 0.0675(16) -0.0143(12) -0.0193(12) -0.0022(12) C7 0.0573(14) 0.0627(15) 0.0706(17) -0.0243(12) -0.0131(12) 0.0000(11) C5 0.0747(16) 0.0583(15) 0.0786(19) -0.0101(13) -0.0207(14) 0.0120(12) C9 0.102(2) 0.098(2) 0.0712(19) -0.0058(16) -0.0176(16) 0.0008(17) O1 0.0770(10) 0.0468(9) 0.0656(11) -0.0129(7) -0.0085(8) 0.0036(7) C1 0.0615(14) 0.0478(13) 0.0695(16) -0.0141(11) -0.0189(12) -0.0067(10) C2 0.0671(14) 0.0449(13) 0.0682(16) -0.0130(11) -0.0110(12) -0.0025(11) C28 0.0547(12) 0.0478(12) 0.0489(12) -0.0130(10) -0.0103(10) -0.0083(10) O4 0.0946(12) 0.0651(10) 0.0696(11) -0.0299(8) -0.0343(9) -0.0076(9) _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 C31 C30 1.375(3) . ? C31 C32 1.373(3) . ? C31 N3 1.450(2) . ? C33 C32 1.372(3) . ? C33 C28 1.427(3) . ? C33 N4 1.454(3) . ? C29 C30 1.368(3) . ? C29 C28 1.437(3) . ? C29 N2 1.445(3) . ? N3 O8 1.218(2) . ? N3 O7 1.231(2) . ? N2 O6 1.179(3) . ? N2 O5 1.210(3) . ? N4 O10 1.183(3) . ? N4 O9 1.243(3) . ? C12 C17 1.363(3) . ? C12 C13 1.370(3) . ? C12 O2 1.378(3) . ? C13 C14 1.376(4) . ? C17 C16 1.369(4) . ? C15 C14 1.365(4) . ? C15 C16 1.378(4) . ? C15 C18 1.502(4) . ? O2 C11 1.419(3) . ? C10 N1 1.503(3) . ? C10 C11 1.506(3) . ? N1 C19 1.501(3) . ? N1 C1 1.509(3) . ? C21 C22 1.376(3) . ? C21 C26 1.383(3) . ? C21 O3 1.381(2) . ? C26 C25 1.380(3) . ? C25 C24 1.377(3) . ? C22 C23 1.386(3) . ? C24 C23 1.367(3) . ? C24 C27 1.528(3) . ? O3 C20 1.418(3) . ? C19 C20 1.508(3) . ? C3 C8 1.375(3) . ? C3 O1 1.377(3) . ? C3 C4 1.387(3) . ? C4 C5 1.374(3) . ? C8 C7 1.383(3) . ? C6 C7 1.376(3) . ? C6 C5 1.390(3) . ? C6 C9 1.517(4) . ? O1 C2 1.428(3) . ? C1 C2 1.497(3) . ? C28 O4 1.255(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C30 C31 C32 121.10(18) . . ? C30 C31 N3 119.67(18) . . ? C32 C31 N3 119.2(2) . . ? C32 C33 C28 125.29(19) . . ? C32 C33 N4 116.9(2) . . ? C28 C33 N4 117.74(18) . . ? C30 C29 C28 124.3(2) . . ? C30 C29 N2 116.92(19) . . ? C28 C29 N2 118.71(19) . . ? C29 C30 C31 119.28(19) . . ? C33 C32 C31 118.4(2) . . ? O8 N3 O7 123.36(18) . . ? O8 N3 C31 119.03(18) . . ? O7 N3 C31 117.6(2) . . ? O6 N2 O5 123.0(3) . . ? O6 N2 C29 118.4(2) . . ? O5 N2 C29 118.6(2) . . ? O10 N4 O9 121.9(2) . . ? O10 N4 C33 120.3(3) . . ? O9 N4 C33 117.8(2) . . ? C17 C12 C13 118.3(2) . . ? C17 C12 O2 116.5(2) . . ? C13 C12 O2 125.2(2) . . ? C12 C13 C14 120.0(3) . . ? C12 C17 C16 120.8(2) . . ? C14 C15 C16 115.8(3) . . ? C14 C15 C18 121.5(3) . . ? C16 C15 C18 122.6(3) . . ? C15 C14 C13 122.8(3) . . ? C17 C16 C15 122.3(3) . . ? C12 O2 C11 117.15(16) . . ? N1 C10 C11 113.57(19) . . ? O2 C11 C10 109.92(18) . . ? C19 N1 C10 112.39(17) . . ? C19 N1 C1 115.05(17) . . ? C10 N1 C1 111.35(17) . . ? C22 C21 C26 119.6(2) . . ? C22 C21 O3 115.8(2) . . ? C26 C21 O3 124.6(2) . . ? C21 C26 C25 119.4(2) . . ? C24 C25 C26 121.8(2) . . ? C21 C22 C23 119.5(2) . . ? C23 C24 C25 117.8(2) . . ? C23 C24 C27 122.2(2) . . ? C25 C24 C27 119.9(2) . . ? C24 C23 C22 121.8(2) . . ? C21 O3 C20 116.29(17) . . ? N1 C19 C20 116.28(18) . . ? O3 C20 C19 109.53(19) . . ? C8 C3 O1 124.8(2) . . ? C8 C3 C4 119.4(2) . . ? O1 C3 C4 115.83(19) . . ? C5 C4 C3 120.0(2) . . ? C3 C8 C7 119.6(2) . . ? C7 C6 C5 117.0(2) . . ? C7 C6 C9 121.4(2) . . ? C5 C6 C9 121.5(2) . . ? C6 C7 C8 122.3(2) . . ? C4 C5 C6 121.7(2) . . ? C3 O1 C2 116.18(16) . . ? C2 C1 N1 114.27(18) . . ? O1 C2 C1 110.10(17) . . ? O4 C28 C33 124.69(19) . . ? O4 C28 C29 123.9(2) . . ? C33 C28 C29 111.41(18) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.354 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.038 data_o-CresolPic _database_code_depnum_ccdc_archive 'CCDC 766471' #TrackingRef 'all cif.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H36 N4 O10' _chemical_formula_weight 648.66 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 Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.890(2) _cell_length_b 28.388(6) _cell_length_c 11.602(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.896(9) _cell_angle_gamma 90.00 _cell_volume 3253.2(12) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2122 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 18.89 _exptl_crystal_description rectangular _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.966 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_process_details 'SADAS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 41904 _diffrn_reflns_av_R_equivalents 0.1158 _diffrn_reflns_av_sigmaI/netI 0.1365 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 28.48 _reflns_number_total 8066 _reflns_number_gt 7814 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0715P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8066 _refine_ls_number_parameters 432 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1760 _refine_ls_R_factor_gt 0.0551 _refine_ls_wR_factor_ref 0.1537 _refine_ls_wR_factor_gt 0.1256 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.083 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.0263(2) 0.11423(8) 0.81071(17) 0.0589(6) Uani 1 1 d . . . C1 C -0.0057(3) 0.09407(9) 0.9269(2) 0.0654(7) Uani 1 1 d . . . H1A H -0.0566 0.1174 0.9679 0.078 Uiso 1 1 calc R . . H1B H -0.0638 0.0668 0.9142 0.078 Uiso 1 1 calc R . . C3 C 0.2615(3) 0.01384(9) 1.0364(2) 0.0623(7) Uani 1 1 d . . . C2 C 0.1136(3) 0.07966(9) 1.0021(2) 0.0678(7) Uani 1 1 d . . . H2A H 0.1837 0.1035 0.9992 0.081 Uiso 1 1 calc R . . H2B H 0.0875 0.0770 1.0813 0.081 Uiso 1 1 calc R . . C8 C 0.3095(3) -0.02876(10) 0.9963(2) 0.0702(7) Uani 1 1 d . . . C4 C 0.3097(3) 0.03212(11) 1.1411(2) 0.0779(8) Uani 1 1 d . . . H4 H 0.2792 0.0612 1.1661 0.093 Uiso 1 1 calc R . . C6 C 0.4505(3) -0.03528(14) 1.1727(3) 0.0961(10) Uani 1 1 d . . . H6 H 0.5141 -0.0520 1.2183 0.115 Uiso 1 1 calc R . . C9 C 0.2603(3) -0.04756(10) 0.8800(3) 0.0935(9) Uani 1 1 d . . . H9A H 0.2971 -0.0785 0.8691 0.140 Uiso 1 1 calc R . . H9B H 0.2893 -0.0270 0.8205 0.140 Uiso 1 1 calc R . . H9C H 0.1633 -0.0492 0.8764 0.140 Uiso 1 1 calc R . . C7 C 0.4019(3) -0.05279(11) 1.0673(3) 0.0859(9) Uani 1 1 d . . . H7 H 0.4328 -0.0820 1.0434 0.103 Uiso 1 1 calc R . . C5 C 0.4030(3) 0.00688(14) 1.2079(3) 0.0946(10) Uani 1 1 d . . . H5 H 0.4342 0.0190 1.2788 0.114 Uiso 1 1 calc R . . O1 O 0.16490(18) 0.03563(6) 0.96495(14) 0.0694(5) Uani 1 1 d . . . C10 C 0.1019(2) 0.08108(9) 0.7363(2) 0.0642(7) Uani 1 1 d . . . H10A H 0.1176 0.0969 0.6641 0.077 Uiso 1 1 calc R . . H10B H 0.1897 0.0749 0.7744 0.077 Uiso 1 1 calc R . . C12 C -0.1489(3) 0.00221(12) 0.5926(2) 0.0689(7) Uani 1 1 d . . . C13 C -0.1103(3) -0.04282(12) 0.6194(2) 0.0770(8) Uani 1 1 d . . . H13 H -0.0327 -0.0484 0.6662 0.092 Uiso 1 1 calc R . . C11 C 0.0351(3) 0.03469(9) 0.7089(2) 0.0680(7) Uani 1 1 d . . . H11A H 0.0982 0.0140 0.6723 0.082 Uiso 1 1 calc R . . H11B H 0.0088 0.0198 0.7796 0.082 Uiso 1 1 calc R . . C17 C -0.2628(3) 0.01159(13) 0.5193(2) 0.0783(8) Uani 1 1 d . . . C16 C -0.3358(3) -0.02714(16) 0.4777(3) 0.0928(10) Uani 1 1 d . . . H16 H -0.4117 -0.0220 0.4286 0.111 Uiso 1 1 calc R . . C14 C -0.1879(4) -0.08036(12) 0.5763(3) 0.0958(10) Uani 1 1 d . . . H14 H -0.1629 -0.1110 0.5957 0.115 Uiso 1 1 calc R . . C15 C -0.3007(4) -0.07259(16) 0.5058(3) 0.1021(11) Uani 1 1 d . . . H15 H -0.3527 -0.0977 0.4774 0.122 Uiso 1 1 calc R . . C18 C -0.3047(3) 0.06083(12) 0.4904(3) 0.1046(10) Uani 1 1 d . . . H18A H -0.3820 0.0603 0.4370 0.157 Uiso 1 1 calc R . . H18B H -0.2314 0.0770 0.4561 0.157 Uiso 1 1 calc R . . H18C H -0.3276 0.0769 0.5595 0.157 Uiso 1 1 calc R . . O2 O -0.08156(18) 0.04190(6) 0.63372(15) 0.0714(5) Uani 1 1 d . . . C21 C 0.0065(3) 0.23274(11) 0.6286(3) 0.0768(8) Uani 1 1 d . . . C26 C 0.1009(3) 0.25875(12) 0.5717(2) 0.0798(8) Uani 1 1 d . . . C20 C -0.0889(3) 0.15400(10) 0.6356(2) 0.0823(8) Uani 1 1 d . . . H20A H -0.0798 0.1278 0.5830 0.099 Uiso 1 1 calc R . . H20B H -0.1712 0.1708 0.6122 0.099 Uiso 1 1 calc R . . C19 C -0.1019(2) 0.13499(9) 0.7569(2) 0.0699(7) Uani 1 1 d . . . H19A H -0.1313 0.1604 0.8058 0.084 Uiso 1 1 calc R . . H19B H -0.1717 0.1110 0.7548 0.084 Uiso 1 1 calc R . . C22 C -0.0981(3) 0.25439(13) 0.6828(3) 0.0999(10) Uani 1 1 d . . . H22 H -0.1620 0.2362 0.7185 0.120 Uiso 1 1 calc R . . C27 C 0.2089(3) 0.23537(12) 0.5097(3) 0.1009(10) Uani 1 1 d . . . H27A H 0.2587 0.2146 0.5614 0.151 Uiso 1 1 calc R . . H27B H 0.2690 0.2587 0.4812 0.151 Uiso 1 1 calc R . . H27C H 0.1694 0.2176 0.4461 0.151 Uiso 1 1 calc R . . C25 C 0.0869(4) 0.30760(14) 0.5746(3) 0.1055(11) Uani 1 1 d . . . H25 H 0.1488 0.3261 0.5373 0.127 Uiso 1 1 calc R . . C23 C -0.1082(4) 0.30232(14) 0.6843(3) 0.1150(12) Uani 1 1 d . . . H23 H -0.1781 0.3168 0.7216 0.138 Uiso 1 1 calc R . . C24 C -0.0142(5) 0.32910(14) 0.6301(4) 0.1219(13) Uani 1 1 d . . . H24 H -0.0197 0.3618 0.6314 0.146 Uiso 1 1 calc R . . O3 O 0.02349(19) 0.18472(8) 0.62619(19) 0.0985(7) Uani 1 1 d . . . C29 C 0.2279(2) 0.24649(9) 0.8790(2) 0.0605(7) Uani 1 1 d . . . C33 C 0.4126(2) 0.21328(9) 0.7833(2) 0.0564(6) Uani 1 1 d . . . C28 C 0.2917(2) 0.20373(10) 0.8432(2) 0.0600(7) Uani 1 1 d . . . C32 C 0.4601(3) 0.25661(10) 0.7592(2) 0.0627(7) Uani 1 1 d . . . H32 H 0.5396 0.2601 0.7204 0.075 Uiso 1 1 calc R . . C30 C 0.2742(3) 0.29066(9) 0.8543(2) 0.0636(7) Uani 1 1 d . . . H30 H 0.2284 0.3172 0.8789 0.076 Uiso 1 1 calc R . . C31 C 0.3887(3) 0.29561(9) 0.7930(2) 0.0630(7) Uani 1 1 d . . . O4 O 0.25341(17) 0.16294(6) 0.86448(16) 0.0795(6) Uani 1 1 d . . . O5 O 0.0383(2) 0.20863(9) 0.94034(19) 0.1065(8) Uani 1 1 d . . . O9 O 0.6138(2) 0.17455(8) 0.75834(19) 0.1038(7) Uani 1 1 d . . . O10 O 0.4313(2) 0.14014(8) 0.6989(2) 0.1172(8) Uani 1 1 d . . . O6 O 0.0825(2) 0.27785(9) 1.0066(2) 0.1174(8) Uani 1 1 d . . . O7 O 0.3720(3) 0.37632(8) 0.7967(2) 0.1257(9) Uani 1 1 d . . . O8 O 0.5362(3) 0.34561(8) 0.7076(2) 0.1311(10) Uani 1 1 d . . . N4 N 0.4913(3) 0.17284(9) 0.7450(2) 0.0764(7) Uani 1 1 d . . . N2 N 0.1087(3) 0.24412(11) 0.9462(2) 0.0829(7) Uani 1 1 d . . . N3 N 0.4344(3) 0.34216(10) 0.7630(2) 0.0925(8) Uani 1 1 d . . . H1N H 0.086(2) 0.1405(9) 0.829(2) 0.079(8) 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 N1 0.0510(13) 0.0616(14) 0.0652(14) 0.0023(11) 0.0145(11) -0.0027(11) C1 0.0722(18) 0.0625(17) 0.0640(17) 0.0061(13) 0.0291(14) 0.0012(14) C3 0.0652(17) 0.0643(18) 0.0590(18) 0.0081(15) 0.0183(14) -0.0040(14) C2 0.086(2) 0.0632(18) 0.0554(16) -0.0001(13) 0.0161(15) 0.0073(15) C8 0.0708(19) 0.0649(19) 0.076(2) 0.0056(16) 0.0135(16) -0.0054(15) C4 0.087(2) 0.092(2) 0.0558(18) -0.0018(17) 0.0153(16) 0.0050(17) C6 0.097(3) 0.111(3) 0.081(2) 0.025(2) 0.005(2) 0.013(2) C9 0.099(2) 0.077(2) 0.104(2) -0.0234(18) 0.0034(19) 0.0092(17) C7 0.082(2) 0.074(2) 0.103(3) 0.010(2) 0.018(2) 0.0042(17) C5 0.100(3) 0.126(3) 0.0575(19) 0.009(2) 0.0075(18) 0.008(2) O1 0.0833(13) 0.0645(12) 0.0609(11) -0.0062(9) 0.0093(10) 0.0091(10) C10 0.0552(15) 0.0753(18) 0.0638(17) -0.0022(14) 0.0202(13) -0.0018(14) C12 0.0651(19) 0.087(2) 0.0564(17) -0.0128(16) 0.0179(15) -0.0091(18) C13 0.078(2) 0.082(2) 0.0720(19) -0.0203(17) 0.0147(15) -0.0052(18) C11 0.0651(18) 0.0756(19) 0.0640(17) -0.0067(14) 0.0097(14) 0.0034(15) C17 0.065(2) 0.115(3) 0.0550(17) -0.0092(18) 0.0104(15) -0.0164(19) C16 0.072(2) 0.142(3) 0.066(2) -0.023(2) 0.0122(16) -0.012(2) C14 0.103(3) 0.092(2) 0.094(2) -0.030(2) 0.031(2) -0.015(2) C15 0.087(3) 0.132(3) 0.089(3) -0.047(2) 0.019(2) -0.028(2) C18 0.085(2) 0.132(3) 0.096(2) 0.022(2) -0.0086(18) -0.009(2) O2 0.0638(12) 0.0815(13) 0.0687(12) -0.0026(10) 0.0016(10) -0.0035(10) C21 0.079(2) 0.075(2) 0.077(2) 0.0169(16) 0.0098(17) 0.0040(17) C26 0.071(2) 0.105(3) 0.0623(18) 0.0131(17) 0.0023(15) -0.0136(19) C20 0.076(2) 0.081(2) 0.091(2) 0.0171(17) 0.0105(16) -0.0035(17) C19 0.0575(17) 0.0715(18) 0.082(2) 0.0083(15) 0.0153(14) 0.0027(14) C22 0.096(2) 0.103(3) 0.103(3) 0.025(2) 0.023(2) 0.005(2) C27 0.078(2) 0.144(3) 0.081(2) 0.015(2) 0.0109(18) -0.012(2) C25 0.119(3) 0.088(3) 0.110(3) 0.022(2) 0.006(2) -0.023(2) C23 0.126(3) 0.091(3) 0.130(3) 0.008(2) 0.031(3) 0.012(2) C24 0.143(3) 0.087(3) 0.137(3) 0.010(2) 0.020(3) -0.007(3) O3 0.0772(14) 0.0876(16) 0.1328(19) 0.0316(13) 0.0249(12) 0.0002(12) C29 0.0572(16) 0.0716(19) 0.0533(15) -0.0037(13) 0.0096(12) -0.0034(14) C33 0.0565(15) 0.0583(17) 0.0545(15) -0.0016(12) 0.0033(12) 0.0004(13) C28 0.0599(16) 0.0620(19) 0.0579(16) 0.0031(14) -0.0002(13) -0.0063(14) C32 0.0650(17) 0.0706(19) 0.0536(15) -0.0014(14) 0.0143(13) -0.0099(15) C30 0.0704(18) 0.0651(19) 0.0552(16) -0.0070(13) 0.0034(14) 0.0055(14) C31 0.0773(18) 0.0563(18) 0.0558(16) 0.0040(13) 0.0069(14) -0.0092(15) O4 0.0738(12) 0.0637(13) 0.1014(15) 0.0087(10) 0.0079(10) -0.0132(10) O5 0.0860(15) 0.1172(19) 0.1200(19) -0.0077(14) 0.0417(13) -0.0231(14) O9 0.0733(16) 0.1074(17) 0.1321(19) -0.0065(13) 0.0179(14) 0.0158(13) O10 0.1096(18) 0.0860(16) 0.156(2) -0.0467(16) 0.0017(15) 0.0040(14) O6 0.1183(19) 0.1199(19) 0.1192(19) -0.0302(15) 0.0590(15) -0.0012(15) O7 0.156(2) 0.0579(15) 0.165(2) 0.0069(15) 0.0281(18) 0.0040(15) O8 0.175(2) 0.0955(17) 0.129(2) 0.0138(14) 0.0689(19) -0.0433(16) N4 0.0741(18) 0.0758(19) 0.0802(17) -0.0014(14) 0.0114(14) 0.0047(16) N2 0.0761(17) 0.090(2) 0.0842(18) -0.0055(15) 0.0224(14) -0.0079(16) N3 0.123(2) 0.066(2) 0.090(2) 0.0068(15) 0.0175(17) -0.0185(17) _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 N1 C10 1.501(3) . ? N1 C19 1.505(3) . ? N1 C1 1.513(3) . ? C1 C2 1.489(3) . ? C3 O1 1.379(3) . ? C3 C4 1.383(4) . ? C3 C8 1.388(3) . ? C2 O1 1.424(3) . ? C8 C7 1.380(4) . ? C8 C9 1.509(4) . ? C4 C5 1.376(4) . ? C6 C5 1.356(4) . ? C6 C7 1.384(4) . ? C10 C11 1.500(3) . ? C12 C13 1.366(4) . ? C12 O2 1.381(3) . ? C12 C17 1.403(4) . ? C13 C14 1.392(4) . ? C11 O2 1.426(3) . ? C17 C16 1.388(4) . ? C17 C18 1.491(4) . ? C16 C15 1.371(4) . ? C14 C15 1.367(4) . ? C21 O3 1.374(3) . ? C21 C22 1.382(4) . ? C21 C26 1.383(4) . ? C26 C25 1.394(4) . ? C26 C27 1.476(4) . ? C20 O3 1.422(3) . ? C20 C19 1.519(3) . ? C22 C23 1.364(4) . ? C25 C24 1.361(5) . ? C23 C24 1.378(5) . ? C29 C30 1.370(3) . ? C29 C28 1.439(3) . ? C29 N2 1.448(3) . ? C33 C32 1.351(3) . ? C33 C28 1.438(3) . ? C33 N4 1.468(3) . ? C28 O4 1.247(3) . ? C32 C31 1.381(3) . ? C30 C31 1.374(3) . ? C31 N3 1.445(3) . ? O5 N2 1.225(3) . ? O9 N4 1.215(3) . ? O10 N4 1.211(3) . ? O6 N2 1.222(3) . ? O7 N3 1.224(3) . ? O8 N3 1.226(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 C10 N1 C19 116.1(2) . . ? C10 N1 C1 114.06(19) . . ? C19 N1 C1 107.92(18) . . ? C2 C1 N1 115.5(2) . . ? O1 C3 C4 123.9(2) . . ? O1 C3 C8 115.3(2) . . ? C4 C3 C8 120.8(3) . . ? O1 C2 C1 110.4(2) . . ? C7 C8 C3 117.3(3) . . ? C7 C8 C9 122.2(3) . . ? C3 C8 C9 120.5(3) . . ? C5 C4 C3 119.4(3) . . ? C5 C6 C7 118.2(3) . . ? C8 C7 C6 122.7(3) . . ? C6 C5 C4 121.5(3) . . ? C3 O1 C2 117.28(19) . . ? C11 C10 N1 116.44(19) . . ? C13 C12 O2 124.1(3) . . ? C13 C12 C17 121.5(3) . . ? O2 C12 C17 114.4(3) . . ? C12 C13 C14 119.5(3) . . ? O2 C11 C10 109.7(2) . . ? C16 C17 C12 116.6(3) . . ? C16 C17 C18 122.1(3) . . ? C12 C17 C18 121.3(3) . . ? C15 C16 C17 122.8(3) . . ? C15 C14 C13 120.7(3) . . ? C16 C15 C14 118.9(3) . . ? C12 O2 C11 117.1(2) . . ? O3 C21 C22 123.1(3) . . ? O3 C21 C26 115.7(3) . . ? C22 C21 C26 121.2(3) . . ? C21 C26 C25 116.7(3) . . ? C21 C26 C27 121.0(3) . . ? C25 C26 C27 122.3(3) . . ? O3 C20 C19 113.1(2) . . ? N1 C19 C20 114.5(2) . . ? C23 C22 C21 120.4(3) . . ? C24 C25 C26 122.2(3) . . ? C22 C23 C24 119.5(4) . . ? C25 C24 C23 119.9(4) . . ? C21 O3 C20 120.7(2) . . ? C30 C29 C28 123.7(2) . . ? C30 C29 N2 116.4(2) . . ? C28 C29 N2 119.8(2) . . ? C32 C33 C28 125.3(2) . . ? C32 C33 N4 117.0(2) . . ? C28 C33 N4 117.7(2) . . ? O4 C28 C33 122.6(2) . . ? O4 C28 C29 125.7(2) . . ? C33 C28 C29 111.6(2) . . ? C33 C32 C31 118.9(2) . . ? C29 C30 C31 119.7(2) . . ? C30 C31 C32 120.8(2) . . ? C30 C31 N3 119.6(3) . . ? C32 C31 N3 119.6(3) . . ? O10 N4 O9 123.4(3) . . ? O10 N4 C33 118.5(2) . . ? O9 N4 C33 118.1(3) . . ? O6 N2 O5 122.7(3) . . ? O6 N2 C29 118.3(3) . . ? O5 N2 C29 119.0(3) . . ? O7 N3 O8 123.0(3) . . ? O7 N3 C31 118.6(3) . . ? O8 N3 C31 118.4(3) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 28.48 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.256 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.056 data_p-CresolPMA _database_code_depnum_ccdc_archive 'CCDC 766472' #TrackingRef 'all cif.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H39 N O11' _chemical_formula_weight 673.69 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 Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.4682(13) _cell_length_b 13.6433(13) _cell_length_c 20.291(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.935(3) _cell_angle_gamma 90.00 _cell_volume 3602.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.972 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details 'SADAS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 16599 _diffrn_reflns_av_R_equivalents 0.1090 _diffrn_reflns_av_sigmaI/netI 0.1040 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 26.80 _reflns_number_total 7600 _reflns_number_gt 7498 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0676P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5739 _refine_ls_number_parameters 453 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0982 _refine_ls_R_factor_gt 0.0615 _refine_ls_wR_factor_ref 0.1611 _refine_ls_wR_factor_gt 0.1328 _refine_ls_goodness_of_fit_ref 0.937 _refine_ls_restrained_S_all 0.937 _refine_ls_shift/su_max 0.005 _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 N1 N 0.70825(19) 0.93142(19) 0.33714(15) 0.0550(8) Uani 1 1 d . . . C1 C 0.8158(2) 0.9539(2) 0.33407(18) 0.0626(10) Uani 1 1 d . . . H1A H 0.8411 1.0076 0.3651 0.075 Uiso 1 1 calc R . . H1B H 0.8133 0.9768 0.2884 0.075 Uiso 1 1 calc R . . C2 C 0.8926(2) 0.8716(2) 0.35092(19) 0.0656(10) Uani 1 1 d . . . H2A H 0.8599 0.8100 0.3342 0.079 Uiso 1 1 calc R . . H2B H 0.9482 0.8831 0.3295 0.079 Uiso 1 1 calc R . . C3 C 1.0233(3) 0.8180(3) 0.4484(2) 0.0663(10) Uani 1 1 d . . . C5 C 1.1659(3) 0.7955(3) 0.5447(2) 0.0859(12) Uani 1 1 d . . . H5 H 1.1990 0.8107 0.5897 0.103 Uiso 1 1 calc R . . C4 C 1.0735(3) 0.8398(3) 0.5143(2) 0.0823(12) Uani 1 1 d . . . H4 H 1.0452 0.8848 0.5387 0.099 Uiso 1 1 calc R . . C8 C 1.0637(3) 0.7500(3) 0.4131(2) 0.0768(11) Uani 1 1 d . . . H8 H 1.0291 0.7334 0.3686 0.092 Uiso 1 1 calc R . . C6 C 1.2097(3) 0.7297(3) 0.5100(2) 0.0802(12) Uani 1 1 d . . . C7 C 1.1574(3) 0.7058(3) 0.4444(2) 0.0857(12) Uani 1 1 d . . . H7 H 1.1850 0.6595 0.4205 0.103 Uiso 1 1 calc R . . C9 C 1.3150(3) 0.6846(3) 0.5420(2) 0.1262(17) Uani 1 1 d . . . H9A H 1.3468 0.6660 0.5067 0.189 Uiso 1 1 calc R . . H9B H 1.3068 0.6277 0.5680 0.189 Uiso 1 1 calc R . . H9C H 1.3574 0.7317 0.5715 0.189 Uiso 1 1 calc R . . O1 O 0.93153(17) 0.86777(17) 0.42255(13) 0.0797(8) Uani 1 1 d . . . C11 C 0.5976(3) 0.8906(3) 0.4158(2) 0.0771(11) Uani 1 1 d . . . H11A H 0.5607 0.8378 0.3878 0.093 Uiso 1 1 calc R . . H11B H 0.5991 0.8778 0.4630 0.093 Uiso 1 1 calc R . . C12 C 0.4516(3) 0.9975(3) 0.40100(18) 0.0675(10) Uani 1 1 d . . . C10 C 0.7059(2) 0.8990(2) 0.4071(2) 0.0734(11) Uani 1 1 d . . . H10A H 0.7442 0.9455 0.4402 0.088 Uiso 1 1 calc R . . H10B H 0.7396 0.8359 0.4165 0.088 Uiso 1 1 calc R . . C16 C 0.3151(3) 1.1127(3) 0.3883(2) 0.0871(13) Uani 1 1 d . . . H16 H 0.2899 1.1756 0.3772 0.104 Uiso 1 1 calc R . . C17 C 0.4137(3) 1.0905(3) 0.3840(2) 0.0816(12) Uani 1 1 d . . . H17 H 0.4536 1.1377 0.3698 0.098 Uiso 1 1 calc R . . C13 C 0.3912(3) 0.9276(3) 0.42072(19) 0.0808(12) Uani 1 1 d . . . H13 H 0.4161 0.8645 0.4318 0.097 Uiso 1 1 calc R . . C15 C 0.2530(3) 1.0445(3) 0.4086(2) 0.0799(12) Uani 1 1 d . . . C14 C 0.2930(3) 0.9527(3) 0.4239(2) 0.0850(12) Uani 1 1 d . . . H14 H 0.2525 0.9051 0.4370 0.102 Uiso 1 1 calc R . . C18 C 0.1452(3) 1.0707(3) 0.4128(2) 0.1115(15) Uani 1 1 d . . . H18A H 0.0992 1.0691 0.3680 0.167 Uiso 1 1 calc R . . H18B H 0.1455 1.1353 0.4316 0.167 Uiso 1 1 calc R . . H18C H 0.1229 1.0244 0.4416 0.167 Uiso 1 1 calc R . . O2 O 0.55010(19) 0.98154(16) 0.39465(13) 0.0795(8) Uani 1 1 d . . . C20 C 0.6532(3) 0.8881(3) 0.2118(2) 0.0755(11) Uani 1 1 d . . . H20A H 0.5963 0.8572 0.1792 0.091 Uiso 1 1 calc R . . H20B H 0.6473 0.9585 0.2055 0.091 Uiso 1 1 calc R . . C19 C 0.6513(2) 0.8614(2) 0.2832(2) 0.0711(11) Uani 1 1 d . . . H19A H 0.6807 0.7966 0.2935 0.085 Uiso 1 1 calc R . . H19B H 0.5803 0.8582 0.2855 0.085 Uiso 1 1 calc R . . C21 C 0.7678(3) 0.8730(3) 0.1401(3) 0.0781(12) Uani 1 1 d . . . C22 C 0.8661(4) 0.8511(3) 0.1374(3) 0.1022(15) Uani 1 1 d . . . H22 H 0.9136 0.8264 0.1754 0.123 Uiso 1 1 calc R . . C26 C 0.6986(4) 0.9067(3) 0.0835(3) 0.1073(15) Uani 1 1 d . . . H25 H 0.6318 0.9213 0.0849 0.129 Uiso 1 1 calc R . . C24 C 0.8273(5) 0.9013(4) 0.0193(3) 0.1200(17) Uani 1 1 d . . . C23 C 0.8933(4) 0.8664(4) 0.0771(3) 0.1195(18) Uani 1 1 d . . . H23 H 0.9603 0.8521 0.0759 0.143 Uiso 1 1 calc R . . C27 C 0.8610(5) 0.9210(4) -0.0464(3) 0.185(3) Uani 1 1 d . . . H26A H 0.9321 0.9038 -0.0394 0.277 Uiso 1 1 calc R . . H26B H 0.8519 0.9892 -0.0580 0.277 Uiso 1 1 calc R . . H26C H 0.8200 0.8823 -0.0830 0.277 Uiso 1 1 calc R . . O3 O 0.74719(19) 0.85512(17) 0.20185(15) 0.0776(8) Uani 1 1 d . . . C32 C 0.3072(2) 0.77790(19) 0.24249(15) 0.0413(8) Uani 1 1 d . . . C31 C 0.2076(2) 0.77400(19) 0.24900(15) 0.0438(8) Uani 1 1 d . . . C28 C 0.2934(2) 0.95530(19) 0.22681(16) 0.0447(8) Uani 1 1 d . . . C33 C 0.3475(2) 0.8678(2) 0.23142(16) 0.0499(9) Uani 1 1 d . . . H28 H 0.4144 0.8698 0.2268 0.060 Uiso 1 1 calc R . . C29 C 0.1920(2) 0.9513(2) 0.23433(16) 0.0460(8) Uani 1 1 d . . . C30 C 0.1522(2) 0.8600(2) 0.24477(16) 0.0522(9) Uani 1 1 d . . . H31 H 0.0852 0.8569 0.2491 0.063 Uiso 1 1 calc R . . C34 C 0.3528(3) 1.0445(2) 0.21552(18) 0.0582(10) Uani 1 1 d . . . C35 C 0.1166(3) 1.0348(2) 0.23327(18) 0.0585(10) Uani 1 1 d . . . C37 C 0.3707(2) 0.6875(2) 0.24188(19) 0.0512(9) Uani 1 1 d . . . C36 C 0.1621(2) 0.6789(2) 0.26347(18) 0.0528(9) Uani 1 1 d . . . O7 O 0.34426(16) 0.62490(15) 0.19938(12) 0.0666(7) Uani 1 1 d . . . O4 O 0.31267(17) 1.12869(16) 0.20919(14) 0.0836(8) Uani 1 1 d . . . O11 O 0.14124(16) 1.12349(15) 0.22236(15) 0.0812(8) Uani 1 1 d . . . H11 H 0.1989 1.1241 0.2159 0.122 Uiso 1 1 calc R . . O5 O 0.44260(17) 1.03179(14) 0.21200(14) 0.0803(8) Uani 1 1 d . . . O10 O 0.03300(17) 1.01695(14) 0.24330(14) 0.0798(8) Uani 1 1 d . . . O9 O 0.06195(15) 0.67545(18) 0.24061(14) 0.0848(9) Uani 1 1 d . . . H9 H 0.0465 0.6677 0.1991 0.127 Uiso 1 1 calc R . . O6 O 0.45621(16) 0.68760(14) 0.28948(14) 0.0843(9) Uani 1 1 d . . . H6 H 0.4877 0.6367 0.2875 0.127 Uiso 1 1 calc R . . O8 O 0.21280(16) 0.61301(15) 0.29418(12) 0.0691(7) Uani 1 1 d . . . C25 C 0.7287(5) 0.9192(4) 0.0235(3) 0.1318(19) Uani 1 1 d . . . H37 H 0.6802 0.9404 -0.0153 0.158 Uiso 1 1 calc R . . H1N H 0.672(2) 0.997(2) 0.3342(15) 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 N1 0.0464(18) 0.0358(17) 0.082(2) 0.0037(15) 0.0144(15) 0.0026(14) C1 0.049(2) 0.043(2) 0.093(3) -0.0034(17) 0.0141(19) -0.0064(18) C2 0.050(2) 0.065(2) 0.080(3) -0.0009(19) 0.013(2) 0.0056(18) C3 0.050(2) 0.069(3) 0.080(3) 0.000(2) 0.017(2) 0.012(2) C5 0.076(3) 0.098(3) 0.076(3) -0.009(2) 0.006(2) 0.016(3) C4 0.068(3) 0.092(3) 0.083(4) -0.012(2) 0.012(2) 0.014(2) C8 0.068(3) 0.082(3) 0.079(3) -0.004(2) 0.016(2) 0.018(2) C6 0.066(3) 0.079(3) 0.091(4) 0.008(2) 0.012(2) 0.015(2) C7 0.081(3) 0.082(3) 0.093(4) -0.001(2) 0.020(3) 0.027(2) C9 0.097(3) 0.145(4) 0.120(4) 0.007(3) -0.002(3) 0.056(3) O1 0.0578(15) 0.1000(19) 0.077(2) -0.0056(14) 0.0102(13) 0.0221(14) C11 0.069(3) 0.065(3) 0.101(3) 0.018(2) 0.029(2) 0.008(2) C12 0.059(3) 0.067(3) 0.083(3) 0.003(2) 0.031(2) 0.002(2) C10 0.060(3) 0.067(3) 0.093(3) 0.009(2) 0.018(2) 0.0098(19) C16 0.079(3) 0.073(3) 0.111(4) 0.000(2) 0.029(3) 0.021(3) C17 0.085(3) 0.054(3) 0.112(4) 0.007(2) 0.036(2) 0.006(2) C13 0.076(3) 0.074(3) 0.105(3) 0.016(2) 0.045(2) 0.010(2) C15 0.069(3) 0.092(3) 0.084(3) -0.007(2) 0.028(2) 0.005(3) C14 0.074(3) 0.084(3) 0.105(4) 0.007(2) 0.038(2) 0.002(3) C18 0.069(3) 0.150(4) 0.120(4) 0.002(3) 0.035(3) 0.029(3) O2 0.0740(18) 0.0585(17) 0.116(2) 0.0166(14) 0.0432(15) 0.0113(14) C20 0.057(3) 0.070(3) 0.095(4) -0.019(2) 0.011(2) 0.007(2) C19 0.054(2) 0.045(2) 0.111(4) -0.013(2) 0.016(2) -0.0044(17) C21 0.075(3) 0.063(3) 0.093(4) -0.014(2) 0.017(3) 0.010(2) C22 0.072(3) 0.131(4) 0.106(5) -0.019(3) 0.025(3) 0.011(3) C26 0.102(4) 0.117(4) 0.107(5) 0.014(3) 0.033(4) 0.038(3) C24 0.130(5) 0.115(4) 0.127(6) 0.001(3) 0.054(4) 0.028(4) C23 0.094(4) 0.144(5) 0.126(6) -0.024(4) 0.037(4) 0.015(3) C27 0.212(6) 0.223(7) 0.152(6) 0.018(5) 0.105(5) 0.053(5) O3 0.0630(18) 0.0725(18) 0.097(2) -0.0029(15) 0.0193(15) 0.0175(13) C32 0.0262(17) 0.0251(18) 0.077(2) -0.0019(14) 0.0214(15) 0.0000(14) C31 0.0336(18) 0.0215(18) 0.081(2) -0.0014(14) 0.0233(15) -0.0024(15) C28 0.0301(18) 0.0227(18) 0.082(3) 0.0010(14) 0.0156(16) -0.0032(15) C33 0.0233(16) 0.0332(19) 0.095(3) -0.0054(16) 0.0193(16) -0.0009(15) C29 0.0334(18) 0.0258(18) 0.080(3) -0.0031(15) 0.0168(16) 0.0007(15) C30 0.0290(16) 0.036(2) 0.095(3) -0.0056(16) 0.0222(16) -0.0004(16) C34 0.044(2) 0.035(2) 0.097(3) -0.0025(18) 0.0205(19) -0.0077(19) C35 0.047(2) 0.028(2) 0.101(3) 0.0000(18) 0.0201(19) 0.0012(18) C37 0.0353(19) 0.025(2) 0.099(3) -0.0025(18) 0.0267(19) -0.0027(16) C36 0.043(2) 0.031(2) 0.092(3) -0.0029(17) 0.0310(19) 0.0021(17) O7 0.0623(15) 0.0312(13) 0.106(2) -0.0130(12) 0.0216(13) 0.0048(11) O4 0.0625(15) 0.0288(14) 0.166(3) 0.0118(14) 0.0421(16) -0.0024(12) O11 0.0585(15) 0.0332(15) 0.160(3) 0.0119(14) 0.0431(16) 0.0101(12) O5 0.0425(14) 0.0371(14) 0.171(3) 0.0036(13) 0.0444(15) -0.0096(11) O10 0.0407(14) 0.0458(15) 0.164(3) -0.0018(14) 0.0463(15) 0.0066(12) O9 0.0395(14) 0.0559(16) 0.157(3) 0.0127(18) 0.0212(14) -0.0053(12) O6 0.0415(14) 0.0397(14) 0.157(3) -0.0245(14) -0.0003(15) 0.0135(11) O8 0.0615(15) 0.0369(14) 0.112(2) 0.0144(13) 0.0280(14) 0.0007(12) C25 0.134(5) 0.152(5) 0.106(5) 0.017(4) 0.026(4) 0.053(4) _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 N1 C10 1.495(4) . ? N1 C1 1.497(4) . ? N1 C19 1.505(4) . ? C1 C2 1.505(4) . ? C2 O1 1.413(4) . ? C3 C4 1.366(4) . ? C3 C8 1.368(4) . ? C3 O1 1.389(4) . ? C5 C6 1.364(5) . ? C5 C4 1.378(5) . ? C8 C7 1.395(4) . ? C6 C7 1.376(5) . ? C6 C9 1.529(5) . ? C11 O2 1.411(3) . ? C11 C10 1.518(4) . ? C12 C13 1.377(5) . ? C12 C17 1.379(4) . ? C12 O2 1.383(4) . ? C16 C15 1.382(5) . ? C16 C17 1.387(5) . ? C13 C14 1.383(4) . ? C15 C14 1.368(5) . ? C15 C18 1.519(5) . ? C20 O3 1.406(4) . ? C20 C19 1.501(4) . ? C21 C26 1.360(5) . ? C21 C22 1.372(5) . ? C21 O3 1.373(5) . ? C22 C23 1.378(6) . ? C26 C25 1.388(6) . ? C24 C23 1.362(6) . ? C24 C25 1.374(7) . ? C24 C27 1.540(7) . ? C32 C31 1.382(4) . ? C32 C33 1.383(3) . ? C32 C37 1.502(4) . ? C31 C30 1.381(4) . ? C31 C36 1.496(4) . ? C28 C33 1.389(4) . ? C28 C29 1.414(4) . ? C28 C34 1.506(4) . ? C29 C30 1.393(4) . ? C29 C35 1.523(4) . ? C34 O5 1.241(3) . ? C34 O4 1.262(3) . ? C35 O10 1.220(3) . ? C35 O11 1.288(3) . ? C37 O7 1.201(3) . ? C37 O6 1.299(3) . ? C36 O8 1.201(3) . ? C36 O9 1.310(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 C10 N1 C1 110.9(2) . . ? C10 N1 C19 111.8(3) . . ? C1 N1 C19 114.7(3) . . ? N1 C1 C2 117.0(3) . . ? O1 C2 C1 108.2(3) . . ? C4 C3 C8 119.8(3) . . ? C4 C3 O1 115.5(4) . . ? C8 C3 O1 124.7(4) . . ? C6 C5 C4 121.2(4) . . ? C3 C4 C5 120.3(4) . . ? C3 C8 C7 119.3(4) . . ? C5 C6 C7 118.3(4) . . ? C5 C6 C9 121.5(4) . . ? C7 C6 C9 120.2(4) . . ? C6 C7 C8 121.1(4) . . ? C3 O1 C2 117.7(3) . . ? O2 C11 C10 105.8(3) . . ? C13 C12 C17 120.2(4) . . ? C13 C12 O2 124.8(3) . . ? C17 C12 O2 115.0(4) . . ? N1 C10 C11 112.9(3) . . ? C15 C16 C17 122.4(4) . . ? C12 C17 C16 118.9(4) . . ? C12 C13 C14 119.0(4) . . ? C14 C15 C16 116.7(4) . . ? C14 C15 C18 122.0(4) . . ? C16 C15 C18 121.3(4) . . ? C15 C14 C13 122.8(4) . . ? C12 O2 C11 118.7(3) . . ? O3 C20 C19 107.6(3) . . ? C20 C19 N1 114.5(3) . . ? C26 C21 C22 119.8(5) . . ? C26 C21 O3 125.1(5) . . ? C22 C21 O3 115.0(4) . . ? C21 C22 C23 118.8(5) . . ? C21 C26 C25 119.4(5) . . ? C23 C24 C25 115.8(5) . . ? C23 C24 C27 122.4(6) . . ? C25 C24 C27 121.8(6) . . ? C24 C23 C22 123.6(5) . . ? C21 O3 C20 118.4(3) . . ? C31 C32 C33 118.7(2) . . ? C31 C32 C37 122.5(2) . . ? C33 C32 C37 118.6(2) . . ? C30 C31 C32 118.9(2) . . ? C30 C31 C36 120.5(3) . . ? C32 C31 C36 120.6(3) . . ? C33 C28 C29 117.6(2) . . ? C33 C28 C34 114.5(3) . . ? C29 C28 C34 127.9(3) . . ? C32 C33 C28 123.5(3) . . ? C30 C29 C28 118.1(2) . . ? C30 C29 C35 112.9(3) . . ? C28 C29 C35 128.9(3) . . ? C31 C30 C29 123.1(3) . . ? O5 C34 O4 121.3(3) . . ? O5 C34 C28 117.4(3) . . ? O4 C34 C28 121.3(3) . . ? O10 C35 O11 120.4(3) . . ? O10 C35 C29 119.3(3) . . ? O11 C35 C29 120.3(3) . . ? O7 C37 O6 125.2(3) . . ? O7 C37 C32 121.7(3) . . ? O6 C37 C32 113.0(3) . . ? O8 C36 O9 123.5(3) . . ? O8 C36 C31 123.0(3) . . ? O9 C36 C31 113.5(3) . . ? C24 C25 C26 122.5(5) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.80 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.199 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.041