# 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 'Grepioni, Fabrizia' _publ_contact_author_email fabrizia.grepioni@unibo.it _publ_section_title ; Remarkable reversal of melting point alternation by co-crystallization ; _publ_author_name F.Grepioni # Attachment '- 1C10.CIF' data_1.C10 _database_code_depnum_ccdc_archive 'CCDC 763737' #TrackingRef '- 1C10.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H28 N2 O4' _chemical_formula_weight 384.46 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 6.9363(4) _cell_length_b 6.9574(4) _cell_length_c 12.0029(8) _cell_angle_alpha 77.230(5) _cell_angle_beta 73.739(6) _cell_angle_gamma 71.192(6) _cell_volume 520.90(5) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 206 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4579 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0655 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 29.09 _reflns_number_total 2332 _reflns_number_gt 1038 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0799P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2332 _refine_ls_number_parameters 144 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1432 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1505 _refine_ls_wR_factor_gt 0.1241 _refine_ls_goodness_of_fit_ref 0.862 _refine_ls_restrained_S_all 0.862 _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 0.6712(3) 0.5845(2) 0.31070(15) 0.0697(5) Uani 1 1 d . . . H100 H 0.699(4) 0.700(4) 0.263(2) 0.105 Uiso 1 1 d . . . O2 O 0.4031(3) 0.6677(2) 0.22755(15) 0.0788(6) Uani 1 1 d . . . C2 C 0.4540(4) 0.3674(3) 0.3714(2) 0.0553(6) Uani 1 1 d . . . H2A H 0.4558 0.3721 0.4512 0.097(9) Uiso 1 1 d R . . H2B H 0.5653 0.2487 0.3457 0.107(10) Uiso 1 1 d R . . C4 C 0.5025(4) 0.5566(3) 0.29605(18) 0.0480(6) Uani 1 1 d . . . C9 C 0.2497(4) 0.3354(3) 0.3735(2) 0.0566(7) Uani 1 1 d . . . H9A H 0.1359 0.4490 0.4035 0.119(11) Uiso 1 1 d R . . H9B H 0.2437 0.3334 0.2940 0.090(9) Uiso 1 1 d R . . C11 C 0.2207(4) 0.1364(3) 0.4484(2) 0.0608(7) Uani 1 1 d . . . H11A H 0.2451 0.1328 0.5246 0.107(10) Uiso 1 1 d R . . H11B H 0.3270 0.0235 0.4129 0.106(10) Uiso 1 1 d R . . C14 C 0.0102(4) 0.1027(3) 0.4663(2) 0.0611(7) Uani 1 1 d . . . H14A H -0.0190 0.1162 0.3900 0.113(10) Uiso 1 1 d R . . H14B H -0.0953 0.2097 0.5072 0.146(14) Uiso 1 1 d R . . N1 N 0.7654(3) -0.0797(2) 0.18454(15) 0.0530(5) Uani 1 1 d . . . C1 C 0.9024(3) 0.4810(3) -0.0044(2) 0.0570(6) Uani 1 1 d . . . H1A H 0.9067 0.4858 -0.0864 0.103(10) Uiso 1 1 d R . . H1B H 0.7852 0.5928 0.0247 0.100(9) Uiso 1 1 d R . . C3 C 0.9823(4) 0.1440(3) 0.13478(19) 0.0555(6) Uani 1 1 d . . . H3 H 1.0994 0.1705 0.1443 0.072(7) Uiso 1 1 d R . . C5 C 0.6906(4) 0.2300(3) 0.0524(2) 0.0591(7) Uani 1 1 d . . . H5 H 0.6045 0.3163 0.0040 0.074(7) Uiso 1 1 d R . . C7 C 0.8605(3) 0.2819(3) 0.06246(17) 0.0458(6) Uani 1 1 d . . . C13 C 0.6478(4) 0.0517(3) 0.1153(2) 0.0587(7) Uani 1 1 d . . . H13 H 0.5308 0.0220 0.1083 0.071(8) Uiso 1 1 d R . . C20 C 0.9298(4) -0.0333(3) 0.19289(19) 0.0576(7) Uani 1 1 d . . . H20 H 1.0150 -0.1254 0.2401 0.070(7) Uiso 1 1 d 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 0.0745(12) 0.0611(10) 0.0866(12) 0.0288(8) -0.0338(10) -0.0492(9) O2 0.0742(13) 0.0705(11) 0.0970(12) 0.0358(9) -0.0403(10) -0.0411(9) C2 0.0624(17) 0.0495(14) 0.0609(15) 0.0133(10) -0.0166(12) -0.0365(12) C4 0.0498(15) 0.0437(12) 0.0532(13) 0.0032(10) -0.0103(12) -0.0245(11) C9 0.0564(16) 0.0486(13) 0.0677(16) 0.0111(11) -0.0116(12) -0.0334(12) C11 0.0620(17) 0.0538(15) 0.0732(17) 0.0123(12) -0.0160(13) -0.0385(13) C14 0.0631(17) 0.0575(14) 0.0731(17) 0.0152(12) -0.0203(14) -0.0427(14) N1 0.0542(12) 0.0431(11) 0.0620(12) 0.0038(9) -0.0064(10) -0.0272(9) C1 0.0610(17) 0.0444(13) 0.0671(15) 0.0107(10) -0.0135(13) -0.0302(12) C3 0.0542(15) 0.0512(13) 0.0666(15) 0.0071(11) -0.0138(12) -0.0324(11) C5 0.0597(16) 0.0439(13) 0.0780(16) 0.0083(11) -0.0246(13) -0.0239(12) C7 0.0523(14) 0.0337(11) 0.0513(13) 0.0031(9) -0.0073(11) -0.0218(10) C13 0.0538(16) 0.0488(14) 0.0811(18) 0.0000(12) -0.0152(13) -0.0307(12) C20 0.0587(16) 0.0465(13) 0.0681(15) 0.0148(11) -0.0174(13) -0.0278(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.309(2) . ? O1 H100 0.92(3) . ? O2 C4 1.201(2) . ? C2 C9 1.497(3) . ? C2 C4 1.501(3) . ? C2 H2A 0.9699 . ? C2 H2B 0.9699 . ? C9 C11 1.515(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9699 . ? C11 C14 1.502(3) . ? C11 H11A 0.9696 . ? C11 H11B 0.9696 . ? C14 C14 1.508(4) 2_556 ? C14 H14A 0.9698 . ? C14 H14B 0.9697 . ? N1 C20 1.315(3) . ? N1 C13 1.325(3) . ? C1 C1 1.497(4) 2_765 ? C1 C7 1.512(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C3 C20 1.382(3) . ? C3 C7 1.381(3) . ? C3 H3 0.9296 . ? C5 C13 1.376(3) . ? C5 C7 1.381(3) . ? C5 H5 0.9297 . ? C13 H13 0.9288 . ? C20 H20 0.9298 . ? 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 C4 O1 H100 110.6(17) . . ? C9 C2 C4 116.58(19) . . ? C9 C2 H2A 107.8 . . ? C4 C2 H2A 108.1 . . ? C9 C2 H2B 108.4 . . ? C4 C2 H2B 108.4 . . ? H2A C2 H2B 107.3 . . ? O2 C4 O1 123.24(19) . . ? O2 C4 C2 124.6(2) . . ? O1 C4 C2 112.13(19) . . ? C2 C9 C11 112.08(19) . . ? C2 C9 H9A 109.6 . . ? C11 C9 H9A 109.2 . . ? C2 C9 H9B 109.0 . . ? C11 C9 H9B 109.0 . . ? H9A C9 H9B 107.9 . . ? C14 C11 C9 115.7(2) . . ? C14 C11 H11A 108.4 . . ? C9 C11 H11A 108.1 . . ? C14 C11 H11B 108.6 . . ? C9 C11 H11B 108.4 . . ? H11A C11 H11B 107.5 . . ? C11 C14 C14 114.8(3) . 2_556 ? C11 C14 H14A 108.5 . . ? C14 C14 H14A 108.4 2_556 . ? C11 C14 H14B 108.8 . . ? C14 C14 H14B 108.6 2_556 . ? H14A C14 H14B 107.5 . . ? C20 N1 C13 117.11(18) . . ? C1 C1 C7 116.1(2) 2_765 . ? C1 C1 H1A 108.7 2_765 . ? C7 C1 H1A 108.6 . . ? C1 C1 H1B 107.6 2_765 . ? C7 C1 H1B 107.9 . . ? H1A C1 H1B 107.5 . . ? C20 C3 C7 119.8(2) . . ? C20 C3 H3 120.1 . . ? C7 C3 H3 120.1 . . ? C13 C5 C7 119.8(2) . . ? C13 C5 H5 120.2 . . ? C7 C5 H5 119.9 . . ? C5 C7 C3 116.36(18) . . ? C5 C7 C1 119.4(2) . . ? C3 C7 C1 124.3(2) . . ? N1 C13 C5 123.4(2) . . ? N1 C13 H13 118.5 . . ? C5 C13 H13 118.1 . . ? N1 C20 C3 123.4(2) . . ? N1 C20 H20 118.0 . . ? C3 C20 H20 118.6 . . ? _diffrn_measured_fraction_theta_max 0.833 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.211 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.039 # Attachment '- 1C8.CIF' data_1.C8 _database_code_depnum_ccdc_archive 'CCDC 763738' #TrackingRef '- 1C8.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H26 N2 O4' _chemical_formula_weight 358.43 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 P21/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 11.6701(5) _cell_length_b 20.9348(7) _cell_length_c 12.9988(5) _cell_angle_alpha 90.00 _cell_angle_beta 114.656(5) _cell_angle_gamma 90.00 _cell_volume 2886.21(19) _cell_formula_units_Z 6 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13402 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 28.40 _reflns_number_total 6159 _reflns_number_gt 3900 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0758P)^2^+2.2369P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0037(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6159 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1188 _refine_ls_R_factor_gt 0.0793 _refine_ls_wR_factor_ref 0.2062 _refine_ls_wR_factor_gt 0.1883 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 H1O H 0.807(3) 0.2587(18) 0.187(3) 0.088(12) Uiso 1 1 d . . . H4O H 0.693(3) 0.5697(18) 0.305(3) 0.092(12) Uiso 1 1 d . . . H3O H 0.294(3) 0.0882(18) -0.309(3) 0.085(12) Uiso 1 1 d . . . O1 O 0.85514(19) 0.29636(9) 0.20238(16) 0.0520(5) Uani 1 1 d . . . N1 N 0.7240(2) 0.18903(10) 0.14447(18) 0.0423(5) Uani 1 1 d . . . O2 O 0.7874(2) 0.30772(10) 0.33657(18) 0.0728(7) Uani 1 1 d . . . C1 C 0.9243(2) 0.38746(11) 0.3172(2) 0.0379(6) Uani 1 1 d . . . H1A H 0.8903 0.4161 0.2527 0.045 Uiso 1 1 calc R . . H1B H 1.0105 0.3776 0.3303 0.045 Uiso 1 1 calc R . . C2 C 0.8486(2) 0.32657(12) 0.2883(2) 0.0383(6) Uani 1 1 d . . . C3 C 0.9249(2) 0.42160(11) 0.42021(19) 0.0377(6) Uani 1 1 d . . . H3A H 0.9593 0.3931 0.4848 0.045 Uiso 1 1 calc R . . H3B H 0.8386 0.4313 0.4072 0.045 Uiso 1 1 calc R . . C4 C 0.7206(3) 0.15640(12) 0.0556(2) 0.0469(7) Uani 1 1 d . . . H4 H 0.7659 0.1717 0.0165 0.056 Uiso 1 1 calc R . . C5 C 1.0005(2) 0.48305(11) 0.4486(2) 0.0400(6) Uani 1 1 d . . . H5A H 1.0871 0.4735 0.4624 0.048 Uiso 1 1 calc R . . H5B H 0.9666 0.5115 0.3840 0.048 Uiso 1 1 calc R . . C6 C 0.6527(3) 0.10083(14) 0.0192(3) 0.0604(9) Uani 1 1 d . . . H6 H 0.6526 0.0793 -0.0434 0.072 Uiso 1 1 calc R . . C7 C 0.6578(3) 0.16608(13) 0.1985(2) 0.0486(7) Uani 1 1 d . . . H7 H 0.6592 0.1884 0.2608 0.058 Uiso 1 1 calc R . . C8 C 0.5879(3) 0.11118(14) 0.1669(2) 0.0574(8) Uani 1 1 d . . . H8 H 0.5429 0.0972 0.2072 0.069 Uiso 1 1 calc R . . C9 C 0.5843(3) 0.07703(15) 0.0762(3) 0.0661(10) Uani 1 1 d . . . C10 C 0.5078(6) 0.0161(2) 0.0420(4) 0.149(3) Uani 1 1 d . . . H10A H 0.5438 -0.0126 0.1063 0.179 Uiso 1 1 calc R . . H10B H 0.4241 0.0269 0.0353 0.179 Uiso 1 1 calc R . . N2 N 0.77274(19) 0.63707(9) 0.35560(17) 0.0405(5) Uani 1 1 d . . . O3 O 0.3385(2) 0.12340(11) -0.30269(19) 0.0688(7) Uani 1 1 d . . . O4 O 0.6466(2) 0.53064(10) 0.28262(18) 0.0583(6) Uani 1 1 d . . . O5 O 0.7261(2) 0.52411(10) 0.15538(17) 0.0604(6) Uani 1 1 d . . . C13 C 0.4216(2) 0.21490(12) -0.1939(2) 0.0423(6) Uani 1 1 d . . . H13A H 0.3917 0.2429 -0.2594 0.051 Uiso 1 1 calc R . . H13B H 0.5058 0.2009 -0.1807 0.051 Uiso 1 1 calc R . . C14 C 0.5875(2) 0.40910(12) 0.0600(2) 0.0409(6) Uani 1 1 d . . . H14A H 0.6744 0.3982 0.0775 0.049 Uiso 1 1 calc R . . H14B H 0.5573 0.4371 -0.0054 0.049 Uiso 1 1 calc R . . O6 O 0.2708(2) 0.14450(11) -0.17257(19) 0.0752(7) Uani 1 1 d . . . C15 C 0.5099(3) 0.31158(12) -0.0682(2) 0.0440(6) Uani 1 1 d . . . H15A H 0.4794 0.3388 -0.1347 0.053 Uiso 1 1 calc R . . H15B H 0.5958 0.2993 -0.0523 0.053 Uiso 1 1 calc R . . C16 C 0.6591(2) 0.50343(11) 0.1966(2) 0.0397(6) Uani 1 1 d . . . C17 C 0.9081(3) 0.71681(13) 0.3387(2) 0.0492(7) Uani 1 1 d . . . H17 H 0.9530 0.7324 0.2994 0.059 Uiso 1 1 calc R . . N3 N 1.2008(2) 1.01906(10) 0.65175(19) 0.0492(6) Uani 1 1 d . . . C18 C 0.4283(3) 0.25233(12) -0.0922(2) 0.0429(6) Uani 1 1 d . . . H18A H 0.4612 0.2248 -0.0262 0.052 Uiso 1 1 calc R . . H18B H 0.3437 0.2649 -0.1041 0.052 Uiso 1 1 calc R . . C19 C 0.9117(3) 0.74872(12) 0.4322(2) 0.0470(7) Uani 1 1 d . . . C20 C 0.5812(3) 0.44358(12) 0.1592(2) 0.0462(7) Uani 1 1 d . . . H20A H 0.4939 0.4545 0.1400 0.055 Uiso 1 1 calc R . . H20B H 0.6080 0.4143 0.2228 0.055 Uiso 1 1 calc R . . C21 C 0.8388(3) 0.66220(13) 0.3033(2) 0.0455(6) Uani 1 1 d . . . H21 H 0.8376 0.6416 0.2395 0.055 Uiso 1 1 calc R . . C22 C 1.0605(3) 0.90675(13) 0.5896(2) 0.0493(7) Uani 1 1 d . . . C23 C 0.5087(3) 0.34869(12) 0.0318(2) 0.0468(7) Uani 1 1 d . . . H23A H 0.4222 0.3600 0.0157 0.056 Uiso 1 1 calc R . . H23B H 0.5393 0.3211 0.0978 0.056 Uiso 1 1 calc R . . C24 C 0.3366(3) 0.15758(12) -0.2200(2) 0.0421(6) Uani 1 1 d . . . C25 C 0.9825(3) 0.84606(15) 0.5583(3) 0.0665(9) Uani 1 1 d . . . H25A H 1.0092 0.8192 0.6250 0.080 Uiso 1 1 calc R . . H25B H 0.8950 0.8574 0.5375 0.080 Uiso 1 1 calc R . . C26 C 0.7759(2) 0.66721(12) 0.4466(2) 0.0449(6) Uani 1 1 d . . . H26 H 0.7304 0.6503 0.4844 0.054 Uiso 1 1 calc R . . C27 C 0.9893(3) 0.80920(15) 0.4677(3) 0.0679(10) Uani 1 1 d . . . H27A H 1.0768 0.7978 0.4894 0.082 Uiso 1 1 calc R . . H27B H 0.9643 0.8367 0.4018 0.082 Uiso 1 1 calc R . . C28 C 0.8438(3) 0.72259(13) 0.4873(2) 0.0485(7) Uani 1 1 d . . . H28 H 0.8440 0.7423 0.5515 0.058 Uiso 1 1 calc R . . C29 C 1.0662(3) 0.94273(14) 0.6800(3) 0.0577(8) Uani 1 1 d . . . H29 H 1.0225 0.9299 0.7221 0.069 Uiso 1 1 calc R . . C30 C 1.1365(3) 0.99761(14) 0.7080(2) 0.0557(8) Uani 1 1 d . . . H30 H 1.1393 1.0211 0.7697 0.067 Uiso 1 1 calc R . . C31 C 1.1957(3) 0.98510(13) 0.5641(2) 0.0528(7) Uani 1 1 d . . . H31 H 1.2397 0.9996 0.5233 0.063 Uiso 1 1 calc R . . C32 C 1.1276(3) 0.92908(13) 0.5307(2) 0.0534(8) Uani 1 1 d . . . H32 H 1.1268 0.9064 0.4689 0.064 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0657(13) 0.0448(11) 0.0595(12) -0.0261(9) 0.0401(10) -0.0227(10) N1 0.0488(13) 0.0368(12) 0.0449(12) -0.0119(9) 0.0232(10) -0.0097(10) O2 0.1091(18) 0.0660(14) 0.0718(14) -0.0350(11) 0.0659(14) -0.0486(13) C1 0.0431(14) 0.0325(13) 0.0399(13) -0.0099(10) 0.0192(11) -0.0094(10) C2 0.0432(14) 0.0360(14) 0.0379(13) -0.0085(10) 0.0192(11) -0.0046(11) C3 0.0447(14) 0.0340(13) 0.0346(13) -0.0092(10) 0.0168(11) -0.0081(11) C4 0.0577(17) 0.0436(15) 0.0499(15) -0.0103(12) 0.0329(14) -0.0170(13) C5 0.0503(15) 0.0335(13) 0.0370(13) -0.0094(10) 0.0190(11) -0.0109(11) C6 0.084(2) 0.0547(18) 0.0613(18) -0.0310(15) 0.0494(17) -0.0288(16) C7 0.0616(18) 0.0479(16) 0.0469(15) -0.0160(12) 0.0332(14) -0.0123(13) C8 0.071(2) 0.0550(18) 0.0646(19) -0.0151(15) 0.0466(17) -0.0250(15) C9 0.088(2) 0.0556(19) 0.076(2) -0.0316(16) 0.0559(19) -0.0431(17) C10 0.243(6) 0.113(4) 0.164(5) -0.097(3) 0.158(5) -0.139(4) N2 0.0448(12) 0.0329(11) 0.0442(12) -0.0099(9) 0.0189(10) -0.0091(9) O3 0.0927(17) 0.0531(13) 0.0859(16) -0.0412(12) 0.0624(14) -0.0392(12) O4 0.0717(14) 0.0467(12) 0.0753(14) -0.0308(10) 0.0492(12) -0.0244(10) O5 0.0782(14) 0.0535(12) 0.0665(13) -0.0226(10) 0.0468(12) -0.0284(11) C13 0.0498(16) 0.0354(14) 0.0423(14) -0.0097(11) 0.0198(12) -0.0115(11) C14 0.0465(15) 0.0335(13) 0.0414(13) -0.0089(11) 0.0171(12) -0.0094(11) O6 0.1059(18) 0.0709(15) 0.0760(15) -0.0372(12) 0.0648(14) -0.0486(13) C15 0.0545(16) 0.0377(14) 0.0392(14) -0.0119(11) 0.0191(12) -0.0123(12) C16 0.0411(14) 0.0317(13) 0.0469(14) -0.0084(11) 0.0188(12) -0.0043(11) C17 0.0564(17) 0.0466(16) 0.0566(17) -0.0076(13) 0.0353(14) -0.0118(13) N3 0.0580(14) 0.0380(12) 0.0571(14) -0.0182(10) 0.0293(12) -0.0173(11) C18 0.0503(16) 0.0386(14) 0.0405(13) -0.0133(11) 0.0195(12) -0.0114(12) C19 0.0522(17) 0.0341(14) 0.0584(17) -0.0118(12) 0.0269(14) -0.0140(12) C20 0.0503(16) 0.0398(15) 0.0536(16) -0.0162(12) 0.0266(13) -0.0132(12) C21 0.0545(16) 0.0436(15) 0.0440(15) -0.0111(12) 0.0262(13) -0.0058(12) C22 0.0577(17) 0.0409(15) 0.0571(16) -0.0183(13) 0.0315(14) -0.0185(13) C23 0.0559(17) 0.0391(15) 0.0476(15) -0.0156(12) 0.0239(13) -0.0137(12) C24 0.0498(15) 0.0359(14) 0.0414(14) -0.0104(11) 0.0199(12) -0.0073(11) C25 0.085(2) 0.0553(19) 0.078(2) -0.0281(16) 0.0518(19) -0.0344(17) C26 0.0500(16) 0.0414(15) 0.0499(15) -0.0079(12) 0.0273(13) -0.0128(12) C27 0.082(2) 0.0536(19) 0.085(2) -0.0310(17) 0.052(2) -0.0344(17) C28 0.0572(17) 0.0459(16) 0.0503(16) -0.0191(12) 0.0304(14) -0.0135(13) C29 0.072(2) 0.0546(18) 0.0644(18) -0.0204(15) 0.0462(17) -0.0238(15) C30 0.072(2) 0.0500(17) 0.0560(17) -0.0261(14) 0.0372(16) -0.0174(15) C31 0.0609(18) 0.0473(16) 0.0594(17) -0.0156(13) 0.0342(15) -0.0186(14) C32 0.069(2) 0.0473(16) 0.0547(17) -0.0233(13) 0.0368(15) -0.0188(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.313(3) . ? O1 H1O 0.94(4) . ? N1 C4 1.328(3) . ? N1 C7 1.332(3) . ? O2 C2 1.198(3) . ? C1 C2 1.506(3) . ? C1 C3 1.516(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C3 C5 1.516(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C6 1.376(3) . ? C4 H4 0.9300 . ? C5 C5 1.518(4) 3_766 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C9 1.388(4) . ? C6 H6 0.9300 . ? C7 C8 1.370(4) . ? C7 H7 0.9300 . ? C8 C9 1.366(4) . ? C8 H8 0.9300 . ? C9 C10 1.514(4) . ? C10 C10 1.230(7) 3_655 ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? N2 C26 1.327(3) . ? N2 C21 1.331(3) . ? O3 C24 1.300(3) . ? O3 H3O 0.89(4) . ? O4 C16 1.316(3) . ? O4 H4O 0.96(4) . ? O5 C16 1.198(3) . ? C13 C24 1.502(3) . ? C13 C18 1.511(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C20 1.506(3) . ? C14 C23 1.516(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? O6 C24 1.200(3) . ? C15 C18 1.515(3) . ? C15 C23 1.520(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C20 1.505(3) . ? C17 C21 1.365(4) . ? C17 C19 1.373(3) . ? C17 H17 0.9300 . ? N3 C31 1.323(3) . ? N3 C30 1.325(3) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C28 1.383(4) . ? C19 C27 1.512(4) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21 0.9300 . ? C22 C29 1.374(4) . ? C22 C32 1.384(4) . ? C22 C25 1.517(4) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C25 C27 1.438(4) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C28 1.380(3) . ? C26 H26 0.9300 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28 0.9300 . ? C29 C30 1.370(4) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 C32 1.381(4) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 H1O 110(2) . . ? C4 N1 C7 117.4(2) . . ? C2 C1 C3 113.92(19) . . ? C2 C1 H1A 108.8 . . ? C3 C1 H1A 108.8 . . ? C2 C1 H1B 108.8 . . ? C3 C1 H1B 108.8 . . ? H1A C1 H1B 107.7 . . ? O2 C2 O1 123.1(2) . . ? O2 C2 C1 124.4(2) . . ? O1 C2 C1 112.6(2) . . ? C1 C3 C5 113.76(19) . . ? C1 C3 H3A 108.8 . . ? C5 C3 H3A 108.8 . . ? C1 C3 H3B 108.8 . . ? C5 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? N1 C4 C6 122.6(2) . . ? N1 C4 H4 118.7 . . ? C6 C4 H4 118.7 . . ? C5 C5 C3 113.1(2) 3_766 . ? C5 C5 H5A 108.9 3_766 . ? C3 C5 H5A 108.9 . . ? C5 C5 H5B 108.9 3_766 . ? C3 C5 H5B 108.9 . . ? H5A C5 H5B 107.8 . . ? C4 C6 C9 119.8(2) . . ? C4 C6 H6 120.1 . . ? C9 C6 H6 120.1 . . ? N1 C7 C8 123.3(2) . . ? N1 C7 H7 118.4 . . ? C8 C7 H7 118.4 . . ? C9 C8 C7 119.8(2) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C6 117.2(2) . . ? C8 C9 C10 119.7(3) . . ? C6 C9 C10 123.1(3) . . ? C10 C10 C9 124.9(5) 3_655 . ? C10 C10 H10A 106.1 3_655 . ? C9 C10 H10A 106.1 . . ? C10 C10 H10B 106.1 3_655 . ? C9 C10 H10B 106.1 . . ? H10A C10 H10B 106.3 . . ? C26 N2 C21 117.5(2) . . ? C24 O3 H3O 109(2) . . ? C16 O4 H4O 112(2) . . ? C24 C13 C18 113.6(2) . . ? C24 C13 H13A 108.8 . . ? C18 C13 H13A 108.8 . . ? C24 C13 H13B 108.8 . . ? C18 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? C20 C14 C23 111.4(2) . . ? C20 C14 H14A 109.3 . . ? C23 C14 H14A 109.3 . . ? C20 C14 H14B 109.3 . . ? C23 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? C18 C15 C23 111.4(2) . . ? C18 C15 H15A 109.3 . . ? C23 C15 H15A 109.3 . . ? C18 C15 H15B 109.3 . . ? C23 C15 H15B 109.3 . . ? H15A C15 H15B 108.0 . . ? O5 C16 O4 123.2(2) . . ? O5 C16 C20 125.1(2) . . ? O4 C16 C20 111.7(2) . . ? C21 C17 C19 120.1(2) . . ? C21 C17 H17 120.0 . . ? C19 C17 H17 120.0 . . ? C31 N3 C30 117.4(2) . . ? C13 C18 C15 113.8(2) . . ? C13 C18 H18A 108.8 . . ? C15 C18 H18A 108.8 . . ? C13 C18 H18B 108.8 . . ? C15 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? C17 C19 C28 117.0(2) . . ? C17 C19 C27 118.1(2) . . ? C28 C19 C27 124.9(2) . . ? C16 C20 C14 115.9(2) . . ? C16 C20 H20A 108.3 . . ? C14 C20 H20A 108.3 . . ? C16 C20 H20B 108.3 . . ? C14 C20 H20B 108.3 . . ? H20A C20 H20B 107.4 . . ? N2 C21 C17 123.2(2) . . ? N2 C21 H21 118.4 . . ? C17 C21 H21 118.4 . . ? C29 C22 C32 116.8(2) . . ? C29 C22 C25 119.9(2) . . ? C32 C22 C25 123.3(2) . . ? C14 C23 C15 114.3(2) . . ? C14 C23 H23A 108.7 . . ? C15 C23 H23A 108.7 . . ? C14 C23 H23B 108.7 . . ? C15 C23 H23B 108.7 . . ? H23A C23 H23B 107.6 . . ? O6 C24 O3 122.3(2) . . ? O6 C24 C13 124.8(2) . . ? O3 C24 C13 112.9(2) . . ? C27 C25 C22 115.9(2) . . ? C27 C25 H25A 108.3 . . ? C22 C25 H25A 108.3 . . ? C27 C25 H25B 108.3 . . ? C22 C25 H25B 108.3 . . ? H25A C25 H25B 107.4 . . ? N2 C26 C28 122.6(2) . . ? N2 C26 H26 118.7 . . ? C28 C26 H26 118.7 . . ? C25 C27 C19 118.0(3) . . ? C25 C27 H27A 107.8 . . ? C19 C27 H27A 107.8 . . ? C25 C27 H27B 107.8 . . ? C19 C27 H27B 107.8 . . ? H27A C27 H27B 107.1 . . ? C26 C28 C19 119.7(2) . . ? C26 C28 H28 120.1 . . ? C19 C28 H28 120.1 . . ? C30 C29 C22 119.8(3) . . ? C30 C29 H29 120.1 . . ? C22 C29 H29 120.1 . . ? N3 C30 C29 123.5(2) . . ? N3 C30 H30 118.2 . . ? C29 C30 H30 118.2 . . ? N3 C31 C32 122.7(2) . . ? N3 C31 H31 118.6 . . ? C32 C31 H31 118.6 . . ? C31 C32 C22 119.8(2) . . ? C31 C32 H32 120.1 . . ? C22 C32 H32 120.1 . . ? _diffrn_measured_fraction_theta_max 0.850 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.485 _refine_diff_density_min -0.541 _refine_diff_density_rms 0.044 # Attachment '- 1C9.CIF' data_1.C9 _database_code_depnum_ccdc_archive 'CCDC 763739' #TrackingRef '- 1C9.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H28 N2 O4' _chemical_formula_weight 372.45 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 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 10.656(3) _cell_length_b 8.4290(10) _cell_length_c 22.310(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.851(4) _cell_angle_gamma 90.00 _cell_volume 1974.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1768 _diffrn_reflns_av_R_equivalents 0.0106 _diffrn_reflns_av_sigmaI/netI 0.0147 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 24.97 _reflns_number_total 1720 _reflns_number_gt 1292 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0725P)^2^+0.9579P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0188(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1720 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1291 _refine_ls_wR_factor_gt 0.1152 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 C1 C 0.63981(15) 0.4391(2) 0.56129(8) 0.0529(5) Uani 1 1 d . . . H1 H 0.5586 0.4816 0.5591 0.064 Uiso 1 1 calc R . . C2 C 0.72277(15) 0.5132(2) 0.52976(8) 0.0511(5) Uani 1 1 d . . . H2 H 0.6968 0.6023 0.5063 0.061 Uiso 1 1 calc R . . C3 C 0.84520(14) 0.45528(18) 0.53292(7) 0.0415(4) Uani 1 1 d . . . C4 C 0.87540(15) 0.3222(2) 0.56777(8) 0.0486(4) Uani 1 1 d . . . H4 H 0.9564 0.2783 0.5714 0.058 Uiso 1 1 calc R . . C5 C 0.78563(15) 0.2530(2) 0.59749(8) 0.0507(4) Uani 1 1 d . . . H5 H 0.8082 0.1621 0.6205 0.061 Uiso 1 1 calc R . . C6 C 0.93601(14) 0.5389(2) 0.49879(8) 0.0485(4) Uani 1 1 d . . . H6A H 0.8959 0.5480 0.4565 0.058 Uiso 1 1 calc R . . H6B H 0.9495 0.6456 0.5149 0.058 Uiso 1 1 calc R . . C7 C 0.39831(15) 0.2529(2) 0.65364(7) 0.0455(4) Uani 1 1 d . . . C8 C 0.31061(15) 0.1751(2) 0.69053(8) 0.0474(4) Uani 1 1 d . . . H8A H 0.3598 0.1452 0.7296 0.057 Uiso 1 1 calc R . . H8B H 0.2782 0.0782 0.6700 0.057 Uiso 1 1 calc R . . C9 C 0.19928(16) 0.2732(2) 0.70175(9) 0.0556(5) Uani 1 1 d . . . H9A H 0.1582 0.3195 0.6636 0.067 Uiso 1 1 calc R . . H9B H 0.2300 0.3594 0.7292 0.067 Uiso 1 1 calc R . . C10 C 0.10245(15) 0.1780(2) 0.72870(8) 0.0510(5) Uani 1 1 d . . . H10A H 0.0622 0.1029 0.6984 0.061 Uiso 1 1 calc R . . H10B H 0.1466 0.1175 0.7629 0.061 Uiso 1 1 calc R . . O2 O 0.37146(14) 0.36503(18) 0.62122(7) 0.0787(5) Uani 1 1 d . . . C11 C 0.0000 0.2763(3) 0.7500 0.0521(6) Uani 1 2 d S . . H11A H -0.0391 0.3442 0.7169 0.063 Uiso 0.50 1 calc PR . . H11B H 0.0391 0.3442 0.7831 0.063 Uiso 0.50 1 calc PR . . O1 O 0.50792(12) 0.17985(17) 0.65872(6) 0.0639(4) Uani 1 1 d . . . H100 H 0.560(2) 0.237(3) 0.6371(12) 0.096 Uiso 1 1 d . . . N1 N 0.66918(12) 0.31014(17) 0.59472(6) 0.0485(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0354(8) 0.0594(11) 0.0674(12) 0.0025(9) 0.0184(8) 0.0012(8) C2 0.0403(9) 0.0519(10) 0.0634(11) 0.0104(8) 0.0156(8) 0.0029(7) C3 0.0360(8) 0.0451(9) 0.0456(9) -0.0013(7) 0.0131(6) -0.0050(6) C4 0.0334(8) 0.0559(10) 0.0590(10) 0.0064(8) 0.0146(7) 0.0012(7) C5 0.0455(9) 0.0537(10) 0.0555(10) 0.0093(8) 0.0163(7) -0.0019(8) C6 0.0382(9) 0.0525(10) 0.0584(10) 0.0078(8) 0.0183(7) -0.0031(7) C7 0.0410(9) 0.0500(9) 0.0477(9) 0.0027(8) 0.0141(7) -0.0016(7) C8 0.0401(9) 0.0523(10) 0.0536(10) 0.0049(8) 0.0189(7) 0.0000(7) C9 0.0440(9) 0.0522(10) 0.0766(12) 0.0033(9) 0.0275(8) 0.0004(8) C10 0.0424(10) 0.0522(10) 0.0633(11) 0.0014(8) 0.0233(8) -0.0004(7) O2 0.0656(9) 0.0776(10) 0.1024(12) 0.0414(9) 0.0416(8) 0.0176(7) C11 0.0413(12) 0.0516(14) 0.0681(15) 0.000 0.0227(11) 0.000 O1 0.0411(7) 0.0788(9) 0.0784(9) 0.0278(7) 0.0289(6) 0.0086(6) N1 0.0396(8) 0.0573(9) 0.0521(8) -0.0005(7) 0.0183(6) -0.0072(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.325(2) . ? C1 C2 1.371(2) . ? C1 H1 0.9300 . ? C2 C3 1.384(2) . ? C2 H2 0.9300 . ? C3 C4 1.372(2) . ? C3 C6 1.505(2) . ? C4 C5 1.383(2) . ? C4 H4 0.9300 . ? C5 N1 1.323(2) . ? C5 H5 0.9300 . ? C6 C6 1.506(3) 5_766 ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 O2 1.195(2) . ? C7 O1 1.308(2) . ? C7 C8 1.498(2) . ? C8 C9 1.502(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.511(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.511(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C10 1.511(2) 2_556 ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? O1 H100 0.93(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 N1 C1 C2 123.48(15) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C1 C2 C3 119.88(16) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 116.45(14) . . ? C4 C3 C6 124.14(14) . . ? C2 C3 C6 119.41(15) . . ? C3 C4 C5 120.16(15) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? N1 C5 C4 123.00(17) . . ? N1 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? C6 C6 C3 115.75(18) 5_766 . ? C6 C6 H6A 108.3 5_766 . ? C3 C6 H6A 108.3 . . ? C6 C6 H6B 108.3 5_766 . ? C3 C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? O2 C7 O1 122.86(15) . . ? O2 C7 C8 124.86(15) . . ? O1 C7 C8 112.22(15) . . ? C7 C8 C9 115.80(14) . . ? C7 C8 H8A 108.3 . . ? C9 C8 H8A 108.3 . . ? C7 C8 H8B 108.3 . . ? C9 C8 H8B 108.3 . . ? H8A C8 H8B 107.4 . . ? C8 C9 C10 112.72(15) . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9B 109.0 . . ? C10 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 114.40(15) . . ? C11 C10 H10A 108.7 . . ? C9 C10 H10A 108.7 . . ? C11 C10 H10B 108.7 . . ? C9 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C10 C11 C10 113.5(2) . 2_556 ? C10 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 2_556 . ? C10 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 2_556 . ? H11A C11 H11B 107.7 . . ? C7 O1 H100 108.3(15) . . ? C5 N1 C1 117.02(13) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.245 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.044 # Attachment '- 2C10.CIF' data_2.C10 _database_code_depnum_ccdc_archive 'CCDC 763740' #TrackingRef '- 2C10.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H32 N2 O4' _chemical_formula_weight 400.51 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 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 12.661(3) _cell_length_b 10.1290(10) _cell_length_c 17.361(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.130(10) _cell_angle_gamma 90.00 _cell_volume 2223.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.197 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5603 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0941 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1935 _reflns_number_gt 708 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0999P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1935 _refine_ls_number_parameters 132 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2667 _refine_ls_R_factor_gt 0.0934 _refine_ls_wR_factor_ref 0.2491 _refine_ls_wR_factor_gt 0.1766 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 N1 N 0.1782(4) -0.0488(5) 1.0198(2) 0.0853(15) Uani 1 1 d . . . C1 C 0.1670(5) 0.0787(7) 1.0133(4) 0.125(3) Uani 1 1 d . . . H1 H 0.1907 0.1314 1.0545 0.150 Uiso 1 1 calc R . . C2 C 0.1220(6) 0.1391(6) 0.9488(4) 0.148(3) Uani 1 1 d . . . H2 H 0.1155 0.2306 0.9484 0.178 Uiso 1 1 calc R . . C3 C 0.0874(4) 0.0715(6) 0.8869(3) 0.0755(16) Uani 1 1 d . . . C4 C 0.1027(5) -0.0591(6) 0.8925(3) 0.103(2) Uani 1 1 d . . . H4 H 0.0835 -0.1132 0.8508 0.123 Uiso 1 1 calc R . . C5 C 0.1466(5) -0.1141(5) 0.9593(3) 0.116(3) Uani 1 1 d . . . H5 H 0.1539 -0.2055 0.9608 0.139 Uiso 1 1 calc R . . C6 C 0.0396(4) 0.1397(5) 0.8166(3) 0.0957(19) Uani 1 1 d . . . H6A H 0.0921 0.1996 0.7977 0.115 Uiso 1 1 calc R . . H6B H -0.0192 0.1930 0.8323 0.115 Uiso 1 1 calc R . . C7 C 0.0000 0.0530(6) 0.7500 0.072(2) Uani 1 2 d S . . H7A H -0.0568 -0.0031 0.7661 0.086 Uiso 0.50 1 calc PR . . H7B H 0.0568 -0.0031 0.7339 0.086 Uiso 0.50 1 calc PR . . O1 O -0.2640(3) -0.1433(3) 0.34821(17) 0.1184(17) Uani 1 1 d . . . H100 H -0.2389 -0.1077 0.3873 0.178 Uiso 1 1 d R . . O2 O -0.2924(4) 0.0607(4) 0.3136(2) 0.1184(17) Uani 1 1 d . . . C8 C -0.2973(4) -0.0534(6) 0.2996(3) 0.0745(17) Uani 1 1 d . . . C9 C -0.3450(4) -0.1088(5) 0.2266(2) 0.0808(17) Uani 1 1 d . . . H9A H -0.4005 -0.1699 0.2392 0.097 Uiso 1 1 calc R . . H9B H -0.2912 -0.1592 0.2019 0.097 Uiso 1 1 calc R . . C10 C -0.3909(4) -0.0109(4) 0.1696(2) 0.0695(14) Uani 1 1 d . . . H10A H -0.4482 0.0356 0.1926 0.083 Uiso 1 1 calc R . . H10B H -0.3369 0.0536 0.1590 0.083 Uiso 1 1 calc R . . C11 C -0.4318(4) -0.0700(5) 0.0950(2) 0.0735(15) Uani 1 1 d . . . H11A H -0.3740 -0.1143 0.0713 0.088 Uiso 1 1 calc R . . H11B H -0.4842 -0.1363 0.1058 0.088 Uiso 1 1 calc R . . C12 C -0.4804(4) 0.0265(4) 0.0386(2) 0.0745(16) Uani 1 1 d . . . H12A H -0.4285 0.0946 0.0300 0.089 Uiso 1 1 calc R . . H12B H -0.5394 0.0685 0.0622 0.089 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.085(4) 0.111(4) 0.059(3) -0.025(3) -0.003(2) -0.017(3) C1 0.118(6) 0.132(6) 0.116(5) -0.082(5) -0.063(4) 0.043(5) C2 0.174(8) 0.112(5) 0.145(5) -0.069(5) -0.117(6) 0.062(5) C3 0.061(4) 0.076(4) 0.087(4) -0.021(3) -0.019(3) 0.011(3) C4 0.160(7) 0.088(4) 0.056(3) -0.010(3) -0.028(3) -0.031(4) C5 0.194(8) 0.088(4) 0.061(3) 0.001(3) -0.037(4) -0.046(4) C6 0.079(5) 0.087(4) 0.117(4) -0.015(3) -0.038(4) 0.009(3) C7 0.069(5) 0.059(5) 0.084(4) 0.000 -0.017(4) 0.000 O1 0.181(5) 0.103(3) 0.068(2) 0.014(2) -0.025(2) 0.045(3) O2 0.163(5) 0.095(3) 0.091(3) 0.018(2) -0.049(3) -0.001(3) C8 0.078(4) 0.089(4) 0.057(3) 0.022(3) 0.000(3) 0.027(4) C9 0.083(4) 0.103(4) 0.055(3) 0.012(3) 0.000(3) 0.031(3) C10 0.073(4) 0.084(3) 0.052(3) 0.018(2) 0.002(3) 0.009(3) C11 0.079(4) 0.088(4) 0.053(3) 0.008(2) -0.002(3) 0.018(3) C12 0.087(4) 0.080(4) 0.056(2) 0.012(2) -0.003(3) 0.015(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 N1 C5 1.286(5) . ? N1 C1 1.303(7) . ? C1 C2 1.372(7) . ? C1 H1 0.9300 . ? C2 C3 1.328(6) . ? C2 H2 0.9300 . ? C3 C4 1.340(7) . ? C3 C6 1.501(6) . ? C4 C5 1.375(6) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.515(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C6 1.515(5) 2_556 ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? O1 C8 1.297(5) . ? O1 H100 0.8175 . ? O2 C8 1.181(5) . ? C8 C9 1.484(6) . ? C9 C10 1.496(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.493(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.491(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C12 1.503(8) 5_455 ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C1 114.3(5) . . ? N1 C1 C2 123.5(5) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C3 C2 C1 122.2(6) . . ? C3 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? C2 C3 C4 114.3(5) . . ? C2 C3 C6 121.4(6) . . ? C4 C3 C6 124.3(5) . . ? C3 C4 C5 120.7(5) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? N1 C5 C4 125.0(5) . . ? N1 C5 H5 117.5 . . ? C4 C5 H5 117.5 . . ? C3 C6 C7 117.1(5) . . ? C3 C6 H6A 108.0 . . ? C7 C6 H6A 108.0 . . ? C3 C6 H6B 108.0 . . ? C7 C6 H6B 108.0 . . ? H6A C6 H6B 107.3 . . ? C6 C7 C6 109.1(6) . 2_556 ? C6 C7 H7A 109.9 . . ? C6 C7 H7A 109.9 2_556 . ? C6 C7 H7B 109.9 . . ? C6 C7 H7B 109.9 2_556 . ? H7A C7 H7B 108.3 . . ? C8 O1 H100 109.2 . . ? O2 C8 O1 122.8(5) . . ? O2 C8 C9 124.0(5) . . ? O1 C8 C9 113.2(5) . . ? C8 C9 C10 116.1(4) . . ? C8 C9 H9A 108.3 . . ? C10 C9 H9A 108.3 . . ? C8 C9 H9B 108.3 . . ? C10 C9 H9B 108.3 . . ? H9A C9 H9B 107.4 . . ? C11 C10 C9 114.3(4) . . ? C11 C10 H10A 108.7 . . ? C9 C10 H10A 108.7 . . ? C11 C10 H10B 108.7 . . ? C9 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C12 C11 C10 114.7(4) . . ? C12 C11 H11A 108.6 . . ? C10 C11 H11A 108.6 . . ? C12 C11 H11B 108.6 . . ? C10 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? C11 C12 C12 117.1(5) . 5_455 ? C11 C12 H12A 108.0 . . ? C12 C12 H12A 108.0 5_455 . ? C11 C12 H12B 108.0 . . ? C12 C12 H12B 108.0 5_455 . ? H12A C12 H12B 107.3 . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.155 _refine_diff_density_min -0.114 _refine_diff_density_rms 0.033 # Attachment '- 2C5.CIF' data_2.C5 _database_code_depnum_ccdc_archive 'CCDC 763741' #TrackingRef '- 2C5.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 N2 O4' _chemical_formula_weight 330.38 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)/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 5.4308(2) _cell_length_b 20.7179(7) _cell_length_c 15.4813(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.205(3) _cell_angle_gamma 90.00 _cell_volume 1740.59(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15427 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0454 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3411 _reflns_number_gt 2172 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0529P)^2^+0.7004P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3411 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1530 _refine_ls_R_factor_gt 0.0882 _refine_ls_wR_factor_ref 0.1685 _refine_ls_wR_factor_gt 0.1461 _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_restrained_S_all 1.159 _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 N1 N -1.4691(4) 0.37706(12) -0.42110(16) 0.0490(7) Uani 1 1 d . . . N2 N -0.0791(4) 0.39613(12) 0.03760(17) 0.0543(7) Uani 1 1 d . . . C6 C -1.4873(5) 0.31619(15) -0.39654(19) 0.0494(8) Uani 1 1 d . . . H6 H -1.6163 0.2915 -0.4200 0.038(7) Uiso 1 1 d R . . C7 C -1.3265(5) 0.28726(14) -0.33796(18) 0.0440(7) Uani 1 1 d . . . H7 H -1.3430 0.2443 -0.3217 0.049(8) Uiso 1 1 d R . . C8 C -1.1312(5) 0.32206(13) -0.30164(17) 0.0384(7) Uani 1 1 d . . . C9 C -1.1137(6) 0.38589(14) -0.3270(2) 0.0557(9) Uani 1 1 d . . . H9 H -0.9848 0.4106 -0.3035 0.065(9) Uiso 1 1 d R . . C10 C -1.2834(6) 0.41070(15) -0.3864(2) 0.0576(9) Uani 1 1 d . . . H10 H -1.2669 0.4537 -0.4026 0.068(10) Uiso 1 1 d R . . C11 C -0.2512(6) 0.42776(16) -0.0082(2) 0.0637(10) Uani 1 1 d . . . H11 H -0.2572 0.4724 -0.0026 0.073(11) Uiso 1 1 d R . . C12 C -0.4205(6) 0.39830(15) -0.0630(2) 0.0587(9) Uani 1 1 d . . . H12 H -0.5400 0.4218 -0.0940 0.063(9) Uiso 1 1 d R . . C13 C -0.4215(5) 0.33179(13) -0.07199(18) 0.0408(7) Uani 1 1 d . . . C14 C -0.2370(5) 0.29969(15) -0.02558(19) 0.0463(8) Uani 1 1 d . . . H14 H -0.2310 0.2550 -0.0311 0.049(9) Uiso 1 1 d R . . C15 C -0.0750(5) 0.33245(16) 0.02759(19) 0.0518(9) Uani 1 1 d . . . H15 H 0.0445 0.3089 0.0586 0.060(9) Uiso 1 1 d R . . C16 C -0.6049(5) 0.29531(13) -0.12788(19) 0.0441(8) Uani 1 1 d . . . H16A H -0.5159 0.2652 -0.1631 0.058(9) Uiso 1 1 d R . . H16B H -0.7043 0.2700 -0.0896 0.042(8) Uiso 1 1 d R . . C17 C -0.7780(5) 0.33437(13) -0.18722(19) 0.0420(7) Uani 1 1 d . . . H17A H -0.8735 0.3638 -0.1530 0.050(9) Uiso 1 1 d R . . H17B H -0.6823 0.3598 -0.2264 0.044(8) Uiso 1 1 d R . . C18 C -0.9505(5) 0.29018(13) -0.23855(19) 0.0424(7) Uani 1 1 d . . . H18A H -1.0434 0.2650 -0.1982 0.049(9) Uiso 1 1 d R . . H18B H -0.8516 0.2603 -0.2707 0.035(7) Uiso 1 1 d R . . O1 O 0.2321(4) 0.06665(10) -0.03506(15) 0.0690(8) Uani 1 1 d . . . H101 H 0.3370 0.0863 -0.0092 0.088(14) Uiso 1 1 d R . . O2 O 0.0492(4) 0.16042(10) -0.06124(16) 0.0704(7) Uani 1 1 d . . . O3 O -0.7550(4) 0.05087(10) -0.35108(16) 0.0757(8) Uani 1 1 d . . . H103 H -0.8464 0.0702 -0.3901 0.097(14) Uiso 1 1 d R . . O4 O -0.6331(4) 0.14973(11) -0.31785(16) 0.0763(8) Uani 1 1 d . . . C1 C 0.0675(5) 0.10370(14) -0.0739(2) 0.0474(8) Uani 1 1 d . . . C2 C -0.0974(6) 0.06545(15) -0.1355(2) 0.0560(9) Uani 1 1 d . . . H2A H -0.1923 0.0352 -0.1025 0.086(13) Uiso 1 1 d R . . H2B H 0.0066 0.0404 -0.1725 0.082(12) Uiso 1 1 d R . . C3 C -0.2735(6) 0.10432(15) -0.1923(2) 0.0539(9) Uani 1 1 d . . . H3A H -0.1820 0.1346 -0.2265 0.079(12) Uiso 1 1 d R . . H3B H -0.3826 0.1288 -0.1565 0.089(13) Uiso 1 1 d R . . C4 C -0.4235(6) 0.06016(15) -0.2520(2) 0.0585(10) Uani 1 1 d . . . H4A H -0.3116 0.0365 -0.2877 0.088(13) Uiso 1 1 d R . . H4B H -0.5070 0.0289 -0.2167 0.079(12) Uiso 1 1 d R . . C5 C -0.6119(5) 0.09282(15) -0.3096(2) 0.0490(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0462(14) 0.0512(16) 0.0484(16) 0.0004(13) -0.0140(12) -0.0013(13) N2 0.0507(16) 0.0571(17) 0.0535(17) -0.0008(14) -0.0187(13) 0.0019(13) C6 0.0446(18) 0.0551(19) 0.047(2) -0.0069(16) -0.0114(16) -0.0101(16) C7 0.0496(18) 0.0416(17) 0.0403(17) -0.0015(14) -0.0034(15) -0.0039(14) C8 0.0366(15) 0.0442(17) 0.0342(16) -0.0051(13) -0.0024(13) -0.0007(14) C9 0.0514(19) 0.0461(19) 0.067(2) 0.0048(16) -0.0254(17) -0.0105(15) C10 0.059(2) 0.0450(19) 0.067(2) 0.0084(17) -0.0205(18) -0.0047(16) C11 0.064(2) 0.046(2) 0.078(3) -0.0058(18) -0.031(2) 0.0056(16) C12 0.0523(19) 0.053(2) 0.068(2) 0.0003(17) -0.0293(18) 0.0088(17) C13 0.0382(16) 0.0444(17) 0.0395(17) 0.0023(14) -0.0009(14) 0.0012(13) C14 0.0441(17) 0.0464(19) 0.0477(19) 0.0078(15) -0.0086(15) 0.0064(14) C15 0.0462(19) 0.064(2) 0.0440(19) 0.0081(17) -0.0168(16) 0.0090(16) C16 0.0421(17) 0.0426(17) 0.0468(18) 0.0033(15) -0.0076(15) 0.0009(15) C17 0.0410(16) 0.0433(17) 0.0409(17) 0.0012(15) -0.0074(14) 0.0001(15) C18 0.0413(17) 0.0418(17) 0.0437(18) -0.0001(15) -0.0035(15) -0.0008(14) O1 0.0670(15) 0.0530(14) 0.0834(18) -0.0095(13) -0.0458(14) 0.0093(12) O2 0.0785(17) 0.0423(13) 0.0879(19) -0.0072(13) -0.0286(14) 0.0071(12) O3 0.0807(17) 0.0555(14) 0.0868(18) -0.0006(13) -0.0486(15) -0.0038(13) O4 0.0763(17) 0.0499(14) 0.099(2) 0.0022(13) -0.0446(15) 0.0022(12) C1 0.0471(18) 0.0450(19) 0.049(2) 0.0001(15) -0.0136(15) 0.0037(15) C2 0.0553(19) 0.0500(19) 0.061(2) 0.0009(18) -0.0211(18) 0.0025(18) C3 0.0508(18) 0.0505(19) 0.059(2) -0.0018(18) -0.0217(17) 0.0003(17) C4 0.056(2) 0.0514(19) 0.066(2) 0.0031(19) -0.0225(19) 0.0010(18) C5 0.0492(18) 0.0453(19) 0.051(2) -0.0011(16) -0.0151(16) -0.0032(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 N1 C6 1.322(3) . ? N1 C10 1.323(3) . ? N2 C11 1.324(4) . ? N2 C15 1.329(4) . ? C6 C7 1.372(4) . ? C6 H6 0.9299 . ? C7 C8 1.384(4) . ? C7 H7 0.9301 . ? C8 C9 1.383(4) . ? C8 C18 1.510(4) . ? C9 C10 1.376(4) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.371(4) . ? C11 H11 0.9299 . ? C12 C13 1.385(4) . ? C12 H12 0.9300 . ? C13 C14 1.381(3) . ? C13 C16 1.499(4) . ? C14 C15 1.363(4) . ? C14 H14 0.9301 . ? C15 H15 0.9300 . ? C16 C17 1.522(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9699 . ? C17 C18 1.514(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9699 . ? C18 H18A 0.9701 . ? C18 H18B 0.9700 . ? O1 C1 1.307(3) . ? O1 H101 0.7957 . ? O2 C1 1.196(3) . ? O3 C5 1.316(3) . ? O3 H103 0.8663 . ? O4 C5 1.191(3) . ? C1 C2 1.508(4) . ? C2 C3 1.507(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.515(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.494(4) . ? C4 H4A 0.9699 . ? C4 H4B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C10 116.7(3) . . ? C11 N2 C15 116.3(3) . . ? N1 C6 C7 123.6(3) . . ? N1 C6 H6 118.5 . . ? C7 C6 H6 117.9 . . ? C6 C7 C8 120.0(3) . . ? C6 C7 H7 122.1 . . ? C8 C7 H7 118.0 . . ? C9 C8 C7 116.3(3) . . ? C9 C8 C18 123.5(2) . . ? C7 C8 C18 120.2(3) . . ? C10 C9 C8 119.7(3) . . ? C10 C9 H9 122.0 . . ? C8 C9 H9 118.3 . . ? N1 C10 C9 123.7(3) . . ? N1 C10 H10 118.3 . . ? C9 C10 H10 118.0 . . ? N2 C11 C12 123.6(3) . . ? N2 C11 H11 118.0 . . ? C12 C11 H11 118.3 . . ? C11 C12 C13 120.3(3) . . ? C11 C12 H12 121.7 . . ? C13 C12 H12 118.0 . . ? C14 C13 C12 115.3(3) . . ? C14 C13 C16 120.7(3) . . ? C12 C13 C16 124.0(2) . . ? C15 C14 C13 120.9(3) . . ? C15 C14 H14 121.8 . . ? C13 C14 H14 117.3 . . ? N2 C15 C14 123.5(3) . . ? N2 C15 H15 118.3 . . ? C14 C15 H15 118.2 . . ? C13 C16 C17 117.5(2) . . ? C13 C16 H16A 108.3 . . ? C17 C16 H16A 108.2 . . ? C13 C16 H16B 107.0 . . ? C17 C16 H16B 108.1 . . ? H16A C16 H16B 107.3 . . ? C18 C17 C16 110.5(2) . . ? C18 C17 H17A 109.4 . . ? C16 C17 H17A 109.6 . . ? C18 C17 H17B 109.7 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? C8 C18 C17 116.7(2) . . ? C8 C18 H18A 108.1 . . ? C17 C18 H18A 108.4 . . ? C8 C18 H18B 107.8 . . ? C17 C18 H18B 108.1 . . ? H18A C18 H18B 107.3 . . ? C1 O1 H101 113.2 . . ? C5 O3 H103 110.3 . . ? O2 C1 O1 124.1(3) . . ? O2 C1 C2 124.7(3) . . ? O1 C1 C2 111.2(3) . . ? C3 C2 C1 115.9(3) . . ? C3 C2 H2A 108.3 . . ? C1 C2 H2A 108.7 . . ? C3 C2 H2B 108.2 . . ? C1 C2 H2B 108.0 . . ? H2A C2 H2B 107.4 . . ? C2 C3 C4 110.3(3) . . ? C2 C3 H3A 109.7 . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3B 109.5 . . ? C4 C3 H3B 109.8 . . ? H3A C3 H3B 108.1 . . ? C5 C4 C3 115.5(3) . . ? C5 C4 H4A 108.5 . . ? C3 C4 H4A 108.6 . . ? C5 C4 H4B 108.3 . . ? C3 C4 H4B 108.2 . . ? H4A C4 H4B 107.5 . . ? O4 C5 O3 123.3(3) . . ? O4 C5 C4 125.0(3) . . ? O3 C5 C4 111.7(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.137 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.037 # Attachment '- 2C6.CIF' data_2.C6 _database_code_depnum_ccdc_archive 'CCDC 763742' #TrackingRef '- 2C6.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H24 N2 O4' _chemical_formula_weight 344.40 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 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 13.7629(8) _cell_length_b 5.3869(4) _cell_length_c 24.640(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.597(6) _cell_angle_gamma 90.00 _cell_volume 1818.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4312 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1586 _reflns_number_gt 1044 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0621P)^2^+0.4972P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1586 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1162 _refine_ls_R_factor_gt 0.0647 _refine_ls_wR_factor_ref 0.1429 _refine_ls_wR_factor_gt 0.1266 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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 O2 O 0.55411(12) 0.0338(4) 0.41482(8) 0.0682(6) Uani 1 1 d . . . C3 C 0.15956(17) 0.2172(5) 0.31189(9) 0.0443(6) Uani 1 1 d . . . N1 N 0.31423(14) -0.0313(4) 0.37030(9) 0.0567(6) Uani 1 1 d . . . C10 C 0.71355(15) -0.1748(5) 0.48199(9) 0.0486(7) Uani 1 1 d . . . H10A H 0.7352 -0.1648 0.4457 0.058 Uiso 1 1 calc R . . H10B H 0.7116 -0.0074 0.4963 0.058 Uiso 1 1 calc R . . C8 C 0.53938(17) -0.1526(5) 0.43912(10) 0.0501(7) Uani 1 1 d . . . C4 C 0.14517(17) 0.0061(5) 0.34175(10) 0.0487(7) Uani 1 1 d . . . H4 H 0.0825 -0.0567 0.3430 0.058 Uiso 1 1 calc R . . C2 C 0.25468(18) 0.2991(5) 0.31251(10) 0.0539(7) Uani 1 1 d . . . H2 H 0.2688 0.4397 0.2928 0.065 Uiso 1 1 calc R . . C9 C 0.61157(16) -0.2836(5) 0.47785(9) 0.0529(7) Uani 1 1 d . . . H9A H 0.6150 -0.4558 0.4667 0.063 Uiso 1 1 calc R . . H9B H 0.5883 -0.2810 0.5138 0.063 Uiso 1 1 calc R . . C7 C 0.0000 0.2054(7) 0.2500 0.0597(10) Uani 1 2 d S . . H7A H -0.0313 0.0992 0.2749 0.072 Uiso 0.50 1 calc PR . . H7B H 0.0313 0.0992 0.2251 0.072 Uiso 0.50 1 calc PR . . O1 O 0.45453(12) -0.2671(4) 0.43318(9) 0.0842(7) Uani 1 1 d . . . H100 H 0.4167 -0.1892 0.4117 0.126 Uiso 1 1 calc R . . C6 C 0.07644(18) 0.3569(5) 0.28197(11) 0.0598(8) Uani 1 1 d . . . H6A H 0.0449 0.4543 0.3084 0.072 Uiso 1 1 calc R . . H6B H 0.1033 0.4724 0.2572 0.072 Uiso 1 1 calc R . . C5 C 0.22340(17) -0.1115(5) 0.36966(10) 0.0511(7) Uani 1 1 d . . . H5 H 0.2118 -0.2548 0.3891 0.061 Uiso 1 1 calc R . . C1 C 0.32807(18) 0.1733(6) 0.34209(11) 0.0616(8) Uani 1 1 d . . . H1 H 0.3913 0.2346 0.3425 0.074 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 O2 0.0522(11) 0.0679(13) 0.0821(14) 0.0321(12) -0.0051(9) 0.0027(10) C3 0.0474(14) 0.0435(14) 0.0401(12) -0.0039(13) -0.0052(11) -0.0004(13) N1 0.0401(12) 0.0610(15) 0.0671(15) 0.0006(13) -0.0047(10) 0.0070(12) C10 0.0446(14) 0.0529(17) 0.0474(13) 0.0081(13) 0.0009(11) 0.0069(12) C8 0.0394(14) 0.0588(18) 0.0523(15) 0.0108(15) 0.0052(12) 0.0082(14) C4 0.0376(13) 0.0509(16) 0.0553(16) -0.0004(15) -0.0069(11) -0.0059(13) C2 0.0512(15) 0.0560(17) 0.0545(15) 0.0073(14) 0.0057(13) -0.0052(15) C9 0.0440(14) 0.0623(18) 0.0516(14) 0.0133(15) 0.0011(12) 0.0078(14) C7 0.049(2) 0.057(2) 0.069(2) 0.000 -0.0160(19) 0.000 O1 0.0417(11) 0.0879(16) 0.1186(17) 0.0468(14) -0.0144(10) -0.0063(12) C6 0.0569(16) 0.0585(18) 0.0585(16) 0.0038(15) -0.0212(14) -0.0019(15) C5 0.0465(15) 0.0476(16) 0.0571(16) 0.0041(14) -0.0058(13) -0.0020(14) C1 0.0374(14) 0.073(2) 0.0743(18) 0.0025(18) 0.0066(14) -0.0043(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 O2 C8 1.197(3) . ? C3 C4 1.379(3) . ? C3 C2 1.380(3) . ? C3 C6 1.501(3) . ? N1 C5 1.321(3) . ? N1 C1 1.327(3) . ? C10 C10 1.509(4) 7_646 ? C10 C9 1.515(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C8 O1 1.316(3) . ? C8 C9 1.487(3) . ? C4 C5 1.375(3) . ? C4 H4 0.9300 . ? C2 C1 1.366(4) . ? C2 H2 0.9300 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C7 C6 1.494(3) . ? C7 C6 1.494(3) 2 ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? O1 H100 0.8200 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C5 H5 0.9300 . ? C1 H1 0.9300 . ? 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 C4 C3 C2 116.3(2) . . ? C4 C3 C6 122.2(2) . . ? C2 C3 C6 121.5(2) . . ? C5 N1 C1 116.7(2) . . ? C10 C10 C9 113.0(3) 7_646 . ? C10 C10 H10A 109.0 7_646 . ? C9 C10 H10A 109.0 . . ? C10 C10 H10B 109.0 7_646 . ? C9 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? O2 C8 O1 122.0(2) . . ? O2 C8 C9 125.7(2) . . ? O1 C8 C9 112.3(2) . . ? C5 C4 C3 120.0(2) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C1 C2 C3 119.9(3) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C8 C9 C10 114.6(2) . . ? C8 C9 H9A 108.6 . . ? C10 C9 H9A 108.6 . . ? C8 C9 H9B 108.6 . . ? C10 C9 H9B 108.6 . . ? H9A C9 H9B 107.6 . . ? C6 C7 C6 113.8(3) . 2 ? C6 C7 H7A 108.8 . . ? C6 C7 H7A 108.8 2 . ? C6 C7 H7B 108.8 . . ? C6 C7 H7B 108.8 2 . ? H7A C7 H7B 107.7 . . ? C8 O1 H100 109.5 . . ? C7 C6 C3 116.7(2) . . ? C7 C6 H6A 108.1 . . ? C3 C6 H6A 108.1 . . ? C7 C6 H6B 108.1 . . ? C3 C6 H6B 108.1 . . ? H6A C6 H6B 107.3 . . ? N1 C5 C4 123.3(2) . . ? N1 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? N1 C1 C2 123.7(2) . . ? N1 C1 H1 118.1 . . ? C2 C1 H1 118.1 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.190 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.033 # Attachment '- 2C7.CIF' data_2.C7 _database_code_depnum_ccdc_archive 'CCDC 763743' #TrackingRef '- 2C7.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H26 N2 O4' _chemical_formula_weight 358.43 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 7.1246(4) _cell_length_b 11.1403(4) _cell_length_c 12.9265(7) _cell_angle_alpha 81.099(4) _cell_angle_beta 84.868(5) _cell_angle_gamma 71.717(4) _cell_volume 961.54(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7249 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0801 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3687 _reflns_number_gt 1631 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0541P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3687 _refine_ls_number_parameters 243 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1632 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1333 _refine_ls_wR_factor_gt 0.1059 _refine_ls_goodness_of_fit_ref 0.911 _refine_ls_restrained_S_all 0.911 _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 H1A H 1.530(4) -0.190(2) 0.525(2) 0.066(9) Uiso 1 1 d . . . H1B H 2.910(4) -0.631(3) 0.964(2) 0.093(12) Uiso 1 1 d . . . C9 C 0.3866(4) 0.0272(2) 0.13346(19) 0.0443(7) Uani 1 1 d . . . C7 C 0.6981(3) -0.0689(2) 0.2420(2) 0.0530(7) Uani 1 1 d . . . H7A H 0.6357 -0.0213 0.2992 0.064 Uiso 1 1 calc R . . H7B H 0.7688 -0.0187 0.1959 0.064 Uiso 1 1 calc R . . O3 O 2.6769(3) -0.70669(17) 0.91246(18) 0.0920(8) Uani 1 1 d . . . C19 C 2.5450(3) -0.4904(2) 0.8374(2) 0.0554(8) Uani 1 1 d . . . H19A H 2.6182 -0.4548 0.7804 0.066 Uiso 1 1 calc R . . H19B H 2.4903 -0.4257 0.8835 0.066 Uiso 1 1 calc R . . O4 O 2.8304(3) -0.56966(17) 0.93294(18) 0.0747(7) Uani 1 1 d . . . C3 C 1.0114(4) -0.1894(2) 0.34380(19) 0.0467(7) Uani 1 1 d . . . O2 O 1.6298(3) -0.17817(16) 0.55747(17) 0.0738(7) Uani 1 1 d . . . C15 C 1.9193(3) -0.2841(2) 0.6455(2) 0.0514(7) Uani 1 1 d . . . H15A H 1.8661 -0.2353 0.7031 0.062 Uiso 1 1 calc R . . H15B H 1.9925 -0.2371 0.5977 0.062 Uiso 1 1 calc R . . C17 C 2.2351(3) -0.3936(2) 0.7385(2) 0.0553(8) Uani 1 1 d . . . H17A H 2.1834 -0.3350 0.7898 0.066 Uiso 1 1 calc R . . H17B H 2.3096 -0.3543 0.6847 0.066 Uiso 1 1 calc R . . O1 O 1.7261(3) -0.38807(16) 0.57279(17) 0.0843(7) Uani 1 1 d . . . C2 C 1.1531(4) -0.3008(2) 0.3822(2) 0.0562(8) Uani 1 1 d . . . H2 H 1.1424 -0.3793 0.3724 0.067 Uiso 1 1 calc R . . C18 C 2.3753(4) -0.5149(2) 0.7917(2) 0.0543(8) Uani 1 1 d . . . H18A H 2.3032 -0.5536 0.8472 0.065 Uiso 1 1 calc R . . H18B H 2.4270 -0.5746 0.7413 0.065 Uiso 1 1 calc R . . C13 C 0.2110(4) 0.0180(2) 0.1054(2) 0.0555(8) Uani 1 1 d . . . H13 H 0.1862 -0.0602 0.1183 0.067 Uiso 1 1 calc R . . C1 C 1.3081(4) -0.2959(2) 0.4344(2) 0.0583(8) Uani 1 1 d . . . H1 H 1.4012 -0.3725 0.4586 0.070 Uiso 1 1 calc R . . C16 C 2.0633(4) -0.4108(2) 0.6887(2) 0.0544(8) Uani 1 1 d . . . H16A H 1.9940 -0.4562 0.7405 0.065 Uiso 1 1 calc R . . H16B H 2.1131 -0.4623 0.6324 0.065 Uiso 1 1 calc R . . C10 C 0.4110(4) 0.1479(2) 0.1119(2) 0.0568(8) Uani 1 1 d . . . H10 H 0.5266 0.1608 0.1292 0.068 Uiso 1 1 calc R . . N1 N 1.3338(3) -0.1877(2) 0.45257(16) 0.0550(6) Uani 1 1 d . . . N2 N 0.0945(3) 0.23795(19) 0.03758(16) 0.0518(6) Uani 1 1 d . . . C12 C 0.0715(4) 0.1229(2) 0.0586(2) 0.0613(8) Uani 1 1 d . . . H12 H -0.0457 0.1128 0.0407 0.074 Uiso 1 1 calc R . . C6 C 0.8434(4) -0.1941(2) 0.2854(2) 0.0603(8) Uani 1 1 d . . . H6A H 0.7698 -0.2421 0.3318 0.072 Uiso 1 1 calc R . . H6B H 0.8983 -0.2420 0.2274 0.072 Uiso 1 1 calc R . . C20 C 2.6878(4) -0.6012(2) 0.8971(2) 0.0507(7) Uani 1 1 d . . . C5 C 1.1999(4) -0.0803(2) 0.4157(2) 0.0601(8) Uani 1 1 d . . . H5 H 1.2153 -0.0034 0.4266 0.072 Uiso 1 1 calc R . . C4 C 1.0403(4) -0.0767(2) 0.3627(2) 0.0571(8) Uani 1 1 d . . . H4 H 0.9504 0.0015 0.3390 0.068 Uiso 1 1 calc R . . C8 C 0.5412(4) -0.0889(2) 0.1821(2) 0.0547(8) Uani 1 1 d . . . H8A H 0.4737 -0.1402 0.2293 0.066 Uiso 1 1 calc R . . H8B H 0.6069 -0.1388 0.1267 0.066 Uiso 1 1 calc R . . C11 C 0.2626(4) 0.2482(2) 0.0648(2) 0.0576(8) Uani 1 1 d . . . H11 H 0.2821 0.3280 0.0514 0.069 Uiso 1 1 calc R . . C14 C 1.7499(4) -0.2916(3) 0.5891(2) 0.0512(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C9 0.0478(17) 0.0418(15) 0.0407(18) -0.0041(12) -0.0104(14) -0.0083(13) C7 0.0451(17) 0.0459(14) 0.066(2) -0.0030(14) -0.0194(15) -0.0080(13) O3 0.0837(15) 0.0471(11) 0.149(2) 0.0180(12) -0.0643(14) -0.0237(11) C19 0.0465(17) 0.0479(14) 0.068(2) 0.0029(14) -0.0215(15) -0.0095(13) O4 0.0648(15) 0.0504(12) 0.110(2) 0.0115(12) -0.0524(14) -0.0159(11) C3 0.0447(17) 0.0451(15) 0.0491(19) -0.0039(13) -0.0110(14) -0.0104(13) O2 0.0598(14) 0.0518(12) 0.1099(19) -0.0028(11) -0.0484(13) -0.0087(11) C15 0.0444(17) 0.0508(15) 0.054(2) -0.0024(13) -0.0126(14) -0.0069(13) C17 0.0462(18) 0.0515(15) 0.065(2) 0.0002(14) -0.0128(15) -0.0108(14) O1 0.0774(15) 0.0464(11) 0.132(2) -0.0009(11) -0.0513(13) -0.0152(11) C2 0.0573(19) 0.0414(15) 0.066(2) -0.0032(13) -0.0206(16) -0.0067(14) C18 0.0477(17) 0.0517(15) 0.061(2) 0.0032(14) -0.0236(15) -0.0115(13) C13 0.0524(19) 0.0458(15) 0.072(2) 0.0016(14) -0.0212(16) -0.0194(14) C1 0.0510(19) 0.0468(16) 0.066(2) -0.0014(14) -0.0141(16) 0.0008(14) C16 0.0453(17) 0.0535(15) 0.062(2) 0.0046(14) -0.0166(15) -0.0144(13) C10 0.0441(18) 0.0524(16) 0.075(2) -0.0029(14) -0.0241(16) -0.0135(14) N1 0.0488(15) 0.0532(13) 0.0590(17) -0.0003(11) -0.0179(12) -0.0092(11) N2 0.0484(15) 0.0464(12) 0.0615(17) -0.0042(11) -0.0177(12) -0.0132(11) C12 0.0470(18) 0.0577(17) 0.081(2) 0.0004(16) -0.0228(16) -0.0177(15) C6 0.060(2) 0.0516(15) 0.066(2) -0.0060(14) -0.0265(16) -0.0078(14) C20 0.0411(18) 0.0487(17) 0.061(2) -0.0029(14) -0.0144(15) -0.0100(14) C5 0.060(2) 0.0418(15) 0.076(2) -0.0006(14) -0.0256(17) -0.0100(14) C4 0.0499(19) 0.0473(15) 0.065(2) 0.0004(14) -0.0251(16) 0.0001(13) C8 0.0564(19) 0.0474(15) 0.057(2) -0.0031(13) -0.0220(15) -0.0072(13) C11 0.061(2) 0.0413(15) 0.072(2) 0.0001(14) -0.0236(17) -0.0162(14) C14 0.0390(17) 0.0495(16) 0.058(2) 0.0065(14) -0.0148(14) -0.0062(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C9 C13 1.372(3) . ? C9 C10 1.392(3) . ? C9 C8 1.504(3) . ? C7 C8 1.504(3) . ? C7 C6 1.513(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? O3 C20 1.187(2) . ? C19 C20 1.487(3) . ? C19 C18 1.507(3) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? O4 C20 1.315(3) . ? O4 H1B 0.81(3) . ? C3 C2 1.385(3) . ? C3 C4 1.395(3) . ? C3 C6 1.489(3) . ? O2 C14 1.312(3) . ? O2 H1A 0.91(3) . ? C15 C14 1.495(3) . ? C15 C16 1.519(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C17 C16 1.508(3) . ? C17 C18 1.512(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? O1 C14 1.191(3) . ? C2 C1 1.364(3) . ? C2 H2 0.9300 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C13 C12 1.371(3) . ? C13 H13 0.9300 . ? C1 N1 1.333(3) . ? C1 H1 0.9300 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C10 C11 1.378(3) . ? C10 H10 0.9300 . ? N1 C5 1.326(3) . ? N2 C11 1.321(3) . ? N2 C12 1.327(3) . ? C12 H12 0.9300 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C5 C4 1.366(3) . ? C5 H5 0.9300 . ? C4 H4 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C11 H11 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 C9 C10 115.9(2) . . ? C13 C9 C8 120.4(2) . . ? C10 C9 C8 123.7(2) . . ? C8 C7 C6 111.76(19) . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7B 109.3 . . ? C6 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? C20 C19 C18 117.2(2) . . ? C20 C19 H19A 108.0 . . ? C18 C19 H19A 108.0 . . ? C20 C19 H19B 108.0 . . ? C18 C19 H19B 108.0 . . ? H19A C19 H19B 107.2 . . ? C20 O4 H1B 112(2) . . ? C2 C3 C4 115.5(2) . . ? C2 C3 C6 120.6(2) . . ? C4 C3 C6 123.9(2) . . ? C14 O2 H1A 107.4(15) . . ? C14 C15 C16 116.0(2) . . ? C14 C15 H15A 108.3 . . ? C16 C15 H15A 108.3 . . ? C14 C15 H15B 108.3 . . ? C16 C15 H15B 108.3 . . ? H15A C15 H15B 107.4 . . ? C16 C17 C18 115.05(19) . . ? C16 C17 H17A 108.5 . . ? C18 C17 H17A 108.5 . . ? C16 C17 H17B 108.5 . . ? C18 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? C1 C2 C3 120.3(2) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C19 C18 C17 111.9(2) . . ? C19 C18 H18A 109.2 . . ? C17 C18 H18A 109.2 . . ? C19 C18 H18B 109.2 . . ? C17 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? C12 C13 C9 120.7(2) . . ? C12 C13 H13 119.6 . . ? C9 C13 H13 119.6 . . ? N1 C1 C2 123.7(2) . . ? N1 C1 H1 118.1 . . ? C2 C1 H1 118.1 . . ? C17 C16 C15 112.08(19) . . ? C17 C16 H16A 109.2 . . ? C15 C16 H16A 109.2 . . ? C17 C16 H16B 109.2 . . ? C15 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C11 C10 C9 119.5(2) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C5 N1 C1 116.6(2) . . ? C11 N2 C12 116.2(2) . . ? N2 C12 C13 123.6(2) . . ? N2 C12 H12 118.2 . . ? C13 C12 H12 118.2 . . ? C3 C6 C7 117.9(2) . . ? C3 C6 H6A 107.8 . . ? C7 C6 H6A 107.8 . . ? C3 C6 H6B 107.8 . . ? C7 C6 H6B 107.8 . . ? H6A C6 H6B 107.2 . . ? O3 C20 O4 122.6(2) . . ? O3 C20 C19 125.1(2) . . ? O4 C20 C19 112.3(2) . . ? N1 C5 C4 123.4(2) . . ? N1 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? C5 C4 C3 120.4(2) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C7 C8 C9 117.9(2) . . ? C7 C8 H8A 107.8 . . ? C9 C8 H8A 107.8 . . ? C7 C8 H8B 107.8 . . ? C9 C8 H8B 107.8 . . ? H8A C8 H8B 107.2 . . ? N2 C11 C10 124.1(2) . . ? N2 C11 H11 118.0 . . ? C10 C11 H11 118.0 . . ? O1 C14 O2 123.3(2) . . ? O1 C14 C15 124.8(2) . . ? O2 C14 C15 111.9(2) . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.145 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.034 # Attachment '- 1C4.CIF' data_1.C4 _database_code_depnum_ccdc_archive 'CCDC 779582' #TrackingRef '- 1C4.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 N2 O4' _chemical_formula_weight 302.32 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 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 21.121(2) _cell_length_b 4.9224(3) _cell_length_c 16.6380(10) _cell_angle_alpha 90.00 _cell_angle_beta 119.752(6) _cell_angle_gamma 90.00 _cell_volume 1501.77(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3714 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 28.98 _reflns_number_total 1728 _reflns_number_gt 1127 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1728 _refine_ls_number_parameters 104 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0733 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1136 _refine_ls_wR_factor_gt 0.1047 _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_restrained_S_all 0.954 _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 N1 N 0.14442(7) 0.4565(3) 0.25076(8) 0.0361(3) Uani 1 1 d . . . C1 C 0.21332(8) -0.2046(3) 0.49206(10) 0.0384(4) Uani 1 1 d . . . H1A H 0.2190 -0.1435 0.5507 0.046 Uiso 1 1 calc R . . H1B H 0.1811 -0.3608 0.4725 0.046 Uiso 1 1 calc R . . C2 C 0.07166(8) 0.8546(3) 0.11676(9) 0.0331(4) Uani 1 1 d . . . C3 C 0.17696(8) 0.0181(3) 0.42201(9) 0.0337(4) Uani 1 1 d . . . O1 O 0.21082(6) 0.0857(2) 0.37718(8) 0.0477(3) Uani 1 1 d . . . H1 H 0.1840(12) 0.217(5) 0.3307(15) 0.100(8) Uiso 1 1 d . . . O2 O 0.12096(6) 0.1226(2) 0.40851(8) 0.0532(4) Uani 1 1 d . . . C4 C 0.13297(8) 0.7270(3) 0.12559(10) 0.0389(4) Uani 1 1 d . . . H4 H 0.1509 0.7723 0.0863 0.047 Uiso 1 1 calc R . . C5 C 0.16749(8) 0.5318(3) 0.19300(10) 0.0388(4) Uani 1 1 d . . . H5 H 0.2089 0.4488 0.1983 0.047 Uiso 1 1 calc R . . C6 C 0.04785(8) 0.7758(3) 0.17695(10) 0.0420(4) Uani 1 1 d . . . H6 H 0.0068 0.8564 0.1737 0.050 Uiso 1 1 calc R . . C7 C 0.03087(8) 1.0635(3) 0.04314(9) 0.0396(4) Uani 1 1 d . . . H7A H 0.0642 1.1530 0.0275 0.047 Uiso 1 1 calc R . . H7B H 0.0113 1.2001 0.0669 0.047 Uiso 1 1 calc R . . C8 C 0.08511(9) 0.5775(3) 0.24178(10) 0.0418(4) Uani 1 1 d . . . H8 H 0.0679 0.5258 0.2812 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0348(7) 0.0387(7) 0.0312(6) 0.0091(6) 0.0137(6) 0.0042(6) C1 0.0406(9) 0.0391(9) 0.0400(8) 0.0130(7) 0.0234(7) 0.0082(7) C2 0.0331(8) 0.0300(8) 0.0266(7) 0.0027(6) 0.0077(6) -0.0019(6) C3 0.0335(8) 0.0338(8) 0.0329(8) 0.0045(7) 0.0157(7) 0.0020(7) O1 0.0429(7) 0.0563(8) 0.0508(7) 0.0295(6) 0.0284(6) 0.0179(6) O2 0.0486(7) 0.0610(8) 0.0586(7) 0.0227(6) 0.0332(6) 0.0229(6) C4 0.0393(9) 0.0424(9) 0.0368(8) 0.0083(7) 0.0203(7) -0.0005(7) C5 0.0341(9) 0.0401(9) 0.0425(8) 0.0096(7) 0.0193(7) 0.0071(7) C6 0.0374(9) 0.0491(10) 0.0391(8) 0.0091(8) 0.0186(7) 0.0115(7) C7 0.0416(9) 0.0327(9) 0.0325(8) 0.0075(7) 0.0094(7) 0.0009(7) C8 0.0430(9) 0.0518(11) 0.0364(8) 0.0125(7) 0.0241(7) 0.0085(8) _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 C8 1.3270(19) . ? N1 C5 1.3278(17) . ? C1 C1 1.505(3) 7_546 ? C1 C3 1.504(2) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C4 1.380(2) . ? C2 C6 1.3807(19) . ? C2 C7 1.5011(19) . ? C3 O2 1.2043(16) . ? C3 O1 1.3069(16) . ? O1 H1 0.95(2) . ? C4 C5 1.379(2) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C8 1.376(2) . ? C6 H6 0.9300 . ? C7 C7 1.515(3) 5_575 ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8 0.9300 . ? 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 C8 N1 C5 117.29(13) . . ? C1 C1 C3 115.97(15) 7_546 . ? C1 C1 H1A 108.3 7_546 . ? C3 C1 H1A 108.3 . . ? C1 C1 H1B 108.3 7_546 . ? C3 C1 H1B 108.3 . . ? H1A C1 H1B 107.4 . . ? C4 C2 C6 117.08(13) . . ? C4 C2 C7 121.81(13) . . ? C6 C2 C7 121.08(14) . . ? O2 C3 O1 123.34(13) . . ? O2 C3 C1 122.18(13) . . ? O1 C3 C1 114.47(12) . . ? C3 O1 H1 111.3(12) . . ? C5 C4 C2 119.56(13) . . ? C5 C4 H4 120.2 . . ? C2 C4 H4 120.2 . . ? N1 C5 C4 123.18(14) . . ? N1 C5 H5 118.4 . . ? C4 C5 H5 118.4 . . ? C8 C6 C2 119.70(14) . . ? C8 C6 H6 120.1 . . ? C2 C6 H6 120.1 . . ? C2 C7 C7 111.46(15) . 5_575 ? C2 C7 H7A 109.3 . . ? C7 C7 H7A 109.3 5_575 . ? C2 C7 H7B 109.3 . . ? C7 C7 H7B 109.3 5_575 . ? H7A C7 H7B 108.0 . . ? N1 C8 C6 123.19(14) . . ? N1 C8 H8 118.4 . . ? C6 C8 H8 118.4 . . ? _diffrn_measured_fraction_theta_max 0.864 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.192 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.040 # Attachment '- 1C5.CIF' data_1.C5 _database_code_depnum_ccdc_archive 'CCDC 779583' #TrackingRef '- 1C5.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H20 N2 O4' _chemical_formula_weight 316.35 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 P21/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 12.2889(4) _cell_length_b 11.1400(5) _cell_length_c 24.3450(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.933(4) _cell_angle_gamma 90.00 _cell_volume 3308.4(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.270 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18988 _diffrn_reflns_av_R_equivalents 0.0468 _diffrn_reflns_av_sigmaI/netI 0.1367 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 27.99 _reflns_number_total 7286 _reflns_number_gt 2091 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0803P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7286 _refine_ls_number_parameters 427 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.2850 _refine_ls_R_factor_gt 0.0827 _refine_ls_wR_factor_ref 0.2049 _refine_ls_wR_factor_gt 0.1553 _refine_ls_goodness_of_fit_ref 0.900 _refine_ls_restrained_S_all 0.006 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0949(2) 0.1136(3) 0.29326(12) 0.0793(10) Uani 1 1 d . . . H1 H 0.015(4) 0.137(4) 0.2700(18) 0.119 Uiso 1 1 d . . . O2 O 0.9976(3) 0.8385(3) 0.57433(14) 0.0950(11) Uani 1 1 d . . . O3 O 1.3870(2) 1.1433(3) 0.72207(13) 0.0864(10) Uani 1 1 d . . . H3 H 1.467(4) 1.122(4) 0.7441(18) 0.130 Uiso 1 1 d . . . O4 O 0.6026(2) 0.2555(3) 0.45371(14) 0.0853(11) Uani 1 1 d . . . H4 H 0.645(4) 0.291(5) 0.470(2) 0.128 Uiso 1 1 d . . . O5 O 1.3829(2) 0.9592(3) 0.68903(13) 0.0924(11) Uani 1 1 d . . . O6 O 0.1340(2) 0.3068(3) 0.29784(14) 0.0996(12) Uani 1 1 d . . . O7 O 0.8937(3) 0.9972(3) 0.55080(15) 0.0969(12) Uani 1 1 d . . . H7 H 0.849(4) 0.953(5) 0.526(2) 0.145 Uiso 1 1 d . . . O8 O 0.5030(2) 0.4150(3) 0.42561(13) 0.0938(11) Uani 1 1 d . . . N1 N 0.4224(3) 0.9131(4) 0.22282(14) 0.0709(11) Uani 1 1 d . . . N2 N -0.2354(3) 1.1304(3) 0.01441(14) 0.0673(10) Uani 1 1 d . . . N3 N 0.0892(3) 0.6744(3) 0.26858(13) 0.0638(10) Uani 1 1 d . . . N4 N 0.7361(3) 0.8728(4) 0.49262(14) 0.0706(10) Uani 1 1 d . . . C1 C 1.0593(3) 1.0353(4) 0.60390(17) 0.0708(13) Uani 1 1 d . . . H1A H 1.0204 1.0795 0.6298 0.085 Uiso 1 1 calc R . . H1B H 1.0784 1.0919 0.5763 0.085 Uiso 1 1 calc R . . C2 C 0.3759(4) 0.8005(5) 0.3689(3) 0.164(3) Uani 1 1 d D . . H2A H 0.4139 0.8520 0.3453 0.196 Uiso 1 1 calc R . . H2B H 0.3492 0.8520 0.3965 0.196 Uiso 1 1 calc R . . C3 C 0.1575(3) 0.2051(4) 0.30957(18) 0.0658(12) Uani 1 1 d . . . C4 C 0.5497(3) 0.7806(4) 0.43025(17) 0.0695(13) Uani 1 1 d . . . C5 C 0.4412(3) 0.2184(3) 0.39645(16) 0.0604(11) Uani 1 1 d . . . H5A H 0.4199 0.1618 0.4235 0.072 Uiso 1 1 calc R . . H5B H 0.4813 0.1739 0.3712 0.072 Uiso 1 1 calc R . . C6 C 1.3400(3) 1.0560(5) 0.69250(18) 0.0619(12) Uani 1 1 d . . . C7 C 0.3385(3) 0.2678(3) 0.36420(16) 0.0637(12) Uani 1 1 d . . . H7A H 0.3019 0.3207 0.3877 0.076 Uiso 1 1 calc R . . H7B H 0.3579 0.3144 0.3331 0.076 Uiso 1 1 calc R . . C8 C 0.9828(4) 0.9440(5) 0.57555(19) 0.0699(13) Uani 1 1 d . . . C9 C 0.2617(3) 0.1676(3) 0.34317(16) 0.0645(12) Uani 1 1 d . . . H9A H 0.3006 0.1140 0.3209 0.077 Uiso 1 1 calc R . . H9B H 0.2433 0.1221 0.3747 0.077 Uiso 1 1 calc R . . C10 C 1.1640(3) 0.9869(3) 0.63485(16) 0.0640(12) Uani 1 1 d . . . H10A H 1.2066 0.9468 0.6093 0.077 Uiso 1 1 calc R . . H10B H 1.1469 0.9288 0.6622 0.077 Uiso 1 1 calc R . . C11 C 0.5625(3) 0.9017(4) 0.44096(18) 0.0741(14) Uani 1 1 d . . . H11 H 0.5075 0.9552 0.4276 0.089 Uiso 1 1 calc R . . C12 C 0.5175(3) 0.3094(4) 0.42623(18) 0.0617(12) Uani 1 1 d . . . C13 C 1.2305(3) 1.0896(4) 0.66336(16) 0.0654(12) Uani 1 1 d . . . H13A H 1.2410 1.1501 0.6358 0.078 Uiso 1 1 calc R . . H13B H 1.1879 1.1260 0.6900 0.078 Uiso 1 1 calc R . . C14 C 0.1689(3) 0.5985(4) 0.28591(16) 0.0686(13) Uani 1 1 d . . . H14 H 0.1603 0.5180 0.2763 0.082 Uiso 1 1 calc R . . C15 C 0.2641(3) 0.6337(4) 0.31753(17) 0.0758(14) Uani 1 1 d . . . H15 H 0.3193 0.5782 0.3279 0.091 Uiso 1 1 calc R . . C16 C 0.6324(3) 0.7084(4) 0.45187(16) 0.0690(13) Uani 1 1 d . . . H16 H 0.6280 0.6260 0.4460 0.083 Uiso 1 1 calc R . . C17 C 0.1026(3) 0.7869(4) 0.28474(18) 0.0768(14) Uani 1 1 d . . . H17 H 0.0470 0.8413 0.2735 0.092 Uiso 1 1 calc R . . C18 C 0.2768(4) 0.7521(4) 0.33362(19) 0.0838(15) Uani 1 1 d . . . C19 C 0.1930(4) 0.8279(4) 0.3168(2) 0.0955(17) Uani 1 1 d . . . H19 H 0.1974 0.9082 0.3273 0.115 Uiso 1 1 calc R . . C20 C 0.7225(3) 0.7566(4) 0.48234(18) 0.0694(13) Uani 1 1 d . . . H20 H 0.7778 0.7045 0.4968 0.083 Uiso 1 1 calc R . . C21 C 0.6564(3) 0.9436(4) 0.47129(17) 0.0708(13) Uani 1 1 d . . . H21 H 0.6639 1.0259 0.4770 0.085 Uiso 1 1 calc R . . C22 C 0.4524(4) 0.7279(4) 0.3961(2) 0.112(2) Uani 1 1 d D . . H22A H 0.4795 0.6759 0.3688 0.135 Uiso 1 1 calc R . . H22B H 0.4153 0.6768 0.4203 0.135 Uiso 1 1 calc R . . C23 C 0.3903(4) 1.0262(4) 0.21981(18) 0.0770(14) Uani 1 1 d . . . H23 H 0.4380 1.0845 0.2359 0.092 Uiso 1 1 calc R . . C24 C 0.2915(4) 1.0618(4) 0.1945(2) 0.0994(17) Uani 1 1 d . . . H24 H 0.2714 1.1423 0.1947 0.119 Uiso 1 1 calc R . . C25 C 0.3543(4) 0.8318(4) 0.19847(19) 0.0785(14) Uani 1 1 d . . . H25 H 0.3756 0.7516 0.2005 0.094 Uiso 1 1 calc R . . C26 C -0.0374(4) 1.0563(6) 0.0711(2) 0.0995(19) Uani 1 1 d . . . C27 C 0.2209(4) 0.9775(6) 0.1684(2) 0.1052(19) Uani 1 1 d . . . C28 C -0.0447(4) 1.1571(5) 0.0389(3) 0.1063(19) Uani 1 1 d . . . H28 H 0.0175 1.2029 0.0358 0.128 Uiso 1 1 calc R . . C29 C -0.2274(3) 1.0336(4) 0.04578(17) 0.0660(12) Uani 1 1 d . . . H29 H -0.2905 0.9889 0.0484 0.079 Uiso 1 1 calc R . . C30 C 0.2552(4) 0.8597(5) 0.1708(2) 0.0962(17) Uani 1 1 d . . . H30 H 0.2107 0.7998 0.1535 0.115 Uiso 1 1 calc R . . C31 C -0.1321(4) 0.9960(4) 0.07439(18) 0.0846(15) Uani 1 1 d . . . H31 H -0.1317 0.9280 0.0965 0.102 Uiso 1 1 calc R . . C32 C -0.1437(4) 1.1904(4) 0.0113(2) 0.0899(16) Uani 1 1 d . . . H32 H -0.1466 1.2587 -0.0108 0.108 Uiso 1 1 calc R . . C33 C 0.0974(5) 1.0135(7) 0.1473(3) 0.178(3) Uani 1 1 d D . . H33A H 0.0480 0.9582 0.1626 0.214 Uiso 1 1 calc R . . H33B H 0.0828 1.0935 0.1604 0.214 Uiso 1 1 calc R . . C34 C 0.0789(5) 1.0112(8) 0.0937(3) 0.184(3) Uani 1 1 d D . . H34A H 0.0878 0.9297 0.0810 0.221 Uiso 1 1 calc R . . H34B H 0.1330 1.0609 0.0786 0.221 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 0.074(2) 0.058(2) 0.096(2) -0.0075(18) -0.0296(17) 0.0068(17) O2 0.096(2) 0.070(2) 0.116(3) -0.027(2) -0.0021(19) -0.010(2) O3 0.0695(19) 0.069(2) 0.111(3) -0.013(2) -0.0283(18) 0.0050(18) O4 0.067(2) 0.077(2) 0.104(3) -0.009(2) -0.0238(18) -0.0038(18) O5 0.088(2) 0.065(2) 0.117(3) -0.009(2) -0.0171(19) 0.013(2) O6 0.084(2) 0.058(2) 0.145(3) 0.018(2) -0.0326(19) 0.001(2) O7 0.076(2) 0.090(3) 0.115(3) -0.013(2) -0.028(2) -0.015(2) O8 0.092(2) 0.054(2) 0.128(3) -0.017(2) -0.0178(19) 0.002(2) N1 0.058(2) 0.071(3) 0.080(3) 0.002(2) -0.0090(19) 0.005(2) N2 0.055(2) 0.067(3) 0.076(3) 0.008(2) -0.0039(19) -0.001(2) N3 0.063(2) 0.061(3) 0.064(2) -0.003(2) -0.0067(18) -0.008(2) N4 0.060(2) 0.076(3) 0.073(3) -0.004(2) -0.0058(19) -0.010(2) C1 0.062(3) 0.071(3) 0.078(3) -0.015(3) 0.002(2) -0.009(3) C2 0.134(5) 0.097(5) 0.228(7) 0.035(5) -0.112(5) -0.035(4) C3 0.066(3) 0.060(3) 0.067(3) -0.002(3) -0.009(2) 0.004(3) C4 0.058(3) 0.067(3) 0.078(3) 0.006(3) -0.014(2) -0.010(3) C5 0.061(2) 0.053(3) 0.066(3) -0.012(2) 0.002(2) 0.001(2) C6 0.055(3) 0.064(4) 0.066(3) 0.006(3) 0.006(2) -0.007(3) C7 0.060(2) 0.056(3) 0.071(3) -0.001(2) -0.008(2) 0.003(2) C8 0.060(3) 0.077(4) 0.071(3) -0.014(3) 0.005(2) -0.017(3) C9 0.065(2) 0.050(3) 0.074(3) -0.001(2) -0.011(2) 0.003(2) C10 0.063(3) 0.063(3) 0.064(3) 0.000(2) 0.000(2) -0.006(2) C11 0.061(3) 0.066(3) 0.089(4) 0.008(3) -0.016(2) 0.003(3) C12 0.058(3) 0.063(3) 0.064(3) -0.006(3) 0.007(2) 0.003(3) C13 0.059(3) 0.063(3) 0.071(3) 0.002(2) -0.006(2) 0.003(2) C14 0.078(3) 0.051(3) 0.072(3) 0.000(2) -0.011(3) -0.003(3) C15 0.066(3) 0.075(4) 0.080(3) 0.010(3) -0.017(2) 0.003(3) C16 0.066(3) 0.063(3) 0.073(3) 0.011(3) -0.009(2) -0.005(3) C17 0.066(3) 0.067(3) 0.091(4) -0.008(3) -0.018(3) 0.006(3) C18 0.076(3) 0.063(3) 0.101(4) 0.007(3) -0.037(3) -0.020(3) C19 0.098(4) 0.052(3) 0.123(4) -0.006(3) -0.042(3) -0.007(3) C20 0.059(3) 0.076(4) 0.072(3) 0.013(3) 0.001(2) 0.010(3) C21 0.070(3) 0.055(3) 0.085(3) -0.001(3) -0.002(3) -0.009(3) C22 0.090(3) 0.069(4) 0.160(5) 0.019(4) -0.054(4) -0.018(3) C23 0.077(3) 0.062(3) 0.085(4) 0.004(3) -0.017(3) -0.005(3) C24 0.110(4) 0.071(4) 0.108(4) 0.002(3) -0.025(3) 0.028(4) C25 0.073(3) 0.062(3) 0.095(4) -0.003(3) -0.010(3) 0.009(3) C26 0.055(3) 0.117(5) 0.115(5) 0.000(4) -0.036(3) 0.011(3) C27 0.076(4) 0.115(5) 0.112(4) -0.002(4) -0.039(3) 0.034(4) C28 0.053(3) 0.087(4) 0.175(6) -0.002(4) -0.002(3) -0.013(3) C29 0.057(3) 0.070(3) 0.069(3) 0.007(3) 0.001(2) -0.013(3) C30 0.076(3) 0.085(4) 0.118(4) -0.013(4) -0.026(3) 0.000(3) C31 0.071(3) 0.094(4) 0.085(4) 0.027(3) -0.009(3) 0.007(3) C32 0.073(3) 0.073(4) 0.122(4) 0.019(3) 0.007(3) 0.003(3) C33 0.164(6) 0.223(9) 0.136(6) -0.004(7) -0.027(5) 0.059(6) C34 0.153(6) 0.253(9) 0.132(6) -0.004(7) -0.047(5) 0.032(6) _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 1.310(5) . ? O1 H1 1.10(4) . ? O2 C8 1.190(5) . ? O3 C6 1.302(5) . ? O3 H3 1.09(5) . ? O4 C12 1.316(5) . ? O4 H4 0.74(5) . ? O5 C6 1.208(5) . ? O6 C3 1.195(4) . ? O7 C8 1.324(5) . ? O7 H7 0.91(5) . ? O8 C12 1.190(4) . ? N1 C25 1.324(5) . ? N1 C23 1.319(5) . ? N2 C29 1.318(4) . ? N2 C32 1.320(5) . ? N3 C17 1.318(5) . ? N3 C14 1.323(5) . ? N4 C21 1.315(5) . ? N4 C20 1.325(5) . ? C1 C8 1.496(5) . ? C1 C10 1.511(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C22 1.352(5) . ? C2 C18 1.504(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C9 1.494(5) . ? C4 C16 1.352(5) . ? C4 C11 1.380(5) . ? C4 C22 1.492(5) . ? C5 C12 1.507(5) . ? C5 C7 1.507(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C13 1.492(5) . ? C7 C9 1.511(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C13 1.524(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C21 1.374(5) . ? C11 H11 0.9300 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.377(5) . ? C14 H14 0.9300 . ? C15 C18 1.378(5) . ? C15 H15 0.9300 . ? C16 C20 1.365(5) . ? C16 H16 0.9300 . ? C17 C19 1.357(5) . ? C17 H17 0.9300 . ? C18 C19 1.357(6) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.352(6) . ? C23 H23 0.9300 . ? C24 C27 1.381(6) . ? C24 H24 0.9300 . ? C25 C30 1.356(5) . ? C25 H25 0.9300 . ? C26 C31 1.354(6) . ? C26 C28 1.366(7) . ? C26 C34 1.551(7) . ? C27 C30 1.377(6) . ? C27 C33 1.594(7) . ? C28 C32 1.369(6) . ? C28 H28 0.9300 . ? C29 C31 1.355(5) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? C33 C34 1.299(6) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? 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 H1 115(2) . . ? C6 O3 H3 115(2) . . ? C12 O4 H4 120(4) . . ? C8 O7 H7 117(3) . . ? C25 N1 C23 117.4(4) . . ? C29 N2 C32 116.3(4) . . ? C17 N3 C14 116.8(3) . . ? C21 N4 C20 116.1(4) . . ? C8 C1 C10 115.9(4) . . ? C8 C1 H1A 108.3 . . ? C10 C1 H1A 108.3 . . ? C8 C1 H1B 108.3 . . ? C10 C1 H1B 108.3 . . ? H1A C1 H1B 107.4 . . ? C22 C2 C18 122.2(5) . . ? C22 C2 H2A 106.8 . . ? C18 C2 H2A 106.8 . . ? C22 C2 H2B 106.8 . . ? C18 C2 H2B 106.8 . . ? H2A C2 H2B 106.6 . . ? O6 C3 O1 123.3(4) . . ? O6 C3 C9 124.3(4) . . ? O1 C3 C9 112.4(4) . . ? C16 C4 C11 116.4(4) . . ? C16 C4 C22 119.8(4) . . ? C11 C4 C22 123.8(4) . . ? C12 C5 C7 116.0(3) . . ? C12 C5 H5A 108.3 . . ? C7 C5 H5A 108.3 . . ? C12 C5 H5B 108.3 . . ? C7 C5 H5B 108.3 . . ? H5A C5 H5B 107.4 . . ? O5 C6 O3 122.5(4) . . ? O5 C6 C13 124.6(4) . . ? O3 C6 C13 112.9(4) . . ? C9 C7 C5 110.9(3) . . ? C9 C7 H7A 109.5 . . ? C5 C7 H7A 109.5 . . ? C9 C7 H7B 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? O2 C8 O7 123.4(4) . . ? O2 C8 C1 126.4(5) . . ? O7 C8 C1 110.1(4) . . ? C3 C9 C7 116.0(3) . . ? C3 C9 H9A 108.3 . . ? C7 C9 H9A 108.3 . . ? C3 C9 H9B 108.3 . . ? C7 C9 H9B 108.3 . . ? H9A C9 H9B 107.4 . . ? C1 C10 C13 109.7(3) . . ? C1 C10 H10A 109.7 . . ? C13 C10 H10A 109.7 . . ? C1 C10 H10B 109.7 . . ? C13 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? C21 C11 C4 120.2(4) . . ? C21 C11 H11 119.9 . . ? C4 C11 H11 119.9 . . ? O8 C12 O4 124.5(4) . . ? O8 C12 C5 125.2(4) . . ? O4 C12 C5 110.4(4) . . ? C6 C13 C10 115.6(3) . . ? C6 C13 H13A 108.4 . . ? C10 C13 H13A 108.4 . . ? C6 C13 H13B 108.4 . . ? C10 C13 H13B 108.4 . . ? H13A C13 H13B 107.5 . . ? N3 C14 C15 122.8(4) . . ? N3 C14 H14 118.6 . . ? C15 C14 H14 118.6 . . ? C14 C15 C18 119.4(4) . . ? C14 C15 H15 120.3 . . ? C18 C15 H15 120.3 . . ? C4 C16 C20 120.0(4) . . ? C4 C16 H16 120.0 . . ? C20 C16 H16 120.0 . . ? N3 C17 C19 123.8(4) . . ? N3 C17 H17 118.1 . . ? C19 C17 H17 118.1 . . ? C19 C18 C15 117.0(4) . . ? C19 C18 C2 118.8(5) . . ? C15 C18 C2 124.2(4) . . ? C17 C19 C18 120.2(4) . . ? C17 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? N4 C20 C16 124.2(4) . . ? N4 C20 H20 117.9 . . ? C16 C20 H20 117.9 . . ? N4 C21 C11 123.1(4) . . ? N4 C21 H21 118.5 . . ? C11 C21 H21 118.5 . . ? C2 C22 C4 120.0(4) . . ? C2 C22 H22A 107.3 . . ? C4 C22 H22A 107.3 . . ? C2 C22 H22B 107.3 . . ? C4 C22 H22B 107.3 . . ? H22A C22 H22B 106.9 . . ? N1 C23 C24 123.5(4) . . ? N1 C23 H23 118.3 . . ? C24 C23 H23 118.3 . . ? C23 C24 C27 119.3(4) . . ? C23 C24 H24 120.4 . . ? C27 C24 H24 120.4 . . ? N1 C25 C30 123.1(4) . . ? N1 C25 H25 118.4 . . ? C30 C25 H25 118.4 . . ? C31 C26 C28 116.4(4) . . ? C31 C26 C34 125.5(6) . . ? C28 C26 C34 117.5(6) . . ? C24 C27 C30 117.2(4) . . ? C24 C27 C33 119.9(6) . . ? C30 C27 C33 121.9(6) . . ? C26 C28 C32 119.8(5) . . ? C26 C28 H28 120.1 . . ? C32 C28 H28 120.1 . . ? N2 C29 C31 123.4(4) . . ? N2 C29 H29 118.3 . . ? C31 C29 H29 118.3 . . ? C25 C30 C27 119.4(5) . . ? C25 C30 H30 120.3 . . ? C27 C30 H30 120.3 . . ? C29 C31 C26 120.8(5) . . ? C29 C31 H31 119.6 . . ? C26 C31 H31 119.6 . . ? N2 C32 C28 123.3(5) . . ? N2 C32 H32 118.4 . . ? C28 C32 H32 118.4 . . ? C34 C33 C27 111.3(6) . . ? C34 C33 H33A 109.4 . . ? C27 C33 H33A 109.4 . . ? C34 C33 H33B 109.4 . . ? C27 C33 H33B 109.4 . . ? H33A C33 H33B 108.0 . . ? C33 C34 C26 113.0(6) . . ? C33 C34 H34A 109.0 . . ? C26 C34 H34A 109.0 . . ? C33 C34 H34B 109.0 . . ? C26 C34 H34B 109.0 . . ? H34A C34 H34B 107.8 . . ? _diffrn_measured_fraction_theta_max 0.913 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.354 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.038 # Attachment '- 1C6.CIF' data_1.C6 _database_code_depnum_ccdc_archive 'CCDC 779584' #TrackingRef '- 1C6.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 N2 O4' _chemical_formula_weight 330.38 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 7.2159(6) _cell_length_b 7.3354(7) _cell_length_c 8.8449(7) _cell_angle_alpha 90.210(7) _cell_angle_beta 93.428(6) _cell_angle_gamma 115.808(9) _cell_volume 420.49(6) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 176 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4004 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 28.91 _reflns_number_total 1907 _reflns_number_gt 1197 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0847P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1907 _refine_ls_number_parameters 112 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0874 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1370 _refine_ls_wR_factor_gt 0.1240 _refine_ls_goodness_of_fit_ref 0.916 _refine_ls_restrained_S_all 0.916 _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 C1 C 0.0683(2) 0.2245(2) 0.63352(18) 0.0435(4) Uani 1 1 d . . . O1 O -0.12602(19) 0.1782(2) 0.59817(15) 0.0665(4) Uani 1 1 d . . . H10 H -0.214(4) 0.096(4) 0.665(3) 0.100 Uiso 1 1 d . . . O2 O 0.1257(2) 0.1717(2) 0.74792(15) 0.0728(5) Uani 1 1 d . . . C2 C 0.2070(2) 0.3510(3) 0.51668(17) 0.0448(4) Uani 1 1 d . . . H2A H 0.1760 0.4651 0.4967 0.054 Uiso 1 1 calc R . . H2B H 0.1750 0.2703 0.4233 0.054 Uiso 1 1 calc R . . C3 C 0.4350(2) 0.4310(3) 0.55885(18) 0.0433(4) Uani 1 1 d . . . H3A H 0.4697 0.3179 0.5708 0.052 Uiso 1 1 calc R . . H3B H 0.4672 0.5050 0.6554 0.052 Uiso 1 1 calc R . . C4 C 0.8926(3) 0.4758(3) -0.0278(2) 0.0534(5) Uani 1 1 d . . . H4A H 0.8706 0.4198 -0.1304 0.064 Uiso 1 1 calc R . . H4B H 0.8793 0.6017 -0.0329 0.064 Uiso 1 1 calc R . . C5 C 0.7223(2) 0.3309(2) 0.06303(17) 0.0404(4) Uani 1 1 d . . . C6 C 0.7572(3) 0.2552(3) 0.19902(18) 0.0483(5) Uani 1 1 d . . . H6 H 0.8913 0.2931 0.2394 0.058 Uiso 1 1 calc R . . C7 C 0.5919(3) 0.1233(3) 0.27440(18) 0.0492(5) Uani 1 1 d . . . H7 H 0.6185 0.0731 0.3654 0.059 Uiso 1 1 calc R . . N1 N 0.3976(2) 0.0644(2) 0.22425(15) 0.0469(4) Uani 1 1 d . . . C8 C 0.3629(3) 0.1361(3) 0.09280(19) 0.0454(4) Uani 1 1 d . . . H8 H 0.2270 0.0954 0.0554 0.054 Uiso 1 1 calc R . . C9 C 0.5185(3) 0.2673(3) 0.01008(18) 0.0436(4) Uani 1 1 d . . . H9 H 0.4871 0.3134 -0.0812 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0327(10) 0.0446(10) 0.0468(9) 0.0074(7) 0.0062(7) 0.0106(8) O1 0.0298(7) 0.0910(11) 0.0633(8) 0.0331(7) 0.0082(6) 0.0111(7) O2 0.0441(8) 0.0993(11) 0.0660(8) 0.0414(7) 0.0076(6) 0.0219(8) C2 0.0365(10) 0.0480(10) 0.0444(9) 0.0124(7) 0.0084(7) 0.0124(8) C3 0.0332(9) 0.0449(10) 0.0473(9) 0.0107(7) 0.0078(7) 0.0121(8) C4 0.0388(10) 0.0615(12) 0.0530(10) 0.0184(8) 0.0114(8) 0.0143(9) C5 0.0335(10) 0.0418(10) 0.0418(8) 0.0064(7) 0.0077(7) 0.0118(8) C6 0.0314(9) 0.0589(11) 0.0470(10) 0.0098(8) 0.0014(7) 0.0126(8) C7 0.0400(11) 0.0554(11) 0.0432(9) 0.0126(7) 0.0054(7) 0.0119(9) N1 0.0351(8) 0.0473(9) 0.0504(8) 0.0062(6) 0.0096(6) 0.0099(6) C8 0.0316(9) 0.0456(10) 0.0546(10) 0.0028(8) 0.0028(7) 0.0128(8) C9 0.0378(10) 0.0457(10) 0.0443(9) 0.0079(7) 0.0015(7) 0.0155(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.1989(19) . ? C1 O1 1.3083(19) . ? C1 C2 1.501(2) . ? O1 H10 0.91(3) . ? C2 C3 1.508(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C3 1.512(3) 2_666 ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C4 1.483(3) 2_765 ? C4 C5 1.507(2) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C9 1.385(2) . ? C5 C6 1.381(2) . ? C6 C7 1.378(2) . ? C6 H6 0.9300 . ? C7 N1 1.321(2) . ? C7 H7 0.9300 . ? N1 C8 1.333(2) . ? C8 C9 1.373(2) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? 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 O2 C1 O1 122.68(16) . . ? O2 C1 C2 124.88(16) . . ? O1 C1 C2 112.43(15) . . ? C1 O1 H10 114.0(16) . . ? C1 C2 C3 115.26(14) . . ? C1 C2 H2A 108.5 . . ? C3 C2 H2A 108.5 . . ? C1 C2 H2B 108.5 . . ? C3 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? C2 C3 C3 112.34(17) . 2_666 ? C2 C3 H3A 109.1 . . ? C3 C3 H3A 109.1 2_666 . ? C2 C3 H3B 109.1 . . ? C3 C3 H3B 109.1 2_666 . ? H3A C3 H3B 107.9 . . ? C4 C4 C5 117.08(19) 2_765 . ? C4 C4 H4A 108.0 2_765 . ? C5 C4 H4A 108.0 . . ? C4 C4 H4B 108.0 2_765 . ? C5 C4 H4B 108.0 . . ? H4A C4 H4B 107.3 . . ? C9 C5 C6 116.87(15) . . ? C9 C5 C4 119.63(15) . . ? C6 C5 C4 123.50(15) . . ? C7 C6 C5 119.54(16) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? N1 C7 C6 123.44(16) . . ? N1 C7 H7 118.3 . . ? C6 C7 H7 118.3 . . ? C7 N1 C8 117.35(14) . . ? N1 C8 C9 122.97(16) . . ? N1 C8 H8 118.5 . . ? C9 C8 H8 118.5 . . ? C8 C9 C5 119.83(15) . . ? C8 C9 H9 120.1 . . ? C5 C9 H9 120.1 . . ? _diffrn_measured_fraction_theta_max 0.862 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.189 _refine_diff_density_min -0.139 _refine_diff_density_rms 0.034 # Attachment '- 1C7.CIF' data_1.C7 _database_code_depnum_ccdc_archive 'CCDC 779585' #TrackingRef '- 1C7.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H24 N2 O4' _chemical_formula_weight 344.40 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 P21/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 11.1380(10) _cell_length_b 47.332(5) _cell_length_c 14.436(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.8320(10) _cell_angle_gamma 90.00 _cell_volume 7321.7(14) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2944 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 60898 _diffrn_reflns_av_R_equivalents 0.0787 _diffrn_reflns_av_sigmaI/netI 0.0718 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -62 _diffrn_reflns_limit_k_max 61 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 0.86 _diffrn_reflns_theta_max 28.16 _reflns_number_total 16573 _reflns_number_gt 6574 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1455P)^2^+1.8531P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00021(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 16573 _refine_ls_number_parameters 934 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1923 _refine_ls_R_factor_gt 0.0827 _refine_ls_wR_factor_ref 0.2987 _refine_ls_wR_factor_gt 0.2294 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group H4O H 0.618(3) -0.1312(7) 0.221(2) 0.055(9) Uiso 1 1 d . . . H3O H -0.133(3) 0.3569(8) 0.274(2) 0.070(11) Uiso 1 1 d . . . H17O H 0.088(4) 0.2428(9) 0.030(3) 0.109(16) Uiso 1 1 d . . . H10O H 0.491(4) 0.1109(9) 0.257(3) 0.090(13) Uiso 1 1 d . . . H11O H -0.399(5) 0.2438(11) 0.534(4) 0.14(2) Uiso 1 1 d . . . H1O H -0.098(5) 0.1171(12) 0.280(4) 0.15(2) Uiso 1 1 d . . . H6O H -0.294(4) 0.0037(10) 0.518(3) 0.121(17) Uiso 1 1 d . . . H18O H 0.210(5) 0.0033(11) 0.007(3) 0.15(2) Uiso 1 1 d . . . N1 N -0.0502(3) 0.08445(6) 0.2745(2) 0.0590(8) Uani 1 1 d . . . N2 N 0.3888(3) 0.33935(6) 0.2629(2) 0.0597(8) Uani 1 1 d . . . N3 N 0.0943(3) -0.10941(6) 0.2281(2) 0.0603(8) Uani 1 1 d . . . N4 N 0.4539(3) 0.14294(6) 0.2627(2) 0.0634(8) Uani 1 1 d . . . N5 N -0.3705(3) 0.27725(6) 0.5214(2) 0.0592(8) Uani 1 1 d . . . N6 N -0.2491(3) 0.47131(6) 0.5021(2) 0.0631(8) Uani 1 1 d . . . O1 O -0.1257(3) 0.13583(6) 0.2933(2) 0.0748(8) Uani 1 1 d . . . O2 O 0.0362(3) 0.15311(6) 0.2524(2) 0.0886(9) Uani 1 1 d . . . O3 O -0.1684(3) 0.33785(6) 0.2810(2) 0.0766(8) Uani 1 1 d . . . O4 O 0.6514(3) -0.10680(6) 0.2299(2) 0.0853(9) Uani 1 1 d . . . O5 O 0.4726(3) -0.09908(6) 0.2621(2) 0.0918(10) Uani 1 1 d . . . O6 O -0.3409(3) 0.02280(5) 0.5219(2) 0.0802(9) Uani 1 1 d . . . O7 O 0.0082(3) 0.32388(6) 0.2565(3) 0.0939(10) Uani 1 1 d . . . O8 O -0.1720(3) 0.04159(5) 0.4979(2) 0.0856(9) Uani 1 1 d . . . O9 O 0.3641(3) 0.07204(6) 0.2628(3) 0.0954(10) Uani 1 1 d . . . O10 O 0.5377(3) 0.09161(6) 0.2495(2) 0.0843(9) Uani 1 1 d . . . O11 O -0.4161(3) 0.22324(6) 0.5376(2) 0.0846(10) Uani 1 1 d . . . O16 O -0.2482(3) 0.21294(6) 0.4911(2) 0.0897(10) Uani 1 1 d . . . C1 C -0.1368(3) 0.28921(7) 0.2752(3) 0.0596(10) Uani 1 1 d . . . H1A H -0.2140 0.2873 0.2244 0.071 Uiso 1 1 calc R . . H1B H -0.1575 0.2874 0.3360 0.071 Uiso 1 1 calc R . . C2 C -0.1163(3) 0.23702(7) 0.2760(3) 0.0593(10) Uani 1 1 d . . . H2A H -0.1339 0.2366 0.3383 0.071 Uiso 1 1 calc R . . H2B H -0.1958 0.2365 0.2272 0.071 Uiso 1 1 calc R . . C3 C 0.4677(4) 0.06968(8) 0.2544(3) 0.0583(9) Uani 1 1 d . . . C4 C -0.0452(3) 0.21051(7) 0.2667(3) 0.0566(9) Uani 1 1 d . . . H4A H 0.0335 0.2102 0.3164 0.068 Uiso 1 1 calc R . . H4B H -0.0271 0.2104 0.2046 0.068 Uiso 1 1 calc R . . C5 C -0.0614(4) 0.15680(7) 0.2725(3) 0.0559(9) Uani 1 1 d . . . C6 C -0.0533(3) 0.26477(7) 0.2670(3) 0.0563(9) Uani 1 1 d . . . H6A H 0.0247 0.2661 0.3172 0.068 Uiso 1 1 calc R . . H6B H -0.0345 0.2656 0.2052 0.068 Uiso 1 1 calc R . . C7 C 0.4067(4) 0.20040(9) 0.2682(3) 0.0809(13) Uani 1 1 d . . . C8 C 0.5974(3) -0.05995(7) 0.2405(3) 0.0611(10) Uani 1 1 d . . . H8A H 0.6144 -0.0566 0.1790 0.073 Uiso 1 1 calc R . . H8B H 0.6743 -0.0565 0.2903 0.073 Uiso 1 1 calc R . . C9 C 0.4656(3) 0.01541(7) 0.2552(3) 0.0601(10) Uani 1 1 d . . . H9A H 0.3884 0.0144 0.2040 0.072 Uiso 1 1 calc R . . H9B H 0.4457 0.0144 0.3164 0.072 Uiso 1 1 calc R . . C10 C -0.2727(3) 0.04448(7) 0.5111(3) 0.0537(9) Uani 1 1 d . . . C11 C 0.0244(4) -0.05365(8) 0.2469(3) 0.0717(11) Uani 1 1 d . . . C12 C 0.5322(4) 0.04262(7) 0.2481(3) 0.0668(11) Uani 1 1 d . . . H12A H 0.6100 0.0426 0.2988 0.080 Uiso 1 1 calc R . . H12B H 0.5536 0.0425 0.1873 0.080 Uiso 1 1 calc R . . C13 C 0.4212(4) 0.28171(9) 0.2616(4) 0.0873(14) Uani 1 1 d . . . C14 C 0.5008(3) -0.03844(7) 0.2522(3) 0.0597(10) Uani 1 1 d . . . H14A H 0.4237 -0.0410 0.2018 0.072 Uiso 1 1 calc R . . H14B H 0.4834 -0.0411 0.3138 0.072 Uiso 1 1 calc R . . C15 C -0.1205(3) 0.18463(7) 0.2759(3) 0.0576(9) Uani 1 1 d . . . H15A H -0.1424 0.1859 0.3363 0.069 Uiso 1 1 calc R . . H15B H -0.1978 0.1852 0.2246 0.069 Uiso 1 1 calc R . . C16 C -0.0180(4) -0.10280(8) 0.2390(3) 0.0643(10) Uani 1 1 d . . . H16 H -0.0734 -0.1174 0.2401 0.077 Uiso 1 1 calc R . . C17 C 0.0066(4) 0.02804(8) 0.2521(3) 0.0741(12) Uani 1 1 d . . . C18 C 0.0910(4) 0.04909(8) 0.2524(3) 0.0660(11) Uani 1 1 d . . . H18 H 0.1693 0.0446 0.2453 0.079 Uiso 1 1 calc R . . C19 C -0.3417(3) 0.12410(7) 0.5201(3) 0.0576(9) Uani 1 1 d . . . H19A H -0.4202 0.1231 0.4703 0.069 Uiso 1 1 calc R . . H19B H -0.3607 0.1228 0.5817 0.069 Uiso 1 1 calc R . . C20 C -0.1069(4) 0.03580(8) 0.2653(3) 0.0801(13) Uani 1 1 d . . . H20 H -0.1665 0.0223 0.2674 0.096 Uiso 1 1 calc R . . C21 C -0.0889(3) 0.31825(7) 0.2702(3) 0.0546(9) Uani 1 1 d . . . C22 C 0.3119(4) 0.29312(8) 0.2716(3) 0.0781(12) Uani 1 1 d . . . H22 H 0.2475 0.2815 0.2784 0.094 Uiso 1 1 calc R . . C23 C 0.5647(3) -0.08996(8) 0.2448(3) 0.0578(9) Uani 1 1 d . . . C24 C 0.3187(4) 0.18045(9) 0.2720(3) 0.0729(11) Uani 1 1 d . . . H24 H 0.2407 0.1861 0.2769 0.088 Uiso 1 1 calc R . . C25 C -0.0546(4) -0.07613(9) 0.2482(3) 0.0717(11) Uani 1 1 d . . . H25 H -0.1337 -0.0728 0.2556 0.086 Uiso 1 1 calc R . . C26 C 0.5408(4) 0.16184(8) 0.2600(3) 0.0686(11) Uani 1 1 d . . . H26 H 0.6184 0.1555 0.2567 0.082 Uiso 1 1 calc R . . C27 C -0.0194(5) -0.02455(9) 0.2617(4) 0.1106(18) Uani 1 1 d D . . H27A H -0.1065 -0.0231 0.2257 0.133 Uiso 1 1 calc R . . H27B H -0.0155 -0.0226 0.3293 0.133 Uiso 1 1 calc R . . C28 C 0.5506(3) -0.00905(7) 0.2464(3) 0.0621(10) Uani 1 1 d . . . H28A H 0.5707 -0.0072 0.1854 0.074 Uiso 1 1 calc R . . H28B H 0.6280 -0.0071 0.2970 0.074 Uiso 1 1 calc R . . C29 C 0.0439(5) -0.00174(9) 0.2360(5) 0.125(2) Uani 1 1 d D . . H29A H 0.0377 -0.0036 0.1679 0.151 Uiso 1 1 calc R . . H29B H 0.1314 -0.0038 0.2702 0.151 Uiso 1 1 calc R . . C30 C 0.1388(4) -0.06087(8) 0.2363(3) 0.0708(11) Uani 1 1 d . . . H30 H 0.1960 -0.0466 0.2352 0.085 Uiso 1 1 calc R . . C31 C -0.1298(3) 0.06403(7) 0.2751(3) 0.0641(10) Uani 1 1 d . . . H31 H -0.2073 0.0690 0.2828 0.077 Uiso 1 1 calc R . . C32 C -0.3356(3) 0.07191(7) 0.5166(3) 0.0570(9) Uani 1 1 d . . . H32A H -0.3577 0.0724 0.5772 0.068 Uiso 1 1 calc R . . H32B H -0.4129 0.0723 0.4654 0.068 Uiso 1 1 calc R . . C33 C 0.0605(4) 0.07641(8) 0.2630(3) 0.0635(10) Uani 1 1 d . . . H33 H 0.1193 0.0903 0.2624 0.076 Uiso 1 1 calc R . . C34 C -0.2625(3) 0.28695(8) 0.5133(3) 0.0635(10) Uani 1 1 d . . . H34 H -0.1985 0.2741 0.5157 0.076 Uiso 1 1 calc R . . C35 C 0.1714(4) -0.08821(8) 0.2272(3) 0.0644(10) Uani 1 1 d . . . H35 H 0.2503 -0.0921 0.2202 0.077 Uiso 1 1 calc R . . C36 C -0.3745(3) 0.17532(7) 0.5233(3) 0.0604(10) Uani 1 1 d . . . H36A H -0.4517 0.1721 0.4736 0.072 Uiso 1 1 calc R . . H36B H -0.3926 0.1728 0.5848 0.072 Uiso 1 1 calc R . . C37 C -0.2631(3) 0.09848(7) 0.5096(3) 0.0555(9) Uani 1 1 d . . . H37A H -0.2442 0.0991 0.4479 0.067 Uiso 1 1 calc R . . H37B H -0.1850 0.0986 0.5600 0.067 Uiso 1 1 calc R . . C38 C -0.3333(4) 0.33441(8) 0.4958(3) 0.0730(12) Uani 1 1 d . . . C39 C 0.2992(3) 0.32201(8) 0.2714(3) 0.0634(10) Uani 1 1 d . . . H39 H 0.2247 0.3297 0.2774 0.076 Uiso 1 1 calc R . . C40 C -0.3599(4) 0.46201(8) 0.5058(3) 0.0670(11) Uani 1 1 d . . . H40 H -0.4243 0.4750 0.4991 0.080 Uiso 1 1 calc R . . C41 C -0.3380(3) 0.20552(7) 0.5166(3) 0.0560(9) Uani 1 1 d . . . C42 C 0.3050(4) 0.07696(7) 0.4977(3) 0.0656(11) Uani 1 1 d . . . H42 H 0.3635 0.0906 0.4941 0.079 Uiso 1 1 calc R . . C43 C -0.4435(4) 0.32440(8) 0.5057(3) 0.0714(11) Uani 1 1 d . . . H43 H -0.5086 0.3369 0.5042 0.086 Uiso 1 1 calc R . . C44 C 0.3442(4) 0.15302(8) 0.2687(3) 0.0646(10) Uani 1 1 d . . . H44 H 0.2820 0.1401 0.2707 0.078 Uiso 1 1 calc R . . C45 C -0.4591(3) 0.29599(8) 0.5179(3) 0.0647(10) Uani 1 1 d . . . H45 H -0.5358 0.2897 0.5239 0.078 Uiso 1 1 calc R . . C46 C -0.2832(3) 0.15276(7) 0.5142(3) 0.0558(9) Uani 1 1 d . . . H46A H -0.2066 0.1547 0.5655 0.067 Uiso 1 1 calc R . . H46B H -0.2634 0.1546 0.4531 0.067 Uiso 1 1 calc R . . C47 C 0.3754(6) 0.23086(10) 0.2752(6) 0.143(3) Uani 1 1 d D . . H47A H 0.2928 0.2339 0.2323 0.172 Uiso 1 1 calc R . . H47B H 0.3696 0.2342 0.3401 0.172 Uiso 1 1 calc R . . C48 C -0.1603(4) 0.45256(8) 0.5109(3) 0.0688(11) Uani 1 1 d . . . H48 H -0.0820 0.4588 0.5082 0.083 Uiso 1 1 calc R . . C49 C 0.4936(4) 0.32815(8) 0.2539(3) 0.0646(10) Uani 1 1 d . . . H49 H 0.5575 0.3400 0.2479 0.078 Uiso 1 1 calc R . . C50 C 0.5211(4) 0.19017(8) 0.2620(3) 0.0785(13) Uani 1 1 d . . . H50 H 0.5843 0.2027 0.2591 0.094 Uiso 1 1 calc R . . C51 C 0.4507(6) 0.25068(11) 0.2557(6) 0.174(3) Uani 1 1 d D . . H51A H 0.4568 0.2472 0.1910 0.209 Uiso 1 1 calc R . . H51B H 0.5331 0.2475 0.2988 0.209 Uiso 1 1 calc R . . C52 C -0.2901(4) 0.41460(8) 0.5294(3) 0.0720(11) Uani 1 1 d . . . C53 C -0.2405(4) 0.31477(9) 0.5018(3) 0.0737(12) Uani 1 1 d . . . H53 H -0.1622 0.3206 0.4979 0.088 Uiso 1 1 calc R . . C54 C -0.1763(4) 0.42436(8) 0.5238(3) 0.0778(12) Uani 1 1 d . . . H54 H -0.1104 0.4119 0.5288 0.093 Uiso 1 1 calc R . . C55 C 0.5104(4) 0.30025(9) 0.2532(3) 0.0802(13) Uani 1 1 d . . . H55 H 0.5858 0.2933 0.2468 0.096 Uiso 1 1 calc R . . C56 C -0.3838(4) 0.43445(8) 0.5189(3) 0.0695(11) Uani 1 1 d . . . H56 H -0.4632 0.4289 0.5208 0.083 Uiso 1 1 calc R . . O17 O 0.0661(2) 0.22304(5) 0.0319(2) 0.0717(8) Uani 1 1 d . . . O18 O 0.1716(3) 0.02276(6) 0.0233(2) 0.0814(9) Uani 1 1 d . . . O19 O 0.2480(3) 0.21290(6) 0.0070(2) 0.0880(10) Uani 1 1 d . . . O20 O 0.3343(3) 0.04283(6) -0.0088(3) 0.0935(10) Uani 1 1 d . . . C57 C 0.1505(3) 0.20544(7) 0.0199(3) 0.0527(9) Uani 1 1 d . . . C58 C 0.1135(3) 0.17518(7) 0.0236(3) 0.0551(9) Uani 1 1 d . . . H58A H 0.0365 0.1722 -0.0266 0.066 Uiso 1 1 calc R . . H58B H 0.0954 0.1720 0.0848 0.066 Uiso 1 1 calc R . . C59 C 0.2060(3) 0.15317(7) 0.0124(3) 0.0546(9) Uani 1 1 d . . . H59A H 0.2843 0.1558 0.0614 0.066 Uiso 1 1 calc R . . H59B H 0.2217 0.1551 -0.0502 0.066 Uiso 1 1 calc R . . C60 C 0.1718(4) 0.07176(7) 0.0191(3) 0.0623(10) Uani 1 1 d . . . H60A H 0.1541 0.0717 0.0813 0.075 Uiso 1 1 calc R . . H60B H 0.0922 0.0718 -0.0296 0.075 Uiso 1 1 calc R . . C61 C 0.2365(4) 0.04482(7) 0.0096(3) 0.0568(9) Uani 1 1 d . . . C62 C 0.2379(3) 0.09918(7) 0.0105(3) 0.0568(9) Uani 1 1 d . . . H62A H 0.2551 0.1002 -0.0517 0.068 Uiso 1 1 calc R . . H62B H 0.3167 0.1001 0.0601 0.068 Uiso 1 1 calc R . . C63 C 0.1547(3) 0.12392(7) 0.0218(3) 0.0573(9) Uani 1 1 d . . . H63A H 0.0750 0.1220 -0.0263 0.069 Uiso 1 1 calc R . . H63B H 0.1390 0.1225 0.0845 0.069 Uiso 1 1 calc R . . N7 N 0.2532(3) 0.02827(6) 0.4944(2) 0.0611(8) Uani 1 1 d . . . N8 N 0.1280(3) 0.22343(6) 0.5259(2) 0.0574(8) Uani 1 1 d . . . C64 C 0.1925(3) 0.16683(8) 0.5141(3) 0.0628(10) Uani 1 1 d . . . C65 C 0.1913(3) 0.08463(7) 0.5094(3) 0.0607(10) Uani 1 1 d . . . C66 C 0.2338(4) 0.13695(8) 0.5061(4) 0.0885(14) Uani 1 1 d . . . H66A H 0.2475 0.1347 0.4430 0.106 Uiso 1 1 calc R . . H66B H 0.3137 0.1343 0.5533 0.106 Uiso 1 1 calc R . . C67 C 0.1429(4) 0.03581(8) 0.5053(3) 0.0629(10) Uani 1 1 d . . . H67 H 0.0858 0.0217 0.5076 0.075 Uiso 1 1 calc R . . C68 C 0.1094(3) 0.06310(8) 0.5131(3) 0.0595(10) Uani 1 1 d . . . H68 H 0.0311 0.0673 0.5209 0.071 Uiso 1 1 calc R . . C69 C 0.3313(4) 0.04866(7) 0.4913(3) 0.0634(10) Uani 1 1 d . . . H69 H 0.4093 0.0438 0.4844 0.076 Uiso 1 1 calc R . . C70 C -0.3109(6) 0.38409(9) 0.5509(4) 0.1065(18) Uani 1 1 d . . . H70A H -0.2450 0.3783 0.6068 0.128 Uiso 1 1 calc R . . H70B H -0.3892 0.3827 0.5678 0.128 Uiso 1 1 calc R . . C71 C -0.3140(6) 0.36524(10) 0.4762(4) 0.129(2) Uani 1 1 d . . . H71A H -0.2361 0.3670 0.4589 0.154 Uiso 1 1 calc R . . H71B H -0.3804 0.3710 0.4207 0.154 Uiso 1 1 calc R . . C72 C 0.2720(3) 0.18847(8) 0.5076(3) 0.0632(10) Uani 1 1 d . . . H72 H 0.3499 0.1844 0.4990 0.076 Uiso 1 1 calc R . . C73 C 0.1520(4) 0.11470(8) 0.5191(4) 0.0837(13) Uani 1 1 d . . . H73A H 0.0716 0.1176 0.4728 0.100 Uiso 1 1 calc R . . H73B H 0.1397 0.1168 0.5827 0.100 Uiso 1 1 calc R . . C74 C 0.2370(3) 0.21597(7) 0.5136(3) 0.0585(10) Uani 1 1 d . . . H74 H 0.2928 0.2301 0.5088 0.070 Uiso 1 1 calc R . . C75 C 0.0512(3) 0.20284(7) 0.5330(3) 0.0616(10) Uani 1 1 d . . . H75 H -0.0259 0.2075 0.5421 0.074 Uiso 1 1 calc R . . C76 C 0.0802(3) 0.17455(8) 0.5273(3) 0.0654(10) Uani 1 1 d . . . H76 H 0.0229 0.1608 0.5325 0.078 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.064(2) 0.0385(16) 0.078(2) -0.0061(14) 0.0239(17) -0.0070(15) N2 0.066(2) 0.0427(17) 0.073(2) -0.0022(15) 0.0234(16) 0.0027(15) N3 0.069(2) 0.0397(17) 0.075(2) -0.0053(14) 0.0245(17) 0.0017(15) N4 0.072(2) 0.0446(18) 0.071(2) 0.0008(15) 0.0166(17) -0.0005(16) N5 0.064(2) 0.0403(16) 0.077(2) 0.0063(15) 0.0265(17) -0.0013(15) N6 0.081(2) 0.0378(16) 0.072(2) 0.0017(15) 0.0231(18) 0.0040(16) O1 0.0772(19) 0.0395(15) 0.119(2) -0.0016(15) 0.0465(17) -0.0049(13) O2 0.079(2) 0.0555(17) 0.151(3) 0.0003(17) 0.064(2) 0.0015(14) O3 0.0723(18) 0.0452(16) 0.127(2) 0.0046(15) 0.0517(17) 0.0027(14) O4 0.0794(19) 0.0444(16) 0.145(3) 0.0000(16) 0.0531(19) 0.0015(14) O5 0.072(2) 0.0549(17) 0.158(3) 0.0038(18) 0.049(2) -0.0088(15) O6 0.0724(18) 0.0369(15) 0.141(3) -0.0001(16) 0.0465(18) -0.0055(13) O7 0.0664(19) 0.0628(18) 0.170(3) -0.0024(19) 0.062(2) -0.0079(15) O8 0.076(2) 0.0514(17) 0.145(3) 0.0019(16) 0.056(2) -0.0005(14) O9 0.073(2) 0.0619(19) 0.167(3) 0.0097(19) 0.059(2) 0.0050(15) O10 0.0687(18) 0.0453(16) 0.147(3) -0.0025(17) 0.0437(18) -0.0050(14) O11 0.097(2) 0.0406(16) 0.140(3) 0.0080(16) 0.072(2) 0.0057(15) O16 0.0689(19) 0.0534(17) 0.162(3) 0.0061(18) 0.057(2) -0.0064(14) C1 0.062(2) 0.044(2) 0.079(3) 0.0010(18) 0.031(2) 0.0016(17) C2 0.060(2) 0.044(2) 0.075(3) 0.0039(18) 0.021(2) 0.0005(17) C3 0.062(2) 0.046(2) 0.066(2) 0.0033(17) 0.015(2) -0.0009(18) C4 0.056(2) 0.0412(19) 0.074(3) 0.0015(17) 0.0209(19) -0.0073(16) C5 0.064(2) 0.040(2) 0.066(2) -0.0023(17) 0.021(2) -0.0071(17) C6 0.059(2) 0.045(2) 0.068(2) 0.0029(17) 0.0229(19) -0.0031(17) C7 0.081(3) 0.050(2) 0.118(4) -0.001(2) 0.038(3) 0.003(2) C8 0.062(2) 0.045(2) 0.079(3) 0.0037(18) 0.024(2) -0.0057(17) C9 0.062(2) 0.044(2) 0.074(3) -0.0027(18) 0.017(2) 0.0024(17) C10 0.058(2) 0.040(2) 0.064(2) -0.0008(16) 0.0166(19) -0.0041(17) C11 0.068(3) 0.051(2) 0.103(3) -0.008(2) 0.035(2) 0.011(2) C12 0.074(3) 0.042(2) 0.087(3) 0.0005(19) 0.027(2) -0.0008(18) C13 0.081(3) 0.048(2) 0.138(4) -0.001(3) 0.040(3) 0.019(2) C14 0.062(2) 0.044(2) 0.073(3) 0.0055(18) 0.0184(19) 0.0030(17) C15 0.059(2) 0.0391(19) 0.077(3) 0.0039(17) 0.0233(19) 0.0023(16) C16 0.060(2) 0.056(2) 0.080(3) -0.005(2) 0.023(2) -0.0151(19) C17 0.081(3) 0.043(2) 0.109(3) 0.001(2) 0.045(3) 0.004(2) C18 0.068(3) 0.049(2) 0.088(3) 0.0011(19) 0.035(2) -0.0007(19) C19 0.065(2) 0.040(2) 0.070(2) 0.0043(17) 0.0228(19) -0.0033(17) C20 0.074(3) 0.040(2) 0.139(4) -0.003(2) 0.050(3) -0.0116(19) C21 0.054(2) 0.045(2) 0.069(2) 0.0044(17) 0.0254(19) 0.0011(17) C22 0.073(3) 0.053(2) 0.118(4) 0.002(2) 0.042(3) -0.013(2) C23 0.053(2) 0.048(2) 0.074(3) 0.0017(18) 0.0204(19) -0.0054(18) C24 0.064(3) 0.068(3) 0.090(3) -0.006(2) 0.026(2) 0.005(2) C25 0.062(2) 0.064(3) 0.099(3) -0.009(2) 0.037(2) 0.001(2) C26 0.068(3) 0.044(2) 0.097(3) 0.001(2) 0.027(2) -0.0011(19) C27 0.126(4) 0.056(3) 0.174(5) 0.002(3) 0.082(4) 0.021(3) C28 0.065(2) 0.045(2) 0.079(3) 0.0013(18) 0.023(2) -0.0023(18) C29 0.142(5) 0.052(3) 0.217(6) 0.006(3) 0.108(5) 0.011(3) C30 0.072(3) 0.045(2) 0.104(3) -0.001(2) 0.040(2) -0.0039(19) C31 0.054(2) 0.046(2) 0.097(3) -0.0052(19) 0.028(2) -0.0031(18) C32 0.061(2) 0.0395(19) 0.072(2) 0.0004(17) 0.0204(19) -0.0058(16) C33 0.071(3) 0.045(2) 0.078(3) -0.0002(18) 0.027(2) -0.0145(19) C34 0.054(2) 0.056(2) 0.083(3) 0.002(2) 0.024(2) 0.0085(19) C35 0.064(2) 0.047(2) 0.091(3) -0.001(2) 0.035(2) 0.0036(19) C36 0.065(2) 0.0402(19) 0.086(3) 0.0017(18) 0.038(2) -0.0013(17) C37 0.064(2) 0.0400(19) 0.066(2) 0.0005(16) 0.0236(19) -0.0034(16) C38 0.093(3) 0.048(2) 0.086(3) -0.002(2) 0.037(3) -0.012(2) C39 0.056(2) 0.050(2) 0.089(3) -0.002(2) 0.029(2) 0.0051(18) C40 0.070(3) 0.058(3) 0.074(3) -0.002(2) 0.022(2) 0.018(2) C41 0.054(2) 0.043(2) 0.073(3) 0.0039(17) 0.0211(19) -0.0011(17) C42 0.061(2) 0.039(2) 0.103(3) -0.0028(19) 0.032(2) -0.0071(17) C43 0.076(3) 0.054(2) 0.091(3) 0.004(2) 0.034(2) 0.019(2) C44 0.063(3) 0.064(3) 0.069(3) -0.001(2) 0.023(2) -0.015(2) C45 0.053(2) 0.056(2) 0.090(3) 0.000(2) 0.029(2) -0.0048(19) C46 0.058(2) 0.0397(19) 0.072(2) 0.0045(17) 0.0229(19) -0.0006(16) C47 0.122(5) 0.058(3) 0.271(9) 0.016(4) 0.088(5) 0.011(3) C48 0.074(3) 0.049(2) 0.090(3) 0.000(2) 0.033(2) 0.000(2) C49 0.056(2) 0.064(3) 0.081(3) -0.007(2) 0.030(2) -0.0114(19) C50 0.065(3) 0.048(2) 0.134(4) 0.000(2) 0.047(3) -0.0028(19) C51 0.167(7) 0.059(4) 0.328(11) 0.021(5) 0.123(7) 0.023(4) C52 0.092(3) 0.043(2) 0.090(3) -0.004(2) 0.041(3) -0.002(2) C53 0.060(3) 0.068(3) 0.101(3) -0.008(2) 0.037(2) -0.014(2) C54 0.080(3) 0.042(2) 0.117(4) 0.001(2) 0.038(3) 0.012(2) C55 0.062(3) 0.066(3) 0.124(4) -0.011(3) 0.044(3) 0.012(2) C56 0.069(3) 0.059(3) 0.088(3) -0.006(2) 0.033(2) -0.003(2) O17 0.0673(18) 0.0448(16) 0.114(2) 0.0050(15) 0.0441(16) 0.0009(14) O18 0.084(2) 0.0407(15) 0.131(3) -0.0030(16) 0.0493(18) -0.0104(14) O19 0.0663(19) 0.0530(17) 0.158(3) 0.0029(17) 0.0524(19) -0.0073(14) O20 0.084(2) 0.0581(18) 0.158(3) 0.0016(18) 0.067(2) 0.0031(15) C57 0.048(2) 0.044(2) 0.068(2) 0.0010(17) 0.0174(18) -0.0013(16) C58 0.048(2) 0.045(2) 0.073(2) 0.0031(17) 0.0182(18) -0.0040(16) C59 0.056(2) 0.046(2) 0.063(2) 0.0027(17) 0.0190(18) -0.0022(16) C60 0.070(2) 0.045(2) 0.077(3) 0.0028(18) 0.029(2) -0.0048(18) C61 0.063(2) 0.042(2) 0.067(2) -0.0015(17) 0.020(2) -0.0031(17) C62 0.062(2) 0.044(2) 0.066(2) 0.0016(17) 0.0180(18) -0.0019(17) C63 0.066(2) 0.047(2) 0.059(2) -0.0010(17) 0.0168(19) -0.0059(17) N7 0.072(2) 0.0369(16) 0.074(2) -0.0019(14) 0.0194(17) -0.0060(15) N8 0.0583(19) 0.0425(17) 0.073(2) -0.0048(14) 0.0210(16) 0.0019(14) C64 0.059(2) 0.048(2) 0.086(3) -0.0043(19) 0.028(2) 0.0081(18) C65 0.059(2) 0.044(2) 0.082(3) -0.0028(18) 0.024(2) -0.0013(18) C66 0.083(3) 0.051(2) 0.142(4) 0.000(3) 0.049(3) 0.010(2) C67 0.070(3) 0.051(2) 0.072(3) 0.0003(18) 0.027(2) -0.0178(19) C68 0.055(2) 0.055(2) 0.074(3) -0.0058(19) 0.0264(19) -0.0064(18) C69 0.061(2) 0.042(2) 0.091(3) -0.0054(19) 0.027(2) -0.0017(17) C70 0.159(5) 0.060(3) 0.118(4) -0.008(3) 0.068(4) -0.020(3) C71 0.230(7) 0.058(3) 0.118(4) -0.014(3) 0.082(5) -0.034(4) C72 0.052(2) 0.055(2) 0.088(3) -0.006(2) 0.028(2) 0.0009(18) C73 0.079(3) 0.047(2) 0.134(4) -0.004(2) 0.043(3) 0.003(2) C74 0.053(2) 0.048(2) 0.079(3) -0.0006(18) 0.025(2) -0.0045(17) C75 0.054(2) 0.051(2) 0.084(3) -0.0051(19) 0.027(2) 0.0059(18) C76 0.058(2) 0.048(2) 0.098(3) -0.003(2) 0.036(2) -0.0079(18) _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 C31 1.314(4) . ? N1 C33 1.342(4) . ? N2 C49 1.320(5) . ? N2 C39 1.324(4) . ? N3 C35 1.323(4) . ? N3 C16 1.339(5) . ? N4 C26 1.326(5) . ? N4 C44 1.336(5) . ? N5 C45 1.317(4) . ? N5 C34 1.323(5) . ? N6 C48 1.309(5) . ? N6 C40 1.326(5) . ? O1 C5 1.305(4) . ? O1 H1O 0.97(5) . ? O2 C5 1.212(4) . ? O3 C21 1.321(4) . ? O3 H3O 1.00(4) . ? O4 C23 1.314(4) . ? O4 H4O 1.21(3) . ? O5 C23 1.200(4) . ? O6 C10 1.311(4) . ? O6 H6O 1.05(5) . ? O7 C21 1.182(4) . ? O8 C10 1.195(4) . ? O9 C3 1.197(4) . ? O10 C3 1.312(4) . ? O10 H10O 1.07(4) . ? O11 C41 1.303(4) . ? O11 H11O 1.00(5) . ? O16 C41 1.208(4) . ? C1 C21 1.483(5) . ? C1 C6 1.509(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C4 1.510(5) . ? C2 C6 1.512(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C12 1.484(5) . ? C4 C15 1.511(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C15 1.480(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C24 1.373(6) . ? C7 C50 1.389(5) . ? C7 C47 1.493(6) . ? C8 C23 1.472(5) . ? C8 C14 1.524(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C12 1.503(5) . ? C9 C28 1.522(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C32 1.488(5) . ? C11 C30 1.368(5) . ? C11 C25 1.384(5) . ? C11 C27 1.496(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C55 1.355(6) . ? C13 C22 1.375(6) . ? C13 C51 1.512(6) . ? C14 C28 1.508(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C25 1.344(5) . ? C16 H16 0.9300 . ? C17 C18 1.368(5) . ? C17 C20 1.378(5) . ? C17 C29 1.506(6) . ? C18 C33 1.356(5) . ? C18 H18 0.9300 . ? C19 C46 1.518(4) . ? C19 C37 1.528(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C31 1.375(5) . ? C20 H20 0.9300 . ? C22 C39 1.375(5) . ? C22 H22 0.9300 . ? C24 C44 1.333(5) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? C26 C50 1.360(5) . ? C26 H26 0.9300 . ? C27 C29 1.393(5) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C35 1.360(5) . ? C30 H30 0.9300 . ? C31 H31 0.9300 . ? C32 C37 1.514(4) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 H33 0.9300 . ? C34 C53 1.358(5) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C36 C41 1.496(5) . ? C36 C46 1.505(4) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C43 1.358(5) . ? C38 C53 1.375(5) . ? C38 C71 1.513(6) . ? C39 H39 0.9300 . ? C40 C56 1.355(5) . ? C40 H40 0.9300 . ? C42 C65 1.371(5) . ? C42 C69 1.380(5) . ? C42 H42 0.9300 . ? C43 C45 1.374(5) . ? C43 H43 0.9300 . ? C44 H44 0.9300 . ? C45 H45 0.9300 . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C47 C51 1.338(6) . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C48 C54 1.366(5) . ? C48 H48 0.9300 . ? C49 C55 1.334(5) . ? C49 H49 0.9300 . ? C50 H50 0.9300 . ? C51 H51A 0.9700 . ? C51 H51B 0.9700 . ? C52 C54 1.372(6) . ? C52 C56 1.382(5) . ? C52 C70 1.508(5) . ? C53 H53 0.9300 . ? C54 H54 0.9300 . ? C55 H55 0.9300 . ? C56 H56 0.9300 . ? O17 C57 1.302(4) . ? O17 H17O 0.97(4) . ? O18 C61 1.315(4) . ? O18 H18O 1.07(5) . ? O19 C57 1.204(4) . ? O20 C61 1.193(4) . ? C57 C58 1.496(5) . ? C58 C59 1.505(5) . ? C58 H58A 0.9700 . ? C58 H58B 0.9700 . ? C59 C63 1.518(4) . ? C59 H59A 0.9700 . ? C59 H59B 0.9700 . ? C60 C61 1.490(5) . ? C60 C62 1.514(5) . ? C60 H60A 0.9700 . ? C60 H60B 0.9700 . ? C62 C63 1.530(5) . ? C62 H62A 0.9700 . ? C62 H62B 0.9700 . ? C63 H63A 0.9700 . ? C63 H63B 0.9700 . ? N7 C69 1.308(4) . ? N7 C67 1.329(5) . ? N8 C75 1.319(4) . ? N8 C74 1.322(4) . ? C64 C76 1.365(5) . ? C64 C72 1.374(5) . ? C64 C66 1.501(5) . ? C65 C68 1.378(5) . ? C65 C73 1.507(5) . ? C66 C73 1.437(6) . ? C66 H66A 0.9700 . ? C66 H66B 0.9700 . ? C67 C68 1.358(5) . ? C67 H67 0.9300 . ? C68 H68 0.9300 . ? C69 H69 0.9300 . ? C70 C71 1.392(6) . ? C70 H70A 0.9700 . ? C70 H70B 0.9700 . ? C71 H71A 0.9700 . ? C71 H71B 0.9700 . ? C72 C74 1.368(5) . ? C72 H72 0.9300 . ? C73 H73A 0.9700 . ? C73 H73B 0.9700 . ? C74 H74 0.9300 . ? C75 C76 1.385(5) . ? C75 H75 0.9300 . ? C76 H76 0.9300 . ? 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 C31 N1 C33 115.9(3) . . ? C49 N2 C39 118.0(3) . . ? C35 N3 C16 116.9(3) . . ? C26 N4 C44 116.7(3) . . ? C45 N5 C34 116.9(3) . . ? C48 N6 C40 117.3(3) . . ? C5 O1 H1O 115(3) . . ? C21 O3 H3O 109(2) . . ? C23 O4 H4O 112.4(15) . . ? C10 O6 H6O 111(2) . . ? C3 O10 H10O 111(2) . . ? C41 O11 H11O 118(3) . . ? C21 C1 C6 117.9(3) . . ? C21 C1 H1A 107.8 . . ? C6 C1 H1A 107.8 . . ? C21 C1 H1B 107.8 . . ? C6 C1 H1B 107.8 . . ? H1A C1 H1B 107.2 . . ? C4 C2 C6 116.6(3) . . ? C4 C2 H2A 108.2 . . ? C6 C2 H2A 108.2 . . ? C4 C2 H2B 108.2 . . ? C6 C2 H2B 108.2 . . ? H2A C2 H2B 107.3 . . ? O9 C3 O10 122.3(4) . . ? O9 C3 C12 125.7(4) . . ? O10 C3 C12 112.0(3) . . ? C2 C4 C15 110.4(3) . . ? C2 C4 H4A 109.6 . . ? C15 C4 H4A 109.6 . . ? C2 C4 H4B 109.6 . . ? C15 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? O2 C5 O1 122.0(3) . . ? O2 C5 C15 124.9(3) . . ? O1 C5 C15 113.1(3) . . ? C1 C6 C2 110.4(3) . . ? C1 C6 H6A 109.6 . . ? C2 C6 H6A 109.6 . . ? C1 C6 H6B 109.6 . . ? C2 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C24 C7 C50 116.1(4) . . ? C24 C7 C47 118.6(4) . . ? C50 C7 C47 125.2(4) . . ? C23 C8 C14 116.7(3) . . ? C23 C8 H8A 108.1 . . ? C14 C8 H8A 108.1 . . ? C23 C8 H8B 108.1 . . ? C14 C8 H8B 108.1 . . ? H8A C8 H8B 107.3 . . ? C12 C9 C28 108.4(3) . . ? C12 C9 H9A 110.0 . . ? C28 C9 H9A 110.0 . . ? C12 C9 H9B 110.0 . . ? C28 C9 H9B 110.0 . . ? H9A C9 H9B 108.4 . . ? O8 C10 O6 121.9(3) . . ? O8 C10 C32 125.8(3) . . ? O6 C10 C32 112.3(3) . . ? C30 C11 C25 115.1(4) . . ? C30 C11 C27 126.5(4) . . ? C25 C11 C27 118.3(4) . . ? C3 C12 C9 118.6(3) . . ? C3 C12 H12A 107.7 . . ? C9 C12 H12A 107.7 . . ? C3 C12 H12B 107.7 . . ? C9 C12 H12B 107.7 . . ? H12A C12 H12B 107.1 . . ? C55 C13 C22 116.5(4) . . ? C55 C13 C51 116.6(4) . . ? C22 C13 C51 126.8(5) . . ? C28 C14 C8 109.2(3) . . ? C28 C14 H14A 109.8 . . ? C8 C14 H14A 109.8 . . ? C28 C14 H14B 109.8 . . ? C8 C14 H14B 109.8 . . ? H14A C14 H14B 108.3 . . ? C5 C15 C4 117.1(3) . . ? C5 C15 H15A 108.0 . . ? C4 C15 H15A 108.0 . . ? C5 C15 H15B 108.0 . . ? C4 C15 H15B 108.0 . . ? H15A C15 H15B 107.3 . . ? N3 C16 C25 123.3(4) . . ? N3 C16 H16 118.3 . . ? C25 C16 H16 118.3 . . ? C18 C17 C20 117.4(4) . . ? C18 C17 C29 117.6(4) . . ? C20 C17 C29 124.9(4) . . ? C33 C18 C17 120.1(4) . . ? C33 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C46 C19 C37 115.9(3) . . ? C46 C19 H19A 108.3 . . ? C37 C19 H19A 108.3 . . ? C46 C19 H19B 108.3 . . ? C37 C19 H19B 108.3 . . ? H19A C19 H19B 107.4 . . ? C31 C20 C17 118.5(4) . . ? C31 C20 H20 120.8 . . ? C17 C20 H20 120.8 . . ? O7 C21 O3 122.3(3) . . ? O7 C21 C1 125.1(3) . . ? O3 C21 C1 112.5(3) . . ? C39 C22 C13 119.0(4) . . ? C39 C22 H22 120.5 . . ? C13 C22 H22 120.5 . . ? O5 C23 O4 121.6(3) . . ? O5 C23 C8 126.3(4) . . ? O4 C23 C8 112.2(3) . . ? C44 C24 C7 120.5(4) . . ? C44 C24 H24 119.8 . . ? C7 C24 H24 119.8 . . ? C16 C25 C11 120.6(4) . . ? C16 C25 H25 119.7 . . ? C11 C25 H25 119.7 . . ? N4 C26 C50 122.8(4) . . ? N4 C26 H26 118.6 . . ? C50 C26 H26 118.6 . . ? C29 C27 C11 117.9(4) . . ? C29 C27 H27A 107.8 . . ? C11 C27 H27A 107.8 . . ? C29 C27 H27B 107.8 . . ? C11 C27 H27B 107.8 . . ? H27A C27 H27B 107.2 . . ? C14 C28 C9 116.8(3) . . ? C14 C28 H28A 108.1 . . ? C9 C28 H28A 108.1 . . ? C14 C28 H28B 108.1 . . ? C9 C28 H28B 108.1 . . ? H28A C28 H28B 107.3 . . ? C27 C29 C17 120.2(4) . . ? C27 C29 H29A 107.3 . . ? C17 C29 H29A 107.3 . . ? C27 C29 H29B 107.3 . . ? C17 C29 H29B 107.3 . . ? H29A C29 H29B 106.9 . . ? C35 C30 C11 122.0(4) . . ? C35 C30 H30 119.0 . . ? C11 C30 H30 119.0 . . ? N1 C31 C20 124.7(4) . . ? N1 C31 H31 117.7 . . ? C20 C31 H31 117.7 . . ? C10 C32 C37 116.9(3) . . ? C10 C32 H32A 108.1 . . ? C37 C32 H32A 108.1 . . ? C10 C32 H32B 108.1 . . ? C37 C32 H32B 108.1 . . ? H32A C32 H32B 107.3 . . ? N1 C33 C18 123.4(3) . . ? N1 C33 H33 118.3 . . ? C18 C33 H33 118.3 . . ? N5 C34 C53 123.1(4) . . ? N5 C34 H34 118.4 . . ? C53 C34 H34 118.4 . . ? N3 C35 C30 122.0(4) . . ? N3 C35 H35 119.0 . . ? C30 C35 H35 119.0 . . ? C41 C36 C46 118.0(3) . . ? C41 C36 H36A 107.8 . . ? C46 C36 H36A 107.8 . . ? C41 C36 H36B 107.8 . . ? C46 C36 H36B 107.8 . . ? H36A C36 H36B 107.1 . . ? C32 C37 C19 108.7(3) . . ? C32 C37 H37A 109.9 . . ? C19 C37 H37A 109.9 . . ? C32 C37 H37B 109.9 . . ? C19 C37 H37B 109.9 . . ? H37A C37 H37B 108.3 . . ? C43 C38 C53 116.3(4) . . ? C43 C38 C71 122.3(5) . . ? C53 C38 C71 121.4(4) . . ? N2 C39 C22 122.5(4) . . ? N2 C39 H39 118.8 . . ? C22 C39 H39 118.8 . . ? N6 C40 C56 123.1(4) . . ? N6 C40 H40 118.5 . . ? C56 C40 H40 118.5 . . ? O16 C41 O11 123.0(3) . . ? O16 C41 C36 124.0(3) . . ? O11 C41 C36 112.9(3) . . ? C65 C42 C69 119.0(3) . . ? C65 C42 H42 120.5 . . ? C69 C42 H42 120.5 . . ? C38 C43 C45 120.3(4) . . ? C38 C43 H43 119.8 . . ? C45 C43 H43 119.8 . . ? C24 C44 N4 123.9(4) . . ? C24 C44 H44 118.0 . . ? N4 C44 H44 118.0 . . ? N5 C45 C43 123.0(4) . . ? N5 C45 H45 118.5 . . ? C43 C45 H45 118.5 . . ? C36 C46 C19 108.6(3) . . ? C36 C46 H46A 110.0 . . ? C19 C46 H46A 110.0 . . ? C36 C46 H46B 110.0 . . ? C19 C46 H46B 110.0 . . ? H46A C46 H46B 108.4 . . ? C51 C47 C7 119.4(5) . . ? C51 C47 H47A 107.5 . . ? C7 C47 H47A 107.5 . . ? C51 C47 H47B 107.5 . . ? C7 C47 H47B 107.5 . . ? H47A C47 H47B 107.0 . . ? N6 C48 C54 123.5(4) . . ? N6 C48 H48 118.2 . . ? C54 C48 H48 118.2 . . ? N2 C49 C55 121.8(4) . . ? N2 C49 H49 119.1 . . ? C55 C49 H49 119.1 . . ? C26 C50 C7 120.1(4) . . ? C26 C50 H50 120.0 . . ? C7 C50 H50 120.0 . . ? C47 C51 C13 120.7(5) . . ? C47 C51 H51A 107.1 . . ? C13 C51 H51A 107.1 . . ? C47 C51 H51B 107.1 . . ? C13 C51 H51B 107.1 . . ? H51A C51 H51B 106.8 . . ? C54 C52 C56 116.5(4) . . ? C54 C52 C70 122.1(4) . . ? C56 C52 C70 121.3(4) . . ? C34 C53 C38 120.3(4) . . ? C34 C53 H53 119.8 . . ? C38 C53 H53 119.8 . . ? C48 C54 C52 119.6(4) . . ? C48 C54 H54 120.2 . . ? C52 C54 H54 120.2 . . ? C49 C55 C13 122.2(4) . . ? C49 C55 H55 118.9 . . ? C13 C55 H55 118.9 . . ? C40 C56 C52 119.9(4) . . ? C40 C56 H56 120.0 . . ? C52 C56 H56 120.0 . . ? C57 O17 H17O 115(3) . . ? C61 O18 H18O 112(3) . . ? O19 C57 O17 123.2(3) . . ? O19 C57 C58 123.7(3) . . ? O17 C57 C58 113.1(3) . . ? C57 C58 C59 117.1(3) . . ? C57 C58 H58A 108.0 . . ? C59 C58 H58A 108.0 . . ? C57 C58 H58B 108.0 . . ? C59 C58 H58B 108.0 . . ? H58A C58 H58B 107.3 . . ? C58 C59 C63 109.6(3) . . ? C58 C59 H59A 109.7 . . ? C63 C59 H59A 109.7 . . ? C58 C59 H59B 109.7 . . ? C63 C59 H59B 109.7 . . ? H59A C59 H59B 108.2 . . ? C61 C60 C62 117.9(3) . . ? C61 C60 H60A 107.8 . . ? C62 C60 H60A 107.8 . . ? C61 C60 H60B 107.8 . . ? C62 C60 H60B 107.8 . . ? H60A C60 H60B 107.2 . . ? O20 C61 O18 122.9(3) . . ? O20 C61 C60 125.6(3) . . ? O18 C61 C60 111.5(3) . . ? C60 C62 C63 109.0(3) . . ? C60 C62 H62A 109.9 . . ? C63 C62 H62A 109.9 . . ? C60 C62 H62B 109.9 . . ? C63 C62 H62B 109.9 . . ? H62A C62 H62B 108.3 . . ? C59 C63 C62 115.7(3) . . ? C59 C63 H63A 108.3 . . ? C62 C63 H63A 108.3 . . ? C59 C63 H63B 108.3 . . ? C62 C63 H63B 108.3 . . ? H63A C63 H63B 107.4 . . ? C69 N7 C67 116.8(3) . . ? C75 N8 C74 116.8(3) . . ? C76 C64 C72 116.2(3) . . ? C76 C64 C66 125.1(4) . . ? C72 C64 C66 118.7(3) . . ? C42 C65 C68 116.9(3) . . ? C42 C65 C73 124.2(3) . . ? C68 C65 C73 118.9(3) . . ? C73 C66 C64 117.5(4) . . ? C73 C66 H66A 107.9 . . ? C64 C66 H66A 107.9 . . ? C73 C66 H66B 107.9 . . ? C64 C66 H66B 107.9 . . ? H66A C66 H66B 107.2 . . ? N7 C67 C68 123.3(3) . . ? N7 C67 H67 118.3 . . ? C68 C67 H67 118.3 . . ? C67 C68 C65 120.0(3) . . ? C67 C68 H68 120.0 . . ? C65 C68 H68 120.0 . . ? N7 C69 C42 124.0(4) . . ? N7 C69 H69 118.0 . . ? C42 C69 H69 118.0 . . ? C71 C70 C52 115.2(4) . . ? C71 C70 H70A 108.5 . . ? C52 C70 H70A 108.5 . . ? C71 C70 H70B 108.5 . . ? C52 C70 H70B 108.5 . . ? H70A C70 H70B 107.5 . . ? C70 C71 C38 116.6(4) . . ? C70 C71 H71A 108.1 . . ? C38 C71 H71A 108.1 . . ? C70 C71 H71B 108.1 . . ? C38 C71 H71B 108.1 . . ? H71A C71 H71B 107.3 . . ? C74 C72 C64 120.3(3) . . ? C74 C72 H72 119.8 . . ? C64 C72 H72 119.8 . . ? C66 C73 C65 118.0(4) . . ? C66 C73 H73A 107.8 . . ? C65 C73 H73A 107.8 . . ? C66 C73 H73B 107.8 . . ? C65 C73 H73B 107.8 . . ? H73A C73 H73B 107.1 . . ? N8 C74 C72 123.4(3) . . ? N8 C74 H74 118.3 . . ? C72 C74 H74 118.3 . . ? N8 C75 C76 122.9(3) . . ? N8 C75 H75 118.5 . . ? C76 C75 H75 118.5 . . ? C64 C76 C75 120.3(3) . . ? C64 C76 H76 119.9 . . ? C75 C76 H76 119.9 . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.525 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.054