# Electronic Supplementary Material (ESI) for Catalysis Science & Technology # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_heme6_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H14 N4 O5' _chemical_formula_weight 306.2774 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.964(4) _cell_length_b 9.189(4) _cell_length_c 11.432(5) _cell_angle_alpha 69.34(2) _cell_angle_beta 89.43(2) _cell_angle_gamma 80.99(2) _cell_volume 869.2(7) _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 ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.170 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type ? _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 7532 _diffrn_reflns_av_R_equivalents 0.0827 _diffrn_reflns_av_sigmaI/netI 0.1175 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 27.89 _reflns_number_total 3903 _reflns_number_gt 2042 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.2000P)^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 3903 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1578 _refine_ls_R_factor_gt 0.0986 _refine_ls_wR_factor_ref 0.3321 _refine_ls_wR_factor_gt 0.2769 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5733(3) 0.4313(3) 0.13679(19) 0.0569(7) Uani 1 1 d . . . O4 O 0.7063(4) 0.5454(4) 0.4032(3) 0.0882(10) Uani 1 1 d . . . N3 N 0.8567(4) 0.6396(3) 0.0316(2) 0.0523(8) Uani 1 1 d . . . C1 C 0.8199(4) 0.3404(4) 0.3366(3) 0.0473(8) Uani 1 1 d . . . O3 O 0.9199(4) 0.0061(4) 0.3181(3) 0.0807(10) Uani 1 1 d . . . N4 N 0.4428(4) 0.2517(4) 0.2485(3) 0.0608(9) Uani 1 1 d . . . C5 C 0.8210(4) 0.4592(3) 0.2072(3) 0.0454(8) Uani 1 1 d . . . C2 C 0.6801(4) 0.2645(3) 0.3412(2) 0.0456(8) Uani 1 1 d . . . C7 C 1.0749(5) 0.5721(4) 0.1831(3) 0.0599(10) Uani 1 1 d . . . H7A H 1.1129 0.6516 0.1154 0.090 Uiso 1 1 calc R . . H7B H 1.1419 0.4735 0.2022 0.090 Uiso 1 1 calc R . . H7C H 1.0688 0.6022 0.2555 0.090 Uiso 1 1 calc R . . N2 N 0.7197(4) 0.6067(3) 0.0113(2) 0.0560(8) Uani 1 1 d . . . C12 C 0.9655(5) 0.2164(4) 0.3714(3) 0.0611(10) Uani 1 1 d . . . H12A H 1.0517 0.2688 0.3705 0.073 Uiso 1 1 calc R . . H12B H 0.9599 0.1424 0.4557 0.073 Uiso 1 1 calc R . . C8 C 0.6655(4) 0.1357(4) 0.4505(3) 0.0542(9) Uani 1 1 d . . . C6 C 0.9224(4) 0.5550(4) 0.1461(3) 0.0479(8) Uani 1 1 d . . . N6 N 0.6564(4) 0.0318(4) 0.5416(3) 0.0774(12) Uani 1 1 d . . . C3 C 0.5686(4) 0.3106(4) 0.2475(3) 0.0478(8) Uani 1 1 d . . . C10 C 0.8073(5) 0.4189(4) 0.4343(3) 0.0579(10) Uani 1 1 d . . . O5 O 0.8763(8) 0.3717(6) 0.5308(4) 0.153(2) Uani 1 1 d . . . C4 C 0.7009(4) 0.4967(4) 0.1189(3) 0.0478(8) Uani 1 1 d . . . O2 O 1.0622(7) 0.1664(4) 0.1949(4) 0.143(2) Uani 1 1 d . . . C13 C 0.9885(5) 0.1296(4) 0.2848(3) 0.0703(12) Uani 1 1 d . . . C11 C 0.6771(8) 0.6268(8) 0.4887(5) 0.1031(18) Uani 1 1 d . . . H11A H 0.5999 0.7172 0.4526 0.155 Uiso 1 1 calc R . . H11B H 0.7679 0.6605 0.5057 0.155 Uiso 1 1 calc R . . H11C H 0.6437 0.5577 0.5652 0.155 Uiso 1 1 calc R . . C14 C 0.9304(12) -0.0807(8) 0.2353(6) 0.137(3) Uani 1 1 d . . . H14A H 0.8773 -0.1685 0.2682 0.206 Uiso 1 1 calc R . . H14B H 1.0348 -0.1186 0.2277 0.206 Uiso 1 1 calc R . . H14C H 0.8862 -0.0133 0.1545 0.206 Uiso 1 1 calc R . . C96 C 0.4135(17) -0.1877(17) 0.1863(15) 0.202(6) Uani 1 1 d . . . C92 C 0.317(4) -0.115(3) 0.033(3) 0.324(15) Uani 1 1 d . . . C94 C 0.5000 0.0000 0.0000 0.098(2) Uani 1 2 d S . . C95 C 0.489(4) -0.084(2) 0.093(2) 0.327(17) Uani 1 1 d . . . H909 H 0.895(4) 0.712(4) -0.025(3) 0.043(8) Uiso 1 1 d . . . H4A H 0.424(4) 0.178(4) 0.307(3) 0.038(8) Uiso 1 1 d . . . H4B H 0.390(5) 0.284(6) 0.170(5) 0.079(13) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0665(16) 0.0495(13) 0.0347(11) 0.0132(10) -0.0126(9) -0.0171(12) O4 0.099(2) 0.096(2) 0.0701(18) -0.0485(17) -0.0241(16) 0.0301(19) N3 0.071(2) 0.0408(14) 0.0367(13) 0.0002(11) 0.0018(12) -0.0165(14) C1 0.059(2) 0.0363(15) 0.0345(14) 0.0005(12) -0.0040(12) -0.0027(14) O3 0.107(3) 0.0605(17) 0.0653(17) -0.0167(14) 0.0149(16) -0.0003(17) N4 0.070(2) 0.0563(17) 0.0387(14) 0.0079(13) -0.0086(13) -0.0191(16) C5 0.060(2) 0.0331(14) 0.0332(14) -0.0018(11) -0.0017(12) -0.0020(13) C2 0.059(2) 0.0359(15) 0.0303(13) 0.0014(11) -0.0037(12) -0.0040(14) C7 0.070(2) 0.0487(19) 0.058(2) -0.0151(16) 0.0015(16) -0.0112(17) N2 0.074(2) 0.0495(15) 0.0350(13) 0.0014(11) -0.0046(12) -0.0197(15) C12 0.064(2) 0.0456(18) 0.0493(18) 0.0085(15) -0.0088(15) 0.0021(16) C8 0.063(2) 0.0490(18) 0.0380(16) 0.0017(14) -0.0048(13) -0.0115(16) C6 0.065(2) 0.0363(15) 0.0355(14) -0.0071(12) 0.0002(13) -0.0025(14) N6 0.082(2) 0.074(2) 0.0478(16) 0.0182(16) -0.0080(14) -0.0231(19) C3 0.062(2) 0.0359(15) 0.0319(14) 0.0043(12) -0.0022(12) -0.0062(14) C10 0.078(3) 0.0491(18) 0.0394(16) -0.0072(14) -0.0064(15) -0.0088(18) O5 0.232(6) 0.123(3) 0.088(3) -0.057(3) -0.094(3) 0.065(3) C4 0.064(2) 0.0355(15) 0.0322(13) 0.0022(11) -0.0036(12) -0.0060(14) O2 0.216(5) 0.068(2) 0.099(3) 0.0108(19) 0.094(3) 0.007(3) C13 0.091(3) 0.0447(19) 0.0444(18) 0.0099(15) 0.0101(17) 0.0169(19) C11 0.119(5) 0.114(4) 0.093(4) -0.068(3) -0.005(3) 0.007(4) C14 0.232(9) 0.081(4) 0.093(4) -0.043(3) -0.005(5) 0.023(5) C96 0.198(12) 0.177(11) 0.224(14) -0.052(10) 0.055(10) -0.055(11) C92 0.44(4) 0.23(2) 0.30(3) -0.062(18) 0.16(3) -0.15(3) C94 0.094(5) 0.080(5) 0.111(6) -0.023(5) -0.005(5) -0.012(4) C95 0.55(5) 0.133(12) 0.29(2) -0.080(14) 0.18(3) -0.019(19) _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 1.355(4) . ? O1 C3 1.362(3) . ? O4 C10 1.297(5) . ? O4 C11 1.425(6) . ? N3 C6 1.348(4) . ? N3 N2 1.351(4) . ? C1 C5 1.499(4) . ? C1 C2 1.518(5) . ? C1 C10 1.523(5) . ? C1 C12 1.545(5) . ? O3 C13 1.312(5) . ? O3 C14 1.431(7) . ? N4 C3 1.323(5) . ? C5 C6 1.376(4) . ? C5 C4 1.398(5) . ? C2 C3 1.376(5) . ? C2 C8 1.408(4) . ? C7 C6 1.483(6) . ? N2 C4 1.317(4) . ? C12 C13 1.470(6) . ? C8 N6 1.150(4) . ? C10 O5 1.175(5) . ? O2 C13 1.191(5) . ? C96 C95 1.41(2) . ? C96 C92 1.81(4) . ? C92 C95 1.79(5) . ? C94 C95 1.08(2) . ? C94 C95 1.08(2) 2_655 ? 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 C3 116.1(2) . . ? C10 O4 C11 119.3(4) . . ? C6 N3 N2 114.8(3) . . ? C5 C1 C2 106.9(2) . . ? C5 C1 C10 111.3(3) . . ? C2 C1 C10 107.8(3) . . ? C5 C1 C12 112.1(3) . . ? C2 C1 C12 111.6(3) . . ? C10 C1 C12 107.1(3) . . ? C13 O3 C14 116.1(4) . . ? C6 C5 C4 104.1(3) . . ? C6 C5 C1 133.5(3) . . ? C4 C5 C1 122.4(3) . . ? C3 C2 C8 118.0(3) . . ? C3 C2 C1 125.4(2) . . ? C8 C2 C1 116.5(3) . . ? C4 N2 N3 101.9(3) . . ? C13 C12 C1 112.2(3) . . ? N6 C8 C2 178.1(4) . . ? N3 C6 C5 105.2(3) . . ? N3 C6 C7 122.0(3) . . ? C5 C6 C7 132.7(3) . . ? N4 C3 O1 109.5(3) . . ? N4 C3 C2 127.7(3) . . ? O1 C3 C2 122.8(3) . . ? O5 C10 O4 121.1(4) . . ? O5 C10 C1 125.6(4) . . ? O4 C10 C1 113.2(3) . . ? N2 C4 O1 120.3(3) . . ? N2 C4 C5 114.0(3) . . ? O1 C4 C5 125.7(2) . . ? O2 C13 O3 123.6(5) . . ? O2 C13 C12 123.8(5) . . ? O3 C13 C12 112.5(3) . . ? C95 C96 C92 66.4(17) . . ? C95 C92 C96 46.0(13) . . ? C95 C94 C95 180(4) . 2_655 ? C94 C95 C96 154(4) . . ? C94 C95 C92 87(3) . . ? C96 C95 C92 67.6(17) . . ? _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 27.89 _diffrn_measured_fraction_theta_full 1.126 _refine_diff_density_max 0.427 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.094 _database_code_depnum_ccdc_archive 'CCDC 959948' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_matrix_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H15 N2 O7' _chemical_formula_weight 395.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8507(19) _cell_length_b 8.480(2) _cell_length_c 15.770(4) _cell_angle_alpha 96.715(8) _cell_angle_beta 90.412(9) _cell_angle_gamma 109.096(8) _cell_volume 984.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 410 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9959 _exptl_absorpt_correction_T_max 0.9979 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 13384 _diffrn_reflns_av_R_equivalents 0.1340 _diffrn_reflns_av_sigmaI/netI 0.0923 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.30 _diffrn_reflns_theta_max 30.77 _reflns_number_total 5229 _reflns_number_gt 3213 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.1157P)^2^+0.2969P] 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 5229 _refine_ls_number_parameters 269 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1119 _refine_ls_R_factor_gt 0.0758 _refine_ls_wR_factor_ref 0.2487 _refine_ls_wR_factor_gt 0.2079 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.7559(2) 0.30140(18) 0.02150(9) 0.0481(4) Uani 1 1 d . . . O2 O 0.7355(3) 0.1042(2) 0.10436(11) 0.0653(6) Uani 1 1 d . . . O3 O 0.6346(2) 0.60582(16) 0.21824(8) 0.0399(4) Uani 1 1 d . . . N1 N 0.5457(3) 0.6704(2) 0.34668(11) 0.0508(6) Uani 1 1 d . . . H4A H 0.5430 0.6507 0.3919 0.076 Uiso 1 1 calc R . . O4 O 1.0510(4) 0.5472(4) 0.26142(13) 0.0997(9) Uani 1 1 d . . . O6 O 0.3852(3) 0.0864(2) 0.20300(13) 0.0617(5) Uani 1 1 d . . . O7 O 0.5573(4) -0.0015(2) 0.28664(14) 0.0804(7) Uani 1 1 d . . . O5 O 0.9987(3) 0.5133(3) 0.39602(12) 0.0819(7) Uani 1 1 d . . . N2 N 0.4737(4) 0.3067(3) 0.45817(14) 0.0715(7) Uani 1 1 d . . . C1 C 0.7784(4) 0.6608(3) -0.08589(14) 0.0534(6) Uani 1 1 d . . . H1 H 0.8017 0.6947 -0.1398 0.064 Uiso 1 1 calc R . . C2 C 0.7866(4) 0.5073(3) -0.07106(14) 0.0490(6) Uani 1 1 d . . . H2 H 0.8170 0.4380 -0.1142 0.059 Uiso 1 1 calc R . . C3 C 0.7490(3) 0.4566(2) 0.00931(12) 0.0390(5) Uani 1 1 d . . . C4 C 0.7256(3) 0.2415(3) 0.09960(13) 0.0441(5) Uani 1 1 d . . . C5 C 0.6847(3) 0.3484(2) 0.16969(12) 0.0356(4) Uani 1 1 d . . . C6 C 0.6642(3) 0.2871(2) 0.25663(12) 0.0395(5) Uani 1 1 d . . . C7 C 0.8470(4) 0.2876(3) 0.29534(16) 0.0559(6) Uani 1 1 d . . . H7A H 0.8262 0.2360 0.3477 0.067 Uiso 1 1 calc R . . H7B H 0.8979 0.2210 0.2556 0.067 Uiso 1 1 calc R . . C8 C 0.9785(4) 0.4618(4) 0.31404(15) 0.0553(6) Uani 1 1 d . . . C9 C 1.1206(5) 0.6822(5) 0.4254(2) 0.0899(11) Uani 1 1 d . . . H9A H 1.2008 0.6780 0.4715 0.108 Uiso 1 1 calc R . . H9B H 1.1935 0.7278 0.3789 0.108 Uiso 1 1 calc R . . C10 C 1.0167(8) 0.7894(7) 0.4551(4) 0.1288(18) Uani 1 1 d . . . H10A H 0.9564 0.8120 0.4071 0.193 Uiso 1 1 calc R . . H10B H 1.0960 0.8934 0.4845 0.193 Uiso 1 1 calc R . . H10C H 0.9288 0.7339 0.4934 0.193 Uiso 1 1 calc R . . C11 C 0.6732(3) 0.4981(2) 0.15624(11) 0.0332(4) Uani 1 1 d . . . C12 C 0.5867(3) 0.5524(3) 0.29609(12) 0.0365(5) Uani 1 1 d . . . C13 C 0.5860(3) 0.3996(2) 0.31419(12) 0.0375(5) Uani 1 1 d . . . C14 C 0.5246(4) 0.3500(3) 0.39436(13) 0.0462(6) Uani 1 1 d . . . C15 C 0.5317(4) 0.1044(3) 0.24972(14) 0.0516(6) Uani 1 1 d . . . C16 C 0.2415(6) -0.0761(4) 0.1940(3) 0.0921(12) Uani 1 1 d . . . H16A H 0.2357 -0.1316 0.1362 0.111 Uiso 1 1 calc R . . H16B H 0.2676 -0.1468 0.2329 0.111 Uiso 1 1 calc R . . C17 C 0.0794(7) -0.0563(7) 0.2114(6) 0.194(4) Uani 1 1 d . . . H17A H 0.0845 -0.0031 0.2690 0.291 Uiso 1 1 calc R . . H17B H -0.0134 -0.1644 0.2051 0.291 Uiso 1 1 calc R . . H17C H 0.0529 0.0125 0.1725 0.291 Uiso 1 1 calc R . . C18 C 0.7059(3) 0.5601(2) 0.07468(11) 0.0344(4) Uani 1 1 d . . . C19 C 0.6993(3) 0.7167(3) 0.05862(13) 0.0430(5) Uani 1 1 d . . . H19 H 0.6704 0.7870 0.1017 0.052 Uiso 1 1 calc R . . C20 C 0.7357(4) 0.7666(3) -0.02151(15) 0.0526(6) Uani 1 1 d . . . H20 H 0.7317 0.8708 -0.0324 0.063 Uiso 1 1 calc R . . H4B H 0.538(3) 0.758(3) 0.3267(15) 0.039(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0815(12) 0.0303(8) 0.0358(7) 0.0042(6) 0.0176(7) 0.0225(8) O2 0.1193(17) 0.0346(9) 0.0531(10) 0.0079(7) 0.0230(10) 0.0392(10) O3 0.0699(10) 0.0246(7) 0.0297(6) 0.0079(5) 0.0152(6) 0.0201(7) N1 0.0931(17) 0.0389(10) 0.0342(8) 0.0127(7) 0.0187(9) 0.0373(11) O4 0.1047(19) 0.111(2) 0.0486(11) 0.0195(12) 0.0155(11) -0.0156(15) O6 0.0727(13) 0.0257(8) 0.0787(12) 0.0131(8) 0.0072(10) 0.0031(8) O7 0.139(2) 0.0334(9) 0.0729(12) 0.0251(9) 0.0047(12) 0.0276(11) O5 0.0943(16) 0.0916(16) 0.0426(10) 0.0071(10) 0.0127(10) 0.0076(13) N2 0.119(2) 0.0600(14) 0.0458(11) 0.0225(10) 0.0307(12) 0.0368(14) C1 0.0766(18) 0.0481(13) 0.0345(10) 0.0164(9) 0.0157(11) 0.0150(12) C2 0.0700(16) 0.0415(12) 0.0329(9) 0.0043(8) 0.0173(10) 0.0147(11) C3 0.0533(13) 0.0269(9) 0.0343(9) 0.0054(7) 0.0094(8) 0.0092(9) C4 0.0675(15) 0.0280(10) 0.0380(10) 0.0055(8) 0.0127(10) 0.0165(10) C5 0.0521(13) 0.0248(9) 0.0298(8) 0.0062(7) 0.0093(8) 0.0116(8) C6 0.0637(14) 0.0245(9) 0.0338(9) 0.0096(7) 0.0104(9) 0.0170(9) C7 0.0792(18) 0.0561(15) 0.0472(12) 0.0151(11) 0.0085(12) 0.0391(14) C8 0.0591(16) 0.0702(17) 0.0412(11) 0.0119(11) 0.0089(11) 0.0257(13) C9 0.081(2) 0.098(3) 0.0684(19) -0.0079(18) 0.0011(17) 0.005(2) C10 0.116(4) 0.101(4) 0.158(5) -0.014(3) 0.005(3) 0.030(3) C11 0.0481(12) 0.0220(8) 0.0283(8) 0.0037(7) 0.0079(8) 0.0096(8) C12 0.0511(12) 0.0313(9) 0.0295(8) 0.0082(7) 0.0103(8) 0.0154(9) C13 0.0560(13) 0.0277(9) 0.0308(8) 0.0086(7) 0.0112(8) 0.0148(9) C14 0.0726(16) 0.0316(10) 0.0376(10) 0.0096(8) 0.0129(10) 0.0195(10) C15 0.090(2) 0.0266(10) 0.0413(10) 0.0103(8) 0.0176(12) 0.0209(11) C16 0.111(3) 0.0365(15) 0.104(3) 0.0068(15) 0.021(2) -0.0094(17) C17 0.073(3) 0.096(4) 0.402(12) 0.117(6) -0.028(5) -0.016(3) C18 0.0485(12) 0.0227(9) 0.0296(8) 0.0064(7) 0.0074(8) 0.0072(8) C19 0.0652(15) 0.0293(10) 0.0355(9) 0.0078(8) 0.0098(9) 0.0153(10) C20 0.0839(18) 0.0345(11) 0.0430(11) 0.0182(9) 0.0154(11) 0.0195(11) _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 1.370(2) . ? O1 C4 1.380(2) . ? O2 C4 1.202(3) . ? O3 C11 1.363(2) . ? O3 C12 1.371(2) . ? N1 C12 1.330(3) . ? N1 H4A 0.7500 . ? N1 H4B 0.86(3) . ? O4 C8 1.189(3) . ? O6 C15 1.317(3) . ? O6 C16 1.459(4) . ? O7 C15 1.193(3) . ? O5 C8 1.307(3) . ? O5 C9 1.457(4) . ? N2 C14 1.142(3) . ? C1 C2 1.371(3) . ? C1 C20 1.392(3) . ? C1 H1 0.9300 . ? C2 C3 1.388(3) . ? C2 H2 0.9300 . ? C3 C18 1.391(3) . ? C4 C5 1.452(3) . ? C5 C11 1.343(3) . ? C5 C6 1.514(2) . ? C6 C13 1.516(3) . ? C6 C15 1.549(3) . ? C6 C7 1.554(4) . ? C7 C8 1.493(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C9 C10 1.451(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C18 1.439(2) . ? C12 C13 1.358(3) . ? C13 C14 1.417(3) . ? C16 C17 1.363(8) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.398(3) . ? C19 C20 1.382(3) . ? C19 H19 0.9300 . ? C20 H20 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 C3 O1 C4 121.94(15) . . ? C11 O3 C12 118.60(14) . . ? C12 N1 H4A 109.5 . . ? C12 N1 H4B 120.2(16) . . ? H4A N1 H4B 129.9 . . ? C15 O6 C16 118.2(3) . . ? C8 O5 C9 118.7(2) . . ? C2 C1 C20 121.05(19) . . ? C2 C1 H1 119.5 . . ? C20 C1 H1 119.5 . . ? C1 C2 C3 119.1(2) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? O1 C3 C2 117.49(18) . . ? O1 C3 C18 121.55(16) . . ? C2 C3 C18 120.96(19) . . ? O2 C4 O1 117.23(18) . . ? O2 C4 C5 124.98(19) . . ? O1 C4 C5 117.79(17) . . ? C11 C5 C4 119.66(16) . . ? C11 C5 C6 122.79(16) . . ? C4 C5 C6 117.51(16) . . ? C5 C6 C13 107.83(15) . . ? C5 C6 C15 110.39(17) . . ? C13 C6 C15 108.39(18) . . ? C5 C6 C7 111.74(18) . . ? C13 C6 C7 111.01(18) . . ? C15 C6 C7 107.44(18) . . ? C8 C7 C6 111.75(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 . . ? O4 C8 O5 123.4(3) . . ? O4 C8 C7 124.9(2) . . ? O5 C8 C7 111.6(2) . . ? C10 C9 O5 109.6(4) . . ? C10 C9 H9A 109.8 . . ? O5 C9 H9A 109.8 . . ? C10 C9 H9B 109.8 . . ? O5 C9 H9B 109.8 . . ? H9A C9 H9B 108.2 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C5 C11 O3 123.49(16) . . ? C5 C11 C18 122.19(16) . . ? O3 C11 C18 114.31(15) . . ? N1 C12 C13 128.08(17) . . ? N1 C12 O3 110.11(16) . . ? C13 C12 O3 121.81(17) . . ? C12 C13 C14 118.24(17) . . ? C12 C13 C6 123.13(16) . . ? C14 C13 C6 118.36(17) . . ? N2 C14 C13 178.6(3) . . ? O7 C15 O6 125.5(3) . . ? O7 C15 C6 123.2(3) . . ? O6 C15 C6 111.15(18) . . ? C17 C16 O6 110.7(4) . . ? C17 C16 H16A 109.5 . . ? O6 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? O6 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C3 C18 C19 119.23(16) . . ? C3 C18 C11 116.83(17) . . ? C19 C18 C11 123.93(17) . . ? C20 C19 C18 119.78(19) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C1 119.9(2) . . ? C19 C20 H20 120.0 . . ? C1 C20 H20 120.0 . . ? _diffrn_measured_fraction_theta_max 0.850 _diffrn_reflns_theta_full 30.77 _diffrn_measured_fraction_theta_full 1.126 _refine_diff_density_max 0.536 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.075 _database_code_depnum_ccdc_archive 'CCDC 959885' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ardkp71013_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H22 N4 O7' _chemical_formula_weight 454.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.549(5) _cell_length_b 11.180(5) _cell_length_c 12.730(5) _cell_angle_alpha 91.165(5) _cell_angle_beta 104.363(5) _cell_angle_gamma 110.189(5) _cell_volume 1098.7(9) _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 ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9795 _exptl_absorpt_correction_T_max 0.9876 _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 7941 _diffrn_reflns_av_R_equivalents 0.1422 _diffrn_reflns_av_sigmaI/netI 0.1089 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.73 _reflns_number_total 4028 _reflns_number_gt 2633 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.1047P)^2^+0.1902P] 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 4028 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1002 _refine_ls_R_factor_gt 0.0699 _refine_ls_wR_factor_ref 0.2153 _refine_ls_wR_factor_gt 0.1858 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 O3 O 0.4469(2) -0.03223(17) 0.84247(15) 0.0517(5) Uani 1 1 d . . . C8 C 0.9098(4) 0.1340(3) 0.8783(2) 0.0570(7) Uani 1 1 d . . . N2 N 0.1892(3) 0.1119(2) 0.67495(18) 0.0519(6) Uani 1 1 d . . . O10 O 0.6731(3) 0.12983(19) 0.60773(15) 0.0635(6) Uani 1 1 d . . . N1 N 0.2143(3) 0.0190(2) 0.73681(17) 0.0458(5) Uani 1 1 d . . . O2 O 0.2206(3) 0.3217(2) 0.57486(19) 0.0748(7) Uani 1 1 d . . . O1 O 0.5089(3) 0.3872(2) 0.6278(2) 0.0851(8) Uani 1 1 d . . . O5 O 0.5860(3) 0.2531(2) 0.98127(18) 0.0802(7) Uani 1 1 d . . . O11 O 0.8697(3) 0.3232(2) 0.67725(19) 0.0775(7) Uani 1 1 d . . . C13 C 0.4790(3) 0.1577(2) 0.7465(2) 0.0449(6) Uani 1 1 d . . . N3 N 0.6710(4) -0.0846(3) 0.9269(2) 0.0675(8) Uani 1 1 d . . . C26 C 0.7467(4) 0.3423(3) 0.8538(2) 0.0524(7) Uani 1 1 d . . . H26A H 0.8721 0.3721 0.8723 0.063 Uiso 1 1 calc R . . H26B H 0.7109 0.4042 0.8116 0.063 Uiso 1 1 calc R . . C1 C 0.0690(4) -0.0874(2) 0.7456(2) 0.0488(7) Uani 1 1 d . . . C10 C 0.6243(4) 0.0031(3) 0.8703(2) 0.0490(7) Uani 1 1 d . . . C12 C 0.6722(4) 0.2119(2) 0.7815(2) 0.0465(6) Uani 1 1 d . . . C11 C 0.7297(4) 0.1111(3) 0.8426(2) 0.0492(7) Uani 1 1 d . . . C14 C 0.3466(4) 0.1945(2) 0.6811(2) 0.0484(7) Uani 1 1 d . . . O6 O 0.7836(5) 0.4477(3) 1.0216(2) 0.1195(12) Uani 1 1 d . . . C15 C 0.3700(4) 0.3120(3) 0.6258(2) 0.0570(7) Uani 1 1 d . . . C9 C 0.3866(3) 0.0473(2) 0.7790(2) 0.0443(6) Uani 1 1 d . . . C23 C 0.7505(4) 0.2319(3) 0.6826(2) 0.0531(7) Uani 1 1 d . . . C27 C 0.6929(4) 0.3393(3) 0.9565(2) 0.0576(7) Uani 1 1 d . . . N4 N 1.0536(4) 0.1499(3) 0.9090(3) 0.0789(8) Uani 1 1 d . . . C24 C 0.7495(5) 0.1290(3) 0.5164(2) 0.0648(8) Uani 1 1 d . . . H24A H 0.7232 0.0412 0.4877 0.078 Uiso 1 1 calc R . . H24B H 0.8743 0.1707 0.5420 0.078 Uiso 1 1 calc R . . C4 C -0.2183(5) -0.2929(3) 0.7594(3) 0.0776(10) Uani 1 1 d . . . H4 H -0.3151 -0.3614 0.7642 0.093 Uiso 1 1 calc R . . C2 C 0.0787(5) -0.1591(3) 0.8324(3) 0.0659(8) Uani 1 1 d . . . H2 H 0.1817 -0.1377 0.8874 0.079 Uiso 1 1 calc R . . C5 C -0.2271(5) -0.2199(4) 0.6725(4) 0.0856(11) Uani 1 1 d . . . H5 H -0.3309 -0.2402 0.6184 0.103 Uiso 1 1 calc R . . C6 C -0.0849(4) -0.1185(3) 0.6654(3) 0.0722(9) Uani 1 1 d . . . H6 H -0.0924 -0.0707 0.6067 0.087 Uiso 1 1 calc R . . C3 C -0.0637(5) -0.2617(3) 0.8377(3) 0.0730(9) Uani 1 1 d . . . H3 H -0.0551 -0.3109 0.8954 0.088 Uiso 1 1 calc R . . C25 C 0.6793(7) 0.1972(4) 0.4288(3) 0.0985(14) Uani 1 1 d . . . H25A H 0.7302 0.1964 0.3696 0.148 Uiso 1 1 calc R . . H25B H 0.7063 0.2843 0.4572 0.148 Uiso 1 1 calc R . . H25C H 0.5559 0.1550 0.4028 0.148 Uiso 1 1 calc R . . C7 C 0.2286(6) 0.4370(4) 0.5220(4) 0.1030(15) Uani 1 1 d . . . H7A H 0.1133 0.4327 0.4869 0.155 Uiso 1 1 calc R . . H7B H 0.2921 0.4435 0.4685 0.155 Uiso 1 1 calc R . . H7C H 0.2856 0.5110 0.5757 0.155 Uiso 1 1 calc R . . C28 C 0.7672(9) 0.4478(6) 1.1437(6) 0.157(3) Uani 1 1 d . . . H28A H 0.7200 0.3619 1.1634 0.189 Uiso 1 1 calc R . . H28B H 0.8762 0.4962 1.1968 0.189 Uiso 1 1 calc R . . C29 C 0.6563(13) 0.5073(10) 1.1295(8) 0.216(4) Uani 1 1 d . . . H29A H 0.6292 0.5183 1.1970 0.323 Uiso 1 1 calc R . . H29B H 0.5524 0.4572 1.0748 0.323 Uiso 1 1 calc R . . H29C H 0.7064 0.5897 1.1063 0.323 Uiso 1 1 calc R . . H31 H 0.603(4) -0.138(3) 0.945(2) 0.043(8) Uiso 1 1 d . . . H30 H 0.65(3) -0.464(19) 0.851(16) 0.55(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O3 0.0476(12) 0.0456(10) 0.0615(11) 0.0209(8) 0.0153(9) 0.0153(9) C8 0.054(2) 0.0568(17) 0.0599(17) 0.0115(13) 0.0179(14) 0.0182(15) N2 0.0552(15) 0.0466(12) 0.0535(13) 0.0149(10) 0.0128(11) 0.0188(12) O10 0.0736(15) 0.0575(12) 0.0547(11) 0.0013(9) 0.0278(10) 0.0113(11) N1 0.0462(13) 0.0389(11) 0.0520(12) 0.0117(9) 0.0133(10) 0.0148(10) O2 0.0763(16) 0.0629(13) 0.0887(16) 0.0387(12) 0.0191(13) 0.0300(13) O1 0.0738(18) 0.0691(15) 0.0949(17) 0.0394(13) 0.0154(13) 0.0080(14) O5 0.0871(18) 0.0740(15) 0.0663(14) 0.0025(11) 0.0376(13) 0.0017(14) O11 0.0799(16) 0.0661(14) 0.0707(13) -0.0010(11) 0.0396(12) -0.0058(13) C13 0.0476(16) 0.0389(13) 0.0438(13) 0.0079(10) 0.0107(11) 0.0113(12) N3 0.068(2) 0.0606(17) 0.0819(19) 0.0345(15) 0.0258(15) 0.0278(16) C26 0.0549(17) 0.0452(14) 0.0532(15) 0.0066(12) 0.0150(13) 0.0129(13) C1 0.0493(17) 0.0371(13) 0.0589(16) 0.0053(11) 0.0163(13) 0.0132(12) C10 0.0472(17) 0.0496(15) 0.0536(15) 0.0082(12) 0.0173(12) 0.0192(14) C12 0.0492(16) 0.0440(14) 0.0465(14) 0.0102(11) 0.0159(12) 0.0148(13) C11 0.0475(17) 0.0501(15) 0.0510(14) 0.0100(12) 0.0162(12) 0.0167(14) C14 0.0552(18) 0.0414(14) 0.0485(14) 0.0098(11) 0.0167(12) 0.0154(13) O6 0.154(3) 0.0822(17) 0.0938(18) -0.0309(15) 0.0794(19) -0.0209(19) C15 0.062(2) 0.0472(16) 0.0560(16) 0.0135(12) 0.0117(14) 0.0148(15) C9 0.0450(16) 0.0426(14) 0.0456(13) 0.0097(10) 0.0125(11) 0.0159(12) C23 0.0560(18) 0.0479(15) 0.0526(15) 0.0096(12) 0.0199(13) 0.0116(14) C27 0.064(2) 0.0510(16) 0.0556(16) 0.0048(13) 0.0209(15) 0.0150(15) N4 0.0576(19) 0.093(2) 0.089(2) 0.0164(17) 0.0197(15) 0.0310(17) C24 0.077(2) 0.0615(18) 0.0604(17) 0.0036(14) 0.0244(16) 0.0261(17) C4 0.058(2) 0.059(2) 0.107(3) 0.0104(19) 0.032(2) 0.0048(17) C2 0.063(2) 0.0631(19) 0.0592(17) 0.0164(14) 0.0142(15) 0.0085(16) C5 0.051(2) 0.078(2) 0.108(3) 0.015(2) 0.0044(19) 0.0100(19) C6 0.056(2) 0.069(2) 0.084(2) 0.0230(17) 0.0084(17) 0.0195(17) C3 0.075(2) 0.0564(18) 0.077(2) 0.0181(16) 0.0277(19) 0.0060(17) C25 0.150(4) 0.100(3) 0.073(2) 0.018(2) 0.034(3) 0.074(3) C7 0.120(4) 0.069(2) 0.124(3) 0.053(2) 0.026(3) 0.041(3) C28 0.118(5) 0.122(4) 0.187(6) -0.067(4) 0.039(5) -0.006(4) C29 0.237(11) 0.251(11) 0.214(9) 0.084(8) 0.103(8) 0.123(10) _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 O3 C9 1.360(3) . ? O3 C10 1.377(4) . ? C8 N4 1.142(4) . ? C8 C11 1.421(4) . ? N2 C14 1.326(4) . ? N2 N1 1.359(3) . ? O10 C23 1.331(3) . ? O10 C24 1.469(4) . ? N1 C9 1.356(4) . ? N1 C1 1.423(4) . ? O2 C15 1.323(4) . ? O2 C7 1.455(4) . ? O1 C15 1.189(4) . ? O5 C27 1.188(4) . ? O11 C23 1.185(3) . ? C13 C9 1.352(4) . ? C13 C14 1.419(4) . ? C13 C12 1.492(4) . ? N3 C10 1.340(3) . ? C26 C27 1.487(4) . ? C26 C12 1.546(4) . ? C1 C6 1.378(4) . ? C1 C2 1.381(4) . ? C10 C11 1.349(4) . ? C12 C11 1.531(3) . ? C12 C23 1.552(4) . ? C14 C15 1.479(4) . ? O6 C27 1.323(4) . ? O6 C28 1.595(8) . ? C24 C25 1.485(4) . ? C4 C3 1.370(5) . ? C4 C5 1.390(5) . ? C2 C3 1.372(5) . ? C5 C6 1.371(5) . ? C28 C29 1.315(9) . ? 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 C9 O3 C10 114.0(2) . . ? N4 C8 C11 178.1(4) . . ? C14 N2 N1 105.3(2) . . ? C23 O10 C24 116.7(2) . . ? C9 N1 N2 109.1(2) . . ? C9 N1 C1 131.2(2) . . ? N2 N1 C1 119.7(2) . . ? C15 O2 C7 116.9(3) . . ? C9 C13 C14 102.0(2) . . ? C9 C13 C12 122.2(2) . . ? C14 C13 C12 135.7(2) . . ? C27 C26 C12 114.7(2) . . ? C6 C1 C2 119.6(3) . . ? C6 C1 N1 118.7(2) . . ? C2 C1 N1 121.7(3) . . ? N3 C10 C11 127.1(3) . . ? N3 C10 O3 109.9(3) . . ? C11 C10 O3 123.0(2) . . ? C13 C12 C11 106.3(2) . . ? C13 C12 C26 113.2(2) . . ? C11 C12 C26 111.0(2) . . ? C13 C12 C23 112.0(2) . . ? C11 C12 C23 106.8(2) . . ? C26 C12 C23 107.3(2) . . ? C10 C11 C8 115.9(2) . . ? C10 C11 C12 125.7(3) . . ? C8 C11 C12 118.3(3) . . ? N2 C14 C13 112.6(2) . . ? N2 C14 C15 120.5(2) . . ? C13 C14 C15 126.8(3) . . ? C27 O6 C28 116.2(3) . . ? O1 C15 O2 125.1(3) . . ? O1 C15 C14 122.5(3) . . ? O2 C15 C14 112.3(3) . . ? C13 C9 N1 110.9(2) . . ? C13 C9 O3 128.1(2) . . ? N1 C9 O3 120.9(2) . . ? O11 C23 O10 124.4(3) . . ? O11 C23 C12 124.4(3) . . ? O10 C23 C12 111.1(2) . . ? O5 C27 O6 122.3(3) . . ? O5 C27 C26 126.9(3) . . ? O6 C27 C26 110.9(3) . . ? O10 C24 C25 110.1(3) . . ? C3 C4 C5 118.5(3) . . ? C3 C2 C1 120.0(3) . . ? C6 C5 C4 120.9(3) . . ? C5 C6 C1 119.8(3) . . ? C4 C3 C2 121.1(3) . . ? C29 C28 O6 96.1(7) . . ? _diffrn_measured_fraction_theta_max 0.863 _diffrn_reflns_theta_full 26.73 _diffrn_measured_fraction_theta_full 1.126 _refine_diff_density_max 0.424 _refine_diff_density_min -0.479 _refine_diff_density_rms 0.075 _database_code_depnum_ccdc_archive 'CCDC 968630'