# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _chemical_name_systematic ; ? ; _chemical_name_common 'fluorescein:acridine cocrystal' _chemical_formula_moiety '(C20 H12 O5), (C13 H9 N1)2' _chemical_formula_structural '(C20 H12 O5), (C13 H9 N1)2' _chemical_formula_sum 'C46 H30 N2 O5' _chemical_formula_weight 690.75 _chemical_melting_point ? #============================================================================== # 6. POWDER SPECIMEN AND CRYSTAL DATA _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'C m c 21' _space_group_name_Hall 'C 2c -2' loop_ _symmetry_equiv_pos_as_xyz '-x, -y, z+1/2' '-x, y, z' 'x, -y, z+1/2' 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' 'x+1/2, y+1/2, z' _cell_length_a 25.2998(38) _cell_length_b 16.8440(27) _cell_length_c 7.88987(81) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3362.27(82) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _exptl_crystal_density_diffrn 1.3646(3) _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _cell_special_details ; ? ; # The next three fields give the specimen dimensions in mm. The equatorial # plane contains the incident and diffracted beam. _pd_spec_size_axial 14 # perpendicular to # equatorial plane _pd_spec_size_equat 10 # parallel to # scattering vector # in transmission _pd_spec_size_thick 0.5 # parallel to # scattering vector # in reflection # The next five fields are character fields that describe the specimen. _pd_spec_mounting # This field should be # used to give details of the # container. ; ? ; _pd_spec_mount_mode reflection _pd_spec_shape flat_sheet _pd_char_colour white #============================================================================== # 7. EXPERIMENTAL DATA _diffrn_ambient_temperature 293 _diffrn_source 'sealed X-ray tube' _diffrn_source_target Cu _diffrn_source_type ? _diffrn_radiation_type 'Cu K\a' _diffrn_measurement_device_type "Panalytical X'pert Powder" _diffrn_detector ? _diffrn_detector_type X'Celerator _pd_meas_scan_method cont _pd_meas_special_details ; ? ; # The following six items are used for angular dispersive measurements only. _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_monochromator none # The following four items give details of the measured (not processed) # powder pattern. Angles are in degrees. _pd_meas_number_of_points 1725 _pd_meas_2theta_range_min 3.0152 _pd_meas_2theta_range_max 59.9402 _pd_meas_2theta_range_inc 0.033 #============================================================================== # 8. REFINEMENT DATA # Use the next field to give any special details about the fitting of the # powder pattern. _pd_proc_ls_special_details ; An impurity of fluorescein (NUKCOL) was found. The weight fraction of the impurity was determined by Quantitative Phase Analysis at 5%. ; # The next three items are given as text. _pd_proc_ls_profile_function pseudo-Voigt _pd_proc_ls_background_function 'Chebyshev polynomial' _pd_proc_ls_pref_orient_corr none _pd_proc_ls_prof_R_factor 0.044 _pd_proc_ls_prof_wR_factor 0.056 _pd_proc_ls_prof_wR_expected 0.023 _refine_ls_R_I_factor 0.018 _refine_ls_weighting_scheme calc _refine_ls_number_parameters 42 _refine_ls_number_restraints 0 _refine_ls_number_constraints 123 # The following item is the same as CHI, the square root of 'CHI squared' _refine_ls_goodness_of_fit_all 2.421 _computing_data_collection "X'Pert Data Collector (Panalytical)" _computing_cell_refinement 'DICVOL 06 (Louer et al)' _computing_structure_solution 'TOPAS Academic (Coelho 2007)' _computing_structure_refinement 'TOPAS Academic (Coelho 2007)' #============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_B_iso_or_equiv _atom_site_occupancy _atom_site_symmetry_multiplicity C1 C 0.5 1.1964(10) 0.8171(61) 0.18(33) 1 2 O1 O 0.5 1.2732(16) 0.7152(54) 0.18(33) 1 2 C2 C 0.5 1.3377(10) 0.8187(54) 0.18(33) 1 2 C3 C 0.5 1.31074(62) 0.9970(53) 0.18(33) 1 2 C4 C 0.5 1.3551(13) 1.1442(55) 0.18(33) 1 2 C5 C 0.5 1.3147(21) 1.2956(53) 0.18(33) 1 2 C6 C 0.5 1.2314(21) 1.2969(57) 0.18(33) 1 2 C7 C 0.5 1.1876(13) 1.1499(62) 0.18(33) 1 2 C8 C 0.5 1.22833(63) 0.9978(57) 0.18(33) 1 2 O2 O 0.5 1.4050(13) 0.7636(60) 0.18(33) 1 2 O4 O 0.5 1.0427(14) 0.6227(53) 0.18(33) 1 2 C14 C 0.54598(22) 1.0742(12) 0.6901(48) 0.18(33) 1 1 C9 C 0.54586(61) 1.1385(13) 0.8009(47) 0.18(33) 1 1 C10 C 0.59502(81) 1.1646(12) 0.8599(48) 0.18(33) 1 1 C11 C 0.64185(63) 1.1295(11) 0.8113(52) 0.18(33) 1 1 C12 C 0.64063(23) 1.0663(11) 0.6959(53) 0.18(33) 1 1 C13 C 0.592332(45) 1.0379(11) 0.6370(50) 0.18(33) 1 1 O3 O 0.685436(66) 1.0302(11) 0.6399(61) 0.18(33) 1 1 H1 H 0.5 1.4104(12) 1.1435(61) 0.18(33) 1 2 H2 H 0.5 1.3426(27) 1.3973(54) 0.18(33) 1 2 H3 H 0.5 1.2059(27) 1.4014(60) 0.18(33) 1 2 H4 H 0.5 1.1323(13) 1.1503(71) 0.18(33) 1 2 H5 H 0.5953(11) 1.2066(13) 0.9365(49) 0.18(33) 1 1 H6 H 0.67406(76) 1.1485(12) 0.8509(57) 0.18(33) 1 1 H8 H 0.59094(23) 0.9950(12) 0.5629(52) 0.18(33) 1 1 H7 H 0.71220(19) 1.0520(12) 0.6855(66) 0.18(33) 1 1 N1 N 0.78361(31) 1.09427(56) 0.7815(50) 0.18(33) 1 1 C15 C 0.81395(26) 1.03939(56) 0.8590(50) 0.18(33) 1 1 C16 C 0.79862(36) 0.95802(56) 0.8483(49) 0.18(33) 1 1 C17 C 0.82839(46) 0.90022(60) 0.9219(49) 0.18(33) 1 1 C18 C 0.87509(45) 0.91951(75) 1.0123(50) 0.18(33) 1 1 C19 C 0.89069(35) 0.99638(81) 1.0277(51) 0.18(33) 1 1 C20 C 0.86103(26) 1.05892(68) 0.9511(51) 0.18(33) 1 1 C21 C 0.87620(32) 1.13820(72) 0.9595(53) 0.18(33) 1 1 C22 C 0.84626(39) 1.19572(61) 0.8771(53) 0.18(33) 1 1 C23 C 0.86076(56) 1.27769(65) 0.8733(57) 0.18(33) 1 1 C24 C 0.83027(68) 1.33101(57) 0.7890(57) 0.18(33) 1 1 C25 C 0.78330(67) 1.30648(57) 0.7064(55) 0.18(33) 1 1 C26 C 0.76774(53) 1.22919(59) 0.7066(53) 0.18(33) 1 1 C27 C 0.79929(38) 1.17060(55) 0.7898(52) 0.18(33) 1 1 H9 H 0.76765(43) 0.94357(58) 0.7876(50) 0.18(33) 1 1 H10 H 0.81779(57) 0.84625(59) 0.9139(50) 0.18(33) 1 1 H11 H 0.89554(55) 0.87863(85) 1.0631(50) 0.18(33) 1 1 H12 H 0.92201(41) 1.00897(95) 1.0884(53) 0.18(33) 1 1 H13 H 0.90754(39) 1.15269(86) 1.0181(55) 0.18(33) 1 1 H14 H 0.89207(60) 1.29496(76) 0.9286(59) 0.18(33) 1 1 H15 H 0.84003(80) 1.38546(59) 0.7867(60) 0.18(33) 1 1 H16 H 0.76221(78) 1.34420(62) 0.6477(56) 0.18(33) 1 1 H17 H 0.73610(56) 1.21406(68) 0.6504(53) 0.18(33) 1 1 #============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C9 C10 1.40(3) . . yes C10 C11 1.38(3) . . yes C11 C12 1.40(4) . . yes C12 C13 1.39(2) . . yes C14 C13 1.39(2) . . yes O4 C14 1.38(3) . . yes N1 C15 1.35(3) . . yes C15 C16 1.43(1) . . yes C16 C17 1.36(3) . . yes C17 C18 1.42(3) . . yes C18 C19 1.36(2) . . yes O1 C2 1.36(4) . . yes C15 C20 1.43(3) . . yes C19 C20 1.43(3) . . yes C20 C21 1.39(2) . . yes C21 C22 1.39(3) . . yes C22 C23 1.43(2) . . yes C23 C24 1.36(3) . . yes C24 C25 1.42(4) . . yes C25 C26 1.36(1) . . yes C22 C27 1.44(3) . . yes C26 C27 1.43(3) . . yes N1 C27 1.35(1) . . yes C2 C3 1.48(6) . . yes C3 C4 1.38(5) . . yes C4 C5 1.37(6) . . yes C5 C6 1.40(5) . . yes C6 C7 1.37(6) . . yes C1 C8 1.52(6) . . yes C3 C8 1.39(1) . . yes C7 C8 1.38(6) . . yes C1 C9 1.52(2) . 455 yes C14 C9 1.39(4) . . yes C1 O1 1.52(4) . . yes C2 O2 1.21(3) . . yes C12 O3 1.36(2) . . yes C4 H1 0.93(3) . . yes C17 H10 0.95(1) . . yes C18 H11 0.95(3) . . yes C19 H12 0.95(3) . . yes C21 H13 0.95(3) . . yes C23 H14 0.95(3) . . yes C24 H15 0.95(2) . . yes C25 H16 0.95(3) . . yes C26 H17 0.95(3) . . yes C5 H2 0.93(6) . . yes C6 H3 0.93(6) . . yes C7 H4 0.93(3) . . yes C10 H5 0.93(4) . . yes C11 H6 0.93(3) . . yes O3 H7 0.85(3) . . yes C13 H8 0.93(4) . . yes C16 H9 0.95(3) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C2 111(3) . . . yes C1 C8 C3 110(2) . . . yes C1 C8 C7 130(3) . . . yes C1 C9 C14 124(2) 455 . . yes C1 C9 C10 117(2) 455 455 . yes C10 C11 C12 119(2) . . . yes C10 C11 H6 121(3) . . . yes C10 C11 C12 119(2) . . . yes C11 C10 H5 120(3) . . . yes C11 C12 C13 120(2) . . . yes C11 C12 O3 122(2) . . . yes C12 C11 H6 120(3) . . . yes C12 C13 H8 121(2) . . . yes C12 O3 H7 109(3) . . . yes C13 C12 O3 118(2) . . . yes C14 C13 C12 119(2) . . . yes C14 C13 H8 120(2) . . . yes C14 C9 C10 117(2) . . . yes C14 O4 C14 114(3) . . . yes C15 C16 C17 121(2) . . . yes C15 C16 H9 120(2) . . . yes C15 C20 C19 119(2) . . . yes C15 C20 C21 118(2) . . . yes C15 N1 C27 118(2) . . . yes C16 C15 C20 118(2) . . . yes C16 C17 C18 121(2) . . . yes C16 C17 H10 120(2) . . . yes C17 C16 H9 119(2) . . . yes C17 C18 C19 120(2) . . . yes C17 C18 H11 120(2) . . . yes C18 C17 H10 119(2) . . . yes C18 C19 C20 121(2) . . . yes C18 C19 H12 120(2) . . . yes C19 C18 H11 120(2) . . . yes C19 C20 C21 123(2) . . . yes C2 C3 C4 129(3) . . . yes C2 C3 C8 108(2) . . . yes C20 C19 H12 119(2) . . . yes C20 C21 C22 120(2) . . . yes C20 C21 H13 120(2) . . . yes C21 C22 C23 123(2) . . . yes C21 C22 C27 118(2) . . . yes C22 C21 H13 120(2) . . . yes C22 C23 C24 120(2) . . . yes C22 C23 H14 120(3) . . . yes C22 C27 C26 119(2) . . . yes C23 C22 C27 119(2) . . . yes C23 C24 C25 121(2) . . . yes C23 C24 H15 120(3) . . . yes C24 C23 H14 120(3) . . . yes C24 C25 C26 121(2) . . . yes C24 C25 H16 120(3) . . . yes C25 C24 H15 119(3) . . . yes C25 C26 C27 120(2) . . . yes C25 C26 H17 120(3) . . . yes C26 C25 H16 119(3) . . . yes C27 C26 H17 120(2) . . . yes C3 C2 O2 129(3) . . . yes C3 C4 C5 118(3) . . . yes C3 C4 H1 122(4) . . . yes C3 C8 C7 120(3) . . . yes C4 C3 C8 122(3) . . . yes C4 C5 C6 120(3) . . . yes C4 C5 H2 120(5) . . . yes C5 C4 H1 120(4) . . . yes C5 C6 C7 122(4) . . . yes C5 C6 H3 118(5) . . . yes C6 C5 H2 120(5) . . . yes C6 C7 C8 118(3) . . . yes C6 C7 H4 122(4) . . . yes C7 C6 H3 120(5) . . . yes C8 C1 C9 108(2) 455 455 . yes C8 C7 H4 120(4) . . . yes C9 C1 C9 99(2) . . . yes C9 C10 C11 122(2) . . . yes C9 C10 H5 118(3) . . . yes C9 C14 C13 122(2) . . . yes N1 C15 C16 118(2) . . . yes N1 C27 C22 123(2) . . . yes N1 C27 C26 118(2) . . . yes O1 C1 C8 101(3) . . . yes O1 C1 C9 120(3) 455 455 . yes O1 C2 C3 109(3) . . . yes O1 C2 O2 122(3) . . . yes O4 C14 C9 123(2) . . . yes O4 C14 C13 115(2) . . . yes O4 C14 C9 123(2) . . . yes _database_code_depnum_ccdc_archive 'CCDC 908178' ####################################################################### # # 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_2 # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common 'fluorescein:phenantridine cocrystal' _chemical_formula_moiety '(C20 H12 O5), (C13 H9 N1)2' _chemical_formula_structural '(C20 H12 O5), (C13 H9 N1)2' _chemical_formula_sum 'C46 H30 N2 O5' _chemical_formula_weight 690.75 _chemical_melting_point ? #============================================================================== # 6. POWDER SPECIMEN AND CRYSTAL DATA _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'C m c 21' _space_group_name_Hall 'C 2c -2' loop_ _symmetry_equiv_pos_as_xyz '-x, -y, z+1/2' '-x, y, z' 'x, -y, z+1/2' 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' 'x+1/2, y+1/2, z' _cell_length_a 27.7697(34) _cell_length_b 15.4238(20) _cell_length_c 7.98164(85) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3418.62(71) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _exptl_crystal_density_diffrn 1.34211(28) _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _cell_special_details ; ? ; # The next three fields give the specimen dimensions in mm. The equatorial # plane contains the incident and diffracted beam. _pd_spec_size_axial 14 # perpendicular to # equatorial plane _pd_spec_size_equat 10 # parallel to # scattering vector # in transmission _pd_spec_size_thick 0.5 # parallel to # scattering vector # in reflection # The next five fields are character fields that describe the specimen. _pd_spec_mounting # This field should be # used to give details of the # container. ; ? ; _pd_spec_mount_mode reflection _pd_spec_shape flat_sheet _pd_char_colour white #============================================================================== # 7. EXPERIMENTAL DATA _diffrn_ambient_temperature 293 _diffrn_source 'sealed X-ray tube' _diffrn_source_target Cu _diffrn_source_type ? _diffrn_radiation_type 'Cu K\a' _diffrn_measurement_device_type "Panalytical X'pert Powder" _diffrn_detector ? _diffrn_detector_type X'Celerator _pd_meas_scan_method cont _pd_meas_special_details ; ? ; # The following six items are used for angular dispersive measurements only. _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_monochromator none # The following four items give details of the measured (not processed) # powder pattern. Angles are in degrees. _pd_meas_number_of_points 1272 _pd_meas_2theta_range_min 3.0212 _pd_meas_2theta_range_max 44.9642 _pd_meas_2theta_range_inc 0.033 #============================================================================== # 8. REFINEMENT DATA # Use the next field to give any special details about the fitting of the # powder pattern. _pd_proc_ls_special_details ; ; # The next three items are given as text. _pd_proc_ls_profile_function pseudo-Voigt _pd_proc_ls_background_function 'Chebyshev polynomial' _pd_proc_ls_pref_orient_corr none _pd_proc_ls_prof_R_factor 0.040 _pd_proc_ls_prof_wR_factor 0.052 _pd_proc_ls_prof_wR_expected 0.012 _refine_ls_R_I_factor 0.023 _refine_ls_weighting_scheme calc _refine_ls_number_parameters 36 _refine_ls_number_restraints 0 _refine_ls_number_constraints 129 # The following item is the same as CHI, the square root of 'CHI squared' _refine_ls_goodness_of_fit_all 4.176 _computing_data_collection "X'Pert Data Collector (Panalytical)" _computing_cell_refinement 'DICVOL 06 (Louer et al)' _computing_structure_solution 'TOPAS Academic (Coelho 2007)' _computing_structure_refinement 'TOPAS Academic (Coelho 2007)' #============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_B_iso_or_equiv _atom_site_occupancy _atom_site_symmetry_multiplicity C1 C 0.5 -0.7982(10) -0.3730(31) 0.24(26) 1 2 O1 O 0.5 -0.7087(13) -0.4538(22) 0.24(26) 1 2 C2 C 0.5 -0.64509(92) -0.3360(18) 0.24(26) 1 2 C3 C 0.5 -0.68519(60) -0.1677(20) 0.24(26) 1 2 C4 C 0.5 -0.64598(83) -0.0121(19) 0.24(26) 1 2 C5 C 0.5 -0.6991(13) 0.1265(21) 0.24(26) 1 2 C6 C 0.5 -0.7895(12) 0.1068(30) 0.24(26) 1 2 C7 C 0.5 -0.82804(74) -0.0485(35) 0.24(26) 1 2 C8 C 0.5 -0.77459(61) -0.1876(29) 0.24(26) 1 2 O2 O 0.5 -0.5688(10) -0.3733(20) 0.24(26) 1 2 H1 H 0.5 -0.58608(87) 0.0011(19) 0.24(26) 1 2 H2 H 0.5 -0.6750(17) 0.2333(20) 0.24(26) 1 2 H3 H 0.5 -0.8235(15) 0.2030(35) 0.24(26) 1 2 H4 H 0.5 -0.88794(71) -0.0619(43) 0.24(26) 1 2 O4 O 0.5 -0.94952(72) -0.6148(23) 0.24(26) 1 2 C14 C 0.54121(15) -0.91751(46) -0.5391(16) 0.24(26) 1 1 C9 C 0.53968(42) -0.85885(53) -0.4066(17) 0.24(26) 1 1 C10 C 0.58390(56) -0.83156(59) -0.3413(18) 0.24(26) 1 1 C11 C 0.62734(43) -0.86101(47) -0.4027(21) 0.24(26) 1 1 C12 C 0.62754(17) -0.92193(35) -0.5329(18) 0.24(26) 1 1 C13 C 0.584203(27) -0.94929(43) -0.6028(14) 0.24(26) 1 1 O3 O 0.669086(44) -0.95504(54) -0.5965(25) 0.24(26) 1 1 H5 H 0.58330(74) -0.79112(82) -0.2549(21) 0.24(26) 1 1 H6 H 0.65624(53) -0.84262(65) -0.3557(28) 0.24(26) 1 1 H8 H 0.58389(16) -0.98843(64) -0.6914(15) 0.24(26) 1 1 H7 H 0.69300(14) -0.93306(60) -0.5453(30) 0.24(26) 1 1 N1 N 0.75168(17) -0.90347(92) -0.4801(11) 0.24(26) 1 1 C15 C 0.76894(31) -0.97300(75) -0.4106(11) 0.24(26) 1 1 C16 C 0.81390(36) -0.97665(49) -0.3241(11) 0.24(26) 1 1 C17 C 0.83019(57) -1.05415(49) -0.2507(12) 0.24(26) 1 1 C18 C 0.87357(63) -1.05638(68) -0.1686(13) 0.24(26) 1 1 C19 C 0.90131(47) -0.98182(85) -0.1598(15) 0.24(26) 1 1 C20 C 0.88615(28) -0.90508(69) -0.2308(16) 0.24(26) 1 1 C21 C 0.84174(22) -0.90101(46) -0.3137(14) 0.24(26) 1 1 C22 C 0.82306(19) -0.82323(47) -0.3915(15) 0.24(26) 1 1 C23 C 0.84699(35) -0.74304(45) -0.3899(20) 0.24(26) 1 1 C24 C 0.82724(54) -0.67146(49) -0.4639(22) 0.24(26) 1 1 C27 C 0.77819(20) -0.82744(73) -0.4723(13) 0.24(26) 1 1 C26 C 0.75848(39) -0.75330(93) -0.5484(15) 0.24(26) 1 1 C25 C 0.78311(57) -0.67614(76) -0.5453(19) 0.24(26) 1 1 H9 H 0.74949(42) -1.02348(89) -0.4193(13) 0.24(26) 1 1 H10 H 0.81094(69) -1.10495(51) -0.2573(14) 0.24(26) 1 1 H11 H 0.88476(78) -1.10856(80) -0.1187(14) 0.24(26) 1 1 H12 H 0.93144(51) -0.9845(11) -0.1036(17) 0.24(26) 1 1 H13 H 0.90585(23) -0.85487(82) -0.2233(19) 0.24(26) 1 1 H14 H 0.87727(35) -0.73766(56) -0.3355(22) 0.24(26) 1 1 H15 H 0.84396(67) -0.61774(46) -0.4616(26) 0.24(26) 1 1 H16 H 0.76983(71) -0.62585(90) -0.5962(21) 0.24(26) 1 1 H17 H 0.72828(41) -0.7570(12) -0.6039(14) 0.24(26) 1 1 #============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.52(3) . . yes C1 C8 1.52(3) . . yes C1 C9 1.47(2) . . yes O1 C2 1.36(2) . . yes C2 C3 1.48(2) . . yes C2 O2 1.21(2) . . yes C3 C4 1.38(2) . . yes C3 C8 1.39(1) . . yes C4 C5 1.38(2) . . yes C4 H1 0.93(2) . . yes C5 C6 1.40(3) . . yes C5 H2 0.93(2) . . yes C6 C7 1.37(3) . . yes C6 H3 0.93(3) . . yes C7 C8 1.38(3) . . yes C7 H4 0.93(2) . . yes O4 C14 1.39(1) . . yes C14 C9 1.39(2) . . yes C14 C13 1.387(8) . . yes C9 C10 1.40(2) . . yes C10 C11 1.38(2) . . yes C10 H5 0.93(2) . . yes C11 C12 1.40(2) . . yes C11 H6 0.93(2) . . yes C12 C13 1.392(9) . . yes C12 O3 1.36(1) . . yes C13 H8 0.93(1) . . yes O3 H7 0.85(2) . . yes N1 C15 1.30(2) . . yes N1 C27 1.39(2) . . yes C15 C16 1.43(1) . . yes C15 H9 0.95(2) . . yes C16 C17 1.41(1) . . yes C16 C21 1.40(1) . . yes C17 C18 1.37(2) . . yes C17 H10 0.95(2) . . yes C18 C19 1.39(2) . . yes C18 H11 0.95(2) . . yes C19 C20 1.38(2) . . yes C19 H12 0.95(2) . . yes C20 C21 1.40(1) . . yes C20 H13 0.95(1) . . yes C21 C22 1.45(1) . . yes C22 C23 1.40(1) . . yes C22 C27 1.40(1) . . yes C23 C24 1.37(2) . . yes C23 H14 0.95(2) . . yes C24 C25 1.39(2) . . yes C24 H15 0.95(1) . . yes C27 C26 1.41(2) . . yes C26 C25 1.37(2) . . yes C26 H17 0.95(2) . . yes C25 H16 0.95(2) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C8 101(1) . . . yes O1 C1 C9 120(2) . . . yes O1 C1 C9 120(2) . . . yes C8 C1 C9 109(1) . . . yes C8 C1 C9 109(1) . . . yes C9 C1 C9 97(1) . . . yes C1 O1 C2 111(2) . . . yes O1 C2 C3 109(1) . . . yes O1 C2 O2 122(2) . . . yes C3 C2 O2 129(1) . . . yes C2 C3 C4 129(1) . . . yes C2 C3 C8 108(1) . . . yes C4 C3 C8 123(1) . . . yes C3 C4 C5 118(1) . . . yes C3 C4 H1 122(2) . . . yes C5 C4 H1 120(2) . . . yes C4 C5 C6 120(2) . . . yes C4 C5 H2 120(2) . . . yes C6 C5 H2 120(2) . . . yes C5 C6 C7 122(2) . . . yes C5 C6 H3 118(3) . . . yes C7 C6 H3 120(3) . . . yes C6 C7 C8 118(2) . . . yes C6 C7 H4 122(2) . . . yes C8 C7 H4 120(2) . . . yes C1 C8 C3 110(1) . . . yes C1 C8 C7 130(2) . . . yes C3 C8 C7 120(2) . . . yes C14 O4 C14 111(1) . . . yes O4 C14 C9 123(1) . . . yes O4 C14 C13 115.2(9) . . . yes C9 C14 C13 122.3(8) . . . yes C1 C9 C14 125(1) . . . yes C1 C9 C10 113(1) . . . yes C14 C9 C10 117(1) . . . yes C9 C10 C11 122(1) . . . yes C9 C10 H5 118(2) . . . yes C11 C10 H5 120(2) . . . yes C10 C11 C12 119(1) . . . yes C10 C11 H6 121(2) . . . yes C12 C11 H6 120(1) . . . yes C11 C12 C13 119.8(8) . . . yes C11 C12 O3 122.1(9) . . . yes C13 C12 O3 118.0(8) . . . yes C14 C13 C12 119.3(6) . . . yes C14 C13 H8 120.0(8) . . . yes C12 C13 H8 120.6(8) . . . yes C12 O3 H7 109(1) . . . yes O4 C14 C9 123(1) . . . yes O4 C14 C13 115.2(9) . . . yes C9 C14 C13 122.3(8) . . . yes C1 C9 C14 125(1) . . . yes C1 C9 C10 113(1) . . . yes C14 C9 C10 117(1) . . . yes C9 C10 C11 122(1) . . . yes C9 C10 H5 118(2) . . . yes C11 C10 H5 120(2) . . . yes C10 C11 C12 119(1) . . . yes C10 C11 H6 121(2) . . . yes C12 C11 H6 120(1) . . . yes C11 C12 C13 119.8(8) . . . yes C11 C12 O3 122.1(9) . . . yes C13 C12 O3 118.0(8) . . . yes C14 C13 C12 119.3(6) . . . yes C14 C13 H8 120.0(8) . . . yes C12 C13 H8 120.6(8) . . . yes C12 O3 H7 109(1) . . . yes C15 N1 C27 118.9(9) . . . yes N1 C15 C16 124.2(9) . . . yes N1 C15 H9 116(1) . . . yes C16 C15 H9 120(1) . . . yes C15 C16 C17 121.1(9) . . . yes C15 C16 C21 118.6(8) . . . yes C17 C16 C21 120.4(8) . . . yes C16 C17 C18 120(1) . . . yes C16 C17 H10 120(1) . . . yes C18 C17 H10 120(1) . . . yes C17 C18 C19 119(1) . . . yes C17 C18 H11 121(2) . . . yes C19 C18 H11 120(2) . . . yes C18 C19 C20 121(1) . . . yes C18 C19 H12 119(2) . . . yes C20 C19 H12 120(2) . . . yes C19 C20 C21 120(1) . . . yes C19 C20 H13 120(1) . . . yes C21 C20 H13 120(1) . . . yes C16 C21 C20 118.4(8) . . . yes C16 C21 C22 117.8(7) . . . yes C20 C21 C22 123.7(8) . . . yes C21 C22 C23 123.8(8) . . . yes C21 C22 C27 118.5(7) . . . yes C23 C22 C27 117.7(8) . . . yes C22 C23 C24 121(1) . . . yes C22 C23 H14 120(1) . . . yes C24 C23 H14 119(1) . . . yes C23 C24 C25 121(1) . . . yes C23 C24 H15 120(2) . . . yes C25 C24 H15 119(2) . . . yes N1 C27 C22 122.1(8) . . . yes N1 C27 C26 117.5(9) . . . yes C22 C27 C26 120.4(9) . . . yes C27 C26 C25 120(1) . . . yes C27 C26 H17 120(1) . . . yes C25 C26 H17 120(1) . . . yes C24 C25 C26 120(1) . . . yes C24 C25 H16 120(2) . . . yes C26 C25 H16 120(2) . . . yes _database_code_depnum_ccdc_archive 'CCDC 908179' ####################################################################### # # 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_3 # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common 'fluorescein:pyrazine cocrystal' _chemical_formula_moiety '(C20 H12 O5), (C4 H4 N2)' _chemical_formula_structural '(C20 H12 O5), (C4 H4 N2)' _chemical_formula_sum 'C24 H16 N2 O5' _chemical_formula_weight 412.40 _chemical_melting_point ? #============================================================================== # 6. POWDER SPECIMEN AND CRYSTAL DATA _space_group_crystal_system monoclinic _space_group_name_H-M_alt P21/c _space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz '-x, -y, -z' '-x, y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' 'x, y, z' _cell_length_a 7.81238(87) _cell_length_b 19.0241(17) _cell_length_c 12.7880(14) _cell_angle_alpha 90 _cell_angle_beta 91.1378(67) _cell_angle_gamma 90 _cell_volume 1900.22(34) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _exptl_crystal_density_diffrn 1.44150(3) _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _cell_special_details ; ? ; # The next three fields give the specimen dimensions in mm. The equatorial # plane contains the incident and diffracted beam. _pd_spec_size_axial 14 # perpendicular to # equatorial plane _pd_spec_size_equat 10 # parallel to # scattering vector # in transmission _pd_spec_size_thick 0.5 # parallel to # scattering vector # in reflection # The next five fields are character fields that describe the specimen. _pd_spec_mounting # This field should be # used to give details of the # container. ; ? ; _pd_spec_mount_mode reflection _pd_spec_shape flat_sheet _pd_char_colour white #============================================================================== # 7. EXPERIMENTAL DATA _diffrn_ambient_temperature 293 _diffrn_source 'sealed X-ray tube' _diffrn_source_target Cu _diffrn_source_type ? _diffrn_radiation_type 'Cu K\a' _diffrn_measurement_device_type "Panalytical X'pert Powder" _diffrn_detector ? _diffrn_detector_type X'Celerator _pd_meas_scan_method cont _pd_meas_special_details ; ? ; # The following six items are used for angular dispersive measurements only. _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_monochromator none # The following four items give details of the measured (not processed) # powder pattern. Angles are in degrees. _pd_meas_number_of_points 1725 _pd_meas_2theta_range_min 3.0152 _pd_meas_2theta_range_max 59.9402 _pd_meas_2theta_range_inc 0.033 #============================================================================== # 8. REFINEMENT DATA # Use the next field to give any special details about the fitting of the # powder pattern. _pd_proc_ls_special_details ; ? ; # The next three items are given as text. _pd_proc_ls_profile_function pseudo-Voigt _pd_proc_ls_background_function 'Chebyshev polynomial' _pd_proc_ls_pref_orient_corr none _pd_proc_ls_prof_R_factor 0.040 _pd_proc_ls_prof_wR_factor 0.052 _pd_proc_ls_prof_wR_expected 0.031 _refine_ls_R_I_factor 0.028 _refine_ls_weighting_scheme calc _refine_ls_number_parameters 39 _refine_ls_number_restraints 0 _refine_ls_number_constraints 132 # The following item is the same as CHI, the square root of 'CHI squared' _refine_ls_goodness_of_fit_all 1.692 _computing_data_collection "X'Pert Data Collector (Panalytical)" _computing_cell_refinement 'DICVOL 06 (Louer et al)' _computing_structure_solution 'TOPAS Academic (Coelho 2007)' _computing_structure_refinement 'TOPAS Academic (Coelho 2007)' #============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_symmetry_multiplicity _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_B_iso_or_equiv C1 C 1 0.96462(66) 0.04449(15) 0.77188(19) 1 3.25(20) O1 O 1 0.85638(92) 0.07202(19) 0.68027(27) 1 3.25(20) C2 C 1 0.9532(12) 0.08256(19) 0.59454(19) 1 3.25(20) C3 C 1 1.1327(11) 0.06343(16) 0.62003(22) 1 3.25(20) C4 C 1 1.2746(13) 0.06565(21) 0.55744(36) 1 3.25(20) C5 C 1 1.4287(12) 0.04466(23) 0.60109(54) 1 3.25(20) C6 C 1 1.43761(83) 0.02208(20) 0.70550(56) 1 3.25(20) C7 C 1 1.29573(67) 0.02000(15) 0.76736(39) 1 3.25(20) C8 C 1 1.14103(79) 0.04112(12) 0.72335(23) 1 3.25(20) O2 O 1 0.8923(15) 0.10439(25) 0.51282(24) 1 3.25(20) C9 C 1 0.94962(59) 0.09697(18) 0.85887(20) 1 3.25(20) C10 C 1 1.02542(73) 0.16343(16) 0.85289(23) 1 3.25(20) C11 C 1 1.00207(81) 0.21447(20) 0.92785(30) 1 3.25(20) C12 C 1 0.89580(83) 0.20023(28) 1.01223(35) 1 3.25(20) C13 C 1 0.82084(72) 0.13420(30) 1.02155(35) 1 3.25(20) C14 C 1 0.84876(55) 0.08389(25) 0.94525(29) 1 3.25(20) O4 O 1 0.76674(51) 0.02025(28) 0.96037(38) 1 3.25(20) C15 C 1 0.79310(46) -0.03384(24) 0.89001(38) 1 3.25(20) C16 C 1 0.71175(52) -0.09656(28) 0.91327(51) 1 3.25(20) C17 C 1 0.72850(62) -0.15366(25) 0.84618(55) 1 3.25(20) C18 C 1 0.83103(73) -0.14786(19) 0.75794(48) 1 3.25(20) C19 C 1 0.90870(72) -0.08448(16) 0.73678(35) 1 3.25(20) C20 C 1 0.89199(56) -0.02569(18) 0.80147(29) 1 3.25(20) O3 O 1 0.8643(10) 0.24878(33) 1.08752(44) 1 3.25(20) O5 O 1 0.64526(74) -0.21416(29) 0.87019(68) 1 3.25(20) H1 H 1 1.2689(15) 0.08061(25) 0.48822(35) 1 3.25(20) H2 H 1 1.5271(13) 0.04545(28) 0.56129(66) 1 3.25(20) H3 H 1 1.54369(76) 0.00824(24) 0.73261(69) 1 3.25(20) H4 H 1 1.30127(52) 0.00506(16) 0.83658(41) 1 3.25(20) H5 H 1 1.09567(83) 0.17226(13) 0.79651(24) 1 3.25(20) H6 H 1 1.05232(92) 0.25853(19) 0.92142(36) 1 3.25(20) H8 H 1 0.75269(82) 0.12366(35) 1.07826(42) 1 3.25(20) H9 H 1 0.64378(60) -0.10026(33) 0.97190(58) 1 3.25(20) H11 H 1 0.84507(87) -0.18581(19) 0.71309(52) 1 3.25(20) H12 H 1 0.96579(88) -0.08061(16) 0.67391(33) 1 3.25(20) H7a H 1 0.7976(11) 0.23131(38) 1.13235(47) 0.5 3.25(20) H7b H 1 0.8746(11) 0.28982(32) 1.06214(49) 0.5 3.25(20) H10 H 1 0.61234(77) -0.21702(33) 0.93300(72) 1 3.25(20) N1 N 1 0.5246(19) -0.2429(14) 1.0614(13) 1 3.25(20) C21 C 1 0.4380(27) -0.3029(10) 1.0708(13) 1 3.25(20) C22 C 1 0.3395(15) -0.31707(55) 1.1574(19) 1 3.25(20) N2 N 1 0.3261(20) -0.2715(14) 1.2360(12) 1 3.25(20) C23 C 1 0.4127(28) -0.21150(95) 1.2266(13) 1 3.25(20) C24 C 1 0.5112(17) -0.19733(57) 1.1399(20) 1 3.25(20) H13 H 1 0.4450(45) -0.3357(16) 1.0171(20) 1 3.25(20) H14 H 1 0.2805(25) -0.35938(82) 1.1618(32) 1 3.25(20) H15 H 1 0.4057(46) -0.1787(16) 1.2802(20) 1 3.25(20) H16 H 1 0.5702(27) -0.15502(85) 1.1355(32) 1 3.25(20) #============================================================================== # 10. MOLECULAR GEOMETRY _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 O1 1.524(6) C1 C8 1.524(8) C1 C9 1.501(4) C1 C20 1.502(5) O1 C2 1.359(8) C2 C3 1.48(1) C2 O2 1.213(7) C3 C4 1.38(1) C3 C8 1.388(4) C4 C5 1.38(1) C4 H1 0.930(6) C5 C6 1.40(1) C5 H2 0.93(1) C6 C7 1.375(9) C6 H3 0.930(9) C7 C8 1.383(7) C7 H4 0.930(7) C9 C10 1.399(5) C9 C14 1.392(5) C10 C11 1.379(5) C10 H5 0.930(6) C11 C12 1.401(7) C11 H6 0.930(6) C12 C13 1.392(8) C12 O3 1.360(8) C13 C14 1.387(7) C13 H8 0.930(8) C14 O4 1.385(7) O4 C15 1.385(7) C15 C16 1.387(7) C15 C20 1.392(6) C16 C17 1.392(8) C16 H9 0.930(9) C17 C18 1.401(9) C17 O5 1.360(8) C18 C19 1.379(6) C18 H11 0.930(7) C19 C20 1.399(5) C19 H12 0.930(7) O3 H7a 0.85(1) O3 H7b 0.850(9) O5 H10 0.85(1) N1 C21 1.33(3) N1 C24 1.33(3) C21 C22 1.39(3) C21 H13 0.93(3) C22 N2 1.33(3) C22 H14 0.93(2) N2 C23 1.33(3) C23 C24 1.39(3) C23 H15 0.93(3) C24 H16 0.93(2) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O1 C1 C8 101.2(3) O1 C1 C9 106.9(3) O1 C1 C20 107.0(3) C8 C1 C9 114.5(3) C8 C1 C20 114.5(3) C9 C1 C20 111.7(3) C1 O1 C2 111.2(4) O1 C2 C3 109.0(4) O1 C2 O2 122.0(5) C3 C2 O2 128.9(5) C2 C3 C4 129.3(5) C2 C3 C8 108.1(4) C4 C3 C8 122.6(5) C3 C4 C5 117.5(6) C3 C4 H1 122.5(7) C5 C4 H1 120.0(8) C4 C5 C6 120.1(6) C4 C5 H2 119.9(8) C6 C5 H2 120.0(8) C5 C6 C7 122.1(5) C5 C6 H3 117.9(7) C7 C6 H3 120.0(7) C6 C7 C8 117.7(4) C6 C7 H4 122.3(5) C8 C7 H4 120.0(5) C1 C8 C3 110.4(3) C1 C8 C7 129.5(4) C3 C8 C7 120.0(4) C1 C9 C10 121.4(3) C1 C9 C14 121.5(3) C10 C9 C14 116.9(3) C9 C10 C11 122.4(4) C9 C10 H5 117.6(4) C11 C10 H5 120.0(5) C10 C11 C12 119.2(4) C10 C11 H6 120.7(6) C12 C11 H6 120.0(6) C11 C12 C13 119.8(5) C11 C12 O3 122.2(5) C13 C12 O3 118.0(5) C12 C13 C14 119.3(5) C12 C13 H8 120.6(6) C14 C13 H8 120.0(6) C9 C14 C13 122.3(4) C9 C14 O4 122.5(4) C13 C14 O4 115.2(4) C14 O4 C15 118.9(4) O4 C15 C16 115.2(4) O4 C15 C20 122.5(4) C16 C15 C20 122.3(4) C15 C16 C17 119.3(5) C15 C16 H9 120.6(6) C17 C16 H9 120.0(6) C16 C17 C18 119.8(5) C16 C17 O5 118.0(5) C18 C17 O5 122.1(5) C17 C18 C19 119.2(5) C17 C18 H11 120.8(6) C19 C18 H11 120.0(6) C18 C19 C20 122.4(4) C18 C19 H12 117.3(5) C20 C19 H12 120.0(5) C1 C20 C15 121.5(3) C1 C20 C19 121.4(3) C15 C20 C19 116.9(4) C12 O3 H7a 109.5(8) C12 O3 H7b 109.5(8) H7a O3 H7b 133(1) C17 O5 H10 115.0(8) C21 N1 C24 116(2) N1 C21 C22 122(2) N1 C21 H13 118(3) C22 C21 H13 120(3) C21 C22 N2 122(2) C21 C22 H14 120(2) N2 C22 H14 118(2) C22 N2 C23 116(2) N2 C23 C24 122(2) N2 C23 H15 118(3) C24 C23 H15 120(3) N1 C24 C23 122(2) N1 C24 H16 118(2) C23 C24 H16 120(2) _database_code_depnum_ccdc_archive 'CCDC 908180' ####################################################################### # # 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_4a #TrackingRef '4.cif' _audit_creation_date 2012-10-26T20:15:15-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C46 H30 N2 O5' _chemical_formula_moiety 'C20 H12 O5, 2(C13 H9 N)' _chemical_formula_weight 690.72 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _cell_length_a 8.6428(3) _cell_length_b 19.6270(7) _cell_length_c 20.9268(9) _cell_angle_alpha 90 _cell_angle_beta 98.748(4) _cell_angle_gamma 90 _cell_volume 3508.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.35 _cell_measurement_reflns_used 4217 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour 'pale orange' _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.686 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_absorpt_correction_T_min 0.6860 _exptl_absorpt_correction_T_max 0.8965 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_unetI/netI 0.0344 _diffrn_reflns_number 11932 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.1 _diffrn_reflns_theta_max 72.02 _diffrn_reflns_theta_full 72.02 _diffrn_measured_fraction_theta_full 0.966 _diffrn_measured_fraction_theta_max 0.966 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_detector_area_resol_mean 9 _reflns_number_total 6669 _reflns_number_gt 5207 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury (Macrae, 2008)' _computing_publication_material 'WinGX (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.3815P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 6669 _refine_ls_number_parameters 480 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0573 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1176 _refine_ls_wR_factor_gt 0.1066 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.21 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.039 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.53271(17) 0.98569(6) 0.57433(6) 0.0470(3) Uani 1 1 d . . . O1 O 0.43151(13) 0.88855(5) 0.52933(5) 0.0324(2) Uani 1 1 d . . . O5 O 0.15229(16) 0.77754(6) 0.25114(6) 0.0433(3) Uani 1 1 d . . . H5O H 0.1023 0.7407 0.2498 0.065 Uiso 1 1 calc R . . O4 O 0.26813(13) 0.71207(6) 0.47026(5) 0.0360(3) Uani 1 1 d . . . O3 O 0.39540(12) 0.61197(5) 0.67597(5) 0.0292(2) Uani 1 1 d . . . H3O H 0.3237 0.5858 0.6591 0.044 Uiso 1 1 calc R . . N1 N 0.17199(14) 0.52490(6) 0.61903(6) 0.0272(3) Uani 1 1 d . . . C1 C 0.5515(2) 0.93325(8) 0.54621(7) 0.0348(4) Uani 1 1 d . . . C2 C 0.6937(2) 0.90514(8) 0.52585(7) 0.0348(4) Uani 1 1 d . . . C3 C 0.8429(2) 0.93295(10) 0.53024(9) 0.0467(5) Uani 1 1 d . . . H3 H 0.8652 0.9771 0.5478 0.056 Uiso 1 1 calc R . . C4 C 0.9579(2) 0.89423(12) 0.50820(10) 0.0518(5) Uani 1 1 d . . . H4 H 1.0614 0.9116 0.5113 0.062 Uiso 1 1 calc R . . C5 C 0.9228(2) 0.83011(11) 0.48152(10) 0.0482(5) Uani 1 1 d . . . H5 H 1.0029 0.8044 0.4663 0.058 Uiso 1 1 calc R . . C6 C 0.77301(19) 0.80278(9) 0.47662(8) 0.0366(4) Uani 1 1 d . . . H6 H 0.7494 0.7591 0.4581 0.044 Uiso 1 1 calc R . . C7 C 0.65932(18) 0.84147(8) 0.49974(7) 0.0301(3) Uani 1 1 d . . . C8 C 0.48880(17) 0.82468(7) 0.50181(7) 0.0270(3) Uani 1 1 d . . . C20 C 0.39710(17) 0.81247(7) 0.43571(7) 0.0258(3) Uani 1 1 d . . . C19 C 0.41214(18) 0.85502(8) 0.38333(8) 0.0300(3) Uani 1 1 d . . . H19 H 0.4805 0.8931 0.39 0.036 Uiso 1 1 calc R . . C18 C 0.33082(19) 0.84331(8) 0.32245(8) 0.0324(3) Uani 1 1 d . . . H18 H 0.3436 0.873 0.2878 0.039 Uiso 1 1 calc R . . C17 C 0.22938(19) 0.78757(8) 0.31172(8) 0.0323(3) Uani 1 1 d . . . C16 C 0.21084(18) 0.74465(8) 0.36257(7) 0.0323(3) Uani 1 1 d . . . H16 H 0.1417 0.7068 0.356 0.039 Uiso 1 1 calc R . . C15 C 0.29508(17) 0.75784(8) 0.42343(7) 0.0283(3) Uani 1 1 d . . . C14 C 0.35734(17) 0.71658(8) 0.53062(7) 0.0267(3) Uani 1 1 d . . . C13 C 0.33065(17) 0.66460(8) 0.57232(7) 0.0274(3) Uani 1 1 d . . . H13 H 0.2551 0.6304 0.5586 0.033 Uiso 1 1 calc R . . C12 C 0.41448(17) 0.66270(7) 0.63414(7) 0.0264(3) Uani 1 1 d . . . C11 C 0.52359(18) 0.71391(8) 0.65357(7) 0.0309(3) Uani 1 1 d . . . H11 H 0.5811 0.7135 0.696 0.037 Uiso 1 1 calc R . . C10 C 0.54776(18) 0.76518(8) 0.61092(7) 0.0307(3) Uani 1 1 d . . . H10 H 0.6224 0.7997 0.6248 0.037 Uiso 1 1 calc R . . C9 C 0.46546(17) 0.76778(7) 0.54777(7) 0.0260(3) Uani 1 1 d . . . C33 C 0.20077(17) 0.47486(7) 0.57825(7) 0.0270(3) Uani 1 1 d . . . C32 C 0.35154(19) 0.47081(9) 0.55938(8) 0.0340(3) Uani 1 1 d . . . H32 H 0.4311 0.5018 0.577 0.041 Uiso 1 1 calc R . . C31 C 0.3827(2) 0.42280(9) 0.51627(8) 0.0402(4) Uani 1 1 d . . . H31 H 0.4839 0.4209 0.5039 0.048 Uiso 1 1 calc R . . C30 C 0.2670(2) 0.37554(9) 0.48954(8) 0.0421(4) Uani 1 1 d . . . H30 H 0.2903 0.3429 0.4589 0.05 Uiso 1 1 calc R . . C29 C 0.1226(2) 0.37674(8) 0.50767(8) 0.0388(4) Uani 1 1 d . . . H29 H 0.0461 0.3444 0.4899 0.047 Uiso 1 1 calc R . . C28 C 0.08419(18) 0.42598(8) 0.55308(7) 0.0301(3) Uani 1 1 d . . . C27 C -0.06003(18) 0.42951(8) 0.57441(8) 0.0329(3) Uani 1 1 d . . . H27 H -0.1382 0.3966 0.5599 0.04 Uiso 1 1 calc R . . C26 C -0.09142(18) 0.48035(8) 0.61658(8) 0.0315(3) Uani 1 1 d . . . C25 C -0.23695(19) 0.48712(10) 0.64006(9) 0.0411(4) Uani 1 1 d . . . H25 H -0.3167 0.4541 0.6285 0.049 Uiso 1 1 calc R . . C24 C -0.2631(2) 0.53992(11) 0.67864(9) 0.0454(4) Uani 1 1 d . . . H24 H -0.3606 0.5436 0.6941 0.055 Uiso 1 1 calc R . . C23 C -0.1460(2) 0.58960(10) 0.69604(9) 0.0425(4) Uani 1 1 d . . . H23 H -0.1673 0.6272 0.722 0.051 Uiso 1 1 calc R . . C22 C -0.00344(19) 0.58480(8) 0.67646(8) 0.0342(3) Uani 1 1 d . . . H22 H 0.0743 0.6184 0.6893 0.041 Uiso 1 1 calc R . . C21 C 0.02912(17) 0.52940(8) 0.63676(7) 0.0274(3) Uani 1 1 d . . . N2 N 0.98411(16) 0.65890(7) 0.24070(6) 0.0348(3) Uani 1 1 d . . . C34 C 0.84395(19) 0.65247(9) 0.26111(8) 0.0343(4) Uani 1 1 d . . . C35 C 0.7857(2) 0.70723(10) 0.29548(8) 0.0454(4) Uani 1 1 d . . . H35 H 0.8468 0.7473 0.3046 0.054 Uiso 1 1 calc R . . C36 C 0.6428(3) 0.70249(13) 0.31534(9) 0.0571(6) Uani 1 1 d . . . H36 H 0.6055 0.7393 0.3383 0.068 Uiso 1 1 calc R . . C37 C 0.5498(3) 0.64358(14) 0.30214(12) 0.0627(6) Uani 1 1 d . . . H37 H 0.4495 0.6415 0.3154 0.075 Uiso 1 1 calc R . . C38 C 0.6017(2) 0.59044(12) 0.27102(11) 0.0553(5) Uani 1 1 d . . . H38 H 0.5385 0.5508 0.2633 0.066 Uiso 1 1 calc R . . C39 C 0.74985(19) 0.59260(9) 0.24945(8) 0.0382(4) Uani 1 1 d . . . C40 C 0.8095(2) 0.53902(9) 0.21734(9) 0.0418(4) Uani 1 1 d . . . H40 H 0.7497 0.4985 0.2089 0.05 Uiso 1 1 calc R . . C41 C 0.9548(2) 0.54372(9) 0.19745(8) 0.0393(4) Uani 1 1 d . . . C42 C 1.0231(3) 0.48978(11) 0.16549(9) 0.0548(5) Uani 1 1 d . . . H42 H 0.9693 0.4477 0.1577 0.066 Uiso 1 1 calc R . . C43 C 1.1641(3) 0.49838(15) 0.14621(10) 0.0687(7) Uani 1 1 d . . . H43 H 1.2086 0.4621 0.1251 0.082 Uiso 1 1 calc R . . C44 C 1.2461(3) 0.56058(16) 0.15704(10) 0.0667(7) Uani 1 1 d . . . H44 H 1.3446 0.5657 0.1427 0.08 Uiso 1 1 calc R . . C45 C 1.1865(2) 0.61319(13) 0.18765(9) 0.0533(5) Uani 1 1 d . . . H45 H 1.2432 0.6547 0.1945 0.064 Uiso 1 1 calc R . . C46 C 1.03920(19) 0.60625(9) 0.20944(8) 0.0369(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 O2 0.0836(10) 0.0231(6) 0.0353(6) -0.0062(5) 0.0120(6) -0.0099(6) O1 0.0431(6) 0.0200(5) 0.0350(6) -0.0045(4) 0.0089(5) -0.0014(4) O5 0.0586(8) 0.0356(6) 0.0310(6) 0.0077(5) -0.0085(5) -0.0143(6) O4 0.0411(6) 0.0356(6) 0.0283(5) 0.0074(5) -0.0040(4) -0.0181(5) O3 0.0334(6) 0.0286(5) 0.0256(5) 0.0006(4) 0.0042(4) -0.0054(4) N1 0.0288(6) 0.0245(6) 0.0279(6) 0.0009(5) 0.0034(5) -0.0024(5) C1 0.0563(10) 0.0218(8) 0.0257(7) -0.0007(6) 0.0038(7) -0.0102(7) C2 0.0454(9) 0.0305(8) 0.0267(7) 0.0022(6) -0.0001(6) -0.0121(7) C3 0.0571(12) 0.0440(10) 0.0358(9) 0.0058(8) -0.0030(8) -0.0264(9) C4 0.0370(9) 0.0666(14) 0.0493(11) 0.0147(10) -0.0013(8) -0.0209(9) C5 0.0344(9) 0.0579(12) 0.0531(11) 0.0150(10) 0.0093(8) -0.0014(8) C6 0.0334(8) 0.0355(9) 0.0407(9) 0.0044(7) 0.0051(7) -0.0009(7) C7 0.0327(8) 0.0274(8) 0.0293(7) 0.0032(6) 0.0020(6) -0.0060(6) C8 0.0310(7) 0.0190(7) 0.0313(7) -0.0023(6) 0.0060(6) -0.0007(6) C20 0.0290(7) 0.0200(7) 0.0289(7) -0.0011(6) 0.0056(6) -0.0002(6) C19 0.0352(8) 0.0202(7) 0.0348(8) -0.0001(6) 0.0060(6) -0.0031(6) C18 0.0425(9) 0.0241(7) 0.0307(8) 0.0049(6) 0.0056(6) -0.0015(6) C17 0.0380(8) 0.0278(8) 0.0292(8) 0.0035(6) -0.0012(6) -0.0009(6) C16 0.0360(8) 0.0283(8) 0.0307(8) 0.0032(6) -0.0012(6) -0.0086(6) C15 0.0310(8) 0.0253(7) 0.0284(7) 0.0056(6) 0.0035(6) -0.0026(6) C14 0.0271(7) 0.0273(7) 0.0250(7) -0.0006(6) 0.0017(5) -0.0020(6) C13 0.0273(7) 0.0260(7) 0.0286(7) -0.0023(6) 0.0039(6) -0.0059(6) C12 0.0303(7) 0.0241(7) 0.0259(7) -0.0014(6) 0.0077(6) 0.0004(6) C11 0.0359(8) 0.0295(8) 0.0259(7) -0.0024(6) 0.0003(6) -0.0048(6) C10 0.0348(8) 0.0255(8) 0.0306(8) -0.0047(6) 0.0017(6) -0.0069(6) C9 0.0286(7) 0.0222(7) 0.0276(7) -0.0020(6) 0.0053(6) -0.0015(6) C33 0.0309(7) 0.0231(7) 0.0265(7) 0.0034(6) 0.0029(6) 0.0007(6) C32 0.0326(8) 0.0345(9) 0.0352(8) 0.0018(7) 0.0065(6) -0.0007(7) C31 0.0426(9) 0.0423(10) 0.0382(9) 0.0030(8) 0.0142(7) 0.0072(8) C30 0.0602(11) 0.0326(9) 0.0338(9) -0.0033(7) 0.0081(8) 0.0101(8) C29 0.0523(10) 0.0257(8) 0.0361(9) -0.0024(7) -0.0009(7) 0.0015(7) C28 0.0360(8) 0.0220(7) 0.0304(7) 0.0033(6) -0.0016(6) -0.0001(6) C27 0.0312(8) 0.0269(8) 0.0380(8) 0.0037(6) -0.0035(6) -0.0072(6) C26 0.0278(7) 0.0316(8) 0.0338(8) 0.0077(7) 0.0009(6) -0.0014(6) C25 0.0276(8) 0.0487(10) 0.0464(10) 0.0097(8) 0.0036(7) -0.0032(7) C24 0.0308(9) 0.0606(12) 0.0467(10) 0.0092(9) 0.0113(7) 0.0109(8) C23 0.0440(10) 0.0470(11) 0.0375(9) 0.0023(8) 0.0088(7) 0.0156(8) C22 0.0373(9) 0.0309(8) 0.0341(8) 0.0009(7) 0.0041(6) 0.0040(7) C21 0.0295(7) 0.0253(7) 0.0273(7) 0.0041(6) 0.0035(6) -0.0002(6) N2 0.0356(7) 0.0363(8) 0.0309(7) 0.0031(6) -0.0005(5) -0.0046(6) C34 0.0358(8) 0.0378(9) 0.0271(7) 0.0062(7) -0.0018(6) 0.0031(7) C35 0.0539(11) 0.0464(11) 0.0325(9) 0.0005(8) -0.0037(7) 0.0126(9) C36 0.0625(13) 0.0714(15) 0.0374(10) 0.0106(10) 0.0079(9) 0.0345(12) C37 0.0457(11) 0.0812(17) 0.0641(14) 0.0284(13) 0.0176(10) 0.0192(12) C38 0.0364(10) 0.0643(14) 0.0646(13) 0.0263(11) 0.0058(9) -0.0008(9) C39 0.0336(8) 0.0409(9) 0.0377(9) 0.0130(7) -0.0016(7) -0.0018(7) C40 0.0444(10) 0.0342(9) 0.0424(9) 0.0072(8) -0.0071(7) -0.0067(8) C41 0.0484(10) 0.0386(9) 0.0279(8) 0.0022(7) -0.0040(7) 0.0032(8) C42 0.0757(14) 0.0482(12) 0.0362(10) -0.0025(8) -0.0056(9) 0.0193(10) C43 0.0840(17) 0.0866(18) 0.0333(10) -0.0022(11) 0.0021(10) 0.0433(15) C44 0.0551(13) 0.108(2) 0.0396(11) 0.0134(12) 0.0169(9) 0.0261(14) C45 0.0430(10) 0.0766(15) 0.0411(10) 0.0121(10) 0.0090(8) 0.0005(10) C46 0.0363(8) 0.0465(10) 0.0267(7) 0.0043(7) 0.0005(6) 0.0009(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C1 1.209(2) . ? O1 C1 1.3631(19) . ? O1 C8 1.4950(17) . ? O5 C17 1.3539(19) . ? O5 H5O 0.84 . ? O4 C15 1.3751(18) . ? O4 C14 1.3790(17) . ? O3 C12 1.3523(18) . ? O3 H3O 0.84 . ? N1 C21 1.3452(19) . ? N1 C33 1.3487(19) . ? C1 C2 1.468(3) . ? C2 C7 1.378(2) . ? C2 C3 1.390(2) . ? C3 C4 1.385(3) . ? C3 H3 0.95 . ? C4 C5 1.391(3) . ? C4 H4 0.95 . ? C5 C6 1.390(2) . ? C5 H5 0.95 . ? C6 C7 1.386(2) . ? C6 H6 0.95 . ? C7 C8 1.517(2) . ? C8 C20 1.505(2) . ? C8 C9 1.507(2) . ? C20 C15 1.387(2) . ? C20 C19 1.400(2) . ? C19 C18 1.378(2) . ? C19 H19 0.95 . ? C18 C17 1.399(2) . ? C18 H18 0.95 . ? C17 C16 1.386(2) . ? C16 C15 1.392(2) . ? C16 H16 0.95 . ? C14 C9 1.382(2) . ? C14 C13 1.384(2) . ? C13 C12 1.384(2) . ? C13 H13 0.95 . ? C12 C11 1.396(2) . ? C11 C10 1.382(2) . ? C11 H11 0.95 . ? C10 C9 1.403(2) . ? C10 H10 0.95 . ? C33 C32 1.420(2) . ? C33 C28 1.433(2) . ? C32 C31 1.359(2) . ? C32 H32 0.95 . ? C31 C30 1.415(3) . ? C31 H31 0.95 . ? C30 C29 1.358(3) . ? C30 H30 0.95 . ? C29 C28 1.429(2) . ? C29 H29 0.95 . ? C28 C27 1.388(2) . ? C27 C26 1.386(2) . ? C27 H27 0.95 . ? C26 C25 1.424(2) . ? C26 C21 1.434(2) . ? C25 C24 1.354(3) . ? C25 H25 0.95 . ? C24 C23 1.413(3) . ? C24 H24 0.95 . ? C23 C22 1.360(2) . ? C23 H23 0.95 . ? C22 C21 1.422(2) . ? C22 H22 0.95 . ? N2 C46 1.348(2) . ? N2 C34 1.350(2) . ? C34 C35 1.427(2) . ? C34 C39 1.429(2) . ? C35 C36 1.365(3) . ? C35 H35 0.95 . ? C36 C37 1.412(3) . ? C36 H36 0.95 . ? C37 C38 1.342(3) . ? C37 H37 0.95 . ? C38 C39 1.422(3) . ? C38 H38 0.95 . ? C39 C40 1.389(3) . ? C40 C41 1.384(3) . ? C40 H40 0.95 . ? C41 C42 1.427(3) . ? C41 C46 1.430(2) . ? C42 C43 1.351(3) . ? C42 H42 0.95 . ? C43 C44 1.413(4) . ? C43 H43 0.95 . ? C44 C45 1.357(3) . ? C44 H44 0.95 . ? C45 C46 1.423(3) . ? C45 H45 0.95 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C8 110.86(12) . . ? C17 O5 H5O 109.5 . . ? C15 O4 C14 118.63(11) . . ? C12 O3 H3O 109.5 . . ? C21 N1 C33 119.19(13) . . ? O2 C1 O1 121.41(17) . . ? O2 C1 C2 129.90(16) . . ? O1 C1 C2 108.67(13) . . ? C7 C2 C3 121.60(17) . . ? C7 C2 C1 108.44(14) . . ? C3 C2 C1 129.95(16) . . ? C4 C3 C2 117.90(18) . . ? C4 C3 H3 121.1 . . ? C2 C3 H3 121.1 . . ? C3 C4 C5 120.42(17) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 121.48(19) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C7 C6 C5 117.67(17) . . ? C7 C6 H6 121.2 . . ? C5 C6 H6 121.2 . . ? C2 C7 C6 120.92(15) . . ? C2 C7 C8 109.72(14) . . ? C6 C7 C8 129.36(14) . . ? O1 C8 C20 109.18(12) . . ? O1 C8 C9 106.93(11) . . ? C20 C8 C9 111.45(12) . . ? O1 C8 C7 102.05(11) . . ? C20 C8 C7 112.73(12) . . ? C9 C8 C7 113.83(12) . . ? C15 C20 C19 116.63(14) . . ? C15 C20 C8 121.61(13) . . ? C19 C20 C8 121.74(13) . . ? C18 C19 C20 121.99(14) . . ? C18 C19 H19 119 . . ? C20 C19 H19 119 . . ? C19 C18 C17 119.87(14) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? O5 C17 C16 122.19(14) . . ? O5 C17 C18 118.12(14) . . ? C16 C17 C18 119.69(14) . . ? C17 C16 C15 118.96(14) . . ? C17 C16 H16 120.5 . . ? C15 C16 H16 120.5 . . ? O4 C15 C20 123.01(13) . . ? O4 C15 C16 114.13(13) . . ? C20 C15 C16 122.86(14) . . ? O4 C14 C9 123.12(13) . . ? O4 C14 C13 113.98(13) . . ? C9 C14 C13 122.90(14) . . ? C12 C13 C14 119.69(13) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? O3 C12 C13 121.80(13) . . ? O3 C12 C11 119.03(13) . . ? C13 C12 C11 119.16(14) . . ? C10 C11 C12 119.87(14) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C11 C10 C9 122.01(14) . . ? C11 C10 H10 119 . . ? C9 C10 H10 119 . . ? C14 C9 C10 116.36(14) . . ? C14 C9 C8 121.59(13) . . ? C10 C9 C8 122.01(13) . . ? N1 C33 C32 118.82(14) . . ? N1 C33 C28 122.23(14) . . ? C32 C33 C28 118.95(14) . . ? C31 C32 C33 120.40(16) . . ? C31 C32 H32 119.8 . . ? C33 C32 H32 119.8 . . ? C32 C31 C30 121.15(16) . . ? C32 C31 H31 119.4 . . ? C30 C31 H31 119.4 . . ? C29 C30 C31 120.14(16) . . ? C29 C30 H30 119.9 . . ? C31 C30 H30 119.9 . . ? C30 C29 C28 120.89(16) . . ? C30 C29 H29 119.6 . . ? C28 C29 H29 119.6 . . ? C27 C28 C29 123.94(15) . . ? C27 C28 C33 117.64(14) . . ? C29 C28 C33 118.41(15) . . ? C26 C27 C28 120.87(14) . . ? C26 C27 H27 119.6 . . ? C28 C27 H27 119.6 . . ? C27 C26 C25 123.74(15) . . ? C27 C26 C21 117.84(14) . . ? C25 C26 C21 118.42(15) . . ? C24 C25 C26 120.90(17) . . ? C24 C25 H25 119.5 . . ? C26 C25 H25 119.5 . . ? C25 C24 C23 120.26(16) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C22 C23 C24 121.40(17) . . ? C22 C23 H23 119.3 . . ? C24 C23 H23 119.3 . . ? C23 C22 C21 119.87(16) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? N1 C21 C22 118.87(14) . . ? N1 C21 C26 122.07(14) . . ? C22 C21 C26 119.06(14) . . ? C46 N2 C34 118.81(15) . . ? N2 C34 C35 119.43(16) . . ? N2 C34 C39 122.53(16) . . ? C35 C34 C39 118.04(16) . . ? C36 C35 C34 120.5(2) . . ? C36 C35 H35 119.8 . . ? C34 C35 H35 119.8 . . ? C35 C36 C37 120.7(2) . . ? C35 C36 H36 119.6 . . ? C37 C36 H36 119.6 . . ? C38 C37 C36 120.59(19) . . ? C38 C37 H37 119.7 . . ? C36 C37 H37 119.7 . . ? C37 C38 C39 121.0(2) . . ? C37 C38 H38 119.5 . . ? C39 C38 H38 119.5 . . ? C40 C39 C38 123.35(18) . . ? C40 C39 C34 117.49(16) . . ? C38 C39 C34 119.15(18) . . ? C41 C40 C39 121.03(16) . . ? C41 C40 H40 119.5 . . ? C39 C40 H40 119.5 . . ? C40 C41 C42 123.40(19) . . ? C40 C41 C46 117.79(16) . . ? C42 C41 C46 118.81(18) . . ? C43 C42 C41 120.2(2) . . ? C43 C42 H42 119.9 . . ? C41 C42 H42 119.9 . . ? C42 C43 C44 120.9(2) . . ? C42 C43 H43 119.6 . . ? C44 C43 H43 119.6 . . ? C45 C44 C43 121.1(2) . . ? C45 C44 H44 119.5 . . ? C43 C44 H44 119.5 . . ? C44 C45 C46 120.0(2) . . ? C44 C45 H45 120 . . ? C46 C45 H45 120 . . ? N2 C46 C45 118.78(18) . . ? N2 C46 C41 122.30(15) . . ? C45 C46 C41 118.91(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 O1 C1 O2 -173.77(14) . . . . ? C8 O1 C1 C2 5.06(16) . . . . ? O2 C1 C2 C7 175.50(17) . . . . ? O1 C1 C2 C7 -3.20(18) . . . . ? O2 C1 C2 C3 -4.0(3) . . . . ? O1 C1 C2 C3 177.31(16) . . . . ? C7 C2 C3 C4 -0.8(3) . . . . ? C1 C2 C3 C4 178.62(17) . . . . ? C2 C3 C4 C5 1.2(3) . . . . ? C3 C4 C5 C6 -0.5(3) . . . . ? C4 C5 C6 C7 -0.5(3) . . . . ? C3 C2 C7 C6 -0.2(2) . . . . ? C1 C2 C7 C6 -179.74(14) . . . . ? C3 C2 C7 C8 179.62(15) . . . . ? C1 C2 C7 C8 0.08(17) . . . . ? C5 C6 C7 C2 0.8(2) . . . . ? C5 C6 C7 C8 -178.94(16) . . . . ? C1 O1 C8 C20 -124.28(13) . . . . ? C1 O1 C8 C9 115.02(13) . . . . ? C1 O1 C8 C7 -4.77(15) . . . . ? C2 C7 C8 O1 2.70(16) . . . . ? C6 C7 C8 O1 -177.50(15) . . . . ? C2 C7 C8 C20 119.68(14) . . . . ? C6 C7 C8 C20 -60.5(2) . . . . ? C2 C7 C8 C9 -112.12(15) . . . . ? C6 C7 C8 C9 67.7(2) . . . . ? O1 C8 C20 C15 -112.58(15) . . . . ? C9 C8 C20 C15 5.3(2) . . . . ? C7 C8 C20 C15 134.75(15) . . . . ? O1 C8 C20 C19 68.39(17) . . . . ? C9 C8 C20 C19 -173.71(13) . . . . ? C7 C8 C20 C19 -44.28(19) . . . . ? C15 C20 C19 C18 -0.4(2) . . . . ? C8 C20 C19 C18 178.70(14) . . . . ? C20 C19 C18 C17 0.1(2) . . . . ? C19 C18 C17 O5 -179.61(15) . . . . ? C19 C18 C17 C16 0.3(2) . . . . ? O5 C17 C16 C15 179.44(15) . . . . ? C18 C17 C16 C15 -0.5(2) . . . . ? C14 O4 C15 C20 -6.5(2) . . . . ? C14 O4 C15 C16 173.60(14) . . . . ? C19 C20 C15 O4 -179.70(14) . . . . ? C8 C20 C15 O4 1.2(2) . . . . ? C19 C20 C15 C16 0.2(2) . . . . ? C8 C20 C15 C16 -178.87(14) . . . . ? C17 C16 C15 O4 -179.87(15) . . . . ? C17 C16 C15 C20 0.2(2) . . . . ? C15 O4 C14 C9 4.5(2) . . . . ? C15 O4 C14 C13 -174.53(13) . . . . ? O4 C14 C13 C12 179.07(13) . . . . ? C9 C14 C13 C12 0.0(2) . . . . ? C14 C13 C12 O3 -178.23(13) . . . . ? C14 C13 C12 C11 0.7(2) . . . . ? O3 C12 C11 C10 178.27(14) . . . . ? C13 C12 C11 C10 -0.7(2) . . . . ? C12 C11 C10 C9 0.0(2) . . . . ? O4 C14 C9 C10 -179.67(14) . . . . ? C13 C14 C9 C10 -0.7(2) . . . . ? O4 C14 C9 C8 2.6(2) . . . . ? C13 C14 C9 C8 -178.40(14) . . . . ? C11 C10 C9 C14 0.7(2) . . . . ? C11 C10 C9 C8 178.39(14) . . . . ? O1 C8 C9 C14 112.11(15) . . . . ? C20 C8 C9 C14 -7.14(19) . . . . ? C7 C8 C9 C14 -135.99(15) . . . . ? O1 C8 C9 C10 -65.49(17) . . . . ? C20 C8 C9 C10 175.26(13) . . . . ? C7 C8 C9 C10 46.42(19) . . . . ? C21 N1 C33 C32 179.51(13) . . . . ? C21 N1 C33 C28 -0.1(2) . . . . ? N1 C33 C32 C31 -177.25(15) . . . . ? C28 C33 C32 C31 2.4(2) . . . . ? C33 C32 C31 C30 -0.5(3) . . . . ? C32 C31 C30 C29 -1.2(3) . . . . ? C31 C30 C29 C28 0.9(3) . . . . ? C30 C29 C28 C27 -179.05(16) . . . . ? C30 C29 C28 C33 1.0(2) . . . . ? N1 C33 C28 C27 -2.9(2) . . . . ? C32 C33 C28 C27 177.44(14) . . . . ? N1 C33 C28 C29 176.98(14) . . . . ? C32 C33 C28 C29 -2.6(2) . . . . ? C29 C28 C27 C26 -177.38(15) . . . . ? C33 C28 C27 C26 2.5(2) . . . . ? C28 C27 C26 C25 179.68(15) . . . . ? C28 C27 C26 C21 0.7(2) . . . . ? C27 C26 C25 C24 -176.67(16) . . . . ? C21 C26 C25 C24 2.3(2) . . . . ? C26 C25 C24 C23 0.3(3) . . . . ? C25 C24 C23 C22 -2.1(3) . . . . ? C24 C23 C22 C21 1.0(3) . . . . ? C33 N1 C21 C22 -176.05(13) . . . . ? C33 N1 C21 C26 3.6(2) . . . . ? C23 C22 C21 N1 -178.67(14) . . . . ? C23 C22 C21 C26 1.7(2) . . . . ? C27 C26 C21 N1 -3.9(2) . . . . ? C25 C26 C21 N1 177.05(14) . . . . ? C27 C26 C21 C22 175.75(14) . . . . ? C25 C26 C21 C22 -3.3(2) . . . . ? C46 N2 C34 C35 178.66(15) . . . . ? C46 N2 C34 C39 -1.6(2) . . . . ? N2 C34 C35 C36 178.55(15) . . . . ? C39 C34 C35 C36 -1.2(2) . . . . ? C34 C35 C36 C37 -0.2(3) . . . . ? C35 C36 C37 C38 1.5(3) . . . . ? C36 C37 C38 C39 -1.3(3) . . . . ? C37 C38 C39 C40 179.67(19) . . . . ? C37 C38 C39 C34 -0.2(3) . . . . ? N2 C34 C39 C40 1.8(2) . . . . ? C35 C34 C39 C40 -178.46(15) . . . . ? N2 C34 C39 C38 -178.35(15) . . . . ? C35 C34 C39 C38 1.4(2) . . . . ? C38 C39 C40 C41 -179.89(16) . . . . ? C34 C39 C40 C41 0.0(2) . . . . ? C39 C40 C41 C42 178.67(17) . . . . ? C39 C40 C41 C46 -1.7(2) . . . . ? C40 C41 C42 C43 178.63(17) . . . . ? C46 C41 C42 C43 -1.0(3) . . . . ? C41 C42 C43 C44 -0.2(3) . . . . ? C42 C43 C44 C45 0.7(3) . . . . ? C43 C44 C45 C46 0.0(3) . . . . ? C34 N2 C46 C45 179.68(15) . . . . ? C34 N2 C46 C41 -0.3(2) . . . . ? C44 C45 C46 N2 178.86(17) . . . . ? C44 C45 C46 C41 -1.1(3) . . . . ? C40 C41 C46 N2 2.0(2) . . . . ? C42 C41 C46 N2 -178.40(16) . . . . ? C40 C41 C46 C45 -178.02(16) . . . . ? C42 C41 C46 C45 1.6(2) . . . . ? _vrf_PLAT029_4 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.966 RESPONSE: The single crystals are very small in size and do not diffract sufficiently. ; _database_code_depnum_ccdc_archive 'CCDC 908181' ####################################################################### # # 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_6 #TrackingRef '6.cif' _audit_creation_date 2012-10-26T19:37:44-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C46 H30 N2 O5' _chemical_formula_moiety 'C20 H12 O5, 2(C13 H9 N)' _chemical_formula_weight 690.72 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, 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' '-x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'C m c 21' _symmetry_space_group_name_Hall 'C 2c -2' _cell_length_a 27.6912(12) _cell_length_b 15.3574(9) _cell_length_c 7.8814(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3351.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.35 _cell_measurement_reflns_used 4217 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour 'pale orange' _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_absorpt_correction_T_min 0.979 _exptl_absorpt_correction_T_max 0.991 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_unetI/netI 0.0533 _diffrn_reflns_number 4864 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.65 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_detector_area_resol_mean 9 _reflns_number_total 2671 _reflns_number_gt 2221 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury (Macrae, 2008)' _computing_publication_material 'WinGX (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0339P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2671 _refine_ls_number_parameters 257 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0521 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.0808 _refine_ls_wR_factor_gt 0.0756 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.972 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.161 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.037 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5 0.28535(13) 0.1012(3) 0.0214(5) Uani 1 2 d S . . O3 O 0.5 0.04932(13) 0.2438(3) 0.0227(6) Uani 1 2 d S . . O2 O 0.5 0.42775(14) 0.0333(3) 0.0276(6) Uani 1 2 d S . . O4 O 0.33058(6) 0.03415(10) 0.2592(2) 0.0283(4) Uani 1 1 d . . . H4O H 0.3063 0.0574 0.2205 0.042 Uiso 1 1 calc R . . N1 N 0.24579(7) 0.08618(13) 0.1143(3) 0.0270(5) Uani 1 1 d . . . C1 C 0.5 0.3522(2) -0.0120(4) 0.0199(8) Uani 1 2 d S . . C2 C 0.5 0.3163(2) -0.1859(4) 0.0200(8) Uani 1 2 d S . . C14 C 0.45691(8) 0.08230(14) 0.1817(3) 0.0191(5) Uani 1 1 d . . . C7 C 0.5 0.2262(2) -0.1744(4) 0.0191(7) Uani 1 2 d S . . C12 C 0.37053(8) 0.07286(15) 0.1926(3) 0.0218(5) Uani 1 1 d . . . C13 C 0.41555(8) 0.04330(15) 0.2455(3) 0.0215(5) Uani 1 1 d . . . H13 H 0.4179 -0.0022 0.323 0.026 Uiso 1 1 calc R . . C9 C 0.45515(8) 0.15050(14) 0.0656(3) 0.0199(5) Uani 1 1 d . . . C3 C 0.5 0.3596(2) -0.3395(4) 0.0219(8) Uani 1 2 d S . . H3 H 0.5 0.4201 -0.3445 0.026 Uiso 1 2 calc SR . . C26 C 0.17945(9) 0.01890(15) -0.0387(3) 0.0240(6) Uani 1 1 d . . . C4 C 0.5 0.3099(2) -0.4848(5) 0.0251(8) Uani 1 2 d S . . H4 H 0.5 0.3368 -0.5905 0.03 Uiso 1 2 calc SR . . C20 C 0.17663(9) 0.17486(15) 0.0198(3) 0.0241(6) Uani 1 1 d . . . C22 C 0.11114(9) 0.09885(17) -0.1475(3) 0.0284(6) Uani 1 1 d . . . H22 H 0.0952 0.1512 -0.1672 0.034 Uiso 1 1 calc R . . C6 C 0.5 0.1761(2) -0.3201(5) 0.0250(8) Uani 1 2 d S . . H6 H 0.5 0.1156 -0.3144 0.03 Uiso 1 2 calc SR . . C8 C 0.5 0.1975(2) 0.0106(4) 0.0194(8) Uani 1 2 d S . . C21 C 0.15553(9) 0.09895(16) -0.0596(3) 0.0238(6) Uani 1 1 d . . . C15 C 0.22074(9) 0.16564(16) 0.1078(3) 0.0259(6) Uani 1 1 d . . . C11 C 0.36745(8) 0.13978(15) 0.0724(3) 0.0266(6) Uani 1 1 d . . . H11 H 0.3375 0.1585 0.0331 0.032 Uiso 1 1 calc R . . C27 C 0.22535(8) 0.01868(16) 0.0435(3) 0.0270(6) Uani 1 1 d . . . H27 H 0.2421 -0.0338 0.047 0.032 Uiso 1 1 calc R . . C10 C 0.40933(8) 0.17765(16) 0.0129(3) 0.0261(6) Uani 1 1 d . . . H10 H 0.407 0.2229 -0.0651 0.031 Uiso 1 1 calc R . . C5 C 0.5 0.2186(2) -0.4737(5) 0.0289(9) Uani 1 2 d S . . H5 H 0.5 0.186 -0.5731 0.035 Uiso 1 2 calc SR . . C23 C 0.09125(9) 0.02244(17) -0.2040(3) 0.0331(7) Uani 1 1 d . . . H23 H 0.062 0.0235 -0.2619 0.04 Uiso 1 1 calc R . . C25 C 0.15817(9) -0.05981(17) -0.0962(3) 0.0285(6) Uani 1 1 d . . . H25 H 0.1739 -0.1127 -0.0799 0.034 Uiso 1 1 calc R . . C19 C 0.15391(10) 0.25783(16) 0.0224(3) 0.0318(6) Uani 1 1 d . . . H19 H 0.1252 0.2661 -0.0368 0.038 Uiso 1 1 calc R . . C16 C 0.24062(9) 0.23614(17) 0.1979(3) 0.0336(7) Uani 1 1 d . . . H16 H 0.2697 0.2295 0.2553 0.04 Uiso 1 1 calc R . . C17 C 0.21692(11) 0.31496(17) 0.2009(4) 0.0368(7) Uani 1 1 d . . . H17 H 0.2297 0.361 0.2629 0.044 Uiso 1 1 calc R . . C18 C 0.17380(10) 0.32615(17) 0.1114(4) 0.0373(7) Uani 1 1 d . . . H18 H 0.1585 0.38 0.1119 0.045 Uiso 1 1 calc R . . C24 C 0.11447(9) -0.05702(17) -0.1757(3) 0.0311(6) Uani 1 1 d . . . H24 H 0.1 -0.1085 -0.2115 0.037 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 0.0267(13) 0.0198(12) 0.0177(12) -0.0028(11) 0 0 O3 0.0166(12) 0.0207(12) 0.0308(14) 0.0059(10) 0 0 O2 0.0321(14) 0.0200(13) 0.0306(15) -0.0076(11) 0 0 O4 0.0171(9) 0.0325(10) 0.0352(11) 0.0077(8) 0.0004(8) -0.0029(8) N1 0.0199(11) 0.0323(12) 0.0290(12) 0.0038(10) -0.0008(10) 0.0015(9) C1 0.0141(17) 0.0189(19) 0.027(2) -0.0013(15) 0 0 C2 0.0159(18) 0.0221(19) 0.022(2) -0.0021(15) 0 0 C14 0.0179(12) 0.0175(12) 0.0218(13) -0.0018(11) -0.0025(11) 0.0008(10) C7 0.0141(17) 0.0200(18) 0.0231(19) -0.0017(15) 0 0 C12 0.0205(13) 0.0224(12) 0.0226(13) -0.0030(11) 0.0003(11) -0.0037(10) C13 0.0204(13) 0.0171(12) 0.0269(14) 0.0034(11) 0.0004(11) -0.0013(10) C9 0.0192(13) 0.0197(13) 0.0209(14) -0.0011(10) -0.0022(10) 0.0005(10) C3 0.0186(18) 0.0234(19) 0.024(2) 0.0020(15) 0 0 C26 0.0226(13) 0.0269(15) 0.0226(14) -0.0002(11) 0.0060(11) -0.0002(11) C4 0.0225(19) 0.032(2) 0.021(2) 0.0035(16) 0 0 C20 0.0243(13) 0.0246(13) 0.0232(13) 0.0003(11) 0.0022(12) -0.0009(11) C22 0.0216(15) 0.0346(15) 0.0291(15) 0.0024(12) 0.0023(12) -0.0007(12) C6 0.026(2) 0.0203(18) 0.028(2) -0.0032(17) 0 0 C8 0.0224(18) 0.0163(17) 0.0195(19) -0.0010(14) 0 0 C21 0.0214(13) 0.0258(14) 0.0242(14) 0.0030(11) 0.0032(12) 0.0016(11) C15 0.0264(14) 0.0286(13) 0.0228(13) 0.0031(12) 0.0051(12) -0.0066(11) C11 0.0192(13) 0.0309(14) 0.0296(16) 0.0036(12) -0.0042(11) 0.0028(11) C27 0.0250(14) 0.0270(15) 0.0290(15) 0.0039(12) 0.0019(12) 0.0020(11) C10 0.0268(14) 0.0249(13) 0.0266(15) 0.0053(12) -0.0017(12) 0.0014(11) C5 0.034(2) 0.029(2) 0.023(2) -0.0065(17) 0 0 C23 0.0251(14) 0.0454(19) 0.0287(16) 0.0002(13) -0.0048(12) -0.0073(13) C25 0.0305(15) 0.0255(15) 0.0295(15) -0.0046(11) 0.0077(13) -0.0020(12) C19 0.0320(15) 0.0299(14) 0.0336(16) 0.0010(13) 0.0026(13) 0.0017(12) C16 0.0346(16) 0.0388(16) 0.0275(15) 0.0021(13) -0.0010(13) -0.0149(13) C17 0.0547(19) 0.0285(15) 0.0272(16) -0.0027(13) 0.0053(14) -0.0129(14) C18 0.0535(19) 0.0240(14) 0.0343(16) 0.0025(13) 0.0074(16) -0.0007(13) C24 0.0272(15) 0.0354(16) 0.0309(15) -0.0037(12) 0.0013(13) -0.0093(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.360(4) . ? O1 C8 1.527(3) . ? O3 C14 1.385(2) 3_655 ? O3 C14 1.385(2) . ? O2 C1 1.214(4) . ? O4 C12 1.361(3) . ? O4 H4O 0.82 . ? N1 C27 1.306(3) . ? N1 C15 1.404(3) . ? C1 C2 1.477(4) . ? C2 C3 1.381(4) . ? C2 C7 1.387(4) . ? C14 C13 1.387(3) . ? C14 C9 1.392(3) . ? C7 C6 1.382(4) . ? C7 C8 1.523(5) . ? C12 C13 1.391(3) . ? C12 C11 1.400(3) . ? C13 H13 0.93 . ? C9 C10 1.399(3) . ? C9 C8 1.500(3) . ? C3 C4 1.377(5) . ? C3 H3 0.93 . ? C26 C21 1.406(3) . ? C26 C25 1.419(3) . ? C26 C27 1.427(3) . ? C4 C5 1.404(5) . ? C4 H4 0.93 . ? C20 C15 1.412(3) . ? C20 C19 1.421(3) . ? C20 C21 1.446(3) . ? C22 C23 1.371(4) . ? C22 C21 1.411(3) . ? C22 H22 0.93 . ? C6 C5 1.376(5) . ? C6 H6 0.93 . ? C8 C9 1.500(3) 3_655 ? C15 C16 1.407(3) . ? C11 C10 1.379(3) . ? C11 H11 0.93 . ? C27 H27 0.93 . ? C10 H10 0.93 . ? C5 H5 0.93 . ? C23 C24 1.397(3) . ? C23 H23 0.93 . ? C25 C24 1.364(4) . ? C25 H25 0.93 . ? C19 C18 1.377(3) . ? C19 H19 0.93 . ? C16 C17 1.377(4) . ? C16 H16 0.93 . ? C17 C18 1.397(4) . ? C17 H17 0.93 . ? C18 H18 0.93 . ? C24 H24 0.93 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C8 111.1(2) . . ? C14 O3 C14 118.9(2) 3_655 . ? C12 O4 H4O 109.5 . . ? C27 N1 C15 117.4(2) . . ? O2 C1 O1 121.9(3) . . ? O2 C1 C2 129.0(3) . . ? O1 C1 C2 109.1(3) . . ? C3 C2 C7 122.5(3) . . ? C3 C2 C1 129.3(3) . . ? C7 C2 C1 108.1(3) . . ? O3 C14 C13 115.2(2) . . ? O3 C14 C9 122.5(2) . . ? C13 C14 C9 122.3(2) . . ? C6 C7 C2 120.1(3) . . ? C6 C7 C8 129.4(3) . . ? C2 C7 C8 110.6(3) . . ? O4 C12 C13 118.0(2) . . ? O4 C12 C11 122.1(2) . . ? C13 C12 C11 119.8(2) . . ? C14 C13 C12 119.4(2) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C14 C9 C10 116.8(2) . . ? C14 C9 C8 121.5(2) . . ? C10 C9 C8 121.5(2) . . ? C4 C3 C2 117.6(3) . . ? C4 C3 H3 121.2 . . ? C2 C3 H3 121.2 . . ? C21 C26 C25 120.8(2) . . ? C21 C26 C27 118.4(2) . . ? C25 C26 C27 120.9(2) . . ? C3 C4 C5 120.1(4) . . ? C3 C4 H4 120 . . ? C5 C4 H4 120 . . ? C15 C20 C19 117.8(2) . . ? C15 C20 C21 118.8(2) . . ? C19 C20 C21 123.4(2) . . ? C23 C22 C21 120.7(2) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C5 C6 C7 117.8(3) . . ? C5 C6 H6 121.1 . . ? C7 C6 H6 121.1 . . ? C9 C8 C9 111.8(3) . 3_655 ? C9 C8 C7 114.56(16) . . ? C9 C8 C7 114.56(16) 3_655 . ? C9 C8 O1 106.85(16) . . ? C9 C8 O1 106.85(16) 3_655 . ? C7 C8 O1 101.1(2) . . ? C26 C21 C22 117.8(2) . . ? C26 C21 C20 117.6(2) . . ? C22 C21 C20 124.4(2) . . ? N1 C15 C16 117.2(2) . . ? N1 C15 C20 122.2(2) . . ? C16 C15 C20 120.6(2) . . ? C10 C11 C12 119.2(2) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? N1 C27 C26 125.3(2) . . ? N1 C27 H27 117.3 . . ? C26 C27 H27 117.3 . . ? C11 C10 C9 122.4(2) . . ? C11 C10 H10 118.8 . . ? C9 C10 H10 118.8 . . ? C6 C5 C4 121.9(3) . . ? C6 C5 H5 119 . . ? C4 C5 H5 119 . . ? C22 C23 C24 120.7(2) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C24 C25 C26 119.3(3) . . ? C24 C25 H25 120.4 . . ? C26 C25 H25 120.4 . . ? C18 C19 C20 120.9(3) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C17 C16 C15 119.9(3) . . ? C17 C16 H16 120 . . ? C15 C16 H16 120 . . ? C16 C17 C18 120.4(3) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C19 C18 C17 120.3(3) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C25 C24 C23 120.6(3) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? _database_code_depnum_ccdc_archive 'CCDC 908183' ####################################################################### # # 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_8 #TrackingRef '7.cif' _audit_creation_date 2012-10-26T18:34:44-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C46 H36 N2 O12' _chemical_formula_moiety 'C40 H24 O10, C4 H4 N2, 2(C H4 O)' _chemical_formula_weight 808.76 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _cell_length_a 7.6060(4) _cell_length_b 11.1161(9) _cell_length_c 12.0927(8) _cell_angle_alpha 115.965(7) _cell_angle_beta 93.139(5) _cell_angle_gamma 92.811(6) _cell_volume 914.80(11) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.35 _cell_measurement_reflns_used 4217 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour 'pale orange' _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 422 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_absorpt_correction_T_min 0.6860 _exptl_absorpt_correction_T_max 0.8965 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_unetI/netI 0.0429 _diffrn_reflns_number 5815 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD phi and omega scans' _diffrn_detector_area_resol_mean 9 _reflns_number_total 3211 _reflns_number_gt 2457 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL (Sheldrick, 2008)' _computing_molecular_graphics 'Mercury (Macrae, 2008)' _computing_publication_material 'WinGX (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0870P)^2^+0.0911P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3211 _refine_ls_number_parameters 287 _refine_ls_number_restraints 32 _refine_ls_R_factor_all 0.0721 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1496 _refine_ls_wR_factor_gt 0.1379 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.078 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.263 _refine_diff_density_min -0.626 _refine_diff_density_rms 0.059 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O3 O 0.3322(2) 0.11388(17) 0.22871(15) 0.0321(4) Uani 1 1 d . . . H3O H 0.3696 0.1129 0.2932 0.048 Uiso 1 1 calc R . . O1 O 0.16389(19) 0.66891(16) 0.25554(14) 0.0234(4) Uani 1 1 d . . . O5 O 0.1486(3) 0.98605(19) 0.82636(16) 0.0407(5) Uani 1 1 d . . . H5O H 0.2086 0.9576 0.8668 0.061 Uiso 1 1 calc R . . O2 O 0.1310(2) 0.74866(19) 0.11535(16) 0.0332(5) Uani 1 1 d . . . O4 O 0.2634(2) 0.56548(16) 0.50578(15) 0.0277(4) Uani 1 1 d . . . N1 N 0.4571(2) 0.0600(2) 0.42246(19) 0.0280(5) Uani 1 1 d . . . C2 C -0.1222(3) 0.6592(2) 0.1789(2) 0.0235(5) Uani 1 1 d . . . C7 C -0.1315(3) 0.6008(2) 0.2581(2) 0.0214(5) Uani 1 1 d . . . C14 C 0.2235(3) 0.4629(2) 0.3893(2) 0.0225(5) Uani 1 1 d . . . C12 C 0.2645(3) 0.2334(2) 0.2545(2) 0.0253(5) Uani 1 1 d . . . C9 C 0.1176(3) 0.4758(2) 0.2985(2) 0.0209(5) Uani 1 1 d . . . C15 C 0.1766(3) 0.6819(2) 0.5400(2) 0.0230(5) Uani 1 1 d . . . C5 C -0.4419(3) 0.5570(2) 0.2089(2) 0.0269(6) Uani 1 1 d . . . H5 H -0.5506 0.5201 0.216 0.032 Uiso 1 1 calc R . . C1 C 0.0640(3) 0.6990(2) 0.1759(2) 0.0229(5) Uani 1 1 d . . . C19 C -0.0084(3) 0.8285(2) 0.5026(2) 0.0256(5) Uani 1 1 d . . . H19 H -0.0809 0.8482 0.4492 0.031 Uiso 1 1 calc R . . C6 C -0.2922(3) 0.5461(2) 0.2739(2) 0.0243(5) Uani 1 1 d . . . H6 H -0.2986 0.5043 0.3256 0.029 Uiso 1 1 calc R . . C8 C 0.0501(3) 0.6091(2) 0.3213(2) 0.0214(5) Uani 1 1 d . . . C11 C 0.1597(3) 0.2435(2) 0.1605(2) 0.0262(5) Uani 1 1 d . . . H11 H 0.1388 0.1703 0.0832 0.031 Uiso 1 1 calc R . . C10 C 0.0875(3) 0.3631(2) 0.1836(2) 0.0231(5) Uani 1 1 d . . . H10 H 0.017 0.369 0.1212 0.028 Uiso 1 1 calc R . . C13 C 0.2973(3) 0.3433(2) 0.3688(2) 0.0243(5) Uani 1 1 d . . . H13 H 0.3679 0.3374 0.4312 0.029 Uiso 1 1 calc R . . C4 C -0.4334(3) 0.6220(3) 0.1332(2) 0.0288(6) Uani 1 1 d . . . H4 H -0.5369 0.6313 0.094 0.035 Uiso 1 1 calc R . . C16 C 0.2061(3) 0.7727(2) 0.6636(2) 0.0268(5) Uani 1 1 d . . . H16 H 0.2781 0.753 0.7172 0.032 Uiso 1 1 calc R . . C20 C 0.0695(3) 0.7059(2) 0.4562(2) 0.0220(5) Uani 1 1 d . . . C3 C -0.2730(3) 0.6729(3) 0.1157(2) 0.0287(6) Uani 1 1 d . . . H3 H -0.2662 0.7146 0.0639 0.034 Uiso 1 1 calc R . . C17 C 0.1274(3) 0.8927(2) 0.7065(2) 0.0292(6) Uani 1 1 d . . . C21 C 0.4428(3) -0.0730(3) 0.3822(2) 0.0299(6) Uani 1 1 d . . . H21 H 0.4034 -0.1276 0.3001 0.036 Uiso 1 1 calc R . . C22 C 0.5152(3) 0.1319(3) 0.5413(2) 0.0318(6) Uani 1 1 d . . . H22 H 0.5278 0.225 0.5735 0.038 Uiso 1 1 calc R . . C18 C 0.0191(3) 0.9204(3) 0.6246(2) 0.0294(6) Uani 1 1 d . . . H18 H -0.0341 1.0009 0.6526 0.035 Uiso 1 1 calc R . . O6A O 0.2729(4) 0.8836(3) 0.9763(3) 0.0484(9) Uani 0.713(5) 1 d PDU A 1 H6AO H 0.1975 0.8459 0.9988 0.073 Uiso 0.713(5) 1 calc PR A 1 C23A C 0.4152(5) 0.8374(5) 0.9793(4) 0.0839(12) Uani 0.713(5) 1 d PDU A 1 H23A H 0.487 0.8479 0.9208 0.126 Uiso 0.713(5) 1 calc PR A 1 H23B H 0.3957 0.7438 0.9589 0.126 Uiso 0.713(5) 1 calc PR A 1 H23C H 0.4743 0.8844 1.0607 0.126 Uiso 0.713(5) 1 calc PR A 1 O6B O 0.3731(11) 0.9466(6) 0.9804(7) 0.0469(17) Uani 0.287(5) 1 d PDU A 2 H6BO H 0.353 0.999 1.0506 0.07 Uiso 0.287(5) 1 calc PR A 2 C23B C 0.4152(5) 0.8374(5) 0.9793(4) 0.0839(12) Uani 0.287(5) 1 d PDU A 2 H23D H 0.3718 0.764 0.9019 0.126 Uiso 0.287(5) 1 calc PR A 2 H23E H 0.3642 0.8263 1.0454 0.126 Uiso 0.287(5) 1 calc PR A 2 H23F H 0.5415 0.8392 0.9898 0.126 Uiso 0.287(5) 1 calc PR A 2 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 0.0450(11) 0.0268(10) 0.0255(10) 0.0113(8) 0.0036(8) 0.0141(8) O1 0.0225(8) 0.0279(10) 0.0240(9) 0.0150(8) 0.0029(6) 0.0023(6) O5 0.0602(13) 0.0267(11) 0.0247(10) 0.0023(9) -0.0020(8) 0.0041(8) O2 0.0322(10) 0.0433(12) 0.0346(11) 0.0268(10) 0.0052(7) 0.0017(8) O4 0.0323(9) 0.0250(10) 0.0214(9) 0.0065(8) -0.0037(7) 0.0072(7) N1 0.0274(11) 0.0260(12) 0.0321(12) 0.0136(10) 0.0059(8) 0.0052(8) C2 0.0242(12) 0.0236(13) 0.0214(12) 0.0084(10) 0.0026(9) 0.0056(9) C7 0.0232(12) 0.0204(12) 0.0185(12) 0.0061(10) 0.0026(9) 0.0052(9) C14 0.0224(12) 0.0251(13) 0.0188(12) 0.0086(11) 0.0033(9) 0.0015(9) C12 0.0295(13) 0.0242(13) 0.0254(13) 0.0127(11) 0.0083(10) 0.0072(10) C9 0.0192(11) 0.0235(13) 0.0210(12) 0.0104(10) 0.0042(9) 0.0034(9) C15 0.0242(12) 0.0212(13) 0.0251(13) 0.0112(11) 0.0051(9) 0.0019(9) C5 0.0213(12) 0.0268(14) 0.0272(14) 0.0070(11) 0.0025(9) 0.0010(9) C1 0.0259(12) 0.0236(13) 0.0217(12) 0.0118(11) 0.0030(9) 0.0044(9) C19 0.0278(13) 0.0234(13) 0.0272(13) 0.0127(11) 0.0016(10) 0.0029(9) C6 0.0262(12) 0.0232(13) 0.0239(13) 0.0101(11) 0.0053(9) 0.0039(9) C8 0.0197(12) 0.0244(13) 0.0231(12) 0.0131(11) 0.0037(9) 0.0012(9) C11 0.0323(13) 0.0241(14) 0.0171(12) 0.0043(11) 0.0037(9) 0.0025(10) C10 0.0233(12) 0.0298(14) 0.0183(12) 0.0129(11) 0.0012(9) 0.0013(9) C13 0.0258(12) 0.0283(14) 0.0216(13) 0.0133(11) 0.0010(9) 0.0056(9) C4 0.0233(13) 0.0331(15) 0.0255(13) 0.0090(12) -0.0018(9) 0.0055(10) C16 0.0310(13) 0.0252(14) 0.0221(13) 0.0093(11) -0.0004(10) -0.0008(10) C20 0.0218(12) 0.0220(13) 0.0222(13) 0.0098(11) 0.0032(9) 0.0001(9) C3 0.0323(14) 0.0336(15) 0.0231(13) 0.0146(12) 0.0025(10) 0.0086(10) C17 0.0380(14) 0.0206(13) 0.0249(13) 0.0065(11) 0.0051(10) -0.0029(10) C21 0.0334(14) 0.0240(14) 0.0274(14) 0.0071(12) 0.0019(10) 0.0017(10) C22 0.0390(15) 0.0216(14) 0.0328(15) 0.0100(12) 0.0039(11) 0.0026(10) C18 0.0361(14) 0.0212(13) 0.0303(14) 0.0101(11) 0.0067(10) 0.0052(10) O6A 0.0598(16) 0.0483(15) 0.0423(14) 0.0257(11) 0.0041(11) -0.0035(12) C23A 0.0891(17) 0.0838(17) 0.0815(17) 0.0394(13) 0.0104(12) 0.0000(13) O6B 0.048(2) 0.048(2) 0.045(2) 0.0210(16) 0.0008(16) 0.0103(17) C23B 0.0891(17) 0.0838(17) 0.0815(17) 0.0394(13) 0.0104(12) 0.0000(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C12 1.360(3) . ? O3 H3O 0.82 . ? O1 C1 1.358(3) . ? O1 C8 1.518(3) . ? O5 C17 1.359(3) . ? O5 H5O 0.82 . ? O2 C1 1.212(3) . ? O4 C14 1.374(3) . ? O4 C15 1.388(3) . ? N1 C21 1.335(3) . ? N1 C22 1.338(3) . ? C2 C7 1.376(3) . ? C2 C3 1.395(3) . ? C2 C1 1.470(3) . ? C7 C6 1.398(3) . ? C7 C8 1.519(3) . ? C14 C9 1.388(3) . ? C14 C13 1.393(3) . ? C12 C13 1.385(3) . ? C12 C11 1.401(3) . ? C9 C10 1.402(3) . ? C9 C8 1.507(3) . ? C15 C16 1.386(3) . ? C15 C20 1.389(3) . ? C5 C6 1.389(3) . ? C5 C4 1.394(3) . ? C5 H5 0.93 . ? C19 C18 1.374(3) . ? C19 C20 1.404(3) . ? C19 H19 0.93 . ? C6 H6 0.93 . ? C8 C20 1.504(3) . ? C11 C10 1.382(3) . ? C11 H11 0.93 . ? C10 H10 0.93 . ? C13 H13 0.93 . ? C4 C3 1.385(4) . ? C4 H4 0.93 . ? C16 C17 1.384(3) . ? C16 H16 0.93 . ? C3 H3 0.93 . ? C17 C18 1.399(4) . ? C21 C22 1.381(4) 2_656 ? C21 H21 0.93 . ? C22 C21 1.381(4) 2_656 ? C22 H22 0.93 . ? C18 H18 0.93 . ? O6A C23A 1.226(4) . ? O6A H6AO 0.82 . ? C23A H23A 0.96 . ? C23A H23B 0.96 . ? C23A H23C 0.96 . ? O6B H6BO 0.82 . ? 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 C12 O3 H3O 109.5 . . ? C1 O1 C8 111.32(16) . . ? C17 O5 H5O 109.5 . . ? C14 O4 C15 118.68(17) . . ? C21 N1 C22 115.6(2) . . ? C7 C2 C3 121.8(2) . . ? C7 C2 C1 108.60(19) . . ? C3 C2 C1 129.6(2) . . ? C2 C7 C6 121.2(2) . . ? C2 C7 C8 110.35(19) . . ? C6 C7 C8 128.4(2) . . ? O4 C14 C9 123.2(2) . . ? O4 C14 C13 114.75(19) . . ? C9 C14 C13 122.1(2) . . ? O3 C12 C13 122.2(2) . . ? O3 C12 C11 117.7(2) . . ? C13 C12 C11 120.0(2) . . ? C14 C9 C10 117.3(2) . . ? C14 C9 C8 120.5(2) . . ? C10 C9 C8 122.01(19) . . ? C16 C15 O4 115.0(2) . . ? C16 C15 C20 122.7(2) . . ? O4 C15 C20 122.3(2) . . ? C6 C5 C4 121.7(2) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? O2 C1 O1 121.2(2) . . ? O2 C1 C2 130.3(2) . . ? O1 C1 C2 108.57(19) . . ? C18 C19 C20 122.0(2) . . ? C18 C19 H19 119 . . ? C20 C19 H19 119 . . ? C5 C6 C7 117.0(2) . . ? C5 C6 H6 121.5 . . ? C7 C6 H6 121.5 . . ? C20 C8 C9 111.73(18) . . ? C20 C8 C7 113.77(18) . . ? C9 C8 C7 114.95(19) . . ? C20 C8 O1 107.21(17) . . ? C9 C8 O1 107.18(16) . . ? C7 C8 O1 100.88(16) . . ? C10 C11 C12 119.4(2) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C11 C10 C9 121.9(2) . . ? C11 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? C12 C13 C14 119.4(2) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C3 C4 C5 120.9(2) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C17 C16 C15 119.4(2) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C15 C20 C19 116.5(2) . . ? C15 C20 C8 121.1(2) . . ? C19 C20 C8 122.2(2) . . ? C4 C3 C2 117.4(2) . . ? C4 C3 H3 121.3 . . ? C2 C3 H3 121.3 . . ? O5 C17 C16 122.9(2) . . ? O5 C17 C18 117.6(2) . . ? C16 C17 C18 119.5(2) . . ? N1 C21 C22 121.9(2) . 2_656 ? N1 C21 H21 119 . . ? C22 C21 H21 119 2_656 . ? N1 C22 C21 122.4(2) . 2_656 ? N1 C22 H22 118.8 . . ? C21 C22 H22 118.8 2_656 . ? C19 C18 C17 119.9(2) . . ? C19 C18 H18 120 . . ? C17 C18 H18 120 . . ? _vrf_DIFMN02_7 ; PROBLEM: The minimum difference density is < -0.1*ZMAX*0.75 _refine_diff_density_min given = -0.626 Test value = -0.600 RESPONSE: The nearest atom to this minimum is H23E and its distance to the minimum is 0.37 A. ; _vrf_DIFMN03_7 ; PROBLEM: The minimum difference density is < -0.1*ZMAX*0.75 The relevant atom site should be identified. RESPONSE: The nearest atom to this minimum is H23E and its distance to the minimum is 0.37 A. ; _vrf_Plat098_7 ; PROBLEM: Large Reported Min. (Negative) Residual Density -0.63 eA-3 RESPONSE: The nearest atom to this minimum is H23E and its distance to the minimum is 0.37 A. ; _database_code_depnum_ccdc_archive 'CCDC 908184'