# Electronic Supplementary Material (ESI) for RSC Advances # 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_ab_313 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C24 H17 N O4' _chemical_formula_sum 'C24 H17 N O4' _chemical_compound_source synthesis _exptl_crystal_recrystallization_method ethylacetate _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour colorless _diffrn_ambient_temperature 296(2) _chemical_formula_weight 383.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2208(3) _cell_length_b 12.7931(5) _cell_length_c 13.3551(5) _cell_angle_alpha 113.491(2) _cell_angle_beta 91.551(2) _cell_angle_gamma 97.433(2) _cell_volume 962.95(7) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.955 _exptl_absorpt_correction_T_max 0.973 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8491 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 19.41 _reflns_number_total 1645 _reflns_number_gt 1333 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0544P)^2^+0.0503P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1645 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0893 _refine_ls_wR_factor_gt 0.0825 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C20 C 0.1575(4) 1.0359(2) 0.37979(17) 0.0437(6) Uani 1 1 d . . . C18 C -0.0302(4) 0.8078(2) 0.32416(17) 0.0429(6) Uani 1 1 d . . . C19 C 0.2832(4) 0.9553(2) 0.38248(18) 0.0488(7) Uani 1 1 d . . . H19 H 0.4317 0.9773 0.4028 0.059 Uiso 1 1 calc R . . C16 C -0.1437(5) 0.6888(2) 0.30063(19) 0.0509(7) Uani 1 1 d . . . C5 C -0.0171(4) 0.5912(2) 0.2792(2) 0.0493(7) Uani 1 1 d . . . C17 C 0.1898(4) 0.8420(2) 0.35524(18) 0.0486(7) Uani 1 1 d . . . H17 H 0.2759 0.7887 0.3579 0.058 Uiso 1 1 calc R . . C22 C -0.1548(4) 0.8887(2) 0.32045(19) 0.0554(7) Uani 1 1 d . . . H22 H -0.3028 0.8664 0.2988 0.066 Uiso 1 1 calc R . . C6 C 0.1341(4) 0.5619(2) 0.2008(2) 0.0495(7) Uani 1 1 d . . . C23 C 0.2507(5) 1.1588(2) 0.41084(19) 0.0539(7) Uani 1 1 d . . . C21 C -0.0632(4) 1.0012(2) 0.34816(19) 0.0560(7) Uani 1 1 d . . . H21 H -0.1496 1.0544 0.3457 0.067 Uiso 1 1 calc R . . C2 C 0.2530(4) 0.4744(2) 0.1921(2) 0.0640(8) Uani 1 1 d . . . H2 H 0.3546 0.4548 0.1405 0.077 Uiso 1 1 calc R . . C9 C 0.3012(5) 0.7108(2) 0.0272(2) 0.0527(7) Uani 1 1 d . . . C4 C -0.0504(4) 0.5291(2) 0.3444(2) 0.0634(7) Uani 1 1 d . . . H4 H -0.1544 0.5464 0.3949 0.076 Uiso 1 1 calc R . . C7 C 0.1649(5) 0.62013(19) 0.12582(19) 0.0501(7) Uani 1 1 d . . . C11 C 0.6373(5) 0.8150(2) 0.0003(2) 0.0701(8) Uani 1 1 d . . . H11 H 0.7084 0.7991 0.0536 0.084 Uiso 1 1 calc R . . C8 C 0.3596(4) 0.6553(2) 0.0878(2) 0.0563(7) Uani 1 1 d . . . H8 H 0.4989 0.6427 0.1020 0.068 Uiso 1 1 calc R . . C10 C 0.4177(5) 0.7745(2) -0.0291(2) 0.0567(7) Uani 1 1 d . . . C15 C 0.3159(5) 0.7979(3) -0.1096(2) 0.0768(8) Uani 1 1 d . . . H15 H 0.1693 0.7696 -0.1319 0.092 Uiso 1 1 calc R . . C3 C 0.0685(5) 0.4429(2) 0.3347(3) 0.0739(8) Uani 1 1 d . . . H3 H 0.0458 0.4024 0.3789 0.089 Uiso 1 1 calc R . . C24 C 0.5755(4) 1.2953(2) 0.4616(2) 0.0787(9) Uani 1 1 d . . . H24A H 0.5354 1.3231 0.4078 0.118 Uiso 1 1 calc R . . H24B H 0.7303 1.2972 0.4667 0.118 Uiso 1 1 calc R . . H24C H 0.5319 1.3433 0.5314 0.118 Uiso 1 1 calc R . . C12 C 0.7510(5) 0.8784(3) -0.0485(3) 0.0894(10) Uani 1 1 d . . . H12 H 0.8991 0.9042 -0.0290 0.107 Uiso 1 1 calc R . . C13 C 0.6482(9) 0.9039(3) -0.1255(3) 0.0982(11) Uani 1 1 d . . . H13 H 0.7253 0.9489 -0.1566 0.118 Uiso 1 1 calc R . . C1 C 0.2218(5) 0.4164(2) 0.2592(3) 0.0734(9) Uani 1 1 d . . . H1 H 0.3046 0.3591 0.2537 0.088 Uiso 1 1 calc R . . C14 C 0.4322(8) 0.8635(3) -0.1570(3) 0.0968(11) Uani 1 1 d . . . H14 H 0.3631 0.8800 -0.2104 0.116 Uiso 1 1 calc R . . N1 N -0.0041(3) 0.64945(17) 0.08786(17) 0.0592(6) Uani 1 1 d . . . O3 O 0.4678(3) 1.17755(13) 0.42947(13) 0.0639(5) Uani 1 1 d . . . O2 O -0.3401(3) 0.67343(14) 0.30705(15) 0.0724(6) Uani 1 1 d . . . O4 O 0.1452(3) 1.23347(15) 0.41844(16) 0.0795(6) Uani 1 1 d . . . O1 O 0.0817(3) 0.70851(14) 0.02486(13) 0.0627(5) 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 C20 0.0464(18) 0.0393(18) 0.0468(16) 0.0164(12) 0.0073(13) 0.0146(15) C18 0.0418(17) 0.0412(17) 0.0461(15) 0.0165(12) 0.0057(12) 0.0113(15) C19 0.0402(15) 0.0462(18) 0.0565(17) 0.0172(13) 0.0017(12) 0.0077(15) C16 0.0482(19) 0.054(2) 0.0506(16) 0.0215(13) 0.0022(14) 0.0068(17) C5 0.0502(17) 0.0384(16) 0.0541(17) 0.0164(14) -0.0024(14) -0.0013(14) C17 0.0462(19) 0.0436(19) 0.0563(16) 0.0187(13) 0.0005(13) 0.0130(14) C22 0.0411(16) 0.0558(19) 0.0675(18) 0.0225(15) 0.0027(13) 0.0099(16) C6 0.0547(17) 0.0354(16) 0.0534(18) 0.0147(14) -0.0054(15) 0.0025(14) C23 0.060(2) 0.048(2) 0.0572(17) 0.0235(14) 0.0067(14) 0.0130(18) C21 0.050(2) 0.050(2) 0.0724(19) 0.0249(14) 0.0038(14) 0.0205(15) C2 0.074(2) 0.0450(17) 0.067(2) 0.0171(16) 0.0012(15) 0.0089(16) C9 0.046(2) 0.0541(17) 0.0525(18) 0.0146(15) 0.0019(14) 0.0123(14) C4 0.0700(19) 0.0512(18) 0.070(2) 0.0273(16) 0.0052(14) 0.0034(16) C7 0.055(2) 0.0395(16) 0.0482(17) 0.0091(13) 0.0000(16) 0.0103(14) C11 0.071(2) 0.070(2) 0.075(2) 0.0325(17) 0.0139(18) 0.0155(17) C8 0.053(2) 0.0592(17) 0.0590(18) 0.0250(15) 0.0014(15) 0.0144(15) C10 0.068(2) 0.0535(17) 0.0518(18) 0.0210(15) 0.0102(16) 0.0196(16) C15 0.087(2) 0.091(2) 0.064(2) 0.0386(19) 0.0146(19) 0.0275(19) C3 0.094(2) 0.051(2) 0.081(2) 0.0333(16) -0.001(2) 0.0033(18) C24 0.076(2) 0.0524(19) 0.102(2) 0.0311(16) 0.0047(17) -0.0087(16) C12 0.093(3) 0.077(2) 0.096(3) 0.032(2) 0.032(2) 0.012(2) C13 0.136(4) 0.071(2) 0.100(3) 0.041(2) 0.053(3) 0.028(3) C1 0.089(2) 0.0441(18) 0.085(2) 0.0232(18) -0.007(2) 0.0141(16) C14 0.141(4) 0.104(3) 0.071(2) 0.051(2) 0.033(3) 0.052(3) N1 0.0555(16) 0.0629(15) 0.0590(15) 0.0250(12) 0.0020(12) 0.0080(12) O3 0.0569(13) 0.0493(13) 0.0833(13) 0.0268(9) 0.0029(10) 0.0015(9) O2 0.0476(12) 0.0746(13) 0.0987(15) 0.0410(11) 0.0068(10) 0.0019(10) O4 0.0751(14) 0.0516(12) 0.1185(16) 0.0385(11) 0.0053(11) 0.0204(11) O1 0.0586(14) 0.0760(12) 0.0608(12) 0.0341(10) 0.0012(9) 0.0154(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C20 C19 1.383(3) . ? C20 C21 1.386(3) . ? C20 C23 1.488(3) . ? C18 C17 1.381(3) . ? C18 C22 1.386(3) . ? C18 C16 1.497(3) . ? C19 C17 1.386(3) . ? C16 O2 1.223(2) . ? C16 C5 1.498(3) . ? C5 C4 1.396(3) . ? C5 C6 1.398(3) . ? C22 C21 1.374(3) . ? C6 C2 1.390(3) . ? C6 C7 1.470(3) . ? C23 O4 1.200(3) . ? C23 O3 1.339(3) . ? C2 C1 1.375(3) . ? C9 C8 1.342(3) . ? C9 O1 1.361(3) . ? C9 C10 1.456(3) . ? C4 C3 1.373(3) . ? C7 N1 1.314(3) . ? C7 C8 1.415(3) . ? C11 C12 1.371(4) . ? C11 C10 1.384(3) . ? C10 C15 1.384(3) . ? C15 C14 1.385(4) . ? C3 C1 1.380(3) . ? C24 O3 1.452(3) . ? C12 C13 1.363(4) . ? C13 C14 1.366(4) . ? N1 O1 1.411(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C19 C20 C21 118.9(2) . . ? C19 C20 C23 122.2(3) . . ? C21 C20 C23 118.9(2) . . ? C17 C18 C22 118.7(2) . . ? C17 C18 C16 123.0(2) . . ? C22 C18 C16 118.1(2) . . ? C20 C19 C17 120.6(2) . . ? O2 C16 C5 119.8(2) . . ? O2 C16 C18 119.3(2) . . ? C5 C16 C18 120.8(2) . . ? C4 C5 C6 119.2(2) . . ? C4 C5 C16 117.0(3) . . ? C6 C5 C16 123.8(2) . . ? C18 C17 C19 120.4(2) . . ? C21 C22 C18 121.1(2) . . ? C2 C6 C5 119.2(2) . . ? C2 C6 C7 119.7(3) . . ? C5 C6 C7 121.1(2) . . ? O4 C23 O3 123.3(2) . . ? O4 C23 C20 124.4(3) . . ? O3 C23 C20 112.3(2) . . ? C22 C21 C20 120.3(2) . . ? C1 C2 C6 120.6(3) . . ? C8 C9 O1 108.9(2) . . ? C8 C9 C10 134.9(3) . . ? O1 C9 C10 116.0(2) . . ? C3 C4 C5 120.8(3) . . ? N1 C7 C8 111.3(2) . . ? N1 C7 C6 119.5(3) . . ? C8 C7 C6 129.2(3) . . ? C12 C11 C10 120.5(3) . . ? C9 C8 C7 105.6(2) . . ? C15 C10 C11 118.8(3) . . ? C15 C10 C9 122.4(3) . . ? C11 C10 C9 118.9(3) . . ? C10 C15 C14 120.0(3) . . ? C4 C3 C1 119.7(3) . . ? C13 C12 C11 120.4(3) . . ? C12 C13 C14 120.2(3) . . ? C2 C1 C3 120.4(3) . . ? C13 C14 C15 120.2(3) . . ? C7 N1 O1 105.25(19) . . ? C23 O3 C24 116.82(19) . . ? C9 O1 N1 108.87(18) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 19.41 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.136 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.029 _database_code_depnum_ccdc_archive 'CCDC 945394' ####################################################################### # # 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_ab-318 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C23 H17 N O3' _chemical_formula_sum 'C23 H17 N O3' _chemical_compound_source synthesis _chemical_melting_point ? _exptl_crystal_description needle _exptl_crystal_colour colorless _diffrn_ambient_temperature 296(2) _chemical_formula_weight 355.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _symmetry_space_group_name_Hall '-P 1 ' _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8993(11) _cell_length_b 10.4759(13) _cell_length_c 11.0032(14) _cell_angle_alpha 70.643(7) _cell_angle_beta 72.001(5) _cell_angle_gamma 73.148(7) _cell_volume 900.14(19) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.971 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9621 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0558 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2964 _reflns_number_gt 2188 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+20.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.034(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2964 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1980 _refine_ls_R_factor_gt 0.1770 _refine_ls_wR_factor_ref 0.4315 _refine_ls_wR_factor_gt 0.4251 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.131 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.4231(10) 0.4168(8) -0.1320(8) 0.049(2) Uani 1 1 d . . . N1 N 0.4387(12) 0.3411(10) -0.0019(10) 0.049(3) Uani 1 1 d . . . O2 O 0.2925(11) 0.0678(10) 0.1842(10) 0.064(3) Uani 1 1 d . . . O3 O 1.0340(10) -0.2084(9) 0.1203(9) 0.057(3) Uani 1 1 d . . . C5 C 0.5655(15) 0.0175(12) 0.1970(12) 0.044(3) Uani 1 1 d . . . C2 C 0.8851(14) -0.1259(12) 0.1453(12) 0.041(3) Uani 1 1 d . . . C7 C 0.8466(15) -0.0169(12) 0.1940(13) 0.047(3) Uani 1 1 d . . . H7 H 0.9268 0.0091 0.2127 0.057 Uiso 1 1 calc R . . C3 C 0.7612(13) -0.1701(12) 0.1247(13) 0.044(3) Uani 1 1 d . . . H3 H 0.7859 -0.2497 0.0964 0.053 Uiso 1 1 calc R . . C6 C 0.6894(14) 0.0586(12) 0.2173(12) 0.042(3) Uani 1 1 d . . . H6 H 0.6664 0.1373 0.2467 0.051 Uiso 1 1 calc R . . C17 C 0.2902(13) 0.5174(12) -0.1267(12) 0.041(3) Uani 1 1 d . . . C8 C 0.3967(15) 0.0966(13) 0.2174(12) 0.047(3) Uani 1 1 d . . . C14 C 0.2943(14) 0.3501(12) 0.2207(13) 0.044(3) Uani 1 1 d . . . C18 C 0.2552(15) 0.6114(13) -0.2504(13) 0.047(3) Uani 1 1 d . . . C19 C 0.1080(16) 0.7064(13) -0.2529(13) 0.053(3) Uani 1 1 d . . . H19 H 0.0299 0.7072 -0.1740 0.064 Uiso 1 1 calc R . . C15 C 0.3144(13) 0.3983(11) 0.0804(13) 0.040(3) Uani 1 1 d . . . C20 C 0.0758(17) 0.7977(15) -0.3673(15) 0.064(4) Uani 1 1 d . . . H20 H -0.0236 0.8591 -0.3662 0.077 Uiso 1 1 calc R . . C4 C 0.6086(16) -0.0983(12) 0.1457(12) 0.047(3) Uani 1 1 d . . . H4 H 0.5298 -0.1251 0.1261 0.056 Uiso 1 1 calc R . . C16 C 0.2176(15) 0.5087(12) 0.0022(13) 0.045(3) Uani 1 1 d . . . H16 H 0.1212 0.5647 0.0345 0.053 Uiso 1 1 calc R . . C1 C 1.1646(16) -0.1688(15) 0.1400(15) 0.059(4) Uani 1 1 d . . . H1A H 1.1604 -0.0719 0.0985 0.089 Uiso 1 1 calc R . . H1B H 1.2656 -0.2211 0.1015 0.089 Uiso 1 1 calc R . . H1C H 1.1549 -0.1870 0.2332 0.089 Uiso 1 1 calc R . . C9 C 0.3451(15) 0.2109(13) 0.2856(13) 0.049(3) Uani 1 1 d . . . C10 C 0.3319(17) 0.1697(14) 0.4238(13) 0.054(3) Uani 1 1 d . . . H10 H 0.3691 0.0778 0.4661 0.065 Uiso 1 1 calc R . . C13 C 0.2229(17) 0.4433(15) 0.2962(15) 0.062(4) Uani 1 1 d . . . H13 H 0.1843 0.5350 0.2548 0.074 Uiso 1 1 calc R . . C22 C 0.3363(19) 0.7044(17) -0.4901(14) 0.072(5) Uani 1 1 d . . . H22 H 0.4123 0.7019 -0.5697 0.087 Uiso 1 1 calc R . . C21 C 0.192(2) 0.7991(14) -0.4868(14) 0.064(4) Uani 1 1 d . . . H21 H 0.1722 0.8645 -0.5643 0.077 Uiso 1 1 calc R . . C23 C 0.3661(19) 0.6096(16) -0.3677(15) 0.068(4) Uani 1 1 d . . . H23 H 0.4635 0.5454 -0.3683 0.082 Uiso 1 1 calc R . . C12 C 0.2069(19) 0.4042(15) 0.4320(15) 0.068(4) Uani 1 1 d . . . H12 H 0.1587 0.4698 0.4800 0.082 Uiso 1 1 calc R . . C11 C 0.2624(18) 0.2683(16) 0.4967(14) 0.065(4) Uani 1 1 d . . . H11 H 0.2536 0.2427 0.5876 0.078 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.049(5) 0.042(5) 0.036(5) 0.001(4) -0.001(4) -0.003(4) N1 0.044(6) 0.041(6) 0.052(7) -0.007(5) -0.010(5) 0.000(5) O2 0.054(6) 0.062(6) 0.081(7) -0.026(5) -0.019(5) -0.007(5) O3 0.045(5) 0.057(6) 0.072(6) -0.038(5) -0.005(5) -0.004(4) C5 0.056(8) 0.038(7) 0.034(7) -0.004(5) -0.009(6) -0.009(6) C2 0.046(7) 0.037(6) 0.039(7) -0.014(5) -0.011(5) -0.001(5) C7 0.047(7) 0.044(7) 0.055(8) -0.012(6) -0.023(6) -0.005(6) C3 0.036(7) 0.031(6) 0.067(9) -0.022(6) -0.010(6) -0.001(5) C6 0.049(7) 0.034(6) 0.047(7) -0.013(5) -0.010(6) -0.013(5) C17 0.027(6) 0.040(7) 0.047(7) -0.010(6) -0.001(5) -0.002(5) C8 0.047(7) 0.054(8) 0.042(7) -0.010(6) -0.019(6) -0.008(6) C14 0.036(6) 0.038(7) 0.058(8) -0.014(6) -0.009(6) -0.010(5) C18 0.048(7) 0.040(7) 0.050(8) -0.006(6) -0.009(6) -0.013(6) C19 0.057(8) 0.045(7) 0.048(8) 0.003(6) -0.022(6) -0.004(6) C15 0.032(6) 0.027(6) 0.060(8) -0.015(6) -0.006(5) -0.006(5) C20 0.051(8) 0.067(9) 0.065(10) -0.006(8) -0.025(7) 0.003(7) C4 0.061(8) 0.043(7) 0.043(7) -0.014(6) -0.010(6) -0.019(6) C16 0.042(7) 0.034(6) 0.055(8) -0.016(6) -0.008(6) -0.002(5) C1 0.044(8) 0.064(9) 0.068(10) -0.012(7) -0.015(7) -0.012(7) C9 0.051(8) 0.047(7) 0.050(8) -0.018(6) -0.002(6) -0.016(6) C10 0.066(9) 0.048(8) 0.042(8) -0.003(6) -0.010(7) -0.017(7) C13 0.057(9) 0.051(8) 0.066(10) -0.009(7) -0.013(7) -0.003(7) C22 0.072(10) 0.087(11) 0.036(8) -0.013(7) -0.014(7) 0.012(9) C21 0.097(12) 0.050(8) 0.038(8) -0.001(6) -0.033(8) 0.000(8) C23 0.059(9) 0.070(10) 0.063(10) -0.014(8) -0.005(8) -0.008(8) C12 0.078(11) 0.057(9) 0.059(10) -0.032(8) 0.014(8) -0.011(8) C11 0.073(10) 0.076(11) 0.044(8) -0.025(8) -0.005(7) -0.012(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C17 1.338(13) . ? O1 N1 1.415(13) . ? N1 C15 1.327(15) . ? O2 C8 1.236(14) . ? O3 C2 1.359(14) . ? O3 C1 1.437(15) . ? C5 C6 1.394(16) . ? C5 C4 1.410(16) . ? C5 C8 1.479(17) . ? C2 C7 1.332(16) . ? C2 C3 1.415(16) . ? C7 C6 1.386(16) . ? C3 C4 1.339(16) . ? C17 C16 1.349(17) . ? C17 C18 1.454(17) . ? C8 C9 1.508(17) . ? C14 C13 1.378(18) . ? C14 C9 1.402(17) . ? C14 C15 1.427(18) . ? C18 C23 1.364(19) . ? C18 C19 1.398(17) . ? C19 C20 1.359(18) . ? C15 C16 1.429(16) . ? C20 C21 1.40(2) . ? C9 C10 1.412(18) . ? C10 C11 1.403(18) . ? C13 C12 1.38(2) . ? C22 C21 1.37(2) . ? C22 C23 1.43(2) . ? C12 C11 1.38(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C17 O1 N1 109.7(9) . . ? C15 N1 O1 106.8(9) . . ? C2 O3 C1 116.8(10) . . ? C6 C5 C4 117.3(11) . . ? C6 C5 C8 122.5(11) . . ? C4 C5 C8 120.0(12) . . ? C7 C2 O3 126.4(11) . . ? C7 C2 C3 119.2(11) . . ? O3 C2 C3 114.3(10) . . ? C2 C7 C6 121.2(12) . . ? C4 C3 C2 120.6(11) . . ? C7 C6 C5 120.5(11) . . ? O1 C17 C16 107.7(10) . . ? O1 C17 C18 118.6(10) . . ? C16 C17 C18 133.7(11) . . ? O2 C8 C5 121.4(12) . . ? O2 C8 C9 118.0(11) . . ? C5 C8 C9 120.5(11) . . ? C13 C14 C9 118.3(12) . . ? C13 C14 C15 119.1(11) . . ? C9 C14 C15 122.6(11) . . ? C23 C18 C19 118.0(13) . . ? C23 C18 C17 120.6(12) . . ? C19 C18 C17 121.3(12) . . ? C20 C19 C18 121.9(14) . . ? N1 C15 C14 121.9(11) . . ? N1 C15 C16 107.7(11) . . ? C14 C15 C16 130.4(11) . . ? C19 C20 C21 119.9(13) . . ? C3 C4 C5 121.0(12) . . ? C17 C16 C15 108.2(10) . . ? C14 C9 C10 120.5(12) . . ? C14 C9 C8 122.7(12) . . ? C10 C9 C8 116.4(11) . . ? C11 C10 C9 119.4(13) . . ? C14 C13 C12 121.9(13) . . ? C21 C22 C23 118.2(14) . . ? C22 C21 C20 120.3(13) . . ? C18 C23 C22 121.5(14) . . ? C11 C12 C13 120.5(13) . . ? C12 C11 C10 119.3(13) . . ? _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.936 _refine_diff_density_max 0.755 _refine_diff_density_min -0.491 _refine_diff_density_rms 0.139 _database_code_depnum_ccdc_archive 'CCDC 945395'