# Electronic Supplementary Material (ESI) for Chemical Communications # 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_3a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H16 N2 O4' _chemical_formula_sum 'C16 H16 N2 O4' _chemical_formula_weight 300.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9815(8) _cell_length_b 9.9504(10) _cell_length_c 10.0645(10) _cell_angle_alpha 96.580(2) _cell_angle_beta 101.994(2) _cell_angle_gamma 100.214(2) _cell_volume 759.89(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.008 _exptl_crystal_size_mid 0.006 _exptl_crystal_size_min 0.002 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.56258 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3962 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.19 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2615 _reflns_number_gt 2175 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0703P)^2^+0.3827P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2615 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1344 _refine_ls_wR_factor_gt 0.1192 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.20466(19) 0.42118(14) 0.48698(16) 0.0287(4) Uani 1 1 d . . . O2 O 0.07220(18) 0.23538(14) 0.56086(14) 0.0231(4) Uani 1 1 d . . . O3 O 0.3167(2) 0.00085(14) 0.56671(15) 0.0291(4) Uani 1 1 d . . . O4 O 0.45991(19) 0.20690(14) 0.68870(14) 0.0254(4) Uani 1 1 d . . . N1 N 0.1550(2) 0.12354(19) -0.03553(19) 0.0311(5) Uani 1 1 d . . . N2 N 0.0896(2) 0.02030(17) 0.30615(17) 0.0230(4) Uani 1 1 d . . . H2A H 0.0320 -0.0195 0.2251 0.028 Uiso 1 1 calc R . . H2B H 0.0630 -0.0100 0.3773 0.028 Uiso 1 1 calc R . . C1 C 0.6183(3) 0.4598(2) 0.1572(2) 0.0256(5) Uani 1 1 d . . . H1 H 0.5512 0.5270 0.1606 0.031 Uiso 1 1 calc R . . C2 C 0.7585(3) 0.4783(2) 0.0940(2) 0.0314(5) Uani 1 1 d . . . H2 H 0.7845 0.5578 0.0555 0.038 Uiso 1 1 calc R . . C3 C 0.8591(3) 0.3790(2) 0.0882(2) 0.0301(5) Uani 1 1 d . . . H3 H 0.9526 0.3913 0.0459 0.036 Uiso 1 1 calc R . . C4 C 0.8196(3) 0.2613(2) 0.1460(2) 0.0278(5) Uani 1 1 d . . . H4 H 0.8867 0.1941 0.1420 0.033 Uiso 1 1 calc R . . C5 C 0.6818(3) 0.2427(2) 0.2093(2) 0.0236(5) Uani 1 1 d . . . H5 H 0.6576 0.1633 0.2485 0.028 Uiso 1 1 calc R . . C6 C 0.5781(3) 0.34125(19) 0.21544(19) 0.0198(4) Uani 1 1 d . . . C7 C 0.4275(2) 0.3225(2) 0.2856(2) 0.0206(4) Uani 1 1 d . . . H7 H 0.3752 0.4045 0.2832 0.025 Uiso 1 1 calc R . . C8 C 0.2842(2) 0.19377(19) 0.2243(2) 0.0193(4) Uani 1 1 d . . . C9 C 0.2210(2) 0.12969(19) 0.32161(19) 0.0186(4) Uani 1 1 d . . . C10 C 0.3146(2) 0.21071(19) 0.46408(19) 0.0182(4) Uani 1 1 d . . . C11 C 0.4795(2) 0.2983(2) 0.4361(2) 0.0197(4) Uani 1 1 d . . . H11A H 0.5752 0.2495 0.4484 0.024 Uiso 1 1 calc R . . H11B H 0.5156 0.3857 0.4982 0.024 Uiso 1 1 calc R . . C12 C 0.2136(3) 0.1543(2) 0.0815(2) 0.0217(5) Uani 1 1 d . . . C13 C 0.1933(3) 0.3039(2) 0.5059(2) 0.0200(4) Uani 1 1 d . . . C14 C 0.3610(2) 0.12416(19) 0.5768(2) 0.0187(4) Uani 1 1 d . . . C15 C -0.0553(3) 0.3146(2) 0.5932(2) 0.0280(5) Uani 1 1 d . . . H15A H 0.0038 0.3949 0.6598 0.042 Uiso 1 1 calc R . . H15B H -0.1394 0.2583 0.6302 0.042 Uiso 1 1 calc R . . H15C H -0.1141 0.3428 0.5110 0.042 Uiso 1 1 calc R . . C16 C 0.5139(3) 0.1416(2) 0.8080(2) 0.0298(5) Uani 1 1 d . . . H16A H 0.4122 0.0955 0.8340 0.045 Uiso 1 1 calc R . . H16B H 0.5834 0.2107 0.8829 0.045 Uiso 1 1 calc R . . H16C H 0.5819 0.0754 0.7857 0.045 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 0.0294(8) 0.0193(8) 0.0389(9) 0.0059(6) 0.0107(7) 0.0047(6) O2 0.0210(7) 0.0221(7) 0.0287(8) 0.0056(6) 0.0091(6) 0.0061(6) O3 0.0366(9) 0.0204(8) 0.0259(8) 0.0056(6) -0.0001(7) 0.0020(6) O4 0.0328(8) 0.0215(7) 0.0173(7) 0.0030(6) -0.0027(6) 0.0038(6) N1 0.0276(10) 0.0366(11) 0.0243(11) 0.0025(8) 0.0057(8) -0.0046(8) N2 0.0228(9) 0.0232(9) 0.0187(9) 0.0028(7) 0.0021(7) -0.0031(7) C1 0.0277(11) 0.0223(11) 0.0263(11) 0.0057(9) 0.0054(9) 0.0038(8) C2 0.0326(12) 0.0282(12) 0.0346(13) 0.0131(10) 0.0121(10) -0.0009(9) C3 0.0229(11) 0.0372(13) 0.0296(12) 0.0072(10) 0.0088(9) 0.0004(9) C4 0.0218(11) 0.0311(12) 0.0292(12) 0.0038(9) 0.0045(9) 0.0050(9) C5 0.0256(11) 0.0223(10) 0.0227(11) 0.0058(8) 0.0056(9) 0.0030(8) C6 0.0201(10) 0.0200(10) 0.0155(10) 0.0017(8) 0.0008(8) -0.0012(8) C7 0.0182(10) 0.0189(10) 0.0231(10) 0.0015(8) 0.0041(8) 0.0020(8) C8 0.0165(10) 0.0198(10) 0.0196(10) 0.0021(8) 0.0025(8) 0.0011(8) C9 0.0166(10) 0.0180(10) 0.0197(10) 0.0005(8) 0.0018(8) 0.0045(7) C10 0.0195(10) 0.0154(9) 0.0178(10) 0.0012(8) 0.0026(8) 0.0013(8) C11 0.0174(10) 0.0191(10) 0.0202(10) 0.0016(8) 0.0026(8) 0.0001(8) C12 0.0187(10) 0.0219(10) 0.0236(12) 0.0040(8) 0.0056(9) 0.0007(8) C13 0.0189(10) 0.0208(10) 0.0173(10) 0.0004(8) 0.0005(8) 0.0020(8) C14 0.0155(10) 0.0193(10) 0.0205(10) 0.0016(8) 0.0044(8) 0.0025(7) C15 0.0229(11) 0.0274(11) 0.0359(12) 0.0038(9) 0.0102(9) 0.0076(9) C16 0.0357(13) 0.0303(12) 0.0203(11) 0.0062(9) -0.0014(9) 0.0063(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C13 1.195(2) . ? O2 C13 1.334(2) . ? O2 C15 1.458(2) . ? O3 C14 1.201(2) . ? O4 C14 1.325(2) . ? O4 C16 1.453(2) . ? N1 C12 1.157(3) . ? N2 C9 1.341(2) . ? C1 C2 1.393(3) . ? C1 C6 1.393(3) . ? C2 C3 1.383(3) . ? C3 C4 1.382(3) . ? C4 C5 1.377(3) . ? C5 C6 1.396(3) . ? C6 C7 1.510(3) . ? C7 C8 1.528(3) . ? C7 C11 1.544(3) . ? C8 C9 1.361(3) . ? C8 C12 1.412(3) . ? C9 C10 1.530(3) . ? C10 C14 1.526(3) . ? C10 C13 1.540(3) . ? C10 C11 1.541(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O2 C15 114.16(15) . . ? C14 O4 C16 116.44(15) . . ? C2 C1 C6 120.44(19) . . ? C3 C2 C1 120.3(2) . . ? C4 C3 C2 119.4(2) . . ? C5 C4 C3 120.6(2) . . ? C4 C5 C6 120.87(19) . . ? C1 C6 C5 118.40(19) . . ? C1 C6 C7 120.23(18) . . ? C5 C6 C7 121.36(17) . . ? C6 C7 C8 114.89(16) . . ? C6 C7 C11 113.96(16) . . ? C8 C7 C11 100.64(15) . . ? C9 C8 C12 123.79(18) . . ? C9 C8 C7 113.00(17) . . ? C12 C8 C7 122.93(17) . . ? N2 C9 C8 129.56(18) . . ? N2 C9 C10 121.11(17) . . ? C8 C9 C10 109.13(16) . . ? C14 C10 C9 115.93(15) . . ? C14 C10 C13 109.15(15) . . ? C9 C10 C13 106.67(15) . . ? C14 C10 C11 111.67(15) . . ? C9 C10 C11 102.56(15) . . ? C13 C10 C11 110.60(15) . . ? C10 C11 C7 105.78(15) . . ? N1 C12 C8 179.1(2) . . ? O1 C13 O2 125.04(18) . . ? O1 C13 C10 123.57(18) . . ? O2 C13 C10 111.35(16) . . ? O3 C14 O4 124.99(18) . . ? O3 C14 C10 126.00(17) . . ? O4 C14 C10 109.01(15) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.269 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 939509' ####################################################################### # # 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_3e _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H15 F N2 O4' _chemical_formula_sum 'C16 H15 F N2 O4' _chemical_formula_weight 318.30 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.060(5) _cell_length_b 10.050(5) _cell_length_c 10.085(5) _cell_angle_alpha 96.045(5) _cell_angle_beta 103.961(5) _cell_angle_gamma 99.238(5) _cell_volume 773.6(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1607 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 25.56 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.0052 _exptl_crystal_size_mid 0.0031 _exptl_crystal_size_min 0.0016 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.366 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6952 _exptl_absorpt_correction_T_max 0.7453 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5962 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0734 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 26.16 _reflns_number_total 3070 _reflns_number_gt 2071 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0382P)^2^+0.3132P] 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 3070 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0930 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1080 _refine_ls_wR_factor_gt 0.0945 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F -0.0080(2) 0.11009(15) 0.92468(16) 0.0435(4) Uani 1 1 d . . . O1 O 0.92961(19) 0.26613(14) 0.44680(15) 0.0189(4) Uani 1 1 d . . . O2 O 0.8048(2) 0.08284(15) 0.52188(16) 0.0255(4) Uani 1 1 d . . . O3 O 0.5365(2) 0.28558(14) 0.30799(14) 0.0220(4) Uani 1 1 d . . . O4 O 0.6740(2) 0.49165(15) 0.42595(15) 0.0264(4) Uani 1 1 d . . . N1 N 0.8372(3) 0.3946(2) 1.0372(2) 0.0281(5) Uani 1 1 d . . . N2 N 0.9056(2) 0.48207(17) 0.69208(18) 0.0188(4) Uani 1 1 d . . . H2A H 0.9621 0.5241 0.7731 0.023 Uiso 1 1 calc R . . H2B H 0.9304 0.5098 0.6201 0.023 Uiso 1 1 calc R . . C1 C 0.1393(3) 0.1289(2) 0.8807(2) 0.0240(6) Uani 1 1 d . . . C2 C 0.2348(3) 0.0278(2) 0.8832(2) 0.0245(6) Uani 1 1 d . . . H2 H 0.2027 -0.0518 0.9179 0.029 Uiso 1 1 calc R . . C3 C 0.3811(3) 0.0476(2) 0.8326(2) 0.0196(5) Uani 1 1 d . . . H3 H 0.4470 -0.0203 0.8325 0.024 Uiso 1 1 calc R . . C4 C 0.4307(3) 0.1667(2) 0.7821(2) 0.0146(5) Uani 1 1 d . . . C5 C 0.3318(3) 0.2675(2) 0.7863(2) 0.0186(5) Uani 1 1 d . . . H5 H 0.3653 0.3490 0.7553 0.022 Uiso 1 1 calc R . . C6 C 0.1857(3) 0.2498(2) 0.8351(2) 0.0224(5) Uani 1 1 d . . . H6 H 0.1202 0.3179 0.8372 0.027 Uiso 1 1 calc R . . C7 C 0.5830(3) 0.1842(2) 0.7184(2) 0.0163(5) Uani 1 1 d . . . H7 H 0.6389 0.1047 0.7269 0.020 Uiso 1 1 calc R . . C8 C 0.5278(3) 0.2020(2) 0.5645(2) 0.0147(5) Uani 1 1 d . . . H8A H 0.4955 0.1141 0.5058 0.018 Uiso 1 1 calc R . . H8B H 0.4292 0.2478 0.5471 0.018 Uiso 1 1 calc R . . C9 C 0.6869(3) 0.2886(2) 0.5363(2) 0.0127(5) Uani 1 1 d . . . C10 C 0.7786(3) 0.3732(2) 0.6780(2) 0.0142(5) Uani 1 1 d . . . C11 C 0.7194(3) 0.3134(2) 0.7761(2) 0.0153(5) Uani 1 1 d . . . C12 C 0.7855(3) 0.3590(2) 0.9202(2) 0.0182(5) Uani 1 1 d . . . C13 C 0.6345(3) 0.3703(2) 0.4197(2) 0.0146(5) Uani 1 1 d . . . C14 C 0.4759(3) 0.3471(2) 0.1862(2) 0.0281(6) Uani 1 1 d . . . H14A H 0.4054 0.4112 0.2059 0.042 Uiso 1 1 calc R . . H14B H 0.4079 0.2774 0.1118 0.042 Uiso 1 1 calc R . . H14C H 0.5742 0.3935 0.1601 0.042 Uiso 1 1 calc R . . C15 C 0.8121(3) 0.1984(2) 0.5010(2) 0.0158(5) Uani 1 1 d . . . C16 C 1.0595(3) 0.1900(2) 0.4194(2) 0.0237(6) Uani 1 1 d . . . H16A H 1.1188 0.1621 0.5033 0.036 Uiso 1 1 calc R . . H16B H 1.1421 0.2467 0.3848 0.036 Uiso 1 1 calc R . . H16C H 1.0034 0.1110 0.3519 0.036 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 F1 0.0340(10) 0.0539(10) 0.0630(11) 0.0326(9) 0.0344(9) 0.0194(8) O1 0.0160(9) 0.0184(8) 0.0264(9) 0.0069(7) 0.0095(7) 0.0065(7) O2 0.0295(11) 0.0150(9) 0.0375(10) 0.0083(7) 0.0151(8) 0.0080(7) O3 0.0284(10) 0.0190(8) 0.0141(8) 0.0030(7) -0.0029(7) 0.0039(7) O4 0.0381(11) 0.0143(9) 0.0214(9) 0.0060(7) -0.0014(8) 0.0011(8) N1 0.0237(13) 0.0357(12) 0.0197(11) 0.0005(9) 0.0046(9) -0.0053(10) N2 0.0223(12) 0.0187(10) 0.0127(9) 0.0023(8) 0.0039(8) -0.0027(9) C1 0.0178(14) 0.0350(14) 0.0238(13) 0.0118(11) 0.0107(11) 0.0055(11) C2 0.0276(15) 0.0230(13) 0.0272(13) 0.0126(11) 0.0130(12) 0.0026(11) C3 0.0215(14) 0.0188(12) 0.0181(11) 0.0042(10) 0.0042(10) 0.0036(10) C4 0.0145(13) 0.0156(11) 0.0107(10) 0.0014(9) 0.0001(9) -0.0001(9) C5 0.0212(14) 0.0184(12) 0.0163(11) 0.0050(9) 0.0044(10) 0.0032(10) C6 0.0228(14) 0.0260(13) 0.0219(12) 0.0077(10) 0.0067(11) 0.0115(11) C7 0.0158(13) 0.0148(11) 0.0181(11) 0.0051(9) 0.0033(10) 0.0026(10) C8 0.0117(12) 0.0152(11) 0.0154(11) 0.0016(9) 0.0006(9) 0.0021(9) C9 0.0111(12) 0.0122(10) 0.0139(10) 0.0028(9) 0.0014(9) 0.0015(9) C10 0.0135(12) 0.0116(11) 0.0170(11) 0.0014(9) 0.0032(9) 0.0028(9) C11 0.0128(12) 0.0181(11) 0.0146(11) 0.0023(9) 0.0027(10) 0.0037(9) C12 0.0133(13) 0.0199(12) 0.0219(13) 0.0051(10) 0.0072(10) -0.0001(10) C13 0.0114(12) 0.0172(12) 0.0164(11) 0.0013(9) 0.0062(9) 0.0034(9) C14 0.0367(16) 0.0282(14) 0.0144(12) 0.0054(10) -0.0030(11) 0.0057(12) C15 0.0152(13) 0.0168(12) 0.0134(11) 0.0020(9) 0.0004(10) 0.0024(10) C16 0.0179(14) 0.0249(13) 0.0310(13) 0.0013(11) 0.0098(11) 0.0083(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C1 1.357(3) . ? O1 C15 1.334(3) . ? O1 C16 1.452(2) . ? O2 C15 1.197(3) . ? O3 C13 1.331(3) . ? O3 C14 1.448(3) . ? O4 C13 1.201(2) . ? N1 C12 1.150(3) . ? N2 C10 1.342(3) . ? C1 C2 1.369(3) . ? C1 C6 1.372(3) . ? C2 C3 1.389(3) . ? C3 C4 1.388(3) . ? C4 C5 1.390(3) . ? C4 C7 1.511(3) . ? C5 C6 1.376(3) . ? C7 C11 1.519(3) . ? C7 C8 1.545(3) . ? C8 C9 1.534(3) . ? C9 C13 1.520(3) . ? C9 C10 1.531(3) . ? C9 C15 1.538(3) . ? C10 C11 1.352(3) . ? C11 C12 1.419(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 O1 C16 114.42(16) . . ? C13 O3 C14 116.22(17) . . ? F1 C1 C2 119.2(2) . . ? F1 C1 C6 118.0(2) . . ? C2 C1 C6 122.8(2) . . ? C1 C2 C3 118.0(2) . . ? C4 C3 C2 121.3(2) . . ? C3 C4 C5 118.1(2) . . ? C3 C4 C7 121.16(19) . . ? C5 C4 C7 120.69(19) . . ? C6 C5 C4 121.7(2) . . ? C1 C6 C5 118.1(2) . . ? C4 C7 C11 115.61(17) . . ? C4 C7 C8 112.43(18) . . ? C11 C7 C8 100.39(16) . . ? C9 C8 C7 105.88(17) . . ? C13 C9 C10 115.35(17) . . ? C13 C9 C8 111.75(17) . . ? C10 C9 C8 102.45(16) . . ? C13 C9 C15 109.43(16) . . ? C10 C9 C15 106.80(17) . . ? C8 C9 C15 110.78(17) . . ? N2 C10 C11 129.5(2) . . ? N2 C10 C9 121.20(17) . . ? C11 C10 C9 109.06(19) . . ? C10 C11 C12 124.2(2) . . ? C10 C11 C7 113.46(18) . . ? C12 C11 C7 122.17(18) . . ? N1 C12 C11 179.0(2) . . ? O4 C13 O3 124.9(2) . . ? O4 C13 C9 126.1(2) . . ? O3 C13 C9 109.00(17) . . ? O2 C15 O1 125.03(19) . . ? O2 C15 C9 123.56(19) . . ? O1 C15 C9 111.40(17) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.16 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.237 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 939510' ####################################################################### # # 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_3k _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H18 N2 O4' _chemical_formula_sum 'C20 H18 N2 O4' _chemical_formula_weight 350.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.632(5) _cell_length_b 10.273(5) _cell_length_c 11.899(5) _cell_angle_alpha 82.050(5) _cell_angle_beta 84.145(5) _cell_angle_gamma 70.761(5) _cell_volume 870.8(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 610 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 25.13 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.0045 _exptl_crystal_size_mid 0.0031 _exptl_crystal_size_min 0.0018 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.746079 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4557 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0800 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 4.22 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3005 _reflns_number_gt 1917 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0732P)^2^+0.1936P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3005 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1047 _refine_ls_R_factor_gt 0.0630 _refine_ls_wR_factor_ref 0.1696 _refine_ls_wR_factor_gt 0.1389 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O3 O 0.9660(3) 0.4957(2) 0.16735(18) 0.0274(6) Uani 1 1 d . . . C12 C 0.6286(4) 0.4657(3) 0.2431(3) 0.0226(7) Uani 1 1 d . . . H12A H 0.5029 0.4824 0.2766 0.027 Uiso 1 1 calc R . . H12B H 0.6259 0.5315 0.1760 0.027 Uiso 1 1 calc R . . O1 O 0.6551(4) 0.5703(2) 0.5121(2) 0.0392(7) Uani 1 1 d . . . O2 O 0.5707(3) 0.7067(2) 0.35033(19) 0.0347(6) Uani 1 1 d . . . C13 C 0.7570(4) 0.4800(3) 0.3293(3) 0.0220(7) Uani 1 1 d . . . O4 O 1.0068(3) 0.5759(3) 0.3248(2) 0.0390(7) Uani 1 1 d . . . C3 C 0.2923(4) 0.1640(3) 0.1079(3) 0.0235(7) Uani 1 1 d . . . C14 C 0.8335(4) 0.3310(3) 0.3862(3) 0.0213(7) Uani 1 1 d . . . C11 C 0.7114(4) 0.3157(3) 0.2123(3) 0.0215(7) Uani 1 1 d . . . H11 H 0.8077 0.3123 0.1506 0.026 Uiso 1 1 calc R . . N2 N 0.9246(4) 0.3032(3) 0.4810(2) 0.0281(7) Uani 1 1 d . . . H2A H 0.9745 0.2186 0.5090 0.034 Uiso 1 1 calc R . . H2B H 0.9334 0.3699 0.5141 0.034 Uiso 1 1 calc R . . C2 C 0.2997(4) 0.1824(3) 0.2232(3) 0.0238(7) Uani 1 1 d . . . H2 H 0.2125 0.1625 0.2773 0.029 Uiso 1 1 calc R . . C8 C 0.4280(4) 0.1939(3) 0.0268(3) 0.0224(7) Uani 1 1 d . . . N1 N 0.9100(4) -0.0217(3) 0.3756(3) 0.0349(8) Uani 1 1 d . . . C18 C 0.4825(6) 0.8254(3) 0.4125(3) 0.0396(10) Uani 1 1 d . . . H18A H 0.3968 0.8034 0.4708 0.059 Uiso 1 1 calc R . . H18B H 0.4166 0.9029 0.3613 0.059 Uiso 1 1 calc R . . H18C H 0.5754 0.8487 0.4465 0.059 Uiso 1 1 calc R . . C10 C 0.5681(4) 0.2594(3) 0.1759(3) 0.0189(7) Uani 1 1 d . . . C15 C 0.8033(4) 0.2426(3) 0.3212(3) 0.0211(7) Uani 1 1 d . . . C1 C 0.4328(4) 0.2289(3) 0.2559(3) 0.0235(7) Uani 1 1 d . . . H1 H 0.4345 0.2407 0.3318 0.028 Uiso 1 1 calc R . . C4 C 0.1562(4) 0.1175(3) 0.0707(3) 0.0256(8) Uani 1 1 d . . . H4 H 0.0688 0.0953 0.1233 0.031 Uiso 1 1 calc R . . C17 C 0.6572(4) 0.5871(3) 0.4102(3) 0.0238(7) Uani 1 1 d . . . C6 C 0.2828(5) 0.1358(3) -0.1223(3) 0.0271(8) Uani 1 1 d . . . H6 H 0.2769 0.1280 -0.1986 0.032 Uiso 1 1 calc R . . C16 C 0.8628(4) 0.0971(3) 0.3498(3) 0.0243(8) Uani 1 1 d . . . C19 C 0.9230(5) 0.5236(3) 0.2751(3) 0.0242(8) Uani 1 1 d . . . C7 C 0.4192(4) 0.1773(3) -0.0886(3) 0.0231(7) Uani 1 1 d . . . H7 H 0.5083 0.1950 -0.1422 0.028 Uiso 1 1 calc R . . C5 C 0.1503(5) 0.1046(3) -0.0408(3) 0.0274(8) Uani 1 1 d . . . H5 H 0.0581 0.0750 -0.0637 0.033 Uiso 1 1 calc R . . C9 C 0.5642(4) 0.2411(3) 0.0645(3) 0.0211(7) Uani 1 1 d . . . H9 H 0.6537 0.2604 0.0119 0.025 Uiso 1 1 calc R . . C20 C 1.1224(5) 0.5343(3) 0.1117(3) 0.0323(8) Uani 1 1 d . . . H20A H 1.0960 0.6327 0.1097 0.048 Uiso 1 1 calc R . . H20B H 1.1436 0.5093 0.0355 0.048 Uiso 1 1 calc R . . H20C H 1.2314 0.4866 0.1530 0.048 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 O3 0.0287(13) 0.0348(13) 0.0216(12) -0.0048(10) 0.0002(10) -0.0138(10) C12 0.0210(18) 0.0211(16) 0.0251(18) -0.0010(14) -0.0036(14) -0.0061(13) O1 0.0535(17) 0.0354(14) 0.0230(14) -0.0070(11) -0.0007(12) -0.0054(12) O2 0.0510(16) 0.0220(12) 0.0227(13) -0.0034(10) 0.0008(11) -0.0010(11) C13 0.0232(18) 0.0221(17) 0.0219(17) -0.0037(14) -0.0020(14) -0.0082(14) O4 0.0468(17) 0.0523(16) 0.0309(14) -0.0116(12) -0.0006(12) -0.0312(13) C3 0.0260(19) 0.0194(16) 0.0259(18) -0.0014(14) -0.0058(15) -0.0074(14) C14 0.0187(17) 0.0238(17) 0.0215(17) -0.0047(14) 0.0016(14) -0.0069(13) C11 0.0209(18) 0.0240(17) 0.0204(17) -0.0027(14) -0.0010(14) -0.0084(14) N2 0.0402(18) 0.0208(14) 0.0252(16) -0.0010(12) -0.0149(14) -0.0092(13) C2 0.0224(18) 0.0210(16) 0.0253(18) -0.0017(14) 0.0037(14) -0.0050(14) C8 0.0236(18) 0.0160(16) 0.0253(18) -0.0037(14) -0.0036(14) -0.0020(13) N1 0.0424(19) 0.0292(18) 0.0339(18) -0.0025(14) -0.0125(15) -0.0099(14) C18 0.053(3) 0.0183(17) 0.036(2) -0.0084(16) 0.0103(19) 0.0019(16) C10 0.0173(17) 0.0148(15) 0.0219(17) -0.0006(13) -0.0046(13) -0.0012(12) C15 0.0186(17) 0.0188(16) 0.0239(18) -0.0019(13) -0.0037(14) -0.0026(13) C1 0.0263(19) 0.0223(17) 0.0225(18) -0.0014(14) -0.0024(14) -0.0087(14) C4 0.0201(18) 0.0215(17) 0.034(2) -0.0038(15) -0.0011(15) -0.0048(14) C17 0.0257(19) 0.0250(18) 0.0206(18) -0.0013(14) 0.0039(14) -0.0100(14) C6 0.035(2) 0.0239(17) 0.0225(18) -0.0035(14) -0.0073(16) -0.0084(15) C16 0.0257(19) 0.0259(19) 0.0223(18) -0.0041(14) -0.0058(14) -0.0079(14) C19 0.029(2) 0.0223(17) 0.0222(18) 0.0003(14) -0.0066(15) -0.0095(14) C7 0.0270(19) 0.0217(16) 0.0184(17) 0.0016(13) -0.0015(14) -0.0065(14) C5 0.0255(19) 0.0242(17) 0.035(2) -0.0005(15) -0.0099(16) -0.0104(14) C9 0.0213(18) 0.0215(16) 0.0194(17) 0.0008(13) -0.0027(14) -0.0061(13) C20 0.029(2) 0.037(2) 0.032(2) -0.0029(16) 0.0045(16) -0.0138(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C19 1.337(4) . ? O3 C20 1.449(4) . ? C12 C11 1.541(4) . ? C12 C13 1.541(4) . ? O1 C17 1.201(4) . ? O2 C17 1.331(4) . ? O2 C18 1.447(4) . ? C13 C17 1.519(4) . ? C13 C14 1.532(4) . ? C13 C19 1.533(4) . ? O4 C19 1.199(4) . ? C3 C4 1.408(4) . ? C3 C2 1.420(4) . ? C3 C8 1.421(4) . ? C14 N2 1.333(4) . ? C14 C15 1.358(4) . ? C11 C10 1.517(4) . ? C11 C15 1.519(4) . ? C2 C1 1.365(4) . ? C8 C9 1.415(4) . ? C8 C7 1.418(4) . ? N1 C16 1.158(4) . ? C10 C9 1.369(4) . ? C10 C1 1.415(4) . ? C15 C16 1.414(4) . ? C4 C5 1.358(5) . ? C6 C7 1.361(4) . ? C6 C5 1.412(5) . ? 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 O3 C20 115.5(3) . . ? C11 C12 C13 105.8(2) . . ? C17 O2 C18 117.3(3) . . ? C17 C13 C14 114.9(3) . . ? C17 C13 C19 105.2(2) . . ? C14 C13 C19 107.5(2) . . ? C17 C13 C12 113.0(3) . . ? C14 C13 C12 102.3(2) . . ? C19 C13 C12 114.3(3) . . ? C4 C3 C2 122.7(3) . . ? C4 C3 C8 118.8(3) . . ? C2 C3 C8 118.6(3) . . ? N2 C14 C15 129.5(3) . . ? N2 C14 C13 121.0(3) . . ? C15 C14 C13 109.4(3) . . ? C10 C11 C15 115.5(2) . . ? C10 C11 C12 113.4(2) . . ? C15 C11 C12 100.6(2) . . ? C1 C2 C3 121.0(3) . . ? C9 C8 C7 122.8(3) . . ? C9 C8 C3 118.6(3) . . ? C7 C8 C3 118.6(3) . . ? C9 C10 C1 118.9(3) . . ? C9 C10 C11 120.5(3) . . ? C1 C10 C11 120.5(3) . . ? C14 C15 C16 122.8(3) . . ? C14 C15 C11 112.9(3) . . ? C16 C15 C11 124.2(3) . . ? C2 C1 C10 120.9(3) . . ? C5 C4 C3 121.1(3) . . ? O1 C17 O2 123.9(3) . . ? O1 C17 C13 126.8(3) . . ? O2 C17 C13 109.3(3) . . ? C7 C6 C5 119.7(3) . . ? N1 C16 C15 178.5(4) . . ? O4 C19 O3 123.6(3) . . ? O4 C19 C13 123.4(3) . . ? O3 C19 C13 113.0(3) . . ? C6 C7 C8 121.3(3) . . ? C4 C5 C6 120.6(3) . . ? C10 C9 C8 122.0(3) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.300 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 939511'