# 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_acam _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 N6 O2' _chemical_formula_weight 422.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.5110(5) _cell_length_b 6.6322(6) _cell_length_c 14.0532(15) _cell_angle_alpha 83.397(8) _cell_angle_beta 81.177(8) _cell_angle_gamma 72.154(8) _cell_volume 481.88(8) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1488 _cell_measurement_theta_min 3.2289 _cell_measurement_theta_max 28.8805 _exptl_crystal_description Plate _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 220 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.95769 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'CrysAlisPro, Oxford Diffraction Ltd' _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 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3516 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0530 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 28.94 _reflns_number_total 2155 _reflns_number_gt 1535 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro,Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlisPro,Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlisPro,Oxford Diffraction Ltd' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'OLEX2 (Dolomanov, 2009)' _computing_publication_material 'OLEX2 (Dolomanov, 2009)' _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^+3.6189P] 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 0.070(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2155 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1231 _refine_ls_R_factor_gt 0.0966 _refine_ls_wR_factor_ref 0.2960 _refine_ls_wR_factor_gt 0.2863 _refine_ls_goodness_of_fit_ref 1.234 _refine_ls_restrained_S_all 1.234 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.5781(9) 0.2708(8) 0.2608(4) 0.0475(14) Uani 1 1 d . . . N1 N 0.5911(10) -0.4896(8) 0.0180(4) 0.0343(13) Uani 1 1 d . . . C5 C -0.2747(13) 0.7034(12) 0.4417(5) 0.0450(18) Uani 1 1 d . . . H5 H -0.4337 0.7288 0.4795 0.054 Uiso 1 1 calc R . . N3 N 0.1487(11) 0.3179(9) 0.2769(4) 0.0359(13) Uani 1 1 d . . . N4 N 0.0933(11) 0.8174(9) 0.3827(5) 0.0449(16) Uani 1 1 d . . . C1 C 0.4336(12) 0.0359(9) 0.1832(4) 0.0291(13) Uani 1 1 d . . . C2 C 0.6655(12) -0.1201(9) 0.1798(5) 0.0320(14) Uani 1 1 d . . . H2 H 0.7914 -0.1103 0.2146 0.038 Uiso 1 1 calc R . . C3 C 0.2933(12) -0.1459(9) 0.0724(5) 0.0319(14) Uani 1 1 d . . . H3 H 0.1697 -0.1537 0.0359 0.038 Uiso 1 1 calc R . . C4 C -0.1774(13) 0.5242(11) 0.3899(5) 0.0391(16) Uani 1 1 d . . . H4 H -0.2684 0.4259 0.3934 0.047 Uiso 1 1 calc R . . C6 C 0.0560(11) 0.4939(9) 0.3333(4) 0.0289(13) Uani 1 1 d . . . C7 C 0.3969(12) 0.2173(10) 0.2437(5) 0.0320(14) Uani 1 1 d . . . C8 C 0.5245(11) -0.3051(10) 0.0721(4) 0.0295(13) Uani 1 1 d . . . C9 C 0.1853(12) 0.6450(9) 0.3311(5) 0.0342(14) Uani 1 1 d . . . H9 H 0.3421 0.6260 0.2923 0.041 Uiso 1 1 calc R . . C10 C 0.7136(12) -0.2932(10) 0.1245(5) 0.0346(14) Uani 1 1 d . . . H10 H 0.8701 -0.3992 0.1227 0.042 Uiso 1 1 calc R . . C11 C 0.2472(12) 0.0253(10) 0.1277(5) 0.0335(14) Uani 1 1 d . . . H11 H 0.0925 0.1333 0.1281 0.040 Uiso 1 1 calc R . . C18 C -0.1346(14) 0.8409(12) 0.4365(5) 0.0455(18) Uani 1 1 d . . . H18 H -0.2010 0.9592 0.4725 0.055 Uiso 1 1 calc R . . H12 H 0.059(15) 0.251(12) 0.275(6) 0.05(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.034(3) 0.040(3) 0.073(4) -0.027(3) -0.015(2) -0.006(2) N1 0.033(3) 0.029(3) 0.043(3) -0.014(2) -0.004(2) -0.008(2) C5 0.032(3) 0.049(4) 0.052(4) -0.017(3) 0.000(3) -0.007(3) N3 0.035(3) 0.034(3) 0.044(3) -0.016(2) 0.002(2) -0.017(2) N4 0.039(3) 0.039(3) 0.061(4) -0.023(3) -0.003(3) -0.012(3) C1 0.032(3) 0.027(3) 0.031(3) -0.004(2) -0.002(2) -0.012(2) C2 0.032(3) 0.027(3) 0.040(3) -0.008(3) -0.008(3) -0.009(2) C3 0.032(3) 0.030(3) 0.037(3) -0.011(3) -0.007(3) -0.008(3) C4 0.035(3) 0.046(4) 0.041(4) -0.012(3) -0.001(3) -0.018(3) C6 0.031(3) 0.028(3) 0.028(3) -0.009(2) -0.006(2) -0.006(2) C7 0.037(3) 0.025(3) 0.035(3) -0.008(2) -0.007(3) -0.009(2) C8 0.031(3) 0.031(3) 0.029(3) -0.011(2) 0.000(2) -0.011(2) C9 0.031(3) 0.025(3) 0.046(4) -0.009(3) 0.000(3) -0.009(2) C10 0.030(3) 0.032(3) 0.043(4) -0.011(3) -0.005(3) -0.007(3) C11 0.028(3) 0.031(3) 0.039(3) -0.011(3) -0.007(3) -0.003(2) C18 0.041(4) 0.042(4) 0.052(4) -0.026(3) -0.004(3) -0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.221(7) . ? N1 N1 1.242(10) 2_645 ? N1 C8 1.436(7) . ? C5 C18 1.353(10) . ? C5 C4 1.385(9) . ? C5 H5 0.9300 . ? N3 C7 1.360(8) . ? N3 C6 1.406(8) . ? N3 H12 0.76(8) . ? N4 C18 1.338(9) . ? N4 C9 1.346(8) . ? C1 C2 1.374(8) . ? C1 C11 1.403(8) . ? C1 C7 1.498(8) . ? C2 C10 1.395(8) . ? C2 H2 0.9300 . ? C3 C8 1.383(8) . ? C3 C11 1.387(8) . ? C3 H3 0.9300 . ? C4 C6 1.375(9) . ? C4 H4 0.9300 . ? C6 C9 1.392(8) . ? C8 C10 1.390(8) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C18 H18 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 N1 C8 113.8(6) 2_645 . ? C18 C5 C4 118.9(7) . . ? C18 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C7 N3 C6 127.9(6) . . ? C7 N3 H12 112(6) . . ? C6 N3 H12 118(6) . . ? C18 N4 C9 116.8(6) . . ? C2 C1 C11 119.7(5) . . ? C2 C1 C7 117.4(5) . . ? C11 C1 C7 122.8(5) . . ? C1 C2 C10 120.6(6) . . ? C1 C2 H2 119.7 . . ? C10 C2 H2 119.7 . . ? C8 C3 C11 119.4(6) . . ? C8 C3 H3 120.3 . . ? C11 C3 H3 120.3 . . ? C6 C4 C5 119.0(6) . . ? C6 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C4 C6 C9 118.3(5) . . ? C4 C6 N3 119.0(6) . . ? C9 C6 N3 122.6(6) . . ? O1 C7 N3 123.0(6) . . ? O1 C7 C1 121.9(6) . . ? N3 C7 C1 115.2(5) . . ? C3 C8 C10 121.0(5) . . ? C3 C8 N1 124.0(5) . . ? C10 C8 N1 115.1(5) . . ? N4 C9 C6 122.9(6) . . ? N4 C9 H9 118.6 . . ? C6 C9 H9 118.6 . . ? C8 C10 C2 119.1(6) . . ? C8 C10 H10 120.4 . . ? C2 C10 H10 120.4 . . ? C3 C11 C1 120.1(6) . . ? C3 C11 H11 119.9 . . ? C1 C11 H11 119.9 . . ? N4 C18 C5 124.1(6) . . ? N4 C18 H18 117.9 . . ? C5 C18 H18 117.9 . . ? 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 C11 C1 C2 C10 -2.4(10) . . . . ? C7 C1 C2 C10 -179.7(6) . . . . ? C18 C5 C4 C6 -1.3(11) . . . . ? C5 C4 C6 C9 0.4(10) . . . . ? C5 C4 C6 N3 -176.7(6) . . . . ? C7 N3 C6 C4 -155.2(7) . . . . ? C7 N3 C6 C9 27.8(10) . . . . ? C6 N3 C7 O1 0.4(11) . . . . ? C6 N3 C7 C1 -178.8(6) . . . . ? C2 C1 C7 O1 26.1(9) . . . . ? C11 C1 C7 O1 -151.2(7) . . . . ? C2 C1 C7 N3 -154.7(6) . . . . ? C11 C1 C7 N3 28.1(9) . . . . ? C11 C3 C8 C10 -1.6(10) . . . . ? C11 C3 C8 N1 179.6(6) . . . . ? N1 N1 C8 C3 -9.8(11) 2_645 . . . ? N1 N1 C8 C10 171.3(7) 2_645 . . . ? C18 N4 C9 C6 -1.0(10) . . . . ? C4 C6 C9 N4 0.8(10) . . . . ? N3 C6 C9 N4 177.8(7) . . . . ? C3 C8 C10 C2 1.5(10) . . . . ? N1 C8 C10 C2 -179.6(6) . . . . ? C1 C2 C10 C8 0.5(10) . . . . ? C8 C3 C11 C1 -0.3(10) . . . . ? C2 C1 C11 C3 2.3(9) . . . . ? C7 C1 C11 C3 179.5(6) . . . . ? C9 N4 C18 C5 0.0(12) . . . . ? C4 C5 C18 N4 1.1(12) . . . . ? _diffrn_measured_fraction_theta_max 0.844 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.368 _refine_diff_density_min -0.325 _refine_diff_density_rms 0.095 _database_code_depnum_ccdc_archive 'CCDC 927917' ####################################################################### # # 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_am-4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H24 N4 O4' _chemical_formula_weight 480.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 4.8327(12) _cell_length_b 14.850(3) _cell_length_c 17.252(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.434(18) _cell_angle_gamma 90.00 _cell_volume 1213.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 765 _cell_measurement_theta_min 3.1230 _cell_measurement_theta_max 28.8805 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.37 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.25887 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'CrysAlisPro, Agilent Technologies' _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 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5625 _diffrn_reflns_av_R_equivalents 0.0636 _diffrn_reflns_av_sigmaI/netI 0.1499 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.65 _diffrn_reflns_theta_max 28.96 _reflns_number_total 2772 _reflns_number_gt 1100 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro,Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlisPro,Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlisPro,Oxford Diffraction Ltd' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'OLEX2 (Dolomanov, 2009)' _computing_publication_material 'OLEX2 (Dolomanov, 2009)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.020(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2772 _refine_ls_number_parameters 165 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.3002 _refine_ls_R_factor_gt 0.1874 _refine_ls_wR_factor_ref 0.5090 _refine_ls_wR_factor_gt 0.4552 _refine_ls_goodness_of_fit_ref 1.331 _refine_ls_restrained_S_all 1.335 _refine_ls_shift/su_max 0.003 _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 -0.1285(14) -0.1467(4) -0.5072(3) 0.078(2) Uani 1 1 d . . . N1 N 0.0413(13) -0.1987(4) -0.3833(3) 0.0487(17) Uani 1 1 d D . . H1 H 0.0459 -0.2626 -0.3430 0.058 Uiso 1 1 d RD . . N2 N -0.9755(14) -0.4777(4) -0.5276(3) 0.0533(17) Uani 1 1 d . . . C1 C -0.7562(16) -0.4108(5) -0.5030(4) 0.0495(19) Uani 1 1 d . . . C2 C -0.691(2) -0.3584(6) -0.5610(5) 0.070(3) Uani 1 1 d . . . H2 H -0.7840 -0.3686 -0.6128 0.084 Uiso 1 1 calc R . . C3 C -0.490(2) -0.2897(6) -0.5466(5) 0.073(3) Uani 1 1 d . . . C4 C -0.3439(15) -0.2774(4) -0.4686(4) 0.0441(18) Uani 1 1 d . . . C5 C -0.4068(17) -0.3335(5) -0.4097(4) 0.058(2) Uani 1 1 d . . . H5 H -0.3101 -0.3258 -0.3579 0.069 Uiso 1 1 calc R . . C6 C -0.612(2) -0.4010(5) -0.4265(5) 0.067(3) Uani 1 1 d . . . H6 H -0.6490 -0.4385 -0.3867 0.080 Uiso 1 1 calc R . . C7 C -0.1339(16) -0.2020(5) -0.4553(4) 0.0491(19) Uani 1 1 d . . . C8 C 0.2448(17) -0.1332(5) -0.3570(4) 0.0492(19) Uani 1 1 d . . . C9 C 0.311(2) -0.0599(5) -0.4001(5) 0.066(2) Uani 1 1 d . . . H9 H 0.2200 -0.0522 -0.4524 0.079 Uiso 1 1 calc R . . C10 C 0.510(2) 0.0010(6) -0.3655(6) 0.078(3) Uani 1 1 d . . . H10 H 0.5497 0.0485 -0.3967 0.094 Uiso 1 1 calc R . . C11 C 0.6522(17) -0.0018(5) -0.2909(4) 0.051(2) Uani 1 1 d . . . C12 C 0.5964(19) -0.0713(6) -0.2501(5) 0.068(3) Uani 1 1 d . . . H12 H 0.6954 -0.0767 -0.1983 0.081 Uiso 1 1 calc R . . C13 C 0.3982(18) -0.1379(5) -0.2789(4) 0.060(2) Uani 1 1 d . . . H13 H 0.3679 -0.1853 -0.2464 0.072 Uiso 1 1 calc R . . O2 O 0.1112(13) -0.3338(4) -0.2495(4) 0.072(2) Uani 1 1 d . . . H2W H 0.1953 -0.3960 -0.2350 0.108 Uiso 1 1 d R . . C14 C -0.070(3) -0.3267(8) -0.1972(6) 0.097(4) Uani 1 1 d . . . H14 H -0.2578 -0.3417 -0.2238 0.146 Uiso 1 1 calc R . . H15 H -0.0663 -0.2662 -0.1776 0.146 Uiso 1 1 calc R . . H16 H -0.0106 -0.3674 -0.1538 0.146 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 0.100(5) 0.064(4) 0.057(3) 0.017(3) -0.013(3) -0.030(3) N1 0.059(4) 0.037(3) 0.045(3) -0.005(2) -0.003(3) -0.011(3) N2 0.056(4) 0.054(4) 0.047(4) 0.002(3) 0.004(3) 0.002(3) C1 0.052(5) 0.046(4) 0.052(4) -0.008(3) 0.013(4) -0.005(4) C2 0.082(6) 0.077(6) 0.045(5) 0.000(4) -0.001(5) -0.022(5) C3 0.075(6) 0.081(6) 0.058(5) -0.006(4) 0.000(5) -0.025(5) C4 0.044(4) 0.039(4) 0.047(4) -0.007(3) 0.004(3) 0.004(3) C5 0.069(5) 0.063(5) 0.039(4) 0.006(4) 0.004(4) -0.022(4) C6 0.086(7) 0.049(5) 0.062(5) 0.003(4) 0.006(5) -0.017(5) C7 0.053(5) 0.044(4) 0.048(4) -0.006(3) 0.005(4) 0.002(4) C8 0.058(5) 0.042(4) 0.047(4) -0.005(3) 0.011(4) 0.002(4) C9 0.085(7) 0.055(5) 0.051(4) 0.001(4) -0.002(5) -0.016(5) C10 0.089(7) 0.055(5) 0.089(7) -0.005(5) 0.015(6) -0.023(5) C11 0.057(5) 0.041(4) 0.048(4) -0.005(3) -0.008(4) -0.007(4) C12 0.076(6) 0.058(5) 0.061(5) -0.020(4) -0.005(5) -0.003(5) C13 0.073(6) 0.055(5) 0.044(4) -0.006(3) -0.007(4) -0.005(4) O2 0.089(5) 0.058(3) 0.073(4) 0.028(3) 0.023(4) 0.012(3) C14 0.118(10) 0.100(8) 0.083(7) 0.014(6) 0.041(7) 0.007(7) _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 C7 1.218(9) . ? N1 C7 1.358(9) . ? N1 C8 1.394(9) . ? N1 H1 1.1734 . ? N2 N2 1.221(11) 3_344 ? N2 C1 1.453(10) . ? C1 C2 1.354(11) . ? C1 C6 1.373(11) . ? C2 C3 1.395(12) . ? C2 H2 0.9300 . ? C3 C4 1.403(11) . ? C4 C5 1.393(10) . ? C4 C7 1.499(10) . ? C5 C6 1.398(11) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C8 C9 1.391(11) . ? C8 C13 1.405(10) . ? C9 C10 1.368(11) . ? C9 H9 0.9300 . ? C10 C11 1.334(11) . ? C10 H10 0.9300 . ? C11 C12 1.306(11) . ? C12 C13 1.398(11) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? O2 C14 1.379(10) . ? O2 H2W 1.0209 . ? C14 H14 0.9600 . ? C14 H15 0.9600 . ? C14 H16 0.9600 . ? 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 C7 N1 C8 126.4(6) . . ? C7 N1 H1 116.6 . . ? C8 N1 H1 116.3 . . ? N2 N2 C1 112.7(8) 3_344 . ? C2 C1 C6 120.0(7) . . ? C2 C1 N2 116.2(7) . . ? C6 C1 N2 123.8(7) . . ? C1 C2 C3 123.0(8) . . ? C1 C2 H2 118.5 . . ? C3 C2 H2 118.5 . . ? C2 C3 C4 117.7(8) . . ? C5 C4 C3 118.7(7) . . ? C5 C4 C7 125.0(7) . . ? C3 C4 C7 116.2(7) . . ? C4 C5 C6 121.7(7) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C1 C6 C5 118.6(8) . . ? C1 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? O1 C7 N1 123.2(7) . . ? O1 C7 C4 120.2(7) . . ? N1 C7 C4 116.6(7) . . ? C9 C8 N1 126.5(7) . . ? C9 C8 C13 114.7(7) . . ? N1 C8 C13 118.8(7) . . ? C10 C9 C8 120.0(8) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C11 C10 C9 125.7(8) . . ? C11 C10 H10 117.2 . . ? C9 C10 H10 117.2 . . ? C12 C11 C10 115.0(7) . . ? C11 C12 C13 124.5(8) . . ? C11 C12 H12 117.7 . . ? C13 C12 H12 117.7 . . ? C12 C13 C8 120.0(8) . . ? C12 C13 H13 120.0 . . ? C8 C13 H13 120.0 . . ? C14 O2 H2W 100.5 . . ? O2 C14 H14 109.5 . . ? O2 C14 H15 109.5 . . ? H14 C14 H15 109.5 . . ? O2 C14 H16 109.5 . . ? H14 C14 H16 109.5 . . ? H15 C14 H16 109.5 . . ? 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 N2 N2 C1 C2 -179.7(9) 3_344 . . . ? N2 N2 C1 C6 2.5(13) 3_344 . . . ? C6 C1 C2 C3 -3.7(14) . . . . ? N2 C1 C2 C3 178.3(8) . . . . ? C1 C2 C3 C4 2.5(15) . . . . ? C2 C3 C4 C5 -0.5(12) . . . . ? C2 C3 C4 C7 -179.0(8) . . . . ? C3 C4 C5 C6 -0.1(12) . . . . ? C7 C4 C5 C6 178.1(7) . . . . ? C2 C1 C6 C5 2.9(13) . . . . ? N2 C1 C6 C5 -179.3(7) . . . . ? C4 C5 C6 C1 -1.0(13) . . . . ? C8 N1 C7 O1 1.4(12) . . . . ? C8 N1 C7 C4 -177.6(6) . . . . ? C5 C4 C7 O1 -166.9(8) . . . . ? C3 C4 C7 O1 11.4(11) . . . . ? C5 C4 C7 N1 12.2(11) . . . . ? C3 C4 C7 N1 -169.5(7) . . . . ? C7 N1 C8 C9 -1.5(12) . . . . ? C7 N1 C8 C13 176.8(7) . . . . ? N1 C8 C9 C10 177.7(7) . . . . ? C13 C8 C9 C10 -0.6(12) . . . . ? C8 C9 C10 C11 -0.9(15) . . . . ? C9 C10 C11 C12 2.1(14) . . . . ? C10 C11 C12 C13 -1.9(13) . . . . ? C11 C12 C13 C8 0.6(13) . . . . ? C9 C8 C13 C12 0.8(11) . . . . ? N1 C8 C13 C12 -177.7(7) . . . . ? _diffrn_measured_fraction_theta_max 0.860 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.583 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.115 _database_code_depnum_ccdc_archive 'CCDC 927918'