# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_z1 _database_code_depnum_ccdc_archive 'CCDC 293679' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 N4 O4' _chemical_formula_weight 350.33 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.4194(13) _cell_length_b 8.2680(17) _cell_length_c 15.213(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.69(3) _cell_angle_gamma 90.00 _cell_volume 806.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5565 _cell_measurement_theta_min 3.39 _cell_measurement_theta_max 27.57 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9634 _exptl_absorpt_correction_T_max 0.9869 _exptl_absorpt_process_details ; Higashi, T. (1995) Progrom for Absorption Correcttion. Rigaku Corporation, Tokyo, Japan. ; _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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method 'Omega scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 7435 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1814 _reflns_number_gt 1256 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction PROCESS-AUTO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0524P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef 0 _refine_ls_number_reflns 1814 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0983 _refine_ls_wR_factor_gt 0.0916 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 H9B H 1.082(3) 0.816(2) 0.3496(14) 0.084(7) Uiso 1 1 d . . . H9C H 1.202(3) 0.923(3) 0.2799(13) 0.079(6) Uiso 1 1 d . . . H9A H 1.314(3) 0.767(2) 0.3226(12) 0.065(5) Uiso 1 1 d . . . H8 H 0.640(2) 0.5942(19) 0.0268(11) 0.061(5) Uiso 1 1 d . . . H7 H 0.956(2) 0.5534(19) 0.1079(10) 0.057(5) Uiso 1 1 d . . . H4 H 0.531(3) 0.992(2) 0.1758(11) 0.063(5) Uiso 1 1 d . . . H5 H 0.849(2) 0.9480(18) 0.2538(11) 0.051(4) Uiso 1 1 d . . . O1 O 0.24157(13) 0.95407(10) 0.06126(6) 0.0396(3) Uani 1 1 d . . . O2 O 1.11740(16) 0.71385(11) 0.23066(7) 0.0524(3) Uani 1 1 d . . . N1 N 0.28330(19) 0.73996(15) -0.02232(9) 0.0506(4) Uani 1 1 d . . . N2 N 0.09735(19) 0.81756(14) -0.05026(9) 0.0491(3) Uani 1 1 d . . . C1 C 0.0818(2) 0.93985(15) 0.00028(9) 0.0380(3) Uani 1 1 d . . . C2 C 0.3620(2) 0.82347(14) 0.04278(9) 0.0381(3) Uani 1 1 d . . . C3 C 0.5554(2) 0.79659(15) 0.09428(9) 0.0375(3) Uani 1 1 d . . . C4 C 0.6182(2) 0.89987(17) 0.16194(10) 0.0472(4) Uani 1 1 d . . . C5 C 0.8042(2) 0.87537(18) 0.20932(11) 0.0491(4) Uani 1 1 d . . . C6 C 0.9306(2) 0.74693(16) 0.18902(9) 0.0394(3) Uani 1 1 d . . . C7 C 0.8675(2) 0.64182(16) 0.12174(10) 0.0452(4) Uani 1 1 d . . . C8 C 0.6830(2) 0.66681(16) 0.07475(10) 0.0435(4) Uani 1 1 d . . . C9 C 1.1842(3) 0.8156(2) 0.30241(14) 0.0633(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 O1 0.0315(5) 0.0435(5) 0.0429(6) 0.0003(4) -0.0066(4) 0.0042(4) O2 0.0387(6) 0.0544(6) 0.0624(7) 0.0086(5) -0.0168(5) 0.0027(4) N1 0.0406(7) 0.0535(7) 0.0561(8) -0.0092(6) -0.0135(6) 0.0091(5) N2 0.0399(7) 0.0534(7) 0.0524(8) -0.0041(6) -0.0140(6) 0.0059(5) C1 0.0294(7) 0.0444(7) 0.0395(7) 0.0053(5) -0.0053(5) -0.0015(5) C2 0.0327(7) 0.0385(6) 0.0426(8) 0.0011(6) -0.0015(6) 0.0028(5) C3 0.0311(7) 0.0402(7) 0.0407(8) 0.0042(5) -0.0038(6) 0.0011(5) C4 0.0410(9) 0.0473(8) 0.0525(9) -0.0081(6) -0.0068(7) 0.0113(6) C5 0.0448(9) 0.0513(8) 0.0498(10) -0.0089(7) -0.0121(7) 0.0039(7) C6 0.0310(7) 0.0428(7) 0.0439(8) 0.0123(6) -0.0054(6) -0.0006(5) C7 0.0399(8) 0.0407(7) 0.0544(9) 0.0020(6) -0.0042(7) 0.0094(6) C8 0.0412(8) 0.0409(7) 0.0475(9) -0.0017(6) -0.0065(6) 0.0045(6) C9 0.0518(11) 0.0700(11) 0.0658(13) 0.0087(9) -0.0239(10) -0.0071(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 C1 1.3552(16) . ? O1 C2 1.3650(15) . ? O2 C6 1.3578(16) . ? O2 C9 1.428(2) . ? N1 C2 1.2908(17) . ? N1 N2 1.4034(16) . ? N2 C1 1.2770(18) . ? C1 C1 1.446(3) 3_575 ? C2 C3 1.4537(18) . ? C3 C4 1.383(2) . ? C3 C8 1.390(2) . ? C4 C5 1.381(2) . ? C5 C6 1.380(2) . ? C6 C7 1.389(2) . ? C7 C8 1.370(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 C1 O1 C2 102.02(10) . . ? C6 O2 C9 117.72(13) . . ? C2 N1 N2 106.54(11) . . ? C1 N2 N1 105.60(11) . . ? N2 C1 O1 113.76(11) . . ? N2 C1 C1 128.18(15) . 3_575 ? O1 C1 C1 118.06(15) . 3_575 ? N1 C2 O1 112.08(11) . . ? N1 C2 C3 128.72(12) . . ? O1 C2 C3 119.19(11) . . ? C4 C3 C8 118.80(13) . . ? C4 C3 C2 121.23(12) . . ? C8 C3 C2 119.97(12) . . ? C5 C4 C3 120.85(13) . . ? C6 C5 C4 119.93(14) . . ? O2 C6 C5 124.48(13) . . ? O2 C6 C7 116.02(12) . . ? C5 C6 C7 119.51(12) . . ? C8 C7 C6 120.36(13) . . ? C7 C8 C3 120.55(14) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.204 _refine_diff_density_min -0.123 _refine_diff_density_rms 0.035 data_z1 _database_code_depnum_ccdc_archive 'CCDC 857686' #TrackingRef '8591_web_deposit_cif_file_0_SongnanQu_1323500282.BOXD4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H26 N4 O4' _chemical_formula_weight 434.49 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 8.0873(16) _cell_length_b 8.1278(16) _cell_length_c 9.3175(19) _cell_angle_alpha 107.15(3) _cell_angle_beta 105.03(3) _cell_angle_gamma 97.99(3) _cell_volume 549.59(19) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description biock _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 230 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9785 _exptl_absorpt_correction_T_max 0.9811 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5423 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2492 _reflns_number_gt 1927 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0854P)^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 0.107(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2492 _refine_ls_number_parameters 198 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.1270 _refine_ls_wR_factor_gt 0.1226 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 0.76326(10) 0.93897(10) 0.91286(9) 0.0350(2) Uani 1 1 d . . . N1 N 0.92541(13) 0.82976(14) 1.07478(13) 0.0427(3) Uani 1 1 d . . . C1 C 0.92583(14) 0.94006(14) 1.00047(13) 0.0337(3) Uani 1 1 d . . . O2 O -0.07005(11) 0.66547(13) 0.65568(11) 0.0465(3) Uani 1 1 d . . . N2 N 0.74809(13) 0.74569(14) 1.03545(13) 0.0429(3) Uani 1 1 d . . . C2 C 0.65857(15) 0.81416(14) 0.94173(13) 0.0330(3) Uani 1 1 d . . . C3 C 0.46909(14) 0.77653(15) 0.86630(13) 0.0326(3) Uani 1 1 d . . . C4 C 0.40040(15) 0.86687(16) 0.76880(15) 0.0373(3) Uani 1 1 d . . . H4 H 0.4768(19) 0.9512(19) 0.7526(17) 0.047(4) Uiso 1 1 d . . . C5 C 0.22104(15) 0.83289(16) 0.69594(14) 0.0387(3) Uani 1 1 d . . . H5 H 0.1791(18) 0.9023(19) 0.6298(16) 0.045(3) Uiso 1 1 d . . . C6 C 0.10828(15) 0.70742(16) 0.72111(14) 0.0364(3) Uani 1 1 d . . . C7 C 0.17598(16) 0.61648(16) 0.82000(15) 0.0396(3) Uani 1 1 d . . . H7 H 0.092(2) 0.534(2) 0.8337(17) 0.056(4) Uiso 1 1 d . . . C8 C 0.35470(16) 0.65116(16) 0.89204(15) 0.0380(3) Uani 1 1 d . . . H8 H 0.3994(18) 0.5826(18) 0.9585(16) 0.044(3) Uiso 1 1 d . . . C9 C -0.14539(16) 0.75265(18) 0.55030(16) 0.0417(3) Uani 1 1 d . . . H9B H -0.0948(17) 0.7301(17) 0.4602(16) 0.042(3) Uiso 1 1 d . . . H9A H -0.1165(18) 0.8785(18) 0.6102(16) 0.043(3) Uiso 1 1 d . . . C10 C -0.34115(15) 0.67658(17) 0.48722(15) 0.0383(3) Uani 1 1 d . . . H10B H -0.3630(18) 0.5482(18) 0.4268(16) 0.045(4) Uiso 1 1 d . . . H10A H -0.3845(18) 0.6907(18) 0.5767(16) 0.049(4) Uiso 1 1 d . . . C11 C -0.43417(17) 0.76962(19) 0.38254(17) 0.0453(3) Uani 1 1 d . . . H11B H -0.3824(19) 0.761(2) 0.2985(19) 0.062(4) Uiso 1 1 d . . . H11A H -0.4065(19) 0.897(2) 0.4449(17) 0.057(4) Uiso 1 1 d . . . C12 C -0.63137(18) 0.6954(2) 0.31452(19) 0.0546(4) Uani 1 1 d . . . H12C H -0.663(3) 0.573(3) 0.244(2) 0.095(6) Uiso 1 1 d . . . H12B H -0.684(3) 0.698(3) 0.401(2) 0.093(6) Uiso 1 1 d . . . H12A H -0.694(2) 0.760(2) 0.2541(18) 0.061(4) 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 0.0287(4) 0.0374(4) 0.0395(5) 0.0169(3) 0.0082(3) 0.0068(3) N1 0.0316(5) 0.0467(6) 0.0533(6) 0.0253(5) 0.0100(4) 0.0085(5) C1 0.0272(5) 0.0370(6) 0.0360(6) 0.0127(5) 0.0072(4) 0.0100(5) O2 0.0283(4) 0.0549(6) 0.0592(6) 0.0326(5) 0.0076(4) 0.0026(4) N2 0.0341(5) 0.0447(6) 0.0544(6) 0.0267(5) 0.0107(4) 0.0093(5) C2 0.0326(6) 0.0300(5) 0.0372(6) 0.0124(4) 0.0125(4) 0.0063(5) C3 0.0308(6) 0.0310(6) 0.0357(6) 0.0107(5) 0.0111(4) 0.0072(5) C4 0.0325(6) 0.0363(6) 0.0449(7) 0.0187(5) 0.0124(5) 0.0036(5) C5 0.0333(6) 0.0407(6) 0.0453(7) 0.0228(5) 0.0099(5) 0.0069(5) C6 0.0301(5) 0.0367(6) 0.0408(6) 0.0129(5) 0.0107(5) 0.0052(5) C7 0.0349(6) 0.0385(6) 0.0500(7) 0.0217(6) 0.0158(5) 0.0041(5) C8 0.0366(6) 0.0379(6) 0.0444(7) 0.0200(5) 0.0141(5) 0.0096(5) C9 0.0341(6) 0.0457(7) 0.0444(7) 0.0204(6) 0.0078(5) 0.0046(5) C10 0.0315(6) 0.0419(7) 0.0402(7) 0.0158(6) 0.0102(5) 0.0031(5) C11 0.0397(7) 0.0494(8) 0.0473(7) 0.0216(6) 0.0103(5) 0.0079(6) C12 0.0390(7) 0.0685(10) 0.0525(8) 0.0252(8) 0.0052(6) 0.0094(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 C1 1.3531(13) . ? O1 C2 1.3633(14) . ? N1 C1 1.2843(15) . ? N1 N2 1.4018(15) . ? C1 C1 1.440(2) 2_777 ? O2 C6 1.3611(14) . ? O2 C9 1.4344(15) . ? N2 C2 1.2912(15) . ? C2 C3 1.4561(16) . ? C3 C4 1.3849(16) . ? C3 C8 1.3960(17) . ? C4 C5 1.3815(16) . ? C5 C6 1.3857(17) . ? C6 C7 1.3956(17) . ? C7 C8 1.3752(17) . ? C9 C10 1.5051(17) . ? C10 C11 1.5172(16) . ? C11 C12 1.5140(19) . ? 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 C2 102.05(8) . . ? C1 N1 N2 105.61(9) . . ? N1 C1 O1 113.58(10) . . ? N1 C1 C1 128.46(13) . 2_777 ? O1 C1 C1 117.96(12) . 2_777 ? C6 O2 C9 117.91(9) . . ? C2 N2 N1 106.39(10) . . ? N2 C2 O1 112.36(10) . . ? N2 C2 C3 129.60(11) . . ? O1 C2 C3 118.04(10) . . ? C4 C3 C8 119.25(10) . . ? C4 C3 C2 119.92(11) . . ? C8 C3 C2 120.82(10) . . ? C5 C4 C3 120.81(11) . . ? C4 C5 C6 119.65(11) . . ? O2 C6 C5 124.05(11) . . ? O2 C6 C7 115.93(11) . . ? C5 C6 C7 120.02(11) . . ? C8 C7 C6 119.93(11) . . ? C7 C8 C3 120.34(11) . . ? O2 C9 C10 107.66(10) . . ? C9 C10 C11 111.50(10) . . ? C12 C11 C10 113.25(12) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.231 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.053