# 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_a _database_code_depnum_ccdc_archive 'CCDC 838078' #TrackingRef '6605_web_deposit_cif_file_0_HongbingFu_1312508600.COPV.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H20 N2 O2' _chemical_formula_sum 'C26 H20 N2 O2' _chemical_formula_weight 392.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 8.5110(15) _cell_length_b 14.954(3) _cell_length_c 8.4748(15) _cell_angle_alpha 90.00 _cell_angle_beta 104.292(12) _cell_angle_gamma 90.00 _cell_volume 1045.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 425 _cell_measurement_theta_min 3.12 _cell_measurement_theta_max 68.22 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.632 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.6317 _exptl_absorpt_correction_T_max 0.8428 _exptl_absorpt_process_details 'NUMABS by T.Higashi Jun 3, 2003' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54186 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku raxis Rapid IP Area Detector' _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 9978 _diffrn_reflns_av_R_equivalents 0.0558 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 5.36 _diffrn_reflns_theta_max 68.10 _reflns_number_total 1905 _reflns_number_gt 1428 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto Ver 2.30(Rigaku 1998)' _computing_cell_refinement 'Rapid Auto Ver 2.30(Rigaku 1998)' _computing_data_reduction 'Rapid Auto Ver 2.30(Rigaku 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in Siemens SHELXTL (Sheldrick, 1994)' _computing_publication_material 'SHELX97 (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^)+(0.0411P)^2^+0.2286P] 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 SHELXL _refine_ls_extinction_coef 0.040(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1905 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1224 _refine_ls_wR_factor_gt 0.1121 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 0.99013(18) 0.82116(9) 0.07603(17) 0.0706(5) Uani 1 1 d . . . N1 N 1.5308(3) 1.14234(14) -0.9770(2) 0.0870(7) Uani 1 1 d . . . C1 C 1.4729(2) 1.12059(15) -0.8748(3) 0.0646(6) Uani 1 1 d . . . C2 C 1.4002(2) 1.09403(14) -0.7459(2) 0.0541(5) Uani 1 1 d . . . C3 C 1.3589(2) 1.00597(14) -0.7299(2) 0.0544(5) Uani 1 1 d . . . H3A H 1.3782 0.9622 -0.8041 0.065 Uiso 1 1 calc R . . C4 C 1.2896(2) 0.98186(13) -0.6057(2) 0.0528(5) Uani 1 1 d . . . H4A H 1.2609 0.9211 -0.5959 0.063 Uiso 1 1 calc R . . C5 C 1.2605(2) 1.04386(13) -0.4942(2) 0.0493(5) Uani 1 1 d . . . C6 C 1.3041(2) 1.13243(14) -0.5123(2) 0.0605(6) Uani 1 1 d . . . H6A H 1.2864 1.1762 -0.4373 0.073 Uiso 1 1 calc R . . C7 C 1.3721(3) 1.15751(14) -0.6366(2) 0.0631(6) Uani 1 1 d . . . H7A H 1.3999 1.2183 -0.6477 0.076 Uiso 1 1 calc R . . C8 C 1.1872(2) 1.01396(13) -0.3643(2) 0.0536(5) Uani 1 1 d . . . H8A H 1.1616 0.9521 -0.3641 0.064 Uiso 1 1 calc R . . C9 C 1.1520(2) 1.06261(13) -0.2469(2) 0.0524(5) Uani 1 1 d . . . H9A H 1.1783 1.1244 -0.2447 0.063 Uiso 1 1 calc R . . C10 C 1.0767(2) 1.03010(13) -0.1206(2) 0.0474(5) Uani 1 1 d . . . C11 C 1.0706(2) 0.93971(12) -0.0833(2) 0.0502(5) Uani 1 1 d . . . H11A H 1.1194 0.8974 -0.1401 0.060 Uiso 1 1 calc R . . C12 C 0.9961(2) 0.90977(12) 0.0335(2) 0.0499(5) Uani 1 1 d . . . C13 C 1.0723(3) 0.75807(15) 0.0018(3) 0.0907(8) Uani 1 1 d . . . H13A H 1.0591 0.6983 0.0440 0.136 Uiso 1 1 calc R . . H13B H 1.1878 0.7732 0.0262 0.136 Uiso 1 1 calc R . . H13C H 1.0270 0.7589 -0.1163 0.136 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 0.1026(12) 0.0478(9) 0.0764(10) 0.0056(7) 0.0505(9) 0.0056(8) N1 0.1030(16) 0.0919(16) 0.0834(14) 0.0193(12) 0.0560(13) 0.0155(12) C1 0.0669(13) 0.0742(16) 0.0588(13) 0.0079(11) 0.0270(11) 0.0089(11) C2 0.0544(11) 0.0646(14) 0.0470(11) 0.0039(10) 0.0198(9) 0.0036(9) C3 0.0563(11) 0.0637(14) 0.0448(11) -0.0073(9) 0.0157(9) 0.0030(9) C4 0.0569(11) 0.0558(13) 0.0476(11) -0.0046(9) 0.0164(9) -0.0036(9) C5 0.0513(10) 0.0549(12) 0.0433(10) -0.0007(9) 0.0149(8) -0.0010(9) C6 0.0780(14) 0.0554(13) 0.0558(12) -0.0056(10) 0.0312(11) -0.0030(10) C7 0.0786(14) 0.0577(13) 0.0607(13) 0.0034(11) 0.0315(11) -0.0023(10) C8 0.0614(12) 0.0544(12) 0.0480(11) -0.0016(9) 0.0189(9) -0.0059(9) C9 0.0576(11) 0.0552(12) 0.0467(11) 0.0027(9) 0.0175(9) -0.0014(9) C10 0.0518(10) 0.0521(12) 0.0394(10) 0.0010(8) 0.0137(8) 0.0007(8) C11 0.0598(11) 0.0513(12) 0.0425(10) -0.0019(9) 0.0185(9) 0.0033(9) C12 0.0613(12) 0.0438(12) 0.0470(11) 0.0032(9) 0.0179(9) -0.0009(8) C13 0.127(2) 0.0503(14) 0.116(2) -0.0018(14) 0.0697(18) 0.0092(14) _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 C12 1.377(2) . ? O1 C13 1.411(2) . ? N1 C1 1.144(2) . ? C1 C2 1.438(3) . ? C2 C3 1.378(3) . ? C2 C7 1.388(3) . ? C3 C4 1.375(2) . ? C3 H3A 0.9500 . ? C4 C5 1.389(2) . ? C4 H4A 0.9500 . ? C5 C6 1.394(3) . ? C5 C8 1.464(2) . ? C6 C7 1.373(2) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? C8 C9 1.325(2) . ? C8 H8A 0.9500 . ? C9 C10 1.460(2) . ? C9 H9A 0.9500 . ? C10 C11 1.392(2) . ? C10 C12 1.401(2) 3_775 ? C11 C12 1.376(2) . ? C11 H11A 0.9500 . ? C12 C10 1.401(2) 3_775 ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O1 C13 118.18(16) . . ? N1 C1 C2 179.5(2) . . ? C3 C2 C7 119.85(18) . . ? C3 C2 C1 120.43(18) . . ? C7 C2 C1 119.71(19) . . ? C4 C3 C2 119.57(18) . . ? C4 C3 H3A 120.2 . . ? C2 C3 H3A 120.2 . . ? C3 C4 C5 121.85(18) . . ? C3 C4 H4A 119.1 . . ? C5 C4 H4A 119.1 . . ? C4 C5 C6 117.56(17) . . ? C4 C5 C8 119.25(17) . . ? C6 C5 C8 123.19(17) . . ? C7 C6 C5 121.18(19) . . ? C7 C6 H6A 119.4 . . ? C5 C6 H6A 119.4 . . ? C6 C7 C2 119.99(19) . . ? C6 C7 H7A 120.0 . . ? C2 C7 H7A 120.0 . . ? C9 C8 C5 127.92(19) . . ? C9 C8 H8A 116.0 . . ? C5 C8 H8A 116.0 . . ? C8 C9 C10 126.08(19) . . ? C8 C9 H9A 117.0 . . ? C10 C9 H9A 117.0 . . ? C11 C10 C12 117.22(16) . 3_775 ? C11 C10 C9 122.52(17) . . ? C12 C10 C9 120.25(17) 3_775 . ? C12 C11 C10 121.94(17) . . ? C12 C11 H11A 119.0 . . ? C10 C11 H11A 119.0 . . ? C11 C12 O1 123.68(17) . . ? C11 C12 C10 120.84(17) . 3_775 ? O1 C12 C10 115.46(16) . 3_775 ? O1 C13 H13A 109.5 . . ? O1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 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 N1 C1 C2 C3 177(100) . . . . ? N1 C1 C2 C7 -3(29) . . . . ? C7 C2 C3 C4 0.2(3) . . . . ? C1 C2 C3 C4 179.91(17) . . . . ? C2 C3 C4 C5 -0.4(3) . . . . ? C3 C4 C5 C6 0.0(3) . . . . ? C3 C4 C5 C8 -179.71(17) . . . . ? C4 C5 C6 C7 0.5(3) . . . . ? C8 C5 C6 C7 -179.76(18) . . . . ? C5 C6 C7 C2 -0.7(3) . . . . ? C3 C2 C7 C6 0.3(3) . . . . ? C1 C2 C7 C6 -179.38(19) . . . . ? C4 C5 C8 C9 179.28(19) . . . . ? C6 C5 C8 C9 -0.5(3) . . . . ? C5 C8 C9 C10 179.15(17) . . . . ? C8 C9 C10 C11 17.1(3) . . . . ? C8 C9 C10 C12 -161.62(19) . . . 3_775 ? C12 C10 C11 C12 0.3(3) 3_775 . . . ? C9 C10 C11 C12 -178.51(16) . . . . ? C10 C11 C12 O1 -178.75(17) . . . . ? C10 C11 C12 C10 -0.3(3) . . . 3_775 ? C13 O1 C12 C11 3.4(3) . . . . ? C13 O1 C12 C10 -175.12(19) . . . 3_775 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 68.10 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.148 _refine_diff_density_min -0.120 _refine_diff_density_rms 0.035