# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Torsten Linker' 'Werner Fudickar' _publ_contact_author_name 'Torsten Linker' _publ_contact_author_address ; Chemistry University of Potsdam Potsdam 14476 GERMANY ; _publ_contact_author_email LINKER@CHEM.UNI-POTSDAM.DE _publ_requested_journal 'Chemical Communications' _publ_section_title ; Remote Substituent Effects on the Photooxygenation of 9,10-Diarylanthracenes: Strong Evidence for Polar Intermediates ; data_fud7i _database_code_depnum_ccdc_archive 'CCDC 674791' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H22 O2' _chemical_formula_weight 390.46 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 17.4125(9) _cell_length_b 11.1909(5) _cell_length_c 21.1510(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4121.5(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1648 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 25136 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0167 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3630 _reflns_number_gt 2904 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0621P)^2^+0.4461P] 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 0.0087(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3630 _refine_ls_number_parameters 338 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0499 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1060 _refine_ls_wR_factor_gt 0.1005 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 C1 C 0.08639(7) 0.14806(12) 0.20532(6) 0.0345(3) Uani 1 1 d . . . C2 C 0.07667(7) 0.22406(12) 0.15295(6) 0.0355(3) Uani 1 1 d . . . C3 C 0.02748(8) 0.32593(13) 0.15534(7) 0.0415(3) Uani 1 1 d . . . H3 H -0.0006(9) 0.3394(14) 0.1952(8) 0.050 Uiso 1 1 d . . . C4 C 0.01940(9) 0.39939(14) 0.10482(7) 0.0474(4) Uani 1 1 d . . . H4 H -0.0131(9) 0.4703(16) 0.1092(8) 0.057 Uiso 1 1 d . . . C5 C 0.06060(9) 0.37743(15) 0.04864(7) 0.0501(4) Uani 1 1 d . . . H5 H 0.0550(10) 0.4314(16) 0.0120(8) 0.060 Uiso 1 1 d . . . C6 C 0.10846(8) 0.28217(14) 0.04406(7) 0.0449(4) Uani 1 1 d . . . H6 H 0.1375(9) 0.2674(15) 0.0051(8) 0.054 Uiso 1 1 d . . . C7 C 0.11801(7) 0.20086(12) 0.09545(6) 0.0361(3) Uani 1 1 d . . . C8 C 0.16625(7) 0.10106(12) 0.09116(6) 0.0361(3) Uani 1 1 d . . . C9 C 0.17448(7) 0.02325(12) 0.14274(6) 0.0348(3) Uani 1 1 d . . . C10 C 0.22295(8) -0.07983(13) 0.14048(7) 0.0402(3) Uani 1 1 d . . . H10 H 0.2511(9) -0.0965(14) 0.1022(8) 0.048 Uiso 1 1 d . . . C11 C 0.23065(8) -0.15326(14) 0.19100(7) 0.0445(3) Uani 1 1 d . . . H11 H 0.2642(10) -0.2236(15) 0.1887(7) 0.053 Uiso 1 1 d . . . C12 C 0.19043(9) -0.12935(13) 0.24773(7) 0.0438(3) Uani 1 1 d . . . H12 H 0.1971(9) -0.1822(15) 0.2837(8) 0.053 Uiso 1 1 d . . . C13 C 0.14390(8) -0.03321(13) 0.25216(6) 0.0386(3) Uani 1 1 d . . . H13 H 0.1159(9) -0.0171(13) 0.2901(8) 0.046 Uiso 1 1 d . . . C14 C 0.13388(7) 0.04773(12) 0.20048(6) 0.0339(3) Uani 1 1 d . . . C15 C 0.04888(8) 0.17864(12) 0.26680(6) 0.0389(3) Uani 1 1 d . . . C16 C 0.09061(10) 0.23656(15) 0.31378(7) 0.0520(4) Uani 1 1 d . . . H16 H 0.1479(11) 0.2469(17) 0.3069(8) 0.062 Uiso 1 1 d . . . C17 C 0.05616(13) 0.26832(17) 0.37065(8) 0.0665(5) Uani 1 1 d . . . H17 H 0.0887(12) 0.3098(19) 0.4021(10) 0.080 Uiso 1 1 d . . . C18 C -0.01966(12) 0.24199(18) 0.38051(8) 0.0665(5) Uani 1 1 d . . . H18 H -0.0467(12) 0.2661(19) 0.4214(10) 0.080 Uiso 1 1 d . . . C19 C -0.06176(11) 0.18290(16) 0.33555(7) 0.0565(4) Uani 1 1 d . . . H19 H -0.1166(12) 0.1618(17) 0.3408(9) 0.068 Uiso 1 1 d . . . C20 C -0.02776(8) 0.15079(13) 0.27865(6) 0.0435(3) Uani 1 1 d . . . C21 C -0.13737(10) 0.0409(2) 0.24514(10) 0.0622(5) Uani 1 1 d . . . H21A H -0.1777(12) 0.1029(18) 0.2546(9) 0.075 Uiso 1 1 d . . . H21B H -0.1347(11) -0.0125(18) 0.2836(10) 0.075 Uiso 1 1 d . . . H21C H -0.1516(11) -0.0085(18) 0.2042(10) 0.075 Uiso 1 1 d . . . C22 C 0.21033(8) 0.07747(14) 0.03172(6) 0.0427(3) Uani 1 1 d . . . C23 C 0.28322(9) 0.12502(17) 0.02374(8) 0.0552(4) Uani 1 1 d . . . H23 H 0.3056(11) 0.1786(17) 0.0563(9) 0.066 Uiso 1 1 d . . . C24 C 0.32578(12) 0.1010(2) -0.02985(10) 0.0763(6) Uani 1 1 d . . . H24 H 0.3788(14) 0.137(2) -0.0319(11) 0.092 Uiso 1 1 d . . . C25 C 0.29484(14) 0.0279(3) -0.07545(10) 0.0882(8) Uani 1 1 d . . . H25 H 0.3232(14) 0.014(2) -0.1134(13) 0.106 Uiso 1 1 d . . . C26 C 0.22228(14) -0.0190(2) -0.06938(8) 0.0800(6) Uani 1 1 d . . . H26 H 0.1999(13) -0.069(2) -0.0991(12) 0.096 Uiso 1 1 d . . . C27 C 0.17905(10) 0.00680(16) -0.01568(7) 0.0552(4) Uani 1 1 d . . . C28 C 0.06639(17) -0.0896(3) -0.05576(12) 0.0893(7) Uani 1 1 d . . . H27A H 0.0642(14) -0.035(2) -0.0956(13) 0.107 Uiso 1 1 d . . . H27B H 0.0961(15) -0.164(3) -0.0672(12) 0.107 Uiso 1 1 d . . . H27C H 0.0164(16) -0.113(2) -0.0349(12) 0.107 Uiso 1 1 d . . . O1 O -0.06489(6) 0.09277(11) 0.23123(5) 0.0573(3) Uani 1 1 d . . . O2 O 0.10656(7) -0.03344(14) -0.00535(6) 0.0760(4) 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 C1 0.0317(6) 0.0412(7) 0.0306(6) -0.0029(5) -0.0018(5) -0.0031(5) C2 0.0326(6) 0.0418(7) 0.0321(6) -0.0029(5) -0.0047(5) -0.0024(5) C3 0.0414(7) 0.0444(8) 0.0388(7) -0.0036(6) -0.0051(6) 0.0030(6) C4 0.0473(8) 0.0455(8) 0.0496(8) 0.0008(7) -0.0109(7) 0.0056(7) C5 0.0525(9) 0.0540(9) 0.0439(8) 0.0117(7) -0.0099(7) 0.0014(7) C6 0.0448(8) 0.0559(9) 0.0342(7) 0.0045(6) -0.0036(6) -0.0027(7) C7 0.0329(6) 0.0443(8) 0.0311(6) 0.0002(5) -0.0042(5) -0.0042(6) C8 0.0317(6) 0.0466(8) 0.0299(6) -0.0021(5) -0.0009(5) -0.0042(6) C9 0.0294(6) 0.0425(7) 0.0325(7) -0.0028(5) -0.0010(5) -0.0041(5) C10 0.0362(7) 0.0460(8) 0.0384(7) -0.0031(6) 0.0041(6) 0.0008(6) C11 0.0412(8) 0.0433(8) 0.0489(8) -0.0001(6) 0.0014(6) 0.0040(6) C12 0.0470(8) 0.0434(8) 0.0411(7) 0.0063(6) -0.0002(6) 0.0017(6) C13 0.0406(7) 0.0435(8) 0.0316(7) 0.0003(6) 0.0016(5) -0.0023(6) C14 0.0317(6) 0.0397(7) 0.0303(6) -0.0020(5) -0.0013(5) -0.0040(5) C15 0.0445(7) 0.0398(7) 0.0325(7) -0.0006(5) 0.0007(5) 0.0047(6) C16 0.0622(10) 0.0568(9) 0.0369(8) -0.0076(7) -0.0043(7) -0.0003(8) C17 0.0960(14) 0.0648(11) 0.0386(8) -0.0136(8) -0.0051(9) 0.0040(10) C18 0.0900(14) 0.0732(12) 0.0363(8) -0.0033(8) 0.0137(9) 0.0202(10) C19 0.0583(9) 0.0667(11) 0.0443(8) 0.0052(7) 0.0149(7) 0.0149(8) C20 0.0465(8) 0.0487(8) 0.0354(7) 0.0024(6) 0.0025(6) 0.0061(6) C21 0.0447(9) 0.0704(12) 0.0716(11) 0.0080(10) 0.0067(8) -0.0078(8) C22 0.0413(7) 0.0553(8) 0.0315(7) 0.0040(6) 0.0028(6) 0.0050(7) C23 0.0412(8) 0.0737(11) 0.0506(9) 0.0122(8) 0.0081(7) 0.0009(8) C24 0.0556(10) 0.1088(17) 0.0645(12) 0.0251(12) 0.0236(9) 0.0121(11) C25 0.0822(15) 0.136(2) 0.0465(10) 0.0164(12) 0.0277(10) 0.0360(15) C26 0.0938(16) 0.1096(17) 0.0366(9) -0.0115(10) 0.0037(9) 0.0217(13) C27 0.0565(9) 0.0723(11) 0.0369(8) -0.0048(7) 0.0007(7) 0.0048(8) C28 0.1088(19) 0.0912(16) 0.0680(13) -0.0206(12) -0.0286(13) -0.0228(15) O1 0.0446(6) 0.0796(8) 0.0478(6) -0.0060(5) 0.0054(5) -0.0137(6) O2 0.0687(8) 0.1067(11) 0.0528(7) -0.0281(7) -0.0038(6) -0.0261(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C14 1.3983(19) . ? C1 C2 1.4067(18) . ? C1 C15 1.4949(18) . ? C2 C3 1.427(2) . ? C2 C7 1.4369(18) . ? C3 C4 1.356(2) . ? C4 C5 1.410(2) . ? C5 C6 1.357(2) . ? C6 C7 1.4273(19) . ? C7 C8 1.4003(19) . ? C8 C9 1.4032(18) . ? C8 C22 1.4965(18) . ? C9 C10 1.4302(19) . ? C9 C14 1.4373(17) . ? C10 C11 1.355(2) . ? C11 C12 1.415(2) . ? C12 C13 1.350(2) . ? C13 C14 1.4303(19) . ? C15 C16 1.391(2) . ? C15 C20 1.393(2) . ? C16 C17 1.390(2) . ? C17 C18 1.369(3) . ? C18 C19 1.371(3) . ? C19 C20 1.389(2) . ? C20 O1 1.3585(18) . ? C21 O1 1.4200(19) . ? C22 C23 1.387(2) . ? C22 C27 1.388(2) . ? C23 C24 1.381(2) . ? C24 C25 1.375(4) . ? C25 C26 1.374(3) . ? C26 C27 1.393(2) . ? C27 O2 1.358(2) . ? C28 O2 1.422(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 C14 C1 C2 119.93(11) . . ? C14 C1 C15 120.39(11) . . ? C2 C1 C15 119.60(12) . . ? C1 C2 C3 121.82(12) . . ? C1 C2 C7 119.80(12) . . ? C3 C2 C7 118.37(12) . . ? C4 C3 C2 121.26(14) . . ? C3 C4 C5 120.40(14) . . ? C6 C5 C4 120.66(14) . . ? C5 C6 C7 121.20(14) . . ? C8 C7 C6 121.94(12) . . ? C8 C7 C2 119.96(12) . . ? C6 C7 C2 118.10(12) . . ? C7 C8 C9 120.39(11) . . ? C7 C8 C22 120.18(12) . . ? C9 C8 C22 119.42(12) . . ? C8 C9 C10 122.33(11) . . ? C8 C9 C14 119.48(12) . . ? C10 C9 C14 118.19(12) . . ? C11 C10 C9 121.42(13) . . ? C10 C11 C12 120.35(14) . . ? C13 C12 C11 120.44(14) . . ? C12 C13 C14 121.66(13) . . ? C1 C14 C13 121.65(11) . . ? C1 C14 C9 120.40(12) . . ? C13 C14 C9 117.94(12) . . ? C16 C15 C20 118.42(13) . . ? C16 C15 C1 119.99(13) . . ? C20 C15 C1 121.59(12) . . ? C17 C16 C15 120.78(17) . . ? C18 C17 C16 119.54(17) . . ? C17 C18 C19 120.93(15) . . ? C18 C19 C20 119.88(17) . . ? O1 C20 C19 124.11(14) . . ? O1 C20 C15 115.46(12) . . ? C19 C20 C15 120.43(14) . . ? C23 C22 C27 119.32(14) . . ? C23 C22 C8 120.28(14) . . ? C27 C22 C8 120.40(13) . . ? C24 C23 C22 121.11(19) . . ? C25 C24 C23 118.8(2) . . ? C26 C25 C24 121.48(18) . . ? C25 C26 C27 119.6(2) . . ? O2 C27 C22 115.94(13) . . ? O2 C27 C26 124.39(17) . . ? C22 C27 C26 119.67(18) . . ? C20 O1 C21 117.74(13) . . ? C27 O2 C28 118.90(17) . . ? 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 C14 C1 C2 C3 178.62(12) . . . . ? C15 C1 C2 C3 -4.43(18) . . . . ? C14 C1 C2 C7 -2.46(18) . . . . ? C15 C1 C2 C7 174.49(11) . . . . ? C1 C2 C3 C4 179.10(13) . . . . ? C7 C2 C3 C4 0.2(2) . . . . ? C2 C3 C4 C5 -0.9(2) . . . . ? C3 C4 C5 C6 0.5(2) . . . . ? C4 C5 C6 C7 0.6(2) . . . . ? C5 C6 C7 C8 178.98(14) . . . . ? C5 C6 C7 C2 -1.3(2) . . . . ? C1 C2 C7 C8 1.66(18) . . . . ? C3 C2 C7 C8 -179.38(12) . . . . ? C1 C2 C7 C6 -178.05(12) . . . . ? C3 C2 C7 C6 0.91(18) . . . . ? C6 C7 C8 C9 179.75(12) . . . . ? C2 C7 C8 C9 0.06(18) . . . . ? C6 C7 C8 C22 0.60(19) . . . . ? C2 C7 C8 C22 -179.10(12) . . . . ? C7 C8 C9 C10 179.87(12) . . . . ? C22 C8 C9 C10 -0.97(19) . . . . ? C7 C8 C9 C14 -0.95(18) . . . . ? C22 C8 C9 C14 178.21(12) . . . . ? C8 C9 C10 C11 179.40(13) . . . . ? C14 C9 C10 C11 0.21(19) . . . . ? C9 C10 C11 C12 0.0(2) . . . . ? C10 C11 C12 C13 0.1(2) . . . . ? C11 C12 C13 C14 -0.4(2) . . . . ? C2 C1 C14 C13 -178.56(12) . . . . ? C15 C1 C14 C13 4.51(19) . . . . ? C2 C1 C14 C9 1.58(18) . . . . ? C15 C1 C14 C9 -175.35(11) . . . . ? C12 C13 C14 C1 -179.24(13) . . . . ? C12 C13 C14 C9 0.62(19) . . . . ? C8 C9 C14 C1 0.13(18) . . . . ? C10 C9 C14 C1 179.35(12) . . . . ? C8 C9 C14 C13 -179.73(11) . . . . ? C10 C9 C14 C13 -0.52(18) . . . . ? C14 C1 C15 C16 79.56(18) . . . . ? C2 C1 C15 C16 -97.38(16) . . . . ? C14 C1 C15 C20 -100.59(16) . . . . ? C2 C1 C15 C20 82.47(17) . . . . ? C20 C15 C16 C17 -1.4(2) . . . . ? C1 C15 C16 C17 178.41(15) . . . . ? C15 C16 C17 C18 0.1(3) . . . . ? C16 C17 C18 C19 1.1(3) . . . . ? C17 C18 C19 C20 -1.1(3) . . . . ? C18 C19 C20 O1 -179.63(15) . . . . ? C18 C19 C20 C15 -0.2(2) . . . . ? C16 C15 C20 O1 -179.08(14) . . . . ? C1 C15 C20 O1 1.1(2) . . . . ? C16 C15 C20 C19 1.5(2) . . . . ? C1 C15 C20 C19 -178.36(14) . . . . ? C7 C8 C22 C23 89.80(17) . . . . ? C9 C8 C22 C23 -89.37(18) . . . . ? C7 C8 C22 C27 -90.87(18) . . . . ? C9 C8 C22 C27 89.96(17) . . . . ? C27 C22 C23 C24 -1.5(3) . . . . ? C8 C22 C23 C24 177.83(16) . . . . ? C22 C23 C24 C25 -0.4(3) . . . . ? C23 C24 C25 C26 1.5(3) . . . . ? C24 C25 C26 C27 -0.6(3) . . . . ? C23 C22 C27 O2 -177.99(15) . . . . ? C8 C22 C27 O2 2.7(2) . . . . ? C23 C22 C27 C26 2.4(3) . . . . ? C8 C22 C27 C26 -176.92(16) . . . . ? C25 C26 C27 O2 179.1(2) . . . . ? C25 C26 C27 C22 -1.4(3) . . . . ? C19 C20 O1 C21 -13.1(2) . . . . ? C15 C20 O1 C21 167.45(15) . . . . ? C22 C27 O2 C28 169.92(19) . . . . ? C26 C27 O2 C28 -10.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.173 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.034 # Attachment 'Anthracene1g.CIF' data_fud10i _database_code_depnum_ccdc_archive 'CCDC 674792' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H16 N2' _chemical_formula_weight 380.43 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 10.9801(10) _cell_length_b 14.1658(15) _cell_length_c 12.9428(13) _cell_angle_alpha 90.00 _cell_angle_beta 92.150(8) _cell_angle_gamma 90.00 _cell_volume 2011.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.256 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 12604 _diffrn_reflns_av_R_equivalents 0.0489 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3504 _reflns_number_gt 2492 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0553P)^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 0.022(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3504 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0899 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 0.936 _refine_ls_restrained_S_all 0.936 _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 C1 C 0.93022(13) 0.06688(10) 0.38615(11) 0.0413(3) Uani 1 1 d . . . H1 H 1.0113(14) 0.0407(10) 0.3724(12) 0.050 Uiso 1 1 d . . . C2 C 0.91519(13) 0.12880(10) 0.46415(12) 0.0454(4) Uani 1 1 d . . . H2 H 0.9868(14) 0.1495(10) 0.5080(12) 0.054 Uiso 1 1 d . . . C3 C 0.79809(13) 0.16409(10) 0.48437(12) 0.0442(3) Uani 1 1 d . . . H3 H 0.7892(14) 0.2097(11) 0.5402(12) 0.053 Uiso 1 1 d . . . C4 C 0.69922(13) 0.13544(9) 0.42661(11) 0.0402(3) Uani 1 1 d . . . H4 H 0.6172(14) 0.1592(10) 0.4428(11) 0.048 Uiso 1 1 d . . . C5 C 0.60967(12) 0.04018(9) 0.28201(11) 0.0375(3) Uani 1 1 d . . . C6 C 0.52405(13) -0.05641(10) 0.13740(12) 0.0458(4) Uani 1 1 d . . . H6 H 0.4421(15) -0.0355(10) 0.1555(13) 0.055 Uiso 1 1 d . . . C7 C 0.53978(14) -0.11492(11) 0.05643(12) 0.0508(4) Uani 1 1 d . . . H7 H 0.4662(15) -0.1387(11) 0.0151(13) 0.061 Uiso 1 1 d . . . C8 C 0.65855(14) -0.14326(11) 0.03047(12) 0.0491(4) Uani 1 1 d . . . H8 H 0.6710(14) -0.1882(11) -0.0295(13) 0.059 Uiso 1 1 d . . . C9 C 0.75744(14) -0.11363(10) 0.08762(11) 0.0422(3) Uani 1 1 d . . . H9 H 0.8411(14) -0.1332(10) 0.0696(12) 0.051 Uiso 1 1 d . . . C10 C 0.84578(11) -0.02448(8) 0.23734(10) 0.0358(3) Uani 1 1 d . . . C11 C 0.71073(12) 0.07110(8) 0.34276(10) 0.0357(3) Uani 1 1 d . . . C12 C 0.62503(12) -0.02232(9) 0.19966(10) 0.0374(3) Uani 1 1 d . . . C13 C 0.74507(11) -0.05341(9) 0.17506(10) 0.0364(3) Uani 1 1 d . . . C14 C 0.83023(11) 0.03670(8) 0.32092(10) 0.0358(3) Uani 1 1 d . . . C15 C 0.96969(12) -0.06136(9) 0.21487(11) 0.0372(3) Uani 1 1 d . . . C16 C 1.00609(13) -0.15026(9) 0.24959(12) 0.0424(3) Uani 1 1 d . . . H16 H 0.9496(14) -0.1898(11) 0.2910(12) 0.051 Uiso 1 1 d . . . C17 C 1.12020(13) -0.18529(10) 0.22916(12) 0.0469(4) Uani 1 1 d . . . H17 H 1.1423(14) -0.2470(11) 0.2557(12) 0.056 Uiso 1 1 d . . . C18 C 1.19994(14) -0.13296(10) 0.17295(13) 0.0481(4) Uani 1 1 d . . . H18 H 1.2817(15) -0.1576(11) 0.1599(12) 0.058 Uiso 1 1 d . . . C19 C 1.16693(13) -0.04518(10) 0.13729(13) 0.0460(4) Uani 1 1 d . . . H19 H 1.2215(14) -0.0055(11) 0.0959(12) 0.055 Uiso 1 1 d . . . C20 C 1.05199(12) -0.00898(9) 0.15844(11) 0.0385(3) Uani 1 1 d . . . C21 C 1.02014(13) 0.08418(10) 0.12233(12) 0.0448(4) Uani 1 1 d . . . C22 C 0.48488(11) 0.07529(9) 0.30399(11) 0.0379(3) Uani 1 1 d . . . C23 C 0.40697(13) 0.02466(11) 0.36525(13) 0.0482(4) Uani 1 1 d . . . H23 H 0.4356(14) -0.0363(11) 0.3940(12) 0.058 Uiso 1 1 d . . . C24 C 0.29059(14) 0.05789(11) 0.38316(14) 0.0535(4) Uani 1 1 d . . . H24 H 0.2369(15) 0.0205(11) 0.4246(13) 0.064 Uiso 1 1 d . . . C25 C 0.24992(14) 0.14125(11) 0.33970(14) 0.0511(4) Uani 1 1 d . . . H25 H 0.1674(16) 0.1623(11) 0.3503(13) 0.061 Uiso 1 1 d . . . C26 C 0.32506(12) 0.19298(10) 0.27864(12) 0.0448(4) Uani 1 1 d . . . H26 H 0.2995(14) 0.2542(11) 0.2451(12) 0.054 Uiso 1 1 d . . . C27 C 0.44237(12) 0.16034(9) 0.26139(10) 0.0382(3) Uani 1 1 d . . . C28 C 0.51986(13) 0.21597(10) 0.19831(12) 0.0429(3) Uani 1 1 d . . . N1 N 0.99861(13) 0.15897(9) 0.09324(12) 0.0643(4) Uani 1 1 d . . . N2 N 0.57906(13) 0.26171(10) 0.14724(11) 0.0623(4) 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 C1 0.0316(7) 0.0457(7) 0.0466(9) -0.0021(6) 0.0001(6) -0.0009(6) C2 0.0385(8) 0.0503(8) 0.0470(9) -0.0043(7) -0.0036(7) -0.0049(6) C3 0.0429(8) 0.0459(8) 0.0441(8) -0.0072(7) 0.0044(7) -0.0029(6) C4 0.0363(7) 0.0419(7) 0.0427(8) -0.0003(6) 0.0066(6) 0.0009(6) C5 0.0318(7) 0.0382(7) 0.0426(8) 0.0034(6) 0.0031(6) -0.0007(5) C6 0.0340(7) 0.0518(8) 0.0512(9) -0.0009(7) -0.0027(7) -0.0013(6) C7 0.0449(9) 0.0574(9) 0.0494(9) -0.0062(7) -0.0078(8) -0.0031(7) C8 0.0528(9) 0.0528(8) 0.0416(9) -0.0050(7) -0.0008(7) -0.0008(7) C9 0.0417(8) 0.0458(8) 0.0392(8) 0.0003(6) 0.0038(7) 0.0014(6) C10 0.0314(7) 0.0370(7) 0.0393(8) 0.0027(6) 0.0040(6) -0.0002(5) C11 0.0325(7) 0.0357(6) 0.0392(8) 0.0017(5) 0.0039(6) -0.0010(5) C12 0.0327(7) 0.0393(7) 0.0404(8) 0.0030(6) 0.0021(6) -0.0013(5) C13 0.0340(7) 0.0373(7) 0.0380(8) 0.0026(6) 0.0030(6) -0.0009(5) C14 0.0311(7) 0.0364(7) 0.0399(8) 0.0017(6) 0.0028(6) -0.0010(5) C15 0.0327(7) 0.0397(7) 0.0391(8) -0.0033(6) 0.0007(6) 0.0008(5) C16 0.0376(7) 0.0415(7) 0.0483(8) 0.0017(6) 0.0045(7) -0.0001(6) C17 0.0414(8) 0.0416(8) 0.0575(10) -0.0002(7) -0.0011(7) 0.0068(6) C18 0.0343(8) 0.0490(8) 0.0613(10) -0.0056(7) 0.0047(7) 0.0067(6) C19 0.0338(7) 0.0494(8) 0.0553(10) -0.0019(7) 0.0089(7) -0.0005(6) C20 0.0342(7) 0.0392(7) 0.0423(8) -0.0013(6) 0.0035(6) 0.0008(5) C21 0.0404(8) 0.0461(8) 0.0487(9) -0.0003(7) 0.0109(7) 0.0017(6) C22 0.0297(7) 0.0420(7) 0.0420(8) -0.0022(6) 0.0021(6) -0.0017(5) C23 0.0374(8) 0.0490(8) 0.0587(10) 0.0085(7) 0.0081(7) 0.0008(6) C24 0.0383(8) 0.0550(9) 0.0680(11) 0.0064(8) 0.0145(8) -0.0042(7) C25 0.0316(8) 0.0536(9) 0.0688(11) -0.0035(8) 0.0099(7) 0.0016(6) C26 0.0355(8) 0.0431(8) 0.0559(10) -0.0021(7) 0.0035(7) 0.0029(6) C27 0.0339(7) 0.0399(7) 0.0408(8) -0.0038(6) 0.0026(6) -0.0031(5) C28 0.0398(8) 0.0437(7) 0.0454(8) -0.0014(7) 0.0041(7) -0.0019(6) N1 0.0728(10) 0.0510(8) 0.0700(10) 0.0086(7) 0.0163(8) 0.0111(7) N2 0.0615(9) 0.0634(8) 0.0625(9) 0.0074(7) 0.0114(8) -0.0114(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 C1 C2 1.352(2) . ? C1 C14 1.4252(18) . ? C2 C3 1.413(2) . ? C3 C4 1.3569(19) . ? C4 C11 1.4265(19) . ? C5 C12 1.4007(19) . ? C5 C11 1.4056(18) . ? C5 C22 1.4950(18) . ? C6 C7 1.352(2) . ? C6 C12 1.4300(19) . ? C7 C8 1.417(2) . ? C8 C9 1.357(2) . ? C9 C13 1.4277(19) . ? C10 C14 1.4015(18) . ? C10 C13 1.4049(17) . ? C10 C15 1.4961(18) . ? C11 C14 1.4377(18) . ? C12 C13 1.4366(19) . ? C15 C16 1.3908(18) . ? C15 C20 1.3964(19) . ? C16 C17 1.382(2) . ? C17 C18 1.376(2) . ? C18 C19 1.370(2) . ? C19 C20 1.399(2) . ? C20 C21 1.4387(19) . ? C21 N1 1.1460(18) . ? C22 C23 1.388(2) . ? C22 C27 1.3979(18) . ? C23 C24 1.389(2) . ? C24 C25 1.375(2) . ? C25 C26 1.375(2) . ? C26 C27 1.3944(19) . ? C27 C28 1.437(2) . ? C28 N2 1.1452(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 C2 C1 C14 121.60(13) . . ? C1 C2 C3 120.34(13) . . ? C4 C3 C2 120.46(14) . . ? C3 C4 C11 121.23(13) . . ? C12 C5 C11 120.50(12) . . ? C12 C5 C22 119.50(11) . . ? C11 C5 C22 119.99(12) . . ? C7 C6 C12 121.66(14) . . ? C6 C7 C8 120.19(14) . . ? C9 C8 C7 120.52(14) . . ? C8 C9 C13 121.25(14) . . ? C14 C10 C13 120.48(12) . . ? C14 C10 C15 120.27(11) . . ? C13 C10 C15 119.25(12) . . ? C5 C11 C4 122.28(12) . . ? C5 C11 C14 119.44(12) . . ? C4 C11 C14 118.27(12) . . ? C5 C12 C6 121.96(12) . . ? C5 C12 C13 120.01(11) . . ? C6 C12 C13 118.03(12) . . ? C10 C13 C9 122.20(12) . . ? C10 C13 C12 119.49(12) . . ? C9 C13 C12 118.31(12) . . ? C10 C14 C1 121.95(12) . . ? C10 C14 C11 119.99(11) . . ? C1 C14 C11 118.06(12) . . ? C16 C15 C20 117.80(12) . . ? C16 C15 C10 120.38(12) . . ? C20 C15 C10 121.81(11) . . ? C17 C16 C15 120.98(14) . . ? C18 C17 C16 120.47(14) . . ? C19 C18 C17 120.09(14) . . ? C18 C19 C20 119.74(15) . . ? C15 C20 C19 120.92(12) . . ? C15 C20 C21 120.21(12) . . ? C19 C20 C21 118.87(13) . . ? N1 C21 C20 177.84(16) . . ? C23 C22 C27 117.83(13) . . ? C23 C22 C5 121.73(12) . . ? C27 C22 C5 120.44(12) . . ? C22 C23 C24 120.72(14) . . ? C25 C24 C23 120.61(16) . . ? C26 C25 C24 120.00(14) . . ? C25 C26 C27 119.54(14) . . ? C26 C27 C22 121.29(13) . . ? C26 C27 C28 118.65(13) . . ? C22 C27 C28 120.05(12) . . ? N2 C28 C27 178.22(16) . . ? 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 C14 C1 C2 C3 1.3(2) . . . . ? C1 C2 C3 C4 0.8(2) . . . . ? C2 C3 C4 C11 -1.5(2) . . . . ? C12 C6 C7 C8 -0.7(2) . . . . ? C6 C7 C8 C9 1.3(2) . . . . ? C7 C8 C9 C13 0.0(2) . . . . ? C12 C5 C11 C4 179.34(12) . . . . ? C22 C5 C11 C4 0.37(19) . . . . ? C12 C5 C11 C14 -1.11(19) . . . . ? C22 C5 C11 C14 179.92(12) . . . . ? C3 C4 C11 C5 179.82(13) . . . . ? C3 C4 C11 C14 0.3(2) . . . . ? C11 C5 C12 C6 178.94(13) . . . . ? C22 C5 C12 C6 -2.1(2) . . . . ? C11 C5 C12 C13 -1.61(19) . . . . ? C22 C5 C12 C13 177.36(12) . . . . ? C7 C6 C12 C5 178.35(14) . . . . ? C7 C6 C12 C13 -1.1(2) . . . . ? C14 C10 C13 C9 178.31(12) . . . . ? C15 C10 C13 C9 -2.99(19) . . . . ? C14 C10 C13 C12 -2.07(18) . . . . ? C15 C10 C13 C12 176.63(12) . . . . ? C8 C9 C13 C10 177.81(13) . . . . ? C8 C9 C13 C12 -1.8(2) . . . . ? C5 C12 C13 C10 3.22(19) . . . . ? C6 C12 C13 C10 -177.31(12) . . . . ? C5 C12 C13 C9 -177.14(12) . . . . ? C6 C12 C13 C9 2.33(19) . . . . ? C13 C10 C14 C1 179.51(12) . . . . ? C15 C10 C14 C1 0.82(19) . . . . ? C13 C10 C14 C11 -0.65(19) . . . . ? C15 C10 C14 C11 -179.34(12) . . . . ? C2 C1 C14 C10 177.38(13) . . . . ? C2 C1 C14 C11 -2.5(2) . . . . ? C5 C11 C14 C10 2.27(19) . . . . ? C4 C11 C14 C10 -178.16(12) . . . . ? C5 C11 C14 C1 -177.89(12) . . . . ? C4 C11 C14 C1 1.68(18) . . . . ? C14 C10 C15 C16 97.52(15) . . . . ? C13 C10 C15 C16 -81.18(17) . . . . ? C14 C10 C15 C20 -82.91(17) . . . . ? C13 C10 C15 C20 98.39(15) . . . . ? C20 C15 C16 C17 0.3(2) . . . . ? C10 C15 C16 C17 179.84(13) . . . . ? C15 C16 C17 C18 -0.6(2) . . . . ? C16 C17 C18 C19 0.4(2) . . . . ? C17 C18 C19 C20 0.1(2) . . . . ? C16 C15 C20 C19 0.3(2) . . . . ? C10 C15 C20 C19 -179.29(13) . . . . ? C16 C15 C20 C21 -178.78(13) . . . . ? C10 C15 C20 C21 1.64(19) . . . . ? C18 C19 C20 C15 -0.5(2) . . . . ? C18 C19 C20 C21 178.60(14) . . . . ? C15 C20 C21 N1 160(4) . . . . ? C19 C20 C21 N1 -19(4) . . . . ? C12 C5 C22 C23 85.63(17) . . . . ? C11 C5 C22 C23 -95.38(16) . . . . ? C12 C5 C22 C27 -93.30(15) . . . . ? C11 C5 C22 C27 85.68(16) . . . . ? C27 C22 C23 C24 0.1(2) . . . . ? C5 C22 C23 C24 -178.88(14) . . . . ? C22 C23 C24 C25 0.6(2) . . . . ? C23 C24 C25 C26 -0.6(2) . . . . ? C24 C25 C26 C27 -0.1(2) . . . . ? C25 C26 C27 C22 0.8(2) . . . . ? C25 C26 C27 C28 -179.32(13) . . . . ? C23 C22 C27 C26 -0.8(2) . . . . ? C5 C22 C27 C26 178.21(12) . . . . ? C23 C22 C27 C28 179.33(13) . . . . ? C5 C22 C27 C28 -1.69(19) . . . . ? C26 C27 C28 N2 -12(5) . . . . ? C22 C27 C28 N2 168(5) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.123 _refine_diff_density_min -0.122 _refine_diff_density_rms 0.028