# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global #------------------ AUTHOR DETAILS -------------------------------------------# # SUBMISSION DETAILS _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef '- CCDC812527_1a.cif' #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2010-12-02 _audit_creation_method WinGX _publ_contact_author_name 'Dr. Chitoshi Kitamura' _publ_contact_author_address ; Department of Materials Science and Chemistry Graduate School of Engineering University of Hyogo 2167 Shosha, Himeji, Hyogo 671-2280, Japan ; _publ_contact_author_email kitamura@eng.u-hyogo.ac.jp _publ_contact_author_fax ' 0-81-792-67-4885 ' _publ_contact_author_phone ' 0-81-792-67-4890 ' #----------------------------------------------------------------------------# # TITLE AND AUTHOR LIST loop_ _publ_author_name _publ_author_address C.Kitamura ; Department of Materials Science and Chemistry Graduate School of Engineering University of Hyogo 2167 Shosha, Himeji, Hyogo 671-2280, Japan ; A.Takenaka ; Department of Materials Science and Chemistry Graduate School of Engineering University of Hyogo 2167 Shosha, Himeji, Hyogo 671-2280, Japan ; T.Kawase ; Department of Materials Science and Chemistry Graduate School of Engineering University of Hyogo 2167 Shosha, Himeji, Hyogo 671-2280, Japan ; T.Kobayashi ; Department of Physics and Electronics Graduate School of Engineering Osaka Prefecture University 1-1 Gakuencho, Naka-ku, Sakai 599-8531, Japan ; H.Naito ; Department of Physics and Electronics Graduate School of Engineering Osaka Prefecture University 1-1 Gakuencho, Sakai 599-8531, Japan ; #----------------------------------------------------------------------------# _publ_section_exptl_refinement ; ? ; #----------------------------------------------------------------------------# data_meet _database_code_depnum_ccdc_archive 'CCDC 812527' #TrackingRef '- CCDC812527_1a.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; Octamethyl tetracene-1,2,3,4,7,8,9,10-octacarboxylate ; _chemical_formula_moiety 'C34 H28 O16' _chemical_formula_sum 'C34 H28 O16' _chemical_formula_weight 692.56 _chemical_melting_point ? #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.9021(2) _cell_length_b 12.0619(3) _cell_length_c 12.1167(9) _cell_angle_alpha 114.388(8) _cell_angle_beta 95.781(7) _cell_angle_gamma 95.404(7) _cell_volume 772.81(7) _cell_formula_units_Z 1 _cell_measurement_temperature 200 _cell_measurement_reflns_used 2841 _cell_measurement_theta_min 4.055 _cell_measurement_theta_max 68.195 _cell_measurement_wavelength 1.54178 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.027 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_radiation_source 'FR-E rotating anode with Confocal Mirror' _diffrn_ambient_temperature 200 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 10 _diffrn_measurement_method '\f and \w' _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID 191R' _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_unetI/netI 0.0538 _diffrn_reflns_number 9625 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.05 _diffrn_reflns_theta_max 68.19 _diffrn_reflns_theta_full 68.19 _diffrn_measured_fraction_theta_full 0.974 _diffrn_measured_fraction_theta_max 0.974 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _reflns_number_total 2764 _reflns_number_gt 2019 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'RAPID AUTO (Rigaku, 2006)' _computing_cell_refinement 'RAPID AUTO (Rigaku, 2006)' _computing_data_reduction 'RAPID AUTO (Rigaku, 2006)' _computing_structure_solution 'SIR2004 Giacovazzo et al, 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0792P)^2^+0.4457P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2764 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1686 _refine_ls_wR_factor_gt 0.1593 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.254 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.064 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 0.0501(5) 0.1035(2) 0.2315(2) 0.0306(6) Uani 1 1 d . . . C2 C -0.0564(5) 0.2056(2) 0.2656(2) 0.0309(6) Uani 1 1 d . . . C3 C -0.0156(5) 0.2910(2) 0.2124(2) 0.0322(6) Uani 1 1 d . . . C4 C 0.1357(5) 0.2730(2) 0.1310(2) 0.0305(6) Uani 1 1 d . . . C5 C 0.2547(5) 0.1674(2) 0.0933(2) 0.0307(6) Uani 1 1 d . . . C6 C 0.2041(5) 0.0784(2) 0.1425(2) 0.0297(6) Uani 1 1 d . . . C7 C 0.3102(5) -0.0263(2) 0.1038(2) 0.0322(6) Uani 1 1 d . . . H7 H 0.2734 -0.0863 0.1335 0.039 Uiso 1 1 calc R . . C8 C 0.4704(5) -0.0460(2) 0.0220(2) 0.0313(6) Uani 1 1 d . . . C9 C 0.4166(5) 0.1495(2) 0.0144(2) 0.0327(6) Uani 1 1 d . . . H9 H 0.4516 0.2093 -0.0159 0.039 Uiso 1 1 calc R . . C10 C 0.0117(5) 0.0127(3) 0.2867(2) 0.0331(6) Uani 1 1 d . . . C11 C -0.2677(6) -0.1203(3) 0.3177(3) 0.0554(9) Uani 1 1 d . . . H11A H -0.2008 -0.1955 0.2766 0.083 Uiso 1 1 calc R . . H11B H -0.4356 -0.1409 0.3064 0.083 Uiso 1 1 calc R . . H11C H -0.2064 -0.0824 0.4055 0.083 Uiso 1 1 calc R . . C12 C -0.2272(5) 0.2285(2) 0.3529(3) 0.0336(6) Uani 1 1 d . . . C13 C -0.3103(7) 0.2187(4) 0.5347(3) 0.0604(10) Uani 1 1 d . . . H13A H -0.3287 0.3053 0.5787 0.091 Uiso 1 1 calc R . . H13B H -0.252 0.1878 0.5935 0.091 Uiso 1 1 calc R . . H13C H -0.4597 0.1703 0.4893 0.091 Uiso 1 1 calc R . . C14 C -0.1459(5) 0.3990(3) 0.2441(3) 0.0337(7) Uani 1 1 d . . . C15 C -0.2705(6) 0.5580(3) 0.4052(3) 0.0568(9) Uani 1 1 d . . . H15A H -0.2416 0.6192 0.3726 0.085 Uiso 1 1 calc R . . H15B H -0.246 0.5992 0.495 0.085 Uiso 1 1 calc R . . H15C H -0.4297 0.5162 0.3753 0.085 Uiso 1 1 calc R . . C16 C 0.1823(5) 0.3637(3) 0.0768(3) 0.0352(7) Uani 1 1 d . . . C17 C 0.2993(6) 0.5729(3) 0.1232(3) 0.0509(9) Uani 1 1 d . . . H17A H 0.4668 0.5884 0.1278 0.076 Uiso 1 1 calc R . . H17B H 0.2454 0.6488 0.176 0.076 Uiso 1 1 calc R . . H17C H 0.2254 0.5459 0.0383 0.076 Uiso 1 1 calc R . . O1 O 0.1621(4) -0.0131(2) 0.3424(2) 0.0472(6) Uani 1 1 d . . . O2 O -0.2087(4) -0.03461(18) 0.26524(18) 0.0416(5) Uani 1 1 d . . . O3 O -0.4098(4) 0.2608(2) 0.33875(19) 0.0440(5) Uani 1 1 d . . . O4 O -0.1498(4) 0.20803(19) 0.45018(17) 0.0404(5) Uani 1 1 d . . . O5 O -0.2615(4) 0.41883(19) 0.16906(19) 0.0426(5) Uani 1 1 d . . . O6 O -0.1140(4) 0.46861(18) 0.36475(18) 0.0424(5) Uani 1 1 d . . . O7 O 0.1715(4) 0.3350(2) -0.03145(19) 0.0507(6) Uani 1 1 d . . . O8 O 0.2406(3) 0.47781(17) 0.16386(18) 0.0383(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 C1 0.0315(16) 0.0333(14) 0.0277(14) 0.0146(12) 0.0030(11) 0.0021(11) C2 0.0271(16) 0.0364(15) 0.0308(14) 0.0157(12) 0.0059(12) 0.0035(11) C3 0.0332(17) 0.0341(14) 0.0300(14) 0.0144(12) 0.0038(12) 0.0065(12) C4 0.0324(16) 0.0316(14) 0.0301(14) 0.0155(12) 0.0045(12) 0.0055(11) C5 0.0339(17) 0.0327(14) 0.0267(13) 0.0144(12) 0.0033(11) 0.0041(12) C6 0.0312(16) 0.0322(14) 0.0255(13) 0.0126(11) 0.0039(11) 0.0042(11) C7 0.0385(17) 0.0330(14) 0.0298(14) 0.0179(12) 0.0075(12) 0.0038(12) C8 0.0376(17) 0.0302(14) 0.0274(14) 0.0137(11) 0.0041(12) 0.0051(12) C9 0.0409(18) 0.0313(14) 0.0291(14) 0.0159(12) 0.0057(12) 0.0054(12) C10 0.0346(17) 0.0378(15) 0.0298(14) 0.0155(12) 0.0108(12) 0.0072(12) C11 0.060(2) 0.059(2) 0.058(2) 0.0385(18) 0.0119(18) -0.0067(17) C12 0.0346(18) 0.0332(14) 0.0328(15) 0.0132(12) 0.0079(12) 0.0064(12) C13 0.068(3) 0.084(3) 0.055(2) 0.044(2) 0.0356(19) 0.034(2) C14 0.0311(17) 0.0367(15) 0.0362(15) 0.0169(13) 0.0104(13) 0.0066(12) C15 0.054(2) 0.050(2) 0.058(2) 0.0102(17) 0.0144(18) 0.0228(17) C16 0.0359(18) 0.0374(15) 0.0399(16) 0.0207(13) 0.0121(13) 0.0142(13) C17 0.062(2) 0.0402(17) 0.062(2) 0.0309(16) 0.0179(18) 0.0087(16) O1 0.0424(14) 0.0658(15) 0.0548(13) 0.0435(12) 0.0133(11) 0.0166(11) O2 0.0424(13) 0.0476(12) 0.0397(11) 0.0257(10) 0.0058(10) -0.0036(10) O3 0.0336(13) 0.0562(13) 0.0474(13) 0.0244(11) 0.0110(10) 0.0148(10) O4 0.0434(13) 0.0535(12) 0.0345(11) 0.0243(10) 0.0164(9) 0.0185(10) O5 0.0400(13) 0.0509(13) 0.0450(12) 0.0260(10) 0.0084(10) 0.0157(10) O6 0.0429(13) 0.0414(11) 0.0381(11) 0.0102(9) 0.0086(10) 0.0144(9) O7 0.0772(18) 0.0505(13) 0.0382(12) 0.0267(11) 0.0200(11) 0.0256(12) O8 0.0430(13) 0.0345(11) 0.0420(11) 0.0194(9) 0.0113(9) 0.0073(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.363(4) . ? C1 C6 1.436(4) . ? C1 C10 1.512(4) . ? C2 C3 1.438(4) . ? C2 C12 1.496(4) . ? C3 C4 1.361(4) . ? C3 C14 1.506(4) . ? C4 C5 1.442(4) . ? C4 C16 1.509(4) . ? C5 C9 1.388(4) . ? C5 C6 1.449(4) . ? C6 C7 1.387(4) . ? C7 C8 1.403(4) . ? C7 H7 0.95 . ? C8 C9 1.400(4) 2_655 ? C8 C8 1.447(5) 2_655 ? C9 C8 1.400(4) 2_655 ? C9 H9 0.95 . ? C10 O1 1.202(3) . ? C10 O2 1.325(3) . ? C11 O2 1.454(3) . ? C11 H11A 0.98 . ? C11 H11B 0.98 . ? C11 H11C 0.98 . ? C12 O3 1.200(3) . ? C12 O4 1.346(3) . ? C13 O4 1.439(4) . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? C14 O5 1.198(3) . ? C14 O6 1.334(3) . ? C15 O6 1.449(4) . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? C16 O7 1.203(3) . ? C16 O8 1.329(3) . ? C17 O8 1.451(3) . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? 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 C6 121.4(2) . . ? C2 C1 C10 121.3(2) . . ? C6 C1 C10 117.3(2) . . ? C1 C2 C3 120.2(2) . . ? C1 C2 C12 121.6(2) . . ? C3 C2 C12 118.2(2) . . ? C4 C3 C2 120.3(2) . . ? C4 C3 C14 119.8(2) . . ? C2 C3 C14 119.8(2) . . ? C3 C4 C5 121.5(2) . . ? C3 C4 C16 120.5(2) . . ? C5 C4 C16 117.9(2) . . ? C9 C5 C4 122.6(2) . . ? C9 C5 C6 119.5(2) . . ? C4 C5 C6 117.9(2) . . ? C7 C6 C1 122.6(2) . . ? C7 C6 C5 118.8(2) . . ? C1 C6 C5 118.6(2) . . ? C6 C7 C8 121.9(2) . . ? C6 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? C9 C8 C7 122.2(2) 2_655 . ? C9 C8 C8 118.6(3) 2_655 2_655 ? C7 C8 C8 119.2(3) . 2_655 ? C5 C9 C8 121.9(2) . 2_655 ? C5 C9 H9 119 . . ? C8 C9 H9 119 2_655 . ? O1 C10 O2 124.6(3) . . ? O1 C10 C1 124.3(3) . . ? O2 C10 C1 111.1(2) . . ? O2 C11 H11A 109.5 . . ? O2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O3 C12 O4 124.0(3) . . ? O3 C12 C2 124.8(3) . . ? O4 C12 C2 111.2(2) . . ? O4 C13 H13A 109.5 . . ? O4 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O4 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O5 C14 O6 125.1(3) . . ? O5 C14 C3 123.5(3) . . ? O6 C14 C3 111.5(2) . . ? O6 C15 H15A 109.5 . . ? O6 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O6 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O7 C16 O8 124.9(3) . . ? O7 C16 C4 123.9(3) . . ? O8 C16 C4 111.2(2) . . ? O8 C17 H17A 109.5 . . ? O8 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O8 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C10 O2 C11 116.0(2) . . ? C12 O4 C13 115.1(2) . . ? C14 O6 C15 114.7(2) . . ? C16 O8 C17 116.4(2) . . ? 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 C6 C1 C2 C3 0.0(4) . . . . ? C10 C1 C2 C3 179.5(3) . . . . ? C6 C1 C2 C12 176.5(2) . . . . ? C10 C1 C2 C12 -3.9(4) . . . . ? C1 C2 C3 C4 -2.4(4) . . . . ? C12 C2 C3 C4 -179.0(2) . . . . ? C1 C2 C3 C14 175.9(2) . . . . ? C12 C2 C3 C14 -0.7(4) . . . . ? C2 C3 C4 C5 1.6(4) . . . . ? C14 C3 C4 C5 -176.7(2) . . . . ? C2 C3 C4 C16 -178.9(3) . . . . ? C14 C3 C4 C16 2.8(4) . . . . ? C3 C4 C5 C9 -177.4(3) . . . . ? C16 C4 C5 C9 3.1(4) . . . . ? C3 C4 C5 C6 1.5(4) . . . . ? C16 C4 C5 C6 -178.0(3) . . . . ? C2 C1 C6 C7 -178.3(3) . . . . ? C10 C1 C6 C7 2.1(4) . . . . ? C2 C1 C6 C5 3.1(4) . . . . ? C10 C1 C6 C5 -176.5(2) . . . . ? C9 C5 C6 C7 -3.5(4) . . . . ? C4 C5 C6 C7 177.6(2) . . . . ? C9 C5 C6 C1 175.1(2) . . . . ? C4 C5 C6 C1 -3.8(4) . . . . ? C1 C6 C7 C8 -176.3(3) . . . . ? C5 C6 C7 C8 2.2(4) . . . . ? C6 C7 C8 C9 177.9(3) . . . 2_655 ? C6 C7 C8 C8 1.0(5) . . . 2_655 ? C4 C5 C9 C8 -179.6(2) . . . 2_655 ? C6 C5 C9 C8 1.6(4) . . . 2_655 ? C2 C1 C10 O1 -120.6(3) . . . . ? C6 C1 C10 O1 59.0(4) . . . . ? C2 C1 C10 O2 59.6(3) . . . . ? C6 C1 C10 O2 -120.8(3) . . . . ? C1 C2 C12 O3 -134.3(3) . . . . ? C3 C2 C12 O3 42.2(4) . . . . ? C1 C2 C12 O4 45.6(3) . . . . ? C3 C2 C12 O4 -137.8(3) . . . . ? C4 C3 C14 O5 55.0(4) . . . . ? C2 C3 C14 O5 -123.3(3) . . . . ? C4 C3 C14 O6 -124.5(3) . . . . ? C2 C3 C14 O6 57.1(3) . . . . ? C3 C4 C16 O7 -128.4(3) . . . . ? C5 C4 C16 O7 51.1(4) . . . . ? C3 C4 C16 O8 52.8(4) . . . . ? C5 C4 C16 O8 -127.7(3) . . . . ? O1 C10 O2 C11 2.2(4) . . . . ? C1 C10 O2 C11 -178.0(2) . . . . ? O3 C12 O4 C13 4.5(4) . . . . ? C2 C12 O4 C13 -175.5(3) . . . . ? O5 C14 O6 C15 13.3(4) . . . . ? C3 C14 O6 C15 -167.2(3) . . . . ? O7 C16 O8 C17 -1.3(4) . . . . ? C4 C16 O8 C17 177.5(2) . . . . ? _chemical_name_common 'Octamethyl tetracene-1,2,3,4,7,8,9,10-octacarboxylate' # END of CIF # Attachment '- CCDC812528_1b.cif' data_etet _database_code_depnum_ccdc_archive 'CCDC 812528' #TrackingRef '- CCDC812528_1b.cif' _audit_creation_date 2011-01-08 _audit_creation_method WinGX #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; Octaethyl tetracene-1,2,3,4,7,8,9,10-octacarboxylate ; _chemical_formula_moiety 'C42 H44 O16' _chemical_formula_sum 'C42 H44 O16' _chemical_formula_weight 804.77 _chemical_melting_point ? #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 9.8822(7) _cell_length_b 27.2631(5) _cell_length_c 8.2149(6) _cell_angle_alpha 90 _cell_angle_beta 65.161(8) _cell_angle_gamma 90 _cell_volume 2008.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 200 _cell_measurement_reflns_used 8159 _cell_measurement_theta_min 3.24 _cell_measurement_theta_max 68.18 _cell_measurement_wavelength 1.54178 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.863 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 200 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_unetI/netI 0.0205 _diffrn_reflns_number 24742 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 68.23 _diffrn_reflns_theta_full 68.23 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _reflns_number_total 3662 _reflns_number_gt 3277 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'RAPID AUTO (Rigaku, 2006)' _computing_cell_refinement 'RAPID AUTO (Rigaku, 2006)' _computing_data_reduction 'RAPID AUTO (Rigaku, 2006)' _computing_structure_solution 'SIR2004 Giacovazzo et al, 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0868P)^2^+0.5979P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0075(7) _refine_ls_number_reflns 3662 _refine_ls_number_parameters 267 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1533 _refine_ls_wR_factor_gt 0.1498 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.428 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.066 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 0.39971(18) 0.06231(6) 0.7817(2) 0.0426(4) Uani 1 1 d . . . C2 C 0.43570(18) 0.10884(6) 0.7168(2) 0.0432(4) Uani 1 1 d . . . C3 C 0.32293(18) 0.14203(6) 0.7146(2) 0.0423(4) Uani 1 1 d . . . C4 C 0.17788(18) 0.12719(6) 0.7800(2) 0.0413(4) Uani 1 1 d . . . C5 C 0.13395(18) 0.07885(6) 0.8537(2) 0.0417(4) Uani 1 1 d . . . C6 C 0.24711(18) 0.04558(6) 0.8559(2) 0.0422(4) Uani 1 1 d . . . C7 C 0.20517(18) -0.00065(6) 0.9318(2) 0.0455(4) Uani 1 1 d . . . H7 H 0.2794 -0.0222 0.9352 0.055 Uiso 1 1 calc R . . C8 C 0.05612(18) -0.01633(6) 1.0035(2) 0.0440(4) Uani 1 1 d . . . C9 C -0.01336(18) 0.06314(6) 0.9215(2) 0.0450(4) Uani 1 1 d . . . H9 H -0.0872 0.0847 0.917 0.054 Uiso 1 1 calc R . . C10 C 0.52328(18) 0.02944(6) 0.7787(2) 0.0441(4) Uani 1 1 d . . . C11 C 0.6469(2) -0.04666(8) 0.6709(4) 0.0694(6) Uani 1 1 d . . . H11A H 0.7014 -0.0357 0.7416 0.083 Uiso 1 1 calc R . . H11B H 0.7187 -0.0486 0.5433 0.083 Uiso 1 1 calc R . . C12 C 0.5808(3) -0.09491(9) 0.7334(4) 0.0766(7) Uani 1 1 d . . . H12A H 0.5219 -0.094 0.8636 0.115 Uiso 1 1 calc R . . H12B H 0.6601 -0.1194 0.704 0.115 Uiso 1 1 calc R . . H12C H 0.516 -0.1036 0.6746 0.115 Uiso 1 1 calc R . . C13 C 0.5928(2) 0.12752(7) 0.6534(3) 0.0533(5) Uani 1 1 d . . . C14 C 0.8430(2) 0.11580(10) 0.4349(5) 0.0847(8) Uani 1 1 d . . . H14A H 0.8741 0.1283 0.3113 0.102 Uiso 1 1 calc R . . H14B H 0.8601 0.142 0.5076 0.102 Uiso 1 1 calc R . . C15 C 0.9309(3) 0.07277(12) 0.4325(5) 0.0971(10) Uani 1 1 d . . . H15A H 0.9074 0.0626 0.5559 0.146 Uiso 1 1 calc R . . H15B H 1.0372 0.0807 0.3708 0.146 Uiso 1 1 calc R . . H15C H 0.9072 0.046 0.3691 0.146 Uiso 1 1 calc R . . C16 C 0.37324(19) 0.19070(6) 0.6257(3) 0.0475(4) Uani 1 1 d . . . C17 C 0.3189(3) 0.27540(7) 0.6299(4) 0.0669(6) Uani 1 1 d . . . H17A H 0.3745 0.2726 0.4981 0.08 Uiso 1 1 calc R . . H17B H 0.3821 0.2932 0.6771 0.08 Uiso 1 1 calc R . . C18 C 0.1786(3) 0.30213(8) 0.6747(3) 0.0651(6) Uani 1 1 d . . . H18A H 0.1193 0.2853 0.6215 0.098 Uiso 1 1 calc R . . H18B H 0.2006 0.3356 0.6271 0.098 Uiso 1 1 calc R . . H18C H 0.1223 0.3034 0.8053 0.098 Uiso 1 1 calc R . . C19 C 0.06240(19) 0.16036(6) 0.7631(2) 0.0451(4) Uani 1 1 d . . . C20 C -0.1539(2) 0.20792(9) 0.9216(4) 0.0758(7) Uani 1 1 d . . . H20A H -0.1114 0.2404 0.8729 0.091 Uiso 1 1 calc R . . H20B H -0.1993 0.194 0.8448 0.091 Uiso 1 1 calc R . . C21 C -0.2642(4) 0.21304(17) 1.1007(5) 0.1269(14) Uani 1 1 d . . . H21A H -0.3177 0.1819 1.1408 0.19 Uiso 1 1 calc R . . H21B H -0.3348 0.2388 1.1052 0.19 Uiso 1 1 calc R . . H21C H -0.2162 0.2219 1.1795 0.19 Uiso 1 1 calc R . . O1 O 0.60612(16) 0.04069(5) 0.8449(2) 0.0610(4) Uani 1 1 d . . . O2 O 0.52920(14) -0.01164(5) 0.6912(2) 0.0580(4) Uani 1 1 d . . . O3 O 0.62547(18) 0.16004(7) 0.7279(3) 0.0881(6) Uani 1 1 d . . . O4 O 0.68484(13) 0.10291(5) 0.5112(2) 0.0571(4) Uani 1 1 d . . . O5 O 0.48467(19) 0.19558(5) 0.4920(3) 0.0871(6) Uani 1 1 d . . . O6 O 0.28264(15) 0.22661(4) 0.71056(19) 0.0543(4) Uani 1 1 d . . . O7 O 0.06018(17) 0.17007(6) 0.6227(2) 0.0675(4) Uani 1 1 d . . . O8 O -0.03608(14) 0.17533(5) 0.92150(19) 0.0556(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 0.0331(8) 0.0446(9) 0.0499(9) -0.0022(7) -0.0173(7) 0.0017(7) C2 0.0344(8) 0.0430(9) 0.0493(9) -0.0044(7) -0.0150(7) -0.0001(7) C3 0.0383(8) 0.0405(9) 0.0452(9) -0.0034(7) -0.0147(7) 0.0004(7) C4 0.0379(8) 0.0420(9) 0.0432(9) -0.0006(7) -0.0162(7) 0.0023(6) C5 0.0348(8) 0.0433(9) 0.0467(9) 0.0039(7) -0.0169(7) 0.0015(6) C6 0.0328(8) 0.0456(9) 0.0483(9) 0.0029(7) -0.0172(7) 0.0006(7) C7 0.0324(8) 0.0474(9) 0.0583(11) 0.0073(8) -0.0206(8) 0.0037(7) C8 0.0334(8) 0.0462(9) 0.0528(10) 0.0078(7) -0.0184(7) 0.0011(7) C9 0.0342(8) 0.0466(9) 0.0551(10) 0.0074(8) -0.0195(7) 0.0027(7) C10 0.0322(8) 0.0471(9) 0.0513(10) 0.0038(7) -0.0157(7) -0.0011(7) C11 0.0517(12) 0.0597(12) 0.0989(18) -0.0157(11) -0.0336(12) 0.0216(9) C12 0.0897(17) 0.0604(13) 0.0794(15) -0.0089(11) -0.0351(13) 0.0210(12) C13 0.0399(9) 0.0442(10) 0.0741(13) -0.0034(9) -0.0223(9) -0.0027(7) C14 0.0321(10) 0.0763(15) 0.126(2) 0.0046(14) -0.0140(12) -0.0043(10) C15 0.0452(12) 0.106(2) 0.132(3) -0.0159(19) -0.0292(15) 0.0146(13) C16 0.0410(9) 0.0423(9) 0.0552(11) -0.0036(7) -0.0164(8) -0.0023(7) C17 0.0677(13) 0.0414(10) 0.0886(16) 0.0095(10) -0.0300(12) -0.0011(9) C18 0.0758(14) 0.0546(12) 0.0670(13) 0.0026(9) -0.0321(11) 0.0131(10) C19 0.0389(9) 0.0433(9) 0.0531(10) 0.0058(7) -0.0193(8) -0.0018(7) C20 0.0499(12) 0.0680(14) 0.1036(19) 0.0078(13) -0.0263(12) 0.0205(10) C21 0.091(2) 0.164(4) 0.123(3) -0.048(3) -0.043(2) 0.076(2) O1 0.0527(8) 0.0662(9) 0.0774(10) -0.0077(7) -0.0404(7) 0.0085(6) O2 0.0423(7) 0.0509(8) 0.0865(10) -0.0131(7) -0.0325(7) 0.0110(5) O3 0.0545(9) 0.0754(11) 0.1269(16) -0.0339(10) -0.0306(10) -0.0125(8) O4 0.0322(6) 0.0535(8) 0.0747(9) -0.0024(6) -0.0119(6) -0.0014(5) O5 0.0709(10) 0.0490(8) 0.0910(12) 0.0061(8) 0.0157(9) -0.0034(7) O6 0.0516(7) 0.0399(7) 0.0629(8) 0.0021(5) -0.0158(6) 0.0053(5) O7 0.0593(9) 0.0875(11) 0.0631(9) 0.0132(8) -0.0330(7) 0.0059(7) O8 0.0458(7) 0.0558(8) 0.0612(8) 0.0031(6) -0.0184(6) 0.0141(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.364(2) . ? C1 C6 1.443(2) . ? C1 C10 1.507(2) . ? C2 C3 1.441(2) . ? C2 C13 1.504(2) . ? C3 C4 1.364(2) . ? C3 C16 1.495(2) . ? C4 C5 1.439(2) . ? C4 C19 1.507(2) . ? C5 C9 1.390(2) . ? C5 C6 1.446(2) . ? C6 C7 1.390(2) . ? C7 C8 1.404(2) . ? C7 H7 0.95 . ? C8 C9 1.403(2) 3_557 ? C8 C8 1.442(3) 3_557 ? C9 C8 1.403(2) 3_557 ? C9 H9 0.95 . ? C10 O1 1.198(2) . ? C10 O2 1.318(2) . ? C11 O2 1.459(2) . ? C11 C12 1.462(4) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 0.98 . ? C13 O3 1.197(3) . ? C13 O4 1.323(2) . ? C14 C15 1.455(4) . ? C14 O4 1.462(2) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? C16 O5 1.192(2) . ? C16 O6 1.312(2) . ? C17 O6 1.462(2) . ? C17 C18 1.470(3) . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? C19 O7 1.193(2) . ? C19 O8 1.320(2) . ? C20 C21 1.423(4) . ? C20 O8 1.464(2) . ? C20 H20A 0.99 . ? C20 H20B 0.99 . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? 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 C6 120.92(15) . . ? C2 C1 C10 118.06(15) . . ? C6 C1 C10 121.00(15) . . ? C1 C2 C3 120.84(15) . . ? C1 C2 C13 120.80(16) . . ? C3 C2 C13 118.31(16) . . ? C4 C3 C2 119.94(16) . . ? C4 C3 C16 122.31(15) . . ? C2 C3 C16 117.57(15) . . ? C3 C4 C5 121.25(15) . . ? C3 C4 C19 119.80(15) . . ? C5 C4 C19 118.80(14) . . ? C9 C5 C4 122.08(15) . . ? C9 C5 C6 119.13(15) . . ? C4 C5 C6 118.78(15) . . ? C7 C6 C1 122.55(15) . . ? C7 C6 C5 119.21(15) . . ? C1 C6 C5 118.23(15) . . ? C6 C7 C8 121.81(15) . . ? C6 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? C7 C8 C9 122.07(15) . 3_557 ? C7 C8 C8 118.96(19) . 3_557 ? C9 C8 C8 118.95(19) 3_557 3_557 ? C5 C9 C8 121.89(15) . 3_557 ? C5 C9 H9 119.1 . . ? C8 C9 H9 119.1 3_557 . ? O1 C10 O2 125.64(16) . . ? O1 C10 C1 122.97(17) . . ? O2 C10 C1 111.37(14) . . ? O2 C11 C12 109.35(19) . . ? O2 C11 H11A 109.8 . . ? C12 C11 H11A 109.8 . . ? O2 C11 H11B 109.8 . . ? C12 C11 H11B 109.8 . . ? H11A C11 H11B 108.3 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O3 C13 O4 126.47(18) . . ? O3 C13 C2 122.34(18) . . ? O4 C13 C2 111.18(15) . . ? C15 C14 O4 109.7(2) . . ? C15 C14 H14A 109.7 . . ? O4 C14 H14A 109.7 . . ? C15 C14 H14B 109.7 . . ? O4 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O5 C16 O6 124.49(17) . . ? O5 C16 C3 122.54(16) . . ? O6 C16 C3 112.97(15) . . ? O6 C17 C18 108.15(18) . . ? O6 C17 H17A 110.1 . . ? C18 C17 H17A 110.1 . . ? O6 C17 H17B 110.1 . . ? C18 C17 H17B 110.1 . . ? H17A C17 H17B 108.4 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O7 C19 O8 125.39(17) . . ? O7 C19 C4 122.98(17) . . ? O8 C19 C4 111.59(15) . . ? C21 C20 O8 108.9(2) . . ? C21 C20 H20A 109.9 . . ? O8 C20 H20A 109.9 . . ? C21 C20 H20B 109.9 . . ? O8 C20 H20B 109.9 . . ? H20A C20 H20B 108.3 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C10 O2 C11 117.97(15) . . ? C13 O4 C14 118.14(18) . . ? C16 O6 C17 117.09(16) . . ? C19 O8 C20 116.42(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 C6 C1 C2 C3 -2.3(3) . . . . ? C10 C1 C2 C3 179.53(16) . . . . ? C6 C1 C2 C13 175.00(17) . . . . ? C10 C1 C2 C13 -3.2(3) . . . . ? C1 C2 C3 C4 0.8(3) . . . . ? C13 C2 C3 C4 -176.51(17) . . . . ? C1 C2 C3 C16 -174.38(16) . . . . ? C13 C2 C3 C16 8.3(2) . . . . ? C2 C3 C4 C5 0.6(3) . . . . ? C16 C3 C4 C5 175.64(16) . . . . ? C2 C3 C4 C19 -174.78(15) . . . . ? C16 C3 C4 C19 0.2(3) . . . . ? C3 C4 C5 C9 179.78(17) . . . . ? C19 C4 C5 C9 -4.8(3) . . . . ? C3 C4 C5 C6 -0.7(3) . . . . ? C19 C4 C5 C6 174.81(15) . . . . ? C2 C1 C6 C7 -176.52(17) . . . . ? C10 C1 C6 C7 1.6(3) . . . . ? C2 C1 C6 C5 2.2(3) . . . . ? C10 C1 C6 C5 -179.66(16) . . . . ? C9 C5 C6 C7 -2.4(3) . . . . ? C4 C5 C6 C7 178.04(16) . . . . ? C9 C5 C6 C1 178.84(17) . . . . ? C4 C5 C6 C1 -0.7(2) . . . . ? C1 C6 C7 C8 179.94(17) . . . . ? C5 C6 C7 C8 1.2(3) . . . . ? C6 C7 C8 C9 179.26(18) . . . 3_557 ? C6 C7 C8 C8 0.6(3) . . . 3_557 ? C4 C5 C9 C8 -178.72(17) . . . 3_557 ? C6 C5 C9 C8 1.7(3) . . . 3_557 ? C2 C1 C10 O1 54.3(3) . . . . ? C6 C1 C10 O1 -123.9(2) . . . . ? C2 C1 C10 O2 -124.13(18) . . . . ? C6 C1 C10 O2 57.7(2) . . . . ? C1 C2 C13 O3 -114.2(2) . . . . ? C3 C2 C13 O3 63.2(3) . . . . ? C1 C2 C13 O4 64.7(2) . . . . ? C3 C2 C13 O4 -117.93(18) . . . . ? C4 C3 C16 O5 -136.9(2) . . . . ? C2 C3 C16 O5 38.3(3) . . . . ? C4 C3 C16 O6 43.3(2) . . . . ? C2 C3 C16 O6 -141.61(17) . . . . ? C3 C4 C19 O7 67.9(2) . . . . ? C5 C4 C19 O7 -107.7(2) . . . . ? C3 C4 C19 O8 -114.26(18) . . . . ? C5 C4 C19 O8 70.2(2) . . . . ? O1 C10 O2 C11 -0.5(3) . . . . ? C1 C10 O2 C11 177.81(17) . . . . ? C12 C11 O2 C10 127.4(2) . . . . ? O3 C13 O4 C14 0.2(3) . . . . ? C2 C13 O4 C14 -178.65(19) . . . . ? C15 C14 O4 C13 122.6(3) . . . . ? O5 C16 O6 C17 2.7(3) . . . . ? C3 C16 O6 C17 -177.48(17) . . . . ? C18 C17 O6 C16 148.65(19) . . . . ? O7 C19 O8 C20 -2.3(3) . . . . ? C4 C19 O8 C20 179.92(17) . . . . ? C21 C20 O8 C19 169.3(3) . . . . ? _chemical_name_common 'Octaethyl tetracene-1,2,3,4,7,8,9,10-octacarboxylate' # END of CIF # Attachment '- CCDC812529_1c.cif' data_pret _database_code_depnum_ccdc_archive 'CCDC 812529' #TrackingRef '- CCDC812529_1c.cif' _audit_creation_date 2010-08-05 _audit_creation_method WinGX #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; Octapropyl tetracene-1,2,3,4,7,8,9,10-octacarboxylate ; _chemical_formula_moiety 'C50 H60 O16' _chemical_formula_sum 'C50 H60 O16' _chemical_formula_weight 916.98 _chemical_melting_point 428 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.570(2) _cell_length_b 10.081(2) _cell_length_c 13.754(2) _cell_angle_alpha 72.313(4) _cell_angle_beta 73.227(4) _cell_angle_gamma 73.558(4) _cell_volume 1182.3(4) _cell_formula_units_Z 1 _cell_measurement_temperature 173 _cell_measurement_reflns_used 5718 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 27.415 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.13 _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'fine-focus sealed x-ray tube' _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 10 _diffrn_measurement_device_type 'Rigaku R-Axis Rapid' _diffrn_measurement_method '\f and \w' _diffrn_reflns_av_R_equivalents 0.0823 _diffrn_reflns_av_unetI/netI 0.0824 _diffrn_reflns_number 19549 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _reflns_number_total 5390 _reflns_number_gt 2397 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'RAPID-AUTO (Rigaku, 2006)' _computing_cell_refinement 'RAPID-AUTO (Rigaku, 2006)' _computing_data_reduction 'RAPID-AUTO (Rigaku, 2006)' _computing_structure_solution 'SIR2004 (Giacovazzo et al, 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.1284P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5390 _refine_ls_number_parameters 363 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1546 _refine_ls_R_factor_gt 0.0805 _refine_ls_wR_factor_ref 0.2587 _refine_ls_wR_factor_gt 0.2098 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.969 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.297 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.049 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.5570(4) 0.0998(3) 0.6714(2) 0.0584(8) Uani 1 1 d . . . C2 C 0.6370(4) 0.0383(3) 0.7471(3) 0.0596(8) Uani 1 1 d . . . C3 C 0.7095(4) 0.1216(3) 0.7782(3) 0.0614(9) Uani 1 1 d . B . C4 C 0.6995(4) 0.2632(4) 0.7295(3) 0.0616(8) Uani 1 1 d . . . C5 C 0.6198(4) 0.3317(3) 0.6482(2) 0.0574(8) Uani 1 1 d . . . C6 C 0.5479(4) 0.2484(3) 0.6162(2) 0.0584(8) Uani 1 1 d . . . C7 C 0.4751(4) 0.3130(3) 0.5349(2) 0.0592(8) Uani 1 1 d . . . H7 H 0.4301 0.2575 0.513 0.071 Uiso 1 1 calc R . . C8 C 0.4650(4) 0.4585(3) 0.4834(2) 0.0579(8) Uani 1 1 d . . . C9 C 0.6096(4) 0.4756(3) 0.5975(2) 0.0602(8) Uani 1 1 d . . . H9 H 0.6554 0.5307 0.6192 0.072 Uiso 1 1 calc R . . C10 C 0.4821(4) 0.0088(4) 0.6425(2) 0.0588(8) Uani 1 1 d . . . C11 C 0.2471(4) -0.0121(4) 0.6283(3) 0.0696(10) Uani 1 1 d . . . H11A H 0.1994 -0.076 0.6918 0.084 Uiso 0.480(10) 1 calc PR A 1 H11B H 0.3084 -0.0684 0.5771 0.084 Uiso 0.480(10) 1 calc PR A 1 H11C H 0.2479 -0.1064 0.6784 0.084 Uiso 0.520(10) 1 d PR A 2 H11D H 0.2926 -0.0279 0.5573 0.084 Uiso 0.520(10) 1 d PR A 2 C12A C 0.1317(14) 0.1098(13) 0.5817(9) 0.070(3) Uani 0.480(10) 1 d P A 1 H12A H 0.0731 0.1657 0.6337 0.085 Uiso 0.480(10) 1 calc PR A 1 H12B H 0.1818 0.1739 0.5197 0.085 Uiso 0.480(10) 1 calc PR A 1 C13A C 0.0296(10) 0.0471(10) 0.5504(7) 0.088(3) Uani 0.480(10) 1 d P A 1 H13A H -0.0449 0.1244 0.519 0.133 Uiso 0.480(10) 1 calc PR A 1 H13B H -0.0212 -0.0145 0.6125 0.133 Uiso 0.480(10) 1 calc PR A 1 H13C H 0.0887 -0.0089 0.4995 0.133 Uiso 0.480(10) 1 calc PR A 1 C12B C 0.0914(11) 0.0679(12) 0.6324(8) 0.073(3) Uani 0.520(10) 1 d P A 2 H12C H 0.0522 0.0996 0.6985 0.088 Uiso 0.520(10) 1 calc PR A 2 H12D H 0.0296 0.004 0.6325 0.088 Uiso 0.520(10) 1 calc PR A 2 C13B C 0.0776(12) 0.1988(11) 0.5393(7) 0.087(3) Uani 0.520(10) 1 d P A 2 H13D H -0.027 0.25 0.5462 0.131 Uiso 0.520(10) 1 calc PR A 2 H13E H 0.1118 0.1675 0.4739 0.131 Uiso 0.520(10) 1 calc PR A 2 H13F H 0.1391 0.2621 0.5386 0.131 Uiso 0.520(10) 1 calc PR A 2 C14 C 0.6555(5) -0.1193(4) 0.7973(3) 0.0630(9) Uani 1 1 d . . . C15 C 0.5208(5) -0.3034(4) 0.8953(3) 0.0844(12) Uani 1 1 d . . . H15A H 0.4953 -0.3209 0.9725 0.101 Uiso 1 1 calc R . . H15B H 0.62 -0.3639 0.874 0.101 Uiso 1 1 calc R . . C16 C 0.4043(6) -0.3393(5) 0.8587(3) 0.0892(13) Uani 1 1 d . . . H16A H 0.4293 -0.3171 0.7813 0.107 Uiso 1 1 calc R . . H16B H 0.4083 -0.443 0.8846 0.107 Uiso 1 1 calc R . . C17 C 0.2487(5) -0.2609(5) 0.8946(3) 0.0936(13) Uani 1 1 d . . . H17A H 0.1795 -0.2879 0.8673 0.14 Uiso 1 1 calc R . . H17B H 0.2433 -0.1581 0.8688 0.14 Uiso 1 1 calc R . . H17C H 0.2212 -0.2854 0.9713 0.14 Uiso 1 1 calc R . . C18 C 0.7944(6) 0.0588(4) 0.8620(4) 0.0853(13) Uani 1 1 d . . . C19A C 0.7685(14) -0.0949(10) 1.0452(8) 0.080(3) Uani 0.607(11) 1 d P B 3 H19A H 0.7216 -0.0314 1.0937 0.096 Uiso 0.607(11) 1 calc PR B 3 H19B H 0.878 -0.1028 1.0279 0.096 Uiso 0.607(11) 1 calc PR B 3 C20A C 0.7316(16) -0.2449(13) 1.0975(11) 0.086(4) Uani 0.607(11) 1 d P B 3 H20A H 0.7404 -0.2732 1.1714 0.103 Uiso 0.607(11) 1 calc PR B 3 H20B H 0.6271 -0.2405 1.0969 0.103 Uiso 0.607(11) 1 calc PR B 3 C21A C 0.8331(11) -0.3534(7) 1.0425(7) 0.097(3) Uani 0.607(11) 1 d P B 3 H21A H 0.8056 -0.4459 1.0765 0.146 Uiso 0.607(11) 1 calc PR B 3 H21B H 0.9362 -0.3605 1.0453 0.146 Uiso 0.607(11) 1 calc PR B 3 H21C H 0.8247 -0.3255 0.9693 0.146 Uiso 0.607(11) 1 calc PR B 3 C19B C 0.8568(16) -0.1026(15) 1.0021(11) 0.073(4) Uani 0.393(11) 1 d P B 4 H19C H 0.9064 -0.0363 1.0135 0.087 Uiso 0.393(11) 1 calc PR B 4 H19D H 0.9346 -0.1782 0.9738 0.087 Uiso 0.393(11) 1 calc PR B 4 C20B C 0.7604(13) -0.1661(17) 1.1023(10) 0.067(3) Uani 0.393(11) 1 d P B 4 H20C H 0.681 -0.0883 1.1267 0.08 Uiso 0.393(11) 1 calc PR B 4 H20D H 0.8218 -0.2094 1.1554 0.08 Uiso 0.393(11) 1 calc PR B 4 C21B C 0.688(3) -0.277(3) 1.0974(18) 0.103(7) Uani 0.393(11) 1 d P B 4 H21D H 0.6244 -0.3098 1.166 0.155 Uiso 0.393(11) 1 calc PR B 4 H21E H 0.765 -0.358 1.0779 0.155 Uiso 0.393(11) 1 calc PR B 4 H21F H 0.6264 -0.2361 1.045 0.155 Uiso 0.393(11) 1 calc PR B 4 C22 C 0.7647(4) 0.3529(3) 0.7679(3) 0.0649(9) Uani 1 1 d . . . C23 C 0.9509(5) 0.4832(4) 0.7303(3) 0.0814(11) Uani 1 1 d . . . H23A H 0.9828 0.4324 0.7968 0.098 Uiso 1 1 calc R . . H23B H 0.8773 0.5719 0.7409 0.098 Uiso 1 1 calc R . . C24 C 1.0802(5) 0.5179(6) 0.6474(4) 0.1135(18) Uani 1 1 d . . . H24A H 1.0482 0.5622 0.5803 0.136 Uiso 1 1 calc R . . H24B H 1.1551 0.4288 0.6399 0.136 Uiso 1 1 calc R . . C25 C 1.1517(5) 0.6185(5) 0.6696(4) 0.0981(14) Uani 1 1 d . . . H25A H 1.2371 0.6391 0.612 0.147 Uiso 1 1 calc R . . H25B H 1.186 0.574 0.735 0.147 Uiso 1 1 calc R . . H25C H 1.0784 0.7074 0.6761 0.147 Uiso 1 1 calc R . . O1 O 0.5459(3) -0.0989(2) 0.61514(17) 0.0677(7) Uani 1 1 d . . . O2 O 0.3363(3) 0.0634(2) 0.65374(18) 0.0697(7) Uani 1 1 d . A . O3 O 0.7756(3) -0.2001(3) 0.7894(2) 0.0768(7) Uani 1 1 d . . . O4 O 0.5241(3) -0.1516(2) 0.84722(18) 0.0686(7) Uani 1 1 d . . . O5A O 0.9307(10) 0.0809(8) 0.8348(8) 0.108(3) Uani 0.607(11) 1 d P B 3 O6A O 0.7119(13) -0.0373(19) 0.9514(10) 0.071(3) Uani 0.607(11) 1 d P B 3 O5B O 0.8743(9) 0.1004(8) 0.8926(6) 0.059(2) Uani 0.393(11) 1 d P B 4 O6B O 0.7564(18) -0.025(3) 0.9284(13) 0.057(3) Uani 0.393(11) 1 d P B 4 O7 O 0.7070(4) 0.3883(3) 0.8480(2) 0.0907(9) Uani 1 1 d . . . O8 O 0.8824(3) 0.3931(3) 0.7006(2) 0.0783(8) 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 0.060(2) 0.0620(19) 0.0609(18) -0.0226(16) -0.0072(16) -0.0222(16) C2 0.058(2) 0.0596(18) 0.0655(19) -0.0214(16) -0.0081(16) -0.0186(16) C3 0.059(2) 0.0596(19) 0.073(2) -0.0203(17) -0.0177(17) -0.0160(16) C4 0.061(2) 0.064(2) 0.0679(19) -0.0215(17) -0.0154(17) -0.0198(16) C5 0.058(2) 0.0593(18) 0.0626(18) -0.0222(16) -0.0100(16) -0.0199(16) C6 0.062(2) 0.0610(19) 0.0584(18) -0.0209(15) -0.0079(16) -0.0208(16) C7 0.060(2) 0.066(2) 0.0619(18) -0.0250(16) -0.0085(16) -0.0244(16) C8 0.063(2) 0.0574(18) 0.0608(18) -0.0212(16) -0.0098(16) -0.0210(16) C9 0.063(2) 0.0645(19) 0.0660(19) -0.0259(17) -0.0122(17) -0.0241(16) C10 0.066(2) 0.067(2) 0.0501(17) -0.0175(16) -0.0129(16) -0.0201(18) C11 0.077(3) 0.074(2) 0.073(2) -0.0147(18) -0.028(2) -0.0306(19) C12A 0.074(8) 0.096(9) 0.055(6) -0.030(7) -0.003(6) -0.039(6) C13A 0.079(6) 0.101(7) 0.104(7) -0.036(5) -0.037(5) -0.017(5) C12B 0.067(6) 0.102(7) 0.063(6) -0.032(5) -0.002(5) -0.037(5) C13B 0.096(7) 0.092(7) 0.083(6) -0.017(5) -0.029(5) -0.031(5) C14 0.069(2) 0.067(2) 0.0616(19) -0.0227(17) -0.0133(18) -0.021(2) C15 0.101(3) 0.071(2) 0.090(3) -0.002(2) -0.031(2) -0.040(2) C16 0.111(4) 0.089(3) 0.083(3) -0.009(2) -0.025(3) -0.055(3) C17 0.096(3) 0.128(4) 0.075(2) -0.025(2) -0.013(2) -0.058(3) C18 0.105(4) 0.057(2) 0.112(4) -0.016(2) -0.055(3) -0.019(2) C19A 0.112(8) 0.058(5) 0.072(6) 0.003(4) -0.044(6) -0.016(6) C20A 0.111(10) 0.060(7) 0.089(6) -0.004(5) -0.043(7) -0.017(6) C21A 0.122(8) 0.080(5) 0.106(6) -0.014(4) -0.045(6) -0.033(5) C19B 0.072(8) 0.079(7) 0.068(8) -0.004(6) -0.025(6) -0.022(7) C20B 0.072(7) 0.052(7) 0.072(7) -0.012(6) -0.019(6) -0.006(6) C21B 0.139(18) 0.125(15) 0.062(7) -0.021(8) -0.001(8) -0.075(12) C22 0.071(2) 0.0595(19) 0.076(2) -0.0182(18) -0.029(2) -0.0167(18) C23 0.084(3) 0.076(2) 0.107(3) -0.031(2) -0.035(2) -0.027(2) C24 0.080(3) 0.136(4) 0.156(4) -0.092(4) 0.021(3) -0.057(3) C25 0.084(3) 0.103(3) 0.131(4) -0.052(3) -0.012(3) -0.042(3) O1 0.0773(17) 0.0658(14) 0.0712(14) -0.0268(12) -0.0195(12) -0.0186(12) O2 0.0697(17) 0.0697(14) 0.0836(16) -0.0282(13) -0.0172(13) -0.0257(13) O3 0.0763(19) 0.0661(14) 0.0909(17) -0.0245(14) -0.0145(15) -0.0177(14) O4 0.0721(17) 0.0669(14) 0.0730(14) -0.0159(12) -0.0156(12) -0.0261(12) O5A 0.105(6) 0.111(5) 0.123(6) 0.019(5) -0.069(5) -0.051(4) O6A 0.075(7) 0.072(4) 0.063(5) -0.013(4) -0.008(4) -0.024(6) O5B 0.068(5) 0.071(4) 0.049(4) -0.017(3) -0.007(3) -0.035(3) O6B 0.045(7) 0.080(9) 0.047(7) -0.013(7) -0.012(5) -0.013(6) O7 0.126(3) 0.101(2) 0.0693(16) -0.0212(15) -0.0213(16) -0.0623(18) O8 0.0639(16) 0.0808(16) 0.1115(19) -0.0505(15) -0.0117(15) -0.0266(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.362(5) . ? C1 C6 1.449(4) . ? C1 C10 1.506(4) . ? C2 C3 1.445(4) . ? C2 C14 1.509(5) . ? C3 C4 1.369(4) . ? C3 C18 1.481(5) . ? C4 C5 1.426(5) . ? C4 C22 1.512(4) . ? C5 C9 1.395(4) . ? C5 C6 1.448(4) . ? C6 C7 1.382(4) . ? C7 C8 1.411(4) . ? C7 H7 0.95 . ? C8 C9 1.389(5) 2_666 ? C8 C8 1.443(6) 2_666 ? C9 C8 1.389(5) 2_666 ? C9 H9 0.95 . ? C10 O1 1.198(4) . ? C10 O2 1.329(4) . ? C11 O2 1.460(4) . ? C11 C12B 1.474(11) . ? C11 C12A 1.517(14) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C11 H11C 0.99 . ? C11 H11D 0.99 . ? C12A C13A 1.516(12) . ? C12A H12A 0.99 . ? C12A H12B 0.99 . ? C13A H13A 0.98 . ? C13A H13B 0.98 . ? C13A H13C 0.98 . ? C12B C13B 1.540(14) . ? C12B H12C 0.99 . ? C12B H12D 0.99 . ? C13B H13D 0.98 . ? C13B H13E 0.98 . ? C13B H13F 0.98 . ? C14 O3 1.203(4) . ? C14 O4 1.325(4) . ? C15 O4 1.476(4) . ? C15 C16 1.513(5) . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C16 C17 1.494(6) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? C18 O6B 1.090(19) . ? C18 O5B 1.189(8) . ? C18 O5A 1.313(8) . ? C18 O6A 1.491(11) . ? C19A O6A 1.437(17) . ? C19A C20A 1.557(13) . ? C19A H19A 0.99 . ? C19A H19B 0.99 . ? C20A C21A 1.479(16) . ? C20A H20A 0.99 . ? C20A H20B 0.99 . ? C21A H21A 0.98 . ? C21A H21B 0.98 . ? C21A H21C 0.98 . ? C19B O6B 1.49(2) . ? C19B C20B 1.491(17) . ? C19B H19C 0.99 . ? C19B H19D 0.99 . ? C20B C21B 1.501(19) . ? C20B H20C 0.99 . ? C20B H20D 0.99 . ? C21B H21D 0.98 . ? C21B H21E 0.98 . ? C21B H21F 0.98 . ? C22 O7 1.193(4) . ? C22 O8 1.311(4) . ? C23 O8 1.461(4) . ? C23 C24 1.464(6) . ? C23 H23A 0.99 . ? C23 H23B 0.99 . ? C24 C25 1.514(5) . ? C24 H24A 0.99 . ? C24 H24B 0.99 . ? C25 H25A 0.98 . ? C25 H25B 0.98 . ? C25 H25C 0.98 . ? O5B O6B 1.79(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 C2 C1 C6 121.2(3) . . ? C2 C1 C10 118.7(3) . . ? C6 C1 C10 120.0(3) . . ? C1 C2 C3 120.7(3) . . ? C1 C2 C14 120.3(3) . . ? C3 C2 C14 119.0(3) . . ? C4 C3 C2 119.4(3) . . ? C4 C3 C18 118.6(3) . . ? C2 C3 C18 122.0(3) . . ? C3 C4 C5 122.0(3) . . ? C3 C4 C22 119.3(3) . . ? C5 C4 C22 118.6(3) . . ? C9 C5 C4 122.5(3) . . ? C9 C5 C6 118.7(3) . . ? C4 C5 C6 118.8(3) . . ? C7 C6 C5 119.1(3) . . ? C7 C6 C1 123.1(3) . . ? C5 C6 C1 117.8(3) . . ? C6 C7 C8 122.3(3) . . ? C6 C7 H7 118.8 . . ? C8 C7 H7 118.8 . . ? C9 C8 C7 122.6(3) 2_666 . ? C9 C8 C8 119.0(3) 2_666 2_666 ? C7 C8 C8 118.4(4) . 2_666 ? C8 C9 C5 122.5(3) 2_666 . ? C8 C9 H9 118.8 2_666 . ? C5 C9 H9 118.8 . . ? O1 C10 O2 125.2(3) . . ? O1 C10 C1 124.2(3) . . ? O2 C10 C1 110.6(3) . . ? O2 C11 C12B 111.9(5) . . ? O2 C11 C12A 102.0(4) . . ? C12B C11 C12A 29.2(3) . . ? O2 C11 H11A 111.4 . . ? C12B C11 H11A 82.2 . . ? C12A C11 H11A 111.4 . . ? O2 C11 H11B 111.4 . . ? C12B C11 H11B 126.5 . . ? C12A C11 H11B 111.4 . . ? H11A C11 H11B 109.2 . . ? O2 C11 H11C 109.2 . . ? C12B C11 H11C 109.2 . . ? C12A C11 H11C 136.9 . . ? H11A C11 H11C 29.1 . . ? H11B C11 H11C 84.1 . . ? O2 C11 H11D 109.2 . . ? C12B C11 H11D 109.2 . . ? C12A C11 H11D 88.1 . . ? H11A C11 H11D 129.2 . . ? H11B C11 H11D 25.1 . . ? H11C C11 H11D 107.9 . . ? C13A C12A C11 108.2(8) . . ? C13A C12A H12A 110.1 . . ? C11 C12A H12A 110.1 . . ? C13A C12A H12B 110.1 . . ? C11 C12A H12B 110.1 . . ? H12A C12A H12B 108.4 . . ? C12A C13A H13A 109.5 . . ? C12A C13A H13B 109.5 . . ? H13A C13A H13B 109.5 . . ? C12A C13A H13C 109.5 . . ? H13A C13A H13C 109.5 . . ? H13B C13A H13C 109.5 . . ? C11 C12B C13B 112.3(8) . . ? C11 C12B H12C 109.2 . . ? C13B C12B H12C 109.2 . . ? C11 C12B H12D 109.2 . . ? C13B C12B H12D 109.2 . . ? H12C C12B H12D 107.9 . . ? C12B C13B H13D 109.5 . . ? C12B C13B H13E 109.5 . . ? H13D C13B H13E 109.5 . . ? C12B C13B H13F 109.5 . . ? H13D C13B H13F 109.5 . . ? H13E C13B H13F 109.5 . . ? O3 C14 O4 127.2(3) . . ? O3 C14 C2 122.3(3) . . ? O4 C14 C2 110.5(3) . . ? O4 C15 C16 108.2(3) . . ? O4 C15 H15A 110.1 . . ? C16 C15 H15A 110.1 . . ? O4 C15 H15B 110.1 . . ? C16 C15 H15B 110.1 . . ? H15A C15 H15B 108.4 . . ? C17 C16 C15 113.8(4) . . ? C17 C16 H16A 108.8 . . ? C15 C16 H16A 108.8 . . ? C17 C16 H16B 108.8 . . ? C15 C16 H16B 108.8 . . ? H16A C16 H16B 107.7 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O6B C18 O5B 103.6(12) . . ? O6B C18 O5A 123.8(10) . . ? O5B C18 O5A 40.1(4) . . ? O6B C18 C3 119.1(9) . . ? O5B C18 C3 133.8(6) . . ? O5A C18 C3 114.3(5) . . ? O6B C18 O6A 11.5(16) . . ? O5B C18 O6A 109.4(9) . . ? O5A C18 O6A 134.5(7) . . ? C3 C18 O6A 110.0(7) . . ? O6A C19A C20A 108.3(9) . . ? O6A C19A H19A 110 . . ? C20A C19A H19A 110 . . ? O6A C19A H19B 110 . . ? C20A C19A H19B 110 . . ? H19A C19A H19B 108.4 . . ? C21A C20A C19A 111.5(11) . . ? C21A C20A H20A 109.3 . . ? C19A C20A H20A 109.3 . . ? C21A C20A H20B 109.3 . . ? C19A C20A H20B 109.3 . . ? H20A C20A H20B 108 . . ? C20A C21A H21A 109.5 . . ? C20A C21A H21B 109.5 . . ? H21A C21A H21B 109.5 . . ? C20A C21A H21C 109.5 . . ? H21A C21A H21C 109.5 . . ? H21B C21A H21C 109.5 . . ? O6B C19B C20B 106.5(10) . . ? O6B C19B H19C 110.4 . . ? C20B C19B H19C 110.4 . . ? O6B C19B H19D 110.4 . . ? C20B C19B H19D 110.4 . . ? H19C C19B H19D 108.6 . . ? C19B C20B C21B 115.7(13) . . ? C19B C20B H20C 108.4 . . ? C21B C20B H20C 108.4 . . ? C19B C20B H20D 108.4 . . ? C21B C20B H20D 108.4 . . ? H20C C20B H20D 107.4 . . ? C20B C21B H21D 109.5 . . ? C20B C21B H21E 109.5 . . ? H21D C21B H21E 109.5 . . ? C20B C21B H21F 109.5 . . ? H21D C21B H21F 109.5 . . ? H21E C21B H21F 109.5 . . ? O7 C22 O8 125.4(3) . . ? O7 C22 C4 122.0(3) . . ? O8 C22 C4 112.4(3) . . ? O8 C23 C24 109.2(3) . . ? O8 C23 H23A 109.8 . . ? C24 C23 H23A 109.8 . . ? O8 C23 H23B 109.8 . . ? C24 C23 H23B 109.8 . . ? H23A C23 H23B 108.3 . . ? C23 C24 C25 112.3(4) . . ? C23 C24 H24A 109.1 . . ? C25 C24 H24A 109.1 . . ? C23 C24 H24B 109.1 . . ? C25 C24 H24B 109.1 . . ? H24A C24 H24B 107.9 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C10 O2 C11 117.5(3) . . ? C14 O4 C15 117.7(3) . . ? C19A O6A C18 117.9(10) . . ? C18 O5B O6B 36.2(7) . . ? C18 O6B C19B 117.9(13) . . ? C18 O6B O5B 40.2(8) . . ? C19B O6B O5B 81.7(10) . . ? C22 O8 C23 116.2(3) . . ? 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 C6 C1 C2 C3 3.0(5) . . . . ? C10 C1 C2 C3 -179.3(3) . . . . ? C6 C1 C2 C14 -174.9(3) . . . . ? C10 C1 C2 C14 2.7(5) . . . . ? C1 C2 C3 C4 -1.1(5) . . . . ? C14 C2 C3 C4 176.8(3) . . . . ? C1 C2 C3 C18 178.6(4) . . . . ? C14 C2 C3 C18 -3.5(5) . . . . ? C2 C3 C4 C5 -0.2(5) . . . . ? C18 C3 C4 C5 -180.0(4) . . . . ? C2 C3 C4 C22 175.1(3) . . . . ? C18 C3 C4 C22 -4.6(5) . . . . ? C3 C4 C5 C9 -179.6(3) . . . . ? C22 C4 C5 C9 5.0(5) . . . . ? C3 C4 C5 C6 -0.3(5) . . . . ? C22 C4 C5 C6 -175.6(3) . . . . ? C9 C5 C6 C7 1.6(5) . . . . ? C4 C5 C6 C7 -177.7(3) . . . . ? C9 C5 C6 C1 -178.7(3) . . . . ? C4 C5 C6 C1 2.0(5) . . . . ? C2 C1 C6 C7 176.3(3) . . . . ? C10 C1 C6 C7 -1.4(5) . . . . ? C2 C1 C6 C5 -3.4(5) . . . . ? C10 C1 C6 C5 179.0(3) . . . . ? C5 C6 C7 C8 -1.5(5) . . . . ? C1 C6 C7 C8 178.8(3) . . . . ? C6 C7 C8 C9 -179.2(3) . . . 2_666 ? C6 C7 C8 C8 0.6(6) . . . 2_666 ? C4 C5 C9 C8 178.4(3) . . . 2_666 ? C6 C5 C9 C8 -0.9(5) . . . 2_666 ? C2 C1 C10 O1 -55.4(4) . . . . ? C6 C1 C10 O1 122.4(4) . . . . ? C2 C1 C10 O2 123.4(3) . . . . ? C6 C1 C10 O2 -58.9(4) . . . . ? O2 C11 C12A C13A 179.7(6) . . . . ? C12B C11 C12A C13A -66.7(12) . . . . ? O2 C11 C12B C13B 72.9(7) . . . . ? C12A C11 C12B C13B -2.0(9) . . . . ? C1 C2 C14 O3 116.6(4) . . . . ? C3 C2 C14 O3 -61.4(4) . . . . ? C1 C2 C14 O4 -62.5(4) . . . . ? C3 C2 C14 O4 119.6(3) . . . . ? O4 C15 C16 C17 -64.2(4) . . . . ? C4 C3 C18 O6B 145.3(15) . . . . ? C2 C3 C18 O6B -34.4(16) . . . . ? C4 C3 C18 O5B -9.7(10) . . . . ? C2 C3 C18 O5B 170.6(8) . . . . ? C4 C3 C18 O5A -52.8(7) . . . . ? C2 C3 C18 O5A 127.4(6) . . . . ? C4 C3 C18 O6A 137.4(8) . . . . ? C2 C3 C18 O6A -42.3(9) . . . . ? O6A C19A C20A C21A 76.5(11) . . . . ? O6B C19B C20B C21B 65(2) . . . . ? C3 C4 C22 O7 -73.1(5) . . . . ? C5 C4 C22 O7 102.4(4) . . . . ? C3 C4 C22 O8 111.2(4) . . . . ? C5 C4 C22 O8 -73.3(4) . . . . ? O8 C23 C24 C25 176.6(4) . . . . ? O1 C10 O2 C11 -1.5(5) . . . . ? C1 C10 O2 C11 179.7(2) . . . . ? C12B C11 O2 C10 -173.4(5) . . . . ? C12A C11 O2 C10 -144.6(5) . . . . ? O3 C14 O4 C15 -2.8(5) . . . . ? C2 C14 O4 C15 176.2(3) . . . . ? C16 C15 O4 C14 -128.6(4) . . . . ? C20A C19A O6A C18 -148.3(13) . . . . ? O6B C18 O6A C19A 44(8) . . . . ? O5B C18 O6A C19A -17.4(16) . . . . ? O5A C18 O6A C19A 20(2) . . . . ? C3 C18 O6A C19A -172.8(10) . . . . ? O5A C18 O5B O6B -127.0(15) . . . . ? C3 C18 O5B O6B 157.7(15) . . . . ? O6A C18 O5B O6B 10.4(19) . . . . ? O5B C18 O6B C19B -28(2) . . . . ? O5A C18 O6B C19B 10(3) . . . . ? C3 C18 O6B C19B 170.0(13) . . . . ? O6A C18 O6B C19B -150(11) . . . . ? O5A C18 O6B O5B 38.3(9) . . . . ? C3 C18 O6B O5B -161.7(12) . . . . ? O6A C18 O6B O5B -122(9) . . . . ? C20B C19B O6B C18 158.9(19) . . . . ? C20B C19B O6B O5B 140.9(13) . . . . ? C18 O5B O6B C19B 155.0(19) . . . . ? O7 C22 O8 C23 3.1(5) . . . . ? C4 C22 O8 C23 178.6(3) . . . . ? C24 C23 O8 C22 179.8(4) . . . . ? # END of CIF _chemical_name_common 'Octapropyl tetracene-1,2,3,4,7,8,9,10-octacarboxylate'