# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/432 data_tsujimo04 #------------------------------------------------------------------------------ _audit_creation_date 'Tue Sep 7 19:59:39 1999' _audit_creation_method 'from TEXRAY.INF file' _audit_update_record ? #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan' _computing_structure_solution 'DIRDIF92 (PATTY)' _computing_structure_refinement 'teXsan' _computing_publication_material 'teXsan' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _chemical_compound_source ? _chemical_name_common ? _chemical_formula_weight 392.11 _chemical_formula_analytical ? _chemical_formula_sum 'C14 H18 Cl4 O4 ' _chemical_formula_moiety 'C14 H18 Cl4 O4 ' _chemical_formula_structural ? _chemical_melting_point ? #------------------------------------------------------------------------------ _cell_length_a 15.857(3) _cell_length_b 17.205(2) _cell_length_c 13.287(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3624(1) _cell_formula_units_Z 8 _cell_measurement_temperature 296.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.1 _cell_measurement_theta_max 14.1 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_Int_Tables_number 61 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z 1/2-x,-y,1/2+z -x,-y,-z 1/2-x,1/2+y,z x,1/2-y,1/2+z 1/2+x,y,1/2-z #------------------------------------------------------------------------------ _exptl_crystal_description '----------' _exptl_crystal_colour '--------------------' _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616.00 _exptl_absorpt_coefficient_mu 0.667 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 296.2 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% -7.05 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 5 -3 -1 5 -3 0 10 -2 _diffrn_reflns_number 4455 _reflns_number_total 4455 _reflns_number_gt 1102 _reflns_observed_expression >2.0sigma(I) _diffrn_reflns_av_R_equivalents 0.000 _diffrn_reflns_av_sigmaI/netI 0.189 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.01922 _diffrn_orient_matrix_UB_12 0.05211 _diffrn_orient_matrix_UB_13 0.02418 _diffrn_orient_matrix_UB_21 0.04464 _diffrn_orient_matrix_UB_22 -0.00072 _diffrn_orient_matrix_UB_23 0.05315 _diffrn_orient_matrix_UB_31 0.04018 _diffrn_orient_matrix_UB_32 0.02573 _diffrn_orient_matrix_UB_33 -0.04749 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'Cl' 'Cl' 0.148 0.159 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ 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_calc_flags _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.5833(1) 0.6041(1) 0.6929(1) 0.0738(8) Uani 1.00 d . . . Cl2 Cl 0.5645(1) 0.3199(1) 0.8399(2) 0.0812(8) Uani 1.00 d . . . Cl3 Cl 0.9182(1) 0.3445(2) 0.8880(2) 0.0972(9) Uani 1.00 d . . . Cl4 Cl 0.8805(2) 0.6473(1) 0.9449(2) 0.0953(9) Uani 1.00 d . . . O1 O 0.7306(3) 0.5639(3) 1.1277(4) 0.073(2) Uani 1.00 d . . . O2 O 0.5699(3) 0.4467(3) 1.0685(4) 0.072(2) Uani 1.00 d . . . O3 O 0.6684(3) 0.6509(3) 1.0268(3) 0.058(2) Uani 1.00 d . . . O4 O 0.6615(3) 0.3487(3) 1.0755(4) 0.064(2) Uani 1.00 d . . . C1 C 0.7099(4) 0.5350(4) 0.9546(5) 0.037(2) Uani 1.00 d . . . C2 C 0.6457(4) 0.5474(4) 0.8690(5) 0.044(2) Uani 1.00 d . . . C3 C 0.6423(4) 0.4592(4) 0.8528(5) 0.044(2) Uani 1.00 d . . . C4 C 0.6872(4) 0.4464(4) 0.9561(5) 0.037(2) Uani 1.00 d . . . C5 C 0.7805(4) 0.4248(4) 0.9521(5) 0.046(2) Uani 1.00 d . . . C6 C 0.8011(5) 0.5088(4) 0.9208(5) 0.052(3) Uani 1.00 d . . . C7 C 0.6674(5) 0.5998(5) 0.7827(6) 0.065(3) Uani 1.00 d . . . C8 C 0.5562(5) 0.4235(4) 0.8359(6) 0.058(3) Uani 1.00 d . . . C9 C 0.8062(5) 0.3573(5) 0.8862(6) 0.064(3) Uani 1.00 d . . . C10 C 0.8762(5) 0.5462(5) 0.9715(6) 0.072(3) Uani 1.00 d . . . C11 C 0.7050(5) 0.5834(4) 1.0462(7) 0.049(3) Uani 1.00 d . . . C12 C 0.6319(5) 0.4155(4) 1.0383(5) 0.044(3) Uani 1.00 d . . . C13 C 0.6631(6) 0.7054(5) 1.1091(7) 0.086(3) Uani 1.00 d . . . C14 C 0.6085(7) 0.3112(5) 1.1502(7) 0.098(4) Uani 1.00 d . . . H1 H 0.5945 0.5642 0.8979 0.0541 Uiso 1.00 calc . . . H2 H 0.6786 0.4440 0.7992 0.0543 Uiso 1.00 calc . . . H3 H 0.8005 0.4162 1.0193 0.0548 Uiso 1.00 calc . . . H4 H 0.8073 0.5127 0.8499 0.0639 Uiso 1.00 calc . . . H5 H 0.7162 0.5817 0.7500 0.0753 Uiso 1.00 calc . . . H6 H 0.6767 0.6512 0.8075 0.0753 Uiso 1.00 calc . . . H7 H 0.5350 0.4381 0.7717 0.0703 Uiso 1.00 calc . . . H8 H 0.5184 0.4398 0.8867 0.0703 Uiso 1.00 calc . . . H9 H 0.7895 0.3666 0.8207 0.0774 Uiso 1.00 calc . . . H10 H 0.7819 0.3112 0.9124 0.0774 Uiso 1.00 calc . . . H11 H 0.9267 0.5238 0.9465 0.0891 Uiso 1.00 calc . . . H12 H 0.8726 0.5400 1.0414 0.0891 Uiso 1.00 calc . . . H13 H 0.7172 0.7186 1.1299 0.1020 Uiso 1.00 calc . . . H14 H 0.6351 0.7519 1.0831 0.1020 Uiso 1.00 calc . . . H15 H 0.6303 0.6844 1.1603 0.1020 Uiso 1.00 calc . . . H16 H 0.5991 0.3447 1.2036 0.1158 Uiso 1.00 calc . . . H17 H 0.5544 0.3004 1.1170 0.1158 Uiso 1.00 calc . . . H18 H 0.6324 0.2641 1.1695 0.1158 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.079(2) 0.095(2) 0.048(1) 0.013(1) -0.008(1) 0.021(1) Cl2 0.091(2) 0.052(1) 0.101(2) 0.003(1) -0.019(1) -0.017(1) Cl3 0.060(2) 0.134(2) 0.097(2) 0.044(1) 0.025(1) 0.012(2) Cl4 0.085(2) 0.086(2) 0.114(2) -0.030(1) 0.001(2) 0.013(2) O1 0.093(4) 0.078(4) 0.049(4) 0.005(3) -0.015(3) 0.000(3) O2 0.067(4) 0.077(4) 0.073(4) 0.021(3) 0.034(3) 0.012(3) O3 0.082(4) 0.050(4) 0.043(3) 0.004(3) 0.003(3) -0.008(3) O4 0.068(4) 0.066(4) 0.057(4) 0.018(3) 0.019(3) 0.023(3) C1 0.041(4) 0.038(4) 0.032(4) 0.005(3) -0.004(4) 0.005(4) C2 0.049(5) 0.044(5) 0.040(4) -0.001(4) 0.004(4) 0.002(4) C3 0.042(5) 0.060(5) 0.031(4) 0.003(4) 0.000(4) -0.007(4) C4 0.031(4) 0.046(5) 0.035(4) 0.009(3) 0.004(4) 0.002(4) C5 0.040(5) 0.059(6) 0.039(4) 0.014(4) 0.001(4) 0.003(4) C6 0.051(5) 0.059(6) 0.047(5) -0.002(4) 0.003(4) 0.011(4) C7 0.071(6) 0.068(6) 0.055(6) -0.006(5) -0.007(4) 0.011(5) C8 0.059(6) 0.047(5) 0.068(5) 0.007(4) -0.017(4) -0.007(4) C9 0.060(6) 0.078(6) 0.055(5) 0.027(5) 0.009(4) 0.006(5) C10 0.056(6) 0.092(7) 0.069(6) -0.006(5) -0.007(5) 0.010(5) C11 0.058(5) 0.041(6) 0.050(5) 0.000(4) 0.000(5) 0.006(5) C12 0.047(5) 0.047(5) 0.038(5) 0.002(4) 0.004(4) -0.004(4) C13 0.113(8) 0.068(6) 0.077(6) 0.006(5) 0.004(6) -0.018(6) C14 0.117(8) 0.081(7) 0.095(7) 0.007(6) 0.044(6) 0.039(6) #------------------------------------------------------------------------------ _refine_special_details ; Refinement based on F against all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F, conventional R-factors (R) are calculated on F, with F set to zero for negative F. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. thus the refinement was done using all reflections. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00123|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1102 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_all ? _refine_ls_wR_factor_ref 0.0547 _refine_ls_wR_factor_gt 0.0547 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_shift/su_max 0.0220 _refine_ls_shift/su_mean 0.0040 _refine_diff_density_min -0.24 _refine_diff_density_max 0.22 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag CL1 C7 1.792(8) 1_555 1_555 yes CL2 C8 1.789(7) 1_555 1_555 yes CL3 C9 1.790(8) 1_555 1_555 yes CL4 C10 1.777(9) 1_555 1_555 yes O1 C11 1.205(8) 1_555 1_555 yes O2 C12 1.190(8) 1_555 1_555 yes O3 C11 1.324(8) 1_555 1_555 yes O3 C13 1.442(9) 1_555 1_555 yes O4 C12 1.337(8) 1_555 1_555 yes O4 C14 1.452(9) 1_555 1_555 yes C1 C2 1.541(9) 1_555 1_555 yes C1 C4 1.566(9) 1_555 1_555 yes C1 C6 1.581(9) 1_555 1_555 yes C1 C11 1.477(10) 1_555 1_555 yes C2 C3 1.534(10) 1_555 1_555 yes C2 C7 1.500(9) 1_555 1_555 yes C3 C4 1.563(9) 1_555 1_555 yes C3 C8 1.512(9) 1_555 1_555 yes C4 C5 1.526(9) 1_555 1_555 yes C4 C12 1.498(9) 1_555 1_555 yes C5 C6 1.539(9) 1_555 1_555 yes C5 C9 1.510(9) 1_555 1_555 yes C6 C10 1.511(10) 1_555 1_555 yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O3 C13 116.6(6) 1_555 1_555 1_555 yes C12 O4 C14 115.5(6) 1_555 1_555 1_555 yes C2 C1 C4 89.6(5) 1_555 1_555 1_555 yes C2 C1 C6 115.8(5) 1_555 1_555 1_555 yes C2 C1 C11 119.6(6) 1_555 1_555 1_555 yes C4 C1 C6 86.4(5) 1_555 1_555 1_555 yes C4 C1 C11 121.7(6) 1_555 1_555 1_555 yes C6 C1 C11 116.3(6) 1_555 1_555 1_555 yes C1 C2 C3 89.4(5) 1_555 1_555 1_555 yes C1 C2 C7 119.7(6) 1_555 1_555 1_555 yes C1 C2 H1 108.2(6) 1_555 1_555 1_555 no C3 C2 C7 119.7(6) 1_555 1_555 1_555 yes C3 C2 H1 109.3(6) 1_555 1_555 1_555 no C7 C2 H1 108.9(6) 1_555 1_555 1_555 no C2 C3 C4 90.0(5) 1_555 1_555 1_555 yes C2 C3 C8 117.0(6) 1_555 1_555 1_555 yes C2 C3 H2 110.8(6) 1_555 1_555 1_555 no C4 C3 C8 119.0(6) 1_555 1_555 1_555 yes C4 C3 H2 110.0(6) 1_555 1_555 1_555 no C8 C3 H2 108.8(6) 1_555 1_555 1_555 no C1 C4 C3 87.5(5) 1_555 1_555 1_555 yes C1 C4 C5 90.8(5) 1_555 1_555 1_555 yes C1 C4 C12 119.3(6) 1_555 1_555 1_555 yes C3 C4 C5 116.4(5) 1_555 1_555 1_555 yes C3 C4 C12 115.1(6) 1_555 1_555 1_555 yes C5 C4 C12 120.4(6) 1_555 1_555 1_555 yes C4 C5 C6 89.3(5) 1_555 1_555 1_555 yes C4 C5 C9 118.0(6) 1_555 1_555 1_555 yes C4 C5 H3 109.0(6) 1_555 1_555 1_555 no C6 C5 C9 120.5(6) 1_555 1_555 1_555 yes C6 C5 H3 109.0(7) 1_555 1_555 1_555 no C9 C5 H3 109.4(6) 1_555 1_555 1_555 no C1 C6 C5 89.8(5) 1_555 1_555 1_555 yes C1 C6 C10 118.2(6) 1_555 1_555 1_555 yes C1 C6 H4 110.8(6) 1_555 1_555 1_555 no C5 C6 C10 116.5(6) 1_555 1_555 1_555 yes C5 C6 H4 110.9(7) 1_555 1_555 1_555 no C10 C6 H4 109.3(7) 1_555 1_555 1_555 no CL1 C7 C2 111.3(5) 1_555 1_555 1_555 yes CL1 C7 H5 108.6(6) 1_555 1_555 1_555 no CL1 C7 H6 107.8(6) 1_555 1_555 1_555 no C2 C7 H5 110.1(7) 1_555 1_555 1_555 no C2 C7 H6 109.2(7) 1_555 1_555 1_555 no H5 C7 H6 109.9(8) 1_555 1_555 1_555 no CL2 C8 C3 109.5(5) 1_555 1_555 1_555 yes CL2 C8 H7 108.4(6) 1_555 1_555 1_555 no CL2 C8 H8 108.6(6) 1_555 1_555 1_555 no C3 C8 H7 110.3(7) 1_555 1_555 1_555 no C3 C8 H8 110.3(6) 1_555 1_555 1_555 no H7 C8 H8 109.8(7) 1_555 1_555 1_555 no CL3 C9 C5 110.7(5) 1_555 1_555 1_555 yes CL3 C9 H9 108.5(6) 1_555 1_555 1_555 no CL3 C9 H10 107.2(6) 1_555 1_555 1_555 no C5 C9 H9 109.6(7) 1_555 1_555 1_555 no C5 C9 H10 108.7(7) 1_555 1_555 1_555 no H9 C9 H10 112.0(8) 1_555 1_555 1_555 no CL4 C10 C6 111.0(6) 1_555 1_555 1_555 yes CL4 C10 H11 107.2(6) 1_555 1_555 1_555 no CL4 C10 H12 108.1(7) 1_555 1_555 1_555 no C6 C10 H11 109.7(8) 1_555 1_555 1_555 no C6 C10 H12 110.2(7) 1_555 1_555 1_555 no H11 C10 H12 110.7(8) 1_555 1_555 1_555 no O1 C11 O3 124.6(7) 1_555 1_555 1_555 yes O1 C11 C1 124.4(7) 1_555 1_555 1_555 yes O3 C11 C1 111.0(7) 1_555 1_555 1_555 yes O2 C12 O4 123.7(7) 1_555 1_555 1_555 yes O2 C12 C4 124.6(7) 1_555 1_555 1_555 yes O4 C12 C4 111.7(6) 1_555 1_555 1_555 yes O3 C13 H13 109.4(8) 1_555 1_555 1_555 no O3 C13 H14 106.9(8) 1_555 1_555 1_555 no O3 C13 H15 109.6(7) 1_555 1_555 1_555 no H13 C13 H14 108.9(9) 1_555 1_555 1_555 no H13 C13 H15 113.2(9) 1_555 1_555 1_555 no H14 C13 H15 108.8(9) 1_555 1_555 1_555 no O4 C14 H16 110.0(8) 1_555 1_555 1_555 no O4 C14 H17 106.4(8) 1_555 1_555 1_555 no O4 C14 H18 109.8(8) 1_555 1_555 1_555 no H16 C14 H17 108.7(9) 1_555 1_555 1_555 no H16 C14 H18 113.4(10) 1_555 1_555 1_555 no H17 C14 H18 108.3(9) 1_555 1_555 1_555 no #------------------------------------------------------------------------------ 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 CL1 C7 C2 C1 179.5(5) 1_555 1_555 1_555 1_555 yes CL1 C7 C2 C3 71.3(8) 1_555 1_555 1_555 1_555 yes CL2 C8 C3 C2 -170.3(5) 1_555 1_555 1_555 1_555 yes CL2 C8 C3 C4 -64.0(7) 1_555 1_555 1_555 1_555 yes CL3 C9 C5 C4 177.5(5) 1_555 1_555 1_555 1_555 yes CL3 C9 C5 C6 70.3(7) 1_555 1_555 1_555 1_555 yes CL4 C10 C6 C1 -64.3(7) 1_555 1_555 1_555 1_555 yes CL4 C10 C6 C5 -169.5(5) 1_555 1_555 1_555 1_555 yes O1 C11 O3 C13 2(1) 1_555 1_555 1_555 1_555 yes O1 C11 C1 C2 154.2(7) 1_555 1_555 1_555 1_555 yes O1 C11 C1 C4 44(1) 1_555 1_555 1_555 1_555 yes O1 C11 C1 C6 -58.7(10) 1_555 1_555 1_555 1_555 yes O2 C12 O4 C14 5(1) 1_555 1_555 1_555 1_555 yes O2 C12 C4 C1 43(1) 1_555 1_555 1_555 1_555 yes O2 C12 C4 C3 -58.8(9) 1_555 1_555 1_555 1_555 yes O2 C12 C4 C5 153.5(7) 1_555 1_555 1_555 1_555 yes O3 C11 C1 C2 -25.6(8) 1_555 1_555 1_555 1_555 yes O3 C11 C1 C4 -135.6(6) 1_555 1_555 1_555 1_555 yes O3 C11 C1 C6 121.5(6) 1_555 1_555 1_555 1_555 yes O4 C12 C4 C1 -135.7(6) 1_555 1_555 1_555 1_555 yes O4 C12 C4 C3 122.3(6) 1_555 1_555 1_555 1_555 yes O4 C12 C4 C5 -25.4(9) 1_555 1_555 1_555 1_555 yes C1 C2 C3 C4 14.3(5) 1_555 1_555 1_555 1_555 yes C1 C2 C3 C8 137.2(6) 1_555 1_555 1_555 1_555 yes C1 C4 C3 C2 -14.1(5) 1_555 1_555 1_555 1_555 yes C1 C4 C3 C8 -135.3(6) 1_555 1_555 1_555 1_555 yes C1 C4 C5 C6 -14.9(5) 1_555 1_555 1_555 1_555 yes C1 C4 C5 C9 -139.6(6) 1_555 1_555 1_555 1_555 yes C1 C6 C5 C4 14.8(5) 1_555 1_555 1_555 1_555 yes C1 C6 C5 C9 137.3(6) 1_555 1_555 1_555 1_555 yes C1 C11 O3 C13 -177.2(6) 1_555 1_555 1_555 1_555 yes C2 C1 C4 C3 14.0(5) 1_555 1_555 1_555 1_555 yes C2 C1 C4 C5 130.4(5) 1_555 1_555 1_555 1_555 yes C2 C1 C4 C12 -103.5(6) 1_555 1_555 1_555 1_555 yes C2 C1 C6 C5 -102.2(6) 1_555 1_555 1_555 1_555 yes C2 C1 C6 C10 137.5(6) 1_555 1_555 1_555 1_555 yes C2 C3 C4 C5 -103.7(6) 1_555 1_555 1_555 1_555 yes C2 C3 C4 C12 107.3(6) 1_555 1_555 1_555 1_555 yes C3 C2 C1 C4 -14.3(5) 1_555 1_555 1_555 1_555 yes C3 C2 C1 C6 71.5(7) 1_555 1_555 1_555 1_555 yes C3 C2 C1 C11 -141.2(6) 1_555 1_555 1_555 1_555 yes C3 C4 C1 C6 -101.9(4) 1_555 1_555 1_555 1_555 yes C3 C4 C1 C11 139.2(6) 1_555 1_555 1_555 1_555 yes C3 C4 C5 C6 72.6(6) 1_555 1_555 1_555 1_555 yes C3 C4 C5 C9 -52.0(9) 1_555 1_555 1_555 1_555 yes C4 C1 C2 C7 -138.6(6) 1_555 1_555 1_555 1_555 yes C4 C1 C6 C5 -14.4(5) 1_555 1_555 1_555 1_555 yes C4 C1 C6 C10 -134.8(7) 1_555 1_555 1_555 1_555 yes C4 C3 C2 C7 138.7(6) 1_555 1_555 1_555 1_555 yes C4 C5 C6 C10 136.6(6) 1_555 1_555 1_555 1_555 yes C4 C12 O4 C14 -175.4(6) 1_555 1_555 1_555 1_555 yes C5 C4 C1 C6 14.6(5) 1_555 1_555 1_555 1_555 yes C5 C4 C1 C11 -104.4(7) 1_555 1_555 1_555 1_555 yes C5 C4 C3 C8 135.1(6) 1_555 1_555 1_555 1_555 yes C5 C6 C1 C11 109.4(6) 1_555 1_555 1_555 1_555 yes C6 C1 C2 C7 -52.9(9) 1_555 1_555 1_555 1_555 yes C6 C1 C4 C12 140.6(6) 1_555 1_555 1_555 1_555 yes C6 C5 C4 C12 -140.1(6) 1_555 1_555 1_555 1_555 yes C7 C2 C1 C11 94.4(8) 1_555 1_555 1_555 1_555 yes C7 C2 C3 C8 -98.4(8) 1_555 1_555 1_555 1_555 yes C8 C3 C4 C12 -14.0(9) 1_555 1_555 1_555 1_555 yes C9 C5 C4 C12 95.3(8) 1_555 1_555 1_555 1_555 yes C9 C5 C6 C10 -100.9(8) 1_555 1_555 1_555 1_555 yes C10 C6 C1 C11 -10.9(9) 1_555 1_555 1_555 1_555 yes C11 C1 C4 C12 21.7(9) 1_555 1_555 1_555 1_555 yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag CL2 CL4 3.395(3) 1_555 6_645 ? CL2 C14 3.453(9) 1_555 7_554 ? O2 C8 3.256(9) 1_555 5_667 ? O2 O2 3.40(1) 1_555 5_667 ? O2 C2 3.519(9) 1_555 5_667 ? #------------------------------------------------------------------------------ _publ_contact_author_name ' ENTER NAME' _publ_contact_author_address ; ENTER ADDRESS ; _publ_contact_author_email ' ENTER EMAIL ADDRESS ' _publ_contact_author_fax ' ENTER FAX NUMBER ' _publ_contact_author_phone ' ENTER PHONE NUMBER ' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_journal ' ENTER JOURNAL NAME HERE' _publ_requested_category ' CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? _publ_section_title ; ENTER SECTION TITLE ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; _publ_section_synopsis ; ENTER SYNOPSIS ; _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_experimental ; ENTER EXPERIMENTAL SECTION ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation, Rigaku Corporation. (1998). teXsan. Single Crystal Structure Analysis Software. Version 1.9. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; ENTER SPECIAL DETAILS OF THE REFINEMENT ; #compound 11 data_sano_Dewar_pentacene_-70_d #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C30 H26 O2 ' _chemical_formula_moiety 'C30 H26 O2 ' _chemical_formula_weight 418.53 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z _cell_length_a 11.4190(8) _cell_length_b 11.0908(5) _cell_length_c 17.519(2) _cell_angle_alpha 90 _cell_angle_beta 90.025(3) _cell_angle_gamma 90 _cell_volume 2218.7(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_measurement_temperature 203 #------------------------------------------------------------------------------ _exptl_crystal_description 'unknown' _exptl_crystal_colour 'unknown' _exptl_crystal_size_max 0.000 _exptl_crystal_size_mid 0.000 _exptl_crystal_size_min 0.000 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type ? _diffrn_reflns_number 16262 _diffrn_reflns_av_R_equivalents 0.030 _diffrn_reflns_theta_max 26.00 _diffrn_measured_fraction_theta_max 0.9812 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.9812 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 3.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 3.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4285 _reflns_number_gt 3346 _reflns_threshold_expression F^2^>3.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0619 _refine_ls_wR_factor_ref 0.0769 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 3346 _refine_ls_number_parameters 289 _refine_ls_goodness_of_fit_ref 1.925 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00063|Fo|^2^]' _refine_ls_shift/su_max 0.0017 _refine_diff_density_max 0.16 _refine_diff_density_min -0.15 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack 0.00000 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 0.32226(9) 0.42727(9) 0.29754(7) 0.0327(3) Uani 1.00 d . . . O(2) O 0.11617(9) 0.43148(9) 0.31385(7) 0.0383(3) Uani 1.00 d . . . C(1) C 0.3040(1) 0.2586(1) 0.38370(10) 0.0289(4) Uani 1.00 d . . . C(2) C 0.3119(1) 0.3290(1) 0.45870(9) 0.0289(4) Uani 1.00 d . . . C(3) C 0.3880(1) 0.3740(1) 0.51058(9) 0.0297(4) Uani 1.00 d . . . C(4) C 0.3399(1) 0.4250(1) 0.57845(10) 0.0319(4) Uani 1.00 d . . . C(5) C 0.4118(1) 0.4706(1) 0.6378(1) 0.0376(4) Uani 1.00 d . . . C(6) C 0.3650(2) 0.5169(2) 0.7029(1) 0.0452(5) Uani 1.00 d . . . C(7) C 0.2433(2) 0.5207(2) 0.7132(1) 0.0462(5) Uani 1.00 d . . . C(8) C 0.1708(2) 0.4782(1) 0.6579(1) 0.0409(4) Uani 1.00 d . . . C(9) C 0.2153(1) 0.4289(1) 0.58883(10) 0.0326(4) Uani 1.00 d . . . C(10) C 0.1392(1) 0.3823(1) 0.5321(1) 0.0341(4) Uani 1.00 d . . . C(11) C 0.1894(1) 0.3321(1) 0.46875(10) 0.0305(4) Uani 1.00 d . . . C(12) C 0.1638(1) 0.2621(1) 0.39515(10) 0.0306(4) Uani 1.00 d . . . C(13) C 0.1722(1) 0.1252(1) 0.40685(9) 0.0284(4) Uani 1.00 d . . . C(14) C 0.1082(1) 0.0249(1) 0.42132(9) 0.0288(4) Uani 1.00 d . . . C(15) C 0.1710(1) -0.0860(1) 0.42786(9) 0.0287(4) Uani 1.00 d . . . C(16) C 0.1134(1) -0.1947(1) 0.4454(1) 0.0376(4) Uani 1.00 d . . . C(17) C 0.1739(2) -0.3001(1) 0.4542(1) 0.0476(5) Uani 1.00 d . . . C(18) C 0.2949(2) -0.3028(1) 0.4443(1) 0.0460(5) Uani 1.00 d . . . C(19) C 0.3544(1) -0.2003(1) 0.4260(1) 0.0365(4) Uani 1.00 d . . . C(20) C 0.2959(1) -0.0883(1) 0.41859(9) 0.0297(4) Uani 1.00 d . . . C(21) C 0.3591(1) 0.0201(1) 0.40280(9) 0.0302(4) Uani 1.00 d . . . C(22) C 0.2951(1) 0.1226(1) 0.39731(9) 0.0295(4) Uani 1.00 d . . . C(23) C 0.3571(1) 0.3056(1) 0.31109(10) 0.0320(4) Uani 1.00 d . . . C(24) C 0.0854(1) 0.3112(1) 0.3339(1) 0.0381(4) Uani 1.00 d . . . C(25) C 0.2113(1) 0.4506(1) 0.2624(1) 0.0336(4) Uani 1.00 d . . . C(26) C 0.1966(2) 0.3833(2) 0.1868(1) 0.0445(5) Uani 1.00 d . . . C(27) C 0.2892(2) 0.4211(2) 0.1288(1) 0.0544(5) Uani 1.00 d . . . C(28) C 0.2899(2) 0.5565(2) 0.1171(1) 0.0589(6) Uani 1.00 d . . . C(29) C 0.3047(2) 0.6238(2) 0.1915(1) 0.0508(5) Uani 1.00 d . . . C(30) C 0.2110(2) 0.5860(1) 0.2487(1) 0.0430(5) Uani 1.00 d . . . H(1) H 0.4715 0.3725 0.5021 0.0357 Uiso 1.00 calc . . . H(2) H 0.4959 0.4684 0.6316 0.0467 Uiso 1.00 calc . . . H(3) H 0.4158 0.5467 0.7427 0.0552 Uiso 1.00 calc . . . H(4) H 0.2111 0.5537 0.7592 0.0554 Uiso 1.00 calc . . . H(5) H 0.0873 0.4802 0.6653 0.0499 Uiso 1.00 calc . . . H(6) H 0.0558 0.3859 0.5381 0.0404 Uiso 1.00 calc . . . H(7) H 0.0246 0.0282 0.4263 0.0369 Uiso 1.00 calc . . . H(8) H 0.0300 -0.1938 0.4516 0.0442 Uiso 1.00 calc . . . H(9) H 0.1323 -0.3721 0.4682 0.0542 Uiso 1.00 calc . . . H(10) H 0.3374 -0.3768 0.4515 0.0551 Uiso 1.00 calc . . . H(11) H 0.4373 -0.2043 0.4177 0.0453 Uiso 1.00 calc . . . H(12) H 0.4427 0.0203 0.3959 0.0349 Uiso 1.00 calc . . . H(13) H 0.3321 0.2563 0.2685 0.0398 Uiso 1.00 calc . . . H(14) H 0.4408 0.3011 0.3134 0.0398 Uiso 1.00 calc . . . H(15) H 0.0061 0.3087 0.3510 0.0483 Uiso 1.00 calc . . . H(16) H 0.0915 0.2603 0.2893 0.0483 Uiso 1.00 calc . . . H(17) H 0.2024 0.2984 0.1962 0.0535 Uiso 1.00 calc . . . H(18) H 0.1207 0.4001 0.1668 0.0535 Uiso 1.00 calc . . . H(19) H 0.3646 0.3971 0.1475 0.0680 Uiso 1.00 calc . . . H(20) H 0.2748 0.3816 0.0818 0.0680 Uiso 1.00 calc . . . H(21) H 0.3513 0.5781 0.0827 0.0701 Uiso 1.00 calc . . . H(22) H 0.2167 0.5803 0.0944 0.0701 Uiso 1.00 calc . . . H(23) H 0.3805 0.6047 0.2126 0.0598 Uiso 1.00 calc . . . H(24) H 0.3011 0.7083 0.1833 0.0598 Uiso 1.00 calc . . . H(25) H 0.1358 0.6094 0.2296 0.0533 Uiso 1.00 calc . . . H(26) H 0.2234 0.6263 0.2964 0.0533 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0337(5) 0.0256(5) 0.0389(6) -0.0021(4) -0.0043(5) 0.0060(5) O(2) 0.0331(6) 0.0287(5) 0.0530(7) 0.0036(5) 0.0022(5) 0.0094(5) C(1) 0.0230(7) 0.0231(6) 0.0408(8) 0.0010(6) -0.0012(7) 0.0036(6) C(2) 0.0267(7) 0.0204(7) 0.0396(8) -0.0001(6) 0.0024(6) 0.0060(6) C(3) 0.0226(7) 0.0261(7) 0.0403(8) -0.0008(6) 0.0021(6) 0.0089(6) C(4) 0.0318(7) 0.0230(7) 0.0408(8) -0.0024(6) 0.0024(7) 0.0085(6) C(5) 0.0382(9) 0.0331(8) 0.0416(9) -0.0056(7) -0.0014(7) 0.0058(7) C(6) 0.0546(10) 0.0419(10) 0.0391(10) -0.0102(8) 0.0007(8) 0.0025(8) C(7) 0.061(1) 0.0364(9) 0.0413(10) -0.0017(8) 0.0114(8) -0.0024(7) C(8) 0.0388(9) 0.0305(8) 0.053(1) 0.0027(7) 0.0138(7) 0.0036(7) C(9) 0.0340(7) 0.0187(7) 0.0452(9) -0.0006(6) 0.0057(7) 0.0070(6) C(10) 0.0247(7) 0.0226(7) 0.0549(10) 0.0017(6) 0.0061(7) 0.0041(7) C(11) 0.0269(7) 0.0194(7) 0.0452(9) 0.0006(6) -0.0003(7) 0.0077(6) C(12) 0.0229(7) 0.0239(7) 0.0449(9) -0.0008(6) 0.0015(7) 0.0043(6) C(13) 0.0267(7) 0.0240(6) 0.0344(8) 0.0007(6) 0.0003(7) 0.0026(6) C(14) 0.0244(7) 0.0276(7) 0.0343(8) 0.0004(5) -0.0007(6) 0.0009(6) C(15) 0.0310(7) 0.0253(7) 0.0297(8) 0.0003(6) -0.0014(7) 0.0007(6) C(16) 0.0287(8) 0.0285(7) 0.056(1) -0.0029(6) -0.0007(8) 0.0046(8) C(17) 0.0386(9) 0.0239(8) 0.080(1) -0.0055(6) -0.0046(9) 0.0104(8) C(18) 0.0414(9) 0.0245(8) 0.072(1) 0.0059(7) -0.0093(9) 0.0066(8) C(19) 0.0310(8) 0.0285(7) 0.050(1) 0.0051(6) -0.0005(8) 0.0023(7) C(20) 0.0304(7) 0.0264(7) 0.0324(8) 0.0025(6) 0.0000(7) 0.0017(6) C(21) 0.0277(8) 0.0282(7) 0.0347(8) 0.0006(6) 0.0018(7) 0.0035(6) C(22) 0.0288(7) 0.0265(7) 0.0333(8) -0.0008(6) 0.0018(7) 0.0031(6) C(23) 0.0291(8) 0.0258(7) 0.0410(9) 0.0004(6) 0.0020(7) 0.0071(6) C(24) 0.0275(8) 0.0305(8) 0.056(1) -0.0005(6) -0.0065(7) 0.0094(7) C(25) 0.0319(8) 0.0288(7) 0.0402(9) 0.0019(6) -0.0042(6) 0.0037(7) C(26) 0.0459(10) 0.0407(9) 0.0468(10) -0.0026(8) -0.0125(8) -0.0040(8) C(27) 0.064(1) 0.064(1) 0.0354(10) 0.0010(10) -0.0026(9) -0.0087(9) C(28) 0.060(1) 0.074(1) 0.044(1) 0.001(1) -0.0046(10) 0.0178(9) C(29) 0.063(1) 0.0341(9) 0.055(1) -0.0023(8) -0.0004(9) 0.0169(8) C(30) 0.053(1) 0.0290(8) 0.047(1) 0.0032(7) -0.0042(8) 0.0062(7) #------------------------------------------------------------------------------ _computing_data_collection '.' _computing_cell_refinement '.' _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(23) 1.427(2) . . yes O(1) C(25) 1.432(3) . . yes O(2) C(24) 1.424(3) . . yes O(2) C(25) 1.428(3) . . yes C(1) C(2) 1.531(3) . . yes C(1) C(12) 1.614(3) . . yes C(1) C(22) 1.530(3) . . yes C(1) C(23) 1.503(3) . . yes C(2) C(3) 1.353(3) . . yes C(2) C(11) 1.411(3) . . yes C(3) C(4) 1.427(3) . . yes C(4) C(5) 1.418(3) . . yes C(4) C(9) 1.436(3) . . yes C(5) C(6) 1.361(4) . . yes C(6) C(7) 1.401(4) . . yes C(7) C(8) 1.360(4) . . yes C(8) C(9) 1.421(3) . . yes C(9) C(10) 1.417(3) . . yes C(10) C(11) 1.368(3) . . yes C(11) C(12) 1.533(3) . . yes C(12) C(13) 1.535(3) . . yes C(12) C(24) 1.500(3) . . yes C(13) C(14) 1.355(3) . . yes C(13) C(22) 1.414(3) . . yes C(14) C(15) 1.428(3) . . yes C(15) C(16) 1.408(3) . . yes C(15) C(20) 1.436(3) . . yes C(16) C(17) 1.367(3) . . yes C(17) C(18) 1.392(4) . . yes C(18) C(19) 1.363(3) . . yes C(19) C(20) 1.416(3) . . yes C(20) C(21) 1.429(3) . . yes C(21) C(22) 1.355(3) . . yes C(25) C(26) 1.529(4) . . yes C(25) C(30) 1.521(3) . . yes C(26) C(27) 1.526(4) . . yes C(27) C(28) 1.515(4) . . yes C(28) C(29) 1.512(4) . . yes C(29) C(30) 1.525(4) . . yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(23) O(1) C(25) 119.3(2) . 1_555 1_555 yes C(24) O(2) C(25) 118.8(2) . 1_555 1_555 yes C(2) C(1) C(12) 86.5(2) . 1_555 1_555 yes C(2) C(1) C(22) 111.9(2) . 1_555 1_555 yes C(2) C(1) C(23) 121.7(2) . 1_555 1_555 yes C(12) C(1) C(22) 86.5(1) . 1_555 1_555 yes C(12) C(1) C(23) 119.8(2) . 1_555 1_555 yes C(22) C(1) C(23) 120.0(2) . 1_555 1_555 yes C(1) C(2) C(3) 143.3(2) . 1_555 1_555 yes C(1) C(2) C(11) 93.5(2) . 1_555 1_555 yes C(3) C(2) C(11) 123.0(2) . 1_555 1_555 yes C(2) C(3) C(4) 117.3(2) . 1_555 1_555 yes C(3) C(4) C(5) 122.0(2) . 1_555 1_555 yes C(3) C(4) C(9) 120.0(2) . 1_555 1_555 yes C(5) C(4) C(9) 118.0(2) . 1_555 1_555 yes C(4) C(5) C(6) 121.4(2) . 1_555 1_555 yes C(5) C(6) C(7) 120.7(2) . 1_555 1_555 yes C(6) C(7) C(8) 120.1(2) . 1_555 1_555 yes C(7) C(8) C(9) 121.5(2) . 1_555 1_555 yes C(4) C(9) C(8) 118.3(2) . 1_555 1_555 yes C(4) C(9) C(10) 120.5(2) . 1_555 1_555 yes C(8) C(9) C(10) 121.2(2) . 1_555 1_555 yes C(9) C(10) C(11) 117.5(2) . 1_555 1_555 yes C(2) C(11) C(10) 121.8(2) . 1_555 1_555 yes C(2) C(11) C(12) 94.1(2) . 1_555 1_555 yes C(10) C(11) C(12) 144.0(2) . 1_555 1_555 yes C(1) C(12) C(11) 85.9(2) . 1_555 1_555 yes C(1) C(12) C(13) 86.0(1) . 1_555 1_555 yes C(1) C(12) C(24) 120.8(2) . 1_555 1_555 yes C(11) C(12) C(13) 112.1(2) . 1_555 1_555 yes C(11) C(12) C(24) 122.1(2) . 1_555 1_555 yes C(13) C(12) C(24) 119.5(2) . 1_555 1_555 yes C(12) C(13) C(14) 143.5(2) . 1_555 1_555 yes C(12) C(13) C(22) 93.8(2) . 1_555 1_555 yes C(14) C(13) C(22) 122.7(2) . 1_555 1_555 yes C(13) C(14) C(15) 116.8(2) . 1_555 1_555 yes C(14) C(15) C(16) 121.3(2) . 1_555 1_555 yes C(14) C(15) C(20) 120.4(2) . 1_555 1_555 yes C(16) C(15) C(20) 118.3(2) . 1_555 1_555 yes C(15) C(16) C(17) 121.4(2) . 1_555 1_555 yes C(16) C(17) C(18) 120.4(2) . 1_555 1_555 yes C(17) C(18) C(19) 120.4(2) . 1_555 1_555 yes C(18) C(19) C(20) 121.2(2) . 1_555 1_555 yes C(15) C(20) C(19) 118.3(2) . 1_555 1_555 yes C(15) C(20) C(21) 120.5(2) . 1_555 1_555 yes C(19) C(20) C(21) 121.1(2) . 1_555 1_555 yes C(20) C(21) C(22) 116.6(2) . 1_555 1_555 yes C(1) C(22) C(13) 93.7(2) . 1_555 1_555 yes C(1) C(22) C(21) 143.4(2) . 1_555 1_555 yes C(13) C(22) C(21) 122.9(2) . 1_555 1_555 yes O(1) C(23) C(1) 110.9(2) . 1_555 1_555 yes O(2) C(24) C(12) 111.7(2) . 1_555 1_555 yes O(1) C(25) O(2) 112.0(2) . 1_555 1_555 yes O(1) C(25) C(26) 112.4(2) . 1_555 1_555 yes O(1) C(25) C(30) 104.4(2) . 1_555 1_555 yes O(2) C(25) C(26) 113.0(2) . 1_555 1_555 yes O(2) C(25) C(30) 104.1(2) . 1_555 1_555 yes C(26) C(25) C(30) 110.2(2) . 1_555 1_555 yes C(25) C(26) C(27) 111.5(2) . 1_555 1_555 yes C(26) C(27) C(28) 111.5(2) . 1_555 1_555 yes C(27) C(28) C(29) 112.0(2) . 1_555 1_555 yes C(28) C(29) C(30) 110.6(2) . 1_555 1_555 yes C(25) C(30) C(29) 111.9(2) . 1_555 1_555 yes #------------------------------------------------------------------------------ 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 O(1) C(23) C(1) C(2) -50.0(3) 1_555 1_555 1_555 1_555 yes O(1) C(23) C(1) C(12) 55.8(2) 1_555 1_555 1_555 1_555 yes O(1) C(23) C(1) C(22) 160.2(2) 1_555 1_555 1_555 1_555 yes O(1) C(25) O(2) C(24) -73.0(2) 1_555 1_555 1_555 1_555 yes O(1) C(25) C(26) C(27) -61.0(3) 1_555 1_555 1_555 1_555 yes O(1) C(25) C(30) C(29) 64.9(3) 1_555 1_555 1_555 1_555 yes O(2) C(24) C(12) C(1) -56.4(3) 1_555 1_555 1_555 1_555 yes O(2) C(24) C(12) C(11) 49.6(3) 1_555 1_555 1_555 1_555 yes O(2) C(24) C(12) C(13) -160.5(2) 1_555 1_555 1_555 1_555 yes O(2) C(25) O(1) C(23) 74.5(2) 1_555 1_555 1_555 1_555 yes O(2) C(25) C(26) C(27) 171.0(2) 1_555 1_555 1_555 1_555 yes O(2) C(25) C(30) C(29) -177.5(2) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(4) -173.2(2) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(11) C(10) 177.0(2) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(11) C(12) 0.0(2) 1_555 1_555 1_555 1_555 yes C(1) C(12) C(11) C(2) 0.0(2) 1_555 1_555 1_555 1_555 yes C(1) C(12) C(11) C(10) -175.7(3) 1_555 1_555 1_555 1_555 yes C(1) C(12) C(13) C(14) 180.0(3) 1_555 1_555 1_555 1_555 yes C(1) C(12) C(13) C(22) 0.4(2) 1_555 1_555 1_555 1_555 yes C(1) C(22) C(13) C(12) -0.4(2) 1_555 1_555 1_555 1_555 yes C(1) C(22) C(13) C(14) 179.9(2) 1_555 1_555 1_555 1_555 yes C(1) C(22) C(21) C(20) 179.1(3) 1_555 1_555 1_555 1_555 yes C(1) C(23) O(1) C(25) -82.6(2) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(12) C(11) 0.0(1) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(12) C(13) -112.6(2) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(12) C(24) 125.2(2) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(22) C(13) 85.2(2) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(22) C(21) -93.8(4) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(4) C(5) 177.6(2) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(4) C(9) -1.1(3) 1_555 1_555 1_555 1_555 yes C(2) C(11) C(10) C(9) -1.7(3) 1_555 1_555 1_555 1_555 yes C(2) C(11) C(12) C(13) 84.0(2) 1_555 1_555 1_555 1_555 yes C(2) C(11) C(12) C(24) -124.1(2) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(1) C(12) 175.0(3) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(1) C(22) 90.2(3) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(1) C(23) -61.8(4) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(11) C(10) 0.6(3) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(11) C(12) -176.4(2) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(5) C(6) -178.7(2) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(9) C(8) 178.8(2) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(9) C(10) 0.1(3) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(2) C(11) 0.8(3) 1_555 1_555 1_555 1_555 yes C(4) C(5) C(6) C(7) 0.0(4) 1_555 1_555 1_555 1_555 yes C(4) C(9) C(8) C(7) -0.1(3) 1_555 1_555 1_555 1_555 yes C(4) C(9) C(10) C(11) 1.3(3) 1_555 1_555 1_555 1_555 yes C(5) C(4) C(9) C(8) 0.0(3) 1_555 1_555 1_555 1_555 yes C(5) C(4) C(9) C(10) -178.7(2) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(7) C(8) -0.1(4) 1_555 1_555 1_555 1_555 yes C(6) C(5) C(4) C(9) 0.0(3) 1_555 1_555 1_555 1_555 yes C(6) C(7) C(8) C(9) 0.2(4) 1_555 1_555 1_555 1_555 yes C(7) C(8) C(9) C(10) 178.6(2) 1_555 1_555 1_555 1_555 yes C(8) C(9) C(10) C(11) -177.4(2) 1_555 1_555 1_555 1_555 yes C(9) C(10) C(11) C(12) 173.4(3) 1_555 1_555 1_555 1_555 yes C(10) C(11) C(12) C(13) -91.7(3) 1_555 1_555 1_555 1_555 yes C(10) C(11) C(12) C(24) 60.2(4) 1_555 1_555 1_555 1_555 yes C(11) C(2) C(1) C(12) 0.0(2) 1_555 1_555 1_555 1_555 yes C(11) C(2) C(1) C(22) -84.7(2) 1_555 1_555 1_555 1_555 yes C(11) C(2) C(1) C(23) 123.3(2) 1_555 1_555 1_555 1_555 yes C(11) C(12) C(1) C(22) 112.2(2) 1_555 1_555 1_555 1_555 yes C(11) C(12) C(1) C(23) -124.9(2) 1_555 1_555 1_555 1_555 yes C(11) C(12) C(13) C(14) 96.1(4) 1_555 1_555 1_555 1_555 yes C(11) C(12) C(13) C(22) -83.5(2) 1_555 1_555 1_555 1_555 yes C(12) C(1) C(22) C(13) 0.4(2) 1_555 1_555 1_555 1_555 yes C(12) C(1) C(22) C(21) -178.6(3) 1_555 1_555 1_555 1_555 yes C(12) C(13) C(14) C(15) -178.6(3) 1_555 1_555 1_555 1_555 yes C(12) C(13) C(22) C(21) 178.9(2) 1_555 1_555 1_555 1_555 yes C(12) C(24) O(2) C(25) 81.1(3) 1_555 1_555 1_555 1_555 yes C(13) C(12) C(1) C(22) -0.4(2) 1_555 1_555 1_555 1_555 yes C(13) C(12) C(1) C(23) 122.5(2) 1_555 1_555 1_555 1_555 yes C(13) C(14) C(15) C(16) 177.8(2) 1_555 1_555 1_555 1_555 yes C(13) C(14) C(15) C(20) -0.5(3) 1_555 1_555 1_555 1_555 yes C(13) C(22) C(1) C(23) -122.3(2) 1_555 1_555 1_555 1_555 yes C(13) C(22) C(21) C(20) 0.3(3) 1_555 1_555 1_555 1_555 yes C(14) C(13) C(12) C(24) -56.7(4) 1_555 1_555 1_555 1_555 yes C(14) C(13) C(22) C(21) -0.9(4) 1_555 1_555 1_555 1_555 yes C(14) C(15) C(16) C(17) -177.8(2) 1_555 1_555 1_555 1_555 yes C(14) C(15) C(20) C(19) 179.6(2) 1_555 1_555 1_555 1_555 yes C(14) C(15) C(20) C(21) 0.1(3) 1_555 1_555 1_555 1_555 yes C(15) C(14) C(13) C(22) 0.9(3) 1_555 1_555 1_555 1_555 yes C(15) C(16) C(17) C(18) -1.3(4) 1_555 1_555 1_555 1_555 yes C(15) C(20) C(19) C(18) -2.4(4) 1_555 1_555 1_555 1_555 yes C(15) C(20) C(21) C(22) 0.0(3) 1_555 1_555 1_555 1_555 yes C(16) C(15) C(20) C(19) 1.3(3) 1_555 1_555 1_555 1_555 yes C(16) C(15) C(20) C(21) -178.3(2) 1_555 1_555 1_555 1_555 yes C(16) C(17) C(18) C(19) 0.3(5) 1_555 1_555 1_555 1_555 yes C(17) C(16) C(15) C(20) 0.5(4) 1_555 1_555 1_555 1_555 yes C(17) C(18) C(19) C(20) 1.6(4) 1_555 1_555 1_555 1_555 yes C(18) C(19) C(20) C(21) 177.2(2) 1_555 1_555 1_555 1_555 yes C(19) C(20) C(21) C(22) -179.5(2) 1_555 1_555 1_555 1_555 yes C(21) C(22) C(1) C(23) 58.7(4) 1_555 1_555 1_555 1_555 yes C(22) C(1) C(12) C(24) -122.5(2) 1_555 1_555 1_555 1_555 yes C(22) C(13) C(12) C(24) 123.7(2) 1_555 1_555 1_555 1_555 yes C(23) O(1) C(25) C(26) -54.1(2) 1_555 1_555 1_555 1_555 yes C(23) O(1) C(25) C(30) -173.5(2) 1_555 1_555 1_555 1_555 yes C(23) C(1) C(12) C(24) 0.3(3) 1_555 1_555 1_555 1_555 yes C(24) O(2) C(25) C(26) 55.2(3) 1_555 1_555 1_555 1_555 yes C(24) O(2) C(25) C(30) 174.8(2) 1_555 1_555 1_555 1_555 yes C(25) C(26) C(27) C(28) -54.6(3) 1_555 1_555 1_555 1_555 yes C(25) C(30) C(29) C(28) 56.2(3) 1_555 1_555 1_555 1_555 yes C(26) C(25) C(30) C(29) -56.0(3) 1_555 1_555 1_555 1_555 yes C(26) C(27) C(28) C(29) 54.7(3) 1_555 1_555 1_555 1_555 yes C(27) C(26) C(25) C(30) 54.9(3) 1_555 1_555 1_555 1_555 yes C(27) C(28) C(29) C(30) -55.1(3) 1_555 1_555 1_555 1_555 yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(1) C(5) 3.433(3) . 3_666 ? O(2) C(8) 3.462(3) . 3_566 ? C(6) C(21) 3.526(3) . 4_555 ? C(10) C(16) 3.579(3) . 3_556 ? C(15) C(28) 3.597(4) . 4_555 ? C(20) C(28) 3.496(4) . 4_555 ? #------------------------------------------------------------------------------