# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 1145 _publ_requested_journal 'Journal of Materials Chemistry' loop_ _publ_author_name 'Bertini, Fabio' 'Botta, Chiara' 'Destri, Silvia' 'Marchio, Luciano' 'Pasini, Mariacecilia' 'Porzio, W.' _publ_contact_author_name 'Dr W Porzio' _publ_contact_author_address ; Dr W Porzio Istituto di Chimica delle Macromolecole de CNR via E Bassini 15 Milano 20133 ITALY ; _publ_contact_author_email 'RX@ICM.MI.CNR.IT' _publ_section_title ; Synthesis and crystal structure and optical properties of fluorenic-core oligomers ; data_2,7-dibromo-9,9-cyclopentanefluorene #(4) _database_code_CSD 158135 _chemical_name_common ? _chemical_formula_moiety 2,7-dibromo-9,9-cyclopentanefluorene _chemical_formula_sum 'C17 H14 Br2' _chemical_formula_weight 378.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 11.746(4) _cell_length_b 11.892(3) _cell_length_c 20.568(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2873.0(16) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 18.3 _cell_measurement_theta_max 35.9 _exptl_crystal_description 'prism' _exptl_crystal_colour 'white' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.748 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 7.000 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.860 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4 diffractometer' _diffrn_measurement_method theta/2-theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 'every 100 reflections' _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 2718 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0546 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 4.30 _diffrn_reflns_theta_max 69.94 _reflns_number_total 2718 _reflns_number_gt 1617 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Enraf-Nonius CAD4 local programs' _computing_cell_refinement 'local programs' _computing_data_reduction 'local programs' _computing_structure_solution 'SIR-92' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP, PLUTON' _computing_publication_material 'SHELXL-97' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0276P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2718 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0704 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0758 _refine_ls_wR_factor_gt 0.0651 _refine_ls_goodness_of_fit_ref 0.837 _refine_ls_restrained_S_all 0.837 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.10765(4) -0.08486(5) 0.92559(2) 0.06186(16) Uani 1 d . . . Br2 Br 0.56513(5) 0.27214(5) 0.53387(3) 0.07112(18) Uani 1 d . . . C1 C 0.4137(3) 0.1474(3) 0.61340(19) 0.0455(10) Uani 1 d . . . H1 H 0.3863 0.1187 0.5744 0.047(11) Uiso 1 calc R . . C2 C 0.5015(4) 0.2252(4) 0.6143(2) 0.0482(10) Uani 1 d . . . C3 C 0.5450(4) 0.2699(4) 0.6714(2) 0.0545(11) Uani 1 d . . . H3 H 0.6044 0.3215 0.6703 0.092(18) Uiso 1 calc R . . C4 C 0.4985(4) 0.2363(4) 0.7296(2) 0.0522(11) Uani 1 d . . . H4 H 0.5260 0.2657 0.7684 0.053(12) Uiso 1 calc R . . C5 C 0.3579(4) 0.1241(4) 0.85165(19) 0.0514(12) Uani 1 d . . . H5 H 0.4121 0.1732 0.8683 0.071(15) Uiso 1 calc R . . C6 C 0.2860(4) 0.0655(4) 0.89303(19) 0.0548(12) Uani 1 d . . . H6 H 0.2921 0.0746 0.9378 0.043(11) Uiso 1 calc R . . C7 C 0.2052(3) -0.0064(4) 0.86745(19) 0.0467(11) Uani 1 d . . . C8 C 0.1935(4) -0.0241(4) 0.80133(19) 0.0461(10) Uani 1 d . . . H8 H 0.1392 -0.0736 0.7851 0.045(12) Uiso 1 calc R . . C9 C 0.2715(3) 0.0303(3) 0.68600(17) 0.0383(9) Uani 1 d . . . C10 C 0.3681(3) 0.1136(3) 0.67231(18) 0.0385(9) Uani 1 d . . . C11 C 0.4103(3) 0.1582(3) 0.73043(18) 0.0426(10) Uani 1 d . . . C12 C 0.3481(4) 0.1084(3) 0.78491(18) 0.0434(10) Uani 1 d . . . C13 C 0.2657(3) 0.0346(3) 0.75988(17) 0.0395(9) Uani 1 d . . . C14 C 0.2944(4) -0.0886(3) 0.65842(18) 0.0461(10) Uani 1 d . . . H14A H 0.3749 -0.1066 0.6606 0.075(16) Uiso 1 calc R . . H14B H 0.2523 -0.1449 0.6826 0.043(11) Uiso 1 calc R . . C15 C 0.2539(4) -0.0841(4) 0.58757(18) 0.0533(11) Uani 1 d . . . H15A H 0.3172 -0.0682 0.5587 0.13(2) Uiso 1 calc R . . H15B H 0.2202 -0.1553 0.5750 0.059(13) Uiso 1 calc R . . C16 C 0.1654(4) 0.0102(4) 0.5842(2) 0.0660(14) Uani 1 d . . . H16A H 0.1879 0.0661 0.5523 0.11(2) Uiso 1 calc R . . H16B H 0.0918 -0.0198 0.5717 0.079(17) Uiso 1 calc R . . C17 C 0.1589(4) 0.0629(4) 0.65183(19) 0.0487(11) Uani 1 d . . . H17A H 0.0941 0.0337 0.6757 0.048(12) Uiso 1 calc R . . H17B H 0.1519 0.1440 0.6487 0.057(13) Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0666(3) 0.0741(3) 0.0449(2) 0.0049(3) 0.0104(2) -0.0024(3) Br2 0.0764(4) 0.0719(4) 0.0650(3) 0.0101(3) 0.0166(3) -0.0190(3) C1 0.052(3) 0.043(2) 0.041(2) -0.0029(19) -0.001(2) -0.004(2) C2 0.051(3) 0.044(2) 0.050(2) 0.008(2) 0.004(2) 0.000(2) C3 0.047(3) 0.046(3) 0.071(3) 0.000(2) -0.002(2) -0.011(2) C4 0.051(3) 0.053(3) 0.053(3) -0.008(2) -0.009(2) -0.003(2) C5 0.052(3) 0.060(3) 0.042(2) -0.010(2) -0.006(2) -0.006(2) C6 0.065(3) 0.069(3) 0.031(2) -0.005(2) 0.000(2) 0.006(3) C7 0.046(3) 0.055(3) 0.039(2) 0.000(2) 0.0070(19) 0.003(2) C8 0.048(3) 0.047(3) 0.043(2) -0.002(2) -0.001(2) -0.001(2) C9 0.041(2) 0.040(2) 0.035(2) -0.0024(18) -0.0041(17) 0.002(2) C10 0.039(2) 0.033(2) 0.043(2) 0.0016(18) -0.0046(18) -0.0006(18) C11 0.043(3) 0.043(2) 0.041(2) -0.0025(18) -0.0070(19) 0.001(2) C12 0.044(2) 0.046(3) 0.040(2) -0.0029(19) -0.0013(19) 0.003(2) C13 0.043(2) 0.043(2) 0.0327(19) -0.0014(18) 0.0040(18) 0.004(2) C14 0.056(3) 0.038(2) 0.044(2) -0.002(2) 0.003(2) 0.001(2) C15 0.071(3) 0.050(3) 0.040(2) -0.009(2) 0.000(2) -0.013(3) C16 0.074(4) 0.071(3) 0.054(3) -0.001(3) -0.018(3) -0.005(3) C17 0.041(2) 0.056(3) 0.050(3) 0.005(2) -0.004(2) 0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C7 1.901(4) . ? Br2 C2 1.900(4) . ? C1 C10 1.385(5) . ? C1 C2 1.385(5) . ? C2 C3 1.386(6) . ? C3 C4 1.376(5) . ? C4 C11 1.391(5) . ? C5 C12 1.390(5) . ? C5 C6 1.387(5) . ? C6 C7 1.381(5) . ? C7 C8 1.383(5) . ? C8 C13 1.390(5) . ? C9 C13 1.522(5) . ? C9 C10 1.532(5) . ? C9 C14 1.548(5) . ? C9 C17 1.547(5) . ? C10 C11 1.399(5) . ? C11 C12 1.463(5) . ? C12 C13 1.404(5) . ? C14 C15 1.534(5) . ? C15 C16 1.532(6) . ? C16 C17 1.528(5) . ? 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 C10 C1 C2 118.0(4) . . ? C3 C2 C1 122.8(4) . . ? C3 C2 Br2 118.7(3) . . ? C1 C2 Br2 118.5(3) . . ? C4 C3 C2 118.7(4) . . ? C3 C4 C11 120.0(4) . . ? C12 C5 C6 119.2(4) . . ? C7 C6 C5 119.7(4) . . ? C8 C7 C6 122.5(4) . . ? C8 C7 Br1 119.0(3) . . ? C6 C7 Br1 118.6(3) . . ? C7 C8 C13 117.8(4) . . ? C13 C9 C10 101.3(3) . . ? C13 C9 C14 113.8(3) . . ? C10 C9 C14 113.3(3) . . ? C13 C9 C17 114.0(3) . . ? C10 C9 C17 112.8(3) . . ? C14 C9 C17 102.2(3) . . ? C1 C10 C11 120.0(4) . . ? C1 C10 C9 129.4(4) . . ? C11 C10 C9 110.5(3) . . ? C4 C11 C10 120.5(4) . . ? C4 C11 C12 130.7(4) . . ? C10 C11 C12 108.9(3) . . ? C5 C12 C13 120.2(4) . . ? C5 C12 C11 131.3(4) . . ? C13 C12 C11 108.5(3) . . ? C8 C13 C12 120.6(3) . . ? C8 C13 C9 128.6(4) . . ? C12 C13 C9 110.8(3) . . ? C15 C14 C9 105.2(3) . . ? C16 C15 C14 106.2(3) . . ? C17 C16 C15 107.0(4) . . ? C16 C17 C9 105.6(4) . . ? _diffrn_measured_fraction_theta_max 0.885 _diffrn_reflns_theta_full 69.94 _diffrn_measured_fraction_theta_full 0.885 _refine_diff_density_max 0.329 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.066 #=END data_tftc6no _database_code_CSD 158136 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H38 S2' _chemical_formula_weight 498.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'tetragonal' _symmetry_space_group_name_H-M 'I41/a ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 16.5630(10) _cell_length_b 16.5630(10) _cell_length_c 20.6570(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5666.9(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1024 _cell_measurement_theta_min 1.58 _cell_measurement_theta_max 23.27 _exptl_crystal_description prism _exptl_crystal_colour white _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2144 _exptl_absorpt_coefficient_mu 0.207 _exptl_absorpt_correction_type 'SADABS' _exptl_absorpt_correction_T_min 0.980 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'theta dependent correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART CCD diffractometer' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7477 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.3801 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 23.27 _reflns_number_total 2051 _reflns_number_gt 967 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0250P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2051 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0786 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.0944 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 0.728 _refine_ls_restrained_S_all 0.728 _refine_ls_shift/su_max 0.118 _refine_ls_shift/su_mean 0.050 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 S S 0.62844(7) 0.55833(6) 0.10626(4) 0.0966(4) Uani 1 1 d . . . C1 C 0.58795(17) 0.44047(18) 0.19506(14) 0.0484(8) Uani 1 1 d . . . C2 C 0.56275(16) 0.38886(19) 0.14443(13) 0.0470(8) Uani 1 1 d . . . H2 H 0.5684 0.4054 0.1016 0.056 Uiso 1 1 calc R . . C3 C 0.52992(16) 0.31426(19) 0.15800(12) 0.0440(8) Uani 1 1 d . . . C4 C 0.51963(17) 0.28961(16) 0.22239(13) 0.0462(8) Uani 1 1 d . . . C5 C 0.54465(18) 0.3394(2) 0.27250(14) 0.0593(9) Uani 1 1 d . . . H5 H 0.5386 0.3230 0.3153 0.071 Uiso 1 1 calc R . . C6 C 0.57850(18) 0.41326(19) 0.25850(14) 0.0587(9) Uani 1 1 d . . . H6 H 0.5956 0.4460 0.2924 0.070 Uiso 1 1 calc R . . C7 C 0.62287(17) 0.52033(19) 0.18201(14) 0.0500(8) Uani 1 1 d . . . C8 C 0.6545(2) 0.5733(2) 0.22565(16) 0.0738(11) Uani 1 1 d . . . H8 H 0.6579 0.5635 0.2699 0.089 Uiso 1 1 calc R . . C9 C 0.6812(2) 0.6443(2) 0.19568(18) 0.0888(13) Uani 1 1 d . . . H9 H 0.7038 0.6871 0.2185 0.107 Uiso 1 1 calc R . . C10 C 0.6716(2) 0.6452(2) 0.13205(18) 0.0859(12) Uani 1 1 d . . . H10 H 0.6866 0.6877 0.1052 0.103 Uiso 1 1 calc R . . C11 C 0.5000 0.2500 0.11121(18) 0.0440(11) Uani 1 2 d S . . C12 C 0.43220(19) 0.2823(2) 0.06719(14) 0.0489(9) Uani 1 1 d . . . H12A H 0.4551(15) 0.3233(15) 0.0391(11) 0.059 Uiso 1 1 calc . . . H12B H 0.4139(14) 0.2384(16) 0.0398(11) 0.059 Uiso 1 1 calc . . . C13 C 0.3592(2) 0.3182(2) 0.10079(15) 0.0562(9) Uani 1 1 d . . . H13A H 0.3765(16) 0.3621(16) 0.1286(13) 0.067 Uiso 1 1 calc . . . H13B H 0.3343(16) 0.2774(16) 0.1279(13) 0.067 Uiso 1 1 calc . . . C14 C 0.2974(2) 0.3497(2) 0.05287(15) 0.0571(10) Uani 1 1 d . . . H14A H 0.3235(16) 0.3895(16) 0.0255(13) 0.069 Uiso 1 1 calc . . . H14B H 0.2810(16) 0.3053(16) 0.0253(13) 0.069 Uiso 1 1 calc . . . C15 C 0.2226(2) 0.3873(2) 0.08114(15) 0.0569(10) Uani 1 1 d . . . H15A H 0.2381(16) 0.4315(15) 0.1093(13) 0.068 Uiso 1 1 calc . . . H15B H 0.1946(16) 0.3474(16) 0.1072(12) 0.068 Uiso 1 1 calc . . . C16 C 0.1655(2) 0.4189(2) 0.02946(18) 0.0694(11) Uani 1 1 d . . . H16A H 0.1935(17) 0.4594(17) 0.0040(13) 0.083 Uiso 1 1 calc . . . H16B H 0.1514(18) 0.3748(17) 0.0007(13) 0.083 Uiso 1 1 calc . . . C17 C 0.0902(2) 0.4548(2) 0.05574(17) 0.0960(13) Uani 1 1 d . . . H17A H 0.0570 0.4734 0.0207 0.144 Uiso 1 1 calc R . . H17B H 0.1035 0.4994 0.0834 0.144 Uiso 1 1 calc R . . H17C H 0.0613 0.4148 0.0801 0.144 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S 0.1327(10) 0.0960(8) 0.0612(6) 0.0013(6) -0.0020(6) -0.0472(7) C1 0.042(2) 0.060(2) 0.0433(19) -0.0071(17) 0.0048(15) 0.0045(18) C2 0.046(2) 0.057(2) 0.0384(18) -0.0009(17) 0.0017(16) 0.0032(17) C3 0.0402(19) 0.052(2) 0.0398(19) -0.0021(15) -0.0003(14) 0.0024(16) C4 0.044(2) 0.053(2) 0.0413(16) 0.0003(15) -0.0001(15) 0.0062(16) C5 0.073(3) 0.071(3) 0.0345(18) -0.0021(18) -0.0002(17) -0.001(2) C6 0.066(2) 0.063(2) 0.047(2) -0.0131(18) -0.0025(17) -0.003(2) C7 0.044(2) 0.055(2) 0.0512(19) -0.0065(18) 0.0050(16) -0.0005(17) C8 0.108(3) 0.058(2) 0.056(2) -0.010(2) 0.004(2) -0.020(2) C9 0.121(4) 0.076(3) 0.070(3) -0.027(2) 0.000(2) -0.024(3) C10 0.112(3) 0.069(3) 0.077(3) -0.006(2) 0.003(2) -0.038(2) C11 0.046(3) 0.050(3) 0.036(2) 0.000 0.000 -0.001(2) C12 0.055(2) 0.054(2) 0.0372(18) 0.0005(16) -0.0005(17) 0.0015(18) C13 0.061(2) 0.063(2) 0.0445(19) 0.0076(18) -0.0074(18) -0.0016(19) C14 0.063(3) 0.059(3) 0.049(2) 0.0043(17) -0.0085(19) 0.001(2) C15 0.056(2) 0.060(2) 0.055(2) 0.0076(18) -0.0093(19) 0.006(2) C16 0.065(3) 0.069(3) 0.075(3) 0.010(2) -0.015(2) 0.008(2) C17 0.073(3) 0.112(3) 0.103(3) 0.021(2) -0.015(2) 0.024(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S C7 1.689(3) . ? S C10 1.692(3) . ? C1 C6 1.395(4) . ? C1 C2 1.414(4) . ? C1 C7 1.469(4) . ? C2 C3 1.379(3) . ? C3 C4 1.402(3) . ? C3 C11 1.521(3) . ? C4 C5 1.387(3) . ? C4 C4 1.464(5) 6_554 ? C5 C6 1.376(4) . ? C7 C8 1.363(4) . ? C8 C9 1.401(4) . ? C9 C10 1.324(4) . ? C11 C3 1.521(3) 6_554 ? C11 C12 1.541(4) 6_554 ? C11 C12 1.541(4) . ? C12 C13 1.516(4) . ? C13 C14 1.516(4) . ? C14 C15 1.504(4) . ? C15 C16 1.519(4) . ? C16 C17 1.485(5) . ? 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 C7 S C10 92.76(17) . . ? C6 C1 C2 117.8(3) . . ? C6 C1 C7 120.5(3) . . ? C2 C1 C7 121.7(3) . . ? C3 C2 C1 120.5(3) . . ? C2 C3 C4 120.1(3) . . ? C2 C3 C11 128.8(3) . . ? C4 C3 C11 111.1(3) . . ? C5 C4 C3 119.9(3) . . ? C5 C4 C4 131.74(18) . 6_554 ? C3 C4 C4 108.36(17) . 6_554 ? C6 C5 C4 119.6(3) . . ? C5 C6 C1 122.0(3) . . ? C8 C7 C1 127.6(3) . . ? C8 C7 S 110.6(2) . . ? C1 C7 S 121.8(2) . . ? C7 C8 C9 111.7(3) . . ? C10 C9 C8 114.2(3) . . ? C9 C10 S 110.7(3) . . ? C3 C11 C3 101.1(3) . 6_554 ? C3 C11 C12 112.38(16) . 6_554 ? C3 C11 C12 111.68(16) 6_554 6_554 ? C3 C11 C12 111.68(16) . . ? C3 C11 C12 112.38(16) 6_554 . ? C12 C11 C12 107.7(3) 6_554 . ? C13 C12 C11 116.6(2) . . ? C12 C13 C14 112.0(3) . . ? C15 C14 C13 116.4(3) . . ? C14 C15 C16 112.5(3) . . ? C17 C16 C15 113.8(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.172 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.032 data_FT2 _database_code_CSD 158137 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C25 H20 S2' _chemical_formula_weight 384.13 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pca21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 12.666(4) _cell_length_b 21.383(9) _cell_length_c 7.3510(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1990.9(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8.7 _cell_measurement_theta_max 12.7 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.267 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius Cad4' _diffrn_measurement_method 'omega-2theta' _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 100 _diffrn_standards_decay_% 'no decay' _diffrn_reflns_number 2343 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0732 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 26.96 _reflns_number_total 2343 _reflns_number_observed 1232 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0991P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.15(24) _refine_ls_number_reflns 2343 _refine_ls_number_parameters 209 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1655 _refine_ls_R_factor_gt 0.0609 _refine_ls_wR_factor_all 0.1924 _refine_ls_wR_factor_ref 0.1607 _refine_ls_goodness_of_fit_all 1.146 _refine_ls_goodness_of_fit_obs 1.376 _refine_ls_restrained_S_all 1.144 _refine_ls_restrained_S_obs 1.373 _refine_ls_shift/su_max 0.001 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.9692(2) 0.50049(12) 0.2654(3) 0.0742(10) Uani 0.778(13) d P . C3' C 0.9692(2) 0.50049(12) 0.2654(3) 0.0742(10) Uani 0.22(2) d P . S2 S 0.9695(2) -0.02395(11) 0.2068(4) 0.0753(13) Uani 0.609(13) d P . C18' C 0.9695(2) -0.02395(11) 0.2068(4) 0.0753(13) Uani 0.39(2) d P . C1 C 0.9117(7) 0.5702(3) 0.2571(12) 0.088(2) Uani 1 d . . C2 C 0.8240(6) 0.5725(3) 0.1600(11) 0.078(2) Uani 1 d . . C3 C 0.7890(4) 0.5122(2) 0.0725(8) 0.086(3) Uani 0.80(2) d P . S1' S 0.7890(4) 0.5122(2) 0.0725(8) 0.086(3) Uani 0.200(14) d P . C4 C 0.8758(5) 0.4666(3) 0.1289(8) 0.057(2) Uani 1 d . . C5 C 0.8793(4) 0.4008(3) 0.0794(8) 0.0500(14) Uiso 1 d . . C6 C 0.8255(5) 0.3808(3) -0.0763(9) 0.058(2) Uiso 1 d . . H6 H 0.7909(5) 0.4100(3) -0.1484(9) 0.074(19) Uiso 1 calc R . C7 C 0.8229(4) 0.3189(2) -0.1246(9) 0.0547(15) Uiso 1 d . . H7 H 0.7870(4) 0.3063(2) -0.2286(9) 0.085(22) Uiso 1 calc R . C8 C 0.8742(5) 0.2754(2) -0.0170(8) 0.0479(14) Uiso 1 d . . C9 C 0.9329(4) 0.2952(2) 0.1364(8) 0.0465(13) Uiso 1 d . . C10 C 0.9345(5) 0.3567(2) 0.1831(9) 0.0504(14) Uiso 1 d . . H10 H 0.9725(5) 0.3696(2) 0.2847(9) 0.094(24) Uiso 1 calc R . C11 C 0.8740(4) 0.2068(3) -0.0232(8) 0.0481(13) Uiso 1 d . . C12 C 0.8201(4) 0.1660(3) -0.1379(9) 0.0538(15) Uiso 1 d . . H12 H 0.7830(4) 0.1810(3) -0.2378(9) 0.085(21) Uiso 1 calc R . C13 C 0.8228(4) 0.1036(3) -0.1009(9) 0.056(2) Uiso 1 d . . H13 H 0.7864(4) 0.0763(3) -0.1767(9) 0.083(21) Uiso 1 calc R . C14 C 0.8792(4) 0.0789(3) 0.0489(8) 0.0510(15) Uiso 1 d . . C15 C 0.9345(5) 0.1207(2) 0.1609(9) 0.0525(15) Uiso 1 d . . H15 H 0.9729(5) 0.1057(2) 0.2595(9) 0.075(19) Uiso 1 calc R . C16 C 0.9320(4) 0.1838(2) 0.1249(8) 0.0462(13) Uiso 1 d . . C17 C 0.8754(5) 0.0112(3) 0.0894(8) 0.055(2) Uani 1 d . . C18 C 0.7827(3) -0.0338(2) 0.0218(6) 0.083(2) Uani 0.65(2) d P . S2' S 0.7827(3) -0.0338(2) 0.0218(6) 0.083(2) Uani 0.346(13) d P . C19 C 0.8248(6) -0.0958(4) 0.1048(12) 0.082(2) Uani 1 d . . C20 C 0.9163(6) -0.0933(3) 0.1961(12) 0.077(2) Uani 1 d . . C21 C 0.9796(4) 0.2374(3) 0.2325(8) 0.0453(13) Uani 1 d . . C22 C 1.1025(5) 0.2369(4) 0.2245(13) 0.074(2) Uani 1 d . . H22A H 1.1297(5) 0.1946(4) 0.2339(13) 0.088(23) Uiso 1 calc R . H22B H 1.1278(5) 0.2555(4) 0.1125(13) 0.125(38) Uiso 1 calc R . C23 C 1.1349(7) 0.2763(5) 0.3902(15) 0.097(3) Uani 1 d . . H23A H 1.2022(7) 0.2621(5) 0.4378(15) 0.223(65) Uiso 1 calc R . H23B H 1.1411(7) 0.3200(5) 0.3569(15) 0.233(66) Uiso 1 calc R . C24 C 1.0491(8) 0.2675(4) 0.5298(11) 0.093(3) Uani 1 d . . H24A H 1.0279(8) 0.3077(4) 0.5786(11) 0.181(51) Uiso 1 calc R . H24B H 1.0748(8) 0.2419(4) 0.6293(11) 0.238(76) Uiso 1 calc R . C25 C 0.9564(5) 0.2361(3) 0.4395(8) 0.061(2) Uani 1 d . . H25A H 0.8916(5) 0.2585(3) 0.4662(8) 0.094(27) Uiso 1 calc R . H25B H 0.9492(5) 0.1934(3) 0.4820(8) 0.120(32) Uiso 1 calc R . HC1 H 0.9560(5) 0.6059(3) 0.3069(8) 0.113(28) Uiso 1 d R . HC2 H 0.7698(5) 0.6105(3) 0.1297(8) 0.102(24) Uiso 1 d R . HC19 H 0.7841(5) -0.1387(3) 0.1282(8) 0.394(107) Uiso 1 d R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.076(2) 0.0752(15) 0.071(2) -0.0047(12) -0.0211(13) -0.0082(12) C3' 0.076(2) 0.0752(15) 0.071(2) -0.0047(12) -0.0211(13) -0.0082(12) S2 0.088(2) 0.065(2) 0.072(2) 0.0058(13) -0.015(2) 0.0127(12) C18' 0.088(2) 0.065(2) 0.072(2) 0.0058(13) -0.015(2) 0.0127(12) C1 0.103(6) 0.080(5) 0.080(6) -0.004(5) -0.007(5) -0.032(5) C2 0.096(5) 0.065(4) 0.074(5) 0.018(4) -0.012(5) -0.003(4) C3 0.098(5) 0.076(4) 0.086(4) 0.009(3) 0.016(3) -0.006(2) S1' 0.098(5) 0.076(4) 0.086(4) 0.009(3) 0.016(3) -0.006(2) C4 0.049(4) 0.079(4) 0.043(3) 0.014(3) -0.001(3) -0.006(3) C17 0.060(4) 0.069(4) 0.035(3) -0.014(3) 0.004(3) 0.003(3) C18 0.095(4) 0.079(3) 0.074(3) -0.005(2) -0.008(2) -0.003(2) S2' 0.095(4) 0.079(3) 0.074(3) -0.005(2) -0.008(2) -0.003(2) C19 0.095(6) 0.077(5) 0.075(5) -0.008(4) 0.004(5) -0.011(4) C20 0.086(5) 0.076(4) 0.070(5) -0.006(4) 0.006(5) 0.003(4) C21 0.037(3) 0.065(3) 0.034(3) 0.002(2) -0.009(3) 0.000(2) C22 0.044(3) 0.090(5) 0.088(6) -0.009(5) -0.015(4) 0.001(3) C23 0.068(5) 0.111(7) 0.112(8) -0.012(6) -0.040(6) 0.003(4) C24 0.134(8) 0.091(6) 0.054(5) -0.002(4) -0.037(6) -0.025(5) C25 0.075(5) 0.070(4) 0.038(3) 0.000(3) -0.013(3) 0.008(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.660(9) . ? S1 C4 1.712(6) . ? C3' C1 1.660(9) . ? C3' C4 1.712(6) . ? S2 C20 1.631(8) . ? S2 C17 1.652(7) . ? C18' C20 1.631(8) . ? C18' C17 1.652(7) . ? C1 C2 1.321(11) . ? C2 S1' 1.507(9) . ? C2 C3 1.507(9) . ? C3 C4 1.527(7) . ? S1' C4 1.527(7) . ? C4 C5 1.454(8) . ? C5 C10 1.399(8) . ? C5 C6 1.400(9) . ? C6 C7 1.370(8) . ? C7 C8 1.383(8) . ? C8 C9 1.415(8) . ? C8 C11 1.468(8) . ? C9 C10 1.360(7) . ? C9 C21 1.541(8) . ? C11 C12 1.392(8) . ? C11 C16 1.402(8) . ? C12 C13 1.361(8) . ? C13 C14 1.415(8) . ? C14 C15 1.402(8) . ? C14 C17 1.479(8) . ? C15 C16 1.377(7) . ? C16 C21 1.517(8) . ? C17 S2' 1.596(7) . ? C17 C18 1.596(7) . ? C18 C19 1.554(9) . ? S2' C19 1.554(9) . ? C19 C20 1.341(11) . ? C21 C25 1.550(9) . ? C21 C22 1.558(8) . ? C22 C23 1.536(12) . ? C23 C24 1.507(13) . ? C24 C25 1.507(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 S1 C4 93.2(4) . . ? C1 C3' C4 93.2(4) . . ? C20 S2 C17 95.2(4) . . ? C20 C18' C17 95.2(4) . . ? C2 C1 S1 114.9(6) . . ? C2 C1 C3' 114.9(6) . . ? S1 C1 C3' 0.0(2) . . ? C1 C2 S1' 116.5(6) . . ? C1 C2 C3 116.5(6) . . ? S1' C2 C3 0.0(6) . . ? C2 C3 C4 102.6(5) . . ? C2 S1' C4 102.6(5) . . ? C5 C4 S1' 125.0(5) . . ? C5 C4 C3 125.0(5) . . ? S1' C4 C3 0.0(6) . . ? C5 C4 S1 122.3(5) . . ? S1' C4 S1 112.7(4) . . ? C3 C4 S1 112.7(4) . . ? C5 C4 C3' 122.3(5) . . ? S1' C4 C3' 112.7(4) . . ? C3 C4 C3' 112.7(4) . . ? S1 C4 C3' 0.0(2) . . ? C10 C5 C6 118.9(5) . . ? C10 C5 C4 122.1(5) . . ? C6 C5 C4 119.1(5) . . ? C7 C6 C5 121.3(6) . . ? C6 C7 C8 119.3(6) . . ? C7 C8 C9 120.1(5) . . ? C7 C8 C11 130.8(5) . . ? C9 C8 C11 108.9(5) . . ? C10 C9 C8 119.9(5) . . ? C10 C9 C21 130.9(6) . . ? C8 C9 C21 109.1(4) . . ? C9 C10 C5 120.5(6) . . ? C12 C11 C16 120.5(5) . . ? C12 C11 C8 130.3(5) . . ? C16 C11 C8 109.0(5) . . ? C13 C12 C11 118.7(6) . . ? C12 C13 C14 122.3(6) . . ? C15 C14 C13 118.1(5) . . ? C15 C14 C17 121.4(5) . . ? C13 C14 C17 120.4(5) . . ? C16 C15 C14 120.1(6) . . ? C15 C16 C11 120.3(5) . . ? C15 C16 C21 129.2(5) . . ? C11 C16 C21 110.4(5) . . ? C14 C17 S2' 123.4(5) . . ? C14 C17 C18 123.4(5) . . ? S2' C17 C18 0.0(4) . . ? C14 C17 C18' 121.8(5) . . ? S2' C17 C18' 114.8(4) . . ? C18 C17 C18' 114.8(4) . . ? C14 C17 S2 121.8(5) . . ? S2' C17 S2 114.8(4) . . ? C18 C17 S2 114.8(4) . . ? C18' C17 S2 0.0(3) . . ? C19 C18 C17 98.0(4) . . ? C19 S2' C17 98.0(4) . . ? C20 C19 C18 117.4(6) . . ? C20 C19 S2' 117.4(6) . . ? C18 C19 S2' 0.0(4) . . ? C19 C20 S2 114.6(6) . . ? C19 C20 C18' 114.6(6) . . ? S2 C20 C18' 0.0(3) . . ? C16 C21 C9 102.4(4) . . ? C16 C21 C25 115.0(5) . . ? C9 C21 C25 113.0(5) . . ? C16 C21 C22 111.9(5) . . ? C9 C21 C22 111.8(5) . . ? C25 C21 C22 103.1(6) . . ? C23 C22 C21 103.5(6) . . ? C24 C23 C22 106.2(6) . . ? C23 C24 C25 108.5(6) . . ? C24 C25 C21 106.1(6) . . ? _refine_diff_density_max 0.466 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.069 data_p4b _database_code_CSD 158138 _journal_coden_Cambridge 1145 _publ_requested_journal 'Journal of Materials Chemistry' loop_ _publ_author_name 'Bertini, Fabio' 'Botta, Chiara' 'Destri, Silvia' 'Marchio, Luciano' 'Pasini, Mariacecilia' 'Porzio, W.' _publ_contact_author_name 'Dr W Porzio' _publ_contact_author_address ; Dr W Porzio Istituto di Chimica delle Macromolecole de CNR via E Bassini 15 Milano 20133 ITALY ; _publ_contact_author_email 'RX@ICM.MI.CNR.IT' _publ_section_title ; Synthesis and crystal structure and optical properties of fluorenic-core oligomers ; _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C29 H24' _chemical_formula_weight 372.48 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.192(8) _cell_length_b 7.217(3) _cell_length_c 13.224(6) _cell_angle_alpha 90.00 _cell_angle_beta 117.23(5) _cell_angle_gamma 90.00 _cell_volume 1034.6(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 5.9 _cell_measurement_theta_max 10.6 _exptl_crystal_description prism _exptl_crystal_colour white _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.196 _exptl_crystal_density_method ? _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1974 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1009 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1974 _reflns_number_observed 959 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 9.99(999) _refine_ls_number_reflns 1974 _refine_ls_number_parameters 286 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1650 _refine_ls_R_factor_obs 0.0618 _refine_ls_wR_factor_all 0.1664 _refine_ls_wR_factor_obs 0.1208 _refine_ls_goodness_of_fit_all 1.008 _refine_ls_goodness_of_fit_obs 1.149 _refine_ls_restrained_S_all 1.007 _refine_ls_restrained_S_obs 1.148 _refine_ls_shift/esd_max 0.105 _refine_ls_shift/esd_mean 0.023 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.4961(5) 0.3523(17) 0.2860(5) 0.057(2) Uani 1 d . . C2 C 0.5947(5) 0.3558(16) 0.4075(5) 0.052(2) Uani 1 d . . C3 C 0.7209(6) 0.3476(14) 0.4509(5) 0.053(2) Uani 1 d . . H3 H 0.7557(6) 0.3333(14) 0.4018(5) 0.025(13) Uiso 1 calc R . C4 C 0.7968(5) 0.3603(15) 0.5667(5) 0.052(2) Uani 1 d . . C5 C 0.7424(6) 0.3652(16) 0.6381(5) 0.061(2) Uani 1 d . . H5 H 0.7924(6) 0.3629(16) 0.7163(5) 0.050(16) Uiso 1 calc R . C6 C 0.6164(6) 0.3736(15) 0.5968(5) 0.058(2) Uani 1 d . . H6 H 0.5825(6) 0.3856(15) 0.6468(5) 0.063(19) Uiso 1 calc R . C7 C 0.5401(5) 0.3641(16) 0.4807(5) 0.0515(15) Uani 1 d . . C8 C 0.4075(5) 0.3632(16) 0.4134(5) 0.050(2) Uani 1 d . . C9 C 0.3125(6) 0.3749(15) 0.4430(5) 0.055(2) Uani 1 d . . H9 H 0.3299(6) 0.3825(15) 0.5191(5) 0.063(18) Uiso 1 calc R . C10 C 0.1917(6) 0.3750(15) 0.3588(5) 0.060(2) Uani 1 d . . H10 H 0.1285(6) 0.3827(15) 0.3796(5) 0.051(16) Uiso 1 calc R . C11 C 0.1615(5) 0.3641(15) 0.2441(5) 0.053(2) Uani 1 d . . C12 C 0.2593(5) 0.3535(15) 0.2166(5) 0.055(2) Uani 1 d . . H12 H 0.2423(5) 0.3459(15) 0.1406(5) 0.046(15) Uiso 1 calc R . C13 C 0.3789(5) 0.3542(16) 0.2989(5) 0.051(2) Uani 1 d . . C14 C 0.0316(5) 0.3647(15) 0.1535(5) 0.052(2) Uani 1 d . . C15 C -0.0545(7) 0.4718(12) 0.1663(7) 0.066(2) Uani 1 d . . H15 H -0.0307(7) 0.5434(12) 0.2315(7) 0.080(27) Uiso 1 calc R . C16 C -0.1764(8) 0.4742(15) 0.0830(8) 0.085(3) Uani 1 d . . H16 H -0.2339(8) 0.5471(15) 0.0926(8) 0.071(24) Uiso 1 calc R . C17 C -0.2121(6) 0.3696(18) -0.0131(6) 0.076(2) Uani 1 d . . H17 H -0.2938(6) 0.3712(18) -0.0691(6) 0.085(21) Uiso 1 calc R . C18 C -0.1272(7) 0.2623(13) -0.0267(7) 0.074(2) Uani 1 d . . H18 H -0.1516(7) 0.1908(13) -0.0920(7) 0.152(44) Uiso 1 calc R . C19 C -0.0060(7) 0.2594(12) 0.0553(6) 0.063(2) Uani 1 d . . H19 H 0.0510(7) 0.1866(12) 0.0450(6) 0.073(24) Uiso 1 calc R . C20 C 0.9336(5) 0.3567(16) 0.6131(5) 0.054(2) Uani 1 d . . C21 C 0.9907(7) 0.2593(12) 0.5604(6) 0.060(2) Uani 1 d . . H21 H 0.9433(7) 0.1916(12) 0.4949(6) 0.056(21) Uiso 1 calc R . C22 C 1.1179(7) 0.2617(13) 0.6042(7) 0.073(2) Uani 1 d . . H22 H 1.1554(7) 0.1951(13) 0.5682(7) 0.127(38) Uiso 1 calc R . C23 C 1.1884(7) 0.3613(19) 0.6998(7) 0.080(2) Uani 1 d . . H23 H 1.2737(7) 0.3634(19) 0.7284(7) 0.081(21) Uiso 1 calc R . C24 C 1.1336(8) 0.4583(13) 0.7539(8) 0.082(3) Uani 1 d . . H24 H 1.1817(8) 0.5243(13) 0.8199(8) 0.104(31) Uiso 1 calc R . C25 C 1.0063(7) 0.4574(12) 0.7095(7) 0.070(2) Uani 1 d . . H25 H 0.9692(7) 0.5257(12) 0.7452(7) 0.085(27) Uiso 1 calc R . C26 C 0.5053(11) 0.1838(17) 0.2163(10) 0.090(4) Uani 1 d . . H26A H 0.5732(11) 0.1030(17) 0.2634(10) 0.176(55) Uiso 1 calc R . H26B H 0.4294(11) 0.1127(17) 0.1839(10) 0.442(155) Uiso 1 calc R . C27 C 0.5277(24) 0.2743(47) 0.1246(15) 0.231(12) Uani 1 d . . H27A H 0.5985(24) 0.2171(47) 0.1223(15) 0.083(26) Uiso 1 calc R . H27B H 0.4566(24) 0.2547(47) 0.0514(15) 0.580(280) Uiso 1 calc R . C28 C 0.5492(31) 0.4678(48) 0.1442(25) 0.280(16) Uani 1 d . . H28A H 0.6367(31) 0.4936(48) 0.1753(25) 2.000(1320) Uiso 1 calc R . H28B H 0.5064(31) 0.5349(48) 0.0732(25) 0.197(60) Uiso 1 calc R . C29 C 0.5065(9) 0.5246(16) 0.2205(10) 0.088(4) Uani 1 d . . H29A H 0.4265(9) 0.5834(16) 0.1797(10) 0.074(24) Uiso 1 calc R . H29B H 0.5632(9) 0.6139(16) 0.2735(10) 0.510(193) Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.055(4) 0.061(5) 0.055(4) 0.003(6) 0.026(3) 0.004(6) C2 0.053(4) 0.050(4) 0.057(4) 0.009(6) 0.028(3) 0.011(6) C3 0.067(4) 0.040(4) 0.063(4) -0.015(5) 0.038(4) -0.011(5) C4 0.059(4) 0.037(4) 0.055(4) 0.005(6) 0.022(3) 0.014(6) C5 0.070(4) 0.058(4) 0.046(4) -0.003(6) 0.017(3) 0.009(6) C6 0.068(4) 0.054(5) 0.056(4) 0.001(6) 0.032(4) 0.006(6) C7 0.063(4) 0.043(4) 0.049(4) 0.002(6) 0.027(3) 0.001(6) C8 0.062(4) 0.040(4) 0.047(4) -0.001(6) 0.026(3) -0.009(6) C9 0.069(4) 0.047(5) 0.053(4) -0.003(5) 0.033(4) -0.002(5) C10 0.062(4) 0.056(5) 0.067(4) -0.014(6) 0.033(4) 0.005(6) C11 0.065(4) 0.043(4) 0.054(4) -0.006(6) 0.029(3) -0.008(6) C12 0.063(4) 0.054(4) 0.053(4) -0.006(6) 0.031(3) -0.013(6) C13 0.053(4) 0.047(4) 0.058(4) 0.002(6) 0.029(3) 0.004(6) C14 0.050(4) 0.040(4) 0.068(4) -0.005(6) 0.028(3) -0.011(6) C15 0.059(5) 0.057(5) 0.079(5) -0.014(5) 0.030(4) -0.008(4) C16 0.065(6) 0.076(7) 0.111(7) -0.011(6) 0.038(5) 0.002(5) C17 0.060(5) 0.063(6) 0.081(5) 0.000(7) 0.010(4) 0.001(7) C18 0.072(5) 0.071(6) 0.063(5) 0.003(5) 0.017(4) 0.018(5) C19 0.079(5) 0.051(5) 0.067(5) -0.006(4) 0.041(5) 0.004(5) C20 0.052(4) 0.043(4) 0.065(4) 0.005(6) 0.025(3) 0.005(6) C21 0.062(5) 0.055(5) 0.061(5) 0.005(4) 0.028(4) -0.001(4) C22 0.073(6) 0.062(6) 0.082(6) 0.006(5) 0.035(5) 0.003(5) C23 0.061(5) 0.068(6) 0.100(6) 0.020(9) 0.027(5) 0.011(7) C24 0.072(6) 0.067(6) 0.086(6) -0.016(5) 0.018(5) -0.005(5) C25 0.057(5) 0.065(6) 0.077(5) -0.017(5) 0.023(4) 0.010(4) C26 0.081(7) 0.107(10) 0.078(8) -0.034(7) 0.034(6) 0.010(7) C27 0.331(28) 0.317(35) 0.139(14) -0.089(19) 0.187(18) -0.102(28) C28 0.506(47) 0.214(23) 0.295(30) 0.111(26) 0.336(34) 0.076(32) C29 0.060(6) 0.125(11) 0.087(8) 0.051(8) 0.040(6) 0.015(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.503(8) . ? C1 C13 1.514(8) . ? C1 C29 1.554(13) . ? C1 C26 1.561(14) . ? C2 C3 1.376(8) . ? C2 C7 1.405(7) . ? C3 C4 1.383(7) . ? C4 C5 1.380(8) . ? C4 C20 1.491(8) . ? C5 C6 1.377(8) . ? C6 C7 1.386(8) . ? C7 C8 1.445(8) . ? C8 C9 1.384(8) . ? C8 C13 1.391(7) . ? C9 C10 1.382(8) . ? C10 C11 1.390(7) . ? C11 C12 1.398(7) . ? C11 C14 1.486(8) . ? C12 C13 1.364(8) . ? C14 C15 1.375(10) . ? C14 C19 1.388(10) . ? C15 C16 1.388(10) . ? C16 C17 1.368(12) . ? C17 C18 1.370(11) . ? C18 C19 1.376(10) . ? C20 C25 1.380(10) . ? C20 C21 1.381(10) . ? C21 C22 1.386(9) . ? C22 C23 1.363(12) . ? C23 C24 1.374(11) . ? C24 C25 1.386(10) . ? C26 C27 1.51(2) . ? C27 C28 1.42(2) . ? C28 C29 1.39(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 C13 102.3(4) . . ? C2 C1 C29 110.7(9) . . ? C13 C1 C29 112.2(8) . . ? C2 C1 C26 113.9(8) . . ? C13 C1 C26 113.6(9) . . ? C29 C1 C26 104.3(6) . . ? C3 C2 C7 120.4(6) . . ? C3 C2 C1 129.8(5) . . ? C7 C2 C1 109.7(5) . . ? C2 C3 C4 120.8(5) . . ? C5 C4 C3 118.2(6) . . ? C5 C4 C20 121.1(6) . . ? C3 C4 C20 120.6(5) . . ? C6 C5 C4 121.9(6) . . ? C5 C6 C7 119.9(6) . . ? C6 C7 C2 118.4(6) . . ? C6 C7 C8 132.6(5) . . ? C2 C7 C8 108.9(5) . . ? C9 C8 C13 119.0(5) . . ? C9 C8 C7 132.1(5) . . ? C13 C8 C7 108.9(5) . . ? C10 C9 C8 119.6(5) . . ? C9 C10 C11 122.1(6) . . ? C10 C11 C12 117.1(5) . . ? C10 C11 C14 122.2(5) . . ? C12 C11 C14 120.7(5) . . ? C13 C12 C11 121.3(5) . . ? C12 C13 C8 120.9(5) . . ? C12 C13 C1 129.0(5) . . ? C8 C13 C1 110.1(5) . . ? C15 C14 C19 118.6(6) . . ? C15 C14 C11 119.6(7) . . ? C19 C14 C11 121.8(8) . . ? C14 C15 C16 120.6(8) . . ? C17 C16 C15 120.1(9) . . ? C16 C17 C18 119.7(7) . . ? C19 C18 C17 120.6(8) . . ? C18 C19 C14 120.4(8) . . ? C25 C20 C21 118.4(6) . . ? C25 C20 C4 119.7(7) . . ? C21 C20 C4 121.9(7) . . ? C20 C21 C22 120.6(8) . . ? C23 C22 C21 120.3(8) . . ? C24 C23 C22 120.1(8) . . ? C23 C24 C25 119.6(9) . . ? C20 C25 C24 121.0(8) . . ? C27 C26 C1 103.1(14) . . ? C28 C27 C26 111.4(17) . . ? C29 C28 C27 108.8(21) . . ? C28 C29 C1 108.8(14) . . ? _refine_diff_density_max 0.170 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.033