# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_tahani1m #TrackingRef '16931_web_deposit_cif_file_0_SergeyPogodin_1358410565.dibenzo[ah]fluorenone_Tahani13L.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H12 O' _chemical_formula_sum 'C21 H12 O' _chemical_formula_weight 280.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 13.3493(8) _cell_length_b 7.6721(5) _cell_length_c 13.0564(8) _cell_angle_alpha 90.00 _cell_angle_beta 93.1950(10) _cell_angle_gamma 90.00 _cell_volume 1335.12(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(1) _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14046 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0187 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2909 _reflns_number_gt 2688 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0536P)^2^+0.7452P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2909 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1286 _refine_ls_wR_factor_gt 0.1258 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.72691(13) 0.7880(2) 0.57488(13) 0.0316(4) Uani 1 1 d . . . H1 H 0.6821 0.8485 0.6164 0.038 Uiso 1 1 calc R . . C2 C 0.82770(14) 0.7906(2) 0.59994(14) 0.0383(4) Uani 1 1 d . . . H2 H 0.8524 0.8536 0.6587 0.046 Uiso 1 1 calc R . . C3 C 0.89504(13) 0.7013(2) 0.54009(15) 0.0384(4) Uani 1 1 d . . . H3 H 0.9648 0.7049 0.5586 0.046 Uiso 1 1 calc R . . C4 C 0.86155(13) 0.6096(2) 0.45566(14) 0.0346(4) Uani 1 1 d . . . H4 H 0.9080 0.5492 0.4161 0.042 Uiso 1 1 calc R . . C4A C 0.75734(12) 0.6037(2) 0.42641(12) 0.0286(4) Uani 1 1 d . . . C5 C 0.72091(12) 0.5090(2) 0.33922(12) 0.0303(4) Uani 1 1 d . . . H5 H 0.7671 0.4466 0.3003 0.036 Uiso 1 1 calc R . . C6 C 0.62130(12) 0.5045(2) 0.30920(12) 0.0286(4) Uani 1 1 d . . . H6 H 0.5985 0.4415 0.2497 0.034 Uiso 1 1 calc R . . C6A C 0.55320(12) 0.59492(19) 0.36807(11) 0.0243(3) Uani 1 1 d . . . C6B C 0.44320(12) 0.61028(19) 0.35208(11) 0.0247(3) Uani 1 1 d . . . C7 C 0.37853(12) 0.5466(2) 0.27716(12) 0.0270(3) Uani 1 1 d . . . H7 H 0.4020 0.4746 0.2244 0.032 Uiso 1 1 calc R . . C7A C 0.27456(12) 0.5902(2) 0.27940(12) 0.0279(3) Uani 1 1 d . . . C8 C 0.20471(13) 0.5341(2) 0.20092(13) 0.0331(4) Uani 1 1 d . . . H8 H 0.2265 0.4624 0.1471 0.040 Uiso 1 1 calc R . . C9 C 0.10582(14) 0.5822(2) 0.20162(15) 0.0390(4) Uani 1 1 d . . . H9 H 0.0599 0.5444 0.1480 0.047 Uiso 1 1 calc R . . C10 C 0.07181(13) 0.6864(2) 0.28064(15) 0.0392(4) Uani 1 1 d . . . H10 H 0.0033 0.7201 0.2799 0.047 Uiso 1 1 calc R . . C11 C 0.13713(13) 0.7398(2) 0.35905(14) 0.0350(4) Uani 1 1 d . . . H11 H 0.1130 0.8079 0.4132 0.042 Uiso 1 1 calc R . . C11A C 0.24019(12) 0.6950(2) 0.36045(12) 0.0277(3) Uani 1 1 d . . . C12 C 0.31022(12) 0.7556(2) 0.43914(12) 0.0282(3) Uani 1 1 d . . . H12 H 0.2884 0.8232 0.4946 0.034 Uiso 1 1 calc R . . C12A C 0.40861(12) 0.71468(19) 0.43319(11) 0.0251(3) Uani 1 1 d . . . C13 C 0.49744(12) 0.7659(2) 0.50233(12) 0.0259(3) Uani 1 1 d . . . C13A C 0.58604(12) 0.68690(19) 0.45509(11) 0.0251(3) Uani 1 1 d . . . C13B C 0.68922(11) 0.69564(19) 0.48740(11) 0.0245(3) Uani 1 1 d . . . O1 O 0.49606(9) 0.85218(16) 0.58050(8) 0.0341(3) 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 0.0383(9) 0.0261(8) 0.0305(8) 0.0003(6) 0.0010(7) -0.0004(7) C2 0.0406(10) 0.0331(9) 0.0404(10) -0.0024(7) -0.0066(8) -0.0038(8) C3 0.0274(8) 0.0368(9) 0.0504(11) 0.0029(8) -0.0042(7) -0.0025(7) C4 0.0296(9) 0.0314(9) 0.0434(10) 0.0051(7) 0.0062(7) 0.0022(7) C4A 0.0319(8) 0.0235(7) 0.0308(8) 0.0047(6) 0.0054(6) -0.0004(6) C5 0.0339(9) 0.0267(8) 0.0312(8) -0.0011(6) 0.0099(7) 0.0037(7) C6 0.0341(9) 0.0262(8) 0.0258(7) -0.0003(6) 0.0051(6) 0.0007(6) C6A 0.0297(8) 0.0195(7) 0.0239(7) 0.0042(6) 0.0026(6) -0.0012(6) C6B 0.0301(8) 0.0199(7) 0.0245(7) 0.0050(6) 0.0053(6) 0.0023(6) C7 0.0333(8) 0.0230(7) 0.0249(7) 0.0018(6) 0.0039(6) 0.0008(6) C7A 0.0335(9) 0.0225(7) 0.0278(8) 0.0071(6) 0.0019(6) -0.0013(6) C8 0.0375(9) 0.0281(8) 0.0333(8) 0.0028(7) -0.0014(7) -0.0020(7) C9 0.0354(9) 0.0373(9) 0.0431(10) 0.0070(8) -0.0086(8) -0.0051(8) C10 0.0269(8) 0.0410(10) 0.0495(11) 0.0105(8) 0.0006(7) 0.0021(7) C11 0.0332(9) 0.0351(9) 0.0373(9) 0.0061(7) 0.0064(7) 0.0030(7) C11A 0.0308(8) 0.0241(7) 0.0285(8) 0.0073(6) 0.0047(6) 0.0009(6) C12 0.0336(8) 0.0251(7) 0.0264(8) 0.0034(6) 0.0066(6) 0.0036(6) C12A 0.0321(8) 0.0205(7) 0.0229(7) 0.0046(6) 0.0036(6) 0.0007(6) C13 0.0320(8) 0.0211(7) 0.0247(7) 0.0043(6) 0.0039(6) 0.0010(6) C13A 0.0328(8) 0.0199(7) 0.0230(7) 0.0038(6) 0.0047(6) 0.0007(6) C13B 0.0287(8) 0.0200(7) 0.0251(7) 0.0050(6) 0.0031(6) 0.0000(6) O1 0.0406(7) 0.0351(6) 0.0269(6) -0.0070(5) 0.0050(5) 0.0029(5) _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 1.367(2) . ? C1 C13B 1.413(2) . ? C1 H1 0.9500 . ? C2 C3 1.402(3) . ? C2 H2 0.9500 . ? C3 C4 1.362(3) . ? C3 H3 0.9500 . ? C4 C4A 1.423(2) . ? C4 H4 0.9500 . ? C4A C5 1.414(2) . ? C4A C13B 1.428(2) . ? C5 C6 1.366(2) . ? C5 H5 0.9500 . ? C6 C6A 1.406(2) . ? C6 H6 0.9500 . ? C6A C13A 1.388(2) . ? C6A C6B 1.476(2) . ? C6B C7 1.359(2) . ? C6B C12A 1.425(2) . ? C7 C7A 1.430(2) . ? C7 H7 0.9500 . ? C7A C8 1.414(2) . ? C7A C11A 1.425(2) . ? C8 C9 1.371(3) . ? C8 H8 0.9500 . ? C9 C10 1.401(3) . ? C9 H9 0.9500 . ? C10 C11 1.370(3) . ? C10 H10 0.9500 . ? C11 C11A 1.417(2) . ? C11 H11 0.9500 . ? C11A C12 1.428(2) . ? C12 C12A 1.357(2) . ? C12 H12 0.9500 . ? C12A C13 1.502(2) . ? C13 O1 1.2174(19) . ? C13 C13A 1.493(2) . ? C13A C13B 1.419(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 C13B 120.15(16) . . ? C2 C1 H1 119.9 . . ? C13B C1 H1 119.9 . . ? C1 C2 C3 120.84(17) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 120.77(17) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C4A 120.36(16) . . ? C3 C4 H4 119.8 . . ? C4A C4 H4 119.8 . . ? C5 C4A C4 121.31(15) . . ? C5 C4A C13B 120.12(15) . . ? C4 C4A C13B 118.57(15) . . ? C6 C5 C4A 121.99(15) . . ? C6 C5 H5 119.0 . . ? C4A C5 H5 119.0 . . ? C5 C6 C6A 118.66(15) . . ? C5 C6 H6 120.7 . . ? C6A C6 H6 120.7 . . ? C13A C6A C6 120.94(15) . . ? C13A C6A C6B 109.97(13) . . ? C6 C6A C6B 129.09(14) . . ? C7 C6B C12A 121.19(14) . . ? C7 C6B C6A 131.30(14) . . ? C12A C6B C6A 107.50(13) . . ? C6B C7 C7A 118.67(14) . . ? C6B C7 H7 120.7 . . ? C7A C7 H7 120.7 . . ? C8 C7A C11A 118.90(15) . . ? C8 C7A C7 121.07(15) . . ? C11A C7A C7 120.02(14) . . ? C9 C8 C7A 120.65(17) . . ? C9 C8 H8 119.7 . . ? C7A C8 H8 119.7 . . ? C8 C9 C10 120.67(17) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C11 C10 C9 120.15(17) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C11A 120.94(17) . . ? C10 C11 H11 119.5 . . ? C11A C11 H11 119.5 . . ? C11 C11A C7A 118.67(15) . . ? C11 C11A C12 121.78(15) . . ? C7A C11A C12 119.53(14) . . ? C12A C12 C11A 118.73(15) . . ? C12A C12 H12 120.6 . . ? C11A C12 H12 120.6 . . ? C12 C12A C6B 121.82(15) . . ? C12 C12A C13 129.75(14) . . ? C6B C12A C13 108.43(13) . . ? O1 C13 C13A 128.06(15) . . ? O1 C13 C12A 126.71(15) . . ? C13A C13 C12A 105.22(13) . . ? C6A C13A C13B 121.63(14) . . ? C6A C13A C13 108.87(14) . . ? C13B C13A C13 129.50(14) . . ? C1 C13B C13A 124.06(15) . . ? C1 C13B C4A 119.30(15) . . ? C13A C13B C4A 116.64(14) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.325 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 920378' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_[M06]_Sergey_S1701_P21/n #TrackingRef '16932_web_deposit_cif_file_0_SergeyPogodin_1358410772.M06_1.cif' #------------------------------------------------------------------------------ _audit_creation_date 'Sun Sep 9 09:49:20 2012' _audit_creation_method 'from TEXRAY.INF file' _audit_update_record ? #------------------------------------------------------------------------------ _computing_data_collection 'Philips 1100/20 Diffractometer Control' _computing_cell_refinement 'Philips 1100/20 Diffractometer Control' _computing_data_reduction teXsan _computing_structure_solution ? _computing_structure_refinement teXsan _computing_publication_material teXsan #------------------------------------------------------------------------------ _cell_length_a 16.7530 _cell_length_b 14.3950 _cell_length_c 5.7930 _cell_angle_alpha 90 _cell_angle_beta 91 _cell_angle_gamma 90 _cell_volume 1396.7300 _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 24 _cell_measurement_theta_min 13.5 _cell_measurement_theta_max 14.9 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' 1/2-x,1/2+y,1/2-z ' -x, -y, -z' 1/2+x,1/2-y,1/2+z #------------------------------------------------------------------------------ _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_density_diffrn 1.333 _exptl_crystal_density_meas ? _chemical_formula_weight 280.33 _chemical_formula_moiety ? _exptl_crystal_F_000 584.00 _exptl_absorpt_coefficient_mu 0.075 #------------------------------------------------------------------------------ _diffrn_special_details none _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoKalpha _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector ? _diffrn_measurement_device 'Philips 1100/20' _diffrn_measurement_method 'omega scans with profile analysis' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_decay_% 0.00 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 10 5 1 2 8 1 1 2 4 _diffrn_reflns_number 3648 _reflns_number_total 3648 _reflns_number_observed 2337 _reflns_observed_criterion 3.00 _diffrn_reflns_av_R_equivalents 3.28 _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_reduction_process ? _diffrn_orient_matrix_UB_11 0.00000 _diffrn_orient_matrix_UB_12 0.00000 _diffrn_orient_matrix_UB_13 0.00000 _diffrn_orient_matrix_UB_21 0.00000 _diffrn_orient_matrix_UB_22 0.00000 _diffrn_orient_matrix_UB_23 0.00000 _diffrn_orient_matrix_UB_31 0.00000 _diffrn_orient_matrix_UB_32 0.00000 _diffrn_orient_matrix_UB_33 0.00000 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 84 0.003 0.002 'International Tables' H 0 48 0.000 0.000 'International Tables' O 0 4 0.011 0.006 'International Tables' #------------------------------------------------------------------------------ loop_ _atom_site_label _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_calc_flag _atom_site_calc_attached_atom O(1) 0.56599(7) 0.40224(9) 0.2865(2) 0.0689 Uani ? ? C(1) 0.90636(9) 0.3142(1) 0.5057(3) 0.0436 Uani ? ? C(2) 0.96959(9) 0.2576(1) 0.4614(3) 0.0524 Uani ? ? C(3) 0.9746(1) 0.2105(1) 0.2494(3) 0.0566 Uani ? ? C(4) 0.9140(1) 0.2170(1) 0.0918(3) 0.0525 Uani ? ? C(4a) 0.84459(9) 0.2706(1) 0.1339(2) 0.0432 Uani ? ? C(5) 0.77680(10) 0.2656(1) -0.0153(3) 0.0490 Uani ? ? C(6) 0.7069(1) 0.3072(1) 0.0419(3) 0.0490 Uani ? ? C(6a) 0.70545(8) 0.36235(10) 0.2403(2) 0.0423 Uani ? ? C(7) 0.63532(9) 0.4065(1) 0.3512(3) 0.0480 Uani ? ? C(7a) 0.66792(9) 0.45514(10) 0.5591(3) 0.0458 Uani ? ? C(8) 0.6267(1) 0.5062(1) 0.7247(3) 0.0556 Uani ? ? C(9) 0.6699(1) 0.5498(1) 0.8941(3) 0.0599 Uani ? ? C(9a) 0.7543(1) 0.5508(1) 0.8937(3) 0.0521 Uani ? ? C(10) 0.7988(1) 0.6041(1) 1.0576(3) 0.0723 Uani ? ? C(11) 0.8793(2) 0.6131(2) 1.0423(4) 0.0833 Uani ? ? C(12) 0.9202(1) 0.5717(1) 0.8613(4) 0.0692 Uani ? ? C(13) 0.8807(1) 0.5175(1) 0.7035(3) 0.0520 Uani ? ? C(13a) 0.79713(9) 0.50179(10) 0.7189(2) 0.0443 Uani ? ? C(13b) 0.75065(8) 0.44623(9) 0.5641(2) 0.0400 Uani ? ? C(13c) 0.77265(8) 0.37825(9) 0.3791(2) 0.0379 Uani ? ? C(13d) 0.84249(8) 0.32509(9) 0.3414(2) 0.0377 Uani ? ? H(1) 0.9036(8) 0.344(1) 0.654(3) 0.043(4) Uani ? ? H(2) 1.010(1) 0.248(1) 0.583(3) 0.071(5) Uani ? ? H(3) 1.021(1) 0.171(1) 0.221(3) 0.060(5) Uani ? ? H(4) 0.919(1) 0.187(1) -0.043(3) 0.066(5) Uani ? ? H(5) 0.7810(9) 0.227(1) -0.157(3) 0.053(4) Uani ? ? H(6) 0.6579(10) 0.297(1) -0.049(3) 0.053(4) Uani ? ? H(8) 0.569(1) 0.507(1) 0.708(3) 0.068(5) Uani ? ? H(9) 0.644(1) 0.584(1) 1.019(3) 0.074(5) Uani ? ? H(10) 0.767(1) 0.636(2) 1.182(4) 0.094(7) Uani ? ? H(11) 0.906(1) 0.652(2) 1.159(4) 0.100(7) Uani ? ? H(12) 0.977(1) 0.581(1) 0.855(3) 0.078(6) Uani ? ? H(13) 0.9083(9) 0.489(1) 0.571(3) 0.051(4) Uani ? ? 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) 0.0370(6) 0.0851(9) 0.0843(9) -0.0021(6) -0.0066(6) 0.0099(7) C(1) 0.0422(8) 0.0478(8) 0.0406(8) 0.0030(6) 0.0000(6) -0.0034(6) C(2) 0.0432(9) 0.0577(10) 0.0563(9) 0.0071(7) -0.0023(7) -0.0022(8) C(3) 0.0480(9) 0.0549(10) 0.067(1) 0.0100(8) 0.0101(8) -0.0073(8) C(4) 0.061(1) 0.0499(9) 0.0470(9) 0.0011(7) 0.0126(8) -0.0102(7) C(4a) 0.0511(8) 0.0428(8) 0.0357(7) -0.0050(6) 0.0041(6) 0.0008(6) C(5) 0.061(1) 0.0490(8) 0.0371(8) -0.0088(7) -0.0014(7) -0.0006(7) C(6) 0.0530(9) 0.0510(9) 0.0423(8) -0.0111(7) -0.0122(7) 0.0089(7) C(6a) 0.0408(8) 0.0419(8) 0.0442(8) -0.0028(6) -0.0022(6) 0.0099(6) C(7) 0.0387(8) 0.0485(8) 0.0567(9) -0.0007(6) -0.0018(7) 0.0163(7) C(7a) 0.0412(8) 0.0428(8) 0.0535(9) 0.0053(6) 0.0052(6) 0.0104(7) C(8) 0.050(1) 0.0494(9) 0.068(1) 0.0130(7) 0.0171(8) 0.0139(8) C(9) 0.075(1) 0.0451(9) 0.060(1) 0.0172(8) 0.0230(9) 0.0035(8) C(9a) 0.070(1) 0.0374(8) 0.0489(9) 0.0074(7) 0.0082(8) 0.0014(7) C(10) 0.103(2) 0.054(1) 0.060(1) 0.003(1) 0.008(1) -0.0163(9) C(11) 0.105(2) 0.070(1) 0.074(1) -0.013(1) -0.012(1) -0.026(1) C(12) 0.071(1) 0.060(1) 0.076(1) -0.0156(10) -0.008(1) -0.0099(10) C(13) 0.0545(10) 0.0473(9) 0.0543(9) -0.0059(7) 0.0011(7) -0.0037(7) C(13a) 0.0534(9) 0.0371(7) 0.0426(8) 0.0033(6) 0.0020(6) 0.0032(6) C(13b) 0.0429(8) 0.0368(7) 0.0404(7) 0.0034(6) 0.0037(6) 0.0053(6) C(13c) 0.0388(7) 0.0385(7) 0.0366(7) -0.0025(6) 0.0016(5) 0.0047(6) C(13d) 0.0380(7) 0.0387(7) 0.0364(7) -0.0022(6) 0.0046(6) 0.0007(6) #------------------------------------------------------------------------------ _refine_special_details ? _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method Zachariasen_type_2_Gaussian_isotropic _refine_ls_extinction_coef 44.85123 _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2337 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all ? _refine_ls_R_factor_obs 0.0390 _refine_ls_wR_factor_all ? _refine_ls_wR_factor_obs 0.0530 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_obs 1.860 _refine_ls_shift/esd_max 0.0010 _refine_ls_shift/esd_mean ? _refine_diff_density_max 0.16 _refine_diff_density_min -0.20 #------------------------------------------------------------------------------ _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(7) 1.215(2) ? ? yes C(1) C(2) 1.365(2) ? ? yes C(1) C(13d) 1.426(2) ? ? yes C(2) C(3) 1.407(2) ? ? yes C(3) C(4) 1.353(2) ? ? yes C(4) C(4a) 1.422(2) ? ? yes C(4a) C(5) 1.414(2) ? ? yes C(4a) C(13d) 1.436(2) ? ? yes C(5) C(6) 1.363(2) ? ? yes C(6) C(6a) 1.397(2) ? ? yes C(6a) C(7) 1.493(2) ? ? yes C(6a) C(13c) 1.389(2) ? ? yes C(7) C(7a) 1.487(2) ? ? yes C(7a) C(8) 1.402(2) ? ? yes C(7a) C(13b) 1.392(2) ? ? yes C(8) C(9) 1.360(3) ? ? yes C(9) C(9a) 1.414(3) ? ? yes C(9a) C(10) 1.419(3) ? ? yes C(9a) C(13a) 1.438(2) ? ? yes C(10) C(11) 1.358(3) ? ? yes C(11) C(12) 1.398(3) ? ? yes C(12) C(13) 1.363(2) ? ? yes C(13) C(13a) 1.422(2) ? ? yes C(13a) C(13b) 1.421(2) ? ? yes C(13b) C(13c) 1.503(2) ? ? yes C(13c) C(13d) 1.419(2) ? ? 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(2) C(1) C(13d) 121.0(1) ? ? ? yes C(1) C(2) C(3) 120.8(2) ? ? ? yes C(2) C(3) C(4) 119.9(2) ? ? ? yes C(3) C(4) C(4a) 121.7(1) ? ? ? yes C(4) C(4a) C(5) 121.1(1) ? ? ? yes C(4) C(4a) C(13d) 118.3(1) ? ? ? yes C(5) C(4a) C(13d) 120.4(1) ? ? ? yes C(4a) C(5) C(6) 120.8(1) ? ? ? yes C(5) C(6) C(6a) 118.6(1) ? ? ? yes C(6) C(6a) C(7) 128.5(1) ? ? ? yes C(6) C(6a) C(13c) 122.8(1) ? ? ? yes C(7) C(6a) C(13c) 108.4(1) ? ? ? yes O(1) C(7) C(6a) 127.0(2) ? ? ? yes O(1) C(7) C(7a) 127.3(2) ? ? ? yes C(6a) C(7) C(7a) 105.7(1) ? ? ? yes C(7) C(7a) C(8) 128.6(1) ? ? ? yes C(7) C(7a) C(13b) 108.8(1) ? ? ? yes C(8) C(7a) C(13b) 122.6(2) ? ? ? yes C(7a) C(8) C(9) 118.2(2) ? ? ? yes C(8) C(9) C(9a) 121.4(2) ? ? ? yes C(9) C(9a) C(10) 121.0(2) ? ? ? yes C(9) C(9a) C(13a) 120.6(2) ? ? ? yes C(10) C(9a) C(13a) 118.3(2) ? ? ? yes C(9a) C(10) C(11) 121.0(2) ? ? ? yes C(10) C(11) C(12) 120.7(2) ? ? ? yes C(11) C(12) C(13) 120.5(2) ? ? ? yes C(12) C(13) C(13a) 120.9(2) ? ? ? yes C(9a) C(13a) C(13) 118.1(1) ? ? ? yes C(9a) C(13a) C(13b) 116.5(1) ? ? ? yes C(13) C(13a) C(13b) 125.2(1) ? ? ? yes C(7a) C(13b) C(13a) 119.6(1) ? ? ? yes C(7a) C(13b) C(13c) 107.7(1) ? ? ? yes C(13a) C(13b) C(13c) 132.6(1) ? ? ? yes C(6a) C(13c) C(13b) 108.2(1) ? ? ? yes C(6a) C(13c) C(13d) 118.9(1) ? ? ? yes C(13b) C(13c) C(13d) 132.6(1) ? ? ? yes C(1) C(13d) C(4a) 117.9(1) ? ? ? yes C(1) C(13d) C(13c) 124.5(1) ? ? ? yes C(4a) C(13d) C(13c) 117.3(1) ? ? ? yes #------------------------------------------------------------------------------ _database_code_depnum_ccdc_archive 'CCDC 920382'