# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_Manuscript_No. _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_title ; Facile Air-Oxidation of Large Aromatic Hydrocarbon Bay Regions to Bay Regions Quinones.Predicted Oxygen-Sensitivity of Hydrogen-Terminated Carbon Nanotubes ; _publ_author_name ; Lawrence T. Scott,* Eric Fort ; _publ_author_address ; Department of Chemistry Merkert Chemistry Center Boston College Chestnut Hill, MA 02467 Phone: (617)5528024 Fax: (617)5522705 E-mail: lawrence.scott@bc.edu ; #===END data_C46H32O2 _database_code_depnum_ccdc_archive 'CCDC 865170' #TrackingRef 'C46H32O2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_melting_point 'not measured' _chemical_formula_moiety 'C46 H32 O2' _chemical_formula_sum 'C46 H32 O2' _chemical_formula_weight 616.72 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 trigonal _symmetry_space_group_name_H-M R3c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-y, -x, z+1/2' '-x+y, y, z+1/2' 'x, x-y, z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' '-y+2/3, -x+1/3, z+5/6' '-x+y+2/3, y+1/3, z+5/6' 'x+2/3, x-y+1/3, z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-y+1/3, -x+2/3, z+7/6' '-x+y+1/3, y+2/3, z+7/6' 'x+1/3, x-y+2/3, z+7/6' _cell_length_a 36.714(4) _cell_length_b 36.714(4) _cell_length_c 15.1151(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 17645(3) _cell_formula_units_Z 18 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 9941 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 23.70 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.045 _exptl_crystal_density_method none _exptl_crystal_F_000 5832 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9913 _exptl_absorpt_correction_T_max 0.9963 _exptl_absorpt_process_details ; Sheldrick, G.M. (2008) SADABS v2008/1. Bruker AXS Inc. Madison, WI USA. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD' _diffrn_measurement_method '0.3 deg wide \w exposures' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6887 _diffrn_reflns_av_R_equivalents 0.0631 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 43 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 24.99 _reflns_number_total 6887 _reflns_number_gt 4798 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement 'SMART, SAINT' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXP-93 (Sheldrick, 1993)' _computing_publication_material 'SHELXCIF-93 (Sheldrick, 1993)' _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^)+(0.1165P)^2^+0.2787P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6887 _refine_ls_number_parameters 433 _refine_ls_number_restraints 492 _refine_ls_R_factor_all 0.0874 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.1886 _refine_ls_wR_factor_gt 0.1718 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.039 _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 O1 O 0.70493(9) 0.74202(10) -0.1140(2) 0.0893(10) Uani 1 1 d U . . O2 O 0.73111(9) 0.74992(8) 0.05466(18) 0.0719(7) Uani 1 1 d U . . C1 C 0.67357(12) 0.74141(13) -0.0854(3) 0.0587(11) Uani 1 1 d U . . C2 C 0.63448(13) 0.71384(13) -0.1279(3) 0.0634(11) Uani 1 1 d U . . H2A H 0.6309 0.6896 -0.1580 0.076 Uiso 1 1 calc R . . C3 C 0.60254(13) 0.72208(12) -0.1255(3) 0.0537(10) Uani 1 1 d U . . H3A H 0.5768 0.7031 -0.1539 0.064 Uiso 1 1 calc R . . C4 C 0.60579(13) 0.75775(12) -0.0824(2) 0.0489(9) Uani 1 1 d U . . C5 C 0.57281(11) 0.76637(12) -0.0836(2) 0.0441(8) Uani 1 1 d U . . C6 C 0.57681(12) 0.80200(12) -0.0399(2) 0.0448(9) Uani 1 1 d U . . C7 C 0.54286(13) 0.81103(13) -0.0372(3) 0.0544(10) Uani 1 1 d U . . H7A H 0.5167 0.7920 -0.0640 0.065 Uiso 1 1 calc R . . C8 C 0.54753(13) 0.84619(13) 0.0027(3) 0.0651(12) Uani 1 1 d U . . H8A H 0.5250 0.8519 0.0027 0.078 Uiso 1 1 calc R . . C9 C 0.58562(16) 0.87395(17) 0.0440(4) 0.0933(18) Uani 1 1 d U . . H9A H 0.5888 0.8991 0.0691 0.112 Uiso 1 1 calc R . . C10 C 0.61977(12) 0.86606(12) 0.0497(2) 0.0487(9) Uani 1 1 d U . . C11 C 0.61432(12) 0.82937(12) 0.0059(2) 0.0440(8) Uani 1 1 d U . . C12 C 0.64790(11) 0.82055(11) 0.0083(2) 0.0409(8) Uani 1 1 d U . . C13 C 0.64343(11) 0.78465(11) -0.0360(2) 0.0411(9) Uani 1 1 d U . . C14 C 0.67639(12) 0.77455(12) -0.0351(3) 0.0493(9) Uani 1 1 d U . . C15 C 0.71385(12) 0.80120(12) 0.0184(2) 0.0469(9) Uani 1 1 d U . . C16 C 0.71833(12) 0.83769(11) 0.0571(2) 0.0427(8) Uani 1 1 d U . . C17 C 0.68547(11) 0.84746(11) 0.0537(2) 0.0398(8) Uani 1 1 d U . . C18 C 0.69021(12) 0.88470(12) 0.0966(2) 0.0437(9) Uani 1 1 d U . . C19 C 0.65688(12) 0.89229(11) 0.0937(2) 0.0435(8) Uani 1 1 d U . . C20 C 0.66331(15) 0.92953(13) 0.1449(3) 0.0660(12) Uani 1 1 d U . . H20A H 0.6405 0.9347 0.1519 0.079 Uiso 1 1 calc R . . C21 C 0.70159(14) 0.95677(14) 0.1824(3) 0.0634(11) Uani 1 1 d U . . H21A H 0.7057 0.9822 0.2082 0.076 Uiso 1 1 calc R . . C22 C 0.73340(13) 0.94837(12) 0.1835(3) 0.0557(10) Uani 1 1 d U . . H22A H 0.7590 0.9672 0.2126 0.067 Uiso 1 1 calc R . . C23 C 0.72929(12) 0.91203(11) 0.1420(2) 0.0427(8) Uani 1 1 d U . . C24 C 0.76249(11) 0.90262(11) 0.1427(2) 0.0432(8) Uani 1 1 d U . . C25 C 0.75744(12) 0.86642(11) 0.1007(2) 0.0447(8) Uani 1 1 d U . . C26 C 0.78985(12) 0.85661(12) 0.1007(2) 0.0484(9) Uani 1 1 d U . . H26A H 0.8163 0.8761 0.1256 0.058 Uiso 1 1 calc R . . C27 C 0.78443(13) 0.82076(13) 0.0669(3) 0.0570(10) Uani 1 1 d U . . H27A H 0.8077 0.8164 0.0618 0.068 Uiso 1 1 calc R . . C28 C 0.74438(14) 0.78933(13) 0.0388(3) 0.0693(12) Uani 1 1 d U . . C29 C 0.53194(12) 0.73728(11) -0.1285(2) 0.0471(9) Uani 1 1 d U . . C30 C 0.49850(13) 0.70427(13) -0.0843(2) 0.0515(9) Uani 1 1 d U . . C31 C 0.46087(13) 0.68085(12) -0.1270(3) 0.0579(10) Uani 1 1 d U . . H31A H 0.4381 0.6589 -0.0954 0.070 Uiso 1 1 calc R . . C32 C 0.45474(13) 0.68784(13) -0.2139(3) 0.0605(11) Uani 1 1 d U . . C33 C 0.48871(15) 0.72003(14) -0.2571(3) 0.0655(11) Uani 1 1 d U . . H33A H 0.4855 0.7252 -0.3174 0.079 Uiso 1 1 calc R . . C34 C 0.52616(12) 0.74448(13) -0.2180(2) 0.0507(9) Uani 1 1 d U . . C35 C 0.50312(16) 0.69526(16) 0.0101(3) 0.0739(13) Uani 1 1 d U . . H35A H 0.4767 0.6713 0.0309 0.111 Uiso 1 1 calc R . . H35B H 0.5100 0.7200 0.0463 0.111 Uiso 1 1 calc R . . H35C H 0.5257 0.6885 0.0151 0.111 Uiso 1 1 calc R . . C36 C 0.41176(18) 0.66181(17) -0.2567(4) 0.1010(18) Uani 1 1 d U . . H36A H 0.4130 0.6708 -0.3182 0.152 Uiso 1 1 calc R . . H36B H 0.3910 0.6658 -0.2242 0.152 Uiso 1 1 calc R . . H36C H 0.4037 0.6320 -0.2554 0.152 Uiso 1 1 calc R . . C37 C 0.56334(15) 0.77949(16) -0.2681(3) 0.0774(13) Uani 1 1 d U . . H37A H 0.5548 0.7810 -0.3287 0.116 Uiso 1 1 calc R . . H37B H 0.5866 0.7735 -0.2694 0.116 Uiso 1 1 calc R . . H37C H 0.5726 0.8064 -0.2382 0.116 Uiso 1 1 calc R . . C38 C 0.80267(11) 0.93037(11) 0.1915(2) 0.0446(9) Uani 1 1 d U . . C39 C 0.83552(14) 0.96331(13) 0.1450(3) 0.0553(10) Uani 1 1 d U . . C40 C 0.87369(14) 0.98756(13) 0.1886(3) 0.0584(11) Uani 1 1 d U . . H40A H 0.8958 1.0107 0.1581 0.070 Uiso 1 1 calc R . . C41 C 0.88055(15) 0.97952(13) 0.2727(3) 0.0652(12) Uani 1 1 d U . . C42 C 0.84719(14) 0.94767(13) 0.3181(3) 0.0598(10) Uani 1 1 d U . . H42A H 0.8513 0.9424 0.3778 0.072 Uiso 1 1 calc R . . C43 C 0.80656(13) 0.92223(13) 0.2788(3) 0.0571(10) Uani 1 1 d U . . C44 C 0.83105(16) 0.97318(16) 0.0510(3) 0.0895(17) Uani 1 1 d U . . H44A H 0.8574 0.9975 0.0312 0.134 Uiso 1 1 calc R . . H44B H 0.8082 0.9796 0.0466 0.134 Uiso 1 1 calc R . . H44C H 0.8246 0.9489 0.0136 0.134 Uiso 1 1 calc R . . C45 C 0.92186(16) 1.00587(16) 0.3168(4) 0.0966(18) Uani 1 1 d U . . H45A H 0.9417 1.0266 0.2748 0.145 Uiso 1 1 calc R . . H45B H 0.9329 0.9879 0.3373 0.145 Uiso 1 1 calc R . . H45C H 0.9183 1.0204 0.3676 0.145 Uiso 1 1 calc R . . C46 C 0.77309(15) 0.88821(15) 0.3311(3) 0.0778(13) Uani 1 1 d U . . H46A H 0.7474 0.8738 0.2955 0.117 Uiso 1 1 calc R . . H46B H 0.7676 0.9000 0.3842 0.117 Uiso 1 1 calc R . . H46C H 0.7819 0.8681 0.3485 0.117 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 O1 0.095(2) 0.126(2) 0.094(2) -0.0443(18) -0.0228(17) 0.091(2) O2 0.0894(19) 0.0770(17) 0.0775(16) -0.0094(14) -0.0128(14) 0.0628(16) C1 0.054(2) 0.076(3) 0.067(3) -0.025(2) -0.008(2) 0.049(2) C2 0.062(2) 0.055(2) 0.080(3) -0.029(2) -0.013(2) 0.035(2) C3 0.058(2) 0.056(2) 0.052(2) -0.0131(19) -0.0102(18) 0.032(2) C4 0.054(2) 0.047(2) 0.058(2) -0.0052(18) -0.0040(19) 0.0346(19) C5 0.052(2) 0.047(2) 0.0433(19) 0.0001(16) -0.0024(17) 0.0321(18) C6 0.055(2) 0.060(2) 0.0360(18) 0.0065(16) -0.0024(16) 0.0412(19) C7 0.053(2) 0.061(3) 0.065(3) -0.005(2) -0.003(2) 0.040(2) C8 0.058(3) 0.063(3) 0.097(3) -0.011(2) -0.018(2) 0.047(2) C9 0.081(3) 0.080(3) 0.149(5) -0.046(3) -0.041(3) 0.063(3) C10 0.064(2) 0.041(2) 0.055(2) 0.0005(17) -0.0046(19) 0.0363(19) C11 0.050(2) 0.052(2) 0.043(2) 0.0041(17) 0.0057(17) 0.0346(19) C12 0.0464(19) 0.045(2) 0.0408(17) -0.0024(16) -0.0032(16) 0.0303(17) C13 0.044(2) 0.042(2) 0.048(2) 0.0015(16) 0.0009(17) 0.0295(17) C14 0.052(2) 0.056(2) 0.052(2) -0.0048(19) -0.0017(18) 0.036(2) C15 0.050(2) 0.053(2) 0.050(2) -0.0016(17) -0.0009(17) 0.0348(19) C16 0.054(2) 0.0381(19) 0.048(2) 0.0032(16) -0.0023(17) 0.0318(18) C17 0.050(2) 0.0392(19) 0.0423(18) 0.0091(15) 0.0094(17) 0.0315(16) C18 0.061(2) 0.049(2) 0.0338(19) -0.0025(15) 0.0026(17) 0.0372(19) C19 0.052(2) 0.045(2) 0.045(2) 0.0059(17) 0.0063(17) 0.0329(19) C20 0.076(3) 0.061(3) 0.085(3) -0.021(2) -0.009(2) 0.053(2) C21 0.076(3) 0.069(3) 0.065(3) -0.019(2) 0.001(2) 0.051(2) C22 0.065(2) 0.046(2) 0.068(3) -0.0159(19) -0.009(2) 0.036(2) C23 0.052(2) 0.044(2) 0.0367(19) 0.0043(16) 0.0036(16) 0.0272(17) C24 0.053(2) 0.041(2) 0.0407(19) 0.0034(16) 0.0043(17) 0.0282(17) C25 0.046(2) 0.0339(18) 0.057(2) 0.0054(17) 0.0037(17) 0.0215(16) C26 0.054(2) 0.049(2) 0.053(2) 0.0012(18) -0.0043(18) 0.0339(19) C27 0.056(2) 0.064(3) 0.070(3) -0.003(2) -0.001(2) 0.044(2) C28 0.079(3) 0.052(2) 0.108(3) -0.030(2) -0.039(2) 0.056(2) C29 0.056(2) 0.047(2) 0.051(2) 0.0015(17) -0.0023(18) 0.0362(19) C30 0.053(2) 0.055(2) 0.050(2) -0.0009(19) -0.0006(18) 0.029(2) C31 0.064(3) 0.040(2) 0.067(3) 0.0039(19) 0.006(2) 0.024(2) C32 0.059(3) 0.055(3) 0.071(3) -0.004(2) -0.019(2) 0.031(2) C33 0.086(3) 0.063(3) 0.046(2) 0.003(2) -0.015(2) 0.036(2) C34 0.060(2) 0.058(2) 0.046(2) -0.0027(18) 0.0000(19) 0.039(2) C35 0.076(3) 0.080(3) 0.059(3) 0.003(2) 0.006(2) 0.034(3) C36 0.093(4) 0.081(4) 0.113(4) -0.022(3) -0.048(3) 0.031(3) C37 0.080(3) 0.092(3) 0.042(2) 0.015(2) -0.004(2) 0.029(2) C38 0.050(2) 0.050(2) 0.041(2) -0.0076(16) -0.0018(16) 0.0299(18) C39 0.067(3) 0.051(2) 0.055(2) -0.0002(19) 0.002(2) 0.035(2) C40 0.059(3) 0.055(2) 0.055(2) -0.004(2) -0.003(2) 0.024(2) C41 0.071(3) 0.050(2) 0.063(3) -0.017(2) -0.005(2) 0.022(2) C42 0.069(3) 0.064(3) 0.055(2) -0.012(2) -0.013(2) 0.040(2) C43 0.070(3) 0.052(2) 0.053(2) 0.0011(19) -0.007(2) 0.033(2) C44 0.080(3) 0.085(4) 0.069(3) 0.035(3) -0.007(3) 0.014(3) C45 0.079(3) 0.074(3) 0.097(4) 0.001(3) -0.021(3) 0.009(3) C46 0.082(3) 0.082(3) 0.073(3) 0.014(3) 0.008(3) 0.044(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 O1 C1 1.219(4) . ? O2 C28 1.298(5) . ? C1 C14 1.394(5) . ? C1 C2 1.430(6) . ? C2 C3 1.350(5) . ? C2 H2A 0.9500 . ? C3 C4 1.413(5) . ? C3 H3A 0.9500 . ? C4 C5 1.397(5) . ? C4 C13 1.418(5) . ? C5 C6 1.406(5) . ? C5 C29 1.500(5) . ? C6 C11 1.415(5) . ? C6 C7 1.441(5) . ? C7 C8 1.356(5) . ? C7 H7A 0.9500 . ? C8 C9 1.399(6) . ? C8 H8A 0.9500 . ? C9 C10 1.424(6) . ? C9 H9A 0.9500 . ? C10 C19 1.383(5) . ? C10 C11 1.423(5) . ? C11 C12 1.423(5) . ? C12 C17 1.409(3) . ? C12 C13 1.413(5) . ? C13 C14 1.432(5) . ? C14 C15 1.469(5) . ? C15 C16 1.394(5) . ? C15 C28 1.425(5) . ? C16 C17 1.421(5) . ? C16 C25 1.447(5) . ? C17 C18 1.443(5) . ? C18 C19 1.385(5) . ? C18 C23 1.449(5) . ? C19 C20 1.484(5) . ? C20 C21 1.375(6) . ? C20 H20A 0.9500 . ? C21 C22 1.349(5) . ? C21 H21A 0.9500 . ? C22 C23 1.412(5) . ? C22 H22A 0.9500 . ? C23 C24 1.424(5) . ? C24 C25 1.399(5) . ? C24 C38 1.502(5) . ? C25 C26 1.405(5) . ? C26 C27 1.331(5) . ? C26 H26A 0.9500 . ? C27 C28 1.406(6) . ? C27 H27A 0.9500 . ? C29 C30 1.390(6) . ? C29 C34 1.415(5) . ? C30 C31 1.370(6) . ? C30 C35 1.494(6) . ? C31 C32 1.378(6) . ? C31 H31A 0.9500 . ? C32 C33 1.380(6) . ? C32 C36 1.521(6) . ? C33 C34 1.346(5) . ? C33 H33A 0.9500 . ? C34 C37 1.528(6) . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 C43 1.375(5) . ? C38 C39 1.398(5) . ? C39 C40 1.394(6) . ? C39 C44 1.495(6) . ? C40 C41 1.358(6) . ? C40 H40A 0.9500 . ? C41 C42 1.381(6) . ? C41 C45 1.488(6) . ? C42 C43 1.434(6) . ? C42 H42A 0.9500 . ? C43 C46 1.470(6) . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? 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 O1 C1 C14 121.3(4) . . ? O1 C1 C2 117.3(4) . . ? C14 C1 C2 118.2(3) . . ? C3 C2 C1 120.4(4) . . ? C3 C2 H2A 119.8 . . ? C1 C2 H2A 119.8 . . ? C2 C3 C4 122.7(4) . . ? C2 C3 H3A 118.7 . . ? C4 C3 H3A 118.7 . . ? C5 C4 C3 121.5(4) . . ? C5 C4 C13 120.1(3) . . ? C3 C4 C13 118.4(3) . . ? C4 C5 C6 120.4(4) . . ? C4 C5 C29 121.1(3) . . ? C6 C5 C29 118.5(3) . . ? C5 C6 C11 120.2(3) . . ? C5 C6 C7 121.8(3) . . ? C11 C6 C7 118.0(3) . . ? C8 C7 C6 121.3(4) . . ? C8 C7 H7A 119.4 . . ? C6 C7 H7A 119.4 . . ? C7 C8 C9 119.8(4) . . ? C7 C8 H8A 120.1 . . ? C9 C8 H8A 120.1 . . ? C8 C9 C10 122.7(4) . . ? C8 C9 H9A 118.7 . . ? C10 C9 H9A 118.7 . . ? C19 C10 C11 120.4(3) . . ? C19 C10 C9 123.3(4) . . ? C11 C10 C9 116.3(4) . . ? C6 C11 C10 121.8(3) . . ? C6 C11 C12 119.8(3) . . ? C10 C11 C12 118.4(3) . . ? C17 C12 C13 120.1(2) . . ? C17 C12 C11 120.6(3) . . ? C13 C12 C11 119.4(3) . . ? C12 C13 C4 120.1(3) . . ? C12 C13 C14 121.2(3) . . ? C4 C13 C14 118.6(3) . . ? C1 C14 C13 121.2(3) . . ? C1 C14 C15 121.2(3) . . ? C13 C14 C15 117.6(3) . . ? C16 C15 C28 118.0(3) . . ? C16 C15 C14 119.5(3) . . ? C28 C15 C14 122.2(3) . . ? C15 C16 C17 121.3(3) . . ? C15 C16 C25 119.3(3) . . ? C17 C16 C25 119.4(3) . . ? C12 C17 C16 119.8(3) . . ? C12 C17 C18 119.7(2) . . ? C16 C17 C18 120.5(3) . . ? C19 C18 C17 118.5(3) . . ? C19 C18 C23 123.0(3) . . ? C17 C18 C23 118.6(3) . . ? C10 C19 C18 122.5(3) . . ? C10 C19 C20 122.7(3) . . ? C18 C19 C20 114.8(4) . . ? C21 C20 C19 121.3(4) . . ? C21 C20 H20A 119.4 . . ? C19 C20 H20A 119.4 . . ? C22 C21 C20 121.7(4) . . ? C22 C21 H21A 119.1 . . ? C20 C21 H21A 119.1 . . ? C21 C22 C23 121.0(4) . . ? C21 C22 H22A 119.5 . . ? C23 C22 H22A 119.5 . . ? C22 C23 C24 121.8(3) . . ? C22 C23 C18 117.8(3) . . ? C24 C23 C18 120.4(3) . . ? C25 C24 C23 120.3(3) . . ? C25 C24 C38 119.1(3) . . ? C23 C24 C38 120.5(3) . . ? C24 C25 C26 121.1(3) . . ? C24 C25 C16 120.7(3) . . ? C26 C25 C16 118.2(3) . . ? C27 C26 C25 121.7(4) . . ? C27 C26 H26A 119.1 . . ? C25 C26 H26A 119.1 . . ? C26 C27 C28 120.4(4) . . ? C26 C27 H27A 119.8 . . ? C28 C27 H27A 119.8 . . ? O2 C28 C27 121.0(3) . . ? O2 C28 C15 117.8(4) . . ? C27 C28 C15 118.3(3) . . ? C30 C29 C34 118.2(4) . . ? C30 C29 C5 122.5(3) . . ? C34 C29 C5 119.3(3) . . ? C31 C30 C29 119.7(4) . . ? C31 C30 C35 120.1(4) . . ? C29 C30 C35 120.2(4) . . ? C30 C31 C32 122.6(4) . . ? C30 C31 H31A 118.7 . . ? C32 C31 H31A 118.7 . . ? C31 C32 C33 116.6(4) . . ? C31 C32 C36 120.2(4) . . ? C33 C32 C36 123.1(4) . . ? C34 C33 C32 123.2(4) . . ? C34 C33 H33A 118.4 . . ? C32 C33 H33A 118.4 . . ? C33 C34 C29 119.6(4) . . ? C33 C34 C37 121.9(3) . . ? C29 C34 C37 118.5(3) . . ? C30 C35 H35A 109.5 . . ? C30 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C30 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C32 C36 H36A 109.5 . . ? C32 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C32 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C34 C37 H37A 109.5 . . ? C34 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C34 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C43 C38 C39 122.2(4) . . ? C43 C38 C24 119.8(3) . . ? C39 C38 C24 118.0(3) . . ? C40 C39 C38 118.1(4) . . ? C40 C39 C44 119.4(4) . . ? C38 C39 C44 122.4(4) . . ? C41 C40 C39 122.7(4) . . ? C41 C40 H40A 118.6 . . ? C39 C40 H40A 118.6 . . ? C40 C41 C42 117.9(4) . . ? C40 C41 C45 121.2(4) . . ? C42 C41 C45 120.8(4) . . ? C41 C42 C43 122.6(4) . . ? C41 C42 H42A 118.7 . . ? C43 C42 H42A 118.7 . . ? C38 C43 C42 116.3(4) . . ? C38 C43 C46 124.5(4) . . ? C42 C43 C46 119.1(4) . . ? C39 C44 H44A 109.5 . . ? C39 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C39 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C41 C45 H45A 109.5 . . ? C41 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C41 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C43 C46 H46A 109.5 . . ? C43 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C43 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? 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 O1 C1 C2 C3 -154.4(4) . . . . ? C14 C1 C2 C3 5.7(7) . . . . ? C1 C2 C3 C4 0.4(7) . . . . ? C2 C3 C4 C5 177.6(4) . . . . ? C2 C3 C4 C13 -3.4(6) . . . . ? C3 C4 C5 C6 179.8(4) . . . . ? C13 C4 C5 C6 0.8(5) . . . . ? C3 C4 C5 C29 2.0(6) . . . . ? C13 C4 C5 C29 -177.0(3) . . . . ? C4 C5 C6 C11 -0.2(5) . . . . ? C29 C5 C6 C11 177.7(3) . . . . ? C4 C5 C6 C7 -177.8(4) . . . . ? C29 C5 C6 C7 0.1(5) . . . . ? C5 C6 C7 C8 -177.9(4) . . . . ? C11 C6 C7 C8 4.4(6) . . . . ? C6 C7 C8 C9 -1.4(7) . . . . ? C7 C8 C9 C10 -3.0(8) . . . . ? C8 C9 C10 C19 -177.0(5) . . . . ? C8 C9 C10 C11 4.0(8) . . . . ? C5 C6 C11 C10 179.0(3) . . . . ? C7 C6 C11 C10 -3.3(6) . . . . ? C5 C6 C11 C12 -0.5(5) . . . . ? C7 C6 C11 C12 177.2(3) . . . . ? C19 C10 C11 C6 -179.8(3) . . . . ? C9 C10 C11 C6 -0.8(6) . . . . ? C19 C10 C11 C12 -0.2(5) . . . . ? C9 C10 C11 C12 178.8(4) . . . . ? C6 C11 C12 C17 -180.0(3) . . . . ? C10 C11 C12 C17 0.5(4) . . . . ? C6 C11 C12 C13 0.6(5) . . . . ? C10 C11 C12 C13 -179.0(3) . . . . ? C17 C12 C13 C4 -179.4(3) . . . . ? C11 C12 C13 C4 0.0(5) . . . . ? C17 C12 C13 C14 0.7(5) . . . . ? C11 C12 C13 C14 -179.9(3) . . . . ? C5 C4 C13 C12 -0.7(5) . . . . ? C3 C4 C13 C12 -179.8(3) . . . . ? C5 C4 C13 C14 179.2(3) . . . . ? C3 C4 C13 C14 0.2(5) . . . . ? O1 C1 C14 C13 150.4(4) . . . . ? C2 C1 C14 C13 -9.0(6) . . . . ? O1 C1 C14 C15 -27.6(6) . . . . ? C2 C1 C14 C15 173.0(4) . . . . ? C12 C13 C14 C1 -174.0(4) . . . . ? C4 C13 C14 C1 6.1(6) . . . . ? C12 C13 C14 C15 4.1(5) . . . . ? C4 C13 C14 C15 -175.8(3) . . . . ? C1 C14 C15 C16 170.4(4) . . . . ? C13 C14 C15 C16 -7.7(5) . . . . ? C1 C14 C15 C28 -15.1(6) . . . . ? C13 C14 C15 C28 166.8(4) . . . . ? C28 C15 C16 C17 -168.1(4) . . . . ? C14 C15 C16 C17 6.6(5) . . . . ? C28 C15 C16 C25 12.7(5) . . . . ? C14 C15 C16 C25 -172.6(3) . . . . ? C13 C12 C17 C16 -2.0(4) . . . . ? C11 C12 C17 C16 178.6(4) . . . . ? C13 C12 C17 C18 178.2(4) . . . . ? C11 C12 C17 C18 -1.2(4) . . . . ? C15 C16 C17 C12 -1.8(4) . . . . ? C25 C16 C17 C12 177.4(3) . . . . ? C15 C16 C17 C18 178.0(3) . . . . ? C25 C16 C17 C18 -2.8(5) . . . . ? C12 C17 C18 C19 1.7(4) . . . . ? C16 C17 C18 C19 -178.1(3) . . . . ? C12 C17 C18 C23 -179.4(3) . . . . ? C16 C17 C18 C23 0.8(5) . . . . ? C11 C10 C19 C18 0.8(6) . . . . ? C9 C10 C19 C18 -178.2(4) . . . . ? C11 C10 C19 C20 -176.3(3) . . . . ? C9 C10 C19 C20 4.8(6) . . . . ? C17 C18 C19 C10 -1.5(5) . . . . ? C23 C18 C19 C10 179.7(3) . . . . ? C17 C18 C19 C20 175.8(3) . . . . ? C23 C18 C19 C20 -3.0(5) . . . . ? C10 C19 C20 C21 -175.1(4) . . . . ? C18 C19 C20 C21 7.6(6) . . . . ? C19 C20 C21 C22 -8.0(7) . . . . ? C20 C21 C22 C23 3.2(7) . . . . ? C21 C22 C23 C24 -179.9(4) . . . . ? C21 C22 C23 C18 1.5(6) . . . . ? C19 C18 C23 C22 -1.3(5) . . . . ? C17 C18 C23 C22 179.9(3) . . . . ? C19 C18 C23 C24 -180.0(3) . . . . ? C17 C18 C23 C24 1.2(5) . . . . ? C22 C23 C24 C25 -179.8(3) . . . . ? C18 C23 C24 C25 -1.2(5) . . . . ? C22 C23 C24 C38 2.8(5) . . . . ? C18 C23 C24 C38 -178.6(3) . . . . ? C23 C24 C25 C26 -179.9(3) . . . . ? C38 C24 C25 C26 -2.5(5) . . . . ? C23 C24 C25 C16 -0.9(5) . . . . ? C38 C24 C25 C16 176.6(3) . . . . ? C15 C16 C25 C24 -177.9(3) . . . . ? C17 C16 C25 C24 2.9(5) . . . . ? C15 C16 C25 C26 1.1(5) . . . . ? C17 C16 C25 C26 -178.1(3) . . . . ? C24 C25 C26 C27 174.9(4) . . . . ? C16 C25 C26 C27 -4.2(6) . . . . ? C25 C26 C27 C28 -7.1(6) . . . . ? C26 C27 C28 O2 -139.0(4) . . . . ? C26 C27 C28 C15 21.3(7) . . . . ? C16 C15 C28 O2 137.2(4) . . . . ? C14 C15 C28 O2 -37.4(6) . . . . ? C16 C15 C28 C27 -23.8(6) . . . . ? C14 C15 C28 C27 161.6(4) . . . . ? C4 C5 C29 C30 90.5(5) . . . . ? C6 C5 C29 C30 -87.3(4) . . . . ? C4 C5 C29 C34 -92.3(4) . . . . ? C6 C5 C29 C34 89.8(4) . . . . ? C34 C29 C30 C31 -2.3(5) . . . . ? C5 C29 C30 C31 174.9(3) . . . . ? C34 C29 C30 C35 179.7(4) . . . . ? C5 C29 C30 C35 -3.1(6) . . . . ? C29 C30 C31 C32 1.7(6) . . . . ? C35 C30 C31 C32 179.7(4) . . . . ? C30 C31 C32 C33 0.0(6) . . . . ? C30 C31 C32 C36 -177.8(4) . . . . ? C31 C32 C33 C34 -1.2(6) . . . . ? C36 C32 C33 C34 176.6(4) . . . . ? C32 C33 C34 C29 0.6(6) . . . . ? C32 C33 C34 C37 179.1(4) . . . . ? C30 C29 C34 C33 1.2(5) . . . . ? C5 C29 C34 C33 -176.1(4) . . . . ? C30 C29 C34 C37 -177.4(3) . . . . ? C5 C29 C34 C37 5.3(5) . . . . ? C25 C24 C38 C43 -87.4(4) . . . . ? C23 C24 C38 C43 90.0(4) . . . . ? C25 C24 C38 C39 90.9(4) . . . . ? C23 C24 C38 C39 -91.6(4) . . . . ? C43 C38 C39 C40 2.1(6) . . . . ? C24 C38 C39 C40 -176.2(3) . . . . ? C43 C38 C39 C44 -178.0(4) . . . . ? C24 C38 C39 C44 3.7(6) . . . . ? C38 C39 C40 C41 2.4(6) . . . . ? C44 C39 C40 C41 -177.6(5) . . . . ? C39 C40 C41 C42 -4.4(6) . . . . ? C39 C40 C41 C45 179.4(4) . . . . ? C40 C41 C42 C43 2.2(6) . . . . ? C45 C41 C42 C43 178.4(4) . . . . ? C39 C38 C43 C42 -4.0(6) . . . . ? C24 C38 C43 C42 174.2(3) . . . . ? C39 C38 C43 C46 179.7(4) . . . . ? C24 C38 C43 C46 -2.0(6) . . . . ? C41 C42 C43 C38 1.9(6) . . . . ? C41 C42 C43 C46 178.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.358 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.049 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 -0.040 96 12 ' ' 2 0.000 0.000 0.222 19 3 ' ' 3 0.000 0.000 0.460 96 12 ' ' 4 0.000 0.000 0.721 18 3 ' ' 5 0.000 0.333 0.457 613 135 ' ' 6 0.000 0.667 0.441 614 135 ' ' 7 0.333 0.333 0.782 614 135 ' ' 8 0.333 1.000 0.280 614 135 ' ' 9 0.333 0.667 0.127 96 12 ' ' 10 0.333 0.667 0.627 96 12 ' ' 11 0.333 0.667 0.887 18 3 ' ' 12 0.333 0.667 0.387 18 3 ' ' 13 0.667 0.000 0.449 613 135 ' ' 14 0.667 0.667 0.947 614 135 ' ' 15 0.667 0.333 0.793 97 12 ' ' 16 0.667 0.333 0.293 97 12 ' ' 17 0.667 0.333 0.554 18 3 ' ' 18 0.667 0.333 0.054 18 3 ' ' _platon_squeeze_details ; ;