# 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_111117b_lyx_03_55CIS #TrackingRef '9230_web_deposit_cif_file_0_YexinLi_1327470674.CTNAB.cif' _audit_creation_date 2011-05-25 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C34 H24' _chemical_formula_sum 'C34 H24' _chemical_formula_weight 432.53 _chemical_melting_point ? _chemical_oxdiff_formula 'C H' 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 16.850(4) _cell_length_b 6.4351(18) _cell_length_c 22.782(6) _cell_angle_alpha 90.00 _cell_angle_beta 107.41(3) _cell_angle_gamma 90.00 _cell_volume 2357.1(11) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1092 _cell_measurement_temperature 291.15 _cell_measurement_theta_max 28.7721 _cell_measurement_theta_min 3.1657 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.90639 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 912 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0706 _diffrn_reflns_av_unetI/netI 0.1232 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 12323 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.30 _diffrn_ambient_temperature 291.15 _diffrn_detector_area_resol_mean 16.0355 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -42.00 17.00 1.0000 71.6100 omega____ theta____ kappa____ phi______ frames - 17.1176 -77.0000 -180.0000 59 #__ type_ start__ end____ width___ exp.time_ 2 omega 20.00 45.00 1.0000 71.6100 omega____ theta____ kappa____ phi______ frames - 17.1176 -77.0000 -60.0000 25 #__ type_ start__ end____ width___ exp.time_ 3 omega -11.00 86.00 1.0000 71.6100 omega____ theta____ kappa____ phi______ frames - 17.1176 77.0000 60.0000 97 #__ type_ start__ end____ width___ exp.time_ 4 omega -69.00 -27.00 1.0000 71.6100 omega____ theta____ kappa____ phi______ frames - -19.2269 116.0000 133.0000 42 #__ type_ start__ end____ width___ exp.time_ 5 omega -13.00 62.00 1.0000 71.6100 omega____ theta____ kappa____ phi______ frames - 17.1176 77.0000 -120.0000 75 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0048828000 _diffrn_orient_matrix_UB_12 -0.0007445000 _diffrn_orient_matrix_UB_13 -0.0298864000 _diffrn_orient_matrix_UB_21 -0.0067262000 _diffrn_orient_matrix_UB_22 0.1086256000 _diffrn_orient_matrix_UB_23 -0.0021310000 _diffrn_orient_matrix_UB_31 0.0433960000 _diffrn_orient_matrix_UB_32 0.0170003000 _diffrn_orient_matrix_UB_33 0.0130335000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1861 _reflns_number_total 4787 _reflns_odcompleteness_completeness 99.62 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.248 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.037 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 307 _refine_ls_number_reflns 4787 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2100 _refine_ls_R_factor_gt 0.0718 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0419P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1227 _refine_ls_wR_factor_ref 0.1774 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 C9 C 0.11333(18) 0.4331(5) 0.33156(13) 0.0461(9) Uani 1 1 d . . . C14 C 0.09152(19) 0.3085(5) 0.37522(14) 0.0484(9) Uani 1 1 d . . . C1 C 0.0223(2) 0.3623(6) 0.39448(14) 0.0512(9) Uani 1 1 d . . . C7 C 0.0029(2) 0.6743(6) 0.33263(15) 0.0593(10) Uani 1 1 d . . . H7 H -0.0252 0.7982 0.3196 0.071 Uiso 1 1 calc R . . C8 C 0.0681(2) 0.6203(6) 0.31035(15) 0.0521(9) Uani 1 1 d . . . C16 C 0.18090(18) 0.0853(5) 0.45835(14) 0.0525(9) Uani 1 1 d . . . H16 H 0.1709 0.1785 0.4865 0.063 Uiso 1 1 calc R . . C20 C 0.35122(19) -0.4035(5) 0.53612(15) 0.0507(9) Uani 1 1 d . . . C17 C 0.23682(18) -0.0866(5) 0.48416(14) 0.0467(9) Uani 1 1 d . . . C15 C 0.14298(19) 0.1245(5) 0.40008(15) 0.0544(9) Uani 1 1 d . . . H15 H 0.1491 0.0267 0.3717 0.065 Uiso 1 1 calc R . . C30 C 0.5737(2) -0.2954(6) 0.67978(16) 0.0581(10) Uani 1 1 d . . . C19 C 0.3415(2) -0.2369(6) 0.57126(15) 0.0583(10) Uani 1 1 d . . . H19 H 0.3730 -0.2285 0.6124 0.070 Uiso 1 1 calc R . . C21 C 0.3009(2) -0.4166(5) 0.47584(14) 0.0579(10) Uani 1 1 d . . . H21 H 0.3046 -0.5320 0.4522 0.069 Uiso 1 1 calc R . . C18 C 0.28490(19) -0.0818(5) 0.54547(14) 0.0557(10) Uani 1 1 d . . . H18 H 0.2789 0.0291 0.5699 0.067 Uiso 1 1 calc R . . C22 C 0.2447(2) -0.2586(6) 0.45022(15) 0.0570(10) Uani 1 1 d . . . H22 H 0.2119 -0.2693 0.4095 0.068 Uiso 1 1 calc R . . C6 C -0.0219(2) 0.5508(6) 0.37349(15) 0.0580(10) Uani 1 1 d . . . C10 C 0.1805(2) 0.3826(6) 0.30842(15) 0.0627(11) Uani 1 1 d . . . H10 H 0.2119 0.2640 0.3227 0.075 Uiso 1 1 calc R . . C11 C 0.1997(2) 0.5035(7) 0.26602(18) 0.0785(13) Uani 1 1 d . . . H11 H 0.2437 0.4669 0.2513 0.094 Uiso 1 1 calc R . . C13 C 0.0911(2) 0.7416(6) 0.26618(16) 0.0675(11) Uani 1 1 d . . . H13 H 0.0623 0.8640 0.2521 0.081 Uiso 1 1 calc R . . C25 C 0.5353(2) -0.3510(7) 0.61860(17) 0.0646(11) Uani 1 1 d . . . C28 C 0.6337(2) 0.0098(7) 0.6450(2) 0.0807(13) Uani 1 1 d . . . H28 H 0.6670 0.1280 0.6533 0.097 Uiso 1 1 calc R . . C26 C 0.5463(2) -0.2260(7) 0.57338(18) 0.0709(12) Uani 1 1 d . . . H26 H 0.5202 -0.2612 0.5326 0.085 Uiso 1 1 calc R . . C2 C -0.0086(2) 0.2314(7) 0.43283(16) 0.0738(12) Uani 1 1 d . . . H2 H 0.0185 0.1071 0.4470 0.089 Uiso 1 1 calc R . . C29 C 0.6227(2) -0.1139(6) 0.69473(17) 0.0624(10) Uani 1 1 d . . . C24 C 0.4879(2) -0.5477(6) 0.60230(16) 0.0708(11) Uani 1 1 d . . . H24 H 0.5145 -0.6678 0.6210 0.085 Uiso 1 1 calc R . . C23 C 0.4111(2) -0.5712(6) 0.56363(14) 0.0613(10) Uani 1 1 d . . . H23 H 0.3934 -0.7068 0.5529 0.074 Uiso 1 1 calc R . . C5 C -0.0928(2) 0.6003(7) 0.39239(17) 0.0745(12) Uani 1 1 d . . . H5 H -0.1215 0.7233 0.3790 0.089 Uiso 1 1 calc R . . C12 C 0.1532(2) 0.6850(7) 0.24400(16) 0.0778(13) Uani 1 1 d . . . H12 H 0.1656 0.7655 0.2140 0.093 Uiso 1 1 calc R . . C32 C 0.6018(3) -0.3537(8) 0.78860(18) 0.0865(14) Uani 1 1 d . . . H32 H 0.5944 -0.4333 0.8207 0.104 Uiso 1 1 calc R . . C31 C 0.5642(2) -0.4150(7) 0.72989(17) 0.0770(12) Uani 1 1 d . . . H31 H 0.5321 -0.5353 0.7223 0.092 Uiso 1 1 calc R . . C27 C 0.5952(2) -0.0473(7) 0.58600(19) 0.0783(12) Uani 1 1 d . . . H27 H 0.6014 0.0333 0.5538 0.094 Uiso 1 1 calc R . . C34 C 0.6612(2) -0.0583(8) 0.7560(2) 0.0922(14) Uani 1 1 d . . . H34 H 0.6941 0.0604 0.7649 0.111 Uiso 1 1 calc R . . C4 C -0.1192(3) 0.4717(9) 0.42950(19) 0.0881(15) Uani 1 1 d . . . H4 H -0.1652 0.5069 0.4420 0.106 Uiso 1 1 calc R . . C3 C -0.0769(3) 0.2847(8) 0.44911(18) 0.0907(15) Uani 1 1 d . . . H3 H -0.0961 0.1952 0.4739 0.109 Uiso 1 1 calc R . . C33 C 0.6510(3) -0.1754(9) 0.8027(2) 0.0969(16) Uani 1 1 d . . . H33 H 0.6764 -0.1377 0.8434 0.116 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 C9 0.0384(17) 0.042(2) 0.0515(19) -0.0001(18) 0.0034(15) -0.0020(17) C14 0.0451(19) 0.043(2) 0.0506(19) -0.0026(17) 0.0042(16) -0.0005(18) C1 0.048(2) 0.051(3) 0.051(2) -0.0036(18) 0.0100(17) -0.006(2) C7 0.052(2) 0.046(3) 0.069(2) -0.008(2) 0.0017(19) 0.010(2) C8 0.0428(19) 0.047(3) 0.055(2) 0.0012(19) -0.0012(16) -0.0027(18) C16 0.0464(19) 0.048(2) 0.059(2) 0.0013(18) 0.0102(16) 0.0054(18) C20 0.050(2) 0.042(2) 0.058(2) 0.0026(19) 0.0140(17) -0.0019(18) C17 0.0446(18) 0.041(2) 0.0529(19) -0.0010(18) 0.0125(16) -0.0028(17) C15 0.054(2) 0.043(2) 0.063(2) -0.0042(18) 0.0146(17) -0.0035(18) C30 0.046(2) 0.066(3) 0.062(2) 0.000(2) 0.0161(18) 0.013(2) C19 0.058(2) 0.057(3) 0.055(2) -0.003(2) 0.0088(17) 0.006(2) C21 0.064(2) 0.042(2) 0.062(2) -0.0101(19) 0.0098(18) -0.0014(19) C18 0.055(2) 0.052(3) 0.059(2) -0.0063(19) 0.0146(17) 0.0055(19) C22 0.059(2) 0.051(3) 0.052(2) -0.0024(19) 0.0035(17) -0.0037(19) C6 0.050(2) 0.065(3) 0.053(2) -0.012(2) 0.0070(18) 0.003(2) C10 0.053(2) 0.065(3) 0.067(2) 0.008(2) 0.0133(18) 0.006(2) C11 0.055(2) 0.097(4) 0.084(3) 0.018(3) 0.023(2) 0.005(2) C13 0.056(2) 0.064(3) 0.073(3) 0.017(2) 0.005(2) -0.003(2) C25 0.055(2) 0.066(3) 0.070(3) 0.000(2) 0.015(2) 0.011(2) C28 0.058(2) 0.081(4) 0.104(3) 0.007(3) 0.026(2) 0.008(2) C26 0.063(2) 0.080(4) 0.073(3) 0.011(3) 0.025(2) 0.013(2) C2 0.052(2) 0.090(4) 0.080(3) 0.017(2) 0.021(2) 0.003(2) C29 0.048(2) 0.071(3) 0.065(2) -0.004(2) 0.0112(18) 0.010(2) C24 0.074(3) 0.063(3) 0.069(2) -0.004(2) 0.012(2) 0.018(2) C23 0.071(2) 0.045(3) 0.064(2) -0.0015(19) 0.0145(19) 0.005(2) C5 0.063(3) 0.077(4) 0.080(3) -0.019(3) 0.016(2) 0.015(2) C12 0.061(2) 0.095(4) 0.074(3) 0.030(2) 0.015(2) -0.010(3) C32 0.081(3) 0.109(4) 0.065(3) 0.008(3) 0.015(2) -0.005(3) C31 0.066(2) 0.093(4) 0.069(3) 0.014(3) 0.015(2) 0.012(2) C27 0.065(3) 0.085(4) 0.087(3) 0.021(3) 0.027(2) 0.009(3) C34 0.068(3) 0.112(4) 0.095(3) -0.022(3) 0.021(3) -0.002(3) C4 0.069(3) 0.120(5) 0.084(3) -0.014(3) 0.036(2) 0.007(3) C3 0.072(3) 0.116(5) 0.090(3) 0.022(3) 0.033(3) 0.003(3) C33 0.085(3) 0.131(5) 0.075(3) -0.003(3) 0.024(3) -0.004(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 C9 C14 1.409(4) . ? C9 C8 1.430(4) . ? C9 C10 1.422(4) . ? C14 C1 1.407(4) . ? C14 C15 1.477(4) . ? C1 C6 1.429(4) . ? C1 C2 1.419(4) . ? C7 H7 0.9300 . ? C7 C8 1.386(4) . ? C7 C6 1.380(4) . ? C8 C13 1.416(4) . ? C16 H16 0.9300 . ? C16 C17 1.458(4) . ? C16 C15 1.314(4) . ? C20 C19 1.377(4) . ? C20 C21 1.384(4) . ? C20 C23 1.482(4) . ? C17 C18 1.390(4) . ? C17 C22 1.379(4) . ? C15 H15 0.9300 . ? C30 C25 1.396(4) . ? C30 C29 1.412(5) . ? C30 C31 1.425(5) . ? C19 H19 0.9300 . ? C19 C18 1.384(4) . ? C21 H21 0.9300 . ? C21 C22 1.392(4) . ? C18 H18 0.9300 . ? C22 H22 0.9300 . ? C6 C5 1.423(5) . ? C10 H10 0.9300 . ? C10 C11 1.353(4) . ? C11 H11 0.9300 . ? C11 C12 1.413(5) . ? C13 H13 0.9300 . ? C13 C12 1.341(5) . ? C25 C26 1.363(5) . ? C25 C24 1.483(5) . ? C28 H28 0.9300 . ? C28 C29 1.440(5) . ? C28 C27 1.358(5) . ? C26 H26 0.9300 . ? C26 C27 1.393(5) . ? C2 H2 0.9300 . ? C2 C3 1.354(5) . ? C29 C34 1.399(5) . ? C24 H24 0.9300 . ? C24 C23 1.339(4) . ? C23 H23 0.9300 . ? C5 H5 0.9300 . ? C5 C4 1.350(5) . ? C12 H12 0.9300 . ? C32 H32 0.9300 . ? C32 C31 1.356(5) . ? C32 C33 1.396(6) . ? C31 H31 0.9300 . ? C27 H27 0.9300 . ? C34 H34 0.9300 . ? C34 C33 1.355(5) . ? C4 H4 0.9300 . ? C4 C3 1.402(6) . ? C3 H3 0.9300 . ? C33 H33 0.9300 . ? 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 C14 C9 C8 119.5(3) . . ? C14 C9 C10 122.5(3) . . ? C10 C9 C8 118.0(3) . . ? C9 C14 C15 118.7(3) . . ? C1 C14 C9 119.7(3) . . ? C1 C14 C15 121.6(3) . . ? C14 C1 C6 120.1(3) . . ? C14 C1 C2 122.5(3) . . ? C2 C1 C6 117.4(3) . . ? C8 C7 H7 118.8 . . ? C6 C7 H7 118.8 . . ? C6 C7 C8 122.4(3) . . ? C7 C8 C9 119.2(3) . . ? C7 C8 C13 122.5(3) . . ? C13 C8 C9 118.2(3) . . ? C17 C16 H16 116.1 . . ? C15 C16 H16 116.1 . . ? C15 C16 C17 127.8(3) . . ? C19 C20 C21 118.7(3) . . ? C19 C20 C23 120.4(3) . . ? C21 C20 C23 120.8(3) . . ? C18 C17 C16 120.0(3) . . ? C22 C17 C16 122.8(3) . . ? C22 C17 C18 117.2(3) . . ? C14 C15 H15 116.8 . . ? C16 C15 C14 126.4(3) . . ? C16 C15 H15 116.8 . . ? C25 C30 C29 121.0(4) . . ? C25 C30 C31 122.1(4) . . ? C29 C30 C31 116.8(4) . . ? C20 C19 H19 120.0 . . ? C20 C19 C18 120.1(3) . . ? C18 C19 H19 120.0 . . ? C20 C21 H21 119.7 . . ? C20 C21 C22 120.6(3) . . ? C22 C21 H21 119.7 . . ? C17 C18 H18 119.0 . . ? C19 C18 C17 122.1(3) . . ? C19 C18 H18 119.0 . . ? C17 C22 C21 121.2(3) . . ? C17 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C7 C6 C1 118.8(3) . . ? C7 C6 C5 121.7(4) . . ? C5 C6 C1 119.3(4) . . ? C9 C10 H10 119.3 . . ? C11 C10 C9 121.4(3) . . ? C11 C10 H10 119.3 . . ? C10 C11 H11 119.9 . . ? C10 C11 C12 120.2(4) . . ? C12 C11 H11 119.9 . . ? C8 C13 H13 119.1 . . ? C12 C13 C8 121.9(4) . . ? C12 C13 H13 119.1 . . ? C30 C25 C24 121.5(4) . . ? C26 C25 C30 118.4(4) . . ? C26 C25 C24 120.0(4) . . ? C29 C28 H28 120.2 . . ? C27 C28 H28 120.2 . . ? C27 C28 C29 119.6(4) . . ? C25 C26 H26 118.8 . . ? C25 C26 C27 122.5(4) . . ? C27 C26 H26 118.8 . . ? C1 C2 H2 119.5 . . ? C3 C2 C1 121.1(4) . . ? C3 C2 H2 119.5 . . ? C30 C29 C28 118.1(4) . . ? C34 C29 C30 121.0(4) . . ? C34 C29 C28 120.9(4) . . ? C25 C24 H24 116.4 . . ? C23 C24 C25 127.1(3) . . ? C23 C24 H24 116.4 . . ? C20 C23 H23 116.7 . . ? C24 C23 C20 126.7(3) . . ? C24 C23 H23 116.7 . . ? C6 C5 H5 119.5 . . ? C4 C5 C6 121.1(4) . . ? C4 C5 H5 119.5 . . ? C11 C12 H12 119.9 . . ? C13 C12 C11 120.2(4) . . ? C13 C12 H12 119.9 . . ? C31 C32 H32 118.8 . . ? C31 C32 C33 122.4(4) . . ? C33 C32 H32 118.8 . . ? C30 C31 H31 119.9 . . ? C32 C31 C30 120.1(4) . . ? C32 C31 H31 119.9 . . ? C28 C27 C26 120.4(4) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? C29 C34 H34 119.6 . . ? C33 C34 C29 120.7(5) . . ? C33 C34 H34 119.6 . . ? C5 C4 H4 120.2 . . ? C5 C4 C3 119.6(4) . . ? C3 C4 H4 120.2 . . ? C2 C3 C4 121.5(4) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C32 C33 H33 120.6 . . ? C34 C33 C32 118.9(5) . . ? C34 C33 H33 120.6 . . ? 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 C9 C14 C1 C6 -4.8(4) . . . . ? C9 C14 C1 C2 172.7(3) . . . . ? C9 C14 C15 C16 123.2(4) . . . . ? C9 C8 C13 C12 0.3(5) . . . . ? C9 C10 C11 C12 0.4(6) . . . . ? C14 C9 C8 C7 -0.8(4) . . . . ? C14 C9 C8 C13 -179.6(3) . . . . ? C14 C9 C10 C11 179.3(3) . . . . ? C14 C1 C6 C7 2.2(5) . . . . ? C14 C1 C6 C5 178.7(3) . . . . ? C14 C1 C2 C3 -178.0(3) . . . . ? C1 C14 C15 C16 -56.2(5) . . . . ? C1 C6 C5 C4 -0.4(5) . . . . ? C1 C2 C3 C4 -0.8(6) . . . . ? C7 C8 C13 C12 -178.5(3) . . . . ? C7 C6 C5 C4 176.0(3) . . . . ? C8 C9 C14 C1 4.1(4) . . . . ? C8 C9 C14 C15 -175.4(3) . . . . ? C8 C9 C10 C11 -2.2(5) . . . . ? C8 C7 C6 C1 1.2(5) . . . . ? C8 C7 C6 C5 -175.2(3) . . . . ? C8 C13 C12 C11 -2.1(6) . . . . ? C16 C17 C18 C19 -177.1(3) . . . . ? C16 C17 C22 C21 177.8(3) . . . . ? C20 C19 C18 C17 -0.4(5) . . . . ? C20 C21 C22 C17 -0.9(5) . . . . ? C17 C16 C15 C14 -175.2(3) . . . . ? C15 C14 C1 C6 174.7(3) . . . . ? C15 C14 C1 C2 -7.8(5) . . . . ? C15 C16 C17 C18 166.6(3) . . . . ? C15 C16 C17 C22 -13.5(5) . . . . ? C30 C25 C26 C27 1.0(5) . . . . ? C30 C25 C24 C23 130.1(4) . . . . ? C30 C29 C34 C33 -1.3(6) . . . . ? C19 C20 C21 C22 3.5(5) . . . . ? C19 C20 C23 C24 -42.2(5) . . . . ? C21 C20 C19 C18 -2.9(5) . . . . ? C21 C20 C23 C24 141.4(4) . . . . ? C18 C17 C22 C21 -2.4(5) . . . . ? C22 C17 C18 C19 3.0(5) . . . . ? C6 C1 C2 C3 -0.5(5) . . . . ? C6 C7 C8 C9 -1.8(5) . . . . ? C6 C7 C8 C13 176.9(3) . . . . ? C6 C5 C4 C3 -0.9(6) . . . . ? C10 C9 C14 C1 -177.4(3) . . . . ? C10 C9 C14 C15 3.1(4) . . . . ? C10 C9 C8 C7 -179.4(3) . . . . ? C10 C9 C8 C13 1.9(4) . . . . ? C10 C11 C12 C13 1.8(6) . . . . ? C25 C30 C29 C28 -1.4(5) . . . . ? C25 C30 C29 C34 -179.9(3) . . . . ? C25 C30 C31 C32 -179.2(3) . . . . ? C25 C26 C27 C28 -0.5(6) . . . . ? C25 C24 C23 C20 -10.4(6) . . . . ? C28 C29 C34 C33 -179.7(4) . . . . ? C26 C25 C24 C23 -53.7(6) . . . . ? C2 C1 C6 C7 -175.4(3) . . . . ? C2 C1 C6 C5 1.0(4) . . . . ? C29 C30 C25 C26 0.0(5) . . . . ? C29 C30 C25 C24 176.2(3) . . . . ? C29 C30 C31 C32 -0.4(5) . . . . ? C29 C28 C27 C26 -1.0(6) . . . . ? C29 C34 C33 C32 0.4(7) . . . . ? C24 C25 C26 C27 -175.3(3) . . . . ? C23 C20 C19 C18 -179.3(3) . . . . ? C23 C20 C21 C22 180.0(3) . . . . ? C5 C4 C3 C2 1.5(7) . . . . ? C31 C30 C25 C26 178.8(3) . . . . ? C31 C30 C25 C24 -5.0(5) . . . . ? C31 C30 C29 C28 179.8(3) . . . . ? C31 C30 C29 C34 1.3(5) . . . . ? C31 C32 C33 C34 0.5(7) . . . . ? C27 C28 C29 C30 1.9(5) . . . . ? C27 C28 C29 C34 -179.6(3) . . . . ? C33 C32 C31 C30 -0.5(6) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 860990' ####################################################################### # # 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_111117b_lyx_03_55TRANS #TrackingRef '9231_web_deposit_cif_file_1_YexinLi_1327470674.TTNAB.cif' _audit_creation_date 2011-05-25 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C34 H24' _chemical_formula_sum 'C34 H24' _chemical_formula_weight 432.53 _chemical_melting_point ? _chemical_oxdiff_formula 'C H' 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.7869(7) _cell_length_b 6.0629(3) _cell_length_c 25.6359(10) _cell_angle_alpha 90.00 _cell_angle_beta 107.102(5) _cell_angle_gamma 90.00 _cell_volume 2345.24(17) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3207 _cell_measurement_temperature 291.15 _cell_measurement_theta_max 28.8564 _cell_measurement_theta_min 3.1598 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.92192 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 912 _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.07 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0440 _diffrn_reflns_av_unetI/netI 0.0388 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 18229 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.17 _diffrn_ambient_temperature 291.15 _diffrn_detector_area_resol_mean 16.0355 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -13.00 87.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 17.1176 77.0000 -180.0000 100 #__ type_ start__ end____ width___ exp.time_ 2 omega -45.00 43.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 17.1176 -77.0000 60.0000 88 #__ type_ start__ end____ width___ exp.time_ 3 omega -54.00 67.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 17.1176 -15.0000 -126.0000 121 #__ type_ start__ end____ width___ exp.time_ 4 omega -91.00 -48.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - -19.3051 147.0000 -117.0000 43 #__ type_ start__ end____ width___ exp.time_ 5 omega -9.00 67.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 17.1176 37.0000 60.0000 76 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0002249000 _diffrn_orient_matrix_UB_12 -0.1154601000 _diffrn_orient_matrix_UB_13 -0.0044005000 _diffrn_orient_matrix_UB_21 -0.0426372000 _diffrn_orient_matrix_UB_22 -0.0084219000 _diffrn_orient_matrix_UB_23 0.0037668000 _diffrn_orient_matrix_UB_31 -0.0198106000 _diffrn_orient_matrix_UB_32 0.0167866000 _diffrn_orient_matrix_UB_33 -0.0283618000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3035 _reflns_number_total 4800 _reflns_odcompleteness_completeness 99.70 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.159 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.031 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 307 _refine_ls_number_reflns 4800 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0934 _refine_ls_R_factor_gt 0.0530 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+0.2944P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1104 _refine_ls_wR_factor_ref 0.1298 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.74337(11) 0.5154(3) 0.15549(6) 0.0431(4) Uani 1 1 d . . . C9 C 0.59679(12) 0.6217(3) 0.09772(6) 0.0483(4) Uani 1 1 d . . . C6 C 0.70576(12) 0.3248(3) 0.17326(6) 0.0441(4) Uani 1 1 d . . . C10 C 0.68863(12) 0.6585(3) 0.11658(6) 0.0447(4) Uani 1 1 d . . . C8 C 0.55974(12) 0.4306(3) 0.11596(7) 0.0497(5) Uani 1 1 d . . . C7 C 0.61529(12) 0.2870(3) 0.15257(7) 0.0515(5) Uani 1 1 d . . . H7 H 0.5912 0.1616 0.1636 0.062 Uiso 1 1 calc R . . C20 C 0.84959(11) 1.3543(3) -0.03223(7) 0.0487(4) Uani 1 1 d . . . C17 C 0.77378(12) 1.0324(3) 0.02037(6) 0.0466(4) Uani 1 1 d . . . C5 C 0.76273(13) 0.1795(3) 0.21148(7) 0.0539(5) Uani 1 1 d . . . H5 H 0.7390 0.0547 0.2230 0.065 Uiso 1 1 calc R . . C23 C 0.88552(13) 1.5281(3) -0.05929(7) 0.0584(5) Uani 1 1 d . . . H23 H 0.9201 1.6349 -0.0368 0.070 Uiso 1 1 calc R . . C2 C 0.83641(12) 0.5481(3) 0.17757(7) 0.0544(5) Uani 1 1 d . . . H2 H 0.8625 0.6696 0.1663 0.065 Uiso 1 1 calc R . . C30 C 0.88734(11) 1.7238(3) -0.19875(7) 0.0532(5) Uani 1 1 d . . . C4 C 0.85061(14) 0.2194(3) 0.23141(7) 0.0608(5) Uani 1 1 d . . . H4 H 0.8866 0.1224 0.2564 0.073 Uiso 1 1 calc R . . C19 C 0.85084(13) 1.3760(3) 0.02200(7) 0.0599(5) Uani 1 1 d . . . H19 H 0.8774 1.4997 0.0415 0.072 Uiso 1 1 calc R . . C18 C 0.81384(12) 1.2198(3) 0.04762(7) 0.0564(5) Uani 1 1 d . . . H18 H 0.8158 1.2404 0.0839 0.068 Uiso 1 1 calc R . . C15 C 0.73105(12) 0.8421(3) 0.09511(7) 0.0523(5) Uani 1 1 d . . . H15 H 0.7596 0.9505 0.1197 0.063 Uiso 1 1 calc R . . C24 C 0.87406(12) 1.5493(3) -0.11210(7) 0.0565(5) Uani 1 1 d . . . H24 H 0.8405 1.4398 -0.1342 0.068 Uiso 1 1 calc R . . C21 C 0.81085(12) 1.1640(3) -0.05918(7) 0.0544(5) Uani 1 1 d . . . H21 H 0.8102 1.1412 -0.0952 0.065 Uiso 1 1 calc R . . C16 C 0.73152(12) 0.8634(3) 0.04505(7) 0.0548(5) Uani 1 1 d . . . H16 H 0.7005 0.7556 0.0212 0.066 Uiso 1 1 calc R . . C3 C 0.88794(13) 0.4075(3) 0.21444(8) 0.0612(5) Uani 1 1 d . . . H3 H 0.9483 0.4350 0.2287 0.073 Uiso 1 1 calc R . . C22 C 0.77357(13) 1.0094(3) -0.03362(7) 0.0574(5) Uani 1 1 d . . . H22 H 0.7473 0.8852 -0.0530 0.069 Uiso 1 1 calc R . . C31 C 0.83840(13) 1.5560(4) -0.23259(8) 0.0648(6) Uani 1 1 d . . . H31 H 0.8148 1.4419 -0.2170 0.078 Uiso 1 1 calc R . . C29 C 0.91978(12) 1.8983(3) -0.22464(8) 0.0596(5) Uani 1 1 d . . . C25 C 0.90752(12) 1.7237(3) -0.14040(7) 0.0534(5) Uani 1 1 d . . . C11 C 0.53689(14) 0.7700(4) 0.06202(7) 0.0668(6) Uani 1 1 d . . . H11 H 0.5591 0.8960 0.0500 0.080 Uiso 1 1 calc R . . C14 C 0.46612(13) 0.3956(4) 0.09637(8) 0.0636(5) Uani 1 1 d . . . H14 H 0.4416 0.2708 0.1073 0.076 Uiso 1 1 calc R . . C26 C 0.95838(13) 1.8931(3) -0.11163(8) 0.0656(6) Uani 1 1 d . . . H26 H 0.9727 1.8931 -0.0738 0.079 Uiso 1 1 calc R . . C27 C 0.98923(14) 2.0656(4) -0.13766(10) 0.0728(6) Uani 1 1 d . . . H27 H 1.0231 2.1783 -0.1171 0.087 Uiso 1 1 calc R . . C34 C 0.90382(14) 1.8937(4) -0.28172(9) 0.0769(7) Uani 1 1 d . . . H34 H 0.9251 2.0080 -0.2985 0.092 Uiso 1 1 calc R . . C28 C 0.96976(14) 2.0684(4) -0.19266(10) 0.0720(6) Uani 1 1 d . . . H28 H 0.9898 2.1845 -0.2096 0.086 Uiso 1 1 calc R . . C12 C 0.44860(15) 0.7318(4) 0.04520(8) 0.0780(7) Uani 1 1 d . . . H12 H 0.4112 0.8325 0.0222 0.094 Uiso 1 1 calc R . . C13 C 0.41257(14) 0.5423(4) 0.06200(8) 0.0741(6) Uani 1 1 d . . . H13 H 0.3518 0.5173 0.0495 0.089 Uiso 1 1 calc R . . C32 C 0.82489(15) 1.5573(4) -0.28775(8) 0.0808(7) Uani 1 1 d . . . H32 H 0.7930 1.4438 -0.3091 0.097 Uiso 1 1 calc R . . C33 C 0.85875(15) 1.7285(5) -0.31232(9) 0.0868(8) Uani 1 1 d . . . H33 H 0.8500 1.7276 -0.3498 0.104 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 C1 0.0524(11) 0.0379(9) 0.0443(9) -0.0021(8) 0.0222(8) 0.0008(8) C9 0.0565(11) 0.0492(11) 0.0415(9) -0.0035(8) 0.0181(8) 0.0043(9) C6 0.0559(11) 0.0369(9) 0.0432(9) -0.0036(8) 0.0203(8) 0.0000(8) C10 0.0560(11) 0.0419(10) 0.0412(9) -0.0017(8) 0.0219(8) 0.0013(9) C8 0.0561(12) 0.0509(11) 0.0445(9) -0.0113(8) 0.0187(9) -0.0039(9) C7 0.0636(12) 0.0416(10) 0.0539(10) -0.0059(8) 0.0245(9) -0.0100(9) C20 0.0472(10) 0.0505(11) 0.0496(10) 0.0061(9) 0.0160(8) 0.0021(9) C17 0.0514(11) 0.0478(11) 0.0433(9) 0.0028(8) 0.0179(8) 0.0005(9) C5 0.0699(13) 0.0411(10) 0.0559(11) 0.0032(9) 0.0262(10) -0.0004(10) C23 0.0614(12) 0.0565(12) 0.0577(11) 0.0036(9) 0.0184(10) -0.0083(10) C2 0.0546(12) 0.0492(11) 0.0651(11) 0.0051(9) 0.0263(10) -0.0006(9) C30 0.0428(10) 0.0558(12) 0.0624(11) 0.0169(10) 0.0176(9) 0.0051(9) C4 0.0658(14) 0.0527(12) 0.0636(12) 0.0096(9) 0.0183(10) 0.0140(10) C19 0.0749(14) 0.0532(12) 0.0497(10) -0.0024(9) 0.0154(10) -0.0129(10) C18 0.0711(13) 0.0589(12) 0.0406(9) -0.0013(9) 0.0187(9) -0.0043(10) C15 0.0683(12) 0.0418(10) 0.0501(10) -0.0014(8) 0.0227(9) -0.0004(9) C24 0.0584(12) 0.0562(12) 0.0576(11) 0.0061(9) 0.0215(9) -0.0044(10) C21 0.0626(12) 0.0605(12) 0.0448(10) 0.0009(9) 0.0228(9) -0.0007(10) C16 0.0661(13) 0.0536(12) 0.0472(10) -0.0048(9) 0.0206(9) -0.0075(10) C3 0.0500(11) 0.0607(13) 0.0737(13) 0.0067(11) 0.0195(10) 0.0057(10) C22 0.0718(13) 0.0538(12) 0.0505(10) -0.0066(9) 0.0238(10) -0.0108(10) C31 0.0634(13) 0.0698(14) 0.0622(12) 0.0172(11) 0.0197(10) -0.0030(11) C29 0.0424(11) 0.0651(14) 0.0729(13) 0.0249(11) 0.0193(10) 0.0065(10) C25 0.0469(11) 0.0521(11) 0.0653(12) 0.0097(10) 0.0225(9) 0.0040(9) C11 0.0630(14) 0.0746(15) 0.0642(12) 0.0128(11) 0.0211(10) 0.0154(11) C14 0.0582(13) 0.0690(14) 0.0639(12) -0.0187(11) 0.0186(10) -0.0106(11) C26 0.0643(13) 0.0656(14) 0.0719(13) 0.0057(11) 0.0279(11) -0.0041(11) C27 0.0682(14) 0.0599(14) 0.0948(16) 0.0010(12) 0.0307(13) -0.0122(11) C34 0.0576(13) 0.0986(19) 0.0732(14) 0.0408(13) 0.0174(11) -0.0002(13) C28 0.0621(14) 0.0628(14) 0.0948(16) 0.0282(13) 0.0287(12) -0.0008(11) C12 0.0655(15) 0.0941(19) 0.0708(14) 0.0099(13) 0.0147(12) 0.0207(14) C13 0.0516(13) 0.0963(18) 0.0697(14) -0.0186(13) 0.0103(11) 0.0033(13) C32 0.0763(16) 0.0977(18) 0.0624(13) 0.0130(12) 0.0110(11) -0.0135(14) C33 0.0744(16) 0.122(2) 0.0590(13) 0.0274(14) 0.0121(12) -0.0115(16) _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 C6 1.433(2) . ? C1 C10 1.410(2) . ? C1 C2 1.424(2) . ? C9 C10 1.405(2) . ? C9 C8 1.436(2) . ? C9 C11 1.425(3) . ? C6 C7 1.389(2) . ? C6 C5 1.424(2) . ? C10 C15 1.486(2) . ? C8 C7 1.387(2) . ? C8 C14 1.430(2) . ? C7 H7 0.9300 . ? C20 C23 1.465(2) . ? C20 C19 1.391(2) . ? C20 C21 1.390(2) . ? C17 C18 1.385(2) . ? C17 C16 1.464(2) . ? C17 C22 1.390(2) . ? C5 H5 0.9300 . ? C5 C4 1.352(2) . ? C23 H23 0.9300 . ? C23 C24 1.318(2) . ? C2 H2 0.9300 . ? C2 C3 1.353(2) . ? C30 C31 1.411(3) . ? C30 C29 1.422(2) . ? C30 C25 1.435(2) . ? C4 H4 0.9300 . ? C4 C3 1.410(3) . ? C19 H19 0.9300 . ? C19 C18 1.377(2) . ? C18 H18 0.9300 . ? C15 H15 0.9300 . ? C15 C16 1.292(2) . ? C24 H24 0.9300 . ? C24 C25 1.466(2) . ? C21 H21 0.9300 . ? C21 C22 1.371(2) . ? C16 H16 0.9300 . ? C3 H3 0.9300 . ? C22 H22 0.9300 . ? C31 H31 0.9300 . ? C31 C32 1.367(3) . ? C29 C34 1.410(3) . ? C29 C28 1.406(3) . ? C25 C26 1.377(3) . ? C11 H11 0.9300 . ? C11 C12 1.352(3) . ? C14 H14 0.9300 . ? C14 C13 1.358(3) . ? C26 H26 0.9300 . ? C26 C27 1.403(3) . ? C27 H27 0.9300 . ? C27 C28 1.352(3) . ? C34 H34 0.9300 . ? C34 C33 1.340(3) . ? C28 H28 0.9300 . ? C12 H12 0.9300 . ? C12 C13 1.404(3) . ? C13 H13 0.9300 . ? C32 H32 0.9300 . ? C32 C33 1.399(3) . ? C33 H33 0.9300 . ? 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 C6 119.73(16) . . ? C10 C1 C2 122.78(16) . . ? C2 C1 C6 117.47(15) . . ? C10 C9 C8 119.60(16) . . ? C10 C9 C11 122.93(17) . . ? C11 C9 C8 117.45(17) . . ? C7 C6 C1 119.19(16) . . ? C7 C6 C5 122.09(16) . . ? C5 C6 C1 118.72(16) . . ? C1 C10 C15 118.29(16) . . ? C9 C10 C1 120.11(16) . . ? C9 C10 C15 121.57(15) . . ? C7 C8 C9 119.32(17) . . ? C7 C8 C14 121.78(18) . . ? C14 C8 C9 118.90(17) . . ? C6 C7 H7 119.0 . . ? C8 C7 C6 121.94(17) . . ? C8 C7 H7 119.0 . . ? C19 C20 C23 120.77(17) . . ? C21 C20 C23 122.45(15) . . ? C21 C20 C19 116.76(16) . . ? C18 C17 C16 123.67(15) . . ? C18 C17 C22 116.84(16) . . ? C22 C17 C16 119.49(16) . . ? C6 C5 H5 119.3 . . ? C4 C5 C6 121.33(17) . . ? C4 C5 H5 119.3 . . ? C20 C23 H23 116.5 . . ? C24 C23 C20 126.96(18) . . ? C24 C23 H23 116.5 . . ? C1 C2 H2 119.1 . . ? C3 C2 C1 121.87(17) . . ? C3 C2 H2 119.1 . . ? C31 C30 C29 117.18(17) . . ? C31 C30 C25 123.65(16) . . ? C29 C30 C25 119.15(18) . . ? C5 C4 H4 119.9 . . ? C5 C4 C3 120.24(18) . . ? C3 C4 H4 119.9 . . ? C20 C19 H19 119.1 . . ? C18 C19 C20 121.88(17) . . ? C18 C19 H19 119.1 . . ? C17 C18 H18 119.4 . . ? C19 C18 C17 121.23(16) . . ? C19 C18 H18 119.4 . . ? C10 C15 H15 117.4 . . ? C16 C15 C10 125.27(17) . . ? C16 C15 H15 117.4 . . ? C23 C24 H24 115.9 . . ? C23 C24 C25 128.17(18) . . ? C25 C24 H24 115.9 . . ? C20 C21 H21 119.4 . . ? C22 C21 C20 121.16(16) . . ? C22 C21 H21 119.4 . . ? C17 C16 H16 115.3 . . ? C15 C16 C17 129.47(17) . . ? C15 C16 H16 115.3 . . ? C2 C3 C4 120.35(19) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C17 C22 H22 118.9 . . ? C21 C22 C17 122.11(17) . . ? C21 C22 H22 118.9 . . ? C30 C31 H31 119.2 . . ? C32 C31 C30 121.51(19) . . ? C32 C31 H31 119.2 . . ? C34 C29 C30 119.4(2) . . ? C28 C29 C30 119.39(18) . . ? C28 C29 C34 121.20(19) . . ? C30 C25 C24 120.96(17) . . ? C26 C25 C30 118.28(17) . . ? C26 C25 C24 120.75(17) . . ? C9 C11 H11 119.2 . . ? C12 C11 C9 121.6(2) . . ? C12 C11 H11 119.2 . . ? C8 C14 H14 119.6 . . ? C13 C14 C8 120.8(2) . . ? C13 C14 H14 119.6 . . ? C25 C26 H26 119.0 . . ? C25 C26 C27 122.07(19) . . ? C27 C26 H26 119.0 . . ? C26 C27 H27 120.0 . . ? C28 C27 C26 120.1(2) . . ? C28 C27 H27 120.0 . . ? C29 C34 H34 119.2 . . ? C33 C34 C29 121.6(2) . . ? C33 C34 H34 119.2 . . ? C29 C28 H28 119.5 . . ? C27 C28 C29 121.03(19) . . ? C27 C28 H28 119.5 . . ? C11 C12 H12 119.5 . . ? C11 C12 C13 121.0(2) . . ? C13 C12 H12 119.5 . . ? C14 C13 C12 120.3(2) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C31 C32 H32 119.8 . . ? C31 C32 C33 120.4(2) . . ? C33 C32 H32 119.8 . . ? C34 C33 C32 119.9(2) . . ? C34 C33 H33 120.1 . . ? C32 C33 H33 120.1 . . ? 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 C1 C6 C7 C8 -1.3(2) . . . . ? C1 C6 C5 C4 0.6(2) . . . . ? C1 C10 C15 C16 115.5(2) . . . . ? C1 C2 C3 C4 1.3(3) . . . . ? C9 C10 C15 C16 -62.5(2) . . . . ? C9 C8 C7 C6 1.6(2) . . . . ? C9 C8 C14 C13 -1.4(3) . . . . ? C9 C11 C12 C13 -0.6(3) . . . . ? C6 C1 C10 C9 3.8(2) . . . . ? C6 C1 C10 C15 -174.22(13) . . . . ? C6 C1 C2 C3 -0.8(2) . . . . ? C6 C5 C4 C3 -0.1(3) . . . . ? C10 C1 C6 C7 -1.4(2) . . . . ? C10 C1 C6 C5 178.32(14) . . . . ? C10 C1 C2 C3 -179.26(16) . . . . ? C10 C9 C8 C7 0.9(2) . . . . ? C10 C9 C8 C14 180.00(15) . . . . ? C10 C9 C11 C12 -178.98(17) . . . . ? C10 C15 C16 C17 -177.55(17) . . . . ? C8 C9 C10 C1 -3.5(2) . . . . ? C8 C9 C10 C15 174.39(14) . . . . ? C8 C9 C11 C12 -0.9(3) . . . . ? C8 C14 C13 C12 -0.1(3) . . . . ? C7 C6 C5 C4 -179.68(16) . . . . ? C7 C8 C14 C13 177.71(17) . . . . ? C20 C23 C24 C25 178.55(17) . . . . ? C20 C19 C18 C17 0.2(3) . . . . ? C20 C21 C22 C17 -1.1(3) . . . . ? C5 C6 C7 C8 179.01(15) . . . . ? C5 C4 C3 C2 -0.9(3) . . . . ? C23 C20 C19 C18 176.95(18) . . . . ? C23 C20 C21 C22 -176.52(17) . . . . ? C23 C24 C25 C30 -178.84(18) . . . . ? C23 C24 C25 C26 0.4(3) . . . . ? C2 C1 C6 C7 -179.87(15) . . . . ? C2 C1 C6 C5 -0.2(2) . . . . ? C2 C1 C10 C9 -177.81(15) . . . . ? C2 C1 C10 C15 4.2(2) . . . . ? C30 C31 C32 C33 -0.8(3) . . . . ? C30 C29 C34 C33 0.0(3) . . . . ? C30 C29 C28 C27 1.6(3) . . . . ? C30 C25 C26 C27 1.2(3) . . . . ? C19 C20 C23 C24 -166.27(19) . . . . ? C19 C20 C21 C22 1.8(3) . . . . ? C18 C17 C16 C15 -7.9(3) . . . . ? C18 C17 C22 C21 -0.2(3) . . . . ? C24 C25 C26 C27 -178.16(18) . . . . ? C21 C20 C23 C24 12.0(3) . . . . ? C21 C20 C19 C18 -1.4(3) . . . . ? C16 C17 C18 C19 -178.49(17) . . . . ? C16 C17 C22 C21 178.94(17) . . . . ? C22 C17 C18 C19 0.6(3) . . . . ? C22 C17 C16 C15 173.07(19) . . . . ? C31 C30 C29 C34 -1.5(3) . . . . ? C31 C30 C29 C28 -179.31(18) . . . . ? C31 C30 C25 C24 -2.8(3) . . . . ? C31 C30 C25 C26 177.86(19) . . . . ? C31 C32 C33 C34 -0.8(4) . . . . ? C29 C30 C31 C32 1.9(3) . . . . ? C29 C30 C25 C24 178.86(16) . . . . ? C29 C30 C25 C26 -0.4(2) . . . . ? C29 C34 C33 C32 1.2(4) . . . . ? C25 C30 C31 C32 -176.44(18) . . . . ? C25 C30 C29 C34 176.93(17) . . . . ? C25 C30 C29 C28 -0.9(3) . . . . ? C25 C26 C27 C28 -0.5(3) . . . . ? C11 C9 C10 C1 174.53(16) . . . . ? C11 C9 C10 C15 -7.6(2) . . . . ? C11 C9 C8 C7 -177.27(15) . . . . ? C11 C9 C8 C14 1.8(2) . . . . ? C11 C12 C13 C14 1.1(3) . . . . ? C14 C8 C7 C6 -177.54(15) . . . . ? C26 C27 C28 C29 -0.9(3) . . . . ? C34 C29 C28 C27 -176.17(19) . . . . ? C28 C29 C34 C33 177.8(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 860992'