# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_121122_h_12_9_24_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H28' _chemical_formula_sum 'C38 H28' _chemical_formula_weight 484.60 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.3653(9) _cell_length_b 22.7961(12) _cell_length_c 19.7772(14) _cell_angle_alpha 90.00 _cell_angle_beta 98.854(7) _cell_angle_gamma 90.00 _cell_volume 5508.4(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2529 _cell_measurement_theta_min 3.1210 _cell_measurement_theta_max 29.5905 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2048 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9805 _exptl_absorpt_correction_T_max 0.9850 _exptl_absorpt_process_details ; CrysAlis PRO (Agilent Technologies, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22956 _diffrn_reflns_av_R_equivalents 0.0853 _diffrn_reflns_av_sigmaI/netI 0.1345 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 25.35 _reflns_number_total 10046 _reflns_number_gt 4133 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Agilent Technologies, 2011)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0346P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10046 _refine_ls_number_parameters 685 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1892 _refine_ls_R_factor_gt 0.0669 _refine_ls_wR_factor_ref 0.1601 _refine_ls_wR_factor_gt 0.1142 _refine_ls_goodness_of_fit_ref 0.953 _refine_ls_restrained_S_all 0.953 _refine_ls_shift/su_max 0.003 _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 0.0391(3) 0.18328(16) 0.1941(2) 0.0712(12) Uani 1 1 d . . . H1 H 0.0691 0.1563 0.2270 0.085 Uiso 1 1 calc R . . C2 C -0.0539(4) 0.2137(2) 0.2029(3) 0.0957(17) Uani 1 1 d . . . H2 H -0.0863 0.2071 0.2416 0.115 Uiso 1 1 calc R . . C3 C -0.0995(4) 0.2540(3) 0.1548(4) 0.113(2) Uani 1 1 d . . . H3 H -0.1620 0.2746 0.1611 0.136 Uiso 1 1 calc R . . C4 C -0.0523(4) 0.2633(2) 0.0977(3) 0.0998(17) Uani 1 1 d . . . H4 H -0.0830 0.2902 0.0648 0.120 Uiso 1 1 calc R . . C5 C 0.0414(3) 0.23282(17) 0.0887(2) 0.0748(12) Uani 1 1 d . . . H5 H 0.0731 0.2397 0.0497 0.090 Uiso 1 1 calc R . . C6 C 0.0886(3) 0.19251(15) 0.1362(2) 0.0540(10) Uani 1 1 d . . . C7 C 0.1863(3) 0.15847(13) 0.12429(18) 0.0481(9) Uani 1 1 d . . . C8 C 0.1808(3) 0.13034(14) 0.06143(18) 0.0562(9) Uani 1 1 d . . . H8 H 0.1190 0.1357 0.0287 0.067 Uiso 1 1 calc R . . C9 C 0.2639(3) 0.09464(14) 0.0459(2) 0.0600(10) Uani 1 1 d . . . H9 H 0.2585 0.0769 0.0032 0.072 Uiso 1 1 calc R . . C10 C 0.3540(3) 0.08578(14) 0.09398(19) 0.0579(10) Uani 1 1 d . . . H10 H 0.4096 0.0610 0.0846 0.069 Uiso 1 1 calc R . . C11 C 0.3627(3) 0.11359(13) 0.15643(17) 0.0512(9) Uani 1 1 d . . . H11 H 0.4248 0.1075 0.1887 0.061 Uiso 1 1 calc R . . C12 C 0.2804(3) 0.15087(12) 0.17260(17) 0.0432(8) Uani 1 1 d . . . C13 C 0.2977(3) 0.17899(13) 0.24148(17) 0.0457(8) Uani 1 1 d . . . C14 C 0.3391(3) 0.13795(14) 0.29896(18) 0.0552(10) Uani 1 1 d . . . C15 C 0.2825(4) 0.08708(15) 0.3097(2) 0.0803(13) Uani 1 1 d . . . H15 H 0.2157 0.0791 0.2827 0.096 Uiso 1 1 calc R . . C16 C 0.3254(6) 0.04810(19) 0.3606(3) 0.1037(18) Uani 1 1 d . . . H16 H 0.2856 0.0148 0.3682 0.124 Uiso 1 1 calc R . . C17 C 0.4239(6) 0.0575(3) 0.3993(3) 0.109(2) Uani 1 1 d . . . H17 H 0.4525 0.0304 0.4325 0.131 Uiso 1 1 calc R . . C18 C 0.4810(4) 0.1074(3) 0.3889(3) 0.1096(17) Uani 1 1 d . . . H18 H 0.5488 0.1144 0.4153 0.132 Uiso 1 1 calc R . . C19 C 0.4379(4) 0.14728(19) 0.3395(2) 0.0810(13) Uani 1 1 d . . . H19 H 0.4769 0.1813 0.3335 0.097 Uiso 1 1 calc R . . C20 C 0.2852(2) 0.23713(13) 0.25362(16) 0.0424(8) Uani 1 1 d . . . C21 C 0.2815(3) 0.25739(13) 0.32493(16) 0.0443(8) Uani 1 1 d . . . C22 C 0.2055(3) 0.23425(13) 0.36222(19) 0.0585(10) Uani 1 1 d . . . H22 H 0.1566 0.2060 0.3422 0.070 Uiso 1 1 calc R . . C23 C 0.2007(3) 0.25200(15) 0.4279(2) 0.0656(11) Uani 1 1 d . . . H23 H 0.1490 0.2357 0.4519 0.079 Uiso 1 1 calc R . . C24 C 0.2718(3) 0.29382(16) 0.45839(19) 0.0641(11) Uani 1 1 d . . . H24 H 0.2698 0.3054 0.5033 0.077 Uiso 1 1 calc R . . C25 C 0.3459(3) 0.31831(15) 0.4218(2) 0.0656(11) Uani 1 1 d . . . H25 H 0.3944 0.3467 0.4421 0.079 Uiso 1 1 calc R . . C26 C 0.3493(3) 0.30135(14) 0.35535(18) 0.0556(10) Uani 1 1 d . . . H26 H 0.3978 0.3197 0.3306 0.067 Uiso 1 1 calc R . . C27 C 0.2672(3) 0.28305(13) 0.19980(16) 0.0447(8) Uani 1 1 d . . . C28 C 0.1787(3) 0.32126(14) 0.20100(18) 0.0561(10) Uani 1 1 d . . . H28 H 0.1357 0.3174 0.2354 0.067 Uiso 1 1 calc R . . C29 C 0.1540(3) 0.36437(15) 0.1525(2) 0.0738(12) Uani 1 1 d . . . H29 H 0.0942 0.3888 0.1538 0.089 Uiso 1 1 calc R . . C30 C 0.2174(4) 0.37131(17) 0.1024(2) 0.0858(14) Uani 1 1 d . . . H30 H 0.2006 0.4002 0.0693 0.103 Uiso 1 1 calc R . . C31 C 0.3061(4) 0.33538(16) 0.1012(2) 0.0736(12) Uani 1 1 d . . . H31 H 0.3494 0.3410 0.0672 0.088 Uiso 1 1 calc R . . C32 C 0.3336(3) 0.29101(13) 0.14874(17) 0.0503(9) Uani 1 1 d . . . C33 C 0.4335(3) 0.25632(14) 0.1447(2) 0.0547(10) Uani 1 1 d . . . C34 C 0.5167(3) 0.25135(15) 0.2001(2) 0.0625(10) Uani 1 1 d . . . H34 H 0.5091 0.2692 0.2414 0.075 Uiso 1 1 calc R . . C35 C 0.6115(3) 0.22001(17) 0.1944(2) 0.0777(12) Uani 1 1 d . . . H35 H 0.6671 0.2171 0.2317 0.093 Uiso 1 1 calc R . . C36 C 0.6224(4) 0.19355(19) 0.1338(3) 0.0931(16) Uani 1 1 d . . . H36 H 0.6856 0.1724 0.1303 0.112 Uiso 1 1 calc R . . C37 C 0.5418(4) 0.19770(19) 0.0782(3) 0.0905(16) Uani 1 1 d . . . H37 H 0.5497 0.1793 0.0372 0.109 Uiso 1 1 calc R . . C38 C 0.4484(3) 0.22960(15) 0.0837(2) 0.0686(11) Uani 1 1 d . . . H38 H 0.3943 0.2332 0.0457 0.082 Uiso 1 1 calc R . . C39 C 0.5382(3) -0.01045(13) 0.20016(17) 0.0494(9) Uani 1 1 d . . . H39 H 0.5686 0.0179 0.2312 0.059 Uiso 1 1 calc R . . C40 C 0.4447(3) -0.03982(17) 0.2114(2) 0.0654(11) Uani 1 1 d . . . H40 H 0.4123 -0.0311 0.2496 0.079 Uiso 1 1 calc R . . C41 C 0.3995(3) -0.08203(17) 0.1657(2) 0.0691(11) Uani 1 1 d . . . H41 H 0.3370 -0.1021 0.1734 0.083 Uiso 1 1 calc R . . C42 C 0.4463(3) -0.09456(15) 0.1089(2) 0.0649(10) Uani 1 1 d . . . H42 H 0.4155 -0.1229 0.0779 0.078 Uiso 1 1 calc R . . C43 C 0.5395(3) -0.06485(14) 0.09781(18) 0.0533(9) Uani 1 1 d . . . H43 H 0.5707 -0.0734 0.0591 0.064 Uiso 1 1 calc R . . C44 C 0.5873(2) -0.02267(13) 0.14304(16) 0.0425(8) Uani 1 1 d . . . C45 C 0.6844(3) 0.01051(12) 0.12868(16) 0.0382(8) Uani 1 1 d . . . C46 C 0.6822(3) 0.03190(12) 0.06207(17) 0.0464(9) Uani 1 1 d . . . H46 H 0.6221 0.0234 0.0291 0.056 Uiso 1 1 calc R . . C47 C 0.7663(3) 0.06522(14) 0.04378(19) 0.0554(10) Uani 1 1 d . . . H47 H 0.7639 0.0780 -0.0011 0.066 Uiso 1 1 calc R . . C48 C 0.8529(3) 0.07919(13) 0.0924(2) 0.0586(10) Uani 1 1 d . . . H48 H 0.9088 0.1028 0.0811 0.070 Uiso 1 1 calc R . . C49 C 0.8581(3) 0.05866(13) 0.15816(18) 0.0496(9) Uani 1 1 d . . . H49 H 0.9176 0.0689 0.1907 0.060 Uiso 1 1 calc R . . C50 C 0.7761(3) 0.02260(12) 0.17742(17) 0.0398(8) Uani 1 1 d . . . C51 C 0.7915(3) 0.00075(13) 0.24910(16) 0.0431(8) Uani 1 1 d . . . C52 C 0.8218(3) 0.04698(14) 0.30230(18) 0.0546(9) Uani 1 1 d . . . C53 C 0.7591(3) 0.09741(15) 0.3033(2) 0.0740(12) Uani 1 1 d . . . H53 H 0.6968 0.1025 0.2709 0.089 Uiso 1 1 calc R . . C54 C 0.7887(5) 0.13987(18) 0.3519(3) 0.1016(17) Uani 1 1 d . . . H54 H 0.7449 0.1730 0.3525 0.122 Uiso 1 1 calc R . . C55 C 0.8793(6) 0.1347(2) 0.3985(3) 0.123(2) Uani 1 1 d . . . H55 H 0.8980 0.1642 0.4306 0.148 Uiso 1 1 calc R . . C56 C 0.9452(5) 0.0853(2) 0.3988(3) 0.129(2) Uani 1 1 d . . . H56 H 1.0083 0.0812 0.4307 0.154 Uiso 1 1 calc R . . C57 C 0.9142(4) 0.04186(18) 0.3499(2) 0.0923(14) Uani 1 1 d . . . H57 H 0.9575 0.0085 0.3496 0.111 Uiso 1 1 calc R . . C58 C 0.7856(2) -0.05667(13) 0.26650(16) 0.0421(8) Uani 1 1 d . . . C59 C 0.7807(3) -0.07538(13) 0.33817(16) 0.0472(9) Uani 1 1 d . . . C60 C 0.7079(3) -0.05003(15) 0.37567(19) 0.0720(12) Uani 1 1 d . . . H60 H 0.6625 -0.0200 0.3563 0.086 Uiso 1 1 calc R . . C61 C 0.7012(4) -0.06831(19) 0.4411(2) 0.0916(15) Uani 1 1 d . . . H61 H 0.6521 -0.0502 0.4656 0.110 Uiso 1 1 calc R . . C62 C 0.7663(4) -0.11315(19) 0.4709(2) 0.0901(14) Uani 1 1 d . . . H62 H 0.7619 -0.1254 0.5152 0.108 Uiso 1 1 calc R . . C63 C 0.8375(4) -0.13937(17) 0.4339(2) 0.0792(12) Uani 1 1 d . . . H63 H 0.8821 -0.1697 0.4534 0.095 Uiso 1 1 calc R . . C64 C 0.8441(3) -0.12141(14) 0.36822(19) 0.0625(10) Uani 1 1 d . . . H64 H 0.8920 -0.1404 0.3436 0.075 Uiso 1 1 calc R . . C65 C 0.7755(3) -0.10575(12) 0.21563(16) 0.0424(8) Uani 1 1 d . . . C66 C 0.6874(3) -0.14409(13) 0.21427(17) 0.0499(9) Uani 1 1 d . . . H66 H 0.6391 -0.1393 0.2456 0.060 Uiso 1 1 calc R . . C67 C 0.6706(3) -0.18907(14) 0.1671(2) 0.0646(11) Uani 1 1 d . . . H67 H 0.6104 -0.2137 0.1662 0.077 Uiso 1 1 calc R . . C68 C 0.7426(3) -0.19773(14) 0.12138(19) 0.0656(11) Uani 1 1 d . . . H68 H 0.7312 -0.2278 0.0893 0.079 Uiso 1 1 calc R . . C69 C 0.8313(3) -0.16134(14) 0.12399(17) 0.0564(10) Uani 1 1 d . . . H69 H 0.8806 -0.1678 0.0937 0.068 Uiso 1 1 calc R . . C70 C 0.8507(3) -0.11519(12) 0.17008(16) 0.0448(8) Uani 1 1 d . . . C71 C 0.9511(3) -0.07937(13) 0.17019(19) 0.0455(8) Uani 1 1 d . . . C72 C 1.0257(3) -0.07135(14) 0.2288(2) 0.0602(10) Uani 1 1 d . . . H72 H 1.0121 -0.0873 0.2699 0.072 Uiso 1 1 calc R . . C73 C 1.1207(3) -0.03967(17) 0.2268(3) 0.0808(13) Uani 1 1 d . . . H73 H 1.1707 -0.0347 0.2666 0.097 Uiso 1 1 calc R . . C74 C 1.1417(4) -0.01558(18) 0.1668(3) 0.0858(14) Uani 1 1 d . . . H74 H 1.2048 0.0065 0.1662 0.103 Uiso 1 1 calc R . . C75 C 1.0699(4) -0.02387(16) 0.1076(3) 0.0755(12) Uani 1 1 d . . . H75 H 1.0844 -0.0082 0.0665 0.091 Uiso 1 1 calc R . . C76 C 0.9750(3) -0.05612(14) 0.1097(2) 0.0602(10) Uani 1 1 d . . . H76 H 0.9265 -0.0622 0.0695 0.072 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 0.057(3) 0.075(3) 0.086(3) -0.038(2) 0.025(2) -0.018(2) C2 0.053(3) 0.111(4) 0.132(5) -0.066(4) 0.040(3) -0.020(3) C3 0.051(3) 0.115(4) 0.170(7) -0.079(5) 0.007(4) 0.007(3) C4 0.058(3) 0.094(3) 0.135(5) -0.042(3) -0.025(3) 0.024(3) C5 0.055(3) 0.075(3) 0.087(3) -0.030(2) -0.012(2) 0.012(2) C6 0.040(2) 0.053(2) 0.067(3) -0.026(2) 0.005(2) -0.0037(18) C7 0.052(2) 0.0447(19) 0.051(2) -0.0117(18) 0.018(2) -0.0022(17) C8 0.054(2) 0.061(2) 0.054(3) -0.0101(19) 0.007(2) 0.0026(19) C9 0.069(3) 0.057(2) 0.057(3) -0.015(2) 0.019(2) 0.006(2) C10 0.062(3) 0.055(2) 0.060(3) -0.001(2) 0.019(2) 0.017(2) C11 0.063(2) 0.0460(19) 0.047(2) 0.0005(17) 0.014(2) 0.0074(18) C12 0.050(2) 0.0352(17) 0.048(2) -0.0010(16) 0.017(2) -0.0007(16) C13 0.049(2) 0.0437(19) 0.046(2) -0.0012(17) 0.0129(18) -0.0022(17) C14 0.076(3) 0.047(2) 0.046(2) 0.0003(18) 0.023(2) 0.011(2) C15 0.133(4) 0.043(2) 0.064(3) 0.005(2) 0.011(3) -0.009(2) C16 0.181(6) 0.056(3) 0.080(4) 0.015(3) 0.038(4) 0.008(4) C17 0.161(6) 0.104(4) 0.068(4) 0.027(3) 0.036(4) 0.057(4) C18 0.100(4) 0.135(4) 0.089(4) 0.037(4) 0.004(3) 0.034(4) C19 0.075(3) 0.095(3) 0.071(3) 0.024(3) 0.003(3) 0.017(3) C20 0.041(2) 0.0437(19) 0.043(2) -0.0037(17) 0.0092(17) -0.0050(16) C21 0.052(2) 0.0375(18) 0.044(2) -0.0028(16) 0.0078(18) 0.0026(17) C22 0.071(3) 0.048(2) 0.062(3) -0.0076(19) 0.027(2) -0.0094(19) C23 0.096(3) 0.047(2) 0.060(3) 0.003(2) 0.033(2) 0.001(2) C24 0.090(3) 0.058(2) 0.045(2) 0.001(2) 0.014(2) 0.019(2) C25 0.076(3) 0.057(2) 0.061(3) -0.019(2) 0.005(2) -0.005(2) C26 0.059(2) 0.055(2) 0.054(3) -0.0097(19) 0.013(2) -0.0064(19) C27 0.046(2) 0.0406(18) 0.047(2) -0.0091(16) 0.0049(18) -0.0033(17) C28 0.056(2) 0.050(2) 0.062(3) -0.008(2) 0.008(2) 0.0041(19) C29 0.088(3) 0.051(2) 0.078(3) -0.003(2) -0.002(3) 0.021(2) C30 0.126(4) 0.056(3) 0.073(3) 0.013(2) 0.004(3) 0.016(3) C31 0.100(3) 0.060(2) 0.066(3) 0.008(2) 0.026(3) 0.001(2) C32 0.061(2) 0.0411(19) 0.048(2) 0.0042(18) 0.007(2) -0.0048(18) C33 0.058(3) 0.050(2) 0.060(3) 0.004(2) 0.022(2) -0.0108(19) C34 0.062(3) 0.056(2) 0.073(3) -0.001(2) 0.020(2) -0.008(2) C35 0.056(3) 0.081(3) 0.100(4) 0.002(3) 0.021(3) -0.004(2) C36 0.076(4) 0.084(3) 0.129(5) -0.017(3) 0.049(4) -0.002(3) C37 0.096(4) 0.088(3) 0.103(4) -0.026(3) 0.062(4) -0.021(3) C38 0.082(3) 0.074(3) 0.057(3) -0.003(2) 0.034(2) -0.011(2) C39 0.043(2) 0.0497(19) 0.056(2) 0.0061(18) 0.0098(19) 0.0052(17) C40 0.054(3) 0.073(3) 0.073(3) 0.015(2) 0.020(2) 0.012(2) C41 0.049(3) 0.071(3) 0.088(3) 0.027(3) 0.014(2) -0.004(2) C42 0.059(3) 0.065(2) 0.068(3) 0.007(2) -0.001(2) -0.012(2) C43 0.050(2) 0.053(2) 0.055(2) 0.0031(19) 0.0016(19) -0.0025(18) C44 0.042(2) 0.0406(18) 0.045(2) 0.0081(17) 0.0043(18) 0.0031(16) C45 0.046(2) 0.0310(16) 0.039(2) 0.0019(15) 0.0107(18) 0.0010(15) C46 0.050(2) 0.0417(18) 0.047(2) 0.0018(16) 0.0079(18) -0.0045(17) C47 0.064(3) 0.050(2) 0.056(3) 0.0091(19) 0.018(2) -0.0031(19) C48 0.058(3) 0.043(2) 0.078(3) 0.009(2) 0.022(2) -0.0121(18) C49 0.047(2) 0.0398(18) 0.063(3) 0.0029(18) 0.009(2) -0.0042(16) C50 0.044(2) 0.0315(16) 0.045(2) -0.0018(16) 0.0097(18) -0.0024(16) C51 0.046(2) 0.0405(18) 0.042(2) -0.0011(17) 0.0045(17) 0.0006(16) C52 0.069(3) 0.048(2) 0.045(2) -0.0026(18) 0.002(2) -0.007(2) C53 0.107(4) 0.043(2) 0.071(3) -0.009(2) 0.012(3) 0.005(2) C54 0.164(6) 0.056(3) 0.083(4) -0.018(3) 0.016(4) 0.004(3) C55 0.202(7) 0.077(4) 0.085(4) -0.039(3) 0.001(4) -0.016(4) C56 0.147(5) 0.100(4) 0.117(5) -0.041(4) -0.049(4) -0.010(4) C57 0.104(4) 0.073(3) 0.089(4) -0.025(3) -0.019(3) -0.002(3) C58 0.041(2) 0.0439(19) 0.042(2) 0.0004(17) 0.0067(16) 0.0011(16) C59 0.058(2) 0.0433(19) 0.041(2) 0.0017(17) 0.0110(19) 0.0016(17) C60 0.093(3) 0.069(2) 0.060(3) 0.019(2) 0.030(2) 0.021(2) C61 0.117(4) 0.097(3) 0.070(3) 0.020(3) 0.044(3) 0.032(3) C62 0.129(4) 0.091(3) 0.053(3) 0.018(2) 0.025(3) 0.014(3) C63 0.102(4) 0.073(3) 0.061(3) 0.023(2) 0.006(3) 0.014(2) C64 0.080(3) 0.053(2) 0.055(3) 0.0107(19) 0.012(2) 0.015(2) C65 0.047(2) 0.0320(17) 0.047(2) 0.0063(16) 0.0038(18) 0.0045(16) C66 0.053(2) 0.0414(19) 0.056(2) 0.0100(18) 0.0116(19) -0.0016(18) C67 0.072(3) 0.040(2) 0.077(3) 0.010(2) -0.004(2) -0.0157(19) C68 0.100(3) 0.038(2) 0.057(3) -0.0001(18) 0.006(2) -0.010(2) C69 0.076(3) 0.0415(19) 0.053(2) -0.0014(18) 0.016(2) -0.0001(19) C70 0.052(2) 0.0357(18) 0.046(2) 0.0003(16) 0.0031(18) 0.0045(16) C71 0.044(2) 0.0388(18) 0.054(2) -0.0048(18) 0.009(2) 0.0041(17) C72 0.052(3) 0.058(2) 0.069(3) 0.005(2) 0.006(2) 0.0031(19) C73 0.051(3) 0.076(3) 0.110(4) 0.000(3) -0.004(3) -0.006(2) C74 0.055(3) 0.069(3) 0.137(5) 0.000(3) 0.023(3) -0.003(2) C75 0.066(3) 0.069(3) 0.099(4) 0.006(3) 0.038(3) 0.001(2) C76 0.062(3) 0.056(2) 0.066(3) -0.007(2) 0.020(2) -0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.377(5) . ? C1 C6 1.395(4) . ? C1 H1 0.9300 . ? C2 C3 1.379(7) . ? C2 H2 0.9300 . ? C3 C4 1.365(6) . ? C3 H3 0.9300 . ? C4 C5 1.386(5) . ? C4 H4 0.9300 . ? C5 C6 1.379(5) . ? C5 H5 0.9300 . ? C6 C7 1.485(4) . ? C7 C8 1.391(4) . ? C7 C12 1.398(4) . ? C8 C9 1.382(4) . ? C8 H8 0.9300 . ? C9 C10 1.363(5) . ? C9 H9 0.9300 . ? C10 C11 1.378(4) . ? C10 H10 0.9300 . ? C11 C12 1.400(4) . ? C11 H11 0.9300 . ? C12 C13 1.491(4) . ? C13 C20 1.360(4) . ? C13 C14 1.500(4) . ? C14 C19 1.371(5) . ? C14 C15 1.387(4) . ? C15 C16 1.385(6) . ? C15 H15 0.9300 . ? C16 C17 1.352(7) . ? C16 H16 0.9300 . ? C17 C18 1.371(6) . ? C17 H17 0.9300 . ? C18 C19 1.381(5) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C27 1.485(4) . ? C20 C21 1.492(4) . ? C21 C26 1.384(4) . ? C21 C22 1.385(4) . ? C22 C23 1.371(4) . ? C22 H22 0.9300 . ? C23 C24 1.372(5) . ? C23 H23 0.9300 . ? C24 C25 1.370(4) . ? C24 H24 0.9300 . ? C25 C26 1.378(4) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 C28 1.401(4) . ? C27 C32 1.408(4) . ? C28 C29 1.374(5) . ? C28 H28 0.9300 . ? C29 C30 1.364(5) . ? C29 H29 0.9300 . ? C30 C31 1.372(5) . ? C30 H30 0.9300 . ? C31 C32 1.388(5) . ? C31 H31 0.9300 . ? C32 C33 1.478(5) . ? C33 C34 1.387(5) . ? C33 C38 1.389(4) . ? C34 C35 1.391(5) . ? C34 H34 0.9300 . ? C35 C36 1.367(5) . ? C35 H35 0.9300 . ? C36 C37 1.370(6) . ? C36 H36 0.9300 . ? C37 C38 1.383(5) . ? C37 H37 0.9300 . ? C38 H38 0.9300 . ? C39 C40 1.383(4) . ? C39 C44 1.390(4) . ? C39 H39 0.9300 . ? C40 C41 1.378(5) . ? C40 H40 0.9300 . ? C41 C42 1.370(5) . ? C41 H41 0.9300 . ? C42 C43 1.383(4) . ? C42 H42 0.9300 . ? C43 C44 1.383(4) . ? C43 H43 0.9300 . ? C44 C45 1.484(4) . ? C45 C50 1.398(4) . ? C45 C46 1.401(4) . ? C46 C47 1.380(4) . ? C46 H46 0.9300 . ? C47 C48 1.363(5) . ? C47 H47 0.9300 . ? C48 C49 1.374(4) . ? C48 H48 0.9300 . ? C49 C50 1.403(4) . ? C49 H49 0.9300 . ? C50 C51 1.487(4) . ? C51 C58 1.358(4) . ? C51 C52 1.496(4) . ? C52 C57 1.369(5) . ? C52 C53 1.389(4) . ? C53 C54 1.374(5) . ? C53 H53 0.9300 . ? C54 C55 1.342(7) . ? C54 H54 0.9300 . ? C55 C56 1.390(7) . ? C55 H55 0.9300 . ? C56 C57 1.395(6) . ? C56 H56 0.9300 . ? C57 H57 0.9300 . ? C58 C59 1.490(4) . ? C58 C65 1.497(4) . ? C59 C60 1.378(4) . ? C59 C64 1.388(4) . ? C60 C61 1.375(5) . ? C60 H60 0.9300 . ? C61 C62 1.376(5) . ? C61 H61 0.9300 . ? C62 C63 1.366(5) . ? C62 H62 0.9300 . ? C63 C64 1.377(4) . ? C63 H63 0.9300 . ? C64 H64 0.9300 . ? C65 C66 1.393(4) . ? C65 C70 1.408(4) . ? C66 C67 1.380(4) . ? C66 H66 0.9300 . ? C67 C68 1.378(4) . ? C67 H67 0.9300 . ? C68 C69 1.370(4) . ? C68 H68 0.9300 . ? C69 C70 1.389(4) . ? C69 H69 0.9300 . ? C70 C71 1.485(4) . ? C71 C72 1.378(5) . ? C71 C76 1.381(4) . ? C72 C73 1.385(5) . ? C72 H72 0.9300 . ? C73 C74 1.368(5) . ? C73 H73 0.9300 . ? C74 C75 1.369(6) . ? C74 H74 0.9300 . ? C75 C76 1.391(5) . ? C75 H75 0.9300 . ? C76 H76 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 C2 C1 C6 120.5(4) . . ? C2 C1 H1 119.7 . . ? C6 C1 H1 119.7 . . ? C1 C2 C3 120.6(5) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 119.6(5) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 120.0(5) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 121.4(4) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C1 117.9(3) . . ? C5 C6 C7 120.6(3) . . ? C1 C6 C7 121.5(4) . . ? C8 C7 C12 118.3(3) . . ? C8 C7 C6 117.0(3) . . ? C12 C7 C6 124.6(3) . . ? C9 C8 C7 122.3(4) . . ? C9 C8 H8 118.9 . . ? C7 C8 H8 118.9 . . ? C10 C9 C8 119.2(3) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C9 C10 C11 119.9(3) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C12 121.7(3) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C7 C12 C11 118.5(3) . . ? C7 C12 C13 124.0(3) . . ? C11 C12 C13 117.5(3) . . ? C20 C13 C12 125.2(3) . . ? C20 C13 C14 120.6(3) . . ? C12 C13 C14 114.1(3) . . ? C19 C14 C15 117.7(4) . . ? C19 C14 C13 121.0(3) . . ? C15 C14 C13 121.1(4) . . ? C16 C15 C14 120.1(5) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C17 C16 C15 121.4(5) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C16 C17 C18 119.1(5) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? C17 C18 C19 120.0(5) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C14 C19 C18 121.6(4) . . ? C14 C19 H19 119.2 . . ? C18 C19 H19 119.2 . . ? C13 C20 C27 124.7(3) . . ? C13 C20 C21 119.3(3) . . ? C27 C20 C21 115.9(2) . . ? C26 C21 C22 117.4(3) . . ? C26 C21 C20 122.0(3) . . ? C22 C21 C20 120.5(3) . . ? C23 C22 C21 121.6(3) . . ? C23 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? C22 C23 C24 120.2(3) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C25 C24 C23 119.1(3) . . ? C25 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? C24 C25 C26 120.7(3) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C25 C26 C21 120.8(3) . . ? C25 C26 H26 119.6 . . ? C21 C26 H26 119.6 . . ? C28 C27 C32 118.4(3) . . ? C28 C27 C20 117.2(3) . . ? C32 C27 C20 124.4(3) . . ? C29 C28 C27 121.5(3) . . ? C29 C28 H28 119.2 . . ? C27 C28 H28 119.2 . . ? C30 C29 C28 120.0(4) . . ? C30 C29 H29 120.0 . . ? C28 C29 H29 120.0 . . ? C29 C30 C31 119.6(4) . . ? C29 C30 H30 120.2 . . ? C31 C30 H30 120.2 . . ? C30 C31 C32 122.4(4) . . ? C30 C31 H31 118.8 . . ? C32 C31 H31 118.8 . . ? C31 C32 C27 118.1(3) . . ? C31 C32 C33 118.2(3) . . ? C27 C32 C33 123.6(3) . . ? C34 C33 C38 117.9(4) . . ? C34 C33 C32 121.7(3) . . ? C38 C33 C32 120.3(4) . . ? C33 C34 C35 120.7(4) . . ? C33 C34 H34 119.6 . . ? C35 C34 H34 119.6 . . ? C36 C35 C34 119.7(5) . . ? C36 C35 H35 120.2 . . ? C34 C35 H35 120.2 . . ? C35 C36 C37 121.1(4) . . ? C35 C36 H36 119.5 . . ? C37 C36 H36 119.5 . . ? C36 C37 C38 119.0(4) . . ? C36 C37 H37 120.5 . . ? C38 C37 H37 120.5 . . ? C37 C38 C33 121.6(4) . . ? C37 C38 H38 119.2 . . ? C33 C38 H38 119.2 . . ? C40 C39 C44 120.9(3) . . ? C40 C39 H39 119.5 . . ? C44 C39 H39 119.5 . . ? C41 C40 C39 119.8(3) . . ? C41 C40 H40 120.1 . . ? C39 C40 H40 120.1 . . ? C42 C41 C40 120.2(3) . . ? C42 C41 H41 119.9 . . ? C40 C41 H41 119.9 . . ? C41 C42 C43 119.7(4) . . ? C41 C42 H42 120.2 . . ? C43 C42 H42 120.2 . . ? C44 C43 C42 121.5(3) . . ? C44 C43 H43 119.3 . . ? C42 C43 H43 119.3 . . ? C43 C44 C39 117.9(3) . . ? C43 C44 C45 120.6(3) . . ? C39 C44 C45 121.4(3) . . ? C50 C45 C46 118.4(3) . . ? C50 C45 C44 124.3(3) . . ? C46 C45 C44 117.3(3) . . ? C47 C46 C45 122.1(3) . . ? C47 C46 H46 118.9 . . ? C45 C46 H46 118.9 . . ? C48 C47 C46 119.0(3) . . ? C48 C47 H47 120.5 . . ? C46 C47 H47 120.5 . . ? C47 C48 C49 120.4(3) . . ? C47 C48 H48 119.8 . . ? C49 C48 H48 119.8 . . ? C48 C49 C50 121.7(3) . . ? C48 C49 H49 119.1 . . ? C50 C49 H49 119.1 . . ? C45 C50 C49 118.1(3) . . ? C45 C50 C51 124.2(3) . . ? C49 C50 C51 117.6(3) . . ? C58 C51 C50 124.1(3) . . ? C58 C51 C52 121.2(3) . . ? C50 C51 C52 114.6(3) . . ? C57 C52 C53 118.0(4) . . ? C57 C52 C51 121.1(3) . . ? C53 C52 C51 120.8(4) . . ? C54 C53 C52 120.2(4) . . ? C54 C53 H53 119.9 . . ? C52 C53 H53 119.9 . . ? C55 C54 C53 121.6(5) . . ? C55 C54 H54 119.2 . . ? C53 C54 H54 119.2 . . ? C54 C55 C56 120.1(5) . . ? C54 C55 H55 120.0 . . ? C56 C55 H55 120.0 . . ? C55 C56 C57 118.3(5) . . ? C55 C56 H56 120.9 . . ? C57 C56 H56 120.9 . . ? C52 C57 C56 121.8(4) . . ? C52 C57 H57 119.1 . . ? C56 C57 H57 119.1 . . ? C51 C58 C59 121.9(3) . . ? C51 C58 C65 123.5(3) . . ? C59 C58 C65 114.4(2) . . ? C60 C59 C64 117.4(3) . . ? C60 C59 C58 121.2(3) . . ? C64 C59 C58 121.3(3) . . ? C61 C60 C59 121.2(4) . . ? C61 C60 H60 119.4 . . ? C59 C60 H60 119.4 . . ? C60 C61 C62 120.8(4) . . ? C60 C61 H61 119.6 . . ? C62 C61 H61 119.6 . . ? C63 C62 C61 118.7(4) . . ? C63 C62 H62 120.7 . . ? C61 C62 H62 120.7 . . ? C62 C63 C64 120.8(4) . . ? C62 C63 H63 119.6 . . ? C64 C63 H63 119.6 . . ? C63 C64 C59 121.1(3) . . ? C63 C64 H64 119.4 . . ? C59 C64 H64 119.4 . . ? C66 C65 C70 118.9(3) . . ? C66 C65 C58 117.8(3) . . ? C70 C65 C58 123.3(3) . . ? C67 C66 C65 121.0(3) . . ? C67 C66 H66 119.5 . . ? C65 C66 H66 119.5 . . ? C68 C67 C66 120.3(3) . . ? C68 C67 H67 119.8 . . ? C66 C67 H67 119.8 . . ? C69 C68 C67 118.9(3) . . ? C69 C68 H68 120.6 . . ? C67 C68 H68 120.6 . . ? C68 C69 C70 122.7(3) . . ? C68 C69 H69 118.7 . . ? C70 C69 H69 118.7 . . ? C69 C70 C65 118.1(3) . . ? C69 C70 C71 118.5(3) . . ? C65 C70 C71 123.3(3) . . ? C72 C71 C76 118.2(3) . . ? C72 C71 C70 121.7(3) . . ? C76 C71 C70 120.0(3) . . ? C71 C72 C73 120.4(4) . . ? C71 C72 H72 119.8 . . ? C73 C72 H72 119.8 . . ? C74 C73 C72 120.6(4) . . ? C74 C73 H73 119.7 . . ? C72 C73 H73 119.7 . . ? C73 C74 C75 120.1(4) . . ? C73 C74 H74 119.9 . . ? C75 C74 H74 119.9 . . ? C74 C75 C76 119.0(4) . . ? C74 C75 H75 120.5 . . ? C76 C75 H75 120.5 . . ? C71 C76 C75 121.6(4) . . ? C71 C76 H76 119.2 . . ? C75 C76 H76 119.2 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.283 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 955718' ####################################################################### # # 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_121121_h_12_10_11 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H32' _chemical_formula_sum 'C40 H32' _chemical_formula_weight 512.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 9.6300(5) _cell_length_b 9.2473(5) _cell_length_c 33.2387(17) _cell_angle_alpha 90.00 _cell_angle_beta 97.115(5) _cell_angle_gamma 90.00 _cell_volume 2937.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3176 _cell_measurement_theta_min 3.0504 _cell_measurement_theta_max 29.4586 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.159 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9775 _exptl_absorpt_correction_T_max 0.9819 _exptl_absorpt_process_details ; CrysAlis PRO (Agilent Technologies, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14439 _diffrn_reflns_av_R_equivalents 0.0417 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 25.35 _reflns_number_total 5358 _reflns_number_gt 3656 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Agilent Technologies, 2011)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0539P)^2^+0.7357P] 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 5358 _refine_ls_number_parameters 363 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0951 _refine_ls_R_factor_gt 0.0615 _refine_ls_wR_factor_ref 0.1532 _refine_ls_wR_factor_gt 0.1354 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.001 _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 -0.3455(2) -0.0117(3) 0.15955(7) 0.0562(6) Uani 1 1 d . . . H1 H -0.3350 -0.0866 0.1415 0.067 Uiso 1 1 calc R . . C2 C -0.4562(2) -0.0154(3) 0.18271(8) 0.0703(8) Uani 1 1 d . . . H2 H -0.5176 -0.0933 0.1805 0.084 Uiso 1 1 calc R . . C3 C -0.4747(3) 0.0948(4) 0.20862(9) 0.0848(9) Uani 1 1 d . . . H3 H -0.5490 0.0927 0.2240 0.102 Uiso 1 1 calc R . . C4 C -0.3842(3) 0.2081(4) 0.21189(9) 0.0860(9) Uani 1 1 d . . . H4 H -0.3973 0.2835 0.2296 0.103 Uiso 1 1 calc R . . C5 C -0.2726(3) 0.2131(3) 0.18929(8) 0.0690(7) Uani 1 1 d . . . H5 H -0.2123 0.2920 0.1919 0.083 Uiso 1 1 calc R . . C6 C -0.2500(2) 0.1018(2) 0.16288(6) 0.0474(5) Uani 1 1 d . . . C7 C -0.1368(2) 0.1096(2) 0.13607(6) 0.0418(5) Uani 1 1 d . . . C8 C -0.0080(2) 0.1634(2) 0.14808(6) 0.0422(5) Uani 1 1 d . . . C9 C 0.0515(2) 0.1826(2) 0.19138(6) 0.0451(5) Uani 1 1 d . . . C10 C 0.0386(3) 0.0762(3) 0.22000(6) 0.0567(6) Uani 1 1 d . . . H10 H -0.0147 -0.0056 0.2126 0.068 Uiso 1 1 calc R . . C11 C 0.1031(3) 0.0894(3) 0.25922(7) 0.0699(7) Uani 1 1 d . . . H11 H 0.0923 0.0173 0.2781 0.084 Uiso 1 1 calc R . . C12 C 0.1838(3) 0.2093(3) 0.27056(7) 0.0708(7) Uani 1 1 d . . . H12 H 0.2286 0.2178 0.2969 0.085 Uiso 1 1 calc R . . C13 C 0.1971(3) 0.3152(3) 0.24277(7) 0.0648(7) Uani 1 1 d . . . H13 H 0.2498 0.3973 0.2504 0.078 Uiso 1 1 calc R . . C14 C 0.1335(2) 0.3016(3) 0.20364(7) 0.0548(6) Uani 1 1 d . . . H14 H 0.1456 0.3739 0.1849 0.066 Uiso 1 1 calc R . . C15 C -0.1804(2) 0.0622(2) 0.09340(6) 0.0474(5) Uani 1 1 d . . . C16 C -0.2949(2) 0.1316(3) 0.07155(7) 0.0567(6) Uani 1 1 d . . . H16 H -0.3417 0.2031 0.0842 0.068 Uiso 1 1 calc R . . C17 C -0.3401(3) 0.0974(3) 0.03207(8) 0.0719(8) Uani 1 1 d . . . H17 H -0.4157 0.1460 0.0180 0.086 Uiso 1 1 calc R . . C18 C -0.2730(3) -0.0088(4) 0.01345(8) 0.0805(9) Uani 1 1 d . . . H18 H -0.3021 -0.0315 -0.0135 0.097 Uiso 1 1 calc R . . C19 C -0.1626(3) -0.0827(3) 0.03436(8) 0.0759(8) Uani 1 1 d . . . H19 H -0.1194 -0.1561 0.0213 0.091 Uiso 1 1 calc R . . C20 C -0.1137(2) -0.0498(3) 0.07483(7) 0.0556(6) Uani 1 1 d . . . C21 C 0.0031(3) -0.1372(3) 0.09595(7) 0.0581(6) Uani 1 1 d . . . C22 C 0.1152(3) -0.1754(3) 0.07590(9) 0.0801(8) Uani 1 1 d . . . H22 H 0.1181 -0.1439 0.0494 0.096 Uiso 1 1 calc R . . C23 C 0.2231(3) -0.2595(4) 0.09460(11) 0.0913(10) Uani 1 1 d . . . H23 H 0.2959 -0.2852 0.0801 0.110 Uiso 1 1 calc R . . C24 C 0.2263(3) -0.3064(3) 0.13410(11) 0.0785(8) Uani 1 1 d . . . C25 C 0.1145(3) -0.2693(3) 0.15420(9) 0.0675(7) Uani 1 1 d . . . H25 H 0.1124 -0.3001 0.1807 0.081 Uiso 1 1 calc R . . C26 C 0.0054(3) -0.1865(3) 0.13530(8) 0.0601(6) Uani 1 1 d . . . H26 H -0.0688 -0.1634 0.1496 0.072 Uiso 1 1 calc R . . C27 C 0.3455(3) -0.3978(4) 0.15434(12) 0.1047(11) Uani 1 1 d . . . H27A H 0.3460 -0.3941 0.1832 0.157 Uiso 1 1 calc R . . H27B H 0.4327 -0.3612 0.1474 0.157 Uiso 1 1 calc R . . H27C H 0.3335 -0.4961 0.1453 0.157 Uiso 1 1 calc R . . C28 C 0.0946(2) 0.2004(2) 0.11927(6) 0.0427(5) Uani 1 1 d . . . C29 C 0.2247(2) 0.1320(3) 0.12454(7) 0.0536(6) Uani 1 1 d . . . H29 H 0.2419 0.0619 0.1446 0.064 Uiso 1 1 calc R . . C30 C 0.3285(3) 0.1651(3) 0.10103(8) 0.0632(7) Uani 1 1 d . . . H30 H 0.4141 0.1173 0.1051 0.076 Uiso 1 1 calc R . . C31 C 0.3045(3) 0.2690(3) 0.07161(8) 0.0670(7) Uani 1 1 d . . . H31 H 0.3741 0.2928 0.0557 0.080 Uiso 1 1 calc R . . C32 C 0.1769(3) 0.3381(3) 0.06567(7) 0.0633(7) Uani 1 1 d . . . H32 H 0.1614 0.4076 0.0454 0.076 Uiso 1 1 calc R . . C33 C 0.0701(2) 0.3068(2) 0.08917(6) 0.0476(5) Uani 1 1 d . . . C34 C -0.0615(2) 0.3912(2) 0.08108(7) 0.0520(6) Uani 1 1 d . . . C35 C -0.1240(3) 0.4116(3) 0.04168(8) 0.0708(7) Uani 1 1 d . . . H35 H -0.0846 0.3695 0.0204 0.085 Uiso 1 1 calc R . . C36 C -0.2442(3) 0.4938(4) 0.03353(9) 0.0831(9) Uani 1 1 d . . . H36 H -0.2845 0.5051 0.0068 0.100 Uiso 1 1 calc R . . C37 C -0.3054(3) 0.5590(3) 0.06412(10) 0.0778(8) Uani 1 1 d . . . C38 C -0.2434(3) 0.5393(3) 0.10322(9) 0.0715(7) Uani 1 1 d . . . H38 H -0.2831 0.5818 0.1244 0.086 Uiso 1 1 calc R . . C39 C -0.1231(2) 0.4576(3) 0.11170(8) 0.0589(6) Uani 1 1 d . . . H39 H -0.0828 0.4471 0.1384 0.071 Uiso 1 1 calc R . . C40 C -0.4357(3) 0.6507(4) 0.05461(12) 0.1208(14) Uani 1 1 d . . . H40A H -0.4521 0.6686 0.0260 0.181 Uiso 1 1 calc R . . H40B H -0.4231 0.7410 0.0688 0.181 Uiso 1 1 calc R . . H40C H -0.5146 0.6006 0.0630 0.181 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 0.0421(13) 0.0677(15) 0.0580(13) 0.0142(12) 0.0033(11) -0.0007(12) C2 0.0415(14) 0.093(2) 0.0774(17) 0.0248(17) 0.0098(13) -0.0038(14) C3 0.0548(17) 0.123(3) 0.0818(19) 0.019(2) 0.0301(15) 0.0092(19) C4 0.075(2) 0.102(2) 0.088(2) -0.0123(18) 0.0368(16) 0.0137(19) C5 0.0578(16) 0.0756(18) 0.0770(17) -0.0115(15) 0.0222(13) -0.0008(14) C6 0.0372(12) 0.0573(14) 0.0475(12) 0.0045(11) 0.0052(9) 0.0018(10) C7 0.0367(12) 0.0439(12) 0.0455(11) 0.0024(9) 0.0070(9) 0.0003(9) C8 0.0402(12) 0.0419(12) 0.0452(11) 0.0024(9) 0.0081(9) 0.0016(9) C9 0.0385(12) 0.0517(13) 0.0457(11) -0.0017(10) 0.0076(9) -0.0001(10) C10 0.0632(15) 0.0585(14) 0.0483(13) 0.0037(11) 0.0065(11) -0.0057(12) C11 0.0837(19) 0.0752(18) 0.0499(14) 0.0093(13) 0.0049(13) -0.0007(16) C12 0.0759(19) 0.089(2) 0.0453(13) -0.0065(14) -0.0012(12) 0.0047(16) C13 0.0627(16) 0.0723(17) 0.0575(15) -0.0149(14) -0.0007(12) -0.0065(14) C14 0.0563(14) 0.0566(14) 0.0509(13) -0.0005(11) 0.0047(11) -0.0062(12) C15 0.0399(12) 0.0520(13) 0.0505(12) 0.0007(11) 0.0066(10) -0.0075(10) C16 0.0465(14) 0.0676(15) 0.0545(13) 0.0039(12) 0.0009(11) -0.0059(12) C17 0.0632(17) 0.086(2) 0.0629(16) 0.0084(15) -0.0078(13) -0.0062(15) C18 0.081(2) 0.103(2) 0.0543(15) -0.0029(16) -0.0046(15) -0.0198(18) C19 0.078(2) 0.087(2) 0.0635(16) -0.0227(15) 0.0113(15) -0.0137(16) C20 0.0508(14) 0.0624(15) 0.0540(13) -0.0058(12) 0.0089(11) -0.0092(12) C21 0.0567(15) 0.0545(14) 0.0651(15) -0.0152(12) 0.0159(12) -0.0031(12) C22 0.0696(19) 0.093(2) 0.0815(18) -0.0125(16) 0.0263(15) 0.0142(17) C23 0.070(2) 0.098(2) 0.113(3) -0.012(2) 0.0371(18) 0.0197(18) C24 0.0586(17) 0.0634(17) 0.115(2) -0.0077(17) 0.0150(16) 0.0053(14) C25 0.0598(17) 0.0544(15) 0.0890(18) -0.0016(14) 0.0125(14) -0.0014(13) C26 0.0526(15) 0.0527(14) 0.0765(17) -0.0068(13) 0.0147(12) -0.0003(12) C27 0.074(2) 0.080(2) 0.160(3) 0.004(2) 0.014(2) 0.0189(18) C28 0.0364(11) 0.0487(12) 0.0425(11) -0.0036(10) 0.0033(9) -0.0028(10) C29 0.0422(13) 0.0609(14) 0.0574(13) 0.0054(11) 0.0055(10) 0.0027(11) C30 0.0422(13) 0.0759(17) 0.0739(16) 0.0031(14) 0.0168(12) 0.0058(12) C31 0.0502(15) 0.0858(19) 0.0696(15) 0.0084(15) 0.0264(12) 0.0020(14) C32 0.0572(16) 0.0746(17) 0.0610(14) 0.0161(13) 0.0195(12) 0.0029(13) C33 0.0416(12) 0.0560(13) 0.0457(11) 0.0015(11) 0.0081(9) -0.0005(10) C34 0.0459(13) 0.0545(14) 0.0569(13) 0.0112(11) 0.0115(11) -0.0010(11) C35 0.0584(16) 0.095(2) 0.0608(15) 0.0242(14) 0.0156(12) 0.0077(15) C36 0.0542(17) 0.114(2) 0.0810(19) 0.0503(18) 0.0093(14) 0.0092(17) C37 0.0463(15) 0.0789(19) 0.110(2) 0.0391(18) 0.0179(16) 0.0067(14) C38 0.0548(16) 0.0634(16) 0.098(2) 0.0045(15) 0.0186(15) 0.0100(13) C39 0.0514(14) 0.0557(14) 0.0693(15) 0.0032(12) 0.0066(12) 0.0025(12) C40 0.061(2) 0.137(3) 0.168(4) 0.068(3) 0.027(2) 0.038(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.390(3) . ? C1 C2 1.390(3) . ? C1 H1 0.9300 . ? C2 C3 1.360(4) . ? C2 H2 0.9300 . ? C3 C4 1.358(4) . ? C3 H3 0.9300 . ? C4 C5 1.386(4) . ? C4 H4 0.9300 . ? C5 C6 1.387(3) . ? C5 H5 0.9300 . ? C6 C7 1.493(3) . ? C7 C8 1.350(3) . ? C7 C15 1.494(3) . ? C8 C9 1.492(3) . ? C8 C28 1.499(3) . ? C9 C10 1.385(3) . ? C9 C14 1.386(3) . ? C10 C11 1.378(3) . ? C10 H10 0.9300 . ? C11 C12 1.380(4) . ? C11 H11 0.9300 . ? C12 C13 1.363(4) . ? C12 H12 0.9300 . ? C13 C14 1.373(3) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.400(3) . ? C15 C20 1.402(3) . ? C16 C17 1.368(3) . ? C16 H16 0.9300 . ? C17 C18 1.365(4) . ? C17 H17 0.9300 . ? C18 C19 1.378(4) . ? C18 H18 0.9300 . ? C19 C20 1.402(3) . ? C19 H19 0.9300 . ? C20 C21 1.488(3) . ? C21 C26 1.383(3) . ? C21 C22 1.384(3) . ? C22 C23 1.382(4) . ? C22 H22 0.9300 . ? C23 C24 1.380(4) . ? C23 H23 0.9300 . ? C24 C25 1.379(4) . ? C24 C27 1.515(4) . ? C25 C26 1.386(3) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 C29 1.395(3) . ? C28 C33 1.402(3) . ? C29 C30 1.377(3) . ? C29 H29 0.9300 . ? C30 C31 1.370(3) . ? C30 H30 0.9300 . ? C31 C32 1.378(3) . ? C31 H31 0.9300 . ? C32 C33 1.396(3) . ? C32 H32 0.9300 . ? C33 C34 1.484(3) . ? C34 C39 1.383(3) . ? C34 C35 1.385(3) . ? C35 C36 1.383(4) . ? C35 H35 0.9300 . ? C36 C37 1.376(4) . ? C36 H36 0.9300 . ? C37 C38 1.374(4) . ? C37 C40 1.515(4) . ? C38 C39 1.382(3) . ? C38 H38 0.9300 . ? C39 H39 0.9300 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? 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 C6 C1 C2 121.3(3) . . ? C6 C1 H1 119.4 . . ? C2 C1 H1 119.4 . . ? C3 C2 C1 120.1(3) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C4 C3 C2 119.7(3) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 121.0(3) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C4 C5 C6 120.7(3) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C1 117.2(2) . . ? C5 C6 C7 121.7(2) . . ? C1 C6 C7 120.9(2) . . ? C8 C7 C6 123.60(18) . . ? C8 C7 C15 121.91(18) . . ? C6 C7 C15 114.36(17) . . ? C7 C8 C9 123.92(18) . . ? C7 C8 C28 123.34(18) . . ? C9 C8 C28 112.61(17) . . ? C10 C9 C14 117.3(2) . . ? C10 C9 C8 121.41(19) . . ? C14 C9 C8 121.01(19) . . ? C11 C10 C9 121.2(2) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C12 120.2(2) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 119.3(2) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C12 C13 C14 120.5(2) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C13 C14 C9 121.5(2) . . ? C13 C14 H14 119.2 . . ? C9 C14 H14 119.2 . . ? C16 C15 C20 119.0(2) . . ? C16 C15 C7 118.0(2) . . ? C20 C15 C7 123.01(19) . . ? C17 C16 C15 121.9(2) . . ? C17 C16 H16 119.1 . . ? C15 C16 H16 119.1 . . ? C18 C17 C16 119.3(3) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C17 C18 C19 120.5(3) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C18 C19 C20 121.5(3) . . ? C18 C19 H19 119.3 . . ? C20 C19 H19 119.3 . . ? C15 C20 C19 117.7(2) . . ? C15 C20 C21 123.6(2) . . ? C19 C20 C21 118.6(2) . . ? C26 C21 C22 116.7(2) . . ? C26 C21 C20 123.2(2) . . ? C22 C21 C20 120.1(2) . . ? C23 C22 C21 121.0(3) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C24 C23 C22 122.1(3) . . ? C24 C23 H23 118.9 . . ? C22 C23 H23 118.9 . . ? C25 C24 C23 117.2(3) . . ? C25 C24 C27 121.2(3) . . ? C23 C24 C27 121.6(3) . . ? C24 C25 C26 120.8(3) . . ? C24 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? C21 C26 C25 122.2(2) . . ? C21 C26 H26 118.9 . . ? C25 C26 H26 118.9 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C29 C28 C33 118.49(19) . . ? C29 C28 C8 117.98(18) . . ? C33 C28 C8 123.38(18) . . ? C30 C29 C28 122.1(2) . . ? C30 C29 H29 118.9 . . ? C28 C29 H29 118.9 . . ? C31 C30 C29 119.4(2) . . ? C31 C30 H30 120.3 . . ? C29 C30 H30 120.3 . . ? C30 C31 C32 119.8(2) . . ? C30 C31 H31 120.1 . . ? C32 C31 H31 120.1 . . ? C31 C32 C33 122.0(2) . . ? C31 C32 H32 119.0 . . ? C33 C32 H32 119.0 . . ? C32 C33 C28 118.3(2) . . ? C32 C33 C34 117.5(2) . . ? C28 C33 C34 124.25(19) . . ? C39 C34 C35 117.3(2) . . ? C39 C34 C33 122.3(2) . . ? C35 C34 C33 120.3(2) . . ? C36 C35 C34 121.0(3) . . ? C36 C35 H35 119.5 . . ? C34 C35 H35 119.5 . . ? C37 C36 C35 121.4(3) . . ? C37 C36 H36 119.3 . . ? C35 C36 H36 119.3 . . ? C38 C37 C36 117.7(2) . . ? C38 C37 C40 121.6(3) . . ? C36 C37 C40 120.7(3) . . ? C37 C38 C39 121.4(3) . . ? C37 C38 H38 119.3 . . ? C39 C38 H38 119.3 . . ? C38 C39 C34 121.1(2) . . ? C38 C39 H39 119.4 . . ? C34 C39 H39 119.4 . . ? C37 C40 H40A 109.5 . . ? C37 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C37 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.185 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.032 _database_code_depnum_ccdc_archive 'CCDC 955719' ####################################################################### # # 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_121204_h_12_11_23_zdjy _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H32 O2' _chemical_formula_weight 544.66 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 ? _symmetry_space_group_name_H-M ? 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 9.3819(3) _cell_length_b 9.2364(5) _cell_length_c 34.2924(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.577(4) _cell_angle_gamma 90.00 _cell_volume 2971.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9769 _exptl_absorpt_correction_T_max 0.9833 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11990 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0418 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 25.35 _reflns_number_total 5418 _reflns_number_gt 3718 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0498P)^2^+0.5471P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5418 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0805 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1278 _refine_ls_wR_factor_gt 0.1068 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.85017(16) -0.18184(18) 0.17505(5) 0.0800(5) Uani 1 1 d . . . O2 O 0.13291(18) 0.8470(2) 0.06877(6) 0.1096(7) Uani 1 1 d . . . C1 C 0.65987(19) 0.5208(2) 0.20156(6) 0.0482(5) Uani 1 1 d . . . H1 H 0.6777 0.5914 0.1829 0.058 Uiso 1 1 calc R . . C2 C 0.7129(2) 0.5384(2) 0.23913(6) 0.0568(6) Uani 1 1 d . . . H2 H 0.7637 0.6215 0.2457 0.068 Uiso 1 1 calc R . . C3 C 0.6904(2) 0.4330(3) 0.26665(6) 0.0627(6) Uani 1 1 d . . . H3 H 0.7274 0.4435 0.2917 0.075 Uiso 1 1 calc R . . C4 C 0.6132(2) 0.3123(2) 0.25692(6) 0.0578(6) Uani 1 1 d . . . H4 H 0.5978 0.2410 0.2755 0.069 Uiso 1 1 calc R . . C5 C 0.5577(2) 0.2953(2) 0.21969(5) 0.0481(5) Uani 1 1 d . . . H5 H 0.5046 0.2132 0.2136 0.058 Uiso 1 1 calc R . . C6 C 0.58071(17) 0.3998(2) 0.19129(5) 0.0393(4) Uani 1 1 d . . . C7 C 0.53385(17) 0.37546(18) 0.14995(5) 0.0362(4) Uani 1 1 d . . . C8 C 0.40654(17) 0.31839(18) 0.13959(5) 0.0366(4) Uani 1 1 d . . . C9 C 0.27922(17) 0.3099(2) 0.16526(5) 0.0401(4) Uani 1 1 d . . . C10 C 0.2483(2) 0.4173(2) 0.19217(6) 0.0544(5) Uani 1 1 d . . . H10 H 0.3103 0.4951 0.1951 0.065 Uiso 1 1 calc R . . C11 C 0.1264(2) 0.4106(3) 0.21476(7) 0.0694(7) Uani 1 1 d . . . H11 H 0.1079 0.4833 0.2328 0.083 Uiso 1 1 calc R . . C12 C 0.0331(2) 0.2968(3) 0.21058(7) 0.0706(7) Uani 1 1 d . . . H12 H -0.0485 0.2925 0.2257 0.085 Uiso 1 1 calc R . . C13 C 0.0607(2) 0.1904(3) 0.18422(7) 0.0598(6) Uani 1 1 d . . . H13 H -0.0021 0.1131 0.1815 0.072 Uiso 1 1 calc R . . C14 C 0.18199(18) 0.1964(2) 0.16128(5) 0.0469(5) Uani 1 1 d . . . H14 H 0.1985 0.1238 0.1431 0.056 Uiso 1 1 calc R . . C15 C 0.38237(17) 0.2628(2) 0.09901(5) 0.0394(4) Uani 1 1 d . . . C16 C 0.27936(18) 0.3300(2) 0.07584(5) 0.0459(5) Uani 1 1 d . . . H16 H 0.2270 0.4064 0.0861 0.055 Uiso 1 1 calc R . . C17 C 0.2533(2) 0.2858(3) 0.03804(6) 0.0571(6) Uani 1 1 d . . . H17 H 0.1847 0.3328 0.0229 0.069 Uiso 1 1 calc R . . C18 C 0.3289(2) 0.1724(3) 0.02285(6) 0.0663(6) Uani 1 1 d . . . H18 H 0.3133 0.1439 -0.0029 0.080 Uiso 1 1 calc R . . C19 C 0.4279(2) 0.1006(3) 0.04565(6) 0.0604(6) Uani 1 1 d . . . H19 H 0.4765 0.0221 0.0352 0.072 Uiso 1 1 calc R . . C20 C 0.45717(19) 0.1429(2) 0.08405(5) 0.0462(5) Uani 1 1 d . . . C21 C 0.5623(2) 0.0577(2) 0.10740(6) 0.0475(5) Uani 1 1 d . . . C22 C 0.5385(2) 0.0204(2) 0.14623(6) 0.0489(5) Uani 1 1 d . . . H22 H 0.4541 0.0493 0.1579 0.059 Uiso 1 1 calc R . . C23 C 0.6359(2) -0.0578(2) 0.16774(6) 0.0544(5) Uani 1 1 d . . . H23 H 0.6180 -0.0789 0.1938 0.065 Uiso 1 1 calc R . . C24 C 0.7598(2) -0.1049(2) 0.15089(7) 0.0592(6) Uani 1 1 d . . . C25 C 0.7869(2) -0.0728(3) 0.11247(7) 0.0690(7) Uani 1 1 d . . . H25 H 0.8701 -0.1051 0.1008 0.083 Uiso 1 1 calc R . . C26 C 0.6879(2) 0.0086(2) 0.09137(6) 0.0625(6) Uani 1 1 d . . . H26 H 0.7071 0.0309 0.0655 0.075 Uiso 1 1 calc R . . C27 C 0.9690(3) -0.2494(4) 0.15856(10) 0.1176(12) Uani 1 1 d . . . H27A H 0.9378 -0.3158 0.1387 0.176 Uiso 1 1 calc R . . H27B H 1.0206 -0.3012 0.1784 0.176 Uiso 1 1 calc R . . H27C H 1.0298 -0.1775 0.1473 0.176 Uiso 1 1 calc R . . C28 C 0.64691(17) 0.4082(2) 0.12087(5) 0.0401(4) Uani 1 1 d . . . C29 C 0.77631(19) 0.3344(2) 0.12446(6) 0.0530(5) Uani 1 1 d . . . H29 H 0.7884 0.2685 0.1447 0.064 Uiso 1 1 calc R . . C30 C 0.8863(2) 0.3561(3) 0.09893(7) 0.0688(7) Uani 1 1 d . . . H30 H 0.9705 0.3039 0.1017 0.083 Uiso 1 1 calc R . . C31 C 0.8711(2) 0.4552(3) 0.06941(7) 0.0804(8) Uani 1 1 d . . . H31 H 0.9447 0.4702 0.0519 0.097 Uiso 1 1 calc R . . C32 C 0.7458(2) 0.5324(3) 0.06587(7) 0.0702(7) Uani 1 1 d . . . H32 H 0.7372 0.6012 0.0462 0.084 Uiso 1 1 calc R . . C33 C 0.63145(19) 0.5106(2) 0.09094(5) 0.0476(5) Uani 1 1 d . . . C34 C 0.5009(2) 0.6005(2) 0.08481(6) 0.0471(5) Uani 1 1 d . . . C35 C 0.4456(2) 0.6214(3) 0.04781(6) 0.0645(6) Uani 1 1 d . . . H35 H 0.4922 0.5800 0.0267 0.077 Uiso 1 1 calc R . . C36 C 0.3232(3) 0.7019(3) 0.04090(8) 0.0753(7) Uani 1 1 d . . . H36 H 0.2873 0.7128 0.0157 0.090 Uiso 1 1 calc R . . C37 C 0.2556(2) 0.7654(3) 0.07199(8) 0.0695(7) Uani 1 1 d . . . C38 C 0.3112(2) 0.7494(3) 0.10894(7) 0.0625(6) Uani 1 1 d . . . H38 H 0.2668 0.7941 0.1299 0.075 Uiso 1 1 calc R . . C39 C 0.4314(2) 0.6684(2) 0.11526(6) 0.0508(5) Uani 1 1 d . . . H39 H 0.4672 0.6587 0.1405 0.061 Uiso 1 1 calc R . . C40 C 0.0699(3) 0.8604(5) 0.03136(11) 0.1498(17) Uani 1 1 d . . . H40A H 0.1386 0.8987 0.0135 0.225 Uiso 1 1 calc R . . H40B H -0.0103 0.9246 0.0327 0.225 Uiso 1 1 calc R . . H40C H 0.0387 0.7669 0.0225 0.225 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 0.0623(9) 0.0781(11) 0.0997(13) 0.0196(10) -0.0026(9) 0.0203(9) O2 0.0651(10) 0.1322(17) 0.1315(17) 0.0535(14) -0.0052(11) 0.0349(11) C1 0.0484(10) 0.0500(12) 0.0461(11) -0.0020(10) -0.0019(9) -0.0039(10) C2 0.0551(12) 0.0603(13) 0.0548(13) -0.0165(12) -0.0066(10) -0.0041(11) C3 0.0644(13) 0.0827(17) 0.0410(12) -0.0123(12) -0.0078(10) 0.0083(13) C4 0.0715(13) 0.0635(14) 0.0384(11) 0.0052(10) 0.0000(10) 0.0030(12) C5 0.0552(11) 0.0481(12) 0.0411(11) 0.0014(9) -0.0003(9) -0.0057(10) C6 0.0363(9) 0.0433(10) 0.0385(10) -0.0021(9) 0.0022(8) 0.0024(8) C7 0.0389(9) 0.0352(9) 0.0345(9) 0.0014(8) 0.0025(8) 0.0036(8) C8 0.0378(9) 0.0373(10) 0.0348(9) 0.0001(8) 0.0017(8) 0.0030(8) C9 0.0359(9) 0.0474(11) 0.0368(10) 0.0037(9) 0.0006(8) 0.0057(9) C10 0.0521(11) 0.0597(13) 0.0516(12) -0.0057(11) 0.0089(10) 0.0074(10) C11 0.0681(14) 0.0811(17) 0.0593(14) -0.0051(13) 0.0205(12) 0.0252(14) C12 0.0457(12) 0.099(2) 0.0672(16) 0.0247(15) 0.0179(11) 0.0147(14) C13 0.0381(11) 0.0777(16) 0.0636(14) 0.0198(13) 0.0011(10) -0.0006(11) C14 0.0393(10) 0.0563(12) 0.0449(11) 0.0057(10) -0.0030(9) 0.0012(9) C15 0.0358(9) 0.0469(11) 0.0356(10) -0.0002(9) 0.0024(8) -0.0033(8) C16 0.0414(10) 0.0552(12) 0.0412(11) 0.0010(9) 0.0026(9) 0.0005(9) C17 0.0541(12) 0.0768(16) 0.0403(11) 0.0046(11) -0.0081(9) 0.0005(12) C18 0.0738(14) 0.0853(17) 0.0396(12) -0.0131(12) -0.0061(11) -0.0016(14) C19 0.0686(13) 0.0682(14) 0.0444(12) -0.0165(11) 0.0017(10) 0.0075(12) C20 0.0459(10) 0.0515(12) 0.0412(11) -0.0052(9) 0.0025(9) 0.0002(9) C21 0.0504(11) 0.0456(11) 0.0465(11) -0.0113(9) 0.0024(9) 0.0041(9) C22 0.0480(11) 0.0470(11) 0.0516(12) -0.0021(10) 0.0043(9) 0.0023(9) C23 0.0549(12) 0.0509(12) 0.0575(13) 0.0056(11) 0.0023(10) 0.0012(10) C24 0.0525(12) 0.0513(12) 0.0739(15) 0.0048(12) -0.0021(11) 0.0023(11) C25 0.0579(13) 0.0679(15) 0.0814(17) -0.0061(14) 0.0138(12) 0.0215(12) C26 0.0637(13) 0.0709(15) 0.0531(13) -0.0067(12) 0.0108(11) 0.0128(12) C27 0.0727(18) 0.132(3) 0.149(3) 0.033(2) 0.0093(18) 0.0508(19) C28 0.0384(9) 0.0458(10) 0.0362(10) -0.0005(9) 0.0034(8) -0.0006(9) C29 0.0421(10) 0.0642(13) 0.0526(12) 0.0095(11) 0.0027(9) 0.0032(10) C30 0.0463(12) 0.0839(17) 0.0766(16) 0.0134(14) 0.0163(11) 0.0145(12) C31 0.0596(14) 0.103(2) 0.0792(17) 0.0233(16) 0.0331(12) 0.0140(14) C32 0.0691(14) 0.0806(16) 0.0613(14) 0.0256(13) 0.0223(12) 0.0090(13) C33 0.0476(11) 0.0542(12) 0.0411(10) 0.0037(10) 0.0087(9) 0.0017(10) C34 0.0493(11) 0.0463(11) 0.0457(11) 0.0060(10) 0.0040(9) 0.0000(9) C35 0.0759(14) 0.0702(15) 0.0475(12) 0.0138(11) -0.0006(11) 0.0039(13) C36 0.0740(15) 0.0882(18) 0.0634(16) 0.0304(15) -0.0174(13) -0.0024(15) C37 0.0522(13) 0.0689(15) 0.0873(18) 0.0276(15) -0.0053(13) 0.0063(12) C38 0.0529(12) 0.0618(13) 0.0727(15) 0.0051(12) 0.0015(11) 0.0100(11) C39 0.0478(11) 0.0511(12) 0.0532(12) 0.0024(10) -0.0055(10) 0.0016(10) C40 0.0793(19) 0.224(4) 0.145(3) 0.106(3) -0.019(2) 0.035(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C24 1.377(2) . ? O1 C27 1.402(3) . ? O2 C37 1.379(3) . ? O2 C40 1.412(3) . ? C1 C6 1.385(3) . ? C1 C2 1.386(3) . ? C1 H1 0.9300 . ? C2 C3 1.374(3) . ? C2 H2 0.9300 . ? C3 C4 1.369(3) . ? C3 H3 0.9300 . ? C4 C5 1.382(3) . ? C4 H4 0.9300 . ? C5 C6 1.390(3) . ? C5 H5 0.9300 . ? C6 C7 1.497(2) . ? C7 C8 1.350(2) . ? C7 C28 1.494(2) . ? C8 C9 1.493(2) . ? C8 C15 1.498(2) . ? C9 C10 1.387(3) . ? C9 C14 1.396(2) . ? C10 C11 1.389(3) . ? C10 H10 0.9300 . ? C11 C12 1.374(3) . ? C11 H11 0.9300 . ? C12 C13 1.362(3) . ? C12 H12 0.9300 . ? C13 C14 1.391(3) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.392(2) . ? C15 C20 1.410(3) . ? C16 C17 1.378(3) . ? C16 H16 0.9300 . ? C17 C18 1.371(3) . ? C17 H17 0.9300 . ? C18 C19 1.378(3) . ? C18 H18 0.9300 . ? C19 C20 1.398(3) . ? C19 H19 0.9300 . ? C20 C21 1.489(3) . ? C21 C26 1.381(3) . ? C21 C22 1.396(3) . ? C22 C23 1.374(3) . ? C22 H22 0.9300 . ? C23 C24 1.374(3) . ? C23 H23 0.9300 . ? C24 C25 1.377(3) . ? C25 C26 1.393(3) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 C29 1.397(2) . ? C28 C33 1.402(3) . ? C29 C30 1.375(3) . ? C29 H29 0.9300 . ? C30 C31 1.371(3) . ? C30 H30 0.9300 . ? C31 C32 1.380(3) . ? C31 H31 0.9300 . ? C32 C33 1.396(3) . ? C32 H32 0.9300 . ? C33 C34 1.493(3) . ? C34 C35 1.379(3) . ? C34 C39 1.386(3) . ? C35 C36 1.387(3) . ? C35 H35 0.9300 . ? C36 C37 1.378(3) . ? C36 H36 0.9300 . ? C37 C38 1.374(3) . ? C38 C39 1.369(3) . ? C38 H38 0.9300 . ? C39 H39 0.9300 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? 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 C24 O1 C27 118.3(2) . . ? C37 O2 C40 117.5(3) . . ? C6 C1 C2 121.20(19) . . ? C6 C1 H1 119.4 . . ? C2 C1 H1 119.4 . . ? C3 C2 C1 119.9(2) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C4 C3 C2 119.62(19) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 120.7(2) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C4 C5 C6 120.57(19) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C1 C6 C5 117.93(17) . . ? C1 C6 C7 120.92(17) . . ? C5 C6 C7 120.87(16) . . ? C8 C7 C28 122.38(15) . . ? C8 C7 C6 123.96(16) . . ? C28 C7 C6 113.45(14) . . ? C7 C8 C9 125.20(15) . . ? C7 C8 C15 120.23(15) . . ? C9 C8 C15 114.52(14) . . ? C10 C9 C14 117.49(17) . . ? C10 C9 C8 121.89(17) . . ? C14 C9 C8 120.52(16) . . ? C9 C10 C11 121.2(2) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C12 C11 C10 120.2(2) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C13 C12 C11 119.7(2) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 120.6(2) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C13 C14 C9 120.8(2) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? C16 C15 C20 119.22(16) . . ? C16 C15 C8 118.35(16) . . ? C20 C15 C8 122.40(15) . . ? C17 C16 C15 121.36(19) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C18 C17 C16 119.74(19) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C17 C18 C19 120.03(19) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C18 C19 C20 121.6(2) . . ? C18 C19 H19 119.2 . . ? C20 C19 H19 119.2 . . ? C19 C20 C15 117.92(17) . . ? C19 C20 C21 118.77(17) . . ? C15 C20 C21 123.29(16) . . ? C26 C21 C22 116.37(19) . . ? C26 C21 C20 121.50(18) . . ? C22 C21 C20 122.12(17) . . ? C23 C22 C21 122.00(19) . . ? C23 C22 H22 119.0 . . ? C21 C22 H22 119.0 . . ? C22 C23 C24 120.1(2) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C23 C24 C25 120.0(2) . . ? C23 C24 O1 115.4(2) . . ? C25 C24 O1 124.6(2) . . ? C24 C25 C26 119.0(2) . . ? C24 C25 H25 120.5 . . ? C26 C25 H25 120.5 . . ? C21 C26 C25 122.5(2) . . ? C21 C26 H26 118.7 . . ? C25 C26 H26 118.7 . . ? O1 C27 H27A 109.5 . . ? O1 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O1 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C29 C28 C33 118.51(17) . . ? C29 C28 C7 117.68(16) . . ? C33 C28 C7 123.79(15) . . ? C30 C29 C28 121.98(19) . . ? C30 C29 H29 119.0 . . ? C28 C29 H29 119.0 . . ? C31 C30 C29 119.7(2) . . ? C31 C30 H30 120.2 . . ? C29 C30 H30 120.2 . . ? C30 C31 C32 119.5(2) . . ? C30 C31 H31 120.3 . . ? C32 C31 H31 120.3 . . ? C31 C32 C33 122.0(2) . . ? C31 C32 H32 119.0 . . ? C33 C32 H32 119.0 . . ? C32 C33 C28 118.28(17) . . ? C32 C33 C34 117.86(17) . . ? C28 C33 C34 123.84(16) . . ? C35 C34 C39 117.02(18) . . ? C35 C34 C33 120.50(19) . . ? C39 C34 C33 122.47(17) . . ? C34 C35 C36 122.4(2) . . ? C34 C35 H35 118.8 . . ? C36 C35 H35 118.8 . . ? C37 C36 C35 118.9(2) . . ? C37 C36 H36 120.6 . . ? C35 C36 H36 120.6 . . ? C38 C37 C36 119.6(2) . . ? C38 C37 O2 116.2(3) . . ? C36 C37 O2 124.1(2) . . ? C39 C38 C37 120.6(2) . . ? C39 C38 H38 119.7 . . ? C37 C38 H38 119.7 . . ? C38 C39 C34 121.40(19) . . ? C38 C39 H39 119.3 . . ? C34 C39 H39 119.3 . . ? O2 C40 H40A 109.5 . . ? O2 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? O2 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.172 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.034 _database_code_depnum_ccdc_archive 'CCDC 955720' ####################################################################### # # 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_121122_h_12_11_10 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H24' _chemical_formula_sum 'C28 H24' _chemical_formula_weight 360.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 7.3760(5) _cell_length_b 16.8413(9) _cell_length_c 8.6153(5) _cell_angle_alpha 90.00 _cell_angle_beta 105.155(6) _cell_angle_gamma 90.00 _cell_volume 1032.98(10) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1285 _cell_measurement_theta_min 2.8553 _cell_measurement_theta_max 29.5590 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.159 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9794 _exptl_absorpt_correction_T_max 0.9852 _exptl_absorpt_process_details ; CrysAlis PRO (Agilent Technologies, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4201 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 25.35 _reflns_number_total 1890 _reflns_number_gt 1209 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Agilent Technologies, 2011)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0862P)^2^+0.2877P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1890 _refine_ls_number_parameters 131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0993 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.1968 _refine_ls_wR_factor_gt 0.1718 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 -0.1618(4) 0.44831(17) 0.3106(3) 0.0631(8) Uani 1 1 d . . . H1AB H -0.1249 0.3939 0.3320 0.095 Uiso 0.839(6) 1 calc PR A 1 H1AC H -0.1676 0.4606 0.2006 0.095 Uiso 0.839(6) 1 calc PR A 1 H1AA H -0.2830 0.4565 0.3295 0.095 Uiso 0.839(6) 1 calc PR A 1 H1BE H -0.1279 0.3948 0.2921 0.095 Uiso 0.161(6) 1 calc PR A 2 H1BF H -0.1227 0.4834 0.2377 0.095 Uiso 0.161(6) 1 calc PR A 2 H1BD H -0.2955 0.4518 0.2934 0.095 Uiso 0.161(6) 1 calc PR A 2 C2 C -0.0194(4) 0.50181(19) 0.4204(4) 0.0478(9) Uani 0.839(6) 1 d P . 1 C3 C 0.0697(4) 0.56449(16) 0.3390(3) 0.0594(7) Uani 1 1 d . . . C4 C 0.0085(5) 0.64270(17) 0.3347(3) 0.0729(8) Uani 1 1 d . A . H4 H -0.0738 0.6573 0.3950 0.087 Uiso 1 1 calc R . . C5 C 0.0680(5) 0.69923(17) 0.2423(4) 0.0764(9) Uani 1 1 d . . . H5 H 0.0264 0.7514 0.2409 0.092 Uiso 1 1 calc R A . C6 C 0.1884(5) 0.67757(19) 0.1528(4) 0.0733(9) Uani 1 1 d . A . H6 H 0.2272 0.7149 0.0888 0.088 Uiso 1 1 calc R . . C7 C 0.2521(4) 0.60053(18) 0.1577(3) 0.0639(8) Uani 1 1 d . . . H7 H 0.3341 0.5866 0.0965 0.077 Uiso 1 1 calc R A . C8 C 0.1969(4) 0.54297(15) 0.2517(3) 0.0528(7) Uani 1 1 d . A . C9 C 0.2673(3) 0.46036(16) 0.2521(3) 0.0532(7) Uani 1 1 d . . . C10 C 0.3521(4) 0.42113(16) 0.3944(3) 0.0573(7) Uani 1 1 d . A . H10 H 0.3633 0.4466 0.4922 0.069 Uiso 1 1 calc R . . C11 C 0.4198(4) 0.34492(17) 0.3926(4) 0.0687(8) Uani 1 1 d . . . H11 H 0.4781 0.3197 0.4888 0.082 Uiso 1 1 calc R A . C12 C 0.4014(5) 0.30606(19) 0.2486(4) 0.0812(10) Uani 1 1 d . A . H12 H 0.4449 0.2543 0.2474 0.097 Uiso 1 1 calc R . . C13 C 0.3189(5) 0.3440(2) 0.1075(4) 0.0867(11) Uani 1 1 d . . . H13 H 0.3066 0.3180 0.0101 0.104 Uiso 1 1 calc R A . C14 C 0.2539(4) 0.42053(19) 0.1090(3) 0.0722(9) Uani 1 1 d . A . H14 H 0.2000 0.4459 0.0120 0.087 Uiso 1 1 calc R . . C2A C -0.063(3) 0.4725(11) 0.487(2) 0.0478(9) Uani 0.161(6) 1 d P . 2 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 0.0627(17) 0.0687(18) 0.0558(14) -0.0052(13) 0.0118(13) -0.0172(14) C2 0.0449(17) 0.051(2) 0.0475(19) -0.0029(15) 0.0116(14) -0.0003(14) C3 0.0617(17) 0.0543(16) 0.0648(15) 0.0117(13) 0.0212(13) 0.0032(13) C4 0.084(2) 0.0628(19) 0.0746(18) 0.0112(15) 0.0260(16) 0.0087(16) C5 0.086(2) 0.0530(17) 0.083(2) 0.0122(15) 0.0090(18) -0.0004(16) C6 0.071(2) 0.074(2) 0.0673(18) 0.0200(15) 0.0041(16) -0.0213(16) C7 0.0593(17) 0.075(2) 0.0561(15) 0.0116(14) 0.0131(13) -0.0123(15) C8 0.0469(14) 0.0591(16) 0.0514(13) 0.0064(12) 0.0108(11) -0.0068(12) C9 0.0401(13) 0.0635(17) 0.0570(14) 0.0037(12) 0.0144(11) -0.0033(12) C10 0.0507(15) 0.0611(17) 0.0596(15) 0.0034(13) 0.0138(12) -0.0040(13) C11 0.0574(18) 0.071(2) 0.0739(18) 0.0110(16) 0.0104(14) 0.0021(15) C12 0.0657(19) 0.071(2) 0.099(2) -0.0127(18) 0.0077(18) 0.0109(16) C13 0.081(2) 0.092(2) 0.077(2) -0.0218(18) 0.0027(17) 0.017(2) C14 0.0638(19) 0.089(2) 0.0574(16) -0.0038(15) 0.0051(13) 0.0110(16) C2A 0.0449(17) 0.051(2) 0.0475(19) -0.0029(15) 0.0116(14) -0.0003(14) _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 1.513(4) . ? C1 C2A 1.554(18) . ? C1 H1AB 0.9600 . ? C1 H1AC 0.9600 . ? C1 H1AA 0.9600 . ? C1 H1BE 0.9600 . ? C1 H1BF 0.9600 . ? C1 H1BD 0.9600 . ? C2 C2 1.327(7) 3_566 ? C2 C3 1.510(4) . ? C3 C4 1.390(4) . ? C3 C8 1.395(4) . ? C3 C2A 1.64(2) 3_566 ? C4 C5 1.384(4) . ? C4 H4 0.9300 . ? C5 C6 1.369(4) . ? C5 H5 0.9300 . ? C6 C7 1.377(4) . ? C6 H6 0.9300 . ? C7 C8 1.391(3) . ? C7 H7 0.9300 . ? C8 C9 1.485(4) . ? C9 C14 1.384(4) . ? C9 C10 1.389(3) . ? C10 C11 1.379(4) . ? C10 H10 0.9300 . ? C11 C12 1.377(4) . ? C11 H11 0.9300 . ? C12 C13 1.367(4) . ? C12 H12 0.9300 . ? C13 C14 1.376(4) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C2A C2A 1.29(4) 3_566 ? C2A C3 1.64(2) 3_566 ? 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 C2A 33.2(7) . . ? C2 C1 H1AB 109.5 . . ? C2A C1 H1AB 91.5 . . ? C2 C1 H1AC 109.5 . . ? C2A C1 H1AC 142.6 . . ? H1AB C1 H1AC 109.5 . . ? C2 C1 H1AA 109.5 . . ? C2A C1 H1AA 90.9 . . ? H1AB C1 H1AA 109.5 . . ? H1AC C1 H1AA 109.5 . . ? C2 C1 H1BE 119.7 . . ? C2A C1 H1BE 109.5 . . ? H1AB C1 H1BE 20.4 . . ? H1AC C1 H1BE 89.2 . . ? H1AA C1 H1BE 117.2 . . ? C2 C1 H1BF 76.4 . . ? C2A C1 H1BF 109.5 . . ? H1AB C1 H1BF 126.5 . . ? H1AC C1 H1BF 33.3 . . ? H1AA C1 H1BF 118.4 . . ? H1BE C1 H1BF 109.5 . . ? C2 C1 H1BD 125.2 . . ? C2A C1 H1BD 109.5 . . ? H1AB C1 H1BD 108.4 . . ? H1AC C1 H1BD 93.2 . . ? H1AA C1 H1BD 18.6 . . ? H1BE C1 H1BD 109.5 . . ? H1BF C1 H1BD 109.5 . . ? C2 C2 C3 120.6(4) 3_566 . ? C2 C2 C1 123.1(4) 3_566 . ? C3 C2 C1 116.2(3) . . ? C4 C3 C8 119.4(2) . . ? C4 C3 C2 119.8(3) . . ? C8 C3 C2 120.3(2) . . ? C4 C3 C2A 107.3(6) . 3_566 ? C8 C3 C2A 125.4(6) . 3_566 ? C2 C3 C2A 35.7(6) . 3_566 ? C5 C4 C3 121.2(3) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C6 C5 C4 119.4(3) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C7 120.0(3) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C6 C7 C8 121.7(3) . . ? C6 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? C7 C8 C3 118.3(3) . . ? C7 C8 C9 119.9(2) . . ? C3 C8 C9 121.8(2) . . ? C14 C9 C10 117.8(3) . . ? C14 C9 C8 120.6(2) . . ? C10 C9 C8 121.6(2) . . ? C11 C10 C9 120.9(3) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C12 C11 C10 120.1(3) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C13 C12 C11 119.7(3) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C14 120.3(3) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C13 C14 C9 121.2(3) . . ? C13 C14 H14 119.4 . . ? C9 C14 H14 119.4 . . ? C2A C2A C1 120(2) 3_566 . ? C2A C2A C3 107.5(19) 3_566 3_566 ? C1 C2A C3 132.5(14) . 3_566 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.286 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.035 _database_code_depnum_ccdc_archive 'CCDC 955721'