# 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_H.2PIC _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C46 H30 O2, 2(C6 H7 N)' _chemical_formula_sum 'C58 H44 N2 O2' _chemical_formula_weight 800.95 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' N N 0.0061 0.0033 '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' 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 39.4230(14) _cell_length_b 11.9620(4) _cell_length_c 18.9960(4) _cell_angle_alpha 90.00 _cell_angle_beta 106.610(2) _cell_angle_gamma 90.00 _cell_volume 8584.3(5) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 19947 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.45 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3376 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9766 _exptl_absorpt_correction_T_max 0.9911 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.0\% \f scans and \w scans' _diffrn_reflns_number 19074 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -51 _diffrn_reflns_limit_h_max 51 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 27.45 _reflns_number_total 9769 _reflns_number_gt 7509 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT program (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0444P)^2^+4.2991P] 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_number_reflns 9769 _refine_ls_number_parameters 569 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0577 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1008 _refine_ls_wR_factor_gt 0.0919 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; CELL 0.71073 39.4230 11.9620 18.9960 90.000 106.610 90.000 ZERR 8.0000 0.0014 0.0004 0.0004 0.000 0.002 0.000 LATT 7 SYMM -X, Y, 0.5-Z SFAC C N O H UNIT 464 16 16 352 MERG 2 FMAP 2 GRID PLAN 1 TEMP -100 SIZE 0.121 0.15 0.32 BOND $H CONF HTAB O34 O13 HTAB O13 N1G OMIT -2 0 2 OMIT 4 0 0 OMIT 1 1 0 OMIT 0 0 2 OMIT 2 0 0 OMIT -1 1 1 OMIT 1 1 1 OMIT 6 0 2 L.S. 20 ACTA WGHT 0.044400 4.299100 FVAR 0.20674 O13 3 0.163689 0.508164 0.079233 11.00000 0.02690 0.02293 = 0.02868 0.00493 0.01069 0.00255 H13 4 0.179179 0.525830 0.051048 11.00000 0.05886 O34 3 0.152549 0.616413 0.194409 11.00000 0.02304 0.02696 = 0.02845 -0.00108 0.00261 0.00373 H34 4 0.161330 0.589683 0.156591 11.00000 0.06502 N1G 2 0.208072 0.559993 -0.001454 11.00000 0.03815 0.03734 = 0.03022 0.00729 0.01215 0.00106 N8G 2 0.039599 1.028637 0.416901 11.00000 0.03916 0.03862 = 0.04784 -0.00355 0.01378 -0.00780 C1 1 0.214343 0.407522 0.157543 11.00000 0.02214 0.03194 = 0.02219 0.00546 0.00736 -0.00163 C2 1 0.231123 0.483474 0.211470 11.00000 0.03047 0.04094 = 0.02450 0.00123 0.00719 -0.00468 AFIX 43 H2 4 0.218158 0.541655 0.226006 11.00000 -1.20000 AFIX 0 C3 1 0.267403 0.472421 0.243778 11.00000 0.03062 0.06011 = 0.02858 -0.00027 0.00319 -0.01157 AFIX 43 H3 4 0.279429 0.524260 0.280297 11.00000 -1.20000 AFIX 0 C4 1 0.286148 0.386464 0.223157 11.00000 0.02179 0.07293 = 0.03914 0.00986 0.00173 -0.00181 AFIX 43 H4 4 0.310766 0.378904 0.246786 11.00000 -1.20000 AFIX 0 C5 1 0.269515 0.311302 0.168544 11.00000 0.02632 0.05303 = 0.04207 0.00925 0.01230 0.00781 AFIX 43 H5 4 0.282511 0.252748 0.154493 11.00000 -1.20000 AFIX 0 C6 1 0.233407 0.323446 0.134776 11.00000 0.02444 0.03470 = 0.02898 0.00690 0.01097 0.00228 C7 1 0.209331 0.263489 0.072438 11.00000 0.02874 0.02688 = 0.03008 0.00519 0.01382 0.00215 C8 1 0.215825 0.178989 0.027920 11.00000 0.03789 0.02795 = 0.04531 0.00187 0.02157 0.00469 AFIX 43 H8 4 0.238636 0.146066 0.037816 11.00000 -1.20000 AFIX 0 C9 1 0.188309 0.143600 -0.031338 11.00000 0.05422 0.02774 = 0.04205 -0.00587 0.02592 -0.00206 AFIX 43 H9 4 0.192413 0.086067 -0.062398 11.00000 -1.20000 AFIX 0 C10 1 0.154937 0.190907 -0.045896 11.00000 0.04590 0.03330 = 0.02983 -0.00434 0.01026 -0.00635 AFIX 43 H10 4 0.136510 0.165894 -0.086995 11.00000 -1.20000 AFIX 0 C11 1 0.148110 0.274897 -0.000827 11.00000 0.03129 0.02968 = 0.02759 0.00078 0.00740 -0.00041 AFIX 43 H11 4 0.125148 0.306595 -0.010302 11.00000 -1.20000 AFIX 0 C12 1 0.175516 0.310881 0.057886 11.00000 0.02768 0.02283 = 0.02340 0.00330 0.01055 0.00044 C13 1 0.175199 0.403552 0.113598 11.00000 0.02233 0.02358 = 0.02260 0.00251 0.00684 0.00197 C14 1 0.151178 0.369738 0.161204 11.00000 0.02221 0.02069 = 0.02165 -0.00175 0.00656 -0.00146 C15 1 0.164402 0.291127 0.215030 11.00000 0.02215 0.02362 = 0.02432 -0.00093 0.00640 0.00235 AFIX 43 H15 4 0.187926 0.265304 0.222066 11.00000 -1.20000 AFIX 0 C16 1 0.144811 0.246814 0.260382 11.00000 0.02657 0.02106 = 0.02295 -0.00117 0.00612 -0.00060 C17 1 0.159002 0.168356 0.317276 11.00000 0.03059 0.03081 = 0.02853 0.00502 0.00674 0.00333 AFIX 43 H17 4 0.182678 0.143015 0.325906 11.00000 -1.20000 AFIX 0 C18 1 0.138871 0.129029 0.359700 11.00000 0.04154 0.03416 = 0.02931 0.01096 0.00858 0.00077 AFIX 43 H18 4 0.148718 0.076846 0.397756 11.00000 -1.20000 AFIX 0 C19 1 0.103646 0.165127 0.347551 11.00000 0.03948 0.03882 = 0.03543 0.00767 0.01708 -0.00518 AFIX 43 H19 4 0.089915 0.137290 0.377460 11.00000 -1.20000 AFIX 0 C20 1 0.089177 0.239899 0.293002 11.00000 0.02824 0.03309 = 0.03802 0.00474 0.01377 -0.00182 AFIX 43 H20 4 0.065372 0.263519 0.285092 11.00000 -1.20000 AFIX 0 C21 1 0.109350 0.282840 0.247873 11.00000 0.02580 0.02191 = 0.02717 -0.00114 0.00850 -0.00262 C22 1 0.095806 0.361602 0.191512 11.00000 0.02005 0.02312 = 0.03168 0.00049 0.00718 0.00022 AFIX 43 H22 4 0.071775 0.383778 0.181948 11.00000 -1.20000 AFIX 0 C23 1 0.115499 0.408202 0.149523 11.00000 0.02163 0.01894 = 0.02459 -0.00120 0.00487 -0.00127 C24 1 0.095194 0.488018 0.090599 11.00000 0.01957 0.02213 = 0.02463 0.00107 0.00741 0.00046 C25 1 0.070265 0.438207 0.033279 11.00000 0.02390 0.02101 = 0.03163 -0.00156 0.00734 -0.00073 AFIX 43 H25 4 0.068324 0.359039 0.033024 11.00000 -1.20000 AFIX 0 C26 1 0.047350 0.498816 -0.025352 11.00000 0.02150 0.02814 = 0.02522 -0.00162 0.00663 0.00084 C27 1 0.021359 0.447033 -0.083894 11.00000 0.02554 0.03192 = 0.03371 -0.00543 0.00510 -0.00105 AFIX 43 H27 4 0.018028 0.368404 -0.083508 11.00000 -1.20000 AFIX 0 C28 1 0.001141 0.509323 -0.140668 11.00000 0.02464 0.04620 = 0.03028 -0.00681 0.00066 -0.00055 AFIX 43 H28 4 -0.016225 0.473900 -0.179442 11.00000 -1.20000 AFIX 0 C29 1 0.005898 0.625540 -0.142020 11.00000 0.02738 0.04439 = 0.02786 0.00449 0.00217 0.00632 AFIX 43 H29 4 -0.007832 0.667819 -0.182518 11.00000 -1.20000 AFIX 0 C30 1 0.030056 0.678650 -0.085747 11.00000 0.02785 0.03225 = 0.02938 0.00460 0.00634 0.00394 AFIX 43 H30 4 0.032767 0.757468 -0.087067 11.00000 -1.20000 AFIX 0 C31 1 0.051063 0.616353 -0.025450 11.00000 0.02118 0.02841 = 0.02509 0.00109 0.00732 0.00226 C32 1 0.075705 0.667365 0.035128 11.00000 0.02518 0.02115 = 0.02868 0.00083 0.00751 0.00070 AFIX 43 H32 4 0.077538 0.746570 0.035896 11.00000 -1.20000 AFIX 0 C33 1 0.097178 0.608112 0.093055 11.00000 0.02003 0.02229 = 0.02482 -0.00003 0.00811 -0.00007 C34 1 0.120683 0.674502 0.158451 11.00000 0.02152 0.02110 = 0.02452 0.00008 0.00496 0.00099 C35 1 0.101422 0.701462 0.215863 11.00000 0.02157 0.02822 = 0.02331 -0.00187 0.00361 0.00000 C36 1 0.088470 0.628468 0.258133 11.00000 0.03879 0.03352 = 0.03276 -0.00257 0.01377 -0.00557 AFIX 43 H36 4 0.090853 0.550001 0.253456 11.00000 -1.20000 AFIX 0 C37 1 0.071839 0.671653 0.307788 11.00000 0.04814 0.05142 = 0.03790 -0.00425 0.02305 -0.00952 AFIX 43 H37 4 0.062642 0.622140 0.336893 11.00000 -1.20000 AFIX 0 C38 1 0.068569 0.785959 0.315175 11.00000 0.04172 0.05729 = 0.03692 -0.01208 0.01931 0.00201 AFIX 43 H38 4 0.056717 0.814035 0.348552 11.00000 -1.20000 AFIX 0 C39 1 0.082425 0.860001 0.274332 11.00000 0.03516 0.03695 = 0.03115 -0.00795 0.00509 0.00758 AFIX 43 H39 4 0.080764 0.938441 0.280441 11.00000 -1.20000 AFIX 0 C40 1 0.098777 0.817071 0.224320 11.00000 0.02300 0.02827 = 0.02438 -0.00224 0.00080 0.00320 C41 1 0.116564 0.873667 0.175702 11.00000 0.02451 0.02397 = 0.02553 -0.00137 -0.00115 -0.00003 C42 1 0.122790 0.986554 0.166875 11.00000 0.03721 0.02465 = 0.03357 -0.00289 -0.00099 0.00113 AFIX 43 H42 4 0.113945 1.041883 0.192896 11.00000 -1.20000 AFIX 0 C43 1 0.142185 1.016757 0.119290 11.00000 0.04100 0.02492 = 0.04040 0.00487 -0.00109 -0.00802 AFIX 43 H43 4 0.146855 1.093456 0.113004 11.00000 -1.20000 AFIX 0 C44 1 0.154779 0.936031 0.080914 11.00000 0.03321 0.03661 = 0.03755 0.00816 0.00622 -0.00879 AFIX 43 H44 4 0.167982 0.958190 0.048537 11.00000 -1.20000 AFIX 0 C45 1 0.148406 0.822695 0.088994 11.00000 0.02911 0.03036 = 0.03278 0.00102 0.00817 -0.00233 AFIX 43 H45 4 0.156950 0.767630 0.062283 11.00000 -1.20000 AFIX 0 C46 1 0.129297 0.792452 0.136963 11.00000 0.02148 0.02351 = 0.02590 -0.00078 0.00175 -0.00200 C2G 1 0.196997 0.558222 -0.075246 11.00000 0.04152 0.03771 = 0.03317 0.00991 0.00884 0.00391 C3G 1 0.219710 0.587593 -0.116250 11.00000 0.05167 0.05169 = 0.02832 0.00794 0.01529 0.01157 AFIX 43 H3G 4 0.211607 0.585683 -0.168384 11.00000 -1.20000 AFIX 0 C4G 1 0.253827 0.619347 -0.081481 11.00000 0.04326 0.05350 = 0.04467 0.01300 0.02535 0.01325 AFIX 43 H4G 4 0.269427 0.640214 -0.109186 11.00000 -1.20000 AFIX 0 C5G 1 0.265153 0.620559 -0.005853 11.00000 0.03431 0.04373 = 0.04459 0.00470 0.01397 0.00363 AFIX 43 H5G 4 0.288650 0.642036 0.019682 11.00000 -1.20000 AFIX 0 C6G 1 0.241554 0.589870 0.031661 11.00000 0.03990 0.03900 = 0.03035 0.00252 0.01047 0.00077 AFIX 43 H6G 4 0.249411 0.589856 0.083829 11.00000 -1.20000 AFIX 0 C7G 1 0.159519 0.523866 -0.110838 11.00000 0.05157 0.07700 = 0.04536 0.02129 -0.00146 -0.01396 AFIX 137 H7A 4 0.154887 0.452140 -0.090422 11.00000 -1.50000 H7C 4 0.155666 0.516177 -0.163911 11.00000 -1.50000 H7B 4 0.143451 0.580777 -0.101498 11.00000 -1.50000 AFIX 0 C9G 1 0.006525 0.989257 0.394045 11.00000 0.04097 0.04044 = 0.04578 -0.01422 0.01402 -0.00695 C10G 1 -0.004181 0.896772 0.426291 11.00000 0.04509 0.04215 = 0.07321 -0.01885 0.03149 -0.01354 AFIX 43 H10G 4 -0.027763 0.869866 0.408495 11.00000 -1.20000 AFIX 0 C11G 1 0.019502 0.844462 0.484015 11.00000 0.06953 0.03269 = 0.06867 -0.00523 0.04450 -0.00651 AFIX 43 H11G 4 0.012519 0.781383 0.506898 11.00000 -1.20000 AFIX 0 C12G 1 0.053542 0.884839 0.508245 11.00000 0.06067 0.03517 = 0.05448 -0.00031 0.02285 0.00371 AFIX 43 H12G 4 0.070551 0.850610 0.548206 11.00000 -1.20000 AFIX 0 C13G 1 0.062253 0.976205 0.472955 11.00000 0.03995 0.03750 = 0.05512 -0.00094 0.01272 -0.00326 AFIX 43 H13G 4 0.085819 1.003621 0.489493 11.00000 -1.20000 AFIX 0 C14G 1 -0.018701 1.052208 0.332641 11.00000 0.05625 0.07187 = 0.06095 -0.00798 -0.00362 -0.00857 AFIX 137 H14A 4 -0.022466 1.010310 0.286712 11.00000 -1.50000 H14B 4 -0.008756 1.125805 0.327472 11.00000 -1.50000 H14C 4 -0.041350 1.061605 0.343653 11.00000 -1.50000 HKLF 4 END ; 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 O13 O 0.16369(2) 0.50816(7) 0.07923(4) 0.02560(18) Uani 1 1 d . . . H13 H 0.1792(4) 0.5258(14) 0.0510(9) 0.059(5) Uiso 1 1 d . . . O34 O 0.15255(2) 0.61641(7) 0.19441(5) 0.02713(19) Uani 1 1 d . . . H34 H 0.1613(5) 0.5897(16) 0.1566(10) 0.065(5) Uiso 1 1 d . . . N1G N 0.20807(3) 0.55999(9) -0.00145(6) 0.0347(3) Uani 1 1 d . . . N8G N 0.03960(3) 1.02864(10) 0.41690(7) 0.0416(3) Uani 1 1 d . . . C1 C 0.21434(3) 0.40752(10) 0.15754(6) 0.0252(2) Uani 1 1 d . . . C2 C 0.23112(3) 0.48347(12) 0.21147(7) 0.0321(3) Uani 1 1 d . . . H2 H 0.2182 0.5417 0.2260 0.039 Uiso 1 1 calc R . . C3 C 0.26740(4) 0.47242(14) 0.24378(7) 0.0409(3) Uani 1 1 d . . . H3 H 0.2794 0.5243 0.2803 0.049 Uiso 1 1 calc R . . C4 C 0.28615(3) 0.38646(15) 0.22316(8) 0.0461(4) Uani 1 1 d . . . H4 H 0.3108 0.3789 0.2468 0.055 Uiso 1 1 calc R . . C5 C 0.26951(3) 0.31130(13) 0.16854(8) 0.0400(3) Uani 1 1 d . . . H5 H 0.2825 0.2527 0.1545 0.048 Uiso 1 1 calc R . . C6 C 0.23341(3) 0.32345(11) 0.13478(7) 0.0287(3) Uani 1 1 d . . . C7 C 0.20933(3) 0.26349(10) 0.07244(7) 0.0274(3) Uani 1 1 d . . . C8 C 0.21582(4) 0.17899(11) 0.02792(8) 0.0350(3) Uani 1 1 d . . . H8 H 0.2386 0.1461 0.0378 0.042 Uiso 1 1 calc R . . C9 C 0.18831(4) 0.14360(11) -0.03134(8) 0.0388(3) Uani 1 1 d . . . H9 H 0.1924 0.0861 -0.0624 0.047 Uiso 1 1 calc R . . C10 C 0.15494(4) 0.19091(11) -0.04590(7) 0.0365(3) Uani 1 1 d . . . H10 H 0.1365 0.1659 -0.0870 0.044 Uiso 1 1 calc R . . C11 C 0.14811(3) 0.27490(10) -0.00083(7) 0.0297(3) Uani 1 1 d . . . H11 H 0.1251 0.3066 -0.0103 0.036 Uiso 1 1 calc R . . C12 C 0.17552(3) 0.31088(10) 0.05789(6) 0.0240(2) Uani 1 1 d . . . C13 C 0.17520(3) 0.40355(10) 0.11360(6) 0.0228(2) Uani 1 1 d . . . C14 C 0.15118(3) 0.36974(9) 0.16120(6) 0.0215(2) Uani 1 1 d . . . C15 C 0.16440(3) 0.29113(10) 0.21503(6) 0.0234(2) Uani 1 1 d . . . H15 H 0.1879 0.2653 0.2221 0.028 Uiso 1 1 calc R . . C16 C 0.14481(3) 0.24681(9) 0.26038(6) 0.0237(2) Uani 1 1 d . . . C17 C 0.15900(3) 0.16836(11) 0.31728(7) 0.0303(3) Uani 1 1 d . . . H17 H 0.1827 0.1430 0.3259 0.036 Uiso 1 1 calc R . . C18 C 0.13887(4) 0.12903(11) 0.35970(7) 0.0353(3) Uani 1 1 d . . . H18 H 0.1487 0.0768 0.3978 0.042 Uiso 1 1 calc R . . C19 C 0.10365(4) 0.16513(12) 0.34755(7) 0.0366(3) Uani 1 1 d . . . H19 H 0.0899 0.1373 0.3775 0.044 Uiso 1 1 calc R . . C20 C 0.08918(3) 0.23990(11) 0.29300(7) 0.0322(3) Uani 1 1 d . . . H20 H 0.0654 0.2635 0.2851 0.039 Uiso 1 1 calc R . . C21 C 0.10935(3) 0.28284(10) 0.24787(6) 0.0248(2) Uani 1 1 d . . . C22 C 0.09581(3) 0.36160(10) 0.19151(6) 0.0250(2) Uani 1 1 d . . . H22 H 0.0718 0.3838 0.1819 0.030 Uiso 1 1 calc R . . C23 C 0.11550(3) 0.40820(9) 0.14952(6) 0.0221(2) Uani 1 1 d . . . C24 C 0.09519(3) 0.48802(9) 0.09060(6) 0.0219(2) Uani 1 1 d . . . C25 C 0.07026(3) 0.43821(10) 0.03328(6) 0.0256(2) Uani 1 1 d . . . H25 H 0.0683 0.3590 0.0330 0.031 Uiso 1 1 calc R . . C26 C 0.04735(3) 0.49882(10) -0.02535(6) 0.0250(2) Uani 1 1 d . . . C27 C 0.02136(3) 0.44703(11) -0.08389(7) 0.0311(3) Uani 1 1 d . . . H27 H 0.0180 0.3684 -0.0835 0.037 Uiso 1 1 calc R . . C28 C 0.00114(3) 0.50932(12) -0.14067(7) 0.0352(3) Uani 1 1 d . . . H28 H -0.0162 0.4739 -0.1794 0.042 Uiso 1 1 calc R . . C29 C 0.00590(3) 0.62554(12) -0.14202(7) 0.0344(3) Uani 1 1 d . . . H29 H -0.0078 0.6678 -0.1825 0.041 Uiso 1 1 calc R . . C30 C 0.03006(3) 0.67865(11) -0.08575(7) 0.0302(3) Uani 1 1 d . . . H30 H 0.0328 0.7575 -0.0871 0.036 Uiso 1 1 calc R . . C31 C 0.05106(3) 0.61635(10) -0.02545(6) 0.0247(2) Uani 1 1 d . . . C32 C 0.07570(3) 0.66736(10) 0.03513(6) 0.0250(2) Uani 1 1 d . . . H32 H 0.0775 0.7466 0.0359 0.030 Uiso 1 1 calc R . . C33 C 0.09718(3) 0.60811(9) 0.09306(6) 0.0220(2) Uani 1 1 d . . . C34 C 0.12068(3) 0.67450(9) 0.15845(6) 0.0227(2) Uani 1 1 d . . . C35 C 0.10142(3) 0.70146(10) 0.21586(6) 0.0249(2) Uani 1 1 d . . . C36 C 0.08847(3) 0.62847(12) 0.25813(7) 0.0343(3) Uani 1 1 d . . . H36 H 0.0909 0.5500 0.2535 0.041 Uiso 1 1 calc R . . C37 C 0.07184(4) 0.67165(13) 0.30779(8) 0.0436(3) Uani 1 1 d . . . H37 H 0.0626 0.6221 0.3369 0.052 Uiso 1 1 calc R . . C38 C 0.06857(4) 0.78596(14) 0.31517(8) 0.0436(4) Uani 1 1 d . . . H38 H 0.0567 0.8140 0.3486 0.052 Uiso 1 1 calc R . . C39 C 0.08242(3) 0.86000(12) 0.27433(7) 0.0353(3) Uani 1 1 d . . . H39 H 0.0808 0.9384 0.2804 0.042 Uiso 1 1 calc R . . C40 C 0.09878(3) 0.81707(10) 0.22432(6) 0.0265(3) Uani 1 1 d . . . C41 C 0.11656(3) 0.87367(10) 0.17570(6) 0.0264(3) Uani 1 1 d . . . C42 C 0.12279(3) 0.98655(11) 0.16688(7) 0.0341(3) Uani 1 1 d . . . H42 H 0.1139 1.0419 0.1929 0.041 Uiso 1 1 calc R . . C43 C 0.14218(4) 1.01676(11) 0.11929(7) 0.0381(3) Uani 1 1 d . . . H43 H 0.1469 1.0935 0.1130 0.046 Uiso 1 1 calc R . . C44 C 0.15478(3) 0.93603(11) 0.08091(8) 0.0366(3) Uani 1 1 d . . . H44 H 0.1680 0.9582 0.0485 0.044 Uiso 1 1 calc R . . C45 C 0.14841(3) 0.82270(11) 0.08899(7) 0.0309(3) Uani 1 1 d . . . H45 H 0.1569 0.7676 0.0623 0.037 Uiso 1 1 calc R . . C46 C 0.12930(3) 0.79245(10) 0.13696(6) 0.0247(2) Uani 1 1 d . . . C2G C 0.19700(4) 0.55822(12) -0.07525(7) 0.0379(3) Uani 1 1 d . . . C3G C 0.21971(4) 0.58759(13) -0.11625(8) 0.0431(3) Uani 1 1 d . . . H3G H 0.2116 0.5857 -0.1684 0.052 Uiso 1 1 calc R . . C4G C 0.25383(4) 0.61935(13) -0.08148(8) 0.0445(4) Uani 1 1 d . . . H4G H 0.2694 0.6402 -0.1092 0.053 Uiso 1 1 calc R . . C5G C 0.26515(4) 0.62056(12) -0.00585(8) 0.0403(3) Uani 1 1 d . . . H5G H 0.2887 0.6420 0.0197 0.048 Uiso 1 1 calc R . . C6G C 0.24155(4) 0.58987(12) 0.03166(7) 0.0363(3) Uani 1 1 d . . . H6G H 0.2494 0.5899 0.0838 0.044 Uiso 1 1 calc R . . C7G C 0.15952(4) 0.52387(17) -0.11084(9) 0.0612(5) Uani 1 1 d . . . H7A H 0.1549 0.4521 -0.0904 0.092 Uiso 1 1 calc R . . H7C H 0.1557 0.5162 -0.1639 0.092 Uiso 1 1 calc R . . H7B H 0.1435 0.5808 -0.1015 0.092 Uiso 1 1 calc R . . C9G C 0.00653(4) 0.98926(13) 0.39405(8) 0.0421(3) Uani 1 1 d . . . C10G C -0.00418(4) 0.89677(13) 0.42629(10) 0.0505(4) Uani 1 1 d . . . H10G H -0.0278 0.8699 0.4085 0.061 Uiso 1 1 calc R . . C11G C 0.01950(5) 0.84446(13) 0.48401(10) 0.0518(4) Uani 1 1 d . . . H11G H 0.0125 0.7814 0.5069 0.062 Uiso 1 1 calc R . . C12G C 0.05354(5) 0.88484(13) 0.50824(9) 0.0488(4) Uani 1 1 d . . . H12G H 0.0706 0.8506 0.5482 0.059 Uiso 1 1 calc R . . C13G C 0.06225(4) 0.97621(12) 0.47296(9) 0.0444(3) Uani 1 1 d . . . H13G H 0.0858 1.0036 0.4895 0.053 Uiso 1 1 calc R . . C14G C -0.01870(5) 1.05221(17) 0.33264(10) 0.0673(5) Uani 1 1 d . . . H14A H -0.0225 1.0103 0.2867 0.101 Uiso 1 1 calc R . . H14B H -0.0088 1.1258 0.3275 0.101 Uiso 1 1 calc R . . H14C H -0.0413 1.0616 0.3437 0.101 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 O13 0.0269(4) 0.0229(4) 0.0287(4) 0.0049(3) 0.0107(4) 0.0026(3) O34 0.0230(4) 0.0270(4) 0.0284(4) -0.0011(4) 0.0026(3) 0.0037(3) N1G 0.0381(6) 0.0373(6) 0.0302(6) 0.0073(5) 0.0121(5) 0.0011(5) N8G 0.0392(6) 0.0386(7) 0.0478(7) -0.0035(6) 0.0138(6) -0.0078(5) C1 0.0221(5) 0.0319(6) 0.0222(6) 0.0055(5) 0.0074(5) -0.0016(5) C2 0.0305(6) 0.0409(7) 0.0245(6) 0.0012(5) 0.0072(5) -0.0047(5) C3 0.0306(7) 0.0601(10) 0.0286(7) -0.0003(6) 0.0032(6) -0.0116(6) C4 0.0218(6) 0.0729(11) 0.0391(8) 0.0099(8) 0.0017(6) -0.0018(7) C5 0.0263(6) 0.0530(9) 0.0421(8) 0.0092(7) 0.0123(6) 0.0078(6) C6 0.0244(6) 0.0347(7) 0.0290(6) 0.0069(5) 0.0110(5) 0.0023(5) C7 0.0287(6) 0.0269(6) 0.0301(6) 0.0052(5) 0.0138(5) 0.0022(5) C8 0.0379(7) 0.0280(7) 0.0453(8) 0.0019(6) 0.0216(6) 0.0047(5) C9 0.0542(9) 0.0277(7) 0.0420(8) -0.0059(6) 0.0259(7) -0.0021(6) C10 0.0459(8) 0.0333(7) 0.0298(7) -0.0043(6) 0.0103(6) -0.0063(6) C11 0.0313(6) 0.0297(7) 0.0276(6) 0.0008(5) 0.0074(5) -0.0004(5) C12 0.0277(6) 0.0228(6) 0.0234(6) 0.0033(5) 0.0106(5) 0.0004(5) C13 0.0223(5) 0.0236(6) 0.0226(6) 0.0025(5) 0.0068(5) 0.0020(4) C14 0.0222(5) 0.0207(5) 0.0217(5) -0.0018(4) 0.0066(4) -0.0015(4) C15 0.0222(5) 0.0236(6) 0.0243(6) -0.0009(5) 0.0064(5) 0.0024(4) C16 0.0266(6) 0.0211(6) 0.0229(6) -0.0012(5) 0.0061(5) -0.0006(5) C17 0.0306(6) 0.0308(7) 0.0285(6) 0.0050(5) 0.0067(5) 0.0033(5) C18 0.0415(7) 0.0342(7) 0.0293(7) 0.0110(6) 0.0086(6) 0.0008(6) C19 0.0395(7) 0.0388(8) 0.0354(7) 0.0077(6) 0.0171(6) -0.0052(6) C20 0.0282(6) 0.0331(7) 0.0380(7) 0.0047(6) 0.0138(6) -0.0018(5) C21 0.0258(6) 0.0219(6) 0.0272(6) -0.0011(5) 0.0085(5) -0.0026(5) C22 0.0200(5) 0.0231(6) 0.0317(6) 0.0005(5) 0.0072(5) 0.0002(4) C23 0.0216(5) 0.0189(5) 0.0246(6) -0.0012(4) 0.0049(4) -0.0013(4) C24 0.0196(5) 0.0221(6) 0.0246(6) 0.0011(5) 0.0074(4) 0.0005(4) C25 0.0239(6) 0.0210(6) 0.0316(6) -0.0016(5) 0.0073(5) -0.0007(5) C26 0.0215(5) 0.0281(6) 0.0252(6) -0.0016(5) 0.0066(5) 0.0008(5) C27 0.0255(6) 0.0319(7) 0.0337(7) -0.0054(5) 0.0051(5) -0.0010(5) C28 0.0246(6) 0.0462(8) 0.0303(7) -0.0068(6) 0.0007(5) -0.0006(6) C29 0.0274(6) 0.0444(8) 0.0279(6) 0.0045(6) 0.0022(5) 0.0063(6) C30 0.0278(6) 0.0323(7) 0.0294(6) 0.0046(5) 0.0063(5) 0.0039(5) C31 0.0212(5) 0.0284(6) 0.0251(6) 0.0011(5) 0.0073(5) 0.0023(5) C32 0.0252(6) 0.0211(6) 0.0287(6) 0.0008(5) 0.0075(5) 0.0007(4) C33 0.0200(5) 0.0223(6) 0.0248(6) 0.0000(5) 0.0081(4) -0.0001(4) C34 0.0215(5) 0.0211(6) 0.0245(6) 0.0001(5) 0.0050(5) 0.0010(4) C35 0.0216(5) 0.0282(6) 0.0233(6) -0.0019(5) 0.0036(5) 0.0000(5) C36 0.0388(7) 0.0335(7) 0.0328(7) -0.0026(6) 0.0138(6) -0.0056(6) C37 0.0481(8) 0.0514(9) 0.0379(8) -0.0042(7) 0.0231(7) -0.0095(7) C38 0.0417(8) 0.0573(10) 0.0369(8) -0.0121(7) 0.0193(6) 0.0020(7) C39 0.0352(7) 0.0370(7) 0.0312(7) -0.0079(6) 0.0051(6) 0.0076(6) C40 0.0230(6) 0.0283(6) 0.0244(6) -0.0022(5) 0.0008(5) 0.0032(5) C41 0.0245(6) 0.0240(6) 0.0255(6) -0.0014(5) -0.0012(5) 0.0000(5) C42 0.0372(7) 0.0246(6) 0.0336(7) -0.0029(5) -0.0010(6) 0.0011(5) C43 0.0410(8) 0.0249(7) 0.0404(8) 0.0049(6) -0.0011(6) -0.0080(6) C44 0.0332(7) 0.0366(7) 0.0376(7) 0.0082(6) 0.0062(6) -0.0088(6) C45 0.0291(6) 0.0304(7) 0.0328(7) 0.0010(5) 0.0082(5) -0.0023(5) C46 0.0215(5) 0.0235(6) 0.0259(6) -0.0008(5) 0.0017(5) -0.0020(4) C2G 0.0415(8) 0.0377(8) 0.0332(7) 0.0099(6) 0.0088(6) 0.0039(6) C3G 0.0517(9) 0.0517(9) 0.0283(7) 0.0079(6) 0.0153(6) 0.0116(7) C4G 0.0433(8) 0.0535(9) 0.0447(8) 0.0130(7) 0.0253(7) 0.0132(7) C5G 0.0343(7) 0.0437(8) 0.0446(8) 0.0047(7) 0.0140(6) 0.0036(6) C6G 0.0399(7) 0.0390(8) 0.0303(7) 0.0025(6) 0.0105(6) 0.0008(6) C7G 0.0516(10) 0.0770(13) 0.0454(9) 0.0213(9) -0.0015(8) -0.0140(9) C9G 0.0410(8) 0.0404(8) 0.0458(8) -0.0142(7) 0.0140(7) -0.0069(6) C10G 0.0451(9) 0.0422(9) 0.0732(11) -0.0189(8) 0.0315(8) -0.0135(7) C11G 0.0695(11) 0.0327(8) 0.0687(11) -0.0052(8) 0.0445(10) -0.0065(8) C12G 0.0607(10) 0.0352(8) 0.0545(9) -0.0003(7) 0.0229(8) 0.0037(7) C13G 0.0400(8) 0.0375(8) 0.0551(9) -0.0009(7) 0.0127(7) -0.0033(6) C14G 0.0562(11) 0.0719(13) 0.0610(11) -0.0080(10) -0.0036(9) -0.0086(9) _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 O13 C13 1.4243(14) . ? O13 H13 0.944(18) . ? O34 C34 1.4272(13) . ? O34 H34 0.938(19) . ? N1G C6G 1.3383(17) . ? N1G C2G 1.3439(17) . ? N8G C13G 1.3346(19) . ? N8G C9G 1.3367(18) . ? C1 C2 1.3874(17) . ? C1 C6 1.3961(17) . ? C1 C13 1.5310(15) . ? C2 C3 1.3921(18) . ? C2 H2 0.9500 . ? C3 C4 1.386(2) . ? C3 H3 0.9500 . ? C4 C5 1.388(2) . ? C4 H4 0.9500 . ? C5 C6 1.3917(17) . ? C5 H5 0.9500 . ? C6 C7 1.4748(18) . ? C7 C8 1.3879(18) . ? C7 C12 1.4015(16) . ? C8 C9 1.387(2) . ? C8 H8 0.9500 . ? C9 C10 1.386(2) . ? C9 H9 0.9500 . ? C10 C11 1.3952(18) . ? C10 H10 0.9500 . ? C11 C12 1.3812(17) . ? C11 H11 0.9500 . ? C12 C13 1.5351(16) . ? C13 C14 1.5388(15) . ? C14 C15 1.3772(16) . ? C14 C23 1.4356(15) . ? C15 C16 1.4142(16) . ? C15 H15 0.9500 . ? C16 C21 1.4165(16) . ? C16 C17 1.4199(16) . ? C17 C18 1.3661(17) . ? C17 H17 0.9500 . ? C18 C19 1.4089(19) . ? C18 H18 0.9500 . ? C19 C20 1.3642(18) . ? C19 H19 0.9500 . ? C20 C21 1.4216(16) . ? C20 H20 0.9500 . ? C21 C22 1.4114(16) . ? C22 C23 1.3797(16) . ? C22 H22 0.9500 . ? C23 C24 1.5143(15) . ? C24 C25 1.3765(16) . ? C24 C33 1.4387(16) . ? C25 C26 1.4167(16) . ? C25 H25 0.9500 . ? C26 C31 1.4136(17) . ? C26 C27 1.4209(16) . ? C27 C28 1.3646(18) . ? C27 H27 0.9500 . ? C28 C29 1.404(2) . ? C28 H28 0.9500 . ? C29 C30 1.3680(18) . ? C29 H29 0.9500 . ? C30 C31 1.4180(16) . ? C30 H30 0.9500 . ? C31 C32 1.4146(16) . ? C32 C33 1.3774(16) . ? C32 H32 0.9500 . ? C33 C34 1.5409(16) . ? C34 C35 1.5308(16) . ? C34 C46 1.5336(16) . ? C35 C36 1.3793(17) . ? C35 C40 1.3995(17) . ? C36 C37 1.3928(18) . ? C36 H36 0.9500 . ? C37 C38 1.384(2) . ? C37 H37 0.9500 . ? C38 C39 1.388(2) . ? C38 H38 0.9500 . ? C39 C40 1.3900(17) . ? C39 H39 0.9500 . ? C40 C41 1.4742(17) . ? C41 C42 1.3912(17) . ? C41 C46 1.3959(17) . ? C42 C43 1.388(2) . ? C42 H42 0.9500 . ? C43 C44 1.385(2) . ? C43 H43 0.9500 . ? C44 C45 1.3952(18) . ? C44 H44 0.9500 . ? C45 C46 1.3860(17) . ? C45 H45 0.9500 . ? C2G C3G 1.3894(19) . ? C2G C7G 1.496(2) . ? C3G C4G 1.372(2) . ? C3G H3G 0.9500 . ? C4G C5G 1.377(2) . ? C4G H4G 0.9500 . ? C5G C6G 1.3737(19) . ? C5G H5G 0.9500 . ? C6G H6G 0.9500 . ? C7G H7A 0.9800 . ? C7G H7C 0.9800 . ? C7G H7B 0.9800 . ? C9G C10G 1.387(2) . ? C9G C14G 1.501(2) . ? C10G C11G 1.371(2) . ? C10G H10G 0.9500 . ? C11G C12G 1.376(2) . ? C11G H11G 0.9500 . ? C12G C13G 1.376(2) . ? C12G H12G 0.9500 . ? C13G H13G 0.9500 . ? C14G H14A 0.9800 . ? C14G H14B 0.9800 . ? C14G H14C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O13 H13 106.5(10) . . ? C34 O34 H34 105.5(11) . . ? C6G N1G C2G 118.50(11) . . ? C13G N8G C9G 117.50(13) . . ? C2 C1 C6 121.01(11) . . ? C2 C1 C13 128.05(11) . . ? C6 C1 C13 110.90(10) . . ? C1 C2 C3 118.44(13) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C4 C3 C2 120.62(13) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 121.04(12) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C4 C5 C6 118.65(13) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C5 C6 C1 120.18(12) . . ? C5 C6 C7 131.15(12) . . ? C1 C6 C7 108.61(10) . . ? C8 C7 C12 120.34(12) . . ? C8 C7 C6 130.92(11) . . ? C12 C7 C6 108.62(10) . . ? C9 C8 C7 118.62(12) . . ? C9 C8 H8 120.7 . . ? C7 C8 H8 120.7 . . ? C10 C9 C8 120.99(12) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 120.69(13) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C12 C11 C10 118.45(12) . . ? C12 C11 H11 120.8 . . ? C10 C11 H11 120.8 . . ? C11 C12 C7 120.90(11) . . ? C11 C12 C13 128.54(10) . . ? C7 C12 C13 110.54(10) . . ? O13 C13 C1 111.23(9) . . ? O13 C13 C12 112.51(9) . . ? C1 C13 C12 101.11(9) . . ? O13 C13 C14 109.35(9) . . ? C1 C13 C14 112.42(9) . . ? C12 C13 C14 110.06(9) . . ? C15 C14 C23 118.67(10) . . ? C15 C14 C13 116.73(10) . . ? C23 C14 C13 124.42(10) . . ? C14 C15 C16 123.47(10) . . ? C14 C15 H15 118.3 . . ? C16 C15 H15 118.3 . . ? C15 C16 C21 117.93(10) . . ? C15 C16 C17 123.12(11) . . ? C21 C16 C17 118.95(10) . . ? C18 C17 C16 120.51(12) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 120.63(12) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C20 C19 C18 120.26(12) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 120.69(12) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C22 C21 C16 118.13(10) . . ? C22 C21 C20 122.89(11) . . ? C16 C21 C20 118.97(11) . . ? C23 C22 C21 123.70(10) . . ? C23 C22 H22 118.2 . . ? C21 C22 H22 118.2 . . ? C22 C23 C14 118.00(10) . . ? C22 C23 C24 114.59(10) . . ? C14 C23 C24 127.15(10) . . ? C25 C24 C33 118.54(10) . . ? C25 C24 C23 114.76(10) . . ? C33 C24 C23 126.39(10) . . ? C24 C25 C26 123.44(11) . . ? C24 C25 H25 118.3 . . ? C26 C25 H25 118.3 . . ? C31 C26 C25 117.84(10) . . ? C31 C26 C27 118.97(11) . . ? C25 C26 C27 123.18(11) . . ? C28 C27 C26 120.54(12) . . ? C28 C27 H27 119.7 . . ? C26 C27 H27 119.7 . . ? C27 C28 C29 120.28(12) . . ? C27 C28 H28 119.9 . . ? C29 C28 H28 119.9 . . ? C30 C29 C28 120.82(12) . . ? C30 C29 H29 119.6 . . ? C28 C29 H29 119.6 . . ? C29 C30 C31 120.17(12) . . ? C29 C30 H30 119.9 . . ? C31 C30 H30 119.9 . . ? C26 C31 C32 118.37(10) . . ? C26 C31 C30 119.14(11) . . ? C32 C31 C30 122.49(11) . . ? C33 C32 C31 123.38(11) . . ? C33 C32 H32 118.3 . . ? C31 C32 H32 118.3 . . ? C32 C33 C24 118.20(10) . . ? C32 C33 C34 118.00(10) . . ? C24 C33 C34 123.73(10) . . ? O34 C34 C35 108.04(9) . . ? O34 C34 C46 110.10(9) . . ? C35 C34 C46 100.86(9) . . ? O34 C34 C33 112.28(9) . . ? C35 C34 C33 112.11(9) . . ? C46 C34 C33 112.80(9) . . ? C36 C35 C40 120.44(11) . . ? C36 C35 C34 128.53(11) . . ? C40 C35 C34 111.00(10) . . ? C35 C36 C37 118.93(13) . . ? C35 C36 H36 120.5 . . ? C37 C36 H36 120.5 . . ? C38 C37 C36 120.70(13) . . ? C38 C37 H37 119.7 . . ? C36 C37 H37 119.7 . . ? C37 C38 C39 120.71(12) . . ? C37 C38 H38 119.6 . . ? C39 C38 H38 119.6 . . ? C38 C39 C40 118.67(13) . . ? C38 C39 H39 120.7 . . ? C40 C39 H39 120.7 . . ? C39 C40 C35 120.52(12) . . ? C39 C40 C41 130.93(12) . . ? C35 C40 C41 108.51(10) . . ? C42 C41 C46 120.63(12) . . ? C42 C41 C40 130.78(12) . . ? C46 C41 C40 108.53(10) . . ? C43 C42 C41 118.69(12) . . ? C43 C42 H42 120.7 . . ? C41 C42 H42 120.7 . . ? C44 C43 C42 120.56(12) . . ? C44 C43 H43 119.7 . . ? C42 C43 H43 119.7 . . ? C43 C44 C45 121.12(12) . . ? C43 C44 H44 119.4 . . ? C45 C44 H44 119.4 . . ? C46 C45 C44 118.34(12) . . ? C46 C45 H45 120.8 . . ? C44 C45 H45 120.8 . . ? C45 C46 C41 120.66(11) . . ? C45 C46 C34 128.20(11) . . ? C41 C46 C34 111.08(10) . . ? N1G C2G C3G 120.76(13) . . ? N1G C2G C7G 117.40(13) . . ? C3G C2G C7G 121.84(13) . . ? C4G C3G C2G 120.03(13) . . ? C4G C3G H3G 120.0 . . ? C2G C3G H3G 120.0 . . ? C3G C4G C5G 119.08(13) . . ? C3G C4G H4G 120.5 . . ? C5G C4G H4G 120.5 . . ? C6G C5G C4G 118.20(14) . . ? C6G C5G H5G 120.9 . . ? C4G C5G H5G 120.9 . . ? N1G C6G C5G 123.42(13) . . ? N1G C6G H6G 118.3 . . ? C5G C6G H6G 118.3 . . ? C2G C7G H7A 109.5 . . ? C2G C7G H7C 109.5 . . ? H7A C7G H7C 109.5 . . ? C2G C7G H7B 109.5 . . ? H7A C7G H7B 109.5 . . ? H7C C7G H7B 109.5 . . ? N8G C9G C10G 121.95(15) . . ? N8G C9G C14G 116.34(14) . . ? C10G C9G C14G 121.70(14) . . ? C11G C10G C9G 119.56(14) . . ? C11G C10G H10G 120.2 . . ? C9G C10G H10G 120.2 . . ? C10G C11G C12G 118.91(15) . . ? C10G C11G H11G 120.5 . . ? C12G C11G H11G 120.5 . . ? C13G C12G C11G 118.11(16) . . ? C13G C12G H12G 120.9 . . ? C11G C12G H12G 120.9 . . ? N8G C13G C12G 123.97(14) . . ? N8G C13G H13G 118.0 . . ? C12G C13G H13G 118.0 . . ? C9G C14G H14A 109.5 . . ? C9G C14G H14B 109.5 . . ? H14A C14G H14B 109.5 . . ? C9G C14G H14C 109.5 . . ? H14A C14G H14C 109.5 . . ? H14B C14G H14C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.50(18) . . . . ? C13 C1 C2 C3 -178.98(11) . . . . ? C1 C2 C3 C4 -0.9(2) . . . . ? C2 C3 C4 C5 1.8(2) . . . . ? C3 C4 C5 C6 -0.3(2) . . . . ? C4 C5 C6 C1 -2.13(19) . . . . ? C4 C5 C6 C7 174.73(13) . . . . ? C2 C1 C6 C5 3.05(18) . . . . ? C13 C1 C6 C5 -179.07(11) . . . . ? C2 C1 C6 C7 -174.45(11) . . . . ? C13 C1 C6 C7 3.43(13) . . . . ? C5 C6 C7 C8 -1.8(2) . . . . ? C1 C6 C7 C8 175.32(13) . . . . ? C5 C6 C7 C12 -177.64(13) . . . . ? C1 C6 C7 C12 -0.51(13) . . . . ? C12 C7 C8 C9 0.62(18) . . . . ? C6 C7 C8 C9 -174.80(12) . . . . ? C7 C8 C9 C10 -0.3(2) . . . . ? C8 C9 C10 C11 -0.5(2) . . . . ? C9 C10 C11 C12 0.98(19) . . . . ? C10 C11 C12 C7 -0.65(18) . . . . ? C10 C11 C12 C13 177.91(11) . . . . ? C8 C7 C12 C11 -0.15(18) . . . . ? C6 C7 C12 C11 176.20(11) . . . . ? C8 C7 C12 C13 -178.95(11) . . . . ? C6 C7 C12 C13 -2.60(13) . . . . ? C2 C1 C13 O13 53.37(15) . . . . ? C6 C1 C13 O13 -124.32(10) . . . . ? C2 C1 C13 C12 173.03(11) . . . . ? C6 C1 C13 C12 -4.66(12) . . . . ? C2 C1 C13 C14 -69.64(15) . . . . ? C6 C1 C13 C14 112.67(11) . . . . ? C11 C12 C13 O13 -55.62(15) . . . . ? C7 C12 C13 O13 123.06(10) . . . . ? C11 C12 C13 C1 -174.36(11) . . . . ? C7 C12 C13 C1 4.32(12) . . . . ? C11 C12 C13 C14 66.59(15) . . . . ? C7 C12 C13 C14 -114.72(10) . . . . ? O13 C13 C14 C15 -160.53(10) . . . . ? C1 C13 C14 C15 -36.48(14) . . . . ? C12 C13 C14 C15 75.40(12) . . . . ? O13 C13 C14 C23 24.28(14) . . . . ? C1 C13 C14 C23 148.34(11) . . . . ? C12 C13 C14 C23 -99.78(12) . . . . ? C23 C14 C15 C16 -0.79(17) . . . . ? C13 C14 C15 C16 -176.27(10) . . . . ? C14 C15 C16 C21 2.14(17) . . . . ? C14 C15 C16 C17 -177.98(11) . . . . ? C15 C16 C17 C18 179.54(12) . . . . ? C21 C16 C17 C18 -0.59(18) . . . . ? C16 C17 C18 C19 0.3(2) . . . . ? C17 C18 C19 C20 0.1(2) . . . . ? C18 C19 C20 C21 -0.3(2) . . . . ? C15 C16 C21 C22 -0.67(16) . . . . ? C17 C16 C21 C22 179.45(11) . . . . ? C15 C16 C21 C20 -179.69(11) . . . . ? C17 C16 C21 C20 0.43(17) . . . . ? C19 C20 C21 C22 -178.98(12) . . . . ? C19 C20 C21 C16 -0.02(19) . . . . ? C16 C21 C22 C23 -2.20(18) . . . . ? C20 C21 C22 C23 176.78(12) . . . . ? C21 C22 C23 C14 3.54(17) . . . . ? C21 C22 C23 C24 178.14(11) . . . . ? C15 C14 C23 C22 -2.00(16) . . . . ? C13 C14 C23 C22 173.10(10) . . . . ? C15 C14 C23 C24 -175.83(11) . . . . ? C13 C14 C23 C24 -0.73(18) . . . . ? C22 C23 C24 C25 -69.85(13) . . . . ? C14 C23 C24 C25 104.16(13) . . . . ? C22 C23 C24 C33 103.60(13) . . . . ? C14 C23 C24 C33 -82.39(15) . . . . ? C33 C24 C25 C26 2.78(17) . . . . ? C23 C24 C25 C26 176.78(10) . . . . ? C24 C25 C26 C31 1.59(17) . . . . ? C24 C25 C26 C27 -179.17(11) . . . . ? C31 C26 C27 C28 2.29(18) . . . . ? C25 C26 C27 C28 -176.94(11) . . . . ? C26 C27 C28 C29 0.24(19) . . . . ? C27 C28 C29 C30 -1.9(2) . . . . ? C28 C29 C30 C31 0.86(19) . . . . ? C25 C26 C31 C32 -4.10(16) . . . . ? C27 C26 C31 C32 176.64(10) . . . . ? C25 C26 C31 C30 176.04(10) . . . . ? C27 C26 C31 C30 -3.22(17) . . . . ? C29 C30 C31 C26 1.69(17) . . . . ? C29 C30 C31 C32 -178.16(11) . . . . ? C26 C31 C32 C33 2.35(17) . . . . ? C30 C31 C32 C33 -177.80(11) . . . . ? C31 C32 C33 C24 2.03(17) . . . . ? C31 C32 C33 C34 -175.17(10) . . . . ? C25 C24 C33 C32 -4.53(16) . . . . ? C23 C24 C33 C32 -177.76(10) . . . . ? C25 C24 C33 C34 172.50(10) . . . . ? C23 C24 C33 C34 -0.73(17) . . . . ? C32 C33 C34 O34 -150.45(10) . . . . ? C24 C33 C34 O34 32.52(14) . . . . ? C32 C33 C34 C35 87.71(12) . . . . ? C24 C33 C34 C35 -89.33(13) . . . . ? C32 C33 C34 C46 -25.34(14) . . . . ? C24 C33 C34 C46 157.63(10) . . . . ? O34 C34 C35 C36 -61.23(15) . . . . ? C46 C34 C35 C36 -176.73(12) . . . . ? C33 C34 C35 C36 63.01(16) . . . . ? O34 C34 C35 C40 116.74(10) . . . . ? C46 C34 C35 C40 1.24(12) . . . . ? C33 C34 C35 C40 -119.01(11) . . . . ? C40 C35 C36 C37 1.82(19) . . . . ? C34 C35 C36 C37 179.62(12) . . . . ? C35 C36 C37 C38 -0.5(2) . . . . ? C36 C37 C38 C39 -1.3(2) . . . . ? C37 C38 C39 C40 1.8(2) . . . . ? C38 C39 C40 C35 -0.50(18) . . . . ? C38 C39 C40 C41 -177.95(12) . . . . ? C36 C35 C40 C39 -1.32(18) . . . . ? C34 C35 C40 C39 -179.48(10) . . . . ? C36 C35 C40 C41 176.65(11) . . . . ? C34 C35 C40 C41 -1.51(13) . . . . ? C39 C40 C41 C42 1.5(2) . . . . ? C35 C40 C41 C42 -176.17(12) . . . . ? C39 C40 C41 C46 178.83(12) . . . . ? C35 C40 C41 C46 1.14(13) . . . . ? C46 C41 C42 C43 -0.57(18) . . . . ? C40 C41 C42 C43 176.47(12) . . . . ? C41 C42 C43 C44 0.59(19) . . . . ? C42 C43 C44 C45 -0.1(2) . . . . ? C43 C44 C45 C46 -0.46(19) . . . . ? C44 C45 C46 C41 0.48(18) . . . . ? C44 C45 C46 C34 -176.28(11) . . . . ? C42 C41 C46 C45 0.04(17) . . . . ? C40 C41 C46 C45 -177.60(10) . . . . ? C42 C41 C46 C34 177.30(10) . . . . ? C40 C41 C46 C34 -0.33(12) . . . . ? O34 C34 C46 C45 62.54(15) . . . . ? C35 C34 C46 C45 176.49(11) . . . . ? C33 C34 C46 C45 -63.74(15) . . . . ? O34 C34 C46 C41 -114.47(10) . . . . ? C35 C34 C46 C41 -0.52(12) . . . . ? C33 C34 C46 C41 119.25(10) . . . . ? C6G N1G C2G C3G -0.5(2) . . . . ? C6G N1G C2G C7G 179.64(14) . . . . ? N1G C2G C3G C4G -0.3(2) . . . . ? C7G C2G C3G C4G 179.56(15) . . . . ? C2G C3G C4G C5G 0.6(2) . . . . ? C3G C4G C5G C6G -0.1(2) . . . . ? C2G N1G C6G C5G 1.0(2) . . . . ? C4G C5G C6G N1G -0.7(2) . . . . ? C13G N8G C9G C10G -0.6(2) . . . . ? C13G N8G C9G C14G 177.97(14) . . . . ? N8G C9G C10G C11G 0.9(2) . . . . ? C14G C9G C10G C11G -177.62(15) . . . . ? C9G C10G C11G C12G -0.5(2) . . . . ? C10G C11G C12G C13G -0.2(2) . . . . ? C9G N8G C13G C12G -0.1(2) . . . . ? C11G C12G C13G N8G 0.5(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O34 H34 O13 0.938(19) 1.788(19) 2.6843(12) 158.8(16) . O13 H13 N1G 0.944(18) 1.763(18) 2.7071(13) 179.5(17) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.242 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 945700' ####################################################################### # # 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_H.3PIC _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C46 H30 O2, 2(C6 H7 N)' _chemical_formula_sum 'C58 H44 N2 O2' _chemical_formula_weight 800.95 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c 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 16.6293(5) _cell_length_b 11.5306(2) _cell_length_c 22.3729(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.2300(10) _cell_angle_gamma 90.00 _cell_volume 4272.05(19) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 18333 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 27.10 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1688 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9815 _exptl_absorpt_correction_T_max 0.9933 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.0\% \f scans and \w scans' _diffrn_reflns_number 18333 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.0445 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 27.10 _reflns_number_total 9407 _reflns_number_gt 6272 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT program (Nonius, 2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _iucr_refine_instructions_details ; TITL data in P2(1)/c CELL 0.71073 16.6293 11.5306 22.3729 90.000 95.230 90.000 ZERR 4.0000 0.0005 0.0002 0.0006 0.000 0.001 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 232 176 8 8 MERG 2 FMAP 2 GRID PLAN 1 TEMP -100 SIZE 0.09 0.11 0.25 CONF BOND $H HTAB O34 O13 HTAB O13 N1G OMIT 1 0 0 OMIT -2 0 2 OMIT -1 1 1 OMIT 0 1 1 OMIT 1 1 0 OMIT 2 0 0 OMIT -1 0 2 OMIT 1 0 2 OMIT 0 0 2 OMIT 0 1 2 L.S. 20 ACTA WGHT 0.064400 0.073600 FVAR 0.25764 O13 4 0.206853 0.322150 0.092546 11.00000 0.02837 0.02289 = 0.03020 -0.00200 -0.00085 0.00207 H13 2 0.181464 0.273559 0.060180 11.00000 0.08306 O34 4 0.149062 0.428458 0.190433 11.00000 0.03186 0.02179 = 0.03183 0.00325 0.00659 0.00214 H34 2 0.159369 0.380254 0.155564 11.00000 0.07122 N1G 3 0.140848 0.191944 -0.005700 11.00000 0.03823 0.03885 = 0.03976 -0.00072 -0.00375 0.00178 N8G 3 0.478655 0.971381 0.408460 11.00000 0.03738 0.04944 = 0.04355 -0.00364 0.00907 -0.00210 C1 1 0.229030 0.148209 0.151294 11.00000 0.02584 0.02379 = 0.02696 -0.00032 0.00117 -0.00066 C2 1 0.174433 0.143161 0.194335 11.00000 0.03744 0.02671 = 0.03485 -0.00113 0.01135 0.00054 AFIX 43 H2 2 0.162300 0.210479 0.216287 11.00000 -1.20000 AFIX 0 C3 1 0.137666 0.037799 0.204863 11.00000 0.03971 0.03302 = 0.03709 0.00333 0.01207 -0.00335 AFIX 43 H3 2 0.099325 0.033482 0.233772 11.00000 -1.20000 AFIX 0 C4 1 0.156279 -0.061055 0.173680 11.00000 0.04349 0.02651 = 0.03702 0.00323 0.00347 -0.00856 AFIX 43 H4 2 0.130473 -0.132355 0.181304 11.00000 -1.20000 AFIX 0 C5 1 0.212181 -0.056706 0.131513 11.00000 0.04195 0.02372 = 0.03354 -0.00369 0.00229 -0.00131 AFIX 43 H5 2 0.225529 -0.124716 0.110581 11.00000 -1.20000 AFIX 0 C6 1 0.248434 0.048554 0.120283 11.00000 0.02774 0.02327 = 0.02491 -0.00046 -0.00011 0.00244 C7 1 0.307511 0.079148 0.077928 11.00000 0.02361 0.02617 = 0.02415 -0.00203 -0.00157 0.00287 C8 1 0.344472 0.011042 0.037150 11.00000 0.03038 0.03021 = 0.03094 -0.00509 -0.00074 0.00638 AFIX 43 H8 2 0.332781 -0.069421 0.033450 11.00000 -1.20000 AFIX 0 C9 1 0.398742 0.062829 0.001973 11.00000 0.03149 0.04295 = 0.03069 -0.00676 0.00575 0.00966 AFIX 43 H9 2 0.423519 0.017804 -0.026815 11.00000 -1.20000 AFIX 0 C10 1 0.417287 0.179816 0.008355 11.00000 0.03116 0.04745 = 0.03268 -0.00021 0.01054 0.00078 AFIX 43 H10 2 0.456123 0.213318 -0.015063 11.00000 -1.20000 AFIX 0 C11 1 0.379467 0.248911 0.048855 11.00000 0.03292 0.03247 = 0.03134 0.00000 0.00640 -0.00247 AFIX 43 H11 2 0.392028 0.329044 0.053018 11.00000 -1.20000 AFIX 0 C12 1 0.323690 0.198550 0.082562 11.00000 0.02420 0.02820 = 0.02377 -0.00123 0.00074 0.00134 C13 1 0.268912 0.255041 0.125702 11.00000 0.02601 0.02245 = 0.02606 -0.00024 0.00324 0.00127 C14 1 0.313947 0.333229 0.172438 11.00000 0.02288 0.02622 = 0.02545 -0.00203 0.00504 -0.00075 C15 1 0.360525 0.279483 0.218341 11.00000 0.02907 0.03004 = 0.03015 0.00283 0.00652 -0.00015 AFIX 43 H15 2 0.361435 0.197125 0.219367 11.00000 -1.20000 AFIX 0 C16 1 0.407183 0.340782 0.264137 11.00000 0.02467 0.04613 = 0.02564 0.00323 0.00588 -0.00238 C17 1 0.455412 0.285391 0.311442 11.00000 0.03451 0.06388 = 0.03245 0.01233 0.00169 -0.00453 AFIX 43 H17 2 0.457290 0.203121 0.313384 11.00000 -1.20000 AFIX 0 C18 1 0.499043 0.349619 0.354094 11.00000 0.03486 0.09640 = 0.03034 0.01247 -0.00378 -0.00554 AFIX 43 H18 2 0.531153 0.311699 0.385530 11.00000 -1.20000 AFIX 0 C19 1 0.496944 0.471359 0.351975 11.00000 0.03996 0.08906 = 0.03388 -0.01067 -0.00249 -0.01364 AFIX 43 H19 2 0.527389 0.514941 0.382158 11.00000 -1.20000 AFIX 0 C20 1 0.451871 0.527412 0.307253 11.00000 0.03604 0.06108 = 0.03982 -0.01459 -0.00035 -0.00939 AFIX 43 H20 2 0.451084 0.609777 0.306347 11.00000 -1.20000 AFIX 0 C21 1 0.405854 0.463537 0.261782 11.00000 0.02480 0.04485 = 0.02876 -0.00700 0.00344 -0.00479 C22 1 0.359041 0.517716 0.214345 11.00000 0.02718 0.02992 = 0.03826 -0.00738 0.00342 -0.00290 AFIX 43 H22 2 0.359289 0.600026 0.212508 11.00000 -1.20000 AFIX 0 C23 1 0.312789 0.458001 0.170338 11.00000 0.02155 0.02652 = 0.02942 -0.00295 0.00559 -0.00012 C24 1 0.271985 0.533208 0.121296 11.00000 0.02770 0.01863 = 0.02782 -0.00540 0.00237 -0.00242 C25 1 0.321111 0.572968 0.079317 11.00000 0.02704 0.02507 = 0.03833 -0.00449 0.00744 -0.00160 AFIX 43 H25 2 0.375067 0.545212 0.081138 11.00000 -1.20000 AFIX 0 C26 1 0.295293 0.652818 0.033778 11.00000 0.03601 0.02154 = 0.03078 -0.00473 0.00849 -0.00463 C27 1 0.345611 0.691240 -0.010260 11.00000 0.04623 0.02844 = 0.04132 -0.00662 0.01996 -0.00537 AFIX 43 H27 2 0.399548 0.663654 -0.009259 11.00000 -1.20000 AFIX 0 C28 1 0.317429 0.767294 -0.053991 11.00000 0.06298 0.03113 = 0.03487 -0.00404 0.02190 -0.01129 AFIX 43 H28 2 0.351362 0.790875 -0.083699 11.00000 -1.20000 AFIX 0 C29 1 0.238058 0.811006 -0.055217 11.00000 0.06309 0.03112 = 0.02986 0.00214 0.00423 -0.00870 AFIX 43 H29 2 0.218916 0.864423 -0.085571 11.00000 -1.20000 AFIX 0 C30 1 0.188763 0.777028 -0.013123 11.00000 0.04035 0.02944 = 0.03289 0.00216 -0.00029 -0.00472 AFIX 43 H30 2 0.135654 0.807770 -0.014143 11.00000 -1.20000 AFIX 0 C31 1 0.215625 0.696301 0.032268 11.00000 0.03315 0.02214 = 0.02764 -0.00404 0.00174 -0.00572 C32 1 0.166056 0.656355 0.076205 11.00000 0.02654 0.02269 = 0.03023 -0.00236 0.00262 -0.00181 AFIX 43 H32 2 0.112891 0.686682 0.075793 11.00000 -1.20000 AFIX 0 C33 1 0.190796 0.576046 0.119403 11.00000 0.02481 0.02048 = 0.02540 -0.00439 0.00272 -0.00250 C34 1 0.128723 0.537709 0.162665 11.00000 0.02690 0.02002 = 0.02561 0.00017 0.00432 0.00092 C35 1 0.043574 0.532170 0.131158 11.00000 0.02761 0.02486 = 0.02549 0.00498 0.00453 -0.00374 C36 1 0.015990 0.464307 0.082670 11.00000 0.03414 0.03357 = 0.02915 -0.00063 0.00441 -0.00781 AFIX 43 H36 2 0.051948 0.415531 0.063596 11.00000 -1.20000 AFIX 0 C37 1 -0.065203 0.468883 0.062451 11.00000 0.03807 0.04829 = 0.03126 0.00502 -0.00309 -0.01704 AFIX 43 H37 2 -0.085084 0.422810 0.029125 11.00000 -1.20000 AFIX 0 C38 1 -0.117802 0.539916 0.090280 11.00000 0.02684 0.05342 = 0.04703 0.01636 -0.00334 -0.00647 AFIX 43 H38 2 -0.173372 0.541418 0.076000 11.00000 -1.20000 AFIX 0 C39 1 -0.090316 0.608717 0.138650 11.00000 0.02885 0.03678 = 0.04770 0.01166 0.00814 0.00279 AFIX 43 H39 2 -0.126470 0.657489 0.157533 11.00000 -1.20000 AFIX 0 C40 1 -0.008893 0.605069 0.159035 11.00000 0.02729 0.02551 = 0.03325 0.00713 0.00792 -0.00066 C41 1 0.037628 0.665708 0.208621 11.00000 0.03080 0.02252 = 0.03160 0.00429 0.01079 -0.00085 C42 1 0.014704 0.748572 0.248932 11.00000 0.04012 0.02788 = 0.04776 0.00086 0.02269 0.00183 AFIX 43 H42 2 -0.039134 0.776970 0.246155 11.00000 -1.20000 AFIX 0 C43 1 0.071377 0.789088 0.293136 11.00000 0.06234 0.02987 = 0.03634 -0.00844 0.02334 -0.00427 AFIX 43 H43 2 0.056024 0.844837 0.321222 11.00000 -1.20000 AFIX 0 C44 1 0.150100 0.749314 0.296868 11.00000 0.05964 0.03318 = 0.02630 -0.00281 0.00526 -0.00585 AFIX 43 H44 2 0.188355 0.778245 0.327369 11.00000 -1.20000 AFIX 0 C45 1 0.173859 0.667204 0.256321 11.00000 0.04048 0.02775 = 0.02846 0.00021 0.00256 -0.00033 AFIX 43 H45 2 0.227975 0.639936 0.258953 11.00000 -1.20000 AFIX 0 C46 1 0.117676 0.626189 0.212367 11.00000 0.03373 0.02165 = 0.02354 0.00156 0.00752 -0.00188 C2G 1 0.190520 0.172431 -0.048177 11.00000 0.03972 0.03149 = 0.03569 0.00297 -0.00355 0.00130 AFIX 43 H2G 2 0.244599 0.198886 -0.040660 11.00000 -1.20000 AFIX 0 C3G 1 0.169947 0.116823 -0.102369 11.00000 0.05963 0.03005 = 0.03639 0.00297 -0.00459 0.00225 C4G 1 0.091480 0.077215 -0.111496 11.00000 0.07152 0.04609 = 0.04703 -0.00534 -0.01790 -0.00744 AFIX 43 H4G 2 0.073993 0.037332 -0.147508 11.00000 -1.20000 AFIX 0 C5G 1 0.038442 0.095251 -0.068637 11.00000 0.04721 0.06891 = 0.07198 -0.00157 -0.01439 -0.01758 AFIX 43 H5G 2 -0.015666 0.068301 -0.074786 11.00000 -1.20000 AFIX 0 C6G 1 0.065391 0.153623 -0.016145 11.00000 0.03882 0.06260 = 0.05729 -0.00488 -0.00047 -0.00297 AFIX 43 H6G 2 0.028621 0.166565 0.013267 11.00000 -1.20000 AFIX 0 C7G 1 0.230299 0.102728 -0.147694 11.00000 0.09449 0.05233 = 0.04338 -0.00182 0.01480 0.00363 AFIX 137 H7B 2 0.269636 0.042960 -0.133979 11.00000 -1.50000 H7A 2 0.258336 0.176463 -0.152420 11.00000 -1.50000 H7C 2 0.202378 0.079546 -0.186313 11.00000 -1.50000 AFIX 0 C9G 1 0.454515 0.924244 0.355653 11.00000 0.03440 0.04748 = 0.04446 -0.00264 0.01383 0.00040 AFIX 43 H9G 2 0.490491 0.871914 0.338944 11.00000 -1.20000 AFIX 0 C10G 1 0.381036 0.945274 0.322957 11.00000 0.03449 0.04639 = 0.04242 0.00178 0.00911 -0.00727 C11G 1 0.330054 1.021991 0.348164 11.00000 0.03648 0.05129 = 0.06122 0.00592 0.00247 0.00442 AFIX 43 H11G 2 0.278771 1.039546 0.327948 11.00000 -1.20000 AFIX 0 C12G 1 0.353591 1.073147 0.402705 11.00000 0.05042 0.04251 = 0.06562 -0.00712 0.01509 0.00631 AFIX 43 H12G 2 0.319247 1.126654 0.420286 11.00000 -1.20000 AFIX 0 C13G 1 0.427661 1.045046 0.430976 11.00000 0.04616 0.04190 = 0.04524 -0.00259 0.01229 -0.00327 AFIX 43 H13G 2 0.443442 1.080037 0.468670 11.00000 -1.20000 AFIX 0 C14G 1 0.359199 0.887760 0.263731 11.00000 0.05387 0.08999 = 0.05318 -0.01308 0.00209 -0.00946 AFIX 137 H14B 2 0.326315 0.818877 0.269625 11.00000 -1.50000 H14A 2 0.408560 0.864764 0.246019 11.00000 -1.50000 H14C 2 0.328423 0.941976 0.236766 11.00000 -1.50000 HKLF 4 END ; _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^)+(0.0644P)^2^+0.0736P] 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_number_reflns 9407 _refine_ls_number_parameters 569 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0797 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1193 _refine_ls_wR_factor_gt 0.1053 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 O13 O 0.20685(5) 0.32215(8) 0.09255(4) 0.0274(2) Uani 1 1 d . . . H13 H 0.1815(12) 0.2736(17) 0.0602(9) 0.083(7) Uiso 1 1 d . . . O34 O 0.14906(6) 0.42846(8) 0.19043(4) 0.0283(2) Uani 1 1 d . . . H34 H 0.1594(11) 0.3803(17) 0.1556(9) 0.071(6) Uiso 1 1 d . . . N1G N 0.14085(8) 0.19194(11) -0.00570(6) 0.0394(3) Uani 1 1 d . . . N8G N 0.47865(8) 0.97138(12) 0.40846(6) 0.0431(3) Uani 1 1 d . . . C1 C 0.22903(8) 0.14821(11) 0.15129(6) 0.0256(3) Uani 1 1 d . . . C2 C 0.17443(9) 0.14316(12) 0.19433(6) 0.0325(3) Uani 1 1 d . . . H2 H 0.1623 0.2105 0.2163 0.039 Uiso 1 1 calc R . . C3 C 0.13767(9) 0.03780(12) 0.20486(7) 0.0361(4) Uani 1 1 d . . . H3 H 0.0993 0.0335 0.2338 0.043 Uiso 1 1 calc R . . C4 C 0.15628(9) -0.06105(13) 0.17368(7) 0.0357(4) Uani 1 1 d . . . H4 H 0.1305 -0.1324 0.1813 0.043 Uiso 1 1 calc R . . C5 C 0.21218(9) -0.05671(12) 0.13151(7) 0.0331(3) Uani 1 1 d . . . H5 H 0.2255 -0.1247 0.1106 0.040 Uiso 1 1 calc R . . C6 C 0.24843(8) 0.04855(11) 0.12028(6) 0.0255(3) Uani 1 1 d . . . C7 C 0.30751(8) 0.07915(11) 0.07793(6) 0.0249(3) Uani 1 1 d . . . C8 C 0.34447(8) 0.01104(13) 0.03715(6) 0.0307(3) Uani 1 1 d . . . H8 H 0.3328 -0.0694 0.0335 0.037 Uiso 1 1 calc R . . C9 C 0.39874(9) 0.06283(13) 0.00197(7) 0.0349(4) Uani 1 1 d . . . H9 H 0.4235 0.0178 -0.0268 0.042 Uiso 1 1 calc R . . C10 C 0.41729(9) 0.17982(13) 0.00836(7) 0.0366(4) Uani 1 1 d . . . H10 H 0.4561 0.2133 -0.0151 0.044 Uiso 1 1 calc R . . C11 C 0.37947(8) 0.24891(13) 0.04885(6) 0.0320(3) Uani 1 1 d . . . H11 H 0.3920 0.3290 0.0530 0.038 Uiso 1 1 calc R . . C12 C 0.32369(8) 0.19855(11) 0.08256(6) 0.0255(3) Uani 1 1 d . . . C13 C 0.26891(8) 0.25504(11) 0.12570(6) 0.0248(3) Uani 1 1 d . . . C14 C 0.31395(8) 0.33323(11) 0.17244(6) 0.0247(3) Uani 1 1 d . . . C15 C 0.36053(8) 0.27948(12) 0.21834(6) 0.0295(3) Uani 1 1 d . . . H15 H 0.3614 0.1971 0.2194 0.035 Uiso 1 1 calc R . . C16 C 0.40718(8) 0.34078(13) 0.26414(6) 0.0319(3) Uani 1 1 d . . . C17 C 0.45541(9) 0.28539(16) 0.31144(7) 0.0437(4) Uani 1 1 d . . . H17 H 0.4573 0.2031 0.3134 0.052 Uiso 1 1 calc R . . C18 C 0.49904(10) 0.34962(19) 0.35409(7) 0.0543(5) Uani 1 1 d . . . H18 H 0.5312 0.3117 0.3855 0.065 Uiso 1 1 calc R . . C19 C 0.49694(10) 0.47136(19) 0.35198(8) 0.0547(5) Uani 1 1 d . . . H19 H 0.5274 0.5149 0.3822 0.066 Uiso 1 1 calc R . . C20 C 0.45187(9) 0.52741(16) 0.30725(7) 0.0459(4) Uani 1 1 d . . . H20 H 0.4511 0.6098 0.3063 0.055 Uiso 1 1 calc R . . C21 C 0.40585(8) 0.46354(13) 0.26178(6) 0.0327(3) Uani 1 1 d . . . C22 C 0.35904(8) 0.51772(13) 0.21434(6) 0.0318(3) Uani 1 1 d . . . H22 H 0.3593 0.6000 0.2125 0.038 Uiso 1 1 calc R . . C23 C 0.31279(8) 0.45800(11) 0.17034(6) 0.0256(3) Uani 1 1 d . . . C24 C 0.27198(8) 0.53321(11) 0.12130(6) 0.0247(3) Uani 1 1 d . . . C25 C 0.32111(8) 0.57297(12) 0.07932(6) 0.0299(3) Uani 1 1 d . . . H25 H 0.3751 0.5452 0.0811 0.036 Uiso 1 1 calc R . . C26 C 0.29529(8) 0.65282(12) 0.03378(6) 0.0291(3) Uani 1 1 d . . . C27 C 0.34561(10) 0.69124(12) -0.01026(7) 0.0377(4) Uani 1 1 d . . . H27 H 0.3995 0.6637 -0.0093 0.045 Uiso 1 1 calc R . . C28 C 0.31743(11) 0.76729(13) -0.05399(7) 0.0419(4) Uani 1 1 d . . . H28 H 0.3514 0.7909 -0.0837 0.050 Uiso 1 1 calc R . . C29 C 0.23806(10) 0.81101(13) -0.05522(7) 0.0414(4) Uani 1 1 d . . . H29 H 0.2189 0.8644 -0.0856 0.050 Uiso 1 1 calc R . . C30 C 0.18876(9) 0.77703(12) -0.01312(6) 0.0344(4) Uani 1 1 d . . . H30 H 0.1357 0.8078 -0.0141 0.041 Uiso 1 1 calc R . . C31 C 0.21562(8) 0.69630(11) 0.03227(6) 0.0277(3) Uani 1 1 d . . . C32 C 0.16606(8) 0.65635(11) 0.07621(6) 0.0265(3) Uani 1 1 d . . . H32 H 0.1129 0.6867 0.0758 0.032 Uiso 1 1 calc R . . C33 C 0.19080(8) 0.57605(11) 0.11940(6) 0.0235(3) Uani 1 1 d . . . C34 C 0.12872(8) 0.53771(11) 0.16267(6) 0.0241(3) Uani 1 1 d . . . C35 C 0.04357(8) 0.53217(11) 0.13116(6) 0.0259(3) Uani 1 1 d . . . C36 C 0.01599(9) 0.46431(12) 0.08267(6) 0.0322(3) Uani 1 1 d . . . H36 H 0.0519 0.4155 0.0636 0.039 Uiso 1 1 calc R . . C37 C -0.06520(9) 0.46888(14) 0.06245(7) 0.0396(4) Uani 1 1 d . . . H37 H -0.0851 0.4228 0.0291 0.048 Uiso 1 1 calc R . . C38 C -0.11780(9) 0.53992(14) 0.09028(7) 0.0428(4) Uani 1 1 d . . . H38 H -0.1734 0.5414 0.0760 0.051 Uiso 1 1 calc R . . C39 C -0.09032(9) 0.60872(13) 0.13865(7) 0.0375(4) Uani 1 1 d . . . H39 H -0.1265 0.6575 0.1575 0.045 Uiso 1 1 calc R . . C40 C -0.00889(8) 0.60507(11) 0.15903(6) 0.0284(3) Uani 1 1 d . . . C41 C 0.03763(8) 0.66571(11) 0.20862(6) 0.0278(3) Uani 1 1 d . . . C42 C 0.01470(9) 0.74857(13) 0.24893(7) 0.0374(4) Uani 1 1 d . . . H42 H -0.0391 0.7770 0.2462 0.045 Uiso 1 1 calc R . . C43 C 0.07138(10) 0.78909(13) 0.29314(7) 0.0417(4) Uani 1 1 d . . . H43 H 0.0560 0.8448 0.3212 0.050 Uiso 1 1 calc R . . C44 C 0.15010(10) 0.74931(13) 0.29687(7) 0.0396(4) Uani 1 1 d . . . H44 H 0.1884 0.7782 0.3274 0.048 Uiso 1 1 calc R . . C45 C 0.17386(9) 0.66720(12) 0.25632(6) 0.0323(3) Uani 1 1 d . . . H45 H 0.2280 0.6399 0.2590 0.039 Uiso 1 1 calc R . . C46 C 0.11768(8) 0.62619(11) 0.21237(6) 0.0260(3) Uani 1 1 d . . . C2G C 0.19052(9) 0.17243(12) -0.04818(7) 0.0361(4) Uani 1 1 d . . . H2G H 0.2446 0.1989 -0.0407 0.043 Uiso 1 1 calc R . . C3G C 0.16995(11) 0.11682(13) -0.10237(7) 0.0426(4) Uani 1 1 d . . . C4G C 0.09148(12) 0.07721(15) -0.11150(9) 0.0563(5) Uani 1 1 d . . . H4G H 0.0740 0.0373 -0.1475 0.068 Uiso 1 1 calc R . . C5G C 0.03844(12) 0.09525(18) -0.06864(10) 0.0639(6) Uani 1 1 d . . . H5G H -0.0157 0.0683 -0.0748 0.077 Uiso 1 1 calc R . . C6G C 0.06539(10) 0.15362(16) -0.01614(8) 0.0532(5) Uani 1 1 d . . . H6G H 0.0286 0.1666 0.0133 0.064 Uiso 1 1 calc R . . C7G C 0.23030(13) 0.10273(16) -0.14769(8) 0.0629(5) Uani 1 1 d . . . H7B H 0.2696 0.0430 -0.1340 0.094 Uiso 1 1 calc R . . H7A H 0.2583 0.1765 -0.1524 0.094 Uiso 1 1 calc R . . H7C H 0.2024 0.0795 -0.1863 0.094 Uiso 1 1 calc R . . C9G C 0.45452(9) 0.92424(14) 0.35565(7) 0.0415(4) Uani 1 1 d . . . H9G H 0.4905 0.8719 0.3389 0.050 Uiso 1 1 calc R . . C10G C 0.38104(9) 0.94527(14) 0.32296(7) 0.0408(4) Uani 1 1 d . . . C11G C 0.33005(10) 1.02199(15) 0.34816(8) 0.0498(4) Uani 1 1 d . . . H11G H 0.2788 1.0395 0.3279 0.060 Uiso 1 1 calc R . . C12G C 0.35359(11) 1.07315(15) 0.40270(9) 0.0522(5) Uani 1 1 d . . . H12G H 0.3192 1.1267 0.4203 0.063 Uiso 1 1 calc R . . C13G C 0.42766(10) 1.04505(14) 0.43098(8) 0.0439(4) Uani 1 1 d . . . H13G H 0.4434 1.0800 0.4687 0.053 Uiso 1 1 calc R . . C14G C 0.35920(12) 0.88776(19) 0.26373(8) 0.0658(6) Uani 1 1 d . . . H14B H 0.3263 0.8189 0.2696 0.099 Uiso 1 1 calc R . . H14A H 0.4086 0.8648 0.2460 0.099 Uiso 1 1 calc R . . H14C H 0.3284 0.9420 0.2368 0.099 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 O13 0.0284(5) 0.0229(5) 0.0302(5) -0.0020(4) -0.0009(4) 0.0021(4) O34 0.0319(5) 0.0218(5) 0.0318(6) 0.0032(4) 0.0066(4) 0.0021(4) N1G 0.0382(8) 0.0389(8) 0.0398(8) -0.0007(6) -0.0038(6) 0.0018(6) N8G 0.0374(8) 0.0494(8) 0.0436(8) -0.0036(7) 0.0091(7) -0.0021(6) C1 0.0258(7) 0.0238(7) 0.0270(7) -0.0003(6) 0.0012(6) -0.0007(6) C2 0.0374(8) 0.0267(7) 0.0348(8) -0.0011(7) 0.0114(7) 0.0005(6) C3 0.0397(9) 0.0330(8) 0.0371(9) 0.0033(7) 0.0121(7) -0.0034(7) C4 0.0435(9) 0.0265(8) 0.0370(9) 0.0032(7) 0.0035(7) -0.0086(7) C5 0.0420(9) 0.0237(7) 0.0335(8) -0.0037(6) 0.0023(7) -0.0013(6) C6 0.0277(8) 0.0233(7) 0.0249(7) -0.0005(6) -0.0001(6) 0.0024(6) C7 0.0236(7) 0.0262(7) 0.0241(7) -0.0020(6) -0.0016(6) 0.0029(6) C8 0.0304(8) 0.0302(8) 0.0309(8) -0.0051(6) -0.0007(6) 0.0064(6) C9 0.0315(8) 0.0429(9) 0.0307(8) -0.0068(7) 0.0057(7) 0.0097(7) C10 0.0312(8) 0.0474(10) 0.0327(8) -0.0002(7) 0.0105(7) 0.0008(7) C11 0.0329(8) 0.0325(8) 0.0313(8) 0.0000(7) 0.0064(7) -0.0025(6) C12 0.0242(7) 0.0282(7) 0.0238(7) -0.0012(6) 0.0007(6) 0.0013(6) C13 0.0260(7) 0.0225(7) 0.0261(7) -0.0002(6) 0.0032(6) 0.0013(6) C14 0.0229(7) 0.0262(7) 0.0254(7) -0.0020(6) 0.0050(6) -0.0008(6) C15 0.0291(8) 0.0300(8) 0.0301(8) 0.0028(6) 0.0065(6) -0.0001(6) C16 0.0247(8) 0.0461(9) 0.0256(7) 0.0032(7) 0.0059(6) -0.0024(7) C17 0.0345(9) 0.0639(11) 0.0325(8) 0.0123(8) 0.0017(7) -0.0045(8) C18 0.0349(9) 0.0964(16) 0.0303(9) 0.0125(10) -0.0038(8) -0.0055(10) C19 0.0400(10) 0.0891(15) 0.0339(10) -0.0107(10) -0.0025(8) -0.0136(10) C20 0.0360(9) 0.0611(11) 0.0398(9) -0.0146(9) -0.0003(8) -0.0094(8) C21 0.0248(8) 0.0448(9) 0.0288(8) -0.0070(7) 0.0034(6) -0.0048(7) C22 0.0272(8) 0.0299(8) 0.0383(8) -0.0074(7) 0.0034(7) -0.0029(6) C23 0.0216(7) 0.0265(7) 0.0294(7) -0.0030(6) 0.0056(6) -0.0001(6) C24 0.0277(7) 0.0186(7) 0.0278(7) -0.0054(6) 0.0024(6) -0.0024(5) C25 0.0270(8) 0.0251(7) 0.0383(8) -0.0045(7) 0.0074(7) -0.0016(6) C26 0.0360(8) 0.0215(7) 0.0308(8) -0.0047(6) 0.0085(6) -0.0046(6) C27 0.0462(9) 0.0284(8) 0.0413(9) -0.0066(7) 0.0200(8) -0.0054(7) C28 0.0630(11) 0.0311(8) 0.0349(9) -0.0040(7) 0.0219(8) -0.0113(8) C29 0.0631(11) 0.0311(8) 0.0299(8) 0.0021(7) 0.0042(8) -0.0087(8) C30 0.0403(9) 0.0294(8) 0.0329(8) 0.0022(7) -0.0003(7) -0.0047(7) C31 0.0331(8) 0.0221(7) 0.0276(7) -0.0040(6) 0.0017(6) -0.0057(6) C32 0.0265(7) 0.0227(7) 0.0302(8) -0.0024(6) 0.0026(6) -0.0018(6) C33 0.0248(7) 0.0205(7) 0.0254(7) -0.0044(6) 0.0027(6) -0.0025(5) C34 0.0269(7) 0.0200(7) 0.0256(7) 0.0002(6) 0.0043(6) 0.0009(5) C35 0.0276(7) 0.0249(7) 0.0255(7) 0.0050(6) 0.0045(6) -0.0037(6) C36 0.0341(8) 0.0336(8) 0.0291(8) -0.0006(6) 0.0044(7) -0.0078(6) C37 0.0381(9) 0.0483(10) 0.0313(8) 0.0050(7) -0.0031(7) -0.0170(8) C38 0.0268(8) 0.0534(10) 0.0470(10) 0.0164(8) -0.0033(8) -0.0065(8) C39 0.0288(8) 0.0368(9) 0.0477(10) 0.0117(8) 0.0081(7) 0.0028(7) C40 0.0273(8) 0.0255(7) 0.0333(8) 0.0071(6) 0.0079(6) -0.0007(6) C41 0.0308(8) 0.0225(7) 0.0316(8) 0.0043(6) 0.0108(6) -0.0008(6) C42 0.0401(9) 0.0279(8) 0.0478(10) 0.0009(7) 0.0227(8) 0.0018(7) C43 0.0623(11) 0.0299(8) 0.0363(9) -0.0084(7) 0.0233(8) -0.0043(8) C44 0.0596(11) 0.0332(9) 0.0263(8) -0.0028(7) 0.0053(8) -0.0058(8) C45 0.0405(9) 0.0278(8) 0.0285(8) 0.0002(6) 0.0026(7) -0.0003(7) C46 0.0337(8) 0.0217(7) 0.0235(7) 0.0016(6) 0.0075(6) -0.0019(6) C2G 0.0397(9) 0.0315(8) 0.0357(9) 0.0030(7) -0.0035(7) 0.0013(7) C3G 0.0596(11) 0.0300(8) 0.0364(9) 0.0030(7) -0.0046(8) 0.0023(8) C4G 0.0715(14) 0.0461(10) 0.0470(11) -0.0053(9) -0.0179(10) -0.0074(10) C5G 0.0472(11) 0.0689(13) 0.0720(14) -0.0016(11) -0.0144(11) -0.0176(10) C6G 0.0388(10) 0.0626(12) 0.0573(11) -0.0049(10) -0.0005(9) -0.0030(9) C7G 0.0945(16) 0.0523(11) 0.0434(11) -0.0018(9) 0.0148(11) 0.0036(11) C9G 0.0344(9) 0.0475(10) 0.0445(10) -0.0026(8) 0.0138(8) 0.0004(7) C10G 0.0345(9) 0.0464(10) 0.0424(9) 0.0018(8) 0.0091(8) -0.0073(7) C11G 0.0365(10) 0.0513(11) 0.0612(12) 0.0059(9) 0.0025(9) 0.0044(8) C12G 0.0504(11) 0.0425(10) 0.0656(13) -0.0071(9) 0.0151(10) 0.0063(8) C13G 0.0462(10) 0.0419(10) 0.0452(10) -0.0026(8) 0.0123(8) -0.0033(8) C14G 0.0539(12) 0.0900(16) 0.0532(12) -0.0131(11) 0.0021(10) -0.0095(11) _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 O13 C13 1.4403(15) . ? O13 H13 0.98(2) . ? O34 C34 1.4314(15) . ? O34 H34 0.99(2) . ? N1G C6G 1.331(2) . ? N1G C2G 1.3338(18) . ? N8G C9G 1.329(2) . ? N8G C13G 1.331(2) . ? C1 C2 1.3836(18) . ? C1 C6 1.3952(18) . ? C1 C13 1.5344(18) . ? C2 C3 1.390(2) . ? C2 H2 0.9500 . ? C3 C4 1.386(2) . ? C3 H3 0.9500 . ? C4 C5 1.384(2) . ? C4 H4 0.9500 . ? C5 C6 1.3883(19) . ? C5 H5 0.9500 . ? C6 C7 1.4688(18) . ? C7 C8 1.3889(18) . ? C7 C12 1.4048(18) . ? C8 C9 1.386(2) . ? C8 H8 0.9500 . ? C9 C10 1.388(2) . ? C9 H9 0.9500 . ? C10 C11 1.398(2) . ? C10 H10 0.9500 . ? C11 C12 1.3761(18) . ? C11 H11 0.9500 . ? C12 C13 1.5316(18) . ? C13 C14 1.5245(18) . ? C14 C15 1.3761(18) . ? C14 C23 1.4395(19) . ? C15 C16 1.4165(19) . ? C15 H15 0.9500 . ? C16 C21 1.417(2) . ? C16 C17 1.420(2) . ? C17 C18 1.364(2) . ? C17 H17 0.9500 . ? C18 C19 1.405(3) . ? C18 H18 0.9500 . ? C19 C20 1.358(2) . ? C19 H19 0.9500 . ? C20 C21 1.422(2) . ? C20 H20 0.9500 . ? C21 C22 1.404(2) . ? C22 C23 1.3773(18) . ? C22 H22 0.9500 . ? C23 C24 1.5101(19) . ? C24 C25 1.3782(18) . ? C24 C33 1.4346(18) . ? C25 C26 1.4108(19) . ? C25 H25 0.9500 . ? C26 C31 1.4140(19) . ? C26 C27 1.4204(19) . ? C27 C28 1.365(2) . ? C27 H27 0.9500 . ? C28 C29 1.411(2) . ? C28 H28 0.9500 . ? C29 C30 1.361(2) . ? C29 H29 0.9500 . ? C30 C31 1.4194(19) . ? C30 H30 0.9500 . ? C31 C32 1.4162(18) . ? C32 C33 1.3741(18) . ? C32 H32 0.9500 . ? C33 C34 1.5427(18) . ? C34 C35 1.5244(19) . ? C34 C46 1.5324(18) . ? C35 C36 1.3816(19) . ? C35 C40 1.3986(19) . ? C36 C37 1.385(2) . ? C36 H36 0.9500 . ? C37 C38 1.387(2) . ? C37 H37 0.9500 . ? C38 C39 1.385(2) . ? C38 H38 0.9500 . ? C39 C40 1.389(2) . ? C39 H39 0.9500 . ? C40 C41 1.4702(19) . ? C41 C42 1.391(2) . ? C41 C46 1.4022(19) . ? C42 C43 1.384(2) . ? C42 H42 0.9500 . ? C43 C44 1.382(2) . ? C43 H43 0.9500 . ? C44 C45 1.393(2) . ? C44 H44 0.9500 . ? C45 C46 1.3770(19) . ? C45 H45 0.9500 . ? C2G C3G 1.387(2) . ? C2G H2G 0.9500 . ? C3G C4G 1.380(2) . ? C3G C7G 1.499(2) . ? C4G C5G 1.377(3) . ? C4G H4G 0.9500 . ? C5G C6G 1.392(3) . ? C5G H5G 0.9500 . ? C6G H6G 0.9500 . ? C7G H7B 0.9800 . ? C7G H7A 0.9800 . ? C7G H7C 0.9800 . ? C9G C10G 1.387(2) . ? C9G H9G 0.9500 . ? C10G C11G 1.381(2) . ? C10G C14G 1.497(2) . ? C11G C12G 1.380(2) . ? C11G H11G 0.9500 . ? C12G C13G 1.371(2) . ? C12G H12G 0.9500 . ? C13G H13G 0.9500 . ? C14G H14B 0.9800 . ? C14G H14A 0.9800 . ? C14G H14C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O13 H13 108.3(11) . . ? C34 O34 H34 101.8(11) . . ? C6G N1G C2G 117.01(14) . . ? C9G N8G C13G 116.50(14) . . ? C2 C1 C6 120.50(12) . . ? C2 C1 C13 128.82(12) . . ? C6 C1 C13 110.38(11) . . ? C1 C2 C3 118.78(13) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C4 C3 C2 120.78(14) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C5 C4 C3 120.52(13) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 118.99(13) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C5 C6 C1 120.40(13) . . ? C5 C6 C7 130.83(13) . . ? C1 C6 C7 108.76(11) . . ? C8 C7 C12 120.62(13) . . ? C8 C7 C6 130.55(13) . . ? C12 C7 C6 108.82(11) . . ? C9 C8 C7 118.66(13) . . ? C9 C8 H8 120.7 . . ? C7 C8 H8 120.7 . . ? C8 C9 C10 120.69(13) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C9 C10 C11 120.76(14) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 118.69(13) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C11 C12 C7 120.48(12) . . ? C11 C12 C13 129.43(12) . . ? C7 C12 C13 110.02(11) . . ? O13 C13 C14 108.64(10) . . ? O13 C13 C12 110.08(10) . . ? C14 C13 C12 113.61(10) . . ? O13 C13 C1 108.04(10) . . ? C14 C13 C1 114.89(11) . . ? C12 C13 C1 101.29(10) . . ? C15 C14 C23 118.65(12) . . ? C15 C14 C13 116.96(12) . . ? C23 C14 C13 124.36(11) . . ? C14 C15 C16 123.30(13) . . ? C14 C15 H15 118.3 . . ? C16 C15 H15 118.3 . . ? C15 C16 C21 117.78(13) . . ? C15 C16 C17 123.34(15) . . ? C21 C16 C17 118.88(14) . . ? C18 C17 C16 120.37(17) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C17 C18 C19 120.60(16) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C20 C19 C18 120.72(16) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C19 C20 C21 120.37(17) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C22 C21 C16 118.58(13) . . ? C22 C21 C20 122.38(15) . . ? C16 C21 C20 119.05(14) . . ? C23 C22 C21 123.56(13) . . ? C23 C22 H22 118.2 . . ? C21 C22 H22 118.2 . . ? C22 C23 C14 118.12(12) . . ? C22 C23 C24 114.64(12) . . ? C14 C23 C24 126.97(12) . . ? C25 C24 C33 118.69(12) . . ? C25 C24 C23 115.54(12) . . ? C33 C24 C23 125.34(12) . . ? C24 C25 C26 123.30(13) . . ? C24 C25 H25 118.4 . . ? C26 C25 H25 118.4 . . ? C25 C26 C31 118.13(12) . . ? C25 C26 C27 123.01(13) . . ? C31 C26 C27 118.86(13) . . ? C28 C27 C26 120.81(14) . . ? C28 C27 H27 119.6 . . ? C26 C27 H27 119.6 . . ? C27 C28 C29 120.20(14) . . ? C27 C28 H28 119.9 . . ? C29 C28 H28 119.9 . . ? C30 C29 C28 120.33(15) . . ? C30 C29 H29 119.8 . . ? C28 C29 H29 119.8 . . ? C29 C30 C31 120.91(14) . . ? C29 C30 H30 119.5 . . ? C31 C30 H30 119.5 . . ? C26 C31 C32 118.13(12) . . ? C26 C31 C30 118.86(13) . . ? C32 C31 C30 123.01(13) . . ? C33 C32 C31 123.47(12) . . ? C33 C32 H32 118.3 . . ? C31 C32 H32 118.3 . . ? C32 C33 C24 118.26(12) . . ? C32 C33 C34 117.38(11) . . ? C24 C33 C34 124.37(11) . . ? O34 C34 C35 109.67(10) . . ? O34 C34 C46 108.07(10) . . ? C35 C34 C46 101.29(10) . . ? O34 C34 C33 112.29(10) . . ? C35 C34 C33 111.61(11) . . ? C46 C34 C33 113.32(10) . . ? C36 C35 C40 120.97(13) . . ? C36 C35 C34 127.93(13) . . ? C40 C35 C34 111.07(12) . . ? C35 C36 C37 118.61(14) . . ? C35 C36 H36 120.7 . . ? C37 C36 H36 120.7 . . ? C36 C37 C38 120.78(15) . . ? C36 C37 H37 119.6 . . ? C38 C37 H37 119.6 . . ? C39 C38 C37 120.82(14) . . ? C39 C38 H38 119.6 . . ? C37 C38 H38 119.6 . . ? C38 C39 C40 118.77(14) . . ? C38 C39 H39 120.6 . . ? C40 C39 H39 120.6 . . ? C39 C40 C35 120.05(14) . . ? C39 C40 C41 131.55(13) . . ? C35 C40 C41 108.40(11) . . ? C42 C41 C46 119.95(13) . . ? C42 C41 C40 131.27(13) . . ? C46 C41 C40 108.78(12) . . ? C43 C42 C41 119.10(14) . . ? C43 C42 H42 120.4 . . ? C41 C42 H42 120.4 . . ? C44 C43 C42 120.71(14) . . ? C44 C43 H43 119.6 . . ? C42 C43 H43 119.6 . . ? C43 C44 C45 120.62(14) . . ? C43 C44 H44 119.7 . . ? C45 C44 H44 119.7 . . ? C46 C45 C44 118.96(14) . . ? C46 C45 H45 120.5 . . ? C44 C45 H45 120.5 . . ? C45 C46 C41 120.64(13) . . ? C45 C46 C34 128.94(12) . . ? C41 C46 C34 110.42(12) . . ? N1G C2G C3G 125.56(15) . . ? N1G C2G H2G 117.2 . . ? C3G C2G H2G 117.2 . . ? C4G C3G C2G 115.91(17) . . ? C4G C3G C7G 123.11(16) . . ? C2G C3G C7G 120.97(16) . . ? C5G C4G C3G 120.28(17) . . ? C5G C4G H4G 119.9 . . ? C3G C4G H4G 119.9 . . ? C4G C5G C6G 118.91(17) . . ? C4G C5G H5G 120.5 . . ? C6G C5G H5G 120.5 . . ? N1G C6G C5G 122.32(18) . . ? N1G C6G H6G 118.8 . . ? C5G C6G H6G 118.8 . . ? C3G C7G H7B 109.5 . . ? C3G C7G H7A 109.5 . . ? H7B C7G H7A 109.5 . . ? C3G C7G H7C 109.5 . . ? H7B C7G H7C 109.5 . . ? H7A C7G H7C 109.5 . . ? N8G C9G C10G 125.28(15) . . ? N8G C9G H9G 117.4 . . ? C10G C9G H9G 117.4 . . ? C11G C10G C9G 116.15(15) . . ? C11G C10G C14G 122.48(16) . . ? C9G C10G C14G 121.36(16) . . ? C12G C11G C10G 120.00(16) . . ? C12G C11G H11G 120.0 . . ? C10G C11G H11G 120.0 . . ? C13G C12G C11G 118.52(16) . . ? C13G C12G H12G 120.7 . . ? C11G C12G H12G 120.7 . . ? N8G C13G C12G 123.55(16) . . ? N8G C13G H13G 118.2 . . ? C12G C13G H13G 118.2 . . ? C10G C14G H14B 109.5 . . ? C10G C14G H14A 109.5 . . ? H14B C14G H14A 109.5 . . ? C10G C14G H14C 109.5 . . ? H14B C14G H14C 109.5 . . ? H14A C14G H14C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.8(2) . . . . ? C13 C1 C2 C3 171.29(13) . . . . ? C1 C2 C3 C4 1.2(2) . . . . ? C2 C3 C4 C5 0.2(2) . . . . ? C3 C4 C5 C6 -1.0(2) . . . . ? C4 C5 C6 C1 0.3(2) . . . . ? C4 C5 C6 C7 -178.59(13) . . . . ? C2 C1 C6 C5 1.1(2) . . . . ? C13 C1 C6 C5 -173.19(12) . . . . ? C2 C1 C6 C7 -179.81(12) . . . . ? C13 C1 C6 C7 5.94(15) . . . . ? C5 C6 C7 C8 -0.5(2) . . . . ? C1 C6 C7 C8 -179.47(13) . . . . ? C5 C6 C7 C12 178.34(14) . . . . ? C1 C6 C7 C12 -0.66(15) . . . . ? C12 C7 C8 C9 1.2(2) . . . . ? C6 C7 C8 C9 179.90(13) . . . . ? C7 C8 C9 C10 1.5(2) . . . . ? C8 C9 C10 C11 -2.3(2) . . . . ? C9 C10 C11 C12 0.3(2) . . . . ? C10 C11 C12 C7 2.4(2) . . . . ? C10 C11 C12 C13 -174.29(13) . . . . ? C8 C7 C12 C11 -3.2(2) . . . . ? C6 C7 C12 C11 177.82(12) . . . . ? C8 C7 C12 C13 174.07(11) . . . . ? C6 C7 C12 C13 -4.89(15) . . . . ? C11 C12 C13 O13 70.69(17) . . . . ? C7 C12 C13 O13 -106.29(12) . . . . ? C11 C12 C13 C14 -51.40(18) . . . . ? C7 C12 C13 C14 131.62(12) . . . . ? C11 C12 C13 C1 -175.15(13) . . . . ? C7 C12 C13 C1 7.87(13) . . . . ? C2 C1 C13 O13 -66.29(17) . . . . ? C6 C1 C13 O13 107.35(12) . . . . ? C2 C1 C13 C14 55.16(18) . . . . ? C6 C1 C13 C14 -131.20(12) . . . . ? C2 C1 C13 C12 178.04(13) . . . . ? C6 C1 C13 C12 -8.32(13) . . . . ? O13 C13 C14 C15 163.44(11) . . . . ? C12 C13 C14 C15 -73.68(15) . . . . ? C1 C13 C14 C15 42.32(16) . . . . ? O13 C13 C14 C23 -18.69(17) . . . . ? C12 C13 C14 C23 104.19(14) . . . . ? C1 C13 C14 C23 -139.81(13) . . . . ? C23 C14 C15 C16 0.49(19) . . . . ? C13 C14 C15 C16 178.48(12) . . . . ? C14 C15 C16 C21 -0.5(2) . . . . ? C14 C15 C16 C17 -179.85(13) . . . . ? C15 C16 C17 C18 179.88(14) . . . . ? C21 C16 C17 C18 0.6(2) . . . . ? C16 C17 C18 C19 0.1(2) . . . . ? C17 C18 C19 C20 -0.4(3) . . . . ? C18 C19 C20 C21 0.1(3) . . . . ? C15 C16 C21 C22 -0.33(19) . . . . ? C17 C16 C21 C22 179.00(13) . . . . ? C15 C16 C21 C20 179.79(12) . . . . ? C17 C16 C21 C20 -0.9(2) . . . . ? C19 C20 C21 C22 -179.33(15) . . . . ? C19 C20 C21 C16 0.6(2) . . . . ? C16 C21 C22 C23 1.3(2) . . . . ? C20 C21 C22 C23 -178.79(13) . . . . ? C21 C22 C23 C14 -1.4(2) . . . . ? C21 C22 C23 C24 -175.90(13) . . . . ? C15 C14 C23 C22 0.46(19) . . . . ? C13 C14 C23 C22 -177.37(12) . . . . ? C15 C14 C23 C24 174.21(12) . . . . ? C13 C14 C23 C24 -3.6(2) . . . . ? C22 C23 C24 C25 76.89(15) . . . . ? C14 C23 C24 C25 -97.04(16) . . . . ? C22 C23 C24 C33 -95.46(15) . . . . ? C14 C23 C24 C33 90.61(17) . . . . ? C33 C24 C25 C26 -0.9(2) . . . . ? C23 C24 C25 C26 -173.81(12) . . . . ? C24 C25 C26 C31 1.7(2) . . . . ? C24 C25 C26 C27 -178.38(13) . . . . ? C25 C26 C27 C28 178.99(13) . . . . ? C31 C26 C27 C28 -1.1(2) . . . . ? C26 C27 C28 C29 1.4(2) . . . . ? C27 C28 C29 C30 -0.5(2) . . . . ? C28 C29 C30 C31 -0.7(2) . . . . ? C25 C26 C31 C32 -0.60(19) . . . . ? C27 C26 C31 C32 179.49(12) . . . . ? C25 C26 C31 C30 179.78(12) . . . . ? C27 C26 C31 C30 -0.14(19) . . . . ? C29 C30 C31 C26 1.0(2) . . . . ? C29 C30 C31 C32 -178.56(13) . . . . ? C26 C31 C32 C33 -1.30(19) . . . . ? C30 C31 C32 C33 178.30(12) . . . . ? C31 C32 C33 C24 2.09(19) . . . . ? C31 C32 C33 C34 -177.72(11) . . . . ? C25 C24 C33 C32 -0.96(18) . . . . ? C23 C24 C33 C32 171.17(12) . . . . ? C25 C24 C33 C34 178.84(12) . . . . ? C23 C24 C33 C34 -9.0(2) . . . . ? C32 C33 C34 O34 159.11(11) . . . . ? C24 C33 C34 O34 -20.69(17) . . . . ? C32 C33 C34 C35 35.49(15) . . . . ? C24 C33 C34 C35 -144.31(12) . . . . ? C32 C33 C34 C46 -78.09(15) . . . . ? C24 C33 C34 C46 102.11(14) . . . . ? O34 C34 C35 C36 -64.81(17) . . . . ? C46 C34 C35 C36 -178.84(13) . . . . ? C33 C34 C35 C36 60.28(17) . . . . ? O34 C34 C35 C40 113.24(12) . . . . ? C46 C34 C35 C40 -0.79(14) . . . . ? C33 C34 C35 C40 -121.67(12) . . . . ? C40 C35 C36 C37 -0.7(2) . . . . ? C34 C35 C36 C37 177.20(13) . . . . ? C35 C36 C37 C38 -0.1(2) . . . . ? C36 C37 C38 C39 0.5(2) . . . . ? C37 C38 C39 C40 -0.2(2) . . . . ? C38 C39 C40 C35 -0.5(2) . . . . ? C38 C39 C40 C41 -179.41(14) . . . . ? C36 C35 C40 C39 1.0(2) . . . . ? C34 C35 C40 C39 -177.21(12) . . . . ? C36 C35 C40 C41 -179.89(12) . . . . ? C34 C35 C40 C41 1.91(15) . . . . ? C39 C40 C41 C42 -2.7(3) . . . . ? C35 C40 C41 C42 178.32(14) . . . . ? C39 C40 C41 C46 176.65(14) . . . . ? C35 C40 C41 C46 -2.33(15) . . . . ? C46 C41 C42 C43 -1.3(2) . . . . ? C40 C41 C42 C43 177.96(14) . . . . ? C41 C42 C43 C44 0.9(2) . . . . ? C42 C43 C44 C45 -0.3(2) . . . . ? C43 C44 C45 C46 0.0(2) . . . . ? C44 C45 C46 C41 -0.4(2) . . . . ? C44 C45 C46 C34 179.36(13) . . . . ? C42 C41 C46 C45 1.1(2) . . . . ? C40 C41 C46 C45 -178.34(12) . . . . ? C42 C41 C46 C34 -178.73(12) . . . . ? C40 C41 C46 C34 1.83(15) . . . . ? O34 C34 C46 C45 64.30(17) . . . . ? C35 C34 C46 C45 179.52(13) . . . . ? C33 C34 C46 C45 -60.81(18) . . . . ? O34 C34 C46 C41 -115.90(12) . . . . ? C35 C34 C46 C41 -0.68(14) . . . . ? C33 C34 C46 C41 118.99(12) . . . . ? C6G N1G C2G C3G 0.7(2) . . . . ? N1G C2G C3G C4G -1.3(2) . . . . ? N1G C2G C3G C7G 178.18(14) . . . . ? C2G C3G C4G C5G 1.0(2) . . . . ? C7G C3G C4G C5G -178.50(17) . . . . ? C3G C4G C5G C6G -0.2(3) . . . . ? C2G N1G C6G C5G 0.2(2) . . . . ? C4G C5G C6G N1G -0.5(3) . . . . ? C13G N8G C9G C10G -0.4(2) . . . . ? N8G C9G C10G C11G 0.2(2) . . . . ? N8G C9G C10G C14G -179.94(16) . . . . ? C9G C10G C11G C12G 0.3(2) . . . . ? C14G C10G C11G C12G -179.51(17) . . . . ? C10G C11G C12G C13G -0.6(3) . . . . ? C9G N8G C13G C12G 0.0(2) . . . . ? C11G C12G C13G N8G 0.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O34 H34 O13 0.99(2) 1.81(2) 2.7579(14) 161.2(16) . O13 H13 N1G 0.98(2) 1.83(2) 2.8019(16) 173.6(18) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.226 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.040 _database_code_depnum_ccdc_archive 'CCDC 945701' ####################################################################### # # 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_H.4PIC _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C46 H30 O2, C6 H7 N' _chemical_formula_sum 'C52 H37 N O2' _chemical_formula_weight 707.83 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n 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 9.9365(6) _cell_length_b 20.7883(13) _cell_length_c 18.8462(13) _cell_angle_alpha 90.00 _cell_angle_beta 100.617(2) _cell_angle_gamma 90.00 _cell_volume 3826.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.96 _cell_measurement_theta_max 27.14 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.229 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9732 _exptl_absorpt_correction_T_max 0.9876 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker Kappa Duo Apex II Diffractometer' _diffrn_measurement_method '0.5\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 23758 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0575 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 27.14 _reflns_number_total 8459 _reflns_number_gt 5610 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_cell_refinement 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_data_reduction 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0486P)^2^+0.3532P] 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_number_reflns 8459 _refine_ls_number_parameters 505 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0806 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1154 _refine_ls_wR_factor_gt 0.1006 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL p21n in P2(1)/n CELL 0.71073 9.9365 20.7883 18.8462 90.000 100.617 90.000 ZERR 4.0000 0.0006 0.0013 0.0013 0.000 0.002 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 208 148 4 8 MERG 2 FMAP 2 GRID PLAN 1 TEMP -100 SIZE 0.17 0.18 0.37 CONF BOND $H HTAB O34 O13 HTAB O13 N1G OMIT -3 3 9 OMIT 0 1 1 OMIT 0 0 2 L.S. 20 ACTA WGHT 0.048600 0.353200 FVAR 0.14117 O13 4 0.682485 0.225771 0.223881 11.00000 0.02138 0.02581 = 0.03222 -0.00184 0.00081 0.00095 H13 2 0.602026 0.211913 0.191262 11.00000 0.06576 O34 4 0.950525 0.205538 0.226456 11.00000 0.02483 0.02758 = 0.03157 0.00424 0.00919 0.00303 H34 2 0.853335 0.212336 0.213615 11.00000 0.06697 N1G 3 0.442891 0.185045 0.138797 11.00000 0.02720 0.03973 = 0.03501 -0.00044 0.00313 -0.00520 C1 1 0.672469 0.325057 0.156336 11.00000 0.02362 0.02851 = 0.02697 -0.00063 0.00292 -0.00168 C2 1 0.764816 0.319727 0.109930 11.00000 0.02677 0.04112 = 0.03418 0.00163 0.00684 0.00200 AFIX 43 H2 2 0.849620 0.298110 0.124582 11.00000 -1.20000 AFIX 0 C3 1 0.730930 0.346686 0.041335 11.00000 0.03782 0.04877 = 0.02986 -0.00058 0.01072 -0.00384 AFIX 43 H3 2 0.792988 0.343241 0.008733 11.00000 -1.20000 AFIX 0 C4 1 0.607388 0.378526 0.020163 11.00000 0.04029 0.04597 = 0.02550 0.00586 -0.00085 -0.00567 AFIX 43 H4 2 0.585139 0.396037 -0.027108 11.00000 -1.20000 AFIX 0 C5 1 0.515869 0.385143 0.067105 11.00000 0.02983 0.03806 = 0.03221 0.00357 -0.00272 -0.00049 AFIX 43 H5 2 0.432602 0.408117 0.052947 11.00000 -1.20000 AFIX 0 C6 1 0.548438 0.357493 0.135241 11.00000 0.02391 0.02724 = 0.02801 -0.00107 0.00134 -0.00160 C7 1 0.469220 0.352250 0.193793 11.00000 0.02225 0.02785 = 0.02965 -0.00273 0.00207 0.00091 C8 1 0.337571 0.372641 0.197967 11.00000 0.02604 0.04052 = 0.03995 0.00049 0.00024 0.00765 AFIX 43 H8 2 0.285190 0.396746 0.159756 11.00000 -1.20000 AFIX 0 C9 1 0.283844 0.357230 0.258839 11.00000 0.02203 0.04517 = 0.04720 -0.00576 0.00897 0.00622 AFIX 43 H9 2 0.193522 0.370409 0.261848 11.00000 -1.20000 AFIX 0 C10 1 0.360326 0.322893 0.315195 11.00000 0.02974 0.03660 = 0.03810 -0.00392 0.01439 -0.00186 AFIX 43 H10 2 0.322329 0.313201 0.356659 11.00000 -1.20000 AFIX 0 C11 1 0.492520 0.302409 0.311681 11.00000 0.02641 0.02999 = 0.03198 0.00022 0.00509 -0.00021 AFIX 43 H11 2 0.545256 0.278989 0.350371 11.00000 -1.20000 AFIX 0 C12 1 0.545164 0.316965 0.250561 11.00000 0.02044 0.02496 = 0.02956 -0.00238 0.00367 -0.00166 C13 1 0.680223 0.294667 0.230770 11.00000 0.02034 0.02482 = 0.02776 0.00088 0.00407 0.00186 C14 1 0.806363 0.315554 0.285887 11.00000 0.01746 0.02648 = 0.02635 -0.00105 0.00564 0.00147 C15 1 0.850002 0.377965 0.281666 11.00000 0.02476 0.02841 = 0.03264 0.00164 0.00681 0.00419 AFIX 43 H15 2 0.802037 0.404890 0.244740 11.00000 -1.20000 AFIX 0 C16 1 0.963166 0.403921 0.329850 11.00000 0.02393 0.02908 = 0.03258 -0.00543 0.01181 -0.00159 C17 1 1.009651 0.467912 0.323569 11.00000 0.03581 0.02993 = 0.04432 -0.00290 0.01478 -0.00321 AFIX 43 H17 2 0.963344 0.495050 0.286375 11.00000 -1.20000 AFIX 0 C18 1 1.120873 0.490740 0.370827 11.00000 0.04085 0.03589 = 0.05317 -0.01276 0.01973 -0.01424 AFIX 43 H18 2 1.152074 0.533410 0.365850 11.00000 -1.20000 AFIX 0 C19 1 1.188841 0.451358 0.426523 11.00000 0.03759 0.05108 = 0.03811 -0.01526 0.01091 -0.01675 AFIX 43 H19 2 1.265363 0.467796 0.459248 11.00000 -1.20000 AFIX 0 C20 1 1.146374 0.389538 0.434356 11.00000 0.02837 0.04618 = 0.03089 -0.00706 0.00714 -0.00615 AFIX 43 H20 2 1.193074 0.363587 0.472595 11.00000 -1.20000 AFIX 0 C21 1 1.032728 0.364003 0.385537 11.00000 0.02325 0.03396 = 0.02838 -0.00709 0.00977 -0.00267 C22 1 0.985835 0.300201 0.390053 11.00000 0.02259 0.03075 = 0.02562 -0.00001 0.00497 0.00207 AFIX 43 H22 2 1.031302 0.273486 0.427898 11.00000 -1.20000 AFIX 0 C23 1 0.877043 0.274967 0.342000 11.00000 0.02152 0.02674 = 0.02216 -0.00230 0.00749 0.00084 C24 1 0.834850 0.207429 0.358992 11.00000 0.01858 0.02555 = 0.02338 0.00098 0.00000 0.00025 C25 1 0.764045 0.203343 0.415159 11.00000 0.02204 0.02925 = 0.02564 -0.00158 0.00273 0.00197 AFIX 43 H25 2 0.741081 0.242086 0.436865 11.00000 -1.20000 AFIX 0 C26 1 0.723921 0.144312 0.442049 11.00000 0.01799 0.03393 = 0.02594 0.00407 -0.00019 0.00066 C27 1 0.651843 0.140113 0.500567 11.00000 0.02312 0.04592 = 0.02794 0.00196 0.00475 -0.00122 AFIX 43 H27 2 0.624807 0.178328 0.521768 11.00000 -1.20000 AFIX 0 C28 1 0.621323 0.081678 0.526412 11.00000 0.02347 0.05852 = 0.02960 0.00851 0.00380 -0.01001 AFIX 43 H28 2 0.572246 0.079507 0.565100 11.00000 -1.20000 AFIX 0 C29 1 0.661988 0.024473 0.496200 11.00000 0.02808 0.04246 = 0.04068 0.01069 0.00084 -0.01100 AFIX 43 H29 2 0.642513 -0.015946 0.515554 11.00000 -1.20000 AFIX 0 C30 1 0.729251 0.026837 0.439244 11.00000 0.02667 0.03329 = 0.03665 0.00487 0.00057 -0.00468 AFIX 43 H30 2 0.754346 -0.011992 0.418501 11.00000 -1.20000 AFIX 0 C31 1 0.761884 0.086806 0.410862 11.00000 0.01762 0.03090 = 0.02728 0.00379 -0.00244 -0.00329 C32 1 0.834531 0.091439 0.353148 11.00000 0.02065 0.02739 = 0.02829 -0.00057 0.00220 0.00074 AFIX 43 H32 2 0.858750 0.052832 0.331629 11.00000 -1.20000 AFIX 0 C33 1 0.871717 0.149056 0.326742 11.00000 0.01674 0.02759 = 0.02337 0.00035 0.00035 0.00070 C34 1 0.955922 0.146756 0.265972 11.00000 0.01985 0.02410 = 0.02767 0.00082 0.00479 0.00135 C35 1 0.915341 0.090184 0.214751 11.00000 0.02487 0.02900 = 0.02400 0.00068 0.00518 -0.00136 C36 1 0.791363 0.079414 0.169054 11.00000 0.02620 0.03810 = 0.03332 -0.00213 0.00426 -0.00147 AFIX 43 H36 2 0.717198 0.108442 0.168066 11.00000 -1.20000 AFIX 0 C37 1 0.777114 0.025705 0.124824 11.00000 0.03446 0.04701 = 0.03196 -0.00792 0.00278 -0.01069 AFIX 43 H37 2 0.692917 0.017994 0.092878 11.00000 -1.20000 AFIX 0 C38 1 0.885204 -0.016854 0.126972 11.00000 0.05041 0.03893 = 0.04128 -0.01524 0.00820 -0.00639 AFIX 43 H38 2 0.873789 -0.053750 0.096715 11.00000 -1.20000 AFIX 0 C39 1 1.009331 -0.006509 0.172403 11.00000 0.04094 0.03499 = 0.04379 -0.00886 0.00901 0.00565 AFIX 43 H39 2 1.083136 -0.035736 0.173345 11.00000 -1.20000 AFIX 0 C40 1 1.024038 0.047393 0.216607 11.00000 0.02949 0.02828 = 0.02970 -0.00126 0.00672 0.00221 C41 1 1.142397 0.071968 0.268445 11.00000 0.02630 0.03113 = 0.02677 0.00170 0.00742 0.00320 C42 1 1.274142 0.048028 0.289285 11.00000 0.02949 0.04008 = 0.03997 0.00347 0.00811 0.01246 AFIX 43 H42 2 1.298712 0.007558 0.272022 11.00000 -1.20000 AFIX 0 C43 1 1.369349 0.084299 0.335815 11.00000 0.02125 0.05560 = 0.03892 0.00826 0.00195 0.00789 AFIX 43 H43 2 1.459823 0.068421 0.350607 11.00000 -1.20000 AFIX 0 C44 1 1.333882 0.143373 0.360905 11.00000 0.02185 0.05118 = 0.03267 -0.00083 -0.00020 -0.00498 AFIX 43 H44 2 1.400951 0.168146 0.391632 11.00000 -1.20000 AFIX 0 C45 1 1.200979 0.166830 0.341568 11.00000 0.02360 0.03816 = 0.03113 -0.00296 0.00477 -0.00155 AFIX 43 H45 2 1.176214 0.206906 0.359708 11.00000 -1.20000 AFIX 0 C46 1 1.106049 0.130878 0.295660 11.00000 0.01955 0.03065 = 0.02468 0.00119 0.00489 -0.00050 C2G 1 0.330944 0.195091 0.167484 11.00000 0.03689 0.04775 = 0.02855 -0.00478 0.00730 -0.00527 AFIX 43 H2G 2 0.342728 0.211741 0.215173 11.00000 -1.20000 AFIX 0 C3G 1 0.199621 0.182630 0.131705 11.00000 0.02843 0.04459 = 0.03466 0.00092 0.00987 -0.00310 AFIX 43 H3G 2 0.123693 0.190998 0.154455 11.00000 -1.20000 AFIX 0 C4G 1 0.179216 0.157842 0.062406 11.00000 0.02910 0.03983 = 0.03293 0.00281 0.00182 -0.00466 C5G 1 0.294446 0.147444 0.032396 11.00000 0.03805 0.04220 = 0.02714 -0.00493 0.00541 -0.00389 AFIX 43 H5G 2 0.285606 0.130611 -0.015102 11.00000 -1.20000 AFIX 0 C6G 1 0.421902 0.161626 0.071742 11.00000 0.02891 0.03895 = 0.03599 0.00011 0.01070 0.00052 AFIX 43 H6G 2 0.499403 0.154317 0.049895 11.00000 -1.20000 AFIX 0 C7G 1 0.036304 0.142962 0.022795 11.00000 0.03449 0.09783 = 0.05188 -0.00999 -0.00125 -0.01324 AFIX 137 H7B 2 0.013093 0.098410 0.032551 11.00000 -1.50000 H7C 2 0.032014 0.148656 -0.029193 11.00000 -1.50000 H7A 2 -0.028970 0.172160 0.039313 11.00000 -1.50000 HKLF 4 END ; 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 O13 O 0.68249(11) 0.22577(5) 0.22388(6) 0.0270(3) Uani 1 1 d . . . H13 H 0.602(2) 0.2119(10) 0.1913(12) 0.066(7) Uiso 1 1 d . . . O34 O 0.95052(11) 0.20554(5) 0.22646(6) 0.0275(3) Uani 1 1 d . . . H34 H 0.853(2) 0.2123(10) 0.2136(12) 0.067(7) Uiso 1 1 d . . . N1G N 0.44289(14) 0.18505(7) 0.13880(8) 0.0343(3) Uani 1 1 d . . . C1 C 0.67247(16) 0.32506(8) 0.15634(9) 0.0266(4) Uani 1 1 d . . . C2 C 0.76482(17) 0.31973(9) 0.10993(10) 0.0339(4) Uani 1 1 d . . . H2 H 0.8496 0.2981 0.1246 0.041 Uiso 1 1 calc R . . C3 C 0.73093(18) 0.34669(9) 0.04133(10) 0.0382(4) Uani 1 1 d . . . H3 H 0.7930 0.3432 0.0087 0.046 Uiso 1 1 calc R . . C4 C 0.60739(18) 0.37853(9) 0.02016(10) 0.0381(4) Uani 1 1 d . . . H4 H 0.5851 0.3960 -0.0271 0.046 Uiso 1 1 calc R . . C5 C 0.51587(17) 0.38514(8) 0.06710(9) 0.0344(4) Uani 1 1 d . . . H5 H 0.4326 0.4081 0.0529 0.041 Uiso 1 1 calc R . . C6 C 0.54844(16) 0.35749(8) 0.13524(9) 0.0268(4) Uani 1 1 d . . . C7 C 0.46922(16) 0.35225(8) 0.19379(9) 0.0269(4) Uani 1 1 d . . . C8 C 0.33757(17) 0.37264(9) 0.19797(10) 0.0362(4) Uani 1 1 d . . . H8 H 0.2852 0.3967 0.1598 0.043 Uiso 1 1 calc R . . C9 C 0.28384(17) 0.35723(9) 0.25884(10) 0.0378(4) Uani 1 1 d . . . H9 H 0.1935 0.3704 0.2618 0.045 Uiso 1 1 calc R . . C10 C 0.36033(17) 0.32289(8) 0.31519(10) 0.0338(4) Uani 1 1 d . . . H10 H 0.3223 0.3132 0.3567 0.041 Uiso 1 1 calc R . . C11 C 0.49252(16) 0.30241(8) 0.31168(9) 0.0295(4) Uani 1 1 d . . . H11 H 0.5453 0.2790 0.3504 0.035 Uiso 1 1 calc R . . C12 C 0.54516(15) 0.31697(7) 0.25056(9) 0.0251(3) Uani 1 1 d . . . C13 C 0.68022(15) 0.29467(7) 0.23077(9) 0.0244(3) Uani 1 1 d . . . C14 C 0.80636(15) 0.31555(7) 0.28589(8) 0.0232(3) Uani 1 1 d . . . C15 C 0.85000(16) 0.37797(8) 0.28167(9) 0.0284(4) Uani 1 1 d . . . H15 H 0.8020 0.4049 0.2447 0.034 Uiso 1 1 calc R . . C16 C 0.96317(16) 0.40392(8) 0.32985(9) 0.0277(4) Uani 1 1 d . . . C17 C 1.00965(18) 0.46791(8) 0.32357(10) 0.0357(4) Uani 1 1 d . . . H17 H 0.9633 0.4951 0.2864 0.043 Uiso 1 1 calc R . . C18 C 1.12087(19) 0.49074(9) 0.37083(11) 0.0419(5) Uani 1 1 d . . . H18 H 1.1521 0.5334 0.3658 0.050 Uiso 1 1 calc R . . C19 C 1.18884(19) 0.45136(10) 0.42652(10) 0.0418(5) Uani 1 1 d . . . H19 H 1.2654 0.4678 0.4592 0.050 Uiso 1 1 calc R . . C20 C 1.14637(17) 0.38954(9) 0.43436(10) 0.0349(4) Uani 1 1 d . . . H20 H 1.1931 0.3636 0.4726 0.042 Uiso 1 1 calc R . . C21 C 1.03273(16) 0.36400(8) 0.38554(9) 0.0279(4) Uani 1 1 d . . . C22 C 0.98583(15) 0.30020(8) 0.39005(9) 0.0263(4) Uani 1 1 d . . . H22 H 1.0313 0.2735 0.4279 0.032 Uiso 1 1 calc R . . C23 C 0.87704(15) 0.27497(7) 0.34200(8) 0.0230(3) Uani 1 1 d . . . C24 C 0.83485(15) 0.20743(7) 0.35899(8) 0.0230(3) Uani 1 1 d . . . C25 C 0.76405(15) 0.20334(8) 0.41516(8) 0.0259(4) Uani 1 1 d . . . H25 H 0.7411 0.2421 0.4369 0.031 Uiso 1 1 calc R . . C26 C 0.72392(15) 0.14431(8) 0.44205(9) 0.0265(4) Uani 1 1 d . . . C27 C 0.65184(16) 0.14011(9) 0.50057(9) 0.0323(4) Uani 1 1 d . . . H27 H 0.6248 0.1783 0.5218 0.039 Uiso 1 1 calc R . . C28 C 0.62132(16) 0.08168(9) 0.52641(10) 0.0373(4) Uani 1 1 d . . . H28 H 0.5722 0.0795 0.5651 0.045 Uiso 1 1 calc R . . C29 C 0.66199(17) 0.02447(9) 0.49620(10) 0.0378(4) Uani 1 1 d . . . H29 H 0.6425 -0.0159 0.5156 0.045 Uiso 1 1 calc R . . C30 C 0.72925(16) 0.02684(8) 0.43924(10) 0.0329(4) Uani 1 1 d . . . H30 H 0.7543 -0.0120 0.4185 0.039 Uiso 1 1 calc R . . C31 C 0.76188(15) 0.08681(8) 0.41086(9) 0.0261(4) Uani 1 1 d . . . C32 C 0.83453(15) 0.09144(8) 0.35315(9) 0.0257(4) Uani 1 1 d . . . H32 H 0.8587 0.0528 0.3316 0.031 Uiso 1 1 calc R . . C33 C 0.87172(14) 0.14906(7) 0.32674(8) 0.0230(3) Uani 1 1 d . . . C34 C 0.95592(15) 0.14676(7) 0.26597(9) 0.0238(3) Uani 1 1 d . . . C35 C 0.91534(15) 0.09018(8) 0.21475(9) 0.0259(4) Uani 1 1 d . . . C36 C 0.79136(17) 0.07941(8) 0.16905(9) 0.0327(4) Uani 1 1 d . . . H36 H 0.7172 0.1084 0.1681 0.039 Uiso 1 1 calc R . . C37 C 0.77711(19) 0.02570(9) 0.12482(10) 0.0382(4) Uani 1 1 d . . . H37 H 0.6929 0.0180 0.0929 0.046 Uiso 1 1 calc R . . C38 C 0.8852(2) -0.01685(9) 0.12697(11) 0.0436(5) Uani 1 1 d . . . H38 H 0.8738 -0.0537 0.0967 0.052 Uiso 1 1 calc R . . C39 C 1.00933(19) -0.00651(9) 0.17240(10) 0.0398(4) Uani 1 1 d . . . H39 H 1.0831 -0.0357 0.1733 0.048 Uiso 1 1 calc R . . C40 C 1.02404(16) 0.04739(8) 0.21661(9) 0.0290(4) Uani 1 1 d . . . C41 C 1.14240(16) 0.07197(8) 0.26845(9) 0.0277(4) Uani 1 1 d . . . C42 C 1.27414(17) 0.04803(9) 0.28929(10) 0.0363(4) Uani 1 1 d . . . H42 H 1.2987 0.0076 0.2720 0.044 Uiso 1 1 calc R . . C43 C 1.36935(17) 0.08430(9) 0.33582(10) 0.0390(5) Uani 1 1 d . . . H43 H 1.4598 0.0684 0.3506 0.047 Uiso 1 1 calc R . . C44 C 1.33388(17) 0.14337(9) 0.36090(10) 0.0359(4) Uani 1 1 d . . . H44 H 1.4010 0.1681 0.3916 0.043 Uiso 1 1 calc R . . C45 C 1.20098(16) 0.16683(8) 0.34157(9) 0.0310(4) Uani 1 1 d . . . H45 H 1.1762 0.2069 0.3597 0.037 Uiso 1 1 calc R . . C46 C 1.10605(15) 0.13088(8) 0.29566(8) 0.0249(3) Uani 1 1 d . . . C2G C 0.33094(18) 0.19509(9) 0.16748(10) 0.0376(4) Uani 1 1 d . . . H2G H 0.3427 0.2117 0.2152 0.045 Uiso 1 1 calc R . . C3G C 0.19962(17) 0.18263(9) 0.13170(10) 0.0354(4) Uani 1 1 d . . . H3G H 0.1237 0.1910 0.1545 0.042 Uiso 1 1 calc R . . C4G C 0.17922(17) 0.15784(9) 0.06241(10) 0.0344(4) Uani 1 1 d . . . C5G C 0.29445(18) 0.14744(9) 0.03240(10) 0.0359(4) Uani 1 1 d . . . H5G H 0.2856 0.1306 -0.0151 0.043 Uiso 1 1 calc R . . C6G C 0.42190(17) 0.16163(8) 0.07174(10) 0.0340(4) Uani 1 1 d . . . H6G H 0.4994 0.1543 0.0499 0.041 Uiso 1 1 calc R . . C7G C 0.0363(2) 0.14296(13) 0.02280(12) 0.0626(7) Uani 1 1 d . . . H7B H 0.0131 0.0984 0.0326 0.094 Uiso 1 1 calc R . . H7C H 0.0320 0.1487 -0.0292 0.094 Uiso 1 1 calc R . . H7A H -0.0290 0.1722 0.0393 0.094 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 O13 0.0214(6) 0.0258(6) 0.0322(6) -0.0018(5) 0.0008(5) 0.0010(5) O34 0.0248(6) 0.0276(6) 0.0316(6) 0.0042(5) 0.0092(5) 0.0030(5) N1G 0.0272(7) 0.0397(9) 0.0350(9) -0.0004(7) 0.0031(6) -0.0052(7) C1 0.0236(8) 0.0285(9) 0.0270(9) -0.0006(7) 0.0029(7) -0.0017(7) C2 0.0268(9) 0.0411(10) 0.0342(10) 0.0016(8) 0.0068(7) 0.0020(8) C3 0.0378(10) 0.0488(11) 0.0299(10) -0.0006(9) 0.0107(8) -0.0038(9) C4 0.0403(10) 0.0460(11) 0.0255(9) 0.0059(9) -0.0008(8) -0.0057(9) C5 0.0298(9) 0.0381(10) 0.0322(10) 0.0036(8) -0.0027(7) -0.0005(8) C6 0.0239(8) 0.0272(8) 0.0280(9) -0.0011(7) 0.0013(7) -0.0016(7) C7 0.0223(8) 0.0278(8) 0.0296(9) -0.0027(7) 0.0021(7) 0.0009(7) C8 0.0260(9) 0.0405(10) 0.0399(11) 0.0005(9) 0.0002(8) 0.0076(8) C9 0.0220(8) 0.0452(11) 0.0472(11) -0.0058(9) 0.0090(8) 0.0062(8) C10 0.0297(9) 0.0366(10) 0.0381(10) -0.0039(8) 0.0144(8) -0.0019(8) C11 0.0264(8) 0.0300(9) 0.0320(9) 0.0002(8) 0.0051(7) -0.0002(7) C12 0.0204(8) 0.0250(8) 0.0296(9) -0.0024(7) 0.0037(6) -0.0017(7) C13 0.0203(7) 0.0248(8) 0.0278(9) 0.0009(7) 0.0041(6) 0.0019(6) C14 0.0175(7) 0.0265(8) 0.0264(8) -0.0011(7) 0.0056(6) 0.0015(6) C15 0.0248(8) 0.0284(9) 0.0326(9) 0.0016(7) 0.0068(7) 0.0042(7) C16 0.0239(8) 0.0291(9) 0.0326(9) -0.0054(8) 0.0118(7) -0.0016(7) C17 0.0358(10) 0.0299(9) 0.0443(11) -0.0029(8) 0.0148(8) -0.0032(8) C18 0.0409(11) 0.0359(10) 0.0532(12) -0.0128(10) 0.0197(9) -0.0142(9) C19 0.0376(10) 0.0511(12) 0.0381(11) -0.0153(10) 0.0109(8) -0.0168(9) C20 0.0284(9) 0.0462(11) 0.0309(9) -0.0071(9) 0.0071(7) -0.0061(8) C21 0.0233(8) 0.0340(9) 0.0284(9) -0.0071(8) 0.0098(7) -0.0027(7) C22 0.0226(8) 0.0307(9) 0.0256(9) 0.0000(7) 0.0050(6) 0.0021(7) C23 0.0215(8) 0.0267(8) 0.0222(8) -0.0023(7) 0.0075(6) 0.0008(7) C24 0.0186(7) 0.0255(8) 0.0234(8) 0.0010(7) 0.0000(6) 0.0003(6) C25 0.0220(8) 0.0292(9) 0.0256(9) -0.0016(7) 0.0027(6) 0.0020(7) C26 0.0180(8) 0.0339(9) 0.0259(8) 0.0041(7) -0.0002(6) 0.0007(7) C27 0.0231(8) 0.0459(11) 0.0279(9) 0.0020(8) 0.0048(7) -0.0012(8) C28 0.0235(8) 0.0585(12) 0.0296(10) 0.0085(9) 0.0038(7) -0.0100(8) C29 0.0281(9) 0.0425(11) 0.0407(11) 0.0107(9) 0.0008(8) -0.0110(8) C30 0.0267(9) 0.0333(9) 0.0367(10) 0.0049(8) 0.0006(7) -0.0047(7) C31 0.0176(7) 0.0309(9) 0.0273(9) 0.0038(7) -0.0024(6) -0.0033(7) C32 0.0206(8) 0.0274(9) 0.0283(9) -0.0006(7) 0.0022(6) 0.0007(7) C33 0.0167(7) 0.0276(8) 0.0234(8) 0.0003(7) 0.0004(6) 0.0007(6) C34 0.0198(8) 0.0241(8) 0.0277(8) 0.0008(7) 0.0048(6) 0.0013(6) C35 0.0249(8) 0.0290(9) 0.0240(8) 0.0007(7) 0.0052(7) -0.0014(7) C36 0.0262(9) 0.0381(10) 0.0333(10) -0.0021(8) 0.0043(7) -0.0015(8) C37 0.0345(10) 0.0470(11) 0.0320(10) -0.0079(9) 0.0028(8) -0.0107(9) C38 0.0504(12) 0.0389(11) 0.0413(11) -0.0152(9) 0.0082(9) -0.0064(9) C39 0.0409(10) 0.0350(10) 0.0438(11) -0.0089(9) 0.0090(9) 0.0057(8) C40 0.0295(8) 0.0283(9) 0.0297(9) -0.0013(7) 0.0067(7) 0.0022(7) C41 0.0263(8) 0.0311(9) 0.0268(9) 0.0017(7) 0.0074(7) 0.0032(7) C42 0.0295(9) 0.0401(10) 0.0400(10) 0.0035(9) 0.0081(8) 0.0125(8) C43 0.0213(9) 0.0556(12) 0.0389(11) 0.0083(9) 0.0019(8) 0.0079(8) C44 0.0219(8) 0.0512(11) 0.0327(10) -0.0008(9) -0.0002(7) -0.0050(8) C45 0.0236(8) 0.0382(10) 0.0311(9) -0.0030(8) 0.0048(7) -0.0015(7) C46 0.0196(8) 0.0306(9) 0.0247(8) 0.0012(7) 0.0049(6) -0.0005(7) C2G 0.0369(10) 0.0477(11) 0.0285(10) -0.0048(9) 0.0073(8) -0.0053(9) C3G 0.0284(9) 0.0446(11) 0.0347(10) 0.0009(9) 0.0099(8) -0.0031(8) C4G 0.0291(9) 0.0398(10) 0.0329(10) 0.0028(8) 0.0018(7) -0.0047(8) C5G 0.0380(10) 0.0422(10) 0.0271(9) -0.0049(8) 0.0054(8) -0.0039(8) C6G 0.0289(9) 0.0389(10) 0.0360(10) 0.0001(8) 0.0107(8) 0.0005(8) C7G 0.0345(11) 0.0978(19) 0.0519(14) -0.0100(13) -0.0013(10) -0.0132(12) _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 O13 C13 1.4386(19) . ? O13 H13 0.96(2) . ? O34 C34 1.4269(18) . ? O34 H34 0.96(2) . ? N1G C6G 1.334(2) . ? N1G C2G 1.340(2) . ? C1 C2 1.384(2) . ? C1 C6 1.397(2) . ? C1 C13 1.527(2) . ? C2 C3 1.392(2) . ? C2 H2 0.9500 . ? C3 C4 1.387(2) . ? C3 H3 0.9500 . ? C4 C5 1.387(3) . ? C4 H4 0.9500 . ? C5 C6 1.390(2) . ? C5 H5 0.9500 . ? C6 C7 1.473(2) . ? C7 C8 1.391(2) . ? C7 C12 1.398(2) . ? C8 C9 1.389(3) . ? C8 H8 0.9500 . ? C9 C10 1.385(3) . ? C9 H9 0.9500 . ? C10 C11 1.394(2) . ? C10 H10 0.9500 . ? C11 C12 1.383(2) . ? C11 H11 0.9500 . ? C12 C13 1.530(2) . ? C13 C14 1.536(2) . ? C14 C15 1.375(2) . ? C14 C23 1.432(2) . ? C15 C16 1.416(2) . ? C15 H15 0.9500 . ? C16 C21 1.414(2) . ? C16 C17 1.420(2) . ? C17 C18 1.370(3) . ? C17 H17 0.9500 . ? C18 C19 1.402(3) . ? C18 H18 0.9500 . ? C19 C20 1.369(3) . ? C19 H19 0.9500 . ? C20 C21 1.422(2) . ? C20 H20 0.9500 . ? C21 C22 1.414(2) . ? C22 C23 1.380(2) . ? C22 H22 0.9500 . ? C23 C24 1.516(2) . ? C24 C25 1.377(2) . ? C24 C33 1.435(2) . ? C25 C26 1.413(2) . ? C25 H25 0.9500 . ? C26 C31 1.414(2) . ? C26 C27 1.424(2) . ? C27 C28 1.364(2) . ? C27 H27 0.9500 . ? C28 C29 1.409(3) . ? C28 H28 0.9500 . ? C29 C30 1.366(2) . ? C29 H29 0.9500 . ? C30 C31 1.418(2) . ? C30 H30 0.9500 . ? C31 C32 1.415(2) . ? C32 C33 1.374(2) . ? C32 H32 0.9500 . ? C33 C34 1.539(2) . ? C34 C35 1.528(2) . ? C34 C46 1.530(2) . ? C35 C36 1.385(2) . ? C35 C40 1.395(2) . ? C36 C37 1.385(2) . ? C36 H36 0.9500 . ? C37 C38 1.386(3) . ? C37 H37 0.9500 . ? C38 C39 1.383(3) . ? C38 H38 0.9500 . ? C39 C40 1.388(2) . ? C39 H39 0.9500 . ? C40 C41 1.475(2) . ? C41 C42 1.388(2) . ? C41 C46 1.401(2) . ? C42 C43 1.388(3) . ? C42 H42 0.9500 . ? C43 C44 1.385(3) . ? C43 H43 0.9500 . ? C44 C45 1.392(2) . ? C44 H44 0.9500 . ? C45 C46 1.377(2) . ? C45 H45 0.9500 . ? C2G C3G 1.379(2) . ? C2G H2G 0.9500 . ? C3G C4G 1.384(2) . ? C3G H3G 0.9500 . ? C4G C5G 1.384(2) . ? C4G C7G 1.510(2) . ? C5G C6G 1.376(2) . ? C5G H5G 0.9500 . ? C6G H6G 0.9500 . ? C7G H7B 0.9800 . ? C7G H7C 0.9800 . ? C7G H7A 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O13 H13 109.4(13) . . ? C34 O34 H34 101.3(13) . . ? C6G N1G C2G 116.27(15) . . ? C2 C1 C6 120.78(15) . . ? C2 C1 C13 128.33(15) . . ? C6 C1 C13 110.71(14) . . ? C1 C2 C3 118.66(16) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 120.60(17) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 120.88(16) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C4 C5 C6 118.67(16) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C5 C6 C1 120.38(16) . . ? C5 C6 C7 131.10(15) . . ? C1 C6 C7 108.44(14) . . ? C8 C7 C12 119.82(16) . . ? C8 C7 C6 131.13(16) . . ? C12 C7 C6 108.94(14) . . ? C9 C8 C7 119.01(16) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C10 C9 C8 120.81(16) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 120.65(17) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C12 C11 C10 118.48(16) . . ? C12 C11 H11 120.8 . . ? C10 C11 H11 120.8 . . ? C11 C12 C7 121.22(15) . . ? C11 C12 C13 128.32(14) . . ? C7 C12 C13 110.28(14) . . ? O13 C13 C1 109.14(13) . . ? O13 C13 C12 110.65(12) . . ? C1 C13 C12 101.57(12) . . ? O13 C13 C14 108.55(12) . . ? C1 C13 C14 113.64(13) . . ? C12 C13 C14 113.13(13) . . ? C15 C14 C23 118.81(14) . . ? C15 C14 C13 117.03(14) . . ? C23 C14 C13 124.13(13) . . ? C14 C15 C16 122.97(15) . . ? C14 C15 H15 118.5 . . ? C16 C15 H15 118.5 . . ? C21 C16 C15 118.31(15) . . ? C21 C16 C17 119.30(15) . . ? C15 C16 C17 122.39(16) . . ? C18 C17 C16 120.40(18) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C17 C18 C19 120.26(17) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C20 C19 C18 120.87(17) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C19 C20 C21 120.31(18) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C22 C21 C16 118.28(14) . . ? C22 C21 C20 122.87(16) . . ? C16 C21 C20 118.85(15) . . ? C23 C22 C21 122.98(15) . . ? C23 C22 H22 118.5 . . ? C21 C22 H22 118.5 . . ? C22 C23 C14 118.63(14) . . ? C22 C23 C24 115.29(14) . . ? C14 C23 C24 125.77(13) . . ? C25 C24 C33 118.68(14) . . ? C25 C24 C23 114.81(14) . . ? C33 C24 C23 126.27(14) . . ? C24 C25 C26 123.17(15) . . ? C24 C25 H25 118.4 . . ? C26 C25 H25 118.4 . . ? C25 C26 C31 118.09(15) . . ? C25 C26 C27 123.12(16) . . ? C31 C26 C27 118.75(15) . . ? C28 C27 C26 120.53(17) . . ? C28 C27 H27 119.7 . . ? C26 C27 H27 119.7 . . ? C27 C28 C29 120.54(17) . . ? C27 C28 H28 119.7 . . ? C29 C28 H28 119.7 . . ? C30 C29 C28 120.35(17) . . ? C30 C29 H29 119.8 . . ? C28 C29 H29 119.8 . . ? C29 C30 C31 120.48(17) . . ? C29 C30 H30 119.8 . . ? C31 C30 H30 119.8 . . ? C26 C31 C32 118.36(15) . . ? C26 C31 C30 119.32(16) . . ? C32 C31 C30 122.31(16) . . ? C33 C32 C31 123.17(15) . . ? C33 C32 H32 118.4 . . ? C31 C32 H32 118.4 . . ? C32 C33 C24 118.51(15) . . ? C32 C33 C34 117.52(14) . . ? C24 C33 C34 123.92(14) . . ? O34 C34 C35 110.44(12) . . ? O34 C34 C46 108.42(12) . . ? C35 C34 C46 101.02(12) . . ? O34 C34 C33 112.87(12) . . ? C35 C34 C33 112.20(12) . . ? C46 C34 C33 111.22(13) . . ? C36 C35 C40 120.56(15) . . ? C36 C35 C34 128.19(14) . . ? C40 C35 C34 111.23(13) . . ? C37 C36 C35 119.02(16) . . ? C37 C36 H36 120.5 . . ? C35 C36 H36 120.5 . . ? C36 C37 C38 120.28(16) . . ? C36 C37 H37 119.9 . . ? C38 C37 H37 119.9 . . ? C39 C38 C37 121.12(17) . . ? C39 C38 H38 119.4 . . ? C37 C38 H38 119.4 . . ? C38 C39 C40 118.72(17) . . ? C38 C39 H39 120.6 . . ? C40 C39 H39 120.6 . . ? C39 C40 C35 120.30(15) . . ? C39 C40 C41 131.32(15) . . ? C35 C40 C41 108.36(14) . . ? C42 C41 C46 120.22(16) . . ? C42 C41 C40 131.20(16) . . ? C46 C41 C40 108.51(14) . . ? C41 C42 C43 118.78(17) . . ? C41 C42 H42 120.6 . . ? C43 C42 H42 120.6 . . ? C44 C43 C42 120.72(16) . . ? C44 C43 H43 119.6 . . ? C42 C43 H43 119.6 . . ? C43 C44 C45 120.68(16) . . ? C43 C44 H44 119.7 . . ? C45 C44 H44 119.7 . . ? C46 C45 C44 118.78(16) . . ? C46 C45 H45 120.6 . . ? C44 C45 H45 120.6 . . ? C45 C46 C41 120.77(14) . . ? C45 C46 C34 128.44(15) . . ? C41 C46 C34 110.77(13) . . ? N1G C2G C3G 123.70(17) . . ? N1G C2G H2G 118.2 . . ? C3G C2G H2G 118.2 . . ? C2G C3G C4G 119.51(16) . . ? C2G C3G H3G 120.2 . . ? C4G C3G H3G 120.2 . . ? C3G C4G C5G 117.09(16) . . ? C3G C4G C7G 120.26(17) . . ? C5G C4G C7G 122.65(17) . . ? C6G C5G C4G 119.65(16) . . ? C6G C5G H5G 120.2 . . ? C4G C5G H5G 120.2 . . ? N1G C6G C5G 123.79(16) . . ? N1G C6G H6G 118.1 . . ? C5G C6G H6G 118.1 . . ? C4G C7G H7B 109.5 . . ? C4G C7G H7C 109.5 . . ? H7B C7G H7C 109.5 . . ? C4G C7G H7A 109.5 . . ? H7B C7G H7A 109.5 . . ? H7C C7G H7A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.8(3) . . . . ? C13 C1 C2 C3 173.94(16) . . . . ? C1 C2 C3 C4 0.3(3) . . . . ? C2 C3 C4 C5 1.0(3) . . . . ? C3 C4 C5 C6 -1.9(3) . . . . ? C4 C5 C6 C1 1.5(3) . . . . ? C4 C5 C6 C7 -174.89(17) . . . . ? C2 C1 C6 C5 -0.1(2) . . . . ? C13 C1 C6 C5 -175.72(15) . . . . ? C2 C1 C6 C7 176.99(15) . . . . ? C13 C1 C6 C7 1.41(18) . . . . ? C5 C6 C7 C8 1.0(3) . . . . ? C1 C6 C7 C8 -175.72(17) . . . . ? C5 C6 C7 C12 177.00(17) . . . . ? C1 C6 C7 C12 0.29(18) . . . . ? C12 C7 C8 C9 -0.2(3) . . . . ? C6 C7 C8 C9 175.47(17) . . . . ? C7 C8 C9 C10 0.9(3) . . . . ? C8 C9 C10 C11 -0.7(3) . . . . ? C9 C10 C11 C12 -0.2(3) . . . . ? C10 C11 C12 C7 1.0(2) . . . . ? C10 C11 C12 C13 -173.58(15) . . . . ? C8 C7 C12 C11 -0.8(2) . . . . ? C6 C7 C12 C11 -177.33(15) . . . . ? C8 C7 C12 C13 174.67(15) . . . . ? C6 C7 C12 C13 -1.87(18) . . . . ? C2 C1 C13 O13 -60.6(2) . . . . ? C6 C1 C13 O13 114.51(14) . . . . ? C2 C1 C13 C12 -177.53(16) . . . . ? C6 C1 C13 C12 -2.37(17) . . . . ? C2 C1 C13 C14 60.7(2) . . . . ? C6 C1 C13 C14 -124.19(14) . . . . ? C11 C12 C13 O13 61.8(2) . . . . ? C7 C12 C13 O13 -113.23(14) . . . . ? C11 C12 C13 C1 177.59(16) . . . . ? C7 C12 C13 C1 2.54(16) . . . . ? C11 C12 C13 C14 -60.2(2) . . . . ? C7 C12 C13 C14 124.72(15) . . . . ? O13 C13 C14 C15 157.34(14) . . . . ? C1 C13 C14 C15 35.71(19) . . . . ? C12 C13 C14 C15 -79.44(17) . . . . ? O13 C13 C14 C23 -24.8(2) . . . . ? C1 C13 C14 C23 -146.45(15) . . . . ? C12 C13 C14 C23 98.39(17) . . . . ? C23 C14 C15 C16 0.8(2) . . . . ? C13 C14 C15 C16 178.78(14) . . . . ? C14 C15 C16 C21 -1.1(2) . . . . ? C14 C15 C16 C17 178.10(15) . . . . ? C21 C16 C17 C18 0.1(2) . . . . ? C15 C16 C17 C18 -179.07(16) . . . . ? C16 C17 C18 C19 -0.9(3) . . . . ? C17 C18 C19 C20 0.5(3) . . . . ? C18 C19 C20 C21 0.5(3) . . . . ? C15 C16 C21 C22 0.2(2) . . . . ? C17 C16 C21 C22 -179.07(15) . . . . ? C15 C16 C21 C20 -179.88(14) . . . . ? C17 C16 C21 C20 0.9(2) . . . . ? C19 C20 C21 C22 178.75(16) . . . . ? C19 C20 C21 C16 -1.2(2) . . . . ? C16 C21 C22 C23 1.1(2) . . . . ? C20 C21 C22 C23 -178.86(15) . . . . ? C21 C22 C23 C14 -1.4(2) . . . . ? C21 C22 C23 C24 -175.44(14) . . . . ? C15 C14 C23 C22 0.4(2) . . . . ? C13 C14 C23 C22 -177.37(14) . . . . ? C15 C14 C23 C24 173.78(14) . . . . ? C13 C14 C23 C24 -4.0(2) . . . . ? C22 C23 C24 C25 75.11(17) . . . . ? C14 C23 C24 C25 -98.44(18) . . . . ? C22 C23 C24 C33 -99.21(18) . . . . ? C14 C23 C24 C33 87.2(2) . . . . ? C33 C24 C25 C26 -1.0(2) . . . . ? C23 C24 C25 C26 -175.75(14) . . . . ? C24 C25 C26 C31 1.8(2) . . . . ? C24 C25 C26 C27 179.39(14) . . . . ? C25 C26 C27 C28 -176.94(15) . . . . ? C31 C26 C27 C28 0.6(2) . . . . ? C26 C27 C28 C29 0.7(2) . . . . ? C27 C28 C29 C30 -1.8(3) . . . . ? C28 C29 C30 C31 1.5(3) . . . . ? C25 C26 C31 C32 -1.7(2) . . . . ? C27 C26 C31 C32 -179.46(13) . . . . ? C25 C26 C31 C30 176.74(13) . . . . ? C27 C26 C31 C30 -1.0(2) . . . . ? C29 C30 C31 C26 -0.1(2) . . . . ? C29 C30 C31 C32 178.34(15) . . . . ? C26 C31 C32 C33 1.0(2) . . . . ? C30 C31 C32 C33 -177.41(15) . . . . ? C31 C32 C33 C24 -0.2(2) . . . . ? C31 C32 C33 C34 177.40(13) . . . . ? C25 C24 C33 C32 0.2(2) . . . . ? C23 C24 C33 C32 174.27(14) . . . . ? C25 C24 C33 C34 -177.29(13) . . . . ? C23 C24 C33 C34 -3.2(2) . . . . ? C32 C33 C34 O34 160.36(13) . . . . ? C24 C33 C34 O34 -22.2(2) . . . . ? C32 C33 C34 C35 34.80(18) . . . . ? C24 C33 C34 C35 -147.74(14) . . . . ? C32 C33 C34 C46 -77.52(17) . . . . ? C24 C33 C34 C46 99.94(16) . . . . ? O34 C34 C35 C36 -62.0(2) . . . . ? C46 C34 C35 C36 -176.60(16) . . . . ? C33 C34 C35 C36 64.9(2) . . . . ? O34 C34 C35 C40 116.32(14) . . . . ? C46 C34 C35 C40 1.73(17) . . . . ? C33 C34 C35 C40 -116.80(15) . . . . ? C40 C35 C36 C37 -0.4(3) . . . . ? C34 C35 C36 C37 177.78(16) . . . . ? C35 C36 C37 C38 0.6(3) . . . . ? C36 C37 C38 C39 -0.6(3) . . . . ? C37 C38 C39 C40 0.4(3) . . . . ? C38 C39 C40 C35 -0.2(3) . . . . ? C38 C39 C40 C41 -178.21(18) . . . . ? C36 C35 C40 C39 0.2(3) . . . . ? C34 C35 C40 C39 -178.27(16) . . . . ? C36 C35 C40 C41 178.63(15) . . . . ? C34 C35 C40 C41 0.15(19) . . . . ? C39 C40 C41 C42 -1.0(3) . . . . ? C35 C40 C41 C42 -179.21(18) . . . . ? C39 C40 C41 C46 175.98(18) . . . . ? C35 C40 C41 C46 -2.21(19) . . . . ? C46 C41 C42 C43 -1.7(3) . . . . ? C40 C41 C42 C43 175.00(17) . . . . ? C41 C42 C43 C44 -0.2(3) . . . . ? C42 C43 C44 C45 1.8(3) . . . . ? C43 C44 C45 C46 -1.5(3) . . . . ? C44 C45 C46 C41 -0.4(2) . . . . ? C44 C45 C46 C34 -178.95(16) . . . . ? C42 C41 C46 C45 2.0(3) . . . . ? C40 C41 C46 C45 -175.37(15) . . . . ? C42 C41 C46 C34 -179.22(15) . . . . ? C40 C41 C46 C34 3.40(19) . . . . ? O34 C34 C46 C45 59.4(2) . . . . ? C35 C34 C46 C45 175.54(16) . . . . ? C33 C34 C46 C45 -65.2(2) . . . . ? O34 C34 C46 C41 -119.22(14) . . . . ? C35 C34 C46 C41 -3.12(17) . . . . ? C33 C34 C46 C41 116.12(15) . . . . ? C6G N1G C2G C3G 0.0(3) . . . . ? N1G C2G C3G C4G 0.5(3) . . . . ? C2G C3G C4G C5G -0.6(3) . . . . ? C2G C3G C4G C7G 179.09(19) . . . . ? C3G C4G C5G C6G 0.2(3) . . . . ? C7G C4G C5G C6G -179.50(19) . . . . ? C2G N1G C6G C5G -0.5(3) . . . . ? C4G C5G C6G N1G 0.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O34 H34 O13 0.96(2) 1.77(2) 2.6880(15) 159(2) . O13 H13 N1G 0.96(2) 1.79(2) 2.7476(17) 174(2) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.14 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.216 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 945702' ####################################################################### # # 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_H.2PIC/3PIC(0.32:0.68)-IV _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C46 H30 O2, C6 H7 N' _chemical_formula_sum 'C52 H37 N O2' _chemical_formula_weight 707.83 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n 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 9.8747(8) _cell_length_b 20.9315(16) _cell_length_c 18.7773(14) _cell_angle_alpha 90.00 _cell_angle_beta 99.001(2) _cell_angle_gamma 90.00 _cell_volume 3833.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 29477 _cell_measurement_theta_min 1.95 _cell_measurement_theta_max 27.13 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9811 _exptl_absorpt_correction_T_max 0.9956 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker Kappa Duo Apex II Diffractometer' _diffrn_measurement_method '0.5\% \f scans and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 29477 _diffrn_reflns_av_R_equivalents 0.0511 _diffrn_reflns_av_sigmaI/netI 0.0589 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 27.13 _reflns_number_total 8466 _reflns_number_gt 5266 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_cell_refinement 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_data_reduction 'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2001)' _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^)+(0.0535P)^2^+0.4650P] 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_number_reflns 8466 _refine_ls_number_parameters 500 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0949 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1265 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL web43_23pic73_0m in P2(1)/n CELL 0.71073 9.8747 20.9315 18.7773 90.000 99.001 90.000 ZERR 4.0000 0.0008 0.0016 0.0014 0.000 0.002 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O UNIT 208 148 4 8 MERG 2 FMAP 2 GRID PLAN 1 TEMP -100 SIZE 0.06 0.12 0.26 OMIT 1 0 1 OMIT 3 3 6 CONF BOND $H HTAB O34 O13 HTAB O13 N1GA HTAB O13 N1GB OMIT -1 1 1 OMIT 0 1 1 L.S. 20 ACTA WGHT 0.053500 0.465000 FVAR 0.13789 0.68684 O13 4 0.037415 0.204613 0.759914 11.00000 0.03275 0.03228 = 0.03316 -0.00462 0.00554 -0.00210 H13 2 -0.014547 0.201268 0.796665 11.00000 0.06222 O34 4 0.308805 0.223044 0.765526 11.00000 0.03059 0.02918 = 0.03896 0.00003 -0.00187 -0.00106 H34 2 0.218232 0.211619 0.774582 11.00000 0.05950 C1 1 0.069671 0.089800 0.774591 11.00000 0.02860 0.03414 = 0.02926 0.00047 0.00485 0.00289 C2 1 0.194821 0.080457 0.817774 11.00000 0.03333 0.04389 = 0.03755 0.00177 0.00303 0.00509 AFIX 43 H2 2 0.268696 0.109157 0.815864 11.00000 -1.20000 AFIX 0 C3 1 0.210456 0.028317 0.863990 11.00000 0.04732 0.05697 = 0.03656 0.00953 0.00471 0.01648 AFIX 43 H3 2 0.295296 0.021548 0.894652 11.00000 -1.20000 AFIX 0 C4 1 0.103046 -0.013870 0.865630 11.00000 0.06566 0.04939 = 0.04903 0.02160 0.01328 0.01285 AFIX 43 H4 2 0.115712 -0.049623 0.897135 11.00000 -1.20000 AFIX 0 C5 1 -0.022586 -0.005028 0.822259 11.00000 0.05556 0.04190 = 0.04857 0.01199 0.01193 -0.00494 AFIX 43 H5 2 -0.095794 -0.034180 0.823835 11.00000 -1.20000 AFIX 0 C6 1 -0.039008 0.047457 0.776419 11.00000 0.03707 0.03677 = 0.03085 0.00102 0.00815 -0.00131 C7 1 -0.158536 0.070777 0.726584 11.00000 0.03148 0.04061 = 0.03120 -0.00228 0.00761 -0.00522 C8 1 -0.290844 0.046460 0.710071 11.00000 0.03913 0.05184 = 0.04331 -0.00122 0.00761 -0.01578 AFIX 43 H8 2 -0.314178 0.006838 0.729645 11.00000 -1.20000 AFIX 0 C9 1 -0.387905 0.081092 0.664564 11.00000 0.02925 0.07236 = 0.04635 -0.01293 0.00456 -0.01404 AFIX 43 H9 2 -0.479086 0.065447 0.653523 11.00000 -1.20000 AFIX 0 C10 1 -0.353363 0.138310 0.634991 11.00000 0.02731 0.06479 = 0.03612 -0.00566 -0.00182 0.00381 AFIX 43 H10 2 -0.421353 0.161623 0.604154 11.00000 -1.20000 AFIX 0 C11 1 -0.220196 0.162106 0.649889 11.00000 0.03088 0.04357 = 0.03368 0.00015 0.00347 0.00285 AFIX 43 H11 2 -0.196349 0.201075 0.629065 11.00000 -1.20000 AFIX 0 C12 1 -0.123582 0.127746 0.695639 11.00000 0.02401 0.03503 = 0.02729 -0.00358 0.00412 -0.00056 C13 1 0.025935 0.144967 0.722330 11.00000 0.02630 0.02718 = 0.03020 0.00008 0.00202 0.00092 C14 1 0.112127 0.148111 0.661123 11.00000 0.02225 0.03143 = 0.02868 -0.00027 0.00018 -0.00092 C15 1 0.148304 0.090905 0.633603 11.00000 0.02930 0.02957 = 0.03510 0.00040 -0.00006 -0.00093 AFIX 43 H15 2 0.119888 0.052596 0.654027 11.00000 -1.20000 AFIX 0 C16 1 0.225192 0.086018 0.576785 11.00000 0.02282 0.03649 = 0.03210 -0.00521 -0.00309 0.00260 C17 1 0.259179 0.026570 0.547890 11.00000 0.03756 0.03714 = 0.04380 -0.00811 0.00178 0.00494 AFIX 43 H17 2 0.230906 -0.012082 0.567647 11.00000 -1.20000 AFIX 0 C18 1 0.332276 0.024465 0.491854 11.00000 0.03961 0.04924 = 0.04715 -0.01270 0.00178 0.01405 AFIX 43 H18 2 0.353706 -0.015631 0.472688 11.00000 -1.20000 AFIX 0 C19 1 0.375937 0.081053 0.462394 11.00000 0.03201 0.06282 = 0.03434 -0.00680 0.00540 0.01096 AFIX 43 H19 2 0.427836 0.078855 0.423921 11.00000 -1.20000 AFIX 0 C20 1 0.344669 0.139209 0.488402 11.00000 0.02686 0.05089 = 0.03290 -0.00245 0.00214 0.00207 AFIX 43 H20 2 0.374218 0.177180 0.467758 11.00000 -1.20000 AFIX 0 C21 1 0.268106 0.143061 0.546220 11.00000 0.02205 0.03856 = 0.02875 -0.00434 -0.00043 0.00122 C22 1 0.228774 0.201779 0.574166 11.00000 0.02716 0.03329 = 0.03028 0.00041 0.00120 -0.00272 AFIX 43 H22 2 0.255340 0.240255 0.553338 11.00000 -1.20000 AFIX 0 C23 1 0.153958 0.206029 0.630006 11.00000 0.02290 0.03155 = 0.02669 -0.00164 -0.00206 -0.00134 C24 1 0.112625 0.273174 0.647254 11.00000 0.02670 0.02895 = 0.02803 0.00154 0.00670 -0.00238 C25 1 0.006070 0.298715 0.599824 11.00000 0.02831 0.03533 = 0.02930 0.00201 0.00398 -0.00128 AFIX 43 H25 2 -0.039283 0.272247 0.562414 11.00000 -1.20000 AFIX 0 C26 1 -0.039172 0.362555 0.604129 11.00000 0.02750 0.03742 = 0.03090 0.00695 0.00906 0.00339 C27 1 -0.150350 0.388348 0.555476 11.00000 0.03509 0.05178 = 0.03606 0.00924 0.00633 0.00891 AFIX 43 H27 2 -0.195736 0.362692 0.517303 11.00000 -1.20000 AFIX 0 C28 1 -0.192330 0.449540 0.563141 11.00000 0.04531 0.05745 = 0.04488 0.01700 0.01093 0.02144 AFIX 43 H28 2 -0.267578 0.466090 0.530649 11.00000 -1.20000 AFIX 0 C29 1 -0.125303 0.488444 0.618710 11.00000 0.05289 0.03888 = 0.05514 0.01121 0.01794 0.01499 AFIX 43 H29 2 -0.155824 0.531015 0.623707 11.00000 -1.20000 AFIX 0 C30 1 -0.016662 0.465443 0.665526 11.00000 0.03949 0.03432 = 0.05019 0.00323 0.01612 0.00459 AFIX 43 H30 2 0.028303 0.492269 0.702691 11.00000 -1.20000 AFIX 0 C31 1 0.029902 0.401828 0.659280 11.00000 0.02904 0.03138 = 0.03616 0.00433 0.01214 0.00116 C32 1 0.140827 0.375380 0.707135 11.00000 0.02851 0.03186 = 0.03614 -0.00368 0.00823 -0.00387 AFIX 43 H32 2 0.188076 0.401954 0.743883 11.00000 -1.20000 AFIX 0 C33 1 0.183361 0.313387 0.703063 11.00000 0.02433 0.03059 = 0.02869 0.00087 0.00499 -0.00209 C34 1 0.305700 0.291077 0.758009 11.00000 0.02536 0.02788 = 0.03286 -0.00147 0.00227 -0.00144 C35 1 0.309961 0.320792 0.833049 11.00000 0.02807 0.03172 = 0.03326 -0.00084 0.00061 0.00107 C36 1 0.213606 0.316527 0.878819 11.00000 0.03008 0.04797 = 0.03675 -0.00311 0.00427 -0.00382 AFIX 43 H36 2 0.127174 0.297039 0.863204 11.00000 -1.20000 AFIX 0 C37 1 0.245337 0.341255 0.948142 11.00000 0.04390 0.05275 = 0.03539 -0.00081 0.01160 0.00261 AFIX 43 H37 2 0.180352 0.338340 0.980343 11.00000 -1.20000 AFIX 0 C38 1 0.371054 0.370122 0.970619 11.00000 0.04637 0.04839 = 0.03040 -0.00269 -0.00180 0.00273 AFIX 43 H38 2 0.391945 0.386068 1.018446 11.00000 -1.20000 AFIX 0 C39 1 0.466540 0.376052 0.924431 11.00000 0.03564 0.04222 = 0.03610 -0.00386 -0.00566 -0.00013 AFIX 43 H39 2 0.551367 0.397143 0.939511 11.00000 -1.20000 AFIX 0 C40 1 0.435743 0.350489 0.855457 11.00000 0.02827 0.03079 = 0.03575 0.00050 -0.00014 0.00037 C41 1 0.519188 0.345172 0.797117 11.00000 0.02742 0.03196 = 0.03606 0.00121 0.00136 -0.00077 C42 1 0.652236 0.365085 0.794001 11.00000 0.03004 0.04853 = 0.04751 -0.00383 0.00025 -0.00948 AFIX 43 H42 2 0.703065 0.388155 0.832843 11.00000 -1.20000 AFIX 0 C43 1 0.709454 0.350620 0.733039 11.00000 0.02960 0.05403 = 0.05741 0.00000 0.01083 -0.00708 AFIX 43 H43 2 0.800754 0.363515 0.730344 11.00000 -1.20000 AFIX 0 C44 1 0.634803 0.317514 0.675932 11.00000 0.03727 0.04553 = 0.04784 -0.00137 0.01528 0.00100 AFIX 43 H44 2 0.675124 0.308395 0.634330 11.00000 -1.20000 AFIX 0 C45 1 0.501848 0.297616 0.679036 11.00000 0.03508 0.03927 = 0.04110 -0.00619 0.00881 0.00022 AFIX 43 H45 2 0.450838 0.274933 0.639934 11.00000 -1.20000 AFIX 0 C46 1 0.444948 0.311322 0.739866 11.00000 0.02393 0.03043 = 0.03681 -0.00111 0.00229 0.00081 PART 1 N1GA 3 -0.100305 0.192723 0.869598 21.00000 0.04465 C2GA 1 -0.236226 0.193185 0.863889 21.00000 0.04091 AFIX 43 H2GA 2 -0.287844 0.210109 0.821107 21.00000 -1.20000 AFIX 0 C3GA 1 -0.306965 0.170293 0.917012 21.00000 0.03796 C4GA 1 -0.227514 0.146083 0.977380 21.00000 0.03929 AFIX 43 H4GA 2 -0.271382 0.130165 1.015311 21.00000 -1.20000 AFIX 0 C5GA 1 -0.089955 0.143990 0.984998 21.00000 0.05033 AFIX 43 H5GA 2 -0.037176 0.126292 1.027009 21.00000 -1.20000 AFIX 0 C6GA 1 -0.027849 0.168266 0.930084 21.00000 0.05274 AFIX 43 H6GA 2 0.069376 0.167729 0.935071 21.00000 -1.20000 AFIX 0 C7GA 1 -0.458918 0.173183 0.907387 21.00000 0.06321 AFIX 137 H7A1 2 -0.495824 0.173698 0.855811 21.00000 -1.50000 H7A2 2 -0.487297 0.212075 0.930092 21.00000 -1.50000 H7A3 2 -0.493964 0.135683 0.929904 21.00000 -1.50000 PART 2 AFIX 0 N1GB 3 -0.152934 0.189675 0.861452 -21.00000 0.02871 C2GB 1 -0.130432 0.164797 0.928204 -21.00000 0.03087 C3GB 1 -0.243583 0.145667 0.965845 -21.00000 0.04647 AFIX 43 H3GB 2 -0.228419 0.126140 1.012079 -21.00000 -1.20000 AFIX 0 C4GB 1 -0.367030 0.157384 0.931267 -21.00000 0.04028 AFIX 43 H4GB 2 -0.443297 0.147045 0.954277 -21.00000 -1.20000 AFIX 0 C5GB 1 -0.392047 0.184062 0.862913 -21.00000 0.03621 AFIX 43 H5GB 2 -0.483252 0.191615 0.839770 -21.00000 -1.20000 AFIX 0 C6GB 1 -0.284172 0.199131 0.829798 -21.00000 0.03904 AFIX 43 H6GB 2 -0.301089 0.216960 0.782718 -21.00000 -1.20000 AFIX 0 C7GB 1 0.017019 0.154935 0.962380 -21.00000 0.06486 AFIX 137 H7B1 2 0.020035 0.137987 1.011255 -21.00000 -1.50000 H7B3 2 0.065786 0.195839 0.964619 -21.00000 -1.50000 H7B2 2 0.060891 0.124580 0.933438 -21.00000 -1.50000 HKLF 4 END ; 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 O13 O 0.03742(13) 0.20461(5) 0.75991(7) 0.0327(3) Uani 1 1 d . . . H13 H -0.015(2) 0.2013(10) 0.7967(12) 0.062(7) Uiso 1 1 d . . . O34 O 0.30881(13) 0.22304(6) 0.76553(6) 0.0337(3) Uani 1 1 d . . . H34 H 0.218(2) 0.2116(10) 0.7746(11) 0.059(7) Uiso 1 1 d . . . C1 C 0.06967(18) 0.08980(8) 0.77459(9) 0.0306(4) Uani 1 1 d . . . C2 C 0.1948(2) 0.08046(9) 0.81777(10) 0.0385(5) Uani 1 1 d . . . H2 H 0.2687 0.1092 0.8159 0.046 Uiso 1 1 calc R . . C3 C 0.2105(2) 0.02832(10) 0.86399(11) 0.0471(5) Uani 1 1 d . . . H3 H 0.2953 0.0215 0.8947 0.057 Uiso 1 1 calc R . . C4 C 0.1030(3) -0.01387(11) 0.86563(12) 0.0542(6) Uani 1 1 d . . . H4 H 0.1157 -0.0496 0.8971 0.065 Uiso 1 1 calc R . . C5 C -0.0226(2) -0.00503(10) 0.82226(11) 0.0483(5) Uani 1 1 d . . . H5 H -0.0958 -0.0342 0.8238 0.058 Uiso 1 1 calc R . . C6 C -0.03901(19) 0.04746(9) 0.77642(9) 0.0346(4) Uani 1 1 d . . . C7 C -0.15854(18) 0.07078(9) 0.72658(9) 0.0341(4) Uani 1 1 d . . . C8 C -0.2908(2) 0.04646(10) 0.71007(11) 0.0446(5) Uani 1 1 d . . . H8 H -0.3142 0.0068 0.7296 0.054 Uiso 1 1 calc R . . C9 C -0.3879(2) 0.08109(11) 0.66456(11) 0.0495(6) Uani 1 1 d . . . H9 H -0.4791 0.0654 0.6535 0.059 Uiso 1 1 calc R . . C10 C -0.3534(2) 0.13831(11) 0.63499(10) 0.0435(5) Uani 1 1 d . . . H10 H -0.4214 0.1616 0.6042 0.052 Uiso 1 1 calc R . . C11 C -0.22020(19) 0.16211(9) 0.64989(10) 0.0362(4) Uani 1 1 d . . . H11 H -0.1963 0.2011 0.6291 0.043 Uiso 1 1 calc R . . C12 C -0.12358(17) 0.12775(8) 0.69564(9) 0.0288(4) Uani 1 1 d . . . C13 C 0.02593(17) 0.14497(8) 0.72233(9) 0.0282(4) Uani 1 1 d . . . C14 C 0.11213(17) 0.14811(8) 0.66112(9) 0.0279(4) Uani 1 1 d . . . C15 C 0.14830(18) 0.09091(8) 0.63360(9) 0.0319(4) Uani 1 1 d . . . H15 H 0.1199 0.0526 0.6540 0.038 Uiso 1 1 calc R . . C16 C 0.22519(17) 0.08602(8) 0.57678(9) 0.0313(4) Uani 1 1 d . . . C17 C 0.2592(2) 0.02657(9) 0.54789(10) 0.0400(5) Uani 1 1 d . . . H17 H 0.2309 -0.0121 0.5676 0.048 Uiso 1 1 calc R . . C18 C 0.3323(2) 0.02447(10) 0.49185(11) 0.0459(5) Uani 1 1 d . . . H18 H 0.3537 -0.0156 0.4727 0.055 Uiso 1 1 calc R . . C19 C 0.3759(2) 0.08105(10) 0.46239(10) 0.0430(5) Uani 1 1 d . . . H19 H 0.4278 0.0789 0.4239 0.052 Uiso 1 1 calc R . . C20 C 0.34467(18) 0.13921(10) 0.48840(10) 0.0372(4) Uani 1 1 d . . . H20 H 0.3742 0.1772 0.4678 0.045 Uiso 1 1 calc R . . C21 C 0.26811(17) 0.14306(8) 0.54622(9) 0.0303(4) Uani 1 1 d . . . C22 C 0.22877(17) 0.20178(8) 0.57417(9) 0.0306(4) Uani 1 1 d . . . H22 H 0.2553 0.2403 0.5533 0.037 Uiso 1 1 calc R . . C23 C 0.15396(17) 0.20603(8) 0.63001(9) 0.0277(4) Uani 1 1 d . . . C24 C 0.11262(17) 0.27317(8) 0.64725(9) 0.0276(4) Uani 1 1 d . . . C25 C 0.00607(18) 0.29872(8) 0.59982(9) 0.0310(4) Uani 1 1 d . . . H25 H -0.0393 0.2722 0.5624 0.037 Uiso 1 1 calc R . . C26 C -0.03917(18) 0.36255(8) 0.60413(9) 0.0315(4) Uani 1 1 d . . . C27 C -0.1504(2) 0.38835(10) 0.55548(10) 0.0409(5) Uani 1 1 d . . . H27 H -0.1957 0.3627 0.5173 0.049 Uiso 1 1 calc R . . C28 C -0.1923(2) 0.44954(10) 0.56314(11) 0.0488(6) Uani 1 1 d . . . H28 H -0.2676 0.4661 0.5306 0.059 Uiso 1 1 calc R . . C29 C -0.1253(2) 0.48844(10) 0.61871(12) 0.0480(5) Uani 1 1 d . . . H29 H -0.1558 0.5310 0.6237 0.058 Uiso 1 1 calc R . . C30 C -0.0167(2) 0.46544(9) 0.66553(11) 0.0404(5) Uani 1 1 d . . . H30 H 0.0283 0.4923 0.7027 0.048 Uiso 1 1 calc R . . C31 C 0.02990(18) 0.40183(8) 0.65928(9) 0.0314(4) Uani 1 1 d . . . C32 C 0.14083(18) 0.37538(8) 0.70714(10) 0.0318(4) Uani 1 1 d . . . H32 H 0.1881 0.4020 0.7439 0.038 Uiso 1 1 calc R . . C33 C 0.18336(17) 0.31339(8) 0.70306(9) 0.0278(4) Uani 1 1 d . . . C34 C 0.30570(17) 0.29108(8) 0.75801(9) 0.0289(4) Uani 1 1 d . . . C35 C 0.30996(18) 0.32079(8) 0.83305(9) 0.0315(4) Uani 1 1 d . . . C36 C 0.21361(19) 0.31653(9) 0.87882(10) 0.0384(5) Uani 1 1 d . . . H36 H 0.1272 0.2970 0.8632 0.046 Uiso 1 1 calc R . . C37 C 0.2453(2) 0.34125(10) 0.94814(10) 0.0434(5) Uani 1 1 d . . . H37 H 0.1804 0.3383 0.9803 0.052 Uiso 1 1 calc R . . C38 C 0.3711(2) 0.37012(10) 0.97062(10) 0.0426(5) Uani 1 1 d . . . H38 H 0.3919 0.3861 1.0184 0.051 Uiso 1 1 calc R . . C39 C 0.4665(2) 0.37605(9) 0.92443(10) 0.0392(5) Uani 1 1 d . . . H39 H 0.5514 0.3971 0.9395 0.047 Uiso 1 1 calc R . . C40 C 0.43574(18) 0.35049(8) 0.85546(10) 0.0322(4) Uani 1 1 d . . . C41 C 0.51919(18) 0.34517(8) 0.79712(10) 0.0322(4) Uani 1 1 d . . . C42 C 0.6522(2) 0.36508(10) 0.79400(11) 0.0426(5) Uani 1 1 d . . . H42 H 0.7031 0.3882 0.8328 0.051 Uiso 1 1 calc R . . C43 C 0.7095(2) 0.35062(10) 0.73304(11) 0.0466(5) Uani 1 1 d . . . H43 H 0.8008 0.3635 0.7303 0.056 Uiso 1 1 calc R . . C44 C 0.6348(2) 0.31751(10) 0.67593(11) 0.0426(5) Uani 1 1 d . . . H44 H 0.6751 0.3084 0.6343 0.051 Uiso 1 1 calc R . . C45 C 0.50185(19) 0.29762(9) 0.67904(10) 0.0382(4) Uani 1 1 d . . . H45 H 0.4508 0.2749 0.6399 0.046 Uiso 1 1 calc R . . C46 C 0.44495(18) 0.31132(8) 0.73987(10) 0.0307(4) Uani 1 1 d . . . N1GA N -0.1003(4) 0.19272(13) 0.86960(16) 0.0446(9) Uiso 0.687(4) 1 d P A 1 C2GA C -0.2362(4) 0.19319(14) 0.86389(19) 0.0409(8) Uiso 0.687(4) 1 d P A 1 H2GA H -0.2878 0.2101 0.8211 0.049 Uiso 0.687(4) 1 calc PR A 1 C3GA C -0.3070(3) 0.17029(14) 0.91701(16) 0.0380(8) Uiso 0.687(4) 1 d P A 1 C4GA C -0.2275(6) 0.1461(3) 0.9774(3) 0.0393(17) Uiso 0.687(4) 1 d P A 1 H4GA H -0.2714 0.1302 1.0153 0.047 Uiso 0.687(4) 1 calc PR A 1 C5GA C -0.0900(3) 0.14399(15) 0.98500(18) 0.0503(9) Uiso 0.687(4) 1 d P A 1 H5GA H -0.0372 0.1263 1.0270 0.060 Uiso 0.687(4) 1 calc PR A 1 C6GA C -0.0278(4) 0.16827(16) 0.9301(2) 0.0527(9) Uiso 0.687(4) 1 d P A 1 H6GA H 0.0694 0.1677 0.9351 0.063 Uiso 0.687(4) 1 calc PR A 1 C7GA C -0.4589(4) 0.17318(18) 0.9074(2) 0.0632(11) Uiso 0.687(4) 1 d P A 1 H7A1 H -0.4958 0.1737 0.8558 0.095 Uiso 0.687(4) 1 calc PR A 1 H7A2 H -0.4873 0.2121 0.9301 0.095 Uiso 0.687(4) 1 calc PR A 1 H7A3 H -0.4940 0.1357 0.9299 0.095 Uiso 0.687(4) 1 calc PR A 1 N1GB N -0.1529(8) 0.1897(3) 0.8615(3) 0.0287(14) Uiso 0.313(4) 1 d P A 2 C2GB C -0.1304(6) 0.1648(3) 0.9282(3) 0.0309(15) Uiso 0.313(4) 1 d P A 2 C3GB C -0.2436(14) 0.1457(6) 0.9658(7) 0.046(4) Uiso 0.313(4) 1 d P A 2 H3GB H -0.2284 0.1261 1.0121 0.056 Uiso 0.313(4) 1 calc PR A 2 C4GB C -0.3670(8) 0.1574(3) 0.9313(4) 0.0403(17) Uiso 0.313(4) 1 d P A 2 H4GB H -0.4433 0.1470 0.9543 0.048 Uiso 0.313(4) 1 calc PR A 2 C5GB C -0.3920(7) 0.1841(3) 0.8629(3) 0.0362(17) Uiso 0.313(4) 1 d P A 2 H5GB H -0.4833 0.1916 0.8398 0.043 Uiso 0.313(4) 1 calc PR A 2 C6GB C -0.2842(7) 0.1991(3) 0.8298(4) 0.0390(16) Uiso 0.313(4) 1 d P A 2 H6GB H -0.3011 0.2170 0.7827 0.047 Uiso 0.313(4) 1 calc PR A 2 C7GB C 0.0170(9) 0.1549(4) 0.9624(5) 0.065(2) Uiso 0.313(4) 1 d P A 2 H7B1 H 0.0200 0.1380 1.0113 0.097 Uiso 0.313(4) 1 calc PR A 2 H7B3 H 0.0658 0.1958 0.9646 0.097 Uiso 0.313(4) 1 calc PR A 2 H7B2 H 0.0609 0.1246 0.9334 0.097 Uiso 0.313(4) 1 calc PR A 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 O13 0.0327(7) 0.0323(7) 0.0332(7) -0.0046(5) 0.0055(6) -0.0021(5) O34 0.0306(7) 0.0292(7) 0.0390(7) 0.0000(5) -0.0019(6) -0.0011(6) C1 0.0286(10) 0.0341(10) 0.0293(9) 0.0005(7) 0.0048(8) 0.0029(8) C2 0.0333(11) 0.0439(11) 0.0376(10) 0.0018(9) 0.0030(9) 0.0051(9) C3 0.0473(13) 0.0570(14) 0.0366(11) 0.0095(10) 0.0047(10) 0.0165(11) C4 0.0657(16) 0.0494(13) 0.0490(13) 0.0216(10) 0.0133(12) 0.0129(12) C5 0.0556(15) 0.0419(12) 0.0486(12) 0.0120(10) 0.0119(11) -0.0049(10) C6 0.0371(11) 0.0368(10) 0.0309(10) 0.0010(8) 0.0082(9) -0.0013(8) C7 0.0315(10) 0.0406(11) 0.0312(10) -0.0023(8) 0.0076(8) -0.0052(8) C8 0.0391(12) 0.0518(13) 0.0433(12) -0.0012(10) 0.0076(10) -0.0158(10) C9 0.0293(11) 0.0724(16) 0.0463(12) -0.0129(11) 0.0046(10) -0.0140(11) C10 0.0273(11) 0.0648(14) 0.0361(11) -0.0057(10) -0.0018(9) 0.0038(10) C11 0.0309(11) 0.0436(11) 0.0337(10) 0.0001(8) 0.0035(8) 0.0029(8) C12 0.0240(9) 0.0350(10) 0.0273(9) -0.0036(7) 0.0041(7) -0.0006(8) C13 0.0263(9) 0.0272(9) 0.0302(9) 0.0001(7) 0.0020(8) 0.0009(7) C14 0.0222(9) 0.0314(10) 0.0287(9) -0.0003(7) 0.0002(7) -0.0009(7) C15 0.0293(10) 0.0296(10) 0.0351(10) 0.0004(8) -0.0001(8) -0.0009(8) C16 0.0228(9) 0.0365(10) 0.0321(10) -0.0052(8) -0.0031(8) 0.0026(8) C17 0.0376(11) 0.0371(11) 0.0438(11) -0.0081(9) 0.0018(9) 0.0049(9) C18 0.0396(12) 0.0492(13) 0.0472(12) -0.0127(10) 0.0018(10) 0.0140(10) C19 0.0320(11) 0.0628(14) 0.0343(11) -0.0068(10) 0.0054(9) 0.0110(10) C20 0.0269(10) 0.0509(12) 0.0329(10) -0.0025(9) 0.0021(8) 0.0021(9) C21 0.0221(9) 0.0386(10) 0.0288(9) -0.0043(8) -0.0004(8) 0.0012(7) C22 0.0272(9) 0.0333(10) 0.0303(9) 0.0004(8) 0.0012(8) -0.0027(8) C23 0.0229(9) 0.0315(10) 0.0267(9) -0.0016(7) -0.0021(7) -0.0013(7) C24 0.0267(9) 0.0290(9) 0.0280(9) 0.0015(7) 0.0067(8) -0.0024(7) C25 0.0283(10) 0.0353(10) 0.0293(9) 0.0020(7) 0.0040(8) -0.0013(8) C26 0.0275(10) 0.0374(10) 0.0309(9) 0.0069(8) 0.0091(8) 0.0034(8) C27 0.0351(11) 0.0518(13) 0.0361(11) 0.0092(9) 0.0063(9) 0.0089(9) C28 0.0453(13) 0.0574(14) 0.0449(12) 0.0170(10) 0.0109(10) 0.0214(11) C29 0.0529(14) 0.0389(12) 0.0551(13) 0.0112(10) 0.0179(12) 0.0150(10) C30 0.0395(12) 0.0343(11) 0.0502(12) 0.0032(9) 0.0161(10) 0.0046(9) C31 0.0290(10) 0.0314(10) 0.0362(10) 0.0043(8) 0.0121(8) 0.0012(8) C32 0.0285(10) 0.0319(10) 0.0361(10) -0.0037(8) 0.0082(8) -0.0039(8) C33 0.0243(9) 0.0306(10) 0.0287(9) 0.0009(7) 0.0050(7) -0.0021(7) C34 0.0254(9) 0.0279(9) 0.0329(9) -0.0015(7) 0.0023(8) -0.0014(7) C35 0.0281(10) 0.0317(10) 0.0333(10) -0.0008(8) 0.0006(8) 0.0011(8) C36 0.0301(11) 0.0480(12) 0.0368(11) -0.0031(9) 0.0043(9) -0.0038(9) C37 0.0439(13) 0.0527(13) 0.0354(11) -0.0008(9) 0.0116(10) 0.0026(10) C38 0.0464(13) 0.0484(12) 0.0304(10) -0.0027(9) -0.0018(9) 0.0027(10) C39 0.0356(11) 0.0422(11) 0.0361(11) -0.0039(8) -0.0057(9) -0.0001(9) C40 0.0283(10) 0.0308(10) 0.0358(10) 0.0005(8) -0.0001(8) 0.0004(8) C41 0.0274(10) 0.0320(10) 0.0361(10) 0.0012(8) 0.0014(8) -0.0008(8) C42 0.0300(11) 0.0485(12) 0.0475(12) -0.0038(9) 0.0003(9) -0.0095(9) C43 0.0296(11) 0.0540(13) 0.0574(14) 0.0000(10) 0.0108(10) -0.0071(9) C44 0.0373(12) 0.0455(12) 0.0478(12) -0.0014(9) 0.0153(10) 0.0010(9) C45 0.0351(11) 0.0393(11) 0.0411(11) -0.0062(8) 0.0088(9) 0.0002(8) C46 0.0239(9) 0.0304(10) 0.0368(10) -0.0011(8) 0.0023(8) 0.0008(7) _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 O13 C13 1.430(2) . ? O13 H13 0.92(2) . ? O34 C34 1.431(2) . ? O34 H34 0.97(2) . ? C1 C2 1.382(2) . ? C1 C6 1.396(2) . ? C1 C13 1.533(2) . ? C2 C3 1.388(3) . ? C2 H2 0.9500 . ? C3 C4 1.384(3) . ? C3 H3 0.9500 . ? C4 C5 1.386(3) . ? C4 H4 0.9500 . ? C5 C6 1.389(3) . ? C5 H5 0.9500 . ? C6 C7 1.470(3) . ? C7 C8 1.391(3) . ? C7 C12 1.393(2) . ? C8 C9 1.385(3) . ? C8 H8 0.9500 . ? C9 C10 1.385(3) . ? C9 H9 0.9500 . ? C10 C11 1.393(3) . ? C10 H10 0.9500 . ? C11 C12 1.382(2) . ? C11 H11 0.9500 . ? C12 C13 1.526(2) . ? C13 C14 1.535(2) . ? C14 C15 1.373(2) . ? C14 C23 1.434(2) . ? C15 C16 1.407(2) . ? C15 H15 0.9500 . ? C16 C21 1.418(2) . ? C16 C17 1.419(2) . ? C17 C18 1.367(3) . ? C17 H17 0.9500 . ? C18 C19 1.403(3) . ? C18 H18 0.9500 . ? C19 C20 1.365(3) . ? C19 H19 0.9500 . ? C20 C21 1.419(2) . ? C20 H20 0.9500 . ? C21 C22 1.414(2) . ? C22 C23 1.377(2) . ? C22 H22 0.9500 . ? C23 C24 1.513(2) . ? C24 C25 1.376(2) . ? C24 C33 1.437(2) . ? C25 C26 1.415(2) . ? C25 H25 0.9500 . ? C26 C31 1.412(3) . ? C26 C27 1.420(3) . ? C27 C28 1.361(3) . ? C27 H27 0.9500 . ? C28 C29 1.405(3) . ? C28 H28 0.9500 . ? C29 C30 1.364(3) . ? C29 H29 0.9500 . ? C30 C31 1.420(2) . ? C30 H30 0.9500 . ? C31 C32 1.416(3) . ? C32 C33 1.370(2) . ? C32 H32 0.9500 . ? C33 C34 1.534(2) . ? C34 C46 1.527(2) . ? C34 C35 1.535(2) . ? C35 C36 1.381(2) . ? C35 C40 1.394(2) . ? C36 C37 1.390(3) . ? C36 H36 0.9500 . ? C37 C38 1.386(3) . ? C37 H37 0.9500 . ? C38 C39 1.383(3) . ? C38 H38 0.9500 . ? C39 C40 1.390(2) . ? C39 H39 0.9500 . ? C40 C41 1.474(2) . ? C41 C42 1.388(2) . ? C41 C46 1.396(2) . ? C42 C43 1.387(3) . ? C42 H42 0.9500 . ? C43 C44 1.388(3) . ? C43 H43 0.9500 . ? C44 C45 1.387(3) . ? C44 H44 0.9500 . ? C45 C46 1.380(2) . ? C45 H45 0.9500 . ? N1GA C2GA 1.330(4) . ? N1GA C6GA 1.345(5) . ? C2GA C3GA 1.389(5) . ? C2GA H2GA 0.9500 . ? C3GA C4GA 1.371(6) . ? C3GA C7GA 1.484(5) . ? C4GA C5GA 1.344(6) . ? C4GA H4GA 0.9500 . ? C5GA C6GA 1.377(5) . ? C5GA H5GA 0.9500 . ? C6GA H6GA 0.9500 . ? C7GA H7A1 0.9800 . ? C7GA H7A2 0.9800 . ? C7GA H7A3 0.9800 . ? N1GB C2GB 1.343(8) . ? N1GB C6GB 1.353(10) . ? C2GB C3GB 1.468(15) . ? C2GB C7GB 1.511(11) . ? C3GB C4GB 1.311(15) . ? C3GB H3GB 0.9500 . ? C4GB C5GB 1.386(9) . ? C4GB H4GB 0.9500 . ? C5GB C6GB 1.352(9) . ? C5GB H5GB 0.9500 . ? C6GB H6GB 0.9500 . ? C7GB H7B1 0.9800 . ? C7GB H7B3 0.9800 . ? C7GB H7B2 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O13 H13 107.0(14) . . ? C34 O34 H34 104.9(13) . . ? C2 C1 C6 121.06(17) . . ? C2 C1 C13 128.22(16) . . ? C6 C1 C13 110.68(15) . . ? C1 C2 C3 118.69(19) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 120.3(2) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 121.36(19) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C4 C5 C6 118.47(19) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? C5 C6 C1 120.09(18) . . ? C5 C6 C7 131.39(18) . . ? C1 C6 C7 108.49(15) . . ? C8 C7 C12 120.36(18) . . ? C8 C7 C6 130.75(18) . . ? C12 C7 C6 108.84(16) . . ? C9 C8 C7 118.76(19) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C8 C9 C10 120.66(19) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C9 C10 C11 120.84(19) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 118.49(18) . . ? C12 C11 H11 120.8 . . ? C10 C11 H11 120.8 . . ? C11 C12 C7 120.85(17) . . ? C11 C12 C13 128.29(16) . . ? C7 C12 C13 110.81(15) . . ? O13 C13 C12 111.48(13) . . ? O13 C13 C1 110.43(14) . . ? C12 C13 C1 101.16(13) . . ? O13 C13 C14 108.77(13) . . ? C12 C13 C14 112.68(14) . . ? C1 C13 C14 112.20(14) . . ? C15 C14 C23 118.37(15) . . ? C15 C14 C13 116.86(15) . . ? C23 C14 C13 124.75(15) . . ? C14 C15 C16 123.49(17) . . ? C14 C15 H15 118.3 . . ? C16 C15 H15 118.3 . . ? C15 C16 C21 118.47(16) . . ? C15 C16 C17 122.82(17) . . ? C21 C16 C17 118.70(16) . . ? C18 C17 C16 120.52(19) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 120.54(18) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C20 C19 C18 120.74(18) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C19 C20 C21 120.12(18) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C22 C21 C16 117.69(15) . . ? C22 C21 C20 122.91(17) . . ? C16 C21 C20 119.38(16) . . ? C23 C22 C21 123.36(16) . . ? C23 C22 H22 118.3 . . ? C21 C22 H22 118.3 . . ? C22 C23 C14 118.60(15) . . ? C22 C23 C24 114.71(14) . . ? C14 C23 C24 126.41(14) . . ? C25 C24 C33 118.66(16) . . ? C25 C24 C23 115.28(15) . . ? C33 C24 C23 125.71(15) . . ? C24 C25 C26 123.11(16) . . ? C24 C25 H25 118.4 . . ? C26 C25 H25 118.4 . . ? C31 C26 C25 118.11(16) . . ? C31 C26 C27 119.12(17) . . ? C25 C26 C27 122.77(17) . . ? C28 C27 C26 120.5(2) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? C27 C28 C29 120.5(2) . . ? C27 C28 H28 119.7 . . ? C29 C28 H28 119.7 . . ? C30 C29 C28 120.38(19) . . ? C30 C29 H29 119.8 . . ? C28 C29 H29 119.8 . . ? C29 C30 C31 120.67(19) . . ? C29 C30 H30 119.7 . . ? C31 C30 H30 119.7 . . ? C26 C31 C32 118.35(16) . . ? C26 C31 C30 118.77(17) . . ? C32 C31 C30 122.86(17) . . ? C33 C32 C31 123.26(17) . . ? C33 C32 H32 118.4 . . ? C31 C32 H32 118.4 . . ? C32 C33 C24 118.51(16) . . ? C32 C33 C34 117.84(15) . . ? C24 C33 C34 123.64(15) . . ? O34 C34 C46 106.98(13) . . ? O34 C34 C33 111.83(13) . . ? C46 C34 C33 114.04(14) . . ? O34 C34 C35 108.40(13) . . ? C46 C34 C35 101.30(14) . . ? C33 C34 C35 113.57(14) . . ? C36 C35 C40 120.60(17) . . ? C36 C35 C34 128.50(16) . . ? C40 C35 C34 110.67(15) . . ? C35 C36 C37 118.83(18) . . ? C35 C36 H36 120.6 . . ? C37 C36 H36 120.6 . . ? C38 C37 C36 120.49(18) . . ? C38 C37 H37 119.8 . . ? C36 C37 H37 119.8 . . ? C39 C38 C37 120.95(18) . . ? C39 C38 H38 119.5 . . ? C37 C38 H38 119.5 . . ? C38 C39 C40 118.58(18) . . ? C38 C39 H39 120.7 . . ? C40 C39 H39 120.7 . . ? C39 C40 C35 120.50(17) . . ? C39 C40 C41 130.92(17) . . ? C35 C40 C41 108.50(15) . . ? C42 C41 C46 120.42(17) . . ? C42 C41 C40 130.63(17) . . ? C46 C41 C40 108.86(15) . . ? C43 C42 C41 118.66(18) . . ? C43 C42 H42 120.7 . . ? C41 C42 H42 120.7 . . ? C42 C43 C44 120.73(18) . . ? C42 C43 H43 119.6 . . ? C44 C43 H43 119.6 . . ? C45 C44 C43 120.61(18) . . ? C45 C44 H44 119.7 . . ? C43 C44 H44 119.7 . . ? C46 C45 C44 118.88(18) . . ? C46 C45 H45 120.6 . . ? C44 C45 H45 120.6 . . ? C45 C46 C41 120.68(17) . . ? C45 C46 C34 128.64(16) . . ? C41 C46 C34 110.59(15) . . ? C2GA N1GA C6GA 117.9(3) . . ? N1GA C2GA C3GA 123.6(3) . . ? N1GA C2GA H2GA 118.2 . . ? C3GA C2GA H2GA 118.2 . . ? C4GA C3GA C2GA 115.7(4) . . ? C4GA C3GA C7GA 123.6(4) . . ? C2GA C3GA C7GA 120.7(3) . . ? C5GA C4GA C3GA 122.6(5) . . ? C5GA C4GA H4GA 118.7 . . ? C3GA C4GA H4GA 118.7 . . ? C4GA C5GA C6GA 118.0(4) . . ? C4GA C5GA H5GA 121.0 . . ? C6GA C5GA H5GA 121.0 . . ? N1GA C6GA C5GA 122.2(4) . . ? N1GA C6GA H6GA 118.9 . . ? C5GA C6GA H6GA 118.9 . . ? C2GB N1GB C6GB 118.3(7) . . ? N1GB C2GB C3GB 121.8(8) . . ? N1GB C2GB C7GB 117.2(6) . . ? C3GB C2GB C7GB 120.9(7) . . ? C4GB C3GB C2GB 115.4(10) . . ? C4GB C3GB H3GB 122.3 . . ? C2GB C3GB H3GB 122.3 . . ? C3GB C4GB C5GB 123.4(9) . . ? C3GB C4GB H4GB 118.3 . . ? C5GB C4GB H4GB 118.3 . . ? C6GB C5GB C4GB 118.7(7) . . ? C6GB C5GB H5GB 120.6 . . ? C4GB C5GB H5GB 120.6 . . ? C5GB C6GB N1GB 122.2(7) . . ? C5GB C6GB H6GB 118.9 . . ? N1GB C6GB H6GB 118.9 . . ? C2GB C7GB H7B1 109.5 . . ? C2GB C7GB H7B3 109.5 . . ? H7B1 C7GB H7B3 109.5 . . ? C2GB C7GB H7B2 109.5 . . ? H7B1 C7GB H7B2 109.5 . . ? H7B3 C7GB H7B2 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.8(3) . . . . ? C13 C1 C2 C3 176.96(17) . . . . ? C1 C2 C3 C4 1.0(3) . . . . ? C2 C3 C4 C5 -0.8(3) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? C4 C5 C6 C1 0.2(3) . . . . ? C4 C5 C6 C7 -177.65(19) . . . . ? C2 C1 C6 C5 0.2(3) . . . . ? C13 C1 C6 C5 -177.92(17) . . . . ? C2 C1 C6 C7 178.42(16) . . . . ? C13 C1 C6 C7 0.34(19) . . . . ? C5 C6 C7 C8 -0.8(3) . . . . ? C1 C6 C7 C8 -178.81(19) . . . . ? C5 C6 C7 C12 176.8(2) . . . . ? C1 C6 C7 C12 -1.2(2) . . . . ? C12 C7 C8 C9 -2.4(3) . . . . ? C6 C7 C8 C9 175.05(18) . . . . ? C7 C8 C9 C10 1.1(3) . . . . ? C8 C9 C10 C11 0.5(3) . . . . ? C9 C10 C11 C12 -0.8(3) . . . . ? C10 C11 C12 C7 -0.4(3) . . . . ? C10 C11 C12 C13 -177.36(16) . . . . ? C8 C7 C12 C11 2.0(3) . . . . ? C6 C7 C12 C11 -175.92(16) . . . . ? C8 C7 C12 C13 179.47(16) . . . . ? C6 C7 C12 C13 1.54(19) . . . . ? C11 C12 C13 O13 58.6(2) . . . . ? C7 C12 C13 O13 -118.65(16) . . . . ? C11 C12 C13 C1 175.96(17) . . . . ? C7 C12 C13 C1 -1.26(17) . . . . ? C11 C12 C13 C14 -64.1(2) . . . . ? C7 C12 C13 C14 118.73(16) . . . . ? C2 C1 C13 O13 -59.2(2) . . . . ? C6 C1 C13 O13 118.67(16) . . . . ? C2 C1 C13 C12 -177.38(17) . . . . ? C6 C1 C13 C12 0.52(18) . . . . ? C2 C1 C13 C14 62.3(2) . . . . ? C6 C1 C13 C14 -119.80(16) . . . . ? O13 C13 C14 C15 160.53(15) . . . . ? C12 C13 C14 C15 -75.33(19) . . . . ? C1 C13 C14 C15 38.1(2) . . . . ? O13 C13 C14 C23 -21.1(2) . . . . ? C12 C13 C14 C23 103.08(19) . . . . ? C1 C13 C14 C23 -143.53(16) . . . . ? C23 C14 C15 C16 0.5(3) . . . . ? C13 C14 C15 C16 179.01(16) . . . . ? C14 C15 C16 C21 0.1(3) . . . . ? C14 C15 C16 C17 -178.57(17) . . . . ? C15 C16 C17 C18 178.93(18) . . . . ? C21 C16 C17 C18 0.2(3) . . . . ? C16 C17 C18 C19 0.6(3) . . . . ? C17 C18 C19 C20 -0.9(3) . . . . ? C18 C19 C20 C21 0.5(3) . . . . ? C15 C16 C21 C22 -1.0(2) . . . . ? C17 C16 C21 C22 177.75(16) . . . . ? C15 C16 C21 C20 -179.41(16) . . . . ? C17 C16 C21 C20 -0.7(3) . . . . ? C19 C20 C21 C22 -178.01(17) . . . . ? C19 C20 C21 C16 0.3(3) . . . . ? C16 C21 C22 C23 1.3(3) . . . . ? C20 C21 C22 C23 179.68(17) . . . . ? C21 C22 C23 C14 -0.7(3) . . . . ? C21 C22 C23 C24 -175.02(16) . . . . ? C15 C14 C23 C22 -0.2(2) . . . . ? C13 C14 C23 C22 -178.59(16) . . . . ? C15 C14 C23 C24 173.35(16) . . . . ? C13 C14 C23 C24 -5.0(3) . . . . ? C22 C23 C24 C25 76.0(2) . . . . ? C14 C23 C24 C25 -97.8(2) . . . . ? C22 C23 C24 C33 -97.14(19) . . . . ? C14 C23 C24 C33 89.1(2) . . . . ? C33 C24 C25 C26 -1.2(2) . . . . ? C23 C24 C25 C26 -174.85(15) . . . . ? C24 C25 C26 C31 0.8(2) . . . . ? C24 C25 C26 C27 -179.22(16) . . . . ? C31 C26 C27 C28 -1.9(3) . . . . ? C25 C26 C27 C28 178.17(17) . . . . ? C26 C27 C28 C29 0.8(3) . . . . ? C27 C28 C29 C30 0.3(3) . . . . ? C28 C29 C30 C31 -0.4(3) . . . . ? C25 C26 C31 C32 0.2(2) . . . . ? C27 C26 C31 C32 -179.77(16) . . . . ? C25 C26 C31 C30 -178.29(16) . . . . ? C27 C26 C31 C30 1.7(2) . . . . ? C29 C30 C31 C26 -0.6(3) . . . . ? C29 C30 C31 C32 -179.03(17) . . . . ? C26 C31 C32 C33 -0.8(2) . . . . ? C30 C31 C32 C33 177.63(16) . . . . ? C31 C32 C33 C24 0.4(2) . . . . ? C31 C32 C33 C34 179.54(15) . . . . ? C25 C24 C33 C32 0.6(2) . . . . ? C23 C24 C33 C32 173.51(15) . . . . ? C25 C24 C33 C34 -178.49(15) . . . . ? C23 C24 C33 C34 -5.6(3) . . . . ? C32 C33 C34 O34 158.88(14) . . . . ? C24 C33 C34 O34 -22.0(2) . . . . ? C32 C33 C34 C46 -79.58(19) . . . . ? C24 C33 C34 C46 99.54(18) . . . . ? C32 C33 C34 C35 35.8(2) . . . . ? C24 C33 C34 C35 -145.08(16) . . . . ? O34 C34 C35 C36 -64.8(2) . . . . ? C46 C34 C35 C36 -177.17(18) . . . . ? C33 C34 C35 C36 60.1(2) . . . . ? O34 C34 C35 C40 109.63(16) . . . . ? C46 C34 C35 C40 -2.72(18) . . . . ? C33 C34 C35 C40 -125.43(16) . . . . ? C40 C35 C36 C37 -1.3(3) . . . . ? C34 C35 C36 C37 172.71(17) . . . . ? C35 C36 C37 C38 0.5(3) . . . . ? C36 C37 C38 C39 1.2(3) . . . . ? C37 C38 C39 C40 -2.1(3) . . . . ? C38 C39 C40 C35 1.4(3) . . . . ? C38 C39 C40 C41 -174.91(18) . . . . ? C36 C35 C40 C39 0.3(3) . . . . ? C34 C35 C40 C39 -174.65(16) . . . . ? C36 C35 C40 C41 177.36(16) . . . . ? C34 C35 C40 C41 2.4(2) . . . . ? C39 C40 C41 C42 -1.1(3) . . . . ? C35 C40 C41 C42 -177.70(19) . . . . ? C39 C40 C41 C46 175.63(19) . . . . ? C35 C40 C41 C46 -1.0(2) . . . . ? C46 C41 C42 C43 0.0(3) . . . . ? C40 C41 C42 C43 176.34(19) . . . . ? C41 C42 C43 C44 0.7(3) . . . . ? C42 C43 C44 C45 -0.7(3) . . . . ? C43 C44 C45 C46 0.0(3) . . . . ? C44 C45 C46 C41 0.6(3) . . . . ? C44 C45 C46 C34 -175.68(17) . . . . ? C42 C41 C46 C45 -0.6(3) . . . . ? C40 C41 C46 C45 -177.71(16) . . . . ? C42 C41 C46 C34 176.29(16) . . . . ? C40 C41 C46 C34 -0.8(2) . . . . ? O34 C34 C46 C45 65.2(2) . . . . ? C33 C34 C46 C45 -58.9(2) . . . . ? C35 C34 C46 C45 178.67(18) . . . . ? O34 C34 C46 C41 -111.35(15) . . . . ? C33 C34 C46 C41 124.46(16) . . . . ? C35 C34 C46 C41 2.08(18) . . . . ? C6GA N1GA C2GA C3GA 0.5(5) . . . . ? N1GA C2GA C3GA C4GA -0.4(5) . . . . ? N1GA C2GA C3GA C7GA 179.1(3) . . . . ? C2GA C3GA C4GA C5GA -0.5(6) . . . . ? C7GA C3GA C4GA C5GA -179.9(4) . . . . ? C3GA C4GA C5GA C6GA 1.1(7) . . . . ? C2GA N1GA C6GA C5GA 0.2(5) . . . . ? C4GA C5GA C6GA N1GA -1.0(5) . . . . ? C6GB N1GB C2GB C3GB 2.4(10) . . . . ? C6GB N1GB C2GB C7GB -179.8(6) . . . . ? N1GB C2GB C3GB C4GB -3.1(14) . . . . ? C7GB C2GB C3GB C4GB 179.1(8) . . . . ? C2GB C3GB C4GB C5GB 2.0(14) . . . . ? C3GB C4GB C5GB C6GB -0.2(11) . . . . ? C4GB C5GB C6GB N1GB -0.7(9) . . . . ? C2GB N1GB C6GB C5GB -0.4(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O34 H34 O13 0.97(2) 1.77(2) 2.6932(18) 158.8(19) . O13 H13 N1GA 0.92(2) 1.73(2) 2.651(3) 175(2) . O13 H13 N1GB 0.92(2) 1.98(2) 2.896(7) 170(2) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.13 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.236 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.040 _database_code_depnum_ccdc_archive 'CCDC 945703'