Electronic Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Jeremy Robertson' 'Stephen J. Bell' 'Alexander Krivokapic' _publ_contact_author_name 'Jeremy Robertson' _publ_contact_author_address ; Department of Chemistry University of Oxford Chemistry Research Laboratory Mans Mansfield Road Oxford OX1 3TA UNITED KINGDOM ; _publ_contact_author_email JEREMY.ROBERTSON@CHEM.OX.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; On the Reaction of Diphenylketene with Isocyanides ; data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 283680' _audit_creation_date 05-27-08 _audit_creation_method CRYSTALS_ver_12-03-99 _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; H atoms placed geometrically after each cycle ; _publ_section_exptl_prep ; ? ; #========================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment noref #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 15.3223(4) _cell_angle_alpha 90 _cell_length_b 12.7909(3) _cell_angle_beta 104.8195(12) _cell_length_c 14.0095(5) _cell_angle_gamma 90 _cell_volume 2654.34(13) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 c 1 ' _symmetry_space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,y+1/2,z x,-y,z+1/2 x+1/2,-y+1/2,z+1/2 # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum ' C33 H29 N1 O2 ' _chemical_formula_moiety ' C33 H29 N1 O2 ' _chemical_compound_source ; ? ; _chemical_formula_weight 471.60 _cell_measurement_reflns_used 2908 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' yellow ' _exptl_crystal_size_min 0.02 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.15 _exptl_crystal_density_diffrn 1.180 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1000.000 _exptl_absorpt_coefficient_mu 0.073 # Sheldrick geometric definitions 0.99 1.00 _diffrn_measurement_device_type ; Enraf Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 1.00 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 5740 _reflns_number_total 3035 _diffrn_reflns_av_R_equivalents 0.01 # Number of reflections with Friedels Law is 3035 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3044 _diffrn_reflns_theta_min 2.104 _diffrn_reflns_theta_max 27.508 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.508 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -19 _reflns_limit_h_max 19 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _refine_diff_density_min -0.29 _refine_diff_density_max 0.52 _refine_ls_number_reflns 1857 _refine_ls_number_parameters 109 #_refine_ls_R_factor_ref 0.0509 _refine_ls_wR_factor_ref 0.0508 _refine_ls_goodness_of_fit_ref 1.0101 #_reflns_number_all 3035 _refine_ls_R_factor_all 0.0952 _refine_ls_wR_factor_all 0.1048 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 1857 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_gt 0.0508 _refine_ls_shift/su_max 0.000128 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 1.73 0.271 0.578 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 COLLECT Software, Nonius BV 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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_occupancy _atom_site_adp_type _atom_site_attached_hydrogens C1 C 0.7578(4) 0.0432(4) 0.2127(4) 0.0219 1.0000 Uani . C2 C 0.7082(4) 0.0838(4) 0.2693(5) 0.0270 1.0000 Uani . C3 C 0.7026(4) 0.1951(4) 0.2922(4) 0.0217 1.0000 Uani . C4 C 0.6260(4) 0.2330(4) 0.3088(4) 0.0286 1.0000 Uani . C5 C 0.6195(4) 0.3410(5) 0.3313(4) 0.0322 1.0000 Uani . C6 C 0.6887(4) 0.4052(5) 0.3357(5) 0.0368 1.0000 Uani . C7 C 0.7689(4) 0.3681(5) 0.3186(4) 0.0299 1.0000 Uani . C8 C 0.7769(4) 0.2618(5) 0.2992(5) 0.0359 1.0000 Uani . C9 C 0.6500(4) 0.0072(4) 0.3106(4) 0.0216 1.0000 Uani . C10 C 0.5778(4) -0.0422(5) 0.2470(4) 0.0345 1.0000 Uani . C11 C 0.5226(5) -0.1064(5) 0.2844(5) 0.0440 1.0000 Uani . C12 C 0.5403(4) -0.1213(5) 0.3902(5) 0.0376 1.0000 Uani . C13 C 0.6134(4) -0.0729(6) 0.4500(5) 0.0393 1.0000 Uani . C14 C 0.6686(4) -0.0068(5) 0.4118(5) 0.0372 1.0000 Uani . C15 C 0.7755(4) -0.0604(3) 0.1928(4) 0.0232 1.0000 Uani . O16 O 0.8400(3) -0.0608(3) 0.1335(3) 0.0374 1.0000 Uani . C17 C 0.8551(4) 0.0462(4) 0.1173(5) 0.0282 1.0000 Uani . O18 O 0.8070(4) 0.10652(16) 0.1631(4) 0.0283 1.0000 Uani . C19 C 0.9063(4) 0.0813(4) 0.0603(4) 0.0221 1.0000 Uani . C20 C 0.9621(4) 0.0103(4) 0.0204(5) 0.0267 1.0000 Uani . C21 C 0.9482(4) -0.0063(4) -0.0818(4) 0.0265 1.0000 Uani . C22 C 1.0036(5) -0.0726(5) -0.1188(5) 0.0395 1.0000 Uani . C23 C 1.0758(5) -0.1222(5) -0.0522(6) 0.0420 1.0000 Uani . C24 C 1.0912(5) -0.1074(5) 0.0430(6) 0.0520 1.0000 Uani . C25 C 1.0353(5) -0.0418(6) 0.0811(5) 0.0431 1.0000 Uani . C26 C 0.9088(4) 0.1954(5) 0.0391(4) 0.0264 1.0000 Uani . C27 C 0.9900(3) 0.2405(4) 0.0213(4) 0.0256 1.0000 Uani . C28 C 0.9971(4) 0.3434(5) 0.0023(4) 0.0317 1.0000 Uani . C29 C 0.9217(4) 0.4108(4) -0.0028(5) 0.0305 1.0000 Uani . C30 C 0.8426(5) 0.3694(5) 0.0113(5) 0.0457 1.0000 Uani . C31 C 0.8375(4) 0.2655(5) 0.0318(5) 0.0327 1.0000 Uani . N32 N 0.7517(2) -0.1511(3) 0.2128(2) 0.0281 1.0000 Uani . C33 C 0.7808(3) -0.2557(3) 0.1874(3) 0.0317 1.0000 Uani . C34 C 0.8750(5) -0.2693(5) 0.2409(5) 0.0650 1.0000 Uani . C35 C 0.7544(5) -0.2693(5) 0.0807(4) 0.0532 1.0000 Uani . C36 C 0.7240(4) -0.3331(4) 0.2288(4) 0.0473 1.0000 Uani . H41 H 0.5728 0.1869 0.3092 0.0374 1.0000 Uiso . H51 H 0.5618 0.3689 0.3415 0.0366 1.0000 Uiso . H61 H 0.6799 0.4807 0.3491 0.0356 1.0000 Uiso . H71 H 0.8198 0.4158 0.3204 0.0319 1.0000 Uiso . H81 H 0.8355 0.2353 0.2910 0.0491 1.0000 Uiso . H101 H 0.5652 -0.0320 0.1726 0.0480 1.0000 Uiso . H111 H 0.4701 -0.1396 0.2381 0.0506 1.0000 Uiso . H121 H 0.5017 -0.1733 0.4189 0.0576 1.0000 Uiso . H131 H 0.6272 -0.0815 0.5253 0.0479 1.0000 Uiso . H141 H 0.7247 0.0291 0.4611 0.0517 1.0000 Uiso . H211 H 0.8992 0.0323 -0.1273 0.0283 1.0000 Uiso . H221 H 0.9931 -0.0879 -0.1895 0.0516 1.0000 Uiso . H231 H 1.1177 -0.1653 -0.0801 0.0423 1.0000 Uiso . H241 H 1.1447 -0.1474 0.0884 0.0802 1.0000 Uiso . H251 H 1.0475 -0.0293 0.1541 0.0514 1.0000 Uiso . H271 H 1.0431 0.1908 0.0263 0.0306 1.0000 Uiso . H281 H 1.0553 0.3729 -0.0116 0.0405 1.0000 Uiso . H291 H 0.9232 0.4900 -0.0175 0.0442 1.0000 Uiso . H301 H 0.7857 0.4189 0.0065 0.0592 1.0000 Uiso . H311 H 0.7781 0.2336 0.0419 0.0372 1.0000 Uiso . H341 H 0.8979 -0.3400 0.2218 0.0573 1.0000 Uiso . H342 H 0.9136 -0.2140 0.2180 0.0573 1.0000 Uiso . H343 H 0.8840 -0.2657 0.3116 0.0573 1.0000 Uiso . H351 H 0.7763 -0.3383 0.0573 0.0610 1.0000 Uiso . H352 H 0.7858 -0.2121 0.0452 0.0610 1.0000 Uiso . H353 H 0.6890 -0.2625 0.0497 0.0610 1.0000 Uiso . H361 H 0.7378 -0.4071 0.2165 0.0621 1.0000 Uiso . H362 H 0.7343 -0.3227 0.3030 0.0621 1.0000 Uiso . H363 H 0.6572 -0.3201 0.1981 0.0621 1.0000 Uiso . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0175 0.0285 0.0239 0.0103 0.0132 -0.0035 C2 0.0164 0.0282 0.0401 -0.0000 0.0143 -0.0041 C3 0.0258 0.0242 0.0160 -0.0086 0.0073 -0.0017 C4 0.0375 0.0232 0.0266 0.0020 0.0110 -0.0038 C5 0.0392 0.0258 0.0323 -0.0021 0.0103 0.0126 C6 0.0421 0.0353 0.0331 -0.0047 0.0099 0.0064 C7 0.0279 0.0308 0.0340 -0.0077 0.0136 -0.0068 C8 0.0290 0.0336 0.0420 -0.0045 0.0033 0.0025 C9 0.0210 0.0273 0.0211 0.0064 0.0135 0.0007 C10 0.0231 0.0461 0.0367 -0.0160 0.0119 -0.0138 C11 0.0335 0.0535 0.0445 -0.0133 0.0091 -0.0141 C12 0.0435 0.0238 0.0543 0.0107 0.0285 0.0081 C13 0.0474 0.0370 0.0372 0.0043 0.0174 0.0126 C14 0.0319 0.0298 0.0523 0.0124 0.0149 0.0084 C15 0.0289 0.0082 0.0278 0.0070 -0.0015 -0.0084 O16 0.0262 0.0498 0.0380 -0.0046 0.0115 -0.0036 C17 0.0274 0.0189 0.0332 0.0062 -0.0017 -0.0061 O18 0.0321 0.0238 0.0356 0.0010 0.0207 -0.0024 C19 0.0196 0.0305 0.0105 0.0044 -0.0064 -0.0051 C20 0.0208 0.0220 0.0367 0.0077 0.0063 -0.0061 C21 0.0250 0.0359 0.0159 0.0056 0.0004 -0.0022 C22 0.0471 0.0340 0.0446 -0.0203 0.0247 -0.0115 C23 0.0380 0.0315 0.0667 -0.0014 0.0319 0.0024 C24 0.0497 0.0459 0.0705 0.0126 0.0339 0.0198 C25 0.0478 0.0525 0.0310 0.0031 0.0137 0.0144 C26 0.0153 0.0299 0.0319 -0.0062 0.0023 -0.0054 C27 0.0157 0.0322 0.0284 -0.0006 0.0049 -0.0122 C28 0.0235 0.0391 0.0339 -0.0091 0.0097 -0.0115 C29 0.0383 0.0221 0.0304 -0.0031 0.0072 -0.0017 C30 0.0418 0.0326 0.0570 0.0103 0.0025 0.0060 C31 0.0220 0.0363 0.0449 0.0127 0.0178 0.0054 N32 0.0291 0.0290 0.0265 0.0043 0.0077 -0.0020 C33 0.0339 0.0293 0.0316 -0.0001 0.0082 -0.0039 C34 0.0755 0.0272 0.0670 -0.0002 -0.0277 0.0118 C35 0.0821 0.0295 0.0337 -0.0092 -0.0114 0.0074 C36 0.0644 0.0312 0.0453 0.0068 0.0120 -0.0110 _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.336(8) yes C1 . C15 . 1.394(7) yes C1 . O18 . 1.406(6) yes C2 . C3 . 1.466(8) yes C2 . C9 . 1.535(8) yes C3 . C4 . 1.343(8) yes C3 . C8 . 1.406(8) yes C4 . C5 . 1.426(8) yes C4 . H41 . 1.008 no C5 . C6 . 1.331(9) yes C5 . H51 . 0.998 no C6 . C7 . 1.394(9) yes C6 . H61 . 0.999 no C7 . C8 . 1.399(9) yes C7 . H71 . 0.986 no C8 . H81 . 0.992 no C9 . C10 . 1.383(8) yes C9 . C14 . 1.383(9) yes C10 . C11 . 1.375(9) yes C10 . H101 . 1.018 no C11 . C12 . 1.450(9) yes C11 . H111 . 0.990 no C12 . C13 . 1.36(1) yes C12 . H121 . 1.036 no C13 . C14 . 1.396(9) yes C13 . H131 . 1.027 no C14 . H141 . 1.061 no C15 . O16 . 1.445(4) yes C15 . N32 . 1.269(5) yes O16 . C17 . 1.416(7) yes C17 . O18 . 1.338(7) yes C17 . C19 . 1.333(8) yes C19 . C20 . 1.453(9) yes C19 . C26 . 1.493(8) yes C20 . C21 . 1.408(9) yes C20 . C25 . 1.392(9) yes C21 . C22 . 1.391(9) yes C21 . H211 . 0.984 no C22 . C23 . 1.403(11) yes C22 . H221 . 0.982 no C23 . C24 . 1.31(1) yes C23 . H231 . 0.999 no C24 . C25 . 1.40(1) yes C24 . H241 . 1.036 no C25 . H251 . 1.005 no C26 . C27 . 1.450(7) yes C26 . C31 . 1.397(8) yes C27 . C28 . 1.354(8) yes C27 . H271 . 1.020 no C28 . C29 . 1.429(9) yes C28 . H281 . 1.032 no C29 . C30 . 1.38(1) yes C29 . H291 . 1.035 no C30 . C31 . 1.365(9) yes C30 . H301 . 1.067 no C31 . H311 . 1.039 no N32 . C33 . 1.482(5) yes C33 . C34 . 1.457(8) yes C33 . C35 . 1.455(7) yes C33 . C36 . 1.527(6) yes C34 . H341 . 1.030 no C34 . H342 . 1.026 no C34 . H343 . 0.965 no C35 . H351 . 1.027 no C35 . H352 . 1.067 no C35 . H353 . 0.989 no C36 . H361 . 0.994 no C36 . H362 . 1.018 no C36 . H363 . 1.018 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . C15 . 131.1(5) yes C2 . C1 . O18 . 121.8(5) yes C15 . C1 . O18 . 107.0(4) yes C1 . C2 . C3 . 125.6(5) yes C1 . C2 . C9 . 116.7(5) yes C3 . C2 . C9 . 117.7(5) yes C2 . C3 . C4 . 119.4(5) yes C2 . C3 . C8 . 120.8(5) yes C4 . C3 . C8 . 119.8(5) yes C3 . C4 . C5 . 120.1(5) yes C3 . C4 . H41 . 122.273 no C5 . C4 . H41 . 117.605 no C4 . C5 . C6 . 120.6(5) yes C4 . C5 . H51 . 119.544 no C6 . C5 . H51 . 119.832 no C5 . C6 . C7 . 120.6(5) yes C5 . C6 . H61 . 117.496 no C7 . C6 . H61 . 121.898 no C6 . C7 . C8 . 119.4(5) yes C6 . C7 . H71 . 120.835 no C8 . C7 . H71 . 119.813 no C3 . C8 . C7 . 119.5(5) yes C3 . C8 . H81 . 121.706 no C7 . C8 . H81 . 118.765 no C2 . C9 . C10 . 119.6(5) yes C2 . C9 . C14 . 118.8(6) yes C10 . C9 . C14 . 121.4(5) yes C9 . C10 . C11 . 119.7(6) yes C9 . C10 . H101 . 120.781 no C11 . C10 . H101 . 119.475 no C10 . C11 . C12 . 119.7(6) yes C10 . C11 . H111 . 118.833 no C12 . C11 . H111 . 121.418 no C11 . C12 . C13 . 118.5(6) yes C11 . C12 . H121 . 120.349 no C13 . C12 . H121 . 120.879 no C12 . C13 . C14 . 121.5(6) yes C12 . C13 . H131 . 120.202 no C14 . C13 . H131 . 118.234 no C9 . C14 . C13 . 119.0(6) yes C9 . C14 . H141 . 122.068 no C13 . C14 . H141 . 118.853 no C1 . C15 . O16 . 108.4(4) yes C1 . C15 . N32 . 138.0(5) yes O16 . C15 . N32 . 113.7(5) yes C15 . O16 . C17 . 104.6(4) yes O16 . C17 . O18 . 110.4(4) yes O16 . C17 . C19 . 124.5(5) yes O18 . C17 . C19 . 125.0(5) yes C1 . O18 . C17 . 109.6(2) yes C17 . C19 . C20 . 121.0(5) yes C17 . C19 . C26 . 119.8(5) yes C20 . C19 . C26 . 119.2(5) yes C19 . C20 . C21 . 122.3(5) yes C19 . C20 . C25 . 121.7(6) yes C21 . C20 . C25 . 115.9(6) yes C20 . C21 . C22 . 121.5(5) yes C20 . C21 . H211 . 118.364 no C22 . C21 . H211 . 120.083 no C21 . C22 . C23 . 118.7(6) yes C21 . C22 . H221 . 122.599 no C23 . C22 . H221 . 118.644 no C22 . C23 . C24 . 121.2(6) yes C22 . C23 . H231 . 117.745 no C24 . C23 . H231 . 120.879 no C23 . C24 . C25 . 120.6(7) yes C23 . C24 . H241 . 117.574 no C25 . C24 . H241 . 121.848 no C20 . C25 . C24 . 122.0(7) yes C20 . C25 . H251 . 117.142 no C24 . C25 . H251 . 120.828 no C19 . C26 . C27 . 119.3(5) yes C19 . C26 . C31 . 125.7(5) yes C27 . C26 . C31 . 115.0(5) yes C26 . C27 . C28 . 122.4(5) yes C26 . C27 . H271 . 116.458 no C28 . C27 . H271 . 121.097 no C27 . C28 . C29 . 119.5(5) yes C27 . C28 . H281 . 120.617 no C29 . C28 . H281 . 119.830 no C28 . C29 . C30 . 119.2(5) yes C28 . C29 . H291 . 122.792 no C30 . C29 . H291 . 117.962 no C29 . C30 . C31 . 120.2(6) yes C29 . C30 . H301 . 119.722 no C31 . C30 . H301 . 120.058 no C26 . C31 . C30 . 123.6(6) yes C26 . C31 . H311 . 115.668 no C30 . C31 . H311 . 120.690 no C15 . N32 . C33 . 130.6(4) yes N32 . C33 . C34 . 107.7(4) yes N32 . C33 . C35 . 109.5(4) yes C34 . C33 . C35 . 119.6(5) yes N32 . C33 . C36 . 104.9(4) yes C34 . C33 . C36 . 108.2(5) yes C35 . C33 . C36 . 106.1(4) yes C33 . C34 . H341 . 109.309 no C33 . C34 . H342 . 109.311 no H341 . C34 . H342 . 105.150 no C33 . C34 . H343 . 112.729 no H341 . C34 . H343 . 109.880 no H342 . C34 . H343 . 110.181 no C33 . C35 . H351 . 113.788 no C33 . C35 . H352 . 110.931 no H351 . C35 . H352 . 102.508 no C33 . C35 . H353 . 115.180 no H351 . C35 . H353 . 108.213 no H352 . C35 . H353 . 105.137 no C33 . C36 . H361 . 112.592 no C33 . C36 . H362 . 110.438 no H361 . C36 . H362 . 108.447 no C33 . C36 . H363 . 110.049 no H361 . C36 . H363 . 108.481 no H362 . C36 . H363 . 106.631 no data_compound_2 _database_code_depnum_ccdc_archive 'CCDC 283681' _audit_creation_date 04-22-05 _audit_creation_method CRYSTALS_ver_12-03-99 _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; H atoms placed geometrically after each cycle ; _publ_section_exptl_prep ; ? ; #========================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment noref #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 9.6597(2) _cell_angle_alpha 90 _cell_length_b 14.5094(2) _cell_angle_beta 95.0930(6) _cell_length_c 17.0652(3) _cell_angle_gamma 90 _cell_volume 2382.35(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum ' C32 H27 N1 O2 ' _chemical_formula_moiety ' C32 H27 N1 O2 ' _chemical_compound_source ; ? ; _chemical_formula_weight 457.57 _cell_measurement_reflns_used 4764 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 190 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 968.000 _exptl_absorpt_coefficient_mu 0.079 # Sheldrick geometric definitions 0.98 0.99 _diffrn_measurement_device_type ; Enraf Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 190 _diffrn_reflns_number 9957 _reflns_number_total 5345 _diffrn_reflns_av_R_equivalents 0.01 # Number of reflections with Friedels Law is 5345 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5445 _diffrn_reflns_theta_min 5.138 _diffrn_reflns_theta_max 27.449 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 26.077 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _refine_diff_density_min -0.17 _refine_diff_density_max 0.36 _refine_ls_number_reflns 3927 _refine_ls_number_parameters 106 #_refine_ls_R_factor_ref 0.0413 _refine_ls_wR_factor_ref 0.0507 _refine_ls_goodness_of_fit_ref 1.0614 #_reflns_number_all 5345 _refine_ls_R_factor_all 0.0613 _refine_ls_wR_factor_all 0.0644 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 3927 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_gt 0.0507 _refine_ls_shift/su_max 0.000590 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 1.36 0.512 0.856 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 COLLECT Software, Nonius BV 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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_occupancy _atom_site_adp_type _atom_site_attached_hydrogens C1 C 0.40187(13) 0.24548(8) 0.79266(7) 0.0251 1.0000 Uani . C2 C 0.35328(13) 0.13890(9) 0.79275(7) 0.0250 1.0000 Uani . C3 C 0.34574(14) 0.14974(9) 0.70212(7) 0.0304 1.0000 Uani . N4 N 0.39437(11) 0.23662(8) 0.70665(6) 0.0276 1.0000 Uani . C5 C 0.42608(15) 0.3032(1) 0.64642(8) 0.0354 1.0000 Uani . C6 C 0.30658(17) 0.3676(1) 0.62212(9) 0.0390 1.0000 Uani . C7 C 0.17944(18) 0.31757(13) 0.5866(1) 0.0489 1.0000 Uani . O8 O 0.31235(13) 0.10052(7) 0.64590(6) 0.0437 1.0000 Uani . C9 C 0.46372(12) 0.06991(8) 0.82363(7) 0.0249 1.0000 Uani . C10 C 0.49989(15) -0.0030(1) 0.77639(8) 0.0356 1.0000 Uani . C11 C 0.59598(18) -0.06853(11) 0.8052(1) 0.0453 1.0000 Uani . C12 C 0.65698(15) -0.0629(1) 0.8813(1) 0.0390 1.0000 Uani . C13 C 0.62165(14) 0.0089(1) 0.92891(8) 0.0323 1.0000 Uani . C14 C 0.52632(14) 0.07504(9) 0.90032(8) 0.0290 1.0000 Uani . C15 C 0.21526(13) 0.11991(9) 0.82636(8) 0.0287 1.0000 Uani . C16 C 0.20051(14) 0.1362(1) 0.90577(8) 0.0350 1.0000 Uani . C17 C 0.07616(16) 0.11750(12) 0.9375(1) 0.0461 1.0000 Uani . C18 C -0.03449(17) 0.08181(13) 0.89031(13) 0.0542 1.0000 Uani . C19 C -0.02223(16) 0.06572(13) 0.81205(13) 0.0551 1.0000 Uani . C20 C 0.10217(15) 0.08520(11) 0.7792(1) 0.0410 1.0000 Uani . C21 C 0.53741(13) 0.28003(9) 0.83186(7) 0.0271 1.0000 Uani . C22 C 0.51766(15) 0.35663(9) 0.87947(8) 0.0324 1.0000 Uani . C23 C 0.36671(14) 0.38086(9) 0.88212(8) 0.0313 1.0000 Uani . C24 C 0.29465(14) 0.31514(9) 0.82103(7) 0.0283 1.0000 Uani . O25 O 0.1744(1) 0.31803(7) 0.79588(6) 0.0371 1.0000 Uani . C26 C 0.30825(15) 0.37155(9) 0.96195(8) 0.0310 1.0000 Uani . C27 C 0.17397(15) 0.40218(11) 0.97034(9) 0.0366 1.0000 Uani . C28 C 0.11749(16) 0.39538(12) 1.04210(9) 0.0429 1.0000 Uani . C29 C 0.19531(19) 0.35797(13) 1.10631(9) 0.0476 1.0000 Uani . C30 C 0.32829(19) 0.32652(12) 1.0986(1) 0.0476 1.0000 Uani . C31 C 0.38466(16) 0.33312(11) 1.02662(9) 0.0402 1.0000 Uani . C32 C 0.63160(17) 0.40198(11) 0.9167(1) 0.0449 1.0000 Uani . C33 C 0.76404(17) 0.36986(12) 0.90690(11) 0.0482 1.0000 Uani . C34 C 0.78416(15) 0.29363(11) 0.86013(9) 0.0386 1.0000 Uani . C35 C 0.67093(14) 0.2485(1) 0.82158(8) 0.0316 1.0000 Uani . H51 H 0.5093 0.3402 0.6670 0.0458 1.0000 Uiso . H52 H 0.4501 0.2681 0.5985 0.0458 1.0000 Uiso . H61 H 0.2823 0.4031 0.6698 0.0491 1.0000 Uiso . H62 H 0.3377 0.4134 0.5825 0.0491 1.0000 Uiso . H71 H 0.1023 0.3618 0.5712 0.0609 1.0000 Uiso . H72 H 0.1469 0.2722 0.6257 0.0609 1.0000 Uiso . H73 H 0.2023 0.2825 0.5384 0.0609 1.0000 Uiso . H101 H 0.4555 -0.0078 0.7206 0.0446 1.0000 Uiso . H111 H 0.6220 -0.1206 0.7701 0.0550 1.0000 Uiso . H121 H 0.7267 -0.1109 0.9016 0.0485 1.0000 Uiso . H131 H 0.6655 0.0134 0.9847 0.0401 1.0000 Uiso . H141 H 0.5017 0.1274 0.9355 0.0365 1.0000 Uiso . H161 H 0.2818 0.1615 0.9406 0.0445 1.0000 Uiso . H171 H 0.0667 0.1300 0.9950 0.0576 1.0000 Uiso . H181 H -0.1244 0.0676 0.9137 0.0680 1.0000 Uiso . H191 H -0.1037 0.0396 0.7780 0.0660 1.0000 Uiso . H201 H 0.1103 0.0747 0.7209 0.0512 1.0000 Uiso . H231 H 0.3501 0.4484 0.8704 0.0390 1.0000 Uiso . H271 H 0.1171 0.4297 0.9234 0.0475 1.0000 Uiso . H281 H 0.0198 0.4171 1.0477 0.0543 1.0000 Uiso . H291 H 0.1548 0.3542 1.1589 0.0582 1.0000 Uiso . H301 H 0.3849 0.2984 1.1456 0.0600 1.0000 Uiso . H311 H 0.4816 0.3098 1.0211 0.0502 1.0000 Uiso . H321 H 0.6176 0.4578 0.9511 0.0550 1.0000 Uiso . H331 H 0.8473 0.4020 0.9342 0.0592 1.0000 Uiso . H341 H 0.8814 0.2708 0.8536 0.0479 1.0000 Uiso . H351 H 0.6836 0.1936 0.7868 0.0391 1.0000 Uiso . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0276 0.0246 0.0233 0.0007 0.0030 0.0000 C2 0.0281 0.0244 0.0224 -0.0003 0.0008 -0.0012 C3 0.0352 0.0302 0.0252 0.0003 -0.0004 0.0024 N4 0.0328 0.0290 0.0212 0.0024 0.0027 0.0008 C5 0.0353 0.0383 0.0329 0.0108 0.0053 -0.0023 C6 0.0483 0.0322 0.0365 0.0067 0.0034 0.0022 C7 0.0425 0.0543 0.0479 0.0111 -0.0069 0.0028 O8 0.0652 0.0379 0.0263 -0.0051 -0.0049 -0.0026 C9 0.0246 0.0238 0.0266 0.0019 0.0045 -0.0020 C10 0.0397 0.0334 0.0331 -0.0064 -0.0001 0.0022 C11 0.0483 0.0384 0.0488 -0.0112 0.0026 0.0116 C12 0.0332 0.0336 0.0495 0.0031 -0.0000 0.0065 C13 0.0268 0.0359 0.0337 0.0040 0.0010 -0.0023 C14 0.0298 0.0290 0.0285 -0.0004 0.0040 -0.0002 C15 0.0259 0.0237 0.0360 0.0046 0.0003 0.0009 C16 0.0304 0.0379 0.0373 0.0062 0.0068 -0.0002 C17 0.0361 0.0509 0.0535 0.0127 0.0168 0.0046 C18 0.0274 0.0520 0.0848 0.0124 0.0148 0.0002 C19 0.0264 0.0484 0.0883 -0.0013 -0.0067 -0.0052 C20 0.0305 0.0375 0.0530 -0.0033 -0.0064 -0.0003 C21 0.0290 0.0247 0.0279 0.0022 0.0038 -0.0043 C22 0.0345 0.0267 0.0368 -0.0027 0.0073 -0.0035 C23 0.0353 0.0240 0.0352 -0.0014 0.0074 0.0011 C24 0.0325 0.0258 0.0270 0.0034 0.0056 0.0014 O25 0.0322 0.0387 0.0398 0.0019 0.0007 0.0078 C26 0.0366 0.0241 0.0326 -0.0037 0.0052 -0.0007 C27 0.0364 0.0397 0.0340 0.0003 0.0054 0.0018 C28 0.0379 0.0506 0.0413 -0.0024 0.0103 -0.0001 C29 0.0545 0.0551 0.0346 0.0007 0.0114 -0.0074 C30 0.0562 0.0493 0.0366 0.0074 -0.0003 0.0011 C31 0.0414 0.0387 0.0404 0.0003 0.0026 0.0067 C32 0.0417 0.0379 0.0555 -0.0160 0.0063 -0.0089 C33 0.0363 0.0480 0.0595 -0.0101 0.0003 -0.0138 C34 0.0280 0.0411 0.0469 0.0032 0.0041 -0.0029 C35 0.0310 0.0306 0.0337 0.0011 0.0054 -0.0008 _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.6162(17) yes C1 . N4 . 1.4687(15) yes C1 . C21 . 1.5025(17) yes C1 . C24 . 1.5549(17) yes C2 . C3 . 1.5498(17) yes C2 . C9 . 1.5225(17) yes C2 . C15 . 1.5226(18) yes C3 . N4 . 1.3451(18) yes C3 . O8 . 1.2163(16) yes N4 . C5 . 1.4628(17) yes C5 . C6 . 1.514(2) yes C5 . H51 . 1.003 no C5 . H52 . 1.008 no C6 . C7 . 1.507(2) yes C6 . H61 . 1.007 no C6 . H62 . 1.012 no C7 . H71 . 1.001 no C7 . H72 . 1.006 no C7 . H73 . 1.009 no C9 . C10 . 1.3930(19) yes C9 . C14 . 1.3941(18) yes C10 . C11 . 1.388(2) yes C10 . H101 . 1.011 no C11 . C12 . 1.380(2) yes C11 . H111 . 1.011 no C12 . C13 . 1.382(2) yes C12 . H121 . 1.008 no C13 . C14 . 1.3886(19) yes C13 . H131 . 1.010 no C14 . H141 . 1.010 no C15 . C16 . 1.395(2) yes C15 . C20 . 1.392(2) yes C16 . C17 . 1.387(2) yes C16 . H161 . 1.011 no C17 . C18 . 1.381(3) yes C17 . H171 . 1.010 no C18 . C19 . 1.371(3) yes C18 . H181 . 1.009 no C19 . C20 . 1.399(2) yes C19 . H191 . 1.011 no C20 . H201 . 1.017 no C21 . C22 . 1.3998(19) yes C21 . C35 . 1.3941(19) yes C22 . C23 . 1.5044(19) yes C22 . C32 . 1.387(2) yes C23 . C24 . 1.5336(19) yes C23 . C26 . 1.5264(19) yes C23 . H231 . 1.010 no C24 . O25 . 1.2029(16) yes C26 . C27 . 1.390(2) yes C26 . C31 . 1.389(2) yes C27 . C28 . 1.388(2) yes C27 . H271 . 1.012 no C28 . C29 . 1.384(2) yes C28 . H281 . 1.008 no C29 . C30 . 1.380(3) yes C29 . H291 . 1.012 no C30 . C31 . 1.391(2) yes C30 . H301 . 1.015 no C31 . H311 . 1.008 no C32 . C33 . 1.386(2) yes C32 . H321 . 1.016 no C33 . C34 . 1.388(2) yes C33 . H331 . 1.007 no C34 . C35 . 1.389(2) yes C34 . H341 . 1.011 no C35 . H351 . 1.007 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . N4 . 85.91(9) yes C2 . C1 . C21 . 124.1(1) yes N4 . C1 . C21 . 116.0(1) yes C2 . C1 . C24 . 114.8(1) yes N4 . C1 . C24 . 113.1(1) yes C21 . C1 . C24 . 102.9(1) yes C1 . C2 . C3 . 83.68(9) yes C1 . C2 . C9 . 115.8(1) yes C3 . C2 . C9 . 112.4(1) yes C1 . C2 . C15 . 115.9(1) yes C3 . C2 . C15 . 115.4(1) yes C9 . C2 . C15 . 111.1(1) yes C2 . C3 . N4 . 93.0(1) yes C2 . C3 . O8 . 135.49(13) yes N4 . C3 . O8 . 131.48(13) yes C1 . N4 . C3 . 97.2(1) yes C1 . N4 . C5 . 130.50(11) yes C3 . N4 . C5 . 132.27(11) yes N4 . C5 . C6 . 113.46(12) yes N4 . C5 . H51 . 108.591 no C6 . C5 . H51 . 109.473 no N4 . C5 . H52 . 108.238 no C6 . C5 . H52 . 108.386 no H51 . C5 . H52 . 108.579 no C5 . C6 . C7 . 112.74(13) yes C5 . C6 . H61 . 108.674 no C7 . C6 . H61 . 109.320 no C5 . C6 . H62 . 108.851 no C7 . C6 . H62 . 109.134 no H61 . C6 . H62 . 108.006 no C6 . C7 . H71 . 110.953 no C6 . C7 . H72 . 109.931 no H71 . C7 . H72 . 108.928 no C6 . C7 . H73 . 109.965 no H71 . C7 . H73 . 108.713 no H72 . C7 . H73 . 108.294 no C2 . C9 . C10 . 120.18(11) yes C2 . C9 . C14 . 121.47(11) yes C10 . C9 . C14 . 118.28(12) yes C9 . C10 . C11 . 120.60(13) yes C9 . C10 . H101 . 119.396 no C11 . C10 . H101 . 120.006 no C10 . C11 . C12 . 120.64(14) yes C10 . C11 . H111 . 119.718 no C12 . C11 . H111 . 119.638 no C11 . C12 . C13 . 119.35(13) yes C11 . C12 . H121 . 119.965 no C13 . C12 . H121 . 120.683 no C12 . C13 . C14 . 120.35(13) yes C12 . C13 . H131 . 119.943 no C14 . C13 . H131 . 119.708 no C9 . C14 . C13 . 120.78(12) yes C9 . C14 . H141 . 119.568 no C13 . C14 . H141 . 119.653 no C2 . C15 . C16 . 120.24(11) yes C2 . C15 . C20 . 121.06(13) yes C16 . C15 . C20 . 118.70(13) yes C15 . C16 . C17 . 120.83(14) yes C15 . C16 . H161 . 119.486 no C17 . C16 . H161 . 119.685 no C16 . C17 . C18 . 119.87(16) yes C16 . C17 . H171 . 120.028 no C18 . C17 . H171 . 120.102 no C17 . C18 . C19 . 120.17(15) yes C17 . C18 . H181 . 119.631 no C19 . C18 . H181 . 120.200 no C18 . C19 . C20 . 120.49(15) yes C18 . C19 . H191 . 119.635 no C20 . C19 . H191 . 119.873 no C15 . C20 . C19 . 119.93(16) yes C15 . C20 . H201 . 119.697 no C19 . C20 . H201 . 120.368 no C1 . C21 . C22 . 111.41(11) yes C1 . C21 . C35 . 127.86(12) yes C22 . C21 . C35 . 120.59(12) yes C21 . C22 . C23 . 112.66(12) yes C21 . C22 . C32 . 119.94(13) yes C23 . C22 . C32 . 127.39(13) yes C22 . C23 . C24 . 102.5(1) yes C22 . C23 . C26 . 116.26(12) yes C24 . C23 . C26 . 111.72(11) yes C22 . C23 . H231 . 110.976 no C24 . C23 . H231 . 114.441 no C26 . C23 . H231 . 101.434 no C1 . C24 . C23 . 109.9(1) yes C1 . C24 . O25 . 124.09(12) yes C23 . C24 . O25 . 125.92(12) yes C23 . C26 . C27 . 119.08(12) yes C23 . C26 . C31 . 122.15(13) yes C27 . C26 . C31 . 118.77(13) yes C26 . C27 . C28 . 120.77(14) yes C26 . C27 . H271 . 119.374 no C28 . C27 . H271 . 119.859 no C27 . C28 . C29 . 119.89(15) yes C27 . C28 . H281 . 120.369 no C29 . C28 . H281 . 119.742 no C28 . C29 . C30 . 119.94(15) yes C28 . C29 . H291 . 119.896 no C30 . C29 . H291 . 120.157 no C29 . C30 . C31 . 120.12(15) yes C29 . C30 . H301 . 119.914 no C31 . C30 . H301 . 119.962 no C26 . C31 . C30 . 120.50(14) yes C26 . C31 . H311 . 119.545 no C30 . C31 . H311 . 119.954 no C22 . C32 . C33 . 119.26(14) yes C22 . C32 . H321 . 120.082 no C33 . C32 . H321 . 120.654 no C32 . C33 . C34 . 121.03(14) yes C32 . C33 . H331 . 119.732 no C34 . C33 . H331 . 119.240 no C33 . C34 . C35 . 120.22(14) yes C33 . C34 . H341 . 120.211 no C35 . C34 . H341 . 119.564 no C21 . C35 . C34 . 118.95(13) yes C21 . C35 . H351 . 119.727 no C34 . C35 . H351 . 121.321 no data_compound_3 _database_code_depnum_ccdc_archive 'CCDC 283682' _audit_creation_date 04-21-05 _audit_creation_method CRYSTALS_ver_12-03-99 _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; H atoms placed geometrically after each cycle ; _publ_section_exptl_prep ; ? ; #========================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment noref #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 11.6080(3) _cell_angle_alpha 90 _cell_length_b 17.2569(5) _cell_angle_beta 103.7016(17) _cell_length_c 17.9855(5) _cell_angle_gamma 90 _cell_volume 3500.29(17) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum ' C46 H37 N1 O3 ' _chemical_formula_moiety ' C46 H37 N1 O3 ' _chemical_compound_source ; ? ; _chemical_formula_weight 651.80 _cell_measurement_reflns_used 7350 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.16 _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1376.000 _exptl_absorpt_coefficient_mu 0.076 # Sheldrick geometric definitions 0.99 0.99 _diffrn_measurement_device_type ; Enraf Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 13093 _reflns_number_total 7987 _diffrn_reflns_av_R_equivalents 0.02 # Number of reflections with Friedels Law is 7987 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 8004 _diffrn_reflns_theta_min 2.157 _diffrn_reflns_theta_max 27.474 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.474 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min -15 _reflns_limit_h_max 14 _reflns_limit_k_min 0 _reflns_limit_k_max 22 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _refine_diff_density_min -0.30 _refine_diff_density_max 0.26 _refine_ls_number_reflns 4007 _refine_ls_number_parameters 151 #_refine_ls_R_factor_ref 0.0463 _refine_ls_wR_factor_ref 0.0528 _refine_ls_goodness_of_fit_ref 0.9006 #_reflns_number_all 7987 _refine_ls_R_factor_all 0.1193 _refine_ls_wR_factor_all 0.1191 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 4007 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_gt 0.0528 _refine_ls_shift/su_max 0.000301 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 0.731 0.474 0.373 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 COLLECT Software, Nonius BV 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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_occupancy _atom_site_adp_type _atom_site_attached_hydrogens C1 C 0.54785(18) 0.22332(12) 0.16512(11) 0.0260 1.0000 Uani . C2 C 0.42414(18) 0.24033(12) 0.10288(12) 0.0293 1.0000 Uani . C3 C 0.46932(19) 0.32510(12) 0.11185(13) 0.0335 1.0000 Uani . N4 N 0.55755(15) 0.3078(1) 0.1738(1) 0.0306 1.0000 Uani . C5 C 0.64438(19) 0.35679(13) 0.22502(13) 0.0341 1.0000 Uani . C6 C 0.6041(2) 0.38109(14) 0.29502(13) 0.0393 1.0000 Uani . C7 C 0.6945(3) 0.43144(18) 0.34809(16) 0.0594 1.0000 Uani . O8 O 0.44058(15) 0.38530(9) 0.0780(1) 0.0471 1.0000 Uani . C9 C 0.40204(17) 0.20454(13) 0.02416(12) 0.0293 1.0000 Uani . C10 C 0.33998(19) 0.24796(14) -0.03762(13) 0.0354 1.0000 Uani . C11 C 0.3096(2) 0.21548(16) -0.11054(13) 0.0427 1.0000 Uani . C12 C 0.3404(2) 0.13996(17) -0.12216(14) 0.0469 1.0000 Uani . C13 C 0.4024(2) 0.09665(15) -0.06080(15) 0.0443 1.0000 Uani . C14 C 0.43219(19) 0.12827(13) 0.01207(13) 0.0355 1.0000 Uani . C15 C 0.31550(18) 0.23041(13) 0.13619(12) 0.0330 1.0000 Uani . C16 C 0.2735(2) 0.15629(15) 0.14457(15) 0.0428 1.0000 Uani . C17 C 0.1766(2) 0.14522(17) 0.17607(16) 0.0498 1.0000 Uani . C18 C 0.1188(2) 0.20778(18) 0.19848(14) 0.0489 1.0000 Uani . C19 C 0.1579(2) 0.28107(18) 0.18880(13) 0.0494 1.0000 Uani . C20 C 0.2563(2) 0.29302(15) 0.15821(13) 0.0395 1.0000 Uani . C21 C 0.64397(17) 0.18829(12) 0.13247(11) 0.0259 1.0000 Uani . C22 C 0.69064(17) 0.12337(12) 0.16759(11) 0.0272 1.0000 Uani . C23 C 0.62924(17) 0.10902(12) 0.23038(11) 0.0273 1.0000 Uani . C24 C 0.55104(18) 0.17103(12) 0.23264(11) 0.0277 1.0000 Uani . C25 C 0.48994(19) 0.17547(13) 0.28968(13) 0.0348 1.0000 Uani . C26 C 0.5051(2) 0.11614(15) 0.34437(13) 0.0394 1.0000 Uani . C27 C 0.5766(2) 0.05305(14) 0.33964(13) 0.0386 1.0000 Uani . C28 C 0.63939(19) 0.04869(12) 0.28238(12) 0.0321 1.0000 Uani . C29 C 0.78471(18) 0.07461(12) 0.14945(12) 0.0283 1.0000 Uani . C30 C 0.87066(19) 0.04032(13) 0.20786(13) 0.0351 1.0000 Uani . C31 C 0.9579(2) -0.00691(14) 0.19038(15) 0.0422 1.0000 Uani . C32 C 0.9604(2) -0.01937(14) 0.11456(16) 0.0444 1.0000 Uani . C33 C 0.8765(2) 0.01514(15) 0.05650(15) 0.0432 1.0000 Uani . C34 C 0.7892(2) 0.06227(13) 0.07358(13) 0.0351 1.0000 Uani . O35 O 0.67235(12) 0.22625(8) 0.07100(7) 0.0279 1.0000 Uani . C36 C 0.77287(17) 0.27161(12) 0.08701(12) 0.0271 1.0000 Uani . C37 C 0.77836(17) 0.32093(12) 0.01824(11) 0.0280 1.0000 Uani . C38 C 0.85283(17) 0.28278(12) -0.03112(11) 0.0266 1.0000 Uani . C39 C 0.82329(19) 0.29694(13) -0.10934(12) 0.0313 1.0000 Uani . C40 C 0.8923(2) 0.26746(14) -0.15635(12) 0.0365 1.0000 Uani . C41 C 0.9919(2) 0.22388(14) -0.12511(13) 0.0377 1.0000 Uani . C42 C 1.0217(2) 0.20912(14) -0.04711(13) 0.0391 1.0000 Uani . C43 C 0.95181(19) 0.23793(13) -0.00032(12) 0.0334 1.0000 Uani . C44 C 0.8217(2) 0.40196(12) 0.04568(12) 0.0311 1.0000 Uani . C45 C 0.9415(2) 0.42117(14) 0.06441(13) 0.0380 1.0000 Uani . C46 C 0.9776(3) 0.49548(15) 0.09044(14) 0.0486 1.0000 Uani . C47 C 0.8957(3) 0.54986(16) 0.09882(17) 0.0588 1.0000 Uani . C48 C 0.7769(3) 0.53114(17) 0.0811(2) 0.0672 1.0000 Uani . C49 C 0.7389(2) 0.45725(15) 0.05424(16) 0.0493 1.0000 Uani . O50 O 0.84293(13) 0.2708(1) 0.14779(8) 0.0362 1.0000 Uani . H51 H 0.6610 0.4043 0.1970 0.0422 1.0000 Uiso . H52 H 0.7220 0.3268 0.2417 0.0422 1.0000 Uiso . H61 H 0.5279 0.4105 0.2796 0.0445 1.0000 Uiso . H62 H 0.5896 0.3332 0.3245 0.0445 1.0000 Uiso . H71 H 0.6687 0.4474 0.3953 0.0672 1.0000 Uiso . H72 H 0.7120 0.4799 0.3211 0.0672 1.0000 Uiso . H73 H 0.7737 0.4026 0.3660 0.0672 1.0000 Uiso . H101 H 0.3182 0.3036 -0.0276 0.0391 1.0000 Uiso . H111 H 0.2650 0.2482 -0.1549 0.0508 1.0000 Uiso . H121 H 0.3183 0.1162 -0.1744 0.0559 1.0000 Uiso . H131 H 0.4286 0.0411 -0.0679 0.0497 1.0000 Uiso . H141 H 0.4764 0.0961 0.0579 0.0396 1.0000 Uiso . H161 H 0.3130 0.1101 0.1262 0.0491 1.0000 Uiso . H171 H 0.1474 0.0900 0.1830 0.0569 1.0000 Uiso . H181 H 0.0488 0.2002 0.2221 0.0539 1.0000 Uiso . H191 H 0.1140 0.3278 0.2041 0.0548 1.0000 Uiso . H201 H 0.2836 0.3480 0.1505 0.0434 1.0000 Uiso . H251 H 0.4365 0.2210 0.2929 0.0404 1.0000 Uiso . H261 H 0.4655 0.1196 0.3891 0.0445 1.0000 Uiso . H271 H 0.5834 0.0091 0.3782 0.0440 1.0000 Uiso . H281 H 0.6933 0.0024 0.2800 0.0367 1.0000 Uiso . H301 H 0.8687 0.0500 0.2640 0.0390 1.0000 Uiso . H311 H 1.0201 -0.0317 0.2343 0.0476 1.0000 Uiso . H321 H 1.0249 -0.0537 0.1026 0.0515 1.0000 Uiso . H331 H 0.8783 0.0055 0.0005 0.0532 1.0000 Uiso . H341 H 0.7272 0.0880 0.0303 0.0423 1.0000 Uiso . H371 H 0.6952 0.3248 -0.0168 0.0324 1.0000 Uiso . H391 H 0.7494 0.3296 -0.1330 0.0358 1.0000 Uiso . H401 H 0.8681 0.2779 -0.2142 0.0420 1.0000 Uiso . H411 H 1.0418 0.2028 -0.1599 0.0440 1.0000 Uiso . H421 H 1.0956 0.1772 -0.0242 0.0450 1.0000 Uiso . H431 H 0.9723 0.2265 0.0567 0.0370 1.0000 Uiso . H451 H 1.0026 0.3799 0.0592 0.0439 1.0000 Uiso . H461 H 1.0679 0.5086 0.1045 0.0580 1.0000 Uiso . H471 H 0.9230 0.6043 0.1185 0.0663 1.0000 Uiso . H481 H 0.7166 0.5719 0.0876 0.0820 1.0000 Uiso . H491 H 0.6496 0.4438 0.0389 0.0593 1.0000 Uiso . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0277 0.0241 0.0266 -0.0000 0.0072 -0.0003 C2 0.0300 0.0254 0.0307 0.0015 0.0034 0.0024 C3 0.0360 0.0262 0.0376 -0.0011 0.0071 0.0019 N4 0.0340 0.0262 0.0299 -0.0047 0.0042 -0.0018 C5 0.0331 0.0322 0.0386 -0.0084 0.0117 -0.0060 C6 0.0396 0.0440 0.0336 -0.0078 0.0071 -0.0027 C7 0.0691 0.0623 0.0460 -0.0227 0.0118 -0.0160 O8 0.0560 0.0241 0.0537 0.0030 -0.0017 0.0013 C9 0.0247 0.0307 0.0317 -0.0016 0.0051 -0.0060 C10 0.0308 0.0393 0.0361 0.0046 0.0079 -0.0037 C11 0.0358 0.0624 0.0295 0.0053 0.0068 -0.0072 C12 0.0374 0.0700 0.0346 -0.0151 0.0111 -0.0143 C13 0.0366 0.0473 0.0485 -0.0185 0.0088 -0.0083 C14 0.0335 0.0299 0.0400 -0.0048 0.0026 -0.0036 C15 0.0264 0.0408 0.0292 -0.0036 0.0016 0.0029 C16 0.0325 0.0449 0.0535 -0.0065 0.0154 -0.0039 C17 0.0348 0.0648 0.0506 -0.0039 0.0117 -0.0111 C18 0.0290 0.0850 0.0321 0.0003 0.0061 0.0051 C19 0.0413 0.0738 0.0312 -0.0041 0.0046 0.0249 C20 0.0397 0.0475 0.0290 -0.0021 0.0035 0.0136 C21 0.0279 0.0274 0.0222 0.0007 0.0055 -0.0052 C22 0.0273 0.0273 0.0268 -0.0023 0.0059 -0.0029 C23 0.0270 0.0283 0.0259 -0.0013 0.0050 -0.0048 C24 0.0274 0.0282 0.0271 -0.0018 0.0059 -0.0046 C25 0.0325 0.0392 0.0350 -0.0022 0.0127 -0.0020 C26 0.0399 0.0465 0.0361 0.0015 0.0178 -0.0094 C27 0.0449 0.0362 0.0357 0.0074 0.0118 -0.0085 C28 0.0356 0.0292 0.0304 0.0014 0.0052 -0.0057 C29 0.0274 0.0246 0.0335 -0.0005 0.0085 -0.0026 C30 0.0327 0.0329 0.0389 0.0016 0.0071 0.0004 C31 0.0318 0.0369 0.0561 0.0048 0.0072 0.0046 C32 0.0354 0.0377 0.0660 -0.0064 0.0236 0.0029 C33 0.0444 0.0442 0.0467 -0.0093 0.0218 -0.0012 C34 0.0382 0.0343 0.0351 -0.0004 0.0135 0.0008 O35 0.0291 0.0316 0.0226 0.0024 0.0051 -0.0052 C36 0.0263 0.0275 0.0296 0.0013 0.0108 0.0043 C37 0.0272 0.0324 0.0239 0.0046 0.0048 0.0011 C38 0.0273 0.0273 0.0249 -0.0014 0.0056 -0.0053 C39 0.0329 0.0337 0.0271 0.0010 0.0064 -0.0013 C40 0.0434 0.0422 0.0253 -0.0004 0.0113 -0.0072 C41 0.0395 0.0387 0.0390 -0.0079 0.0176 -0.0030 C42 0.0361 0.0413 0.0393 -0.0039 0.0079 0.0066 C43 0.0344 0.0377 0.0267 0.0011 0.0048 0.0028 C44 0.0415 0.0303 0.0238 0.0036 0.0124 0.0019 C45 0.0421 0.0390 0.0335 -0.0016 0.0105 -0.0051 C46 0.0604 0.0466 0.0369 -0.0046 0.0079 -0.0156 C47 0.0886 0.0346 0.0530 -0.0028 0.0159 -0.0074 C48 0.0816 0.0359 0.0865 -0.0032 0.0243 0.0153 C49 0.0523 0.0389 0.0581 0.0032 0.0159 0.0108 O50 0.0303 0.0491 0.0277 0.0079 0.0036 -0.0063 _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.625(3) yes C1 . N4 . 1.468(3) yes C1 . C21 . 1.505(3) yes C1 . C24 . 1.506(3) yes C2 . C3 . 1.550(3) yes C2 . C9 . 1.510(3) yes C2 . C15 . 1.528(3) yes C3 . N4 . 1.356(3) yes C3 . O8 . 1.211(3) yes N4 . C5 . 1.462(3) yes C5 . C6 . 1.503(3) yes C5 . H51 . 1.004 no C5 . H52 . 1.021 no C6 . C7 . 1.514(4) yes C6 . H61 . 0.999 no C6 . H62 . 1.017 no C7 . H71 . 1.004 no C7 . H72 . 1.011 no C7 . H73 . 1.027 no C9 . C10 . 1.391(3) yes C9 . C14 . 1.392(3) yes C10 . C11 . 1.393(3) yes C10 . H101 . 1.020 no C11 . C12 . 1.380(4) yes C11 . H111 . 1.014 no C12 . C13 . 1.385(4) yes C12 . H121 . 1.002 no C13 . C14 . 1.386(3) yes C13 . H131 . 1.022 no C14 . H141 . 1.025 no C15 . C16 . 1.390(3) yes C15 . C20 . 1.388(3) yes C16 . C17 . 1.388(3) yes C16 . H161 . 1.013 no C17 . C18 . 1.381(4) yes C17 . H171 . 1.029 no C18 . C19 . 1.369(4) yes C18 . H181 . 1.010 no C19 . C20 . 1.395(3) yes C19 . H191 . 1.026 no C20 . H201 . 1.020 no C21 . C22 . 1.336(3) yes C21 . O35 . 1.390(2) yes C22 . C23 . 1.492(3) yes C22 . C29 . 1.475(3) yes C23 . C24 . 1.410(3) yes C23 . C28 . 1.386(3) yes C24 . C25 . 1.381(3) yes C25 . C26 . 1.402(3) yes C25 . H251 . 1.011 no C26 . C27 . 1.384(3) yes C26 . H261 . 1.019 no C27 . C28 . 1.397(3) yes C27 . H271 . 1.018 no C28 . H281 . 1.022 no C29 . C30 . 1.397(3) yes C29 . C34 . 1.394(3) yes C30 . C31 . 1.392(3) yes C30 . H301 . 1.030 no C31 . C32 . 1.388(4) yes C31 . H311 . 1.028 no C32 . C33 . 1.383(4) yes C32 . H321 . 1.017 no C33 . C34 . 1.389(3) yes C33 . H331 . 1.025 no C34 . H341 . 1.027 no O35 . C36 . 1.378(2) yes C36 . C37 . 1.515(3) yes C36 . O50 . 1.198(2) yes C37 . C38 . 1.527(3) yes C37 . C44 . 1.528(3) yes C37 . H371 . 1.022 no C38 . C39 . 1.388(3) yes C38 . C43 . 1.387(3) yes C39 . C40 . 1.392(3) yes C39 . H391 . 1.031 no C40 . C41 . 1.382(3) yes C40 . H401 . 1.027 no C41 . C42 . 1.387(3) yes C41 . H411 . 1.016 no C42 . C43 . 1.392(3) yes C42 . H421 . 1.021 no C43 . H431 . 1.016 no C44 . C45 . 1.391(3) yes C44 . C49 . 1.388(3) yes C45 . C46 . 1.395(3) yes C45 . H451 . 1.025 no C46 . C47 . 1.370(4) yes C46 . H461 . 1.043 no C47 . C48 . 1.377(5) yes C47 . H471 . 1.027 no C48 . C49 . 1.398(4) yes C48 . H481 . 1.019 no C49 . H491 . 1.034 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . N4 . 85.80(14) yes C2 . C1 . C21 . 114.81(16) yes N4 . C1 . C21 . 113.28(16) yes C2 . C1 . C24 . 120.84(16) yes N4 . C1 . C24 . 121.51(17) yes C21 . C1 . C24 . 101.24(16) yes C1 . C2 . C3 . 82.92(15) yes C1 . C2 . C9 . 119.89(17) yes C3 . C2 . C9 . 117.51(18) yes C1 . C2 . C15 . 112.73(16) yes C3 . C2 . C15 . 110.81(17) yes C9 . C2 . C15 . 110.43(17) yes C2 . C3 . N4 . 92.82(16) yes C2 . C3 . O8 . 135.4(2) yes N4 . C3 . O8 . 131.8(2) yes C1 . N4 . C3 . 96.14(16) yes C1 . N4 . C5 . 131.68(17) yes C3 . N4 . C5 . 131.63(19) yes N4 . C5 . C6 . 112.58(17) yes N4 . C5 . H51 . 109.974 no C6 . C5 . H51 . 109.078 no N4 . C5 . H52 . 108.746 no C6 . C5 . H52 . 108.814 no H51 . C5 . H52 . 107.512 no C5 . C6 . C7 . 112.4(2) yes C5 . C6 . H61 . 109.877 no C7 . C6 . H61 . 108.617 no C5 . C6 . H62 . 109.472 no C7 . C6 . H62 . 108.219 no H61 . C6 . H62 . 108.131 no C6 . C7 . H71 . 112.911 no C6 . C7 . H72 . 111.044 no H71 . C7 . H72 . 108.286 no C6 . C7 . H73 . 110.764 no H71 . C7 . H73 . 107.043 no H72 . C7 . H73 . 106.501 no C2 . C9 . C10 . 118.0(2) yes C2 . C9 . C14 . 122.68(19) yes C10 . C9 . C14 . 119.1(2) yes C9 . C10 . C11 . 120.2(2) yes C9 . C10 . H101 . 117.990 no C11 . C10 . H101 . 121.806 no C10 . C11 . C12 . 120.4(2) yes C10 . C11 . H111 . 118.972 no C12 . C11 . H111 . 120.645 no C11 . C12 . C13 . 119.5(2) yes C11 . C12 . H121 . 120.701 no C13 . C12 . H121 . 119.751 no C12 . C13 . C14 . 120.5(2) yes C12 . C13 . H131 . 121.349 no C14 . C13 . H131 . 118.164 no C9 . C14 . C13 . 120.3(2) yes C9 . C14 . H141 . 118.862 no C13 . C14 . H141 . 120.848 no C2 . C15 . C16 . 119.26(19) yes C2 . C15 . C20 . 122.4(2) yes C16 . C15 . C20 . 118.4(2) yes C15 . C16 . C17 . 120.7(2) yes C15 . C16 . H161 . 119.487 no C17 . C16 . H161 . 119.815 no C16 . C17 . C18 . 120.6(3) yes C16 . C17 . H171 . 119.897 no C18 . C17 . H171 . 119.524 no C17 . C18 . C19 . 119.1(2) yes C17 . C18 . H181 . 121.134 no C19 . C18 . H181 . 119.771 no C18 . C19 . C20 . 120.9(2) yes C18 . C19 . H191 . 119.425 no C20 . C19 . H191 . 119.644 no C15 . C20 . C19 . 120.3(2) yes C15 . C20 . H201 . 119.634 no C19 . C20 . H201 . 120.040 no C1 . C21 . C22 . 114.04(17) yes C1 . C21 . O35 . 117.27(17) yes C22 . C21 . O35 . 128.69(18) yes C21 . C22 . C23 . 106.50(18) yes C21 . C22 . C29 . 127.75(18) yes C23 . C22 . C29 . 125.75(18) yes C22 . C23 . C24 . 108.79(17) yes C22 . C23 . C28 . 131.00(19) yes C24 . C23 . C28 . 120.20(18) yes C1 . C24 . C23 . 108.93(17) yes C1 . C24 . C25 . 130.3(2) yes C23 . C24 . C25 . 120.74(19) yes C24 . C25 . C26 . 118.7(2) yes C24 . C25 . H251 . 121.004 no C26 . C25 . H251 . 120.317 no C25 . C26 . C27 . 120.6(2) yes C25 . C26 . H261 . 120.463 no C27 . C26 . H261 . 118.932 no C26 . C27 . C28 . 120.9(2) yes C26 . C27 . H271 . 119.627 no C28 . C27 . H271 . 119.513 no C23 . C28 . C27 . 118.8(2) yes C23 . C28 . H281 . 120.946 no C27 . C28 . H281 . 120.283 no C22 . C29 . C30 . 120.62(19) yes C22 . C29 . C34 . 120.32(19) yes C30 . C29 . C34 . 119.06(19) yes C29 . C30 . C31 . 120.4(2) yes C29 . C30 . H301 . 119.432 no C31 . C30 . H301 . 120.177 no C30 . C31 . C32 . 119.9(2) yes C30 . C31 . H311 . 119.071 no C32 . C31 . H311 . 121.036 no C31 . C32 . C33 . 120.0(2) yes C31 . C32 . H321 . 119.103 no C33 . C32 . H321 . 120.870 no C32 . C33 . C34 . 120.4(2) yes C32 . C33 . H331 . 119.786 no C34 . C33 . H331 . 119.858 no C29 . C34 . C33 . 120.3(2) yes C29 . C34 . H341 . 119.586 no C33 . C34 . H341 . 120.147 no C21 . O35 . C36 . 116.74(15) yes O35 . C36 . C37 . 110.23(16) yes O35 . C36 . O50 . 122.86(18) yes C37 . C36 . O50 . 126.91(19) yes C36 . C37 . C38 . 111.81(17) yes C36 . C37 . C44 . 108.96(16) yes C38 . C37 . C44 . 113.19(16) yes C36 . C37 . H371 . 108.917 no C38 . C37 . H371 . 104.508 no C44 . C37 . H371 . 109.301 no C37 . C38 . C39 . 118.38(18) yes C37 . C38 . C43 . 122.52(18) yes C39 . C38 . C43 . 119.02(19) yes C38 . C39 . C40 . 120.8(2) yes C38 . C39 . H391 . 119.715 no C40 . C39 . H391 . 119.504 no C39 . C40 . C41 . 119.9(2) yes C39 . C40 . H401 . 119.503 no C41 . C40 . H401 . 120.605 no C40 . C41 . C42 . 119.7(2) yes C40 . C41 . H411 . 119.294 no C42 . C41 . H411 . 120.982 no C41 . C42 . C43 . 120.3(2) yes C41 . C42 . H421 . 119.483 no C43 . C42 . H421 . 120.218 no C38 . C43 . C42 . 120.3(2) yes C38 . C43 . H431 . 119.053 no C42 . C43 . H431 . 120.673 no C37 . C44 . C45 . 122.01(19) yes C37 . C44 . C49 . 118.8(2) yes C45 . C44 . C49 . 119.2(2) yes C44 . C45 . C46 . 120.3(2) yes C44 . C45 . H451 . 119.052 no C46 . C45 . H451 . 120.690 no C45 . C46 . C47 . 120.3(3) yes C45 . C46 . H461 . 119.064 no C47 . C46 . H461 . 120.577 no C46 . C47 . C48 . 119.8(3) yes C46 . C47 . H471 . 119.912 no C48 . C47 . H471 . 120.287 no C47 . C48 . C49 . 120.7(3) yes C47 . C48 . H481 . 119.261 no C49 . C48 . H481 . 120.033 no C44 . C49 . C48 . 119.7(3) yes C44 . C49 . H491 . 119.548 no C48 . C49 . H491 . 120.737 no data_compound_5 _database_code_depnum_ccdc_archive 'CCDC 283683' _audit_creation_date 04-19-05 _audit_creation_method CRYSTALS_ver_12-03-99 _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; H atoms placed geometrically after each cycle ; _publ_section_exptl_prep ; ? ; #========================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment noref #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 17.7513(3) _cell_angle_alpha 90 _cell_length_b 5.9105(1) _cell_angle_beta 96.6068(9) _cell_length_c 23.5922(5) _cell_angle_gamma 90 _cell_volume 2458.83(8) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum ' C32 H27 N1 O2 ' _chemical_formula_moiety ' C32 H27 N1 O2 ' _chemical_compound_source ; ? ; _chemical_formula_weight 457.57 _cell_measurement_reflns_used 4999 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27 _cell_measurement_temperature 190 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' yellow ' _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.30 _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 968.000 _exptl_absorpt_coefficient_mu 0.076 # Sheldrick geometric definitions 0.98 0.99 _diffrn_measurement_device_type ; Enraf Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 190 _diffrn_reflns_number 10132 _reflns_number_total 5496 _diffrn_reflns_av_R_equivalents 0.01 # Number of reflections with Friedels Law is 5496 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5643 _diffrn_reflns_theta_min 1.155 _diffrn_reflns_theta_max 27.503 _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 20.765 _diffrn_measured_fraction_theta_full 0.979 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _reflns_limit_h_min -22 _reflns_limit_h_max 22 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 30 _refine_diff_density_min -0.19 _refine_diff_density_max 0.22 _refine_ls_number_reflns 3590 _refine_ls_number_parameters 316 #_refine_ls_R_factor_ref 0.0395 _refine_ls_wR_factor_ref 0.0460 _refine_ls_goodness_of_fit_ref 1.0569 #_reflns_number_all 5496 _refine_ls_R_factor_all 0.0723 _refine_ls_wR_factor_all 0.0696 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 3590 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_gt 0.0460 _refine_ls_shift/su_max 0.000436 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 0.994 0.457 0.550 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 COLLECT Software, Nonius BV 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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_occupancy _atom_site_adp_type _atom_site_attached_hydrogens C1 C 0.78959(8) -0.2028(2) 0.11351(6) 0.0282 1.0000 Uani . C2 C 0.82431(8) -0.0993(2) 0.16004(6) 0.0275 1.0000 Uani . C3 C 0.89252(8) 0.0441(2) 0.15544(6) 0.0287 1.0000 Uani . C4 C 0.96183(8) -0.0164(3) 0.18514(6) 0.0352 1.0000 Uani . C5 C 1.02471(9) 0.1221(3) 0.18341(7) 0.0432 1.0000 Uani . C6 C 1.01860(9) 0.3215(3) 0.15257(7) 0.0461 1.0000 Uani . C7 C 0.9502(1) 0.3822(3) 0.12312(8) 0.0465 1.0000 Uani . C8 C 0.88738(9) 0.2437(3) 0.12432(7) 0.0384 1.0000 Uani . C9 C 0.79636(8) -0.1149(2) 0.21716(6) 0.0293 1.0000 Uani . C10 C 0.80970(9) 0.0648(3) 0.25534(6) 0.0358 1.0000 Uani . C11 C 0.7838(1) 0.0574(3) 0.30890(7) 0.0444 1.0000 Uani . C12 C 0.7450(1) -0.1286(3) 0.32515(7) 0.0474 1.0000 Uani . C13 C 0.73200(11) -0.3085(3) 0.28801(7) 0.0485 1.0000 Uani . C14 C 0.7572(1) -0.3035(3) 0.23450(6) 0.0409 1.0000 Uani . C15 C 0.80956(8) -0.2259(2) 0.05515(6) 0.0299 1.0000 Uani . O16 O 0.75670(6) -0.38159(18) 0.02799(4) 0.0332 1.0000 Uani . C17 C 0.70774(8) -0.4446(2) 0.06571(6) 0.0288 1.0000 Uani . O18 O 0.72337(5) -0.32575(17) 0.11554(4) 0.0317 1.0000 Uani . C19 C 0.65400(8) -0.6024(2) 0.05897(6) 0.0279 1.0000 Uani . C20 C 0.61063(8) -0.6361(2) 0.10941(6) 0.0285 1.0000 Uani . C21 C 0.54824(9) -0.5019(3) 0.11632(6) 0.0342 1.0000 Uani . C22 C 0.5104(1) -0.5256(3) 0.16446(7) 0.0422 1.0000 Uani . C23 C 0.5343(1) -0.6839(3) 0.20578(7) 0.0455 1.0000 Uani . C24 C 0.59553(11) -0.8192(3) 0.19899(7) 0.0497 1.0000 Uani . C25 C 0.63356(9) -0.7958(3) 0.15099(7) 0.0431 1.0000 Uani . C26 C 0.63820(8) -0.7445(2) 0.00739(6) 0.0288 1.0000 Uani . C27 C 0.65765(9) -0.6794(3) -0.04620(6) 0.0354 1.0000 Uani . C28 C 0.64221(9) -0.8200(3) -0.09305(7) 0.0411 1.0000 Uani . C29 C 0.60685(9) -1.0260(3) -0.08833(7) 0.0438 1.0000 Uani . C30 C 0.5868(1) -1.0918(3) -0.03587(8) 0.0471 1.0000 Uani . C31 C 0.6022(1) -0.9525(3) 0.01144(7) 0.0404 1.0000 Uani . N32 N 0.86125(8) -0.1385(2) 0.03116(5) 0.0402 1.0000 Uani . C33 C 0.8680(1) -0.1896(3) -0.02928(7) 0.0454 1.0000 Uani . C34 C 0.8591(1) 0.0258(4) -0.06375(7) 0.0522 1.0000 Uani . C35 C 0.92300(15) 0.1904(4) -0.04869(9) 0.0684 1.0000 Uani . H41 H 0.9663 -0.1611 0.2085 0.0422 1.0000 Uiso . H51 H 1.0751 0.0771 0.2044 0.0519 1.0000 Uiso . H61 H 1.0646 0.4222 0.1519 0.0556 1.0000 Uiso . H71 H 0.9458 0.5281 0.1004 0.0551 1.0000 Uiso . H81 H 0.8374 0.2892 0.1028 0.0452 1.0000 Uiso . H101 H 0.8397 0.2017 0.2438 0.0434 1.0000 Uiso . H111 H 0.7931 0.1896 0.3362 0.0537 1.0000 Uiso . H121 H 0.7260 -0.1323 0.3636 0.0573 1.0000 Uiso . H131 H 0.7030 -0.4458 0.3003 0.0589 1.0000 Uiso . H141 H 0.7479 -0.4376 0.2077 0.0486 1.0000 Uiso . H211 H 0.5296 -0.3884 0.0856 0.0403 1.0000 Uiso . H221 H 0.4652 -0.4263 0.1696 0.0516 1.0000 Uiso . H231 H 0.5069 -0.6998 0.2408 0.0539 1.0000 Uiso . H241 H 0.6126 -0.9354 0.2290 0.0586 1.0000 Uiso . H251 H 0.6786 -0.8955 0.1464 0.0510 1.0000 Uiso . H271 H 0.6836 -0.5287 -0.0507 0.0423 1.0000 Uiso . H281 H 0.6564 -0.7706 -0.1313 0.0490 1.0000 Uiso . H291 H 0.5954 -1.1269 -0.1230 0.0521 1.0000 Uiso . H301 H 0.5594 -1.2413 -0.0322 0.0559 1.0000 Uiso . H311 H 0.5873 -1.0039 0.0499 0.0480 1.0000 Uiso . H331 H 0.9197 -0.2592 -0.0331 0.0575 1.0000 Uiso . H332 H 0.8285 -0.3045 -0.0443 0.0575 1.0000 Uiso . H341 H 0.8558 -0.0102 -0.1055 0.0618 1.0000 Uiso . H342 H 0.8102 0.1006 -0.0560 0.0618 1.0000 Uiso . H351 H 0.9162 0.3340 -0.0715 0.0819 1.0000 Uiso . H352 H 0.9735 0.1208 -0.0563 0.0819 1.0000 Uiso . H353 H 0.9278 0.2317 -0.0068 0.0819 1.0000 Uiso . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0289(7) 0.0267(7) 0.0294(7) -0.0002(5) 0.0054(5) -0.0036(5) C2 0.0297(7) 0.0252(7) 0.0277(6) -0.0004(5) 0.0028(5) 0.0000(6) C3 0.0328(7) 0.0273(7) 0.0263(6) -0.0048(5) 0.0048(5) -0.0036(6) C4 0.0344(8) 0.0411(8) 0.0296(7) 0.0005(6) 0.0012(6) 0.0005(7) C5 0.0302(8) 0.0609(11) 0.0378(8) -0.0064(8) 0.0006(6) -0.0037(8) C6 0.0414(9) 0.052(1) 0.0458(9) -0.0090(8) 0.0079(7) -0.0191(8) C7 0.051(1) 0.0355(9) 0.053(1) 0.0026(8) 0.0047(8) -0.0111(8) C8 0.0378(8) 0.0292(7) 0.0466(9) 0.0016(7) -0.0018(7) -0.0041(7) C9 0.0316(7) 0.0300(7) 0.0259(6) -0.0010(6) 0.0014(5) 0.0041(6) C10 0.0349(8) 0.0394(8) 0.0327(7) -0.0070(6) 0.0026(6) 0.0005(6) C11 0.0435(9) 0.055(1) 0.0340(8) -0.0134(7) 0.0024(7) 0.0054(8) C12 0.051(1) 0.0641(11) 0.0278(7) 0.0007(8) 0.0084(7) 0.0071(9) C13 0.0639(11) 0.051(1) 0.0320(8) 0.0084(7) 0.0098(7) -0.0063(9) C14 0.058(1) 0.0351(8) 0.0297(7) 0.0028(6) 0.0070(7) -0.0038(7) C15 0.0315(7) 0.0303(7) 0.0282(6) -0.0013(6) 0.0049(5) -0.0048(6) O16 0.0365(5) 0.0369(6) 0.0273(5) -0.0061(4) 0.0075(4) -0.0103(4) C17 0.0315(7) 0.0310(7) 0.0247(6) -0.0026(5) 0.0058(5) -0.0016(6) O18 0.0332(5) 0.0364(5) 0.0262(5) -0.0057(4) 0.0071(4) -0.0109(4) C19 0.0287(7) 0.0280(7) 0.0270(6) -0.0013(6) 0.0030(5) -0.0011(6) C20 0.0288(7) 0.0278(7) 0.0286(6) -0.0024(5) 0.0029(5) -0.0050(6) C21 0.0373(8) 0.0331(8) 0.0323(7) 0.0006(6) 0.0047(6) 0.0018(6) C22 0.0420(9) 0.0459(9) 0.0404(8) -0.0026(7) 0.0124(7) 0.0059(7) C23 0.051(1) 0.054(1) 0.0345(8) 0.0022(7) 0.0165(7) -0.0025(8) C24 0.0587(11) 0.053(1) 0.0387(8) 0.0176(8) 0.0121(8) 0.0065(9) C25 0.0415(9) 0.0470(9) 0.0417(9) 0.0108(7) 0.0093(7) 0.0106(8) C26 0.0241(6) 0.0312(7) 0.0308(7) -0.0036(6) 0.0017(5) 0.0003(6) C27 0.0342(8) 0.0392(8) 0.0329(7) -0.0052(6) 0.0037(6) -0.0054(6) C28 0.0391(8) 0.051(1) 0.0333(8) -0.0105(7) 0.0050(6) -0.0022(7) C29 0.0398(9) 0.0444(9) 0.0466(9) -0.0194(8) 0.0021(7) -0.0013(7) C30 0.050(1) 0.0358(9) 0.056(1) -0.0125(8) 0.0067(8) -0.0105(8) C31 0.0458(9) 0.0349(8) 0.0409(8) -0.0054(7) 0.0074(7) -0.0078(7) N32 0.0456(8) 0.0451(8) 0.0315(6) -0.0049(6) 0.0115(6) -0.0142(6) C33 0.054(1) 0.053(1) 0.0325(8) -0.0065(7) 0.0160(7) -0.0206(8) C34 0.0508(11) 0.0697(13) 0.0361(8) 0.0057(9) 0.0053(8) 0.0110(9) C35 0.1086(19) 0.0443(11) 0.0550(12) 0.0109(9) 0.0203(12) -0.0127(11) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.3430(19) yes C1 . C15 . 1.4671(18) yes C1 . O18 . 1.3876(16) yes C2 . C3 . 1.4919(19) yes C2 . C9 . 1.4915(18) yes C3 . C4 . 1.391(2) yes C3 . C8 . 1.387(2) yes C4 . C5 . 1.388(2) yes C4 . H41 . 1.015 no C5 . C6 . 1.383(3) yes C5 . H51 . 1.007 no C6 . C7 . 1.376(3) yes C6 . H61 . 1.011 no C7 . C8 . 1.386(2) yes C7 . H71 . 1.014 no C8 . H81 . 1.006 no C9 . C10 . 1.395(2) yes C9 . C14 . 1.400(2) yes C10 . C11 . 1.394(2) yes C10 . H101 . 1.023 no C11 . C12 . 1.375(3) yes C11 . H111 . 1.014 no C12 . C13 . 1.380(3) yes C12 . H121 . 1.004 no C13 . C14 . 1.387(2) yes C13 . H131 . 1.021 no C14 . H141 . 1.016 no C15 . O16 . 1.4143(17) yes C15 . N32 . 1.2445(18) yes O16 . C17 . 1.3652(16) yes C17 . O18 . 1.3702(16) yes C17 . C19 . 1.3307(19) yes C19 . C20 . 1.5032(18) yes C19 . C26 . 1.4784(19) yes C20 . C21 . 1.387(2) yes C20 . C25 . 1.388(2) yes C21 . C22 . 1.392(2) yes C21 . H211 . 1.015 no C22 . C23 . 1.382(2) yes C22 . H221 . 1.013 no C23 . C24 . 1.373(3) yes C23 . H231 . 1.010 no C24 . C25 . 1.390(2) yes C24 . H241 . 1.008 no C25 . H251 . 1.009 no C26 . C27 . 1.402(2) yes C26 . C31 . 1.394(2) yes C27 . C28 . 1.385(2) yes C27 . H271 . 1.014 no C28 . C29 . 1.380(2) yes C28 . H281 . 1.009 no C29 . C30 . 1.383(3) yes C29 . H291 . 1.014 no C30 . C31 . 1.389(2) yes C30 . H301 . 1.017 no C31 . H311 . 1.020 no N32 . C33 . 1.4757(19) yes C33 . C34 . 1.509(3) yes C33 . H331 . 1.020 no C33 . H332 . 1.010 no C34 . C35 . 1.506(3) yes C34 . H341 . 1.003 no C34 . H342 . 1.009 no C35 . H351 . 1.005 no C35 . H352 . 1.020 no C35 . H353 . 1.013 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . C15 . 132.20(13) yes C2 . C1 . O18 . 121.43(12) yes C15 . C1 . O18 . 106.31(11) yes C1 . C2 . C3 . 119.95(12) yes C1 . C2 . C9 . 122.76(12) yes C3 . C2 . C9 . 117.27(12) yes C2 . C3 . C4 . 119.72(13) yes C2 . C3 . C8 . 121.13(13) yes C4 . C3 . C8 . 119.06(14) yes C3 . C4 . C5 . 120.09(15) yes C3 . C4 . H41 . 119.915 no C5 . C4 . H41 . 119.995 no C4 . C5 . C6 . 120.22(15) yes C4 . C5 . H51 . 120.102 no C6 . C5 . H51 . 119.676 no C5 . C6 . C7 . 119.95(15) yes C5 . C6 . H61 . 119.705 no C7 . C6 . H61 . 120.341 no C6 . C7 . C8 . 120.06(16) yes C6 . C7 . H71 . 119.907 no C8 . C7 . H71 . 120.030 no C3 . C8 . C7 . 120.61(15) yes C3 . C8 . H81 . 119.613 no C7 . C8 . H81 . 119.770 no C2 . C9 . C10 . 119.13(13) yes C2 . C9 . C14 . 122.79(13) yes C10 . C9 . C14 . 118.08(13) yes C9 . C10 . C11 . 120.81(15) yes C9 . C10 . H101 . 119.019 no C11 . C10 . H101 . 120.167 no C10 . C11 . C12 . 120.39(15) yes C10 . C11 . H111 . 120.274 no C12 . C11 . H111 . 119.332 no C11 . C12 . C13 . 119.43(14) yes C11 . C12 . H121 . 120.069 no C13 . C12 . H121 . 120.502 no C12 . C13 . C14 . 120.91(16) yes C12 . C13 . H131 . 119.028 no C14 . C13 . H131 . 120.056 no C9 . C14 . C13 . 120.38(15) yes C9 . C14 . H141 . 119.299 no C13 . C14 . H141 . 120.321 no C1 . C15 . O16 . 105.45(11) yes C1 . C15 . N32 . 131.20(13) yes O16 . C15 . N32 . 123.33(12) yes C15 . O16 . C17 . 108.7(1) yes O16 . C17 . O18 . 109.77(11) yes O16 . C17 . C19 . 127.93(12) yes O18 . C17 . C19 . 122.24(12) yes C1 . O18 . C17 . 109.1(1) yes C17 . C19 . C20 . 115.06(12) yes C17 . C19 . C26 . 124.19(12) yes C20 . C19 . C26 . 120.70(12) yes C19 . C20 . C21 . 120.40(13) yes C19 . C20 . C25 . 120.93(13) yes C21 . C20 . C25 . 118.63(13) yes C20 . C21 . C22 . 120.33(14) yes C20 . C21 . H211 . 119.514 no C22 . C21 . H211 . 120.138 no C21 . C22 . C23 . 120.39(15) yes C21 . C22 . H221 . 120.175 no C23 . C22 . H221 . 119.437 no C22 . C23 . C24 . 119.68(14) yes C22 . C23 . H231 . 120.078 no C24 . C23 . H231 . 120.242 no C23 . C24 . C25 . 120.12(15) yes C23 . C24 . H241 . 119.582 no C25 . C24 . H241 . 120.294 no C20 . C25 . C24 . 120.84(15) yes C20 . C25 . H251 . 119.525 no C24 . C25 . H251 . 119.638 no C19 . C26 . C27 . 122.91(13) yes C19 . C26 . C31 . 119.31(13) yes C27 . C26 . C31 . 117.78(13) yes C26 . C27 . C28 . 120.55(14) yes C26 . C27 . H271 . 119.859 no C28 . C27 . H271 . 119.590 no C27 . C28 . C29 . 121.01(15) yes C27 . C28 . H281 . 119.619 no C29 . C28 . H281 . 119.370 no C28 . C29 . C30 . 119.13(14) yes C28 . C29 . H291 . 120.292 no C30 . C29 . H291 . 120.571 no C29 . C30 . C31 . 120.34(15) yes C29 . C30 . H301 . 119.774 no C31 . C30 . H301 . 119.868 no C26 . C31 . C30 . 121.18(15) yes C26 . C31 . H311 . 119.451 no C30 . C31 . H311 . 119.367 no C15 . N32 . C33 . 120.01(13) yes N32 . C33 . C34 . 109.44(14) yes N32 . C33 . H331 . 109.913 no C34 . C33 . H331 . 109.439 no N32 . C33 . H332 . 110.338 no C34 . C33 . H332 . 110.608 no H331 . C33 . H332 . 107.072 no C33 . C34 . C35 . 112.86(16) yes C33 . C34 . H341 . 109.937 no C35 . C34 . H341 . 108.989 no C33 . C34 . H342 . 108.140 no C35 . C34 . H342 . 108.340 no H341 . C34 . H342 . 108.475 no C34 . C35 . H351 . 112.220 no C34 . C35 . H352 . 110.582 no H351 . C35 . H352 . 107.529 no C34 . C35 . H353 . 111.276 no H351 . C35 . H353 . 108.099 no H352 . C35 . H353 . 106.909 no data_compound_6 _database_code_depnum_ccdc_archive 'CCDC 283684' _audit_creation_date 04-21-05 _audit_creation_method CRYSTALS_ver_12-03-99 _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; H atoms placed geometrically after each cycle ; _publ_section_exptl_prep ; ? ; #========================================================================== _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment noref #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 22.3209(6) _cell_angle_alpha 90 _cell_length_b 5.8220(2) _cell_angle_beta 116.6337(12) _cell_length_c 22.4854(7) _cell_angle_gamma 90 _cell_volume 2611.97(14) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/a ' _symmetry_space_group_name_Hall '-P 2yab' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z x+1/2,-y+1/2,z # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum ' C36 H27 N1 O2 ' _chemical_formula_moiety ' C36 H27 N1 O2 ' _chemical_compound_source ; ? ; _chemical_formula_weight 505.62 _cell_measurement_reflns_used 4324 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 120 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' yellow ' _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.35 _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1064.000 _exptl_absorpt_coefficient_mu 0.079 # Sheldrick geometric definitions 0.98 0.99 _diffrn_measurement_device_type ; Enraf Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 120 _diffrn_reflns_number 10095 _reflns_number_total 5775 _diffrn_reflns_av_R_equivalents 0.02 # Number of reflections with Friedels Law is 5775 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5983 _diffrn_reflns_theta_min 5.104 _diffrn_reflns_theta_max 27.475 _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 23.834 _diffrn_measured_fraction_theta_full 0.973 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _reflns_limit_h_min -28 _reflns_limit_h_max 25 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 29 _refine_diff_density_min -0.21 _refine_diff_density_max 0.20 _refine_ls_number_reflns 3410 _refine_ls_number_parameters 118 #_refine_ls_R_factor_ref 0.0396 _refine_ls_wR_factor_ref 0.0415 _refine_ls_goodness_of_fit_ref 1.0962 #_reflns_number_all 5775 _refine_ls_R_factor_all 0.0840 _refine_ls_wR_factor_all 0.0790 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 3410 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_gt 0.0415 _refine_ls_shift/su_max 0.000369 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight] * [1-(deltaF/6*sigmaF)^2]^2 0.596 0.562E-01 0.207 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 COLLECT Software, Nonius BV 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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_occupancy _atom_site_adp_type _atom_site_attached_hydrogens C1 C 0.66986(8) -0.3294(3) 0.26555(8) 0.0201 1.0000 Uani . C2 C 0.72803(8) -0.4440(3) 0.29579(8) 0.0199 1.0000 Uani . C3 C 0.77793(8) -0.4498(3) 0.26858(8) 0.0203 1.0000 Uani . C4 C 0.81941(9) -0.6421(3) 0.28113(8) 0.0246 1.0000 Uani . C5 C 0.86492(9) -0.6601(3) 0.25501(9) 0.0282 1.0000 Uani . C6 C 0.86953(9) -0.4879(3) 0.21491(9) 0.0291 1.0000 Uani . C7 C 0.82993(9) -0.2944(3) 0.20308(9) 0.0286 1.0000 Uani . C8 C 0.78493(8) -0.2725(3) 0.22974(9) 0.0255 1.0000 Uani . C9 C 0.74401(8) -0.5822(3) 0.35683(8) 0.0199 1.0000 Uani . C10 C 0.80207(8) -0.5387(3) 0.41511(8) 0.0252 1.0000 Uani . C11 C 0.82011(9) -0.6787(3) 0.47041(8) 0.0281 1.0000 Uani . C12 C 0.78069(9) -0.8652(3) 0.46842(9) 0.0273 1.0000 Uani . C13 C 0.72297(9) -0.9098(3) 0.41085(9) 0.0296 1.0000 Uani . C14 C 0.70451(9) -0.7692(3) 0.35550(9) 0.0268 1.0000 Uani . C15 C 0.61596(8) -0.2780(3) 0.28402(8) 0.0203 1.0000 Uani . O16 O 0.57581(6) -0.1108(2) 0.23824(6) 0.0230 1.0000 Uani . C17 C 0.60154(8) -0.0650(3) 0.19459(8) 0.0206 1.0000 Uani . O18 O 0.65319(6) -0.2134(2) 0.20607(5) 0.0232 1.0000 Uani . C19 C 0.58292(8) 0.1002(3) 0.14859(8) 0.0200 1.0000 Uani . C20 C 0.53051(8) 0.2729(3) 0.13838(8) 0.0195 1.0000 Uani . C21 C 0.5049(1) 0.3135(3) 0.18396(9) 0.0318 1.0000 Uani . C22 C 0.4565(1) 0.4792(3) 0.1719(1) 0.0341 1.0000 Uani . C23 C 0.43203(9) 0.6110(3) 0.11486(9) 0.0291 1.0000 Uani . C24 C 0.4583(1) 0.5793(4) 0.07059(9) 0.0373 1.0000 Uani . C25 C 0.5067(1) 0.4120(4) 0.08208(9) 0.0327 1.0000 Uani . C26 C 0.62046(8) 0.1066(3) 0.10746(8) 0.0212 1.0000 Uani . C27 C 0.66420(9) 0.2859(3) 0.11434(9) 0.0294 1.0000 Uani . C28 C 0.70246(9) 0.2848(4) 0.0794(1) 0.0380 1.0000 Uani . C29 C 0.6962(1) 0.1067(4) 0.0368(1) 0.0395 1.0000 Uani . C30 C 0.65204(13) -0.0700(4) 0.02833(11) 0.0424 1.0000 Uani . C31 C 0.61431(11) -0.0706(3) 0.0637(1) 0.0343 1.0000 Uani . N32 N 0.60419(7) -0.3515(3) 0.33007(7) 0.0234 1.0000 Uani . C33 C 0.54645(9) -0.2534(3) 0.33581(9) 0.0282 1.0000 Uani . C34 C 0.51936(8) -0.4131(3) 0.37122(8) 0.0218 1.0000 Uani . C35 C 0.55120(9) -0.6170(3) 0.40074(9) 0.0260 1.0000 Uani . C36 C 0.52394(9) -0.7586(3) 0.43235(9) 0.0281 1.0000 Uani . C37 C 0.46517(9) -0.6980(3) 0.43467(9) 0.0288 1.0000 Uani . C38 C 0.43331(9) -0.4943(3) 0.40559(9) 0.0266 1.0000 Uani . C39 C 0.46000(8) -0.3525(3) 0.37402(8) 0.0246 1.0000 Uani . H41 H 0.8165 -0.7692 0.3102 0.0293 1.0000 Uiso . H51 H 0.8948 -0.7994 0.2652 0.0352 1.0000 Uiso . H61 H 0.9009 -0.5032 0.1941 0.0355 1.0000 Uiso . H71 H 0.8339 -0.1670 0.1746 0.0351 1.0000 Uiso . H81 H 0.7572 -0.1273 0.2217 0.0314 1.0000 Uiso . H101 H 0.8316 -0.4049 0.4169 0.0323 1.0000 Uiso . H111 H 0.8621 -0.6446 0.5124 0.0341 1.0000 Uiso . H121 H 0.7934 -0.9663 0.5088 0.0336 1.0000 Uiso . H131 H 0.6942 -1.0456 0.4090 0.0348 1.0000 Uiso . H141 H 0.6622 -0.8024 0.3138 0.0312 1.0000 Uiso . H211 H 0.5223 0.2203 0.2265 0.0430 1.0000 Uiso . H221 H 0.4385 0.5049 0.2053 0.0439 1.0000 Uiso . H231 H 0.3957 0.7281 0.1059 0.0350 1.0000 Uiso . H241 H 0.4414 0.6763 0.0289 0.0470 1.0000 Uiso . H251 H 0.5252 0.3911 0.0490 0.0408 1.0000 Uiso . H271 H 0.6686 0.4175 0.1457 0.0360 1.0000 Uiso . H281 H 0.7350 0.4142 0.0855 0.0472 1.0000 Uiso . H291 H 0.7238 0.1068 0.0113 0.0498 1.0000 Uiso . H301 H 0.6469 -0.1991 -0.0037 0.0585 1.0000 Uiso . H311 H 0.5818 -0.2010 0.0577 0.0459 1.0000 Uiso . H331 H 0.5602 -0.1043 0.3612 0.0395 1.0000 Uiso . H332 H 0.5098 -0.2200 0.2900 0.0395 1.0000 Uiso . H351 H 0.5938 -0.6620 0.3986 0.0313 1.0000 Uiso . H361 H 0.5477 -0.9065 0.4538 0.0362 1.0000 Uiso . H371 H 0.4458 -0.8016 0.4577 0.0355 1.0000 Uiso . H381 H 0.3908 -0.4492 0.4081 0.0330 1.0000 Uiso . H391 H 0.4363 -0.2050 0.3524 0.0308 1.0000 Uiso . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0222 0.0191 0.0192 0.0027 0.0093 -0.0012 C2 0.0197 0.0165 0.0220 -0.0001 0.0081 -0.0022 C3 0.0172 0.0205 0.0201 -0.0012 0.0055 -0.0014 C4 0.0266 0.0239 0.0238 0.0010 0.0117 0.0013 C5 0.0296 0.0279 0.0285 0.0012 0.0144 0.0068 C6 0.0229 0.0398 0.0278 -0.0015 0.0142 -0.0009 C7 0.0238 0.0330 0.0292 0.0046 0.0121 -0.0055 C8 0.0219 0.0229 0.0304 0.0041 0.0104 -0.0014 C9 0.0188 0.0190 0.0235 0.0001 0.0107 0.0027 C10 0.0214 0.0300 0.0249 -0.0005 0.0109 -0.0057 C11 0.0220 0.0386 0.0220 0.0001 0.0082 -0.0032 C12 0.0287 0.0277 0.0263 0.0057 0.0130 0.0034 C13 0.0327 0.0217 0.0324 0.0050 0.0129 -0.0038 C14 0.0256 0.0232 0.0260 0.0012 0.0067 -0.0030 C15 0.0194 0.0186 0.0205 0.0032 0.0068 0.0004 O16 0.0224 0.0240 0.0250 0.0072 0.0127 0.0037 C17 0.0172 0.0233 0.0219 -0.0006 0.0092 0.0000 O18 0.0224 0.0260 0.0236 0.0067 0.0124 0.0073 C19 0.0195 0.0210 0.0192 -0.0010 0.0084 -0.0010 C20 0.0168 0.0197 0.0209 0.0001 0.0076 -0.0008 C21 0.0396 0.0317 0.0320 0.0102 0.0230 0.0097 C22 0.0397 0.0349 0.0396 0.0081 0.0285 0.0112 C23 0.0285 0.0303 0.0293 0.0045 0.0136 0.0106 C24 0.0427 0.0445 0.0282 0.0139 0.0190 0.0225 C25 0.0350 0.0422 0.0262 0.0083 0.0183 0.0159 C26 0.0199 0.0230 0.0198 0.0059 0.0080 0.0054 C27 0.0266 0.0348 0.0263 -0.0034 0.0116 -0.0065 C28 0.0274 0.0545 0.0338 0.0009 0.0154 -0.0098 C29 0.0377 0.0531 0.0379 0.0114 0.0261 0.0149 C30 0.0705 0.0294 0.0455 0.0016 0.0423 0.0093 C31 0.0521 0.0216 0.0400 0.0002 0.0304 -0.0006 N32 0.0219 0.0257 0.0250 0.0037 0.0125 0.0023 C33 0.0284 0.0297 0.0331 0.0081 0.0196 0.0052 C34 0.0205 0.0252 0.0191 -0.0004 0.0083 -0.0019 C35 0.0232 0.0277 0.0281 0.0021 0.0125 0.0006 C36 0.0293 0.0240 0.0324 0.0051 0.0151 0.0002 C37 0.0294 0.0311 0.0284 -0.0008 0.0150 -0.0068 C38 0.0233 0.0322 0.0271 -0.0049 0.0138 -0.0027 C39 0.0229 0.0274 0.0230 -0.0009 0.0098 0.0011 _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.342(2) yes C1 . C15 . 1.469(2) yes C1 . O18 . 1.3921(19) yes C2 . C3 . 1.492(2) yes C2 . C9 . 1.490(2) yes C3 . C4 . 1.399(2) yes C3 . C8 . 1.406(2) yes C4 . C5 . 1.386(2) yes C4 . H41 . 1.009 no C5 . C6 . 1.383(3) yes C5 . H51 . 1.009 no C6 . C7 . 1.382(3) yes C6 . H61 . 1.005 no C7 . C8 . 1.387(2) yes C7 . H71 . 1.009 no C8 . H81 . 1.015 no C9 . C10 . 1.392(2) yes C9 . C14 . 1.393(2) yes C10 . C11 . 1.387(2) yes C10 . H101 . 1.010 no C11 . C12 . 1.386(3) yes C11 . H111 . 1.008 no C12 . C13 . 1.381(3) yes C12 . H121 . 1.011 no C13 . C14 . 1.389(2) yes C13 . H131 . 1.007 no C14 . H141 . 1.007 no C15 . O16 . 1.4082(19) yes C15 . N32 . 1.252(2) yes O16 . C17 . 1.3675(19) yes C17 . O18 . 1.369(2) yes C17 . C19 . 1.335(2) yes C19 . C20 . 1.480(2) yes C19 . C26 . 1.501(2) yes C20 . C21 . 1.399(2) yes C20 . C25 . 1.392(2) yes C21 . C22 . 1.382(3) yes C21 . H211 . 1.013 no C22 . C23 . 1.380(3) yes C22 . H221 . 1.010 no C23 . C24 . 1.375(3) yes C23 . H231 . 1.009 no C24 . C25 . 1.390(3) yes C24 . H241 . 1.012 no C25 . H251 . 1.009 no C26 . C27 . 1.390(2) yes C26 . C31 . 1.390(2) yes C27 . C28 . 1.395(3) yes C27 . H271 . 1.015 no C28 . C29 . 1.376(3) yes C28 . H281 . 1.013 no C29 . C30 . 1.378(3) yes C29 . H291 . 1.012 no C30 . C31 . 1.393(3) yes C30 . H301 . 1.012 no C31 . H311 . 1.016 no N32 . C33 . 1.467(2) yes C33 . C34 . 1.515(2) yes C33 . H331 . 1.008 no C33 . H332 . 1.006 no C34 . C35 . 1.390(2) yes C34 . C39 . 1.399(2) yes C35 . C36 . 1.394(2) yes C35 . H351 . 1.007 no C36 . C37 . 1.382(3) yes C36 . H361 . 1.013 no C37 . C38 . 1.387(3) yes C37 . H371 . 1.010 no C38 . C39 . 1.385(2) yes C38 . H381 . 1.011 no C39 . H391 . 1.012 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . C15 . 133.40(15) yes C2 . C1 . O18 . 120.61(14) yes C15 . C1 . O18 . 105.82(13) yes C1 . C2 . C3 . 122.28(15) yes C1 . C2 . C9 . 120.86(14) yes C3 . C2 . C9 . 116.79(14) yes C2 . C3 . C4 . 118.94(15) yes C2 . C3 . C8 . 123.31(15) yes C4 . C3 . C8 . 117.73(15) yes C3 . C4 . C5 . 121.29(16) yes C3 . C4 . H41 . 119.243 no C5 . C4 . H41 . 119.465 no C4 . C5 . C6 . 120.30(17) yes C4 . C5 . H51 . 119.950 no C6 . C5 . H51 . 119.754 no C5 . C6 . C7 . 119.22(16) yes C5 . C6 . H61 . 120.656 no C7 . C6 . H61 . 120.118 no C6 . C7 . C8 . 121.08(17) yes C6 . C7 . H71 . 119.353 no C8 . C7 . H71 . 119.567 no C3 . C8 . C7 . 120.32(16) yes C3 . C8 . H81 . 119.596 no C7 . C8 . H81 . 120.084 no C2 . C9 . C10 . 120.41(15) yes C2 . C9 . C14 . 120.98(15) yes C10 . C9 . C14 . 118.40(15) yes C9 . C10 . C11 . 120.70(16) yes C9 . C10 . H101 . 119.578 no C11 . C10 . H101 . 119.720 no C10 . C11 . C12 . 120.44(16) yes C10 . C11 . H111 . 119.847 no C12 . C11 . H111 . 119.714 no C11 . C12 . C13 . 119.33(16) yes C11 . C12 . H121 . 120.595 no C13 . C12 . H121 . 120.063 no C12 . C13 . C14 . 120.40(17) yes C12 . C13 . H131 . 119.773 no C14 . C13 . H131 . 119.824 no C9 . C14 . C13 . 120.73(16) yes C9 . C14 . H141 . 119.327 no C13 . C14 . H141 . 119.947 no C1 . C15 . O16 . 105.54(13) yes C1 . C15 . N32 . 131.77(15) yes O16 . C15 . N32 . 122.67(15) yes C15 . O16 . C17 . 108.97(12) yes O16 . C17 . O18 . 109.30(13) yes O16 . C17 . C19 . 127.71(15) yes O18 . C17 . C19 . 122.96(14) yes C1 . O18 . C17 . 109.10(12) yes C17 . C19 . C20 . 124.02(14) yes C17 . C19 . C26 . 115.42(14) yes C20 . C19 . C26 . 120.54(14) yes C19 . C20 . C21 . 123.70(15) yes C19 . C20 . C25 . 119.32(14) yes C21 . C20 . C25 . 116.91(16) yes C20 . C21 . C22 . 120.98(17) yes C20 . C21 . H211 . 119.368 no C22 . C21 . H211 . 119.655 no C21 . C22 . C23 . 121.25(17) yes C21 . C22 . H221 . 119.638 no C23 . C22 . H221 . 119.109 no C22 . C23 . C24 . 118.63(17) yes C22 . C23 . H231 . 120.530 no C24 . C23 . H231 . 120.840 no C23 . C24 . C25 . 120.47(17) yes C23 . C24 . H241 . 119.550 no C25 . C24 . H241 . 119.962 no C20 . C25 . C24 . 121.69(16) yes C20 . C25 . H251 . 119.014 no C24 . C25 . H251 . 119.298 no C19 . C26 . C27 . 120.54(15) yes C19 . C26 . C31 . 120.87(15) yes C27 . C26 . C31 . 118.54(16) yes C26 . C27 . C28 . 120.70(18) yes C26 . C27 . H271 . 119.280 no C28 . C27 . H271 . 120.019 no C27 . C28 . C29 . 119.95(19) yes C27 . C28 . H281 . 120.287 no C29 . C28 . H281 . 119.767 no C28 . C29 . C30 . 120.07(17) yes C28 . C29 . H291 . 119.758 no C30 . C29 . H291 . 120.166 no C29 . C30 . C31 . 120.11(19) yes C29 . C30 . H301 . 119.877 no C31 . C30 . H301 . 120.010 no C26 . C31 . C30 . 120.60(18) yes C26 . C31 . H311 . 119.069 no C30 . C31 . H311 . 120.327 no C15 . N32 . C33 . 117.26(14) yes N32 . C33 . C34 . 112.39(15) yes N32 . C33 . H331 . 109.098 no C34 . C33 . H331 . 108.891 no N32 . C33 . H332 . 109.214 no C34 . C33 . H332 . 108.844 no H331 . C33 . H332 . 108.317 no C33 . C34 . C35 . 122.40(15) yes C33 . C34 . C39 . 118.56(15) yes C35 . C34 . C39 . 119.04(16) yes C34 . C35 . C36 . 120.12(16) yes C34 . C35 . H351 . 119.353 no C36 . C35 . H351 . 120.519 no C35 . C36 . C37 . 120.48(17) yes C35 . C36 . H361 . 119.336 no C37 . C36 . H361 . 120.179 no C36 . C37 . C38 . 119.68(16) yes C36 . C37 . H371 . 119.982 no C38 . C37 . H371 . 120.333 no C37 . C38 . C39 . 120.25(16) yes C37 . C38 . H381 . 119.441 no C39 . C38 . H381 . 120.306 no C34 . C39 . C38 . 120.42(16) yes C34 . C39 . H391 . 119.626 no C38 . C39 . H391 . 119.955 no