Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. # 1. SUBMISSION DETAILS _journal_coden_Cambridge 0177 _publ_requested_category ' ?' _publ_contact_author_name 'Martin G. Banwell' _publ_contact_author_address ; Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' 61 2 6125 8202 ' _publ_contact_author_fax ' 61 2 6125 8114 ' _publ_contact_author_email mgb@rsc.anu.edu.au _publ_section_title ; A chemoenzymatic total synthesis of the phytoactive undecenolide (+)-cladospolide B via a mid-stage ring-closing metathesis and a late-stage photo-isomerisation of the E-isomer ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address K.A.Austin ; Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia ; M.G.Banwell ; Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia ; D.T.J.Loong ; Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia ; A.D.Rae ; Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia ; A.C.Willis ; Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia ; #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; The crystal structure of C~18~H~30~O~6~ is reported. ; _publ_section_comment #Text of the paper ; The crystallographic asymmetric unit consists of one C~18~H~30~O~6~ molecule. Hydrogen atoms were included at calculated positions and during refinement they ride on the atom to which they are attached. The compound is enantiometrically pure but the anomolous dispersion terms are very low for all elements in the structure and so the absolute configuration can not be determined in this experiment. Consequently Friedel-pair reflections have been averaged and the Flack parameter has not been refined. The absolute configuration of the molecule has been assigned on the basis of the synthetic precursors. ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; Hydrogen atoms were included at calculated positions and during refinement they ride on the atom to which they are attached. ; _publ_section_exptl_prep ; The compound was prepared by DTL and recrystallized from hexane. The sample ID is DTL#25. ; #========================================================================== data_mgb044 _database_code_depnum_ccdc_archive 'CCDC 253913' _audit_creation_date 04-27-04 _audit_creation_method CRYSTALS_ver_12-03-99 # 4270930 mgb044 _audit_update_record ; 2004-04-27 - Report on C18 H30 O6 by Anthony C. Willis for David Loong and Martin Banwell 2004-04-15 - passes checkcif tests with minor warnings ; _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 2003) ; _computing_publication_material ; CRYSTALS (Watkin et al 2003) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 7.04350(10) _cell_angle_alpha 90 _cell_length_b 16.1734(4) _cell_angle_beta 90 _cell_length_c 16.3288(4) _cell_angle_gamma 90 _cell_volume 1860.13(7) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,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 syn _refine_ls_abs_structure_details ; The enantiomer has been assigned by reference to an unchanging chiral centre in the synthetic procedure. ; 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 _cell_formula_units_Z 4 _chemical_formula_sum ' C18 H30 O6 ' _chemical_formula_moiety ' C18 H30 O6 ' _chemical_compound_source ; ? ; _chemical_formula_weight 342.43 _cell_measurement_reflns_used 10470 _cell_measurement_theta_min 3 _cell_measurement_theta_max 25 _cell_measurement_temperature 200 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.223 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.090 _diffrn_measurement_device_type ; 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 ' \f and \w scans with CCD ' _diffrn_special_details ; CCD data collecting conditions- phi and omega scans of width 2.0 deg at rate 480 sec/frame, crystal-detector distance 28mm, multiple scan sets so over 95 percent of data collected with 4-fold redundancy or more. ; # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.923 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) in maXus ; # Sheldrick geometric definitions 0.99 1.00 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 200 _diffrn_reflns_number 18812 _reflns_number_total 1903 _diffrn_reflns_av_R_equivalents 0.05 # Number of reflections with Friedels Law is 1903 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1642 _diffrn_reflns_theta_min 2.795 _diffrn_reflns_theta_max 25.022 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.022 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min 0 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 19 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _refine_diff_density_min -0.15 _refine_diff_density_max 0.12 _refine_ls_number_reflns 1399 _refine_ls_number_restraints 0 _refine_ls_number_parameters 217 #_refine_ls_R_factor_ref 0.0276 _refine_ls_wR_factor_ref 0.0297 _refine_ls_goodness_of_fit_ref 1.1307 #_reflns_number_all 1892 _refine_ls_R_factor_all 0.0431 _refine_ls_wR_factor_all 0.0340 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 1399 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_gt 0.0297 _refine_ls_shift/su_max 0.00021 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.798 0.489 0.795 0.164 0.223 ; _refine_ls_extinction_method None _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (2000). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Blessing, R. H.; Acta Crystallogr., Section A, 51, 33-37 (1995). Blessing, R. H.; J. Appl. Crystallogr., 30, 421-426 (1997). 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 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, 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. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994), Acta Cryst, A50, 411-437 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_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C1 C 0.4735(3) 0.07060(15) 0.48242(14) 0.0308 1.0000 Uani . . . . . . C2 C 0.4753(3) 0.09939(15) 0.39623(14) 0.0296 1.0000 Uani . . . . . . C3 C 0.4804(3) 0.17955(15) 0.38028(14) 0.0283 1.0000 Uani . . . . . . C4 C 0.4250(3) 0.21539(14) 0.29962(14) 0.0276 1.0000 Uani . . . . . . C5 C 0.2317(3) 0.25908(15) 0.30463(14) 0.0283 1.0000 Uani . . . . . . C6 C 0.0653(4) 0.20173(16) 0.32492(14) 0.0340 1.0000 Uani . . . . . . C7 C 0.0369(4) 0.18849(15) 0.41779(14) 0.0335 1.0000 Uani . . . . . . C8 C 0.0111(3) 0.09827(15) 0.44326(14) 0.0322 1.0000 Uani . . . . . . C9 C 0.0304(4) 0.08556(16) 0.53637(14) 0.0367 1.0000 Uani . . . . . . C10 C 0.0767(4) -0.00362(17) 0.56138(16) 0.0374 1.0000 Uani . . . . . . C11 C 0.2883(4) -0.02286(16) 0.56605(15) 0.0365 1.0000 Uani . . . . . . O12 O 0.3734(2) -0.00035(10) 0.48727(9) 0.0321 1.0000 Uani . . . . . . O13 O 0.5399(3) 0.10676(12) 0.54013(11) 0.0441 1.0000 Uani . . . . . . C14 C 0.3294(5) -0.11355(18) 0.5791(2) 0.0600 1.0000 Uani . . . . . . O15 O 0.5669(2) 0.27463(9) 0.27722(9) 0.0288 1.0000 Uani . . . . . . C16 C 0.5343(4) 0.31396(14) 0.20023(14) 0.0288 1.0000 Uani . . . . . . C17 C 0.3321(3) 0.35194(15) 0.19780(14) 0.0294 1.0000 Uani . . . . . . O18 O 0.1942(2) 0.29380(9) 0.22486(9) 0.0295 1.0000 Uani . . . . . . O19 O 0.5329(2) 0.25395(10) 0.13650(9) 0.0347 1.0000 Uani . . . . . . C20 C 0.7029(4) 0.20793(17) 0.12641(18) 0.0480 1.0000 Uani . . . . . . C21 C 0.6920(4) 0.37655(16) 0.19157(16) 0.0364 1.0000 Uani . . . . . . O22 O 0.3436(2) 0.42034(9) 0.25198(10) 0.0340 1.0000 Uani . . . . . . C23 C 0.1723(4) 0.46457(17) 0.26583(18) 0.0434 1.0000 Uani . . . . . . C24 C 0.2691(4) 0.37589(16) 0.11207(15) 0.0378 1.0000 Uani . . . . . . H21 H 0.4727(3) 0.05842(15) 0.35037(14) 0.0355 1.0000 Uiso R . . . . . H31 H 0.5235(3) 0.21800(15) 0.42449(14) 0.0340 1.0000 Uiso R . . . . . H41 H 0.4146(3) 0.17002(14) 0.25826(14) 0.0330 1.0000 Uiso R . . . . . H51 H 0.2405(3) 0.30074(15) 0.34972(14) 0.0339 1.0000 Uiso R . . . . . H61 H -0.0535(4) 0.22633(16) 0.30181(14) 0.0408 1.0000 Uiso R . . . . . H62 H 0.0892(4) 0.14679(16) 0.29879(14) 0.0408 1.0000 Uiso R . . . . . H71 H 0.1508(4) 0.21089(15) 0.44688(14) 0.0402 1.0000 Uiso R . . . . . H72 H -0.0785(4) 0.21996(15) 0.43511(14) 0.0402 1.0000 Uiso R . . . . . H81 H -0.1181(3) 0.07958(15) 0.42589(14) 0.0386 1.0000 Uiso R . . . . . H82 H 0.1096(3) 0.06407(15) 0.41502(14) 0.0386 1.0000 Uiso R . . . . . H91 H -0.0923(4) 0.10168(16) 0.56276(14) 0.0440 1.0000 Uiso R . . . . . H92 H 0.1342(4) 0.12232(16) 0.55679(14) 0.0440 1.0000 Uiso R . . . . . H101 H 0.0198(4) -0.01402(17) 0.61653(16) 0.0448 1.0000 Uiso R . . . . . H102 H 0.0179(4) -0.04172(17) 0.52037(16) 0.0448 1.0000 Uiso R . . . . . H111 H 0.3411(4) 0.00874(16) 0.61352(15) 0.0438 1.0000 Uiso R . . . . . H141 H 0.4698(5) -0.12233(18) 0.5817(2) 0.0719 1.0000 Uiso R . . . . . H142 H 0.2704(5) -0.13210(18) 0.6317(2) 0.0719 1.0000 Uiso R . . . . . H143 H 0.2752(5) -0.14627(18) 0.5327(2) 0.0719 1.0000 Uiso R . . . . . H201 H 0.6869(4) 0.16777(17) 0.08036(18) 0.0576 1.0000 Uiso R . . . . . H202 H 0.8099(4) 0.24646(17) 0.11371(18) 0.0576 1.0000 Uiso R . . . . . H203 H 0.7315(4) 0.17713(17) 0.17806(18) 0.0576 1.0000 Uiso R . . . . . H211 H 0.6777(4) 0.40665(16) 0.13843(16) 0.0436 1.0000 Uiso R . . . . . H212 H 0.6855(4) 0.41693(16) 0.23786(16) 0.0436 1.0000 Uiso R . . . . . H213 H 0.8173(4) 0.34754(16) 0.19268(16) 0.0436 1.0000 Uiso R . . . . . H231 H 0.1969(4) 0.51114(17) 0.30470(18) 0.0520 1.0000 Uiso R . . . . . H232 H 0.1243(4) 0.48719(17) 0.21272(18) 0.0520 1.0000 Uiso R . . . . . H233 H 0.0752(4) 0.42652(17) 0.28981(18) 0.0520 1.0000 Uiso R . . . . . H241 H 0.1383(4) 0.39989(16) 0.11439(15) 0.0453 1.0000 Uiso R . . . . . H242 H 0.3589(4) 0.41780(16) 0.08914(15) 0.0453 1.0000 Uiso R . . . . . H243 H 0.2685(4) 0.32573(16) 0.07626(15) 0.0453 1.0000 Uiso R . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0253(11) 0.0333(12) 0.0337(12) 0.0045(11) -0.0011(11) 0.0038(11) C2 0.0258(12) 0.0332(13) 0.0298(12) 0.0023(10) 0.0021(10) 0.0035(10) C3 0.0243(12) 0.0331(13) 0.0276(11) 0.0012(10) -0.0030(10) -0.0021(10) C4 0.0281(12) 0.0268(11) 0.0277(12) 0.0041(10) -0.0009(10) -0.0035(10) C5 0.0294(12) 0.0318(12) 0.0236(12) 0.0036(10) -0.0034(10) -0.0001(11) C6 0.0297(13) 0.0390(14) 0.0334(13) 0.0029(11) -0.0012(11) -0.0083(12) C7 0.0294(13) 0.0360(13) 0.0352(13) 0.0020(11) 0.0025(11) -0.0020(12) C8 0.0271(12) 0.0373(13) 0.0322(12) 0.0039(11) 0.0023(11) 0.0020(11) C9 0.0363(13) 0.0419(15) 0.0320(13) 0.0015(11) 0.0057(11) 0.0062(13) C10 0.0378(13) 0.0413(14) 0.0330(13) 0.0072(12) 0.0024(11) -0.0022(13) C11 0.0384(15) 0.0443(15) 0.0268(13) 0.0074(12) 0.0055(12) 0.0011(12) O12 0.0362(9) 0.0304(8) 0.0299(9) 0.0046(7) 0.0055(7) 0.0005(8) O13 0.0472(10) 0.0483(10) 0.0368(10) 0.0064(9) -0.0108(9) -0.0109(9) C14 0.0573(19) 0.0531(18) 0.070(2) 0.0283(16) 0.0157(18) 0.0102(17) O15 0.0259(8) 0.0318(9) 0.0286(8) 0.0050(7) -0.0021(7) -0.0028(7) C16 0.0316(12) 0.0293(12) 0.0254(11) 0.0019(10) -0.0011(11) -0.0012(11) C17 0.0271(12) 0.0312(12) 0.0300(12) 0.0017(10) -0.0023(11) -0.0030(10) O18 0.0261(8) 0.0341(9) 0.0282(8) 0.0060(7) -0.0036(7) -0.0037(7) O19 0.0356(9) 0.0382(9) 0.0303(8) -0.0045(7) 0.0013(8) 0.0057(9) C20 0.0437(16) 0.0462(15) 0.0542(17) -0.0115(14) 0.0058(15) 0.0098(14) C21 0.0297(13) 0.0397(14) 0.0397(14) 0.0059(12) 0.0008(12) -0.0045(12) O22 0.0299(9) 0.0299(9) 0.0423(9) -0.0031(8) -0.0008(8) 0.0013(8) C23 0.0374(14) 0.0441(14) 0.0487(16) -0.0007(13) 0.0025(13) 0.0093(13) C24 0.0366(14) 0.0420(14) 0.0348(14) 0.0123(12) -0.0050(11) -0.0025(12) 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 . 1.482(3) yes C1 . O12 . 1.349(3) yes C1 . O13 . 1.204(3) yes C2 . C3 . 1.323(3) yes C2 . H21 . 1.000 no C3 . C4 . 1.491(3) yes C3 . H31 . 1.000 no C4 . C5 . 1.536(3) yes C4 . O15 . 1.432(3) yes C4 . H41 . 1.000 no C5 . C6 . 1.531(3) yes C5 . O18 . 1.443(3) yes C5 . H51 . 1.000 no C6 . C7 . 1.545(3) yes C6 . H61 . 1.000 no C6 . H62 . 1.000 no C7 . C8 . 1.528(3) yes C7 . H71 . 1.000 no C7 . H72 . 1.000 no C8 . C9 . 1.540(3) yes C8 . H81 . 1.000 no C8 . H82 . 1.000 no C9 . C10 . 1.534(4) yes C9 . H91 . 1.000 no C9 . H92 . 1.000 no C10 . C11 . 1.524(3) yes C10 . H101 . 1.000 no C10 . H102 . 1.000 no C11 . O12 . 1.465(3) yes C11 . C14 . 1.510(4) yes C11 . H111 . 1.000 no C14 . H141 . 1.000 no C14 . H142 . 1.000 no C14 . H143 . 1.000 no O15 . C16 . 1.428(3) yes C16 . C17 . 1.551(3) yes C16 . O19 . 1.423(3) yes C16 . C21 . 1.510(3) yes C17 . O18 . 1.422(3) yes C17 . O22 . 1.419(3) yes C17 . C24 . 1.519(3) yes O19 . C20 . 1.419(3) yes C20 . H201 . 1.000 no C20 . H202 . 1.000 no C20 . H203 . 1.000 no C21 . H211 . 1.000 no C21 . H212 . 1.000 no C21 . H213 . 1.000 no O22 . C23 . 1.421(3) yes C23 . H231 . 1.000 no C23 . H232 . 1.000 no C23 . H233 . 1.000 no C24 . H241 . 1.000 no C24 . H242 . 1.000 no C24 . H243 . 1.000 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 . O12 . 109.1(2) yes C2 . C1 . O13 . 126.0(2) yes O12 . C1 . O13 . 124.8(2) yes C1 . C2 . C3 . 119.7(2) yes C1 . C2 . H21 . 120.168 no C3 . C2 . H21 . 120.164 no C2 . C3 . C4 . 123.2(2) yes C2 . C3 . H31 . 118.389 no C4 . C3 . H31 . 118.383 no C3 . C4 . C5 . 111.34(19) yes C3 . C4 . O15 . 107.64(18) yes C5 . C4 . O15 . 108.94(17) yes C3 . C4 . H41 . 109.288 no C5 . C4 . H41 . 107.997 no O15 . C4 . H41 . 111.671 no C4 . C5 . C6 . 114.29(18) yes C4 . C5 . O18 . 107.05(18) yes C6 . C5 . O18 . 106.91(18) yes C4 . C5 . H51 . 107.109 no C6 . C5 . H51 . 107.243 no O18 . C5 . H51 . 114.445 no C5 . C6 . C7 . 113.3(2) yes C5 . C6 . H61 . 108.513 no C7 . C6 . H61 . 108.505 no C5 . C6 . H62 . 108.499 no C7 . C6 . H62 . 108.509 no H61 . C6 . H62 . 109.467 no C6 . C7 . C8 . 114.5(2) yes C6 . C7 . H71 . 108.195 no C8 . C7 . H71 . 108.189 no C6 . C7 . H72 . 108.190 no C8 . C7 . H72 . 108.207 no H71 . C7 . H72 . 109.467 no C7 . C8 . C9 . 112.7(2) yes C7 . C8 . H81 . 108.653 no C9 . C8 . H81 . 108.655 no C7 . C8 . H82 . 108.677 no C9 . C8 . H82 . 108.669 no H81 . C8 . H82 . 109.467 no C8 . C9 . C10 . 114.0(2) yes C8 . C9 . H91 . 108.328 no C10 . C9 . H91 . 108.317 no C8 . C9 . H92 . 108.319 no C10 . C9 . H92 . 108.328 no H91 . C9 . H92 . 109.467 no C9 . C10 . C11 . 114.4(2) yes C9 . C10 . H101 . 108.214 no C11 . C10 . H101 . 108.210 no C9 . C10 . H102 . 108.229 no C11 . C10 . H102 . 108.237 no H101 . C10 . H102 . 109.467 no C10 . C11 . O12 . 107.77(19) yes C10 . C11 . C14 . 113.1(2) yes O12 . C11 . C14 . 106.7(2) yes C10 . C11 . H111 . 107.322 no O12 . C11 . H111 . 113.678 no C14 . C11 . H111 . 108.390 no C11 . O12 . C1 . 118.47(18) yes C11 . C14 . H141 . 109.455 no C11 . C14 . H142 . 109.463 no H141 . C14 . H142 . 109.476 no C11 . C14 . H143 . 109.482 no H141 . C14 . H143 . 109.476 no H142 . C14 . H143 . 109.476 no C4 . O15 . C16 . 114.25(17) yes O15 . C16 . C17 . 110.28(19) yes O15 . C16 . O19 . 109.95(17) yes C17 . C16 . O19 . 104.19(18) yes O15 . C16 . C21 . 105.24(19) yes C17 . C16 . C21 . 114.05(19) yes O19 . C16 . C21 . 113.2(2) yes C16 . C17 . O18 . 110.93(18) yes C16 . C17 . O22 . 103.90(18) yes O18 . C17 . O22 . 111.15(18) yes C16 . C17 . C24 . 113.1(2) yes O18 . C17 . C24 . 104.80(19) yes O22 . C17 . C24 . 113.12(19) yes C5 . O18 . C17 . 114.37(16) yes C16 . O19 . C20 . 115.91(19) yes O19 . C20 . H201 . 109.459 no O19 . C20 . H202 . 109.469 no H201 . C20 . H202 . 109.476 no O19 . C20 . H203 . 109.472 no H201 . C20 . H203 . 109.476 no H202 . C20 . H203 . 109.476 no C16 . C21 . H211 . 109.469 no C16 . C21 . H212 . 109.465 no H211 . C21 . H212 . 109.476 no C16 . C21 . H213 . 109.466 no H211 . C21 . H213 . 109.476 no H212 . C21 . H213 . 109.476 no C17 . O22 . C23 . 116.30(18) yes O22 . C23 . H231 . 109.465 no O22 . C23 . H232 . 109.463 no H231 . C23 . H232 . 109.476 no O22 . C23 . H233 . 109.472 no H231 . C23 . H233 . 109.476 no H232 . C23 . H233 . 109.476 no C17 . C24 . H241 . 109.467 no C17 . C24 . H242 . 109.467 no H241 . C24 . H242 . 109.476 no C17 . C24 . H243 . 109.466 no H241 . C24 . H243 . 109.476 no H242 . C24 . H243 . 109.476 no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O12 C21 3.564(3) . 3_645 no O13 C7 3.382(3) . 2_556 no O13 C9 3.472(4) . 1_655 no O13 C23 3.499(3) . 2_556 no O13 C5 3.600(3) . 2_556 no O19 C14 3.542(4) . 4_554 no #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O12 C1 C2 C3 . . . . 148.1(2) no O12 C11 C10 C9 . . . . -54.3(3) no O13 C1 O12 C11 . . . . 19.7(3) no O13 C1 C2 C3 . . . . -27.6(3) no O15 C4 C3 C2 . . . . -134.5(2) no O15 C4 C5 O18 . . . . 59.5(2) no O15 C4 C5 C6 . . . . 177.7(2) no O15 C16 O19 C20 . . . . -60.5(3) no O15 C16 C17 O18 . . . . -48.4(2) no O15 C16 C17 O22 . . . . 71.2(2) no O15 C16 C17 C24 . . . . -165.8(2) no O18 C5 C4 C3 . . . . 178.1(2) no O18 C5 C6 C7 . . . . -155.8(2) no O18 C17 O22 C23 . . . . -56.9(2) no O18 C17 C16 O19 . . . . 69.6(2) no O18 C17 C16 C21 . . . . -166.5(2) no O19 C16 O15 C4 . . . . -61.1(2) no O19 C16 C17 O22 . . . . -170.9(2) no O19 C16 C17 C24 . . . . -47.9(2) no O22 C17 O18 C5 . . . . -60.5(2) no O22 C17 C16 C21 . . . . -47.0(2) no C1 O12 C11 C10 . . . . 103.0(2) no C1 O12 C11 C14 . . . . -135.2(2) no C1 C2 C3 C4 . . . . -161.0(2) no C2 C1 O12 C11 . . . . -156.0(2) no C2 C3 C4 C5 . . . . 106.2(2) no C3 C4 O15 C16 . . . . 179.4(2) no C3 C4 C5 C6 . . . . -63.7(2) no C4 O15 C16 C17 . . . . 53.3(2) no C4 O15 C16 C21 . . . . 176.7(2) no C4 C5 O18 C17 . . . . -59.7(2) no C4 C5 C6 C7 . . . . 85.9(3) no C5 O18 C17 C16 . . . . 54.6(2) no C5 O18 C17 C24 . . . . 177.0(2) no C5 C4 O15 C16 . . . . -59.8(2) no C5 C6 C7 C8 . . . . -132.5(2) no C6 C5 O18 C17 . . . . 177.4(2) no C6 C7 C8 C9 . . . . 166.5(2) no C7 C8 C9 C10 . . . . -159.2(2) no C8 C9 C10 C11 . . . . 89.6(3) no C9 C10 C11 C14 . . . . -171.9(2) no C16 C17 O22 C23 . . . . -176.3(2) no C17 C16 O19 C20 . . . . -178.7(2) no C20 O19 C16 C21 . . . . 56.9(3) no C21 C16 C17 C24 . . . . 76.0(3) no C23 O22 C17 C24 . . . . 60.7(3) no #------------------------------------------------------------------------------ #===END # CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98) data_mgb045_rae _database_code_depnum_ccdc_archive 'CCDC 253914' _audit_creation_method maXus _audit_update_record ; 2004-05-14 - Report on C16 H26 O6 by A. David Rae and Anthony C. Willis for David Loong and Martin Banwell 2004-05-14 - passes checkcif tests with minor warnings ; _publ_section_abstract ; The crystal structure of C~16~H~26~O~6~ is reported. ; _publ_section_comment ; The crystal is twinned. The structure could be solved by direct methods using the raw data and assuming no twinning, but would not refine below 10%. The constrained least squares refinement program RAELS2000 can account for twinning, pseudo-symmetry and stacking faults and was ideal for refining this structure. In the crystallographic asymmetric unit there are three C~16~H~26~O~6~ molecules which are chemically identical and pseudo-symmetrically related. The crystal was a 0.716(2) : 0.284 twin and also had a stacking fault so that reflections with h - k \\neq 3N had F~calc~ scaled by 0.912(3) compared to reflections with h - k = 3N. Also 0.011(1) of the structure is a disorder created by the same pseudo symmetry operator as the observed twin rule that relates the hkl and -k-h-l reflections. Full details of the refinement procedure are given in the accompanying report and in _refine_special_details of the crystallographic information file (CIF). There were no outstanding features in the final difference electron density map. ; _publ_section_exptl_prep ; The compound was prepared by DTL and recrystallized from isopropanol/dichloromethane. The sample ID is DTLRCMA. ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; Hydrogen atoms coordinates were refined with constraints and given atomic displacement parameters determined by the atoms to which they are attached. ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; _refine_special_details ; MGB045 C16H26O6 a = b 18.6850(2), c 12.2359(1) \%A, a 90, b 90, g 120 \%. Space group P31 Z = 9 The constrained least squares refinement program RAELS2000 was used for refinement. The crystal studied was a 0.716(2) : 0.284 twin and also had a stacking fault so that reflections with h - k \\neq 3N had Fcalc scaled by 0.912(3) compared to reflections with h - k = 3N. Also 0.011(1) of the structure is a disorder created by the same pseudo symmetry operator as the observed twin rule that relates the hkl and -k-h-l reflections. The structure contains three columns of 31 symmetry in the unit cell along 1/3,2/3,z; 1,1, z; and 2/3,1/3,z related by the pseudo symmetry operation 5/3-y,4/3-x,1-z. The structure can be described as an occupancy ordering of a 1:1 disordered parent structure in space group P3121 with one third the cell volume and Z = 3. A 2 fold axis is the disordering operation and the origin can be chosen so that this 2 fold axis passes through it. Ordering allows each column to take up one of the two orientations related by this two fold axis perpendicular to c. The resulting structure contains a pseudo two fold screw axis 5/3-y, 4/3-x, 1-z relating the three moleculues in the asymmetric unit of P31. The atoms O17, O117, O217 lie approximately on this screw axis. The ordered structure has two columns in one orientation and the other column is in the alternative orientation. This creates diffraction symmetry enhancement without twinning for the h - k \\neq 3N reflections should the pseudo 2 fold screw axis operations hold exactly. The 2 : 1 ratio of columns in different orientations must be compromised in a twin disorder mechanism to explain the final refinement model which scaled the h- k \\neq 3N reflections relative to the h- k = 3N reflections and applied a twin-disorder rule relating the hkl and -k-h-l reflection intensities. Various constraints were used in refinement to reduce the number of variables and allow the H atoms to be refined. Pseudo screw axis related O---Me and C---Me atom groups were constrained to have identical refineable geometries of exact local 3m symmetry using refinable local orthonormal axial systems and refineable local orthoonormal axial systems (Rae, 1975). Non pseudo equivalent O---C and C---C distances were allowed to be independent. However only two sets of local coordinates were used for the methyl Hydrogens, one set for all methyls attached to an O atom, the other for the methyls attached to a C atom. All non H atoms had independent anisotropic atom displacement parameters and the H atoms were constrained to have the same parameters as the atom to which they were attached. Three sets of methyl Hydrogens, those attached to O20, O120 and O220 were allowed an extra common libration about the relevant C-H bond that was common to all 3 sets. These constraints allowed an essentially anisotropic refinement of all atoms using 707 variables for a reflection set of 5022 independent reflections with I >3\s(I) obtained after merging assuming P-3 diffraction symmetry. The twinning reduced the difference between twin related reflection intensities by a factor of 0.432 compared to an untwinned crystal. The Rmerge for P-3 was 0.055 compared to 0.114 for P-31m diffraction symmetry. Data sets were collected for three different crystals and the crystal chosen for refinement was the one that had the best Rmerge for P-3 but the worst for P-31m. An initial structure solution was obtained by direct methods using SIR97 and space group P31. The handedness of the molecule was known and P31 rather than the inverted structure in P32 is appropriate. Effect on Intensities of stacking faults The structure can be described as three pseudosymmetry related columns as described above. The columns at 1/3,2/3,z amd 2/3,1/3,z are related by the translation 1/3(a - b). If we say F1(h) is the stucture factor for a column at the origin and if we choose the origin along c so that a 2 fold rotation through the origin creates the alternative orientation for each column, then assuming only an occupancy modulation of a 1:1 disordered parent structure F(h) = [(1-p1) + \w (1-p2) + \w* (1-p3)]F1(h) + [p1 + \w p2 + \w* p3]F1(2h) where \w = exp(2\pi(h-k)/3) and (1-pj): pj gives the population ratio for the alternative orientations of a column. The perfectly ordered structure corresponding to our listed coordinates has p1, p2, p3 = 0,1,1. Values for p1, p2, p3 of 1,0,1 and 1,1,0 correspond to different origin choices. Structures related by a 2 fold rotation through the origin are obtained by swapping the values of (1-pj) and pj. Translational stacking faults of layers would preserve the value of p1 + p2 + p3. When h - k \\neq 3N F(h) = [p1 + \w p2 + \w* p3][F1(2h) - F1(h)] and F(2h) = [p1 + \w* p2 + \w p3][F1(h) - F1(2h)] so that I(h) = I(2h) = [p12 + p22 + p32 - p1p2 - p2p3 - p3p1]|F1(h) - F1(2h)|2. For a perfectly ordered structure I(h) = I(2h) = |F1(h) - F1(2h)|2 and F(h) = - F(2h). It is possible to have diffraction symmetry enhancement and scaling without the need for twinning to describe these reflections should the pseudo symmetry operations hold exactly. When h - k = 3N F(h) = 3/2[F1(h) + F1(2h)] + [p1 + p2 + p3 - 3/2][F1(2h) - F1(h)] and F(2h) = 3/2[F1(h) + F1(2h)] - [p1 + p2 + p3 - 3/2][F1(2h) - F1(h)] so that [I(h) + I(2h)]/2 = 9/4|F1(h) + F1(2h)|2 + [p1 + p2 + p3 - 3/2]2 |F1(2h) - F1(h)|2 and [I(h) - I(2h)]/2 = 6 [p1 + p2 + p3 - 3/2] [|F1(2h)|2 - |F1(h)|2]. If we preserve the value of p1 + p2 + p3 as 2 then F(h) = [F1(h) + 2 F1(2h)] and F(2h) = [2 F1(h) + F1(2h)] so that [I(h) + I(2h)]/2 = 9/4 |F1(h) + F1(2h)|2 + 1/4 |F1(2h) - F1(h)|2 and I(h) - I(2h)]/2 = +- 3 [|F1(2h)|2 - |F1(h)|2]. Our first model refined a twin ratio (1-q) : q where q = 0.283(2) and a separate scale for h - k \\neq 3N reflections. The twinning to multiply I(h) - I(2h)]/2 by 1 - 2q = 0.434(4) rather than 1.0 implies a two fold screw axis perpendicular to c must be involved in creating a truly twin- disorder structure. The scaling of h - k \\neq 3N reflection amplitudes by 0.896(3) would imply the value of [p12 + p22 + p32 - p1p2 - p2p3 - p3p1] = 0.803(6), ie 0.8962, when averaged over twin related mosaic blocks. This is capable of many solutions and offers no further information. This refinement assumed that p1 + p2 + p3 = 2 and makes 1/4|F1(2h) - F1(h)]|2 to be just 10% of [I(h) + I(2h)]/2 on average. Any disorder will probably make [p1 + p2 + p3 - 3/2]2 tend to zero. This model is refineable and was achieved using the model I(h) = (1-q)[(1-p) F(h) + p F(2h)]2 + q[(1-p) F(2h) + p F(h)]2, where disorder parameter p and the twin parameter q are refinable using RAELS2000. If we no longer use two scales we imply that there are no translational stacking faults. Such a refinement improves the data fit for h - k = 3N but makes it worse for h - k 3N and suggested that both types of stacking faults are present and two scales should still be used. This final model refined successfully and gave the results described in the summary at the beginning of this report. References (1) RAELS2000, A.D. Rae (2000) Australian National University, Canberra, Australia. (2) Rae, A.D. (1975) Acta Cryst. A31, 560-570, 570-574. Table 1. Refinement Statistics. Class** Number R(F) R(F2) wR Gof 1 1702 0.035 0.059 0.047 1.346 2 3320 0.040 0.073 0.048 1.264 1-2 5022 0.038 0.065 0.048 1.292 3 607 0.210 0.386 0.248 1.072 1-3 5629 0.043 0.066 0.050 1.281 An uncorrelated 3% error in |F(h)| was included along with counting statistic error for evaluating weights w = 1/(\s(F)2 + (0.03F)2). Refinement was on F. Index 1 Reflections with I > 3\s(I) and h - k = 3N Index 2 Reflections with I > 3\s(I) and h - k \\neq 3N Index 3 Reflections with I < 3\s(I). The refinement used 707 variables for 66 non H atoms and 78 H atoms. Residual electron density, minimum -0.230 e \%A-3, maximum 0.255 e \%A-3. In the final full matrix refinement cycle no parameter shifts were greater than 0.1 sigma. ; _chemical_compound_source 'Local laboratory' _exptl_crystal_description prism _exptl_crystal_colour Colourless _exptl_crystal_size_min 0.28 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_max 0.47 _cell_measurement_temperature 200 _refine_ls_hydrogen_treatment constr _diffrn_measurement_device_type ; Enraf Nonius Kappa CCD ; _diffrn_radiation_monochromator graphite _diffrn_measurement_method ' \f and \w scans with CCD ' _diffrn_special_details ; CCD data collecting conditions- phi and omega scans of width 2.0 deg at rate 80 sec/frame, crystal-detector distance 32mm, multiple scan sets so over 95 percent of data collected with 4-fold redundancy or more. ; _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _computing_data_collection ; COLLECT (Nonius BV, 1997) ; _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_number 98252 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_full 27.49 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type X=UH _diffrn_orient_matrix_UB_11 -0.04581 _diffrn_orient_matrix_UB_12 -0.03903 _diffrn_orient_matrix_UB_13 0.01405 _diffrn_orient_matrix_UB_21 0.01085 _diffrn_orient_matrix_UB_22 -0.04840 _diffrn_orient_matrix_UB_23 0.03686 _diffrn_orient_matrix_UB_31 -0.01871 _diffrn_orient_matrix_UB_32 0.04542 _diffrn_orient_matrix_UB_33 0.06516 _cell_formula_units_Z 9 _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 314.378 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -y,x-y,1/3+z 3 -x+y,-x,2/3+z _symmetry_space_group_name_H-M 'P 31 ' _symmetry_cell_setting Trigonal _chemical_formula_moiety 'C16 H26 O6 ' _chemical_formula_sum 'C16 H26 O6 ' _chemical_name_systematic ; ? ; _cell_length_a 18.6850(2) _cell_length_b 18.6850(2) _cell_length_c 12.25390(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3705.02(6) _cell_measurement_reflns_used 84318 _cell_measurement_theta_min 2.546 _cell_measurement_theta_max 27.485 _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_av_R_equivalents 0.055 # Dave's _computing_structure_solution 'SIR97(Cascarano al.,Acta Cryst.,1996,A52,C-79)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 1 1 0.160 -1 -1 -1 0.160 2 -1 -1 0.100 -2 1 1 0.180 -3 5 -2 0.243 3 -5 2 0.231 1 -2 0 0.135 -1 2 0 0.298 17 -6 1 0.148 -2 -4 0 0.172 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.963 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; _exptl_absorpt_coefficient_mu 0.096 _exptl_crystal_F_000 1530 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C ' 'C ' 0.0033 0.0016 International_Tables_Vol_IV_Table_2.2A 'H ' 'H ' 0.0000 0.0000 International_Tables_Vol_IV_Table_2.2A 'O ' 'O ' 0.0106 0.0060 International_Tables_Vol_IV_Table_2.2A # Refinement statistics # 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 syn _refine_ls_abs_structure_details ; The enantiomer has been assigned by reference to an unchanging chiral centre in the synthetic procedure. ; _reflns_d_resolution_low 1.93 _reflns_d_resolution_high 0.62 _reflns_limit_h_max 24 _reflns_limit_h_min 0 _reflns_limit_k_max 0 _reflns_limit_k_min -20 _reflns_limit_l_max 15 _reflns_limit_l_min -15 _refine_ls_matrix_type full _refine_ls_shift/su_max .1 _reflns_number_total 5629 # Dave's _refine_ls_R_factor_all 0.043 _refine_ls_wR_factor_all 0.050 _refine_ls_goodness_of_fit_all 1.281 _reflns_number_gt 5022 _reflns_threshold_expression 'I> 3.00 \s(I)' _refine_ls_R_factor_gt 0.038 _refine_ls_wR_factor_gt 0.048 _refine_ls_goodness_of_fit_gt 1.292 _refine_ls_number_reflns 5022 _refine_ls_number_parameters 707 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_wR_factor_ref 0.048 _refine_ls_goodness_of_fit_ref 1.292 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme sigma _refine_ls_weighting_details ; w = 1 / ( \s^2^(Fo^2^) + 0.0009 \\times Fo^2^) ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _computing_structure_refinement 'RAELS2000 (Rae 2000)' _computing_molecular_graphics ; ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) ; _computing_publication_material 'maXus(Mackay et al., 1999)' _atom_sites_solution_hydrogens geom _refine_diff_density_max .255 _refine_diff_density_min -.230 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Rae, A. D., RAELS2000, Australian National University, Canberra, Australia. Rae, A.D. (1975) Acta Cryst. A31, 560-570, 570-574. COLLECT Software, Nonius BV 1997-2001) Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (2000). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Coppens, P. (1970). The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed, S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A.A.G., Polidori, G. & Spagna, R. (1999) SIR97 - a new tool for crystal structure determination and refinement. J. Appl. Cryst,. 32, 115-119. Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Johnson, C.K. (1976) ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. ; #================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_refinement_flags _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom C1 0.5333(2) 0.7476(2) 0.7351(3) 1.0 0.030(1) . Uani d ? C2 0.5201(2) 0.7819(2) 0.6298(3) 1.0 0.028(1) . Uani d ? C3 0.4439(2) 0.7172(2) 0.5690(3) 1.0 0.034(1) . Uani d ? C4 0.4518(3) 0.6446(2) 0.5272(3) 1.0 0.040(1) . Uani d ? C5 0.4288(2) 0.5755(2) 0.6120(4) 1.0 0.043(1) . Uani d ? C6 0.4890(2) 0.5445(2) 0.6155(3) 1.0 0.040(1) . Uani d ? C7 0.5372(3) 0.5514(2) 0.6976(3) 1.0 0.042(1) . Uani d ? C8 0.5417(3) 0.5924(2) 0.8055(3) 1.0 0.039(1) . Uani d ? C9 0.6065(2) 0.6835(2) 0.8095(3) 1.0 0.035(1) . Uani d ? O10 0.5922(1) 0.7273(1) 0.7201(2) 1.0 0.032(1) . Uani d ? C11 0.6940(2) 0.7007(2) 0.7925(2) 1.0 0.046(1) . Uani d ? O12 0.4962(2) 0.7379(2) 0.8193(2) 1.0 0.041(1) . Uani d ? O13 0.5108(2) 0.8510(1) 0.6597(2) 1.0 0.032(1) . Uani d ? C14 0.5000(2) 0.8912(2) 0.5670(3) 1.0 0.032(1) . Uani d ? C15 0.4268(2) 0.8276(2) 0.4959(2) 1.0 0.036(1) . Uani d ? O16 0.4357(2) 0.7580(2) 0.4735(2) 1.0 0.036(1) . Uani d ? O17 0.5705(2) 0.9219(2) 0.4981(2) 1.0 0.037(1) . Uani d ? C18 0.6455(2) 0.9896(2) 0.5388(2) 1.0 0.046(1) . Uani d ? C19 0.4875(2) 0.9593(2) 0.6139(2) 1.0 0.042(1) . Uani d ? O20 0.3561(2) 0.8059(2) 0.5607(2) 1.0 0.044(1) . Uani d ? C21 0.2795(2) 0.7425(2) 0.5179(2) 1.0 0.065(1) . Uani d ? C22 0.4232(3) 0.8616(2) 0.3849(2) 1.0 0.047(1) . Uani d ? C101 0.9251(2) 0.8018(2) 0.2630(3) 1.0 0.025(1) . Uani d ? C102 0.8876(2) 0.8142(2) 0.3666(3) 1.0 0.026(1) . Uani d ? C103 0.9500(2) 0.8900(2) 0.4312(3) 1.0 0.028(1) . Uani d ? C104 1.0222(2) 0.8817(3) 0.4757(3) 1.0 0.037(1) . Uani d ? C105 1.0937(2) 0.9088(2) 0.3926(3) 1.0 0.037(1) . Uani d ? C106 1.1278(2) 0.8510(3) 0.3898(3) 1.0 0.040(1) . Uani d ? C107 1.1236(2) 0.8033(3) 0.3059(3) 1.0 0.038(1) . Uani d ? C108 1.0837(2) 0.8000(3) 0.1978(3) 1.0 0.037(1) . Uani d ? C109 0.9935(2) 0.7323(2) 0.1921(3) 1.0 0.032(1) . Uani d ? O110 0.9477(1) 0.7459(1) 0.2797(2) 1.0 0.026(1) . Uani d ? C111 0.9791(2) 0.6458(2) 0.2084(2) 1.0 0.044(1) . Uani d ? O112 0.9339(2) 0.8394(2) 0.1797(2) 1.0 0.036(1) . Uani d ? O113 0.8187(1) 0.8225(1) 0.3357(2) 1.0 0.026(1) . Uani d ? C114 0.7765(2) 0.8323(2) 0.4267(3) 1.0 0.031(1) . Uani d ? C115 0.8387(2) 0.9067(2) 0.4980(2) 1.0 0.033(1) . Uani d ? O116 0.9079(2) 0.8980(2) 0.5235(2) 1.0 0.034(1) . Uani d ? O117 0.7472(2) 0.7641(2) 0.4979(2) 1.0 0.039(1) . Uani d ? C118 0.6873(2) 0.6869(2) 0.4517(2) 1.0 0.053(1) . Uani d ? C119 0.7088(2) 0.8449(3) 0.3785(2) 1.0 0.041(1) . Uani d ? O120 0.8618(2) 0.9763(1) 0.4304(2) 1.0 0.040(1) . Uani d ? C121 0.9230(3) 1.0541(2) 0.4726(2) 1.0 0.063(1) . Uani d ? C122 0.8034(2) 0.9118(3) 0.6073(2) 1.0 0.046(1) . Uani d ? C201 0.8612(2) 0.3993(2) 0.7394(3) 1.0 0.029(1) . Uani d ? C202 0.8528(2) 0.4383(2) 0.6357(3) 1.0 0.028(1) . Uani d ? C203 0.7752(2) 0.3781(2) 0.5720(3) 1.0 0.031(1) . Uani d ? C204 0.7781(2) 0.3038(2) 0.5284(3) 1.0 0.038(1) . Uani d ? C205 0.7447(2) 0.2312(2) 0.6091(3) 1.0 0.038(1) . Uani d ? C206 0.7975(2) 0.1912(2) 0.6142(3) 1.0 0.037(1) . Uani d ? C207 0.8427(2) 0.1922(2) 0.6981(3) 1.0 0.036(1) . Uani d ? C208 0.8485(2) 0.2331(2) 0.8054(3) 1.0 0.037(1) . Uani d ? C209 0.9209(2) 0.3215(2) 0.8123(3) 1.0 0.032(1) . Uani d ? O210 0.9150(1) 0.3718(1) 0.7240(2) 1.0 0.030(1) . Uani d ? C211 1.0038(2) 0.3268(2) 0.7968(2) 1.0 0.043(1) . Uani d ? O212 0.8242(2) 0.3906(2) 0.8230(2) 1.0 0.041(1) . Uani d ? O213 0.8483(2) 0.5093(1) 0.6679(2) 1.0 0.032(1) . Uani d ? C214 0.8431(2) 0.5539(2) 0.5760(3) 1.0 0.035(1) . Uani d ? C215 0.7677(2) 0.4951(2) 0.5051(2) 1.0 0.037(1) . Uani d ? O216 0.7706(2) 0.4227(2) 0.4788(2) 1.0 0.035(1) . Uani d ? O217 0.9128(2) 0.5789(2) 0.5067(2) 1.0 0.043(1) . Uani d ? C218 0.9918(2) 0.6333(2) 0.5535(2) 1.0 0.056(1) . Uani d ? C219 0.8382(3) 0.6261(2) 0.6241(2) 1.0 0.047(1) . Uani d ? O220 0.6983(2) 0.4764(2) 0.5704(2) 1.0 0.044(1) . Uani d ? C221 0.6198(2) 0.4183(2) 0.5263(2) 1.0 0.062(1) . Uani d ? C222 0.7663(3) 0.5326(2) 0.3958(2) 1.0 0.050(1) . Uani d ? H2 0.5723(34) 0.8081(31) 0.5862(41) 1.0 0.039(1) . Uani d ? H3 0.3861(32) 0.6993(29) 0.6206(37) 1.0 0.035(1) . Uani d ? H4A 0.4250(29) 0.6255(29) 0.4602(39) 1.0 0.032(1) . Uani d ? H4B 0.5092(30) 0.6710(29) 0.4968(39) 1.0 0.032(1) . Uani d ? H5A 0.4295(34) 0.5962(34) 0.6896(46) 1.0 0.046(1) . Uani d ? H5B 0.3622(33) 0.5265(31) 0.5914(43) 1.0 0.046(1) . Uani d ? H6 0.4857(34) 0.5199(35) 0.5437(43) 1.0 0.041(1) . Uani d ? H7 0.5669(30) 0.5187(30) 0.6820(37) 1.0 0.032(1) . Uani d ? H8A 0.4858(29) 0.5886(28) 0.8265(38) 1.0 0.032(1) . Uani d ? H8B 0.5516(29) 0.5687(28) 0.8726(38) 1.0 0.032(1) . Uani d ? H9 0.6010(30) 0.7063(31) 0.8776(41) 1.0 0.036(1) . Uani d ? H11A 0.7068(9) 0.6693(16) 0.8451(17) 1.0 0.036(1) . Uani d ? H11B 0.7331(6) 0.7596(7) 0.8024(25) 1.0 0.036(1) . Uani d ? H11C 0.7002(8) 0.6846(18) 0.7187(11) 1.0 0.036(1) . Uani d ? H18A 0.6916(8) 0.9954(13) 0.4938(17) 1.0 0.042(1) . Uani d ? H18B 0.6528(11) 0.9781(11) 0.6149(12) 1.0 0.042(1) . Uani d ? H18C 0.6415(10) 1.0400(8) 0.5345(23) 1.0 0.042(1) . Uani d ? H19A 0.4881(21) 0.9952(13) 0.5555(8) 1.0 0.044(1) . Uani d ? H19B 0.5317(12) 0.9926(13) 0.6656(21) 1.0 0.044(1) . Uani d ? H19C 0.4345(11) 0.9354(6) 0.6519(24) 1.0 0.044(1) . Uani d ? H21A 0.2361(8) 0.7292(20) 0.5724(17) 1.0 0.069(6) . Uani d ? H21B 0.2846(11) 0.6937(11) 0.5025(33) 1.0 0.066(2) . Uani d ? H21C 0.2672(15) 0.7628(12) 0.4505(20) 1.0 0.067(2) . Uani d ? H22A 0.4165(23) 0.9099(15) 0.3934(8) 1.0 0.047(1) . Uani d ? H22B 0.3766(14) 0.8196(10) 0.3429(13) 1.0 0.047(1) . Uani d ? H22C 0.4743(11) 0.8779(21) 0.3445(14) 1.0 0.047(1) . Uani d ? H102 0.8721(31) 0.7675(33) 0.4086(38) 1.0 0.037(1) . Uani d ? H103 0.9683(30) 0.9372(29) 0.3833(39) 1.0 0.032(1) . Uani d ? H104A 1.0480(26) 0.9219(28) 0.5380(40) 1.0 0.026(1) . Uani d ? H104B 1.0056(27) 0.8207(29) 0.4960(35) 1.0 0.026(1) . Uani d ? H105A 1.0760(34) 0.9168(32) 0.3175(47) 1.0 0.044(1) . Uani d ? H105B 1.1291(35) 0.9552(35) 0.4107(44) 1.0 0.044(1) . Uani d ? H106 1.1550(31) 0.8490(31) 0.4584(41) 1.0 0.036(1) . Uani d ? H107 1.1486(27) 0.7616(28) 0.3018(35) 1.0 0.026(1) . Uani d ? H108A 1.0875(29) 0.8559(31) 0.1842(37) 1.0 0.031(1) . Uani d ? H108B 1.1151(29) 0.7912(29) 0.1432(37) 1.0 0.031(1) . Uani d ? H109 0.9645(30) 0.7359(29) 0.1212(39) 1.0 0.033(1) . Uani d ? H111A 1.0110(15) 0.6343(8) 0.1552(17) 1.0 0.034(1) . Uani d ? H111B 0.9204(6) 0.6053(6) 0.1992(23) 1.0 0.034(1) . Uani d ? H111C 0.9961(17) 0.6401(8) 0.2819(11) 1.0 0.034(1) . Uani d ? H118A 0.6750(15) 0.6429(7) 0.5049(13) 1.0 0.041(1) . Uani d ? H118B 0.7102(10) 0.6775(11) 0.3846(15) 1.0 0.041(1) . Uani d ? H118C 0.6371(9) 0.6893(10) 0.4352(24) 1.0 0.041(1) . Uani d ? H119A 0.6745(13) 0.8478(20) 0.4367(8) 1.0 0.040(1) . Uani d ? H119B 0.6738(13) 0.7989(11) 0.3300(21) 1.0 0.040(1) . Uani d ? H119C 0.7331(6) 0.8963(11) 0.3366(22) 1.0 0.040(1) . Uani d ? H121A 0.9403(20) 1.0956(9) 0.4143(13) 1.0 0.066(6) . Uani d ? H121B 0.9703(13) 1.0493(10) 0.4978(32) 1.0 0.064(2) . Uani d ? H121C 0.8991(11) 1.0691(14) 0.5337(24) 1.0 0.065(2) . Uani d ? H122A 0.7569(15) 0.9212(23) 0.5964(8) 1.0 0.046(1) . Uani d ? H122B 0.8457(9) 0.9573(15) 0.6505(14) 1.0 0.046(1) . Uani d ? H122C 0.7840(21) 0.8602(10) 0.6477(14) 1.0 0.046(1) . Uani d ? H202 0.9012(33) 0.4602(30) 0.5907(40) 1.0 0.037(1) . Uani d ? H203 0.7276(30) 0.3645(29) 0.6200(39) 1.0 0.032(1) . Uani d ? H204A 0.7539(29) 0.2901(28) 0.4567(40) 1.0 0.030(1) . Uani d ? H204B 0.8375(30) 0.3199(28) 0.5131(37) 1.0 0.030(1) . Uani d ? H205A 0.7449(33) 0.2518(34) 0.6916(44) 1.0 0.043(1) . Uani d ? H205B 0.6842(33) 0.1925(34) 0.5933(42) 1.0 0.043(1) . Uani d ? H206 0.7932(32) 0.1556(32) 0.5490(40) 1.0 0.041(1) . Uani d ? H207 0.8877(29) 0.1676(28) 0.6809(34) 1.0 0.032(1) . Uani d ? H208A 0.7945(31) 0.2369(29) 0.8244(38) 1.0 0.035(1) . Uani d ? H208B 0.8605(30) 0.2082(29) 0.8719(37) 1.0 0.035(1) . Uani d ? H209 0.9198(31) 0.3507(31) 0.8831(41) 1.0 0.037(1) . Uani d ? H211A 1.0081(9) 0.2871(14) 0.8443(19) 1.0 0.035(1) . Uani d ? H211B 1.0485(6) 0.3823(8) 0.8147(24) 1.0 0.035(1) . Uani d ? H211C 1.0101(10) 0.3145(19) 0.7210(9) 1.0 0.035(1) . Uani d ? H218A 1.0347(7) 0.6337(16) 0.5066(16) 1.0 0.047(1) . Uani d ? H218B 0.9940(10) 0.6130(13) 0.6266(13) 1.0 0.047(1) . Uani d ? H218C 0.9990(11) 0.6889(8) 0.5581(24) 1.0 0.047(1) . Uani d ? H219A 0.8344(21) 0.6598(13) 0.5657(8) 1.0 0.044(1) . Uani d ? H219B 0.8874(11) 0.6607(12) 0.6678(22) 1.0 0.044(1) . Uani d ? H219C 0.7894(12) 0.6060(6) 0.6707(22) 1.0 0.044(1) . Uani d ? H221A 0.5780(8) 0.4017(20) 0.5840(13) 1.0 0.065(6) . Uani d ? H221B 0.6224(11) 0.3701(13) 0.4996(31) 1.0 0.063(2) . Uani d ? H221C 0.6070(13) 0.4447(11) 0.4659(23) 1.0 0.063(2) . Uani d ? H222A 0.7622(23) 0.5823(14) 0.4069(8) 1.0 0.050(1) . Uani d ? H222B 0.7188(14) 0.4929(10) 0.3528(14) 1.0 0.050(1) . Uani d ? H222C 0.8169(12) 0.5475(21) 0.3552(14) 1.0 0.050(1) . Uani d ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.035(2) 0.024(2) 0.033(2) 0.016(1) 0.000(1) -0.001(1) C2 0.034(2) 0.025(2) 0.030(2) 0.018(1) -0.001(1) -0.003(1) C3 0.038(2) 0.033(2) 0.032(2) 0.018(2) -0.002(1) 0.006(1) C4 0.052(2) 0.031(2) 0.038(2) 0.021(2) -0.006(2) -0.001(2) C5 0.041(2) 0.028(2) 0.054(2) 0.013(2) -0.008(2) 0.002(2) C6 0.048(2) 0.024(2) 0.045(2) 0.015(2) -0.003(2) -0.003(2) C7 0.056(2) 0.030(2) 0.043(2) 0.023(2) -0.003(2) -0.001(2) C8 0.054(2) 0.035(2) 0.032(2) 0.026(2) -0.001(2) 0.003(1) C9 0.050(2) 0.036(2) 0.026(2) 0.027(2) -0.009(2) 0.001(1) O10 0.036(1) 0.033(1) 0.031(1) 0.020(1) -0.003(1) 0.002(1) C11 0.050(2) 0.047(2) 0.047(2) 0.029(2) -0.007(2) 0.003(2) O12 0.053(2) 0.053(2) 0.032(1) 0.036(1) 0.007(1) 0.006(1) O13 0.043(1) 0.030(1) 0.031(1) 0.023(1) 0.000(1) 0.003(1) C14 0.038(2) 0.033(2) 0.031(2) 0.021(2) 0.000(1) 0.004(1) C15 0.042(2) 0.039(2) 0.034(2) 0.025(2) -0.003(1) 0.004(1) O16 0.044(1) 0.035(1) 0.032(1) 0.022(1) -0.005(1) 0.001(1) O17 0.036(1) 0.033(1) 0.040(1) 0.015(1) 0.004(1) 0.008(1) C18 0.043(2) 0.043(2) 0.051(2) 0.021(2) -0.002(2) -0.002(2) C19 0.059(2) 0.042(2) 0.041(2) 0.038(2) 0.002(2) 0.006(2) O20 0.036(1) 0.052(2) 0.046(2) 0.023(1) -0.002(1) 0.005(1) C21 0.037(2) 0.071(3) 0.079(3) 0.021(2) -0.009(2) 0.013(3) C22 0.056(2) 0.051(2) 0.041(2) 0.032(2) -0.007(2) 0.005(2) C101 0.027(2) 0.028(2) 0.021(2) 0.014(1) -0.002(1) -0.004(1) C102 0.026(2) 0.029(2) 0.024(2) 0.013(1) 0.005(1) 0.001(1) C103 0.030(2) 0.031(2) 0.024(2) 0.016(1) -0.003(1) -0.003(1) C104 0.033(2) 0.051(2) 0.029(2) 0.022(2) -0.006(1) -0.010(2) C105 0.028(2) 0.035(2) 0.040(2) 0.009(2) -0.003(2) -0.008(2) C106 0.028(2) 0.051(2) 0.038(2) 0.019(2) -0.004(2) -0.003(2) C107 0.031(2) 0.047(2) 0.038(2) 0.021(2) 0.000(1) 0.002(2) C108 0.032(2) 0.053(2) 0.030(2) 0.025(2) 0.004(1) 0.000(2) C109 0.036(2) 0.040(2) 0.028(2) 0.025(2) 0.002(1) -0.002(1) O110 0.026(1) 0.029(1) 0.026(1) 0.016(1) 0.001(1) 0.000(1) C111 0.057(2) 0.040(2) 0.049(2) 0.034(2) -0.001(2) -0.008(2) O112 0.046(1) 0.047(2) 0.024(1) 0.031(1) 0.004(1) 0.006(1) O113 0.025(1) 0.034(1) 0.022(1) 0.016(1) 0.000(1) -0.002(1) C114 0.031(2) 0.040(2) 0.027(2) 0.020(2) 0.008(1) 0.001(1) C115 0.042(2) 0.040(2) 0.024(2) 0.027(2) 0.004(1) -0.002(1) O116 0.041(1) 0.041(1) 0.025(1) 0.024(1) -0.001(1) -0.008(1) O117 0.044(2) 0.037(1) 0.032(1) 0.016(1) 0.011(1) 0.008(1) C118 0.037(2) 0.038(2) 0.071(3) 0.008(2) 0.004(2) 0.000(2) C119 0.037(2) 0.055(2) 0.043(2) 0.031(2) 0.004(2) -0.001(2) O120 0.053(2) 0.034(1) 0.038(1) 0.025(1) 0.002(1) 0.002(1) C121 0.088(4) 0.036(2) 0.060(3) 0.027(2) 0.006(3) -0.009(2) C122 0.061(3) 0.067(3) 0.025(2) 0.043(2) 0.007(2) -0.005(2) C201 0.033(2) 0.023(2) 0.032(2) 0.015(1) 0.000(1) 0.002(1) C202 0.034(2) 0.028(2) 0.028(2) 0.019(1) -0.001(1) 0.000(1) C203 0.033(2) 0.035(2) 0.027(2) 0.018(2) -0.005(1) 0.001(1) C204 0.044(2) 0.035(2) 0.034(2) 0.020(2) -0.001(2) -0.002(1) C205 0.034(2) 0.029(2) 0.048(2) 0.013(2) -0.006(2) 0.000(2) C206 0.041(2) 0.027(2) 0.036(2) 0.013(2) 0.000(1) -0.004(1) C207 0.045(2) 0.027(2) 0.035(2) 0.018(2) 0.003(2) 0.005(1) C208 0.048(2) 0.033(2) 0.032(2) 0.023(2) 0.006(2) 0.006(1) C209 0.042(2) 0.031(2) 0.030(2) 0.024(2) -0.006(1) 0.003(1) O210 0.032(1) 0.032(1) 0.032(1) 0.020(1) 0.000(1) 0.004(1) C211 0.047(2) 0.047(2) 0.043(2) 0.029(2) -0.006(2) 0.004(2) O212 0.059(2) 0.050(2) 0.030(1) 0.038(1) 0.010(1) 0.007(1) O213 0.042(1) 0.032(1) 0.028(1) 0.023(1) 0.000(1) 0.003(1) C214 0.046(2) 0.034(2) 0.030(2) 0.024(2) 0.007(1) 0.010(1) C215 0.048(2) 0.046(2) 0.029(2) 0.033(2) 0.003(1) 0.006(1) O216 0.045(1) 0.042(1) 0.026(1) 0.028(1) -0.004(1) 0.001(1) O217 0.049(2) 0.044(2) 0.035(1) 0.022(1) 0.007(1) 0.011(1) C218 0.047(2) 0.054(3) 0.059(3) 0.019(2) 0.005(2) 0.011(2) C219 0.075(3) 0.044(2) 0.038(2) 0.042(2) -0.001(2) 0.008(2) O220 0.040(1) 0.060(2) 0.040(1) 0.031(1) -0.001(1) 0.002(1) C221 0.044(2) 0.074(3) 0.068(3) 0.030(2) -0.005(2) 0.001(3) C222 0.070(3) 0.059(3) 0.036(2) 0.044(2) -0.006(2) 0.004(2) H2 0.054(2) 0.035(2) 0.032(2) 0.026(2) -0.001(2) 0.003(1) H3 0.050(2) 0.036(2) 0.026(2) 0.027(2) -0.009(2) 0.001(1) H4A 0.036(1) 0.033(1) 0.031(1) 0.020(1) -0.003(1) 0.002(1) H4B 0.036(1) 0.033(1) 0.031(1) 0.020(1) -0.003(1) 0.002(1) H5A 0.050(2) 0.047(2) 0.047(2) 0.029(2) -0.007(2) 0.003(2) H5B 0.050(2) 0.047(2) 0.047(2) 0.029(2) -0.007(2) 0.003(2) H6 0.053(2) 0.053(2) 0.032(1) 0.036(1) 0.007(1) 0.006(1) H7 0.043(1) 0.030(1) 0.031(1) 0.023(1) 0.000(1) 0.003(1) H8A 0.038(2) 0.033(2) 0.031(2) 0.021(2) 0.000(1) 0.004(1) H8B 0.038(2) 0.033(2) 0.031(2) 0.021(2) 0.000(1) 0.004(1) H9 0.042(2) 0.039(2) 0.034(2) 0.025(2) -0.003(1) 0.004(1) H11A 0.044(1) 0.035(1) 0.032(1) 0.022(1) -0.005(1) 0.001(1) H11B 0.044(1) 0.035(1) 0.032(1) 0.022(1) -0.005(1) 0.001(1) H11C 0.044(1) 0.035(1) 0.032(1) 0.022(1) -0.005(1) 0.001(1) H18A 0.059(2) 0.042(2) 0.041(2) 0.038(2) 0.002(2) 0.006(2) H18B 0.059(2) 0.042(2) 0.041(2) 0.038(2) 0.002(2) 0.006(2) H18C 0.059(2) 0.042(2) 0.041(2) 0.038(2) 0.002(2) 0.006(2) H19A 0.036(1) 0.052(2) 0.046(2) 0.023(1) -0.002(1) 0.005(1) H19B 0.036(1) 0.052(2) 0.046(2) 0.023(1) -0.002(1) 0.005(1) H19C 0.036(1) 0.052(2) 0.046(2) 0.023(1) -0.002(1) 0.005(1) H21A 0.041(8) 0.077(10) 0.083(6) 0.026(9) -0.005(7) 0.018(8) H21B 0.039(3) 0.072(3) 0.081(5) 0.022(3) -0.011(4) 0.012(4) H21C 0.042(8) 0.076(9) 0.079(3) 0.025(8) -0.008(2) 0.014(3) H22A 0.056(2) 0.051(2) 0.041(2) 0.032(2) -0.007(2) 0.005(2) H22B 0.056(2) 0.051(2) 0.041(2) 0.032(2) -0.007(2) 0.005(2) H22C 0.056(2) 0.051(2) 0.041(2) 0.032(2) -0.007(2) 0.005(2) H102 0.032(2) 0.053(2) 0.030(2) 0.025(2) 0.004(1) 0.000(2) H103 0.036(2) 0.040(2) 0.028(2) 0.025(2) 0.002(1) -0.002(1) H104A 0.026(1) 0.029(1) 0.026(1) 0.016(1) 0.001(1) 0.000(1) H104B 0.026(1) 0.029(1) 0.026(1) 0.016(1) 0.001(1) 0.000(1) H105A 0.057(2) 0.040(2) 0.049(2) 0.034(2) -0.001(2) -0.008(2) H105B 0.057(2) 0.040(2) 0.049(2) 0.034(2) -0.001(2) -0.008(2) H106 0.046(1) 0.047(2) 0.024(1) 0.031(1) 0.004(1) 0.006(1) H107 0.025(1) 0.034(1) 0.022(1) 0.016(1) 0.000(1) -0.002(1) H108A 0.031(2) 0.040(2) 0.027(2) 0.020(2) 0.008(1) 0.001(1) H108B 0.031(2) 0.040(2) 0.027(2) 0.020(2) 0.008(1) 0.001(1) H109 0.042(2) 0.040(2) 0.024(2) 0.027(2) 0.004(1) -0.002(1) H111A 0.041(1) 0.041(1) 0.025(1) 0.024(1) -0.001(1) -0.008(1) H111B 0.041(1) 0.041(1) 0.025(1) 0.024(1) -0.001(1) -0.008(1) H111C 0.041(1) 0.041(1) 0.025(1) 0.024(1) -0.001(1) -0.008(1) H118A 0.037(2) 0.055(2) 0.043(2) 0.031(2) 0.004(2) -0.001(2) H118B 0.037(2) 0.055(2) 0.043(2) 0.031(2) 0.004(2) -0.001(2) H118C 0.037(2) 0.055(2) 0.043(2) 0.031(2) 0.004(2) -0.001(2) H119A 0.053(2) 0.034(1) 0.038(1) 0.025(1) 0.002(1) 0.002(1) H119B 0.053(2) 0.034(1) 0.038(1) 0.025(1) 0.002(1) 0.002(1) H119C 0.053(2) 0.034(1) 0.038(1) 0.025(1) 0.002(1) 0.002(1) H121A 0.094(11) 0.041(8) 0.064(7) 0.033(9) 0.010(8) -0.005(7) H121B 0.089(4) 0.038(4) 0.062(4) 0.029(4) 0.004(4) -0.011(4) H121C 0.092(8) 0.040(7) 0.060(3) 0.031(7) 0.006(3) -0.009(2) H122A 0.061(3) 0.067(3) 0.025(2) 0.043(2) 0.007(2) -0.005(2) H122B 0.061(3) 0.067(3) 0.025(2) 0.043(2) 0.007(2) -0.005(2) H122C 0.061(3) 0.067(3) 0.025(2) 0.043(2) 0.007(2) -0.005(2) H202 0.048(2) 0.033(2) 0.032(2) 0.023(2) 0.006(2) 0.006(1) H203 0.042(2) 0.031(2) 0.030(2) 0.024(2) -0.006(1) 0.003(1) H204A 0.032(1) 0.032(1) 0.032(1) 0.020(1) 0.000(1) 0.004(1) H204B 0.032(1) 0.032(1) 0.032(1) 0.020(1) 0.000(1) 0.004(1) H205A 0.047(2) 0.047(2) 0.043(2) 0.029(2) -0.006(2) 0.004(2) H205B 0.047(2) 0.047(2) 0.043(2) 0.029(2) -0.006(2) 0.004(2) H206 0.059(2) 0.050(2) 0.030(1) 0.038(1) 0.010(1) 0.007(1) H207 0.042(1) 0.032(1) 0.028(1) 0.023(1) 0.000(1) 0.003(1) H208A 0.046(2) 0.034(2) 0.030(2) 0.024(2) 0.007(1) 0.010(1) H208B 0.046(2) 0.034(2) 0.030(2) 0.024(2) 0.007(1) 0.010(1) H209 0.048(2) 0.046(2) 0.029(2) 0.033(2) 0.003(1) 0.006(1) H211A 0.045(1) 0.042(1) 0.026(1) 0.028(1) -0.004(1) 0.001(1) H211B 0.045(1) 0.042(1) 0.026(1) 0.028(1) -0.004(1) 0.001(1) H211C 0.045(1) 0.042(1) 0.026(1) 0.028(1) -0.004(1) 0.001(1) H218A 0.075(3) 0.044(2) 0.038(2) 0.042(2) -0.001(2) 0.008(2) H218B 0.075(3) 0.044(2) 0.038(2) 0.042(2) -0.001(2) 0.008(2) H218C 0.075(3) 0.044(2) 0.038(2) 0.042(2) -0.001(2) 0.008(2) H219A 0.040(1) 0.060(2) 0.040(1) 0.031(1) -0.001(1) 0.002(1) H219B 0.040(1) 0.060(2) 0.040(1) 0.031(1) -0.001(1) 0.002(1) H219C 0.040(1) 0.060(2) 0.040(1) 0.031(1) -0.001(1) 0.002(1) H221A 0.049(9) 0.080(10) 0.072(7) 0.036(9) -0.001(8) 0.006(8) H221B 0.046(5) 0.076(4) 0.070(4) 0.032(4) -0.007(4) 0.000(4) H221C 0.047(7) 0.077(6) 0.068(3) 0.034(6) -0.004(2) 0.002(3) H222A 0.070(3) 0.059(3) 0.036(2) 0.044(2) -0.006(2) 0.004(2) H222B 0.070(3) 0.059(3) 0.036(2) 0.044(2) -0.006(2) 0.004(2) H222C 0.070(3) 0.059(3) 0.036(2) 0.044(2) -0.006(2) 0.004(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.516(5) . . yes C1 O10 1.344(4) . . yes C1 O12 1.205(4) . . yes C2 C3 1.524(5) . . yes C2 O13 1.434(4) . . yes C2 H2 0.999(53) . . no C3 C4 1.524(5) . . yes C3 O16 1.447(4) . . yes C3 H3 1.148(51) . . no C4 C5 1.542(5) . . yes C4 H4A 0.934(47) . . no C4 H4B 1.002(48) . . no C5 C6 1.503(5) . . yes C5 H5A 1.024(57) . . no C5 H5B 1.145(52) . . no C6 C7 1.313(6) . . yes C6 H6 0.979(54) . . no C7 C8 1.509(5) . . yes C7 H7 1.027(47) . . no C8 C9 1.518(5) . . yes C8 H8A 1.043(49) . . no C8 H8B 0.993(46) . . no C9 O10 1.470(4) . . yes C9 C11 1.513(3) . . yes C9 H9 0.966(51) . . no C11 H11A 0.978(8) . . no C11 H11B 0.978(8) . . no C11 H11C 0.978(8) . . no O13 C14 1.430(4) . . yes C14 C15 1.555(5) . . yes C14 O17 1.420(4) . . yes C14 C19 1.518(2) . . yes C15 O16 1.417(4) . . yes C15 O20 1.416(4) . . yes C15 C22 1.517(2) . . yes O17 C18 1.429(2) . . yes C18 H18A 0.982(11) . . no C18 H18B 0.982(11) . . no C18 H18C 0.982(11) . . no C19 H19A 0.978(8) . . no C19 H19B 0.978(8) . . no C19 H19C 0.978(8) . . no O20 C21 1.424(2) . . yes C21 H21A 0.982(11) . . no C21 H21B 0.982(11) . . no C21 H21C 0.982(11) . . no C22 H22A 0.978(8) . . no C22 H22B 0.978(8) . . no C22 H22C 0.978(8) . . no C101 C102 1.523(4) . . yes C101 O110 1.325(4) . . yes C101 O112 1.201(4) . . yes C102 C103 1.530(4) . . yes C102 O113 1.422(4) . . yes C102 H102 0.927(53) . . no C103 C104 1.531(5) . . yes C103 O116 1.427(4) . . yes C103 H103 0.969(47) . . no C104 C105 1.551(5) . . yes C104 H104A 1.008(48) . . no C104 H104B 1.051(47) . . no C105 C106 1.504(6) . . yes C105 H105A 1.014(58) . . no C105 H105B 0.815(57) . . no C106 C107 1.335(6) . . yes C106 H106 0.992(50) . . no C107 C108 1.505(5) . . yes C107 H107 1.091(45) . . no C108 C109 1.521(5) . . yes C108 H108A 1.024(50) . . no C108 H108B 0.956(46) . . no C109 O110 1.472(4) . . yes C109 C111 1.513(3) . . yes C109 H109 1.044(49) . . no C111 H111A 0.978(8) . . no C111 H111B 0.978(8) . . no C111 H111C 0.978(8) . . no O113 C114 1.430(4) . . yes C114 C115 1.559(5) . . yes C114 O117 1.408(4) . . yes C114 C119 1.518(2) . . yes C115 O116 1.417(4) . . yes C115 O120 1.414(4) . . yes C115 C122 1.517(2) . . yes O117 C118 1.429(2) . . yes C118 H118A 0.982(11) . . no C118 H118B 0.982(11) . . no C118 H118C 0.982(11) . . no C119 H119A 0.978(8) . . no C119 H119B 0.978(8) . . no C119 H119C 0.978(8) . . no O120 C121 1.424(2) . . yes C121 H121A 0.982(11) . . no C121 H121B 0.982(11) . . no C121 H121C 0.982(11) . . no C122 H122A 0.978(8) . . no C122 H122B 0.978(8) . . no C122 H122C 0.978(8) . . no C201 C202 1.513(4) . . yes C201 O210 1.350(4) . . yes C201 O212 1.200(4) . . yes C202 C203 1.531(5) . . yes C202 O213 1.427(4) . . yes C202 H202 0.960(51) . . no C203 C204 1.513(5) . . yes C203 O216 1.441(4) . . yes C203 H203 0.987(49) . . no C204 C205 1.537(5) . . yes C204 H204A 0.962(48) . . no C204 H204B 1.013(48) . . no C205 C206 1.509(5) . . yes C205 H205A 1.081(54) . . no C205 H205B 1.010(53) . . no C206 C207 1.323(5) . . yes C206 H206 1.016(50) . . no C207 C208 1.497(5) . . yes C207 H207 1.162(46) . . no C208 C209 1.526(5) . . yes C208 H208A 1.072(51) . . no C208 H208B 1.017(46) . . no C209 O210 1.474(4) . . yes C209 C211 1.513(3) . . yes C209 H209 1.032(51) . . no C211 H211A 0.978(8) . . no C211 H211B 0.978(8) . . no C211 H211C 0.978(8) . . no O213 C214 1.433(4) . . yes C214 C215 1.549(5) . . yes C214 O217 1.423(4) . . yes C214 C219 1.518(2) . . yes C215 O216 1.419(4) . . yes C215 O220 1.411(4) . . yes C215 C222 1.517(2) . . yes O217 C218 1.429(2) . . yes C218 H218A 0.982(11) . . no C218 H218B 0.982(11) . . no C218 H218C 0.982(11) . . no C219 H219A 0.978(8) . . no C219 H219B 0.978(8) . . no C219 H219C 0.978(8) . . no O220 C221 1.424(2) . . yes C221 H221A 0.982(11) . . no C221 H221B 0.982(11) . . no C221 H221C 0.982(11) . . no C222 H222A 0.978(8) . . no C222 H222B 0.978(8) . . no C222 H222C 0.978(8) . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 O10 109.4(3) . . . yes C2 C1 O12 126.1(3) . . . yes O10 C1 O12 124.5(3) . . . yes C1 C2 C3 111.4(3) . . . yes C1 C2 O13 106.4(2) . . . yes C1 C2 H2 109.6(28) . . . no C3 C2 O13 110.7(3) . . . yes C3 C2 H2 115.0(29) . . . no O13 C2 H2 102.9(27) . . . no C2 C3 C4 113.7(3) . . . yes C2 C3 O16 106.3(3) . . . yes C2 C3 H3 109.4(23) . . . no C4 C3 O16 106.3(3) . . . yes C4 C3 H3 115.0(24) . . . yes O16 C3 H3 105.4(23) . . . yes C3 C4 C5 114.1(3) . . . yes C3 C4 H4A 111.4(28) . . . no C3 C4 H4B 104.1(27) . . . no C5 C4 H4A 113.5(29) . . . no C5 C4 H4B 116.4(26) . . . no H4A C4 H4B 95.7(39) . . . no C4 C5 C6 113.1(3) . . . yes C4 C5 H5A 111.4(30) . . . no C4 C5 H5B 105.0(26) . . . no C6 C5 H5A 104.4(29) . . . no C6 C5 H5B 114.9(26) . . . no H5A C5 H5B 108.1(41) . . . no C5 C6 C7 126.4(4) . . . yes C5 C6 H6 105.7(30) . . . no C7 C6 H6 127.9(31) . . . no C6 C7 C8 125.7(4) . . . yes C6 C7 H7 110.3(26) . . . no C8 C7 H7 123.7(26) . . . no C7 C8 C9 114.1(3) . . . yes C7 C8 H8A 112.4(26) . . . no C7 C8 H8B 118.3(26) . . . no C9 C8 H8A 106.2(25) . . . no C9 C8 H8B 104.5(27) . . . no H8A C8 H8B 99.7(37) . . . no C8 C9 O10 109.6(3) . . . yes C8 C9 C11 113.9(3) . . . yes C8 C9 H9 108.8(29) . . . no O10 C9 C11 104.9(2) . . . yes O10 C9 H9 107.9(28) . . . no C11 C9 H9 111.5(29) . . . no C1 O10 C9 117.2(2) . . . yes C9 C11 H11A 110.1(5) . . . no C9 C11 H11B 110.1(5) . . . no C9 C11 H11C 110.1(5) . . . no H11A C11 H11B 108.8(5) . . . no H11A C11 H11C 108.8(5) . . . no H11B C11 H11C 108.8(5) . . . no C2 O13 C14 112.4(2) . . . yes O13 C14 C15 110.2(2) . . . yes O13 C14 O17 109.8(2) . . . yes O13 C14 C19 105.1(2) . . . yes C15 C14 O17 105.1(2) . . . yes C15 C14 C19 114.0(3) . . . yes O17 C14 C19 112.7(3) . . . yes C14 C15 O16 110.3(3) . . . yes C14 C15 O20 104.1(2) . . . yes C14 C15 C22 112.8(3) . . . yes O16 C15 O20 111.5(3) . . . yes O16 C15 C22 105.1(3) . . . yes O20 C15 C22 113.1(3) . . . yes C3 O16 C15 114.8(2) . . . yes C14 O17 C18 116.8(2) . . . yes O17 C18 H18A 108.7(7) . . . no O17 C18 H18B 108.7(7) . . . no O17 C18 H18C 108.7(7) . . . no H18A C18 H18B 110.3(7) . . . no H18A C18 H18C 110.3(7) . . . no H18B C18 H18C 110.3(7) . . . no C14 C19 H19A 110.1(5) . . . no C14 C19 H19B 110.1(5) . . . no C14 C19 H19C 110.1(5) . . . no H19A C19 H19B 108.8(5) . . . no H19A C19 H19C 108.8(5) . . . no H19B C19 H19C 108.8(5) . . . no C15 O20 C21 115.9(3) . . . yes O20 C21 H21A 108.7(7) . . . no O20 C21 H21B 108.7(7) . . . no O20 C21 H21C 108.7(7) . . . no H21A C21 H21B 110.3(7) . . . no H21A C21 H21C 110.3(7) . . . no H21B C21 H21C 110.3(7) . . . no C15 C22 H22A 110.1(5) . . . no C15 C22 H22B 110.1(5) . . . no C15 C22 H22C 110.1(5) . . . no H22A C22 H22B 108.8(5) . . . no H22A C22 H22C 108.8(5) . . . no H22B C22 H22C 108.8(5) . . . no C102 C101 O110 110.1(3) . . . yes C102 C101 O112 123.9(3) . . . yes O110 C101 O112 125.9(3) . . . yes C101 C102 C103 112.1(2) . . . yes C101 C102 O113 107.7(2) . . . yes C101 C102 H102 105.7(29) . . . no C103 C102 O113 110.5(3) . . . yes C103 C102 H102 108.6(30) . . . no O113 C102 H102 112.1(31) . . . no C102 C103 C104 113.1(3) . . . yes C102 C103 O116 107.6(2) . . . yes C102 C103 H103 106.7(28) . . . no C104 C103 O116 106.7(3) . . . yes C104 C103 H103 112.3(29) . . . no O116 C103 H103 110.3(28) . . . no C103 C104 C105 113.2(3) . . . yes C103 C104 H104A 108.2(23) . . . no C103 C104 H104B 113.4(24) . . . no C105 C104 H104A 103.9(25) . . . no C105 C104 H104B 104.4(23) . . . no H104A C104 H104B 113.5(34) . . . no C104 C105 C106 112.8(3) . . . yes C104 C105 H105A 110.6(31) . . . no C104 C105 H105B 106.0(37) . . . no C106 C105 H105A 111.8(28) . . . no C106 C105 H105B 111.1(36) . . . no H105A C105 H105B 104.0(48) . . . no C105 C106 C107 126.3(3) . . . yes C105 C106 H106 114.5(28) . . . no C107 C106 H106 119.2(28) . . . no C106 C107 C108 124.6(3) . . . yes C106 C107 H107 127.4(23) . . . no C108 C107 H107 108.0(22) . . . no C107 C108 C109 113.2(3) . . . yes C107 C108 H108A 108.7(26) . . . no C107 C108 H108B 106.9(27) . . . no C109 C108 H108A 108.9(26) . . . no C109 C108 H108B 110.2(28) . . . no H108A C108 H108B 108.9(37) . . . no C108 C109 O110 108.7(3) . . . yes C108 C109 C111 114.4(3) . . . yes C108 C109 H109 112.3(27) . . . no O110 C109 C111 106.2(2) . . . yes O110 C109 H109 103.3(26) . . . no C111 C109 H109 111.0(26) . . . no C101 O110 C109 117.8(2) . . . yes C109 C111 H111A 110.1(5) . . . no C109 C111 H111B 110.1(5) . . . no C109 C111 H111C 110.1(5) . . . no H111A C111 H111B 108.8(5) . . . no H111A C111 H111C 108.8(5) . . . no H111B C111 H111C 108.8(5) . . . no C102 O113 C114 113.2(2) . . . yes O113 C114 C115 109.7(2) . . . yes O113 C114 O117 110.9(2) . . . yes O113 C114 C119 105.8(2) . . . yes C115 C114 O117 103.8(2) . . . yes C115 C114 C119 112.8(3) . . . yes O117 C114 C119 113.9(3) . . . yes C114 C115 O116 109.7(2) . . . yes C114 C115 O120 103.9(2) . . . yes C114 C115 C122 113.4(3) . . . yes O116 C115 O120 111.0(3) . . . yes O116 C115 C122 105.3(2) . . . yes O120 C115 C122 113.7(3) . . . yes C103 O116 C115 114.8(2) . . . yes C114 O117 C118 115.0(2) . . . yes O117 C118 H118A 108.7(7) . . . no O117 C118 H118B 108.7(7) . . . no O117 C118 H118C 108.7(7) . . . no H118A C118 H118B 110.3(7) . . . no H118A C118 H118C 110.3(7) . . . no H118B C118 H118C 110.3(7) . . . no C114 C119 H119A 110.1(5) . . . no C114 C119 H119B 110.1(5) . . . no C114 C119 H119C 110.1(5) . . . no H119A C119 H119B 108.8(5) . . . no H119A C119 H119C 108.8(5) . . . no H119B C119 H119C 108.8(5) . . . no C115 O120 C121 116.5(3) . . . yes O120 C121 H121A 108.7(7) . . . no O120 C121 H121B 108.7(7) . . . no O120 C121 H121C 108.7(7) . . . no H121A C121 H121B 110.3(7) . . . no H121A C121 H121C 110.3(7) . . . no H121B C121 H121C 110.3(7) . . . no C115 C122 H122A 110.1(5) . . . no C115 C122 H122B 110.1(5) . . . no C115 C122 H122C 110.1(5) . . . no H122A C122 H122B 108.8(5) . . . no H122A C122 H122C 108.8(5) . . . no H122B C122 H122C 108.8(5) . . . no C202 C201 O210 110.0(3) . . . yes C202 C201 O212 126.2(3) . . . yes O210 C201 O212 123.7(3) . . . yes C201 C202 C203 111.2(3) . . . yes C201 C202 O213 106.5(2) . . . yes C201 C202 H202 112.7(30) . . . no C203 C202 O213 110.5(3) . . . yes C203 C202 H202 111.4(30) . . . no O213 C202 H202 104.1(29) . . . no C202 C203 C204 113.6(3) . . . yes C202 C203 O216 106.7(3) . . . yes C202 C203 H203 106.6(28) . . . no C204 C203 O216 106.8(3) . . . yes C204 C203 H203 114.6(27) . . . no O216 C203 H203 108.3(27) . . . no C203 C204 C205 113.4(3) . . . yes C203 C204 H204A 109.9(27) . . . no C203 C204 H204B 109.3(26) . . . no C205 C204 H204A 115.1(27) . . . no C205 C204 H204B 106.3(25) . . . no H204A C204 H204B 102.1(38) . . . no C204 C205 C206 112.8(3) . . . yes C204 C205 H205A 111.1(29) . . . no C204 C205 H205B 108.9(29) . . . no C206 C205 H205A 104.5(27) . . . no C206 C205 H205B 115.4(29) . . . no H205A C205 H205B 103.7(42) . . . no C205 C206 C207 126.5(3) . . . yes C205 C206 H206 115.7(28) . . . no C207 C206 H206 117.5(28) . . . no C206 C207 C208 125.0(3) . . . yes C206 C207 H207 115.8(21) . . . no C208 C207 H207 118.6(22) . . . no C207 C208 C209 113.6(3) . . . yes C207 C208 H208A 113.1(26) . . . no C207 C208 H208B 116.5(27) . . . no C209 C208 H208A 105.7(25) . . . no C209 C208 H208B 99.9(27) . . . no H208A C208 H208B 106.6(36) . . . no C208 C209 O210 109.9(3) . . . yes C208 C209 C211 112.9(3) . . . yes C208 C209 H209 112.2(28) . . . no O210 C209 C211 105.5(2) . . . yes O210 C209 H209 104.5(26) . . . no C211 C209 H209 111.3(28) . . . no C201 O210 C209 116.6(2) . . . yes C209 C211 H211A 110.1(5) . . . no C209 C211 H211B 110.1(5) . . . no C209 C211 H211C 110.1(5) . . . no H211A C211 H211B 108.8(5) . . . no H211A C211 H211C 108.8(5) . . . no H211B C211 H211C 108.8(5) . . . no C202 O213 C214 112.0(2) . . . yes O213 C214 C215 109.3(2) . . . yes O213 C214 O217 110.1(3) . . . yes O213 C214 C219 105.3(2) . . . yes C215 C214 O217 104.9(2) . . . yes C215 C214 C219 114.2(3) . . . yes O217 C214 C219 113.1(3) . . . yes C214 C215 O216 110.4(2) . . . yes C214 C215 O220 104.8(2) . . . yes C214 C215 C222 112.7(3) . . . yes O216 C215 O220 111.2(3) . . . yes O216 C215 C222 105.0(3) . . . yes O220 C215 C222 112.9(3) . . . yes C203 O216 C215 114.4(2) . . . yes C214 O217 C218 116.4(3) . . . yes O217 C218 H218A 108.7(7) . . . no O217 C218 H218B 108.7(7) . . . no O217 C218 H218C 108.7(7) . . . no H218A C218 H218B 110.3(7) . . . no H218A C218 H218C 110.3(7) . . . no H218B C218 H218C 110.3(7) . . . no C214 C219 H219A 110.1(5) . . . no C214 C219 H219B 110.1(5) . . . no C214 C219 H219C 110.1(5) . . . no H219A C219 H219B 108.8(5) . . . no H219A C219 H219C 108.8(5) . . . no H219B C219 H219C 108.8(5) . . . no C215 O220 C221 116.2(3) . . . yes O220 C221 H221A 108.7(7) . . . no O220 C221 H221B 108.7(7) . . . no O220 C221 H221C 108.7(7) . . . no H221A C221 H221B 110.3(7) . . . no H221A C221 H221C 110.3(7) . . . no H221B C221 H221C 110.3(7) . . . no C215 C222 H222A 110.1(5) . . . no C215 C222 H222B 110.1(5) . . . no C215 C222 H222C 110.1(5) . . . no H222A C222 H222B 108.8(5) . . . no H222A C222 H222C 108.8(5) . . . no H222B C222 H222C 108.8(5) . . . no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C2 C1 O10 100.5(3) . . . . no O13 C2 C1 O10 -138.7(3) . . . . no C3 C2 C1 O12 -78.1(4) . . . . no O13 C2 C1 O12 42.7(4) . . . . no C9 O10 C1 C2 -172.7(3) . . . . no C9 O10 C1 O12 5.9(5) . . . . no C4 C3 C2 C1 -66.0(4) . . . . no O16 C3 C2 C1 177.4(3) . . . . no C4 C3 C2 O13 175.8(3) . . . . no O16 C3 C2 O13 59.2(3) . . . . no C14 O13 C2 C1 178.4(3) . . . . no C14 O13 C2 C3 -60.3(3) . . . . no C5 C4 C3 C2 85.2(4) . . . . no C5 C4 C3 O16 -158.2(3) . . . . no C15 O16 C3 C2 -59.0(3) . . . . no C15 O16 C3 C4 179.5(3) . . . . no C6 C5 C4 C3 -135.4(3) . . . . no C7 C6 C5 C4 114.9(4) . . . . no C8 C7 C6 C5 -0.2(7) . . . . no C9 C8 C7 C6 -91.6(5) . . . . no O10 C9 C8 C7 55.5(4) . . . . no C11 C9 C8 C7 -61.6(4) . . . . no C1 O10 C9 C8 80.4(3) . . . . no C1 O10 C9 C11 -157.0(3) . . . . no C15 C14 O13 C2 54.3(3) . . . . no O17 C14 O13 C2 -61.0(3) . . . . no C19 C14 O13 C2 177.5(3) . . . . no O16 C15 C14 O13 -50.6(3) . . . . no O20 C15 C14 O13 69.2(3) . . . . no C22 C15 C14 O13 -167.8(3) . . . . no O16 C15 C14 O17 67.6(3) . . . . no O20 C15 C14 O17 -172.6(2) . . . . no C22 C15 C14 O17 -49.5(3) . . . . no O16 C15 C14 C19 -168.5(2) . . . . no O20 C15 C14 C19 -48.7(3) . . . . no C22 C15 C14 C19 74.4(3) . . . . no C18 O17 C14 O13 -69.2(3) . . . . no C18 O17 C14 C15 172.3(2) . . . . no C18 O17 C14 C19 47.6(4) . . . . no C3 O16 C15 C14 55.6(3) . . . . no C3 O16 C15 O20 -59.5(3) . . . . no C3 O16 C15 C22 177.5(3) . . . . no C21 O20 C15 C14 -175.2(3) . . . . no C21 O20 C15 O16 -56.2(3) . . . . no C21 O20 C15 C22 62.0(4) . . . . no C103 C102 C101 O110 98.2(3) . . . . no O113 C102 C101 O110 -140.0(3) . . . . no C103 C102 C101 O112 -80.3(4) . . . . no O113 C102 C101 O112 41.5(4) . . . . no C109 O110 C101 C102 -173.5(2) . . . . no C109 O110 C101 O112 4.9(5) . . . . no C104 C103 C102 C101 -64.9(4) . . . . no O116 C103 C102 C101 177.5(2) . . . . no C104 C103 C102 O113 175.0(3) . . . . no O116 C103 C102 O113 57.3(3) . . . . no C114 O113 C102 C101 178.4(2) . . . . no C114 O113 C102 C103 -58.8(3) . . . . no C105 C104 C103 C102 86.0(4) . . . . no C105 C104 C103 O116 -155.8(3) . . . . no C115 O116 C103 C102 -58.5(3) . . . . no C115 O116 C103 C104 179.8(3) . . . . no C106 C105 C104 C103 -137.2(3) . . . . no C107 C106 C105 C104 114.2(4) . . . . no C108 C107 C106 C105 0.5(6) . . . . no C109 C108 C107 C106 -92.8(5) . . . . no O110 C109 C108 C107 58.3(4) . . . . no C111 C109 C108 C107 -60.3(4) . . . . no C101 O110 C109 C108 80.4(3) . . . . no C101 O110 C109 C111 -156.0(3) . . . . no C115 C114 O113 C102 55.0(3) . . . . no O117 C114 O113 C102 -59.2(3) . . . . no C119 C114 O113 C102 176.9(3) . . . . no O116 C115 C114 O113 -51.6(3) . . . . no O120 C115 C114 O113 67.1(3) . . . . no C122 C115 C114 O113 -168.9(2) . . . . no O116 C115 C114 O117 67.0(3) . . . . no O120 C115 C114 O117 -174.2(2) . . . . no C122 C115 C114 O117 -50.3(3) . . . . no O116 C115 C114 C119 -169.3(2) . . . . no O120 C115 C114 C119 -50.5(3) . . . . no C122 C115 C114 C119 73.4(3) . . . . no C118 O117 C114 O113 -63.0(3) . . . . no C118 O117 C114 C115 179.2(3) . . . . no C118 O117 C114 C119 56.2(4) . . . . no C103 O116 C115 C114 56.3(3) . . . . no C103 O116 C115 O120 -58.1(3) . . . . no C103 O116 C115 C122 178.6(3) . . . . no C121 O120 C115 C114 -176.4(3) . . . . no C121 O120 C115 O116 -58.5(3) . . . . no C121 O120 C115 C122 59.9(4) . . . . no C203 C202 C201 O210 99.0(3) . . . . no O213 C202 C201 O210 -140.5(3) . . . . no C203 C202 C201 O212 -78.6(4) . . . . no O213 C202 C201 O212 41.9(4) . . . . no C209 O210 C201 C202 -171.4(3) . . . . no C209 O210 C201 O212 6.3(5) . . . . no C204 C203 C202 C201 -65.8(4) . . . . no O216 C203 C202 C201 176.8(2) . . . . no C204 C203 C202 O213 176.0(3) . . . . no O216 C203 C202 O213 58.7(3) . . . . no C214 O213 C202 C201 177.9(3) . . . . no C214 O213 C202 C203 -61.1(3) . . . . no C205 C204 C203 C202 88.6(4) . . . . no C205 C204 C203 O216 -154.1(3) . . . . no C215 O216 C203 C202 -58.1(3) . . . . no C215 O216 C203 C204 -179.9(3) . . . . no C206 C205 C204 C203 -136.9(3) . . . . no C207 C206 C205 C204 112.3(4) . . . . no C208 C207 C206 C205 0.9(6) . . . . no C209 C208 C207 C206 -93.3(4) . . . . no O210 C209 C208 C207 57.3(4) . . . . no C211 C209 C208 C207 -60.1(4) . . . . no C201 O210 C209 C208 79.0(3) . . . . no C201 O210 C209 C211 -159.0(3) . . . . no C215 C214 O213 C202 56.4(3) . . . . no O217 C214 O213 C202 -58.3(3) . . . . no C219 C214 O213 C202 179.5(3) . . . . no O216 C215 C214 O213 -52.6(3) . . . . no O220 C215 C214 O213 67.2(3) . . . . no C222 C215 C214 O213 -169.7(3) . . . . no O216 C215 C214 O217 65.4(3) . . . . no O220 C215 C214 O217 -174.8(2) . . . . no C222 C215 C214 O217 -51.6(3) . . . . no O216 C215 C214 C219 -170.2(2) . . . . no O220 C215 C214 C219 -50.4(3) . . . . no C222 C215 C214 C219 72.7(4) . . . . no C218 O217 C214 O213 -61.4(3) . . . . no C218 O217 C214 C215 -178.9(3) . . . . no C218 O217 C214 C219 56.0(4) . . . . no C203 O216 C215 C214 56.3(3) . . . . no C203 O216 C215 O220 -59.6(3) . . . . no C203 O216 C215 C222 178.0(3) . . . . no C221 O220 C215 C214 -176.2(3) . . . . no C221 O220 C215 O216 -57.0(3) . . . . no C221 O220 C215 C222 60.7(4) . . . . no #===END