# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 188/171 data_CRYSTALS_cif _audit_creation_date 99-03-11 _audit_creation_method CRYSTALS # LOM12BIS #**************************************************************************** # The contents of this file between this point and the next #***** line # are held in the file CRYSTALS\SCRIPT\CIF.REF. # This is a character file which you may edit to reflect local # conditions # # 1. SUBMISSION DETAILS _publ_contact_author ; John S. Lomas # Name and address of author for correspondence ; _publ_contact_author_phone '00 33 4427 6838' _publ_contact_author_fax ' 00 33 4427 6814' _publ_contact_author_email ' lomas@itodys.jussieu.fr ' _publ_requested_journal ' J. Chem. Soc., Perkin Trans. 2 ' _publ_requested_coeditor_name ' ? ' _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica C. The figures have been sent by mail, and structure factor listings can be made available if requested. ; #============================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; Competing intermolecular and intramolecular hydride transfers in the ionic hydrogenation of (2-alkoxyphenyl)di(1-adamantyl)methanols ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. #============================================================================== # 4. TEXT _publ_section_abstract ; ? #Text of the abstract ; _publ_section_comment ; ? #Text of the paper ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; _publ_section_references ; # Add your own references - in alphabetic order Carruthers, J.R. and Watkin, D.J. (1979), (Chebychev Weighting) Acta Cryst, A35, 698-699 Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of Gottingen, Federal Republic of Germany. Watkin, D.J., Prout, C.K. Carruthers, R.J. & Betteridge, P. (1996) CRYSTALS Issue 10. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. (1994), RC93, Chemical Crystallography Laboratory, Oxford, UK. ; _publ_section_figure_captions ; ? #Captions to figures ; _publ_section_acknowledgements ; ? ; #========================================================================== # Now, all the strucure specific goodies #========================================================================== _computing_data_collection 'CAD-4 software (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD-4 software (Enraf-Nonius, 1989)' _computing_data_reduction ; RC93 (Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. 1994) ; _computing_structure_refinement ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_publication_material ; CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996) ; _computing_molecular_graphics ; CAMERON (Watkin, Prout & Pearce, 1996) ; # _computing_structure_solution 'SHELXS86 (Sheldrick, 1986)' #========================================================================== # NOW THE GOODIES TO BE ENTERED BY HAND #========================================================================== _chemical_melting_point 148C _diffrn_radiation_monochromator ' graphite ' _diffrn_measurement_device ' Enraf-nonius CAD4 ' _refine_ls_matrix_type ' full ' _refine_ls_weighting_scheme ; Chebychev polynomial (Carruthers & Watkin, 1979) ; _atom_sites_solution_primary ' Direct_Methods ' _atom_sites_solution_hydrogens ' Difference Fourier map ' _refine_ls_hydrogen_treatment ; one overall isotropic thermal parameter refined ; #**************************************************************************** _chemical_name_systematic ; anti-(2-anisyl)di(1-adamantyl)methane ; _cell_length_a 10.945(8) _cell_angle_alpha 90 _cell_length_b 25.070(11) _cell_angle_beta 104.71(5) _cell_length_c 16.530(10) _cell_angle_gamma 90 _cell_volume 4387.03 _symmetry_cell_setting 'Monoclinic ' _symmetry_space_group_name_H-M 'P 1 21/n 1 ' 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' 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 ' 0.0020 0.0020 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 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'O ' 0.0080 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' _chemical_formula_sum ' C28 H38 O1 ' _chemical_formula_moiety ' C28 H38 O1 ' _chemical_compound_source ; synthesis in laboratory ; _chemical_formula_weight 390.6 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11.8 _cell_measurement_theta_max 12.2 _cell_measurement_temperature 295K _cell_formula_units_Z 8 _exptl_crystal_description ' prism ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.32 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.18 _exptl_crystal_density_meas ? _exptl_crystal_F_000 1712.31 _exptl_absorpt_coefficient_mu 0.06 _exptl_absorpt_correction_type ' none ' _diffrn_standards_interval_time 3600s _diffrn_standards_number 2 _diffrn_standards_decay_% 7.20 _diffrn_ambient_temperature 295K _diffrn_reflns_number 8342 _reflns_number_total 7699 _diffrn_reflns_av_R_equivalents 0.01 _reflns_number_observed 3523 _diffrn_reflns_theta_min 1 _diffrn_reflns_theta_max 25 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -13 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 29 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _reflns_observed_criterion >3.00\s(I) _refine_diff_density_min -0.18 _refine_diff_density_max 0.19 _refine_ls_number_reflns 3523 _refine_ls_number_parameters 524 _refine_ls_R_factor_obs 0.0527 _refine_ls_wR_factor_obs 0.0665 _refine_ls_goodness_of_fit_obs 0.8625 _refine_ls_shift/esd_max 1.627206 _refine_ls_structure_factor_coef F _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_measurement_method 2\q/\w loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type O1 0.7446(3) 0.1263(1) 0.5261(2) 0.0659 1.0000 Uani O11 0.7329(2) 0.0314(1) 1.0088(2) 0.0555 1.0000 Uani C1 0.8877(4) 0.1988(2) 0.5542(2) 0.0494 1.0000 Uani C2 0.7810(4) 0.1740(2) 0.5668(2) 0.0543 1.0000 Uani C3 0.7116(4) 0.1962(2) 0.6187(2) 0.0618 1.0000 Uani C4 0.7491(6) 0.2441(3) 0.6556(3) 0.0705 1.0000 Uani C5 0.8523(6) 0.2712(2) 0.6429(3) 0.0745 1.0000 Uani C6 0.9188(4) 0.2477(2) 0.5922(2) 0.0597 1.0000 Uani C7 0.6173(4) 0.1101(2) 0.5096(3) 0.0779 1.0000 Uani C10 0.9720(3) 0.1778(1) 0.5001(2) 0.0462 1.0000 Uani C11 0.6150(3) 0.0941(1) 0.9147(2) 0.0410 1.0000 Uani C12 0.6318(3) 0.0656(1) 0.9891(2) 0.0449 1.0000 Uani C13 0.5505(4) 0.0714(2) 1.0404(3) 0.0587 1.0000 Uani C14 0.4467(5) 0.1048(2) 1.0151(3) 0.0675 1.0000 Uani C15 0.4239(4) 0.1313(2) 0.9410(3) 0.0662 1.0000 Uani C16 0.5078(3) 0.1259(2) 0.8916(2) 0.0509 1.0000 Uani C17 0.7599(4) 0.0040(2) 1.0863(3) 0.0694 1.0000 Uani C20 0.7077(3) 0.0962(1) 0.8583(2) 0.0385 1.0000 Uani C101 1.0674(3) 0.1336(1) 0.5486(2) 0.0419 1.0000 Uani C102 1.1707(3) 0.1221(2) 0.5028(3) 0.0569 1.0000 Uani C103 1.2732(4) 0.0845(2) 0.5541(3) 0.0633 1.0000 Uani C104 1.3347(4) 0.1111(2) 0.6370(4) 0.0755 1.0000 Uani C105 1.2356(4) 0.1207(2) 0.6853(3) 0.0649 1.0000 Uani C106 1.1745(4) 0.0689(2) 0.6997(3) 0.0673 1.0000 Uani C107 1.1121(4) 0.0432(2) 0.6164(3) 0.0574 1.0000 Uani C108 1.0093(4) 0.0812(1) 0.5662(2) 0.0524 1.0000 Uani C109 1.1339(4) 0.1583(2) 0.6339(3) 0.0614 1.0000 Uani C110 1.2118(4) 0.0331(2) 0.5690(3) 0.0600 1.0000 Uani C201 0.9036(3) 0.1718(1) 0.4037(2) 0.0412 1.0000 Uani C202 0.9940(4) 0.1909(2) 0.3511(3) 0.0678 1.0000 Uani C203 0.9292(4) 0.1903(2) 0.2570(3) 0.0678 1.0000 Uani C204 0.8814(5) 0.1345(2) 0.2296(3) 0.0679 1.0000 Uani C205 0.7910(5) 0.1168(2) 0.2787(3) 0.0663 1.0000 Uani C206 0.6794(4) 0.1539(2) 0.2618(3) 0.0712 1.0000 Uani C207 0.7249(4) 0.2098(2) 0.2874(2) 0.0576 1.0000 Uani C208 0.7890(4) 0.2094(2) 0.3817(2) 0.0551 1.0000 Uani C209 0.8591(4) 0.1159(1) 0.3721(2) 0.0522 1.0000 Uani C210 0.8160(5) 0.2285(2) 0.2396(3) 0.0718 1.0000 Uani C301 0.8211(3) 0.1354(1) 0.8967(2) 0.0382 1.0000 Uani C302 0.9104(3) 0.1434(2) 0.8392(2) 0.0495 1.0000 Uani C303 1.0120(4) 0.1848(2) 0.8745(3) 0.0567 1.0000 Uani C304 0.9510(4) 0.2389(2) 0.8807(3) 0.0616 1.0000 Uani C305 0.8631(4) 0.2330(2) 0.9373(2) 0.0569 1.0000 Uani C306 0.9368(4) 0.2165(2) 1.0233(2) 0.0598 1.0000 Uani C307 1.0009(4) 0.1634(2) 1.0183(2) 0.0578 1.0000 Uani C308 0.9002(3) 0.1208(1) 0.9840(2) 0.0480 1.0000 Uani C309 0.7619(4) 0.1911(1) 0.9037(2) 0.0520 1.0000 Uani C310 1.0885(4) 0.1684(2) 0.9611(3) 0.0639 1.0000 Uani C401 0.7301(3) 0.0409(1) 0.8182(2) 0.0385 1.0000 Uani C402 0.7329(4) 0.0521(2) 0.7264(2) 0.0527 1.0000 Uani C403 0.7441(4) 0.0006(2) 0.6786(2) 0.0564 1.0000 Uani C404 0.8625(4) -0.0284(2) 0.7221(3) 0.0627 1.0000 Uani C405 0.8591(4) -0.0417(2) 0.8121(2) 0.0570 1.0000 Uani C406 0.7454(5) -0.0774(2) 0.8088(3) 0.0651 1.0000 Uani C407 0.6254(4) -0.0477(2) 0.7661(3) 0.0635 1.0000 Uani C408 0.6146(3) 0.0047(2) 0.8123(2) 0.0519 1.0000 Uani C409 0.8491(3) 0.0098(1) 0.8597(2) 0.0462 1.0000 Uani C410 0.6285(5) -0.0340(2) 0.6768(3) 0.0718 1.0000 Uani H10 1.0434 0.2104 0.5015 0.083(2) 1.0000 Uiso H20 0.6565 0.1195 0.8091 0.083(2) 1.0000 Uiso H31 0.6287 0.1714 0.6198 0.083(2) 1.0000 Uiso H41 0.6979 0.2607 0.6902 0.083(2) 1.0000 Uiso H51 0.8983 0.3064 0.6669 0.083(2) 1.0000 Uiso H61 0.9993 0.2699 0.5832 0.083(2) 1.0000 Uiso H71 0.5926 0.1135 0.5665 0.083(2) 1.0000 Uiso H72 0.5593 0.1415 0.4869 0.083(2) 1.0000 Uiso H73 0.6115 0.0750 0.4726 0.083(2) 1.0000 Uiso H131 0.5665 0.0477 1.0920 0.083(2) 1.0000 Uiso H141 0.3971 0.1100 1.0513 0.083(2) 1.0000 Uiso H151 0.3458 0.1573 0.9172 0.083(2) 1.0000 Uiso H161 0.4926 0.1463 0.8344 0.083(2) 1.0000 Uiso H171 0.7781 0.0276 1.1330 0.083(2) 1.0000 Uiso H172 0.6867 -0.0187 1.0924 0.083(2) 1.0000 Uiso H173 0.8344 -0.0222 1.0840 0.083(2) 1.0000 Uiso H1021 1.1238 0.1001 0.4514 0.083(2) 1.0000 Uiso H1022 1.2108 0.1578 0.4945 0.083(2) 1.0000 Uiso H1031 1.3399 0.0763 0.5217 0.083(2) 1.0000 Uiso H1041 1.4080 0.0881 0.6733 0.083(2) 1.0000 Uiso H1042 1.3802 0.1418 0.6295 0.083(2) 1.0000 Uiso H1051 1.2707 0.1394 0.7381 0.083(2) 1.0000 Uiso H1061 1.1100 0.0739 0.7345 0.083(2) 1.0000 Uiso H1062 1.2463 0.0435 0.7363 0.083(2) 1.0000 Uiso H1071 1.0713 0.0030 0.6284 0.083(2) 1.0000 Uiso H1081 0.9621 0.0610 0.5128 0.083(2) 1.0000 Uiso H1082 0.9454 0.0890 0.6056 0.083(2) 1.0000 Uiso H1091 1.0607 0.1683 0.6647 0.083(2) 1.0000 Uiso H1092 1.1663 0.1942 0.6226 0.083(2) 1.0000 Uiso H1101 1.2671 0.0054 0.6005 0.083(2) 1.0000 Uiso H1102 1.1615 0.0169 0.5098 0.083(2) 1.0000 Uiso H2021 1.0250 0.2295 0.3712 0.083(2) 1.0000 Uiso H2022 1.0801 0.1701 0.3671 0.083(2) 1.0000 Uiso H2031 0.9962 0.1989 0.2336 0.083(2) 1.0000 Uiso H2041 0.9523 0.1063 0.2316 0.083(2) 1.0000 Uiso H2042 0.8367 0.1330 0.1670 0.083(2) 1.0000 Uiso H2051 0.7618 0.0765 0.2622 0.083(2) 1.0000 Uiso H2061 0.6355 0.1530 0.2004 0.083(2) 1.0000 Uiso H2062 0.6129 0.1456 0.3001 0.083(2) 1.0000 Uiso H2071 0.6509 0.2348 0.2797 0.083(2) 1.0000 Uiso H2081 0.7280 0.2025 0.4147 0.083(2) 1.0000 Uiso H2082 0.8321 0.2456 0.4062 0.083(2) 1.0000 Uiso H2091 0.9401 0.0937 0.3752 0.083(2) 1.0000 Uiso H2092 0.7938 0.1052 0.4055 0.083(2) 1.0000 Uiso H2101 0.7732 0.2297 0.1780 0.083(2) 1.0000 Uiso H2102 0.8376 0.2673 0.2649 0.083(2) 1.0000 Uiso H3021 0.8595 0.1560 0.7873 0.083(2) 1.0000 Uiso H3022 0.9597 0.1081 0.8314 0.083(2) 1.0000 Uiso H3031 1.0705 0.1878 0.8422 0.083(2) 1.0000 Uiso H3041 1.0185 0.2669 0.9034 0.083(2) 1.0000 Uiso H3042 0.9027 0.2477 0.8240 0.083(2) 1.0000 Uiso H3051 0.8112 0.2691 0.9407 0.083(2) 1.0000 Uiso H3061 0.8756 0.2177 1.0655 0.083(2) 1.0000 Uiso H3062 1.0069 0.2452 1.0499 0.083(2) 1.0000 Uiso H3071 1.0543 0.1548 1.0787 0.083(2) 1.0000 Uiso H3081 0.9516 0.0850 0.9766 0.083(2) 1.0000 Uiso H3082 0.8424 0.1184 1.0243 0.083(2) 1.0000 Uiso H3091 0.7043 0.1871 0.9444 0.083(2) 1.0000 Uiso H3092 0.7042 0.2015 0.8435 0.083(2) 1.0000 Uiso H3101 1.1532 0.1975 0.9804 0.083(2) 1.0000 Uiso H3102 1.1264 0.1323 0.9501 0.083(2) 1.0000 Uiso H4021 0.8117 0.0753 0.7288 0.083(2) 1.0000 Uiso H4022 0.6423 0.0716 0.6975 0.083(2) 1.0000 Uiso H4031 0.7409 0.0118 0.6181 0.083(2) 1.0000 Uiso H4041 0.9405 -0.0049 0.7249 0.083(2) 1.0000 Uiso H4042 0.8756 -0.0609 0.6970 0.083(2) 1.0000 Uiso H4051 0.9446 -0.0636 0.8429 0.083(2) 1.0000 Uiso H4061 0.7479 -0.0898 0.8662 0.083(2) 1.0000 Uiso H4062 0.7378 -0.1129 0.7679 0.083(2) 1.0000 Uiso H4071 0.5443 -0.0730 0.7637 0.083(2) 1.0000 Uiso H4081 0.6125 -0.0092 0.8734 0.083(2) 1.0000 Uiso H4082 0.5296 0.0236 0.7853 0.083(2) 1.0000 Uiso H4091 0.9325 0.0315 0.8657 0.083(2) 1.0000 Uiso H4092 0.8485 -0.0001 0.9175 0.083(2) 1.0000 Uiso H4101 0.5507 -0.0088 0.6452 0.083(2) 1.0000 Uiso H4102 0.6341 -0.0665 0.6447 0.083(2) 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 O1 0.055(2) 0.070(2) 0.076(2) -0.003(2) 0.017(1) -0.001(1) O11 0.064(2) 0.059(2) 0.054(2) 0.015(1) 0.024(1) 0.003(1) C1 0.057(2) 0.055(3) 0.041(2) -0.001(2) 0.003(2) 0.018(2) C2 0.060(2) 0.069(3) 0.043(2) 0.007(2) 0.007(2) 0.023(2) C3 0.074(3) 0.093(4) 0.041(2) 0.011(2) 0.013(2) 0.035(3) C4 0.105(4) 0.106(5) 0.047(3) -0.002(3) 0.014(3) 0.060(4) C5 0.108(4) 0.084(4) 0.053(3) -0.016(2) -0.010(3) 0.037(3) C6 0.077(3) 0.059(3) 0.048(2) -0.006(2) -0.002(2) 0.018(2) C7 0.054(3) 0.107(4) 0.084(3) 0.012(3) 0.014(2) -0.011(3) C10 0.045(2) 0.040(2) 0.053(2) -0.002(2) 0.008(2) 0.001(2) C11 0.043(2) 0.039(2) 0.047(2) -0.006(2) 0.018(2) -0.005(2) C12 0.047(2) 0.045(2) 0.053(2) -0.005(2) 0.021(2) -0.013(2) C13 0.071(3) 0.063(3) 0.071(3) -0.008(2) 0.043(2) -0.015(2) C14 0.076(3) 0.083(3) 0.099(4) -0.019(3) 0.062(3) -0.011(3) C15 0.052(3) 0.064(3) 0.115(4) -0.014(3) 0.039(3) -0.003(2) C16 0.042(2) 0.051(2) 0.068(2) -0.010(2) 0.018(2) -0.003(2) C17 0.093(3) 0.065(3) 0.057(2) 0.008(2) 0.018(2) -0.006(2) C20 0.038(2) 0.041(2) 0.040(2) 0.004(1) 0.014(1) 0.002(2) C101 0.043(2) 0.038(2) 0.043(2) -0.003(2) 0.004(1) 0.003(2) C102 0.047(2) 0.053(2) 0.081(3) 0.014(2) 0.020(2) 0.003(2) C103 0.050(2) 0.075(3) 0.079(3) 0.016(2) 0.022(2) 0.016(2) C104 0.048(2) 0.073(3) 0.124(4) 0.022(3) -0.011(3) -0.005(2) C105 0.064(3) 0.072(3) 0.063(3) -0.016(2) -0.014(2) 0.010(2) C106 0.077(3) 0.071(3) 0.056(3) 0.009(2) 0.006(2) 0.017(2) C107 0.066(3) 0.045(2) 0.064(2) 0.010(2) 0.015(2) 0.003(2) C108 0.055(2) 0.042(2) 0.059(2) 0.003(2) 0.008(2) -0.001(2) C109 0.067(3) 0.048(2) 0.072(3) -0.009(2) -0.013(2) 0.005(2) C110 0.064(2) 0.050(3) 0.074(3) 0.007(2) 0.016(2) 0.017(2) C201 0.041(2) 0.043(2) 0.040(2) -0.001(1) 0.009(1) 0.006(2) C202 0.064(3) 0.078(3) 0.072(3) 0.021(2) 0.023(2) 0.003(2) C203 0.074(3) 0.109(4) 0.057(3) 0.028(3) 0.034(2) 0.024(3) C204 0.116(4) 0.082(3) 0.053(3) 0.004(2) 0.028(3) 0.055(3) C205 0.104(3) 0.056(3) 0.052(2) -0.014(2) 0.010(2) 0.009(2) C206 0.078(3) 0.089(4) 0.051(2) -0.007(2) -0.004(2) 0.015(3) C207 0.071(3) 0.068(3) 0.048(2) -0.001(2) 0.010(2) 0.032(2) C208 0.061(2) 0.061(3) 0.050(2) -0.005(2) 0.009(2) 0.021(2) C209 0.074(3) 0.043(2) 0.045(2) -0.006(2) 0.012(2) 0.005(2) C210 0.105(4) 0.068(3) 0.064(3) 0.019(2) 0.019(3) 0.033(3) C301 0.037(2) 0.045(2) 0.036(2) 0.000(1) 0.010(1) -0.007(2) C302 0.053(2) 0.056(2) 0.047(2) 0.001(2) 0.019(2) -0.010(2) C303 0.065(3) 0.071(3) 0.065(3) -0.005(2) 0.035(2) -0.028(2) C304 0.079(3) 0.051(3) 0.066(2) 0.002(2) 0.016(2) -0.021(2) C305 0.057(2) 0.051(3) 0.065(2) -0.007(2) 0.016(2) -0.008(2) C306 0.062(3) 0.071(3) 0.057(2) -0.016(2) 0.017(2) -0.020(2) C307 0.050(2) 0.076(3) 0.049(2) 0.003(2) 0.005(2) -0.011(2) C308 0.047(2) 0.058(2) 0.043(2) 0.006(2) 0.010(2) -0.010(2) C309 0.054(2) 0.044(2) 0.060(2) -0.007(2) 0.012(2) -0.002(2) C310 0.044(2) 0.078(3) 0.081(3) -0.008(2) 0.014(2) -0.016(2) C401 0.039(2) 0.037(2) 0.043(2) -0.002(1) 0.015(1) 0.000(2) C402 0.065(2) 0.052(2) 0.044(2) -0.002(2) 0.014(2) 0.001(2) C403 0.078(3) 0.055(2) 0.046(2) -0.007(2) 0.021(2) 0.002(2) C404 0.087(3) 0.056(3) 0.070(3) -0.006(2) 0.041(2) 0.011(2) C405 0.069(3) 0.050(2) 0.064(2) 0.007(2) 0.027(2) 0.016(2) C406 0.093(3) 0.040(2) 0.092(3) -0.002(2) 0.045(3) 0.000(2) C407 0.070(3) 0.055(3) 0.088(3) -0.023(2) 0.033(2) -0.019(2) C408 0.052(2) 0.047(2) 0.069(3) -0.015(2) 0.025(2) -0.010(2) C409 0.050(2) 0.047(2) 0.050(2) 0.008(2) 0.021(2) 0.011(2) C410 0.094(4) 0.066(3) 0.074(3) -0.032(2) 0.016(3) -0.001(3) _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 O1 . C2 . 1.379(5) yes O1 . C7 . 1.410(5) yes O11 . C12 . 1.372(4) yes O11 . C17 . 1.417(5) yes C1 . C2 . 1.385(6) yes C1 . C6 . 1.378(5) yes C1 . C10 . 1.533(5) yes C2 . C3 . 1.399(6) yes C3 . C4 . 1.362(7) yes C3 . H31 . 1.105(5) no C4 . C5 . 1.378(8) yes C4 . H41 . 0.988(5) no C5 . C6 . 1.375(7) yes C5 . H51 . 1.043(6) no C6 . H61 . 1.084(5) no C7 . H71 . 1.046(5) no C7 . H72 . 1.020(5) no C7 . H73 . 1.065(5) no C10 . C101 . 1.594(5) yes C10 . C201 . 1.585(5) yes C10 . H10 . 1.126(3) no C11 . C12 . 1.394(5) yes C11 . C16 . 1.388(5) yes C11 . C20 . 1.544(4) yes C12 . C13 . 1.383(5) yes C13 . C14 . 1.388(7) yes C13 . H131 . 1.019(4) no C14 . C15 . 1.359(7) yes C14 . H141 . 0.913(4) no C15 . C16 . 1.382(6) yes C15 . H151 . 1.068(5) no C16 . H161 . 1.052(4) no C17 . H171 . 0.954(4) no C17 . H172 . 1.008(5) no C17 . H173 . 1.055(5) no C20 . C301 . 1.584(4) yes C20 . C401 . 1.584(5) yes C20 . H20 . 1.042(3) no C101 . C102 . 1.540(5) yes C101 . C108 . 1.519(5) yes C101 . C109 . 1.543(5) yes C102 . C103 . 1.543(5) yes C102 . H1021 . 1.033(4) no C102 . H1022 . 1.022(4) no C103 . C104 . 1.519(7) yes C103 . C110 . 1.503(6) yes C103 . H1031 . 1.029(4) no C104 . C105 . 1.520(7) yes C104 . H1041 . 1.045(4) no C104 . H1042 . 0.943(5) no C105 . C106 . 1.507(7) yes C105 . C109 . 1.539(6) yes C105 . H1051 . 0.981(4) no C106 . C107 . 1.517(6) yes C106 . H1061 . 1.026(5) no C106 . H1062 . 1.071(4) no C107 . C108 . 1.544(5) yes C107 . C110 . 1.517(6) yes C107 . H1071 . 1.141(4) no C108 . H1081 . 1.034(4) no C108 . H1082 . 1.088(4) no C109 . H1091 . 1.081(5) no C109 . H1092 . 1.002(4) no C110 . H1101 . 0.980(4) no C110 . H1102 . 1.074(4) no C201 . C202 . 1.549(5) yes C201 . C208 . 1.539(5) yes C201 . C209 . 1.531(5) yes C202 . C203 . 1.536(6) yes C202 . H2021 . 1.052(5) no C202 . H2022 . 1.050(4) no C203 . C204 . 1.522(7) yes C203 . C210 . 1.534(6) yes C203 . H2031 . 0.937(4) no C204 . C205 . 1.498(7) yes C204 . H2041 . 1.045(4) no C204 . H2042 . 1.026(4) no C205 . C206 . 1.505(6) yes C205 . C209 . 1.534(5) yes C205 . H2051 . 1.073(4) no C206 . C207 . 1.511(7) yes C206 . H2061 . 1.007(4) no C206 . H2062 . 1.099(5) no C207 . C208 . 1.538(5) yes C207 . C210 . 1.496(6) yes C207 . H2071 . 1.007(4) no C208 . H2081 . 0.980(4) no C208 . H2082 . 1.054(4) no C209 . H2091 . 1.037(4) no C209 . H2092 . 1.044(4) no C210 . H2101 . 1.008(5) no C210 . H2102 . 1.061(5) no C301 . C302 . 1.540(4) yes C301 . C308 . 1.528(5) yes C301 . C309 . 1.556(5) yes C302 . C303 . 1.526(5) yes C302 . H3021 . 0.950(4) no C302 . H3022 . 1.062(4) no C303 . C304 . 1.525(6) yes C303 . C310 . 1.520(6) yes C303 . H3031 . 0.934(4) no C304 . C305 . 1.511(6) yes C304 . H3041 . 1.020(4) no C304 . H3042 . 0.977(4) no C305 . C306 . 1.504(6) yes C305 . C309 . 1.526(5) yes C305 . H3051 . 1.075(4) no C306 . C307 . 1.516(6) yes C306 . H3061 . 1.083(4) no C306 . H3062 . 1.062(4) no C307 . C308 . 1.536(5) yes C307 . C310 . 1.514(6) yes C307 . H3071 . 1.044(4) no C308 . H3081 . 1.082(4) no C308 . H3082 . 1.030(3) no C309 . H3091 . 1.037(4) no C309 . H3092 . 1.068(4) no C310 . H3101 . 1.011(4) no C310 . H3102 . 1.031(5) no C401 . C402 . 1.551(5) yes C401 . C408 . 1.539(5) yes C401 . C409 . 1.522(5) yes C402 . C403 . 1.533(5) yes C402 . H4021 . 1.032(4) no C402 . H4022 . 1.100(4) no C403 . C404 . 1.500(6) yes C403 . C410 . 1.529(6) yes C403 . H4031 . 1.030(4) no C404 . C405 . 1.534(6) yes C404 . H4041 . 1.029(5) no C404 . H4042 . 0.942(4) no C405 . C406 . 1.522(6) yes C405 . C409 . 1.531(5) yes C405 . H4051 . 1.092(4) no C406 . C407 . 1.518(6) yes C406 . H4061 . 0.992(4) no C406 . H4062 . 1.108(4) no C407 . C408 . 1.539(5) yes C407 . C410 . 1.524(6) yes C407 . H4071 . 1.083(4) no C408 . H4081 . 1.073(4) no C408 . H4082 . 1.039(4) no C409 . H4091 . 1.046(4) no C409 . H4092 . 0.988(3) no C410 . H4101 . 1.083(5) no C410 . H4102 . 0.981(4) 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 . O1 . C7 . 119.5(3) no C12 . O11 . C17 . 119.2(3) no C2 . C1 . C6 . 116.9(4) no C2 . C1 . C10 . 126.0(3) no C6 . C1 . C10 . 117.1(4) no O1 . C2 . C1 . 117.8(3) no O1 . C2 . C3 . 120.7(4) no C1 . C2 . C3 . 121.5(4) no C2 . C3 . C4 . 118.5(5) no C2 . C3 . H31 . 111.2(4) no C4 . C3 . H31 . 130.2(5) no C3 . C4 . C5 . 122.1(4) no C3 . C4 . H41 . 118.6(7) no C5 . C4 . H41 . 119.2(7) no C4 . C5 . C6 . 117.6(5) no C4 . C5 . H51 . 133.9(6) no C6 . C5 . H51 . 108.4(6) no C1 . C6 . C5 . 123.4(5) no C1 . C6 . H61 . 120.6(4) no C5 . C6 . H61 . 116.0(4) no O1 . C7 . H71 . 105.8(4) no O1 . C7 . H72 . 109.9(4) no H71 . C7 . H72 . 89.4(4) no O1 . C7 . H73 . 105.2(4) no H71 . C7 . H73 . 126.2(5) no H72 . C7 . H73 . 119.0(4) no C1 . C10 . C101 . 111.1(3) no C1 . C10 . C201 . 114.7(3) no C101 . C10 . C201 . 121.4(3) no C1 . C10 . H10 . 104.8(3) no C101 . C10 . H10 . 97.5(3) no C201 . C10 . H10 . 103.8(3) no C12 . C11 . C16 . 116.7(3) no C12 . C11 . C20 . 126.2(3) no C16 . C11 . C20 . 117.0(3) no O11 . C12 . C11 . 116.6(3) no O11 . C12 . C13 . 121.8(4) no C11 . C12 . C13 . 121.6(4) no C12 . C13 . C14 . 119.0(4) no C12 . C13 . H131 . 116.8(4) no C14 . C13 . H131 . 123.9(4) no C13 . C14 . C15 . 120.9(4) no C13 . C14 . H141 . 117.8(6) no C15 . C14 . H141 . 121.2(6) no C14 . C15 . C16 . 119.1(4) no C14 . C15 . H151 . 125.2(4) no C16 . C15 . H151 . 115.6(5) no C11 . C16 . C15 . 122.4(4) no C11 . C16 . H161 . 117.2(3) no C15 . C16 . H161 . 120.4(4) no O11 . C17 . H171 . 112.5(4) no O11 . C17 . H172 . 112.1(4) no H171 . C17 . H172 . 106.1(4) no O11 . C17 . H173 . 104.8(3) no H171 . C17 . H173 . 114.2(4) no H172 . C17 . H173 . 107.1(4) no C11 . C20 . C301 . 110.3(3) no C11 . C20 . C401 . 114.8(3) no C301 . C20 . C401 . 121.5(3) no C11 . C20 . H20 . 100.7(3) no C301 . C20 . H20 . 100.1(3) no C401 . C20 . H20 . 105.9(3) no C10 . C101 . C102 . 110.6(3) no C10 . C101 . C108 . 116.5(3) no C102 . C101 . C108 . 109.1(3) no C10 . C101 . C109 . 106.1(3) no C102 . C101 . C109 . 106.9(3) no C108 . C101 . C109 . 107.2(3) no C101 . C102 . C103 . 111.5(3) no C101 . C102 . H1021 . 103.3(3) no C103 . C102 . H1021 . 105.4(3) no C101 . C102 . H1022 . 107.3(3) no C103 . C102 . H1022 . 109.4(3) no H1021 . C102 . H1022 . 119.8(4) no C102 . C103 . C104 . 108.8(4) no C102 . C103 . C110 . 108.7(3) no C104 . C103 . C110 . 110.0(4) no C102 . C103 . H1031 . 110.4(4) no C104 . C103 . H1031 . 110.3(4) no C110 . C103 . H1031 . 108.7(4) no C103 . C104 . C105 . 109.4(3) no C103 . C104 . H1041 . 112.1(5) no C105 . C104 . H1041 . 109.5(5) no C103 . C104 . H1042 . 111.6(5) no C105 . C104 . H1042 . 114.2(5) no H1041 . C104 . H1042 . 99.9(4) no C104 . C105 . C106 . 110.5(4) no C104 . C105 . C109 . 108.7(4) no C106 . C105 . C109 . 109.1(4) no C104 . C105 . H1051 . 111.9(4) no C106 . C105 . H1051 . 111.1(4) no C109 . C105 . H1051 . 105.3(4) no C105 . C106 . C107 . 109.7(3) no C105 . C106 . H1061 . 112.3(4) no C107 . C106 . H1061 . 110.3(4) no C105 . C106 . H1062 . 108.1(4) no C107 . C106 . H1062 . 110.9(4) no H1061 . C106 . H1062 . 105.6(4) no C106 . C107 . C108 . 109.0(3) no C106 . C107 . C110 . 108.9(4) no C108 . C107 . C110 . 110.3(3) no C106 . C107 . H1071 . 108.8(3) no C108 . C107 . H1071 . 111.9(3) no C110 . C107 . H1071 . 107.9(3) no C101 . C108 . C107 . 110.6(3) no C101 . C108 . H1081 . 113.7(3) no C107 . C108 . H1081 . 107.2(3) no C101 . C108 . H1082 . 108.8(3) no C107 . C108 . H1082 . 106.3(3) no H1081 . C108 . H1082 . 109.9(3) no C101 . C109 . C105 . 111.4(3) no C101 . C109 . H1091 . 106.8(3) no C105 . C109 . H1091 . 113.6(4) no C101 . C109 . H1092 . 107.3(4) no C105 . C109 . H1092 . 114.4(4) no H1091 . C109 . H1092 . 102.7(4) no C103 . C110 . C107 . 110.6(3) no C103 . C110 . H1101 . 117.0(4) no C107 . C110 . H1101 . 105.8(4) no C103 . C110 . H1102 . 108.8(4) no C107 . C110 . H1102 . 105.4(3) no H1101 . C110 . H1102 . 108.7(4) no C10 . C201 . C202 . 109.2(3) no C10 . C201 . C208 . 109.1(3) no C202 . C201 . C208 . 106.0(3) no C10 . C201 . C209 . 117.3(3) no C202 . C201 . C209 . 106.5(3) no C208 . C201 . C209 . 108.1(3) no C201 . C202 . C203 . 111.7(3) no C201 . C202 . H2021 . 108.0(4) no C203 . C202 . H2021 . 111.0(4) no C201 . C202 . H2022 . 111.4(3) no C203 . C202 . H2022 . 113.8(4) no H2021 . C202 . H2022 . 100.4(4) no C202 . C203 . C204 . 110.2(4) no C202 . C203 . C210 . 109.1(4) no C204 . C203 . C210 . 108.5(4) no C202 . C203 . H2031 . 102.0(4) no C204 . C203 . H2031 . 109.5(5) no C210 . C203 . H2031 . 117.3(4) no C203 . C204 . C205 . 109.6(3) no C203 . C204 . H2041 . 114.6(5) no C205 . C204 . H2041 . 111.7(4) no C203 . C204 . H2042 . 112.0(4) no C205 . C204 . H2042 . 108.8(5) no H2041 . C204 . H2042 . 99.6(3) no C204 . C205 . C206 . 109.4(4) no C204 . C205 . C209 . 109.3(4) no C206 . C205 . C209 . 111.1(3) no C204 . C205 . H2051 . 109.6(4) no C206 . C205 . H2051 . 111.1(4) no C209 . C205 . H2051 . 106.2(4) no C205 . C206 . C207 . 109.1(4) no C205 . C206 . H2061 . 109.2(4) no C207 . C206 . H2061 . 110.0(4) no C205 . C206 . H2062 . 113.6(4) no C207 . C206 . H2062 . 103.6(4) no H2061 . C206 . H2062 . 111.1(4) no C206 . C207 . C208 . 108.1(3) no C206 . C207 . C210 . 111.1(4) no C208 . C207 . C210 . 110.1(4) no C206 . C207 . H2071 . 110.1(4) no C208 . C207 . H2071 . 106.1(3) no C210 . C207 . H2071 . 111.1(4) no C201 . C208 . C207 . 112.2(3) no C201 . C208 . H2081 . 112.9(3) no C207 . C208 . H2081 . 111.4(4) no C201 . C208 . H2082 . 100.3(3) no C207 . C208 . H2082 . 115.3(4) no H2081 . C208 . H2082 . 104.0(3) no C201 . C209 . C205 . 111.2(3) no C201 . C209 . H2091 . 106.3(3) no C205 . C209 . H2091 . 104.4(3) no C201 . C209 . H2092 . 104.8(3) no C205 . C209 . H2092 . 108.3(4) no H2091 . C209 . H2092 . 121.9(4) no C203 . C210 . C207 . 108.7(3) no C203 . C210 . H2101 . 110.8(4) no C207 . C210 . H2101 . 110.0(5) no C203 . C210 . H2102 . 114.2(5) no C207 . C210 . H2102 . 100.9(4) no H2101 . C210 . H2102 . 111.7(4) no C20 . C301 . C302 . 112.9(3) no C20 . C301 . C308 . 115.4(3) no C302 . C301 . C308 . 108.6(3) no C20 . C301 . C309 . 106.7(3) no C302 . C301 . C309 . 105.7(3) no C308 . C301 . C309 . 107.0(3) no C301 . C302 . C303 . 111.6(3) no C301 . C302 . H3021 . 106.4(3) no C303 . C302 . H3021 . 108.8(3) no C301 . C302 . H3022 . 112.9(3) no C303 . C302 . H3022 . 105.6(3) no H3021 . C302 . H3022 . 111.6(3) no C302 . C303 . C304 . 110.0(3) no C302 . C303 . C310 . 110.4(3) no C304 . C303 . C310 . 108.9(3) no C302 . C303 . H3031 . 112.0(4) no C304 . C303 . H3031 . 110.0(4) no C310 . C303 . H3031 . 105.4(4) no C303 . C304 . C305 . 108.3(3) no C303 . C304 . H3041 . 110.4(4) no C305 . C304 . H3041 . 110.8(4) no C303 . C304 . H3042 . 106.1(4) no C305 . C304 . H3042 . 109.9(4) no H3041 . C304 . H3042 . 111.1(4) no C304 . C305 . C306 . 109.8(3) no C304 . C305 . C309 . 111.0(3) no C306 . C305 . C309 . 108.6(3) no C304 . C305 . H3051 . 112.2(4) no C306 . C305 . H3051 . 110.3(3) no C309 . C305 . H3051 . 104.7(3) no C305 . C306 . C307 . 109.6(3) no C305 . C306 . H3061 . 109.2(4) no C307 . C306 . H3061 . 115.5(4) no C305 . C306 . H3062 . 111.2(4) no C307 . C306 . H3062 . 108.7(4) no H3061 . C306 . H3062 . 102.4(3) no C306 . C307 . C308 . 109.4(3) no C306 . C307 . C310 . 109.7(4) no C308 . C307 . C310 . 109.6(3) no C306 . C307 . H3071 . 106.4(3) no C308 . C307 . H3071 . 112.6(3) no C310 . C307 . H3071 . 109.0(3) no C301 . C308 . C307 . 111.3(3) no C301 . C308 . H3081 . 106.1(3) no C307 . C308 . H3081 . 105.9(3) no C301 . C308 . H3082 . 109.3(3) no C307 . C308 . H3082 . 107.6(3) no H3081 . C308 . H3082 . 116.6(3) no C301 . C309 . C305 . 111.6(3) no C301 . C309 . H3091 . 107.2(3) no C305 . C309 . H3091 . 109.6(3) no C301 . C309 . H3092 . 108.0(3) no C305 . C309 . H3092 . 111.9(3) no H3091 . C309 . H3092 . 108.4(3) no C303 . C310 . C307 . 109.1(3) no C303 . C310 . H3101 . 106.0(4) no C307 . C310 . H3101 . 111.5(4) no C303 . C310 . H3102 . 102.9(4) no C307 . C310 . H3102 . 112.7(4) no H3101 . C310 . H3102 . 114.1(4) no C20 . C401 . C402 . 107.2(3) no C20 . C401 . C408 . 109.3(3) no C402 . C401 . C408 . 105.4(3) no C20 . C401 . C409 . 117.7(3) no C402 . C401 . C409 . 107.9(3) no C408 . C401 . C409 . 108.8(3) no C401 . C402 . C403 . 112.1(3) no C401 . C402 . H4021 . 106.8(3) no C403 . C402 . H4021 . 108.6(3) no C401 . C402 . H4022 . 105.4(3) no C403 . C402 . H4022 . 109.4(3) no H4021 . C402 . H4022 . 114.6(3) no C402 . C403 . C404 . 109.5(3) no C402 . C403 . C410 . 108.3(3) no C404 . C403 . C410 . 110.1(4) no C402 . C403 . H4031 . 106.5(3) no C404 . C403 . H4031 . 114.2(3) no C410 . C403 . H4031 . 108.1(4) no C403 . C404 . C405 . 109.9(3) no C403 . C404 . H4041 . 110.5(4) no C405 . C404 . H4041 . 107.7(4) no C403 . C404 . H4042 . 114.7(4) no C405 . C404 . H4042 . 106.4(4) no H4041 . C404 . H4042 . 107.3(4) no C404 . C405 . C406 . 108.3(4) no C404 . C405 . C409 . 109.7(3) no C406 . C405 . C409 . 110.4(3) no C404 . C405 . H4051 . 109.4(3) no C406 . C405 . H4051 . 108.5(3) no C409 . C405 . H4051 . 110.5(3) no C405 . C406 . C407 . 109.4(3) no C405 . C406 . H4061 . 109.0(4) no C407 . C406 . H4061 . 114.1(4) no C405 . C406 . H4062 . 115.4(4) no C407 . C406 . H4062 . 100.8(4) no H4061 . C406 . H4062 . 108.1(4) no C406 . C407 . C408 . 110.7(3) no C406 . C407 . C410 . 109.3(4) no C408 . C407 . C410 . 108.2(4) no C406 . C407 . H4071 . 109.6(4) no C408 . C407 . H4071 . 110.5(3) no C410 . C407 . H4071 . 108.5(4) no C401 . C408 . C407 . 111.6(3) no C401 . C408 . H4081 . 110.2(3) no C407 . C408 . H4081 . 102.4(3) no C401 . C408 . H4082 . 112.9(3) no C407 . C408 . H4082 . 110.4(3) no H4081 . C408 . H4082 . 108.8(3) no C401 . C409 . C405 . 111.4(3) no C401 . C409 . H4091 . 113.8(3) no C405 . C409 . H4091 . 108.2(3) no C401 . C409 . H4092 . 110.5(3) no C405 . C409 . H4092 . 107.7(3) no H4091 . C409 . H4092 . 105.0(3) no C403 . C410 . C407 . 109.3(3) no C403 . C410 . H4101 . 102.9(4) no C407 . C410 . H4101 . 113.0(4) no C403 . C410 . H4102 . 108.4(4) no C407 . C410 . H4102 . 110.9(4) no H4101 . C410 . H4102 . 111.9(4) no