# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/246 data_CRYSTALS_cif _audit_creation_date 99-03-12 _audit_creation_method CRYSTALS # LOMAS13 #**************************************************************************** # 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 Institut de Topologie et de Dynamique des Systemes Universite de Paris 7, associe au CNRS, 1 rue Guy de la Brosse, 75005 Paris, France' ; _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 ; ; #============================================================================= # 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 ; Trifluoroacetylation and ionic hydrogenation of [2-(3-alkoxythienyl)]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. loop_ _publ_author_name _publ_author_address 'Lomas , John S.' ; Institut de Topologie et de Dynamique des Systemes Universite de Paris 7, associe au CNRS, 1 rue Guy de la Brosse, 75005 Paris, France ; 'Edouard Vauthier' ; Institut de Topologie et de Dynamique des Systemes Universite de Paris 7, associe au CNRS, 1 rue Guy de la Brosse, 75005 Paris, France ; 'Vaissermann, Jecqueline' ; Laboratoire de Chimie des Metaux de Transition, Universite de Paris 6, associe au CNRS, Case 42, 4 place Jussieu, 75252 Paris Cedex 05, France ; #============================================================================== # 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 ; _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 '167 C' _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-(3-methoxythienyl)]di(1-adamantyl)methanol' ; _cell_length_a 6.804(3) _cell_angle_alpha 70.85(2) _cell_length_b 11.122(2) _cell_angle_beta 86.12(3) _cell_length_c 15.139(2) _cell_angle_gamma 79.57(3) _cell_volume 1064.3(6) _symmetry_cell_setting 'Triclinic ' _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,-y,-z' 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' 'S ' 0.1100 0.1240 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International_Tables_Vol_IV_Table_2.2B' _chemical_formula_sum ' C26 H36 S1 O2 ' _chemical_formula_moiety ' C26 H36 S1 O2 ' _chemical_compound_source ; laboratory synthesis, crystallized from hexane ; _chemical_formula_weight 412.63 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 14.9 _cell_measurement_theta_max 15.2 _cell_measurement_temperature 295K _cell_formula_units_Z 2 _exptl_crystal_description ' prism ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.44 _exptl_crystal_size_mid 0.56 _exptl_crystal_size_max 0.60 _exptl_crystal_density_diffrn 1.29 _exptl_crystal_density_meas ? _exptl_crystal_F_000 448.31 _exptl_absorpt_coefficient_mu 0.16 _exptl_absorpt_correction_type 'none' _diffrn_standards_interval_time 3600s _diffrn_standards_number 2 _diffrn_standards_decay_% 4.39 _diffrn_ambient_temperature 295K _diffrn_reflns_number 6690 _reflns_number_total 6203 _diffrn_reflns_av_R_equivalents 0.01 _reflns_number_observed 4203 _diffrn_reflns_theta_min 1 _diffrn_reflns_theta_max 30 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min -14 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _reflns_observed_criterion >3.00\s(I) _refine_diff_density_min -0.25 _refine_diff_density_max 0.30 _refine_ls_number_reflns 4203 _refine_ls_number_parameters 263 _refine_ls_R_factor_obs 0.0429 _refine_ls_wR_factor_obs 0.0525 _refine_ls_goodness_of_fit_obs 1.0703 _refine_ls_shift/esd_max 0.852176 _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 S1 0.43658(5) 0.27331(5) 0.87388(3) 0.0425 1.0000 Uani O1 0.8438(2) 0.3664(2) 0.98987(8) 0.0498 1.0000 Uani O11 0.9863(1) 0.3731(1) 0.82337(7) 0.0335 1.0000 Uani C2 0.6595(2) 0.3241(1) 0.87765(9) 0.0304 1.0000 Uani C3 0.6791(2) 0.3295(1) 0.96573(9) 0.0349 1.0000 Uani C4 0.5183(2) 0.2918(2) 1.0283(1) 0.0428 1.0000 Uani C5 0.3780(2) 0.2591(2) 0.9870(1) 0.0448 1.0000 Uani C6 0.8427(3) 0.3894(2) 1.0758(1) 0.0476 1.0000 Uani C10 0.8046(2) 0.3506(1) 0.79347(8) 0.0278 1.0000 Uani C101 0.8756(2) 0.2207(1) 0.76690(9) 0.0300 1.0000 Uani C102 1.0726(2) 0.2252(1) 0.7089(1) 0.0384 1.0000 Uani C103 1.1499(2) 0.0960(2) 0.6916(1) 0.0454 1.0000 Uani C104 1.1936(2) -0.0116(2) 0.7846(1) 0.0509 1.0000 Uani C105 1.0009(2) -0.0208(2) 0.8422(1) 0.0459 1.0000 Uani C106 0.8425(3) -0.0512(2) 0.7901(1) 0.0490 1.0000 Uani C107 0.8023(2) 0.0557(2) 0.6964(1) 0.0440 1.0000 Uani C108 0.7251(2) 0.1862(1) 0.7115(1) 0.0370 1.0000 Uani C109 0.9232(2) 0.1075(1) 0.8597(1) 0.0385 1.0000 Uani C110 0.9943(3) 0.0643(2) 0.6382(1) 0.0489 1.0000 Uani C201 0.7167(2) 0.4829(1) 0.71541(9) 0.0300 1.0000 Uani C202 0.8671(2) 0.5226(2) 0.6347(1) 0.0409 1.0000 Uani C203 0.7951(3) 0.6570(2) 0.5662(1) 0.0470 1.0000 Uani C204 0.6003(3) 0.6553(2) 0.5233(1) 0.0517 1.0000 Uani C205 0.4457(3) 0.6208(2) 0.6004(1) 0.0488 1.0000 Uani C206 0.4092(3) 0.7219(2) 0.6501(1) 0.0551 1.0000 Uani C207 0.6052(3) 0.7235(2) 0.6924(1) 0.0467 1.0000 Uani C208 0.6798(2) 0.5901(2) 0.7619(1) 0.0407 1.0000 Uani C209 0.5166(2) 0.4870(2) 0.6716(1) 0.0422 1.0000 Uani C210 0.7615(3) 0.7582(2) 0.6159(1) 0.0516 1.0000 Uani H11 0.9574 0.3891 0.8773 0.061(1) 1.0000 Uiso H41 0.5136 0.2936 1.0928 0.061(1) 1.0000 Uiso H51 0.2572 0.2285 1.0135 0.061(1) 1.0000 Uiso H61 0.9853 0.4062 1.0811 0.061(1) 1.0000 Uiso H62 0.7333 0.4533 1.0789 0.061(1) 1.0000 Uiso H63 0.8149 0.3192 1.1257 0.061(1) 1.0000 Uiso H1021 1.1766 0.2470 0.7444 0.061(1) 1.0000 Uiso H1022 1.0547 0.2890 0.6444 0.061(1) 1.0000 Uiso H1031 1.2730 0.1043 0.6551 0.061(1) 1.0000 Uiso H1041 1.3061 0.0073 0.8199 0.061(1) 1.0000 Uiso H1042 1.2461 -0.0954 0.7725 0.061(1) 1.0000 Uiso H1051 1.0241 -0.0869 0.9027 0.061(1) 1.0000 Uiso H1061 0.7171 -0.0569 0.8272 0.061(1) 1.0000 Uiso H1062 0.8874 -0.1343 0.7755 0.061(1) 1.0000 Uiso H1071 0.7059 0.0402 0.6575 0.061(1) 1.0000 Uiso H1081 0.5875 0.1853 0.7412 0.061(1) 1.0000 Uiso H1082 0.7028 0.2519 0.6481 0.061(1) 1.0000 Uiso H1091 1.0136 0.1298 0.8958 0.061(1) 1.0000 Uiso H1092 0.8036 0.0960 0.8989 0.061(1) 1.0000 Uiso H1101 1.0416 -0.0169 0.6211 0.061(1) 1.0000 Uiso H1102 0.9583 0.1329 0.5698 0.061(1) 1.0000 Uiso H2021 0.8825 0.4604 0.5963 0.061(1) 1.0000 Uiso H2022 0.9993 0.5205 0.6645 0.061(1) 1.0000 Uiso H2031 0.8966 0.6791 0.5184 0.061(1) 1.0000 Uiso H2041 0.5634 0.7408 0.4746 0.061(1) 1.0000 Uiso H2042 0.6325 0.5930 0.4859 0.061(1) 1.0000 Uiso H2051 0.3223 0.6220 0.5707 0.061(1) 1.0000 Uiso H2061 0.2978 0.6956 0.7025 0.061(1) 1.0000 Uiso H2062 0.3686 0.8079 0.6008 0.061(1) 1.0000 Uiso H2071 0.5858 0.7815 0.7282 0.061(1) 1.0000 Uiso H2081 0.5852 0.5677 0.8158 0.061(1) 1.0000 Uiso H2082 0.8029 0.5871 0.7931 0.061(1) 1.0000 Uiso H2091 0.5376 0.4266 0.6322 0.061(1) 1.0000 Uiso H2092 0.4085 0.4642 0.7270 0.061(1) 1.0000 Uiso H2101 0.8895 0.7576 0.6415 0.061(1) 1.0000 Uiso H2102 0.7182 0.8438 0.5710 0.061(1) 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 S1 0.0280(2) 0.0895(3) 0.0462(2) -0.0303(2) 0.0079(1) -0.0256(2) O1 0.0516(7) 0.122(1) 0.0401(6) -0.0437(7) 0.0086(5) -0.0417(7) O11 0.0223(4) 0.0654(7) 0.0384(5) -0.0260(5) 0.0002(3) -0.0149(4) C2 0.0226(5) 0.0433(7) 0.0307(6) -0.0132(5) 0.0009(4) -0.0079(5) C3 0.0313(6) 0.0464(8) 0.0306(6) -0.0133(5) 0.0010(5) -0.0082(5) C4 0.0425(7) 0.061(1) 0.0315(6) -0.0138(6) 0.0087(6) -0.0115(7) C5 0.0354(7) 0.065(1) 0.0447(8) -0.0146(7) 0.0147(6) -0.0149(7) C6 0.065(1) 0.060(1) 0.0341(7) -0.0202(7) -0.0036(7) -0.0162(8) C10 0.0210(5) 0.0422(7) 0.0297(5) -0.0157(5) -0.0004(4) -0.0087(4) C101 0.0250(5) 0.0391(7) 0.0297(5) -0.0127(5) 0.0002(4) -0.0073(5) C102 0.0329(6) 0.0446(8) 0.0444(7) -0.0182(6) 0.0102(5) -0.0095(6) C103 0.0403(7) 0.0505(9) 0.0555(9) -0.0237(7) 0.0149(7) -0.0060(6) C104 0.0390(8) 0.0518(9) 0.065(1) -0.0208(8) 0.0001(7) 0.0036(7) C105 0.0470(8) 0.0419(8) 0.0444(8) -0.0083(6) -0.0023(6) -0.0018(6) C106 0.0522(9) 0.0408(8) 0.0564(9) -0.0142(7) 0.0029(7) -0.0122(7) C107 0.0478(8) 0.0431(8) 0.0502(8) -0.0219(7) -0.0054(7) -0.0083(6) C108 0.0348(6) 0.0428(7) 0.0413(7) -0.0187(6) -0.0071(5) -0.0061(5) C109 0.0367(6) 0.0459(8) 0.0330(6) -0.0105(6) -0.0026(5) -0.0059(6) C110 0.063(1) 0.0465(9) 0.0469(8) -0.0235(7) 0.0061(7) -0.0055(7) C201 0.0286(5) 0.0382(6) 0.0296(5) -0.0150(5) -0.0002(4) -0.0089(5) C202 0.0436(7) 0.0464(8) 0.0342(6) -0.0125(6) 0.0061(6) -0.0086(6) C203 0.0594(9) 0.0479(9) 0.0365(7) -0.0103(6) 0.0083(7) -0.0135(7) C204 0.084(1) 0.0460(9) 0.0379(8) -0.0109(7) -0.0168(8) -0.0059(8) C205 0.0495(9) 0.0452(9) 0.060(1) -0.0128(7) -0.0219(8) -0.0051(7) C206 0.0521(9) 0.0467(9) 0.064(1) -0.0139(8) -0.0038(8) 0.0017(7) C207 0.062(1) 0.0415(8) 0.0485(8) -0.0235(7) 0.0024(7) -0.0079(7) C208 0.0501(8) 0.0458(8) 0.0374(7) -0.0222(6) 0.0027(6) -0.0096(6) C209 0.0405(7) 0.0413(8) 0.0541(9) -0.0116(6) -0.0175(6) -0.0083(6) C210 0.065(1) 0.0434(9) 0.0541(9) -0.0134(7) -0.0023(8) -0.0196(8) _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 S1 . C2 . 1.722(1) yes S1 . C5 . 1.694(2) yes O1 . C3 . 1.370(2) yes O1 . C6 . 1.405(2) yes O11 . C10 . 1.435(1) yes O11 . H11 . 0.8927(9) no C2 . C3 . 1.371(2) yes C2 . C10 . 1.541(2) yes C3 . C4 . 1.426(2) yes C4 . C5 . 1.337(2) yes C4 . H41 . 0.982(1) no C5 . H51 . 0.958(1) no C6 . H61 . 1.033(2) no C6 . H62 . 0.942(2) no C6 . H63 . 0.930(2) no C10 . C101 . 1.608(2) yes C10 . C201 . 1.599(2) yes C101 . C102 . 1.551(2) yes C101 . C108 . 1.539(2) yes C101 . C109 . 1.555(2) yes C102 . C103 . 1.538(2) yes C102 . H1021 . 1.023(2) no C102 . H1022 . 1.000(2) no C103 . C104 . 1.525(3) yes C103 . C110 . 1.528(3) yes C103 . H1031 . 0.973(1) no C104 . C105 . 1.525(2) yes C104 . H1041 . 1.051(2) no C104 . H1042 . 1.005(2) no C105 . C106 . 1.523(2) yes C105 . C109 . 1.530(2) yes C105 . H1051 . 0.970(2) no C106 . C107 . 1.526(2) yes C106 . H1061 . 0.989(2) no C106 . H1062 . 1.009(2) no C107 . C108 . 1.536(2) yes C107 . C110 . 1.525(2) yes C107 . H1071 . 0.982(2) no C108 . H1081 . 1.011(1) no C108 . H1082 . 0.999(1) no C109 . H1091 . 0.964(1) no C109 . H1092 . 0.976(1) no C110 . H1101 . 1.011(2) no C110 . H1102 . 1.079(2) no C201 . C202 . 1.541(2) yes C201 . C208 . 1.548(2) yes C201 . C209 . 1.541(2) yes C202 . C203 . 1.529(2) yes C202 . H2021 . 1.027(2) no C202 . H2022 . 1.026(2) no C203 . C204 . 1.520(3) yes C203 . C210 . 1.525(3) yes C203 . H2031 . 0.969(2) no C204 . C205 . 1.517(3) yes C204 . H2041 . 0.995(2) no C204 . H2042 . 1.018(2) no C205 . C206 . 1.524(3) yes C205 . C209 . 1.539(2) yes C205 . H2051 . 0.974(2) no C206 . C207 . 1.523(3) yes C206 . H2061 . 1.066(2) no C206 . H2062 . 1.006(2) no C207 . C208 . 1.530(2) yes C207 . C210 . 1.520(3) yes C207 . H2071 . 0.958(2) no C208 . H2081 . 0.998(2) no C208 . H2082 . 0.979(2) no C209 . H2091 . 1.023(2) no C209 . H2092 . 1.074(2) no C210 . H2101 . 0.975(2) no C210 . H2102 . 0.978(2) 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 . S1 . C5 . 93.76(7) yes C3 . O1 . C6 . 118.8(1) no C10 . O11 . H11 . 106.21(9) no S1 . C2 . C3 . 107.97(9) yes S1 . C2 . C10 . 122.23(9) yes C3 . C2 . C10 . 129.8(1) yes O1 . C3 . C2 . 121.3(1) yes O1 . C3 . C4 . 124.1(1) yes C2 . C3 . C4 . 114.6(1) yes C3 . C4 . C5 . 111.8(1) yes C3 . C4 . H41 . 122.2(2) no C5 . C4 . H41 . 125.9(1) no S1 . C5 . C4 . 111.9(1) yes S1 . C5 . H51 . 119.4(1) no C4 . C5 . H51 . 128.7(2) no O1 . C6 . H61 . 104.4(1) no O1 . C6 . H62 . 110.1(2) no H61 . C6 . H62 . 118.6(2) no O1 . C6 . H63 . 112.0(2) no H61 . C6 . H63 . 110.6(2) no H62 . C6 . H63 . 101.4(2) no O11 . C10 . C2 . 108.21(9) no O11 . C10 . C101 . 102.88(9) no C2 . C10 . C101 . 109.5(1) yes O11 . C10 . C201 . 105.1(1) yes C2 . C10 . C201 . 109.5(1) no C101 . C10 . C201 . 120.7(1) yes C10 . C101 . C102 . 111.8(1) no C10 . C101 . C108 . 115.8(1) no C102 . C101 . C108 . 106.5(1) no C10 . C101 . C109 . 107.5(1) no C102 . C101 . C109 . 106.2(1) no C108 . C101 . C109 . 108.5(1) no C101 . C102 . C103 . 111.5(1) no C101 . C102 . H1021 . 108.3(1) no C103 . C102 . H1021 . 110.3(1) no C101 . C102 . H1022 . 112.7(1) no C103 . C102 . H1022 . 103.6(1) no H1021 . C102 . H1022 . 110.4(1) no C102 . C103 . C104 . 110.0(1) no C102 . C103 . C110 . 110.0(1) no C104 . C103 . C110 . 109.6(1) no C102 . C103 . H1031 . 108.0(1) no C104 . C103 . H1031 . 109.2(2) no C110 . C103 . H1031 . 110.1(2) no C103 . C104 . C105 . 108.6(1) no C103 . C104 . H1041 . 109.9(2) no C105 . C104 . H1041 . 111.3(2) no C103 . C104 . H1042 . 109.4(2) no C105 . C104 . H1042 . 110.6(2) no H1041 . C104 . H1042 . 107.0(1) no C104 . C105 . C106 . 110.0(1) no C104 . C105 . C109 . 109.9(1) no C106 . C105 . C109 . 109.0(1) no C104 . C105 . H1051 . 110.8(1) no C106 . C105 . H1051 . 109.6(2) no C109 . C105 . H1051 . 107.4(1) no C105 . C106 . C107 . 109.2(1) no C105 . C106 . H1061 . 110.3(2) no C107 . C106 . H1061 . 109.2(2) no C105 . C106 . H1062 . 112.3(2) no C107 . C106 . H1062 . 106.5(2) no H1061 . C106 . H1062 . 109.2(2) no C106 . C107 . C108 . 110.5(1) no C106 . C107 . C110 . 109.7(1) no C108 . C107 . C110 . 109.3(1) no C106 . C107 . H1071 . 113.7(1) no C108 . C107 . H1071 . 108.5(1) no C110 . C107 . H1071 . 105.0(1) no C101 . C108 . C107 . 111.3(1) no C101 . C108 . H1081 . 113.5(1) no C107 . C108 . H1081 . 109.5(1) no C101 . C108 . H1082 . 110.9(1) no C107 . C108 . H1082 . 106.7(1) no H1081 . C108 . H1082 . 104.5(1) no C101 . C109 . C105 . 111.9(1) no C101 . C109 . H1091 . 109.0(1) no C105 . C109 . H1091 . 113.1(1) no C101 . C109 . H1092 . 110.9(1) no C105 . C109 . H1092 . 107.1(1) no H1091 . C109 . H1092 . 104.6(1) no C103 . C110 . C107 . 108.5(1) no C103 . C110 . H1101 . 113.2(2) no C107 . C110 . H1101 . 111.5(2) no C103 . C110 . H1102 . 115.2(2) no C107 . C110 . H1102 . 108.1(2) no H1101 . C110 . H1102 . 100.1(1) no C10 . C201 . C202 . 111.7(1) no C10 . C201 . C208 . 107.5(1) no C202 . C201 . C208 . 107.0(1) no C10 . C201 . C209 . 116.4(1) no C202 . C201 . C209 . 107.4(1) no C208 . C201 . C209 . 106.3(1) no C201 . C202 . C203 . 112.0(1) no C201 . C202 . H2021 . 109.8(1) no C203 . C202 . H2021 . 105.9(1) no C201 . C202 . H2022 . 106.9(1) no C203 . C202 . H2022 . 110.4(1) no H2021 . C202 . H2022 . 112.0(1) no C202 . C203 . C204 . 108.6(1) no C202 . C203 . C210 . 110.8(1) no C204 . C203 . C210 . 109.6(2) no C202 . C203 . H2031 . 109.0(2) no C204 . C203 . H2031 . 110.9(2) no C210 . C203 . H2031 . 108.0(2) no C203 . C204 . C205 . 109.2(1) no C203 . C204 . H2041 . 107.1(2) no C205 . C204 . H2041 . 114.9(2) no C203 . C204 . H2042 . 106.9(2) no C205 . C204 . H2042 . 114.7(2) no H2041 . C204 . H2042 . 103.6(1) no C204 . C205 . C206 . 109.5(1) no C204 . C205 . C209 . 110.8(1) no C206 . C205 . C209 . 109.4(1) no C204 . C205 . H2051 . 107.3(2) no C206 . C205 . H2051 . 109.0(2) no C209 . C205 . H2051 . 110.9(2) no C205 . C206 . C207 . 108.6(1) no C205 . C206 . H2061 . 107.3(2) no C207 . C206 . H2061 . 111.6(2) no C205 . C206 . H2062 . 106.8(2) no C207 . C206 . H2062 . 108.4(2) no H2061 . C206 . H2062 . 113.9(2) no C206 . C207 . C208 . 109.6(1) no C206 . C207 . C210 . 110.1(1) no C208 . C207 . C210 . 109.3(1) no C206 . C207 . H2071 . 110.9(2) no C208 . C207 . H2071 . 105.5(1) no C210 . C207 . H2071 . 111.4(2) no C201 . C208 . C207 . 112.4(1) no C201 . C208 . H2081 . 110.0(1) no C207 . C208 . H2081 . 111.1(1) no C201 . C208 . H2082 . 108.2(1) no C207 . C208 . H2082 . 112.7(1) no H2081 . C208 . H2082 . 102.0(1) no C201 . C209 . C205 . 111.0(1) no C201 . C209 . H2091 . 109.4(1) no C205 . C209 . H2091 . 103.6(1) no C201 . C209 . H2092 . 108.1(1) no C205 . C209 . H2092 . 110.5(1) no H2091 . C209 . H2092 . 114.2(1) no C203 . C210 . C207 . 108.6(1) no C203 . C210 . H2101 . 107.3(2) no C207 . C210 . H2101 . 111.6(2) no C203 . C210 . H2102 . 109.9(2) no C207 . C210 . H2102 . 110.9(2) no H2101 . C210 . H2102 . 108.4(2) no