Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_General _audit_creation_date 'Sun Aug 26 00:03:18 2001' _audit_creation_method 'by teXsan' _audit_update_record ? _journal_coden_Cambridge 207 loop_ _publ_author_name 'Hara, Kenji' 'Itoh, Nobuhiro' 'Iyoda, Masahiko' 'Matsumoto, Aoi' 'Matsuyamma, Haruo' 'Ohira, Nahoko' 'Yoshida, Matsato' #--------------------------------------------------------------------------- #-- # PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_coeditor_code ? #--------------------------------------------------------------------------- #-- # SUBMISSION DETAILS _publ_contact_author_name 'Prof Masahiko Iyoda' _publ_contact_author_address ; Department of Chemistry Graduate School of Science, Tokyo Metropolitan University Hachioji Tokyo 192-0397 JAPAN ; _publ_contact_author_email 'iyoda-masahiko@c.metro-u.ac.jp' _publ_contact_author_fax '+81-426-77-2525' _publ_contact_author_phone '+81-426-77-2547' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_journal 'J. Chem. Soc., Perkin Trans. 1' _publ_requested_category ' CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? #--------------------------------------------------------------------------- #-- # TITLE AND AUTHOR LIST _publ_section_title ; Conjugate Addition of 6-Membered Hydrazine, to Chiral t-Butyl (E)-2-(p-Tolylsulfinyl)cinnamates. Synthesis of (S)-Celacinnine ; #--------------------------------------------------------------------------- #-- # TEXT _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_comment ; ENTER TEXT ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation, Rigaku Corporation. (1999). teXsan. Single Crystal Structure Analysis Software. Version 1.10. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _publ_section_exptl_prep ; ENTER COMPOUND PREPARATION DETAILS ; _publ_section_exptl_refinement ; ENTER SPECIAL DETAILS OF THE REFINEMENT ; #--------------------------------------------------------------------------- #-- data_A_TEXRAY.INF_file_is_not_p _database_code_CSD 170583 #--------------------------------------------------------------------------- #-- # CHEMICAL DATA _chemical_formula_sum 'C13 H18 N2 O ' _chemical_formula_moiety 'C13 H18 N2 O ' _chemical_formula_weight 218.30 _chemical_melting_point 90.1-91.0 #--------------------------------------------------------------------------- #-- # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,-z _cell_length_a 6.794(5) _cell_length_b 8.125(6) _cell_length_c 11.675(4) _cell_angle_alpha 90 _cell_angle_beta 103.60(4) _cell_angle_gamma 90 _cell_volume 626.4(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 14.7 _cell_measurement_theta_max 15.0 _cell_measurement_temperature 296.2 #--------------------------------------------------------------------------- #-- _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.660 _exptl_crystal_size_mid 0.440 _exptl_crystal_size_min 0.400 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.157 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.920 _exptl_absorpt_correction_T_max 0.998 #--------------------------------------------------------------------------- #-- # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 1671 _diffrn_reflns_av_R_equivalents 0.019 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 0.9980 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.9980 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.07 #--------------------------------------------------------------------------- #-- # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 3.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 3.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1543 _reflns_number_gt 957 _reflns_threshold_expression F^2^>3.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.0646 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 957 _refine_ls_number_parameters 147 _refine_ls_goodness_of_fit_ref 1.246 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00172|Fo|^2^]' _refine_ls_shift/su_max 0.0023 _refine_diff_density_max 0.29 _refine_diff_density_min -0.22 _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.43(4) _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack 1.6(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'N' 'N' 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #--------------------------------------------------------------------------- #-- # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 1.0072(3) 0.695(1) 0.8273(2) 0.0712(8) Uani 1.00 d . . . N(1) N 0.7930(4) 0.620(1) 0.9390(3) 0.0575(7) Uani 1.00 d . . . N(2) N 0.4255(3) 0.734(1) 0.7940(2) 0.0474(7) Uani 1.00 d . . . C(1) C 0.5185(4) 0.697(1) 0.6966(3) 0.0460(7) Uani 1.00 d . . . C(2) C 0.6910(5) 0.569(1) 0.7323(3) 0.0556(9) Uani 1.00 d . . . C(3) C 0.8484(4) 0.632(1) 0.8368(3) 0.0528(8) Uani 1.00 d . . . C(4) C 0.8634(6) 0.735(1) 1.0339(3) 0.070(1) Uani 1.00 d . . . C(5) C 0.7073(6) 0.868(2) 1.0308(4) 0.074(1) Uani 1.00 d . . . C(6) C 0.6433(5) 0.957(1) 0.9131(4) 0.065(1) Uani 1.00 d . . . C(7) C 0.4381(5) 0.906(1) 0.8329(4) 0.0629(10) Uani 1.00 d . . . C(8) C 0.3671(4) 0.634(1) 0.5876(3) 0.0462(7) Uani 1.00 d . . . C(9) C 0.3692(5) 0.694(1) 0.4771(3) 0.0566(9) Uani 1.00 d . . . C(10) C 0.2376(7) 0.633(1) 0.3777(3) 0.071(1) Uani 1.00 d . . . C(11) C 0.1027(6) 0.512(2) 0.3870(4) 0.073(1) Uani 1.00 d . . . C(12) C 0.0958(6) 0.453(1) 0.4957(4) 0.076(1) Uani 1.00 d . . . C(13) C 0.2282(6) 0.513(1) 0.5958(3) 0.063(1) Uani 1.00 d . . . H(1) H 0.5762 0.8038 0.6754 0.0547 Uiso 1.00 calc . . . H(2) H 0.6370 0.4769 0.7536 0.0674 Uiso 1.00 calc . . . H(3) H 0.7522 0.5589 0.6686 0.0674 Uiso 1.00 calc . . . H(4) H 0.7060 0.5415 0.9498 0.0706 Uiso 1.00 calc . . . H(5) H 0.8867 0.6877 1.1074 0.0845 Uiso 1.00 calc . . . H(6) H 0.9871 0.7927 1.0258 0.0845 Uiso 1.00 calc . . . H(7) H 0.5908 0.8275 1.0480 0.0910 Uiso 1.00 calc . . . H(8) H 0.7616 0.9560 1.0891 0.0910 Uiso 1.00 calc . . . H(9) H 0.7435 0.9447 0.8703 0.0784 Uiso 1.00 calc . . . H(10) H 0.6363 1.0787 0.9284 0.0784 Uiso 1.00 calc . . . H(11) H 0.4117 0.9818 0.7663 0.0760 Uiso 1.00 calc . . . H(12) H 0.3371 0.9303 0.8768 0.0760 Uiso 1.00 calc . . . H(13) H 0.3620 0.6600 0.8309 0.0580 Uiso 1.00 calc . . . H(14) H 0.4645 0.7845 0.4700 0.0690 Uiso 1.00 calc . . . H(15) H 0.2400 0.6839 0.3021 0.0864 Uiso 1.00 calc . . . H(16) H 0.0127 0.4771 0.3179 0.0888 Uiso 1.00 calc . . . H(17) H 0.0006 0.3783 0.5020 0.0932 Uiso 1.00 calc . . . H(18) H 0.2244 0.4784 0.6712 0.0782 Uiso 1.00 calc . . . 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 O(1) 0.0314(10) 0.101(2) 0.082(2) 0.001(1) 0.0155(10) 0.003(2) N(1) 0.049(1) 0.059(2) 0.062(1) -0.008(1) 0.008(1) 0.011(1) N(2) 0.034(1) 0.055(1) 0.056(1) -0.005(1) 0.016(1) -0.010(1) C(1) 0.034(1) 0.054(2) 0.051(1) -0.008(1) 0.0115(9) -0.005(1) C(2) 0.043(2) 0.059(2) 0.067(2) 0.004(1) 0.016(1) -0.013(2) C(3) 0.035(1) 0.059(2) 0.063(1) 0.011(1) 0.009(1) 0.006(2) C(4) 0.057(2) 0.095(3) 0.053(2) -0.021(2) 0.004(2) -0.005(2) C(5) 0.057(2) 0.099(3) 0.069(2) -0.026(2) 0.019(2) -0.035(2) C(6) 0.050(2) 0.059(2) 0.086(2) -0.008(2) 0.016(2) -0.029(2) C(7) 0.045(2) 0.061(2) 0.085(2) 0.004(2) 0.018(2) -0.027(2) C(8) 0.037(1) 0.052(2) 0.050(1) 0.002(1) 0.010(1) -0.008(1) C(9) 0.063(2) 0.052(2) 0.055(1) -0.003(2) 0.016(1) 0.000(2) C(10) 0.080(2) 0.076(3) 0.051(2) 0.002(2) 0.003(1) -0.005(2) C(11) 0.056(2) 0.089(3) 0.065(2) -0.001(2) -0.006(2) -0.027(2) C(12) 0.058(2) 0.091(4) 0.077(2) -0.034(2) 0.015(2) -0.022(2) C(13) 0.056(2) 0.073(3) 0.064(2) -0.027(2) 0.019(1) -0.006(2) #--------------------------------------------------------------------------- #-- _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution SIR88 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' _computing_molecular_graphics ? #--------------------------------------------------------------------------- #-- _geom_special_details ; ? ; 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 O(1) C(3) 1.226(4) . . yes N(1) C(3) 1.339(4) . . yes N(1) C(4) 1.447(5) . . yes N(1) H(4) 0.81(4) . . no N(2) C(1) 1.465(4) . . yes N(2) C(7) 1.459(5) . . yes N(2) H(13) 0.82(3) . . no C(1) C(2) 1.549(4) . . yes C(1) C(8) 1.522(4) . . yes C(1) H(1) 0.99(3) . . no C(2) C(3) 1.503(4) . . yes C(2) H(2) 0.90(3) . . no C(2) H(3) 0.93(4) . . no C(4) C(5) 1.509(6) . . yes C(4) H(5) 0.99(4) . . no C(4) H(6) 0.91(3) . . no C(5) C(6) 1.518(6) . . yes C(5) H(7) 0.96(4) . . no C(5) H(8) 1.00(5) . . no C(6) C(7) 1.531(5) . . yes C(6) H(9) 1.04(3) . . no C(6) H(10) 0.91(5) . . no C(7) H(11) 0.98(3) . . no C(7) H(12) 0.95(4) . . no C(8) C(9) 1.372(4) . . yes C(8) C(13) 1.384(5) . . yes C(9) C(10) 1.389(5) . . yes C(9) H(14) 0.93(4) . . no C(10) C(11) 1.367(6) . . yes C(10) H(15) 0.97(4) . . no C(11) C(12) 1.365(6) . . yes C(11) H(16) 0.951 . . no C(12) C(13) 1.393(5) . . yes C(12) H(17) 0.96(7) . . no C(13) H(18) 1.01(4) . . 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 C(3) N(1) C(4) 121.9(3) . 1_555 1_555 yes C(3) N(1) H(4) 112(2) . 1_555 1_555 no C(4) N(1) H(4) 113(2) . 1_555 1_555 no C(1) N(2) C(7) 116.2(3) . 1_555 1_555 yes C(1) N(2) H(13) 111(2) . 1_555 1_555 no C(7) N(2) H(13) 103(2) . 1_555 1_555 no N(2) C(1) C(2) 111.1(3) . 1_555 1_555 yes N(2) C(1) C(8) 113.2(2) . 1_555 1_555 yes N(2) C(1) H(1) 109(1) . 1_555 1_555 no C(2) C(1) C(8) 109.1(2) . 1_555 1_555 yes C(2) C(1) H(1) 107(1) . 1_555 1_555 no C(8) C(1) H(1) 106(1) . 1_555 1_555 no C(1) C(2) C(3) 110.1(3) . 1_555 1_555 yes C(1) C(2) H(2) 106(2) . 1_555 1_555 no C(1) C(2) H(3) 106(2) . 1_555 1_555 no C(3) C(2) H(2) 108(2) . 1_555 1_555 no C(3) C(2) H(3) 114(2) . 1_555 1_555 no H(2) C(2) H(3) 111(3) . 1_555 1_555 no O(1) C(3) N(1) 123.1(3) . 1_555 1_555 yes O(1) C(3) C(2) 123.1(3) . 1_555 1_555 yes N(1) C(3) C(2) 113.7(3) . 1_555 1_555 yes N(1) C(4) C(5) 109.8(3) . 1_555 1_555 yes N(1) C(4) H(5) 109(2) . 1_555 1_555 no N(1) C(4) H(6) 111(2) . 1_555 1_555 no C(5) C(4) H(5) 111(2) . 1_555 1_555 no C(5) C(4) H(6) 107(2) . 1_555 1_555 no H(5) C(4) H(6) 107(3) . 1_555 1_555 no C(4) C(5) C(6) 114.4(3) . 1_555 1_555 yes C(4) C(5) H(7) 111(2) . 1_555 1_555 no C(4) C(5) H(8) 108(2) . 1_555 1_555 no C(6) C(5) H(7) 111(2) . 1_555 1_555 no C(6) C(5) H(8) 112(2) . 1_555 1_555 no H(7) C(5) H(8) 96(3) . 1_555 1_555 no C(5) C(6) C(7) 116.5(4) . 1_555 1_555 yes C(5) C(6) H(9) 113(1) . 1_555 1_555 no C(5) C(6) H(10) 106(2) . 1_555 1_555 no C(7) C(6) H(9) 106(1) . 1_555 1_555 no C(7) C(6) H(10) 104(2) . 1_555 1_555 no H(9) C(6) H(10) 108(3) . 1_555 1_555 no N(2) C(7) C(6) 115.0(3) . 1_555 1_555 yes N(2) C(7) H(11) 109(2) . 1_555 1_555 no N(2) C(7) H(12) 110(2) . 1_555 1_555 no C(6) C(7) H(11) 104(1) . 1_555 1_555 no C(6) C(7) H(12) 106(2) . 1_555 1_555 no H(11) C(7) H(12) 110(3) . 1_555 1_555 no C(1) C(8) C(9) 120.7(3) . 1_555 1_555 yes C(1) C(8) C(13) 120.9(3) . 1_555 1_555 yes C(9) C(8) C(13) 118.4(3) . 1_555 1_555 yes C(8) C(9) C(10) 121.0(4) . 1_555 1_555 yes C(8) C(9) H(14) 122(2) . 1_555 1_555 no C(10) C(9) H(14) 116(2) . 1_555 1_555 no C(9) C(10) C(11) 120.3(4) . 1_555 1_555 yes C(9) C(10) H(15) 121(2) . 1_555 1_555 no C(11) C(10) H(15) 117(2) . 1_555 1_555 no C(10) C(11) C(12) 119.5(3) . 1_555 1_555 yes C(10) C(11) H(16) 118.3 . 1_555 1_555 no C(12) C(11) H(16) 122.1 . 1_555 1_555 no C(11) C(12) C(13) 120.6(4) . 1_555 1_555 yes C(11) C(12) H(17) 113(3) . 1_555 1_555 no C(13) C(12) H(17) 125(3) . 1_555 1_555 no C(8) C(13) C(12) 120.3(3) . 1_555 1_555 yes C(8) C(13) H(18) 121(2) . 1_555 1_555 no C(12) C(13) H(18) 118(2) . 1_555 1_555 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 O(1) C(3) N(1) C(4) 26.3(5) 1_555 1_555 1_555 1_555 yes O(1) C(3) C(2) C(1) -99.1(4) 1_555 1_555 1_555 1_555 yes N(1) C(3) C(2) C(1) 76.8(4) 1_555 1_555 1_555 1_555 yes N(1) C(4) C(5) C(6) -54.2(4) 1_555 1_555 1_555 1_555 yes N(2) C(1) C(2) C(3) -57.4(4) 1_555 1_555 1_555 1_555 yes N(2) C(1) C(8) C(9) 135.5(3) 1_555 1_555 1_555 1_555 yes N(2) C(1) C(8) C(13) -47.3(4) 1_555 1_555 1_555 1_555 yes N(2) C(7) C(6) C(5) -63.1(5) 1_555 1_555 1_555 1_555 yes C(1) N(2) C(7) C(6) -79.1(4) 1_555 1_555 1_555 1_555 yes C(1) C(8) C(9) C(10) 177.6(3) 1_555 1_555 1_555 1_555 yes C(1) C(8) C(13) C(12) -177.6(3) 1_555 1_555 1_555 1_555 yes C(2) C(1) N(2) C(7) 119.2(3) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(8) C(9) -100.3(4) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(8) C(13) 76.9(4) 1_555 1_555 1_555 1_555 yes C(2) C(3) N(1) C(4) -149.5(3) 1_555 1_555 1_555 1_555 yes C(3) N(1) C(4) C(5) 96.4(4) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(1) C(8) 177.1(3) 1_555 1_555 1_555 1_555 yes C(4) C(5) C(6) C(7) 102.3(4) 1_555 1_555 1_555 1_555 yes C(7) N(2) C(1) C(8) -117.6(3) 1_555 1_555 1_555 1_555 yes C(8) C(9) C(10) C(11) -0.8(6) 1_555 1_555 1_555 1_555 yes C(8) C(13) C(12) C(11) 0.7(6) 1_555 1_555 1_555 1_555 yes C(9) C(8) C(13) C(12) -0.3(5) 1_555 1_555 1_555 1_555 yes C(9) C(10) C(11) C(12) 1.2(6) 1_555 1_555 1_555 1_555 yes C(10) C(9) C(8) C(13) 0.4(5) 1_555 1_555 1_555 1_555 yes C(10) C(11) C(12) C(13) -1.2(6) 1_555 1_555 1_555 1_555 yes #--------------------------------------------------------------------------- #-- 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 O(1) H(8) 2.61(5) . 2_747 ? O(1) H(11) 2.87(3) . 1_655 ? O(1) N(2) 2.977(4) . 1_655 ? O(1) H(18) 3.19(4) . 1_655 ? O(1) C(7) 3.369(5) . 1_655 ? O(1) H(10) 3.48(4) . 2_747 ? O(1) C(5) 3.484(5) . 2_747 ? O(1) C(11) 3.528(5) . 2_656 ? N(1) H(11) 2.94(4) . 2_647 ? N(1) H(6) 3.10(4) . 2_747 ? N(1) H(8) 3.47(4) . 2_747 ? N(1) H(7) 3.54(4) . 2_647 ? N(1) H(10) 3.58(4) . 2_647 ? N(2) H(8) 3.06(5) . 2_647 ? C(2) H(15) 3.28(5) . 2_646 ? C(2) H(14) 3.38(4) . 2_646 ? C(3) H(8) 3.01(5) . 2_747 ? C(3) H(6) 3.30(4) . 2_747 ? C(3) H(13) 3.39(3) . 1_655 ? C(4) H(11) 3.16(4) . 2_647 ? C(4) H(9) 3.52(3) . 2_747 ? C(4) H(15) 3.54(4) . 1_656 ? C(5) H(4) 3.31(4) . 2_657 ? C(5) H(18) 3.45(4) . 2_657 ? C(5) H(10) 3.46(4) . 2_647 ? C(6) H(15) 3.30(4) . 2_656 ? C(6) H(4) 3.35(4) . 2_657 ? C(6) H(7) 3.48(5) . 2_657 ? C(7) H(5) 3.33(4) . 2_657 ? C(7) H(4) 3.41(3) . 2_657 ? C(8) H(17) 3.09(7) . 2_556 ? C(8) H(14) 3.30(5) . 2_646 ? C(9) H(17) 2.98(7) . 2_556 ? C(9) H(2) 3.45(4) . 2_656 ? C(9) H(3) 3.45(4) . 2_656 ? C(10) H(17) 3.10(6) . 2_556 ? C(10) H(1) 3.11(3) . 2_646 ? C(10) H(9) 3.18(3) . 2_646 ? C(10) H(3) 3.32(4) . 2_656 ? C(10) H(5) 3.44(4) . 1_454 ? C(10) H(12) 3.48(4) . 2_646 ? C(10) H(2) 3.53(4) . 2_656 ? C(11) H(1) 2.98(3) . 2_646 ? C(11) H(9) 3.32(3) . 2_646 ? C(11) H(17) 3.33(6) . 2_556 ? C(11) H(5) 3.47(4) . 1_454 ? C(11) H(12) 3.55(4) . 2_546 ? C(12) H(14) 3.26(4) . 2_646 ? C(12) H(17) 3.41(6) . 2_556 ? C(12) H(1) 3.51(3) . 2_646 ? C(12) H(2) 3.58(4) . 1_455 ? C(13) H(14) 3.08(4) . 2_646 ? C(13) H(17) 3.30(7) . 2_556 ? C(13) H(2) 3.59(4) . 1_455 ? H(1) H(15) 3.29(6) . 2_656 ? H(2) H(14) 3.06(5) . 2_646 ? H(2) H(15) 3.16(6) . 2_646 ? H(2) H(18) 3.31(5) . 1_655 ? H(2) H(17) 3.41(7) . 1_655 ? H(3) H(15) 2.67(6) . 2_646 ? H(3) H(14) 2.93(5) . 2_646 ? H(3) H(7) 3.24(6) . 2_647 ? H(3) H(8) 3.55(5) . 2_647 ? H(3) H(6) 3.59(5) . 2_747 ? H(4) H(11) 2.63(5) . 2_647 ? H(4) H(7) 2.87(6) . 2_647 ? H(4) H(10) 2.93(5) . 2_647 ? H(4) H(8) 3.13(5) . 2_647 ? H(4) H(6) 3.40(6) . 2_747 ? H(5) H(11) 2.62(6) . 2_647 ? H(5) H(15) 2.81(6) . 1_656 ? H(5) H(9) 3.02(5) . 2_747 ? H(5) H(12) 3.22(6) . 2_647 ? H(5) H(10) 3.52(5) . 2_747 ? H(5) H(10) 3.57(5) . 2_647 ? H(6) H(10) 3.16(5) . 2_747 ? H(6) H(15) 3.37(6) . 1_656 ? H(6) H(9) 3.39(5) . 2_747 ? H(6) H(11) 3.47(5) . 1_655 ? H(7) H(10) 2.64(7) . 2_647 ? H(7) H(18) 3.28(6) . 2_657 ? H(7) H(11) 3.38(6) . 2_647 ? H(7) H(12) 3.51(6) . 2_647 ? H(8) H(18) 2.64(6) . 2_657 ? H(8) H(13) 2.72(6) . 2_657 ? H(9) H(15) 2.64(5) . 2_656 ? H(10) H(15) 3.15(6) . 2_656 ? H(10) H(13) 3.57(5) . 2_657 ? H(12) H(15) 3.13(5) . 2_656 ? H(13) H(17) 3.56(7) . 2_556 ? H(14) H(18) 3.36(6) . 2_656 ? H(14) H(17) 3.45(7) . 2_556 ? H(14) H(17) 3.59(7) . 2_656 ? H(15) H(17) 3.57(7) . 2_556 ? #--------------------------------------------------------------------------- #--