# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 # CCDC Number: 207/505 data_General _audit_creation_date 'Wed Mar 15 10:17:14 2000' _audit_creation_method 'by teXsan' _audit_update_record ? #------------------------------------------------------------------------------ # 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 ' ENTER NAME' _publ_contact_author_address ; ENTER ADDRESS ; _publ_contact_author_email ' ENTER EMAIL ADDRESS ' _publ_contact_author_fax ' ENTER FAX NUMBER ' _publ_contact_author_phone ' ENTER PHONE NUMBER ' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_journal ' ENTER JOURNAL NAME HERE' _publ_requested_category ' CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? #------------------------------------------------------------------------------ # TITLE AND AUTHOR LIST _publ_section_title ; ENTER SECTION TITLE ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; loop_ _publ_author_name _publ_author_footnote _publ_author_address ' FIRST AUTHORS NAME ' ; FIRST AUTHORS FOOTNOTES ; ; FIRST AUTHORS ADDRESS ; _publ_section_synopsis ; ENTER SYNOPSIS ; #------------------------------------------------------------------------------ # 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. 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_20000117b #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C11 H12 Cl N O4 ' _chemical_formula_moiety 'C11 H12 Cl N O4 ' _chemical_formula_weight 257.67 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z _cell_length_a 10.615(1) _cell_length_b 14.277(1) _cell_length_c 7.838(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1187.8(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 24 _cell_measurement_theta_min 12.7 _cell_measurement_theta_max 14.7 _cell_measurement_temperature 297.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'column' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.280 _exptl_crystal_size_min 0.180 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.323 _exptl_absorpt_correction_type ? _exptl_absorpt_process_details psi-scan _exptl_absorpt_correction_T_min 0.894 _exptl_absorpt_correction_T_max 0.939 #------------------------------------------------------------------------------ # 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 1601 _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_theta_max 27.49 _diffrn_measured_fraction_theta_max 1.0000 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.0000 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 1.01 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -10.0 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^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1582 _reflns_number_gt 1108 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0515 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 1582 _refine_ls_number_parameters 203 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00046|Fo|^2^]' _refine_ls_shift/su_max 0.0016 _refine_diff_density_max 0.15 _refine_diff_density_min -0.16 _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.003(5) _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? 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) ; 'Cl' 'Cl' 0.148 0.159 ;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) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'N' 'N' 0.006 0.003 ;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 Cl(1) Cl 0.10171(9) -0.16232(8) -0.5180(1) 0.0671(3) Uani 1.00 d . . . O(1) O -0.2486(4) -0.4903(2) -1.1906(4) 0.0700(8) Uani 1.00 d . . . O(2) O -0.0876(3) -0.4413(2) -1.3316(4) 0.0782(10) Uani 1.00 d . . . O(3) O -0.2829(2) -0.0779(2) -0.7318(3) 0.0580(8) Uani 1.00 d . . . O(4) O -0.0614(3) 0.0292(2) -0.5050(4) 0.0694(8) Uani 1.00 d . . . N(1) N -0.1697(3) -0.4315(2) -1.2239(4) 0.0540(9) Uani 1.00 d . . . C(1) C -0.1741(3) -0.3420(2) -1.1285(4) 0.0435(8) Uani 1.00 d . . . C(2) C -0.1017(3) -0.2679(3) -1.1840(4) 0.0489(8) Uani 1.00 d . . . C(3) C -0.1075(4) -0.1852(2) -1.0948(4) 0.0485(9) Uani 1.00 d . . . C(4) C -0.1822(3) -0.1765(2) -0.9493(4) 0.0409(7) Uani 1.00 d . . . C(5) C -0.2537(3) -0.2530(3) -0.8978(4) 0.0468(9) Uani 1.00 d . . . C(6) C -0.2509(3) -0.3360(2) -0.9873(4) 0.0478(8) Uani 1.00 d . . . C(7) C -0.1816(3) -0.0857(2) -0.8485(4) 0.0448(8) Uani 1.00 d . . . C(8) C -0.0601(3) -0.0760(2) -0.7404(4) 0.0402(8) Uani 1.00 d . . . C(9) C -0.0529(4) -0.1527(3) -0.6077(5) 0.0544(10) Uani 1.00 d . . . C(10) C -0.0564(3) 0.0207(2) -0.6586(5) 0.0489(9) Uani 1.00 d . . . C(11) C -0.0457(6) 0.1041(3) -0.7726(8) 0.079(2) Uani 1.00 d . . . H(1) H -0.047(4) -0.279(3) -1.279(5) 0.069(10) Uiso 1.00 calc . . . H(2) H -0.063(4) -0.139(3) -1.129(4) 0.052(9) Uiso 1.00 calc . . . H(3) H -0.302(3) -0.245(3) -0.798(5) 0.053(9) Uiso 1.00 calc . . . H(4) H -0.298(3) -0.386(2) -0.949(4) 0.050(9) Uiso 1.00 calc . . . H(5) H -0.182(3) -0.034(2) -0.927(4) 0.034(7) Uiso 1.00 calc . . . H(6) H -0.350(5) -0.072(4) -0.787(7) 0.104(9) Uiso 1.00 calc . . . H(7) H 0.010(4) -0.081(3) -0.816(5) 0.055(10) Uiso 1.00 calc . . . H(8) H -0.072(4) -0.214(3) -0.658(5) 0.055(9) Uiso 1.00 calc . . . H(9) H -0.108(3) -0.132(2) -0.514(5) 0.052(9) Uiso 1.00 calc . . . H(10) H -0.108(5) 0.101(4) -0.853(7) 0.102(9) Uiso 1.00 calc . . . H(11) H 0.031(8) 0.109(5) -0.826(9) 0.163(6) Uiso 1.00 calc . . . H(12) H -0.065(7) 0.151(5) -0.708(9) 0.161(7) 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 Cl(1) 0.0550(5) 0.0880(7) 0.0583(5) -0.0016(5) -0.0149(4) 0.0222(5) O(1) 0.081(2) 0.049(1) 0.080(2) -0.012(1) -0.005(2) -0.005(1) O(2) 0.086(2) 0.085(2) 0.063(2) 0.001(2) 0.008(2) -0.026(2) O(3) 0.043(1) 0.080(2) 0.051(1) 0.010(1) 0.000(1) -0.012(1) O(4) 0.069(2) 0.084(2) 0.055(2) 0.004(1) 0.004(1) -0.025(2) N(1) 0.060(2) 0.055(2) 0.047(2) 0.001(2) -0.013(2) -0.003(1) C(1) 0.046(2) 0.046(2) 0.039(1) -0.003(1) -0.008(1) 0.001(1) C(2) 0.048(2) 0.062(2) 0.036(1) -0.008(2) 0.003(2) 0.000(1) C(3) 0.053(2) 0.051(2) 0.042(2) -0.014(2) 0.001(2) 0.007(1) C(4) 0.038(1) 0.051(2) 0.034(1) -0.001(1) -0.004(1) 0.004(1) C(5) 0.044(2) 0.060(2) 0.037(1) -0.007(2) 0.000(1) 0.002(1) C(6) 0.049(2) 0.050(2) 0.045(2) -0.011(2) 0.001(2) 0.007(2) C(7) 0.047(2) 0.047(2) 0.041(2) -0.001(1) -0.003(1) 0.003(1) C(8) 0.040(2) 0.045(2) 0.036(1) -0.001(1) -0.001(1) 0.001(1) C(9) 0.053(2) 0.057(2) 0.053(2) -0.007(2) -0.014(2) 0.007(2) C(10) 0.039(2) 0.051(2) 0.056(2) 0.003(1) 0.002(2) -0.008(2) C(11) 0.101(4) 0.047(2) 0.087(4) -0.005(3) -0.004(3) -0.001(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 SIR92 _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 Cl(1) C(9) 1.791(4) . . yes O(1) N(1) 1.215(4) . . yes O(2) N(1) 1.221(4) . . yes O(3) C(7) 1.417(4) . . yes O(3) H(6) 0.84(5) . . no O(4) C(10) 1.211(4) . . yes N(1) C(1) 1.480(4) . . yes C(1) C(2) 1.378(4) . . yes C(1) C(6) 1.377(4) . . yes C(2) C(3) 1.373(5) . . yes C(2) H(1) 0.96(4) . . no C(3) C(4) 1.395(4) . . yes C(3) H(2) 0.86(4) . . no C(4) C(5) 1.390(4) . . yes C(4) C(7) 1.519(4) . . yes C(5) C(6) 1.377(5) . . yes C(5) H(3) 0.95(4) . . no C(6) H(4) 0.93(3) . . no C(7) C(8) 1.549(4) . . yes C(7) H(5) 0.96(3) . . no C(8) C(9) 1.513(5) . . yes C(8) C(10) 1.522(5) . . yes C(8) H(7) 0.95(4) . . no C(9) H(8) 0.98(4) . . no C(9) H(9) 0.98(4) . . no C(10) C(11) 1.493(6) . . yes C(11) H(10) 0.92(5) . . no C(11) H(11) 0.92(8) . . no C(11) H(12) 0.87(7) . . 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(7) O(3) H(6) 108(3) . 1_555 1_555 no O(1) N(1) O(2) 124.1(3) . 1_555 1_555 yes O(1) N(1) C(1) 117.8(3) . 1_555 1_555 yes O(2) N(1) C(1) 118.1(3) . 1_555 1_555 yes N(1) C(1) C(2) 119.0(3) . 1_555 1_555 yes N(1) C(1) C(6) 118.6(3) . 1_555 1_555 yes C(2) C(1) C(6) 122.4(3) . 1_555 1_555 yes C(1) C(2) C(3) 118.3(3) . 1_555 1_555 yes C(1) C(2) H(1) 117(2) . 1_555 1_555 no C(3) C(2) H(1) 124(2) . 1_555 1_555 no C(2) C(3) C(4) 121.2(3) . 1_555 1_555 yes C(2) C(3) H(2) 118(2) . 1_555 1_555 no C(4) C(3) H(2) 120(2) . 1_555 1_555 no C(3) C(4) C(5) 118.6(3) . 1_555 1_555 yes C(3) C(4) C(7) 119.9(3) . 1_555 1_555 yes C(5) C(4) C(7) 121.5(3) . 1_555 1_555 yes C(4) C(5) C(6) 121.1(3) . 1_555 1_555 yes C(4) C(5) H(3) 116(2) . 1_555 1_555 no C(6) C(5) H(3) 122(2) . 1_555 1_555 no C(1) C(6) C(5) 118.4(3) . 1_555 1_555 yes C(1) C(6) H(4) 122(2) . 1_555 1_555 no C(5) C(6) H(4) 119(2) . 1_555 1_555 no O(3) C(7) C(4) 113.6(3) . 1_555 1_555 yes O(3) C(7) C(8) 105.8(3) . 1_555 1_555 yes O(3) C(7) H(5) 110(1) . 1_555 1_555 no C(4) C(7) C(8) 111.4(3) . 1_555 1_555 yes C(4) C(7) H(5) 109(1) . 1_555 1_555 no C(8) C(7) H(5) 106(1) . 1_555 1_555 no C(7) C(8) C(9) 110.7(3) . 1_555 1_555 yes C(7) C(8) C(10) 109.5(3) . 1_555 1_555 yes C(7) C(8) H(7) 107(2) . 1_555 1_555 no C(9) C(8) C(10) 111.5(3) . 1_555 1_555 yes C(9) C(8) H(7) 109(2) . 1_555 1_555 no C(10) C(8) H(7) 108(2) . 1_555 1_555 no Cl(1) C(9) C(8) 111.8(3) . 1_555 1_555 yes Cl(1) C(9) H(8) 106(2) . 1_555 1_555 no Cl(1) C(9) H(9) 105(1) . 1_555 1_555 no C(8) C(9) H(8) 111(2) . 1_555 1_555 no C(8) C(9) H(9) 105(2) . 1_555 1_555 no H(8) C(9) H(9) 116(2) . 1_555 1_555 no O(4) C(10) C(8) 120.5(4) . 1_555 1_555 yes O(4) C(10) C(11) 121.3(4) . 1_555 1_555 yes C(8) C(10) C(11) 118.2(3) . 1_555 1_555 yes C(10) C(11) H(10) 108(3) . 1_555 1_555 no C(10) C(11) H(11) 113(4) . 1_555 1_555 no C(10) C(11) H(12) 104(4) . 1_555 1_555 no H(10) C(11) H(11) 109(5) . 1_555 1_555 no H(10) C(11) H(12) 105(5) . 1_555 1_555 no H(11) C(11) H(12) 114(6) . 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 Cl(1) C(9) C(8) C(7) 165.1(2) 1_555 1_555 1_555 1_555 yes Cl(1) C(9) C(8) C(10) -72.8(4) 1_555 1_555 1_555 1_555 yes O(1) N(1) C(1) C(2) -168.2(3) 1_555 1_555 1_555 1_555 yes O(1) N(1) C(1) C(6) 11.7(5) 1_555 1_555 1_555 1_555 yes O(2) N(1) C(1) C(2) 11.4(5) 1_555 1_555 1_555 1_555 yes O(2) N(1) C(1) C(6) -168.7(3) 1_555 1_555 1_555 1_555 yes O(3) C(7) C(4) C(3) 165.1(3) 1_555 1_555 1_555 1_555 yes O(3) C(7) C(4) C(5) -16.5(4) 1_555 1_555 1_555 1_555 yes O(3) C(7) C(8) C(9) 60.4(4) 1_555 1_555 1_555 1_555 yes O(3) C(7) C(8) C(10) -62.9(3) 1_555 1_555 1_555 1_555 yes O(4) C(10) C(8) C(7) 115.3(4) 1_555 1_555 1_555 1_555 yes O(4) C(10) C(8) C(9) -7.5(5) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(2) C(3) 179.6(3) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(6) C(5) 179.3(3) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(4) 1.5(5) 1_555 1_555 1_555 1_555 yes C(1) C(6) C(5) C(4) 0.7(5) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(6) C(5) -0.8(5) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(4) C(5) -1.5(5) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(4) C(7) 177.0(3) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(1) C(6) -0.3(5) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(5) C(6) 0.4(5) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(7) C(8) -75.7(4) 1_555 1_555 1_555 1_555 yes C(4) C(7) C(8) C(9) -63.4(4) 1_555 1_555 1_555 1_555 yes C(4) C(7) C(8) C(10) 173.3(3) 1_555 1_555 1_555 1_555 yes C(5) C(4) C(7) C(8) 102.8(4) 1_555 1_555 1_555 1_555 yes C(6) C(5) C(4) C(7) -178.1(3) 1_555 1_555 1_555 1_555 yes C(7) C(8) C(10) C(11) -65.0(5) 1_555 1_555 1_555 1_555 yes C(9) C(8) C(10) C(11) 172.2(4) 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 Cl(1) H(1) 2.96(4) . 1_556 ? Cl(1) H(3) 2.99(4) . 3_544 ? Cl(1) O(1) 3.337(4) . 4_553 ? Cl(1) N(1) 3.431(3) . 3_543 ? Cl(1) H(12) 3.45(7) . 4_543 ? Cl(1) H(2) 3.53(4) . 1_556 ? Cl(1) H(10) 3.53(6) . 4_543 ? Cl(1) O(1) 3.534(3) . 3_543 ? O(1) H(4) 2.73(3) . 2_444 ? O(1) H(7) 2.76(4) . 3_443 ? O(1) H(11) 2.89(8) . 3_443 ? O(1) C(6) 3.399(4) . 2_444 ? O(1) O(2) 3.448(5) . 2_445 ? O(1) C(8) 3.482(5) . 3_443 ? O(1) C(10) 3.501(5) . 3_443 ? O(1) C(11) 3.559(7) . 3_443 ? O(2) H(6) 2.69(5) . 3_543 ? O(2) H(11) 2.85(8) . 4_542 ? O(2) H(4) 2.89(3) . 2_444 ? O(2) O(4) 3.105(4) . 4_543 ? O(2) H(2) 3.25(4) . 4_542 ? O(2) O(3) 3.283(4) . 3_543 ? O(2) H(10) 3.28(6) . 4_542 ? O(2) C(11) 3.471(7) . 4_542 ? O(2) H(7) 3.51(4) . 4_542 ? O(3) O(4) 2.793(4) . 2_454 ? O(3) H(5) 2.90(3) . 2_455 ? O(3) H(10) 3.20(6) . 2_455 ? O(3) H(1) 3.47(4) . 3_443 ? O(3) H(2) 3.59(4) . 2_455 ? O(4) H(5) 2.79(3) . 2_455 ? O(4) N(1) 3.091(4) . 4_553 ? O(4) C(7) 3.098(4) . 2_455 ? O(4) C(1) 3.275(4) . 4_553 ? O(4) C(4) 3.468(4) . 2_455 ? N(1) H(4) 3.16(3) . 2_444 ? N(1) H(6) 3.39(5) . 3_543 ? N(1) H(7) 3.42(4) . 3_443 ? C(1) H(7) 3.56(4) . 3_443 ? C(2) H(3) 3.19(4) . 3_543 ? C(2) H(9) 3.24(4) . 1_554 ? C(2) H(6) 3.52(5) . 3_543 ? C(3) H(9) 3.37(4) . 1_554 ? C(3) H(4) 3.45(3) . 3_543 ? C(3) H(3) 3.49(4) . 3_543 ? C(4) H(12) 3.38(8) . 2_454 ? C(5) H(12) 3.42(8) . 2_454 ? C(5) H(1) 3.44(4) . 3_443 ? C(5) H(11) 3.54(8) . 4_543 ? C(6) H(7) 3.20(4) . 3_443 ? C(6) H(2) 3.45(4) . 3_443 ? C(6) H(11) 3.47(8) . 4_543 ? C(9) H(1) 3.14(4) . 1_556 ? C(9) H(12) 3.39(7) . 4_543 ? C(9) H(11) 3.45(8) . 4_543 ? C(10) H(6) 3.16(5) . 2_455 ? C(10) H(5) 3.32(3) . 2_455 ? C(11) H(8) 2.93(4) . 4_553 ? H(1) H(3) 2.69(5) . 3_543 ? H(1) H(9) 2.87(6) . 1_554 ? H(1) H(6) 3.02(7) . 3_543 ? H(1) H(8) 3.12(6) . 1_554 ? H(1) H(11) 3.49(9) . 4_542 ? H(2) H(4) 2.90(5) . 3_543 ? H(2) H(9) 3.05(5) . 1_554 ? H(2) H(3) 3.28(5) . 3_543 ? H(2) H(6) 3.38(6) . 2_454 ? H(4) H(7) 2.79(5) . 3_443 ? H(4) H(11) 3.56(8) . 4_543 ? H(5) H(6) 3.23(6) . 2_454 ? H(5) H(9) 3.32(5) . 2_454 ? H(6) H(9) 3.44(6) . 2_454 ? H(6) H(10) 3.45(8) . 2_455 ? H(6) H(12) 3.60(9) . 2_454 ? H(8) H(11) 2.57(8) . 4_543 ? H(8) H(12) 2.63(8) . 4_543 ? H(8) H(10) 3.26(7) . 4_543 ? H(9) H(10) 3.30(7) . 2_455 ? #------------------------------------------------------------------------------