# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _publ_contact_author_email DBSC@UOHYD.ERNET.IN _publ_contact_author_name 'Prof Deevi Basavaiah' _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_address ; School of Chemistry University of Hyderabad Central University (PO) HYDERABAD Andhra Pradesh 500 046 INDIA ; _publ_section_title ; A Novel, Tandem Construction of C-N and C-C Bonds: Facile and One-Pot Transformation of the Baylis-Hillman Adducts into 2-Benzazepines ; loop_ _publ_author_name 'Deevi Basavaiah' 'Tummanapalli Satyanarayana' data_13 _database_code_depnum_ccdc_archive 'CCDC 211673' _chemical_name_common ; 3-Aza-2-ethyl-5-methoxycarbonyl-9,10,11- trimethoxybicyclo(5.4.0)undeca-1(7),2,5,8,10-pentaene ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-Aza-2-ethyl-5-methoxycarbonyl-9,10,11- trimethoxybicyclo[5.4.0]undeca-1(7),2,5,8,10- pentaene ; _chemical_melting_point '140 centigrades' _chemical_formula_moiety ? _chemical_formula_sum 'C17 H21 N O5' _chemical_formula_weight 319.35 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 C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/a _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 10.669(6) _cell_length_b 13.041(8) _cell_length_c 12.062(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.18(5) _cell_angle_gamma 90.00 _cell_volume 1675.6(18) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rectangular _exptl_crystal_colour 'light Yellow' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3791 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 28.74 _reflns_number_total 3791 _reflns_number_gt 1667 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1966P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.010(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3791 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1198 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.2709 _refine_ls_wR_factor_gt 0.1845 _refine_ls_goodness_of_fit_ref 0.854 _refine_ls_restrained_S_all 0.854 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7227(2) 1.00379(19) 0.8334(2) 0.0460(6) Uani 1 1 d . . . C2 C 0.7110(3) 1.0081(2) 0.7158(2) 0.0473(7) Uani 1 1 d . . . C3 C 0.7582(3) 1.0897(2) 0.6619(2) 0.0509(7) Uani 1 1 d . . . C4 C 0.8160(3) 1.1725(2) 0.7253(2) 0.0519(7) Uani 1 1 d . . . C5 C 0.8304(3) 1.1695(2) 0.8397(2) 0.0499(7) Uani 1 1 d . . . H5 H 0.8679 1.2240 0.8788 0.060 Uiso 1 1 calc R . . C6 C 0.7886(3) 1.0848(2) 0.8954(2) 0.0461(6) Uani 1 1 d . . . C7 C 0.8197(3) 1.0840(2) 1.0180(2) 0.0521(7) Uani 1 1 d . . . H7 H 0.8242 1.1470 1.0542 0.063 Uiso 1 1 calc R . . C8 C 0.8419(3) 0.9993(2) 1.0802(2) 0.0510(7) Uani 1 1 d . . . C9 C 0.8315(3) 0.8959(2) 1.0250(3) 0.0531(7) Uani 1 1 d . . . H9A H 0.8561 0.8429 1.0783 0.064 Uiso 1 1 calc R . . H9B H 0.8880 0.8928 0.9648 0.064 Uiso 1 1 calc R . . C10 C 0.6517(3) 0.9262(2) 0.8911(2) 0.0486(7) Uani 1 1 d . . . C11 C 0.5108(3) 0.9161(3) 0.8479(3) 0.0636(8) Uani 1 1 d . . . H11A H 0.4638 0.9727 0.8773 0.076 Uiso 1 1 calc R . . H11B H 0.5061 0.9223 0.7676 0.076 Uiso 1 1 calc R . . C12 C 0.4508(3) 0.8194(3) 0.8781(4) 0.0864(12) Uani 1 1 d . . . H12A H 0.3650 0.8192 0.8495 0.130 Uiso 1 1 calc R . . H12B H 0.4536 0.8130 0.9575 0.130 Uiso 1 1 calc R . . H12C H 0.4946 0.7630 0.8470 0.130 Uiso 1 1 calc R . . C13 C 0.7204(5) 0.8399(3) 0.6443(4) 0.0957(13) Uani 1 1 d . . . H13A H 0.6746 0.7911 0.5983 0.144 Uiso 1 1 calc R . . H13B H 0.7349 0.8121 0.7176 0.144 Uiso 1 1 calc R . . H13C H 0.7993 0.8544 0.6132 0.144 Uiso 1 1 calc R . . C14 C 0.6426(4) 1.1171(3) 0.4802(3) 0.0844(11) Uani 1 1 d . . . H14A H 0.6581 1.1115 0.4029 0.127 Uiso 1 1 calc R . . H14B H 0.6201 1.1864 0.4969 0.127 Uiso 1 1 calc R . . H14C H 0.5751 1.0720 0.4972 0.127 Uiso 1 1 calc R . . C15 C 0.9235(4) 1.3328(3) 0.7231(3) 0.0764(10) Uani 1 1 d . . . H15A H 0.9480 1.3837 0.6710 0.115 Uiso 1 1 calc R . . H15B H 0.9969 1.3056 0.7622 0.115 Uiso 1 1 calc R . . H15C H 0.8698 1.3635 0.7750 0.115 Uiso 1 1 calc R . . C16 C 0.8740(3) 1.0125(3) 1.2041(3) 0.0625(8) Uani 1 1 d . . . C17 C 0.9111(4) 0.9275(3) 1.3798(3) 0.0889(13) Uani 1 1 d . . . H17A H 0.9165 0.8592 1.4094 0.133 Uiso 1 1 calc R . . H17B H 0.8454 0.9642 1.4140 0.133 Uiso 1 1 calc R . . H17C H 0.9895 0.9622 1.3948 0.133 Uiso 1 1 calc R . . O1 O 0.6502(2) 0.93114(15) 0.64998(18) 0.0640(6) Uani 1 1 d . . . O2 O 0.7568(2) 1.08832(19) 0.54748(17) 0.0705(7) Uani 1 1 d . . . O3 O 0.8562(2) 1.24996(17) 0.66357(18) 0.0691(7) Uani 1 1 d . . . O4 O 0.8893(4) 1.0929(2) 1.2520(2) 0.1152(13) Uani 1 1 d . . . O5 O 0.8829(2) 0.92264(18) 1.25820(17) 0.0683(7) Uani 1 1 d . . . N1 N 0.6969(2) 0.87700(18) 0.9797(2) 0.0529(6) Uani 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0455(14) 0.0442(14) 0.0483(15) 0.0002(11) 0.0038(11) -0.0023(11) C2 0.0474(14) 0.0475(15) 0.0471(15) -0.0056(11) 0.0033(11) 0.0014(11) C3 0.0494(15) 0.0610(17) 0.0428(15) -0.0032(12) 0.0072(11) 0.0000(12) C4 0.0525(15) 0.0525(16) 0.0521(16) 0.0016(13) 0.0147(12) -0.0080(12) C5 0.0553(16) 0.0491(15) 0.0459(15) -0.0047(12) 0.0075(12) -0.0071(12) C6 0.0487(14) 0.0457(14) 0.0446(15) -0.0040(11) 0.0085(11) -0.0001(11) C7 0.0566(16) 0.0510(15) 0.0496(16) -0.0070(12) 0.0119(12) -0.0057(13) C8 0.0496(15) 0.0570(16) 0.0465(16) -0.0038(12) 0.0045(12) -0.0006(12) C9 0.0558(17) 0.0537(16) 0.0494(16) -0.0009(13) -0.0008(13) 0.0057(13) C10 0.0517(15) 0.0417(13) 0.0523(16) 0.0008(12) 0.0021(12) -0.0048(12) C11 0.0559(18) 0.0646(19) 0.070(2) 0.0115(15) -0.0045(15) -0.0086(15) C12 0.058(2) 0.071(2) 0.130(4) 0.020(2) 0.006(2) -0.0119(17) C13 0.121(3) 0.063(2) 0.102(3) -0.033(2) -0.002(3) 0.008(2) C14 0.095(3) 0.106(3) 0.0511(19) 0.0139(19) -0.0057(18) -0.002(2) C15 0.086(3) 0.062(2) 0.083(2) 0.0032(18) 0.0200(19) -0.0268(18) C16 0.066(2) 0.072(2) 0.0497(17) -0.0030(16) 0.0070(14) -0.0073(16) C17 0.104(3) 0.115(3) 0.049(2) 0.007(2) 0.0074(19) 0.016(2) 01 0.0740(15) 0.0538(12) 0.0629(14) -0.0147(10) -0.0071(11) -0.0030(10) O2 0.0729(15) 0.0947(18) 0.0450(12) -0.0052(11) 0.0135(10) -0.0028(12) O3 0.0803(16) 0.0653(14) 0.0634(14) 0.0078(11) 0.0190(11) -0.0176(11) O4 0.210(4) 0.0810(19) 0.0541(16) -0.0133(14) 0.0057(19) -0.021(2) O5 0.0808(16) 0.0784(15) 0.0462(12) 0.0021(11) 0.0068(11) 0.0058(12) N1 0.0563(14) 0.0466(13) 0.0558(14) 0.0040(11) 0.0023(11) -0.0034(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.418(4) . ? C1 C6 1.453(4) . ? C1 C10 1.463(4) . ? C2 C3 1.358(4) . ? C2 01 1.415(3) . ? C3 O2 1.380(3) . ? C3 C4 1.442(4) . ? C4 O3 1.339(3) . ? C4 C5 1.381(4) . ? C5 C6 1.380(4) . ? C6 C7 1.498(4) . ? C7 C8 1.348(4) . ? C8 C9 1.505(4) . ? C8 C16 1.524(4) . ? C9 N1 1.528(4) . ? C10 N1 1.315(4) . ? C10 C11 1.569(4) . ? C11 C12 1.469(4) . ? C13 01 1.409(4) . ? C14 O2 1.474(5) . ? C15 O3 1.463(4) . ? C16 O4 1.205(4) . ? C16 O5 1.342(4) . ? C17 O5 1.482(4) . ? 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_3 _geom_angle_publ_flag C2 C1 C6 119.9(2) . . ? C2 C1 C10 119.0(2) . . ? C6 C1 C10 120.4(2) . . ? C3 C2 01 117.2(3) . . ? C3 C2 C1 119.7(2) . . ? 01 C2 C1 123.1(2) . . ? C2 C3 O2 119.0(3) . . ? C2 C3 C4 119.5(3) . . ? O2 C3 C4 121.4(3) . . ? O3 C4 C5 123.7(3) . . ? O3 C4 C3 114.3(3) . . ? C5 C4 C3 122.0(3) . . ? C6 C5 C4 119.2(3) . . ? C5 C6 C1 119.5(2) . . ? C5 C6 C7 115.2(2) . . ? C1 C6 C7 125.3(2) . . ? C8 C7 C6 125.3(3) . . ? C7 C8 C9 118.8(3) . . ? C7 C8 C16 118.4(3) . . ? C9 C8 C16 122.8(3) . . ? C8 C9 N1 110.3(2) . . ? N1 C10 C1 123.2(3) . . ? N1 C10 C11 122.1(3) . . ? C1 C10 C11 114.3(2) . . ? C12 C11 C10 114.3(3) . . ? O4 C16 O5 121.5(3) . . ? O4 C16 C8 125.9(3) . . ? O5 C16 C8 112.6(3) . . ? C2 01 C13 113.4(3) . . ? C3 O2 C14 120.7(3) . . ? C4 O3 C15 116.6(3) . . ? C16 O5 C17 116.7(3) . . ? C10 N1 C9 120.5(2) . . ? _diffrn_measured_fraction_theta_max 0.872 _diffrn_reflns_theta_full 28.74 _diffrn_measured_fraction_theta_full 0.872 _refine_diff_density_max 0.310 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.048 #===END data_15 _database_code_depnum_ccdc_archive 'CCDC 211674' _chemical_name_common ; 3-Aza-2-ethyl-5-methoxycarbonyl-9,10- methylenedioxybicyclo(5.4.0)undeca-1(7),2,5,8,10-pentaene ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-Aza-2-ethyl-5-methoxycarbonyl-9,10- methylenedioxybicyclo[5.4.0]undeca- 1(7),2,5,8,10-pentaene ; _chemical_melting_point '126 centigrades' _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 N O4' _chemical_formula_weight 273.28 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 C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/a _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 8.096(5) _cell_length_b 16.436(8) _cell_length_c 10.159(8) _cell_angle_alpha 90.00 _cell_angle_beta 98.73(5) _cell_angle_gamma 90.00 _cell_volume 1336.1(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rectangular _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3881 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 29.96 _reflns_number_total 3881 _reflns_number_gt 2494 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0539P)^2^+0.2643P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.037(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3881 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0795 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1254 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.97354(14) 0.17761(7) 0.67261(11) 0.0391(3) Uani 1 1 d . . . O4 O 0.85858(15) -0.01253(7) 0.83094(10) 0.0564(3) Uani 1 1 d . . . O2 O 0.92370(17) 0.24189(8) 0.07719(11) 0.0626(3) Uani 1 1 d . . . O1 O 0.75371(17) 0.12944(8) 0.02906(10) 0.0610(3) Uani 1 1 d . . . O3 O 0.63534(16) -0.04482(8) 0.68324(12) 0.0651(4) Uani 1 1 d . . . C2 C 0.83610(17) 0.04788(8) 0.61943(13) 0.0377(3) Uani 1 1 d . . . C4 C 0.80061(17) 0.11362(8) 0.39662(13) 0.0369(3) Uani 1 1 d . . . C6 C 0.74829(18) 0.06053(8) 0.49832(14) 0.0386(3) Uani 1 1 d . . . H6 H 0.6467 0.0336 0.4774 0.046 Uiso 1 1 calc R . . C7 C 0.93216(16) 0.21833(8) 0.56531(13) 0.0369(3) Uani 1 1 d . . . C8 C 0.89795(16) 0.18456(8) 0.42661(13) 0.0375(3) Uani 1 1 d . . . C9 C 0.76434(19) -0.00781(9) 0.71149(14) 0.0417(3) Uani 1 1 d . . . C11 C 0.74127(19) 0.09255(9) 0.26242(14) 0.0424(3) Uani 1 1 d . . . H11 H 0.6713 0.0480 0.2417 0.051 Uiso 1 1 calc R . . C13 C 0.9435(2) 0.23203(10) 0.32127(14) 0.0466(4) Uani 1 1 d . . . H13 H 1.0077 0.2788 0.3386 0.056 Uiso 1 1 calc R . . C14 C 1.00065(18) 0.08991(9) 0.65773(14) 0.0409(3) Uani 1 1 d . . . H14A H 1.0573 0.0677 0.7410 0.049 Uiso 1 1 calc R . . H14B H 1.0708 0.0808 0.5897 0.049 Uiso 1 1 calc R . . C15 C 0.9071(2) 0.30930(9) 0.57625(15) 0.0463(3) Uani 1 1 d . . . H15A H 0.9844 0.3366 0.5267 0.056 Uiso 1 1 calc R . . H15B H 0.7949 0.3225 0.5336 0.056 Uiso 1 1 calc R . . C16 C 0.8904(2) 0.20717(10) 0.19373(14) 0.0462(4) Uani 1 1 d . . . C17 C 0.7899(2) 0.13958(9) 0.16478(14) 0.0452(3) Uani 1 1 d . . . C18 C 0.9309(3) 0.34326(10) 0.71519(17) 0.0630(5) Uani 1 1 d . . . H18A H 0.9124 0.4010 0.7115 0.094 Uiso 1 1 calc R . . H18B H 1.0428 0.3324 0.7579 0.094 Uiso 1 1 calc R . . H18C H 0.8528 0.3181 0.7649 0.094 Uiso 1 1 calc R . . C19 C 0.8126(3) 0.20190(11) -0.02654(16) 0.0615(5) Uani 1 1 d . . . H19A H 0.7195 0.2372 -0.0593 0.074 Uiso 1 1 calc R . . H19B H 0.8712 0.1884 -0.1002 0.074 Uiso 1 1 calc R . . C20 C 0.7953(3) -0.06429(13) 0.92713(18) 0.0736(6) Uani 1 1 d . . . H20A H 0.8718 -0.0638 1.0091 0.110 Uiso 1 1 calc R . . H20B H 0.7836 -0.1189 0.8933 0.110 Uiso 1 1 calc R . . H20C H 0.6884 -0.0445 0.9428 0.110 Uiso 1 1 calc 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 N1 0.0396(6) 0.0387(6) 0.0393(6) 0.0002(5) 0.0075(5) -0.0021(5) O4 0.0632(7) 0.0603(7) 0.0444(6) 0.0147(5) 0.0037(5) -0.0122(6) O2 0.0828(9) 0.0686(8) 0.0392(6) 0.0067(5) 0.0187(6) -0.0185(6) O1 0.0889(9) 0.0602(7) 0.0352(6) -0.0027(5) 0.0138(6) -0.0120(6) O3 0.0634(8) 0.0725(8) 0.0576(7) 0.0163(6) 0.0033(6) -0.0259(6) C2 0.0415(7) 0.0331(6) 0.0401(7) 0.0009(5) 0.0116(6) 0.0025(5) C4 0.0381(7) 0.0360(7) 0.0380(7) 0.0010(5) 0.0107(5) 0.0018(5) C6 0.0407(7) 0.0358(7) 0.0409(7) -0.0005(6) 0.0110(6) -0.0014(5) C7 0.0349(6) 0.0380(7) 0.0387(7) 0.0003(5) 0.0091(5) -0.0040(5) C8 0.0371(7) 0.0391(7) 0.0373(7) 0.0014(5) 0.0088(5) -0.0003(6) C9 0.0467(8) 0.0375(7) 0.0418(7) 0.0031(6) 0.0101(6) 0.0008(6) C11 0.0485(8) 0.0391(7) 0.0409(7) -0.0028(6) 0.0103(6) -0.0035(6) C13 0.0514(8) 0.0472(8) 0.0429(8) 0.0024(6) 0.0123(6) -0.0101(7) C14 0.0396(7) 0.0390(7) 0.0443(8) 0.0047(6) 0.0074(6) 0.0026(6) C15 0.0546(9) 0.0359(7) 0.0491(8) 0.0012(6) 0.0097(7) -0.0026(6) C16 0.0542(9) 0.0476(8) 0.0397(7) 0.0051(6) 0.0166(6) -0.0036(7) C17 0.0537(8) 0.0482(8) 0.0352(7) -0.0032(6) 0.0115(6) 0.0008(7) C18 0.0862(13) 0.0425(9) 0.0575(10) -0.0081(8) 0.0026(9) 0.0030(9) C19 0.0823(12) 0.0661(11) 0.0383(8) 0.0033(8) 0.0160(8) -0.0065(9) C20 0.0911(15) 0.0765(13) 0.0521(10) 0.0249(9) 0.0071(10) -0.0192(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C7 1.2797(19) . ? N1 C14 1.469(2) . ? O4 C9 1.334(2) . ? O4 C20 1.447(2) . ? O2 C16 1.3773(19) . ? O2 C19 1.436(2) . ? O1 C17 1.375(2) . ? O1 C19 1.431(2) . ? O3 C9 1.205(2) . ? C2 C6 1.340(2) . ? C2 C9 1.488(2) . ? C2 C14 1.499(2) . ? C4 C8 1.414(2) . ? C4 C11 1.418(2) . ? C4 C6 1.463(2) . ? C7 C8 1.500(2) . ? C7 C15 1.515(2) . ? C8 C13 1.418(2) . ? C11 C17 1.362(2) . ? C13 C16 1.364(2) . ? C15 C18 1.503(2) . ? C16 C17 1.382(2) . ? 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_3 _geom_angle_publ_flag C7 N1 C14 116.70(12) . . ? C9 O4 C20 115.87(14) . . ? C16 O2 C19 104.98(13) . . ? C17 O1 C19 105.18(12) . . ? C6 C2 C9 117.97(14) . . ? C6 C2 C14 119.57(13) . . ? C9 C2 C14 122.47(13) . . ? C8 C4 C11 120.32(12) . . ? C8 C4 C6 123.44(13) . . ? C11 C4 C6 116.17(13) . . ? C2 C6 C4 124.79(14) . . ? N1 C7 C8 126.41(13) . . ? N1 C7 C15 118.31(13) . . ? C8 C7 C15 115.23(12) . . ? C4 C8 C13 119.42(13) . . ? C4 C8 C7 121.64(12) . . ? C13 C8 C7 118.24(13) . . ? O3 C9 O4 122.86(14) . . ? O3 C9 C2 124.59(14) . . ? O4 C9 C2 112.55(13) . . ? C17 C11 C4 117.93(14) . . ? C16 C13 C8 118.14(14) . . ? N1 C14 C2 109.77(11) . . ? C18 C15 C7 115.84(13) . . ? C13 C16 O2 128.15(15) . . ? C13 C16 C17 122.22(13) . . ? O2 C16 C17 109.63(14) . . ? C11 C17 O1 128.33(15) . . ? C11 C17 C16 121.81(14) . . ? O1 C17 C16 109.85(13) . . ? O1 C19 O2 107.49(13) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.96 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.254 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.035 #===END