# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Sanjay Trehan' 'Prasad V. Bharatam' 'Soma Ghosh' Nancy 'Gurmeet Kaur Nanda' 'Nishan Singh' P.Venupopalan _publ_contact_author_name 'Dr Sanjay Trehan' _publ_contact_author_address ; Department of Chemistry Panjab University Sector 14 Chandigarh U. T. 160 014 INDIA ; _publ_contact_author_phone '091 40 23045439' _publ_contact_author_fax '091 40 23045438' _publ_contact_author_email trehan_s@yahoo.com _publ_requested_journal 'Chemical Communications' _publ_section_title ; Origin of 1,3-induction in alkyl lithium addition to imines bearing N-stereogenic center ; _publ_requested_coeditor_name ? #============================================================================ data_nan1 _database_code_CSD 201482 _audit_creation_method 'Manual edit of SHELXL-97 CIF' _chemical_name_systematic ; ? ; _chemical_name_common "N(1'-phenethyl)-1-phenylpropylamine hydrocholride" _chemical_melting_point 491-493 _chemical_formula_moiety ? _chemical_formula_sum 'C17 H22 Cl N' _chemical_formula_weight 275.81 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.098(4) _cell_length_b 8.006(2) _cell_length_c 18.969(9) _cell_angle_alpha 90.00 _cell_angle_beta 101.97(3) _cell_angle_gamma 90.00 _cell_volume 1648.8(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 28 _cell_measurement_theta_min 10.425 _cell_measurement_theta_max 23.812 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_preparation 'ethanol:acetonitrile, 1:1' _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.111 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.220 _exptl_absorpt_correction_type None _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 'Siemens P4' _diffrn_measurement_method '2\q/\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% None _diffrn_reflns_number 2373 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 23.01 _reflns_number_total 2251 _reflns_number_gt 1510 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Siemens)' _computing_cell_refinement 'XSCANS (Siemens)' _computing_data_reduction 'XSCANS (Siemens)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Siemens)' _computing_publication_material SHELXL-97 _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^)+(0.1046P)^2^+0.5252P] 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 0.009(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2251 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0961 _refine_ls_R_factor_gt 0.0629 _refine_ls_wR_factor_ref 0.1845 _refine_ls_wR_factor_gt 0.1598 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 0.0871(2) 0.8360(4) 0.93368(17) 0.0633(9) Uani 1 1 d . . . H1A H 0.0080 0.8316 0.9382 0.076 Uiso 1 1 calc R . . H1B H 0.1242 0.9163 0.9637 0.076 Uiso 1 1 calc R . . C1 C 0.0889(3) 0.8885(5) 0.8584(2) 0.0727(11) Uani 1 1 d . . . H1C H 0.1751 0.9019 0.8546 0.087 Uiso 1 1 calc R . . C2 C 0.0263(5) 1.0607(6) 0.8464(3) 0.0973(15) Uani 1 1 d . . . H2A H -0.0602 1.0476 0.8473 0.117 Uiso 1 1 calc R . . H2B H 0.0624 1.1331 0.8862 0.117 Uiso 1 1 calc R . . C3 C 0.0354(8) 1.1379(9) 0.7830(5) 0.173(3) Uani 1 1 d . . . H3A H 0.1207 1.1532 0.7816 0.260 Uiso 1 1 calc R . . H3B H -0.0047 1.2447 0.7801 0.260 Uiso 1 1 calc R . . H3C H -0.0034 1.0699 0.7430 0.260 Uiso 1 1 calc R . . C4 C 0.1463(3) 0.6730(4) 0.9587(2) 0.0655(11) Uani 1 1 d . . . H4A H 0.0982 0.5846 0.9301 0.079 Uiso 1 1 calc R . . C5 C 0.1411(4) 0.6430(6) 1.0374(3) 0.0988(15) Uani 1 1 d . . . H5A H 0.1873 0.7282 1.0668 0.148 Uiso 1 1 calc R . . H5B H 0.1757 0.5356 1.0522 0.148 Uiso 1 1 calc R . . H5C H 0.0570 0.6463 1.0427 0.148 Uiso 1 1 calc R . . C6 C 0.2762(3) 0.6636(4) 0.9458(2) 0.0594(9) Uani 1 1 d . . . C7 C 0.3637(3) 0.7836(5) 0.9747(2) 0.0726(11) Uani 1 1 d . . . H7A H 0.3424 0.8708 1.0022 0.087 Uiso 1 1 calc R . . C8 C 0.4823(3) 0.7729(6) 0.9626(3) 0.0815(13) Uani 1 1 d . . . H8A H 0.5396 0.8550 0.9808 0.098 Uiso 1 1 calc R . . C9 C 0.5156(3) 0.6448(6) 0.9245(2) 0.0763(12) Uani 1 1 d . . . H9A H 0.5955 0.6387 0.9168 0.092 Uiso 1 1 calc R . . C10 C 0.4325(4) 0.5254(6) 0.8977(2) 0.0796(12) Uani 1 1 d . . . H10A H 0.4561 0.4361 0.8722 0.095 Uiso 1 1 calc R . . C11 C 0.3121(3) 0.5346(5) 0.9077(2) 0.0715(11) Uani 1 1 d . . . H11A H 0.2556 0.4525 0.8883 0.086 Uiso 1 1 calc R . . C12 C 0.0301(3) 0.7619(5) 0.8028(2) 0.0739(11) Uani 1 1 d . . . C13 C 0.0967(5) 0.6958(6) 0.7558(3) 0.0939(14) Uani 1 1 d . . . H13A H 0.1793 0.7240 0.7606 0.113 Uiso 1 1 calc R . . C14 C 0.0428(7) 0.5892(8) 0.7021(3) 0.1184(19) Uani 1 1 d . . . H14A H 0.0885 0.5479 0.6700 0.142 Uiso 1 1 calc R . . C15 C -0.0767(8) 0.5432(8) 0.6953(3) 0.127(2) Uani 1 1 d . . . H15A H -0.1129 0.4707 0.6587 0.152 Uiso 1 1 calc R . . C16 C -0.1424(6) 0.6031(8) 0.7417(4) 0.128(2) Uani 1 1 d . . . H16A H -0.2243 0.5714 0.7370 0.154 Uiso 1 1 calc R . . C17 C -0.0897(4) 0.7117(7) 0.7966(3) 0.1010(15) Uani 1 1 d . . . H17A H -0.1357 0.7502 0.8290 0.121 Uiso 1 1 calc R . . Cl1 Cl -0.18033(8) 0.85873(14) 0.96453(7) 0.0893(5) 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 N1 0.0337(14) 0.069(2) 0.085(2) -0.0181(17) 0.0077(13) -0.0044(13) C1 0.047(2) 0.075(3) 0.093(3) -0.006(2) 0.0069(19) 0.0061(18) C2 0.089(3) 0.075(3) 0.124(4) 0.005(3) 0.015(3) 0.014(3) C3 0.220(9) 0.139(6) 0.183(7) 0.057(5) 0.093(6) 0.058(6) C4 0.0400(19) 0.061(2) 0.094(3) -0.008(2) 0.0090(18) -0.0058(16) C5 0.066(3) 0.122(4) 0.119(4) 0.002(3) 0.042(3) -0.015(3) C6 0.0402(18) 0.059(2) 0.079(2) 0.0006(19) 0.0108(16) 0.0009(16) C7 0.0392(19) 0.066(2) 0.112(3) -0.014(2) 0.0135(19) -0.0017(18) C8 0.0381(19) 0.076(3) 0.130(4) 0.003(3) 0.017(2) -0.0044(19) C9 0.044(2) 0.087(3) 0.101(3) 0.011(3) 0.020(2) 0.012(2) C10 0.067(3) 0.085(3) 0.089(3) -0.005(2) 0.020(2) 0.021(2) C11 0.054(2) 0.069(3) 0.087(3) -0.009(2) 0.0041(19) 0.0030(19) C12 0.059(2) 0.074(3) 0.083(3) -0.002(2) 0.001(2) 0.017(2) C13 0.090(3) 0.100(3) 0.088(3) -0.005(3) 0.010(3) 0.021(3) C14 0.139(5) 0.125(5) 0.087(4) -0.009(3) 0.015(4) 0.036(4) C15 0.147(6) 0.114(5) 0.102(4) -0.029(3) -0.016(4) 0.022(4) C16 0.090(4) 0.133(5) 0.141(5) -0.042(4) -0.024(4) -0.001(3) C17 0.061(3) 0.124(4) 0.109(4) -0.039(3) -0.002(2) 0.000(3) Cl1 0.0355(5) 0.0983(9) 0.1338(10) -0.0454(7) 0.0166(5) -0.0104(5) _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 C1 1.492(5) . ? N1 C4 1.494(4) . ? C1 C12 1.511(6) . ? C1 C2 1.539(6) . ? C2 C3 1.374(8) . ? C4 C6 1.513(5) . ? C4 C5 1.524(6) . ? C6 C11 1.366(5) . ? C6 C7 1.395(5) . ? C7 C8 1.385(5) . ? C8 C9 1.349(6) . ? C9 C10 1.353(6) . ? C10 C11 1.390(5) . ? C12 C17 1.370(6) . ? C12 C13 1.376(6) . ? C13 C14 1.368(8) . ? C14 C15 1.356(8) . ? C15 C16 1.343(8) . ? C16 C17 1.389(7) . ? 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 C1 N1 C4 117.2(3) . . ? N1 C1 C12 113.0(3) . . ? N1 C1 C2 107.4(3) . . ? C12 C1 C2 112.4(3) . . ? C3 C2 C1 114.9(5) . . ? N1 C4 C6 111.3(3) . . ? N1 C4 C5 110.2(3) . . ? C6 C4 C5 112.4(3) . . ? C11 C6 C7 118.2(3) . . ? C11 C6 C4 121.0(3) . . ? C7 C6 C4 120.7(3) . . ? C8 C7 C6 120.0(4) . . ? C9 C8 C7 120.8(4) . . ? C8 C9 C10 119.9(4) . . ? C9 C10 C11 120.7(4) . . ? C6 C11 C10 120.5(4) . . ? C17 C12 C13 118.3(4) . . ? C17 C12 C1 121.9(4) . . ? C13 C12 C1 119.9(4) . . ? C14 C13 C12 120.8(5) . . ? C15 C14 C13 120.5(6) . . ? C16 C15 C14 119.6(6) . . ? C15 C16 C17 120.9(6) . . ? C12 C17 C16 119.9(5) . . ? 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 C4 N1 C1 C12 57.1(4) . . . . ? C4 N1 C1 C2 -178.4(3) . . . . ? N1 C1 C2 C3 171.3(5) . . . . ? C12 C1 C2 C3 -63.8(7) . . . . ? C1 N1 C4 C6 52.1(4) . . . . ? C1 N1 C4 C5 177.5(3) . . . . ? N1 C4 C6 C11 -125.4(4) . . . . ? C5 C4 C6 C11 110.4(4) . . . . ? N1 C4 C6 C7 56.9(5) . . . . ? C5 C4 C6 C7 -67.3(5) . . . . ? C11 C6 C7 C8 2.0(6) . . . . ? C4 C6 C7 C8 179.8(4) . . . . ? C6 C7 C8 C9 -1.8(6) . . . . ? C7 C8 C9 C10 0.2(7) . . . . ? C8 C9 C10 C11 1.2(6) . . . . ? C7 C6 C11 C10 -0.7(6) . . . . ? C4 C6 C11 C10 -178.5(3) . . . . ? C9 C10 C11 C6 -0.9(6) . . . . ? N1 C1 C12 C17 58.2(5) . . . . ? C2 C1 C12 C17 -63.5(6) . . . . ? N1 C1 C12 C13 -122.8(4) . . . . ? C2 C1 C12 C13 115.5(4) . . . . ? C17 C12 C13 C14 3.2(7) . . . . ? C1 C12 C13 C14 -175.8(4) . . . . ? C12 C13 C14 C15 -1.7(8) . . . . ? C13 C14 C15 C16 0.0(10) . . . . ? C14 C15 C16 C17 0.1(10) . . . . ? C13 C12 C17 C16 -3.1(7) . . . . ? C1 C12 C17 C16 175.9(5) . . . . ? C15 C16 C17 C12 1.5(9) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 23.01 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.360 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.047 #===END data_nancy6 _database_code_CSD 201483 _audit_creation_method 'Manual edit of SHELXL-97 CIF' _chemical_name_systematic ; ? ; _chemical_name_common ; N-(1'-phenethyl)2-methyl-1-phenylpropylamine-p-nitro benzoate salt ; _chemical_melting_point 488 _chemical_formula_moiety ? _chemical_formula_sum 'C25 H28 N2 O4' _chemical_formula_weight 420.49 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6310(10) _cell_length_b 12.435(2) _cell_length_c 12.704(2) _cell_angle_alpha 117.720(10) _cell_angle_beta 101.030(10) _cell_angle_gamma 96.190(10) _cell_volume 1153.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 40 _cell_measurement_theta_min 9.882 _cell_measurement_theta_max 29.539 _exptl_crystal_description 'elongated plate' _exptl_crystal_colour colourless _exptl_crystal_preparation Ethanol _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.210 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type None _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 'Siemens P4' _diffrn_measurement_method 2\q/\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% None _diffrn_reflns_number 3692 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 24.00 _reflns_number_total 3418 _reflns_number_gt 2730 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XSCANS (Siemens)' _computing_cell_refinement 'XSCANS (Siemens)' _computing_data_reduction 'XSCANS (Siemens)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Siemens)' _computing_publication_material SHELXL-97 _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^)+(0.0598P)^2^+0.2281P] 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 0.008(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3418 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0560 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1230 _refine_ls_wR_factor_gt 0.1127 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 O1 O 0.50337(18) 1.86846(13) 1.25596(13) 0.0676(4) Uani 1 1 d . . . O2 O 0.64624(19) 1.83319(14) 1.39651(12) 0.0722(4) Uani 1 1 d . . . O3 O 0.7683(3) 1.41235(17) 0.81121(18) 0.1077(7) Uani 1 1 d . . . O4 O 0.8754(2) 1.36071(16) 0.94354(19) 0.0972(6) Uani 1 1 d . . . N1 N 0.58380(17) 0.91356(13) 0.62180(12) 0.0431(4) Uani 1 1 d . . . H1A H 0.6196 0.9022 0.5561 0.052 Uiso 1 1 calc R . . H1C H 0.5482 0.9846 0.6485 0.052 Uiso 1 1 calc R . . N2 N 0.8010(2) 1.42539(17) 0.91416(19) 0.0733(5) Uani 1 1 d . . . C1 C 0.7259(2) 0.93186(15) 0.72251(15) 0.0425(4) Uani 1 1 d . . . H1B H 0.6875 0.9567 0.7965 0.051 Uiso 1 1 calc R . . C2 C 0.7815(2) 0.81269(16) 0.69607(16) 0.0457(4) Uani 1 1 d . . . C3 C 0.8065(3) 0.73357(19) 0.58388(18) 0.0650(6) Uani 1 1 d . . . H3A H 0.7885 0.7525 0.5205 0.078 Uiso 1 1 calc R . . C4 C 0.8584(3) 0.6258(2) 0.5653(2) 0.0862(8) Uani 1 1 d . . . H4A H 0.8745 0.5726 0.4894 0.103 Uiso 1 1 calc R . . C5 C 0.8858(3) 0.5975(2) 0.6581(3) 0.0866(8) Uani 1 1 d . . . H5A H 0.9200 0.5250 0.6449 0.104 Uiso 1 1 calc R . . C6 C 0.8632(3) 0.6750(2) 0.7700(2) 0.0762(7) Uani 1 1 d . . . H6A H 0.8835 0.6563 0.8335 0.091 Uiso 1 1 calc R . . C7 C 0.8100(2) 0.78135(19) 0.78816(19) 0.0576(5) Uani 1 1 d . . . H7A H 0.7928 0.8332 0.8641 0.069 Uiso 1 1 calc R . . C8 C 0.8590(2) 1.04318(17) 0.75292(17) 0.0540(5) Uani 1 1 d . . . H8A H 0.8062 1.1115 0.7608 0.065 Uiso 1 1 calc R . . C9 C 0.9498(3) 1.0191(2) 0.6553(2) 0.0786(7) Uani 1 1 d . . . H9A H 1.0195 1.0957 0.6761 0.118 Uiso 1 1 calc R . . H9B H 0.8734 0.9867 0.5761 0.118 Uiso 1 1 calc R . . H9C H 1.0137 0.9596 0.6522 0.118 Uiso 1 1 calc R . . C10 C 0.9785(3) 1.0876(2) 0.8781(2) 0.0726(6) Uani 1 1 d . . . H10A H 1.0317 1.0224 0.8739 0.109 Uiso 1 1 calc R . . H10B H 0.9212 1.1087 0.9402 0.109 Uiso 1 1 calc R . . H10C H 1.0578 1.1598 0.8988 0.109 Uiso 1 1 calc R . . C11 C 0.4408(2) 0.80726(17) 0.57805(16) 0.0511(5) Uani 1 1 d . . . H11A H 0.4705 0.7296 0.5260 0.061 Uiso 1 1 calc R . . C12 C 0.3975(2) 0.79770(19) 0.68332(18) 0.0549(5) Uani 1 1 d . . . C13 C 0.3564(3) 0.8945(2) 0.7772(2) 0.0692(6) Uani 1 1 d . . . H13A H 0.3567 0.9693 0.7771 0.083 Uiso 1 1 calc R . . C14 C 0.3149(3) 0.8812(3) 0.8711(3) 0.0894(8) Uani 1 1 d . . . H14A H 0.2895 0.9475 0.9345 0.107 Uiso 1 1 calc R . . C15 C 0.3111(3) 0.7709(4) 0.8709(3) 0.1025(10) Uani 1 1 d . . . H15A H 0.2819 0.7618 0.9335 0.123 Uiso 1 1 calc R . . C16 C 0.3502(3) 0.6744(3) 0.7789(3) 0.1000(10) Uani 1 1 d . . . H16A H 0.3475 0.5995 0.7791 0.120 Uiso 1 1 calc R . . C17 C 0.3941(3) 0.6868(2) 0.6850(3) 0.0770(7) Uani 1 1 d . . . H17A H 0.4213 0.6204 0.6229 0.092 Uiso 1 1 calc R . . C18 C 0.3011(3) 0.8233(2) 0.49688(19) 0.0666(6) Uani 1 1 d . . . H18A H 0.2100 0.7545 0.4642 0.100 Uiso 1 1 calc R . . H18B H 0.3343 0.8257 0.4299 0.100 Uiso 1 1 calc R . . H18C H 0.2709 0.8997 0.5453 0.100 Uiso 1 1 calc R . . C19 C 0.6515(2) 1.71238(15) 1.19006(15) 0.0421(4) Uani 1 1 d . . . C20 C 0.7512(2) 1.64433(18) 1.21924(17) 0.0541(5) Uani 1 1 d . . . H20A H 0.7847 1.6619 1.3007 0.065 Uiso 1 1 calc R . . C21 C 0.8014(3) 1.55129(19) 1.12967(19) 0.0592(5) Uani 1 1 d . . . H21A H 0.8683 1.5059 1.1498 0.071 Uiso 1 1 calc R . . C22 C 0.7506(2) 1.52708(16) 1.01062(17) 0.0526(5) Uani 1 1 d . . . C23 C 0.6543(2) 1.59304(18) 0.97796(17) 0.0568(5) Uani 1 1 d . . . H23A H 0.6227 1.5756 0.8964 0.068 Uiso 1 1 calc R . . C24 C 0.6045(2) 1.68676(17) 1.06929(16) 0.0507(5) Uani 1 1 d . . . H24A H 0.5390 1.7326 1.0488 0.061 Uiso 1 1 calc R . . C25 C 0.5955(2) 1.81321(16) 1.28968(16) 0.0469(4) 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 O1 0.0812(10) 0.0609(9) 0.0645(9) 0.0262(7) 0.0288(7) 0.0392(8) O2 0.0911(11) 0.0845(10) 0.0444(8) 0.0267(7) 0.0298(7) 0.0382(9) O3 0.1553(19) 0.0823(13) 0.0718(12) 0.0147(10) 0.0625(12) 0.0325(12) O4 0.1075(14) 0.0569(10) 0.1257(15) 0.0299(10) 0.0600(12) 0.0383(10) N1 0.0473(8) 0.0442(8) 0.0413(8) 0.0206(6) 0.0172(6) 0.0176(7) N2 0.0817(13) 0.0491(11) 0.0783(14) 0.0158(10) 0.0439(11) 0.0108(10) C1 0.0449(10) 0.0443(10) 0.0374(9) 0.0177(7) 0.0137(7) 0.0157(8) C2 0.0429(10) 0.0442(10) 0.0472(10) 0.0207(8) 0.0108(8) 0.0119(8) C3 0.0805(15) 0.0630(13) 0.0545(12) 0.0255(10) 0.0237(10) 0.0364(11) C4 0.1030(19) 0.0673(15) 0.0772(16) 0.0204(13) 0.0278(14) 0.0459(14) C5 0.0915(18) 0.0607(15) 0.109(2) 0.0430(15) 0.0183(15) 0.0346(13) C6 0.0781(15) 0.0740(16) 0.0948(18) 0.0564(15) 0.0177(13) 0.0275(13) C7 0.0599(12) 0.0590(12) 0.0597(12) 0.0337(10) 0.0156(9) 0.0178(10) C8 0.0523(11) 0.0458(10) 0.0601(12) 0.0244(9) 0.0119(9) 0.0120(9) C9 0.0654(14) 0.0919(17) 0.0809(15) 0.0480(14) 0.0221(12) -0.0003(12) C10 0.0634(13) 0.0631(13) 0.0659(13) 0.0197(11) 0.0034(11) 0.0029(11) C11 0.0509(11) 0.0456(10) 0.0501(10) 0.0190(8) 0.0123(8) 0.0109(8) C12 0.0414(10) 0.0621(12) 0.0677(12) 0.0393(10) 0.0113(9) 0.0091(9) C13 0.0720(14) 0.0862(16) 0.0752(14) 0.0524(13) 0.0351(12) 0.0299(12) C14 0.0805(17) 0.136(2) 0.0917(18) 0.0757(18) 0.0454(14) 0.0433(17) C15 0.0698(17) 0.172(3) 0.135(3) 0.123(3) 0.0434(17) 0.0393(19) C16 0.0743(17) 0.121(2) 0.160(3) 0.113(2) 0.0352(18) 0.0199(17) C17 0.0612(14) 0.0729(15) 0.1070(19) 0.0560(14) 0.0185(13) 0.0077(11) C18 0.0559(12) 0.0791(15) 0.0557(12) 0.0311(11) 0.0052(9) 0.0104(11) C19 0.0436(9) 0.0376(9) 0.0443(9) 0.0183(8) 0.0171(7) 0.0070(7) C20 0.0645(12) 0.0554(11) 0.0518(11) 0.0293(9) 0.0240(9) 0.0231(10) C21 0.0662(13) 0.0540(12) 0.0707(13) 0.0343(10) 0.0311(10) 0.0263(10) C22 0.0562(11) 0.0367(10) 0.0601(12) 0.0153(9) 0.0306(9) 0.0088(8) C23 0.0628(12) 0.0563(12) 0.0421(10) 0.0167(9) 0.0198(9) 0.0070(10) C24 0.0548(11) 0.0513(11) 0.0470(10) 0.0238(9) 0.0163(8) 0.0151(9) C25 0.0499(10) 0.0440(10) 0.0467(11) 0.0194(8) 0.0207(8) 0.0119(8) _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 O1 C25 1.245(2) . ? O2 C25 1.237(2) . ? O3 N2 1.212(3) . ? O4 N2 1.224(3) . ? N1 C1 1.504(2) . ? N1 C11 1.511(2) . ? N2 C22 1.473(2) . ? C1 C2 1.514(2) . ? C1 C8 1.541(3) . ? C2 C3 1.380(3) . ? C2 C7 1.384(3) . ? C3 C4 1.389(3) . ? C4 C5 1.366(4) . ? C5 C6 1.363(3) . ? C6 C7 1.378(3) . ? C8 C9 1.523(3) . ? C8 C10 1.526(3) . ? C11 C12 1.507(3) . ? C11 C18 1.525(3) . ? C12 C13 1.384(3) . ? C12 C17 1.387(3) . ? C13 C14 1.383(3) . ? C14 C15 1.368(4) . ? C15 C16 1.361(4) . ? C16 C17 1.387(4) . ? C19 C24 1.378(2) . ? C19 C20 1.386(2) . ? C19 C25 1.515(2) . ? C20 C21 1.376(3) . ? C21 C22 1.365(3) . ? C22 C23 1.367(3) . ? C23 C24 1.389(3) . ? 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 C1 N1 C11 117.31(13) . . ? O3 N2 O4 124.2(2) . . ? O3 N2 C22 117.9(2) . . ? O4 N2 C22 117.9(2) . . ? N1 C1 C2 112.87(13) . . ? N1 C1 C8 109.41(14) . . ? C2 C1 C8 115.29(14) . . ? C3 C2 C7 118.10(17) . . ? C3 C2 C1 122.89(16) . . ? C7 C2 C1 119.01(16) . . ? C2 C3 C4 120.2(2) . . ? C5 C4 C3 120.3(2) . . ? C6 C5 C4 120.4(2) . . ? C5 C6 C7 119.4(2) . . ? C6 C7 C2 121.5(2) . . ? C9 C8 C10 110.03(18) . . ? C9 C8 C1 115.05(16) . . ? C10 C8 C1 109.71(16) . . ? C12 C11 N1 112.56(14) . . ? C12 C11 C18 113.22(16) . . ? N1 C11 C18 107.66(15) . . ? C13 C12 C17 118.4(2) . . ? C13 C12 C11 122.51(18) . . ? C17 C12 C11 119.07(19) . . ? C14 C13 C12 120.7(2) . . ? C15 C14 C13 120.1(3) . . ? C16 C15 C14 120.0(3) . . ? C15 C16 C17 120.6(3) . . ? C12 C17 C16 120.2(3) . . ? C24 C19 C20 118.88(16) . . ? C24 C19 C25 120.80(16) . . ? C20 C19 C25 120.32(16) . . ? C21 C20 C19 121.11(18) . . ? C22 C21 C20 118.47(18) . . ? C21 C22 C23 122.41(17) . . ? C21 C22 N2 118.50(19) . . ? C23 C22 N2 119.09(19) . . ? C22 C23 C24 118.53(17) . . ? C19 C24 C23 120.58(18) . . ? O2 C25 O1 126.29(16) . . ? O2 C25 C19 117.08(16) . . ? O1 C25 C19 116.62(16) . . ? 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 C11 N1 C1 C2 49.56(19) . . . . ? C11 N1 C1 C8 179.37(14) . . . . ? N1 C1 C2 C3 47.8(2) . . . . ? C8 C1 C2 C3 -78.9(2) . . . . ? N1 C1 C2 C7 -132.66(17) . . . . ? C8 C1 C2 C7 100.6(2) . . . . ? C7 C2 C3 C4 0.2(3) . . . . ? C1 C2 C3 C4 179.7(2) . . . . ? C2 C3 C4 C5 -0.3(4) . . . . ? C3 C4 C5 C6 -0.3(4) . . . . ? C4 C5 C6 C7 1.0(4) . . . . ? C5 C6 C7 C2 -1.2(3) . . . . ? C3 C2 C7 C6 0.6(3) . . . . ? C1 C2 C7 C6 -178.96(19) . . . . ? N1 C1 C8 C9 -72.5(2) . . . . ? C2 C1 C8 C9 56.0(2) . . . . ? N1 C1 C8 C10 162.79(15) . . . . ? C2 C1 C8 C10 -68.7(2) . . . . ? C1 N1 C11 C12 43.1(2) . . . . ? C1 N1 C11 C18 168.61(14) . . . . ? N1 C11 C12 C13 58.6(2) . . . . ? C18 C11 C12 C13 -63.8(2) . . . . ? N1 C11 C12 C17 -123.31(19) . . . . ? C18 C11 C12 C17 114.3(2) . . . . ? C17 C12 C13 C14 0.8(3) . . . . ? C11 C12 C13 C14 178.9(2) . . . . ? C12 C13 C14 C15 -1.2(4) . . . . ? C13 C14 C15 C16 0.8(4) . . . . ? C14 C15 C16 C17 0.0(4) . . . . ? C13 C12 C17 C16 0.0(3) . . . . ? C11 C12 C17 C16 -178.2(2) . . . . ? C15 C16 C17 C12 -0.4(4) . . . . ? C24 C19 C20 C21 -0.9(3) . . . . ? C25 C19 C20 C21 179.12(17) . . . . ? C19 C20 C21 C22 0.0(3) . . . . ? C20 C21 C22 C23 1.0(3) . . . . ? C20 C21 C22 N2 -178.50(17) . . . . ? O3 N2 C22 C21 -173.2(2) . . . . ? O4 N2 C22 C21 5.7(3) . . . . ? O3 N2 C22 C23 7.3(3) . . . . ? O4 N2 C22 C23 -173.83(19) . . . . ? C21 C22 C23 C24 -1.0(3) . . . . ? N2 C22 C23 C24 178.53(16) . . . . ? C20 C19 C24 C23 1.0(3) . . . . ? C25 C19 C24 C23 -179.09(16) . . . . ? C22 C23 C24 C19 0.0(3) . . . . ? C24 C19 C25 O2 -178.06(17) . . . . ? C20 C19 C25 O2 1.9(3) . . . . ? C24 C19 C25 O1 1.6(3) . . . . ? C20 C19 C25 O1 -178.48(17) . . . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.158 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.031 #===END