# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Paul Evans' 'Johannes E. M. N. Klein' 'Helge Muller-Bunz' _publ_contact_author_name 'Paul Evans' _publ_contact_author_email PAUL.EVANS@UCD.IE _publ_section_title ; Studies Concerning the Electrophile Amino-Alkene Cyclisation for the Synthesis of Bicyclic Amines ; # Attachment 'eva27.cif' data_eva27_50 _database_code_depnum_ccdc_archive 'CCDC 707945' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H19 N' _chemical_formula_weight 213.31 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' _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 5.8108(8) _cell_length_b 10.4031(15) _cell_length_c 10.8646(15) _cell_angle_alpha 68.858(3) _cell_angle_beta 87.535(3) _cell_angle_gamma 79.418(3) _cell_volume 601.95(15) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1912 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 24.96 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.177 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 232 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8286 _exptl_absorpt_correction_T_max 0.9966 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.162 before and 0.032 after correction. The Ratio of minimum to maximum transmission is 0.831396. The \l/2 correction factor is 0.0015 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6448 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.08 _reflns_number_total 2129 _reflns_number_gt 1777 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0432P)^2^+0.0961P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2129 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0461 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0934 _refine_ls_wR_factor_gt 0.0885 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.001 _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 N N 0.19827(18) 0.78698(10) 0.87661(10) 0.0192(3) Uani 1 1 d . . . C1 C 0.1525(2) 0.80143(13) 0.74014(12) 0.0192(3) Uani 1 1 d . . . H1 H 0.286(2) 0.8370(14) 0.6833(13) 0.020(3) Uiso 1 1 d . . . C2 C 0.1135(3) 0.67052(14) 0.71917(13) 0.0235(3) Uani 1 1 d . . . H2A H -0.009(3) 0.6297(15) 0.7830(14) 0.030(4) Uiso 1 1 d . . . H2B H 0.260(3) 0.5995(15) 0.7366(13) 0.025(4) Uiso 1 1 d . . . C3 C 0.0248(2) 0.71358(15) 0.57715(14) 0.0245(3) Uani 1 1 d . . . H3A H 0.141(2) 0.7603(14) 0.5180(13) 0.021(3) Uiso 1 1 d . . . H3B H 0.010(3) 0.6318(16) 0.5550(14) 0.032(4) Uiso 1 1 d . . . C4 C -0.2088(2) 0.81518(15) 0.54986(14) 0.0254(3) Uani 1 1 d . . . H4A H -0.238(2) 0.8652(15) 0.4519(15) 0.029(4) Uiso 1 1 d . . . H4B H -0.336(3) 0.7605(15) 0.5800(14) 0.031(4) Uiso 1 1 d . . . C5 C -0.2255(2) 0.91981(14) 0.61715(13) 0.0218(3) Uani 1 1 d . . . H5 H -0.370(3) 0.9946(15) 0.5978(13) 0.025(4) Uiso 1 1 d . . . C6 C -0.0636(2) 0.91371(13) 0.70237(12) 0.0187(3) Uani 1 1 d . . . C7 C -0.0662(2) 1.00025(14) 0.78824(14) 0.0225(3) Uani 1 1 d . . . H7A H -0.207(3) 0.9926(14) 0.8433(13) 0.024(4) Uiso 1 1 d . . . H7B H -0.071(2) 1.1001(16) 0.7358(14) 0.028(4) Uiso 1 1 d . . . C8 C 0.1592(2) 0.93225(13) 0.87150(14) 0.0225(3) Uani 1 1 d . . . H8A H 0.298(2) 0.9808(14) 0.8260(13) 0.024(4) Uiso 1 1 d . . . H8B H 0.150(2) 0.9343(14) 0.9616(14) 0.025(4) Uiso 1 1 d . . . C9 C 0.4336(2) 0.71065(14) 0.92644(13) 0.0217(3) Uani 1 1 d . . . H9A H 0.557(2) 0.7623(14) 0.8750(13) 0.023(3) Uiso 1 1 d . . . H9B H 0.458(2) 0.6184(15) 0.9135(13) 0.024(3) Uiso 1 1 d . . . C10 C 0.4665(2) 0.68772(13) 1.07033(12) 0.0194(3) Uani 1 1 d . . . C11 C 0.3081(2) 0.62578(13) 1.16258(13) 0.0217(3) Uani 1 1 d . . . H11 H 0.177(3) 0.5972(14) 1.1317(13) 0.025(4) Uiso 1 1 d . . . C12 C 0.3359(2) 0.60485(14) 1.29459(13) 0.0237(3) Uani 1 1 d . . . H12 H 0.220(3) 0.5608(14) 1.3573(14) 0.026(4) Uiso 1 1 d . . . C13 C 0.5225(2) 0.64538(13) 1.33714(13) 0.0239(3) Uani 1 1 d . . . H13 H 0.541(2) 0.6327(15) 1.4290(15) 0.029(4) Uiso 1 1 d . . . C14 C 0.6819(2) 0.70573(14) 1.24683(14) 0.0251(3) Uani 1 1 d . . . H14 H 0.815(3) 0.7336(15) 1.2774(14) 0.031(4) Uiso 1 1 d . . . C15 C 0.6547(2) 0.72703(13) 1.11429(13) 0.0229(3) Uani 1 1 d . . . H15 H 0.769(3) 0.7692(15) 1.0501(14) 0.030(4) Uiso 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 N 0.0185(6) 0.0213(6) 0.0173(6) -0.0078(5) -0.0008(4) 0.0002(4) C1 0.0177(7) 0.0220(7) 0.0168(7) -0.0063(5) 0.0033(5) -0.0034(5) C2 0.0245(8) 0.0226(7) 0.0231(8) -0.0092(6) 0.0005(6) -0.0013(6) C3 0.0246(8) 0.0269(7) 0.0256(8) -0.0138(6) 0.0020(6) -0.0046(6) C4 0.0216(8) 0.0335(8) 0.0240(8) -0.0133(6) 0.0003(6) -0.0058(6) C5 0.0170(7) 0.0258(7) 0.0203(7) -0.0067(6) 0.0022(6) -0.0018(6) C6 0.0195(7) 0.0183(6) 0.0167(7) -0.0044(5) 0.0043(5) -0.0043(5) C7 0.0213(8) 0.0223(7) 0.0224(7) -0.0080(6) 0.0004(6) 0.0000(6) C8 0.0231(8) 0.0239(7) 0.0216(8) -0.0108(6) -0.0016(6) -0.0005(6) C9 0.0186(7) 0.0227(7) 0.0208(7) -0.0066(6) 0.0009(6) 0.0010(6) C10 0.0177(7) 0.0169(6) 0.0199(7) -0.0047(5) -0.0002(5) 0.0020(5) C11 0.0166(7) 0.0219(7) 0.0253(7) -0.0079(6) -0.0016(6) -0.0009(5) C12 0.0207(7) 0.0250(7) 0.0216(8) -0.0055(6) 0.0040(6) -0.0020(6) C13 0.0283(8) 0.0224(7) 0.0186(8) -0.0080(6) -0.0026(6) 0.0034(6) C14 0.0239(8) 0.0228(7) 0.0283(8) -0.0089(6) -0.0064(6) -0.0026(6) C15 0.0195(7) 0.0207(7) 0.0251(8) -0.0046(6) 0.0011(6) -0.0027(6) _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 N C9 1.4655(17) . ? N C1 1.4664(16) . ? N C8 1.4674(16) . ? C1 C6 1.5063(18) . ? C1 C2 1.5163(18) . ? C1 H1 1.009(14) . ? C2 C3 1.5272(19) . ? C2 H2A 1.012(15) . ? C2 H2B 0.994(15) . ? C3 C4 1.526(2) . ? C3 H3A 0.981(14) . ? C3 H3B 0.981(15) . ? C4 C5 1.5026(18) . ? C4 H4A 1.008(15) . ? C4 H4B 0.988(15) . ? C5 C6 1.3256(18) . ? C5 H5 1.007(15) . ? C6 C7 1.5103(18) . ? C7 C8 1.5282(19) . ? C7 H7A 0.990(14) . ? C7 H7B 0.984(15) . ? C8 H8A 1.040(14) . ? C8 H8B 0.986(14) . ? C9 C10 1.5091(18) . ? C9 H9A 1.002(14) . ? C9 H9B 1.003(14) . ? C10 C11 1.3927(18) . ? C10 C15 1.3937(18) . ? C11 C12 1.3829(19) . ? C11 H11 0.977(14) . ? C12 C13 1.3853(19) . ? C12 H12 0.987(14) . ? C13 C14 1.380(2) . ? C13 H13 0.967(15) . ? C14 C15 1.3871(19) . ? C14 H14 0.982(15) . ? C15 H15 0.982(15) . ? 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 C9 N C1 113.27(10) . . ? C9 N C8 112.57(10) . . ? C1 N C8 103.61(10) . . ? N C1 C6 102.14(10) . . ? N C1 C2 116.34(10) . . ? C6 C1 C2 111.20(11) . . ? N C1 H1 109.5(7) . . ? C6 C1 H1 109.3(8) . . ? C2 C1 H1 108.1(7) . . ? C1 C2 C3 107.84(11) . . ? C1 C2 H2A 107.9(8) . . ? C3 C2 H2A 110.1(8) . . ? C1 C2 H2B 111.3(8) . . ? C3 C2 H2B 110.8(8) . . ? H2A C2 H2B 108.8(11) . . ? C4 C3 C2 112.18(11) . . ? C4 C3 H3A 108.3(8) . . ? C2 C3 H3A 108.2(8) . . ? C4 C3 H3B 109.6(9) . . ? C2 C3 H3B 111.6(9) . . ? H3A C3 H3B 106.8(11) . . ? C5 C4 C3 113.00(11) . . ? C5 C4 H4A 110.1(8) . . ? C3 C4 H4A 110.4(8) . . ? C5 C4 H4B 109.4(8) . . ? C3 C4 H4B 108.5(9) . . ? H4A C4 H4B 105.1(11) . . ? C6 C5 C4 122.77(13) . . ? C6 C5 H5 120.1(7) . . ? C4 C5 H5 117.1(7) . . ? C5 C6 C1 122.95(12) . . ? C5 C6 C7 129.17(12) . . ? C1 C6 C7 107.57(11) . . ? C6 C7 C8 102.85(11) . . ? C6 C7 H7A 109.5(8) . . ? C8 C7 H7A 111.9(8) . . ? C6 C7 H7B 112.1(8) . . ? C8 C7 H7B 112.9(8) . . ? H7A C7 H7B 107.6(11) . . ? N C8 C7 103.62(10) . . ? N C8 H8A 110.5(7) . . ? C7 C8 H8A 110.6(7) . . ? N C8 H8B 110.1(8) . . ? C7 C8 H8B 114.4(8) . . ? H8A C8 H8B 107.6(11) . . ? N C9 C10 111.53(10) . . ? N C9 H9A 111.1(8) . . ? C10 C9 H9A 108.6(7) . . ? N C9 H9B 108.3(8) . . ? C10 C9 H9B 110.3(8) . . ? H9A C9 H9B 106.9(11) . . ? C11 C10 C15 118.48(12) . . ? C11 C10 C9 120.25(12) . . ? C15 C10 C9 121.27(12) . . ? C12 C11 C10 120.74(12) . . ? C12 C11 H11 121.0(8) . . ? C10 C11 H11 118.3(8) . . ? C11 C12 C13 120.34(13) . . ? C11 C12 H12 118.6(8) . . ? C13 C12 H12 121.0(8) . . ? C14 C13 C12 119.45(13) . . ? C14 C13 H13 119.7(9) . . ? C12 C13 H13 120.8(9) . . ? C13 C14 C15 120.45(13) . . ? C13 C14 H14 119.2(8) . . ? C15 C14 H14 120.3(9) . . ? C14 C15 C10 120.53(13) . . ? C14 C15 H15 120.5(8) . . ? C10 C15 H15 118.9(8) . . ? 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 C9 N C1 C6 -164.91(10) . . . . ? C8 N C1 C6 -42.64(12) . . . . ? C9 N C1 C2 73.81(14) . . . . ? C8 N C1 C2 -163.92(11) . . . . ? N C1 C2 C3 169.61(11) . . . . ? C6 C1 C2 C3 53.27(15) . . . . ? C1 C2 C3 C4 -61.87(15) . . . . ? C2 C3 C4 C5 38.20(16) . . . . ? C3 C4 C5 C6 -6.87(19) . . . . ? C4 C5 C6 C1 -0.1(2) . . . . ? C4 C5 C6 C7 -172.87(13) . . . . ? N C1 C6 C5 -149.06(12) . . . . ? C2 C1 C6 C5 -24.30(17) . . . . ? N C1 C6 C7 25.08(13) . . . . ? C2 C1 C6 C7 149.85(11) . . . . ? C5 C6 C7 C8 174.84(13) . . . . ? C1 C6 C7 C8 1.18(14) . . . . ? C9 N C8 C7 166.98(11) . . . . ? C1 N C8 C7 44.24(13) . . . . ? C6 C7 C8 N -27.17(13) . . . . ? C1 N C9 C10 -175.28(10) . . . . ? C8 N C9 C10 67.58(14) . . . . ? N C9 C10 C11 53.12(16) . . . . ? N C9 C10 C15 -127.14(13) . . . . ? C15 C10 C11 C12 0.54(19) . . . . ? C9 C10 C11 C12 -179.70(12) . . . . ? C10 C11 C12 C13 0.0(2) . . . . ? C11 C12 C13 C14 -0.6(2) . . . . ? C12 C13 C14 C15 0.6(2) . . . . ? C13 C14 C15 C10 -0.1(2) . . . . ? C11 C10 C15 C14 -0.51(19) . . . . ? C9 C10 C15 C14 179.73(12) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.08 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.257 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.038 # Attachment 'eva30.cif' data_eva30 _database_code_depnum_ccdc_archive 'CCDC 707946' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H24 N O, Br' _chemical_formula_sum 'C16 H24 N O Br' _chemical_formula_weight 326.27 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.078(7) _cell_length_b 4.8656(12) _cell_length_c 22.535(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.268(5) _cell_angle_gamma 90.00 _cell_volume 3169.3(13) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5761 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 28.94 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 2.588 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6831 _exptl_absorpt_correction_T_max 0.8815 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.067 before and 0.027 after correction. The Ratio of minimum to maximum transmission is 0.774880. The \l/2 correction factor is 0.0015 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32279 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 29.12 _reflns_number_total 4257 _reflns_number_gt 3860 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0379P)^2^+2.1097P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4257 _refine_ls_number_parameters 270 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0255 _refine_ls_wR_factor_ref 0.0645 _refine_ls_wR_factor_gt 0.0626 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.002 _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 1.08903(4) 0.7478(3) 0.15468(6) 0.0144(2) Uani 1 1 d . . . C2 C 1.10797(5) 0.9292(3) 0.11640(6) 0.0159(3) Uani 1 1 d . . . H2 H 1.0961(6) 0.932(4) 0.0758(8) 0.021(4) Uiso 1 1 d . . . C3 C 1.14388(5) 1.1071(3) 0.13680(6) 0.0167(3) Uani 1 1 d . . . H3 H 1.1559(6) 1.222(4) 0.1098(8) 0.024(5) Uiso 1 1 d . . . C4 C 1.16083(5) 1.1045(3) 0.19707(6) 0.0168(3) Uani 1 1 d . . . O O 1.19600(3) 1.2672(2) 0.22219(5) 0.0220(2) Uani 1 1 d . . . C7 C 1.21903(6) 1.4366(4) 0.18293(8) 0.0251(3) Uani 1 1 d . . . H7A H 1.2433(7) 1.532(5) 0.2090(9) 0.034(5) Uiso 1 1 d . . . H7B H 1.2335(7) 1.335(5) 0.1559(9) 0.030(5) Uiso 1 1 d . . . H7C H 1.1978(7) 1.566(4) 0.1640(9) 0.026(5) Uiso 1 1 d . . . C5 C 1.14177(5) 0.9255(3) 0.23605(6) 0.0203(3) Uani 1 1 d . . . H5 H 1.1540(6) 0.924(4) 0.2774(9) 0.026(5) Uiso 1 1 d . . . C6 C 1.10657(5) 0.7484(3) 0.21501(6) 0.0185(3) Uani 1 1 d . . . H6 H 1.0944(7) 0.627(4) 0.2398(9) 0.026(5) Uiso 1 1 d . . . C8 C 1.04940(5) 0.5625(3) 0.13310(6) 0.0153(2) Uani 1 1 d . . . H8A H 1.0515(6) 0.500(4) 0.0923(8) 0.021(5) Uiso 1 1 d . . . H8B H 1.0474(6) 0.411(4) 0.1606(8) 0.020(5) Uiso 1 1 d . . . N N 1.00432(4) 0.7172(2) 0.13049(5) 0.0127(2) Uani 1 1 d . . . H1N H 1.0025(6) 0.799(4) 0.1633(8) 0.023(5) Uiso 1 1 d . . . H2N H 1.0037(6) 0.842(4) 0.1033(8) 0.018(4) Uiso 1 1 d . . . C9 C 0.96278(5) 0.5406(3) 0.11450(6) 0.0149(2) Uani 1 1 d . . . H9A H 0.9665(6) 0.461(4) 0.0756(8) 0.020(4) Uiso 1 1 d . . . H9B H 0.9639(6) 0.397(4) 0.1446(8) 0.020(4) Uiso 1 1 d . . . C10 C 0.91859(5) 0.7108(3) 0.11252(6) 0.0163(3) Uani 1 1 d . . . H10A H 0.9145(6) 0.773(4) 0.1519(8) 0.021(4) Uiso 1 1 d . . . H10B H 0.9224(7) 0.873(4) 0.0877(8) 0.028(5) Uiso 1 1 d . . . C11 C 0.87728(5) 0.5440(3) 0.08703(6) 0.0153(2) Uani 1 1 d . . . C12 C 0.84574(5) 0.4522(4) 0.12076(7) 0.0241(3) Uani 1 1 d . . . H12 H 0.8482(7) 0.496(4) 0.1616(10) 0.032(5) Uiso 1 1 d . . . C13 C 0.80480(6) 0.2779(4) 0.09751(8) 0.0325(4) Uani 1 1 d . . . H13A H 0.7765(8) 0.388(5) 0.0949(10) 0.036(6) Uiso 1 1 d . . . H13B H 0.8030(8) 0.134(5) 0.1247(10) 0.047(6) Uiso 1 1 d . . . C14 C 0.80937(6) 0.1642(3) 0.03573(8) 0.0294(4) Uani 1 1 d . . . H14A H 0.7800(7) 0.089(5) 0.0192(9) 0.034(5) Uiso 1 1 d . . . H14B H 0.8310(8) 0.022(5) 0.0369(10) 0.045(7) Uiso 1 1 d . . . C15 C 0.82608(5) 0.3846(4) -0.00409(7) 0.0242(3) Uani 1 1 d . . . H15A H 0.8036(7) 0.537(4) -0.0063(9) 0.028(5) Uiso 1 1 d . . . H15B H 0.8255(7) 0.320(5) -0.0452(9) 0.030(5) Uiso 1 1 d . . . C16 C 0.87410(5) 0.4836(4) 0.02108(7) 0.0221(3) Uani 1 1 d . . . H16A H 0.8826(7) 0.646(5) -0.0002(9) 0.033(5) Uiso 1 1 d . . . H16B H 0.8970(7) 0.342(5) 0.0140(9) 0.033(5) Uiso 1 1 d . . . Br1 Br 1.0000 1.10483(4) 0.2500 0.01763(6) Uani 1 2 d S . . Br2 Br 1.0000 1.0000 0.0000 0.01936(6) Uani 1 2 d S . . 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 0.0127(5) 0.0146(6) 0.0159(6) -0.0008(5) 0.0014(5) 0.0013(5) C2 0.0167(6) 0.0180(6) 0.0128(6) 0.0004(5) 0.0008(5) 0.0004(5) C3 0.0169(6) 0.0157(6) 0.0173(6) 0.0018(5) 0.0012(5) -0.0012(5) C4 0.0146(6) 0.0163(6) 0.0187(6) -0.0006(5) -0.0011(5) 0.0002(5) O 0.0195(5) 0.0228(5) 0.0221(5) 0.0009(4) -0.0046(4) -0.0059(4) C7 0.0212(7) 0.0238(8) 0.0302(8) -0.0018(7) 0.0019(6) -0.0072(6) C5 0.0204(7) 0.0259(8) 0.0137(6) 0.0022(5) -0.0025(5) -0.0015(6) C6 0.0184(6) 0.0226(8) 0.0145(6) 0.0032(5) 0.0016(5) -0.0023(5) C8 0.0141(6) 0.0145(6) 0.0172(6) -0.0001(5) 0.0016(5) 0.0007(5) N 0.0144(5) 0.0129(5) 0.0107(5) -0.0002(4) 0.0006(4) -0.0012(4) C9 0.0141(6) 0.0144(6) 0.0155(6) 0.0002(5) -0.0007(5) -0.0023(5) C10 0.0148(6) 0.0161(6) 0.0177(6) -0.0025(5) 0.0006(5) -0.0007(5) C11 0.0138(6) 0.0162(6) 0.0154(6) -0.0006(5) -0.0014(5) 0.0015(5) C12 0.0209(7) 0.0311(8) 0.0202(7) 0.0013(6) 0.0022(6) -0.0055(6) C13 0.0231(8) 0.0400(10) 0.0339(9) 0.0109(8) 0.0006(7) -0.0126(7) C14 0.0208(7) 0.0179(7) 0.0460(10) -0.0006(7) -0.0118(7) -0.0013(6) C15 0.0188(7) 0.0304(9) 0.0220(7) -0.0077(6) -0.0045(5) 0.0021(6) C16 0.0175(7) 0.0316(9) 0.0170(7) -0.0049(6) -0.0001(5) -0.0016(6) Br1 0.02543(10) 0.01682(10) 0.01085(9) 0.000 0.00290(7) 0.000 Br2 0.02650(11) 0.02047(11) 0.01102(9) 0.00310(7) 0.00157(7) 0.00151(7) _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 1.3894(19) . ? C1 C6 1.3989(18) . ? C1 C8 1.5016(19) . ? C2 C3 1.3951(19) . ? C2 H2 0.942(18) . ? C3 C4 1.3934(19) . ? C3 H3 0.922(19) . ? C4 O 1.3660(17) . ? C4 C5 1.394(2) . ? O C7 1.4284(19) . ? C7 H7A 0.98(2) . ? C7 H7B 0.92(2) . ? C7 H7C 0.95(2) . ? C5 C6 1.382(2) . ? C5 H5 0.960(19) . ? C6 H6 0.91(2) . ? C8 N 1.5072(17) . ? C8 H8A 0.976(19) . ? C8 H8B 0.971(19) . ? N C9 1.4936(17) . ? N H1N 0.845(19) . ? N H2N 0.862(19) . ? C9 C10 1.5254(19) . ? C9 H9A 0.976(19) . ? C9 H9B 0.973(19) . ? C10 C11 1.5105(19) . ? C10 H10A 0.956(18) . ? C10 H10B 0.98(2) . ? C11 C12 1.331(2) . ? C11 C16 1.508(2) . ? C12 C13 1.508(2) . ? C12 H12 0.94(2) . ? C13 C14 1.517(3) . ? C13 H13A 0.98(2) . ? C13 H13B 0.93(2) . ? C14 C15 1.512(2) . ? C14 H14A 0.97(2) . ? C14 H14B 0.93(2) . ? C15 C16 1.526(2) . ? C15 H15A 0.99(2) . ? C15 H15B 0.98(2) . ? C16 H16A 0.97(2) . ? C16 H16B 0.98(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 C2 C1 C6 118.36(13) . . ? C2 C1 C8 121.50(12) . . ? C6 C1 C8 120.09(12) . . ? C1 C2 C3 121.52(13) . . ? C1 C2 H2 119.0(12) . . ? C3 C2 H2 119.5(12) . . ? C4 C3 C2 119.21(13) . . ? C4 C3 H3 122.0(11) . . ? C2 C3 H3 118.8(11) . . ? O C4 C3 124.60(13) . . ? O C4 C5 115.59(12) . . ? C3 C4 C5 119.81(13) . . ? C4 O C7 117.26(11) . . ? O C7 H7A 104.8(12) . . ? O C7 H7B 112.3(14) . . ? H7A C7 H7B 107.3(18) . . ? O C7 H7C 109.6(12) . . ? H7A C7 H7C 110.2(18) . . ? H7B C7 H7C 112.4(17) . . ? C6 C5 C4 120.26(13) . . ? C6 C5 H5 120.6(12) . . ? C4 C5 H5 119.1(12) . . ? C5 C6 C1 120.84(13) . . ? C5 C6 H6 121.1(12) . . ? C1 C6 H6 118.0(12) . . ? C1 C8 N 110.26(11) . . ? C1 C8 H8A 111.5(11) . . ? N C8 H8A 105.2(11) . . ? C1 C8 H8B 110.4(11) . . ? N C8 H8B 107.0(11) . . ? H8A C8 H8B 112.2(16) . . ? C9 N C8 113.54(11) . . ? C9 N H1N 110.7(13) . . ? C8 N H1N 109.7(13) . . ? C9 N H2N 106.3(12) . . ? C8 N H2N 109.2(12) . . ? H1N N H2N 107.1(19) . . ? N C9 C10 110.58(11) . . ? N C9 H9A 106.1(11) . . ? C10 C9 H9A 111.5(11) . . ? N C9 H9B 106.2(11) . . ? C10 C9 H9B 112.1(11) . . ? H9A C9 H9B 110.0(15) . . ? C11 C10 C9 110.60(12) . . ? C11 C10 H10A 110.4(11) . . ? C9 C10 H10A 109.4(11) . . ? C11 C10 H10B 110.5(11) . . ? C9 C10 H10B 107.9(11) . . ? H10A C10 H10B 108.0(16) . . ? C12 C11 C16 121.74(13) . . ? C12 C11 C10 122.14(13) . . ? C16 C11 C10 116.12(12) . . ? C11 C12 C13 123.86(15) . . ? C11 C12 H12 120.0(13) . . ? C13 C12 H12 116.1(13) . . ? C12 C13 C14 112.26(14) . . ? C12 C13 H13A 110.0(13) . . ? C14 C13 H13A 107.6(13) . . ? C12 C13 H13B 106.9(14) . . ? C14 C13 H13B 110.3(14) . . ? H13A C13 H13B 109.9(19) . . ? C15 C14 C13 110.60(14) . . ? C15 C14 H14A 111.6(13) . . ? C13 C14 H14A 109.3(12) . . ? C15 C14 H14B 106.6(15) . . ? C13 C14 H14B 111.7(14) . . ? H14A C14 H14B 107.0(19) . . ? C14 C15 C16 110.08(13) . . ? C14 C15 H15A 108.1(11) . . ? C16 C15 H15A 110.7(12) . . ? C14 C15 H15B 111.3(13) . . ? C16 C15 H15B 112.0(11) . . ? H15A C15 H15B 104.5(16) . . ? C11 C16 C15 112.51(13) . . ? C11 C16 H16A 109.8(12) . . ? C15 C16 H16A 110.1(12) . . ? C11 C16 H16B 109.0(12) . . ? C15 C16 H16B 109.2(13) . . ? H16A C16 H16B 106.0(17) . . ? 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 C6 C1 C2 C3 0.5(2) . . . . ? C8 C1 C2 C3 178.08(13) . . . . ? C1 C2 C3 C4 -0.6(2) . . . . ? C2 C3 C4 O 179.51(13) . . . . ? C2 C3 C4 C5 -0.1(2) . . . . ? C3 C4 O C7 -4.8(2) . . . . ? C5 C4 O C7 174.86(14) . . . . ? O C4 C5 C6 -178.81(13) . . . . ? C3 C4 C5 C6 0.8(2) . . . . ? C4 C5 C6 C1 -0.9(2) . . . . ? C2 C1 C6 C5 0.2(2) . . . . ? C8 C1 C6 C5 -177.37(13) . . . . ? C2 C1 C8 N -81.38(15) . . . . ? C6 C1 C8 N 96.14(15) . . . . ? C1 C8 N C9 -174.96(11) . . . . ? C8 N C9 C10 -179.81(11) . . . . ? N C9 C10 C11 171.05(11) . . . . ? C9 C10 C11 C12 108.01(16) . . . . ? C9 C10 C11 C16 -71.19(16) . . . . ? C16 C11 C12 C13 1.1(3) . . . . ? C10 C11 C12 C13 -178.08(15) . . . . ? C11 C12 C13 C14 13.3(3) . . . . ? C12 C13 C14 C15 -44.4(2) . . . . ? C13 C14 C15 C16 62.31(17) . . . . ? C12 C11 C16 C15 16.2(2) . . . . ? C10 C11 C16 C15 -164.56(13) . . . . ? C14 C15 C16 C11 -47.23(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N H1N Br1 0.845(19) 2.46(2) 3.3016(13) 170.6(18) . N H2N Br2 0.862(19) 2.442(19) 3.2368(13) 153.6(16) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 29.12 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.713 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.079 # Attachment 'eva32.cif' data_eva32 _database_code_depnum_ccdc_archive 'CCDC 707947' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H21 N Br, Cl' _chemical_formula_sum 'C15 H21 N Cl Br' _chemical_formula_weight 330.69 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.387(5) _cell_length_b 6.8937(12) _cell_length_c 19.161(3) _cell_angle_alpha 90.00 _cell_angle_beta 122.455(3) _cell_angle_gamma 90.00 _cell_volume 2941.0(9) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5712 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 28.18 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 2.960 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4412 _exptl_absorpt_correction_T_max 0.5890 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.057 before and 0.024 after correction. The Ratio of minimum to maximum transmission is 0.749134. The \l/2 correction factor is 0.0015 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28702 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0157 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 28.25 _reflns_number_total 3626 _reflns_number_gt 3328 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0434P)^2^+2.3498P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3626 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0267 _refine_ls_wR_factor_ref 0.0700 _refine_ls_wR_factor_gt 0.0686 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.001 _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 0.14225(6) 1.0005(2) 0.56082(9) 0.0138(3) Uani 1 1 d . . . H1 H 0.1433 1.1441 0.5690 0.017 Uiso 1 1 calc R . . C2 C 0.11094(7) 0.9077(2) 0.60005(10) 0.0169(3) Uani 1 1 d . . . H2A H 0.0750 0.9855 0.5852 0.020 Uiso 1 1 calc R . . H2B H 0.1384 0.9124 0.6609 0.020 Uiso 1 1 calc R . . C3 C 0.09167(7) 0.6971(2) 0.57392(10) 0.0189(3) Uani 1 1 d . . . H3A H 0.1277 0.6132 0.5985 0.023 Uiso 1 1 calc R . . H3B H 0.0666 0.6533 0.5951 0.023 Uiso 1 1 calc R . . C4 C 0.05611(8) 0.6770(2) 0.47994(11) 0.0211(3) Uani 1 1 d . . . H4A H 0.0453 0.5392 0.4646 0.025 Uiso 1 1 calc R . . H4B H 0.0185 0.7527 0.4556 0.025 Uiso 1 1 calc R . . C5 C 0.09290(7) 0.7495(2) 0.44520(9) 0.0193(3) Uani 1 1 d . . . H5A H 0.0686 0.7371 0.3842 0.023 Uiso 1 1 calc R . . H5B H 0.1289 0.6664 0.4664 0.023 Uiso 1 1 calc R . . C6 C 0.11287(7) 0.9602(2) 0.46800(9) 0.0167(3) Uani 1 1 d . . . Br Br 0.041304(7) 1.12807(2) 0.406496(10) 0.02282(7) Uani 1 1 d . . . C7 C 0.16091(7) 1.0221(3) 0.45052(10) 0.0234(3) Uani 1 1 d . . . H7A H 0.1554 1.1595 0.4328 0.028 Uiso 1 1 calc R . . H7B H 0.1589 0.9404 0.4066 0.028 Uiso 1 1 calc R . . C8 C 0.22117(7) 0.9940(2) 0.53271(9) 0.0148(3) Uani 1 1 d . . . H8A H 0.2455 0.8939 0.5269 0.018 Uiso 1 1 calc R . . H8B H 0.2441 1.1170 0.5504 0.018 Uiso 1 1 calc R . . N N 0.20613(6) 0.93041(19) 0.59534(8) 0.0124(2) Uani 1 1 d . . . H1N H 0.2078(9) 0.801(3) 0.5967(12) 0.020(5) Uiso 1 1 d . . . C9 C 0.24942(7) 1.0053(2) 0.68178(9) 0.0148(3) Uani 1 1 d . . . H9A H 0.2416 1.1450 0.6837 0.018 Uiso 1 1 calc R . . H9B H 0.2418 0.9369 0.7207 0.018 Uiso 1 1 calc R . . C10 C 0.31464(7) 0.9791(2) 0.71035(9) 0.0154(3) Uani 1 1 d . . . C11 C 0.34685(8) 1.1365(2) 0.70750(10) 0.0197(3) Uani 1 1 d . . . H11 H 0.3272 1.2573 0.6859 0.024 Uiso 1 1 calc R . . C12 C 0.40763(8) 1.1172(3) 0.73628(11) 0.0252(4) Uani 1 1 d . . . H12 H 0.4292 1.2242 0.7337 0.030 Uiso 1 1 calc R . . C13 C 0.43649(8) 0.9418(3) 0.76865(10) 0.0266(4) Uani 1 1 d . . . H13 H 0.4781 0.9295 0.7892 0.032 Uiso 1 1 calc R . . C14 C 0.40475(8) 0.7838(3) 0.77111(10) 0.0250(4) Uani 1 1 d . . . H14 H 0.4246 0.6633 0.7927 0.030 Uiso 1 1 calc R . . C15 C 0.34392(7) 0.8020(3) 0.74197(10) 0.0205(3) Uani 1 1 d . . . H15 H 0.3223 0.6937 0.7436 0.025 Uiso 1 1 calc R . . Cl Cl 0.227474(17) 0.48976(5) 0.60302(2) 0.01928(9) 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 0.0112(6) 0.0134(6) 0.0152(6) -0.0005(5) 0.0059(5) 0.0008(5) C2 0.0150(7) 0.0192(7) 0.0185(7) -0.0026(6) 0.0104(6) -0.0017(6) C3 0.0182(7) 0.0171(7) 0.0228(8) 0.0012(6) 0.0118(6) -0.0015(6) C4 0.0196(8) 0.0157(7) 0.0237(8) -0.0035(6) 0.0088(7) -0.0044(6) C5 0.0181(7) 0.0199(7) 0.0153(7) -0.0040(6) 0.0059(6) 0.0001(6) C6 0.0128(7) 0.0189(7) 0.0150(7) 0.0018(6) 0.0053(6) 0.0017(6) Br 0.01452(9) 0.02109(10) 0.02428(10) 0.00585(6) 0.00473(7) 0.00332(6) C7 0.0167(7) 0.0357(10) 0.0155(7) 0.0062(7) 0.0072(6) -0.0011(7) C8 0.0152(7) 0.0182(7) 0.0132(6) 0.0006(5) 0.0090(6) 0.0002(5) N 0.0116(6) 0.0114(6) 0.0132(6) 0.0011(4) 0.0061(5) 0.0011(4) C9 0.0134(7) 0.0169(7) 0.0126(6) -0.0002(5) 0.0060(6) 0.0005(5) C10 0.0138(7) 0.0195(7) 0.0119(6) 0.0005(5) 0.0061(6) 0.0008(6) C11 0.0170(8) 0.0226(8) 0.0165(7) 0.0027(6) 0.0071(6) -0.0009(6) C12 0.0166(8) 0.0387(10) 0.0178(8) 0.0037(7) 0.0075(7) -0.0042(7) C13 0.0143(7) 0.0482(11) 0.0162(7) 0.0041(7) 0.0075(6) 0.0051(7) C14 0.0210(8) 0.0316(9) 0.0191(8) 0.0053(7) 0.0086(7) 0.0102(7) C15 0.0196(8) 0.0211(8) 0.0188(7) 0.0035(6) 0.0090(6) 0.0028(6) Cl 0.02086(18) 0.01202(17) 0.02616(19) 0.00198(13) 0.01340(16) 0.00335(13) _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 N 1.5216(18) . ? C1 C2 1.524(2) . ? C1 C6 1.537(2) . ? C1 H1 1.0000 . ? C2 C3 1.531(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.526(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.526(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.526(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.535(2) . ? C6 Br 1.9764(16) . ? C7 C8 1.536(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N 1.5169(18) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? N C9 1.5112(19) . ? N H1N 0.89(2) . ? C9 C10 1.511(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.397(2) . ? C10 C15 1.398(2) . ? C11 C12 1.395(2) . ? C11 H11 0.9500 . ? C12 C13 1.385(3) . ? C12 H12 0.9500 . ? C13 C14 1.390(3) . ? C13 H13 0.9500 . ? C14 C15 1.394(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? 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 N C1 C2 114.80(12) . . ? N C1 C6 101.47(11) . . ? C2 C1 C6 115.11(12) . . ? N C1 H1 108.4 . . ? C2 C1 H1 108.4 . . ? C6 C1 H1 108.4 . . ? C1 C2 C3 114.17(13) . . ? C1 C2 H2A 108.7 . . ? C3 C2 H2A 108.7 . . ? C1 C2 H2B 108.7 . . ? C3 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? C4 C3 C2 110.98(13) . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3B 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 110.65(13) . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C4 C5 C6 112.94(13) . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? C4 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C5 C6 C7 113.64(14) . . ? C5 C6 C1 112.68(13) . . ? C7 C6 C1 103.84(12) . . ? C5 C6 Br 108.29(10) . . ? C7 C6 Br 110.10(11) . . ? C1 C6 Br 108.14(10) . . ? C6 C7 C8 105.24(13) . . ? C6 C7 H7A 110.7 . . ? C8 C7 H7A 110.7 . . ? C6 C7 H7B 110.7 . . ? C8 C7 H7B 110.7 . . ? H7A C7 H7B 108.8 . . ? N C8 C7 106.34(12) . . ? N C8 H8A 110.5 . . ? C7 C8 H8A 110.5 . . ? N C8 H8B 110.5 . . ? C7 C8 H8B 110.5 . . ? H8A C8 H8B 108.7 . . ? C9 N C8 113.79(12) . . ? C9 N C1 112.18(11) . . ? C8 N C1 105.26(11) . . ? C9 N H1N 108.2(13) . . ? C8 N H1N 106.4(13) . . ? C1 N H1N 110.8(14) . . ? C10 C9 N 113.60(12) . . ? C10 C9 H9A 108.8 . . ? N C9 H9A 108.8 . . ? C10 C9 H9B 108.8 . . ? N C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C11 C10 C15 119.29(15) . . ? C11 C10 C9 119.44(14) . . ? C15 C10 C9 121.24(14) . . ? C12 C11 C10 120.34(15) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C13 C12 C11 119.97(16) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 120.16(16) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C15 120.10(17) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C14 C15 C10 120.13(16) . . ? C14 C15 H15 119.9 . . ? C10 C15 H15 119.9 . . ? 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 N C1 C2 C3 -73.53(17) . . . . ? C6 C1 C2 C3 43.77(18) . . . . ? C1 C2 C3 C4 -50.87(18) . . . . ? C2 C3 C4 C5 57.32(18) . . . . ? C3 C4 C5 C6 -57.68(18) . . . . ? C4 C5 C6 C7 167.28(13) . . . . ? C4 C5 C6 C1 49.51(18) . . . . ? C4 C5 C6 Br -70.06(15) . . . . ? N C1 C6 C5 82.21(14) . . . . ? C2 C1 C6 C5 -42.39(18) . . . . ? N C1 C6 C7 -41.19(15) . . . . ? C2 C1 C6 C7 -165.80(13) . . . . ? N C1 C6 Br -158.14(9) . . . . ? C2 C1 C6 Br 77.26(14) . . . . ? C5 C6 C7 C8 -94.97(16) . . . . ? C1 C6 C7 C8 27.81(17) . . . . ? Br C6 C7 C8 143.37(11) . . . . ? C6 C7 C8 N -3.53(17) . . . . ? C7 C8 N C9 -145.66(13) . . . . ? C7 C8 N C1 -22.44(16) . . . . ? C2 C1 N C9 -71.66(16) . . . . ? C6 C1 N C9 163.53(12) . . . . ? C2 C1 N C8 164.09(12) . . . . ? C6 C1 N C8 39.27(14) . . . . ? C8 N C9 C10 -47.07(17) . . . . ? C1 N C9 C10 -166.44(12) . . . . ? N C9 C10 C11 100.36(16) . . . . ? N C9 C10 C15 -81.62(17) . . . . ? C15 C10 C11 C12 -0.3(2) . . . . ? C9 C10 C11 C12 177.76(15) . . . . ? C10 C11 C12 C13 -0.7(3) . . . . ? C11 C12 C13 C14 1.2(3) . . . . ? C12 C13 C14 C15 -0.8(3) . . . . ? C13 C14 C15 C10 -0.1(3) . . . . ? C11 C10 C15 C14 0.7(2) . . . . ? C9 C10 C15 C14 -177.33(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N H1N Cl 0.89(2) 2.20(2) 3.0785(14) 169.9(19) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.272 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.083 # Attachment 'eva36.cif' data_eva36 _database_code_depnum_ccdc_archive 'CCDC 707948' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H21 N O2 S' _chemical_formula_sum 'C15 H21 N O2 S' _chemical_formula_weight 279.39 _chemical_absolute_configuration unk 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.237(2) _cell_length_b 12.419(4) _cell_length_c 17.923(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1388.2(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1205 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 21.95 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.337 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3275 _exptl_absorpt_correction_T_max 0.9954 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.122 before and 0.075 after correction. The Ratio of minimum to maximum transmission is 0.828605. The \l/2 correction factor is 0.0015 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5752 _diffrn_reflns_av_R_equivalents 0.0877 _diffrn_reflns_av_sigmaI/netI 0.0798 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 22.06 _reflns_number_total 1710 _reflns_number_gt 1516 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0659P)^2^+0.6572P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'fixed to racemic mixture' _refine_ls_abs_structure_Flack 0.5 _refine_ls_number_reflns 1710 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1371 _refine_ls_wR_factor_gt 0.1326 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.001 _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 S S 0.2224(2) 0.46353(10) 0.32741(6) 0.0254(4) Uani 1 1 d . . . O1 O -0.0034(5) 0.4695(3) 0.33209(18) 0.0305(9) Uani 1 1 d . . . O2 O 0.3213(6) 0.3945(3) 0.27314(17) 0.0349(10) Uani 1 1 d . . . C1 C 0.3172(8) 0.4233(4) 0.4166(3) 0.0227(12) Uani 1 1 d . . . C2 C 0.1926(8) 0.4429(4) 0.4778(3) 0.0261(12) Uani 1 1 d . . . H2 H 0.0546 0.4745 0.4724 0.031 Uiso 1 1 calc R . . C3 C 0.2703(9) 0.4161(4) 0.5479(3) 0.0296(13) Uani 1 1 d . . . H3 H 0.1851 0.4303 0.5907 0.036 Uiso 1 1 calc R . . C4 C 0.4696(9) 0.3692(4) 0.5564(3) 0.0273(13) Uani 1 1 d . . . C7 C 0.5468(10) 0.3352(4) 0.6313(3) 0.0399(15) Uani 1 1 d . . . H7A H 0.5106 0.2593 0.6395 0.060 Uiso 1 1 calc R . . H7B H 0.4781 0.3794 0.6697 0.060 Uiso 1 1 calc R . . H7C H 0.7027 0.3444 0.6340 0.060 Uiso 1 1 calc R . . C5 C 0.5934(9) 0.3516(4) 0.4928(3) 0.0286(13) Uani 1 1 d . . . H5 H 0.7317 0.3203 0.4977 0.034 Uiso 1 1 calc R . . C6 C 0.5187(8) 0.3788(4) 0.4233(3) 0.0280(13) Uani 1 1 d . . . H6 H 0.6048 0.3671 0.3804 0.034 Uiso 1 1 calc R . . N N 0.3093(7) 0.5833(3) 0.3114(2) 0.0266(11) Uani 1 1 d . . . C8 C 0.5400(9) 0.6007(5) 0.2958(3) 0.0395(15) Uani 1 1 d . . . H8A H 0.5612 0.6234 0.2434 0.047 Uiso 1 1 calc R . . H8B H 0.6221 0.5336 0.3045 0.047 Uiso 1 1 calc R . . C9 C 0.6139(9) 0.6895(4) 0.3495(3) 0.0315(13) Uani 1 1 d . . . H9A H 0.7491 0.6687 0.3746 0.038 Uiso 1 1 calc R . . H9B H 0.6374 0.7579 0.3223 0.038 Uiso 1 1 calc R . . C10 C 0.4324(8) 0.7016(4) 0.4063(3) 0.0257(12) Uani 1 1 d . . . H10 H 0.4498 0.6455 0.4459 0.031 Uiso 1 1 calc R . . C11 C 0.4176(9) 0.8119(4) 0.4433(3) 0.0246(12) Uani 1 1 d . . . H11A H 0.3214 0.8064 0.4871 0.030 Uiso 1 1 calc R . . H11B H 0.5616 0.8322 0.4617 0.030 Uiso 1 1 calc R . . C12 C 0.3356(8) 0.9008(4) 0.3926(3) 0.0313(14) Uani 1 1 d . . . H12A H 0.4419 0.9151 0.3528 0.038 Uiso 1 1 calc R . . H12B H 0.3160 0.9677 0.4218 0.038 Uiso 1 1 calc R . . C13 C 0.1228(9) 0.8675(4) 0.3578(3) 0.0348(14) Uani 1 1 d . . . H13A H 0.0160 0.8532 0.3974 0.042 Uiso 1 1 calc R . . H13B H 0.0676 0.9263 0.3258 0.042 Uiso 1 1 calc R . . C14 C 0.1569(8) 0.7664(4) 0.3112(3) 0.0300(14) Uani 1 1 d . . . H14A H 0.0203 0.7460 0.2869 0.036 Uiso 1 1 calc R . . H14B H 0.2633 0.7813 0.2716 0.036 Uiso 1 1 calc R . . C15 C 0.2351(8) 0.6739(4) 0.3590(3) 0.0238(12) Uani 1 1 d . . . H15 H 0.1164 0.6487 0.3922 0.029 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 S 0.0295(8) 0.0324(8) 0.0145(7) -0.0069(6) -0.0037(6) -0.0020(6) O1 0.031(2) 0.034(2) 0.026(2) -0.0047(18) -0.0058(16) -0.0049(16) O2 0.044(3) 0.043(2) 0.0179(19) -0.0144(17) -0.0024(16) 0.0036(18) C1 0.029(3) 0.022(3) 0.017(3) -0.003(2) 0.000(2) 0.001(2) C2 0.032(3) 0.023(3) 0.023(3) 0.000(2) -0.004(2) 0.003(2) C3 0.045(4) 0.030(3) 0.013(3) -0.004(2) 0.005(2) 0.004(3) C4 0.036(3) 0.025(3) 0.021(3) 0.000(2) 0.000(2) -0.007(2) C7 0.056(4) 0.036(4) 0.027(3) 0.008(3) -0.003(3) 0.000(3) C5 0.034(3) 0.024(3) 0.028(3) -0.003(2) -0.005(3) 0.000(2) C6 0.025(3) 0.036(3) 0.023(3) -0.005(2) 0.006(2) 0.004(3) N 0.035(3) 0.033(3) 0.011(2) -0.0085(18) 0.0015(18) -0.0022(19) C8 0.047(4) 0.046(4) 0.026(3) -0.001(3) 0.012(3) 0.000(3) C9 0.030(3) 0.034(3) 0.030(3) 0.004(2) 0.004(3) -0.004(2) C10 0.026(3) 0.034(3) 0.017(3) 0.004(2) -0.005(2) -0.002(2) C11 0.030(3) 0.031(3) 0.013(2) 0.002(2) -0.002(2) -0.006(3) C12 0.042(4) 0.030(3) 0.022(3) -0.001(2) -0.006(2) -0.003(2) C13 0.044(3) 0.035(3) 0.025(3) -0.001(2) -0.012(3) 0.003(3) C14 0.034(3) 0.044(4) 0.013(3) 0.004(2) -0.010(2) -0.006(2) C15 0.026(3) 0.031(3) 0.014(2) -0.002(2) 0.000(2) -0.005(2) _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 S O1 1.412(3) . ? S O2 1.436(3) . ? S N 1.609(4) . ? S C1 1.776(5) . ? C1 C2 1.366(7) . ? C1 C6 1.378(7) . ? C2 C3 1.387(7) . ? C2 H2 0.9500 . ? C3 C4 1.381(8) . ? C3 H3 0.9500 . ? C4 C5 1.395(7) . ? C4 C7 1.487(7) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C5 C6 1.372(7) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? N C8 1.481(7) . ? N C15 1.486(6) . ? C8 C9 1.535(7) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.531(7) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.524(7) . ? C10 C15 1.533(7) . ? C10 H10 1.0000 . ? C11 C12 1.518(7) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.524(7) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.522(8) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.514(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15 1.0000 . ? 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 O1 S O2 120.0(2) . . ? O1 S N 107.3(2) . . ? O2 S N 106.6(2) . . ? O1 S C1 107.1(2) . . ? O2 S C1 107.4(2) . . ? N S C1 108.0(2) . . ? C2 C1 C6 121.3(5) . . ? C2 C1 S 118.9(4) . . ? C6 C1 S 119.7(4) . . ? C1 C2 C3 119.1(5) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 121.1(5) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 118.3(5) . . ? C3 C4 C7 120.8(5) . . ? C5 C4 C7 120.9(5) . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C5 C4 121.0(5) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 119.2(5) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? C8 N C15 107.5(4) . . ? C8 N S 119.7(4) . . ? C15 N S 119.5(3) . . ? N C8 C9 106.2(4) . . ? N C8 H8A 110.5 . . ? C9 C8 H8A 110.5 . . ? N C8 H8B 110.5 . . ? C9 C8 H8B 110.5 . . ? H8A C8 H8B 108.7 . . ? C10 C9 C8 105.4(4) . . ? C10 C9 H9A 110.7 . . ? C8 C9 H9A 110.7 . . ? C10 C9 H9B 110.7 . . ? C8 C9 H9B 110.7 . . ? H9A C9 H9B 108.8 . . ? C11 C10 C9 114.9(4) . . ? C11 C10 C15 113.2(4) . . ? C9 C10 C15 101.7(4) . . ? C11 C10 H10 108.9 . . ? C9 C10 H10 108.9 . . ? C15 C10 H10 108.9 . . ? C12 C11 C10 114.5(4) . . ? C12 C11 H11A 108.6 . . ? C10 C11 H11A 108.6 . . ? C12 C11 H11B 108.6 . . ? C10 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? C11 C12 C13 110.0(4) . . ? C11 C12 H12A 109.7 . . ? C13 C12 H12A 109.7 . . ? C11 C12 H12B 109.7 . . ? C13 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? C14 C13 C12 109.1(4) . . ? C14 C13 H13A 109.9 . . ? C12 C13 H13A 109.9 . . ? C14 C13 H13B 109.9 . . ? C12 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? C15 C14 C13 111.1(4) . . ? C15 C14 H14A 109.4 . . ? C13 C14 H14A 109.4 . . ? C15 C14 H14B 109.4 . . ? C13 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? N C15 C14 110.4(4) . . ? N C15 C10 103.8(4) . . ? C14 C15 C10 113.7(4) . . ? N C15 H15 109.6 . . ? C14 C15 H15 109.6 . . ? C10 C15 H15 109.6 . . ? 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 O1 S C1 C2 -23.8(4) . . . . ? O2 S C1 C2 -153.9(4) . . . . ? N S C1 C2 91.5(4) . . . . ? O1 S C1 C6 159.8(4) . . . . ? O2 S C1 C6 29.7(4) . . . . ? N S C1 C6 -84.9(4) . . . . ? C6 C1 C2 C3 -0.7(7) . . . . ? S C1 C2 C3 -177.1(4) . . . . ? C1 C2 C3 C4 -0.7(8) . . . . ? C2 C3 C4 C5 1.4(8) . . . . ? C2 C3 C4 C7 -176.6(5) . . . . ? C3 C4 C5 C6 -0.8(8) . . . . ? C7 C4 C5 C6 177.2(5) . . . . ? C4 C5 C6 C1 -0.6(8) . . . . ? C2 C1 C6 C5 1.4(7) . . . . ? S C1 C6 C5 177.7(4) . . . . ? O1 S N C8 -173.7(3) . . . . ? O2 S N C8 -43.9(4) . . . . ? C1 S N C8 71.2(4) . . . . ? O1 S N C15 50.3(4) . . . . ? O2 S N C15 -179.9(3) . . . . ? C1 S N C15 -64.8(4) . . . . ? C15 N C8 C9 12.5(5) . . . . ? S N C8 C9 -128.2(4) . . . . ? N C8 C9 C10 12.7(5) . . . . ? C8 C9 C10 C11 -154.4(4) . . . . ? C8 C9 C10 C15 -31.7(5) . . . . ? C9 C10 C11 C12 72.2(6) . . . . ? C15 C10 C11 C12 -44.1(6) . . . . ? C10 C11 C12 C13 53.4(6) . . . . ? C11 C12 C13 C14 -61.0(5) . . . . ? C12 C13 C14 C15 61.2(6) . . . . ? C8 N C15 C14 89.4(5) . . . . ? S N C15 C14 -129.8(4) . . . . ? C8 N C15 C10 -32.7(5) . . . . ? S N C15 C10 108.0(4) . . . . ? C13 C14 C15 N -168.6(4) . . . . ? C13 C14 C15 C10 -52.4(6) . . . . ? C11 C10 C15 N 163.2(4) . . . . ? C9 C10 C15 N 39.4(4) . . . . ? C11 C10 C15 C14 43.2(5) . . . . ? C9 C10 C15 C14 -80.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 22.06 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.379 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.064 # Attachment 'eva40.cif' data_eva40 _database_code_depnum_ccdc_archive 'CCDC 707949' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H14 O2' _chemical_formula_sum 'C9 H14 O2' _chemical_formula_weight 154.20 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' _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 7.3608(7) _cell_length_b 12.1760(11) _cell_length_c 15.1409(14) _cell_angle_alpha 103.092(2) _cell_angle_beta 93.820(2) _cell_angle_gamma 100.303(2) _cell_volume 1292.3(2) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4395 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8929 _exptl_absorpt_correction_T_max 0.9975 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.130 before and 0.029 after correction. The Ratio of minimum to maximum transmission is 0.895089. The \l/2 correction factor is 0.0015 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19207 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 24.17 _reflns_number_total 4122 _reflns_number_gt 3522 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0354P)^2^+0.3387P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4122 _refine_ls_number_parameters 329 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0850 _refine_ls_wR_factor_gt 0.0810 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.001 _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 1.41074(12) -0.00126(8) 0.89724(6) 0.0223(2) Uani 1 1 d . . . O2 O 1.29024(14) 0.05471(8) 1.02761(6) 0.0246(2) Uani 1 1 d . . . H1O2 H 1.400(3) 0.0375(16) 1.0515(13) 0.061(6) Uiso 1 1 d . . . C1 C 1.28615(19) 0.03351(11) 0.93757(9) 0.0196(3) Uani 1 1 d . . . C2 C 1.11518(18) 0.05550(12) 0.89161(9) 0.0208(3) Uani 1 1 d . . . H2A H 1.0954 0.1326 0.9224 0.025 Uiso 1 1 calc R . . H2B H 1.0069 -0.0019 0.8985 0.025 Uiso 1 1 calc R . . C3 C 1.12487(19) 0.04962(13) 0.79085(9) 0.0241(3) Uani 1 1 d . . . H3A H 1.2250 0.1129 0.7852 0.029 Uiso 1 1 calc R . . H3B H 1.1612 -0.0237 0.7624 0.029 Uiso 1 1 calc R . . C4 C 0.95015(18) 0.05732(11) 0.73709(9) 0.0203(3) Uani 1 1 d . A . C5 C 0.79474(18) 0.07497(11) 0.77179(9) 0.0215(3) Uani 1 1 d . A . H5 H 0.7941 0.0866 0.8360 0.026 Uiso 1 1 calc R . . C6 C 0.61939(19) 0.07782(13) 0.71673(9) 0.0260(3) Uani 1 1 d D . . H6A H 0.6022 0.1584 0.7270 0.031 Uiso 0.887(6) 1 calc PR A 1 H6B H 0.5125 0.0331 0.7381 0.031 Uiso 0.887(6) 1 calc PR A 1 H6C H 0.5648 0.1425 0.7485 0.031 Uiso 0.113(6) 1 d PR A 2 H6D H 0.5284 0.0055 0.7113 0.031 Uiso 0.113(6) 1 d PR A 2 C7A C 0.6213(3) 0.0290(2) 0.61567(12) 0.0256(5) Uani 0.887(6) 1 d PD A 1 H7A1 H 0.5193 0.0499 0.5810 0.031 Uiso 0.887(6) 1 calc PR A 1 H7A2 H 0.6008 -0.0560 0.6026 0.031 Uiso 0.887(6) 1 calc PR A 1 C8A C 0.8062(3) 0.0758(2) 0.58558(15) 0.0266(6) Uani 0.887(6) 1 d PD A 1 H8A1 H 0.8262 0.1607 0.5983 0.032 Uiso 0.887(6) 1 calc PR A 1 H8A2 H 0.8043 0.0453 0.5190 0.032 Uiso 0.887(6) 1 calc PR A 1 C7B C 0.657(2) 0.0926(18) 0.6186(9) 0.028(4) Uani 0.113(6) 1 d PD A 2 H7B1 H 0.5377 0.0763 0.5795 0.034 Uiso 0.113(6) 1 calc PR A 2 H7B2 H 0.7188 0.1731 0.6227 0.034 Uiso 0.113(6) 1 calc PR A 2 C8B C 0.778(2) 0.0132(19) 0.5761(12) 0.043(6) Uani 0.113(6) 1 d PD A 2 H8B1 H 0.7987 0.0231 0.5142 0.052 Uiso 0.113(6) 1 calc PR A 2 H8B2 H 0.7165 -0.0676 0.5707 0.052 Uiso 0.113(6) 1 calc PR A 2 C9 C 0.9646(2) 0.04104(14) 0.63609(9) 0.0276(3) Uani 1 1 d D . . H9A H 0.9656 -0.0408 0.6090 0.033 Uiso 0.887(6) 1 calc PR A 1 H9B H 1.0840 0.0873 0.6273 0.033 Uiso 0.887(6) 1 calc PR A 1 H9C H 1.0321 -0.0221 0.6162 0.033 Uiso 0.113(6) 1 d PR A 2 H9D H 1.0403 0.1121 0.6261 0.033 Uiso 0.113(6) 1 d PR A 2 O3 O 0.98520(13) 0.75467(8) 0.84782(6) 0.0268(2) Uani 1 1 d . . . O4 O 0.80338(14) 0.66424(8) 0.93265(6) 0.0255(2) Uani 1 1 d . . . H1O4 H 0.920(3) 0.6683(16) 0.9661(13) 0.060(6) Uiso 1 1 d . . . C10 C 0.83142(19) 0.70753(11) 0.86092(9) 0.0221(3) Uani 1 1 d . . . C11 C 0.65756(19) 0.69086(12) 0.79912(9) 0.0243(3) Uani 1 1 d . . . H11A H 0.5685 0.7305 0.8336 0.029 Uiso 1 1 calc R . . H11B H 0.6017 0.6077 0.7808 0.029 Uiso 1 1 calc R . . C12 C 0.68281(19) 0.73472(13) 0.71333(10) 0.0266(3) Uani 1 1 d . . . H12A H 0.7344 0.8185 0.7311 0.032 Uiso 1 1 calc R . . H12B H 0.7737 0.6966 0.6791 0.032 Uiso 1 1 calc R . . C13 C 0.50415(19) 0.71284(12) 0.65216(9) 0.0239(3) Uani 1 1 d . . . C14 C 0.4866(2) 0.65827(14) 0.56472(10) 0.0341(4) Uani 1 1 d . . . H14 H 0.5918 0.6320 0.5412 0.041 Uiso 1 1 calc R . . C15 C 0.3118(2) 0.63487(16) 0.50004(11) 0.0441(5) Uani 1 1 d . . . H15A H 0.2886 0.5541 0.4637 0.053 Uiso 1 1 calc R . . H15B H 0.3291 0.6856 0.4573 0.053 Uiso 1 1 calc R . . C16 C 0.1445(2) 0.65503(14) 0.54995(11) 0.0373(4) Uani 1 1 d . . . H16A H 0.1023 0.5898 0.5775 0.045 Uiso 1 1 calc R . . H16B H 0.0414 0.6595 0.5063 0.045 Uiso 1 1 calc R . . C17 C 0.1941(2) 0.76611(13) 0.62414(10) 0.0281(3) Uani 1 1 d . . . H17A H 0.0823 0.7808 0.6540 0.034 Uiso 1 1 calc R . . H17B H 0.2382 0.8311 0.5966 0.034 Uiso 1 1 calc R . . C18 C 0.34474(19) 0.75849(13) 0.69477(9) 0.0261(3) Uani 1 1 d . . . H18A H 0.3925 0.8359 0.7353 0.031 Uiso 1 1 calc R . . H18B H 0.2901 0.7076 0.7328 0.031 Uiso 1 1 calc R . . O5 O 0.11047(13) 0.66613(9) 0.02970(7) 0.0284(2) Uani 1 1 d . . . O6 O 0.29850(14) 0.76291(8) -0.04870(7) 0.0279(3) Uani 1 1 d . . . H1O6 H 0.184(3) 0.7621(18) -0.0816(14) 0.075(7) Uiso 1 1 d . . . C19 C 0.26641(19) 0.70861(11) 0.01683(9) 0.0211(3) Uani 1 1 d . . . C20 C 0.43746(19) 0.70517(12) 0.07365(9) 0.0223(3) Uani 1 1 d . . . H20A H 0.4910 0.7837 0.1109 0.027 Uiso 1 1 calc R . . H20B H 0.5301 0.6806 0.0329 0.027 Uiso 1 1 calc R . . C21 C 0.40240(19) 0.62393(12) 0.13684(10) 0.0246(3) Uani 1 1 d . . . H21A H 0.3146 0.6509 0.1796 0.029 Uiso 1 1 calc R . . H21B H 0.3428 0.5462 0.0998 0.029 Uiso 1 1 calc R . . C22 C 0.57627(19) 0.61567(11) 0.19100(9) 0.0223(3) Uani 1 1 d . . . C23 C 0.5951(2) 0.63832(12) 0.28135(10) 0.0279(3) Uani 1 1 d . . . H23 H 0.4952 0.6626 0.3119 0.034 Uiso 1 1 calc R . . C24 C 0.7627(2) 0.62847(14) 0.33899(10) 0.0337(4) Uani 1 1 d . . . H24A H 0.7309 0.5611 0.3654 0.040 Uiso 1 1 calc R . . H24B H 0.7982 0.6980 0.3900 0.040 Uiso 1 1 calc R . . C25 C 0.9274(2) 0.61523(13) 0.28433(10) 0.0316(4) Uani 1 1 d . . . H25A H 0.9860 0.6910 0.2752 0.038 Uiso 1 1 calc R . . H25B H 1.0211 0.5873 0.3188 0.038 Uiso 1 1 calc R . . C26 C 0.8648(2) 0.53096(13) 0.19235(10) 0.0284(3) Uani 1 1 d . . . H26A H 0.8053 0.4553 0.2013 0.034 Uiso 1 1 calc R . . H26B H 0.9738 0.5206 0.1587 0.034 Uiso 1 1 calc R . . C27 C 0.7275(2) 0.57621(13) 0.13727(9) 0.0275(3) Uani 1 1 d . . . H27A H 0.7955 0.6414 0.1160 0.033 Uiso 1 1 calc R . . H27B H 0.6703 0.5147 0.0827 0.033 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 O1 0.0196(5) 0.0298(5) 0.0193(5) 0.0076(4) 0.0023(4) 0.0075(4) O2 0.0210(5) 0.0378(6) 0.0175(5) 0.0084(4) 0.0015(4) 0.0102(5) C1 0.0183(7) 0.0178(7) 0.0214(7) 0.0062(6) 0.0017(6) -0.0012(6) C2 0.0179(7) 0.0228(7) 0.0216(7) 0.0054(6) 0.0002(6) 0.0041(6) C3 0.0195(7) 0.0324(8) 0.0217(7) 0.0082(6) 0.0022(6) 0.0068(6) C4 0.0205(7) 0.0209(7) 0.0200(7) 0.0060(6) 0.0005(6) 0.0047(6) C5 0.0222(8) 0.0247(7) 0.0180(7) 0.0051(6) 0.0005(6) 0.0060(6) C6 0.0199(8) 0.0364(8) 0.0234(8) 0.0078(6) 0.0019(6) 0.0096(6) C7A 0.0217(11) 0.0314(13) 0.0226(9) 0.0060(9) -0.0029(7) 0.0056(10) C8A 0.0274(11) 0.0368(14) 0.0181(9) 0.0094(11) 0.0004(8) 0.0102(10) C7B 0.025(9) 0.031(10) 0.027(8) 0.014(8) -0.011(6) -0.004(8) C8B 0.058(13) 0.053(14) 0.034(10) 0.028(11) 0.014(9) 0.026(12) C9 0.0237(8) 0.0404(9) 0.0220(8) 0.0105(7) 0.0042(6) 0.0105(7) O3 0.0197(6) 0.0328(6) 0.0295(6) 0.0134(5) 0.0005(4) 0.0027(4) O4 0.0210(5) 0.0323(6) 0.0245(5) 0.0116(4) -0.0001(4) 0.0034(4) C10 0.0230(8) 0.0200(7) 0.0237(8) 0.0046(6) 0.0028(6) 0.0059(6) C11 0.0212(8) 0.0262(8) 0.0250(8) 0.0074(6) 0.0001(6) 0.0027(6) C12 0.0220(8) 0.0323(8) 0.0279(8) 0.0117(6) 0.0039(6) 0.0055(6) C13 0.0251(8) 0.0245(8) 0.0253(8) 0.0116(6) 0.0020(6) 0.0062(6) C14 0.0388(9) 0.0437(10) 0.0252(8) 0.0085(7) 0.0040(7) 0.0223(8) C15 0.0564(12) 0.0487(11) 0.0261(9) -0.0013(8) -0.0096(8) 0.0262(9) C16 0.0374(10) 0.0363(9) 0.0347(9) 0.0075(7) -0.0139(7) 0.0066(7) C17 0.0226(8) 0.0324(8) 0.0317(8) 0.0125(7) 0.0013(6) 0.0063(6) C18 0.0240(8) 0.0295(8) 0.0239(8) 0.0060(6) 0.0008(6) 0.0045(6) O5 0.0193(6) 0.0389(6) 0.0283(6) 0.0139(5) 0.0015(4) 0.0026(5) O6 0.0217(6) 0.0341(6) 0.0302(6) 0.0173(5) -0.0013(5) 0.0008(5) C19 0.0225(8) 0.0186(7) 0.0214(7) 0.0028(6) 0.0029(6) 0.0043(6) C20 0.0192(7) 0.0237(7) 0.0230(7) 0.0058(6) -0.0003(6) 0.0022(6) C21 0.0210(8) 0.0251(8) 0.0264(8) 0.0080(6) -0.0005(6) 0.0005(6) C22 0.0223(8) 0.0190(7) 0.0249(8) 0.0072(6) 0.0007(6) 0.0011(6) C23 0.0282(8) 0.0321(8) 0.0273(8) 0.0112(7) 0.0049(6) 0.0105(7) C24 0.0402(10) 0.0384(9) 0.0240(8) 0.0099(7) -0.0019(7) 0.0109(7) C25 0.0283(8) 0.0348(9) 0.0314(9) 0.0103(7) -0.0056(7) 0.0058(7) C26 0.0253(8) 0.0293(8) 0.0317(8) 0.0082(7) 0.0015(6) 0.0075(6) C27 0.0285(8) 0.0315(8) 0.0219(8) 0.0046(6) -0.0003(6) 0.0085(7) _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 C1 1.2205(16) . ? O2 C1 1.3261(16) . ? O2 H1O2 0.94(2) . ? C1 C2 1.4926(19) . ? C2 C3 1.5180(19) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5045(19) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.3220(19) . ? C4 C9 1.5102(19) . ? C5 C6 1.4993(19) . ? C5 H5 0.9500 . ? C6 C7A 1.513(2) . ? C6 C7B 1.574(13) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C6 H6C 0.9900 . ? C6 H6D 0.9900 . ? C7A C8A 1.519(3) . ? C7A H7A1 0.9900 . ? C7A H7A2 0.9900 . ? C8A C9 1.526(2) . ? C8A H8A1 0.9900 . ? C8A H8A2 0.9900 . ? C7B C8B 1.496(17) . ? C7B H7B1 0.9900 . ? C7B H7B2 0.9900 . ? C8B C9 1.534(15) . ? C8B H8B1 0.9900 . ? C8B H8B2 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C9 H9C 0.9900 . ? C9 H9D 0.9900 . ? O3 C10 1.2244(16) . ? O4 C10 1.3231(16) . ? O4 H1O4 0.96(2) . ? C10 C11 1.4886(19) . ? C11 C12 1.5225(19) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.5029(19) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.326(2) . ? C13 C18 1.508(2) . ? C14 C15 1.507(2) . ? C14 H14 0.9500 . ? C15 C16 1.515(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.518(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.518(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? O5 C19 1.2191(16) . ? O6 C19 1.3229(16) . ? O6 H1O6 0.95(2) . ? C19 C20 1.4893(19) . ? C20 C21 1.5266(18) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.5047(19) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.3253(19) . ? C22 C27 1.506(2) . ? C23 C24 1.502(2) . ? C23 H23 0.9500 . ? C24 C25 1.524(2) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.517(2) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.522(2) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? 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 O2 H1O2 108.5(11) . . ? O1 C1 O2 122.51(12) . . ? O1 C1 C2 124.05(12) . . ? O2 C1 C2 113.43(12) . . ? C1 C2 C3 113.13(11) . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2B 109.0 . . ? C3 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C4 C3 C2 116.48(11) . . ? C4 C3 H3A 108.2 . . ? C2 C3 H3A 108.2 . . ? C4 C3 H3B 108.2 . . ? C2 C3 H3B 108.2 . . ? H3A C3 H3B 107.3 . . ? C5 C4 C3 125.10(12) . . ? C5 C4 C9 121.21(12) . . ? C3 C4 C9 113.69(11) . . ? C4 C5 C6 124.43(12) . . ? C4 C5 H5 117.8 . . ? C6 C5 H5 117.8 . . ? C5 C6 C7A 112.52(13) . . ? C5 C6 C7B 111.3(6) . . ? C7A C6 C7B 28.5(7) . . ? C5 C6 H6A 109.1 . . ? C7A C6 H6A 109.1 . . ? C7B C6 H6A 83.6 . . ? C5 C6 H6B 109.1 . . ? C7A C6 H6B 109.1 . . ? C7B C6 H6B 131.2 . . ? H6A C6 H6B 107.8 . . ? C5 C6 H6C 109.4 . . ? C7A C6 H6C 129.8 . . ? C7B C6 H6C 109.4 . . ? H6A C6 H6C 28.7 . . ? H6B C6 H6C 81.1 . . ? C5 C6 H6D 109.4 . . ? C7A C6 H6D 82.9 . . ? C7B C6 H6D 109.3 . . ? H6A C6 H6D 130.7 . . ? H6B C6 H6D 29.3 . . ? H6C C6 H6D 108.0 . . ? C6 C7A C8A 110.28(19) . . ? C6 C7A H7A1 109.6 . . ? C8A C7A H7A1 109.6 . . ? C6 C7A H7A2 109.6 . . ? C8A C7A H7A2 109.6 . . ? H7A1 C7A H7A2 108.1 . . ? C7A C8A C9 110.36(18) . . ? C7A C8A H8A1 109.6 . . ? C9 C8A H8A1 109.6 . . ? C7A C8A H8A2 109.6 . . ? C9 C8A H8A2 109.6 . . ? H8A1 C8A H8A2 108.1 . . ? C8B C7B C6 111.2(13) . . ? C8B C7B H7B1 109.4 . . ? C6 C7B H7B1 109.4 . . ? C8B C7B H7B2 109.4 . . ? C6 C7B H7B2 109.4 . . ? H7B1 C7B H7B2 108.0 . . ? C7B C8B C9 108.9(14) . . ? C7B C8B H8B1 109.9 . . ? C9 C8B H8B1 109.9 . . ? C7B C8B H8B2 109.9 . . ? C9 C8B H8B2 109.9 . . ? H8B1 C8B H8B2 108.3 . . ? C4 C9 C8A 113.30(13) . . ? C4 C9 C8B 114.9(7) . . ? C8A C9 C8B 27.6(8) . . ? C4 C9 H9A 108.9 . . ? C8A C9 H9A 108.9 . . ? C8B C9 H9A 83.1 . . ? C4 C9 H9B 108.9 . . ? C8A C9 H9B 108.9 . . ? C8B C9 H9B 128.2 . . ? H9A C9 H9B 107.7 . . ? C4 C9 H9C 108.4 . . ? C8A C9 H9C 130.2 . . ? C8B C9 H9C 108.6 . . ? H9A C9 H9C 29.0 . . ? H9B C9 H9C 81.1 . . ? C4 C9 H9D 108.4 . . ? C8A C9 H9D 84.3 . . ? C8B C9 H9D 108.8 . . ? H9A C9 H9D 130.5 . . ? H9B C9 H9D 28.1 . . ? H9C C9 H9D 107.5 . . ? C10 O4 H1O4 109.5(11) . . ? O3 C10 O4 122.62(13) . . ? O3 C10 C11 124.83(12) . . ? O4 C10 C11 112.55(12) . . ? C10 C11 C12 114.85(12) . . ? C10 C11 H11A 108.6 . . ? C12 C11 H11A 108.6 . . ? C10 C11 H11B 108.6 . . ? C12 C11 H11B 108.6 . . ? H11A C11 H11B 107.5 . . ? C13 C12 C11 112.68(12) . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12B 109.1 . . ? C11 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 122.38(13) . . ? C14 C13 C18 121.09(13) . . ? C12 C13 C18 116.52(12) . . ? C13 C14 C15 124.70(14) . . ? C13 C14 H14 117.6 . . ? C15 C14 H14 117.6 . . ? C14 C15 C16 112.03(13) . . ? C14 C15 H15A 109.2 . . ? C16 C15 H15A 109.2 . . ? C14 C15 H15B 109.2 . . ? C16 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C15 C16 C17 110.15(13) . . ? C15 C16 H16A 109.6 . . ? C17 C16 H16A 109.6 . . ? C15 C16 H16B 109.6 . . ? C17 C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? C16 C17 C18 110.46(12) . . ? C16 C17 H17A 109.6 . . ? C18 C17 H17A 109.6 . . ? C16 C17 H17B 109.6 . . ? C18 C17 H17B 109.6 . . ? H17A C17 H17B 108.1 . . ? C13 C18 C17 112.54(12) . . ? C13 C18 H18A 109.1 . . ? C17 C18 H18A 109.1 . . ? C13 C18 H18B 109.1 . . ? C17 C18 H18B 109.1 . . ? H18A C18 H18B 107.8 . . ? C19 O6 H1O6 109.2(13) . . ? O5 C19 O6 122.78(12) . . ? O5 C19 C20 123.27(12) . . ? O6 C19 C20 113.94(12) . . ? C19 C20 C21 113.23(11) . . ? C19 C20 H20A 108.9 . . ? C21 C20 H20A 108.9 . . ? C19 C20 H20B 108.9 . . ? C21 C20 H20B 108.9 . . ? H20A C20 H20B 107.7 . . ? C22 C21 C20 113.43(11) . . ? C22 C21 H21A 108.9 . . ? C20 C21 H21A 108.9 . . ? C22 C21 H21B 108.9 . . ? C20 C21 H21B 108.9 . . ? H21A C21 H21B 107.7 . . ? C23 C22 C21 122.32(13) . . ? C23 C22 C27 121.03(13) . . ? C21 C22 C27 116.62(12) . . ? C22 C23 C24 124.80(14) . . ? C22 C23 H23 117.6 . . ? C24 C23 H23 117.6 . . ? C23 C24 C25 112.10(12) . . ? C23 C24 H24A 109.2 . . ? C25 C24 H24A 109.2 . . ? C23 C24 H24B 109.2 . . ? C25 C24 H24B 109.2 . . ? H24A C24 H24B 107.9 . . ? C26 C25 C24 110.58(12) . . ? C26 C25 H25A 109.5 . . ? C24 C25 H25A 109.5 . . ? C26 C25 H25B 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 108.1 . . ? C25 C26 C27 109.79(12) . . ? C25 C26 H26A 109.7 . . ? C27 C26 H26A 109.7 . . ? C25 C26 H26B 109.7 . . ? C27 C26 H26B 109.7 . . ? H26A C26 H26B 108.2 . . ? C22 C27 C26 112.86(12) . . ? C22 C27 H27A 109.0 . . ? C26 C27 H27A 109.0 . . ? C22 C27 H27B 109.0 . . ? C26 C27 H27B 109.0 . . ? H27A C27 H27B 107.8 . . ? 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 O1 C1 C2 C3 -9.63(19) . . . . ? O2 C1 C2 C3 170.81(11) . . . . ? C1 C2 C3 C4 173.24(11) . . . . ? C2 C3 C4 C5 3.9(2) . . . . ? C2 C3 C4 C9 -175.20(12) . . . . ? C3 C4 C5 C6 -177.49(13) . . . . ? C9 C4 C5 C6 1.6(2) . . . . ? C4 C5 C6 C7A 14.6(2) . . . . ? C4 C5 C6 C7B -16.2(8) . . . . ? C5 C6 C7A C8A -45.3(3) . . . . ? C7B C6 C7A C8A 48.2(12) . . . . ? C6 C7A C8A C9 61.1(3) . . . . ? C5 C6 C7B C8B 46.1(18) . . . . ? C7A C6 C7B C8B -52.1(14) . . . . ? C6 C7B C8B C9 -60(2) . . . . ? C5 C4 C9 C8A 14.0(2) . . . . ? C3 C4 C9 C8A -166.79(15) . . . . ? C5 C4 C9 C8B -16.2(9) . . . . ? C3 C4 C9 C8B 162.9(9) . . . . ? C7A C8A C9 C4 -44.9(3) . . . . ? C7A C8A C9 C8B 54.7(15) . . . . ? C7B C8B C9 C4 45(2) . . . . ? C7B C8B C9 C8A -47.6(13) . . . . ? O3 C10 C11 C12 1.6(2) . . . . ? O4 C10 C11 C12 -177.63(12) . . . . ? C10 C11 C12 C13 178.41(12) . . . . ? C11 C12 C13 C14 -126.15(15) . . . . ? C11 C12 C13 C18 55.08(17) . . . . ? C12 C13 C14 C15 -179.42(15) . . . . ? C18 C13 C14 C15 -0.7(2) . . . . ? C13 C14 C15 C16 -13.6(2) . . . . ? C14 C15 C16 C17 44.15(19) . . . . ? C15 C16 C17 C18 -62.38(16) . . . . ? C14 C13 C18 C17 -16.63(19) . . . . ? C12 C13 C18 C17 162.15(12) . . . . ? C16 C17 C18 C13 47.63(17) . . . . ? O5 C19 C20 C21 11.29(19) . . . . ? O6 C19 C20 C21 -169.25(12) . . . . ? C19 C20 C21 C22 177.14(11) . . . . ? C20 C21 C22 C23 123.62(15) . . . . ? C20 C21 C22 C27 -58.38(16) . . . . ? C21 C22 C23 C24 178.22(13) . . . . ? C27 C22 C23 C24 0.3(2) . . . . ? C22 C23 C24 C25 12.7(2) . . . . ? C23 C24 C25 C26 -43.29(17) . . . . ? C24 C25 C26 C27 61.84(16) . . . . ? C23 C22 C27 C26 17.93(19) . . . . ? C21 C22 C27 C26 -160.10(12) . . . . ? C25 C26 C27 C22 -48.34(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H1O2 O1 0.94(2) 1.72(2) 2.6602(13) 174.6(18) 2_857 O4 H1O4 O5 0.96(2) 1.65(2) 2.6062(14) 174.0(18) 1_656 O6 H1O6 O3 0.95(2) 1.73(2) 2.6735(14) 173.8(19) 1_454 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.17 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.170 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.033 # Attachment 'eva45.cif' data_eva45 _database_code_depnum_ccdc_archive 'CCDC 707950' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H22 N, Cl, H2 O' _chemical_formula_sum 'C16 H24 Cl N O' _chemical_formula_weight 281.81 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' O O 0.0106 0.0060 '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 10.3845(9) _cell_length_b 14.8703(13) _cell_length_c 10.5114(9) _cell_angle_alpha 90.00 _cell_angle_beta 107.902(2) _cell_angle_gamma 90.00 _cell_volume 1544.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5871 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 25.94 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.241 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8285 _exptl_absorpt_correction_T_max 0.8892 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.033 before and 0.017 after correction. The Ratio of minimum to maximum transmission is 0.931699. The \l/2 correction factor is 0.0015 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26250 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0096 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 26.02 _reflns_number_total 3029 _reflns_number_gt 2730 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0933P)^2^+0.3592P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3029 _refine_ls_number_parameters 177 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1540 _refine_ls_wR_factor_gt 0.1499 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _refine_ls_shift/su_max 0.001 _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 0.00394(18) 0.22074(14) 0.3450(2) 0.0547(5) Uani 1 1 d . . . H1A H -0.0545 0.2088 0.2550 0.066 Uiso 1 1 calc R . . H1B H 0.0202 0.1646 0.3944 0.066 Uiso 1 1 calc R . . C2 C -0.06119(18) 0.28800(14) 0.4131(2) 0.0561(5) Uani 1 1 d . . . H2A H -0.1356 0.3186 0.3486 0.067 Uiso 1 1 calc R . . H2B H -0.0949 0.2589 0.4790 0.067 Uiso 1 1 calc R . . C3 C 0.04965(17) 0.35218(12) 0.47795(18) 0.0451(4) Uani 1 1 d . . . C4 C 0.0759(2) 0.39279(13) 0.59525(19) 0.0555(5) Uani 1 1 d . . . H4 H 0.0165 0.3840 0.6447 0.067 Uiso 1 1 calc R . . C5 C 0.1957(2) 0.45188(14) 0.6523(2) 0.0622(5) Uani 1 1 d . . . H5A H 0.2589 0.4220 0.7281 0.075 Uiso 1 1 calc R . . H5B H 0.1668 0.5072 0.6840 0.075 Uiso 1 1 calc R . . C6 C 0.2665(2) 0.47391(14) 0.5494(2) 0.0602(5) Uani 1 1 d . . . H6A H 0.3556 0.4981 0.5946 0.072 Uiso 1 1 calc R . . H6B H 0.2154 0.5198 0.4892 0.072 Uiso 1 1 calc R . . C7 C 0.28113(18) 0.39150(14) 0.4683(2) 0.0527(4) Uani 1 1 d . . . H7A H 0.3300 0.4074 0.4063 0.063 Uiso 1 1 calc R . . H7B H 0.3315 0.3449 0.5275 0.063 Uiso 1 1 calc R . . C8 C 0.14133(17) 0.35757(11) 0.39217(17) 0.0416(4) Uani 1 1 d . . . H8 H 0.1009 0.3978 0.3166 0.050 Uiso 1 1 calc R . . N N 0.13733(13) 0.26147(10) 0.34087(13) 0.0414(3) Uani 1 1 d . . . H1N H 0.199(2) 0.2332(13) 0.398(2) 0.044(5) Uiso 1 1 d . . . Cl Cl 0.32930(5) 0.13344(3) 0.55064(5) 0.0574(2) Uani 1 1 d . . . C9 C 0.15682(17) 0.25114(14) 0.20441(16) 0.0499(4) Uani 1 1 d . . . H9 H 0.0781 0.2782 0.1387 0.060 Uiso 1 1 calc R . . C10 C 0.1598(2) 0.15202(16) 0.1691(2) 0.0674(6) Uani 1 1 d . . . H10A H 0.1710 0.1464 0.0821 0.101 Uiso 1 1 calc R . . H10B H 0.0763 0.1241 0.1687 0.101 Uiso 1 1 calc R . . H10C H 0.2338 0.1230 0.2341 0.101 Uiso 1 1 calc R . . C11 C 0.28125(18) 0.30060(13) 0.19584(17) 0.0490(4) Uani 1 1 d . . . C12 C 0.2662(3) 0.37520(15) 0.1147(2) 0.0657(6) Uani 1 1 d . . . H12 H 0.1798 0.3950 0.0675 0.079 Uiso 1 1 calc R . . C13 C 0.3767(3) 0.42073(18) 0.1023(3) 0.0827(7) Uani 1 1 d . . . H13 H 0.3648 0.4713 0.0478 0.099 Uiso 1 1 calc R . . C14 C 0.5052(3) 0.3914(2) 0.1707(3) 0.0838(8) Uani 1 1 d . . . H14 H 0.5802 0.4218 0.1619 0.101 Uiso 1 1 calc R . . C15 C 0.5222(2) 0.31748(19) 0.2515(3) 0.0723(7) Uani 1 1 d . . . H15 H 0.6091 0.2978 0.2974 0.087 Uiso 1 1 calc R . . C16 C 0.41080(18) 0.27134(15) 0.2655(2) 0.0557(5) Uani 1 1 d . . . H16 H 0.4230 0.2213 0.3211 0.067 Uiso 1 1 calc R . . O O 0.4726(3) 0.03867(17) 0.3461(2) 0.1156(8) Uani 1 1 d . . . H1O H 0.4322 0.0672 0.4074 0.173 Uiso 1 1 d R . . H2O H 0.5410 -0.0024 0.3942 0.173 Uiso 1 1 d 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 C1 0.0439(9) 0.0644(11) 0.0567(10) -0.0049(9) 0.0169(8) -0.0115(8) C2 0.0419(9) 0.0694(12) 0.0607(11) 0.0078(9) 0.0213(8) 0.0001(8) C3 0.0422(8) 0.0485(9) 0.0492(9) 0.0083(7) 0.0206(7) 0.0082(7) C4 0.0664(12) 0.0538(10) 0.0566(11) 0.0051(8) 0.0338(9) 0.0096(9) C5 0.0788(14) 0.0540(11) 0.0577(11) -0.0092(9) 0.0268(10) 0.0061(9) C6 0.0641(12) 0.0517(10) 0.0678(12) -0.0106(9) 0.0246(10) -0.0073(9) C7 0.0463(9) 0.0582(10) 0.0568(10) -0.0108(8) 0.0206(8) -0.0063(8) C8 0.0410(8) 0.0451(9) 0.0406(8) 0.0031(6) 0.0157(7) 0.0034(6) N 0.0338(7) 0.0495(8) 0.0388(7) -0.0005(6) 0.0080(6) 0.0012(6) Cl 0.0537(3) 0.0564(3) 0.0566(3) 0.00528(19) 0.0087(2) 0.00289(18) C9 0.0394(8) 0.0698(11) 0.0389(8) -0.0035(8) 0.0099(7) 0.0091(8) C10 0.0541(11) 0.0758(14) 0.0692(13) -0.0263(11) 0.0142(10) -0.0018(10) C11 0.0495(9) 0.0591(10) 0.0432(9) -0.0034(7) 0.0213(7) 0.0093(8) C12 0.0788(14) 0.0703(13) 0.0564(12) 0.0064(9) 0.0331(11) 0.0188(11) C13 0.120(2) 0.0675(14) 0.0797(16) -0.0004(12) 0.0585(16) -0.0030(14) C14 0.102(2) 0.0836(17) 0.0885(17) -0.0301(14) 0.0622(16) -0.0361(15) C15 0.0494(11) 0.0925(17) 0.0797(15) -0.0274(13) 0.0269(10) -0.0072(11) C16 0.0449(9) 0.0652(12) 0.0597(11) -0.0065(9) 0.0200(8) 0.0048(8) O 0.131(2) 0.1107(17) 0.1165(17) 0.0196(14) 0.0549(15) 0.0268(14) _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 1.506(3) . ? C1 N 1.525(2) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.489(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.324(3) . ? C3 C8 1.501(2) . ? C4 C5 1.490(3) . ? C4 H4 0.9300 . ? C5 C6 1.519(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.527(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.513(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N 1.524(2) . ? C8 H8 0.9800 . ? N C9 1.517(2) . ? N H1N 0.85(2) . ? C9 C11 1.513(3) . ? C9 C10 1.523(3) . ? C9 H9 0.9800 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.379(3) . ? C11 C16 1.389(3) . ? C12 C13 1.372(4) . ? C12 H12 0.9300 . ? C13 C14 1.378(4) . ? C13 H13 0.9300 . ? C14 C15 1.367(4) . ? C14 H14 0.9300 . ? C15 C16 1.392(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? O H1O 0.9677 . ? O H2O 0.9550 . ? 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 N 107.12(15) . . ? C2 C1 H1A 110.3 . . ? N C1 H1A 110.3 . . ? C2 C1 H1B 110.3 . . ? N C1 H1B 110.3 . . ? H1A C1 H1B 108.5 . . ? C3 C2 C1 104.27(14) . . ? C3 C2 H2A 110.9 . . ? C1 C2 H2A 110.9 . . ? C3 C2 H2B 110.9 . . ? C1 C2 H2B 110.9 . . ? H2A C2 H2B 108.9 . . ? C4 C3 C2 128.89(17) . . ? C4 C3 C8 123.22(17) . . ? C2 C3 C8 107.61(15) . . ? C3 C4 C5 123.45(17) . . ? C3 C4 H4 118.3 . . ? C5 C4 H4 118.3 . . ? C4 C5 C6 111.58(17) . . ? C4 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? C4 C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? C5 C6 C7 112.18(17) . . ? C5 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? C5 C6 H6B 109.2 . . ? C7 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C8 C7 C6 108.60(15) . . ? C8 C7 H7A 110.0 . . ? C6 C7 H7A 110.0 . . ? C8 C7 H7B 110.0 . . ? C6 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? C3 C8 C7 112.52(14) . . ? C3 C8 N 102.07(13) . . ? C7 C8 N 114.67(13) . . ? C3 C8 H8 109.1 . . ? C7 C8 H8 109.1 . . ? N C8 H8 109.1 . . ? C9 N C8 115.64(14) . . ? C9 N C1 111.91(13) . . ? C8 N C1 106.78(13) . . ? C9 N H1N 109.3(13) . . ? C8 N H1N 106.3(13) . . ? C1 N H1N 106.3(13) . . ? C11 C9 N 111.82(14) . . ? C11 C9 C10 111.99(15) . . ? N C9 C10 110.31(17) . . ? C11 C9 H9 107.5 . . ? N C9 H9 107.5 . . ? C10 C9 H9 107.5 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 119.04(19) . . ? C12 C11 C9 119.44(17) . . ? C16 C11 C9 121.50(17) . . ? C13 C12 C11 121.1(2) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 119.9(2) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C15 C14 C13 119.9(2) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.6(2) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C11 C16 C15 119.4(2) . . ? C11 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? H1O O H2O 109.4 . . ? 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 N C1 C2 C3 -14.9(2) . . . . ? C1 C2 C3 C4 -142.3(2) . . . . ? C1 C2 C3 C8 31.80(19) . . . . ? C2 C3 C4 C5 176.33(18) . . . . ? C8 C3 C4 C5 3.0(3) . . . . ? C3 C4 C5 C6 11.1(3) . . . . ? C4 C5 C6 C7 -43.7(2) . . . . ? C5 C6 C7 C8 62.0(2) . . . . ? C4 C3 C8 C7 15.7(2) . . . . ? C2 C3 C8 C7 -158.82(15) . . . . ? C4 C3 C8 N 139.11(17) . . . . ? C2 C3 C8 N -35.41(17) . . . . ? C6 C7 C8 C3 -46.3(2) . . . . ? C6 C7 C8 N -162.37(15) . . . . ? C3 C8 N C9 150.29(13) . . . . ? C7 C8 N C9 -87.76(17) . . . . ? C3 C8 N C1 25.06(16) . . . . ? C7 C8 N C1 147.01(15) . . . . ? C2 C1 N C9 -134.08(16) . . . . ? C2 C1 N C8 -6.61(19) . . . . ? C8 N C9 C11 51.03(19) . . . . ? C1 N C9 C11 173.58(15) . . . . ? C8 N C9 C10 176.35(14) . . . . ? C1 N C9 C10 -61.09(19) . . . . ? N C9 C11 C12 -111.66(18) . . . . ? C10 C9 C11 C12 123.94(19) . . . . ? N C9 C11 C16 69.9(2) . . . . ? C10 C9 C11 C16 -54.5(2) . . . . ? C16 C11 C12 C13 -0.2(3) . . . . ? C9 C11 C12 C13 -178.71(19) . . . . ? C11 C12 C13 C14 0.7(3) . . . . ? C12 C13 C14 C15 -0.5(4) . . . . ? C13 C14 C15 C16 0.0(4) . . . . ? C12 C11 C16 C15 -0.3(3) . . . . ? C9 C11 C16 C15 178.11(17) . . . . ? C14 C15 C16 C11 0.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N H1N Cl 0.85(2) 2.29(2) 3.1238(15) 167.1(18) . O H1O Cl 0.97 2.32 3.285(2) 178.3 . O H2O Cl 0.95 2.34 3.254(2) 160.4 3_656 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.300 _refine_diff_density_min -0.525 _refine_diff_density_rms 0.056 # Attachment 'eva46.cif' data_eva46 _database_code_depnum_ccdc_archive 'CCDC 707951' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H24 N, Cl' _chemical_formula_sum 'C17 H24 N Cl' _chemical_formula_weight 277.82 _chemical_absolute_configuration ad 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 'C 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 16.115(2) _cell_length_b 10.4898(13) _cell_length_c 10.9685(14) _cell_angle_alpha 90.00 _cell_angle_beta 121.095(3) _cell_angle_gamma 90.00 _cell_volume 1587.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1106 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 19.24 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.229 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8410 _exptl_absorpt_correction_T_max 0.9665 _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) for selected reflections was 0.037 before and 0.028 after correction. The Ratio of minimum to maximum transmission is 0.870192. The \l/2 correction factor is 0.0015 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4287 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0425 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 20.81 _reflns_number_total 1664 _reflns_number_gt 1444 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0584P)^2^+0.3286P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(10) _refine_ls_number_reflns 1664 _refine_ls_number_parameters 173 _refine_ls_number_restraints 48 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1045 _refine_ls_wR_factor_gt 0.1006 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _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 N N 0.8913(2) 0.2486(3) 0.1573(3) 0.0492(9) Uani 1 1 d U . . H1N H 0.8478 0.2816 0.0705 0.059 Uiso 1 1 calc R . . C1 C 0.9467(3) 0.3598(5) 0.2481(4) 0.0684(12) Uani 1 1 d U . . H1 H 0.9980 0.3264 0.3398 0.082 Uiso 1 1 calc R . . C2 C 0.9943(4) 0.4324(5) 0.1836(7) 0.0992(19) Uani 1 1 d U . . H2A H 1.0486 0.3833 0.1940 0.119 Uiso 1 1 calc R . . H2B H 0.9485 0.4432 0.0825 0.119 Uiso 1 1 calc R . . C3 C 1.0297(5) 0.5602(7) 0.2498(11) 0.165(4) Uani 1 1 d U . . H3A H 1.0591 0.6039 0.2036 0.198 Uiso 1 1 calc R . . H3B H 1.0785 0.5503 0.3498 0.198 Uiso 1 1 calc R . . C4 C 0.9438(5) 0.6398(6) 0.2343(10) 0.153(3) Uani 1 1 d U . . H4A H 0.9687 0.7134 0.2966 0.184 Uiso 1 1 calc R . . H4B H 0.9050 0.6703 0.1372 0.184 Uiso 1 1 calc R . . C5 C 0.8829(5) 0.5650(7) 0.2699(8) 0.122(2) Uani 1 1 d U . . H5 H 0.8418 0.6109 0.2896 0.146 Uiso 1 1 calc R . . C6 C 0.8795(4) 0.4448(5) 0.2772(5) 0.0823(15) Uani 1 1 d U . . C7 C 0.8137(4) 0.3749(7) 0.3125(6) 0.1006(17) Uani 1 1 d U . . H7A H 0.8517 0.3396 0.4077 0.121 Uiso 1 1 calc R . . H7B H 0.7675 0.4345 0.3122 0.121 Uiso 1 1 calc R . . C8 C 0.7616(4) 0.2733(5) 0.2131(5) 0.0775(14) Uani 1 1 d U . . H8A H 0.7192 0.3086 0.1190 0.093 Uiso 1 1 calc R . . H8B H 0.7220 0.2282 0.2420 0.093 Uiso 1 1 calc R . . C9 C 0.8320(3) 0.1832(5) 0.2091(5) 0.0655(13) Uani 1 1 d U . . H9A H 0.7970 0.1124 0.1464 0.079 Uiso 1 1 calc R . . H9B H 0.8748 0.1492 0.3037 0.079 Uiso 1 1 calc R . . C10 C 0.9529(3) 0.1549(4) 0.1311(4) 0.0460(10) Uani 1 1 d U . . H10 H 0.9826 0.2035 0.0872 0.055 Uiso 1 1 calc R . . C11 C 0.8883(3) 0.0551(4) 0.0232(4) 0.0586(12) Uani 1 1 d U . . H11A H 0.9253 0.0071 -0.0070 0.088 Uiso 1 1 calc R . . H11B H 0.8353 0.0965 -0.0576 0.088 Uiso 1 1 calc R . . H11C H 0.8636 -0.0012 0.0660 0.088 Uiso 1 1 calc R . . C12 C 1.0350(3) 0.1006(4) 0.2684(4) 0.0449(11) Uani 1 1 d U . . C13 C 1.1278(3) 0.1508(4) 0.3259(4) 0.0534(11) Uani 1 1 d U . . H13 H 1.1379 0.2171 0.2786 0.064 Uiso 1 1 calc R . . C14 C 1.2051(3) 0.1052(5) 0.4507(5) 0.0638(13) Uani 1 1 d U . . H14 H 1.2662 0.1412 0.4877 0.077 Uiso 1 1 calc R . . C15 C 1.1915(4) 0.0069(5) 0.5200(5) 0.0675(13) Uani 1 1 d U . . H15 H 1.2431 -0.0231 0.6056 0.081 Uiso 1 1 calc R . . C16 C 1.1012(4) -0.0479(5) 0.4629(5) 0.0667(13) Uani 1 1 d U . . H16 H 1.0922 -0.1166 0.5085 0.080 Uiso 1 1 calc R . . C17 C 1.0238(3) -0.0010(4) 0.3378(5) 0.0584(12) Uani 1 1 d U . . H17 H 0.9632 -0.0388 0.2999 0.070 Uiso 1 1 calc R . . Cl Cl 0.76382(8) 0.35672(10) -0.14270(10) 0.0640(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 N 0.047(2) 0.049(2) 0.0377(19) 0.0007(16) 0.0119(17) 0.0048(17) C1 0.053(2) 0.051(2) 0.063(3) -0.004(3) 0.003(2) 0.012(3) C2 0.056(3) 0.049(3) 0.143(5) 0.005(3) 0.017(3) -0.009(3) C3 0.075(4) 0.063(4) 0.275(10) -0.008(5) 0.034(5) -0.010(3) C4 0.094(5) 0.059(4) 0.238(10) -0.017(5) 0.037(5) -0.004(3) C5 0.082(4) 0.073(4) 0.148(6) -0.044(4) 0.016(4) 0.002(4) C6 0.061(3) 0.059(3) 0.067(3) -0.020(3) -0.010(3) 0.020(3) C7 0.095(4) 0.116(5) 0.084(4) -0.011(4) 0.042(3) 0.033(4) C8 0.081(4) 0.091(4) 0.076(4) 0.010(3) 0.052(3) 0.021(3) C9 0.071(3) 0.073(3) 0.068(3) 0.021(3) 0.047(3) 0.016(3) C10 0.046(2) 0.056(3) 0.039(2) 0.005(2) 0.024(2) 0.004(2) C11 0.059(3) 0.060(3) 0.055(3) -0.007(2) 0.028(2) -0.004(2) C12 0.045(3) 0.054(3) 0.041(2) 0.005(2) 0.025(2) 0.011(2) C13 0.048(3) 0.062(3) 0.051(3) 0.002(2) 0.026(2) 0.007(2) C14 0.043(3) 0.084(3) 0.057(3) 0.005(3) 0.021(2) 0.014(2) C15 0.059(3) 0.085(4) 0.052(3) 0.010(3) 0.024(3) 0.032(3) C16 0.076(3) 0.071(3) 0.062(3) 0.024(2) 0.042(3) 0.027(3) C17 0.063(3) 0.059(3) 0.057(3) 0.013(2) 0.033(2) 0.007(2) Cl 0.0665(7) 0.0647(7) 0.0491(6) 0.0123(7) 0.0216(5) 0.0099(7) _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 N C1 1.494(6) . ? N C9 1.506(5) . ? N C10 1.526(5) . ? N H1N 0.9100 . ? C1 C2 1.494(7) . ? C1 C6 1.558(7) . ? C1 H1 0.9800 . ? C2 C3 1.490(9) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.549(10) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.458(10) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.266(8) . ? C5 H5 0.9300 . ? C6 C7 1.496(8) . ? C7 C8 1.443(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.495(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C12 1.511(5) . ? C10 C11 1.519(5) . ? C10 H10 0.9800 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C17 1.375(5) . ? C12 C13 1.392(5) . ? C13 C14 1.375(6) . ? C13 H13 0.9300 . ? C14 C15 1.364(7) . ? C14 H14 0.9300 . ? C15 C16 1.379(7) . ? C15 H15 0.9300 . ? C16 C17 1.383(6) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? 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 N C9 112.4(3) . . ? C1 N C10 114.0(3) . . ? C9 N C10 112.2(3) . . ? C1 N H1N 105.8 . . ? C9 N H1N 105.8 . . ? C10 N H1N 105.8 . . ? C2 C1 N 111.0(4) . . ? C2 C1 C6 112.8(5) . . ? N C1 C6 110.1(3) . . ? C2 C1 H1 107.6 . . ? N C1 H1 107.6 . . ? C6 C1 H1 107.6 . . ? C3 C2 C1 112.8(6) . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C4 109.6(5) . . ? C2 C3 H3A 109.7 . . ? C4 C3 H3A 109.7 . . ? C2 C3 H3B 109.7 . . ? C4 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? C5 C4 C3 111.6(6) . . ? C5 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? C5 C4 H4B 109.3 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? C6 C5 C4 127.6(7) . . ? C6 C5 H5 116.2 . . ? C4 C5 H5 116.2 . . ? C5 C6 C7 124.4(7) . . ? C5 C6 C1 119.9(7) . . ? C7 C6 C1 115.7(5) . . ? C8 C7 C6 112.3(4) . . ? C8 C7 H7A 109.1 . . ? C6 C7 H7A 109.1 . . ? C8 C7 H7B 109.1 . . ? C6 C7 H7B 109.1 . . ? H7A C7 H7B 107.9 . . ? C7 C8 C9 109.6(4) . . ? C7 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? C7 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C8 C9 N 111.2(4) . . ? C8 C9 H9A 109.4 . . ? N C9 H9A 109.4 . . ? C8 C9 H9B 109.4 . . ? N C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C12 C10 C11 114.3(3) . . ? C12 C10 N 112.1(3) . . ? C11 C10 N 109.9(3) . . ? C12 C10 H10 106.7 . . ? C11 C10 H10 106.7 . . ? N C10 H10 106.7 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C17 C12 C13 117.4(4) . . ? C17 C12 C10 123.1(4) . . ? C13 C12 C10 119.5(4) . . ? C14 C13 C12 121.8(4) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C15 C14 C13 119.7(5) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 119.8(5) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C15 C16 C17 120.1(5) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C12 C17 C16 121.1(4) . . ? C12 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? 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 C9 N C1 C2 -172.7(4) . . . . ? C10 N C1 C2 58.2(5) . . . . ? C9 N C1 C6 -47.0(5) . . . . ? C10 N C1 C6 -176.1(4) . . . . ? N C1 C2 C3 166.0(4) . . . . ? C6 C1 C2 C3 41.8(6) . . . . ? C1 C2 C3 C4 -58.6(8) . . . . ? C2 C3 C4 C5 45.2(10) . . . . ? C3 C4 C5 C6 -17.7(11) . . . . ? C4 C5 C6 C7 -179.1(7) . . . . ? C4 C5 C6 C1 0.8(10) . . . . ? C2 C1 C6 C5 -12.3(7) . . . . ? N C1 C6 C5 -136.9(5) . . . . ? C2 C1 C6 C7 167.6(4) . . . . ? N C1 C6 C7 43.0(5) . . . . ? C5 C6 C7 C8 131.0(6) . . . . ? C1 C6 C7 C8 -48.9(6) . . . . ? C6 C7 C8 C9 57.0(6) . . . . ? C7 C8 C9 N -62.4(5) . . . . ? C1 N C9 C8 58.5(5) . . . . ? C10 N C9 C8 -171.5(3) . . . . ? C1 N C10 C12 59.0(4) . . . . ? C9 N C10 C12 -70.3(4) . . . . ? C1 N C10 C11 -172.8(3) . . . . ? C9 N C10 C11 58.0(4) . . . . ? C11 C10 C12 C17 -42.8(5) . . . . ? N C10 C12 C17 83.1(4) . . . . ? C11 C10 C12 C13 134.3(4) . . . . ? N C10 C12 C13 -99.8(4) . . . . ? C17 C12 C13 C14 -2.9(6) . . . . ? C10 C12 C13 C14 179.8(4) . . . . ? C12 C13 C14 C15 0.9(6) . . . . ? C13 C14 C15 C16 1.5(7) . . . . ? C14 C15 C16 C17 -1.9(7) . . . . ? C13 C12 C17 C16 2.5(6) . . . . ? C10 C12 C17 C16 179.7(4) . . . . ? C15 C16 C17 C12 -0.2(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N H1N Cl 0.91 2.16 3.058(3) 170.5 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 20.81 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.192 _refine_diff_density_min -0.112 _refine_diff_density_rms 0.033