# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Koll, A.' 'Filarowski, A.' 'Glowiak, Tadeusz' _publ_contact_author_name 'A. Koll' _publ_contact_author_address ; Contact Address Department of Chemistry University of Wroclaw POLAND ; _publ_contact_author_email 'AKOLL@WCHUWR.CHEM.UNI.WROC.PL' _publ_section_title ; Low barrier hydrogen bonds in sterically modified Schiff bases ; data_tium3 _database_code_CSD 168009 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 Cl N O' _chemical_formula_weight 183.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.3639 0.7018 '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 6.4110(10) _cell_length_b 7.2730(10) _cell_length_c 10.251(2) _cell_angle_alpha 99.03(3) _cell_angle_beta 95.57(3) _cell_angle_gamma 105.59(3) _cell_volume 449.79(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12.7 _cell_measurement_theta_max 23.1 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 192 _exptl_absorpt_coefficient_mu 3.349 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Kuma KM4 automatic diffractometer' _diffrn_measurement_method 'profile data from omega/2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3522 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0402 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.41 _diffrn_reflns_theta_max 80.29 _reflns_number_total 1841 _reflns_number_gt 1411 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma KM4 software 1987' _computing_cell_refinement 'Kuma KM4 software 1987' _computing_data_reduction 'Kuma KM4 software 1987' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0803P)^2^+0.0412P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.081(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1841 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1400 _refine_ls_wR_factor_gt 0.1295 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.21669(11) 0.13594(12) 0.92872(6) 0.0931(3) Uani 1 d . . . O1 O 0.9090(2) 0.3949(3) 0.61204(15) 0.0789(5) Uani 1 d . . . N1 N 0.6298(3) 0.3002(3) 0.40833(15) 0.0593(4) Uani 1 d . . . C1 C 0.7490(3) 0.3406(3) 0.67941(19) 0.0605(5) Uani 1 d . . . C2 C 0.5273(3) 0.2634(3) 0.61826(16) 0.0512(4) Uani 1 d . . . C3 C 0.3653(3) 0.2034(3) 0.69825(19) 0.0583(5) Uani 1 d . . . C4 C 0.4182(3) 0.2198(3) 0.83199(19) 0.0631(5) Uani 1 d . . . C5 C 0.6328(4) 0.2971(4) 0.8930(2) 0.0769(7) Uani 1 d . . . C6 C 0.7934(4) 0.3580(4) 0.8192(2) 0.0790(7) Uani 1 d . . . C7 C 0.4714(3) 0.2446(3) 0.47472(17) 0.0531(4) Uani 1 d . . . C8 C 0.2397(4) 0.1653(4) 0.4089(3) 0.0728(6) Uani 1 d . . . C9 C 0.6069(5) 0.2914(4) 0.2644(2) 0.0739(6) Uani 1 d . . . H1 H 0.773(5) 0.347(5) 0.475(4) 0.107(10) Uiso 1 d . . . H3 H 0.219(4) 0.160(4) 0.660(3) 0.080(8) Uiso 1 d . . . H5 H 0.676(5) 0.309(5) 0.980(4) 0.107(10) Uiso 1 d . . . H6 H 0.949(5) 0.415(4) 0.859(3) 0.084(8) Uiso 1 d . . . H8A H 0.144(6) 0.233(5) 0.448(4) 0.120(12) Uiso 1 d . . . H8B H 0.163(7) 0.042(6) 0.426(4) 0.131(13) Uiso 1 d . . . H8C H 0.221(7) 0.168(7) 0.328(5) 0.150(16) Uiso 1 d . . . H9A H 0.741(6) 0.331(6) 0.255(4) 0.111(12) Uiso 1 d . . . H9B H 0.513(6) 0.367(6) 0.235(4) 0.127(12) Uiso 1 d . . . H9C H 0.510(5) 0.170(5) 0.216(3) 0.100(9) Uiso 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 Cl1 0.0911(5) 0.1197(6) 0.0744(4) 0.0354(3) 0.0362(3) 0.0221(4) O1 0.0490(7) 0.1176(14) 0.0652(8) 0.0259(8) 0.0092(6) 0.0105(7) N1 0.0648(9) 0.0617(11) 0.0483(8) 0.0088(6) 0.0094(7) 0.0136(7) C1 0.0531(9) 0.0730(14) 0.0546(9) 0.0174(8) 0.0050(7) 0.0147(8) C2 0.0527(9) 0.0519(11) 0.0482(8) 0.0103(7) 0.0063(6) 0.0136(7) C3 0.0526(9) 0.0621(12) 0.0577(10) 0.0140(8) 0.0089(7) 0.0109(8) C4 0.0685(11) 0.0662(13) 0.0569(10) 0.0187(8) 0.0161(8) 0.0169(9) C5 0.0776(13) 0.0995(18) 0.0490(10) 0.0206(10) 0.0032(9) 0.0164(12) C6 0.0611(11) 0.109(2) 0.0583(11) 0.0219(11) -0.0018(9) 0.0102(11) C7 0.0571(9) 0.0484(11) 0.0514(9) 0.0075(7) 0.0040(7) 0.0137(7) C8 0.0602(11) 0.0856(18) 0.0611(11) 0.0076(10) -0.0037(9) 0.0097(11) C9 0.0897(17) 0.0828(18) 0.0463(9) 0.0100(9) 0.0112(10) 0.0208(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 Cl1 C4 1.743(2) . ? O1 C1 1.300(2) . ? N1 C7 1.288(2) . ? N1 C9 1.458(3) . ? N1 H1 1.03(3) . ? C1 C6 1.413(3) . ? C1 C2 1.420(3) . ? C2 C3 1.405(3) . ? C2 C7 1.456(2) . ? C3 C4 1.358(3) . ? C3 H3 0.93(3) . ? C4 C5 1.381(3) . ? C5 C6 1.356(3) . ? C5 H5 0.90(4) . ? C6 H6 0.99(3) . ? C7 C8 1.488(3) . ? C8 H8A 0.97(4) . ? C8 H8B 0.95(4) . ? C8 H8C 0.83(5) . ? C9 H9A 0.85(4) . ? C9 H9B 0.97(4) . ? C9 H9C 0.96(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 C9 125.31(19) . . ? C7 N1 H1 107.5(19) . . ? C9 N1 H1 127.2(19) . . ? O1 C1 C6 119.77(18) . . ? O1 C1 C2 122.65(17) . . ? C6 C1 C2 117.59(19) . . ? C3 C2 C1 118.86(16) . . ? C3 C2 C7 121.11(16) . . ? C1 C2 C7 120.02(16) . . ? C4 C3 C2 120.97(18) . . ? C4 C3 H3 119.8(16) . . ? C2 C3 H3 119.1(16) . . ? C3 C4 C5 120.75(19) . . ? C3 C4 Cl1 120.36(16) . . ? C5 C4 Cl1 118.86(15) . . ? C6 C5 C4 119.98(19) . . ? C6 C5 H5 116(2) . . ? C4 C5 H5 124(2) . . ? C5 C6 C1 121.8(2) . . ? C5 C6 H6 122.7(17) . . ? C1 C6 H6 115.5(17) . . ? N1 C7 C2 117.23(16) . . ? N1 C7 C8 121.95(18) . . ? C2 C7 C8 120.82(18) . . ? C7 C8 H8A 113(2) . . ? C7 C8 H8B 115(2) . . ? H8A C8 H8B 95(3) . . ? C7 C8 H8C 114(3) . . ? H8A C8 H8C 105(4) . . ? H8B C8 H8C 111(4) . . ? N1 C9 H9A 100(3) . . ? N1 C9 H9B 112(2) . . ? H9A C9 H9B 117(3) . . ? N1 C9 H9C 112(2) . . ? H9A C9 H9C 123(3) . . ? H9B C9 H9C 94(3) . . ? 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 178.3(2) . . . . ? C6 C1 C2 C3 -1.8(3) . . . . ? O1 C1 C2 C7 -0.8(3) . . . . ? C6 C1 C2 C7 179.1(2) . . . . ? C1 C2 C3 C4 0.5(3) . . . . ? C7 C2 C3 C4 179.5(2) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? C2 C3 C4 Cl1 -177.46(16) . . . . ? C3 C4 C5 C6 0.1(4) . . . . ? Cl1 C4 C5 C6 178.0(2) . . . . ? C4 C5 C6 C1 -1.6(5) . . . . ? O1 C1 C6 C5 -177.7(3) . . . . ? C2 C1 C6 C5 2.4(4) . . . . ? C9 N1 C7 C2 179.5(2) . . . . ? C9 N1 C7 C8 -0.9(3) . . . . ? C3 C2 C7 N1 -178.97(18) . . . . ? C1 C2 C7 N1 0.1(3) . . . . ? C3 C2 C7 C8 1.4(3) . . . . ? C1 C2 C7 C8 -179.6(2) . . . . ? 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 N1 H1 O1 1.03(3) 1.52(4) 2.490(2) 155(3) . _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 80.29 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.245 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.044 data_tium12 _database_code_CSD 168010 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H14 Cl N O' _chemical_formula_weight 211.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.3639 0.7018 '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 6.9530(10) _cell_length_b 7.594(2) _cell_length_c 11.013(2) _cell_angle_alpha 79.12(3) _cell_angle_beta 83.75(3) _cell_angle_gamma 76.06(3) _cell_volume 553.00(19) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 13.4 _cell_measurement_theta_max 24.3 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 2.790 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Kuma KM4 automatic diffractometer' _diffrn_measurement_method 'profile data from omega/2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4528 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.10 _diffrn_reflns_theta_max 80.94 _reflns_number_total 2266 _reflns_number_gt 1942 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma KM4 software 1987' _computing_cell_refinement 'Kuma KM4 software 1987' _computing_data_reduction 'Kuma KM4 software 1987' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0871P)^2^+0.0331P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.079(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2266 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1328 _refine_ls_wR_factor_gt 0.1276 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.15140(6) 0.56188(7) 0.13421(4) 0.0714(2) Uani 1 d . . . O1 O 0.82063(16) 0.2480(2) 0.44558(13) 0.0728(4) Uani 1 d . . . N1 N 0.58644(19) 0.1536(2) 0.61918(12) 0.0555(3) Uani 1 d . . . C1 C 0.6659(2) 0.3138(3) 0.37816(15) 0.0556(4) Uani 1 d . . . C2 C 0.46819(19) 0.3080(2) 0.42739(13) 0.0484(3) Uani 1 d . . . C3 C 0.3116(2) 0.3860(2) 0.35022(13) 0.0509(4) Uani 1 d . . . C4 C 0.3473(2) 0.4640(3) 0.22980(14) 0.0547(4) Uani 1 d . . . C5 C 0.5404(3) 0.4666(3) 0.18031(15) 0.0615(4) Uani 1 d . . . C6 C 0.6952(2) 0.3915(3) 0.25399(16) 0.0657(5) Uani 1 d . . . C7 C 0.4336(2) 0.2219(2) 0.55576(13) 0.0500(4) Uani 1 d . . . C8 C 0.2268(2) 0.2133(4) 0.60837(17) 0.0661(5) Uani 1 d . . . C9 C 0.5779(3) 0.0634(3) 0.74837(15) 0.0590(4) Uani 1 d . . . C10 C 0.7853(3) -0.0069(3) 0.7924(2) 0.0712(5) Uani 1 d . . . C11 C 0.7836(5) -0.0838(5) 0.9296(3) 0.0955(8) Uani 1 d . . . H1 H 0.758(5) 0.205(5) 0.531(4) 0.131(11) Uiso 1 d . . . H2 H 0.172(3) 0.385(3) 0.378(2) 0.077(7) Uiso 1 d . . . H3 H 0.573(3) 0.512(4) 0.104(2) 0.077(6) Uiso 1 d . . . H4 H 0.834(4) 0.387(4) 0.222(2) 0.087(7) Uiso 1 d . . . H5 H 0.168(5) 0.163(6) 0.573(3) 0.135(13) Uiso 1 d . . . H6 H 0.144(4) 0.338(5) 0.595(3) 0.101(9) Uiso 1 d . . . H7 H 0.224(4) 0.165(5) 0.691(3) 0.108(9) Uiso 1 d . . . H8 H 0.507(3) 0.153(3) 0.7955(19) 0.066(6) Uiso 1 d . . . H9 H 0.514(3) -0.042(3) 0.7642(19) 0.060(5) Uiso 1 d . . . H10 H 0.857(3) 0.089(4) 0.766(2) 0.079(7) Uiso 1 d . . . H11 H 0.858(4) -0.105(4) 0.743(3) 0.096(8) Uiso 1 d . . . H12 H 0.914(6) -0.126(6) 0.963(4) 0.146(13) Uiso 1 d . . . H13 H 0.705(5) -0.169(5) 0.951(3) 0.107(10) Uiso 1 d . . . H14 H 0.719(4) 0.013(4) 0.969(3) 0.091(8) Uiso 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 Cl1 0.0619(3) 0.0868(4) 0.0587(3) 0.0061(2) -0.01130(17) -0.0143(2) O1 0.0419(5) 0.1095(11) 0.0642(7) -0.0036(7) -0.0035(5) -0.0205(6) N1 0.0498(6) 0.0641(9) 0.0505(7) -0.0046(6) -0.0042(5) -0.0123(5) C1 0.0422(7) 0.0710(11) 0.0557(8) -0.0117(7) 0.0004(5) -0.0176(6) C2 0.0417(6) 0.0568(9) 0.0476(7) -0.0099(6) 0.0014(5) -0.0139(5) C3 0.0427(6) 0.0590(9) 0.0497(7) -0.0075(6) 0.0011(5) -0.0121(6) C4 0.0511(7) 0.0642(10) 0.0497(7) -0.0075(6) -0.0021(5) -0.0167(6) C5 0.0612(9) 0.0777(12) 0.0479(8) -0.0053(7) 0.0057(6) -0.0281(8) C6 0.0495(8) 0.0919(14) 0.0577(9) -0.0096(8) 0.0085(6) -0.0272(8) C7 0.0446(7) 0.0560(9) 0.0497(7) -0.0106(6) 0.0014(5) -0.0126(5) C8 0.0466(8) 0.0944(15) 0.0537(9) -0.0028(8) 0.0029(6) -0.0190(8) C9 0.0615(9) 0.0621(11) 0.0508(8) -0.0044(7) -0.0052(6) -0.0125(7) C10 0.0687(10) 0.0760(14) 0.0678(10) -0.0057(9) -0.0186(8) -0.0131(9) C11 0.1089(19) 0.098(2) 0.0742(14) 0.0078(13) -0.0370(13) -0.0172(17) _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 Cl1 C4 1.7451(17) . ? O1 C1 1.317(2) . ? O1 H1 1.02(4) . ? N1 C7 1.283(2) . ? N1 C9 1.459(2) . ? C1 C6 1.397(2) . ? C1 C2 1.4292(19) . ? C2 C3 1.399(2) . ? C2 C7 1.462(2) . ? C3 C4 1.369(2) . ? C3 H2 0.99(2) . ? C4 C5 1.396(2) . ? C5 C6 1.364(3) . ? C5 H3 0.87(3) . ? C6 H4 0.98(3) . ? C7 C8 1.502(2) . ? C8 H5 0.80(4) . ? C8 H6 0.98(3) . ? C8 H7 0.92(3) . ? C9 C10 1.512(2) . ? C9 H8 0.94(2) . ? C9 H9 0.99(2) . ? C10 C11 1.513(3) . ? C10 H10 0.96(3) . ? C10 H11 1.01(3) . ? C11 H12 0.97(4) . ? C11 H13 0.93(4) . ? C11 H14 0.92(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 103.0(19) . . ? C7 N1 C9 124.04(13) . . ? O1 C1 C6 119.08(14) . . ? O1 C1 C2 122.29(15) . . ? C6 C1 C2 118.62(14) . . ? C3 C2 C1 118.53(14) . . ? C3 C2 C7 121.59(12) . . ? C1 C2 C7 119.88(13) . . ? C4 C3 C2 120.73(13) . . ? C4 C3 H2 116.7(13) . . ? C2 C3 H2 122.6(13) . . ? C3 C4 C5 121.05(15) . . ? C3 C4 Cl1 120.52(12) . . ? C5 C4 Cl1 118.43(13) . . ? C6 C5 C4 119.18(15) . . ? C6 C5 H3 115.6(15) . . ? C4 C5 H3 125.3(15) . . ? C5 C6 C1 121.86(14) . . ? C5 C6 H4 122.0(16) . . ? C1 C6 H4 116.2(16) . . ? N1 C7 C2 117.08(13) . . ? N1 C7 C8 122.46(14) . . ? C2 C7 C8 120.45(13) . . ? C7 C8 H5 116(2) . . ? C7 C8 H6 108.1(18) . . ? H5 C8 H6 100(3) . . ? C7 C8 H7 111.7(18) . . ? H5 C8 H7 110(3) . . ? H6 C8 H7 110(2) . . ? N1 C9 C10 109.99(15) . . ? N1 C9 H8 107.4(14) . . ? C10 C9 H8 108.8(13) . . ? N1 C9 H9 114.6(12) . . ? C10 C9 H9 107.1(12) . . ? H8 C9 H9 108.9(17) . . ? C9 C10 C11 112.0(2) . . ? C9 C10 H10 108.2(14) . . ? C11 C10 H10 115.0(15) . . ? C9 C10 H11 107.6(16) . . ? C11 C10 H11 110.4(17) . . ? H10 C10 H11 103(2) . . ? C10 C11 H12 115(3) . . ? C10 C11 H13 112(2) . . ? H12 C11 H13 113(3) . . ? C10 C11 H14 105.6(18) . . ? H12 C11 H14 106(3) . . ? H13 C11 H14 104(3) . . ? 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 178.16(17) . . . . ? C6 C1 C2 C3 -2.0(3) . . . . ? O1 C1 C2 C7 -1.9(3) . . . . ? C6 C1 C2 C7 177.92(16) . . . . ? C1 C2 C3 C4 0.8(2) . . . . ? C7 C2 C3 C4 -179.19(15) . . . . ? C2 C3 C4 C5 0.6(3) . . . . ? C2 C3 C4 Cl1 -179.72(13) . . . . ? C3 C4 C5 C6 -0.6(3) . . . . ? Cl1 C4 C5 C6 179.66(16) . . . . ? C4 C5 C6 C1 -0.7(3) . . . . ? O1 C1 C6 C5 -178.15(19) . . . . ? C2 C1 C6 C5 2.0(3) . . . . ? C9 N1 C7 C2 179.83(15) . . . . ? C9 N1 C7 C8 -1.0(3) . . . . ? C3 C2 C7 N1 179.76(15) . . . . ? C1 C2 C7 N1 -0.2(2) . . . . ? C3 C2 C7 C8 0.5(3) . . . . ? C1 C2 C7 C8 -179.42(17) . . . . ? C7 N1 C9 C10 177.84(17) . . . . ? N1 C9 C10 C11 174.0(2) . . . . ? 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 O1 H1 N1 1.02(4) 1.53(4) 2.4874(19) 153(3) . _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 80.94 _diffrn_measured_fraction_theta_full 0.931 _refine_diff_density_max 0.456 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.057 data_tium15 _database_code_CSD 168011 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H12 Cl N O' _chemical_formula_weight 197.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 4.8670(10) _cell_length_b 12.082(2) _cell_length_c 16.367(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.35(3) _cell_angle_gamma 90.00 _cell_volume 962.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12.1 _cell_measurement_theta_max 23.8 _exptl_crystal_description ? _exptl_crystal_colour ? _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 1.364 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 3.169 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Kuma KM4 automatic diffractometer' _diffrn_measurement_method 'profile data from omega/2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2228 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.55 _diffrn_reflns_theta_max 80.28 _reflns_number_total 1993 _reflns_number_gt 1525 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma KM4 software 1987' _computing_cell_refinement 'Kuma KM4 software 1987' _computing_data_reduction 'Kuma KM4 software 1987' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0917P)^2^+0.1093P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0097(13) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1993 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1337 _refine_ls_wR_factor_gt 0.1196 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.09755(13) 0.65653(4) 0.44956(3) 0.0604(2) Uani 1 d . . . O1 O -0.3801(3) 0.86381(11) 0.73867(9) 0.0532(4) Uani 1 d . . . N1 N -0.6629(4) 0.69479(15) 0.75948(10) 0.0467(4) Uani 1 d . . . C1 C -0.2761(4) 0.81482(14) 0.67437(11) 0.0385(4) Uani 1 d . . . C2 C -0.3572(4) 0.70614(14) 0.64988(10) 0.0359(4) Uani 1 d . . . C3 C -0.2372(4) 0.66042(14) 0.57983(11) 0.0392(4) Uani 1 d . . . C4 C -0.0430(4) 0.71769(14) 0.53628(11) 0.0388(4) Uani 1 d . . . C5 C 0.0430(4) 0.82426(14) 0.55914(11) 0.0375(4) Uani 1 d . . . C6 C -0.0749(4) 0.86970(14) 0.62776(11) 0.0401(4) Uani 1 d . . . C7 C -0.5623(4) 0.64502(14) 0.69663(11) 0.0393(4) Uani 1 d . . . C8 C 0.2554(5) 0.88666(19) 0.51181(14) 0.0497(5) Uani 1 d . . . C9 C -0.6406(5) 0.53009(17) 0.67197(15) 0.0517(5) Uani 1 d . . . C10 C -0.8688(5) 0.6496(2) 0.81436(16) 0.0585(6) Uani 1 d . . . H1 H -0.560(8) 0.777(3) 0.763(2) 0.116(13) Uiso 1 d . . . H2 H -0.287(5) 0.587(2) 0.5589(14) 0.049(6) Uiso 1 d . . . H3 H -0.027(6) 0.943(2) 0.6474(17) 0.069(8) Uiso 1 d . . . H4 H 0.217(6) 0.889(3) 0.453(2) 0.076(8) Uiso 1 d . . . H5 H 0.280(7) 0.959(3) 0.535(2) 0.095(11) Uiso 1 d . . . H6 H 0.432(10) 0.845(3) 0.512(3) 0.127(16) Uiso 1 d . . . H7 H -0.784(7) 0.502(3) 0.701(2) 0.081(9) Uiso 1 d . . . H8 H -0.486(6) 0.482(2) 0.6827(18) 0.067(8) Uiso 1 d . . . H9 H -0.674(7) 0.525(2) 0.611(2) 0.081(9) Uiso 1 d . . . H10 H -1.002(8) 0.707(3) 0.822(2) 0.089(10) Uiso 1 d . . . H11 H -0.796(8) 0.639(3) 0.860(2) 0.100(12) Uiso 1 d . . . H12 H -0.930(9) 0.580(4) 0.795(3) 0.123(14) Uiso 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 Cl1 0.0728(4) 0.0591(3) 0.0496(3) -0.0120(2) 0.0245(2) -0.0041(2) O1 0.0628(9) 0.0460(7) 0.0510(8) -0.0124(6) 0.0201(6) -0.0054(6) N1 0.0453(10) 0.0497(9) 0.0452(9) 0.0061(7) 0.0122(7) 0.0005(7) C1 0.0414(10) 0.0360(8) 0.0380(8) -0.0015(6) 0.0049(7) 0.0009(6) C2 0.0365(9) 0.0346(8) 0.0367(8) 0.0022(6) 0.0038(6) -0.0003(6) C3 0.0433(11) 0.0353(8) 0.0390(9) -0.0008(6) 0.0046(7) -0.0030(6) C4 0.0400(10) 0.0407(8) 0.0358(8) 0.0003(6) 0.0054(7) 0.0022(6) C5 0.0344(10) 0.0399(8) 0.0381(8) 0.0055(6) 0.0006(6) -0.0008(6) C6 0.0423(11) 0.0351(8) 0.0428(9) -0.0010(6) 0.0027(7) -0.0045(6) C7 0.0358(10) 0.0406(8) 0.0416(9) 0.0083(7) 0.0018(7) -0.0001(6) C8 0.0456(12) 0.0504(11) 0.0533(11) 0.0100(9) 0.0104(9) -0.0052(8) C9 0.0548(13) 0.0427(10) 0.0576(12) 0.0064(9) 0.0067(9) -0.0116(9) C10 0.0515(14) 0.0733(15) 0.0508(12) 0.0158(11) 0.0181(10) 0.0016(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C4 1.7437(18) . ? O1 C1 1.312(2) . ? O1 H1 1.43(4) . ? N1 C7 1.291(2) . ? N1 C10 1.456(3) . ? N1 H1 1.11(4) . ? C1 C6 1.411(2) . ? C1 C2 1.428(2) . ? C2 C3 1.403(2) . ? C2 C7 1.462(2) . ? C3 C4 1.374(2) . ? C3 H2 0.98(2) . ? C4 C5 1.404(2) . ? C5 C6 1.378(2) . ? C5 C8 1.499(3) . ? C6 H3 0.97(3) . ? C7 C9 1.495(3) . ? C8 H4 0.99(3) . ? C8 H5 0.96(4) . ? C8 H6 0.99(5) . ? C9 H7 0.91(4) . ? C9 H8 0.97(3) . ? C9 H9 1.01(3) . ? C10 H10 0.95(4) . ? C10 H11 0.83(4) . ? C10 H12 0.95(5) . ? 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 O1 H1 97.7(16) . . ? C7 N1 C10 125.64(19) . . ? C7 N1 H1 107(2) . . ? C10 N1 H1 128(2) . . ? O1 C1 C6 119.63(16) . . ? O1 C1 C2 122.19(16) . . ? C6 C1 C2 118.18(16) . . ? C3 C2 C1 118.40(15) . . ? C3 C2 C7 121.18(15) . . ? C1 C2 C7 120.42(15) . . ? C4 C3 C2 121.10(16) . . ? C4 C3 H2 116.4(14) . . ? C2 C3 H2 122.5(14) . . ? C3 C4 C5 121.90(16) . . ? C3 C4 Cl1 118.90(14) . . ? C5 C4 Cl1 119.20(14) . . ? C6 C5 C4 117.23(16) . . ? C6 C5 C8 120.83(17) . . ? C4 C5 C8 121.93(17) . . ? C5 C6 C1 123.17(16) . . ? C5 C6 H3 122.2(18) . . ? C1 C6 H3 114.6(17) . . ? N1 C7 C2 116.44(16) . . ? N1 C7 C9 123.42(18) . . ? C2 C7 C9 120.12(17) . . ? C5 C8 H4 113.4(19) . . ? C5 C8 H5 110(2) . . ? H4 C8 H5 112(3) . . ? C5 C8 H6 110(3) . . ? H4 C8 H6 100(3) . . ? H5 C8 H6 111(3) . . ? C7 C9 H7 114(2) . . ? C7 C9 H8 108.0(17) . . ? H7 C9 H8 106(3) . . ? C7 C9 H9 110.9(17) . . ? H7 C9 H9 112(3) . . ? H8 C9 H9 105(2) . . ? N1 C10 H10 106(2) . . ? N1 C10 H11 109(3) . . ? H10 C10 H11 106(3) . . ? N1 C10 H12 110(3) . . ? H10 C10 H12 118(3) . . ? H11 C10 H12 107(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 O1 C1 C2 C3 179.42(17) . . . . ? C6 C1 C2 C3 -1.3(3) . . . . ? O1 C1 C2 C7 -0.1(3) . . . . ? C6 C1 C2 C7 179.21(17) . . . . ? C1 C2 C3 C4 1.0(3) . . . . ? C7 C2 C3 C4 -179.53(17) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C2 C3 C4 Cl1 -179.78(14) . . . . ? C3 C4 C5 C6 0.3(3) . . . . ? Cl1 C4 C5 C6 179.57(14) . . . . ? C3 C4 C5 C8 179.83(19) . . . . ? Cl1 C4 C5 C8 -0.9(3) . . . . ? C4 C5 C6 C1 -0.6(3) . . . . ? C8 C5 C6 C1 179.79(19) . . . . ? O1 C1 C6 C5 -179.53(17) . . . . ? C2 C1 C6 C5 1.2(3) . . . . ? C10 N1 C7 C2 179.9(2) . . . . ? C10 N1 C7 C9 -1.5(3) . . . . ? C3 C2 C7 N1 -179.16(17) . . . . ? C1 C2 C7 N1 0.3(3) . . . . ? C3 C2 C7 C9 2.2(3) . . . . ? C1 C2 C7 C9 -178.31(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 N1 H1 O1 1.11(4) 1.43(4) 2.487(2) 157(4) . _diffrn_measured_fraction_theta_max 0.901 _diffrn_reflns_theta_full 80.28 _diffrn_measured_fraction_theta_full 0.901 _refine_diff_density_max 0.267 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.061 data_tium17 _database_code_CSD 168012 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H14 Cl N O' _chemical_formula_weight 211.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.3639 0.7018 '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 6.9840(10) _cell_length_b 7.515(2) _cell_length_c 11.298(2) _cell_angle_alpha 75.26(3) _cell_angle_beta 79.65(3) _cell_angle_gamma 72.89(3) _cell_volume 544.54(19) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12.4 _cell_measurement_theta_max 24.3 _exptl_crystal_description ? _exptl_crystal_colour ? _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 1.291 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 2.834 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Kuma KM4 automatic diffractometer' _diffrn_measurement_method 'profile data from omega/2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4450 _diffrn_reflns_av_R_equivalents 0.0584 _diffrn_reflns_av_sigmaI/netI 0.0597 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.07 _diffrn_reflns_theta_max 80.27 _reflns_number_total 2229 _reflns_number_gt 1911 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma KM4 software 1987' _computing_cell_refinement 'Kuma KM4 software 1987' _computing_data_reduction 'Kuma KM4 software 1987' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0539P)^2^+0.1248P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0031(11) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2229 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1292 _refine_ls_wR_factor_gt 0.1231 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.003 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.47969(9) 0.16666(9) 0.12075(4) 0.0737(2) Uani 1 d . . . O1 O -0.2914(2) 0.2808(2) 0.43155(12) 0.0611(4) Uani 1 d . . . N1 N -0.1119(2) 0.2697(2) 0.60594(12) 0.0464(3) Uani 1 d . . . C1 C -0.1151(3) 0.2579(2) 0.36412(15) 0.0458(4) Uani 1 d . . . C2 C 0.0666(3) 0.2338(2) 0.41305(13) 0.0406(4) Uani 1 d . . . C3 C 0.2473(3) 0.2053(2) 0.33522(14) 0.0459(4) Uani 1 d . . . C4 C 0.2490(3) 0.2045(2) 0.21334(14) 0.0476(4) Uani 1 d . . . C5 C 0.0726(3) 0.2334(2) 0.16165(15) 0.0500(4) Uani 1 d . . . C6 C -0.1051(3) 0.2597(3) 0.23839(16) 0.0535(4) Uani 1 d . . . C7 C 0.0613(3) 0.2411(2) 0.54208(13) 0.0425(4) Uani 1 d . . . C8 C 0.0748(5) 0.2329(4) 0.02814(19) 0.0714(6) Uani 1 d . . . C9 C 0.2505(4) 0.2197(4) 0.59396(18) 0.0591(5) Uani 1 d . . . C10 C -0.1450(3) 0.2868(3) 0.73460(15) 0.0536(5) Uani 1 d . . . C11 C -0.3661(4) 0.3343(4) 0.7773(2) 0.0737(7) Uani 1 d . . . H1 H -0.229(6) 0.265(5) 0.539(4) 0.134(13) Uiso 1 d . . . H2 H 0.378(4) 0.188(3) 0.367(2) 0.068(7) Uiso 1 d . . . H3 H -0.237(4) 0.283(3) 0.204(2) 0.074(7) Uiso 1 d . . . H4 H 0.147(5) 0.100(5) 0.010(3) 0.105(10) Uiso 1 d . . . H5 H -0.052(5) 0.252(4) 0.012(3) 0.095(10) Uiso 1 d . . . H6 H 0.137(5) 0.332(4) -0.024(3) 0.089(9) Uiso 1 d . . . H7 H 0.237(7) 0.176(6) 0.676(4) 0.156(16) Uiso 1 d . . . H8 H 0.359(7) 0.132(6) 0.568(4) 0.139(14) Uiso 1 d . . . H9 H 0.299(7) 0.320(7) 0.563(4) 0.158(17) Uiso 1 d . . . H10 H -0.082(3) 0.169(3) 0.784(2) 0.058(6) Uiso 1 d . . . H11 H -0.083(3) 0.386(3) 0.7420(19) 0.053(5) Uiso 1 d . . . H12 H -0.438(4) 0.452(4) 0.720(3) 0.088(8) Uiso 1 d . . . H13 H -0.431(4) 0.233(4) 0.776(2) 0.086(9) Uiso 1 d . . . H14 H -0.392(5) 0.361(5) 0.862(3) 0.112(11) Uiso 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 Cl1 0.0624(4) 0.1104(5) 0.0561(3) -0.0371(3) 0.0155(2) -0.0310(3) O1 0.0429(8) 0.0912(10) 0.0519(7) -0.0214(6) -0.0018(5) -0.0185(7) N1 0.0534(9) 0.0509(7) 0.0354(6) -0.0102(5) -0.0025(6) -0.0148(6) C1 0.0446(10) 0.0526(8) 0.0423(7) -0.0121(6) -0.0052(6) -0.0140(7) C2 0.0446(10) 0.0416(7) 0.0367(7) -0.0089(5) -0.0059(6) -0.0116(6) C3 0.0455(10) 0.0510(8) 0.0425(8) -0.0127(6) -0.0045(7) -0.0127(7) C4 0.0511(11) 0.0520(9) 0.0425(8) -0.0159(6) 0.0020(7) -0.0171(7) C5 0.0630(12) 0.0517(9) 0.0396(8) -0.0137(6) -0.0068(7) -0.0175(8) C6 0.0526(12) 0.0669(11) 0.0464(9) -0.0171(7) -0.0118(7) -0.0156(8) C7 0.0504(10) 0.0409(7) 0.0362(7) -0.0067(5) -0.0071(6) -0.0120(6) C8 0.0856(19) 0.0922(17) 0.0432(10) -0.0241(10) -0.0085(10) -0.0246(14) C9 0.0537(13) 0.0804(13) 0.0461(9) -0.0159(9) -0.0123(8) -0.0159(10) C10 0.0706(13) 0.0527(9) 0.0348(7) -0.0090(6) -0.0016(7) -0.0149(8) C11 0.0815(18) 0.0847(15) 0.0517(11) -0.0197(10) 0.0173(10) -0.0271(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 Cl1 C4 1.7459(19) . ? O1 C1 1.316(2) . ? O1 H1 1.33(4) . ? N1 C7 1.281(2) . ? N1 C10 1.463(2) . ? N1 H1 1.22(4) . ? C1 C6 1.406(2) . ? C1 C2 1.419(2) . ? C2 C3 1.396(2) . ? C2 C7 1.466(2) . ? C3 C4 1.376(2) . ? C3 H2 1.00(3) . ? C4 C5 1.393(3) . ? C5 C6 1.374(3) . ? C5 C8 1.507(2) . ? C6 H3 1.02(3) . ? C7 C9 1.490(3) . ? C8 H4 1.03(3) . ? C8 H5 0.90(3) . ? C8 H6 0.98(3) . ? C9 H7 0.90(5) . ? C9 H8 0.90(4) . ? C9 H9 0.88(5) . ? C10 C11 1.497(3) . ? C10 H10 0.95(2) . ? C10 H11 0.99(2) . ? C11 H12 1.01(3) . ? C11 H13 1.00(3) . ? C11 H14 1.00(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 98.2(17) . . ? C7 N1 C10 124.18(16) . . ? C7 N1 H1 104.9(18) . . ? C10 N1 H1 130.8(18) . . ? O1 C1 C6 119.21(17) . . ? O1 C1 C2 122.45(15) . . ? C6 C1 C2 118.33(17) . . ? C3 C2 C1 118.38(14) . . ? C3 C2 C7 121.61(16) . . ? C1 C2 C7 120.01(15) . . ? C4 C3 C2 120.87(17) . . ? C4 C3 H2 118.9(13) . . ? C2 C3 H2 120.2(13) . . ? C3 C4 C5 122.12(17) . . ? C3 C4 Cl1 118.79(15) . . ? C5 C4 Cl1 119.08(12) . . ? C6 C5 C4 117.07(15) . . ? C6 C5 C8 120.9(2) . . ? C4 C5 C8 122.03(19) . . ? C5 C6 C1 123.17(18) . . ? C5 C6 H3 119.7(15) . . ? C1 C6 H3 117.1(15) . . ? N1 C7 C2 117.07(15) . . ? N1 C7 C9 122.37(15) . . ? C2 C7 C9 120.55(16) . . ? C5 C8 H4 111.5(18) . . ? C5 C8 H5 109(2) . . ? H4 C8 H5 104(3) . . ? C5 C8 H6 109.2(17) . . ? H4 C8 H6 112(3) . . ? H5 C8 H6 112(3) . . ? C7 C9 H7 111(3) . . ? C7 C9 H8 115(3) . . ? H7 C9 H8 102(4) . . ? C7 C9 H9 111(3) . . ? H7 C9 H9 119(4) . . ? H8 C9 H9 97(4) . . ? N1 C10 C11 109.90(18) . . ? N1 C10 H10 109.5(13) . . ? C11 C10 H10 108.7(14) . . ? N1 C10 H11 108.9(12) . . ? C11 C10 H11 111.5(12) . . ? H10 C10 H11 108.3(19) . . ? C10 C11 H12 109.9(17) . . ? C10 C11 H13 113.3(16) . . ? H12 C11 H13 105(2) . . ? C10 C11 H14 111(2) . . ? H12 C11 H14 108(2) . . ? H13 C11 H14 109(3) . . ? 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 178.32(15) . . . . ? C6 C1 C2 C3 -2.6(2) . . . . ? O1 C1 C2 C7 -2.3(2) . . . . ? C6 C1 C2 C7 176.79(15) . . . . ? C1 C2 C3 C4 1.3(2) . . . . ? C7 C2 C3 C4 -178.04(14) . . . . ? C2 C3 C4 C5 0.6(3) . . . . ? C2 C3 C4 Cl1 -179.60(12) . . . . ? C3 C4 C5 C6 -1.1(3) . . . . ? Cl1 C4 C5 C6 179.06(13) . . . . ? C3 C4 C5 C8 179.85(19) . . . . ? Cl1 C4 C5 C8 0.0(3) . . . . ? C4 C5 C6 C1 -0.3(3) . . . . ? C8 C5 C6 C1 178.78(19) . . . . ? O1 C1 C6 C5 -178.76(16) . . . . ? C2 C1 C6 C5 2.1(3) . . . . ? C10 N1 C7 C2 -178.06(14) . . . . ? C10 N1 C7 C9 0.7(3) . . . . ? C3 C2 C7 N1 179.33(14) . . . . ? C1 C2 C7 N1 0.0(2) . . . . ? C3 C2 C7 C9 0.5(2) . . . . ? C1 C2 C7 C9 -178.83(17) . . . . ? C7 N1 C10 C11 175.71(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 N1 H1 O1 1.22(4) 1.33(4) 2.491(2) 155(4) . _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 80.27 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.277 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.047 data_tium21 _database_code_CSD 180650 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H16 Cl N O' _chemical_formula_weight 225.71 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 12.4205(10) _cell_length_b 7.1853(6) _cell_length_c 25.571(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.056(6) _cell_angle_gamma 90.00 _cell_volume 2281.7(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _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 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.308 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _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 'Kuma KM4CCD automatic diffractometer' _diffrn_measurement_method 'profile data from omega/2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12659 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4457 _reflns_number_gt 3190 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kuma KM4CCD software 1998' _computing_cell_refinement 'Kuma KM4CCD software 1998' _computing_data_reduction 'Kuma KM4CCD software 1998' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.2152P] 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 4457 _refine_ls_number_parameters 399 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0761 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1272 _refine_ls_wR_factor_gt 0.1143 _refine_ls_goodness_of_fit_ref 1.147 _refine_ls_restrained_S_all 1.147 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl11 Cl 0.67345(4) 0.72097(8) 0.22278(2) 0.02609(18) Uani 1 d . . . O11 O 0.23617(13) 0.7093(2) 0.13196(6) 0.0246(4) Uani 1 d . . . N11 N 0.16326(15) 0.7320(2) 0.22195(7) 0.0160(4) Uani 1 d . . . C11 C 0.33496(18) 0.7116(3) 0.15442(8) 0.0177(5) Uani 1 d . . . C12 C 0.35022(18) 0.7218(3) 0.20929(8) 0.0148(5) Uani 1 d . . . C13 C 0.45717(18) 0.7241(3) 0.22968(9) 0.0158(5) Uani 1 d . . . C14 C 0.54310(18) 0.7165(3) 0.19615(9) 0.0169(5) Uani 1 d . . . C15 C 0.52895(18) 0.7058(3) 0.14144(8) 0.0186(5) Uani 1 d . . . C16 C 0.42451(19) 0.7025(3) 0.12189(9) 0.0215(5) Uani 1 d . . . C17 C 0.25710(19) 0.7290(3) 0.24417(8) 0.0155(5) Uani 1 d . . . C18 C 0.6228(2) 0.6990(3) 0.10523(10) 0.0241(5) Uani 1 d . . . C19 C 0.2750(2) 0.7307(3) 0.30250(9) 0.0216(5) Uani 1 d . . . C110 C 0.06328(19) 0.7451(3) 0.25145(9) 0.0190(5) Uani 1 d . . . C111 C -0.03085(19) 0.7832(3) 0.21373(9) 0.0206(5) Uani 1 d . . . C112 C -0.0616(2) 0.6163(3) 0.18034(10) 0.0246(5) Uani 1 d . . . Cl21 Cl 0.57529(5) 0.24937(8) 0.02844(2) 0.02535(18) Uani 1 d . . . O21 O 1.01189(12) 0.1837(2) 0.11838(6) 0.0224(4) Uani 1 d . . . N21 N 1.08551(16) 0.2412(2) 0.02950(7) 0.0180(4) Uani 1 d . . . C21 C 0.91312(18) 0.1942(3) 0.09618(8) 0.0171(5) Uani 1 d . . . C22 C 0.89756(18) 0.2200(3) 0.04120(8) 0.0153(5) Uani 1 d . . . C23 C 0.79203(19) 0.2352(3) 0.02177(9) 0.0159(5) Uani 1 d . . . C24 C 0.70597(18) 0.2248(3) 0.05478(9) 0.0166(5) Uani 1 d . . . C25 C 0.71909(17) 0.1965(3) 0.10872(8) 0.0174(5) Uani 1 d . . . C26 C 0.82384(18) 0.1802(3) 0.12805(9) 0.0193(5) Uani 1 d . . . C27 C 0.99148(19) 0.2390(3) 0.00655(9) 0.0156(5) Uani 1 d . . . C28 C 0.6250(2) 0.1874(3) 0.14491(10) 0.0237(5) Uani 1 d . . . C29 C 0.9746(2) 0.2585(4) -0.05135(10) 0.0212(5) Uani 1 d . . . C210 C 1.18428(19) 0.2733(3) 0.00017(9) 0.0187(5) Uani 1 d . . . C211 C 1.27700(19) 0.3116(3) 0.03878(10) 0.0244(5) Uani 1 d . . . C212 C 1.3131(2) 0.1385(4) 0.06787(10) 0.0260(5) Uani 1 d . . . H1 H 0.188(3) 0.730(4) 0.1649(16) 0.078(12) Uiso 1 d . . . H2 H 0.472(2) 0.734(3) 0.2670(12) 0.039(8) Uiso 1 d . . . H3 H 0.4131(17) 0.700(3) 0.0849(9) 0.013(5) Uiso 1 d . . . H4 H 0.678(2) 0.808(4) 0.1124(11) 0.047(8) Uiso 1 d . . . H5 H 0.676(2) 0.593(4) 0.1149(10) 0.044(7) Uiso 1 d . . . H6 H 0.597(2) 0.700(3) 0.0664(11) 0.036(7) Uiso 1 d . . . H7 H 0.323(3) 0.640(4) 0.3168(12) 0.066(10) Uiso 1 d . . . H8 H 0.314(3) 0.831(5) 0.3148(13) 0.067(10) Uiso 1 d . . . H9 H 0.207(6) 0.718(7) 0.317(3) 0.18(3) Uiso 1 d . . . H10 H 0.0721(16) 0.841(3) 0.2770(8) 0.012(5) Uiso 1 d . . . H11 H 0.0551(17) 0.631(3) 0.2709(8) 0.018(6) Uiso 1 d . . . H12 H -0.0935(19) 0.823(3) 0.2347(8) 0.017(5) Uiso 1 d . . . H13 H -0.0131(18) 0.893(3) 0.1917(8) 0.023(6) Uiso 1 d . . . H14 H -0.0914(18) 0.516(3) 0.2002(9) 0.030(6) Uiso 1 d . . . H15 H 0.000(2) 0.571(3) 0.1619(9) 0.035(7) Uiso 1 d . . . H16 H -0.121(2) 0.647(3) 0.1519(10) 0.038(7) Uiso 1 d . . . H17 H 1.060(2) 0.211(3) 0.0869(11) 0.039(8) Uiso 1 d . . . H18 H 0.780(2) 0.254(3) -0.0133(10) 0.021(7) Uiso 1 d . . . H19 H 0.838(2) 0.160(3) 0.1656(10) 0.034(7) Uiso 1 d . . . H20 H 0.570(2) 0.090(4) 0.1314(10) 0.053(8) Uiso 1 d . . . H21 H 0.590(2) 0.309(3) 0.1478(9) 0.027(6) Uiso 1 d . . . H22 H 0.645(2) 0.149(3) 0.1767(10) 0.033(7) Uiso 1 d . . . H23 H 0.922(3) 0.190(4) -0.0643(12) 0.059(10) Uiso 1 d . . . H24 H 0.960(3) 0.376(5) -0.0580(12) 0.069(10) Uiso 1 d . . . H25 H 1.033(3) 0.210(3) -0.0692(11) 0.039(8) Uiso 1 d . . . H26 H 1.1750(18) 0.379(3) -0.0223(9) 0.026(6) Uiso 1 d . . . H27 H 1.2019(18) 0.163(3) -0.0195(9) 0.020(6) Uiso 1 d . . . H28 H 1.3374(18) 0.366(3) 0.0190(8) 0.022(6) Uiso 1 d . . . H29 H 1.2577(17) 0.403(3) 0.0661(8) 0.021(6) Uiso 1 d . . . H30 H 1.3440(18) 0.052(3) 0.0425(9) 0.029(6) Uiso 1 d . . . H31 H 1.252(2) 0.084(3) 0.0856(9) 0.027(6) Uiso 1 d . . . H32 H 1.368(2) 0.167(3) 0.0930(10) 0.031(7) Uiso 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 Cl11 0.0116(3) 0.0442(4) 0.0224(3) 0.0007(2) -0.0003(2) -0.0003(2) O11 0.0158(9) 0.0401(10) 0.0179(9) 0.0004(7) -0.0026(7) -0.0015(7) N11 0.0114(10) 0.0201(9) 0.0164(10) 0.0008(7) 0.0008(8) 0.0011(7) C11 0.0154(12) 0.0206(11) 0.0170(11) 0.0012(8) -0.0020(9) -0.0009(8) C12 0.0133(12) 0.0159(10) 0.0153(11) 0.0007(8) 0.0012(9) -0.0010(8) C13 0.0152(12) 0.0176(10) 0.0147(12) 0.0011(8) -0.0004(9) -0.0012(8) C14 0.0127(12) 0.0175(10) 0.0204(12) 0.0001(8) -0.0012(9) 0.0002(8) C15 0.0197(12) 0.0164(10) 0.0199(12) -0.0005(8) 0.0037(9) -0.0015(9) C16 0.0235(13) 0.0249(11) 0.0161(12) -0.0025(9) 0.0006(10) -0.0024(10) C17 0.0164(12) 0.0142(10) 0.0160(12) 0.0001(8) 0.0008(10) 0.0015(8) C18 0.0183(13) 0.0317(13) 0.0227(13) -0.0024(10) 0.0075(10) -0.0013(10) C19 0.0165(13) 0.0339(13) 0.0143(12) 0.0008(9) -0.0002(10) 0.0032(10) C110 0.0161(13) 0.0190(11) 0.0221(13) -0.0005(9) 0.0047(10) -0.0008(8) C111 0.0144(12) 0.0264(12) 0.0210(12) 0.0020(10) 0.0003(10) 0.0026(9) C112 0.0183(12) 0.0313(13) 0.0240(13) 0.0000(10) -0.0008(10) -0.0019(10) Cl21 0.0118(3) 0.0427(4) 0.0215(3) 0.0004(2) -0.0002(2) 0.0007(2) O21 0.0151(8) 0.0358(9) 0.0162(8) 0.0016(7) -0.0037(7) 0.0011(7) N21 0.0164(11) 0.0177(9) 0.0200(11) 0.0002(7) 0.0020(9) -0.0006(7) C21 0.0181(12) 0.0176(10) 0.0154(11) -0.0013(8) -0.0024(9) 0.0008(9) C22 0.0159(12) 0.0144(10) 0.0157(11) -0.0010(8) 0.0022(9) -0.0006(8) C23 0.0171(13) 0.0155(10) 0.0152(12) -0.0007(8) 0.0005(10) -0.0007(8) C24 0.0126(12) 0.0179(10) 0.0193(12) -0.0021(8) 0.0002(9) 0.0004(8) C25 0.0169(12) 0.0171(10) 0.0182(11) -0.0012(8) 0.0025(9) -0.0010(9) C26 0.0210(12) 0.0231(11) 0.0139(11) -0.0003(9) 0.0012(9) 0.0012(9) C27 0.0138(12) 0.0149(10) 0.0182(12) -0.0013(8) 0.0002(10) 0.0019(8) C28 0.0222(13) 0.0276(13) 0.0214(13) 0.0031(10) 0.0064(10) 0.0010(11) C29 0.0173(14) 0.0286(13) 0.0178(13) -0.0029(9) 0.0022(11) 0.0024(10) C210 0.0149(12) 0.0230(12) 0.0181(12) 0.0019(9) 0.0003(10) 0.0001(9) C211 0.0166(12) 0.0290(12) 0.0277(13) -0.0045(11) 0.0039(10) -0.0035(10) C212 0.0179(12) 0.0363(14) 0.0239(13) -0.0024(11) 0.0002(11) -0.0010(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl11 C14 1.745(2) . ? O11 C11 1.345(3) . ? O11 H1 1.05(4) . ? N11 C17 1.287(3) . ? N11 C110 1.468(3) . ? N11 H1 1.50(4) . ? C11 C16 1.403(3) . ? C11 C12 1.414(3) . ? C12 C13 1.418(3) . ? C12 C17 1.474(3) . ? C13 C14 1.382(3) . ? C13 H2 0.97(3) . ? C14 C15 1.409(3) . ? C15 C16 1.382(3) . ? C15 C18 1.503(3) . ? C16 H3 0.95(2) . ? C17 C19 1.504(3) . ? C18 H4 1.05(3) . ? C18 H5 1.03(3) . ? C18 H6 1.04(3) . ? C19 H7 0.95(3) . ? C19 H8 0.92(3) . ? C19 H9 0.93(7) . ? C110 C111 1.527(3) . ? C110 H10 0.95(2) . ? C110 H11 0.97(2) . ? C111 C112 1.517(3) . ? C111 H12 1.00(2) . ? C111 H13 1.00(2) . ? C112 H14 0.96(2) . ? C112 H15 0.97(3) . ? C112 H16 1.05(3) . ? Cl21 C24 1.755(2) . ? O21 C21 1.344(2) . ? O21 H17 1.03(3) . ? N21 C27 1.297(3) . ? N21 C210 1.468(3) . ? N21 H17 1.52(3) . ? C21 C26 1.392(3) . ? C21 C22 1.428(3) . ? C22 C23 1.397(3) . ? C22 C27 1.484(3) . ? C23 C24 1.376(3) . ? C23 H18 0.92(3) . ? C24 C25 1.401(3) . ? C25 C26 1.388(3) . ? C25 C28 1.505(3) . ? C26 H19 0.99(3) . ? C27 C29 1.498(3) . ? C28 H20 1.03(3) . ? C28 H21 0.98(2) . ? C28 H22 0.89(3) . ? C29 H23 0.88(3) . ? C29 H24 0.88(3) . ? C29 H25 0.93(3) . ? C210 C211 1.528(3) . ? C210 H26 0.96(2) . ? C210 H27 0.97(2) . ? C211 C212 1.513(4) . ? C211 H28 0.99(2) . ? C211 H29 0.99(2) . ? C212 H30 0.98(2) . ? C212 H31 0.97(2) . ? C212 H32 0.95(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O11 H1 101(2) . . ? C17 N11 C110 122.82(19) . . ? C17 N11 H1 103.3(15) . . ? C110 N11 H1 133.8(15) . . ? O11 C11 C16 118.3(2) . . ? O11 C11 C12 121.9(2) . . ? C16 C11 C12 119.8(2) . . ? C11 C12 C13 118.2(2) . . ? C11 C12 C17 120.6(2) . . ? C13 C12 C17 121.1(2) . . ? C14 C13 C12 120.0(2) . . ? C14 C13 H2 118.3(18) . . ? C12 C13 H2 121.6(18) . . ? C13 C14 C15 122.3(2) . . ? C13 C14 Cl11 118.59(17) . . ? C15 C14 Cl11 119.11(17) . . ? C16 C15 C14 117.3(2) . . ? C16 C15 C18 120.7(2) . . ? C14 C15 C18 122.0(2) . . ? C15 C16 C11 122.3(2) . . ? C15 C16 H3 118.7(13) . . ? C11 C16 H3 119.0(13) . . ? N11 C17 C12 116.59(19) . . ? N11 C17 C19 123.6(2) . . ? C12 C17 C19 119.8(2) . . ? C15 C18 H4 112.2(15) . . ? C15 C18 H5 112.1(14) . . ? H4 C18 H5 95(2) . . ? C15 C18 H6 111.0(15) . . ? H4 C18 H6 111(2) . . ? H5 C18 H6 115(2) . . ? C17 C19 H7 117.2(19) . . ? C17 C19 H8 114(2) . . ? H7 C19 H8 95(3) . . ? C17 C19 H9 106(4) . . ? H7 C19 H9 110(4) . . ? H8 C19 H9 114(4) . . ? N11 C110 C111 109.40(19) . . ? N11 C110 H10 108.1(12) . . ? C111 C110 H10 112.4(12) . . ? N11 C110 H11 108.0(13) . . ? C111 C110 H11 113.0(13) . . ? H10 C110 H11 105.7(18) . . ? C112 C111 C110 113.31(19) . . ? C112 C111 H12 109.9(12) . . ? C110 C111 H12 108.0(12) . . ? C112 C111 H13 111.4(12) . . ? C110 C111 H13 108.9(13) . . ? H12 C111 H13 105.0(18) . . ? C111 C112 H14 113.1(14) . . ? C111 C112 H15 110.2(14) . . ? H14 C112 H15 109(2) . . ? C111 C112 H16 112.9(14) . . ? H14 C112 H16 104.5(19) . . ? H15 C112 H16 107.0(19) . . ? C21 O21 H17 101.5(15) . . ? C27 N21 C210 121.64(19) . . ? C27 N21 H17 103.6(11) . . ? C210 N21 H17 134.7(11) . . ? O21 C21 C26 118.65(19) . . ? O21 C21 C22 121.94(19) . . ? C26 C21 C22 119.4(2) . . ? C23 C22 C21 118.0(2) . . ? C23 C22 C27 121.5(2) . . ? C21 C22 C27 120.4(2) . . ? C24 C23 C22 120.8(2) . . ? C24 C23 H18 119.3(16) . . ? C22 C23 H18 119.9(16) . . ? C23 C24 C25 122.3(2) . . ? C23 C24 Cl21 118.85(18) . . ? C25 C24 Cl21 118.85(17) . . ? C26 C25 C24 117.0(2) . . ? C26 C25 C28 120.7(2) . . ? C24 C25 C28 122.3(2) . . ? C25 C26 C21 122.5(2) . . ? C25 C26 H19 120.7(15) . . ? C21 C26 H19 116.8(14) . . ? N21 C27 C22 116.2(2) . . ? N21 C27 C29 123.7(2) . . ? C22 C27 C29 120.1(2) . . ? C25 C28 H20 109.9(15) . . ? C25 C28 H21 111.0(14) . . ? H20 C28 H21 110(2) . . ? C25 C28 H22 111.7(16) . . ? H20 C28 H22 106(2) . . ? H21 C28 H22 109(2) . . ? C27 C29 H23 114(2) . . ? C27 C29 H24 108(2) . . ? H23 C29 H24 109(3) . . ? C27 C29 H25 110.7(17) . . ? H23 C29 H25 100(3) . . ? H24 C29 H25 115(3) . . ? N21 C210 C211 108.98(19) . . ? N21 C210 H26 109.8(13) . . ? C211 C210 H26 109.1(13) . . ? N21 C210 H27 109.7(13) . . ? C211 C210 H27 108.0(13) . . ? H26 C210 H27 111(2) . . ? C212 C211 C210 112.5(2) . . ? C212 C211 H28 110.9(13) . . ? C210 C211 H28 108.0(12) . . ? C212 C211 H29 105.9(12) . . ? C210 C211 H29 112.6(13) . . ? H28 C211 H29 106.8(18) . . ? C211 C212 H30 108.2(13) . . ? C211 C212 H31 109.6(14) . . ? H30 C212 H31 111.7(19) . . ? C211 C212 H32 111.1(15) . . ? H30 C212 H32 107.2(19) . . ? H31 C212 H32 109(2) . . ? 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 O11 C11 C12 C13 -179.79(18) . . . . ? C16 C11 C12 C13 0.5(3) . . . . ? O11 C11 C12 C17 0.5(3) . . . . ? C16 C11 C12 C17 -179.24(18) . . . . ? C11 C12 C13 C14 0.0(3) . . . . ? C17 C12 C13 C14 179.77(17) . . . . ? C12 C13 C14 C15 -0.2(3) . . . . ? C12 C13 C14 Cl11 179.63(14) . . . . ? C13 C14 C15 C16 -0.2(3) . . . . ? Cl11 C14 C15 C16 179.99(15) . . . . ? C13 C14 C15 C18 179.56(19) . . . . ? Cl11 C14 C15 C18 -0.3(3) . . . . ? C14 C15 C16 C11 0.7(3) . . . . ? C18 C15 C16 C11 -179.0(2) . . . . ? O11 C11 C16 C15 179.37(19) . . . . ? C12 C11 C16 C15 -0.9(3) . . . . ? C110 N11 C17 C12 -178.02(17) . . . . ? C110 N11 C17 C19 2.6(3) . . . . ? C11 C12 C17 N11 -2.3(3) . . . . ? C13 C12 C17 N11 177.96(18) . . . . ? C11 C12 C17 C19 177.11(19) . . . . ? C13 C12 C17 C19 -2.6(3) . . . . ? C17 N11 C110 C111 169.09(18) . . . . ? N11 C110 C111 C112 72.2(2) . . . . ? O21 C21 C22 C23 -178.02(18) . . . . ? C26 C21 C22 C23 1.6(3) . . . . ? O21 C21 C22 C27 -0.9(3) . . . . ? C26 C21 C22 C27 178.81(18) . . . . ? C21 C22 C23 C24 -0.2(3) . . . . ? C27 C22 C23 C24 -177.33(18) . . . . ? C22 C23 C24 C25 -0.8(3) . . . . ? C22 C23 C24 Cl21 178.74(15) . . . . ? C23 C24 C25 C26 0.4(3) . . . . ? Cl21 C24 C25 C26 -179.19(15) . . . . ? C23 C24 C25 C28 179.25(19) . . . . ? Cl21 C24 C25 C28 -0.3(3) . . . . ? C24 C25 C26 C21 1.1(3) . . . . ? C28 C25 C26 C21 -177.7(2) . . . . ? O21 C21 C26 C25 177.50(19) . . . . ? C22 C21 C26 C25 -2.2(3) . . . . ? C210 N21 C27 C22 -175.34(17) . . . . ? C210 N21 C27 C29 3.3(3) . . . . ? C23 C22 C27 N21 173.30(18) . . . . ? C21 C22 C27 N21 -3.8(3) . . . . ? C23 C22 C27 C29 -5.4(3) . . . . ? C21 C22 C27 C29 177.55(19) . . . . ? C27 N21 C210 C211 167.26(18) . . . . ? N21 C210 C211 C212 72.6(2) . . . . ? 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 O11 H1 N11 1.05(4) 1.50(4) 2.494(2) 156(3) . O21 H17 N21 1.03(3) 1.52(3) 2.500(2) 156(3) . _diffrn_measured_fraction_theta_max 0.917 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.917 _refine_diff_density_max 0.247 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.057