# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 # CCDC Number: 188/287 data_global _journal_coden_Cambridge 207 data_ak9705 _database_code_CSD 188/287 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H26 I N O' _chemical_formula_weight 351.26 _chemical_melting_point ? _chemical_compound_source ? 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' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 12.130(11) _cell_length_b 8.810(7) _cell_length_c 14.747(12) _cell_angle_alpha 90.00 _cell_angle_beta 101.76(7) _cell_angle_gamma 90.00 _cell_volume 1542.9(22) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 30 _cell_measurement_theta_max 35 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method ? _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 2.064 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku R-Axis IIc' _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10426 _diffrn_reflns_av_R_equivalents 0.0740 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.33 _reflns_number_total 2615 _reflns_number_observed 2385 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 9 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0243P)^2^+7.9419P] 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 refU _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2606 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0982 _refine_ls_R_factor_obs 0.0872 _refine_ls_wR_factor_all 0.1572 _refine_ls_wR_factor_obs 0.1473 _refine_ls_goodness_of_fit_all 1.293 _refine_ls_goodness_of_fit_obs 1.312 _refine_ls_restrained_S_all 1.340 _refine_ls_restrained_S_obs 1.312 _refine_ls_shift/esd_max 0.012 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group I1 I -0.31685(6) 0.10678(8) 0.91923(5) 0.0714(3) Uani 1 d . . C6 C -0.1065(5) 0.1293(7) 0.6997(5) 0.0295(15) Uani 1 d . . C14 C 0.1164(7) 0.2476(9) 0.7785(6) 0.046(2) Uani 1 d . . H14A H 0.1912(7) 0.2361(9) 0.8199(6) 0.055 Uiso 1 calc R . H14B H 0.1142(7) 0.3471(9) 0.7470(6) 0.055 Uiso 1 calc R . C1 C -0.0884(7) 0.2550(9) 0.7707(6) 0.048(2) Uani 1 d . . H1A H -0.0935(7) 0.3544(9) 0.7387(6) 0.057 Uiso 1 calc R . H1B H -0.1482(7) 0.2510(9) 0.8073(6) 0.057 Uiso 1 calc R . C2 C 0.0251(7) 0.2404(8) 0.8346(5) 0.045(2) Uani 1 d . . C3 C 0.0307(7) 0.0866(8) 0.8831(5) 0.046(2) Uani 1 d . . H3A H 0.1050(7) 0.0754(8) 0.9253(5) 0.055 Uiso 1 calc R . H3B H -0.0280(7) 0.0819(8) 0.9208(5) 0.055 Uiso 1 calc R . C4 C 0.0136(6) -0.0419(8) 0.8141(6) 0.042(2) Uani 1 d . . C5 C 0.1025(6) -0.0329(8) 0.7562(5) 0.041(2) Uani 1 d . . H5A H 0.0913(6) -0.1165(8) 0.7104(5) 0.050 Uiso 1 calc R . H5B H 0.1778(6) -0.0455(8) 0.7967(5) 0.050 Uiso 1 calc R . N1 N 0.0977(6) 0.1187(8) 0.7058(5) 0.058(2) Uani 1 d . . C7 C -0.0148(7) 0.1365(8) 0.6460(6) 0.044(2) Uani 1 d . . C8 C -0.0998(6) -0.0228(9) 0.7502(6) 0.046(2) Uani 1 d . . H8A H -0.1599(6) -0.0282(9) 0.7866(6) 0.055 Uiso 1 calc R . H8B H -0.1120(6) -0.1064(9) 0.7044(6) 0.055 Uiso 1 calc R . C9 C 0.0396(10) 0.3699(10) 0.9040(6) 0.068(3) Uani 1 d . . H9A H 0.1132(10) 0.3614(10) 0.9459(6) 0.082 Uiso 1 calc R . H9B H -0.0200(10) 0.3649(10) 0.9399(6) 0.082 Uiso 1 calc R . H9C H 0.0349(10) 0.4670(10) 0.8710(6) 0.082 Uiso 1 calc R . C10 C 0.0184(8) -0.1949(9) 0.8610(6) 0.057(2) Uani 1 d . . H10A H -0.0395(8) -0.2000(9) 0.8985(6) 0.068 Uiso 1 calc R . H10B H 0.0928(8) -0.2090(9) 0.9010(6) 0.068 Uiso 1 calc R . H10C H 0.0052(8) -0.2751(9) 0.8139(6) 0.068 Uiso 1 calc R . C11 C 0.1912(8) 0.1268(11) 0.6529(7) 0.067(3) Uani 1 d . . H11A H 0.2638(8) 0.1143(11) 0.6959(7) 0.080 Uiso 1 calc R . H11B H 0.1893(8) 0.2256(11) 0.6221(7) 0.080 Uiso 1 calc R . H11C H 0.1816(8) 0.0458(11) 0.6065(7) 0.080 Uiso 1 calc R . C12 C -0.0348(9) 0.1649(11) 0.5576(6) 0.068(3) Uani 1 d . . H12A H 0.0260(9) 0.1758(11) 0.5264(6) 0.082 Uiso 1 calc R . H12B H -0.1102(9) 0.1746(11) 0.5242(6) 0.082 Uiso 1 calc R . C13 C -0.2217(7) 0.1439(11) 0.6422(7) 0.070(3) Uani 1 d . . H13A H -0.2771(7) 0.1381(11) 0.6820(7) 0.084 Uiso 1 calc R . H13B H -0.2351(7) 0.0615(11) 0.5966(7) 0.084 Uiso 1 calc R . H13C H -0.2288(7) 0.2417(11) 0.6099(7) 0.084 Uiso 1 calc R . O1 O 0.3807(10) 0.0799(13) 0.8770(7) 0.102(3) Uani 1 d . . H1O H 0.3601(148) 0.0436(206) 0.9327(132) 0.186(84) Uiso 1 d . . H2O H 0.4460(96) 0.0867(127) 0.8858(75) 0.072(38) 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 I1 0.0668(4) 0.0753(5) 0.0785(5) -0.0055(4) 0.0303(3) 0.0015(4) C6 0.028(3) 0.024(4) 0.035(4) 0.004(3) 0.003(3) 0.003(3) C14 0.048(5) 0.036(4) 0.053(5) 0.003(4) 0.004(4) -0.008(4) C1 0.054(5) 0.036(4) 0.057(5) 0.006(4) 0.019(4) 0.008(4) C2 0.060(5) 0.031(4) 0.042(5) -0.001(3) 0.011(4) 0.001(4) C3 0.054(5) 0.039(5) 0.044(5) 0.006(4) 0.008(4) 0.001(4) C4 0.038(4) 0.036(4) 0.054(5) 0.008(4) 0.009(4) -0.002(3) C5 0.041(4) 0.032(4) 0.050(5) 0.014(3) 0.009(4) 0.008(3) N1 0.049(4) 0.059(5) 0.068(5) 0.012(4) 0.020(3) 0.000(4) C7 0.050(5) 0.037(4) 0.047(5) 0.005(3) 0.014(4) 0.003(3) C8 0.039(4) 0.041(4) 0.057(5) 0.003(4) 0.009(4) -0.008(4) C9 0.105(8) 0.044(5) 0.054(6) -0.006(4) 0.012(5) 0.001(5) C10 0.065(6) 0.032(4) 0.072(6) 0.015(4) 0.012(5) -0.001(4) C11 0.058(6) 0.067(6) 0.085(7) 0.007(5) 0.038(5) -0.005(5) C12 0.080(7) 0.072(6) 0.052(6) 0.013(5) 0.011(5) 0.000(5) C13 0.042(5) 0.076(7) 0.085(7) 0.014(5) -0.004(5) 0.008(5) O1 0.080(7) 0.131(8) 0.087(7) 0.002(6) -0.005(5) -0.010(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 C6 C13 1.485(10) . ? C6 C7 1.492(10) . ? C6 C1 1.509(10) . ? C6 C8 1.527(10) . ? C14 C2 1.513(11) . ? C14 N1 1.546(11) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C1 C2 1.507(11) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 C9 1.519(11) . ? C2 C3 1.527(10) . ? C3 C4 1.508(11) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 C5 1.508(10) . ? C4 C8 1.509(11) . ? C4 C10 1.511(10) . ? C5 N1 1.524(10) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? N1 C7 1.474(11) . ? N1 C11 1.503(10) . ? C7 C12 1.301(11) . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 H9C 0.98 . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? C11 H11A 0.98 . ? C11 H11B 0.98 . ? C11 H11C 0.98 . ? C12 H12A 0.95 . ? C12 H12B 0.95 . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? O1 H1O 0.96(18) . ? O1 H2O 0.78(11) . ? 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 C13 C6 C7 114.2(7) . . ? C13 C6 C1 108.6(6) . . ? C7 C6 C1 108.5(6) . . ? C13 C6 C8 107.8(6) . . ? C7 C6 C8 109.0(6) . . ? C1 C6 C8 108.7(6) . . ? C2 C14 N1 109.2(6) . . ? C2 C14 H14A 109.8(5) . . ? N1 C14 H14A 109.8(4) . . ? C2 C14 H14B 109.8(4) . . ? N1 C14 H14B 109.8(4) . . ? H14A C14 H14B 108.3 . . ? C2 C1 C6 110.9(6) . . ? C2 C1 H1A 109.5(4) . . ? C6 C1 H1A 109.5(4) . . ? C2 C1 H1B 109.5(4) . . ? C6 C1 H1B 109.5(4) . . ? H1A C1 H1B 108.1 . . ? C1 C2 C14 109.4(7) . . ? C1 C2 C9 108.9(7) . . ? C14 C2 C9 109.9(7) . . ? C1 C2 C3 108.5(7) . . ? C14 C2 C3 109.0(6) . . ? C9 C2 C3 111.3(7) . . ? C4 C3 C2 111.3(6) . . ? C4 C3 H3A 109.4(4) . . ? C2 C3 H3A 109.4(4) . . ? C4 C3 H3B 109.4(4) . . ? C2 C3 H3B 109.4(4) . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 109.0(6) . . ? C5 C4 C8 107.9(7) . . ? C3 C4 C8 108.7(6) . . ? C5 C4 C10 109.9(6) . . ? C3 C4 C10 112.0(7) . . ? C8 C4 C10 109.3(6) . . ? C4 C5 N1 111.2(6) . . ? C4 C5 H5A 109.4(4) . . ? N1 C5 H5A 109.4(4) . . ? C4 C5 H5B 109.4(4) . . ? N1 C5 H5B 109.4(4) . . ? H5A C5 H5B 108.0 . . ? C7 N1 C11 113.0(7) . . ? C7 N1 C5 108.9(6) . . ? C11 N1 C5 109.7(6) . . ? C7 N1 C14 108.9(6) . . ? C11 N1 C14 107.7(7) . . ? C5 N1 C14 108.6(6) . . ? C12 C7 N1 125.5(8) . . ? C12 C7 C6 122.2(8) . . ? N1 C7 C6 112.2(7) . . ? C4 C8 C6 110.7(6) . . ? C4 C8 H8A 109.5(4) . . ? C6 C8 H8A 109.5(4) . . ? C4 C8 H8B 109.5(4) . . ? C6 C8 H8B 109.5(4) . . ? H8A C8 H8B 108.1 . . ? C2 C9 H9A 109.5(5) . . ? C2 C9 H9B 109.5(5) . . ? H9A C9 H9B 109.5 . . ? C2 C9 H9C 109.5(5) . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 C10 H10A 109.5(5) . . ? C4 C10 H10B 109.5(4) . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5(5) . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 H11A 109.5(5) . . ? N1 C11 H11B 109.5(5) . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5(5) . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C7 C12 H12A 120.0(6) . . ? C7 C12 H12B 120.0(6) . . ? H12A C12 H12B 120.0 . . ? C6 C13 H13A 109.5(5) . . ? C6 C13 H13B 109.5(5) . . ? H13A C13 H13B 109.5 . . ? C6 C13 H13C 109.5(5) . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? H1O O1 H2O 108.5(100) . . ? 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 C13 C6 C1 C2 176.8(7) . . . . ? C7 C6 C1 C2 -58.5(8) . . . . ? C8 C6 C1 C2 59.8(8) . . . . ? C6 C1 C2 C14 59.5(8) . . . . ? C6 C1 C2 C9 179.5(6) . . . . ? C6 C1 C2 C3 -59.3(8) . . . . ? N1 C14 C2 C1 -58.4(8) . . . . ? N1 C14 C2 C9 -177.9(6) . . . . ? N1 C14 C2 C3 60.0(8) . . . . ? C1 C2 C3 C4 58.9(8) . . . . ? C14 C2 C3 C4 -60.0(9) . . . . ? C9 C2 C3 C4 178.7(7) . . . . ? C2 C3 C4 C5 58.4(8) . . . . ? C2 C3 C4 C8 -58.9(8) . . . . ? C2 C3 C4 C10 -179.8(7) . . . . ? C3 C4 C5 N1 -58.6(9) . . . . ? C8 C4 C5 N1 59.3(8) . . . . ? C10 C4 C5 N1 178.4(7) . . . . ? C4 C5 N1 C7 -58.9(9) . . . . ? C4 C5 N1 C11 177.0(7) . . . . ? C4 C5 N1 C14 59.5(8) . . . . ? C2 C14 N1 C7 58.5(8) . . . . ? C2 C14 N1 C11 -178.7(7) . . . . ? C2 C14 N1 C5 -60.0(8) . . . . ? C11 N1 C7 C12 -3.7(12) . . . . ? C5 N1 C7 C12 -125.8(9) . . . . ? C14 N1 C7 C12 116.0(9) . . . . ? C11 N1 C7 C6 -179.6(6) . . . . ? C5 N1 C7 C6 58.3(8) . . . . ? C14 N1 C7 C6 -60.0(8) . . . . ? C13 C6 C7 C12 5.0(11) . . . . ? C1 C6 C7 C12 -116.3(9) . . . . ? C8 C6 C7 C12 125.5(8) . . . . ? C13 C6 C7 N1 -179.0(7) . . . . ? C1 C6 C7 N1 59.7(8) . . . . ? C8 C6 C7 N1 -58.4(8) . . . . ? C5 C4 C8 C6 -59.1(8) . . . . ? C3 C4 C8 C6 59.0(8) . . . . ? C10 C4 C8 C6 -178.5(6) . . . . ? C13 C6 C8 C4 -177.0(7) . . . . ? C7 C6 C8 C4 58.6(8) . . . . ? C1 C6 C8 C4 -59.5(8) . . . . ? _refine_diff_density_max 0.691 _refine_diff_density_min -0.677 _refine_diff_density_rms 0.094 data_ak9801 _database_code_CSD 188/287 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H24 Cl N O2' _chemical_formula_weight 261.78 _chemical_melting_point ? _chemical_compound_source ? 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.527(8) _cell_length_b 14.498(4) _cell_length_c 7.796(2) _cell_angle_alpha 90.05(2) _cell_angle_beta 90.45(4) _cell_angle_gamma 86.77(4) _cell_volume 1413.6(10) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method ? _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.262 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device AFC5R _diffrn_measurement_method omega/2theta scans _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5615 _diffrn_reflns_av_R_equivalents 0.0879 _diffrn_reflns_av_sigmaI/netI 0.1965 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4987 _reflns_number_observed 2353 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 39 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0405P)^2^+4.0558P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4948 _refine_ls_number_parameters 328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2124 _refine_ls_R_factor_obs 0.0759 _refine_ls_wR_factor_all 0.2531 _refine_ls_wR_factor_obs 0.1663 _refine_ls_goodness_of_fit_all 1.073 _refine_ls_goodness_of_fit_obs 1.209 _refine_ls_restrained_S_all 1.234 _refine_ls_restrained_S_obs 1.209 _refine_ls_shift/esd_max 0.040 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cl1_1 Cl 0.46929(14) 0.37714(12) 0.7075(2) 0.0355(5) Uani 1 d . . O1_1 O 0.3063(4) 0.3039(3) 0.4548(6) 0.0331(11) Uani 1 d . . H1_1 H 0.3642(62) 0.3154(51) 0.5411(93) 0.050(11) Uiso 1 d . . O2_1 O 0.3058(4) 0.4636(3) 0.4574(6) 0.0340(12) Uani 1 d . . H2_1 H 0.3689(63) 0.4547(51) 0.5176(93) 0.050(11) Uiso 1 d . . N1_1 N 0.3546(4) 0.3834(4) 0.1974(7) 0.0282(13) Uani 1 d . . C1_1 C 0.4709(5) 0.3755(4) 0.2405(9) 0.032(2) Uani 1 d . . H1B_1 H 0.5123(6) 0.3688(29) 0.1347(9) 0.049 Uiso 1 calc R . H1C_1 H 0.4861(8) 0.3212(16) 0.3135(44) 0.049 Uiso 1 calc R . H1D_1 H 0.4906(9) 0.4311(13) 0.3017(47) 0.049 Uiso 1 calc R . C2_1 C 0.2830(6) 0.3853(4) 0.3688(8) 0.030(2) Uani 1 d . . C3_1 C 0.1640(5) 0.3929(5) 0.3105(8) 0.031(2) Uani 1 d . . C4_1 C 0.0941(6) 0.3932(6) 0.4701(9) 0.045(2) Uani 1 d . . H4A_1 H 0.0188(7) 0.4034(35) 0.4364(11) 0.067 Uiso 1 calc R . H4B_1 H 0.1141(27) 0.4429(22) 0.5474(30) 0.067 Uiso 1 calc R . H4C_1 H 0.1045(30) 0.3337(13) 0.5291(36) 0.067 Uiso 1 calc R . C5_1 C 0.1433(6) 0.4820(5) 0.2073(9) 0.036(2) Uani 1 d . . H5A_1 H 0.0668(6) 0.4887(5) 0.1741(9) 0.044 Uiso 1 calc R . H5B_1 H 0.1598(6) 0.5357(5) 0.2794(9) 0.044 Uiso 1 calc R . C6_1 C 0.2121(6) 0.4809(5) 0.0462(9) 0.034(2) Uani 1 d . . C7_1 C 0.1951(6) 0.5709(5) -0.0583(10) 0.047(2) Uani 1 d . . H7A_1 H 0.2220(36) 0.6224(8) 0.0076(28) 0.070 Uiso 1 calc R . H7B_1 H 0.1186(7) 0.5830(18) -0.0820(54) 0.070 Uiso 1 calc R . H7C_1 H 0.2338(32) 0.5646(13) -0.1668(29) 0.070 Uiso 1 calc R . C8_1 C 0.3301(5) 0.4716(4) 0.0971(9) 0.031(2) Uani 1 d . . H8A_1 H 0.3746(5) 0.4712(4) -0.0073(9) 0.037 Uiso 1 calc R . H8B_1 H 0.3482(5) 0.5253(4) 0.1679(9) 0.037 Uiso 1 calc R . C9_1 C 0.1868(6) 0.3973(5) -0.0650(8) 0.035(2) Uani 1 d . . H9A_1 H 0.2304(6) 0.3969(5) -0.1704(8) 0.042 Uiso 1 calc R . H9B_1 H 0.1104(6) 0.4020(5) -0.0994(8) 0.042 Uiso 1 calc R . C10_1 C 0.2109(6) 0.3070(4) 0.0350(8) 0.031(2) Uani 1 d . . C11_1 C 0.1911(7) 0.2239(5) -0.0766(10) 0.046(2) Uani 1 d . . H11A_1 H 0.2042(38) 0.1672(5) -0.0094(20) 0.069 Uiso 1 calc R . H11B_1 H 0.2394(27) 0.2228(19) -0.1750(34) 0.069 Uiso 1 calc R . H11C_1 H 0.1168(12) 0.2278(17) -0.1176(51) 0.069 Uiso 1 calc R . C12_1 C 0.1422(6) 0.3090(5) 0.1966(9) 0.036(2) Uani 1 d . . H12A_1 H 0.1576(6) 0.2514(5) 0.2627(9) 0.043 Uiso 1 calc R . H12B_1 H 0.0657(6) 0.3116(5) 0.1631(9) 0.043 Uiso 1 calc R . C13_1 C 0.3275(6) 0.3021(4) 0.0890(8) 0.032(2) Uani 1 d . . H13A_1 H 0.3436(6) 0.2445(4) 0.1546(8) 0.039 Uiso 1 calc R . H13B_1 H 0.3729(6) 0.3000(4) -0.0145(8) 0.039 Uiso 1 calc R . Cl1_2 Cl 0.46913(14) 0.87742(12) -0.2085(2) 0.0351(5) Uani 1 d . . O1_2 O 0.3061(4) 0.8039(3) 0.0408(6) 0.0338(12) Uani 1 d . . H1_2 H 0.3645(62) 0.8226(51) -0.0372(94) 0.050(11) Uiso 1 d . . O2_2 O 0.3055(4) 0.9637(3) 0.0380(6) 0.0336(12) Uani 1 d . . H2_2 H 0.3555(64) 0.9426(54) -0.0313(97) 0.050(11) Uiso 1 d . . N1_2 N 0.3532(4) 0.8831(3) 0.2988(7) 0.0270(13) Uani 1 d . . C1_2 C 0.4707(6) 0.8760(5) 0.2579(9) 0.038(2) Uani 1 d . . H1F_2 H 0.5124(6) 0.8758(31) 0.3649(9) 0.057 Uiso 1 calc R . H1G_2 H 0.4884(9) 0.9290(16) 0.1877(48) 0.057 Uiso 1 calc R . H1H_2 H 0.4877(9) 0.8187(15) 0.1946(49) 0.057 Uiso 1 calc R . C2_2 C 0.2819(5) 0.8865(4) 0.1260(8) 0.0280(15) Uani 1 d . . C3_2 C 0.1636(5) 0.8924(5) 0.1810(8) 0.032(2) Uani 1 d . . C4_2 C 0.0932(6) 0.8932(5) 0.0198(9) 0.044(2) Uani 1 d . . H4D_2 H 0.0177(6) 0.8980(35) 0.0528(9) 0.066 Uiso 1 calc R . H4E_2 H 0.1078(29) 0.8359(15) -0.0448(33) 0.066 Uiso 1 calc R . H4F_2 H 0.1088(28) 0.9462(19) -0.0519(31) 0.066 Uiso 1 calc R . C5_2 C 0.1436(6) 0.9810(5) 0.2857(8) 0.032(2) Uani 1 d . . H5C_2 H 0.1599(6) 1.0348(5) 0.2142(8) 0.039 Uiso 1 calc R . H5D_2 H 0.0671(6) 0.9878(5) 0.3168(8) 0.039 Uiso 1 calc R . C6_2 C 0.2119(6) 0.9809(5) 0.4491(8) 0.034(2) Uani 1 d . . C7_2 C 0.1938(7) 1.0702(5) 0.5514(10) 0.052(2) Uani 1 d . . H7D_2 H 0.2354(33) 1.0656(15) 0.6584(32) 0.078 Uiso 1 calc R . H7E_2 H 0.1177(9) 1.0800(19) 0.5778(58) 0.078 Uiso 1 calc R . H7F_2 H 0.2169(39) 1.1222(7) 0.4835(28) 0.078 Uiso 1 calc R . C8_2 C 0.3288(5) 0.9708(4) 0.4003(8) 0.029(2) Uani 1 d . . H8C_2 H 0.3471(5) 1.0248(4) 0.3309(8) 0.034 Uiso 1 calc R . H8D_2 H 0.3735(5) 0.9697(4) 0.5056(8) 0.034 Uiso 1 calc R . C9_2 C 0.1861(6) 0.8970(5) 0.5585(8) 0.032(2) Uani 1 d . . H9C_2 H 0.1097(6) 0.9018(5) 0.5909(8) 0.039 Uiso 1 calc R . H9D_2 H 0.2296(6) 0.8960(5) 0.6651(8) 0.039 Uiso 1 calc R . C10_2 C 0.2101(6) 0.8069(4) 0.4571(9) 0.032(2) Uani 1 d . . C11_2 C 0.1908(7) 0.7239(5) 0.5733(9) 0.044(2) Uani 1 d . . H11D_2 H 0.2041(37) 0.6665(5) 0.5085(20) 0.066 Uiso 1 calc R . H11E_2 H 0.1167(12) 0.7280(18) 0.6131(49) 0.066 Uiso 1 calc R . H11F_2 H 0.2395(26) 0.7243(19) 0.6723(32) 0.066 Uiso 1 calc R . C12_2 C 0.1415(6) 0.8086(5) 0.2956(9) 0.035(2) Uani 1 d . . H12C_2 H 0.0651(6) 0.8115(5) 0.3276(9) 0.042 Uiso 1 calc R . H12D_2 H 0.1566(6) 0.7508(5) 0.2302(9) 0.042 Uiso 1 calc R . C13_2 C 0.3279(6) 0.8014(4) 0.4066(8) 0.030(2) Uani 1 d . . H13C_2 H 0.3731(6) 0.7998(4) 0.5114(8) 0.036 Uiso 1 calc R . H13D_2 H 0.3443(6) 0.7438(4) 0.3415(8) 0.036 Uiso 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 Cl1_1 0.0392(11) 0.0325(10) 0.0345(10) -0.0019(7) -0.0057(8) 0.0013(8) O1_1 0.043(3) 0.025(3) 0.031(3) 0.003(2) -0.007(2) -0.006(2) O2_1 0.038(3) 0.030(3) 0.034(3) -0.008(2) -0.011(2) 0.002(2) N1_1 0.032(3) 0.025(3) 0.027(3) -0.002(2) -0.002(2) -0.001(3) C1_1 0.038(5) 0.020(4) 0.039(4) 0.005(3) -0.007(3) 0.002(3) C2_1 0.039(4) 0.024(4) 0.028(4) 0.000(3) 0.000(3) -0.001(3) C3_1 0.028(4) 0.032(4) 0.034(4) 0.003(3) -0.002(3) -0.003(3) C4_1 0.034(5) 0.056(5) 0.045(5) 0.003(4) 0.000(4) -0.004(4) C5_1 0.029(4) 0.034(4) 0.047(5) -0.002(3) -0.001(3) 0.002(3) C6_1 0.038(4) 0.025(4) 0.039(4) 0.005(3) -0.005(3) -0.002(3) C7_1 0.050(5) 0.035(4) 0.053(5) 0.009(4) -0.013(4) 0.004(4) C8_1 0.035(4) 0.021(4) 0.036(4) 0.007(3) -0.004(3) -0.001(3) C9_1 0.043(5) 0.036(4) 0.027(4) 0.003(3) -0.005(3) -0.008(3) C10_1 0.041(4) 0.022(4) 0.031(4) 0.001(3) -0.008(3) -0.003(3) C11_1 0.055(5) 0.037(5) 0.047(5) -0.010(4) -0.005(4) -0.013(4) C12_1 0.032(4) 0.035(4) 0.041(4) 0.004(3) -0.011(3) -0.011(3) C13_1 0.049(5) 0.016(4) 0.031(4) -0.007(3) -0.003(3) -0.005(3) Cl1_2 0.0364(11) 0.0352(11) 0.0336(10) 0.0018(8) 0.0048(8) -0.0003(8) O1_2 0.042(3) 0.031(3) 0.029(3) -0.004(2) 0.006(2) -0.003(2) O2_2 0.040(3) 0.029(3) 0.032(3) 0.008(2) 0.007(2) 0.002(2) N1_2 0.033(3) 0.018(3) 0.030(3) 0.002(2) 0.001(2) -0.001(2) C1_2 0.041(5) 0.034(4) 0.040(5) -0.001(3) -0.002(3) 0.000(3) C2_2 0.031(4) 0.026(4) 0.026(4) -0.003(3) 0.002(3) 0.002(3) C3_2 0.028(4) 0.037(4) 0.032(4) -0.007(3) -0.004(3) -0.003(3) C4_2 0.037(5) 0.052(5) 0.043(5) -0.001(4) -0.006(3) 0.000(4) C5_2 0.030(4) 0.028(4) 0.039(4) 0.009(3) 0.003(3) 0.002(3) C6_2 0.045(5) 0.025(4) 0.032(4) -0.004(3) 0.004(3) -0.001(3) C7_2 0.065(6) 0.035(5) 0.055(5) -0.014(4) 0.017(4) -0.001(4) C8_2 0.040(4) 0.015(3) 0.031(4) -0.003(3) -0.003(3) -0.002(3) C9_2 0.034(4) 0.037(4) 0.026(4) 0.002(3) 0.002(3) -0.004(3) C10_2 0.041(4) 0.023(4) 0.034(4) 0.000(3) 0.006(3) -0.006(3) C11_2 0.060(5) 0.029(4) 0.043(5) 0.008(3) 0.003(4) -0.012(4) C12_2 0.029(4) 0.035(4) 0.040(4) -0.003(3) 0.006(3) -0.006(3) C13_2 0.042(4) 0.019(4) 0.029(4) 0.005(3) 0.006(3) -0.002(3) _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_1 H1_1 2.08(8) . ? Cl1_1 H2_1 2.20(8) . ? O1_1 C2_1 1.374(8) . ? O1_1 H1_1 1.01(8) . ? O2_1 C2_1 1.371(8) . ? O2_1 H2_1 0.92(8) . ? N1_1 C1_1 1.491(8) . ? N1_1 C13_1 1.502(8) . ? N1_1 C8_1 1.515(8) . ? N1_1 C2_1 1.615(8) . ? C1_1 H1B_1 0.98 . ? C1_1 H1C_1 0.98 . ? C1_1 H1D_1 0.98 . ? C2_1 C3_1 1.552(9) . ? C3_1 C4_1 1.527(9) . ? C3_1 C5_1 1.531(9) . ? C3_1 C12_1 1.542(9) . ? C4_1 H4A_1 0.98 . ? C4_1 H4B_1 0.98 . ? C4_1 H4C_1 0.98 . ? C5_1 C6_1 1.528(9) . ? C5_1 H5A_1 0.99 . ? C5_1 H5B_1 0.99 . ? C6_1 C8_1 1.527(9) . ? C6_1 C9_1 1.535(9) . ? C6_1 C7_1 1.543(9) . ? C7_1 H7A_1 0.98 . ? C7_1 H7B_1 0.98 . ? C7_1 H7C_1 0.98 . ? C8_1 H8A_1 0.99 . ? C8_1 H8B_1 0.99 . ? C9_1 C10_1 1.538(9) . ? C9_1 H9A_1 0.99 . ? C9_1 H9B_1 0.99 . ? C10_1 C13_1 1.515(10) . ? C10_1 C11_1 1.517(9) . ? C10_1 C12_1 1.531(10) . ? C11_1 H11A_1 0.98 . ? C11_1 H11B_1 0.98 . ? C11_1 H11C_1 0.98 . ? C12_1 H12A_1 0.99 . ? C12_1 H12B_1 0.99 . ? C13_1 H13A_1 0.99 . ? C13_1 H13B_1 0.99 . ? Cl1_2 H1_2 2.07(8) . ? Cl1_2 H2_2 2.17(8) . ? O1_2 C2_2 1.389(7) . ? O1_2 H1_2 1.00(8) . ? O2_2 C2_2 1.361(8) . ? O2_2 H2_2 0.87(8) . ? N1_2 C13_2 1.503(8) . ? N1_2 C1_2 1.506(9) . ? N1_2 C8_2 1.515(8) . ? N1_2 C2_2 1.609(8) . ? C1_2 H1F_2 0.98 . ? C1_2 H1G_2 0.98 . ? C1_2 H1H_2 0.98 . ? C2_2 C3_2 1.544(9) . ? C3_2 C4_2 1.529(9) . ? C3_2 C5_2 1.532(9) . ? C3_2 C12_2 1.547(10) . ? C4_2 H4D_2 0.98 . ? C4_2 H4E_2 0.98 . ? C4_2 H4F_2 0.98 . ? C5_2 C6_2 1.529(9) . ? C5_2 H5C_2 0.99 . ? C5_2 H5D_2 0.99 . ? C6_2 C8_2 1.515(9) . ? C6_2 C7_2 1.526(9) . ? C6_2 C9_2 1.537(9) . ? C7_2 H7D_2 0.98 . ? C7_2 H7E_2 0.98 . ? C7_2 H7F_2 0.98 . ? C8_2 H8C_2 0.99 . ? C8_2 H8D_2 0.99 . ? C9_2 C10_2 1.543(9) . ? C9_2 H9C_2 0.99 . ? C9_2 H9D_2 0.99 . ? C10_2 C12_2 1.517(9) . ? C10_2 C13_2 1.529(9) . ? C10_2 C11_2 1.538(9) . ? C11_2 H11D_2 0.98 . ? C11_2 H11E_2 0.98 . ? C11_2 H11F_2 0.98 . ? C12_2 H12C_2 0.99 . ? C12_2 H12D_2 0.99 . ? C13_2 H13C_2 0.99 . ? C13_2 H13D_2 0.99 . ? 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 H1_1 Cl1_1 H2_1 56.6(27) . . ? C2_1 O1_1 H1_1 107.6(42) . . ? C2_1 O2_1 H2_1 110.7(47) . . ? C1_1 N1_1 C13_1 108.9(5) . . ? C1_1 N1_1 C8_1 109.1(5) . . ? C13_1 N1_1 C8_1 109.3(5) . . ? C1_1 N1_1 C2_1 111.1(5) . . ? C13_1 N1_1 C2_1 109.3(5) . . ? C8_1 N1_1 C2_1 109.2(5) . . ? N1_1 C1_1 H1B_1 109.5(3) . . ? N1_1 C1_1 H1C_1 109.5(3) . . ? H1B_1 C1_1 H1C_1 109.5 . . ? N1_1 C1_1 H1D_1 109.5(3) . . ? H1B_1 C1_1 H1D_1 109.5 . . ? H1C_1 C1_1 H1D_1 109.5 . . ? O2_1 C2_1 O1_1 115.0(5) . . ? O2_1 C2_1 C3_1 109.2(5) . . ? O1_1 C2_1 C3_1 110.9(5) . . ? O2_1 C2_1 N1_1 106.9(5) . . ? O1_1 C2_1 N1_1 107.4(5) . . ? C3_1 C2_1 N1_1 107.1(5) . . ? C4_1 C3_1 C5_1 110.9(6) . . ? C4_1 C3_1 C12_1 110.2(6) . . ? C5_1 C3_1 C12_1 109.6(6) . . ? C4_1 C3_1 C2_1 108.3(6) . . ? C5_1 C3_1 C2_1 109.0(5) . . ? C12_1 C3_1 C2_1 108.7(5) . . ? C3_1 C4_1 H4A_1 109.5(4) . . ? C3_1 C4_1 H4B_1 109.5(4) . . ? H4A_1 C4_1 H4B_1 109.5 . . ? C3_1 C4_1 H4C_1 109.5(4) . . ? H4A_1 C4_1 H4C_1 109.5 . . ? H4B_1 C4_1 H4C_1 109.5 . . ? C6_1 C5_1 C3_1 110.9(6) . . ? C6_1 C5_1 H5A_1 109.5(4) . . ? C3_1 C5_1 H5A_1 109.5(4) . . ? C6_1 C5_1 H5B_1 109.5(4) . . ? C3_1 C5_1 H5B_1 109.5(4) . . ? H5A_1 C5_1 H5B_1 108.1 . . ? C8_1 C6_1 C5_1 109.6(6) . . ? C8_1 C6_1 C9_1 108.3(6) . . ? C5_1 C6_1 C9_1 109.4(6) . . ? C8_1 C6_1 C7_1 107.1(6) . . ? C5_1 C6_1 C7_1 112.1(6) . . ? C9_1 C6_1 C7_1 110.3(6) . . ? C6_1 C7_1 H7A_1 109.5(4) . . ? C6_1 C7_1 H7B_1 109.5(4) . . ? H7A_1 C7_1 H7B_1 109.5 . . ? C6_1 C7_1 H7C_1 109.5(4) . . ? H7A_1 C7_1 H7C_1 109.5 . . ? H7B_1 C7_1 H7C_1 109.5 . . ? N1_1 C8_1 C6_1 110.7(5) . . ? N1_1 C8_1 H8A_1 109.5(3) . . ? C6_1 C8_1 H8A_1 109.5(4) . . ? N1_1 C8_1 H8B_1 109.5(3) . . ? C6_1 C8_1 H8B_1 109.5(4) . . ? H8A_1 C8_1 H8B_1 108.1 . . ? C6_1 C9_1 C10_1 110.4(5) . . ? C6_1 C9_1 H9A_1 109.6(4) . . ? C10_1 C9_1 H9A_1 109.6(4) . . ? C6_1 C9_1 H9B_1 109.6(4) . . ? C10_1 C9_1 H9B_1 109.6(4) . . ? H9A_1 C9_1 H9B_1 108.1 . . ? C13_1 C10_1 C11_1 108.5(6) . . ? C13_1 C10_1 C12_1 108.5(5) . . ? C11_1 C10_1 C12_1 111.7(6) . . ? C13_1 C10_1 C9_1 108.7(6) . . ? C11_1 C10_1 C9_1 110.7(6) . . ? C12_1 C10_1 C9_1 108.6(6) . . ? C10_1 C11_1 H11A_1 109.5(4) . . ? C10_1 C11_1 H11B_1 109.5(4) . . ? H11A_1 C11_1 H11B_1 109.5 . . ? C10_1 C11_1 H11C_1 109.5(4) . . ? H11A_1 C11_1 H11C_1 109.5 . . ? H11B_1 C11_1 H11C_1 109.5 . . ? C10_1 C12_1 C3_1 111.4(6) . . ? C10_1 C12_1 H12A_1 109.4(4) . . ? C3_1 C12_1 H12A_1 109.4(4) . . ? C10_1 C12_1 H12B_1 109.4(4) . . ? C3_1 C12_1 H12B_1 109.4(4) . . ? H12A_1 C12_1 H12B_1 108.0 . . ? N1_1 C13_1 C10_1 112.0(5) . . ? N1_1 C13_1 H13A_1 109.2(3) . . ? C10_1 C13_1 H13A_1 109.2(4) . . ? N1_1 C13_1 H13B_1 109.2(3) . . ? C10_1 C13_1 H13B_1 109.2(4) . . ? H13A_1 C13_1 H13B_1 107.9 . . ? H1_2 Cl1_2 H2_2 48.3(27) . . ? C2_2 O1_2 H1_2 100.8(43) . . ? C2_2 O2_2 H2_2 102.3(52) . . ? C13_2 N1_2 C1_2 108.5(5) . . ? C13_2 N1_2 C8_2 109.0(5) . . ? C1_2 N1_2 C8_2 108.8(5) . . ? C13_2 N1_2 C2_2 110.5(5) . . ? C1_2 N1_2 C2_2 111.0(5) . . ? C8_2 N1_2 C2_2 108.9(5) . . ? N1_2 C1_2 H1F_2 109.5(3) . . ? N1_2 C1_2 H1G_2 109.5(3) . . ? H1F_2 C1_2 H1G_2 109.5 . . ? N1_2 C1_2 H1H_2 109.5(3) . . ? H1F_2 C1_2 H1H_2 109.5 . . ? H1G_2 C1_2 H1H_2 109.5 . . ? O2_2 C2_2 O1_2 114.8(5) . . ? O2_2 C2_2 C3_2 110.6(5) . . ? O1_2 C2_2 C3_2 110.3(5) . . ? O2_2 C2_2 N1_2 107.5(5) . . ? O1_2 C2_2 N1_2 106.2(5) . . ? C3_2 C2_2 N1_2 107.1(5) . . ? C4_2 C3_2 C5_2 111.2(6) . . ? C4_2 C3_2 C2_2 108.6(6) . . ? C5_2 C3_2 C2_2 108.0(5) . . ? C4_2 C3_2 C12_2 110.6(6) . . ? C5_2 C3_2 C12_2 108.8(6) . . ? C2_2 C3_2 C12_2 109.6(5) . . ? C3_2 C4_2 H4D_2 109.5(4) . . ? C3_2 C4_2 H4E_2 109.5(4) . . ? H4D_2 C4_2 H4E_2 109.5 . . ? C3_2 C4_2 H4F_2 109.5(4) . . ? H4D_2 C4_2 H4F_2 109.5 . . ? H4E_2 C4_2 H4F_2 109.5 . . ? C6_2 C5_2 C3_2 112.1(5) . . ? C6_2 C5_2 H5C_2 109.2(4) . . ? C3_2 C5_2 H5C_2 109.2(4) . . ? C6_2 C5_2 H5D_2 109.2(4) . . ? C3_2 C5_2 H5D_2 109.2(4) . . ? H5C_2 C5_2 H5D_2 107.9 . . ? C8_2 C6_2 C7_2 108.3(6) . . ? C8_2 C6_2 C5_2 108.9(5) . . ? C7_2 C6_2 C5_2 112.1(6) . . ? C8_2 C6_2 C9_2 108.2(5) . . ? C7_2 C6_2 C9_2 110.6(6) . . ? C5_2 C6_2 C9_2 108.7(6) . . ? C6_2 C7_2 H7D_2 109.5(4) . . ? C6_2 C7_2 H7E_2 109.5(4) . . ? H7D_2 C7_2 H7E_2 109.5 . . ? C6_2 C7_2 H7F_2 109.5(4) . . ? H7D_2 C7_2 H7F_2 109.5 . . ? H7E_2 C7_2 H7F_2 109.5 . . ? N1_2 C8_2 C6_2 111.4(5) . . ? N1_2 C8_2 H8C_2 109.3(3) . . ? C6_2 C8_2 H8C_2 109.3(3) . . ? N1_2 C8_2 H8D_2 109.3(3) . . ? C6_2 C8_2 H8D_2 109.3(4) . . ? H8C_2 C8_2 H8D_2 108.0 . . ? C6_2 C9_2 C10_2 110.2(5) . . ? C6_2 C9_2 H9C_2 109.6(4) . . ? C10_2 C9_2 H9C_2 109.6(4) . . ? C6_2 C9_2 H9D_2 109.6(4) . . ? C10_2 C9_2 H9D_2 109.6(4) . . ? H9C_2 C9_2 H9D_2 108.1 . . ? C12_2 C10_2 C13_2 109.0(6) . . ? C12_2 C10_2 C11_2 112.8(6) . . ? C13_2 C10_2 C11_2 108.0(6) . . ? C12_2 C10_2 C9_2 109.1(6) . . ? C13_2 C10_2 C9_2 108.7(5) . . ? C11_2 C10_2 C9_2 109.1(6) . . ? C10_2 C11_2 H11D_2 109.5(4) . . ? C10_2 C11_2 H11E_2 109.5(4) . . ? H11D_2 C11_2 H11E_2 109.5 . . ? C10_2 C11_2 H11F_2 109.5(4) . . ? H11D_2 C11_2 H11F_2 109.5 . . ? H11E_2 C11_2 H11F_2 109.5 . . ? C10_2 C12_2 C3_2 111.4(6) . . ? C10_2 C12_2 H12C_2 109.3(4) . . ? C3_2 C12_2 H12C_2 109.3(4) . . ? C10_2 C12_2 H12D_2 109.3(4) . . ? C3_2 C12_2 H12D_2 109.3(4) . . ? H12C_2 C12_2 H12D_2 108.0 . . ? N1_2 C13_2 C10_2 110.7(5) . . ? N1_2 C13_2 H13C_2 109.5(3) . . ? C10_2 C13_2 H13C_2 109.5(4) . . ? N1_2 C13_2 H13D_2 109.5(3) . . ? C10_2 C13_2 H13D_2 109.5(3) . . ? H13C_2 C13_2 H13D_2 108.1 . . ? 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 Cl1_1 H2_1 O2_1 C2_1 -56.2(129) . . . . ? H2_1 O2_1 C2_1 C3_1 164.7(50) . . . . ? Cl1_1 H2_1 O2_1 C2_1 -56.2(129) . . . . ? H2_1 O2_1 C2_1 N1_1 -79.8(50) . . . . ? Cl1_1 H1_1 O1_1 C2_1 18.4(230) . . . . ? H1_1 O1_1 C2_1 C3_1 -149.5(44) . . . . ? Cl1_1 H1_1 O1_1 C2_1 18.4(230) . . . . ? H1_1 O1_1 C2_1 N1_1 93.8(44) . . . . ? Cl1_2 H2_2 O2_2 C2_2 43.1(651) . . . . ? H2_2 O2_2 C2_2 C3_2 -149.7(53) . . . . ? Cl1_2 H2_2 O2_2 C2_2 43.1(651) . . . . ? H2_2 O2_2 C2_2 N1_2 93.7(53) . . . . ? Cl1_2 H1_2 O1_2 C2_2 -50.9(417) . . . . ? H1_2 O1_2 C2_2 C3_2 151.1(43) . . . . ? Cl1_2 H1_2 O1_2 C2_2 -50.9(417) . . . . ? H1_2 O1_2 C2_2 N1_2 -93.3(43) . . . . ? H2_1 O2_1 C2_1 O1_1 39.3(51) . . . . ? H1_1 O1_1 C2_1 O2_1 -25.0(45) . . . . ? H2_2 O2_2 C2_2 O1_2 -24.2(54) . . . . ? H1_2 O1_2 C2_2 O2_2 25.4(43) . . . . ? _refine_diff_density_max 0.311 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.080