# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Polly Louise Arnold' 'Alexander J. Blake' 'Kate Davis' 'Mark Rodden' 'Andrew C. Scarisbrick' 'Claire Wilson' _publ_contact_author_name 'Dr Polly Louise Arnold' _publ_contact_author_address ; School of Chemistry University of Nottingham University Park Nottingham NG7 2RD UNITED KINGDOM ; _publ_contact_author_email POLLY.ARNOLD@NOTTINGHAM.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Asymmetric Lithium(I) and copper(II) alkoxy-N-heterocyclic carbene complexes; crystallographic characterisation and Lewis acid catalysis ; data_imiohi _database_code_depnum_ccdc_archive 'CCDC 235713' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H19 I N2 O' _chemical_formula_weight 310.17 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' I I -0.4742 1.8119 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.297(2) _cell_length_b 11.516(2) _cell_length_c 11.439(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.408(3) _cell_angle_gamma 90.00 _cell_volume 1356.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3707 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 2.338 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.455 _exptl_absorpt_correction_T_max 0.649 _exptl_absorpt_process_details 'Bruker SHELXTL v6.12' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8287 _diffrn_reflns_av_R_equivalents 0.033 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3074 _reflns_number_gt 2379 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'enCIFer (CCDC, 2003); PLATON (Spek, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0155P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geometrically placed, OH & Me from delta-F' _refine_ls_hydrogen_treatment 'riding model, OH & Me as rigid rotors' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3074 _refine_ls_number_parameters 132 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0282 _refine_ls_R_factor_gt 0.0214 _refine_ls_wR_factor_ref 0.0444 _refine_ls_wR_factor_gt 0.0437 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.005 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I I 0.747508(14) -0.004912(11) 0.712604(13) 0.03035(6) Uani 1 1 d . . . O1 O 0.52220(14) 0.16998(12) 0.57243(14) 0.0317(4) Uani 1 1 d . . . H1A H 0.5922 0.1382 0.5927 0.047 Uiso 1 1 calc R . . N1 N 0.79186(17) -0.01340(13) 0.33715(16) 0.0264(4) Uani 1 1 d . . . C1 C 0.6743(2) 0.02731(16) 0.35970(18) 0.0252(5) Uani 1 1 d . . . H1B H 0.5996 -0.0184 0.3751 0.030 Uiso 1 1 calc R . . N2 N 0.67820(16) 0.14258(13) 0.35725(14) 0.0232(4) Uani 1 1 d . . . C2 C 0.8747(2) 0.07902(17) 0.32105(19) 0.0296(5) Uani 1 1 d . . . H2A H 0.9649 0.0750 0.3045 0.036 Uiso 1 1 calc R . . C3 C 0.8032(2) 0.17632(18) 0.33322(19) 0.0285(5) Uani 1 1 d . . . H3A H 0.8336 0.2539 0.3264 0.034 Uiso 1 1 calc R . . C4 C 0.8258(2) -0.13809(17) 0.3237(2) 0.0326(6) Uani 1 1 d . . . H4A H 0.7442 -0.1848 0.3288 0.039 Uiso 1 1 calc R . . C5 C 0.8846(2) -0.15707(18) 0.20427(19) 0.0368(6) Uani 1 1 d . . . H5A H 0.8280 -0.1227 0.1444 0.055 Uiso 1 1 calc R . . H5B H 0.8934 -0.2405 0.1897 0.055 Uiso 1 1 calc R . . H5C H 0.9703 -0.1203 0.2014 0.055 Uiso 1 1 calc R . . C6 C 0.9161(3) -0.17573(19) 0.4217(2) 0.0462(7) Uani 1 1 d . . . H6A H 0.8773 -0.1560 0.4971 0.069 Uiso 1 1 calc R . . H6B H 0.9996 -0.1357 0.4140 0.069 Uiso 1 1 calc R . . H6C H 0.9299 -0.2598 0.4174 0.069 Uiso 1 1 calc R . . C7 C 0.5661(2) 0.21970(17) 0.37115(18) 0.0262(5) Uani 1 1 d . . . H7A H 0.4865 0.1773 0.3476 0.031 Uiso 1 1 calc R . . H7B H 0.5758 0.2867 0.3177 0.031 Uiso 1 1 calc R . . C8 C 0.5491(2) 0.26497(17) 0.49572(18) 0.0262(5) Uani 1 1 d . . . C9 C 0.4269(2) 0.33921(19) 0.4944(2) 0.0385(6) Uani 1 1 d . . . H9A H 0.3525 0.2916 0.4702 0.058 Uiso 1 1 calc R . . H9B H 0.4378 0.4035 0.4393 0.058 Uiso 1 1 calc R . . H9C H 0.4118 0.3703 0.5729 0.058 Uiso 1 1 calc R . . C10 C 0.6662(2) 0.33296(18) 0.53840(19) 0.0334(6) Uani 1 1 d . . . H10A H 0.6466 0.3688 0.6140 0.050 Uiso 1 1 calc R . . H10B H 0.6872 0.3936 0.4815 0.050 Uiso 1 1 calc R . . H10C H 0.7405 0.2804 0.5473 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I 0.02880(9) 0.02697(8) 0.03527(9) -0.00106(7) 0.00071(6) 0.00105(7) O1 0.0311(9) 0.0320(8) 0.0320(9) 0.0101(7) 0.0034(7) 0.0000(7) N1 0.0268(10) 0.0224(9) 0.0299(10) -0.0020(8) 0.0035(8) -0.0015(7) C1 0.0258(12) 0.0244(11) 0.0254(12) -0.0006(9) 0.0045(9) -0.0038(8) N2 0.0240(10) 0.0227(9) 0.0231(10) -0.0016(7) 0.0026(8) -0.0022(7) C2 0.0234(12) 0.0258(11) 0.0396(15) -0.0013(10) 0.0037(10) -0.0046(9) C3 0.0243(12) 0.0241(11) 0.0372(14) -0.0019(10) 0.0015(10) -0.0053(9) C4 0.0355(14) 0.0201(11) 0.0421(15) -0.0024(10) 0.0056(12) -0.0014(9) C5 0.0419(15) 0.0310(12) 0.0376(14) -0.0126(11) -0.0006(12) 0.0030(10) C6 0.0632(19) 0.0371(14) 0.0383(15) 0.0071(12) 0.0037(14) 0.0118(13) C7 0.0239(12) 0.0276(11) 0.0272(12) 0.0007(9) -0.0016(10) 0.0012(9) C8 0.0292(12) 0.0239(11) 0.0257(12) 0.0036(9) 0.0029(10) 0.0018(9) C9 0.0383(15) 0.0394(13) 0.0380(15) 0.0040(11) 0.0081(12) 0.0140(11) C10 0.0436(15) 0.0307(12) 0.0258(13) -0.0021(10) -0.0010(11) -0.0028(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8 1.431(2) . ? N1 C1 1.325(3) . ? N1 C2 1.377(2) . ? N1 C4 1.486(2) . ? C1 N2 1.328(2) . ? N2 C3 1.374(2) . ? N2 C7 1.466(2) . ? C2 C3 1.349(3) . ? C4 C5 1.514(3) . ? C4 C6 1.514(3) . ? C7 C8 1.528(3) . ? C8 C10 1.516(3) . ? C8 C9 1.521(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 108.68(16) . . ? C1 N1 C4 125.30(17) . . ? C2 N1 C4 125.91(18) . . ? N1 C1 N2 108.77(18) . . ? C1 N2 C3 108.38(17) . . ? C1 N2 C7 125.39(17) . . ? C3 N2 C7 126.15(16) . . ? C3 C2 N1 106.81(19) . . ? C2 C3 N2 107.37(18) . . ? N1 C4 C5 109.17(17) . . ? N1 C4 C6 110.11(19) . . ? C5 C4 C6 112.3(2) . . ? N2 C7 C8 113.77(18) . . ? O1 C8 C10 110.76(18) . . ? O1 C8 C9 105.79(17) . . ? C10 C8 C9 111.65(18) . . ? O1 C8 C7 109.57(16) . . ? C10 C8 C7 112.37(17) . . ? C9 C8 C7 106.42(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 O1 H1A I 0.84 2.67 3.4578(15) 157.1 . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.577 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.069 data_imiohi_b _database_code_depnum_ccdc_archive 'CCDC 235714' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H19 I N2 O' _chemical_formula_weight 310.17 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' I I -0.4742 1.8119 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.297(2) _cell_length_b 11.516(2) _cell_length_c 11.439(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.408(3) _cell_angle_gamma 90.00 _cell_volume 1356.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3707 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 2.338 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.455 _exptl_absorpt_correction_T_max 0.649 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3074 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3074 _reflns_number_gt 2379 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'enCIFer (CCDC, 2003); PLATON (Spek, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0255P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3074 _refine_ls_number_parameters 132 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0278 _refine_ls_R_factor_gt 0.0210 _refine_ls_wR_factor_ref 0.0481 _refine_ls_wR_factor_gt 0.0471 _refine_ls_goodness_of_fit_ref 0.896 _refine_ls_restrained_S_all 0.896 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I I 0.747504(13) -0.004917(10) 0.712608(12) 0.03007(6) Uani 1 1 d . . . O1 O 0.52224(13) 0.16999(11) 0.57244(13) 0.0316(3) Uani 1 1 d . . . H1A H 0.5906 0.1386 0.5918 0.047 Uiso 1 1 calc R . . N2 N 0.67822(15) 0.14259(12) 0.35724(14) 0.0232(4) Uani 1 1 d . . . N1 N 0.79180(17) -0.01342(12) 0.33710(16) 0.0264(4) Uani 1 1 d . . . C4 C 0.8259(2) -0.13811(16) 0.32373(19) 0.0326(5) Uani 1 1 d . . . H4A H 0.7459 -0.1839 0.3286 0.039 Uiso 1 1 calc R . . C7 C 0.56615(19) 0.21973(16) 0.37118(17) 0.0261(4) Uani 1 1 d . . . H7A H 0.4882 0.1782 0.3480 0.031 Uiso 1 1 calc R . . H7B H 0.5757 0.2854 0.3189 0.031 Uiso 1 1 calc R . . C8 C 0.5491(2) 0.26491(17) 0.49560(17) 0.0262(4) Uani 1 1 d . . . C1 C 0.6743(2) 0.02741(15) 0.35958(18) 0.0252(4) Uani 1 1 d . . . H1B H 0.6011 -0.0173 0.3745 0.030 Uiso 1 1 calc R . . C10 C 0.6662(2) 0.33293(17) 0.53840(18) 0.0336(5) Uani 1 1 d . . . H10A H 0.6473 0.3674 0.6128 0.050 Uiso 1 1 calc R . . H10B H 0.6864 0.3928 0.4830 0.050 Uiso 1 1 calc R . . H10C H 0.7392 0.2816 0.5465 0.050 Uiso 1 1 calc R . . C3 C 0.80327(19) 0.17632(17) 0.33319(18) 0.0286(5) Uani 1 1 d . . . H3A H 0.8331 0.2522 0.3265 0.034 Uiso 1 1 calc R . . C6 C 0.9161(2) -0.17574(19) 0.4216(2) 0.0463(6) Uani 1 1 d . . . H6A H 0.8778 -0.1570 0.4955 0.069 Uiso 1 1 calc R . . H6B H 0.9976 -0.1360 0.4145 0.069 Uiso 1 1 calc R . . H6C H 0.9301 -0.2580 0.4169 0.069 Uiso 1 1 calc R . . C2 C 0.8747(2) 0.07905(16) 0.32102(18) 0.0296(5) Uani 1 1 d . . . H2A H 0.9630 0.0751 0.3049 0.036 Uiso 1 1 calc R . . C9 C 0.4270(2) 0.33927(19) 0.49445(19) 0.0386(6) Uani 1 1 d . . . H9A H 0.3542 0.2930 0.4698 0.058 Uiso 1 1 calc R . . H9B H 0.4380 0.4029 0.4412 0.058 Uiso 1 1 calc R . . H9C H 0.4116 0.3689 0.5716 0.058 Uiso 1 1 calc R . . C5 C 0.8846(2) -0.15706(17) 0.20429(19) 0.0369(5) Uani 1 1 d . . . H5A H 0.8292 -0.1234 0.1456 0.055 Uiso 1 1 calc R . . H5B H 0.8933 -0.2388 0.1900 0.055 Uiso 1 1 calc R . . H5C H 0.9686 -0.1210 0.2015 0.055 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I 0.02853(9) 0.02661(8) 0.03508(9) -0.00105(6) 0.00078(6) 0.00106(6) O1 0.0310(8) 0.0321(8) 0.0317(9) 0.0101(7) 0.0036(7) 0.0002(6) N2 0.0238(9) 0.0226(8) 0.0233(9) -0.0015(7) 0.0027(7) -0.0024(7) N1 0.0267(10) 0.0230(9) 0.0297(9) -0.0021(7) 0.0036(7) -0.0012(7) C4 0.0360(13) 0.0204(10) 0.0416(14) -0.0021(9) 0.0057(11) -0.0019(9) C7 0.0237(11) 0.0278(10) 0.0268(11) 0.0011(9) -0.0015(9) 0.0011(8) C8 0.0288(11) 0.0238(10) 0.0260(11) 0.0036(8) 0.0028(9) 0.0023(9) C1 0.0253(11) 0.0247(10) 0.0257(11) -0.0007(8) 0.0045(9) -0.0035(8) C10 0.0440(14) 0.0306(11) 0.0262(12) -0.0021(9) -0.0011(10) -0.0029(10) C3 0.0237(11) 0.0244(10) 0.0377(13) -0.0022(9) 0.0017(9) -0.0049(8) C6 0.0628(18) 0.0372(13) 0.0390(14) 0.0075(11) 0.0039(13) 0.0121(12) C2 0.0231(11) 0.0257(10) 0.0401(13) -0.0010(9) 0.0037(9) -0.0046(8) C9 0.0386(15) 0.0391(12) 0.0382(14) 0.0037(10) 0.0078(11) 0.0138(11) C5 0.0419(14) 0.0303(11) 0.0384(13) -0.0127(10) -0.0006(11) 0.0027(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8 1.431(2) . ? N2 C1 1.327(2) . ? N2 C3 1.375(2) . ? N2 C7 1.466(2) . ? N1 C1 1.325(3) . ? N1 C2 1.378(2) . ? N1 C4 1.486(2) . ? C4 C6 1.513(3) . ? C4 C5 1.514(3) . ? C7 C8 1.527(3) . ? C8 C10 1.517(3) . ? C8 C9 1.521(3) . ? C3 C2 1.348(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 N2 C3 108.37(16) . . ? C1 N2 C7 125.40(16) . . ? C3 N2 C7 126.14(15) . . ? C1 N1 C2 108.61(16) . . ? C1 N1 C4 125.40(17) . . ? C2 N1 C4 125.87(17) . . ? N1 C4 C6 110.16(18) . . ? N1 C4 C5 109.16(17) . . ? C6 C4 C5 112.29(19) . . ? N2 C7 C8 113.83(17) . . ? O1 C8 C10 110.67(17) . . ? O1 C8 C9 105.79(17) . . ? C10 C8 C9 111.57(18) . . ? O1 C8 C7 109.65(15) . . ? C10 C8 C7 112.35(17) . . ? C9 C8 C7 106.52(17) . . ? N1 C1 N2 108.83(17) . . ? C2 C3 N2 107.36(17) . . ? C3 C2 N1 106.83(18) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.597 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.069 #===end data_phimbu _database_code_depnum_ccdc_archive 'CCDC 235715' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H23 Cl N2 O' _chemical_formula_weight 294.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.2459(6) _cell_length_b 11.3574(6) _cell_length_c 14.0301(7) _cell_angle_alpha 108.942(2) _cell_angle_beta 91.217(2) _cell_angle_gamma 102.273(2) _cell_volume 1648.29(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8378 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 29.05 _exptl_crystal_description tablet _exptl_crystal_colour colurless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.188 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 15603 _diffrn_reflns_av_R_equivalents 0.0417 _diffrn_reflns_av_sigmaI/netI 0.0429 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 29.07 _reflns_number_total 7953 _reflns_number_gt 6825 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97; PLATON (Spek, 2002)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+0.1256P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geometrically placed, OH from delta-F' _refine_ls_hydrogen_treatment 'riding model, OH as rigid rotor' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7953 _refine_ls_number_parameters 363 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.1124 _refine_ls_wR_factor_gt 0.1086 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1' O 0.50855(8) -0.04174(8) -0.16288(7) 0.0292(2) Uani 1 1 d . . . H1O' H 0.5106 0.0141 -0.1904 0.044 Uiso 1 1 calc R . . N1' N 0.76830(9) 0.02670(9) -0.12735(7) 0.0237(2) Uani 1 1 d . . . C1' C 0.76092(11) 0.14761(11) -0.08601(9) 0.0252(2) Uani 1 1 d . . . H1'A H 0.7190 0.1923 -0.1169 0.030 Uiso 1 1 calc R . . N2' N 0.82202(9) 0.19616(9) 0.00593(8) 0.0248(2) Uani 1 1 d . . . C2' C 0.83561(11) -0.00428(12) -0.05929(9) 0.0267(3) Uani 1 1 d . . . H2'A H 0.8544 -0.0848 -0.0691 0.032 Uiso 1 1 calc R . . C3' C 0.86964(11) 0.10160(12) 0.02389(9) 0.0260(2) Uani 1 1 d . . . H3'A H 0.9172 0.1096 0.0834 0.031 Uiso 1 1 calc R . . C4' C 0.70624(11) -0.05882(11) -0.22606(9) 0.0244(2) Uani 1 1 d . . . H4'A H 0.7550 -0.1219 -0.2576 0.029 Uiso 1 1 calc R . . H4'B H 0.7005 -0.0083 -0.2710 0.029 Uiso 1 1 calc R . . C5' C 0.57657(11) -0.13036(11) -0.21599(9) 0.0237(2) Uani 1 1 d . . . C6' C 0.51395(13) -0.20486(13) -0.32325(10) 0.0330(3) Uani 1 1 d . . . H6'A H 0.4313 -0.2516 -0.3193 0.049 Uiso 1 1 calc R . . H6'B H 0.5614 -0.2656 -0.3596 0.049 Uiso 1 1 calc R . . H6'C H 0.5092 -0.1450 -0.3594 0.049 Uiso 1 1 calc R . . C7' C 0.84115(13) 0.33108(12) 0.07712(10) 0.0326(3) Uani 1 1 d . . . C8' C 0.97888(14) 0.38915(14) 0.09195(12) 0.0424(4) Uani 1 1 d . . . H8'A H 1.0080 0.3906 0.0269 0.064 Uiso 1 1 calc R . . H8'B H 1.0212 0.3373 0.1182 0.064 Uiso 1 1 calc R . . H8'C H 0.9957 0.4767 0.1403 0.064 Uiso 1 1 calc R . . C9' C 0.78994(16) 0.32647(16) 0.17546(11) 0.0454(4) Uani 1 1 d . . . H9'A H 0.8342 0.2792 0.2053 0.068 Uiso 1 1 calc R . . H9'B H 0.7030 0.2834 0.1618 0.068 Uiso 1 1 calc R . . H9'C H 0.7996 0.4138 0.2228 0.068 Uiso 1 1 calc R . . C10' C 0.77416(16) 0.40440(13) 0.02883(13) 0.0458(4) Uani 1 1 d . . . H10D H 0.8088 0.4066 -0.0343 0.069 Uiso 1 1 calc R . . H10E H 0.7836 0.4920 0.0756 0.069 Uiso 1 1 calc R . . H10F H 0.6871 0.3616 0.0142 0.069 Uiso 1 1 calc R . . C51' C 0.58563(11) -0.21796(11) -0.15477(9) 0.0242(2) Uani 1 1 d . . . C52' C 0.63313(14) -0.32520(13) -0.19540(10) 0.0361(3) Uani 1 1 d . . . H52A H 0.6587 -0.3441 -0.2617 0.043 Uiso 1 1 calc R . . C53' C 0.64380(16) -0.40515(14) -0.14059(12) 0.0435(4) Uani 1 1 d . . . H53B H 0.6752 -0.4789 -0.1698 0.052 Uiso 1 1 calc R . . C54' C 0.60867(14) -0.37731(14) -0.04331(11) 0.0370(3) Uani 1 1 d . . . H54B H 0.6147 -0.4325 -0.0059 0.044 Uiso 1 1 calc R . . C55' C 0.56499(13) -0.26937(14) -0.00096(10) 0.0353(3) Uani 1 1 d . . . H55A H 0.5430 -0.2488 0.0665 0.042 Uiso 1 1 calc R . . C56' C 0.55274(12) -0.19000(12) -0.05638(10) 0.0297(3) Uani 1 1 d . . . H56B H 0.5217 -0.1162 -0.0267 0.036 Uiso 1 1 calc R . . O1 O 0.02449(8) 0.03339(9) 0.66130(7) 0.0333(2) Uani 1 1 d . . . H1O H -0.0016 -0.0260 0.6843 0.050 Uiso 1 1 calc R . . N1 N 0.23807(9) -0.19920(9) 0.49639(7) 0.0233(2) Uani 1 1 d . . . C1 C 0.19680(11) -0.15829(11) 0.58668(9) 0.0245(2) Uani 1 1 d . . . H1A H 0.1371 -0.2082 0.6136 0.029 Uiso 1 1 calc R . . N2 N 0.25270(9) -0.03619(9) 0.63309(7) 0.0229(2) Uani 1 1 d . . . C2 C 0.32281(11) -0.09830(11) 0.48437(9) 0.0242(2) Uani 1 1 d . . . H2A H 0.3666 -0.1003 0.4269 0.029 Uiso 1 1 calc R . . C3 C 0.33149(11) 0.00322(11) 0.56935(9) 0.0255(2) Uani 1 1 d . . . H3A H 0.3822 0.0863 0.5829 0.031 Uiso 1 1 calc R . . C4 C 0.22620(11) 0.04156(11) 0.73268(9) 0.0242(2) Uani 1 1 d . . . H4A H 0.3026 0.1019 0.7700 0.029 Uiso 1 1 calc R . . H4B H 0.1951 -0.0149 0.7720 0.029 Uiso 1 1 calc R . . C5 C 0.13055(11) 0.11758(12) 0.72301(9) 0.0256(2) Uani 1 1 d . . . C6 C 0.09744(13) 0.18320(13) 0.82972(10) 0.0346(3) Uani 1 1 d . . . H6A H 0.0361 0.2316 0.8256 0.052 Uiso 1 1 calc R . . H6B H 0.1709 0.2417 0.8715 0.052 Uiso 1 1 calc R . . H6C H 0.0642 0.1183 0.8602 0.052 Uiso 1 1 calc R . . C7 C 0.20518(12) -0.33222(12) 0.42136(10) 0.0311(3) Uani 1 1 d . . . C8 C 0.11142(16) -0.41523(14) 0.46364(13) 0.0501(4) Uani 1 1 d . . . H8A H 0.1476 -0.4189 0.5265 0.075 Uiso 1 1 calc R . . H8B H 0.0865 -0.5018 0.4140 0.075 Uiso 1 1 calc R . . H8C H 0.0398 -0.3783 0.4776 0.075 Uiso 1 1 calc R . . C9 C 0.15161(14) -0.32566(16) 0.32317(11) 0.0443(4) Uani 1 1 d . . . H9A H 0.2130 -0.2716 0.2973 0.066 Uiso 1 1 calc R . . H9B H 0.0796 -0.2892 0.3360 0.066 Uiso 1 1 calc R . . H9C H 0.1278 -0.4120 0.2731 0.066 Uiso 1 1 calc R . . C10 C 0.32216(14) -0.38099(13) 0.40697(11) 0.0371(3) Uani 1 1 d . . . H10A H 0.3541 -0.3841 0.4714 0.056 Uiso 1 1 calc R . . H10B H 0.3832 -0.3232 0.3840 0.056 Uiso 1 1 calc R . . H10C H 0.3044 -0.4670 0.3562 0.056 Uiso 1 1 calc R . . C51 C 0.18400(12) 0.21385(12) 0.67133(9) 0.0268(3) Uani 1 1 d . . . C52 C 0.28522(13) 0.31283(12) 0.71912(10) 0.0317(3) Uani 1 1 d . . . H52B H 0.3163 0.3235 0.7856 0.038 Uiso 1 1 calc R . . C53 C 0.34096(15) 0.39555(14) 0.67109(12) 0.0410(3) Uani 1 1 d . . . H53A H 0.4099 0.4626 0.7046 0.049 Uiso 1 1 calc R . . C54 C 0.29635(17) 0.38074(15) 0.57431(13) 0.0471(4) Uani 1 1 d . . . H54A H 0.3347 0.4375 0.5412 0.057 Uiso 1 1 calc R . . C55 C 0.19602(16) 0.28329(16) 0.52573(12) 0.0457(4) Uani 1 1 d . . . H55B H 0.1653 0.2733 0.4593 0.055 Uiso 1 1 calc R . . C56 C 0.13985(14) 0.19961(14) 0.57407(10) 0.0358(3) Uani 1 1 d . . . H56A H 0.0711 0.1325 0.5403 0.043 Uiso 1 1 calc R . . Cl2 Cl -0.04065(3) -0.20867(3) 0.73218(2) 0.02934(9) Uani 1 1 d . . . Cl1 Cl 0.55600(3) 0.18788(3) -0.24405(2) 0.02770(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1' 0.0286(5) 0.0277(5) 0.0345(5) 0.0107(4) 0.0085(4) 0.0124(4) N1' 0.0218(5) 0.0253(5) 0.0227(5) 0.0074(4) -0.0005(4) 0.0043(4) C1' 0.0230(6) 0.0242(6) 0.0267(6) 0.0082(5) -0.0026(5) 0.0029(5) N2' 0.0228(5) 0.0234(5) 0.0257(5) 0.0068(4) -0.0029(4) 0.0031(4) C2' 0.0242(6) 0.0292(6) 0.0287(6) 0.0107(5) -0.0001(5) 0.0088(5) C3' 0.0232(6) 0.0285(6) 0.0270(6) 0.0103(5) -0.0014(5) 0.0066(5) C4' 0.0246(6) 0.0269(6) 0.0194(5) 0.0047(5) 0.0015(4) 0.0061(5) C5' 0.0233(6) 0.0235(6) 0.0213(6) 0.0032(4) 0.0008(4) 0.0062(4) C6' 0.0342(7) 0.0336(7) 0.0252(6) 0.0056(5) -0.0057(5) 0.0030(6) C7' 0.0344(7) 0.0239(6) 0.0332(7) 0.0020(5) -0.0084(5) 0.0068(5) C8' 0.0377(8) 0.0316(7) 0.0467(9) 0.0069(6) -0.0152(7) -0.0034(6) C9' 0.0497(9) 0.0490(9) 0.0338(8) 0.0016(7) 0.0016(7) 0.0236(7) C10' 0.0522(9) 0.0253(7) 0.0540(10) 0.0058(6) -0.0186(7) 0.0107(6) C51' 0.0235(6) 0.0224(6) 0.0229(6) 0.0041(4) 0.0005(4) 0.0029(4) C52' 0.0543(9) 0.0317(7) 0.0251(6) 0.0075(5) 0.0103(6) 0.0184(6) C53' 0.0655(11) 0.0325(7) 0.0382(8) 0.0112(6) 0.0094(7) 0.0242(7) C54' 0.0414(8) 0.0382(7) 0.0365(8) 0.0190(6) 0.0020(6) 0.0099(6) C55' 0.0372(7) 0.0446(8) 0.0254(6) 0.0130(6) 0.0060(5) 0.0101(6) C56' 0.0305(7) 0.0316(6) 0.0260(6) 0.0062(5) 0.0053(5) 0.0107(5) O1 0.0270(5) 0.0333(5) 0.0356(5) 0.0089(4) -0.0036(4) 0.0033(4) N1 0.0249(5) 0.0199(5) 0.0224(5) 0.0042(4) 0.0055(4) 0.0038(4) C1 0.0267(6) 0.0225(6) 0.0242(6) 0.0071(5) 0.0072(5) 0.0064(5) N2 0.0240(5) 0.0230(5) 0.0209(5) 0.0054(4) 0.0044(4) 0.0072(4) C2 0.0241(6) 0.0240(6) 0.0243(6) 0.0087(5) 0.0054(5) 0.0039(5) C3 0.0257(6) 0.0240(6) 0.0253(6) 0.0075(5) 0.0049(5) 0.0034(5) C4 0.0278(6) 0.0252(6) 0.0182(5) 0.0035(4) 0.0028(4) 0.0088(5) C5 0.0250(6) 0.0262(6) 0.0228(6) 0.0032(5) 0.0016(5) 0.0078(5) C6 0.0379(7) 0.0356(7) 0.0298(7) 0.0058(6) 0.0113(6) 0.0149(6) C7 0.0343(7) 0.0213(6) 0.0288(6) 0.0002(5) 0.0098(5) 0.0000(5) C8 0.0568(10) 0.0239(7) 0.0541(10) 0.0012(6) 0.0269(8) -0.0064(7) C9 0.0352(8) 0.0496(9) 0.0313(7) -0.0027(6) -0.0021(6) 0.0010(7) C10 0.0503(9) 0.0266(6) 0.0359(7) 0.0076(6) 0.0157(6) 0.0156(6) C51 0.0310(6) 0.0259(6) 0.0249(6) 0.0058(5) 0.0041(5) 0.0140(5) C52 0.0352(7) 0.0274(6) 0.0318(7) 0.0066(5) 0.0026(5) 0.0111(5) C53 0.0418(8) 0.0307(7) 0.0516(9) 0.0142(7) 0.0072(7) 0.0095(6) C54 0.0579(10) 0.0429(8) 0.0533(10) 0.0282(8) 0.0160(8) 0.0185(8) C55 0.0602(10) 0.0514(9) 0.0359(8) 0.0219(7) 0.0053(7) 0.0236(8) C56 0.0398(8) 0.0380(7) 0.0307(7) 0.0102(6) -0.0005(6) 0.0142(6) Cl2 0.02651(16) 0.03652(17) 0.02530(16) 0.00989(13) 0.00310(11) 0.00871(12) Cl1 0.02840(16) 0.03522(17) 0.02224(15) 0.01224(12) 0.00345(11) 0.00907(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1' C5' 1.4206(14) . ? N1' C1' 1.3275(15) . ? N1' C2' 1.3818(15) . ? N1' C4' 1.4649(14) . ? C1' N2' 1.3340(15) . ? N2' C3' 1.3849(15) . ? N2' C7' 1.4996(16) . ? C2' C3' 1.3523(17) . ? C4' C5' 1.5447(17) . ? C5' C51' 1.5272(16) . ? C5' C6' 1.5334(17) . ? C7' C9' 1.519(2) . ? C7' C10' 1.5268(19) . ? C7' C8' 1.530(2) . ? C51' C56' 1.3893(17) . ? C51' C52' 1.3901(17) . ? C52' C53' 1.3878(19) . ? C53' C54' 1.384(2) . ? C54' C55' 1.376(2) . ? C55' C56' 1.3925(18) . ? O1 C5 1.4214(15) . ? N1 C1 1.3306(15) . ? N1 C2 1.3849(15) . ? N1 C7 1.4969(15) . ? C1 N2 1.3296(15) . ? N2 C3 1.3820(15) . ? N2 C4 1.4661(14) . ? C2 C3 1.3473(17) . ? C4 C5 1.5445(16) . ? C5 C51 1.5285(17) . ? C5 C6 1.5339(17) . ? C7 C9 1.522(2) . ? C7 C8 1.5231(18) . ? C7 C10 1.525(2) . ? C51 C56 1.3886(18) . ? C51 C52 1.3940(19) . ? C52 C53 1.381(2) . ? C53 C54 1.382(2) . ? C54 C55 1.382(2) . ? C55 C56 1.394(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1' N1' C2' 108.64(10) . . ? C1' N1' C4' 123.96(10) . . ? C2' N1' C4' 127.26(10) . . ? N1' C1' N2' 108.87(10) . . ? C1' N2' C3' 108.33(10) . . ? C1' N2' C7' 126.55(10) . . ? C3' N2' C7' 125.08(10) . . ? C3' C2' N1' 107.12(11) . . ? C2' C3' N2' 107.04(11) . . ? N1' C4' C5' 111.47(9) . . ? O1' C5' C51' 107.45(9) . . ? O1' C5' C6' 109.81(10) . . ? C51' C5' C6' 112.26(10) . . ? O1' C5' C4' 110.22(9) . . ? C51' C5' C4' 109.54(10) . . ? C6' C5' C4' 107.57(10) . . ? N2' C7' C9' 107.91(11) . . ? N2' C7' C10' 108.61(10) . . ? C9' C7' C10' 110.75(13) . . ? N2' C7' C8' 106.87(11) . . ? C9' C7' C8' 112.16(12) . . ? C10' C7' C8' 110.37(12) . . ? C56' C51' C52' 118.41(11) . . ? C56' C51' C5' 121.48(11) . . ? C52' C51' C5' 120.04(11) . . ? C53' C52' C51' 121.03(12) . . ? C54' C53' C52' 119.89(13) . . ? C55' C54' C53' 119.71(12) . . ? C54' C55' C56' 120.42(12) . . ? C51' C56' C55' 120.49(12) . . ? C1 N1 C2 108.27(10) . . ? C1 N1 C7 126.93(10) . . ? C2 N1 C7 124.73(10) . . ? N2 C1 N1 108.90(10) . . ? C1 N2 C3 108.47(10) . . ? C1 N2 C4 123.88(10) . . ? C3 N2 C4 127.55(10) . . ? C3 C2 N1 107.20(10) . . ? C2 C3 N2 107.15(10) . . ? N2 C4 C5 111.46(9) . . ? O1 C5 C51 107.69(10) . . ? O1 C5 C6 110.01(10) . . ? C51 C5 C6 112.15(10) . . ? O1 C5 C4 110.04(10) . . ? C51 C5 C4 109.09(10) . . ? C6 C5 C4 107.85(10) . . ? N1 C7 C9 107.86(11) . . ? N1 C7 C8 108.59(10) . . ? C9 C7 C8 110.59(13) . . ? N1 C7 C10 107.36(11) . . ? C9 C7 C10 111.59(11) . . ? C8 C7 C10 110.71(12) . . ? C56 C51 C52 118.74(13) . . ? C56 C51 C5 121.41(12) . . ? C52 C51 C5 119.66(11) . . ? C53 C52 C51 120.92(13) . . ? C52 C53 C54 119.95(15) . . ? C55 C54 C53 119.99(14) . . ? C54 C55 C56 120.10(14) . . ? C51 C56 C55 120.30(14) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1' H1O' Cl1 0.84 2.30 3.1218(9) 167.4 . O1 H1O Cl2 0.84 2.34 3.1675(10) 168.0 . _diffrn_measured_fraction_theta_max 0.900 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.381 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.048 #===end data_iimaol _database_code_depnum_ccdc_archive 'CCDC 235716' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H15 I N2 O' _chemical_formula_weight 282.12 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P n a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 15.347(3) _cell_length_b 7.6309(14) _cell_length_c 9.725(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1138.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6836 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 27.05 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.645 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 2.776 _exptl_absorpt_correction_type multi-scn _exptl_absorpt_correction_T_min 0.497 _exptl_absorpt_correction_T_max 0.620 #scaled _exptl_absorpt_process_details 'Bruker SADABS v2.03' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 9715 _diffrn_reflns_av_R_equivalents 0.018 _diffrn_reflns_av_sigmaI/netI 0.0155 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 27.60 _reflns_number_total 2611 _reflns_number_gt 2558 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'enCIFer (CCDC, 2003); PLATON (Spek, 2003)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0232P)^2^+0.0997P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geometrically placed, OH and Me from delta-F' _refine_ls_hydrogen_treatment 'riding model, OH and Me as rigid rotors' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.016(14) _refine_ls_number_reflns 2611 _refine_ls_number_parameters 113 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0144 _refine_ls_R_factor_gt 0.0141 _refine_ls_wR_factor_ref 0.0365 _refine_ls_wR_factor_gt 0.0363 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I I 0.593497(5) 0.151201(12) 0.955990(19) 0.02783(4) Uani 1 1 d . . . N1 N 0.45481(10) 0.39291(19) 0.69804(15) 0.0227(3) Uani 1 1 d . . . C1 C 0.42454(12) 0.2303(2) 0.70389(18) 0.0231(3) Uani 1 1 d . . . H1A H 0.4509 0.1302 0.6634 0.028 Uiso 1 1 calc R . . O1 O 0.40382(7) -0.1089(2) 0.91103(16) 0.0288(3) Uani 1 1 d . . . H1B H 0.4446 -0.0358 0.9159 0.043 Uiso 1 1 calc R . . N2 N 0.35070(9) 0.23169(17) 0.77650(16) 0.0213(3) Uani 1 1 d . . . C2 C 0.33462(12) 0.4013(2) 0.81961(19) 0.0251(3) Uani 1 1 d . . . H2A H 0.2865 0.4396 0.8732 0.030 Uiso 1 1 calc R . . C3 C 0.40023(12) 0.5025(3) 0.7712(2) 0.0259(4) Uani 1 1 d . . . H3A H 0.4073 0.6249 0.7848 0.031 Uiso 1 1 calc R . . C4 C 0.53665(13) 0.4452(3) 0.6321(2) 0.0347(4) Uani 1 1 d . . . H4A H 0.5578 0.3494 0.5740 0.052 Uiso 1 1 calc R . . H4B H 0.5802 0.4717 0.7029 0.052 Uiso 1 1 calc R . . H4C H 0.5267 0.5495 0.5755 0.052 Uiso 1 1 calc R . . C5 C 0.29523(13) 0.0789(2) 0.80524(19) 0.0240(3) Uani 1 1 d . . . H5A H 0.2974 -0.0017 0.7255 0.029 Uiso 1 1 calc R . . H5B H 0.2342 0.1188 0.8159 0.029 Uiso 1 1 calc R . . C6 C 0.32245(10) -0.02221(19) 0.9357(2) 0.0239(4) Uani 1 1 d . . . C7 C 0.25470(11) -0.16701(19) 0.9562(4) 0.0351(4) Uani 1 1 d . . . H7A H 0.2726 -0.2427 1.0325 0.053 Uiso 1 1 calc R . . H7B H 0.2500 -0.2368 0.8719 0.053 Uiso 1 1 calc R . . H7C H 0.1980 -0.1142 0.9772 0.053 Uiso 1 1 calc R . . C8 C 0.32798(14) 0.0939(3) 1.06180(19) 0.0304(4) Uani 1 1 d . . . H8A H 0.3741 0.1812 1.0488 0.046 Uiso 1 1 calc R . . H8B H 0.3413 0.0220 1.1426 0.046 Uiso 1 1 calc R . . H8C H 0.2721 0.1536 1.0756 0.046 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I 0.02360(6) 0.03117(7) 0.02873(6) 0.00434(7) 0.00060(8) -0.00256(3) N1 0.0247(8) 0.0213(7) 0.0222(7) 0.0025(5) 0.0017(6) 0.0013(6) C1 0.0250(8) 0.0236(9) 0.0206(8) -0.0008(6) 0.0004(7) 0.0028(7) O1 0.0246(7) 0.0209(6) 0.0408(9) 0.0008(5) 0.0020(5) 0.0022(4) N2 0.0235(7) 0.0183(7) 0.0220(7) 0.0018(5) 0.0004(5) 0.0010(6) C2 0.0281(9) 0.0204(8) 0.0269(9) -0.0012(7) 0.0020(7) 0.0047(7) C3 0.0312(11) 0.0205(8) 0.0259(9) -0.0009(7) 0.0006(7) 0.0028(6) C4 0.0300(10) 0.0316(9) 0.0424(11) 0.0067(8) 0.0101(9) -0.0003(8) C5 0.0247(9) 0.0217(8) 0.0254(9) -0.0011(7) -0.0020(7) -0.0035(7) C6 0.0222(7) 0.0208(7) 0.0286(12) 0.0005(7) 0.0034(7) 0.0007(5) C7 0.0305(8) 0.0287(8) 0.0460(9) 0.0060(12) 0.004(2) -0.0058(6) C8 0.0372(11) 0.0301(9) 0.0239(10) 0.0033(8) 0.0034(8) 0.0031(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.326(2) . ? N1 C3 1.381(2) . ? N1 C4 1.466(2) . ? C1 N2 1.335(2) . ? O1 C6 1.433(2) . ? N2 C2 1.383(2) . ? N2 C5 1.470(2) . ? C2 C3 1.354(3) . ? C5 C6 1.543(3) . ? C6 C8 1.515(3) . ? C6 C7 1.530(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C3 109.40(15) . . ? C1 N1 C4 125.01(15) . . ? C3 N1 C4 125.46(16) . . ? N1 C1 N2 108.23(15) . . ? C1 N2 C2 108.60(14) . . ? C1 N2 C5 125.86(15) . . ? C2 N2 C5 125.53(16) . . ? C3 C2 N2 107.21(16) . . ? C2 C3 N1 106.55(17) . . ? N2 C5 C6 113.34(14) . . ? O1 C6 C8 110.89(16) . . ? O1 C6 C7 106.29(13) . . ? C8 C6 C7 110.8(2) . . ? O1 C6 C5 109.22(16) . . ? C8 C6 C5 112.84(13) . . ? C7 C6 C5 106.52(19) . . ? 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 H1B I 0.84 2.72 3.5503(14) 169.1 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.300 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.051 #===end data_licboe _database_code_depnum_ccdc_archive 'CCDC 235717' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H54 I2 Li4 N4 O4' _chemical_formula_weight 792.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 12.8799(15) _cell_length_b 15.655(2) _cell_length_c 19.034(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.239(2) _cell_angle_gamma 90.00 _cell_volume 3831.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3256 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 24.8 _exptl_crystal_description tablet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 1.674 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.748 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Bruker SADABS v2.03' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 11901 _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4326 _reflns_number_gt 3252 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36a (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ' ?' _computing_publication_material 'enCIFer (CCDC, 2003); PLATON (Spek, 2003)' _refine_special_details ; Disorder in one Et2O molecule modelled over two sites with occupancies 0.45 and 0.55. Suitable distance restraints applied and modelled with isotropic adps. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0540P)^2^+8.4433P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geometrically placed, C4 Me from delta-F' _refine_ls_hydrogen_treatment 'riding model, C4 Me as rigid rotor' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4326 _refine_ls_number_parameters 186 _refine_ls_number_restraints 80 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0975 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 0.922 _refine_ls_restrained_S_all 0.918 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Li1 Li 0.5965(4) 0.0892(4) 0.6872(3) 0.0337(12) Uani 1 1 d U . . Li2 Li 0.4301(4) 0.2051(3) 0.7008(3) 0.0271(11) Uani 1 1 d U . . I1 I 0.390083(19) 0.027022(15) 0.666322(14) 0.04107(10) Uani 1 1 d U . . O2 O 0.57648(15) 0.20809(13) 0.69635(11) 0.0232(4) Uani 1 1 d U . . N1 N 0.8118(2) 0.2317(3) 0.86135(18) 0.0524(10) Uani 1 1 d U . . N2 N 0.7544(2) 0.30110(19) 0.77126(15) 0.0317(6) Uani 1 1 d U . . C1 C 0.7214(3) 0.2541(2) 0.82586(18) 0.0330(8) Uani 1 1 d U . . C2 C 0.8611(3) 0.3076(3) 0.7724(2) 0.0565(13) Uani 1 1 d U . . H2A H 0.9012 0.3366 0.7394 0.068 Uiso 1 1 calc R . . C3 C 0.8966(3) 0.2647(4) 0.8296(3) 0.0784(19) Uani 1 1 d U . . H3A H 0.9674 0.2581 0.8455 0.094 Uiso 1 1 calc R . . C4 C 0.8173(4) 0.1796(4) 0.9250(3) 0.0791(19) Uani 1 1 d U . . H4A H 0.8708 0.1356 0.9212 0.119 Uiso 1 1 calc R . . H4B H 0.7498 0.1524 0.9307 0.119 Uiso 1 1 calc R . . H4C H 0.8350 0.2159 0.9659 0.119 Uiso 1 1 calc R . . C5 C 0.6830(2) 0.3340(2) 0.71514(17) 0.0289(7) Uani 1 1 d U . . H5A H 0.7187 0.3788 0.6888 0.035 Uiso 1 1 calc R . . H5B H 0.6224 0.3607 0.7363 0.035 Uiso 1 1 calc R . . C6 C 0.6450(2) 0.2637(2) 0.66420(16) 0.0243(6) Uani 1 1 d U . . H6A H 0.7073 0.2294 0.6527 0.029 Uiso 1 1 calc R A . C11 C 0.5987(3) 0.3026(2) 0.59355(18) 0.0304(7) Uani 1 1 d U . . C12 C 0.5132(3) 0.3681(3) 0.6053(2) 0.0419(9) Uani 1 1 d U . . H12A H 0.4859 0.3903 0.5598 0.063 Uiso 1 1 calc R A . H12B H 0.5421 0.4152 0.6341 0.063 Uiso 1 1 calc R . . H12C H 0.4569 0.3407 0.6296 0.063 Uiso 1 1 calc R . . C13 C 0.5553(3) 0.2298(3) 0.54719(19) 0.0396(9) Uani 1 1 d U . . H13A H 0.5256 0.2530 0.5027 0.059 Uiso 1 1 calc R A . H13B H 0.5011 0.1996 0.5715 0.059 Uiso 1 1 calc R . . H13C H 0.6115 0.1899 0.5377 0.059 Uiso 1 1 calc R . . C14 C 0.6866(3) 0.3461(3) 0.5547(2) 0.0425(9) Uani 1 1 d U . . H14A H 0.6580 0.3703 0.5103 0.064 Uiso 1 1 calc R A . H14B H 0.7400 0.3037 0.5451 0.064 Uiso 1 1 calc R . . H14C H 0.7176 0.3917 0.5842 0.064 Uiso 1 1 calc R . . C1S C 0.8455(8) 0.0739(8) 0.6958(5) 0.056(3) Uiso 0.45 1 d PDU A 1 H1SA H 0.9164 0.0549 0.7091 0.084 Uiso 0.45 1 calc PR A 1 H1SB H 0.8038 0.0731 0.7373 0.084 Uiso 0.45 1 calc PR A 1 H1SC H 0.8475 0.1322 0.6770 0.084 Uiso 0.45 1 calc PR A 1 C2S C 0.7974(6) 0.0147(5) 0.6402(4) 0.042(2) Uiso 0.45 1 d PDU A 1 H2SA H 0.8396 0.0148 0.5984 0.050 Uiso 0.45 1 calc PR A 1 H2SB H 0.7957 -0.0443 0.6588 0.050 Uiso 0.45 1 calc PR A 1 O1S O 0.6933(4) 0.0430(3) 0.6209(3) 0.0293(12) Uiso 0.45 1 d PDU A 1 C3S C 0.6549(7) 0.0071(5) 0.5551(4) 0.039(2) Uiso 0.45 1 d PDU A 1 H3SA H 0.7079 0.0142 0.5199 0.047 Uiso 0.45 1 calc PR A 1 H3SB H 0.5917 0.0384 0.5380 0.047 Uiso 0.45 1 calc PR A 1 C4S C 0.6295(7) -0.0857(5) 0.5618(5) 0.051(2) Uiso 0.45 1 d PDU A 1 H4SA H 0.6036 -0.1079 0.5160 0.076 Uiso 0.45 1 calc PR A 1 H4SB H 0.5761 -0.0929 0.5960 0.076 Uiso 0.45 1 calc PR A 1 H4SC H 0.6923 -0.1171 0.5778 0.076 Uiso 0.45 1 calc PR A 1 C1SA C 0.9002(5) 0.1022(5) 0.6504(4) 0.054(2) Uiso 0.55 1 d PDU A 2 H1SD H 0.9616 0.1088 0.6827 0.082 Uiso 0.55 1 calc PR A 2 H1SE H 0.8766 0.1585 0.6337 0.082 Uiso 0.55 1 calc PR A 2 H1SF H 0.9180 0.0671 0.6101 0.082 Uiso 0.55 1 calc PR A 2 C2SA C 0.8156(6) 0.0598(7) 0.6877(4) 0.056(2) Uiso 0.55 1 d PDU A 2 H2SC H 0.8403 0.0033 0.7049 0.067 Uiso 0.55 1 calc PR A 2 H2SD H 0.7995 0.0946 0.7291 0.067 Uiso 0.55 1 calc PR A 2 O1SA O 0.7227(3) 0.0486(3) 0.6439(3) 0.0370(12) Uiso 0.55 1 d PDU A 2 C3SA C 0.7320(5) -0.0188(5) 0.5935(4) 0.0500(19) Uiso 0.55 1 d PDU A 2 H3SC H 0.7479 -0.0732 0.6183 0.060 Uiso 0.55 1 calc PR A 2 H3SD H 0.7898 -0.0059 0.5630 0.060 Uiso 0.55 1 calc PR A 2 C4SA C 0.6320(7) -0.0277(7) 0.5490(4) 0.062(2) Uiso 0.55 1 d PDU A 2 H4SD H 0.6391 -0.0737 0.5147 0.093 Uiso 0.55 1 calc PR A 2 H4SE H 0.6168 0.0261 0.5242 0.093 Uiso 0.55 1 calc PR A 2 H4SF H 0.5752 -0.0412 0.5793 0.093 Uiso 0.55 1 calc PR A 2 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 Li1 0.034(3) 0.026(3) 0.041(3) -0.002(2) 0.008(2) 0.001(2) Li2 0.025(2) 0.029(3) 0.028(3) 0.001(2) 0.000(2) 0.001(2) I1 0.04341(16) 0.03124(14) 0.04919(17) -0.01090(11) 0.00824(11) -0.01416(10) O2 0.0203(10) 0.0218(11) 0.0279(12) 0.0008(9) 0.0041(9) -0.0016(8) N1 0.0288(16) 0.084(3) 0.043(2) 0.0244(18) -0.0087(14) -0.0146(17) N2 0.0236(13) 0.0384(16) 0.0328(16) -0.0004(12) -0.0013(11) -0.0091(12) C1 0.0290(17) 0.0371(19) 0.0324(19) 0.0006(15) -0.0014(14) -0.0058(14) C2 0.0215(17) 0.092(4) 0.055(3) 0.023(2) -0.0007(17) -0.016(2) C3 0.024(2) 0.139(5) 0.070(3) 0.044(3) -0.012(2) -0.018(3) C4 0.052(3) 0.122(5) 0.060(3) 0.048(3) -0.023(2) -0.024(3) C5 0.0289(16) 0.0274(17) 0.0303(18) 0.0012(13) 0.0018(13) -0.0020(13) C6 0.0194(14) 0.0233(16) 0.0307(17) -0.0008(13) 0.0051(12) 0.0001(12) C11 0.0302(17) 0.0317(18) 0.0294(18) 0.0034(14) 0.0016(14) -0.0031(14) C12 0.040(2) 0.041(2) 0.044(2) 0.0120(17) -0.0011(17) 0.0089(17) C13 0.045(2) 0.045(2) 0.0278(19) -0.0015(16) -0.0030(16) -0.0097(17) C14 0.051(2) 0.046(2) 0.032(2) 0.0079(17) 0.0078(17) -0.0148(18) _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 Li1 O2 1.888(6) . ? Li1 O1S 1.963(8) . ? Li1 O1SA 1.970(7) . ? Li1 Li2 2.831(8) . ? Li1 Li2 2.835(8) 2_656 ? Li1 I1 2.838(6) . ? Li1 I1 2.948(6) 2_656 ? Li2 O2 1.893(5) . ? Li2 O2 1.965(6) 2_656 ? Li2 C1 2.131(6) 2_656 ? Li2 Li2 2.524(10) 2_656 ? Li2 Li1 2.835(8) 2_656 ? Li2 I1 2.904(5) . ? I1 Li1 2.948(6) 2_656 ? O2 C6 1.404(4) . ? O2 Li2 1.965(6) 2_656 ? N1 C1 1.358(4) . ? N1 C3 1.379(5) . ? N1 C4 1.459(5) . ? N2 C1 1.361(4) . ? N2 C2 1.378(4) . ? N2 C5 1.463(4) . ? C1 Li2 2.131(6) 2_656 ? C2 C3 1.338(6) . ? C5 C6 1.530(4) . ? C6 C11 1.564(5) . ? C11 C13 1.529(5) . ? C11 C12 1.529(5) . ? C11 C14 1.545(5) . ? C1S C2S 1.512(8) . ? C2S O1S 1.440(7) . ? O1S C3S 1.435(7) . ? C3S C4S 1.497(8) . ? C1SA C2SA 1.489(8) . ? C2SA O1SA 1.429(7) . ? O1SA C3SA 1.436(6) . ? C3SA C4SA 1.506(8) . ? 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 O2 Li1 O1S 121.1(3) . . ? O2 Li1 O1SA 118.4(3) . . ? O1S Li1 O1SA 16.66(17) . . ? O2 Li1 Li2 41.58(17) . . ? O1S Li1 Li2 143.8(3) . . ? O1SA Li1 Li2 153.1(3) . . ? O2 Li1 Li2 43.70(18) . 2_656 ? O1S Li1 Li2 145.9(3) . 2_656 ? O1SA Li1 Li2 131.2(3) . 2_656 ? Li2 Li1 Li2 52.9(2) . 2_656 ? O2 Li1 I1 102.7(2) . . ? O1S Li1 I1 114.1(3) . . ? O1SA Li1 I1 128.3(3) . . ? Li2 Li1 I1 61.63(16) . . ? Li2 Li1 I1 100.0(2) 2_656 . ? O2 Li1 I1 103.9(2) . 2_656 ? O1S Li1 I1 118.8(3) . 2_656 ? O1SA Li1 I1 106.5(3) . 2_656 ? Li2 Li1 I1 97.5(2) . 2_656 ? Li2 Li1 I1 60.24(16) 2_656 2_656 ? I1 Li1 I1 91.38(16) . 2_656 ? O2 Li2 O2 98.2(2) . 2_656 ? O2 Li2 C1 151.9(3) . 2_656 ? O2 Li2 C1 97.9(2) 2_656 2_656 ? O2 Li2 Li2 50.39(19) . 2_656 ? O2 Li2 Li2 47.90(19) 2_656 2_656 ? C1 Li2 Li2 141.4(3) 2_656 2_656 ? O2 Li2 Li1 41.46(17) . . ? O2 Li2 Li1 100.4(2) 2_656 . ? C1 Li2 Li1 153.7(3) 2_656 . ? Li2 Li2 Li1 63.6(2) 2_656 . ? O2 Li2 Li1 102.2(2) . 2_656 ? O2 Li2 Li1 41.60(17) 2_656 2_656 ? C1 Li2 Li1 105.2(2) 2_656 2_656 ? Li2 Li2 Li1 63.5(2) 2_656 2_656 ? Li1 Li2 Li1 77.4(3) . 2_656 ? O2 Li2 I1 100.3(2) . . ? O2 Li2 I1 103.3(2) 2_656 . ? C1 Li2 I1 98.2(2) 2_656 . ? Li2 Li2 I1 106.12(10) 2_656 . ? Li1 Li2 I1 59.30(16) . . ? Li1 Li2 I1 61.81(16) 2_656 . ? Li1 I1 Li2 59.07(15) . . ? Li1 I1 Li1 75.49(19) . 2_656 ? Li2 I1 Li1 57.94(15) . 2_656 ? C6 O2 Li1 118.6(2) . . ? C6 O2 Li2 133.4(2) . . ? Li1 O2 Li2 97.0(3) . . ? C6 O2 Li2 120.8(2) . 2_656 ? Li1 O2 Li2 94.7(3) . 2_656 ? Li2 O2 Li2 81.7(2) . 2_656 ? C1 N1 C3 111.3(3) . . ? C1 N1 C4 123.9(3) . . ? C3 N1 C4 124.8(3) . . ? C1 N2 C2 112.5(3) . . ? C1 N2 C5 122.5(3) . . ? C2 N2 C5 124.8(3) . . ? N1 C1 N2 102.9(3) . . ? N1 C1 Li2 140.6(3) . 2_656 ? N2 C1 Li2 109.5(3) . 2_656 ? C3 C2 N2 105.7(4) . . ? C2 C3 N1 107.6(3) . . ? N2 C5 C6 112.0(3) . . ? O2 C6 C5 110.9(2) . . ? O2 C6 C11 113.5(2) . . ? C5 C6 C11 110.9(3) . . ? C13 C11 C12 110.0(3) . . ? C13 C11 C14 107.8(3) . . ? C12 C11 C14 109.2(3) . . ? C13 C11 C6 108.3(3) . . ? C12 C11 C6 112.2(3) . . ? C14 C11 C6 109.2(3) . . ? O1S C2S C1S 109.2(6) . . ? C3S O1S C2S 111.9(5) . . ? C3S O1S Li1 120.4(5) . . ? C2S O1S Li1 124.4(5) . . ? O1S C3S C4S 111.8(6) . . ? O1SA C2SA C1SA 112.8(6) . . ? C2SA O1SA C3SA 112.4(6) . . ? C2SA O1SA Li1 113.6(5) . . ? C3SA O1SA Li1 128.2(4) . . ? O1SA C3SA C4SA 110.0(6) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.896 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.087 #===end data_CUIMSM _database_code_depnum_ccdc_archive 'CCDC 235718' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C46 H62 Cl4 Cu4 N8 O3, 0.6(C4 H6 O)' _chemical_formula_sum 'C48.4 H65.6 Cl4 Cu4 N8 O3.6' _chemical_formula_weight 1215.46 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 41 21 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+1/4' 'y+1/2, -x+1/2, z+3/4' '-x+1/2, y+1/2, -z+1/4' 'x+1/2, -y+1/2, -z+3/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 14.763(3) _cell_length_b 14.763 _cell_length_c 27.053(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5896(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2878 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 27.4 _exptl_crystal_description tablet _exptl_crystal_colour 'dark orange' _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2509 _exptl_absorpt_coefficient_mu 1.649 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.45 _exptl_absorpt_correction_T_max 1.10 _exptl_absorpt_process_details 'Bruker SADABS v2.03 (Bruker, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 36171 _diffrn_reflns_av_R_equivalents 0.189 _diffrn_reflns_av_sigmaI/netI 0.127 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7023 _reflns_number_gt 2662 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART v5.624' _computing_cell_refinement 'Bruker SMART v5.624' _computing_data_reduction 'Bruker SAINT v6.02a' _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.083P)^2^+16.895P] 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 No _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.35(5) _refine_ls_number_reflns 5208 _refine_ls_number_parameters 310 _refine_ls_number_restraints 40 _refine_ls_R_factor_all 0.165 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.214 _refine_ls_wR_factor_gt 0.147 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.162 _refine_ls_shift/su_mean 0.014 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.73265(10) 0.86075(11) 0.96452(5) 0.0530(4) Uani 1 1 d . . . Cu2 Cu 0.93420(10) 0.86417(11) 0.94844(5) 0.0567(5) Uani 1 1 d . . . Cl1 Cl 0.6445(2) 0.8259(2) 1.03235(10) 0.0550(8) Uani 1 1 d . . . Cl2 Cl 1.0497(2) 0.8342(2) 1.00326(10) 0.0583(8) Uani 1 1 d . . . O1 O 0.8219(5) 0.8676(6) 0.9101(2) 0.057(2) Uani 1 1 d . A . O2 O 0.8475(5) 0.8475(5) 1.0000 0.049(3) Uani 1 2 d S . . N1 N 0.9706(9) 0.8194(10) 0.8490(3) 0.079(4) Uani 1 1 d . . . N2 N 1.0718(9) 0.9193(10) 0.8667(5) 0.080(4) Uani 1 1 d . . . N3 N 0.6454(7) 0.8271(7) 0.8721(3) 0.060(3) Uani 1 1 d . . . N4 N 0.5593(8) 0.9281(8) 0.9054(4) 0.061(3) Uani 1 1 d . . . C1 C 0.8014(12) 0.9213(15) 0.8258(6) 0.047(7) Uiso 0.56(2) 1 d PD A 1 C2 C 0.7971(13) 0.9073(15) 0.7745(7) 0.069(8) Uiso 0.56(2) 1 d PD A 1 H2A H 0.8079 0.8487 0.7612 0.082 Uiso 0.56(2) 1 calc PR A 1 C3 C 0.7766(13) 0.9803(17) 0.7428(7) 0.070(7) Uiso 0.56(2) 1 d PD A 1 H3A H 0.7737 0.9710 0.7081 0.084 Uiso 0.56(2) 1 calc PR A 1 C4 C 0.7613(14) 1.0632(16) 0.7617(7) 0.077(9) Uiso 0.56(2) 1 d PD A 1 H4A H 0.7477 1.1117 0.7399 0.093 Uiso 0.56(2) 1 calc PR A 1 C5 C 0.7647(15) 1.0797(14) 0.8108(9) 0.097(11) Uiso 0.56(2) 1 d PD A 1 H5A H 0.7535 1.1390 0.8230 0.117 Uiso 0.56(2) 1 calc PR A 1 C6 C 0.7850(13) 1.0086(15) 0.8439(7) 0.070(7) Uiso 0.56(2) 1 d PD A 1 H6A H 0.7875 1.0199 0.8784 0.084 Uiso 0.56(2) 1 calc PR A 1 C1' C 0.8001(14) 0.8889(15) 0.8221(6) 0.039(8) Uiso 0.44(2) 1 d PD A 2 C2' C 0.7820(15) 0.8681(16) 0.7724(8) 0.065(9) Uiso 0.44(2) 1 d PD A 2 H2'A H 0.7647 0.8084 0.7634 0.078 Uiso 0.44(2) 1 calc PR A 2 C3' C 0.7896(15) 0.9357(19) 0.7358(7) 0.055(9) Uiso 0.44(2) 1 d PD A 2 H3'A H 0.7773 0.9217 0.7021 0.066 Uiso 0.44(2) 1 calc PR A 2 C4' C 0.8143(16) 1.0205(17) 0.7487(9) 0.076(11) Uiso 0.44(2) 1 d PD A 2 H4'A H 0.8192 1.0654 0.7237 0.091 Uiso 0.44(2) 1 calc PR A 2 C5' C 0.8323(17) 1.0438(15) 0.7960(9) 0.082(11) Uiso 0.44(2) 1 d PD A 2 H5'A H 0.8494 1.1041 0.8038 0.098 Uiso 0.44(2) 1 calc PR A 2 C6' C 0.8255(15) 0.9780(16) 0.8338(8) 0.050(8) Uiso 0.44(2) 1 d PD A 2 H6'A H 0.8382 0.9941 0.8671 0.060 Uiso 0.44(2) 1 calc PR A 2 C10 C 0.8097(9) 0.8317(10) 0.8617(4) 0.061(4) Uani 1 1 d . . . C11 C 0.8886(10) 0.7687(12) 0.8505(4) 0.080(5) Uani 1 1 d . A . H11A H 0.8927 0.7214 0.8763 0.096 Uiso 1 1 calc R . . H11B H 0.8787 0.7385 0.8182 0.096 Uiso 1 1 calc R . . C12 C 1.0001(10) 0.8778(13) 0.8855(5) 0.080(5) Uani 1 1 d . . . C13 C 1.0286(11) 0.8218(14) 0.8087(5) 0.087(6) Uani 1 1 d . . . H13A H 1.0268 0.7855 0.7797 0.104 Uiso 1 1 calc R . . C14 C 1.0865(12) 0.8857(16) 0.8198(5) 0.106(7) Uani 1 1 d . . . H14A H 1.1330 0.9063 0.7983 0.127 Uiso 1 1 calc R . . C15 C 1.1233(13) 0.9936(13) 0.8896(7) 0.096(6) Uani 1 1 d . . . C16 C 1.2031(13) 0.9634(12) 0.9200(7) 0.112(6) Uani 1 1 d . . . H16A H 1.2454 0.9295 0.8991 0.169 Uiso 1 1 calc R . . H16B H 1.1821 0.9244 0.9470 0.169 Uiso 1 1 calc R . . H16C H 1.2338 1.0165 0.9338 0.169 Uiso 1 1 calc R . . C17 C 1.0610(14) 1.0453(13) 0.9257(9) 0.146(9) Uani 1 1 d . . . H17A H 1.0398 1.0038 0.9515 0.219 Uiso 1 1 calc R . . H17B H 1.0089 1.0696 0.9076 0.219 Uiso 1 1 calc R . . H17C H 1.0948 1.0951 0.9409 0.219 Uiso 1 1 calc R . . C18 C 1.1551(16) 1.0599(15) 0.8497(8) 0.163(10) Uani 1 1 d . . . H18A H 1.1947 1.0283 0.8263 0.244 Uiso 1 1 calc R . . H18B H 1.1885 1.1097 0.8652 0.244 Uiso 1 1 calc R . . H18C H 1.1024 1.0841 0.8321 0.244 Uiso 1 1 calc R . . C21 C 0.7243(9) 0.7734(10) 0.8609(4) 0.060(4) Uani 1 1 d . A . H21A H 0.7172 0.7455 0.8279 0.072 Uiso 1 1 calc R . . H21B H 0.7301 0.7240 0.8855 0.072 Uiso 1 1 calc R . . C22 C 0.6375(9) 0.8820(9) 0.9128(4) 0.057(3) Uani 1 1 d . . . C23 C 0.5782(10) 0.8446(11) 0.8394(5) 0.072(4) Uani 1 1 d . . . H23A H 0.5712 0.8181 0.8076 0.086 Uiso 1 1 calc R . . C24 C 0.5235(11) 0.9065(12) 0.8602(6) 0.079(4) Uani 1 1 d . . . H24A H 0.4698 0.9309 0.8462 0.095 Uiso 1 1 calc R . . C25 C 0.5172(11) 0.9951(12) 0.9398(6) 0.081(5) Uani 1 1 d . . . C26 C 0.4541(10) 0.9505(12) 0.9742(5) 0.092(5) Uani 1 1 d . . . H26A H 0.4866 0.9044 0.9933 0.137 Uiso 1 1 calc R . . H26B H 0.4051 0.9217 0.9555 0.137 Uiso 1 1 calc R . . H26C H 0.4285 0.9956 0.9968 0.137 Uiso 1 1 calc R . . C27 C 0.4685(12) 1.0674(14) 0.9096(6) 0.109(6) Uani 1 1 d . . . H27A H 0.4194 1.0392 0.8906 0.163 Uiso 1 1 calc R . . H27B H 0.5115 1.0960 0.8868 0.163 Uiso 1 1 calc R . . H27C H 0.4432 1.1133 0.9318 0.163 Uiso 1 1 calc R . . C28 C 0.5921(10) 1.0412(10) 0.9685(6) 0.086(5) Uani 1 1 d . . . H28A H 0.6247 0.9962 0.9883 0.129 Uiso 1 1 calc R . . H28B H 0.5660 1.0873 0.9904 0.129 Uiso 1 1 calc R . . H28C H 0.6343 1.0702 0.9454 0.129 Uiso 1 1 calc R . . C1S C 0.869(3) 1.256(3) 0.9192(15) 0.067(12) Uiso 0.30 1 d PD . . H1SA H 0.8767 1.2353 0.9532 0.100 Uiso 0.30 1 calc PR . . H1SB H 0.8654 1.3228 0.9189 0.100 Uiso 0.30 1 calc PR . . H1SC H 0.9204 1.2367 0.8991 0.100 Uiso 0.30 1 calc PR . . C2S C 0.784(4) 1.218(4) 0.8986(17) 0.096(17) Uiso 0.30 1 d PD . . H2SA H 0.7888 1.1516 0.9003 0.115 Uiso 0.30 1 calc PR . . H2SB H 0.7339 1.2368 0.9205 0.115 Uiso 0.30 1 calc PR . . O3S O 0.761(2) 1.242(2) 0.8501(11) 0.076(9) Uiso 0.30 1 d PD . . C4S C 0.679(3) 1.206(3) 0.8337(16) 0.082(15) Uiso 0.30 1 d PD . . H4SB H 0.6291 1.2305 0.8545 0.098 Uiso 0.30 1 calc PR . . H4SC H 0.6796 1.1395 0.8384 0.098 Uiso 0.30 1 calc PR . . C5S C 0.658(4) 1.226(4) 0.7814(17) 0.102(18) Uiso 0.30 1 d PD . . H5SC H 0.5995 1.1993 0.7725 0.153 Uiso 0.30 1 calc PR . . H5SD H 0.7056 1.2000 0.7603 0.153 Uiso 0.30 1 calc PR . . H5SA H 0.6558 1.2916 0.7765 0.153 Uiso 0.30 1 calc PR . . 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 Cu1 0.0598(10) 0.0671(11) 0.0321(7) -0.0004(7) 0.0005(7) 0.0005(8) Cu2 0.0591(10) 0.0751(12) 0.0358(7) 0.0045(8) 0.0012(7) 0.0045(9) Cl1 0.0647(19) 0.0606(18) 0.0396(15) 0.0029(14) 0.0046(14) 0.0010(17) Cl2 0.062(2) 0.066(2) 0.0462(16) 0.0017(15) -0.0068(15) 0.0017(17) O1 0.068(5) 0.080(6) 0.023(4) 0.009(4) 0.003(4) 0.004(5) O2 0.053(4) 0.053(4) 0.042(6) -0.001(3) 0.001(3) 0.015(6) N1 0.082(9) 0.135(12) 0.020(5) 0.000(6) -0.001(6) 0.002(8) N2 0.065(8) 0.098(11) 0.076(9) 0.029(8) 0.006(7) 0.018(8) N3 0.057(7) 0.083(8) 0.039(6) -0.008(5) 0.001(5) 0.003(7) N4 0.064(7) 0.077(8) 0.042(6) -0.010(6) -0.010(5) 0.005(7) C10 0.068(9) 0.094(10) 0.021(6) -0.006(6) -0.012(6) 0.014(9) C11 0.064(10) 0.138(15) 0.036(7) -0.034(8) -0.003(6) 0.019(10) C12 0.050(9) 0.119(14) 0.072(10) 0.038(10) -0.007(7) 0.002(9) C13 0.072(11) 0.141(17) 0.048(9) 0.000(9) -0.003(8) 0.037(11) C14 0.078(12) 0.20(2) 0.036(8) 0.038(11) 0.015(8) 0.022(14) C15 0.090(14) 0.081(12) 0.115(14) 0.047(11) 0.024(12) 0.000(11) C16 0.091(14) 0.108(15) 0.139(16) 0.008(12) -0.041(12) -0.011(12) C17 0.087(14) 0.096(15) 0.26(3) -0.018(17) 0.034(17) -0.017(12) C18 0.128(19) 0.17(2) 0.20(2) 0.089(18) 0.023(17) -0.033(18) C21 0.068(9) 0.082(10) 0.030(6) -0.010(6) -0.017(6) 0.016(9) C22 0.056(9) 0.070(9) 0.045(7) 0.005(6) 0.004(6) -0.009(8) C23 0.072(10) 0.096(12) 0.047(8) 0.010(8) -0.016(7) -0.014(10) C24 0.067(10) 0.098(13) 0.073(10) 0.009(9) -0.009(8) 0.007(10) C25 0.062(10) 0.096(12) 0.085(11) 0.004(10) -0.005(9) -0.010(9) C26 0.075(11) 0.127(15) 0.073(10) -0.007(10) 0.026(9) -0.010(10) C27 0.084(13) 0.135(17) 0.107(13) 0.000(13) -0.043(10) 0.028(12) C28 0.075(11) 0.088(11) 0.095(11) -0.016(9) 0.002(9) 0.014(9) _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 Cu1 O2 1.958(6) . ? Cu1 O1 1.979(7) . ? Cu1 C22 2.008(13) . ? Cu1 Cl1 2.308(3) . ? Cu1 Cu2 3.008(2) . ? Cu2 O2 1.909(6) . ? Cu2 O1 1.956(8) . ? Cu2 C12 1.971(15) . ? Cu2 Cl2 2.303(3) . ? O1 C10 1.425(13) . ? O2 Cu2 1.909(6) 7_557 ? O2 Cu1 1.959(6) 7_557 ? N1 C12 1.38(2) . ? N1 C13 1.388(18) . ? N1 C11 1.424(19) . ? N2 C12 1.324(18) . ? N2 C14 1.38(2) . ? N2 C15 1.47(2) . ? N3 C23 1.355(15) . ? N3 C22 1.371(14) . ? N3 C21 1.441(15) . ? N4 C22 1.356(16) . ? N4 C24 1.369(17) . ? N4 C25 1.494(19) . ? C1 C6 1.400(15) . ? C1 C2 1.402(14) . ? C1 C10 1.65(2) . ? C2 C3 1.411(18) . ? C3 C4 1.346(18) . ? C4 C5 1.350(18) . ? C5 C6 1.413(18) . ? C1' C2' 1.404(14) . ? C1' C6' 1.404(15) . ? C1' C10 1.37(2) . ? C2' C3' 1.411(18) . ? C3' C4' 1.350(18) . ? C4' C5' 1.351(18) . ? C5' C6' 1.413(18) . ? C10 C11 1.521(19) . ? C10 C21 1.527(18) . ? C13 C14 1.31(2) . ? C15 C16 1.51(2) . ? C15 C18 1.53(2) . ? C15 C17 1.54(2) . ? C23 C24 1.34(2) . ? C25 C26 1.47(2) . ? C25 C28 1.51(2) . ? C25 C27 1.52(2) . ? C1S C2S 1.48(5) . ? C2S O3S 1.40(4) . ? O3S C4S 1.40(4) . ? C4S C5S 1.48(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 O2 Cu1 O1 78.1(3) . . ? O2 Cu1 C22 164.4(4) . . ? O1 Cu1 C22 86.5(4) . . ? O2 Cu1 Cl1 94.39(19) . . ? O1 Cu1 Cl1 168.2(3) . . ? C22 Cu1 Cl1 101.2(4) . . ? O2 Cu1 Cu2 38.36(15) . . ? O1 Cu1 Cu2 39.9(2) . . ? C22 Cu1 Cu2 126.1(3) . . ? Cl1 Cu1 Cu2 132.59(10) . . ? O2 Cu2 O1 79.8(3) . . ? O2 Cu2 C12 167.2(5) . . ? O1 Cu2 C12 87.6(5) . . ? O2 Cu2 Cl2 90.07(16) . . ? O1 Cu2 Cl2 166.9(3) . . ? C12 Cu2 Cl2 102.1(4) . . ? O2 Cu2 Cu1 39.55(15) . . ? O1 Cu2 Cu1 40.4(2) . . ? C12 Cu2 Cu1 128.0(4) . . ? Cl2 Cu2 Cu1 129.52(10) . . ? C10 O1 Cu2 125.8(7) . . ? C10 O1 Cu1 125.5(8) . . ? Cu2 O1 Cu1 99.7(3) . . ? Cu2 O2 Cu2 111.2(5) 7_557 . ? Cu2 O2 Cu1 113.76(7) 7_557 . ? Cu2 O2 Cu1 102.10(6) . . ? Cu2 O2 Cu1 102.10(6) 7_557 7_557 ? Cu2 O2 Cu1 113.75(7) . 7_557 ? Cu1 O2 Cu1 114.4(5) . 7_557 ? C12 N1 C13 110.6(14) . . ? C12 N1 C11 125.2(11) . . ? C13 N1 C11 124.0(13) . . ? C12 N2 C14 108.3(16) . . ? C12 N2 C15 126.6(14) . . ? C14 N2 C15 125.0(16) . . ? C23 N3 C22 110.5(12) . . ? C23 N3 C21 123.9(11) . . ? C22 N3 C21 124.3(11) . . ? C22 N4 C24 110.1(12) . . ? C22 N4 C25 126.5(11) . . ? C24 N4 C25 123.4(13) . . ? C6 C1 C2 118.3(18) . . ? C6 C1 C10 123.1(13) . . ? C2 C1 C10 117.9(16) . . ? C3 C2 C1 119.9(16) . . ? C4 C3 C2 119.9(17) . . ? C3 C4 C5 122(2) . . ? C4 C5 C6 119.8(17) . . ? C5 C6 C1 119.9(15) . . ? C2' C1' C6' 118.1(18) . . ? C2' C1' C10 129.2(19) . . ? C6' C1' C10 111.9(15) . . ? C1' C2' C3' 120.2(16) . . ? C4' C3' C2' 119.6(17) . . ? C3' C4' C5' 122(2) . . ? C4' C5' C6' 119.8(18) . . ? C1' C6' C5' 120.0(16) . . ? O1 C10 C1' 120.1(14) . . ? O1 C10 C1 104.6(12) . . ? C1' C10 C1 15.5(10) . . ? O1 C10 C11 108.3(9) . . ? C1' C10 C11 107.4(13) . . ? C1 C10 C11 115.5(12) . . ? O1 C10 C21 109.1(9) . . ? C1' C10 C21 104.6(12) . . ? C1 C10 C21 112.6(11) . . ? C11 C10 C21 106.6(12) . . ? N1 C11 C10 109.6(14) . . ? N2 C12 N1 105.4(14) . . ? N2 C12 Cu2 140.7(13) . . ? N1 C12 Cu2 113.4(11) . . ? C14 C13 N1 104.0(15) . . ? C13 C14 N2 111.6(15) . . ? N2 C15 C16 114.5(14) . . ? N2 C15 C18 109.8(17) . . ? C16 C15 C18 109.6(17) . . ? N2 C15 C17 109.1(15) . . ? C16 C15 C17 105.5(17) . . ? C18 C15 C17 108.2(17) . . ? N3 C21 C10 110.7(11) . . ? N4 C22 N3 104.5(11) . . ? N4 C22 Cu1 141.0(9) . . ? N3 C22 Cu1 114.1(10) . . ? C24 C23 N3 107.2(13) . . ? C23 C24 N4 107.5(13) . . ? C26 C25 N4 111.1(14) . . ? C26 C25 C28 109.9(14) . . ? N4 C25 C28 108.3(12) . . ? C26 C25 C27 110.7(14) . . ? N4 C25 C27 108.9(13) . . ? C28 C25 C27 107.8(14) . . ? O3S C2S C1S 118(4) . . ? C4S O3S C2S 115(4) . . ? O3S C4S C5S 114(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.49 _refine_diff_density_min -0.48 _refine_diff_density_rms 0.10 #===end