# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof Rita Delgado' _publ_contact_author_email DELGADO@ITQB.UNL.PT _publ_section_title ; Cyclam derivatives containing three acetate pendant arms: synthesis, acid-base, metal complexation and structural studies ; loop_ _publ_author_name 'Rita Delgado' 'Paula Brandao' 'Michael Drew' 'Vitor Felix' 'Luis M. P. Lima' # Attachment 'B809100E.cif' data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 689800' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H38 I N7 O4' _chemical_formula_weight 531.44 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.0163(4) _cell_length_b 8.6813(2) _cell_length_c 16.8648(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.7190(10) _cell_angle_gamma 90.00 _cell_volume 2336.97(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block shaped' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 1.406 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.872 _exptl_absorpt_correction_T_max 0.934 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 87430 _diffrn_reflns_av_R_equivalents 0.0414 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 33.11 _reflns_number_total 8768 _reflns_number_gt 7052 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0137P)^2^+2.0233P] 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 8768 _refine_ls_number_parameters 299 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0526 _refine_ls_wR_factor_gt 0.0470 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I I 0.504327(6) 0.510205(11) 0.175698(6) 0.01528(3) Uani 1 d . . . N1 N 0.21719(7) 1.28911(14) -0.10730(7) 0.0117(2) Uani 1 d . . . C2 C 0.25278(10) 1.19344(17) -0.16834(9) 0.0143(3) Uani 1 d . . . H2A H 0.3145 1.1909 -0.1582 0.017 Uiso 1 calc R . . H2B H 0.2391 1.2403 -0.2213 0.017 Uiso 1 calc R . . C3 C 0.21907(9) 1.03016(17) -0.16852(9) 0.0137(3) Uani 1 d . . . H3A H 0.1571 1.0330 -0.1720 0.016 Uiso 1 calc R . . H3B H 0.2363 0.9748 -0.2158 0.016 Uiso 1 calc R . . N4 N 0.25021(8) 0.94711(14) -0.09625(7) 0.0113(2) Uani 1 d . . . C5 C 0.19535(9) 0.81854(17) -0.07793(9) 0.0140(3) Uani 1 d . . . H5A H 0.2242 0.7548 -0.0354 0.017 Uiso 1 calc R . . H5B H 0.1853 0.7531 -0.1258 0.017 Uiso 1 calc R . . C6 C 0.11073(9) 0.87166(17) -0.05101(9) 0.0147(3) Uani 1 d . . . H6A H 0.1092 0.9856 -0.0501 0.018 Uiso 1 calc R . . H6B H 0.0653 0.8359 -0.0900 0.018 Uiso 1 calc R . . C7 C 0.09516(9) 0.81030(18) 0.03131(9) 0.0155(3) Uani 1 d . . . H7A H 0.0360 0.8294 0.0414 0.019 Uiso 1 calc R . . H7B H 0.1045 0.6976 0.0325 0.019 Uiso 1 calc R . . N8 N 0.15023(8) 0.88305(14) 0.09462(7) 0.0118(2) Uani 1 d . . . C9 C 0.12218(9) 1.04061(17) 0.11174(9) 0.0146(3) Uani 1 d . . . H9A H 0.0888 1.0384 0.1586 0.018 Uiso 1 calc R . . H9B H 0.0858 1.0795 0.0658 0.018 Uiso 1 calc R . . C10 C 0.19569(10) 1.14804(17) 0.12796(9) 0.0142(3) Uani 1 d . . . H10A H 0.1759 1.2478 0.1478 0.017 Uiso 1 calc R . . H10B H 0.2358 1.1032 0.1695 0.017 Uiso 1 calc R . . N11 N 0.23846(8) 1.17357(15) 0.05380(8) 0.0115(2) Uani 1 d . . . H11A H 0.2034(12) 1.203(2) 0.0165(12) 0.020(5) Uiso 1 d . . . H11B H 0.2583(12) 1.083(2) 0.0379(11) 0.020(5) Uiso 1 d . . . C12 C 0.30843(9) 1.28716(17) 0.06516(9) 0.0155(3) Uani 1 d . . . H12A H 0.3541 1.2424 0.1010 0.019 Uiso 1 calc R . . H12B H 0.2881 1.3809 0.0909 0.019 Uiso 1 calc R . . C13 C 0.34263(9) 1.33139(18) -0.01314(10) 0.0161(3) Uani 1 d . . . H13A H 0.3655 1.2381 -0.0372 0.019 Uiso 1 calc R . . H13B H 0.3894 1.4048 -0.0022 0.019 Uiso 1 calc R . . C14 C 0.27756(9) 1.40423(17) -0.07317(10) 0.0154(3) Uani 1 d . . . H14A H 0.2470 1.4859 -0.0465 0.019 Uiso 1 calc R . . H14B H 0.3064 1.4527 -0.1165 0.019 Uiso 1 calc R . . C15 C 0.13975(9) 1.36047(17) -0.14025(9) 0.0137(3) Uani 1 d . . . H15A H 0.1075 1.2848 -0.1744 0.016 Uiso 1 calc R . . H15B H 0.1534 1.4485 -0.1742 0.016 Uiso 1 calc R . . C16 C 0.08560(9) 1.41711(16) -0.07625(9) 0.0113(3) Uani 1 d . . . N17 N 0.02620(8) 1.51684(15) -0.10149(8) 0.0145(2) Uani 1 d D . . H17A H 0.0247(13) 1.554(2) -0.1495(10) 0.026(5) Uiso 1 d D . . H17B H -0.0109(11) 1.552(2) -0.0709(10) 0.019(5) Uiso 1 d D . . O161 O 0.09540(6) 1.36839(12) -0.00687(6) 0.0143(2) Uani 1 d . . . C18 C 0.33521(9) 0.89142(18) -0.10199(9) 0.0145(3) Uani 1 d . . . H18A H 0.3682 0.9702 -0.1282 0.017 Uiso 1 calc R . . H18B H 0.3339 0.7968 -0.1348 0.017 Uiso 1 calc R . . C19 C 0.37658(9) 0.85697(17) -0.01963(9) 0.0129(3) Uani 1 d . . . N20 N 0.43331(9) 0.74348(16) -0.01473(9) 0.0185(3) Uani 1 d D . . H20A H 0.4573(12) 0.724(2) 0.0320(10) 0.027(5) Uiso 1 d D . . H20B H 0.4439(13) 0.693(2) -0.0575(10) 0.028(5) Uiso 1 d D . . O191 O 0.35857(7) 0.93150(12) 0.03891(6) 0.0155(2) Uani 1 d . . . C21 C 0.15509(10) 0.78836(18) 0.16698(9) 0.0161(3) Uani 1 d . . . H21A H 0.0989 0.7452 0.1737 0.019 Uiso 1 calc R . . H21B H 0.1705 0.8555 0.2134 0.019 Uiso 1 calc R . . C22 C 0.21761(10) 0.65667(17) 0.16721(9) 0.0139(3) Uani 1 d . . . N23 N 0.28891(9) 0.68798(16) 0.13422(9) 0.0183(3) Uani 1 d D . . H23A H 0.2959(12) 0.7811(19) 0.1123(11) 0.025(5) Uiso 1 d D . . H23B H 0.3302(11) 0.625(2) 0.1425(12) 0.026(5) Uiso 1 d D . . O221 O 0.20427(7) 0.53302(13) 0.19942(7) 0.0190(2) Uani 1 d . . . C100 C 0.47891(11) 0.9949(3) 0.19590(11) 0.0323(4) Uani 1 d . . . H10C H 0.4930 1.1026 0.2080 0.039 Uiso 1 calc R . . H10D H 0.4240 0.9710 0.2145 0.039 Uiso 1 calc R . . H10E H 0.4772 0.9783 0.1383 0.039 Uiso 1 calc R . . O101 O 0.54087(8) 0.89671(16) 0.23519(8) 0.0255(3) Uani 1 d . . . H10F H 0.5273(14) 0.808(3) 0.2213(14) 0.038(7) Uiso 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I 0.01339(4) 0.01742(5) 0.01513(5) -0.00167(4) 0.00185(3) 0.00065(4) N1 0.0103(5) 0.0099(5) 0.0152(6) 0.0002(5) 0.0034(4) 0.0022(4) C2 0.0173(7) 0.0135(7) 0.0131(7) 0.0033(5) 0.0063(5) 0.0053(6) C3 0.0180(7) 0.0130(7) 0.0102(6) 0.0000(5) 0.0015(5) 0.0047(5) N4 0.0129(5) 0.0098(5) 0.0114(6) 0.0023(4) 0.0015(4) 0.0022(4) C5 0.0171(7) 0.0085(6) 0.0163(7) 0.0004(5) 0.0002(6) 0.0006(5) C6 0.0146(7) 0.0130(7) 0.0160(7) 0.0017(6) -0.0019(5) -0.0006(5) C7 0.0135(7) 0.0147(7) 0.0182(7) 0.0026(6) 0.0007(6) -0.0029(5) N8 0.0137(6) 0.0098(5) 0.0120(6) 0.0022(5) 0.0014(5) 0.0006(4) C9 0.0148(7) 0.0131(7) 0.0167(7) 0.0018(5) 0.0054(5) 0.0026(5) C10 0.0208(7) 0.0129(7) 0.0093(7) -0.0010(5) 0.0035(5) 0.0022(6) N11 0.0126(6) 0.0100(6) 0.0118(6) -0.0011(5) 0.0004(5) -0.0003(5) C12 0.0146(7) 0.0124(7) 0.0191(8) -0.0023(6) -0.0016(6) -0.0041(5) C13 0.0109(6) 0.0131(7) 0.0241(8) 0.0008(6) 0.0013(6) -0.0010(5) C14 0.0139(7) 0.0095(6) 0.0233(8) 0.0013(6) 0.0040(6) 0.0001(5) C15 0.0147(7) 0.0139(7) 0.0129(7) 0.0015(5) 0.0036(5) 0.0039(5) C16 0.0095(6) 0.0107(6) 0.0136(7) -0.0010(5) 0.0016(5) -0.0009(5) N17 0.0140(5) 0.0158(6) 0.0143(6) 0.0023(5) 0.0038(5) 0.0054(5) O161 0.0130(5) 0.0176(5) 0.0125(5) 0.0016(4) 0.0026(4) 0.0032(4) C18 0.0160(7) 0.0140(7) 0.0140(7) 0.0012(6) 0.0037(5) 0.0051(6) C19 0.0109(6) 0.0117(7) 0.0163(7) 0.0006(5) 0.0027(5) -0.0007(5) N20 0.0196(7) 0.0205(7) 0.0154(7) -0.0009(6) 0.0008(5) 0.0093(5) O191 0.0158(5) 0.0150(5) 0.0155(5) -0.0030(4) 0.0007(4) 0.0019(4) C21 0.0190(7) 0.0156(7) 0.0142(7) 0.0038(6) 0.0049(6) 0.0032(6) C22 0.0186(7) 0.0130(7) 0.0098(7) -0.0010(5) -0.0011(5) 0.0002(6) N23 0.0159(6) 0.0139(6) 0.0254(7) 0.0043(5) 0.0030(5) 0.0031(5) O221 0.0264(6) 0.0131(5) 0.0174(5) 0.0030(4) 0.0022(4) -0.0002(4) C100 0.0215(8) 0.0516(13) 0.0233(9) -0.0054(9) -0.0005(7) -0.0034(9) O101 0.0261(6) 0.0252(7) 0.0251(7) -0.0109(5) 0.0016(5) -0.0042(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C15 1.4552(18) . ? N1 C2 1.4735(19) . ? N1 C14 1.4742(19) . ? C2 C3 1.517(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N4 1.4677(18) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N4 C18 1.4554(18) . ? N4 C5 1.4689(19) . ? C5 C6 1.535(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.526(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N8 1.4703(19) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? N8 C21 1.4682(19) . ? N8 C9 1.4757(19) . ? C9 C10 1.509(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N11 1.4911(19) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? N11 C12 1.4932(19) . ? N11 H11A 0.85(2) . ? N11 H11B 0.90(2) . ? C12 C13 1.520(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.529(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.521(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 O161 1.2420(17) . ? C16 N17 1.3301(19) . ? N17 H17A 0.869(15) . ? N17 H17B 0.874(14) . ? C18 C19 1.519(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 O191 1.2342(18) . ? C19 N20 1.3382(19) . ? N20 H20A 0.865(15) . ? N20 H20B 0.874(15) . ? C21 C22 1.520(2) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 O221 1.2297(18) . ? C22 N23 1.339(2) . ? N23 H23A 0.900(15) . ? N23 H23B 0.862(15) . ? C100 O101 1.429(2) . ? C100 H10C 0.9800 . ? C100 H10D 0.9800 . ? C100 H10E 0.9800 . ? O101 H10F 0.83(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 C15 N1 C2 109.86(12) . . ? C15 N1 C14 111.81(11) . . ? C2 N1 C14 112.08(11) . . ? N1 C2 C3 111.72(12) . . ? N1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? N1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? N4 C3 C2 111.15(12) . . ? N4 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? N4 C3 H3B 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C18 N4 C3 111.33(11) . . ? C18 N4 C5 109.91(11) . . ? C3 N4 C5 112.31(12) . . ? N4 C5 C6 113.07(12) . . ? N4 C5 H5A 109.0 . . ? C6 C5 H5A 109.0 . . ? N4 C5 H5B 109.0 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C7 C6 C5 112.24(12) . . ? C7 C6 H6A 109.2 . . ? C5 C6 H6A 109.2 . . ? C7 C6 H6B 109.2 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? N8 C7 C6 112.17(12) . . ? N8 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? N8 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C21 N8 C7 110.54(12) . . ? C21 N8 C9 110.64(12) . . ? C7 N8 C9 111.48(12) . . ? N8 C9 C10 111.27(12) . . ? N8 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? N8 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? N11 C10 C9 110.20(12) . . ? N11 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? N11 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C10 N11 C12 112.48(12) . . ? C10 N11 H11A 110.2(13) . . ? C12 N11 H11A 110.1(13) . . ? C10 N11 H11B 108.7(12) . . ? C12 N11 H11B 109.6(12) . . ? H11A N11 H11B 105.6(17) . . ? N11 C12 C13 112.07(12) . . ? N11 C12 H12A 109.2 . . ? C13 C12 H12A 109.2 . . ? N11 C12 H12B 109.2 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C12 C13 C14 113.89(12) . . ? C12 C13 H13A 108.8 . . ? C14 C13 H13A 108.8 . . ? C12 C13 H13B 108.8 . . ? C14 C13 H13B 108.8 . . ? H13A C13 H13B 107.7 . . ? N1 C14 C13 111.57(12) . . ? N1 C14 H14A 109.3 . . ? C13 C14 H14A 109.3 . . ? N1 C14 H14B 109.3 . . ? C13 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? N1 C15 C16 112.61(12) . . ? N1 C15 H15A 109.1 . . ? C16 C15 H15A 109.1 . . ? N1 C15 H15B 109.1 . . ? C16 C15 H15B 109.1 . . ? H15A C15 H15B 107.8 . . ? O161 C16 N17 123.69(13) . . ? O161 C16 C15 121.56(13) . . ? N17 C16 C15 114.71(13) . . ? C16 N17 H17A 120.1(14) . . ? C16 N17 H17B 123.0(13) . . ? H17A N17 H17B 116.8(18) . . ? N4 C18 C19 110.17(12) . . ? N4 C18 H18A 109.6 . . ? C19 C18 H18A 109.6 . . ? N4 C18 H18B 109.6 . . ? C19 C18 H18B 109.6 . . ? H18A C18 H18B 108.1 . . ? O191 C19 N20 122.60(14) . . ? O191 C19 C18 121.01(13) . . ? N20 C19 C18 116.38(13) . . ? C19 N20 H20A 116.7(14) . . ? C19 N20 H20B 119.8(14) . . ? H20A N20 H20B 123.5(19) . . ? N8 C21 C22 114.41(12) . . ? N8 C21 H21A 108.7 . . ? C22 C21 H21A 108.7 . . ? N8 C21 H21B 108.7 . . ? C22 C21 H21B 108.7 . . ? H21A C21 H21B 107.6 . . ? O221 C22 N23 123.09(15) . . ? O221 C22 C21 121.30(14) . . ? N23 C22 C21 115.51(13) . . ? C22 N23 H23A 119.5(13) . . ? C22 N23 H23B 118.2(14) . . ? H23A N23 H23B 121.3(18) . . ? O101 C100 H10C 109.5 . . ? O101 C100 H10D 109.5 . . ? H10C C100 H10D 109.5 . . ? O101 C100 H10E 109.5 . . ? H10C C100 H10E 109.5 . . ? H10D C100 H10E 109.5 . . ? C100 O101 H10F 105.4(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N1 C2 C3 -88.64(14) . . . . ? C14 N1 C2 C3 146.41(12) . . . . ? N1 C2 C3 N4 -68.87(15) . . . . ? C2 C3 N4 C18 -79.69(15) . . . . ? C2 C3 N4 C5 156.57(12) . . . . ? C18 N4 C5 C6 166.01(12) . . . . ? C3 N4 C5 C6 -69.46(15) . . . . ? N4 C5 C6 C7 -122.17(14) . . . . ? C5 C6 C7 N8 70.20(16) . . . . ? C6 C7 N8 C21 -160.51(12) . . . . ? C6 C7 N8 C9 75.99(15) . . . . ? C21 N8 C9 C10 95.28(14) . . . . ? C7 N8 C9 C10 -141.28(12) . . . . ? N8 C9 C10 N11 68.55(15) . . . . ? C9 C10 N11 C12 176.29(12) . . . . ? C10 N11 C12 C13 -171.02(12) . . . . ? N11 C12 C13 C14 59.70(17) . . . . ? C15 N1 C14 C13 158.91(12) . . . . ? C2 N1 C14 C13 -77.22(15) . . . . ? C12 C13 C14 N1 -72.72(16) . . . . ? C2 N1 C15 C16 161.52(12) . . . . ? C14 N1 C15 C16 -73.38(15) . . . . ? N1 C15 C16 O161 -19.0(2) . . . . ? N1 C15 C16 N17 163.32(13) . . . . ? C3 N4 C18 C19 160.41(12) . . . . ? C5 N4 C18 C19 -74.50(15) . . . . ? N4 C18 C19 O191 -31.44(19) . . . . ? N4 C18 C19 N20 149.07(13) . . . . ? C7 N8 C21 C22 82.55(15) . . . . ? C9 N8 C21 C22 -153.46(13) . . . . ? N8 C21 C22 O221 -145.60(14) . . . . ? N8 C21 C22 N23 37.91(19) . . . . ? _diffrn_measured_fraction_theta_max 0.934 _diffrn_reflns_theta_full 33.11 _diffrn_measured_fraction_theta_full 0.934 _refine_diff_density_max 0.684 _refine_diff_density_min -0.601 _refine_diff_density_rms 0.095 #==END data_compound_2 _database_code_depnum_ccdc_archive 'CCDC 689801' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H26.50 Cl I N4 O2.25' _chemical_formula_weight 449.24 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' 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 P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 13.479(14) _cell_length_b 10.091(12) _cell_length_c 14.314(14) _cell_angle_alpha 90.00 _cell_angle_beta 108.57(1) _cell_angle_gamma 90.00 _cell_volume 1846(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block shaped' _exptl_crystal_colour brown-red _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.617 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 906 _exptl_absorpt_coefficient_mu 1.894 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_T_max 1.00 _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 'image plate ' _diffrn_measurement_method '95 frames at 2teta intervals' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7202 _diffrn_reflns_av_R_equivalents 0.0572 _diffrn_reflns_av_sigmaI/netI 0.0543 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 25.71 _reflns_number_total 3284 _reflns_number_gt 2769 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XDS (Kabsch, 1991)' _computing_cell_refinement 'XDS (Kabsch, 1991)' _computing_data_reduction 'XDS (Kabsch, 1991)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0425P)^2^+11.5703P] 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 constrained _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3284 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0853 _refine_ls_R_factor_gt 0.0684 _refine_ls_wR_factor_ref 0.1508 _refine_ls_wR_factor_gt 0.1437 _refine_ls_goodness_of_fit_ref 1.208 _refine_ls_restrained_S_all 1.208 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I I 0.18373(4) 0.02992(6) 0.25337(4) 0.0418(2) Uani 1 d . . . Cl Cl 0.32021(12) 0.44423(15) 0.09910(12) 0.0231(4) Uani 1 d . . . N14 N -0.0604(4) 0.2407(5) 0.0061(4) 0.0189(11) Uani 1 d . . . H14 H -0.0916 0.1773 0.0325 0.023 Uiso 1 calc R . . C13 C 0.0273(5) 0.1742(6) -0.0201(5) 0.0220(15) Uani 1 d . . . H13A H -0.0008 0.1039 -0.0673 0.026 Uiso 1 calc R . . H13B H 0.0760 0.1351 0.0386 0.026 Uiso 1 calc R . . C12 C 0.0846(5) 0.2746(6) -0.0641(5) 0.0219(14) Uani 1 d . . . H12A H 0.1321 0.3260 -0.0113 0.026 Uiso 1 calc R . . H12B H 0.1260 0.2277 -0.0978 0.026 Uiso 1 calc R . . N11 N 0.0121(4) 0.3649(5) -0.1337(4) 0.0156(11) Uani 1 d . . . C16 C -0.0926(5) 0.3659(6) -0.1525(5) 0.0178(13) Uani 1 d . . . C15 C -0.1394(5) 0.2845(6) -0.0883(5) 0.0212(14) Uani 1 d . . . H15A H -0.1929 0.3365 -0.0732 0.025 Uiso 1 calc R . . H15B H -0.1731 0.2069 -0.1249 0.025 Uiso 1 calc R . . C19 C 0.0602(5) 0.4649(6) -0.1814(5) 0.0206(13) Uani 1 d . . . H19A H 0.0080 0.4983 -0.2402 0.025 Uiso 1 calc R . . H19B H 0.1156 0.4238 -0.2011 0.025 Uiso 1 calc R . . C18 C -0.1056(5) 0.4195(6) 0.1110(5) 0.0234(14) Uani 1 d . . . H18A H -0.1410 0.3586 0.1422 0.028 Uiso 1 calc R . . H18B H -0.1568 0.4533 0.0517 0.028 Uiso 1 calc R . . C17 C -0.0207(5) 0.3459(6) 0.0836(5) 0.0196(14) Uani 1 d . . . H17A H 0.0198 0.4096 0.0601 0.024 Uiso 1 calc R . . H17B H 0.0261 0.3049 0.1424 0.024 Uiso 1 calc R . . O100 O -0.1523(4) 0.4327(5) -0.2187(4) 0.0367(13) Uani 1 d . . . C23 C -0.2357(6) 0.1235(9) 0.3853(6) 0.043(2) Uani 1 d . . . H23A H -0.2900 0.0601 0.3848 0.052 Uiso 1 calc R . . H23B H -0.2693 0.2022 0.3505 0.052 Uiso 1 calc R . . N24 N -0.1656(5) 0.0651(6) 0.3329(4) 0.0325(15) Uani 1 d . . . H24 H -0.2058 0.0469 0.2700 0.039 Uiso 1 calc R . . C25 C -0.0898(6) 0.1697(9) 0.3285(6) 0.0396(19) Uani 1 d . . . H25A H -0.1274 0.2418 0.2874 0.048 Uiso 1 calc R . . H25B H -0.0411 0.1335 0.2979 0.048 Uiso 1 calc R . . C27 C -0.1210(6) -0.0643(8) 0.3811(6) 0.0343(18) Uani 1 d . . . H27A H -0.0826 -0.0478 0.4499 0.041 Uiso 1 calc R . . H27B H -0.1783 -0.1237 0.3787 0.041 Uiso 1 calc R . . C28 C -0.0497(8) -0.1316(10) 0.3343(6) 0.053(2) Uani 1 d . . . H28A H 0.0018 -0.0686 0.3274 0.063 Uiso 1 calc R . . H28B H -0.0901 -0.1620 0.2690 0.063 Uiso 1 calc R . . N21 N -0.0696(5) 0.2107(6) 0.5024(5) 0.0351(16) Uani 1 d . . . C22 C -0.1748(6) 0.1594(10) 0.4911(6) 0.045(2) Uani 1 d . . . H22A H -0.2136 0.2258 0.5141 0.054 Uiso 1 calc R . . H22B H -0.1687 0.0814 0.5322 0.054 Uiso 1 calc R . . O200 O 0.0557(5) 0.2770(7) 0.4387(5) 0.0617(19) Uani 1 d . . . C26 C -0.0290(6) 0.2240(8) 0.4289(6) 0.0381(19) Uani 1 d . . . C29 C -0.0069(7) 0.2505(9) 0.6039(6) 0.047(2) Uani 1 d . . . H29A H -0.0527 0.2910 0.6361 0.056 Uiso 1 calc R . . H29B H 0.0445 0.3161 0.6006 0.056 Uiso 1 calc R . . O161 O 0.363(2) 0.024(2) 0.490(2) 0.066(9) Uani 0.25 d P . . 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 0.0433(3) 0.0464(3) 0.0406(3) -0.0153(2) 0.0203(2) -0.0133(2) Cl 0.0250(8) 0.0192(7) 0.0237(8) -0.0021(6) 0.0059(6) 0.0067(6) N14 0.023(3) 0.013(2) 0.025(3) 0.001(2) 0.013(2) -0.002(2) C13 0.025(3) 0.006(3) 0.031(4) 0.001(2) 0.004(3) 0.004(2) C12 0.018(3) 0.021(3) 0.026(4) -0.003(3) 0.007(3) 0.003(3) N11 0.016(2) 0.013(2) 0.017(3) 0.002(2) 0.004(2) 0.001(2) C16 0.016(3) 0.017(3) 0.018(3) -0.005(2) 0.001(3) 0.002(2) C15 0.010(3) 0.027(3) 0.025(4) -0.006(3) 0.004(3) -0.007(2) C19 0.030(3) 0.020(3) 0.019(3) -0.003(3) 0.017(3) -0.006(3) C18 0.030(3) 0.019(3) 0.025(4) -0.003(3) 0.014(3) -0.004(3) C17 0.027(3) 0.016(3) 0.015(3) -0.002(2) 0.006(3) -0.003(3) O100 0.027(3) 0.050(3) 0.027(3) 0.011(2) -0.001(2) 0.010(2) C23 0.034(4) 0.050(5) 0.038(5) -0.005(4) 0.002(4) 0.010(4) N24 0.029(3) 0.042(4) 0.017(3) -0.005(3) -0.007(3) 0.000(3) C25 0.038(4) 0.055(5) 0.023(4) -0.002(4) 0.007(3) -0.004(4) C27 0.033(4) 0.041(4) 0.023(4) 0.000(3) 0.001(3) 0.001(3) C28 0.059(6) 0.069(6) 0.027(4) -0.009(4) 0.009(4) 0.012(5) N21 0.040(4) 0.038(4) 0.021(3) -0.007(3) 0.001(3) 0.001(3) C22 0.041(5) 0.064(6) 0.028(4) -0.010(4) 0.007(4) 0.000(4) O200 0.052(4) 0.087(5) 0.048(4) -0.016(4) 0.019(3) -0.028(4) C26 0.035(4) 0.043(5) 0.032(4) -0.006(4) 0.004(4) 0.000(4) C29 0.051(5) 0.051(5) 0.024(4) -0.012(4) -0.007(4) 0.012(4) O161 0.068(17) 0.041(13) 0.061(17) 0.008(13) -0.019(15) -0.013(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N14 C15 1.496(8) . ? N14 C17 1.506(8) . ? N14 C13 1.507(9) . ? N14 H14 0.9100 . ? C13 C12 1.526(10) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C12 N11 1.469(8) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? N11 C16 1.350(8) . ? N11 C19 1.479(8) . ? C16 O100 1.231(8) . ? C16 C15 1.512(9) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C19 C18 1.535(9) 3_565 ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C18 C17 1.518(9) . ? C18 C19 1.535(9) 3_565 ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C23 N24 1.500(11) . ? C23 C22 1.519(11) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? N24 C25 1.484(11) . ? N24 C27 1.510(10) . ? N24 H24 0.9100 . ? C25 C26 1.512(11) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C27 C28 1.497(12) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.540(12) 3_556 ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? N21 C26 1.338(12) . ? N21 C22 1.470(11) . ? N21 C29 1.485(9) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? O200 C26 1.227(10) . ? C29 C28 1.540(12) 3_556 ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? 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 C15 N14 C17 116.2(5) . . ? C15 N14 C13 107.2(5) . . ? C17 N14 C13 111.9(5) . . ? C15 N14 H14 107.0 . . ? C17 N14 H14 107.0 . . ? C13 N14 H14 107.0 . . ? N14 C13 C12 110.3(5) . . ? N14 C13 H13A 109.6 . . ? C12 C13 H13A 109.6 . . ? N14 C13 H13B 109.6 . . ? C12 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? N11 C12 C13 112.2(5) . . ? N11 C12 H12A 109.2 . . ? C13 C12 H12A 109.2 . . ? N11 C12 H12B 109.2 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C16 N11 C12 124.5(5) . . ? C16 N11 C19 119.2(5) . . ? C12 N11 C19 116.2(5) . . ? O100 C16 N11 122.9(7) . . ? O100 C16 C15 117.9(6) . . ? N11 C16 C15 119.2(5) . . ? N14 C15 C16 113.2(5) . . ? N14 C15 H15A 108.9 . . ? C16 C15 H15A 108.9 . . ? N14 C15 H15B 108.9 . . ? C16 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? N11 C19 C18 110.9(5) . 3_565 ? N11 C19 H19A 109.5 . . ? C18 C19 H19A 109.5 3_565 . ? N11 C19 H19B 109.5 . . ? C18 C19 H19B 109.5 3_565 . ? H19A C19 H19B 108.0 . . ? C17 C18 C19 111.5(5) . 3_565 ? C17 C18 H18A 109.3 . . ? C19 C18 H18A 109.3 3_565 . ? C17 C18 H18B 109.3 . . ? C19 C18 H18B 109.3 3_565 . ? H18A C18 H18B 108.0 . . ? N14 C17 C18 114.5(5) . . ? N14 C17 H17A 108.6 . . ? C18 C17 H17A 108.6 . . ? N14 C17 H17B 108.6 . . ? C18 C17 H17B 108.6 . . ? H17A C17 H17B 107.6 . . ? N24 C23 C22 111.4(6) . . ? N24 C23 H23A 109.3 . . ? C22 C23 H23A 109.3 . . ? N24 C23 H23B 109.3 . . ? C22 C23 H23B 109.3 . . ? H23A C23 H23B 108.0 . . ? C25 N24 C23 107.1(6) . . ? C25 N24 C27 117.1(6) . . ? C23 N24 C27 109.5(6) . . ? C25 N24 H24 107.6 . . ? C23 N24 H24 107.6 . . ? C27 N24 H24 107.6 . . ? N24 C25 C26 112.9(7) . . ? N24 C25 H25A 109.0 . . ? C26 C25 H25A 109.0 . . ? N24 C25 H25B 109.0 . . ? C26 C25 H25B 109.0 . . ? H25A C25 H25B 107.8 . . ? C28 C27 N24 114.1(7) . . ? C28 C27 H27A 108.7 . . ? N24 C27 H27A 108.7 . . ? C28 C27 H27B 108.7 . . ? N24 C27 H27B 108.7 . . ? H27A C27 H27B 107.6 . . ? C27 C28 C29 111.6(8) . 3_556 ? C27 C28 H28A 109.3 . . ? C29 C28 H28A 109.3 3_556 . ? C27 C28 H28B 109.3 . . ? C29 C28 H28B 109.3 3_556 . ? H28A C28 H28B 108.0 . . ? C26 N21 C22 124.8(6) . . ? C26 N21 C29 119.7(7) . . ? C22 N21 C29 115.5(8) . . ? N21 C22 C23 112.9(8) . . ? N21 C22 H22A 109.0 . . ? C23 C22 H22A 109.0 . . ? N21 C22 H22B 109.0 . . ? C23 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? O200 C26 N21 123.5(8) . . ? O200 C26 C25 118.0(9) . . ? N21 C26 C25 118.5(7) . . ? N21 C29 C28 111.9(7) . 3_556 ? N21 C29 H29A 109.2 . . ? C28 C29 H29A 109.2 3_556 . ? N21 C29 H29B 109.2 . . ? C28 C29 H29B 109.2 3_556 . ? H29A C29 H29B 107.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N14 C13 C12 66.0(6) . . . . ? C17 N14 C13 C12 -62.5(7) . . . . ? N14 C13 C12 N11 -42.2(7) . . . . ? C13 C12 N11 C16 4.1(9) . . . . ? C13 C12 N11 C19 -179.2(5) . . . . ? C12 N11 C16 O100 -172.0(6) . . . . ? C19 N11 C16 O100 11.4(9) . . . . ? C12 N11 C16 C15 9.6(9) . . . . ? C19 N11 C16 C15 -167.0(5) . . . . ? C17 N14 C15 C16 73.9(7) . . . . ? C13 N14 C15 C16 -52.1(6) . . . . ? O100 C16 C15 N14 -162.7(6) . . . . ? N11 C16 C15 N14 15.7(8) . . . . ? C16 N11 C19 C18 98.7(7) . . . 3_565 ? C12 N11 C19 C18 -78.2(7) . . . 3_565 ? C15 N14 C17 C18 54.6(8) . . . . ? C13 N14 C17 C18 178.3(5) . . . . ? C19 C18 C17 N14 -173.6(5) 3_565 . . . ? C22 C23 N24 C25 -63.6(9) . . . . ? C22 C23 N24 C27 64.3(9) . . . . ? C23 N24 C25 C26 55.9(8) . . . . ? C27 N24 C25 C26 -67.4(9) . . . . ? C25 N24 C27 C28 -58.0(9) . . . . ? C23 N24 C27 C28 179.9(7) . . . . ? N24 C27 C28 C29 170.9(6) . . . 3_556 ? C26 N21 C22 C23 -0.7(12) . . . . ? C29 N21 C22 C23 178.7(7) . . . . ? N24 C23 C22 N21 36.5(10) . . . . ? C22 N21 C26 O200 173.9(8) . . . . ? C29 N21 C26 O200 -5.5(13) . . . . ? C22 N21 C26 C25 -6.8(12) . . . . ? C29 N21 C26 C25 173.8(7) . . . . ? N24 C25 C26 O200 157.2(8) . . . . ? N24 C25 C26 N21 -22.1(11) . . . . ? C26 N21 C29 C28 -96.6(10) . . . 3_556 ? C22 N21 C29 C28 84.0(10) . . . 3_556 ? _diffrn_measured_fraction_theta_max 0.878 _diffrn_reflns_theta_full 25.71 _diffrn_measured_fraction_theta_full 0.878 _refine_diff_density_max 1.606 _refine_diff_density_min -1.050 _refine_diff_density_rms 0.133 ##==END data_compound_3 _database_code_depnum_ccdc_archive 'CCDC 689802' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H52 I7 N4 O10 P2' _chemical_formula_weight 1506.94 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' P P 0.1023 0.0942 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.9857(8) _cell_length_b 13.1654(10) _cell_length_c 16.3597(12) _cell_angle_alpha 96.362(4) _cell_angle_beta 99.913(4) _cell_angle_gamma 95.544(4) _cell_volume 2300.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block shaped' _exptl_crystal_colour brown-red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.176 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1410 _exptl_absorpt_coefficient_mu 4.838 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4445 _exptl_absorpt_correction_T_max 0.4445 _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 65001 _diffrn_reflns_av_R_equivalents 0.0584 _diffrn_reflns_av_sigmaI/netI 0.0599 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 26.57 _reflns_number_total 9497 _reflns_number_gt 6163 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0717P)^2^+36.8160P] 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 constrained _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9497 _refine_ls_number_parameters 428 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1170 _refine_ls_R_factor_gt 0.0652 _refine_ls_wR_factor_ref 0.1886 _refine_ls_wR_factor_gt 0.1504 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 1.23066(9) 0.73268(6) 0.75756(5) 0.0411(2) Uani 1 d . . . I3 I 0.70346(9) 0.58973(7) 0.63831(5) 0.0450(2) Uani 1 d . . . I2 I 0.95873(8) 0.65579(6) 0.70100(5) 0.0347(2) Uani 1 d . . . I5 I 0.35229(8) 0.83144(6) 0.35739(6) 0.0428(2) Uani 1 d . . . I4 I 0.43836(9) 0.78119(7) 0.52038(6) 0.0494(3) Uani 1 d . . . I7 I 0.43269(13) 0.95372(8) 0.05197(7) 0.0679(4) Uani 1 d . . . I6 I 0.24824(11) 0.89062(7) 0.18719(6) 0.0576(3) Uani 1 d . . . N21 N 0.6625(9) 0.4722(7) 0.9122(5) 0.028(2) Uani 1 d . A 1 H21 H 0.6260 0.5140 0.9463 0.033 Uiso 1 calc R A 1 C22 C 0.6972(10) 0.3886(8) 0.9581(6) 0.027(2) Uani 1 d . . 1 H22A H 0.7419 0.3447 0.9252 0.032 Uiso 1 calc R . 1 H22B H 0.6221 0.3477 0.9647 0.032 Uiso 1 calc R . 1 C23 C 0.2233(12) 0.5780(9) 0.9568(7) 0.033(3) Uani 1 d . . 1 H23A H 0.2279 0.6344 0.9235 0.039 Uiso 1 calc R . 1 H23B H 0.1374 0.5637 0.9632 0.039 Uiso 1 calc R . 1 N24 N 0.2605(9) 0.4840(7) 0.9101(5) 0.027(2) Uani 1 d . A 1 H24 H 0.2666 0.4353 0.9455 0.032 Uiso 1 calc R A 1 C25 C 0.3882(10) 0.5060(8) 0.8867(7) 0.027(2) Uani 1 d . A 1 H25A H 0.3825 0.5528 0.8448 0.032 Uiso 1 calc R A 1 H25B H 0.4464 0.5398 0.9358 0.032 Uiso 1 calc R A 1 C26 C 0.4367(11) 0.4116(8) 0.8537(7) 0.031(3) Uani 1 d . A 1 H26A H 0.3815 0.3796 0.8027 0.037 Uiso 1 calc R A 1 H26B H 0.4390 0.3630 0.8943 0.037 Uiso 1 calc R A 1 C27 C 0.5668(11) 0.4366(8) 0.8357(7) 0.031(3) Uani 1 d . A 1 H27A H 0.5906 0.3757 0.8062 0.037 Uiso 1 calc R A 1 H27B H 0.5651 0.4897 0.7990 0.037 Uiso 1 calc R A 1 C28 C 0.1630(11) 0.4400(9) 0.8349(6) 0.028(3) Uani 1 d . A 1 H28A H 0.1378 0.4952 0.8036 0.034 Uiso 1 calc R A 1 H28B H 0.1986 0.3923 0.7988 0.034 Uiso 1 calc R A 1 C29 C 0.0505(11) 0.3850(9) 0.8583(6) 0.029(3) Uani 1 d . A 1 C35 C 0.7681(11) 0.5372(8) 0.8918(7) 0.029(3) Uani 1 d . A 1 H35A H 0.7708 0.5232 0.8327 0.035 Uiso 1 calc R A 1 H35B H 0.8461 0.5228 0.9237 0.035 Uiso 1 calc R A 1 P36 P 0.7451(3) 0.6695(2) 0.91823(18) 0.0284(7) Uani 1 d . A 1 O291 O 0.0184(7) 0.4053(6) 0.9262(5) 0.0333(19) Uani 1 d . A 1 O292 O -0.0149(10) 0.3137(9) 0.7972(6) 0.062(3) Uani 1 d . A 1 O361 O 0.7299(8) 0.6918(5) 1.0072(5) 0.0308(18) Uani 1 d . A 1 O362 O 0.6318(9) 0.6858(6) 0.8527(5) 0.038(2) Uani 1 d . A 1 O363 O 0.8544(9) 0.7406(6) 0.8963(5) 0.043(2) Uani 1 d . A 1 C335 C 0.9692(14) 0.7811(12) 0.9542(11) 0.057(4) Uani 1 d . A 1 H33A H 1.0282 0.7308 0.9549 0.068 Uiso 1 calc R A 1 H33B H 0.9524 0.7958 1.0104 0.068 Uiso 1 calc R A 1 C336 C 1.0216(17) 0.8768(11) 0.9263(10) 0.066(5) Uani 1 d . A 1 H33C H 1.0312 0.8627 0.8691 0.099 Uiso 1 calc R A 1 H33D H 1.1011 0.9012 0.9608 0.099 Uiso 1 calc R A 1 H33E H 0.9661 0.9284 0.9309 0.099 Uiso 1 calc R A 1 C333 C 0.5912(14) 0.7873(10) 0.8505(8) 0.045(3) Uani 1 d . A 1 H33F H 0.6512 0.8375 0.8885 0.054 Uiso 1 calc R A 1 H33G H 0.5118 0.7877 0.8688 0.054 Uiso 1 calc R A 1 C334 C 0.5785(18) 0.8161(12) 0.7636(10) 0.067(5) Uani 1 d . A 1 H33H H 0.6575 0.8171 0.7461 0.101 Uiso 1 calc R A 1 H33I H 0.5508 0.8830 0.7629 0.101 Uiso 1 calc R A 1 H33J H 0.5188 0.7665 0.7261 0.101 Uiso 1 calc R A 1 N1 N 0.7987(9) 0.8939(6) 0.4808(5) 0.025(2) Uani 1 d . B 2 H1 H 0.8776 0.9055 0.4711 0.030 Uiso 1 calc R B 2 C2 C 0.7314(11) 0.9773(8) 0.4504(7) 0.029(3) Uani 1 d . B 2 H2A H 0.7675 1.0414 0.4849 0.035 Uiso 1 calc R B 2 H2B H 0.6456 0.9645 0.4575 0.035 Uiso 1 calc R B 2 C3 C 0.7326(11) 0.9903(9) 0.3596(7) 0.032(3) Uani 1 d . . 2 H3A H 0.7120 1.0586 0.3503 0.039 Uiso 1 calc R . 2 H3B H 0.6685 0.9408 0.3244 0.039 Uiso 1 calc R . 2 N4 N 1.1428(9) 1.0241(7) 0.6671(5) 0.026(2) Uani 1 d . . 2 H4 H 1.1238 1.0877 0.6565 0.031 Uiso 1 calc R . 2 C5 C 1.0383(10) 0.9447(8) 0.6155(7) 0.026(2) Uani 1 d . B 2 H5A H 1.0467 0.9382 0.5571 0.031 Uiso 1 calc R B 2 H5B H 1.0457 0.8781 0.6348 0.031 Uiso 1 calc R B 2 C6 C 0.9111(11) 0.9764(8) 0.6233(7) 0.029(3) Uani 1 d . B 2 H6A H 0.9030 1.0425 0.6033 0.035 Uiso 1 calc R B 2 H6B H 0.9028 0.9837 0.6817 0.035 Uiso 1 calc R B 2 C7 C 0.8077(11) 0.8955(9) 0.5722(7) 0.029(3) Uani 1 d . B 2 H7A H 0.8235 0.8280 0.5870 0.035 Uiso 1 calc R B 2 H7B H 0.7286 0.9096 0.5870 0.035 Uiso 1 calc R B 2 P16 P 0.8698(3) 0.7274(2) 0.40501(17) 0.0246(6) Uani 1 d . B 2 C15 C 0.7438(11) 0.7911(8) 0.4346(7) 0.029(3) Uani 1 d . B 2 H15A H 0.6841 0.7990 0.3854 0.035 Uiso 1 calc R B 2 H15B H 0.7015 0.7513 0.4701 0.035 Uiso 1 calc R B 2 C17 C 1.1493(11) 1.0197(8) 0.7579(6) 0.029(3) Uani 1 d . C 2 H17A H 1.1911 0.9613 0.7737 0.035 Uiso 1 calc R C 2 H17B H 1.0656 1.0099 0.7696 0.035 Uiso 1 calc R C 2 C18 C 1.2202(12) 1.1197(9) 0.8108(7) 0.031(3) Uani 1 d . C 2 O181 O 1.2703(9) 1.1874(6) 0.7800(5) 0.046(2) Uani 1 d . C 2 O182 O 1.2125(12) 1.1210(8) 0.8912(6) 0.069(3) Uani 1 d . C 2 O161 O 0.9377(8) 0.7849(6) 0.3505(5) 0.0310(19) Uani 1 d . B 2 O163 O 0.8124(7) 0.6184(5) 0.3572(4) 0.0287(18) Uani 1 d . B 2 O162 O 0.9532(7) 0.7132(6) 0.4895(5) 0.0278(17) Uani 1 d . B 2 C163 C 1.0870(11) 0.7064(9) 0.4951(8) 0.034(3) Uani 1 d . B 2 H16A H 1.1248 0.7035 0.5527 0.041 Uiso 1 calc R B 2 H16B H 1.1258 0.7676 0.4774 0.041 Uiso 1 calc R B 2 C164 C 1.1098(12) 0.6129(9) 0.4411(8) 0.039(3) Uani 1 d . B 2 H16C H 1.0600 0.5535 0.4519 0.046 Uiso 1 calc R B 2 H16D H 1.1962 0.6032 0.4536 0.046 Uiso 1 calc R B 2 H16E H 1.0876 0.6220 0.3832 0.046 Uiso 1 calc R B 2 C165 C 0.7680(11) 0.5342(9) 0.4008(7) 0.031(3) Uani 1 d . B 2 H16F H 0.7906 0.5544 0.4608 0.038 Uiso 1 calc R B 2 H16G H 0.8081 0.4738 0.3868 0.038 Uiso 1 calc R B 2 C166 C 0.6308(14) 0.5083(11) 0.3771(9) 0.051(4) Uani 1 d . B 2 H16H H 0.5912 0.5692 0.3871 0.061 Uiso 1 calc R B 2 H16I H 0.6034 0.4576 0.4100 0.061 Uiso 1 calc R B 2 H16J H 0.6091 0.4813 0.3188 0.061 Uiso 1 calc R B 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 I1 0.0467(5) 0.0291(4) 0.0429(5) 0.0033(3) -0.0022(4) 0.0021(4) I3 0.0414(5) 0.0502(5) 0.0420(5) -0.0046(4) 0.0120(4) 0.0037(4) I2 0.0465(5) 0.0292(4) 0.0281(4) -0.0006(3) 0.0082(3) 0.0050(4) I5 0.0405(5) 0.0343(4) 0.0499(5) -0.0132(4) 0.0165(4) -0.0067(4) I4 0.0332(5) 0.0494(5) 0.0620(6) 0.0001(4) 0.0048(4) 0.0015(4) I7 0.1004(10) 0.0374(5) 0.0748(7) 0.0000(5) 0.0463(7) 0.0063(5) I6 0.0800(8) 0.0446(5) 0.0440(5) -0.0096(4) 0.0251(5) -0.0202(5) N21 0.031(6) 0.021(5) 0.025(5) -0.008(4) -0.002(4) 0.002(4) C22 0.023(6) 0.025(6) 0.027(6) -0.008(4) 0.001(5) -0.001(5) C23 0.031(7) 0.030(6) 0.035(6) -0.005(5) 0.001(5) 0.009(5) N24 0.029(5) 0.029(5) 0.016(4) -0.005(4) -0.006(4) 0.002(4) C25 0.026(6) 0.023(6) 0.027(6) -0.005(4) 0.003(5) -0.003(5) C26 0.031(7) 0.024(6) 0.032(6) -0.012(5) 0.005(5) -0.004(5) C27 0.038(7) 0.018(5) 0.030(6) -0.011(4) 0.002(5) -0.003(5) C28 0.030(6) 0.039(7) 0.014(5) -0.004(4) 0.000(4) 0.006(5) C29 0.030(6) 0.034(6) 0.019(5) -0.008(5) 0.002(5) -0.003(5) C35 0.032(7) 0.027(6) 0.023(6) -0.006(4) -0.002(5) -0.006(5) P36 0.0333(17) 0.0225(14) 0.0273(15) -0.0026(12) 0.0056(13) -0.0006(13) O291 0.031(5) 0.038(5) 0.027(4) -0.007(3) 0.008(3) -0.007(4) O292 0.051(7) 0.067(7) 0.057(6) -0.020(5) 0.004(5) -0.008(6) O361 0.042(5) 0.017(4) 0.031(4) -0.009(3) 0.010(4) -0.003(3) O362 0.055(6) 0.021(4) 0.034(5) 0.000(3) 0.000(4) 0.009(4) O363 0.054(6) 0.033(5) 0.041(5) 0.002(4) 0.018(4) -0.009(4) C335 0.036(8) 0.054(9) 0.083(11) 0.018(8) 0.016(8) -0.002(7) C336 0.084(13) 0.038(8) 0.067(10) -0.010(7) 0.018(9) -0.029(8) C333 0.041(8) 0.042(8) 0.045(8) -0.002(6) -0.016(6) 0.017(6) C334 0.084(13) 0.048(9) 0.064(11) -0.005(8) 0.006(9) 0.004(9) N1 0.025(5) 0.015(4) 0.032(5) -0.009(4) 0.004(4) -0.005(4) C2 0.029(6) 0.016(5) 0.039(6) -0.007(5) 0.005(5) -0.001(5) C3 0.023(6) 0.025(6) 0.044(7) 0.001(5) -0.001(5) -0.002(5) N4 0.037(6) 0.018(4) 0.020(4) -0.007(3) 0.004(4) -0.006(4) C5 0.033(6) 0.015(5) 0.026(6) -0.009(4) 0.009(5) -0.009(5) C6 0.032(7) 0.025(6) 0.029(6) -0.001(5) 0.005(5) 0.000(5) C7 0.030(7) 0.026(6) 0.029(6) -0.003(5) 0.006(5) -0.005(5) P16 0.0332(17) 0.0160(13) 0.0216(14) -0.0051(10) 0.0035(12) -0.0011(12) C15 0.037(7) 0.020(5) 0.025(6) -0.011(4) 0.004(5) 0.000(5) C17 0.035(7) 0.026(6) 0.021(5) -0.009(4) 0.000(5) -0.004(5) C18 0.040(7) 0.024(6) 0.025(6) -0.002(5) 0.004(5) -0.003(5) O181 0.069(7) 0.027(4) 0.033(5) -0.005(4) 0.001(4) -0.019(4) O182 0.100(9) 0.052(6) 0.039(6) -0.012(5) 0.005(6) -0.029(6) O161 0.044(5) 0.020(4) 0.029(4) -0.006(3) 0.015(4) -0.001(4) O163 0.041(5) 0.014(4) 0.027(4) -0.006(3) 0.005(3) -0.005(3) O162 0.024(4) 0.029(4) 0.028(4) 0.000(3) 0.004(3) -0.002(3) C163 0.035(7) 0.023(6) 0.037(7) -0.010(5) 0.004(5) -0.012(5) C164 0.036(7) 0.029(6) 0.047(7) -0.010(5) 0.012(6) -0.004(6) C165 0.031(7) 0.029(6) 0.031(6) -0.005(5) 0.007(5) -0.004(5) C166 0.050(9) 0.047(8) 0.055(9) 0.003(7) 0.020(7) -0.010(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 I2 3.0102(13) . ? I3 I2 2.8309(13) . ? I5 I4 2.8434(14) . ? I5 I6 3.0371(15) . ? I7 I7 2.746(2) 2_675 ? N21 C22 1.444(14) . ? N21 C35 1.482(14) . ? N21 C27 1.488(14) . ? C22 C23 1.505(15) 2_667 ? C23 C22 1.505(15) 2_667 ? C23 N24 1.510(14) . ? N24 C28 1.505(13) . ? N24 C25 1.526(14) . ? C25 C26 1.483(15) . ? C26 C27 1.521(16) . ? C28 C29 1.499(16) . ? C29 O291 1.232(12) . ? C29 O292 1.346(14) . ? C35 P36 1.801(11) . ? P36 O361 1.494(8) . ? P36 O362 1.545(9) . ? P36 O363 1.565(9) . ? O362 C333 1.451(15) . ? O363 C335 1.455(18) . ? C335 C336 1.485(19) . ? C333 C334 1.50(2) . ? N1 C2 1.466(15) . ? N1 C7 1.479(14) . ? N1 C15 1.492(12) . ? C2 C3 1.516(16) . ? C3 N4 1.529(15) 2_776 ? N4 C17 1.483(13) . ? N4 C3 1.529(15) 2_776 ? N4 C5 1.536(13) . ? C5 C6 1.518(16) . ? C6 C7 1.539(15) . ? P16 O161 1.481(8) . ? P16 O162 1.562(8) . ? P16 O163 1.573(7) . ? P16 C15 1.794(12) . ? C17 C18 1.551(15) . ? C18 O181 1.205(14) . ? C18 O182 1.331(15) . ? O163 C165 1.472(13) . ? O162 C163 1.469(14) . ? C163 C164 1.501(15) . ? C165 C166 1.487(18) . ? 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 I3 I2 I1 176.27(4) . . ? I4 I5 I6 176.69(4) . . ? C22 N21 C35 114.8(9) . . ? C22 N21 C27 112.3(8) . . ? C35 N21 C27 110.5(9) . . ? N21 C22 C23 114.5(9) . 2_667 ? C22 C23 N24 113.8(10) 2_667 . ? C28 N24 C23 111.7(9) . . ? C28 N24 C25 111.7(8) . . ? C23 N24 C25 111.6(8) . . ? C26 C25 N24 112.8(9) . . ? C25 C26 C27 110.9(9) . . ? N21 C27 C26 113.5(9) . . ? C29 C28 N24 112.5(8) . . ? O291 C29 O292 122.9(10) . . ? O291 C29 C28 123.2(9) . . ? O292 C29 C28 113.9(9) . . ? N21 C35 P36 107.5(8) . . ? O361 P36 O362 114.9(5) . . ? O361 P36 O363 113.1(5) . . ? O362 P36 O363 103.3(5) . . ? O361 P36 C35 111.8(5) . . ? O362 P36 C35 104.2(5) . . ? O363 P36 C35 108.9(5) . . ? C333 O362 P36 119.9(7) . . ? C335 O363 P36 124.9(8) . . ? O363 C335 C336 108.4(13) . . ? O362 C333 C334 110.3(11) . . ? C2 N1 C7 111.2(8) . . ? C2 N1 C15 112.2(9) . . ? C7 N1 C15 111.5(8) . . ? N1 C2 C3 114.7(9) . . ? C2 C3 N4 114.0(9) . 2_776 ? C17 N4 C3 112.0(9) . 2_776 ? C17 N4 C5 110.7(8) . . ? C3 N4 C5 111.1(8) 2_776 . ? C6 C5 N4 111.1(8) . . ? C5 C6 C7 110.4(9) . . ? N1 C7 C6 112.9(9) . . ? O161 P16 O162 113.3(5) . . ? O161 P16 O163 109.6(4) . . ? O162 P16 O163 109.0(4) . . ? O161 P16 C15 112.6(5) . . ? O162 P16 C15 104.9(5) . . ? O163 P16 C15 107.2(5) . . ? N1 C15 P16 107.1(8) . . ? N4 C17 C18 111.4(9) . . ? O181 C18 O182 126.3(10) . . ? O181 C18 C17 122.4(10) . . ? O182 C18 C17 111.2(10) . . ? C165 O163 P16 122.2(6) . . ? C163 O162 P16 120.8(7) . . ? O162 C163 C164 111.2(9) . . ? O163 C165 C166 111.2(10) . . ? 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 C35 N21 C22 C23 62.6(12) . . . 2_667 ? C27 N21 C22 C23 -170.0(9) . . . 2_667 ? C22 C23 N24 C28 167.4(9) 2_667 . . . ? C22 C23 N24 C25 -66.7(12) 2_667 . . . ? C28 N24 C25 C26 -63.8(13) . . . . ? C23 N24 C25 C26 170.3(10) . . . . ? N24 C25 C26 C27 -177.0(9) . . . . ? C22 N21 C27 C26 75.7(12) . . . . ? C35 N21 C27 C26 -154.7(9) . . . . ? C25 C26 C27 N21 67.4(13) . . . . ? C23 N24 C28 C29 -73.8(12) . . . . ? C25 N24 C28 C29 160.4(9) . . . . ? N24 C28 C29 O291 26.1(17) . . . . ? N24 C28 C29 O292 -156.0(11) . . . . ? C22 N21 C35 P36 -133.2(8) . . . . ? C27 N21 C35 P36 98.5(9) . . . . ? N21 C35 P36 O361 55.1(9) . . . . ? N21 C35 P36 O362 -69.5(8) . . . . ? N21 C35 P36 O363 -179.3(7) . . . . ? O361 P36 O362 C333 62.0(10) . . . . ? O363 P36 O362 C333 -61.6(10) . . . . ? C35 P36 O362 C333 -175.4(10) . . . . ? O361 P36 O363 C335 32.8(12) . . . . ? O362 P36 O363 C335 157.6(11) . . . . ? C35 P36 O363 C335 -92.1(11) . . . . ? P36 O363 C335 C336 -155.2(10) . . . . ? P36 O362 C333 C334 128.7(11) . . . . ? C7 N1 C2 C3 172.2(9) . . . . ? C15 N1 C2 C3 -62.1(12) . . . . ? N1 C2 C3 N4 -39.5(12) . . . 2_776 ? C17 N4 C5 C6 71.3(12) . . . . ? C3 N4 C5 C6 -163.7(9) 2_776 . . . ? N4 C5 C6 C7 -179.3(9) . . . . ? C2 N1 C7 C6 -79.6(12) . . . . ? C15 N1 C7 C6 154.3(10) . . . . ? C5 C6 C7 N1 -70.3(12) . . . . ? C2 N1 C15 P16 131.7(8) . . . . ? C7 N1 C15 P16 -102.8(9) . . . . ? O161 P16 C15 N1 -60.0(9) . . . . ? O162 P16 C15 N1 63.6(8) . . . . ? O163 P16 C15 N1 179.4(7) . . . . ? C3 N4 C17 C18 74.7(12) 2_776 . . . ? C5 N4 C17 C18 -160.8(10) . . . . ? N4 C17 C18 O181 -5.0(17) . . . . ? N4 C17 C18 O182 172.2(11) . . . . ? O161 P16 O163 C165 163.9(8) . . . . ? O162 P16 O163 C165 39.3(9) . . . . ? C15 P16 O163 C165 -73.6(9) . . . . ? O161 P16 O162 C163 -30.1(9) . . . . ? O163 P16 O162 C163 92.2(8) . . . . ? C15 P16 O162 C163 -153.3(8) . . . . ? P16 O162 C163 C164 -63.7(12) . . . . ? P16 O163 C165 C166 113.2(10) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.57 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 2.285 _refine_diff_density_min -2.091 _refine_diff_density_rms 0.268 #==END data_compound_4 _database_code_depnum_ccdc_archive 'CCDC 689803' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H43.50 Cl2 N4 O21.25 P' _chemical_formula_weight 745.93 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' P P 0.1023 0.0942 '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 Orthorhombic _symmetry_space_group_name_H-M Pca21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 11.6204(4) _cell_length_b 12.5139(4) _cell_length_c 20.6339(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3000.51(17) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block-shaped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.651 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1570 _exptl_absorpt_coefficient_mu 0.368 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9642 _exptl_absorpt_correction_T_max 0.9854 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15170 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0668 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 29.13 _reflns_number_total 7743 _reflns_number_gt 5421 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0796P)^2^+1.6283P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(10) _refine_ls_number_reflns 7743 _refine_ls_number_parameters 425 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0931 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.1548 _refine_ls_wR_factor_gt 0.1293 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl Cl 0.13776(8) 0.43094(7) 0.36578(5) 0.0232(2) Uani 1 d . . . O11 O 0.2076(3) 0.5246(3) 0.37464(18) 0.0414(9) Uani 1 d . . . O12 O 0.2072(3) 0.3411(3) 0.35237(18) 0.0409(9) Uani 1 d . . . O13 O 0.0644(4) 0.4489(3) 0.3101(2) 0.0611(12) Uani 1 d . . . O14 O 0.0683(5) 0.4124(3) 0.4208(2) 0.0675(14) Uani 1 d . . . Cl2 Cl 0.13568(9) 0.06423(8) 0.39908(6) 0.0317(3) Uani 1 d . . . O21 O 0.0633(3) 0.1483(3) 0.4194(2) 0.0474(10) Uani 1 d . . . O22 O 0.0801(3) -0.0363(3) 0.40711(19) 0.0409(9) Uani 1 d . . . O23 O 0.1574(4) 0.0781(3) 0.3300(2) 0.0628(13) Uani 1 d . . . O24 O 0.2439(4) 0.0645(3) 0.4299(3) 0.0747(16) Uani 1 d . . . N1 N 0.0287(3) 0.3172(2) 0.00394(14) 0.0146(6) Uani 1 d . . . H1 H 0.0523 0.2795 0.0404 0.018 Uiso 1 calc R . . C2 C -0.0991(3) 0.3313(3) 0.00979(18) 0.0172(8) Uani 1 d . . . H2A H -0.1295 0.3625 -0.0308 0.021 Uiso 1 calc R . . H2B H -0.1160 0.3817 0.0455 0.021 Uiso 1 calc R . . C3 C -0.1593(3) 0.2250(3) 0.02295(18) 0.0197(8) Uani 1 d . . . H3A H -0.1330 0.1714 -0.0091 0.024 Uiso 1 calc R . . H3B H -0.1376 0.1991 0.0666 0.024 Uiso 1 calc R . . N4 N -0.2875(3) 0.2353(2) 0.01911(15) 0.0192(7) Uani 1 d . . . H4 H -0.3099 0.2819 0.0519 0.023 Uiso 1 calc R . . C5 C -0.3327(3) 0.2801(3) -0.04353(18) 0.0189(8) Uani 1 d . . . H5A H -0.3052 0.3546 -0.0485 0.023 Uiso 1 calc R . . H5B H -0.4178 0.2816 -0.0420 0.023 Uiso 1 calc R . . C6 C -0.2944(4) 0.2150(3) -0.10167(19) 0.0215(8) Uani 1 d . . . H6A H -0.2093 0.2135 -0.1035 0.026 Uiso 1 calc R . . H6B H -0.3220 0.1406 -0.0970 0.026 Uiso 1 calc R . . C7 C -0.3412(3) 0.2622(3) -0.16403(18) 0.0214(8) Uani 1 d . . . H7A H -0.3108 0.3355 -0.1696 0.026 Uiso 1 calc R . . H7B H -0.4261 0.2667 -0.1613 0.026 Uiso 1 calc R . . N8 N -0.3078(3) 0.1948(2) -0.22217(15) 0.0192(7) Uani 1 d . . . H8 H -0.3337 0.2304 -0.2589 0.023 Uiso 1 calc R . . C9 C -0.1813(3) 0.1792(3) -0.22989(19) 0.0208(8) Uani 1 d . . . H9A H -0.1668 0.1318 -0.2674 0.025 Uiso 1 calc R . . H9B H -0.1504 0.1437 -0.1907 0.025 Uiso 1 calc R . . C10 C -0.1188(4) 0.2849(3) -0.24018(19) 0.0223(8) Uani 1 d . . . H10A H -0.1424 0.3161 -0.2822 0.027 Uiso 1 calc R . . H10B H -0.1407 0.3356 -0.2055 0.027 Uiso 1 calc R . . N11 N 0.0093(3) 0.2689(3) -0.23959(15) 0.0221(7) Uani 1 d . . . H11 H 0.0255 0.2173 -0.2707 0.027 Uiso 1 calc R . . C12 C 0.0583(4) 0.2280(3) -0.17553(18) 0.0203(8) Uani 1 d . . . H12A H 0.1429 0.2208 -0.1795 0.024 Uiso 1 calc R . . H12B H 0.0262 0.1563 -0.1663 0.024 Uiso 1 calc R . . C13 C 0.0301(4) 0.3039(3) -0.11850(17) 0.0218(8) Uani 1 d . . . H13A H 0.0708 0.3726 -0.1245 0.026 Uiso 1 calc R . . H13B H -0.0536 0.3185 -0.1176 0.026 Uiso 1 calc R . . C14 C 0.0671(3) 0.2530(3) -0.05448(17) 0.0190(8) Uani 1 d . . . H14A H 0.0342 0.1801 -0.0516 0.023 Uiso 1 calc R . . H14B H 0.1519 0.2463 -0.0538 0.023 Uiso 1 calc R . . C15 C 0.0906(3) 0.4231(3) 0.00558(18) 0.0181(8) Uani 1 d . . . H15A H 0.0612 0.4679 -0.0304 0.022 Uiso 1 calc R . . H15B H 0.1734 0.4101 -0.0026 0.022 Uiso 1 calc R . . P16 P 0.07640(9) 0.49828(9) 0.08113(5) 0.0207(2) Uani 1 d . . . O161 O -0.0485(2) 0.5490(2) 0.08290(16) 0.0275(6) Uani 1 d . . . O162 O 0.0774(3) 0.4167(2) 0.13457(15) 0.0263(7) Uani 1 d . . . O163 O 0.1698(2) 0.5772(2) 0.07958(15) 0.0239(6) Uani 1 d . . . C17 C -0.3404(4) 0.1277(3) 0.0343(2) 0.0271(9) Uani 1 d . . . H17A H -0.3880 0.1044 -0.0028 0.032 Uiso 1 calc R . . H17B H -0.2783 0.0745 0.0404 0.032 Uiso 1 calc R . . C18 C -0.4131(4) 0.1315(3) 0.09378(19) 0.0262(9) Uani 1 d . . . O181 O -0.4589(5) 0.0400(3) 0.1054(2) 0.0721(17) Uani 1 d . . . O182 O -0.4229(3) 0.2124(2) 0.12571(14) 0.0346(8) Uani 1 d . . . C19 C -0.3672(4) 0.0878(3) -0.2205(2) 0.0250(9) Uani 1 d . . . H19A H -0.4437 0.0958 -0.2000 0.030 Uiso 1 calc R . . H19B H -0.3215 0.0376 -0.1939 0.030 Uiso 1 calc R . . C20 C -0.3818(4) 0.0420(3) -0.2885(2) 0.0263(9) Uani 1 d . . . O201 O -0.4485(3) -0.0398(3) -0.28876(16) 0.0409(9) Uani 1 d . . . O202 O -0.3399(4) 0.0869(3) -0.33503(16) 0.0444(9) Uani 1 d . . . C21 C 0.0683(4) 0.3702(3) -0.2612(2) 0.0252(9) Uani 1 d . . . H21A H 0.0802 0.4175 -0.2233 0.030 Uiso 1 calc R . . H21B H 0.0187 0.4083 -0.2926 0.030 Uiso 1 calc R . . C22 C 0.1828(4) 0.3456(4) -0.2922(2) 0.0290(10) Uani 1 d . . . O221 O 0.2443(3) 0.4317(2) -0.29962(14) 0.0304(7) Uani 1 d . . . O222 O 0.2085(3) 0.2565(3) -0.30844(18) 0.0445(9) Uani 1 d . . . O300 O 0.0552(5) 0.2285(5) 0.2328(3) 0.0965(19) Uani 1 d . . . O400 O 0.3560(4) 0.2816(3) 0.0308(2) 0.0645(12) Uani 1 d . . . O500 O 0.0868(7) 0.1754(13) 0.0986(8) 0.031(3) Uani 0.50 d P A 1 O600 O 0.1296(9) 0.1808(11) 0.0920(8) 0.034(3) Uani 0.50 d P B 2 O700 O 0.8592(3) 0.3467(3) 0.18110(18) 0.0426(9) Uani 1 d . . . O800 O -0.1925(11) -0.0895(10) 0.0741(7) 0.036(3) Uani 0.25 d P . . 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 Cl 0.0225(5) 0.0140(4) 0.0332(5) 0.0002(4) 0.0036(4) 0.0001(4) O11 0.043(2) 0.0265(17) 0.054(2) -0.0041(16) -0.0043(17) -0.0138(15) O12 0.0373(18) 0.0236(17) 0.062(2) -0.0054(16) 0.0072(18) 0.0154(14) O13 0.053(3) 0.053(3) 0.077(3) 0.003(2) -0.035(2) 0.007(2) O14 0.096(4) 0.038(2) 0.068(3) 0.002(2) 0.054(3) -0.002(2) Cl2 0.0226(5) 0.0149(5) 0.0575(7) -0.0023(5) -0.0048(5) 0.0013(4) O21 0.045(2) 0.0273(18) 0.070(3) 0.0000(18) 0.0114(19) 0.0129(16) O22 0.046(2) 0.0208(16) 0.055(2) 0.0024(16) -0.0016(18) -0.0135(15) O23 0.080(3) 0.046(3) 0.062(3) 0.011(2) 0.030(3) 0.012(2) O24 0.037(2) 0.043(2) 0.144(5) -0.008(3) -0.044(3) 0.0009(19) N1 0.0185(15) 0.0130(14) 0.0123(14) -0.0021(12) -0.0026(12) 0.0001(12) C2 0.0172(18) 0.0175(18) 0.0170(17) -0.0007(14) 0.0001(14) -0.0023(15) C3 0.027(2) 0.0164(18) 0.0155(17) 0.0026(15) 0.0025(16) -0.0039(16) N4 0.0244(17) 0.0158(15) 0.0175(15) -0.0050(13) 0.0069(13) -0.0042(13) C5 0.0187(18) 0.0180(18) 0.0201(18) -0.0038(15) 0.0000(16) 0.0013(15) C6 0.027(2) 0.0190(18) 0.0187(18) -0.0037(15) -0.0014(17) 0.0043(16) C7 0.0191(19) 0.021(2) 0.024(2) -0.0037(16) -0.0032(16) -0.0043(16) N8 0.0270(17) 0.0138(15) 0.0167(15) 0.0017(12) -0.0060(14) -0.0024(14) C9 0.026(2) 0.0183(19) 0.0186(19) -0.0001(15) -0.0029(16) -0.0002(16) C10 0.029(2) 0.0218(19) 0.0164(18) -0.0020(16) -0.0054(16) 0.0032(18) N11 0.0276(18) 0.0236(18) 0.0151(15) -0.0053(14) 0.0027(14) -0.0046(15) C12 0.027(2) 0.0182(19) 0.0160(17) -0.0013(15) 0.0036(16) -0.0009(16) C13 0.030(2) 0.0201(19) 0.0152(18) -0.0033(14) 0.0011(15) 0.0063(17) C14 0.0206(19) 0.0178(18) 0.0186(18) 0.0002(15) 0.0014(16) 0.0000(15) C15 0.0223(19) 0.0143(17) 0.0177(17) 0.0013(14) 0.0009(15) -0.0028(15) P16 0.0241(5) 0.0185(4) 0.0195(4) 0.0011(4) -0.0010(4) -0.0018(4) O161 0.0271(15) 0.0262(15) 0.0293(14) -0.0033(14) 0.0000(13) 0.0009(12) O162 0.0287(16) 0.0208(15) 0.0295(15) 0.0070(12) -0.0071(13) -0.0047(13) O163 0.0231(13) 0.0218(14) 0.0267(14) 0.0044(13) 0.0003(13) -0.0029(12) C17 0.035(2) 0.0174(19) 0.029(2) -0.0066(17) 0.0117(19) -0.0090(17) C18 0.039(2) 0.023(2) 0.017(2) -0.0017(16) 0.0081(18) -0.0071(18) O181 0.131(4) 0.0229(18) 0.063(3) -0.0144(17) 0.070(3) -0.032(2) O182 0.058(2) 0.0226(15) 0.0229(15) -0.0049(13) 0.0146(16) -0.0076(16) C19 0.032(2) 0.0188(19) 0.024(2) -0.0007(16) -0.0068(18) -0.0084(18) C20 0.034(2) 0.022(2) 0.023(2) 0.0015(18) -0.0112(19) -0.0056(18) O201 0.063(2) 0.0262(17) 0.0339(18) -0.0039(14) -0.0199(17) -0.0126(16) O202 0.068(3) 0.044(2) 0.0215(16) -0.0034(15) -0.0053(17) -0.0152(19) C21 0.030(2) 0.025(2) 0.0203(19) 0.0025(16) 0.0087(17) -0.0079(18) C22 0.033(2) 0.034(2) 0.0200(19) 0.0036(18) 0.0055(18) -0.005(2) O221 0.0345(16) 0.0284(16) 0.0283(16) 0.0046(13) 0.0099(14) -0.0030(14) O222 0.050(2) 0.0342(19) 0.049(2) -0.0059(17) 0.0235(18) -0.0004(17) O300 0.077(4) 0.112(5) 0.101(4) 0.008(4) 0.013(3) 0.002(3) O400 0.078(3) 0.048(2) 0.067(3) -0.010(2) -0.013(3) -0.011(2) O500 0.022(5) 0.038(5) 0.033(5) 0.019(3) -0.001(5) 0.005(5) O600 0.043(7) 0.021(4) 0.038(6) 0.005(4) -0.012(6) 0.002(6) O700 0.044(2) 0.0334(19) 0.050(2) 0.0225(16) 0.0175(18) 0.0071(16) O800 0.031(7) 0.037(7) 0.041(8) -0.015(6) -0.001(6) 0.009(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 Cl O12 1.412(3) . ? Cl O14 1.412(4) . ? Cl O11 1.437(3) . ? Cl O13 1.448(4) . ? Cl2 O24 1.409(4) . ? Cl2 O21 1.411(4) . ? Cl2 O22 1.424(3) . ? Cl2 O23 1.459(4) . ? N1 C2 1.500(5) . ? N1 C15 1.508(5) . ? N1 C14 1.516(5) . ? N1 H1 0.9300 . ? C2 C3 1.527(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N4 1.498(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N4 C5 1.504(5) . ? N4 C17 1.512(5) . ? N4 H4 0.9300 . ? C5 C6 1.517(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.516(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N8 1.517(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? N8 C9 1.490(5) . ? N8 C19 1.506(5) . ? N8 H8 0.9300 . ? C9 C10 1.524(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N11 1.502(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? N11 C21 1.508(5) . ? N11 C12 1.528(5) . ? N11 H11 0.9300 . ? C12 C13 1.547(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.528(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 P16 1.828(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? P16 O163 1.467(3) . ? P16 O162 1.503(3) . ? P16 O161 1.585(3) . ? C17 C18 1.491(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 O182 1.213(5) . ? C18 O181 1.286(5) . ? C19 C20 1.526(6) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 O202 1.214(5) . ? C20 O201 1.284(5) . ? C21 C22 1.509(6) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 O222 1.202(5) . ? C22 O221 1.301(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 O12 Cl O14 110.7(2) . . ? O12 Cl O11 110.6(2) . . ? O14 Cl O11 110.8(3) . . ? O12 Cl O13 107.8(2) . . ? O14 Cl O13 109.1(3) . . ? O11 Cl O13 107.9(2) . . ? O24 Cl2 O21 113.4(3) . . ? O24 Cl2 O22 110.7(3) . . ? O21 Cl2 O22 110.7(2) . . ? O24 Cl2 O23 106.6(3) . . ? O21 Cl2 O23 107.8(3) . . ? O22 Cl2 O23 107.3(3) . . ? C2 N1 C15 111.6(3) . . ? C2 N1 C14 114.7(3) . . ? C15 N1 C14 110.1(3) . . ? C2 N1 H1 106.7 . . ? C15 N1 H1 106.7 . . ? C14 N1 H1 106.7 . . ? N1 C2 C3 111.4(3) . . ? N1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? N1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? N4 C3 C2 111.8(3) . . ? N4 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? N4 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 107.9 . . ? C3 N4 C5 115.1(3) . . ? C3 N4 C17 108.4(3) . . ? C5 N4 C17 111.6(3) . . ? C3 N4 H4 107.1 . . ? C5 N4 H4 107.1 . . ? C17 N4 H4 107.1 . . ? N4 C5 C6 112.2(3) . . ? N4 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? N4 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C5 110.9(3) . . ? C7 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.0 . . ? C6 C7 N8 111.3(3) . . ? C6 C7 H7A 109.4 . . ? N8 C7 H7A 109.4 . . ? C6 C7 H7B 109.4 . . ? N8 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C9 N8 C19 109.7(3) . . ? C9 N8 C7 114.2(3) . . ? C19 N8 C7 111.0(3) . . ? C9 N8 H8 107.2 . . ? C19 N8 H8 107.2 . . ? C7 N8 H8 107.2 . . ? N8 C9 C10 111.8(3) . . ? N8 C9 H9A 109.3 . . ? C10 C9 H9A 109.3 . . ? N8 C9 H9B 109.3 . . ? C10 C9 H9B 109.3 . . ? H9A C9 H9B 107.9 . . ? N11 C10 C9 110.9(3) . . ? N11 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? N11 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C10 N11 C21 109.7(3) . . ? C10 N11 C12 114.9(3) . . ? C21 N11 C12 111.5(3) . . ? C10 N11 H11 106.7 . . ? C21 N11 H11 106.7 . . ? C12 N11 H11 106.7 . . ? N11 C12 C13 111.9(3) . . ? N11 C12 H12A 109.2 . . ? C13 C12 H12A 109.2 . . ? N11 C12 H12B 109.2 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C14 C13 C12 110.0(3) . . ? C14 C13 H13A 109.7 . . ? C12 C13 H13A 109.7 . . ? C14 C13 H13B 109.7 . . ? C12 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? N1 C14 C13 112.6(3) . . ? N1 C14 H14A 109.1 . . ? C13 C14 H14A 109.1 . . ? N1 C14 H14B 109.1 . . ? C13 C14 H14B 109.1 . . ? H14A C14 H14B 107.8 . . ? N1 C15 P16 115.4(2) . . ? N1 C15 H15A 108.4 . . ? P16 C15 H15A 108.4 . . ? N1 C15 H15B 108.4 . . ? P16 C15 H15B 108.4 . . ? H15A C15 H15B 107.5 . . ? O163 P16 O162 117.85(17) . . ? O163 P16 O161 114.08(17) . . ? O162 P16 O161 105.23(18) . . ? O163 P16 C15 105.14(18) . . ? O162 P16 C15 105.98(18) . . ? O161 P16 C15 107.96(18) . . ? C18 C17 N4 111.9(3) . . ? C18 C17 H17A 109.2 . . ? N4 C17 H17A 109.2 . . ? C18 C17 H17B 109.2 . . ? N4 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? O182 C18 O181 127.2(4) . . ? O182 C18 C17 121.8(4) . . ? O181 C18 C17 111.1(4) . . ? N8 C19 C20 111.3(3) . . ? N8 C19 H19A 109.4 . . ? C20 C19 H19A 109.4 . . ? N8 C19 H19B 109.4 . . ? C20 C19 H19B 109.4 . . ? H19A C19 H19B 108.0 . . ? O202 C20 O201 127.4(4) . . ? O202 C20 C19 120.6(4) . . ? O201 C20 C19 111.7(4) . . ? N11 C21 C22 110.8(4) . . ? N11 C21 H21A 109.5 . . ? C22 C21 H21A 109.5 . . ? N11 C21 H21B 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 108.1 . . ? O222 C22 O221 126.7(4) . . ? O222 C22 C21 121.8(4) . . ? O221 C22 C21 111.4(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N1 C2 C3 -167.6(3) . . . . ? C14 N1 C2 C3 66.4(4) . . . . ? N1 C2 C3 N4 -171.6(3) . . . . ? C2 C3 N4 C5 55.5(4) . . . . ? C2 C3 N4 C17 -178.6(3) . . . . ? C3 N4 C5 C6 57.0(4) . . . . ? C17 N4 C5 C6 -67.1(4) . . . . ? N4 C5 C6 C7 -180.0(3) . . . . ? C5 C6 C7 N8 -177.5(3) . . . . ? C6 C7 N8 C9 -57.0(4) . . . . ? C6 C7 N8 C19 67.6(4) . . . . ? C19 N8 C9 C10 173.0(3) . . . . ? C7 N8 C9 C10 -61.7(4) . . . . ? N8 C9 C10 N11 173.0(3) . . . . ? C9 C10 N11 C21 170.3(3) . . . . ? C9 C10 N11 C12 -63.1(4) . . . . ? C10 N11 C12 C13 -58.3(4) . . . . ? C21 N11 C12 C13 67.4(4) . . . . ? N11 C12 C13 C14 172.7(3) . . . . ? C2 N1 C14 C13 60.2(4) . . . . ? C15 N1 C14 C13 -66.6(4) . . . . ? C12 C13 C14 N1 -173.0(3) . . . . ? C2 N1 C15 P16 63.5(3) . . . . ? C14 N1 C15 P16 -168.1(3) . . . . ? N1 C15 P16 O163 162.4(3) . . . . ? N1 C15 P16 O162 36.9(3) . . . . ? N1 C15 P16 O161 -75.4(3) . . . . ? C3 N4 C17 C18 117.4(4) . . . . ? C5 N4 C17 C18 -114.7(4) . . . . ? N4 C17 C18 O182 -2.3(7) . . . . ? N4 C17 C18 O181 178.9(4) . . . . ? C9 N8 C19 C20 -79.4(4) . . . . ? C7 N8 C19 C20 153.4(3) . . . . ? N8 C19 C20 O202 5.5(6) . . . . ? N8 C19 C20 O201 -169.3(4) . . . . ? C10 N11 C21 C22 -152.1(3) . . . . ? C12 N11 C21 C22 79.4(4) . . . . ? N11 C21 C22 O222 13.9(6) . . . . ? N11 C21 C22 O221 -167.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.559 _refine_diff_density_min -0.557 _refine_diff_density_rms 0.090 #==END data_compound_5 _database_code_depnum_ccdc_archive 'CCDC 689804' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H37 Cl2 Cu2 N4 O13' _chemical_formula_weight 691.48 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.9690(5) _cell_length_b 19.5142(10) _cell_length_c 15.7711(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.118(3) _cell_angle_gamma 90.00 _cell_volume 2756.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block shaped' _exptl_crystal_colour blue _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.666 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1428 _exptl_absorpt_coefficient_mu 1.803 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8692 _exptl_absorpt_correction_T_max 0.9648 _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24319 _diffrn_reflns_av_R_equivalents 0.0695 _diffrn_reflns_av_sigmaI/netI 0.0706 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 26.40 _reflns_number_total 5234 _reflns_number_gt 4037 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0595P)^2^+21.9850P] 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 5234 _refine_ls_number_parameters 380 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.0901 _refine_ls_R_factor_gt 0.0651 _refine_ls_wR_factor_ref 0.1712 _refine_ls_wR_factor_gt 0.1598 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu2 Cu 0.29997(8) 0.09175(4) 0.94419(5) 0.0169(2) Uani 1 d . . . Cl1 Cl 0.53764(16) 0.12928(9) 0.94210(11) 0.0268(4) Uani 1 d . . . O1 O 0.2497(5) 0.1613(2) 1.0261(3) 0.0194(10) Uani 1 d D . . HA H 0.209(6) 0.1983(15) 1.014(4) 0.023 Uiso 1 d D . . HB H 0.305(6) 0.168(3) 1.069(3) 0.023 Uiso 1 d D . . O2 O 0.2660(5) 0.0105(2) 1.0480(3) 0.0225(10) Uani 1 d D . . HC H 0.292(7) 0.026(3) 1.095(2) 0.027 Uiso 1 d D . . HD H 0.325(6) -0.021(3) 1.038(4) 0.027 Uiso 1 d D . . O3 O 0.3332(6) 0.0155(3) 0.8674(4) 0.0371(13) Uani 1 d D . . HE H 0.360(8) 0.026(4) 0.821(2) 0.045 Uiso 1 d D . . HF H 0.265(7) -0.013(3) 0.863(4) 0.045 Uiso 1 d D . . Cu1 Cu 0.04761(8) 0.24129(4) 0.73296(5) 0.0145(2) Uani 1 d . . . N1 N -0.1472(5) 0.2001(3) 0.7807(3) 0.0189(12) Uani 1 d . . . C2 C -0.1947(7) 0.2542(4) 0.8401(4) 0.0227(15) Uani 1 d . . . H2A H -0.2678 0.2350 0.8785 0.027 Uiso 1 calc R . . H2B H -0.2434 0.2922 0.8075 0.027 Uiso 1 calc R . . C3 C -0.0601(7) 0.2808(4) 0.8915(4) 0.0247(15) Uani 1 d . . . H3A H -0.0914 0.3171 0.9307 0.030 Uiso 1 calc R . . H3B H -0.0144 0.2432 0.9260 0.030 Uiso 1 calc R . . N4 N 0.0516(6) 0.3091(3) 0.8345(3) 0.0192(12) Uani 1 d . . . C5 C 0.1979(7) 0.3127(4) 0.8830(4) 0.0262(15) Uani 1 d . . . H5A H 0.2171 0.2680 0.9112 0.031 Uiso 1 calc R . . H5B H 0.1915 0.3477 0.9280 0.031 Uiso 1 calc R . . C6 C 0.3309(7) 0.3299(4) 0.8300(4) 0.0273(16) Uani 1 d . . . H6A H 0.3100 0.3737 0.7999 0.033 Uiso 1 calc R . . H6B H 0.4198 0.3371 0.8690 0.033 Uiso 1 calc R . . C7 C 0.3679(7) 0.2759(4) 0.7651(4) 0.0232(15) Uani 1 d . . . H7A H 0.4663 0.2869 0.7430 0.028 Uiso 1 calc R . . H7B H 0.3768 0.2310 0.7940 0.028 Uiso 1 calc R . . N8 N 0.2548(5) 0.2700(3) 0.6916(3) 0.0170(11) Uani 1 d . . . C9 C 0.2940(7) 0.2110(4) 0.6372(5) 0.0272(16) Uani 1 d . . . H9A H 0.3251 0.1715 0.6735 0.033 Uiso 1 calc R . . H9B H 0.3785 0.2236 0.6025 0.033 Uiso 1 calc R . . C10 C 0.1602(8) 0.1914(4) 0.5799(4) 0.0287(16) Uani 1 d . . . H10A H 0.1316 0.2298 0.5414 0.034 Uiso 1 calc R . . H10B H 0.1839 0.1510 0.5450 0.034 Uiso 1 calc R . . N11 N 0.0364(6) 0.1750(3) 0.6352(3) 0.0224(12) Uani 1 d . . . H11 H 0.0569 0.1319 0.6581 0.027 Uiso 1 calc R . . C12 C -0.1083(8) 0.1692(4) 0.5862(4) 0.0295(16) Uani 1 d . . . H12A H -0.0976 0.1377 0.5378 0.035 Uiso 1 calc R . . H12B H -0.1376 0.2148 0.5632 0.035 Uiso 1 calc R . . C13 C -0.2298(8) 0.1426(4) 0.6416(5) 0.0312(17) Uani 1 d . . . H13A H -0.3211 0.1345 0.6048 0.037 Uiso 1 calc R . . H13B H -0.1973 0.0979 0.6655 0.037 Uiso 1 calc R . . C14 C -0.2700(7) 0.1888(4) 0.7140(4) 0.0277(16) Uani 1 d . . . H14A H -0.3015 0.2338 0.6903 0.033 Uiso 1 calc R . . H14B H -0.3567 0.1687 0.7413 0.033 Uiso 1 calc R . . C15 C -0.1130(7) 0.1354(4) 0.8278(4) 0.0230(15) Uani 1 d . . . H15A H -0.1430 0.0961 0.7911 0.028 Uiso 1 calc R . . H15B H -0.1733 0.1338 0.8785 0.028 Uiso 1 calc R . . C16 C 0.0508(6) 0.1279(3) 0.8560(4) 0.0145(13) Uani 1 d . . . C19 C 0.2456(7) 0.3345(3) 0.6430(4) 0.0241(15) Uani 1 d . . . H19A H 0.2025 0.3697 0.6798 0.029 Uiso 1 calc R . . H19B H 0.1733 0.3274 0.5942 0.029 Uiso 1 calc R . . C18 C -0.0832(8) 0.3815(4) 0.7202(5) 0.0328(18) Uani 1 d . . . C17 C 0.0031(8) 0.3788(4) 0.8058(4) 0.0272(16) Uani 1 d . . . H17A H 0.0928 0.4081 0.8030 0.033 Uiso 1 calc R . . H17B H -0.0600 0.3986 0.8491 0.033 Uiso 1 calc R . . O181 O -0.0895(5) 0.3298(2) 0.6737(3) 0.0223(10) Uani 1 d . . . O182 O -0.1420(10) 0.4382(3) 0.7029(4) 0.081(3) Uani 1 d . . . C20 C 0.3895(7) 0.3651(4) 0.6081(4) 0.0253(16) Uani 1 d . . . O201 O 0.4860(6) 0.3241(3) 0.5850(4) 0.0416(14) Uani 1 d . . . O202 O 0.3940(5) 0.4276(3) 0.6040(3) 0.0334(12) Uani 1 d . . . O161 O 0.0792(4) 0.0844(2) 0.9146(3) 0.0171(9) Uani 1 d . . . O162 O 0.1488(4) 0.1609(2) 0.8214(3) 0.0202(10) Uani 1 d . . . Cl2 Cl -0.3735(7) -0.0125(3) 0.4954(3) 0.0717(16) Uani 0.50 d PD . . O21 O -0.277(2) 0.0190(8) 0.4395(12) 0.120(8) Uani 0.50 d PD . . O22 O -0.4404(19) -0.0696(8) 0.4610(12) 0.109(7) Uani 0.50 d PD . . O23 O -0.474(2) 0.0343(9) 0.5212(14) 0.125(9) Uani 0.50 d PD . . O24 O -0.274(2) -0.0324(10) 0.5637(12) 0.183(14) Uani 0.50 d PD . . Cl3 Cl 0.0000 0.0000 1.0000 0.0510(8) Uani 1 d S . . O300 O -0.4250(11) 0.4681(5) 0.7539(7) 0.112(3) Uani 1 d . . . O400 O 0.4472(17) 0.0480(8) 0.7239(10) 0.077(4) Uiso 0.50 d P . . O500 O -0.627(3) 0.5277(13) 0.8587(17) 0.051(6) Uiso 0.25 d P A 1 O600 O -0.641(2) 0.5320(10) 0.8050(13) 0.025(4) Uiso 0.25 d P B 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 Cu2 0.0133(3) 0.0148(4) 0.0231(4) -0.0009(3) 0.0045(3) -0.0010(3) Cl1 0.0155(7) 0.0296(10) 0.0358(9) 0.0001(7) 0.0070(6) -0.0033(6) O1 0.018(2) 0.011(2) 0.029(3) -0.003(2) 0.0006(18) 0.0022(17) O2 0.026(2) 0.015(3) 0.026(3) 0.000(2) -0.004(2) 0.0020(19) O3 0.038(3) 0.024(3) 0.052(4) -0.015(3) 0.024(3) -0.008(2) Cu1 0.0136(3) 0.0166(4) 0.0135(4) 0.0046(3) 0.0018(3) -0.0005(3) N1 0.014(2) 0.022(3) 0.020(3) 0.007(2) -0.001(2) 0.002(2) C2 0.019(3) 0.033(4) 0.017(3) 0.007(3) 0.003(3) 0.002(3) C3 0.029(3) 0.027(4) 0.018(3) 0.000(3) 0.000(3) 0.002(3) N4 0.022(3) 0.016(3) 0.019(3) 0.003(2) 0.000(2) 0.000(2) C5 0.025(3) 0.027(4) 0.026(4) 0.002(3) -0.004(3) -0.002(3) C6 0.023(3) 0.026(4) 0.032(4) 0.002(3) -0.007(3) -0.010(3) C7 0.013(3) 0.032(4) 0.025(3) 0.016(3) 0.001(3) -0.001(3) N8 0.018(2) 0.013(3) 0.020(3) 0.008(2) 0.005(2) 0.002(2) C9 0.023(3) 0.024(4) 0.036(4) 0.004(3) 0.012(3) 0.003(3) C10 0.041(4) 0.026(4) 0.020(3) 0.000(3) 0.010(3) 0.002(3) N11 0.026(3) 0.020(3) 0.021(3) 0.006(2) 0.002(2) 0.003(2) C12 0.035(4) 0.029(4) 0.023(4) -0.001(3) -0.009(3) 0.001(3) C13 0.026(3) 0.033(4) 0.033(4) 0.001(3) -0.008(3) -0.003(3) C14 0.013(3) 0.036(5) 0.033(4) 0.006(3) -0.005(3) 0.000(3) C15 0.017(3) 0.024(4) 0.028(4) 0.012(3) 0.002(3) -0.001(3) C16 0.016(3) 0.013(3) 0.014(3) -0.003(3) 0.002(2) -0.001(2) C19 0.024(3) 0.022(4) 0.027(4) 0.011(3) 0.004(3) 0.007(3) C18 0.033(4) 0.029(5) 0.036(4) 0.012(4) 0.000(3) 0.011(3) C17 0.029(4) 0.024(4) 0.029(4) 0.002(3) 0.002(3) 0.006(3) O181 0.021(2) 0.025(3) 0.021(2) 0.006(2) -0.0025(18) 0.0018(19) O182 0.137(7) 0.042(4) 0.059(4) -0.009(3) -0.048(4) 0.045(4) C20 0.023(3) 0.030(5) 0.023(4) 0.006(3) -0.001(3) 0.008(3) O201 0.031(3) 0.034(3) 0.062(4) 0.012(3) 0.028(3) 0.001(2) O202 0.035(3) 0.028(3) 0.039(3) 0.010(2) 0.012(2) -0.009(2) O161 0.017(2) 0.019(2) 0.016(2) 0.0069(19) 0.0033(17) 0.0007(17) O162 0.015(2) 0.022(3) 0.024(2) 0.015(2) 0.0021(18) -0.0016(18) Cl2 0.110(5) 0.049(3) 0.055(3) 0.007(3) 0.001(3) -0.019(3) O21 0.143(17) 0.080(13) 0.144(18) 0.042(12) 0.083(15) 0.014(12) O22 0.111(16) 0.072(13) 0.137(19) -0.028(12) -0.049(14) -0.015(11) O23 0.093(15) 0.14(2) 0.15(2) -0.056(17) 0.048(15) 0.001(15) O24 0.26(3) 0.14(2) 0.13(2) 0.030(16) -0.15(2) -0.07(2) Cl3 0.0498(17) 0.050(2) 0.0539(19) 0.0011(15) 0.0064(15) -0.0007(14) O300 0.119(8) 0.097(7) 0.121(8) -0.012(6) 0.020(6) -0.034(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 Cu2 O1 1.944(4) . ? Cu2 O3 1.952(5) . ? Cu2 O161 2.015(4) . ? Cu2 Cl1 2.2558(16) . ? Cu2 O2 2.311(5) . ? O1 HA 0.827(10) . ? O1 HB 0.830(10) . ? O2 HC 0.828(10) . ? O2 HD 0.827(10) . ? O3 HE 0.81(2) . ? O3 HF 0.82(2) . ? Cu1 N11 2.011(6) . ? Cu1 N4 2.076(5) . ? Cu1 N8 2.080(5) . ? Cu1 N1 2.099(5) . ? Cu1 O162 2.257(4) . ? Cu1 O181 2.290(4) . ? N1 C15 1.488(8) . ? N1 C2 1.490(9) . ? N1 C14 1.498(8) . ? C2 C3 1.510(9) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N4 1.488(8) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N4 C5 1.485(8) . ? N4 C17 1.490(9) . ? C5 C6 1.530(9) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.518(10) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N8 1.504(8) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? N8 C19 1.473(8) . ? N8 C9 1.489(9) . ? C9 C10 1.513(10) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N11 1.484(8) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? N11 C12 1.477(8) . ? N11 H11 0.9300 . ? C12 C13 1.524(10) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.512(10) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.518(8) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 O162 1.239(7) . ? C16 O161 1.271(7) . ? C19 C20 1.550(9) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C18 O182 1.248(9) . ? C18 O181 1.248(9) . ? C18 C17 1.521(10) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C20 O202 1.222(9) . ? C20 O201 1.248(8) . ? Cl2 O22 1.362(14) . ? Cl2 O23 1.364(14) . ? Cl2 O21 1.407(13) . ? Cl2 O24 1.415(14) . ? Cl2 O23 1.44(2) 3_456 ? Cl2 Cl2 2.334(13) 3_456 ? O22 O23 1.08(2) 3_456 ? O23 O22 1.08(2) 3_456 ? O23 Cl2 1.44(2) 3_456 ? O23 O23 1.56(4) 3_456 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu2 O3 173.5(2) . . ? O1 Cu2 O161 86.73(18) . . ? O3 Cu2 O161 89.0(2) . . ? O1 Cu2 Cl1 92.10(14) . . ? O3 Cu2 Cl1 93.58(16) . . ? O161 Cu2 Cl1 159.61(13) . . ? O1 Cu2 O2 87.95(18) . . ? O3 Cu2 O2 86.9(2) . . ? O161 Cu2 O2 87.11(16) . . ? Cl1 Cu2 O2 113.21(12) . . ? Cu2 O1 HA 124(4) . . ? Cu2 O1 HB 121(4) . . ? HA O1 HB 106.6(18) . . ? Cu2 O2 HC 110(5) . . ? Cu2 O2 HD 105(5) . . ? HC O2 HD 107.0(18) . . ? Cu2 O3 HE 116(6) . . ? Cu2 O3 HF 116(5) . . ? HE O3 HF 110(4) . . ? N11 Cu1 N4 178.0(2) . . ? N11 Cu1 N8 86.6(2) . . ? N4 Cu1 N8 95.3(2) . . ? N11 Cu1 N1 91.2(2) . . ? N4 Cu1 N1 87.0(2) . . ? N8 Cu1 N1 172.2(2) . . ? N11 Cu1 O162 91.6(2) . . ? N4 Cu1 O162 88.70(18) . . ? N8 Cu1 O162 92.59(17) . . ? N1 Cu1 O162 80.03(17) . . ? N11 Cu1 O181 99.7(2) . . ? N4 Cu1 O181 79.66(18) . . ? N8 Cu1 O181 97.92(18) . . ? N1 Cu1 O181 89.78(18) . . ? O162 Cu1 O181 164.94(16) . . ? C15 N1 C2 110.2(5) . . ? C15 N1 C14 110.4(5) . . ? C2 N1 C14 108.8(5) . . ? C15 N1 Cu1 110.5(3) . . ? C2 N1 Cu1 103.1(4) . . ? C14 N1 Cu1 113.5(4) . . ? N1 C2 C3 109.5(5) . . ? N1 C2 H2A 109.8 . . ? C3 C2 H2A 109.8 . . ? N1 C2 H2B 109.8 . . ? C3 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? N4 C3 C2 110.3(5) . . ? N4 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? N4 C3 H3B 109.6 . . ? C2 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? C5 N4 C3 108.1(5) . . ? C5 N4 C17 110.4(5) . . ? C3 N4 C17 109.1(5) . . ? C5 N4 Cu1 113.9(4) . . ? C3 N4 Cu1 104.3(4) . . ? C17 N4 Cu1 110.8(4) . . ? N4 C5 C6 115.0(5) . . ? N4 C5 H5A 108.5 . . ? C6 C5 H5A 108.5 . . ? N4 C5 H5B 108.5 . . ? C6 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? C7 C6 C5 114.9(6) . . ? C7 C6 H6A 108.5 . . ? C5 C6 H6A 108.5 . . ? C7 C6 H6B 108.5 . . ? C5 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? N8 C7 C6 114.2(5) . . ? N8 C7 H7A 108.7 . . ? C6 C7 H7A 108.7 . . ? N8 C7 H7B 108.7 . . ? C6 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C19 N8 C9 111.7(5) . . ? C19 N8 C7 110.6(5) . . ? C9 N8 C7 109.5(5) . . ? C19 N8 Cu1 111.6(4) . . ? C9 N8 Cu1 102.4(4) . . ? C7 N8 Cu1 110.8(4) . . ? N8 C9 C10 109.6(5) . . ? N8 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? N8 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? N11 C10 C9 107.3(5) . . ? N11 C10 H10A 110.3 . . ? C9 C10 H10A 110.3 . . ? N11 C10 H10B 110.3 . . ? C9 C10 H10B 110.3 . . ? H10A C10 H10B 108.5 . . ? C12 N11 C10 111.9(5) . . ? C12 N11 Cu1 117.1(4) . . ? C10 N11 Cu1 107.7(4) . . ? C12 N11 H11 106.5 . . ? C10 N11 H11 106.5 . . ? Cu1 N11 H11 106.5 . . ? N11 C12 C13 111.2(5) . . ? N11 C12 H12A 109.4 . . ? C13 C12 H12A 109.4 . . ? N11 C12 H12B 109.4 . . ? C13 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C14 C13 C12 115.9(6) . . ? C14 C13 H13A 108.3 . . ? C12 C13 H13A 108.3 . . ? C14 C13 H13B 108.3 . . ? C12 C13 H13B 108.3 . . ? H13A C13 H13B 107.4 . . ? N1 C14 C13 115.0(5) . . ? N1 C14 H14A 108.5 . . ? C13 C14 H14A 108.5 . . ? N1 C14 H14B 108.5 . . ? C13 C14 H14B 108.5 . . ? H14A C14 H14B 107.5 . . ? N1 C15 C16 113.4(5) . . ? N1 C15 H15A 108.9 . . ? C16 C15 H15A 108.9 . . ? N1 C15 H15B 108.9 . . ? C16 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? O162 C16 O161 123.2(5) . . ? O162 C16 C15 121.3(5) . . ? O161 C16 C15 115.4(5) . . ? N8 C19 C20 119.3(5) . . ? N8 C19 H19A 107.5 . . ? C20 C19 H19A 107.5 . . ? N8 C19 H19B 107.5 . . ? C20 C19 H19B 107.5 . . ? H19A C19 H19B 107.0 . . ? O182 C18 O181 125.7(7) . . ? O182 C18 C17 114.4(7) . . ? O181 C18 C17 119.8(6) . . ? N4 C17 C18 115.4(6) . . ? N4 C17 H17A 108.4 . . ? C18 C17 H17A 108.4 . . ? N4 C17 H17B 108.4 . . ? C18 C17 H17B 108.4 . . ? H17A C17 H17B 107.5 . . ? C18 O181 Cu1 111.4(4) . . ? O202 C20 O201 126.8(7) . . ? O202 C20 C19 115.7(6) . . ? O201 C20 C19 117.4(6) . . ? C16 O161 Cu2 106.1(3) . . ? C16 O162 Cu1 111.2(4) . . ? O22 Cl2 O23 112.4(12) . . ? O22 Cl2 O21 112.3(11) . . ? O23 Cl2 O21 109.3(10) . . ? O22 Cl2 O24 109.0(10) . . ? O23 Cl2 O24 110.9(12) . . ? O21 Cl2 O24 102.4(11) . . ? O22 Cl2 O23 45.1(10) . 3_456 ? O23 Cl2 O23 67.3(13) . 3_456 ? O21 Cl2 O23 128.5(14) . 3_456 ? O24 Cl2 O23 127.5(15) . 3_456 ? O22 Cl2 Cl2 77.7(8) . 3_456 ? O23 Cl2 Cl2 34.7(9) . 3_456 ? O21 Cl2 Cl2 125.3(9) . 3_456 ? O24 Cl2 Cl2 125.8(11) . 3_456 ? O23 Cl2 Cl2 32.6(6) 3_456 3_456 ? O23 O22 Cl2 71.3(16) 3_456 . ? O22 O23 Cl2 176(2) 3_456 . ? O22 O23 Cl2 63.6(14) 3_456 3_456 ? Cl2 O23 Cl2 112.7(13) . 3_456 ? O22 O23 O23 118(2) 3_456 3_456 ? Cl2 O23 O23 58.7(10) . 3_456 ? Cl2 O23 O23 54.0(12) 3_456 3_456 ? _diffrn_measured_fraction_theta_max 0.899 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.899 _refine_diff_density_max 1.289 _refine_diff_density_min -1.305 _refine_diff_density_rms 0.146 #==END