# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2010 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Starosta, Radosaw' _publ_contact_author_email sta@wchuwr.pl _publ_section_title ; Copper(I) iodide complexes containing new aliphatic aminophosphine ligands and diimines - luminescent properties and antibacterial activity ; loop_ _publ_author_name R.Starosta M.Florek J.Kurl M.Puchalska A.Kochel data_rad3y _database_code_depnum_ccdc_archive 'CCDC 747837' #TrackingRef 'rad3y.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'tris((4-methylpiperazin-1-yl)methyl)phosphine' ; _chemical_name_common tris((4-methylpiperazin-1-yl)methyl)phosphine _chemical_melting_point ? _chemical_formula_moiety 'C18 H39 N6 P' _chemical_formula_sum 'C18 H39 N6 P' _chemical_formula_weight 370.52 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' P P 0.1023 0.0942 '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 _symmetry_space_group_name_Hall '-P 2ybc' 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 7.214(2) _cell_length_b 24.228(3) _cell_length_c 12.995(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.46(2) _cell_angle_gamma 90.00 _cell_volume 2166.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4151 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 36.97 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.136 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.867 _exptl_absorpt_correction_T_max 0.910 _exptl_absorpt_process_details 'Oxford Diffraction, CrysAlis 1.171.30' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KM4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 39696 _diffrn_reflns_av_R_equivalents 0.0828 _diffrn_reflns_av_sigmaI/netI 0.1330 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 36.97 _reflns_number_total 9523 _reflns_number_gt 4544 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, date)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, date)' _computing_data_reduction 'CrysAlis RED ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXL-97 _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^)+(0.0530P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9523 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1409 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1249 _refine_ls_wR_factor_gt 0.0979 _refine_ls_goodness_of_fit_ref 0.946 _refine_ls_restrained_S_all 0.946 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.30969(5) 0.121306(15) 0.45335(3) 0.01939(9) Uani 1 1 d . . . N11 N 0.36896(15) 0.11954(5) 0.25258(9) 0.0178(2) Uani 1 1 d . . . C11 C 0.22395(19) 0.10565(6) 0.30709(11) 0.0193(3) Uani 1 1 d . . . H11A H 0.1932 0.0667 0.2972 0.028(4) Uiso 1 1 d R . . H11B H 0.1058 0.1262 0.2740 0.024(4) Uiso 1 1 d R . . C12 C 0.27531(19) 0.12229(6) 0.13603(11) 0.0207(3) Uani 1 1 d . . . H12A H 0.2157 0.0870 0.1105 0.021(4) Uiso 1 1 d R . . H12B H 0.1738 0.1501 0.1203 0.015(4) Uiso 1 1 d R . . C13 C 0.4219(2) 0.13652(6) 0.07779(11) 0.0226(3) Uani 1 1 d . . . H13A H 0.4776 0.1725 0.1012 0.029(4) Uiso 1 1 d R . . H13B H 0.3573 0.1382 0.0008 0.022(4) Uiso 1 1 d R . . N14 N 0.57577(17) 0.09528(5) 0.09998(9) 0.0221(3) Uani 1 1 d . . . C15 C 0.67068(19) 0.09246(6) 0.21652(11) 0.0208(3) Uani 1 1 d . . . H15A H 0.7305 0.1277 0.2421 0.016(4) Uiso 1 1 d R . . H15B H 0.7720 0.0646 0.2319 0.018(4) Uiso 1 1 d R . . C16 C 0.52382(19) 0.07824(6) 0.27475(11) 0.0187(3) Uani 1 1 d . . . H16A H 0.4682 0.0422 0.2514 0.020(4) Uiso 1 1 d R . . H16B H 0.5884 0.0766 0.3518 0.018(4) Uiso 1 1 d R . . C17 C 0.7172(2) 0.10881(7) 0.04376(13) 0.0315(4) Uani 1 1 d . . . H17A H 0.8179 0.0814 0.0597 0.039(5) Uiso 1 1 d R . . H17B H 0.6537 0.1096 -0.0326 0.038(5) Uiso 1 1 d R . . H17C H 0.7731 0.1443 0.0671 0.046(6) Uiso 1 1 d R . . N21 N 0.06815(16) 0.21428(5) 0.38797(9) 0.0204(2) Uani 1 1 d . . . C21 C 0.2680(2) 0.19717(6) 0.44374(13) 0.0257(3) Uani 1 1 d . . . H21A H 0.3532 0.2132 0.4066 0.038(5) Uiso 1 1 d R . . H21B H 0.3050 0.2123 0.5162 0.041(5) Uiso 1 1 d R . . C22 C -0.0318(2) 0.23469(6) 0.46311(12) 0.0237(3) Uani 1 1 d . . . H22A H 0.0320 0.2679 0.4983 0.027(4) Uiso 1 1 d R . . H22B H -0.0254 0.2071 0.5182 0.028(4) Uiso 1 1 d R . . C23 C -0.2418(2) 0.24726(6) 0.40337(13) 0.0245(3) Uani 1 1 d . . . H23A H -0.3072 0.2137 0.3713 0.025(4) Uiso 1 1 d R . . H23B H -0.3065 0.2612 0.4536 0.026(4) Uiso 1 1 d R . . N24 N -0.25422(17) 0.28814(5) 0.31906(10) 0.0249(3) Uani 1 1 d . . . C25 C -0.1552(2) 0.26723(6) 0.24396(13) 0.0263(3) Uani 1 1 d . . . H25A H -0.2185 0.2338 0.2099 0.021(4) Uiso 1 1 d R . . H25B H -0.1629 0.2944 0.1880 0.023(4) Uiso 1 1 d R . . C26 C 0.0557(2) 0.25525(6) 0.30364(12) 0.0232(3) Uani 1 1 d . . . H26A H 0.1202 0.2890 0.3357 0.027(4) Uiso 1 1 d R . . H26B H 0.1208 0.2415 0.2535 0.032(5) Uiso 1 1 d R . . C27 C -0.4565(2) 0.30100(7) 0.26197(15) 0.0367(4) Uani 1 1 d . . . H27A H -0.5229 0.2679 0.2304 0.044(5) Uiso 1 1 d R . . H27B H -0.5181 0.3160 0.3118 0.039(5) Uiso 1 1 d R . . H27C H -0.4618 0.3275 0.2062 0.034(5) Uiso 1 1 d R . . N31 N 0.08151(15) 0.09788(4) 0.58987(9) 0.0170(2) Uani 1 1 d . . . C31 C 0.08443(19) 0.09582(6) 0.47766(11) 0.0187(3) Uani 1 1 d . . . H31B H -0.0240 0.1174 0.4339 0.018(4) Uiso 1 1 d R . . H31A H 0.0638 0.0579 0.4530 0.024(4) Uiso 1 1 d R . . C32 C 0.23052(19) 0.06170(6) 0.65876(11) 0.0202(3) Uani 1 1 d . . . H32A H 0.2134 0.0245 0.6297 0.022(4) Uiso 1 1 d R . . H32B H 0.3582 0.0745 0.6593 0.024(4) Uiso 1 1 d R . . C33 C 0.2178(2) 0.06103(6) 0.77257(11) 0.0224(3) Uani 1 1 d . . . H33A H 0.2374 0.0981 0.8022 0.028(4) Uiso 1 1 d R . . H33B H 0.3194 0.0376 0.8172 0.025(4) Uiso 1 1 d R . . N34 N 0.02853(17) 0.04051(5) 0.77398(10) 0.0219(2) Uani 1 1 d . . . C35 C -0.1222(2) 0.07649(6) 0.70715(12) 0.0238(3) Uani 1 1 d . . . H35A H -0.1078 0.1132 0.7384 0.029(4) Uiso 1 1 d R . . H35B H -0.2489 0.0625 0.7059 0.026(4) Uiso 1 1 d R . . C36 C -0.11070(19) 0.07977(6) 0.59321(11) 0.0199(3) Uani 1 1 d . . . H36A H -0.1391 0.0438 0.5595 0.030(4) Uiso 1 1 d R . . H36B H -0.2083 0.1054 0.5522 0.029(4) Uiso 1 1 d R . . C37 C 0.0157(3) 0.03948(7) 0.88365(12) 0.0328(4) Uani 1 1 d . . . H37A H 0.1223 0.0186 0.9289 0.041(5) Uiso 1 1 d R . . H37B H -0.1047 0.0226 0.8839 0.044(5) Uiso 1 1 d R . . H37C H 0.0209 0.0765 0.9106 0.034(5) Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.01734(16) 0.02391(17) 0.01735(18) 0.00013(14) 0.00584(12) 0.00066(14) N11 0.0159(5) 0.0221(5) 0.0165(6) 0.0014(4) 0.0063(4) 0.0022(4) C11 0.0183(6) 0.0248(7) 0.0146(6) -0.0001(5) 0.0048(5) 0.0005(5) C12 0.0175(6) 0.0263(7) 0.0182(7) 0.0010(6) 0.0052(5) 0.0019(5) C13 0.0233(7) 0.0278(7) 0.0168(7) 0.0033(5) 0.0060(5) 0.0025(5) N14 0.0222(6) 0.0273(6) 0.0186(6) -0.0008(5) 0.0087(5) 0.0019(5) C15 0.0182(6) 0.0218(7) 0.0228(7) -0.0015(5) 0.0068(5) 0.0012(5) C16 0.0187(6) 0.0231(7) 0.0136(6) 0.0003(5) 0.0036(5) 0.0018(5) C17 0.0294(8) 0.0418(10) 0.0292(9) 0.0023(7) 0.0176(7) 0.0043(7) N21 0.0215(6) 0.0197(5) 0.0214(6) 0.0021(5) 0.0087(5) 0.0012(4) C21 0.0190(7) 0.0239(7) 0.0329(9) -0.0030(6) 0.0061(6) -0.0040(5) C22 0.0281(7) 0.0229(7) 0.0237(8) -0.0024(6) 0.0131(6) -0.0014(6) C23 0.0256(7) 0.0221(7) 0.0300(8) -0.0031(6) 0.0146(6) 0.0006(6) N24 0.0229(6) 0.0214(6) 0.0300(7) 0.0000(5) 0.0073(5) 0.0023(5) C25 0.0334(8) 0.0197(7) 0.0276(8) -0.0001(6) 0.0120(6) -0.0017(6) C26 0.0278(7) 0.0209(7) 0.0248(8) 0.0002(6) 0.0137(6) -0.0028(6) C27 0.0304(9) 0.0306(9) 0.0464(11) -0.0010(8) 0.0077(8) 0.0054(7) N31 0.0168(5) 0.0193(5) 0.0152(6) 0.0027(4) 0.0052(4) 0.0016(4) C31 0.0197(6) 0.0209(6) 0.0153(7) -0.0026(5) 0.0048(5) -0.0021(5) C32 0.0192(6) 0.0231(7) 0.0175(7) 0.0041(5) 0.0042(5) 0.0036(5) C33 0.0266(7) 0.0238(7) 0.0162(7) 0.0011(5) 0.0056(5) -0.0020(5) N34 0.0301(6) 0.0190(6) 0.0192(6) 0.0004(5) 0.0112(5) -0.0025(5) C35 0.0262(7) 0.0226(7) 0.0269(8) 0.0015(6) 0.0145(6) 0.0009(6) C36 0.0187(6) 0.0229(7) 0.0186(7) 0.0021(5) 0.0065(5) 0.0009(5) C37 0.0487(10) 0.0343(9) 0.0195(8) 0.0018(7) 0.0163(7) -0.0036(8) _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 P1 C31 1.8520(14) . ? P1 C11 1.8530(14) . ? P1 C21 1.8606(15) . ? N11 C16 1.4627(17) . ? N11 C12 1.4632(17) . ? N11 C11 1.4677(17) . ? C11 H11A 0.9701 . ? C11 H11B 0.9700 . ? C12 C13 1.5130(19) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N14 1.4567(18) . ? C13 H13A 0.9701 . ? C13 H13B 0.9700 . ? N14 C17 1.4594(18) . ? N14 C15 1.4645(18) . ? C15 C16 1.5149(19) . ? C15 H15A 0.9701 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9701 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9599 . ? N21 C26 1.4612(18) . ? N21 C22 1.4630(18) . ? N21 C21 1.4656(18) . ? C21 H21A 0.9700 . ? C21 H21B 0.9699 . ? C22 C23 1.511(2) . ? C22 H22A 0.9699 . ? C22 H22B 0.9701 . ? C23 N24 1.4597(19) . ? C23 H23A 0.9699 . ? C23 H23B 0.9698 . ? N24 C27 1.458(2) . ? N24 C25 1.462(2) . ? C25 C26 1.514(2) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9700 . ? C26 H26B 0.9699 . ? C27 H27A 0.9601 . ? C27 H27B 0.9599 . ? C27 H27C 0.9600 . ? N31 C31 1.4654(17) . ? N31 C32 1.4656(17) . ? N31 C36 1.4674(17) . ? C31 H31B 0.9699 . ? C31 H31A 0.9703 . ? C32 C33 1.5090(19) . ? C32 H32A 0.9700 . ? C32 H32B 0.9701 . ? C33 N34 1.4586(18) . ? C33 H33A 0.9699 . ? C33 H33B 0.9701 . ? N34 C37 1.4559(19) . ? N34 C35 1.4594(19) . ? C35 C36 1.5097(19) . ? C35 H35A 0.9700 . ? C35 H35B 0.9699 . ? C36 H36A 0.9702 . ? C36 H36B 0.9699 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9599 . ? 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 C31 P1 C11 93.83(6) . . ? C31 P1 C21 102.02(6) . . ? C11 P1 C21 97.81(7) . . ? C16 N11 C12 108.86(10) . . ? C16 N11 C11 111.15(11) . . ? C12 N11 C11 109.60(10) . . ? N11 C11 P1 112.41(9) . . ? N11 C11 H11A 109.1 . . ? P1 C11 H11A 109.1 . . ? N11 C11 H11B 109.1 . . ? P1 C11 H11B 109.1 . . ? H11A C11 H11B 107.9 . . ? N11 C12 C13 110.68(11) . . ? N11 C12 H12A 109.5 . . ? C13 C12 H12A 109.5 . . ? N11 C12 H12B 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? N14 C13 C12 110.51(11) . . ? N14 C13 H13A 109.5 . . ? C12 C13 H13A 109.5 . . ? N14 C13 H13B 109.6 . . ? C12 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? C13 N14 C17 110.66(11) . . ? C13 N14 C15 109.20(11) . . ? C17 N14 C15 110.37(11) . . ? N14 C15 C16 110.32(11) . . ? N14 C15 H15A 109.6 . . ? C16 C15 H15A 109.6 . . ? N14 C15 H15B 109.6 . . ? C16 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? N11 C16 C15 110.69(11) . . ? N11 C16 H16A 109.5 . . ? C15 C16 H16A 109.5 . . ? N11 C16 H16B 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? N14 C17 H17A 109.5 . . ? N14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C26 N21 C22 109.84(11) . . ? C26 N21 C21 113.14(11) . . ? C22 N21 C21 111.97(12) . . ? N21 C21 P1 115.34(9) . . ? N21 C21 H21A 108.4 . . ? P1 C21 H21A 108.4 . . ? N21 C21 H21B 108.5 . . ? P1 C21 H21B 108.4 . . ? H21A C21 H21B 107.5 . . ? N21 C22 C23 110.12(12) . . ? N21 C22 H22A 109.6 . . ? C23 C22 H22A 109.6 . . ? N21 C22 H22B 109.6 . . ? C23 C22 H22B 109.6 . . ? H22A C22 H22B 108.1 . . ? N24 C23 C22 110.40(12) . . ? N24 C23 H23A 109.6 . . ? C22 C23 H23A 109.6 . . ? N24 C23 H23B 109.6 . . ? C22 C23 H23B 109.6 . . ? H23A C23 H23B 108.1 . . ? C27 N24 C23 110.70(12) . . ? C27 N24 C25 110.43(13) . . ? C23 N24 C25 109.49(11) . . ? N24 C25 C26 109.98(12) . . ? N24 C25 H25A 109.7 . . ? C26 C25 H25A 109.7 . . ? N24 C25 H25B 109.7 . . ? C26 C25 H25B 109.7 . . ? H25A C25 H25B 108.2 . . ? N21 C26 C25 109.91(11) . . ? N21 C26 H26A 109.7 . . ? C25 C26 H26A 109.7 . . ? N21 C26 H26B 109.7 . . ? C25 C26 H26B 109.7 . . ? H26A C26 H26B 108.2 . . ? N24 C27 H27A 109.5 . . ? N24 C27 H27B 109.4 . . ? H27A C27 H27B 109.5 . . ? N24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C31 N31 C32 111.13(10) . . ? C31 N31 C36 108.36(10) . . ? C32 N31 C36 109.23(11) . . ? N31 C31 P1 115.70(9) . . ? N31 C31 H31B 108.4 . . ? P1 C31 H31B 108.4 . . ? N31 C31 H31A 108.4 . . ? P1 C31 H31A 108.3 . . ? H31B C31 H31A 107.4 . . ? N31 C32 C33 110.86(11) . . ? N31 C32 H32A 109.5 . . ? C33 C32 H32A 109.5 . . ? N31 C32 H32B 109.5 . . ? C33 C32 H32B 109.5 . . ? H32A C32 H32B 108.1 . . ? N34 C33 C32 110.39(11) . . ? N34 C33 H33A 109.6 . . ? C32 C33 H33A 109.6 . . ? N34 C33 H33B 109.6 . . ? C32 C33 H33B 109.6 . . ? H33A C33 H33B 108.1 . . ? C37 N34 C33 110.68(12) . . ? C37 N34 C35 109.74(12) . . ? C33 N34 C35 108.80(11) . . ? N34 C35 C36 111.38(11) . . ? N34 C35 H35A 109.4 . . ? C36 C35 H35A 109.4 . . ? N34 C35 H35B 109.3 . . ? C36 C35 H35B 109.3 . . ? H35A C35 H35B 108.0 . . ? N31 C36 C35 112.04(11) . . ? N31 C36 H36A 109.2 . . ? C35 C36 H36A 109.2 . . ? N31 C36 H36B 109.2 . . ? C35 C36 H36B 109.2 . . ? H36A C36 H36B 107.9 . . ? N34 C37 H37A 109.5 . . ? N34 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? N34 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C11 P1 76.61(12) . . . . ? C12 N11 C11 P1 -163.02(9) . . . . ? C31 P1 C11 N11 -179.04(10) . . . . ? C21 P1 C11 N11 78.25(10) . . . . ? C16 N11 C12 C13 -58.18(14) . . . . ? C11 N11 C12 C13 -179.94(11) . . . . ? N11 C12 C13 N14 59.28(15) . . . . ? C12 C13 N14 C17 179.89(12) . . . . ? C12 C13 N14 C15 -58.43(15) . . . . ? C13 N14 C15 C16 58.32(14) . . . . ? C17 N14 C15 C16 -179.83(12) . . . . ? C12 N11 C16 C15 58.18(14) . . . . ? C11 N11 C16 C15 179.00(11) . . . . ? N14 C15 C16 N11 -59.08(14) . . . . ? C26 N21 C21 P1 -129.22(11) . . . . ? C22 N21 C21 P1 106.01(12) . . . . ? C31 P1 C21 N21 -38.31(12) . . . . ? C11 P1 C21 N21 57.32(12) . . . . ? C26 N21 C22 C23 58.21(15) . . . . ? C21 N21 C22 C23 -175.20(11) . . . . ? N21 C22 C23 N24 -58.49(15) . . . . ? C22 C23 N24 C27 -179.27(12) . . . . ? C22 C23 N24 C25 58.76(15) . . . . ? C27 N24 C25 C26 178.73(12) . . . . ? C23 N24 C25 C26 -59.13(15) . . . . ? C22 N21 C26 C25 -58.71(15) . . . . ? C21 N21 C26 C25 175.36(11) . . . . ? N24 C25 C26 N21 59.44(15) . . . . ? C32 N31 C31 P1 -63.66(13) . . . . ? C36 N31 C31 P1 176.32(9) . . . . ? C11 P1 C31 N31 178.18(10) . . . . ? C21 P1 C31 N31 -82.99(11) . . . . ? C31 N31 C32 C33 -176.14(11) . . . . ? C36 N31 C32 C33 -56.64(14) . . . . ? N31 C32 C33 N34 60.57(15) . . . . ? C32 C33 N34 C37 179.70(12) . . . . ? C32 C33 N34 C35 -59.64(14) . . . . ? C37 N34 C35 C36 178.62(12) . . . . ? C33 N34 C35 C36 57.39(15) . . . . ? C31 N31 C36 C35 175.71(11) . . . . ? C32 N31 C36 C35 54.52(14) . . . . ? N34 C35 C36 N31 -56.01(15) . . . . ? _diffrn_measured_fraction_theta_max 0.866 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.507 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.059 #_publ_author_letter #; #Please consider this CIF as deposit in the Cambridge #Crystallographic Data Centre #; #================================================ # Attachment 's31.cif' data_s31 _database_code_depnum_ccdc_archive 'CCDC 747838' #TrackingRef 's31.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'bis(Iodo-(1,10-phenanthroline-N,N')- (tris(morpholinomethyl)phosphine-P)-copper(I)) bis((mu2-Iodo)- (1,10-phenanthroline-N,N')-copper(I))' ; _chemical_name_common ; 'bis(Iodo-(1,10-phenanthroline-N,N')-(tris(morpholinomethyl)phosphine-P)- copper(i)) bis((mu2-Iodo)-(1,10-phenanthroline-N,N')-copper(i))' ; _chemical_melting_point ? _chemical_formula_moiety 'C27 H38 Cu I N5 P, 0.5(C24 H16 Cu2 I2 N4)' _chemical_formula_sum 'C39 H46 Cu2 I2 N7 O3 P' _chemical_formula_weight 1072.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Cu Cu 0.3201 1.2651 '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' 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.675(3) _cell_length_b 10.196(5) _cell_length_c 23.342(4) _cell_angle_alpha 83.32(3) _cell_angle_beta 81.16(5) _cell_angle_gamma 63.86(4) _cell_volume 2039.5(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4611 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 25.06 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.747 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 2.642 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.683 _exptl_absorpt_correction_T_max 0.760 _exptl_absorpt_process_details 'Oxford Diffraction, CrysAlis 1.171.30' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KM4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11161 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0656 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 25.06 _reflns_number_total 6684 _reflns_number_gt 4633 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, date)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, date)' _computing_data_reduction 'CrysAlis RED ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXL-97 _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^)+(0.0409P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6684 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0619 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.0799 _refine_ls_wR_factor_gt 0.0713 _refine_ls_goodness_of_fit_ref 0.952 _refine_ls_restrained_S_all 0.952 _refine_ls_shift/su_max 0.148 _refine_ls_shift/su_mean 0.024 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 I1 I 0.71906(4) 0.16219(3) 0.029264(15) 0.02811(11) Uani 1 1 d . . . Cu1 Cu 0.78098(7) 0.27285(6) 0.11299(3) 0.02872(17) Uani 1 1 d . . . P1 P 0.67466(18) 0.21028(15) 0.19486(7) 0.0363(4) Uani 1 1 d . . . C11 C 0.6672(8) 0.2731(6) 0.2663(3) 0.0505(17) Uani 1 1 d . . . H11A H 0.5950 0.2461 0.2944 0.061 Uiso 1 1 calc R . . H11B H 0.7713 0.2218 0.2796 0.061 Uiso 1 1 calc R . . N11 N 0.6180(5) 0.4285(5) 0.26627(19) 0.0378(12) Uani 1 1 d . . . C12 C 0.5566(10) 0.4878(9) 0.3229(3) 0.084(3) Uani 1 1 d . . . H12A H 0.6377 0.4415 0.3495 0.101 Uiso 1 1 calc R . . H12B H 0.4683 0.4650 0.3389 0.101 Uiso 1 1 calc R . . C13 C 0.5035(10) 0.6508(10) 0.3192(5) 0.115(4) Uani 1 1 d . . . H13A H 0.4222 0.6969 0.2926 0.137 Uiso 1 1 calc R . . H13B H 0.4575 0.6892 0.3580 0.137 Uiso 1 1 calc R . . O14 O 0.6231(7) 0.6874(5) 0.2995(2) 0.0742(15) Uani 1 1 d . . . C15 C 0.6822(15) 0.6345(11) 0.2441(3) 0.120(4) Uani 1 1 d . . . H15A H 0.7669 0.6625 0.2280 0.144 Uiso 1 1 calc R . . H15B H 0.5995 0.6793 0.2181 0.144 Uiso 1 1 calc R . . C16 C 0.7422(10) 0.4727(9) 0.2462(3) 0.077(2) Uani 1 1 d . . . H16A H 0.7893 0.4371 0.2070 0.093 Uiso 1 1 calc R . . H16B H 0.8238 0.4279 0.2727 0.093 Uiso 1 1 calc R . . C21 C 0.4672(7) 0.2823(7) 0.1889(3) 0.0487(17) Uani 1 1 d . . . H21A H 0.4226 0.3905 0.1874 0.058 Uiso 1 1 calc R . . H21B H 0.4550 0.2540 0.1515 0.058 Uiso 1 1 calc R . . N21 N 0.3758(6) 0.2347(5) 0.2355(2) 0.0425(13) Uani 1 1 d . . . C22 C 0.3251(10) 0.1334(10) 0.2166(3) 0.081(3) Uani 1 1 d . . . H22A H 0.4166 0.0448 0.2027 0.098 Uiso 1 1 calc R . . H22B H 0.2624 0.1801 0.1839 0.098 Uiso 1 1 calc R . . C23 C 0.2307(10) 0.0911(9) 0.2654(3) 0.077(2) Uani 1 1 d . . . H23A H 0.1962 0.0233 0.2517 0.092 Uiso 1 1 calc R . . H23B H 0.2955 0.0394 0.2972 0.092 Uiso 1 1 calc R . . O24 O 0.1002(5) 0.2150(6) 0.28675(19) 0.0642(14) Uani 1 1 d . . . C25 C 0.1496(9) 0.3099(8) 0.3078(3) 0.066(2) Uani 1 1 d . . . H25A H 0.2150 0.2586 0.3394 0.080 Uiso 1 1 calc R . . H25B H 0.0584 0.3961 0.3237 0.080 Uiso 1 1 calc R . . C26 C 0.2414(8) 0.3593(7) 0.2588(3) 0.066(2) Uani 1 1 d . . . H26A H 0.1750 0.4127 0.2277 0.079 Uiso 1 1 calc R . . H26B H 0.2748 0.4269 0.2734 0.079 Uiso 1 1 calc R . . C31 C 0.7266(8) 0.0151(6) 0.2152(4) 0.071(2) Uani 1 1 d . . . H31A H 0.6637 0.0068 0.2519 0.085 Uiso 1 1 calc R . . H31B H 0.7019 -0.0283 0.1846 0.085 Uiso 1 1 calc R . . N31 N 0.8892(7) -0.0656(7) 0.2224(3) 0.091(3) Uani 1 1 d . . . C32 C 0.9872(8) -0.1065(7) 0.1718(3) 0.0525(18) Uani 1 1 d . . . H32A H 0.9777 -0.0162 0.1483 0.063 Uiso 1 1 calc R . . H32B H 0.9495 -0.1593 0.1498 0.063 Uiso 1 1 calc R . . C33 C 1.1520(8) -0.1979(7) 0.1763(3) 0.0553(18) Uani 1 1 d . . . H33A H 1.1941 -0.2603 0.1425 0.066 Uiso 1 1 calc R . . H33B H 1.2042 -0.1323 0.1722 0.066 Uiso 1 1 calc R . . O34 O 1.1939(6) -0.2855(7) 0.2241(3) 0.0904(19) Uani 1 1 d . . . C35 C 1.1039(13) -0.2420(8) 0.2730(4) 0.089(3) Uani 1 1 d . . . H35A H 1.1399 -0.1810 0.2910 0.106 Uiso 1 1 calc R . . H35B H 1.1220 -0.3301 0.2993 0.106 Uiso 1 1 calc R . . C36 C 0.9343(10) -0.1588(10) 0.2721(3) 0.075(2) Uani 1 1 d . . . H36A H 0.8881 -0.2292 0.2752 0.090 Uiso 1 1 calc R . . H36B H 0.8909 -0.0995 0.3067 0.090 Uiso 1 1 calc R . . N41 N 0.7155(5) 0.4983(4) 0.09700(19) 0.0304(11) Uani 1 1 d . . . N42 N 0.9956(5) 0.2703(4) 0.08803(18) 0.0263(10) Uani 1 1 d . . . C41 C 0.5756(7) 0.6094(6) 0.1011(3) 0.0383(15) Uani 1 1 d . . . H41 H 0.4875 0.5889 0.1083 0.046 Uiso 1 1 calc R . . C42 C 0.5524(7) 0.7561(5) 0.0952(3) 0.0369(15) Uani 1 1 d . . . H42 H 0.4504 0.8328 0.0989 0.044 Uiso 1 1 calc R . . C43 C 0.6765(7) 0.7876(6) 0.0844(2) 0.0357(14) Uani 1 1 d . . . H43 H 0.6622 0.8864 0.0809 0.043 Uiso 1 1 calc R . . C44 C 0.8281(6) 0.6714(5) 0.0783(2) 0.0255(12) Uani 1 1 d . . . C45 C 0.9639(7) 0.6950(6) 0.0625(2) 0.0300(13) Uani 1 1 d . . . H45 H 0.9555 0.7919 0.0565 0.036 Uiso 1 1 calc R . . C46 C 1.1033(7) 0.5809(6) 0.0560(2) 0.0306(13) Uani 1 1 d . . . H46 H 1.1923 0.5991 0.0456 0.037 Uiso 1 1 calc R . . C47 C 1.1235(6) 0.4323(6) 0.0642(2) 0.0266(13) Uani 1 1 d . . . C48 C 1.2648(6) 0.3115(6) 0.0548(2) 0.0317(13) Uani 1 1 d . . . H48 H 1.3571 0.3242 0.0443 0.038 Uiso 1 1 calc R . . C49 C 1.2712(7) 0.1750(6) 0.0606(2) 0.0363(14) Uani 1 1 d . . . H49 H 1.3674 0.0918 0.0538 0.044 Uiso 1 1 calc R . . C50 C 1.1333(6) 0.1586(6) 0.0769(2) 0.0320(13) Uani 1 1 d . . . H50 H 1.1390 0.0627 0.0802 0.038 Uiso 1 1 calc R . . C51 C 0.8382(6) 0.5306(5) 0.0864(2) 0.0245(12) Uani 1 1 d . . . C52 C 0.9902(6) 0.4067(5) 0.0799(2) 0.0264(12) Uani 1 1 d . . . Cu2 Cu 0.06687(7) 0.35873(6) 0.50236(3) 0.02891(17) Uani 1 1 d . . . I2 I -0.18267(4) 0.49325(4) 0.570339(16) 0.03259(11) Uani 1 1 d . . . N60 N 0.2353(5) 0.1850(4) 0.54512(18) 0.0246(10) Uani 1 1 d . . . N61 N 0.0701(5) 0.1862(4) 0.46177(17) 0.0245(10) Uani 1 1 d . . . C61 C -0.0140(6) 0.1871(6) 0.4221(2) 0.0285(13) Uani 1 1 d . . . H61 H -0.0902 0.2786 0.4091 0.034 Uiso 1 1 calc R . . C62 C 0.0033(6) 0.0604(6) 0.3981(2) 0.0320(13) Uani 1 1 d . . . H62 H -0.0591 0.0657 0.3694 0.038 Uiso 1 1 calc R . . C63 C 0.1127(6) -0.0720(6) 0.4172(2) 0.0302(13) Uani 1 1 d . . . H63 H 0.1262 -0.1595 0.4017 0.036 Uiso 1 1 calc R . . C64 C 0.2047(6) -0.0790(5) 0.4595(2) 0.0245(12) Uani 1 1 d . . . C65 C 0.3191(6) -0.2126(5) 0.4812(3) 0.0337(14) Uani 1 1 d . . . H65 H 0.3362 -0.3025 0.4668 0.040 Uiso 1 1 calc R . . C66 C 0.4036(6) -0.2128(6) 0.5221(3) 0.0335(14) Uani 1 1 d . . . H66 H 0.4808 -0.3030 0.5355 0.040 Uiso 1 1 calc R . . C67 C 0.3793(6) -0.0792(6) 0.5457(2) 0.0282(12) Uani 1 1 d . . . C68 C 0.4608(6) -0.0726(6) 0.5886(2) 0.0367(14) Uani 1 1 d . . . H68 H 0.5394 -0.1600 0.6033 0.044 Uiso 1 1 calc R . . C69 C 0.4295(6) 0.0578(6) 0.6097(2) 0.0329(13) Uani 1 1 d . . . H69 H 0.4834 0.0625 0.6396 0.040 Uiso 1 1 calc R . . C70 C 0.3163(6) 0.1834(6) 0.5863(2) 0.0330(13) Uani 1 1 d . . . H70 H 0.2956 0.2744 0.6007 0.040 Uiso 1 1 calc R . . C71 C 0.1800(6) 0.0538(5) 0.4806(2) 0.0248(12) Uani 1 1 d . . . C72 C 0.2678(6) 0.0532(5) 0.5242(2) 0.0248(12) 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 I1 0.0240(2) 0.02274(19) 0.0403(2) -0.00421(15) -0.00082(16) -0.01291(16) Cu1 0.0258(4) 0.0197(3) 0.0390(4) -0.0020(3) -0.0013(3) -0.0090(3) P1 0.0349(10) 0.0241(8) 0.0376(9) 0.0006(6) 0.0016(7) -0.0040(7) C11 0.061(5) 0.043(4) 0.037(4) 0.010(3) -0.012(3) -0.014(3) N11 0.038(3) 0.032(3) 0.031(3) -0.005(2) 0.002(2) -0.005(2) C12 0.087(7) 0.113(7) 0.072(6) -0.057(5) 0.054(5) -0.069(6) C13 0.048(6) 0.118(8) 0.175(10) -0.116(8) 0.016(6) -0.016(6) O14 0.105(5) 0.079(4) 0.050(3) -0.024(3) -0.013(3) -0.044(3) C15 0.257(14) 0.118(8) 0.044(5) -0.015(5) -0.004(7) -0.136(9) C16 0.097(7) 0.103(7) 0.044(4) -0.037(4) 0.042(4) -0.061(6) C21 0.041(4) 0.055(4) 0.038(4) 0.012(3) 0.007(3) -0.016(3) N21 0.040(3) 0.032(3) 0.042(3) -0.004(2) 0.009(2) -0.007(3) C22 0.086(6) 0.119(7) 0.058(5) -0.037(5) 0.033(4) -0.066(6) C23 0.083(7) 0.088(6) 0.074(6) -0.031(5) 0.020(5) -0.053(6) O24 0.046(3) 0.096(4) 0.038(3) 0.015(3) 0.002(2) -0.027(3) C25 0.073(6) 0.047(4) 0.061(5) -0.007(4) 0.031(4) -0.020(4) C26 0.070(5) 0.042(4) 0.058(5) 0.002(3) 0.027(4) -0.010(4) C31 0.041(5) 0.022(3) 0.117(7) 0.007(4) 0.024(4) 0.002(3) N31 0.067(5) 0.063(4) 0.061(4) 0.046(3) 0.029(4) 0.022(3) C32 0.064(5) 0.044(4) 0.037(4) -0.001(3) -0.014(4) -0.010(4) C33 0.050(5) 0.056(4) 0.040(4) -0.007(3) -0.012(3) -0.002(4) O34 0.061(4) 0.101(5) 0.095(5) 0.050(4) -0.033(4) -0.028(3) C35 0.150(10) 0.032(4) 0.055(6) 0.005(4) -0.050(6) -0.003(5) C36 0.110(7) 0.119(7) 0.026(4) -0.005(4) -0.009(4) -0.075(6) N41 0.026(3) 0.018(2) 0.045(3) -0.004(2) -0.004(2) -0.008(2) N42 0.021(3) 0.023(2) 0.032(3) 0.0004(19) -0.008(2) -0.006(2) C41 0.024(4) 0.020(3) 0.064(4) -0.005(3) -0.003(3) -0.003(3) C42 0.027(4) 0.012(3) 0.055(4) -0.004(2) -0.005(3) 0.008(2) C43 0.052(4) 0.026(3) 0.035(3) -0.004(2) -0.006(3) -0.021(3) C44 0.033(4) 0.027(3) 0.018(3) -0.003(2) -0.008(2) -0.013(3) C45 0.043(4) 0.027(3) 0.028(3) 0.000(2) -0.006(3) -0.022(3) C46 0.033(4) 0.044(3) 0.024(3) -0.001(3) -0.005(3) -0.024(3) C47 0.033(4) 0.029(3) 0.025(3) 0.006(2) -0.012(3) -0.018(3) C48 0.022(3) 0.036(3) 0.035(3) 0.010(3) -0.011(3) -0.011(3) C49 0.026(4) 0.041(4) 0.034(3) 0.000(3) -0.009(3) -0.007(3) C50 0.031(4) 0.024(3) 0.034(3) 0.001(2) -0.009(3) -0.005(3) C51 0.031(3) 0.018(3) 0.029(3) -0.001(2) -0.004(2) -0.015(3) C52 0.039(4) 0.028(3) 0.018(3) -0.001(2) -0.009(2) -0.018(3) Cu2 0.0289(4) 0.0203(3) 0.0329(4) 0.0015(3) -0.0015(3) -0.0077(3) I2 0.0295(2) 0.02319(19) 0.0365(2) 0.00231(15) 0.00634(17) -0.00775(17) N60 0.021(3) 0.019(2) 0.030(3) 0.0018(18) 0.001(2) -0.008(2) N61 0.024(3) 0.025(2) 0.021(2) -0.0003(18) 0.004(2) -0.009(2) C61 0.027(3) 0.030(3) 0.025(3) 0.006(2) 0.000(2) -0.011(3) C62 0.028(3) 0.040(3) 0.031(3) -0.002(3) 0.001(3) -0.019(3) C63 0.024(3) 0.027(3) 0.037(3) -0.009(2) 0.012(3) -0.011(3) C64 0.018(3) 0.029(3) 0.027(3) -0.002(2) 0.004(2) -0.013(2) C65 0.022(3) 0.015(3) 0.056(4) -0.003(3) 0.005(3) -0.004(2) C66 0.011(3) 0.020(3) 0.059(4) 0.006(3) 0.000(3) 0.000(2) C67 0.023(3) 0.030(3) 0.032(3) 0.008(2) -0.006(3) -0.014(3) C68 0.025(3) 0.026(3) 0.049(4) 0.011(3) 0.001(3) -0.007(3) C69 0.025(3) 0.035(3) 0.032(3) 0.006(3) -0.007(3) -0.008(3) C70 0.038(4) 0.036(3) 0.028(3) 0.000(3) -0.004(3) -0.019(3) C71 0.016(3) 0.023(3) 0.032(3) -0.001(2) 0.006(2) -0.008(2) C72 0.025(3) 0.017(3) 0.032(3) 0.003(2) 0.003(2) -0.012(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 Cu1 2.6307(10) . ? Cu1 N42 2.058(4) . ? Cu1 N41 2.101(4) . ? Cu1 P1 2.1926(19) . ? P1 C21 1.830(6) . ? P1 C11 1.835(6) . ? P1 C31 1.846(6) . ? C11 N11 1.439(7) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? N11 C12 1.447(8) . ? N11 C16 1.457(8) . ? C12 C13 1.503(11) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 O14 1.366(10) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? O14 C15 1.398(9) . ? C15 C16 1.486(11) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C21 N21 1.470(7) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? N21 C26 1.445(8) . ? N21 C22 1.456(8) . ? C22 C23 1.494(9) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 O24 1.409(9) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? O24 C25 1.413(8) . ? C25 C26 1.516(8) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C31 N31 1.445(9) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? N31 C32 1.376(8) . ? N31 C36 1.403(8) . ? C32 C33 1.463(8) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 O34 1.340(7) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? O34 C35 1.315(10) . ? C35 C36 1.481(11) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? N41 C41 1.326(6) . ? N41 C51 1.347(6) . ? N42 C50 1.328(6) . ? N42 C52 1.361(6) . ? C41 C42 1.405(7) . ? C41 H41 0.9500 . ? C42 C43 1.354(7) . ? C42 H42 0.9500 . ? C43 C44 1.421(8) . ? C43 H43 0.9500 . ? C44 C51 1.388(6) . ? C44 C45 1.424(7) . ? C45 C46 1.339(7) . ? C45 H45 0.9500 . ? C46 C47 1.432(7) . ? C46 H46 0.9500 . ? C47 C48 1.386(7) . ? C47 C52 1.413(7) . ? C48 C49 1.356(7) . ? C48 H48 0.9500 . ? C49 C50 1.406(7) . ? C49 H49 0.9500 . ? C50 H50 0.9500 . ? C51 C52 1.456(7) . ? Cu2 N61 2.079(4) . ? Cu2 N60 2.082(4) . ? Cu2 I2 2.5766(18) . ? Cu2 Cu2 2.583(2) 2_566 ? Cu2 I2 2.5928(13) 2_566 ? I2 Cu2 2.5928(13) 2_566 ? N60 C70 1.324(6) . ? N60 C72 1.369(6) . ? N61 C61 1.320(6) . ? N61 C71 1.374(6) . ? C61 C62 1.400(7) . ? C61 H61 0.9500 . ? C62 C63 1.374(7) . ? C62 H62 0.9500 . ? C63 C64 1.403(7) . ? C63 H63 0.9500 . ? C64 C71 1.402(7) . ? C64 C65 1.422(7) . ? C65 C66 1.347(8) . ? C65 H65 0.9500 . ? C66 C67 1.437(7) . ? C66 H66 0.9500 . ? C67 C68 1.391(7) . ? C67 C72 1.402(7) . ? C68 C69 1.361(8) . ? C68 H68 0.9500 . ? C69 C70 1.387(7) . ? C69 H69 0.9500 . ? C70 H70 0.9500 . ? C71 C72 1.420(7) . ? 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 N42 Cu1 N41 80.20(17) . . ? N42 Cu1 P1 132.79(13) . . ? N41 Cu1 P1 115.46(14) . . ? N42 Cu1 I1 107.06(13) . . ? N41 Cu1 I1 111.50(12) . . ? P1 Cu1 I1 107.06(5) . . ? C21 P1 C11 100.1(3) . . ? C21 P1 C31 101.9(3) . . ? C11 P1 C31 99.2(3) . . ? C21 P1 Cu1 106.92(19) . . ? C11 P1 Cu1 125.2(2) . . ? C31 P1 Cu1 119.8(3) . . ? N11 C11 P1 113.4(4) . . ? N11 C11 H11A 108.9 . . ? P1 C11 H11A 108.9 . . ? N11 C11 H11B 108.9 . . ? P1 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C11 N11 C12 114.0(5) . . ? C11 N11 C16 113.5(5) . . ? C12 N11 C16 104.7(5) . . ? N11 C12 C13 110.9(7) . . ? N11 C12 H12A 109.5 . . ? C13 C12 H12A 109.5 . . ? N11 C12 H12B 109.4 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 108.0 . . ? O14 C13 C12 111.6(6) . . ? O14 C13 H13A 109.3 . . ? C12 C13 H13A 109.3 . . ? O14 C13 H13B 109.3 . . ? C12 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? C13 O14 C15 107.5(6) . . ? O14 C15 C16 110.9(6) . . ? O14 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? O14 C15 H15B 109.5 . . ? C16 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? N11 C16 C15 110.8(7) . . ? N11 C16 H16A 109.5 . . ? C15 C16 H16A 109.5 . . ? N11 C16 H16B 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? N21 C21 P1 116.4(4) . . ? N21 C21 H21A 108.2 . . ? P1 C21 H21A 108.2 . . ? N21 C21 H21B 108.2 . . ? P1 C21 H21B 108.2 . . ? H21A C21 H21B 107.4 . . ? C26 N21 C22 108.9(6) . . ? C26 N21 C21 110.6(5) . . ? C22 N21 C21 112.9(5) . . ? N21 C22 C23 110.4(6) . . ? N21 C22 H22A 109.6 . . ? C23 C22 H22A 109.6 . . ? N21 C22 H22B 109.6 . . ? C23 C22 H22B 109.6 . . ? H22A C22 H22B 108.1 . . ? O24 C23 C22 111.1(7) . . ? O24 C23 H23A 109.4 . . ? C22 C23 H23A 109.4 . . ? O24 C23 H23B 109.4 . . ? C22 C23 H23B 109.4 . . ? H23A C23 H23B 108.0 . . ? C23 O24 C25 109.4(5) . . ? O24 C25 C26 109.6(6) . . ? O24 C25 H25A 109.8 . . ? C26 C25 H25A 109.8 . . ? O24 C25 H25B 109.8 . . ? C26 C25 H25B 109.8 . . ? H25A C25 H25B 108.2 . . ? N21 C26 C25 110.4(5) . . ? N21 C26 H26A 109.6 . . ? C25 C26 H26A 109.6 . . ? N21 C26 H26B 109.6 . . ? C25 C26 H26B 109.6 . . ? H26A C26 H26B 108.1 . . ? N31 C31 P1 111.8(5) . . ? N31 C31 H31A 109.3 . . ? P1 C31 H31A 109.3 . . ? N31 C31 H31B 109.3 . . ? P1 C31 H31B 109.2 . . ? H31A C31 H31B 107.9 . . ? C32 N31 C36 116.9(6) . . ? C32 N31 C31 115.1(6) . . ? C36 N31 C31 119.9(6) . . ? N31 C32 C33 118.0(6) . . ? N31 C32 H32A 107.8 . . ? C33 C32 H32A 107.8 . . ? N31 C32 H32B 107.8 . . ? C33 C32 H32B 107.8 . . ? H32A C32 H32B 107.2 . . ? O34 C33 C32 119.0(6) . . ? O34 C33 H33A 107.5 . . ? C32 C33 H33A 107.6 . . ? O34 C33 H33B 107.6 . . ? C32 C33 H33B 107.6 . . ? H33A C33 H33B 107.0 . . ? C35 O34 C33 117.3(6) . . ? O34 C35 C36 119.5(7) . . ? O34 C35 H35A 107.5 . . ? C36 C35 H35A 107.4 . . ? O34 C35 H35B 107.4 . . ? C36 C35 H35B 107.4 . . ? H35A C35 H35B 107.0 . . ? N31 C36 C35 114.9(7) . . ? N31 C36 H36A 108.6 . . ? C35 C36 H36A 108.6 . . ? N31 C36 H36B 108.5 . . ? C35 C36 H36B 108.6 . . ? H36A C36 H36B 107.5 . . ? C41 N41 C51 117.4(4) . . ? C41 N41 Cu1 129.8(4) . . ? C51 N41 Cu1 112.5(3) . . ? C50 N42 C52 116.8(5) . . ? C50 N42 Cu1 130.2(4) . . ? C52 N42 Cu1 112.9(3) . . ? N41 C41 C42 122.6(5) . . ? N41 C41 H41 118.7 . . ? C42 C41 H41 118.7 . . ? C43 C42 C41 119.6(5) . . ? C43 C42 H42 120.2 . . ? C41 C42 H42 120.2 . . ? C42 C43 C44 119.4(5) . . ? C42 C43 H43 120.3 . . ? C44 C43 H43 120.3 . . ? C51 C44 C43 116.4(5) . . ? C51 C44 C45 120.7(5) . . ? C43 C44 C45 122.9(5) . . ? C46 C45 C44 120.1(5) . . ? C46 C45 H45 120.0 . . ? C44 C45 H45 120.0 . . ? C45 C46 C47 122.6(5) . . ? C45 C46 H46 118.7 . . ? C47 C46 H46 118.7 . . ? C48 C47 C52 117.5(5) . . ? C48 C47 C46 124.3(5) . . ? C52 C47 C46 118.1(5) . . ? C49 C48 C47 120.0(5) . . ? C49 C48 H48 120.0 . . ? C47 C48 H48 120.0 . . ? C48 C49 C50 119.0(5) . . ? C48 C49 H49 120.5 . . ? C50 C49 H49 120.5 . . ? N42 C50 C49 123.4(5) . . ? N42 C50 H50 118.3 . . ? C49 C50 H50 118.3 . . ? N41 C51 C44 124.6(5) . . ? N41 C51 C52 116.2(4) . . ? C44 C51 C52 119.1(5) . . ? N42 C52 C47 123.1(5) . . ? N42 C52 C51 117.5(5) . . ? C47 C52 C51 119.4(4) . . ? N61 Cu2 N60 80.80(16) . . ? N61 Cu2 I2 114.46(12) . . ? N60 Cu2 I2 112.49(12) . . ? N61 Cu2 Cu2 139.25(12) . 2_566 ? N60 Cu2 Cu2 139.89(12) . 2_566 ? I2 Cu2 Cu2 60.34(5) . 2_566 ? N61 Cu2 I2 110.07(11) . 2_566 ? N60 Cu2 I2 112.44(11) . 2_566 ? I2 Cu2 I2 120.05(5) . 2_566 ? Cu2 Cu2 I2 59.71(5) 2_566 2_566 ? Cu2 I2 Cu2 59.95(5) . 2_566 ? C70 N60 C72 117.2(4) . . ? C70 N60 Cu2 130.8(4) . . ? C72 N60 Cu2 111.9(3) . . ? C61 N61 C71 118.2(4) . . ? C61 N61 Cu2 130.1(3) . . ? C71 N61 Cu2 111.7(3) . . ? N61 C61 C62 123.5(5) . . ? N61 C61 H61 118.3 . . ? C62 C61 H61 118.3 . . ? C63 C62 C61 118.3(5) . . ? C63 C62 H62 120.9 . . ? C61 C62 H62 120.9 . . ? C62 C63 C64 120.5(5) . . ? C62 C63 H63 119.7 . . ? C64 C63 H63 119.7 . . ? C71 C64 C63 117.2(5) . . ? C71 C64 C65 119.7(5) . . ? C63 C64 C65 123.1(5) . . ? C66 C65 C64 120.6(5) . . ? C66 C65 H65 119.7 . . ? C64 C65 H65 119.7 . . ? C65 C66 C67 121.3(5) . . ? C65 C66 H66 119.3 . . ? C67 C66 H66 119.3 . . ? C68 C67 C72 117.4(5) . . ? C68 C67 C66 124.0(5) . . ? C72 C67 C66 118.5(5) . . ? C69 C68 C67 120.8(5) . . ? C69 C68 H68 119.6 . . ? C67 C68 H68 119.6 . . ? C68 C69 C70 117.9(5) . . ? C68 C69 H69 121.0 . . ? C70 C69 H69 121.0 . . ? N60 C70 C69 124.4(5) . . ? N60 C70 H70 117.8 . . ? C69 C70 H70 117.8 . . ? N61 C71 C64 122.4(5) . . ? N61 C71 C72 117.9(4) . . ? C64 C71 C72 119.6(5) . . ? N60 C72 C67 122.2(5) . . ? N60 C72 C71 117.6(4) . . ? C67 C72 C71 120.2(5) . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.924 _refine_diff_density_max 0.683 _refine_diff_density_min -0.492 _refine_diff_density_rms 0.105 # start Validation Reply Form _vrf_PLAT029_s31 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.92 RESPONSE: the crystal used for data collection was cut from a bigger one, and was not of good quality. ; _vrf_PLAT220_s31 ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.94 Ratio RESPONSE: small size of the crystal along with not good quality of data collection resulted in no satisfactory solution of the problem. ; # Attachment '- star8_NJ-ART-11-2009-000636_R2.cif' data_star8 _database_code_depnum_ccdc_archive 'CCDC 747839' #TrackingRef '- star8_NJ-ART-11-2009-000636_R2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'tris(morpholinomethyl)phosphine' ; _chemical_name_common tris(morpholinomethyl)phosphine _chemical_melting_point ? _chemical_formula_moiety 'C15 H30 N3 O3 P' _chemical_formula_sum 'C15 H30 N3 O3 P' _chemical_formula_weight 331.39 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 9.284(4) _cell_length_b 20.925(5) _cell_length_c 10.092(3) _cell_angle_alpha 90.00 _cell_angle_beta 118.76(3) _cell_angle_gamma 90.00 _cell_volume 1718.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1810 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 25.10 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.176 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.878 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details 'Oxford Diffraction, CrysAlis 1.171.30' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KM4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10992 _diffrn_reflns_av_R_equivalents 0.0819 _diffrn_reflns_av_sigmaI/netI 0.0875 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 25.10 _reflns_number_total 3045 _reflns_number_gt 1874 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, date)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, date)' _computing_data_reduction 'CrysAlis RED ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXL-97 _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^)+(0.0525P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3045 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1016 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1115 _refine_ls_wR_factor_gt 0.0960 _refine_ls_goodness_of_fit_ref 0.947 _refine_ls_restrained_S_all 0.947 _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 P1 P 0.56072(10) 0.72221(4) 0.05257(8) 0.0228(2) Uani 1 1 d . . . C11 C 0.4014(3) 0.67829(13) -0.1098(3) 0.0244(7) Uani 1 1 d . . . H11A H 0.2967 0.7023 -0.1516 0.029 Uiso 1 1 calc R . . H11B H 0.4339 0.6751 -0.1897 0.029 Uiso 1 1 calc R . . N11 N 0.3763(3) 0.61401(11) -0.0676(2) 0.0227(6) Uani 1 1 d . . . C12 C 0.2878(4) 0.61684(13) 0.0195(3) 0.0275(7) Uani 1 1 d . . . H12A H 0.1801 0.6379 -0.0414 0.033 Uiso 1 1 calc R . . H12B H 0.3515 0.6425 0.1122 0.033 Uiso 1 1 calc R . . C13 C 0.2624(4) 0.55061(13) 0.0616(3) 0.0300(8) Uani 1 1 d . . . H13A H 0.3705 0.5304 0.1258 0.036 Uiso 1 1 calc R . . H13B H 0.2033 0.5531 0.1210 0.036 Uiso 1 1 calc R . . O14 O 0.1709(2) 0.51225(9) -0.0686(2) 0.0303(5) Uani 1 1 d . . . C15 C 0.2540(4) 0.50889(14) -0.1558(3) 0.0324(8) Uani 1 1 d . . . H15B H 0.1880 0.4831 -0.2477 0.039 Uiso 1 1 calc R . . H15A H 0.3611 0.4873 -0.0961 0.039 Uiso 1 1 calc R . . C16 C 0.2818(4) 0.57402(13) -0.2008(3) 0.0284(7) Uani 1 1 d . . . H16B H 0.3418 0.5701 -0.2592 0.034 Uiso 1 1 calc R . . H16A H 0.1745 0.5945 -0.2666 0.034 Uiso 1 1 calc R . . C21 C 0.7464(3) 0.68389(14) 0.0642(3) 0.0240(7) Uani 1 1 d . . . H21A H 0.7138 0.6438 0.0047 0.029 Uiso 1 1 calc R . . H21B H 0.7946 0.7127 0.0181 0.029 Uiso 1 1 calc R . . N21 N 0.8712(3) 0.66925(11) 0.2191(2) 0.0217(5) Uani 1 1 d . . . C22 C 1.0053(3) 0.63230(13) 0.2211(3) 0.0249(7) Uani 1 1 d . . . H22A H 1.0591 0.6574 0.1740 0.030 Uiso 1 1 calc R . . H22B H 0.9616 0.5925 0.1622 0.030 Uiso 1 1 calc R . . C23 C 1.1286(4) 0.61617(13) 0.3817(3) 0.0275(7) Uani 1 1 d . . . H23A H 1.0753 0.5891 0.4262 0.033 Uiso 1 1 calc R . . H23B H 1.2196 0.5913 0.3824 0.033 Uiso 1 1 calc R . . O24 O 1.1933(2) 0.67197(9) 0.4718(2) 0.0279(5) Uani 1 1 d . . . C25 C 1.0631(4) 0.70906(13) 0.4682(3) 0.0263(7) Uani 1 1 d . . . H25B H 1.1088 0.7484 0.5284 0.032 Uiso 1 1 calc R . . H25A H 1.0082 0.6844 0.5150 0.032 Uiso 1 1 calc R . . C26 C 0.9385(3) 0.72694(13) 0.3092(3) 0.0231(7) Uani 1 1 d . . . H26B H 0.8489 0.7521 0.3105 0.028 Uiso 1 1 calc R . . H26A H 0.9912 0.7537 0.2636 0.028 Uiso 1 1 calc R . . C31 C 0.5457(4) 0.79552(12) -0.0546(3) 0.0237(7) Uani 1 1 d . . . H31B H 0.5614 0.7842 -0.1421 0.028 Uiso 1 1 calc R . . H31A H 0.4339 0.8135 -0.0944 0.028 Uiso 1 1 calc R . . N31 N 0.6654(3) 0.84436(10) 0.0347(2) 0.0218(6) Uani 1 1 d . . . C32 C 0.6387(4) 0.86858(13) 0.1571(3) 0.0252(7) Uani 1 1 d . . . H32B H 0.6454 0.8329 0.2244 0.030 Uiso 1 1 calc R . . H32A H 0.5278 0.8878 0.1146 0.030 Uiso 1 1 calc R . . C33 C 0.7660(4) 0.91782(13) 0.2458(3) 0.0316(8) Uani 1 1 d . . . H33B H 0.7499 0.9329 0.3308 0.038 Uiso 1 1 calc R . . H33A H 0.8765 0.8983 0.2886 0.038 Uiso 1 1 calc R . . O34 O 0.7564(3) 0.97096(9) 0.1531(2) 0.0356(6) Uani 1 1 d . . . C35 C 0.7799(4) 0.94826(14) 0.0312(3) 0.0323(8) Uani 1 1 d . . . H35A H 0.8917 0.9300 0.0725 0.039 Uiso 1 1 calc R . . H35B H 0.7715 0.9847 -0.0349 0.039 Uiso 1 1 calc R . . C36 C 0.6560(4) 0.89832(13) -0.0613(3) 0.0278(7) Uani 1 1 d . . . H36A H 0.5442 0.9170 -0.1083 0.033 Uiso 1 1 calc R . . H36B H 0.6776 0.8833 -0.1431 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0269(4) 0.0264(4) 0.0171(4) 0.0002(4) 0.0121(3) -0.0024(4) C11 0.0262(17) 0.0300(18) 0.0183(15) 0.0021(13) 0.0118(14) -0.0021(14) N11 0.0301(14) 0.0243(14) 0.0182(13) -0.0015(11) 0.0152(12) -0.0044(12) C12 0.0368(19) 0.0299(18) 0.0222(16) -0.0040(14) 0.0194(15) -0.0025(15) C13 0.045(2) 0.0287(17) 0.0256(17) -0.0060(14) 0.0239(16) -0.0056(16) O14 0.0396(13) 0.0297(12) 0.0286(11) -0.0075(10) 0.0220(11) -0.0114(10) C15 0.045(2) 0.0345(18) 0.0298(17) -0.0089(15) 0.0275(16) -0.0088(16) C16 0.0357(19) 0.0329(18) 0.0208(16) -0.0060(14) 0.0170(15) -0.0096(15) C21 0.0299(18) 0.0283(17) 0.0165(15) -0.0014(13) 0.0133(14) 0.0004(14) N21 0.0250(14) 0.0228(13) 0.0160(12) -0.0017(11) 0.0087(11) 0.0007(12) C22 0.0301(18) 0.0234(16) 0.0268(16) -0.0032(14) 0.0182(15) -0.0024(14) C23 0.0297(18) 0.0259(17) 0.0294(17) -0.0007(14) 0.0162(15) 0.0013(15) O24 0.0277(12) 0.0295(12) 0.0229(11) -0.0036(9) 0.0093(10) 0.0000(10) C25 0.0285(18) 0.0272(18) 0.0224(16) -0.0020(13) 0.0117(14) 0.0038(14) C26 0.0276(17) 0.0230(16) 0.0222(15) -0.0035(14) 0.0148(14) -0.0001(14) C31 0.0312(18) 0.0279(17) 0.0162(14) -0.0008(13) 0.0149(14) 0.0005(14) N31 0.0315(14) 0.0208(13) 0.0160(12) -0.0020(11) 0.0137(11) -0.0027(11) C32 0.0331(18) 0.0248(17) 0.0195(15) 0.0008(13) 0.0142(14) 0.0027(14) C33 0.050(2) 0.0249(17) 0.0197(16) 0.0023(14) 0.0170(16) 0.0007(16) O34 0.0612(16) 0.0250(11) 0.0245(11) -0.0013(9) 0.0238(12) -0.0039(11) C35 0.046(2) 0.0293(18) 0.0273(17) 0.0022(15) 0.0225(17) -0.0034(16) C36 0.0400(19) 0.0257(16) 0.0216(16) -0.0005(14) 0.0179(15) 0.0002(15) _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 P1 C11 1.840(3) . ? P1 C31 1.843(3) . ? P1 C21 1.853(3) . ? C11 N11 1.463(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? N11 C16 1.464(3) . ? N11 C12 1.465(3) . ? C12 C13 1.501(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 O14 1.421(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? O14 C15 1.424(3) . ? C15 C16 1.498(4) . ? C15 H15B 0.9900 . ? C15 H15A 0.9900 . ? C16 H16B 0.9900 . ? C16 H16A 0.9900 . ? C21 N21 1.462(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? N21 C22 1.457(3) . ? N21 C26 1.458(3) . ? C22 C23 1.505(4) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 O24 1.423(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? O24 C25 1.423(3) . ? C25 C26 1.506(4) . ? C25 H25B 0.9900 . ? C25 H25A 0.9900 . ? C26 H26B 0.9900 . ? C26 H26A 0.9900 . ? C31 N31 1.458(3) . ? C31 H31B 0.9900 . ? C31 H31A 0.9900 . ? N31 C36 1.463(3) . ? N31 C32 1.463(3) . ? C32 C33 1.497(4) . ? C32 H32B 0.9900 . ? C32 H32A 0.9900 . ? C33 O34 1.428(3) . ? C33 H33B 0.9900 . ? C33 H33A 0.9900 . ? O34 C35 1.430(3) . ? C35 C36 1.501(4) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 P1 C31 95.27(12) . . ? C11 P1 C21 99.50(13) . . ? C31 P1 C21 101.70(13) . . ? N11 C11 P1 111.85(18) . . ? N11 C11 H11A 109.2 . . ? P1 C11 H11A 109.2 . . ? N11 C11 H11B 109.2 . . ? P1 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? C11 N11 C16 111.5(2) . . ? C11 N11 C12 110.6(2) . . ? C16 N11 C12 108.2(2) . . ? N11 C12 C13 110.0(2) . . ? N11 C12 H12A 109.7 . . ? C13 C12 H12A 109.7 . . ? N11 C12 H12B 109.7 . . ? C13 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? O14 C13 C12 111.4(2) . . ? O14 C13 H13A 109.3 . . ? C12 C13 H13A 109.3 . . ? O14 C13 H13B 109.3 . . ? C12 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? C13 O14 C15 109.8(2) . . ? O14 C15 C16 111.5(2) . . ? O14 C15 H15B 109.3 . . ? C16 C15 H15B 109.3 . . ? O14 C15 H15A 109.3 . . ? C16 C15 H15A 109.3 . . ? H15B C15 H15A 108.0 . . ? N11 C16 C15 110.9(2) . . ? N11 C16 H16B 109.5 . . ? C15 C16 H16B 109.5 . . ? N11 C16 H16A 109.5 . . ? C15 C16 H16A 109.5 . . ? H16B C16 H16A 108.1 . . ? N21 C21 P1 113.16(17) . . ? N21 C21 H21A 108.9 . . ? P1 C21 H21A 108.9 . . ? N21 C21 H21B 108.9 . . ? P1 C21 H21B 108.9 . . ? H21A C21 H21B 107.8 . . ? C22 N21 C26 108.9(2) . . ? C22 N21 C21 111.0(2) . . ? C26 N21 C21 112.0(2) . . ? N21 C22 C23 109.6(2) . . ? N21 C22 H22A 109.7 . . ? C23 C22 H22A 109.7 . . ? N21 C22 H22B 109.7 . . ? C23 C22 H22B 109.7 . . ? H22A C22 H22B 108.2 . . ? O24 C23 C22 111.9(2) . . ? O24 C23 H23A 109.2 . . ? C22 C23 H23A 109.2 . . ? O24 C23 H23B 109.2 . . ? C22 C23 H23B 109.2 . . ? H23A C23 H23B 107.9 . . ? C25 O24 C23 109.8(2) . . ? O24 C25 C26 111.7(2) . . ? O24 C25 H25B 109.3 . . ? C26 C25 H25B 109.3 . . ? O24 C25 H25A 109.3 . . ? C26 C25 H25A 109.3 . . ? H25B C25 H25A 107.9 . . ? N21 C26 C25 109.7(2) . . ? N21 C26 H26B 109.7 . . ? C25 C26 H26B 109.7 . . ? N21 C26 H26A 109.7 . . ? C25 C26 H26A 109.7 . . ? H26B C26 H26A 108.2 . . ? N31 C31 P1 113.63(18) . . ? N31 C31 H31B 108.8 . . ? P1 C31 H31B 108.8 . . ? N31 C31 H31A 108.8 . . ? P1 C31 H31A 108.8 . . ? H31B C31 H31A 107.7 . . ? C31 N31 C36 110.3(2) . . ? C31 N31 C32 112.1(2) . . ? C36 N31 C32 108.2(2) . . ? N31 C32 C33 109.7(2) . . ? N31 C32 H32B 109.7 . . ? C33 C32 H32B 109.7 . . ? N31 C32 H32A 109.7 . . ? C33 C32 H32A 109.7 . . ? H32B C32 H32A 108.2 . . ? O34 C33 C32 111.2(2) . . ? O34 C33 H33B 109.4 . . ? C32 C33 H33B 109.4 . . ? O34 C33 H33A 109.4 . . ? C32 C33 H33A 109.4 . . ? H33B C33 H33A 108.0 . . ? C33 O34 C35 108.5(2) . . ? O34 C35 C36 112.2(2) . . ? O34 C35 H35A 109.2 . . ? C36 C35 H35A 109.2 . . ? O34 C35 H35B 109.2 . . ? C36 C35 H35B 109.2 . . ? H35A C35 H35B 107.9 . . ? N31 C36 C35 110.0(2) . . ? N31 C36 H36A 109.7 . . ? C35 C36 H36A 109.7 . . ? N31 C36 H36B 109.7 . . ? C35 C36 H36B 109.7 . . ? H36A C36 H36B 108.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C31 P1 C11 N11 179.9(2) . . . . ? C21 P1 C11 N11 77.1(2) . . . . ? P1 C11 N11 C16 -165.75(19) . . . . ? P1 C11 N11 C12 73.8(2) . . . . ? C11 N11 C12 C13 179.8(2) . . . . ? C16 N11 C12 C13 57.4(3) . . . . ? N11 C12 C13 O14 -59.5(3) . . . . ? C12 C13 O14 C15 58.4(3) . . . . ? C13 O14 C15 C16 -57.4(3) . . . . ? C11 N11 C16 C15 -178.7(2) . . . . ? C12 N11 C16 C15 -56.9(3) . . . . ? O14 C15 C16 N11 57.9(3) . . . . ? C11 P1 C21 N21 -137.3(2) . . . . ? C31 P1 C21 N21 125.2(2) . . . . ? P1 C21 N21 C22 173.00(18) . . . . ? P1 C21 N21 C26 -65.1(3) . . . . ? C26 N21 C22 C23 58.2(3) . . . . ? C21 N21 C22 C23 -178.1(2) . . . . ? N21 C22 C23 O24 -58.6(3) . . . . ? C22 C23 O24 C25 57.2(3) . . . . ? C23 O24 C25 C26 -57.2(3) . . . . ? C22 N21 C26 C25 -58.2(3) . . . . ? C21 N21 C26 C25 178.6(2) . . . . ? O24 C25 C26 N21 58.5(3) . . . . ? C11 P1 C31 N31 -176.3(2) . . . . ? C21 P1 C31 N31 -75.4(2) . . . . ? P1 C31 N31 C36 174.69(18) . . . . ? P1 C31 N31 C32 -64.7(3) . . . . ? C31 N31 C32 C33 179.3(2) . . . . ? C36 N31 C32 C33 -58.9(3) . . . . ? N31 C32 C33 O34 61.2(3) . . . . ? C32 C33 O34 C35 -59.1(3) . . . . ? C33 O34 C35 C36 57.8(3) . . . . ? C31 N31 C36 C35 -179.8(2) . . . . ? C32 N31 C36 C35 57.3(3) . . . . ? O34 C35 C36 N31 -58.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C23 H23B O34 0.99 2.57 3.295(4) 130 2_745 C22 H22B O14 0.99 2.47 3.431(4) 164 3_665 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.306 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.059 #_publ_author_letter #; #Please consider this CIF as deposit in the Cambridge #Crystallographic Data Centre #; #================================================ # Attachment 'star15a.cif' data_star15a _database_code_depnum_ccdc_archive 'CCDC 747840' #TrackingRef 'star15a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Iodo-(1,10-phenanthroline-N,N')- (tris((4-methylpiperazin-1-yl)methyl) phosphine-P)-copper(I) toluene solvate' ; _chemical_name_common ; 'Iodo-(1,10-phenanthroline-N,N')-(tris((4-methylpiperazin-1-yl)methyl) phosphine- P)- copper(i) toluene solvate' ; _chemical_melting_point ? _chemical_formula_moiety 'C30 H47 Cu I N8 P, C7 H8' _chemical_formula_sum 'C37 H55 Cu I N8 P' _chemical_formula_weight 833.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' 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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.799(3) _cell_length_b 18.400(4) _cell_length_c 19.828(3) _cell_angle_alpha 64.78(4) _cell_angle_beta 71.94(5) _cell_angle_gamma 86.62(3) _cell_volume 4002(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2624 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 25.20 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1720 _exptl_absorpt_coefficient_mu 1.393 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.678 _exptl_absorpt_correction_T_max 0.876 _exptl_absorpt_process_details 'Oxford Diffraction, CrysAlis RED 1.171.30' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KM4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 48915 _diffrn_reflns_av_R_equivalents 0.1098 _diffrn_reflns_av_sigmaI/netI 0.1118 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 25.10 _reflns_number_total 14193 _reflns_number_gt 8624 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, date)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, date)' _computing_data_reduction 'CrysAlis RED ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXL-97 _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^)+(0.0000P)^2^+159.3083P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 14193 _refine_ls_number_parameters 860 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1518 _refine_ls_R_factor_gt 0.0984 _refine_ls_wR_factor_ref 0.2704 _refine_ls_wR_factor_gt 0.2529 _refine_ls_goodness_of_fit_ref 1.143 _refine_ls_restrained_S_all 1.143 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1A Cu -0.26173(15) 0.13060(11) 0.26349(11) 0.0258(4) Uani 1 1 d . . . I1A I -0.25407(8) 0.11413(6) 0.39953(6) 0.0278(3) Uani 1 1 d . . . P1A P -0.1973(3) 0.0185(2) 0.2581(2) 0.0303(10) Uani 1 1 d . . . C11A C -0.2846(15) -0.0690(10) 0.3417(12) 0.048(5) Uani 1 1 d . . . H11A H -0.2778 -0.0708 0.3908 0.058 Uiso 1 1 calc R . . H11E H -0.3625 -0.0612 0.3436 0.058 Uiso 1 1 calc R . . N11A N -0.2586(12) -0.1454(8) 0.3396(9) 0.040(4) Uani 1 1 d . . . C12A C -0.3429(14) -0.1796(10) 0.3245(10) 0.040(4) Uani 1 1 d . . . H12A H -0.3580 -0.1391 0.2769 0.048 Uiso 1 1 calc R . . H12E H -0.4118 -0.1933 0.3692 0.048 Uiso 1 1 calc R . . C13A C -0.3085(15) -0.2539(9) 0.3129(10) 0.037(4) Uani 1 1 d . . . H13A H -0.3693 -0.2770 0.3051 0.045 Uiso 1 1 calc R . . H13E H -0.2436 -0.2394 0.2652 0.045 Uiso 1 1 calc R . . N14A N -0.2811(12) -0.3137(8) 0.3805(9) 0.040(4) Uani 1 1 d . . . C15A C -0.1955(14) -0.2791(9) 0.3953(10) 0.035(4) Uani 1 1 d . . . H15A H -0.1277 -0.2627 0.3493 0.041 Uiso 1 1 calc R . . H15E H -0.1776 -0.3199 0.4415 0.041 Uiso 1 1 calc R . . C16A C -0.2352(14) -0.2066(10) 0.4101(10) 0.036(4) Uani 1 1 d . . . H16A H -0.3028 -0.2229 0.4562 0.044 Uiso 1 1 calc R . . H16E H -0.1779 -0.1838 0.4214 0.044 Uiso 1 1 calc R . . C17A C -0.2451(16) -0.3851(10) 0.3666(11) 0.046(5) Uani 1 1 d . . . H17A H -0.1788 -0.3695 0.3206 0.069 Uiso 1 1 calc R . . H17E H -0.3040 -0.4075 0.3572 0.069 Uiso 1 1 calc R . . H17F H -0.2285 -0.4258 0.4127 0.069 Uiso 1 1 calc R . . C21A C -0.1819(15) -0.0080(10) 0.1764(10) 0.039(4) Uani 1 1 d . . . H21A H -0.1138 0.0214 0.1335 0.047 Uiso 1 1 calc R . . H21E H -0.1727 -0.0664 0.1945 0.047 Uiso 1 1 calc R . . N21A N -0.2726(13) 0.0098(8) 0.1454(8) 0.039(4) Uani 1 1 d . . . C22A C -0.2698(17) -0.0360(10) 0.0996(11) 0.048(5) Uani 1 1 d . . . H22A H -0.2773 -0.0945 0.1341 0.057 Uiso 1 1 calc R . . H22E H -0.1983 -0.0229 0.0572 0.057 Uiso 1 1 calc R . . C23A C -0.362(3) -0.0152(13) 0.0649(14) 0.081(9) Uani 1 1 d . . . H23A H -0.3598 -0.0465 0.0344 0.097 Uiso 1 1 calc R . . H23E H -0.4332 -0.0301 0.1075 0.097 Uiso 1 1 calc R . . N24A N -0.352(3) 0.0688(13) 0.0147(14) 0.140(13) Uani 1 1 d . . . C25A C -0.357(3) 0.1156(14) 0.0599(15) 0.089(10) Uani 1 1 d . . . H25A H -0.3486 0.1740 0.0248 0.107 Uiso 1 1 calc R . . H25E H -0.4296 0.1032 0.1014 0.107 Uiso 1 1 calc R . . C26A C -0.270(2) 0.0951(11) 0.0948(11) 0.070(8) Uani 1 1 d . . . H26A H -0.2748 0.1260 0.1259 0.084 Uiso 1 1 calc R . . H26E H -0.1985 0.1122 0.0523 0.084 Uiso 1 1 calc R . . C27A C -0.398(3) 0.0937(15) -0.0387(16) 0.103(11) Uani 1 1 d . . . H27A H -0.3767 0.1515 -0.0714 0.154 Uiso 1 1 calc R . . H27E H -0.4779 0.0845 -0.0148 0.154 Uiso 1 1 calc R . . H27F H -0.3729 0.0644 -0.0713 0.154 Uiso 1 1 calc R . . C31A C -0.0608(13) -0.0068(9) 0.2737(11) 0.038(4) Uani 1 1 d . . . H31A H -0.0570 0.0054 0.3170 0.046 Uiso 1 1 calc R . . H31E H -0.0552 -0.0655 0.2904 0.046 Uiso 1 1 calc R . . N31A N 0.0329(11) 0.0365(8) 0.2045(8) 0.039(4) Uani 1 1 d . . . C32A C 0.1377(15) 0.0077(10) 0.2148(11) 0.052(6) Uani 1 1 d . . . H32A H 0.1356 -0.0512 0.2310 0.062 Uiso 1 1 calc R . . H32E H 0.1504 0.0181 0.2569 0.062 Uiso 1 1 calc R . . C33A C 0.2296(15) 0.0492(10) 0.1403(11) 0.045(5) Uani 1 1 d . . . H33A H 0.3000 0.0273 0.1472 0.054 Uiso 1 1 calc R . . H33E H 0.2166 0.0397 0.0979 0.054 Uiso 1 1 calc R . . N34A N 0.2361(11) 0.1363(8) 0.1188(8) 0.035(3) Uani 1 1 d . . . C35A C 0.1314(12) 0.1655(10) 0.1090(10) 0.035(4) Uani 1 1 d . . . H35A H 0.1208 0.1579 0.0649 0.042 Uiso 1 1 calc R . . H35E H 0.1339 0.2240 0.0948 0.042 Uiso 1 1 calc R . . C36A C 0.0352(13) 0.1239(9) 0.1807(11) 0.038(4) Uani 1 1 d . . . H36A H 0.0409 0.1356 0.2238 0.045 Uiso 1 1 calc R . . H36E H -0.0340 0.1440 0.1697 0.045 Uiso 1 1 calc R . . C37A C 0.3256(14) 0.1779(12) 0.0459(12) 0.054(6) Uani 1 1 d . . . H37A H 0.3122 0.1690 0.0038 0.082 Uiso 1 1 calc R . . H37E H 0.3956 0.1568 0.0528 0.082 Uiso 1 1 calc R . . H37F H 0.3293 0.2357 0.0320 0.082 Uiso 1 1 calc R . . N41A N -0.4103(10) 0.1589(7) 0.2386(7) 0.025(3) Uani 1 1 d . . . N42A N -0.2180(10) 0.2496(8) 0.1817(7) 0.025(3) Uani 1 1 d . . . C41A C -0.5052(12) 0.1140(9) 0.2664(9) 0.027(4) Uani 1 1 d . . . H41A H -0.5124 0.0614 0.3076 0.032 Uiso 1 1 calc R . . C42A C -0.5961(13) 0.1403(9) 0.2381(9) 0.031(4) Uani 1 1 d . . . H42A H -0.6619 0.1058 0.2598 0.037 Uiso 1 1 calc R . . C43A C -0.5877(13) 0.2159(10) 0.1791(9) 0.033(4) Uani 1 1 d . . . H43A H -0.6478 0.2352 0.1596 0.040 Uiso 1 1 calc R . . C44A C -0.4878(13) 0.2649(10) 0.1477(9) 0.030(4) Uani 1 1 d . . . C45A C -0.4724(12) 0.3457(9) 0.0849(9) 0.030(4) Uani 1 1 d . . . H45A H -0.5278 0.3654 0.0604 0.036 Uiso 1 1 calc R . . C46A C -0.3716(13) 0.3966(10) 0.0592(9) 0.030(4) Uiso 1 1 d . . . H46A H -0.3648 0.4519 0.0234 0.036 Uiso 1 1 calc R . . C47A C -0.2872(12) 0.3632(8) 0.0877(8) 0.023(3) Uani 1 1 d . . . C48A C -0.1857(12) 0.4074(9) 0.0626(10) 0.033(4) Uani 1 1 d . . . H48A H -0.1717 0.4601 0.0208 0.039 Uiso 1 1 calc R . . C49A C -0.1070(14) 0.3750(9) 0.0978(9) 0.032(4) Uani 1 1 d . . . H49A H -0.0401 0.4058 0.0830 0.039 Uiso 1 1 calc R . . C50A C -0.1268(13) 0.2958(8) 0.1559(9) 0.027(4) Uani 1 1 d . . . H50A H -0.0701 0.2738 0.1784 0.033 Uiso 1 1 calc R . . C51A C -0.4008(12) 0.2341(9) 0.1783(8) 0.021(3) Uani 1 1 d . . . C52A C -0.2989(12) 0.2846(9) 0.1485(9) 0.030(4) Uani 1 1 d . . . Cu1B Cu 0.17538(15) 0.36997(11) 0.25370(11) 0.0278(5) Uani 1 1 d . . . I1B I 0.19523(8) 0.37844(6) 0.11498(6) 0.0293(3) Uani 1 1 d . . . P1B P 0.0867(3) 0.4756(2) 0.2550(2) 0.0248(9) Uani 1 1 d . . . C11B C 0.1641(13) 0.5659(9) 0.1685(9) 0.031(4) Uani 1 1 d . . . H11B H 0.2370 0.5731 0.1734 0.037 Uiso 1 1 calc R . . H11G H 0.1771 0.5565 0.1210 0.037 Uiso 1 1 calc R . . N11B N 0.1094(10) 0.6410(7) 0.1570(8) 0.031(3) Uani 1 1 d . . . C12B C 0.1706(14) 0.6996(10) 0.1647(11) 0.041(4) Uani 1 1 d . . . H12B H 0.2408 0.7188 0.1208 0.049 Uiso 1 1 calc R . . H12G H 0.1885 0.6736 0.2145 0.049 Uiso 1 1 calc R . . C13B C 0.1045(17) 0.7708(11) 0.1641(11) 0.052(5) Uani 1 1 d . . . H13B H 0.0370 0.7526 0.2103 0.062 Uiso 1 1 calc R . . H13G H 0.1488 0.8110 0.1671 0.062 Uiso 1 1 calc R . . N14B N 0.0747(12) 0.8072(9) 0.0931(9) 0.043(4) Uani 1 1 d . . . C15B C 0.0165(16) 0.7483(12) 0.0828(13) 0.051(5) Uani 1 1 d . . . H15B H 0.0005 0.7748 0.0323 0.062 Uiso 1 1 calc R . . H15G H -0.0546 0.7281 0.1257 0.062 Uiso 1 1 calc R . . C16B C 0.0843(14) 0.6791(11) 0.0834(10) 0.039(4) Uani 1 1 d . . . H16B H 0.0432 0.6393 0.0776 0.047 Uiso 1 1 calc R . . H16G H 0.1537 0.6986 0.0388 0.047 Uiso 1 1 calc R . . C17B C 0.0093(18) 0.8758(12) 0.0910(14) 0.075(8) Uani 1 1 d . . . H17B H -0.0610 0.8567 0.1337 0.112 Uiso 1 1 calc R . . H17G H -0.0048 0.9020 0.0405 0.112 Uiso 1 1 calc R . . H17H H 0.0500 0.9145 0.0976 0.112 Uiso 1 1 calc R . . C21B C 0.0593(13) 0.5114(9) 0.3307(10) 0.033(4) Uani 1 1 d . . . H21B H 0.0253 0.5632 0.3139 0.040 Uiso 1 1 calc R . . H21G H 0.0062 0.4720 0.3797 0.040 Uiso 1 1 calc R . . N21B N 0.1602(10) 0.5226(8) 0.3460(7) 0.028(3) Uani 1 1 d . . . C22B C 0.1514(14) 0.5769(10) 0.3852(10) 0.035(4) Uani 1 1 d . . . H22B H 0.0979 0.5518 0.4389 0.042 Uiso 1 1 calc R . . H22G H 0.1253 0.6288 0.3552 0.042 Uiso 1 1 calc R . . C23B C 0.2643(15) 0.5911(12) 0.3892(12) 0.047(5) Uani 1 1 d . . . H23B H 0.3164 0.6175 0.3352 0.056 Uiso 1 1 calc R . . H23G H 0.2598 0.6282 0.4142 0.056 Uiso 1 1 calc R . . N24B N 0.3060(12) 0.5183(9) 0.4324(9) 0.043(4) Uani 1 1 d . . . C25B C 0.3067(15) 0.4592(11) 0.4002(10) 0.041(4) Uani 1 1 d . . . H25B H 0.3282 0.4073 0.4344 0.049 Uiso 1 1 calc R . . H25G H 0.3624 0.4787 0.3474 0.049 Uiso 1 1 calc R . . C26B C 0.1950(13) 0.4457(10) 0.3941(10) 0.034(4) Uani 1 1 d . . . H26B H 0.1993 0.4078 0.3701 0.041 Uiso 1 1 calc R . . H26G H 0.1402 0.4216 0.4473 0.041 Uiso 1 1 calc R . . C27B C 0.4171(16) 0.5336(15) 0.4318(14) 0.064(7) Uani 1 1 d . . . H27B H 0.4425 0.4831 0.4636 0.095 Uiso 1 1 calc R . . H27G H 0.4161 0.5725 0.4536 0.095 Uiso 1 1 calc R . . H27H H 0.4672 0.5555 0.3776 0.095 Uiso 1 1 calc R . . C31B C -0.0496(12) 0.4814(10) 0.2415(9) 0.030(4) Uani 1 1 d . . . H31B H -0.0640 0.5388 0.2173 0.036 Uiso 1 1 calc R . . H31G H -0.0486 0.4583 0.2044 0.036 Uiso 1 1 calc R . . N31B N -0.1380(9) 0.4401(7) 0.3128(8) 0.026(3) Uani 1 1 d . . . C32B C -0.2459(12) 0.4542(9) 0.3021(10) 0.027(4) Uani 1 1 d . . . H32B H -0.2525 0.4328 0.2654 0.033 Uiso 1 1 calc R . . H32G H -0.2529 0.5129 0.2783 0.033 Uiso 1 1 calc R . . C33B C -0.3376(13) 0.4151(9) 0.3780(10) 0.029(4) Uani 1 1 d . . . H33B H -0.3322 0.4366 0.4149 0.035 Uiso 1 1 calc R . . H33G H -0.4095 0.4272 0.3686 0.035 Uiso 1 1 calc R . . N34B N -0.3302(10) 0.3279(7) 0.4121(8) 0.030(3) Uani 1 1 d . . . C35B C -0.2223(12) 0.3114(10) 0.4241(9) 0.030(4) Uani 1 1 d . . . H35B H -0.2164 0.2525 0.4468 0.036 Uiso 1 1 calc R . . H35G H -0.2155 0.3313 0.4619 0.036 Uiso 1 1 calc R . . C36B C -0.1312(12) 0.3511(8) 0.3489(9) 0.028(4) Uani 1 1 d . . . H36B H -0.1355 0.3291 0.3121 0.033 Uiso 1 1 calc R . . H36G H -0.0595 0.3393 0.3587 0.033 Uiso 1 1 calc R . . C37B C -0.4182(14) 0.2853(10) 0.4840(9) 0.036(4) Uani 1 1 d . . . H37B H -0.4893 0.2976 0.4746 0.054 Uiso 1 1 calc R . . H37G H -0.4138 0.3022 0.5238 0.054 Uiso 1 1 calc R . . H37H H -0.4113 0.2272 0.5027 0.054 Uiso 1 1 calc R . . N41B N 0.1490(9) 0.2502(8) 0.3333(7) 0.029(3) Uani 1 1 d . . . N42B N 0.3305(9) 0.3543(7) 0.2690(7) 0.021(3) Uani 1 1 d . . . C41B C 0.0650(12) 0.1961(10) 0.3611(9) 0.032(4) Uani 1 1 d . . . H41B H 0.0026 0.2130 0.3437 0.038 Uiso 1 1 calc R . . C42B C 0.0613(14) 0.1145(10) 0.4150(10) 0.043(5) Uani 1 1 d . . . H42B H -0.0003 0.0778 0.4313 0.051 Uiso 1 1 calc R . . C43B C 0.1497(13) 0.0895(9) 0.4435(10) 0.035(4) Uani 1 1 d . . . H43B H 0.1482 0.0363 0.4824 0.042 Uiso 1 1 calc R . . C44B C 0.2405(11) 0.1448(10) 0.4132(8) 0.029(4) Uani 1 1 d . . . C45B C 0.3391(13) 0.1229(10) 0.4379(9) 0.030(4) Uani 1 1 d . . . H45B H 0.3389 0.0704 0.4775 0.036 Uiso 1 1 calc R . . C46B C 0.4278(12) 0.1730(9) 0.4074(8) 0.027(3) Uani 1 1 d . . . H46B H 0.4908 0.1553 0.4237 0.032 Uiso 1 1 calc R . . C47B C 0.4308(12) 0.2558(9) 0.3486(9) 0.024(3) Uani 1 1 d . . . C48B C 0.5238(12) 0.3114(10) 0.3105(10) 0.030(4) Uani 1 1 d . . . H48B H 0.5899 0.2980 0.3236 0.036 Uiso 1 1 calc R . . C49B C 0.5170(12) 0.3856(9) 0.2537(9) 0.029(4) Uani 1 1 d . . . H49B H 0.5784 0.4248 0.2274 0.035 Uiso 1 1 calc R . . C50B C 0.4191(12) 0.4030(9) 0.2349(9) 0.025(3) Uani 1 1 d . . . H50B H 0.4174 0.4543 0.1941 0.030 Uiso 1 1 calc R . . C51B C 0.2383(11) 0.2241(9) 0.3599(9) 0.023(3) Uani 1 1 d . . . C52B C 0.3349(12) 0.2783(9) 0.3253(8) 0.025(3) Uani 1 1 d . . . C1C C -0.1832(18) 0.1775(12) 0.6210(14) 0.056(6) Uani 1 1 d . . . C2C C -0.2210(19) 0.1288(12) 0.5984(13) 0.056(6) Uani 1 1 d . . . H2C H -0.1771 0.1246 0.5520 0.067 Uiso 1 1 calc R . . C3C C -0.318(2) 0.0857(12) 0.6385(13) 0.058(6) Uani 1 1 d . . . H3C H -0.3383 0.0478 0.6229 0.070 Uiso 1 1 calc R . . C4C C -0.3884(18) 0.0944(12) 0.7005(11) 0.054(5) Uani 1 1 d . . . H4C H -0.4604 0.0674 0.7246 0.064 Uiso 1 1 calc R . . C5C C -0.356(2) 0.1420(14) 0.7285(15) 0.071(7) Uani 1 1 d . . . H5C H -0.4041 0.1462 0.7739 0.085 Uiso 1 1 calc R . . C6C C -0.249(2) 0.1864(14) 0.6886(16) 0.071(7) Uani 1 1 d . . . H6C H -0.2232 0.2198 0.7069 0.085 Uiso 1 1 calc R . . C7C C -0.068(2) 0.2248(18) 0.5762(17) 0.095(9) Uani 1 1 d . . . H7C H -0.0228 0.2087 0.6114 0.143 Uiso 1 1 calc R . . H8C H -0.0761 0.2828 0.5577 0.143 Uiso 1 1 calc R . . H9C H -0.0317 0.2130 0.5310 0.143 Uiso 1 1 calc R . . C1D C 0.3178(15) 0.3741(11) -0.1191(9) 0.037(4) Uani 1 1 d . . . C2D C 0.3450(15) 0.3316(12) -0.1646(11) 0.050(5) Uani 1 1 d . . . H2D H 0.2907 0.3185 -0.1822 0.060 Uiso 1 1 calc R . . C3D C 0.4489(19) 0.3083(16) -0.1843(13) 0.074(7) Uani 1 1 d . . . H3D H 0.4645 0.2787 -0.2151 0.088 Uiso 1 1 calc R . . C4D C 0.5313(17) 0.3255(16) -0.1621(12) 0.066(7) Uani 1 1 d . . . H4D H 0.6033 0.3091 -0.1772 0.079 Uiso 1 1 calc R . . C5D C 0.5063(16) 0.3670(13) -0.1175(11) 0.057(6) Uani 1 1 d . . . H5D H 0.5616 0.3795 -0.1004 0.069 Uiso 1 1 calc R . . C6D C 0.3999(17) 0.3918(11) -0.0961(11) 0.049(5) Uani 1 1 d . . . H6D H 0.3846 0.4212 -0.0652 0.059 Uiso 1 1 calc R . . C7D C 0.2024(17) 0.3963(14) -0.0939(12) 0.058(6) Uani 1 1 d . . . H7D H 0.2028 0.4549 -0.1122 0.087 Uiso 1 1 calc R . . H8D H 0.1721 0.3698 -0.0364 0.087 Uiso 1 1 calc R . . H9D H 0.1567 0.3785 -0.1165 0.087 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 Cu1A 0.0274(10) 0.0209(10) 0.0289(11) -0.0105(8) -0.0091(8) 0.0042(8) I1A 0.0296(5) 0.0241(5) 0.0312(6) -0.0092(5) -0.0158(5) 0.0041(4) P1A 0.034(2) 0.020(2) 0.028(2) -0.0088(18) -0.0005(18) 0.0010(17) C11A 0.044(11) 0.036(10) 0.066(14) -0.030(10) -0.008(10) 0.011(8) N11A 0.040(8) 0.016(7) 0.051(9) -0.009(7) -0.007(7) 0.004(6) C12A 0.033(9) 0.025(9) 0.035(10) 0.003(8) 0.000(8) 0.003(7) C13A 0.044(10) 0.020(8) 0.045(11) -0.008(8) -0.019(8) -0.002(7) N14A 0.049(9) 0.028(8) 0.042(9) -0.011(7) -0.018(7) 0.004(7) C15A 0.041(10) 0.023(8) 0.038(10) -0.008(8) -0.020(8) 0.009(7) C16A 0.034(9) 0.036(10) 0.044(11) -0.018(8) -0.016(8) 0.000(8) C17A 0.066(13) 0.028(10) 0.050(12) -0.017(9) -0.028(10) 0.010(9) C21A 0.049(11) 0.024(9) 0.032(10) -0.014(8) 0.007(8) -0.003(8) N21A 0.057(10) 0.027(8) 0.030(8) -0.017(7) -0.003(7) 0.002(7) C22A 0.077(14) 0.025(9) 0.045(11) -0.019(9) -0.017(10) 0.006(9) C23A 0.17(3) 0.047(13) 0.060(15) -0.035(12) -0.073(17) 0.028(15) N24A 0.35(4) 0.056(13) 0.095(17) -0.050(13) -0.16(2) 0.08(2) C25A 0.19(3) 0.048(14) 0.062(16) -0.028(12) -0.078(19) 0.028(17) C26A 0.16(2) 0.029(11) 0.019(10) -0.017(8) -0.013(12) 0.018(13) C27A 0.20(3) 0.057(16) 0.09(2) -0.032(15) -0.09(2) 0.012(19) C31A 0.035(9) 0.017(8) 0.053(11) -0.008(8) -0.012(8) 0.013(7) N31A 0.032(8) 0.021(7) 0.042(9) 0.000(6) -0.003(7) 0.007(6) C32A 0.046(11) 0.025(9) 0.050(12) -0.001(9) 0.007(9) 0.015(8) C33A 0.040(10) 0.032(10) 0.043(11) -0.007(9) 0.000(9) 0.006(8) N34A 0.025(7) 0.039(8) 0.035(8) -0.016(7) -0.004(6) 0.009(6) C35A 0.028(9) 0.027(9) 0.047(11) -0.013(8) -0.011(8) 0.004(7) C36A 0.029(9) 0.025(9) 0.063(12) -0.020(9) -0.018(9) 0.010(7) C37A 0.031(10) 0.053(12) 0.063(13) -0.005(10) -0.024(10) 0.014(9) N41A 0.021(7) 0.030(7) 0.028(7) -0.016(6) -0.011(5) 0.004(5) N42A 0.022(6) 0.040(8) 0.018(6) -0.017(6) -0.008(5) -0.002(6) C41A 0.026(8) 0.026(8) 0.035(9) -0.007(7) -0.024(7) 0.001(6) C42A 0.030(9) 0.028(9) 0.037(10) -0.017(8) -0.007(7) -0.013(7) C43A 0.027(9) 0.042(10) 0.032(9) -0.016(8) -0.010(7) 0.002(7) C44A 0.028(8) 0.035(9) 0.027(9) -0.016(8) -0.007(7) 0.007(7) C45A 0.026(8) 0.032(9) 0.034(9) -0.015(8) -0.012(7) 0.014(7) C47A 0.028(8) 0.018(7) 0.019(8) -0.008(6) -0.002(6) 0.013(6) C48A 0.024(8) 0.021(8) 0.048(11) -0.012(8) -0.010(8) 0.007(7) C49A 0.050(11) 0.011(7) 0.033(9) -0.004(7) -0.015(8) -0.009(7) C50A 0.033(9) 0.006(7) 0.041(10) -0.010(7) -0.010(7) 0.005(6) C51A 0.029(8) 0.026(8) 0.015(7) -0.013(6) -0.009(6) 0.003(6) C52A 0.025(8) 0.022(8) 0.023(8) 0.000(7) 0.006(7) 0.011(6) Cu1B 0.0229(10) 0.0239(10) 0.0334(11) -0.0074(9) -0.0120(8) 0.0018(8) I1B 0.0297(6) 0.0257(6) 0.0299(6) -0.0059(5) -0.0150(5) 0.0043(4) P1B 0.0200(19) 0.024(2) 0.027(2) -0.0073(17) -0.0083(17) -0.0003(16) C11B 0.031(9) 0.026(8) 0.035(9) -0.011(7) -0.012(7) 0.005(7) N11B 0.032(7) 0.020(7) 0.039(8) -0.008(6) -0.016(6) 0.004(6) C12B 0.040(10) 0.040(10) 0.040(11) -0.018(9) -0.008(8) -0.003(8) C13B 0.069(14) 0.033(10) 0.039(11) -0.016(9) 0.003(10) -0.007(9) N14B 0.048(9) 0.030(8) 0.042(9) -0.012(7) -0.007(7) 0.005(7) C15B 0.046(11) 0.058(13) 0.063(13) -0.030(11) -0.031(10) 0.023(10) C16B 0.037(10) 0.056(12) 0.042(10) -0.028(9) -0.027(8) 0.019(9) C17B 0.059(14) 0.032(11) 0.085(17) -0.010(11) 0.018(12) 0.008(10) C21B 0.026(8) 0.024(8) 0.047(10) -0.012(8) -0.014(8) 0.006(7) N21B 0.024(7) 0.029(7) 0.032(7) -0.008(6) -0.019(6) 0.004(6) C22B 0.038(10) 0.034(9) 0.042(10) -0.020(8) -0.022(8) 0.012(8) C23B 0.040(11) 0.062(13) 0.058(13) -0.046(11) -0.011(9) 0.006(9) N24B 0.049(9) 0.057(10) 0.047(9) -0.033(8) -0.036(8) 0.027(8) C25B 0.051(11) 0.049(11) 0.031(9) -0.017(9) -0.028(9) 0.025(9) C26B 0.032(9) 0.032(9) 0.037(10) -0.013(8) -0.011(8) 0.006(7) C27B 0.052(13) 0.103(18) 0.087(17) -0.070(15) -0.050(12) 0.031(12) C31B 0.025(8) 0.031(9) 0.031(9) -0.009(7) -0.012(7) 0.004(7) N31B 0.019(6) 0.024(7) 0.036(8) -0.014(6) -0.009(6) 0.001(5) C32B 0.023(8) 0.019(8) 0.045(10) -0.016(7) -0.014(7) 0.007(6) C33B 0.034(9) 0.024(8) 0.042(10) -0.023(8) -0.016(8) 0.009(7) N34B 0.031(7) 0.021(7) 0.035(8) -0.011(6) -0.006(6) 0.001(6) C35B 0.034(9) 0.030(9) 0.025(9) -0.009(7) -0.013(7) 0.002(7) C36B 0.031(9) 0.012(7) 0.043(10) -0.007(7) -0.023(8) 0.004(6) C37B 0.043(10) 0.035(10) 0.025(9) -0.015(8) 0.000(8) -0.007(8) N41B 0.011(6) 0.042(8) 0.031(8) -0.017(7) 0.003(5) -0.012(5) N42B 0.022(6) 0.020(6) 0.026(7) -0.010(6) -0.014(5) 0.006(5) C41B 0.019(8) 0.037(9) 0.035(9) -0.009(8) -0.012(7) -0.004(7) C42B 0.041(10) 0.022(9) 0.041(11) 0.014(8) -0.017(9) -0.012(8) C43B 0.036(9) 0.019(8) 0.033(9) -0.004(7) 0.002(8) -0.004(7) C44B 0.012(7) 0.042(10) 0.013(8) 0.005(7) 0.000(6) 0.001(7) C45B 0.035(9) 0.035(9) 0.019(8) -0.012(7) -0.009(7) 0.010(7) C46B 0.025(8) 0.029(9) 0.019(8) -0.004(7) -0.009(6) 0.005(7) C47B 0.021(8) 0.031(9) 0.022(8) -0.012(7) -0.011(6) 0.006(6) C48B 0.024(8) 0.038(10) 0.042(10) -0.026(8) -0.018(7) 0.011(7) C49B 0.021(8) 0.026(8) 0.039(10) -0.013(8) -0.006(7) -0.007(6) C50B 0.025(8) 0.016(7) 0.028(8) -0.005(7) -0.006(7) 0.001(6) C51B 0.013(7) 0.023(8) 0.035(9) -0.011(7) -0.010(6) 0.000(6) C52B 0.020(8) 0.031(9) 0.016(7) -0.007(7) 0.001(6) -0.002(6) C1C 0.068(14) 0.034(11) 0.071(15) -0.008(11) -0.047(13) 0.006(10) C2C 0.074(15) 0.040(12) 0.064(14) -0.018(11) -0.043(12) 0.012(11) C3C 0.086(17) 0.033(11) 0.054(14) -0.016(10) -0.023(12) 0.001(11) C4C 0.065(14) 0.048(12) 0.036(11) -0.004(10) -0.020(10) -0.004(10) C5C 0.085(18) 0.063(15) 0.070(16) -0.031(13) -0.030(14) 0.038(14) C6C 0.11(2) 0.056(14) 0.089(19) -0.044(14) -0.069(17) 0.038(14) C7C 0.062(16) 0.11(2) 0.11(2) -0.037(19) -0.048(16) 0.000(16) C1D 0.048(11) 0.046(11) 0.019(8) -0.012(8) -0.018(8) 0.002(8) C2D 0.042(11) 0.068(14) 0.041(11) -0.019(10) -0.026(9) 0.021(10) C3D 0.073(16) 0.12(2) 0.051(14) -0.050(15) -0.030(12) 0.042(15) C4D 0.041(12) 0.11(2) 0.044(13) -0.041(14) -0.006(10) 0.019(12) C5D 0.034(11) 0.072(15) 0.038(11) 0.001(11) -0.009(9) -0.003(10) C6D 0.066(14) 0.034(10) 0.039(11) -0.006(9) -0.019(10) -0.005(9) C7D 0.066(14) 0.074(15) 0.049(13) -0.033(12) -0.031(11) 0.020(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 Cu1A N42A 2.072(13) . ? Cu1A N41A 2.092(12) . ? Cu1A P1A 2.209(4) . ? Cu1A I1A 2.615(2) . ? P1A C21A 1.834(17) . ? P1A C11A 1.839(19) . ? P1A C31A 1.867(17) . ? C11A N11A 1.44(2) . ? C11A H11A 0.9900 . ? C11A H11E 0.9900 . ? N11A C12A 1.45(2) . ? N11A C16A 1.48(2) . ? C12A C13A 1.50(2) . ? C12A H12A 0.9900 . ? C12A H12E 0.9900 . ? C13A N14A 1.46(2) . ? C13A H13A 0.9900 . ? C13A H13E 0.9900 . ? N14A C15A 1.46(2) . ? N14A C17A 1.47(2) . ? C15A C16A 1.51(2) . ? C15A H15A 0.9900 . ? C15A H15E 0.9900 . ? C16A H16A 0.9900 . ? C16A H16E 0.9900 . ? C17A H17A 0.9800 . ? C17A H17E 0.9800 . ? C17A H17F 0.9800 . ? C21A N21A 1.43(2) . ? C21A H21A 0.9900 . ? C21A H21E 0.9900 . ? N21A C26A 1.46(2) . ? N21A C22A 1.47(2) . ? C22A C23A 1.49(3) . ? C22A H22A 0.9900 . ? C22A H22E 0.9900 . ? C23A N24A 1.43(3) . ? C23A H23A 0.9900 . ? C23A H23E 0.9900 . ? N24A C27A 1.26(3) . ? N24A C25A 1.47(3) . ? C25A C26A 1.44(3) . ? C25A H25A 0.9900 . ? C25A H25E 0.9900 . ? C26A H26A 0.9900 . ? C26A H26E 0.9900 . ? C27A H27A 0.9800 . ? C27A H27E 0.9800 . ? C27A H27F 0.9800 . ? C31A N31A 1.45(2) . ? C31A H31A 0.9900 . ? C31A H31E 0.9900 . ? N31A C32A 1.46(2) . ? N31A C36A 1.47(2) . ? C32A C33A 1.49(2) . ? C32A H32A 0.9900 . ? C32A H32E 0.9900 . ? C33A N34A 1.47(2) . ? C33A H33A 0.9900 . ? C33A H33E 0.9900 . ? N34A C35A 1.453(19) . ? N34A C37A 1.46(2) . ? C35A C36A 1.49(2) . ? C35A H35A 0.9900 . ? C35A H35E 0.9900 . ? C36A H36A 0.9900 . ? C36A H36E 0.9900 . ? C37A H37A 0.9800 . ? C37A H37E 0.9800 . ? C37A H37F 0.9800 . ? N41A C41A 1.332(18) . ? N41A C51A 1.371(18) . ? N42A C50A 1.312(18) . ? N42A C52A 1.379(19) . ? C41A C42A 1.42(2) . ? C41A H41A 0.9500 . ? C42A C43A 1.37(2) . ? C42A H42A 0.9500 . ? C43A C44A 1.41(2) . ? C43A H43A 0.9500 . ? C44A C51A 1.41(2) . ? C44A C45A 1.45(2) . ? C45A C46A 1.46(2) . ? C45A H45A 0.9500 . ? C46A C47A 1.37(2) . ? C46A H46A 0.9500 . ? C47A C48A 1.41(2) . ? C47A C52A 1.41(2) . ? C48A C49A 1.37(2) . ? C48A H48A 0.9500 . ? C49A C50A 1.39(2) . ? C49A H49A 0.9500 . ? C50A H50A 0.9500 . ? C51A C52A 1.45(2) . ? Cu1B N41B 2.063(13) . ? Cu1B N42B 2.085(11) . ? Cu1B P1B 2.197(4) . ? Cu1B I1B 2.619(2) . ? P1B C21B 1.816(17) . ? P1B C31B 1.836(15) . ? P1B C11B 1.843(16) . ? C11B N11B 1.472(19) . ? C11B H11B 0.9900 . ? C11B H11G 0.9900 . ? N11B C12B 1.45(2) . ? N11B C16B 1.45(2) . ? C12B C13B 1.51(2) . ? C12B H12B 0.9900 . ? C12B H12G 0.9900 . ? C13B N14B 1.44(2) . ? C13B H13B 0.9900 . ? C13B H13G 0.9900 . ? N14B C17B 1.47(2) . ? N14B C15B 1.47(2) . ? C15B C16B 1.50(2) . ? C15B H15B 0.9900 . ? C15B H15G 0.9900 . ? C16B H16B 0.9900 . ? C16B H16G 0.9900 . ? C17B H17B 0.9800 . ? C17B H17G 0.9800 . ? C17B H17H 0.9800 . ? C21B N21B 1.459(19) . ? C21B H21B 0.9900 . ? C21B H21G 0.9900 . ? N21B C26B 1.466(19) . ? N21B C22B 1.49(2) . ? C22B C23B 1.51(2) . ? C22B H22B 0.9900 . ? C22B H22G 0.9900 . ? C23B N24B 1.43(2) . ? C23B H23B 0.9900 . ? C23B H23G 0.9900 . ? N24B C27B 1.46(2) . ? N24B C25B 1.48(2) . ? C25B C26B 1.51(2) . ? C25B H25B 0.9900 . ? C25B H25G 0.9900 . ? C26B H26B 0.9900 . ? C26B H26G 0.9900 . ? C27B H27B 0.9800 . ? C27B H27G 0.9800 . ? C27B H27H 0.9800 . ? C31B N31B 1.432(19) . ? C31B H31B 0.9900 . ? C31B H31G 0.9900 . ? N31B C32B 1.453(18) . ? N31B C36B 1.491(18) . ? C32B C33B 1.50(2) . ? C32B H32B 0.9900 . ? C32B H32G 0.9900 . ? C33B N34B 1.461(19) . ? C33B H33B 0.9900 . ? C33B H33G 0.9900 . ? N34B C37B 1.439(19) . ? N34B C35B 1.466(19) . ? C35B C36B 1.49(2) . ? C35B H35B 0.9900 . ? C35B H35G 0.9900 . ? C36B H36B 0.9900 . ? C36B H36G 0.9900 . ? C37B H37B 0.9800 . ? C37B H37G 0.9800 . ? C37B H37H 0.9800 . ? N41B C41B 1.320(19) . ? N41B C51B 1.380(18) . ? N42B C50B 1.294(18) . ? N42B C52B 1.380(18) . ? C41B C42B 1.42(2) . ? C41B H41B 0.9500 . ? C42B C43B 1.39(2) . ? C42B H42B 0.9500 . ? C43B C44B 1.39(2) . ? C43B H43B 0.9500 . ? C44B C51B 1.39(2) . ? C44B C45B 1.47(2) . ? C45B C46B 1.31(2) . ? C45B H45B 0.9500 . ? C46B C47B 1.46(2) . ? C46B H46B 0.9500 . ? C47B C48B 1.40(2) . ? C47B C52B 1.42(2) . ? C48B C49B 1.37(2) . ? C48B H48B 0.9500 . ? C49B C50B 1.40(2) . ? C49B H49B 0.9500 . ? C50B H50B 0.9500 . ? C51B C52B 1.43(2) . ? C1C C2C 1.33(3) . ? C1C C6C 1.41(3) . ? C1C C7C 1.55(3) . ? C2C C3C 1.33(3) . ? C2C H2C 0.9500 . ? C3C C4C 1.35(3) . ? C3C H3C 0.9500 . ? C4C C5C 1.36(3) . ? C4C H4C 0.9500 . ? C5C C6C 1.45(3) . ? C5C H5C 0.9500 . ? C6C H6C 0.9500 . ? C7C H7C 0.9800 . ? C7C H8C 0.9800 . ? C7C H9C 0.9800 . ? C1D C6D 1.37(2) . ? C1D C2D 1.39(3) . ? C1D C7D 1.50(3) . ? C2D C3D 1.36(3) . ? C2D H2D 0.9500 . ? C3D C4D 1.36(3) . ? C3D H3D 0.9500 . ? C4D C5D 1.36(3) . ? C4D H4D 0.9500 . ? C5D C6D 1.41(3) . ? C5D H5D 0.9500 . ? C6D H6D 0.9500 . ? C7D H7D 0.9800 . ? C7D H8D 0.9800 . ? C7D H9D 0.9800 . ? 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 N42A Cu1A N41A 80.8(5) . . ? N42A Cu1A P1A 130.1(4) . . ? N41A Cu1A P1A 115.4(4) . . ? N42A Cu1A I1A 109.8(3) . . ? N41A Cu1A I1A 118.1(3) . . ? P1A Cu1A I1A 102.80(14) . . ? C21A P1A C11A 101.6(8) . . ? C21A P1A C31A 99.9(8) . . ? C11A P1A C31A 99.6(8) . . ? C21A P1A Cu1A 124.9(6) . . ? C11A P1A Cu1A 109.5(6) . . ? C31A P1A Cu1A 117.5(6) . . ? N11A C11A P1A 114.6(13) . . ? N11A C11A H11A 108.6 . . ? P1A C11A H11A 108.6 . . ? N11A C11A H11E 108.6 . . ? P1A C11A H11E 108.6 . . ? H11A C11A H11E 107.6 . . ? C12A N11A C11A 112.3(14) . . ? C12A N11A C16A 109.1(13) . . ? C11A N11A C16A 114.9(15) . . ? N11A C12A C13A 111.6(14) . . ? N11A C12A H12A 109.3 . . ? C13A C12A H12A 109.3 . . ? N11A C12A H12E 109.3 . . ? C13A C12A H12E 109.3 . . ? H12A C12A H12E 108.0 . . ? N14A C13A C12A 110.9(15) . . ? N14A C13A H13A 109.5 . . ? C12A C13A H13A 109.5 . . ? N14A C13A H13E 109.5 . . ? C12A C13A H13E 109.5 . . ? H13A C13A H13E 108.0 . . ? C13A N14A C15A 110.1(13) . . ? C13A N14A C17A 109.7(14) . . ? C15A N14A C17A 110.9(14) . . ? N14A C15A C16A 109.7(13) . . ? N14A C15A H15A 109.7 . . ? C16A C15A H15A 109.7 . . ? N14A C15A H15E 109.7 . . ? C16A C15A H15E 109.7 . . ? H15A C15A H15E 108.2 . . ? N11A C16A C15A 108.9(14) . . ? N11A C16A H16A 109.9 . . ? C15A C16A H16A 109.9 . . ? N11A C16A H16E 109.9 . . ? C15A C16A H16E 109.9 . . ? H16A C16A H16E 108.3 . . ? N14A C17A H17A 109.5 . . ? N14A C17A H17E 109.5 . . ? H17A C17A H17E 109.5 . . ? N14A C17A H17F 109.5 . . ? H17A C17A H17F 109.5 . . ? H17E C17A H17F 109.5 . . ? N21A C21A P1A 114.5(11) . . ? N21A C21A H21A 108.6 . . ? P1A C21A H21A 108.6 . . ? N21A C21A H21E 108.6 . . ? P1A C21A H21E 108.6 . . ? H21A C21A H21E 107.6 . . ? C21A N21A C26A 112.3(16) . . ? C21A N21A C22A 109.8(14) . . ? C26A N21A C22A 108.4(14) . . ? N21A C22A C23A 109.8(16) . . ? N21A C22A H22A 109.7 . . ? C23A C22A H22A 109.7 . . ? N21A C22A H22E 109.7 . . ? C23A C22A H22E 109.7 . . ? H22A C22A H22E 108.2 . . ? N24A C23A C22A 111(2) . . ? N24A C23A H23A 109.5 . . ? C22A C23A H23A 109.5 . . ? N24A C23A H23E 109.5 . . ? C22A C23A H23E 109.5 . . ? H23A C23A H23E 108.1 . . ? C27A N24A C23A 120(2) . . ? C27A N24A C25A 119(2) . . ? C23A N24A C25A 109.8(18) . . ? C26A C25A N24A 109(2) . . ? C26A C25A H25A 109.9 . . ? N24A C25A H25A 109.9 . . ? C26A C25A H25E 109.9 . . ? N24A C25A H25E 109.9 . . ? H25A C25A H25E 108.3 . . ? C25A C26A N21A 114(2) . . ? C25A C26A H26A 108.6 . . ? N21A C26A H26A 108.6 . . ? C25A C26A H26E 108.6 . . ? N21A C26A H26E 108.6 . . ? H26A C26A H26E 107.6 . . ? N24A C27A H27A 109.5 . . ? N24A C27A H27E 109.5 . . ? H27A C27A H27E 109.5 . . ? N24A C27A H27F 109.5 . . ? H27A C27A H27F 109.5 . . ? H27E C27A H27F 109.5 . . ? N31A C31A P1A 113.8(12) . . ? N31A C31A H31A 108.8 . . ? P1A C31A H31A 108.8 . . ? N31A C31A H31E 108.8 . . ? P1A C31A H31E 108.8 . . ? H31A C31A H31E 107.7 . . ? C32A N31A C31A 112.7(13) . . ? C32A N31A C36A 109.9(14) . . ? C31A N31A C36A 111.7(13) . . ? N31A C32A C33A 110.4(15) . . ? N31A C32A H32A 109.6 . . ? C33A C32A H32A 109.6 . . ? N31A C32A H32E 109.6 . . ? C33A C32A H32E 109.6 . . ? H32A C32A H32E 108.1 . . ? N34A C33A C32A 109.3(14) . . ? N34A C33A H33A 109.8 . . ? C32A C33A H33A 109.8 . . ? N34A C33A H33E 109.8 . . ? C32A C33A H33E 109.8 . . ? H33A C33A H33E 108.3 . . ? C35A N34A C37A 110.2(13) . . ? C35A N34A C33A 107.6(13) . . ? C37A N34A C33A 110.0(14) . . ? N34A C35A C36A 113.3(14) . . ? N34A C35A H35A 108.9 . . ? C36A C35A H35A 108.9 . . ? N34A C35A H35E 108.9 . . ? C36A C35A H35E 108.9 . . ? H35A C35A H35E 107.7 . . ? N31A C36A C35A 109.6(14) . . ? N31A C36A H36A 109.8 . . ? C35A C36A H36A 109.8 . . ? N31A C36A H36E 109.8 . . ? C35A C36A H36E 109.8 . . ? H36A C36A H36E 108.2 . . ? N34A C37A H37A 109.5 . . ? N34A C37A H37E 109.5 . . ? H37A C37A H37E 109.5 . . ? N34A C37A H37F 109.5 . . ? H37A C37A H37F 109.5 . . ? H37E C37A H37F 109.5 . . ? C41A N41A C51A 117.3(12) . . ? C41A N41A Cu1A 130.8(10) . . ? C51A N41A Cu1A 111.6(9) . . ? C50A N42A C52A 115.7(13) . . ? C50A N42A Cu1A 131.0(10) . . ? C52A N42A Cu1A 113.3(9) . . ? N41A C41A C42A 123.7(14) . . ? N41A C41A H41A 118.1 . . ? C42A C41A H41A 118.1 . . ? C43A C42A C41A 119.1(14) . . ? C43A C42A H42A 120.5 . . ? C41A C42A H42A 120.5 . . ? C42A C43A C44A 118.7(15) . . ? C42A C43A H43A 120.6 . . ? C44A C43A H43A 120.6 . . ? C51A C44A C43A 118.8(14) . . ? C51A C44A C45A 119.2(14) . . ? C43A C44A C45A 122.0(14) . . ? C44A C45A C46A 119.9(14) . . ? C44A C45A H45A 120.1 . . ? C46A C45A H45A 120.1 . . ? C47A C46A C45A 118.7(14) . . ? C47A C46A H46A 120.7 . . ? C45A C46A H46A 120.7 . . ? C46A C47A C48A 121.8(14) . . ? C46A C47A C52A 122.5(15) . . ? C48A C47A C52A 115.5(14) . . ? C49A C48A C47A 120.4(14) . . ? C49A C48A H48A 119.8 . . ? C47A C48A H48A 119.8 . . ? C48A C49A C50A 118.8(15) . . ? C48A C49A H49A 120.6 . . ? C50A C49A H49A 120.6 . . ? N42A C50A C49A 124.8(15) . . ? N42A C50A H50A 117.6 . . ? C49A C50A H50A 117.6 . . ? N41A C51A C44A 122.3(13) . . ? N41A C51A C52A 118.0(12) . . ? C44A C51A C52A 119.6(13) . . ? N42A C52A C47A 124.6(14) . . ? N42A C52A C51A 115.8(13) . . ? C47A C52A C51A 119.6(14) . . ? N41B Cu1B N42B 81.3(5) . . ? N41B Cu1B P1B 131.9(4) . . ? N42B Cu1B P1B 121.6(3) . . ? N41B Cu1B I1B 108.4(4) . . ? N42B Cu1B I1B 107.9(3) . . ? P1B Cu1B I1B 103.52(14) . . ? C21B P1B C31B 100.0(7) . . ? C21B P1B C11B 100.2(8) . . ? C31B P1B C11B 101.5(7) . . ? C21B P1B Cu1B 126.1(5) . . ? C31B P1B Cu1B 117.0(6) . . ? C11B P1B Cu1B 108.3(5) . . ? N11B C11B P1B 114.8(11) . . ? N11B C11B H11B 108.6 . . ? P1B C11B H11B 108.6 . . ? N11B C11B H11G 108.6 . . ? P1B C11B H11G 108.6 . . ? H11B C11B H11G 107.5 . . ? C12B N11B C16B 109.4(13) . . ? C12B N11B C11B 112.6(13) . . ? C16B N11B C11B 114.4(13) . . ? N11B C12B C13B 111.1(15) . . ? N11B C12B H12B 109.4 . . ? C13B C12B H12B 109.4 . . ? N11B C12B H12G 109.4 . . ? C13B C12B H12G 109.4 . . ? H12B C12B H12G 108.0 . . ? N14B C13B C12B 109.7(15) . . ? N14B C13B H13B 109.7 . . ? C12B C13B H13B 109.7 . . ? N14B C13B H13G 109.7 . . ? C12B C13B H13G 109.7 . . ? H13B C13B H13G 108.2 . . ? C13B N14B C17B 111.1(17) . . ? C13B N14B C15B 111.7(14) . . ? C17B N14B C15B 110.9(16) . . ? N14B C15B C16B 110.8(15) . . ? N14B C15B H15B 109.5 . . ? C16B C15B H15B 109.5 . . ? N14B C15B H15G 109.5 . . ? C16B C15B H15G 109.5 . . ? H15B C15B H15G 108.1 . . ? N11B C16B C15B 109.5(14) . . ? N11B C16B H16B 109.8 . . ? C15B C16B H16B 109.8 . . ? N11B C16B H16G 109.8 . . ? C15B C16B H16G 109.8 . . ? H16B C16B H16G 108.2 . . ? N14B C17B H17B 109.5 . . ? N14B C17B H17G 109.5 . . ? H17B C17B H17G 109.5 . . ? N14B C17B H17H 109.5 . . ? H17B C17B H17H 109.5 . . ? H17G C17B H17H 109.5 . . ? N21B C21B P1B 111.5(11) . . ? N21B C21B H21B 109.3 . . ? P1B C21B H21B 109.3 . . ? N21B C21B H21G 109.3 . . ? P1B C21B H21G 109.3 . . ? H21B C21B H21G 108.0 . . ? C21B N21B C26B 111.8(12) . . ? C21B N21B C22B 113.7(12) . . ? C26B N21B C22B 108.0(12) . . ? N21B C22B C23B 108.4(13) . . ? N21B C22B H22B 110.0 . . ? C23B C22B H22B 110.0 . . ? N21B C22B H22G 110.0 . . ? C23B C22B H22G 110.0 . . ? H22B C22B H22G 108.4 . . ? N24B C23B C22B 112.5(16) . . ? N24B C23B H23B 109.1 . . ? C22B C23B H23B 109.1 . . ? N24B C23B H23G 109.1 . . ? C22B C23B H23G 109.1 . . ? H23B C23B H23G 107.8 . . ? C23B N24B C27B 111.1(16) . . ? C23B N24B C25B 110.7(13) . . ? C27B N24B C25B 109.7(14) . . ? N24B C25B C26B 111.8(14) . . ? N24B C25B H25B 109.3 . . ? C26B C25B H25B 109.3 . . ? N24B C25B H25G 109.3 . . ? C26B C25B H25G 109.3 . . ? H25B C25B H25G 107.9 . . ? N21B C26B C25B 109.9(13) . . ? N21B C26B H26B 109.7 . . ? C25B C26B H26B 109.7 . . ? N21B C26B H26G 109.7 . . ? C25B C26B H26G 109.7 . . ? H26B C26B H26G 108.2 . . ? N24B C27B H27B 109.5 . . ? N24B C27B H27G 109.5 . . ? H27B C27B H27G 109.5 . . ? N24B C27B H27H 109.5 . . ? H27B C27B H27H 109.5 . . ? H27G C27B H27H 109.5 . . ? N31B C31B P1B 113.9(11) . . ? N31B C31B H31B 108.8 . . ? P1B C31B H31B 108.8 . . ? N31B C31B H31G 108.8 . . ? P1B C31B H31G 108.8 . . ? H31B C31B H31G 107.7 . . ? C31B N31B C32B 112.8(12) . . ? C31B N31B C36B 113.0(12) . . ? C32B N31B C36B 107.4(11) . . ? N31B C32B C33B 112.2(13) . . ? N31B C32B H32B 109.2 . . ? C33B C32B H32B 109.2 . . ? N31B C32B H32G 109.2 . . ? C33B C32B H32G 109.2 . . ? H32B C32B H32G 107.9 . . ? N34B C33B C32B 109.5(12) . . ? N34B C33B H33B 109.8 . . ? C32B C33B H33B 109.8 . . ? N34B C33B H33G 109.8 . . ? C32B C33B H33G 109.8 . . ? H33B C33B H33G 108.2 . . ? C37B N34B C33B 113.1(13) . . ? C37B N34B C35B 111.0(13) . . ? C33B N34B C35B 108.8(12) . . ? N34B C35B C36B 111.2(12) . . ? N34B C35B H35B 109.4 . . ? C36B C35B H35B 109.4 . . ? N34B C35B H35G 109.4 . . ? C36B C35B H35G 109.4 . . ? H35B C35B H35G 108.0 . . ? C35B C36B N31B 110.9(13) . . ? C35B C36B H36B 109.5 . . ? N31B C36B H36B 109.5 . . ? C35B C36B H36G 109.5 . . ? N31B C36B H36G 109.5 . . ? H36B C36B H36G 108.1 . . ? N34B C37B H37B 109.5 . . ? N34B C37B H37G 109.5 . . ? H37B C37B H37G 109.5 . . ? N34B C37B H37H 109.5 . . ? H37B C37B H37H 109.5 . . ? H37G C37B H37H 109.5 . . ? C41B N41B C51B 116.6(14) . . ? C41B N41B Cu1B 131.7(11) . . ? C51B N41B Cu1B 111.7(9) . . ? C50B N42B C52B 117.5(12) . . ? C50B N42B Cu1B 130.8(10) . . ? C52B N42B Cu1B 111.7(9) . . ? N41B C41B C42B 124.5(15) . . ? N41B C41B H41B 117.8 . . ? C42B C41B H41B 117.8 . . ? C43B C42B C41B 118.6(15) . . ? C43B C42B H42B 120.7 . . ? C41B C42B H42B 120.7 . . ? C42B C43B C44B 117.8(14) . . ? C42B C43B H43B 121.1 . . ? C44B C43B H43B 121.1 . . ? C51B C44B C43B 120.3(13) . . ? C51B C44B C45B 118.1(14) . . ? C43B C44B C45B 121.6(14) . . ? C46B C45B C44B 122.6(15) . . ? C46B C45B H45B 118.7 . . ? C44B C45B H45B 118.7 . . ? C45B C46B C47B 121.0(14) . . ? C45B C46B H46B 119.5 . . ? C47B C46B H46B 119.5 . . ? C48B C47B C52B 118.5(14) . . ? C48B C47B C46B 124.4(13) . . ? C52B C47B C46B 116.9(13) . . ? C49B C48B C47B 118.4(14) . . ? C49B C48B H48B 120.8 . . ? C47B C48B H48B 120.8 . . ? C48B C49B C50B 119.4(14) . . ? C48B C49B H49B 120.3 . . ? C50B C49B H49B 120.3 . . ? N42B C50B C49B 124.7(14) . . ? N42B C50B H50B 117.7 . . ? C49B C50B H50B 117.7 . . ? N41B C51B C44B 122.2(13) . . ? N41B C51B C52B 118.1(13) . . ? C44B C51B C52B 119.4(13) . . ? N42B C52B C47B 121.4(13) . . ? N42B C52B C51B 116.9(13) . . ? C47B C52B C51B 121.7(14) . . ? C2C C1C C6C 120(2) . . ? C2C C1C C7C 122(2) . . ? C6C C1C C7C 118(2) . . ? C1C C2C C3C 122(2) . . ? C1C C2C H2C 118.8 . . ? C3C C2C H2C 118.8 . . ? C2C C3C C4C 122(2) . . ? C2C C3C H3C 119.2 . . ? C4C C3C H3C 119.2 . . ? C3C C4C C5C 120(2) . . ? C3C C4C H4C 120.1 . . ? C5C C4C H4C 120.1 . . ? C4C C5C C6C 119(2) . . ? C4C C5C H5C 120.3 . . ? C6C C5C H5C 120.3 . . ? C1C C6C C5C 117(2) . . ? C1C C6C H6C 121.7 . . ? C5C C6C H6C 121.7 . . ? C1C C7C H7C 109.5 . . ? C1C C7C H8C 109.5 . . ? H7C C7C H8C 109.5 . . ? C1C C7C H9C 109.5 . . ? H7C C7C H9C 109.5 . . ? H8C C7C H9C 109.5 . . ? C6D C1D C2D 117.0(18) . . ? C6D C1D C7D 122.2(17) . . ? C2D C1D C7D 120.7(16) . . ? C3D C2D C1D 121(2) . . ? C3D C2D H2D 119.7 . . ? C1D C2D H2D 119.7 . . ? C4D C3D C2D 123(2) . . ? C4D C3D H3D 118.4 . . ? C2D C3D H3D 118.4 . . ? C5D C4D C3D 117(2) . . ? C5D C4D H4D 121.4 . . ? C3D C4D H4D 121.4 . . ? C4D C5D C6D 121(2) . . ? C4D C5D H5D 119.5 . . ? C6D C5D H5D 119.5 . . ? C1D C6D C5D 121(2) . . ? C1D C6D H6D 119.5 . . ? C5D C6D H6D 119.5 . . ? C1D C7D H7D 109.5 . . ? C1D C7D H8D 109.5 . . ? H7D C7D H8D 109.5 . . ? C1D C7D H9D 109.5 . . ? H7D C7D H9D 109.5 . . ? H8D C7D H9D 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 3.328 _refine_diff_density_min -1.088 _refine_diff_density_rms 0.196 # start Validation Reply Form _vrf_PLAT220_star15a ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.00 Ratio RESPONSE: small size of the crystal along with not good quality of data collection resulted in no satisfactory solution of the problem. ; _vrf_PLAT316_star15a ; PROBLEM: Too many H on C in C=N Moiety in Main Residue .. C27A RESPONSE: On the C27A atom it steps out probable disorder. Small size of the crystalalong with not good quality of data collection resulted in no satisfactory solution of the problem. ; #_publ_author_letter #; #Please consider this CIF as deposit in the Cambridge #Crystallographic Data Centre #; #================================================ # Attachment 'star21.cif' data_star21 _database_code_depnum_ccdc_archive 'CCDC 747841' #TrackingRef 'star21.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'tris((4-ethylpiperazin-1-yl)methyl)phosphine' ; _chemical_name_common tris((4-ethylpiperazin-1-yl)methyl)phosphine _chemical_melting_point ? _chemical_formula_moiety 'C21 H45 N6 P' _chemical_formula_sum 'C21 H45 N6 P' _chemical_formula_weight 412.60 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M 'R 3 c' _symmetry_space_group_name_Hall 'R 3 -2"c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-y, -x, z+1/2' '-x+y, y, z+1/2' 'x, x-y, z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' '-y+2/3, -x+1/3, z+5/6' '-x+y+2/3, y+1/3, z+5/6' 'x+2/3, x-y+1/3, z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-y+1/3, -x+2/3, z+7/6' '-x+y+1/3, y+2/3, z+7/6' 'x+1/3, x-y+2/3, z+7/6' _cell_length_a 20.691(4) _cell_length_b 20.691(3) _cell_length_c 9.996(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3706(2) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 691 _cell_measurement_theta_min 3.41 _cell_measurement_theta_max 25.13 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.109 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.876 _exptl_absorpt_correction_T_max 0.910 _exptl_absorpt_process_details 'Oxford Diffraction, CrysAlis 1.171.30' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KM4-CCD _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9762 _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 25.13 _reflns_number_total 1306 _reflns_number_gt 1176 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, date)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, date)' _computing_data_reduction 'CrysAlis RED ' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXL-97 _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^)+(0.0336P)^2^+1.3624P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_number_reflns 1306 _refine_ls_number_parameters 86 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0337 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0643 _refine_ls_wR_factor_gt 0.0612 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.050 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.3333 0.6667 0.09079(9) 0.02360(17) Uani 1 3 d S . . N11 N 0.21807(7) 0.52372(7) 0.14594(14) 0.0231(3) Uani 1 1 d . . . C11 C 0.24654(9) 0.60203(8) 0.18204(18) 0.0254(4) Uani 1 1 d . . . H11A H 0.2565 0.6082 0.2794 0.030 Uiso 1 1 calc R . . H11B H 0.2078 0.6155 0.1623 0.030 Uiso 1 1 calc R . . C12 C 0.19024(10) 0.50759(10) 0.00882(18) 0.0278(4) Uani 1 1 d . . . H12A H 0.2306 0.5402 -0.0537 0.033 Uiso 1 1 calc R . . H12B H 0.1488 0.5181 -0.0016 0.033 Uiso 1 1 calc R . . C13 C 0.16284(9) 0.42635(9) -0.02513(19) 0.0269(4) Uani 1 1 d . . . H13A H 0.1453 0.4165 -0.1190 0.032 Uiso 1 1 calc R . . H13B H 0.2044 0.4159 -0.0160 0.032 Uiso 1 1 calc R . . N14 N 0.10168(8) 0.37726(8) 0.06451(16) 0.0264(3) Uani 1 1 d . . . C15 C 0.12904(9) 0.39329(9) 0.20188(18) 0.0286(4) Uani 1 1 d . . . H15A H 0.1699 0.3820 0.2131 0.034 Uiso 1 1 calc R . . H15B H 0.0882 0.3609 0.2639 0.034 Uiso 1 1 calc R . . C16 C 0.15731(9) 0.47426(9) 0.23648(19) 0.0265(4) Uani 1 1 d . . . H16A H 0.1159 0.4850 0.2293 0.032 Uiso 1 1 calc R . . H16B H 0.1756 0.4838 0.3300 0.032 Uiso 1 1 calc R . . C17 C 0.07485(10) 0.29853(10) 0.0330(2) 0.0349(4) Uani 1 1 d . . . H17A H 0.0418 0.2672 0.1061 0.042 Uiso 1 1 calc R . . H17B H 0.1181 0.2905 0.0296 0.042 Uiso 1 1 calc R . . C18 C 0.03282(12) 0.27289(11) -0.0980(2) 0.0462(6) Uani 1 1 d . . . H18A H -0.0070 0.2854 -0.0995 0.069 Uiso 1 1 calc R . . H18B H 0.0111 0.2188 -0.1067 0.069 Uiso 1 1 calc R . . H18C H 0.0672 0.2979 -0.1724 0.069 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 P1 0.0219(2) 0.0219(2) 0.0270(4) 0.000 0.000 0.01094(11) N11 0.0229(7) 0.0202(7) 0.0240(8) -0.0003(6) 0.0012(6) 0.0092(6) C11 0.0210(8) 0.0244(8) 0.0303(10) -0.0020(7) -0.0005(7) 0.0111(7) C12 0.0299(9) 0.0260(9) 0.0256(10) 0.0026(8) 0.0007(8) 0.0125(8) C13 0.0247(9) 0.0267(9) 0.0279(10) -0.0013(8) -0.0012(7) 0.0118(7) N14 0.0222(7) 0.0226(7) 0.0317(9) 0.0002(6) -0.0023(6) 0.0092(6) C15 0.0253(9) 0.0251(9) 0.0308(11) 0.0053(8) 0.0014(8) 0.0091(7) C16 0.0244(9) 0.0296(9) 0.0250(10) 0.0029(8) 0.0028(8) 0.0131(8) C17 0.0308(9) 0.0235(9) 0.0463(13) -0.0004(8) -0.0033(9) 0.0105(8) C18 0.0470(12) 0.0274(10) 0.0583(16) -0.0121(10) -0.0168(11) 0.0142(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 P1 C11 1.8558(17) 2_665 ? P1 C11 1.8558(17) . ? P1 C11 1.8558(17) 3_565 ? N11 C12 1.459(2) . ? N11 C11 1.466(2) . ? N11 C16 1.470(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.520(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N14 1.466(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? N14 C15 1.459(2) . ? N14 C17 1.469(2) . ? C15 C16 1.513(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.513(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 P1 C11 97.91(8) 2_665 . ? C11 P1 C11 97.91(8) 2_665 3_565 ? C11 P1 C11 97.91(8) . 3_565 ? C12 N11 C11 112.25(13) . . ? C12 N11 C16 108.47(14) . . ? C11 N11 C16 110.45(13) . . ? N11 C11 P1 112.64(12) . . ? N11 C11 H11A 109.1 . . ? P1 C11 H11A 109.1 . . ? N11 C11 H11B 109.1 . . ? P1 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? N11 C12 C13 110.43(14) . . ? N11 C12 H12A 109.6 . . ? C13 C12 H12A 109.6 . . ? N11 C12 H12B 109.6 . . ? C13 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? N14 C13 C12 110.19(14) . . ? 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 . . ? C15 N14 C13 108.38(13) . . ? C15 N14 C17 110.05(14) . . ? C13 N14 C17 110.71(15) . . ? N14 C15 C16 110.99(14) . . ? N14 C15 H15A 109.4 . . ? C16 C15 H15A 109.4 . . ? N14 C15 H15B 109.4 . . ? C16 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? N11 C16 C15 110.66(14) . . ? N11 C16 H16A 109.5 . . ? C15 C16 H16A 109.5 . . ? N11 C16 H16B 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? N14 C17 C18 114.02(17) . . ? N14 C17 H17A 108.7 . . ? C18 C17 H17A 108.7 . . ? N14 C17 H17B 108.7 . . ? C18 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C12 N11 C11 P1 -68.46(16) . . . . ? C16 N11 C11 P1 170.36(11) . . . . ? C11 P1 C11 N11 -73.21(17) 2_665 . . . ? C11 P1 C11 N11 -172.39(11) 3_565 . . . ? C11 N11 C12 C13 178.82(13) . . . . ? C16 N11 C12 C13 -58.87(17) . . . . ? N11 C12 C13 N14 60.67(19) . . . . ? C12 C13 N14 C15 -59.04(18) . . . . ? C12 C13 N14 C17 -179.83(14) . . . . ? C13 N14 C15 C16 58.56(17) . . . . ? C17 N14 C15 C16 179.76(14) . . . . ? C12 N11 C16 C15 58.04(17) . . . . ? C11 N11 C16 C15 -178.55(14) . . . . ? N14 C15 C16 N11 -59.14(18) . . . . ? C15 N14 C17 C18 169.62(16) . . . . ? C13 N14 C17 C18 -70.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.191 _refine_diff_density_min -0.120 _refine_diff_density_rms 0.028